2-Dipentyl­amino-4-(4-methoxy­benzyl­idene)-1-phenyl-1H-imidazol-5(4H)-one

Bai, Y.-Q.; Bao, F.; Liu, Y.; Ma, R.; Song, Z.-Y.

doi:10.1107/S1600536807030668

2-Dipentylamino-4-(4-methoxybenzylidene)-1-phenyl-1H-imidazol-5(4H)-one

R. Ma, Z.-Y. Song, Y. Liu, Y.-Q. Bai and F. Bao

In the title compound, C₂₇H₃₅N₃O₂, one of the pentyl side chains is ordered and the other is highly disordered [the occupancies for the major and minor components are 0.52 (1) and 0.48 (1), respectively]. The dihedral angles between the mean planes of the central C₃N₂ ring and the pendant phenyl and methoxybenzene rings are 88.30 (17) and 9.08 (17)°, respectively. A weak intramolecular C—H

N interaction may help to establish the near planarity of the central and methoxybenzene rings.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807030668/hb2457sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807030668/hb2457Isup2.hkl Contains datablock I

CCDC reference: 655055

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Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R factor = 0.063
wR factor = 0.183
Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         36 Perc.
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C20
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for       C21'

Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        200 Deg.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.32 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.74 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C14
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C12
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C19
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C18'
PLAT301_ALERT_3_C Main Residue  Disorder .........................      14.00 Perc.
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C12    -C17           1.36 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C25    -   C26    ...       1.43 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      43.80 Deg.
              C18  -N3   -C18'    1.555   1.555   1.555

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         83

   0 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
  12 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  10 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level G
PUBL013_ALERT_1_G The _publ_section_comment (discussion of study) is
            missing. This is required for a full paper submission (but is
            optional for an electronic paper).

   0 ALERT level A = Data missing that is essential or data in wrong format
   1 ALERT level G = General alerts. Data that may be required is missing

Related literature top

For a related structure, see: Sun et al. (2006). For the synthesis, see: Ding et al. (2001).

Experimental top

The compound was synthesized according to a reported procedure (Ding et al., 2001) and yellow blocks of (I) were grown from a dichloromethane/ diethyl ether solution (1:1 v/v) in about 75% yield. Analysis calculated for C₂₇H₃₅N₃O₂: C 74.79, H 8.14, N 9.69%; found: C 74.85, H 8.36, N 9.79%.

Structure description top

For a related structure, see: Sun et al. (2006). For the synthesis, see: Ding et al. (2001).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Figures top

Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level. H atoms are drawn as spheres of arbitrary radius.

2-Dipentylamino-4-(4-methoxybenzylidene)-1-phenyl-1H-imidazol-5(4H)-one top

Crystal data top

C₂₇H₃₅N₃O₂	Z = 2
M_r = 433.58	F(000) = 468
Triclinic, P1	D_x = 1.150 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4091 (8) Å	Cell parameters from 1232 reflections
b = 11.4405 (9) Å	θ = 2.6–19.1°
c = 11.9354 (10) Å	µ = 0.07 mm⁻¹
α = 90.080 (2)°	T = 292 K
β = 94.746 (2)°	Block, yellow
γ = 102.044 (2)°	0.20 × 0.10 × 0.10 mm
V = 1251.96 (18) Å³

Data collection top

Bruker SMART CCD diffractometer	1734 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.085
Graphite monochromator	θ_max = 26.0°, θ_min = 1.7°
ω scans	h = −11→11
10980 measured reflections	k = −14→14
4871 independent reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.183	H-atom parameters constrained
S = 0.82	w = 1/[σ²(F_o²) + (0.0792P)²] where P = (F_o² + 2F_c²)/3
4871 reflections	(Δ/σ)_max = 0.001
339 parameters	Δρ_max = 0.19 e Å⁻³
83 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₇H₃₅N₃O₂	γ = 102.044 (2)°
M_r = 433.58	V = 1251.96 (18) Å³
Triclinic, P1	Z = 2
a = 9.4091 (8) Å	Mo Kα radiation
b = 11.4405 (9) Å	µ = 0.07 mm⁻¹
c = 11.9354 (10) Å	T = 292 K
α = 90.080 (2)°	0.20 × 0.10 × 0.10 mm
β = 94.746 (2)°

