Probing the shapes of chiral bis-(o-naphthalimidobenzoyl) systems using X-ray and circular dichroism methods

Rychlewska, U.; Plutecka, A.; Hoffmann, M.; Skowronek, P.; Gawrońska, K.; Gawroński, J.

doi:10.1107/S0108768108041827

Probing the shapes of chiral bis-(o-naphthalimidobenzoyl) systems using X-ray and circular dichroism methods

U. Rychlewska, A. Plutecka, M. Hoffmann, P. Skowronek, K. Gawrońska and J. Gawroński

CD (circular dichroism) and X-ray investigations have been carried out in order to identify the prevalent conformations and define the forces that determine the molecular and supramolecular organization of the alkyl-bridged bichromophoric [NAB, ortho-(1,8-naphthalimido)benzoyl] units, each consisting of the benzoyl substituted in the ortho position with the 1,8-naphthalimide group. The results reveal that NAB bichromophores incorporated into the same molecule exist in a variety of conformation/helicity combinations. The molecular structures are largely stabilized by local 1,3-CH/CO dipole–dipole interactions, while the crystal packing besides dispersive H

H interactions is mostly governed by multiple C—H

O(=C) and C—H

π interactions. The relatively small contribution of π

π interactions comes from a pairwise off-face stacking between naphthalimide rings or from pairwise carbonyl

π interactions. All these types of intermolecular interactions have been summarized quantitatively by means of a Hirshfeld surface analysis.

Keywords: 1,8-naphthalimides; chiral diols and amines; weak hydrogen bonds; dipole–dipole interactions; circular dichroism.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768108041827/so5018sup1.cif Contains datablocks 1, 2, 3, 4
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768108041827/so50181sup2.hkl Contains datablock 1
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768108041827/so50182sup3.hkl Contains datablock 2
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768108041827/so50183sup4.hkl Contains datablock 3
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768108041827/so50184sup5.hkl Contains datablock 4

CCDC references: 722693; 722694; 722695; 722696

Computing details top

Data collection: CrysAlis CCD v.1.171.32.5(Oxford Diffraction,2007) for (1); CrysAlis CCD v.1.171.23(Oxford Diffraction,2002) for (2), (3), (4). Cell refinement: CrysAlis RED v.1.171.32.5(Oxford Diffraction,2007) for (1); CrysAlis RED v.1.171.23(Oxford Diffraction,2002) for (2), (3), (4). Data reduction: CrysAlis RED v.1.171.32.5(Oxford Diffraction,2007) for (1); CrysAlis RED v.1.171.23(Oxford Diffraction,2002) for (2), (3), (4). For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP. Simens Analytical X-Ray Instruments (1989); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

(1) top

Crystal data top

C₄₁H₂₆N₂O₈	F(000) = 1400
M_r = 674.64	D_x = 1.457 Mg m⁻³
Monoclinic, C2	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: C 2y	Cell parameters from 10320 reflections
a = 16.9672 (9) Å	θ = 2.0–65.8°
b = 8.0833 (3) Å	µ = 0.84 mm⁻¹
c = 25.0204 (5) Å	T = 100 K
β = 116.312 (3)°	Plate, colourless
V = 3076.0 (2) Å³	0.30 × 0.10 × 0.05 mm
Z = 4

Data collection top

Xcalibur Nova κ-geometry diffractometer	2810 independent reflections
Radiation source: fine-focus sealed tube	2765 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
ω scans	θ_max = 65.8°, θ_min = 3.9°
Absorption correction: multi-scan SCALE3 ABSPACK.Oxford Diffraction program,2005.	h = −20→16
T_min = 0.765, T_max = 0.954	k = −9→9
26986 measured reflections	l = −29→29

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.089	H-atom parameters constrained
wR(F²) = 0.247	w = 1/[σ²(F_o²) + (0.1555P)² + 10.4492P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2810 reflections	Δρ_max = 0.42 e Å⁻³
506 parameters	Δρ_min = −0.41 e Å⁻³
31 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.0 (10)

Crystal data top

C₄₁H₂₆N₂O₈	V = 3076.0 (2) Å³
M_r = 674.64	Z = 4
Monoclinic, C2	Cu Kα radiation
a = 16.9672 (9) Å	µ = 0.84 mm⁻¹
b = 8.0833 (3) Å	T = 100 K
c = 25.0204 (5) Å	0.30 × 0.10 × 0.05 mm
β = 116.312 (3)°

Data collection top

Xcalibur Nova κ-geometry diffractometer	2810 independent reflections
Absorption correction: multi-scan SCALE3 ABSPACK.Oxford Diffraction program,2005.	2765 reflections with I > 2σ(I)
T_min = 0.765, T_max = 0.954	R_int = 0.048
26986 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.089	H-atom parameters constrained
wR(F²) = 0.247	w = 1/[σ²(F_o²) + (0.1555P)² + 10.4492P] where P = (F_o² + 2F_c²)/3
S = 1.03	Δρ_max = 0.42 e Å⁻³
2810 reflections	Δρ_min = −0.41 e Å⁻³
506 parameters	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
31 restraints	Absolute structure parameter: 0.0 (10)

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	0.6699 (4)	1.1290 (9)	0.3575 (3)	0.0297 (14)
C1	0.7596 (5)	0.9247 (12)	0.3403 (3)	0.0343 (18)
C2	0.8429 (5)	0.8609 (12)	0.3548 (4)	0.0383 (19)
H2	0.8929	0.9007	0.3869	0.046*
C3	0.8517 (7)	0.7275 (14)	0.3185 (4)	0.051 (3)
H3	0.9059	0.6795	0.3274	0.061*
C4	0.7797 (7)	0.6719 (11)	0.2709 (4)	0.045 (2)
H4	0.7849	0.5869	0.2476	0.054*
C5	0.6185 (7)	0.6825 (13)	0.2045 (4)	0.051 (2)
H5	0.6246	0.6006	0.1805	0.061*
C6	0.5396 (5)	0.7458 (11)	0.1913 (4)	0.0397 (19)
H6	0.4906	0.7077	0.1581	0.048*
C7	0.5291 (6)	0.8726 (13)	0.2264 (4)	0.045 (2)
H7	0.4740	0.9174	0.2172	0.054*
C8	0.6003 (5)	0.9300 (11)	0.2759 (3)	0.0330 (17)
C9	0.6867 (5)	0.8667 (10)	0.2910 (3)	0.0300 (16)
C10	0.6958 (6)	0.7340 (11)	0.2561 (3)	0.0357 (18)
C11	0.7553 (5)	1.0684 (10)	0.3743 (3)	0.0327 (17)
C12	0.5901 (5)	1.0638 (12)	0.3127 (4)	0.0370 (19)
O1	0.8175 (4)	1.1293 (10)	0.4153 (2)	0.0455 (16)
O2	0.5208 (4)	1.1129 (10)	0.3072 (3)	0.0473 (15)
C13	0.6625 (5)	1.2696 (10)	0.3908 (3)	0.0319 (17)
C14	0.6350 (7)	1.2558 (13)	0.4354 (5)	0.049 (3)
C15	0.6304 (9)	1.3994 (16)	0.4656 (5)	0.066 (4)
H15	0.6108	1.3894	0.4947	0.079*
C16	0.6541 (7)	1.5513 (12)	0.4520 (4)	0.048 (2)
H16	0.6522	1.6448	0.4731	0.057*
C17	0.6808 (7)	1.5645 (13)	0.4089 (4)	0.053 (2)
H17	0.6962	1.6673	0.3997	0.064*
C18	0.6858 (6)	1.4236 (11)	0.3769 (4)	0.0378 (19)
H18	0.7049	1.4331	0.3474	0.045*
C19	0.6096 (9)	1.0919 (16)	0.4497 (6)	0.075 (4)
O3	0.6288 (4)	0.9599 (8)	0.4391 (3)	0.0456 (16)
N10	0.3229 (5)	0.2931 (10)	0.1435 (3)	0.0391 (17)
C21	0.3891 (5)	0.4913 (10)	0.2252 (3)	0.0337 (17)
C22	0.4615 (6)	0.5475 (14)	0.2752 (4)	0.044 (2)
H22	0.5168	0.5033	0.2849	0.053*
C23	0.4551 (6)	0.6672 (15)	0.3108 (4)	0.054 (3)
H23	0.5037	0.6976	0.3456	0.065*
C24	0.3727 (6)	0.7409 (14)	0.2959 (4)	0.048 (2)
H24	0.3698	0.8301	0.3184	0.057*
C25	0.2103 (6)	0.7475 (17)	0.2302 (4)	0.054 (3)
H25	0.2017	0.8306	0.2528	0.065*
C26	0.1413 (6)	0.6886 (13)	0.1821 (4)	0.050 (2)
H26	0.0851	0.7281	0.1724	0.060*
C27	0.1497 (6)	0.5629 (15)	0.1474 (4)	0.049 (3)
H27	0.1015	0.5232	0.1140	0.059*
C28	0.2307 (5)	0.5005 (12)	0.1614 (3)	0.0358 (19)
C29	0.3062 (6)	0.5606 (13)	0.2110 (4)	0.043 (2)
C30	0.2975 (6)	0.6854 (12)	0.2471 (4)	0.044 (2)
C31	0.4000 (5)	0.3579 (12)	0.1887 (3)	0.0346 (18)
C32	0.2408 (5)	0.3601 (16)	0.1272 (4)	0.050 (3)
O10	0.4710 (4)	0.3039 (9)	0.1955 (2)	0.0443 (15)
O20	0.1765 (4)	0.2985 (12)	0.0839 (2)	0.055 (2)
C33	0.3318 (5)	0.1532 (13)	0.1098 (4)	0.042 (2)
C34	0.3655 (7)	0.1701 (12)	0.0688 (4)	0.043 (2)
C35	0.3706 (7)	0.0307 (11)	0.0381 (4)	0.046 (2)
H35	0.3972	0.0360	0.0126	0.056*
C36	0.3395 (7)	−0.1224 (15)	0.0456 (4)	0.051 (2)
H36	0.3406	−0.2138	0.0233	0.061*
C37	0.3039 (5)	−0.1346 (12)	0.0867 (4)	0.040 (2)
H37	0.2836	−0.2363	0.0928	0.048*
C38	0.3004 (5)	0.0026 (12)	0.1169 (4)	0.038 (2)
H38	0.2767	−0.0056	0.1439	0.046*
C39	0.4008 (9)	0.3321 (13)	0.0594 (5)	0.062 (3)
O30	0.3830 (5)	0.4663 (9)	0.0717 (3)	0.0529 (18)
O4	0.6042 (7)	1.1285 (13)	0.5074 (4)	0.035 (2)	0.50
O5	0.5336 (7)	1.1012 (15)	0.4615 (5)	0.042 (3)	0.50
O40	0.4232 (7)	0.3115 (12)	0.0144 (4)	0.032 (2)	0.50
O41	0.4828 (7)	0.3108 (13)	0.0573 (4)	0.031 (2)	0.50
C1R	0.5945 (8)	0.9758 (16)	0.5374 (6)	0.034 (3)	0.50
H1R	0.6257	0.9912	0.5798	0.041*	0.50
H2R	0.6178	0.8796	0.5270	0.041*	0.50
C2R	0.5004 (8)	0.9548 (18)	0.4806 (6)	0.040 (4)	0.50
H3R	0.5066	0.8626	0.4586	0.048*	0.50
C3R	0.5573 (12)	0.919 (3)	0.5469 (7)	0.061 (6)	0.50
H4R	0.5227	0.9436	0.5675	0.091*	0.50
H5R	0.6092	0.9863	0.5632	0.091*	0.50
H6R	0.5728	0.8035	0.5527	0.091*	0.50
C4R	0.4647 (9)	0.4620 (15)	0.0044 (6)	0.030 (3)	0.50
H7R	0.4320	0.5581	0.0051	0.036*	0.50
C5R	0.5312 (17)	0.459 (3)	0.0532 (8)	0.050 (8)	0.50
H8R	0.5911	0.4443	0.0823	0.060*	0.50
H9R	0.5095	0.5588	0.0629	0.060*	0.50
C6R	0.5578 (12)	0.466 (3)	0.0563 (9)	0.049 (8)	0.50
H10R	0.5895	0.3671	0.0568	0.073*	0.50
H11R	0.5550	0.4759	0.0936	0.073*	0.50
H12R	0.5888	0.5598	0.0515	0.073*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.030 (3)	0.024 (3)	0.040 (3)	0.006 (3)	0.020 (3)	−0.009 (3)
C1	0.030 (4)	0.034 (4)	0.046 (4)	0.007 (3)	0.024 (3)	0.006 (4)
C2	0.038 (4)	0.035 (4)	0.051 (4)	0.001 (4)	0.028 (4)	0.007 (4)
C3	0.067 (6)	0.053 (6)	0.045 (5)	0.015 (5)	0.036 (5)	0.017 (5)
C4	0.081 (6)	0.023 (4)	0.052 (5)	0.010 (5)	0.048 (5)	0.008 (4)
C5	0.078 (7)	0.037 (5)	0.041 (4)	0.002 (5)	0.030 (5)	−0.006 (4)
C6	0.043 (4)	0.020 (4)	0.045 (4)	−0.008 (4)	0.009 (4)	0.001 (4)
C7	0.049 (5)	0.036 (5)	0.048 (4)	0.001 (4)	0.021 (4)	0.001 (4)
C8	0.031 (4)	0.034 (4)	0.034 (3)	0.005 (3)	0.014 (3)	0.004 (4)
C9	0.040 (4)	0.024 (4)	0.034 (3)	0.008 (3)	0.024 (3)	0.002 (3)
C10	0.050 (5)	0.027 (4)	0.041 (4)	0.005 (4)	0.029 (4)	0.002 (4)
C11	0.043 (4)	0.023 (4)	0.041 (4)	0.006 (3)	0.027 (4)	−0.003 (3)
C12	0.034 (4)	0.034 (4)	0.046 (4)	−0.004 (4)	0.021 (3)	0.005 (4)
O1	0.036 (3)	0.053 (4)	0.042 (3)	0.002 (3)	0.013 (2)	−0.003 (3)
O2	0.037 (3)	0.046 (4)	0.068 (4)	0.007 (3)	0.031 (3)	0.000 (4)
C13	0.048 (4)	0.016 (4)	0.041 (4)	0.006 (3)	0.028 (4)	−0.004 (3)
C14	0.066 (6)	0.033 (5)	0.078 (7)	0.020 (5)	0.059 (6)	0.013 (5)
C15	0.102 (9)	0.067 (8)	0.049 (5)	0.035 (7)	0.050 (6)	0.001 (5)
C16	0.077 (7)	0.022 (4)	0.042 (5)	0.011 (4)	0.024 (5)	0.003 (4)
C17	0.064 (6)	0.025 (4)	0.060 (6)	0.006 (4)	0.018 (5)	0.001 (4)
C18	0.047 (5)	0.024 (4)	0.041 (4)	−0.008 (4)	0.018 (4)	0.004 (3)
C19	0.116 (10)	0.049 (7)	0.117 (10)	0.035 (7)	0.103 (9)	0.022 (7)
O3	0.058 (4)	0.029 (3)	0.066 (4)	0.003 (3)	0.042 (3)	0.006 (3)
N10	0.050 (4)	0.035 (4)	0.040 (3)	0.007 (3)	0.027 (3)	0.009 (3)
C21	0.038 (4)	0.026 (4)	0.045 (4)	−0.002 (3)	0.026 (3)	0.001 (4)
C22	0.039 (4)	0.051 (6)	0.042 (4)	0.004 (4)	0.018 (4)	0.009 (5)
C23	0.057 (5)	0.067 (7)	0.044 (4)	−0.022 (6)	0.028 (4)	−0.007 (5)
C24	0.066 (6)	0.037 (5)	0.052 (5)	0.007 (5)	0.037 (5)	0.004 (4)
C25	0.053 (6)	0.067 (7)	0.055 (5)	0.028 (6)	0.035 (5)	0.013 (5)
C26	0.050 (5)	0.046 (5)	0.072 (6)	0.028 (5)	0.043 (5)	0.023 (5)
C27	0.043 (5)	0.067 (7)	0.048 (4)	0.025 (5)	0.030 (4)	0.024 (5)
C28	0.045 (4)	0.039 (5)	0.036 (4)	0.011 (4)	0.029 (3)	0.014 (4)
C29	0.048 (5)	0.042 (5)	0.042 (4)	0.007 (4)	0.024 (4)	0.009 (4)
C30	0.068 (6)	0.033 (5)	0.038 (4)	0.008 (4)	0.031 (4)	0.013 (4)
C31	0.033 (4)	0.040 (5)	0.037 (4)	0.012 (4)	0.021 (3)	0.007 (4)
C32	0.035 (4)	0.075 (8)	0.039 (4)	0.005 (5)	0.017 (4)	0.017 (5)
O10	0.035 (3)	0.045 (4)	0.052 (3)	0.000 (3)	0.019 (2)	−0.006 (3)
O20	0.043 (3)	0.082 (6)	0.037 (3)	0.009 (4)	0.015 (3)	−0.009 (4)
C33	0.035 (4)	0.053 (6)	0.036 (4)	−0.001 (4)	0.015 (3)	0.004 (4)
C34	0.059 (6)	0.033 (5)	0.043 (5)	−0.005 (4)	0.028 (4)	−0.005 (4)
C35	0.089 (7)	0.017 (4)	0.047 (5)	−0.008 (4)	0.043 (5)	0.004 (4)
C36	0.064 (6)	0.049 (6)	0.044 (5)	−0.011 (5)	0.029 (5)	−0.002 (5)
C37	0.035 (4)	0.047 (5)	0.045 (4)	−0.007 (4)	0.024 (4)	0.002 (4)
C38	0.033 (4)	0.046 (5)	0.044 (4)	0.002 (4)	0.024 (4)	−0.001 (4)
C39	0.111 (9)	0.026 (5)	0.080 (7)	0.008 (6)	0.071 (7)	0.009 (5)
O30	0.082 (5)	0.033 (4)	0.058 (4)	0.007 (4)	0.044 (4)	−0.004 (3)
O4	0.038 (5)	0.031 (6)	0.035 (5)	−0.008 (5)	0.014 (4)	0.006 (5)
O5	0.050 (6)	0.041 (7)	0.057 (6)	−0.005 (6)	0.042 (6)	−0.023 (6)
O40	0.044 (6)	0.015 (5)	0.041 (5)	−0.008 (5)	0.023 (5)	−0.006 (5)
O41	0.039 (6)	0.027 (5)	0.037 (5)	−0.006 (5)	0.026 (5)	0.008 (5)
C1R	0.046 (9)	0.024 (8)	0.025 (6)	−0.013 (7)	0.008 (7)	0.002 (6)
C2R	0.043 (9)	0.041 (10)	0.039 (8)	−0.021 (9)	0.020 (8)	−0.021 (7)
C3R	0.041 (11)	0.052 (13)	0.094 (16)	0.029 (11)	0.034 (11)	0.019 (12)
C4R	0.030 (7)	0.019 (7)	0.058 (9)	0.001 (7)	0.035 (7)	0.002 (7)
C5R	0.024 (12)	0.090 (19)	0.030 (10)	0.004 (11)	0.006 (8)	0.016 (12)
C6R	0.039 (16)	0.064 (15)	0.036 (11)	−0.001 (10)	0.011 (10)	−0.043 (11)

