Download citation
Download citation
link to html
The structure of the title compound, C9H9N3, consists of discrete mol­ecules. The secondary structure is formed by mol­ecules linked by N—H...N hydrogen bonds into linear chains. In addition to the conventional hydrogen bonds, there are several weak inter­actions of the type N—H...C, and π stacking inter­actions of the type C—H...C.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680600290X/hg6297sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680600290X/hg6297Isup2.hkl
Contains datablock I

CCDC reference: 298462

Key indicators

  • Single-crystal X-ray study
  • T = 105 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.052
  • wR factor = 0.150
  • Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT420_ALERT_2_C D-H Without Acceptor N3 - H3A ... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H8 .. C3 .. 2.85 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H3C .. C8 .. 2.84 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Johnson & Burnett, 1996); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

1-Phenyl-5-amino-1H-pyrazole top
Crystal data top
C9H9N3F(000) = 672
Mr = 159.19Dx = 1.286 Mg m3
Monoclinic, C2/cMelting point: 315(1) K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 14.386 (3) ÅCell parameters from 1962 reflections
b = 14.056 (3) Åθ = 2.3–26.6°
c = 10.462 (2) ŵ = 0.08 mm1
β = 128.97 (3)°T = 105 K
V = 1644.8 (9) Å3Prism, colorless
Z = 80.35 × 0.30 × 0.30 mm
Data collection top
Oxford Diffraction Xcalibur
diffractometer
1289 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.048
Enhance (Oxford Diffraction) monochromatorθmax = 25.0°, θmin = 2.9°
Detector resolution: 16.3 pixels mm-1h = 1317
ω scansk = 1616
6395 measured reflectionsl = 1212
1447 independent reflections
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150H-atom parameters constrained
S = 1.24 w = 1/[σ2(Fo2) + (0.08P)2 + 0.5P]
where P = (Fo2 + 2Fc2)/3
1447 reflections(Δ/σ)max < 0.001
109 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.27 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.

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
N10.15119 (13)0.17150 (10)0.59566 (19)0.0216 (4)
N20.22494 (14)0.22388 (11)0.7388 (2)0.0268 (4)
N30.05751 (15)0.15777 (12)0.3606 (2)0.0338 (5)
H3A0.04140.11720.31290.041*
H3B0.13190.17470.31130.041*
C30.15000 (18)0.27681 (13)0.7413 (2)0.0284 (5)
H3C0.17490.32060.82670.034*
C40.03080 (18)0.26156 (13)0.6055 (2)0.0267 (5)
H40.03770.29100.58240.032*
C50.03370 (16)0.19483 (13)0.5124 (2)0.0224 (5)
C60.20184 (16)0.10683 (13)0.5499 (2)0.0218 (5)
C70.14489 (17)0.02078 (13)0.4752 (2)0.0258 (5)
H70.07470.00350.46010.031*
C80.19142 (17)0.03962 (13)0.4227 (2)0.0281 (5)
H80.15130.09730.36810.034*
C90.29591 (17)0.01613 (14)0.4497 (2)0.0298 (5)
H90.32740.05740.41340.036*
C100.35450 (18)0.06796 (14)0.5301 (2)0.0303 (5)
H100.42760.08320.55170.036*
C110.30724 (16)0.12985 (13)0.5789 (2)0.0261 (5)
H110.34700.18790.63220.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0201 (8)0.0227 (8)0.0193 (8)0.0021 (6)0.0111 (7)0.0012 (6)
N20.0268 (9)0.0277 (9)0.0218 (9)0.0057 (7)0.0133 (8)0.0050 (7)
N30.0216 (9)0.0378 (10)0.0252 (9)0.0055 (7)0.0066 (8)0.0070 (8)
C30.0338 (11)0.0271 (10)0.0271 (11)0.0040 (8)0.0205 (10)0.0066 (8)
C40.0272 (10)0.0277 (10)0.0272 (10)0.0027 (8)0.0180 (9)0.0013 (8)
C50.0218 (10)0.0235 (9)0.0201 (10)0.0000 (7)0.0122 (8)0.0030 (7)
C60.0247 (10)0.0215 (9)0.0163 (9)0.0038 (7)0.0115 (8)0.0041 (7)
C70.0282 (10)0.0227 (10)0.0256 (10)0.0011 (8)0.0164 (9)0.0029 (8)
C80.0320 (11)0.0227 (10)0.0243 (11)0.0039 (8)0.0152 (10)0.0022 (8)
C90.0333 (11)0.0290 (11)0.0261 (11)0.0107 (9)0.0182 (10)0.0049 (9)
C100.0268 (10)0.0348 (11)0.0302 (11)0.0048 (9)0.0184 (9)0.0045 (9)
C110.0248 (10)0.0249 (10)0.0251 (10)0.0007 (8)0.0139 (9)0.0009 (8)
Geometric parameters (Å, º) top
N1—C51.368 (2)C6—C111.384 (3)
N1—N21.383 (2)C6—C71.393 (3)
N1—C61.423 (2)C7—C81.390 (3)
N2—C31.324 (3)C7—H70.9500
N3—C51.377 (3)C8—C91.384 (3)
N3—H3A0.8800C8—H80.9500
N3—H3B0.8800C9—C101.387 (3)
C3—C41.393 (3)C9—H90.9500
C3—H3C0.9500C10—C111.385 (3)
C4—C51.372 (3)C10—H100.9500
C4—H40.9500C11—H110.9500
C5—N1—N2111.16 (15)C11—C6—N1119.91 (16)
C5—N1—C6128.91 (16)C7—C6—N1119.90 (17)
N2—N1—C6119.87 (15)C8—C7—C6119.51 (18)
C3—N2—N1103.94 (15)C8—C7—H7120.2
C5—N3—H3A120.0C6—C7—H7120.2
C5—N3—H3B120.0C9—C8—C7120.32 (18)
H3A—N3—H3B120.0C9—C8—H8119.8
N2—C3—C4112.89 (17)C7—C8—H8119.8
N2—C3—H3C123.6C8—C9—C10119.69 (18)
C4—C3—H3C123.6C8—C9—H9120.2
C5—C4—C3105.17 (17)C10—C9—H9120.2
C5—C4—H4127.4C11—C10—C9120.46 (18)
C3—C4—H4127.4C11—C10—H10119.8
N1—C5—C4106.80 (17)C9—C10—H10119.8
N1—C5—N3122.91 (17)C6—C11—C10119.76 (18)
C4—C5—N3130.21 (17)C6—C11—H11120.1
C11—C6—C7120.19 (17)C10—C11—H11120.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3B···N2i0.882.213.028 (2)155
C8—H8···C3ii0.952.853.695 (3)149
C3—H3C···C8iii0.952.843.759 (3)162
N3—H3A···C7iv0.882.743.475 (3)142
Symmetry codes: (i) x1/2, y+1/2, z1/2; (ii) x, y, z1/2; (iii) x+1/2, y+1/2, z+3/2; (iv) x, y, z+1/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds