(E)-N′-(5-Bromo-2-meth­oxy­benzyl­idene)isonicotinohydrazide

Ban, H.-Y.

doi:10.1107/S1600536811017910

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1443

doi:10.1107/S1600536811017910

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(E)-N′-(5-Bromo-2-methoxybenzylidene)isonicotinohydrazide

Hong-Yan Ban ^a ^*

^aSchool of Chemical Engineering, University of Science and Technology Liaoning, Anshan 114051, People's Republic of China
^*Correspondence e-mail: hongyan_ban@163.com

(Received 11 May 2011; accepted 12 May 2011; online 20 May 2011)

The asymmetric unit of the title compound, C₁₄H₁₂BrN₃O₂, contains two independent molecules in which the dihedral angles between the benzene ring and the pyridine ring are 24.4 (6) and 23.7 (6)°. The molecules exist in a trans configuration with respect to the central methylidene units. In the crystal, molecules are linked through intermolecular N—H⋯O hydrogen bonds, forming chains along the a axis.

Related literature

For the biological activity of hydrazones, see: Zhong et al. (2007 ); Raj et al. (2007 ); Jimenez-Pulido et al. (2008 ). For related structures, see: Ban (2010 ); Ban & Li (2008a ,b ); Li & Ban (2009a ,b ); Yehye et al. (2008 ); Fun et al. (2008a ,b ); Yang et al. (2008 ); Ejsmont et al. (2008 ); Yang (2006 ).

Experimental

Crystal data

C₁₄H₁₂BrN₃O₂
M_r = 334.18
Monoclinic, P 2₁ /c
a = 10.020 (3) Å
b = 25.732 (2) Å
c = 11.243 (2) Å
β = 102.199 (3)°
V = 2833.4 (10) Å³
Z = 8
Mo Kα radiation
μ = 2.91 mm⁻¹
T = 298 K
0.13 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.704, T_max = 0.760
14099 measured reflections
5922 independent reflections
2018 reflections with I > 2σ(I)
R_int = 0.114

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.143
S = 0.94
5922 reflections
369 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5⋯O2	0.90 (1)	2.06 (2)	2.939 (7)	164 (6)
N2—H2⋯O4ⁱ	0.90 (1)	2.11 (2)	2.999 (7)	168 (6)
Symmetry code: (i) x+1, y, z.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); 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 global, I. DOI: 10.1107/S1600536811017910/sj5145sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811017910/sj5145Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811017910/sj5145Isup3.cml

checkCIF report

Comment top

Hydrazone compounds derived from the condensation of aldehydes with hydrazides have been demonstrated to possess excellent biological activities (Zhong et al., 2007; Raj et al., 2007; Jimenez-Pulido et al., 2008). Due to the easy synthesis of such compounds, a number of hydrazone compounds have been synthesized and structurally characterized (Yehye et al., 2008; Fun et al., 2008a,b; Yang et al., 2008; Ejsmont et al., 2008; Yang, 2006). Recently, we have reported a few such compounds (Ban, 2010; Ban & Li, 2008a,b; Li & Ban, 2009a,b). We report here the crystal structure of the title new compound.

The asymmetric unit of the title hydrazone compound, Fig. 1, contains two independent molecules. The dihedral angles between the benzene ring and the pyridine ring in each molecule are 24.4 (6) and 23.7 (6)°, respectively. The molecules exist in a trans configuration with respect to the central methylidene units. In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1), forming chains along the a axis, Fig. 2.

Related literature top

For the biological activity of hydrazones, see: Zhong et al. (2007); Raj et al. (2007); Jimenez-Pulido et al. (2008). For related structures, see: Ban (2010); Ban & Li (2008a,b); Li & Ban (2009a,b); Yehye et al. (2008); Fun et al. (2008a,b); Yang et al. (2008); Ejsmont et al. (2008); Yang (2006).

