organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

3-(4-Bromo­phen­yl)-1-phenyl-1H-pyrazole-4-carbaldehyde

aEberhard-Karls-University Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany, and bUniversity Mainz, Institut of Organic Chemistry, Duesbergweg 10-14, 55099 Mainz, Germany
*Correspondence e-mail: stefan.laufer@uni-tuebingen.de

(Received 12 November 2012; accepted 13 November 2012; online 24 November 2012)

The asymmetric unit of the title compound, C16H11BrN2O, contains two independent mol­ecules with slightly different geometries. The 4-bromo­benzene ring forms dihedral angles of 26.0 (2) and 39.9 (7)° with the pyrazole ring in the two mol­ecules while the phenyl ring is oriented at 19.7 (5) and 7.3 (0)° with respect to the pyrazole ring.

Related literature

For the biological activity of inhibitors for the microsomal prostaglandin E2 synthase-1 (mPGES-1) and 5-lipoxygenase (5-LO), see: Elkady et al. (2012[Elkady, M., Niess, R., Schaible, A. M., Bauer, J., Luderer, S., Ambrosi, G., Werz, O. & Laufer, S. A. (2012). J. Med. Chem. 55, 8958-8962.]). For details of the synthesis, see: Rathelot et al. (2002[Rathelot, P., Azas, N., El-Kashef, H., Delmas, F., Di Giorgio, C., Timon-David, P., Maldonado, J. & Vanelle, P. (2002). Eur. J. Med. Chem. 37, 671-679.]).

[Scheme 1]

Experimental

Crystal data
  • C16H11BrN2O

  • Mr = 327.18

  • Triclinic, [P \overline 1]

  • a = 9.6716 (8) Å

  • b = 11.4617 (9) Å

  • c = 13.8257 (10) Å

  • α = 113.497 (5)°

  • β = 92.753 (6)°

  • γ = 93.753 (6)°

  • V = 1397.91 (19) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.94 mm−1

  • T = 298 K

  • 0.34 × 0.18 × 0.06 mm

Data collection
  • Stoe IPDS 2T diffractometer

  • Absorption correction: multi-scan (MULABS; Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.477, Tmax = 0.660

  • 14312 measured reflections

  • 6740 independent reflections

  • 2856 reflections with I > 2σ(I)

  • Rint = 0.063

Refinement
  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 0.158

  • S = 0.92

  • 6740 reflections

  • 361 parameters

  • H-atom parameters constrained

  • Δρmax = 0.52 e Å−3

  • Δρmin = −0.73 e Å−3

Data collection: X-AREA (Stoe & Cie, 2010[Stoe & Cie (2010). X-AREA and X-RED. Stoe & Cie GmbH, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2010[Stoe & Cie (2010). X-AREA and X-RED. Stoe & Cie GmbH, Darmstadt, Germany.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.

Supporting information


Comment top

We synthesized and evaluated inhibitors for the microsomal prostaglandin E2 synthase-1 (mPGES-1) and 5-lipoxygenase (5-LO) (Elkady et al., 2012). The title compound was synthesized to obtain a template which leads to series of different derivates of the pyrazole scaffold (Rathelot et al., 2002) the asymmetric unit of the crystal structure contains two slightly different molecules.

The 4-Bromobenzene ring is oriented with dihedral angles of 26.0 (2)°, 39.9 (7)° (first and second molecule) with the pyrazole ring. The phenyl ring is oriented with dihedral angles of 19.7 (5)°, 7.3 (0)° with the pyrazole ring.

Related literature top

For the biological activity of inhibitors for the microsomal prostaglandin E2 synthase-1 (mPGES-1) and 5-lipoxygenase (5-LO), see: Elkady et al. (2012). For details of the synthesis, see: Rathelot et al. (2002).

