tert-Butyl 3-benzyl-3-[(E)-2-benzyl-idene-3-oxocyclo-pent-yl]-2-oxoindoline-1-carboxyl-ate.

In the title compound, C(32)H(31)NO(4), the dihedral angles between the indoline ring and the two phenyl rings are 48.11 (9) and 66.55 (9)°. The mol-ecular conformation is stabilized by a weak intramolecular π-π stacking inter-action [centroid-centroid distance = 3.6377 (7) Å]. The crystal structure is stabilized by inter-molecular C-H⋯O hydrogen bonds, which form chains along the b axis.

Related literature

For the preparation of chiral 3,3-disubstituted 2-oxindoles, see: Cozzi et al. (2009 ▶); Qiao et al. (2010 ▶); Zhou et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C32H31NO4

M = 493.58

Orthorhombic,

a = 7.8695 (16) Å

b = 11.893 (2) Å

c = 28.346 (6) Å

V = 2652.9 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 173 K

0.35 × 0.26 × 0.12 mm

Data collection

Rigaku Saturn724+ diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ▶) T min = 0.525, T max = 1.000

9151 measured reflections

2967 independent reflections

2651 reflections with I > 2σ(I)

R int = 0.088

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.132

S = 1.05

2967 reflections

334 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELTXL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681100691X/rz2560sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681100691X/rz2560Isup2.hkl

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

C32H31NO4	F(000) = 1048
Mr = 493.58	Dx = 1.236 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7550 reflections
a = 7.8695 (16) Å	θ = 1.4–26.0°
b = 11.893 (2) Å	µ = 0.08 mm−1
c = 28.346 (6) Å	T = 173 K
V = 2652.9 (9) Å3	Block, colorless
Z = 4	0.35 × 0.26 × 0.12 mm

Rigaku Saturn724+ diffractometer	2967 independent reflections
Radiation source: Rotating Anode	2651 reflections with I > 2σ(I)
Confocal	Rint = 0.088
Detector resolution: 28.5714 pixels mm-1	θmax = 26.0°, θmin = 1.9°
ω scans at fixed χ = 45°	h = −9→6
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	k = −14→14
Tmin = 0.525, Tmax = 1.000	l = −18→34
9151 measured reflections

