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A new polymorph of 3-phenyl­pyrazole, C9H8N2, is described. Whereas the already known polymorph has Z′ = 6, the new one has Z′ = 4. The pyrazole rings of the four mol­ecules in the asymmetric unit are connected by N—H...N hydrogen bonds to form cyclic four-membered clusters. In two pyrazole rings, it is the N atom in position 1 that carries the H atom, whereas in the other two the N atom in position 2 carries the H atom. There are no further short contacts between symmetry-equivalent clusters.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680301078X/lh6063sup1.cif
Contains datablocks 1, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680301078X/lh60631sup2.hkl
Contains datablock 1

CCDC reference: 214853

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.043
  • wR factor = 0.092
  • Data-to-parameter ratio = 14.0

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ADDSYM reports no extra symmetry








Comment top

Recently, we have reported the X-ray crystal structure analysis of 3-phenylpyrazole, C9H8N2, (1) (Haghiri et al., 2002). Here we describe the X-ray crystal structure analysis of a new polymorph of 3-phenylpyrazole, (1). Tris(1-pyrazolyl)borates (`scorpinates') were invented by Trofimenko more than 30 years ago and are today well established as ligands in coordination chemistry (Trofimenko, 1993). Scorpinates now find applications in a wide range of chemistry, from modelling the active site of metal–enzymes, through analytical chemistry and organic synthesis to catalysis and materials science (Edelmann, 2001).

Given this background, we are interested in the synthesis of transition metal complexes (3) with hydrotris(3-phenylpyrazol-1-yl)borate, (2), as the ligand (see Scheme). Therefore, we have prepared 3-phenylpyrazole as a starting material several times. A new polymorph of 3-phenylpyrazol was obtained after recrystallization from CH3OH instead of from CH2Cl2.

The asymmetric unit of (1) contains four independent molecules, labeled A to D. It is interesting to note, that in molecules A and B the N atoms in position 1 carries a H atom whereas in molecules C and D its the N atoms in position 2, which carries the H atom. The pyrazole and phenyl groups of each molecule are approximately planar. The angles between the planes of the pyrazole and phenyl rings are 10.7 (1), 17.4 (1), 16.9 (1) and 14.95 (6)° for molecules A to D, respectively. The crystal structure is built up by circular clusters of these four molecules which are held together by N—H.·N hydrogen bonds (Fig. 1 and Table 1).

Experimental top

The title compound was synthesized according to literature procedures (Buchner & Hachumian, 1902). X-ray quality crystals were obtained after recrystallization from CH3OH at ambient temperature.

Refinement top

All H atoms could be located by difference Fourier synthesis and were refined with fixed individual displacement parameters [Uiso(H) = 1.2Ueq(N,C)] using a riding model, with N—H = 0.88 Å and C—H = 0.95 Å.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991).

Figures top
[Figure 1] Fig. 1. Perspective view of the four-membered cluster of the title compound with the atom-numbering scheme; displacement ellipsoids are at the 50% probability level. H atoms bonded to C atoms have been omitted for clarity.
(1) top
Crystal data top
C9H8N2Z = 8
Mr = 144.17F(000) = 608
Triclinic, P1Dx = 1.226 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.5745 (13) ÅCell parameters from 7377 reflections
b = 10.3359 (12) Åθ = 3.5–25.2°
c = 17.132 (2) ŵ = 0.08 mm1
α = 85.693 (10)°T = 173 K
β = 75.609 (10)°Block, colourless
γ = 72.102 (10)°0.31 × 0.15 × 0.11 mm
V = 1562.7 (3) Å3
Data collection top
Stoe IPDS II two-circle
diffractometer
3329 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.059
Graphite monochromatorθmax = 25.2°, θmin = 3.7°
ω scansh = 1111
12794 measured reflectionsk = 1112
5573 independent reflectionsl = 2020
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)] = 0.043H-atom parameters constrained
wR(F2) = 0.092 w = 1/[σ2(Fo2) + (0.0337P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.88(Δ/σ)max < 0.001
5573 reflectionsΔρmax = 0.19 e Å3
398 parametersΔρmin = 0.20 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0084 (9)
Crystal data top
C9H8N2γ = 72.102 (10)°
Mr = 144.17V = 1562.7 (3) Å3
Triclinic, P1Z = 8
a = 9.5745 (13) ÅMo Kα radiation
b = 10.3359 (12) ŵ = 0.08 mm1
c = 17.132 (2) ÅT = 173 K
α = 85.693 (10)°0.31 × 0.15 × 0.11 mm
β = 75.609 (10)°
Data collection top
Stoe IPDS II two-circle
diffractometer
3329 reflections with I > 2σ(I)
12794 measured reflectionsRint = 0.059
5573 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.092H-atom parameters constrained
S = 0.88Δρmax = 0.19 e Å3
5573 reflectionsΔρmin = 0.20 e Å3
398 parameters
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
N1A0.72060 (19)0.50293 (18)0.66325 (10)0.0454 (4)
H1A0.76740.45850.69980.055*
N2A0.57164 (19)0.52776 (17)0.66703 (10)0.0415 (4)
C3A0.5439 (2)0.59738 (19)0.60057 (11)0.0350 (4)
C4A0.6783 (2)0.6170 (2)0.55374 (13)0.0447 (5)
H4A0.69200.66290.50360.054*
C5A0.7858 (2)0.5558 (2)0.59585 (13)0.0479 (5)
H5A0.88940.55170.57970.057*
C11A0.3918 (2)0.63991 (19)0.58505 (11)0.0354 (4)
C12A0.2654 (2)0.6299 (2)0.64409 (12)0.0419 (5)
H12A0.27690.59430.69570.050*
C13A0.1229 (2)0.6715 (2)0.62799 (13)0.0475 (5)
H13A0.03760.66510.66880.057*
C14A0.1045 (2)0.7216 (2)0.55360 (14)0.0469 (5)
H14A0.00690.74960.54290.056*
C15A0.2291 (2)0.7314 (2)0.49397 (13)0.0468 (5)
H15A0.21680.76570.44230.056*
