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The title compound, C15H13N3, was distinguished from its linear tricyclic isomer by X-ray structure analysis. Bond lengths and angles [e.g. N—N 1.355 (3) Å] are normal. The mol­ecules are associated by C—H...N hydrogen bonds to form ribbons.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802018780/bt6202sup1.cif
Contains datablocks 5, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802018780/bt62025sup2.hkl
Contains datablock 5

CCDC reference: 200769

Key indicators

  • Single-crystal X-ray study
  • T = 143 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.054
  • wR factor = 0.146
  • Data-to-parameter ratio = 12.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: DIF4 (Stoe, 1992); cell refinement: DIF4; data reduction: REDU4 (Stoe, 1992); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

2-Phenyl-7,8-dihydro-6H-cyclopenta[e]pyrazolo[1,5-a]pyrimidine top
Crystal data top
C15H13N3F(000) = 496
Mr = 235.28Dx = 1.359 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 7.006 (3) ÅCell parameters from 46 reflections
b = 8.702 (3) Åθ = 10–11.5°
c = 19.115 (4) ŵ = 0.08 mm1
β = 99.36 (3)°T = 143 K
V = 1149.9 (7) Å3Prism, colourless
Z = 40.60 × 0.25 × 0.15 mm
Data collection top
Stoe STADI-4
diffractometer
Rint = 0.031
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 3.2°
Graphite monochromatorh = 80
ω/θ scansk = 102
2717 measured reflectionsl = 2222
2032 independent reflections3 standard reflections every 60 min
1483 reflections with I > 2σ(I) intensity decay: none
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.063P)2 + 0.6661P]
where P = (Fo2 + 2Fc2)/3
2032 reflections(Δ/σ)max < 0.001
163 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.26 e Å3
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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 2.6873 (0.0037) x + 6.9739 (0.0042) y + 9.8488 (0.0089) z = 5.3799 (0.0054)

* -0.0077 (0.0017) N1 * -0.0160 (0.0018) C2 * -0.0027 (0.0019) C3 * 0.0237 (0.0018) N4 * 0.0032 (0.0019) C5 * -0.0536 (0.0021) C6 * 0.0540 (0.0023) C7 * -0.0046 (0.0021) C8 * -0.0037 (0.0021) C9 * -0.0161 (0.0021) C10 * 0.0097 (0.0018) N11 * 0.0138 (0.0021) C12

Rms deviation of fitted atoms = 0.0246

- 1.3297 (0.0080) x + 7.2217 (0.0064) y + 10.4864 (0.0181) z = 6.4722 (0.0064)

Angle to previous plane (with approximate e.s.d.) = 11.86 (0.11)

* 0.0060 (0.0017) C13 * -0.0076 (0.0019) C14 * 0.0021 (0.0020) C15 * 0.0049 (0.0020) C16 * -0.0065 (0.0020) C17 * 0.0010 (0.0018) C18

