Methyl 4'-(3-bromo-phen-yl)-3'-(2,5-di-methyl-benz-yl)-1'-methyl-2-oxo-spiro-[indo-line-3,2'-pyrrolidine]-3'-carboxyl-ate.

In the title compound, C29H29BrN2O3, the indole ring system is essentially planar (r.m.s. deviation = 0.079 Å) and makes a dihedral angle of 85.23 (10)° with the mean plane of the 4-methyl-pyrrolidine ring. This ring adopts an envelope conformation with the N atom at the flap. The pyrrolidine 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. In the crystal, mol-ecules are linked via pairs of C-H⋯O hydrogen bonds, forming inversion dimers with an R 2 (2)(14) ring motif. These dimers are further linked by N-H⋯O and C-H⋯O hydrogen bonds, forming two-dimensional networks lying parallel to (10-1).

Related literature

For the biological activity of spiro-pyrrolidine derivatives, see: Obniska et al. (2002 ▶); Saito et al. (1991 ▶); Hilton et al. (2000 ▶). For related crystal structures, see: Jagadeesan et al. (2013 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For graph-set motif notations, see: Bernstein et al. (1995 ▶). For bond-length distortions in small rings, see: Allen (1981 ▶).

Experimental

Crystal data

C29H29BrN2O3

M = 533.45

Monoclinic,

a = 12.0673 (4) Å

b = 9.4109 (3) Å

c = 22.5852 (7) Å

β = 103.660 (2)°

V = 2492.32 (14) Å3

Z = 4

Mo Kα radiation

μ = 1.68 mm−1

T = 293 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker 2008 ▶) T min = 0.564, T max = 0.657

23085 measured reflections

4898 independent reflections

3487 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.097

S = 1.01

4898 reflections

320 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.37 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/S1600536814002967/su2698sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814002967/su2698Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814002967/su2698Isup3.cml

CCDC reference:

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

C29H29BrN2O3	F(000) = 1104
Mr = 533.45	Dx = 1.422 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2yn	Cell parameters from 4898 reflections
a = 12.0673 (4) Å	θ = 2.2–26.0°
b = 9.4109 (3) Å	µ = 1.68 mm−1
c = 22.5852 (7) Å	T = 293 K
β = 103.660 (2)°	Block, colorless
V = 2492.32 (14) Å3	0.35 × 0.30 × 0.25 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	4898 independent reflections
Radiation source: fine-focus sealed tube	3487 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker 2008)	h = −14→14
Tmin = 0.564, Tmax = 0.657	k = −11→11
23085 measured reflections	l = −27→23

