Methyl 3'-benzyl-4'-(2,4-di-chloro-phen-yl)-1'-methyl-2-oxo-1-propyl-spiro-[indoline-3,2'-pyrrolidine]-3'-carboxy-l-ate.

In the title compound, C30H30Cl2N2O3, the indole ring system is roughly planar, with a maximum deviation of 0.1039 (18) Å for the carbonyl C atom, and makes a dihedral angle of 86.61 (9)° with the mean plane of the pyrrolidine ring. This spiro pyrrolidine ring adopts an envelope conformation with the N atom at the flap position. The pyrrole ring of the indole ring system adopts a twisted conformation on the C-C(=O) bond. The mol-ecular structure is stabilized by an intra-molecular C-H⋯O hydrogen bond, which generates an S(6) ring motif, and a π-π inter-action [centroid-centroid distance = 3.6577 (12) Å] involving the 2,4-di-chloro-phenyl ring and the benzyl ring. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds, forming C(9) chains running parallel to [10-1].

Related literature

For the biological activity of spiro-pyrrolidine and oxindole derivatives, see: Peddi et al. (2004 ▶); Rajeswaran et al. (1999 ▶). For a related crystal structure, see: Jagadeesan et al. (2013 ▶). For graph-set motif notation, see: Bernstein et al. (1995 ▶). For ring puckering analysis, see: Cremer & Pople (1975 ▶). For bond-length distortions in small rings, see: Allen (1981 ▶).

Experimental

Crystal data

C30H30Cl2N2O3

M = 537.46

Monoclinic,

a = 7.5563 (4) Å

b = 28.8497 (16) Å

c = 12.4274 (8) Å

β = 90.433 (3)°

V = 2709.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 293 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

31802 measured reflections

7794 independent reflections

4985 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.167

S = 1.00

7794 reflections

337 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.58 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/S1600536814002621/su2694sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814002621/su2694Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814002621/su2694Isup3.cml

CCDC reference:

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

C30H30Cl2N2O3	F(000) = 1128
Mr = 537.46	Dx = 1.318 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7794 reflections
a = 7.5563 (4) Å	θ = 2.2–29.9°
b = 28.8497 (16) Å	µ = 0.27 mm−1
c = 12.4274 (8) Å	T = 293 K
β = 90.433 (3)°	Block, colourless
V = 2709.1 (3) Å3	0.35 × 0.30 × 0.25 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	4985 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
Graphite monochromator	θmax = 29.9°, θmin = 2.2°
ω scans	h = −10→7
31802 measured reflections	k = −37→40
7794 independent reflections	l = −17→16

