Methyl 3'-(2,5-di-methyl-benz-yl)-1'-methyl-2-oxo-4'-phenyl-spiro-[indoline-3,2'-pyrrolidine]-3'-carboxyl-ate chloro-form monosolvate.

In the title solvate, C29H30N2O3·CHCl3, the dihedral angle between the indole ring system (r.m.s. deviation = 0.050 Å) and the 4-methyl-pyrrolidine ring is 88.88 (8)°. The latter ring adopts an envelope conformation with the N atom as the flap. Its mean plane makes dihedral angles of 86.94 (11) and 42.08 (9)° with the phenyl and di-methyl-benzene rings, respectively. The mol-ecular conformation is stabilized by intra-molecular C-H⋯O hydrogen bonds, which generate S(6) and S(9) ring motifs. The chloro-form solvent mol-ecule is linked to the organic mol-ecule by a C-H⋯O hydrogen bond involving the carbonyl O atom of the carboxyl-ate group. In the crystal, mol-ecules are linked via bifurcated N-H⋯(N,O) and C-H⋯O hydrogen bonds, forming chains propagating along [001].

Related literature

For the biological activity of spiro compounds and oxindole derivatives, see: Bhattacharya et al. (1982 ▶); Chande et al. (2005 ▶); Glover et al. (1998 ▶). For a related crystal structure, see: Karthikeyan et al. (2014 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For graph-set motif notation, see: Bernstein et al. (1995 ▶). For bond-length distortions in small rings, see: Allen (1981 ▶).

Experimental

Crystal data

C29H30N2O3·CHCl3

M = 573.92

Monoclinic,

a = 12.9164 (4) Å

b = 17.6167 (5) Å

c = 12.4548 (5) Å

β = 98.135 (2)°

V = 2805.50 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 293 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

32563 measured reflections

8093 independent reflections

4986 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.161

S = 1.01

8093 reflections

347 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814004073/su2703sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814004073/su2703Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814004073/su2703Isup3.cml

CCDC reference: 988124

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

C29H30N2O3·CHCl3	F(000) = 1200
Mr = 573.92	Dx = 1.359 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8093 reflections
a = 12.9164 (4) Å	θ = 2.0–30.0°
b = 17.6167 (5) Å	µ = 0.36 mm−1
c = 12.4548 (5) Å	T = 293 K
β = 98.135 (2)°	Block, colourless
V = 2805.50 (16) Å3	0.35 × 0.30 × 0.25 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	4986 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
Graphite monochromator	θmax = 30.0°, θmin = 2.0°
ω scans	h = −18→15
32563 measured reflections	k = −24→17
8093 independent reflections	l = −16→17

