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ISSN: 2056-9890

4-Bromo-N-[4-(di­ethyl­amino)­benzyl­­idene]aniline

aCollege of Automation & Electronic Engineering, Qingdao University of Science & Technology, Qingdao 261500, People's Republic of China
*Correspondence e-mail: lixiaofangqd@163.com

(Received 8 August 2010; accepted 20 August 2010; online 28 August 2010)

The asymmetric unit of the title compound, C17H19BrN2, contains two independent mol­ecules. The dihedral angles between the two benzene rings in are 60.4 (2) and 61.0 (2)°.

Related literature

For applications of Schiff base compounds, see: Yu et al. (2007[Yu, Y. Y., Zhao, G. L. & Wen, Y. H. (2007). Chin. J. Struct. Chem. 26, 1359-1362.]). For related structures, see: You et al. (2004[You, X.-L., Lu, C.-R., Zhang, Y. & Zhang, D.-C. (2004). Acta Cryst. C60, o693-o695.]); Yu et al. (2007[Yu, Y. Y., Zhao, G. L. & Wen, Y. H. (2007). Chin. J. Struct. Chem. 26, 1359-1362.]); Zhang (2010[Zhang, F.-G. (2010). Acta Cryst. E66, o382.]).

[Scheme 1]

Experimental

Crystal data
  • C17H19BrN2

  • Mr = 331.25

  • Triclinic, [P \overline 1]

  • a = 10.1863 (11) Å

  • b = 12.3527 (13) Å

  • c = 14.3400 (15) Å

  • α = 112.936 (2)°

  • β = 92.986 (1)°

  • γ = 104.305 (1)°

  • V = 1587.8 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.58 mm−1

  • T = 298 K

  • 0.45 × 0.39 × 0.38 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.390, Tmax = 0.440

  • 8347 measured reflections

  • 5530 independent reflections

  • 2795 reflections with I > 2σ(I)

  • Rint = 0.031

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.115

  • S = 1.02

  • 5530 reflections

  • 365 parameters

  • H-atom parameters constrained

  • Δρmax = 0.45 e Å−3

  • Δρmin = −0.55 e Å−3

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). 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

Schiff base compounds have been used as fine chemicals and medical substrates. They are important ligands in coordination chemistry due to their ease of preparation (Yu et al., 2007). In this paper, the crystal structure of the title compound is reported. The asymmetric unit of the title compound contains two independent molecules (Fig. 1). The dihedral angles between the two benzene rings in each molecule are 60.4 (2) ° and 61.0 (2) °. Bond lengths and angles are comparable to those observed for 4-chloro-N-[4-(dimethylamino)benzylidene]aniline (You, et al., 2004) and 4-Chloro-N-[4-(diethylamino)benzylidene]aniline (Zhang, 2010).

Related literature top

For applications of Schiff base compounds, see: Yu et al. (2007). For related structures, see: You et al. (2004); Yu et al. (2007); Zhang (2010).

Experimental top

A mixture of 4-(diethylamino)benzaldehyde (0.01 mol) and 4-bromobenzenamine (0.01 mol) in ethanol (10 ml) was refluxed for 2 h. After cooling, filtration and drying, the title compound was obtained. 10 mg of the title compound was dissolved in 15 ml ethanol, and the solution was kept at room temperature. The single-crystal suitable for X-ray determination was obtained by evaporation from ethanol solution of the title compound after a week.

Refinement top

H atoms were initially located from difference maps and then refined in a riding model with C—H = 0.93–0.97 Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Structure description top

Schiff base compounds have been used as fine chemicals and medical substrates. They are important ligands in coordination chemistry due to their ease of preparation (Yu et al., 2007). In this paper, the crystal structure of the title compound is reported. The asymmetric unit of the title compound contains two independent molecules (Fig. 1). The dihedral angles between the two benzene rings in each molecule are 60.4 (2) ° and 61.0 (2) °. Bond lengths and angles are comparable to those observed for 4-chloro-N-[4-(dimethylamino)benzylidene]aniline (You, et al., 2004) and 4-Chloro-N-[4-(diethylamino)benzylidene]aniline (Zhang, 2010).