Geometric parameters (Å, º) top

N1—C11	1.405 (10)	C24—H24	0.9300
N1—C12	1.421 (10)	C25—C26	1.341 (15)
N1—C13	1.448 (10)	C25—C30	1.438 (14)
C1—C9	1.385 (11)	C25—H25	0.9299
C1—C2	1.393 (11)	C26—C27	1.383 (15)
C1—C11	1.461 (11)	C26—H26	0.9299
C2—C3	1.459 (14)	C27—C28	1.356 (11)
C2—H2	0.9300	C27—H27	0.9299
C3—C4	1.350 (14)	C28—C29	1.418 (12)
C3—H3	0.9300	C28—C32	1.477 (14)
C4—C10	1.394 (13)	C29—C30	1.405 (13)
C4—H4	0.9300	C31—O10	1.219 (10)
C5—C6	1.331 (13)	C32—O20	1.251 (11)
C5—C10	1.434 (13)	C33—C38	1.372 (14)
C5—H5	0.9300	C33—C34	1.383 (13)
C6—C7	1.411 (13)	C34—C35	1.388 (13)
C6—H6	0.9300	C34—C39	1.501 (13)
C7—C8	1.373 (12)	C35—C36	1.390 (14)
C7—H7	0.9300	C35—H35	0.9301
C8—C9	1.436 (10)	C36—C37	1.408 (12)
C8—C12	1.480 (12)	C36—H36	0.9302
C9—C10	1.435 (11)	C37—C38	1.359 (13)
C11—O1	1.204 (10)	C37—H37	0.9300
C12—O2	1.190 (10)	C38—H38	0.9302
C13—C14	1.391 (12)	C39—O30	1.202 (13)
C13—C18	1.396 (12)	C39—O40	1.349 (13)
C14—C15	1.406 (15)	C39—O41	1.426 (14)
C14—C19	1.486 (16)	O4—C1R	1.492 (10)
C15—C16	1.381 (17)	O5—C2R	1.478 (10)
C15—H15	0.9300	O40—C4R	1.481 (9)
C16—C17	1.347 (14)	O41—C5R	1.484 (11)
C16—H16	0.9300	C1R—C2Rⁱ	1.476 (8)
C17—C18	1.417 (13)	C1R—H1R	0.9601
C17—H17	0.9300	C1R—H2R	0.9599
C18—H18	0.9301	C2R—C1Rⁱ	1.476 (8)
C19—O3	1.180 (14)	C2R—C3R	1.533 (11)
C19—O5	1.446 (13)	C2R—H3R	0.9599
C19—O4	1.514 (14)	C3R—H4R	0.9599
N10—C32	1.376 (11)	C3R—H5R	0.9600
N10—C31	1.397 (11)	C3R—H6R	0.9600
N10—C33	1.459 (12)	C4R—C5Rⁱⁱ	1.472 (8)
C21—C22	1.385 (12)	C4R—C6R	1.538 (11)
C21—C29	1.405 (12)	C4R—H7R	0.9601
C21—C31	1.477 (12)	C5R—C4Rⁱⁱ	1.472 (8)
C22—C23	1.351 (15)	C5R—H8R	0.9600
C22—H22	0.9300	C5R—H9R	0.9600
C23—C24	1.410 (14)	C6R—H10R	0.9599
C23—H23	0.9300	C6R—H11R	0.9603
C24—C30	1.391 (14)	C6R—H12R	0.9599

C11—N1—C12	127.0 (7)	C25—C26—C27	122.2 (8)
C11—N1—C13	116.3 (6)	C25—C26—H26	119.8
C12—N1—C13	116.7 (6)	C27—C26—H26	117.9
C9—C1—C2	120.7 (8)	C28—C27—C26	119.0 (9)
C9—C1—C11	122.1 (7)	C28—C27—H27	119.4
C2—C1—C11	116.7 (8)	C26—C27—H27	121.6
C1—C2—C3	118.9 (8)	C27—C28—C29	121.2 (9)
C1—C2—H2	122.0	C27—C28—C32	120.1 (8)
C3—C2—H2	119.2	C29—C28—C32	118.6 (7)
C4—C3—C2	119.5 (9)	C30—C29—C21	120.2 (8)
C4—C3—H3	118.9	C30—C29—C28	119.8 (8)
C2—C3—H3	121.5	C21—C29—C28	119.9 (9)
C3—C4—C10	122.1 (8)	C24—C30—C29	118.6 (9)
C3—C4—H4	119.8	C24—C30—C25	124.7 (9)
C10—C4—H4	118.0	C29—C30—C25	116.7 (9)
C6—C5—C10	122.0 (8)	O10—C31—N10	119.5 (8)
C6—C5—H5	120.0	O10—C31—C21	124.1 (8)
C10—C5—H5	118.0	N10—C31—C21	116.4 (6)
C5—C6—C7	121.1 (8)	O20—C32—N10	118.6 (10)
C5—C6—H6	119.8	O20—C32—C28	121.8 (8)
C7—C6—H6	119.2	N10—C32—C28	119.6 (8)
C8—C7—C6	120.2 (8)	C38—C33—C34	119.8 (9)
C8—C7—H7	118.5	C38—C33—N10	117.8 (7)
C6—C7—H7	121.3	C34—C33—N10	122.3 (9)
C7—C8—C9	120.3 (8)	C33—C34—C35	118.5 (9)
C7—C8—C12	120.7 (7)	C33—C34—C39	121.8 (9)
C9—C8—C12	118.9 (7)	C35—C34—C39	119.6 (8)
C1—C9—C10	120.0 (7)	C34—C35—C36	121.9 (8)
C1—C9—C8	121.3 (7)	C34—C35—H35	120.7
C10—C9—C8	118.6 (7)	C36—C35—H35	117.4
C4—C10—C5	123.6 (8)	C35—C36—C37	118.1 (10)
C4—C10—C9	118.7 (8)	C35—C36—H36	121.2
C5—C10—C9	117.5 (8)	C37—C36—H36	120.6
O1—C11—N1	120.7 (7)	C38—C37—C36	119.3 (9)
O1—C11—C1	124.8 (7)	C38—C37—H37	121.2
N1—C11—C1	114.5 (7)	C36—C37—H37	119.5
O2—C12—N1	121.1 (9)	C37—C38—C33	122.4 (7)
O2—C12—C8	123.6 (8)	C37—C38—H38	119.2
N1—C12—C8	115.3 (7)	C33—C38—H38	118.5
C14—C13—C18	120.3 (8)	O30—C39—O40	121.4 (10)
C14—C13—N1	123.0 (8)	O30—C39—O41	118.6 (11)
C18—C13—N1	116.7 (6)	O40—C39—O41	46.7 (7)
C13—C14—C15	118.9 (10)	O30—C39—C34	125.7 (9)
C13—C14—C19	120.1 (9)	O40—C39—C34	107.6 (9)
C15—C14—C19	121.0 (9)	O41—C39—C34	111.3 (9)
C16—C15—C14	120.7 (9)	C1R—O4—C19	112.7 (10)
C16—C15—H15	121.0	C19—O5—C2R	121.8 (11)
C14—C15—H15	118.4	C39—O40—C4R	111.8 (9)
C17—C16—C15	120.4 (9)	C39—O41—C5R	118.9 (13)
C17—C16—H16	119.8	C2Rⁱ—C1R—O4	106.9 (11)
C15—C16—H16	119.8	C2Rⁱ—C1R—H1R	110.2
C16—C17—C18	121.0 (9)	O4—C1R—H1R	108.6
C16—C17—H17	120.0	O4—C1R—H2R	112.5
C18—C17—H17	118.9	H1R—C1R—H2R	108.2
C13—C18—C17	118.7 (8)	C1Rⁱ—C2R—O5	109.3 (12)
C13—C18—H18	120.6	O5—C2R—H3R	106.4
C17—C18—H18	120.7	O5—C2R—C3R	110.8 (14)
O3—C19—O5	116.9 (12)	C1Rⁱ—C2R—H3R	107.2
O3—C19—C14	127.8 (8)	C3R—C2R—H3R	107.2
O5—C19—C14	112.5 (9)	C2R—C3R—H4R	107.4
O3—C19—O4	122.1 (11)	C2R—C3R—H5R	111.8
O5—C19—O4	50.3 (6)	H4R—C3R—H5R	108.3
C14—C19—O4	101.7 (10)	C2R—C3R—H6R	110.3
C32—N10—C31	123.6 (8)	C5Rⁱⁱ—C4R—O40	112.7 (14)
C32—N10—C33	119.0 (8)	O40—C4R—C6R	105.2 (14)
C31—N10—C33	117.3 (7)	C5Rⁱⁱ—C4R—C6R	110.5 (12)
C22—C21—C29	119.0 (8)	O40—C4R—H7R	109.8
C22—C21—C31	119.6 (7)	C5Rⁱⁱ—C4R—H7R	108.1
C29—C21—C31	121.4 (7)	C6R—C4R—H7R	110.7
C23—C22—C21	122.1 (9)	C4Rⁱⁱ—C5R—O41	110.3 (12)
C23—C22—H22	118.0	C4Rⁱⁱ—C5R—H8R	104.5
C21—C22—H22	119.9	O41—C5R—H8R	106.1
C22—C23—C24	119.3 (9)	C4Rⁱⁱ—C5R—H9R	115.3
C22—C23—H23	120.7	O41—C5R—H9R	112.0
C24—C23—H23	120.0	H8R—C5R—H9R	108.0
C30—C24—C23	120.8 (9)	C4R—C6R—H10R	110.7
C30—C24—H24	120.5	C4R—C6R—H11R	110.4
C23—C24—H24	118.6	H10R—C6R—H11R	109.0
C26—C25—C30	121.0 (10)	C4Rⁱⁱ—C6R—H12R	77.5
C26—C25—H25	119.6	H10R—C6R—H12R	109.0
C30—C25—H25	119.4	H11R—C6R—H12R	108.7

C9—C1—C2—C3	−2.3 (12)	C25—C26—C27—C28	−2.1 (15)
C11—C1—C2—C3	−174.4 (7)	C26—C27—C28—C29	0.6 (13)
C1—C2—C3—C4	1.9 (13)	C26—C27—C28—C32	176.6 (8)
C2—C3—C4—C10	−2.3 (13)	C22—C21—C29—C30	0.3 (13)
C10—C5—C6—C7	2.9 (14)	C31—C21—C29—C30	178.9 (8)
C5—C6—C7—C8	−1.8 (14)	C22—C21—C29—C28	−177.5 (8)
C6—C7—C8—C9	2.8 (13)	C31—C21—C29—C28	1.1 (12)
C6—C7—C8—C12	179.6 (8)	C27—C28—C29—C30	1.0 (13)
C2—C1—C9—C10	3.1 (12)	C32—C28—C29—C30	−175.1 (8)
C11—C1—C9—C10	174.7 (7)	C27—C28—C29—C21	178.8 (8)
C2—C1—C9—C8	179.3 (7)	C32—C28—C29—C21	2.7 (12)
C11—C1—C9—C8	−9.1 (12)	C23—C24—C30—C29	−3.5 (14)
C7—C8—C9—C1	179.0 (8)	C23—C24—C30—C25	176.9 (9)
C12—C8—C9—C1	2.1 (12)	C21—C29—C30—C24	1.5 (13)
C7—C8—C9—C10	−4.7 (12)	C28—C29—C30—C24	179.4 (8)
C12—C8—C9—C10	178.4 (7)	C21—C29—C30—C25	−178.9 (8)
C3—C4—C10—C5	177.4 (9)	C28—C29—C30—C25	−1.0 (13)
C3—C4—C10—C9	3.0 (12)	C26—C25—C30—C24	179.2 (10)
C6—C5—C10—C4	−179.2 (9)	C26—C25—C30—C29	−0.4 (14)
C6—C5—C10—C9	−4.8 (13)	C32—N10—C31—O10	−171.1 (8)
C1—C9—C10—C4	−3.4 (12)	C33—N10—C31—O10	4.9 (12)
C8—C9—C10—C4	−179.7 (7)	C32—N10—C31—C21	8.3 (12)
C1—C9—C10—C5	−178.1 (8)	C33—N10—C31—C21	−175.6 (7)
C8—C9—C10—C5	5.6 (11)	C22—C21—C31—O10	−8.5 (13)
C12—N1—C11—O1	−175.8 (8)	C29—C21—C31—O10	173.0 (8)
C13—N1—C11—O1	1.9 (11)	C22—C21—C31—N10	172.1 (8)
C12—N1—C11—C1	1.2 (11)	C29—C21—C31—N10	−6.5 (11)
C13—N1—C11—C1	179.0 (7)	C31—N10—C32—O20	175.9 (8)
C9—C1—C11—O1	−175.7 (8)	C33—N10—C32—O20	0.0 (13)
C2—C1—C11—O1	−3.8 (12)	C31—N10—C32—C28	−4.7 (13)
C9—C1—C11—N1	7.4 (11)	C33—N10—C32—C28	179.3 (7)
C2—C1—C11—N1	179.3 (7)	C27—C28—C32—O20	2.1 (13)
C11—N1—C12—O2	170.8 (8)	C29—C28—C32—O20	178.2 (9)
C13—N1—C12—O2	−7.0 (12)	C27—C28—C32—N10	−177.2 (8)
C11—N1—C12—C8	−7.5 (12)	C29—C28—C32—N10	−1.1 (12)
C13—N1—C12—C8	174.8 (7)	C32—N10—C33—C38	−72.0 (10)
C7—C8—C12—O2	10.6 (13)	C31—N10—C33—C38	111.8 (9)
C9—C8—C12—O2	−172.6 (8)	C32—N10—C33—C34	104.0 (10)
C7—C8—C12—N1	−171.2 (8)	C31—N10—C33—C34	−72.2 (10)
C9—C8—C12—N1	5.6 (11)	C38—C33—C34—C35	−3.2 (14)
C11—N1—C13—C14	−102.2 (10)	N10—C33—C34—C35	−179.2 (9)
C12—N1—C13—C14	75.8 (11)	C38—C33—C34—C39	−180.0 (10)
C11—N1—C13—C18	76.9 (9)	N10—C33—C34—C39	4.1 (14)
C12—N1—C13—C18	−105.1 (8)	C33—C34—C35—C36	2.8 (16)
C18—C13—C14—C15	0.5 (15)	C39—C34—C35—C36	179.6 (11)
N1—C13—C14—C15	179.6 (9)	C34—C35—C36—C37	−1.5 (17)
C18—C13—C14—C19	179.5 (10)	C35—C36—C37—C38	0.6 (14)
N1—C13—C14—C19	−1.4 (15)	C36—C37—C38—C33	−1.2 (13)
C13—C14—C15—C16	−1.0 (18)	C34—C33—C38—C37	2.5 (14)
C19—C14—C15—C16	179.9 (12)	N10—C33—C38—C37	178.6 (7)
C14—C15—C16—C17	1.1 (18)	C33—C34—C39—O30	−21.5 (19)
C15—C16—C17—C18	−0.6 (16)	C35—C34—C39—O30	161.8 (12)
C14—C13—C18—C17	0.0 (13)	C33—C34—C39—O40	−176.1 (10)
N1—C13—C18—C17	−179.2 (8)	C35—C34—C39—O40	7.3 (15)
C16—C17—C18—C13	0.1 (14)	C33—C34—C39—O41	134.4 (10)
C13—C14—C19—O3	20 (2)	C35—C34—C39—O41	−42.3 (15)
C15—C14—C19—O3	−160.6 (15)	C14—C19—O4—C1R	−170.2 (9)
C13—C14—C19—O5	−140.1 (10)	C14—C19—O5—C2R	−175.9 (11)
C15—C14—C19—O5	38.9 (17)	C34—C39—O40—C4R	−176.0 (10)
C13—C14—C19—O4	168.3 (9)	C34—C39—O41—C5R	−175.0 (11)
C15—C14—C19—O4	−12.7 (15)	C19—O4—C1R—C2Rⁱ	−96.0 (13)
C29—C21—C22—C23	−0.2 (14)	C19—O5—C2R—C1Rⁱ	−153.8 (12)
C31—C21—C22—C23	−178.9 (8)	C19—O5—C2R—C3R	77.7 (16)
C21—C22—C23—C24	−1.7 (15)	C39—O40—C4R—C5Rⁱⁱ	−165.2 (12)
C22—C23—C24—C30	3.6 (14)	C39—O40—C4R—C6R	74.4 (13)
C30—C25—C26—C27	2.0 (16)	C39—O41—C5R—C4Rⁱⁱ	−114.2 (17)

Symmetry codes: (i) −x+1, y, −z+1; (ii) −x+1, y, −z.

