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In the crystal structure of the title compound, C9H9N3, the asymmetric unit contains two independent mol­ecules. In the crystal structure, the mol­ecules are involved in networks of N—H...N hydrogen-bond inter­actions linking the N atoms from both the amino and the imino groups. The compound also demonstrates an inter­esting stacking formation of a secondary structure. Two crystallographically independent mol­ecules are connected in helical chains, with four mol­ecules per helical turn.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806002893/hg6296sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806002893/hg6296Isup2.hkl
Contains datablock I

CCDC reference: 298461

Key indicators

  • Single-crystal X-ray study
  • T = 105 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.051
  • wR factor = 0.097
  • Data-to-parameter ratio = 9.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT420_ALERT_2_C D-H Without Acceptor N3A - H3AA ... ? PLAT420_ALERT_2_C D-H Without Acceptor N3 - H3A ... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H9 .. C9A .. 2.81 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H10A .. C3A .. 2.89 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H3A .. C4 .. 2.83 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
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 27.50 From the CIF: _reflns_number_total 2012 Count of symmetry unique reflns 2016 Completeness (_total/calc) 99.80% 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 6 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 2 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 5 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-3-amino-1H-pyrazole top
Crystal data top
C9H9N3F(000) = 336
Mr = 159.19Dx = 1.330 Mg m3
Monoclinic, P21Melting point: 363(1) K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 11.973 (1) ÅCell parameters from 3218 reflections
b = 5.5395 (4) Åθ = 1.7–27.9°
c = 11.9869 (10) ŵ = 0.08 mm1
β = 90.158 (8)°T = 105 K
V = 795.02 (11) Å3Prism, colorless
Z = 40.35 × 0.30 × 0.25 mm
Data collection top
Oxford Diffraction Xcalibur
diffractometer
1795 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.039
Enhance (Oxford Diffraction) monochromatorθmax = 27.5°, θmin = 3.4°
Detector resolution: 16.3 pixels mm-1h = 1515
ω scansk = 67
7425 measured reflectionsl = 1515
2012 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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H-atom parameters constrained
S = 1.21 w = 1/[σ2(Fo2) + (0.03P)2 + 0.25P]
where P = (Fo2 + 2Fc2)/3
2012 reflections(Δ/σ)max = 0.006
217 parametersΔρmax = 0.23 e Å3
1 restraintΔρmin = 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