Experimental top

The compound was prepared by a Vilsmeyer–Haack reaction. Phosphoryl chloride (4.16 ml, 44.7 mmol) was added dropwise to ice-cooled solution of 7 ml dimethylformamide. The mixture was left stirring for 30 min at 273 K. 4.3 g (14.9 mmol) of (E)-1-(1-(4-bromophenyl)ethylidene)-2-phenylhydrazine were dissolved in 10 ml dimethylformamide, and then slowly added to the mixture. The mixture was heated to 343 K and left for stirring for 4 h. The mixture was cooled to 273 K, quenched by water and adjusted to pH 12 with aqueous saturated sodium carbonate solution. The product was extracted with ethyl acetate three times, dried over anhydrous sodium sulfate and finally concentrated under vacuum. The product was purified by washing with methanol. Crystals of the title compound were obtained by slow evaporation of methanol at room temperature.

Refinement top

Hydrogen atoms were placed at calculated positions with C—H = 0.95 Å (aromatic) or 0.99–1.00 Å (sp3 C-atom). All H atoms were refined with isotropic displacement parameters (set at 1.2–1.5 times of the Ueq of the parent atom).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2010); cell refinement: X-AREA (Stoe & Cie, 2010); data reduction: X-RED (Stoe & Cie, 2010); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. View of compound I. Displacement ellipsoids are drawn at the 50% probability level.
3-(4-Bromophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde top
Crystal data top
C16H11BrN2OZ = 4
Mr = 327.18F(000) = 656
Triclinic, P1Dx = 1.555 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.6716 (8) ÅCell parameters from 5561 reflections
b = 11.4617 (9) Åθ = 2.7–28.0°
c = 13.8257 (10) ŵ = 2.94 mm1
α = 113.497 (5)°T = 298 K
β = 92.753 (6)°Block, colourless
γ = 93.753 (6)°0.34 × 0.18 × 0.06 mm
V = 1397.91 (19) Å3
Data collection top
Stoe IPDS 2T
diffractometer
6740 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus2856 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.063
Detector resolution: 6.67 pixels mm-1θmax = 28.0°, θmin = 2.6°
rotation method scansh = 1211
Absorption correction: multi-scan
(MULABS; Blessing, 1995)
k = 1515
Tmin = 0.477, Tmax = 0.660l = 1818
14312 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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158H-atom parameters constrained
S = 0.92 w = 1/[σ2(Fo2) + (0.0707P)2]
where P = (Fo2 + 2Fc2)/3
6740 reflections(Δ/σ)max < 0.001
361 parametersΔρmax = 0.52 e Å3
0 restraintsΔρmin = 0.73 e Å3
Crystal data top
C16H11BrN2Oγ = 93.753 (6)°
Mr = 327.18V = 1397.91 (19) Å3
