2-[Bis(3,5-dimethyl­phen­yl)­phosphor­yl]­propan-2-ol hemihydrate

Chu, Q.-Y.; Liu, S.; Liu, Y.-Y.; Chen, W.; Zhu, H.-J.

doi:10.1107/S1600536808016681

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1231

doi:10.1107/S1600536808016681

Open

access

2-[Bis(3,5-dimethylphenyl)phosphoryl]propan-2-ol hemihydrate

Qing-Yan Chu,^a Shan Liu,^a Yuan-Yuan Liu,^a Wei Chen ^a and Hong-Jun Zhu ^a ^*

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: zhuhj@njut.edu.cn

(Received 29 May 2008; accepted 31 May 2008; online 7 June 2008)

In the organic molecule of the title compound, C₁₉H₂₅O₂P·0.5H₂O, the benzene rings are oriented at a dihedral angle of 54.04 (3)°. Intramolecular C—H⋯O hydrogen bonds result in the formation of two five-membered planar rings, which are oriented with respect to the adjacent benzene rings at dihedral angles of 2.66 (3) and 2.79 (3)°. In the crystal structure, intermolecular O—H⋯O hydrogen bonds link the molecules. The water oxygen atom lies on a twofold rotation axis.

Related literature

For related literature, see: Takao & Kazuhiko (1997 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₉H₂₅O₂P·0.5H₂O
M_r = 324.87
Monoclinic, C 2/c
a = 30.129 (6) Å
b = 6.2830 (13) Å
c = 20.192 (4) Å
β = 106.76 (3)°
V = 3660.1 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 298 (2) K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.969, T_max = 0.984
6573 measured reflections
3298 independent reflections
1904 reflections with I > 2σ(I)
R_int = 0.049
3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.205
S = 1.03
3298 reflections
206 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
OW—HWA⋯O2ⁱ	0.85	2.24	2.811 (3)	124
O1—H1A⋯O2ⁱⁱ	0.82	1.96	2.775 (4)	178
C3—H3A⋯O2	0.93	2.47	2.928 (5)	110
C11—H11A⋯O2	0.93	2.49	2.939 (5)	110
Symmetry codes: (i) $[-x+1, y, -z+{\script{3\over 2}}]$ ; (ii) x, y-1, z.

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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, Ils. DOI: 10.1107/S1600536808016681/hk2469sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808016681/hk2469Isup2.hkl

checkCIF report

Comment top

2-(Bis(3,5-dimethylphenyl)phosphoryl)propan-2-ol was first synthesized by the nucleophillic addition of acetone with di(3,5-dimethylphenyl)phosphine oxide at room temperature. We report herein its crystal structure.

In the molecule of the title compound, (I), (Fig. 1) the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6) and B (C10-C15) are, of course, planar, and the dihedral angle between them is A/B = 54.04 (3)°. The intramolecular C-H···O hydrogen bonds (Table 1) result in the formation of two five-membered planar rings: C (C3/C4/P/O2/H3A) and D (C11/C12/P/O2/H11A). The dihedral angles between the adjacent rings are A/C = 2.66 (3)° and B/D = 2.79 (3)°. So, rings A, C and B, D are nearly coplanar. The coplanar ring systems are oriented at a dihedral angle of 54.70 (3)°.

In the crystal structure, intermolecular O-H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For related literature, see: Takao & Kazuhiko (1997). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound, (I) was synthesized by the reaction of di(3,5-dimethyl- phenyl)phosphine oxide (0.20 g, 0.70 mmol) (Takao & Kazuhiko, 1997) and acetone (25 ml). Crystals suitable for X-ray analysis were obtained by dissolving (I) in acetone and evaporating the solvent slowly at room temperature for about 7 d.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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 the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level. Hydrogen bonds are shown as dashed lines.
	Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.

2-[Bis(3,5-dimethylphenyl)phosphoryl]propan-2-ol hemihydrate top

Crystal data top

C₁₉H₂₅O₂P·0.5H₂O	F(000) = 1396
M_r = 324.87	D_x = 1.179 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 30.129 (6) Å	θ = 9–12°
b = 6.2830 (13) Å	µ = 0.16 mm⁻¹
c = 20.192 (4) Å	T = 298 K
β = 106.76 (3)°	Needle, colorless
V = 3660.1 (14) Å³	0.20 × 0.10 × 0.10 mm
Z = 8

Data collection top

Enraf–Nonius CAD-4 diffractometer	1904 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.049
Graphite monochromator	θ_max = 25.2°, θ_min = 1.4°
ω/2θ scans	h = −36→34
Absorption correction: ψ scan (North et al., 1968)	k = 0→7
T_min = 0.969, T_max = 0.984	l = 0→24
6573 measured reflections	3 standard reflections every 120 min
3298 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.205	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
3298 reflections	(Δ/σ)_max = 0.001
206 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.55 e Å⁻³

Crystal data top

C₁₉H₂₅O₂P·0.5H₂O	V = 3660.1 (14) Å³
M_r = 324.87	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 30.129 (6) Å	µ = 0.16 mm⁻¹
b = 6.2830 (13) Å	T = 298 K
c = 20.192 (4) Å	0.20 × 0.10 × 0.10 mm
β = 106.76 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1904 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.049
T_min = 0.969, T_max = 0.984	3 standard reflections every 120 min
6573 measured reflections	intensity decay: none
3298 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.205	H-atom parameters constrained
S = 1.03	Δρ_max = 0.49 e Å⁻³
3298 reflections	Δρ_min = −0.55 e Å⁻³
206 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
P	0.40003 (3)	0.20845 (15)	0.59292 (5)	0.0338 (3)
OW	0.5000	0.4938 (10)	0.7500	0.146 (3)
HWA	0.5127	0.5453	0.7899	0.175*	0.50
O1	0.39553 (9)	−0.2053 (4)	0.58847 (14)	0.0526 (8)
H1A	0.4058	−0.3239	0.6013	0.079*
C1	0.44847 (16)	0.5766 (9)	0.3932 (3)	0.0735 (15)
H1B	0.4461	0.5651	0.3449	0.110*
H1C	0.4804	0.5651	0.4199	0.110*
H1D	0.4364	0.7117	0.4020	0.110*
O2	0.42908 (8)	0.3898 (4)	0.62967 (13)	0.0428 (7)
C2	0.42087 (13)	0.3997 (7)	0.4134 (2)	0.0493 (10)
C3	0.41939 (12)	0.3820 (6)	0.4812 (2)	0.0434 (9)
H3A	0.4345	0.4833	0.5135	0.052*
C4	0.39592 (11)	0.2167 (6)	0.50207 (18)	0.0371 (8)
C5	0.37267 (12)	0.0663 (6)	0.45310 (19)	0.0425 (9)
H5A	0.3567	−0.0450	0.4664	0.051*
C6	0.37332 (13)	0.0829 (7)	0.3851 (2)	0.0485 (11)
C7	0.39760 (14)	0.2487 (7)	0.3663 (2)	0.0538 (11)
H7A	0.3982	0.2587	0.3206	0.065*
C8	0.34811 (16)	−0.0813 (9)	0.3322 (2)	0.0685 (14)
H8A	0.3523	−0.0481	0.2880	0.103*
H8B	0.3157	−0.0793	0.3288	0.103*
H8C	0.3605	−0.2202	0.3465	0.103*
C9	0.28814 (17)	0.5685 (10)	0.7141 (3)	0.0817 (17)