Rms deviation of fitted atoms = 0.0053

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
N10.4552 (3)0.3694 (2)0.40811 (10)0.0298 (5)
C20.6029 (4)0.4517 (3)0.38930 (12)0.0287 (6)
C30.7696 (4)0.4459 (3)0.44025 (13)0.0307 (6)
H30.88980.49480.43820.037*
N40.8263 (3)0.3070 (2)0.55670 (11)0.0336 (5)
C50.7385 (4)0.2151 (3)0.59576 (13)0.0341 (6)
H50.80850.17990.63960.041*
C60.4234 (4)0.0616 (3)0.61271 (13)0.0336 (6)
H6A0.41590.09910.66110.040*
H6B0.47590.04430.61600.040*
C70.2234 (4)0.0664 (3)0.56567 (15)0.0464 (7)
H7A0.12810.11530.59160.056*
H7B0.17880.03920.55250.056*
C80.2413 (4)0.1602 (3)0.49822 (14)0.0328 (6)
H8A0.22040.09450.45540.039*
H8B0.14820.24660.49170.039*
C90.4427 (3)0.2161 (3)0.51367 (13)0.0284 (6)
C100.5473 (4)0.1665 (3)0.57600 (12)0.0297 (6)
N110.5322 (3)0.3110 (2)0.47223 (10)0.0272 (5)
C120.7244 (4)0.3547 (3)0.49416 (13)0.0301 (6)
C130.5748 (4)0.5362 (3)0.32141 (12)0.0313 (6)
C140.3917 (4)0.5575 (3)0.28223 (13)0.0413 (7)
H140.28220.51260.29770.050*
C150.3684 (5)0.6441 (3)0.22054 (15)0.0496 (8)
H150.24250.65950.19440.060*
C160.5264 (5)0.7081 (3)0.19675 (15)0.0520 (8)
H160.50940.76770.15450.062*
C170.7090 (5)0.6852 (3)0.23461 (15)0.0482 (8)
H170.81830.72760.21800.058*
C180.7338 (4)0.6005 (3)0.29679 (14)0.0402 (7)
H180.86000.58610.32290.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0340 (12)0.0276 (10)0.0291 (11)0.0004 (9)0.0090 (9)0.0008 (9)
C20.0350 (14)0.0239 (12)0.0290 (12)0.0004 (10)0.0107 (11)0.0044 (10)
C30.0305 (13)0.0272 (12)0.0360 (13)0.0017 (11)0.0106 (11)0.0020 (11)
N40.0327 (12)0.0344 (11)0.0339 (11)0.0016 (9)0.0054 (9)0.0009 (9)
C50.0355 (14)0.0365 (14)0.0302 (13)0.0038 (12)0.0047 (11)0.0019 (11)
C60.0390 (15)0.0298 (13)0.0343 (13)0.0004 (11)0.0133 (11)0.0017 (11)
C70.0354 (16)0.0511 (17)0.0549 (18)0.0002 (13)0.0136 (14)0.0146 (15)
C80.0282 (13)0.0325 (13)0.0374 (13)0.0007 (11)0.0042 (11)0.0023 (11)
C90.0290 (13)0.0247 (12)0.0330 (13)0.0020 (10)0.0097 (10)0.0056 (10)
C100.0345 (14)0.0272 (12)0.0289 (12)0.0069 (11)0.0094 (11)0.0023 (10)
N110.0307 (11)0.0258 (10)0.0262 (10)0.0000 (8)0.0079 (9)0.0008 (8)
C120.0304 (13)0.0279 (12)0.0328 (13)0.0004 (11)0.0079 (11)0.0020 (10)
C130.0424 (15)0.0247 (12)0.0281 (12)0.0005 (11)0.0097 (11)0.0031 (10)
C140.0504 (18)0.0389 (15)0.0339 (14)0.0058 (13)0.0052 (13)0.0006 (12)
C150.065 (2)0.0478 (17)0.0317 (15)0.0062 (15)0.0043 (14)0.0011 (13)
C160.087 (3)0.0393 (16)0.0299 (14)0.0029 (17)0.0100 (16)0.0046 (12)
C170.072 (2)0.0350 (15)0.0436 (17)0.0043 (14)0.0273 (16)0.0044 (13)
C180.0501 (17)0.0331 (14)0.0401 (15)0.0012 (13)0.0156 (13)0.0021 (12)
Geometric parameters (Å, º) top
N1—C21.354 (3)C14—C151.387 (4)
