(E)-N′-[1-(4-Bromo­phen­yl)ethyl­idene]benzohydrazide

Wang, H.-Y.; Fan, C.-G.; Yang, Z.-N.

doi:10.1107/S1600536809049952

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o1

doi:10.1107/S1600536809049952

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(E)-N′-[1-(4-Bromophenyl)ethylidene]benzohydrazide

Hong-Yun Wang,^a Chuan-Gang Fan ^a ^* and Zhong-Nian Yang ^a

^aCollege of Chemistry and Chemical Technology, Binzhou University, Binzhou 256600, Shandong, People's Republic of China
^*Correspondence e-mail: fanchuangang2009@163.com

(Received 30 October 2009; accepted 20 November 2009; online 4 December 2009)

The asymmetric unit of the title compound, C₁₅H₁₃BrN₂O, contains two independent molecules with different conformations; the two aromatic rings form dihedral angles of 32.4 (4) and 27.5 (4)° in the two molecules. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link molecules into chains propagating in [100].

Related literature

For the biological properties of Schiff base ligands, see: Chakraborty & Patel (1996 ); Jeewoth et al.(1999 ). For related crystal structures, see: Fun et al. (2008 ); Cui et al. (2009 ); Nie (2008 ).

Experimental

Crystal data

C₁₅H₁₃BrN₂O
M_r = 317.18
Monoclinic, P 2₁ /c
a = 9.9770 (11) Å
b = 31.487 (3) Å
c = 8.7613 (9) Å
β = 96.1040 (10)°
V = 2736.8 (5) Å³
Z = 8
Mo Kα radiation
μ = 3.00 mm⁻¹
T = 298 K
0.49 × 0.18 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.321, T_max = 0.715
13558 measured reflections
4804 independent reflections
1961 reflections with I > 2σ(I)
R_int = 0.079

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.189
S = 1.02
4804 reflections
345 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1ⁱ	0.86	2.20	2.943 (8)	144
N1—H1⋯O2	0.86	2.23	3.000 (8)	149
Symmetry code: (i) x+1, y, z.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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/S1600536809049952/cv2651sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809049952/cv2651Isup2.hkl

checkCIF report

Comment top

Schiff base compounds are known as having strong anticancer activity (Chakraborty & Patel, 1996) and various biological properties (Jeewoth et al., 1999). Herewith we present the title compound (I) - a new Shiff base compound.

In (I) (Fig. 1), the bond lengths an angles are normal and are comparable to the values observed in similar compounds (Nie et al., 2008; Fun et al., 2008; Cui et al., 2009). The asymmetric unit of (I), contains two independent molecules A and B, respectively. In molecule A, two aromatic rings form a dihedral angle of 32.4 (4) °, while in molecule B this angle is 27.5 (4) °. The C=N bond lengths in the molecules are 1.293 (9)° and 1.272 (9)° (C9=N2,C24=N4), showing the double-bond character.

Weak intermolecular N—H···O hydrogen bonds (Table 1) link molecules into one-dimensional chain propagated in direction [100].

Related literature top

For the biological properties of Schiff base ligands, see: Chakraborty & Patel (1996); Jeewoth et al.(1999). For related crystal structures, see: Fun et al. (2008); Cui et al. (2009); Nie (2008).

Experimental top

Benzohydrazide (5.0 mmol), 20 ml e thanol and 4-bromoacetophenone (5.0 mmol) were mixed in 50 ml flash. After refluxing 3 h, the resulting mixture was cooled to room temperature, and recrystalized from ethanol, and afforded the title compound as a crystalline solid. Elemental analysis: calculated for C₁₅H₁₃BrN₂O: C 56.80, H 4.13, N 8.83%; found: C 56.78, H 4.24, N 8.69%.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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. A view of (I) showing the atomic numbering scheme and 30% probability displacement ellipsoids.

(E)-N'-[1-(4-Bromophenyl)ethylidene]benzohydrazide top

Crystal data top

C₁₅H₁₃BrN₂O	F(000) = 1280
M_r = 317.18	D_x = 1.540 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.9770 (11) Å	Cell parameters from 1649 reflections
b = 31.487 (3) Å	θ = 2.6–22.4°
c = 8.7613 (9) Å	µ = 3.00 mm⁻¹
β = 96.104 (1)°	T = 298 K
V = 2736.8 (5) Å³	Block, colourless
Z = 8	0.49 × 0.18 × 0.12 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4804 independent reflections
Radiation source: fine-focus sealed tube	1961 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.079
phi and ω scans	θ_max = 25.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→10
T_min = 0.321, T_max = 0.715	k = −37→37
13558 measured reflections	l = −9→10