H9A	0.2571	0.5631	0.7178	0.123*
H9B	0.2937	0.7059	0.6973	0.123*
H9C	0.3097	0.5442	0.7587	0.123*
C10	0.29420 (14)	0.3982 (7)	0.6642 (2)	0.0515 (11)
C11	0.33647 (13)	0.3767 (6)	0.65031 (19)	0.0437 (9)
H11A	0.3607	0.4685	0.6710	0.052*
C12	0.34291 (12)	0.2187 (6)	0.60557 (17)	0.0350 (8)
C13	0.30647 (12)	0.0836 (6)	0.57377 (19)	0.0405 (9)
H13A	0.3107	−0.0214	0.5437	0.049*
C14	0.26351 (13)	0.1041 (7)	0.5865 (2)	0.0452 (10)
C15	0.25866 (14)	0.2611 (7)	0.6316 (2)	0.0489 (10)
H15A	0.2302	0.2755	0.6405	0.059*
C16	0.22411 (15)	−0.0427 (8)	0.5522 (3)	0.0649 (13)
H16A	0.2189	−0.0389	0.5030	0.097*
H16B	0.1965	0.0025	0.5629	0.097*
H16C	0.2317	−0.1852	0.5687	0.097*
C17	0.42596 (12)	−0.0481 (6)	0.62715 (19)	0.0369 (8)
C18	0.42841 (16)	−0.0606 (7)	0.7034 (2)	0.0587 (12)
H18A	0.4425	−0.1927	0.7222	0.088*
H18B	0.3977	−0.0528	0.7082	0.088*
H18C	0.4466	0.0558	0.7277	0.088*
C19	0.47388 (13)	−0.0667 (7)	0.6165 (2)	0.0540 (11)
H19A	0.4874	−0.2009	0.6343	0.081*
H19B	0.4932	0.0469	0.6406	0.081*
H19C	0.4712	−0.0577	0.5681	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P	0.0353 (5)	0.0217 (5)	0.0407 (5)	−0.0001 (4)	0.0049 (4)	0.0001 (4)
OW	0.183 (7)	0.085 (5)	0.102 (5)	0.000	−0.065 (5)	0.000
O1	0.0576 (17)	0.0242 (13)	0.0655 (18)	−0.0009 (13)	0.0012 (14)	0.0037 (13)
C1	0.065 (3)	0.073 (3)	0.094 (4)	0.003 (3)	0.041 (3)	0.018 (3)
O2	0.0418 (14)	0.0225 (13)	0.0552 (17)	−0.0023 (12)	−0.0003 (12)	−0.0026 (12)
C2	0.042 (2)	0.049 (3)	0.061 (3)	0.009 (2)	0.023 (2)	0.012 (2)
C3	0.042 (2)	0.036 (2)	0.051 (2)	0.0029 (18)	0.0110 (18)	0.0028 (19)
C4	0.0331 (18)	0.0357 (19)	0.041 (2)	0.0043 (17)	0.0092 (15)	0.0052 (17)
C5	0.038 (2)	0.044 (2)	0.045 (2)	−0.0040 (18)	0.0094 (17)	0.0009 (19)
C6	0.042 (2)	0.060 (3)	0.042 (2)	0.006 (2)	0.0092 (18)	−0.008 (2)
C7	0.052 (2)	0.068 (3)	0.045 (2)	0.013 (2)	0.0178 (19)	0.010 (2)
C8	0.070 (3)	0.081 (4)	0.048 (3)	0.003 (3)	0.007 (2)	−0.020 (3)
C9	0.070 (3)	0.091 (4)	0.086 (4)	0.008 (3)	0.026 (3)	−0.044 (3)
C10	0.049 (2)	0.049 (3)	0.055 (3)	0.005 (2)	0.012 (2)	−0.010 (2)
C11	0.042 (2)	0.040 (2)	0.044 (2)	−0.0018 (19)	0.0036 (17)	−0.0072 (19)
C12	0.044 (2)	0.0252 (17)	0.0344 (18)	0.0025 (16)	0.0082 (15)	0.0033 (16)
C13	0.045 (2)	0.028 (2)	0.045 (2)	−0.0007 (17)	0.0090 (17)	−0.0051 (17)
C14	0.039 (2)	0.044 (2)	0.052 (2)	−0.0008 (19)	0.0119 (18)	0.002 (2)
C15	0.043 (2)	0.049 (3)	0.055 (2)	0.007 (2)	0.0163 (19)	0.002 (2)
C16	0.044 (2)	0.066 (3)	0.082 (3)	−0.012 (2)	0.013 (2)	−0.007 (3)
C17	0.0374 (19)	0.0245 (17)	0.046 (2)	0.0037 (16)	0.0073 (16)	0.0044 (16)
C18	0.076 (3)	0.045 (3)	0.053 (3)	0.011 (2)	0.016 (2)	0.011 (2)
C19	0.042 (2)	0.046 (2)	0.072 (3)	0.010 (2)	0.014 (2)	0.009 (2)

