(E)-Ethyl N′-(4-bromo­benzyl­idene)hydrazinecarboxyl­ate

Gao, B.

doi:10.1107/S1600536808023763

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1646

doi:10.1107/S1600536808023763

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(E)-Ethyl N′-(4-bromobenzylidene)hydrazinecarboxylate

Bo Gao ^a ^*

^aMarine College, Zhejiang Institute of Communications, Hangzhou 311112, People's Republic of China
^*Correspondence e-mail: bgao_zjvtit@126.com

(Received 14 July 2008; accepted 27 July 2008; online 31 July 2008)

The title compound, C₁₀H₁₁BrN₂O₂, crystallizes with two independent molecules in the asymmetric unit, in which the dihedral angles between the benzene ring and the hydrazine carboxylic acid mean plane are 3.0 (4) and 45.3 (3)°. The molecules are linked into a one-dimensional network by intermolecular N—H⋯O hydrogen bonds.

Related literature

For general background, see: Parashar et al. (1988 ); Hadjoudis et al.(1987 ); Borg et al. (1999 ). For a related structure, see: Shang et al. (2007 ).

Experimental

Crystal data

C₁₀H₁₁BrN₂O₂
M_r = 271.11
Monoclinic, P 2₁ /c
a = 16.499 (3) Å
b = 8.6052 (19) Å
c = 18.277 (4) Å
β = 116.279 (7)°
V = 2326.7 (8) Å³
Z = 8
Mo Kα radiation
μ = 3.52 mm⁻¹
T = 123 (2) K
0.30 × 0.26 × 0.25 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.419, T_max = 0.474 (expected range = 0.367–0.415)
24092 measured reflections
4075 independent reflections
1989 reflections with I > 2σ(I)
R_int = 0.139

Refinement

R[F² > 2σ(F²)] = 0.093
wR(F²) = 0.259
S = 0.88
4075 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 1.35 e Å⁻³
Δρ_min = −1.10 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3	0.86	2.09	2.913 (7)	161
N4—H4A⋯O1ⁱ	0.86	2.09	2.875 (7)	152
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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: 10.1107/S1600536808023763/hb2762sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808023763/hb2762Isup2.hkl

checkCIF report

Comment top

Benzaldehydehydrazone derivatives have received considerable attention for a long time due to their pharmacological activity (Parashar et al., 1988) and their photochromic properties (Hadjoudis et al., 1987). They are important intermidiates for 1,3,4-oxadiazoles, which have been reported to be versatile compounds with many properties (Borg et al., 1999). As a further investigation of this type of derivatives, the crystal structure of the title compound, (I), is reported here (Fig. 1).

Compound (I) crystallizes with two independent but essentially identical molecules in the asymmetric unit. Each independent molecule adopts a trans configuration with respect to the C═N bond. In each molecule, the hydrazine carboxylic acid methyl ester group is twisted away from the attached ring. The dihedral angle between C1-C6 and N1/N2/O1/O2/C8-C10 planes is 3.0 (4)° and that between C11-C16 and N3/N4/O3/O4/C18 planes is 45.3 (3)°. The bond lengths and angles of each molecule in the asymmetric unit agree with those observed for methyl N'-[(E)-4-methoxybenzylidene]hydrazinecarboxylate (Shang et al., 2007).

In the crystal of (I), the molecules are linked into a one-dimensional network by intermolecular N—H···O hydrogen bonds (Table 1, Fig. 2).

Related literature top

For general background, see: Parashar et al. (1988); Hadjoudis et al.(1987); Borg et al. (1999). For a related structure, see: Shang et al. (2007).

Experimental top

4-Bromobenzaldehyde (1.84 g, 0.01 mol) and ethyl hydrazinecarboxylate (1.04g, 0.01 mol) were dissolved in stirred methanol (20 ml) and left for 3 h at room temperature. The resulting solid was filtered off and recrystallized from ethanol to give the title compound in 85% yield. Colourless blocks of (I) were obtained by slow evaporation of a methanol solution at room temperature (m.p. 433–435 K).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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. Molecular structure of (I), showing 30% probability displacement ellipsoids for the non-hydrogen atoms. The hydrogen bond is shown as a dashed line.
	Fig. 2. The crystal packing of (I). Hydrogen bonds are shown as dashed lines.

(E)-Ethyl N'-(4-bromobenzylidene)hydrazinecarboxylate top

Crystal data top

C₁₀H₁₁BrN₂O₂	F(000) = 1088
M_r = 271.11	D_x = 1.548 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4075 reflections
a = 16.499 (3) Å	θ = 1.4–25.0°
b = 8.6052 (19) Å	µ = 3.52 mm⁻¹
c = 18.277 (4) Å	T = 123 K
β = 116.279 (7)°	Block, colourless
V = 2326.7 (8) Å³	0.30 × 0.26 × 0.25 mm
Z = 8

Data collection top

Bruker SMART CCD diffractometer	4075 independent reflections
Radiation source: fine-focus sealed tube	1989 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.139
ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −19→18
T_min = 0.419, T_max = 0.474	k = −9→10
24092 measured reflections	l = −21→21

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)] = 0.093	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.259	H-atom parameters constrained
S = 0.88	w = 1/[σ²(F_o²) + (0.1543P)²] where P = (F_o² + 2F_c²)/3
4075 reflections	(Δ/σ)_max < 0.001
273 parameters	Δρ_max = 1.35 e Å⁻³
0 restraints	Δρ_min = −1.10 e Å⁻³

Crystal data top

C₁₀H₁₁BrN₂O₂	V = 2326.7 (8) Å³
M_r = 271.11	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.499 (3) Å	µ = 3.52 mm⁻¹
b = 8.6052 (19) Å	T = 123 K
c = 18.277 (4) Å	0.30 × 0.26 × 0.25 mm
β = 116.279 (7)°

Data collection top

Bruker SMART CCD diffractometer	4075 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	1989 reflections with I > 2σ(I)
T_min = 0.419, T_max = 0.474	R_int = 0.139
24092 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.093	0 restraints
wR(F²) = 0.259	H-atom parameters constrained
S = 0.88	Δρ_max = 1.35 e Å⁻³
4075 reflections	Δρ_min = −1.10 e Å⁻³
273 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Br1	−0.38953 (6)	0.41924 (14)	0.35560 (6)	0.1017 (5)
O1	0.1467 (3)	0.9272 (6)	0.6334 (3)	0.0683 (15)
O2	0.2401 (3)	0.9406 (6)	0.5725 (3)	0.0683 (14)
N1	0.0294 (4)	0.7619 (7)	0.4990 (3)	0.0547 (14)
N2	0.1102 (4)	0.8180 (7)	0.5084 (3)	0.0591 (16)
H2A	0.1271	0.8016	0.4708	0.071*
C1	−0.1496 (5)	0.5277 (9)	0.3484 (4)	0.0614 (19)
H1	−0.1226	0.5078	0.3130	0.074*
C2	−0.2340 (6)	0.4681 (9)	0.3288 (4)	0.068 (2)
H2	−0.2657	0.4103	0.2801	0.082*
C3	−0.2716 (5)	0.4947 (10)	0.3822 (5)	0.069 (2)
C4	−0.2254 (6)	0.5766 (10)	0.4538 (5)	0.079 (2)
H4	−0.2513	0.5928	0.4905	0.094*
C5	−0.1413 (5)	0.6341 (10)	0.4709 (4)	0.069 (2)
H5	−0.1087	0.6882	0.5208	0.082*
C6	−0.1020 (5)	0.6165 (8)	0.4185 (4)	0.0540 (17)
C7	−0.0147 (5)	0.6797 (9)	0.4356 (4)	0.0566 (18)
H7	0.0106	0.6598	0.3988	0.068*
C8	0.1647 (5)	0.8967 (9)	0.5765 (4)	0.0593 (19)
C9	0.3059 (5)	1.0219 (11)	0.6442 (4)	0.075 (2)
H9A	0.3253	0.9547	0.6930	0.090*
H9B	0.2789	1.1178	0.6539	0.090*
C10	0.3843 (6)	1.0610 (15)	0.6288 (6)	0.113 (4)
H10A	0.4283	1.1208	0.6749	0.170*
H10B	0.3639	1.1230	0.5788	0.170*
H10C	0.4126	0.9650	0.6225	0.170*
Br2	−0.40506 (7)	0.72172 (16)	0.13867 (7)	0.1115 (5)
O3	0.2037 (4)	0.7286 (7)	0.4120 (3)	0.0764 (16)
O4	0.2853 (3)	0.6993 (6)	0.3405 (3)	0.0672 (14)
N3	0.0511 (4)	0.7304 (7)	0.2633 (3)	0.0555 (15)
N4	0.1369 (4)	0.7146 (7)	0.2717 (3)	0.0589 (15)
H4A	0.1461	0.7048	0.2291	0.071*
C11	−0.2224 (5)	0.8208 (9)	0.2063 (5)	0.065 (2)
H11	−0.2410	0.8950	0.2342	0.078*
C12	−0.2835 (6)	0.7232 (10)	0.1526 (5)	0.072 (2)
C13	−0.2584 (6)	0.6157 (10)	0.1077 (4)	0.074 (2)
H13	−0.3017	0.5477	0.0693	0.089*
C14	−0.1333 (5)	0.8142 (9)	0.2212 (4)	0.063 (2)
H14	−0.0904	0.8821	0.2601	0.075*
C15	−0.1705 (5)	0.6125 (9)	0.1210 (4)	0.064 (2)
H15	−0.1532	0.5435	0.0898	0.076*
C16	−0.1055 (5)	0.7070 (8)	0.1786 (4)	0.0530 (17)
C17	−0.0116 (5)	0.6937 (8)	0.1946 (4)	0.0549 (18)
H17	0.0029	0.6569	0.1529	0.066*
C18	0.2083 (5)	0.7143 (9)	0.3472 (4)	0.0604 (19)
C19	0.3667 (6)	0.6862 (12)	0.4155 (5)	0.087 (3)
H19A	0.3691	0.5839	0.4411	0.105*
H19B	0.3689	0.7686	0.4541	0.105*
C20	0.4441 (7)	0.7027 (18)	0.3950 (8)	0.134 (5)
H20A	0.5009	0.6958	0.4451	0.201*
H20B	0.4406	0.8038	0.3691	0.201*
H20C	0.4418	0.6196	0.3575	0.201*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0722 (7)	0.1265 (10)	0.1016 (8)	−0.0210 (5)	0.0342 (6)	−0.0047 (6)
O1	0.076 (4)	0.094 (4)	0.044 (3)	−0.011 (3)	0.035 (3)	−0.005 (2)
O2	0.054 (3)	0.110 (4)	0.048 (3)	−0.014 (3)	0.029 (2)	−0.005 (3)
N1	0.053 (4)	0.068 (4)	0.049 (3)	0.001 (3)	0.028 (3)	0.004 (3)
N2	0.053 (4)	0.091 (5)	0.037 (3)	−0.003 (3)	0.024 (3)	−0.005 (3)
C1	0.078 (6)	0.063 (5)	0.051 (4)	−0.001 (4)	0.036 (4)	−0.001 (4)
C2	0.081 (6)	0.073 (5)	0.050 (4)	0.008 (5)	0.028 (4)	−0.003 (4)
C3	0.065 (5)	0.069 (5)	0.065 (5)	0.003 (4)	0.022 (4)	0.005 (4)
C4	0.076 (6)	0.104 (7)	0.068 (5)	0.001 (5)	0.043 (4)	−0.009 (5)
C5	0.072 (5)	0.088 (6)	0.052 (4)	−0.012 (5)	0.033 (4)	−0.011 (4)
C6	0.062 (5)	0.058 (4)	0.044 (4)	0.007 (4)	0.026 (3)	0.004 (3)
C7	0.057 (4)	0.073 (5)	0.044 (4)	0.006 (4)	0.027 (4)	−0.003 (4)
C8	0.052 (4)	0.076 (5)	0.048 (4)	0.005 (4)	0.020 (4)	0.015 (4)
C9	0.063 (5)	0.102 (6)	0.056 (5)	−0.016 (5)	0.023 (4)	0.001 (4)
C10	0.073 (7)	0.173 (12)	0.080 (6)	−0.040 (7)	0.021 (5)	−0.003 (7)
Br2	0.0600 (7)	0.1507 (11)	0.1204 (9)	−0.0002 (6)	0.0369 (6)	0.0102 (7)
O3	0.082 (4)	0.108 (4)	0.050 (3)	0.009 (3)	0.038 (3)	−0.003 (3)
O4	0.054 (3)	0.101 (4)	0.052 (3)	0.004 (3)	0.028 (2)	0.001 (3)
N3	0.058 (4)	0.067 (4)	0.055 (4)	0.005 (3)	0.037 (3)	0.007 (3)
N4	0.062 (4)	0.077 (4)	0.046 (3)	0.001 (3)	0.032 (3)	0.003 (3)
C11	0.063 (5)	0.069 (5)	0.072 (5)	0.002 (4)	0.037 (4)	−0.012 (4)
C12	0.065 (5)	0.085 (6)	0.056 (4)	−0.001 (4)	0.020 (4)	0.014 (4)
C13	0.083 (6)	0.077 (6)	0.050 (4)	−0.015 (5)	0.019 (4)	−0.008 (4)
C14	0.073 (5)	0.066 (5)	0.054 (4)	0.000 (4)	0.032 (4)	−0.007 (4)
C15	0.066 (5)	0.076 (5)	0.049 (4)	0.004 (4)	0.026 (4)	−0.008 (4)
C16	0.069 (5)	0.053 (4)	0.041 (3)	0.003 (4)	0.027 (3)	0.005 (3)
C17	0.065 (5)	0.064 (5)	0.041 (4)	0.009 (4)	0.029 (4)	−0.001 (3)
C18	0.067 (5)	0.064 (5)	0.057 (5)	−0.001 (4)	0.033 (4)	0.002 (4)
C19	0.079 (6)	0.116 (8)	0.063 (5)	0.008 (5)	0.027 (5)	−0.001 (5)
C20	0.065 (7)	0.215 (15)	0.112 (8)	−0.001 (7)	0.030 (6)	−0.005 (9)

Geometric parameters (Å, º) top

Br1—C3	1.899 (8)	Br2—C12	1.907 (8)
O1—C8	1.229 (8)	O3—C18	1.226 (8)
O2—C8	1.333 (9)	O4—C18	1.335 (9)
O2—C9	1.458 (9)	O4—C19	1.437 (10)
N1—C7	1.275 (8)	N3—C17	1.264 (8)
N1—N2	1.355 (8)	N3—N4	1.360 (8)
N2—C8	1.352 (9)	N4—C18	1.361 (9)
N2—H2A	0.8600	N4—H4A	0.8601
C1—C2	1.374 (10)	C11—C12	1.344 (11)
C1—C6	1.396 (10)	C11—C14	1.372 (10)
C1—H1	0.9500	C11—H11	0.9500
C2—C3	1.387 (10)	C12—C13	1.415 (12)
C2—H2	0.9500	C13—C15	1.360 (11)
C3—C4	1.381 (11)	C13—H13	0.9500
C4—C5	1.373 (11)	C14—C16	1.407 (10)
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.382 (10)	C15—C16	1.386 (10)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.439 (10)	C16—C17	1.447 (10)
C7—H7	0.9500	C17—H17	0.9500
C9—C10	1.478 (11)	C19—C20	1.487 (14)
C9—H9A	0.9900	C19—H19A	0.9900
C9—H9B	0.9900	C19—H19B	0.9900
C10—H10A	0.9800	C20—H20A	0.9800
C10—H10B	0.9800	C20—H20B	0.9800
C10—H10C	0.9800	C20—H20C	0.9800

C8—O2—C9	115.4 (5)	C18—O4—C19	116.6 (5)
C7—N1—N2	116.5 (5)	C17—N3—N4	116.1 (5)
C8—N2—N1	120.8 (5)	N3—N4—C18	120.3 (5)
C8—N2—H2A	119.9	N3—N4—H4A	120.0
N1—N2—H2A	119.2	C18—N4—H4A	119.7
C2—C1—C6	122.4 (7)	C12—C11—C14	120.7 (7)
C2—C1—H1	118.8	C12—C11—H11	119.6
C6—C1—H1	118.8	C14—C11—H11	119.6
C1—C2—C3	118.2 (7)	C11—C12—C13	120.9 (8)
C1—C2—H2	120.9	C11—C12—Br2	120.4 (7)
C3—C2—H2	120.9	C13—C12—Br2	118.6 (7)
C4—C3—C2	121.3 (8)	C15—C13—C12	118.2 (7)
C4—C3—Br1	119.4 (6)	C15—C13—H13	120.9
C2—C3—Br1	119.4 (6)	C12—C13—H13	120.9
C5—C4—C3	118.6 (7)	C11—C14—C16	120.0 (7)
C5—C4—H4	120.7	C11—C14—H14	120.0
C3—C4—H4	120.7	C16—C14—H14	120.0
C4—C5—C6	122.6 (7)	C13—C15—C16	121.9 (7)
C4—C5—H5	118.7	C13—C15—H15	119.1
C6—C5—H5	118.7	C16—C15—H15	119.1
C5—C6—C1	116.8 (7)	C15—C16—C14	118.2 (7)
C5—C6—C7	122.7 (7)	C15—C16—C17	120.3 (6)
C1—C6—C7	120.5 (6)	C14—C16—C17	121.4 (7)
N1—C7—C6	121.3 (6)	N3—C17—C16	120.9 (6)
N1—C7—H7	119.3	N3—C17—H17	119.6
C6—C7—H7	119.3	C16—C17—H17	119.6
O1—C8—O2	124.6 (7)	O3—C18—O4	124.5 (7)
O1—C8—N2	125.0 (7)	O3—C18—N4	125.6 (7)
O2—C8—N2	110.4 (6)	O4—C18—N4	109.9 (6)
O2—C9—C10	107.7 (7)	O4—C19—C20	107.3 (7)
O2—C9—H9A	110.2	O4—C19—H19A	110.2
C10—C9—H9A	110.2	C20—C19—H19A	110.2
O2—C9—H9B	110.2	O4—C19—H19B	110.2
C10—C9—H9B	110.2	C20—C19—H19B	110.2
H9A—C9—H9B	108.5	H19A—C19—H19B	108.5
C9—C10—H10A	109.5	C19—C20—H20A	109.5
C9—C10—H10B	109.5	C19—C20—H20B	109.5
H10A—C10—H10B	109.5	H20A—C20—H20B	109.5
C9—C10—H10C	109.5	C19—C20—H20C	109.5
H10A—C10—H10C	109.5	H20A—C20—H20C	109.5
H10B—C10—H10C	109.5	H20B—C20—H20C	109.5

