5-(2-Meth­oxy­phen­yl)-1,3,4-thia­diazol-2-yl 2-meth­oxy­benzoate hemihydrate

Yao, J.; Guo, B.; An, K.; Guan, J.

doi:10.1107/S1600536811010373

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1046

doi:10.1107/S1600536811010373

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5-(2-Methoxyphenyl)-1,3,4-thiadiazol-2-yl 2-methoxybenzoate hemihydrate

Jin-hua Yao,^a Bing Guo,^a Kang An ^a and Jian-ning Guan ^a ^*

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, No.5 Xinmofan Road, Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: guanjn@sina.com

(Received 24 February 2011; accepted 19 March 2011; online 7 April 2011)

In the title compound, C₁₇H₁₄N₂O₄S·0.5H₂O, the molecule, with the exception of the two methoxyphenyl groups, is nearly planar with an r.m.s. deviation of 0.0305 Å. The two 2-methoxyphenyl rings make dihedral angles of 4.1 (3) and 2.3 (3)° with the thiadiazole ring. In the crystal, intermolecular C—H⋯O and O—H⋯N hydrogen bonds link the molecules.

Related literature

For general background to 1,3,4-thiadiazole derivatives, see: Matysiak & Opolski (2006 ). Alireza et al. (2005 ). Wang et al. (1999 ). For bond-length data, see: Allen et al. (1987 ). For the synthesis, see: Kurzer (1971 ).

Experimental

Crystal data

C₁₇H₁₄N₂O₄S·0.5H₂O
M_r = 356.37
Monoclinic, C 2/c
a = 29.858 (6) Å
b = 14.542 (3) Å
c = 7.6710 (15) Å
β = 95.19 (3)°
V = 3317.1 (12) Å³
Z = 8
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.936, T_max = 0.978
3108 measured reflections
3050 independent reflections
1881 reflections with I > 2σ(I)
R_int = 0.025
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.176
S = 1.00
3050 reflections
228 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯N2ⁱ	1.05 (9)	1.81 (9)	2.821 (4)	159 (7)
C11—H11⋯O3ⁱⁱ	0.93	2.50	3.324 (4)	148
Symmetry codes: (i) x, y, z-1; (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+3]$ .

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811010373/bq2283sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811010373/bq2283Isup2.hkl

checkCIF report

Comment top

1,3,4-Thiadiazole derivatives are of great interest because of their chemical and pharmaceutical properties. Some derivatives play a key role in preparing intermediate for anticarcinogen. Recently new derivatives with 1,3,4-thiadiazole nucleus have been synthesized and evaluated for their antiproliferative effect in vitro against the cells of various human tumor cell lines (Matysiak & Opolski, 2006). Some derivatives have effective antibacterial activity. They are of great potential value for killing bacteria (Alireza et al. 2005). In addition, this kind of compounds are known to exhibit diverse biological effects, such as insecticidal activity (Wang et al. 1999).

Herein we report on the crystal structure of the titled compound, (I). The molecular structure of (I) is shown in Fig. 1. The bond lengths (Allen et al. 1987) and angles are within normal ranges. In this structure, there are three rings, ring A (C1/C2/C3/C4/C5/C6), ring B (N1/C7/S/C8/N2) and ring C (C10/C11/C12/C13/C14/C15), all of which are almost planar. Ring B(N1/C7/S/C8/N2) is a planar five-membered ring and the mean deviation from plane is 0.0020 Å. The dihedral angle between ring A and ring B is 4.1 (3)°, ring B and ring C is 2.3 (3)°. In the crystal structure, intermolecular C11—H11···O3 and O1W—H1W···N2 hydrogen bonds (Table 1.) link the molecules to form network structure (Fig. 2), in which they may be effective for the stabilization of the structure.

Related literature top

For general background to 1,3,4-thiadiazole derivatives, see: Matysiak & Opolski (2006). Alireza et al. (2005). Wang et al. (1999). For bond-length data, see: Allen et al. (1987). For the synthesis, see: Kurzer (1971).

Experimental top

3-Methoxy-phthalic anhydride(8 mmol) and 2-(2-methoxyphenyl)-5-hydroxy-1,3,4-thiadiazol(8 mmol) were added in ethanol(50 ml) (Kurzer, 1971). The mixture was refluxed for 5 h. Reactions were monitored by thin-layer chromatography (TLC) with visualization by ultraviolet light and then the solvent was totally evaporated. Then the white power was obtained. The solid was recrystallized from tetrahydrofuran to give the compound (I) (m.p. 520 K). Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a mixed solution of chloroform and tetrahydrofuran.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); 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: SHELXS97 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the molecular structure of (I). Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram for (I). Dashed lines indicate intermolecular C—H···O and O—H···N hydrogen bonds.

5-(2-Methoxyphenyl)-1,3,4-thiadiazol-2-yl 2-methoxybenzoate hemihydrate top

Crystal data top

C₁₇H₁₄N₂O₄S·0.5H₂O	F(000) = 1464
M_r = 356.37	D_x = 1.407 Mg m⁻³
Monoclinic, C2/c	Melting point: 520 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 29.858 (6) Å	Cell parameters from 25 reflections
b = 14.542 (3) Å	θ = 9–13°
c = 7.6710 (15) Å	µ = 0.22 mm⁻¹
β = 95.19 (3)°	T = 293 K
V = 3317.1 (12) Å³	Block, colorless
Z = 8	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1881 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.025
Graphite monochromator	θ_max = 25.4°, θ_min = 1.4°
ω/2θ scans	h = 0→35
Absorption correction: ψ scan (North et al., 1968)	k = 0→17
T_min = 0.936, T_max = 0.978	l = −9→9
3108 measured reflections	3 standard reflections every 200 reflections
3050 independent reflections	intensity decay: 1%