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0918P)2 + 0.3965P] where P = (Fo2 + 2Fc2)/3
7794 reflections	(Δ/σ)max < 0.001
337 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.58 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	0.3859 (2)	0.04008 (6)	0.32495 (15)	0.0424 (4)
C2	0.3770 (3)	−0.00713 (7)	0.34519 (18)	0.0512 (5)
H2	0.3748	−0.0183	0.4153	0.061*
C3	0.3714 (2)	−0.03682 (7)	0.25925 (19)	0.0520 (5)
C4	0.3773 (3)	−0.02096 (7)	0.15521 (18)	0.0509 (5)
H4	0.3762	−0.0416	0.0977	0.061*
C5	0.3851 (2)	0.02637 (6)	0.13764 (16)	0.0441 (4)
H5	0.3897	0.0373	0.0673	0.053*
C6	0.3861 (2)	0.05816 (6)	0.22188 (14)	0.0361 (4)
C7	0.3906 (2)	0.10974 (6)	0.20185 (14)	0.0349 (3)
H7	0.4141	0.1247	0.2713	0.042*
C8	0.5393 (2)	0.12406 (6)	0.12614 (17)	0.0456 (4)
H8A	0.6510	0.1268	0.1645	0.055*
H8B	0.5524	0.1019	0.0680	0.055*
C9	0.2936 (2)	0.16388 (5)	0.05789 (13)	0.0330 (3)
C10	0.2552 (2)	0.13941 (6)	−0.05080 (14)	0.0385 (4)
C11	0.1097 (2)	0.20864 (6)	−0.05612 (13)	0.0358 (4)
C12	0.0117 (2)	0.24610 (7)	−0.09082 (16)	0.0455 (4)
H12	−0.0537	0.2448	−0.1545	0.055*
C13	0.0137 (3)	0.28541 (7)	−0.02830 (18)	0.0519 (5)
H13	−0.0537	0.3109	−0.0494	0.062*
C14	0.1123 (3)	0.28797 (7)	0.06395 (18)	0.0530 (5)
H14	0.1141	0.3153	0.1036	0.064*
C15	0.2100 (3)	0.24996 (6)	0.09897 (16)	0.0454 (4)
H15	0.2778	0.2516	0.1616	0.054*
C16	0.2047 (2)	0.20999 (5)	0.03956 (13)	0.0342 (3)
C17	0.21755 (19)	0.13252 (5)	0.15373 (12)	0.0298 (3)
C18	0.0724 (2)	0.09876 (6)	0.11544 (14)	0.0358 (4)
H18A	−0.0209	0.1169	0.0820	0.043*
H18B	0.1227	0.0793	0.0598	0.043*
C19	−0.0128 (2)	0.06708 (6)	0.19792 (15)	0.0387 (4)
C20	−0.0855 (3)	0.02613 (7)	0.1602 (2)	0.0550 (5)
H20	−0.0829	0.0197	0.0869	0.066*
C21	−0.1623 (3)	−0.00549 (8)	0.2298 (3)	0.0697 (7)
H21	−0.2107	−0.0328	0.2028	0.084*
C22	−0.1672 (3)	0.00321 (9)	0.3375 (2)	0.0694 (7)
H22	−0.2169	−0.0183	0.3842	0.083*
C23	−0.0990 (3)	0.04354 (9)	0.3761 (2)	0.0653 (6)
H23	−0.1033	0.0498	0.4494	0.078*
C24	−0.0228 (3)	0.07536 (7)	0.30671 (17)	0.0517 (5)
H24	0.0225	0.1029	0.3344	0.062*
C25	0.1402 (2)	0.16665 (6)	0.23502 (13)	0.0357 (4)
C26	−0.1178 (4)	0.20778 (9)	0.2834 (2)	0.0752 (7)
H26A	−0.1124	0.1962	0.3558	0.113*
H26B	−0.2392	0.2110	0.2614	0.113*
H26C	−0.0605	0.2374	0.2802	0.113*
C27	0.5916 (3)	0.18816 (9)	0.0023 (2)	0.0626 (6)
H27A	0.7088	0.1930	0.0305	0.094*
H27B	0.5430	0.2172	−0.0214	0.094*
H27C	0.5966	0.1671	−0.0574	0.094*
C28	0.0617 (3)	0.15200 (8)	−0.21054 (15)	0.0505 (5)
H28A	−0.0588	0.1634	−0.2150	0.061*
H28B	0.0571	0.1184	−0.2136	0.061*
C29	0.1629 (3)	0.16950 (10)	−0.30642 (18)	0.0690 (7)
H29A	0.1616	0.2031	−0.3065	0.083*
H29B	0.2852	0.1595	−0.3007	0.083*
C30	0.0850 (4)	0.15207 (12)	−0.41017 (19)	0.0840 (8)
H30A	0.0914	0.1188	−0.4118	0.126*
H30B	0.1501	0.1646	−0.4695	0.126*
H30C	−0.0365	0.1616	−0.4156	0.126*
N1	0.48008 (18)	0.16871 (5)	0.08585 (13)	0.0412 (3)
N2	0.1382 (2)	0.16591 (5)	−0.10730 (11)	0.0412 (3)
O1	0.3160 (2)	0.10260 (5)	−0.08116 (11)	0.0526 (3)
