Diethyl [4-(1,3-benzothia­zol-2-yl)benz­yl]phospho­nate

Peng, R.; Li, H.

doi:10.1107/S1600536810047045

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3236

https://doi.org/10.1107/S1600536810047045

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Diethyl [4-(1,3-benzothiazol-2-yl)benzyl]phosphonate

Rong Peng ^a ^* and Huisheng Li ^a

^aDepartment of Chemistry and Biology, Xiangfan University, Xiangfan 441053, People's Republic of China
^*Correspondence e-mail: cch510@126.com

(Received 5 November 2010; accepted 13 November 2010; online 20 November 2010)

In the title molecule, C₁₈H₂₀NO₃PS, the benzene ring and the benzothiazole mean plane are almost coplanar, forming a dihedral angle of 2.29 (2)°. The two ethyl groups are each disordered over two conformations in ratios that refined to 0.59 (1):0.41 (1) and 0.56 (1):0.44 (1). In the crystal, weak intermolecular C—H⋯O hydrogen bonds link the molecules into layers parallel to the bc plane.

Related literature

For the cardiovascular activity of benzothiazole-substituted benzylphosphonate derivatives, see: Yoshino et al. (1986 ). For the crystal structure of a related benzothiazole-substituted derivative, see: Bhatia et al. (1991 ).

Experimental

Crystal data

C₁₈H₂₀NO₃PS
M_r = 361.38
Monoclinic, P 2₁ /c
a = 11.0441 (19) Å
b = 8.0927 (14) Å
c = 20.933 (4) Å
β = 94.943 (3)°
V = 1863.9 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.980, T_max = 0.986
11571 measured reflections
3641 independent reflections
2005 reflections with I > 2σ(I)
R_int = 0.104

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.150
S = 0.96
3641 reflections
259 parameters
8 restraints
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1ⁱ	0.93	2.45	3.261 (5)	146
C13—H13⋯O1ⁱⁱ	0.93	2.53	3.310 (4)	141
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x+2, -y+1, -z+2.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 1999 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810047045/cv2793sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810047045/cv2793Isup2.hkl

checkCIF report

Comment top

It was found that benzothiazole-substituted benzylphosphonates derivatives could exhibit excellent cardiovascular activities (Yoshino et al., 1986). We herein report the structure of the diethyl 4-(benzo[d]thiazol-2-yl)benzylphosphonate (I) (Fig. 1).

In (I), the bond lengths and angles are normal and comparable with those observed in the related compound (Bhatia et al., 1991). The benzene ring and the benzothiazole mean plane are almost coplanar forming a dihedral angle of 2.29 (2)°. Weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into layers parallel to bc plane.

Related literature top

For the cardiovascular activity of benzothiazole-substituted benzylphosphonate derivatives, see: Yoshino et al. (1986). For the crystal structure of a related benzothiazole-substituted derivative, see: Bhatia et al. (1991).

Experimental top

The title compound was synthesized according to the method of Yoshino et al. (1986). Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of the solution in hexane-MeOH (3:1).

Structure description top

For the cardiovascular activity of benzothiazole-substituted benzylphosphonate derivatives, see: Yoshino et al. (1986). For the crystal structure of a related benzothiazole-substituted derivative, see: Bhatia et al. (1991).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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 title molecule with the atom-numbering scheme. The displacement ellipsoids are drawn at the 30% probability level.

Diethyl [4-(1,3-benzothiazol-2-yl)benzyl]phosphonate top

Crystal data top

C₁₈H₂₀NO₃PS	F(000) = 760
M_r = 361.38	D_x = 1.288 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1606 reflections
a = 11.0441 (19) Å	θ = 2.6–19.8°
b = 8.0927 (14) Å	µ = 0.27 mm⁻¹
c = 20.933 (4) Å	T = 298 K
β = 94.943 (3)°	Block, yellow
V = 1863.9 (6) Å³	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3641 independent reflections
Radiation source: fine-focus sealed tube	2005 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.104
phi and ω scans	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→13
T_min = 0.980, T_max = 0.986	k = −9→9
11571 measured reflections	l = −25→23

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.0548P)²] where P = (F_o² + 2F_c²)/3
3641 reflections	(Δ/σ)_max = 0.002
259 parameters	Δρ_max = 0.25 e Å⁻³
8 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₈H₂₀NO₃PS	V = 1863.9 (6) Å³
M_r = 361.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.0441 (19) Å	µ = 0.27 mm⁻¹
b = 8.0927 (14) Å	T = 298 K
c = 20.933 (4) Å	0.20 × 0.20 × 0.20 mm
β = 94.943 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3641 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2005 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.986	R_int = 0.104
11571 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	8 restraints
wR(F²) = 0.150	H-atom parameters constrained
S = 0.96	Δρ_max = 0.25 e Å⁻³
3641 reflections	Δρ_min = −0.20 e Å⁻³
259 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 > 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	Occ. (<1)
C1	1.1588 (3)	0.1221 (4)	0.69500 (17)	0.0623 (10)
C2	1.2308 (3)	0.2279 (4)	0.73429 (17)	0.0595 (9)
C3	1.3327 (4)	0.2969 (5)	0.7108 (2)	0.0774 (11)
H3	1.3822	0.3682	0.7363	0.093*
C4	1.3602 (4)	0.2599 (5)	0.6504 (2)	0.0840 (12)
H4	1.4286	0.3074	0.6350	0.101*
C5	1.2893 (4)	0.1538 (5)	0.6113 (2)	0.0865 (12)
H5	1.3103	0.1307	0.5702	0.104*
C6	1.1881 (4)	0.0827 (5)	0.63310 (19)	0.0811 (12)
H6	1.1401	0.0101	0.6074	0.097*
C7	1.0931 (3)	0.1737 (4)	0.80139 (17)	0.0566 (9)
C8	1.0286 (3)	0.1760 (4)	0.85962 (17)	0.0550 (9)
C9	0.9251 (3)	0.0812 (4)	0.86477 (18)	0.0681 (10)
H9	0.8941	0.0177	0.8301	0.082*
C10	0.8674 (3)	0.0802 (4)	0.9212 (2)	0.0705 (10)
H10	0.7980	0.0162	0.9237	0.085*
C11	0.9113 (3)	0.1726 (4)	0.97371 (18)	0.0609 (9)
C12	1.0131 (3)	0.2685 (4)	0.96797 (18)	0.0639 (10)
H12	1.0432	0.3334	1.0024	0.077*
C13	1.0714 (3)	0.2703 (4)	0.91201 (18)	0.0624 (9)
H13	1.1401	0.3356	0.9096	0.075*
C14	0.8502 (3)	0.1645 (5)	1.03566 (18)	0.0743 (11)
H14A	0.9076	0.2020	1.0703	0.089*
H14B	0.8313	0.0499	1.0441	0.089*
C15	0.5008 (10)	0.2379 (17)	0.9677 (8)	0.080 (4)	0.59 (1)
H15A	0.4858	0.3496	0.9819	0.096*	0.59 (1)
H15B	0.4421	0.1645	0.9848	0.096*	0.59 (1)
C16	0.491 (2)	0.229 (3)	0.8963 (9)	0.127 (7)	0.59 (1)
H16A	0.5536	0.2969	0.8803	0.191*	0.59 (1)
H16B	0.4130	0.2690	0.8795	0.191*	0.59 (1)
H16C	0.5015	0.1171	0.8830	0.191*	0.59 (1)
C17	0.6829 (11)	0.3458 (18)	1.1595 (6)	0.081 (4)	0.56 (1)
H17A	0.6131	0.4165	1.1637	0.098*	0.56 (1)
H17B	0.7550	0.4137	1.1582	0.098*	0.56 (1)
C18	0.698 (2)	0.221 (3)	1.2130 (9)	0.102 (7)	0.56 (1)
H18A	0.6202	0.1731	1.2193	0.152*	0.56 (1)
H18B	0.7292	0.2754	1.2518	0.152*	0.56 (1)
H18C	0.7530	0.1365	1.2022	0.152*	0.56 (1)
C15'	0.5313 (16)	0.286 (3)	0.9542 (13)	0.095 (7)	0.41 (1)
H15C	0.5686	0.3679	0.9281	0.114*	0.41 (1)
H15D	0.4836	0.3439	0.9840	0.114*	0.41 (1)
C16'	0.453 (3)	0.175 (4)	0.9131 (15)	0.114 (9)	0.41 (1)
H16D	0.4893	0.1547	0.8738	0.171*	0.41 (1)
H16E	0.3745	0.2248	0.9037	0.171*	0.41 (1)
H16F	0.4436	0.0718	0.9350	0.171*	0.41 (1)
C17'	0.7377 (13)	0.300 (3)	1.1609 (8)	0.084 (5)	0.44 (1)
H17C	0.7514	0.4181	1.1565	0.101*	0.44 (1)
H17D	0.8162	0.2461	1.1638	0.101*	0.44 (1)
C18'	0.679 (3)	0.271 (4)	1.2219 (12)	0.091 (8)	0.44 (1)
H18D	0.5941	0.2968	1.2155	0.137*	0.44 (1)
H18E	0.7169	0.3392	1.2553	0.137*	0.44 (1)
H18F	0.6886	0.1566	1.2340	0.137*	0.44 (1)
N1	1.1913 (2)	0.2556 (3)	0.79452 (14)	0.0638 (8)
O1	0.7282 (2)	0.4580 (3)	1.02534 (11)	0.0758 (7)
O3	0.6649 (2)	0.2406 (3)	1.10323 (12)	0.0780 (8)
O2	0.6244 (2)	0.1867 (3)	0.98898 (12)	0.0767 (8)
P1	0.71450 (8)	0.28288 (12)	1.03709 (5)	0.0610 (3)
S1	1.03702 (9)	0.05586 (12)	0.73533 (5)	0.0754 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.057 (2)	0.065 (2)	0.062 (2)	0.0036 (18)	−0.0136 (18)	−0.0071 (19)
C2	0.049 (2)	0.072 (2)	0.056 (2)	0.0097 (18)	−0.0021 (18)	−0.0063 (19)
C3	0.061 (3)	0.095 (3)	0.075 (3)	0.002 (2)	0.000 (2)	−0.020 (2)
C4	0.066 (3)	0.105 (3)	0.082 (3)	0.012 (2)	0.009 (2)	−0.012 (3)
C5	0.097 (3)	0.096 (3)	0.066 (3)	0.016 (3)	0.005 (3)	−0.009 (2)
C6	0.096 (3)	0.085 (3)	0.058 (3)	0.004 (2)	−0.012 (2)	−0.015 (2)
C7	0.047 (2)	0.055 (2)	0.066 (2)	0.0101 (17)	−0.0098 (18)	−0.0057 (17)
C8	0.0395 (19)	0.055 (2)	0.068 (2)	0.0065 (16)	−0.0079 (17)	−0.0057 (18)
C9	0.058 (2)	0.074 (3)	0.070 (3)	−0.0026 (19)	−0.008 (2)	−0.014 (2)
C10	0.045 (2)	0.077 (3)	0.087 (3)	−0.0060 (18)	−0.006 (2)	0.000 (2)
C11	0.046 (2)	0.067 (2)	0.069 (3)	0.0102 (18)	−0.0033 (19)	0.006 (2)
C12	0.055 (2)	0.069 (2)	0.066 (2)	0.0032 (19)	−0.0060 (19)	−0.0095 (19)
C13	0.048 (2)	0.060 (2)	0.078 (3)	−0.0030 (17)	−0.0071 (19)	−0.007 (2)
C14	0.060 (2)	0.085 (3)	0.076 (3)	0.010 (2)	−0.005 (2)	0.015 (2)
C15	0.038 (6)	0.082 (7)	0.119 (10)	−0.003 (5)	0.000 (6)	−0.027 (7)
C16	0.136 (18)	0.147 (19)	0.090 (9)	0.005 (9)	−0.043 (10)	−0.011 (9)
C17	0.089 (10)	0.092 (8)	0.065 (7)	−0.006 (7)	0.014 (7)	−0.008 (5)
C18	0.111 (11)	0.116 (14)	0.072 (11)	0.034 (8)	−0.022 (9)	0.001 (9)
C15'	0.047 (10)	0.119 (16)	0.117 (17)	−0.015 (8)	−0.010 (10)	−0.007 (10)
C16'	0.081 (14)	0.109 (16)	0.14 (2)	0.002 (10)	−0.043 (14)	−0.013 (14)
C17'	0.067 (11)	0.113 (14)	0.074 (9)	−0.014 (9)	0.016 (8)	−0.021 (9)
C18'	0.088 (13)	0.110 (18)	0.075 (11)	−0.012 (13)	0.005 (8)	−0.016 (10)
N1	0.0427 (18)	0.077 (2)	0.070 (2)	0.0028 (15)	−0.0056 (15)	−0.0137 (16)
O1	0.0827 (18)	0.0666 (16)	0.0759 (17)	−0.0010 (13)	−0.0063 (14)	0.0039 (13)
O3	0.0760 (18)	0.0861 (18)	0.0732 (17)	−0.0192 (13)	0.0138 (14)	−0.0070 (15)
O2	0.0601 (16)	0.0811 (17)	0.0856 (18)	0.0031 (13)	−0.0133 (14)	−0.0165 (14)
P1	0.0519 (6)	0.0678 (7)	0.0622 (6)	−0.0007 (5)	−0.0016 (5)	0.0004 (5)
S1	0.0690 (7)	0.0816 (7)	0.0724 (7)	−0.0100 (5)	−0.0119 (5)	−0.0187 (5)

Geometric parameters (Å, º) top

C1—C2	1.389 (5)	C15—C16	1.492 (15)
C1—C6	1.399 (5)	C15—H15A	0.9700
C1—S1	1.734 (4)	C15—H15B	0.9700
C2—C3	1.384 (5)	C16—H16A	0.9600
C2—N1	1.388 (4)	C16—H16B	0.9600
C3—C4	1.359 (5)	C16—H16C	0.9600
C3—H3	0.9300	C17—O3	1.454 (11)
C4—C5	1.383 (5)	C17—C18	1.504 (16)
C4—H4	0.9300	C17—H17A	0.9700
C5—C6	1.370 (5)	C17—H17B	0.9700
C5—H5	0.9300	C18—H18A	0.9600
C6—H6	0.9300	C18—H18B	0.9600
C7—N1	1.289 (4)	C18—H18C	0.9600
C7—C8	1.464 (5)	C15'—O2	1.452 (16)
C7—S1	1.749 (3)	C15'—C16'	1.477 (18)
C8—C13	1.385 (4)	C15'—H15C	0.9700
C8—C9	1.389 (5)	C15'—H15D	0.9700
C9—C10	1.390 (5)	C16'—H16D	0.9600
C9—H9	0.9300	C16'—H16E	0.9600
C10—C11	1.382 (5)	C16'—H16F	0.9600
C10—H10	0.9300	C17'—O3	1.474 (14)
C11—C12	1.380 (5)	C17'—C18'	1.501 (17)
C11—C14	1.514 (5)	C17'—H17C	0.9700
C12—C13	1.385 (5)	C17'—H17D	0.9700
C12—H12	0.9300	C18'—H18D	0.9600
C13—H13	0.9300	C18'—H18E	0.9600
C14—P1	1.781 (3)	C18'—H18F	0.9600
C14—H14A	0.9700	O1—P1	1.448 (2)
C14—H14B	0.9700	O3—P1	1.570 (3)
C15—O2	1.459 (11)	O2—P1	1.561 (2)

