supplementary materials


ez2116 scheme

Acta Cryst. (2008). E64, o362    [ doi:10.1107/S1600536807067943 ]

4-(4-Bromophenylhydrazono)-1-(5-bromopyrimidin-2-yl)-3-methyl-2-pyrazolin-5-one

M. Subramanyam, B. Lingappa, A. Thiruvalluvar, R. J. Butcher and B. Kalluraya

Abstract top

The asymmetric unit of the title compound, C14H10Br2N6O, contains two crystallographically independent molecules. The pyrazole ring of one molecule makes dihedral angles of 22.0 (3) and 3.5 (3)° with the pyrimidine and benzene rings, respectively; the corresponding values in the other molecule are 9.2 (3) and 2.1 (3)°, respectively. The molecules are linked by N-H...O, C-H...N and C-H...Br hydrogen bonds.

Comment top

The chemistry of pyrimidine and its derivatives has been studied due to their diverse biological activities (Baraldi et al., 1996; Lingappa et al., 2006, 2007). Pyrazoles and their derivatives are found to be associated with diverse pharmacological activities. Pyrazoles constitute an important class of heterocycles, which display interesting biological properties such as fungicidal, anti-inflammatory, anti-arthritic, anti-depressant and antiviral activity (Baraldi et al., 2003; Kalluraya et al., 2001; Kalluraya & Rahiman, 1997). The title compound, has been analysed as part of our crystallographic studies on pyrimidine derivatives (Thiruvalluvar et al., 2007a,b; Thiruvalluvar, Subramanyam, Lingappa et al., 2007). The asymmetric unit of the title compound, C14H10Br2N6O, Fig. 1, contains two crystallographically independent molecules, A and B. The pyrazole ring of A makes dihedral angles of 22.0 (3)° and 3.5 (3)° with the pyrimidine ring and phenyl ring respectively; the corresponding values in molecule B are 9.2 (3)° and 2.1 (3)°. The molecules are linked by N—H···O, C—H···N and C—H···Br hydrogen bonds; see Fig. 2 and hydrogen bond table.

Related literature top

For related literature, see: Baraldi et al. (1996, 2003); Kalluraya & Rahiman (1997); Kalluraya et al. (2001); Lingappa et al. (2006, 2007). For a related crystal structure, see: Thiruvalluvar, Subramanyam, Kalluraya et al. (2007a,b); Thiruvalluvar, Subramanyam, Lingappa et al. (2007).

Experimental top

Ethyl-2-(4-bromohydrazono-3-oxobutanoate (3.2 g, 0.01 mol) was dissolved in glacial acetic acid (15 ml). To this a solution of 2-hydrazino-5-bromo-pyrimidine (1.9 g, 0.01 mol) in glacial acetic acid (20 ml) was added and the mixture was refluxed for 4 h in an oil bath. It was cooled and allowed to stand overnight. The separated solid was filtered, dried and then recrystallized from ethanol to give reddish flakes. Further recrystallization from ethyl acetate gave the yellowish red crystals suitable for X-ray analysis (3.0 g, 70%).

Refinement top

H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.88–0.98 Å and Uiso=1.2 or 1.5 times Ueq(C).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis CCD (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); 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 with the atomic numbering and 50% probability displacement ellipsoids. H atoms are shown as small spheres of arbitrary radius.
[Figure 2] Fig. 2. The packing of the title compound, viewed down the a axis. Dashed lines indicate hydrogen bonds.
4-(4-Bromophenylhydrazono)-1-(5-bromopyrimidin-2-yl)-3-methyl-2-pyrazolin-5-one top
Crystal data top
C14H10Br2N6OZ = 4
Mr = 438.08F000 = 856
Triclinic, P1Dx = 1.890 Mg m3
Hall symbol: -P 1Melting point: 534(1) K
a = 9.1647 (3) ÅMo Kα radiation
λ = 0.71073 Å
b = 12.2833 (5) ÅCell parameters from 5753 reflections
c = 14.0288 (5) Åθ = 4.6–32.4º
α = 86.532 (3)ºµ = 5.28 mm1
β = 84.218 (3)ºT = 200 (2) K
γ = 78.747 (3)ºPrism, pale-yellow
V = 1539.67 (10) Å30.44 × 0.39 × 0.28 mm
Data collection top
Oxford Diffraction Gemini
diffractometer
9542 independent reflections
Radiation source: fine-focus sealed tube6336 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.057
Detector resolution: 10.5081 pixels mm-1θmax = 32.5º
T = 200(2) Kθmin = 4.6º
φ and ω scansh = 13→13
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
k = 18→18
Tmin = 0.205, Tmax = 0.320l = 20→20
24958 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)] = 0.082H-atom parameters constrained
wR(F2) = 0.139  w = 1/[σ2(Fo2) + (0.0029P)2 + 9.1374P]
where P = (Fo2 + 2Fc2)/3
S = 1.25(Δ/σ)max < 0.001
9542 reflectionsΔρmax = 0.83 e Å3
415 parametersΔρmin = 0.64 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C14H10Br2N6Oγ = 78.747 (3)º
Mr = 438.08V = 1539.67 (10) Å3
Triclinic, P1Z = 4
a = 9.1647 (3) ÅMo Kα
b = 12.2833 (5) ŵ = 5.28 mm1
c = 14.0288 (5) ÅT = 200 (2) K
α = 86.532 (3)º0.44 × 0.39 × 0.28 mm
β = 84.218 (3)º
Data collection top
Oxford Diffraction Gemini
diffractometer
9542 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
6336 reflections with I > 2σ(I)
Tmin = 0.205, Tmax = 0.320Rint = 0.057
24958 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.082415 parameters
wR(F2) = 0.139H-atom parameters constrained
S = 1.25Δρmax = 0.83 e Å3
9542 reflectionsΔρmin = 0.64 e Å3
Special details top

