Methyl 3-[(chloro-meth-oxy)carbon-yloxy]-7-hy-droxy-cholan-24-oate.

The title compound, C27H43ClO6, is a derivative of urso-deoxy-cholic acid, in which the OH group at the 3-position is substituted by a chloro-meth-oxy-carbon-yloxy substituent and the carb-oxy-lic acid group at the 24-position is methyl-ated. The A and B rings are cis-fused, while all other rings are trans-fused. In the crystal, two adjacent mol-ecules located along the b-axis direction are inter-locked head-to-tail due to weak C-H⋯O hydrogen bonds. Therefore each mol-ecule is linked to four neighbouring mol-ecules by four C-H⋯O hydrogen bonds, with the OH group at the 7-position and the carbonyl O atom of the ester group acting as the acceptor sites.

Related literature

For the synthesis of the title compound, see: von Geldern et al. (2004 ▶); For similar structures, see: Kannan et al. (2001 ▶); Lindley & Carey et al. (1987 ▶).

Experimental

Crystal data

C27H43ClO6

M = 499.06

Orthorhombic,

a = 7.8896 (13) Å

b = 10.9493 (17) Å

c = 30.683 (5) Å

V = 2650.6 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 294 K

0.24 × 0.20 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer

15292 measured reflections

5411 independent reflections

3191 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.118

S = 0.94

5411 reflections

311 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 2309 Friedel pairs

Flack parameter: −0.10 (9)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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: publCIF (Westrip, 2010) ▶.

Crystal structure: contains datablock(s) . DOI: 10.1107/S160053681301725X/im2434sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681301725X/im2434Isup2.hkl

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

C27H43ClO6	F(000) = 1080
Mr = 499.06	Dx = 1.251 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2869 reflections
a = 7.8896 (13) Å	θ = 2.3–20.2°
b = 10.9493 (17) Å	µ = 0.18 mm−1
c = 30.683 (5) Å	T = 294 K
V = 2650.6 (7) Å3	Block, colorless
Z = 4	0.24 × 0.20 × 0.12 mm

Bruker APEXII CCD diffractometer	3191 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.054
Graphite monochromator	θmax = 26.4°, θmin = 2.0°
φ and ω scans	h = −9→9
15292 measured reflections	k = −13→13
5411 independent reflections	l = −38→24

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050	H-atom parameters constrained
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.0543P)2 + 0.1843P] where P = (Fo2 + 2Fc2)/3
S = 0.94	(Δ/σ)max = 0.006
5411 reflections	Δρmax = 0.15 e Å−3
311 parameters	Δρmin = −0.19 e Å−3
0 restraints	Absolute structure: Flack (1983), 2309 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.10 (9)