Data collection top

Bruker SMART CCD diffractometer	1734 reflections with I > 2σ(I)
10980 measured reflections	R_int = 0.085
4871 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	83 restraints
wR(F²) = 0.183	H-atom parameters constrained
S = 0.82	Δρ_max = 0.19 e Å⁻³
4871 reflections	Δρ_min = −0.16 e Å⁻³
339 parameters

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)
C1	0.3373 (4)	−0.0641 (3)	0.0797 (3)	0.1419 (15)
H1A	0.4238	−0.0957	0.0775	0.213*
H1B	0.2829	−0.0752	0.0075	0.213*
H1C	0.2784	−0.1050	0.1354	0.213*
C2	0.4595 (4)	0.0944 (3)	0.2069 (3)	0.0871 (9)
C3	0.5044 (4)	0.0181 (3)	0.2825 (3)	0.0984 (10)
H3	0.4800	−0.0639	0.2682	0.118*
C4	0.4948 (3)	0.2159 (3)	0.2300 (3)	0.0904 (9)
H4	0.4625	0.2683	0.1792	0.108*
C5	0.5858 (4)	0.0625 (3)	0.3799 (3)	0.0947 (10)
H5	0.6155	0.0090	0.4308	0.114*
C6	0.5773 (3)	0.2601 (2)	0.3273 (3)	0.0832 (9)
H6	0.6012	0.3422	0.3410	0.100*
C7	0.6254 (3)	0.1840 (2)	0.4055 (2)	0.0731 (8)
C8	0.7086 (3)	0.2258 (3)	0.5116 (2)	0.0807 (8)
H8	0.7259	0.1663	0.5607	0.097*
C9	0.7640 (3)	0.3391 (3)	0.5486 (2)	0.0752 (8)
C10	0.8344 (3)	0.3676 (3)	0.6628 (3)	0.0859 (9)
C11	0.8180 (3)	0.5311 (3)	0.5639 (2)	0.0794 (8)
C12	0.9303 (4)	0.5560 (2)	0.7692 (2)	0.0768 (8)
C13	0.8467 (4)	0.5797 (3)	0.8493 (3)	0.1260 (14)
H13	0.7455	0.5582	0.8379	0.151*
C14	0.9134 (6)	0.6367 (4)	0.9495 (3)	0.1468 (18)
H14	0.8568	0.6538	1.0052	0.176*
C15	1.0587 (7)	0.6665 (3)	0.9650 (3)	0.1258 (15)
H15	1.1035	0.7024	1.0325	0.151*
C16	1.1403 (5)	0.6449 (3)	0.8832 (4)	0.1293 (14)
H16	1.2412	0.6694	0.8933	0.155*
C17	1.0779 (4)	0.5880 (3)	0.7863 (3)	0.1041 (11)
H17	1.1359	0.5708	0.7317	0.125*
C18'	0.8293 (7)	0.7435 (5)	0.6198 (5)	0.087 (2)	0.48
H18C	0.8159	0.7106	0.6939	0.104*	0.48
H18D	0.7496	0.7828	0.5982	0.104*	0.48
C19'	0.9726 (10)	0.8314 (6)	0.6210 (8)	0.125 (3)	0.48
H19C	1.0468	0.7937	0.6578	0.150*	0.48
H19D	0.9954	0.8440	0.5436	0.150*	0.48
C20'	0.9882 (14)	0.9510 (7)	0.6752 (8)	0.138 (4)	0.48
H20C	1.0740	1.0027	0.6492	0.165*	0.48
H20D	0.9047	0.9834	0.6476	0.165*	0.48
C21'	1.0005 (15)	0.9595 (9)	0.7999 (6)	0.179 (6)	0.48
H21C	1.0571	0.9026	0.8288	0.215*	0.48
H21D	0.9035	0.9350	0.8251	0.215*	0.48
