(4-Meth-oxy-phen-yl)(4-propyl-cyclo-hex-yl)methanone.

The asymmetric unit of the title compound, C17H24O2, contains two independent mol-ecules with different conformations. The least-squares plane through the cyclohexane ring makes dihedral angles of 52.9 (5) and 81.4 (4)° with the benzene ring in the two molecules. The cyclo-hexane ring adopts a chair conformation in both mol-ecules. In the crystal, weak C-H⋯O hydrogen bonds link mol-ecules related by translation in [100] into two crystallographically independent chains.

Related literature

For the anti­hyperglycemic activity of SGLT2 inhibitors, see: Washburn (2009 ▶); Zhao et al. (2011 ▶); Shao et al. (2011 ▶). For the structure of (5-bromo-2-meth­oxy­phen­yl)(4-ethyl­cyclo­hex­yl)methanone, see: Wang et al. (2011 ▶).

Experimental

Crystal data

C17H24O2

M = 260.36

Triclinic,

a = 5.679 (1) Å

b = 7.3260 (12) Å

c = 35.020 (4) Å

α = 93.74 (1)°

β = 91.877 (6)°

γ = 94.436 (1)°

V = 1448.5 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 113 K

0.18 × 0.16 × 0.14 mm

Data collection

Rigaku Saturn724 CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2009 ▶) T min = 0.986, T max = 0.989

14496 measured reflections

6762 independent reflections

5234 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.129

S = 1.03

6762 reflections

347 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2009 ▶); 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813003644/cv5385sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813003644/cv5385Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813003644/cv5385Isup3.cml

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

C17H24O2	Z = 4
Mr = 260.36	F(000) = 568
Triclinic, P1	Dx = 1.194 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71075 Å
a = 5.679 (1) Å	Cell parameters from 3880 reflections
b = 7.3260 (12) Å	θ = 1.7–27.9°
c = 35.020 (4) Å	µ = 0.08 mm−1
α = 93.74 (1)°	T = 113 K
β = 91.877 (6)°	Prism, colorless
γ = 94.436 (1)°	0.18 × 0.16 × 0.14 mm
V = 1448.5 (4) Å3

