Ethyl 1-(4-chloro-phen-yl)-3-[1-(4-meth-oxy-phen-yl)-4-oxo-3-phenyl-azetidin-2-yl]-2-nitro-2,3,10,10a-tetra-hydro-1H,5H-pyr-rolo[1,2-b]isoquinoline-10a-carboxyl-ate.

In the title compound, C(37)H(34)ClN(3)O(6), the pyrrolidine and piperidine rings adopt envelope and boat conformations, respectively. The β-lactam ring is planar and forms dihedral angles of 21.3 (2) and 73.9 (2)°, respectively, with the attached methoxy-phenyl and phenyl rings. Intra-molecular C-H⋯O and C-H⋯N hydrogen bonds are observed. Centrosym-metrically related mol-ecules are linked together by weak C-H⋯O hydrogen bonds to form dimers.

Related literature

For the biological properties of β-lactam derivatives, see: Borthwick et al. (1998 ▶); Brakhage (1998 ▶); Burnett (1994 ▶); Han et al. (1995 ▶); Vaccaro & Davis (1998 ▶); Vaccaro et al. (1998 ▶). For puckering and asymmetry parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C37H34ClN3O6

M = 652.12

Monoclinic,

a = 9.1723 (2) Å

b = 18.0452 (4) Å

c = 19.7475 (5) Å

β = 100.638 (1)°

V = 3212.35 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.17 mm−1

T = 293 (2) K

0.22 × 0.20 × 0.17 mm

Data collection

Bruker kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.963, T max = 0.971

30325 measured reflections

5582 independent reflections

3760 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.135

S = 1.02

5582 reflections

426 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808030961/ci2676sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030961/ci2676Isup2.hkl

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

C37H34ClN3O6	F(000) = 1368
Mr = 652.12	Dx = 1.348 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5002 reflections
a = 9.1723 (2) Å	θ = 1.5–24.9°
b = 18.0452 (4) Å	µ = 0.17 mm−1
c = 19.7475 (5) Å	T = 293 K
β = 100.638 (1)°	Block, colourless
V = 3212.35 (13) Å3	0.22 × 0.20 × 0.17 mm
Z = 4

Bruker kappa APEXII area-detector diffractometer	5582 independent reflections
Radiation source: fine-focus sealed tube	3760 reflections with I > 2σ(I)
graphite	Rint = 0.034
ω and φ scans	θmax = 24.9°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −10→10
Tmin = 0.963, Tmax = 0.971	k = −20→21
30325 measured reflections	l = −23→23

