Tailoring the dimensionality of metal complexes via ligand modifications

Le Garff, P.; Maria Losus, R.; Chaudhary, S.; Dobrzańska, L.

doi:10.1107/S2052520623010260

Tailoring the dimensionality of metal complexes via ligand modifications

P. Le Garff, R. Maria Losus, S. Chaudhary and L. Dobrzańska

A series of Cu^II complexes obtained under the same reaction conditions has been analyzed to gain insight into the effect of the ligand composition on the final reaction product. Dipodal ligands containing N-donor imidazole rings and a benzene ring as a spacer with different numbers of methyl substituents on the aromatic rings were selected for the study such as 1,3-bis(imidazol-1-ylmethyl)benzene (L1), 1,3-bis(imidazol-1-ylmethyl)-5-methylbenzene (L2), 1,3-bis(imidazol-1-ylmethyl)-2,4,6-trimethylbenzene (L3), 1,3-bis(2-methylimidazol-1-ylmethyl)-2,4,6-trimethylbenzene (L4). L4 has not been reported previously and was synthesized for this study. The formed metal complexes show the presence of polymeric (ligand with no or one methyl substituent; 1–4), or discrete motifs (3- or 5-methyl substituents; 5–7). The new metal complexes 3, 5 and 6 were analyzed using single-crystal X-ray diffraction and powder diffraction. In addition, the structural analyses were supported by computational methods.

Keywords: dipodal ligands; coordination polymers; crystal engineering; discrete metal complexes.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520623010260/yv5014sup1.cif Contains datablocks 3, 5, 6
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520623010260/yv50143sup2.hkl Contains datablock 3
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520623010260/yv50145sup3.hkl Contains datablock 5
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520623010260/yv50146sup4.hkl Contains datablock 6
	Portable Document Format (PDF) file https://doi.org/10.1107/S2052520623010260/yv5014sup5.pdf Supplementary material

CCDC references: 2285796; 2285797; 2285798

Computing details top

(3) top

Crystal data top

C₃₀H₃₂CuN₁₀O₆	Z = 1
M_r = 692.19	F(000) = 359
Triclinic, P1	D_x = 1.560 Mg m⁻³
a = 8.3305 (7) Å	Cu Kα radiation, λ = 1.54184 Å
b = 8.8175 (5) Å	Cell parameters from 3413 reflections
c = 11.5010 (8) Å	θ = 4.1–75.2°
α = 83.096 (6)°	µ = 1.59 mm⁻¹
β = 72.285 (7)°	T = 100 K
γ = 66.328 (7)°	Block, blue
V = 737.02 (10) Å³	0.08 × 0.05 × 0.04 mm

Data collection top

XtaLAB Synergy, Dualflex, HyPix diffractometer	4974 independent reflections
Radiation source: micro-focus sealed X-ray tube	4059 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	R_int = 0.351
ω scans	θ_max = 77.0°, θ_min = 4.0°
Absorption correction: gaussian CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −10→10
T_min = 0.887, T_max = 0.933	k = −11→11
4974 measured reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.058	H-atom parameters constrained
wR(F²) = 0.164	w = 1/[σ²(F_o²) + (0.0938P)² + 0.5989P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
4974 reflections	Δρ_max = 0.63 e Å⁻³
216 parameters	Δρ_min = −0.48 e Å⁻³
0 restraints

Special details top

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

Refinement. Refined as a 2-component twin.

