11,20-Dihy­droxy-3-oxopregna-1,4-dien-21-oic acid monohydrate

Guo, Z.; Tang, S.; Duan, H.

doi:10.1107/S1600536811015224

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1290

doi:10.1107/S1600536811015224

Open

access

11,20-Dihydroxy-3-oxopregna-1,4-dien-21-oic acid monohydrate

Zhanqiang Guo,^a Shengan Tang ^a and Hongquan Duan ^a ^*

^aSchool of Pharmaceutical Sciences, Research Center of Basic Medical Sciences, Tianjin Medical University, Tianjin 300070, People's Republic of China
^*Correspondence e-mail: duanhp@tijmu.edu.cn

(Received 26 January 2011; accepted 22 April 2011; online 7 May 2011)

The title compound, C₂₁H₂₈O₅·H₂O, is the hydrate of a steroid derivative and was obtained by degradation of solid prednisolone sodium phosphate. The six C atoms in ring A are nearly co-planar with a mean deviation of 0.015 Å. Rings B and C are both in chair conformations, while ring D has an envelope form. In the crystal, intermolecular O—H⋯O hydrogen-bonding interactions occur between the hydroxy groups, carbonyl O atoms and solvent water molecules, resulting in an overall three-dimensional structure.

Related literature

For general background to substances related to prednisolone sodium phosphate, see: Dekker (1980 ); Stroud et al. (1980 ); Mason (1938 ); Edmonds et al. (2006 ); Gazdag et al. (1998 ). For related structures, see: Suitschmezian et al. (2008 ); Rachwal et al. (1996 ).

Experimental

Crystal data

C₂₁H₂₈O₅·H₂O
M_r = 378.45
Orthorhombic, P 2₁ 2₁ 2₁
a = 11.801 (2) Å
b = 12.526 (3) Å
c = 12.884 (3) Å
V = 1904.5 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 113 K
0.20 × 0.10 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: ψ scan (CrystalClear; Rigaku, 2005 ) T_min = 0.981, T_max = 0.991
13023 measured reflections
1922 independent reflections
1809 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.085
S = 1.06
1922 reflections
232 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.82	1.92	2.708 (2)	161
O3—H3⋯O2ⁱⁱ	0.82	2.06	2.819 (2)	153
O4—H4⋯O6ⁱⁱⁱ	0.82	1.84	2.646 (2)	167
O6—H61⋯O1	0.86	1.92	2.765 (2)	165
O6—H62⋯O5^iv	0.86	2.10	2.938 (2)	166
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y, z-{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y, z-1; (iv) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811015224/bh2337sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811015224/bh2337Isup2.hkl

checkCIF report

Comment top

In the molecule of the title compound, (Fig. 1), all bond lengths and angles are within normal ranges (Mason, 1938; Edmonds et al., 2006; Gazdag et al., 1998; Rachwal et al., 1996). Six carbon atoms in ring A (C1···C5/C10) are nearly in the same plane with the average atomic displacement of 0.015 Å. Rings B (C5···C10) and C (C8/C9/C11···C14) are both in chair conformations. Ring D (C13···C17) has an envelope form with C13 as the out-of-plane atom. Through extensive O—H···O hydrogen bonds between the main molecule and lattice water molecule, a three dimensional supramolecular network is formed. The water molecules are involved in O—H···O hydrogen bonding with atoms O1, O5 and O4 belonging to hydroxy groups, and intermolecular O—H···O hydrogen-bonding interactions are formed between hydroxy groups and carbonyl O atom, resulting in an overall three-dimensional crystal structure (Fig. 2).

Related literature top

For general background to substances related to prednisolone sodium phosphate, see: Dekker (1980); Stroud et al. (1980); Mason (1938); Edmonds et al. (2006); Gazdag et al. (1998). For related structures, see: Suitschmezian et al. (2008); Rachwal et al. (1996).

