1-Acetyl-3-[1-(4-methoxyphenyl)-2-oxopropylidene]-1H-indol-2(3H)-one: a twinned crystal

The crystal of the title compound, C₂₀H₁₇NO₄, which was used for collecting intensity data was twinned. Each of the two crystallographically independent mol­ecules in the asymmetric unit has a planar indole moiety perpendicular to a planar oxo­propyl moiety. The distribution of the bonds at the central C atom joining the oxo­propyl, phenyl and indole substituents is also planar. The packing is stabilized by intermolecular C—H...O interactions, as well as by dipole–dipole and van der Waals interactions.

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

1-Acetyl-3-[1-(4-methoxyphenyl)-2-oxopropylidene]indol-2(3H)-one

Crystal data

C20H17NO4	F(000) = 1408
Mr = 335.35	Dx = 1.320 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 22.1109 (4) Å	Cell parameters from 7006 reflections
b = 6.9308 (1) Å	θ = 2.7–28.3°
c = 22.1109 (4) Å	µ = 0.09 mm^−1
β = 95.128 (1)°	T = 213 K
V = 3374.85 (10) Å^3	Block, yellow
Z = 8	0.40 × 0.32 × 0.24 mm

Data collection

Siemens SMART CCD area-detector diffractometer	3756 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.091
Graphite monochromator	θmax = 28.3°, θmin = 2.7°
Detector resolution: 8.33 pixels mm^-1	h = −28→29
ω scans	k = −7→9
20195 measured reflections	l = −29→25
8083 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.057	H-atom parameters constrained
wR(F^2) = 0.145	w = 1/[σ^2(Fo^2) + (0.0374P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.82	(Δ/σ)max < 0.001
8083 reflections	Δρmax = 0.29 e Å^−3
459 parameters	Δρmin = −0.25 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997a), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0094 (6)

Special details

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different φ angle (0, 88 and 180°) for the crystal and each exposure of 30 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1A	−0.09264 (12)	0.7608 (4)	0.58926 (13)	0.0579 (7)
O2A	0.09507 (10)	0.6865 (3)	0.62492 (10)	0.0461 (6)
O3A	0.20740 (12)	0.4531 (5)	0.57491 (11)	0.0737 (9)
O4A	0.28727 (11)	0.7046 (4)	0.30701 (10)	0.0590 (8)
N1A	0.00394 (11)	0.7346 (4)	0.56289 (12)	0.0328 (6)