Triclinic, P1Z = 4
a = 9.6716 (8) ÅMo Kα radiation
b = 11.4617 (9) ŵ = 2.94 mm1
c = 13.8257 (10) ÅT = 298 K
α = 113.497 (5)°0.34 × 0.18 × 0.06 mm
β = 92.753 (6)°
Data collection top
Stoe IPDS 2T
diffractometer
6740 independent reflections
Absorption correction: multi-scan
(MULABS; Blessing, 1995)
2856 reflections with I > 2σ(I)
Tmin = 0.477, Tmax = 0.660Rint = 0.063
14312 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.158H-atom parameters constrained
S = 0.92Δρmax = 0.52 e Å3
6740 reflectionsΔρmin = 0.73 e Å3
361 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
Br10.32448 (7)0.17418 (5)0.10411 (4)0.0974 (3)
N10.2200 (3)0.6242 (3)0.3849 (2)0.0482 (8)
N20.2418 (3)0.7380 (3)0.4705 (2)0.0456 (7)
C30.3427 (4)0.8149 (3)0.4591 (3)0.0468 (9)
H30.37430.89670.50780.056*
C40.3921 (4)0.7507 (3)0.3612 (3)0.0456 (9)
C50.3115 (4)0.6312 (3)0.3181 (3)0.0457 (9)
C60.1618 (4)0.7599 (3)0.5587 (3)0.0450 (9)
C70.1515 (4)0.8810 (4)0.6313 (3)0.0570 (10)
H70.19470.95070.62260.068*
C80.0763 (5)0.8990 (4)0.7178 (3)0.0660 (12)
H80.07100.98140.76830.079*
C90.0099 (5)0.7980 (4)0.7302 (4)0.0692 (12)
H90.04170.81100.78810.083*
C100.0202 (5)0.6772 (4)0.6565 (4)0.0703 (13)
H100.02560.60780.66410.084*
C110.0976 (4)0.6567 (4)0.5708 (3)0.0579 (11)
H110.10610.57410.52190.070*
C120.5114 (4)0.7921 (4)0.3201 (3)0.0537 (10)
H120.53840.73510.25590.064*
O130.5781 (3)0.8928 (3)0.3614 (2)0.0668 (8)
C140.3153 (4)0.5230 (4)0.2171 (3)0.0456 (9)
C150.3337 (4)0.5387 (4)0.1243 (3)0.0556 (10)
H150.34540.62090.12640.067*
C160.3352 (4)0.4363 (4)0.0292 (3)0.0626 (11)
H160.34600.44880.03260.075*
C170.3207 (4)0.3157 (4)0.0265 (3)0.0610 (11)
C180.3015 (4)0.2953 (4)0.1167 (3)0.0583 (11)
H180.29040.21280.11390.070*
C190.2991 (4)0.3994 (4)0.2112 (3)0.0524 (10)
H190.28630.38630.27250.063*
Br20.83318 (7)0.15393 (6)0.08996 (5)0.1091 (3)
N210.7249 (3)0.6207 (3)0.3891 (2)0.0473 (8)
N220.7455 (3)0.7353 (3)0.4734 (2)0.0453 (7)
C230.8472 (4)0.8114 (3)0.4605 (3)0.0487 (9)
H230.87950.89340.50840.058*
C240.8949 (4)0.7456 (3)0.3631 (3)0.0478 (9)
C250.8145 (4)0.6255 (3)0.3209 (3)0.0457 (9)
C260.6588 (4)0.7623 (4)0.5591 (3)0.0484 (9)
C270.6652 (5)0.8807 (4)0.6382 (3)0.0638 (12)
H270.72940.94510.63900.077*
C280.5759 (5)0.9050 (4)0.7174 (4)0.0692 (12)
H280.58130.98580.77210.083*
C290.4796 (5)0.8119 (4)0.7167 (3)0.0623 (11)
H290.41920.82880.77000.075*
C300.4738 (4)0.6930 (4)0.6357 (4)0.0620 (11)
H300.40840.62890.63420.074*
C310.5632 (4)0.6669 (4)0.5567 (3)0.0553 (10)
H310.55890.58580.50240.066*
C320.9995 (4)0.7970 (4)0.3158 (3)0.0593 (11)
H321.01240.75040.24490.071*