(2) top

Crystal data top

C₄₃H₃₀N₂O₈	Z = 1
M_r = 702.69	F(000) = 366
Triclinic, P1	D_x = 1.365 Mg m⁻³
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2897 (7) Å	Cell parameters from 4689 reflections
b = 10.0849 (7) Å	θ = 3.2–25.0°
c = 11.0897 (8) Å	µ = 0.10 mm⁻¹
α = 103.203 (6)°	T = 140 K
β = 111.486 (7)°	Plate, colourless
γ = 107.147 (6)°	0.30 × 0.20 × 0.10 mm
V = 855.11 (14) Å³

Data collection top

Kuma KM4CCD κ-geometry diffractometer	2388 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.034
Graphite monochromator	θ_max = 25.0°, θ_min = 3.2°
ω scans	h = −11→11
8911 measured reflections	k = −11→12
2994 independent reflections	l = −13→7

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.031	w = 1/[σ²(F_o²) + (0.030P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.058	(Δ/σ)_max = 0.001
S = 0.91	Δρ_max = 0.16 e Å⁻³
2994 reflections	Δρ_min = −0.18 e Å⁻³
479 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
3 restraints	Extinction coefficient: 0.038 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0 (10)

Crystal data top

C₄₃H₃₀N₂O₈	γ = 107.147 (6)°
M_r = 702.69	V = 855.11 (14) Å³
Triclinic, P1	Z = 1
a = 9.2897 (7) Å	Mo Kα radiation
b = 10.0849 (7) Å	µ = 0.10 mm⁻¹
c = 11.0897 (8) Å	T = 140 K
α = 103.203 (6)°	0.30 × 0.20 × 0.10 mm
β = 111.486 (7)°

Data collection top

Kuma KM4CCD κ-geometry diffractometer	2388 reflections with I > 2σ(I)
8911 measured reflections	R_int = 0.034
2994 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	H-atom parameters constrained
wR(F²) = 0.058	Δρ_max = 0.16 e Å⁻³
S = 0.91	Δρ_min = −0.18 e Å⁻³
2994 reflections	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
479 parameters	Absolute structure parameter: 0 (10)
3 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	−0.0406 (5)	0.5349 (4)	0.2678 (4)	0.0625 (10)
H1A	−0.1447	0.5103	0.2746	0.094*
H1B	0.0282	0.6407	0.3165	0.094*
H1C	−0.0657	0.5075	0.1713	0.094*
C2	0.0551 (4)	0.4505 (3)	0.3334 (3)	0.0387 (8)
H2	−0.0149	0.3448	0.2893	0.046*
C3	0.2221 (4)	0.4821 (3)	0.3269 (3)	0.0385 (8)
H3A	0.2911	0.5880	0.3736	0.046*
H3B	0.1986	0.4553	0.2308	0.046*
C4	0.3224 (4)	0.3995 (3)	0.3906 (3)	0.0344 (7)
H4	0.3570	0.4319	0.4890	0.041*
C5	0.4762 (4)	0.4201 (4)	0.3663 (3)	0.0483 (9)
H5A	0.5356	0.3667	0.4091	0.072*
H5B	0.4391	0.3817	0.2675	0.072*
H5C	0.5507	0.5247	0.4057	0.072*
O1	0.1007 (2)	0.5014 (2)	0.48349 (18)	0.0327 (5)
O2	−0.1456 (3)	0.3224 (3)	0.4362 (2)	0.0621 (7)
O3	0.4598 (2)	0.5489 (2)	0.8068 (2)	0.0334 (5)
O4	0.1725 (2)	0.8304 (2)	0.6826 (2)	0.0375 (5)
N1	0.3194 (3)	0.6924 (2)	0.7465 (2)	0.0230 (5)
C6	−0.0133 (4)	0.4303 (3)	0.5189 (3)	0.0342 (7)
C7	0.0365 (3)	0.4926 (3)	0.6709 (3)	0.0266 (6)
C8	0.1889 (3)	0.6094 (3)	0.7760 (3)	0.0254 (6)
C9	0.2212 (4)	0.6523 (3)	0.9143 (3)	0.0331 (7)
H9	0.3291	0.7304	0.9851	0.040*
C10	0.0998 (4)	0.5817 (3)	0.9504 (3)	0.0395 (8)
H10	0.1235	0.6138	1.0467	0.047*
C11	−0.0541 (4)	0.4672 (3)	0.8478 (3)	0.0388 (8)
H11	−0.1391	0.4185	0.8719	0.047*
C12	−0.0847 (3)	0.4229 (3)	0.7099 (3)	0.0345 (7)
H12	−0.1909	0.3430	0.6387	0.041*
C13	0.4519 (3)	0.6475 (3)	0.7612 (3)	0.0240 (6)
C14	0.5754 (3)	0.7235 (3)	0.7192 (3)	0.0209 (6)
C15	0.7074 (3)	0.6828 (3)	0.7298 (3)	0.0267 (6)
H15	0.7156	0.6038	0.7626	0.032*
C16	0.8284 (3)	0.7554 (3)	0.6932 (3)	0.0282 (7)
H16	0.9202	0.7266	0.7014	0.034*
C17	0.8155 (3)	0.8666 (3)	0.6450 (3)	0.0274 (7)
H17	0.9003	0.9164	0.6211	0.033*
C18	0.6803 (3)	0.9102 (3)	0.6291 (3)	0.0239 (6)
C19	0.6594 (3)	1.0220 (3)	0.5769 (3)	0.0292 (7)
H19	0.7399	1.0719	0.5492	0.035*
C20	0.5264 (3)	1.0593 (3)	0.5640 (3)	0.0325 (7)
H20	0.5147	1.1352	0.5273	0.039*
C21	0.4059 (3)	0.9879 (3)	0.6025 (3)	0.0292 (7)
H21	0.3123	1.0144	0.5927	0.035*
C22	0.4227 (3)	0.8791 (3)	0.6551 (3)	0.0217 (6)
C23	0.5595 (3)	0.8375 (3)	0.6690 (3)	0.0212 (6)
C24	0.2953 (3)	0.8023 (3)	0.6943 (3)	0.0270 (7)
O1A	0.2080 (2)	0.2392 (2)	0.32080 (18)	0.0325 (5)
O2A	0.2111 (3)	0.2232 (2)	0.5199 (2)	0.0509 (6)
O3A	−0.0925 (2)	0.0754 (2)	−0.0006 (2)	0.0335 (5)
O4A	0.2685 (2)	−0.1024 (2)	0.2366 (2)	0.0366 (5)
N1A	0.0849 (2)	−0.0209 (2)	0.1095 (2)	0.0221 (5)
C6A	0.1549 (3)	0.1676 (3)	0.3949 (3)	0.0312 (7)
C7A	0.0147 (3)	0.0157 (3)	0.3062 (3)	0.0260 (6)
C8A	−0.0230 (3)	−0.0719 (3)	0.1719 (3)	0.0255 (6)
C9A	−0.1613 (3)	−0.2085 (3)	0.0974 (3)	0.0301 (7)
H9A	−0.1853	−0.2668	0.0053	0.036*
C10A	−0.2673 (4)	−0.2621 (3)	0.1535 (3)	0.0360 (7)
H10A	−0.3643	−0.3569	0.1012	0.043*
C11A	−0.2299 (4)	−0.1778 (3)	0.2864 (3)	0.0377 (7)
H11A	−0.3026	−0.2132	0.3261	0.045*
C12A	−0.0897 (4)	−0.0410 (3)	0.3629 (3)	0.0353 (7)
H12A	−0.0632	0.0152	0.4564	0.042*
C13A	0.0403 (3)	0.0602 (3)	0.0263 (3)	0.0240 (6)
C14A	0.1596 (3)	0.1228 (3)	−0.0253 (3)	0.0205 (6)
C15A	0.1204 (3)	0.1984 (3)	−0.1120 (3)	0.0285 (7)
H15A	0.0160	0.2106	−0.1382	0.034*
C16A	0.2339 (4)	0.2593 (3)	−0.1619 (3)	0.0340 (7)
H16A	0.2076	0.3140	−0.2210	0.041*
C17A	0.3825 (4)	0.2427 (3)	−0.1245 (3)	0.0337 (7)
H17A	0.4565	0.2820	−0.1618	0.040*
C18A	0.4285 (3)	0.1668 (3)	−0.0353 (3)	0.0270 (7)
C19A	0.5813 (3)	0.1466 (3)	0.0062 (3)	0.0344 (7)
H19A	0.6582	0.1837	−0.0295	0.041*
C20A	0.6235 (3)	0.0770 (3)	0.0976 (3)	0.0355 (7)
H20A	0.7285	0.0658	0.1248	0.043*
C21A	0.5118 (3)	0.0198 (3)	0.1502 (3)	0.0315 (7)
H21A	0.5425	−0.0274	0.2156	0.038*
C22A	0.3585 (3)	0.0320 (3)	0.1078 (3)	0.0239 (6)
C23A	0.3138 (3)	0.1056 (3)	0.0158 (3)	0.0231 (6)
C24A	0.2395 (3)	−0.0355 (3)	0.1576 (3)	0.0261 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.073 (3)	0.070 (3)	0.054 (2)	0.045 (2)	0.023 (2)	0.033 (2)
C2	0.0461 (19)	0.0342 (18)	0.0274 (17)	0.0162 (15)	0.0115 (15)	0.0075 (14)
C3	0.051 (2)	0.0341 (18)	0.0294 (17)	0.0127 (16)	0.0225 (15)	0.0114 (14)
C4	0.0372 (17)	0.0293 (17)	0.0263 (16)	0.0044 (14)	0.0158 (14)	0.0038 (14)
C5	0.041 (2)	0.046 (2)	0.046 (2)	0.0067 (17)	0.0255 (17)	0.0051 (17)
O1	0.0341 (11)	0.0299 (11)	0.0319 (11)	0.0122 (10)	0.0145 (9)	0.0112 (9)
O2	0.0386 (14)	0.0568 (16)	0.0508 (15)	−0.0077 (13)	0.0150 (12)	−0.0006 (13)
O3	0.0299 (11)	0.0354 (12)	0.0480 (13)	0.0161 (9)	0.0235 (10)	0.0254 (10)
O4	0.0315 (12)	0.0349 (12)	0.0643 (15)	0.0201 (10)	0.0311 (11)	0.0262 (11)
N1	0.0197 (12)	0.0225 (12)	0.0321 (13)	0.0087 (10)	0.0170 (11)	0.0108 (11)
C6	0.0258 (16)	0.0327 (18)	0.0445 (19)	0.0131 (15)	0.0165 (16)	0.0141 (16)
C7	0.0203 (14)	0.0238 (15)	0.0413 (17)	0.0113 (13)	0.0175 (13)	0.0140 (14)
C8	0.0264 (16)	0.0246 (16)	0.0377 (17)	0.0126 (13)	0.0238 (14)	0.0150 (14)
C9	0.0343 (17)	0.0324 (17)	0.0379 (18)	0.0145 (14)	0.0218 (15)	0.0132 (15)
C10	0.051 (2)	0.0389 (19)	0.053 (2)	0.0247 (17)	0.0383 (18)	0.0242 (17)
C11	0.0431 (19)	0.0356 (19)	0.068 (2)	0.0221 (16)	0.0447 (18)	0.0301 (18)
C12	0.0260 (15)	0.0260 (17)	0.061 (2)	0.0145 (13)	0.0246 (15)	0.0206 (15)
C13	0.0221 (15)	0.0224 (16)	0.0271 (16)	0.0074 (13)	0.0134 (13)	0.0081 (14)
C14	0.0176 (14)	0.0212 (15)	0.0221 (14)	0.0070 (12)	0.0098 (12)	0.0059 (12)
C15	0.0222 (15)	0.0295 (17)	0.0322 (16)	0.0118 (13)	0.0151 (13)	0.0127 (14)
C16	0.0231 (15)	0.0312 (17)	0.0358 (17)	0.0139 (13)	0.0183 (14)	0.0105 (14)
C17	0.0219 (15)	0.0285 (16)	0.0310 (16)	0.0056 (13)	0.0165 (13)	0.0091 (14)
C18	0.0216 (15)	0.0226 (15)	0.0242 (15)	0.0063 (12)	0.0116 (13)	0.0058 (12)
C19	0.0286 (16)	0.0293 (17)	0.0329 (17)	0.0088 (14)	0.0184 (14)	0.0148 (14)
C20	0.0312 (17)	0.0310 (17)	0.0382 (18)	0.0125 (14)	0.0158 (14)	0.0194 (15)
C21	0.0242 (16)	0.0270 (16)	0.0376 (17)	0.0096 (13)	0.0144 (14)	0.0156 (14)
C22	0.0192 (14)	0.0190 (14)	0.0256 (15)	0.0062 (12)	0.0108 (12)	0.0079 (13)
C23	0.0179 (14)	0.0212 (15)	0.0203 (14)	0.0033 (12)	0.0103 (12)	0.0049 (12)
C24	0.0212 (15)	0.0227 (16)	0.0368 (18)	0.0081 (13)	0.0147 (14)	0.0103 (14)
O1A	0.0408 (12)	0.0293 (11)	0.0274 (11)	0.0095 (9)	0.0202 (9)	0.0101 (9)
O2A	0.0794 (16)	0.0444 (14)	0.0263 (13)	0.0200 (13)	0.0256 (12)	0.0153 (11)
O3A	0.0287 (11)	0.0485 (13)	0.0422 (12)	0.0243 (10)	0.0218 (9)	0.0290 (11)
O4A	0.0359 (12)	0.0511 (14)	0.0394 (12)	0.0272 (11)	0.0204 (10)	0.0281 (11)
N1A	0.0207 (12)	0.0296 (13)	0.0229 (12)	0.0129 (11)	0.0128 (10)	0.0136 (11)
C6A	0.0373 (18)	0.0396 (18)	0.0312 (18)	0.0245 (15)	0.0217 (15)	0.0166 (15)
C7A	0.0305 (16)	0.0330 (17)	0.0280 (15)	0.0203 (14)	0.0183 (13)	0.0172 (14)
C8A	0.0241 (15)	0.0357 (18)	0.0295 (17)	0.0175 (14)	0.0171 (13)	0.0195 (15)
C9A	0.0315 (16)	0.0314 (17)	0.0316 (16)	0.0145 (14)	0.0153 (14)	0.0162 (14)
C10A	0.0270 (16)	0.0393 (18)	0.047 (2)	0.0128 (14)	0.0191 (15)	0.0243 (17)
C11A	0.0439 (19)	0.049 (2)	0.049 (2)	0.0269 (17)	0.0357 (17)	0.0329 (17)
C12A	0.0452 (19)	0.0443 (19)	0.0385 (18)	0.0265 (16)	0.0292 (16)	0.0259 (16)
C13A	0.0260 (16)	0.0248 (16)	0.0221 (15)	0.0115 (13)	0.0114 (13)	0.0086 (13)
C14A	0.0224 (15)	0.0219 (14)	0.0205 (15)	0.0108 (12)	0.0120 (12)	0.0081 (12)
C15A	0.0304 (16)	0.0285 (17)	0.0301 (16)	0.0120 (14)	0.0166 (13)	0.0129 (14)
C16A	0.0394 (18)	0.0352 (18)	0.0382 (18)	0.0169 (15)	0.0232 (15)	0.0218 (15)
C17A	0.0375 (18)	0.0333 (17)	0.0358 (18)	0.0104 (15)	0.0252 (15)	0.0143 (15)
C18A	0.0260 (16)	0.0265 (16)	0.0276 (16)	0.0078 (13)	0.0164 (14)	0.0063 (14)
C19A	0.0268 (16)	0.0399 (18)	0.0382 (18)	0.0117 (15)	0.0216 (15)	0.0099 (15)
C20A	0.0229 (16)	0.0425 (19)	0.0416 (19)	0.0168 (14)	0.0160 (15)	0.0111 (16)
C21A	0.0269 (16)	0.0406 (19)	0.0314 (17)	0.0185 (15)	0.0138 (14)	0.0150 (15)
C22A	0.0220 (15)	0.0272 (15)	0.0220 (15)	0.0122 (13)	0.0103 (13)	0.0060 (13)
C23A	0.0208 (14)	0.0203 (15)	0.0223 (15)	0.0049 (12)	0.0104 (12)	0.0023 (12)
C24A	0.0268 (16)	0.0280 (17)	0.0222 (15)	0.0124 (14)	0.0108 (13)	0.0071 (14)