Experimental top

The title compound was prepared by refluxing 5-bromo-2-methoxybenzaldehyde (1.0 mol, 0.22 g) with isonicotinohydrazide (1.0 mol, 0.14 g) in methanol (100 ml). Excess methanol was removed from the mixture by distillation. The colourless solid product was filtered, and washed three times with methanol. Colourless block-shaped crystals of the title compound were obtained from a methanol solution of the compound by slow evaporation in air.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 molecular structure of the title compound, showing 30% probability displacement ellipsoids for the non-hydrogen atoms. A hydrogen bond is shown as a dashed line.
	Fig. 2. The packing diagram of the title compound, viewed along the c axis. Hydrogen bonds are shown as dashed lines.

(E)-N'-(5-Bromo-2-methoxybenzylidene)isonicotinohydrazide top

Crystal data top

C₁₄H₁₂BrN₃O₂	F(000) = 1344
M_r = 334.18	D_x = 1.567 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 916 reflections
a = 10.020 (3) Å	θ = 2.5–24.3°
b = 25.732 (2) Å	µ = 2.91 mm⁻¹
c = 11.243 (2) Å	T = 298 K
β = 102.199 (3)°	Block, colourless
V = 2833.4 (10) Å³	0.13 × 0.10 × 0.10 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	5922 independent reflections
Radiation source: fine-focus sealed tube	2018 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.114
ω scans	θ_max = 27.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.704, T_max = 0.760	k = −15→32
14099 measured reflections	l = −12→14