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
Br10.25785 (9)0.06030 (5)0.13400 (5)0.0442 (2)
Br20.35450 (8)0.83940 (5)0.95346 (4)0.0376 (2)
O5A0.3522 (5)0.4304 (3)0.4711 (3)0.0337 (12)
N1A0.1660 (5)0.4635 (4)0.3613 (3)0.0230 (12)
N2A0.0409 (5)0.5473 (4)0.3440 (3)0.0233 (12)
N5A0.1545 (5)0.6383 (4)0.5533 (3)0.0236 (12)
N6A0.2645 (5)0.5980 (4)0.6055 (3)0.0272 (14)
N12A0.1363 (5)0.3829 (4)0.2204 (3)0.0269 (14)
N16A0.2742 (5)0.2773 (4)0.3423 (3)0.0283 (14)
C3A0.0276 (6)0.6191 (4)0.4112 (4)0.0241 (16)
C4A0.1428 (6)0.5855 (4)0.4762 (4)0.0249 (17)
C5A0.2370 (6)0.4835 (4)0.4405 (4)0.0251 (17)
C11A0.1945 (6)0.3696 (4)0.3045 (4)0.0233 (17)
C13A0.1549 (6)0.2918 (4)0.1690 (4)0.0256 (17)
C14A0.2345 (6)0.1912 (5)0.2024 (4)0.0267 (17)
C15A0.2941 (7)0.1879 (4)0.2893 (4)0.0294 (16)
C31A0.0912 (7)0.7199 (5)0.4167 (4)0.0310 (17)
C41A0.2811 (6)0.6529 (4)0.6887 (4)0.0218 (14)
C42A0.1781 (6)0.7470 (5)0.7170 (4)0.0269 (17)
C43A0.1993 (7)0.7997 (5)0.7976 (4)0.0289 (17)
C44A0.3238 (6)0.7582 (4)0.8478 (4)0.0240 (16)
C45A0.4250 (6)0.6644 (5)0.8210 (4)0.0274 (17)
C46A0.4032 (6)0.6110 (5)0.7402 (4)0.0268 (17)
Br30.35984 (7)0.28407 (6)0.22267 (5)0.0439 (2)
Br40.35687 (7)1.01017 (5)0.64977 (4)0.0352 (2)
O5B0.3253 (4)0.5890 (3)0.1841 (3)0.0289 (11)
N1B0.1528 (5)0.6272 (4)0.0654 (3)0.0242 (12)
N2B0.0319 (5)0.7132 (4)0.0455 (3)0.0257 (12)
N5B0.1476 (5)0.8095 (4)0.2504 (3)0.0243 (12)
N6B0.2564 (5)0.7670 (4)0.3048 (3)0.0255 (12)
N12B0.1135 (5)0.5468 (4)0.0740 (3)0.0246 (12)
N16B0.3245 (5)0.4721 (4)0.0142 (3)0.0297 (16)
C3B0.0199 (6)0.7867 (5)0.1108 (4)0.0257 (17)
C4B0.1306 (6)0.7519 (5)0.1779 (4)0.0243 (16)
C5B0.2192 (6)0.6457 (5)0.1473 (4)0.0225 (16)
C11B0.1992 (6)0.5427 (4)0.0014 (4)0.0221 (14)
C13B0.1610 (6)0.4687 (4)0.1378 (4)0.0253 (17)
C14B0.2899 (6)0.3913 (5)0.1295 (4)0.0280 (17)
C15B0.3703 (7)0.3965 (5)0.0520 (4)0.0337 (17)
C31B0.0924 (7)0.8914 (5)0.1110 (4)0.0378 (19)
C41B0.2806 (6)0.8256 (5)0.3837 (4)0.0248 (17)
C42B0.1926 (7)0.9294 (5)0.4041 (4)0.0326 (17)
C43B0.2166 (7)0.9838 (5)0.4834 (4)0.0327 (17)
C44B0.3283 (6)0.9332 (5)0.5407 (4)0.0261 (16)
C45B0.4170 (7)0.8313 (5)0.5212 (4)0.0281 (17)
C46B0.3920 (6)0.7777 (4)0.4417 (4)0.0258 (16)
H6A0.327960.537100.589140.0325*
H13A0.113170.296140.109260.0305*
H15A0.351030.119930.312180.0351*
H31A0.154090.722420.363790.0462*