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) = 0.161	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0743P)2 + 0.8771P] where P = (Fo2 + 2Fc2)/3
8093 reflections	(Δ/σ)max = 0.029
347 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.46 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
C1	0.52972 (18)	0.16392 (14)	0.1611 (2)	0.0606 (6)
H1	0.5616	0.1446	0.1045	0.073*
C2	0.4214 (2)	0.16690 (18)	0.1514 (3)	0.0870 (10)
H2	0.3813	0.1492	0.0884	0.104*
C3	0.3732 (2)	0.19554 (17)	0.2334 (3)	0.0844 (10)
H3	0.3006	0.1969	0.2265	0.101*
C4	0.43157 (18)	0.22214 (14)	0.3255 (3)	0.0670 (7)
H4	0.3987	0.2417	0.3813	0.080*
C5	0.54030 (15)	0.22008 (11)	0.33620 (19)	0.0473 (5)
H5	0.5796	0.2393	0.3986	0.057*
C6	0.59068 (14)	0.18961 (10)	0.25467 (16)	0.0391 (4)
C7	0.70826 (13)	0.19113 (9)	0.25662 (13)	0.0300 (3)
H7	0.7220	0.1678	0.1886	0.036*
C8	0.74566 (13)	0.27309 (9)	0.25403 (14)	0.0319 (3)
H8A	0.7355	0.2928	0.1805	0.038*
H8B	0.7086	0.3053	0.2991	0.038*
C9	0.86380 (12)	0.21922 (9)	0.39155 (12)	0.0269 (3)
C10	0.82724 (13)	0.25825 (9)	0.49252 (13)	0.0309 (3)
C11	0.99571 (13)	0.21963 (10)	0.54390 (14)	0.0347 (4)
C12	1.09263 (16)	0.20958 (12)	0.60490 (17)	0.0482 (5)
H12	1.1043	0.2224	0.6780	0.058*
C13	1.17168 (16)	0.17983 (13)	0.5537 (2)	0.0540 (5)
H13	1.2374	0.1715	0.5932	0.065*
C14	1.15450 (15)	0.16239 (12)	0.44510 (19)	0.0497 (5)
H14	1.2091	0.1434	0.4117	0.060*
C15	1.05653 (14)	0.17275 (10)	0.38447 (16)	0.0391 (4)
H15	1.0456	0.1616	0.3108	0.047*
C16	0.97590 (13)	0.19984 (9)	0.43528 (13)	0.0301 (3)
C17	0.78538 (12)	0.15185 (9)	0.35030 (12)	0.0272 (3)
C18	0.73755 (13)	0.11476 (9)	0.44370 (14)	0.0324 (4)
H18A	0.7936	0.1058	0.5028	0.039*
H18B	0.6903	0.1511	0.4693	0.039*
C19	0.67848 (13)	0.04089 (9)	0.42034 (15)	0.0356 (4)
C20	0.64281 (14)	0.01636 (10)	0.31604 (17)	0.0418 (4)
H20	0.6602	0.0446	0.2581	0.050*
C21	0.58202 (15)	−0.04865 (11)	0.2939 (2)	0.0506 (5)
C22	0.56029 (16)	−0.09077 (12)	0.3815 (2)	0.0592 (6)
H22	0.5208	−0.1349	0.3698	0.071*
C23	0.59634 (16)	−0.06826 (12)	0.4854 (2)	0.0573 (6)
H23	0.5806	−0.0978	0.5429	0.069*
C24	0.65561 (14)	−0.00280 (11)	0.50774 (18)	0.0443 (5)
C25	0.85308 (13)	0.09330 (9)	0.30117 (14)	0.0314 (3)
C26	0.96441 (19)	−0.01230 (12)	0.3421 (2)	0.0563 (6)
H26A	0.9259	−0.0453	0.2896	0.084*
H26B	0.9945	−0.0414	0.4039	0.084*
H26C	1.0191	0.0123	0.3103	0.084*
C27	0.90549 (16)	0.34317 (11)	0.31638 (17)	0.0454 (5)
H27A	0.8690	0.3715	0.3651	0.068*
H27B	0.9024	0.3701	0.2490	0.068*
H27C	0.9772	0.3368	0.3479	0.068*
C28	0.5391 (2)	−0.06896 (15)	0.1793 (2)	0.0740 (8)
H28A	0.4752	−0.0969	0.1785	0.111*
H28B	0.5891	−0.0995	0.1487	0.111*
H28C	0.5256	−0.0234	0.1373	0.111*
C29	0.69211 (19)	0.01897 (14)	0.6230 (2)	0.0604 (6)
H29A	0.6638	−0.0158	0.6706	0.091*
H29B	0.6689	0.0695	0.6358	0.091*
H29C	0.7671	0.0172	0.6366	0.091*
C30	0.8351 (2)	−0.03717 (16)	0.0148 (2)	0.0727 (7)
H30	0.8775	−0.0035	0.0660	0.087*
N1	0.85668 (11)	0.26899 (7)	0.29684 (11)	0.0297 (3)
N2	0.90658 (11)	0.25256 (9)	0.57607 (12)	0.0391 (4)
H2A	0.9025	0.2674	0.6411	0.047*
O1	0.74367 (10)	0.28839 (7)	0.49619 (10)	0.0406 (3)