C1A	0.06753 (15)	0.7072 (4)	0.57545 (16)	0.0352 (8)
C2A	−0.01026 (14)	0.7555 (4)	0.49878 (15)	0.0305 (8)
C3A	−0.06645 (15)	0.7808 (4)	0.46605 (17)	0.0402 (9)
H3A	−0.1019	0.7882	0.4856	0.048*
C4A	−0.06796 (16)	0.7946 (5)	0.40345 (17)	0.0437 (9)
H4A	−0.1050	0.8120	0.3806	0.052*
C5A	−0.01528 (16)	0.7829 (5)	0.37434 (16)	0.0414 (9)
H5A	−0.0176	0.7921	0.3322	0.050*
C6A	0.04098 (15)	0.7579 (5)	0.40648 (15)	0.0374 (8)
H6A	0.0761	0.7502	0.3864	0.045*
C7A	0.04355 (14)	0.7443 (4)	0.46986 (15)	0.0316 (8)
C8A	0.09422 (14)	0.7133 (4)	0.51589 (14)	0.0310 (8)
C9A	0.15347 (14)	0.6807 (4)	0.51172 (15)	0.0346 (8)
C10A	0.18476 (14)	0.6900 (5)	0.45500 (14)	0.0312 (8)
C11A	0.19128 (15)	0.8624 (5)	0.42523 (16)	0.0451 (9)
H11A	0.1726	0.9727	0.4386	0.054*
C12A	0.22548 (16)	0.8738 (5)	0.37530 (16)	0.0483 (9)
H12A	0.2304	0.9914	0.3561	0.058*
C13A	0.25178 (15)	0.7100 (5)	0.35484 (15)	0.0402 (8)
C14A	0.24525 (14)	0.5348 (5)	0.38356 (14)	0.0409 (8)
H14A	0.2632	0.4243	0.3694	0.049*
C15A	0.21192 (14)	0.5249 (5)	0.43346 (14)	0.0363 (8)
H15A	0.2076	0.4072	0.4528	0.044*
C16A	−0.03966 (18)	0.7395 (5)	0.60621 (17)	0.0418 (9)
C17A	−0.01676 (18)	0.7186 (5)	0.67159 (17)	0.0557 (11)
H17A	−0.0505	0.7154	0.6960	0.084*
H17B	0.0090	0.8261	0.6836	0.084*
H17C	0.0060	0.6009	0.6771	0.084*
C18A	0.19595 (16)	0.6263 (7)	0.56611 (16)	0.0502 (10)
C19A	0.22794 (19)	0.7818 (7)	0.60213 (19)	0.0815 (15)
H19A	0.2537	0.7259	0.6347	0.122*
H19B	0.1987	0.8647	0.6185	0.122*
H19C	0.2521	0.8554	0.5765	0.122*
C20A	0.2954 (2)	0.8809 (7)	0.27501 (19)	0.0851 (15)
H20A	0.3201	0.8573	0.2422	0.128*
H20B	0.3150	0.9740	0.3023	0.128*
H20C	0.2565	0.9295	0.2591	0.128*
O1B	0.40974 (12)	0.1951 (3)	0.58957 (11)	0.0519 (7)
O2B	0.37500 (10)	0.2012 (3)	0.40060 (10)	0.0417 (6)
O3B	0.43006 (13)	0.0159 (6)	0.28391 (15)	0.1079 (14)
O4B	0.69472 (10)	0.4121 (4)	0.22036 (11)	0.0563 (7)
N1B	0.43597 (11)	0.2207 (3)	0.49310 (11)	0.0299 (6)
C1B	0.42467 (15)	0.2196 (4)	0.42906 (14)	0.0315 (8)
C2B	0.49978 (15)	0.2457 (4)	0.50866 (14)	0.0302 (7)
C3B	0.53255 (16)	0.2492 (5)	0.56507 (15)	0.0378 (8)
H3B	0.5132	0.2342	0.6004	0.045*
C4B	0.59484 (16)	0.2754 (5)	0.56768 (16)	0.0435 (9)
H4B	0.6172	0.2796	0.6053	0.052*
C5B	0.62466 (17)	0.2956 (5)	0.51547 (17)	0.0437 (9)
