5''-Benzyl-idene-5-chloro-1',1''-dimethyl-4'-phenyl-dispiro-[indoline-3,2'-pyrrolidine-3',3''-piperidine]-2,4''-dione.

The title compound, C30H28ClN3O2, features two spiro links, one connecting the piperidine and pyrrolidine rings, and the other connecting the pyrrolidine ring and indole residue. The configuration about the ethene bond is E. The piperidine ring adopts a half-chair conformation where the C atom connected to the spiro-C atom lies 0.713 (3) Å out of the plane of the remaining five atoms (r.m.s. deviation = 0.086 Å). The pyrrolidine ring has an envelope conformation with the flap atom being the methyl-ene C atom. Centrosymmetric eight-membered {⋯HNCO}2 amide synthons feature in the crystal packing. These are consolidated into a three-dimensional architecture by phen-yl-pyrrolidine C-H⋯N and chloro-benzene-pyrrolidine-bound phenyl C-H⋯π inter-actions.

Related literature

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

Experimental

Crystal data

C30H28ClN3O2

M = 498.00

Monoclinic,

a = 10.5028 (3) Å

b = 20.4117 (6) Å

c = 11.9951 (4) Å

β = 94.877 (1)°

V = 2562.20 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 293 K

0.52 × 0.22 × 0.15 mm

Data collection

Nonius 590 KappaCCD diffractometer

10395 measured reflections

5842 independent reflections

2547 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.137

S = 0.94

5842 reflections

327 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.35 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DEn class="Chemical">NZO 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/S1600536813032765/hg5367sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813032765/hg5367Isup2.hkl

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

C30H28ClN3O2	F(000) = 1048
Mr = 498.00	Dx = 1.291 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5029 reflections
a = 10.5028 (3) Å	θ = 2.9–27.5°
b = 20.4117 (6) Å	µ = 0.18 mm−1
c = 11.9951 (4) Å	T = 293 K
β = 94.877 (1)°	Block, colourless
V = 2562.20 (14) Å3	0.52 × 0.22 × 0.15 mm
Z = 4

