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The title compound [systematic name: 7-(4-methyl­phenyl)­pyrazolo­[2,3-a]­pyrimidine-3-carbo­nitrile], C14H10N4, crystallizes in space group P212121. The pyrazolo­pyrimidine ring system is essentially planar and makes a dihedral angle of 42.3 (2)° with the benzene ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804015673/wn6260sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804015673/wn6260Isup2.hkl
Contains datablock I

CCDC reference: 248769

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.036
  • wR factor = 0.087
  • Data-to-parameter ratio = 8.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C3 ... 1.43 Ang. PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 6 C4 -C2 -C3 -N4 -0.90 0.10 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 7 C1 -C2 -C3 -N4 166.00 11.00 1.555 1.555 1.555 1.555
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.38 From the CIF: _reflns_number_total 1364 Count of symmetry unique reflns 1366 Completeness (_total/calc) 99.85% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 0 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

7-(4-Methylphenyl)pyrazolo[2,3-a]pyrimidine-3-carbonitrile top
Crystal data top
C14H10N4Dx = 1.367 Mg m3
Mr = 234.26Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 696 reflections
a = 7.404 (3) Åθ = 3.4–23.1°
b = 10.276 (4) ŵ = 0.09 mm1
c = 14.963 (5) ÅT = 293 K
V = 1138.4 (7) Å3Prism, yellow
Z = 40.26 × 0.22 × 0.18 mm
F(000) = 488
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer
1097 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.038
Graphite monochromatorθmax = 26.4°, θmin = 2.4°
φ and ω scansh = 94
6603 measured reflectionsk = 1212
1364 independent reflectionsl = 1618
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)] = 0.036H-atom parameters constrained
wR(F2) = 0.087 w = 1/[σ2(Fo2) + (0.0427P)2 + 0.1275P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
1364 reflectionsΔρmax = 0.14 e Å3
165 parametersΔρmin = 0.12 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.035 (4)
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
N10.0356 (3)0.48741 (19)0.57263 (12)0.0447 (5)
N20.1152 (3)0.52414 (18)0.49387 (12)0.0368 (5)
N30.1765 (3)0.44069 (19)0.34719 (13)0.0459 (5)
N40.0517 (4)0.1074 (2)0.39411 (16)0.0628 (7)
C10.0176 (4)0.3665 (2)0.55726 (17)0.0471 (6)
H10.07740.31580.59940.057*
C20.0251 (4)0.3226 (2)0.47122 (16)0.0429 (6)
C30.0183 (4)0.2020 (2)0.42924 (17)0.0464 (6)
C40.1112 (3)0.4263 (2)0.43020 (15)0.0388 (5)
C50.2399 (4)0.5571 (2)0.32872 (15)0.0476 (6)
H50.28270.57190.27120.057*
C60.2475 (3)0.6600 (2)0.38950 (15)0.0430 (6)
H60.29440.73980.37160.052*
C70.1863 (3)0.6445 (2)0.47547 (14)0.0360 (5)
C80.1957 (3)0.7464 (2)0.54441 (14)0.0366 (5)
C90.2463 (4)0.7203 (2)0.63219 (15)0.0442 (6)
H90.27040.63520.64980.053*
C100.2606 (4)0.8202 (2)0.69288 (15)0.0474 (6)
H100.29570.80140.75110.057*
C110.2241 (4)0.9484 (2)0.66965 (15)0.0440 (6)
C120.1738 (4)0.9728 (2)0.58231 (15)0.0450 (6)
H120.14841.05780.56500.054*
C130.1602 (3)0.8744 (2)0.52041 (15)0.0414 (6)
H130.12690.89370.46200.050*
C140.2359 (4)1.0580 (2)0.73653 (17)0.0595 (8)
H14A0.12041.06990.76460.089*
H14B0.27021.13670.70650.089*
H14C0.32451.03710.78110.089*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0496 (12)0.0465 (11)0.0381 (11)0.0023 (10)0.0068 (10)0.0017 (9)