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

	x	y	z	U_iso*/U_eq
Cu1	1.000000	1.000000	0.000000	0.0307 (3)
N1	0.8308 (5)	1.2313 (4)	0.0572 (3)	0.0307 (7)
C2	0.6494 (6)	1.2882 (5)	0.0940 (3)	0.0346 (9)
H2	0.579750	1.223703	0.098581	0.042*
N3	0.5778 (5)	1.4497 (4)	0.1241 (3)	0.0341 (7)
C4	0.7217 (6)	1.4981 (5)	0.1059 (3)	0.0370 (9)
H4	0.713759	1.605240	0.119983	0.044*
C5	0.8768 (6)	1.3634 (5)	0.0640 (3)	0.0356 (9)
H5	0.997586	1.360295	0.042815	0.043*
C6	0.3834 (6)	1.5485 (5)	0.1760 (3)	0.0369 (9)
H6B	0.311128	1.514729	0.137797	0.044*
H6A	0.359413	1.666728	0.156781	0.044*
C7	0.3220 (6)	1.5281 (5)	0.3128 (3)	0.0353 (9)
C8	0.2873 (6)	1.3870 (5)	0.3607 (3)	0.0356 (9)
H8	0.298845	1.306395	0.307527	0.043*
C9	0.2359 (6)	1.3654 (5)	0.4866 (3)	0.0350 (8)
C10	0.2188 (6)	1.4839 (5)	0.5637 (3)	0.0382 (9)
H10	0.182928	1.468793	0.649503	0.046*
C11	0.2533 (6)	1.6249 (5)	0.5175 (4)	0.0374 (9)
C12	0.3045 (6)	1.6446 (5)	0.3914 (3)	0.0358 (9)
H12	0.327981	1.740232	0.358553	0.043*
C13	0.2327 (7)	1.7541 (5)	0.6013 (4)	0.0438 (10)
H13B	0.343213	1.719187	0.628063	0.066*
H13A	0.127065	1.767555	0.672532	0.066*
H13C	0.214230	1.859664	0.557791	0.066*
C14	0.1947 (7)	1.2125 (5)	0.5322 (4)	0.0416 (10)
H14A	0.070245	1.233177	0.528902	0.050*
H14B	0.281645	1.119016	0.476450	0.050*
N15	0.2061 (5)	1.1644 (4)	0.6566 (3)	0.0351 (7)
C16	0.0760 (6)	1.1347 (5)	0.7480 (3)	0.0339 (8)
H16	−0.039130	1.145571	0.741615	0.041*
N17	0.1310 (5)	1.0884 (4)	0.8480 (3)	0.0322 (7)
C18	0.3030 (6)	1.0883 (5)	0.8188 (4)	0.0370 (9)
H18	0.376792	1.060642	0.873035	0.044*
C19	0.3520 (6)	1.1340 (5)	0.7003 (4)	0.0389 (9)
H19	0.464666	1.143016	0.656587	0.047*
N20	0.7419 (5)	0.9334 (4)	−0.1587 (3)	0.0372 (8)
O21	0.7649 (4)	1.0298 (4)	−0.0992 (3)	0.0403 (7)
O22	0.7019 (5)	0.8155 (4)	−0.1065 (3)	0.0467 (8)
O23	0.7579 (5)	0.9587 (4)	−0.2702 (3)	0.0494 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0419 (5)	0.0252 (4)	0.0246 (4)	−0.0160 (3)	−0.0057 (3)	0.0035 (3)
N1	0.0411 (19)	0.0281 (16)	0.0247 (14)	−0.0180 (14)	−0.0062 (13)	0.0026 (11)
C2	0.050 (3)	0.0275 (19)	0.0283 (18)	−0.0196 (18)	−0.0083 (16)	0.0037 (14)
N3	0.044 (2)	0.0311 (17)	0.0262 (15)	−0.0169 (14)	−0.0054 (13)	0.0022 (12)
C4	0.048 (2)	0.031 (2)	0.0342 (19)	−0.0213 (18)	−0.0066 (17)	0.0017 (15)
C5	0.046 (2)	0.0288 (19)	0.036 (2)	−0.0206 (18)	−0.0083 (17)	0.0020 (14)
C6	0.043 (2)	0.033 (2)	0.0301 (19)	−0.0146 (17)	−0.0072 (16)	0.0052 (14)
C7	0.040 (2)	0.032 (2)	0.0289 (18)	−0.0119 (17)	−0.0067 (15)	0.0036 (14)
C8	0.042 (2)	0.034 (2)	0.0309 (19)	−0.0163 (17)	−0.0077 (16)	0.0017 (15)
C9	0.041 (2)	0.035 (2)	0.0300 (19)	−0.0181 (17)	−0.0084 (16)	0.0055 (14)
C10	0.045 (2)	0.040 (2)	0.0283 (18)	−0.0177 (19)	−0.0079 (16)	0.0045 (15)
C11	0.043 (2)	0.033 (2)	0.032 (2)	−0.0123 (17)	−0.0081 (16)	−0.0007 (15)
C12	0.042 (2)	0.029 (2)	0.0336 (19)	−0.0143 (17)	−0.0082 (16)	0.0050 (15)
C13	0.056 (3)	0.038 (2)	0.038 (2)	−0.021 (2)	−0.0113 (19)	0.0005 (17)
C14	0.061 (3)	0.044 (2)	0.0290 (19)	−0.033 (2)	−0.0116 (18)	0.0072 (16)
N15	0.043 (2)	0.0359 (18)	0.0283 (16)	−0.0207 (15)	−0.0072 (13)	0.0043 (12)
C16	0.041 (2)	0.031 (2)	0.0291 (18)	−0.0182 (17)	−0.0050 (16)	0.0051 (14)
N17	0.0399 (19)	0.0280 (16)	0.0271 (15)	−0.0155 (14)	−0.0053 (13)	0.0039 (12)
C18	0.041 (2)	0.034 (2)	0.037 (2)	−0.0178 (18)	−0.0126 (17)	0.0081 (15)
C19	0.039 (2)	0.040 (2)	0.038 (2)	−0.0202 (19)	−0.0069 (17)	0.0050 (16)
N20	0.044 (2)	0.0337 (18)	0.0374 (18)	−0.0185 (15)	−0.0127 (14)	0.0027 (13)
O21	0.0534 (19)	0.0375 (15)	0.0377 (14)	−0.0244 (14)	−0.0138 (13)	−0.0001 (11)
O22	0.060 (2)	0.0386 (16)	0.0534 (18)	−0.0305 (15)	−0.0209 (15)	0.0122 (13)
O23	0.069 (2)	0.0513 (19)	0.0363 (16)	−0.0293 (16)	−0.0204 (14)	0.0063 (13)

Geometric parameters (Å, º) top

Cu1—N1	2.007 (3)	C10—C11	1.395 (6)
Cu1—N1ⁱ	2.007 (3)	C10—H10	0.9500
Cu1—N17ⁱⁱ	2.012 (3)	C11—C12	1.392 (5)
Cu1—N17ⁱⁱⁱ	2.012 (3)	C11—C13	1.503 (6)
N1—C2	1.330 (5)	C12—H12	0.9500
N1—C5	1.381 (5)	C13—H13B	0.9800
C2—N3	1.347 (5)	C13—H13A	0.9800
C2—H2	0.9500	C13—H13C	0.9800
N3—C4	1.379 (5)	C14—N15	1.463 (5)
N3—C6	1.463 (5)	C14—H14A	0.9900
C4—C5	1.357 (6)	C14—H14B	0.9900
C4—H4	0.9500	N15—C16	1.348 (5)
C5—H5	0.9500	N15—C19	1.371 (6)
C6—C7	1.512 (5)	C16—N17	1.325 (5)
C6—H6B	0.9900	C16—H16	0.9500
C6—H6A	0.9900	N17—C18	1.368 (5)
C7—C12	1.385 (6)	C18—C19	1.359 (6)
C7—C8	1.400 (5)	C18—H18	0.9500
C8—C9	1.392 (5)	C19—H19	0.9500
C8—H8	0.9500	N20—O22	1.248 (4)
C9—C10	1.387 (6)	N20—O23	1.250 (4)
C9—C14	1.517 (5)	N20—O21	1.256 (4)

N1—Cu1—N1ⁱ	180.0	C11—C10—H10	119.4
N1—Cu1—N17ⁱⁱ	89.35 (12)	C12—C11—C10	118.2 (4)
N1ⁱ—Cu1—N17ⁱⁱ	90.65 (12)	C12—C11—C13	120.7 (4)
N1—Cu1—N17ⁱⁱⁱ	90.65 (12)	C10—C11—C13	121.1 (4)
N1ⁱ—Cu1—N17ⁱⁱⁱ	89.35 (12)	C7—C12—C11	121.5 (4)
N17ⁱⁱ—Cu1—N17ⁱⁱⁱ	180.00 (17)	C7—C12—H12	119.3
C2—N1—C5	106.2 (3)	C11—C12—H12	119.3
C2—N1—Cu1	126.0 (3)	C11—C13—H13B	109.5
C5—N1—Cu1	127.7 (3)	C11—C13—H13A	109.5
N1—C2—N3	110.8 (4)	H13B—C13—H13A	109.5
N1—C2—H2	124.6	C11—C13—H13C	109.5
N3—C2—H2	124.6	H13B—C13—H13C	109.5
C2—N3—C4	107.2 (3)	H13A—C13—H13C	109.5
C2—N3—C6	125.3 (3)	N15—C14—C9	114.0 (3)
C4—N3—C6	127.3 (3)	N15—C14—H14A	108.8
C5—C4—N3	106.8 (3)	C9—C14—H14A	108.8
C5—C4—H4	126.6	N15—C14—H14B	108.8
N3—C4—H4	126.6	C9—C14—H14B	108.8
C4—C5—N1	109.0 (4)	H14A—C14—H14B	107.6
C4—C5—H5	125.5	C16—N15—C19	107.5 (3)
N1—C5—H5	125.5	C16—N15—C14	125.5 (4)
N3—C6—C7	112.1 (3)	C19—N15—C14	126.9 (3)
N3—C6—H6B	109.2	N17—C16—N15	110.6 (4)
C7—C6—H6B	109.2	N17—C16—H16	124.7
N3—C6—H6A	109.2	N15—C16—H16	124.7
C7—C6—H6A	109.2	C16—N17—C18	106.2 (3)
H6B—C6—H6A	107.9	C16—N17—Cu1^iv	125.1 (3)
C12—C7—C8	119.5 (3)	C18—N17—Cu1^iv	127.9 (2)
C12—C7—C6	120.9 (3)	C19—C18—N17	109.5 (4)
C8—C7—C6	119.5 (4)	C19—C18—H18	125.2
C9—C8—C7	119.7 (4)	N17—C18—H18	125.2
C9—C8—H8	120.2	C18—C19—N15	106.1 (4)
C7—C8—H8	120.2	C18—C19—H19	126.9
C10—C9—C8	119.8 (4)	N15—C19—H19	126.9
C10—C9—C14	123.3 (3)	O22—N20—O23	120.9 (3)
C8—C9—C14	116.9 (4)	O22—N20—O21	120.2 (3)
C9—C10—C11	121.3 (4)	O23—N20—O21	118.9 (3)
C9—C10—H10	119.4

C5—N1—C2—N3	−0.1 (4)	C9—C10—C11—C12	0.4 (7)
Cu1—N1—C2—N3	−178.8 (2)	C9—C10—C11—C13	179.3 (4)
N1—C2—N3—C4	−0.3 (4)	C8—C7—C12—C11	0.1 (7)
N1—C2—N3—C6	−175.6 (3)	C6—C7—C12—C11	−178.1 (4)
C2—N3—C4—C5	0.6 (4)	C10—C11—C12—C7	−0.3 (7)
C6—N3—C4—C5	175.7 (3)	C13—C11—C12—C7	−179.2 (4)
N3—C4—C5—N1	−0.6 (4)	C10—C9—C14—N15	−23.0 (6)
C2—N1—C5—C4	0.4 (4)	C8—C9—C14—N15	159.2 (4)
Cu1—N1—C5—C4	179.1 (3)	C9—C14—N15—C16	128.5 (4)
C2—N3—C6—C7	83.4 (5)	C9—C14—N15—C19	−54.7 (6)
C4—N3—C6—C7	−91.0 (4)	C19—N15—C16—N17	0.5 (4)
N3—C6—C7—C12	99.2 (5)	C14—N15—C16—N17	177.9 (4)
N3—C6—C7—C8	−79.0 (5)	N15—C16—N17—C18	−0.1 (4)
C12—C7—C8—C9	−0.1 (6)	N15—C16—N17—Cu1^iv	−170.8 (2)
C6—C7—C8—C9	178.2 (4)	C16—N17—C18—C19	−0.4 (4)
C7—C8—C9—C10	0.2 (6)	Cu1^iv—N17—C18—C19	170.0 (3)
C7—C8—C9—C14	178.1 (4)	N17—C18—C19—N15	0.7 (4)
C8—C9—C10—C11	−0.4 (7)	C16—N15—C19—C18	−0.8 (4)
C14—C9—C10—C11	−178.2 (4)	C14—N15—C19—C18	−178.0 (4)

Symmetry codes: (i) −x+2, −y+2, −z; (ii) −x+1, −y+2, −z+1; (iii) x+1, y, z−1; (iv) x−1, y, z+1.

(5) top

Crystal data top

C₃₈H₄₈Cu₂N₁₄O₁₃	F(000) = 1072
M_r = 1035.98	D_x = 1.566 Mg m⁻³
Monoclinic, C2/m	Cu Kα radiation, λ = 1.54184 Å
a = 14.5524 (3) Å	Cell parameters from 3348 reflections
b = 18.5525 (4) Å	θ = 3.9–73.2°
c = 8.1383 (1) Å	µ = 1.89 mm⁻¹
β = 90.245 (2)°	T = 100 K
V = 2197.19 (7) Å³	Block, blue
Z = 2	0.29 × 0.08 × 0.04 mm

Data collection top

XtaLAB Synergy, Dualflex, HyPix diffractometer	2131 independent reflections
Radiation source: micro-focus sealed X-ray tube	1931 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	R_int = 0.038
ω scans	θ_max = 76.6°, θ_min = 3.9°
Absorption correction: multi-scan CrysAlisPro 1.171.42.55a (Rigaku Oxford Diffraction, 2022) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −17→16
T_min = 0.691, T_max = 1.000	k = −21→23
5900 measured reflections	l = −5→10