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
Cl1	0.32107 (15)	0.26524 (10)	0.18096 (3)	0.0899 (4)
O1	0.2665 (3)	0.37444 (17)	0.31505 (6)	0.0499 (5)
O2	−0.3225 (2)	0.4663 (2)	0.46546 (7)	0.0736 (7)
H2	−0.3270	0.4100	0.4831	0.110*
O3	0.1100 (3)	0.4228 (2)	0.25576 (7)	0.0717 (7)
O4	0.2450 (3)	0.24219 (18)	0.26367 (6)	0.0657 (7)
O5	0.1643 (4)	0.0724 (2)	0.72053 (8)	0.0823 (8)
O6	0.2415 (3)	0.18771 (19)	0.77669 (7)	0.0623 (6)
C1	0.3092 (4)	0.6337 (2)	0.39347 (9)	0.0435 (7)
H1A	0.3016	0.7011	0.3730	0.052*
H1B	0.3992	0.6527	0.4139	0.052*
C2	0.3587 (3)	0.5194 (2)	0.36840 (9)	0.0408 (7)
H2A	0.4639	0.5334	0.3528	0.049*
H2B	0.3758	0.4521	0.3885	0.049*
C3	0.2202 (3)	0.4882 (3)	0.33670 (9)	0.0416 (7)
H3	0.2097	0.5535	0.3150	0.050*
C4	0.0533 (3)	0.4714 (3)	0.35987 (9)	0.0439 (7)
H4A	0.0613	0.4012	0.3791	0.053*
H4B	−0.0342	0.4545	0.3385	0.053*
C5	0.0019 (3)	0.5833 (3)	0.38662 (10)	0.0415 (7)
H5	−0.0158	0.6502	0.3659	0.050*
C6	−0.1667 (4)	0.5618 (3)	0.40940 (9)	0.0508 (8)
H6A	−0.2474	0.5302	0.3884	0.061*
H6B	−0.2097	0.6394	0.4199	0.061*
C7	−0.1550 (3)	0.4733 (3)	0.44751 (9)	0.0462 (7)
H7	−0.1227	0.3926	0.4365	0.055*
C8	−0.0229 (3)	0.5153 (3)	0.48090 (9)	0.0351 (6)
H8	−0.0600	0.5940	0.4927	0.042*
C9	0.1503 (3)	0.5350 (2)	0.45808 (8)	0.0342 (6)
H9	0.1819	0.4558	0.4457	0.041*
C10	0.1415 (3)	0.6260 (2)	0.41883 (9)	0.0361 (6)
C11	0.2904 (4)	0.5677 (3)	0.49034 (9)	0.0459 (8)
H11A	0.2699	0.6494	0.5014	0.055*
H11B	0.3979	0.5688	0.4750	0.055*
C12	0.3042 (3)	0.4796 (3)	0.52914 (9)	0.0442 (7)
H12A	0.3393	0.3998	0.5188	0.053*
H12B	0.3897	0.5091	0.5492	0.053*
C13	0.1340 (3)	0.4681 (2)	0.55303 (9)	0.0359 (7)
C14	−0.0003 (3)	0.4264 (3)	0.51936 (9)	0.0380 (7)
H14	0.0433	0.3504	0.5067	0.046*
C15	−0.1512 (4)	0.3896 (3)	0.54761 (10)	0.0517 (8)
H15A	−0.2190	0.3277	0.5332	0.062*
H15B	−0.2223	0.4597	0.5539	0.062*
C16	−0.0713 (4)	0.3389 (3)	0.58960 (10)	0.0576 (9)
H16A	−0.0917	0.2517	0.5918	0.069*
H16B	−0.1206	0.3784	0.6149	0.069*
C17	0.1219 (4)	0.3648 (3)	0.58750 (9)	0.0426 (7)
H17	0.1754	0.2924	0.5748	0.051*
C18	0.1007 (4)	0.7560 (3)	0.43452 (10)	0.0541 (8)
H18A	0.1943	0.7871	0.4511	0.081*
H18B	0.0010	0.7543	0.4525	0.081*
H18C	0.0812	0.8078	0.4098	0.081*
C19	0.0859 (4)	0.5906 (2)	0.57389 (9)	0.0462 (8)
H19A	0.0679	0.6503	0.5515	0.069*
H19B	0.1758	0.6172	0.5927	0.069*
H19C	−0.0162	0.5809	0.5906	0.069*
C20	0.2012 (4)	0.3833 (3)	0.63295 (9)	0.0481 (8)
H20	0.1423	0.4517	0.6469	0.058*
C21	0.1710 (4)	0.2695 (3)	0.66091 (9)	0.0549 (8)
H21A	0.0532	0.2455	0.6580	0.066*
H21B	0.2399	0.2034	0.6495	0.066*
C22	0.2112 (5)	0.2856 (3)	0.70923 (10)	0.0659 (10)
H22A	0.3244	0.3192	0.7121	0.079*
H22B	0.1325	0.3441	0.7216	0.079*
C23	0.2014 (4)	0.1701 (3)	0.73474 (10)	0.0535 (8)
C24	0.2399 (5)	0.0802 (3)	0.80385 (11)	0.0825 (12)
H24A	0.1299	0.0429	0.8027	0.124*
H24B	0.2653	0.1028	0.8334	0.124*
H24C	0.3236	0.0234	0.7936	0.124*
C25	0.3888 (4)	0.4142 (4)	0.63165 (12)	0.0798 (12)
H25A	0.4474	0.3547	0.6143	0.120*
H25B	0.4336	0.4135	0.6607	0.120*
H25C	0.4038	0.4938	0.6191	0.120*
C26	0.1968 (4)	0.3558 (3)	0.27627 (10)	0.0494 (8)
C27	0.1876 (5)	0.2065 (3)	0.22191 (9)	0.0642 (10)
H27A	0.0731	0.2362	0.2174	0.077*
H27B	0.1854	0.1181	0.2201	0.077*