For applications of Schiff base compounds, see: Yu et al. (2007). For related structures, see: You et al. (2004); Yu et al. (2007); Zhang (2010).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 asymmetric unit of the title compound, drawn with 30% probability ellipsoids.
4-Bromo-N-[4-(diethylamino)benzylidene]aniline top
Crystal data top
C17H19BrN2Z = 4
Mr = 331.25F(000) = 680
Triclinic, P1Dx = 1.386 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.1863 (11) ÅCell parameters from 2343 reflections
b = 12.3527 (13) Åθ = 2.6–22.3°
c = 14.3400 (15) ŵ = 2.58 mm1
α = 112.936 (2)°T = 298 K
β = 92.986 (1)°Block, light yellow
γ = 104.305 (1)°0.45 × 0.39 × 0.38 mm
V = 1587.8 (3) Å3
Data collection top
Bruker SMART CCD
diffractometer
5530 independent reflections
Radiation source: fine-focus sealed tube2795 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
Detector resolution: 9 pixels mm-1θmax = 25.0°, θmin = 1.6°
φ and ω scansh = 1112
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1414
Tmin = 0.390, Tmax = 0.440l = 1713
8347 measured reflections
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.046P)2]
where P = (Fo2 + 2Fc2)/3
5530 reflections(Δ/σ)max = 0.001
365 parametersΔρmax = 0.45 e Å3
0 restraintsΔρmin = 0.55 e Å3
Crystal data top
C17H19BrN2γ = 104.305 (1)°
Mr = 331.25V = 1587.8 (3) Å3
Triclinic, P1Z = 4
a = 10.1863 (11) ÅMo Kα radiation
b = 12.3527 (13) ŵ = 2.58 mm1
c = 14.3400 (15) ÅT = 298 K
α = 112.936 (2)°0.45 × 0.39 × 0.38 mm
β = 92.986 (1)°
Data collection top
Bruker SMART CCD
diffractometer
5530 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2795 reflections with I > 2σ(I)
Tmin = 0.390, Tmax = 0.440Rint = 0.031
8347 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.115H-atom parameters constrained
S = 1.02Δρmax = 0.45 e Å3
5530 reflectionsΔρmin = 0.55 e Å3
365 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
Br10.63511 (6)0.55016 (5)0.91153 (4)0.0924 (2)
Br20.66046 (6)0.09334 (5)0.95086 (4)0.0763 (2)
N10.3683 (4)0.6583 (3)0.5818 (3)0.0545 (10)
N20.0254 (4)0.6568 (3)0.2131 (3)0.0618 (10)
N30.3916 (4)0.1413 (3)0.5863 (3)0.0548 (10)
N40.0089 (4)0.2236 (3)0.2607 (3)0.0546 (10)
C10.2611 (5)0.5804 (4)0.5184 (3)0.0527 (12)
H10.22600.50620.52350.063*
C20.1917 (5)0.6014 (4)0.4395 (3)0.0473 (11)
C30.0608 (5)0.5270 (4)0.3888 (3)0.0519 (11)
H30.02040.46220.40550.062*
C40.0118 (4)0.5440 (4)0.3156 (3)0.0521 (11)
H40.10010.49240.28490.062*
C50.0457 (5)0.6385 (4)0.2864 (3)0.0497 (11)
C60.1787 (5)0.7138 (4)0.3369 (3)0.0568 (12)
H60.22060.77710.31890.068*
C70.2474 (5)0.6970 (4)0.4109 (3)0.0570 (12)
H70.33420.75050.44370.068*
C80.1677 (5)0.5849 (4)0.1678 (3)0.0656 (14)
H8A0.21210.63190.14300.079*