O2	0.87103 (11)	0.09300 (8)	0.20917 (10)	0.0470 (3)
O3	0.89518 (10)	0.04398 (7)	0.37572 (10)	0.0376 (3)
Cl1	0.80296 (6)	−0.11741 (5)	0.08605 (8)	0.0992 (3)
Cl2	0.72435 (8)	0.01165 (5)	−0.03976 (10)	0.1107 (3)
Cl3	0.91063 (9)	−0.06436 (6)	−0.08484 (8)	0.1116 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0494 (12)	0.0582 (13)	0.0670 (15)	−0.0072 (10)	−0.0171 (11)	0.0041 (11)
C2	0.0539 (16)	0.086 (2)	0.108 (3)	−0.0188 (15)	−0.0341 (16)	0.0200 (18)
C3	0.0336 (12)	0.0785 (19)	0.137 (3)	−0.0047 (12)	−0.0028 (16)	0.0423 (19)
C4	0.0418 (12)	0.0548 (13)	0.108 (2)	0.0071 (10)	0.0222 (13)	0.0316 (14)
C5	0.0376 (10)	0.0399 (10)	0.0651 (14)	0.0012 (8)	0.0102 (9)	0.0142 (9)
C6	0.0340 (9)	0.0296 (8)	0.0517 (11)	−0.0008 (7)	−0.0013 (8)	0.0098 (8)
C7	0.0339 (8)	0.0287 (8)	0.0267 (8)	−0.0002 (6)	0.0018 (6)	0.0003 (6)
C8	0.0367 (9)	0.0299 (8)	0.0287 (8)	0.0003 (7)	0.0039 (7)	0.0051 (6)
C9	0.0298 (8)	0.0286 (7)	0.0228 (7)	−0.0004 (6)	0.0055 (6)	−0.0013 (6)
C10	0.0341 (9)	0.0312 (8)	0.0283 (8)	−0.0014 (7)	0.0072 (7)	−0.0031 (6)
C11	0.0317 (8)	0.0382 (9)	0.0341 (9)	−0.0009 (7)	0.0044 (7)	−0.0018 (7)
C12	0.0415 (11)	0.0599 (13)	0.0399 (11)	0.0017 (9)	−0.0056 (8)	−0.0038 (9)
C13	0.0344 (10)	0.0611 (13)	0.0632 (14)	0.0037 (9)	−0.0046 (9)	−0.0019 (11)
C14	0.0335 (10)	0.0517 (12)	0.0653 (14)	0.0056 (8)	0.0119 (9)	−0.0041 (10)
C15	0.0374 (9)	0.0410 (10)	0.0402 (10)	0.0003 (8)	0.0100 (8)	−0.0042 (8)
C16	0.0306 (8)	0.0298 (8)	0.0301 (8)	−0.0030 (6)	0.0055 (6)	−0.0002 (6)
C17	0.0314 (8)	0.0250 (7)	0.0253 (8)	−0.0013 (6)	0.0046 (6)	0.0003 (6)
C18	0.0356 (9)	0.0304 (8)	0.0324 (9)	−0.0007 (7)	0.0090 (7)	0.0043 (6)
C19	0.0292 (8)	0.0284 (8)	0.0502 (11)	0.0026 (6)	0.0093 (7)	0.0089 (7)
C20	0.0380 (10)	0.0307 (9)	0.0562 (12)	−0.0020 (7)	0.0049 (8)	0.0039 (8)
C21	0.0340 (10)	0.0314 (9)	0.0848 (16)	0.0004 (8)	0.0029 (10)	−0.0025 (10)
C22	0.0367 (10)	0.0332 (10)	0.107 (2)	−0.0054 (8)	0.0098 (12)	0.0091 (12)
C23	0.0420 (11)	0.0420 (11)	0.0911 (19)	0.0000 (9)	0.0208 (12)	0.0279 (11)
C24	0.0349 (9)	0.0375 (9)	0.0637 (13)	0.0059 (8)	0.0178 (9)	0.0191 (9)
C25	0.0345 (8)	0.0276 (8)	0.0318 (9)	−0.0022 (7)	0.0036 (7)	−0.0021 (6)
C26	0.0637 (14)	0.0415 (11)	0.0639 (14)	0.0206 (10)	0.0101 (11)	−0.0004 (10)
C27	0.0527 (11)	0.0331 (9)	0.0501 (12)	−0.0124 (8)	0.0055 (9)	0.0033 (8)
C28	0.0675 (16)	0.0518 (14)	0.097 (2)	−0.0107 (12)	−0.0083 (14)	−0.0168 (13)
C29	0.0594 (14)	0.0661 (14)	0.0595 (14)	0.0025 (11)	0.0219 (11)	0.0265 (11)
C30	0.0636 (16)	0.0764 (17)	0.0758 (18)	−0.0125 (13)	0.0022 (13)	−0.0162 (14)
N1	0.0347 (7)	0.0274 (7)	0.0272 (7)	−0.0048 (5)	0.0050 (5)	0.0023 (5)
N2	0.0374 (8)	0.0554 (9)	0.0243 (7)	0.0019 (7)	0.0037 (6)	−0.0096 (6)
O1	0.0380 (7)	0.0472 (7)	0.0373 (7)	0.0077 (6)	0.0084 (5)	−0.0086 (5)
O2	0.0607 (9)	0.0490 (8)	0.0330 (7)	0.0132 (7)	0.0124 (6)	−0.0031 (6)
O3	0.0426 (7)	0.0309 (6)	0.0394 (7)	0.0085 (5)	0.0064 (5)	0.0036 (5)
Cl1	0.0716 (5)	0.1114 (6)	0.1077 (7)	−0.0031 (4)	−0.0107 (4)	0.0367 (5)
Cl2	0.0970 (6)	0.0791 (5)	0.1532 (9)	0.0107 (4)	0.0078 (6)	0.0290 (5)
Cl3	0.1246 (8)	0.1139 (7)	0.1039 (7)	−0.0108 (6)	0.0420 (6)	−0.0332 (5)

