Selective solvent inclusion as a tool for mapping molecular properties in crystal structures: a diethylstilbestrol example

Useful information about hydrogen bonding, the preferred modes of hydrophobic interaction and conformational preferences of a specific molecule can be obtained from cocrystallization of the solute with a selected series of solvent molecules. This method is used in a study of nine different crystal structures of diethylstilbestrol (DES) solvates. It is shown that solvent inclusion results not only in stronger hydrogen bonds, but usually also in a larger number of favorable C—H...π interactions between DES molecules. Furthermore, solvent molecules such as DMSO, DMF, acetonitrile and acetone demonstrate important hydrogen-bond donating properties in addition to their more familiar role as hydrogen-bond acceptors. Molecular conformations in the crystal structures compare favorably with results from molecular mechanics calculations.

Computing details

For all compounds, data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 1997).

Figures

Fig.1:

(dacn) diethylstilbestrol acetonitrile solvate (1/1)

Crystal data

C18H20O2·C2H3N	Z = 2
Mr = 309.39	F(000) = 332
Triclinic, P1	Dx = 1.212 Mg m^−3
a = 7.5866 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9294 (2) Å	Cell parameters from 6167 reflections
c = 13.4851 (3) Å	θ = 2.4–41.1°
α = 95.762 (1)°	µ = 0.08 mm^−1
β = 106.263 (1)°	T = 150 K
γ = 101.386 (1)°	Needle, colourless
V = 847.87 (3) Å^3	1.25 × 0.45 × 0.20 mm

Data collection

Siemens SMART CCD diffractometer	10110 independent reflections
Radiation source: fine-focus sealed tube	7526 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
Detector resolution: 8.3 pixels mm^-1	θmax = 41.2°, θmin = 2.4°
Sets of exposures each taken over 0.6° ω rotation scans	h = −12→13
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996)	k = −16→15
Tmin = 0.907, Tmax = 0.985	l = −24→24
19304 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0811P)^2 + 0.1642P] where P = (Fo^2 + 2Fc^2)/3
10110 reflections	(Δ/σ)max = 0.011
230 parameters	Δρmax = 0.69 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

Special details

Refinement. Refinement of F² against ALL reflections.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1A	0.80471 (11)	0.05204 (9)	0.03300 (5)	0.03023 (14)
H1A	0.730 (2)	−0.0501 (19)	−0.0024 (13)	0.045*
C1A	0.74945 (9)	0.13852 (8)	0.33342 (5)	0.01556 (10)
C2A	0.87550 (10)	0.24142 (8)	0.29887 (5)	0.01867 (11)
H2A	0.9517 (10)	0.3381 (12)	0.3457 (6)	0.022*
C3A	0.89547 (11)	0.20990 (9)	0.19940 (6)	0.02185 (12)
H3A	0.9879 (12)	0.2830 (10)	0.1774 (3)	0.026*
C4A	0.78470 (11)	0.07521 (9)	0.13150 (5)	0.02121 (12)
C5A	0.65768 (11)	−0.02917 (9)	0.16350 (5)	0.02128 (12)
H5A	0.5808 (10)	−0.1245 (13)	0.1162 (6)	0.026*
C6A	0.64092 (10)	0.00315 (8)	0.26342 (5)	0.01894 (11)
H6A	0.5497 (11)	−0.0717 (9)	0.2857 (3)	0.023*
C7A	0.72353 (9)	0.17162 (7)	0.43879 (5)	0.01476 (10)
C8A	0.51935 (9)	0.16027 (8)	0.43479 (5)	0.01754 (11)
H81A	0.51354 (11)	0.1810 (2)	0.5068 (6)	0.021*
H82A	0.4457 (6)	0.0538 (9)	0.4040 (3)	0.021*
C9A	0.42856 (12)	0.27288 (11)	0.37117 (7)	0.02610 (15)
H91A	0.2959 (12)	0.2553 (7)	0.3675 (6)	0.039*
H92A	0.4385 (11)	0.2562 (7)	0.3007 (6)	0.039*
H93A	0.4934 (10)	0.3789 (9)	0.4048 (5)	0.039*
O1'A	0.77319 (11)	0.31509 (9)	0.93152 (5)	0.03122 (14)
H1'A	0.800 (2)	0.233 (2)	0.9634 (13)	0.047*
C1'A	0.84593 (9)	0.23464 (7)	0.63501 (5)	0.01509 (10)
C2'A	0.77289 (10)	0.35838 (8)	0.66465 (5)	0.01849 (11)
H2'A	0.7368 (5)	0.4258 (9)	0.6155 (6)	0.022*
C3'A	0.75125 (11)	0.38611 (9)	0.76397 (6)	0.02132 (12)
H3'A	0.7006 (7)	0.4732 (12)	0.7828 (3)	0.026*
C4'A	0.80259 (11)	0.28827 (9)	0.83614 (5)	0.02093 (12)
C5'A	0.88035 (11)	0.16689 (9)	0.80941 (5)	0.02108 (12)
H5'A	0.9190 (5)	0.1008 (9)	0.8594 (7)	0.025*
C6'A	0.90207 (10)	0.14142 (8)	0.71040 (5)	0.01812 (11)
H6'A	0.9580 (7)	0.0562 (11)	0.6928 (2)	0.022*
C7'A	0.86972 (9)	0.20164 (7)	0.52907 (5)	0.01440 (9)
C8'A	1.07068 (9)	0.19920 (8)	0.53269 (5)	0.01702 (10)
H83A	1.07172 (9)	0.1578 (4)	0.4612 (6)	0.020*
H84A	1.1169 (4)	0.1275 (6)	0.5810 (4)	0.020*
C9'A	1.20546 (11)	0.35973 (10)	0.56983 (7)	0.02472 (14)
H94A	1.3346 (11)	0.35091 (18)	0.5758 (7)	0.037*
H95A	1.2001 (9)	0.4032 (6)	0.6383 (7)	0.037*
H96A	1.1679 (8)	0.4279 (7)	0.5192 (5)	0.037*
N1B	0.59120 (18)	0.74419 (13)	0.92432 (8)	0.0447 (2)
C1B	0.47328 (19)	0.63215 (13)	0.89979 (7)	0.0376 (2)
C2B	0.3256 (2)	0.49062 (14)	0.87176 (9)	0.0452 (3)
H21B	0.3808 (7)	0.4005 (10)	0.8622 (9)	0.068*
H22B	0.2287 (14)	0.4937 (6)	0.8056 (9)	0.068*
H23B	0.2663 (13)	0.4809 (7)	0.9283 (8)	0.068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0429 (4)	0.0369 (3)	0.0161 (2)	0.0134 (3)	0.0141 (2)	0.0056 (2)
C1A	0.0159 (2)	0.0181 (2)	0.0137 (2)	0.00521 (18)	0.00495 (18)	0.00371 (18)
C2A	0.0196 (3)	0.0213 (3)	0.0161 (2)	0.0040 (2)	0.0069 (2)	0.0047 (2)
C3A	0.0243 (3)	0.0268 (3)	0.0178 (3)	0.0065 (2)	0.0098 (2)	0.0077 (2)
C4A	0.0261 (3)	0.0275 (3)	0.0141 (2)	0.0121 (2)	0.0078 (2)	0.0058 (2)
C5A	0.0254 (3)	0.0225 (3)	0.0156 (2)	0.0070 (2)	0.0055 (2)	0.0014 (2)
C6A	0.0203 (3)	0.0199 (3)	0.0162 (2)	0.0044 (2)	0.0054 (2)	0.0024 (2)
C7A	0.0154 (2)	0.0160 (2)	0.0142 (2)	0.00481 (17)	0.00557 (18)	0.00380 (17)
C8A	0.0152 (2)	0.0212 (3)	0.0172 (2)	0.00429 (19)	0.00593 (19)	0.0054 (2)
C9A	0.0204 (3)	0.0328 (4)	0.0317 (4)	0.0126 (3)	0.0106 (3)	0.0153 (3)
O1'A	0.0458 (4)	0.0361 (3)	0.0195 (2)	0.0143 (3)	0.0188 (3)	0.0052 (2)
C1'A	0.0158 (2)	0.0169 (2)	0.0138 (2)	0.00487 (18)	0.00555 (18)	0.00301 (17)
C2'A	0.0224 (3)	0.0186 (3)	0.0186 (3)	0.0082 (2)	0.0097 (2)	0.0052 (2)
C3'A	0.0269 (3)	0.0206 (3)	0.0209 (3)	0.0087 (2)	0.0124 (2)	0.0030 (2)
C4'A	0.0241 (3)	0.0247 (3)	0.0157 (2)	0.0055 (2)	0.0094 (2)	0.0024 (2)
C5'A	0.0252 (3)	0.0261 (3)	0.0150 (2)	0.0096 (2)	0.0075 (2)	0.0066 (2)
C6'A	0.0214 (3)	0.0208 (3)	0.0150 (2)	0.0088 (2)	0.0065 (2)	0.00489 (19)
C7'A	0.0156 (2)	0.0156 (2)	0.0136 (2)	0.00535 (17)	0.00544 (17)	0.00319 (17)
C8'A	0.0162 (2)	0.0200 (3)	0.0161 (2)	0.00653 (19)	0.00547 (19)	0.00296 (19)
C9'A	0.0192 (3)	0.0259 (3)	0.0263 (3)	0.0007 (2)	0.0079 (2)	−0.0017 (3)
N1B	0.0637 (7)	0.0452 (5)	0.0292 (4)	0.0245 (5)	0.0127 (4)	0.0051 (4)
C1B	0.0593 (7)	0.0387 (5)	0.0210 (3)	0.0267 (5)	0.0113 (4)	0.0059 (3)
C2B	0.0696 (8)	0.0390 (5)	0.0279 (4)	0.0234 (5)	0.0087 (5)	0.0065 (4)

Geometric parameters (Å, º)

O1A—C4A	1.3785 (9)	C1'A—C2'A	1.4017 (9)
O1A—H1A	0.970 (17)	C1'A—C6'A	1.4054 (9)
C1A—C2A	1.4015 (9)	C1'A—C7'A	1.4971 (8)
C1A—C6A	1.4046 (10)	C2'A—C3'A	1.3981 (9)
C1A—C7A	1.4967 (8)	C2'A—H2'A	0.9589
C2A—C3A	1.3987 (9)	C3'A—C4'A	1.3981 (11)
C2A—H2A	0.9835	C3'A—H3'A	0.9744
C3A—C4A	1.3928 (11)	C4'A—C5'A	1.3950 (11)
C3A—H3A	0.9904	C5'A—C6'A	1.3923 (9)
C4A—C5A	1.3939 (11)	C5'A—H5'A	0.9623
C5A—C6A	1.3954 (10)	C6'A—H6'A	0.9814
C5A—H5A	0.9786	C7'A—C8'A	1.5162 (9)
C6A—H6A	0.9949	C8'A—C9'A	1.5301 (10)
C7A—C7'A	1.3583 (9)	C8'A—H83A	1.0007
C7A—C8A	1.5175 (9)	C8'A—H84A	1.0007
C8A—C9A	1.5288 (10)	C9'A—H94A	0.9800
C8A—H81A	0.9846	C9'A—H95A	0.9800
C8A—H82A	0.9846	C9'A—H96A	0.9800
C9A—H91A	0.9739	N1B—C1B	1.1511 (17)
C9A—H92A	0.9739	C1B—C2B	1.4503 (19)
C9A—H93A	0.9739	C2B—H21B	0.9910
O1'A—C4'A	1.3717 (9)	C2B—H22B	0.9910
O1'A—H1'A	0.915 (18)	C2B—H23B	0.9910
C4A—O1A—H1A	108.2 (10)	C3'A—C2'A—C1'A	121.73 (6)
C2A—C1A—C6A	117.37 (6)	C3'A—C2'A—H2'A	119.1
C2A—C1A—C7A	122.34 (6)	C1'A—C2'A—H2'A	119.1
C6A—C1A—C7A	120.26 (6)	C4'A—C3'A—C2'A	119.67 (6)
C3A—C2A—C1A	121.58 (7)	C4'A—C3'A—H3'A	120.2
C3A—C2A—H2A	119.2	C2'A—C3'A—H3'A	120.2
C1A—C2A—H2A	119.2	O1'A—C4'A—C5'A	122.10 (7)
C4A—C3A—C2A	119.66 (7)	O1'A—C4'A—C3'A	118.29 (7)
C4A—C3A—H3A	120.2	C5'A—C4'A—C3'A	119.62 (6)
C2A—C3A—H3A	120.2	C6'A—C5'A—C4'A	119.98 (6)
O1A—C4A—C3A	117.49 (7)	C6'A—C5'A—H5'A	120.0
O1A—C4A—C5A	122.43 (7)	C4'A—C5'A—H5'A	120.0
C3A—C4A—C5A	120.08 (6)	C5'A—C6'A—C1'A	121.68 (6)
C4A—C5A—C6A	119.55 (7)	C5'A—C6'A—H6'A	119.2
C4A—C5A—H5A	120.2	C1'A—C6'A—H6'A	119.2
C6A—C5A—H5A	120.2	C7A—C7'A—C1'A	122.97 (6)
C5A—C6A—C1A	121.75 (6)	C7A—C7'A—C8'A	123.44 (6)
C5A—C6A—H6A	119.1	C1'A—C7'A—C8'A	113.55 (5)
C1A—C6A—H6A	119.1	C7'A—C8'A—C9'A	112.60 (6)
C7'A—C7A—C1A	122.36 (6)	C7'A—C8'A—H83A	109.1
C7'A—C7A—C8A	123.84 (6)	C9'A—C8'A—H83A	109.1
C1A—C7A—C8A	113.73 (5)	C7'A—C8'A—H84A	109.1
C7A—C8A—C9A	113.34 (6)	C9'A—C8'A—H84A	109.1
C7A—C8A—H81A	108.9	H83A—C8'A—H84A	107.8
C9A—C8A—H81A	108.9	C8'A—C9'A—H94A	109.5
C7A—C8A—H82A	108.9	C8'A—C9'A—H95A	109.5
C9A—C8A—H82A	108.9	H94A—C9'A—H95A	109.5
H81A—C8A—H82A	107.7	C8'A—C9'A—H96A	109.5
C8A—C9A—H91A	109.5	H94A—C9'A—H96A	109.5
C8A—C9A—H92A	109.5	H95A—C9'A—H96A	109.5
H91A—C9A—H92A	109.5	N1B—C1B—C2B	178.50 (11)
C8A—C9A—H93A	109.5	C1B—C2B—H21B	109.5
H91A—C9A—H93A	109.5	C1B—C2B—H22B	109.5
H92A—C9A—H93A	109.5	H21B—C2B—H22B	109.5
C4'A—O1'A—H1'A	105.2 (11)	C1B—C2B—H23B	109.5
C2'A—C1'A—C6'A	117.27 (6)	H21B—C2B—H23B	109.5
C2'A—C1'A—C7'A	122.90 (5)	H22B—C2B—H23B	109.5
C6'A—C1'A—C7'A	119.81 (6)
C6A—C1A—C2A—C3A	−1.10 (10)	C1'A—C2'A—C3'A—C4'A	−0.27 (12)
C7A—C1A—C2A—C3A	−178.83 (6)	C2'A—C3'A—C4'A—O1'A	−177.64 (7)
C1A—C2A—C3A—C4A	1.63 (11)	C2'A—C3'A—C4'A—C5'A	1.99 (12)
C2A—C3A—C4A—O1A	177.73 (7)	O1'A—C4'A—C5'A—C6'A	178.02 (7)
C2A—C3A—C4A—C5A	−1.42 (11)	C3'A—C4'A—C5'A—C6'A	−1.60 (12)
O1A—C4A—C5A—C6A	−178.38 (7)	C4'A—C5'A—C6'A—C1'A	−0.54 (12)
C3A—C4A—C5A—C6A	0.72 (11)	C2'A—C1'A—C6'A—C5'A	2.19 (11)
C4A—C5A—C6A—C1A	−0.21 (11)	C7'A—C1'A—C6'A—C5'A	−179.21 (7)
C2A—C1A—C6A—C5A	0.38 (10)	C1A—C7A—C7'A—C1'A	−179.88 (6)
C7A—C1A—C6A—C5A	178.17 (6)	C8A—C7A—C7'A—C1'A	−3.10 (10)
C2A—C1A—C7A—C7'A	−56.41 (9)	C1A—C7A—C7'A—C8'A	−2.21 (10)
C6A—C1A—C7A—C7'A	125.92 (7)	C8A—C7A—C7'A—C8'A	174.57 (6)
C2A—C1A—C7A—C8A	126.51 (7)	C2'A—C1'A—C7'A—C7A	−59.13 (9)
C6A—C1A—C7A—C8A	−51.16 (8)	C6'A—C1'A—C7'A—C7A	122.35 (7)
C7'A—C7A—C8A—C9A	123.02 (7)	C2'A—C1'A—C7'A—C8'A	122.99 (7)
C1A—C7A—C8A—C9A	−59.96 (8)	C6'A—C1'A—C7'A—C8'A	−55.53 (8)
C6'A—C1'A—C2'A—C3'A	−1.78 (11)	C7A—C7'A—C8'A—C9'A	113.05 (7)
C7'A—C1'A—C2'A—C3'A	179.66 (6)	C1'A—C7'A—C8'A—C9'A	−69.08 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···N1B^i	0.970 (17)	1.935 (17)	2.9037 (14)	176.8 (15)
O1′A—H1′A···O1A^ii	0.915 (18)	1.950 (18)	2.8515 (10)	168.4 (16)

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

(ddmso) diethylstilbestrol dimethylsulfoxide solvate (1/1)

Crystal data

C18H20O2·C2H6OS	Z = 2
Mr = 346.47	F(000) = 372
Triclinic, P1	Dx = 1.242 Mg m^−3
a = 7.8841 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1401 (5) Å	Cell parameters from 5718 reflections
c = 13.6505 (8) Å	θ = 2.3–37.9°
α = 90.975 (2)°	µ = 0.19 mm^−1
β = 105.924 (2)°	T = 150 K
γ = 100.892 (2)°	Needle, colourless
V = 926.41 (9) Å^3	0.75 × 0.35 × 0.15 mm

Data collection

Siemens SMART CCD diffractometer	8871 independent reflections
Radiation source: fine-focus sealed tube	7444 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
Detector resolution: 8.3 pixels mm^-1	θmax = 38.0°, θmin = 2.3°
Sets of exposures each taken over 0.3° ω rotation scans	h = −12→13
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996)	k = −15→15
Tmin = 0.868, Tmax = 0.972	l = −22→23
14256 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0658P)^2 + 0.1723P] where P = (Fo^2 + 2Fc^2)/3
8871 reflections	(Δ/σ)max = 0.012
241 parameters	Δρmax = 0.54 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

Special details

Refinement. Refinement of F² against ALL reflections.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1A	0.17303 (9)	0.11935 (8)	0.91369 (5)	0.02410 (11)
H1A	0.095 (2)	0.1741 (17)	0.9150 (12)	0.036*
C1A	0.32910 (9)	0.17555 (8)	0.64429 (5)	0.01653 (11)
C2A	0.23378 (10)	0.27392 (8)	0.67516 (5)	0.01905 (12)
H2A	0.2035 (4)	0.3555 (11)	0.6330 (6)	0.023*
C3A	0.18111 (10)	0.25809 (9)	0.76462 (6)	0.02015 (12)
H3A	0.1141 (9)	0.3271 (9)	0.7840 (3)	0.024*
C4A	0.22511 (10)	0.14272 (9)	0.82615 (5)	0.01841 (12)
C5A	0.32598 (11)	0.04701 (9)	0.79942 (6)	0.02062 (12)
H5A	0.3599 (5)	−0.0298 (11)	0.8424 (6)	0.025*
C6A	0.37698 (10)	0.06406 (9)	0.70969 (6)	0.01943 (12)
H6A	0.4476 (9)	−0.0030 (9)	0.6919 (2)	0.023*
C7A	0.37820 (9)	0.18665 (8)	0.54601 (5)	0.01615 (11)
C8A	0.57349 (10)	0.18239 (9)	0.55545 (6)	0.01948 (12)
H81A	0.58827 (17)	0.17430 (12)	0.4879 (6)	0.023*
H82B	0.6017 (3)	0.0943 (8)	0.5886 (3)	0.023*
C9A	0.70720 (12)	0.31914 (13)	0.61528 (8)	0.03227 (19)
H91A	0.8279 (12)	0.3077 (5)	0.6200 (7)	0.048*
H92B	0.6933 (10)	0.3284 (7)	0.6828 (7)	0.048*
H93C	0.6845 (9)	0.4072 (9)	0.5807 (5)	0.048*
O1'A	0.43964 (9)	0.24780 (8)	0.08184 (5)	0.02637 (12)
H1'A	0.354 (2)	0.1904 (18)	0.0323 (13)	0.040*
C1'A	0.30326 (9)	0.20581 (8)	0.35734 (5)	0.01625 (11)
C2'A	0.43690 (10)	0.32269 (8)	0.34443 (6)	0.01912 (12)
H2'A	0.4991 (9)	0.3946 (10)	0.3998 (8)	0.023*
C3'A	0.48075 (10)	0.33607 (9)	0.25239 (6)	0.02057 (12)
H3'A	0.5754 (13)	0.4187 (11)	0.24548 (11)	0.025*
C4'A	0.39012 (10)	0.23207 (9)	0.17016 (5)	0.01892 (12)
C5'A	0.25476 (10)	0.11557 (9)	0.18031 (6)	0.01981 (12)
H5'A	0.1937 (9)	0.0466 (10)	0.1260 (8)	0.024*
C6'A	0.21219 (10)	0.10379 (8)	0.27274 (5)	0.01883 (12)
H6'A	0.1148 (13)	0.0210 (11)	0.27903 (10)	0.023*
C7'A	0.25389 (9)	0.19111 (8)	0.45543 (5)	0.01637 (11)
C8'A	0.05348 (10)	0.17480 (9)	0.44258 (6)	0.01997 (12)
H83A	0.0299 (2)	0.1523 (2)	0.5078 (6)	0.024*
H84B	−0.0117 (6)	0.0904 (8)	0.3934 (5)	0.024*
C9'A	−0.01909 (13)	0.31426 (12)	0.40619 (8)	0.02932 (17)
H94A	−0.1499 (12)	0.2946 (4)	0.3956 (7)	0.044*
H95B	0.0076 (12)	0.3398 (7)	0.3417 (7)	0.044*
H96C	0.0384 (11)	0.3978 (8)	0.4580 (6)	0.044*
S1B	0.79897 (3)	0.26260 (2)	−0.021144 (17)	0.02585 (6)
O1B	0.95990 (11)	0.29463 (9)	−0.06415 (7)	0.03634 (17)
C1B	0.88274 (14)	0.33704 (13)	0.10853 (8)	0.03238 (19)
H11B	0.9681 (13)	0.2816 (9)	0.1459 (4)	0.049*
H12B	0.7848 (9)	0.3297 (11)	0.1383 (4)	0.049*
H13B	0.9403 (14)	0.4398 (10)	0.11110 (10)	0.049*
C2B	0.66923 (14)	0.39785 (13)	−0.07177 (8)	0.03256 (19)
H21B	0.6202 (12)	0.3773 (7)	−0.1433 (7)	0.049*
H22B	0.7439 (8)	0.4944 (9)	−0.0580 (7)	0.049*
H23B	0.5745 (12)	0.3939 (8)	−0.0410 (7)	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0241 (3)	0.0349 (3)	0.0171 (2)	0.0095 (2)	0.00965 (19)	0.0039 (2)
C1A	0.0163 (3)	0.0192 (3)	0.0147 (2)	0.0050 (2)	0.00444 (19)	0.0005 (2)
C2A	0.0212 (3)	0.0212 (3)	0.0164 (3)	0.0080 (2)	0.0056 (2)	0.0013 (2)
C3A	0.0207 (3)	0.0243 (3)	0.0176 (3)	0.0086 (2)	0.0063 (2)	0.0004 (2)
C4A	0.0168 (3)	0.0243 (3)	0.0143 (2)	0.0043 (2)	0.0046 (2)	0.0004 (2)
C5A	0.0223 (3)	0.0244 (3)	0.0178 (3)	0.0086 (2)	0.0073 (2)	0.0046 (2)
C6A	0.0206 (3)	0.0230 (3)	0.0175 (3)	0.0088 (2)	0.0068 (2)	0.0030 (2)
C7A	0.0162 (3)	0.0182 (3)	0.0149 (2)	0.0053 (2)	0.00474 (19)	0.0005 (2)
C8A	0.0175 (3)	0.0249 (3)	0.0182 (3)	0.0082 (2)	0.0058 (2)	0.0015 (2)
C9A	0.0193 (3)	0.0409 (5)	0.0330 (4)	0.0016 (3)	0.0051 (3)	−0.0085 (4)
O1'A	0.0248 (3)	0.0387 (3)	0.0162 (2)	0.0031 (2)	0.00889 (19)	0.0025 (2)
C1'A	0.0163 (3)	0.0184 (3)	0.0145 (2)	0.0045 (2)	0.00435 (19)	0.0015 (2)
C2'A	0.0201 (3)	0.0194 (3)	0.0173 (3)	0.0020 (2)	0.0058 (2)	0.0004 (2)
C3'A	0.0208 (3)	0.0223 (3)	0.0183 (3)	0.0021 (2)	0.0065 (2)	0.0027 (2)
C4'A	0.0186 (3)	0.0245 (3)	0.0154 (3)	0.0068 (2)	0.0059 (2)	0.0034 (2)
C5'A	0.0201 (3)	0.0232 (3)	0.0155 (3)	0.0036 (2)	0.0046 (2)	−0.0008 (2)
C6'A	0.0185 (3)	0.0209 (3)	0.0161 (3)	0.0020 (2)	0.0048 (2)	0.0002 (2)
C7'A	0.0159 (3)	0.0182 (3)	0.0154 (2)	0.0038 (2)	0.00496 (19)	0.0011 (2)
C8'A	0.0157 (3)	0.0259 (3)	0.0182 (3)	0.0033 (2)	0.0050 (2)	0.0018 (2)
C9'A	0.0243 (4)	0.0377 (4)	0.0307 (4)	0.0155 (3)	0.0091 (3)	0.0094 (3)
S1B	0.02927 (11)	0.02513 (9)	0.02839 (10)	0.00920 (7)	0.01414 (8)	0.00440 (7)
O1B	0.0397 (4)	0.0421 (4)	0.0411 (4)	0.0184 (3)	0.0271 (3)	0.0080 (3)
C1B	0.0281 (4)	0.0457 (5)	0.0274 (4)	0.0120 (4)	0.0111 (3)	0.0049 (4)
C2B	0.0299 (4)	0.0396 (5)	0.0349 (4)	0.0145 (4)	0.0146 (3)	0.0139 (4)

Geometric parameters (Å, º)