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0628P)2 + 0.4619P] where P = (Fo2 + 2Fc2)/3
2967 reflections	(Δ/σ)max < 0.001
334 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.23 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
O1	0.1446 (3)	0.51425 (19)	0.50716 (6)	0.0331 (5)
O2	0.1567 (4)	0.6816 (2)	0.46945 (7)	0.0458 (7)
O3	0.1853 (3)	0.66366 (19)	0.37455 (7)	0.0341 (5)
O4	−0.0170 (4)	0.7532 (2)	0.26192 (8)	0.0484 (7)
N1	0.1590 (3)	0.5157 (2)	0.42829 (7)	0.0247 (5)
C1	0.2941 (6)	0.6257 (4)	0.56693 (13)	0.0553 (11)
H1A	0.3020	0.6934	0.5474	0.083*
H1B	0.3916	0.5767	0.5605	0.083*
H1C	0.2941	0.6471	0.6003	0.083*
C2	−0.0256 (6)	0.6350 (4)	0.55892 (11)	0.0488 (10)
H2A	−0.0119	0.7023	0.5393	0.073*
H2B	−0.0437	0.6574	0.5918	0.073*
H2C	−0.1238	0.5918	0.5478	0.073*
C3	0.1162 (7)	0.4580 (3)	0.58547 (10)	0.0559 (12)
H3A	0.0102	0.4189	0.5776	0.084*
H3B	0.1154	0.4786	0.6189	0.084*
H3C	0.2129	0.4083	0.5791	0.084*
C4	0.1317 (5)	0.5638 (3)	0.55551 (9)	0.0381 (9)
C5	0.1538 (4)	0.5817 (3)	0.46984 (9)	0.0302 (7)
C6	0.1527 (4)	0.3956 (3)	0.42408 (9)	0.0248 (6)
C7	0.1196 (4)	0.3132 (3)	0.45733 (9)	0.0316 (7)
H7A	0.1044	0.3320	0.4896	0.038*
C8	0.1092 (5)	0.2022 (3)	0.44210 (10)	0.0335 (8)
H8A	0.0869	0.1449	0.4646	0.040*
C9	0.1304 (5)	0.1729 (3)	0.39534 (10)	0.0368 (8)
H9A	0.1213	0.0965	0.3858	0.044*
C10	0.1651 (5)	0.2567 (3)	0.36226 (9)	0.0291 (7)
H10A	0.1804	0.2379	0.3300	0.035*
C11	0.1771 (4)	0.3667 (3)	0.37675 (9)	0.0252 (6)
C12	0.2152 (4)	0.4694 (3)	0.34814 (9)	0.0241 (6)
C13	0.1835 (4)	0.5643 (3)	0.38325 (9)	0.0250 (6)
C14	0.4084 (4)	0.4752 (3)	0.33532 (9)	0.0262 (6)
H14A	0.4353	0.4136	0.3131	0.031*
H14B	0.4312	0.5472	0.3190	0.031*
C15	0.5246 (4)	0.4662 (3)	0.37767 (9)	0.0270 (6)
C16	0.5679 (5)	0.5611 (3)	0.40327 (11)	0.0352 (8)
H16A	0.5254	0.6324	0.3939	0.042*
C17	0.6733 (5)	0.5529 (3)	0.44273 (11)	0.0384 (8)
H17A	0.7012	0.6183	0.4603	0.046*
C18	0.7361 (5)	0.4508 (3)	0.45593 (11)	0.0376 (8)
H18A	0.8081	0.4454	0.4827	0.045*
C19	0.6955 (5)	0.3543 (3)	0.43046 (11)	0.0370 (8)
H19A	0.7404	0.2834	0.4395	0.044*
C20	0.5884 (4)	0.3630 (3)	0.39157 (10)	0.0303 (7)
H20A	0.5588	0.2973	0.3744	0.036*
C21	0.1013 (4)	0.4759 (3)	0.30321 (8)	0.0249 (6)
H21A	0.1178	0.4061	0.2841	0.030*
C22	−0.0884 (4)	0.4869 (3)	0.31628 (11)	0.0350 (8)
H22A	−0.1590	0.4424	0.2942	0.042*
H22B	−0.1081	0.4587	0.3487	0.042*
C23	−0.1352 (4)	0.6112 (3)	0.31313 (11)	0.0365 (8)
H23A	−0.2516	0.6207	0.3005	0.044*
H23B	−0.1289	0.6473	0.3446	0.044*
C24	−0.0066 (4)	0.6608 (3)	0.28029 (9)	0.0332 (7)
C25	0.1313 (4)	0.5785 (3)	0.27179 (9)	0.0247 (6)
C26	0.2475 (4)	0.5990 (3)	0.23824 (9)	0.0292 (7)
H26A	0.2390	0.6701	0.2231	0.035*
C27	0.3871 (4)	0.5258 (3)	0.22173 (9)	0.0272 (7)
C28	0.3654 (5)	0.4114 (3)	0.21275 (9)	0.0341 (8)
H28A	0.2567	0.3780	0.2167	0.041*
C29	0.5013 (5)	0.3463 (3)	0.19813 (10)	0.0377 (8)
H29A	0.4844	0.2687	0.1918	0.045*
C30	0.6608 (5)	0.3924 (3)	0.19263 (10)	0.0380 (8)
H30A	0.7540	0.3469	0.1832	0.046*
C31	0.6829 (5)	0.5059 (3)	0.20108 (10)	0.0370 (8)
H31A	0.7923	0.5386	0.1974	0.044*
C32	0.5480 (4)	0.5724 (3)	0.21471 (9)	0.0322 (8)
H32A	0.5647	0.6507	0.2194	0.039*

