Methyl 3-(2-chlorophenyl)-2-(1H-indol-3-ylmethyl)-5-[1-(4-methoxyphenyl)-4-oxo-3-phenylazetidin-2-yl]-4-nitropyr-rolidine-2-carboxylate.

In the mol-ecule of the title compound, C(37)H(33)ClN(4)O(6), the four-membered β-lactam ring is essentially planar and is oriented at dihedral angles of 30.0 (1), 76.3 (1) and 30.9 (1)° with respect to the methoxy-phenyl ring, the phenyl ring and the indole unit, respectively. The pyrrolidine ring adopts a twist conformation. Intra-molecular C-H⋯Cl and C-H⋯O hydrogen bonds result in the formation of two five- and one six-membered rings. In the crystal structure, inter-molecular C-H⋯O and N-H⋯O hydrogen bonds link the mol-ecules. A weak π⋯π inter-action between the pyrrole rings further stabilizes the structure, with a centroid-centroid distance of 3.806 (2) Å.

Related literature

For general background, see: Bruggink (2001 ▶); Morin & Gorman (1982 ▶); Katritzky et al. (1996 ▶); Georg (1993 ▶); Coyne et al. (2007 ▶); Dobrowolski et al. (2004 ▶); Cha et al. (2006 ▶). For related literature, see: Bhaskaran et al. (2006 ▶); Kamala et al. (2008 ▶); Ülkü et al. (1997 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Nardelli (1995 ▶).

Experimental

Crystal data

C37H33ClN4O6

M = 665.12

Triclinic,

a = 10.399 (3) Å

b = 12.500 (3) Å

c = 14.211 (3) Å

α = 93.766 (6)°

β = 99.962 (6)°

γ = 114.066 (5)°

V = 1642.1 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.17 mm−1

T = 293 (2) K

0.30 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEX2 CCD diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.951, T max = 0.973

25481 measured reflections

5563 independent reflections

3770 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.317

S = 1.10

5563 reflections

433 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.64 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808013585/hk2460sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013585/hk2460Isup2.hkl

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

C37H33ClN4O6	Z = 2
Mr = 665.12	F000 = 696
Triclinic, P1	Dx = 1.345 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 10.399 (3) Å	Cell parameters from 8315 reflections
b = 12.500 (3) Å	θ = 2.5–31.6º
c = 14.211 (3) Å	µ = 0.17 mm−1
α = 93.766 (6)º	T = 293 (2) K
β = 99.962 (6)º	Prism, colourless
γ = 114.066 (5)º	0.30 × 0.20 × 0.16 mm
V = 1642.1 (7) Å3

Bruker KAPPA APEX2 CCD diffractometer	5563 independent reflections
Radiation source: fine-focus sealed tube	3770 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.057
T = 294(2) K	θmax = 25.0º
ω and φ scans	θmin = 1.5º
Absorption correction: multi-scan(Blessing, 1995)	h = −12→12
Tmin = 0.951, Tmax = 0.973	k = −14→14
25481 measured reflections	l = −16→16

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)] = 0.067	H-atom parameters constrained
wR(F2) = 0.317	w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
5563 reflections	Δρmax = 0.51 e Å−3
433 parameters	Δρmin = −0.64 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 > 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
Cl1	0.27147 (16)	0.62053 (13)	0.03791 (11)	0.0912 (5)
O1	0.4619 (3)	0.3522 (3)	0.1048 (2)	0.0620 (8)
O2	0.4973 (3)	0.5325 (3)	0.16978 (19)	0.0549 (7)
O3	0.1219 (3)	0.2147 (3)	−0.0280 (2)	0.0690 (9)
O4	−0.0986 (3)	0.1137 (3)	−0.02304 (19)	0.0646 (8)
O5	−0.1691 (3)	−0.1217 (3)	0.3043 (3)	0.0861 (12)
O6	0.4562 (3)	−0.1339 (3)	0.4179 (2)	0.0647 (9)
N1	0.5503 (4)	0.3211 (3)	0.4608 (2)	0.0500 (8)
H1A	0.5602	0.2674	0.4921	0.060*
N2	0.2433 (3)	0.2437 (2)	0.19400 (18)	0.0340 (6)
H2	0.2943	0.2039	0.1976	0.041*
N3	0.0198 (3)	0.1926 (3)	0.0102 (2)	0.0441 (8)
N4	0.0375 (3)	0.0089 (2)	0.2561 (2)	0.0406 (7)
C1	0.4247 (4)	0.3105 (3)	0.4029 (2)	0.0452 (9)
H1	0.3372	0.2435	0.3914	0.054*
C2	0.4455 (3)	0.4115 (3)	0.3646 (2)	0.0344 (7)
C3	0.5947 (3)	0.4900 (3)	0.4004 (2)	0.0355 (8)
C4	0.6834 (4)	0.6067 (3)	0.3897 (2)	0.0464 (9)
H4	0.6465	0.6488	0.3504	0.056*
C5	0.8251 (4)	0.6574 (4)	0.4383 (3)	0.0614 (11)
H5	0.8838	0.7347	0.4320	0.074*
C6	0.8836 (4)	0.5963 (5)	0.4969 (3)	0.0669 (13)
H6	0.9802	0.6335	0.5289	0.080*
C7	0.8008 (4)	0.4815 (5)	0.5083 (3)	0.0592 (12)
H7	0.8402	0.4400	0.5465	0.071*
C8	0.6570 (4)	0.4301 (3)	0.4609 (2)	0.0411 (8)
C9	0.3323 (3)	0.4348 (3)	0.3002 (2)	0.0340 (7)
H9A	0.3665	0.5194	0.2999	0.041*
H9B	0.2457	0.4079	0.3260	0.041*
C10	0.2943 (3)	0.3712 (3)	0.1948 (2)	0.0310 (7)
C11	0.1669 (3)	0.3868 (3)	0.1245 (2)	0.0335 (7)
H11	0.1957	0.4033	0.0630	0.040*
C12	0.0405 (3)	0.2628 (3)	0.1066 (2)	0.0331 (7)
H12	−0.0490	0.2678	0.1139	0.040*
C13	0.0886 (3)	0.1980 (3)	0.1857 (2)	0.0315 (7)
H13	0.0732	0.2268	0.2468	0.038*