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.049P)2 + 0.846P] where P = (Fo2 + 2Fc2)/3
4898 reflections	(Δ/σ)max = 0.001
320 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.37 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	0.19054 (18)	0.7464 (2)	0.45559 (9)	0.0337 (5)
H1	0.1890	0.8197	0.4830	0.040*
C2	0.29340 (19)	0.6963 (3)	0.44773 (10)	0.0406 (5)
C3	0.2988 (2)	0.5886 (3)	0.40750 (11)	0.0480 (6)
H3	0.3687	0.5564	0.4022	0.058*
C4	0.1991 (2)	0.5298 (3)	0.37549 (10)	0.0469 (6)
H4	0.2015	0.4563	0.3483	0.056*
C5	0.09473 (19)	0.5775 (2)	0.38276 (10)	0.0376 (5)
H5	0.0278	0.5356	0.3608	0.045*
C6	0.08958 (17)	0.6878 (2)	0.42272 (9)	0.0309 (5)
C7	−0.02180 (17)	0.7436 (2)	0.43366 (9)	0.0291 (5)
H7	−0.0019	0.8094	0.4682	0.035*
C8	−0.09576 (17)	0.6270 (2)	0.45184 (10)	0.0355 (5)
H8A	−0.0850	0.5375	0.4327	0.043*
H8B	−0.0772	0.6141	0.4957	0.043*
C9	−0.22078 (17)	0.7398 (2)	0.37089 (9)	0.0269 (4)
C10	−0.23087 (17)	0.6300 (2)	0.31808 (9)	0.0317 (5)
C11	−0.38171 (18)	0.7809 (2)	0.29012 (9)	0.0333 (5)
C12	−0.48250 (19)	0.8392 (3)	0.25872 (11)	0.0466 (6)
H12	−0.5152	0.8125	0.2188	0.056*
C13	−0.5336 (2)	0.9379 (3)	0.28800 (12)	0.0574 (7)
H13	−0.6017	0.9796	0.2674	0.069*
C14	−0.4859 (2)	0.9770 (3)	0.34747 (12)	0.0541 (7)
H14	−0.5230	1.0426	0.3668	0.065*
C15	−0.38347 (18)	0.9189 (2)	0.37835 (10)	0.0399 (5)
H15	−0.3514	0.9444	0.4185	0.048*
C16	−0.32970 (16)	0.8232 (2)	0.34905 (9)	0.0297 (5)
C17	−0.10458 (16)	0.8266 (2)	0.38018 (8)	0.0258 (4)
C18	−0.06611 (16)	0.8413 (2)	0.32054 (9)	0.0288 (4)
H18A	−0.0465	0.7473	0.3087	0.035*
H18B	−0.1310	0.8737	0.2894	0.035*
C19	0.03291 (16)	0.9389 (2)	0.31960 (9)	0.0300 (5)
C20	0.09418 (17)	1.0100 (2)	0.37079 (9)	0.0337 (5)
H20	0.0720	0.9991	0.4072	0.040*
C21	0.18680 (17)	1.0964 (2)	0.37017 (10)	0.0388 (5)
C22	0.21530 (19)	1.1154 (3)	0.31553 (12)	0.0463 (6)
H22	0.2756	1.1751	0.3134	0.056*
C23	0.15609 (19)	1.0475 (3)	0.26388 (11)	0.0476 (6)
H23	0.1772	1.0626	0.2274	0.057*
C24	0.06569 (18)	0.9570 (2)	0.26467 (10)	0.0373 (5)
C25	−0.13018 (16)	0.9724 (2)	0.40407 (9)	0.0283 (4)
C26	−0.1905 (3)	1.2069 (2)	0.37822 (12)	0.0588 (8)
H26A	−0.2565	1.2010	0.3949	0.088*
H26B	−0.2058	1.2699	0.3438	0.088*
H26C	−0.1272	1.2426	0.4087	0.088*
C27	−0.2983 (2)	0.5739 (3)	0.43525 (11)	0.0453 (6)
H27A	−0.3725	0.6139	0.4191	0.068*
H27B	−0.2906	0.5493	0.4773	0.068*
H27C	−0.2892	0.4902	0.4126	0.068*
C28	0.2541 (2)	1.1619 (3)	0.42803 (12)	0.0599 (7)
H28A	0.2029	1.1957	0.4516	0.090*
H28B	0.2980	1.2400	0.4185	0.090*
H28C	0.3044	1.0921	0.4510	0.090*
C29	0.0049 (2)	0.8811 (3)	0.20775 (11)	0.0535 (7)
H29A	0.0399	0.9050	0.1750	0.080*
H29B	−0.0737	0.9095	0.1972	0.080*
H29C	0.0098	0.7804	0.2146	0.080*
N1	−0.21158 (14)	0.67732 (18)	0.43036 (7)	0.0313 (4)
N2	−0.31885 (15)	0.67136 (19)	0.27236 (8)	0.0379 (4)
H2	−0.3343	0.6344	0.2365	0.045*
O1	−0.17294 (13)	0.52493 (16)	0.31804 (7)	0.0436 (4)
O2	−0.12565 (12)	0.99948 (15)	0.45631 (6)	0.0369 (4)
O3	−0.16324 (12)	1.06736 (14)	0.35912 (6)	0.0355 (3)
Br1	0.43004 (2)	0.77598 (4)	0.494958 (15)	0.07456 (14)

