2-Meth­oxy-N-[5-(2-methoxy­phen­yl)-1,3,4-thia­diazol-2-yl]benzamide hemi­hydrate

Yin, L.; Wan, R.; Han, F.; Wang, B.; Wang, J.

doi:10.1107/S1600536808019934

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1637

doi:10.1107/S1600536808019934

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2-Methoxy-N-[5-(2-methoxyphenyl)-1,3,4-thiadiazol-2-yl]benzamide hemihydrate

Li-he Yin,^a Rong Wan,^a ^* Feng Han,^a Bin Wang ^a and Jin-tang Wang ^a

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

(Received 27 June 2008; accepted 30 June 2008; online 31 July 2008)

In the molecule of the title compound, C₁₇H₁₅N₃O₃S·0.5H₂O, the thiadiazole ring is oriented with respect to the two 2-methoxyphenyl rings at dihedral angles of 3.70 (3) and 1.74 (2)°. An intramolecular N—H⋯O hydrogen bond results in the formation of a planar six-membered ring, which is oriented with respect to the thiadiazole ring at a dihedral angle of 1.33 (3)°. Thus, all of the rings are nearly coplanar. In the crystal structure, intermolecular O—H⋯N and C—H⋯O hydrogen bonds link the molecules.

Related literature

For related literature, see: Nakagawa et al. (1996 ); Wang et al. (1999 ).

Experimental

Crystal data

C₁₇H₁₅N₃O₃S·0.5H₂O
M_r = 350.40
Monoclinic, C 2/c
a = 29.950 (6) Å
b = 14.561 (3) Å
c = 7.6520 (15) Å
β = 94.78 (3)°
V = 3325.4 (12) Å³
Z = 8
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 298 (2) K
0.30 × 0.10 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.937, T_max = 0.989
6340 measured reflections
3003 independent reflections
1602 reflections with I > 2σ(I)
R_int = 0.060
3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.079
wR(F²) = 0.240
S = 1.04
3003 reflections
222 parameters
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O3	0.86	2.04	2.706 (5)	134
O4—H4⋯N1ⁱ	0.85	2.24	2.796 (6)	123
C14—H14A⋯O2ⁱⁱ	0.93	2.49	3.316 (6)	148
Symmetry codes: (i) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); 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: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808019934/hk2483sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808019934/hk2483Isup2.hkl

checkCIF report

Comment top

1,3,4-Thiadiazole derivatives represent an interesting class of compounds possessing broad spectrum biological activities (Nakagawa et al., 1996; Wang et al., 1999). These compounds are known to exhibit diverse biological effects, such as insecticidal and fungicidal activities (Wang et al., 1999). We report herein the crystal structure of the title compound.

In the molecule of the title compound (Fig. 1) the bond lengths and angles are within normal ranges. Rings A (C2-C7), B (S/N1/N2/C8/C9) and C (C12-C17) are, of course, planar. The intramolecular N-H···O hydrogen bond (Table 1) results in the formation of a six-membered planar ring D (N3/H3A/O3/C10/C12/C13). The dihedral angles between the rings are A/B = 3.70 (3)°, A/C = 2.81 (3)°, A/D = 2.45 (3)°, B/C = 1.74 (2)°, B/D = 1.33 (3)° and C/D = 0.90 (3)°. So, all of the rings are nearly coplanar.

In the crystal structure, intermolecular O-H···N and C-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: Nakagawa et al. (1996); Wang et al. (1999).

Experimental top

For preparation of the title compound, a solution of 5-(2-methoxyphenyl) -1,3,4-thiadiazol-2-amine (5 mmol) in pyridine (50 ml) was cooled to 273 K. To this solution, 2-methoxybenzoyl chloride (5 mmol) was added via a drop funnel over period of 30 min. The mixture was stirred at 273 K for 1 h, raised to room temperature and reacted for 1 h. The pyridine was distilled and the solid residue was recrystallized from ethanol to give the title compound (m.p. 513-514 K). Crystals suitable for X-ray analysis were obtained by slow evaporation of an acetone solution.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); 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: PLATON (Spek, 2003); 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. Hydrogen bonds are shown as dashed lines.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