C14	0.0125 (3)	0.0649 (3)	0.1707 (2)	0.0357 (7)
H14	0.0309	0.0299	0.1137	0.043*
C15	−0.1531 (3)	0.0061 (3)	0.1733 (3)	0.0458 (9)
H15	−0.2101	−0.0532	0.1159	0.055*
C16	−0.1057 (4)	−0.0505 (3)	0.2560 (3)	0.0519 (10)
C17	0.1534 (3)	−0.0169 (3)	0.2985 (2)	0.0378 (8)
C18	0.2642 (3)	−0.0060 (3)	0.2526 (2)	0.0393 (8)
H18	0.2685	0.0256	0.1952	0.047*
C19	0.3685 (3)	−0.0420 (3)	0.2917 (3)	0.0430 (8)
H19	0.4434	−0.0337	0.2610	0.052*
C20	0.3619 (4)	−0.0899 (3)	0.3756 (3)	0.0460 (9)
C21	0.2550 (4)	−0.0962 (4)	0.4239 (3)	0.0544 (10)
H21	0.2533	−0.1250	0.4826	0.065*
C22	0.1513 (4)	−0.0600 (4)	0.3857 (3)	0.0509 (10)
H22	0.0796	−0.0645	0.4185	0.061*
C23	0.5611 (5)	−0.1357 (5)	0.3669 (4)	0.0807 (16)
H23A	0.6198	−0.1683	0.4029	0.121*
H23B	0.6208	−0.0564	0.3585	0.121*
H23C	0.5137	−0.1838	0.3048	0.121*
C24	−0.2264 (3)	0.0835 (3)	0.1965 (3)	0.0418 (9)
C25	−0.1948 (4)	0.1455 (3)	0.2876 (3)	0.0461 (9)
H25	−0.1276	0.1389	0.3365	0.055*
C26	−0.2613 (4)	0.2174 (4)	0.3075 (3)	0.0555 (10)
H26	−0.2388	0.2582	0.3696	0.067*
C27	−0.3605 (4)	0.2289 (4)	0.2362 (3)	0.0605 (11)
H27	−0.4052	0.2774	0.2495	0.073*
C28	−0.3929 (4)	0.1674 (4)	0.1442 (3)	0.0618 (12)
H28	−0.4591	0.1752	0.0953	0.074*
C29	−0.3278 (4)	0.0951 (4)	0.1250 (3)	0.0537 (10)
H29	−0.3517	0.0531	0.0632	0.064*
C30	0.1230 (3)	0.4815 (3)	0.1585 (2)	0.0386 (8)
C31	0.0321 (4)	0.4623 (4)	0.2234 (3)	0.0473 (9)
H31	0.0003	0.3906	0.2472	0.057*
C32	−0.0116 (5)	0.5464 (4)	0.2530 (3)	0.0664 (13)
H32	−0.0731	0.5307	0.2957	0.080*
C33	0.0349 (7)	0.6529 (5)	0.2198 (4)	0.0842 (18)
H33	0.0062	0.7101	0.2406	0.101*
C34	0.1243 (6)	0.6751 (4)	0.1557 (4)	0.0775 (16)
H34	0.1564	0.7477	0.1333	0.093*
C35	0.1674 (4)	0.5889 (3)	0.1239 (3)	0.0537 (10)
C36	0.4283 (3)	0.4159 (3)	0.1513 (2)	0.0384 (8)
C37	0.6263 (4)	0.5862 (5)	0.1315 (3)	0.0768 (15)
H37A	0.6678	0.6708	0.1491	0.115*
H37B	0.6014	0.5664	0.0623	0.115*
H37C	0.6950	0.5570	0.1577	0.115*