H5B	0.6666	0.3125	0.5185	0.052*
C6B	0.59234 (15)	0.2908 (4)	0.45885 (15)	0.0358 (8)
H6B	0.6122	0.3049	0.4238	0.043*
C7B	0.52985 (14)	0.2647 (4)	0.45520 (14)	0.0279 (7)
C8B	0.48351 (14)	0.2461 (4)	0.40372 (14)	0.0289 (7)
C9B	0.48904 (15)	0.2395 (5)	0.34367 (15)	0.0398 (9)
C10B	0.54533 (15)	0.2778 (5)	0.31381 (14)	0.0368 (8)
C11B	0.56446 (16)	0.4644 (6)	0.30613 (18)	0.0573 (11)
H11B	0.5435	0.5654	0.3224	0.069*
C12B	0.61425 (16)	0.5048 (6)	0.27474 (18)	0.0621 (12)
H12B	0.6260	0.6320	0.2693	0.074*
C13B	0.64659 (15)	0.3560 (5)	0.25143 (14)	0.0394 (8)
C14B	0.62896 (15)	0.1707 (5)	0.25909 (16)	0.0464 (9)
H14B	0.6508	0.0700	0.2438	0.056*
C15B	0.57818 (16)	0.1315 (5)	0.28986 (16)	0.0485 (9)
H15B	0.5661	0.0042	0.2944	0.058*
C16B	0.39292 (16)	0.2031 (4)	0.53616 (16)	0.0364 (8)
C17B	0.32715 (16)	0.1989 (5)	0.51317 (17)	0.0482 (10)
H17D	0.3027	0.1986	0.5469	0.072*
H17E	0.3189	0.0846	0.4893	0.072*
H17F	0.3176	0.3107	0.4885	0.072*
C18B	0.43639 (18)	0.1879 (9)	0.29829 (18)	0.0711 (15)
C19B	0.3999 (2)	0.3445 (9)	0.2699 (2)	0.114 (2)
H19D	0.3785	0.2991	0.2330	0.170*
H19E	0.4259	0.4496	0.2610	0.170*
H19F	0.3712	0.3878	0.2972	0.170*
C20B	0.73453 (18)	0.2683 (6)	0.20192 (19)	0.0670 (12)
H20D	0.7655	0.3273	0.1803	0.101*
H20E	0.7121	0.1775	0.1759	0.101*
H20F	0.7531	0.2025	0.2370	0.101*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0334 (16)	0.0607 (18)	0.082 (2)	−0.0007 (12)	0.0185 (14)	0.0032 (15)
O2A	0.0418 (15)	0.0531 (17)	0.0431 (15)	−0.0020 (12)	0.0015 (12)	−0.0003 (12)
O3A	0.072 (2)	0.094 (2)	0.0545 (17)	0.0376 (18)	0.0022 (14)	0.0150 (16)
O4A	0.0522 (16)	0.085 (2)	0.0415 (15)	−0.0143 (14)	0.0113 (12)	0.0080 (14)
N1A	0.0240 (15)	0.0250 (15)	0.0505 (18)	−0.0022 (11)	0.0092 (13)	−0.0029 (12)
C1A	0.035 (2)	0.0218 (19)	0.049 (2)	−0.0036 (14)	0.0044 (17)	−0.0032 (15)
C2A	0.031 (2)	0.0149 (16)	0.046 (2)	−0.0033 (12)	0.0047 (16)	−0.0009 (14)
C3A	0.030 (2)	0.0246 (18)	0.065 (3)	−0.0023 (14)	0.0010 (17)	−0.0058 (17)
C4A	0.039 (2)	0.035 (2)	0.055 (2)	0.0011 (16)	−0.0069 (18)	−0.0026 (17)
C5A	0.046 (2)	0.032 (2)	0.045 (2)	−0.0047 (16)	−0.0063 (17)	0.0029 (16)
C6A	0.038 (2)	0.0286 (18)	0.045 (2)	−0.0049 (14)	0.0022 (17)	0.0026 (15)