Geometric parameters (Å, º) top

P—O2	1.497 (2)	C9—H9A	0.9600
P—C4	1.803 (4)	C9—H9B	0.9600
P—C12	1.812 (4)	C9—H9C	0.9600
P—C17	1.837 (4)	C10—C15	1.384 (6)
OW—HWA	0.8500	C10—C11	1.387 (5)
O1—C17	1.419 (4)	C11—C12	1.393 (5)
O1—H1A	0.8200	C11—H11A	0.9300
C1—C2	1.513 (6)	C12—C13	1.390 (5)
C1—H1B	0.9600	C13—C14	1.397 (5)
C1—H1C	0.9600	C13—H13A	0.9300
C1—H1D	0.9600	C14—C15	1.378 (6)
C2—C7	1.383 (6)	C14—C16	1.505 (6)
C2—C3	1.388 (5)	C15—H15A	0.9300
C3—C4	1.389 (5)	C16—H16A	0.9600
C3—H3A	0.9300	C16—H16B	0.9600
C4—C5	1.400 (5)	C16—H16C	0.9600
C5—C6	1.383 (5)	C17—C18	1.521 (5)
C5—H5A	0.9300	C17—C19	1.524 (5)
C6—C7	1.388 (6)	C18—H18A	0.9600
C6—C8	1.521 (6)	C18—H18B	0.9600
C7—H7A	0.9300	C18—H18C	0.9600
C8—H8A	0.9600	C19—H19A	0.9600
C8—H8B	0.9600	C19—H19B	0.9600
C8—H8C	0.9600	C19—H19C	0.9600
C9—C10	1.516 (6)

O2—P—C4	109.95 (17)	C15—C10—C11	118.2 (4)
O2—P—C12	110.28 (16)	C15—C10—C9	122.0 (4)
C4—P—C12	110.66 (16)	C11—C10—C9	119.8 (4)
O2—P—C17	110.91 (15)	C10—C11—C12	120.5 (4)
C4—P—C17	107.75 (18)	C10—C11—H11A	119.7
C12—P—C17	107.23 (17)	C12—C11—H11A	119.7
C17—O1—H1A	109.5	C13—C12—C11	119.7 (3)
C2—C1—H1B	109.5	C13—C12—P	124.7 (3)
C2—C1—H1C	109.5	C11—C12—P	115.6 (3)
H1B—C1—H1C	109.5	C12—C13—C14	120.6 (3)
C2—C1—H1D	109.5	C12—C13—H13A	119.7
H1B—C1—H1D	109.5	C14—C13—H13A	119.7
H1C—C1—H1D	109.5	C15—C14—C13	117.9 (4)
C7—C2—C3	118.0 (4)	C15—C14—C16	121.5 (4)
C7—C2—C1	121.8 (4)	C13—C14—C16	120.5 (4)
C3—C2—C1	120.1 (4)	C14—C15—C10	123.0 (4)
C2—C3—C4	121.5 (4)	C14—C15—H15A	118.5
C2—C3—H3A	119.2	C10—C15—H15A	118.5
C4—C3—H3A	119.2	C14—C16—H16A	109.5
C3—C4—C5	119.0 (4)	C14—C16—H16B	109.5
C3—C4—P	116.0 (3)	H16A—C16—H16B	109.5
C5—C4—P	124.9 (3)	C14—C16—H16C	109.5
C6—C5—C4	120.2 (4)	H16A—C16—H16C	109.5
C6—C5—H5A	119.9	H16B—C16—H16C	109.5
C4—C5—H5A	119.9	O1—C17—C18	110.9 (3)
C5—C6—C7	119.2 (4)	O1—C17—C19	110.9 (3)
C5—C6—C8	119.9 (4)	C18—C17—C19	111.5 (3)
C7—C6—C8	120.9 (4)	O1—C17—P	105.5 (2)
C2—C7—C6	122.0 (4)	C18—C17—P	108.5 (3)
C2—C7—H7A	119.0	C19—C17—P	109.4 (3)
C6—C7—H7A	119.0	C17—C18—H18A	109.5
C6—C8—H8A	109.5	C17—C18—H18B	109.5
C6—C8—H8B	109.5	H18A—C18—H18B	109.5
H8A—C8—H8B	109.5	C17—C18—H18C	109.5
C6—C8—H8C	109.5	H18A—C18—H18C	109.5
H8A—C8—H8C	109.5	H18B—C18—H18C	109.5
H8B—C8—H8C	109.5	C17—C19—H19A	109.5
C10—C9—H9A	109.5	C17—C19—H19B	109.5
C10—C9—H9B	109.5	H19A—C19—H19B	109.5
H9A—C9—H9B	109.5	C17—C19—H19C	109.5
C10—C9—H9C	109.5	H19A—C19—H19C	109.5
H9A—C9—H9C	109.5	H19B—C19—H19C	109.5
H9B—C9—H9C	109.5