	U11	U22	U33	U12	U13	U23
O1	0.0538 (14)	0.0263 (12)	0.0191 (8)	0.0018 (12)	0.0009 (9)	−0.0037 (8)
O2	0.082 (2)	0.0251 (14)	0.0307 (10)	−0.0009 (14)	0.0073 (12)	−0.0026 (9)
O3	0.0499 (15)	0.0230 (12)	0.0293 (9)	−0.0013 (11)	0.0010 (10)	0.0023 (9)
O4	0.0520 (16)	0.0397 (16)	0.0535 (14)	0.0141 (14)	0.0082 (13)	0.0196 (12)
N1	0.0321 (14)	0.0203 (13)	0.0218 (10)	−0.0001 (12)	0.0004 (10)	0.0006 (9)
C1	0.076 (3)	0.048 (3)	0.0428 (18)	−0.004 (2)	−0.0177 (19)	−0.0079 (18)
C2	0.068 (3)	0.045 (2)	0.0335 (15)	0.007 (2)	0.0099 (16)	−0.0113 (16)
C3	0.110 (4)	0.036 (2)	0.0212 (14)	0.001 (3)	0.0062 (18)	−0.0010 (14)
C4	0.064 (2)	0.0310 (18)	0.0191 (12)	0.0043 (19)	−0.0019 (14)	−0.0052 (12)
C5	0.0381 (19)	0.0288 (19)	0.0237 (13)	0.0013 (15)	0.0017 (13)	−0.0013 (11)
C6	0.0274 (16)	0.0228 (16)	0.0242 (12)	0.0024 (14)	−0.0005 (12)	0.0012 (11)
C7	0.043 (2)	0.0315 (18)	0.0207 (12)	−0.0003 (16)	0.0026 (12)	0.0037 (11)
C8	0.049 (2)	0.0223 (16)	0.0293 (13)	−0.0013 (17)	−0.0012 (14)	0.0100 (12)
C9	0.054 (2)	0.0247 (18)	0.0318 (14)	−0.0017 (17)	−0.0003 (15)	0.0000 (13)
C10	0.0405 (19)	0.0249 (16)	0.0221 (12)	0.0023 (15)	0.0026 (13)	0.0004 (11)
C11	0.0259 (16)	0.0255 (17)	0.0242 (12)	−0.0002 (14)	−0.0001 (12)	0.0014 (11)
C12	0.0260 (15)	0.0254 (17)	0.0210 (12)	0.0008 (13)	0.0015 (11)	0.0004 (11)
C13	0.0290 (16)	0.0248 (17)	0.0213 (12)	0.0002 (14)	0.0009 (11)	0.0020 (11)
C14	0.0290 (15)	0.0266 (16)	0.0231 (11)	0.0021 (14)	0.0004 (11)	0.0035 (11)
C15	0.0267 (15)	0.0293 (17)	0.0249 (12)	−0.0001 (14)	0.0054 (11)	0.0031 (12)
C16	0.0367 (19)	0.0313 (19)	0.0376 (15)	0.0008 (16)	−0.0026 (14)	0.0036 (14)
C17	0.042 (2)	0.036 (2)	0.0379 (16)	−0.0098 (18)	−0.0070 (15)	−0.0027 (14)
C18	0.0364 (19)	0.042 (2)	0.0346 (15)	−0.0053 (17)	−0.0077 (14)	0.0086 (14)
C19	0.0358 (19)	0.033 (2)	0.0417 (16)	−0.0011 (17)	−0.0043 (14)	0.0122 (14)
C20	0.0325 (17)	0.0247 (17)	0.0337 (14)	−0.0007 (15)	−0.0009 (13)	0.0019 (12)
C21	0.0305 (16)	0.0230 (16)	0.0211 (11)	−0.0020 (14)	0.0011 (11)	0.0021 (10)
C22	0.0321 (17)	0.040 (2)	0.0333 (13)	−0.0024 (16)	−0.0023 (13)	0.0053 (14)
C23	0.0325 (19)	0.040 (2)	0.0367 (14)	0.0036 (17)	0.0016 (13)	0.0073 (14)
C24	0.0347 (18)	0.038 (2)	0.0263 (12)	0.0012 (17)	−0.0016 (12)	0.0075 (13)
C25	0.0288 (16)	0.0253 (16)	0.0200 (11)	−0.0006 (13)	−0.0015 (11)	0.0015 (10)
C26	0.0380 (18)	0.0260 (17)	0.0237 (12)	−0.0022 (15)	−0.0013 (12)	0.0045 (11)
C27	0.0352 (17)	0.0280 (17)	0.0184 (11)	0.0012 (15)	0.0039 (11)	0.0051 (11)
C28	0.047 (2)	0.0288 (18)	0.0267 (14)	−0.0082 (17)	0.0071 (14)	0.0011 (12)
C29	0.052 (2)	0.031 (2)	0.0301 (13)	−0.0011 (18)	0.0061 (15)	−0.0014 (13)
C30	0.046 (2)	0.039 (2)	0.0292 (14)	0.0069 (18)	0.0035 (14)	0.0000 (14)
C31	0.0362 (18)	0.042 (2)	0.0325 (14)	−0.0014 (17)	0.0020 (13)	0.0014 (14)
C32	0.043 (2)	0.0274 (18)	0.0257 (13)	−0.0058 (15)	0.0040 (13)	0.0018 (11)

