(Rp)-2-Isopropyl-5-methyl­cyclo­hexyl isoprop­yl(phen­yl)phosphinate

Liu, L.-J.; Xu, H.; Meng, F.-J.; Wang, D.-Q.; Zhao, C.-Q.

doi:10.1107/S1600536811013390

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1186

doi:10.1107/S1600536811013390

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(R_p)-2-Isopropyl-5-methylcyclohexyl isopropyl(phenyl)phosphinate

Li-Juan Liu,^a Hao Xu,^a Fan-Jie Meng,^a Da-Qi Wang ^a and Chang-Qiu Zhao ^a ^*

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: literabc@hotmail.com

(Received 13 March 2011; accepted 10 April 2011; online 22 April 2011)

The title compound, C₁₉H₃₁O₂P, features a distorted tetrahedral P atom that bonds to the phenyl ring, isopropyl and 2-isopropyl-5-methylcyclohexyl groups, and is determined as having an R_p configuration. A chair conformation is observed for the cyclohexyl ring. In the crystal, molecules are linked into chains running along the a axis by weak intermolecular C—H⋯O hodrogen bonds.

Related literature

For general background to P-chiral compounds and for related structures, see: Chaloner et al. (1991 ); Fu & Zhao et al. (2010 ).

Experimental

Crystal data

C₁₉H₃₁O₂P
M_r = 322.41
Monoclinic, P 2₁
a = 5.8847 (4) Å
b = 17.196 (3) Å
c = 9.7075 (9) Å
β = 95.184 (1)°
V = 978.3 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 298 K
0.35 × 0.16 × 0.14 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.951, T_max = 0.980
4964 measured reflections
3175 independent reflections
1991 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.073
S = 1.00
3175 reflections
205 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.16 e Å⁻³
Absolute structure: Flack (1983 ), 1775 Friedel pairs
Flack parameter: 0.02 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯O2ⁱ	0.98	2.44	3.180 (4)	132
Symmetry code: (i) x+1, y, z.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811013390/xu5176sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811013390/xu5176Isup2.hkl

checkCIF report

Comment top

The P-chiral compound has been reported previously (Chaloner et al., 1991). We recently reported the crystal stucture of (R_p)-α-hydroxy-cyclohexyl-menthyl phenylphosphinate, a compound readily synthesized by addition of (R_p)-phenylphosphinate to cyclohexanone (Fu & Zhao, 2010). Herein we report a similar compound which is obtained by reaction of O-menthyl phenylphosphoryl chloride and isopropyl magnesium chloride.

A stable chair conformation is observed for the cyclohexane ring of the 2-isopropyl-5-methylcyclohexyloxy, in which the isopropyl, methyl and oxygen atom locate at equatorial bond. The absolute configuration of C₁, C₃, and C₄ are R, R, and S, respectively (Fig.1). In this P-chiral title compound, the configuration of the central P atom is R and four groups around the P atom form an irregular tetrahedron. The bond angle of C11—P1—C17 is 107.61 (17)°, O1—P1—C11 is 105.66 (14)°, O1—P1—C17 is 101.39 (13)°, O2—P1—O1 is 115.03 (12)°, O2—P1—C17 is 114.76 (15)° and O2—P1—C11 is 111.50 (17)° (Chaloner et al. 1991). In the crystal structure, intermolecular C17—H17···O2 hodrogen bonds connect molecules into a one-dimensional chain (Fig.2).

Related literature top

For general background to P-chiral compounds and for related structures, see: Chaloner et al. (1991); Fu & Zhao et al. (2010).

Experimental top

O-Menthyl phenylphosphoryl chloride (0.3 mmol) was added to a stirred ether solution of isopropyl magnesium chloride (0.6 mmol) in a Schlenk tube under nitrogen, and the mixture was stirred for 24 h at room temperature. After washing with water, the resulting solution was purified by silica gel plate to afford the title compound. The crystal suit for X-ray diffraction was obtained from recrystallization with ethyl ether/hexane.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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 compound, showing the atomic numbering scheme with 30% probability displacement ellipsoids.
	Fig. 2. A view of the one-dimensional chain structure formed by C—H···O hodrogen bonds in the title compound. H atoms not involved in hydrogen bondings have been omitted for clarity. [Symmetry codes: (i) x + 1, y, z]