Experimental top

The title compound (Dekker, 1980; Stroud et al., 1980) was obtained by degradation of solid prednisolone sodium phosphate at 373 K for 72 h, then extracted and isolated using HSCCC followed by preparative HPLC. Finally, the crystals were prepared by slow evaporation of the solvent from a saturated solution in methanol/acetone/H₂O at room temperature (Suitschmezian et al., 2008).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids, and H atoms are shown as small spheres of arbitrary radius.
	Fig. 2. The packing of (I), showing the three-dimensional structure, with intermolecular hydrogen bonds (dashed lines); for clarity H atoms have been omitted.

11,20-Dihydroxy-3-oxopregna-1,4-dien-21-oic acid monohydrate top

Crystal data top

C₂₁H₂₈O₅·H₂O	F(000) = 816
M_r = 378.45	D_x = 1.320 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 11.801 (2) Å	θ = 4.1–22.5°
b = 12.526 (3) Å	µ = 0.10 mm⁻¹
c = 12.884 (3) Å	T = 113 K
V = 1904.5 (7) Å³	Block, colourless
Z = 4	0.20 × 0.10 × 0.10 mm

Data collection top

Rigaku Saturn CCD area=detector diffractometer	1922 independent reflections
Radiation source: rotating anode	1809 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.046
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.0°, θ_min = 2.3°
ω and ϕ scans	h = −12→14
Absorption correction: ψ scan (CrystalClear; Rigaku, 2005)	k = −14→11
T_min = 0.981, T_max = 0.991	l = −15→15
13023 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.085	w = 1/[σ²(F_o²) + (0.0589P)² + 0.0073P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
1922 reflections	Δρ_max = 0.22 e Å⁻³
232 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 constraints	Extinction coefficient: 0.026 (3)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₂₁H₂₈O₅·H₂O	V = 1904.5 (7) Å³
M_r = 378.45	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 11.801 (2) Å	µ = 0.10 mm⁻¹
b = 12.526 (3) Å	T = 113 K
c = 12.884 (3) Å	0.20 × 0.10 × 0.10 mm