2-Methoxy-N-[5-(2-methoxyphenyl)-1,3,4-thiadiazol-2-yl]benzamide hemihydrate top

Crystal data top

C₁₇H₁₅N₃O₃S·0.5H₂O	F(000) = 1464
M_r = 350.40	D_x = 1.400 Mg m⁻³
Monoclinic, C2/c	Melting point = 513–514 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 29.950 (6) Å	Cell parameters from 25 reflections
b = 14.561 (3) Å	θ = 9–12°
c = 7.6520 (15) Å	µ = 0.22 mm⁻¹
β = 94.78 (3)°	T = 298 K
V = 3325.4 (12) Å³	Block, colorless
Z = 8	0.30 × 0.10 × 0.05 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1602 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.061
Graphite monochromator	θ_max = 25.2°, θ_min = 1.4°
ω/2θ scans	h = −35→35
Absorption correction: ψ scan (North et al., 1968)	k = 0→17
T_min = 0.937, T_max = 0.989	l = 0→9
6340 measured reflections	3 standard reflections every 120 min
3003 independent reflections	intensity decay: none

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)] = 0.079	H-atom parameters constrained
wR(F²) = 0.241	w = 1/[σ²(F_o²) + (0.1018P)² + 4.918P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3003 reflections	Δρ_max = 0.57 e Å⁻³
222 parameters	Δρ_min = −0.33 e Å⁻³
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₇H₁₅N₃O₃S·0.5H₂O	V = 3325.4 (12) Å³
M_r = 350.40	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 29.950 (6) Å	µ = 0.22 mm⁻¹
b = 14.561 (3) Å	T = 298 K
c = 7.6520 (15) Å	0.30 × 0.10 × 0.05 mm
β = 94.78 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1602 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.061
T_min = 0.937, T_max = 0.989	3 standard reflections every 120 min
6340 measured reflections	intensity decay: none
3003 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.079	222 parameters
wR(F²) = 0.241	H-atom parameters constrained
S = 1.04	Δρ_max = 0.57 e Å⁻³
3003 reflections	Δρ_min = −0.33 e Å⁻³