	U11	U22	U33	U12	U13	U23
C1	0.0376 (11)	0.0362 (12)	0.0262 (11)	0.0051 (9)	0.0051 (9)	−0.0006 (9)
C2	0.0361 (11)	0.0516 (15)	0.0331 (12)	0.0029 (10)	0.0063 (10)	0.0019 (11)
C3	0.0414 (13)	0.0620 (17)	0.0441 (14)	0.0161 (11)	0.0170 (11)	−0.0023 (12)
C4	0.0540 (14)	0.0501 (15)	0.0366 (13)	0.0154 (12)	0.0109 (11)	−0.0081 (11)
C5	0.0406 (12)	0.0369 (13)	0.0325 (12)	0.0075 (10)	0.0030 (9)	−0.0042 (10)
C6	0.0358 (11)	0.0312 (12)	0.0245 (11)	0.0081 (9)	0.0050 (9)	0.0050 (9)
C7	0.0332 (10)	0.0304 (12)	0.0222 (10)	0.0068 (8)	0.0033 (8)	−0.0008 (8)
C8	0.0415 (12)	0.0361 (12)	0.0278 (11)	0.0097 (10)	0.0059 (9)	0.0098 (9)
C9	0.0327 (10)	0.0252 (11)	0.0225 (10)	0.0022 (8)	0.0058 (8)	−0.0001 (8)
C10	0.0385 (11)	0.0259 (11)	0.0317 (11)	−0.0047 (9)	0.0102 (9)	0.0002 (9)
C11	0.0373 (11)	0.0323 (12)	0.0290 (11)	−0.0044 (9)	0.0050 (9)	0.0034 (9)
C12	0.0398 (12)	0.0566 (16)	0.0360 (13)	−0.0027 (11)	−0.0060 (10)	0.0053 (12)
C13	0.0387 (13)	0.0726 (19)	0.0536 (17)	0.0163 (13)	−0.0033 (12)	0.0064 (14)
C14	0.0442 (13)	0.0628 (17)	0.0547 (16)	0.0201 (12)	0.0105 (12)	−0.0009 (13)
C15	0.0373 (11)	0.0454 (14)	0.0359 (12)	0.0070 (10)	0.0068 (10)	−0.0032 (11)
C16	0.0306 (10)	0.0305 (11)	0.0273 (11)	−0.0007 (9)	0.0052 (8)	0.0027 (9)
C17	0.0309 (10)	0.0249 (10)	0.0202 (10)	0.0025 (8)	0.0032 (8)	−0.0009 (8)
C18	0.0346 (10)	0.0287 (11)	0.0228 (10)	0.0019 (9)	0.0064 (8)	−0.0005 (8)
C19	0.0318 (10)	0.0288 (11)	0.0292 (11)	0.0054 (9)	0.0068 (9)	0.0048 (9)
C20	0.0358 (11)	0.0343 (12)	0.0303 (11)	0.0025 (9)	0.0066 (9)	0.0027 (10)
C21	0.0315 (11)	0.0390 (13)	0.0438 (13)	0.0021 (9)	0.0049 (10)	0.0065 (11)
C22	0.0309 (11)	0.0473 (15)	0.0623 (16)	−0.0012 (10)	0.0142 (11)	0.0078 (13)
C23	0.0432 (13)	0.0630 (17)	0.0424 (14)	0.0029 (12)	0.0220 (11)	0.0072 (12)
C24	0.0365 (11)	0.0448 (13)	0.0323 (12)	0.0083 (10)	0.0114 (9)	0.0018 (10)
C25	0.0286 (10)	0.0273 (11)	0.0278 (12)	0.0012 (8)	0.0043 (8)	0.0003 (9)
C26	0.097 (2)	0.0291 (14)	0.0526 (16)	0.0220 (14)	0.0221 (15)	0.0055 (12)
C27	0.0494 (13)	0.0448 (14)	0.0441 (14)	−0.0038 (11)	0.0158 (11)	0.0099 (11)
C28	0.0589 (16)	0.0549 (17)	0.0590 (17)	−0.0165 (13)	0.0001 (13)	−0.0031 (13)
C29	0.0605 (15)	0.0702 (19)	0.0335 (13)	0.0021 (14)	0.0187 (12)	−0.0041 (12)
N1	0.0363 (9)	0.0324 (10)	0.0255 (9)	0.0027 (8)	0.0082 (7)	0.0065 (7)
N2	0.0466 (10)	0.0388 (11)	0.0244 (9)	−0.0049 (9)	0.0009 (8)	−0.0063 (8)
O1	0.0519 (9)	0.0305 (9)	0.0476 (10)	0.0035 (7)	0.0101 (8)	−0.0076 (7)
O2	0.0509 (9)	0.0340 (8)	0.0241 (8)	0.0075 (7)	0.0058 (6)	−0.0052 (6)
O3	0.0515 (9)	0.0246 (8)	0.0305 (8)	0.0110 (7)	0.0098 (7)	0.0047 (6)
Br1	0.03672 (15)	0.1020 (3)	0.0809 (2)	−0.00654 (14)	0.00577 (14)	−0.02329 (18)