Data collection top

Rigaku Saturn CCD area=detector diffractometer	1922 independent reflections
Absorption correction: ψ scan (CrystalClear; Rigaku, 2005)	1809 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.991	R_int = 0.046
13023 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 1.06	Δρ_max = 0.22 e Å⁻³
1922 reflections	Δρ_min = −0.18 e Å⁻³
232 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.30262 (15)	0.07528 (11)	0.89120 (11)	0.0247 (4)
O2	0.06804 (6)	0.10188 (5)	0.41310 (5)	0.0210 (4)
H2	0.0958	0.0443	0.3967	0.031*
O3	0.15678 (6)	0.53818 (5)	0.12731 (5)	0.0257 (4)
H3	0.1016	0.5765	0.1169	0.039*
O4	0.29729 (6)	0.36129 (5)	0.13021 (5)	0.0287 (4)
H4	0.3291	0.3118	0.1004	0.043*
O5	0.14172 (6)	0.27905 (5)	0.07258 (5)	0.0340 (4)
O6	0.41158 (6)	0.22413 (5)	1.01436 (5)	0.0318 (5)
H61	0.3671	0.1799	0.9832	0.048*
H62	0.4755	0.2338	0.9842	0.048*
C1	0.17278 (6)	0.04907 (5)	0.64360 (5)	0.0194 (5)
H1A	0.1791	0.0060	0.5851	0.023*
C2	0.2366 (2)	0.02545 (16)	0.72564 (16)	0.0199 (5)
H2A	0.2822	−0.0351	0.7241	0.024*
C3	0.2363 (2)	0.09259 (17)	0.81752 (17)	0.0207 (5)
C4	0.1569 (2)	0.18171 (17)	0.82009 (17)	0.0224 (5)
H4A	0.1530	0.2240	0.8793	0.027*
C5	0.0899 (2)	0.20402 (17)	0.73978 (16)	0.0201 (5)
C6	0.0106 (2)	0.29859 (16)	0.74117 (17)	0.0241 (5)
H6A	0.0172	0.3356	0.8070	0.029*
H6B	−0.0670	0.2740	0.7340	0.029*
C7	0.0390 (2)	0.37501 (17)	0.65283 (16)	0.0228 (5)
H7A	0.1116	0.4084	0.6669	0.027*
H7B	−0.0178	0.4309	0.6503	0.027*
C8	0.0444 (2)	0.31972 (16)	0.54711 (16)	0.0181 (5)
H8A	−0.0314	0.2940	0.5284	0.022*
C9	0.12720 (19)	0.22354 (16)	0.55283 (15)	0.0167 (5)
H9A	0.1988	0.2540	0.5775	0.020*
C10	0.09127 (19)	0.14101 (16)	0.63966 (16)	0.0184 (5)
C11	0.15618 (19)	0.17277 (15)	0.44709 (16)	0.0174 (5)
H11A	0.2245	0.1295	0.4572	0.021*
C12	0.18324 (19)	0.25475 (16)	0.36265 (16)	0.0181 (5)
H12A	0.1871	0.2185	0.2962	0.022*
H12B	0.2573	0.2853	0.3764	0.022*
C13	0.09600 (19)	0.34550 (16)	0.35520 (16)	0.0168 (5)
C14	0.0867 (2)	0.39593 (16)	0.46352 (16)	0.0184 (5)
H14A	0.1635	0.4173	0.4837	0.022*
C15	0.0199 (2)	0.49927 (16)	0.44477 (17)	0.0227 (5)
H15A	0.0346	0.5513	0.4989	0.027*
H15B	−0.0609	0.4854	0.4416	0.027*
C16	0.0655 (2)	0.53830 (17)	0.33857 (17)	0.0229 (5)
H16A	0.1135	0.6004	0.3478	0.027*
H16B	0.0032	0.5574	0.2930	0.027*
C17	0.1345 (2)	0.44450 (16)	0.29164 (16)	0.0195 (5)
H17A	0.2148	0.4572	0.3068	0.023*
C18	−0.0186 (2)	0.30495 (17)	0.31488 (17)	0.0200 (5)
H18A	−0.0077	0.2683	0.2502	0.030*