O1A—C4A	1.3735 (9)	C1'A—C7'A	1.4950 (9)
O1A—H1A	0.869 (16)	C2'A—C3'A	1.3930 (10)
C1A—C2A	1.4025 (10)	C2'A—H2'A	0.9496
C1A—C6A	1.4033 (10)	C3'A—C4'A	1.3932 (11)
C1A—C7A	1.4949 (9)	C3'A—H3'A	0.9822
C2A—C3A	1.3950 (10)	C4'A—C5'A	1.3959 (11)
C2A—H2A	0.9752	C5'A—C6'A	1.3927 (10)
C3A—C4A	1.3951 (11)	C5'A—H5'A	0.9233
C3A—H3A	0.9709	C6'A—H6'A	0.9943
C4A—C5A	1.3937 (11)	C7'A—C8'A	1.5190 (10)
C5A—C6A	1.3925 (10)	C8'A—C9'A	1.5297 (12)
C5A—H5A	0.9525	C8'A—H83A	0.9762
C6A—H6A	0.9710	C8'A—H84B	0.9762
C7A—C7'A	1.3575 (10)	C9'A—H94A	0.9816
C7A—C8A	1.5174 (10)	C9'A—H95B	0.9817
C8A—C9A	1.5281 (13)	C9'A—H96C	0.9816
C8A—H81A	0.9634	S1B—O1B	1.5212 (8)
C8A—H82B	0.9634	S1B—C2B	1.7807 (10)
C9A—H91A	0.9613	S1B—C1B	1.7833 (11)
C9A—H92B	0.9613	C1B—H11B	0.9586
C9A—H93C	0.9613	C1B—H12B	0.9586
O1'A—C4'A	1.3674 (9)	C1B—H13B	0.9586
O1'A—H1'A	0.889 (17)	C2B—H21B	0.9478
C1'A—C2'A	1.4019 (10)	C2B—H22B	0.9478
C1'A—C6'A	1.4050 (10)	C2B—H23B	0.9478
C4A—O1A—H1A	108.4 (10)	C2'A—C3'A—H3'A	120.0
C2A—C1A—C6A	117.16 (6)	C4'A—C3'A—H3'A	120.0
C2A—C1A—C7A	122.23 (6)	O1'A—C4'A—C3'A	118.00 (7)
C6A—C1A—C7A	120.62 (6)	O1'A—C4'A—C5'A	122.27 (7)
C3A—C2A—C1A	121.73 (7)	C3'A—C4'A—C5'A	119.72 (7)
C3A—C2A—H2A	119.1	C6'A—C5'A—C4'A	119.71 (7)
C1A—C2A—H2A	119.1	C6'A—C5'A—H5'A	120.1
C2A—C3A—C4A	119.71 (7)	C4'A—C5'A—H5'A	120.1
C2A—C3A—H3A	120.1	C5'A—C6'A—C1'A	121.74 (7)
C4A—C3A—H3A	120.1	C5'A—C6'A—H6'A	119.1
O1A—C4A—C5A	117.94 (7)	C1'A—C6'A—H6'A	119.1
O1A—C4A—C3A	122.31 (7)	C7A—C7'A—C1'A	122.05 (6)
C5A—C4A—C3A	119.76 (7)	C7A—C7'A—C8'A	124.16 (6)
C6A—C5A—C4A	119.77 (7)	C1'A—C7'A—C8'A	113.73 (6)
C6A—C5A—H5A	120.1	C7'A—C8'A—C9'A	113.47 (7)
C4A—C5A—H5A	120.1	C7'A—C8'A—H83A	108.9
C5A—C6A—C1A	121.79 (7)	C9'A—C8'A—H83A	108.9
C5A—C6A—H6A	119.1	C7'A—C8'A—H84B	108.9
C1A—C6A—H6A	119.1	C9'A—C8'A—H84B	108.9
C7'A—C7A—C1A	121.92 (6)	H83A—C8'A—H84B	107.7
C7'A—C7A—C8A	123.37 (6)	C8'A—C9'A—H94A	109.5
C1A—C7A—C8A	114.60 (6)	C8'A—C9'A—H95B	109.5
C7A—C8A—C9A	113.90 (6)	H94A—C9'A—H95B	109.5
C7A—C8A—H81A	108.8	C8'A—C9'A—H96C	109.5
C9A—C8A—H81A	108.8	H94A—C9'A—H96C	109.5
C7A—C8A—H82B	108.8	H95B—C9'A—H96C	109.5
C9A—C8A—H82B	108.8	O1B—S1B—C2B	104.50 (5)
H81A—C8A—H82B	107.7	O1B—S1B—C1B	105.25 (5)
C8A—C9A—H91A	109.5	C2B—S1B—C1B	98.84 (5)
C8A—C9A—H92B	109.5	S1B—C1B—H11B	109.5
H91A—C9A—H92B	109.5	S1B—C1B—H12B	109.5
C8A—C9A—H93C	109.5	H11B—C1B—H12B	109.5
H91A—C9A—H93C	109.5	S1B—C1B—H13B	109.5
H92B—C9A—H93C	109.5	H11B—C1B—H13B	109.5
C4'A—O1'A—H1'A	107.9 (10)	H12B—C1B—H13B	109.5
C2'A—C1'A—C6'A	117.23 (6)	S1B—C2B—H21B	109.5
C2'A—C1'A—C7'A	122.14 (6)	S1B—C2B—H22B	109.5
C6'A—C1'A—C7'A	120.60 (6)	H21B—C2B—H22B	109.5
C3'A—C2'A—C1'A	121.67 (7)	S1B—C2B—H23B	109.5
C3'A—C2'A—H2'A	119.2	H21B—C2B—H23B	109.5
C1'A—C2'A—H2'A	119.2	H22B—C2B—H23B	109.5
C2'A—C3'A—C4'A	119.91 (7)
C6A—C1A—C2A—C3A	−2.89 (11)	C1'A—C2'A—C3'A—C4'A	0.35 (12)
C7A—C1A—C2A—C3A	176.85 (7)	C2'A—C3'A—C4'A—O1'A	−178.83 (7)
C1A—C2A—C3A—C4A	0.64 (12)	C2'A—C3'A—C4'A—C5'A	0.49 (11)
C2A—C3A—C4A—O1A	−178.33 (7)	O1'A—C4'A—C5'A—C6'A	178.91 (7)
C2A—C3A—C4A—C5A	1.94 (12)	C3'A—C4'A—C5'A—C6'A	−0.38 (11)
O1A—C4A—C5A—C6A	178.11 (7)	C4'A—C5'A—C6'A—C1'A	−0.58 (11)
C3A—C4A—C5A—C6A	−2.16 (12)	C2'A—C1'A—C6'A—C5'A	1.37 (11)
C4A—C5A—C6A—C1A	−0.20 (12)	C7'A—C1'A—C6'A—C5'A	179.57 (7)
C2A—C1A—C6A—C5A	2.67 (11)	C1A—C7A—C7'A—C1'A	178.54 (6)
C7A—C1A—C6A—C5A	−177.07 (7)	C8A—C7A—C7'A—C1'A	−5.51 (11)
C2A—C1A—C7A—C7'A	−52.18 (10)	C1A—C7A—C7'A—C8'A	−4.39 (11)
C6A—C1A—C7A—C7'A	127.54 (8)	C8A—C7A—C7'A—C8'A	171.56 (7)
C2A—C1A—C7A—C8A	131.54 (7)	C2'A—C1'A—C7'A—C7A	−54.86 (10)
C6A—C1A—C7A—C8A	−48.74 (9)	C6'A—C1'A—C7'A—C7A	127.04 (8)
C7'A—C7A—C8A—C9A	116.36 (8)	C2'A—C1'A—C7'A—C8'A	127.79 (7)
C1A—C7A—C8A—C9A	−67.42 (9)	C6'A—C1'A—C7'A—C8'A	−50.31 (9)
C6'A—C1'A—C2'A—C3'A	−1.26 (11)	C7A—C7'A—C8'A—C9'A	116.47 (8)
C7'A—C1'A—C2'A—C3'A	−179.42 (7)	C1'A—C7'A—C8'A—C9'A	−66.24 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O1B^i	0.869 (16)	1.738 (16)	2.6004 (10)	171.2 (16)
O1′A—H1′A···O1A^ii	0.889 (17)	1.852 (17)	2.7191 (9)	164.6 (15)

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

(ddmf) diethylstilbestrol N,N-dimethylformamide solvate (1/1)

Crystal data

C18H20O2·C3H7NO	Z = 2
Mr = 341.44	F(000) = 368
Triclinic, P1	Dx = 1.194 Mg m^−3
a = 7.6393 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.9833 (3) Å	Cell parameters from 5987 reflections
c = 13.3161 (1) Å	θ = 2.1–38.0°
α = 91.883 (2)°	µ = 0.08 mm^−1
β = 104.036 (1)°	T = 150 K
γ = 104.311 (1)°	Plate, colourless
V = 950.00 (3) Å^3	0.70 × 0.65 × 0.15 mm

Data collection

Siemens SMART CCD diffractometer	9040 independent reflections
Radiation source: fine-focus sealed tube	7209 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
Detector resolution: 8.3 pixels mm^-1	θmax = 38.0°, θmin = 2.1°
Sets of exposures each taken over 0.3° ω rotation scans	h = −12→12
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996)	k = −17→16
Tmin = 0.946, Tmax = 0.988	l = −22→22
14448 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0839P)^2 + 0.1252P] where P = (Fo^2 + 2Fc^2)/3
9040 reflections	(Δ/σ)max = 0.009
251 parameters	Δρmax = 0.50 e Å^−3
0 restraints	Δρmin = −0.31 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1A	0.59398 (9)	0.21122 (7)	0.91708 (4)	0.03045 (13)
H1A	0.610 (2)	0.1215 (16)	0.9166 (11)	0.046*
C1A	0.29205 (9)	0.28762 (7)	0.62698 (5)	0.01889 (11)
C2A	0.35322 (11)	0.16662 (7)	0.63835 (5)	0.02474 (13)
H2A	0.3227 (4)	0.0974 (8)	0.5760 (8)	0.030*
C3A	0.45560 (11)	0.13933 (8)	0.73396 (6)	0.02540 (13)
H3A	0.4964 (5)	0.0548 (11)	0.73975 (9)	0.030*
C4A	0.49859 (10)	0.23458 (7)	0.82096 (5)	0.02146 (11)
C5A	0.44276 (10)	0.35758 (7)	0.81130 (5)	0.02192 (12)
H5A	0.4761 (4)	0.4258 (8)	0.8713 (7)	0.026*
C6A	0.33921 (9)	0.38252 (7)	0.71556 (5)	0.02009 (11)
H6A	0.2977 (5)	0.4697 (10)	0.70985 (8)	0.024*
C7A	0.17017 (9)	0.31226 (7)	0.52662 (5)	0.01900 (11)
C8A	−0.01978 (10)	0.32404 (8)	0.53575 (5)	0.02287 (12)
H81A	−0.0880 (6)	0.3500 (2)	0.4691 (6)	0.027*
H82A	−0.00195 (18)	0.3992 (6)	0.5908 (5)	0.027*
C9A	−0.13776 (12)	0.18866 (10)	0.56176 (8)	0.03497 (18)
H91A	−0.2550 (12)	0.2034 (3)	0.5725 (7)	0.052*
H92A	−0.0674 (8)	0.1593 (6)	0.6256 (7)	0.052*
H93A	−0.1669 (11)	0.1160 (7)	0.5039 (6)	0.052*
O1'A	−0.22685 (11)	0.43255 (7)	0.05911 (5)	0.03747 (16)
H1'A	−0.300 (2)	0.3558 (18)	0.0199 (13)	0.056*
C1'A	0.10433 (9)	0.34757 (7)	0.33765 (5)	0.01956 (11)
C2'A	−0.06969 (10)	0.25545 (8)	0.28978 (5)	0.02305 (12)
H2'A	−0.1131 (5)	0.1702 (11)	0.3222 (4)	0.028*
C3'A	−0.18326 (10)	0.28155 (8)	0.19701 (5)	0.02474 (13)
H3'A	−0.3060 (15)	0.2166 (8)	0.1655 (4)	0.030*
C4'A	−0.12135 (11)	0.40040 (8)	0.14936 (5)	0.02479 (13)
C5'A	0.05289 (11)	0.49203 (8)	0.19457 (5)	0.02516 (13)
H5'A	0.0964 (6)	0.5731 (11)	0.1618 (4)	0.030*
C6'A	0.16345 (10)	0.46562 (7)	0.28733 (5)	0.02229 (12)
H6'A	0.2828 (15)	0.5294 (8)	0.3177 (4)	0.027*
C7'A	0.22714 (9)	0.32388 (7)	0.43787 (5)	0.01954 (11)
C8'A	0.42210 (10)	0.32064 (8)	0.43216 (5)	0.02412 (13)
H83A	0.5002 (7)	0.31891 (8)	0.5039 (6)	0.029*
H84A	0.4807 (5)	0.4075 (7)	0.4043 (2)	0.029*
C9'A	0.42217 (13)	0.19472 (11)	0.36309 (7)	0.03529 (18)
H94A	0.5498 (11)	0.2010 (5)	0.3583 (6)	0.053*
H95A	0.3413 (13)	0.1934 (6)	0.2935 (6)	0.053*
H96A	0.3754 (13)	0.1094 (7)	0.3934 (5)	0.053*
O1B	−0.34584 (11)	0.96623 (7)	−0.07092 (5)	0.03587 (14)
C1B	−0.24319 (13)	0.95866 (9)	0.01587 (7)	0.03018 (15)
H11A	−0.2234 (3)	1.0322 (10)	0.0701 (8)	0.036*
N1B	−0.15913 (12)	0.85932 (9)	0.04036 (7)	0.03512 (16)
C2B	−0.1871 (3)	0.74435 (14)	−0.03609 (13)	0.0687 (5)
H21B	−0.2879 (19)	0.7420 (9)	−0.0891 (9)	0.103*
H22B	−0.206 (2)	0.6638 (11)	−0.0061 (5)	0.103*
H23B	−0.0846 (16)	0.7554 (8)	−0.0608 (9)	0.103*
C3B	−0.04010 (15)	0.86109 (15)	0.14505 (11)	0.0519 (3)
H31B	−0.0382 (13)	0.9419 (11)	0.1878 (5)	0.078*
H32B	0.0857 (14)	0.8646 (13)	0.14099 (14)	0.078*
H33B	−0.0892 (11)	0.7779 (11)	0.1755 (5)	0.078*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0367 (3)	0.0322 (3)	0.0192 (2)	0.0124 (2)	−0.0029 (2)	0.00630 (19)
C1A	0.0208 (2)	0.0205 (2)	0.0151 (2)	0.00624 (19)	0.00317 (19)	0.00281 (18)
C2A	0.0328 (3)	0.0229 (3)	0.0181 (2)	0.0118 (2)	0.0015 (2)	0.0005 (2)
C3A	0.0318 (3)	0.0236 (3)	0.0209 (3)	0.0124 (2)	0.0017 (2)	0.0031 (2)
C4A	0.0221 (3)	0.0243 (3)	0.0169 (2)	0.0065 (2)	0.0022 (2)	0.0050 (2)
C5A	0.0261 (3)	0.0224 (3)	0.0156 (2)	0.0063 (2)	0.0024 (2)	0.00147 (19)
C6A	0.0239 (3)	0.0201 (3)	0.0166 (2)	0.0071 (2)	0.0044 (2)	0.00263 (18)
C7A	0.0210 (2)	0.0204 (2)	0.0153 (2)	0.00649 (19)	0.00282 (19)	0.00286 (18)
C8A	0.0227 (3)	0.0279 (3)	0.0199 (3)	0.0095 (2)	0.0056 (2)	0.0053 (2)
C9A	0.0253 (3)	0.0409 (4)	0.0374 (4)	0.0046 (3)	0.0084 (3)	0.0151 (3)
O1'A	0.0481 (4)	0.0340 (3)	0.0239 (3)	0.0169 (3)	−0.0091 (2)	0.0046 (2)
C1'A	0.0205 (2)	0.0234 (3)	0.0147 (2)	0.0067 (2)	0.00319 (19)	0.00285 (18)
C2'A	0.0224 (3)	0.0255 (3)	0.0185 (2)	0.0048 (2)	0.0016 (2)	0.0033 (2)
C3'A	0.0237 (3)	0.0277 (3)	0.0198 (3)	0.0075 (2)	−0.0004 (2)	0.0010 (2)
C4'A	0.0308 (3)	0.0271 (3)	0.0169 (2)	0.0143 (2)	0.0002 (2)	0.0015 (2)
C5'A	0.0318 (3)	0.0247 (3)	0.0195 (3)	0.0101 (2)	0.0045 (2)	0.0053 (2)
C6'A	0.0239 (3)	0.0238 (3)	0.0185 (2)	0.0059 (2)	0.0043 (2)	0.0036 (2)
C7'A	0.0198 (2)	0.0224 (3)	0.0156 (2)	0.00564 (19)	0.00267 (19)	0.00246 (18)
C8'A	0.0202 (3)	0.0326 (3)	0.0195 (3)	0.0078 (2)	0.0040 (2)	0.0038 (2)
C9'A	0.0333 (4)	0.0478 (5)	0.0285 (4)	0.0184 (4)	0.0079 (3)	−0.0029 (3)
O1B	0.0449 (4)	0.0352 (3)	0.0307 (3)	0.0160 (3)	0.0089 (3)	0.0138 (2)
C1B	0.0360 (4)	0.0294 (3)	0.0306 (3)	0.0145 (3)	0.0117 (3)	0.0102 (3)
N1B	0.0395 (4)	0.0369 (4)	0.0415 (4)	0.0207 (3)	0.0206 (3)	0.0211 (3)
C2B	0.1200 (14)	0.0431 (6)	0.0738 (9)	0.0480 (8)	0.0531 (10)	0.0211 (6)
C3B	0.0312 (4)	0.0713 (8)	0.0589 (7)	0.0180 (5)	0.0129 (4)	0.0417 (6)

Geometric parameters (Å, º)

O1A—C4A	1.3692 (8)	C2'A—C3'A	1.3999 (9)
O1A—H1A	0.934 (15)	C2'A—H2'A	0.9872
C1A—C2A	1.3990 (9)	C3'A—C4'A	1.3970 (11)
C1A—C6A	1.4037 (9)	C3'A—H3'A	0.9832
C1A—C7A	1.4982 (8)	C4'A—C5'A	1.3944 (11)
C2A—C3A	1.3971 (9)	C5'A—C6'A	1.3906 (9)
C2A—H2A	1.0043	C5'A—H5'A	0.9581
C3A—C4A	1.3939 (10)	C6'A—H6'A	0.9582
C3A—H3A	0.9683	C7'A—C8'A	1.5178 (10)
C4A—C5A	1.3960 (10)	C8'A—C9'A	1.5332 (12)
C5A—C6A	1.3936 (9)	C8'A—H83A	0.9999
C5A—H5A	0.9733	C8'A—H84A	0.9999
C6A—H6A	0.9970	C9'A—H94A	0.9791
C7A—C7'A	1.3539 (9)	C9'A—H95A	0.9791
C7A—C8A	1.5177 (10)	C9'A—H96A	0.9791
C8A—C9A	1.5293 (11)	O1B—C1B	1.2457 (10)
C8A—H81A	0.9920	C1B—N1B	1.3178 (11)
C8A—H82A	0.9920	C1B—H11A	0.9705
C9A—H91A	0.9850	N1B—C2B	1.4476 (17)
C9A—H92A	0.9850	N1B—C3B	1.4650 (14)
C9A—H93A	0.9850	C2B—H21B	0.9045
O1'A—C4'A	1.3712 (8)	C2B—H22B	0.9045
O1'A—H1'A	0.890 (17)	C2B—H23B	0.9045
C1'A—C2'A	1.4019 (10)	C3B—H31B	0.9677
C1'A—C6'A	1.4063 (9)	C3B—H32B	0.9677
C1'A—C7'A	1.4967 (8)	C3B—H33B	0.9677
C4A—O1A—H1A	111.0 (9)	C2'A—C3'A—H3'A	120.2
C2A—C1A—C6A	117.41 (6)	O1'A—C4'A—C5'A	117.76 (7)
C2A—C1A—C7A	121.96 (6)	O1'A—C4'A—C3'A	122.47 (7)
C6A—C1A—C7A	120.50 (6)	C5'A—C4'A—C3'A	119.76 (6)
C3A—C2A—C1A	121.84 (6)	C6'A—C5'A—C4'A	119.97 (7)
C3A—C2A—H2A	119.1	C6'A—C5'A—H5'A	120.0
C1A—C2A—H2A	119.1	C4'A—C5'A—H5'A	120.0
C4A—C3A—C2A	119.55 (6)	C5'A—C6'A—C1'A	121.62 (6)
C4A—C3A—H3A	120.2	C5'A—C6'A—H6'A	119.2
C2A—C3A—H3A	120.2	C1'A—C6'A—H6'A	119.2
O1A—C4A—C3A	121.96 (6)	C7A—C7'A—C1'A	122.34 (6)
O1A—C4A—C5A	118.26 (6)	C7A—C7'A—C8'A	123.33 (6)
C3A—C4A—C5A	119.78 (6)	C1'A—C7'A—C8'A	114.28 (5)
C6A—C5A—C4A	119.88 (6)	C7'A—C8'A—C9'A	112.82 (6)
C6A—C5A—H5A	120.1	C7'A—C8'A—H83A	109.0
C4A—C5A—H5A	120.1	C9'A—C8'A—H83A	109.0
C5A—C6A—C1A	121.50 (6)	C7'A—C8'A—H84A	109.0
C5A—C6A—H6A	119.2	C9'A—C8'A—H84A	109.0
C1A—C6A—H6A	119.2	H83A—C8'A—H84A	107.8
C7'A—C7A—C1A	122.56 (6)	C8'A—C9'A—H94A	109.5
C7'A—C7A—C8A	124.28 (6)	C8'A—C9'A—H95A	109.5
C1A—C7A—C8A	113.16 (5)	H94A—C9'A—H95A	109.5
C7A—C8A—C9A	112.41 (6)	C8'A—C9'A—H96A	109.5
C7A—C8A—H81A	109.1	H94A—C9'A—H96A	109.5
C9A—C8A—H81A	109.1	H95A—C9'A—H96A	109.5
C7A—C8A—H82A	109.1	O1B—C1B—N1B	125.62 (9)
C9A—C8A—H82A	109.1	O1B—C1B—H11A	117.2
H81A—C8A—H82A	107.9	N1B—C1B—H11A	117.2
C8A—C9A—H91A	109.5	C1B—N1B—C2B	119.98 (10)
C8A—C9A—H92A	109.5	C1B—N1B—C3B	121.10 (10)
H91A—C9A—H92A	109.5	C2B—N1B—C3B	118.90 (10)
C8A—C9A—H93A	109.5	N1B—C2B—H21B	109.5
H91A—C9A—H93A	109.5	N1B—C2B—H22B	109.5
H92A—C9A—H93A	109.5	H21B—C2B—H22B	109.5
C4'A—O1'A—H1'A	110.9 (11)	N1B—C2B—H23B	109.5
C2'A—C1'A—C6'A	117.45 (6)	H21B—C2B—H23B	109.5
C2'A—C1'A—C7'A	122.72 (6)	H22B—C2B—H23B	109.5
C6'A—C1'A—C7'A	119.82 (6)	N1B—C3B—H31B	109.5
C3'A—C2'A—C1'A	121.50 (6)	N1B—C3B—H32B	109.5
C3'A—C2'A—H2'A	119.2	H31B—C3B—H32B	109.5
C1'A—C2'A—H2'A	119.3	N1B—C3B—H33B	109.5
C4'A—C3'A—C2'A	119.68 (7)	H31B—C3B—H33B	109.5
C4'A—C3'A—H3'A	120.2	H32B—C3B—H33B	109.5
C6A—C1A—C2A—C3A	0.69 (11)	C2'A—C3'A—C4'A—O1'A	−179.26 (7)
C7A—C1A—C2A—C3A	−175.32 (7)	C2'A—C3'A—C4'A—C5'A	−0.03 (11)
C1A—C2A—C3A—C4A	0.06 (12)	O1'A—C4'A—C5'A—C6'A	178.61 (7)
C2A—C3A—C4A—O1A	178.15 (7)	C3'A—C4'A—C5'A—C6'A	−0.66 (11)
C2A—C3A—C4A—C5A	−1.44 (11)	C4'A—C5'A—C6'A—C1'A	0.09 (11)
O1A—C4A—C5A—C6A	−177.55 (6)	C2'A—C1'A—C6'A—C5'A	1.13 (10)
C3A—C4A—C5A—C6A	2.06 (11)	C7'A—C1'A—C6'A—C5'A	−179.47 (6)
C4A—C5A—C6A—C1A	−1.31 (11)	C1A—C7A—C7'A—C1'A	179.59 (6)
C2A—C1A—C6A—C5A	−0.06 (10)	C8A—C7A—C7'A—C1'A	−1.09 (10)
C7A—C1A—C6A—C5A	176.01 (6)	C1A—C7A—C7'A—C8'A	−3.24 (10)
C2A—C1A—C7A—C7'A	−63.18 (10)	C8A—C7A—C7'A—C8'A	176.07 (6)
C6A—C1A—C7A—C7'A	120.93 (7)	C2'A—C1'A—C7'A—C7A	−59.21 (10)
C2A—C1A—C7A—C8A	117.43 (7)	C6'A—C1'A—C7'A—C7A	121.42 (8)
C6A—C1A—C7A—C8A	−58.46 (8)	C2'A—C1'A—C7'A—C8'A	123.39 (7)
C7'A—C7A—C8A—C9A	115.91 (8)	C6'A—C1'A—C7'A—C8'A	−55.98 (8)
C1A—C7A—C8A—C9A	−64.71 (8)	C7A—C7'A—C8'A—C9'A	115.42 (8)
C6'A—C1'A—C2'A—C3'A	−1.83 (10)	C1'A—C7'A—C8'A—C9'A	−67.21 (8)
C7'A—C1'A—C2'A—C3'A	178.78 (6)	O1B—C1B—N1B—C2B	−1.79 (16)
C1'A—C2'A—C3'A—C4'A	1.31 (11)	O1B—C1B—N1B—C3B	179.62 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O1B^i	0.934 (15)	1.671 (15)	2.6009 (9)	173.6 (14)
O1′A—H1′A···O1A^ii	0.890 (17)	1.836 (18)	2.7032 (10)	164.2 (16)

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

(dactn) diethylstilbestrol acetone solvate (1/1)

Crystal data

C18H20O2·C3H6O	Z = 4
Mr = 326.42	F(000) = 704
Triclinic, P1	Dx = 1.169 Mg m^−3
a = 9.6266 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.662 (2) Å	Cell parameters from 4011 reflections
c = 15.365 (2) Å	θ = 1.8–27.8°
α = 69.979 (2)°	µ = 0.08 mm^−1
β = 77.853 (2)°	T = 150 K
γ = 83.927 (3)°	Needle, colourless
V = 1854.9 (5) Å^3	0.75 × 0.30 × 0.15 mm