C22'	1.0690 (16)	1.0806 (11)	0.8523 (10)	0.127 (5)	0.48
H22D	1.0833	1.0734	0.9324	0.191*	0.48
H22E	1.0059	1.1352	0.8350	0.191*	0.48
H22F	1.1614	1.1100	0.8228	0.191*	0.48
C18	0.9372 (8)	0.7502 (5)	0.5874 (6)	0.098 (2)	0.52
H18A	0.9942	0.7232	0.6497	0.118*	0.52
H18B	1.0036	0.7828	0.5318	0.118*	0.52
C19	0.8732 (10)	0.8431 (6)	0.6270 (8)	0.123 (3)	0.52
H19A	0.8397	0.8795	0.5592	0.148*	0.52
H19B	0.7857	0.8015	0.6590	0.148*	0.52
C20	0.9297 (13)	0.9400 (13)	0.7014 (16)	0.240 (10)	0.52
H20A	0.9033	1.0073	0.6617	0.288*	0.52
H20B	0.8665	0.9254	0.7623	0.288*	0.52
C21	1.0651 (13)	0.9887 (14)	0.7559 (12)	0.208 (6)	0.52
H21A	1.1263	1.0165	0.6957	0.249*	0.52
H21B	1.0999	0.9205	0.7870	0.249*	0.52
C22	1.108 (2)	1.0790 (17)	0.8408 (15)	0.242 (10)	0.52
H22A	1.1578	1.1512	0.8086	0.363*	0.52
H22B	1.1710	1.0534	0.8985	0.363*	0.52
H22C	1.0224	1.0937	0.8729	0.363*	0.52
C23	0.7827 (4)	0.6700 (3)	0.4173 (3)	0.1040 (11)
H23A	0.8301	0.7500	0.3974	0.125*
H23B	0.8116	0.6138	0.3674	0.125*
C24	0.6236 (4)	0.6580 (3)	0.4021 (3)	0.1162 (12)
H24A	0.5943	0.7109	0.4553	0.139*
H24B	0.5764	0.5767	0.4180	0.139*
C25	0.5719 (4)	0.6892 (4)	0.2796 (3)	0.1317 (13)
H25A	0.4689	0.6902	0.2780	0.158*
H25B	0.6225	0.7701	0.2653	0.158*
C26	0.5905 (5)	0.6148 (4)	0.1874 (4)	0.1422 (14)
H26A	0.5425	0.5329	0.2005	0.171*
H26B	0.6937	0.6168	0.1839	0.171*
C27	0.5287 (5)	0.6542 (4)	0.0760 (3)	0.1611 (17)
H27A	0.4270	0.6538	0.0796	0.242*
H27B	0.5400	0.6004	0.0173	0.242*
H27C	0.5798	0.7335	0.0606	0.242*
N1	0.7605 (3)	0.4446 (2)	0.49258 (18)	0.0801 (7)
N2	0.8658 (3)	0.4919 (2)	0.66852 (19)	0.0875 (7)
N3	0.8318 (3)	0.6467 (2)	0.5371 (2)	0.0950 (8)
O1	0.3769 (3)	0.06040 (19)	0.10780 (19)	0.1136 (8)
O2	0.8609 (3)	0.30362 (19)	0.73927 (19)	0.1186 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.166 (4)	0.101 (3)	0.138 (3)	−0.005 (3)	−0.017 (3)	−0.050 (2)
C2	0.091 (2)	0.080 (2)	0.087 (2)	0.0093 (19)	0.0058 (19)	−0.0139 (19)
C3	0.111 (3)	0.070 (2)	0.110 (3)	0.0121 (19)	0.002 (2)	−0.021 (2)
C4	0.107 (3)	0.081 (2)	0.079 (2)	0.0159 (18)	−0.0001 (19)	−0.0028 (16)
C5	0.111 (3)	0.069 (2)	0.105 (3)	0.0264 (18)	0.000 (2)	−0.0029 (17)
C6	0.101 (2)	0.0652 (18)	0.079 (2)	0.0088 (17)	0.0034 (18)	−0.0037 (16)
C7	0.078 (2)	0.0677 (18)	0.074 (2)	0.0152 (16)	0.0118 (16)	−0.0046 (15)
C8	0.095 (2)	0.076 (2)	0.0747 (19)	0.0267 (17)	0.0086 (17)	0.0047 (15)
C9	0.085 (2)	0.074 (2)	0.0669 (18)	0.0194 (16)	0.0024 (16)	−0.0043 (15)
C10	0.103 (2)	0.080 (2)	0.073 (2)	0.0230 (19)	−0.0073 (18)	−0.0016 (17)
C11	0.102 (2)	0.070 (2)	0.0651 (19)	0.0179 (17)	−0.0036 (17)	−0.0034 (16)
C12	0.080 (2)	0.083 (2)	0.0642 (19)	0.0133 (18)	−0.0056 (17)	−0.0074 (15)
C13	0.098 (3)	0.143 (3)	0.128 (3)	−0.005 (2)	0.032 (3)	−0.053 (3)
C14	0.182 (5)	0.133 (3)	0.109 (3)	−0.027 (3)	0.066 (3)	−0.044 (3)
C15	0.174 (5)	0.110 (3)	0.071 (3)	−0.011 (3)	−0.018 (3)	−0.005 (2)
C16	0.115 (3)	0.141 (3)	0.123 (4)	0.021 (3)	−0.028 (3)	−0.028 (3)
C17	0.091 (3)	0.113 (3)	0.104 (3)	0.016 (2)	−0.002 (2)	−0.030 (2)
C18'	0.096 (5)	0.085 (5)	0.083 (4)	0.027 (4)	0.006 (4)	−0.003 (4)
C19'	0.132 (7)	0.102 (6)	0.139 (7)	0.024 (6)	0.000 (6)	−0.019 (5)
C20'	0.140 (7)	0.104 (6)	0.147 (7)	−0.014 (5)	−0.015 (6)	−0.067 (5)
C21'	0.149 (10)	0.233 (14)	0.144 (11)	0.007 (10)	0.032 (9)	0.084 (11)
C22'	0.146 (9)	0.113 (8)	0.106 (7)	0.003 (7)	−0.023 (6)	−0.074 (7)
C18	0.118 (6)	0.084 (4)	0.085 (4)	0.005 (4)	0.006 (4)	−0.008 (4)
C19	0.149 (7)	0.081 (5)	0.133 (6)	0.008 (5)	0.021 (5)	−0.049 (4)
C20	0.209 (12)	0.205 (13)	0.206 (13)	0.041 (8)	0.050 (9)	−0.004 (9)
C21	0.229 (10)	0.221 (10)	0.167 (9)	0.020 (8)	0.049 (8)	−0.038 (8)
C22	0.228 (16)	0.228 (15)	0.253 (16)	−0.017 (11)	0.079 (12)	0.059 (12)
C23	0.129 (3)	0.075 (2)	0.106 (3)	0.016 (2)	0.016 (2)	0.0037 (17)
C24	0.108 (3)	0.117 (3)	0.128 (3)	0.035 (2)	0.008 (3)	0.005 (2)
C25	0.130 (3)	0.153 (4)	0.119 (3)	0.050 (3)	−0.003 (3)	0.021 (3)
C26	0.168 (4)	0.136 (3)	0.123 (3)	0.041 (3)	−0.012 (3)	−0.014 (3)
C27	0.207 (5)	0.170 (4)	0.098 (3)	0.040 (3)	−0.040 (3)	0.008 (3)
N1	0.1053 (19)	0.0673 (15)	0.0648 (14)	0.0161 (13)	−0.0039 (13)	−0.0020 (13)
N2	0.113 (2)	0.0755 (17)	0.0702 (16)	0.0211 (14)	−0.0194 (14)	−0.0090 (13)
N3	0.136 (2)	0.0739 (18)	0.0695 (17)	0.0192 (16)	−0.0171 (15)	−0.0067 (13)
O1	0.1251 (19)	0.1029 (17)	0.1018 (17)	0.0084 (14)	−0.0134 (14)	−0.0250 (13)
O2	0.169 (2)	0.0942 (16)	0.0889 (16)	0.0336 (15)	−0.0292 (15)	0.0069 (13)

Geometric parameters (Å, º) top

C1—O1	1.427 (3)	C19'—H19D	0.9700
C1—H1A	0.9600	C20'—C21'	1.485 (8)
C1—H1B	0.9600	C20'—H20C	0.9700
C1—H1C	0.9600	C20'—H20D	0.9700
C2—C3	1.359 (4)	C21'—C22'	1.511 (8)
C2—O1	1.370 (3)	C21'—H21C	0.9700
C2—C4	1.382 (4)	C21'—H21D	0.9700
C3—C5	1.373 (4)	C22'—H22D	0.9600
C3—H3	0.9300	C22'—H22E	0.9600
C4—C6	1.376 (4)	C22'—H22F	0.9600
C4—H4	0.9300	C18—C19	1.424 (7)
C5—C7	1.389 (4)	C18—N3	1.469 (6)
C5—H5	0.9300	C18—H18A	0.9700
C6—C7	1.389 (4)	C18—H18B	0.9700
C6—H6	0.9300	C19—C20	1.404 (6)
C7—C8	1.457 (4)	C19—H19A	0.9700
C8—C9	1.351 (3)	C19—H19B	0.9700
C8—H8	0.9300	C20—C21	1.387 (8)
C9—N1	1.385 (3)	C20—H20A	0.9700
C9—C10	1.470 (4)	C20—H20B	0.9700
C10—O2	1.213 (3)	C21—C22	1.419 (8)
C10—N2	1.392 (3)	C21—H21A	0.9700
C11—N1	1.302 (3)	C21—H21B	0.9700
C11—N3	1.343 (3)	C22—H22A	0.9600
C11—N2	1.398 (3)	C22—H22B	0.9600
C12—C13	1.348 (4)	C22—H22C	0.9600
C12—C17	1.359 (4)	C23—C24	1.471 (4)
C12—N2	1.429 (3)	C23—N3	1.508 (4)
C13—C14	1.398 (5)	C23—H23A	0.9700
C13—H13	0.9300	C23—H23B	0.9700
C14—C15	1.336 (5)	C24—C25	1.569 (5)
C14—H14	0.9300	C24—H24A	0.9700
C15—C16	1.344 (5)	C24—H24B	0.9700
C15—H15	0.9300	C25—C26	1.434 (5)
C16—C17	1.353 (4)	C25—H25A	0.9700
C16—H16	0.9300	C25—H25B	0.9700
C17—H17	0.9300	C26—C27	1.515 (5)
C18'—N3	1.488 (6)	C26—H26A	0.9700
C18'—C19'	1.503 (7)	C26—H26B	0.9700
C18'—H18C	0.9700	C27—H27A	0.9600
C18'—H18D	0.9700	C27—H27B	0.9600
C19'—C20'	1.487 (7)	C27—H27C	0.9600
C19'—H19C	0.9700