H18B	−0.0687	0.3644	0.3046	0.030*
H18C	−0.0511	0.2568	0.3647	0.030*
C19	−0.0274 (2)	0.08996 (18)	0.62344 (17)	0.0235 (5)
H19A	−0.0211	0.0305	0.5768	0.035*
H19B	−0.0780	0.1421	0.5946	0.035*
H19C	−0.0564	0.0657	0.6889	0.035*
C20	0.1205 (2)	0.43974 (17)	0.17282 (16)	0.0215 (5)
H20A	0.0400	0.4298	0.1570	0.026*
C21	0.1867 (2)	0.35143 (18)	0.12036 (17)	0.0233 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0291 (10)	0.0234 (8)	0.0217 (8)	0.0045 (7)	−0.0075 (7)	0.0019 (6)
O2	0.0207 (9)	0.0169 (8)	0.0253 (8)	−0.0009 (6)	0.0002 (7)	−0.0033 (7)
O3	0.0265 (10)	0.0221 (8)	0.0284 (9)	0.0012 (7)	0.0011 (7)	0.0086 (7)
O4	0.0228 (10)	0.0311 (9)	0.0322 (9)	0.0030 (7)	0.0013 (8)	−0.0065 (7)
O5	0.0325 (11)	0.0357 (9)	0.0337 (9)	−0.0032 (8)	0.0029 (9)	−0.0137 (8)
O6	0.0277 (11)	0.0355 (10)	0.0323 (9)	0.0005 (8)	0.0001 (8)	−0.0097 (8)
C1	0.0205 (13)	0.0162 (10)	0.0214 (11)	0.0000 (9)	0.0029 (10)	0.0009 (9)
C2	0.0215 (13)	0.0138 (10)	0.0246 (11)	0.0029 (9)	−0.0001 (10)	0.0040 (9)
C3	0.0233 (13)	0.0181 (11)	0.0207 (11)	−0.0007 (9)	0.0016 (10)	0.0040 (9)
C4	0.0266 (14)	0.0222 (11)	0.0184 (11)	0.0017 (10)	0.0032 (10)	0.0001 (9)
C5	0.0213 (13)	0.0206 (11)	0.0184 (11)	0.0007 (9)	0.0022 (10)	0.0021 (9)
C6	0.0282 (14)	0.0233 (11)	0.0207 (11)	0.0111 (10)	0.0036 (10)	−0.0003 (9)
C7	0.0277 (14)	0.0209 (11)	0.0197 (11)	0.0069 (9)	0.0001 (10)	0.0000 (9)
C8	0.0180 (13)	0.0177 (11)	0.0187 (11)	0.0035 (9)	−0.0004 (9)	−0.0006 (9)
C9	0.0155 (12)	0.0173 (10)	0.0174 (11)	0.0011 (9)	0.0009 (9)	0.0009 (9)
C10	0.0188 (13)	0.0180 (10)	0.0184 (11)	0.0023 (9)	−0.0005 (10)	0.0041 (9)
C11	0.0151 (12)	0.0160 (10)	0.0209 (11)	0.0017 (9)	−0.0015 (9)	−0.0020 (9)
C12	0.0176 (13)	0.0186 (10)	0.0181 (11)	0.0013 (9)	0.0010 (10)	−0.0023 (8)
C13	0.0160 (12)	0.0168 (10)	0.0176 (11)	0.0006 (9)	0.0004 (9)	−0.0003 (9)
C14	0.0190 (12)	0.0172 (10)	0.0189 (11)	0.0006 (9)	−0.0028 (9)	−0.0003 (9)
C15	0.0282 (14)	0.0173 (11)	0.0226 (11)	0.0041 (10)	−0.0008 (10)	−0.0001 (9)
C16	0.0290 (14)	0.0164 (10)	0.0232 (12)	0.0019 (10)	−0.0018 (10)	0.0021 (9)
C17	0.0206 (13)	0.0177 (11)	0.0201 (11)	−0.0021 (9)	−0.0018 (10)	0.0030 (9)
C18	0.0183 (13)	0.0194 (11)	0.0222 (11)	0.0019 (9)	−0.0017 (10)	0.0009 (9)
C19	0.0201 (13)	0.0250 (11)	0.0254 (12)	−0.0013 (10)	0.0005 (10)	0.0042 (10)
C20	0.0205 (13)	0.0226 (11)	0.0213 (12)	−0.0019 (9)	−0.0008 (10)	0.0027 (9)
C21	0.0243 (14)	0.0268 (12)	0.0189 (11)	−0.0011 (10)	0.0001 (10)	0.0040 (10)