C16A0.3710 (2)0.6912 (2)0.50986 (12)0.0411 (5)
H16A0.45560.69870.46890.049*
N1B0.87194 (19)0.23731 (19)0.81058 (11)0.0472 (4)
H1B0.83840.18290.78800.057*
N2B0.83500 (18)0.37365 (18)0.80097 (10)0.0415 (4)
C3B0.9092 (2)0.4191 (2)0.84500 (11)0.0389 (5)
C4B0.9933 (2)0.3095 (2)0.88281 (14)0.0501 (5)
H4B1.05580.31190.91760.060*
C5B0.9662 (3)0.1972 (2)0.85898 (14)0.0535 (6)
H5B1.00800.10600.87450.064*
C11B0.8919 (2)0.5653 (2)0.84920 (11)0.0397 (5)
C12B0.9943 (3)0.6094 (3)0.87726 (14)0.0533 (6)
H12B1.07730.54470.89290.064*
C13B0.9757 (3)0.7473 (3)0.88251 (16)0.0634 (7)
H13B1.04480.77650.90280.076*
C14B0.8584 (3)0.8413 (3)0.85864 (15)0.0576 (6)
H14B0.84850.93540.86040.069*
C15B0.7542 (3)0.7992 (2)0.83185 (14)0.0526 (6)
H15B0.67120.86450.81660.063*
C16B0.7711 (2)0.6625 (2)0.82739 (13)0.0443 (5)
H16B0.69920.63420.80910.053*
N1C0.7461 (2)0.10275 (18)0.71827 (11)0.0473 (4)
N2C0.59896 (19)0.15166 (17)0.71608 (10)0.0419 (4)
H2C0.53270.22000.74550.050*
C3C0.5673 (2)0.0821 (2)0.66291 (12)0.0396 (5)
C4C0.6999 (2)0.0170 (2)0.62927 (13)0.0479 (5)
H4C0.71410.08270.58980.057*
C5C0.8071 (3)0.0000 (2)0.66515 (14)0.0518 (6)
H5C0.91000.05370.65380.062*
C11C0.4156 (2)0.1170 (2)0.64758 (12)0.0409 (5)
C12C0.3744 (3)0.0244 (3)0.60911 (14)0.0557 (6)
H12C0.44590.06110.59190.067*
C13C0.2310 (3)0.0559 (3)0.59594 (15)0.0656 (7)
H13C0.20480.00780.56960.079*
C14C0.1264 (3)0.1784 (3)0.62062 (14)0.0598 (7)
H14C0.02760.19890.61200.072*
C15C0.1645 (2)0.2723 (3)0.65820 (13)0.0534 (6)
H15C0.09230.35770.67470.064*
C16C0.3083 (2)0.2415 (2)0.67172 (12)0.0444 (5)
H16C0.33370.30620.69770.053*
N1D0.4294 (2)0.34644 (18)0.84401 (10)0.0441 (4)
N2D0.42569 (18)0.47755 (17)0.82706 (10)0.0388 (4)
H2D0.45010.50950.77820.047*
C3D0.3795 (2)0.5528 (2)0.89507 (11)0.0356 (4)
C4D0.3518 (2)0.4660 (2)0.95892 (12)0.0473 (5)
H4D0.31770.48821.01470.057*
C5D0.3841 (3)0.3408 (2)0.92421 (13)0.0505 (6)
H5D0.37530.26080.95350.061*
C11D0.3621 (2)0.6986 (2)0.89432 (12)0.0405 (5)
C12D0.3446 (3)0.7645 (2)0.96551 (15)0.0571 (6)
H12D0.34550.71441.01430.069*
C13D0.3259 (3)0.9033 (3)0.9657 (2)0.0779 (8)
H13D0.31620.94691.01450.093*
C14D0.3214 (3)0.9777 (3)0.8964 (2)0.0749 (8)
H14D0.30641.07280.89710.090*
C15D0.3387 (3)0.9136 (3)0.82618 (18)0.0658 (7)
H15D0.33600.96500.77790.079*
C16D0.3599 (3)0.7758 (2)0.82422 (14)0.0510 (5)
H16D0.37310.73300.77460.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0458 (11)0.0523 (12)0.0402 (10)0.0132 (9)0.0165 (8)0.0025 (8)
N2A0.0441 (10)0.0432 (10)0.0361 (9)0.0084 (8)0.0141 (8)0.0024 (8)