O1—C1—H1A	109.5	C20'—C21'—H21D	108.1
O1—C1—H1B	109.5	C22'—C21'—H21D	108.1
H1A—C1—H1B	109.5	H21C—C21'—H21D	107.3
O1—C1—H1C	109.5	C21'—C22'—H22D	109.5
H1A—C1—H1C	109.5	C21'—C22'—H22E	109.5
H1B—C1—H1C	109.5	H22D—C22'—H22E	109.5
C3—C2—O1	124.9 (3)	C21'—C22'—H22F	109.5
C3—C2—C4	119.4 (3)	H22D—C22'—H22F	109.5
O1—C2—C4	115.7 (3)	H22E—C22'—H22F	109.5
C2—C3—C5	119.8 (3)	C19—C18—N3	114.4 (6)
C2—C3—H3	120.1	C19—C18—H18A	108.7
C5—C3—H3	120.1	N3—C18—H18A	108.7
C6—C4—C2	120.6 (3)	C19—C18—H18B	108.7
C6—C4—H4	119.7	N3—C18—H18B	108.7
C2—C4—H4	119.7	H18A—C18—H18B	107.6
C3—C5—C7	122.6 (3)	C20—C19—C18	131.3 (7)
C3—C5—H5	118.7	C20—C19—H19A	104.4
C7—C5—H5	118.7	C18—C19—H19A	104.4
C4—C6—C7	121.1 (3)	C20—C19—H19B	104.4
C4—C6—H6	119.5	C18—C19—H19B	104.4
C7—C6—H6	119.5	H19A—C19—H19B	105.6
C6—C7—C5	116.5 (3)	C21—C20—C19	135.7 (9)
C6—C7—C8	123.3 (3)	C21—C20—H20A	103.3
C5—C7—C8	120.2 (3)	C19—C20—H20A	103.3
C9—C8—C7	128.9 (3)	C21—C20—H20B	103.3
C9—C8—H8	115.5	C19—C20—H20B	103.3
C7—C8—H8	115.5	H20A—C20—H20B	105.2
C8—C9—N1	128.3 (3)	C20—C21—C22	131.1 (12)
C8—C9—C10	122.5 (3)	C20—C21—H21A	104.5
N1—C9—C10	109.1 (2)	C22—C21—H21A	104.5
O2—C10—N2	124.6 (3)	C20—C21—H21B	104.5
O2—C10—C9	131.3 (3)	C22—C21—H21B	104.5
N2—C10—C9	104.0 (3)	H21A—C21—H21B	105.6
N1—C11—N3	122.3 (3)	C24—C23—N3	111.1 (3)
N1—C11—N2	113.7 (2)	C24—C23—H23A	109.4
N3—C11—N2	124.0 (3)	N3—C23—H23A	109.4
C13—C12—C17	120.0 (3)	C24—C23—H23B	109.4
C13—C12—N2	120.7 (3)	N3—C23—H23B	109.4
C17—C12—N2	119.2 (3)	H23A—C23—H23B	108.0
C12—C13—C14	119.4 (4)	C23—C24—C25	111.7 (3)
C12—C13—H13	120.3	C23—C24—H24A	109.3
C14—C13—H13	120.3	C25—C24—H24A	109.3
C15—C14—C13	119.7 (4)	C23—C24—H24B	109.3
C15—C14—H14	120.1	C25—C24—H24B	109.3
C13—C14—H14	120.1	H24A—C24—H24B	107.9
C14—C15—C16	120.1 (4)	C26—C25—C24	119.1 (3)
C14—C15—H15	120.0	C26—C25—H25A	107.5
C16—C15—H15	120.0	C24—C25—H25A	107.5
C15—C16—C17	121.0 (4)	C26—C25—H25B	107.5
C15—C16—H16	119.5	C24—C25—H25B	107.5
C17—C16—H16	119.5	H25A—C25—H25B	107.0
C16—C17—C12	119.7 (3)	C25—C26—C27	112.2 (4)
C16—C17—H17	120.1	C25—C26—H26A	109.2
C12—C17—H17	120.1	C27—C26—H26A	109.2
N3—C18'—C19'	107.7 (6)	C25—C26—H26B	109.2
N3—C18'—H18C	110.2	C27—C26—H26B	109.2
C19'—C18'—H18C	110.2	H26A—C26—H26B	107.9
N3—C18'—H18D	110.2	C26—C27—H27A	109.5
C19'—C18'—H18D	110.2	C26—C27—H27B	109.5
H18C—C18'—H18D	108.5	H27A—C27—H27B	109.5
C20'—C19'—C18'	119.3 (8)	C26—C27—H27C	109.5
C20'—C19'—H19C	107.5	H27A—C27—H27C	109.5
C18'—C19'—H19C	107.5	H27B—C27—H27C	109.5
C20'—C19'—H19D	107.5	C11—N1—C9	106.4 (2)
C18'—C19'—H19D	107.5	C10—N2—C11	106.7 (2)
H19C—C19'—H19D	107.0	C10—N2—C12	121.7 (2)
C21'—C20'—C19'	118.4 (8)	C11—N2—C12	131.5 (2)
C21'—C20'—H20C	107.7	C11—N3—C18	128.1 (4)
C19'—C20'—H20C	107.7	C11—N3—C18'	123.8 (3)
C21'—C20'—H20D	107.7	C18—N3—C18'	43.8 (3)
C19'—C20'—H20D	107.7	C11—N3—C23	115.7 (2)
H20C—C20'—H20D	107.1	C18—N3—C23	111.2 (3)
C20'—C21'—C22'	116.6 (9)	C18'—N3—C23	115.3 (3)
C20'—C21'—H21C	108.1	C2—O1—C1	118.0 (3)
C22'—C21'—H21C	108.1

