5''-(4-Chloro-benzyl-idene)-4'-(4-chloro-phen-yl)-5-fluoro-1',1''-dimethyl-indoline-3-spiro-2'-pyrrolidine-3'-spiro-3''-piperidine-2,4''-dione.

The piperidine ring of the title compound, C(30)H(26)Cl(2)FN(3)O(2), adopts a twisted chair conformation. The pyrrolidine ring has a twisted envelope structure with the N atom at the flap [displaced by 0.592 (3) Å]. The fluoro-oxindole, chloro-phenyl and chloro-benzyl-idene groups are planar with r.m.s. deviations of 0.0348, 0.0048 and 0.0048 Å, respectively. The structure is stabilized by inter-molecular N-H⋯O hydrogen bonds.

Related literature

For biological applications of 1,4-dihydro­pyridine derivatives, see: Jerom & Spencer (1988 ▶); Perumal et al. (2001 ▶); Hagenbach & Gysin (1952 ▶); Mobio et al. (1989 ▶); Katritzky & Fan (1990 ▶); Ganellin & Spickett (1965 ▶); El-Subbagh et al. (2000 ▶). For their use as synthetic inter­mediates in the preparation of various pharmaceuticals, see: Wang & Wuorola (1992 ▶). For their ocurrence in natural products such as n class="Chemical">alkaloids, see: Angle & Breitenbucher (1995 ▶).

Experimental

Crystal data

C30H26Cl2FN3O2

M = 550.44

Monoclinic,

a = 16.694 (3) Å

b = 8.705 (4) Å

c = 18.474 (3) Å

β = 103.27 (4)°

V = 2613.3 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 293 K

0.23 × 0.21 × 0.18 mm

Data collection

Nonius MACH3 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.936, T max = 0.950

5427 measured reflections

4581 independent reflections

2891 reflections with I > 2σ(I)

R int = 0.020

3 standard reflections every 60 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.104

S = 1.02

4581 reflections

349 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811007550/zj2003sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007550/zj2003Isup2.hkl

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

C30H26Cl2FN3O2	F(000) = 1144
Mr = 550.44	Dx = 1.399 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 16.694 (3) Å	θ = 2–25°
b = 8.705 (4) Å	µ = 0.29 mm−1
c = 18.474 (3) Å	T = 293 K
β = 103.27 (4)°	Block, colourless
V = 2613.3 (14) Å3	0.23 × 0.21 × 0.18 mm
Z = 4

Nonius MACH3 diffractometer	2891 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
graphite	θmax = 25.0°, θmin = 2.3°
ω–2θ scans	h = 0→19
Absorption correction: ψ scan (North et al., 1968)	k = −1→10
Tmin = 0.936, Tmax = 0.950	l = −21→21
5427 measured reflections	3 standard reflections every 60 min
4581 independent reflections	intensity decay: none