H8B0.21560.57050.22050.079*
C90.1800 (6)0.4626 (5)0.0798 (4)0.0963 (18)
H9A0.13910.47630.02510.144*
H9B0.27530.41710.05540.144*
H9C0.13350.41670.10330.144*
C100.0409 (5)0.7398 (4)0.1669 (3)0.0661 (13)
H10A0.00010.70540.09510.079*
H10B0.13760.74480.17020.079*
C110.0271 (6)0.8664 (4)0.2190 (4)0.0936 (18)
H11A0.06830.86190.21980.140*
H11B0.06500.91430.18250.140*
H11C0.07570.90450.28830.140*
C120.4256 (4)0.6269 (4)0.6563 (3)0.0465 (11)
C130.4527 (4)0.5157 (4)0.6331 (3)0.0558 (12)
H130.42830.45580.56590.067*
C140.5154 (5)0.4918 (4)0.7080 (3)0.0608 (13)
H140.53390.41700.69150.073*
C150.5501 (4)0.5810 (4)0.8077 (3)0.0557 (12)
C160.5253 (4)0.6932 (4)0.8328 (3)0.0565 (12)
H160.54840.75210.90030.068*
C170.4664 (4)0.7169 (4)0.7578 (3)0.0533 (12)
H170.45330.79360.77410.064*
C180.2677 (5)0.1487 (4)0.5796 (3)0.0580 (12)
H180.21700.14000.62960.070*
C190.2032 (5)0.1699 (4)0.4987 (3)0.0500 (11)
C200.0633 (5)0.1592 (4)0.4867 (3)0.0579 (12)
H200.01220.13990.53290.070*
C210.0015 (5)0.1758 (4)0.4104 (3)0.0572 (12)
H210.09520.16750.40550.069*
C220.0708 (4)0.2051 (4)0.3388 (3)0.0484 (11)
C230.2142 (4)0.2194 (4)0.3527 (3)0.0501 (11)
H230.26700.24130.30830.060*
C240.2755 (4)0.2016 (4)0.4297 (3)0.0508 (11)
H240.36940.21110.43630.061*
C250.1419 (4)0.1959 (4)0.2406 (3)0.0645 (13)
H25A0.16520.23600.19860.077*
H25B0.17380.23030.30540.077*
C260.2177 (5)0.0589 (4)0.1868 (4)0.0831 (16)
H26A0.18750.02410.12220.125*
H26B0.31470.04770.17520.125*
H26C0.19840.01890.22910.125*
C270.0858 (5)0.2632 (4)0.1898 (3)0.0614 (13)
H27A0.17680.31580.22630.074*
H27B0.03960.31150.16830.074*
C280.1001 (6)0.1581 (5)0.0958 (4)0.0974 (18)
H28A0.13780.10530.11630.146*
H28B0.16020.18990.05710.146*
H28C0.01150.11230.05400.146*
C290.4486 (4)0.1290 (4)0.6724 (3)0.0477 (11)
C300.5184 (4)0.0424 (4)0.6583 (3)0.0576 (12)
H300.52360.00930.59190.069*
C310.5808 (4)0.0306 (4)0.7406 (3)0.0550 (12)
H310.62470.02980.72990.066*
C320.5762 (4)0.1106 (4)0.8388 (3)0.0515 (11)
C330.5105 (5)0.1977 (4)0.8546 (3)0.0561 (12)
H330.50860.25110.92120.067*
C340.4466 (5)0.2079 (4)0.7729 (3)0.0565 (12)
H340.40160.26780.78460.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.1166 (6)0.0896 (5)0.0824 (4)0.0230 (4)0.0006 (3)0.0539 (3)
Br20.0902 (4)0.0839 (4)0.0634 (3)0.0281 (3)0.0118 (3)0.0378 (3)
N10.053 (3)0.051 (2)0.058 (2)0.008 (2)0.009 (2)0.024 (2)
N20.058 (3)0.057 (3)0.070 (3)0.004 (2)0.001 (2)0.035 (2)
N30.059 (3)0.056 (2)0.050 (2)0.017 (2)0.014 (2)0.0225 (19)
N40.048 (3)0.053 (2)0.065 (2)0.016 (2)0.014 (2)0.026 (2)
C10.056 (3)0.042 (3)0.057 (3)0.013 (3)0.018 (2)0.016 (2)
C20.050 (3)0.045 (3)0.048 (3)0.015 (3)0.012 (2)0.020 (2)
C30.059 (3)0.039 (3)0.054 (3)0.007 (3)0.014 (2)0.020 (2)