O1—C2—C3—C5	−179.3 (3)	C24—C25—C26—C27	177.4 (4)
C4—C2—C3—C5	−0.9 (5)	N3—C11—N1—C9	−179.9 (3)
C3—C2—C4—C6	1.4 (5)	N2—C11—N1—C9	1.3 (3)
O1—C2—C4—C6	179.9 (3)	C8—C9—N1—C11	175.6 (3)
C2—C3—C5—C7	−0.1 (5)	C10—C9—N1—C11	−1.7 (3)
C2—C4—C6—C7	−0.9 (4)	O2—C10—N2—C11	−179.8 (3)
C4—C6—C7—C5	−0.1 (4)	C9—C10—N2—C11	−0.7 (3)
C4—C6—C7—C8	−177.8 (3)	O2—C10—N2—C12	−1.7 (5)
C3—C5—C7—C6	0.6 (4)	C9—C10—N2—C12	177.3 (3)
C3—C5—C7—C8	178.3 (3)	N1—C11—N2—C10	−0.3 (3)
C6—C7—C8—C9	−6.6 (5)	N3—C11—N2—C10	−179.1 (3)
C5—C7—C8—C9	175.8 (3)	N1—C11—N2—C12	−178.1 (3)
C7—C8—C9—N1	−2.8 (5)	N3—C11—N2—C12	3.1 (5)
C7—C8—C9—C10	174.1 (3)	C13—C12—N2—C10	−86.3 (4)
C8—C9—C10—O2	3.0 (5)	C17—C12—N2—C10	90.5 (4)
N1—C9—C10—O2	−179.5 (3)	C13—C12—N2—C11	91.3 (4)
C8—C9—C10—N2	−176.0 (2)	C17—C12—N2—C11	−92.0 (4)
N1—C9—C10—N2	1.5 (3)	N1—C11—N3—C18	−155.0 (4)
C17—C12—C13—C14	−0.2 (5)	N2—C11—N3—C18	23.7 (6)
N2—C12—C13—C14	176.5 (3)	N1—C11—N3—C18'	150.4 (4)
C12—C13—C14—C15	−0.3 (6)	N2—C11—N3—C18'	−30.9 (5)
C13—C14—C15—C16	1.9 (7)	N1—C11—N3—C23	−2.8 (4)
C14—C15—C16—C17	−3.1 (7)	N2—C11—N3—C23	175.9 (3)
C15—C16—C17—C12	2.5 (6)	C19—C18—N3—C11	−125.9 (6)
C13—C12—C17—C16	−0.9 (5)	C19—C18—N3—C18'	−24.2 (6)
N2—C12—C17—C16	−177.6 (3)	C19—C18—N3—C23	80.8 (7)
N3—C18'—C19'—C20'	165.8 (7)	C19'—C18'—N3—C11	119.8 (6)
C18'—C19'—C20'—C21'	74.3 (14)	C19'—C18'—N3—C18	7.8 (6)
C19'—C20'—C21'—C22'	158.6 (11)	C19'—C18'—N3—C23	−87.0 (6)
N3—C18—C19—C20	162.9 (15)	C24—C23—N3—C11	81.5 (3)
C18—C19—C20—C21	7 (4)	C24—C23—N3—C18	−121.7 (4)
C19—C20—C21—C22	−171.2 (18)	C24—C23—N3—C18'	−73.9 (4)
N3—C23—C24—C25	176.7 (3)	C3—C2—O1—C1	−1.5 (5)
C23—C24—C25—C26	65.0 (5)	C4—C2—O1—C1	180.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···N1	0.93	2.39	3.037 (4)	127

Experimental details

Crystal data
Chemical formula	C₂₇H₃₅N₃O₂
M_r	433.58
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	9.4091 (8), 11.4405 (9), 11.9354 (10)
α, β, γ (°)	90.080 (2), 94.746 (2), 102.044 (2)
V (Å³)	1251.96 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10980, 4871, 1734
R_int	0.085
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.183, 0.82
No. of reflections	4871
No. of parameters	339
No. of restraints	83
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.16

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXTL.