5-Chloro-5''-(4-chloro-benzyl-idene)-4'-(4-chloro-phen-yl)-1''-ethyl-1'-methyl-dispiro-[indoline-3,2'-pyrrolidine-3',3''-piperidine]-2,4''-dione.

Two spiro links are found in the title compound, C31H28Cl3N3O2, one connecting the piperidine and pyrrolidine rings, and the other connecting the pyrrolidine ring and indole residue. The piperidine ring adopts a half-chair conformation, in which the C atom connected to the spiro-C atom lies 0.741 (3) Å out of the plane of the remaining five atoms (r.m.s. deviation = 0.053 Å). The pyrrolidine ring has an envelope conformation with the flap atom being the methyl-ene C atom. Centrosymmetric eight-membered {⋯HNCO}2 amide dimers are the most significant feature of the crystal packing. These are connected into layers parallel to (-120) by C-H⋯O and π-π inter-actions between pyrrolidine-bound benzene rings [inter-centroid distance = 3.8348 (15) Å]. Slipped face-to-face inter-actions between the edges of pyrrolidine-bound benzene [shortest C⋯C separation = 3.484 (4) Å] connect the layers into a three-dimensional architecture.

Related literature

For the biological activity of related spiro­pyrrolidine analogues, see: Girgis et al. (2012 ▶); Kumar et al. (2008 ▶). For related structural studies, see: Farag et al. (2013 ▶). For the synthesis of the precursor mol­ecule, see Al-Omary et al. (2012 ▶).

Experimental

Crystal data

C31H28Cl3N3O2

M = 580.91

Triclinic,

a = 11.1901 (2) Å

b = 11.6434 (3) Å

c = 12.4270 (3) Å

α = 99.477 (2)°

β = 90.235 (2)°

γ = 114.893 (1)°

V = 1443.77 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.35 mm−1

T = 293 K

1.02 × 0.53 × 0.37 mm

Data collection

Nonius 590 KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.880, T max = 0.994

11344 measured reflections

6482 independent reflections

4260 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.160

S = 1.00

6482 reflections

354 parameters

H-atom parameters constrained

Δρmax = 0.72 e Å−3

Δρmin = −0.73 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) general, I. DOI: 10.1107/S1600536813033096/hb7170sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813033096/hb7170Isup2.hkl

Additional supporting information: crystallographic information; 3D view; checkCIF report

C31H28Cl3N3O2	Z = 2
Mr = 580.91	F(000) = 604
Triclinic, P1	Dx = 1.336 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.1901 (2) Å	Cell parameters from 7513 reflections
b = 11.6434 (3) Å	θ = 2.9–27.9°
c = 12.4270 (3) Å	µ = 0.35 mm−1
α = 99.477 (2)°	T = 293 K
β = 90.235 (2)°	Block, pale-yellow
γ = 114.893 (1)°	1.02 × 0.53 × 0.37 mm
V = 1443.77 (6) Å3

Nonius 590 KappaCCD diffractometer	6482 independent reflections
Radiation source: fine-focus sealed tube	4260 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
φ and ω scans	θmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→14
Tmin = 0.880, Tmax = 0.994	k = −15→14
11344 measured reflections	l = −16→15