Geometric parameters (Å, º) top

C1—C2	1.516 (4)	C19—C20	1.362 (3)
C1—H1A	0.9604	C19—H19	0.9609
C1—H1B	0.9588	C20—C21	1.403 (4)
C1—H1C	0.9591	C20—H20	0.9599
C2—O1	1.476 (3)	C21—C22	1.377 (3)
C2—C3	1.521 (4)	C21—H21	0.9597
C2—H2	0.9589	C22—C23	1.420 (3)
C3—C4	1.519 (4)	C22—C24	1.476 (3)
C3—H3A	0.9589	O1A—C6A	1.340 (3)
C3—H3B	0.9592	O2A—C6A	1.205 (3)
C4—O1A	1.467 (3)	O3A—C13A	1.223 (3)
C4—C5	1.513 (4)	O4A—C24A	1.225 (3)
C4—H4	0.9588	N1A—C13A	1.399 (3)
C5—H5A	0.9591	N1A—C24A	1.404 (3)
C5—H5B	0.9587	N1A—C8A	1.454 (3)
C5—H5C	0.9590	C6A—C7A	1.486 (4)
O1—C6	1.332 (3)	C7A—C12A	1.395 (3)
O2—C6	1.211 (3)	C7A—C8A	1.399 (3)
O3—C13	1.223 (3)	C8A—C9A	1.375 (4)
O4—C24	1.224 (3)	C9A—C10A	1.392 (4)
N1—C24	1.399 (3)	C9A—H9A	0.9592
N1—C13	1.401 (3)	C10A—C11A	1.377 (4)
N1—C8	1.447 (3)	C10A—H10A	0.9583
C6—C7	1.491 (4)	C11A—C12A	1.384 (4)
C7—C8	1.389 (4)	C11A—H11A	0.9610
C7—C12	1.406 (3)	C12A—H12A	0.9591
C8—C9	1.382 (4)	C13A—C14A	1.473 (3)
C9—C10	1.389 (4)	C14A—C15A	1.372 (3)
C9—H9	0.9574	C14A—C23A	1.413 (3)
C10—C11	1.381 (4)	C15A—C16A	1.413 (3)
C10—H10	0.9592	C15A—H15A	0.9591
C11—C12	1.383 (4)	C16A—C17A	1.362 (4)
C11—H11	0.9608	C16A—H16A	0.9595
C12—H12	0.9574	C17A—C18A	1.406 (4)
C13—C14	1.468 (3)	C17A—H17A	0.9610
C14—C15	1.378 (3)	C18A—C19A	1.416 (4)
C14—C23	1.409 (3)	C18A—C23A	1.433 (3)
C15—C16	1.396 (4)	C19A—C20A	1.368 (4)
C15—H15	0.9599	C19A—H19A	0.9610
C16—C17	1.365 (4)	C20A—C21A	1.412 (4)
C16—H16	0.9598	C20A—H20A	0.9590
C17—C18	1.414 (3)	C21A—C22A	1.380 (3)
C17—H17	0.9608	C21A—H21A	0.9593
C18—C19	1.410 (4)	C22A—C23A	1.407 (3)
C18—C23	1.421 (3)	C22A—C24A	1.471 (4)

C2—C1—H1A	109.3	C19—C20—C21	121.1 (3)
C2—C1—H1B	109.5	C19—C20—H20	119.4
H1A—C1—H1B	109.4	C21—C20—H20	119.5
C2—C1—H1C	109.6	C22—C21—C20	119.6 (3)
H1A—C1—H1C	109.7	C22—C21—H21	119.8
H1B—C1—H1C	109.3	C20—C21—H21	120.7
O1—C2—C1	108.4 (2)	C21—C22—C23	120.5 (2)
O1—C2—C3	106.1 (2)	C21—C22—C24	119.9 (2)
C1—C2—C3	113.1 (3)	C23—C22—C24	119.6 (2)
O1—C2—H2	109.4	C14—C23—C22	121.0 (2)
C1—C2—H2	110.3	C14—C23—C18	119.6 (2)
C3—C2—H2	109.4	C22—C23—C18	119.4 (2)
C4—C3—C2	115.1 (2)	O4—C24—N1	119.9 (2)
C4—C3—H3A	109.2	O4—C24—C22	123.1 (3)
C2—C3—H3A	108.0	N1—C24—C22	117.0 (2)
C4—C3—H3B	108.0	C6A—O1A—C4	118.8 (2)
C2—C3—H3B	108.8	C13A—N1A—C24A	125.3 (2)
H3A—C3—H3B	107.6	C13A—N1A—C8A	117.4 (2)
O1A—C4—C5	107.3 (2)	C24A—N1A—C8A	116.3 (2)
O1A—C4—C3	106.8 (2)	O2A—C6A—O1A	123.3 (3)
C5—C4—C3	113.0 (2)	O2A—C6A—C7A	123.6 (3)
O1A—C4—H4	110.1	O1A—C6A—C7A	113.1 (2)
C5—C4—H4	110.0	C12A—C7A—C8A	118.1 (3)
C3—C4—H4	109.5	C12A—C7A—C6A	115.9 (2)
C4—C5—H5A	109.8	C8A—C7A—C6A	126.0 (2)
C4—C5—H5B	109.1	C9A—C8A—C7A	120.6 (2)
H5A—C5—H5B	109.4	C9A—C8A—N1A	118.9 (2)
C4—C5—H5C	109.6	C7A—C8A—N1A	120.5 (2)
H5A—C5—H5C	109.6	C8A—C9A—C10A	120.8 (3)
H5B—C5—H5C	109.3	C8A—C9A—H9A	119.3
C6—O1—C2	117.2 (2)	C10A—C9A—H9A	119.9
C24—N1—C13	125.2 (2)	C11A—C10A—C9A	119.1 (3)
C24—N1—C8	117.3 (2)	C11A—C10A—H10A	120.1
C13—N1—C8	117.3 (2)	C9A—C10A—H10A	120.8
O2—C6—O1	123.5 (3)	C10A—C11A—C12A	120.5 (3)
O2—C6—C7	122.0 (3)	C10A—C11A—H11A	119.9
O1—C6—C7	114.5 (2)	C12A—C11A—H11A	119.6
C8—C7—C12	117.6 (3)	C11A—C12A—C7A	120.9 (3)
C8—C7—C6	126.9 (2)	C11A—C12A—H12A	119.6
C12—C7—C6	115.5 (2)	C7A—C12A—H12A	119.5
C9—C8—C7	120.9 (2)	O3A—C13A—N1A	119.9 (2)
C9—C8—N1	117.1 (2)	O3A—C13A—C14A	123.5 (2)
C7—C8—N1	122.1 (2)	N1A—C13A—C14A	116.6 (2)
C8—C9—C10	120.5 (3)	C15A—C14A—C23A	120.6 (2)
C8—C9—H9	119.2	C15A—C14A—C13A	119.6 (2)
C10—C9—H9	120.3	C23A—C14A—C13A	119.8 (2)
C11—C10—C9	119.8 (3)	C14A—C15A—C16A	120.2 (3)
C11—C10—H10	120.7	C14A—C15A—H15A	119.8
C9—C10—H10	119.5	C16A—C15A—H15A	120.0
C10—C11—C12	119.4 (3)	C17A—C16A—C15A	120.2 (3)
C10—C11—H11	120.3	C17A—C16A—H16A	119.6
C12—C11—H11	120.3	C15A—C16A—H16A	120.2
C11—C12—C7	121.7 (3)	C16A—C17A—C18A	121.7 (3)
C11—C12—H12	119.6	C16A—C17A—H17A	119.0
C7—C12—H12	118.7	C18A—C17A—H17A	119.3
O3—C13—N1	119.7 (2)	C17A—C18A—C19A	123.7 (3)
O3—C13—C14	123.4 (2)	C17A—C18A—C23A	118.2 (2)
N1—C13—C14	116.9 (2)	C19A—C18A—C23A	118.1 (3)
C15—C14—C23	120.2 (2)	C20A—C19A—C18A	121.5 (3)
C15—C14—C13	119.4 (2)	C20A—C19A—H19A	119.0
C23—C14—C13	120.3 (2)	C18A—C19A—H19A	119.5
C14—C15—C16	120.5 (3)	C19A—C20A—C21A	120.2 (3)
C14—C15—H15	119.4	C19A—C20A—H20A	119.8
C16—C15—H15	120.0	C21A—C20A—H20A	120.0
C17—C16—C15	120.0 (3)	C22A—C21A—C20A	120.0 (3)
C17—C16—H16	120.1	C22A—C21A—H21A	119.9
C15—C16—H16	119.9	C20A—C21A—H21A	120.1
C16—C17—C18	121.7 (2)	C21A—C22A—C23A	120.8 (2)
C16—C17—H17	119.2	C21A—C22A—C24A	119.3 (2)
C18—C17—H17	119.2	C23A—C22A—C24A	119.9 (2)
C19—C18—C17	123.8 (2)	C22A—C23A—C14A	121.4 (2)
C19—C18—C23	118.3 (2)	C22A—C23A—C18A	119.4 (2)
C17—C18—C23	117.9 (2)	C14A—C23A—C18A	119.2 (2)
C20—C19—C18	121.2 (2)	O4A—C24A—N1A	119.6 (2)
C20—C19—H19	119.6	O4A—C24A—C22A	123.7 (2)
C18—C19—H19	119.2	N1A—C24A—C22A	116.7 (2)

O1—C2—C3—C4	61.6 (3)	C21—C22—C24—N1	179.7 (2)
C1—C2—C3—C4	−179.7 (3)	C23—C22—C24—N1	1.2 (3)
C2—C3—C4—O1A	55.3 (3)	C5—C4—O1A—C6A	126.6 (2)
C2—C3—C4—C5	173.2 (2)	C3—C4—O1A—C6A	−111.9 (2)
C1—C2—O1—C6	87.8 (3)	C4—O1A—C6A—O2A	−8.8 (4)
C3—C2—O1—C6	−150.4 (2)	C4—O1A—C6A—C7A	168.6 (2)
C2—O1—C6—O2	4.4 (4)	O2A—C6A—C7A—C12A	21.3 (4)
C2—O1—C6—C7	−176.8 (2)	O1A—C6A—C7A—C12A	−156.1 (2)
O2—C6—C7—C8	175.8 (3)	O2A—C6A—C7A—C8A	−160.2 (3)
O1—C6—C7—C8	−3.1 (4)	O1A—C6A—C7A—C8A	22.5 (3)
O2—C6—C7—C12	−3.5 (4)	C12A—C7A—C8A—C9A	1.4 (4)
O1—C6—C7—C12	177.6 (2)	C6A—C7A—C8A—C9A	−177.1 (2)
C12—C7—C8—C9	1.8 (4)	C12A—C7A—C8A—N1A	−177.8 (2)
C6—C7—C8—C9	−177.5 (3)	C6A—C7A—C8A—N1A	3.7 (4)
C12—C7—C8—N1	−177.5 (2)	C13A—N1A—C8A—C9A	88.4 (3)
C6—C7—C8—N1	3.2 (4)	C24A—N1A—C8A—C9A	−102.1 (3)
C24—N1—C8—C9	−100.7 (3)	C13A—N1A—C8A—C7A	−92.4 (3)
C13—N1—C8—C9	84.7 (3)	C24A—N1A—C8A—C7A	77.1 (3)
C24—N1—C8—C7	78.7 (3)	C7A—C8A—C9A—C10A	0.4 (4)
C13—N1—C8—C7	−96.0 (3)	N1A—C8A—C9A—C10A	179.6 (2)
C7—C8—C9—C10	−1.7 (4)	C8A—C9A—C10A—C11A	−1.3 (4)
N1—C8—C9—C10	177.6 (2)	C9A—C10A—C11A—C12A	0.5 (4)
C8—C9—C10—C11	0.4 (4)	C10A—C11A—C12A—C7A	1.3 (4)
C9—C10—C11—C12	0.7 (4)	C8A—C7A—C12A—C11A	−2.3 (4)
C10—C11—C12—C7	−0.6 (4)	C6A—C7A—C12A—C11A	176.4 (2)
C8—C7—C12—C11	−0.6 (4)	C24A—N1A—C13A—O3A	−174.3 (2)
C6—C7—C12—C11	178.7 (2)	C8A—N1A—C13A—O3A	−5.8 (4)
C24—N1—C13—O3	−179.2 (2)	C24A—N1A—C13A—C14A	6.1 (3)
C8—N1—C13—O3	−5.0 (3)	C8A—N1A—C13A—C14A	174.6 (2)
C24—N1—C13—C14	0.6 (3)	O3A—C13A—C14A—C15A	−2.2 (4)
C8—N1—C13—C14	174.8 (2)	N1A—C13A—C14A—C15A	177.4 (2)
O3—C13—C14—C15	0.6 (4)	O3A—C13A—C14A—C23A	177.3 (2)
N1—C13—C14—C15	−179.2 (2)	N1A—C13A—C14A—C23A	−3.1 (3)
O3—C13—C14—C23	−179.3 (2)	C23A—C14A—C15A—C16A	0.4 (4)
N1—C13—C14—C23	0.9 (3)	C13A—C14A—C15A—C16A	179.8 (2)
C23—C14—C15—C16	1.1 (4)	C14A—C15A—C16A—C17A	0.3 (4)
C13—C14—C15—C16	−178.7 (3)	C15A—C16A—C17A—C18A	−0.6 (4)
C14—C15—C16—C17	−0.8 (4)	C16A—C17A—C18A—C19A	179.9 (3)
C15—C16—C17—C18	−0.7 (4)	C16A—C17A—C18A—C23A	0.3 (4)
C16—C17—C18—C19	−178.6 (3)	C17A—C18A—C19A—C20A	177.4 (3)
C16—C17—C18—C23	1.8 (4)	C23A—C18A—C19A—C20A	−3.0 (4)
C17—C18—C19—C20	−180.0 (3)	C18A—C19A—C20A—C21A	1.6 (4)
C23—C18—C19—C20	−0.4 (4)	C19A—C20A—C21A—C22A	1.0 (4)
C18—C19—C20—C21	0.1 (4)	C20A—C21A—C22A—C23A	−2.1 (4)
C19—C20—C21—C22	0.4 (4)	C20A—C21A—C22A—C24A	176.7 (3)
C20—C21—C22—C23	−0.8 (4)	C21A—C22A—C23A—C14A	−178.2 (2)
C20—C21—C22—C24	−179.3 (3)	C24A—C22A—C23A—C14A	3.1 (3)
C15—C14—C23—C22	178.9 (2)	C21A—C22A—C23A—C18A	0.7 (3)
C13—C14—C23—C22	−1.3 (3)	C24A—C22A—C23A—C18A	−178.1 (2)
C15—C14—C23—C18	0.0 (3)	C15A—C14A—C23A—C22A	178.2 (2)
C13—C14—C23—C18	179.9 (2)	C13A—C14A—C23A—C22A	−1.2 (3)
C21—C22—C23—C14	−178.3 (3)	C15A—C14A—C23A—C18A	−0.7 (3)
C24—C22—C23—C14	0.2 (3)	C13A—C14A—C23A—C18A	179.9 (2)
C21—C22—C23—C18	0.6 (3)	C17A—C18A—C23A—C22A	−178.6 (2)
C24—C22—C23—C18	179.1 (3)	C19A—C18A—C23A—C22A	1.8 (3)
C19—C18—C23—C14	178.9 (2)	C17A—C18A—C23A—C14A	0.3 (4)
C17—C18—C23—C14	−1.4 (3)	C19A—C18A—C23A—C14A	−179.3 (2)
C19—C18—C23—C22	0.0 (3)	C13A—N1A—C24A—O4A	175.9 (2)
C17—C18—C23—C22	179.7 (2)	C8A—N1A—C24A—O4A	7.3 (3)
C13—N1—C24—O4	178.1 (2)	C13A—N1A—C24A—C22A	−4.3 (3)
C8—N1—C24—O4	3.9 (4)	C8A—N1A—C24A—C22A	−172.9 (2)
C13—N1—C24—C22	−1.6 (4)	C21A—C22A—C24A—O4A	0.5 (4)
C8—N1—C24—C22	−175.8 (2)	C23A—C22A—C24A—O4A	179.3 (3)
C21—C22—C24—O4	0.0 (4)	C21A—C22A—C24A—N1A	−179.2 (2)
C23—C22—C24—O4	−178.5 (2)	C23A—C22A—C24A—N1A	−0.5 (3)

(3) top

Crystal data top

C₄₄H₃₀N₂O₈	D_x = 1.355 Mg m⁻³
M_r = 714.70	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P3₂21	Cell parameters from 3787 reflections
Hall symbol: P 32 2"	θ = 3.4–25.0°
a = 11.873 (2) Å	µ = 0.09 mm⁻¹
c = 43.046 (9) Å	T = 140 K
V = 5255.1 (17) Å³	Plate, colourless
Z = 6	0.5 × 0.2 × 0.2 mm
F(000) = 2232

Data collection top

Kuma KM4CCD κ-geometry diffractometer	2230 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.081
Graphite monochromator	θ_max = 25.0°, θ_min = 3.7°
ω scans	h = −14→13
15932 measured reflections	k = −14→14
3556 independent reflections	l = −21→51

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.126	w = 1/[σ²(F_o²) + (0.0564P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max < 0.001
3556 reflections	Δρ_max = 0.25 e Å⁻³
487 parameters	Δρ_min = −0.28 e Å⁻³
0 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0 (10)

Crystal data top

C₄₄H₃₀N₂O₈	Z = 6
M_r = 714.70	Mo Kα radiation
Trigonal, P3₂21	µ = 0.09 mm⁻¹
a = 11.873 (2) Å	T = 140 K
c = 43.046 (9) Å	0.5 × 0.2 × 0.2 mm
V = 5255.1 (17) Å³