Nonius 590 KappaCCD diffractometer	2547 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.066
Graphite monochromator	θmax = 27.5°, θmin = 3.2°
φ and ω scans	h = −13→13
10395 measured reflections	k = −24→26
5842 independent reflections	l = −15→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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H-atom parameters constrained
S = 0.94	w = 1/[σ2(Fo2) + (0.0569P)2] where P = (Fo2 + 2Fc2)/3
5842 reflections	(Δ/σ)max = 0.001
327 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.35 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	1.05716 (7)	0.16826 (4)	−0.06845 (7)	0.0777 (3)
O1	0.70008 (15)	0.22207 (8)	0.17686 (15)	0.0518 (5)
O2	0.83631 (15)	0.01572 (8)	0.45243 (14)	0.0501 (5)
N1	0.87248 (16)	0.16478 (9)	0.47693 (16)	0.0395 (5)
N2	0.73065 (16)	0.03868 (9)	0.21124 (16)	0.0425 (5)
N3	1.01454 (17)	0.04625 (9)	0.36752 (17)	0.0441 (5)
H3n	1.0711	0.0286	0.4142	0.053*
C1	0.72419 (19)	0.13839 (11)	0.31799 (19)	0.0354 (6)
C2	0.7398 (2)	0.14837 (11)	0.44474 (19)	0.0389 (6)
H2A	0.6845	0.1835	0.4659	0.047*
H2B	0.7165	0.1086	0.4825	0.047*
C3	0.8953 (2)	0.23259 (11)	0.4469 (2)	0.0425 (6)
H3A	0.9855	0.2423	0.4618	0.051*
H3B	0.8485	0.2612	0.4935	0.051*
C4	0.8552 (2)	0.24660 (11)	0.32605 (19)	0.0370 (6)
C5	0.7557 (2)	0.20414 (11)	0.2654 (2)	0.0377 (6)
C6	0.81725 (19)	0.08258 (11)	0.27869 (19)	0.0364 (6)
C7	0.6081 (2)	0.04033 (11)	0.2593 (2)	0.0463 (7)
H7A	0.6121	0.0177	0.3307	0.056*
H7B	0.5409	0.0212	0.2091	0.056*
C8	0.58871 (19)	0.11328 (11)	0.2732 (2)	0.0391 (6)
H8	0.5710	0.1315	0.1979	0.047*
C9	0.9106 (2)	0.15392 (13)	0.5956 (2)	0.0562 (7)
H9A	0.8554	0.1784	0.6401	0.084*
H9B	0.9972	0.1681	0.6124	0.084*
H9C	0.9041	0.1081	0.6124	0.084*
C10	0.7805 (2)	−0.02622 (13)	0.1881 (2)	0.0615 (8)
H10A	0.8615	−0.0219	0.1573	0.092*
H10B	0.7216	−0.0485	0.1354	0.092*
H10C	0.7911	−0.0510	0.2562	0.092*
C11	0.9050 (2)	0.29475 (11)	0.2683 (2)	0.0423 (6)
H11	0.8740	0.2975	0.1935	0.051*
C12	1.0017 (2)	0.34419 (11)	0.3053 (2)	0.0408 (6)
C13	1.0215 (2)	0.36746 (13)	0.4136 (2)	0.0546 (7)
H13	0.9709	0.3519	0.4678	0.066*
C14	1.1149 (3)	0.41337 (14)	0.4432 (3)	0.0657 (8)
H14	1.1273	0.4279	0.5168	0.079*
C15	1.1892 (3)	0.43743 (14)	0.3646 (3)	0.0658 (8)
H15	1.2537	0.4674	0.3849	0.079*
C16	1.1685 (3)	0.41725 (14)	0.2555 (3)	0.0667 (9)
H16	1.2169	0.4347	0.2012	0.080*
C17	1.0760 (2)	0.37125 (12)	0.2266 (2)	0.0540 (7)
H17	1.0627	0.3579	0.1524	0.065*
C18	0.8882 (2)	0.04577 (11)	0.3795 (2)	0.0407 (6)
C19	1.0428 (2)	0.07885 (11)	0.2700 (2)	0.0385 (6)
C20	1.1587 (2)	0.08588 (12)	0.2266 (2)	0.0485 (7)
H20	1.2336	0.0717	0.2662	0.058*
C21	1.1613 (2)	0.11466 (12)	0.1225 (2)	0.0524 (7)
H21	1.2388	0.1201	0.0915	0.063*
C22	1.0499 (2)	0.13532 (12)	0.0645 (2)	0.0478 (7)
C23	0.9324 (2)	0.12955 (11)	0.1090 (2)	0.0435 (6)
H23	0.8577	0.1440	0.0693	0.052*
C24	0.9298 (2)	0.10180 (11)	0.2136 (2)	0.0368 (6)
C25	0.4792 (2)	0.13400 (12)	0.3399 (2)	0.0394 (6)
C26	0.4383 (2)	0.09737 (14)	0.4274 (2)	0.0544 (7)
H26	0.4793	0.0582	0.4477	0.065*
C27	0.3363 (2)	0.11858 (17)	0.4853 (2)	0.0652 (8)
H27	0.3094	0.0935	0.5436	0.078*
C28	0.2756 (3)	0.17634 (18)	0.4566 (3)	0.0722 (9)
H28	0.2083	0.1907	0.4959	0.087*
C29	0.3145 (3)	0.21279 (15)	0.3698 (3)	0.0701 (9)
H29	0.2731	0.2518	0.3497	0.084*
C30	0.4153 (2)	0.19161 (13)	0.3119 (2)	0.0553 (7)
H30	0.4406	0.2167	0.2529	0.066*