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0632P)2 + 0.8473P] where P = (Fo2 + 2Fc2)/3
6482 reflections	(Δ/σ)max < 0.001
354 parameters	Δρmax = 0.72 e Å−3
0 restraints	Δρmin = −0.73 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.75652 (9)	0.88544 (7)	0.62569 (9)	0.0843 (3)
Cl2	0.18456 (16)	0.46678 (12)	0.97683 (11)	0.1288 (5)
Cl3	0.08381 (9)	−0.48680 (8)	0.27827 (7)	0.0746 (3)
O1	0.13605 (17)	0.13409 (17)	0.65765 (16)	0.0535 (5)
O2	0.37169 (18)	−0.08975 (17)	0.88375 (15)	0.0527 (5)
N1	0.48196 (18)	0.11736 (18)	0.73216 (16)	0.0388 (4)
N2	0.11620 (19)	−0.05244 (19)	0.87264 (16)	0.0433 (5)
N3	0.4280 (2)	0.1109 (2)	0.98503 (17)	0.0524 (5)
H3n	0.4902	0.1139	1.0278	0.063*
C1	0.2438 (2)	0.0150 (2)	0.72095 (18)	0.0352 (5)
C2	0.3678 (2)	0.0046 (2)	0.67812 (19)	0.0388 (5)
H2A	0.3713	−0.0728	0.6938	0.047*
H2B	0.3663	0.0006	0.5995	0.047*
C3	0.4971 (2)	0.2310 (2)	0.6878 (2)	0.0427 (5)
H3A	0.5315	0.2262	0.6165	0.051*
H3B	0.5614	0.3072	0.7354	0.051*
C4	0.3699 (2)	0.2447 (2)	0.67642 (18)	0.0381 (5)
C5	0.2403 (2)	0.1327 (2)	0.68197 (18)	0.0375 (5)
C6	0.2491 (2)	0.0382 (2)	0.85091 (18)	0.0370 (5)
C7	0.0761 (3)	−0.1661 (2)	0.7874 (2)	0.0485 (6)
H7A	−0.0180	−0.2201	0.7849	0.058*
H7B	0.1242	−0.2164	0.7981	0.058*
C8	0.1119 (2)	−0.1086 (2)	0.68402 (19)	0.0407 (5)
H8	0.0449	−0.0790	0.6682	0.049*
C9	0.6045 (3)	0.0993 (3)	0.7295 (3)	0.0542 (7)
H9A	0.6395	0.1114	0.6589	0.065*
H9B	0.5841	0.0116	0.7373	0.065*
C10	0.7081 (3)	0.1904 (3)	0.8178 (3)	0.0718 (9)
H10A	0.7305	0.2774	0.8095	0.108*
H10B	0.7854	0.1743	0.8125	0.108*
H10C	0.6747	0.1778	0.8880	0.108*
C11	0.1021 (3)	−0.0799 (3)	0.9836 (2)	0.0609 (7)
H11A	0.0106	−0.1300	0.9925	0.091*
H11B	0.1349	−0.0004	1.0355	0.091*
H11C	0.1517	−0.1274	0.9959	0.091*
C12	0.3628 (3)	0.3537 (2)	0.66025 (19)	0.0424 (5)
H12	0.2769	0.3464	0.6538	0.051*
C13	0.4638 (2)	0.4803 (2)	0.65098 (18)	0.0405 (5)
C14	0.4248 (3)	0.5800 (3)	0.6556 (2)	0.0534 (7)
H14	0.3366	0.5627	0.6642	0.064*
C15	0.5127 (3)	0.7033 (3)	0.6478 (3)	0.0611 (8)
H15	0.4839	0.7679	0.6510	0.073*
C16	0.6433 (3)	0.7303 (2)	0.6353 (2)	0.0537 (7)
C17	0.6857 (3)	0.6346 (3)	0.6289 (2)	0.0538 (7)
H17	0.7740	0.6528	0.6198	0.065*
C18	0.5963 (3)	0.5111 (2)	0.6361 (2)	0.0497 (6)
H18	0.6255	0.4466	0.6309	0.060*
C19	0.3588 (2)	0.0111 (2)	0.9046 (2)	0.0441 (6)
C20	0.3866 (3)	0.2094 (3)	0.9908 (2)	0.0519 (6)
C21	0.4321 (4)	0.3248 (3)	1.0627 (3)	0.0784 (10)
H21	0.5032	0.3489	1.1138	0.094*
C22	0.3694 (5)	0.4044 (3)	1.0570 (3)	0.0883 (12)
H22	0.3992	0.4836	1.1040	0.106*
C23	0.2635 (4)	0.3662 (3)	0.9821 (3)	0.0741 (10)
C24	0.2167 (3)	0.2502 (3)	0.9093 (2)	0.0527 (7)
H24	0.1443	0.2256	0.8594	0.063*
C25	0.2810 (2)	0.1722 (2)	0.91300 (19)	0.0427 (6)
C26	0.1113 (2)	−0.2007 (2)	0.5831 (2)	0.0407 (5)
C27	0.1627 (3)	−0.2913 (2)	0.5846 (2)	0.0485 (6)
H27	0.2025	−0.2933	0.6496	0.058*
C28	0.1555 (3)	−0.3778 (2)	0.4911 (2)	0.0518 (6)
H28	0.1906	−0.4371	0.4932	0.062*
C29	0.0960 (3)	−0.3750 (2)	0.3951 (2)	0.0501 (6)
C30	0.0446 (3)	−0.2871 (3)	0.3903 (2)	0.0530 (6)
H30	0.0049	−0.2858	0.3249	0.064*
C31	0.0529 (3)	−0.2008 (2)	0.4842 (2)	0.0479 (6)
H31	0.0184	−0.1412	0.4810	0.057*

	U11	U22	U33	U12	U13	U23
Cl1	0.0726 (5)	0.0396 (4)	0.1372 (8)	0.0211 (4)	0.0221 (5)	0.0141 (4)
Cl2	0.1991 (14)	0.0931 (8)	0.1389 (10)	0.1089 (9)	0.0425 (9)	0.0100 (7)
Cl3	0.0954 (6)	0.0525 (4)	0.0640 (5)	0.0258 (4)	0.0110 (4)	−0.0047 (3)
O1	0.0433 (10)	0.0552 (11)	0.0732 (12)	0.0273 (9)	−0.0027 (9)	0.0251 (9)
O2	0.0540 (11)	0.0530 (11)	0.0630 (11)	0.0307 (9)	−0.0014 (9)	0.0207 (9)
N1	0.0349 (10)	0.0363 (10)	0.0505 (11)	0.0202 (9)	0.0005 (8)	0.0086 (9)
N2	0.0421 (11)	0.0459 (12)	0.0451 (11)	0.0204 (10)	0.0071 (9)	0.0121 (9)
N3	0.0534 (13)	0.0570 (14)	0.0457 (12)	0.0222 (11)	−0.0104 (10)	0.0108 (11)
C1	0.0361 (12)	0.0351 (11)	0.0389 (12)	0.0194 (10)	0.0001 (9)	0.0066 (9)
C2	0.0422 (13)	0.0370 (12)	0.0413 (13)	0.0218 (11)	0.0008 (10)	0.0048 (10)
C3	0.0439 (13)	0.0359 (12)	0.0521 (14)	0.0196 (11)	0.0036 (11)	0.0113 (11)
C4	0.0454 (13)	0.0388 (12)	0.0351 (12)	0.0223 (11)	0.0018 (10)	0.0087 (10)
C5	0.0426 (13)	0.0408 (12)	0.0340 (11)	0.0224 (11)	−0.0001 (9)	0.0074 (10)
C6	0.0375 (12)	0.0370 (12)	0.0397 (12)	0.0182 (10)	0.0004 (9)	0.0091 (10)
C7	0.0411 (14)	0.0407 (13)	0.0587 (16)	0.0120 (11)	0.0032 (11)	0.0114 (12)
C8	0.0367 (12)	0.0389 (12)	0.0485 (14)	0.0185 (10)	−0.0033 (10)	0.0064 (10)
C9	0.0404 (14)	0.0482 (15)	0.0819 (19)	0.0249 (12)	0.0036 (13)	0.0162 (14)
C10	0.0414 (16)	0.083 (2)	0.094 (2)	0.0232 (16)	0.0001 (15)	0.0325 (19)
C11	0.0635 (18)	0.0696 (19)	0.0572 (17)	0.0301 (16)	0.0193 (14)	0.0268 (15)
C12	0.0490 (14)	0.0449 (13)	0.0405 (13)	0.0261 (12)	0.0026 (10)	0.0102 (11)
C13	0.0508 (14)	0.0392 (12)	0.0368 (12)	0.0242 (11)	−0.0013 (10)	0.0072 (10)
C14	0.0502 (15)	0.0458 (15)	0.0723 (18)	0.0274 (13)	0.0013 (13)	0.0133 (13)
C15	0.0601 (18)	0.0401 (15)	0.089 (2)	0.0278 (14)	0.0019 (15)	0.0099 (14)
C16	0.0580 (17)	0.0357 (13)	0.0656 (17)	0.0194 (12)	0.0047 (13)	0.0063 (12)
C17	0.0545 (16)	0.0475 (15)	0.0666 (17)	0.0278 (13)	0.0118 (13)	0.0129 (13)
C18	0.0603 (16)	0.0436 (14)	0.0569 (16)	0.0315 (13)	0.0118 (13)	0.0141 (12)
C19	0.0434 (14)	0.0485 (14)	0.0446 (14)	0.0207 (12)	0.0012 (11)	0.0164 (12)
C20	0.0623 (17)	0.0486 (15)	0.0371 (13)	0.0167 (13)	0.0002 (12)	0.0064 (11)
C21	0.105 (3)	0.062 (2)	0.0463 (17)	0.020 (2)	−0.0093 (17)	−0.0034 (15)
C22	0.141 (4)	0.054 (2)	0.057 (2)	0.036 (2)	0.013 (2)	−0.0079 (16)
C23	0.118 (3)	0.0525 (18)	0.063 (2)	0.047 (2)	0.028 (2)	0.0078 (15)
C24	0.0703 (18)	0.0499 (15)	0.0479 (15)	0.0344 (14)	0.0157 (13)	0.0105 (12)
C25	0.0527 (15)	0.0417 (13)	0.0361 (12)	0.0216 (12)	0.0068 (10)	0.0086 (10)
C26	0.0357 (12)	0.0341 (12)	0.0507 (14)	0.0142 (10)	−0.0038 (10)	0.0058 (10)
C27	0.0516 (15)	0.0440 (14)	0.0542 (15)	0.0248 (12)	−0.0038 (12)	0.0089 (12)
C28	0.0580 (16)	0.0399 (14)	0.0613 (17)	0.0250 (13)	0.0053 (13)	0.0077 (12)
C29	0.0508 (15)	0.0379 (13)	0.0527 (15)	0.0122 (12)	0.0064 (12)	0.0033 (11)
C30	0.0546 (16)	0.0544 (16)	0.0486 (15)	0.0230 (13)	−0.0057 (12)	0.0068 (12)
C31	0.0478 (14)	0.0469 (14)	0.0524 (15)	0.0241 (12)	−0.0056 (11)	0.0079 (12)