Refinement top

Refinement on F²	3 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.101	w = 1/[σ²(F_o²) + (0.0528P)² + 2.6293P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2131 reflections	Δρ_max = 0.37 e Å⁻³
181 parameters	Δρ_min = −0.46 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cu1	0.500000	0.36027 (2)	0.500000	0.01697 (16)
N1	0.36838 (12)	0.35157 (9)	0.4457 (2)	0.0178 (4)
C2	0.29795 (14)	0.37011 (11)	0.5395 (2)	0.0183 (4)
H2	0.303351	0.392798	0.643758	0.022*
N3	0.21812 (12)	0.35250 (9)	0.4674 (2)	0.0162 (4)
C4	0.23800 (14)	0.32033 (11)	0.3189 (2)	0.0185 (4)
H4	0.195207	0.301853	0.241141	0.022*
C5	0.33095 (14)	0.32038 (11)	0.3062 (2)	0.0200 (4)
H5	0.364879	0.301970	0.215968	0.024*
C6	0.12530 (14)	0.36393 (10)	0.5358 (3)	0.0172 (4)
H6A	0.110084	0.323731	0.610871	0.021*
H6B	0.079634	0.363972	0.445239	0.021*
C7	0.11958 (13)	0.43434 (10)	0.6281 (2)	0.0159 (4)
C8	0.12063 (18)	0.500000	0.5421 (3)	0.0159 (5)
C9	0.1129 (2)	0.500000	0.8825 (3)	0.0194 (6)
H9	0.108658	0.500000	0.998940	0.023*
C10	0.11579 (13)	0.43413 (11)	0.8012 (2)	0.0175 (4)
C11	0.11859 (17)	0.36554 (11)	0.9006 (3)	0.0244 (5)
H11A	0.112738	0.377165	1.017585	0.037*
H11B	0.177102	0.340787	0.881897	0.037*
H11C	0.067741	0.334124	0.867018	0.037*
C12	0.1238 (2)	0.500000	0.3557 (3)	0.0200 (6)
H12A	0.119514	0.450351	0.315237	0.030*	0.5
H12B	0.181773	0.521440	0.319107	0.030*	0.5
H12C	0.072192	0.528208	0.312295	0.030*	0.5
N13	0.44219 (12)	0.30478 (10)	0.7936 (2)	0.0216 (4)
O14	0.46717 (10)	0.36717 (8)	0.73845 (17)	0.0205 (3)
O15	0.46403 (10)	0.25025 (8)	0.71487 (19)	0.0257 (4)
O16	0.39698 (12)	0.30241 (10)	0.92138 (19)	0.0351 (4)
N17	0.3592 (5)	0.500000	0.2543 (7)	0.0367 (14)	0.5
N17A	0.3399 (4)	0.500000	−0.1827 (7)	0.0294 (12)	0.5
C18	0.3615 (7)	0.500000	0.114 (2)	0.021 (2)	0.5
C19	0.3640 (2)	0.500000	−0.0569 (5)	0.0324 (8)
C19A	0.3915 (8)	0.500000	0.121 (2)	0.032 (3)	0.5
H19A	0.408146	0.549032	0.154893	0.048*	0.5
H19B	0.444250	0.467930	0.137341	0.048*	0.5
H19C	0.339884	0.483038	0.188078	0.048*	0.5
O20	0.5240 (3)	0.500000	0.4716 (5)	0.0261 (10)*	0.5
H20A	0.562 (4)	0.500000	0.574 (4)	0.031*	0.5
H20B	0.569 (3)	0.500000	0.382 (5)	0.031*	0.5

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0105 (2)	0.0215 (3)	0.0189 (2)	0.000	0.00054 (16)	0.000
N1	0.0124 (9)	0.0210 (9)	0.0198 (8)	0.0005 (6)	0.0006 (7)	−0.0028 (7)
C2	0.0121 (9)	0.0223 (10)	0.0203 (9)	0.0014 (8)	0.0005 (8)	−0.0018 (8)
N3	0.0113 (8)	0.0178 (8)	0.0194 (8)	0.0004 (6)	0.0028 (6)	−0.0010 (6)
C4	0.0173 (10)	0.0203 (10)	0.0180 (9)	−0.0007 (8)	−0.0002 (7)	−0.0025 (8)
C5	0.0181 (10)	0.0215 (10)	0.0203 (9)	−0.0006 (8)	0.0029 (8)	−0.0029 (8)
C6	0.0103 (9)	0.0187 (10)	0.0227 (9)	−0.0011 (7)	0.0028 (8)	−0.0019 (7)
C7	0.0084 (9)	0.0193 (10)	0.0200 (9)	0.0006 (7)	0.0010 (7)	−0.0011 (7)
C8	0.0078 (12)	0.0217 (14)	0.0182 (12)	0.000	0.0008 (10)	0.000
C9	0.0192 (14)	0.0233 (14)	0.0159 (12)	0.000	0.0007 (11)	0.000
C10	0.0129 (10)	0.0193 (10)	0.0203 (9)	0.0003 (7)	0.0023 (7)	0.0019 (7)
C11	0.0302 (12)	0.0212 (10)	0.0218 (10)	0.0005 (8)	0.0003 (9)	0.0046 (8)
C12	0.0185 (14)	0.0230 (14)	0.0184 (13)	0.000	0.0029 (11)	0.000
N13	0.0132 (8)	0.0308 (10)	0.0207 (8)	−0.0002 (7)	−0.0005 (7)	0.0000 (7)
O14	0.0163 (8)	0.0226 (8)	0.0225 (7)	−0.0010 (6)	0.0011 (6)	−0.0021 (6)
O15	0.0195 (8)	0.0237 (8)	0.0338 (8)	−0.0005 (6)	0.0012 (6)	−0.0032 (6)
O16	0.0317 (9)	0.0511 (11)	0.0225 (7)	−0.0055 (8)	0.0104 (7)	0.0021 (7)
N17	0.048 (4)	0.031 (3)	0.031 (3)	0.000	−0.009 (3)	0.000
N17A	0.031 (3)	0.024 (3)	0.033 (3)	0.000	−0.003 (2)	0.000
C18	0.006 (6)	0.023 (4)	0.034 (5)	0.000	−0.003 (5)	0.000
C19	0.0310 (19)	0.0292 (17)	0.0370 (19)	0.000	−0.0008 (15)	0.000
C19A	0.016 (7)	0.044 (5)	0.037 (5)	0.000	−0.006 (7)	0.000

Geometric parameters (Å, º) top

Cu1—N1	1.9704 (17)	C11—H11B	0.9800
Cu1—N1ⁱ	1.9704 (17)	C11—H11C	0.9800
Cu1—O14ⁱ	2.0045 (14)	C12—H12A	0.9800
Cu1—O14	2.0046 (14)	C12—H12B	0.9800
N1—C2	1.326 (3)	C12—H12C	0.9800
N1—C5	1.384 (3)	C12—H12Aⁱⁱ	0.980 (3)
C2—N3	1.340 (3)	C12—H12Bⁱⁱ	0.980 (17)
C2—H2	0.9500	C12—H12Cⁱⁱ	0.98 (2)
N3—C4	1.379 (2)	N13—O16	1.233 (2)
N3—C6	1.478 (3)	N13—O15	1.240 (2)
C4—C5	1.357 (3)	N13—O14	1.294 (2)
C4—H4	0.9500	N17—C18	1.142 (19)
C5—H5	0.9500	C18—C19	1.392 (19)
C6—C7	1.510 (3)	C19—C19A	1.503 (18)
C6—H6A	0.9900	C19A—H19A	0.9800
C6—H6B	0.9900	C19A—H19B	0.9800
C7—C8	1.405 (2)	C19A—H19C	0.9800
C7—C10	1.410 (3)	C19A—H19Aⁱⁱ	0.980 (11)
C8—C12	1.518 (4)	C19A—H19Bⁱⁱ	0.98 (3)
C9—C10	1.391 (2)	C19A—H19Cⁱⁱ	0.98 (2)
C9—C10ⁱⁱ	1.391 (2)	O20—O20ⁱⁱⁱ	0.840 (8)
C9—H9	0.9500	O20—H20A	0.99 (2)
C10—C11	1.508 (3)	O20—H20B	0.98 (2)
C11—H11A	0.9800

