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Acta Cryst. (2007). E63, o3362
https://doi.org/10.1107/S1600536807031443
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1-(5-Bromo­pyrimidin-2-yl)-3-phenyl-1H-pyrazole-4-carbaldehyde

A. Thiruvalluvar, M. Subramanyam, B. Kalluraya and B. Lingappa
The molecule of the title compound, C14H9BrN4O, is planar, lying on a mirror plane. The mol­ecules are linked by C—H...N hydrogen bonds; intra­molecular C—H...N and C—H...O hydrogen bonds are also present. Furthermore, there is a short inter­molecular Br...O contact [2.869 (5) Å].
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031443/wn2161sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031443/wn2161Isup2.hkl
Contains datablock I

CCDC reference: 657656

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 160 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.086
  • wR factor = 0.238
  • Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found




Alert level B
PLAT431_ALERT_2_B Short Inter HL..A Contact  Br1    ..  O41     ..       2.87 Ang.


Alert level C
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          8
PLAT747_ALERT_1_C D...A   Calc    2.774(8), Rep     2.77400 ......    Missing su
              C32  -N2      1.555   1.555
PLAT747_ALERT_1_C D...A   Calc    3.037(8), Rep     3.03700 ......    Missing su
              C36  -O41     1.555   1.555
PLAT747_ALERT_1_C D...A   Calc    3.410(8), Rep     3.41000 ......    Missing su
              C41  -N11     1.555   2.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C14 H9 Br N4 O


   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check
Comment top

A literature survey shows that a large number of simple, N-bridged, nitrogen- and sulfur-containing heterocyclic compounds, containing the pyrimidine unit, are associated with diverse biological activities (Wichmann et al., 1999; El-Bendary et al., 1998; Kirpal, 1999; Tsuji & Ishikawa, 1994). Pyrazoles constitute an important class of heterocycles, which display interesting biological properties such as fungicidal, anti-inflammatory, anti-arthritic, antidepressant and antiviral activity. Many pyrazolines also find utility as polymer intermediates in industry (Mohan et al., 1989; Baraldi et al., 1996; Baraldi et al., 2003; Sanjay et al., 2006).

In the title compound, Fig. 1, C14H9BrN4O, the molecule is planar, lying on a mirror plane (Fig. 3). The molecules are linked by C—H···N hydrogen bonds; intramolecular C—H···N and C—H···O hydrogen bonds are also present. Furthermore, there is a short intermolecular contact between Br1 and O41ii [2.869 (5) Å; symmetry code: (ii) x, y, z - 1]. Recently a similar structure, 3-(4-chlorophenyl)-1- (4,6-dimethylpyrimidin-2-yl)-1H-pyrazole-4-carbaldehyde, has been published (Thiruvalluvar et al., 2007); however, it is not planar.

Related literature top

For related literature, see: Wichmann et al. (1999); El-Bendary et al. (1998); Kirpal (1999); Tsuji & Ishikawa (1994); Mohan et al. (1989); Baraldi et al. (1996, 2003); Sanjay et al., (2006); Thiruvalluvar et al. (2007).

Experimental top

To the Vilsmeier-Haack complex (3.22 g), prepared from DMF (20 ml) and POCl3 (3.64 g, 0.021 mol) at 273–278 K was added 1-phenylethanone- (5-bromopyrimidin-2-yl)hydrazone (2.2 g, 0.007 mol). The reaction mixture was stirred at 333–343 K for 4 h, and monitored by TLC. The contents were cooled, poured into ice cold water and neutralized with sodium carbonate. The product that separated was filtered and recrystallized from ethyl acetate to give yellow crystals (1.7 g, 71%).

Refinement top

H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95Å and Uiso = 1.2Ueq(C). The maximum residual electron density peak is located 1.53 Å from H35.

Structure description top

A literature survey shows that a large number of simple, N-bridged, nitrogen- and sulfur-containing heterocyclic compounds, containing the pyrimidine unit, are associated with diverse biological activities (Wichmann et al., 1999; El-Bendary et al., 1998; Kirpal, 1999; Tsuji & Ishikawa, 1994). Pyrazoles constitute an important class of heterocycles, which display interesting biological properties such as fungicidal, anti-inflammatory, anti-arthritic, antidepressant and antiviral activity. Many pyrazolines also find utility as polymer intermediates in industry (Mohan et al., 1989; Baraldi et al., 1996; Baraldi et al., 2003; Sanjay et al., 2006).

In the title compound, Fig. 1, C14H9BrN4O, the molecule is planar, lying on a mirror plane (Fig. 3). The molecules are linked by C—H···N hydrogen bonds; intramolecular C—H···N and C—H···O hydrogen bonds are also present. Furthermore, there is a short intermolecular contact between Br1 and O41ii [2.869 (5) Å; symmetry code: (ii) x, y, z - 1]. Recently a similar structure, 3-(4-chlorophenyl)-1- (4,6-dimethylpyrimidin-2-yl)-1H-pyrazole-4-carbaldehyde, has been published (Thiruvalluvar et al., 2007); however, it is not planar.

For related literature, see: Wichmann et al. (1999); El-Bendary et al. (1998); Kirpal (1999); Tsuji & Ishikawa (1994); Mohan et al. (1989); Baraldi et al. (1996, 2003); Sanjay et al., (2006); Thiruvalluvar et al. (2007).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. The packing of the title compound, viewed down the b axis. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted.
[Figure 3] Fig. 3. The packing of the title compound, viewed down the c axis. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted.
1-(5-Bromopyrimidin-2-yl)-3-phenyl-1H-pyrazole-4-carbaldehyde top
Crystal data top
C14H9BrN4OF(000) = 656
Mr = 329.15Dx = 1.688 Mg m−3
Monoclinic, C2/mMelting point: 444(1) K
Hall symbol: -C 2yMo Kα radiation, λ = 0.71073 Å
a = 15.1590 (3) ÅCell parameters from 12482 reflections
b = 6.4761 (2) Åθ = 2.0–30.0°
c = 13.1979 (3) ŵ = 3.17 mm−1
β = 90.584 (2)°T = 160 K
V = 1295.59 (6) Å3Block, light_brown
Z = 40.25 × 0.25 × 0.15 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer		2049 independent reflections
Radiation source: Nonius FR590 sealed tube generator1780 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromatorRint = 0.089
Detector resolution: 9 pixels mm-1θmax = 30.0°, θmin = 2.7°
φ and ω scans with κ offsetsh = −21→20
Absorption correction: multi-scan
(Blessing, 1995)		k = −9→9
Tmin = 0.433, Tmax = 0.628l = −18→18
17133 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.086H-atom parameters constrained
wR(F2) = 0.238 w = 1/[σ2(Fo2) + (0.1474P)2 + 3.886P]
where P = (Fo2 + 2Fc2)/3
S = 1.14(Δ/σ)max < 0.001
2049 reflectionsΔρmax = 1.63 e Å−3
122 parametersΔρmin = −0.83 e Å−3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.108 (11)
Crystal data top
C14H9BrN4OV = 1295.59 (6) Å3
Mr = 329.15Z = 4
Monoclinic, C2/mMo Kα radiation
a = 15.1590 (3) ŵ = 3.17 mm−1
b = 6.4761 (2) ÅT = 160 K
c = 13.1979 (3) Å0.25 × 0.25 × 0.15 mm
β = 90.584 (2)°
Data collection top
Nonius KappaCCD area-detector
diffractometer		2049 independent reflections
Absorption correction: multi-scan
(Blessing, 1995)		1780 reflections with I > 2σ(I)
Tmin = 0.433, Tmax = 0.628Rint = 0.089
17133 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0860 restraints
wR(F2) = 0.238H-atom parameters constrained
S = 1.14Δρmax = 1.63 e Å−3
2049 reflectionsΔρmin = −0.83 e Å−3
122 parameters
Special details top

Experimental. Solvent used: Ethyl Acetate Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.558 (2) Frames collected: 369 Seconds exposure per frame: 60 Degrees rotation per frame: 2.0 Crystal-Detector distance (mm): 30.0

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
Br10.15553 (4)0.00000−0.50849 (4)0.0521 (3)
O410.1309 (3)0.000000.2757 (4)0.0564 (16)
N10.2038 (3)0.00000−0.0627 (4)0.0334 (11)
N20.2841 (3)0.00000−0.0148 (4)0.0346 (11)
N110.1114 (3)0.00000−0.2023 (4)0.0360 (12)
N130.2685 (3)0.00000−0.2227 (4)0.0414 (14)
C30.2666 (3)0.000000.0824 (4)0.0330 (12)
C40.1719 (4)0.000000.1001 (4)0.0360 (14)
C50.1368 (4)0.000000.0038 (4)0.0373 (14)
C120.1947 (3)0.00000−0.1698 (4)0.0337 (14)
C140.2553 (4)0.00000−0.3235 (5)0.0433 (19)
C150.1725 (4)0.00000−0.3662 (4)0.0396 (16)
C160.1008 (4)0.00000−0.3018 (4)0.0397 (14)
C310.3420 (3)0.000000.1551 (4)0.0333 (12)
C320.4289 (4)0.000000.1154 (5)0.0407 (16)
C330.5010 (4)0.000000.1799 (6)0.0457 (18)
C340.4886 (4)0.000000.2839 (6)0.050 (2)
C350.4060 (4)0.000000.3233 (5)0.0437 (17)
C360.3306 (4)0.000000.2595 (4)0.0387 (14)
C410.1129 (4)0.000000.1855 (4)0.0437 (18)
H50.075750.00000−0.013110.0445*
H140.305030.00000−0.366650.0522*
H160.042860.00000−0.329850.0476*
H320.437270.000000.044170.0487*
H330.558970.000000.153200.0550*
H340.538430.000000.328180.0597*
H350.398940.000000.394710.0525*
H360.273060.000000.287480.0465*
H410.051710.000000.169040.0521*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0463 (5)0.0828 (7)0.0272 (4)0.0000−0.0017 (2)0.0000
O410.038 (2)0.101 (4)0.030 (2)0.0000−0.0030 (16)0.0000
N10.0271 (19)0.043 (2)0.030 (2)0.0000−0.0009 (15)0.0000
N20.0256 (18)0.051 (2)0.027 (2)0.0000−0.0044 (15)0.0000
N110.031 (2)0.050 (2)0.027 (2)0.0000−0.0002 (16)0.0000
N130.028 (2)0.067 (3)0.029 (2)0.0000−0.0018 (16)0.0000
C30.030 (2)0.039 (2)0.030 (2)0.0000−0.0008 (17)0.0000
C40.032 (2)0.051 (3)0.025 (2)0.0000−0.0023 (17)0.0000
C50.028 (2)0.054 (3)0.030 (2)0.0000−0.0014 (18)0.0000
C120.026 (2)0.039 (2)0.036 (3)0.0000−0.0010 (18)0.0000
C140.036 (3)0.064 (4)0.030 (3)0.00000.005 (2)0.0000
C150.042 (3)0.060 (3)0.017 (2)0.00000.0040 (18)0.0000
C160.035 (2)0.054 (3)0.030 (2)0.0000−0.0027 (19)0.0000
C310.028 (2)0.041 (2)0.031 (2)0.0000−0.0005 (17)0.0000
C320.030 (2)0.055 (3)0.037 (3)0.00000.001 (2)0.0000
C330.031 (2)0.062 (4)0.044 (3)0.0000−0.009 (2)0.0000
C340.032 (3)0.067 (4)0.051 (4)0.0000−0.014 (2)0.0000
C350.042 (3)0.057 (3)0.032 (3)0.0000−0.002 (2)0.0000
C360.037 (2)0.051 (3)0.028 (2)0.0000−0.0037 (19)0.0000
C410.030 (2)0.072 (4)0.029 (3)0.00000.0022 (19)0.0000
Geometric parameters (Å, º) top
Br1—C151.893 (5)C31—C321.423 (8)
O41—C411.219 (7)C31—C361.390 (7)
N1—N21.366 (7)C32—C331.379 (9)
N1—C51.349 (8)C33—C341.387 (11)
N1—C121.419 (7)C34—C351.361 (9)
N2—C31.313 (7)C35—C361.413 (9)
N11—C121.330 (7)C5—H50.9500
N11—C161.321 (7)C14—H140.9500
N13—C121.325 (7)C16—H160.9500
N13—C141.343 (8)C32—H320.9500
C3—C41.457 (8)C33—H330.9500
C3—C311.485 (7)C34—H340.9500
C4—C51.373 (8)C35—H350.9500
C4—C411.446 (8)C36—H360.9500
C14—C151.371 (9)C41—H410.9500
C15—C161.387 (8)
Br1···O41i2.869 (5)C31···N11x3.3709 (19)
Br1···O41ii2.869 (5)C31···N11vii3.3709 (19)
Br1···H36i3.2400C31···C12x3.2916 (12)
Br1···H36ii3.2400C31···N11viii3.3709 (19)
O41···Br1iii2.869 (5)C31···C12viii3.2916 (12)
O41···C363.037 (8)C31···N11ix3.3709 (19)
O41···Br1iv2.869 (5)C31···C12ix3.2916 (12)
O41···H16v2.7400C34···C16ix3.519 (3)
O41···H16vi2.7400C34···C16viii3.519 (3)
O41···H362.1600C34···C16vii3.519 (3)
N1···C3vii3.2797 (11)C34···C16x3.519 (3)
N1···C3viii3.2797 (11)C35···C15ix3.498 (3)
N1···C3ix3.2797 (11)C35···C16x3.2520 (8)
N1···C3x3.2797 (11)C35···C15viii3.498 (3)
N2···N132.752 (7)C35···C16vii3.2520 (8)
N2···C3ix3.444 (2)C35···C15vii3.498 (3)
N2···C3vii3.444 (2)C35···C15x3.498 (3)
N2···C3viii3.444 (2)C35···C16viii3.2520 (8)
N2···C3x3.444 (2)C35···C16ix3.2520 (8)
N11···C31x3.3709 (19)C36···C15ix3.532 (3)
N11···C36vii3.441 (3)C36···C14x3.594 (4)
N11···C41v3.410 (8)C36···C16viii3.445 (3)
N11···C31ix3.3709 (19)C36···C15viii3.532 (3)
N11···C41vi3.410 (8)C36···O413.037 (8)
N11···C36ix3.441 (3)C36···C12x3.468 (3)
N11···C31vii3.3709 (19)C36···C413.432 (8)
N11···C31viii3.3709 (19)C36···N11vii3.441 (3)
N11···C36viii3.441 (3)C36···N11viii3.441 (3)
N11···C36x3.441 (3)C36···C12vii3.468 (3)
N13···N22.752 (7)C36···C12viii3.468 (3)
N2···H322.4400C36···C14vii3.594 (4)
N11···H41vi2.5200C36···C14viii3.594 (4)
N11···H41v2.5200C36···C15vii3.532 (3)
N11···H52.5600C36···C14ix3.594 (4)
N13···H33xi2.7600C36···C16vii3.445 (3)
N13···H33xii2.7600C36···C12ix3.468 (3)
C3···N1vii3.2797 (11)C36···N11ix3.441 (3)
C3···N1viii3.2797 (11)C36···N11x3.441 (3)
C3···N2vii3.444 (2)C36···C16ix3.445 (3)
C3···N2viii3.444 (2)C36···C16x3.445 (3)
C3···C12vii3.485 (3)C36···C15x3.532 (3)
C3···C12viii3.485 (3)C41···C16vi3.599 (8)
C3···N1ix3.2797 (11)C41···C363.432 (8)
C3···N1x3.2797 (11)C41···C16v3.599 (8)
C3···N2ix3.444 (2)C41···N11v3.410 (8)
C3···N2x3.444 (2)C41···N11vi3.410 (8)
C3···C12ix3.485 (3)C4···H362.9000
C3···C12x3.485 (3)C16···H41v2.9200
C12···C3ix3.485 (3)C16···H41vi2.9200
C12···C3vii3.485 (3)C32···H32xi2.9400
C12···C3viii3.485 (3)C32···H32xii2.9400
C12···C31vii3.2916 (12)C41···H362.7600
C12···C31viii3.2916 (12)C41···H16v3.0500
C12···C36vii3.468 (3)C41···H16vi3.0500
C12···C36viii3.468 (3)H5···N112.5600
C12···C31x3.2916 (12)H5···H412.4400
C12···C3x3.485 (3)H5···H5v2.3300
C12···C31ix3.2916 (12)H5···H5vi2.3300
C12···C36ix3.468 (3)H14···H34xi2.4200
C12···C36x3.468 (3)H14···H34xii2.4200
C14···C36ix3.594 (4)H16···O41v2.7400
C14···C36vii3.594 (4)H16···C41v3.0500
C14···C36viii3.594 (4)H16···H41v2.5700
C14···C36x3.594 (4)H16···O41vi2.7400
C15···C35x3.498 (3)H16···C41vi3.0500
C15···C35vii3.498 (3)H16···H41vi2.5700
C15···C35viii3.498 (3)H32···N22.4400
C15···C36vii3.532 (3)H32···C32xi2.9400
C15···C36viii3.532 (3)H32···H32xi2.2400
C15···C35ix3.498 (3)H32···C32xii2.9400
C15···C36ix3.532 (3)H32···H32xii2.2400
C15···C36x3.532 (3)H33···N13xi2.7600
C16···C35vii3.2520 (8)H33···N13xii2.7600
C16···C41v3.599 (8)H34···H14xi2.4200
C16···C36vii3.445 (3)H34···H14xii2.4200
C16···C41vi3.599 (8)H36···Br1iii3.2400
C16···C34ix3.519 (3)H36···O412.1600
C16···C34vii3.519 (3)H36···C42.9000
C16···C34viii3.519 (3)H36···C412.7600
C16···C35x3.2520 (8)H36···Br1iv3.2400
C16···C35viii3.2520 (8)H41···H52.4400
C16···C36x3.445 (3)H41···N11v2.5200
C16···C36viii3.445 (3)H41···C16v2.9200
C16···C34x3.519 (3)H41···H16v2.5700
C16···C35ix3.2520 (8)H41···N11vi2.5200
C16···C36ix3.445 (3)H41···C16vi2.9200
C31···C12vii3.2916 (12)H41···H16vi2.5700
N2—N1—C5111.9 (5)C31—C32—C33120.3 (6)
N2—N1—C12122.6 (4)C32—C33—C34119.8 (6)
C5—N1—C12125.6 (5)C33—C34—C35120.8 (6)
N1—N2—C3105.3 (4)C34—C35—C36121.0 (6)
C12—N11—C16115.2 (5)C31—C36—C35118.9 (5)
C12—N13—C14113.8 (5)O41—C41—C4128.9 (6)
N2—C3—C4111.5 (4)N1—C5—H5126.00
N2—C3—C31118.0 (4)C4—C5—H5126.00
C4—C3—C31130.5 (5)N13—C14—H14119.00
C3—C4—C5103.0 (5)C15—C14—H14119.00
C3—C4—C41138.0 (5)N11—C16—H16119.00
C5—C4—C41119.0 (5)C15—C16—H16119.00
N1—C5—C4108.4 (5)C31—C32—H32120.00
N1—C12—N11113.8 (4)C33—C32—H32120.00
N1—C12—N13116.8 (4)C32—C33—H33120.00
N11—C12—N13129.4 (5)C34—C33—H33120.00
N13—C14—C15122.3 (6)C33—C34—H34120.00
Br1—C15—C14121.5 (5)C35—C34—H34120.00
Br1—C15—C16120.6 (4)C34—C35—H35120.00
C14—C15—C16117.9 (5)C36—C35—H35120.00
N11—C16—C15121.4 (5)C31—C36—H36121.00
C3—C31—C32118.1 (5)C35—C36—H36121.00
C3—C31—C36122.5 (5)O41—C41—H41116.00
C32—C31—C36119.3 (5)C4—C41—H41116.00
C5—N1—N2—C30.00 (1)N2—C3—C31—C320.00 (1)
C12—N1—N2—C3180.00 (1)N2—C3—C31—C36−180.00 (1)
N2—N1—C5—C40.00 (1)C4—C3—C31—C32180.00 (1)
C12—N1—C5—C4180.00 (1)C4—C3—C31—C360.00 (1)
N2—N1—C12—N11−180.00 (1)C3—C4—C5—N10.00 (1)
N2—N1—C12—N130.00 (1)C41—C4—C5—N1180.00 (1)
C5—N1—C12—N110.00 (1)C3—C4—C41—O410.00 (1)
C5—N1—C12—N13180.00 (1)C5—C4—C41—O41−180.00 (1)
N1—N2—C3—C40.00 (1)N13—C14—C15—Br1180.00 (1)
N1—N2—C3—C31−180.00 (1)N13—C14—C15—C160.00 (1)
C16—N11—C12—N1−180.00 (1)Br1—C15—C16—N11−180.00 (1)
C16—N11—C12—N130.00 (1)C14—C15—C16—N110.00 (1)
C12—N11—C16—C150.00 (1)C3—C31—C32—C33−180.00 (1)
C14—N13—C12—N1180.00 (1)C36—C31—C32—C330.00 (1)
C14—N13—C12—N110.00 (1)C3—C31—C36—C35−180.00 (1)
C12—N13—C14—C150.00 (1)C32—C31—C36—C350.00 (1)
N2—C3—C4—C50.00 (1)C31—C32—C33—C340.00 (1)
N2—C3—C4—C41−180.00 (1)C32—C33—C34—C350.00 (1)
C31—C3—C4—C5180.00 (1)C33—C34—C35—C360.00 (1)
C31—C3—C4—C410.00 (1)C34—C35—C36—C310.00 (1)
Symmetry codes: (i) x, y, z−1; (ii) x, −y, z−1; (iii) x, y, z+1; (iv) x, −y, z+1; (v) −x, y, −z; (vi) −x, −y, −z; (vii) −x+1/2, y−1/2, −z; (viii) −x+1/2, y+1/2, −z; (ix) −x+1/2, −y−1/2, −z; (x) −x+1/2, −y+1/2, −z; (xi) −x+1, y, −z; (xii) −x+1, −y, −z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C32—H32···N20.952.442.774100
C36—H36···O410.952.163.037153
C41—H41···N11v0.952.523.410157
Symmetry code: (v) −x, y, −z.

Experimental details

Crystal data
Chemical formulaC14H9BrN4O
Mr329.15
Crystal system, space groupMonoclinic, C2/m
Temperature (K)160
a, b, c (Å)15.1590 (3), 6.4761 (2), 13.1979 (3)
β (°) 90.584 (2)
V (Å3)1295.59 (6)
Z4
Radiation typeMo Kα
µ (mm−1)3.17
Crystal size (mm)0.25 × 0.25 × 0.15
Data collection
DiffractometerNonius KappaCCD area-detector
Absorption correctionMulti-scan
(Blessing, 1995)
Tmin, Tmax0.433, 0.628
No. of measured, independent and
observed [I > 2σ(I)] reflections		17133, 2049, 1780
Rint0.089
(sin θ/λ)max (Å−1)0.704
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.086, 0.238, 1.14
No. of reflections2049
No. of parameters122
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)1.63, −0.83

Computer programs: COLLECT (Nonius, 2000), DENZO–SMN (Otwinowski & Minor, 1997), DENZO–SMN and SCALEPACK (Otwinowski & Minor, 1997), DIRDIF99 (Beurskens et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C32—H32···N20.952.442.774100
C36—H36···O410.952.163.037153
C41—H41···N11i0.952.523.410157
Symmetry code: (i) −x, y, −z.
 

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