Data collection top

Kuma KM4CCD κ-geometry diffractometer	2230 reflections with I > 2σ(I)
15932 measured reflections	R_int = 0.081
3556 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.126	Δρ_max = 0.25 e Å⁻³
S = 0.97	Δρ_min = −0.28 e Å⁻³
3556 reflections	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
487 parameters	Absolute structure parameter: 0 (10)
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.6641 (6)	0.8586 (5)	0.04305 (10)	0.0336 (15)
H1	0.6353	0.8666	0.0633	0.040*
C2	0.7269 (6)	0.9888 (6)	0.02725 (10)	0.0389 (16)
H2	0.7645	0.9834	0.0079	0.047*
C3	0.6326 (6)	1.0358 (6)	0.02186 (11)	0.0477 (18)
H3A	0.6758	1.1154	0.0102	0.057*
H3B	0.6078	1.0545	0.0416	0.057*
C4	0.5125 (6)	0.9383 (6)	0.00435 (11)	0.0470 (16)
H4A	0.5356	0.9295	−0.0165	0.056*
H4B	0.4524	0.9700	0.0033	0.056*
C5	0.4489 (6)	0.8042 (6)	0.02100 (11)	0.0482 (17)
H5A	0.3776	0.7417	0.0087	0.058*
H5B	0.4163	0.8095	0.0410	0.058*
C6	0.5470 (6)	0.7598 (6)	0.02459 (10)	0.0391 (16)
H6A	0.5100	0.6767	0.0347	0.047*
H6B	0.5769	0.7521	0.0044	0.047*
O1	0.8294 (4)	1.0757 (4)	0.04858 (6)	0.0377 (10)
O2	0.9546 (5)	1.2025 (4)	0.00976 (7)	0.0675 (15)
C7	0.9337 (6)	1.1784 (6)	0.03725 (11)	0.0445 (16)
C8	1.0274 (6)	1.2639 (5)	0.06186 (10)	0.0365 (15)
C9	1.0051 (5)	1.2496 (5)	0.09397 (10)	0.0308 (14)
C10	1.0988 (6)	1.3305 (6)	0.11438 (11)	0.0396 (15)
H10	1.0824	1.3190	0.1363	0.047*
C11	1.2147 (7)	1.4303 (6)	0.10371 (12)	0.0494 (17)
H11	1.2807	1.4856	0.1182	0.059*
C12	1.2389 (7)	1.4466 (6)	0.07228 (12)	0.060 (2)
H12	1.3193	1.5171	0.0647	0.072*
C13	1.1466 (7)	1.3658 (7)	0.05183 (12)	0.0529 (19)
H13	1.1638	1.3764	0.0299	0.063*
N1	0.8809 (4)	1.1489 (4)	0.10678 (8)	0.0292 (11)
O3	0.9723 (4)	1.0280 (4)	0.12013 (7)	0.0443 (11)
O4	0.7881 (4)	1.2687 (4)	0.09261 (8)	0.0484 (11)
C14	0.8739 (6)	1.0379 (5)	0.11902 (10)	0.0293 (13)
C15	0.7450 (6)	0.9345 (5)	0.13048 (9)	0.0271 (13)
C16	0.7335 (6)	0.8247 (6)	0.14349 (10)	0.0363 (15)
H16	0.8094	0.8159	0.1452	0.044*
C17	0.6118 (5)	0.7248 (5)	0.15376 (9)	0.0311 (14)
H17	0.6047	0.6478	0.1629	0.037*
C18	0.5039 (6)	0.7383 (6)	0.15106 (9)	0.0342 (14)
H18	0.4218	0.6705	0.1588	0.041*
C19	0.5117 (6)	0.8475 (6)	0.13721 (10)	0.0350 (15)
C20	0.4040 (7)	0.8635 (8)	0.13282 (12)	0.0590 (19)
H20	0.3198	0.7965	0.1395	0.071*
C21	0.4155 (7)	0.9737 (7)	0.11926 (14)	0.062 (2)
H21	0.3409	0.9839	0.1163	0.075*
C22	0.5381 (7)	1.0726 (7)	0.10996 (12)	0.059 (2)
H22	0.5468	1.1486	0.0999	0.070*
C23	0.6469 (6)	1.0611 (6)	0.11384 (10)	0.0342 (14)
C24	0.6372 (5)	0.9507 (5)	0.12730 (9)	0.0259 (13)
C25	0.7732 (6)	1.1682 (6)	0.10367 (10)	0.0355 (15)
O1A	0.7648 (4)	0.8229 (3)	0.04588 (6)	0.0339 (10)
O2A	0.6422 (4)	0.6745 (4)	0.08199 (6)	0.0372 (10)
C7A	0.7423 (6)	0.7301 (5)	0.06731 (10)	0.0355 (15)
C8A	0.8569 (6)	0.7115 (5)	0.07104 (10)	0.0292 (13)
C9A	0.8422 (5)	0.5985 (6)	0.08437 (9)	0.0310 (14)
C10A	0.9471 (6)	0.5794 (5)	0.08790 (10)	0.0339 (14)
H10A	0.9341	0.5002	0.0972	0.041*
C11A	1.0698 (6)	0.6753 (6)	0.07823 (10)	0.0420 (15)
H11A	1.1438	0.6642	0.0812	0.050*
C12A	1.0837 (6)	0.7867 (6)	0.06458 (11)	0.0467 (17)
H12A	1.1676	0.8510	0.0570	0.056*
C13A	0.9809 (6)	0.8061 (6)	0.06113 (10)	0.0379 (15)
H13A	0.9928	0.8847	0.0518	0.045*
N1A	0.7157 (4)	0.4943 (4)	0.09268 (7)	0.0313 (12)
O3A	0.6819 (4)	0.4419 (4)	0.04152 (6)	0.0542 (13)
O4A	0.7490 (4)	0.5495 (4)	0.14375 (6)	0.0334 (10)
C14A	0.6346 (6)	0.4202 (6)	0.06777 (10)	0.0422 (17)
C15A	0.5001 (6)	0.3241 (5)	0.07459 (9)	0.0336 (14)
C16A	0.4203 (6)	0.2448 (6)	0.05116 (10)	0.0404 (16)
H16A	0.4546	0.2543	0.0305	0.048*
C17A	0.2921 (6)	0.1517 (7)	0.05718 (11)	0.0522 (19)
H17A	0.2380	0.0981	0.0405	0.063*
C18A	0.2423 (6)	0.1363 (6)	0.08672 (10)	0.0424 (16)
H18A	0.1539	0.0711	0.0909	0.051*
C19A	0.3231 (6)	0.2155 (5)	0.11152 (10)	0.0328 (14)
C20A	0.2740 (6)	0.2020 (6)	0.14247 (9)	0.0379 (15)
H20A	0.1848	0.1398	0.1469	0.046*
C21A	0.3556 (6)	0.2795 (6)	0.16542 (10)	0.0367 (15)
H21A	0.3247	0.2697	0.1864	0.044*
C22A	0.4855 (6)	0.3717 (5)	0.15929 (9)	0.0343 (14)
H22A	0.5399	0.4268	0.1757	0.041*
C23A	0.5362 (5)	0.3880 (5)	0.12975 (9)	0.0260 (12)
C24A	0.4524 (5)	0.3102 (5)	0.10523 (9)	0.0260 (12)
C25A	0.6727 (6)	0.4826 (5)	0.12368 (9)	0.0317 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.036 (4)	0.031 (4)	0.028 (2)	0.012 (3)	−0.002 (2)	0.001 (2)
C2	0.052 (4)	0.031 (4)	0.030 (2)	0.018 (3)	−0.006 (3)	0.000 (2)
C3	0.066 (5)	0.044 (4)	0.045 (3)	0.036 (4)	−0.008 (3)	0.004 (3)
C4	0.043 (4)	0.047 (4)	0.051 (3)	0.022 (4)	−0.011 (3)	0.001 (3)
C5	0.043 (4)	0.051 (5)	0.043 (3)	0.018 (4)	−0.006 (3)	−0.006 (3)
C6	0.041 (4)	0.034 (4)	0.029 (2)	0.009 (3)	−0.006 (2)	−0.001 (2)
O1	0.041 (3)	0.020 (2)	0.0296 (15)	−0.001 (2)	−0.0022 (17)	0.0014 (16)
O2	0.069 (4)	0.070 (4)	0.0327 (18)	0.012 (3)	0.0076 (19)	0.0109 (19)
C7	0.045 (4)	0.046 (4)	0.040 (3)	0.022 (4)	0.001 (3)	0.002 (3)
C8	0.041 (4)	0.016 (3)	0.041 (3)	0.005 (3)	0.005 (3)	0.005 (2)
C9	0.032 (4)	0.010 (3)	0.038 (2)	0.001 (3)	−0.004 (2)	−0.001 (2)
C10	0.036 (4)	0.037 (4)	0.045 (3)	0.019 (4)	−0.003 (3)	0.001 (3)
C11	0.050 (5)	0.021 (4)	0.064 (3)	0.008 (4)	−0.005 (3)	0.000 (3)
C12	0.053 (5)	0.031 (4)	0.065 (4)	−0.003 (4)	0.002 (3)	0.008 (3)
C13	0.044 (5)	0.055 (5)	0.050 (3)	0.018 (4)	0.011 (3)	0.012 (3)
N1	0.024 (3)	0.022 (3)	0.0299 (19)	0.003 (2)	−0.0022 (19)	0.0013 (19)
O3	0.032 (3)	0.036 (3)	0.059 (2)	0.013 (2)	−0.0016 (19)	0.0121 (19)
O4	0.052 (3)	0.030 (3)	0.068 (2)	0.025 (2)	0.003 (2)	0.008 (2)
C14	0.032 (4)	0.028 (4)	0.032 (2)	0.018 (3)	−0.007 (2)	0.000 (2)
C15	0.033 (4)	0.022 (3)	0.024 (2)	0.012 (3)	−0.005 (2)	−0.006 (2)
C16	0.034 (4)	0.039 (4)	0.036 (2)	0.019 (3)	−0.005 (3)	−0.003 (3)
C17	0.029 (4)	0.021 (3)	0.035 (2)	0.007 (3)	0.003 (2)	0.004 (2)
C18	0.027 (4)	0.031 (4)	0.033 (2)	0.006 (3)	0.006 (2)	−0.001 (2)
C19	0.027 (4)	0.037 (4)	0.038 (3)	0.014 (3)	0.001 (2)	−0.005 (3)
C20	0.036 (4)	0.072 (6)	0.076 (4)	0.033 (4)	0.022 (3)	0.017 (4)
C21	0.042 (5)	0.049 (5)	0.110 (5)	0.033 (4)	0.021 (4)	0.021 (4)
C22	0.054 (5)	0.074 (6)	0.073 (4)	0.051 (5)	0.019 (4)	0.021 (4)
C23	0.035 (4)	0.037 (4)	0.035 (2)	0.022 (3)	0.003 (3)	−0.003 (3)
C24	0.029 (4)	0.022 (3)	0.024 (2)	0.011 (3)	0.001 (2)	−0.004 (2)
C25	0.044 (4)	0.028 (4)	0.035 (3)	0.019 (4)	−0.005 (3)	−0.007 (3)
O1A	0.041 (3)	0.027 (2)	0.0307 (16)	0.015 (2)	−0.0036 (16)	0.0053 (15)
O2A	0.038 (3)	0.032 (3)	0.0386 (17)	0.015 (2)	0.0066 (17)	0.0082 (17)
C7A	0.045 (4)	0.025 (4)	0.023 (2)	0.008 (3)	−0.009 (3)	−0.008 (2)
C8A	0.032 (4)	0.020 (3)	0.029 (2)	0.009 (3)	−0.004 (2)	−0.002 (2)
C9A	0.024 (4)	0.031 (4)	0.029 (2)	0.007 (3)	−0.002 (2)	−0.001 (2)
C10A	0.028 (4)	0.022 (3)	0.040 (3)	0.003 (3)	−0.001 (3)	0.004 (2)
C11A	0.043 (4)	0.029 (4)	0.054 (3)	0.018 (4)	−0.006 (3)	−0.003 (3)
C12A	0.038 (4)	0.031 (4)	0.050 (3)	0.002 (3)	−0.003 (3)	0.000 (3)
C13A	0.040 (4)	0.028 (4)	0.037 (3)	0.010 (3)	−0.002 (3)	0.001 (3)
N1A	0.031 (3)	0.023 (3)	0.0261 (18)	0.004 (2)	−0.0023 (19)	0.0026 (18)
O3A	0.046 (3)	0.053 (3)	0.0268 (16)	−0.003 (2)	0.0008 (18)	0.0017 (17)
O4A	0.034 (2)	0.028 (2)	0.0322 (16)	0.011 (2)	−0.0098 (16)	−0.0054 (16)
C14A	0.044 (4)	0.035 (4)	0.031 (3)	0.008 (3)	−0.006 (3)	−0.002 (2)
C15A	0.031 (4)	0.030 (4)	0.027 (2)	0.006 (3)	−0.001 (2)	0.003 (2)
C16A	0.036 (4)	0.043 (4)	0.025 (2)	0.006 (3)	−0.002 (2)	−0.001 (2)
C17A	0.040 (4)	0.051 (5)	0.041 (3)	0.005 (4)	−0.013 (3)	−0.006 (3)
C18A	0.023 (4)	0.036 (4)	0.045 (3)	−0.002 (3)	−0.008 (3)	−0.003 (3)
C19A	0.033 (4)	0.027 (4)	0.039 (2)	0.015 (3)	−0.003 (3)	0.003 (2)
C20A	0.034 (4)	0.042 (4)	0.041 (3)	0.021 (3)	0.003 (3)	0.004 (3)
C21A	0.039 (4)	0.038 (4)	0.032 (2)	0.018 (3)	0.002 (3)	0.000 (3)
C22A	0.043 (4)	0.033 (4)	0.032 (2)	0.023 (3)	−0.004 (3)	0.001 (2)
C23A	0.031 (4)	0.023 (3)	0.031 (2)	0.018 (3)	−0.002 (2)	0.003 (2)
C24A	0.024 (3)	0.025 (3)	0.030 (2)	0.013 (3)	−0.005 (2)	−0.001 (2)
C25A	0.044 (4)	0.028 (4)	0.027 (2)	0.021 (3)	−0.001 (3)	0.002 (2)

Geometric parameters (Å, º) top

C1—O1A	1.460 (6)	C19—C24	1.441 (7)
C1—C2	1.502 (7)	C20—C21	1.375 (8)
C1—C6	1.520 (7)	C20—H20	0.9599
C1—H1	0.9599	C21—C22	1.396 (9)
C2—O1	1.460 (6)	C21—H21	0.9600
C2—C3	1.498 (8)	C22—C23	1.375 (8)
C2—H2	0.9599	C22—H22	0.9599
C3—C4	1.514 (8)	C23—C24	1.384 (7)
C3—H3A	0.9600	C23—C25	1.466 (8)
C3—H3B	0.9599	O1A—C7A	1.357 (6)
C4—C5	1.554 (8)	O2A—C7A	1.209 (6)
C4—H4A	0.9602	C7A—C8A	1.493 (8)
C4—H4B	0.9600	C8A—C9A	1.388 (7)
C5—C6	1.507 (8)	C8A—C13A	1.399 (7)
C5—H5A	0.9599	C9A—C10A	1.382 (7)
C5—H5B	0.9599	C9A—N1A	1.434 (7)
C6—H6A	0.9600	C10A—C11A	1.390 (8)
C6—H6B	0.9599	C10A—H10A	0.9599
O1—C7	1.323 (7)	C11A—C12A	1.379 (8)
O2—C7	1.214 (5)	C11A—H11A	0.9602
C7—C8	1.504 (8)	C12A—C13A	1.358 (8)
C8—C13	1.393 (8)	C12A—H12A	0.9601
C8—C9	1.401 (6)	C13A—H13A	0.9601
C9—C10	1.365 (7)	N1A—C25A	1.411 (5)
C9—N1	1.464 (6)	N1A—C14A	1.415 (6)
C10—C11	1.370 (8)	O3A—C14A	1.230 (5)
C10—H10	0.9598	O4A—C25A	1.215 (6)
C11—C12	1.376 (7)	C14A—C15A	1.455 (8)
C11—H11	0.9600	C15A—C16A	1.382 (7)
C12—C13	1.358 (8)	C15A—C24A	1.412 (6)
C12—H12	0.9599	C16A—C17A	1.387 (8)
C13—H13	0.9601	C16A—H16A	0.9598
N1—C14	1.382 (6)	C17A—C18A	1.375 (7)
N1—C25	1.414 (7)	C17A—H17A	0.9601
O3—C14	1.232 (6)	C18A—C19A	1.428 (7)
O4—C25	1.213 (6)	C18A—H18A	0.9599
C14—C15	1.488 (8)	C19A—C24A	1.403 (7)
C15—C16	1.362 (7)	C19A—C20A	1.430 (6)
C15—C24	1.393 (7)	C20A—C21A	1.367 (7)
C16—C17	1.406 (7)	C20A—H20A	0.9599
C16—H16	0.9600	C21A—C22A	1.400 (8)
C17—C18	1.373 (7)	C21A—H21A	0.9599
C17—H17	0.9599	C22A—C23A	1.378 (6)
C18—C19	1.388 (8)	C22A—H22A	0.9600
C18—H18	0.9600	C23A—C24A	1.427 (6)
C19—C20	1.397 (8)	C23A—C25A	1.462 (7)