N1—Cu1—N1ⁱ	170.60 (10)	C8—C12—H12A	109.5
N1—Cu1—O14ⁱ	91.36 (7)	C8—C12—H12B	109.5
N1ⁱ—Cu1—O14ⁱ	89.24 (7)	H12A—C12—H12B	109.5
N1—Cu1—O14	89.24 (7)	C8—C12—H12C	109.5
N1ⁱ—Cu1—O14	91.36 (7)	H12A—C12—H12C	109.5
O14ⁱ—Cu1—O14	172.68 (8)	H12B—C12—H12C	109.5
C2—N1—C5	106.16 (17)	C8—C12—H12Aⁱⁱ	109.47 (7)
C2—N1—Cu1	127.07 (14)	H12A—C12—H12Aⁱⁱ	140.1
C5—N1—Cu1	126.65 (14)	H12B—C12—H12Aⁱⁱ	64.6
N1—C2—N3	110.82 (18)	H12C—C12—H12Aⁱⁱ	47.9
N1—C2—H2	124.6	C8—C12—H12Bⁱⁱ	109.5 (4)
N3—C2—H2	124.6	H12A—C12—H12Bⁱⁱ	64.6
C2—N3—C4	107.74 (17)	H12B—C12—H12Bⁱⁱ	47.9
C2—N3—C6	126.30 (17)	H12C—C12—H12Bⁱⁱ	140.1
C4—N3—C6	125.96 (17)	H12Aⁱⁱ—C12—H12Bⁱⁱ	109.5
C5—C4—N3	106.23 (17)	C8—C12—H12Cⁱⁱ	109.5 (4)
C5—C4—H4	126.9	H12A—C12—H12Cⁱⁱ	47.9
N3—C4—H4	126.9	H12B—C12—H12Cⁱⁱ	140.1
C4—C5—N1	109.06 (17)	H12C—C12—H12Cⁱⁱ	64.6
C4—C5—H5	125.5	H12Aⁱⁱ—C12—H12Cⁱⁱ	109.5
N1—C5—H5	125.5	H12Bⁱⁱ—C12—H12Cⁱⁱ	109.5
N3—C6—C7	111.34 (16)	O16—N13—O15	123.05 (18)
N3—C6—H6A	109.4	O16—N13—O14	118.43 (18)
C7—C6—H6A	109.4	O15—N13—O14	118.51 (16)
N3—C6—H6B	109.4	N13—O14—Cu1	110.33 (11)
C7—C6—H6B	109.4	C18—N17—H19Aⁱⁱ	53.9 (8)
H6A—C6—H6B	108.0	N17—C18—C19	179.8 (10)
C8—C7—C10	120.05 (18)	N17—C18—H19Aⁱⁱ	74.8 (19)
C8—C7—C6	120.09 (18)	C19—C18—H19Aⁱⁱ	105 (2)
C10—C7—C6	119.83 (17)	N17—C18—H19Bⁱⁱ	83.7 (17)
C7ⁱⁱ—C8—C7	120.2 (2)	C19—C18—H19Bⁱⁱ	96.5 (17)
C7ⁱⁱ—C8—C12	119.89 (12)	C19—C18—H19Cⁱⁱ	145 (2)
C7—C8—C12	119.89 (12)	N17A—C19—C19A	176.5 (7)
C10—C9—C10ⁱⁱ	123.0 (3)	C19—C19A—H19A	109.5
C10—C9—H9	118.5	C19—C19A—H19B	109.5
C10ⁱⁱ—C9—H9	118.5	H19A—C19A—H19B	109.5
C9—C10—C7	118.32 (18)	C19—C19A—H19C	109.5
C9—C10—C11	119.13 (18)	H19A—C19A—H19C	109.5
C7—C10—C11	122.50 (18)	H19B—C19A—H19C	109.5
C10—C11—H11A	109.5	C19—C19A—H19Aⁱⁱ	109.5 (2)
C10—C11—H11B	109.5	C19—C19A—H19Bⁱⁱ	109.5 (8)
H11A—C11—H11B	109.5	C19—C19A—H19Cⁱⁱ	109.5 (6)
C10—C11—H11C	109.5	O20ⁱⁱⁱ—O20—H20A	90 (3)
H11A—C11—H11C	109.5	O20ⁱⁱⁱ—O20—H20B	165 (3)
H11B—C11—H11C	109.5	H20A—O20—H20B	105 (3)

C5—N1—C2—N3	0.0 (2)	C10—C7—C8—C7ⁱⁱ	1.2 (4)
Cu1—N1—C2—N3	−176.16 (13)	C6—C7—C8—C7ⁱⁱ	−177.07 (15)
N1—C2—N3—C4	0.4 (2)	C10—C7—C8—C12	−179.4 (2)
N1—C2—N3—C6	179.16 (17)	C6—C7—C8—C12	2.4 (3)
C2—N3—C4—C5	−0.6 (2)	C10ⁱⁱ—C9—C10—C7	−1.6 (4)
C6—N3—C4—C5	−179.36 (18)	C10ⁱⁱ—C9—C10—C11	175.97 (19)
N3—C4—C5—N1	0.6 (2)	C8—C7—C10—C9	0.2 (3)
C2—N1—C5—C4	−0.3 (2)	C6—C7—C10—C9	178.4 (2)
Cu1—N1—C5—C4	175.81 (14)	C8—C7—C10—C11	−177.3 (2)
C2—N3—C6—C7	37.6 (3)	C6—C7—C10—C11	0.9 (3)
C4—N3—C6—C7	−143.87 (19)	O16—N13—O14—Cu1	−160.73 (15)
N3—C6—C7—C8	71.4 (2)	O15—N13—O14—Cu1	18.6 (2)
N3—C6—C7—C10	−106.9 (2)

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

(6) top

Crystal data top

C₃₈H₄₈Cu₂N₁₂O₁₂	Z = 1
M_r = 991.96	F(000) = 514
Triclinic, P1	D_x = 1.502 Mg m⁻³
a = 7.6782 (1) Å	Cu Kα radiation, λ = 1.54184 Å
b = 12.1895 (1) Å	Cell parameters from 17873 reflections
c = 12.7801 (1) Å	θ = 3.7–76.2°
α = 68.886 (1)°	µ = 1.83 mm⁻¹
β = 89.049 (1)°	T = 100 K
γ = 79.749 (1)°	Block, blue
V = 1096.55 (2) Å³	0.51 × 0.47 × 0.23 mm