H31B0.152610.717960.477940.0462*
H31C0.045570.786060.412020.0462*
H42A0.094630.774620.681620.0322*
H43A0.129710.863480.818560.0344*
H45A0.508000.636670.856790.0324*
H46A0.471630.546120.720370.0320*
H6B0.313530.702290.291950.0304*
H13B0.104270.466440.190440.0301*
H15B0.460750.344630.045810.0402*
H31D0.153620.893700.057230.0567*
H31E0.156570.894870.171420.0567*
H31F0.041340.954860.104450.0567*
H42B0.117010.962450.364000.0391*
H43B0.157751.054380.498280.0397*
H45B0.493130.798740.561110.0337*
H46B0.451840.707420.426840.0303*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0592 (4)0.0278 (3)0.0472 (4)0.0018 (3)0.0158 (3)0.0168 (3)
Br20.0477 (4)0.0328 (3)0.0341 (3)0.0035 (3)0.0141 (3)0.0127 (3)
O5A0.036 (2)0.031 (2)0.034 (2)0.0029 (19)0.0159 (19)0.0093 (18)
N1A0.026 (2)0.020 (2)0.023 (2)0.0008 (19)0.0097 (18)0.0067 (18)
N2A0.026 (2)0.018 (2)0.025 (2)0.0002 (19)0.0041 (18)0.0041 (18)
N5A0.028 (2)0.023 (2)0.020 (2)0.003 (2)0.0056 (18)0.0030 (18)
N6A0.033 (3)0.022 (2)0.025 (2)0.001 (2)0.005 (2)0.0042 (19)
N12A0.032 (3)0.023 (2)0.026 (2)0.001 (2)0.010 (2)0.0059 (19)
N16A0.035 (3)0.023 (2)0.025 (2)0.004 (2)0.011 (2)0.0035 (19)
C3A0.028 (3)0.020 (2)0.024 (3)0.003 (2)0.005 (2)0.001 (2)
C4A0.029 (3)0.021 (3)0.026 (3)0.007 (2)0.002 (2)0.004 (2)
C5A0.031 (3)0.022 (3)0.022 (3)0.003 (2)0.005 (2)0.000 (2)
C11A0.025 (3)0.022 (3)0.024 (3)0.005 (2)0.004 (2)0.005 (2)
C13A0.029 (3)0.025 (3)0.023 (3)0.002 (2)0.008 (2)0.004 (2)
C14A0.029 (3)0.029 (3)0.026 (3)0.012 (2)0.004 (2)0.008 (2)
C15A0.037 (3)0.016 (2)0.034 (3)0.002 (2)0.012 (3)0.000 (2)
C31A0.032 (3)0.029 (3)0.032 (3)0.002 (3)0.007 (2)0.007 (2)
C41A0.026 (3)0.021 (2)0.019 (2)0.005 (2)0.003 (2)0.002 (2)
C42A0.029 (3)0.025 (3)0.026 (3)0.001 (2)0.008 (2)0.001 (2)
C43A0.034 (3)0.021 (3)0.030 (3)0.002 (2)0.005 (2)0.008 (2)
C44A0.031 (3)0.023 (3)0.019 (2)0.006 (2)0.004 (2)0.003 (2)
C45A0.026 (3)0.033 (3)0.024 (3)0.005 (2)0.005 (2)0.005 (2)
C46A0.025 (3)0.029 (3)0.027 (3)0.004 (2)0.004 (2)0.006 (2)
Br30.0343 (3)0.0493 (4)0.0480 (4)0.0003 (3)0.0035 (3)0.0294 (3)
Br40.0448 (4)0.0345 (3)0.0278 (3)0.0061 (3)0.0067 (3)0.0123 (2)
O5B0.033 (2)0.029 (2)0.0251 (19)0.0004 (18)0.0116 (17)0.0067 (16)
N1B0.023 (2)0.023 (2)0.027 (2)0.0024 (19)0.0071 (18)0.0026 (19)
N2B0.024 (2)0.024 (2)0.027 (2)0.003 (2)0.0061 (19)0.0031 (19)