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0537P)2 + 1.5127P] where P = (Fo2 + 2Fc2)/3
5582 reflections	(Δ/σ)max = 0.001
426 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	0.26960 (11)	0.43479 (5)	0.60642 (4)	0.0979 (3)
O1	−0.1144 (2)	0.31964 (12)	0.15686 (11)	0.0870 (6)
O2	−0.2380 (2)	0.31467 (12)	0.24445 (12)	0.0914 (7)
O3	−0.2459 (3)	0.47487 (16)	0.18822 (18)	0.1215 (11)
O4	−0.2416 (4)	0.58070 (18)	0.23474 (14)	0.1523 (14)
O5	0.3329 (2)	0.63293 (11)	0.11354 (11)	0.0839 (6)
O6	0.2021 (2)	0.31726 (12)	−0.07279 (10)	0.0823 (6)
N1	0.08498 (19)	0.41518 (10)	0.21858 (10)	0.0468 (5)
C2	0.2354 (3)	0.38685 (14)	0.21800 (13)	0.0556 (6)
H2A	0.2891	0.4229	0.1957	0.067*
H2B	0.2280	0.3416	0.1911	0.067*
C3	0.3207 (3)	0.37143 (13)	0.28843 (13)	0.0537 (6)
C4	0.4641 (3)	0.39488 (18)	0.31274 (17)	0.0771 (8)
H4	0.5137	0.4230	0.2847	0.093*
C5	0.5336 (3)	0.3767 (2)	0.3782 (2)	0.0940 (10)
H5	0.6295	0.3934	0.3947	0.113*
C6	0.4625 (4)	0.33415 (19)	0.41941 (17)	0.0836 (9)
H6	0.5113	0.3209	0.4633	0.100*
C7	0.3198 (3)	0.31095 (14)	0.39631 (14)	0.0644 (7)
H7	0.2714	0.2824	0.4246	0.077*
C8	0.2481 (3)	0.33003 (12)	0.33104 (13)	0.0499 (6)
C9	0.0928 (3)	0.30842 (12)	0.30105 (13)	0.0547 (6)
H9A	0.0441	0.2909	0.3377	0.066*
H9B	0.0945	0.2678	0.2690	0.066*
C10	0.0017 (2)	0.37342 (12)	0.26295 (12)	0.0487 (6)
C11	−0.0500 (3)	0.43205 (12)	0.31170 (13)	0.0513 (6)
H11	−0.1545	0.4222	0.3132	0.062*
C12	−0.0423 (3)	0.50536 (13)	0.27378 (13)	0.0551 (6)
H12	−0.0162	0.5457	0.3070	0.066*
C13	0.0807 (3)	0.49450 (12)	0.23229 (12)	0.0479 (5)
H13	0.1747	0.5079	0.2621	0.058*
C14	−0.1333 (3)	0.33509 (15)	0.22050 (16)	0.0654 (7)
C15	−0.2295 (5)	0.2774 (2)	0.1122 (2)	0.1293 (16)
H15A	−0.1831	0.2395	0.0886	0.155*
H15B	−0.2911	0.2528	0.1403	0.155*
C16	−0.3162 (5)	0.3200 (3)	0.0650 (2)	0.163 (2)
H16A	−0.3704	0.3544	0.0880	0.245*
H16B	−0.3846	0.2891	0.0348	0.245*