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0445P)2 + 0.726P] where P = (Fo2 + 2Fc2)/3
4581 reflections	(Δ/σ)max = 0.001
349 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.33 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	0.15668 (5)	0.37573 (8)	0.72167 (3)	0.0831 (2)
Cl2	−0.36431 (5)	0.61752 (10)	0.00265 (4)	0.0919 (3)
N1	−0.05322 (10)	0.13961 (19)	0.27962 (9)	0.0464 (4)
O1	0.07132 (10)	0.52336 (18)	0.24553 (8)	0.0613 (4)
C8	0.03804 (12)	0.3538 (2)	0.33420 (11)	0.0419 (5)
F1	0.32228 (9)	0.21475 (19)	0.36806 (8)	0.0808 (5)
N3	0.05530 (14)	−0.1040 (2)	0.21711 (12)	0.0603 (6)
C12	−0.02137 (13)	0.2314 (2)	0.34544 (11)	0.0473 (5)
H12A	0.0060	0.1641	0.3854	0.057*
H12B	−0.0671	0.2797	0.3608	0.057*
C9	0.03991 (12)	0.4022 (2)	0.25700 (11)	0.0435 (5)
O2	−0.05184 (11)	−0.0289 (2)	0.12232 (10)	0.0724 (5)
N2	0.08528 (11)	0.2056 (2)	0.11641 (9)	0.0524 (5)
C20	0.12500 (14)	−0.0377 (3)	0.26298 (13)	0.0511 (6)
C15	0.12839 (13)	0.1176 (2)	0.24568 (11)	0.0448 (5)
C5	0.04926 (13)	0.3405 (3)	0.50697 (12)	0.0521 (6)
H5	0.0001	0.3012	0.4789	0.063*
C10	−0.00213 (12)	0.2963 (2)	0.19252 (11)	0.0420 (5)
C11	−0.07990 (13)	0.2364 (2)	0.21440 (11)	0.0459 (5)
H11A	−0.1125	0.3216	0.2256	0.055*
H11B	−0.1132	0.1776	0.1739	0.055*
C4	0.10401 (13)	0.4086 (2)	0.47049 (11)	0.0451 (5)
C17	0.25566 (14)	0.1306 (3)	0.33291 (13)	0.0570 (6)
C25	−0.10489 (14)	0.4406 (2)	0.08703 (11)	0.0475 (5)
C28	−0.26410 (16)	0.5504 (3)	0.03646 (13)	0.0592 (6)
C24	−0.01808 (13)	0.3837 (3)	0.11635 (11)	0.0487 (5)
H24	0.0175	0.4746	0.1241	0.058*
C14	0.05642 (13)	0.1582 (2)	0.18243 (11)	0.0464 (5)
C16	0.19562 (13)	0.2034 (3)	0.28079 (12)	0.0503 (5)
H16	0.2002	0.3068	0.2696	0.060*
C26	−0.12471 (17)	0.5925 (3)	0.09730 (13)	0.0588 (6)
H26	−0.0836	0.6590	0.1214	0.071*
C1	0.13761 (16)	0.3869 (3)	0.62522 (12)	0.0577 (6)
C3	0.17622 (15)	0.4682 (3)	0.51528 (13)	0.0566 (6)
H3	0.2138	0.5169	0.4929	0.068*
C7	0.09049 (13)	0.4260 (3)	0.38996 (12)	0.0468 (5)
H7	0.1237	0.4993	0.3747	0.056*
C21	0.01022 (16)	−0.0003 (3)	0.16971 (14)	0.0549 (6)
C18	0.25207 (16)	−0.0208 (3)	0.35107 (13)	0.0630 (7)
H18	0.2942	−0.0649	0.3868	0.076*
C6	0.06523 (15)	0.3289 (3)	0.58344 (12)	0.0562 (6)
H6	0.0274	0.2823	0.6064	0.067*
C23	0.01550 (14)	0.2770 (3)	0.06552 (12)	0.0587 (6)
H23A	−0.0251	0.2010	0.0429	0.070*
H23B	0.0330	0.3337	0.0267	0.070*
C19	0.18501 (16)	−0.1081 (3)	0.31565 (13)	0.0611 (6)
H19	0.1809	−0.2113	0.3273	0.073*
C30	−0.16798 (15)	0.3466 (3)	0.04937 (13)	0.0584 (6)
H30	−0.1566	0.2444	0.0410	0.070*
C29	−0.24709 (15)	0.4006 (3)	0.02398 (14)	0.0625 (7)
H29	−0.2884	0.3358	−0.0014	0.075*
C27	−0.20378 (18)	0.6475 (3)	0.07271 (14)	0.0682 (7)
H27	−0.2159	0.7495	0.0807	0.082*
C2	0.19346 (16)	0.4570 (3)	0.59173 (14)	0.0636 (7)
H2	0.2423	0.4964	0.6203	0.076*
C13	−0.11773 (16)	0.0373 (3)	0.29201 (14)	0.0723 (8)
H13A	−0.0963	−0.0271	0.3342	0.087*
H13B	−0.1368	−0.0255	0.2488	0.087*
H13C	−0.1627	0.0970	0.3012	0.087*
C22	0.12756 (17)	0.0882 (3)	0.08263 (14)	0.0740 (8)
H22A	0.0902	0.0055	0.0647	0.089*
H22B	0.1737	0.0497	0.1191	0.089*
H22C	0.1465	0.1322	0.0419	0.089*
H1N	0.0456 (17)	−0.198 (3)	0.2158 (15)	0.082 (9)*

	U11	U22	U33	U12	U13	U23
Cl1	0.1218 (6)	0.0714 (4)	0.0461 (3)	−0.0034 (4)	−0.0010 (4)	−0.0014 (3)
Cl2	0.0795 (5)	0.1069 (6)	0.0911 (5)	0.0369 (5)	0.0232 (4)	0.0095 (5)
N1	0.0503 (10)	0.0402 (10)	0.0473 (10)	−0.0088 (8)	0.0085 (8)	0.0028 (8)
O1	0.0828 (12)	0.0474 (9)	0.0543 (10)	−0.0240 (9)	0.0167 (8)	−0.0025 (8)
C8	0.0432 (11)	0.0390 (11)	0.0447 (11)	0.0002 (10)	0.0124 (9)	−0.0023 (10)
F1	0.0623 (9)	0.0975 (12)	0.0743 (9)	−0.0097 (9)	−0.0015 (7)	0.0029 (9)
N3	0.0734 (15)	0.0359 (11)	0.0717 (14)	−0.0051 (11)	0.0170 (11)	−0.0048 (11)
C12	0.0506 (12)	0.0472 (13)	0.0442 (12)	−0.0026 (11)	0.0113 (10)	0.0036 (10)
C9	0.0455 (12)	0.0373 (12)	0.0486 (12)	−0.0024 (10)	0.0127 (10)	−0.0008 (10)
O2	0.0784 (12)	0.0592 (11)	0.0723 (11)	−0.0169 (10)	0.0025 (10)	−0.0181 (9)
N2	0.0589 (11)	0.0572 (12)	0.0434 (10)	−0.0002 (10)	0.0162 (9)	−0.0012 (9)
C20	0.0606 (15)	0.0426 (12)	0.0537 (13)	0.0031 (12)	0.0205 (12)	−0.0020 (11)
C15	0.0500 (12)	0.0434 (12)	0.0432 (11)	−0.0005 (11)	0.0154 (10)	−0.0017 (10)
C5	0.0487 (13)	0.0594 (15)	0.0467 (13)	0.0006 (11)	0.0077 (10)	−0.0037 (11)
C10	0.0478 (12)	0.0371 (11)	0.0413 (11)	−0.0046 (10)	0.0104 (9)	−0.0008 (9)
C11	0.0487 (12)	0.0422 (12)	0.0459 (12)	−0.0047 (10)	0.0086 (10)	0.0018 (10)
C4	0.0475 (12)	0.0403 (12)	0.0463 (12)	0.0032 (10)	0.0082 (10)	−0.0038 (10)
C17	0.0491 (14)	0.0706 (17)	0.0517 (13)	−0.0016 (13)	0.0125 (11)	−0.0044 (13)
C25	0.0652 (14)	0.0380 (12)	0.0396 (11)	−0.0039 (11)	0.0125 (11)	0.0057 (9)
C28	0.0681 (16)	0.0607 (16)	0.0515 (14)	0.0134 (14)	0.0193 (12)	0.0090 (12)
C24	0.0575 (13)	0.0437 (12)	0.0442 (12)	−0.0103 (11)	0.0101 (10)	0.0011 (10)
C14	0.0555 (13)	0.0399 (12)	0.0442 (12)	−0.0048 (10)	0.0124 (10)	−0.0037 (10)
C16	0.0539 (13)	0.0502 (13)	0.0493 (12)	−0.0017 (12)	0.0173 (11)	−0.0004 (11)
C26	0.0792 (17)	0.0440 (13)	0.0509 (13)	−0.0030 (13)	0.0103 (12)	−0.0024 (11)
C1	0.0786 (17)	0.0429 (13)	0.0457 (12)	0.0062 (13)	0.0019 (12)	−0.0018 (11)
C3	0.0594 (15)	0.0506 (13)	0.0575 (15)	−0.0081 (12)	0.0087 (12)	−0.0037 (12)
C7	0.0472 (12)	0.0440 (12)	0.0508 (13)	−0.0016 (10)	0.0142 (10)	−0.0016 (10)
C21	0.0652 (16)	0.0441 (14)	0.0570 (14)	−0.0068 (12)	0.0172 (13)	−0.0107 (12)
C18	0.0652 (16)	0.0706 (18)	0.0539 (14)	0.0174 (14)	0.0151 (12)	0.0086 (13)
C6	0.0616 (15)	0.0574 (15)	0.0500 (13)	0.0031 (12)	0.0137 (12)	0.0013 (12)
C23	0.0654 (15)	0.0668 (16)	0.0437 (12)	−0.0009 (13)	0.0123 (11)	0.0007 (12)
C19	0.0769 (17)	0.0476 (14)	0.0632 (15)	0.0096 (14)	0.0250 (13)	0.0059 (13)
C30	0.0679 (16)	0.0395 (13)	0.0615 (14)	−0.0006 (12)	0.0015 (12)	0.0005 (11)
C29	0.0621 (16)	0.0540 (15)	0.0657 (15)	−0.0020 (13)	0.0029 (13)	0.0061 (13)
C27	0.095 (2)	0.0495 (15)	0.0602 (15)	0.0153 (15)	0.0188 (15)	−0.0031 (13)
C2	0.0702 (16)	0.0525 (14)	0.0582 (15)	−0.0077 (13)	−0.0056 (13)	−0.0046 (12)
C13	0.0798 (18)	0.0659 (17)	0.0662 (16)	−0.0311 (15)	0.0068 (14)	0.0128 (14)
C22	0.0839 (19)	0.0835 (19)	0.0605 (15)	0.0118 (16)	0.0286 (14)	−0.0052 (14)