N5B0.026 (2)0.024 (2)0.023 (2)0.003 (2)0.0044 (18)0.0050 (18)
N6B0.028 (2)0.025 (2)0.023 (2)0.001 (2)0.0056 (19)0.0060 (18)
N12B0.026 (2)0.023 (2)0.025 (2)0.003 (2)0.0058 (18)0.0033 (18)
N16B0.030 (3)0.034 (3)0.023 (2)0.003 (2)0.0068 (19)0.006 (2)
C3B0.023 (3)0.026 (3)0.027 (3)0.000 (2)0.005 (2)0.004 (2)
C4B0.027 (3)0.027 (3)0.020 (2)0.006 (2)0.003 (2)0.006 (2)
C5B0.024 (3)0.027 (3)0.018 (2)0.007 (2)0.005 (2)0.001 (2)
C11B0.024 (3)0.021 (2)0.020 (2)0.000 (2)0.003 (2)0.002 (2)
C13B0.028 (3)0.024 (3)0.025 (3)0.005 (2)0.006 (2)0.004 (2)
C14B0.025 (3)0.029 (3)0.028 (3)0.001 (2)0.001 (2)0.010 (2)
C15B0.026 (3)0.038 (3)0.033 (3)0.009 (3)0.009 (2)0.007 (3)
C31B0.041 (4)0.039 (3)0.029 (3)0.009 (3)0.009 (3)0.011 (3)
C41B0.025 (3)0.027 (3)0.022 (3)0.003 (2)0.000 (2)0.007 (2)
C42B0.038 (3)0.031 (3)0.028 (3)0.000 (3)0.011 (3)0.003 (2)
C43B0.037 (3)0.028 (3)0.031 (3)0.002 (3)0.004 (3)0.009 (2)
C44B0.032 (3)0.029 (3)0.018 (2)0.008 (3)0.001 (2)0.002 (2)
C45B0.029 (3)0.032 (3)0.023 (3)0.003 (3)0.006 (2)0.002 (2)
C46B0.031 (3)0.021 (2)0.025 (3)0.004 (2)0.002 (2)0.003 (2)
Geometric parameters (Å, °) top
Br1—C14A1.888 (6)C41A—C46A1.390 (8)
Br2—C44A1.909 (5)C41A—C42A1.392 (8)
Br3—C14B1.888 (6)C42A—C43A1.385 (8)
Br4—C44B1.912 (6)C43A—C44A1.396 (8)
O5A—C5A1.230 (7)C44A—C45A1.376 (8)
O5B—C5B1.221 (7)C45A—C46A1.394 (8)
N1A—N2A1.414 (7)C13A—H13A0.9500
N1A—C11A1.409 (7)C15A—H15A0.9500
N1A—C5A1.400 (7)C31A—H31A0.9800
N2A—C3A1.310 (7)C31A—H31C0.9800
N5A—N6A1.307 (6)C31A—H31B0.9800
N5A—C4A1.318 (7)C42A—H42A0.9500
N6A—C41A1.418 (7)C43A—H43A0.9500
N12A—C11A1.331 (7)C45A—H45A0.9500
N12A—C13A1.342 (7)C46A—H46A0.9500
N16A—C11A1.335 (7)C3B—C4B1.440 (8)
N16A—C15A1.336 (7)C3B—C31B1.482 (9)
N6A—H6A0.8800C4B—C5B1.459 (8)
N1B—N2B1.411 (7)C13B—C14B1.374 (8)
N1B—C11B1.415 (7)C14B—C15B1.385 (8)
N1B—C5B1.403 (7)C41B—C46B1.388 (8)
N2B—C3B1.307 (7)C41B—C42B1.398 (9)
N5B—C4B1.312 (7)C42B—C43B1.389 (8)
N5B—N6B1.323 (6)C43B—C44B1.392 (8)
N6B—C41B1.414 (7)C44B—C45B1.379 (9)
N12B—C13B1.332 (7)C45B—C46B1.389 (8)
N12B—C11B1.340 (7)C13B—H13B0.9500
N16B—C15B1.332 (7)C15B—H15B0.9500
N16B—C11B1.326 (7)C31B—H31D0.9800
N6B—H6B0.8800C31B—H31E0.9800
C3A—C31A1.481 (8)C31B—H31F0.9800
C3A—C4A1.447 (8)C42B—H42B0.9500
C4A—C5A1.460 (7)C43B—H43B0.9500
C13A—C14A1.388 (8)C45B—H45B0.9500
C14A—C15A1.381 (8)C46B—H46B0.9500
Br1···Br2i3.7421 (9)C5B···N2A3.347 (7)
