(Z)-2-(4-Methoxy­phen­yl)-3-phenyl­acrylonitrile

A new dipolarophile for the construction of bioactive isoxazoli(di)nes, (Z)-2-(4-methoxy­phen­yl)-3-phenyl­acrylo­nitrile, C₁₆H₁₃NO, was synthesized by the base-catalysed reaction of benzaldehyde with 4-methoxy­phenyl­acetonitrile. The olefinic bond connecting the 4-methoxy­phenyl­acetonitrile and the phenyl groups has Z geometry. There are two mol­ecules in the asymmetric unit. In the crystal structure, the mol­ecules are linked by C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.046
• wR factor = 0.144
• Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.89

Author Response: ...We have collected data on kappa IP diffractometer and processed using Denzo; and it is known that the DENZO image processing package has problems with certain strong reflections. They are often excluded from the data set leading to a lower value for the above parameter.

Alert level B
REFLT03_ALERT_3_B  Reflection count < 90% complete (theta max?)
           From the CIF: _diffrn_reflns_theta_max           25.02
           From the CIF: _diffrn_reflns_theta_full          25.02
           From the CIF: _reflns_number_total               3954
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         4427
           Completeness (_total/calc)             89.32%
PLAT022_ALERT_3_B Ratio Unique / Expected Reflections too Low ....       0.89

Alert level C
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C9     -   C10    ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C9A    -   C10A   ...       1.44 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          3

   1 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: XPRESS (MacScience, 2002); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and ORTEPII (Johnson, 1976); software used to prepare material for publication: PLATON.

(Z)-2-(4-methoxyphenyl)-3-phenylacrylonitrile

Crystal data

C16H13NO	Z = 4
Mr = 235.27	F(000) = 496
Triclinic, P1	Dx = 1.247 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.362 (9) Å	Cell parameters from 6395 reflections
b = 11.859 (12) Å	θ = 2.2–25.0°
c = 14.481 (13) Å	µ = 0.08 mm^−1
α = 89.658 (6)°	T = 295 K
β = 82.467 (6)°	Block, pale yellow
γ = 89.604 (5)°	0.25 × 0.20 × 0.20 mm
V = 1253 (2) Å^3

Data collection

MacScience DIPLabo 32001 diffractometer	3150 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
Graphite monochromator	θmax = 25.0°, θmin = 2.2°
Detector resolution: 10.0 pixels mm^-1	h = −8→8
ω scans	k = −14→14
6395 measured reflections	l = −17→17
3954 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)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.144	w = 1/[σ^2(Fo^2) + (0.0739P)^2 + 0.1197P] where P = (Fo^2 + 2Fc^2)/3
S = 1.15	(Δ/σ)max < 0.001
3954 reflections	Δρmax = 0.23 e Å^−3
328 parameters	Δρmin = −0.22 e Å^−3
0 restraints	Extinction correction: SHELXL97
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.085 (8)

Special details

Experimental. ¹HNMR (CDCl₃):3.75 (s, 3H, O—CH3), 6.81–6.92 (dd, 2H, Ar—H) 7.45–7.55 (dd, 2H, Ar—H), 6.98–7.7 (m,5H, Ar—H), 7.41 (s, 1H, CH=C—Ar).

