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In the crystal structure of the title compound, C14H13N3S2, the planar phenyl and thio­phene rings are bridged by a pyrazoline ring. The phenyl group is almost perpendicular to the pyrazoline ring. The pyrazoline ring adopts an envelope conformation, and the two N atoms are involved in an intra­molecular N—H...N(pyrazoline) and an inter­molecular N—H...S hydrogen bond. The average C—N bond length is 1.385 (4) Å. The crystal structure is stabilized by intra- and inter­molecular hydrogen bonds and C—H...π stacking inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806000262/su6262sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806000262/su6262Isup2.hkl
Contains datablock I

CCDC reference: 298549

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C)= 0.003 Å
  • R factor = 0.032
  • wR factor = 0.076
  • Data-to-parameter ratio = 15.1

checkCIF/PLATON results

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Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).

3-Phenyl-5-(2-thienyl)-2-pyrazoline-1-thioamide top
Crystal data top
C14H13N3S2F(000) = 600
Mr = 287.39Dx = 1.406 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 19876 reflections
a = 13.9658 (14) Åθ = 2.5–28.0°
b = 10.7595 (11) ŵ = 0.38 mm1
c = 9.621 (3) ÅT = 296 K
β = 110.128 (13)°Prism, brown
V = 1357.4 (5) Å30.44 × 0.30 × 0.04 mm
Z = 4
Data collection top
Stoe IPDS-2
diffractometer
2659 independent reflections
Radiation source: fine-focus sealed tube2040 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.055
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 2.5°
ω scansh = 1717
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 1313
Tmin = 0.822, Tmax = 0.978l = 1111
18270 measured 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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0403P)2 + 0.0583P]
where P = (Fo2 + 2Fc2)/3
2659 reflections(Δ/σ)max < 0.001
176 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.17 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
C10.26227 (12)0.10667 (15)0.59833 (18)0.0362 (4)
C20.20384 (13)0.16036 (15)0.44937 (18)0.0392 (4)
H2A0.24930.19070.40020.047*
H2B0.15970.22750.45730.047*
C30.14193 (13)0.04857 (15)0.36771 (18)0.0347 (4)
C40.18308 (12)0.00764 (15)0.25561 (17)0.0342 (3)
C50.26955 (13)0.08155 (17)0.2983 (2)0.0439 (4)
H50.30190.10100.39770.053*
C60.30768 (15)0.12629 (18)0.1932 (2)0.0517 (5)
H60.36580.17580.22240.062*
C70.26073 (16)0.09854 (18)0.0461 (2)0.0515 (5)
H70.28700.12910.02370.062*
C80.17464 (15)0.02537 (18)0.0021 (2)0.0483 (4)
H80.14250.00650.09750.058*
C90.13611 (13)0.02004 (16)0.10709 (19)0.0399 (4)
H90.07800.06970.07740.048*
C100.34429 (12)0.16921 (16)0.71126 (19)0.0388 (4)
C110.37485 (14)0.28985 (17)0.7129 (2)0.0475 (4)
H110.34530.34570.63630.057*
C120.45618 (15)0.3209 (2)0.8432 (2)0.0567 (5)
H120.48560.39940.86250.068*
C130.48604 (15)0.2243 (2)0.9358 (2)0.0611 (6)
H130.53890.22821.02640.073*
C140.08723 (12)0.12752 (15)0.49688 (19)0.0366 (4)
N10.15318 (10)0.03720 (13)0.49251 (15)0.0376 (3)
N20.23127 (10)0.00183 (13)0.62148 (15)0.0390 (3)
N30.10471 (12)0.18036 (14)0.62839 (17)0.0485 (4)
H3A0.15540.15630.70360.058*
H3B0.06530.23850.63820.058*
S10.41665 (4)0.09347 (5)0.86956 (6)0.05766 (16)
S20.01135 (3)0.16782 (4)0.34567 (5)0.04663 (14)
H30.0703 (13)0.0680 (14)0.3210 (18)0.028 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0384 (8)0.0385 (9)0.0350 (9)0.0024 (7)0.0169 (7)0.0002 (7)
C20.0486 (9)0.0350 (9)0.0353 (9)0.0007 (7)0.0160 (7)0.0007 (7)
C30.0368 (8)0.0368 (9)0.0307 (8)0.0024 (7)0.0121 (7)0.0036 (7)