C7—N1—N2—C8	−175.2 (7)	C17—N3—N4—C18	−164.0 (7)
C6—C1—C2—C3	−1.6 (11)	C14—C11—C12—C13	−2.6 (12)
C1—C2—C3—C4	−1.0 (12)	C14—C11—C12—Br2	175.0 (6)
C1—C2—C3—Br1	178.2 (6)	C11—C12—C13—C15	0.7 (12)
C2—C3—C4—C5	1.0 (12)	Br2—C12—C13—C15	−176.9 (6)
Br1—C3—C4—C5	−178.2 (6)	C12—C11—C14—C16	1.5 (11)
C3—C4—C5—C6	1.6 (13)	C12—C13—C15—C16	2.2 (11)
C4—C5—C6—C1	−4.0 (12)	C13—C15—C16—C14	−3.3 (11)
C4—C5—C6—C7	178.6 (7)	C13—C15—C16—C17	176.2 (7)
C2—C1—C6—C5	4.0 (11)	C11—C14—C16—C15	1.4 (10)
C2—C1—C6—C7	−178.5 (7)	C11—C14—C16—C17	−178.1 (7)
N2—N1—C7—C6	−178.9 (6)	N4—N3—C17—C16	−179.5 (6)
C5—C6—C7—N1	−3.2 (11)	C15—C16—C17—N3	−153.1 (7)
C1—C6—C7—N1	179.5 (7)	C14—C16—C17—N3	26.4 (10)
C9—O2—C8—O1	3.9 (10)	C19—O4—C18—O3	5.5 (11)
C9—O2—C8—N2	−177.8 (6)	C19—O4—C18—N4	−175.8 (7)
N1—N2—C8—O1	−1.6 (11)	N3—N4—C18—O3	−0.6 (11)
N1—N2—C8—O2	−179.9 (6)	N3—N4—C18—O4	−179.3 (6)
C8—O2—C9—C10	180.0 (8)	C18—O4—C19—C20	−168.8 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3	0.86	2.09	2.913 (7)	161
N4—H4A···O1ⁱ	0.86	2.09	2.875 (7)	152

Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₁BrN₂O₂
M_r	271.11
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	123
a, b, c (Å)	16.499 (3), 8.6052 (19), 18.277 (4)
β (°)	116.279 (7)
V (Å³)	2326.7 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.52
Crystal size (mm)	0.30 × 0.26 × 0.25

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.419, 0.474
No. of measured, independent and observed [I > 2σ(I)] reflections	24092, 4075, 1989
R_int	0.139
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.093, 0.259, 0.88
No. of reflections	4075
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.35, −1.10

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), 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
N2—H2A···O3	0.86	2.09	2.913 (7)	161
N4—H4A···O1ⁱ	0.86	2.09	2.875 (7)	152

Symmetry code: (i) x, −y+3/2, z−1/2.

Acknowledgements

The author acknowledges the financial support of Zhejiang Institute of Communications, China.

References

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