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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 5| May 2012| Page o1304

(E)-N′-(5-Bromo-2-hy­dr­oxy­benzyl­­idene)-4-(di­methyl­amino)­benzohydrazide

aZibo Vocational Institute, Zibo 255314, People's Republic of China
*Correspondence e-mail: enyuwei@163.com

(Received 29 March 2012; accepted 30 March 2012; online 4 April 2012)

The title compound, C16H16BrN3O2, crystallized with two independent molcules in the asymmetric unit. Each mol­ecule has an E conformation about the C=N bond and the dihedral angles between the benzene rings are 30.5 (3) and 28.7 (3)°. In each mol­ecule, there is an O—H⋯N hydrogen bond and the two mol­ecules are linked by an N—H⋯O hydrogen bond. In the crystal, mol­ecules are further linked via N—H⋯O hydrogen bonds into chains propagating along [001].

Related literature

For further details concerning benzohydrazone compounds, see: Wang et al. (2012[Wang, D.-Y., Meng, X.-F. & Ma, J.-J. (2012). Acta Cryst. E68, o21.]); Horkaew et al. (2012[Horkaew, J., Chantrapromma, S., Anantapong, T., Kanjana-Opas, A. & Fun, H.-K. (2012). Acta Cryst. E68, o1069-o1070.]); Li (2011a[Li, X.-Y. (2011a). Acta Cryst. E67, o1798.],b[Li, X.-Y. (2011b). Acta Cryst. E67, o2511.], 2012[Li, X.-Y. (2012). Acta Cryst. E68, o696.]).

[Scheme 1]

Experimental

Crystal data
  • C16H16BrN3O2

  • Mr = 362.23

  • Monoclinic, C 2/c

  • a = 35.3800 (12) Å

  • b = 10.452 (1) Å

  • c = 18.5070 (15) Å

  • β = 111.463 (2)°

  • V = 6369.1 (8) Å3

  • Z = 16

  • Mo Kα radiation

  • μ = 2.59 mm−1

  • T = 298 K

  • 0.20 × 0.20 × 0.18 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.625, Tmax = 0.653

  • 25287 measured reflections

  • 6931 independent reflections

  • 2320 reflections with I > 2σ(I)

  • Rint = 0.168

Refinement
  • R[F2 > 2σ(F2)] = 0.065

  • wR(F2) = 0.197

  • S = 0.94

  • 6931 reflections

  • 411 parameters

  • 3 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.70 e Å−3

  • Δρmin = −0.44 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯N1 0.85 (1) 1.78 (3) 2.570 (7) 153 (7)
O3—H3A⋯N4 0.82 1.87 2.588 (7) 146
N2—H2⋯O4 0.90 (1) 2.04 (2) 2.920 (6) 166 (6)
N5—H5⋯O2i 0.90 (1) 1.95 (3) 2.807 (7) 160 (6)
Symmetry code: (i) [x, -y+1, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Continuing our work on the preparation (E)-N'-(5-Bromo-2-hydroxybenzylidene)-4-(dimethylamino)benzohydrazideof benzohydrazone compounds, the new title compound was synthesized and we report herein on its crystal structure.

The asymmetric unit of the title compound contains two independent molecules (A and B), Fig. 1. Each molecule has an E conformation about the CN bond. In molecule A the dihedral angle between the C1–C6 and C9–C14 benzene rings is 30.5 (3)°. In molecule B the dihedral angle between the benzene rings C17–C22 and C25–C30 is 28.7 (3)°. The bond lengths are within normal values when compared with those observed in the similar compounds (Wang et al., 2012; Horkaew et al., 2012; Li, 2011a,b; Li, 2012). In each molecule there is an O-H···N hydrogen bond , and the two indpendent molecules are linked by an N-H···O hydrogen bond (Table 1 and Fig. 1).

In the crystal, molecules are linked through N–H···O hydrogen bonds to form chains propagating along the c axis direction (Table 1 and Fig. 2).

Related literature top

For further details concerning benzohydrazone compounds, see: Wang et al. (2012); Horkaew et al. (2012); Li (2011a,b, 2012).

Experimental top

A mixture of 5-bromosalicylaldehyde (0.201 g, 1 mmol) and 4-dimethylaminobenzohydrazide (0.179 g, 1 mmol), and a few drops of acetic acid, were mixed and refluxed in 20 ml ethanol for 30 min. The reaction mixture was then cooled slowly to room temperature. Colourless block-like crystals of the title compound, suitable for X-ray analysis, were formed by slow evaporation of the solution.