C1—C2	1.378 (3)	C15—H15	0.9300
C1—C6	1.383 (3)	C17—C18	1.531 (3)
C1—H1	0.9300	C17—C25	1.532 (3)
C2—C3	1.373 (3)	C18—C19	1.511 (3)
C2—Br1	1.895 (2)	C18—H18A	0.9700
C3—C4	1.366 (3)	C18—H18B	0.9700
C3—H3	0.9300	C19—C20	1.388 (3)
C4—C5	1.383 (3)	C19—C24	1.399 (3)
C4—H4	0.9300	C20—C21	1.385 (3)
C5—C6	1.386 (3)	C20—H20	0.9300
C5—H5	0.9300	C21—C22	1.369 (3)
C6—C7	1.517 (3)	C21—C28	1.499 (3)
C7—C8	1.531 (3)	C22—C23	1.373 (3)
C7—C17	1.580 (3)	C22—H22	0.9300
C7—H7	0.9800	C23—C24	1.387 (3)
C8—N1	1.447 (3)	C23—H23	0.9300
C8—H8A	0.9700	C24—C29	1.502 (3)
C8—H8B	0.9700	C25—O2	1.196 (2)
C9—N1	1.446 (2)	C25—O3	1.341 (2)
C9—C16	1.510 (3)	C26—O3	1.444 (3)
C9—C10	1.561 (3)	C26—H26A	0.9600
C9—C17	1.593 (3)	C26—H26B	0.9600
C10—O1	1.211 (2)	C26—H26C	0.9600
C10—N2	1.352 (3)	C27—N1	1.452 (3)
C11—C12	1.370 (3)	C27—H27A	0.9600
C11—C16	1.389 (3)	C27—H27B	0.9600
C11—N2	1.394 (3)	C27—H27C	0.9600
C12—C13	1.369 (4)	C28—H28A	0.9600
C12—H12	0.9300	C28—H28B	0.9600
C13—C14	1.380 (4)	C28—H28C	0.9600
C13—H13	0.9300	C29—H29A	0.9600
C14—C15	1.381 (3)	C29—H29B	0.9600
C14—H14	0.9300	C29—H29C	0.9600
C15—C16	1.368 (3)	N2—H2	0.8600
C2—C1—C6	120.0 (2)	C25—C17—C9	105.13 (15)
C2—C1—H1	120.0	C7—C17—C9	103.01 (15)
C6—C1—H1	120.0	C19—C18—C17	118.18 (16)
C3—C2—C1	121.5 (2)	C19—C18—H18A	107.8
C3—C2—Br1	119.58 (17)	C17—C18—H18A	107.8
C1—C2—Br1	118.86 (17)	C19—C18—H18B	107.8
C4—C3—C2	118.4 (2)	C17—C18—H18B	107.8
C4—C3—H3	120.8	H18A—C18—H18B	107.1
C2—C3—H3	120.8	C20—C19—C24	118.23 (19)
C3—C4—C5	121.2 (2)	C20—C19—C18	123.28 (18)
C3—C4—H4	119.4	C24—C19—C18	118.48 (18)
C5—C4—H4	119.4	C21—C20—C19	123.2 (2)
C4—C5—C6	120.2 (2)	C21—C20—H20	118.4
C4—C5—H5	119.9	C19—C20—H20	118.4
C6—C5—H5	119.9	C22—C21—C20	117.5 (2)
C1—C6—C5	118.60 (19)	C22—C21—C28	122.2 (2)
C1—C6—C7	118.46 (18)	C20—C21—C28	120.3 (2)
C5—C6—C7	122.91 (19)	C21—C22—C23	120.9 (2)
C6—C7—C8	112.97 (17)	C21—C22—H22	119.5
C6—C7—C17	118.13 (16)	C23—C22—H22	119.5
C8—C7—C17	104.84 (16)	C22—C23—C24	121.8 (2)
C6—C7—H7	106.8	C22—C23—H23	119.1
C8—C7—H7	106.8	C24—C23—H23	119.1
C17—C7—H7	106.8	C23—C24—C19	118.3 (2)
N1—C8—C7	104.69 (16)	C23—C24—C29	120.5 (2)
N1—C8—H8A	110.8	C19—C24—C29	121.2 (2)
C7—C8—H8A	110.8	O2—C25—O3	122.75 (18)
N1—C8—H8B	110.8	O2—C25—C17	124.94 (18)
C7—C8—H8B	110.8	O3—C25—C17	112.27 (16)
H8A—C8—H8B	108.9	O3—C26—H26A	109.5
N1—C9—C16	112.63 (16)	O3—C26—H26B	109.5
N1—C9—C10	114.52 (16)	H26A—C26—H26B	109.5
C16—C9—C10	100.93 (15)	O3—C26—H26C	109.5
N1—C9—C17	102.36 (15)	H26A—C26—H26C	109.5
C16—C9—C17	116.60 (16)	H26B—C26—H26C	109.5
C10—C9—C17	110.34 (15)	N1—C27—H27A	109.5
O1—C10—N2	125.7 (2)	N1—C27—H27B	109.5
O1—C10—C9	126.89 (18)	H27A—C27—H27B	109.5
N2—C10—C9	107.35 (17)	N1—C27—H27C	109.5
C12—C11—C16	121.8 (2)	H27A—C27—H27C	109.5
C12—C11—N2	128.6 (2)	H27B—C27—H27C	109.5
C16—C11—N2	109.52 (18)	C21—C28—H28A	109.5
C13—C12—C11	117.9 (2)	C21—C28—H28B	109.5
C13—C12—H12	121.1	H28A—C28—H28B	109.5
C11—C12—H12	121.1	C21—C28—H28C	109.5
C12—C13—C14	121.3 (2)	H28A—C28—H28C	109.5
C12—C13—H13	119.4	H28B—C28—H28C	109.5
C14—C13—H13	119.4	C24—C29—H29A	109.5
C13—C14—C15	120.2 (2)	C24—C29—H29B	109.5
C13—C14—H14	119.9	H29A—C29—H29B	109.5
C15—C14—H14	119.9	C24—C29—H29C	109.5
C16—C15—C14	119.1 (2)	H29A—C29—H29C	109.5
C16—C15—H15	120.4	H29B—C29—H29C	109.5
C14—C15—H15	120.4	C8—N1—C9	107.51 (16)
C15—C16—C11	119.56 (19)	C8—N1—C27	114.32 (17)
C15—C16—C9	131.25 (18)	C9—N1—C27	116.39 (16)
C11—C16—C9	109.01 (18)	C10—N2—C11	112.08 (17)
C18—C17—C25	110.94 (16)	C10—N2—H2	124.0
C18—C17—C7	116.66 (16)	C11—N2—H2	124.0
C25—C17—C7	108.48 (15)	C25—O3—C26	115.35 (17)
C18—C17—C9	111.76 (15)
C6—C1—C2—C3	0.2 (3)	C16—C9—C17—C18	−84.5 (2)
C6—C1—C2—Br1	−178.49 (16)	C10—C9—C17—C18	29.8 (2)
C1—C2—C3—C4	−0.8 (4)	N1—C9—C17—C25	−87.50 (17)
Br1—C2—C3—C4	177.86 (19)	C16—C9—C17—C25	35.9 (2)
C2—C3—C4—C5	0.5 (4)	C10—C9—C17—C25	150.20 (16)
C3—C4—C5—C6	0.5 (4)	N1—C9—C17—C7	26.04 (18)
C2—C1—C6—C5	0.8 (3)	C16—C9—C17—C7	149.43 (17)
C2—C1—C6—C7	178.69 (19)	C10—C9—C17—C7	−96.25 (17)
C4—C5—C6—C1	−1.1 (3)	C25—C17—C18—C19	54.2 (2)
C4—C5—C6—C7	−179.0 (2)	C7—C17—C18—C19	−70.7 (2)
C1—C6—C7—C8	−123.9 (2)	C9—C17—C18—C19	171.14 (16)
C5—C6—C7—C8	53.9 (3)	C17—C18—C19—C20	3.4 (3)
C1—C6—C7—C17	113.3 (2)	C17—C18—C19—C24	−177.57 (18)
C5—C6—C7—C17	−68.9 (3)	C24—C19—C20—C21	−0.8 (3)
C6—C7—C8—N1	−151.54 (17)	C18—C19—C20—C21	178.23 (19)
C17—C7—C8—N1	−21.6 (2)	C19—C20—C21—C22	2.5 (3)
N1—C9—C10—O1	−46.8 (3)	C19—C20—C21—C28	−175.7 (2)
C16—C9—C10—O1	−168.0 (2)	C20—C21—C22—C23	−1.9 (3)
C17—C9—C10—O1	68.0 (3)	C28—C21—C22—C23	176.2 (2)
N1—C9—C10—N2	131.64 (18)	C21—C22—C23—C24	−0.2 (4)
C16—C9—C10—N2	10.4 (2)	C22—C23—C24—C19	1.9 (3)
C17—C9—C10—N2	−113.53 (18)	C22—C23—C24—C29	−178.2 (2)
C16—C11—C12—C13	−2.3 (4)	C20—C19—C24—C23	−1.4 (3)
N2—C11—C12—C13	174.2 (2)	C18—C19—C24—C23	179.52 (19)
C11—C12—C13—C14	−0.6 (4)	C20—C19—C24—C29	178.7 (2)
C12—C13—C14—C15	1.5 (4)	C18—C19—C24—C29	−0.4 (3)
C13—C14—C15—C16	0.5 (4)	C18—C17—C25—O2	−154.57 (19)
C14—C15—C16—C11	−3.3 (3)	C7—C17—C25—O2	−25.2 (3)
C14—C15—C16—C9	−177.9 (2)	C9—C17—C25—O2	84.5 (2)
C12—C11—C16—C15	4.3 (3)	C18—C17—C25—O3	27.9 (2)
N2—C11—C16—C15	−172.80 (19)	C7—C17—C25—O3	157.27 (16)
C12—C11—C16—C9	−180.0 (2)	C9—C17—C25—O3	−93.08 (18)
N2—C11—C16—C9	2.9 (2)	C7—C8—N1—C9	41.1 (2)
N1—C9—C16—C15	44.6 (3)	C7—C8—N1—C27	171.93 (17)
C10—C9—C16—C15	167.2 (2)	C16—C9—N1—C8	−168.11 (17)
C17—C9—C16—C15	−73.3 (3)	C10—C9—N1—C8	77.3 (2)
N1—C9—C16—C11	−130.45 (18)	C17—C9—N1—C8	−42.09 (19)
C10—C9—C16—C11	−7.9 (2)	C16—C9—N1—C27	62.2 (2)
C17—C9—C16—C11	111.63 (19)	C10—C9—N1—C27	−52.4 (2)
C6—C7—C17—C18	1.2 (3)	C17—C9—N1—C27	−171.78 (17)
C8—C7—C17—C18	−125.60 (18)	O1—C10—N2—C11	168.9 (2)
C6—C7—C17—C25	−124.90 (19)	C9—C10—N2—C11	−9.6 (2)
C8—C7—C17—C25	108.28 (18)	C12—C11—N2—C10	−172.4 (2)
C6—C7—C17—C9	124.02 (18)	C16—C11—N2—C10	4.5 (3)
C8—C7—C17—C9	−2.80 (19)	O2—C25—O3—C26	1.5 (3)
N1—C9—C17—C18	152.06 (16)	C17—C25—O3—C26	179.14 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1	0.93	2.39	3.253 (3)	155
N2—H2···O3i	0.86	2.24	3.085 (2)	166
C1—H1···O2ii	0.93	2.42	3.321 (2)	163
C26—H26B···O1iii	0.96	2.52	3.315 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1	0.93	2.39	3.253 (3)	155
N2—H2⋯O3i	0.86	2.24	3.085 (2)	166
C1—H1⋯O2ii	0.93	2.42	3.321 (2)	163
C26—H26B⋯O1iii	0.96	2.52	3.315 (3)	140

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