Di­methyl 5,5-di­cyano-2-hydroxy-4,6-di­phenyl­cyclo­hex-1-ene-1,3-di­carboxyl­ate

In the title mol­ecule, C₂₄H₂₀N₂O₅, the cyclo­hexene ring adopts a half-chair conformation. The molecular structure shows some intra- and intermolecular hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.037
• wR factor = 0.096
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.30 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C12    -   C13     ..       5.43 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C12    -   C14     ..       5.74 su
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C7     ..  O3      ..      97.00 Deg.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Dimethyl 5,5-dicyano-2-hydroxy-4,6-diphenylcyclohex-1-ene-1,3-dicarboxylate

Crystal data

C24H20N2O5	Z = 2
Mr = 416.42	F(000) = 436
Triclinic, P1	Dx = 1.280 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8185 (10) Å	Cell parameters from 6497 reflections
b = 10.9462 (13) Å	θ = 1.7–28.4°
c = 12.8297 (14) Å	µ = 0.09 mm^−1
α = 97.514 (9)°	T = 293 K
β = 106.713 (9)°	Shapeless, colorless
γ = 109.678 (9)°	0.46 × 0.37 × 0.25 mm
V = 1080.7 (2) Å^3

Data collection

STOE IPDS-II diffractometer	4138 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2631 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.033
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 1.7°
rotation method scans	h = −10→10
Absorption correction: integration STOE X-RED (Stoe & Cie, 2002)	k = −13→13
Tmin = 0.967, Tmax = 0.985	l = −15→15
9110 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 0.89	w = 1/[σ^2(Fo^2) + (0.0552P)^2] where P = (Fo^2 + 2Fc^2)/3
4138 reflections	(Δ/σ)max = 0.001
292 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su'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
O1	0.37131 (14)	0.98541 (10)	0.37191 (9)	0.0523 (4)
O2	0.20482 (15)	0.86721 (11)	0.48731 (10)	0.0600 (4)
O3	0.21127 (15)	0.66991 (11)	0.51146 (9)	0.0590 (4)
O4	0.32915 (16)	0.87024 (13)	0.10272 (10)	0.0707 (4)
O5	0.53385 (17)	1.07012 (11)	0.20268 (10)	0.0696 (5)
N1	0.6182 (2)	0.47735 (17)	0.28148 (17)	0.0874 (7)
N2	0.8151 (2)	0.84703 (16)	0.52467 (13)	0.0650 (5)
C1	0.2422 (2)	0.52626 (15)	0.29297 (13)	0.0485 (5)