Refinement top

The H atoms H1, H2, and H5 were located from a difference Fourier map and were freely refined. The remaining H-atoms were positioned geometrically and refined using a riding model: O–H = 0.82 Å, C–H = 0.93 and 0.96 Å, for CH and CH3 H atoms, respectively, with Uiso(H) = k × Ueq(O,C) where k = 1.5 for and OH and CH3 H atoms, and = 1.2 for other H atoms.

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
[Figure 1] Fig. 1. The molecular structure of the two indpendent molecules (A and B) of the title compound, showing the atom labelling. The displacement ellipsoids are drawn at the 30% probability level. Hydrogen bonds are drawn as dashed lines (see Table 1 for details).
[Figure 2] Fig. 2. Crystal packing diagram of the title compound, viewed along the b axis. Hydrogen bonds are drawn as dashed lines (see Table 1 for details; C bound H atoms have been omitted for clarity).
(E)-N'-(5-Bromo-2-hydroxybenzylidene)- 4-(dimethylamino)benzohydrazide top
Crystal data top
C16H16BrN3O2F(000) = 2944
Mr = 362.23Dx = 1.511 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1759 reflections
a = 35.3800 (12) Åθ = 2.3–24.3°
b = 10.452 (1) ŵ = 2.59 mm1
c = 18.5070 (15) ÅT = 298 K
β = 111.463 (2)°Block, colourless
V = 6369.1 (8) Å30.20 × 0.20 × 0.18 mm
Z = 16
Data collection top
Bruker SMART CCD area-detector
diffractometer
6931 independent reflections
Radiation source: fine-focus sealed tube2320 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.168
ω scansθmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 4345
Tmin = 0.625, Tmax = 0.653k = 1312
25287 measured reflectionsl = 2323
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.197H atoms treated by a mixture of independent and constrained refinement
S = 0.94 w = 1/[σ2(Fo2) + (0.0705P)2]
where P = (Fo2 + 2Fc2)/3
6931 reflections(Δ/σ)max < 0.001
411 parametersΔρmax = 0.70 e Å3
3 restraintsΔρmin = 0.44 e Å3
Crystal data top
C16H16BrN3O2V = 6369.1 (8) Å3
Mr = 362.23Z = 16
Monoclinic, C2/cMo Kα radiation
a = 35.3800 (12) ŵ = 2.59 mm1
b = 10.452 (1) ÅT = 298 K
c = 18.5070 (15) Å0.20 × 0.20 × 0.18 mm
β = 111.463 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
6931 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2320 reflections with I > 2σ(I)
Tmin = 0.625, Tmax = 0.653Rint = 0.168
25287 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0653 restraints
wR(F2) = 0.197H atoms treated by a mixture of independent and constrained refinement
S = 0.94Δρmax = 0.70 e Å3
6931 reflectionsΔρmin = 0.44 e Å3
411 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
xyzUiso*/Ueq
Br10.05924 (3)0.17985 (8)0.26798 (6)0.1074 (4)
O10.09419 (15)0.3023 (6)0.4577 (3)0.0859 (16)
O20.19862 (13)0.4457 (4)0.5806 (2)0.0575 (12)
N10.16745 (16)0.2904 (5)0.4615 (3)0.0483 (14)
N20.20495 (17)0.3485 (5)0.4771 (3)0.0488 (14)
N30.34499 (18)0.7781 (5)0.5532 (3)0.0642 (16)
C10.1174 (2)0.1398 (6)0.3926 (3)0.0457 (16)
C20.0872 (2)0.1945 (7)0.4124 (4)0.0616 (19)