C7—C2—C3—C4	0.9 (6)	C4—P—C12—C13	52.7 (4)
C1—C2—C3—C4	−177.4 (4)	C17—P—C12—C13	−64.6 (3)
C2—C3—C4—C5	−1.0 (5)	O2—P—C12—C11	−4.9 (3)
C2—C3—C4—P	176.7 (3)	C4—P—C12—C11	−126.8 (3)
O2—P—C4—C3	0.2 (3)	C17—P—C12—C11	116.0 (3)
C12—P—C4—C3	122.3 (3)	C11—C12—C13—C14	−0.3 (5)
C17—P—C4—C3	−120.8 (3)	P—C12—C13—C14	−179.8 (3)
O2—P—C4—C5	177.7 (3)	C12—C13—C14—C15	−0.3 (6)
C12—P—C4—C5	−60.3 (4)	C12—C13—C14—C16	−179.9 (4)
C17—P—C4—C5	56.7 (3)	C13—C14—C15—C10	0.2 (6)
C3—C4—C5—C6	0.2 (5)	C16—C14—C15—C10	179.8 (4)
P—C4—C5—C6	−177.2 (3)	C11—C10—C15—C14	0.4 (7)
C4—C5—C6—C7	0.6 (6)	C9—C10—C15—C14	−179.5 (4)
C4—C5—C6—C8	179.8 (4)	O2—P—C17—O1	−179.9 (2)
C3—C2—C7—C6	−0.1 (6)	C4—P—C17—O1	−59.6 (3)
C1—C2—C7—C6	178.2 (4)	C12—P—C17—O1	59.6 (3)
C5—C6—C7—C2	−0.7 (6)	O2—P—C17—C18	61.2 (3)
C8—C6—C7—C2	−179.9 (4)	C4—P—C17—C18	−178.4 (3)
C15—C10—C11—C12	−1.0 (6)	C12—P—C17—C18	−59.2 (3)
C9—C10—C11—C12	178.8 (4)	O2—P—C17—C19	−60.6 (3)
C10—C11—C12—C13	1.0 (6)	C4—P—C17—C19	59.8 (3)
C10—C11—C12—P	−179.5 (3)	C12—P—C17—C19	178.9 (3)
O2—P—C12—C13	174.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
OW—HWA···O2ⁱ	0.85	2.24	2.811 (3)	124
O1—H1A···O2ⁱⁱ	0.82	1.96	2.775 (4)	178
C3—H3A···O2	0.93	2.47	2.928 (5)	110
C11—H11A···O2	0.93	2.49	2.939 (5)	110

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₅O₂P·0.5H₂O
M_r	324.87
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	30.129 (6), 6.2830 (13), 20.192 (4)
β (°)	106.76 (3)
V (Å³)	3660.1 (14)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.969, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	6573, 3298, 1904
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.205, 1.03
No. of reflections	3298
No. of parameters	206
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.55

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), 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
OW—HWA···O2ⁱ	0.85	2.24	2.811 (3)	124.00
O1—H1A···O2ⁱⁱ	0.82	1.96	2.775 (4)	178.00
C3—H3A···O2	0.93	2.47	2.928 (5)	110.00
C11—H11A···O2	0.93	2.49	2.939 (5)	110.00

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) x, y−1, z.

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for its support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Enraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Takao, S. & Kazuhiko, M. (1997). EP Patent No. 0 755 937. Google Scholar