	U11	U22	U33	U12	U13	U23
Cl1	0.1027 (10)	0.0749 (10)	0.1001 (11)	0.0317 (8)	0.0319 (8)	0.0577 (8)
O1	0.0716 (17)	0.076 (2)	0.0706 (19)	0.0510 (17)	0.0408 (14)	0.0291 (16)
O2	0.0497 (14)	0.0547 (19)	0.0521 (16)	0.0091 (13)	0.0214 (11)	0.0149 (13)
O3	0.081 (2)	0.083 (2)	0.0504 (17)	0.0411 (18)	0.0232 (15)	−0.0032 (16)
O4	0.0702 (18)	0.060 (2)	0.0491 (16)	0.0255 (16)	−0.0112 (13)	−0.0109 (14)
O5	0.0532 (16)	0.084 (2)	0.149 (3)	0.0374 (16)	0.0485 (19)	0.078 (2)
O6	0.0597 (15)	0.083 (2)	0.079 (2)	0.0484 (16)	0.0245 (14)	0.0487 (17)
N1	0.0702 (19)	0.057 (2)	0.0369 (16)	0.0401 (18)	0.0100 (14)	0.0201 (15)
N2	0.0349 (12)	0.0346 (16)	0.0398 (15)	0.0216 (12)	0.0076 (10)	0.0116 (12)
N3	0.0589 (18)	0.0459 (19)	0.0339 (16)	0.0323 (16)	0.0013 (13)	0.0045 (14)
N4	0.0355 (13)	0.0350 (17)	0.0586 (18)	0.0193 (12)	0.0137 (12)	0.0177 (14)
C1	0.0529 (18)	0.047 (2)	0.0362 (18)	0.0206 (17)	0.0092 (14)	0.0129 (17)
C2	0.0423 (16)	0.040 (2)	0.0277 (16)	0.0230 (15)	0.0104 (12)	0.0111 (14)
C3	0.0443 (16)	0.044 (2)	0.0240 (15)	0.0256 (15)	0.0068 (12)	0.0030 (14)
C4	0.0500 (18)	0.048 (2)	0.0393 (19)	0.0186 (17)	0.0110 (15)	0.0044 (17)
C5	0.049 (2)	0.058 (3)	0.061 (3)	0.0101 (19)	0.0095 (17)	−0.003 (2)
C6	0.0400 (18)	0.100 (4)	0.050 (2)	0.025 (2)	−0.0003 (16)	−0.003 (2)
C7	0.058 (2)	0.098 (4)	0.037 (2)	0.053 (3)	0.0016 (16)	0.006 (2)
C8	0.0518 (18)	0.050 (2)	0.0278 (16)	0.0287 (18)	0.0060 (13)	0.0033 (15)
C9	0.0360 (14)	0.0389 (19)	0.0332 (17)	0.0213 (14)	0.0092 (12)	0.0071 (14)
C10	0.0329 (14)	0.0348 (19)	0.0317 (16)	0.0195 (13)	0.0082 (11)	0.0103 (14)
C11	0.0425 (15)	0.0373 (19)	0.0281 (16)	0.0229 (14)	0.0091 (12)	0.0115 (14)
C12	0.0384 (15)	0.0376 (19)	0.0307 (16)	0.0239 (14)	0.0069 (12)	0.0046 (14)
C13	0.0357 (14)	0.0324 (18)	0.0315 (16)	0.0196 (13)	0.0070 (11)	0.0055 (13)
C14	0.0412 (15)	0.0311 (18)	0.0406 (18)	0.0221 (14)	0.0070 (12)	0.0050 (14)
C15	0.0375 (16)	0.039 (2)	0.064 (2)	0.0211 (15)	0.0078 (14)	0.0087 (17)
C16	0.0438 (18)	0.042 (2)	0.080 (3)	0.0235 (17)	0.0197 (18)	0.025 (2)
C17	0.0420 (16)	0.0296 (18)	0.0468 (19)	0.0188 (14)	0.0109 (14)	0.0120 (15)
C18	0.0402 (15)	0.037 (2)	0.0451 (19)	0.0187 (15)	0.0109 (13)	0.0159 (16)
C19	0.0431 (17)	0.043 (2)	0.051 (2)	0.0214 (16)	0.0180 (14)	0.0179 (17)
C20	0.0457 (17)	0.044 (2)	0.054 (2)	0.0232 (16)	0.0111 (15)	0.0234 (18)
C21	0.060 (2)	0.070 (3)	0.049 (2)	0.037 (2)	0.0207 (17)	0.033 (2)
C22	0.0537 (19)	0.061 (3)	0.052 (2)	0.0312 (19)	0.0237 (16)	0.0249 (19)
C23	0.070 (3)	0.103 (4)	0.116 (4)	0.066 (3)	0.043 (3)	0.063 (3)
C24	0.0356 (15)	0.038 (2)	0.057 (2)	0.0193 (14)	0.0119 (14)	0.0158 (17)
C25	0.0439 (17)	0.047 (2)	0.050 (2)	0.0210 (16)	0.0104 (15)	0.0155 (18)
C26	0.057 (2)	0.062 (3)	0.060 (2)	0.032 (2)	0.0248 (18)	0.017 (2)
C27	0.059 (2)	0.064 (3)	0.085 (3)	0.044 (2)	0.032 (2)	0.027 (2)
C28	0.057 (2)	0.080 (3)	0.071 (3)	0.047 (2)	0.0166 (19)	0.031 (2)
C29	0.0485 (18)	0.064 (3)	0.056 (2)	0.0327 (19)	0.0065 (16)	0.013 (2)
C30	0.0435 (16)	0.041 (2)	0.0355 (17)	0.0263 (15)	−0.0031 (13)	0.0077 (15)
C31	0.057 (2)	0.052 (2)	0.045 (2)	0.0381 (19)	0.0046 (15)	0.0036 (17)
C32	0.074 (3)	0.080 (3)	0.059 (3)	0.056 (3)	−0.004 (2)	−0.008 (2)
C33	0.106 (4)	0.064 (3)	0.090 (4)	0.067 (3)	−0.025 (3)	−0.019 (3)
C34	0.093 (3)	0.041 (3)	0.093 (4)	0.039 (3)	−0.020 (3)	0.007 (2)
C35	0.057 (2)	0.037 (2)	0.062 (2)	0.0219 (17)	−0.0066 (17)	0.0126 (18)
C36	0.0404 (16)	0.053 (2)	0.0320 (17)	0.0278 (17)	0.0102 (13)	0.0177 (16)
C37	0.052 (2)	0.097 (4)	0.061 (3)	0.004 (2)	0.024 (2)	0.027 (3)