C2	0.1169 (2)	0.53664 (18)	0.20596 (14)	0.0624 (6)
C3	−0.0211 (3)	0.4217 (2)	0.13383 (16)	0.0828 (8)
C4	−0.0335 (3)	0.2975 (2)	0.14942 (19)	0.0831 (8)
C5	0.0899 (3)	0.28665 (18)	0.23548 (19)	0.0777 (8)
C6	0.2263 (2)	0.39954 (16)	0.30703 (15)	0.0627 (6)
C7	0.39347 (19)	0.64841 (14)	0.37622 (13)	0.0447 (5)
C8	0.35183 (18)	0.77007 (14)	0.39715 (12)	0.0439 (5)
C9	0.40674 (18)	0.87635 (14)	0.35493 (12)	0.0424 (5)
C10	0.51978 (19)	0.88954 (14)	0.28522 (12)	0.0424 (5)
C11	0.53397 (19)	0.75746 (14)	0.24416 (12)	0.0426 (5)
C12	0.55798 (19)	0.68795 (14)	0.34270 (12)	0.0449 (5)
C13	0.5922 (2)	0.56870 (17)	0.30904 (14)	0.0562 (6)
C14	0.7067 (2)	0.77837 (16)	0.44400 (14)	0.0485 (5)
C15	0.66957 (19)	0.77439 (14)	0.19080 (12)	0.0450 (5)
C16	0.8356 (2)	0.87067 (17)	0.24196 (14)	0.0584 (6)
C17	0.9557 (2)	0.8815 (2)	0.19069 (16)	0.0697 (7)
C18	0.9117 (3)	0.7968 (2)	0.08795 (17)	0.0728 (7)
C19	0.7479 (3)	0.70213 (19)	0.03622 (15)	0.0682 (7)
C20	0.6266 (2)	0.69066 (16)	0.08623 (13)	0.0555 (5)
C21	0.24967 (19)	0.77500 (15)	0.46820 (12)	0.0481 (5)
C22	0.4486 (2)	0.94003 (16)	0.18561 (13)	0.0489 (5)
C23	0.1136 (3)	0.67059 (19)	0.58502 (16)	0.0715 (7)
C24	0.4644 (4)	1.1327 (2)	0.1183 (2)	0.0965 (10)
H1	0.31210	0.97700	0.41160	0.0780*
H2	0.12440	0.62060	0.19520	0.0750*
H3	−0.10540	0.42910	0.07480	0.0990*
H4	−0.12610	0.22090	0.10120	0.1000*
H5	0.08190	0.20250	0.24590	0.0930*
H6	0.30950	0.39100	0.36600	0.0750*
H7	0.4249 (18)	0.6256 (14)	0.4473 (13)	0.045 (4)*
H10	0.6314 (19)	0.9550 (14)	0.3317 (12)	0.044 (4)*
H11	0.421 (2)	0.6985 (14)	0.1859 (12)	0.046 (4)*
H16	0.86660	0.92850	0.31140	0.0700*
H17	1.06700	0.94660	0.22580	0.0840*
H18	0.99320	0.80400	0.05390	0.0870*
H19	0.71790	0.64490	−0.03330	0.0820*
H20	0.51510	0.62640	0.04980	0.0670*
H23A	0.09260	0.59060	0.61160	0.1070*
H23B	0.00570	0.67390	0.54430	0.1070*
H23C	0.17790	0.74770	0.64790	0.1070*
H24A	0.53590	1.22670	0.13880	0.1450*
H24B	0.34960	1.12110	0.11380	0.1450*
H24C	0.46180	1.09170	0.04660	0.1450*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0620 (7)	0.0521 (6)	0.0552 (6)	0.0325 (5)	0.0266 (5)	0.0137 (5)
O2	0.0674 (7)	0.0639 (7)	0.0658 (7)	0.0357 (6)	0.0362 (6)	0.0161 (6)
O3	0.0679 (7)	0.0605 (7)	0.0626 (7)	0.0262 (6)	0.0397 (6)	0.0207 (6)
O4	0.0695 (8)	0.0761 (8)	0.0529 (7)	0.0257 (7)	0.0048 (7)	0.0188 (6)
O5	0.0866 (9)	0.0527 (7)	0.0702 (8)	0.0284 (6)	0.0225 (7)	0.0275 (6)
N1	0.1041 (13)	0.0679 (10)	0.1159 (15)	0.0522 (10)	0.0535 (12)	0.0238 (10)
N2	0.0602 (9)	0.0715 (9)	0.0561 (9)	0.0277 (8)	0.0099 (8)	0.0125 (8)
C1	0.0531 (9)	0.0482 (9)	0.0462 (9)	0.0170 (7)	0.0249 (8)	0.0095 (7)
C2	0.0556 (10)	0.0655 (11)	0.0560 (10)	0.0155 (9)	0.0168 (9)	0.0128 (8)
C3	0.0641 (12)	0.0994 (17)	0.0580 (11)	0.0107 (12)	0.0146 (10)	0.0071 (11)
C4	0.0791 (14)	0.0731 (14)	0.0655 (13)	−0.0077 (11)	0.0372 (12)	−0.0087 (10)
C5	0.0934 (15)	0.0517 (11)	0.0797 (14)	0.0095 (10)	0.0467 (13)	0.0055 (10)
C6	0.0729 (11)	0.0484 (10)	0.0653 (11)	0.0168 (8)	0.0316 (9)	0.0129 (8)
C7	0.0499 (9)	0.0461 (8)	0.0418 (8)	0.0210 (7)	0.0184 (7)	0.0128 (7)
C8	0.0456 (8)	0.0461 (8)	0.0412 (8)	0.0193 (7)	0.0171 (7)	0.0081 (6)
C9	0.0430 (8)	0.0439 (8)	0.0394 (8)	0.0205 (7)	0.0119 (6)	0.0047 (6)
C10	0.0426 (8)	0.0434 (8)	0.0397 (8)	0.0171 (7)	0.0134 (7)	0.0085 (6)
C11	0.0424 (8)	0.0447 (8)	0.0397 (8)	0.0181 (7)	0.0140 (7)	0.0066 (6)
C12	0.0482 (8)	0.0449 (8)	0.0450 (8)	0.0231 (7)	0.0168 (7)	0.0094 (6)
C13	0.0620 (10)	0.0538 (10)	0.0647 (10)	0.0303 (8)	0.0290 (9)	0.0181 (8)
C14	0.0506 (9)	0.0534 (9)	0.0492 (9)	0.0282 (8)	0.0176 (8)	0.0173 (8)
C15	0.0465 (8)	0.0489 (8)	0.0440 (8)	0.0224 (7)	0.0183 (7)	0.0112 (7)
C16	0.0494 (9)	0.0688 (11)	0.0522 (9)	0.0198 (8)	0.0187 (8)	0.0080 (8)
C17	0.0481 (10)	0.0888 (13)	0.0723 (12)	0.0227 (9)	0.0262 (9)	0.0215 (10)
C18	0.0686 (12)	0.0982 (14)	0.0751 (12)	0.0434 (11)	0.0432 (11)	0.0288 (11)
C19	0.0803 (13)	0.0778 (12)	0.0594 (10)	0.0381 (11)	0.0377 (10)	0.0112 (9)
C20	0.0602 (10)	0.0543 (9)	0.0522 (9)	0.0219 (8)	0.0241 (8)	0.0062 (7)
C21	0.0478 (9)	0.0515 (9)	0.0452 (8)	0.0191 (7)	0.0183 (7)	0.0100 (7)
C22	0.0521 (9)	0.0551 (10)	0.0482 (9)	0.0259 (8)	0.0233 (8)	0.0158 (7)
C23	0.0784 (13)	0.0780 (12)	0.0762 (12)	0.0302 (10)	0.0513 (11)	0.0254 (10)
C24	0.140 (2)	0.0817 (14)	0.0948 (16)	0.0623 (15)	0.0442 (16)	0.0532 (13)

Geometric parameters (Å, º)

O1—C9	1.339 (2)	C12—C14	1.483 (2)
O2—C21	1.223 (2)	C15—C20	1.391 (2)
O3—C21	1.326 (2)	C15—C16	1.383 (2)
O3—C23	1.450 (3)	C16—C17	1.380 (3)
O4—C22	1.194 (2)	C17—C18	1.375 (3)
O5—C22	1.321 (2)	C18—C19	1.364 (3)
O5—C24	1.453 (3)	C19—C20	1.377 (3)
O1—H1	0.8205	C2—H2	0.9304
N1—C13	1.134 (3)	C3—H3	0.9303
N2—C14	1.137 (2)	C4—H4	0.9302
C1—C2	1.374 (2)	C5—H5	0.9302
C1—C6	1.388 (2)	C6—H6	0.9300
C1—C7	1.521 (2)	C7—H7	0.965 (15)
C2—C3	1.392 (3)	C10—H10	0.956 (16)
C3—C4	1.373 (3)	C11—H11	0.990 (16)
C4—C5	1.359 (3)	C16—H16	0.9301
C5—C6	1.373 (3)	C17—H17	0.9299
C7—C8	1.508 (2)	C18—H18	0.9301
C7—C12	1.569 (2)	C19—H19	0.9298
C8—C21	1.462 (2)	C20—H20	0.9295
C8—C9	1.348 (2)	C23—H23A	0.9604
C9—C10	1.505 (2)	C23—H23B	0.9601
C10—C11	1.531 (2)	C23—H23C	0.9598
C10—C22	1.513 (2)	C24—H24A	0.9604
C11—C15	1.513 (2)	C24—H24B	0.9603
C11—C12	1.558 (2)	C24—H24C	0.9597
C12—C13	1.475 (2)
O1···O2	2.5482 (17)	C24···C19^viii	3.433 (4)
O1···O5	3.0083 (18)	C24···C20^viii	3.526 (3)
O1···C9^i	3.3280 (18)	C1···H11	2.802 (16)
O1···N2^i	3.237 (2)	C2···H11	2.777 (18)
O1···C8^i	3.3568 (19)	C4···H18^ix	2.8647
O1···C21^i	3.317 (2)	C5···H23C^vii	3.0884
O2···N2^i	3.212 (2)	C8···H2	2.6655
O2···O1	2.5482 (17)	C8···H11	3.008 (16)
O2···C10^i	3.3228 (19)	C9···H2	3.0177
O3···C1	3.159 (2)	C9···H1^i	3.0801
O4···C4^ii	3.317 (3)	C10···H16	2.8534
O5···O1	3.0083 (18)	C13···H6	2.9473
O1···H17^iii	2.6508	C14···H16	2.8519
O2···H23B	2.5954	C14···H10	2.702 (15)
O2···H23C	2.6057	C16···H10	2.730 (18)
O2···H1	1.8306	C19···H24B^viii	3.0546
O2···H10^i	2.502 (15)	C21···H1	2.3557
O3···H7	2.422 (17)	H1···O2	1.8306
O4···H24B	2.6726	H1···C21	2.3557
O4···H11	2.526 (16)	H1···N2^i	2.6847
O4···H18^iii	2.6575	H1···C9^i	3.0801
O4···H4^ii	2.5429	H2···C8	2.6655
O4···H24C	2.6066	H2···C9	3.0177
O5···H23C^i	2.6262	H2···H11	2.5073
N1···C6	3.394 (3)	H4···O4^ii	2.5429
N2···O1^i	3.237 (2)	H6···C13	2.9473
N2···O2^i	3.212 (2)	H6···H7	2.3764
N1···H24A^iv	2.8261	H7···O3	2.422 (17)
N1···H23A^v	2.9105	H7···H6	2.3764
N2···H23B^vi	2.9166	H10···C14	2.702 (15)
N2···H1^i	2.6847	H10···C16	2.730 (18)
C1···O3	3.159 (2)	H10···H16	2.2694
C2···C21	3.589 (2)	H10···O2^i	2.502 (14)
C2···C9	3.598 (2)	H11···O4	2.526 (16)
C2···C11	3.504 (3)	H11···C1	2.802 (16)
C4···O4^ii	3.317 (3)	H11···C2	2.777 (18)
C5···C23^vii	3.377 (4)	H11···C8	3.008 (16)
C6···C23^vii	3.551 (3)	H11···H2	2.5073
C6···N1	3.394 (3)	H11···H20	2.2966
C6···C13	3.124 (3)	H16···C10	2.8534
C8···O1^i	3.3568 (19)	H16···C14	2.8519