C30.0489 (3)0.1427 (9)0.3884 (4)0.081 (2)
H30.02850.18290.40050.097*
C40.0410 (2)0.0325 (9)0.3468 (4)0.078 (2)
H40.01530.00460.33190.094*
C50.0707 (3)0.0244 (7)0.3268 (4)0.067 (2)
C60.1089 (2)0.0274 (6)0.3481 (4)0.0601 (19)
H60.12860.01120.33330.072*
C70.15762 (19)0.1970 (6)0.4126 (4)0.0487 (17)
H70.17570.16680.39070.058*
C80.2167 (2)0.4381 (6)0.5350 (4)0.0462 (16)
C90.25160 (19)0.5209 (6)0.5393 (3)0.0421 (15)
C100.27268 (19)0.5113 (6)0.4902 (3)0.0473 (16)
H100.26590.44640.45330.057*
C110.30347 (19)0.5941 (6)0.4937 (3)0.0513 (17)
H110.31720.58360.45990.062*
C120.31442 (19)0.6953 (6)0.5485 (4)0.0468 (16)
C130.2933 (2)0.7025 (6)0.5984 (4)0.0570 (19)
H130.30030.76560.63650.068*
C140.2622 (2)0.6194 (6)0.5936 (4)0.0540 (18)
H140.24820.62940.62700.065*
C150.3659 (2)0.7698 (7)0.5001 (5)0.088 (3)
H15A0.37930.68850.50600.132*
H15B0.38560.83720.51080.132*
H15C0.34670.77810.44790.132*
C160.3560 (2)0.8819 (6)0.6096 (4)0.082 (2)
H16A0.33240.93230.60370.123*
H16B0.37620.93480.60120.123*
H16C0.36680.84700.66120.123*
Br20.01643 (2)0.70242 (8)0.01969 (5)0.0909 (4)
O30.10533 (15)0.3944 (4)0.2737 (3)0.0643 (13)
H3A0.12820.40050.27230.097*
O40.21854 (13)0.3436 (4)0.3307 (2)0.0555 (12)
N40.15959 (17)0.4691 (5)0.2196 (3)0.0499 (14)
N50.19915 (17)0.4732 (5)0.2255 (3)0.0520 (14)
N60.39439 (18)0.5341 (5)0.3585 (3)0.0650 (16)
C170.0911 (2)0.5253 (6)0.1589 (4)0.0453 (16)
C180.0787 (2)0.4598 (6)0.2135 (4)0.0508 (17)
C190.0387 (3)0.4636 (7)0.2065 (5)0.072 (2)
H190.03060.41750.24140.086*
C200.0101 (2)0.5342 (8)0.1489 (5)0.075 (2)
H200.01680.53700.14560.090*
C210.0222 (2)0.6009 (7)0.0961 (4)0.0591 (19)
C220.0617 (2)0.5949 (6)0.1007 (4)0.0533 (18)
H220.06910.63840.06410.064*
C230.1324 (2)0.5246 (6)0.1638 (4)0.0492 (17)
H230.13940.56530.12570.059*
C240.2283 (2)0.4141 (6)0.2863 (4)0.0445 (16)
C250.27063 (18)0.4424 (5)0.2981 (3)0.0389 (15)
C260.3015 (2)0.3623 (6)0.3429 (3)0.0506 (17)
H260.29440.28590.36040.061*
C270.3415 (2)0.3897 (6)0.3625 (4)0.0552 (18)
H270.36080.33240.39330.066*
C280.3544 (2)0.5040 (6)0.3371 (4)0.0466 (16)
C290.3231 (2)0.5837 (6)0.2899 (4)0.0532 (18)
H290.32990.65900.27070.064*
C300.2829 (2)0.5538 (6)0.2713 (3)0.0494 (17)
H300.26330.60940.23980.059*
C310.4259 (2)0.4599 (8)0.4144 (5)0.104 (3)
H31A0.41930.44640.45970.155*
H31B0.45130.50500.42880.155*
H31C0.42830.37880.39210.155*
C320.4071 (2)0.6560 (6)0.3366 (4)0.069 (2)
H32A0.39080.67510.28360.103*
H32B0.43510.65080.34200.103*
H32C0.40390.72240.36970.103*
H20.2137 (19)0.345 (6)0.437 (3)0.080*
H50.2045 (19)0.509 (6)0.186 (3)0.080*
H10.1197 (5)0.314 (7)0.471 (4)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0913 (7)0.0587 (6)0.1314 (9)0.0037 (5)0.0073 (6)0.0273 (5)
O10.075 (4)0.097 (4)0.096 (4)0.017 (4)0.043 (4)0.043 (4)
O20.077 (3)0.058 (3)0.047 (3)0.006 (2)0.034 (3)0.007 (2)
N10.061 (4)0.041 (3)0.044 (3)0.002 (3)0.021 (3)0.002 (3)
N20.062 (4)0.049 (3)0.040 (3)0.005 (3)0.024 (3)0.005 (3)