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) = 0.189	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0544P)² + 6.194P] where P = (F_o² + 2F_c²)/3
4804 reflections	(Δ/σ)_max < 0.001
345 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₁₅H₁₃BrN₂O	V = 2736.8 (5) Å³
M_r = 317.18	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.9770 (11) Å	µ = 3.00 mm⁻¹
b = 31.487 (3) Å	T = 298 K
c = 8.7613 (9) Å	0.49 × 0.18 × 0.12 mm
β = 96.104 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4804 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1961 reflections with I > 2σ(I)
T_min = 0.321, T_max = 0.715	R_int = 0.079
13558 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.189	H-atom parameters constrained
S = 1.02	Δρ_max = 0.47 e Å⁻³
4804 reflections	Δρ_min = −0.44 e Å⁻³
345 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	0.05576 (10)	0.04761 (3)	0.12825 (13)	0.0742 (4)
Br2	0.53233 (12)	0.04532 (3)	0.13223 (14)	0.0925 (5)
N1	0.1623 (6)	0.30472 (16)	0.1860 (7)	0.0375 (17)
H1	0.2450	0.3123	0.2070	0.045*
N2	0.1275 (6)	0.26193 (18)	0.1697 (8)	0.0414 (18)
N3	0.6642 (6)	0.30098 (17)	0.1957 (7)	0.0415 (18)
H3	0.7454	0.3084	0.2272	0.050*
N4	0.6303 (6)	0.25836 (18)	0.1760 (7)	0.0375 (17)
O1	−0.0567 (5)	0.32437 (15)	0.1524 (7)	0.0512 (16)
O2	0.4486 (5)	0.32125 (15)	0.1277 (6)	0.0465 (15)
C1	0.0627 (8)	0.3340 (2)	0.1678 (9)	0.037 (2)
C2	0.1063 (8)	0.3795 (2)	0.1712 (9)	0.036 (2)
C3	0.2317 (9)	0.3936 (3)	0.2308 (11)	0.056 (3)
H3A	0.2965	0.3740	0.2693	0.067*
C4	0.2627 (9)	0.4362 (3)	0.2342 (13)	0.077 (3)
H4	0.3476	0.4454	0.2750	0.092*
C5	0.1660 (12)	0.4652 (3)	0.1765 (13)	0.084 (4)
H5	0.1857	0.4941	0.1776	0.100*
C6	0.0444 (10)	0.4515 (3)	0.1191 (11)	0.066 (3)
H6	−0.0198	0.4711	0.0792	0.079*
C7	0.0123 (8)	0.4089 (2)	0.1179 (10)	0.052 (2)
H7	−0.0741	0.4002	0.0806	0.063*
C8	0.3318 (7)	0.2479 (2)	0.3464 (9)	0.039 (2)
H8A	0.4062	0.2526	0.2873	0.058*
H8B	0.3543	0.2257	0.4196	0.058*
H8C	0.3132	0.2736	0.3996	0.058*
C9	0.2105 (7)	0.2354 (2)	0.2421 (9)	0.032 (2)
C10	0.1756 (7)	0.1897 (2)	0.2133 (9)	0.034 (2)
C11	0.2275 (8)	0.1584 (2)	0.3126 (9)	0.041 (2)
H11	0.2867	0.1656	0.3979	0.049*
C12	0.1921 (8)	0.1161 (2)	0.2866 (10)	0.045 (2)
H12	0.2287	0.0953	0.3537	0.053*
C13	0.1045 (8)	0.1051 (2)	0.1637 (10)	0.036 (2)
C14	0.0528 (8)	0.1356 (2)	0.0611 (10)	0.046 (2)
H14	−0.0047	0.1281	−0.0253	0.055*
C15	0.0875 (7)	0.1777 (2)	0.0884 (9)	0.036 (2)
H15	0.0505	0.1984	0.0210	0.044*
C16	0.5674 (8)	0.3303 (2)	0.1644 (9)	0.0331 (19)
C17	0.6123 (7)	0.3751 (2)	0.1748 (10)	0.037 (2)
C18	0.5576 (8)	0.4041 (2)	0.0657 (10)	0.051 (2)
H18	0.4952	0.3948	−0.0137	0.061*
C19	0.5939 (10)	0.4464 (3)	0.0728 (13)	0.074 (3)
H19	0.5593	0.4653	−0.0029	0.089*
C20	0.6835 (10)	0.4602 (3)	0.1961 (14)	0.073 (3)
H20	0.7081	0.4887	0.2034	0.088*
C21	0.7347 (10)	0.4324 (3)	0.3050 (13)	0.071 (3)
H21	0.7933	0.4420	0.3874	0.085*
C22	0.7009 (8)	0.3897 (3)	0.2950 (11)	0.056 (3)
H22	0.7380	0.3709	0.3695	0.068*
C23	0.8370 (8)	0.2420 (2)	0.3406 (11)	0.052 (2)
H23A	0.9101	0.2458	0.2791	0.077*
H23B	0.8582	0.2194	0.4125	0.077*