O1A—C1—C2	106.2 (5)	C21—C20—C19	121.6 (7)
O1A—C1—C6	112.7 (5)	C21—C20—H20	118.9
C2—C1—C6	110.5 (4)	C19—C20—H20	119.5
O1A—C1—H1	109.7	C20—C21—C22	119.2 (6)
C2—C1—H1	109.2	C20—C21—H21	121.1
C6—C1—H1	108.6	C22—C21—H21	119.7
O1—C2—C3	110.4 (5)	C23—C22—C21	121.2 (6)
O1—C2—C1	104.6 (4)	C23—C22—H22	118.9
C3—C2—C1	112.0 (5)	C21—C22—H22	119.8
O1—C2—H2	109.9	C22—C23—C24	120.4 (6)
C3—C2—H2	110.4	C22—C23—C25	118.8 (6)
C1—C2—H2	109.4	C24—C23—C25	120.8 (5)
C2—C3—C4	112.7 (5)	C23—C24—C15	121.6 (5)
C2—C3—H3A	108.5	C23—C24—C19	119.4 (5)
C4—C3—H3A	109.2	C15—C24—C19	118.9 (5)
C2—C3—H3B	108.9	O4—C25—N1	119.8 (6)
C4—C3—H3B	109.6	O4—C25—C23	123.6 (6)
H3A—C3—H3B	107.9	N1—C25—C23	116.6 (5)
C3—C4—C5	110.1 (4)	C7A—O1A—C1	115.8 (4)
C3—C4—H4A	109.7	O2A—C7A—O1A	122.6 (6)
C5—C4—H4A	109.8	O2A—C7A—C8A	125.7 (5)
C3—C4—H4B	108.9	O1A—C7A—C8A	111.7 (5)
C5—C4—H4B	110.3	C9A—C8A—C13A	118.4 (6)
H4A—C4—H4B	108.0	C9A—C8A—C7A	120.3 (5)
C6—C5—C4	110.0 (5)	C13A—C8A—C7A	121.4 (5)
C6—C5—H5A	108.9	C10A—C9A—C8A	121.1 (5)
C4—C5—H5A	109.0	C10A—C9A—N1A	118.2 (5)
C6—C5—H5B	109.8	C8A—C9A—N1A	120.6 (5)
C4—C5—H5B	110.6	C9A—C10A—C11A	119.6 (6)
H5A—C5—H5B	108.6	C9A—C10A—H10A	119.3
C5—C6—C1	110.6 (5)	C11A—C10A—H10A	121.1
C5—C6—H6A	111.7	C12A—C11A—C10A	119.1 (6)
C1—C6—H6A	109.2	C12A—C11A—H11A	120.6
C5—C6—H6B	109.1	C10A—C11A—H11A	120.2
C1—C6—H6B	107.9	C13A—C12A—C11A	121.5 (6)
H6A—C6—H6B	108.2	C13A—C12A—H12A	119.4
C7—O1—C2	119.0 (4)	C11A—C12A—H12A	119.1
O2—C7—O1	124.3 (5)	C12A—C13A—C8A	120.3 (6)
O2—C7—C8	122.2 (6)	C12A—C13A—H13A	120.2
O1—C7—C8	113.5 (4)	C8A—C13A—H13A	119.5
C13—C8—C9	117.3 (5)	C25A—N1A—C14A	123.8 (5)
C13—C8—C7	117.1 (4)	C25A—N1A—C9A	119.5 (4)
C9—C8—C7	125.6 (5)	C14A—N1A—C9A	116.1 (4)
C10—C9—C8	120.8 (5)	O3A—C14A—N1A	117.9 (5)
C10—C9—N1	117.8 (4)	O3A—C14A—C15A	123.8 (5)
C8—C9—N1	121.5 (4)	N1A—C14A—C15A	118.2 (4)
C9—C10—C11	120.4 (5)	C16A—C15A—C24A	120.3 (5)
C9—C10—H10	119.8	C16A—C15A—C14A	119.8 (4)
C11—C10—H10	119.8	C24A—C15A—C14A	119.9 (4)
C10—C11—C12	120.0 (6)	C15A—C16A—C17A	120.8 (5)
C10—C11—H11	119.7	C15A—C16A—H16A	119.3
C12—C11—H11	120.2	C17A—C16A—H16A	119.9
C13—C12—C11	120.0 (6)	C18A—C17A—C16A	120.4 (5)
C13—C12—H12	119.6	C18A—C17A—H17A	120.1
C11—C12—H12	120.3	C16A—C17A—H17A	119.5
C12—C13—C8	121.5 (5)	C17A—C18A—C19A	120.1 (5)
C12—C13—H13	120.1	C17A—C18A—H18A	120.3
C8—C13—H13	118.4	C19A—C18A—H18A	119.6
C14—N1—C25	124.2 (5)	C24A—C19A—C18A	119.2 (4)
C14—N1—C9	118.5 (5)	C24A—C19A—C20A	119.4 (5)
C25—N1—C9	117.1 (5)	C18A—C19A—C20A	121.4 (5)
O3—C14—N1	119.8 (5)	C21A—C20A—C19A	119.1 (5)
O3—C14—C15	122.7 (5)	C21A—C20A—H20A	120.8
N1—C14—C15	117.4 (5)	C19A—C20A—H20A	120.1
C16—C15—C24	120.9 (5)	C20A—C21A—C22A	121.5 (4)
C16—C15—C14	119.7 (5)	C20A—C21A—H21A	120.0
C24—C15—C14	119.3 (5)	C22A—C21A—H21A	118.4
C15—C16—C17	120.3 (6)	C23A—C22A—C21A	121.1 (5)
C15—C16—H16	119.1	C23A—C22A—H22A	119.1
C17—C16—H16	120.5	C21A—C22A—H22A	119.8
C18—C17—C16	120.1 (5)	C22A—C23A—C24A	118.5 (5)
C18—C17—H17	120.2	C22A—C23A—C25A	120.7 (4)
C16—C17—H17	119.7	C24A—C23A—C25A	120.8 (4)
C17—C18—C19	121.0 (5)	C19A—C24A—C15A	119.2 (4)
C17—C18—H18	119.2	C19A—C24A—C23A	120.3 (4)
C19—C18—H18	119.8	C15A—C24A—C23A	120.4 (5)
C18—C19—C20	123.2 (6)	O4A—C25A—N1A	119.6 (5)
C18—C19—C24	118.7 (5)	O4A—C25A—C23A	123.5 (4)
C20—C19—C24	118.1 (6)	N1A—C25A—C23A	116.9 (4)

O1A—C1—C2—O1	−62.3 (5)	C9—N1—C25—C23	174.3 (4)
C6—C1—C2—O1	175.2 (4)	C22—C23—C25—O4	1.9 (7)
O1A—C1—C2—C3	178.1 (4)	C24—C23—C25—O4	−177.7 (5)
C6—C1—C2—C3	55.7 (6)	C22—C23—C25—N1	−177.0 (5)
O1—C2—C3—C4	−170.3 (4)	C24—C23—C25—N1	3.4 (6)
C1—C2—C3—C4	−54.2 (6)	C2—C1—O1A—C7A	160.9 (4)
C2—C3—C4—C5	53.5 (6)	C6—C1—O1A—C7A	−78.1 (5)
C3—C4—C5—C6	−55.7 (6)	C1—O1A—C7A—O2A	4.1 (6)
C4—C5—C6—C1	58.6 (5)	C1—O1A—C7A—C8A	−173.4 (4)
O1A—C1—C6—C5	−177.2 (4)	O2A—C7A—C8A—C9A	21.7 (7)
C2—C1—C6—C5	−58.6 (6)	O1A—C7A—C8A—C9A	−160.9 (4)
C3—C2—O1—C7	−87.2 (6)	O2A—C7A—C8A—C13A	−158.7 (5)
C1—C2—O1—C7	152.2 (5)	O1A—C7A—C8A—C13A	18.7 (6)
C2—O1—C7—O2	−4.5 (9)	C13A—C8A—C9A—C10A	0.2 (7)
C2—O1—C7—C8	176.4 (5)	C7A—C8A—C9A—C10A	179.7 (4)
O2—C7—C8—C13	−6.4 (9)	C13A—C8A—C9A—N1A	−175.1 (4)
O1—C7—C8—C13	172.7 (6)	C7A—C8A—C9A—N1A	4.5 (6)
O2—C7—C8—C9	173.8 (6)	C8A—C9A—C10A—C11A	0.6 (7)
O1—C7—C8—C9	−7.0 (8)	N1A—C9A—C10A—C11A	176.0 (4)
C13—C8—C9—C10	−1.8 (8)	C9A—C10A—C11A—C12A	−1.5 (7)
C7—C8—C9—C10	177.9 (6)	C10A—C11A—C12A—C13A	1.7 (8)
C13—C8—C9—N1	177.5 (6)	C11A—C12A—C13A—C8A	−1.0 (8)
C7—C8—C9—N1	−2.8 (8)	C9A—C8A—C13A—C12A	0.0 (7)
C8—C9—C10—C11	2.4 (9)	C7A—C8A—C13A—C12A	−179.6 (4)
N1—C9—C10—C11	−176.9 (6)	C10A—C9A—N1A—C25A	86.9 (6)
C9—C10—C11—C12	−2.3 (9)	C8A—C9A—N1A—C25A	−97.7 (5)
C10—C11—C12—C13	1.7 (10)	C10A—C9A—N1A—C14A	−101.8 (6)
C11—C12—C13—C8	−1.2 (11)	C8A—C9A—N1A—C14A	73.6 (6)
C9—C8—C13—C12	1.2 (10)	C25A—N1A—C14A—O3A	177.7 (5)
C7—C8—C13—C12	−178.5 (6)	C9A—N1A—C14A—O3A	6.8 (8)
C10—C9—N1—C14	−78.3 (6)	C25A—N1A—C14A—C15A	−1.6 (8)
C8—C9—N1—C14	102.4 (6)	C9A—N1A—C14A—C15A	−172.5 (5)
C10—C9—N1—C25	106.2 (6)	O3A—C14A—C15A—C16A	4.6 (10)
C8—C9—N1—C25	−73.1 (6)	N1A—C14A—C15A—C16A	−176.2 (6)
C25—N1—C14—O3	178.2 (4)	O3A—C14A—C15A—C24A	−176.9 (6)
C9—N1—C14—O3	3.0 (6)	N1A—C14A—C15A—C24A	2.3 (8)
C25—N1—C14—C15	−2.0 (6)	C24A—C15A—C16A—C17A	0.9 (9)
C9—N1—C14—C15	−177.1 (4)	C14A—C15A—C16A—C17A	179.4 (6)
O3—C14—C15—C16	1.6 (7)	C15A—C16A—C17A—C18A	−0.4 (10)
N1—C14—C15—C16	−178.3 (4)	C16A—C17A—C18A—C19A	−0.6 (10)
O3—C14—C15—C24	−177.5 (5)	C17A—C18A—C19A—C24A	1.2 (9)
N1—C14—C15—C24	2.7 (6)	C17A—C18A—C19A—C20A	179.8 (6)
C24—C15—C16—C17	0.5 (7)	C24A—C19A—C20A—C21A	−1.8 (8)
C14—C15—C16—C17	−178.5 (4)	C18A—C19A—C20A—C21A	179.5 (5)
C15—C16—C17—C18	−0.8 (7)	C19A—C20A—C21A—C22A	0.2 (9)
C16—C17—C18—C19	2.4 (7)	C20A—C21A—C22A—C23A	0.1 (9)
C17—C18—C19—C20	177.4 (5)	C21A—C22A—C23A—C24A	1.2 (8)
C17—C18—C19—C24	−3.6 (7)	C21A—C22A—C23A—C25A	−178.7 (5)
C18—C19—C20—C21	179.4 (5)	C18A—C19A—C24A—C15A	−0.7 (8)
C24—C19—C20—C21	0.4 (9)	C20A—C19A—C24A—C15A	−179.4 (5)
C19—C20—C21—C22	−0.7 (10)	C18A—C19A—C24A—C23A	−178.2 (5)
C20—C21—C22—C23	0.6 (10)	C20A—C19A—C24A—C23A	3.2 (8)
C21—C22—C23—C24	−0.3 (9)	C16A—C15A—C24A—C19A	−0.3 (8)
C21—C22—C23—C25	−179.9 (5)	C14A—C15A—C24A—C19A	−178.8 (5)
C22—C23—C24—C15	177.6 (5)	C16A—C15A—C24A—C23A	177.1 (5)
C25—C23—C24—C15	−2.8 (7)	C14A—C15A—C24A—C23A	−1.4 (8)
C22—C23—C24—C19	0.0 (7)	C22A—C23A—C24A—C19A	−2.8 (8)
C25—C23—C24—C19	179.7 (4)	C25A—C23A—C24A—C19A	177.1 (5)
C16—C15—C24—C23	−179.3 (4)	C22A—C23A—C24A—C15A	179.7 (5)
C14—C15—C24—C23	−0.3 (7)	C25A—C23A—C24A—C15A	−0.4 (7)
C16—C15—C24—C19	−1.7 (7)	C14A—N1A—C25A—O4A	179.5 (5)
C14—C15—C24—C19	177.3 (4)	C9A—N1A—C25A—O4A	−9.8 (8)
C18—C19—C24—C23	−179.1 (4)	C14A—N1A—C25A—C23A	−0.1 (8)
C20—C19—C24—C23	−0.1 (7)	C9A—N1A—C25A—C23A	170.5 (5)
C18—C19—C24—C15	3.3 (6)	C22A—C23A—C25A—O4A	1.4 (8)
C20—C19—C24—C15	−177.7 (5)	C24A—C23A—C25A—O4A	−178.5 (5)
C14—N1—C25—O4	−179.9 (4)	C22A—C23A—C25A—N1A	−179.0 (5)
C9—N1—C25—O4	−4.7 (6)	C24A—C23A—C25A—N1A	1.1 (7)
C14—N1—C25—C23	−1.0 (6)

(4) top

Crystal data top

C₄₄H₃₂O₆N₄·C₂H₆OS·H₂O	F(000) = 1693.1
M_r = 808.88	D_x = 1.338 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 2240 reflections
a = 22.374 (4) Å	θ = 4.0–25.0°
b = 9.319 (2) Å	µ = 0.14 mm⁻¹
c = 20.515 (4) Å	T = 130 K
β = 110.14 (3)°	Plate, colourless
V = 4015.9 (16) Å³	0.60 × 0.40 × 0.05 mm
Z = 4

Data collection top

Kuma KM4CCD κ-geometry diffractometer	3769 independent reflections
Radiation source: fine-focus sealed tube	3166 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
ω scans	θ_max = 25.0°, θ_min = 4.0°
Absorption correction: multi-scan SCALE3 ABSPACK.Oxford Diffraction program,2002.	h = −26→26
T_min = 0.882, T_max = 0.997	k = −10→11
13581 measured reflections	l = −22→24

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.078	w = 1/[σ²(F_o²) + (0.0343P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3769 reflections	Δρ_max = 0.21 e Å⁻³
549 parameters	Δρ_min = −0.20 e Å⁻³
13 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.05 (12)

Crystal data top

C₄₄H₃₂O₆N₄·C₂H₆OS·H₂O	V = 4015.9 (16) Å³
M_r = 808.88	Z = 4
Monoclinic, C2	Mo Kα radiation
a = 22.374 (4) Å	µ = 0.14 mm⁻¹
b = 9.319 (2) Å	T = 130 K
c = 20.515 (4) Å	0.60 × 0.40 × 0.05 mm
β = 110.14 (3)°