C1—C6	1.386 (3)	C17—C18	1.538 (2)
C1—C2	1.388 (4)	C18—C19	1.516 (2)
C1—H1	0.9300	C18—H18A	0.9700
C2—C3	1.366 (5)	C18—H18B	0.9700
C2—H2	0.9300	C19—C20	1.385 (3)
C3—C4	1.363 (5)	C19—C24	1.398 (3)
C3—H3	0.9300	C20—C21	1.394 (3)
C4—C5	1.392 (3)	C20—H20	0.9300
C4—H4	0.9300	C21—C22	1.380 (3)
C5—C6	1.389 (3)	C21—C28	1.500 (4)
C5—H5	0.9300	C22—C23	1.371 (4)
C6—C7	1.516 (2)	C22—H22	0.9300
C7—C8	1.524 (2)	C23—C24	1.390 (3)
C7—C17	1.582 (2)	C23—H23	0.9300
C7—H7	0.9800	C24—C29	1.497 (3)
C8—N1	1.459 (2)	C25—O2	1.201 (2)
C8—H8A	0.9700	C25—O3	1.330 (2)
C8—H8B	0.9700	C26—O3	1.437 (2)
C9—N1	1.462 (2)	C26—H26A	0.9600
C9—C16	1.512 (2)	C26—H26B	0.9600
C9—C10	1.564 (2)	C26—H26C	0.9600
C9—C17	1.597 (2)	C27—N1	1.456 (2)
C10—O1	1.210 (2)	C27—H27A	0.9600
C10—N2	1.357 (2)	C27—H27B	0.9600
C11—C12	1.381 (3)	C27—H27C	0.9600
C11—C16	1.385 (2)	C28—H28A	0.9600
C11—N2	1.397 (2)	C28—H28B	0.9600
C12—C13	1.382 (3)	C28—H28C	0.9600
C12—H12	0.9300	C29—H29A	0.9600
C13—C14	1.374 (3)	C29—H29B	0.9600
C13—H13	0.9300	C29—H29C	0.9600
C14—C15	1.391 (3)	C30—Cl2	1.724 (3)
C14—H14	0.9300	C30—Cl1	1.750 (3)
C15—C16	1.378 (2)	C30—Cl3	1.751 (3)
C15—H15	0.9300	C30—H30	0.9800
C17—C25	1.534 (2)	N2—H2A	0.8600
C6—C1—C2	120.4 (3)	C19—C18—H18A	107.9
C6—C1—H1	119.8	C17—C18—H18A	107.9
C2—C1—H1	119.8	C19—C18—H18B	107.9
C3—C2—C1	120.6 (3)	C17—C18—H18B	107.9
C3—C2—H2	119.7	H18A—C18—H18B	107.2
C1—C2—H2	119.7	C20—C19—C24	118.66 (17)
C4—C3—C2	120.0 (2)	C20—C19—C18	122.66 (16)
C4—C3—H3	120.0	C24—C19—C18	118.63 (17)
C2—C3—H3	120.0	C19—C20—C21	123.04 (19)
C3—C4—C5	120.1 (3)	C19—C20—H20	118.5
C3—C4—H4	120.0	C21—C20—H20	118.5
C5—C4—H4	120.0	C22—C21—C20	117.2 (2)
C6—C5—C4	120.7 (2)	C22—C21—C28	122.3 (2)
C6—C5—H5	119.6	C20—C21—C28	120.4 (2)
C4—C5—H5	119.6	C23—C22—C21	120.71 (19)
C1—C6—C5	118.11 (19)	C23—C22—H22	119.6
C1—C6—C7	117.89 (19)	C21—C22—H22	119.6
C5—C6—C7	123.60 (17)	C22—C23—C24	122.2 (2)
C6—C7—C8	109.65 (14)	C22—C23—H23	118.9
C6—C7—C17	121.93 (14)	C24—C23—H23	118.9
C8—C7—C17	105.16 (13)	C23—C24—C19	118.2 (2)
C6—C7—H7	106.4	C23—C24—C29	119.59 (19)
C8—C7—H7	106.4	C19—C24—C29	122.23 (18)
C17—C7—H7	106.4	O2—C25—O3	123.23 (16)
N1—C8—C7	104.09 (13)	O2—C25—C17	125.55 (15)
N1—C8—H8A	110.9	O3—C25—C17	111.12 (14)
C7—C8—H8A	110.9	O3—C26—H26A	109.5
N1—C8—H8B	110.9	O3—C26—H26B	109.5
C7—C8—H8B	110.9	H26A—C26—H26B	109.5
H8A—C8—H8B	109.0	O3—C26—H26C	109.5
N1—C9—C16	111.94 (13)	H26A—C26—H26C	109.5
N1—C9—C10	113.17 (13)	H26B—C26—H26C	109.5
C16—C9—C10	101.09 (12)	N1—C27—H27A	109.5
N1—C9—C17	102.79 (12)	N1—C27—H27B	109.5
C16—C9—C17	118.65 (13)	H27A—C27—H27B	109.5
C10—C9—C17	109.60 (12)	N1—C27—H27C	109.5
O1—C10—N2	125.77 (16)	H27A—C27—H27C	109.5
O1—C10—C9	126.59 (15)	H27B—C27—H27C	109.5
N2—C10—C9	107.64 (14)	C21—C28—H28A	109.5
C12—C11—C16	122.20 (17)	C21—C28—H28B	109.5
C12—C11—N2	127.95 (17)	H28A—C28—H28B	109.5
C16—C11—N2	109.79 (15)	C21—C28—H28C	109.5
C11—C12—C13	117.80 (19)	H28A—C28—H28C	109.5
C11—C12—H12	121.1	H28B—C28—H28C	109.5
C13—C12—H12	121.1	C24—C29—H29A	109.5
C14—C13—C12	120.82 (19)	C24—C29—H29B	109.5
C14—C13—H13	119.6	H29A—C29—H29B	109.5
C12—C13—H13	119.6	C24—C29—H29C	109.5
C13—C14—C15	120.86 (19)	H29A—C29—H29C	109.5
C13—C14—H14	119.6	H29B—C29—H29C	109.5
C15—C14—H14	119.6	Cl2—C30—Cl1	111.11 (15)
C16—C15—C14	118.99 (18)	Cl2—C30—Cl3	111.84 (17)
C16—C15—H15	120.5	Cl1—C30—Cl3	109.54 (16)
C14—C15—H15	120.5	Cl2—C30—H30	108.1
C15—C16—C11	119.24 (16)	Cl1—C30—H30	108.1
C15—C16—C9	131.30 (15)	Cl3—C30—H30	108.1
C11—C16—C9	109.27 (14)	C27—N1—C8	113.35 (14)
C25—C17—C18	109.19 (13)	C27—N1—C9	115.28 (14)
C25—C17—C7	109.56 (13)	C8—N1—C9	105.71 (12)
C18—C17—C7	117.73 (13)	C10—N2—C11	111.97 (14)
C25—C17—C9	104.86 (12)	C10—N2—H2A	124.0
C18—C17—C9	112.13 (13)	C11—N2—H2A	124.0
C7—C17—C9	102.51 (12)	C25—O3—C26	117.19 (15)
C19—C18—C17	117.69 (15)
C6—C1—C2—C3	0.4 (4)	C10—C9—C17—C25	−149.46 (13)
C1—C2—C3—C4	0.6 (4)	N1—C9—C17—C18	−151.71 (13)
C2—C3—C4—C5	−0.1 (4)	C16—C9—C17—C18	84.19 (17)
C3—C4—C5—C6	−1.4 (3)	C10—C9—C17—C18	−31.11 (17)
C2—C1—C6—C5	−1.8 (3)	N1—C9—C17—C7	−24.50 (14)
C2—C1—C6—C7	−174.9 (2)	C16—C9—C17—C7	−148.60 (14)
C4—C5—C6—C1	2.3 (3)	C10—C9—C17—C7	96.10 (14)
C4—C5—C6—C7	174.93 (18)	C25—C17—C18—C19	−52.72 (19)
C1—C6—C7—C8	109.52 (19)	C7—C17—C18—C19	72.97 (19)
C5—C6—C7—C8	−63.2 (2)	C9—C17—C18—C19	−168.48 (14)
C1—C6—C7—C17	−127.14 (19)	C17—C18—C19—C20	−17.2 (2)
C5—C6—C7—C17	60.2 (2)	C17—C18—C19—C24	165.28 (15)
C6—C7—C8—N1	159.17 (14)	C24—C19—C20—C21	2.2 (3)