Data collection

Siemens SMART CCD diffractometer	7676 independent reflections
Radiation source: fine-focus sealed tube	5236 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 8.3 pixels mm^-1	θmax = 27.9°, θmin = 1.8°
Sets of exposures each taken over 0.3° ω rotation scans	h = −12→11
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996)	k = −17→17
Tmin = 0.943, Tmax = 0.989	l = −19→19
15681 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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0426P)^2 + 1.2036P] where P = (Fo^2 + 2Fc^2)/3
7676 reflections	(Δ/σ)max = 0.010
480 parameters	Δρmax = 0.39 e Å^−3
6 restraints	Δρmin = −0.30 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1A	0.42768 (18)	1.42829 (11)	0.38618 (12)	0.0382 (4)
H1A	0.516 (3)	1.445 (2)	0.3619 (19)	0.057*
C1A	0.3411 (2)	1.14626 (14)	0.35979 (12)	0.0232 (4)
C2A	0.2470 (2)	1.19288 (15)	0.41781 (14)	0.0284 (4)
H2A	0.158 (2)	1.1593 (8)	0.4530 (8)	0.034*
C3A	0.2770 (2)	1.28635 (16)	0.42652 (15)	0.0313 (5)
H3A	0.2097 (16)	1.3175 (8)	0.4682 (10)	0.038*
C4A	0.4023 (2)	1.33516 (15)	0.37605 (14)	0.0278 (4)
C5A	0.4967 (2)	1.29186 (15)	0.31652 (14)	0.0282 (4)
H5A	0.584 (2)	1.3266 (8)	0.2803 (8)	0.034*
C6A	0.4654 (2)	1.19883 (15)	0.30893 (13)	0.0250 (4)
H6A	0.5322 (15)	1.1689 (7)	0.2667 (9)	0.030*
C7A	0.31291 (19)	1.04568 (14)	0.34891 (13)	0.0224 (4)
C8A	0.3104 (2)	1.05499 (15)	0.24803 (13)	0.0250 (4)
H81A	0.3071 (2)	0.9840 (10)	0.24421 (14)	0.030*
H82A	0.3998 (13)	1.0866 (5)	0.2068 (6)	0.030*
C9A	0.1830 (2)	1.12149 (16)	0.21145 (15)	0.0339 (5)
H91A	0.1919 (8)	1.1318 (9)	0.1430 (9)	0.051*
H92A	0.1808 (9)	1.1907 (10)	0.2204 (9)	0.051*
H93A	0.0932 (12)	1.0853 (7)	0.2471 (8)	0.051*
O1'A	0.20749 (17)	0.57674 (11)	0.36821 (11)	0.0355 (4)
H1'A	0.288 (3)	0.533 (2)	0.3742 (18)	0.053*
C1'A	0.27272 (19)	0.85474 (14)	0.41046 (12)	0.0229 (4)
C2'A	0.1548 (2)	0.84183 (15)	0.37559 (13)	0.0269 (4)
H2'A	0.0846 (16)	0.9001 (13)	0.3602 (4)	0.032*
C3'A	0.1343 (2)	0.74936 (15)	0.36224 (14)	0.0292 (4)
H3'A	0.0520 (19)	0.7428 (2)	0.3378 (6)	0.035*
C4'A	0.2318 (2)	0.66623 (15)	0.38392 (13)	0.0261 (4)
C5'A	0.3479 (2)	0.67542 (15)	0.42100 (13)	0.0267 (4)
H5'A	0.4164 (16)	0.6162 (13)	0.4378 (4)	0.032*
C6'A	0.3669 (2)	0.76851 (15)	0.43426 (13)	0.0249 (4)
H6'A	0.4494 (18)	0.77398 (19)	0.4613 (6)	0.030*
C7'A	0.29847 (19)	0.95558 (14)	0.42196 (13)	0.0227 (4)
C8'A	0.3119 (2)	0.94565 (16)	0.52133 (13)	0.0291 (4)
H83A	0.3439 (5)	1.0135 (10)	0.52094 (13)	0.035*
H84A	0.3871 (12)	0.8905 (8)	0.5422 (3)	0.035*
C9'A	0.1729 (3)	0.9175 (2)	0.59213 (15)	0.0447 (6)
H94A	0.1889 (5)	0.9086 (13)	0.6563 (9)	0.067*
H95A	0.1392 (11)	0.8514 (12)	0.5917 (8)	0.067*
H96A	0.1000 (12)	0.9743 (10)	0.5745 (7)	0.067*
O1B	0.43950 (17)	1.44769 (12)	0.87736 (12)	0.0413 (4)
H1B	0.364 (3)	1.483 (2)	0.8914 (19)	0.062*
C1B	0.3487 (2)	1.16402 (14)	0.85797 (13)	0.0244 (4)
C2B	0.2465 (2)	1.21591 (15)	0.90718 (14)	0.0300 (4)
H2B	0.153 (2)	1.1848 (7)	0.9374 (7)	0.036*
C3B	0.2734 (2)	1.31067 (16)	0.91451 (15)	0.0328 (5)
H3B	0.2027 (18)	1.3444 (9)	0.9485 (9)	0.039*
C4B	0.4042 (2)	1.35565 (15)	0.87174 (14)	0.0291 (4)
C5B	0.5070 (2)	1.30556 (15)	0.82223 (14)	0.0288 (4)
H5B	0.600 (2)	1.3367 (7)	0.7923 (7)	0.035*
C6B	0.4790 (2)	1.21201 (15)	0.81501 (13)	0.0262 (4)
H6B	0.5518 (17)	1.1783 (8)	0.7790 (8)	0.031*
C7B	0.32507 (19)	1.06151 (15)	0.84939 (13)	0.0241 (4)
C8B	0.3322 (2)	1.06463 (15)	0.74867 (13)	0.0277 (4)
H81B	0.3327 (2)	0.9935 (11)	0.74777 (13)	0.033*
H82B	0.4210 (13)	1.0955 (5)	0.7099 (6)	0.033*
C9B	0.2072 (3)	1.12736 (18)	0.70598 (15)	0.0395 (5)
H91B	0.2201 (9)	1.1313 (10)	0.6387 (10)	0.059*
H92B	0.2034 (10)	1.1992 (10)	0.7095 (10)	0.059*
H93B	0.1168 (13)	1.0925 (8)	0.7419 (8)	0.059*
O1'B	0.21795 (16)	0.57480 (11)	0.91247 (11)	0.0357 (4)
H1'B	0.138 (3)	0.574 (2)	0.8973 (18)	0.053*
C1'B	0.2841 (2)	0.87097 (14)	0.91567 (12)	0.0234 (4)
C2'B	0.1658 (2)	0.85323 (15)	0.88447 (14)	0.0270 (4)
H2'B	0.0977 (16)	0.9111 (13)	0.8641 (5)	0.032*
C3'B	0.1420 (2)	0.75629 (15)	0.88150 (14)	0.0284 (4)
H3'B	0.0589 (19)	0.7459 (3)	0.8595 (5)	0.034*
C4'B	0.2381 (2)	0.67422 (14)	0.91017 (13)	0.0246 (4)
C5'B	0.3579 (2)	0.68934 (15)	0.94036 (13)	0.0257 (4)
H5'B	0.4254 (16)	0.6327 (13)	0.9590 (5)	0.031*
C6'B	0.3794 (2)	0.78662 (15)	0.94345 (13)	0.0246 (4)
H6'B	0.4632 (18)	0.7966 (3)	0.9656 (5)	0.029*
C7'B	0.30558 (19)	0.97376 (15)	0.92435 (13)	0.0244 (4)
C8'B	0.3050 (2)	0.96821 (15)	1.02484 (13)	0.0275 (4)
H83B	0.3224 (4)	1.0378 (10)	1.02519 (13)	0.033*
H84B	0.3830 (12)	0.9205 (7)	1.0485 (4)	0.033*
C9'B	0.1646 (2)	0.93059 (19)	1.09063 (15)	0.0397 (5)
H94B	0.1694 (6)	0.9275 (12)	1.1538 (9)	0.060*
H95B	0.1474 (9)	0.8619 (11)	1.0910 (8)	0.060*
H96B	0.0879 (11)	0.9785 (9)	1.0688 (7)	0.060*
O1C	−0.04119 (19)	0.56950 (16)	0.87920 (14)	0.0658 (6)
C1C	−0.1285 (3)	0.5233 (2)	0.86203 (16)	0.0451 (6)
C2C	−0.0943 (3)	0.4219 (2)	0.84627 (18)	0.0606 (8)
H21C	0.0073 (18)	0.4067 (8)	0.8412 (14)	0.091*
H22C	−0.123 (2)	0.4251 (5)	0.7884 (12)	0.091*
H23C	−0.1450 (18)	0.3675 (10)	0.8989 (11)	0.091*
C3C	−0.2717 (3)	0.5702 (2)	0.85520 (15)	0.0598 (8)
H31C	−0.2794 (3)	0.6349 (3)	0.8679 (2)	0.090*
H32C	−0.3406 (3)	0.5235 (3)	0.9004 (2)	0.090*
H33C	−0.2890 (3)	0.58296 (11)	0.79289 (16)	0.090*
O11D	0.71717 (14)	0.44720 (11)	0.31892 (10)	0.0557 (6)	0.893 (4)
C11D	0.80835 (15)	0.46646 (11)	0.35400 (9)	0.0397 (6)	0.893 (4)
C21D	0.80231 (15)	0.56113 (10)	0.38040 (10)	0.0634 (10)	0.893 (4)
H21D	0.71634 (14)	0.60093 (10)	0.36732 (10)	0.095*	0.893 (4)
H22D	0.88277 (16)	0.60240 (10)	0.34463 (11)	0.095*	0.893 (4)
H23D	0.80390 (15)	0.54168 (10)	0.44642 (10)	0.095*	0.893 (4)
C31D	0.9359 (3)	0.3937 (2)	0.3683 (2)	0.0532 (8)	0.893 (4)
H31D	0.9517 (13)	0.3563 (13)	0.3233 (12)	0.080*	0.893 (4)
H32D	0.9198 (10)	0.3442 (14)	0.4319 (12)	0.080*	0.893 (4)
H33D	1.0189 (16)	0.4334 (7)	0.3588 (14)	0.080*	0.893 (4)
O12D	0.6856 (6)	0.4858 (11)	0.3429 (12)	0.055*	0.107 (4)
C12D	0.80835 (15)	0.46646 (11)	0.35400 (9)	0.036*	0.107 (4)
C22D	0.8828 (18)	0.5302 (13)	0.3892 (17)	0.063*	0.107 (4)
H24D	0.8265	0.5945	0.3884	0.095*	0.107 (4)
H25D	0.9762	0.5476	0.3487	0.095*	0.107 (4)
H26D	0.8950	0.4908	0.4539	0.095*	0.107 (4)
C32D	0.8764 (19)	0.3629 (9)	0.3521 (17)	0.053*	0.107 (4)
H34D	0.8165	0.3284	0.3279	0.080*	0.107 (4)
H35D	0.8868	0.3192	0.4161	0.080*	0.107 (4)
H36D	0.9703	0.3735	0.3111	0.080*	0.107 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0444 (9)	0.0255 (8)	0.0542 (10)	0.0012 (7)	−0.0163 (8)	−0.0217 (7)
C1A	0.0277 (10)	0.0220 (10)	0.0214 (9)	0.0026 (8)	−0.0088 (7)	−0.0077 (8)
C2A	0.0312 (11)	0.0265 (11)	0.0292 (10)	0.0001 (8)	−0.0050 (8)	−0.0120 (9)
C3A	0.0346 (11)	0.0310 (11)	0.0337 (11)	0.0069 (9)	−0.0091 (9)	−0.0181 (9)
C4A	0.0366 (11)	0.0197 (10)	0.0328 (11)	0.0036 (8)	−0.0181 (9)	−0.0106 (8)
C5A	0.0312 (11)	0.0235 (10)	0.0305 (10)	−0.0011 (8)	−0.0105 (8)	−0.0069 (8)
C6A	0.0284 (10)	0.0241 (10)	0.0243 (9)	0.0029 (8)	−0.0069 (8)	−0.0101 (8)
C7A	0.0221 (9)	0.0225 (10)	0.0244 (9)	0.0019 (7)	−0.0057 (7)	−0.0100 (8)
C8A	0.0308 (10)	0.0231 (10)	0.0231 (9)	0.0005 (8)	−0.0063 (8)	−0.0099 (8)
C9A	0.0436 (12)	0.0309 (11)	0.0308 (11)	0.0055 (9)	−0.0160 (9)	−0.0113 (9)
O1'A	0.0393 (9)	0.0250 (8)	0.0478 (9)	0.0003 (6)	−0.0135 (7)	−0.0164 (7)
C1'A	0.0252 (10)	0.0223 (10)	0.0202 (9)	−0.0014 (8)	−0.0033 (7)	−0.0062 (8)
C2'A	0.0271 (10)	0.0220 (10)	0.0323 (10)	0.0024 (8)	−0.0088 (8)	−0.0086 (8)
C3'A	0.0286 (10)	0.0281 (11)	0.0334 (11)	−0.0019 (8)	−0.0117 (8)	−0.0095 (9)
C4'A	0.0312 (10)	0.0200 (10)	0.0269 (10)	−0.0025 (8)	−0.0029 (8)	−0.0088 (8)
C5'A	0.0278 (10)	0.0221 (10)	0.0288 (10)	0.0042 (8)	−0.0058 (8)	−0.0079 (8)
C6'A	0.0255 (10)	0.0259 (10)	0.0235 (9)	−0.0005 (8)	−0.0059 (7)	−0.0076 (8)
C7'A	0.0230 (9)	0.0228 (10)	0.0242 (9)	0.0012 (7)	−0.0068 (7)	−0.0092 (8)
C8'A	0.0389 (11)	0.0262 (10)	0.0251 (10)	−0.0015 (9)	−0.0113 (8)	−0.0088 (8)
C9'A	0.0583 (15)	0.0490 (14)	0.0271 (11)	−0.0153 (12)	0.0015 (10)	−0.0146 (10)
O1B	0.0326 (8)	0.0290 (8)	0.0720 (11)	−0.0002 (7)	−0.0133 (8)	−0.0270 (8)
C1B	0.0268 (10)	0.0216 (10)	0.0257 (10)	0.0016 (8)	−0.0082 (8)	−0.0080 (8)
C2B	0.0279 (10)	0.0260 (11)	0.0375 (11)	−0.0010 (8)	−0.0043 (8)	−0.0134 (9)
C3B	0.0293 (11)	0.0309 (11)	0.0431 (12)	0.0052 (9)	−0.0065 (9)	−0.0204 (10)
C4B	0.0317 (11)	0.0218 (10)	0.0393 (11)	0.0024 (8)	−0.0142 (9)	−0.0136 (9)
C5B	0.0266 (10)	0.0269 (11)	0.0326 (11)	−0.0026 (8)	−0.0068 (8)	−0.0083 (9)
C6B	0.0278 (10)	0.0243 (10)	0.0264 (10)	0.0031 (8)	−0.0046 (8)	−0.0097 (8)
C7B	0.0237 (9)	0.0231 (10)	0.0276 (10)	0.0024 (8)	−0.0063 (7)	−0.0110 (8)
C8B	0.0335 (11)	0.0241 (10)	0.0255 (10)	0.0006 (8)	−0.0050 (8)	−0.0091 (8)
C9B	0.0509 (14)	0.0358 (12)	0.0350 (12)	0.0077 (10)	−0.0197 (10)	−0.0117 (10)
O1'B	0.0324 (8)	0.0233 (8)	0.0572 (10)	0.0004 (6)	−0.0130 (7)	−0.0184 (7)
C1'B	0.0274 (10)	0.0223 (10)	0.0208 (9)	−0.0002 (8)	−0.0042 (7)	−0.0080 (8)
C2'B	0.0279 (10)	0.0222 (10)	0.0338 (11)	0.0060 (8)	−0.0127 (8)	−0.0107 (8)
C3'B	0.0270 (10)	0.0283 (11)	0.0349 (11)	0.0013 (8)	−0.0119 (8)	−0.0140 (9)
C4'B	0.0275 (10)	0.0210 (10)	0.0263 (10)	−0.0010 (8)	−0.0034 (7)	−0.0097 (8)
C5'B	0.0254 (10)	0.0219 (10)	0.0276 (10)	0.0023 (8)	−0.0049 (8)	−0.0064 (8)
C6'B	0.0237 (10)	0.0261 (10)	0.0242 (9)	−0.0013 (8)	−0.0056 (7)	−0.0078 (8)
C7'B	0.0236 (9)	0.0238 (10)	0.0282 (10)	0.0019 (8)	−0.0072 (7)	−0.0112 (8)
C8'B	0.0344 (11)	0.0254 (10)	0.0267 (10)	−0.0011 (8)	−0.0098 (8)	−0.0110 (8)
C9'B	0.0481 (14)	0.0476 (14)	0.0280 (11)	−0.0112 (11)	−0.0015 (9)	−0.0187 (10)
O1C	0.0455 (11)	0.0838 (14)	0.0701 (13)	−0.0245 (10)	−0.0206 (9)	−0.0155 (11)
C1C	0.0403 (13)	0.0575 (16)	0.0319 (12)	−0.0176 (12)	−0.0095 (10)	−0.0015 (11)
C2C	0.0678 (19)	0.071 (2)	0.0344 (14)	−0.0078 (15)	−0.0027 (12)	−0.0087 (13)
C3C	0.0454 (15)	0.0580 (17)	0.0660 (18)	−0.0141 (13)	−0.0236 (13)	0.0036 (14)
O11D	0.0480 (12)	0.0586 (14)	0.0690 (14)	−0.0113 (10)	−0.0209 (10)	−0.0232 (11)
C11D	0.0407 (14)	0.0406 (15)	0.0329 (13)	−0.0170 (12)	−0.0049 (10)	−0.0025 (11)
C21D	0.072 (2)	0.0519 (19)	0.069 (2)	−0.0192 (17)	0.0108 (18)	−0.0330 (17)
C31D	0.0469 (17)	0.0586 (19)	0.0405 (15)	−0.0010 (14)	−0.0016 (13)	−0.0031 (14)

Geometric parameters (Å, º)

O1A—C4A	1.386 (2)	C6B—H6B	0.9758
O1A—H1A	0.87 (3)	C7B—C7'B	1.345 (3)
C1A—C2A	1.396 (3)	C7B—C8B	1.521 (3)
C1A—C6A	1.400 (3)	C8B—C9B	1.530 (3)
C1A—C7A	1.498 (3)	C8B—H81B	0.9765
C2A—C3A	1.394 (3)	C8B—H82B	0.9765
C2A—H2A	0.9744	C9B—H91B	0.9976
C3A—C4A	1.387 (3)	C9B—H92B	0.9976
C3A—H3A	0.9821	C9B—H93B	0.9976
C4A—C5A	1.385 (3)	O1'B—C4'B	1.380 (2)
C5A—C6A	1.385 (3)	O1'B—H1'B	0.85 (3)
C5A—H5A	0.9762	C1'B—C2'B	1.397 (3)
C6A—H6A	0.9764	C1'B—C6'B	1.399 (3)
C7A—C7'A	1.349 (3)	C1'B—C7'B	1.495 (3)
C7A—C8A	1.516 (2)	C2'B—C3'B	1.385 (3)
C8A—C9A	1.533 (3)	C2'B—H2'B	0.9799
C8A—H81A	0.9953	C3'B—C4'B	1.386 (3)
C8A—H82A	0.9953	C3'B—H3'B	0.9719
C9A—H91A	0.9985	C4'B—C5'B	1.389 (3)
C9A—H92A	0.9985	C5'B—C6'B	1.385 (3)
C9A—H93A	0.9985	C5'B—H5'B	0.9611
O1'A—C4'A	1.376 (2)	C6'B—H6'B	0.9779
O1'A—H1'A	0.93 (3)	C7'B—C8'B	1.518 (3)
C1'A—C6'A	1.401 (3)	C8'B—C9'B	1.526 (3)
C1'A—C2'A	1.403 (3)	C8'B—H83B	0.9853
C1'A—C7'A	1.499 (3)	C8'B—H84B	0.9853
C2'A—C3'A	1.387 (3)	C9'B—H94B	0.9678
C2'A—H2'A	0.9850	C9'B—H95B	0.9678
C3'A—C4'A	1.389 (3)	C9'B—H96B	0.9678
C3'A—H3'A	0.9691	O1C—C1C	1.222 (3)
C4'A—C5'A	1.391 (3)	C1C—C3C	1.466 (3)
C5'A—C6'A	1.391 (3)	C1C—C2C	1.478 (4)
C5'A—H5'A	0.9858	C2C—H21C	0.9710
C6'A—H6'A	0.9918	C2C—H22C	0.9710
C7'A—C8'A	1.518 (2)	C2C—H23C	0.9710
C8'A—C9'A	1.527 (3)	C3C—H31C	0.9597
C8'A—H83A	1.0054	C3C—H32C	0.9597
C8'A—H84A	1.0054	C3C—H33C	0.9597
C9'A—H94A	0.9943	O11D—C11D	1.2146
C9'A—H95A	0.9943	C11D—C21D	1.4745
C9'A—H96A	0.9943	C11D—C31D	1.500 (3)
O1B—C4B	1.371 (2)	C21D—H21D	0.9596
O1B—H1B	0.86 (3)	C21D—H22D	0.9596
C1B—C2B	1.396 (3)	C21D—H23D	0.9596
C1B—C6B	1.403 (3)	C31D—H31D	0.9707
C1B—C7B	1.496 (3)	C31D—H32D	0.9707
C2B—C3B	1.392 (3)	C31D—H33D	0.9707
C2B—H2B	0.9845	C22D—H24D	0.9800
C3B—C4B	1.391 (3)	C22D—H25D	0.9800
C3B—H3B	0.9468	C22D—H26D	0.9800
C4B—C5B	1.386 (3)	C32D—H34D	0.9800
C5B—C6B	1.379 (3)	C32D—H35D	0.9800
C5B—H5B	0.9808	C32D—H36D	0.9800
C4A—O1A—H1A	110.3 (18)	C5B—C4B—C3B	119.65 (18)
C2A—C1A—C6A	117.05 (17)	C6B—C5B—C4B	120.03 (19)
C2A—C1A—C7A	123.02 (17)	C6B—C5B—H5B	120.0
C6A—C1A—C7A	119.92 (17)	C4B—C5B—H5B	120.0
C3A—C2A—C1A	121.48 (19)	C5B—C6B—C1B	121.80 (19)
C3A—C2A—H2A	119.3	C5B—C6B—H6B	119.1
C1A—C2A—H2A	119.3	C1B—C6B—H6B	119.1
C4A—C3A—C2A	119.69 (19)	C7'B—C7B—C1B	122.40 (17)
C4A—C3A—H3A	120.2	C7'B—C7B—C8B	123.41 (17)
C2A—C3A—H3A	120.2	C1B—C7B—C8B	114.13 (16)
C5A—C4A—O1A	121.86 (19)	C7B—C8B—C9B	112.45 (17)
C5A—C4A—C3A	120.23 (18)	C7B—C8B—H81B	109.1
O1A—C4A—C3A	117.90 (18)	C9B—C8B—H81B	109.1
C6A—C5A—C4A	119.29 (19)	C7B—C8B—H82B	109.1
C6A—C5A—H5A	120.4	C9B—C8B—H82B	109.1
C4A—C5A—H5A	120.4	H81B—C8B—H82B	107.8
C5A—C6A—C1A	122.24 (19)	C8B—C9B—H91B	109.5
C5A—C6A—H6A	118.9	C8B—C9B—H92B	109.5
C1A—C6A—H6A	118.9	H91B—C9B—H92B	109.5
C7'A—C7A—C1A	122.31 (16)	C8B—C9B—H93B	109.5
C7'A—C7A—C8A	124.21 (17)	H91B—C9B—H93B	109.5
C1A—C7A—C8A	113.40 (15)	H92B—C9B—H93B	109.5
C7A—C8A—C9A	112.61 (16)	C4'B—O1'B—H1'B	108.8 (18)
C7A—C8A—H81A	109.1	C2'B—C1'B—C6'B	117.29 (17)
C9A—C8A—H81A	109.1	C2'B—C1'B—C7'B	122.07 (17)
C7A—C8A—H82A	109.1	C6'B—C1'B—C7'B	120.56 (17)
C9A—C8A—H82A	109.1	C3'B—C2'B—C1'B	121.94 (18)
H81A—C8A—H82A	107.8	C3'B—C2'B—H2'B	119.0
C8A—C9A—H91A	109.5	C1'B—C2'B—H2'B	119.0
C8A—C9A—H92A	109.5	C2'B—C3'B—C4'B	119.28 (18)
H91A—C9A—H92A	109.5	C2'B—C3'B—H3'B	120.4
C8A—C9A—H93A	109.5	C4'B—C3'B—H3'B	120.4
H91A—C9A—H93A	109.5	O1'B—C4'B—C3'B	122.24 (17)
H92A—C9A—H93A	109.5	O1'B—C4'B—C5'B	117.38 (17)
C4'A—O1'A—H1'A	108.9 (16)	C3'B—C4'B—C5'B	120.36 (18)
C6'A—C1'A—C2'A	116.85 (17)	C6'B—C5'B—C4'B	119.56 (18)
C6'A—C1'A—C7'A	120.91 (16)	C6'B—C5'B—H5'B	120.2
C2'A—C1'A—C7'A	122.24 (17)	C4'B—C5'B—H5'B	120.2
C3'A—C2'A—C1'A	121.86 (18)	C5'B—C6'B—C1'B	121.56 (18)
C3'A—C2'A—H2'A	119.1	C5'B—C6'B—H6'B	119.2
C1'A—C2'A—H2'A	119.1	C1'B—C6'B—H6'B	119.2
C2'A—C3'A—C4'A	119.90 (18)	C7B—C7'B—C1'B	122.44 (17)
C2'A—C3'A—H3'A	120.1	C7B—C7'B—C8'B	124.15 (17)
C4'A—C3'A—H3'A	120.1	C1'B—C7'B—C8'B	113.41 (16)
O1'A—C4'A—C3'A	117.59 (17)	C7'B—C8'B—C9'B	112.34 (16)
O1'A—C4'A—C5'A	122.68 (18)	C7'B—C8'B—H83B	109.1
C3'A—C4'A—C5'A	119.73 (18)	C9'B—C8'B—H83B	109.1
C6'A—C5'A—C4'A	119.71 (18)	C7'B—C8'B—H84B	109.1
C6'A—C5'A—H5'A	120.1	C9'B—C8'B—H84B	109.1
C4'A—C5'A—H5'A	120.1	H83B—C8'B—H84B	107.9
C5'A—C6'A—C1'A	121.89 (18)	C8'B—C9'B—H94B	109.5
C5'A—C6'A—H6'A	119.1	C8'B—C9'B—H95B	109.5
C1'A—C6'A—H6'A	119.1	H94B—C9'B—H95B	109.5
C7A—C7'A—C1'A	122.16 (16)	C8'B—C9'B—H96B	109.5
C7A—C7'A—C8'A	123.78 (17)	H94B—C9'B—H96B	109.5
C1'A—C7'A—C8'A	114.03 (16)	H95B—C9'B—H96B	109.5
C7'A—C8'A—C9'A	112.89 (17)	O1C—C1C—C3C	119.3 (3)
C7'A—C8'A—H83A	109.0	O1C—C1C—C2C	122.2 (3)
C9'A—C8'A—H83A	109.0	C3C—C1C—C2C	118.4 (2)
C7'A—C8'A—H84A	109.0	C1C—C2C—H21C	109.5
C9'A—C8'A—H84A	109.0	C1C—C2C—H22C	109.5
H83A—C8'A—H84A	107.8	H21C—C2C—H22C	109.5
C8'A—C9'A—H94A	109.5	C1C—C2C—H23C	109.5
C8'A—C9'A—H95A	109.5	H21C—C2C—H23C	109.5
H94A—C9'A—H95A	109.5	H22C—C2C—H23C	109.5
C8'A—C9'A—H96A	109.5	C1C—C3C—H31C	109.5
H94A—C9'A—H96A	109.5	C1C—C3C—H32C	109.5
H95A—C9'A—H96A	109.5	H31C—C3C—H32C	109.5
C4B—O1B—H1B	110.1 (19)	C1C—C3C—H33C	109.5
C2B—C1B—C6B	117.24 (18)	H31C—C3C—H33C	109.5
C2B—C1B—C7B	123.23 (17)	H32C—C3C—H33C	109.5
C6B—C1B—C7B	119.53 (17)	O11D—C11D—C21D	122.8
C3B—C2B—C1B	121.46 (19)	O11D—C11D—C31D	119.32 (16)
C3B—C2B—H2B	119.3	C21D—C11D—C31D	117.85 (16)
C1B—C2B—H2B	119.3	H24D—C22D—H25D	109.5
C4B—C3B—C2B	119.8 (2)	H24D—C22D—H26D	109.5
C4B—C3B—H3B	120.1	H25D—C22D—H26D	109.5
C2B—C3B—H3B	120.1	H34D—C32D—H35D	109.5
O1B—C4B—C5B	117.14 (18)	H34D—C32D—H36D	109.5
O1B—C4B—C3B	123.20 (19)	H35D—C32D—H36D	109.5
C6A—C1A—C2A—C3A	−1.5 (3)	C6B—C1B—C2B—C3B	−0.9 (3)
C7A—C1A—C2A—C3A	179.76 (18)	C7B—C1B—C2B—C3B	179.19 (19)
C1A—C2A—C3A—C4A	0.6 (3)	C1B—C2B—C3B—C4B	0.3 (3)
C2A—C3A—C4A—C5A	0.6 (3)	C2B—C3B—C4B—O1B	−178.70 (19)
C2A—C3A—C4A—O1A	179.57 (17)	C2B—C3B—C4B—C5B	−0.1 (3)
O1A—C4A—C5A—C6A	−179.70 (17)	O1B—C4B—C5B—C6B	179.13 (18)
C3A—C4A—C5A—C6A	−0.8 (3)	C3B—C4B—C5B—C6B	0.4 (3)
C4A—C5A—C6A—C1A	−0.2 (3)	C4B—C5B—C6B—C1B	−1.0 (3)
C2A—C1A—C6A—C5A	1.3 (3)	C2B—C1B—C6B—C5B	1.2 (3)
C7A—C1A—C6A—C5A	−179.88 (17)	C7B—C1B—C6B—C5B	−178.83 (17)
C2A—C1A—C7A—C7'A	−61.9 (3)	C2B—C1B—C7B—C7'B	−64.6 (3)
C6A—C1A—C7A—C7'A	119.4 (2)	C6B—C1B—C7B—C7'B	115.4 (2)
C2A—C1A—C7A—C8A	121.17 (19)	C2B—C1B—C7B—C8B	118.2 (2)
C6A—C1A—C7A—C8A	−57.5 (2)	C6B—C1B—C7B—C8B	−61.8 (2)
C7'A—C7A—C8A—C9A	115.2 (2)	C7'B—C7B—C8B—C9B	114.0 (2)
C1A—C7A—C8A—C9A	−67.9 (2)	C1B—C7B—C8B—C9B	−68.8 (2)
C6'A—C1'A—C2'A—C3'A	−2.1 (3)	C6'B—C1'B—C2'B—C3'B	0.5 (3)
C7'A—C1'A—C2'A—C3'A	177.82 (18)	C7'B—C1'B—C2'B—C3'B	−176.32 (18)
C1'A—C2'A—C3'A—C4'A	0.2 (3)	C1'B—C2'B—C3'B—C4'B	0.0 (3)
C2'A—C3'A—C4'A—O1'A	−179.16 (17)	C2'B—C3'B—C4'B—O1'B	177.42 (18)
C2'A—C3'A—C4'A—C5'A	1.5 (3)	C2'B—C3'B—C4'B—C5'B	−0.9 (3)
O1'A—C4'A—C5'A—C6'A	179.38 (17)	O1'B—C4'B—C5'B—C6'B	−177.07 (17)
C3'A—C4'A—C5'A—C6'A	−1.3 (3)	C3'B—C4'B—C5'B—C6'B	1.3 (3)
C4'A—C5'A—C6'A—C1'A	−0.6 (3)	C4'B—C5'B—C6'B—C1'B	−0.8 (3)
C2'A—C1'A—C6'A—C5'A	2.2 (3)	C2'B—C1'B—C6'B—C5'B	0.0 (3)
C7'A—C1'A—C6'A—C5'A	−177.64 (17)	C7'B—C1'B—C6'B—C5'B	176.81 (17)
C1A—C7A—C7'A—C1'A	−178.92 (17)	C1B—C7B—C7'B—C1'B	−179.10 (17)
C8A—C7A—C7'A—C1'A	−2.3 (3)	C8B—C7B—C7'B—C1'B	−2.1 (3)
C1A—C7A—C7'A—C8'A	−1.3 (3)	C1B—C7B—C7'B—C8'B	0.1 (3)
C8A—C7A—C7'A—C8'A	175.33 (18)	C8B—C7B—C7'B—C8'B	177.06 (18)
C6'A—C1'A—C7'A—C7A	121.4 (2)	C2'B—C1'B—C7'B—C7B	−64.0 (3)
C2'A—C1'A—C7'A—C7A	−58.5 (3)	C6'B—C1'B—C7'B—C7B	119.3 (2)
C6'A—C1'A—C7'A—C8'A	−56.5 (2)	C2'B—C1'B—C7'B—C8'B	116.8 (2)
C2'A—C1'A—C7'A—C8'A	123.62 (19)	C6'B—C1'B—C7'B—C8'B	−59.9 (2)
C7A—C7'A—C8'A—C9'A	114.7 (2)	C7B—C7'B—C8'B—C9'B	120.3 (2)
C1'A—C7'A—C8'A—C9'A	−67.4 (2)	C1'B—C7'B—C8'B—C9'B	−60.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O11D^i	0.87 (3)	1.91 (3)	2.767 (3)	167 (3)
O1A—H1A···O12D^i	0.87 (3)	1.72 (3)	2.567 (9)	164 (3)
O1′A—H1′A···O1A^ii	0.93 (3)	1.84 (3)	2.763 (2)	170 (2)
O1B—H1B···O1′B^i	0.86 (3)	1.84 (3)	2.689 (2)	172 (3)
O1′B—H1′B···O1C	0.85 (3)	1.82 (3)	2.663 (2)	173 (3)