Cl1—C16	1.740 (3)	C10—H10B	0.9600
Cl2—C23	1.747 (3)	C10—H10C	0.9600
Cl3—C29	1.745 (3)	C11—H11A	0.9600
O1—C5	1.211 (3)	C11—H11B	0.9600
O2—C19	1.229 (3)	C11—H11C	0.9600
N1—C2	1.448 (3)	C12—C13	1.456 (3)
N1—C3	1.461 (3)	C12—H12	0.9300
N1—C9	1.472 (3)	C13—C18	1.392 (4)
N2—C7	1.453 (3)	C13—C14	1.395 (3)
N2—C11	1.461 (3)	C14—C15	1.377 (4)
N2—C6	1.475 (3)	C14—H14	0.9300
N3—C19	1.343 (3)	C15—C16	1.375 (4)
N3—C20	1.398 (3)	C15—H15	0.9300
N3—H3n	0.8600	C16—C17	1.375 (4)
C1—C2	1.532 (3)	C17—C18	1.382 (4)
C1—C5	1.543 (3)	C17—H17	0.9300
C1—C8	1.565 (3)	C18—H18	0.9300
C1—C6	1.589 (3)	C20—C21	1.373 (4)
C2—H2A	0.9700	C20—C25	1.393 (4)
C2—H2B	0.9700	C21—C22	1.387 (5)
C3—C4	1.506 (3)	C21—H21	0.9300
C3—H3A	0.9700	C22—C23	1.371 (5)
C3—H3B	0.9700	C22—H22	0.9300
C4—C12	1.351 (3)	C23—C24	1.384 (4)
C4—C5	1.499 (3)	C24—C25	1.381 (3)
C6—C25	1.514 (3)	C24—H24	0.9300
C6—C19	1.561 (3)	C26—C31	1.389 (3)
C7—C8	1.524 (3)	C26—C27	1.401 (3)
C7—H7A	0.9700	C27—C28	1.384 (4)
C7—H7B	0.9700	C27—H27	0.9300
C8—C26	1.508 (3)	C28—C29	1.376 (4)
C8—H8	0.9800	C28—H28	0.9300
C9—C10	1.498 (4)	C29—C30	1.378 (4)
C9—H9A	0.9700	C30—C31	1.384 (4)
C9—H9B	0.9700	C30—H30	0.9300
C10—H10A	0.9600	C31—H31	0.9300
C2—N1—C3	110.85 (18)	H11A—C11—H11B	109.5
C2—N1—C9	113.09 (19)	N2—C11—H11C	109.5
C3—N1—C9	111.41 (19)	H11A—C11—H11C	109.5
C7—N2—C11	114.2 (2)	H11B—C11—H11C	109.5
C7—N2—C6	106.79 (18)	C4—C12—C13	132.3 (2)
C11—N2—C6	115.8 (2)	C4—C12—H12	113.9
C19—N3—C20	111.8 (2)	C13—C12—H12	113.9
C19—N3—H3n	124.1	C18—C13—C14	116.6 (2)
C20—N3—H3n	124.1	C18—C13—C12	125.9 (2)
C2—C1—C5	106.00 (18)	C14—C13—C12	117.5 (2)
C2—C1—C8	114.65 (18)	C15—C14—C13	122.0 (3)
C5—C1—C8	111.33 (17)	C15—C14—H14	119.0
C2—C1—C6	112.13 (17)	C13—C14—H14	119.0
C5—C1—C6	108.72 (17)	C16—C15—C14	119.6 (2)
C8—C1—C6	103.98 (17)	C16—C15—H15	120.2
N1—C2—C1	107.91 (18)	C14—C15—H15	120.2
N1—C2—H2A	110.1	C15—C16—C17	120.3 (3)
C1—C2—H2A	110.1	C15—C16—Cl1	120.5 (2)
N1—C2—H2B	110.1	C17—C16—Cl1	119.2 (2)
C1—C2—H2B	110.1	C16—C17—C18	119.5 (3)
H2A—C2—H2B	108.4	C16—C17—H17	120.3
N1—C3—C4	113.32 (19)	C18—C17—H17	120.3
N1—C3—H3A	108.9	C17—C18—C13	122.0 (2)
C4—C3—H3A	108.9	C17—C18—H18	119.0
N1—C3—H3B	108.9	C13—C18—H18	119.0