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
S	0.14065 (4)	0.20610 (9)	0.03340 (17)	0.0643 (5)
O1	0.16810 (11)	0.1136 (2)	−0.2572 (5)	0.0694 (10)
O2	0.19106 (10)	0.2584 (3)	0.3483 (5)	0.0761 (11)
O3	0.09246 (10)	0.3994 (2)	0.5803 (4)	0.0623 (9)
O4	1.0000	0.3791 (4)	0.2500	0.139 (3)
H4	0.9969	0.3526	0.3472	0.167*
N1	0.06625 (14)	0.2824 (4)	0.0904 (6)	0.0805 (14)
N2	0.06140 (12)	0.2445 (3)	−0.0693 (5)	0.0622 (11)
N3	0.11780 (9)	0.3022 (2)	0.3039 (5)	0.0430 (8)
H3A	0.0969	0.3324	0.3490	0.052*
C1	0.20716 (19)	0.0758 (5)	−0.3250 (9)	0.105 (2)
H1B	0.2323	0.0820	−0.2392	0.157*
H1C	0.2132	0.1081	−0.4299	0.157*
H1D	0.2022	0.0120	−0.3516	0.157*
C2	0.12874 (16)	0.1123 (3)	−0.3594 (6)	0.0575 (12)
C3	0.09255 (15)	0.1571 (3)	−0.2910 (6)	0.0543 (11)
C4	0.05153 (18)	0.1584 (4)	−0.3904 (7)	0.0796 (16)
H4A	0.0273	0.1894	−0.3501	0.095*
C5	0.0471 (2)	0.1124 (5)	−0.5522 (8)	0.0946 (19)
H5A	0.0194	0.1107	−0.6165	0.114*
C6	0.0828 (2)	0.0707 (5)	−0.6157 (8)	0.0954 (19)
H6A	0.0794	0.0422	−0.7248	0.115*
C7	0.1229 (2)	0.0696 (4)	−0.5235 (7)	0.0742 (15)
H7A	0.1470	0.0403	−0.5690	0.089*
C8	0.09539 (14)	0.2027 (3)	−0.1186 (6)	0.0515 (11)
C9	0.10742 (16)	0.2703 (4)	0.1660 (8)	0.0652 (14)
C10	0.16044 (14)	0.2990 (3)	0.4122 (6)	0.0509 (11)
C11	0.05722 (17)	0.4453 (4)	0.6622 (8)	0.0873 (19)
H11A	0.0303	0.4444	0.5846	0.131*
H11B	0.0658	0.5077	0.6873	0.131*
H11C	0.0520	0.4143	0.7694	0.131*
C12	0.13322 (14)	0.3932 (3)	0.6683 (6)	0.0486 (10)
C13	0.16640 (13)	0.3438 (3)	0.5879 (5)	0.0467 (10)
C14	0.20858 (15)	0.3341 (3)	0.6785 (6)	0.0599 (12)
H14A	0.2305	0.3006	0.6276	0.072*
C15	0.21853 (18)	0.3729 (4)	0.8408 (7)	0.0683 (14)
H15A	0.2467	0.3653	0.9000	0.082*
C16	0.1862 (2)	0.4227 (4)	0.9133 (7)	0.0790 (17)
H16A	0.1934	0.4515	1.0205	0.095*
C17	0.14394 (18)	0.4321 (3)	0.8354 (7)	0.0653 (13)
H17A	0.1223	0.4639	0.8917	0.078*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0561 (8)	0.0660 (8)	0.0708 (8)	0.0122 (6)	0.0047 (6)	−0.0030 (7)
O1	0.064 (2)	0.077 (2)	0.069 (2)	0.0236 (17)	0.0142 (18)	−0.0027 (19)
O2	0.0527 (19)	0.107 (3)	0.068 (2)	0.0223 (19)	0.0017 (16)	−0.028 (2)
O3	0.0505 (18)	0.070 (2)	0.067 (2)	0.0199 (15)	0.0081 (16)	−0.0046 (18)
O4	0.095 (5)	0.093 (5)	0.239 (10)	0.000	0.060 (5)	0.000
N1	0.069 (3)	0.105 (4)	0.067 (3)	0.022 (3)	0.006 (2)	−0.011 (3)
N2	0.051 (2)	0.087 (3)	0.047 (2)	0.018 (2)	−0.0025 (17)	−0.011 (2)
N3	0.0212 (15)	0.0347 (18)	0.074 (2)	0.0118 (13)	0.0067 (16)	−0.0007 (18)
C1	0.091 (4)	0.124 (5)	0.104 (5)	0.055 (4)	0.040 (4)	0.011 (4)
C2	0.071 (3)	0.047 (3)	0.054 (3)	0.002 (2)	0.004 (2)	0.000 (2)
C3	0.060 (3)	0.055 (3)	0.048 (2)	−0.003 (2)	0.001 (2)	−0.003 (2)
C4	0.067 (3)	0.102 (4)	0.066 (3)	−0.004 (3)	−0.014 (3)	−0.004 (3)
C5	0.096 (4)	0.122 (5)	0.062 (3)	−0.019 (4)	−0.021 (3)	−0.015 (3)
C6	0.129 (5)	0.088 (4)	0.067 (4)	−0.011 (4)	−0.006 (3)	−0.016 (3)
C7	0.106 (4)	0.058 (3)	0.060 (3)	0.008 (3)	0.016 (3)	−0.011 (3)
C8	0.054 (3)	0.048 (3)	0.052 (2)	0.003 (2)	0.003 (2)	0.000 (2)
C9	0.054 (3)	0.069 (3)	0.073 (3)	0.015 (3)	0.013 (3)	0.015 (3)
C10	0.047 (2)	0.049 (3)	0.055 (3)	0.006 (2)	−0.003 (2)	0.003 (2)
C11	0.070 (3)	0.101 (5)	0.095 (4)	0.042 (3)	0.025 (3)	0.002 (4)
C12	0.050 (2)	0.044 (2)	0.051 (2)	0.0060 (19)	0.006 (2)	0.004 (2)
C13	0.045 (2)	0.048 (2)	0.046 (2)	−0.0029 (19)	0.0030 (19)	−0.004 (2)
C14	0.045 (2)	0.067 (3)	0.067 (3)	−0.001 (2)	0.002 (2)	−0.003 (3)
C15	0.069 (3)	0.074 (4)	0.059 (3)	−0.011 (3)	−0.012 (3)	−0.004 (3)
C16	0.102 (4)	0.064 (3)	0.067 (3)	−0.014 (3)	−0.021 (3)	−0.009 (3)
C17	0.084 (3)	0.059 (3)	0.055 (3)	0.004 (3)	0.020 (3)	−0.009 (2)

Geometric parameters (Å, º) top

S—C8	1.712 (4)	C4—C5	1.404 (8)
S—C9	1.751 (6)	C4—H4A	0.9300
O1—C2	1.360 (5)	C5—C6	1.354 (9)
O1—C1	1.429 (6)	C5—H5A	0.9300
O2—C10	1.226 (5)	C6—C7	1.343 (8)
O3—C12	1.347 (5)	C6—H6A	0.9300
O3—C11	1.436 (5)	C7—H7A	0.9300
O4—H4	0.8501	C10—C13	1.492 (6)
N1—C9	1.329 (6)	C11—H11A	0.9600
N1—N2	1.337 (5)	C11—H11B	0.9600
N2—C8	1.271 (5)	C11—H11C	0.9600
N3—C9	1.171 (6)	C12—C13	1.409 (6)
N3—C10	1.464 (5)	C12—C17	1.411 (7)
N3—H3A	0.8600	C13—C14	1.397 (6)
C1—H1B	0.9600	C14—C15	1.374 (7)
C1—H1C	0.9600	C14—H14A	0.9300
C1—H1D	0.9600	C15—C16	1.364 (8)
C2—C7	1.398 (7)	C15—H15A	0.9300
C2—C3	1.404 (6)	C16—C17	1.361 (7)
C3—C4	1.390 (6)	C16—H16A	0.9300
C3—C8	1.472 (6)	C17—H17A	0.9300

C8—S—C9	87.3 (2)	N2—C8—S	113.1 (3)
C2—O1—C1	118.8 (4)	C3—C8—S	127.2 (3)
C12—O3—C11	118.8 (4)	N3—C9—N1	120.5 (5)
C9—N1—N2	111.7 (4)	N3—C9—S	127.8 (4)
C8—N2—N1	116.1 (4)	N1—C9—S	111.7 (4)
C9—N3—C10	130.6 (4)	O2—C10—N3	115.8 (4)
C9—N3—H3A	114.7	O2—C10—C13	122.2 (4)
C10—N3—H3A	114.7	N3—C10—C13	122.0 (4)
O1—C1—H1B	109.5	O3—C11—H11A	109.5
O1—C1—H1C	109.5	O3—C11—H11B	109.5
H1B—C1—H1C	109.5	H11A—C11—H11B	109.5
O1—C1—H1D	109.5	O3—C11—H11C	109.5
H1B—C1—H1D	109.5	H11A—C11—H11C	109.5
H1C—C1—H1D	109.5	H11B—C11—H11C	109.5
O1—C2—C7	124.0 (5)	O3—C12—C13	117.3 (4)
O1—C2—C3	116.0 (4)	O3—C12—C17	123.6 (4)
C7—C2—C3	120.0 (5)	C13—C12—C17	119.0 (4)
C4—C3—C2	118.5 (4)	C14—C13—C12	118.4 (4)
C4—C3—C8	117.8 (4)	C14—C13—C10	116.0 (4)
C2—C3—C8	123.7 (4)	C12—C13—C10	125.5 (4)
C3—C4—C5	119.4 (6)	C15—C14—C13	121.8 (5)
C3—C4—H4A	120.3	C15—C14—H14A	119.1
C5—C4—H4A	120.3	C13—C14—H14A	119.1
C6—C5—C4	120.7 (6)	C16—C15—C14	118.6 (5)
C6—C5—H5A	119.6	C16—C15—H15A	120.7
C4—C5—H5A	119.6	C14—C15—H15A	120.7
C7—C6—C5	121.0 (6)	C17—C16—C15	122.8 (5)
C7—C6—H6A	119.5	C17—C16—H16A	118.6
C5—C6—H6A	119.5	C15—C16—H16A	118.6
C6—C7—C2	120.4 (5)	C16—C17—C12	119.3 (5)
C6—C7—H7A	119.8	C16—C17—H17A	120.4
C2—C7—H7A	119.8	C12—C17—H17A	120.4
N2—C8—C3	119.6 (4)