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

(d2-pr) diethylstilbestrol 2-propanol solvate (1/1)

Crystal data

C18H20O2·C3H8O	F(000) = 712
Mr = 328.43	Dx = 1.126 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.6981 (2) Å	Cell parameters from 5942 reflections
b = 21.1274 (7) Å	θ = 1.6–30.5°
c = 16.0891 (6) Å	µ = 0.07 mm^−1
β = 90.914 (2)°	T = 150 K
V = 1936.66 (12) Å^3	Needle, colourless
Z = 4	1.50 × 0.30 × 0.15 mm

Data collection

Siemens SMART CCD diffractometer	5850 independent reflections
Radiation source: fine-focus sealed tube	4661 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 8.3 pixels mm^-1	θmax = 30.5°, θmin = 1.6°
Sets of exposures each taken over 0.3° ω rotation scans	h = −8→7
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996)	k = −27→30
Tmin = 0.884, Tmax = 0.988	l = −22→22
24125 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0624P)^2 + 0.7023P] where P = (Fo^2 + 2Fc^2)/3
5850 reflections	(Δ/σ)max < 0.001
245 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.27 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1A	0.42858 (17)	−0.22714 (4)	−0.00649 (6)	0.0302 (2)
H1A	0.316 (3)	−0.2366 (8)	−0.0448 (12)	0.045*
O1'A	0.18876 (17)	0.19968 (4)	0.49071 (6)	0.0292 (2)
H1'A	0.315 (4)	0.2217 (9)	0.4899 (12)	0.044*
C1A	0.2684 (2)	−0.07243 (5)	0.14587 (7)	0.0224 (2)
C1'A	0.2106 (2)	0.04101 (5)	0.33456 (6)	0.0212 (2)
C2A	0.4801 (2)	−0.10577 (6)	0.15381 (7)	0.0264 (2)
H2A	0.596 (2)	−0.0925 (2)	0.1958 (7)	0.032*
C2'A	0.3918 (2)	0.08580 (5)	0.33431 (7)	0.0238 (2)
H2'A	0.524 (2)	0.07961 (12)	0.2973 (6)	0.029*
C3A	0.5299 (2)	−0.15741 (6)	0.10333 (7)	0.0261 (2)
H3A	0.674 (3)	−0.1792 (4)	0.10993 (14)	0.031*
C3'A	0.3884 (2)	0.13902 (5)	0.38555 (7)	0.0236 (2)
H3'A	0.514 (2)	0.1690 (5)	0.38420 (7)	0.028*
C4A	0.3677 (2)	−0.17695 (5)	0.04326 (7)	0.0230 (2)
C4'A	0.2012 (2)	0.14814 (5)	0.43863 (7)	0.0215 (2)
C5A	0.1554 (2)	−0.14476 (6)	0.03383 (8)	0.0277 (2)
H5A	0.041 (2)	−0.1584 (2)	−0.0075 (7)	0.033*
C5'A	0.0185 (2)	0.10431 (6)	0.44022 (7)	0.0254 (2)
H5'A	−0.114 (2)	0.11082 (12)	0.4772 (6)	0.031*
C6A	0.1087 (2)	−0.09272 (6)	0.08447 (7)	0.0270 (2)
H6A	−0.042 (3)	−0.0695 (4)	0.07671 (15)	0.032*
C6'A	0.0252 (2)	0.05124 (6)	0.38907 (7)	0.0249 (2)
H6'A	−0.101 (2)	0.0208 (5)	0.39121 (8)	0.030*
C7A	0.2224 (2)	−0.01525 (5)	0.19824 (7)	0.0229 (2)
C7'A	0.2249 (2)	−0.01743 (5)	0.28229 (7)	0.0216 (2)
C8A	0.1792 (3)	0.04513 (6)	0.14929 (8)	0.0312 (3)
H81A	0.1338 (6)	0.0796 (4)	0.1886 (5)	0.037*
H82A	0.0443 (17)	0.03823 (10)	0.1097 (5)	0.037*
C8'A	0.2429 (2)	−0.07842 (6)	0.33195 (7)	0.0266 (2)
H83A	0.2415 (2)	−0.1141 (4)	0.2935 (4)	0.032*
H84A	0.1050 (16)	−0.08214 (7)	0.3668 (4)	0.032*
C9A	0.3918 (3)	0.06671 (7)	0.10042 (10)	0.0461 (4)
H91A	0.3553 (10)	0.1062 (6)	0.0720 (8)	0.069*
H92A	0.4316 (16)	0.0345 (5)	0.0597 (8)	0.069*
H93A	0.5244 (18)	0.0731 (6)	0.1384 (5)	0.069*
C9'A	0.4629 (3)	−0.08253 (7)	0.38705 (9)	0.0363 (3)
H94A	0.4658 (11)	−0.1238 (5)	0.4163 (7)	0.055*
H95A	0.4617 (10)	−0.0478 (5)	0.4284 (6)	0.055*
H96A	0.6040 (16)	−0.0787 (6)	0.3522 (4)	0.055*
O1B	−0.11372 (16)	0.26658 (4)	0.11425 (5)	0.02721 (19)
H1B	−0.015 (3)	0.2814 (9)	0.0836 (12)	0.041*
C1B	0.1835 (3)	0.27142 (9)	0.22295 (12)	0.0536 (4)
H11B	0.298 (2)	0.2897 (6)	0.1812 (6)	0.080*
H12B	0.273 (2)	0.2450 (4)	0.2660 (9)	0.080*
H13B	0.0985 (12)	0.3075 (6)	0.2520 (8)	0.080*
C2B	0.0070 (2)	0.23026 (6)	0.17802 (8)	0.0291 (3)
H2B	0.0931 (15)	0.1935 (6)	0.1507 (5)	0.035*
C3B	−0.1761 (3)	0.20406 (11)	0.23445 (12)	0.0580 (5)
H31B	−0.292 (2)	0.1788 (7)	0.2011 (5)	0.087*
H32B	−0.258 (2)	0.2396 (5)	0.2626 (8)	0.087*
H33B	−0.0996 (11)	0.1763 (7)	0.2772 (8)	0.087*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0330 (5)	0.0271 (4)	0.0301 (4)	0.0082 (3)	−0.0074 (4)	−0.0087 (3)
O1'A	0.0311 (5)	0.0266 (4)	0.0301 (4)	−0.0036 (3)	0.0049 (4)	−0.0094 (3)
C1A	0.0274 (5)	0.0197 (5)	0.0200 (5)	−0.0007 (4)	0.0005 (4)	−0.0005 (4)
C1'A	0.0245 (5)	0.0196 (5)	0.0194 (5)	−0.0010 (4)	0.0003 (4)	0.0001 (4)
C2A	0.0281 (6)	0.0277 (6)	0.0233 (5)	0.0014 (4)	−0.0055 (4)	−0.0028 (4)
C2'A	0.0244 (5)	0.0235 (5)	0.0238 (5)	−0.0025 (4)	0.0055 (4)	−0.0017 (4)
C3A	0.0263 (6)	0.0268 (6)	0.0251 (5)	0.0055 (4)	−0.0034 (4)	−0.0013 (4)
C3'A	0.0237 (5)	0.0221 (5)	0.0251 (5)	−0.0044 (4)	0.0024 (4)	−0.0020 (4)
C4A	0.0277 (6)	0.0198 (5)	0.0215 (5)	0.0012 (4)	−0.0003 (4)	−0.0009 (4)
C4'A	0.0243 (5)	0.0209 (5)	0.0192 (5)	0.0002 (4)	−0.0010 (4)	−0.0011 (4)
C5A	0.0260 (6)	0.0278 (6)	0.0290 (6)	0.0030 (4)	−0.0064 (4)	−0.0065 (4)
C5'A	0.0242 (5)	0.0278 (6)	0.0244 (5)	−0.0019 (4)	0.0054 (4)	−0.0025 (4)
C6A	0.0259 (6)	0.0260 (5)	0.0290 (6)	0.0041 (4)	−0.0034 (4)	−0.0045 (4)
C6'A	0.0237 (5)	0.0249 (5)	0.0262 (5)	−0.0060 (4)	0.0033 (4)	−0.0012 (4)
C7A	0.0262 (5)	0.0197 (5)	0.0227 (5)	0.0002 (4)	0.0002 (4)	−0.0006 (4)
C7'A	0.0234 (5)	0.0186 (5)	0.0228 (5)	−0.0020 (4)	0.0005 (4)	−0.0001 (4)
C8A	0.0475 (8)	0.0227 (5)	0.0235 (5)	0.0048 (5)	0.0003 (5)	0.0016 (4)
C8'A	0.0349 (6)	0.0210 (5)	0.0239 (5)	−0.0027 (4)	0.0004 (4)	0.0019 (4)
C9A	0.0705 (11)	0.0324 (7)	0.0360 (7)	−0.0041 (7)	0.0155 (7)	0.0069 (6)
C9'A	0.0450 (8)	0.0327 (7)	0.0311 (6)	0.0048 (6)	−0.0075 (6)	0.0035 (5)
O1B	0.0311 (5)	0.0266 (4)	0.0238 (4)	−0.0014 (3)	−0.0017 (3)	0.0018 (3)
C1B	0.0542 (10)	0.0503 (10)	0.0554 (10)	−0.0083 (8)	−0.0272 (8)	0.0094 (8)
C2B	0.0341 (6)	0.0253 (6)	0.0277 (6)	0.0015 (5)	−0.0013 (5)	0.0025 (4)
C3B	0.0478 (9)	0.0772 (13)	0.0491 (9)	−0.0105 (9)	0.0037 (7)	0.0314 (9)

Geometric parameters (Å, º)

O1A—C4A	1.3763 (13)	C7A—C7'A	1.3530 (15)
O1A—H1A	0.90 (2)	C7A—C8A	1.5173 (16)
O1'A—C4'A	1.3765 (13)	C7'A—C8'A	1.5187 (15)
O1'A—H1'A	0.86 (2)	C8A—C9A	1.525 (2)
C1A—C6A	1.3996 (16)	C8A—H81A	1.0008
C1A—C2A	1.4008 (16)	C8A—H82A	1.0008
C1A—C7A	1.4982 (15)	C8'A—C9'A	1.5263 (19)
C1'A—C2'A	1.4002 (15)	C8'A—H83A	0.9758
C1'A—C6'A	1.4008 (15)	C8'A—H84A	0.9758
C1'A—C7'A	1.4968 (15)	C9A—H91A	0.9732
C2A—C3A	1.3921 (16)	C9A—H92A	0.9732
C2A—H2A	0.9767	C9A—H93A	0.9732
C2'A—C3'A	1.3945 (15)	C9'A—H94A	0.9905
C2'A—H2'A	0.9761	C9'A—H95A	0.9905
C3A—C4A	1.3894 (16)	C9'A—H96A	0.9905
C3A—H3A	0.9455	O1B—C2B	1.4466 (15)
C3'A—C4'A	1.3905 (15)	O1B—H1B	0.818 (19)
C3'A—H3'A	0.9544	C1B—C2B	1.506 (2)
C4A—C5A	1.3938 (16)	C1B—H11B	1.0208
C4'A—C5'A	1.3936 (16)	C1B—H12B	1.0208
C5A—C6A	1.3966 (16)	C1B—H13B	1.0208
C5A—H5A	0.9668	C2B—C3B	1.500 (2)
C5'A—C6'A	1.3917 (16)	C2B—H2B	1.0212
C5'A—H5'A	0.9775	C3B—H31B	0.9988
C6A—H6A	0.9927	C3B—H32B	0.9988
C6'A—H6'A	0.9664	C3B—H33B	0.9988
C4A—O1A—H1A	112.5 (12)	C7A—C8A—C9A	113.29 (12)
C4'A—O1'A—H1'A	111.7 (13)	C7A—C8A—H81A	108.9
C6A—C1A—C2A	117.35 (10)	C9A—C8A—H81A	108.9
C6A—C1A—C7A	121.76 (10)	C7A—C8A—H82A	108.9
C2A—C1A—C7A	120.81 (10)	C9A—C8A—H82A	108.9
C2'A—C1'A—C6'A	117.45 (10)	H81A—C8A—H82A	107.7
C2'A—C1'A—C7'A	120.62 (10)	C7'A—C8'A—C9'A	113.70 (10)
C6'A—C1'A—C7'A	121.81 (10)	C7'A—C8'A—H83A	108.8
C3A—C2A—C1A	121.61 (11)	C9'A—C8'A—H83A	108.8
C3A—C2A—H2A	119.2	C7'A—C8'A—H84A	108.8
C1A—C2A—H2A	119.2	C9'A—C8'A—H84A	108.8
C3'A—C2'A—C1'A	121.73 (10)	H83A—C8'A—H84A	107.7
C3'A—C2'A—H2'A	119.1	C8A—C9A—H91A	109.5
C1'A—C2'A—H2'A	119.1	C8A—C9A—H92A	109.5
C4A—C3A—C2A	119.95 (11)	H91A—C9A—H92A	109.5
C4A—C3A—H3A	120.0	C8A—C9A—H93A	109.5
C2A—C3A—H3A	120.0	H91A—C9A—H93A	109.5
C4'A—C3'A—C2'A	119.53 (10)	H92A—C9A—H93A	109.5
C4'A—C3'A—H3'A	120.2	C8'A—C9'A—H94A	109.5
C2'A—C3'A—H3'A	120.2	C8'A—C9'A—H95A	109.5
O1A—C4A—C3A	117.54 (10)	H94A—C9'A—H95A	109.5
O1A—C4A—C5A	122.62 (10)	C8'A—C9'A—H96A	109.5
C3A—C4A—C5A	119.82 (10)	H94A—C9'A—H96A	109.5
O1'A—C4'A—C3'A	122.07 (10)	H95A—C9'A—H96A	109.5
O1'A—C4'A—C5'A	117.96 (10)	C2B—O1B—H1B	107.8 (13)
C3'A—C4'A—C5'A	119.98 (10)	C2B—C1B—H11B	109.5
C4A—C5A—C6A	119.58 (11)	C2B—C1B—H12B	109.5
C4A—C5A—H5A	120.2	H11B—C1B—H12B	109.5
C6A—C5A—H5A	120.2	C2B—C1B—H13B	109.5
C6'A—C5'A—C4'A	119.80 (10)	H11B—C1B—H13B	109.5
C6'A—C5'A—H5'A	120.1	H12B—C1B—H13B	109.5
C4'A—C5'A—H5'A	120.1	O1B—C2B—C3B	107.31 (12)
C5A—C6A—C1A	121.69 (11)	O1B—C2B—C1B	109.91 (11)
C5A—C6A—H6A	119.2	C3B—C2B—C1B	112.85 (14)
C1A—C6A—H6A	119.2	O1B—C2B—H2B	108.9
C5'A—C6'A—C1'A	121.51 (10)	C3B—C2B—H2B	108.9
C5'A—C6'A—H6'A	119.2	C1B—C2B—H2B	108.9
C1'A—C6'A—H6'A	119.2	C2B—C3B—H31B	109.5
C7'A—C7A—C1A	122.38 (10)	C2B—C3B—H32B	109.5
C7'A—C7A—C8A	123.12 (10)	H31B—C3B—H32B	109.5
C1A—C7A—C8A	114.48 (9)	C2B—C3B—H33B	109.5
C7A—C7'A—C1'A	122.26 (10)	H31B—C3B—H33B	109.5
C7A—C7'A—C8'A	123.65 (10)	H32B—C3B—H33B	109.5
C1'A—C7'A—C8'A	114.09 (9)
C6A—C1A—C2A—C3A	−0.55 (18)	C2'A—C1'A—C6'A—C5'A	0.97 (17)
C7A—C1A—C2A—C3A	−177.31 (11)	C7'A—C1'A—C6'A—C5'A	177.06 (11)
C6'A—C1'A—C2'A—C3'A	−0.57 (17)	C6A—C1A—C7A—C7'A	124.78 (13)
C7'A—C1'A—C2'A—C3'A	−176.70 (11)	C2A—C1A—C7A—C7'A	−58.60 (16)
C1A—C2A—C3A—C4A	0.05 (18)	C6A—C1A—C7A—C8A	−56.68 (15)
C1'A—C2'A—C3'A—C4'A	0.15 (18)	C2A—C1A—C7A—C8A	119.94 (13)
C2A—C3A—C4A—O1A	178.22 (11)	C1A—C7A—C7'A—C1'A	171.70 (10)
C2A—C3A—C4A—C5A	−0.06 (18)	C8A—C7A—C7'A—C1'A	−6.72 (18)
C2'A—C3'A—C4'A—O1'A	179.84 (11)	C1A—C7A—C7'A—C8'A	−8.09 (18)
C2'A—C3'A—C4'A—C5'A	−0.11 (17)	C8A—C7A—C7'A—C8'A	173.49 (12)
O1A—C4A—C5A—C6A	−177.61 (11)	C2'A—C1'A—C7'A—C7A	−65.50 (16)
C3A—C4A—C5A—C6A	0.59 (18)	C6'A—C1'A—C7'A—C7A	118.53 (13)
O1'A—C4'A—C5'A—C6'A	−179.44 (11)	C2'A—C1'A—C7'A—C8'A	114.30 (12)
C3'A—C4'A—C5'A—C6'A	0.51 (18)	C6'A—C1'A—C7'A—C8'A	−61.66 (14)
C4A—C5A—C6A—C1A	−1.13 (19)	C7'A—C7A—C8A—C9A	114.08 (14)
C2A—C1A—C6A—C5A	1.09 (18)	C1A—C7A—C8A—C9A	−64.46 (15)
C7A—C1A—C6A—C5A	177.82 (11)	C7A—C7'A—C8'A—C9'A	117.77 (13)
C4'A—C5'A—C6'A—C1'A	−0.96 (18)	C1'A—C7'A—C8'A—C9'A	−62.03 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O1B^i	0.90 (2)	1.71 (2)	2.6115 (13)	171.0 (17)
O1′A—H1′A···O1A^ii	0.86 (2)	1.84 (2)	2.6817 (13)	170.1 (19)
O1B—H1B···O1′A^iii	0.818 (19)	1.95 (2)	2.7457 (13)	165.1 (18)

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

(dtbut) diethylstilbestrol tert-butanol solvate (1/4)

Crystal data

C18H20O2·4(C4H10O)	Z = 1
Mr = 564.84	F(000) = 372
Triclinic, P1	Dx = 1.003 Mg m^−3
a = 6.2717 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.4330 (8) Å	Cell parameters from 3903 reflections
c = 20.364 (2) Å	θ = 2.8–25.0°
α = 85.140 (2)°	µ = 0.07 mm^−1
β = 85.031 (2)°	T = 150 K
γ = 82.626 (2)°	Plate, colourless
V = 935.34 (17) Å^3	1.00 × 0.50 × 0.10 mm

Data collection

Siemens SMART CCD diffractometer	3281 independent reflections
Radiation source: fine-focus sealed tube	2514 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
Detector resolution: 8.3 pixels mm^-1	θmax = 25.0°, θmin = 2.9°
Sets of exposures each taken over 0.3° ω rotation scans	h = −7→7
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996)	k = −8→8
Tmin = 0.935, Tmax = 0.993	l = −24→22
7061 measured 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)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.165	w = 1/[σ^2(Fo^2) + (0.076P)^2 + 0.2702P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.006
3281 reflections	Δρmax = 0.17 e Å^−3
533 parameters	Δρmin = −0.15 e Å^−3
1428 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.032 (6)