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) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ²(F_o²)] where P = (F_o² + 2F_c²)/3
5922 reflections	(Δ/σ)_max < 0.001
369 parameters	Δρ_max = 0.32 e Å⁻³
2 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₁₄H₁₂BrN₃O₂	V = 2833.4 (10) Å³
M_r = 334.18	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.020 (3) Å	µ = 2.91 mm⁻¹
b = 25.732 (2) Å	T = 298 K
c = 11.243 (2) Å	0.13 × 0.10 × 0.10 mm
β = 102.199 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5922 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2018 reflections with I > 2σ(I)
T_min = 0.704, T_max = 0.760	R_int = 0.114
14099 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	2 restraints
wR(F²) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	Δρ_max = 0.32 e Å⁻³
5922 reflections	Δρ_min = −0.43 e Å⁻³
369 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
Br1	0.51353 (8)	0.35943 (3)	0.41403 (8)	0.0813 (3)
Br2	0.03344 (8)	−0.09381 (3)	0.49305 (8)	0.0786 (3)
N1	0.7533 (5)	0.1886 (2)	0.2601 (5)	0.0433 (14)
N2	0.7920 (5)	0.1410 (2)	0.2216 (5)	0.0483 (15)
N3	0.8554 (7)	−0.0399 (2)	0.0738 (5)	0.0570 (17)
N4	0.2636 (5)	0.0667 (2)	0.2875 (5)	0.0469 (15)
N5	0.3008 (5)	0.1126 (2)	0.2381 (5)	0.0455 (15)
N6	0.3357 (8)	0.2873 (2)	0.0375 (6)	0.070 (2)
O1	1.0434 (5)	0.29599 (17)	0.2924 (4)	0.0661 (14)
O2	0.5883 (5)	0.10295 (15)	0.2207 (4)	0.0531 (13)
O3	0.5607 (5)	−0.03865 (16)	0.3491 (4)	0.0627 (14)
O4	0.0906 (5)	0.14763 (16)	0.2208 (5)	0.0675 (15)
C1	0.8234 (7)	0.2757 (2)	0.3160 (6)	0.0396 (17)
C2	0.9269 (8)	0.3125 (3)	0.3234 (6)	0.0504 (19)
C3	0.9065 (7)	0.3632 (3)	0.3589 (6)	0.056 (2)
H3	0.9754	0.3878	0.3643	0.068*
C4	0.7825 (8)	0.3763 (3)	0.3859 (6)	0.056 (2)
H4	0.7671	0.4102	0.4087	0.068*
C5	0.6821 (7)	0.3396 (3)	0.3791 (6)	0.0478 (19)
C6	0.7036 (7)	0.2897 (3)	0.3450 (6)	0.0497 (19)
H6	0.6350	0.2651	0.3417	0.060*
C7	1.1577 (7)	0.3308 (3)	0.3069 (6)	0.070 (2)
H7A	1.1368	0.3586	0.2489	0.105*
H7B	1.2364	0.3123	0.2936	0.105*
H7C	1.1763	0.3449	0.3878	0.105*
C8	0.8473 (7)	0.2231 (2)	0.2755 (6)	0.054 (2)
H8	0.9325	0.2146	0.2606	0.064*
C9	0.7057 (7)	0.1007 (2)	0.2057 (6)	0.0432 (18)
C10	0.7624 (7)	0.0518 (2)	0.1629 (6)	0.0387 (17)
C11	0.6714 (7)	0.0151 (2)	0.1033 (6)	0.052 (2)
H11	0.5777	0.0201	0.0927	0.062*
C12	0.7233 (8)	−0.0294 (3)	0.0596 (6)	0.058 (2)
H12	0.6615	−0.0534	0.0177	0.069*
C13	0.9394 (7)	−0.0048 (3)	0.1323 (6)	0.055 (2)
H13	1.0325	−0.0113	0.1443	0.066*
C14	0.8989 (7)	0.0409 (2)	0.1769 (6)	0.0464 (18)
H14	0.9638	0.0644	0.2165	0.056*
C15	0.3380 (7)	−0.0171 (2)	0.3649 (6)	0.0431 (18)
C16	0.4437 (7)	−0.0535 (3)	0.3829 (6)	0.0456 (18)
C17	0.4289 (7)	−0.1015 (3)	0.4355 (6)	0.055 (2)
H17	0.4998	−0.1255	0.4484	0.066*
C18	0.3064 (8)	−0.1126 (3)	0.4681 (6)	0.057 (2)
H18	0.2953	−0.1445	0.5040	0.068*
C19	0.2015 (6)	−0.0777 (3)	0.4487 (6)	0.0452 (18)
C20	0.2170 (7)	−0.0301 (3)	0.3968 (6)	0.0473 (18)
H20	0.1450	−0.0065	0.3832	0.057*
C21	0.6772 (7)	−0.0721 (3)	0.3758 (6)	0.072 (2)
H21A	0.6994	−0.0793	0.4615	0.107*
H21B	0.7534	−0.0553	0.3525	0.107*
H21C	0.6571	−0.1040	0.3315	0.107*
C22	0.3574 (7)	0.0332 (3)	0.3104 (6)	0.0483 (19)
H22	0.4416	0.0407	0.2919	0.058*