O2	0.21833 (19)	0.18395 (5)	0.30852 (11)	0.0523 (3)
O3	−0.02944 (16)	0.17580 (4)	0.21260 (10)	0.0455 (3)
Cl1	0.39756 (9)	0.07585 (2)	0.43710 (4)	0.06494 (18)
Cl2	0.36248 (10)	−0.09601 (2)	0.28361 (7)	0.0864 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0429 (9)	0.0406 (9)	0.0438 (10)	0.0073 (7)	0.0002 (7)	0.0091 (8)
C2	0.0486 (11)	0.0475 (11)	0.0574 (12)	0.0055 (8)	0.0043 (9)	0.0206 (9)
C3	0.0426 (10)	0.0336 (9)	0.0799 (15)	0.0030 (7)	0.0064 (9)	0.0123 (9)
C4	0.0512 (11)	0.0383 (10)	0.0631 (13)	0.0060 (8)	0.0058 (9)	−0.0036 (9)
C5	0.0458 (10)	0.0399 (10)	0.0467 (10)	0.0081 (8)	0.0065 (8)	0.0042 (8)
C6	0.0334 (8)	0.0331 (8)	0.0419 (9)	0.0061 (6)	0.0006 (7)	0.0072 (7)
C7	0.0353 (8)	0.0329 (8)	0.0363 (9)	0.0024 (6)	−0.0057 (6)	0.0058 (6)
C8	0.0335 (9)	0.0448 (10)	0.0586 (12)	0.0027 (7)	−0.0015 (8)	0.0143 (8)
C9	0.0354 (8)	0.0310 (8)	0.0324 (8)	0.0005 (6)	−0.0035 (6)	0.0026 (6)
C10	0.0463 (9)	0.0366 (9)	0.0328 (9)	−0.0014 (7)	0.0035 (7)	0.0020 (7)
C11	0.0383 (8)	0.0363 (9)	0.0328 (8)	−0.0024 (7)	−0.0006 (6)	0.0044 (6)
C12	0.0428 (9)	0.0507 (11)	0.0429 (10)	0.0034 (8)	−0.0064 (8)	0.0115 (8)
C13	0.0530 (11)	0.0409 (10)	0.0617 (13)	0.0120 (8)	−0.0024 (9)	0.0129 (9)
C14	0.0661 (13)	0.0320 (9)	0.0607 (13)	0.0036 (9)	−0.0033 (10)	−0.0016 (8)
C15	0.0566 (11)	0.0331 (9)	0.0462 (10)	−0.0008 (8)	−0.0112 (8)	0.0003 (7)
C16	0.0383 (8)	0.0300 (8)	0.0344 (8)	−0.0008 (6)	−0.0033 (6)	0.0054 (6)
C17	0.0314 (7)	0.0287 (7)	0.0292 (8)	0.0016 (6)	−0.0038 (6)	0.0016 (6)
C18	0.0356 (8)	0.0346 (8)	0.0373 (9)	−0.0021 (6)	−0.0042 (7)	−0.0016 (7)
C19	0.0296 (8)	0.0363 (9)	0.0500 (10)	0.0000 (6)	−0.0019 (7)	0.0034 (7)
C20	0.0485 (11)	0.0447 (11)	0.0719 (14)	−0.0079 (8)	0.0065 (10)	−0.0063 (10)
C21	0.0538 (12)	0.0422 (12)	0.113 (2)	−0.0126 (9)	0.0122 (13)	0.0043 (13)
C22	0.0523 (12)	0.0620 (14)	0.094 (2)	−0.0061 (11)	0.0183 (12)	0.0274 (13)
C23	0.0617 (13)	0.0741 (16)	0.0603 (14)	−0.0106 (11)	0.0110 (11)	0.0193 (12)
C24	0.0517 (11)	0.0534 (12)	0.0499 (12)	−0.0129 (9)	0.0014 (9)	0.0072 (9)
C25	0.0415 (9)	0.0326 (8)	0.0329 (8)	0.0021 (7)	−0.0021 (7)	0.0020 (6)
C26	0.0779 (16)	0.0790 (17)	0.0689 (16)	0.0340 (13)	0.0173 (12)	−0.0145 (13)
C27	0.0469 (11)	0.0669 (14)	0.0742 (15)	−0.0074 (10)	0.0080 (10)	0.0274 (12)
C28	0.0590 (11)	0.0574 (12)	0.0349 (10)	−0.0063 (9)	−0.0075 (8)	−0.0045 (8)
C29	0.0680 (14)	0.101 (2)	0.0381 (11)	−0.0087 (13)	0.0017 (10)	0.0019 (11)
C30	0.0926 (19)	0.124 (3)	0.0351 (12)	0.0123 (17)	0.0002 (12)	−0.0111 (13)
N1	0.0341 (7)	0.0395 (8)	0.0498 (9)	−0.0018 (6)	−0.0025 (6)	0.0130 (6)
N2	0.0517 (8)	0.0428 (8)	0.0289 (7)	0.0006 (7)	−0.0058 (6)	−0.0009 (6)
O1	0.0706 (9)	0.0416 (7)	0.0459 (8)	0.0095 (6)	0.0077 (6)	−0.0063 (6)
O2	0.0649 (8)	0.0495 (8)	0.0424 (8)	0.0023 (6)	−0.0125 (6)	−0.0131 (6)
O3	0.0418 (7)	0.0473 (7)	0.0473 (7)	0.0131 (5)	0.0022 (5)	−0.0050 (6)
Cl1	0.0957 (4)	0.0589 (3)	0.0401 (3)	0.0111 (3)	−0.0062 (3)	0.0068 (2)
Cl2	0.0968 (5)	0.0375 (3)	0.1251 (6)	−0.0044 (3)	0.0081 (4)	0.0214 (3)