Special details

Refinement. Refinement of F² against ALL reflections.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1A	0.1714 (2)	0.27709 (17)	0.25952 (6)	0.0646 (4)	0.451 (4)
H1A	0.040 (4)	0.301 (3)	0.2856 (12)	0.093 (8)*
C11A	0.0533 (8)	0.1214 (6)	0.0752 (2)	0.0550 (11)	0.451 (4)
C21A	−0.1057 (9)	0.1279 (7)	0.1261 (2)	0.0541 (11)	0.451 (4)
H21A	−0.2420	0.0933	0.1189	0.065*	0.451 (4)
C31A	−0.0743 (9)	0.1832 (8)	0.1875 (2)	0.0534 (11)	0.451 (4)
H31A	−0.1893	0.1908	0.2211	0.064*	0.451 (4)
C41A	0.1259 (10)	0.2272 (8)	0.1994 (2)	0.0513 (10)	0.451 (4)
C51A	0.2862 (10)	0.2228 (8)	0.1492 (2)	0.0532 (10)	0.451 (4)
H51A	0.4227	0.2567	0.1565	0.064*	0.451 (4)
C61A	0.2513 (9)	0.1696 (7)	0.0883 (2)	0.0546 (11)	0.451 (4)
H61A	0.3654	0.1658	0.0544	0.066*	0.451 (4)
C71A	0.0112 (9)	0.0740 (8)	0.0073 (2)	0.0580 (11)	0.451 (4)
C81A	−0.0225 (15)	0.2399 (11)	−0.0412 (4)	0.0689 (16)	0.451 (4)
H81A	0.0016	0.2020	−0.0870	0.083*	0.451 (4)
H82A	0.0832	0.3242	−0.0353	0.083*	0.451 (4)
C91A	−0.2624 (11)	0.3424 (7)	−0.0298 (2)	0.0896 (17)	0.451 (4)
H91A	−0.2896	0.4361	−0.0660	0.134*	0.451 (4)
H92A	−0.2777	0.3993	0.0123	0.134*	0.451 (4)
H93A	−0.3666	0.2543	−0.0288	0.134*	0.451 (4)
O12A	0.1714 (2)	0.27709 (17)	0.25952 (6)	0.0646 (4)	0.421 (4)
C12A	0.0703 (8)	0.0496 (6)	0.0871 (2)	0.0482 (9)	0.421 (4)
C22A	−0.0918 (9)	0.0676 (7)	0.1374 (2)	0.0545 (12)	0.421 (4)
H22A	−0.2264	0.0269	0.1322	0.065*	0.421 (4)
C32A	−0.0630 (9)	0.1432 (9)	0.1952 (3)	0.0537 (12)	0.421 (4)
H32A	−0.1759	0.1526	0.2295	0.064*	0.421 (4)
C42A	0.1317 (11)	0.2054 (8)	0.2027 (2)	0.0488 (10)	0.421 (4)
C52A	0.2960 (10)	0.1869 (9)	0.1537 (2)	0.0523 (12)	0.421 (4)
H52A	0.4308	0.2269	0.1593	0.063*	0.421 (4)
C62A	0.2655 (9)	0.1103 (9)	0.0965 (3)	0.0558 (11)	0.421 (4)
H62A	0.3799	0.0987	0.0627	0.067*	0.421 (4)
C72A	0.0417 (7)	−0.0446 (7)	0.0270 (2)	0.0547 (11)	0.421 (4)
C82A	0.1167 (13)	−0.2486 (11)	0.0331 (4)	0.0714 (19)	0.421 (4)
H83A	0.1287	−0.2957	−0.0113	0.086*	0.421 (4)
H84A	0.2617	−0.2694	0.0501	0.086*	0.421 (4)
C92A	−0.0254 (19)	−0.3451 (9)	0.0755 (4)	0.112 (3)	0.421 (4)
H94A	−0.1559	−0.2635	0.0875	0.169*	0.421 (4)
H95A	0.0450	−0.3929	0.1156	0.169*	0.421 (4)
H96A	−0.0644	−0.4463	0.0530	0.169*	0.421 (4)
O13A	0.1714 (2)	0.27709 (17)	0.25952 (6)	0.0646 (4)	0.128 (3)
C13A	0.0470 (19)	0.1724 (16)	0.0682 (4)	0.0538 (16)	0.128 (3)
C23A	−0.1094 (16)	0.2625 (15)	0.1096 (4)	0.0520 (16)	0.128 (3)
H23A	−0.2483	0.3007	0.0945	0.062*	0.128 (3)
C33A	−0.0688 (14)	0.2986 (14)	0.1725 (4)	0.0527 (15)	0.128 (3)
H33A	−0.1792	0.3625	0.1995	0.063*	0.128 (3)
C43A	0.1303 (15)	0.2429 (12)	0.1964 (3)	0.0522 (15)	0.128 (3)
C53A	0.2883 (16)	0.154 (2)	0.1561 (4)	0.0524 (16)	0.128 (3)
H53A	0.4272	0.1173	0.1713	0.063*	0.128 (3)
C63A	0.2458 (18)	0.118 (2)	0.0928 (5)	0.0532 (16)	0.128 (3)
H63A	0.3566	0.0550	0.0658	0.064*	0.128 (3)
C73A	−0.009 (3)	0.122 (2)	0.0023 (5)	0.0550 (19)	0.128 (3)
C83A	−0.043 (4)	0.286 (4)	−0.0475 (9)	0.064 (3)	0.128 (3)
H85A	−0.1286	0.3894	−0.0260	0.077*	0.128 (3)
H86A	−0.1217	0.2559	−0.0843	0.077*	0.128 (3)
C93A	0.192 (4)	0.341 (2)	−0.0753 (10)	0.083 (4)	0.128 (3)
H97A	0.1753	0.4647	−0.0966	0.125*	0.128 (3)
H98A	0.2576	0.2557	−0.1076	0.125*	0.128 (3)
H99A	0.2839	0.3356	−0.0386	0.125*	0.128 (3)
O11B	0.4748 (13)	0.4907 (9)	0.2940 (4)	0.0676 (14)	0.515 (5)
H1B	0.382 (4)	0.431 (3)	0.2829 (12)	0.091 (8)*
C11B	0.4011 (8)	0.6780 (8)	0.2738 (3)	0.0649 (12)	0.515 (5)
C21B	0.5894 (10)	0.7826 (12)	0.2795 (4)	0.105 (2)	0.515 (5)
H21B	0.7094	0.7400	0.2483	0.157*	0.515 (5)
H22B	0.6351	0.7630	0.3246	0.157*	0.515 (5)
H23B	0.5457	0.9126	0.2692	0.157*	0.515 (5)
C31B	0.2113 (10)	0.7428 (8)	0.3205 (3)	0.0887 (15)	0.515 (5)
H31B	0.2568	0.7353	0.3655	0.133*	0.515 (5)
H32B	0.0963	0.6658	0.3190	0.133*	0.515 (5)
H33B	0.1577	0.8691	0.3071	0.133*	0.515 (5)
C41B	0.3357 (12)	0.6904 (7)	0.2045 (2)	0.0909 (15)	0.515 (5)
H41B	0.4598	0.6472	0.1749	0.136*	0.515 (5)
H42B	0.2847	0.8172	0.1910	0.136*	0.515 (5)
H43B	0.2197	0.6150	0.2023	0.136*	0.515 (5)
O12B	0.457 (2)	0.5005 (15)	0.3003 (7)	0.078 (3)	0.318 (5)
C12B	0.4327 (14)	0.6744 (14)	0.2622 (5)	0.0761 (19)	0.318 (5)
C22B	0.5142 (17)	0.8080 (19)	0.3030 (6)	0.089 (3)	0.318 (5)
H24B	0.6679	0.7722	0.3086	0.134*	0.318 (5)
H25B	0.4337	0.8082	0.3465	0.134*	0.318 (5)
H26B	0.4938	0.9301	0.2805	0.134*	0.318 (5)
C32B	0.1980 (11)	0.7246 (10)	0.2507 (6)	0.089 (2)	0.318 (5)
H34B	0.1138	0.7369	0.2933	0.133*	0.318 (5)
H35B	0.1480	0.6293	0.2276	0.133*	0.318 (5)
H36B	0.1793	0.8403	0.2238	0.133*	0.318 (5)
C42B	0.5655 (18)	0.6575 (15)	0.1971 (5)	0.109 (3)	0.318 (5)
H44B	0.7182	0.6273	0.2052	0.163*	0.318 (5)
H45B	0.5454	0.7731	0.1702	0.163*	0.318 (5)
H46B	0.5192	0.5611	0.1737	0.163*	0.318 (5)
O13B	0.417 (3)	0.4912 (19)	0.3145 (10)	0.072 (3)	0.166 (4)
C13B	0.390 (2)	0.6790 (19)	0.2874 (8)	0.075 (2)	0.166 (4)
C23B	0.525 (3)	0.779 (3)	0.3267 (11)	0.092 (4)	0.166 (4)
H27B	0.6782	0.7362	0.3168	0.138*	0.166 (4)
H28B	0.4865	0.7549	0.3740	0.138*	0.166 (4)
H29B	0.4985	0.9097	0.3146	0.138*	0.166 (4)
C33B	0.153 (2)	0.748 (3)	0.2977 (14)	0.086 (4)	0.166 (4)
H37B	0.1092	0.7439	0.3451	0.129*	0.166 (4)
H38B	0.0683	0.6720	0.2759	0.129*	0.166 (4)
H39B	0.1277	0.8742	0.2787	0.129*	0.166 (4)
C43B	0.460 (4)	0.689 (3)	0.2153 (8)	0.097 (3)	0.166 (4)
H47B	0.6132	0.6418	0.2091	0.145*	0.166 (4)
H48B	0.4381	0.8155	0.1971	0.145*	0.166 (4)
H49B	0.3750	0.6153	0.1925	0.145*	0.166 (4)
O11C	0.837 (2)	0.3217 (11)	0.3430 (3)	0.0733 (17)	0.515 (5)
H1C	0.723 (5)	0.383 (4)	0.3326 (12)	0.099 (9)*
C11C	0.8271 (10)	0.2898 (8)	0.4131 (3)	0.0670 (12)	0.515 (5)
C21C	1.0552 (9)	0.2147 (14)	0.4289 (7)	0.091 (2)	0.515 (5)
H21C	1.1548	0.3010	0.4108	0.137*	0.515 (5)
H22C	1.0960	0.0982	0.4092	0.137*	0.515 (5)
H23C	1.0619	0.1963	0.4770	0.137*	0.515 (5)
C31C	0.7588 (12)	0.4707 (9)	0.4433 (4)	0.0869 (17)	0.515 (5)
H31C	0.6112	0.5166	0.4329	0.130*	0.515 (5)
H32C	0.8564	0.5587	0.4252	0.130*	0.515 (5)
H33C	0.7650	0.4534	0.4914	0.130*	0.515 (5)
C41C	0.6687 (11)	0.1543 (9)	0.4357 (3)	0.0986 (19)	0.515 (5)
H41C	0.5247	0.2041	0.4228	0.148*	0.515 (5)
H42C	0.6646	0.1315	0.4839	0.148*	0.515 (5)
H43C	0.7148	0.0400	0.4150	0.148*	0.515 (5)
O12C	0.855 (3)	0.3697 (16)	0.3404 (5)	0.0609 (18)	0.318 (5)
C12C	0.8348 (16)	0.2783 (13)	0.4049 (5)	0.0725 (18)	0.318 (5)
C22C	1.0642 (14)	0.239 (2)	0.4254 (11)	0.083 (3)	0.318 (5)
H24C	1.1288	0.3526	0.4232	0.124*	0.318 (5)
H25C	1.1491	0.1555	0.3956	0.124*	0.318 (5)
H26C	1.0629	0.1827	0.4708	0.124*	0.318 (5)
C32C	0.697 (2)	0.4042 (16)	0.4506 (6)	0.096 (3)	0.318 (5)
H34C	0.5488	0.4242	0.4370	0.144*	0.318 (5)
H35C	0.7552	0.5208	0.4482	0.144*	0.318 (5)
H36C	0.6965	0.3490	0.4960	0.144*	0.318 (5)
C42C	0.7346 (10)	0.1036 (8)	0.4007 (3)	0.090 (2)	0.318 (5)
H44C	0.5839	0.1339	0.3905	0.135*	0.318 (5)
H45C	0.7412	0.0311	0.4431	0.135*	0.318 (5)
H46C	0.8145	0.0335	0.3658	0.135*	0.318 (5)
O13C	0.7727 (10)	0.2768 (8)	0.3456 (3)	0.066 (3)	0.166 (4)
C13C	0.8074 (10)	0.2286 (8)	0.4136 (3)	0.072 (2)	0.166 (4)
C23C	0.9896 (10)	0.0729 (8)	0.4134 (3)	0.092 (3)	0.166 (4)
H27C	1.1283	0.1220	0.4093	0.138*	0.166 (4)
H28C	0.9811	0.0002	0.3759	0.138*	0.166 (4)
H29C	0.9769	−0.0040	0.4547	0.138*	0.166 (4)
C33C	0.870 (2)	0.3910 (15)	0.4439 (6)	0.090 (3)	0.166 (4)
H37C	0.7441	0.4826	0.4490	0.135*	0.166 (4)
H38C	0.9835	0.4433	0.4150	0.135*	0.166 (4)
H39C	0.9240	0.3525	0.4873	0.135*	0.166 (4)
C43C	0.6003 (17)	0.169 (2)	0.4494 (7)	0.096 (4)	0.166 (4)
H47C	0.4822	0.2683	0.4447	0.143*	0.166 (4)
H48C	0.6218	0.1395	0.4963	0.143*	0.166 (4)
H49C	0.5642	0.0617	0.4300	0.143*	0.166 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0825 (10)	0.0666 (8)	0.0522 (7)	−0.0247 (7)	−0.0147 (6)	−0.0151 (6)
C11A	0.0698 (18)	0.051 (3)	0.0489 (15)	−0.021 (2)	−0.0063 (13)	−0.0101 (17)
C21A	0.0623 (18)	0.054 (3)	0.0495 (17)	−0.013 (2)	−0.0102 (13)	−0.0094 (19)
C31A	0.0637 (17)	0.051 (3)	0.0472 (17)	−0.0060 (18)	−0.0088 (14)	−0.0095 (18)
C41A	0.0718 (19)	0.039 (2)	0.0470 (16)	−0.0115 (19)	−0.0142 (14)	−0.0080 (18)
C51A	0.0702 (19)	0.044 (3)	0.0502 (15)	−0.0260 (19)	−0.0118 (13)	0.0034 (17)
C61A	0.0697 (18)	0.051 (3)	0.0471 (16)	−0.0248 (19)	−0.0044 (14)	0.0015 (18)
C71A	0.068 (2)	0.061 (3)	0.0489 (17)	−0.0204 (19)	−0.0058 (15)	−0.0061 (18)
C81A	0.098 (3)	0.064 (4)	0.053 (2)	−0.037 (3)	−0.012 (3)	−0.001 (2)
C91A	0.140 (4)	0.053 (3)	0.070 (3)	0.011 (3)	−0.013 (3)	0.000 (2)
O12A	0.0825 (10)	0.0666 (8)	0.0522 (7)	−0.0247 (7)	−0.0147 (6)	−0.0151 (6)
C12A	0.0635 (17)	0.040 (2)	0.0409 (17)	0.0026 (18)	−0.0161 (13)	−0.0051 (15)
C22A	0.0534 (18)	0.059 (3)	0.055 (2)	−0.004 (2)	−0.0143 (14)	−0.017 (2)
C32A	0.0587 (19)	0.057 (3)	0.0490 (19)	−0.0134 (19)	−0.0044 (15)	−0.0138 (19)
C42A	0.0656 (19)	0.041 (2)	0.0437 (17)	−0.0137 (19)	−0.0126 (14)	−0.0045 (17)
C52A	0.0672 (19)	0.041 (3)	0.0538 (17)	−0.0284 (19)	−0.0029 (14)	0.0007 (18)
C62A	0.0728 (19)	0.044 (3)	0.0524 (19)	−0.019 (2)	0.0041 (16)	−0.0062 (19)
C72A	0.071 (2)	0.047 (2)	0.046 (2)	0.0122 (17)	−0.0226 (16)	−0.0111 (18)
C82A	0.103 (5)	0.050 (3)	0.062 (4)	0.019 (3)	−0.037 (4)	−0.019 (2)
C92A	0.197 (8)	0.067 (3)	0.081 (4)	−0.034 (4)	−0.039 (5)	0.004 (3)
O13A	0.0825 (10)	0.0666 (8)	0.0522 (7)	−0.0247 (7)	−0.0147 (6)	−0.0151 (6)
C13A	0.068 (3)	0.047 (3)	0.050 (2)	−0.017 (3)	−0.005 (2)	−0.009 (3)
C23A	0.062 (3)	0.050 (4)	0.048 (3)	−0.014 (3)	−0.010 (2)	−0.009 (3)
C33A	0.065 (3)	0.048 (4)	0.048 (3)	−0.016 (3)	−0.007 (2)	−0.009 (3)
C43A	0.069 (3)	0.044 (3)	0.049 (2)	−0.017 (3)	−0.0127 (19)	−0.010 (3)
C53A	0.065 (3)	0.042 (4)	0.052 (2)	−0.018 (3)	−0.005 (2)	−0.002 (3)
C63A	0.068 (3)	0.045 (4)	0.047 (3)	−0.011 (3)	−0.001 (2)	−0.001 (3)
C73A	0.076 (4)	0.045 (4)	0.049 (3)	−0.021 (4)	−0.004 (3)	−0.008 (3)
C83A	0.098 (6)	0.050 (6)	0.051 (4)	−0.033 (6)	−0.007 (5)	−0.002 (4)
C93A	0.112 (8)	0.063 (8)	0.080 (9)	−0.042 (8)	0.013 (8)	−0.004 (6)
O11B	0.062 (3)	0.0496 (18)	0.098 (3)	−0.0047 (17)	−0.044 (2)	−0.0085 (19)
C11B	0.064 (2)	0.0444 (18)	0.093 (3)	−0.0143 (17)	−0.0312 (19)	−0.005 (2)
C21B	0.097 (3)	0.088 (4)	0.142 (5)	−0.052 (4)	−0.035 (3)	0.007 (4)
C31B	0.088 (3)	0.059 (2)	0.115 (3)	0.005 (2)	−0.012 (2)	0.001 (3)
C41B	0.123 (4)	0.061 (2)	0.093 (2)	−0.012 (3)	−0.044 (3)	0.007 (2)
O12B	0.081 (6)	0.049 (3)	0.110 (6)	−0.006 (4)	−0.047 (5)	−0.003 (4)
C12B	0.069 (3)	0.057 (3)	0.105 (4)	−0.010 (3)	−0.030 (3)	0.005 (3)
C22B	0.090 (5)	0.052 (4)	0.131 (7)	−0.014 (4)	−0.039 (5)	0.003 (5)
C32B	0.071 (3)	0.056 (3)	0.139 (6)	−0.008 (3)	−0.036 (4)	0.018 (4)
C42B	0.110 (5)	0.085 (5)	0.126 (5)	0.001 (5)	−0.001 (4)	0.000 (4)
O13B	0.071 (7)	0.040 (3)	0.111 (7)	−0.008 (4)	−0.045 (6)	0.002 (4)
C13B	0.072 (4)	0.047 (3)	0.110 (5)	−0.010 (4)	−0.033 (4)	0.011 (4)
C23B	0.096 (7)	0.046 (6)	0.140 (8)	−0.022 (6)	−0.037 (7)	0.000 (7)
C33B	0.077 (4)	0.053 (6)	0.124 (9)	0.002 (4)	−0.030 (6)	0.021 (8)
C43B	0.103 (8)	0.069 (7)	0.115 (5)	−0.007 (8)	−0.019 (6)	0.010 (5)
O11C	0.064 (4)	0.100 (4)	0.0503 (19)	0.028 (3)	−0.0176 (18)	−0.018 (2)
C11C	0.059 (2)	0.092 (2)	0.050 (2)	0.0027 (17)	−0.020 (2)	−0.0120 (19)
C21C	0.070 (2)	0.124 (5)	0.077 (4)	0.011 (2)	−0.033 (3)	0.001 (4)
C31C	0.091 (5)	0.110 (3)	0.062 (3)	0.004 (3)	−0.017 (3)	−0.032 (3)
C41C	0.085 (3)	0.114 (3)	0.099 (4)	−0.017 (3)	−0.025 (3)	0.005 (3)
O12C	0.052 (4)	0.074 (4)	0.058 (3)	0.005 (3)	−0.018 (2)	−0.015 (2)
C12C	0.066 (3)	0.098 (3)	0.056 (3)	−0.007 (3)	−0.020 (3)	−0.011 (3)
C22C	0.078 (3)	0.109 (6)	0.064 (5)	−0.004 (3)	−0.035 (4)	−0.008 (5)
C32C	0.086 (5)	0.137 (6)	0.065 (4)	−0.009 (5)	−0.002 (4)	−0.026 (5)
C42C	0.079 (4)	0.101 (4)	0.092 (5)	−0.018 (3)	−0.021 (4)	0.005 (3)
O13C	0.062 (6)	0.088 (6)	0.047 (3)	−0.001 (4)	−0.010 (3)	−0.002 (3)
C13C	0.063 (4)	0.102 (4)	0.048 (3)	−0.004 (3)	−0.013 (3)	0.000 (4)
C23C	0.082 (6)	0.106 (6)	0.082 (7)	0.007 (5)	−0.017 (5)	0.021 (5)
C33C	0.082 (6)	0.128 (5)	0.064 (5)	−0.012 (5)	−0.017 (5)	−0.022 (5)
C43C	0.093 (6)	0.115 (8)	0.074 (7)	−0.017 (5)	0.018 (6)	0.001 (7)

Geometric parameters (Å, º)

O1A—C41A	1.373 (4)	C41B—H43B	0.9800
O1A—H1A	0.95 (3)	O12B—C12B	1.448 (7)
C11A—C21A	1.373 (5)	O12B—H1B	0.85 (3)
C11A—C61A	1.389 (5)	C12B—C32B	1.505 (8)
C11A—C71A	1.509 (4)	C12B—C42B	1.508 (8)
C21A—C31A	1.387 (5)	C12B—C22B	1.510 (7)
C21A—H21A	0.9500	C22B—H24B	0.9800
C31A—C41A	1.383 (5)	C22B—H25B	0.9800
C31A—H31A	0.9500	C22B—H26B	0.9800
C41A—C51A	1.369 (5)	C32B—H34B	0.9800
C51A—C61A	1.377 (5)	C32B—H35B	0.9800
C51A—H51A	0.9500	C32B—H36B	0.9800
C61A—H61A	0.9500	C42B—H44B	0.9800
C71A—C71A^i	1.192 (11)	C42B—H45B	0.9800
C71A—C81A	1.518 (9)	C42B—H46B	0.9800
C81A—C91A	1.604 (12)	O13B—C13B	1.452 (7)
C81A—H81A	0.9900	O13B—H1B	0.87 (3)
C81A—H82A	0.9900	C13B—C43B	1.493 (9)
C91A—H91A	0.9800	C13B—C33B	1.512 (8)
C91A—H92A	0.9800	C13B—C23B	1.513 (8)
C91A—H93A	0.9800	C23B—H27B	0.9800
C12A—C22A	1.382 (5)	C23B—H28B	0.9800
C12A—C62A	1.391 (5)	C23B—H29B	0.9800
C12A—C72A	1.495 (4)	C33B—H37B	0.9800
C22A—C32A	1.381 (5)	C33B—H38B	0.9800
C22A—H22A	0.9500	C33B—H39B	0.9800
C32A—C42A	1.385 (5)	C43B—H47B	0.9800
C32A—H32A	0.9500	C43B—H48B	0.9800
C42A—C52A	1.373 (5)	C43B—H49B	0.9800
C52A—C62A	1.378 (5)	O11C—C11C	1.424 (5)
C52A—H52A	0.9500	O11C—H1C	0.83 (3)
C62A—H62A	0.9500	C11C—C21C	1.519 (5)
C72A—C72A^i	1.346 (9)	C11C—C41C	1.521 (6)
C72A—C82A	1.527 (9)	C11C—C31C	1.522 (6)
C82A—C92A	1.408 (13)	C21C—H21C	0.9800
C82A—H83A	0.9900	C21C—H22C	0.9800
C82A—H84A	0.9900	C21C—H23C	0.9800
C92A—H94A	0.9800	C31C—H31C	0.9800
C92A—H95A	0.9800	C31C—H32C	0.9800
C92A—H96A	0.9800	C31C—H33C	0.9800
C13A—C23A	1.380 (7)	C41C—H41C	0.9800
C13A—C63A	1.383 (7)	C41C—H42C	0.9800
C13A—C73A	1.506 (7)	C41C—H43C	0.9800
C23A—C33A	1.380 (7)	O12C—C12C	1.431 (6)
C23A—H23A	0.9500	O12C—H1C	0.85 (3)
C33A—C43A	1.381 (7)	C12C—C32C	1.513 (7)
C33A—H33A	0.9500	C12C—C22C	1.518 (7)
C43A—C53A	1.367 (7)	C12C—C42C	1.525 (7)
C53A—C63A	1.393 (7)	C22C—H24C	0.9800
C53A—H53A	0.9500	C22C—H25C	0.9800
C63A—H63A	0.9500	C22C—H26C	0.9800
C73A—C83A	1.524 (13)	C32C—H34C	0.9800
C73A—C73A^i	1.81 (3)	C32C—H35C	0.9800
C83A—C93A	1.618 (16)	C32C—H36C	0.9800
C83A—H85A	0.9900	C42C—H44C	0.9800
C83A—H86A	0.9900	C42C—H45C	0.9800
C93A—H97A	0.9800	C42C—H46C	0.9800
C93A—H98A	0.9800	O13C—C13C	1.427 (8)
C93A—H99A	0.9800	O13C—H1C	0.84 (3)
O11B—C11B	1.446 (5)	C13C—C33C	1.512 (7)
O11B—H1B	0.83 (3)	C13C—C23C	1.5182
C11B—C41B	1.495 (6)	C13C—C43C	1.530 (6)
C11B—C31B	1.512 (6)	C23C—H27C	0.9800
C11B—C21B	1.512 (5)	C23C—H28C	0.9800
C21B—H21B	0.9800	C23C—H29C	0.9800
C21B—H22B	0.9800	C33C—H37C	0.9800
C21B—H23B	0.9800	C33C—H38C	0.9800
C31B—H31B	0.9800	C33C—H39C	0.9800
C31B—H32B	0.9800	C43C—H47C	0.9800
C31B—H33B	0.9800	C43C—H48C	0.9800
C41B—H41B	0.9800	C43C—H49C	0.9800
C41B—H42B	0.9800
C41A—O1A—H1A	108.3 (15)	O12B—C12B—C42B	108.8 (6)
C21A—C11A—C61A	116.9 (3)	C32B—C12B—C42B	110.3 (6)
C21A—C11A—C71A	121.5 (4)	O12B—C12B—C22B	106.1 (6)
C61A—C11A—C71A	121.5 (4)	C32B—C12B—C22B	111.9 (6)
C11A—C21A—C31A	122.3 (4)	C42B—C12B—C22B	111.2 (6)
C11A—C21A—H21A	118.8	C12B—C22B—H24B	109.5
C31A—C21A—H21A	118.8	C12B—C22B—H25B	109.5
C41A—C31A—C21A	119.4 (4)	H24B—C22B—H25B	109.5
C41A—C31A—H31A	120.3	C12B—C22B—H26B	109.5
C21A—C31A—H31A	120.3	H24B—C22B—H26B	109.5
C51A—C41A—O1A	118.0 (4)	H25B—C22B—H26B	109.5
C51A—C41A—C31A	119.1 (3)	C12B—C32B—H34B	109.5
O1A—C41A—C31A	122.8 (4)	C12B—C32B—H35B	109.5
C41A—C51A—C61A	120.6 (4)	H34B—C32B—H35B	109.5
C41A—C51A—H51A	119.7	C12B—C32B—H36B	109.5
C61A—C51A—H51A	119.7	H34B—C32B—H36B	109.5
C51A—C61A—C11A	121.6 (4)	H35B—C32B—H36B	109.5
C51A—C61A—H61A	119.2	C12B—C42B—H44B	109.5
C11A—C61A—H61A	119.2	C12B—C42B—H45B	109.5
C71A^i—C71A—C11A	125.3 (6)	H44B—C42B—H45B	109.5
C71A^i—C71A—C81A	121.6 (6)	C12B—C42B—H46B	109.5
C11A—C71A—C81A	112.8 (4)	H44B—C42B—H46B	109.5
C71A—C81A—C91A	110.6 (6)	H45B—C42B—H46B	109.5
C71A—C81A—H81A	109.5	C13B—O13B—H1B	103 (2)
C91A—C81A—H81A	109.5	O13B—C13B—C43B	109.9 (7)
C71A—C81A—H82A	109.5	O13B—C13B—C33B	107.2 (7)
C91A—C81A—H82A	109.5	C43B—C13B—C33B	110.1 (7)
H81A—C81A—H82A	108.1	O13B—C13B—C23B	105.6 (6)
C81A—C91A—H91A	109.5	C43B—C13B—C23B	112.4 (7)
C81A—C91A—H92A	109.5	C33B—C13B—C23B	111.4 (7)
H91A—C91A—H92A	109.5	C13B—C23B—H27B	109.5
C81A—C91A—H93A	109.5	C13B—C23B—H28B	109.5
H91A—C91A—H93A	109.5	H27B—C23B—H28B	109.5
H92A—C91A—H93A	109.5	C13B—C23B—H29B	109.5
C22A—C12A—C62A	117.7 (3)	H27B—C23B—H29B	109.5
C22A—C12A—C72A	120.8 (4)	H28B—C23B—H29B	109.5
C62A—C12A—C72A	121.3 (4)	C13B—C33B—H37B	109.5
C32A—C22A—C12A	121.7 (4)	C13B—C33B—H38B	109.5
C32A—C22A—H22A	119.2	H37B—C33B—H38B	109.5
C12A—C22A—H22A	119.2	C13B—C33B—H39B	109.5
C22A—C32A—C42A	119.4 (4)	H37B—C33B—H39B	109.5
C22A—C32A—H32A	120.3	H38B—C33B—H39B	109.5
C42A—C32A—H32A	120.3	C13B—C43B—H47B	109.5
C52A—C42A—C32A	119.9 (4)	C13B—C43B—H48B	109.5
C42A—C52A—C62A	120.0 (4)	H47B—C43B—H48B	109.5
C42A—C52A—H52A	120.0	C13B—C43B—H49B	109.5
C62A—C52A—H52A	120.0	H47B—C43B—H49B	109.5
C52A—C62A—C12A	121.2 (4)	H48B—C43B—H49B	109.5
C52A—C62A—H62A	119.4	C11C—O11C—H1C	108.8 (19)
C12A—C62A—H62A	119.4	O11C—C11C—C21C	105.2 (4)
C72A^i—C72A—C12A	122.4 (5)	O11C—C11C—C41C	109.9 (4)
C72A^i—C72A—C82A	123.9 (5)	C21C—C11C—C41C	111.4 (4)
C12A—C72A—C82A	113.7 (4)	O11C—C11C—C31C	108.3 (4)
C92A—C82A—C72A	112.2 (6)	C21C—C11C—C31C	110.7 (4)
C92A—C82A—H83A	109.2	C41C—C11C—C31C	111.1 (4)
C72A—C82A—H83A	109.2	C11C—C21C—H21C	109.5
C92A—C82A—H84A	109.2	C11C—C21C—H22C	109.5
C72A—C82A—H84A	109.2	H21C—C21C—H22C	109.5
H83A—C82A—H84A	107.9	C11C—C21C—H23C	109.5
C82A—C92A—H94A	109.5	H21C—C21C—H23C	109.5
C82A—C92A—H95A	109.5	H22C—C21C—H23C	109.5
H94A—C92A—H95A	109.5	C11C—C31C—H31C	109.5
C82A—C92A—H96A	109.5	C11C—C31C—H32C	109.5
H94A—C92A—H96A	109.5	H31C—C31C—H32C	109.5
H95A—C92A—H96A	109.5	C11C—C31C—H33C	109.5
C23A—C13A—C63A	116.9 (5)	H31C—C31C—H33C	109.5
C23A—C13A—C73A	119.8 (6)	H32C—C31C—H33C	109.5
C63A—C13A—C73A	123.1 (6)	C11C—C41C—H41C	109.5
C33A—C23A—C13A	121.6 (6)	C11C—C41C—H42C	109.5
C33A—C23A—H23A	119.2	H41C—C41C—H42C	109.5
C13A—C23A—H23A	119.2	C11C—C41C—H43C	109.5
C23A—C33A—C43A	120.7 (6)	H41C—C41C—H43C	109.5
C23A—C33A—H33A	119.6	H42C—C41C—H43C	109.5
C43A—C33A—H33A	119.6	C12C—O12C—H1C	98 (2)
C53A—C43A—C33A	118.7 (5)	O12C—C12C—C32C	108.9 (6)
C43A—C53A—C63A	120.1 (6)	O12C—C12C—C22C	104.5 (5)
C43A—C53A—H53A	119.9	C32C—C12C—C22C	111.3 (6)
C63A—C53A—H53A	119.9	O12C—C12C—C42C	109.1 (6)
C13A—C63A—C53A	121.9 (6)	C32C—C12C—C42C	111.2 (6)
C13A—C63A—H63A	119.1	C22C—C12C—C42C	111.6 (6)
C53A—C63A—H63A	119.1	C12C—C22C—H24C	109.5
C13A—C73A—C83A	112.6 (9)	C12C—C22C—H25C	109.5
C13A—C73A—C73A^i	112.4 (11)	H24C—C22C—H25C	109.5
C83A—C73A—C73A^i	134.5 (12)	C12C—C22C—H26C	109.5
C73A—C83A—C93A	108.2 (11)	H24C—C22C—H26C	109.5
C73A—C83A—H85A	110.1	H25C—C22C—H26C	109.5
C93A—C83A—H85A	110.1	C12C—C32C—H34C	109.5
C73A—C83A—H86A	110.1	C12C—C32C—H35C	109.5
C93A—C83A—H86A	110.1	H34C—C32C—H35C	109.5
H85A—C83A—H86A	108.4	C12C—C32C—H36C	109.5
C83A—C93A—H97A	109.5	H34C—C32C—H36C	109.5
C83A—C93A—H98A	109.5	H35C—C32C—H36C	109.5
H97A—C93A—H98A	109.5	C12C—C42C—H44C	109.5
C83A—C93A—H99A	109.5	C12C—C42C—H45C	109.5
H97A—C93A—H99A	109.5	H44C—C42C—H45C	109.5
H98A—C93A—H99A	109.5	C12C—C42C—H46C	109.5
C11B—O11B—H1B	105.2 (17)	H44C—C42C—H46C	109.5
O11B—C11B—C41B	109.4 (4)	H45C—C42C—H46C	109.5
O11B—C11B—C31B	108.4 (4)	C13C—O13C—H1C	121.4 (18)
C41B—C11B—C31B	110.3 (4)	O13C—C13C—C33C	109.1 (5)
O11B—C11B—C21B	105.8 (4)	O13C—C13C—C23C	105.3
C41B—C11B—C21B	111.9 (5)	C33C—C13C—C23C	111.2 (5)
C31B—C11B—C21B	110.9 (4)	O13C—C13C—C43C	109.1 (5)
C11B—C21B—H21B	109.5	C33C—C13C—C43C	110.5 (6)
C11B—C21B—H22B	109.5	C23C—C13C—C43C	111.4 (5)
H21B—C21B—H22B	109.5	C13C—C23C—H27C	109.5
C11B—C21B—H23B	109.5	C13C—C23C—H28C	109.5
H21B—C21B—H23B	109.5	H27C—C23C—H28C	109.5
H22B—C21B—H23B	109.5	C13C—C23C—H29C	109.5
C11B—C31B—H31B	109.5	H27C—C23C—H29C	109.5
C11B—C31B—H32B	109.5	H28C—C23C—H29C	109.5
H31B—C31B—H32B	109.5	C13C—C33C—H37C	109.5
C11B—C31B—H33B	109.5	C13C—C33C—H38C	109.5
H31B—C31B—H33B	109.5	H37C—C33C—H38C	109.5
H32B—C31B—H33B	109.5	C13C—C33C—H39C	109.5
C11B—C41B—H41B	109.5	H37C—C33C—H39C	109.5
C11B—C41B—H42B	109.5	H38C—C33C—H39C	109.5
H41B—C41B—H42B	109.5	C13C—C43C—H47C	109.5
C11B—C41B—H43B	109.5	C13C—C43C—H48C	109.5
H41B—C41B—H43B	109.5	H47C—C43C—H48C	109.5
H42B—C41B—H43B	109.5	C13C—C43C—H49C	109.5
C12B—O12B—H1B	106.7 (19)	H47C—C43C—H49C	109.5
O12B—C12B—C32B	108.3 (6)	H48C—C43C—H49C	109.5
C61A—C11A—C21A—C31A	1.3 (4)	C22A—C12A—C62A—C52A	−0.4 (6)
C71A—C11A—C21A—C31A	−175.5 (4)	C72A—C12A—C62A—C52A	−175.9 (5)
C11A—C21A—C31A—C41A	−2.5 (6)	C22A—C12A—C72A—C72A^i	89.9 (7)
C21A—C31A—C41A—C51A	2.8 (8)	C62A—C12A—C72A—C72A^i	−94.8 (7)
C21A—C31A—C41A—O1A	−177.7 (4)	C22A—C12A—C72A—C82A	−90.5 (5)
O1A—C41A—C51A—C61A	178.5 (4)	C62A—C12A—C72A—C82A	84.9 (6)
C31A—C41A—C51A—C61A	−2.1 (8)	C72A^i—C72A—C82A—C92A	−107.1 (9)
C41A—C51A—C61A—C11A	0.9 (7)	C12A—C72A—C82A—C92A	73.3 (8)
C21A—C11A—C61A—C51A	−0.5 (6)	C63A—C13A—C23A—C33A	0.5 (5)
C71A—C11A—C61A—C51A	176.3 (4)	C73A—C13A—C23A—C33A	174.9 (10)
C21A—C11A—C71A—C71A^i	−73.1 (9)	C13A—C23A—C33A—C43A	−0.9 (8)
C61A—C11A—C71A—C71A^i	110.3 (8)	C23A—C33A—C43A—C53A	1.3 (11)
C21A—C11A—C71A—C81A	101.2 (5)	C33A—C43A—C53A—C63A	−1.4 (12)
C61A—C11A—C71A—C81A	−75.4 (6)	C23A—C13A—C63A—C53A	−0.6 (9)
C71A^i—C71A—C81A—C91A	95.6 (10)	C73A—C13A—C63A—C53A	−174.8 (11)
C11A—C71A—C81A—C91A	−78.9 (6)	C43A—C53A—C63A—C13A	1.1 (12)
C62A—C12A—C22A—C32A	0.1 (4)	C23A—C13A—C73A—C83A	72.8 (16)
C72A—C12A—C22A—C32A	175.6 (4)	C63A—C13A—C73A—C83A	−113.2 (13)
C12A—C22A—C32A—C42A	1.0 (6)	C23A—C13A—C73A—C73A^i	−114.1 (14)
C22A—C32A—C42A—C52A	−1.8 (8)	C63A—C13A—C73A—C73A^i	59.9 (17)
C32A—C42A—C52A—C62A	1.5 (9)	C13A—C73A—C83A—C93A	77.1 (19)
C42A—C52A—C62A—C12A	−0.4 (8)	C73A^i—C73A—C83A—C93A	−94 (2)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O11C^ii	0.96 (3)	1.65 (3)	2.590 (9)	169 (2)
O11B—H1B···O1A	0.82 (3)	1.97 (3)	2.798 (9)	177 (2)
O11C—H1C···O11B	0.82 (3)	1.86 (3)	2.678 (14)	168 (3)