C23	0.2085 (8)	0.1511 (2)	0.2091 (6)	0.0479 (19)
C24	0.2575 (7)	0.1983 (2)	0.1524 (6)	0.0398 (18)
C25	0.3935 (7)	0.2111 (3)	0.1626 (6)	0.059 (2)
H25	0.4620	0.1904	0.2077	0.071*
C26	0.4257 (8)	0.2552 (3)	0.1049 (7)	0.069 (2)
H26	0.5177	0.2632	0.1137	0.083*
C27	0.2071 (10)	0.2744 (3)	0.0269 (7)	0.073 (3)
H27	0.1409	0.2951	−0.0214	0.087*
C28	0.1643 (7)	0.2316 (3)	0.0838 (6)	0.053 (2)
H28	0.0714	0.2253	0.0755	0.064*
H5	0.388 (2)	0.116 (2)	0.232 (6)	0.080*
H2	0.880 (2)	0.139 (3)	0.214 (6)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0673 (6)	0.0816 (6)	0.0990 (7)	0.0128 (5)	0.0266 (5)	−0.0272 (6)
Br2	0.0568 (6)	0.0881 (7)	0.0920 (7)	−0.0143 (5)	0.0184 (5)	0.0230 (6)
N1	0.038 (4)	0.035 (3)	0.059 (4)	0.002 (3)	0.016 (3)	−0.003 (3)
N2	0.032 (3)	0.034 (3)	0.081 (4)	0.007 (3)	0.018 (3)	−0.001 (3)
N3	0.057 (4)	0.039 (4)	0.078 (5)	0.007 (4)	0.021 (4)	−0.002 (3)
N4	0.047 (4)	0.032 (3)	0.064 (4)	0.000 (3)	0.016 (3)	−0.002 (3)
N5	0.037 (4)	0.030 (3)	0.074 (4)	−0.001 (3)	0.022 (3)	0.007 (3)
N6	0.091 (6)	0.044 (4)	0.076 (5)	−0.012 (4)	0.021 (5)	0.000 (4)
O1	0.050 (3)	0.054 (3)	0.102 (4)	−0.018 (3)	0.032 (3)	−0.016 (3)
O2	0.042 (3)	0.033 (3)	0.090 (4)	−0.002 (2)	0.026 (3)	0.000 (2)
O3	0.050 (3)	0.049 (3)	0.096 (4)	0.013 (3)	0.028 (3)	0.011 (3)
O4	0.036 (3)	0.045 (3)	0.127 (5)	0.002 (3)	0.032 (3)	0.003 (3)
C1	0.038 (4)	0.034 (4)	0.051 (5)	−0.009 (4)	0.018 (4)	−0.004 (4)
C2	0.049 (5)	0.035 (5)	0.069 (6)	−0.007 (4)	0.018 (4)	−0.012 (4)
C3	0.058 (5)	0.040 (5)	0.074 (6)	−0.021 (4)	0.022 (4)	−0.002 (4)
C4	0.070 (6)	0.033 (4)	0.070 (6)	−0.007 (4)	0.022 (5)	−0.015 (4)
C5	0.051 (5)	0.047 (5)	0.044 (5)	0.002 (4)	0.006 (4)	0.001 (4)
C6	0.039 (5)	0.039 (5)	0.072 (6)	−0.008 (4)	0.014 (4)	−0.008 (4)
C7	0.043 (5)	0.078 (6)	0.094 (6)	−0.020 (4)	0.029 (4)	0.000 (5)
C8	0.053 (5)	0.034 (4)	0.077 (6)	−0.004 (4)	0.021 (4)	−0.011 (4)
C9	0.039 (5)	0.033 (4)	0.059 (5)	0.004 (4)	0.013 (4)	0.003 (4)
C10	0.035 (4)	0.031 (4)	0.055 (5)	0.003 (3)	0.020 (4)	0.007 (4)
C11	0.035 (4)	0.030 (4)	0.090 (6)	0.001 (4)	0.015 (4)	−0.004 (4)
C12	0.058 (6)	0.033 (5)	0.083 (6)	−0.004 (4)	0.018 (5)	0.000 (4)
C13	0.042 (5)	0.043 (5)	0.083 (6)	0.006 (4)	0.018 (4)	−0.003 (5)
C14	0.045 (5)	0.033 (4)	0.063 (5)	−0.002 (4)	0.017 (4)	−0.009 (4)
C15	0.040 (5)	0.033 (4)	0.058 (5)	0.003 (4)	0.015 (4)	−0.008 (4)
C16	0.053 (5)	0.034 (4)	0.053 (5)	−0.009 (4)	0.018 (4)	−0.005 (4)
C17	0.047 (5)	0.050 (5)	0.069 (6)	0.009 (4)	0.013 (4)	0.000 (4)
C18	0.067 (6)	0.042 (5)	0.058 (5)	0.000 (4)	0.008 (4)	0.003 (4)
C19	0.034 (4)	0.045 (5)	0.054 (5)	−0.005 (4)	0.004 (4)	0.006 (4)
C20	0.042 (5)	0.043 (5)	0.059 (5)	0.003 (4)	0.017 (4)	0.000 (4)
C21	0.053 (5)	0.079 (6)	0.085 (6)	0.033 (5)	0.020 (4)	−0.002 (5)
C22	0.046 (5)	0.041 (5)	0.063 (5)	0.001 (4)	0.023 (4)	0.000 (4)
C23	0.045 (5)	0.033 (5)	0.069 (5)	0.001 (4)	0.021 (4)	0.002 (4)
C24	0.039 (4)	0.028 (4)	0.052 (5)	0.000 (4)	0.008 (4)	−0.013 (4)
C25	0.052 (5)	0.048 (5)	0.078 (6)	−0.002 (4)	0.016 (4)	0.000 (5)
C26	0.062 (6)	0.052 (5)	0.092 (7)	−0.010 (5)	0.012 (5)	0.011 (5)
C27	0.106 (8)	0.046 (6)	0.063 (6)	0.013 (5)	0.011 (6)	0.015 (5)
C28	0.045 (5)	0.045 (5)	0.066 (5)	0.011 (4)	0.004 (4)	0.005 (4)

