Literature DB >> 21201394

4-(4-Bromo-phenyl-hydrazono)-1-(5-bromo-pyrimidin-2-yl)-3-methyl-2-pyrazolin-5-one.

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

Abstract

The asymmetric unit of the title compound, C(14)H(10)Br(2)N(6)O, contains two crystallographically independent mol-ecules. The pyrazole ring of one mol-ecule makes dihedral angles of 22.0 (3) and 3.5 (3)° with the pyrimidine and benzene rings, respectively; the corresponding values in the other mol-ecule are 9.2 (3) and 2.1 (3)°, respectively. The mol-ecules are linked by N-H⋯O, C-H⋯N and C-H⋯Br hydrogen bonds.

Entities:  

Year:  2008        PMID： 21201394      PMCID： PMC2960163          DOI： 10.1107/S1600536807067943

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

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

Experimental

Crystal data

C14H10Br2N6O M = 438.08 Triclinic, a = 9.1647 (3) Å b = 12.2833 (5) Å c = 14.0288 (5) Å α = 86.532 (3)° β = 84.218 (3)° γ = 78.747 (3)° V = 1539.67 (10) Å3 Z = 4 Mo Kα radiation μ = 5.28 mm−1 T = 200 (2) K 0.44 × 0.39 × 0.28 mm