C40.050 (3)0.043 (3)0.055 (3)0.001 (2)0.003 (2)0.020 (2)
C50.055 (3)0.044 (3)0.051 (3)0.015 (3)0.011 (2)0.020 (2)
C60.052 (3)0.045 (3)0.073 (3)0.002 (3)0.013 (3)0.032 (3)
C70.046 (3)0.058 (3)0.065 (3)0.009 (3)0.008 (2)0.028 (3)
C80.062 (4)0.066 (4)0.076 (3)0.020 (3)0.006 (3)0.037 (3)
C90.111 (5)0.076 (4)0.090 (4)0.023 (4)0.017 (3)0.029 (3)
C100.070 (4)0.069 (4)0.067 (3)0.023 (3)0.011 (3)0.033 (3)
C110.108 (5)0.078 (4)0.115 (4)0.040 (4)0.038 (4)0.050 (4)
C120.042 (3)0.046 (3)0.053 (3)0.010 (2)0.014 (2)0.023 (2)
C130.069 (3)0.048 (3)0.049 (3)0.015 (3)0.015 (2)0.019 (2)
C140.078 (4)0.048 (3)0.065 (3)0.025 (3)0.027 (3)0.027 (3)
C150.058 (3)0.061 (3)0.063 (3)0.019 (3)0.021 (2)0.038 (3)
C160.056 (3)0.058 (3)0.051 (3)0.015 (3)0.013 (2)0.019 (2)
C170.052 (3)0.048 (3)0.061 (3)0.018 (2)0.018 (2)0.021 (3)
C180.062 (3)0.053 (3)0.049 (3)0.009 (3)0.016 (3)0.016 (2)
C190.055 (3)0.048 (3)0.043 (3)0.014 (2)0.014 (2)0.015 (2)
C200.052 (3)0.065 (3)0.061 (3)0.020 (3)0.029 (2)0.027 (3)
C210.047 (3)0.065 (3)0.065 (3)0.020 (3)0.024 (3)0.029 (3)
C220.045 (3)0.037 (3)0.055 (3)0.012 (2)0.009 (2)0.011 (2)
C230.043 (3)0.051 (3)0.052 (3)0.010 (2)0.015 (2)0.019 (2)
C240.043 (3)0.048 (3)0.055 (3)0.015 (2)0.010 (2)0.013 (2)
C250.046 (3)0.065 (4)0.087 (3)0.019 (3)0.010 (3)0.034 (3)
C260.054 (3)0.066 (4)0.120 (4)0.010 (3)0.004 (3)0.036 (3)
C270.067 (3)0.061 (3)0.060 (3)0.021 (3)0.009 (3)0.028 (3)
C280.098 (5)0.089 (4)0.079 (4)0.015 (4)0.029 (3)0.013 (3)
C290.045 (3)0.042 (3)0.054 (3)0.007 (2)0.017 (2)0.020 (2)
C300.068 (3)0.057 (3)0.048 (3)0.022 (3)0.023 (2)0.018 (2)
C310.060 (3)0.050 (3)0.062 (3)0.021 (3)0.024 (2)0.026 (3)
C320.058 (3)0.044 (3)0.050 (3)0.009 (2)0.010 (2)0.020 (2)
C330.069 (3)0.044 (3)0.049 (3)0.014 (3)0.023 (2)0.013 (2)
C340.068 (3)0.047 (3)0.057 (3)0.025 (3)0.023 (2)0.018 (3)
Geometric parameters (Å, º) top
Br1—C151.893 (4)C14—C151.382 (6)
Br2—C321.891 (4)C14—H140.9300
N1—C11.281 (5)C15—C161.381 (6)
N1—C121.414 (5)C16—C171.367 (5)
N2—C51.367 (5)C16—H160.9300
N2—C81.459 (5)C17—H170.9300
N2—C101.476 (5)C18—C191.444 (5)
N3—C181.290 (5)C18—H180.9300
N3—C291.414 (5)C19—C241.382 (5)
N4—C221.378 (5)C19—C201.394 (5)
N4—C271.472 (5)C20—C211.356 (5)
N4—C251.476 (5)C20—H200.9300
C1—C21.443 (5)C21—C221.402 (5)
C1—H10.9300C21—H210.9300
C2—C31.387 (5)C22—C231.422 (5)
C2—C71.399 (6)C23—C241.358 (5)
C3—C41.363 (5)C23—H230.9300
C3—H30.9300C24—H240.9300
C4—C51.397 (5)C25—C261.526 (6)
C4—H40.9300C25—H25A0.9700
C5—C61.405 (6)C25—H25B0.9700
C6—C71.350 (5)C26—H26A0.9600
C6—H60.9300C26—H26B0.9600
C7—H70.9300C26—H26C0.9600
C8—C91.515 (6)C27—C281.508 (6)
C8—H8A0.9700C27—H27A0.9700
C8—H8B0.9700C27—H27B0.9700
C9—H9A0.9600C28—H28A0.9600
C9—H9B0.9600C28—H28B0.9600
C9—H9C0.9600C28—H28C0.9600