N1—H1A	0.8600	C17—C18	1.384 (5)
N2—H2	0.8600	C17—N4	1.418 (4)
N3—O4	1.208 (4)	C18—C19	1.382 (4)
N3—O3	1.215 (4)	C18—H18	0.9300
C1—C2	1.358 (5)	C19—C20	1.368 (5)
C1—N1	1.369 (4)	C19—H19	0.9300
C1—H1	0.9300	C20—O6	1.380 (4)
C2—C3	1.431 (5)	C20—C21	1.383 (5)
C2—C9	1.501 (4)	C21—C22	1.375 (5)
C3—C4	1.408 (5)	C21—H21	0.9300
C3—C8	1.417 (4)	C22—H22	0.9300
C4—C5	1.371 (5)	C23—O6	1.417 (5)
C4—H4	0.9300	C23—H23A	0.9600
C5—C6	1.390 (7)	C23—H23B	0.9600
C5—H5	0.9300	C23—H23C	0.9600
C6—C7	1.377 (7)	C24—C25	1.378 (5)
C6—H6	0.9300	C24—C29	1.392 (4)
C7—C8	1.383 (5)	C25—C26	1.380 (5)
C7—H7	0.9300	C25—H25	0.9300
C8—N1	1.362 (5)	C26—C27	1.376 (5)
C9—C10	1.553 (4)	C26—H26	0.9300
C9—H9A	0.9700	C27—C28	1.384 (6)
C9—H9B	0.9700	C27—H27	0.9300
C10—N2	1.459 (4)	C28—C29	1.373 (5)
C10—C36	1.531 (4)	C28—H28	0.9300
C10—C11	1.603 (3)	C29—H29	0.9300
C11—C30	1.511 (4)	C30—C35	1.385 (5)
C11—C12	1.538 (5)	C30—C31	1.395 (5)
C11—H11	0.9800	C31—C32	1.374 (5)
C12—N3	1.511 (4)	C31—H31	0.9300
C12—C13	1.558 (4)	C32—C33	1.365 (8)
C12—H12	0.9800	C32—H32	0.9300
C13—N2	1.451 (4)	C33—C34	1.374 (8)
C13—C14	1.503 (4)	C33—H33	0.9300
C13—H13	0.9800	C34—C35	1.402 (6)
C14—N4	1.478 (4)	C34—H34	0.9300
C14—C15	1.581 (4)	C35—Cl1	1.730 (5)
C14—H14	0.9800	C36—O1	1.197 (4)
C15—C24	1.507 (4)	C36—O2	1.319 (4)
C15—C16	1.523 (5)	C37—O2	1.454 (4)
C15—H15	0.9800	C37—H37A	0.9600
C16—O5	1.206 (5)	C37—H37B	0.9600
C16—N4	1.365 (4)	C37—H37C	0.9600
C17—C22	1.383 (5)
C36—O2—C37	116.4 (3)	C16—C15—C14	84.6 (2)
C20—O6—C23	116.9 (3)	C24—C15—H15	111.2
C8—N1—C1	109.2 (3)	C16—C15—H15	111.2
C8—N1—H1A	125.4	C14—C15—H15	111.2
C1—N1—H1A	125.4	O5—C16—N4	132.5 (3)
C13—N2—C10	105.6 (2)	O5—C16—C15	133.9 (3)
C13—N2—H2	127.2	N4—C16—C15	93.6 (3)
C10—N2—H2	127.2	C22—C17—C18	119.3 (3)
O4—N3—O3	123.6 (3)	C22—C17—N4	118.8 (3)
O4—N3—C12	116.9 (3)	C18—C17—N4	121.8 (3)
O3—N3—C12	119.5 (3)	C19—C18—C17	120.2 (3)
C16—N4—C17	128.4 (3)	C19—C18—H18	119.9
C16—N4—C14	94.5 (3)	C17—C18—H18	119.9
C17—N4—C14	132.7 (3)	C20—C19—C18	120.1 (3)