C40.0362 (8)0.0339 (8)0.0331 (9)0.0029 (7)0.0126 (7)0.0006 (7)
C50.0443 (9)0.0502 (10)0.0368 (9)0.0085 (8)0.0136 (8)0.0049 (8)
C60.0490 (10)0.0559 (11)0.0546 (12)0.0135 (9)0.0236 (9)0.0023 (9)
C70.0646 (12)0.0531 (11)0.0471 (11)0.0023 (10)0.0324 (9)0.0065 (9)
C80.0617 (11)0.0530 (11)0.0296 (9)0.0014 (9)0.0148 (8)0.0012 (8)
C90.0420 (9)0.0402 (9)0.0351 (9)0.0024 (7)0.0101 (7)0.0004 (7)
C100.0372 (8)0.0452 (10)0.0369 (9)0.0001 (7)0.0163 (7)0.0034 (8)
C110.0474 (10)0.0459 (10)0.0503 (11)0.0015 (8)0.0183 (9)0.0029 (8)
C120.0480 (10)0.0583 (13)0.0653 (14)0.0108 (10)0.0214 (10)0.0169 (11)
C130.0426 (10)0.0830 (16)0.0513 (12)0.0069 (10)0.0081 (9)0.0155 (12)
C140.0424 (9)0.0318 (8)0.0413 (10)0.0029 (7)0.0216 (8)0.0015 (7)
N10.0430 (7)0.0399 (8)0.0308 (7)0.0043 (6)0.0139 (6)0.0013 (6)
N20.0397 (7)0.0444 (8)0.0324 (8)0.0010 (6)0.0119 (6)0.0004 (6)
N30.0615 (9)0.0434 (8)0.0460 (9)0.0079 (7)0.0254 (8)0.0059 (7)
S10.0537 (3)0.0623 (3)0.0460 (3)0.0025 (2)0.0030 (2)0.0060 (2)
S20.0451 (2)0.0462 (3)0.0490 (3)0.0071 (2)0.0168 (2)0.0071 (2)
Geometric parameters (Å, º) top
C1—N21.291 (2)C8—C91.387 (3)
C1—C101.445 (2)C8—H80.9300
C1—C21.500 (2)C9—H90.9300
C2—C31.531 (2)C10—C111.365 (3)
C2—H2A0.9700C10—S11.7163 (18)
C2—H2B0.9700C11—C121.412 (3)
C3—N11.479 (2)C11—H110.9300
C3—C41.512 (2)C12—C131.339 (3)
C3—H30.968 (16)C12—H120.9300
C4—C91.384 (2)C13—S11.703 (2)
C4—C51.385 (2)C13—H130.9300
C5—C61.381 (3)C14—N31.331 (2)
C5—H50.9300C14—N11.349 (2)
C6—C71.372 (3)C14—S21.6797 (18)
C6—H60.9300N1—N21.3937 (19)
C7—C81.376 (3)N3—H3A0.8600
C7—H70.9300N3—H3B0.8600
N2—C1—C10121.17 (15)C7—C8—H8120.2
N2—C1—C2114.13 (14)C9—C8—H8120.2
C10—C1—C2124.68 (15)C4—C9—C8120.75 (16)
C1—C2—C3102.31 (13)C4—C9—H9119.6
C1—C2—H2A111.3C8—C9—H9119.6
C3—C2—H2A111.3C11—C10—C1127.98 (17)
C1—C2—H2B111.3C11—C10—S1110.79 (14)
C3—C2—H2B111.3C1—C10—S1121.22 (13)
H2A—C2—H2B109.2C10—C11—C12112.83 (18)
N1—C3—C4111.67 (13)C10—C11—H11123.6
N1—C3—C2100.96 (13)C12—C11—H11123.6
C4—C3—C2113.21 (13)C13—C12—C11112.24 (19)
N1—C3—H3108.4 (9)C13—C12—H12123.9
C4—C3—H3109.9 (9)C11—C12—H12123.9
C2—C3—H3112.3 (9)C12—C13—S1112.69 (16)
C9—C4—C5119.00 (15)C12—C13—H13123.7
C9—C4—C3119.27 (14)S1—C13—H13123.7
C5—C4—C3121.66 (15)N3—C14—N1115.69 (15)
C6—C5—C4119.97 (17)N3—C14—S2122.73 (13)
C6—C5—H5120.0N1—C14—S2121.58 (13)
C4—C5—H5120.0C14—N1—N2120.15 (13)
C7—C6—C5120.74 (17)C14—N1—C3126.27 (14)
C7—C6—H6119.6N2—N1—C3112.60 (13)
C5—C6—H6119.6C1—N2—N1107.43 (13)
C6—C7—C8119.92 (17)C14—N3—H3A120.0
C6—C7—H7120.0C14—N3—H3B120.0
C8—C7—H7120.0H3A—N3—H3B120.0
C7—C8—C9119.63 (17)C13—S1—C1091.44 (10)
N2—C1—C2—C311.77 (18)C1—C10—C11—C12178.33 (16)
C10—C1—C2—C3170.21 (15)S1—C10—C11—C120.6 (2)
C1—C2—C3—N114.77 (15)C10—C11—C12—C130.7 (2)
C1—C2—C3—C4104.73 (15)C11—C12—C13—S10.4 (2)
N1—C3—C4—C9145.98 (15)N3—C14—N1—N22.1 (2)
C2—C3—C4—C9100.88 (17)S2—C14—N1—N2176.89 (11)
N1—C3—C4—C537.1 (2)N3—C14—N1—C3169.90 (15)
C2—C3—C4—C576.0 (2)S2—C14—N1—C39.1 (2)
C9—C4—C5—C60.1 (3)C4—C3—N1—C1485.92 (19)
C3—C4—C5—C6176.85 (17)C2—C3—N1—C14153.48 (15)
C4—C5—C6—C70.1 (3)C4—C3—N1—N2105.50 (15)
C5—C6—C7—C80.0 (3)C2—C3—N1—N215.09 (17)
C6—C7—C8—C90.1 (3)C10—C1—N2—N1179.31 (14)
C5—C4—C9—C80.1 (3)C2—C1—N2—N12.59 (18)
C3—C4—C9—C8177.06 (16)C14—N1—N2—C1160.82 (15)
C7—C8—C9—C40.2 (3)C3—N1—N2—C18.53 (18)
N2—C1—C10—C11168.88 (17)C12—C13—S1—C100.07 (17)
C2—C1—C10—C119.0 (3)C11—C10—S1—C130.31 (15)
N2—C1—C10—S110.0 (2)C1—C10—S1—C13178.71 (14)
C2—C1—C10—S1172.15 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3B···S2i0.862.763.464 (2)140
N3—H3A···N20.862.262.627 (2)106
Symmetry code: (i) x, y1/2, z+1/2.
 

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