	U11	U22	U33	U12	U13	U23
Cl1	0.0823 (5)	0.0892 (6)	0.0655 (6)	0.0142 (4)	0.0285 (4)	0.0289 (4)
O1	0.0515 (10)	0.0547 (11)	0.0467 (12)	−0.0077 (8)	−0.0102 (9)	0.0147 (9)
O2	0.0486 (10)	0.0543 (11)	0.0466 (12)	−0.0018 (9)	−0.0003 (9)	0.0159 (9)
N1	0.0364 (11)	0.0465 (13)	0.0341 (13)	−0.0047 (9)	−0.0047 (9)	0.0055 (10)
N2	0.0362 (11)	0.0430 (13)	0.0475 (14)	−0.0005 (10)	−0.0004 (10)	−0.0057 (10)
N3	0.0350 (11)	0.0538 (14)	0.0420 (14)	0.0067 (10)	−0.0051 (10)	0.0087 (10)
C1	0.0314 (12)	0.0416 (15)	0.0326 (15)	−0.0011 (11)	−0.0019 (10)	0.0045 (12)
C2	0.0385 (13)	0.0408 (15)	0.0369 (16)	−0.0052 (11)	0.0010 (11)	0.0029 (12)
C3	0.0380 (13)	0.0440 (16)	0.0445 (17)	−0.0070 (11)	−0.0019 (11)	0.0012 (13)
C4	0.0345 (13)	0.0433 (15)	0.0328 (15)	−0.0015 (11)	0.0004 (11)	0.0029 (12)
C5	0.0338 (13)	0.0426 (15)	0.0365 (17)	0.0044 (11)	0.0027 (12)	0.0039 (13)
C6	0.0344 (12)	0.0389 (14)	0.0349 (15)	−0.0007 (11)	−0.0032 (11)	0.0030 (11)
C7	0.0381 (14)	0.0516 (17)	0.0479 (17)	−0.0072 (12)	−0.0034 (12)	−0.0004 (13)
C8	0.0333 (12)	0.0450 (16)	0.0378 (15)	−0.0002 (11)	−0.0033 (11)	0.0037 (12)
C9	0.0597 (16)	0.0632 (19)	0.0434 (19)	−0.0088 (14)	−0.0096 (13)	0.0069 (14)
C10	0.0593 (17)	0.0547 (19)	0.070 (2)	−0.0006 (14)	0.0051 (15)	−0.0124 (15)
C11	0.0415 (14)	0.0472 (16)	0.0379 (16)	0.0002 (13)	0.0014 (12)	−0.0011 (13)
C12	0.0403 (13)	0.0411 (15)	0.0405 (17)	−0.0034 (12)	0.0010 (12)	0.0031 (13)
C13	0.0698 (18)	0.0511 (17)	0.0429 (19)	−0.0159 (15)	0.0052 (14)	0.0042 (14)
C14	0.085 (2)	0.060 (2)	0.049 (2)	−0.0203 (17)	−0.0112 (16)	0.0024 (16)
C15	0.0552 (18)	0.060 (2)	0.080 (3)	−0.0204 (14)	−0.0069 (17)	0.0028 (18)
C16	0.0612 (18)	0.066 (2)	0.076 (3)	−0.0189 (16)	0.0223 (17)	−0.0040 (18)
C17	0.0590 (16)	0.0555 (17)	0.0490 (19)	−0.0108 (15)	0.0136 (14)	−0.0047 (15)
C18	0.0404 (15)	0.0385 (15)	0.0424 (17)	0.0005 (12)	−0.0014 (12)	0.0041 (13)
C19	0.0393 (14)	0.0391 (15)	0.0363 (16)	0.0001 (11)	−0.0004 (12)	−0.0020 (12)
C20	0.0363 (14)	0.0548 (17)	0.0537 (19)	0.0049 (12)	0.0003 (13)	−0.0009 (14)
C21	0.0422 (15)	0.0568 (18)	0.060 (2)	−0.0043 (13)	0.0140 (14)	−0.0018 (15)
C22	0.0522 (16)	0.0494 (17)	0.0430 (18)	0.0022 (13)	0.0120 (14)	0.0046 (13)
C23	0.0407 (14)	0.0439 (16)	0.0450 (17)	0.0038 (12)	−0.0009 (12)	0.0048 (13)
C24	0.0375 (13)	0.0371 (14)	0.0354 (16)	0.0005 (11)	0.0001 (11)	−0.0005 (12)
C25	0.0291 (12)	0.0450 (16)	0.0430 (17)	−0.0059 (12)	−0.0040 (11)	−0.0003 (13)
C26	0.0436 (15)	0.0665 (19)	0.0527 (19)	−0.0041 (14)	0.0013 (14)	0.0088 (15)
C27	0.0514 (17)	0.095 (3)	0.050 (2)	−0.0111 (17)	0.0109 (15)	−0.0051 (17)
C28	0.0448 (17)	0.096 (3)	0.077 (3)	−0.0018 (18)	0.0135 (16)	−0.030 (2)
C29	0.0516 (18)	0.063 (2)	0.097 (3)	0.0026 (15)	0.0102 (18)	−0.0110 (19)
C30	0.0409 (15)	0.0537 (18)	0.071 (2)	−0.0044 (14)	0.0042 (14)	−0.0004 (15)

Cl1—C22	1.738 (3)	C10—H10C	0.9600
O1—C5	1.224 (3)	C11—C12	1.473 (3)
O2—C18	1.232 (3)	C11—H11	0.9300
N1—C2	1.453 (3)	C12—C13	1.382 (3)
N1—C3	1.455 (3)	C12—C17	1.390 (3)
N1—C9	1.463 (3)	C13—C14	1.381 (4)
N2—C7	1.454 (3)	C13—H13	0.9300
N2—C10	1.460 (3)	C14—C15	1.366 (4)
N2—C6	1.470 (3)	C14—H14	0.9300
N3—C18	1.347 (3)	C15—C16	1.371 (4)
N3—C19	1.400 (3)	C15—H15	0.9300
N3—H3n	0.8600	C16—C17	1.374 (3)
C1—C5	1.531 (3)	C16—H16	0.9300
C1—C2	1.529 (3)	C17—H17	0.9300
C1—C8	1.564 (3)	C19—C20	1.371 (3)
C1—C6	1.598 (3)	C19—C24	1.396 (3)
C2—H2A	0.9700	C20—C21	1.382 (3)
C2—H2B	0.9700	C20—H20	0.9300
C3—C4	1.502 (3)	C21—C22	1.375 (3)
C3—H3A	0.9700	C21—H21	0.9300
C3—H3B	0.9700	C22—C23	1.391 (3)
C4—C11	1.334 (3)	C23—C24	1.380 (3)
C4—C5	1.498 (3)	C23—H23	0.9300
C6—C24	1.522 (3)	C25—C30	1.381 (3)
C6—C18	1.559 (3)	C25—C26	1.386 (3)
C7—C8	1.514 (3)	C26—C27	1.394 (3)
C7—H7A	0.9700	C26—H26	0.9300
C7—H7B	0.9700	C27—C28	1.370 (4)
C8—C25	1.516 (3)	C27—H27	0.9300
C8—H8	0.9800	C28—C29	1.370 (4)
C9—H9A	0.9600	C28—H28	0.9300
C9—H9B	0.9600	C29—C30	1.384 (4)
C9—H9C	0.9600	C29—H29	0.9300
C10—H10A	0.9600	C30—H30	0.9300
C10—H10B	0.9600
C2—N1—C3	109.14 (18)	H10B—C10—H10C	109.5
C2—N1—C9	113.61 (17)	C4—C11—C12	129.7 (2)
C3—N1—C9	110.35 (18)	C4—C11—H11	115.2
C7—N2—C10	116.12 (18)	C12—C11—H11	115.2
C7—N2—C6	107.14 (17)	C13—C12—C17	117.0 (2)
C10—N2—C6	116.30 (18)	C13—C12—C11	124.3 (2)
C18—N3—C19	111.96 (19)	C17—C12—C11	118.7 (2)
C18—N3—H3n	124.0	C14—C13—C12	121.5 (2)
C19—N3—H3n	124.0	C14—C13—H13	119.3
C5—C1—C2	106.50 (19)	C12—C13—H13	119.3
C5—C1—C8	111.60 (18)	C15—C14—C13	120.1 (3)
C2—C1—C8	113.73 (17)	C15—C14—H14	120.0
C5—C1—C6	110.15 (16)	C13—C14—H14	120.0
C2—C1—C6	111.83 (18)	C14—C15—C16	119.8 (3)
C8—C1—C6	103.10 (17)	C14—C15—H15	120.1
N1—C2—C1	108.31 (17)	C16—C15—H15	120.1
N1—C2—H2A	110.0	C15—C16—C17	119.9 (3)
C1—C2—H2A	110.0	C15—C16—H16	120.1
N1—C2—H2B	110.0	C17—C16—H16	120.1
C1—C2—H2B	110.0	C16—C17—C12	121.7 (3)
H2A—C2—H2B	108.4	C16—C17—H17	119.2
N1—C3—C4	112.41 (19)	C12—C17—H17	119.2
N1—C3—H3A	109.1	O2—C18—N3	125.4 (2)
C4—C3—H3A	109.1	O2—C18—C6	125.4 (2)
N1—C3—H3B	109.1	N3—C18—C6	108.9 (2)
C4—C3—H3B	109.1	C20—C19—C24	121.8 (2)
H3A—C3—H3B	107.9	C20—C19—N3	128.7 (2)
C11—C4—C5	117.5 (2)	C24—C19—N3	109.40 (19)
C11—C4—C3	123.4 (2)	C19—C20—C21	118.2 (2)
C5—C4—C3	119.0 (2)	C19—C20—H20	120.9
O1—C5—C4	120.7 (2)	C21—C20—H20	120.9
O1—C5—C1	121.0 (2)	C22—C21—C20	120.4 (2)
C4—C5—C1	118.3 (2)	C22—C21—H21	119.8
N2—C6—C24	110.25 (18)	C20—C21—H21	119.8
N2—C6—C18	111.47 (18)	C21—C22—C23	121.6 (2)
C24—C6—C18	100.44 (17)	C21—C22—Cl1	118.77 (19)
N2—C6—C1	103.40 (16)	C23—C22—Cl1	119.6 (2)
C24—C6—C1	119.26 (18)	C24—C23—C22	118.1 (2)
C18—C6—C1	112.25 (18)	C24—C23—H23	121.0
N2—C7—C8	101.46 (17)	C22—C23—H23	121.0
N2—C7—H7A	111.5	C23—C24—C19	119.8 (2)
C8—C7—H7A	111.5	C23—C24—C6	130.4 (2)
N2—C7—H7B	111.5	C19—C24—C6	109.3 (2)
C8—C7—H7B	111.5	C30—C25—C26	117.9 (2)
H7A—C7—H7B	109.3	C30—C25—C8	118.9 (2)
C7—C8—C25	116.62 (19)	C26—C25—C8	123.2 (2)
C7—C8—C1	103.47 (17)	C25—C26—C27	120.7 (3)
C25—C8—C1	115.89 (19)	C25—C26—H26	119.7
C7—C8—H8	106.7	C27—C26—H26	119.7
C25—C8—H8	106.7	C28—C27—C26	120.2 (3)
C1—C8—H8	106.7	C28—C27—H27	119.9
N1—C9—H9A	109.5	C26—C27—H27	119.9
N1—C9—H9B	109.5	C29—C28—C27	119.7 (3)
H9A—C9—H9B	109.5	C29—C28—H28	120.1
N1—C9—H9C	109.5	C27—C28—H28	120.1
H9A—C9—H9C	109.5	C28—C29—C30	120.1 (3)
H9B—C9—H9C	109.5	C28—C29—H29	119.9
N2—C10—H10A	109.5	C30—C29—H29	119.9
N2—C10—H10B	109.5	C25—C30—C29	121.4 (3)
H10A—C10—H10B	109.5	C25—C30—H30	119.3
N2—C10—H10C	109.5	C29—C30—H30	119.3
H10A—C10—H10C	109.5
C3—N1—C2—C1	76.1 (2)	C11—C12—C13—C14	179.2 (2)
C9—N1—C2—C1	−160.35 (19)	C12—C13—C14—C15	0.8 (4)
C5—C1—C2—N1	−62.7 (2)	C13—C14—C15—C16	1.8 (4)
C8—C1—C2—N1	173.98 (18)	C14—C15—C16—C17	−2.2 (4)
C6—C1—C2—N1	57.7 (2)	C15—C16—C17—C12	0.0 (4)
C2—N1—C3—C4	−53.4 (2)	C13—C12—C17—C16	2.4 (4)
C9—N1—C3—C4	−178.89 (18)	C11—C12—C17—C16	−179.5 (2)
N1—C3—C4—C11	−155.0 (2)	C19—N3—C18—O2	173.4 (2)
N1—C3—C4—C5	24.1 (3)	C19—N3—C18—C6	−0.1 (3)
C11—C4—C5—O1	−17.4 (3)	N2—C6—C18—O2	−56.8 (3)
C3—C4—C5—O1	163.4 (2)	C24—C6—C18—O2	−173.6 (2)
C11—C4—C5—C1	163.4 (2)	C1—C6—C18—O2	58.7 (3)
C3—C4—C5—C1	−15.7 (3)	N2—C6—C18—N3	116.7 (2)
C2—C1—C5—O1	−145.8 (2)	C24—C6—C18—N3	0.0 (2)