C4—C3—H3B	108.9	O2—C19—N3	125.4 (2)
H3A—C3—H3B	107.7	O2—C19—C6	125.6 (2)
C12—C4—C5	115.8 (2)	N3—C19—C6	108.6 (2)
C12—C4—C3	124.2 (2)	C21—C20—C25	121.6 (3)
C5—C4—C3	120.06 (19)	C21—C20—N3	128.8 (3)
O1—C5—C4	121.7 (2)	C25—C20—N3	109.6 (2)
O1—C5—C1	120.7 (2)	C20—C21—C22	118.4 (3)
C4—C5—C1	117.58 (18)	C20—C21—H21	120.8
N2—C6—C25	110.00 (19)	C22—C21—H21	120.8
N2—C6—C19	111.18 (18)	C23—C22—C21	119.9 (3)
C25—C6—C19	100.62 (19)	C23—C22—H22	120.0
N2—C6—C1	103.23 (17)	C21—C22—H22	120.0
C25—C6—C1	118.74 (17)	C22—C23—C24	122.3 (3)
C19—C6—C1	113.26 (18)	C22—C23—Cl2	119.4 (3)
N2—C7—C8	102.53 (19)	C24—C23—Cl2	118.3 (3)
N2—C7—H7A	111.3	C25—C24—C23	117.9 (3)
C8—C7—H7A	111.3	C25—C24—H24	121.1
N2—C7—H7B	111.3	C23—C24—H24	121.1
C8—C7—H7B	111.3	C24—C25—C20	119.9 (2)
H7A—C7—H7B	109.2	C24—C25—C6	130.6 (2)
C26—C8—C7	115.4 (2)	C20—C25—C6	109.2 (2)
C26—C8—C1	117.06 (19)	C31—C26—C27	117.5 (2)
C7—C8—C1	103.79 (18)	C31—C26—C8	119.5 (2)
C26—C8—H8	106.6	C27—C26—C8	122.9 (2)
C7—C8—H8	106.6	C28—C27—C26	121.3 (2)
C1—C8—H8	106.6	C28—C27—H27	119.4
N1—C9—C10	112.9 (2)	C26—C27—H27	119.4
N1—C9—H9A	109.0	C29—C28—C27	119.2 (2)
C10—C9—H9A	109.0	C29—C28—H28	120.4
N1—C9—H9B	109.0	C27—C28—H28	120.4
C10—C9—H9B	109.0	C28—C29—C30	121.1 (2)
H9A—C9—H9B	107.8	C28—C29—Cl3	119.0 (2)
C9—C10—H10A	109.5	C30—C29—Cl3	119.8 (2)
C9—C10—H10B	109.5	C29—C30—C31	119.1 (2)
H10A—C10—H10B	109.5	C29—C30—H30	120.5
C9—C10—H10C	109.5	C31—C30—H30	120.5
H10A—C10—H10C	109.5	C30—C31—C26	121.8 (2)
H10B—C10—H10C	109.5	C30—C31—H31	119.1
N2—C11—H11A	109.5	C26—C31—H31	119.1
N2—C11—H11B	109.5
C3—N1—C2—C1	−74.5 (2)	C13—C14—C15—C16	−0.1 (5)
C9—N1—C2—C1	159.54 (19)	C14—C15—C16—C17	1.0 (5)
C5—C1—C2—N1	65.3 (2)	C14—C15—C16—Cl1	−179.8 (2)
C8—C1—C2—N1	−171.45 (17)	C15—C16—C17—C18	−0.6 (4)
C6—C1—C2—N1	−53.2 (2)	Cl1—C16—C17—C18	−179.8 (2)
C2—N1—C3—C4	46.3 (3)	C16—C17—C18—C13	−0.7 (4)
C9—N1—C3—C4	173.2 (2)	C14—C13—C18—C17	1.5 (4)
N1—C3—C4—C12	165.1 (2)	C12—C13—C18—C17	−179.6 (2)
N1—C3—C4—C5	−15.4 (3)	C20—N3—C19—O2	−177.5 (2)
C12—C4—C5—O1	10.4 (3)	C20—N3—C19—C6	−3.7 (3)
C3—C4—C5—O1	−169.2 (2)	N2—C6—C19—O2	60.9 (3)
C12—C4—C5—C1	−169.1 (2)	C25—C6—C19—O2	177.3 (2)