Cl1—C1	1.739 (2)	C17—C16	1.375 (3)
Cl2—C28	1.746 (3)	C25—C26	1.386 (3)
N1—C12	1.450 (3)	C25—C30	1.388 (3)
N1—C11	1.454 (3)	C25—C24	1.510 (3)
N1—C13	1.456 (3)	C28—C29	1.366 (3)
O1—C9	1.218 (2)	C28—C27	1.367 (4)
C8—C7	1.345 (3)	C24—C23	1.517 (3)
C8—C9	1.494 (3)	C24—H24	0.9800
C8—C12	1.502 (3)	C14—C21	1.572 (3)
F1—C17	1.365 (3)	C16—H16	0.9300
N3—C21	1.358 (3)	C26—C27	1.379 (3)
N3—C20	1.397 (3)	C26—H26	0.9300
N3—H1N	0.84 (3)	C1—C6	1.372 (3)
C12—H12A	0.9700	C1—C2	1.374 (4)
C12—H12B	0.9700	C3—C2	1.379 (3)
C9—C10	1.542 (3)	C3—H3	0.9300
O2—C21	1.219 (3)	C7—H7	0.9300
N2—C23	1.457 (3)	C18—C19	1.387 (3)
N2—C22	1.461 (3)	C18—H18	0.9300
N2—C14	1.469 (3)	C6—H6	0.9300
C20—C19	1.371 (3)	C23—H23A	0.9700
C20—C15	1.393 (3)	C23—H23B	0.9700
C15—C16	1.380 (3)	C19—H19	0.9300
C15—C14	1.513 (3)	C30—C29	1.379 (3)
C5—C6	1.380 (3)	C30—H30	0.9300
C5—C4	1.387 (3)	C29—H29	0.9300
C5—H5	0.9300	C27—H27	0.9300
C10—C11	1.537 (3)	C2—H2	0.9300
C10—C24	1.568 (3)	C13—H13A	0.9600
C10—C14	1.587 (3)	C13—H13B	0.9600
C11—H11A	0.9700	C13—H13C	0.9600
C11—H11B	0.9700	C22—H22A	0.9600
C4—C3	1.396 (3)	C22—H22B	0.9600
C4—C7	1.461 (3)	C22—H22C	0.9600
C17—C18	1.364 (4)
C12—N1—C11	111.05 (16)	C15—C14—C21	100.68 (17)
C12—N1—C13	110.34 (18)	N2—C14—C10	102.30 (16)
C11—N1—C13	112.83 (17)	C15—C14—C10	119.19 (17)
C7—C8—C9	116.53 (19)	C21—C14—C10	112.84 (17)
C7—C8—C12	124.05 (19)	C17—C16—C15	117.6 (2)
C9—C8—C12	119.41 (17)	C17—C16—H16	121.2
C21—N3—C20	112.2 (2)	C15—C16—H16	121.2
C21—N3—H1N	123.9 (19)	C27—C26—C25	121.8 (2)
C20—N3—H1N	123.5 (19)	C27—C26—H26	119.1
N1—C12—C8	113.68 (17)	C25—C26—H26	119.1
N1—C12—H12A	108.8	C6—C1—C2	120.7 (2)
C8—C12—H12A	108.8	C6—C1—Cl1	119.1 (2)
N1—C12—H12B	108.8	C2—C1—Cl1	120.16 (19)
C8—C12—H12B	108.8	C2—C3—C4	122.0 (2)
H12A—C12—H12B	107.7	C2—C3—H3	119.0
O1—C9—C8	120.96 (19)	C4—C3—H3	119.0
O1—C9—C10	121.42 (19)	C8—C7—C4	130.8 (2)
C8—C9—C10	117.59 (18)	C8—C7—H7	114.6
C23—N2—C22	114.55 (18)	C4—C7—H7	114.6
C23—N2—C14	106.82 (16)	O2—C21—N3	125.6 (2)
C22—N2—C14	116.15 (19)	O2—C21—C14	126.4 (2)
C19—C20—C15	122.4 (2)	N3—C21—C14	107.9 (2)
C19—C20—N3	128.1 (2)	C17—C18—C19	119.3 (2)
C15—C20—N3	109.5 (2)	C17—C18—H18	120.3
C16—C15—C20	119.3 (2)	C19—C18—H18	120.3