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F^2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2, conventional R-factors R are based on F, with F set to zero for negative F^2. The observed criterion of F^2 > σ(F^2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2 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
O7	0.1561 (2)	0.25325 (11)	0.43994 (9)	0.0596 (5)
N11	0.2865 (4)	0.11652 (17)	−0.03573 (14)	0.0866 (9)
C1	0.2740 (3)	0.36808 (16)	0.30558 (13)	0.0502 (6)
C2	0.3033 (3)	0.37730 (16)	0.20977 (13)	0.0498 (6)
C3	0.2488 (2)	0.29425 (15)	0.15226 (12)	0.0438 (6)
C4	0.1652 (3)	0.19868 (15)	0.19514 (13)	0.0478 (6)
C5	0.1347 (3)	0.18845 (15)	0.29030 (13)	0.0487 (6)
C6	0.1887 (3)	0.27273 (15)	0.34623 (12)	0.0461 (6)
C8	0.2019 (3)	0.3394 (2)	0.50046 (14)	0.0671 (8)
C9	0.2710 (3)	0.30729 (15)	0.04951 (12)	0.0466 (6)
C10	0.2802 (3)	0.20279 (17)	−0.00126 (14)	0.0559 (7)
C12	0.2719 (3)	0.40719 (16)	0.00411 (13)	0.0499 (6)
C13	0.2828 (2)	0.43245 (15)	−0.09515 (12)	0.0451 (6)
C14	0.2075 (3)	0.53465 (16)	−0.12065 (14)	0.0527 (7)
C15	0.2049 (3)	0.56245 (18)	−0.21295 (15)	0.0591 (7)
C16	0.2793 (3)	0.49089 (18)	−0.28210 (14)	0.0586 (7)
C17	0.3571 (3)	0.39064 (18)	−0.25829 (13)	0.0577 (7)
C18	0.3599 (3)	0.36145 (17)	−0.16606 (13)	0.0525 (7)
O7A	0.1562 (2)	0.75085 (12)	0.03673 (9)	0.0646 (5)
N11A	0.2874 (3)	0.61782 (17)	0.49444 (14)	0.0844 (9)
C1A	0.2536 (3)	0.87160 (16)	0.15656 (13)	0.0512 (7)
C2A	0.2786 (3)	0.88254 (15)	0.24860 (13)	0.0492 (6)
C3A	0.2332 (2)	0.79697 (15)	0.31357 (12)	0.0439 (6)
C4A	0.1605 (3)	0.69860 (15)	0.28150 (13)	0.0485 (6)
C5A	0.1338 (3)	0.68669 (15)	0.19013 (13)	0.0513 (7)
C6A	0.1814 (3)	0.77283 (16)	0.12636 (13)	0.0484 (6)
C8A	0.2076 (4)	0.8352 (2)	−0.03165 (15)	0.0734 (9)
C9A	0.2594 (2)	0.80970 (15)	0.41288 (12)	0.0458 (6)
C10A	0.2746 (3)	0.70446 (17)	0.46127 (14)	0.0557 (7)
C12A	0.2644 (3)	0.90815 (16)	0.45773 (13)	0.0499 (6)
C13A	0.2838 (3)	0.93189 (16)	0.55495 (13)	0.0476 (6)
C14A	0.2151 (3)	1.03428 (16)	0.59164 (14)	0.0556 (7)