C2—C1—C6	121.5 (4)	O2—C15—H15B	110.5
C2—C1—S1	109.3 (3)	C16—C15—H15B	110.5
C6—C1—S1	129.2 (3)	H15A—C15—H15B	108.7
C3—C2—N1	125.9 (3)	O3—C17—C18	102.1 (13)
C3—C2—C1	118.7 (4)	O3—C17—H17A	111.3
N1—C2—C1	115.4 (3)	C18—C17—H17A	111.3
C4—C3—C2	119.7 (4)	O3—C17—H17B	111.3
C4—C3—H3	120.2	C18—C17—H17B	111.3
C2—C3—H3	120.2	H17A—C17—H17B	109.2
C3—C4—C5	121.8 (4)	O2—C15'—C16'	107.9 (19)
C3—C4—H4	119.1	O2—C15'—H15C	110.1
C5—C4—H4	119.1	C16'—C15'—H15C	110.1
C6—C5—C4	120.0 (4)	O2—C15'—H15D	110.1
C6—C5—H5	120.0	C16'—C15'—H15D	110.1
C4—C5—H5	120.0	H15C—C15'—H15D	108.4
C5—C6—C1	118.2 (4)	C15'—C16'—H16D	109.5
C5—C6—H6	120.9	C15'—C16'—H16E	109.5
C1—C6—H6	120.9	H16D—C16'—H16E	109.5
N1—C7—C8	124.1 (3)	C15'—C16'—H16F	109.5
N1—C7—S1	115.8 (3)	H16D—C16'—H16F	109.5
C8—C7—S1	120.0 (3)	H16E—C16'—H16F	109.5
C13—C8—C9	118.0 (4)	O3—C17'—C18'	113.6 (17)
C13—C8—C7	120.6 (3)	O3—C17'—H17C	108.8
C9—C8—C7	121.4 (3)	C18'—C17'—H17C	108.8
C8—C9—C10	120.7 (3)	O3—C17'—H17D	108.8
C8—C9—H9	119.7	C18'—C17'—H17D	108.9
C10—C9—H9	119.7	H17C—C17'—H17D	107.7
C11—C10—C9	121.2 (3)	C17'—C18'—H18D	109.5
C11—C10—H10	119.4	C17'—C18'—H18E	109.5
C9—C10—H10	119.4	H18D—C18'—H18E	109.5
C12—C11—C10	117.9 (4)	C17'—C18'—H18F	109.5
C12—C11—C14	121.7 (3)	H18D—C18'—H18F	109.5
C10—C11—C14	120.4 (3)	H18E—C18'—H18F	109.5
C11—C12—C13	121.4 (3)	C7—N1—C2	110.6 (3)
C11—C12—H12	119.3	C17—O3—C17'	27.9 (6)
C13—C12—H12	119.3	C17—O3—P1	123.6 (7)
C12—C13—C8	120.8 (3)	C17'—O3—P1	116.4 (8)
C12—C13—H13	119.6	C15'—O2—C15	23.9 (10)
C8—C13—H13	119.6	C15'—O2—P1	115.5 (10)
C11—C14—P1	115.4 (2)	C15—O2—P1	125.6 (7)
C11—C14—H14A	108.4	O1—P1—O2	116.64 (14)
P1—C14—H14A	108.4	O1—P1—O3	114.38 (15)
C11—C14—H14B	108.4	O2—P1—O3	102.06 (14)
P1—C14—H14B	108.4	O1—P1—C14	115.01 (17)
H14A—C14—H14B	107.5	O2—P1—C14	102.21 (16)
O2—C15—C16	106.0 (13)	O3—P1—C14	104.79 (16)
O2—C15—H15A	110.5	C1—S1—C7	88.84 (18)
C16—C15—H15A	110.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.93	2.45	3.261 (5)	146
C13—H13···O1ⁱⁱ	0.93	2.53	3.310 (4)	141

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

Experimental details

Crystal data
Chemical formula	C₁₈H₂₀NO₃PS
M_r	361.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	11.0441 (19), 8.0927 (14), 20.933 (4)
β (°)	94.943 (3)
V (Å³)	1863.9 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.980, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	11571, 3641, 2005
R_int	0.104
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.150, 0.96
No. of reflections	3641
No. of parameters	259
No. of restraints	8
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.20

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 1999), 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
C5—H5···O1ⁱ	0.93	2.45	3.261 (5)	146
C13—H13···O1ⁱⁱ	0.93	2.53	3.310 (4)	141

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

Acknowledgements

The authors are grateful to Xiangfan University for financial support.

References

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Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. 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
Yoshino, K., Kohno, T., Uno, T., Morita, T. & Tsukamoto, G. (1986). J. Med. Chem. 29, 820–825. CrossRef CAS PubMed Web of Science Google Scholar