C3A0.0388 (11)0.0352 (11)0.0321 (10)0.0113 (9)0.0093 (9)0.0017 (8)
C4A0.0462 (12)0.0525 (14)0.0405 (11)0.0225 (10)0.0125 (10)0.0102 (10)
C5A0.0424 (12)0.0583 (15)0.0478 (13)0.0226 (11)0.0108 (10)0.0032 (11)
C11A0.0408 (11)0.0306 (11)0.0356 (10)0.0101 (9)0.0106 (9)0.0012 (8)
C12A0.0436 (12)0.0455 (13)0.0359 (11)0.0140 (10)0.0082 (9)0.0036 (9)
C13A0.0378 (12)0.0529 (14)0.0494 (13)0.0148 (10)0.0034 (10)0.0032 (10)
C14A0.0378 (12)0.0440 (13)0.0604 (14)0.0089 (10)0.0180 (11)0.0011 (11)
C15A0.0516 (13)0.0433 (13)0.0480 (12)0.0129 (10)0.0195 (11)0.0055 (10)
C16A0.0437 (12)0.0424 (12)0.0382 (11)0.0141 (9)0.0110 (9)0.0035 (9)
N1B0.0430 (10)0.0498 (12)0.0499 (11)0.0127 (9)0.0143 (9)0.0012 (9)
N2B0.0371 (9)0.0469 (11)0.0417 (9)0.0130 (8)0.0111 (8)0.0002 (8)
C3B0.0304 (10)0.0515 (13)0.0336 (10)0.0107 (9)0.0070 (8)0.0012 (9)
C4B0.0463 (13)0.0568 (15)0.0520 (13)0.0135 (11)0.0235 (11)0.0015 (11)
C5B0.0502 (13)0.0516 (15)0.0570 (14)0.0066 (11)0.0224 (11)0.0065 (11)
C11B0.0335 (10)0.0536 (14)0.0310 (10)0.0151 (9)0.0026 (8)0.0021 (9)
C12B0.0441 (13)0.0636 (17)0.0570 (14)0.0183 (11)0.0179 (11)0.0003 (12)
C13B0.0604 (16)0.0708 (19)0.0744 (17)0.0364 (14)0.0213 (13)0.0040 (14)
C14B0.0612 (15)0.0499 (15)0.0636 (15)0.0239 (13)0.0085 (12)0.0023 (12)
C15B0.0481 (13)0.0510 (15)0.0563 (14)0.0145 (11)0.0091 (11)0.0013 (11)
C16B0.0387 (12)0.0505 (14)0.0459 (12)0.0155 (10)0.0113 (10)0.0004 (10)
N1C0.0421 (10)0.0401 (11)0.0589 (11)0.0087 (8)0.0152 (9)0.0006 (9)
N2C0.0410 (10)0.0348 (10)0.0498 (10)0.0084 (8)0.0123 (8)0.0066 (8)
C3C0.0475 (12)0.0373 (12)0.0368 (10)0.0166 (10)0.0105 (9)0.0014 (9)
C4C0.0543 (14)0.0407 (13)0.0473 (12)0.0105 (11)0.0117 (10)0.0073 (10)
C5C0.0475 (13)0.0405 (13)0.0613 (14)0.0044 (10)0.0128 (11)0.0010 (11)
C11C0.0444 (12)0.0483 (13)0.0326 (10)0.0202 (10)0.0061 (9)0.0013 (9)
C12C0.0605 (15)0.0607 (16)0.0534 (14)0.0262 (13)0.0139 (12)0.0102 (12)
C13C0.0716 (18)0.089 (2)0.0541 (15)0.0456 (17)0.0166 (13)0.0073 (14)
C14C0.0481 (14)0.094 (2)0.0464 (13)0.0339 (15)0.0120 (11)0.0029 (13)
C15C0.0398 (12)0.0731 (17)0.0457 (13)0.0171 (12)0.0065 (10)0.0011 (11)
C16C0.0438 (12)0.0523 (14)0.0389 (11)0.0186 (11)0.0070 (9)0.0031 (10)
N1D0.0512 (11)0.0414 (11)0.0434 (10)0.0150 (8)0.0171 (8)0.0017 (8)
N2D0.0422 (9)0.0400 (10)0.0333 (9)0.0111 (8)0.0094 (7)0.0015 (7)
C3D0.0313 (10)0.0434 (12)0.0318 (10)0.0104 (9)0.0077 (8)0.0003 (9)
C4D0.0566 (14)0.0582 (15)0.0308 (10)0.0234 (11)0.0096 (10)0.0024 (10)
C5D0.0635 (15)0.0522 (15)0.0430 (12)0.0273 (12)0.0162 (11)0.0103 (11)