C1—C6	1.383 (2)	C17—C18	1.539 (2)
C1—C2	1.387 (3)	C18—C19	1.520 (2)
C1—Cl1	1.736 (2)	C18—H18A	0.9700
C2—C3	1.369 (3)	C18—H18B	0.9700
C2—H2	0.9300	C19—C24	1.376 (3)
C3—C4	1.373 (3)	C19—C20	1.384 (3)
C3—Cl2	1.7356 (19)	C20—C21	1.388 (3)
C4—C5	1.384 (3)	C20—H20	0.9300
C4—H4	0.9300	C21—C22	1.362 (4)
C5—C6	1.392 (3)	C21—H21	0.9300
C5—H5	0.9300	C22—C23	1.359 (4)
C6—C7	1.509 (2)	C22—H22	0.9300
C7—C8	1.527 (2)	C23—C24	1.388 (3)
C7—C17	1.577 (2)	C23—H23	0.9300
C7—H7	0.9800	C24—H24	0.9300
C8—N1	1.451 (2)	C25—O2	1.193 (2)
C8—H8A	0.9700	C25—O3	1.336 (2)
C8—H8B	0.9700	C26—O3	1.442 (2)
C9—N1	1.456 (2)	C26—H26A	0.9600
C9—C16	1.507 (2)	C26—H26B	0.9600
C9—C10	1.550 (2)	C26—H26C	0.9600
C9—C17	1.605 (2)	C27—N1	1.455 (2)
C10—O1	1.218 (2)	C27—H27A	0.9600
C10—N2	1.360 (2)	C27—H27B	0.9600
C11—C12	1.378 (2)	C27—H27C	0.9600
C11—C16	1.385 (2)	C28—N2	1.460 (2)
C11—N2	1.404 (2)	C28—C29	1.508 (3)
C12—C13	1.375 (3)	C28—H28A	0.9700
C12—H12	0.9300	C28—H28B	0.9700
C13—C14	1.364 (3)	C29—C30	1.500 (3)
C13—H13	0.9300	C29—H29A	0.9700
C14—C15	1.390 (3)	C29—H29B	0.9700
C14—H14	0.9300	C30—H30A	0.9600
C15—C16	1.370 (2)	C30—H30B	0.9600
C15—H15	0.9300	C30—H30C	0.9600
C17—C25	1.530 (2)
C6—C1—C2	122.61 (19)	C19—C18—H18A	107.7
C6—C1—Cl1	121.26 (14)	C17—C18—H18A	107.7
C2—C1—Cl1	116.14 (15)	C19—C18—H18B	107.7
C3—C2—C1	118.30 (18)	C17—C18—H18B	107.7
C3—C2—H2	120.9	H18A—C18—H18B	107.1
C1—C2—H2	120.9	C24—C19—C20	117.20 (18)
C2—C3—C4	121.67 (18)	C24—C19—C18	125.81 (16)
C2—C3—Cl2	118.71 (17)	C20—C19—C18	116.99 (17)
C4—C3—Cl2	119.60 (18)	C19—C20—C21	121.1 (2)
C3—C4—C5	118.64 (19)	C19—C20—H20	119.4
C3—C4—H4	120.7	C21—C20—H20	119.4
C5—C4—H4	120.7	C22—C21—C20	120.4 (2)
C4—C5—C6	122.10 (18)	C22—C21—H21	119.8
C4—C5—H5	118.9	C20—C21—H21	119.8
C6—C5—H5	118.9	C23—C22—C21	119.5 (2)
C1—C6—C5	116.61 (16)	C23—C22—H22	120.3
C1—C6—C7	121.66 (16)	C21—C22—H22	120.3
C5—C6—C7	121.72 (16)	C22—C23—C24	120.3 (2)
C6—C7—C8	112.70 (14)	C22—C23—H23	119.8
C6—C7—C17	116.98 (13)	C24—C23—H23	119.8
C8—C7—C17	105.37 (13)	C19—C24—C23	121.5 (2)
C6—C7—H7	107.1	C19—C24—H24	119.3
C8—C7—H7	107.1	C23—C24—H24	119.3
C17—C7—H7	107.1	O2—C25—O3	123.05 (16)
N1—C8—C7	103.09 (14)	O2—C25—C17	125.83 (15)