N30.069 (4)0.059 (4)0.068 (4)0.013 (3)0.029 (4)0.004 (3)
C10.053 (5)0.045 (4)0.037 (4)0.000 (4)0.014 (3)0.007 (3)
C20.066 (5)0.065 (5)0.056 (5)0.008 (5)0.025 (4)0.008 (4)
C30.070 (6)0.103 (7)0.074 (6)0.010 (5)0.033 (5)0.011 (5)
C40.061 (5)0.090 (7)0.073 (6)0.016 (5)0.011 (5)0.004 (5)
C50.077 (6)0.047 (5)0.058 (5)0.011 (4)0.001 (4)0.004 (4)
C60.067 (5)0.052 (5)0.051 (4)0.001 (4)0.010 (4)0.001 (4)
C70.056 (5)0.047 (4)0.043 (4)0.011 (4)0.019 (3)0.008 (4)
C80.060 (4)0.044 (4)0.033 (4)0.009 (4)0.015 (3)0.001 (3)
C90.052 (4)0.037 (4)0.040 (4)0.005 (3)0.020 (3)0.000 (3)
C100.059 (4)0.042 (4)0.046 (4)0.001 (4)0.025 (4)0.007 (3)
C110.061 (5)0.057 (5)0.045 (4)0.003 (4)0.031 (4)0.011 (4)
C120.054 (4)0.037 (4)0.049 (4)0.001 (4)0.017 (4)0.001 (3)
C130.075 (5)0.043 (4)0.048 (4)0.009 (4)0.017 (4)0.015 (3)
C140.075 (5)0.045 (4)0.051 (4)0.001 (4)0.033 (4)0.004 (4)
C150.079 (6)0.092 (6)0.102 (6)0.037 (5)0.044 (5)0.015 (5)
C160.102 (6)0.043 (4)0.082 (6)0.016 (4)0.012 (5)0.010 (4)
Br20.0675 (6)0.0902 (7)0.1043 (7)0.0140 (5)0.0188 (5)0.0122 (5)
O30.083 (4)0.052 (3)0.064 (3)0.001 (3)0.034 (3)0.003 (3)
O40.072 (3)0.050 (3)0.044 (3)0.016 (2)0.021 (2)0.000 (2)
N40.050 (4)0.047 (3)0.056 (4)0.005 (3)0.023 (3)0.003 (3)
N50.060 (4)0.052 (4)0.045 (4)0.003 (3)0.020 (3)0.012 (3)
N60.058 (4)0.054 (4)0.080 (4)0.002 (3)0.022 (3)0.016 (3)
C170.053 (4)0.034 (4)0.048 (4)0.005 (3)0.018 (4)0.004 (3)
C180.064 (5)0.039 (4)0.058 (5)0.009 (4)0.032 (4)0.010 (4)
C190.080 (6)0.071 (5)0.080 (6)0.000 (5)0.046 (5)0.007 (5)
C200.060 (5)0.084 (6)0.091 (6)0.001 (5)0.039 (5)0.001 (5)
C210.052 (5)0.059 (5)0.065 (5)0.004 (4)0.021 (4)0.007 (4)
C220.065 (5)0.041 (4)0.060 (5)0.011 (4)0.030 (4)0.008 (4)
C230.051 (4)0.050 (4)0.045 (4)0.000 (4)0.015 (4)0.001 (3)
C240.062 (5)0.039 (4)0.033 (4)0.004 (4)0.018 (4)0.005 (3)
C250.052 (4)0.036 (4)0.032 (4)0.000 (3)0.019 (3)0.006 (3)
C260.075 (5)0.026 (4)0.051 (4)0.002 (4)0.023 (4)0.001 (3)
C270.057 (5)0.043 (4)0.060 (5)0.007 (4)0.016 (4)0.005 (4)
C280.059 (5)0.033 (4)0.050 (4)0.001 (4)0.022 (4)0.000 (3)
C290.073 (5)0.036 (4)0.053 (4)0.002 (4)0.025 (4)0.007 (3)
C300.064 (5)0.039 (4)0.043 (4)0.002 (3)0.017 (3)0.012 (3)
C310.069 (6)0.081 (6)0.135 (8)0.005 (5)0.007 (5)0.029 (6)
C320.080 (5)0.059 (5)0.068 (5)0.017 (4)0.029 (4)0.007 (4)
Geometric parameters (Å, º) top
Br1—C51.915 (7)Br2—C211.893 (7)
O1—C21.372 (8)O3—C181.352 (7)
O1—H10.852 (10)O3—H3A0.8200
O2—C81.232 (7)O4—C241.244 (7)
N1—C71.290 (7)N4—C231.266 (7)
N1—N21.390 (7)N4—N51.364 (7)
N2—C81.369 (7)N5—C241.364 (7)
N2—H20.900 (10)N5—H50.900 (10)
N3—C121.363 (7)N6—C281.358 (7)
N3—C151.432 (8)N6—C311.440 (8)
N3—C161.456 (8)N6—C321.457 (8)
C1—C21.375 (9)C17—C221.396 (8)
C1—C61.403 (8)C17—C181.417 (8)
C1—C71.460 (8)C17—C231.432 (8)
C2—C31.375 (9)C18—C191.373 (9)
C3—C41.356 (10)C19—C201.385 (9)
C3—H30.9300C19—H190.9300
C4—C51.370 (10)C20—C211.391 (9)
C4—H40.9300C20—H200.9300
C5—C61.374 (9)C21—C221.368 (8)
C6—H60.9300C22—H220.9300
C7—H70.9300C23—H230.9300
C8—C91.487 (8)C24—C251.462 (8)