Br2···C15Bii3.746 (6)C11B···C45Ax3.527 (8)
Br2···Br1iii3.7421 (9)C11B···C44Ax3.578 (7)
Br2···C3Biv3.733 (6)C11B···N12Bv3.319 (7)
Br3···C31Bv3.740 (6)C13A···C42Aix3.405 (8)
Br3···N6Bvi3.536 (5)C13A···N12Bv3.193 (7)
Br3···C46Bvi3.659 (6)C13B···C41Ax3.467 (8)
Br4···C45Bvii3.721 (6)C13B···N2Bv3.244 (7)
Br4···C43A3.644 (6)C13B···N1Bv3.358 (7)
Br1···H31Dv2.9200C13B···C46Ax3.361 (8)
Br2···H15Bii2.8700C13B···N12Av3.245 (7)
Br3···H6Bvi3.0900C14B···C46Ax3.438 (8)
Br3···H46Bvi3.2000C15B···O5Bvi3.219 (7)
Br3···H31Ev3.1600C15B···Br2ii3.746 (6)
Br3···H31Av2.8800C31A···C5Aix3.493 (8)
Br4···H31Eviii3.1000C31A···N5B3.323 (8)
Br4···H15Aii2.9200C31B···Br3v3.740 (6)
O5A···N5A3.044 (6)C41A···C45B3.425 (8)
O5A···C46Bii3.375 (7)C41A···C13Biv3.467 (8)
O5A···N6A2.821 (6)C41B···C4A3.555 (8)
O5A···N16A2.917 (6)C42A···C13Aix3.405 (8)
O5B···N16B2.857 (6)C42A···C45B3.569 (8)
O5B···N5B3.022 (6)C43A···Br43.644 (6)
O5B···N6B2.782 (6)C44A···C11Biv3.578 (7)
O5B···C15Bvi3.219 (7)C45A···C11Biv3.527 (8)
O5B···N1A3.220 (6)C45B···Br4vii3.721 (6)
O5B···C46Aii3.344 (7)C45B···C41A3.425 (8)
O5A···H46Bii2.6800C45B···C42A3.569 (8)
O5A···H6A2.1400C46A···C13Biv3.361 (8)
O5A···H31Bix2.8400C46A···C14Biv3.438 (8)
O5B···H6B2.1000C46A···O5Bii3.344 (7)
O5B···H46Aii2.6500C46B···N5A3.250 (7)
O5B···H15Bvi2.8200C46B···O5Aii3.375 (7)
N1A···O5B3.220 (6)C46B···N6A3.372 (7)
N1B···C13Bv3.358 (7)C46B···C4A3.573 (7)
N2A···N12A2.698 (6)C46B···Br3vi3.659 (6)
N2A···C5B3.347 (7)C5A···H6A2.4900
N2A···C4Aix3.402 (7)C5A···H31Bix2.8700
N2B···N12B2.667 (6)C5B···H6B2.4700
N2B···C13Bv3.244 (7)C15A···H45Bii3.0400
N5A···C46B3.250 (7)C15B···H45Aii3.0400
N5A···O5A3.044 (6)C31A···H43Bviii3.0100
N5B···O5B3.022 (6)C42B···H31C3.0500
N5B···C31A3.323 (8)H6A···C5A2.4900
N5B···C3A3.411 (7)H6A···H46A2.3900
N6A···C46B3.372 (7)H6A···O5A2.1400
N6A···O5A2.821 (6)H6B···H46B2.3900
N6B···C4A3.404 (7)H6B···O5B2.1000
N6B···Br3vi3.536 (5)H6B···C5B2.4700
N6B···C3A3.233 (7)H6B···Br3vi3.0900
N6B···O5B2.782 (6)H13A···N2Bv2.6800
N12A···C13Bv3.245 (7)H13A···N12Bv2.6100
N12A···N12Bv3.188 (6)H13B···N12Av2.6400
N12A···N2A2.698 (6)H13B···N2Av2.6700
N12B···N2B2.667 (6)H15A···Br4ii2.9200
N12B···C13Av3.193 (7)H15B···O5Bvi2.8200
N12B···C11Bv3.319 (7)H15B···Br2ii2.8700
N12B···N12Av3.188 (6)H31A···Br3v2.8800
N12B···N12Bv3.120 (6)H31B···N16Aix2.6500