N20.0374 (10)0.0382 (10)0.0348 (10)0.0004 (9)0.0025 (9)0.0002 (8)
N30.0473 (12)0.0515 (13)0.0390 (11)0.0006 (11)0.0025 (10)0.0056 (10)
N40.0706 (16)0.0488 (13)0.0690 (15)0.0117 (12)0.0016 (13)0.0038 (12)
C10.0483 (16)0.0445 (14)0.0486 (15)0.0041 (13)0.0037 (13)0.0043 (12)
C20.0452 (14)0.0395 (13)0.0438 (14)0.0001 (12)0.0026 (12)0.0008 (10)
C30.0468 (15)0.0415 (14)0.0511 (14)0.0017 (12)0.0018 (13)0.0027 (12)
C40.0373 (13)0.0389 (12)0.0402 (12)0.0059 (11)0.0052 (11)0.0039 (11)
C50.0508 (16)0.0567 (17)0.0354 (12)0.0045 (14)0.0045 (12)0.0006 (12)
C60.0443 (14)0.0469 (14)0.0378 (12)0.0035 (12)0.0008 (12)0.0036 (11)
C70.0322 (11)0.0390 (12)0.0367 (12)0.0007 (10)0.0025 (11)0.0030 (10)
C80.0352 (12)0.0387 (12)0.0358 (12)0.0006 (11)0.0003 (10)0.0005 (10)
C90.0527 (15)0.0390 (13)0.0408 (13)0.0029 (12)0.0010 (12)0.0029 (10)
C100.0585 (17)0.0506 (15)0.0331 (12)0.0016 (14)0.0009 (12)0.0005 (11)
C110.0466 (15)0.0463 (15)0.0392 (13)0.0067 (12)0.0075 (12)0.0061 (11)
C120.0492 (14)0.0360 (12)0.0499 (15)0.0031 (11)0.0029 (12)0.0027 (11)
C130.0455 (14)0.0412 (13)0.0376 (12)0.0064 (11)0.0022 (11)0.0048 (11)
C140.074 (2)0.0559 (16)0.0485 (14)0.0081 (16)0.0106 (15)0.0135 (13)
Geometric parameters (Å, º) top
N1—C11.323 (3)C7—C81.472 (3)
N1—N21.371 (2)C8—C131.388 (3)
N2—C71.372 (3)C8—C91.392 (3)
N2—C41.385 (3)C9—C101.375 (3)
N3—C51.314 (3)C9—H90.9300
N3—C41.341 (3)C10—C111.389 (3)
N4—C31.133 (3)C10—H100.9300
C1—C21.400 (3)C11—C121.382 (3)
C1—H10.9300C11—C141.509 (3)
C2—C41.385 (3)C12—C131.375 (3)
C2—C31.426 (3)C12—H120.9300
C5—C61.396 (3)C13—H130.9300
C5—H50.9300C14—H14A0.9600
C6—C71.373 (3)C14—H14B0.9600
C6—H60.9300C14—H14C0.9600
C1—N1—N2103.7 (2)C13—C8—C9118.5 (2)
N1—N2—C7125.9 (2)C13—C8—C7118.9 (2)
N1—N2—C4112.5 (2)C9—C8—C7122.5 (2)
C7—N2—C4121.6 (2)C10—C9—C8120.0 (2)
C5—N3—C4115.1 (2)C10—C9—H9120.0
N1—C1—C2113.3 (2)C8—C9—H9120.0
N1—C1—H1123.4C9—C10—C11121.9 (2)
C2—C1—H1123.4C9—C10—H10119.1
C4—C2—C1105.3 (2)C11—C10—H10119.1
C4—C2—C3125.2 (2)C12—C11—C10117.5 (2)
C1—C2—C3129.4 (2)C12—C11—C14120.5 (2)
N4—C3—C2178.5 (3)C10—C11—C14122.0 (2)
N3—C4—N2123.3 (2)C13—C12—C11121.5 (2)
N3—C4—C2131.4 (2)C13—C12—H12119.2
N2—C4—C2105.3 (2)C11—C12—H12119.2
N3—C5—C6124.5 (2)C12—C13—C8120.6 (2)
N3—C5—H5117.7C12—C13—H13119.7
C6—C5—H5117.7C8—C13—H13119.7
C7—C6—C5120.6 (2)C11—C14—H14A109.5
C7—C6—H6119.7C11—C14—H14B109.5
C5—C6—H6119.7H14A—C14—H14B109.5
N2—C7—C6114.8 (2)C11—C14—H14C109.5
N2—C7—C8121.2 (2)H14A—C14—H14C109.5
C6—C7—C8124.0 (2)H14B—C14—H14C109.5
C1—N1—N2—C7177.5 (2)C4—N2—C7—C61.6 (3)
C1—N1—N2—C40.0 (3)N1—N2—C7—C84.8 (3)
N2—N1—C1—C20.2 (3)C4—N2—C7—C8177.9 (2)
N1—C1—C2—C40.4 (3)C5—C6—C7—N21.8 (3)
N1—C1—C2—C3176.3 (3)C5—C6—C7—C8177.7 (2)
C4—C2—C3—N40.9 (1)N2—C7—C8—C13141.1 (2)
C1—C2—C3—N4166 (11)C6—C7—C8—C1339.5 (3)
C5—N3—C4—N22.4 (3)N2—C7—C8—C941.7 (3)
C5—N3—C4—C2175.6 (3)C6—C7—C8—C9137.7 (3)
N1—N2—C4—N3178.1 (2)C13—C8—C9—C100.2 (4)
C7—N2—C4—N30.5 (3)C7—C8—C9—C10177.0 (2)
N1—N2—C4—C20.2 (3)C8—C9—C10—C110.6 (4)
C7—N2—C4—C2177.8 (2)C9—C10—C11—C120.5 (4)
C1—C2—C4—N3177.8 (3)C9—C10—C11—C14178.7 (3)
C3—C2—C4—N31.7 (4)C10—C11—C12—C130.1 (4)
C1—C2—C4—N20.4 (3)C14—C11—C12—C13179.3 (2)
C3—C2—C4—N2176.5 (2)C11—C12—C13—C80.5 (4)
C4—N3—C5—C62.1 (4)C9—C8—C13—C120.4 (4)
N3—C5—C6—C70.1 (4)C7—C8—C13—C12177.7 (2)
N1—N2—C7—C6175.7 (2)
 

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