N1—C8—H8A	111.1	O3—C25—C17	111.11 (14)
C7—C8—H8A	111.1	O3—C26—H26A	109.5
N1—C8—H8B	111.1	O3—C26—H26B	109.5
C7—C8—H8B	111.1	H26A—C26—H26B	109.5
H8A—C8—H8B	109.1	O3—C26—H26C	109.5
N1—C9—C16	112.40 (13)	H26A—C26—H26C	109.5
N1—C9—C10	115.24 (14)	H26B—C26—H26C	109.5
C16—C9—C10	100.96 (13)	N1—C27—H27A	109.5
N1—C9—C17	103.19 (12)	N1—C27—H27B	109.5
C16—C9—C17	116.61 (13)	H27A—C27—H27B	109.5
C10—C9—C17	108.92 (12)	N1—C27—H27C	109.5
O1—C10—N2	125.15 (17)	H27A—C27—H27C	109.5
O1—C10—C9	126.75 (16)	H27B—C27—H27C	109.5
N2—C10—C9	108.09 (14)	N2—C28—C29	113.74 (17)
C12—C11—C16	121.37 (16)	N2—C28—H28A	108.8
C12—C11—N2	129.12 (16)	C29—C28—H28A	108.8
C16—C11—N2	109.46 (14)	N2—C28—H28B	108.8
C13—C12—C11	117.81 (18)	C29—C28—H28B	108.8
C13—C12—H12	121.1	H28A—C28—H28B	107.7
C11—C12—H12	121.1	C30—C29—C28	111.6 (2)
C14—C13—C12	121.56 (18)	C30—C29—H29A	109.3
C14—C13—H13	119.2	C28—C29—H29A	109.3
C12—C13—H13	119.2	C30—C29—H29B	109.3
C13—C14—C15	120.37 (18)	C28—C29—H29B	109.3
C13—C14—H14	119.8	H29A—C29—H29B	108.0
C15—C14—H14	119.8	C29—C30—H30A	109.5
C16—C15—C14	118.82 (18)	C29—C30—H30B	109.5
C16—C15—H15	120.6	H30A—C30—H30B	109.5
C14—C15—H15	120.6	C29—C30—H30C	109.5
C15—C16—C11	119.97 (15)	H30A—C30—H30C	109.5
C15—C16—C9	130.58 (16)	H30B—C30—H30C	109.5
C11—C16—C9	109.42 (14)	C8—N1—C27	114.20 (15)
C25—C17—C18	109.67 (13)	C8—N1—C9	107.01 (13)
C25—C17—C7	109.73 (13)	C27—N1—C9	115.56 (15)
C18—C17—C7	116.11 (13)	C10—N2—C11	111.17 (14)
C25—C17—C9	105.54 (12)	C10—N2—C28	123.42 (16)
C18—C17—C9	112.66 (13)	C11—N2—C28	125.32 (15)
C7—C17—C9	102.46 (11)	C25—O3—C26	116.54 (17)
C19—C18—C17	118.45 (14)
C6—C1—C2—C3	1.2 (3)	C16—C9—C17—C25	−28.00 (17)
Cl1—C1—C2—C3	−178.64 (15)	C10—C9—C17—C25	−141.37 (13)
C1—C2—C3—C4	1.1 (3)	N1—C9—C17—C18	−144.62 (13)
C1—C2—C3—Cl2	179.34 (14)	C16—C9—C17—C18	91.65 (16)
C2—C3—C4—C5	−1.5 (3)	C10—C9—C17—C18	−21.72 (17)
Cl2—C3—C4—C5	−179.75 (15)	N1—C9—C17—C7	−19.13 (15)
C3—C4—C5—C6	−0.3 (3)	C16—C9—C17—C7	−142.86 (14)
C2—C1—C6—C5	−2.9 (3)	C10—C9—C17—C7	103.78 (14)
Cl1—C1—C6—C5	176.96 (13)	C25—C17—C18—C19	−62.32 (18)
C2—C1—C6—C7	178.20 (16)	C7—C17—C18—C19	62.74 (19)
Cl1—C1—C6—C7	−2.0 (2)	C9—C17—C18—C19	−179.56 (13)
