Methyl 3-[(1H-benzimidazol-1-yl)meth-yl]-1-methyl-4-(4-methyl-phen-yl)-2'-oxopyrrolidine-2-spiro-3'-1-benzimidazole-3-carboxyl-ate.

In the title compound, C(29)H(28)N(4)O(3), the pyrrolidine ring adopts a twist conformation whereas the oxindole and benzimidazole residues are approximately planar with maximum deviations of 0.159 (1) and 0.011 (1) Å, respectively. The oxindole residue is almost perpendicular to the benzimidazole residue, making a dihedral angle of 89.2 (1)°. The methyl-substituted benzene ring is oriented at angles of 47.7 (1) and 71.0 (1)°, respectively, with respect to the oxindole and benzimidazole residues. An intra-molecular C-H⋯O hydrogen bond is observed. In the crystal, mol-ecules associate via N-H⋯N hydrogen bonds, forming R(2) (2)(9) dimers.

Related literature

For general background to pyrrolidine derivatives, see: Obniska et al. (2010 ▶); Morais et al. (2009 ▶); Bello et al. (2010 ▶); Moreno-Clavijo et al. (2009 ▶); Cheng et al. (2008 ▶). For related structures, see: Aravindan et al. (2004 ▶); Selvanayagam et al. (2005 ▶); Seshadri et al. (2003 ▶). For ring-puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C29H28N4O3

M = 480.55

Triclinic,

a = 9.7605 (5) Å

b = 11.2823 (6) Å

c = 12.2333 (7) Å

α = 79.960 (1)°

β = 69.539 (1)°

γ = 85.358 (1)°

V = 1242.53 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 292 K

0.26 × 0.24 × 0.22 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

14287 measured reflections

5705 independent reflections

5041 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.131

S = 1.04

5705 reflections

328 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810035312/bt5341sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035312/bt5341Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C29H28N4O3	Z = 2
Mr = 480.55	F(000) = 508
Triclinic, P1	Dx = 1.284 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7605 (5) Å	Cell parameters from 8628 reflections
b = 11.2823 (6) Å	θ = 2.0–27.4°
c = 12.2333 (7) Å	µ = 0.09 mm−1
α = 79.960 (1)°	T = 292 K
β = 69.539 (1)°	Block, colourless
γ = 85.358 (1)°	0.26 × 0.24 × 0.22 mm
V = 1242.53 (12) Å3

Bruker SMART APEX CCD area-detector diffractometer	5041 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.017
graphite	θmax = 28.0°, θmin = 1.8°
ω scans	h = −12→12
14287 measured reflections	k = −14→14
5705 independent reflections	l = −15→16