Data collection top

XtaLAB Synergy, Dualflex, HyPix diffractometer	4292 independent reflections
Radiation source: micro-focus sealed X-ray tube	4092 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	R_int = 0.035
ω scans	θ_max = 76.5°, θ_min = 3.7°
Absorption correction: multi-scan CrysAlisPro 1.171.42.55a (Rigaku Oxford Diffraction, 2022) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −9→9
T_min = 0.770, T_max = 1.000	k = −14→15
27783 measured reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.030	H-atom parameters constrained
wR(F²) = 0.078	w = 1/[σ²(F_o²) + (0.031P)² + 1.0102P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
4292 reflections	Δρ_max = 0.29 e Å⁻³
294 parameters	Δρ_min = −0.41 e Å⁻³
0 restraints

Special details top

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

	x	y	z	U_iso*/U_eq
Cu1	0.05239 (3)	0.27265 (2)	0.37040 (2)	0.02074 (9)
N1	0.17786 (19)	0.25917 (13)	0.50842 (12)	0.0218 (3)
C2	0.2676 (2)	0.15915 (16)	0.58450 (14)	0.0208 (3)
N3	0.34506 (19)	0.18552 (13)	0.66403 (11)	0.0208 (3)
C4	0.3048 (2)	0.30809 (16)	0.63655 (15)	0.0251 (4)
H4	0.342519	0.352357	0.676911	0.030*
C5	0.2010 (2)	0.35235 (16)	0.54084 (15)	0.0241 (4)
H5	0.151870	0.434373	0.502091	0.029*
C6	0.2842 (3)	0.03583 (16)	0.58504 (16)	0.0275 (4)
H6A	0.227755	0.038459	0.515764	0.041*
H6B	0.226053	−0.012113	0.649936	0.041*
H6C	0.409915	−0.000344	0.589789	0.041*
C7	0.4722 (2)	0.09847 (16)	0.75388 (14)	0.0238 (4)
H7A	0.588437	0.083253	0.721998	0.029*
H7B	0.429098	0.021772	0.785197	0.029*
C8	0.4941 (2)	0.14522 (15)	0.84630 (14)	0.0215 (3)
C9	0.6363 (2)	0.20283 (15)	0.84869 (14)	0.0225 (4)
C10	0.6504 (2)	0.24761 (15)	0.93479 (14)	0.0228 (4)
C11	0.5244 (2)	0.23519 (16)	1.01695 (15)	0.0242 (4)
C12	0.3861 (2)	0.17683 (15)	1.01235 (14)	0.0233 (4)
H12	0.301625	0.167200	1.068607	0.028*
C13	0.3679 (2)	0.13230 (15)	0.92817 (14)	0.0218 (3)
C14	0.2126 (2)	0.07244 (16)	0.92610 (16)	0.0265 (4)
H14A	0.138488	0.073380	0.989049	0.040*
H14B	0.256210	−0.010500	0.932696	0.040*
H14C	0.142354	0.115587	0.855209	0.040*
C15	0.7682 (2)	0.21711 (17)	0.75729 (15)	0.0281 (4)
H15A	0.831687	0.138065	0.762212	0.042*
H15B	0.853008	0.264468	0.766904	0.042*
H15C	0.705041	0.258047	0.683639	0.042*
C16	0.5313 (3)	0.2836 (2)	1.10996 (17)	0.0347 (4)
H16A	0.430858	0.265856	1.157555	0.052*
H16B	0.525116	0.370379	1.077306	0.052*
H16C	0.642404	0.245916	1.155364	0.052*
C17	0.8002 (2)	0.31173 (16)	0.93841 (15)	0.0257 (4)
H17A	0.806252	0.321042	1.012012	0.031*
H17B	0.913991	0.263452	0.930053	0.031*
N18	0.77339 (19)	0.43104 (13)	0.84739 (12)	0.0216 (3)
C19	0.8996 (2)	0.49800 (16)	0.80925 (14)	0.0219 (3)
N20	0.83206 (19)	0.59688 (13)	0.72264 (12)	0.0216 (3)
C21	0.6570 (2)	0.59192 (16)	0.70548 (15)	0.0227 (4)
H21	0.576220	0.650620	0.649003	0.027*
C22	0.6191 (2)	0.49006 (16)	0.78202 (15)	0.0232 (4)
H22	0.508460	0.464110	0.789465	0.028*
C23	1.0860 (2)	0.46258 (17)	0.85603 (16)	0.0288 (4)
H23A	1.151586	0.526536	0.817226	0.043*
H23B	1.141800	0.388867	0.845238	0.043*
H23C	1.087275	0.449027	0.936418	0.043*
N24	−0.2497 (2)	0.23976 (14)	0.45388 (12)	0.0254 (3)
O25	−0.24621 (17)	0.34851 (12)	0.40091 (12)	0.0307 (3)
O26	−0.10569 (16)	0.16410 (11)	0.46096 (11)	0.0264 (3)
O27	−0.38214 (17)	0.20360 (13)	0.49729 (12)	0.0338 (3)
N28	0.0486 (2)	0.15321 (14)	0.23342 (12)	0.0256 (3)
O29	−0.04706 (17)	0.25118 (11)	0.23515 (11)	0.0276 (3)
O30	0.0037 (2)	0.10883 (13)	0.16824 (11)	0.0359 (3)
O31	0.18280 (18)	0.10975 (13)	0.29853 (11)	0.0328 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.01840 (14)	0.02363 (15)	0.01976 (14)	−0.00611 (10)	−0.00143 (9)	−0.00623 (10)
N1	0.0197 (7)	0.0243 (7)	0.0199 (7)	−0.0046 (6)	−0.0006 (5)	−0.0060 (6)
C2	0.0192 (8)	0.0250 (9)	0.0180 (8)	−0.0069 (7)	0.0021 (6)	−0.0063 (7)
N3	0.0208 (7)	0.0222 (7)	0.0177 (7)	−0.0025 (6)	−0.0018 (5)	−0.0059 (6)
C4	0.0288 (9)	0.0227 (9)	0.0243 (9)	−0.0015 (7)	−0.0022 (7)	−0.0106 (7)
C5	0.0255 (9)	0.0222 (8)	0.0237 (9)	−0.0008 (7)	−0.0020 (7)	−0.0086 (7)
C6	0.0331 (10)	0.0237 (9)	0.0257 (9)	−0.0090 (7)	−0.0030 (7)	−0.0071 (7)
C7	0.0253 (9)	0.0230 (9)	0.0208 (8)	0.0000 (7)	−0.0059 (7)	−0.0070 (7)
C8	0.0237 (8)	0.0185 (8)	0.0189 (8)	−0.0003 (7)	−0.0049 (6)	−0.0040 (7)
C9	0.0234 (8)	0.0196 (8)	0.0196 (8)	−0.0008 (7)	−0.0030 (7)	−0.0027 (7)
C10	0.0237 (8)	0.0189 (8)	0.0226 (8)	−0.0038 (7)	−0.0041 (7)	−0.0036 (7)
C11	0.0268 (9)	0.0214 (8)	0.0222 (8)	−0.0018 (7)	−0.0032 (7)	−0.0064 (7)
C12	0.0239 (8)	0.0226 (8)	0.0202 (8)	−0.0024 (7)	−0.0002 (7)	−0.0048 (7)
C13	0.0224 (8)	0.0178 (8)	0.0209 (8)	−0.0013 (7)	−0.0043 (7)	−0.0027 (7)
C14	0.0244 (9)	0.0257 (9)	0.0277 (9)	−0.0049 (7)	−0.0024 (7)	−0.0074 (7)
C15	0.0260 (9)	0.0318 (10)	0.0253 (9)	−0.0056 (8)	0.0009 (7)	−0.0089 (8)
C16	0.0370 (11)	0.0431 (12)	0.0320 (10)	−0.0118 (9)	0.0028 (8)	−0.0212 (9)
C17	0.0277 (9)	0.0226 (9)	0.0232 (9)	−0.0063 (7)	−0.0037 (7)	−0.0031 (7)
N18	0.0216 (7)	0.0217 (7)	0.0200 (7)	−0.0049 (6)	−0.0014 (6)	−0.0052 (6)
C19	0.0210 (8)	0.0246 (9)	0.0206 (8)	−0.0052 (7)	0.0003 (6)	−0.0084 (7)
N20	0.0200 (7)	0.0245 (7)	0.0200 (7)	−0.0055 (6)	−0.0014 (5)	−0.0071 (6)
C21	0.0187 (8)	0.0251 (9)	0.0237 (8)	−0.0034 (7)	−0.0015 (7)	−0.0085 (7)
C22	0.0189 (8)	0.0250 (9)	0.0251 (9)	−0.0044 (7)	−0.0024 (7)	−0.0081 (7)
C23	0.0226 (9)	0.0295 (10)	0.0300 (10)	−0.0057 (7)	−0.0044 (7)	−0.0051 (8)
N24	0.0216 (7)	0.0312 (8)	0.0232 (7)	−0.0068 (6)	−0.0002 (6)	−0.0088 (6)
O25	0.0261 (7)	0.0271 (7)	0.0362 (7)	−0.0052 (5)	0.0018 (5)	−0.0081 (6)
O26	0.0186 (6)	0.0272 (6)	0.0315 (7)	−0.0045 (5)	0.0000 (5)	−0.0080 (5)
O27	0.0224 (6)	0.0422 (8)	0.0333 (7)	−0.0103 (6)	0.0072 (5)	−0.0077 (6)
N28	0.0275 (8)	0.0294 (8)	0.0212 (7)	−0.0110 (6)	0.0052 (6)	−0.0082 (6)
O29	0.0265 (6)	0.0290 (7)	0.0290 (7)	−0.0047 (5)	−0.0040 (5)	−0.0124 (5)
O30	0.0485 (9)	0.0386 (8)	0.0287 (7)	−0.0150 (7)	0.0023 (6)	−0.0187 (6)
O31	0.0292 (7)	0.0368 (8)	0.0296 (7)	−0.0001 (6)	−0.0026 (6)	−0.0114 (6)

