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Crystals of the title compound, C9H10N2S2, were obtained from a condensation reaction of methyl dithio­carbazate and benzaldehyde. The planar dithio­carbazate unit is tilted with respect to the phenyl plane with a dihedral angle of 10.96 (12)°. Inter­molecular N—H...S hydrogen bonding stabilizes the crystal structure. A C—H...π inter­action is also observed in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806010300/sg2015sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806010300/sg2015Isup2.hkl
Contains datablock I

CCDC reference: 605171

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.037
  • wR factor = 0.115
  • Data-to-parameter ratio = 19.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - C8 .. 5.72 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC and Rigaku, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Methyl β-N-phenylmethylene dithiocarbazate top
Crystal data top
C9H10N2S2Z = 2
Mr = 210.31F(000) = 220
Triclinic, P1Dx = 1.339 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.909 (2) ÅCell parameters from 4400 reflections
b = 9.411 (4) Åθ = 3.5–27.0°
c = 10.2423 (18) ŵ = 0.47 mm1
α = 69.929 (11)°T = 295 K
β = 80.34 (2)°Prism, colourless
γ = 78.829 (15)°0.43 × 0.33 × 0.30 mm
V = 521.7 (3) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer
1868 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
Graphite monochromatorθmax = 27.5°, θmin = 3.5°
Detector resolution: 10.00 pixels mm-1h = 76
ω scansk = 1212
5121 measured reflectionsl = 1313
2365 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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0722P)2]
where P = (Fo2 + 2Fc2)/3
2365 reflections(Δ/σ)max = 0.001
119 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.33 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
S10.73857 (9)0.00447 (5)0.64444 (5)0.06479 (19)
S20.88497 (8)0.31891 (5)0.51795 (5)0.05832 (18)
N10.5623 (2)0.36816 (15)0.33482 (14)0.0502 (3)
N20.5797 (3)0.22227 (16)0.42864 (15)0.0558 (4)
H2A0.49650.15900.42400.067*
C10.3636 (3)0.55485 (18)0.15179 (16)0.0459 (4)
C20.5127 (3)0.6610 (2)0.1241 (2)0.0602 (5)
H20.63800.63880.17550.072*
C30.4753 (4)0.7995 (2)0.0204 (3)0.0764 (6)
H30.57780.86950.00090.092*
C40.2905 (4)0.8351 (2)0.0539 (2)0.0787 (6)
H40.26590.92960.12290.094*
C50.1409 (4)0.7322 (3)0.0273 (2)0.0743 (6)
H50.01450.75650.07820.089*
C60.1775 (3)0.5919 (2)0.0754 (2)0.0608 (5)
H60.07560.52190.09300.073*
C70.4007 (3)0.40418 (18)0.25759 (17)0.0497 (4)
H70.30340.33340.26830.060*
C80.7242 (3)0.17826 (18)0.52654 (17)0.0498 (4)
C91.0641 (4)0.2215 (2)0.6564 (2)0.0712 (5)
H9A0.96780.19220.74390.107*
H9B1.16540.28820.65980.107*
H9C1.15500.13180.63980.107*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0804 (4)0.0451 (3)0.0578 (3)0.0150 (2)0.0173 (2)0.0052 (2)
S20.0693 (3)0.0436 (2)0.0609 (3)0.0111 (2)0.0154 (2)0.0098 (2)
N10.0609 (8)0.0371 (6)0.0476 (7)0.0079 (6)0.0096 (6)0.0050 (6)
N20.0667 (9)0.0395 (7)0.0540 (8)0.0137 (6)0.0148 (7)0.0011 (6)
C10.0493 (8)0.0428 (8)0.0439 (8)0.0053 (7)0.0056 (6)0.0122 (6)
C20.0597 (10)0.0448 (9)0.0728 (12)0.0082 (8)0.0187 (9)0.0090 (8)
C30.0786 (13)0.0460 (10)0.0906 (15)0.0130 (9)0.0104 (11)0.0018 (10)
C40.0895 (15)0.0558 (11)0.0641 (12)0.0085 (11)0.0107 (11)0.0052 (9)
C50.0771 (13)0.0787 (14)0.0590 (11)0.0042 (11)0.0258 (10)0.0117 (10)
C60.0629 (10)0.0631 (11)0.0587 (10)0.0108 (9)0.0173 (8)0.0166 (8)
C70.0541 (9)0.0430 (8)0.0508 (9)0.0122 (7)0.0056 (7)0.0111 (7)
C80.0554 (9)0.0414 (8)0.0467 (8)0.0063 (7)0.0012 (7)0.0090 (6)
C90.0735 (12)0.0702 (13)0.0714 (13)0.0052 (10)0.0252 (10)0.0194 (10)
Geometric parameters (Å, º) top
S1—C81.6630 (16)C3—C41.359 (3)
S2—C81.7442 (18)C3—H30.9300
S2—C91.791 (2)C4—C51.365 (4)
N1—C71.263 (2)C4—H40.9300
N1—N21.3755 (18)C5—C61.381 (3)
N2—C81.331 (2)C5—H50.9300
N2—H2A0.8600C6—H60.9300
C1—C61.377 (2)C7—H70.9300
C1—C21.385 (2)C9—H9A0.9600
C1—C71.462 (2)C9—H9B0.9600
C2—C31.375 (3)C9—H9C0.9600
C2—H20.9300
C8—S2—C9102.05 (9)C4—C5—H5120.1
C7—N1—N2115.44 (13)C6—C5—H5120.1
C8—N2—N1120.56 (13)C1—C6—C5120.58 (18)
C8—N2—H2A119.7C1—C6—H6119.7
N1—N2—H2A119.7C5—C6—H6119.7
C6—C1—C2118.75 (16)N1—C7—C1121.41 (14)
C6—C1—C7119.30 (15)N1—C7—H7119.3
C2—C1—C7121.94 (15)C1—C7—H7119.3
C3—C2—C1119.93 (18)N2—C8—S1120.90 (13)
C3—C2—H2120.0N2—C8—S2113.69 (11)
C1—C2—H2120.0S1—C8—S2125.40 (11)
C4—C3—C2120.8 (2)S2—C9—H9A109.5
C4—C3—H3119.6S2—C9—H9B109.5
C2—C3—H3119.6H9A—C9—H9B109.5
C3—C4—C5120.05 (18)S2—C9—H9C109.5
C3—C4—H4120.0H9A—C9—H9C109.5
C5—C4—H4120.0H9B—C9—H9C109.5
C4—C5—C6119.9 (2)
C7—N1—N2—C8171.69 (16)C4—C5—C6—C10.2 (3)
C6—C1—C2—C31.0 (3)N2—N1—C7—C1179.19 (14)
C7—C1—C2—C3177.83 (19)C6—C1—C7—N1176.44 (18)
C1—C2—C3—C41.3 (3)C2—C1—C7—N14.8 (3)
C2—C3—C4—C50.9 (4)N1—N2—C8—S1177.48 (12)
C3—C4—C5—C60.1 (4)N1—N2—C8—S21.7 (2)
C2—C1—C6—C50.2 (3)C9—S2—C8—N2177.92 (14)
C7—C1—C6—C5178.63 (18)C9—S2—C8—S12.97 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···S1i0.862.593.431 (2)168
Symmetry code: (i) x+1, y, z+1.
 

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