C9—C101.373 (8)C25—C261.384 (8)
C9—C141.391 (8)C25—C301.396 (8)
C10—C111.374 (8)C26—C271.356 (8)
C10—H100.9300C26—H260.9300
C11—C121.418 (8)C27—C281.420 (8)
C11—H110.9300C27—H270.9300
C12—C131.387 (9)C28—C291.406 (8)
C13—C141.377 (8)C29—C301.371 (8)
C13—H130.9300C29—H290.9300
C14—H140.9300C30—H300.9300
C15—H15A0.9600C31—H31A0.9600
C15—H15B0.9600C31—H31B0.9600
C15—H15C0.9600C31—H31C0.9600
C16—H16A0.9600C32—H32A0.9600
C16—H16B0.9600C32—H32B0.9600
C16—H16C0.9600C32—H32C0.9600
C2—O1—H1104 (5)C18—O3—H3A109.5
C7—N1—N2117.9 (5)C23—N4—N5120.0 (5)
C8—N2—N1116.9 (5)N4—N5—C24119.7 (5)
C8—N2—H2125 (5)N4—N5—H5118 (4)
N1—N2—H2114 (4)C24—N5—H5122 (4)
C12—N3—C15121.0 (6)C28—N6—C31122.3 (6)
C12—N3—C16121.1 (6)C28—N6—C32121.1 (6)
C15—N3—C16117.8 (6)C31—N6—C32115.7 (6)
C2—C1—C6118.9 (6)C22—C17—C18117.7 (6)
C2—C1—C7122.8 (6)C22—C17—C23120.4 (6)
C6—C1—C7118.3 (6)C18—C17—C23121.9 (6)
O1—C2—C1121.5 (7)O3—C18—C19118.4 (7)
O1—C2—C3117.1 (7)O3—C18—C17121.8 (6)
C1—C2—C3121.4 (7)C19—C18—C17119.7 (7)
C4—C3—C2119.5 (8)C18—C19—C20121.7 (7)
C4—C3—H3120.2C18—C19—H19119.1
C2—C3—H3120.2C20—C19—H19119.1
C3—C4—C5120.1 (7)C19—C20—C21118.7 (7)
C3—C4—H4119.9C19—C20—H20120.6
C5—C4—H4119.9C21—C20—H20120.6
C4—C5—C6121.6 (7)C22—C21—C20120.3 (7)
C4—C5—Br1119.9 (6)C22—C21—Br2120.9 (6)
C6—C5—Br1118.5 (7)C20—C21—Br2118.7 (6)
C5—C6—C1118.4 (7)C21—C22—C17121.8 (6)
C5—C6—H6120.8C21—C22—H22119.1
C1—C6—H6120.8C17—C22—H22119.1
N1—C7—C1118.4 (6)N4—C23—C17120.4 (6)
N1—C7—H7120.8N4—C23—H23119.8
C1—C7—H7120.8C17—C23—H23119.8
O2—C8—N2119.7 (6)O4—C24—N5120.2 (6)
O2—C8—C9123.7 (6)O4—C24—C25122.6 (6)
N2—C8—C9116.6 (6)N5—C24—C25117.1 (6)
C10—C9—C14117.6 (6)C26—C25—C30115.9 (6)
C10—C9—C8124.3 (6)C26—C25—C24120.5 (6)
C14—C9—C8118.0 (6)C30—C25—C24123.4 (6)
C9—C10—C11122.4 (6)C27—C26—C25123.4 (6)
C9—C10—H10118.8C27—C26—H26118.3
C11—C10—H10118.8C25—C26—H26118.3
C10—C11—C12120.5 (6)C26—C27—C28121.4 (6)
C10—C11—H11119.7C26—C27—H27119.3
C12—C11—H11119.7C28—C27—H27119.3
N3—C12—C13122.2 (6)N6—C28—C29122.8 (6)
N3—C12—C11121.5 (6)N6—C28—C27121.8 (6)
C13—C12—C11116.3 (6)C29—C28—C27115.3 (6)
C14—C13—C12122.3 (6)C30—C29—C28122.0 (6)
C14—C13—H13118.9C30—C29—H29119.0
C12—C13—H13118.9C28—C29—H29119.0
C13—C14—C9120.8 (6)C29—C30—C25122.1 (6)
C13—C14—H14119.6C29—C30—H30119.0
C9—C14—H14119.6C25—C30—H30119.0
N3—C15—H15A109.5N6—C31—H31A109.5
N3—C15—H15B109.5N6—C31—H31B109.5
H15A—C15—H15B109.5H31A—C31—H31B109.5
N3—C15—H15C109.5N6—C31—H31C109.5
H15A—C15—H15C109.5H31A—C31—H31C109.5
H15B—C15—H15C109.5H31B—C31—H31C109.5
N3—C16—H16A109.5N6—C32—H32A109.5
N3—C16—H16B109.5N6—C32—H32B109.5
H16A—C16—H16B109.5H32A—C32—H32B109.5
N3—C16—H16C109.5N6—C32—H32C109.5
H16A—C16—H16C109.5H32A—C32—H32C109.5
H16B—C16—H16C109.5H32B—C32—H32C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.85 (1)1.78 (3)2.570 (7)153 (7)
O3—H3A···N40.821.872.588 (7)146
N2—H2···O40.90 (1)2.04 (2)2.920 (6)166 (6)
N5—H5···O2i0.90 (1)1.95 (3)2.807 (7)160 (6)
Symmetry code: (i) x, y+1, z1/2.