C2—C1—N1	110.6 (3)	C20—C19—H19	119.9
C2—C1—H1	124.7	C18—C19—H19	119.9
N1—C1—H1	124.7	C19—C20—O6	124.7 (3)
C1—C2—C3	106.0 (3)	C19—C20—C21	119.7 (3)
C1—C2—C9	126.1 (3)	O6—C20—C21	115.6 (3)
C3—C2—C9	127.9 (3)	C22—C21—C20	120.4 (3)
C4—C3—C8	118.1 (3)	C22—C21—H21	119.8
C4—C3—C2	134.6 (3)	C20—C21—H21	119.8
C8—C3—C2	107.3 (3)	C21—C22—C17	120.0 (3)
C5—C4—C3	118.9 (4)	C21—C22—H22	120.0
C5—C4—H4	120.6	C17—C22—H22	120.0
C3—C4—H4	120.6	O6—C23—H23A	109.5
C4—C5—C6	121.8 (4)	O6—C23—H23B	109.5
C4—C5—H5	119.1	H23A—C23—H23B	109.5
C6—C5—H5	119.1	O6—C23—H23C	109.5
C7—C6—C5	121.1 (4)	H23A—C23—H23C	109.5
C7—C6—H6	119.5	H23B—C23—H23C	109.5
C5—C6—H6	119.5	C25—C24—C29	118.1 (3)
C6—C7—C8	117.7 (3)	C25—C24—C15	121.7 (3)
C6—C7—H7	121.2	C29—C24—C15	120.3 (3)
C8—C7—H7	121.2	C24—C25—C26	121.1 (3)
N1—C8—C7	130.5 (3)	C24—C25—H25	119.4
N1—C8—C3	107.0 (3)	C26—C25—H25	119.4
C7—C8—C3	122.5 (4)	C27—C26—C25	120.4 (4)
C2—C9—C10	112.3 (2)	C27—C26—H26	119.8
C2—C9—H9A	109.1	C25—C26—H26	119.8
C10—C9—H9A	109.1	C26—C27—C28	119.1 (3)
C2—C9—H9B	109.1	C26—C27—H27	120.4
C10—C9—H9B	109.1	C28—C27—H27	120.4
H9A—C9—H9B	107.9	C29—C28—C27	120.3 (3)
N2—C10—C36	108.6 (2)	C29—C28—H28	119.8
N2—C10—C9	109.8 (2)	C27—C28—H28	119.8
C36—C10—C9	110.0 (2)	C28—C29—C24	121.0 (4)
N2—C10—C11	105.2 (2)	C28—C29—H29	119.5
C36—C10—C11	108.7 (2)	C24—C29—H29	119.5
C9—C10—C11	114.2 (2)	C35—C30—C31	117.5 (3)
C30—C11—C12	111.5 (2)	C35—C30—C11	121.3 (3)
C30—C11—C10	117.8 (2)	C31—C30—C11	121.2 (3)
C12—C11—C10	103.5 (2)	C32—C31—C30	121.9 (4)
C30—C11—H11	107.8	C32—C31—H31	119.1
C12—C11—H11	107.8	C30—C31—H31	119.1
C10—C11—H11	107.8	C33—C32—C31	120.2 (5)
N3—C12—C11	113.1 (3)	C33—C32—H32	119.9
N3—C12—C13	106.7 (2)	C31—C32—H32	119.9
C11—C12—C13	103.8 (2)	C32—C33—C34	119.7 (4)
N3—C12—H12	111.0	C32—C33—H33	120.2
C11—C12—H12	111.0	C34—C33—H33	120.2
C13—C12—H12	111.0	C33—C34—C35	120.4 (4)
N2—C13—C14	113.7 (2)	C33—C34—H34	119.8
N2—C13—C12	103.5 (2)	C35—C34—H34	119.8
C14—C13—C12	117.3 (2)	C30—C35—C34	120.3 (4)
N2—C13—H13	107.3	C30—C35—Cl1	122.1 (3)
C14—C13—H13	107.3	C34—C35—Cl1	117.5 (4)
C12—C13—H13	107.3	O1—C36—O2	125.4 (3)
N4—C14—C13	115.3 (3)	O1—C36—C10	123.6 (3)
N4—C14—C15	87.1 (2)	O2—C36—C10	111.0 (3)
C13—C14—C15	117.8 (2)	O2—C37—H37A	109.5
N4—C14—H14	111.5	O2—C37—H37B	109.5
C13—C14—H14	111.5	H37A—C37—H37B	109.5
C15—C14—H14	111.5	O2—C37—H37C	109.5
C24—C15—C16	116.4 (3)	H37A—C37—H37C	109.5
C24—C15—C14	119.7 (3)	H37B—C37—H37C	109.5
N1—C1—C2—C3	0.6 (4)	C16—C15—C24—C29	−150.9 (3)
N1—C1—C2—C9	−178.0 (3)	C14—C15—C24—C29	109.9 (4)
C1—C2—C3—C4	−178.8 (3)	C29—C24—C25—C26	−0.2 (5)
C9—C2—C3—C4	−0.3 (6)	C15—C24—C25—C26	179.1 (3)
C1—C2—C3—C8	−0.5 (4)	C24—C25—C26—C27	−0.3 (6)
C9—C2—C3—C8	178.1 (3)	C25—C26—C27—C28	0.1 (6)
C8—C3—C4—C5	−0.3 (5)	C26—C27—C28—C29	0.6 (6)
C2—C3—C4—C5	177.9 (4)	C27—C28—C29—C24	−1.1 (6)
C3—C4—C5—C6	0.6 (6)	C25—C24—C29—C28	0.9 (6)
C4—C5—C6—C7	0.1 (7)	C15—C24—C29—C28	−178.4 (4)
C5—C6—C7—C8	−1.2 (6)	C12—C11—C30—C35	−138.3 (3)
C6—C7—C8—N1	−178.1 (4)	C10—C11—C30—C35	102.2 (3)
C6—C7—C8—C3	1.5 (5)	C12—C11—C30—C31	39.4 (4)
C4—C3—C8—N1	178.9 (3)	C10—C11—C30—C31	−80.1 (4)
C2—C3—C8—N1	0.2 (3)	C35—C30—C31—C32	−0.5 (5)
C4—C3—C8—C7	−0.7 (5)	C11—C30—C31—C32	−178.3 (3)
C2—C3—C8—C7	−179.4 (3)	C30—C31—C32—C33	−0.7 (6)
C1—C2—C9—C10	−76.9 (4)	C31—C32—C33—C34	0.8 (7)
C3—C2—C9—C10	104.8 (4)	C32—C33—C34—C35	0.3 (7)
C2—C9—C10—N2	58.5 (3)	C31—C30—C35—C34	1.6 (5)
C2—C9—C10—C36	−61.0 (3)	C11—C30—C35—C34	179.4 (3)
C2—C9—C10—C11	176.5 (2)	C31—C30—C35—Cl1	−176.2 (2)
N2—C10—C11—C30	134.8 (3)	C11—C30—C35—Cl1	1.6 (5)
C36—C10—C11—C30	−109.0 (3)	C33—C34—C35—C30	−1.5 (6)
C9—C10—C11—C30	14.2 (4)	C33—C34—C35—Cl1	176.4 (4)
N2—C10—C11—C12	11.2 (3)	N2—C10—C36—O1	16.0 (4)
C36—C10—C11—C12	127.4 (3)	C9—C10—C36—O1	136.2 (3)
C9—C10—C11—C12	−109.4 (3)	C11—C10—C36—O1	−98.0 (3)
C30—C11—C12—N3	131.4 (2)	N2—C10—C36—O2	−165.9 (2)
C10—C11—C12—N3	−101.0 (2)	C9—C10—C36—O2	−45.6 (3)
C30—C11—C12—C13	−113.4 (3)	C11—C10—C36—O2	80.1 (3)