H16C	−0.2554	0.3467	0.0387	0.245*
C17	0.0339 (3)	0.43451 (12)	0.38492 (13)	0.0522 (6)
C18	−0.0165 (3)	0.39231 (14)	0.43459 (14)	0.0624 (7)
H18	−0.1011	0.3634	0.4220	0.075*
C19	0.0560 (3)	0.39233 (16)	0.50219 (15)	0.0717 (8)
H19	0.0207	0.3635	0.5348	0.086*
C20	0.1801 (3)	0.43493 (16)	0.52118 (14)	0.0677 (8)
C21	0.2316 (3)	0.47828 (15)	0.47366 (15)	0.0696 (7)
H21	0.3153	0.5077	0.4869	0.083*
C22	0.1586 (3)	0.47789 (14)	0.40612 (13)	0.0610 (7)
H22	0.1938	0.5074	0.3740	0.073*
N23	−0.1895 (3)	0.52072 (17)	0.22867 (14)	0.0772 (8)
C24	0.0636 (3)	0.54308 (12)	0.16801 (12)	0.0512 (6)
H24	−0.0372	0.5412	0.1409	0.061*
C25	0.1223 (3)	0.62490 (13)	0.18009 (13)	0.0559 (6)
H25	0.0496	0.6593	0.1546	0.067*
C26	0.2339 (3)	0.60255 (14)	0.13526 (13)	0.0611 (7)
N27	0.1771 (2)	0.53255 (11)	0.12491 (10)	0.0555 (5)
C28	0.1739 (3)	0.65324 (12)	0.25172 (13)	0.0547 (6)
C29	0.3113 (3)	0.63541 (14)	0.28979 (16)	0.0678 (7)
H29	0.3770	0.6073	0.2698	0.081*
C30	0.3525 (4)	0.65882 (17)	0.35720 (18)	0.0828 (9)
H30	0.4448	0.6456	0.3823	0.099*
C31	0.2596 (4)	0.70088 (18)	0.38705 (18)	0.0861 (9)
H31	0.2877	0.7163	0.4325	0.103*
C32	0.1253 (4)	0.72025 (16)	0.35001 (18)	0.0813 (9)
H32	0.0616	0.7494	0.3703	0.098*
C33	0.0822 (3)	0.69735 (14)	0.28273 (16)	0.0665 (7)
H33	−0.0097	0.7118	0.2579	0.080*
C34	0.1861 (3)	0.47852 (13)	0.07403 (12)	0.0533 (6)
C35	0.3076 (3)	0.47553 (16)	0.04257 (15)	0.0700 (8)
H35	0.3843	0.5094	0.0547	0.084*
C36	0.3168 (3)	0.42258 (16)	−0.00697 (15)	0.0725 (8)
H36	0.3991	0.4213	−0.0283	0.087*
C37	0.2053 (3)	0.37216 (15)	−0.02476 (13)	0.0596 (6)
C38	0.0838 (3)	0.37514 (15)	0.00705 (13)	0.0612 (7)
H38	0.0073	0.3411	−0.0050	0.073*
C39	0.0741 (3)	0.42744 (14)	0.05597 (13)	0.0573 (6)
H39	−0.0084	0.4286	0.0772	0.069*
C40	0.3268 (3)	0.30843 (19)	−0.10496 (16)	0.0824 (9)
H40A	0.3477	0.3545	−0.1256	0.124*
H40B	0.3062	0.2710	−0.1399	0.124*
H40C	0.4112	0.2939	−0.0712	0.124*