C7A	0.033 (2)	0.0156 (16)	0.046 (2)	−0.0012 (13)	0.0019 (16)	−0.0001 (14)
C8A	0.033 (2)	0.0216 (17)	0.0390 (19)	−0.0028 (13)	0.0080 (15)	0.0002 (14)
C9A	0.0311 (19)	0.0316 (19)	0.0414 (19)	0.0013 (14)	0.0042 (15)	0.0018 (15)
C10A	0.0228 (17)	0.0337 (19)	0.0366 (19)	−0.0016 (13)	−0.0007 (14)	0.0014 (15)
C11A	0.041 (2)	0.037 (2)	0.057 (2)	0.0039 (16)	0.0074 (18)	0.0071 (18)
C12A	0.049 (2)	0.044 (2)	0.051 (2)	−0.0042 (18)	0.0001 (19)	0.0193 (19)
C13A	0.031 (2)	0.055 (2)	0.0353 (19)	−0.0093 (16)	0.0015 (15)	0.0030 (17)
C14A	0.0362 (19)	0.045 (2)	0.042 (2)	−0.0018 (16)	0.0044 (16)	−0.0044 (17)
C15A	0.0363 (18)	0.032 (2)	0.0397 (19)	−0.0044 (14)	0.0014 (15)	0.0012 (15)
C16A	0.052 (3)	0.0181 (17)	0.058 (2)	−0.0060 (15)	0.019 (2)	−0.0020 (16)
C17A	0.063 (3)	0.047 (2)	0.062 (3)	0.0014 (19)	0.028 (2)	0.003 (2)
C18A	0.032 (2)	0.078 (3)	0.042 (2)	0.011 (2)	0.0080 (16)	0.000 (2)
C19A	0.050 (3)	0.140 (5)	0.053 (3)	−0.023 (3)	−0.003 (2)	−0.019 (3)
C20A	0.083 (3)	0.111 (4)	0.063 (3)	−0.020 (3)	0.016 (2)	0.041 (3)
O1B	0.0644 (19)	0.0552 (17)	0.0373 (15)	0.0026 (13)	0.0108 (13)	−0.0002 (12)
O2B	0.0327 (14)	0.0517 (16)	0.0404 (13)	0.0000 (11)	0.0021 (11)	−0.0014 (11)
O3B	0.0463 (18)	0.181 (4)	0.098 (2)	−0.028 (2)	0.0156 (16)	−0.088 (3)
O4B	0.0428 (15)	0.0574 (17)	0.0722 (17)	−0.0010 (12)	0.0247 (13)	−0.0037 (14)
N1B	0.0312 (16)	0.0244 (14)	0.0346 (16)	0.0057 (11)	0.0053 (12)	−0.0008 (11)
C1B	0.037 (2)	0.0274 (19)	0.0301 (18)	0.0045 (14)	0.0025 (15)	−0.0006 (14)
C2B	0.038 (2)	0.0166 (16)	0.0356 (19)	0.0052 (13)	−0.0004 (15)	−0.0054 (13)
C3B	0.053 (2)	0.0247 (18)	0.035 (2)	0.0091 (15)	−0.0005 (17)	−0.0047 (14)
C4B	0.053 (3)	0.032 (2)	0.043 (2)	0.0078 (16)	−0.0119 (18)	−0.0065 (16)
C5B	0.040 (2)	0.030 (2)	0.058 (2)	−0.0003 (15)	−0.0082 (19)	−0.0044 (17)
C6B	0.034 (2)	0.0300 (19)	0.043 (2)	0.0001 (14)	0.0001 (16)	−0.0050 (15)
C7B	0.0323 (19)	0.0183 (16)	0.0330 (18)	0.0032 (13)	0.0022 (15)	−0.0035 (13)
C8B	0.0307 (18)	0.0227 (17)	0.0330 (18)	0.0004 (13)	0.0019 (14)	−0.0022 (13)
C9B	0.041 (2)	0.045 (2)	0.0329 (19)	−0.0033 (16)	−0.0019 (16)	−0.0004 (16)
C10B	0.034 (2)	0.047 (2)	0.0290 (18)	0.0000 (16)	−0.0006 (15)	−0.0046 (16)
C11B	0.050 (2)	0.048 (2)	0.079 (3)	−0.0097 (19)	0.029 (2)	−0.027 (2)