	U11	U22	U33	U12	U13	U23
Cl1	0.1037 (8)	0.1095 (8)	0.0566 (5)	−0.0270 (6)	0.0159 (6)	−0.0190 (5)
O1	0.0637 (13)	0.0502 (12)	0.0358 (11)	0.0123 (10)	−0.0067 (11)	−0.0087 (10)
O2	0.0304 (11)	0.126 (2)	0.0641 (15)	−0.0057 (12)	0.0029 (12)	0.0148 (14)
O3	0.0891 (18)	0.0694 (15)	0.0566 (14)	0.0211 (14)	−0.0233 (15)	−0.0142 (12)
O4	0.1050 (19)	0.0487 (12)	0.0433 (12)	0.0106 (13)	−0.0066 (13)	−0.0096 (10)
O5	0.124 (2)	0.0533 (14)	0.0699 (16)	−0.0114 (15)	−0.0356 (17)	0.0132 (13)
O6	0.0814 (17)	0.0611 (13)	0.0445 (12)	0.0078 (12)	0.0031 (13)	0.0078 (11)
C1	0.0495 (19)	0.0389 (16)	0.0421 (16)	−0.0033 (14)	−0.0036 (15)	−0.0019 (14)
C2	0.0362 (15)	0.0453 (16)	0.0410 (16)	−0.0001 (14)	0.0027 (14)	−0.0016 (14)
C3	0.0423 (16)	0.0417 (16)	0.0407 (16)	0.0044 (14)	−0.0009 (15)	−0.0064 (13)
C4	0.0414 (17)	0.0485 (17)	0.0417 (18)	−0.0028 (14)	−0.0091 (15)	−0.0070 (15)
C5	0.0396 (17)	0.0435 (17)	0.0414 (17)	0.0053 (14)	−0.0066 (15)	0.0038 (15)
C6	0.0355 (16)	0.066 (2)	0.0505 (18)	0.0099 (15)	−0.0055 (16)	−0.0017 (16)
C7	0.0289 (15)	0.063 (2)	0.0468 (18)	0.0007 (15)	−0.0016 (15)	−0.0029 (16)
C8	0.0299 (14)	0.0360 (15)	0.0395 (16)	0.0043 (12)	−0.0013 (13)	−0.0072 (13)
C9	0.0304 (14)	0.0336 (15)	0.0387 (15)	0.0060 (12)	−0.0013 (13)	−0.0043 (12)
C10	0.0365 (15)	0.0327 (15)	0.0392 (15)	0.0028 (13)	0.0012 (14)	−0.0045 (13)
C11	0.0340 (16)	0.0604 (19)	0.0434 (17)	−0.0018 (15)	−0.0007 (15)	−0.0012 (15)
C12	0.0372 (16)	0.0516 (17)	0.0438 (17)	0.0012 (14)	−0.0047 (15)	−0.0025 (14)
C13	0.0360 (15)	0.0339 (15)	0.0379 (16)	0.0008 (13)	−0.0009 (14)	−0.0016 (13)
C14	0.0327 (16)	0.0367 (15)	0.0444 (17)	0.0038 (13)	−0.0021 (15)	−0.0075 (14)
C15	0.0417 (17)	0.058 (2)	0.0554 (19)	−0.0081 (15)	−0.0026 (17)	0.0066 (16)
C16	0.0531 (19)	0.063 (2)	0.057 (2)	−0.0165 (16)	−0.0101 (18)	0.0185 (18)
C17	0.0471 (17)	0.0352 (16)	0.0455 (17)	0.0026 (13)	−0.0017 (16)	−0.0015 (14)
C18	0.065 (2)	0.0400 (17)	0.0569 (19)	0.0126 (16)	−0.0005 (18)	−0.0009 (15)
C19	0.0553 (19)	0.0382 (17)	0.0452 (18)	0.0000 (15)	0.0015 (16)	−0.0002 (14)
C20	0.0547 (19)	0.0418 (16)	0.0478 (18)	−0.0083 (15)	−0.0081 (17)	0.0067 (14)
C21	0.059 (2)	0.0509 (19)	0.0547 (19)	−0.0017 (16)	−0.0068 (18)	0.0086 (15)
C22	0.096 (3)	0.050 (2)	0.0516 (19)	−0.0089 (19)	−0.014 (2)	0.0100 (16)
C23	0.055 (2)	0.051 (2)	0.054 (2)	0.0046 (17)	−0.0109 (18)	0.0041 (17)
C24	0.121 (3)	0.072 (2)	0.054 (2)	0.017 (2)	0.002 (2)	0.0246 (19)
C25	0.069 (2)	0.105 (3)	0.065 (2)	−0.031 (2)	−0.023 (2)	0.026 (2)
C26	0.058 (2)	0.049 (2)	0.0415 (18)	0.0017 (17)	0.0030 (18)	−0.0060 (16)
C27	0.091 (3)	0.060 (2)	0.0418 (18)	−0.0061 (19)	0.000 (2)	−0.0203 (16)