C10—C111.494 (6)C29—C301.384 (5)
C10—H10A0.9700C29—C341.394 (5)
C10—H10B0.9700C30—C311.384 (5)
C11—H11A0.9600C30—H300.9300
C11—H11B0.9600C31—C321.381 (5)
C11—H11C0.9600C31—H310.9300
C12—C131.384 (5)C32—C331.357 (5)
C12—C171.405 (5)C33—C341.374 (5)
C13—C141.385 (5)C33—H330.9300
C13—H130.9300C34—H340.9300
C1—N1—C12118.0 (4)C15—C16—H16120.2
C5—N2—C8121.6 (4)C16—C17—C12120.9 (4)
C5—N2—C10122.2 (4)C16—C17—H17119.5
C8—N2—C10115.9 (3)C12—C17—H17119.5
C18—N3—C29119.3 (4)N3—C18—C19123.7 (4)
C22—N4—C27123.0 (4)N3—C18—H18118.2
C22—N4—C25120.2 (4)C19—C18—H18118.2
C27—N4—C25116.7 (3)C24—C19—C20116.5 (4)
N1—C1—C2123.6 (4)C24—C19—C18122.4 (4)
N1—C1—H1118.2C20—C19—C18121.1 (4)
C2—C1—H1118.2C21—C20—C19122.8 (4)
C3—C2—C7115.8 (4)C21—C20—H20118.6
C3—C2—C1120.5 (4)C19—C20—H20118.6
C7—C2—C1123.7 (4)C20—C21—C22120.9 (4)
C4—C3—C2123.4 (4)C20—C21—H21119.6
C4—C3—H3118.3C22—C21—H21119.6
C2—C3—H3118.3N4—C22—C21122.6 (4)
C3—C4—C5120.3 (4)N4—C22—C23121.0 (4)
C3—C4—H4119.8C21—C22—C23116.4 (4)
C5—C4—H4119.8C24—C23—C22121.1 (4)
N2—C5—C4121.1 (4)C24—C23—H23119.5
N2—C5—C6122.2 (4)C22—C23—H23119.5
C4—C5—C6116.6 (4)C23—C24—C19122.3 (4)
C7—C6—C5122.0 (4)C23—C24—H24118.8
C7—C6—H6119.0C19—C24—H24118.8
C5—C6—H6119.0N4—C25—C26113.9 (3)
C6—C7—C2121.8 (4)N4—C25—H25A108.8
C6—C7—H7119.1C26—C25—H25A108.8
C2—C7—H7119.1N4—C25—H25B108.8
N2—C8—C9112.8 (4)C26—C25—H25B108.8
N2—C8—H8A109.0H25A—C25—H25B107.7
C9—C8—H8A109.0C25—C26—H26A109.5
N2—C8—H8B109.0C25—C26—H26B109.5
C9—C8—H8B109.0H26A—C26—H26B109.5
H8A—C8—H8B107.8C25—C26—H26C109.5
C8—C9—H9A109.5H26A—C26—H26C109.5
C8—C9—H9B109.5H26B—C26—H26C109.5
H9A—C9—H9B109.5N4—C27—C28113.6 (4)
C8—C9—H9C109.5N4—C27—H27A108.8
H9A—C9—H9C109.5C28—C27—H27A108.8
H9B—C9—H9C109.5N4—C27—H27B108.8
N2—C10—C11113.0 (4)C28—C27—H27B108.8
N2—C10—H10A109.0H27A—C27—H27B107.7
C11—C10—H10A109.0C27—C28—H28A109.5
N2—C10—H10B109.0C27—C28—H28B109.5
C11—C10—H10B109.0H28A—C28—H28B109.5
H10A—C10—H10B107.8C27—C28—H28C109.5
C10—C11—H11A109.5H28A—C28—H28C109.5
C10—C11—H11B109.5H28B—C28—H28C109.5
H11A—C11—H11B109.5C30—C29—C34117.8 (4)
C10—C11—H11C109.5C30—C29—N3119.7 (4)
H11A—C11—H11C109.5C34—C29—N3122.3 (4)
H11B—C11—H11C109.5C29—C30—C31121.7 (4)
C13—C12—C17118.3 (4)C29—C30—H30119.2
C13—C12—N1123.5 (4)C31—C30—H30119.2
C17—C12—N1118.1 (4)C32—C31—C30118.6 (4)
C12—C13—C14121.2 (4)C32—C31—H31120.7
C12—C13—H13119.4C30—C31—H31120.7
C14—C13—H13119.4C33—C32—C31120.8 (4)
C15—C14—C13118.9 (4)C33—C32—Br2120.8 (3)
C15—C14—H14120.5C31—C32—Br2118.3 (3)
C13—C14—H14120.5C32—C33—C34120.5 (4)
C16—C15—C14121.1 (4)C32—C33—H33119.7
C16—C15—Br1119.3 (3)C34—C33—H33119.7
C14—C15—Br1119.7 (3)C33—C34—C29120.5 (4)
C17—C16—C15119.5 (4)C33—C34—H34119.7
C17—C16—H16120.2C29—C34—H34119.7