H23C	0.8231	0.2678	0.3953	0.077*
C24	0.7126 (7)	0.2313 (2)	0.2401 (9)	0.034 (2)
C25	0.6731 (8)	0.1857 (2)	0.2140 (9)	0.036 (2)
C26	0.7538 (8)	0.1525 (2)	0.2651 (11)	0.057 (3)
H26	0.8374	0.1581	0.3188	0.068*
C27	0.7146 (10)	0.1107 (3)	0.2391 (12)	0.065 (3)
H27	0.7719	0.0886	0.2734	0.078*
C28	0.5913 (10)	0.1022 (3)	0.1627 (11)	0.058 (3)
C29	0.5083 (9)	0.1343 (3)	0.1057 (10)	0.057 (3)
H29	0.4250	0.1285	0.0518	0.069*
C30	0.5519 (8)	0.1757 (3)	0.1305 (10)	0.057 (3)
H30	0.4973	0.1977	0.0892	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0932 (8)	0.0335 (5)	0.0912 (9)	−0.0095 (5)	−0.0117 (6)	−0.0017 (5)
Br2	0.1330 (11)	0.0416 (6)	0.1011 (11)	−0.0177 (6)	0.0043 (8)	−0.0026 (6)
N1	0.032 (4)	0.021 (3)	0.058 (5)	−0.003 (3)	0.001 (3)	−0.001 (3)
N2	0.033 (4)	0.028 (3)	0.063 (6)	−0.002 (3)	0.005 (4)	0.004 (3)
N3	0.032 (4)	0.027 (3)	0.064 (6)	0.000 (3)	−0.002 (4)	0.001 (3)
N4	0.035 (4)	0.037 (4)	0.041 (5)	−0.003 (3)	0.005 (4)	0.001 (3)
O1	0.034 (3)	0.038 (3)	0.083 (5)	−0.005 (3)	0.008 (3)	−0.003 (3)
O2	0.028 (3)	0.038 (3)	0.072 (5)	−0.004 (2)	0.000 (3)	−0.004 (3)
C1	0.031 (5)	0.035 (4)	0.045 (6)	−0.001 (4)	0.006 (4)	0.000 (4)
C2	0.036 (5)	0.034 (4)	0.040 (6)	0.000 (4)	0.008 (4)	0.000 (4)
C3	0.045 (6)	0.046 (5)	0.075 (8)	0.003 (4)	0.000 (5)	−0.018 (5)
C4	0.045 (6)	0.048 (6)	0.137 (11)	−0.015 (5)	0.006 (6)	−0.030 (6)
C5	0.096 (9)	0.037 (6)	0.123 (11)	−0.003 (6)	0.036 (8)	0.001 (6)
C6	0.067 (7)	0.033 (5)	0.099 (9)	0.001 (5)	0.019 (6)	0.008 (5)
C7	0.050 (5)	0.036 (5)	0.072 (7)	0.005 (4)	0.006 (5)	0.010 (4)
C8	0.043 (5)	0.033 (4)	0.039 (6)	−0.006 (4)	−0.003 (4)	0.003 (4)
C9	0.034 (5)	0.029 (4)	0.035 (6)	0.001 (3)	0.005 (4)	0.008 (4)
C10	0.033 (5)	0.032 (4)	0.036 (6)	0.002 (3)	0.005 (4)	0.005 (4)
C11	0.045 (5)	0.039 (4)	0.037 (6)	−0.003 (4)	−0.004 (4)	−0.004 (4)
C12	0.054 (6)	0.034 (4)	0.044 (6)	−0.005 (4)	−0.004 (5)	0.014 (4)
C13	0.045 (5)	0.021 (4)	0.044 (6)	−0.002 (3)	0.008 (4)	0.002 (4)
C14	0.051 (6)	0.039 (5)	0.044 (6)	−0.011 (4)	−0.003 (4)	−0.003 (4)
C15	0.041 (5)	0.036 (4)	0.032 (6)	0.001 (4)	0.003 (4)	0.009 (4)
C16	0.035 (5)	0.032 (4)	0.033 (6)	−0.002 (4)	0.008 (4)	−0.009 (4)
C17	0.033 (5)	0.038 (4)	0.042 (6)	0.003 (4)	0.015 (4)	−0.010 (4)
C18	0.052 (6)	0.040 (5)	0.059 (7)	−0.003 (4)	−0.001 (5)	0.005 (4)
C19	0.085 (8)	0.031 (5)	0.108 (10)	−0.006 (5)	0.018 (7)	0.001 (5)
C20	0.075 (8)	0.035 (5)	0.114 (11)	−0.010 (5)	0.031 (7)	−0.024 (6)
C21	0.064 (7)	0.055 (6)	0.094 (9)	−0.016 (5)	0.012 (6)	−0.036 (6)
C22	0.043 (6)	0.058 (6)	0.068 (7)	0.002 (4)	0.004 (5)	−0.015 (5)
C23	0.035 (5)	0.048 (5)	0.070 (7)	0.000 (4)	−0.002 (5)	0.000 (5)
C24	0.024 (5)	0.043 (5)	0.036 (6)	0.005 (4)	0.015 (4)	−0.002 (4)
C25	0.035 (5)	0.033 (4)	0.042 (6)	0.007 (4)	0.010 (4)	0.007 (4)
C26	0.046 (6)	0.042 (5)	0.081 (8)	0.005 (4)	0.001 (5)	0.009 (5)
C27	0.070 (7)	0.035 (5)	0.090 (9)	0.013 (5)	0.007 (6)	0.005 (5)
C28	0.064 (7)	0.042 (5)	0.070 (8)	−0.001 (5)	0.008 (6)	−0.005 (5)
C29	0.054 (6)	0.051 (5)	0.065 (7)	−0.006 (5)	−0.003 (5)	−0.013 (5)
C30	0.050 (6)	0.049 (5)	0.071 (8)	0.003 (4)	−0.004 (5)	−0.004 (5)