Geometric parameters (Å, º) top

O1—C3	1.249 (3)	C9—C10	1.581 (3)
O2—C11	1.436 (2)	C9—H9A	0.9800
O2—H2	0.8200	C10—C19	1.554 (3)
O3—C20	1.431 (2)	C11—C12	1.530 (3)
O3—H3	0.8200	C11—H11A	0.9800
O4—C21	1.317 (3)	C12—C13	1.537 (3)
O4—H4	0.8200	C12—H12A	0.9700
O5—C21	1.218 (2)	C12—H12B	0.9700
O6—H61	0.8616	C13—C18	1.535 (3)
O6—H62	0.8572	C13—C14	1.536 (3)
C1—C2	1.331 (2)	C13—C17	1.554 (3)
C1—C10	1.501 (2)	C14—C15	1.535 (3)
C1—H1A	0.9300	C14—H14A	0.9800
C2—C3	1.452 (3)	C15—C16	1.550 (3)
C2—H2A	0.9300	C15—H15A	0.9700
C3—C4	1.458 (3)	C15—H15B	0.9700
C4—C5	1.332 (3)	C16—C17	1.552 (3)
C4—H4A	0.9300	C16—H16A	0.9700
C5—C6	1.510 (3)	C16—H16B	0.9700
C5—C10	1.512 (3)	C17—C20	1.541 (3)
C6—C7	1.525 (3)	C17—H17A	0.9800
C6—H6A	0.9700	C18—H18A	0.9600
C6—H6B	0.9700	C18—H18B	0.9600
C7—C8	1.529 (3)	C18—H18C	0.9600
C7—H7A	0.9700	C19—H19A	0.9600
C7—H7B	0.9700	C19—H19B	0.9600
C8—C14	1.524 (3)	C19—H19C	0.9600
C8—C9	1.553 (3)	C20—C21	1.514 (3)
C8—H8A	0.9800	C20—H20A	0.9800
C9—C11	1.542 (3)

C11—O2—H2	109.5	C11—C12—H12A	108.8
C20—O3—H3	109.5	C13—C12—H12A	108.8
C21—O4—H4	109.7	C11—C12—H12B	108.8
H61—O6—H62	114.6	C13—C12—H12B	108.8
C2—C1—C10	124.04 (13)	H12A—C12—H12B	107.7
C2—C1—H1A	118.0	C18—C13—C14	112.39 (19)
C10—C1—H1A	118.0	C18—C13—C12	111.51 (17)
C1—C2—C3	121.15 (17)	C14—C13—C12	107.16 (17)
C1—C2—H2A	119.4	C18—C13—C17	110.08 (18)
C3—C2—H2A	119.4	C14—C13—C17	99.87 (15)
O1—C3—C2	121.2 (2)	C12—C13—C17	115.30 (18)
O1—C3—C4	121.2 (2)	C8—C14—C15	118.08 (19)
C2—C3—C4	117.6 (2)	C8—C14—C13	114.08 (16)
C5—C4—C3	121.6 (2)	C15—C14—C13	103.91 (17)
C5—C4—H4A	119.2	C8—C14—H14A	106.7
C3—C4—H4A	119.2	C15—C14—H14A	106.7
C4—C5—C6	121.6 (2)	C13—C14—H14A	106.7
C4—C5—C10	123.2 (2)	C14—C15—C16	103.08 (18)
C6—C5—C10	115.21 (18)	C14—C15—H15A	111.1
C5—C6—C7	110.30 (19)	C16—C15—H15A	111.1
C5—C6—H6A	109.6	C14—C15—H15B	111.1
C7—C6—H6A	109.6	C16—C15—H15B	111.1
C5—C6—H6B	109.6	H15A—C15—H15B	109.1
C7—C6—H6B	109.6	C15—C16—C17	106.71 (17)
H6A—C6—H6B	108.1	C15—C16—H16A	110.4
C6—C7—C8	112.93 (17)	C17—C16—H16A	110.4
C6—C7—H7A	109.0	C15—C16—H16B	110.4
C8—C7—H7A	109.0	C17—C16—H16B	110.4
C6—C7—H7B	109.0	H16A—C16—H16B	108.6
C8—C7—H7B	109.0	C20—C17—C16	111.11 (18)
H7A—C7—H7B	107.8	C20—C17—C13	117.47 (18)
C14—C8—C7	111.05 (17)	C16—C17—C13	104.20 (16)
C14—C8—C9	108.23 (18)	C20—C17—H17A	107.9
C7—C8—C9	109.56 (17)	C16—C17—H17A	107.9
C14—C8—H8A	109.3	C13—C17—H17A	107.9
C7—C8—H8A	109.3	C13—C18—H18A	109.5
C9—C8—H8A	109.3	C13—C18—H18B	109.5
C11—C9—C8	114.68 (17)	H18A—C18—H18B	109.5
C11—C9—C10	114.52 (16)	C13—C18—H18C	109.5
C8—C9—C10	111.82 (17)	H18A—C18—H18C	109.5
C11—C9—H9A	104.8	H18B—C18—H18C	109.5
C8—C9—H9A	104.8	C10—C19—H19A	109.5
C10—C9—H9A	104.8	C10—C19—H19B	109.5
C1—C10—C5	112.22 (16)	H19A—C19—H19B	109.5
C1—C10—C19	105.45 (15)	C10—C19—H19C	109.5
C5—C10—C19	108.68 (18)	H19A—C19—H19C	109.5
C1—C10—C9	110.70 (16)	H19B—C19—H19C	109.5
C5—C10—C9	105.37 (16)	O3—C20—C21	107.00 (16)
C19—C10—C9	114.56 (18)	O3—C20—C17	109.98 (17)
O2—C11—C12	110.45 (16)	C21—C20—C17	114.63 (19)
O2—C11—C9	111.34 (16)	O3—C20—H20A	108.4
C12—C11—C9	113.44 (16)	C21—C20—H20A	108.4
O2—C11—H11A	107.1	C17—C20—H20A	108.4
C12—C11—H11A	107.1	O5—C21—O4	123.4 (2)
C9—C11—H11A	107.1	O5—C21—C20	123.0 (2)
C11—C12—C13	113.65 (17)	O4—C21—C20	113.57 (18)