C17—C7—C8—N1	26.43 (16)	C18—C19—C20—C21	−175.26 (17)
N1—C9—C10—O1	55.2 (2)	C19—C20—C21—C22	−2.1 (3)
C16—C9—C10—O1	175.02 (17)	C19—C20—C21—C28	175.4 (2)
C17—C9—C10—O1	−58.9 (2)	C20—C21—C22—C23	0.9 (3)
N1—C9—C10—N2	−124.66 (15)	C28—C21—C22—C23	−176.5 (2)
C16—C9—C10—N2	−4.79 (17)	C21—C22—C23—C24	0.1 (3)
C17—C9—C10—N2	121.26 (15)	C22—C23—C24—C19	0.0 (3)
C16—C11—C12—C13	1.1 (3)	C22—C23—C24—C29	179.6 (2)
N2—C11—C12—C13	−175.89 (19)	C20—C19—C24—C23	−1.1 (3)
C11—C12—C13—C14	1.3 (3)	C18—C19—C24—C23	176.45 (16)
C12—C13—C14—C15	−1.3 (3)	C20—C19—C24—C29	179.27 (18)
C13—C14—C15—C16	−1.0 (3)	C18—C19—C24—C29	−3.1 (3)
C14—C15—C16—C11	3.2 (3)	C18—C17—C25—O2	152.45 (17)
C14—C15—C16—C9	177.68 (17)	C7—C17—C25—O2	22.2 (2)
C12—C11—C16—C15	−3.3 (3)	C9—C17—C25—O2	−87.22 (19)
N2—C11—C16—C15	174.10 (16)	C18—C17—C25—O3	−30.95 (18)
C12—C11—C16—C9	−178.93 (17)	C7—C17—C25—O3	−161.22 (13)
N2—C11—C16—C9	−1.49 (19)	C9—C17—C25—O3	89.38 (15)
N1—C9—C16—C15	−50.4 (2)	C7—C8—N1—C27	−171.60 (14)
C10—C9—C16—C15	−171.15 (18)	C7—C8—N1—C9	−44.41 (16)
C17—C9—C16—C15	69.1 (2)	C16—C9—N1—C27	−62.53 (18)
N1—C9—C16—C11	124.47 (15)	C10—C9—N1—C27	50.92 (19)
C10—C9—C16—C11	3.73 (16)	C17—C9—N1—C27	169.04 (14)
C17—C9—C16—C11	−116.06 (15)	C16—C9—N1—C8	171.44 (13)
C6—C7—C17—C25	122.61 (16)	C10—C9—N1—C8	−75.11 (15)
C8—C7—C17—C25	−111.99 (14)	C17—C9—N1—C8	43.01 (15)
C6—C7—C17—C18	−2.9 (2)	O1—C10—N2—C11	−175.49 (17)
C8—C7—C17—C18	122.51 (15)	C9—C10—N2—C11	4.3 (2)
C6—C7—C17—C9	−126.44 (15)	C12—C11—N2—C10	175.34 (19)
C8—C7—C17—C9	−1.03 (16)	C16—C11—N2—C10	−1.9 (2)
N1—C9—C17—C25	89.93 (14)	O2—C25—O3—C26	−0.7 (3)
C16—C9—C17—C25	−34.17 (17)	C17—C25—O3—C26	−177.36 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1	0.93	2.45	3.292 (2)	151
C18—H18B···O1	0.97	2.52	3.127 (2)	120
C30—H30···O2	0.98	2.47	3.319 (3)	144
N2—H2A···O2i	0.86	2.65	3.252 (2)	128
N2—H2A···N1i	0.86	2.20	2.936 (2)	143
C7—H7···O1ii	0.98	2.57	3.359 (2)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1	0.93	2.45	3.292 (2)	151
C18—H18B⋯O1	0.97	2.52	3.127 (2)	120
C30—H30⋯O2	0.98	2.47	3.319 (3)	144
N2—H2A⋯O2i	0.86	2.65	3.252 (2)	128
N2—H2A⋯N1i	0.86	2.20	2.936 (2)	143
C7—H7⋯O1ii	0.98	2.57	3.359 (2)	138

Symmetry codes: (i) ; (ii) .