Data collection

Oxford Diffraction Gemini diffractometer Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.205, T max = 0.320 (expected range = 0.146–0.228) 24958 measured reflections 9542 independent reflections 6336 reflections with I > 2σ(I) R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.082 wR(F 2) = 0.139 S = 1.25 9542 reflections 415 parameters H-atom parameters constrained Δρmax = 0.83 e Å−3 Δρmin = −0.64 e Å−3 Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis CCD; 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 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807067943/ez2116sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536807067943/ez2116Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C14H10Br2N6OZ = 4
Mr = 438.08F000 = 856
Triclinic, P1Dx = 1.890 Mg m−3
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 mm−1
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
Oxford Diffraction Gemini diffractometer9542 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 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 Å−3
415 parametersΔρmin = −0.64 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
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.
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)
C31A−0.0912 (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)
C31B−0.0924 (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*
H31A−0.154090.722420.363790.0462*
H31B−0.152610.717960.477940.0462*
H31C−0.045570.786060.412020.0462*
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*
H13B0.104270.46644−0.190440.0301*
H15B0.460750.34463−0.045810.0402*
H31D−0.153620.893700.057230.0567*
H31E−0.156570.894870.171420.0567*
H31F−0.041340.954860.104450.0567*
H42B0.117010.962450.364000.0391*
H43B0.157751.054380.498280.0397*
H45B0.493130.798740.561110.0337*
H46B0.451840.707420.426840.0303*
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)
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—C3A−1.5 (6)C15B—N16B—C11B—N1B−176.9 (5)
C11A—N1A—N2A—C3A173.3 (5)N2A—C3A—C4A—N5A−176.9 (5)
N2A—N1A—C5A—O5A−175.7 (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—C5A−178.0 (5)
C11A—N1A—C5A—C4A−171.5 (5)N5A—C4A—C5A—O5A−5.6 (10)
N2A—N1A—C11A—N12A22.2 (7)N5A—C4A—C5A—N1A176.2 (5)
N2A—N1A—C11A—N16A−156.5 (5)C3A—C4A—C5A—O5A175.7 (6)
C5A—N1A—C11A—N12A−164.1 (5)C3A—C4A—C5A—N1A−2.6 (6)
C5A—N1A—C11A—N16A17.2 (8)N12A—C13A—C14A—Br1178.0 (4)
N1A—N2A—C3A—C4A−0.4 (6)N12A—C13A—C14A—C15A−0.3 (8)
N1A—N2A—C3A—C31A179.6 (5)C13A—C14A—C15A—N16A1.6 (9)
C4A—N5A—N6A—C41A179.7 (5)Br1—C14A—C15A—N16A−176.7 (4)
N6A—N5A—C4A—C3A179.9 (5)N6A—C41A—C46A—C45A178.5 (5)
N6A—N5A—C4A—C5A1.3 (8)N6A—C41A—C42A—C43A−178.8 (5)
N5A—N6A—C41A—C42A2.3 (8)C42A—C41A—C46A—C45A−0.9 (9)
N5A—N6A—C41A—C46A−177.0 (5)C46A—C41A—C42A—C43A0.5 (9)
C13A—N12A—C11A—N1A−175.8 (5)C41A—C42A—C43A—C44A0.7 (9)
C13A—N12A—C11A—N16A2.8 (8)C42A—C43A—C44A—Br2176.1 (4)
C11A—N12A—C13A—C14A−1.7 (8)C42A—C43A—C44A—C45A−1.6 (9)
C15A—N16A—C11A—N1A177.0 (5)C43A—C44A—C45A—C46A1.2 (9)
C15A—N16A—C11A—N12A−1.5 (9)Br2—C44A—C45A—C46A−176.4 (4)
C11A—N16A—C15A—C14A−0.8 (8)C44A—C45A—C46A—C41A0.0 (8)
C5B—N1B—C11B—N16B−1.4 (8)N2B—C3B—C4B—N5B178.8 (5)
C11B—N1B—N2B—C3B−173.3 (5)N2B—C3B—C4B—C5B0.8 (7)
N2B—N1B—C5B—O5B−179.6 (6)C31B—C3B—C4B—N5B0.1 (9)
N2B—N1B—C5B—C4B−0.4 (6)C31B—C3B—C4B—C5B−178.0 (5)
C11B—N1B—C5B—O5B−6.2 (10)N5B—C4B—C5B—O5B1.1 (10)
C11B—N1B—C5B—C4B173.0 (5)N5B—C4B—C5B—N1B−178.2 (6)
N2B—N1B—C11B—N12B−6.1 (7)C3B—C4B—C5B—O5B179.1 (6)
C5B—N1B—N2B—C3B0.9 (6)C3B—C4B—C5B—N1B−0.2 (6)
C5B—N1B—C11B—N12B−179.2 (5)N12B—C13B—C14B—Br3−177.8 (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—C4B−1.0 (6)C13B—C14B—C15B—N16B1.3 (9)
C4B—N5B—N6B—C41B179.7 (5)N6B—C41B—C42B—C43B178.5 (5)
N6B—N5B—C4B—C3B−178.9 (5)C46B—C41B—C42B—C43B−0.6 (9)
N6B—N5B—C4B—C5B−1.3 (9)N6B—C41B—C46B—C45B−178.5 (5)
N5B—N6B—C41B—C42B−1.3 (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—Br4−179.5 (5)
C11B—N12B—C13B—C14B−1.0 (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—C46B−0.5 (9)
C11B—N16B—C15B—C14B−1.6 (8)C44B—C45B—C46B—C41B−0.1 (9)
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
Table 1

Hydrogen-bond geometry (Å, °)

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) ; (ii) .

  3 in total

1.  SHELXL: high-resolution refinement.

Authors:  G M Sheldrick; T R Schneider
Journal:  Methods Enzymol       Date:  1997       Impact factor: 1.600

2.  Pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine derivatives: potent and selective A(2A) adenosine antagonists.

Authors:  P G Baraldi; B Cacciari; G Spalluto; M J Pineda de las Infantas y Villatoro; C Zocchi; S Dionisotti; E Ongini
Journal:  J Med Chem       Date:  1996-03-01       Impact factor: 7.446

3.  Design, synthesis, and biological evaluation of C9- and C2-substituted pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines as new A2A and A3 adenosine receptors antagonists.

Authors:  Pier Giovanni Baraldi; Francesca Fruttarolo; Mojgan Aghazadeh Tabrizi; Delia Preti; Romeo Romagnoli; Hussein El-Kashef; Allan Moorman; Katia Varani; Stefania Gessi; Stefania Merighi; Pier Andrea Borea
Journal:  J Med Chem       Date:  2003-03-27       Impact factor: 7.446
  3 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.