Data collection top

Kuma KM4CCD κ-geometry diffractometer	3769 independent reflections
Absorption correction: multi-scan SCALE3 ABSPACK.Oxford Diffraction program,2002.	3166 reflections with I > 2σ(I)
T_min = 0.882, T_max = 0.997	R_int = 0.053
13581 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.078	Δρ_max = 0.21 e Å⁻³
S = 1.04	Δρ_min = −0.20 e Å⁻³
3769 reflections	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
549 parameters	Absolute structure parameter: −0.05 (12)
13 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1S	0.26183 (7)	0.04156 (13)	0.18233 (7)	0.0376 (3)	0.88
O1S	0.2464 (3)	0.1996 (5)	0.1685 (3)	0.0409 (13)	0.88
C1S	0.3430 (2)	0.0309 (6)	0.2397 (3)	0.0439 (14)	0.88
H1S	0.3709	0.0585	0.2153	0.066*	0.88
H2S	0.3489	0.0945	0.2782	0.066*	0.88
H3S	0.3525	−0.0656	0.2564	0.066*	0.88
C2S	0.2257 (2)	−0.0160 (5)	0.2422 (2)	0.0531 (14)
H4S	0.1803	−0.0177	0.2200	0.080*	0.88
H5S	0.2406	−0.1104	0.2587	0.080*	0.88
H6S	0.2370	0.0497	0.2805	0.080*	0.88
S2S	0.2958 (6)	0.0662 (11)	0.2266 (5)	0.040 (3)	0.12
O2S	0.2651 (16)	0.199 (3)	0.1839 (19)	0.027 (11)*	0.12
C3S	0.3181 (15)	−0.038 (3)	0.1697 (17)	0.038 (9)*	0.12
O2	0.58178 (12)	0.3368 (3)	0.16090 (14)	0.0322 (7)
O1	0.55143 (12)	−0.0680 (3)	0.26693 (13)	0.0291 (7)
C1	0.56846 (16)	−0.1007 (4)	0.15982 (18)	0.0212 (9)
C2	0.56344 (18)	−0.2494 (4)	0.1609 (2)	0.0291 (10)
H2	0.5575	−0.2955	0.2001	0.035*
C3	0.56751 (18)	−0.3306 (4)	0.1050 (2)	0.0323 (10)
H3	0.5639	−0.4332	0.1059	0.039*
C4	0.57604 (18)	−0.2646 (4)	0.0496 (2)	0.0312 (10)
H4	0.5785	−0.3214	0.0115	0.037*
C5	0.58718 (16)	−0.0420 (5)	−0.0115 (2)	0.0296 (10)
H5	0.5880	−0.0963	−0.0510	0.036*
C6	0.59063 (18)	0.1039 (5)	−0.0130 (2)	0.0318 (10)
H6	0.5951	0.1511	−0.0527	0.038*
C7	0.58831 (17)	0.1855 (4)	0.0436 (2)	0.0272 (10)
H7	0.5908	0.2882	0.0420	0.033*
C8	0.58230 (16)	0.1199 (4)	0.10122 (18)	0.0202 (9)
C9	0.57793 (15)	−0.0321 (4)	0.10307 (18)	0.0186 (9)
C10	0.58143 (16)	−0.1143 (4)	0.04658 (19)	0.0240 (9)
C11	0.56343 (16)	−0.0165 (4)	0.2182 (2)	0.0220 (9)
C12	0.57977 (16)	0.2056 (4)	0.16004 (19)	0.0221 (9)
N1	0.57443 (13)	0.1316 (3)	0.21705 (14)	0.0181 (7)
C13	0.57293 (16)	0.2165 (4)	0.27570 (18)	0.0186 (8)
C14	0.51937 (15)	0.2957 (4)	0.27352 (17)	0.0187 (8)
C15	0.52226 (16)	0.3755 (4)	0.33176 (19)	0.0213 (9)
H15	0.4860	0.4316	0.3310	0.026*
C16	0.57630 (16)	0.3751 (4)	0.39107 (19)	0.0214 (8)
H16	0.5770	0.4285	0.4313	0.026*
C17	0.62901 (16)	0.2990 (4)	0.39176 (19)	0.0234 (9)
H17	0.6668	0.3002	0.4323	0.028*
C18	0.62791 (16)	0.2194 (4)	0.33391 (19)	0.0233 (9)
H18	0.6649	0.1665	0.3344	0.028*
C19	0.45977 (16)	0.2919 (4)	0.21087 (18)	0.0211 (8)
O3	0.44325 (11)	0.1828 (3)	0.17515 (13)	0.0267 (6)
C1A	0.45056 (17)	0.7657 (4)	0.41224 (18)	0.0195 (8)
C2A	0.51044 (16)	0.7480 (4)	0.40899 (18)	0.0217 (9)
H2A	0.5263	0.6529	0.4074	0.026*
C3A	0.54818 (16)	0.8681 (4)	0.40802 (18)	0.0243 (9)
H3A	0.5900	0.8551	0.4058	0.029*
C4A	0.52607 (17)	1.0038 (4)	0.41060 (17)	0.0251 (9)
H4A	0.5518	1.0852	0.4090	0.030*
C5A	0.44035 (18)	1.1650 (4)	0.41995 (19)	0.0287 (10)
H5A	0.4655	1.2484	0.4198	0.034*
C6A	0.38173 (18)	1.1813 (4)	0.42587 (19)	0.0281 (10)
H6A	0.3668	1.2758	0.4310	0.034*
C7A	0.34403 (17)	1.0615 (4)	0.42542 (18)	0.0266 (9)
H7A	0.3022	1.0739	0.4278	0.032*
C8A	0.36550 (16)	0.9255 (4)	0.41991 (18)	0.0194 (8)
C9A	0.42682 (17)	0.9048 (4)	0.41545 (18)	0.0198 (8)
C10A	0.46496 (16)	1.0267 (4)	0.41507 (17)	0.0217 (8)
C11A	0.41058 (17)	0.6389 (4)	0.40964 (18)	0.0222 (9)
C12A	0.32397 (17)	0.8013 (4)	0.41570 (18)	0.0230 (9)
O1A	0.42761 (11)	0.5159 (3)	0.40671 (13)	0.0301 (7)
O2A	0.26981 (12)	0.8121 (3)	0.41679 (13)	0.0310 (7)
N1A	0.34856 (13)	0.6649 (3)	0.41005 (14)	0.0178 (7)
C13A	0.30271 (15)	0.5490 (4)	0.38942 (18)	0.0202 (8)
C14A	0.28144 (15)	0.4984 (4)	0.32101 (18)	0.0197 (8)
C15A	0.23462 (16)	0.3912 (4)	0.30367 (19)	0.0240 (9)
H15A	0.2180	0.3566	0.2568	0.029*
C16A	0.21104 (17)	0.3361 (4)	0.3531 (2)	0.0279 (10)
H16A	0.1792	0.2622	0.3404	0.034*
C17A	0.23342 (16)	0.3864 (4)	0.4201 (2)	0.0252 (9)
H17A	0.2172	0.3474	0.4540	0.030*
C18A	0.27978 (16)	0.4932 (4)	0.43851 (19)	0.0228 (9)
H18A	0.2957	0.5288	0.4853	0.027*
C19A	0.30576 (16)	0.5595 (4)	0.26644 (18)	0.0224 (9)
O3A	0.32622 (12)	0.6843 (3)	0.27135 (13)	0.0308 (6)
N2	0.42492 (13)	0.4138 (3)	0.19772 (14)	0.0199 (7)
H2N	0.4422	0.5040	0.2220	0.024*
N2A	0.30285 (12)	0.4734 (3)	0.21312 (14)	0.0209 (7)
H2NA	0.2906	0.3751	0.2176	0.025*
C21	0.36611 (16)	0.4247 (4)	0.13762 (17)	0.0202 (9)
H21	0.3476	0.3308	0.1271	0.024*
C22	0.31785 (15)	0.5237 (4)	0.15297 (16)	0.0205 (8)
H22	0.3361	0.6178	0.1629	0.025*
C23	0.25701 (16)	0.5331 (5)	0.08933 (17)	0.0308 (9)
H23A	0.2274	0.5976	0.0985	0.037*
H23B	0.2378	0.4397	0.0806	0.037*
C24	0.27076 (17)	0.5838 (4)	0.02541 (19)	0.0358 (11)
H24A	0.2862	0.6807	0.0325	0.043*
H24B	0.2322	0.5827	−0.0141	0.043*
C25	0.31989 (17)	0.4890 (4)	0.01058 (19)	0.0311 (10)
H25A	0.3296	0.5260	−0.0283	0.037*
H25B	0.3029	0.3940	−0.0009	0.037*
C26	0.38028 (16)	0.4802 (4)	0.07450 (17)	0.0237 (9)
H26A	0.4108	0.4190	0.0651	0.028*
H26B	0.3984	0.5745	0.0848	0.028*
O1W	0.44891 (13)	0.7142 (3)	0.23985 (14)	0.0379 (7)
H1W	0.4145	0.7372	0.2574	0.045*
H2W	0.4804	0.7916	0.2493	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1S	0.0559 (8)	0.0233 (7)	0.0282 (8)	−0.0060 (6)	0.0077 (7)	−0.0024 (7)
O1S	0.045 (3)	0.025 (2)	0.040 (3)	−0.003 (2)	−0.001 (3)	0.0081 (18)
C1S	0.028 (3)	0.044 (3)	0.059 (4)	0.002 (3)	0.014 (3)	0.017 (3)
C2S	0.042 (3)	0.046 (3)	0.067 (4)	−0.006 (2)	0.012 (2)	0.023 (3)
S2S	0.057 (7)	0.043 (6)	0.007 (5)	−0.021 (6)	−0.007 (5)	−0.008 (5)
O2	0.0468 (18)	0.0204 (17)	0.0328 (18)	−0.0012 (13)	0.0181 (14)	0.0011 (13)
O1	0.0441 (16)	0.0240 (15)	0.0239 (16)	−0.0033 (13)	0.0177 (13)	0.0020 (13)
C1	0.019 (2)	0.023 (2)	0.021 (2)	0.0001 (16)	0.0065 (17)	−0.0052 (18)
C2	0.036 (2)	0.020 (2)	0.031 (3)	0.0015 (18)	0.011 (2)	0.0015 (19)
C3	0.041 (2)	0.020 (2)	0.034 (3)	0.0028 (19)	0.009 (2)	−0.009 (2)
C4	0.036 (2)	0.031 (3)	0.027 (3)	0.0093 (19)	0.011 (2)	−0.009 (2)
C5	0.023 (2)	0.044 (3)	0.022 (3)	0.0045 (19)	0.0071 (18)	−0.006 (2)
C6	0.030 (2)	0.045 (3)	0.022 (3)	0.004 (2)	0.012 (2)	0.007 (2)
C7	0.026 (2)	0.027 (2)	0.029 (3)	0.0049 (18)	0.0110 (19)	0.009 (2)
C8	0.019 (2)	0.027 (2)	0.016 (2)	0.0039 (17)	0.0086 (17)	0.0041 (18)
C9	0.0170 (18)	0.021 (2)	0.018 (2)	0.0022 (16)	0.0056 (16)	−0.0013 (17)
C10	0.019 (2)	0.031 (2)	0.020 (2)	0.0051 (17)	0.0039 (17)	0.0007 (19)
C11	0.020 (2)	0.020 (2)	0.025 (2)	0.0002 (16)	0.0054 (18)	0.0019 (18)
C12	0.0212 (19)	0.020 (2)	0.026 (2)	0.0026 (17)	0.0095 (17)	0.0040 (19)
N1	0.0220 (16)	0.0164 (17)	0.0173 (18)	−0.0013 (13)	0.0086 (14)	−0.0034 (14)
C13	0.024 (2)	0.014 (2)	0.019 (2)	−0.0013 (16)	0.0090 (17)	−0.0014 (17)
C14	0.020 (2)	0.017 (2)	0.017 (2)	−0.0009 (16)	0.0038 (16)	0.0013 (17)
C15	0.0199 (19)	0.016 (2)	0.028 (2)	0.0034 (16)	0.0093 (17)	0.0009 (18)
C16	0.023 (2)	0.020 (2)	0.021 (2)	0.0001 (16)	0.0066 (17)	−0.0051 (17)
C17	0.0202 (19)	0.025 (2)	0.024 (2)	−0.0024 (17)	0.0054 (17)	−0.0018 (18)
C18	0.0183 (19)	0.021 (2)	0.031 (2)	0.0018 (16)	0.0099 (18)	0.0014 (19)
C19	0.023 (2)	0.022 (2)	0.022 (2)	−0.0022 (18)	0.0117 (17)	0.0013 (19)
O3	0.0264 (14)	0.0242 (15)	0.0283 (16)	−0.0006 (12)	0.0078 (12)	−0.0063 (13)
C1A	0.022 (2)	0.018 (2)	0.016 (2)	−0.0004 (16)	0.0039 (16)	0.0016 (16)
C2A	0.020 (2)	0.024 (2)	0.020 (2)	0.0017 (16)	0.0060 (17)	−0.0009 (17)
C3A	0.0184 (19)	0.035 (3)	0.020 (2)	0.0021 (18)	0.0082 (16)	−0.0008 (19)
C4A	0.028 (2)	0.028 (3)	0.020 (2)	−0.0079 (18)	0.0090 (17)	−0.0002 (18)
C5A	0.031 (2)	0.022 (2)	0.032 (3)	−0.0038 (18)	0.010 (2)	0.0011 (19)
C6A	0.033 (2)	0.021 (2)	0.031 (3)	0.0028 (19)	0.0116 (19)	0.0003 (18)
C7A	0.025 (2)	0.026 (2)	0.031 (2)	0.0050 (18)	0.0118 (17)	0.0008 (19)
C8A	0.0223 (19)	0.020 (2)	0.016 (2)	0.0022 (16)	0.0068 (16)	0.0018 (16)
C9A	0.025 (2)	0.024 (2)	0.010 (2)	−0.0005 (17)	0.0052 (16)	0.0009 (17)
C10A	0.0220 (19)	0.025 (2)	0.018 (2)	0.0005 (18)	0.0068 (16)	−0.0007 (18)
C11A	0.024 (2)	0.028 (2)	0.015 (2)	0.0025 (18)	0.0070 (17)	0.0001 (18)
C12A	0.022 (2)	0.029 (2)	0.018 (2)	0.0030 (18)	0.0078 (17)	−0.0006 (18)
O1A	0.0257 (14)	0.0202 (17)	0.0482 (18)	0.0041 (12)	0.0176 (13)	−0.0007 (13)
O2A	0.0234 (14)	0.0284 (16)	0.0464 (18)	0.0001 (12)	0.0188 (13)	−0.0064 (13)
N1A	0.0166 (15)	0.0163 (17)	0.0214 (18)	0.0000 (13)	0.0077 (13)	0.0006 (13)
C13A	0.0182 (18)	0.0153 (19)	0.030 (2)	0.0016 (16)	0.0119 (16)	−0.0017 (19)
C14A	0.0184 (18)	0.019 (2)	0.022 (2)	0.0007 (16)	0.0078 (16)	0.0003 (16)
C15A	0.0223 (19)	0.024 (2)	0.027 (2)	0.0021 (17)	0.0101 (17)	−0.0024 (18)
C16A	0.023 (2)	0.025 (2)	0.038 (3)	−0.0034 (17)	0.0130 (19)	0.001 (2)
C17A	0.025 (2)	0.023 (2)	0.032 (3)	0.0035 (17)	0.0153 (18)	0.0066 (19)
C18A	0.0207 (19)	0.025 (2)	0.023 (2)	0.0025 (17)	0.0079 (17)	0.0021 (17)
C19A	0.0179 (19)	0.024 (2)	0.024 (2)	0.0023 (17)	0.0049 (16)	0.0030 (19)
O3A	0.0446 (16)	0.0224 (16)	0.0311 (17)	−0.0088 (13)	0.0203 (13)	−0.0030 (12)
N2	0.0182 (16)	0.0162 (17)	0.0226 (18)	−0.0005 (13)	0.0039 (14)	−0.0022 (14)
N2A	0.0217 (16)	0.0222 (17)	0.0209 (18)	−0.0002 (14)	0.0102 (14)	0.0015 (15)
C21	0.0188 (19)	0.021 (2)	0.018 (2)	−0.0012 (16)	0.0031 (16)	−0.0039 (17)
C22	0.0232 (19)	0.021 (2)	0.017 (2)	−0.0013 (16)	0.0072 (15)	0.0021 (17)
C23	0.023 (2)	0.039 (2)	0.030 (2)	0.0064 (19)	0.0084 (17)	0.008 (2)
C24	0.027 (2)	0.046 (3)	0.029 (2)	0.0026 (19)	0.0036 (19)	0.009 (2)
C25	0.033 (2)	0.038 (3)	0.022 (2)	−0.0037 (19)	0.0093 (18)	0.0036 (19)
C26	0.025 (2)	0.025 (2)	0.023 (2)	−0.0016 (17)	0.0103 (17)	−0.0005 (18)
O1W	0.0380 (16)	0.0330 (16)	0.0488 (19)	−0.0090 (13)	0.0230 (14)	−0.0120 (14)

Geometric parameters (Å, º) top

S1S—O1S	1.517 (4)	C3A—C4A	1.365 (5)
S1S—C2S	1.769 (4)	C3A—H3A	0.9599
S1S—C1S	1.794 (5)	C4A—C10A	1.418 (5)
C1S—H1S	0.9600	C4A—H4A	0.9598
C1S—H2S	0.9601	C5A—C6A	1.367 (5)
C1S—H3S	0.9600	C5A—C10A	1.419 (5)
C2S—S2S	1.868 (12)	C5A—H5A	0.9600
C2S—H4S	0.9600	C6A—C7A	1.398 (5)
C2S—H5S	0.9600	C6A—H6A	0.9597
C2S—H6S	0.9599	C7A—C8A	1.374 (5)
S2S—O2S	1.53 (2)	C7A—H7A	0.9601
S2S—C3S	1.72 (3)	C8A—C9A	1.419 (5)
O2—C12	1.223 (4)	C8A—C12A	1.468 (5)
O1—C11	1.220 (4)	C9A—C10A	1.422 (5)
C1—C2	1.391 (5)	C11A—O1A	1.216 (4)
C1—C9	1.406 (5)	C11A—N1A	1.412 (4)
C1—C11	1.468 (5)	C12A—O2A	1.224 (4)
C2—C3	1.403 (5)	C12A—N1A	1.405 (4)
C2—H2	0.9599	N1A—C13A	1.449 (4)
C3—C4	1.362 (5)	C13A—C18A	1.380 (5)
C3—H3	0.9599	C13A—C14A	1.399 (5)
C4—C10	1.408 (5)	C14A—C15A	1.402 (5)
C4—H4	0.9598	C14A—C19A	1.514 (5)
C5—C6	1.363 (5)	C15A—C16A	1.392 (5)
C5—C10	1.413 (5)	C15A—H15A	0.9599
C5—H5	0.9603	C16A—C17A	1.374 (5)
C6—C7	1.403 (5)	C16A—H16A	0.9601
C6—H6	0.9600	C17A—C18A	1.393 (5)
C7—C8	1.379 (5)	C17A—H17A	0.9603
C7—H7	0.9600	C18A—H18A	0.9600
C8—C9	1.421 (5)	C19A—O3A	1.241 (4)
C8—C12	1.465 (5)	C19A—N2A	1.340 (4)
C9—C10	1.414 (5)	N2—C21	1.464 (4)
C11—N1	1.403 (4)	N2—H2N	0.9858
C12—N1	1.398 (4)	N2A—C22	1.463 (4)
N1—C13	1.450 (4)	N2A—H2NA	0.9698
C13—C18	1.389 (5)	C21—C26	1.526 (5)
C13—C14	1.395 (5)	C21—C22	1.533 (5)
C14—C15	1.390 (5)	C21—H21	0.9601
C14—C19	1.500 (5)	C22—C23	1.530 (4)
C15—C16	1.389 (5)	C22—H22	0.9600
C15—H15	0.9600	C23—C24	1.522 (5)
C16—C17	1.372 (5)	C23—H23A	0.9601
C16—H16	0.9597	C23—H23B	0.9599
C17—C18	1.392 (5)	C24—C25	1.520 (5)
C17—H17	0.9600	C24—H24A	0.9600
C18—H18	0.9602	C24—H24B	0.9601
C19—O3	1.233 (4)	C25—C26	1.527 (5)
C19—N2	1.352 (4)	C25—H25A	0.9601
C1A—C2A	1.374 (5)	C25—H25B	0.9600
C1A—C9A	1.410 (5)	C26—H26A	0.9599
C1A—C11A	1.472 (5)	C26—H26B	0.9600
C2A—C3A	1.407 (5)	O1W—H1W	0.9800
C2A—H2A	0.9600	O1W—H2W	0.9800

O1S—S1S—C2S	107.2 (3)	C6A—C5A—H5A	119.4
O1S—S1S—C1S	106.9 (3)	C10A—C5A—H5A	119.6
C2S—S1S—C1S	97.4 (2)	C5A—C6A—C7A	120.4 (4)
S1S—C1S—H1S	109.7	C5A—C6A—H6A	119.5
S1S—C1S—H2S	109.1	C7A—C6A—H6A	120.1
H1S—C1S—H2S	109.5	C8A—C7A—C6A	120.7 (3)
S1S—C1S—H3S	109.6	C8A—C7A—H7A	119.3
H1S—C1S—H3S	109.5	C6A—C7A—H7A	119.9
H2S—C1S—H3S	109.5	C7A—C8A—C9A	120.3 (3)
S1S—C2S—H4S	109.8	C7A—C8A—C12A	120.0 (3)
S1S—C2S—H5S	109.8	C9A—C8A—C12A	119.7 (3)
H4S—C2S—H5S	109.5	C1A—C9A—C8A	121.1 (3)
S1S—C2S—H6S	108.8	C1A—C9A—C10A	119.8 (3)
H4S—C2S—H6S	109.5	C8A—C9A—C10A	119.1 (3)
H5S—C2S—H6S	109.5	C4A—C10A—C5A	123.2 (3)
O2S—S2S—C3S	104.1 (18)	C4A—C10A—C9A	118.3 (3)
O2S—S2S—C2S	101.0 (15)	C5A—C10A—C9A	118.5 (3)
C3S—S2S—C2S	110.0 (12)	O1A—C11A—N1A	119.2 (3)
C2—C1—C9	120.1 (3)	O1A—C11A—C1A	124.2 (3)
C2—C1—C11	119.4 (3)	N1A—C11A—C1A	116.6 (3)
C9—C1—C11	120.5 (3)	O2A—C12A—N1A	119.6 (3)
C1—C2—C3	119.8 (4)	O2A—C12A—C8A	123.0 (3)
C1—C2—H2	119.6	N1A—C12A—C8A	117.4 (3)
C3—C2—H2	120.6	C12A—N1A—C11A	124.7 (3)
C4—C3—C2	120.4 (4)	C12A—N1A—C13A	116.1 (3)
C4—C3—H3	120.2	C11A—N1A—C13A	118.0 (3)
C2—C3—H3	119.4	C18A—C13A—C14A	121.4 (3)
C3—C4—C10	121.6 (4)	C18A—C13A—N1A	118.1 (3)
C3—C4—H4	119.5	C14A—C13A—N1A	120.4 (3)
C10—C4—H4	118.9	C13A—C14A—C15A	117.4 (3)
C6—C5—C10	121.1 (4)	C13A—C14A—C19A	122.0 (3)
C6—C5—H5	119.3	C15A—C14A—C19A	120.5 (3)
C10—C5—H5	119.6	C16A—C15A—C14A	121.0 (3)
C5—C6—C7	120.2 (4)	C16A—C15A—H15A	119.5
C5—C6—H6	119.9	C14A—C15A—H15A	119.4
C7—C6—H6	119.8	C17A—C16A—C15A	120.3 (3)
C8—C7—C6	120.8 (4)	C17A—C16A—H16A	119.7
C8—C7—H7	119.7	C15A—C16A—H16A	120.0
C6—C7—H7	119.6	C16A—C17A—C18A	119.7 (3)
C7—C8—C9	119.5 (4)	C16A—C17A—H17A	119.9
C7—C8—C12	120.5 (4)	C18A—C17A—H17A	120.4
C9—C8—C12	120.0 (3)	C13A—C18A—C17A	120.1 (4)
C1—C9—C10	119.9 (3)	C13A—C18A—H18A	119.7
C1—C9—C8	120.4 (3)	C17A—C18A—H18A	120.2
C10—C9—C8	119.6 (4)	O3A—C19A—N2A	122.7 (3)
C4—C10—C5	123.0 (4)	O3A—C19A—C14A	120.6 (3)
C4—C10—C9	118.2 (3)	N2A—C19A—C14A	116.7 (3)
C5—C10—C9	118.7 (4)	C19—N2—C21	121.0 (3)
O1—C11—N1	119.4 (3)	C19—N2—H2N	121.2
O1—C11—C1	123.9 (3)	C21—N2—H2N	116.6
N1—C11—C1	116.7 (4)	C19A—N2A—C22	122.4 (3)
O2—C12—N1	119.6 (3)	C19A—N2A—H2NA	115.1
O2—C12—C8	123.1 (3)	C22—N2A—H2NA	122.5
N1—C12—C8	117.3 (3)	N2—C21—C26	110.4 (3)
C12—N1—C11	124.4 (3)	N2—C21—C22	111.2 (3)
C12—N1—C13	117.2 (3)	C26—C21—C22	109.7 (3)
C11—N1—C13	117.9 (3)	N2—C21—H21	108.6
C18—C13—C14	120.9 (3)	C26—C21—H21	108.5
C18—C13—N1	117.2 (3)	C22—C21—H21	108.4
C14—C13—N1	121.8 (3)	N2A—C22—C23	110.1 (3)
C15—C14—C13	118.1 (3)	N2A—C22—C21	111.3 (3)
C15—C14—C19	120.9 (3)	C23—C22—C21	110.0 (3)
C13—C14—C19	121.0 (3)	N2A—C22—H22	108.6
C16—C15—C14	121.4 (3)	C23—C22—H22	108.5
C16—C15—H15	119.4	C21—C22—H22	108.3
C14—C15—H15	119.2	C24—C23—C22	111.6 (3)
C17—C16—C15	119.7 (3)	C24—C23—H23A	109.4
C17—C16—H16	120.0	C22—C23—H23A	109.9
C15—C16—H16	120.2	C24—C23—H23B	109.3
C16—C17—C18	120.2 (3)	C22—C23—H23B	108.4
C16—C17—H17	120.0	H23A—C23—H23B	108.1
C18—C17—H17	119.7	C25—C24—C23	111.5 (3)
C13—C18—C17	119.6 (3)	C25—C24—H24A	109.2
C13—C18—H18	120.2	C23—C24—H24A	109.3
C17—C18—H18	120.2	C25—C24—H24B	109.1
O3—C19—N2	122.7 (3)	C23—C24—H24B	109.6
O3—C19—C14	121.7 (3)	H24A—C24—H24B	108.0
N2—C19—C14	115.6 (3)	C24—C25—C26	110.3 (3)
C2A—C1A—C9A	120.1 (3)	C24—C25—H25A	110.1
C2A—C1A—C11A	119.5 (3)	C26—C25—H25A	110.3
C9A—C1A—C11A	120.3 (3)	C24—C25—H25B	109.4
C1A—C2A—C3A	120.3 (3)	C26—C25—H25B	108.7
C1A—C2A—H2A	119.4	H25A—C25—H25B	108.1
C3A—C2A—H2A	120.2	C21—C26—C25	111.5 (3)
C4A—C3A—C2A	120.6 (3)	C21—C26—H26A	109.8
C4A—C3A—H3A	119.4	C25—C26—H26A	109.9
C2A—C3A—H3A	120.0	C21—C26—H26B	108.6
C3A—C4A—C10A	120.8 (3)	C25—C26—H26B	108.8
C3A—C4A—H4A	120.0	H26A—C26—H26B	108.2
C10A—C4A—H4A	119.2	H1W—O1W—H2W	111.7
C6A—C5A—C10A	121.0 (4)

C9—C1—C2—C3	−0.4 (6)	C2A—C1A—C9A—C10A	0.2 (5)
C11—C1—C2—C3	179.3 (3)	C11A—C1A—C9A—C10A	−177.4 (3)
C1—C2—C3—C4	−0.3 (6)	C7A—C8A—C9A—C1A	177.7 (3)
C2—C3—C4—C10	0.4 (6)	C12A—C8A—C9A—C1A	−4.8 (5)
C10—C5—C6—C7	−0.2 (6)	C7A—C8A—C9A—C10A	−1.5 (5)
C5—C6—C7—C8	−0.2 (6)	C12A—C8A—C9A—C10A	176.0 (3)
C6—C7—C8—C9	−0.5 (5)	C3A—C4A—C10A—C5A	178.1 (4)
C6—C7—C8—C12	−179.9 (3)	C3A—C4A—C10A—C9A	−1.2 (5)
C2—C1—C9—C10	0.9 (5)	C6A—C5A—C10A—C4A	−178.4 (3)
C11—C1—C9—C10	−178.7 (3)	C6A—C5A—C10A—C9A	0.9 (5)
C2—C1—C9—C8	179.2 (3)	C1A—C9A—C10A—C4A	0.7 (5)
C11—C1—C9—C8	−0.5 (5)	C8A—C9A—C10A—C4A	180.0 (3)
C7—C8—C9—C1	−176.7 (3)	C1A—C9A—C10A—C5A	−178.6 (3)
C12—C8—C9—C1	2.7 (5)	C8A—C9A—C10A—C5A	0.7 (5)
C7—C8—C9—C10	1.6 (5)	C2A—C1A—C11A—O1A	2.2 (5)
C12—C8—C9—C10	−179.0 (3)	C9A—C1A—C11A—O1A	179.9 (3)
C3—C4—C10—C5	−176.8 (4)	C2A—C1A—C11A—N1A	−177.2 (3)
C3—C4—C10—C9	0.2 (6)	C9A—C1A—C11A—N1A	0.4 (5)
C6—C5—C10—C4	178.3 (4)	C7A—C8A—C12A—O2A	0.1 (5)
C6—C5—C10—C9	1.3 (6)	C9A—C8A—C12A—O2A	−177.4 (3)
C1—C9—C10—C4	−0.8 (5)	C7A—C8A—C12A—N1A	179.9 (3)
C8—C9—C10—C4	−179.1 (3)	C9A—C8A—C12A—N1A	2.5 (5)
C1—C9—C10—C5	176.3 (3)	O2A—C12A—N1A—C11A	−178.7 (3)
C8—C9—C10—C5	−2.0 (5)	C8A—C12A—N1A—C11A	1.4 (5)
C2—C1—C11—O1	−4.3 (5)	O2A—C12A—N1A—C13A	14.2 (5)
C9—C1—C11—O1	175.4 (3)	C8A—C12A—N1A—C13A	−165.7 (3)
C2—C1—C11—N1	174.6 (3)	O1A—C11A—N1A—C12A	177.7 (3)
C9—C1—C11—N1	−5.8 (5)	C1A—C11A—N1A—C12A	−2.8 (5)
C7—C8—C12—O2	1.2 (5)	O1A—C11A—N1A—C13A	−15.4 (5)
C9—C8—C12—O2	−178.2 (3)	C1A—C11A—N1A—C13A	164.1 (3)
C7—C8—C12—N1	−179.2 (3)	C12A—N1A—C13A—C18A	−76.8 (4)
C9—C8—C12—N1	1.4 (5)	C11A—N1A—C13A—C18A	115.2 (4)
O2—C12—N1—C11	171.3 (3)	C12A—N1A—C13A—C14A	101.7 (4)
C8—C12—N1—C11	−8.3 (5)	C11A—N1A—C13A—C14A	−66.3 (4)
O2—C12—N1—C13	−1.3 (5)	C18A—C13A—C14A—C15A	1.6 (5)
C8—C12—N1—C13	179.1 (3)	N1A—C13A—C14A—C15A	−176.8 (3)
O1—C11—N1—C12	−170.7 (3)	C18A—C13A—C14A—C19A	179.5 (3)
C1—C11—N1—C12	10.4 (5)	N1A—C13A—C14A—C19A	1.1 (5)
O1—C11—N1—C13	1.9 (5)	C13A—C14A—C15A—C16A	−0.9 (5)
C1—C11—N1—C13	−177.0 (3)	C19A—C14A—C15A—C16A	−178.8 (3)
C12—N1—C13—C18	−104.3 (4)	C14A—C15A—C16A—C17A	0.0 (5)
C11—N1—C13—C18	82.6 (4)	C15A—C16A—C17A—C18A	0.2 (5)
C12—N1—C13—C14	73.9 (4)	C14A—C13A—C18A—C17A	−1.5 (5)
C11—N1—C13—C14	−99.2 (4)	N1A—C13A—C18A—C17A	177.0 (3)
C18—C13—C14—C15	−1.2 (5)	C16A—C17A—C18A—C13A	0.5 (5)
N1—C13—C14—C15	−179.3 (3)	C13A—C14A—C19A—O3A	−26.2 (5)
C18—C13—C14—C19	−179.6 (3)	C15A—C14A—C19A—O3A	151.6 (3)
N1—C13—C14—C19	2.4 (5)	C13A—C14A—C19A—N2A	155.0 (3)
C13—C14—C15—C16	−1.1 (5)	C15A—C14A—C19A—N2A	−27.3 (5)
C19—C14—C15—C16	177.3 (3)	O3—C19—N2—C21	−2.6 (5)
C14—C15—C16—C17	2.4 (5)	C14—C19—N2—C21	179.2 (3)
C15—C16—C17—C18	−1.6 (5)	O3A—C19A—N2A—C22	−6.0 (5)
C14—C13—C18—C17	2.0 (5)	C14A—C19A—N2A—C22	172.9 (3)
N1—C13—C18—C17	−179.8 (3)	C19—N2—C21—C26	−90.0 (4)
C16—C17—C18—C13	−0.6 (5)	C19—N2—C21—C22	148.0 (3)
C15—C14—C19—O3	−145.0 (3)	C19A—N2A—C22—C23	−108.9 (4)
C13—C14—C19—O3	33.4 (5)	C19A—N2A—C22—C21	128.9 (3)
C15—C14—C19—N2	33.2 (5)	N2—C21—C22—N2A	−57.8 (4)
C13—C14—C19—N2	−148.5 (3)	C26—C21—C22—N2A	179.8 (3)
C9A—C1A—C2A—C3A	−0.7 (5)	N2—C21—C22—C23	179.9 (3)
C11A—C1A—C2A—C3A	176.9 (3)	C26—C21—C22—C23	57.5 (4)
C1A—C2A—C3A—C4A	0.3 (5)	N2A—C22—C23—C24	−179.4 (3)
C2A—C3A—C4A—C10A	0.7 (5)	C21—C22—C23—C24	−56.5 (4)
C10A—C5A—C6A—C7A	−1.7 (6)	C22—C23—C24—C25	55.5 (4)
C5A—C6A—C7A—C8A	0.8 (6)	C23—C24—C25—C26	−54.9 (4)
C6A—C7A—C8A—C9A	0.8 (5)	N2—C21—C26—C25	178.6 (3)
C6A—C7A—C8A—C12A	−176.7 (4)	C22—C21—C26—C25	−58.6 (4)
C2A—C1A—C9A—C8A	−179.0 (3)	C24—C25—C26—C21	57.0 (4)
C11A—C1A—C9A—C8A	3.3 (5)

Experimental details

	(1)	(2)	(3)	(4)
Crystal data
Chemical formula	C₄₁H₂₆N₂O₈	C₄₃H₃₀N₂O₈	C₄₄H₃₀N₂O₈	C₄₄H₃₂O₆N₄·C₂H₆OS·H₂O
M_r	674.64	702.69	714.70	808.88
Crystal system, space group	Monoclinic, C2	Triclinic, P1	Trigonal, P3₂21	Monoclinic, C2
Temperature (K)	100	140	140	130
a, b, c (Å)	16.9672 (9), 8.0833 (3), 25.0204 (5)	9.2897 (7), 10.0849 (7), 11.0897 (8)	11.873 (2), 11.873 (2), 43.046 (9)	22.374 (4), 9.319 (2), 20.515 (4)
α, β, γ (°)	90, 116.312 (3), 90	103.203 (6), 111.486 (7), 107.147 (6)	90, 90, 120	90, 110.14 (3), 90
V (Å³)	3076.0 (2)	855.11 (14)	5255.1 (17)	4015.9 (16)
Z	4	1	6	4
Radiation type	Cu Kα	Mo Kα	Mo Kα	Mo Kα
µ (mm⁻¹)	0.84	0.10	0.09	0.14
Crystal size (mm)	0.30 × 0.10 × 0.05	0.30 × 0.20 × 0.10	0.5 × 0.2 × 0.2	0.60 × 0.40 × 0.05

Data collection
Diffractometer	Xcalibur Nova κ-geometry diffractometer	Kuma KM4CCD κ-geometry diffractometer	Kuma KM4CCD κ-geometry diffractometer	Kuma KM4CCD κ-geometry diffractometer
Absorption correction	Multi-scan SCALE3 ABSPACK.Oxford Diffraction program,2005.	–	–	Multi-scan SCALE3 ABSPACK.Oxford Diffraction program,2002.
T_min, T_max	0.765, 0.954	–	–	0.882, 0.997
No. of measured, independent and observed [I > 2σ(I)] reflections	26986, 2810, 2765	8911, 2994, 2388	15932, 3556, 2230	13581, 3769, 3166
R_int	0.048	0.034	0.081	0.053
(sin θ/λ)_max (Å⁻¹)	0.592	0.595	0.595	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.089, 0.247, 1.03	0.031, 0.058, 0.91	0.051, 0.126, 0.97	0.047, 0.078, 1.04
No. of reflections	2810	2994	3556	3769
No. of parameters	506	479	487	549
No. of restraints	31	3	0	13
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.1555P)² + 10.4492P] where P = (F_o² + 2F_c²)/3	w = 1/[σ²(F_o²) + (0.030P)²] where P = (F_o² + 2F_c²)/3	w = 1/[σ²(F_o²) + (0.0564P)²] where P = (F_o² + 2F_c²)/3	w = 1/[σ²(F_o²) + (0.0343P)²] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.41	0.16, −0.18	0.25, −0.28	0.21, −0.20
Absolute structure	Flack H D (1983), Acta Cryst. A39, 876-881	Flack H D (1983), Acta Cryst. A39, 876-881	Flack H D (1983), Acta Cryst. A39, 876-881	Flack H D (1983), Acta Cryst. A39, 876-881
Absolute structure parameter	0.0 (10)	0 (10)	0 (10)	−0.05 (12)

Computer programs: CrysAlis CCD v.1.171.32.5(Oxford Diffraction,2007), CrysAlis CCD v.1.171.23(Oxford Diffraction,2002), CrysAlis RED v.1.171.32.5(Oxford Diffraction,2007), CrysAlis RED v.1.171.23(Oxford Diffraction,2002), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP. Simens Analytical X-Ray Instruments (1989).

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