Geometric parameters (Å, º) top

Br1—C13	1.891 (7)	C12—C13	1.358 (10)
Br2—C28	1.895 (8)	C12—H12	0.9300
N1—C1	1.353 (9)	C13—C14	1.379 (10)
N1—N2	1.395 (7)	C14—C15	1.382 (9)
N1—H1	0.8600	C14—H14	0.9300
N2—C9	1.293 (9)	C15—H15	0.9300
N3—C16	1.343 (8)	C16—C17	1.481 (9)
N3—N4	1.390 (7)	C17—C22	1.380 (11)
N3—H3	0.8600	C17—C18	1.390 (10)
N4—C24	1.272 (9)	C18—C19	1.380 (10)
O1—C1	1.223 (8)	C18—H18	0.9300
O2—C16	1.228 (8)	C19—C20	1.396 (13)
C1—C2	1.496 (9)	C19—H19	0.9300
C2—C7	1.366 (10)	C20—C21	1.356 (13)
C2—C3	1.376 (10)	C20—H20	0.9300
C3—C4	1.378 (10)	C21—C22	1.385 (11)
C3—H3A	0.9300	C21—H21	0.9300
C4—C5	1.384 (13)	C22—H22	0.9300
C4—H4	0.9300	C23—C24	1.482 (10)
C5—C6	1.334 (12)	C23—H23A	0.9600
C5—H5	0.9300	C23—H23B	0.9600
C6—C7	1.380 (10)	C23—H23C	0.9600
C6—H6	0.9300	C24—C25	1.498 (10)
C7—H7	0.9300	C25—C26	1.367 (10)
C8—C9	1.490 (10)	C25—C30	1.382 (10)
C8—H8A	0.9600	C26—C27	1.385 (11)
C8—H8B	0.9600	C26—H26	0.9300
C8—H8C	0.9600	C27—C28	1.363 (12)
C9—C10	1.496 (9)	C27—H27	0.9300
C10—C11	1.380 (9)	C28—C29	1.368 (11)
C10—C15	1.382 (10)	C29—C30	1.385 (10)
C11—C12	1.388 (9)	C29—H29	0.9300
C11—H11	0.9300	C30—H30	0.9300