O331.0705 (3)0.8950 (3)0.3615 (3)0.0702 (9)
C340.8187 (4)0.5151 (3)0.2220 (3)0.0477 (9)
C350.9388 (4)0.4886 (4)0.1687 (3)0.0595 (11)
H351.01880.54430.19660.071*
C360.9428 (4)0.3834 (4)0.0769 (4)0.0657 (12)
H361.02390.36910.04200.079*
C370.8276 (5)0.2994 (4)0.0365 (3)0.0630 (11)
C380.7060 (5)0.3220 (4)0.0872 (3)0.0623 (11)
H380.62710.26470.05950.075*
C390.7026 (4)0.4291 (4)0.1782 (3)0.0543 (10)
H390.62020.44460.21140.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.1105 (5)0.0877 (4)0.0613 (3)0.0126 (3)0.0273 (3)0.0034 (3)
N10.0435 (19)0.0514 (17)0.0455 (17)0.0017 (14)0.0070 (14)0.0157 (15)
N20.0432 (19)0.0482 (17)0.0444 (17)0.0026 (14)0.0089 (14)0.0180 (15)
C30.045 (2)0.0484 (19)0.047 (2)0.0034 (17)0.0084 (17)0.0208 (18)
C40.040 (2)0.051 (2)0.046 (2)0.0008 (16)0.0083 (17)0.0208 (18)
C50.038 (2)0.055 (2)0.045 (2)0.0029 (17)0.0066 (17)0.0212 (18)
C60.041 (2)0.055 (2)0.041 (2)0.0006 (17)0.0086 (16)0.0219 (18)
C70.059 (3)0.054 (2)0.057 (2)0.0005 (19)0.015 (2)0.021 (2)
C80.065 (3)0.063 (3)0.058 (3)0.004 (2)0.018 (2)0.010 (2)
C90.068 (3)0.080 (3)0.054 (3)0.002 (2)0.023 (2)0.021 (2)
C100.076 (3)0.073 (3)0.066 (3)0.007 (2)0.024 (2)0.033 (3)
C110.062 (3)0.055 (2)0.054 (2)0.002 (2)0.015 (2)0.018 (2)
C120.053 (3)0.062 (2)0.052 (2)0.003 (2)0.0122 (19)0.028 (2)
O130.0653 (19)0.0557 (16)0.075 (2)0.0154 (14)0.0153 (16)0.0234 (15)
C140.034 (2)0.060 (2)0.043 (2)0.0019 (17)0.0079 (16)0.0206 (18)
C150.057 (3)0.059 (2)0.053 (2)0.0051 (19)0.0065 (19)0.026 (2)
C160.062 (3)0.077 (3)0.046 (2)0.011 (2)0.006 (2)0.024 (2)
C170.053 (3)0.068 (3)0.047 (2)0.006 (2)0.0162 (19)0.007 (2)
C180.055 (3)0.050 (2)0.064 (3)0.0037 (18)0.016 (2)0.016 (2)
C190.052 (2)0.056 (2)0.051 (2)0.0059 (18)0.0121 (18)0.0232 (19)
Br20.1057 (5)0.0904 (4)0.0834 (4)0.0047 (3)0.0324 (4)0.0156 (3)
N210.0460 (19)0.0457 (16)0.0471 (18)0.0029 (14)0.0079 (15)0.0162 (15)
N220.0445 (19)0.0414 (15)0.0457 (17)0.0028 (13)0.0053 (14)0.0138 (14)
C230.046 (2)0.0447 (19)0.052 (2)0.0031 (17)0.0096 (18)0.0164 (18)
C240.043 (2)0.049 (2)0.051 (2)0.0016 (17)0.0074 (18)0.0198 (18)
C250.040 (2)0.049 (2)0.046 (2)0.0013 (16)0.0015 (17)0.0177 (18)
C260.047 (2)0.052 (2)0.048 (2)0.0028 (17)0.0075 (18)0.0221 (19)
C270.063 (3)0.055 (2)0.061 (3)0.007 (2)0.012 (2)0.012 (2)
C280.069 (3)0.067 (3)0.059 (3)0.006 (2)0.017 (2)0.010 (2)
C290.056 (3)0.082 (3)0.055 (3)0.011 (2)0.017 (2)0.031 (2)
C300.058 (3)0.066 (3)0.066 (3)0.004 (2)0.013 (2)0.031 (2)
C310.056 (3)0.052 (2)0.055 (2)0.0034 (19)0.011 (2)0.0189 (19)
C320.064 (3)0.053 (2)0.062 (3)0.001 (2)0.020 (2)0.023 (2)