C15A	0.2191 (3)	1.06011 (18)	0.68446 (15)	0.0613 (8)
C16A	0.2950 (3)	0.98571 (19)	0.74150 (14)	0.0604 (8)
C17A	0.3690 (3)	0.88529 (19)	0.70585 (14)	0.0606 (8)
C18A	0.3639 (3)	0.85870 (17)	0.61387 (14)	0.0554 (7)
H1	0.31110	0.42520	0.34250	0.0600*
H2	0.36130	0.44110	0.18290	0.0600*
H4	0.12950	0.14080	0.15850	0.0570*
H5	0.07730	0.12450	0.31740	0.0580*
H8A	0.33010	0.35600	0.48700	0.1010*
H8B	0.17490	0.31440	0.56390	0.1010*
H8C	0.13160	0.40610	0.49140	0.1010*
H12	0.26450	0.47020	0.04240	0.0600*
H14	0.15850	0.58470	−0.07460	0.0630*
H15	0.15220	0.63030	−0.22850	0.0710*
H16	0.27730	0.50990	−0.34440	0.0700*
H17	0.40830	0.34200	−0.30490	0.0690*
H18	0.41390	0.29370	−0.15120	0.0630*
H8A1	0.13670	0.90230	−0.01650	0.1100*
H1A	0.28510	0.93030	0.11480	0.0610*
H8A2	0.18550	0.80850	−0.09160	0.1100*
H2A	0.32730	0.94920	0.26800	0.0590*
H8A3	0.33550	0.85160	−0.03310	0.1100*
H4A	0.12930	0.63960	0.32310	0.0580*
H5A	0.08350	0.62050	0.17080	0.0620*
H12A	0.25380	0.97180	0.42090	0.0600*
H14A	0.16570	1.08600	0.55320	0.0670*
H15A	0.17020	1.12810	0.70820	0.0740*
H16A	0.29670	1.00280	0.80400	0.0720*
H17A	0.42250	0.83530	0.74420	0.0730*
H18A	0.41460	0.79090	0.59060	0.0660*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O7	0.0807 (10)	0.0544 (8)	0.0437 (8)	−0.0114 (7)	−0.0075 (6)	0.0013 (6)
N11	0.134 (2)	0.0552 (12)	0.0659 (13)	−0.0109 (12)	0.0055 (11)	−0.0119 (10)
C1	0.0586 (12)	0.0450 (10)	0.0482 (11)	−0.0094 (8)	−0.0111 (8)	−0.0042 (8)
C2	0.0553 (12)	0.0451 (10)	0.0496 (11)	−0.0112 (8)	−0.0089 (8)	0.0020 (8)
C3	0.0444 (10)	0.0414 (9)	0.0458 (10)	−0.0019 (7)	−0.0065 (7)	−0.0024 (8)
C4	0.0533 (11)	0.0397 (10)	0.0516 (11)	−0.0048 (8)	−0.0110 (8)	−0.0051 (8)
C5	0.0539 (11)	0.0408 (10)	0.0515 (11)	−0.0064 (8)	−0.0076 (8)	0.0034 (8)
C6	0.0496 (11)	0.0463 (10)	0.0427 (10)	0.0001 (8)	−0.0077 (7)	0.0019 (8)
C8	0.0821 (16)	0.0701 (14)	0.0492 (12)	−0.0108 (12)	−0.0079 (10)	−0.0083 (11)
C9	0.0476 (11)	0.0444 (10)	0.0480 (11)	−0.0027 (8)	−0.0061 (7)	−0.0061 (8)