N16A···O5A2.917 (6)H31B···C5Aix2.8700
N16B···O5B2.857 (6)H31B···O5Aix2.8400
N2A···H13Bv2.6700H31C···N5B2.7700
N2B···H13Av2.6800H31C···C42B3.0500
N5A···H42A2.4800H31C···H43Bviii2.3900
N5B···H42B2.4900H31D···Br1v2.9200
N5B···H31C2.7700H31E···Br4viii3.1000
N12A···H13Bv2.6400H31E···Br3v3.1600
N12B···H13Av2.6100H31F···H43Aviii2.4900
N16A···H45Bii2.6300H42A···N5A2.4800
N16A···H31Bix2.6500H42B···N5B2.4900
N16B···H45Aii2.6200H43A···H31Fviii2.4900
C3A···N5B3.411 (7)H43B···H31Cviii2.3900
C3A···C4Aix3.436 (7)H43B···C31Aviii3.0100
C3A···C5Aix3.414 (8)H45A···C15Bii3.0400
C3A···N6B3.233 (7)H45A···N16Bii2.6200
C3B···Br2x3.733 (6)H45B···C15Aii3.0400
C4A···N6B3.404 (7)H45B···N16Aii2.6300
C4A···N2Aix3.402 (7)H46A···O5Bii2.6500
C4A···C41B3.555 (8)H46A···H6A2.3900
C4A···C46B3.573 (7)H46B···H6B2.3900
C4A···C3Aix3.436 (7)H46B···Br3vi3.2000
C5A···C31Aix3.493 (8)H46B···O5Aii2.6800
C5A···C3Aix3.414 (8)
N2A—N1A—C5A112.8 (4)H31B—C31A—H31C109.00
N2A—N1A—C11A117.8 (4)H31A—C31A—H31C109.00
C5A—N1A—C11A129.2 (5)C43A—C42A—H42A120.00
N1A—N2A—C3A106.9 (4)C41A—C42A—H42A121.00
N6A—N5A—C4A118.1 (5)C42A—C43A—H43A120.00
N5A—N6A—C41A119.7 (5)C44A—C43A—H43A120.00
C11A—N12A—C13A116.3 (5)C44A—C45A—H45A121.00
C11A—N16A—C15A115.1 (5)C46A—C45A—H45A121.00
C41A—N6A—H6A120.00C41A—C46A—H46A120.00
N5A—N6A—H6A120.00C45A—C46A—H46A120.00
N2B—N1B—C5B112.4 (4)N2B—C3B—C31B122.6 (5)
C5B—N1B—C11B129.1 (5)N2B—C3B—C4B110.7 (5)
N2B—N1B—C11B118.2 (4)C4B—C3B—C31B126.7 (5)
N1B—N2B—C3B107.2 (4)N5B—C4B—C5B128.2 (5)
N6B—N5B—C4B117.4 (5)N5B—C4B—C3B124.6 (5)
N5B—N6B—C41B119.9 (5)C3B—C4B—C5B107.2 (5)
C11B—N12B—C13B115.0 (5)O5B—C5B—C4B128.0 (5)
C11B—N16B—C15B114.9 (5)N1B—C5B—C4B102.5 (5)
C41B—N6B—H6B120.00O5B—C5B—N1B129.5 (5)
N5B—N6B—H6B120.00N12B—C11B—N16B128.5 (5)
N2A—C3A—C31A122.8 (5)N1B—C11B—N12B115.7 (5)
C4A—C3A—C31A126.4 (5)N1B—C11B—N16B115.8 (5)
N2A—C3A—C4A110.8 (5)N12B—C13B—C14B121.8 (5)
C3A—C4A—C5A106.9 (5)C13B—C14B—C15B117.9 (5)
N5A—C4A—C5A128.3 (5)Br3—C14B—C15B120.7 (4)
N5A—C4A—C3A124.9 (5)Br3—C14B—C13B121.4 (4)
O5A—C5A—C4A128.5 (5)N16B—C15B—C14B121.9 (6)
N1A—C5A—C4A102.7 (4)C42B—C41B—C46B120.3 (5)
O5A—C5A—N1A128.9 (5)N6B—C41B—C42B120.8 (5)
N1A—C11A—N16A116.1 (5)N6B—C41B—C46B118.9 (5)
N12A—C11A—N16A127.8 (5)C41B—C42B—C43B119.5 (6)
N1A—C11A—N12A116.2 (5)C42B—C43B—C44B118.9 (6)
N12A—C13A—C14A120.5 (5)Br4—C44B—C45B120.0 (4)