O330.0640 (19)0.0537 (16)0.088 (2)0.0133 (14)0.0199 (16)0.0247 (16)
C340.041 (2)0.055 (2)0.049 (2)0.0007 (17)0.0062 (17)0.0231 (19)
C350.040 (2)0.063 (2)0.062 (3)0.0044 (18)0.0065 (19)0.012 (2)
C360.043 (2)0.072 (3)0.070 (3)0.004 (2)0.020 (2)0.015 (2)
C370.066 (3)0.060 (2)0.052 (2)0.004 (2)0.018 (2)0.009 (2)
C380.053 (3)0.064 (2)0.057 (3)0.011 (2)0.006 (2)0.013 (2)
C390.043 (2)0.062 (2)0.052 (2)0.0064 (18)0.0100 (18)0.018 (2)
Geometric parameters (Å, º) top
Br1—C171.890 (4)Br2—C371.880 (4)
N1—C51.330 (4)N21—C251.326 (4)
N1—N21.363 (4)N21—N221.358 (4)
N2—C31.330 (4)N22—C231.337 (4)
N2—C61.421 (4)N22—C261.428 (5)
C3—C41.383 (5)C23—C241.375 (5)
C3—H30.9300C23—H230.9300
C4—C51.416 (5)C24—C251.420 (5)
C4—C121.445 (5)C24—C321.446 (5)
C5—C141.457 (5)C25—C341.451 (5)
C6—C71.364 (5)C26—C271.357 (6)
C6—C111.372 (5)C26—C311.374 (5)
C7—C81.382 (6)C27—C281.379 (6)
C7—H70.9300C27—H270.9300
C8—C91.362 (6)C28—C291.366 (6)
C8—H80.9300C28—H280.9300
C9—C101.367 (6)C29—C301.371 (6)
C9—H90.9300C29—H290.9300
C10—C111.381 (5)C30—C311.377 (5)
C10—H100.9300C30—H300.9300
C11—H110.9300C31—H310.9300
C12—O131.190 (4)C32—O331.193 (5)
C12—H120.9300C32—H320.9300
C14—C151.383 (5)C34—C391.383 (5)
C14—C191.384 (5)C34—C351.391 (5)
C15—C161.371 (6)C35—C361.363 (6)
C15—H150.9300C35—H350.9300
C16—C171.365 (6)C36—C371.361 (6)
C16—H160.9300C36—H360.9300
C17—C181.377 (6)C37—C381.384 (6)
C18—C191.376 (5)C38—C391.368 (5)
C18—H180.9300C38—H380.9300
C19—H190.9300C39—H390.9300
C5—N1—N2105.3 (3)C25—N21—N22106.1 (3)
C3—N2—N1112.2 (3)C23—N22—N21111.8 (3)
C3—N2—C6128.4 (3)C23—N22—C26128.6 (3)
N1—N2—C6119.4 (3)N21—N22—C26119.6 (3)
N2—C3—C4107.3 (3)N22—C23—C24107.1 (3)
N2—C3—H3126.4N22—C23—H23126.5
C4—C3—H3126.4C24—C23—H23126.5
C3—C4—C5104.7 (3)C23—C24—C25105.3 (3)
C3—C4—C12126.5 (3)C23—C24—C32124.8 (3)
C5—C4—C12128.3 (3)C25—C24—C32129.8 (3)
N1—C5—C4110.5 (3)N21—C25—C24109.7 (3)
N1—C5—C14119.1 (3)N21—C25—C34119.2 (3)
C4—C5—C14130.3 (3)C24—C25—C34131.1 (3)
C7—C6—C11120.5 (3)C27—C26—C31120.5 (4)
C7—C6—N2120.7 (3)C27—C26—N22121.2 (3)
C11—C6—N2118.8 (3)C31—C26—N22118.2 (3)
C6—C7—C8119.4 (4)C26—C27—C28119.7 (4)
C6—C7—H7120.3C26—C27—H27120.2
C8—C7—H7120.3C28—C27—H27120.2
C9—C8—C7120.9 (4)C29—C28—C27120.9 (4)
C9—C8—H8119.5C29—C28—H28119.5
C7—C8—H8119.5C27—C28—H28119.5
C8—C9—C10119.1 (4)C28—C29—C30118.7 (4)
C8—C9—H9120.4C28—C29—H29120.6
C10—C9—H9120.4C30—C29—H29120.6
C9—C10—C11120.9 (4)C29—C30—C31121.0 (4)
C9—C10—H10119.5C29—C30—H30119.5
C11—C10—H10119.5C31—C30—H30119.5
C6—C11—C10119.1 (4)C26—C31—C30119.1 (4)
C6—C11—H11120.4C26—C31—H31120.4
C10—C11—H11120.4C30—C31—H31120.4
O13—C12—C4125.6 (4)O33—C32—C24124.6 (4)
O13—C12—H12117.2O33—C32—H32117.7
C4—C12—H12117.2C24—C32—H32117.7
C15—C14—C19117.7 (4)C39—C34—C35117.1 (4)
C15—C14—C5122.1 (3)C39—C34—C25120.7 (3)
C19—C14—C5120.3 (3)C35—C34—C25122.2 (3)
C16—C15—C14121.7 (4)C36—C35—C34122.0 (4)
C16—C15—H15119.2C36—C35—H35119.0
C14—C15—H15119.2C34—C35—H35119.0
C17—C16—C15119.1 (4)C37—C36—C35119.7 (4)
C17—C16—H16120.5C37—C36—H36120.2
C15—C16—H16120.5C35—C36—H36120.2
C16—C17—C18121.3 (4)C36—C37—C38120.2 (4)
C16—C17—Br1119.3 (3)C36—C37—Br2119.7 (3)
C18—C17—Br1119.4 (3)C38—C37—Br2120.1 (3)
C19—C18—C17118.7 (4)C39—C38—C37119.5 (4)
C19—C18—H18120.6C39—C38—H38120.2
C17—C18—H18120.6C37—C38—H38120.2
C18—C19—C14121.5 (4)C38—C39—C34121.5 (4)
C18—C19—H19119.2C38—C39—H39119.2
C14—C19—H19119.2C34—C39—H39119.2
C5—N1—N2—C30.2 (4)C25—N21—N22—C230.8 (4)
C5—N1—N2—C6178.3 (3)C25—N21—N22—C26176.9 (3)
N1—N2—C3—C40.0 (4)N21—N22—C23—C240.8 (4)
C6—N2—C3—C4178.3 (4)C26—N22—C23—C24176.6 (4)
N2—C3—C4—C50.1 (4)N22—C23—C24—C250.5 (4)
N2—C3—C4—C12173.0 (4)N22—C23—C24—C32176.1 (4)
N2—N1—C5—C40.3 (4)N22—N21—C25—C240.5 (4)
N2—N1—C5—C14180.0 (3)N22—N21—C25—C34179.3 (3)
C3—C4—C5—N10.3 (4)C23—C24—C25—N210.0 (5)
C12—C4—C5—N1172.9 (4)C32—C24—C25—N21176.4 (4)
C3—C4—C5—C14180.0 (4)C23—C24—C25—C34178.6 (4)
C12—C4—C5—C147.4 (7)C32—C24—C25—C345.0 (7)
C3—N2—C6—C720.3 (6)C23—N22—C26—C275.3 (6)
N1—N2—C6—C7161.4 (4)N21—N22—C26—C27171.9 (4)
C3—N2—C6—C11158.2 (4)C23—N22—C26—C31178.0 (4)
N1—N2—C6—C1120.0 (5)N21—N22—C26—C314.7 (5)
C11—C6—C7—C80.4 (7)C31—C26—C27—C280.7 (7)
N2—C6—C7—C8178.1 (4)N22—C26—C27—C28177.3 (4)
C6—C7—C8—C91.5 (7)C26—C27—C28—C290.9 (8)
C7—C8—C9—C101.0 (8)C27—C28—C29—C300.4 (7)
C8—C9—C10—C110.6 (8)C28—C29—C30—C310.3 (7)
C7—C6—C11—C101.1 (7)C27—C26—C31—C300.0 (7)
N2—C6—C11—C10179.7 (4)N22—C26—C31—C30176.7 (4)
C9—C10—C11—C61.7 (7)C29—C30—C31—C260.5 (7)
C3—C4—C12—O136.5 (7)C23—C24—C32—O3311.3 (7)
C5—C4—C12—O13177.6 (4)C25—C24—C32—O33172.9 (4)
N1—C5—C14—C15139.7 (4)N21—C25—C34—C3926.1 (6)
C4—C5—C14—C1540.0 (6)C24—C25—C34—C39155.4 (4)
N1—C5—C14—C1939.7 (5)N21—C25—C34—C35152.2 (4)
C4—C5—C14—C19140.6 (4)C24—C25—C34—C3526.3 (7)
C19—C14—C15—C160.4 (6)C39—C34—C35—C360.5 (6)
C5—C14—C15—C16179.0 (4)C25—C34—C35—C36178.8 (4)
C14—C15—C16—C171.2 (7)C34—C35—C36—C371.6 (7)
C15—C16—C17—C181.5 (7)C35—C36—C37—C381.4 (7)
C15—C16—C17—Br1179.4 (3)C35—C36—C37—Br2179.8 (4)
C16—C17—C18—C191.0 (7)C36—C37—C38—C390.2 (7)
Br1—C17—C18—C19180.0 (3)Br2—C37—C38—C39179.0 (3)
C17—C18—C19—C140.1 (6)C37—C38—C39—C341.0 (7)
C15—C14—C19—C180.2 (6)C35—C34—C39—C380.8 (6)
C5—C14—C19—C18179.6 (4)C25—C34—C39—C38177.5 (4)

