(E)-Methyl N′-(4-bromo­benzyl­idene)­hydrazinecarboxyl­ate at 123 K

Sun, R.; Cheng, X.-W.

doi:10.1107/S1600536808021983

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1544

doi:10.1107/S1600536808021983

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(E)-Methyl N′-(4-bromobenzylidene)hydrazinecarboxylate at 123 K

Rong Sun ^a and Xiang-Wei Cheng ^a ^*

^aZhejiang Police College Experience Center, Zhejiang Police College, Hangzhou 310053, People's Republic of China
^*Correspondence e-mail: zpccxw@126.com

(Received 12 July 2008; accepted 14 July 2008; online 19 July 2008)

The title compound, C₉H₉BrN₂O₂, crystallizes with two independent but essentially identical molecules in the asymmetric unit. Each molecule adopts a trans configuration with respect to the C=N bond. In one of the molecules, the dihedral angle between the benzene ring and the hydrazinecarboxylic acid plane is 24.9 (2)°, and that in the other molecule is 16.1 (2)°. The molecules are linked into a three-dimensional network via intermolecular N—H⋯O, C—H⋯O, C—H⋯N and C—H⋯Br hydrogen bonds. An intramolecular N—H⋯O hydrogen bond is also present.

Related literature

For general background, see: Parashar et al. (1988 ); Hadjoudis et al. (1987 ); Borg et al. (1999 ). For a related structure, see: Cheng (2008 ).

Experimental

Crystal data

C₉H₉BrN₂O₂
M_r = 257.09
Monoclinic, P 2₁ /c
a = 13.8585 (10) Å
b = 9.5257 (7) Å
c = 15.5871 (11) Å
β = 95.967 (3)°
V = 2046.5 (3) Å³
Z = 8
Mo Kα radiation
μ = 3.99 mm⁻¹
T = 123 (2) K
0.30 × 0.26 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.320, T_max = 0.367
20978 measured reflections
3610 independent reflections
2615 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.099
S = 1.05
3610 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.76 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3ⁱ	0.88	2.01	2.854 (4)	160
N4—H4A⋯O1	0.88	2.04	2.896 (3)	165
C7—H7⋯O3ⁱ	0.95	2.49	3.261 (4)	139
C9—H9A⋯Br2ⁱⁱ	0.98	2.89	3.697 (3)	141
C18—H18C⋯N1ⁱⁱⁱ	0.98	2.60	3.548 (5)	162
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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/S1600536808021983/ci2632sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808021983/ci2632Isup2.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 is reported here.

The title molecule (Fig.1) 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/C7-C9 planes is 24.9 (2)° and that between C10-C15 and N3/N4/O3/O4/C16-C18 planes is 14.8 (2)°. The bond lengths and angles of each molecule in the asymmetric unit agree with those observed for ethyl N'-[(E)-4-hydroxybenzylidene]hydrazinecarboxylate (Cheng, 2008). The independent molecules are linked through N4-H4A···O1 hydrogen bond.

The molecules are linked into a three-dimensional network by intermolecular N—H···O, C—H···O, C—H···N and C—H···Br hydrogen bonds (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: Cheng (2008).

Experimental top

4-Bromobenzaldehyde (1.84 g, 0.01 mol) and methyl hydrazinecarboxylate (0.90 g, 0.01 mol) were dissolved in stirred methanol (25 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 75% yield. Single crystals suitable for X-ray analysis were obtained by slow evaporation of a methanol solution at room temperature (m.p. 459–462 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 the title compound, showing 30% probability displacement ellipsoids and the atomic numbering.
	Fig. 2. The crystal packing of the title compound. Hydrogen bonds are shown as dashed lines.