Cl1—C27	1.761 (3)	C11—H11B	0.9700
O1—C26	1.327 (3)	C12—C13	1.535 (4)
O1—C3	1.458 (3)	C12—H12A	0.9700
O2—C7	1.433 (3)	C12—H12B	0.9700
O2—H2	0.8200	C13—C19	1.534 (4)
O3—C26	1.185 (4)	C13—C14	1.549 (4)
O4—C26	1.357 (3)	C13—C17	1.551 (4)
O4—C27	1.414 (3)	C14—C15	1.526 (4)
O5—C23	1.191 (4)	C14—H14	0.9800
O6—C23	1.340 (4)	C15—C16	1.538 (4)
O6—C24	1.442 (3)	C15—H15A	0.9700
C1—C2	1.520 (4)	C15—H15B	0.9700
C1—C10	1.537 (4)	C16—C17	1.552 (4)
C1—H1A	0.9700	C16—H16A	0.9700
C1—H1B	0.9700	C16—H16B	0.9700
C2—C3	1.502 (3)	C17—C20	1.542 (4)
C2—H2A	0.9700	C17—H17	0.9800
C2—H2B	0.9700	C18—H18A	0.9600
C3—C4	1.508 (4)	C18—H18B	0.9600
C3—H3	0.9800	C18—H18C	0.9600
C4—C5	1.530 (4)	C19—H19A	0.9600
C4—H4A	0.9700	C19—H19B	0.9600
C4—H4B	0.9700	C19—H19C	0.9600
C5—C6	1.521 (4)	C20—C25	1.519 (4)
C5—C10	1.552 (4)	C20—C21	1.531 (4)
C5—H5	0.9800	C20—H20	0.9800
C6—C7	1.522 (4)	C21—C22	1.526 (4)
C6—H6A	0.9700	C21—H21A	0.9700
C6—H6B	0.9700	C21—H21B	0.9700
C7—C8	1.533 (4)	C22—C23	1.489 (4)
C7—H7	0.9800	C22—H22A	0.9700
C8—C14	1.540 (4)	C22—H22B	0.9700
C8—C9	1.550 (4)	C24—H24A	0.9600
C8—H8	0.9800	C24—H24B	0.9600
C9—C11	1.526 (4)	C24—H24C	0.9600
C9—C10	1.564 (4)	C25—H25A	0.9600
C9—H9	0.9800	C25—H25B	0.9600
C10—C18	1.537 (4)	C25—H25C	0.9600
C11—C12	1.536 (4)	C27—H27A	0.9700
C11—H11A	0.9700	C27—H27B	0.9700
C26—O1—C3	115.8 (2)	C12—C13—C17	116.1 (2)
C7—O2—H2	109.5	C14—C13—C17	101.4 (2)
C26—O4—C27	114.9 (3)	C15—C14—C8	120.8 (2)
C23—O6—C24	115.8 (3)	C15—C14—C13	103.4 (2)
C2—C1—C10	115.6 (2)	C8—C14—C13	113.8 (2)
C2—C1—H1A	108.4	C15—C14—H14	105.9
C10—C1—H1A	108.4	C8—C14—H14	105.9
C2—C1—H1B	108.4	C13—C14—H14	105.9
C10—C1—H1B	108.4	C14—C15—C16	104.6 (2)
H1A—C1—H1B	107.4	C14—C15—H15A	110.8
C3—C2—C1	109.2 (2)	C16—C15—H15A	110.8
C3—C2—H2A	109.9	C14—C15—H15B	110.8
C1—C2—H2A	109.9	C16—C15—H15B	110.8
C3—C2—H2B	109.9	H15A—C15—H15B	108.9
C1—C2—H2B	109.9	C15—C16—C17	107.5 (2)
H2A—C2—H2B	108.3	C15—C16—H16A	110.2
O1—C3—C2	107.9 (2)	C17—C16—H16A	110.2
O1—C3—C4	109.2 (2)	C15—C16—H16B	110.2
C2—C3—C4	111.0 (2)	C17—C16—H16B	110.2
O1—C3—H3	109.6	H16A—C16—H16B	108.5
C2—C3—H3	109.6	C20—C17—C13	119.8 (2)
C4—C3—H3	109.6	C20—C17—C16	112.6 (2)
C3—C4—C5	112.7 (2)	C13—C17—C16	102.8 (2)
C3—C4—H4A	109.0	C20—C17—H17	107.0
C5—C4—H4A	109.0	C13—C17—H17	107.0
C3—C4—H4B	109.0	C16—C17—H17	107.0
C5—C4—H4B	109.0	C10—C18—H18A	109.5
H4A—C4—H4B	107.8	C10—C18—H18B	109.5
C6—C5—C4	110.8 (2)	H18A—C18—H18B	109.5
C6—C5—C10	112.0 (2)	C10—C18—H18C	109.5
C4—C5—C10	113.3 (2)	H18A—C18—H18C	109.5
C6—C5—H5	106.8	H18B—C18—H18C	109.5
C4—C5—H5	106.8	C13—C19—H19A	109.5
C10—C5—H5	106.8	C13—C19—H19B	109.5
C5—C6—C7	113.5 (2)	H19A—C19—H19B	109.5
C5—C6—H6A	108.9	C13—C19—H19C	109.5
C7—C6—H6A	108.9	H19A—C19—H19C	109.5
C5—C6—H6B	108.9	H19B—C19—H19C	109.5
C7—C6—H6B	108.9	C25—C20—C21	110.3 (3)
H6A—C6—H6B	107.7	C25—C20—C17	113.6 (3)
O2—C7—C6	105.9 (2)	C21—C20—C17	109.7 (2)
O2—C7—C8	112.7 (2)	C25—C20—H20	107.7
C6—C7—C8	111.3 (2)	C21—C20—H20	107.7
O2—C7—H7	108.9	C17—C20—H20	107.7
C6—C7—H7	108.9	C22—C21—C20	114.7 (2)
C8—C7—H7	108.9	C22—C21—H21A	108.6
C7—C8—C14	113.6 (2)	C20—C21—H21A	108.6
C7—C8—C9	109.8 (2)	C22—C21—H21B	108.6
C14—C8—C9	109.4 (2)	C20—C21—H21B	108.6
C7—C8—H8	107.9	H21A—C21—H21B	107.6
C14—C8—H8	107.9	C23—C22—C21	113.7 (3)
C9—C8—H8	107.9	C23—C22—H22A	108.8
C11—C9—C8	112.2 (2)	C21—C22—H22A	108.8
C11—C9—C10	112.5 (2)	C23—C22—H22B	108.8
C8—C9—C10	113.4 (2)	C21—C22—H22B	108.8
C11—C9—H9	106.0	H22A—C22—H22B	107.7
C8—C9—H9	106.0	O5—C23—O6	122.6 (3)
C10—C9—H9	106.0	O5—C23—C22	125.6 (3)
C18—C10—C1	106.7 (2)	O6—C23—C22	111.7 (3)
C18—C10—C5	109.3 (2)	O6—C24—H24A	109.5
C1—C10—C5	107.8 (2)	O6—C24—H24B	109.5
C18—C10—C9	111.0 (2)	H24A—C24—H24B	109.5
C1—C10—C9	112.7 (2)	O6—C24—H24C	109.5
C5—C10—C9	109.3 (2)	H24A—C24—H24C	109.5
C9—C11—C12	114.0 (2)	H24B—C24—H24C	109.5
C9—C11—H11A	108.7	C20—C25—H25A	109.5
C12—C11—H11A	108.7	C20—C25—H25B	109.5
C9—C11—H11B	108.7	H25A—C25—H25B	109.5
C12—C11—H11B	108.7	C20—C25—H25C	109.5
H11A—C11—H11B	107.6	H25A—C25—H25C	109.5
C13—C12—C11	111.1 (2)	H25B—C25—H25C	109.5
C13—C12—H12A	109.4	O3—C26—O1	128.4 (3)
C11—C12—H12A	109.4	O3—C26—O4	125.3 (3)
C13—C12—H12B	109.4	O1—C26—O4	106.3 (3)
C11—C12—H12B	109.4	O4—C27—Cl1	110.7 (2)
H12A—C12—H12B	108.0	O4—C27—H27A	109.5
C19—C13—C12	110.1 (2)	Cl1—C27—H27A	109.5
C19—C13—C14	111.5 (2)	O4—C27—H27B	109.5
C12—C13—C14	107.7 (2)	Cl1—C27—H27B	109.5
C19—C13—C17	109.7 (2)	H27A—C27—H27B	108.1
C10—C1—C2—C3	57.9 (3)	C11—C12—C13—C14	56.6 (3)
C26—O1—C3—C2	−156.1 (2)	C11—C12—C13—C17	169.4 (2)
C26—O1—C3—C4	83.2 (3)	C7—C8—C14—C15	−56.4 (3)
C1—C2—C3—O1	−176.6 (2)	C9—C8—C14—C15	−179.6 (2)
C1—C2—C3—C4	−57.1 (3)	C7—C8—C14—C13	179.6 (2)
O1—C3—C4—C5	175.3 (2)	C9—C8—C14—C13	56.4 (3)
C2—C3—C4—C5	56.5 (3)	C19—C13—C14—C15	−71.7 (3)
C3—C4—C5—C6	−179.9 (2)	C12—C13—C14—C15	167.4 (2)
C3—C4—C5—C10	−53.1 (3)	C17—C13—C14—C15	45.0 (3)
C4—C5—C6—C7	72.7 (3)	C19—C13—C14—C8	61.2 (3)
C10—C5—C6—C7	−54.9 (3)	C12—C13—C14—C8	−59.7 (3)
C5—C6—C7—O2	178.7 (2)	C17—C13—C14—C8	177.9 (2)
C5—C6—C7—C8	55.9 (3)	C8—C14—C15—C16	−161.5 (3)
O2—C7—C8—C14	63.5 (3)	C13—C14—C15—C16	−32.8 (3)
C6—C7—C8—C14	−177.7 (2)	C14—C15—C16—C17	8.1 (3)
O2—C7—C8—C9	−173.5 (2)	C19—C13—C17—C20	−46.8 (3)
C6—C7—C8—C9	−54.7 (3)	C12—C13—C17—C20	78.8 (3)
C7—C8—C9—C11	−175.7 (2)	C14—C13—C17—C20	−164.8 (2)
C14—C8—C9—C11	−50.3 (3)	C19—C13—C17—C16	79.0 (3)
C7—C8—C9—C10	55.5 (3)	C12—C13—C17—C16	−155.4 (2)
C14—C8—C9—C10	−179.1 (2)	C14—C13—C17—C16	−39.0 (3)
C2—C1—C10—C18	−170.0 (2)	C15—C16—C17—C20	149.8 (3)
C2—C1—C10—C5	−52.7 (3)	C15—C16—C17—C13	19.5 (3)
C2—C1—C10—C9	67.9 (3)	C13—C17—C20—C25	−56.5 (4)
C6—C5—C10—C18	−69.4 (3)	C16—C17—C20—C25	−177.5 (3)
C4—C5—C10—C18	164.4 (2)	C13—C17—C20—C21	179.5 (3)
C6—C5—C10—C1	175.0 (2)	C16—C17—C20—C21	58.5 (3)
C4—C5—C10—C1	48.8 (3)	C25—C20—C21—C22	65.9 (4)
C6—C5—C10—C9	52.2 (3)	C17—C20—C21—C22	−168.2 (3)
C4—C5—C10—C9	−74.0 (3)	C20—C21—C22—C23	−172.9 (3)
C11—C9—C10—C18	−62.0 (3)	C24—O6—C23—O5	1.0 (5)
C8—C9—C10—C18	66.7 (3)	C24—O6—C23—C22	−178.4 (3)
C11—C9—C10—C1	57.7 (3)	C21—C22—C23—O5	−0.9 (5)
C8—C9—C10—C1	−173.7 (2)	C21—C22—C23—O6	178.5 (3)
C11—C9—C10—C5	177.5 (2)	C3—O1—C26—O3	5.0 (5)
C8—C9—C10—C5	−53.9 (3)	C3—O1—C26—O4	−175.2 (2)
C8—C9—C11—C12	51.3 (3)	C27—O4—C26—O3	1.9 (5)
C10—C9—C11—C12	−179.4 (2)	C27—O4—C26—O1	−177.9 (2)
C9—C11—C12—C13	−55.0 (3)	C26—O4—C27—Cl1	82.3 (3)
C11—C12—C13—C19	−65.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O2i	0.97	2.49	3.339 (4)	146
C27—H27B···O5ii	0.97	2.40	3.270 (4)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯O2i	0.97	2.49	3.339 (4)	146
C27—H27B⋯O5ii	0.97	2.40	3.270 (4)	149

Symmetry codes: (i) ; (ii) .