Geometric parameters (Å, º) top

Br1—C5	1.884 (7)	C8—H8	0.9300
Br2—C19	1.900 (6)	C9—C10	1.500 (8)
N1—C8	1.279 (7)	C10—C14	1.373 (8)
N1—N2	1.382 (6)	C10—C11	1.384 (8)
N2—C9	1.337 (8)	C11—C12	1.390 (8)
N2—H2	0.900 (10)	C11—H11	0.9300
N3—C13	1.313 (8)	C12—H12	0.9300
N3—C12	1.326 (8)	C13—C14	1.372 (8)
N4—C22	1.262 (7)	C13—H13	0.9300
N4—N5	1.388 (6)	C14—H14	0.9300
N5—C23	1.347 (8)	C15—C20	1.376 (8)
N5—H5	0.901 (10)	C15—C16	1.395 (8)
N6—C27	1.312 (9)	C15—C22	1.464 (8)
N6—C26	1.335 (8)	C16—C17	1.391 (8)
O1—C2	1.354 (8)	C17—C18	1.384 (9)
O1—C7	1.437 (7)	C17—H17	0.9300
O2—C9	1.224 (7)	C18—C19	1.364 (8)
O3—C16	1.361 (7)	C18—H18	0.9300
O3—C21	1.430 (7)	C19—C20	1.381 (8)
O4—C23	1.219 (7)	C20—H20	0.9300
C1—C6	1.358 (8)	C21—H21A	0.9600
C1—C2	1.394 (8)	C21—H21B	0.9600
C1—C8	1.463 (8)	C21—H21C	0.9600
C2—C3	1.392 (8)	C22—H22	0.9300
C3—C4	1.382 (9)	C23—C24	1.502 (8)
C3—H3	0.9300	C24—C28	1.377 (8)
C4—C5	1.371 (8)	C24—C25	1.383 (8)
C4—H4	0.9300	C25—C26	1.378 (9)
C5—C6	1.369 (8)	C25—H25	0.9300
C6—H6	0.9300	C26—H26	0.9300
C7—H7A	0.9600	C27—C28	1.386 (9)
C7—H7B	0.9600	C27—H27	0.9300
C7—H7C	0.9600	C28—H28	0.9300