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

Crystal data top

C₉H₉BrN₂O₂	F(000) = 1024
M_r = 257.09	D_x = 1.669 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3610 reflections
a = 13.8585 (10) Å	θ = 1.5–25.0°
b = 9.5257 (7) Å	µ = 3.99 mm⁻¹
c = 15.5871 (11) Å	T = 123 K
β = 95.967 (3)°	Block, colourless
V = 2046.5 (3) Å³	0.30 × 0.26 × 0.25 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	3610 independent reflections
Radiation source: fine-focus sealed tube	2615 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −16→16
T_min = 0.320, T_max = 0.368	k = −11→9
20978 measured reflections	l = −18→18

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)] = 0.036	H-atom parameters constrained
wR(F²) = 0.099	w = 1/[σ²(F_o²) + (0.048P)² + 0.8965P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
3610 reflections	Δρ_max = 0.76 e Å⁻³
254 parameters	Δρ_min = −0.49 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0078 (6)

Crystal data top

C₉H₉BrN₂O₂	V = 2046.5 (3) Å³
M_r = 257.09	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.8585 (10) Å	µ = 3.99 mm⁻¹
b = 9.5257 (7) Å	T = 123 K
c = 15.5871 (11) Å	0.30 × 0.26 × 0.25 mm
β = 95.967 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3610 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	2615 reflections with I > 2σ(I)
T_min = 0.320, T_max = 0.368	R_int = 0.056
20978 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.05	Δρ_max = 0.76 e Å⁻³
3610 reflections	Δρ_min = −0.49 e Å⁻³
254 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
Br2	0.54645 (3)	0.79291 (5)	0.97542 (3)	0.07171 (19)
Br1	0.53903 (3)	0.13944 (5)	0.80455 (3)	0.0767 (2)
O2	−0.13460 (16)	0.5200 (3)	0.56109 (14)	0.0519 (6)
O1	−0.05639 (17)	0.5733 (3)	0.69189 (14)	0.0545 (6)
O3	−0.01087 (16)	0.2800 (3)	0.95955 (15)	0.0562 (6)
O4	−0.12520 (16)	0.3158 (3)	0.84755 (15)	0.0558 (6)
N2	−0.00584 (19)	0.3978 (3)	0.60735 (17)	0.0473 (7)
H2A	−0.0224	0.3431	0.5628	0.057*
N4	0.0057 (2)	0.4480 (3)	0.85778 (17)	0.0484 (7)
H4A	−0.0223	0.4915	0.8120	0.058*
N3	0.09646 (19)	0.4870 (3)	0.89337 (16)	0.0473 (7)
N1	0.07984 (19)	0.3755 (3)	0.65906 (16)	0.0447 (7)
C8	−0.0638 (2)	0.5048 (4)	0.6263 (2)	0.0423 (7)
C6	0.2240 (2)	0.2373 (3)	0.6832 (2)	0.0420 (7)
C7	0.1282 (2)	0.2684 (4)	0.6391 (2)	0.0443 (8)
H7	0.1012	0.2075	0.5946	0.053*
C16	0.1337 (2)	0.5923 (4)	0.8575 (2)	0.0473 (8)
H16	0.0977	0.6392	0.8109	0.057*
C14	0.2665 (3)	0.7650 (4)	0.8564 (2)	0.0527 (9)
H14	0.2265	0.8183	0.8154	0.063*
C3	0.2686 (3)	0.1104 (4)	0.6674 (2)	0.0519 (9)
H3	0.2350	0.0434	0.6304	0.062*
C17	−0.0398 (2)	0.3416 (4)	0.8945 (2)	0.0435 (8)
C15	0.2313 (2)	0.6402 (3)	0.8879 (2)	0.0449 (8)
C18	−0.1841 (3)	0.2064 (4)	0.8805 (3)	0.0655 (10)
H18A	−0.2442	0.1955	0.8421	0.098*
H18B	−0.1998	0.2321	0.9384	0.098*
H18C	−0.1481	0.1177	0.8835	0.098*
C4	0.3665 (2)	0.3015 (4)	0.7766 (2)	0.0519 (9)
H4	0.4004	0.3664	0.8150	0.062*
C2	0.3607 (3)	0.0802 (4)	0.7048 (2)	0.0566 (9)
H2	0.3904	−0.0069	0.6937	0.068*
C5	0.2746 (3)	0.3315 (4)	0.7396 (2)	0.0508 (9)
H5	0.2450	0.4178	0.7526	0.061*
C13	0.2918 (3)	0.5639 (4)	0.9480 (2)	0.0552 (9)
H13	0.2691	0.4785	0.9703	0.066*
C10	0.3585 (3)	0.8122 (4)	0.8839 (2)	0.0562 (9)
H10	0.3815	0.8979	0.8625	0.067*
C11	0.4167 (2)	0.7338 (4)	0.9426 (2)	0.0521 (9)
C1	0.4090 (2)	0.1767 (4)	0.7578 (2)	0.0484 (8)
C9	−0.2049 (3)	0.6282 (4)	0.5732 (3)	0.0651 (10)
H9A	−0.2534	0.6314	0.5228	0.098*
H9B	−0.1721	0.7192	0.5802	0.098*
H9C	−0.2371	0.6073	0.6248	0.098*
C12	0.3837 (3)	0.6103 (4)	0.9756 (2)	0.0575 (9)
H12	0.4241	0.5578	1.0168	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br2	0.0498 (2)	0.0817 (3)	0.0820 (3)	−0.0070 (2)	−0.00095 (19)	−0.0060 (2)
Br1	0.0418 (2)	0.1006 (4)	0.0865 (3)	0.0154 (2)	0.00182 (18)	0.0141 (2)
O2	0.0420 (12)	0.0612 (15)	0.0504 (13)	0.0084 (11)	−0.0059 (10)	−0.0043 (11)
O1	0.0605 (15)	0.0590 (15)	0.0427 (13)	0.0140 (12)	−0.0011 (11)	−0.0030 (12)
O3	0.0524 (14)	0.0644 (17)	0.0493 (14)	0.0002 (12)	−0.0066 (11)	0.0131 (12)
O4	0.0439 (13)	0.0578 (15)	0.0625 (14)	−0.0003 (11)	−0.0102 (11)	0.0068 (12)
N2	0.0409 (15)	0.0501 (17)	0.0487 (15)	0.0057 (13)	−0.0060 (12)	−0.0100 (13)
N4	0.0487 (16)	0.0476 (18)	0.0459 (15)	0.0009 (13)	−0.0096 (12)	0.0090 (13)
N3	0.0452 (16)	0.0499 (18)	0.0453 (15)	0.0034 (13)	−0.0025 (12)	−0.0006 (13)
N1	0.0415 (15)	0.0497 (18)	0.0420 (14)	0.0004 (13)	−0.0005 (11)	0.0008 (12)
C8	0.0357 (16)	0.049 (2)	0.0417 (18)	−0.0013 (15)	0.0014 (13)	0.0047 (16)
C6	0.0416 (17)	0.0395 (19)	0.0449 (17)	0.0017 (15)	0.0045 (13)	0.0022 (14)
C7	0.0448 (18)	0.040 (2)	0.0470 (18)	−0.0026 (15)	0.0012 (14)	−0.0019 (15)
C16	0.052 (2)	0.045 (2)	0.0430 (18)	0.0084 (16)	0.0009 (15)	−0.0022 (16)
C14	0.057 (2)	0.048 (2)	0.052 (2)	0.0085 (17)	−0.0007 (16)	0.0052 (17)
C3	0.055 (2)	0.043 (2)	0.057 (2)	−0.0030 (17)	0.0008 (16)	−0.0047 (16)
C17	0.0405 (17)	0.045 (2)	0.0437 (18)	0.0097 (15)	−0.0005 (14)	−0.0026 (15)
C15	0.0474 (18)	0.043 (2)	0.0436 (17)	0.0068 (16)	0.0022 (14)	−0.0030 (15)
C18	0.048 (2)	0.070 (3)	0.078 (3)	−0.005 (2)	−0.0002 (18)	0.001 (2)
C4	0.0491 (19)	0.048 (2)	0.056 (2)	−0.0009 (17)	−0.0036 (16)	−0.0030 (16)
C2	0.055 (2)	0.049 (2)	0.068 (2)	0.0130 (18)	0.0124 (18)	0.0032 (18)
C5	0.053 (2)	0.043 (2)	0.055 (2)	0.0035 (16)	−0.0003 (16)	−0.0064 (16)
C13	0.061 (2)	0.045 (2)	0.058 (2)	0.0010 (18)	0.0006 (17)	0.0061 (17)
C10	0.059 (2)	0.052 (2)	0.058 (2)	−0.0010 (18)	0.0059 (17)	0.0058 (17)
C11	0.0416 (18)	0.057 (2)	0.057 (2)	0.0005 (17)	0.0024 (15)	−0.0102 (17)
C1	0.0379 (17)	0.054 (2)	0.0537 (19)	0.0032 (16)	0.0041 (15)	0.0096 (17)
C9	0.0423 (19)	0.072 (3)	0.078 (3)	0.0148 (19)	−0.0051 (18)	0.004 (2)
C12	0.054 (2)	0.053 (2)	0.062 (2)	0.0061 (18)	−0.0060 (17)	0.0071 (18)

Geometric parameters (Å, º) top

Br2—C11	1.903 (3)	C14—C15	1.394 (5)
Br1—C1	1.906 (3)	C14—H14	0.95
O2—C8	1.345 (4)	C3—C2	1.377 (5)
O2—C9	1.445 (4)	C3—H3	0.95
O1—C8	1.208 (4)	C15—C13	1.394 (5)
O3—C17	1.204 (4)	C18—H18A	0.98
O4—C17	1.348 (4)	C18—H18B	0.98
O4—C18	1.450 (5)	C18—H18C	0.98
N2—C8	1.349 (4)	C4—C1	1.371 (5)
N2—N1	1.380 (3)	C4—C5	1.374 (5)
N2—H2A	0.88	C4—H4	0.95
N4—C17	1.352 (4)	C2—C1	1.364 (5)
N4—N3	1.372 (4)	C2—H2	0.95
N4—H4A	0.88	C5—H5	0.95
N3—C16	1.283 (4)	C13—C12	1.375 (5)
N1—C7	1.277 (4)	C13—H13	0.95
C6—C5	1.393 (4)	C10—C11	1.376 (5)
C6—C3	1.392 (5)	C10—H10	0.95
C6—C7	1.460 (4)	C11—C12	1.380 (5)
C7—H7	0.95	C9—H9A	0.98
C16—C15	1.458 (5)	C9—H9B	0.98
C16—H16	0.95	C9—H9C	0.98
C14—C10	1.377 (5)	C12—H12	0.95

C8—O2—C9	115.3 (3)	O4—C18—H18B	109.5
C17—O4—C18	115.7 (3)	H18A—C18—H18B	109.5
C8—N2—N1	118.9 (3)	O4—C18—H18C	109.5
C8—N2—H2A	120.5	H18A—C18—H18C	109.5
N1—N2—H2A	120.5	H18B—C18—H18C	109.5
C17—N4—N3	118.7 (3)	C1—C4—C5	119.4 (3)
C17—N4—H4A	120.7	C1—C4—H4	120.3
N3—N4—H4A	120.7	C5—C4—H4	120.3
C16—N3—N4	115.4 (3)	C1—C2—C3	119.4 (3)
C7—N1—N2	115.0 (3)	C1—C2—H2	120.3
O1—C8—O2	124.9 (3)	C3—C2—H2	120.3
O1—C8—N2	126.4 (3)	C4—C5—C6	121.0 (3)
O2—C8—N2	108.6 (3)	C4—C5—H5	119.5
C5—C6—C3	117.9 (3)	C6—C5—H5	119.5
C5—C6—C7	122.7 (3)	C12—C13—C15	121.0 (3)
C3—C6—C7	119.5 (3)	C12—C13—H13	119.5
N1—C7—C6	121.4 (3)	C15—C13—H13	119.5
N1—C7—H7	119.3	C14—C10—C11	119.3 (3)
C6—C7—H7	119.3	C14—C10—H10	120.4
N3—C16—C15	120.3 (3)	C11—C10—H10	120.4
N3—C16—H16	119.9	C10—C11—C12	121.1 (3)
C15—C16—H16	119.9	C10—C11—Br2	119.3 (3)
C10—C14—C15	121.1 (3)	C12—C11—Br2	119.5 (3)
C10—C14—H14	119.5	C2—C1—C4	121.3 (3)
C15—C14—H14	119.5	C2—C1—Br1	119.4 (3)
C2—C3—C6	121.1 (3)	C4—C1—Br1	119.3 (3)
C2—C3—H3	119.5	O2—C9—H9A	109.5
C6—C3—H3	119.5	O2—C9—H9B	109.5
O3—C17—O4	124.4 (3)	H9A—C9—H9B	109.5
O3—C17—N4	126.4 (3)	O2—C9—H9C	109.5
O4—C17—N4	109.2 (3)	H9A—C9—H9C	109.5
C13—C15—C14	118.2 (3)	H9B—C9—H9C	109.5
C13—C15—C16	121.8 (3)	C13—C12—C11	119.3 (3)
C14—C15—C16	120.0 (3)	C13—C12—H12	120.3
O4—C18—H18A	109.5	C11—C12—H12	120.3

C17—N4—N3—C16	−177.3 (3)	N3—C16—C15—C13	8.7 (5)
C8—N2—N1—C7	176.9 (3)	N3—C16—C15—C14	−171.7 (3)
C9—O2—C8—O1	0.5 (5)	C6—C3—C2—C1	−0.2 (5)
C9—O2—C8—N2	178.0 (3)	C1—C4—C5—C6	0.0 (5)
N1—N2—C8—O1	−11.7 (5)	C3—C6—C5—C4	1.7 (5)
N1—N2—C8—O2	170.8 (3)	C7—C6—C5—C4	−176.8 (3)
N2—N1—C7—C6	174.9 (3)	C14—C15—C13—C12	0.0 (5)
C5—C6—C7—N1	−9.9 (5)	C16—C15—C13—C12	179.6 (3)
C3—C6—C7—N1	171.6 (3)	C15—C14—C10—C11	0.7 (5)
N4—N3—C16—C15	−177.9 (3)	C14—C10—C11—C12	−1.2 (6)
C5—C6—C3—C2	−1.6 (5)	C14—C10—C11—Br2	176.3 (3)
C7—C6—C3—C2	177.0 (3)	C3—C2—C1—C4	2.0 (5)
C18—O4—C17—O3	0.5 (5)	C3—C2—C1—Br1	−176.7 (3)
C18—O4—C17—N4	−178.2 (3)	C5—C4—C1—C2	−1.8 (5)
N3—N4—C17—O3	4.3 (5)	C5—C4—C1—Br1	176.8 (3)
N3—N4—C17—O4	−177.0 (3)	C15—C13—C12—C11	−0.5 (6)
C10—C14—C15—C13	−0.1 (5)	C10—C11—C12—C13	1.1 (6)
C10—C14—C15—C16	−179.7 (3)	Br2—C11—C12—C13	−176.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3ⁱ	0.88	2.01	2.854 (4)	160
N4—H4A···O1	0.88	2.04	2.896 (3)	165
C7—H7···O3ⁱ	0.95	2.49	3.261 (4)	139
C9—H9A···Br2ⁱⁱ	0.98	2.89	3.697 (3)	141
C18—H18C···N1ⁱⁱⁱ	0.98	2.60	3.548 (5)	162

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

Experimental details

Crystal data
Chemical formula	C₉H₉BrN₂O₂
M_r	257.09
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	123
a, b, c (Å)	13.8585 (10), 9.5257 (7), 15.5871 (11)
β (°)	95.967 (3)
V (Å³)	2046.5 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.99
Crystal size (mm)	0.30 × 0.26 × 0.25

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.320, 0.368
No. of measured, independent and observed [I > 2σ(I)] reflections	20978, 3610, 2615
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.099, 1.05
No. of reflections	3610
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.76, −0.49

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···O3ⁱ	0.88	2.01	2.854 (4)	160
N4—H4A···O1	0.88	2.04	2.896 (3)	165
C7—H7···O3ⁱ	0.95	2.49	3.261 (4)	139
C9—H9A···Br2ⁱⁱ	0.98	2.89	3.697 (3)	141
C18—H18C···N1ⁱⁱⁱ	0.98	2.60	3.548 (5)	162

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

Acknowledgements

The authors acknowledge financial support from Zhejiang Police College, China.

References

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