Symmetry code: (ii) x−1, y, z.

(detw) diethylstilbestrol etanol solvate dihydrate (1/1/2)

Crystal data

C18H20O2·C2H6O·2(H2O)	Z = 2
Mr = 350.44	F(000) = 380
Triclinic, P1	Dx = 1.140 Mg m^−3
a = 7.7092 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9320 (5) Å	Cell parameters from 6108 reflections
c = 15.3466 (8) Å	θ = 2.6–38.0°
α = 93.797 (2)°	µ = 0.08 mm^−1
β = 100.629 (2)°	T = 150 K
γ = 98.866 (2)°	Needle, colourless
V = 1021.32 (9) Å^3	1.60 × 0.30 × 0.25 mm

Data collection

Siemens SMART CCD diffractometer	9755 independent reflections
Radiation source: fine-focus sealed tube	7414 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.013
Detector resolution: 8.3 pixels mm^-1	θmax = 38.0°, θmin = 2.6°
Sets of exposures each taken over 0.3° ω rotation scans	h = −11→13
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996)	k = −14→15
Tmin = 0.878, Tmax = 0.980	l = −25→26
15807 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0827P)^2 + 0.1207P] where P = (Fo^2 + 2Fc^2)/3
9755 reflections	(Δ/σ)max = 0.001
293 parameters	Δρmax = 0.54 e Å^−3
23 restraints	Δρmin = −0.34 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1A	0.43147 (10)	0.12891 (12)	0.11204 (4)	0.04440 (19)
H1A	0.528 (2)	0.171 (3)	0.1102 (12)	0.067*	0.702 (14)
H4A	0.3398	0.1044	0.0711	0.067*	0.298 (14)
C1A	0.29520 (9)	0.16948 (8)	0.36345 (4)	0.01912 (11)
C2A	0.43059 (10)	0.27481 (8)	0.34120 (5)	0.02203 (12)
H2A	0.4913	0.3569	0.3838	0.026*
C3A	0.47851 (10)	0.26229 (9)	0.25820 (5)	0.02586 (14)
H3A	0.5719	0.3344	0.2449	0.031*
C4A	0.38901 (11)	0.14376 (11)	0.19478 (5)	0.02782 (15)
C5A	0.25245 (11)	0.03881 (10)	0.21454 (5)	0.02865 (15)
H5A	0.1907	−0.0419	0.1712	0.034*
C6A	0.20630 (10)	0.05211 (9)	0.29774 (5)	0.02440 (13)
H6A	0.1123	−0.0200	0.3104	0.029*
C7A	0.24137 (8)	0.18338 (7)	0.45176 (4)	0.01820 (11)
C8A	0.04116 (9)	0.17230 (8)	0.44635 (5)	0.02155 (12)
H81A	0.0167	0.1774	0.5075	0.026*
H82A	−0.0201	0.0722	0.4154	0.026*
C9A	−0.03713 (11)	0.29773 (10)	0.39758 (6)	0.03163 (17)
H91A	−0.1662	0.2844	0.3962	0.047*
H92A	−0.0160	0.2920	0.3365	0.047*
H93A	0.0206	0.3973	0.4287	0.047*
O1'A	0.14751 (10)	0.26455 (8)	0.86354 (4)	0.03421 (14)
H1'A	0.099 (3)	0.340 (3)	0.8704 (16)	0.051*	0.670 (13)
H4'A	0.171 (6)	0.194 (4)	0.895 (3)	0.051*	0.330 (13)
C1'A	0.30627 (9)	0.21897 (7)	0.61778 (4)	0.01826 (11)
C2'A	0.22606 (10)	0.34224 (8)	0.64095 (5)	0.02199 (12)
H2'A	0.2073	0.4161	0.6000	0.026*
C3'A	0.17302 (10)	0.35937 (8)	0.72260 (5)	0.02348 (13)
H3'A	0.1183	0.4437	0.7368	0.028*
C4'A	0.20080 (10)	0.25203 (9)	0.78321 (5)	0.02294 (12)
C5'A	0.28365 (11)	0.12990 (9)	0.76263 (5)	0.02469 (13)
H5'A	0.3042	0.0573	0.8043	0.030*
C6'A	0.33628 (10)	0.11454 (8)	0.68101 (5)	0.02198 (12)
H6'A	0.3938	0.0315	0.6678	0.026*
C7'A	0.36139 (9)	0.19936 (7)	0.52996 (4)	0.01788 (11)
C8'A	0.55890 (9)	0.19300 (8)	0.53735 (5)	0.02065 (12)
H83A	0.5813	0.1648	0.4774	0.025*
H84A	0.5905	0.1123	0.5756	0.025*
C9'A	0.68050 (11)	0.34379 (10)	0.57615 (6)	0.02935 (15)
H94A	0.8059	0.3327	0.5792	0.044*
H95A	0.6613	0.3712	0.6361	0.044*
H96A	0.6520	0.4239	0.5379	0.044*
O1B	0.00106 (10)	0.50579 (9)	0.91081 (5)	0.03752 (16)	0.330 (12)
H3B	0.0664	0.5849	0.9003	0.056*	0.171 (13)
H1B	0.003 (5)	0.493 (4)	0.971 (2)	0.056*	0.50
H2B	0.036 (7)	0.415 (6)	0.890 (3)	0.056*	0.330 (13)
C11B	−0.1657 (5)	0.5329 (5)	0.8605 (6)	0.0288 (13)	0.330 (12)
H11B	−0.1460	0.5758	0.8046	0.035*	0.330 (12)
H12B	−0.2151	0.6073	0.8954	0.035*	0.330 (12)
C21B	−0.2940 (6)	0.3877 (5)	0.8397 (5)	0.0434 (11)*	0.330 (12)
H21B	−0.4075	0.4058	0.8048	0.065*	0.330 (12)
H22B	−0.3150	0.3468	0.8952	0.065*	0.330 (12)
H23B	−0.2445	0.3144	0.8052	0.065*	0.330 (12)
O12B	0.00106 (10)	0.50579 (9)	0.91081 (5)	0.03752 (16)	0.306 (13)
C12B	−0.1665 (6)	0.5224 (14)	0.8555 (7)	0.074 (5)	0.306 (13)
H13B	−0.1530	0.5196	0.7926	0.089*	0.306 (13)
H14B	−0.1963	0.6229	0.8724	0.089*	0.306 (13)
C22B	−0.3137 (7)	0.4026 (8)	0.8639 (9)	0.0449 (15)*	0.306 (13)
H24B	−0.4266	0.4244	0.8304	0.067*	0.306 (13)
H25B	−0.3211	0.3991	0.9268	0.067*	0.306 (13)
H26B	−0.2920	0.3041	0.8401	0.067*	0.306 (13)
O13B	0.00106 (10)	0.50579 (9)	0.91081 (5)	0.03752 (16)	0.208 (8)
C13B	−0.1805 (7)	0.480 (2)	0.8589 (6)	0.068 (4)*	0.208 (8)
H15B	−0.2022	0.3800	0.8239	0.082*	0.208 (8)
H16B	−0.1883	0.5584	0.8161	0.082*	0.208 (8)
C23B	−0.3261 (9)	0.4845 (18)	0.9089 (7)	0.069 (3)*	0.208 (8)
H27B	−0.4320	0.5074	0.8695	0.104*	0.208 (8)
H28B	−0.2872	0.5635	0.9592	0.104*	0.208 (8)
H29B	−0.3556	0.3854	0.9312	0.104*	0.208 (8)
O14B	0.00106 (10)	0.50579 (9)	0.91081 (5)	0.03752 (16)	0.153 (12)
C14B	−0.1736 (6)	0.5417 (11)	0.8774 (9)	0.033 (3)*	0.153 (12)
H17B	−0.1866	0.5486	0.8124	0.040*	0.153 (12)
H18B	−0.1797	0.6434	0.9052	0.040*	0.153 (12)
C24B	−0.3264 (8)	0.4327 (18)	0.8929 (12)	0.045 (3)*	0.153 (12)
H30B	−0.4301	0.4318	0.8449	0.067*	0.153 (12)
H31B	−0.3561	0.4632	0.9501	0.067*	0.153 (12)
H32C	−0.2947	0.3307	0.8938	0.067*	0.153 (12)
O1C	0.2276 (2)	0.76858 (14)	0.88800 (18)	0.0495 (6)	0.848 (9)
H13C	0.3389	0.7976	0.8919	0.074*	0.298 (14)
H11C	0.195 (3)	0.840 (3)	0.9119 (17)	0.074*	0.872 (17)
H12C	0.169 (3)	0.686 (3)	0.8994 (17)	0.074*	0.829 (13)
O2	0.2634 (13)	0.7634 (10)	0.9272 (10)	0.057 (2)*	0.152 (9)
O1D	0.15717 (10)	0.03391 (9)	0.97160 (5)	0.03421 (14)
H14D	0.1748	−0.0455	0.9426	0.051*	0.128 (17)
H11D	0.243 (3)	0.053 (3)	1.0113 (16)	0.051*	0.702 (14)
H12D	0.055 (4)	0.017 (4)	0.988 (2)	0.051*	0.50
H13D	0.154 (3)	0.106 (3)	0.9421 (17)	0.051*	0.670 (13)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0334 (3)	0.0785 (6)	0.0199 (2)	0.0052 (3)	0.0075 (2)	−0.0012 (3)
C1A	0.0175 (3)	0.0205 (3)	0.0188 (2)	0.0039 (2)	0.00156 (19)	0.0024 (2)
C2A	0.0211 (3)	0.0226 (3)	0.0219 (3)	0.0025 (2)	0.0038 (2)	0.0026 (2)
C3A	0.0226 (3)	0.0319 (3)	0.0230 (3)	0.0028 (3)	0.0049 (2)	0.0056 (3)
C4A	0.0238 (3)	0.0406 (4)	0.0188 (3)	0.0069 (3)	0.0028 (2)	0.0022 (3)
C5A	0.0259 (3)	0.0354 (4)	0.0212 (3)	0.0024 (3)	0.0005 (2)	−0.0038 (3)
C6A	0.0220 (3)	0.0267 (3)	0.0218 (3)	0.0002 (2)	0.0013 (2)	−0.0001 (2)
C7A	0.0167 (2)	0.0182 (2)	0.0194 (2)	0.00315 (19)	0.00253 (19)	0.00263 (19)
C8A	0.0167 (3)	0.0238 (3)	0.0237 (3)	0.0022 (2)	0.0027 (2)	0.0047 (2)
C9A	0.0217 (3)	0.0357 (4)	0.0407 (4)	0.0106 (3)	0.0058 (3)	0.0147 (3)
O1'A	0.0475 (4)	0.0368 (3)	0.0261 (3)	0.0160 (3)	0.0182 (3)	0.0080 (2)
C1'A	0.0168 (2)	0.0184 (2)	0.0192 (2)	0.00334 (19)	0.00217 (18)	0.00195 (19)
C2'A	0.0245 (3)	0.0207 (3)	0.0229 (3)	0.0074 (2)	0.0064 (2)	0.0046 (2)
C3'A	0.0266 (3)	0.0219 (3)	0.0243 (3)	0.0075 (2)	0.0080 (2)	0.0032 (2)
C4'A	0.0234 (3)	0.0256 (3)	0.0208 (3)	0.0047 (2)	0.0063 (2)	0.0029 (2)
C5'A	0.0288 (3)	0.0258 (3)	0.0222 (3)	0.0093 (3)	0.0065 (2)	0.0072 (2)
C6'A	0.0239 (3)	0.0214 (3)	0.0217 (3)	0.0074 (2)	0.0039 (2)	0.0039 (2)
C7'A	0.0170 (2)	0.0175 (2)	0.0191 (2)	0.00406 (19)	0.00245 (18)	0.00198 (19)
C8'A	0.0172 (3)	0.0229 (3)	0.0219 (3)	0.0056 (2)	0.00248 (19)	0.0009 (2)
C9'A	0.0201 (3)	0.0313 (4)	0.0333 (4)	0.0002 (3)	0.0030 (3)	−0.0050 (3)
O1B	0.0361 (3)	0.0404 (4)	0.0381 (3)	0.0127 (3)	0.0073 (3)	0.0041 (3)
C11B	0.030 (2)	0.0203 (19)	0.037 (3)	0.0035 (14)	0.0091 (18)	0.0033 (14)
O12B	0.0361 (3)	0.0404 (4)	0.0381 (3)	0.0127 (3)	0.0073 (3)	0.0041 (3)
C12B	0.051 (5)	0.136 (12)	0.047 (4)	0.060 (6)	−0.001 (3)	0.029 (4)
O13B	0.0361 (3)	0.0404 (4)	0.0381 (3)	0.0127 (3)	0.0073 (3)	0.0041 (3)
O14B	0.0361 (3)	0.0404 (4)	0.0381 (3)	0.0127 (3)	0.0073 (3)	0.0041 (3)
O1C	0.0530 (8)	0.0406 (6)	0.0601 (12)	0.0066 (4)	0.0265 (7)	0.0023 (5)
O1D	0.0321 (3)	0.0423 (4)	0.0290 (3)	0.0062 (3)	0.0077 (2)	0.0045 (3)

Geometric parameters (Å, º)

O1A—C4A	1.3716 (10)	C9'A—H95A	0.9800
O1A—H1A	0.79 (2)	C9'A—H96A	0.9800
O1A—H4A	0.8441	O1B—C11B	1.436 (3)
C1A—C2A	1.4009 (10)	O1B—H3B	0.8452
C1A—C6A	1.4033 (10)	O1B—H1B	0.94 (3)
C1A—C7A	1.4918 (9)	O1B—H2B	0.94 (6)
C2A—C3A	1.3924 (10)	C11B—C21B	1.482 (4)
C2A—H2A	0.9500	C11B—H11B	0.9900
C3A—C4A	1.3910 (11)	C11B—H12B	0.9900
C3A—H3A	0.9500	C21B—H21B	0.9800
C4A—C5A	1.3893 (12)	C21B—H22B	0.9800
C5A—C6A	1.3898 (11)	C21B—H23B	0.9800
C5A—H5A	0.9500	C12B—C22B	1.466 (5)
C6A—H6A	0.9500	C12B—H13B	0.9900
C7A—C7'A	1.3578 (9)	C12B—H14B	0.9900
C7A—C8A	1.5178 (9)	C22B—H24B	0.9800
C8A—C9A	1.5273 (11)	C22B—H25B	0.9800
C8A—H81A	0.9900	C22B—H26B	0.9800
C8A—H82A	0.9900	C13B—C23B	1.475 (5)
C9A—H91A	0.9800	C13B—H15B	0.9900
C9A—H92A	0.9800	C13B—H16B	0.9900
C9A—H93A	0.9800	C23B—H27B	0.9800
O1'A—C4'A	1.3725 (9)	C23B—H28B	0.9800
O1'A—H1'A	0.82 (3)	C23B—H29B	0.9800
O1'A—H4'A	0.846 (10)	C14B—C24B	1.474 (5)
C1'A—C2'A	1.4001 (9)	C14B—H17B	0.9900
C1'A—C6'A	1.4031 (9)	C14B—H18B	0.9900
C1'A—C7'A	1.4935 (9)	C24B—H30B	0.9800
C2'A—C3'A	1.3941 (10)	C24B—H31B	0.9800
C2'A—H2'A	0.9500	C24B—H32C	0.9800
C3'A—C4'A	1.3922 (10)	O1C—O2	0.621 (13)
C3'A—H3'A	0.9500	O1C—H13C	0.8474
C4'A—C5'A	1.3933 (10)	O1C—H11C	0.81 (3)
C5'A—C6'A	1.3909 (10)	O1C—H12C	0.85 (3)
C5'A—H5'A	0.9500	O2—H13C	0.8995
C6'A—H6'A	0.9500	O2—H11C	0.94 (3)
C7'A—C8'A	1.5160 (9)	O2—H12C	0.94 (3)
C8'A—C9'A	1.5317 (11)	O1D—H14D	0.8543
C8'A—H83A	0.9900	O1D—H11D	0.80 (2)
C8'A—H84A	0.9900	O1D—H12D	0.86 (3)
C9'A—H94A	0.9800	O1D—H13D	0.81 (3)
C4A—O1A—H1A	113.7 (14)	H94A—C9'A—H95A	109.5
C4A—O1A—H4A	112.4	C8'A—C9'A—H96A	109.5
H1A—O1A—H4A	130.0	H94A—C9'A—H96A	109.5
C2A—C1A—C6A	117.22 (6)	H95A—C9'A—H96A	109.5
C2A—C1A—C7A	122.01 (6)	C11B—O1B—H3B	97.5
C6A—C1A—C7A	120.73 (6)	C11B—O1B—H1B	116 (2)
C3A—C2A—C1A	121.71 (6)	H3B—O1B—H1B	116.0
C3A—C2A—H2A	119.1	C11B—O1B—H2B	114 (3)
C1A—C2A—H2A	119.1	H3B—O1B—H2B	112.6
C4A—C3A—C2A	119.69 (7)	H1B—O1B—H2B	102 (4)
C4A—C3A—H3A	120.2	O1B—C11B—C21B	109.4 (3)
C2A—C3A—H3A	120.2	O1B—C11B—H11B	109.8
O1A—C4A—C5A	118.89 (7)	C21B—C11B—H11B	109.8
O1A—C4A—C3A	121.23 (8)	O1B—C11B—H12B	109.8
C5A—C4A—C3A	119.87 (7)	C21B—C11B—H12B	109.8
C4A—C5A—C6A	119.92 (7)	H11B—C11B—H12B	108.2
C4A—C5A—H5A	120.0	C11B—C21B—H21B	109.5
C6A—C5A—H5A	120.0	C11B—C21B—H22B	109.5
C5A—C6A—C1A	121.58 (7)	H21B—C21B—H22B	109.5
C5A—C6A—H6A	119.2	C11B—C21B—H23B	109.5
C1A—C6A—H6A	119.2	H21B—C21B—H23B	109.5
C7'A—C7A—C1A	122.54 (6)	H22B—C21B—H23B	109.5
C7'A—C7A—C8A	123.23 (6)	C22B—C12B—H13B	109.1
C1A—C7A—C8A	114.19 (5)	C22B—C12B—H14B	109.1
C7A—C8A—C9A	113.36 (6)	H13B—C12B—H14B	107.9
C7A—C8A—H81A	108.9	C12B—C22B—H24B	109.5
C9A—C8A—H81A	108.9	C12B—C22B—H25B	109.5
C7A—C8A—H82A	108.9	H24B—C22B—H25B	109.5
C9A—C8A—H82A	108.9	C12B—C22B—H26B	109.5
H81A—C8A—H82A	107.7	H24B—C22B—H26B	109.5
C8A—C9A—H91A	109.5	H25B—C22B—H26B	109.5
C8A—C9A—H92A	109.5	C23B—C13B—H15B	108.1
H91A—C9A—H92A	109.5	C23B—C13B—H16B	108.1
C8A—C9A—H93A	109.5	H15B—C13B—H16B	107.3
H91A—C9A—H93A	109.5	C13B—C23B—H27B	109.5
H92A—C9A—H93A	109.5	C13B—C23B—H28B	109.5
C4'A—O1'A—H1'A	113.1 (17)	H27B—C23B—H28B	109.5
C4'A—O1'A—H4'A	113 (3)	C13B—C23B—H29B	109.5
H1'A—O1'A—H4'A	134 (4)	H27B—C23B—H29B	109.5
C2'A—C1'A—C6'A	117.48 (6)	H28B—C23B—H29B	109.5
C2'A—C1'A—C7'A	121.83 (6)	C24B—C14B—H17B	108.4
C6'A—C1'A—C7'A	120.68 (6)	C24B—C14B—H18B	108.4
C3'A—C2'A—C1'A	121.70 (6)	H17B—C14B—H18B	107.5
C3'A—C2'A—H2'A	119.2	C14B—C24B—H30B	109.5
C1'A—C2'A—H2'A	119.2	C14B—C24B—H31B	109.5
C4'A—C3'A—C2'A	119.53 (6)	H30B—C24B—H31B	109.5
C4'A—C3'A—H3'A	120.2	C14B—C24B—H32C	109.5
C2'A—C3'A—H3'A	120.2	H30B—C24B—H32C	109.5
O1'A—C4'A—C3'A	120.87 (7)	H31B—C24B—H32C	109.5
O1'A—C4'A—C5'A	119.15 (7)	O2—O1C—H13C	73.7
C3'A—C4'A—C5'A	119.98 (6)	O2—O1C—H11C	81.0 (18)
C6'A—C5'A—C4'A	119.83 (6)	H13C—O1C—H11C	103.9
C6'A—C5'A—H5'A	120.1	O2—O1C—H12C	77.5 (18)
C4'A—C5'A—H5'A	120.1	H13C—O1C—H12C	131.2
C5'A—C6'A—C1'A	121.45 (6)	H11C—O1C—H12C	110 (2)
C5'A—C6'A—H6'A	119.3	O1C—O2—H13C	64.7
C1'A—C6'A—H6'A	119.3	O1C—O2—H11C	58.2 (17)
C7A—C7'A—C1'A	121.88 (6)	H13C—O2—H11C	90.3
C7A—C7'A—C8'A	124.25 (6)	O1C—O2—H12C	62.2 (18)
C1'A—C7'A—C8'A	113.83 (5)	H13C—O2—H12C	114.5
C7'A—C8'A—C9'A	113.23 (6)	H11C—O2—H12C	92 (2)
C7'A—C8'A—H83A	108.9	H14D—O1D—H11D	103.7
C9'A—C8'A—H83A	108.9	H14D—O1D—H12D	110.2
C7'A—C8'A—H84A	108.9	H11D—O1D—H12D	116 (3)
C9'A—C8'A—H84A	108.9	H14D—O1D—H13D	112.5
H83A—C8'A—H84A	107.7	H11D—O1D—H13D	109 (2)
C8'A—C9'A—H94A	109.5	H12D—O1D—H13D	106 (3)
C8'A—C9'A—H95A	109.5
C6A—C1A—C2A—C3A	−1.45 (10)	C1'A—C2'A—C3'A—C4'A	0.30 (11)
C7A—C1A—C2A—C3A	−179.12 (6)	C2'A—C3'A—C4'A—O1'A	−178.98 (7)
C1A—C2A—C3A—C4A	0.86 (11)	C2'A—C3'A—C4'A—C5'A	1.02 (11)
C2A—C3A—C4A—O1A	179.31 (8)	O1'A—C4'A—C5'A—C6'A	179.15 (7)
C2A—C3A—C4A—C5A	0.06 (12)	C3'A—C4'A—C5'A—C6'A	−0.85 (12)
O1A—C4A—C5A—C6A	−179.59 (8)	C4'A—C5'A—C6'A—C1'A	−0.65 (12)
C3A—C4A—C5A—C6A	−0.33 (12)	C2'A—C1'A—C6'A—C5'A	1.90 (10)
C4A—C5A—C6A—C1A	−0.32 (12)	C7'A—C1'A—C6'A—C5'A	−179.12 (7)
C2A—C1A—C6A—C5A	1.18 (11)	C1A—C7A—C7'A—C1'A	177.67 (6)
C7A—C1A—C6A—C5A	178.88 (7)	C8A—C7A—C7'A—C1'A	−4.64 (10)
C2A—C1A—C7A—C7'A	−52.33 (9)	C1A—C7A—C7'A—C8'A	−4.84 (10)
C6A—C1A—C7A—C7'A	130.08 (7)	C8A—C7A—C7'A—C8'A	172.85 (6)
C2A—C1A—C7A—C8A	129.79 (7)	C2'A—C1'A—C7'A—C7A	−60.47 (9)
C6A—C1A—C7A—C8A	−47.80 (8)	C6'A—C1'A—C7'A—C7A	120.59 (7)
C7'A—C7A—C8A—C9A	120.71 (8)	C2'A—C1'A—C7'A—C8'A	121.79 (7)
C1A—C7A—C8A—C9A	−61.42 (8)	C6'A—C1'A—C7'A—C8'A	−57.14 (8)
C6'A—C1'A—C2'A—C3'A	−1.73 (10)	C7A—C7'A—C8'A—C9'A	115.42 (8)
C7'A—C1'A—C2'A—C3'A	179.31 (6)	C1'A—C7'A—C8'A—C9'A	−66.91 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O1C^i	0.79 (2)	1.87 (2)	2.6469 (14)	168 (2)
O1′A—H1′A···O1B	0.82 (3)	1.89 (3)	2.6998 (12)	168 (3)
O1B—H1B···O1B^ii	0.94 (3)	1.82 (3)	2.7494 (19)	172 (3)
O1C—H11C···O1D^iii	0.81 (3)	1.99 (3)	2.7942 (15)	170 (2)
O1C—H12C···O1B	0.85 (3)	1.94 (3)	2.7843 (14)	170 (2)
O1D—H11D···O1A^iv	0.80 (2)	1.92 (2)	2.7130 (13)	170 (2)
O1D—H12D···O1D^v	0.86 (3)	1.86 (3)	2.7195 (19)	175 (3)
O1D—H13D···O1′A	0.81 (4)	1.92 (4)	2.7302 (13)	175 (2)