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.176	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.098P)²] where P = (F_o² + 2F_c²)/3
3050 reflections	(Δ/σ)_max = 0.001
228 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₇H₁₄N₂O₄S·0.5H₂O	V = 3317.1 (12) Å³
M_r = 356.37	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 29.858 (6) Å	µ = 0.22 mm⁻¹
b = 14.542 (3) Å	T = 293 K
c = 7.6710 (15) Å	0.30 × 0.20 × 0.10 mm
β = 95.19 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1881 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.025
T_min = 0.936, T_max = 0.978	3 standard reflections every 200 reflections
3108 measured reflections	intensity decay: 1%
3050 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.176	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.41 e Å⁻³
3050 reflections	Δρ_min = −0.28 e Å⁻³
228 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
C1	0.05152 (13)	0.3419 (3)	0.6081 (4)	0.0711 (11)
H1	0.0270	0.3110	0.6471	0.085*
C2	0.04737 (17)	0.3882 (4)	0.4474 (5)	0.0932 (16)
H2	0.0195	0.3907	0.3827	0.112*
C3	0.08311 (19)	0.4293 (3)	0.3852 (5)	0.0898 (14)
H3	0.0800	0.4570	0.2755	0.108*
C4	0.12303 (15)	0.4305 (3)	0.4795 (4)	0.0698 (11)
H4	0.1472	0.4607	0.4363	0.084*
C5	0.12879 (12)	0.3875 (2)	0.6401 (4)	0.0525 (9)
C6	0.09271 (11)	0.3426 (2)	0.7089 (4)	0.0490 (8)
C7	0.09536 (10)	0.2968 (2)	0.8806 (4)	0.0441 (7)
C8	0.10712 (11)	0.2309 (3)	1.1613 (5)	0.0540 (9)
C9	0.16054 (10)	0.2020 (2)	1.4126 (4)	0.0438 (7)
C10	0.16644 (9)	0.1570 (2)	1.5889 (3)	0.0385 (7)
C11	0.20815 (11)	0.1655 (2)	1.6793 (4)	0.0527 (8)
H11	0.2302	0.1989	1.6288	0.063*
C12	0.21841 (13)	0.1272 (3)	1.8389 (5)	0.0630 (10)
H12	0.2469	0.1350	1.8966	0.076*
C13	0.18718 (14)	0.0778 (3)	1.9137 (5)	0.0707 (11)
H13	0.1945	0.0503	2.0220	0.085*
C14	0.14490 (13)	0.0674 (2)	1.8324 (4)	0.0597 (10)
H14	0.1235	0.0336	1.8861	0.072*
C15	0.13365 (10)	0.1075 (2)	1.6690 (4)	0.0419 (7)
C16	0.20649 (14)	0.4248 (3)	0.6754 (6)	0.1006 (16)
H16A	0.2114	0.3935	0.5687	0.151*
H16B	0.2323	0.4173	0.7582	0.151*
H16C	0.2017	0.4891	0.6517	0.151*
C17	0.05776 (12)	0.0530 (3)	1.6602 (5)	0.0806 (13)
H17A	0.0673	−0.0086	1.6895	0.121*
H17B	0.0310	0.0510	1.5811	0.121*
H17C	0.0517	0.0851	1.7649	0.121*
N1	0.06100 (9)	0.2548 (2)	0.9303 (3)	0.0558 (8)
N2	0.06703 (10)	0.2169 (2)	1.0882 (4)	0.0720 (9)
O1	0.16829 (8)	0.38751 (17)	0.7453 (3)	0.0615 (7)
O2	0.11766 (6)	0.19761 (15)	1.3039 (3)	0.0518 (6)
O3	0.19112 (7)	0.24147 (19)	1.3498 (3)	0.0691 (8)
O4	0.09264 (7)	0.10003 (17)	1.5783 (3)	0.0561 (6)
S	0.14064 (3)	0.29401 (7)	1.03358 (11)	0.0554 (3)
O1W	0.0000	0.1206 (3)	0.2500	0.1159 (19)
H1W	0.019 (3)	0.159 (6)	0.167 (12)	0.40 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.073 (3)	0.091 (3)	0.048 (2)	0.003 (2)	0.0013 (19)	0.009 (2)
C2	0.102 (4)	0.126 (4)	0.048 (2)	0.029 (3)	−0.017 (2)	0.006 (3)
C3	0.134 (4)	0.093 (4)	0.043 (2)	0.019 (3)	0.009 (3)	0.021 (2)
C4	0.120 (3)	0.055 (2)	0.0386 (19)	−0.004 (2)	0.028 (2)	0.0050 (17)
C5	0.077 (2)	0.045 (2)	0.0388 (17)	−0.0061 (17)	0.0212 (17)	0.0022 (15)
C6	0.058 (2)	0.058 (2)	0.0316 (15)	−0.0035 (16)	0.0110 (14)	0.0026 (15)
C7	0.0462 (17)	0.0501 (19)	0.0380 (16)	−0.0056 (15)	0.0142 (13)	0.0003 (14)
C8	0.0469 (19)	0.061 (2)	0.056 (2)	−0.0099 (17)	0.0134 (16)	−0.0026 (18)
C9	0.0421 (16)	0.0516 (19)	0.0399 (16)	−0.0055 (15)	0.0158 (13)	0.0057 (15)
C10	0.0419 (16)	0.0449 (18)	0.0302 (14)	−0.0043 (14)	0.0117 (12)	0.0022 (13)
C11	0.0518 (19)	0.063 (2)	0.0444 (18)	0.0056 (17)	0.0107 (15)	0.0064 (16)
C12	0.060 (2)	0.075 (3)	0.053 (2)	0.014 (2)	−0.0012 (18)	0.0072 (19)
C13	0.094 (3)	0.069 (3)	0.048 (2)	0.013 (2)	−0.001 (2)	0.0129 (19)
C14	0.087 (3)	0.052 (2)	0.0433 (18)	−0.007 (2)	0.0264 (19)	0.0063 (16)
C15	0.0541 (17)	0.0398 (17)	0.0337 (15)	0.0006 (15)	0.0149 (14)	−0.0012 (13)
C16	0.099 (3)	0.110 (4)	0.100 (3)	−0.052 (3)	0.049 (3)	−0.003 (3)
C17	0.071 (2)	0.099 (3)	0.077 (3)	−0.038 (2)	0.031 (2)	−0.006 (2)
N1	0.0557 (17)	0.074 (2)	0.0391 (15)	−0.0111 (15)	0.0085 (13)	0.0099 (14)
N2	0.068 (2)	0.090 (3)	0.0583 (19)	−0.0133 (19)	0.0061 (16)	0.0060 (18)
O1	0.0687 (16)	0.0657 (17)	0.0538 (14)	−0.0200 (13)	0.0250 (13)	0.0021 (12)
O2	0.0355 (11)	0.0463 (13)	0.0756 (16)	−0.0102 (10)	0.0167 (11)	−0.0032 (12)
O3	0.0611 (15)	0.100 (2)	0.0479 (14)	−0.0212 (14)	0.0167 (11)	0.0271 (13)
O4	0.0523 (13)	0.0682 (16)	0.0502 (13)	−0.0190 (12)	0.0183 (11)	0.0020 (11)
S	0.0537 (5)	0.0621 (6)	0.0523 (5)	−0.0108 (4)	0.0158 (4)	0.0026 (4)
O1W	0.083 (3)	0.086 (3)	0.187 (6)	0.000	0.060 (3)	0.000

Geometric parameters (Å, º) top

C1—C6	1.392 (5)	C10—C15	1.401 (4)
C1—C2	1.401 (5)	C11—C12	1.355 (4)
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.347 (6)	C12—C13	1.346 (5)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.338 (5)	C13—C14	1.365 (5)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.378 (5)	C14—C15	1.396 (4)
C4—H4	0.9300	C14—H14	0.9300
C5—O1	1.367 (4)	C15—O4	1.357 (4)
C5—C6	1.403 (4)	C16—O1	1.412 (4)
C6—C7	1.472 (4)	C16—H16A	0.9600
C7—N1	1.282 (4)	C16—H16B	0.9600
C7—S	1.709 (3)	C16—H16C	0.9600
C8—O2	1.212 (4)	C17—O4	1.437 (4)
C8—N2	1.291 (4)	C17—H17A	0.9600
C8—S	1.726 (4)	C17—H17B	0.9600
C9—O3	1.214 (3)	C17—H17C	0.9600
C9—O2	1.465 (4)	N1—N2	1.328 (4)
C9—C10	1.499 (4)	O1W—H1W	1.05 (8)
C10—C11	1.375 (4)

C6—C1—C2	119.2 (4)	C10—C11—H11	118.7
C6—C1—H1	120.4	C13—C12—C11	119.7 (4)
C2—C1—H1	120.4	C13—C12—H12	120.1
C3—C2—C1	121.0 (4)	C11—C12—H12	120.1
C3—C2—H2	119.5	C12—C13—C14	120.8 (3)
C1—C2—H2	119.5	C12—C13—H13	119.6
C4—C3—C2	120.7 (4)	C14—C13—H13	119.6
C4—C3—H3	119.7	C13—C14—C15	120.1 (3)
C2—C3—H3	119.7	C13—C14—H14	119.9
C3—C4—C5	120.7 (4)	C15—C14—H14	119.9
C3—C4—H4	119.6	O4—C15—C14	124.1 (3)
C5—C4—H4	119.6	O4—C15—C10	116.8 (3)
O1—C5—C4	124.0 (3)	C14—C15—C10	119.2 (3)
O1—C5—C6	115.4 (3)	O1—C16—H16A	109.5
C4—C5—C6	120.6 (4)	O1—C16—H16B	109.5
C1—C6—C5	117.7 (3)	H16A—C16—H16B	109.5
C1—C6—C7	117.8 (3)	O1—C16—H16C	109.5
C5—C6—C7	124.5 (3)	H16A—C16—H16C	109.5
N1—C7—C6	120.2 (3)	H16B—C16—H16C	109.5
N1—C7—S	112.9 (2)	O4—C17—H17A	109.5
C6—C7—S	126.9 (2)	O4—C17—H17B	109.5
O2—C8—N2	118.9 (3)	H17A—C17—H17B	109.5
O2—C8—S	127.5 (3)	O4—C17—H17C	109.5
N2—C8—S	113.6 (3)	H17A—C17—H17C	109.5
O3—C9—O2	116.4 (3)	H17B—C17—H17C	109.5
O3—C9—C10	122.2 (3)	C7—N1—N2	115.0 (3)
O2—C9—C10	121.3 (2)	C8—N2—N1	112.0 (3)
C11—C10—C15	117.5 (3)	C5—O1—C16	117.3 (3)
C11—C10—C9	116.3 (3)	C8—O2—C9	129.7 (3)
C15—C10—C9	126.2 (3)	C15—O4—C17	118.0 (3)
C12—C11—C10	122.6 (3)	C7—S—C8	86.50 (16)
C12—C11—H11	118.7