	U11	U22	U33	U12	U13	U23
Cl1	0.1261 (7)	0.1070 (6)	0.0593 (5)	0.0466 (5)	0.0135 (5)	−0.0010 (4)
O1	0.0823 (14)	0.1021 (16)	0.0680 (14)	−0.0362 (12)	−0.0090 (11)	0.0012 (11)
O2	0.0641 (13)	0.0896 (15)	0.1228 (19)	−0.0263 (11)	0.0235 (12)	0.0104 (13)
O3	0.0639 (15)	0.0989 (19)	0.183 (3)	−0.0030 (13)	−0.0253 (17)	0.0309 (19)
O4	0.183 (3)	0.162 (3)	0.107 (2)	0.128 (2)	0.0138 (19)	0.0210 (18)
O5	0.0955 (15)	0.0691 (12)	0.0985 (16)	−0.0293 (11)	0.0479 (13)	−0.0002 (11)
O6	0.0805 (13)	0.0942 (15)	0.0781 (14)	−0.0059 (11)	0.0301 (11)	−0.0264 (11)
N1	0.0446 (11)	0.0440 (10)	0.0542 (12)	0.0015 (8)	0.0153 (9)	0.0028 (8)
C2	0.0516 (14)	0.0588 (14)	0.0607 (16)	0.0085 (11)	0.0215 (12)	−0.0004 (12)
C3	0.0449 (14)	0.0546 (14)	0.0628 (16)	0.0097 (11)	0.0132 (12)	−0.0047 (12)
C4	0.0477 (16)	0.090 (2)	0.096 (2)	0.0049 (14)	0.0180 (16)	0.0048 (17)
C5	0.0507 (18)	0.113 (3)	0.109 (3)	0.0087 (18)	−0.0078 (19)	−0.001 (2)
C6	0.075 (2)	0.094 (2)	0.073 (2)	0.0268 (18)	−0.0099 (17)	−0.0029 (18)
C7	0.0673 (18)	0.0575 (15)	0.0676 (18)	0.0192 (13)	0.0107 (14)	0.0045 (13)
C8	0.0523 (14)	0.0401 (12)	0.0574 (15)	0.0105 (10)	0.0102 (12)	−0.0025 (11)
C9	0.0590 (15)	0.0438 (13)	0.0624 (16)	0.0010 (11)	0.0135 (12)	0.0045 (11)
C10	0.0460 (13)	0.0449 (12)	0.0570 (15)	−0.0022 (10)	0.0147 (11)	0.0061 (10)
C11	0.0448 (13)	0.0510 (13)	0.0624 (16)	0.0063 (10)	0.0210 (12)	0.0128 (11)
C12	0.0566 (15)	0.0506 (13)	0.0628 (16)	0.0099 (11)	0.0235 (12)	0.0121 (11)
C13	0.0506 (13)	0.0434 (12)	0.0524 (14)	0.0012 (10)	0.0165 (11)	0.0047 (10)
C14	0.0532 (16)	0.0605 (16)	0.080 (2)	−0.0077 (12)	0.0061 (14)	0.0148 (14)
C15	0.116 (3)	0.118 (3)	0.126 (3)	−0.056 (3)	−0.049 (3)	0.015 (3)
C16	0.147 (4)	0.197 (5)	0.117 (4)	−0.089 (4)	−0.054 (3)	0.056 (4)
C17	0.0563 (15)	0.0456 (13)	0.0607 (16)	0.0136 (11)	0.0268 (12)	0.0062 (11)
C18	0.0636 (16)	0.0617 (16)	0.0685 (18)	0.0128 (12)	0.0291 (14)	0.0159 (13)
C19	0.085 (2)	0.0726 (18)	0.0664 (19)	0.0274 (16)	0.0365 (17)	0.0206 (15)
C20	0.084 (2)	0.0662 (17)	0.0564 (17)	0.0298 (16)	0.0217 (15)	0.0001 (14)
C21	0.081 (2)	0.0640 (17)	0.0662 (19)	0.0074 (14)	0.0208 (16)	−0.0104 (14)
C22	0.0775 (18)	0.0541 (15)	0.0570 (17)	0.0032 (13)	0.0275 (14)	−0.0006 (12)
N23	0.0689 (17)	0.0873 (19)	0.0842 (19)	0.0343 (15)	0.0372 (15)	0.0408 (15)
C24	0.0510 (14)	0.0512 (13)	0.0535 (14)	−0.0018 (10)	0.0155 (11)	0.0061 (11)
C25	0.0631 (16)	0.0464 (13)	0.0597 (16)	−0.0005 (11)	0.0150 (13)	0.0100 (11)
C26	0.0712 (17)	0.0539 (15)	0.0612 (16)	−0.0088 (13)	0.0204 (14)	0.0096 (12)
N27	0.0630 (13)	0.0520 (12)	0.0564 (13)	−0.0118 (9)	0.0240 (10)	0.0015 (9)
C28	0.0599 (16)	0.0421 (13)	0.0632 (16)	−0.0049 (11)	0.0139 (13)	0.0076 (11)
C29	0.0655 (18)	0.0538 (15)	0.084 (2)	−0.0015 (13)	0.0131 (16)	0.0007 (14)
C30	0.078 (2)	0.0727 (19)	0.089 (2)	−0.0049 (16)	−0.0078 (18)	−0.0006 (17)
C31	0.103 (3)	0.075 (2)	0.077 (2)	−0.0136 (19)	0.006 (2)	−0.0069 (17)
C32	0.098 (2)	0.0653 (18)	0.089 (2)	−0.0054 (17)	0.037 (2)	−0.0132 (16)
C33	0.0673 (17)	0.0526 (15)	0.082 (2)	0.0022 (13)	0.0190 (15)	0.0036 (14)
C34	0.0600 (15)	0.0546 (14)	0.0485 (14)	−0.0056 (11)	0.0181 (12)	0.0076 (11)
C35	0.0649 (17)	0.0724 (18)	0.079 (2)	−0.0210 (14)	0.0286 (15)	−0.0059 (15)
C36	0.0656 (18)	0.082 (2)	0.079 (2)	−0.0086 (15)	0.0366 (15)	−0.0050 (16)
C37	0.0623 (16)	0.0672 (16)	0.0516 (15)	−0.0007 (13)	0.0166 (13)	−0.0013 (12)
C38	0.0623 (16)	0.0690 (16)	0.0545 (15)	−0.0145 (13)	0.0163 (13)	−0.0038 (13)
C39	0.0551 (15)	0.0685 (16)	0.0522 (15)	−0.0111 (12)	0.0203 (12)	0.0007 (12)
C40	0.079 (2)	0.099 (2)	0.0722 (19)	0.0267 (17)	0.0224 (16)	−0.0084 (17)