C10	0.0696 (14)	0.0480 (11)	0.0489 (11)	−0.0055 (9)	−0.0030 (9)	−0.0024 (9)
C12	0.0556 (12)	0.0455 (10)	0.0487 (11)	−0.0013 (8)	−0.0073 (8)	−0.0065 (8)
C13	0.0465 (10)	0.0458 (10)	0.0432 (10)	−0.0051 (8)	−0.0058 (7)	−0.0015 (8)
C14	0.0610 (13)	0.0442 (10)	0.0522 (12)	−0.0017 (8)	−0.0044 (8)	−0.0008 (9)
C15	0.0650 (13)	0.0507 (11)	0.0625 (13)	−0.0010 (9)	−0.0120 (10)	0.0078 (10)
C16	0.0626 (13)	0.0676 (13)	0.0471 (11)	−0.0091 (10)	−0.0123 (9)	0.0085 (10)
C17	0.0611 (13)	0.0665 (13)	0.0443 (11)	0.0008 (10)	−0.0017 (8)	−0.0062 (10)
C18	0.0538 (12)	0.0544 (11)	0.0487 (11)	0.0052 (9)	−0.0046 (8)	−0.0012 (9)
O7A	0.0940 (12)	0.0549 (8)	0.0470 (8)	−0.0125 (7)	−0.0166 (7)	−0.0034 (7)
N11A	0.128 (2)	0.0563 (12)	0.0757 (14)	−0.0079 (11)	−0.0390 (12)	0.0090 (11)
C1A	0.0630 (13)	0.0420 (10)	0.0481 (11)	−0.0068 (8)	−0.0053 (8)	0.0002 (8)
C2A	0.0541 (11)	0.0426 (10)	0.0513 (11)	−0.0097 (8)	−0.0080 (8)	−0.0065 (8)
C3A	0.0417 (10)	0.0420 (9)	0.0483 (10)	0.0003 (7)	−0.0073 (7)	−0.0013 (8)
C4A	0.0526 (11)	0.0406 (10)	0.0523 (11)	−0.0047 (8)	−0.0062 (8)	0.0010 (8)
C5A	0.0590 (12)	0.0407 (10)	0.0551 (12)	−0.0090 (8)	−0.0101 (9)	−0.0059 (9)
C6A	0.0537 (11)	0.0466 (10)	0.0458 (10)	−0.0003 (8)	−0.0095 (8)	−0.0066 (8)
C8A	0.0949 (19)	0.0763 (15)	0.0517 (13)	−0.0155 (13)	−0.0194 (11)	0.0051 (12)
C9A	0.0453 (10)	0.0447 (10)	0.0480 (11)	−0.0022 (8)	−0.0082 (7)	0.0007 (8)
C10A	0.0672 (14)	0.0492 (11)	0.0532 (12)	−0.0058 (9)	−0.0168 (9)	−0.0012 (10)
C12A	0.0552 (12)	0.0479 (10)	0.0473 (11)	−0.0013 (8)	−0.0092 (8)	0.0004 (9)
C13A	0.0472 (11)	0.0481 (10)	0.0477 (11)	−0.0045 (8)	−0.0066 (8)	−0.0023 (8)
C14A	0.0634 (13)	0.0442 (10)	0.0604 (12)	−0.0040 (9)	−0.0125 (9)	−0.0045 (9)
C15A	0.0662 (14)	0.0535 (12)	0.0640 (13)	−0.0043 (10)	−0.0071 (10)	−0.0158 (10)
C16A	0.0648 (14)	0.0708 (14)	0.0461 (11)	−0.0099 (10)	−0.0087 (9)	−0.0083 (10)
C17A	0.0643 (14)	0.0675 (13)	0.0531 (12)	0.0002 (10)	−0.0188 (9)	−0.0027 (10)
C18A	0.0595 (13)	0.0543 (11)	0.0544 (12)	0.0083 (9)	−0.0150 (9)	−0.0083 (9)

Geometric parameters (Å, º)

O7—C6	1.365 (2)	C16—H16	0.9306
O7—C8	1.421 (3)	C17—H17	0.9302
O7A—C8A	1.421 (3)	C18—H18	0.9305
O7A—C6A	1.362 (2)	C1A—C2A	1.376 (3)
N11—C10	1.139 (3)	C1A—C6A	1.386 (3)
N11A—C10A	1.140 (3)	C2A—C3A	1.392 (3)
C1—C2	1.380 (3)	C3A—C4A	1.394 (3)
C1—C6	1.387 (3)	C3A—C9A	1.485 (2)
C2—C3	1.388 (3)	C4A—C5A	1.371 (3)
C3—C4	1.396 (3)	C5A—C6A	1.389 (3)
C3—C9	1.483 (2)	C9A—C10A	1.439 (3)
C4—C5	1.372 (3)	C9A—C12A	1.342 (3)
C5—C6	1.383 (3)	C12A—C13A	1.463 (3)
C9—C10	1.441 (3)	C13A—C14A	1.393 (3)
C9—C12	1.351 (3)	C13A—C18A	1.395 (3)
C12—C13	1.458 (3)	C14A—C15A	1.384 (3)
C13—C14	1.397 (3)	C15A—C16A	1.371 (3)
C13—C18	1.392 (3)	C16A—C17A	1.381 (3)
C14—C15	1.377 (3)	C17A—C18A	1.376 (3)
C15—C16	1.372 (3)	C1A—H1A	0.9298
C16—C17	1.378 (3)	C2A—H2A	0.9303
C17—C18	1.380 (3)	C4A—H4A	0.9307
C1—H1	0.9298	C5A—H5A	0.9303
C2—H2	0.9293	C8A—H8A1	0.9592
C4—H4	0.9301	C8A—H8A2	0.9599
C5—H5	0.9301	C8A—H8A3	0.9603
C8—H8A	0.9599	C12A—H12A	0.9304
C8—H8B	0.9597	C14A—H14A	0.9296
C8—H8C	0.9600	C15A—H15A	0.9299
C12—H12	0.9302	C16A—H16A	0.9304
C14—H14	0.9305	C17A—H17A	0.9302
C15—H15	0.9301	C18A—H18A	0.9303
O7···C10A^i	3.339 (3)	C16A···H2A^vii	2.8766
O7A···C10^ii	3.360 (3)	C17A···H2A^vii	3.0474
O7···H14A^iii	2.5727	H1···H8A	2.2641
O7A···H14	2.5519	H1···C8	2.5328
N11···C8A^iii	3.389 (3)	H1···H8C	2.3871
N11A···C8	3.364 (3)	H8A1···N11^viii	2.7744
N11A···C18A	3.436 (3)	H8A1···H1A	2.3401
N11···H4	2.9125	H8A1···C1A	2.7756
N11···H16A^iv	2.6835	H1A···H8A1	2.3401
N11···H8A1^iii	2.7744	H1A···H8A3	2.3252
N11···H18	2.7685	H1A···C8A	2.5396
N11A···H4A	2.8850	H2···H12	2.2660
N11A···H16^v	2.6477	H2···C12	2.7859
N11A···H18A	2.7261	H2A···C17A^vii	3.0474
N11A···H8C	2.7706	H2A···H12A	2.2267
N11A···H8A^vi	2.8827	H2A···C16A^vii	2.8766
C2A···C16A^vii	3.536 (3)	H2A···C12A	2.7665
C8···N11A	3.364 (3)	H8A3···H1A	2.3252
C8···C10A^i	3.521 (3)	H8A3···C1A	2.7449
C8A···N11^viii	3.389 (3)	H8A3···C10^ix	3.0014
C8A···C10^ii	3.591 (4)	H4···C10	2.5380
C10···C8A^ii	3.591 (4)	H4···N11	2.9125
C10···C18	3.029 (3)	H4A···C10A	2.5160
C10···O7A^ii	3.360 (3)	H4A···N11A	2.8850
C10A···C18A	3.018 (3)	H5···C14A^i	3.0327
C10A···C8^i	3.521 (3)	H5A···C15^ii	3.0489
C10A···O7^i	3.339 (3)	H5A···C14^ii	2.9968
C16A···C2A^vii	3.536 (3)	H8A···H1	2.2641
C18···C10	3.029 (3)	H8A···C1	2.7152
C18A···C10A	3.018 (3)	H8A···N11A^vi	2.8827
C18A···N11A	3.436 (3)	H8C···C1	2.7949
C1···H8C	2.7949	H8C···H1	2.3871
C1···H8A	2.7152	H8C···N11A	2.7706
C1A···H8A1	2.7756	H12···H14	2.3723
C1A···H8A3	2.7449	H12···H2	2.2660
C2···H12	2.7046	H12···C2	2.7046
C2A···H12A	2.6998	H12A···H2A	2.2267
C3A···H17^ix	3.0908	H12A···H14A	2.3703
C4···H15^ii	3.0752	H12A···C2A	2.6998
C8···H1	2.5328	H14···H12	2.3723
C8A···H1A	2.5396	H14···C8A	3.0722
C8A···H16A^x	3.0979	H14···O7A	2.5519
C8A···H14	3.0722	H14A···H12A	2.3703
C9···H18	2.9634	H14A···O7^viii	2.5727
C9A···H18A	2.9562	H15···C4^ii	3.0752
C10···H8A3^ix	3.0014	H16···N11A^x	2.6477
C10···H4	2.5380	H16A···N11^xi	2.6835
C10···H18	2.5044	H16A···C8A^v	3.0979
C10A···H17^ix	3.0809	H17···C10A^ix	3.0809
C10A···H18A	2.4828	H17···C3A^ix	3.0908
C10A···H4A	2.5160	H18···C9	2.9634
C12···H2	2.7859	H18···C10	2.5044
C12A···H2A	2.7665	H18···N11	2.7685
C14···H5A^ii	2.9968	H18A···N11A	2.7261
C14A···H5^i	3.0327	H18A···C9A	2.9562
C15···H5A^ii	3.0489	H18A···C10A	2.4828
C6—O7—C8	117.96 (15)	C17—C18—H18	119.68
C6A—O7A—C8A	117.91 (16)	C2A—C1A—C6A	119.79 (17)
C2—C1—C6	119.32 (18)	C1A—C2A—C3A	122.04 (17)
C1—C2—C3	122.05 (18)	C2A—C3A—C4A	117.06 (16)
C2—C3—C4	117.32 (16)	C2A—C3A—C9A	121.72 (16)
C4—C3—C9	120.72 (16)	C4A—C3A—C9A	121.21 (16)
C2—C3—C9	121.91 (16)	C3A—C4A—C5A	121.58 (17)
C3—C4—C5	121.28 (17)	C4A—C5A—C6A	120.37 (18)
C4—C5—C6	120.38 (17)	O7A—C6A—C1A	125.07 (17)
O7—C6—C1	124.52 (17)	O7A—C6A—C5A	115.76 (17)
C1—C6—C5	119.63 (17)	C1A—C6A—C5A	119.15 (17)
O7—C6—C5	115.83 (16)	C3A—C9A—C10A	113.98 (16)
C3—C9—C10	114.71 (16)	C3A—C9A—C12A	125.35 (17)
C10—C9—C12	120.58 (17)	C10A—C9A—C12A	120.65 (17)
C3—C9—C12	124.59 (16)	N11A—C10A—C9A	175.8 (2)
N11—C10—C9	175.4 (2)	C9A—C12A—C13A	130.66 (18)
C9—C12—C13	130.57 (17)	C12A—C13A—C14A	117.64 (18)
C12—C13—C18	124.78 (17)	C12A—C13A—C18A	124.66 (18)
C14—C13—C18	117.79 (17)	C14A—C13A—C18A	117.69 (18)
C12—C13—C14	117.42 (16)	C13A—C14A—C15A	121.02 (19)
C13—C14—C15	120.97 (18)	C14A—C15A—C16A	120.2 (2)
C14—C15—C16	120.6 (2)	C15A—C16A—C17A	119.74 (19)
C15—C16—C17	119.28 (19)	C16A—C17A—C18A	120.3 (2)
C16—C17—C18	120.79 (19)	C13A—C18A—C17A	120.98 (19)
C13—C18—C17	120.60 (19)	C2A—C1A—H1A	120.06
C2—C1—H1	120.31	C6A—C1A—H1A	120.15
C6—C1—H1	120.36	C1A—C2A—H2A	118.98
C1—C2—H2	118.97	C3A—C2A—H2A	118.98
C3—C2—H2	118.98	C3A—C4A—H4A	119.22
C5—C4—H4	119.32	C5A—C4A—H4A	119.20
C3—C4—H4	119.40	C4A—C5A—H5A	119.77
C4—C5—H5	119.84	C6A—C5A—H5A	119.86
C6—C5—H5	119.78	O7A—C8A—H8A1	109.50
O7—C8—H8B	109.49	O7A—C8A—H8A2	109.45
O7—C8—H8C	109.48	O7A—C8A—H8A3	109.44
O7—C8—H8A	109.50	H8A1—C8A—H8A2	109.48