Experimental details

Crystal data
Chemical formulaC16H16BrN3O2
Mr362.23
Crystal system, space groupMonoclinic, C2/c
Temperature (K)298
a, b, c (Å)35.3800 (12), 10.452 (1), 18.5070 (15)
β (°) 111.463 (2)
V3)6369.1 (8)
Z16
Radiation typeMo Kα
µ (mm1)2.59
Crystal size (mm)0.20 × 0.20 × 0.18
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.625, 0.653
No. of measured, independent and
observed [I > 2σ(I)] reflections
25287, 6931, 2320
Rint0.168
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.065, 0.197, 0.94
No. of reflections6931
No. of parameters411
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.70, 0.44

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···AD—HH···AD···AD—H···A
O1—H1···N10.852 (10)1.78 (3)2.570 (7)153 (7)
O3—H3A···N40.821.872.588 (7)146
N2—H2···O40.90 (1)2.04 (2)2.920 (6)166 (6)
N5—H5···O2i0.90 (1)1.95 (3)2.807 (7)160 (6)
Symmetry code: (i) x, y+1, z1/2.
 

Acknowledgements

The author is grateful to the Zibo Vocational Institute for supporting this work.

References

First citationBruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationHorkaew, J., Chantrapromma, S., Anantapong, T., Kanjana-Opas, A. & Fun, H.-K. (2012). Acta Cryst. E68, o1069–o1070.  CSD CrossRef IUCr Journals
First citationLi, X.-Y. (2011a). Acta Cryst. E67, o1798.  Web of Science CSD CrossRef IUCr Journals
First citationLi, X.-Y. (2011b). Acta Cryst. E67, o2511.  Web of Science CSD CrossRef IUCr Journals
First citationLi, X.-Y. (2012). Acta Cryst. E68, o696.  CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWang, D.-Y., Meng, X.-F. & Ma, J.-J. (2012). Acta Cryst. E68, o21.  Web of Science CSD CrossRef IUCr Journals

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Volume 68| Part 5| May 2012| Page o1304
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