C16—C15—C14	130.7 (2)	C1—C6—C5	119.1 (2)
C20—C15—C14	109.71 (19)	C1—C6—H6	120.4
C6—C5—C4	122.3 (2)	C5—C6—H6	120.4
C6—C5—H5	118.8	N2—C23—C24	102.47 (17)
C4—C5—H5	118.8	N2—C23—H23A	111.3
C11—C10—C9	105.19 (16)	C24—C23—H23A	111.3
C11—C10—C24	114.90 (17)	N2—C23—H23B	111.3
C9—C10—C24	110.89 (17)	C24—C23—H23B	111.3
C11—C10—C14	110.74 (16)	H23A—C23—H23B	109.2
C9—C10—C14	111.11 (16)	C20—C19—C18	118.0 (2)
C24—C10—C14	104.14 (16)	C20—C19—H19	121.0
N1—C11—C10	107.35 (16)	C18—C19—H19	121.0
N1—C11—H11A	110.2	C29—C30—C25	121.8 (2)
C10—C11—H11A	110.2	C29—C30—H30	119.1
N1—C11—H11B	110.2	C25—C30—H30	119.1
C10—C11—H11B	110.2	C28—C29—C30	119.2 (2)
H11A—C11—H11B	108.5	C28—C29—H29	120.4
C5—C4—C3	116.5 (2)	C30—C29—H29	120.4
C5—C4—C7	125.05 (19)	C28—C27—C26	119.2 (2)
C3—C4—C7	118.4 (2)	C28—C27—H27	120.4
C18—C17—F1	118.6 (2)	C26—C27—H27	120.4
C18—C17—C16	123.5 (2)	C1—C2—C3	119.3 (2)
F1—C17—C16	118.0 (2)	C1—C2—H2	120.4
C26—C25—C30	117.0 (2)	C3—C2—H2	120.4
C26—C25—C24	120.2 (2)	N1—C13—H13A	109.5
C30—C25—C24	122.8 (2)	N1—C13—H13B	109.5
C29—C28—C27	121.0 (2)	H13A—C13—H13B	109.5
C29—C28—Cl2	118.6 (2)	N1—C13—H13C	109.5
C27—C28—Cl2	120.4 (2)	H13A—C13—H13C	109.5
C25—C24—C23	116.08 (18)	H13B—C13—H13C	109.5
C25—C24—C10	115.64 (17)	N2—C22—H22A	109.5
C23—C24—C10	104.34 (17)	N2—C22—H22B	109.5
C25—C24—H24	106.7	H22A—C22—H22B	109.5
C23—C24—H24	106.7	N2—C22—H22C	109.5
C10—C24—H24	106.7	H22A—C22—H22C	109.5
N2—C14—C15	110.68 (17)	H22B—C22—H22C	109.5
N2—C14—C21	111.43 (17)
C11—N1—C12—C8	−46.9 (2)	C24—C10—C14—N2	15.56 (19)
C13—N1—C12—C8	−172.82 (19)	C11—C10—C14—C15	−98.0 (2)
C7—C8—C12—N1	−162.6 (2)	C9—C10—C14—C15	18.5 (2)
C9—C8—C12—N1	18.2 (3)	C24—C10—C14—C15	137.96 (18)
C7—C8—C9—O1	−17.5 (3)	C11—C10—C14—C21	19.7 (2)
C12—C8—C9—O1	161.9 (2)	C9—C10—C14—C21	136.27 (18)
C7—C8—C9—C10	164.77 (18)	C24—C10—C14—C21	−104.29 (19)
C12—C8—C9—C10	−15.9 (3)	C18—C17—C16—C15	0.3 (3)
C21—N3—C20—C19	−178.2 (2)	F1—C17—C16—C15	−179.82 (18)
C21—N3—C20—C15	−0.7 (3)	C20—C15—C16—C17	−1.4 (3)
C19—C20—C15—C16	2.2 (3)	C14—C15—C16—C17	−174.3 (2)
N3—C20—C15—C16	−175.45 (19)	C30—C25—C26—C27	1.3 (3)
C19—C20—C15—C14	176.5 (2)	C24—C25—C26—C27	−178.5 (2)
N3—C20—C15—C14	−1.1 (2)	C5—C4—C3—C2	1.5 (3)
O1—C9—C10—C11	−139.5 (2)	C7—C4—C3—C2	179.8 (2)
C8—C9—C10—C11	38.2 (2)	C9—C8—C7—C4	179.3 (2)
O1—C9—C10—C24	−14.7 (3)	C12—C8—C7—C4	0.0 (4)
C8—C9—C10—C24	163.01 (17)	C5—C4—C7—C8	−18.4 (4)
O1—C9—C10—C14	100.6 (2)	C3—C4—C7—C8	163.5 (2)
C8—C9—C10—C14	−81.7 (2)	C20—N3—C21—O2	177.5 (2)
C12—N1—C11—C10	74.2 (2)	C20—N3—C21—C14	2.2 (3)
C13—N1—C11—C10	−161.35 (19)	N2—C14—C21—O2	−60.5 (3)
C9—C10—C11—N1	−66.3 (2)	C15—C14—C21—O2	−177.9 (2)
C24—C10—C11—N1	171.46 (16)	C10—C14—C21—O2	54.0 (3)
C14—C10—C11—N1	53.8 (2)	N2—C14—C21—N3	114.7 (2)
C6—C5—C4—C3	−1.2 (3)	C15—C14—C21—N3	−2.7 (2)
C6—C5—C4—C7	−179.3 (2)	C10—C14—C21—N3	−130.82 (19)
C26—C25—C24—C23	−138.5 (2)	F1—C17—C18—C19	−179.7 (2)
C30—C25—C24—C23	41.7 (3)	C16—C17—C18—C19	0.2 (4)
C26—C25—C24—C10	98.8 (2)	C2—C1—C6—C5	0.5 (4)
C30—C25—C24—C10	−81.1 (3)	Cl1—C1—C6—C5	178.68 (18)
C11—C10—C24—C25	18.4 (3)	C4—C5—C6—C1	0.2 (4)
C9—C10—C24—C25	−100.7 (2)	C22—N2—C23—C24	176.68 (19)
C14—C10—C24—C25	139.74 (18)	C14—N2—C23—C24	46.6 (2)
C11—C10—C24—C23	−110.3 (2)	C25—C24—C23—N2	−162.38 (18)
C9—C10—C24—C23	130.57 (18)	C10—C24—C23—N2	−33.9 (2)
C14—C10—C24—C23	11.0 (2)	C15—C20—C19—C18	−1.7 (3)
C23—N2—C14—C15	−166.58 (18)	N3—C20—C19—C18	175.5 (2)
C22—N2—C14—C15	64.2 (2)	C17—C18—C19—C20	0.5 (3)
C23—N2—C14—C21	82.3 (2)	C26—C25—C30—C29	−0.8 (3)
C22—N2—C14—C21	−46.9 (3)	C24—C25—C30—C29	179.1 (2)
C23—N2—C14—C10	−38.6 (2)	C27—C28—C29—C30	0.9 (4)
C22—N2—C14—C10	−167.77 (18)	Cl2—C28—C29—C30	179.04 (18)
C16—C15—C14—N2	57.8 (3)	C25—C30—C29—C28	−0.3 (4)
C20—C15—C14—N2	−115.70 (19)	C29—C28—C27—C26	−0.4 (4)
C16—C15—C14—C21	175.7 (2)	Cl2—C28—C27—C26	−178.46 (18)
C20—C15—C14—C21	2.3 (2)	C25—C26—C27—C28	−0.8 (4)
C16—C15—C14—C10	−60.4 (3)	C6—C1—C2—C3	−0.2 (4)
C20—C15—C14—C10	126.16 (19)	Cl1—C1—C2—C3	−178.34 (19)
C11—C10—C14—N2	139.59 (16)	C4—C3—C2—C1	−0.9 (4)
C9—C10—C14—N2	−103.89 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O2	0.97	2.37	2.968 (3)	119
C23—H23A···O2	0.97	2.58	3.162 (3)	119
C24—H24···O1	0.98	2.26	2.787 (3)	113
N3—H1N···O1i	0.84 (3)	2.50 (3)	3.288 (3)	157 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N⋯O1i	0.84 (3)	2.50 (3)	3.288 (3)	157 (3)

Symmetry code: (i) .