C11D0.0297 (10)0.0442 (13)0.0451 (12)0.0083 (9)0.0063 (9)0.0057 (9)
C12D0.0586 (15)0.0569 (16)0.0531 (14)0.0083 (12)0.0157 (11)0.0138 (11)
C13D0.081 (2)0.0609 (19)0.089 (2)0.0083 (15)0.0219 (17)0.0312 (16)
C14D0.0654 (17)0.0417 (16)0.115 (3)0.0100 (13)0.0211 (17)0.0090 (16)
C15D0.0654 (17)0.0482 (16)0.0814 (19)0.0191 (13)0.0124 (14)0.0075 (14)
C16D0.0538 (14)0.0474 (14)0.0492 (13)0.0175 (11)0.0050 (11)0.0016 (10)
Geometric parameters (Å, º) top
N1A—C5A1.333 (3)N1C—C5C1.340 (3)
N1A—N2A1.355 (2)N1C—N2C1.352 (2)
N1A—H1A0.8800N2C—C3C1.345 (2)
N2A—C3A1.339 (2)N2C—H2C0.8800
C3A—C4A1.401 (3)C3C—C4C1.385 (3)
C3A—C11A1.472 (3)C3C—C11C1.471 (3)
C4A—C5A1.372 (3)C4C—C5C1.379 (3)
C4A—H4A0.9500C4C—H4C0.9500
C5A—H5A0.9500C5C—H5C0.9500
C11A—C16A1.393 (3)C11C—C16C1.393 (3)
C11A—C12A1.397 (3)C11C—C12C1.401 (3)
C12A—C13A1.389 (3)C12C—C13C1.382 (3)
C12A—H12A0.9500C12C—H12C0.9500
C13A—C14A1.371 (3)C13C—C14C1.369 (4)
C13A—H13A0.9500C13C—H13C0.9500
C14A—C15A1.389 (3)C14C—C15C1.385 (3)
C14A—H14A0.9500C14C—H14C0.9500
C15A—C16A1.383 (3)C15C—C16C1.389 (3)
C15A—H15A0.9500C15C—H15C0.9500
C16A—H16A0.9500C16C—H16C0.9500
N1B—C5B1.328 (3)N1D—C5D1.337 (3)
N1B—N2B1.351 (2)N1D—N2D1.356 (2)
N1B—H1B0.8800N2D—C3D1.351 (2)
N2B—C3B1.348 (2)N2D—H2D0.8800
C3B—C4B1.393 (3)C3D—C4D1.388 (3)
C3B—C11B1.474 (3)C3D—C11D1.464 (3)
C4B—C5B1.375 (3)C4D—C5D1.380 (3)
C4B—H4B0.9500C4D—H4D0.9500
C5B—H5B0.9500C5D—H5D0.9500
C11B—C16B1.389 (3)C11D—C12D1.390 (3)
C11B—C12B1.394 (3)C11D—C16D1.392 (3)
C12B—C13B1.388 (3)C12D—C13D1.390 (4)
C12B—H12B0.9500C12D—H12D0.9500
C13B—C14B1.367 (4)C13D—C14D1.367 (4)
C13B—H13B0.9500C13D—H13D0.9500
C14B—C15B1.386 (3)C14D—C15D1.366 (4)
C14B—H14B0.9500C14D—H14D0.9500
C15B—C16B1.378 (3)C15D—C16D1.378 (3)
C15B—H15B0.9500C15D—H15D0.9500
C16B—H16B0.9500C16D—H16D0.9500
C5A—N1A—N2A109.91 (17)C5C—N1C—N2C105.80 (17)
C5A—N1A—H1A125.0C3C—N2C—N1C110.97 (18)
N2A—N1A—H1A125.0C3C—N2C—H2C124.5
C3A—N2A—N1A107.10 (16)N1C—N2C—H2C124.5
N2A—C3A—C4A109.13 (17)N2C—C3C—C4C107.14 (18)
N2A—C3A—C11A121.33 (17)N2C—C3C—C11C121.89 (19)
C4A—C3A—C11A129.54 (18)C4C—C3C—C11C130.96 (19)
C5A—C4A—C3A105.24 (18)C5C—C4C—C3C105.38 (19)
C5A—C4A—H4A127.4C5C—C4C—H4C127.3
C3A—C4A—H4A127.4C3C—C4C—H4C127.3
N1A—C5A—C4A108.62 (18)N1C—C5C—C4C110.7 (2)
N1A—C5A—H5A125.7N1C—C5C—H5C124.6
C4A—C5A—H5A125.7C4C—C5C—H5C124.6
C16A—C11A—C12A118.21 (18)C16C—C11C—C12C118.1 (2)
C16A—C11A—C3A120.08 (18)C16C—C11C—C3C121.30 (18)
C12A—C11A—C3A121.71 (17)C12C—C11C—C3C120.6 (2)
C13A—C12A—C11A120.53 (19)C13C—C12C—C11C120.7 (2)