C8—C1—C5—O1	−21.2 (3)	C1—C6—C18—N3	−127.80 (19)
C6—C1—C5—O1	92.7 (2)	C18—N3—C19—C20	−175.8 (2)
C2—C1—C5—C4	33.3 (2)	C18—N3—C19—C24	0.3 (3)
C8—C1—C5—C4	157.97 (19)	C24—C19—C20—C21	−2.2 (4)
C6—C1—C5—C4	−88.1 (2)	N3—C19—C20—C21	173.5 (2)
C7—N2—C6—C24	−160.87 (19)	C19—C20—C21—C22	−0.2 (4)
C10—N2—C6—C24	67.3 (3)	C20—C21—C22—C23	1.6 (4)
C7—N2—C6—C18	88.5 (2)	C20—C21—C22—Cl1	−177.5 (2)
C10—N2—C6—C18	−43.3 (3)	C21—C22—C23—C24	−0.5 (4)
C7—N2—C6—C1	−32.3 (2)	Cl1—C22—C23—C24	178.52 (19)
C10—N2—C6—C1	−164.09 (19)	C22—C23—C24—C19	−1.8 (3)
C5—C1—C6—N2	−114.14 (19)	C22—C23—C24—C6	−173.0 (2)
C2—C1—C6—N2	127.64 (18)	C20—C19—C24—C23	3.2 (3)
C8—C1—C6—N2	5.1 (2)	N3—C19—C24—C23	−173.2 (2)
C5—C1—C6—C24	8.6 (3)	C20—C19—C24—C6	176.1 (2)
C2—C1—C6—C24	−109.6 (2)	N3—C19—C24—C6	−0.3 (3)
C8—C1—C6—C24	127.8 (2)	N2—C6—C24—C23	54.4 (3)
C5—C1—C6—C18	125.6 (2)	C18—C6—C24—C23	172.1 (2)
C2—C1—C6—C18	7.4 (2)	C1—C6—C24—C23	−64.9 (3)
C8—C1—C6—C18	−115.19 (19)	N2—C6—C24—C19	−117.5 (2)
C10—N2—C7—C8	179.1 (2)	C18—C6—C24—C19	0.2 (2)
C6—N2—C7—C8	47.2 (2)	C1—C6—C24—C19	123.2 (2)
N2—C7—C8—C25	−170.10 (19)	C7—C8—C25—C30	−147.6 (2)
N2—C7—C8—C1	−41.6 (2)	C1—C8—C25—C30	90.2 (3)
C5—C1—C8—C7	140.24 (19)	C7—C8—C25—C26	31.5 (3)
C2—C1—C8—C7	−99.2 (2)	C1—C8—C25—C26	−90.7 (3)
C6—C1—C8—C7	22.0 (2)	C30—C25—C26—C27	−0.4 (4)
C5—C1—C8—C25	−90.8 (2)	C8—C25—C26—C27	−179.5 (2)
C2—C1—C8—C25	29.7 (3)	C25—C26—C27—C28	−0.4 (4)
C6—C1—C8—C25	150.97 (19)	C26—C27—C28—C29	0.8 (4)
C5—C4—C11—C12	179.0 (2)	C27—C28—C29—C30	−0.5 (4)
C3—C4—C11—C12	−1.9 (4)	C26—C25—C30—C29	0.7 (4)
C4—C11—C12—C13	−28.2 (4)	C8—C25—C30—C29	179.9 (2)
C4—C11—C12—C17	153.9 (2)	C28—C29—C30—C25	−0.3 (4)
C17—C12—C13—C14	−2.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3n···O2i	0.86	2.01	2.854 (3)	165
C14—H14···N2ii	0.93	2.58	3.480 (4)	163
C20—H20···Cg1iii	0.93	2.70	3.268 (3)	121

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C25–C30 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3n⋯O2i	0.86	2.01	2.854 (3)	165
C14—H14⋯N2ii	0.93	2.58	3.480 (4)	163
C20—H20⋯Cg1iii	0.93	2.70	3.268 (3)	121

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