C1—N1—N2	118.4 (6)	C15—C14—H14	120.5
C1—N1—H1	120.8	C14—C15—C10	121.8 (7)
N2—N1—H1	120.8	C14—C15—H15	119.1
C9—N2—N1	115.7 (6)	C10—C15—H15	119.1
C16—N3—N4	118.5 (6)	O2—C16—N3	123.3 (6)
C16—N3—H3	120.7	O2—C16—C17	120.9 (7)
N4—N3—H3	120.7	N3—C16—C17	115.8 (7)
C24—N4—N3	117.1 (6)	C22—C17—C18	118.6 (7)
O1—C1—N1	122.6 (7)	C22—C17—C16	122.0 (8)
O1—C1—C2	121.2 (7)	C18—C17—C16	119.3 (8)
N1—C1—C2	116.2 (7)	C19—C18—C17	121.4 (9)
C7—C2—C3	118.3 (7)	C19—C18—H18	119.3
C7—C2—C1	117.0 (7)	C17—C18—H18	119.3
C3—C2—C1	124.6 (7)	C18—C19—C20	118.6 (9)
C4—C3—C2	121.0 (8)	C18—C19—H19	120.7
C4—C3—H3A	119.5	C20—C19—H19	120.7
C2—C3—H3A	119.5	C21—C20—C19	120.4 (9)
C3—C4—C5	119.2 (9)	C21—C20—H20	119.8
C3—C4—H4	120.4	C19—C20—H20	119.8
C5—C4—H4	120.4	C20—C21—C22	120.7 (10)
C6—C5—C4	119.7 (9)	C20—C21—H21	119.6
C6—C5—H5	120.1	C22—C21—H21	119.6
C4—C5—H5	120.1	C17—C22—C21	120.3 (9)
C5—C6—C7	121.2 (9)	C17—C22—H22	119.9
C5—C6—H6	119.4	C21—C22—H22	119.9
C7—C6—H6	119.4	C24—C23—H23A	109.5
C2—C7—C6	120.5 (8)	C24—C23—H23B	109.5
C2—C7—H7	119.8	H23A—C23—H23B	109.5
C6—C7—H7	119.8	C24—C23—H23C	109.5
C9—C8—H8A	109.5	H23A—C23—H23C	109.5
C9—C8—H8B	109.5	H23B—C23—H23C	109.5
H8A—C8—H8B	109.5	N4—C24—C23	124.7 (7)
C9—C8—H8C	109.5	N4—C24—C25	115.3 (7)
H8A—C8—H8C	109.5	C23—C24—C25	119.9 (7)
H8B—C8—H8C	109.5	C26—C25—C30	116.8 (7)
N2—C9—C8	124.5 (6)	C26—C25—C24	123.2 (8)
N2—C9—C10	114.4 (7)	C30—C25—C24	120.0 (7)
C8—C9—C10	121.1 (6)	C25—C26—C27	121.9 (9)
C11—C10—C15	117.8 (7)	C25—C26—H26	119.0
C11—C10—C9	121.2 (7)	C27—C26—H26	119.0
C15—C10—C9	121.0 (7)	C28—C27—C26	119.4 (8)
C10—C11—C12	120.7 (8)	C28—C27—H27	120.3
C10—C11—H11	119.7	C26—C27—H27	120.3
C12—C11—H11	119.7	C27—C28—C29	121.0 (8)
C13—C12—C11	120.5 (7)	C27—C28—Br2	120.3 (7)
C13—C12—H12	119.8	C29—C28—Br2	118.7 (7)
C11—C12—H12	119.8	C28—C29—C30	118.2 (8)
C12—C13—C14	120.2 (7)	C28—C29—H29	120.9
C12—C13—Br1	120.5 (6)	C30—C29—H29	120.9
C14—C13—Br1	119.3 (6)	C25—C30—C29	122.7 (8)
C13—C14—C15	119.1 (8)	C25—C30—H30	118.7
C13—C14—H14	120.5	C29—C30—H30	118.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1ⁱ	0.86	2.20	2.943 (8)	144
N1—H1···O2	0.86	2.23	3.000 (8)	149

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃BrN₂O
M_r	317.18
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	9.9770 (11), 31.487 (3), 8.7613 (9)
β (°)	96.104 (1)
V (Å³)	2736.8 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.00
Crystal size (mm)	0.49 × 0.18 × 0.12

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.321, 0.715
No. of measured, independent and observed [I > 2σ(I)] reflections	13558, 4804, 1961
R_int	0.079
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.189, 1.02
No. of reflections	4804
No. of parameters	345
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.44

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), 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
N3—H3···O1ⁱ	0.86	2.20	2.943 (8)	144.1
N1—H1···O2	0.86	2.23	3.000 (8)	148.5

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

Acknowledgements

The authors acknowledge the financial support of the Foundation of Binzhou University.

References

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