Experimental details

Crystal data
Chemical formulaC16H11BrN2O
Mr327.18
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)9.6716 (8), 11.4617 (9), 13.8257 (10)
α, β, γ (°)113.497 (5), 92.753 (6), 93.753 (6)
V3)1397.91 (19)
Z4
Radiation typeMo Kα
µ (mm1)2.94
Crystal size (mm)0.34 × 0.18 × 0.06
Data collection
DiffractometerStoe IPDS 2T
diffractometer
Absorption correctionMulti-scan
(MULABS; Blessing, 1995)
Tmin, Tmax0.477, 0.660
No. of measured, independent and
observed [I > 2σ(I)] reflections
14312, 6740, 2856
Rint0.063
(sin θ/λ)max1)0.661
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.158, 0.92
No. of reflections6740
No. of parameters361
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.52, 0.73

Computer programs: X-AREA (Stoe & Cie, 2010), X-RED (Stoe & Cie, 2010), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

 

Acknowledgements

This research was supported financially by the Lan­desgraduiertenförderung program of the Ministry of Science, Research and Arts of the state of Baden-Württemberg, Germany.

References

First citationAltomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.  Web of Science CrossRef CAS IUCr Journals
First citationBlessing, R. H. (1995). Acta Cryst. A51, 33–38.  CrossRef CAS Web of Science IUCr Journals
First citationElkady, M., Niess, R., Schaible, A. M., Bauer, J., Luderer, S., Ambrosi, G., Werz, O. & Laufer, S. A. (2012). J. Med. Chem. 55, 8958–8962.  Web of Science CrossRef CAS PubMed
First citationRathelot, P., Azas, N., El-Kashef, H., Delmas, F., Di Giorgio, C., Timon-David, P., Maldonado, J. & Vanelle, P. (2002). Eur. J. Med. Chem. 37, 671–679.  Web of Science CrossRef PubMed CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals
First citationStoe & Cie (2010). X-AREA and X-RED. Stoe & Cie GmbH, Darmstadt, Germany.

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds