Download citation
Download citation
link to html
In the title compound, C13H11N5OS2, the dihedral angle between the planes of the phenyl and pyrazole rings is 25.62 (2)°. The crystal packing is stablized by intra- and inter­molecular hydrogen bonds which link the mol­ecules into a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806003990/rz6172sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806003990/rz6172Isup2.hkl
Contains datablock I

CCDC reference: 601239

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.037
  • wR factor = 0.095
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.09 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.76 Ratio PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C4 ... 1.42 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; 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.

1-Benzoyl-3-(4-cyano-5-methylsulfanyl-1H-pyrazol-3-yl)thiourea top
Crystal data top
C13H11N5OS2F(000) = 656
Mr = 317.39Dx = 1.454 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3337 reflections
a = 7.6970 (11) Åθ = 2.6–26.2°
b = 15.892 (2) ŵ = 0.37 mm1
c = 12.0775 (17) ÅT = 294 K
β = 100.999 (2)°Plate, light yellow
V = 1450.2 (3) Å30.34 × 0.28 × 0.24 mm
Z = 4
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
2938 independent reflections
Radiation source: fine-focus sealed tube2287 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
φ and ω scansθmax = 26.3°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 69
Tmin = 0.882, Tmax = 0.914k = 1919
8039 measured reflectionsl = 1514
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0403P)2 + 0.7311P]
where P = (Fo2 + 2Fc2)/3
2938 reflections(Δ/σ)max = 0.001
212 parametersΔρmax = 0.30 e Å3
20 restraintsΔρmin = 0.34 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*/UeqOcc. (<1)
S10.88574 (9)0.39786 (4)0.61584 (7)0.0688 (2)
S20.20987 (6)0.27316 (3)0.37905 (5)0.03952 (16)
O10.33366 (17)0.00581 (8)0.41396 (13)0.0420 (4)
N10.8393 (2)0.25986 (11)0.48282 (16)0.0420 (4)
N20.7313 (2)0.19593 (10)0.43960 (15)0.0377 (4)
N30.4438 (2)0.15222 (10)0.45187 (14)0.0327 (4)
H30.471 (3)0.0999 (14)0.4560 (17)0.037 (6)*
N40.1561 (2)0.10974 (10)0.38200 (14)0.0334 (4)
H40.057 (3)0.1259 (13)0.3480 (18)0.037 (6)*
N50.3860 (3)0.34654 (14)0.66339 (18)0.0588 (5)
C10.7680 (3)0.31268 (12)0.54738 (18)0.0392 (5)
C20.5990 (2)0.28199 (12)0.54778 (17)0.0347 (4)
C30.5847 (2)0.21005 (11)0.47907 (16)0.0313 (4)
C40.4775 (3)0.31706 (13)0.60991 (18)0.0406 (5)
C50.7599 (10)0.4839 (3)0.5434 (13)0.093 (3)0.80 (3)
H5A0.77540.48540.46640.139*0.80 (3)
H5B0.80040.53590.57980.139*0.80 (3)
H5C0.63680.47630.54540.139*0.80 (3)
C5'0.734 (3)0.4834 (13)0.588 (3)0.074 (7)0.20 (3)
H5'A0.69290.49810.65560.111*0.20 (3)
H5'B0.63440.46700.53090.111*0.20 (3)
H5'C0.79130.53090.56180.111*0.20 (3)
C60.2776 (2)0.17441 (11)0.40699 (16)0.0301 (4)
C70.1860 (2)0.02368 (12)0.38411 (16)0.0310 (4)
C80.0260 (2)0.02926 (11)0.34655 (15)0.0302 (4)
C90.1456 (2)0.00075 (13)0.34472 (17)0.0371 (5)
H90.16470.05430.36580.045*
C100.2875 (3)0.05441 (14)0.31153 (19)0.0459 (5)
H100.40210.03540.31040.055*
C110.2593 (3)0.13603 (14)0.28015 (19)0.0502 (6)
H110.35510.17190.25800.060*
C120.0900 (3)0.16441 (14)0.2816 (2)0.0529 (6)
H120.07160.21940.26010.064*
C130.0523 (3)0.11168 (13)0.31484 (18)0.0422 (5)
H130.16650.13130.31610.051*
H10.936 (3)0.2632 (15)0.4668 (19)0.049 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0526 (4)0.0480 (4)0.0980 (6)0.0173 (3)0.0057 (4)0.0157 (3)
S20.0287 (3)0.0291 (3)0.0585 (3)0.00116 (19)0.0026 (2)0.0062 (2)
O10.0273 (7)0.0330 (7)0.0631 (10)0.0022 (6)0.0017 (6)0.0031 (7)
N10.0249 (9)0.0418 (10)0.0603 (12)0.0047 (8)0.0107 (8)0.0010 (8)
N20.0295 (8)0.0356 (9)0.0481 (10)0.0014 (7)0.0077 (7)0.0020 (7)
N30.0249 (8)0.0256 (8)0.0458 (10)0.0002 (6)0.0021 (7)0.0009 (7)
N40.0232 (8)0.0277 (8)0.0461 (10)0.0014 (6)0.0012 (7)0.0024 (7)
N50.0529 (12)0.0686 (14)0.0547 (12)0.0084 (10)0.0099 (10)0.0187 (11)
C10.0314 (10)0.0328 (10)0.0507 (13)0.0027 (8)0.0007 (9)0.0004 (9)
C20.0279 (10)0.0332 (10)0.0419 (11)0.0002 (8)0.0037 (8)0.0030 (8)
C30.0255 (9)0.0305 (10)0.0363 (10)0.0002 (7)0.0015 (8)0.0024 (8)
C40.0356 (11)0.0396 (11)0.0434 (12)0.0011 (9)0.0007 (9)0.0070 (9)
C50.096 (4)0.040 (2)0.143 (6)0.000 (2)0.026 (4)0.002 (3)
C5'0.076 (10)0.067 (9)0.079 (11)0.006 (7)0.016 (7)0.010 (7)
C60.0276 (9)0.0299 (9)0.0331 (10)0.0020 (7)0.0067 (8)0.0006 (8)
C70.0304 (10)0.0305 (10)0.0319 (10)0.0000 (7)0.0055 (8)0.0000 (8)
C80.0326 (10)0.0284 (9)0.0295 (9)0.0018 (7)0.0055 (8)0.0003 (7)
C90.0337 (10)0.0332 (10)0.0457 (12)0.0024 (8)0.0106 (9)0.0025 (9)
C100.0315 (11)0.0518 (13)0.0547 (13)0.0065 (9)0.0088 (9)0.0002 (10)
C110.0458 (13)0.0477 (13)0.0530 (14)0.0199 (10)0.0010 (10)0.0039 (10)
C120.0590 (15)0.0351 (11)0.0589 (15)0.0054 (10)0.0032 (12)0.0141 (10)
C130.0388 (11)0.0376 (11)0.0478 (12)0.0025 (9)0.0019 (9)0.0082 (9)
Geometric parameters (Å, º) top
S1—C11.747 (2)C5—H5A0.9600
S1—C5'1.784 (10)C5—H5B0.9600
S1—C51.803 (5)C5—H5C0.9600
S2—C61.6677 (19)C5'—H5'A0.9600
O1—C71.219 (2)C5'—H5'B0.9600
N1—C11.333 (3)C5'—H5'C0.9600
N1—N21.353 (2)C7—C81.489 (2)
N1—H10.80 (2)C8—C131.390 (3)
N2—C31.325 (2)C8—C91.393 (3)
N3—C61.338 (2)C9—C101.383 (3)
N3—C31.412 (2)C9—H90.9300
N3—H30.86 (2)C10—C111.380 (3)
N4—C61.383 (2)C10—H100.9300
N4—C71.386 (2)C11—C121.376 (3)
N4—H40.83 (2)C11—H110.9300
N5—C41.143 (3)C12—C131.377 (3)
C1—C21.390 (3)C12—H120.9300
C2—C31.405 (3)C13—H130.9300
C2—C41.420 (3)
C1—S1—C5'103.7 (9)S1—C5'—H5'B109.5
C1—S1—C5100.1 (3)H5'A—C5'—H5'B109.5
C1—N1—N2114.01 (17)S1—C5'—H5'C109.5
C1—N1—H1127.0 (17)H5'A—C5'—H5'C109.5
N2—N1—H1119.0 (17)H5'B—C5'—H5'C109.5
C3—N2—N1103.70 (16)N3—C6—N4116.55 (16)
C6—N3—C3123.75 (16)N3—C6—S2124.58 (14)
C6—N3—H3118.7 (14)N4—C6—S2118.86 (14)
C3—N3—H3117.0 (14)O1—C7—N4121.81 (17)
C6—N4—C7128.73 (17)O1—C7—C8122.90 (17)
C6—N4—H4113.2 (14)N4—C7—C8115.28 (16)
C7—N4—H4116.5 (14)C13—C8—C9119.33 (18)
N1—C1—C2105.74 (17)C13—C8—C7117.45 (17)
N1—C1—S1122.02 (15)C9—C8—C7123.21 (17)
C2—C1—S1132.20 (17)C10—C9—C8119.86 (19)
C1—C2—C3104.57 (17)C10—C9—H9120.1
C1—C2—C4125.12 (18)C8—C9—H9120.1
C3—C2—C4130.26 (18)C11—C10—C9120.2 (2)
N2—C3—C2111.98 (16)C11—C10—H10119.9
N2—C3—N3118.36 (17)C9—C10—H10119.9
C2—C3—N3129.60 (17)C12—C11—C10120.1 (2)
N5—C4—C2176.9 (2)C12—C11—H11119.9
S1—C5—H5A109.5C10—C11—H11119.9
S1—C5—H5B109.5C11—C12—C13120.2 (2)
H5A—C5—H5B109.5C11—C12—H12119.9
S1—C5—H5C109.5C13—C12—H12119.9
H5A—C5—H5C109.5C12—C13—C8120.3 (2)
H5B—C5—H5C109.5C12—C13—H13119.9
S1—C5'—H5'A109.5C8—C13—H13119.9
C1—N1—N2—C30.3 (2)C3—N3—C6—N4178.03 (17)
N2—N1—C1—C20.0 (2)C3—N3—C6—S21.5 (3)
N2—N1—C1—S1177.84 (14)C7—N4—C6—N38.7 (3)
C5'—S1—C1—N1133.9 (13)C7—N4—C6—S2170.84 (16)
C5—S1—C1—N1114.3 (5)C6—N4—C7—O12.5 (3)
C5'—S1—C1—C248.9 (13)C6—N4—C7—C8176.96 (18)
C5—S1—C1—C268.5 (6)O1—C7—C8—C1318.2 (3)
N1—C1—C2—C30.3 (2)N4—C7—C8—C13161.26 (18)
S1—C1—C2—C3177.81 (17)O1—C7—C8—C9160.12 (19)
N1—C1—C2—C4177.4 (2)N4—C7—C8—C920.4 (3)
S1—C1—C2—C40.1 (3)C13—C8—C9—C100.0 (3)
N1—N2—C3—C20.5 (2)C7—C8—C9—C10178.28 (18)
N1—N2—C3—N3178.19 (16)C8—C9—C10—C110.1 (3)
C1—C2—C3—N20.5 (2)C9—C10—C11—C120.1 (4)
C4—C2—C3—N2177.0 (2)C10—C11—C12—C130.3 (4)
C1—C2—C3—N3177.90 (19)C11—C12—C13—C80.3 (4)
C4—C2—C3—N30.4 (4)C9—C8—C13—C120.2 (3)
C6—N3—C3—N2127.9 (2)C7—C8—C13—C12178.58 (19)
C6—N3—C3—C254.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O10.86 (2)2.00 (2)2.662 (2)133.9 (18)
N3—H3···O1i0.86 (2)2.46 (2)3.149 (2)137.5 (18)
N4—H4···N5ii0.83 (2)2.40 (2)3.111 (3)143.1 (19)
N1—H1···S2iii0.80 (2)2.54 (2)3.334 (2)170 (2)
C9—H9···N2iv0.932.603.521 (2)169
Symmetry codes: (i) x+1, y, z+1; (ii) x1/2, y+1/2, z1/2; (iii) x+1, y, z; (iv) x1, y, z.
 

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