Br1—C14A—C15A120.0 (4)Br4—C44B—C43B117.7 (4)
C13A—C14A—C15A118.2 (5)C43B—C44B—C45B122.4 (5)
Br1—C14A—C13A121.8 (4)C44B—C45B—C46B118.2 (5)
N16A—C15A—C14A122.0 (5)C41B—C46B—C45B120.7 (5)
C42A—C41A—C46A121.2 (5)N12B—C13B—H13B119.00
N6A—C41A—C46A118.3 (5)C14B—C13B—H13B119.00
N6A—C41A—C42A120.5 (5)N16B—C15B—H15B119.00
C41A—C42A—C43A119.0 (5)C14B—C15B—H15B119.00
C42A—C43A—C44A119.4 (5)C3B—C31B—H31D109.00
Br2—C44A—C43A117.7 (4)C3B—C31B—H31E109.00
Br2—C44A—C45A120.3 (4)C3B—C31B—H31F109.00
C43A—C44A—C45A122.0 (5)H31D—C31B—H31E109.00
C44A—C45A—C46A118.6 (5)H31D—C31B—H31F109.00
C41A—C46A—C45A119.8 (5)H31E—C31B—H31F109.00
N12A—C13A—H13A120.00C41B—C42B—H42B120.00
C14A—C13A—H13A120.00C43B—C42B—H42B120.00
N16A—C15A—H15A119.00C42B—C43B—H43B121.00
C14A—C15A—H15A119.00C44B—C43B—H43B121.00
C3A—C31A—H31A109.00C44B—C45B—H45B121.00
H31A—C31A—H31B109.00C46B—C45B—H45B121.00
C3A—C31A—H31B109.00C41B—C46B—H46B120.00
C3A—C31A—H31C109.00C45B—C46B—H46B120.00
C5A—N1A—N2A—C3A1.5 (6)C15B—N16B—C11B—N1B176.9 (5)
C11A—N1A—N2A—C3A173.3 (5)N2A—C3A—C4A—N5A176.9 (5)
N2A—N1A—C5A—O5A175.7 (5)N2A—C3A—C4A—C5A1.9 (6)
N2A—N1A—C5A—C4A2.5 (6)C31A—C3A—C4A—N5A3.2 (9)
C11A—N1A—C5A—O5A10.3 (9)C31A—C3A—C4A—C5A178.0 (5)
C11A—N1A—C5A—C4A171.5 (5)N5A—C4A—C5A—O5A5.6 (10)
N2A—N1A—C11A—N12A22.2 (7)N5A—C4A—C5A—N1A176.2 (5)
N2A—N1A—C11A—N16A156.5 (5)C3A—C4A—C5A—O5A175.7 (6)
C5A—N1A—C11A—N12A164.1 (5)C3A—C4A—C5A—N1A2.6 (6)
C5A—N1A—C11A—N16A17.2 (8)N12A—C13A—C14A—Br1178.0 (4)
N1A—N2A—C3A—C4A0.4 (6)N12A—C13A—C14A—C15A0.3 (8)
N1A—N2A—C3A—C31A179.6 (5)C13A—C14A—C15A—N16A1.6 (9)
C4A—N5A—N6A—C41A179.7 (5)Br1—C14A—C15A—N16A176.7 (4)
N6A—N5A—C4A—C3A179.9 (5)N6A—C41A—C46A—C45A178.5 (5)
N6A—N5A—C4A—C5A1.3 (8)N6A—C41A—C42A—C43A178.8 (5)
N5A—N6A—C41A—C42A2.3 (8)C42A—C41A—C46A—C45A0.9 (9)
N5A—N6A—C41A—C46A177.0 (5)C46A—C41A—C42A—C43A0.5 (9)
C13A—N12A—C11A—N1A175.8 (5)C41A—C42A—C43A—C44A0.7 (9)
C13A—N12A—C11A—N16A2.8 (8)C42A—C43A—C44A—Br2176.1 (4)
C11A—N12A—C13A—C14A1.7 (8)C42A—C43A—C44A—C45A1.6 (9)
C15A—N16A—C11A—N1A177.0 (5)C43A—C44A—C45A—C46A1.2 (9)
C15A—N16A—C11A—N12A1.5 (9)Br2—C44A—C45A—C46A176.4 (4)
C11A—N16A—C15A—C14A0.8 (8)C44A—C45A—C46A—C41A0.0 (8)
C5B—N1B—C11B—N16B1.4 (8)N2B—C3B—C4B—N5B178.8 (5)
C11B—N1B—N2B—C3B173.3 (5)N2B—C3B—C4B—C5B0.8 (7)
N2B—N1B—C5B—O5B179.6 (6)C31B—C3B—C4B—N5B0.1 (9)
N2B—N1B—C5B—C4B0.4 (6)C31B—C3B—C4B—C5B178.0 (5)