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0777P)2 + 0.1893P] where P = (Fo2 + 2Fc2)/3
5705 reflections	(Δ/σ)max < 0.001
328 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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. 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
O1	−0.02562 (10)	0.75938 (10)	0.40536 (9)	0.0564 (2)
O2	0.45463 (10)	0.62452 (9)	0.06224 (9)	0.0556 (2)
O3	0.30370 (10)	0.55640 (7)	0.24567 (8)	0.0475 (2)
N1	0.19339 (11)	0.93029 (8)	0.24498 (9)	0.0415 (2)
N2	0.16540 (13)	0.69375 (10)	0.47180 (9)	0.0498 (3)
H2	0.1161	0.6547	0.5395	0.060*
N3	0.05799 (10)	0.60212 (9)	0.17842 (8)	0.0392 (2)
N4	−0.04307 (15)	0.42908 (11)	0.28856 (10)	0.0592 (3)
C1	0.30089 (16)	0.97153 (11)	0.12846 (10)	0.0467 (3)
H1A	0.3882	0.9989	0.1363	0.056*
H1B	0.2603	1.0371	0.0857	0.056*
C2	0.33690 (12)	0.86094 (10)	0.06345 (9)	0.0371 (2)
H2A	0.4416	0.8431	0.0465	0.045*
C3	0.25260 (11)	0.75294 (9)	0.15982 (9)	0.0337 (2)
C4	0.23182 (12)	0.80336 (10)	0.27776 (9)	0.0363 (2)
C5	0.18078 (18)	1.00891 (12)	0.33182 (12)	0.0546 (3)
H5A	0.2735	1.0115	0.3421	0.082*
H5B	0.1087	0.9780	0.4059	0.082*
H5C	0.1518	1.0886	0.3043	0.082*
C6	0.36486 (13)	0.77598 (10)	0.31879 (10)	0.0383 (2)
C7	0.51257 (14)	0.80220 (12)	0.26535 (11)	0.0468 (3)
H7	0.5466	0.8478	0.1905	0.056*
C8	0.60970 (16)	0.75910 (14)	0.32568 (14)	0.0560 (3)
H8	0.7085	0.7767	0.2906	0.067*
C9	0.55981 (18)	0.69048 (15)	0.43698 (14)	0.0625 (4)
H9	0.6259	0.6620	0.4753	0.075*
C10	0.41285 (18)	0.66350 (14)	0.49225 (13)	0.0592 (4)
H10	0.3794	0.6173	0.5669	0.071*
C11	0.31760 (14)	0.70791 (11)	0.43221 (10)	0.0438 (3)
C12	0.10539 (13)	0.74875 (11)	0.39100 (10)	0.0427 (3)
C13	0.35074 (12)	0.63904 (10)	0.14798 (10)	0.0380 (2)
C14	0.3828 (2)	0.44195 (14)	0.24091 (17)	0.0713 (5)
H14A	0.3969	0.4160	0.1670	0.107*
H14B	0.3277	0.3831	0.3046	0.107*
H14C	0.4762	0.4509	0.2480	0.107*
C15	0.10345 (12)	0.72765 (10)	0.14655 (10)	0.0384 (2)
H15A	0.0272	0.7758	0.1952	0.046*
H15B	0.1105	0.7551	0.0651	0.046*
C16	−0.02908 (15)	0.54492 (13)	0.28527 (11)	0.0517 (3)
H16	−0.0745	0.5843	0.3499	0.062*
C17	0.04075 (15)	0.40654 (11)	0.17515 (12)	0.0481 (3)
C18	0.06481 (18)	0.29959 (12)	0.12571 (15)	0.0613 (4)
H18	0.0230	0.2278	0.1704	0.074*
C19	0.15226 (18)	0.30483 (13)	0.00910 (16)	0.0616 (4)
H19	0.1696	0.2351	−0.0251	0.074*
C20	0.21573 (15)	0.41222 (14)	−0.05946 (14)	0.0554 (3)
H20	0.2742	0.4120	−0.1379	0.066*
C21	0.19363 (13)	0.51890 (12)	−0.01339 (11)	0.0461 (3)
H21	0.2356	0.5903	−0.0590	0.055*
C22	0.10513 (12)	0.51376 (10)	0.10505 (10)	0.0390 (2)
C23	0.31253 (12)	0.88215 (10)	−0.05502 (9)	0.0361 (2)
C24	0.41258 (14)	0.83543 (11)	−0.15145 (11)	0.0440 (3)
H24	0.4914	0.7881	−0.1418	0.053*
C25	0.39601 (17)	0.85871 (13)	−0.26221 (11)	0.0536 (3)
H25	0.4643	0.8269	−0.3252	0.064*
C26	0.27911 (17)	0.92865 (12)	−0.27996 (11)	0.0505 (3)
C27	0.17746 (15)	0.97312 (11)	−0.18349 (11)	0.0475 (3)
H27	0.0969	1.0180	−0.1927	0.057*
C28	0.19461 (13)	0.95146 (11)	−0.07328 (10)	0.0428 (3)
H28	0.1263	0.9837	−0.0106	0.051*
C29	0.2617 (3)	0.95730 (18)	−0.40035 (15)	0.0789 (5)
H29A	0.3561	0.9562	−0.4609	0.118*
H29B	0.2167	1.0357	−0.4086	0.118*
H29C	0.2013	0.8982	−0.4077	0.118*