N1A0.54122 (17)0.5190 (4)0.16976 (18)0.0188 (5)
N2A0.51961 (19)0.3236 (4)0.2376 (2)0.0224 (5)
N3A0.3898 (2)0.2443 (5)0.3809 (2)0.0364 (7)
H3AA0.41760.09890.39110.044*
H3AB0.33340.29400.42180.044*
C3A0.4342 (2)0.3932 (6)0.3012 (2)0.0232 (6)
C4A0.4004 (2)0.6310 (6)0.2745 (3)0.0247 (7)
H4A0.34190.72170.30770.030*
C5A0.4698 (2)0.7019 (5)0.1907 (2)0.0244 (6)
H5A0.46820.85350.15360.029*
C6A0.6252 (2)0.5034 (5)0.0869 (2)0.0194 (6)
C7A0.6950 (2)0.3009 (5)0.0832 (2)0.0210 (6)
H7A0.68740.17530.13660.025*
C8A0.7758 (2)0.2861 (5)0.0000 (2)0.0246 (6)
H8A0.82340.14900.00310.030*
C9A0.7877 (2)0.4677 (6)0.0782 (2)0.0251 (7)
H9A0.84290.45550.13470.030*
C10A0.7186 (2)0.6673 (6)0.0734 (2)0.0245 (6)
H10A0.72690.79280.12670.029*
C11A0.6373 (2)0.6867 (5)0.0085 (2)0.0231 (6)
H11A0.59020.82450.01090.028*
N10.14705 (18)0.7487 (4)0.45151 (18)0.0194 (5)
N20.21034 (19)0.5520 (4)0.48515 (19)0.0208 (5)
N30.33173 (19)0.4753 (5)0.6372 (2)0.0274 (6)
H3A0.34170.32520.61530.033*
H3B0.36560.52870.69760.033*
C30.2625 (2)0.6277 (5)0.5766 (2)0.0209 (6)
C40.2347 (2)0.8694 (5)0.6035 (2)0.0254 (6)
H40.26080.96290.66470.031*
C50.1617 (2)0.9376 (5)0.5214 (2)0.0240 (6)
H50.12721.09140.51460.029*
C60.0780 (2)0.7331 (5)0.3558 (2)0.0190 (6)
C70.0857 (2)0.5343 (5)0.2851 (2)0.0229 (6)
H70.13800.40970.30030.027*
C80.0162 (2)0.5193 (6)0.1922 (2)0.0280 (7)
H80.02130.38350.14410.034*
C90.0605 (2)0.7004 (6)0.1690 (3)0.0280 (7)
H90.10760.68940.10530.034*
C100.0675 (2)0.8970 (6)0.2396 (3)0.0274 (7)
H100.12011.02110.22420.033*
C110.0012 (2)0.9160 (5)0.3330 (2)0.0233 (6)
H110.00411.05230.38070.028*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0200 (12)0.0150 (12)0.0214 (12)0.0008 (10)0.0015 (9)0.0015 (10)
N2A0.0266 (12)0.0171 (12)0.0236 (12)0.0024 (10)0.0024 (10)0.0021 (10)
N3A0.0415 (15)0.0235 (14)0.0443 (16)0.0072 (13)0.0229 (13)0.0053 (13)
C3A0.0252 (14)0.0207 (14)0.0237 (14)0.0011 (12)0.0003 (12)0.0034 (12)
C4A0.0210 (14)0.0212 (14)0.0320 (16)0.0050 (12)0.0009 (12)0.0049 (13)
C5A0.0239 (14)0.0162 (14)0.0330 (16)0.0024 (12)0.0022 (12)0.0005 (13)
C6A0.0217 (14)0.0180 (13)0.0183 (13)0.0028 (11)0.0039 (10)0.0012 (11)
C7A0.0266 (14)0.0168 (14)0.0196 (13)0.0004 (12)0.0005 (11)0.0015 (12)
C8A0.0251 (14)0.0222 (15)0.0266 (15)0.0040 (12)0.0008 (11)0.0042 (13)
C9A0.0253 (15)0.0295 (17)0.0205 (14)0.0058 (13)0.0015 (11)0.0046 (13)
C10A0.0297 (15)0.0233 (16)0.0207 (14)0.0066 (13)0.0042 (12)0.0047 (13)
C11A0.0248 (14)0.0202 (15)0.0242 (14)0.0008 (12)0.0064 (12)0.0034 (13)
N10.0220 (12)0.0156 (12)0.0207 (12)0.0011 (10)0.0029 (9)0.0001 (10)
N20.0207 (12)0.0191 (13)0.0224 (12)0.0011 (10)0.0020 (10)0.0003 (11)
N30.0305 (13)0.0220 (13)0.0298 (13)0.0009 (11)0.0096 (10)0.0024 (12)
C30.0168 (13)0.0218 (14)0.0243 (15)0.0020 (11)0.0024 (11)0.0013 (12)
C40.0303 (15)0.0215 (15)0.0244 (15)0.0010 (13)0.0020 (12)0.0047 (13)