C9—N1—N2—C8	1.8 (7)	N2—N1—C9—N3	177.2 (5)
C1—O1—C2—C7	5.2 (7)	N2—N1—C9—S	−1.8 (6)
C1—O1—C2—C3	−174.9 (5)	C8—S—C9—N3	−177.8 (5)
O1—C2—C3—C4	179.6 (4)	C8—S—C9—N1	1.1 (4)
C7—C2—C3—C4	−0.5 (7)	C9—N3—C10—O2	2.0 (7)
O1—C2—C3—C8	−0.8 (7)	C9—N3—C10—C13	−179.0 (5)
C7—C2—C3—C8	179.1 (4)	C11—O3—C12—C13	176.9 (4)
C2—C3—C4—C5	2.2 (8)	C11—O3—C12—C17	−2.3 (7)
C8—C3—C4—C5	−177.4 (5)	O3—C12—C13—C14	−178.2 (4)
C3—C4—C5—C6	−3.0 (10)	C17—C12—C13—C14	1.0 (6)
C4—C5—C6—C7	2.0 (11)	O3—C12—C13—C10	1.1 (6)
C5—C6—C7—C2	−0.3 (10)	C17—C12—C13—C10	−179.7 (4)
O1—C2—C7—C6	179.4 (5)	O2—C10—C13—C14	−2.1 (7)
C3—C2—C7—C6	−0.5 (8)	N3—C10—C13—C14	179.0 (4)
N1—N2—C8—C3	178.5 (4)	O2—C10—C13—C12	178.6 (4)
N1—N2—C8—S	−0.9 (6)	N3—C10—C13—C12	−0.3 (7)
C4—C3—C8—N2	−2.9 (7)	C12—C13—C14—C15	−1.3 (7)
C2—C3—C8—N2	177.5 (5)	C10—C13—C14—C15	179.3 (4)
C4—C3—C8—S	176.4 (4)	C13—C14—C15—C16	−0.7 (8)
C2—C3—C8—S	−3.2 (7)	C14—C15—C16—C17	3.1 (9)
C9—S—C8—N2	−0.2 (4)	C15—C16—C17—C12	−3.5 (8)
C9—S—C8—C3	−179.5 (4)	O3—C12—C17—C16	−179.5 (4)
C10—N3—C9—N1	−179.7 (4)	C13—C12—C17—C16	1.3 (7)
C10—N3—C9—S	−0.9 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O3	0.86	2.04	2.706 (5)	134
O4—H4···N1ⁱ	0.85	2.24	2.796 (6)	123
C14—H14A···O2ⁱⁱ	0.93	2.49	3.316 (6)	148

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅N₃O₃S·0.5H₂O
M_r	350.40
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	29.950 (6), 14.561 (3), 7.6520 (15)
β (°)	94.78 (3)
V (Å³)	3325.4 (12)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.30 × 0.10 × 0.05

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.937, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	6340, 3003, 1602
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.079, 0.241, 1.04
No. of reflections	3003
No. of parameters	222
No. of restraints	?
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.33

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O3	0.86	2.04	2.706 (5)	134.00
O4—H4···N1ⁱ	0.85	2.24	2.796 (6)	123.00
C14—H14A···O2ⁱⁱ	0.93	2.49	3.316 (6)	148.00

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

Acknowledgements

The authors gratefully acknowledge Professor Hua-qin Wang, Analysis Centre, Nanjing University, for providing diffractometer time.

References

Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Nakagawa, Y., Nishimura, K., Izumi, K., Kinoshita, K., Kimura, T. & Kurihara, N. (1996). J. Pestic. Sci. 21, 195–201. CrossRef CAS 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
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, Y. G., Cao, L., Yan, J., Ye, W. F., Zhou, Q. C. & Lu, B. X. (1999). Chem. J. Chin. Univ. 20, 1903–1905. CAS Google Scholar

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Volume 64| Part 8| August 2008| Page o1637

doi:10.1107/S1600536808019934

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-Meth­­oxy-N-[5-(2-meth­oxy­phen­yl)-1,3,4-thia­diazol-2-yl]benzamide hemi­hydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-Methoxy-N-[5-(2-methoxyphenyl)-1,3,4-thiadiazol-2-yl]benzamide hemihydrate