	U11	U22	U33	U12	U13	U23
O1	0.0441 (5)	0.0703 (6)	0.0480 (5)	−0.0038 (4)	−0.0057 (4)	−0.0113 (4)
O2	0.0484 (5)	0.0570 (5)	0.0528 (5)	0.0094 (4)	−0.0084 (4)	−0.0094 (4)
O3	0.0602 (5)	0.0349 (4)	0.0466 (5)	0.0031 (4)	−0.0212 (4)	0.0000 (3)
N1	0.0536 (6)	0.0351 (5)	0.0368 (5)	0.0028 (4)	−0.0177 (4)	−0.0051 (4)
N2	0.0576 (6)	0.0524 (6)	0.0318 (5)	−0.0095 (5)	−0.0096 (4)	0.0048 (4)
N3	0.0406 (5)	0.0383 (5)	0.0365 (5)	−0.0090 (4)	−0.0115 (4)	0.0004 (4)
N4	0.0737 (8)	0.0534 (6)	0.0456 (6)	−0.0246 (6)	−0.0172 (6)	0.0090 (5)
C1	0.0694 (8)	0.0361 (6)	0.0368 (6)	−0.0109 (5)	−0.0216 (5)	0.0000 (5)
C2	0.0427 (5)	0.0368 (5)	0.0314 (5)	−0.0079 (4)	−0.0135 (4)	0.0008 (4)
C3	0.0368 (5)	0.0332 (5)	0.0298 (5)	−0.0030 (4)	−0.0112 (4)	−0.0009 (4)
C4	0.0406 (5)	0.0359 (5)	0.0307 (5)	−0.0023 (4)	−0.0114 (4)	−0.0018 (4)
C5	0.0766 (9)	0.0460 (7)	0.0448 (7)	0.0063 (6)	−0.0237 (6)	−0.0134 (5)
C6	0.0470 (6)	0.0363 (5)	0.0331 (5)	−0.0020 (4)	−0.0163 (4)	−0.0036 (4)
C7	0.0483 (6)	0.0503 (7)	0.0425 (6)	−0.0057 (5)	−0.0179 (5)	−0.0016 (5)
C8	0.0509 (7)	0.0625 (8)	0.0613 (8)	0.0006 (6)	−0.0275 (6)	−0.0106 (7)
C9	0.0697 (9)	0.0665 (9)	0.0634 (9)	0.0109 (7)	−0.0415 (8)	−0.0080 (7)
C10	0.0788 (10)	0.0575 (8)	0.0446 (7)	0.0028 (7)	−0.0319 (7)	0.0039 (6)
C11	0.0566 (7)	0.0398 (6)	0.0351 (6)	−0.0025 (5)	−0.0175 (5)	−0.0017 (4)
C12	0.0463 (6)	0.0436 (6)	0.0343 (5)	−0.0047 (5)	−0.0075 (5)	−0.0070 (4)
C13	0.0406 (5)	0.0375 (5)	0.0389 (5)	−0.0009 (4)	−0.0177 (4)	−0.0046 (4)
C14	0.0865 (11)	0.0433 (7)	0.0834 (11)	0.0160 (7)	−0.0373 (9)	0.0012 (7)
C15	0.0398 (5)	0.0351 (5)	0.0400 (6)	−0.0048 (4)	−0.0158 (4)	0.0010 (4)
C16	0.0561 (7)	0.0544 (7)	0.0385 (6)	−0.0177 (6)	−0.0094 (5)	0.0022 (5)
C17	0.0555 (7)	0.0417 (6)	0.0492 (7)	−0.0115 (5)	−0.0243 (6)	0.0056 (5)
C18	0.0771 (10)	0.0371 (6)	0.0793 (10)	−0.0093 (6)	−0.0426 (8)	0.0029 (6)
C19	0.0688 (9)	0.0489 (7)	0.0816 (11)	0.0077 (6)	−0.0408 (8)	−0.0205 (7)
C20	0.0486 (7)	0.0646 (8)	0.0584 (8)	0.0025 (6)	−0.0205 (6)	−0.0209 (7)
C21	0.0416 (6)	0.0511 (7)	0.0463 (6)	−0.0083 (5)	−0.0150 (5)	−0.0063 (5)
C22	0.0391 (5)	0.0378 (5)	0.0428 (6)	−0.0057 (4)	−0.0184 (5)	−0.0020 (4)
C23	0.0426 (5)	0.0341 (5)	0.0305 (5)	−0.0078 (4)	−0.0121 (4)	0.0003 (4)
C24	0.0506 (6)	0.0419 (6)	0.0395 (6)	0.0020 (5)	−0.0155 (5)	−0.0075 (5)
C25	0.0706 (9)	0.0530 (7)	0.0369 (6)	0.0040 (6)	−0.0159 (6)	−0.0139 (5)
C26	0.0725 (8)	0.0458 (6)	0.0394 (6)	−0.0056 (6)	−0.0270 (6)	−0.0042 (5)
C27	0.0556 (7)	0.0434 (6)	0.0462 (6)	−0.0016 (5)	−0.0243 (6)	0.0003 (5)
C28	0.0449 (6)	0.0432 (6)	0.0368 (6)	−0.0017 (5)	−0.0115 (5)	−0.0019 (5)
C29	0.1203 (16)	0.0809 (11)	0.0495 (8)	0.0099 (11)	−0.0479 (10)	−0.0122 (8)

O1—C12	1.2271 (16)	C9—C10	1.389 (2)
O2—C13	1.2019 (14)	C9—H9	0.9300
O3—C13	1.3437 (14)	C10—C11	1.3888 (18)
O3—C14	1.4492 (16)	C10—H10	0.9300
N1—C5	1.4662 (16)	C14—H14A	0.9600
N1—C1	1.4668 (16)	C14—H14B	0.9600
N1—C4	1.4732 (14)	C14—H14C	0.9600
N2—C12	1.3555 (16)	C15—H15A	0.9700
N2—C11	1.4055 (17)	C15—H15B	0.9700
N2—H2	0.8600	C16—H16	0.9300
N3—C16	1.3657 (15)	C17—C22	1.4065 (16)
N3—C22	1.4000 (16)	C17—C18	1.409 (2)
N3—C15	1.4639 (14)	C18—C19	1.376 (2)
N4—C16	1.3172 (19)	C18—H18	0.9300
N4—C17	1.3981 (19)	C19—C20	1.400 (2)
C1—C2	1.5467 (16)	C19—H19	0.9300
C1—H1A	0.9700	C20—C21	1.3866 (19)
C1—H1B	0.9700	C20—H20	0.9300
C2—C23	1.5247 (14)	C21—C22	1.3973 (17)
C2—C3	1.5921 (14)	C21—H21	0.9300
C2—H2A	0.9800	C23—C24	1.3968 (16)
C3—C13	1.5357 (15)	C23—C28	1.3998 (16)
C3—C15	1.5735 (15)	C24—C25	1.3976 (18)
C3—C4	1.5840 (15)	C24—H24	0.9300
C4—C6	1.5396 (16)	C25—C26	1.393 (2)
C4—C12	1.5658 (15)	C25—H25	0.9300
C5—H5A	0.9600	C26—C27	1.391 (2)
C5—H5B	0.9600	C26—C29	1.5173 (18)
C5—H5C	0.9600	C27—C28	1.3934 (17)
C6—C7	1.3915 (17)	C27—H27	0.9300
C6—C11	1.4021 (16)	C28—H28	0.9300
C7—C8	1.4033 (18)	C29—H29A	0.9600
C7—H7	0.9300	C29—H29B	0.9600
C8—C9	1.386 (2)	C29—H29C	0.9600
C8—H8	0.9300
C13—O3—C14	115.61 (11)	N2—C12—C4	108.20 (10)
C5—N1—C1	113.09 (10)	O2—C13—O3	124.23 (10)
C5—N1—C4	115.51 (9)	O2—C13—C3	124.75 (10)
C1—N1—C4	106.21 (9)	O3—C13—C3	111.01 (9)
C12—N2—C11	112.18 (10)	O3—C14—H14A	109.5
C12—N2—H2	123.9	O3—C14—H14B	109.5
C11—N2—H2	123.9	H14A—C14—H14B	109.5
C16—N3—C22	105.96 (10)	O3—C14—H14C	109.5
C16—N3—C15	128.19 (11)	H14A—C14—H14C	109.5
C22—N3—C15	125.72 (9)	H14B—C14—H14C	109.5
C16—N4—C17	104.88 (11)	N3—C15—C3	116.04 (9)
N1—C1—C2	105.55 (9)	N3—C15—H15A	108.3
N1—C1—H1A	110.6	C3—C15—H15A	108.3
C2—C1—H1A	110.6	N3—C15—H15B	108.3
N1—C1—H1B	110.6	C3—C15—H15B	108.3
C2—C1—H1B	110.6	H15A—C15—H15B	107.4
H1A—C1—H1B	108.8	N4—C16—N3	114.03 (12)
C23—C2—C1	114.32 (9)	N4—C16—H16	123.0
C23—C2—C3	117.51 (9)	N3—C16—H16	123.0
C1—C2—C3	104.77 (8)	N4—C17—C22	109.58 (11)
C23—C2—H2A	106.5	N4—C17—C18	130.71 (12)
C1—C2—H2A	106.5	C22—C17—C18	119.71 (13)
C3—C2—H2A	106.5	C19—C18—C17	117.84 (13)
C13—C3—C15	109.64 (9)	C19—C18—H18	121.1
