Swietenine

The crystal structure of swietenine, C₃₂H₄₀O₉, from Swietenia macrophylla, a plant belonging to the meliaceae family, is reported. The crystal structure is stabilized by C—H...O hydrogen bonds. A comparison of structural features with a de-tigloyl­ated iodo­benzene derivative shows that the overall conformation is not affected by substitution of the (1-methyl­propyl)­carbonyl­oxy side chain.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.047
• wR factor = 0.132
• Data-to-parameter ratio = 8.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.88 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.62 Ratio
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C24
PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ......        C27
PLAT410_ALERT_2_C Short Intra H...H Contact  H15A   ..  H30      =       1.95 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.02
           From the CIF: _reflns_number_total               3243
           Count of symmetry unique reflns         3245
           Completeness (_total/calc)             99.94%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

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

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

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 and PARST97 (Nardelli, 1995).

swietenine

Crystal data

C32H40O9	Dx = 1.293 Mg m^−3
Mr = 568.64	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 5750 reflections
a = 9.866 (3) Å	θ = 1.7–26.0°
b = 16.092 (5) Å	µ = 0.09 mm^−1
c = 18.392 (5) Å	T = 293 K
V = 2920.1 (14) Å^3	Prism, colourless
Z = 4	0.20 × 0.20 × 0.20 mm
F(000) = 1216

Data collection

Bruker SMART CCD area-detector diffractometer	2916 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 26.0°, θmin = 1.7°
ω scans	h = −12→11
22610 measured reflections	k = −19→19
3243 independent reflections	l = −22→22

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.132	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0894P)^2 + 0.282P] where P = (Fo^2 + 2Fc^2)/3
3243 reflections	(Δ/σ)max = 0.002
371 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