Geometric parameters (Å, º) top

Cu1—N20ⁱ	1.9583 (14)	C13—C14	1.509 (2)
Cu1—N1	1.9642 (14)	C14—H14A	0.9800
Cu1—O26	1.9963 (13)	C14—H14B	0.9800
Cu1—O29	2.0200 (13)	C14—H14C	0.9800
Cu1—O25	2.3957 (13)	C15—H15A	0.9800
N1—C2	1.333 (2)	C15—H15B	0.9800
N1—C5	1.381 (2)	C15—H15C	0.9800
C2—N3	1.347 (2)	C16—H16A	0.9800
C2—C6	1.483 (2)	C16—H16B	0.9800
N3—C4	1.383 (2)	C16—H16C	0.9800
N3—C7	1.479 (2)	C17—N18	1.481 (2)
C4—C5	1.351 (2)	C17—H17A	0.9900
C4—H4	0.9500	C17—H17B	0.9900
C5—H5	0.9500	N18—C19	1.350 (2)
C6—H6A	0.9800	N18—C22	1.384 (2)
C6—H6B	0.9800	C19—N20	1.335 (2)
C6—H6C	0.9800	C19—C23	1.488 (2)
C7—C8	1.508 (2)	N20—C21	1.381 (2)
C7—H7A	0.9900	C21—C22	1.352 (3)
C7—H7B	0.9900	C21—H21	0.9500
C8—C13	1.400 (2)	C22—H22	0.9500
C8—C9	1.405 (2)	C23—H23A	0.9800
C9—C10	1.407 (2)	C23—H23B	0.9800
C9—C15	1.516 (2)	C23—H23C	0.9800
C10—C11	1.402 (3)	N24—O27	1.225 (2)
C10—C17	1.511 (2)	N24—O25	1.258 (2)
C11—C12	1.392 (3)	N24—O26	1.289 (2)
C11—C16	1.511 (3)	N28—O30	1.227 (2)
C12—C13	1.387 (2)	N28—O31	1.245 (2)
C12—H12	0.9500	N28—O29	1.293 (2)

N20ⁱ—Cu1—N1	92.52 (6)	C13—C14—H14A	109.5
N20ⁱ—Cu1—O26	169.11 (6)	C13—C14—H14B	109.5
N1—Cu1—O26	90.41 (6)	H14A—C14—H14B	109.5
N20ⁱ—Cu1—O29	92.67 (6)	C13—C14—H14C	109.5
N1—Cu1—O29	167.82 (6)	H14A—C14—H14C	109.5
O26—Cu1—O29	86.53 (5)	H14B—C14—H14C	109.5
N20ⁱ—Cu1—O25	110.61 (5)	C9—C15—H15A	109.5
N1—Cu1—O25	101.57 (5)	C9—C15—H15B	109.5
O26—Cu1—O25	58.51 (5)	H15A—C15—H15B	109.5
O29—Cu1—O25	86.87 (5)	C9—C15—H15C	109.5
C2—N1—C5	106.91 (14)	H15A—C15—H15C	109.5
C2—N1—Cu1	126.41 (12)	H15B—C15—H15C	109.5
C5—N1—Cu1	126.52 (12)	C11—C16—H16A	109.5
N1—C2—N3	109.67 (15)	C11—C16—H16B	109.5
N1—C2—C6	126.94 (16)	H16A—C16—H16B	109.5
N3—C2—C6	123.39 (15)	C11—C16—H16C	109.5
C2—N3—C4	108.06 (14)	H16A—C16—H16C	109.5
C2—N3—C7	124.30 (14)	H16B—C16—H16C	109.5
C4—N3—C7	127.03 (15)	N18—C17—C10	110.65 (14)
C5—C4—N3	106.32 (15)	N18—C17—H17A	109.5
C5—C4—H4	126.8	C10—C17—H17A	109.5
N3—C4—H4	126.8	N18—C17—H17B	109.5
C4—C5—N1	109.04 (16)	C10—C17—H17B	109.5
C4—C5—H5	125.5	H17A—C17—H17B	108.1
N1—C5—H5	125.5	C19—N18—C22	107.99 (14)
C2—C6—H6A	109.5	C19—N18—C17	125.51 (15)
C2—C6—H6B	109.5	C22—N18—C17	126.39 (15)
H6A—C6—H6B	109.5	N20—C19—N18	109.55 (15)
C2—C6—H6C	109.5	N20—C19—C23	126.32 (16)
H6A—C6—H6C	109.5	N18—C19—C23	124.09 (16)
H6B—C6—H6C	109.5	C19—N20—C21	107.01 (14)
N3—C7—C8	110.73 (14)	C19—N20—Cu1ⁱ	129.43 (12)
N3—C7—H7A	109.5	C21—N20—Cu1ⁱ	123.55 (12)
C8—C7—H7A	109.5	C22—C21—N20	109.00 (15)
N3—C7—H7B	109.5	C22—C21—H21	125.5
C8—C7—H7B	109.5	N20—C21—H21	125.5
H7A—C7—H7B	108.1	C21—C22—N18	106.45 (15)
C13—C8—C9	120.78 (16)	C21—C22—H22	126.8
C13—C8—C7	118.63 (16)	N18—C22—H22	126.8
C9—C8—C7	120.58 (16)	C19—C23—H23A	109.5
C8—C9—C10	119.03 (16)	C19—C23—H23B	109.5
C8—C9—C15	119.17 (16)	H23A—C23—H23B	109.5
C10—C9—C15	121.80 (16)	C19—C23—H23C	109.5
C11—C10—C9	120.53 (16)	H23A—C23—H23C	109.5
C11—C10—C17	119.27 (16)	H23B—C23—H23C	109.5
C9—C10—C17	120.19 (16)	O27—N24—O25	123.24 (15)
C12—C11—C10	118.82 (16)	O27—N24—O26	119.50 (15)
C12—C11—C16	118.47 (17)	O25—N24—O26	117.26 (14)
C10—C11—C16	122.71 (17)	N24—O25—Cu1	83.30 (9)
C13—C12—C11	122.06 (17)	N24—O26—Cu1	100.89 (10)
C13—C12—H12	119.0	O30—N28—O31	123.81 (16)
C11—C12—H12	119.0	O30—N28—O29	118.87 (15)
C12—C13—C8	118.77 (16)	O31—N28—O29	117.31 (15)
C12—C13—C14	119.60 (16)	N28—O29—Cu1	104.24 (10)
C8—C13—C14	121.62 (16)

C5—N1—C2—N3	0.53 (19)	C16—C11—C12—C13	178.47 (17)
Cu1—N1—C2—N3	176.17 (11)	C11—C12—C13—C8	0.9 (3)
C5—N1—C2—C6	−179.27 (17)	C11—C12—C13—C14	−178.54 (16)
Cu1—N1—C2—C6	−3.6 (3)	C9—C8—C13—C12	−0.4 (2)
N1—C2—N3—C4	−0.83 (19)	C7—C8—C13—C12	−179.03 (15)
C6—C2—N3—C4	178.98 (16)	C9—C8—C13—C14	179.03 (15)
N1—C2—N3—C7	−172.39 (15)	C7—C8—C13—C14	0.4 (2)
C6—C2—N3—C7	7.4 (3)	C11—C10—C17—N18	−107.18 (18)
C2—N3—C4—C5	0.8 (2)	C9—C10—C17—N18	71.7 (2)
C7—N3—C4—C5	172.05 (16)	C10—C17—N18—C19	−162.49 (16)
N3—C4—C5—N1	−0.5 (2)	C10—C17—N18—C22	13.2 (2)
C2—N1—C5—C4	0.0 (2)	C22—N18—C19—N20	0.03 (19)
Cu1—N1—C5—C4	−175.65 (12)	C17—N18—C19—N20	176.36 (15)
C2—N3—C7—C8	−164.04 (15)	C22—N18—C19—C23	−178.12 (17)
C4—N3—C7—C8	26.0 (2)	C17—N18—C19—C23	−1.8 (3)
N3—C7—C8—C13	81.88 (19)	N18—C19—N20—C21	−0.10 (19)
N3—C7—C8—C9	−96.77 (18)	C23—C19—N20—C21	178.01 (17)
C13—C8—C9—C10	0.0 (2)	N18—C19—N20—Cu1ⁱ	−178.68 (11)
C7—C8—C9—C10	178.63 (15)	C23—C19—N20—Cu1ⁱ	−0.6 (3)
C13—C8—C9—C15	−178.84 (15)	C19—N20—C21—C22	0.1 (2)
C7—C8—C9—C15	−0.2 (2)	Cu1ⁱ—N20—C21—C22	178.81 (12)
C8—C9—C10—C11	−0.1 (2)	N20—C21—C22—N18	−0.1 (2)
C15—C9—C10—C11	178.71 (16)	C19—N18—C22—C21	0.05 (19)
C8—C9—C10—C17	−179.02 (15)	C17—N18—C22—C21	−176.24 (16)
C15—C9—C10—C17	−0.2 (2)	O27—N24—O25—Cu1	−177.56 (16)
C9—C10—C11—C12	0.6 (3)	O26—N24—O25—Cu1	1.82 (14)
C17—C10—C11—C12	179.50 (15)	O27—N24—O26—Cu1	177.19 (13)
C9—C10—C11—C16	−178.85 (17)	O25—N24—O26—Cu1	−2.20 (16)
C17—C10—C11—C16	0.1 (3)	O30—N28—O29—Cu1	170.58 (12)
C10—C11—C12—C13	−1.0 (3)	O31—N28—O29—Cu1	−9.79 (17)

Symmetry code: (i) −x+1, −y+1, −z+1.

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