C50.0278 (15)0.0203 (15)0.0240 (14)0.0010 (13)0.0053 (12)0.0017 (12)
C60.0183 (13)0.0206 (14)0.0182 (13)0.0033 (11)0.0031 (10)0.0020 (11)
C70.0234 (14)0.0191 (14)0.0262 (14)0.0005 (12)0.0035 (12)0.0002 (13)
C80.0302 (16)0.0258 (16)0.0281 (15)0.0060 (14)0.0011 (12)0.0037 (14)
C90.0228 (15)0.0310 (17)0.0301 (16)0.0065 (13)0.0032 (12)0.0040 (14)
C100.0221 (14)0.0274 (16)0.0327 (16)0.0014 (13)0.0015 (12)0.0056 (14)
C110.0268 (15)0.0180 (14)0.0252 (15)0.0003 (12)0.0081 (12)0.0008 (12)
Geometric parameters (Å, º) top
N1A—C5A1.350 (3)N1—C51.352 (4)
N1A—N2A1.379 (3)N1—N21.386 (3)
N1A—C6A1.418 (3)N1—C61.415 (3)
N2A—C3A1.334 (4)N2—C31.328 (4)
N3A—C3A1.371 (4)N3—C31.387 (4)
N3A—H3AA0.8800N3—H3A0.8800
N3A—H3AB0.8800N3—H3B0.8800
C3A—C4A1.415 (4)C3—C41.417 (4)
C4A—C5A1.363 (4)C4—C51.367 (4)
C4A—H4A0.9500C4—H40.9500
C5A—H5A0.9500C5—H50.9500
C6A—C11A1.392 (4)C6—C71.392 (4)
C6A—C7A1.399 (4)C6—C111.395 (4)
C7A—C8A1.394 (4)C7—C81.391 (4)
C7A—H7A0.9500C7—H70.9500
C8A—C9A1.383 (4)C8—C91.387 (4)
C8A—H8A0.9500C8—H80.9500
C9A—C10A1.382 (4)C9—C101.382 (5)
C9A—H9A0.9500C9—H90.9500
C10A—C11A1.388 (4)C10—C111.391 (4)
C10A—H10A0.9500C10—H100.9500
C11A—H11A0.9500C11—H110.9500
C5A—N1A—N2A111.1 (2)C5—N1—N2111.0 (2)
C5A—N1A—C6A128.8 (2)C5—N1—C6128.6 (2)
N2A—N1A—C6A120.0 (2)N2—N1—C6120.4 (2)
C3A—N2A—N1A104.8 (2)C3—N2—N1104.3 (2)
C3A—N3A—H3AA120.0C3—N3—H3A120.0
C3A—N3A—H3AB120.0C3—N3—H3B120.0
H3AA—N3A—H3AB120.0H3A—N3—H3B120.0
N2A—C3A—N3A121.5 (3)N2—C3—N3121.3 (3)
N2A—C3A—C4A111.1 (3)N2—C3—C4112.1 (3)
N3A—C3A—C4A127.4 (3)N3—C3—C4126.6 (3)
C5A—C4A—C3A105.1 (3)C5—C4—C3104.3 (3)
C5A—C4A—H4A127.4C5—C4—H4127.8
C3A—C4A—H4A127.4C3—C4—H4127.8
N1A—C5A—C4A108.0 (3)N1—C5—C4108.3 (3)
N1A—C5A—H5A126.0N1—C5—H5125.9
C4A—C5A—H5A126.0C4—C5—H5125.9
C11A—C6A—C7A120.0 (2)C7—C6—C11120.0 (2)
C11A—C6A—N1A120.3 (3)C7—C6—N1120.2 (2)
C7A—C6A—N1A119.7 (2)C11—C6—N1119.9 (3)
C8A—C7A—C6A119.1 (3)C8—C7—C6119.6 (3)
C8A—C7A—H7A120.5C8—C7—H7120.2
C6A—C7A—H7A120.5C6—C7—H7120.2
C9A—C8A—C7A121.0 (3)C9—C8—C7120.7 (3)
C9A—C8A—H8A119.5C9—C8—H8119.6
C7A—C8A—H8A119.5C7—C8—H8119.6
C10A—C9A—C8A119.4 (3)C10—C9—C8119.3 (3)
C10A—C9A—H9A120.3C10—C9—H9120.4
C8A—C9A—H9A120.3C8—C9—H9120.4
C9A—C10A—C11A120.8 (3)C9—C10—C11121.0 (3)
C9A—C10A—H10A119.6C9—C10—H10119.5
C11A—C10A—H10A119.6C11—C10—H10119.5
C10A—C11A—C6A119.7 (3)C10—C11—C6119.4 (3)
C10A—C11A—H11A120.2C10—C11—H11120.3
C6A—C11A—H11A120.2C6—C11—H11120.3
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3B···N2Ai0.882.273.021 (3)143
N3A—H3AB···N20.882.193.016 (3)156
C9—H9···C9Aii0.952.813.704 (4)157
C10A—H10A···C3Aiii0.952.893.513 (4)124
N3—H3A···C4iv0.882.833.574 (4)143
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x1, y, z; (iii) x+1, y+1/2, z; (iv) x, y1, z.
 

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