O1—C5	1.330 (4)	C14—H14B	0.9900
O1—C4	1.495 (3)	C15—C20	1.383 (4)
O2—C5	1.188 (4)	C15—C16	1.384 (5)
O3—C13	1.207 (4)	C16—C17	1.396 (4)
O4—C24	1.219 (4)	C16—H16A	0.9500
N1—C13	1.415 (3)	C17—C18	1.363 (5)
N1—C5	1.416 (4)	C17—H17A	0.9500
N1—C6	1.434 (4)	C18—C19	1.393 (5)
C1—C4	1.510 (6)	C18—H18A	0.9500
C1—H1A	0.9800	C19—C20	1.391 (4)
C1—H1B	0.9800	C19—H19A	0.9500
C1—H1C	0.9800	C20—H20A	0.9500
C2—C4	1.503 (6)	C21—C25	1.529 (4)
C2—H2A	0.9800	C21—C22	1.544 (5)
C2—H2B	0.9800	C21—H21A	1.0000
C2—H2C	0.9800	C22—C23	1.526 (5)
C3—C4	1.523 (5)	C22—H22A	0.9900
C3—H3A	0.9800	C22—H22B	0.9900
C3—H3B	0.9800	C23—C24	1.496 (5)
C3—H3C	0.9800	C23—H23A	0.9900
C6—C7	1.384 (4)	C23—H23B	0.9900
C6—C11	1.398 (4)	C24—C25	1.481 (5)
C7—C8	1.391 (5)	C25—C26	1.342 (4)
C7—H7A	0.9500	C26—C27	1.478 (4)
C8—C9	1.381 (4)	C26—H26A	0.9500
C8—H8A	0.9500	C27—C28	1.395 (4)
C9—C10	1.396 (4)	C27—C32	1.396 (5)
C9—H9A	0.9500	C28—C29	1.384 (5)
C10—C11	1.375 (4)	C28—H28A	0.9500
C10—H10A	0.9500	C29—C30	1.379 (5)
C11—C12	1.496 (4)	C29—H29A	0.9500
C12—C13	1.526 (4)	C30—C31	1.382 (5)
C12—C21	1.560 (4)	C30—H30A	0.9500
C12—C14	1.564 (4)	C31—C32	1.379 (5)
C14—C15	1.513 (4)	C31—H31A	0.9500
C14—H14A	0.9900	C32—H32A	0.9500
C5—O1—C4	119.7 (2)	C20—C15—C16	119.0 (3)
C13—N1—C5	121.9 (3)	C20—C15—C14	120.6 (3)
C13—N1—C6	109.7 (2)	C16—C15—C14	120.4 (3)
C5—N1—C6	128.3 (2)	C15—C16—C17	120.6 (3)
C4—C1—H1A	109.5	C15—C16—H16A	119.7
C4—C1—H1B	109.5	C17—C16—H16A	119.7
H1A—C1—H1B	109.5	C18—C17—C16	119.8 (3)
C4—C1—H1C	109.5	C18—C17—H17A	120.1
H1A—C1—H1C	109.5	C16—C17—H17A	120.1
H1B—C1—H1C	109.5	C17—C18—C19	120.6 (3)
C4—C2—H2A	109.5	C17—C18—H18A	119.7
C4—C2—H2B	109.5	C19—C18—H18A	119.7
H2A—C2—H2B	109.5	C20—C19—C18	119.2 (3)
C4—C2—H2C	109.5	C20—C19—H19A	120.4
H2A—C2—H2C	109.5	C18—C19—H19A	120.4
H2B—C2—H2C	109.5	C15—C20—C19	120.7 (3)
C4—C3—H3A	109.5	C15—C20—H20A	119.6
C4—C3—H3B	109.5	C19—C20—H20A	119.6
H3A—C3—H3B	109.5	C25—C21—C22	102.8 (3)
C4—C3—H3C	109.5	C25—C21—C12	115.3 (2)
H3A—C3—H3C	109.5	C22—C21—C12	111.4 (2)
H3B—C3—H3C	109.5	C25—C21—H21A	109.1
O1—C4—C2	109.7 (3)	C22—C21—H21A	109.1
O1—C4—C1	109.3 (3)	C12—C21—H21A	109.1
C2—C4—C1	114.1 (3)	C23—C22—C21	107.5 (3)
O1—C4—C3	101.0 (2)	C23—C22—H22A	110.2
C2—C4—C3	111.3 (3)	C21—C22—H22A	110.2
C1—C4—C3	110.6 (3)	C23—C22—H22B	110.2
O2—C5—O1	127.7 (3)	C21—C22—H22B	110.2
O2—C5—N1	123.1 (3)	H22A—C22—H22B	108.5
O1—C5—N1	109.2 (3)	C24—C23—C22	104.8 (3)
C7—C6—C11	120.4 (3)	C24—C23—H23A	110.8
C7—C6—N1	130.9 (3)	C22—C23—H23A	110.8
C11—C6—N1	108.6 (2)	C24—C23—H23B	110.8
C6—C7—C8	118.1 (3)	C22—C23—H23B	110.8
C6—C7—H7A	120.9	H23A—C23—H23B	108.9
C8—C7—H7A	120.9	O4—C24—C25	125.2 (3)
C9—C8—C7	122.1 (3)	O4—C24—C23	125.2 (3)
C9—C8—H8A	119.0	C25—C24—C23	109.6 (3)
C7—C8—H8A	119.0	C26—C25—C24	119.6 (3)
C8—C9—C10	119.2 (3)	C26—C25—C21	131.5 (3)
C8—C9—H9A	120.4	C24—C25—C21	108.6 (2)
C10—C9—H9A	120.4	C25—C26—C27	128.6 (3)
C11—C10—C9	119.5 (3)	C25—C26—H26A	115.7
C11—C10—H10A	120.2	C27—C26—H26A	115.7
C9—C10—H10A	120.2	C28—C27—C32	118.2 (3)
C10—C11—C6	120.7 (3)	C28—C27—C26	122.8 (3)
C10—C11—C12	128.9 (2)	C32—C27—C26	119.0 (3)
C6—C11—C12	110.3 (3)	C29—C28—C27	120.4 (3)
C11—C12—C13	102.6 (2)	C29—C28—H28A	119.8
C11—C12—C21	111.6 (2)	C27—C28—H28A	119.8
C13—C12—C21	113.7 (2)	C30—C29—C28	121.0 (3)
C11—C12—C14	110.9 (2)	C30—C29—H29A	119.5
C13—C12—C14	106.1 (2)	C28—C29—H29A	119.5
C21—C12—C14	111.5 (2)	C29—C30—C31	118.9 (4)
O3—C13—N1	125.9 (3)	C29—C30—H30A	120.6
O3—C13—C12	126.1 (2)	C31—C30—H30A	120.6
N1—C13—C12	108.0 (2)	C32—C31—C30	120.8 (4)
C15—C14—C12	113.6 (2)	C32—C31—H31A	119.6
C15—C14—H14A	108.9	C30—C31—H31A	119.6
C12—C14—H14A	108.9	C31—C32—C27	120.7 (3)
C15—C14—H14B	108.9	C31—C32—H32A	119.6
C12—C14—H14B	108.9	C27—C32—H32A	119.6
H14A—C14—H14B	107.7
C5—O1—C4—C2	59.8 (4)	C21—C12—C14—C15	−178.5 (3)
C5—O1—C4—C1	−66.0 (4)	C12—C14—C15—C20	93.2 (3)
C5—O1—C4—C3	177.4 (3)	C12—C14—C15—C16	−86.4 (4)
C4—O1—C5—O2	1.7 (6)	C20—C15—C16—C17	−0.5 (5)
C4—O1—C5—N1	−178.0 (3)	C14—C15—C16—C17	179.2 (3)
C13—N1—C5—O2	5.8 (6)	C15—C16—C17—C18	0.8 (5)
C6—N1—C5—O2	−178.5 (4)	C16—C17—C18—C19	−0.2 (5)
C13—N1—C5—O1	−174.5 (3)	C17—C18—C19—C20	−0.7 (5)
C6—N1—C5—O1	1.2 (5)	C16—C15—C20—C19	−0.4 (5)
C13—N1—C6—C7	−174.9 (3)	C14—C15—C20—C19	179.9 (3)
C5—N1—C6—C7	8.9 (6)	C18—C19—C20—C15	1.0 (5)
C13—N1—C6—C11	1.4 (4)	C11—C12—C21—C25	179.9 (2)
C5—N1—C6—C11	−174.7 (3)	C13—C12—C21—C25	64.5 (3)
C11—C6—C7—C8	−0.9 (5)	C14—C12—C21—C25	−55.4 (3)
N1—C6—C7—C8	175.1 (3)	C11—C12—C21—C22	63.3 (3)
C6—C7—C8—C9	−0.2 (5)	C13—C12—C21—C22	−52.1 (4)
C7—C8—C9—C10	0.7 (6)	C14—C12—C21—C22	−172.0 (3)
C8—C9—C10—C11	−0.2 (5)	C25—C21—C22—C23	−25.9 (3)
C9—C10—C11—C6	−0.8 (5)	C12—C21—C22—C23	98.1 (3)
C9—C10—C11—C12	179.1 (3)	C21—C22—C23—C24	23.3 (3)
C7—C6—C11—C10	1.4 (5)	C22—C23—C24—O4	166.2 (3)
N1—C6—C11—C10	−175.4 (3)	C22—C23—C24—C25	−11.2 (3)
C7—C6—C11—C12	−178.5 (3)	O4—C24—C25—C26	−6.9 (5)
N1—C6—C11—C12	4.7 (4)	C23—C24—C25—C26	170.5 (3)
C10—C11—C12—C13	171.8 (3)	O4—C24—C25—C21	177.5 (3)
C6—C11—C12—C13	−8.3 (3)	C23—C24—C25—C21	−5.1 (3)
C10—C11—C12—C21	49.8 (4)	C22—C21—C25—C26	−156.1 (3)
C6—C11—C12—C21	−130.3 (3)	C12—C21—C25—C26	82.6 (4)
C10—C11—C12—C14	−75.3 (4)	C22—C21—C25—C24	18.9 (3)
C6—C11—C12—C14	104.6 (3)	C12—C21—C25—C24	−102.5 (3)
C5—N1—C13—O3	−7.8 (5)	C24—C25—C26—C27	−175.3 (3)
C6—N1—C13—O3	175.8 (3)	C21—C25—C26—C27	−0.8 (5)
C5—N1—C13—C12	169.7 (3)	C25—C26—C27—C28	44.4 (4)
C6—N1—C13—C12	−6.7 (3)	C25—C26—C27—C32	−135.6 (3)
C11—C12—C13—O3	−173.6 (3)	C32—C27—C28—C29	1.1 (4)
C21—C12—C13—O3	−53.0 (4)	C26—C27—C28—C29	−178.9 (3)
C14—C12—C13—O3	70.0 (4)	C27—C28—C29—C30	0.8 (4)
C11—C12—C13—N1	9.0 (3)	C28—C29—C30—C31	−1.3 (5)
C21—C12—C13—N1	129.6 (3)	C29—C30—C31—C32	−0.1 (5)
C14—C12—C13—N1	−107.5 (3)	C30—C31—C32—C27	2.0 (4)
C11—C12—C14—C15	−53.5 (3)	C28—C27—C32—C31	−2.5 (4)
C13—C12—C14—C15	57.2 (3)	C26—C27—C32—C31	177.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21A···O4i	1.00	2.37	3.295 (4)	153
C28—H28A···O4i	0.95	2.47	3.401 (4)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21A⋯O4i	1.00	2.37	3.295 (4)	153
C28—H28A⋯O4i	0.95	2.47	3.401 (4)	165

Symmetry code: (i) .