C13A—C12A—H12A119.7C13C—C12C—H12C119.6
C11A—C12A—H12A119.7C11C—C12C—H12C119.6
C14A—C13A—C12A120.5 (2)C14C—C13C—C12C120.4 (2)
C14A—C13A—H13A119.8C14C—C13C—H13C119.8
C12A—C13A—H13A119.8C12C—C13C—H13C119.8
C13A—C14A—C15A119.8 (2)C13C—C14C—C15C120.0 (2)
C13A—C14A—H14A120.1C13C—C14C—H14C120.0
C15A—C14A—H14A120.1C15C—C14C—H14C120.0
C16A—C15A—C14A120.0 (2)C14C—C15C—C16C120.0 (2)
C16A—C15A—H15A120.0C14C—C15C—H15C120.0
C14A—C15A—H15A120.0C16C—C15C—H15C120.0
C15A—C16A—C11A121.0 (2)C15C—C16C—C11C120.7 (2)
C15A—C16A—H16A119.5C15C—C16C—H16C119.6
C11A—C16A—H16A119.5C11C—C16C—H16C119.6
C5B—N1B—N2B110.24 (17)C5D—N1D—N2D105.44 (17)
C5B—N1B—H1B124.9C3D—N2D—N1D111.17 (16)
N2B—N1B—H1B124.9C3D—N2D—H2D124.4
C3B—N2B—N1B106.64 (16)N1D—N2D—H2D124.4
N2B—C3B—C4B109.33 (19)N2D—C3D—C4D106.78 (17)
N2B—C3B—C11B120.96 (18)N2D—C3D—C11D122.76 (17)
C4B—C3B—C11B129.70 (18)C4D—C3D—C11D130.44 (19)
C5B—C4B—C3B105.12 (18)C5D—C4D—C3D105.31 (18)
C5B—C4B—H4B127.4C5D—C4D—H4D127.3
C3B—C4B—H4B127.4C3D—C4D—H4D127.3
N1B—C5B—C4B108.7 (2)N1D—C5D—C4D111.29 (18)
N1B—C5B—H5B125.7N1D—C5D—H5D124.4
C4B—C5B—H5B125.7C4D—C5D—H5D124.4
C16B—C11B—C12B118.4 (2)C12D—C11D—C16D118.0 (2)
C16B—C11B—C3B120.92 (17)C12D—C11D—C3D119.9 (2)
C12B—C11B—C3B120.68 (19)C16D—C11D—C3D122.11 (19)
C13B—C12B—C11B120.4 (2)C11D—C12D—C13D120.4 (3)
C13B—C12B—H12B119.8C11D—C12D—H12D119.8
C11B—C12B—H12B119.8C13D—C12D—H12D119.8
C14B—C13B—C12B120.4 (2)C14D—C13D—C12D120.7 (3)
C14B—C13B—H13B119.8C14D—C13D—H13D119.7
C12B—C13B—H13B119.8C12D—C13D—H13D119.7
C13B—C14B—C15B120.0 (2)C15D—C14D—C13D119.3 (3)
C13B—C14B—H14B120.0C15D—C14D—H14D120.4
C15B—C14B—H14B120.0C13D—C14D—H14D120.4
C16B—C15B—C14B119.9 (2)C14D—C15D—C16D121.1 (3)
C16B—C15B—H15B120.1C14D—C15D—H15D119.5
C14B—C15B—H15B120.1C16D—C15D—H15D119.5
C15B—C16B—C11B121.01 (19)C15D—C16D—C11D120.6 (2)
C15B—C16B—H16B119.5C15D—C16D—H16D119.7
C11B—C16B—H16B119.5C11D—C16D—H16D119.7
C5A—N1A—N2A—C3A0.0 (2)C5C—N1C—N2C—C3C0.1 (2)
N1A—N2A—C3A—C4A0.0 (2)N1C—N2C—C3C—C4C0.2 (2)
N1A—N2A—C3A—C11A179.35 (16)N1C—N2C—C3C—C11C178.57 (18)
N2A—C3A—C4A—C5A0.0 (2)N2C—C3C—C4C—C5C0.3 (2)
C11A—C3A—C4A—C5A179.3 (2)C11C—C3C—C4C—C5C178.4 (2)
N2A—N1A—C5A—C4A0.1 (2)N2C—N1C—C5C—C4C0.1 (2)
C3A—C4A—C5A—N1A0.1 (2)C3C—C4C—C5C—N1C0.2 (3)
N2A—C3A—C11A—C16A169.01 (19)N2C—C3C—C11C—C16C15.8 (3)
C4A—C3A—C11A—C16A10.2 (3)C4C—C3C—C11C—C16C162.7 (2)
N2A—C3A—C11A—C12A10.7 (3)N2C—C3C—C11C—C12C163.2 (2)
C4A—C3A—C11A—C12A170.1 (2)C4C—C3C—C11C—C12C18.3 (3)
C16A—C11A—C12A—C13A0.7 (3)C16C—C11C—C12C—C13C0.3 (3)
C3A—C11A—C12A—C13A179.63 (19)C3C—C11C—C12C—C13C178.8 (2)