Rigaku Saturn724 CCD diffractometer	6762 independent reflections
Radiation source: rotating anode	5234 reflections with I > 2σ(I)
Multilayer monochromator	Rint = 0.027
Detector resolution: 14.222 pixels mm-1	θmax = 27.9°, θmin = 1.8°
ω scans	h = −7→7
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2009)	k = −9→9
Tmin = 0.986, Tmax = 0.989	l = −45→45
14496 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0748P)2] where P = (Fo2 + 2Fc2)/3
6762 reflections	(Δ/σ)max = 0.001
347 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.21 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	0.99880 (12)	0.35024 (11)	0.15912 (2)	0.0289 (2)
O2	0.66126 (13)	0.59253 (10)	0.32334 (2)	0.02519 (18)
O3	−0.01039 (13)	1.20793 (12)	0.33989 (2)	0.0331 (2)
O4	0.30237 (13)	0.86232 (11)	0.18076 (2)	0.02688 (19)
C1	0.79648 (17)	0.37013 (14)	0.16884 (3)	0.0199 (2)
C2	0.75366 (17)	0.43668 (13)	0.20893 (3)	0.0182 (2)
C3	0.94045 (17)	0.53011 (13)	0.23066 (3)	0.0200 (2)
H3	1.0873	0.5551	0.2190	0.024*
C4	0.91789 (17)	0.58768 (14)	0.26880 (3)	0.0210 (2)
H4	1.0461	0.6539	0.2830	0.025*
C5	0.70437 (18)	0.54689 (13)	0.28593 (3)	0.0197 (2)
C6	0.51423 (17)	0.45635 (13)	0.26461 (3)	0.0207 (2)
H6	0.3679	0.4310	0.2763	0.025*
C7	0.53761 (17)	0.40306 (13)	0.22639 (3)	0.0200 (2)
H7	0.4062	0.3432	0.2119	0.024*
C8	0.8581 (2)	0.66708 (16)	0.34736 (3)	0.0295 (3)
H8A	0.9838	0.5827	0.3462	0.035*
H8B	0.8084	0.6839	0.3738	0.035*
H8C	0.9171	0.7858	0.3386	0.035*
C9	0.59203 (17)	0.33767 (14)	0.13965 (3)	0.0208 (2)
H9	0.4431	0.3066	0.1531	0.025*
C10	0.63021 (19)	0.18261 (14)	0.10969 (3)	0.0246 (2)
H10A	0.7868	0.2058	0.0986	0.030*
H10B	0.6292	0.0652	0.1222	0.030*
C11	0.43893 (19)	0.16664 (14)	0.07775 (3)	0.0248 (2)
H11A	0.2841	0.1324	0.0886	0.030*
H11B	0.4724	0.0677	0.0585	0.030*
C12	0.42516 (18)	0.34571 (14)	0.05803 (3)	0.0216 (2)
H12	0.5817	0.3762	0.0468	0.026*
C13	0.38275 (19)	0.49986 (15)	0.08810 (3)	0.0240 (2)
H13A	0.3811	0.6171	0.0756	0.029*
H13B	0.2260	0.4743	0.0990	0.029*
C14	0.57195 (19)	0.51957 (14)	0.12039 (3)	0.0241 (2)
H14A	0.5325	0.6157	0.1398	0.029*
H14B	0.7263	0.5589	0.1100	0.029*
C15	0.23631 (18)	0.33204 (15)	0.02564 (3)	0.0242 (2)
H15A	0.0826	0.2907	0.0360	0.029*
H15B	0.2219	0.4561	0.0166	0.029*
C16	0.2837 (2)	0.20226 (16)	−0.00861 (3)	0.0273 (2)
H16A	0.4423	0.2373	−0.0180	0.033*
H16B	0.2845	0.0758	−0.0002	0.033*
C17	0.1010 (2)	0.20485 (17)	−0.04126 (3)	0.0315 (3)
H17A	−0.0554	0.1643	−0.0325	0.038*
H17B	0.1419	0.1221	−0.0627	0.038*
H17C	0.0987	0.3298	−0.0496	0.038*
C18	0.18165 (18)	1.15443 (14)	0.33140 (3)	0.0213 (2)
C19	0.21375 (17)	1.07129 (13)	0.29201 (3)	0.0192 (2)
C20	0.03936 (17)	1.08960 (13)	0.26396 (3)	0.0200 (2)
H20	−0.0977	1.1492	0.2707	0.024*
C21	0.06192 (17)	1.02246 (14)	0.22640 (3)	0.0210 (2)
H21	−0.0576	1.0371	0.2075	0.025*
C22	0.26183 (18)	0.93344 (13)	0.21679 (3)	0.0209 (2)
C23	0.43692 (17)	0.91194 (14)	0.24449 (3)	0.0212 (2)
H23	0.5717	0.8492	0.2379	0.025*
C24	0.41410 (17)	0.98210 (14)	0.28166 (3)	0.0207 (2)
H24	0.5356	0.9698	0.3004	0.025*
C25	0.1211 (2)	0.87346 (16)	0.15194 (3)	0.0308 (3)
H25A	−0.0256	0.8085	0.1595	0.037*
H25B	0.1695	0.8170	0.1276	0.037*
H25C	0.0951	1.0025	0.1489	0.037*
C26	0.38631 (17)	1.17056 (14)	0.36072 (3)	0.0203 (2)
H26	0.5374	1.1922	0.3472	0.024*
C27	0.36464 (18)	1.33026 (14)	0.39046 (3)	0.0230 (2)
H27A	0.3720	1.4468	0.3776	0.028*
H27B	0.2095	1.3151	0.4025	0.028*
C28	0.56124 (18)	1.33969 (14)	0.42140 (3)	0.0240 (2)
H28A	0.5397	1.4424	0.4404	0.029*
H28B	0.7156	1.3647	0.4096	0.029*
C29	0.56315 (18)	1.16106 (14)	0.44176 (3)	0.0220 (2)
H29	0.4071	1.1399	0.4538	0.026*
C30	0.58677 (19)	1.00186 (14)	0.41190 (3)	0.0235 (2)
H30A	0.7421	1.0185	0.4000	0.028*
H30B	0.5812	0.8853	0.4248	0.028*
C31	0.39091 (18)	0.98958 (14)	0.38069 (3)	0.0231 (2)
H31A	0.2364	0.9614	0.3922	0.028*
H31B	0.4163	0.8884	0.3615	0.028*
C32	0.75613 (19)	1.16748 (15)	0.47336 (3)	0.0242 (2)
H32A	0.7643	1.0425	0.4823	0.029*
H32B	0.9100	1.2033	0.4624	0.029*
C33	0.7207 (2)	1.29943 (15)	0.50788 (3)	0.0268 (2)
H33A	0.7267	1.4263	0.4996	0.032*
H33B	0.5621	1.2702	0.5179	0.032*
C34	0.9062 (2)	1.28984 (16)	0.53987 (3)	0.0307 (3)
H34A	0.9018	1.1644	0.5481	0.037*
H34B	0.8731	1.3743	0.5615	0.037*
H34C	1.0631	1.3246	0.5305	0.037*

	U11	U22	U33	U12	U13	U23
O1	0.0202 (4)	0.0423 (5)	0.0243 (4)	0.0054 (3)	0.0018 (3)	−0.0008 (3)
O2	0.0282 (4)	0.0283 (4)	0.0184 (4)	0.0021 (3)	0.0006 (3)	−0.0026 (3)
O3	0.0219 (4)	0.0504 (5)	0.0271 (4)	0.0089 (4)	0.0020 (3)	−0.0033 (4)
O4	0.0308 (4)	0.0312 (4)	0.0187 (4)	0.0075 (3)	−0.0016 (3)	−0.0025 (3)
C1	0.0203 (5)	0.0204 (5)	0.0191 (5)	0.0023 (4)	0.0004 (4)	0.0026 (4)
C2	0.0188 (5)	0.0171 (5)	0.0190 (5)	0.0026 (4)	−0.0008 (4)	0.0035 (4)
C3	0.0182 (5)	0.0200 (5)	0.0221 (5)	0.0015 (4)	0.0001 (4)	0.0041 (4)
C4	0.0192 (5)	0.0196 (5)	0.0239 (5)	0.0007 (4)	−0.0028 (4)	0.0016 (4)
C5	0.0250 (5)	0.0171 (5)	0.0175 (5)	0.0047 (4)	0.0008 (4)	0.0024 (4)
C6	0.0195 (5)	0.0187 (5)	0.0243 (5)	0.0008 (4)	0.0037 (4)	0.0035 (4)
C7	0.0180 (5)	0.0176 (5)	0.0240 (5)	0.0000 (4)	−0.0010 (4)	0.0012 (4)
C8	0.0341 (6)	0.0328 (6)	0.0206 (5)	0.0039 (5)	−0.0051 (4)	−0.0045 (4)
C9	0.0184 (5)	0.0265 (5)	0.0174 (5)	0.0024 (4)	−0.0004 (4)	0.0007 (4)
C10	0.0285 (6)	0.0226 (5)	0.0226 (5)	0.0060 (4)	−0.0039 (4)	−0.0010 (4)
C11	0.0290 (6)	0.0229 (5)	0.0217 (5)	0.0019 (4)	−0.0047 (4)	−0.0021 (4)
C12	0.0217 (5)	0.0264 (5)	0.0166 (5)	0.0032 (4)	−0.0003 (4)	−0.0006 (4)
C13	0.0291 (6)	0.0250 (5)	0.0185 (5)	0.0082 (4)	−0.0028 (4)	−0.0001 (4)
C14	0.0282 (6)	0.0242 (5)	0.0198 (5)	0.0057 (4)	−0.0026 (4)	−0.0021 (4)
C15	0.0261 (6)	0.0284 (6)	0.0182 (5)	0.0055 (4)	−0.0022 (4)	−0.0005 (4)
C16	0.0319 (6)	0.0291 (6)	0.0207 (5)	0.0056 (5)	−0.0028 (4)	−0.0022 (4)
C17	0.0382 (7)	0.0336 (6)	0.0215 (5)	0.0033 (5)	−0.0072 (5)	−0.0029 (5)
C18	0.0203 (5)	0.0230 (5)	0.0208 (5)	0.0008 (4)	0.0020 (4)	0.0038 (4)
C19	0.0188 (5)	0.0179 (5)	0.0207 (5)	−0.0016 (4)	0.0005 (4)	0.0028 (4)
C20	0.0173 (5)	0.0191 (5)	0.0237 (5)	0.0001 (4)	0.0007 (4)	0.0034 (4)
C21	0.0205 (5)	0.0204 (5)	0.0221 (5)	0.0002 (4)	−0.0031 (4)	0.0037 (4)
C22	0.0252 (5)	0.0178 (5)	0.0196 (5)	−0.0002 (4)	0.0024 (4)	0.0019 (4)
C23	0.0204 (5)	0.0200 (5)	0.0238 (5)	0.0028 (4)	0.0020 (4)	0.0034 (4)
C24	0.0193 (5)	0.0216 (5)	0.0215 (5)	0.0008 (4)	−0.0009 (4)	0.0046 (4)
C25	0.0371 (7)	0.0338 (6)	0.0211 (5)	0.0078 (5)	−0.0053 (4)	−0.0025 (4)
C26	0.0197 (5)	0.0229 (5)	0.0181 (5)	0.0016 (4)	0.0009 (4)	0.0010 (4)
C27	0.0250 (5)	0.0231 (5)	0.0209 (5)	0.0045 (4)	−0.0003 (4)	0.0003 (4)
C28	0.0267 (6)	0.0231 (5)	0.0218 (5)	0.0023 (4)	−0.0017 (4)	−0.0018 (4)
C29	0.0229 (5)	0.0251 (5)	0.0181 (5)	0.0030 (4)	0.0003 (4)	−0.0001 (4)
C30	0.0288 (6)	0.0226 (5)	0.0192 (5)	0.0049 (4)	−0.0012 (4)	0.0001 (4)
C31	0.0260 (5)	0.0228 (5)	0.0202 (5)	0.0010 (4)	−0.0001 (4)	0.0001 (4)
C32	0.0259 (6)	0.0274 (6)	0.0196 (5)	0.0057 (4)	−0.0017 (4)	−0.0002 (4)
C33	0.0319 (6)	0.0275 (6)	0.0207 (5)	0.0051 (4)	−0.0020 (4)	−0.0017 (4)
C34	0.0361 (7)	0.0326 (6)	0.0226 (5)	0.0027 (5)	−0.0063 (5)	−0.0010 (4)

O1—C1	1.2256 (12)	C17—H17A	0.9800
O2—C5	1.3657 (11)	C17—H17B	0.9800
O2—C8	1.4280 (12)	C17—H17C	0.9800
O3—C18	1.2261 (12)	C18—C19	1.4937 (13)
O4—C22	1.3669 (11)	C18—C26	1.5178 (14)
O4—C25	1.4284 (12)	C19—C20	1.3921 (13)
C1—C2	1.4897 (13)	C19—C24	1.4014 (14)
C1—C9	1.5157 (13)	C20—C21	1.3874 (13)
C2—C3	1.3927 (13)	C20—H20	0.9500
C2—C7	1.4007 (13)	C21—C22	1.3922 (14)
C3—C4	1.3872 (13)	C21—H21	0.9500
C3—H3	0.9500	C22—C23	1.3913 (14)
C4—C5	1.3909 (14)	C23—C24	1.3816 (13)
C4—H4	0.9500	C23—H23	0.9500
C5—C6	1.3910 (14)	C24—H24	0.9500
C6—C7	1.3834 (13)	C25—H25A	0.9800
C6—H6	0.9500	C25—H25B	0.9800
C7—H7	0.9500	C25—H25C	0.9800
C8—H8A	0.9800	C26—C27	1.5298 (13)
C8—H8B	0.9800	C26—C31	1.5404 (14)
C8—H8C	0.9800	C26—H26	1.0000
C9—C10	1.5285 (13)	C27—C28	1.5246 (14)
C9—C14	1.5426 (15)	C27—H27A	0.9900
C9—H9	1.0000	C27—H27B	0.9900
C10—C11	1.5259 (14)	C28—C29	1.5311 (15)
C10—H10A	0.9900	C28—H28A	0.9900
C10—H10B	0.9900	C28—H28B	0.9900
C11—C12	1.5278 (15)	C29—C32	1.5277 (14)
C11—H11A	0.9900	C29—C30	1.5316 (13)
C11—H11B	0.9900	C29—H29	1.0000
C12—C15	1.5284 (14)	C30—C31	1.5270 (14)
C12—C13	1.5314 (13)	C30—H30A	0.9900
C12—H12	1.0000	C30—H30B	0.9900
C13—C14	1.5262 (14)	C31—H31A	0.9900
C13—H13A	0.9900	C31—H31B	0.9900
C13—H13B	0.9900	C32—C33	1.5263 (13)
C14—H14A	0.9900	C32—H32A	0.9900
C14—H14B	0.9900	C32—H32B	0.9900
C15—C16	1.5253 (13)	C33—C34	1.5210 (15)
C15—H15A	0.9900	C33—H33A	0.9900
C15—H15B	0.9900	C33—H33B	0.9900
C16—C17	1.5207 (15)	C34—H34A	0.9800
C16—H16A	0.9900	C34—H34B	0.9800
C16—H16B	0.9900	C34—H34C	0.9800
C5—O2—C8	117.03 (8)	H17B—C17—H17C	109.5
C22—O4—C25	117.07 (8)	O3—C18—C19	119.74 (9)
O1—C1—C2	119.73 (9)	O3—C18—C26	120.49 (9)
O1—C1—C9	120.15 (8)	C19—C18—C26	119.77 (8)
C2—C1—C9	120.03 (8)	C20—C19—C24	118.60 (9)
C3—C2—C7	118.32 (9)	C20—C19—C18	118.07 (9)
C3—C2—C1	118.42 (9)	C24—C19—C18	123.28 (9)
C7—C2—C1	123.20 (8)	C21—C20—C19	121.24 (9)
C4—C3—C2	121.78 (9)	C21—C20—H20	119.4
C4—C3—H3	119.1	C19—C20—H20	119.4
C2—C3—H3	119.1	C20—C21—C22	119.19 (9)
C3—C4—C5	118.89 (9)	C20—C21—H21	120.4
C3—C4—H4	120.6	C22—C21—H21	120.4
C5—C4—H4	120.6	O4—C22—C23	115.43 (9)
O2—C5—C4	124.58 (9)	O4—C22—C21	124.12 (9)
O2—C5—C6	115.13 (9)	C23—C22—C21	120.46 (9)
C4—C5—C6	120.28 (9)	C24—C23—C22	119.76 (9)
C7—C6—C5	120.20 (9)	C24—C23—H23	120.1
C7—C6—H6	119.9	C22—C23—H23	120.1
C5—C6—H6	119.9	C23—C24—C19	120.73 (9)
C6—C7—C2	120.46 (9)	C23—C24—H24	119.6
C6—C7—H7	119.8	C19—C24—H24	119.6
C2—C7—H7	119.8	O4—C25—H25A	109.5
O2—C8—H8A	109.5	O4—C25—H25B	109.5
O2—C8—H8B	109.5	H25A—C25—H25B	109.5
H8A—C8—H8B	109.5	O4—C25—H25C	109.5
O2—C8—H8C	109.5	H25A—C25—H25C	109.5
H8A—C8—H8C	109.5	H25B—C25—H25C	109.5
H8B—C8—H8C	109.5	C18—C26—C27	111.17 (8)
C1—C9—C10	112.01 (8)	C18—C26—C31	109.14 (8)
C1—C9—C14	106.69 (8)	C27—C26—C31	109.91 (8)
C10—C9—C14	110.37 (8)	C18—C26—H26	108.9
C1—C9—H9	109.2	C27—C26—H26	108.9
C10—C9—H9	109.2	C31—C26—H26	108.9
C14—C9—H9	109.2	C28—C27—C26	111.38 (8)
C11—C10—C9	111.57 (8)	C28—C27—H27A	109.4
C11—C10—H10A	109.3	C26—C27—H27A	109.4
C9—C10—H10A	109.3	C28—C27—H27B	109.4
C11—C10—H10B	109.3	C26—C27—H27B	109.4
C9—C10—H10B	109.3	H27A—C27—H27B	108.0
H10A—C10—H10B	108.0	C27—C28—C29	111.88 (9)
C10—C11—C12	112.08 (9)	C27—C28—H28A	109.2
C10—C11—H11A	109.2	C29—C28—H28A	109.2
C12—C11—H11A	109.2	C27—C28—H28B	109.2
C10—C11—H11B	109.2	C29—C28—H28B	109.2
C12—C11—H11B	109.2	H28A—C28—H28B	107.9
H11A—C11—H11B	107.9	C32—C29—C28	113.07 (9)
C11—C12—C15	112.92 (9)	C32—C29—C30	111.21 (8)
C11—C12—C13	109.03 (8)	C28—C29—C30	108.89 (8)
C15—C12—C13	111.00 (8)	C32—C29—H29	107.8
C11—C12—H12	107.9	C28—C29—H29	107.8
C15—C12—H12	107.9	C30—C29—H29	107.8
C13—C12—H12	107.9	C31—C30—C29	112.01 (8)
C14—C13—C12	112.18 (8)	C31—C30—H30A	109.2
C14—C13—H13A	109.2	C29—C30—H30A	109.2
C12—C13—H13A	109.2	C31—C30—H30B	109.2
C14—C13—H13B	109.2	C29—C30—H30B	109.2
C12—C13—H13B	109.2	H30A—C30—H30B	107.9
H13A—C13—H13B	107.9	C30—C31—C26	111.24 (8)
C13—C14—C9	111.59 (9)	C30—C31—H31A	109.4
C13—C14—H14A	109.3	C26—C31—H31A	109.4
C9—C14—H14A	109.3	C30—C31—H31B	109.4
C13—C14—H14B	109.3	C26—C31—H31B	109.4
C9—C14—H14B	109.3	H31A—C31—H31B	108.0
H14A—C14—H14B	108.0	C33—C32—C29	114.64 (9)
C16—C15—C12	114.86 (9)	C33—C32—H32A	108.6
C16—C15—H15A	108.6	C29—C32—H32A	108.6
C12—C15—H15A	108.6	C33—C32—H32B	108.6
C16—C15—H15B	108.6	C29—C32—H32B	108.6
C12—C15—H15B	108.6	H32A—C32—H32B	107.6
H15A—C15—H15B	107.5	C34—C33—C32	112.69 (9)
C17—C16—C15	112.75 (9)	C34—C33—H33A	109.1
C17—C16—H16A	109.0	C32—C33—H33A	109.1
C15—C16—H16A	109.0	C34—C33—H33B	109.1
C17—C16—H16B	109.0	C32—C33—H33B	109.1
C15—C16—H16B	109.0	H33A—C33—H33B	107.8
H16A—C16—H16B	107.8	C33—C34—H34A	109.5
C16—C17—H17A	109.5	C33—C34—H34B	109.5
C16—C17—H17B	109.5	H34A—C34—H34B	109.5
H17A—C17—H17B	109.5	C33—C34—H34C	109.5
C16—C17—H17C	109.5	H34A—C34—H34C	109.5
H17A—C17—H17C	109.5	H34B—C34—H34C	109.5
O1—C1—C2—C3	20.66 (14)	O3—C18—C19—C20	12.36 (14)
C9—C1—C2—C3	−155.84 (9)	C26—C18—C19—C20	−168.16 (9)
O1—C1—C2—C7	−156.50 (10)	O3—C18—C19—C24	−170.06 (10)
C9—C1—C2—C7	26.99 (14)	C26—C18—C19—C24	9.42 (14)
C7—C2—C3—C4	0.78 (15)	C24—C19—C20—C21	−0.35 (14)
C1—C2—C3—C4	−176.52 (9)	C18—C19—C20—C21	177.34 (9)
C2—C3—C4—C5	1.54 (15)	C19—C20—C21—C22	0.70 (14)
C8—O2—C5—C4	−7.96 (14)	C25—O4—C22—C23	176.92 (9)
C8—O2—C5—C6	173.21 (9)	C25—O4—C22—C21	−3.15 (14)
C3—C4—C5—O2	178.66 (9)	C20—C21—C22—O4	−179.91 (9)
C3—C4—C5—C6	−2.56 (15)	C20—C21—C22—C23	0.02 (15)
O2—C5—C6—C7	−179.86 (9)	O4—C22—C23—C24	178.85 (9)
C4—C5—C6—C7	1.25 (15)	C21—C22—C23—C24	−1.08 (15)
C5—C6—C7—C2	1.13 (15)	C22—C23—C24—C19	1.44 (15)
C3—C2—C7—C6	−2.13 (15)	C20—C19—C24—C23	−0.73 (14)
C1—C2—C7—C6	175.04 (9)	C18—C19—C24—C23	−178.29 (9)
O1—C1—C9—C10	34.71 (13)	O3—C18—C26—C27	−27.44 (14)
C2—C1—C9—C10	−148.79 (9)	C19—C18—C26—C27	153.09 (9)
O1—C1—C9—C14	−86.17 (11)	O3—C18—C26—C31	93.96 (11)
C2—C1—C9—C14	90.32 (10)	C19—C18—C26—C31	−85.51 (11)
C1—C9—C10—C11	−172.99 (8)	C18—C26—C27—C28	176.42 (8)
C14—C9—C10—C11	−54.26 (11)	C31—C26—C27—C28	55.47 (11)
C9—C10—C11—C12	57.09 (12)	C26—C27—C28—C29	−57.59 (11)
C10—C11—C12—C15	179.38 (8)	C27—C28—C29—C32	−179.12 (8)
C10—C11—C12—C13	−56.75 (11)	C27—C28—C29—C30	56.73 (11)
C11—C12—C13—C14	56.27 (11)	C32—C29—C30—C31	178.27 (8)
C15—C12—C13—C14	−178.73 (8)	C28—C29—C30—C31	−56.49 (11)
C12—C13—C14—C9	−55.85 (12)	C29—C30—C31—C26	56.83 (11)
C1—C9—C14—C13	175.68 (8)	C18—C26—C31—C30	−177.24 (8)
C10—C9—C14—C13	53.76 (11)	C27—C26—C31—C30	−55.08 (11)
C11—C12—C15—C16	−66.01 (12)	C28—C29—C32—C33	67.56 (12)
C13—C12—C15—C16	171.21 (9)	C30—C29—C32—C33	−169.58 (9)
C12—C15—C16—C17	−175.54 (9)	C29—C32—C33—C34	175.41 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1i	1.00	2.58	3.4661 (14)	147
C26—H26···O3ii	1.00	2.58	3.5200 (14)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O1i	1.00	2.58	3.4661 (14)	147
C26—H26⋯O3ii	1.00	2.58	3.5200 (14)	156

Symmetry codes: (i) ; (ii) .