Special details

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
C1	0.5337 (3)	−0.03537 (19)	−0.02650 (13)	0.0441 (6)
C2	0.5946 (3)	0.04724 (17)	−0.00644 (14)	0.0446 (7)
H2	0.5939	0.0831	−0.0495	0.054*
C3	0.7433 (3)	0.03610 (17)	0.01899 (14)	0.0441 (6)
H3	0.8043	0.0529	−0.0204	0.053*
C4	0.7762 (3)	−0.05403 (17)	0.04130 (13)	0.0379 (6)
C5	0.6532 (3)	−0.08533 (14)	0.08643 (12)	0.0312 (5)
H5	0.6349	−0.0408	0.1214	0.037*
C6	0.6802 (3)	−0.16302 (15)	0.13335 (14)	0.0394 (6)
H6	0.5916	−0.1852	0.1476	0.047*
C7	0.7577 (3)	−0.14505 (17)	0.20308 (14)	0.0445 (6)
C8	0.4098 (3)	0.04169 (16)	0.08738 (13)	0.0377 (6)
C9	0.3968 (3)	−0.05205 (17)	0.08052 (14)	0.0376 (6)
H9	0.3170	−0.0620	0.0500	0.045*
C10	0.5203 (3)	−0.09202 (16)	0.03918 (13)	0.0360 (6)
C11	0.3671 (3)	−0.09357 (16)	0.15364 (14)	0.0406 (6)
H11A	0.3443	−0.1515	0.1455	0.049*
H11B	0.4480	−0.0918	0.1836	0.049*
C12	0.2512 (3)	−0.05153 (18)	0.19402 (15)	0.0441 (6)
H12A	0.2394	−0.0785	0.2408	0.053*
H12B	0.1682	−0.0591	0.1665	0.053*
C13	0.2737 (3)	0.04155 (17)	0.20640 (13)	0.0401 (6)
C14	0.2987 (3)	0.08374 (18)	0.13250 (14)	0.0459 (7)
H14	0.2145	0.0783	0.1047	0.055*
C15	0.3200 (4)	0.1771 (2)	0.14540 (17)	0.0584 (9)
H15A	0.3553	0.2015	0.1011	0.070*
H15B	0.2324	0.2023	0.1547	0.070*
C16	0.4127 (4)	0.19899 (19)	0.20627 (18)	0.0563 (8)
C17	0.3999 (3)	0.05596 (16)	0.25376 (14)	0.0399 (6)
H17	0.4767	0.0285	0.2300	0.048*
C18	0.1462 (3)	0.0770 (2)	0.24371 (17)	0.0562 (8)
H18A	0.1581	0.1355	0.2520	0.084*
H18B	0.1324	0.0494	0.2894	0.084*
H18C	0.0687	0.0683	0.2130	0.084*
C19	0.4851 (4)	−0.18062 (19)	0.01481 (18)	0.0550 (8)
H19A	0.4769	−0.2158	0.0567	0.082*
H19B	0.5556	−0.2014	−0.0163	0.082*
H19C	0.4008	−0.1801	−0.0113	0.082*
C20	0.3900 (3)	0.02306 (18)	0.32943 (14)	0.0412 (6)
C21	0.3526 (3)	0.0644 (2)	0.38998 (15)	0.0537 (8)
H21	0.3307	0.1206	0.3913	0.064*
C22	0.4175 (4)	−0.0594 (2)	0.35288 (17)	0.0569 (8)
H22	0.4479	−0.1033	0.3243	0.068*
C23	0.3911 (4)	−0.0616 (2)	0.42404 (19)	0.0679 (10)
H23	0.3992	−0.1088	0.4530	0.081*
C24	0.8123 (4)	0.16455 (19)	0.07162 (17)	0.0531 (8)
C25	0.8406 (4)	0.20876 (19)	0.14109 (19)	0.0552 (8)
C26	0.8040 (4)	0.1741 (2)	0.20399 (19)	0.0635 (9)
H26	0.7616	0.1226	0.2012	0.076*
C27	0.8238 (6)	0.2092 (3)	0.2786 (2)	0.0896 (14)
H27A	0.7880	0.1712	0.3140	0.134*
H27B	0.7774	0.2615	0.2823	0.134*
H27C	0.9188	0.2175	0.2874	0.134*
C28	0.8051 (3)	−0.1047 (2)	−0.02888 (15)	0.0501 (7)
H28A	0.8260	−0.1612	−0.0161	0.075*
H28B	0.8806	−0.0807	−0.0542	0.075*
H28C	0.7266	−0.1037	−0.0597	0.075*
C29	0.9082 (3)	−0.0538 (2)	0.08621 (17)	0.0526 (7)
H29A	0.9299	−0.1095	0.1006	0.079*
H29B	0.8961	−0.0200	0.1287	0.079*
H29C	0.9806	−0.0316	0.0573	0.079*
C30	0.5014 (3)	0.08449 (18)	0.05023 (15)	0.0472 (7)
H30	0.5088	0.1411	0.0596	0.057*
C31	0.7735 (5)	−0.0610 (3)	0.30757 (18)	0.0783 (12)
H31A	0.7333	−0.0119	0.3280	0.117*
H31B	0.8690	−0.0523	0.3012	0.117*
H31C	0.7591	−0.1071	0.3398	0.117*
C32	0.9119 (6)	0.2903 (2)	0.1326 (3)	0.0864 (13)
H32A	0.9263	0.3014	0.0819	0.130*
H32B	0.9977	0.2882	0.1571	0.130*
H32C	0.8575	0.3337	0.1533	0.130*
O1	0.4323 (2)	0.14448 (12)	0.26057 (12)	0.0558 (6)
O2	0.7682 (3)	0.08780 (13)	0.08164 (11)	0.0550 (6)
O3	0.7117 (2)	−0.07862 (12)	0.23777 (9)	0.0486 (5)
O4	0.8246 (5)	0.19404 (18)	0.01261 (15)	0.1114 (15)
O5	0.8468 (3)	−0.18937 (16)	0.22468 (13)	0.0666 (7)
O6	0.3512 (3)	0.01348 (18)	0.44850 (11)	0.0675 (7)
O7	0.7485 (3)	−0.22715 (13)	0.09531 (12)	0.0556 (6)
H7	0.8110	−0.2448	0.1203	0.083*
O8	0.4638 (4)	0.26602 (15)	0.21314 (16)	0.0834 (9)
O9	0.4902 (3)	−0.05080 (17)	−0.08602 (10)	0.0664 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0394 (14)	0.0683 (18)	0.0245 (11)	0.0086 (13)	−0.0008 (11)	−0.0045 (12)
C2	0.0591 (17)	0.0468 (14)	0.0278 (12)	0.0062 (14)	0.0053 (12)	0.0100 (11)
C3	0.0566 (17)	0.0488 (14)	0.0267 (11)	−0.0067 (13)	0.0081 (12)	0.0001 (11)
C4	0.0366 (13)	0.0476 (14)	0.0296 (12)	−0.0023 (12)	0.0014 (10)	−0.0020 (10)
C5	0.0356 (12)	0.0324 (11)	0.0257 (10)	0.0008 (10)	−0.0005 (10)	−0.0048 (9)
C6	0.0479 (15)	0.0334 (12)	0.0368 (12)	0.0034 (11)	0.0011 (12)	−0.0021 (10)
C7	0.0467 (15)	0.0481 (15)	0.0386 (13)	0.0025 (13)	−0.0038 (12)	0.0109 (12)
C8	0.0438 (14)	0.0437 (13)	0.0257 (11)	0.0073 (12)	−0.0026 (10)	−0.0011 (10)
C9	0.0351 (12)	0.0472 (14)	0.0303 (12)	−0.0028 (12)	−0.0055 (10)	−0.0080 (11)
C10	0.0366 (13)	0.0409 (13)	0.0305 (12)	−0.0035 (11)	−0.0050 (10)	−0.0076 (10)
C11	0.0453 (15)	0.0375 (12)	0.0389 (13)	−0.0054 (12)	0.0000 (11)	−0.0033 (11)
C12	0.0375 (14)	0.0564 (16)	0.0385 (13)	−0.0067 (12)	0.0021 (11)	−0.0031 (12)
C13	0.0388 (13)	0.0499 (14)	0.0315 (12)	0.0051 (12)	0.0020 (11)	0.0001 (11)
C14	0.0489 (16)	0.0539 (16)	0.0348 (13)	0.0128 (14)	−0.0008 (12)	0.0018 (12)
C15	0.077 (2)	0.0490 (17)	0.0487 (17)	0.0192 (16)	0.0137 (17)	0.0086 (14)
C16	0.073 (2)	0.0405 (15)	0.0553 (18)	0.0041 (15)	0.0274 (17)	−0.0012 (13)
C17	0.0383 (13)	0.0424 (13)	0.0390 (13)	−0.0017 (12)	0.0068 (11)	−0.0053 (11)
C18	0.0424 (16)	0.079 (2)	0.0474 (16)	0.0132 (16)	0.0050 (13)	−0.0035 (15)
C19	0.0572 (18)	0.0542 (17)	0.0534 (16)	−0.0080 (15)	−0.0041 (15)	−0.0236 (14)
C20	0.0328 (13)	0.0541 (15)	0.0367 (13)	0.0007 (12)	−0.0006 (11)	−0.0041 (11)
C21	0.0544 (18)	0.0683 (19)	0.0384 (14)	0.0124 (16)	−0.0031 (13)	−0.0072 (13)
C22	0.072 (2)	0.0524 (17)	0.0464 (16)	0.0050 (16)	0.0001 (15)	0.0007 (13)
C23	0.076 (2)	0.076 (2)	0.0523 (18)	0.000 (2)	−0.0095 (18)	0.0167 (17)
C24	0.062 (2)	0.0443 (15)	0.0531 (17)	−0.0070 (14)	0.0030 (15)	0.0072 (13)
C25	0.0562 (18)	0.0431 (15)	0.0663 (19)	−0.0022 (14)	−0.0031 (17)	−0.0052 (14)
C26	0.072 (2)	0.0578 (19)	0.0606 (19)	−0.0047 (18)	0.0058 (18)	−0.0124 (16)
C27	0.107 (4)	0.086 (3)	0.076 (3)	−0.001 (3)	0.007 (3)	−0.032 (2)
C28	0.0507 (17)	0.0596 (17)	0.0401 (14)	0.0075 (14)	0.0086 (13)	−0.0072 (13)
C29	0.0414 (15)	0.071 (2)	0.0457 (15)	−0.0090 (15)	−0.0033 (13)	0.0070 (15)
C30	0.0627 (19)	0.0415 (14)	0.0373 (13)	0.0094 (13)	0.0084 (13)	0.0047 (11)
C31	0.095 (3)	0.099 (3)	0.0410 (16)	−0.001 (3)	−0.0233 (19)	−0.0115 (18)
C32	0.103 (3)	0.054 (2)	0.102 (3)	−0.020 (2)	−0.018 (3)	−0.002 (2)
O1	0.0683 (14)	0.0457 (11)	0.0533 (12)	−0.0091 (10)	0.0015 (11)	−0.0074 (9)
O2	0.0791 (16)	0.0469 (11)	0.0390 (10)	−0.0187 (11)	0.0077 (11)	−0.0026 (9)
O3	0.0594 (12)	0.0560 (11)	0.0303 (9)	0.0054 (10)	−0.0101 (9)	−0.0034 (8)
O4	0.207 (5)	0.0634 (15)	0.0636 (16)	−0.049 (2)	0.009 (2)	0.0137 (13)
O5	0.0659 (15)	0.0735 (14)	0.0605 (13)	0.0208 (13)	−0.0147 (12)	0.0104 (12)
O6	0.0698 (16)	0.0986 (19)	0.0339 (10)	0.0142 (15)	0.0006 (11)	−0.0016 (11)
O7	0.0688 (15)	0.0424 (10)	0.0555 (12)	0.0164 (10)	0.0041 (12)	−0.0073 (9)
O8	0.112 (2)	0.0469 (13)	0.0914 (19)	−0.0160 (14)	0.0294 (19)	−0.0041 (13)
O9	0.0636 (15)	0.1070 (19)	0.0285 (9)	0.0038 (14)	−0.0113 (10)	−0.0090 (11)

Geometric parameters (Å, º)

C1—O9	1.201 (3)	C17—O1	1.465 (3)
C1—C2	1.505 (4)	C17—C20	1.492 (4)
C1—C10	1.519 (4)	C17—H17	0.9800
C2—C30	1.514 (4)	C18—H18A	0.9600
C2—C3	1.550 (5)	C18—H18B	0.9600
C2—H2	0.9800	C18—H18C	0.9600
C3—O2	1.442 (3)	C19—H19A	0.9600
C3—C4	1.542 (4)	C19—H19B	0.9600
C3—H3	0.9800	C19—H19C	0.9600
C4—C29	1.542 (4)	C20—C21	1.349 (4)
C4—C28	1.553 (3)	C20—C22	1.422 (4)
C4—C5	1.554 (4)	C21—O6	1.353 (4)
C5—C6	1.542 (3)	C21—H21	0.9300
C5—C10	1.577 (3)	C22—C23	1.335 (5)
C5—H5	0.9800	C22—H22	0.9300
C6—O7	1.418 (3)	C23—O6	1.348 (5)
C6—C7	1.521 (4)	C23—H23	0.9300
C6—H6	0.9800	C24—O4	1.191 (4)
C7—O5	1.200 (4)	C24—O2	1.323 (4)
C7—O3	1.325 (3)	C24—C25	1.489 (5)
C8—C30	1.326 (4)	C25—C26	1.334 (5)
C8—C9	1.519 (4)	C25—C32	1.497 (5)
C8—C14	1.532 (4)	C26—C27	1.497 (5)
C9—C11	1.530 (4)	C26—H26	0.9300
C9—C10	1.574 (4)	C27—H27A	0.9600
C9—H9	0.9800	C27—H27B	0.9600
C10—C19	1.534 (4)	C27—H27C	0.9600
C11—C12	1.522 (4)	C28—H28A	0.9600
C11—H11A	0.9700	C28—H28B	0.9600
C11—H11B	0.9700	C28—H28C	0.9600
C12—C13	1.531 (4)	C29—H29A	0.9600
C12—H12A	0.9700	C29—H29B	0.9600
C12—H12B	0.9700	C29—H29C	0.9600
C13—C18	1.542 (4)	C30—H30	0.9300
C13—C17	1.537 (4)	C31—O3	1.449 (4)
C13—C14	1.539 (4)	C31—H31A	0.9600
C14—C15	1.535 (4)	C31—H31B	0.9600
C14—H14	0.9800	C31—H31C	0.9600
C15—C16	1.488 (5)	C32—H32A	0.9600
C15—H15A	0.9700	C32—H32B	0.9600
C15—H15B	0.9700	C32—H32C	0.9600
C16—O8	1.198 (4)	O7—H7	0.8200
C16—O1	1.343 (4)
O9—C1—C2	123.3 (3)	O8—C16—O1	116.7 (4)
O9—C1—C10	124.7 (3)	O8—C16—C15	123.5 (3)
C2—C1—C10	111.7 (2)	O1—C16—C15	119.5 (3)
C1—C2—C30	106.0 (2)	O1—C17—C20	106.2 (2)
C1—C2—C3	110.5 (2)	O1—C17—C13	111.8 (2)
C30—C2—C3	114.4 (2)	C20—C17—C13	115.0 (2)
C1—C2—H2	108.6	O1—C17—H17	107.8
C30—C2—H2	108.6	C20—C17—H17	107.8
C3—C2—H2	108.6	C13—C17—H17	107.8
O2—C3—C4	107.1 (2)	C13—C18—H18A	109.5
O2—C3—C2	109.6 (2)	C13—C18—H18B	109.5
C4—C3—C2	112.8 (2)	H18A—C18—H18B	109.5
O2—C3—H3	109.1	C13—C18—H18C	109.5
C4—C3—H3	109.1	H18A—C18—H18C	109.5
C2—C3—H3	109.1	H18B—C18—H18C	109.5
C3—C4—C29	108.5 (2)	C10—C19—H19A	109.5
C3—C4—C28	108.2 (2)	C10—C19—H19B	109.5
C29—C4—C28	107.0 (2)	H19A—C19—H19B	109.5
C3—C4—C5	106.4 (2)	C10—C19—H19C	109.5
C29—C4—C5	112.0 (2)	H19A—C19—H19C	109.5
C28—C4—C5	114.6 (2)	H19B—C19—H19C	109.5
C6—C5—C4	115.3 (2)	C21—C20—C22	105.2 (3)
C6—C5—C10	113.3 (2)	C21—C20—C17	127.8 (3)
C4—C5—C10	112.14 (19)	C22—C20—C17	127.0 (3)
C6—C5—H5	104.9	O6—C21—C20	111.1 (3)
C4—C5—H5	104.9	O6—C21—H21	124.4
C10—C5—H5	104.9	C20—C21—H21	124.4
O7—C6—C7	108.4 (2)	C23—C22—C20	106.5 (3)
O7—C6—C5	113.3 (2)	C23—C22—H22	126.7
C7—C6—C5	113.8 (2)	C20—C22—H22	126.7
O7—C6—H6	107.0	C22—C23—O6	111.1 (3)
C7—C6—H6	107.0	C22—C23—H23	124.4
C5—C6—H6	107.0	O6—C23—H23	124.4
O5—C7—O3	124.8 (3)	O4—C24—O2	122.2 (3)
O5—C7—C6	122.3 (3)	O4—C24—C25	124.9 (3)
O3—C7—C6	112.8 (2)	O2—C24—C25	112.9 (3)
C30—C8—C9	122.1 (2)	C26—C25—C24	119.6 (3)
C30—C8—C14	122.5 (2)	C26—C25—C32	125.7 (3)
C9—C8—C14	115.0 (2)	C24—C25—C32	114.7 (3)
C8—C9—C11	112.1 (2)	C25—C26—C27	127.0 (4)
C8—C9—C10	112.3 (2)	C25—C26—H26	116.5
C11—C9—C10	113.2 (2)	C27—C26—H26	116.5
C8—C9—H9	106.2	C26—C27—H27A	109.5
C11—C9—H9	106.2	C26—C27—H27B	109.5
C10—C9—H9	106.2	H27A—C27—H27B	109.5
C19—C10—C1	110.2 (2)	C26—C27—H27C	109.5
C19—C10—C9	110.2 (2)	H27A—C27—H27C	109.5
C1—C10—C9	101.9 (2)	H27B—C27—H27C	109.5
C19—C10—C5	114.4 (2)	C4—C28—H28A	109.5
C1—C10—C5	109.0 (2)	C4—C28—H28B	109.5
C9—C10—C5	110.48 (18)	H28A—C28—H28B	109.5
C12—C11—C9	112.3 (2)	C4—C28—H28C	109.5
C12—C11—H11A	109.2	H28A—C28—H28C	109.5
C9—C11—H11A	109.2	H28B—C28—H28C	109.5
C12—C11—H11B	109.2	C4—C29—H29A	109.5
C9—C11—H11B	109.2	C4—C29—H29B	109.5
H11A—C11—H11B	107.9	H29A—C29—H29B	109.5
C11—C12—C13	113.5 (2)	C4—C29—H29C	109.5
C11—C12—H12A	108.9	H29A—C29—H29C	109.5
C13—C12—H12A	108.9	H29B—C29—H29C	109.5
C11—C12—H12B	108.9	C8—C30—C2	124.3 (3)
C13—C12—H12B	108.9	C8—C30—H30	117.9
H12A—C12—H12B	107.7	C2—C30—H30	117.9
C12—C13—C18	108.1 (2)	O3—C31—H31A	109.5
C12—C13—C17	110.4 (2)	O3—C31—H31B	109.5
C18—C13—C17	110.6 (2)	H31A—C31—H31B	109.5
C12—C13—C14	108.9 (2)	O3—C31—H31C	109.5
C18—C13—C14	111.1 (2)	H31A—C31—H31C	109.5
C17—C13—C14	107.7 (2)	H31B—C31—H31C	109.5
C15—C14—C8	114.7 (3)	C25—C32—H32A	109.5
C15—C14—C13	108.5 (2)	C25—C32—H32B	109.5
C8—C14—C13	113.5 (2)	H32A—C32—H32B	109.5
C15—C14—H14	106.5	C25—C32—H32C	109.5
C8—C14—H14	106.5	H32A—C32—H32C	109.5
C13—C14—H14	106.5	H32B—C32—H32C	109.5
C16—C15—C14	115.6 (3)	C16—O1—C17	122.7 (2)
C16—C15—H15A	108.4	C24—O2—C3	118.9 (2)
C14—C15—H15A	108.4	C7—O3—C31	116.1 (3)
C16—C15—H15B	108.4	C23—O6—C21	105.9 (2)
C14—C15—H15B	108.4	C6—O7—H7	109.5
H15A—C15—H15B	107.4

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7···O5	0.82	2.15	2.640 (3)	119
C18—H18B···O9^i	0.96	2.59	3.435 (4)	147
C21—H21···O7^ii	0.93	2.58	3.510 (4)	174
C22—H22···O8^iii	0.93	2.38	3.276 (4)	162

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