C11A—C12A—C13A—C14A0.7 (3)C11C—C12C—C13C—C14C0.2 (4)
C12A—C13A—C14A—C15A0.2 (3)C12C—C13C—C14C—C15C0.8 (4)
C13A—C14A—C15A—C16A0.3 (3)C13C—C14C—C15C—C16C0.8 (4)
C14A—C15A—C16A—C11A0.4 (3)C14C—C15C—C16C—C11C0.3 (3)
C12A—C11A—C16A—C15A0.1 (3)C12C—C11C—C16C—C15C0.3 (3)
C3A—C11A—C16A—C15A179.83 (18)C3C—C11C—C16C—C15C178.8 (2)
C5B—N1B—N2B—C3B0.0 (2)C5D—N1D—N2D—C3D0.2 (2)
N1B—N2B—C3B—C4B0.2 (2)N1D—N2D—C3D—C4D0.2 (2)
N1B—N2B—C3B—C11B178.90 (17)N1D—N2D—C3D—C11D178.70 (17)
N2B—C3B—C4B—C5B0.3 (2)N2D—C3D—C4D—C5D0.1 (2)
C11B—C3B—C4B—C5B178.8 (2)C11D—C3D—C4D—C5D178.43 (19)
N2B—N1B—C5B—C4B0.2 (3)N2D—N1D—C5D—C4D0.2 (2)
C3B—C4B—C5B—N1B0.3 (3)C3D—C4D—C5D—N1D0.1 (3)
N2B—C3B—C11B—C16B17.8 (3)N2D—C3D—C11D—C12D166.85 (19)
C4B—C3B—C11B—C16B160.7 (2)C4D—C3D—C11D—C12D15.0 (3)
N2B—C3B—C11B—C12B163.98 (19)N2D—C3D—C11D—C16D14.2 (3)
C4B—C3B—C11B—C12B17.6 (3)C4D—C3D—C11D—C16D163.9 (2)
C16B—C11B—C12B—C13B0.5 (3)C16D—C11D—C12D—C13D0.1 (3)
C3B—C11B—C12B—C13B178.8 (2)C3D—C11D—C12D—C13D179.1 (2)
C11B—C12B—C13B—C14B1.4 (4)C11D—C12D—C13D—C14D1.3 (4)
C12B—C13B—C14B—C15B2.4 (4)C12D—C13D—C14D—C15D1.4 (4)
C13B—C14B—C15B—C16B1.7 (4)C13D—C14D—C15D—C16D0.3 (4)
C14B—C15B—C16B—C11B0.2 (3)C14D—C15D—C16D—C11D0.9 (4)
C12B—C11B—C16B—C15B1.2 (3)C12D—C11D—C16D—C15D0.9 (3)
C3B—C11B—C16B—C15B179.5 (2)C3D—C11D—C16D—C15D178.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···N2B0.882.042.909 (2)168
N1B—H1B···N1C0.882.002.863 (2)165
N2C—H2C···N1D0.882.062.894 (3)158
N2D—H2D···N2A0.882.002.840 (2)160

Experimental details

Crystal data
Chemical formulaC9H8N2
Mr144.17
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)9.5745 (13), 10.3359 (12), 17.132 (2)
α, β, γ (°)85.693 (10), 75.609 (10), 72.102 (10)
V3)1562.7 (3)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.31 × 0.15 × 0.11
Data collection
DiffractometerStoe IPDS II two-circle
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
12794, 5573, 3329
Rint0.059
(sin θ/λ)max1)0.600
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.092, 0.88
No. of reflections5573
No. of parameters398
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.19, 0.20

Computer programs: X-AREA (Stoe & Cie, 2001), X-AREA, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Sheldrick, 1991).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···N2B0.882.042.909 (2)168
N1B—H1B···N1C0.882.002.863 (2)165
N2C—H2C···N1D0.882.062.894 (3)158
N2D—H2D···N2A0.882.002.840 (2)160
 

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