Cl1—C20	1.731 (3)	C16—H16C	0.96
O1—C14	1.329 (3)	C17—C22	1.385 (4)
O1—C15	1.460 (4)	C17—C18	1.387 (3)
O2—C14	1.204 (3)	C18—C19	1.377 (4)
O3—N23	1.199 (4)	C18—H18	0.93
O4—N23	1.198 (3)	C19—C20	1.368 (4)
O5—C26	1.205 (3)	C19—H19	0.93
O6—C37	1.368 (3)	C20—C21	1.371 (4)
O6—C40	1.416 (3)	C21—C22	1.378 (4)
N1—C13	1.459 (3)	C21—H21	0.93
N1—C10	1.472 (3)	C22—H22	0.93
N1—C2	1.473 (3)	C24—N27	1.474 (3)
C2—C3	1.491 (3)	C24—C25	1.575 (3)
C2—H2A	0.97	C24—H24	0.98
C2—H2B	0.97	C25—C28	1.496 (3)
C3—C4	1.381 (4)	C25—C26	1.526 (4)
C3—C8	1.384 (3)	C25—H25	0.98
C4—C5	1.372 (4)	C26—N27	1.367 (3)
C4—H4	0.93	N27—C34	1.413 (3)
C5—C6	1.368 (5)	C28—C33	1.381 (4)
C5—H5	0.93	C28—C29	1.381 (4)
C6—C7	1.370 (4)	C29—C30	1.381 (4)
C6—H6	0.93	C29—H29	0.93
C7—C8	1.378 (3)	C30—C31	1.354 (5)
C7—H7	0.93	C30—H30	0.93
C8—C9	1.490 (3)	C31—C32	1.357 (4)
C9—C10	1.552 (3)	C31—H31	0.93
C9—H9A	0.97	C32—C33	1.378 (4)
C9—H9B	0.97	C32—H32	0.93
C10—C14	1.527 (4)	C33—H33	0.93
C10—C11	1.562 (3)	C34—C35	1.374 (3)
C11—C17	1.508 (3)	C34—C39	1.377 (3)
C11—C12	1.528 (3)	C35—C36	1.381 (4)
C11—H11	0.98	C35—H35	0.93
C12—N23	1.500 (4)	C36—C37	1.365 (4)
C12—C13	1.524 (3)	C36—H36	0.93
C12—H12	0.98	C37—C38	1.378 (3)
C13—C24	1.527 (3)	C38—C39	1.365 (3)
C13—H13	0.98	C38—H38	0.93
C15—C16	1.347 (5)	C39—H39	0.93
C15—H15A	0.97	C40—H40A	0.96
C15—H15B	0.97	C40—H40B	0.96
C16—H16A	0.96	C40—H40C	0.96
C16—H16B	0.96
C14—O1—C15	118.3 (3)	C19—C18—H18	119.3
C37—O6—C40	118.5 (2)	C17—C18—H18	119.3
C13—N1—C10	110.93 (17)	C20—C19—C18	119.6 (3)
C13—N1—C2	113.53 (18)	C20—C19—H19	120.2
C10—N1—C2	114.62 (17)	C18—C19—H19	120.2
N1—C2—C3	112.88 (19)	C19—C20—C21	120.5 (3)
N1—C2—H2A	109.0	C19—C20—Cl1	119.1 (2)
C3—C2—H2A	109.0	C21—C20—Cl1	120.3 (3)
N1—C2—H2B	109.0	C20—C21—C22	119.5 (3)
C3—C2—H2B	109.0	C20—C21—H21	120.3
H2A—C2—H2B	107.8	C22—C21—H21	120.3
C4—C3—C8	119.2 (3)	C21—C22—C17	121.5 (2)
C4—C3—C2	124.7 (2)	C21—C22—H22	119.3
C8—C3—C2	116.0 (2)	C17—C22—H22	119.3
C5—C4—C3	120.1 (3)	O4—N23—O3	124.0 (3)
C5—C4—H4	120.0	O4—N23—C12	116.1 (3)
C3—C4—H4	120.0	O3—N23—C12	119.9 (2)
C6—C5—C4	120.3 (3)	N27—C24—C13	115.53 (19)
C6—C5—H5	119.8	N27—C24—C25	87.13 (16)
C4—C5—H5	119.8	C13—C24—C25	115.6 (2)
C5—C6—C7	120.3 (3)	N27—C24—H24	112.1
C5—C6—H6	119.8	C13—C24—H24	112.1
C7—C6—H6	119.8	C25—C24—H24	112.1
C6—C7—C8	119.8 (3)	C28—C25—C26	120.7 (2)
C6—C7—H7	120.1	C28—C25—C24	120.22 (19)
C8—C7—H7	120.1	C26—C25—C24	84.93 (18)
C7—C8—C3	120.2 (2)	C28—C25—H25	109.6
C7—C8—C9	124.2 (2)	C26—C25—H25	109.6
C3—C8—C9	115.6 (2)	C24—C25—H25	109.6
C8—C9—C10	112.61 (18)	O5—C26—N27	131.2 (3)
C8—C9—H9A	109.1	O5—C26—C25	135.7 (2)
C10—C9—H9A	109.1	N27—C26—C25	93.04 (19)
C8—C9—H9B	109.1	C26—N27—C34	132.3 (2)
C10—C9—H9B	109.1	C26—N27—C24	94.87 (18)
H9A—C9—H9B	107.8	C34—N27—C24	129.76 (19)
N1—C10—C14	111.3 (2)	C33—C28—C29	117.6 (3)
N1—C10—C9	112.56 (18)	C33—C28—C25	120.3 (2)
C14—C10—C9	103.48 (18)	C29—C28—C25	122.2 (2)
N1—C10—C11	105.68 (17)	C30—C29—C28	120.8 (3)
C14—C10—C11	109.7 (2)	C30—C29—H29	119.6
C9—C10—C11	114.24 (19)	C28—C29—H29	119.6
C17—C11—C12	112.5 (2)	C31—C30—C29	120.6 (3)
C17—C11—C10	116.85 (18)	C31—C30—H30	119.7
C12—C11—C10	103.73 (18)	C29—C30—H30	119.7
C17—C11—H11	107.8	C30—C31—C32	119.4 (3)
C12—C11—H11	107.8	C30—C31—H31	120.3
C10—C11—H11	107.8	C32—C31—H31	120.3
N23—C12—C13	112.3 (2)	C31—C32—C33	120.9 (3)
N23—C12—C11	109.4 (2)	C31—C32—H32	119.6
C13—C12—C11	104.96 (18)	C33—C32—H32	119.6
N23—C12—H12	110.0	C32—C33—C28	120.7 (3)
C13—C12—H12	110.0	C32—C33—H33	119.7
C11—C12—H12	110.0	C28—C33—H33	119.7
N1—C13—C12	105.89 (17)	C35—C34—C39	119.0 (2)
N1—C13—C24	114.29 (19)	C35—C34—N27	120.5 (2)
C12—C13—C24	113.61 (18)	C39—C34—N27	120.5 (2)
N1—C13—H13	107.6	C34—C35—C36	120.5 (2)
C12—C13—H13	107.6	C34—C35—H35	119.7
C24—C13—H13	107.6	C36—C35—H35	119.7
O2—C14—O1	124.0 (3)	C37—C36—C35	120.2 (2)
O2—C14—C10	123.2 (3)	C37—C36—H36	119.9
O1—C14—C10	112.3 (2)	C35—C36—H36	119.9
C16—C15—O1	112.9 (3)	C36—C37—O6	125.5 (2)
C16—C15—H15A	109.0	C36—C37—C38	119.1 (2)
O1—C15—H15A	109.0	O6—C37—C38	115.4 (2)
C16—C15—H15B	109.0	C39—C38—C37	120.9 (2)
O1—C15—H15B	109.0	C39—C38—H38	119.6
H15A—C15—H15B	107.8	C37—C38—H38	119.6
C15—C16—H16A	109.5	C38—C39—C34	120.2 (2)
C15—C16—H16B	109.5	C38—C39—H39	119.9
H16A—C16—H16B	109.5	C34—C39—H39	119.9
C15—C16—H16C	109.5	O6—C40—H40A	109.5
H16A—C16—H16C	109.5	O6—C40—H40B	109.5
H16B—C16—H16C	109.5	H40A—C40—H40B	109.5
C22—C17—C18	117.5 (2)	O6—C40—H40C	109.5
C22—C17—C11	123.6 (2)	H40A—C40—H40C	109.5
C18—C17—C11	119.0 (2)	H40B—C40—H40C	109.5
C19—C18—C17	121.4 (3)
C13—N1—C2—C3	82.0 (2)	C18—C19—C20—C21	0.9 (4)
C10—N1—C2—C3	−46.9 (3)	C18—C19—C20—Cl1	179.67 (19)
N1—C2—C3—C4	−131.6 (3)	C19—C20—C21—C22	−0.9 (4)
N1—C2—C3—C8	48.9 (3)	Cl1—C20—C21—C22	−179.73 (19)
C8—C3—C4—C5	0.5 (4)	C20—C21—C22—C17	−0.1 (4)
C2—C3—C4—C5	−179.0 (3)	C18—C17—C22—C21	1.1 (3)
C3—C4—C5—C6	1.2 (5)	C11—C17—C22—C21	−180.0 (2)
C4—C5—C6—C7	−1.8 (5)	C13—C12—N23—O4	−115.0 (3)
C5—C6—C7—C8	0.6 (4)	C11—C12—N23—O4	128.8 (3)
C6—C7—C8—C3	1.1 (4)	C13—C12—N23—O3	63.0 (3)
C6—C7—C8—C9	−179.4 (2)	C11—C12—N23—O3	−53.2 (3)
C4—C3—C8—C7	−1.6 (3)	N1—C13—C24—N27	−56.2 (3)
C2—C3—C8—C7	177.9 (2)	C12—C13—C24—N27	−177.9 (2)
C4—C3—C8—C9	178.8 (2)	N1—C13—C24—C25	−155.91 (19)
C2—C3—C8—C9	−1.6 (3)	C12—C13—C24—C25	82.4 (3)
C7—C8—C9—C10	135.8 (2)	N27—C24—C25—C28	−123.9 (2)
C3—C8—C9—C10	−44.7 (3)	C13—C24—C25—C28	−6.9 (3)
C13—N1—C10—C14	115.2 (2)	N27—C24—C25—C26	−1.17 (17)
C2—N1—C10—C14	−114.6 (2)	C13—C24—C25—C26	115.9 (2)
C13—N1—C10—C9	−129.2 (2)	C28—C25—C26—O5	−58.7 (4)
C2—N1—C10—C9	1.0 (3)	C24—C25—C26—O5	179.0 (3)
C13—N1—C10—C11	−3.9 (2)	C28—C25—C26—N27	123.6 (2)
C2—N1—C10—C11	126.3 (2)	C24—C25—C26—N27	1.27 (19)
C8—C9—C10—N1	44.5 (3)	O5—C26—N27—C34	−18.2 (5)
C8—C9—C10—C14	164.7 (2)	C25—C26—N27—C34	159.6 (3)
C8—C9—C10—C11	−76.0 (2)	O5—C26—N27—C24	−179.2 (3)
N1—C10—C11—C17	−103.8 (2)	C25—C26—N27—C24	−1.4 (2)
C14—C10—C11—C17	136.2 (2)	C13—C24—N27—C26	−115.8 (2)
C9—C10—C11—C17	20.5 (3)	C25—C24—N27—C26	1.31 (19)
N1—C10—C11—C12	20.6 (2)	C13—C24—N27—C34	82.5 (3)
C14—C10—C11—C12	−99.4 (2)	C25—C24—N27—C34	−160.4 (2)
C9—C10—C11—C12	144.93 (19)	C26—C25—C28—C33	156.5 (2)
C17—C11—C12—N23	−141.4 (2)	C24—C25—C28—C33	−100.4 (3)
C10—C11—C12—N23	91.4 (2)	C26—C25—C28—C29	−25.0 (3)
C17—C11—C12—C13	97.9 (2)	C24—C25—C28—C29	78.0 (3)
C10—C11—C12—C13	−29.3 (2)	C33—C28—C29—C30	2.3 (4)
C10—N1—C13—C12	−14.7 (2)	C25—C28—C29—C30	−176.2 (2)
C2—N1—C13—C12	−145.46 (19)	C28—C29—C30—C31	−1.1 (5)
C10—N1—C13—C24	−140.51 (19)	C29—C30—C31—C32	−0.3 (5)
C2—N1—C13—C24	88.7 (2)	C30—C31—C32—C33	0.4 (5)
N23—C12—C13—N1	−91.3 (2)	C31—C32—C33—C28	0.9 (4)
C11—C12—C13—N1	27.5 (2)	C29—C28—C33—C32	−2.2 (4)
N23—C12—C13—C24	35.0 (3)	C25—C28—C33—C32	176.3 (2)
C11—C12—C13—C24	153.8 (2)	C26—N27—C34—C35	29.3 (4)
C15—O1—C14—O2	2.1 (4)	C24—N27—C34—C35	−175.7 (2)
C15—O1—C14—C10	175.0 (3)	C26—N27—C34—C39	−151.7 (3)
N1—C10—C14—O2	−159.7 (2)	C24—N27—C34—C39	3.3 (4)
C9—C10—C14—O2	79.2 (3)	C39—C34—C35—C36	0.7 (4)
C11—C10—C14—O2	−43.1 (3)	N27—C34—C35—C36	179.7 (3)
N1—C10—C14—O1	27.3 (3)	C34—C35—C36—C37	−0.6 (5)
C9—C10—C14—O1	−93.8 (2)	C35—C36—C37—O6	−179.9 (3)
C11—C10—C14—O1	143.9 (2)	C35—C36—C37—C38	0.3 (4)
C14—O1—C15—C16	103.2 (5)	C40—O6—C37—C36	3.4 (4)
C12—C11—C17—C22	−30.5 (3)	C40—O6—C37—C38	−176.7 (2)
C10—C11—C17—C22	89.3 (3)	C36—C37—C38—C39	−0.2 (4)
C12—C11—C17—C18	148.4 (2)	O6—C37—C38—C39	179.9 (2)
C10—C11—C17—C18	−91.8 (2)	C37—C38—C39—C34	0.4 (4)
C22—C17—C18—C19	−1.2 (3)	C35—C34—C39—C38	−0.6 (4)
C11—C17—C18—C19	179.8 (2)	N27—C34—C39—C38	−179.6 (2)
C17—C18—C19—C20	0.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···N27	0.97	2.53	3.196 (3)	126
C24—H24···O3	0.98	2.58	3.186 (3)	121
C25—H25···O6i	0.98	2.60	3.479 (3)	150
C35—H35···O5	0.93	2.60	3.157 (3)	119
C40—H40A···O4i	0.96	2.49	3.232 (4)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯N27	0.97	2.53	3.196 (3)	126
C24—H24⋯O3	0.98	2.58	3.186 (3)	121
C25—H25⋯O6i	0.98	2.60	3.479 (3)	150
C35—H35⋯O5	0.93	2.60	3.157 (3)	119
C40—H40A⋯O4i	0.96	2.49	3.232 (4)	134

Symmetry code: (i) .