C3—C4—C5—C1	11.3 (3)	C1—C6—C19—O2	−54.8 (3)
C2—C1—C5—O1	146.0 (2)	N2—C6—C19—N3	−112.9 (2)
C8—C1—C5—O1	20.7 (3)	C25—C6—C19—N3	3.6 (2)
C6—C1—C5—O1	−93.2 (3)	C1—C6—C19—N3	131.4 (2)
C2—C1—C5—C4	−34.5 (3)	C19—N3—C20—C21	179.0 (3)
C8—C1—C5—C4	−159.77 (19)	C19—N3—C20—C25	2.2 (3)
C6—C1—C5—C4	86.3 (2)	C25—C20—C21—C22	0.6 (5)
C7—N2—C6—C25	162.75 (18)	N3—C20—C21—C22	−175.8 (3)
C11—N2—C6—C25	−68.9 (3)	C20—C21—C22—C23	1.0 (5)
C7—N2—C6—C19	−86.7 (2)	C21—C22—C23—C24	−1.0 (5)
C11—N2—C6—C19	41.7 (3)	C21—C22—C23—Cl2	179.4 (3)
C7—N2—C6—C1	35.1 (2)	C22—C23—C24—C25	−0.5 (5)
C11—N2—C6—C1	163.4 (2)	Cl2—C23—C24—C25	179.1 (2)
C2—C1—C6—N2	−134.84 (18)	C23—C24—C25—C20	2.1 (4)
C5—C1—C6—N2	108.29 (19)	C23—C24—C25—C6	175.3 (3)
C8—C1—C6—N2	−10.4 (2)	C21—C20—C25—C24	−2.2 (4)
C2—C1—C6—C25	103.2 (2)	N3—C20—C25—C24	174.9 (2)
C5—C1—C6—C25	−13.7 (3)	C21—C20—C25—C6	−176.8 (3)
C8—C1—C6—C25	−132.4 (2)	N3—C20—C25—C6	0.3 (3)
C2—C1—C6—C19	−14.5 (3)	N2—C6—C25—C24	−58.7 (3)
C5—C1—C6—C19	−131.4 (2)	C19—C6—C25—C24	−176.1 (2)
C8—C1—C6—C19	109.9 (2)	C1—C6—C25—C24	59.8 (3)
C11—N2—C7—C8	−175.4 (2)	N2—C6—C25—C20	115.1 (2)
C6—N2—C7—C8	−46.1 (2)	C19—C6—C25—C20	−2.3 (2)
N2—C7—C8—C26	166.56 (19)	C1—C6—C25—C20	−126.4 (2)
N2—C7—C8—C1	37.1 (2)	C7—C8—C26—C31	135.5 (2)
C2—C1—C8—C26	−21.6 (3)	C1—C8—C26—C31	−101.9 (3)
C5—C1—C8—C26	98.7 (2)	C7—C8—C26—C27	−41.9 (3)
C6—C1—C8—C26	−144.36 (19)	C1—C8—C26—C27	80.7 (3)
C2—C1—C8—C7	106.9 (2)	C31—C26—C27—C28	−0.1 (4)
C5—C1—C8—C7	−132.80 (19)	C8—C26—C27—C28	177.3 (2)
C6—C1—C8—C7	−15.9 (2)	C26—C27—C28—C29	−0.4 (4)
C2—N1—C9—C10	−158.0 (2)	C27—C28—C29—C30	0.6 (4)
C3—N1—C9—C10	76.3 (3)	C27—C28—C29—Cl3	−178.5 (2)
C5—C4—C12—C13	179.6 (2)	C28—C29—C30—C31	−0.3 (4)
C3—C4—C12—C13	−0.9 (4)	Cl3—C29—C30—C31	178.8 (2)
C4—C12—C13—C18	13.4 (4)	C29—C30—C31—C26	−0.2 (4)
C4—C12—C13—C14	−167.7 (3)	C27—C26—C31—C30	0.4 (4)
C18—C13—C14—C15	−1.1 (4)	C8—C26—C31—C30	−177.2 (2)
C12—C13—C14—C15	179.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3n···O2i	0.86	2.03	2.883 (3)	170
C31—H31···O1ii	0.93	2.47	3.160 (4)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3n⋯O2i	0.86	2.03	2.883 (3)	170
C31—H31⋯O1ii	0.93	2.47	3.160 (4)	131

Symmetry codes: (i) ; (ii) .