C4—C5—C6—C1	2.4 (3)	C17—C18—C19—C24	24.6 (3)
C4—C5—C6—C7	−178.66 (16)	C17—C18—C19—C20	−154.86 (16)
C1—C6—C7—C8	127.31 (18)	C24—C19—C20—C21	−1.1 (3)
C5—C6—C7—C8	−51.6 (2)	C18—C19—C20—C21	178.42 (18)
C1—C6—C7—C17	−110.32 (18)	C19—C20—C21—C22	−0.1 (4)
C5—C6—C7—C17	70.8 (2)	C20—C21—C22—C23	1.1 (4)
C6—C7—C8—N1	158.73 (15)	C21—C22—C23—C24	−0.8 (4)
C17—C7—C8—N1	30.04 (18)	C20—C19—C24—C23	1.4 (3)
N1—C9—C10—O1	50.1 (2)	C18—C19—C24—C23	−178.06 (18)
C16—C9—C10—O1	171.47 (17)	C22—C23—C24—C19	−0.5 (4)
C17—C9—C10—O1	−65.2 (2)	C18—C17—C25—O2	148.57 (17)
N1—C9—C10—N2	−130.73 (15)	C7—C17—C25—O2	19.9 (2)
C16—C9—C10—N2	−9.37 (17)	C9—C17—C25—O2	−89.82 (19)
C17—C9—C10—N2	113.91 (14)	C18—C17—C25—O3	−32.52 (18)
C16—C11—C12—C13	1.2 (3)	C7—C17—C25—O3	−161.18 (13)
N2—C11—C12—C13	−175.90 (17)	C9—C17—C25—O3	89.09 (15)
C11—C12—C13—C14	1.5 (3)	N2—C28—C29—C30	176.8 (2)
C12—C13—C14—C15	−1.9 (3)	C7—C8—N1—C27	−174.07 (17)
C13—C14—C15—C16	−0.3 (3)	C7—C8—N1—C9	−44.87 (18)
C14—C15—C16—C11	2.9 (3)	C16—C9—N1—C8	166.61 (15)
C14—C15—C16—C9	−179.25 (17)	C10—C9—N1—C8	−78.45 (18)
C12—C11—C16—C15	−3.5 (3)	C17—C9—N1—C8	40.15 (17)
N2—C11—C16—C15	174.18 (16)	C16—C9—N1—C27	−65.0 (2)
C12—C11—C16—C9	178.32 (15)	C10—C9—N1—C27	50.0 (2)
N2—C11—C16—C9	−4.06 (18)	C17—C9—N1—C27	168.57 (16)
N1—C9—C16—C15	−46.7 (2)	O1—C10—N2—C11	−173.11 (16)
C10—C9—C16—C15	−170.01 (18)	C9—C10—N2—C11	7.72 (19)
C17—C9—C16—C15	72.2 (2)	O1—C10—N2—C28	3.8 (3)
N1—C9—C16—C11	131.31 (15)	C9—C10—N2—C28	−175.39 (15)
C10—C9—C16—C11	7.97 (16)	C12—C11—N2—C10	174.91 (17)
C17—C9—C16—C11	−109.83 (16)	C16—C11—N2—C10	−2.48 (19)
C6—C7—C17—C25	115.66 (16)	C12—C11—N2—C28	−1.9 (3)
C8—C7—C17—C25	−118.25 (15)	C16—C11—N2—C28	−179.30 (16)
C6—C7—C17—C18	−9.4 (2)	C29—C28—N2—C10	−93.2 (2)
C8—C7—C17—C18	116.72 (16)	C29—C28—N2—C11	83.2 (2)
C6—C7—C17—C9	−132.57 (14)	O2—C25—O3—C26	−0.9 (3)
C8—C7—C17—C9	−6.48 (17)	C17—C25—O3—C26	−179.80 (17)
N1—C9—C17—C25	95.73 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18B···O1	0.97	2.39	3.073 (2)	127
C13—H13···O2i	0.93	2.46	3.132 (2)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18B⋯O1	0.97	2.39	3.073 (2)	127
C13—H13⋯O2i	0.93	2.46	3.132 (2)	129

Symmetry code: (i) .