C11B—N1B—C5B—O5B6.2 (10)N5B—C4B—C5B—O5B1.1 (10)
C11B—N1B—C5B—C4B173.0 (5)N5B—C4B—C5B—N1B178.2 (6)
N2B—N1B—C11B—N12B6.1 (7)C3B—C4B—C5B—O5B179.1 (6)
C5B—N1B—N2B—C3B0.9 (6)C3B—C4B—C5B—N1B0.2 (6)
C5B—N1B—C11B—N12B179.2 (5)N12B—C13B—C14B—Br3177.8 (4)
N2B—N1B—C11B—N16B171.7 (5)N12B—C13B—C14B—C15B0.1 (8)
N1B—N2B—C3B—C31B177.8 (5)Br3—C14B—C15B—N16B179.2 (4)
N1B—N2B—C3B—C4B1.0 (6)C13B—C14B—C15B—N16B1.3 (9)
C4B—N5B—N6B—C41B179.7 (5)N6B—C41B—C42B—C43B178.5 (5)
N6B—N5B—C4B—C3B178.9 (5)C46B—C41B—C42B—C43B0.6 (9)
N6B—N5B—C4B—C5B1.3 (9)N6B—C41B—C46B—C45B178.5 (5)
N5B—N6B—C41B—C42B1.3 (8)C42B—C41B—C46B—C45B0.6 (9)
N5B—N6B—C41B—C46B177.8 (5)C41B—C42B—C43B—C44B0.0 (9)
C13B—N12B—C11B—N16B0.7 (8)C42B—C43B—C44B—Br4179.5 (5)
C11B—N12B—C13B—C14B1.0 (8)C42B—C43B—C44B—C45B0.5 (9)
C13B—N12B—C11B—N1B178.1 (5)Br4—C44B—C45B—C46B179.5 (4)
C15B—N16B—C11B—N12B0.6 (8)C43B—C44B—C45B—C46B0.5 (9)
C11B—N16B—C15B—C14B1.6 (8)C44B—C45B—C46B—C41B0.1 (9)
Symmetry codes: (i) x, y−1, z−1; (ii) −x+1, −y+1, −z+1; (iii) x, y+1, z+1; (iv) x, y, z+1; (v) −x, −y+1, −z; (vi) −x+1, −y+1, −z; (vii) −x+1, −y+2, −z+1; (viii) −x, −y+2, −z+1; (ix) −x, −y+1, −z+1; (x) x, y, z−1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N6A—H6A···O5A0.882.142.821 (6)134
N6B—H6B···O5B0.882.102.782 (6)134
C13A—H13A···N12Bv0.952.613.193 (7)120
C15A—H15A···Br4ii0.952.923.761 (6)148
C15B—H15B···Br2ii0.952.873.746 (6)153
C31A—H31A···Br3v0.982.883.858 (6)173
C31B—H31D···Br1v0.982.923.862 (6)160
C45A—H45A···N16Bii0.952.623.539 (7)162
Symmetry codes: (v) −x, −y+1, −z; (ii) −x+1, −y+1, −z+1.
Table 1
Hydrogen-bond geometry (Å, °)
top
D—H···AD—HH···AD···AD—H···A
N6A—H6A···O5A0.882.142.821 (6)134
N6B—H6B···O5B0.882.102.782 (6)134
C13A—H13A···N12Bi0.952.613.193 (7)120
C15A—H15A···Br4ii0.952.923.761 (6)148
C15B—H15B···Br2ii0.952.873.746 (6)153
C31A—H31A···Br3i0.982.883.858 (6)173
C31B—H31D···Br1i0.982.923.862 (6)160
C45A—H45A···N16Bii0.952.623.539 (7)162
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z+1.
Acknowledgements top

RJB acknowledges the NSF-MRI program for funding to purchase the X-ray CCD diffractometer. AT thanks the UGC, India, for the award of a Minor Research Project [file No. MRP-2355/06(UGC-SERO), link No. 2355, 10/01/2007].

references
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