C12B	0.052 (2)	0.044 (2)	0.096 (3)	−0.0138 (18)	0.037 (2)	−0.020 (2)
C13B	0.0326 (19)	0.046 (2)	0.040 (2)	−0.0009 (16)	0.0060 (15)	−0.0001 (17)
C14B	0.035 (2)	0.046 (2)	0.060 (2)	0.0124 (17)	0.0129 (18)	0.0014 (19)
C15B	0.047 (2)	0.041 (2)	0.058 (2)	0.0058 (17)	0.0101 (19)	0.0125 (19)
C16B	0.046 (2)	0.0241 (18)	0.040 (2)	0.0055 (14)	0.0109 (17)	−0.0007 (15)
C17B	0.039 (2)	0.051 (2)	0.057 (2)	0.0046 (17)	0.0158 (19)	0.0040 (19)
C18B	0.036 (2)	0.138 (5)	0.040 (2)	−0.021 (3)	0.0108 (19)	−0.022 (3)
C19B	0.042 (3)	0.226 (7)	0.068 (3)	−0.016 (3)	−0.019 (2)	0.063 (4)
C20B	0.059 (3)	0.075 (3)	0.070 (3)	0.021 (2)	0.025 (2)	−0.004 (2)

Geometric parameters (Å, º)

O1A—C16A	1.207 (4)	O1B—C16B	1.207 (4)
O2A—C1A	1.212 (4)	O2B—C1B	1.223 (4)
O3A—C18A	1.239 (4)	O3B—C18B	1.238 (5)
O4A—C13A	1.373 (4)	O4B—C13B	1.373 (4)
O4A—C20A	1.432 (4)	O4B—C20B	1.414 (4)
N1A—C16A	1.419 (4)	N1B—C16B	1.410 (4)
N1A—C1A	1.421 (4)	N1B—C1B	1.416 (4)
N1A—C2A	1.432 (4)	N1B—C2B	1.433 (4)
C1A—C8A	1.491 (4)	C1B—C8B	1.473 (4)
C2A—C3A	1.392 (4)	C2B—C3B	1.385 (4)
C2A—C7A	1.402 (4)	C2B—C7B	1.413 (4)
C3A—C4A	1.385 (5)	C3B—C4B	1.385 (5)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—C5A	1.383 (5)	C4B—C5B	1.387 (5)
C4A—H4A	0.9300	C4B—H4B	0.9300
C5A—C6A	1.387 (4)	C5B—C6B	1.385 (5)
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—C7A	1.400 (4)	C6B—C7B	1.389 (4)
C6A—H6A	0.9300	C6B—H6B	0.9300
C7A—C8A	1.461 (4)	C7B—C8B	1.468 (4)
C8A—C9A	1.341 (4)	C8B—C9B	1.345 (4)
C9A—C10A	1.487 (4)	C9B—C10B	1.484 (4)
C9A—C18A	1.506 (5)	C9B—C18B	1.510 (5)
C10A—C11A	1.378 (4)	C10B—C11B	1.376 (5)
C10A—C15A	1.396 (4)	C10B—C15B	1.380 (5)
C11A—C12A	1.395 (5)	C11B—C12B	1.381 (4)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.371 (5)	C12B—C13B	1.381 (4)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.384 (4)	C13B—C14B	1.357 (4)
C14A—C15A	1.382 (4)	C14B—C15B	1.391 (5)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—H15A	0.9300	C15B—H15B	0.9300
C16A—C17A	1.495 (5)	C16B—C17B	1.497 (5)
C17A—H17A	0.9600	C17B—H17D	0.9600
C17A—H17B	0.9600	C17B—H17E	0.9600
C17A—H17C	0.9600	C17B—H17F	0.9600
C18A—C19A	1.481 (5)	C18B—C19B	1.460 (6)
C19A—H19A	0.9600	C19B—H19D	0.9600
C19A—H19B	0.9600	C19B—H19E	0.9600
C19A—H19C	0.9600	C19B—H19F	0.9600
C20A—H20A	0.9600	C20B—H20D	0.9600
C20A—H20B	0.9600	C20B—H20E	0.9600
C20A—H20C	0.9600	C20B—H20F	0.9600
C13A—O4A—C20A	117.6 (3)	C13B—O4B—C20B	118.4 (3)
C16A—N1A—C1A	126.3 (3)	C16B—N1B—C1B	127.3 (3)
C16A—N1A—C2A	124.3 (3)	C16B—N1B—C2B	123.9 (3)
C1A—N1A—C2A	109.4 (2)	C1B—N1B—C2B	108.8 (2)
O2A—C1A—N1A	126.9 (3)	O2B—C1B—N1B	125.8 (3)
O2A—C1A—C8A	126.4 (3)	O2B—C1B—C8B	126.9 (3)
N1A—C1A—C8A	106.6 (3)	N1B—C1B—C8B	107.3 (3)
C3A—C2A—C7A	121.6 (3)	C3B—C2B—C7B	120.3 (3)
C3A—C2A—N1A	129.4 (3)	C3B—C2B—N1B	130.0 (3)
C7A—C2A—N1A	109.0 (3)	C7B—C2B—N1B	109.7 (3)
C4A—C3A—C2A	118.0 (3)	C4B—C3B—C2B	118.5 (3)
C4A—C3A—H3A	121.0	C4B—C3B—H3B	120.7
C2A—C3A—H3A	121.0	C2B—C3B—H3B	120.7
C5A—C4A—C3A	121.0 (3)	C3B—C4B—C5B	121.6 (3)
C5A—C4A—H4A	119.5	C3B—C4B—H4B	119.2
C3A—C4A—H4A	119.5	C5B—C4B—H4B	119.2
C4A—C5A—C6A	121.5 (3)	C6B—C5B—C4B	120.3 (3)
C4A—C5A—H5A	119.2	C6B—C5B—H5B	119.8
C6A—C5A—H5A	119.2	C4B—C5B—H5B	119.8
C5A—C6A—C7A	118.4 (3)	C5B—C6B—C7B	119.1 (3)
C5A—C6A—H6A	120.8	C5B—C6B—H6B	120.5
C7A—C6A—H6A	120.8	C7B—C6B—H6B	120.5
C6A—C7A—C2A	119.5 (3)	C6B—C7B—C2B	120.2 (3)
C6A—C7A—C8A	131.8 (3)	C6B—C7B—C8B	132.7 (3)
C2A—C7A—C8A	108.6 (3)	C2B—C7B—C8B	107.0 (3)
C9A—C8A—C7A	132.1 (3)	C9B—C8B—C7B	130.5 (3)
C9A—C8A—C1A	121.5 (3)	C9B—C8B—C1B	122.2 (3)
C7A—C8A—C1A	106.3 (3)	C7B—C8B—C1B	107.2 (3)
C8A—C9A—C10A	125.6 (3)	C8B—C9B—C10B	126.0 (3)
C8A—C9A—C18A	122.1 (3)	C8B—C9B—C18B	122.1 (3)
C10A—C9A—C18A	112.3 (3)	C10B—C9B—C18B	112.0 (3)
C11A—C10A—C15A	118.8 (3)	C11B—C10B—C15B	117.7 (3)
C11A—C10A—C9A	121.1 (3)	C11B—C10B—C9B	120.1 (3)
C15A—C10A—C9A	119.9 (3)	C15B—C10B—C9B	122.0 (3)
C10A—C11A—C12A	121.0 (3)	C10B—C11B—C12B	121.3 (3)
C10A—C11A—H11A	119.5	C10B—C11B—H11B	119.3
C12A—C11A—H11A	119.5	C12B—C11B—H11B	119.3
C13A—C12A—C11A	119.4 (3)	C13B—C12B—C11B	119.9 (3)
C13A—C12A—H12A	120.3	C13B—C12B—H12B	120.0
C11A—C12A—H12A	120.3	C11B—C12B—H12B	120.0
C12A—C13A—O4A	124.5 (3)	C14B—C13B—O4B	125.0 (3)
C12A—C13A—C14A	120.7 (3)	C14B—C13B—C12B	119.7 (3)
O4A—C13A—C14A	114.8 (3)	O4B—C13B—C12B	115.2 (3)
C15A—C14A—C13A	119.7 (3)	C13B—C14B—C15B	119.9 (3)
C15A—C14A—H14A	120.2	C13B—C14B—H14B	120.0
C13A—C14A—H14A	120.2	C15B—C14B—H14B	120.0
C14A—C15A—C10A	120.5 (3)	C10B—C15B—C14B	121.3 (3)