C10—C11—C12—C13	14.3 (3)	C7—C8—N1—C1	179.7 (4)
N3—C12—C13—N2	84.1 (3)	C3—C8—N1—C1	0.1 (4)
C11—C12—C13—N2	−35.6 (3)	C2—C1—N1—C8	−0.4 (4)
N3—C12—C13—C14	−42.0 (3)	C14—C13—N2—C10	172.5 (2)
C11—C12—C13—C14	−161.7 (2)	C12—C13—N2—C10	44.1 (3)
N2—C13—C14—N4	72.2 (3)	C36—C10—N2—C13	−150.8 (2)
C12—C13—C14—N4	−166.9 (2)	C9—C10—N2—C13	88.8 (2)
N2—C13—C14—C15	172.8 (3)	C11—C10—N2—C13	−34.6 (3)
C12—C13—C14—C15	−66.3 (4)	C11—C12—N3—O4	−157.2 (3)
N4—C14—C15—C24	113.5 (3)	C13—C12—N3—O4	89.3 (3)
C13—C14—C15—C24	−3.7 (5)	C11—C12—N3—O3	25.3 (4)
N4—C14—C15—C16	−3.9 (3)	C13—C12—N3—O3	−88.2 (3)
C13—C14—C15—C16	−121.1 (3)	O5—C16—N4—C17	16.9 (7)
C24—C15—C16—O5	63.8 (6)	C15—C16—N4—C17	−163.0 (3)
C14—C15—C16—O5	−175.6 (5)	O5—C16—N4—C14	175.3 (5)
C24—C15—C16—N4	−116.3 (3)	C15—C16—N4—C14	−4.5 (3)
C14—C15—C16—N4	4.2 (3)	C22—C17—N4—C16	−36.5 (5)
C22—C17—C18—C19	2.4 (5)	C18—C17—N4—C16	140.0 (4)
N4—C17—C18—C19	−174.1 (3)	C22—C17—N4—C14	173.4 (3)
C17—C18—C19—C20	0.8 (6)	C18—C17—N4—C14	−10.1 (6)
C18—C19—C20—O6	176.6 (4)	C13—C14—N4—C16	123.8 (3)
C18—C19—C20—C21	−3.5 (6)	C15—C14—N4—C16	4.4 (3)
C19—C20—C21—C22	3.2 (6)	C13—C14—N4—C17	−79.3 (4)
O6—C20—C21—C22	−176.9 (4)	C15—C14—N4—C17	161.3 (4)
C20—C21—C22—C17	−0.1 (7)	O1—C36—O2—C37	−1.3 (5)
C18—C17—C22—C21	−2.7 (6)	C10—C36—O2—C37	−179.4 (3)
N4—C17—C22—C21	173.9 (4)	C19—C20—O6—C23	−4.1 (6)
C16—C15—C24—C25	29.9 (5)	C21—C20—O6—C23	176.0 (4)
C14—C15—C24—C25	−69.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Cl1	0.98	2.57	3.095 (4)	114
C11—H11···O3	0.98	2.37	2.786 (4)	105
C22—H22···O5	0.93	2.59	3.080 (6)	113
C14—H14···O4i	0.98	2.53	3.443 (5)	154
C34—H34···O4ii	0.93	2.59	3.414 (6)	148
N1—H1A···O6iii	0.86	2.14	2.982 (5)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯Cl1	0.98	2.57	3.095 (4)	114
C11—H11⋯O3	0.98	2.37	2.786 (4)	105
C22—H22⋯O5	0.93	2.59	3.080 (6)	113
C14—H14⋯O4i	0.98	2.53	3.443 (5)	154
C34—H34⋯O4ii	0.93	2.59	3.414 (6)	148
N1—H1A⋯O6iii	0.86	2.14	2.982 (5)	167

Symmetry codes: (i) ; (ii) ; (iii) .