C6—C1—C2—C3	3.4 (7)	C13—C14—C15—O4	179.4 (3)
C1—C2—C3—C4	−3.2 (8)	C13—C14—C15—C10	0.9 (5)
C2—C3—C4—C5	1.9 (7)	C11—C10—C15—O4	179.8 (3)
C3—C4—C5—O1	−178.6 (4)	C9—C10—C15—O4	−0.4 (4)
C3—C4—C5—C6	−0.8 (6)	C11—C10—C15—C14	−1.6 (4)
C2—C1—C6—C5	−2.3 (5)	C9—C10—C15—C14	178.2 (3)
C2—C1—C6—C7	177.3 (3)	C6—C7—N1—N2	−179.3 (3)
O1—C5—C6—C1	179.0 (3)	S—C7—N1—N2	−0.5 (4)
C4—C5—C6—C1	1.0 (5)	O2—C8—N2—N1	−177.8 (3)
O1—C5—C6—C7	−0.5 (5)	S—C8—N2—N1	−0.1 (4)
C4—C5—C6—C7	−178.4 (3)	C7—N1—N2—C8	0.4 (5)
C1—C6—C7—N1	2.8 (5)	C4—C5—O1—C16	−7.5 (5)
C5—C6—C7—N1	−177.7 (3)	C6—C5—O1—C16	174.6 (3)
C1—C6—C7—S	−175.8 (3)	N2—C8—O2—C9	179.1 (3)
C5—C6—C7—S	3.7 (5)	S—C8—O2—C9	1.8 (5)
O3—C9—C10—C11	2.2 (5)	O3—C9—O2—C8	−3.4 (5)
O2—C9—C10—C11	179.9 (3)	C10—C9—O2—C8	178.8 (3)
O3—C9—C10—C15	−177.7 (3)	C14—C15—O4—C17	4.1 (5)
O2—C9—C10—C15	0.1 (5)	C10—C15—O4—C17	−177.4 (3)
C15—C10—C11—C12	0.9 (5)	N1—C7—S—C8	0.4 (3)
C9—C10—C11—C12	−179.0 (3)	C6—C7—S—C8	179.1 (3)
C10—C11—C12—C13	0.7 (6)	O2—C8—S—C7	177.3 (4)
C11—C12—C13—C14	−1.4 (6)	N2—C8—S—C7	−0.2 (3)
C12—C13—C14—C15	0.7 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···N2ⁱ	1.05 (9)	1.81 (9)	2.821 (4)	159 (7)
C11—H11···O3ⁱⁱ	0.93	2.50	3.324 (4)	148

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄N₂O₄S·0.5H₂O
M_r	356.37
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	29.858 (6), 14.542 (3), 7.6710 (15)
β (°)	95.19 (3)
V (Å³)	3317.1 (12)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.936, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	3108, 3050, 1881
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.176, 1.00
No. of reflections	3050
No. of parameters	228
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.28

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), 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
O1W—H1W···N2ⁱ	1.05 (9)	1.81 (9)	2.821 (4)	159 (7)
C11—H11···O3ⁱⁱ	0.93	2.50	3.324 (4)	148

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

Acknowledgements

The authors would like to thank Professor Hua-qin Wang of Nanjing University, for carrying out the X-ray crystallographic analysis.

References

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