C14A—C15A—H15A	119.7	C10B—C15B—H15B	119.3
C10A—C15A—H15A	119.7	C14B—C15B—H15B	119.3
O1A—C16A—N1A	119.5 (4)	O1B—C16B—N1B	119.8 (3)
O1A—C16A—C17A	123.2 (3)	O1B—C16B—C17B	122.4 (3)
N1A—C16A—C17A	117.3 (3)	N1B—C16B—C17B	117.8 (3)
C16A—C17A—H17A	109.5	C16B—C17B—H17D	109.5
C16A—C17A—H17B	109.5	C16B—C17B—H17E	109.5
H17A—C17A—H17B	109.5	H17D—C17B—H17E	109.5
C16A—C17A—H17C	109.5	C16B—C17B—H17F	109.5
H17A—C17A—H17C	109.5	H17D—C17B—H17F	109.5
H17B—C17A—H17C	109.5	H17E—C17B—H17F	109.5
O3A—C18A—C19A	122.6 (4)	O3B—C18B—C19B	124.0 (4)
O3A—C18A—C9A	118.2 (3)	O3B—C18B—C9B	117.5 (4)
C19A—C18A—C9A	118.7 (4)	C19B—C18B—C9B	118.2 (4)
C18A—C19A—H19A	109.5	C18B—C19B—H19D	109.5
C18A—C19A—H19B	109.5	C18B—C19B—H19E	109.5
H19A—C19A—H19B	109.5	H19D—C19B—H19E	109.5
C18A—C19A—H19C	109.5	C18B—C19B—H19F	109.5
H19A—C19A—H19C	109.5	H19D—C19B—H19F	109.5
H19B—C19A—H19C	109.5	H19E—C19B—H19F	109.5
O4A—C20A—H20A	109.5	O4B—C20B—H20D	109.5
O4A—C20A—H20B	109.5	O4B—C20B—H20E	109.5
H20A—C20A—H20B	109.5	H20D—C20B—H20E	109.5
O4A—C20A—H20C	109.5	O4B—C20B—H20F	109.5
H20A—C20A—H20C	109.5	H20D—C20B—H20F	109.5
H20B—C20A—H20C	109.5	H20E—C20B—H20F	109.5
C16A—N1A—C1A—O2A	−1.2 (5)	C16B—N1B—C1B—O2B	−0.7 (5)
C2A—N1A—C1A—O2A	179.3 (3)	C2B—N1B—C1B—O2B	−179.9 (3)
C16A—N1A—C1A—C8A	−179.9 (3)	C16B—N1B—C1B—C8B	178.9 (3)
C2A—N1A—C1A—C8A	0.5 (3)	C2B—N1B—C1B—C8B	−0.4 (3)
C16A—N1A—C2A—C3A	−1.1 (5)	C16B—N1B—C2B—C3B	3.2 (5)
C1A—N1A—C2A—C3A	178.5 (3)	C1B—N1B—C2B—C3B	−177.5 (3)
C16A—N1A—C2A—C7A	179.7 (3)	C16B—N1B—C2B—C7B	−178.1 (2)
C1A—N1A—C2A—C7A	−0.7 (3)	C1B—N1B—C2B—C7B	1.2 (3)
C7A—C2A—C3A—C4A	0.1 (4)	C7B—C2B—C3B—C4B	1.3 (4)
N1A—C2A—C3A—C4A	−179.0 (3)	N1B—C2B—C3B—C4B	179.8 (3)
C2A—C3A—C4A—C5A	0.2 (5)	C2B—C3B—C4B—C5B	−0.8 (5)
C3A—C4A—C5A—C6A	−0.3 (5)	C3B—C4B—C5B—C6B	0.3 (5)
C4A—C5A—C6A—C7A	0.0 (5)	C4B—C5B—C6B—C7B	−0.3 (5)
C5A—C6A—C7A—C2A	0.3 (4)	C5B—C6B—C7B—C2B	0.8 (4)
C5A—C6A—C7A—C8A	178.2 (3)	C5B—C6B—C7B—C8B	−177.5 (3)
C3A—C2A—C7A—C6A	−0.3 (4)	C3B—C2B—C7B—C6B	−1.3 (4)
N1A—C2A—C7A—C6A	178.9 (3)	N1B—C2B—C7B—C6B	179.9 (3)
C3A—C2A—C7A—C8A	−178.7 (3)	C3B—C2B—C7B—C8B	177.3 (3)
N1A—C2A—C7A—C8A	0.6 (3)	N1B—C2B—C7B—C8B	−1.5 (3)
C6A—C7A—C8A—C9A	−3.0 (6)	C6B—C7B—C8B—C9B	3.8 (6)
C2A—C7A—C8A—C9A	175.1 (3)	C2B—C7B—C8B—C9B	−174.6 (3)
C6A—C7A—C8A—C1A	−178.3 (3)	C6B—C7B—C8B—C1B	179.6 (3)
C2A—C7A—C8A—C1A	−0.3 (3)	C2B—C7B—C8B—C1B	1.2 (3)
O2A—C1A—C8A—C9A	5.1 (5)	O2B—C1B—C8B—C9B	−4.7 (5)
N1A—C1A—C8A—C9A	−176.1 (3)	N1B—C1B—C8B—C9B	175.7 (3)
O2A—C1A—C8A—C7A	−178.9 (3)	O2B—C1B—C8B—C7B	179.0 (3)
N1A—C1A—C8A—C7A	−0.1 (3)	N1B—C1B—C8B—C7B	−0.5 (3)
C7A—C8A—C9A—C10A	7.4 (5)	C7B—C8B—C9B—C10B	−9.2 (6)
C1A—C8A—C9A—C10A	−177.8 (3)	C1B—C8B—C9B—C10B	175.5 (3)
C7A—C8A—C9A—C18A	−171.6 (3)	C7B—C8B—C9B—C18B	170.0 (4)
C1A—C8A—C9A—C18A	3.2 (5)	C1B—C8B—C9B—C18B	−5.3 (5)
C8A—C9A—C10A—C11A	67.2 (4)	C8B—C9B—C10B—C11B	−77.7 (5)
C18A—C9A—C10A—C11A	−113.6 (4)	C18B—C9B—C10B—C11B	103.0 (4)
C8A—C9A—C10A—C15A	−117.4 (4)	C8B—C9B—C10B—C15B	106.0 (4)
C18A—C9A—C10A—C15A	61.7 (4)	C18B—C9B—C10B—C15B	−73.3 (5)
C15A—C10A—C11A—C12A	−1.5 (5)	C15B—C10B—C11B—C12B	1.0 (6)
C9A—C10A—C11A—C12A	174.0 (3)	C9B—C10B—C11B—C12B	−175.4 (3)
C10A—C11A—C12A—C13A	1.5 (5)	C10B—C11B—C12B—C13B	−1.3 (6)
C11A—C12A—C13A—O4A	−178.7 (3)	C20B—O4B—C13B—C14B	−9.4 (5)
C11A—C12A—C13A—C14A	−0.7 (5)	C20B—O4B—C13B—C12B	172.0 (3)
C20A—O4A—C13A—C12A	−2.4 (5)	C11B—C12B—C13B—C14B	0.5 (6)
C20A—O4A—C13A—C14A	179.5 (3)	C11B—C12B—C13B—O4B	179.2 (3)
C12A—C13A—C14A—C15A	−0.1 (5)	O4B—C13B—C14B—C15B	−177.9 (3)
O4A—C13A—C14A—C15A	178.1 (3)	C12B—C13B—C14B—C15B	0.6 (5)
C13A—C14A—C15A—C10A	0.1 (5)	C11B—C10B—C15B—C14B	0.1 (5)
C11A—C10A—C15A—C14A	0.7 (5)	C9B—C10B—C15B—C14B	176.4 (3)
C9A—C10A—C15A—C14A	−174.8 (3)	C13B—C14B—C15B—C10B	−0.9 (5)
C1A—N1A—C16A—O1A	−178.8 (3)	C1B—N1B—C16B—O1B	175.6 (3)
C2A—N1A—C16A—O1A	0.7 (5)	C2B—N1B—C16B—O1B	−5.3 (4)
C1A—N1A—C16A—C17A	1.5 (5)	C1B—N1B—C16B—C17B	−5.5 (4)
C2A—N1A—C16A—C17A	−179.0 (3)	C2B—N1B—C16B—C17B	173.6 (3)
C8A—C9A—C18A—O3A	96.8 (4)	C8B—C9B—C18B—O3B	−91.7 (5)
C10A—C9A—C18A—O3A	−82.3 (4)	C10B—C9B—C18B—O3B	87.6 (4)
C8A—C9A—C18A—C19A	−90.6 (4)	C8B—C9B—C18B—C19B	94.0 (5)
C10A—C9A—C18A—C19A	90.2 (4)	C10B—C9B—C18B—C19B	−86.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3A—H3A···O1A	0.93	2.29	2.839 (5)	117
C3B—H3B···O1B	0.93	2.29	2.841 (4)	117
C20B—H20E···O3A^i	0.96	2.40	3.209 (5)	141
C20B—H20F···O4B^ii	0.96	2.47	3.319 (5)	148

Symmetry codes: (i) x+1/2, −y+1/2, z−1/2; (ii) −x+3/2, y−1/2, −z+1/2.