C10—C1—C2—C3	−3.6 (3)	O2—C11—C12—C13	77.4 (2)
C1—C2—C3—O1	−174.30 (19)	C9—C11—C12—C13	−48.4 (3)
C1—C2—C3—C4	4.9 (3)	C11—C12—C13—C18	−68.5 (2)
O1—C3—C4—C5	176.5 (2)	C11—C12—C13—C14	54.9 (2)
C2—C3—C4—C5	−2.7 (3)	C11—C12—C13—C17	165.03 (17)
C3—C4—C5—C6	−177.9 (2)	C7—C8—C14—C15	−58.4 (3)
C3—C4—C5—C10	−0.9 (4)	C9—C8—C14—C15	−178.66 (18)
C4—C5—C6—C7	120.0 (2)	C7—C8—C14—C13	179.2 (2)
C10—C5—C6—C7	−57.2 (3)	C9—C8—C14—C13	58.9 (2)
C5—C6—C7—C8	52.4 (3)	C18—C13—C14—C8	60.7 (2)
C6—C7—C8—C14	−173.2 (2)	C12—C13—C14—C8	−62.1 (2)
C6—C7—C8—C9	−53.7 (3)	C17—C13—C14—C8	177.38 (19)
C14—C8—C9—C11	−48.7 (2)	C18—C13—C14—C15	−69.2 (2)
C7—C8—C9—C11	−169.93 (19)	C12—C13—C14—C15	167.97 (17)
C14—C8—C9—C10	178.76 (17)	C17—C13—C14—C15	47.5 (2)
C7—C8—C9—C10	57.5 (2)	C8—C14—C15—C16	−164.81 (19)
C2—C1—C10—C5	0.1 (2)	C13—C14—C15—C16	−37.3 (2)
C2—C1—C10—C19	−118.10 (18)	C14—C15—C16—C17	12.2 (2)
C2—C1—C10—C9	117.47 (18)	C15—C16—C17—C20	144.16 (19)
C4—C5—C10—C1	2.2 (3)	C15—C16—C17—C13	16.7 (2)
C6—C5—C10—C1	179.43 (17)	C18—C13—C17—C20	−43.8 (3)
C4—C5—C10—C19	118.5 (2)	C14—C13—C17—C20	−162.2 (2)
C6—C5—C10—C19	−64.4 (2)	C12—C13—C17—C20	83.4 (3)
C4—C5—C10—C9	−118.3 (2)	C18—C13—C17—C16	79.6 (2)
C6—C5—C10—C9	58.9 (2)	C14—C13—C17—C16	−38.8 (2)
C11—C9—C10—C1	47.5 (2)	C12—C13—C17—C16	−153.20 (19)
C8—C9—C10—C1	−179.92 (15)	C16—C17—C20—O3	58.4 (2)
C11—C9—C10—C5	169.00 (19)	C13—C17—C20—O3	178.26 (17)
C8—C9—C10—C5	−58.4 (2)	C16—C17—C20—C21	179.04 (18)
C11—C9—C10—C19	−71.6 (2)	C13—C17—C20—C21	−61.2 (3)
C8—C9—C10—C19	61.0 (2)	O3—C20—C21—O5	−120.4 (2)
C8—C9—C11—O2	−80.3 (2)	C17—C20—C21—O5	117.4 (2)
C10—C9—C11—O2	51.0 (2)	O3—C20—C21—O4	58.8 (2)
C8—C9—C11—C12	45.0 (3)	C17—C20—C21—O4	−63.5 (2)
C10—C9—C11—C12	176.29 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	1.92	2.708 (2)	161
O3—H3···O2ⁱⁱ	0.82	2.06	2.819 (2)	153
O4—H4···O6ⁱⁱⁱ	0.82	1.84	2.646 (2)	167
O6—H61···O1	0.86	1.92	2.765 (2)	165
O6—H62···O5^iv	0.86	2.10	2.938 (2)	166

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₈O₅·H₂O
M_r	378.45
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	113
a, b, c (Å)	11.801 (2), 12.526 (3), 12.884 (3)
V (Å³)	1904.5 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Rigaku Saturn CCD area=detector diffractometer
Absorption correction	ψ scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.981, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	13023, 1922, 1809
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.085, 1.06
No. of reflections	1922
No. of parameters	232
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.18

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	1.92	2.708 (2)	161.0
O3—H3···O2ⁱⁱ	0.82	2.06	2.819 (2)	153.1
O4—H4···O6ⁱⁱⁱ	0.82	1.84	2.646 (2)	167.4
O6—H61···O1	0.86	1.92	2.765 (2)	164.8
O6—H62···O5^iv	0.86	2.10	2.938 (2)	165.7

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

Acknowledgements

The authors are very grateful to the Central Laboratory of Nankai University for the X-ray data collection. Special thanks go to Dr Xie Chengzhi (School of Pharmaceutical Sciences, Tianjin Medical University) for his invaluable support.

References

Dekker, D. (1980). Pharm. Weekbl. Sci. Ed. 2, 87–95. CrossRef CAS Google Scholar
Edmonds, J. S., Morita, M., Turner, P., Skelton, B. W. & White, A. H. (2006). Steroids, 71, 34–41. Web of Science CrossRef PubMed CAS Google Scholar
Gazdag, M., Babják, M., Brlik, J., Mahó, S., Tuba, Z. & Görög, S. (1998). J. Pharm. Biomed. Anal. 17, 1029–1036. Web of Science CrossRef CAS PubMed Google Scholar
Mason, H. J. (1938). J. Biol. Chem. 124, 475–479. CAS Google Scholar
Rachwal, S., Pop, E. & Brewster, M. E. (1996). Steroids, 61, 524–530. CrossRef CAS PubMed Web of Science Google Scholar
Rigaku (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stroud, N., Richardson, N. E., Davies, D. J. G. & Norton, D. A. (1980). Analyst, 105, 455–461. CrossRef CAS PubMed Web of Science Google Scholar
Suitschmezian, V., Jess, I., Sehnert, J., Seyfarth, L., Senker, J. & Näther, C. (2008). Cryst. Growth Des. 8, 98–107. Google Scholar