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

(d1-prw) diethylstilbestrol 1-propanol solvate dihydrate (1/1/2)

Crystal data

C18H20O2·C3H8O·2(H2O)	Z = 2
Mr = 364.47	F(000) = 396
Triclinic, P1	Dx = 1.176 Mg m^−3
a = 7.7102 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9295 (2) Å	Cell parameters from 7925 reflections
c = 15.4299 (3) Å	θ = 1.4–30.5°
α = 94.337 (1)°	µ = 0.08 mm^−1
β = 100.071 (1)°	T = 150 K
γ = 98.291 (1)°	Plate, colourless
V = 1029.46 (4) Å^3	0.60 × 0.30 × 0.10 mm

Data collection

Siemens SMART CCD diffractometer	6159 independent reflections
Radiation source: fine-focus sealed tube	4739 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 8.3 pixels mm^-1	θmax = 30.5°, θmin = 1.4°
Sets of exposures each taken over 0.6° ω rotation scans	h = −11→10
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996)	k = −12→12
Tmin = 0.952, Tmax = 0.992	l = −22→22
15483 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0643P)^2 + 0.1839P] where P = (Fo^2 + 2Fc^2)/3
6159 reflections	(Δ/σ)max = 0.005
294 parameters	Δρmax = 0.34 e Å^−3
12 restraints	Δρmin = −0.23 e Å^−3

Special details

Refinement. Refinement of F² against ALL reflections.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1A	0.43522 (13)	0.13155 (12)	0.11266 (6)	0.0352 (2)
H1A	0.541 (4)	0.171 (3)	0.1115 (17)	0.053*	0.727 (14)
H4A	0.348 (10)	0.103 (8)	0.072 (5)	0.053*	0.273 (14)
C1A	0.29854 (12)	0.16990 (11)	0.36387 (6)	0.01791 (18)
C2A	0.43504 (13)	0.27327 (11)	0.34215 (7)	0.02002 (19)
H2A	0.4965	0.3539	0.3851	0.024*
C3A	0.48308 (13)	0.26119 (12)	0.25940 (7)	0.0223 (2)
H3A	0.5772	0.3321	0.2466	0.027*
C4A	0.39258 (14)	0.14478 (13)	0.19549 (7)	0.0232 (2)
C5A	0.25475 (14)	0.04177 (13)	0.21462 (7)	0.0249 (2)
H5A	0.1921	−0.0374	0.1710	0.030*
C6A	0.20880 (13)	0.05469 (12)	0.29761 (7)	0.0224 (2)
H6A	0.1142	−0.0163	0.3099	0.027*
C7A	0.24405 (12)	0.18395 (11)	0.45194 (6)	0.01727 (18)
C8A	0.04380 (12)	0.17335 (12)	0.44709 (7)	0.02046 (19)
H81A	0.0190	0.1801	0.5080	0.025*
H82A	−0.0163	0.0728	0.4168	0.025*
C9A	−0.03514 (15)	0.29780 (14)	0.39812 (9)	0.0303 (2)
H91A	−0.1638	0.2852	0.3973	0.045*
H92A	−0.0139	0.2902	0.3373	0.045*
H93A	0.0218	0.3978	0.4284	0.045*
O1'A	0.13575 (12)	0.26446 (11)	0.85977 (6)	0.02928 (18)
H1'A	0.088 (4)	0.338 (4)	0.8688 (18)	0.044*	0.639 (14)
H4'A	0.149 (6)	0.197 (6)	0.897 (4)	0.044*	0.361 (14)
C1'A	0.30458 (12)	0.21961 (11)	0.61671 (6)	0.01744 (18)
C2'A	0.22786 (13)	0.34528 (11)	0.64104 (7)	0.02064 (19)
H2'A	0.2133	0.4209	0.6014	0.025*
C3'A	0.17224 (13)	0.36230 (12)	0.72200 (7)	0.0220 (2)
H3'A	0.1210	0.4488	0.7373	0.026*
C4'A	0.19234 (13)	0.25165 (12)	0.78012 (7)	0.02017 (19)
C5'A	0.27030 (13)	0.12624 (12)	0.75792 (7)	0.0216 (2)
H5'A	0.2847	0.0508	0.7977	0.026*
C6'A	0.32689 (13)	0.11188 (11)	0.67760 (7)	0.02007 (19)
H6'A	0.3821	0.0270	0.6635	0.024*
C7'A	0.36219 (12)	0.20008 (11)	0.52933 (6)	0.01750 (18)
C8'A	0.55990 (12)	0.19327 (11)	0.53718 (7)	0.01960 (19)
H83A	0.5840	0.1632	0.4779	0.024*
H84A	0.5913	0.1138	0.5758	0.024*
C9'A	0.67935 (14)	0.34488 (13)	0.57502 (8)	0.0271 (2)
H94A	0.8048	0.3336	0.5783	0.041*
H95A	0.6587	0.3741	0.6344	0.041*
H96A	0.6508	0.4238	0.5365	0.041*
O1B	−0.00240 (11)	0.51321 (10)	0.91018 (6)	0.02892 (18)
H3B	0.0629	0.5923	0.8996	0.043*	0.139 (14)
H1B	−0.010 (5)	0.506 (4)	0.963 (2)	0.043*	0.50
H2B	0.047 (7)	0.442 (6)	0.894 (3)	0.043*	0.361 (14)
C11B	−0.1710 (10)	0.5376 (6)	0.8631 (6)	0.0371 (7)	0.709 (6)
H11B	−0.1524	0.5885	0.8099	0.045*	0.709 (6)
H12B	−0.2224	0.6068	0.9012	0.045*	0.709 (6)
C21B	−0.3038 (4)	0.3909 (3)	0.83476 (16)	0.0362 (6)	0.709 (6)
H21B	−0.2537	0.3216	0.7961	0.043*	0.709 (6)
H22B	−0.4156	0.4144	0.8002	0.043*	0.709 (6)
C31B	−0.3454 (10)	0.3113 (5)	0.9152 (5)	0.0569 (13)	0.709 (6)
H31B	−0.4332	0.2190	0.8951	0.085*	0.709 (6)
H32B	−0.3940	0.3801	0.9538	0.085*	0.709 (6)
H33B	−0.2357	0.2840	0.9481	0.085*	0.709 (6)
C12B	−0.1694 (13)	0.5288 (11)	0.8492 (5)	0.0371 (7)	0.183 (5)
H13B	−0.1496	0.5226	0.7875	0.045*	0.183 (5)
H14B	−0.2036	0.6292	0.8635	0.045*	0.183 (5)
C22B	−0.3188 (15)	0.4025 (11)	0.8584 (7)	0.0362 (6)	0.183 (5)
H23B	−0.2691	0.3077	0.8686	0.043*	0.183 (5)
H24B	−0.4084	0.3829	0.8028	0.043*	0.183 (5)
C32B	−0.4098 (12)	0.4457 (12)	0.9355 (6)	0.061 (3)*	0.183 (5)
H34B	−0.5088	0.3649	0.9381	0.091*	0.183 (5)
H35B	−0.4557	0.5412	0.9265	0.091*	0.183 (5)
H36B	−0.3231	0.4585	0.9912	0.091*	0.183 (5)
C13B	−0.180 (6)	0.535 (4)	0.856 (4)	0.0371 (7)	0.110 (5)
H13A	−0.1996	0.4800	0.7965	0.045*	0.110 (5)
H13C	−0.1822	0.6445	0.8502	0.045*	0.110 (5)
C23B	−0.326 (2)	0.4725 (18)	0.9056 (13)	0.062 (5)*	0.110 (5)
H23A	−0.4422	0.4949	0.8756	0.074*	0.110 (5)
H23C	−0.3001	0.5235	0.9667	0.074*	0.110 (5)
C33B	−0.337 (5)	0.300 (2)	0.909 (3)	0.030*	0.110 (5)
H33A	−0.4335	0.2623	0.9387	0.045*	0.110 (5)
H33C	−0.2234	0.2781	0.9408	0.045*	0.110 (5)
H33D	−0.3601	0.2495	0.8481	0.045*	0.110 (5)
O1C	0.21529 (14)	0.77704 (13)	0.87526 (7)	0.0390 (2)
H13CC	0.3266	0.8061	0.8791	0.058*	0.273 (14)
H11C	0.183 (3)	0.848 (3)	0.9081 (16)	0.058*	0.866 (18)
H12C	0.158 (3)	0.698 (3)	0.8914 (15)	0.058*	0.861 (14)
O1D	0.15756 (13)	0.04004 (11)	0.97133 (6)	0.03125 (19)
H14D	0.1751	−0.0394	0.9423	0.047*	0.134 (18)
H11D	0.246 (4)	0.066 (3)	1.0117 (19)	0.047*	0.727 (14)
H12D	0.056 (5)	0.016 (4)	0.987 (3)	0.047*	0.50
H13D	0.155 (4)	0.110 (4)	0.944 (2)	0.047*	0.639 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0283 (4)	0.0567 (6)	0.0188 (4)	0.0005 (4)	0.0070 (3)	−0.0015 (4)
C1A	0.0164 (4)	0.0193 (4)	0.0184 (4)	0.0044 (3)	0.0023 (3)	0.0032 (3)
C2A	0.0192 (4)	0.0192 (4)	0.0207 (5)	0.0021 (3)	0.0024 (3)	0.0010 (3)
C3A	0.0198 (4)	0.0245 (5)	0.0225 (5)	0.0014 (4)	0.0046 (4)	0.0042 (4)
C4A	0.0209 (5)	0.0306 (5)	0.0184 (5)	0.0051 (4)	0.0040 (4)	0.0023 (4)
C5A	0.0231 (5)	0.0274 (5)	0.0212 (5)	0.0003 (4)	0.0011 (4)	−0.0025 (4)
C6A	0.0192 (4)	0.0241 (5)	0.0221 (5)	−0.0004 (4)	0.0027 (4)	0.0017 (4)
C7A	0.0168 (4)	0.0159 (4)	0.0196 (4)	0.0028 (3)	0.0042 (3)	0.0029 (3)
C8A	0.0158 (4)	0.0232 (5)	0.0222 (5)	0.0020 (3)	0.0033 (3)	0.0038 (4)
C9A	0.0204 (5)	0.0335 (6)	0.0399 (6)	0.0096 (4)	0.0054 (4)	0.0127 (5)
O1'A	0.0387 (5)	0.0316 (4)	0.0233 (4)	0.0121 (4)	0.0148 (3)	0.0065 (3)
C1'A	0.0152 (4)	0.0189 (4)	0.0177 (4)	0.0021 (3)	0.0022 (3)	0.0018 (3)
C2'A	0.0227 (5)	0.0194 (4)	0.0215 (5)	0.0061 (3)	0.0051 (4)	0.0051 (4)
C3'A	0.0238 (5)	0.0198 (5)	0.0243 (5)	0.0066 (4)	0.0073 (4)	0.0029 (4)
C4'A	0.0186 (4)	0.0236 (5)	0.0186 (4)	0.0025 (3)	0.0048 (3)	0.0025 (4)
C5'A	0.0227 (5)	0.0216 (5)	0.0215 (5)	0.0051 (4)	0.0038 (4)	0.0066 (4)
C6'A	0.0209 (4)	0.0183 (4)	0.0213 (5)	0.0053 (3)	0.0029 (3)	0.0026 (3)
C7'A	0.0176 (4)	0.0159 (4)	0.0196 (4)	0.0041 (3)	0.0040 (3)	0.0024 (3)
C8'A	0.0171 (4)	0.0214 (5)	0.0207 (5)	0.0057 (3)	0.0024 (3)	0.0015 (4)
C9'A	0.0197 (5)	0.0292 (5)	0.0298 (6)	0.0001 (4)	0.0030 (4)	−0.0033 (4)
O1B	0.0245 (4)	0.0305 (4)	0.0320 (4)	0.0056 (3)	0.0050 (3)	0.0033 (3)
C11B	0.0298 (9)	0.0373 (7)	0.0442 (17)	0.0087 (6)	0.0012 (11)	0.0117 (8)
C21B	0.0319 (9)	0.0462 (10)	0.0251 (14)	−0.0025 (7)	−0.0046 (9)	0.0096 (9)
C31B	0.0438 (18)	0.067 (2)	0.048 (2)	−0.0197 (15)	−0.0047 (13)	0.0161 (17)
C12B	0.0298 (9)	0.0373 (7)	0.0442 (17)	0.0087 (6)	0.0012 (11)	0.0117 (8)
C22B	0.0319 (9)	0.0462 (10)	0.0251 (14)	−0.0025 (7)	−0.0046 (9)	0.0096 (9)
C13B	0.0298 (9)	0.0373 (7)	0.0442 (17)	0.0087 (6)	0.0012 (11)	0.0117 (8)
O1C	0.0412 (5)	0.0356 (5)	0.0430 (5)	0.0018 (4)	0.0187 (4)	0.0051 (4)
O1D	0.0287 (4)	0.0368 (5)	0.0278 (4)	0.0037 (3)	0.0053 (3)	0.0038 (4)

Geometric parameters (Å, º)

O1A—C4A	1.3751 (13)	C9'A—H96A	0.9800
O1A—H1A	0.85 (3)	O1B—C11B	1.428 (9)
O1A—H4A	0.83 (8)	O1B—C12B	1.486 (10)
C1A—C2A	1.4007 (14)	O1B—C13B	1.52 (6)
C1A—C6A	1.4038 (14)	O1B—H3B	0.8499
C1A—C7A	1.4927 (14)	O1B—H1B	0.83 (3)
C2A—C3A	1.3910 (14)	O1B—H2B	0.83 (6)
C2A—H2A	0.9500	C11B—C21B	1.525 (6)
C3A—C4A	1.3911 (14)	C11B—H11B	0.9900
C3A—H3A	0.9500	C11B—H12B	0.9900
C4A—C5A	1.3898 (15)	C21B—C31B	1.535 (6)
C5A—C6A	1.3881 (15)	C21B—H21B	0.9900
C5A—H5A	0.9500	C21B—H22B	0.9900
C6A—H6A	0.9500	C31B—H31B	0.9800
C7A—C7'A	1.3535 (13)	C31B—H32B	0.9800
C7A—C8A	1.5215 (13)	C31B—H33B	0.9800
C8A—C9A	1.5289 (15)	C12B—C22B	1.526 (6)
C8A—H81A	0.9900	C12B—H13B	0.9900
C8A—H82A	0.9900	C12B—H14B	0.9900
C9A—H91A	0.9800	C22B—C32B	1.535 (6)
C9A—H92A	0.9800	C22B—H23B	0.9900
C9A—H93A	0.9800	C22B—H24B	0.9900
O1'A—C4'A	1.3764 (13)	C32B—H34B	0.9800
O1'A—H1'A	0.81 (3)	C32B—H35B	0.9800
O1'A—H4'A	0.87 (6)	C32B—H36B	0.9800
C1'A—C2'A	1.3984 (14)	C13B—C23B	1.525 (6)
C1'A—C6'A	1.4020 (13)	C13B—H13A	0.9900
C1'A—C7'A	1.4974 (13)	C13B—H13C	0.9900
C2'A—C3'A	1.3946 (14)	C23B—C33B	1.535 (6)
C2'A—H2'A	0.9500	C23B—H23A	0.9900
C3'A—C4'A	1.3908 (14)	C23B—H23C	0.9900
C3'A—H3'A	0.9500	C33B—H33A	0.9800
C4'A—C5'A	1.3931 (14)	C33B—H33C	0.9800
C5'A—C6'A	1.3870 (14)	C33B—H33D	0.9800
C5'A—H5'A	0.9500	O1C—H13CC	0.8505
C6'A—H6'A	0.9500	O1C—H11C	0.87 (3)
C7'A—C8'A	1.5183 (13)	O1C—H12C	0.86 (3)
C8'A—C9'A	1.5345 (15)	O1D—H14D	0.8501
C8'A—H83A	0.9900	O1D—H11D	0.83 (3)
C8'A—H84A	0.9900	O1D—H12D	0.87 (3)
C9'A—H94A	0.9800	O1D—H13D	0.78 (4)
C9'A—H95A	0.9800
C4A—O1A—H1A	113.6 (18)	C11B—O1B—C12B	8.6 (6)
C4A—O1A—H4A	114 (5)	C11B—O1B—C13B	3 (2)
H1A—O1A—H4A	131 (5)	C12B—O1B—C13B	6.0 (19)
C2A—C1A—C6A	117.04 (9)	C11B—O1B—H3B	99.4
C2A—C1A—C7A	122.11 (9)	C12B—O1B—H3B	98.1
C6A—C1A—C7A	120.80 (9)	C13B—O1B—H3B	99.4
C3A—C2A—C1A	121.85 (9)	C11B—O1B—H1B	109 (3)
C3A—C2A—H2A	119.1	C12B—O1B—H1B	116 (3)
C1A—C2A—H2A	119.1	C13B—O1B—H1B	111 (3)
C2A—C3A—C4A	119.64 (9)	H3B—O1B—H1B	116.2
C2A—C3A—H3A	120.2	C11B—O1B—H2B	121 (3)
C4A—C3A—H3A	120.2	C12B—O1B—H2B	114 (3)
O1A—C4A—C5A	119.23 (10)	C13B—O1B—H2B	119 (4)
O1A—C4A—C3A	120.91 (10)	H3B—O1B—H2B	104.2
C5A—C4A—C3A	119.85 (10)	H1B—O1B—H2B	107 (4)
C6A—C5A—C4A	119.90 (9)	O1B—C11B—C21B	113.1 (4)
C6A—C5A—H5A	120.0	O1B—C11B—H11B	109.0
C4A—C5A—H5A	120.0	C21B—C11B—H11B	109.0
C5A—C6A—C1A	121.69 (9)	O1B—C11B—H12B	109.0
C5A—C6A—H6A	119.2	C21B—C11B—H12B	109.0
C1A—C6A—H6A	119.2	H11B—C11B—H12B	107.8
C7'A—C7A—C1A	122.83 (8)	C11B—C21B—C31B	111.2 (4)
C7'A—C7A—C8A	122.99 (9)	C11B—C21B—H21B	109.4
C1A—C7A—C8A	114.15 (8)	C31B—C21B—H21B	109.4
C7A—C8A—C9A	113.27 (8)	C11B—C21B—H22B	109.4
C7A—C8A—H81A	108.9	C31B—C21B—H22B	109.4
C9A—C8A—H81A	108.9	H21B—C21B—H22B	108.0
C7A—C8A—H82A	108.9	O1B—C12B—C22B	109.8 (7)
C9A—C8A—H82A	108.9	O1B—C12B—H13B	109.7
H81A—C8A—H82A	107.7	C22B—C12B—H13B	109.7
C8A—C9A—H91A	109.5	O1B—C12B—H14B	109.7
C8A—C9A—H92A	109.5	C22B—C12B—H14B	109.7
H91A—C9A—H92A	109.5	H13B—C12B—H14B	108.2
C8A—C9A—H93A	109.5	C12B—C22B—C32B	111.2 (4)
H91A—C9A—H93A	109.5	C12B—C22B—H23B	109.4
H92A—C9A—H93A	109.5	C32B—C22B—H23B	109.4
C4'A—O1'A—H1'A	116 (2)	C12B—C22B—H24B	109.4
C4'A—O1'A—H4'A	122 (3)	C32B—C22B—H24B	109.4
H1'A—O1'A—H4'A	123 (4)	H23B—C22B—H24B	108.0
C2'A—C1'A—C6'A	117.50 (9)	C22B—C32B—H34B	109.5
C2'A—C1'A—C7'A	121.71 (9)	C22B—C32B—H35B	109.5
C6'A—C1'A—C7'A	120.79 (8)	H34B—C32B—H35B	109.5
C3'A—C2'A—C1'A	121.62 (9)	C22B—C32B—H36B	109.5
C3'A—C2'A—H2'A	119.2	H34B—C32B—H36B	109.5
C1'A—C2'A—H2'A	119.2	H35B—C32B—H36B	109.5
C4'A—C3'A—C2'A	119.52 (9)	O1B—C13B—C23B	107 (3)
C4'A—C3'A—H3'A	120.2	O1B—C13B—H13A	110.2
C2'A—C3'A—H3'A	120.2	C23B—C13B—H13A	110.2
O1'A—C4'A—C3'A	120.65 (9)	O1B—C13B—H13C	110.2
O1'A—C4'A—C5'A	119.36 (9)	C23B—C13B—H13C	110.2
C3'A—C4'A—C5'A	119.98 (9)	H13A—C13B—H13C	108.5
C6'A—C5'A—C4'A	119.80 (9)	C13B—C23B—C33B	111.2 (4)
C6'A—C5'A—H5'A	120.1	C13B—C23B—H23A	109.4
C4'A—C5'A—H5'A	120.1	C33B—C23B—H23A	109.4
C5'A—C6'A—C1'A	121.55 (9)	C13B—C23B—H23C	109.4
C5'A—C6'A—H6'A	119.2	C33B—C23B—H23C	109.4
C1'A—C6'A—H6'A	119.2	H23A—C23B—H23C	108.0
C7A—C7'A—C1'A	121.68 (8)	C23B—C33B—H33A	109.5
C7A—C7'A—C8'A	124.62 (9)	C23B—C33B—H33C	109.5
C1'A—C7'A—C8'A	113.65 (8)	H33A—C33B—H33C	109.5
C7'A—C8'A—C9'A	113.20 (8)	C23B—C33B—H33D	109.5
C7'A—C8'A—H83A	108.9	H33A—C33B—H33D	109.5
C9'A—C8'A—H83A	108.9	H33C—C33B—H33D	109.5
C7'A—C8'A—H84A	108.9	H13CC—O1C—H11C	103.8
C9'A—C8'A—H84A	108.9	H13CC—O1C—H12C	130.8
H83A—C8'A—H84A	107.8	H11C—O1C—H12C	100 (2)
C8'A—C9'A—H94A	109.5	H14D—O1D—H11D	107.0
C8'A—C9'A—H95A	109.5	H14D—O1D—H12D	105.8
H94A—C9'A—H95A	109.5	H11D—O1D—H12D	117 (3)
C8'A—C9'A—H96A	109.5	H14D—O1D—H13D	112.9
H94A—C9'A—H96A	109.5	H11D—O1D—H13D	104 (3)
H95A—C9'A—H96A	109.5	H12D—O1D—H13D	110 (3)
C6A—C1A—C2A—C3A	−1.38 (14)	C4'A—C5'A—C6'A—C1'A	−1.25 (15)
C7A—C1A—C2A—C3A	−178.83 (9)	C2'A—C1'A—C6'A—C5'A	1.94 (14)
C1A—C2A—C3A—C4A	0.81 (15)	C7'A—C1'A—C6'A—C5'A	−178.39 (9)
C2A—C3A—C4A—O1A	178.92 (10)	C1A—C7A—C7'A—C1'A	177.73 (8)
C2A—C3A—C4A—C5A	0.16 (16)	C8A—C7A—C7'A—C1'A	−4.33 (14)
O1A—C4A—C5A—C6A	−179.27 (10)	C1A—C7A—C7'A—C8'A	−5.16 (15)
C3A—C4A—C5A—C6A	−0.49 (16)	C8A—C7A—C7'A—C8'A	172.77 (9)
C4A—C5A—C6A—C1A	−0.13 (16)	C2'A—C1'A—C7'A—C7A	−62.71 (13)
C2A—C1A—C6A—C5A	1.04 (15)	C6'A—C1'A—C7'A—C7A	117.64 (11)
C7A—C1A—C6A—C5A	178.52 (9)	C2'A—C1'A—C7'A—C8'A	119.90 (10)
C2A—C1A—C7A—C7'A	−51.03 (14)	C6'A—C1'A—C7'A—C8'A	−59.76 (12)
C6A—C1A—C7A—C7'A	131.62 (10)	C7A—C7'A—C8'A—C9'A	114.65 (11)
C2A—C1A—C7A—C8A	130.87 (10)	C1'A—C7'A—C8'A—C9'A	−68.04 (11)
C6A—C1A—C7A—C8A	−46.48 (12)	C12B—O1B—C11B—C21B	73.4 (17)
C7'A—C7A—C8A—C9A	121.34 (11)	C13B—O1B—C11B—C21B	65 (21)
C1A—C7A—C8A—C9A	−60.56 (12)	O1B—C11B—C21B—C31B	61.7 (6)
C6'A—C1'A—C2'A—C3'A	−1.16 (15)	C11B—O1B—C12B—C22B	−77.5 (12)
C7'A—C1'A—C2'A—C3'A	179.18 (9)	C13B—O1B—C12B—C22B	−74 (12)
C1'A—C2'A—C3'A—C4'A	−0.32 (15)	O1B—C12B—C22B—C32B	84.6 (12)
C2'A—C3'A—C4'A—O1'A	−178.89 (9)	C11B—O1B—C13B—C23B	−56 (20)
C2'A—C3'A—C4'A—C5'A	1.07 (15)	C12B—O1B—C13B—C23B	136 (14)
O1'A—C4'A—C5'A—C6'A	179.66 (9)	O1B—C13B—C23B—C33B	−65 (4)
C3'A—C4'A—C5'A—C6'A	−0.30 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1′A—H1′A···O1B	0.81 (3)	1.91 (3)	2.7173 (10)	170 (3)
O1B—H1B···O1B^i	0.83 (3)	1.97 (3)	2.7940 (16)	173 (4)
O1C—H11C···O1D^ii	0.87 (3)	1.96 (3)	2.8136 (15)	165 (2)
O1C—H12C···O1B	0.86 (3)	1.99 (3)	2.8330 (14)	170 (2)
O1D—H11D···O1A^iii	0.83 (3)	1.93 (3)	2.7568 (10)	174 (2)
O1D—H12D···O1D^iv	0.87 (3)	1.89 (3)	2.7466 (15)	177 (4)
O1D—H13D···O1′A	0.78 (4)	1.97 (3)	2.7431 (10)	172 (3)

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

(dmetw) diethylstilbestrol methanol solvate hydrate (1/1/0.79)

Crystal data

C18H20O2·CH4O·0.79(H2O)	Z = 2
Mr = 314.60	F(000) = 348
Triclinic, P1	Dx = 1.237 Mg m^−3
a = 7.5712 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1543 (7) Å	Cell parameters from 5992 reflections
c = 13.5964 (10) Å	θ = 2.8–38.0°
α = 73.691 (3)°	µ = 0.08 mm^−1
β = 75.460 (3)°	T = 150 K
γ = 80.517 (3)°	Plate, colourless
V = 870.95 (12) Å^3	1.20 × 1.10 × 0.20 mm

Data collection

Siemens SMART CCD diffractometer	8261 independent reflections
Radiation source: fine-focus sealed tube	6630 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
Detector resolution: 8.3 pixels mm^-1	θmax = 38.0°, θmin = 2.8°
Sets of exposures each taken over 0.3° ω rotation scans	h = −13→13
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996)	k = −15→15
Tmin = 0.907, Tmax = 0.984	l = −22→23
13311 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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.188	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0896P)^2 + 0.2731P] where P = (Fo^2 + 2Fc^2)/3
8261 reflections	(Δ/σ)max = 0.007
287 parameters	Δρmax = 0.64 e Å^−3
22 restraints	Δρmin = −0.42 e Å^−3

Special details

Refinement. Refinement of F² against ALL reflections.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1A	0.38879 (19)	0.68424 (15)	0.97162 (8)	0.0483 (3)	0.924 (3)
H1A	0.340 (4)	0.759 (3)	0.996 (2)	0.072*	0.924 (3)
C1A	0.2765 (2)	0.76572 (18)	0.67354 (8)	0.02096 (18)	0.924 (3)
C2A	0.40080 (19)	0.64414 (14)	0.71081 (9)	0.0277 (2)	0.924 (3)
H2A	0.4609	0.5772	0.6677	0.033*	0.924 (3)
C3A	0.4384 (2)	0.61917 (16)	0.80978 (9)	0.0339 (3)	0.924 (3)
H3A	0.5246	0.5369	0.8332	0.041*	0.924 (3)
C4A	0.34952 (19)	0.71486 (15)	0.87397 (8)	0.0322 (3)	0.924 (3)
C5A	0.22174 (18)	0.83549 (14)	0.83987 (8)	0.0295 (2)	0.924 (3)
H5A	0.1592	0.9002	0.8841	0.035*	0.924 (3)
C6A	0.18729 (17)	0.85971 (13)	0.74044 (8)	0.02514 (19)	0.924 (3)
H6A	0.1010	0.9421	0.7173	0.030*	0.924 (3)
C7A	0.2322 (3)	0.7921 (2)	0.56848 (13)	0.01972 (18)	0.924 (3)
O12A	0.4754 (16)	0.6189 (13)	0.9635 (6)	0.040 (3)*	0.076 (3)
C12A	0.305 (2)	0.7396 (17)	0.6785 (8)	0.023 (4)*	0.076 (3)
C22A	0.428 (2)	0.6107 (14)	0.7049 (7)	0.023*	0.076 (3)
H22A	0.4758	0.5488	0.6567	0.028*	0.076 (3)
C32A	0.4829 (15)	0.5710 (11)	0.8004 (6)	0.023 (2)*	0.076 (3)
H32A	0.5667	0.4830	0.8168	0.027*	0.076 (3)
C42A	0.4145 (14)	0.6604 (11)	0.8713 (6)	0.023 (2)*	0.076 (3)
C52A	0.2879 (13)	0.7879 (9)	0.8484 (6)	0.019 (2)*	0.076 (3)
H52A	0.2371	0.8470	0.8980	0.022*	0.076 (3)
C62A	0.237 (2)	0.8273 (14)	0.7520 (8)	0.035 (4)*	0.076 (3)
H62A	0.1543	0.9159	0.7356	0.042*	0.076 (3)
C72A	0.248 (6)	0.785 (4)	0.5758 (17)	0.023*	0.076 (3)
C8A	0.03040 (12)	0.79683 (10)	0.57310 (7)	0.02440 (16)
H81A	0.0105	0.8224	0.5007	0.029*
H82A	−0.0372	0.8790	0.6064	0.029*
C9A	−0.04725 (16)	0.64563 (14)	0.63444 (10)	0.0366 (2)
H91A	−0.1798	0.6569	0.6389	0.055*
H92A	−0.0234	0.6175	0.7053	0.055*
H93A	0.0116	0.5655	0.5985	0.055*
O1'A	0.21173 (15)	0.90705 (13)	0.07526 (6)	0.0439 (2)
H1'A	0.220 (3)	1.002 (3)	0.0411 (18)	0.066*
C1'A	0.31709 (11)	0.83955 (9)	0.37368 (6)	0.02002 (13)
C2'A	0.24461 (14)	0.72890 (10)	0.34674 (7)	0.02500 (16)
H2'A	0.2189	0.6353	0.3974	0.030*
C3'A	0.20913 (15)	0.75267 (12)	0.24743 (7)	0.02890 (18)
H3'A	0.1595	0.6760	0.2309	0.035*
C4'A	0.24644 (15)	0.88870 (13)	0.17280 (7)	0.02943 (18)
C5'A	0.31815 (15)	1.00103 (12)	0.19762 (8)	0.03071 (19)
H5'A	0.3426	1.0948	0.1469	0.037*
C6'A	0.35394 (13)	0.97549 (10)	0.29682 (7)	0.02506 (16)
H6'A	0.4046	1.0521	0.3128	0.030*
C7'A	0.36186 (11)	0.81379 (9)	0.47860 (6)	0.01956 (13)
C8'A	0.56361 (12)	0.81871 (10)	0.47235 (7)	0.02272 (15)
H83A	0.5811	0.8156	0.5427	0.027*
H84A	0.6030	0.9164	0.4241	0.027*
C9'A	0.68430 (14)	0.68584 (13)	0.43398 (8)	0.03068 (19)
H94A	0.8135	0.6976	0.4271	0.046*
H95A	0.6638	0.6858	0.3656	0.046*
H96A	0.6529	0.5890	0.4846	0.046*
O11B	0.7205 (5)	0.8099 (2)	0.03993 (12)	0.0584 (7)	0.694 (6)
H11B	0.7598	0.7381	0.0092	0.088*	0.694 (6)
C11B	0.7445 (6)	0.7648 (3)	0.14501 (17)	0.0487 (7)	0.694 (6)
H12B	0.8429	0.8174	0.1506	0.073*	0.694 (6)
H13B	0.7768	0.6540	0.1649	0.073*	0.694 (6)
H14B	0.6301	0.7921	0.1920	0.073*	0.694 (6)
O12B	0.8028 (17)	0.8233 (8)	0.0358 (5)	0.0347 (15)*	0.158 (5)
C12B	0.861 (6)	0.6653 (15)	0.070 (3)	0.205 (18)*	0.158 (5)
H15B	0.9949	0.6485	0.0476	0.308*	0.158 (5)
H16B	0.8032	0.6058	0.0397	0.308*	0.158 (5)
H17B	0.8262	0.6328	0.1469	0.308*	0.158 (5)
O13B	0.8709 (17)	0.8367 (10)	0.0399 (7)	0.054 (2)*	0.149 (6)
C13B	0.7856 (18)	0.7487 (15)	0.1395 (7)	0.035 (3)*	0.149 (6)
H18B	0.8794	0.6974	0.1795	0.052*	0.149 (6)
H19B	0.7199	0.6719	0.1298	0.052*	0.149 (6)
H20B	0.6989	0.8162	0.1779	0.052*	0.149 (6)
O11C	0.154 (3)	0.4163 (10)	0.0567 (5)	0.063 (3)	0.34 (2)
H11C	0.2186	0.4912	0.0328	0.094*	0.34 (2)
H12C	0.0681	0.4620	0.0256	0.094*	0.34 (2)
O12C	0.0499 (11)	0.4965 (9)	0.0499 (5)	0.052 (2)*	0.174 (6)
O13C	0.127 (3)	0.418 (3)	0.127 (2)	0.045 (8)*	0.044 (5)
O14C	0.217 (2)	0.3969 (14)	0.0579 (10)	0.025 (6)*	0.11 (3)
O15C	0.240 (5)	0.388 (3)	0.043 (3)	0.070*	0.13 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0654 (8)	0.0577 (7)	0.0227 (4)	−0.0043 (6)	−0.0206 (4)	−0.0028 (4)
C1A	0.0233 (5)	0.0217 (4)	0.0172 (4)	−0.0064 (4)	−0.0043 (3)	−0.0015 (3)
C2A	0.0318 (5)	0.0263 (5)	0.0220 (4)	−0.0012 (4)	−0.0071 (4)	−0.0015 (3)
C3A	0.0393 (6)	0.0341 (6)	0.0245 (4)	0.0004 (5)	−0.0120 (4)	0.0011 (4)
C4A	0.0402 (6)	0.0368 (6)	0.0194 (4)	−0.0092 (5)	−0.0103 (4)	−0.0002 (4)
C5A	0.0360 (6)	0.0337 (5)	0.0204 (4)	−0.0065 (4)	−0.0071 (4)	−0.0068 (3)
C6A	0.0289 (5)	0.0271 (4)	0.0203 (4)	−0.0048 (4)	−0.0059 (3)	−0.0057 (3)
C7A	0.0222 (7)	0.0196 (4)	0.0172 (4)	−0.0052 (3)	−0.0045 (3)	−0.0025 (4)
C8A	0.0224 (3)	0.0250 (3)	0.0242 (3)	−0.0037 (3)	−0.0047 (3)	−0.0032 (3)
C9A	0.0288 (4)	0.0349 (5)	0.0422 (6)	−0.0132 (4)	−0.0090 (4)	0.0034 (4)
O1'A	0.0563 (6)	0.0572 (6)	0.0209 (3)	−0.0162 (5)	−0.0175 (3)	−0.0003 (3)
C1'A	0.0221 (3)	0.0201 (3)	0.0178 (3)	−0.0043 (2)	−0.0052 (2)	−0.0028 (2)
C2'A	0.0333 (4)	0.0220 (3)	0.0216 (3)	−0.0079 (3)	−0.0099 (3)	−0.0021 (3)
C3'A	0.0383 (5)	0.0291 (4)	0.0235 (4)	−0.0090 (4)	−0.0123 (3)	−0.0052 (3)
C4'A	0.0333 (4)	0.0370 (5)	0.0188 (3)	−0.0078 (4)	−0.0097 (3)	−0.0022 (3)
C5'A	0.0370 (5)	0.0310 (4)	0.0224 (4)	−0.0118 (4)	−0.0102 (3)	0.0042 (3)
C6'A	0.0301 (4)	0.0229 (3)	0.0221 (3)	−0.0084 (3)	−0.0075 (3)	−0.0006 (3)
C7'A	0.0228 (3)	0.0187 (3)	0.0177 (3)	−0.0049 (2)	−0.0049 (2)	−0.0035 (2)
C8'A	0.0232 (3)	0.0253 (3)	0.0208 (3)	−0.0065 (3)	−0.0052 (3)	−0.0048 (3)
C9'A	0.0268 (4)	0.0357 (5)	0.0305 (4)	0.0005 (3)	−0.0077 (3)	−0.0107 (4)
O11B	0.0724 (18)	0.0617 (11)	0.0295 (6)	0.0006 (10)	−0.0153 (8)	0.0067 (6)
C11B	0.069 (2)	0.0367 (10)	0.0285 (8)	0.0092 (12)	−0.0090 (9)	0.0009 (7)
O11C	0.092 (10)	0.044 (3)	0.053 (3)	−0.018 (4)	−0.019 (3)	−0.0017 (16)

Geometric parameters (Å, º)

O1A—C4A	1.3753 (13)	C4'A—C5'A	1.3918 (15)
O1A—H1A	0.83 (3)	C5'A—C6'A	1.3902 (13)
C1A—C2A	1.399 (2)	C5'A—H5'A	0.9500
C1A—C6A	1.4013 (16)	C6'A—H6'A	0.9500
C1A—C7A	1.4938 (13)	C7'A—C8'A	1.5159 (12)
C2A—C3A	1.3935 (14)	C8'A—C9'A	1.5288 (14)
C2A—H2A	0.9500	C8'A—H83A	0.9900
C3A—C4A	1.3863 (19)	C8'A—H84A	0.9900
C3A—H3A	0.9500	C9'A—H94A	0.9800
C4A—C5A	1.3986 (18)	C9'A—H95A	0.9800
C5A—C6A	1.3908 (14)	C9'A—H96A	0.9800
C5A—H5A	0.9500	O11B—C11B	1.421 (3)
C6A—H6A	0.9500	O11B—H11B	0.8501
C7A—C7'A	1.350 (3)	C11B—H12B	0.9800
C7A—C8A	1.508 (3)	C11B—H13B	0.9800
O12A—C42A	1.3754 (15)	C11B—H14B	0.9800
C12A—C22A	1.399 (2)	O12B—C12B	1.421 (3)
C12A—C62A	1.4014 (18)	O12B—H11B	1.0714
C12A—C72A	1.4937 (15)	C12B—H11B	1.2507
C22A—C32A	1.3937 (16)	C12B—H15B	0.9800
C22A—H22A	0.9500	C12B—H16B	0.9800
C32A—C42A	1.386 (2)	C12B—H17B	0.9800
C32A—H32A	0.9500	O13B—C13B	1.420 (3)
C42A—C52A	1.399 (2)	C13B—H18B	0.9800
C52A—C62A	1.3909 (16)	C13B—H19B	0.9800
C52A—H52A	0.9500	C13B—H20B	0.9800
C62A—H62A	0.9500	O11C—O15C	0.66 (5)
C72A—C7'A	1.37 (4)	O11C—O13C	0.93 (3)
C72A—C8A	1.64 (4)	O11C—O12C	0.99 (3)
C8A—C9A	1.5266 (14)	O11C—H11C	0.8496
C8A—H81A	0.9900	O11C—H12C	0.8505
C8A—H82A	0.9900	O12C—O13C	1.31 (3)
C9A—H91A	0.9800	O12C—O14C	1.439 (19)
C9A—H92A	0.9800	O12C—O15C	1.61 (4)
C9A—H93A	0.9800	O12C—O12C^i	1.692 (14)
O1'A—C4'A	1.3753 (11)	O12C—H11C	1.2346
O1'A—H1'A	0.87 (2)	O12C—H12C	0.4986
C1'A—C2'A	1.3978 (12)	O13C—O14C	1.06 (3)
C1'A—C6'A	1.3987 (12)	O13C—O15C	1.31 (5)
C1'A—C7'A	1.4943 (11)	O13C—H11C	1.3417
C2'A—C3'A	1.3931 (12)	O14C—H11C	0.8353
C2'A—H2'A	0.9500	O14C—H12C	1.3006
C3'A—C4'A	1.3865 (14)	O15C—H11C	0.9059
C3'A—H3'A	0.9500	O15C—H12C	1.4085
C4A—O1A—H1A	105.8 (18)	C9'A—C8'A—H83A	109.1
C2A—C1A—C6A	117.59 (10)	C7'A—C8'A—H84A	109.1
C2A—C1A—C7A	122.03 (10)	C9'A—C8'A—H84A	109.1
C6A—C1A—C7A	120.33 (14)	H83A—C8'A—H84A	107.8
C3A—C2A—C1A	121.44 (10)	C8'A—C9'A—H94A	109.5
C3A—C2A—H2A	119.3	C8'A—C9'A—H95A	109.5
C1A—C2A—H2A	119.3	H94A—C9'A—H95A	109.5
C4A—C3A—C2A	119.77 (11)	C8'A—C9'A—H96A	109.5
C4A—C3A—H3A	120.1	H94A—C9'A—H96A	109.5
C2A—C3A—H3A	120.1	H95A—C9'A—H96A	109.5
O1A—C4A—C3A	117.69 (12)	C11B—O11B—H11B	111.4
O1A—C4A—C5A	122.12 (11)	C12B—O12B—H11B	58.3
C3A—C4A—C5A	120.17 (10)	O12B—C12B—H11B	46.8
C6A—C5A—C4A	119.30 (10)	O12B—C12B—H15B	109.5
C6A—C5A—H5A	120.4	H11B—C12B—H15B	123.1
C4A—C5A—H5A	120.4	O12B—C12B—H16B	109.5
C5A—C6A—C1A	121.71 (12)	H11B—C12B—H16B	62.8
C5A—C6A—H6A	119.1	H15B—C12B—H16B	109.5
C1A—C6A—H6A	119.1	O12B—C12B—H17B	109.5
C7'A—C7A—C1A	122.43 (19)	H11B—C12B—H17B	126.7
C7'A—C7A—C8A	123.99 (8)	H15B—C12B—H17B	109.5
C1A—C7A—C8A	113.55 (17)	H16B—C12B—H17B	109.5
C22A—C12A—C62A	117.61 (12)	O13B—C13B—H18B	109.5
C22A—C12A—C72A	122.05 (13)	O13B—C13B—H19B	109.5
C62A—C12A—C72A	120.33 (16)	H18B—C13B—H19B	109.5
C32A—C22A—C12A	121.43 (13)	O13B—C13B—H20B	109.5
C32A—C22A—H22A	119.3	H18B—C13B—H20B	109.5
C12A—C22A—H22A	119.3	H19B—C13B—H20B	109.5
C42A—C32A—C22A	119.76 (13)	O15C—O11C—O13C	109 (4)
C42A—C32A—H32A	120.1	O15C—O11C—O12C	153 (2)
C22A—C32A—H32A	120.1	O13C—O11C—O12C	86 (2)
O12A—C42A—C32A	117.72 (14)	O15C—O11C—H11C	72.5
O12A—C42A—C52A	122.09 (14)	O13C—O11C—H11C	97.4
C32A—C42A—C52A	120.19 (12)	O12C—O11C—H11C	84.1
C62A—C52A—C42A	119.27 (13)	O15C—O11C—H12C	137.2
C62A—C52A—H52A	120.4	O13C—O11C—H12C	112.7
C42A—C52A—H52A	120.4	O12C—O11C—H12C	30.3
C52A—C62A—C12A	121.70 (14)	H11C—O11C—H12C	94.2
C52A—C62A—H62A	119.2	O11C—O12C—O13C	45.4 (11)
C12A—C62A—H62A	119.2	O11C—O12C—O14C	8.1 (8)
C7'A—C72A—C12A	126 (3)	O13C—O12C—O14C	45.1 (13)
C7'A—C72A—C8A	113.8 (6)	O11C—O12C—O15C	10.6 (11)
C12A—C72A—C8A	120 (3)	O13C—O12C—O15C	52.2 (16)
C7A—C8A—C9A	112.79 (11)	O14C—O12C—O15C	7.1 (11)
C7A—C8A—C72A	3.6 (11)	O11C—O12C—O12C^i	113.7 (8)
C9A—C8A—C72A	109.9 (12)	O13C—O12C—O12C^i	150.5 (14)
C7A—C8A—H81A	109.0	O14C—O12C—O12C^i	117.8 (8)
C9A—C8A—H81A	109.0	O15C—O12C—O12C^i	111.4 (13)
C72A—C8A—H81A	112.4	O11C—O12C—H11C	43.2
C7A—C8A—H82A	109.0	O13C—O12C—H11C	63.6
C9A—C8A—H82A	109.0	O14C—O12C—H11C	35.4
C72A—C8A—H82A	108.6	O15C—O12C—H11C	34.2
H81A—C8A—H82A	107.8	O12C^i—O12C—H11C	119.0
C8A—C9A—H91A	109.5	O11C—O12C—H12C	59.5
C8A—C9A—H92A	109.5	O13C—O12C—H12C	101.1
H91A—C9A—H92A	109.5	O14C—O12C—H12C	64.1
C8A—C9A—H93A	109.5	O15C—O12C—H12C	58.3
H91A—C9A—H93A	109.5	O12C^i—O12C—H12C	54.3
H92A—C9A—H93A	109.5	H11C—O12C—H12C	79.6
C4'A—O1'A—H1'A	108.3 (15)	O11C—O13C—O14C	27.0 (13)
C2'A—C1'A—C6'A	117.49 (8)	O11C—O13C—O12C	49 (2)
C2'A—C1'A—C7'A	122.24 (7)	O14C—O13C—O12C	74 (2)
C6'A—C1'A—C7'A	120.23 (7)	O11C—O13C—O15C	28.4 (19)
C3'A—C2'A—C1'A	121.56 (8)	O14C—O13C—O15C	1.8 (14)
C3'A—C2'A—H2'A	119.2	O12C—O13C—O15C	75.6 (18)
C1'A—C2'A—H2'A	119.2	O11C—O13C—H11C	38.9
C4'A—C3'A—C2'A	119.75 (9)	O14C—O13C—H11C	38.5
C4'A—C3'A—H3'A	120.1	O12C—O13C—H11C	55.5
C2'A—C3'A—H3'A	120.1	O15C—O13C—H11C	39.9
O1'A—C4'A—C3'A	118.02 (9)	O13C—O14C—O12C	60.9 (17)
O1'A—C4'A—C5'A	122.10 (9)	O13C—O14C—H11C	89.2
C3'A—C4'A—C5'A	119.89 (8)	O12C—O14C—H11C	58.8
C6'A—C5'A—C4'A	119.78 (8)	O13C—O14C—H12C	77.3
C6'A—C5'A—H5'A	120.1	O12C—O14C—H12C	20.2
C4'A—C5'A—H5'A	120.1	H11C—O14C—H12C	67.3
C5'A—C6'A—C1'A	121.52 (8)	O11C—O15C—O13C	42 (3)
C5'A—C6'A—H6'A	119.2	O11C—O15C—O12C	16.0 (11)
C1'A—C6'A—H6'A	119.2	O13C—O15C—O12C	52 (2)
C7A—C7'A—C72A	7.0 (10)	O11C—O15C—H11C	63.4
C7A—C7'A—C1'A	122.26 (9)	O13C—O15C—H11C	71.9
C72A—C7'A—C1'A	129.0 (13)	O12C—O15C—H11C	49.9
C7A—C7'A—C8'A	124.51 (10)	O11C—O15C—H12C	24.2
C72A—C7'A—C8'A	117.8 (13)	O13C—O15C—H12C	66.2
C1'A—C7'A—C8'A	113.21 (7)	O12C—O15C—H12C	17.5
C7'A—C8'A—C9'A	112.55 (7)	H11C—O15C—H12C	60.6
C7'A—C8'A—H83A	109.1
C6A—C1A—C2A—C3A	−1.56 (19)	C12A—C72A—C7'A—C7A	−171 (15)
C7A—C1A—C2A—C3A	−178.81 (19)	C8A—C72A—C7'A—C7A	12 (11)
C1A—C2A—C3A—C4A	0.9 (2)	C12A—C72A—C7'A—C1'A	171.2 (15)
C2A—C3A—C4A—O1A	178.96 (12)	C8A—C72A—C7'A—C1'A	−6 (3)
C2A—C3A—C4A—C5A	0.39 (19)	C12A—C72A—C7'A—C8'A	−8 (3)
O1A—C4A—C5A—C6A	−179.54 (11)	C8A—C72A—C7'A—C8'A	175.0 (11)
C3A—C4A—C5A—C6A	−1.04 (18)	C2'A—C1'A—C7'A—C7A	−63.33 (15)
C4A—C5A—C6A—C1A	0.39 (17)	C6'A—C1'A—C7'A—C7A	119.19 (13)
C2A—C1A—C6A—C5A	0.89 (18)	C2'A—C1'A—C7'A—C72A	−60.8 (15)
C7A—C1A—C6A—C5A	178.19 (17)	C6'A—C1'A—C7'A—C72A	121.7 (15)
C2A—C1A—C7A—C7'A	−57.9 (3)	C2'A—C1'A—C7'A—C8'A	118.09 (9)
C6A—C1A—C7A—C7'A	124.88 (14)	C6'A—C1'A—C7'A—C8'A	−59.39 (10)
C2A—C1A—C7A—C8A	123.85 (13)	C7A—C7'A—C8'A—C9'A	114.73 (13)
C6A—C1A—C7A—C8A	−53.3 (2)	C72A—C7'A—C8'A—C9'A	112.3 (13)
C62A—C12A—C22A—C32A	0 (3)	C1'A—C7'A—C8'A—C9'A	−66.72 (9)
C72A—C12A—C22A—C32A	179 (3)	O15C—O11C—O12C—O13C	−126 (6)
C12A—C22A—C32A—C42A	0 (2)	O15C—O11C—O12C—O14C	−42 (7)
C22A—C32A—C42A—O12A	−178.5 (13)	O13C—O11C—O12C—O14C	84 (5)
C22A—C32A—C42A—C52A	1.5 (19)	O13C—O11C—O12C—O15C	126 (6)
O12A—C42A—C52A—C62A	177.5 (13)	O15C—O11C—O12C—O12C^i	79 (6)
C32A—C42A—C52A—C62A	−2.5 (18)	O13C—O11C—O12C—O12C^i	−154.3 (18)
C42A—C52A—C62A—C12A	2 (2)	O15C—O11C—O13C—O14C	2 (2)
C22A—C12A—C62A—C52A	−1 (3)	O12C—O11C—O13C—O14C	−155 (2)
C72A—C12A—C62A—C52A	180 (3)	O15C—O11C—O13C—O12C	158 (2)
C22A—C12A—C72A—C7'A	−56 (4)	O12C—O11C—O13C—O15C	−158 (2)
C62A—C12A—C72A—C7'A	123 (2)	O14C—O12C—O13C—O11C	−11.4 (12)
C22A—C12A—C72A—C8A	120.8 (17)	O15C—O12C—O13C—O11C	−10.8 (14)
C62A—C12A—C72A—C8A	−60 (3)	O12C^i—O12C—O13C—O11C	54 (3)
C7'A—C7A—C8A—C9A	118.87 (18)	O11C—O12C—O13C—O14C	11.4 (12)
C1A—C7A—C8A—C9A	−62.96 (16)	O15C—O12C—O13C—O14C	0.6 (12)
C7'A—C7A—C8A—C72A	157 (13)	O12C^i—O12C—O13C—O14C	65 (3)
C1A—C7A—C8A—C72A	−25 (13)	O11C—O12C—O13C—O15C	10.8 (14)
C7'A—C72A—C8A—C7A	−21 (11)	O14C—O12C—O13C—O15C	−0.6 (12)
C12A—C72A—C8A—C7A	162 (14)	O12C^i—O12C—O13C—O15C	64 (3)
C7'A—C72A—C8A—C9A	122.3 (18)	O11C—O13C—O14C—O12C	19.1 (15)
C12A—C72A—C8A—C9A	−55.2 (18)	O15C—O13C—O14C—O12C	162 (42)
C6'A—C1'A—C2'A—C3'A	−0.34 (14)	O11C—O12C—O14C—O13C	−88 (5)
C7'A—C1'A—C2'A—C3'A	−177.89 (9)	O15C—O12C—O14C—O13C	−176 (8)
C1'A—C2'A—C3'A—C4'A	0.16 (16)	O12C^i—O12C—O14C—O13C	−149.7 (17)
C2'A—C3'A—C4'A—O1'A	179.18 (10)	O12C—O11C—O15C—O13C	122 (6)
C2'A—C3'A—C4'A—C5'A	−0.34 (17)	O13C—O11C—O15C—O12C	−122 (6)
O1'A—C4'A—C5'A—C6'A	−178.78 (10)	O14C—O13C—O15C—O11C	−36 (41)
C3'A—C4'A—C5'A—C6'A	0.72 (17)	O12C—O13C—O15C—O11C	−17.3 (15)
C4'A—C5'A—C6'A—C1'A	−0.93 (16)	O11C—O13C—O15C—O12C	17.3 (15)
C2'A—C1'A—C6'A—C5'A	0.73 (14)	O14C—O13C—O15C—O12C	−18 (42)
C7'A—C1'A—C6'A—C5'A	178.33 (9)	O13C—O12C—O15C—O11C	47 (6)
C1A—C7A—C7'A—C72A	16 (12)	O14C—O12C—O15C—O11C	50 (7)
C8A—C7A—C7'A—C72A	−166 (13)	O12C^i—O12C—O15C—O11C	−105 (6)
C1A—C7A—C7'A—C1'A	179.76 (12)	O11C—O12C—O15C—O13C	−47 (6)
C8A—C7A—C7'A—C1'A	−2.2 (2)	O14C—O12C—O15C—O13C	3 (7)
C1A—C7A—C7'A—C8'A	−1.8 (2)	O12C^i—O12C—O15C—O13C	−151.5 (16)
C8A—C7A—C7'A—C8'A	176.19 (12)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O1′A^ii	0.83 (3)	1.95 (3)	2.7760 (18)	170 (3)
O1′A—H1′A···O11B^iii	0.87 (2)	1.82 (2)	2.683 (3)	170 (2)
O11B—H11B···O11C^iv	0.85	1.83	2.677 (12)	179
O11C—H11C···O1A^v	0.85	2.20	3.055 (10)	179

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