C12—N1—C1—C2179.3 (4)C29—N3—C18—C19175.5 (4)
N1—C1—C2—C3165.6 (4)N3—C18—C19—C249.6 (7)
N1—C1—C2—C712.7 (7)N3—C18—C19—C20170.5 (4)
C7—C2—C3—C40.3 (6)C24—C19—C20—C211.5 (6)
C1—C2—C3—C4178.2 (4)C18—C19—C20—C21178.5 (4)
C2—C3—C4—C51.3 (6)C19—C20—C21—C220.1 (7)
C8—N2—C5—C44.7 (6)C27—N4—C22—C21175.4 (4)
C10—N2—C5—C4168.3 (4)C25—N4—C22—C218.7 (6)
C8—N2—C5—C6174.5 (4)C27—N4—C22—C232.3 (6)
C10—N2—C5—C612.5 (6)C25—N4—C22—C23173.6 (4)
C3—C4—C5—N2179.9 (4)C20—C21—C22—N4179.5 (4)
C3—C4—C5—C60.8 (6)C20—C21—C22—C231.6 (6)
N2—C5—C6—C7178.5 (4)N4—C22—C23—C24179.8 (4)
C4—C5—C6—C70.7 (6)C21—C22—C23—C241.9 (6)
C5—C6—C7—C21.8 (7)C22—C23—C24—C190.5 (6)
C3—C2—C7—C61.3 (6)C20—C19—C24—C231.2 (6)
C1—C2—C7—C6179.7 (4)C18—C19—C24—C23178.8 (4)
C5—N2—C8—C984.0 (5)C22—N4—C25—C2675.2 (5)
C10—N2—C8—C989.5 (5)C27—N4—C25—C26101.0 (5)
C5—N2—C10—C1194.6 (5)C22—N4—C27—C2889.2 (5)
C8—N2—C10—C1192.0 (5)C25—N4—C27—C2886.9 (5)
C1—N1—C12—C1348.8 (6)C18—N3—C29—C30133.9 (4)
C1—N1—C12—C17136.0 (4)C18—N3—C29—C3451.2 (6)
C17—C12—C13—C141.5 (7)C34—C29—C30—C312.1 (6)
N1—C12—C13—C14176.7 (4)N3—C29—C30—C31177.3 (4)
C12—C13—C14—C150.6 (7)C29—C30—C31—C322.1 (7)
C13—C14—C15—C161.1 (7)C30—C31—C32—C330.9 (7)
C13—C14—C15—Br1179.7 (3)C30—C31—C32—Br2179.6 (3)
C14—C15—C16—C170.5 (7)C31—C32—C33—C340.2 (7)
Br1—C15—C16—C17178.7 (3)Br2—C32—C33—C34178.4 (3)
C15—C16—C17—C122.7 (7)C32—C33—C34—C290.2 (7)
C13—C12—C17—C163.2 (6)C30—C29—C34—C330.9 (7)
N1—C12—C17—C16178.6 (4)N3—C29—C34—C33176.0 (4)

Experimental details

Crystal data
Chemical formulaC17H19BrN2
Mr331.25
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)10.1863 (11), 12.3527 (13), 14.3400 (15)
α, β, γ (°)112.936 (2), 92.986 (1), 104.305 (1)
V3)1587.8 (3)
Z4
Radiation typeMo Kα
µ (mm1)2.58
Crystal size (mm)0.45 × 0.39 × 0.38
Data collection
DiffractometerBruker SMART CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.390, 0.440
No. of measured, independent and
observed [I > 2σ(I)] reflections
8347, 5530, 2795
Rint0.031
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.115, 1.02
No. of reflections5530
No. of parameters365
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.45, 0.55

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

References

First citationBruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationYou, X.-L., Lu, C.-R., Zhang, Y. & Zhang, D.-C. (2004). Acta Cryst. C60, o693–o695.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationYu, Y. Y., Zhao, G. L. & Wen, Y. H. (2007). Chin. J. Struct. Chem. 26, 1359–1362.  Google Scholar
First citationZhang, F.-G. (2010). Acta Cryst. E66, o382.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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