C8—N1—N2	114.2 (5)	N3—C13—C14	124.4 (7)
C9—N2—N1	120.9 (5)	N3—C13—H13	117.8
C9—N2—H2	124 (4)	C14—C13—H13	117.8
N1—N2—H2	115 (4)	C13—C14—C10	119.9 (6)
C13—N3—C12	116.0 (6)	C13—C14—H14	120.1
C22—N4—N5	114.3 (6)	C10—C14—H14	120.1
C23—N5—N4	119.6 (6)	C20—C15—C16	118.9 (6)
C23—N5—H5	122 (4)	C20—C15—C22	121.7 (6)
N4—N5—H5	118 (4)	C16—C15—C22	119.3 (6)
C27—N6—C26	115.3 (7)	O3—C16—C17	122.9 (6)
C2—O1—C7	119.0 (5)	O3—C16—C15	116.4 (6)
C16—O3—C21	119.1 (5)	C17—C16—C15	120.7 (7)
C6—C1—C2	119.3 (6)	C18—C17—C16	118.5 (7)
C6—C1—C8	122.2 (6)	C18—C17—H17	120.7
C2—C1—C8	118.6 (6)	C16—C17—H17	120.7
O1—C2—C3	123.7 (6)	C19—C18—C17	121.1 (7)
O1—C2—C1	116.3 (6)	C19—C18—H18	119.4
C3—C2—C1	120.1 (7)	C17—C18—H18	119.4
C4—C3—C2	119.1 (6)	C18—C19—C20	120.0 (6)
C4—C3—H3	120.4	C18—C19—Br2	120.7 (6)
C2—C3—H3	120.4	C20—C19—Br2	119.3 (5)
C5—C4—C3	120.1 (6)	C15—C20—C19	120.6 (6)
C5—C4—H4	120.0	C15—C20—H20	119.7
C3—C4—H4	120.0	C19—C20—H20	119.7
C6—C5—C4	120.4 (6)	O3—C21—H21A	109.5
C6—C5—Br1	120.9 (6)	O3—C21—H21B	109.5
C4—C5—Br1	118.7 (6)	H21A—C21—H21B	109.5
C1—C6—C5	121.1 (6)	O3—C21—H21C	109.5
C1—C6—H6	119.5	H21A—C21—H21C	109.5
C5—C6—H6	119.5	H21B—C21—H21C	109.5
O1—C7—H7A	109.5	N4—C22—C15	122.1 (6)
O1—C7—H7B	109.5	N4—C22—H22	119.0
H7A—C7—H7B	109.5	C15—C22—H22	119.0
O1—C7—H7C	109.5	O4—C23—N5	123.5 (6)
H7A—C7—H7C	109.5	O4—C23—C24	121.0 (6)
H7B—C7—H7C	109.5	N5—C23—C24	115.4 (6)
N1—C8—C1	121.3 (6)	C28—C24—C25	115.9 (6)
N1—C8—H8	119.4	C28—C24—C23	119.8 (6)
C1—C8—H8	119.4	C25—C24—C23	124.3 (6)
O2—C9—N2	123.9 (6)	C26—C25—C24	118.8 (7)
O2—C9—C10	121.6 (6)	C26—C25—H25	120.6
N2—C9—C10	114.5 (6)	C24—C25—H25	120.6
C14—C10—C11	117.0 (6)	N6—C26—C25	125.5 (8)
C14—C10—C9	124.8 (6)	N6—C26—H26	117.3
C11—C10—C9	118.2 (6)	C25—C26—H26	117.3
C10—C11—C12	118.4 (6)	N6—C27—C28	123.6 (7)
C10—C11—H11	120.8	N6—C27—H27	118.2
C12—C11—H11	120.8	C28—C27—H27	118.2
N3—C12—C11	124.3 (7)	C24—C28—C27	120.9 (7)
N3—C12—H12	117.9	C24—C28—H28	119.5
C11—C12—H12	117.9	C27—C28—H28	119.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O2	0.90 (1)	2.06 (2)	2.939 (7)	164 (6)
N2—H2···O4ⁱ	0.90 (1)	2.11 (2)	2.999 (7)	168 (6)

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂BrN₃O₂
M_r	334.18
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.020 (3), 25.732 (2), 11.243 (2)
β (°)	102.199 (3)
V (Å³)	2833.4 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.91
Crystal size (mm)	0.13 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.704, 0.760
No. of measured, independent and observed [I > 2σ(I)] reflections	14099, 5922, 2018
R_int	0.114
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.143, 0.94
No. of reflections	5922
No. of parameters	369
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.43

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), 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
N5—H5···O2	0.901 (10)	2.06 (2)	2.939 (7)	164 (6)
N2—H2···O4ⁱ	0.900 (10)	2.113 (18)	2.999 (7)	168 (6)

Symmetry code: (i) x+1, y, z.

Acknowledgements

The authors acknowledge the support of the Youth Foundation of the University of Science and Technology Liaoning (2010Y06) and the Natural Science Foundation of Liaoning Province (20102157).

References

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