H8A—C8—H8C	109.45	H8A1—C8A—H8A3	109.55
H8B—C8—H8C	109.43	H8A2—C8A—H8A3	109.42
H8A—C8—H8B	109.47	C9A—C12A—H12A	114.68
C9—C12—H12	114.75	C13A—C12A—H12A	114.66
C13—C12—H12	114.68	C13A—C14A—H14A	119.47
C15—C14—H14	119.52	C15A—C14A—H14A	119.51
C13—C14—H14	119.51	C14A—C15A—H15A	119.96
C14—C15—H15	119.68	C16A—C15A—H15A	119.88
C16—C15—H15	119.76	C15A—C16A—H16A	120.14
C17—C16—H16	120.37	C17A—C16A—H16A	120.11
C15—C16—H16	120.36	C16A—C17A—H17A	119.86
C16—C17—H17	119.63	C18A—C17A—H17A	119.80
C18—C17—H17	119.59	C13A—C18A—H18A	119.47
C13—C18—H18	119.73	C17A—C18A—H18A	119.55
C8—O7—C6—C5	−177.35 (18)	C15—C16—C17—C18	0.4 (3)
C8—O7—C6—C1	4.2 (3)	C16—C17—C18—C13	0.5 (3)
C8A—O7A—C6A—C5A	−178.3 (2)	C2A—C1A—C6A—C5A	0.6 (3)
C8A—O7A—C6A—C1A	0.0 (3)	C2A—C1A—C6A—O7A	−177.7 (2)
C2—C1—C6—C5	0.1 (3)	C6A—C1A—C2A—C3A	−0.1 (3)
C2—C1—C6—O7	178.5 (2)	C1A—C2A—C3A—C4A	0.0 (3)
C6—C1—C2—C3	0.5 (3)	C1A—C2A—C3A—C9A	−179.58 (18)
C1—C2—C3—C9	176.48 (19)	C4A—C3A—C9A—C10A	23.3 (2)
C1—C2—C3—C4	−1.2 (3)	C4A—C3A—C9A—C12A	−154.9 (2)
C2—C3—C4—C5	1.4 (3)	C2A—C3A—C4A—C5A	−0.4 (3)
C9—C3—C4—C5	−176.34 (19)	C9A—C3A—C4A—C5A	179.20 (18)
C2—C3—C9—C10	155.86 (19)	C2A—C3A—C9A—C10A	−157.18 (18)
C2—C3—C9—C12	−28.1 (3)	C2A—C3A—C9A—C12A	24.6 (3)
C4—C3—C9—C10	−26.5 (3)	C3A—C4A—C5A—C6A	0.9 (3)
C4—C3—C9—C12	149.5 (2)	C4A—C5A—C6A—C1A	−1.0 (3)
C3—C4—C5—C6	−0.8 (3)	C4A—C5A—C6A—O7A	177.47 (19)
C4—C5—C6—C1	0.1 (3)	C3A—C9A—C12A—C13A	178.0 (2)
C4—C5—C6—O7	−178.49 (19)	C10A—C9A—C12A—C13A	−0.1 (3)
C3—C9—C12—C13	−176.44 (19)	C9A—C12A—C13A—C14A	−155.4 (2)
C10—C9—C12—C13	−0.6 (4)	C9A—C12A—C13A—C18A	23.7 (4)
C9—C12—C13—C18	−24.8 (3)	C14A—C13A—C18A—C17A	2.2 (3)
C9—C12—C13—C14	154.1 (2)	C12A—C13A—C14A—C15A	176.4 (2)
C18—C13—C14—C15	1.9 (3)	C18A—C13A—C14A—C15A	−2.8 (3)
C12—C13—C18—C17	177.28 (19)	C12A—C13A—C18A—C17A	−176.9 (2)
C14—C13—C18—C17	−1.6 (3)	C13A—C14A—C15A—C16A	1.4 (3)
C12—C13—C14—C15	−177.05 (19)	C14A—C15A—C16A—C17A	0.6 (3)
C13—C14—C15—C16	−1.1 (3)	C15A—C16A—C17A—C18A	−1.2 (3)
C14—C15—C16—C17	−0.1 (3)	C16A—C17A—C18A—C13A	−0.2 (3)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y+1, −z; (iii) x, y−1, z; (iv) x, y−1, z−1; (v) x, y, z+1; (vi) −x+1, −y+1, −z+1; (vii) −x+1, −y+2, −z+1; (viii) x, y+1, z; (ix) −x+1, −y+1, −z; (x) x, y, z−1; (xi) x, y+1, z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O7A	0.93	2.55	3.427 (5)	157
C14A—H14A···O7^viii	0.93	2.57	3.453 (5)	158

Symmetry code: (viii) x, y+1, z.