C9···O1^i	3.3280 (18)	H16···H10	2.2694
C9···C2	3.598 (2)	H17···O1^vi	2.6508
C9···C14	3.154 (3)	H18···O4^vi	2.6575
C10···O2^i	3.3228 (19)	H18···C4^ix	2.8647
C11···C2	3.504 (3)	H20···H11	2.2966
C13···C6	3.124 (3)	H23A···N1^v	2.9105
C13···C20	3.357 (2)	H23B···O2	2.5954
C14···C16	3.262 (3)	H23B···N2^iii	2.9166
C14···C9	3.154 (3)	H23C···O2	2.6057
C16···C14	3.262 (3)	H23C···O5^i	2.6262
C19···C24^viii	3.433 (4)	H23C···C5^vii	3.0884
C20···C13	3.357 (2)	H24A···N1^x	2.8261
C20···C24^viii	3.526 (3)	H24B···O4	2.6726
C21···O1^i	3.317 (2)	H24B···C19^viii	3.0546
C21···C2	3.589 (2)	H24C···O4	2.6066
C23···C6^vii	3.551 (3)	H24C···H24C^viii	2.5808
C23···C5^vii	3.377 (4)
C21—O3—C23	116.06 (14)	O4—C22—C10	123.71 (16)
C22—O5—C24	116.39 (15)	O5—C22—C10	111.56 (14)
C9—O1—H1	109.46	O4—C22—O5	124.72 (16)
C2—C1—C7	122.43 (15)	C1—C2—H2	119.96
C6—C1—C7	119.11 (15)	C3—C2—H2	119.96
C2—C1—C6	118.43 (16)	C2—C3—H3	119.84
C1—C2—C3	120.08 (18)	C4—C3—H3	119.85
C2—C3—C4	120.3 (2)	C3—C4—H4	120.10
C3—C4—C5	119.9 (2)	C5—C4—H4	120.05
C4—C5—C6	120.17 (19)	C4—C5—H5	119.92
C1—C6—C5	121.15 (18)	C6—C5—H5	119.91
C1—C7—C12	113.23 (13)	C1—C6—H6	119.40
C8—C7—C12	108.91 (12)	C5—C6—H6	119.45
C1—C7—C8	113.69 (14)	C1—C7—H7	107.4 (9)
C7—C8—C21	118.84 (13)	C8—C7—H7	106.8 (10)
C9—C8—C21	117.99 (15)	C12—C7—H7	106.4 (10)
C7—C8—C9	123.16 (15)	C9—C10—H10	106.9 (10)
O1—C9—C10	111.15 (13)	C11—C10—H10	109.5 (10)
C8—C9—C10	124.44 (15)	C22—C10—H10	109.0 (9)
O1—C9—C8	124.40 (15)	C10—C11—H11	106.7 (10)
C9—C10—C22	108.85 (14)	C12—C11—H11	106.3 (9)
C11—C10—C22	109.83 (12)	C15—C11—H11	107.7 (10)
C9—C10—C11	112.74 (13)	C15—C16—H16	119.80
C10—C11—C15	113.03 (13)	C17—C16—H16	119.76
C12—C11—C15	113.82 (14)	C16—C17—H17	119.76
C10—C11—C12	108.80 (12)	C18—C17—H17	119.82
C7—C12—C13	110.78 (13)	C17—C18—H18	120.17
C7—C12—C14	107.50 (13)	C19—C18—H18	120.15
C11—C12—C13	109.60 (13)	C18—C19—H19	119.78
C11—C12—C14	111.40 (13)	C20—C19—H19	119.73
C13—C12—C14	107.40 (15)	C15—C20—H20	119.74
C7—C12—C11	110.11 (14)	C19—C20—H20	119.70
N1—C13—C12	178.89 (19)	O3—C23—H23A	109.45
N2—C14—C12	176.5 (2)	O3—C23—H23B	109.49
C11—C15—C20	119.16 (15)	O3—C23—H23C	109.46
C16—C15—C20	118.40 (16)	H23A—C23—H23B	109.50
C11—C15—C16	122.44 (14)	H23A—C23—H23C	109.46
C15—C16—C17	120.44 (16)	H23B—C23—H23C	109.47
C16—C17—C18	120.4 (2)	O5—C24—H24A	109.48
C17—C18—C19	119.7 (2)	O5—C24—H24B	109.45
C18—C19—C20	120.49 (18)	O5—C24—H24C	109.47
C15—C20—C19	120.57 (17)	H24A—C24—H24B	109.46
O2—C21—C8	123.73 (15)	H24A—C24—H24C	109.47
O3—C21—C8	113.46 (14)	H24B—C24—H24C	109.49
O2—C21—O3	122.81 (16)
C23—O3—C21—C8	178.54 (14)	C21—C8—C9—O1	−1.3 (2)
C23—O3—C21—O2	−0.8 (2)	C21—C8—C9—C10	176.94 (14)
C24—O5—C22—C10	−173.06 (19)	O1—C9—C10—C22	−46.43 (17)
C24—O5—C22—O4	6.3 (3)	C8—C9—C10—C22	135.11 (16)
C2—C1—C7—C8	31.1 (2)	C8—C9—C10—C11	13.0 (2)
C7—C1—C6—C5	178.54 (19)	O1—C9—C10—C11	−168.56 (13)
C6—C1—C7—C12	88.25 (19)	C9—C10—C22—O5	99.93 (17)
C6—C1—C2—C3	−0.5 (3)	C11—C10—C22—O4	44.4 (2)
C6—C1—C7—C8	−146.76 (16)	C9—C10—C22—O4	−79.4 (2)
C2—C1—C6—C5	0.6 (3)	C9—C10—C11—C15	−170.46 (13)
C7—C1—C2—C3	−178.40 (19)	C22—C10—C11—C12	−164.57 (14)
C2—C1—C7—C12	−93.9 (2)	C22—C10—C11—C15	67.97 (18)
C1—C2—C3—C4	0.4 (3)	C9—C10—C11—C12	−42.99 (18)
C2—C3—C4—C5	−0.2 (4)	C11—C10—C22—O5	−136.20 (16)
C3—C4—C5—C6	0.3 (4)	C15—C11—C12—C13	−46.41 (18)
C4—C5—C6—C1	−0.5 (4)	C10—C11—C12—C14	−54.71 (19)
C12—C7—C8—C21	−157.20 (13)	C15—C11—C12—C7	−168.52 (12)
C8—C7—C12—C14	69.31 (16)	C12—C11—C15—C16	−75.25 (19)
C8—C7—C12—C11	−52.22 (15)	C12—C11—C15—C20	104.94 (16)
C8—C7—C12—C13	−173.62 (13)	C10—C11—C12—C13	−173.43 (14)
C12—C7—C8—C9	21.7 (2)	C10—C11—C15—C20	−130.28 (15)
C1—C7—C12—C14	−163.16 (13)	C10—C11—C15—C16	49.5 (2)
C1—C7—C12—C13	−46.09 (18)	C10—C11—C12—C7	64.47 (16)
C1—C7—C8—C21	75.53 (18)	C15—C11—C12—C14	72.31 (17)
C1—C7—C12—C11	75.32 (16)	C20—C15—C16—C17	−0.9 (3)
C1—C7—C8—C9	−105.61 (18)	C16—C15—C20—C19	1.2 (3)
C7—C8—C9—O1	179.81 (14)	C11—C15—C16—C17	179.27 (16)
C7—C8—C21—O2	−177.67 (15)	C11—C15—C20—C19	−178.97 (16)
C7—C8—C9—C10	−1.9 (2)	C15—C16—C17—C18	0.1 (3)
C9—C8—C21—O2	3.4 (2)	C16—C17—C18—C19	0.4 (3)
C9—C8—C21—O3	−175.90 (14)	C17—C18—C19—C20	−0.1 (3)
C7—C8—C21—O3	3.0 (2)	C18—C19—C20—C15	−0.7 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.83	2.548 (2)	145
C4—H4···O4^ii	0.93	2.54	3.317 (3)	141
C7—H7···O3	0.96 (2)	2.42 (2)	2.720 (2)	97 (1)
C10—H10···O2^i	0.96 (2)	2.50 (1)	3.323 (2)	144 (1)
C11—H11···O4	0.99 (2)	2.53 (2)	2.878 (2)	101 (1)

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