(R_p)-2-Isopropyl-5-methylcyclohexyl isopropyl(phenyl)phosphinate top

Crystal data top

C₁₉H₃₁O₂P	F(000) = 352
M_r = 322.41	D_x = 1.094 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1152 reflections
a = 5.8847 (4) Å	θ = 3.2–18.6°
b = 17.196 (3) Å	µ = 0.15 mm⁻¹
c = 9.7075 (9) Å	T = 298 K
β = 95.184 (1)°	Block, colorless
V = 978.3 (2) Å³	0.35 × 0.16 × 0.14 mm
Z = 2

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3175 independent reflections
Radiation source: fine-focus sealed tube	1991 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→7
T_min = 0.951, T_max = 0.980	k = −20→20
4964 measured reflections	l = −9→11

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)] = 0.047	H-atom parameters constrained
wR(F²) = 0.073	w = 1/[σ²(F_o²) + (0.0093P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
3175 reflections	Δρ_max = 0.22 e Å⁻³
205 parameters	Δρ_min = −0.16 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1775 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (11)

Crystal data top

C₁₉H₃₁O₂P	V = 978.3 (2) Å³
M_r = 322.41	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 5.8847 (4) Å	µ = 0.15 mm⁻¹
b = 17.196 (3) Å	T = 298 K
c = 9.7075 (9) Å	0.35 × 0.16 × 0.14 mm
β = 95.184 (1)°

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3175 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1991 reflections with I > 2σ(I)
T_min = 0.951, T_max = 0.980	R_int = 0.045
4964 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.073	Δρ_max = 0.22 e Å⁻³
S = 1.00	Δρ_min = −0.16 e Å⁻³
3175 reflections	Absolute structure: Flack (1983), 1775 Friedel pairs
205 parameters	Absolute structure parameter: 0.02 (11)
1 restraint

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 > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
P1	0.58068 (16)	0.52850 (6)	0.70438 (9)	0.0580 (2)
O1	0.6203 (3)	0.51752 (13)	0.86663 (18)	0.0574 (6)
O2	0.3626 (4)	0.56419 (13)	0.6548 (2)	0.0764 (8)
C1	0.1496 (7)	0.5651 (2)	1.0974 (3)	0.0740 (11)
H1	0.0193	0.5439	1.0393	0.089*
C2	0.3498 (6)	0.57668 (19)	1.0062 (3)	0.0657 (10)
H2A	0.3025	0.6119	0.9310	0.079*
H2B	0.4772	0.6003	1.0612	0.079*
C3	0.4266 (5)	0.50056 (18)	0.9469 (3)	0.0565 (10)
H3	0.3015	0.4784	0.8857	0.068*
C4	0.5012 (6)	0.4420 (2)	1.0600 (3)	0.0633 (10)
H4	0.6252	0.4662	1.1192	0.076*
C5	0.3002 (7)	0.4311 (2)	1.1490 (4)	0.0801 (12)
H5A	0.1737	0.4076	1.0927	0.096*
H5B	0.3456	0.3954	1.2239	0.096*
C6	0.2205 (7)	0.5062 (2)	1.2093 (4)	0.0858 (13)
H6A	0.3427	0.5279	1.2714	0.103*
H6B	0.0923	0.4957	1.2626	0.103*
C7	0.0780 (7)	0.6421 (2)	1.1575 (4)	0.1057 (15)
H7A	0.2041	0.6638	1.2145	0.159*
H7B	−0.0475	0.6336	1.2124	0.159*
H7C	0.0323	0.6775	1.0837	0.159*
C8	0.5943 (7)	0.3651 (2)	1.0072 (4)	0.0768 (12)
H8	0.7117	0.3787	0.9459	0.092*
C9	0.4161 (8)	0.3168 (2)	0.9222 (4)	0.1041 (15)
H9A	0.4885	0.2731	0.8831	0.156*
H9B	0.3433	0.3482	0.8492	0.156*
H9C	0.3039	0.2988	0.9806	0.156*
C10	0.7115 (7)	0.3175 (2)	1.1254 (4)	0.1071 (15)
H10A	0.5986	0.2963	1.1802	0.161*
H10B	0.8137	0.3502	1.1820	0.161*
H10C	0.7960	0.2758	1.0883	0.161*
C11	0.6101 (7)	0.4337 (2)	0.6323 (3)	0.0630 (10)
C12	0.8067 (8)	0.3905 (2)	0.6580 (4)	0.0767 (12)
H12	0.9302	0.4118	0.7116	0.092*
C13	0.8240 (9)	0.3154 (3)	0.6050 (4)	0.0929 (13)
H13	0.9577	0.2870	0.6235	0.112*
C14	0.6443 (10)	0.2842 (3)	0.5264 (5)	0.0956 (15)
H14	0.6557	0.2344	0.4900	0.115*
C15	0.4474 (9)	0.3255 (3)	0.5005 (4)	0.0925 (14)
H15	0.3240	0.3035	0.4478	0.111*
C16	0.4299 (7)	0.4003 (2)	0.5524 (4)	0.0777 (12)
H16	0.2955	0.4282	0.5331	0.093*
C17	0.8282 (6)	0.58385 (19)	0.6703 (3)	0.0597 (9)
H17	0.9645	0.5550	0.7063	0.072*
C18	0.8349 (7)	0.5941 (2)	0.5134 (3)	0.0848 (12)
H18A	0.7075	0.6252	0.4776	0.127*
H18B	0.8271	0.5441	0.4694	0.127*
H18C	0.9744	0.6195	0.4952	0.127*
C19	0.8278 (7)	0.66248 (18)	0.7434 (4)	0.0817 (13)
H19A	0.9603	0.6916	0.7238	0.123*
H19B	0.8300	0.6545	0.8414	0.123*
H19C	0.6928	0.6908	0.7111	0.123*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0455 (6)	0.0754 (6)	0.0541 (5)	0.0036 (6)	0.0104 (4)	0.0064 (5)
O1	0.0461 (14)	0.0737 (16)	0.0541 (13)	−0.0016 (13)	0.0140 (10)	0.0055 (12)
O2	0.0450 (16)	0.113 (2)	0.0721 (15)	0.0172 (13)	0.0087 (12)	0.0088 (13)
C1	0.075 (3)	0.090 (3)	0.059 (2)	0.007 (2)	0.021 (2)	0.001 (2)
C2	0.067 (3)	0.073 (3)	0.059 (2)	−0.001 (2)	0.0167 (19)	0.0001 (19)
C3	0.052 (2)	0.071 (3)	0.049 (2)	−0.0088 (19)	0.0133 (18)	0.0024 (18)
C4	0.067 (3)	0.069 (3)	0.056 (2)	−0.004 (2)	0.015 (2)	0.005 (2)
C5	0.084 (3)	0.087 (3)	0.073 (3)	0.000 (2)	0.027 (2)	0.018 (2)
C6	0.090 (3)	0.106 (4)	0.066 (3)	0.000 (3)	0.033 (2)	0.002 (2)
C7	0.123 (4)	0.109 (4)	0.091 (3)	0.030 (3)	0.044 (3)	−0.012 (2)
C8	0.081 (3)	0.075 (3)	0.079 (3)	0.006 (2)	0.029 (2)	0.021 (2)
C9	0.126 (4)	0.084 (3)	0.104 (4)	−0.005 (3)	0.019 (3)	−0.006 (3)
C10	0.111 (4)	0.101 (4)	0.112 (4)	0.014 (3)	0.029 (3)	0.030 (3)
C11	0.057 (3)	0.081 (3)	0.052 (2)	−0.004 (2)	0.012 (2)	0.004 (2)
C12	0.064 (3)	0.082 (3)	0.085 (3)	−0.001 (2)	0.013 (2)	−0.007 (2)
C13	0.094 (4)	0.090 (4)	0.097 (4)	0.010 (3)	0.025 (3)	0.001 (3)
C14	0.116 (5)	0.087 (4)	0.087 (4)	−0.004 (4)	0.026 (3)	−0.015 (3)
C15	0.104 (5)	0.106 (4)	0.069 (3)	−0.029 (3)	0.009 (3)	−0.014 (3)
C16	0.073 (3)	0.098 (4)	0.062 (3)	−0.007 (3)	0.008 (2)	−0.003 (2)
C17	0.049 (2)	0.072 (3)	0.060 (2)	0.0058 (19)	0.0132 (17)	0.0110 (19)
C18	0.087 (3)	0.099 (3)	0.072 (3)	−0.009 (3)	0.028 (2)	0.020 (2)
C19	0.090 (3)	0.068 (3)	0.088 (3)	−0.008 (2)	0.012 (2)	0.009 (2)

Geometric parameters (Å, º) top

P1—O2	1.464 (2)	C8—H8	0.9800
P1—O1	1.5826 (19)	C9—H9A	0.9600
P1—C11	1.789 (4)	C9—H9B	0.9600
P1—C17	1.795 (3)	C9—H9C	0.9600
O1—C3	1.467 (3)	C10—H10A	0.9600
C1—C6	1.515 (4)	C10—H10B	0.9600
C1—C7	1.522 (4)	C10—H10C	0.9600
C1—C2	1.549 (4)	C11—C12	1.378 (5)
C1—H1	0.9800	C11—C16	1.381 (4)
C2—C3	1.515 (4)	C12—C13	1.398 (5)
C2—H2A	0.9700	C12—H12	0.9300
C2—H2B	0.9700	C13—C14	1.358 (6)
C3—C4	1.525 (4)	C13—H13	0.9300
C3—H3	0.9800	C14—C15	1.363 (6)
C4—C8	1.537 (5)	C14—H14	0.9300
C4—C5	1.538 (4)	C15—C16	1.388 (5)
C4—H4	0.9800	C15—H15	0.9300
C5—C6	1.511 (4)	C16—H16	0.9300
C5—H5A	0.9700	C17—C19	1.527 (4)
C5—H5B	0.9700	C17—C18	1.537 (4)
C6—H6A	0.9700	C17—H17	0.9800
C6—H6B	0.9700	C18—H18A	0.9600
C7—H7A	0.9600	C18—H18B	0.9600
C7—H7B	0.9600	C18—H18C	0.9600
C7—H7C	0.9600	C19—H19A	0.9600
C8—C9	1.521 (5)	C19—H19B	0.9600
C8—C10	1.523 (5)	C19—H19C	0.9600

O2—P1—O1	115.03 (12)	C9—C8—H8	106.8
O2—P1—C11	111.50 (17)	C10—C8—H8	106.8
O1—P1—C11	105.66 (14)	C4—C8—H8	106.8
O2—P1—C17	114.76 (15)	C8—C9—H9A	109.5
O1—P1—C17	101.39 (13)	C8—C9—H9B	109.5
C11—P1—C17	107.61 (17)	H9A—C9—H9B	109.5
C3—O1—P1	120.03 (18)	C8—C9—H9C	109.5
C6—C1—C7	112.0 (3)	H9A—C9—H9C	109.5
C6—C1—C2	108.7 (3)	H9B—C9—H9C	109.5
C7—C1—C2	111.0 (3)	C8—C10—H10A	109.5
C6—C1—H1	108.3	C8—C10—H10B	109.5
C7—C1—H1	108.3	H10A—C10—H10B	109.5
C2—C1—H1	108.3	C8—C10—H10C	109.5
C3—C2—C1	112.0 (3)	H10A—C10—H10C	109.5
C3—C2—H2A	109.2	H10B—C10—H10C	109.5
C1—C2—H2A	109.2	C12—C11—C16	117.9 (4)
C3—C2—H2B	109.2	C12—C11—P1	121.9 (3)
C1—C2—H2B	109.2	C16—C11—P1	120.2 (3)
H2A—C2—H2B	107.9	C11—C12—C13	121.3 (4)
O1—C3—C2	107.6 (2)	C11—C12—H12	119.4
O1—C3—C4	109.1 (3)	C13—C12—H12	119.4
C2—C3—C4	111.9 (3)	C14—C13—C12	119.6 (4)
O1—C3—H3	109.4	C14—C13—H13	120.2
C2—C3—H3	109.4	C12—C13—H13	120.2
C4—C3—H3	109.4	C13—C14—C15	120.2 (5)
C3—C4—C8	114.6 (3)	C13—C14—H14	119.9
C3—C4—C5	107.4 (3)	C15—C14—H14	119.9
C8—C4—C5	113.4 (3)	C14—C15—C16	120.4 (5)
C3—C4—H4	107.0	C14—C15—H15	119.8
C8—C4—H4	107.0	C16—C15—H15	119.8
C5—C4—H4	107.0	C11—C16—C15	120.7 (4)
C6—C5—C4	113.2 (3)	C11—C16—H16	119.6
C6—C5—H5A	108.9	C15—C16—H16	119.6
C4—C5—H5A	108.9	C19—C17—C18	111.1 (3)
C6—C5—H5B	108.9	C19—C17—P1	110.4 (2)
C4—C5—H5B	108.9	C18—C17—P1	109.7 (2)
H5A—C5—H5B	107.7	C19—C17—H17	108.5
C5—C6—C1	111.6 (3)	C18—C17—H17	108.5
C5—C6—H6A	109.3	P1—C17—H17	108.5
C1—C6—H6A	109.3	C17—C18—H18A	109.5
C5—C6—H6B	109.3	C17—C18—H18B	109.5
C1—C6—H6B	109.3	H18A—C18—H18B	109.5
H6A—C6—H6B	108.0	C17—C18—H18C	109.5
C1—C7—H7A	109.5	H18A—C18—H18C	109.5
C1—C7—H7B	109.5	H18B—C18—H18C	109.5
H7A—C7—H7B	109.5	C17—C19—H19A	109.5
C1—C7—H7C	109.5	C17—C19—H19B	109.5
H7A—C7—H7C	109.5	H19A—C19—H19B	109.5
H7B—C7—H7C	109.5	C17—C19—H19C	109.5
C9—C8—C10	111.0 (3)	H19A—C19—H19C	109.5
C9—C8—C4	113.7 (3)	H19B—C19—H19C	109.5
C10—C8—C4	111.3 (3)