N1—N111.355 (3)C15—C161.381 (5)
C2—C31.395 (3)C16—C171.378 (5)
C2—C131.477 (3)C17—C181.385 (4)
C3—C121.378 (3)C3—H30.9500
N4—C51.313 (3)C5—H50.9500
N4—C121.354 (3)C6—H6A0.9900
C5—C101.397 (4)C6—H6B0.9900
C6—C101.509 (3)C7—H7A0.9900
C6—C71.537 (4)C7—H7B0.9900
C7—C81.548 (4)C8—H8A0.9900
C8—C91.476 (3)C8—H8B0.9900
C9—C101.363 (3)C14—H140.9500
C9—N111.365 (3)C15—H150.9500
N11—C121.397 (3)C16—H160.9500
C13—C141.389 (4)C17—H170.9500
C13—C181.395 (4)C18—H180.9500
C2—N1—N11103.29 (19)C12—C3—H3127.0
N1—C2—C3112.6 (2)C2—C3—H3127.0
N1—C2—C13119.9 (2)N4—C5—H5118.4
C3—C2—C13127.5 (2)C10—C5—H5118.4
C12—C3—C2106.0 (2)C10—C6—H6A110.9
C5—N4—C12117.4 (2)C7—C6—H6A110.9
N4—C5—C10123.2 (2)C10—C6—H6B110.9
C10—C6—C7104.5 (2)C7—C6—H6B110.9
C6—C7—C8108.2 (2)H6A—C6—H6B108.9
C9—C8—C7102.2 (2)C6—C7—H7A110.1
C10—C9—N11117.8 (2)C8—C7—H7A110.1
C10—C9—C8115.5 (2)C6—C7—H7B110.1
N11—C9—C8126.7 (2)C8—C7—H7B110.1
C9—C10—C5119.7 (2)H7A—C7—H7B108.4
C9—C10—C6109.3 (2)C9—C8—H8A111.3
C5—C10—C6131.0 (2)C7—C8—H8A111.3
N1—N11—C9126.8 (2)C9—C8—H8B111.3
N1—N11—C12113.05 (19)C7—C8—H8B111.3
C9—N11—C12120.1 (2)H8A—C8—H8B109.2
N4—C12—C3133.2 (2)C15—C14—H14119.9
N4—C12—N11121.7 (2)C13—C14—H14119.9
C3—C12—N11105.1 (2)C16—C15—H15119.7
C14—C13—C18118.9 (2)C14—C15—H15119.7
C14—C13—C2121.3 (2)C17—C16—H16120.2
C18—C13—C2119.8 (2)C15—C16—H16120.2
C15—C14—C13120.1 (3)C16—C17—H17119.9
C16—C15—C14120.6 (3)C18—C17—H17119.9
C17—C16—C15119.6 (3)C17—C18—H18119.8
C16—C17—C18120.3 (3)C13—C18—H18119.8
C17—C18—C13120.5 (3)
N11—N1—C2—C30.1 (2)C8—C9—N11—C12179.8 (2)
N11—N1—C2—C13179.30 (19)C5—N4—C12—C3178.2 (3)
N1—C2—C3—C120.0 (3)C5—N4—C12—N111.3 (3)
C13—C2—C3—C12179.2 (2)C2—C3—C12—N4179.6 (3)
C12—N4—C5—C100.6 (4)C2—C3—C12—N110.0 (2)
C10—C6—C7—C86.1 (3)N1—N11—C12—N4179.7 (2)
C6—C7—C8—C95.4 (3)C9—N11—C12—N40.9 (3)
C7—C8—C9—C102.8 (3)N1—N11—C12—C30.0 (3)
C7—C8—C9—N11177.1 (2)C9—N11—C12—C3178.7 (2)
N11—C9—C10—C50.9 (3)N1—C2—C13—C1412.2 (3)
C8—C9—C10—C5179.1 (2)C3—C2—C13—C14166.9 (2)
N11—C9—C10—C6179.03 (19)N1—C2—C13—C18169.9 (2)
C8—C9—C10—C61.0 (3)C3—C2—C13—C1811.0 (4)
N4—C5—C10—C90.5 (4)C18—C13—C14—C151.3 (4)
N4—C5—C10—C6179.4 (2)C2—C13—C14—C15176.6 (2)
C7—C6—C10—C94.5 (3)C13—C14—C15—C161.0 (4)
C7—C6—C10—C5175.7 (2)C14—C15—C16—C170.2 (4)
C2—N1—N11—C9178.6 (2)C15—C16—C17—C181.0 (4)
C2—N1—N11—C120.1 (2)C16—C17—C18—C130.7 (4)
C10—C9—N11—N1178.4 (2)C14—C13—C18—C170.5 (4)
C8—C9—N11—N11.7 (4)C2—C13—C18—C17177.5 (2)
C10—C9—N11—C120.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···N4i0.952.623.548 (3)165
C7—H7A···N4ii0.992.693.464 (4)135
Symmetry codes: (i) x+2, y+1, z+1; (ii) x1, y, z.
 

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