C13—C3—C4	112.06 (8)	C17—C18—H18	121.1
C15—C3—C4	113.01 (9)	C18—C19—C20	121.77 (14)
C13—C3—C2	109.12 (9)	C18—C19—H19	119.1
C15—C3—C2	112.02 (8)	C20—C19—H19	119.1
C4—C3—C2	100.71 (8)	C21—C20—C19	121.69 (14)
N1—C4—C6	118.20 (9)	C21—C20—H20	119.2
N1—C4—C12	108.16 (9)	C19—C20—H20	119.2
C6—C4—C12	101.17 (9)	C20—C21—C22	116.65 (12)
N1—C4—C3	100.65 (8)	C20—C21—H21	121.7
C6—C4—C3	112.70 (9)	C22—C21—H21	121.7
C12—C4—C3	116.68 (9)	C21—C22—N3	132.09 (11)
N1—C5—H5A	109.5	C21—C22—C17	122.34 (12)
N1—C5—H5B	109.5	N3—C22—C17	105.55 (10)
H5A—C5—H5B	109.5	C24—C23—C28	117.53 (10)
N1—C5—H5C	109.5	C24—C23—C2	120.08 (10)
H5A—C5—H5C	109.5	C28—C23—C2	122.35 (10)
H5B—C5—H5C	109.5	C23—C24—C25	120.96 (12)
C7—C6—C11	118.67 (11)	C23—C24—H24	119.5
C7—C6—C4	133.14 (10)	C25—C24—H24	119.5
C11—C6—C4	108.15 (10)	C26—C25—C24	121.19 (12)
C6—C7—C8	119.29 (12)	C26—C25—H25	119.4
C6—C7—H7	120.4	C24—C25—H25	119.4
C8—C7—H7	120.4	C27—C26—C25	118.01 (11)
C9—C8—C7	120.61 (13)	C27—C26—C29	120.20 (14)
C9—C8—H8	119.7	C25—C26—C29	121.79 (14)
C7—C8—H8	119.7	C26—C27—C28	120.98 (12)
C8—C9—C10	121.15 (13)	C26—C27—H27	119.5
C8—C9—H9	119.4	C28—C27—H27	119.5
C10—C9—H9	119.4	C27—C28—C23	121.32 (11)
C9—C10—C11	117.67 (13)	C27—C28—H28	119.3
C9—C10—H10	121.2	C23—C28—H28	119.3
C11—C10—H10	121.2	C26—C29—H29A	109.5
C10—C11—C6	122.60 (13)	C26—C29—H29B	109.5
C10—C11—N2	127.34 (12)	H29A—C29—H29B	109.5
C6—C11—N2	110.06 (10)	C26—C29—H29C	109.5
O1—C12—N2	126.27 (11)	H29A—C29—H29C	109.5
O1—C12—C4	125.45 (11)	H29B—C29—H29C	109.5
C5—N1—C1—C2	161.69 (10)	C6—C4—C12—N2	−4.58 (12)
C4—N1—C1—C2	33.99 (12)	C3—C4—C12—N2	118.07 (11)
N1—C1—C2—C23	124.14 (10)	C14—O3—C13—O2	−2.91 (18)
N1—C1—C2—C3	−5.90 (12)	C14—O3—C13—C3	176.04 (12)
C23—C2—C3—C13	92.40 (11)	C15—C3—C13—O2	104.57 (13)
C1—C2—C3—C13	−139.46 (9)	C4—C3—C13—O2	−129.11 (12)
C23—C2—C3—C15	−29.19 (13)	C2—C3—C13—O2	−18.46 (15)
C1—C2—C3—C15	98.95 (10)	C15—C3—C13—O3	−74.38 (11)
C23—C2—C3—C4	−149.56 (10)	C4—C3—C13—O3	51.94 (12)
C1—C2—C3—C4	−21.42 (11)	C2—C3—C13—O3	162.60 (9)
C5—N1—C4—C6	−50.74 (14)	C16—N3—C15—C3	92.19 (15)
C1—N1—C4—C6	75.51 (12)	C22—N3—C15—C3	−83.07 (13)
C5—N1—C4—C12	63.29 (13)	C13—C3—C15—N3	26.13 (13)
C1—N1—C4—C12	−170.47 (9)	C4—C3—C15—N3	−99.65 (11)
C5—N1—C4—C3	−173.86 (10)	C2—C3—C15—N3	147.43 (9)
C1—N1—C4—C3	−47.62 (11)	C17—N4—C16—N3	−0.14 (17)
C13—C3—C4—N1	156.94 (9)	C22—N3—C16—N4	0.01 (16)
C15—C3—C4—N1	−78.59 (10)	C15—N3—C16—N4	−175.99 (12)
C2—C3—C4—N1	41.06 (10)	C16—N4—C17—C22	0.22 (15)
C13—C3—C4—C6	30.07 (12)	C16—N4—C17—C18	−178.59 (15)
C15—C3—C4—C6	154.54 (9)	N4—C17—C18—C19	178.97 (14)
C2—C3—C4—C6	−85.80 (10)	C22—C17—C18—C19	0.3 (2)
C13—C3—C4—C12	−86.36 (12)	C17—C18—C19—C20	−0.2 (2)
C15—C3—C4—C12	38.11 (13)	C18—C19—C20—C21	0.0 (2)
C2—C3—C4—C12	157.77 (9)	C19—C20—C21—C22	0.17 (19)
N1—C4—C6—C7	−59.69 (17)	C20—C21—C22—N3	−178.63 (12)
C12—C4—C6—C7	−177.48 (13)	C20—C21—C22—C17	−0.07 (18)
C3—C4—C6—C7	57.16 (16)	C16—N3—C22—C21	178.86 (13)
N1—C4—C6—C11	122.37 (11)	C15—N3—C22—C21	−5.02 (19)
C12—C4—C6—C11	4.58 (11)	C16—N3—C22—C17	0.13 (13)
C3—C4—C6—C11	−120.78 (10)	C15—N3—C22—C17	176.25 (10)
C11—C6—C7—C8	0.58 (18)	N4—C17—C22—C21	−179.10 (11)
C4—C6—C7—C8	−177.19 (12)	C18—C17—C22—C21	−0.14 (19)
C6—C7—C8—C9	0.4 (2)	N4—C17—C22—N3	−0.21 (14)
C7—C8—C9—C10	−0.6 (2)	C18—C17—C22—N3	178.75 (11)
C8—C9—C10—C11	−0.1 (2)	C1—C2—C23—C24	139.36 (11)
C9—C10—C11—C6	1.2 (2)	C3—C2—C23—C24	−97.22 (12)
C9—C10—C11—N2	−178.74 (13)	C1—C2—C23—C28	−38.27 (14)
C7—C6—C11—C10	−1.40 (19)	C3—C2—C23—C28	85.16 (13)
C4—C6—C11—C10	176.88 (12)	C28—C23—C24—C25	0.84 (18)
C7—C6—C11—N2	178.53 (11)	C2—C23—C24—C25	−176.90 (11)
C4—C6—C11—N2	−3.18 (13)	C23—C24—C25—C26	−0.3 (2)
C12—N2—C11—C10	179.99 (13)	C24—C25—C26—C27	−1.1 (2)
C12—N2—C11—C6	0.05 (15)	C24—C25—C26—C29	178.44 (15)
C11—N2—C12—O1	−173.75 (12)	C25—C26—C27—C28	2.0 (2)
C11—N2—C12—C4	3.05 (14)	C29—C26—C27—C28	−177.59 (14)
N1—C4—C12—O1	47.38 (15)	C26—C27—C28—C23	−1.45 (19)
C6—C4—C12—O1	172.25 (12)	C24—C23—C28—C27	0.02 (17)
C3—C4—C12—O1	−65.10 (16)	C2—C23—C28—C27	177.70 (10)
N1—C4—C12—N2	−129.44 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N4i	0.86	2.05	2.888 (2)	165
C16—H16···O1	0.93	2.33	3.050 (2)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N4i	0.86	2.05	2.888 (2)	165
C16—H16⋯O1	0.93	2.33	3.050 (2)	134

Symmetry code: (i) .