O2—P1—O1—C3	33.5 (3)	C5—C4—C8—C10	−68.5 (4)
C11—P1—O1—C3	−89.9 (3)	O2—P1—C11—C12	176.4 (3)
C17—P1—O1—C3	157.9 (2)	O1—P1—C11—C12	−58.0 (3)
C6—C1—C2—C3	55.5 (4)	C17—P1—C11—C12	49.7 (3)
C7—C1—C2—C3	179.1 (3)	O2—P1—C11—C16	−6.1 (3)
P1—O1—C3—C2	−97.1 (3)	O1—P1—C11—C16	119.6 (3)
P1—O1—C3—C4	141.3 (2)	C17—P1—C11—C16	−132.7 (3)
C1—C2—C3—O1	−178.1 (3)	C16—C11—C12—C13	0.0 (5)
C1—C2—C3—C4	−58.3 (4)	P1—C11—C12—C13	177.6 (3)
O1—C3—C4—C8	−57.7 (4)	C11—C12—C13—C14	0.2 (6)
C2—C3—C4—C8	−176.6 (3)	C12—C13—C14—C15	−0.7 (7)
O1—C3—C4—C5	175.3 (3)	C13—C14—C15—C16	1.1 (7)
C2—C3—C4—C5	56.4 (4)	C12—C11—C16—C15	0.3 (6)
C3—C4—C5—C6	−56.6 (4)	P1—C11—C16—C15	−177.4 (3)
C8—C4—C5—C6	175.8 (3)	C14—C15—C16—C11	−0.8 (6)
C4—C5—C6—C1	57.9 (5)	O2—P1—C17—C19	61.8 (3)
C7—C1—C6—C5	−177.8 (4)	O1—P1—C17—C19	−62.8 (3)
C2—C1—C6—C5	−54.7 (4)	C11—P1—C17—C19	−173.5 (2)
C3—C4—C8—C9	−66.2 (4)	O2—P1—C17—C18	−61.0 (3)
C5—C4—C8—C9	57.7 (4)	O1—P1—C17—C18	174.4 (2)
C3—C4—C8—C10	167.7 (3)	C11—P1—C17—C18	63.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O2ⁱ	0.98	2.44	3.180 (4)	132

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₃₁O₂P
M_r	322.41
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	5.8847 (4), 17.196 (3), 9.7075 (9)
β (°)	95.184 (1)
V (Å³)	978.3 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.35 × 0.16 × 0.14

Data collection
Diffractometer	Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.951, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	4964, 3175, 1991
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.073, 1.00
No. of reflections	3175
No. of parameters	205
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.16
Absolute structure	Flack (1983), 1775 Friedel pairs
Absolute structure parameter	0.02 (11)

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O2ⁱ	0.98	2.44	3.180 (4)	132

Symmetry code: (i) x+1, y, z.

Acknowledgements

We acknowledge financial support by the Natural Science Foundation of China (No. 20772055).

References

Chaloner, P. A., Harrison, R. M. & Hitchcock, P. B. (1991). Acta Cryst. C47, 2241–2242. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Fu, B. & Zhao, C.-Q. (2010). Acta Cryst. E66, o859. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar