Methyl β-N-phenyl­methyl­enedithio­carbazate

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.

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

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Computing details

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

Crystal data

C9H10N2S2	Z = 2
Mr = 210.31	F(000) = 220
Triclinic, P1	Dx = 1.339 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.909 (2) Å	Cell parameters from 4400 reflections
b = 9.411 (4) Å	θ = 3.5–27.0°
c = 10.2423 (18) Å	µ = 0.47 mm^−1
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) Å^3

Data collection

Rigaku R-AXIS RAPID diffractometer	1868 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 27.5°, θmin = 3.5°
Detector resolution: 10.00 pixels mm^-1	h = −7→6
ω scans	k = −12→12
5121 measured reflections	l = −13→13
2365 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0722P)^2] where P = (Fo^2 + 2Fc^2)/3
2365 reflections	(Δ/σ)max = 0.001
119 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.73857 (9)	0.00447 (5)	0.64444 (5)	0.06479 (19)
S2	0.88497 (8)	0.31891 (5)	0.51795 (5)	0.05832 (18)
N1	0.5623 (2)	0.36816 (15)	0.33482 (14)	0.0502 (3)
N2	0.5797 (3)	0.22227 (16)	0.42864 (15)	0.0558 (4)
H2A	0.4965	0.1590	0.4240	0.067*
C1	0.3636 (3)	0.55485 (18)	0.15179 (16)	0.0459 (4)
C2	0.5127 (3)	0.6610 (2)	0.1241 (2)	0.0602 (5)
H2	0.6380	0.6388	0.1755	0.072*
C3	0.4753 (4)	0.7995 (2)	0.0204 (3)	0.0764 (6)
H3	0.5778	0.8695	0.0009	0.092*
C4	0.2905 (4)	0.8351 (2)	−0.0539 (2)	0.0787 (6)
H4	0.2659	0.9296	−0.1229	0.094*
C5	0.1409 (4)	0.7322 (3)	−0.0273 (2)	0.0743 (6)
H5	0.0145	0.7565	−0.0782	0.089*
C6	0.1775 (3)	0.5919 (2)	0.0754 (2)	0.0608 (5)
H6	0.0756	0.5219	0.0930	0.073*
C7	0.4007 (3)	0.40418 (18)	0.25759 (17)	0.0497 (4)
H7	0.3034	0.3334	0.2683	0.060*
C8	0.7242 (3)	0.17826 (18)	0.52654 (17)	0.0498 (4)
C9	1.0641 (4)	0.2215 (2)	0.6564 (2)	0.0712 (5)
H9A	0.9678	0.1922	0.7439	0.107*
H9B	1.1654	0.2882	0.6598	0.107*
H9C	1.1550	0.1318	0.6398	0.107*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0804 (4)	0.0451 (3)	0.0578 (3)	−0.0150 (2)	−0.0173 (2)	0.0052 (2)
S2	0.0693 (3)	0.0436 (2)	0.0609 (3)	−0.0111 (2)	−0.0154 (2)	−0.0098 (2)
N1	0.0609 (8)	0.0371 (6)	0.0476 (7)	−0.0079 (6)	−0.0096 (6)	−0.0050 (6)
N2	0.0667 (9)	0.0395 (7)	0.0540 (8)	−0.0137 (6)	−0.0148 (7)	0.0011 (6)
C1	0.0493 (8)	0.0428 (8)	0.0439 (8)	−0.0053 (7)	−0.0056 (6)	−0.0122 (6)
C2	0.0597 (10)	0.0448 (9)	0.0728 (12)	−0.0082 (8)	−0.0187 (9)	−0.0090 (8)
C3	0.0786 (13)	0.0460 (10)	0.0906 (15)	−0.0130 (9)	−0.0104 (11)	−0.0018 (10)
C4	0.0895 (15)	0.0558 (11)	0.0641 (12)	0.0085 (11)	−0.0107 (11)	0.0052 (9)
C5	0.0771 (13)	0.0787 (14)	0.0590 (11)	0.0042 (11)	−0.0258 (10)	−0.0117 (10)
C6	0.0629 (10)	0.0631 (11)	0.0587 (10)	−0.0108 (9)	−0.0173 (8)	−0.0166 (8)
C7	0.0541 (9)	0.0430 (8)	0.0508 (9)	−0.0122 (7)	−0.0056 (7)	−0.0111 (7)
C8	0.0554 (9)	0.0414 (8)	0.0467 (8)	−0.0063 (7)	−0.0012 (7)	−0.0090 (6)
C9	0.0735 (12)	0.0702 (13)	0.0714 (13)	−0.0052 (10)	−0.0252 (10)	−0.0194 (10)

Geometric parameters (Å, º)

S1—C8	1.6630 (16)	C3—C4	1.359 (3)
S2—C8	1.7442 (18)	C3—H3	0.9300
S2—C9	1.791 (2)	C4—C5	1.365 (4)
N1—C7	1.263 (2)	C4—H4	0.9300
N1—N2	1.3755 (18)	C5—C6	1.381 (3)
N2—C8	1.331 (2)	C5—H5	0.9300
N2—H2A	0.8600	C6—H6	0.9300
C1—C6	1.377 (2)	C7—H7	0.9300
C1—C2	1.385 (2)	C9—H9A	0.9600
C1—C7	1.462 (2)	C9—H9B	0.9600
C2—C3	1.375 (3)	C9—H9C	0.9600
C2—H2	0.9300
C8—S2—C9	102.05 (9)	C4—C5—H5	120.1
C7—N1—N2	115.44 (13)	C6—C5—H5	120.1
C8—N2—N1	120.56 (13)	C1—C6—C5	120.58 (18)
C8—N2—H2A	119.7	C1—C6—H6	119.7
N1—N2—H2A	119.7	C5—C6—H6	119.7
C6—C1—C2	118.75 (16)	N1—C7—C1	121.41 (14)
C6—C1—C7	119.30 (15)	N1—C7—H7	119.3
C2—C1—C7	121.94 (15)	C1—C7—H7	119.3
C3—C2—C1	119.93 (18)	N2—C8—S1	120.90 (13)
C3—C2—H2	120.0	N2—C8—S2	113.69 (11)
C1—C2—H2	120.0	S1—C8—S2	125.40 (11)
C4—C3—C2	120.8 (2)	S2—C9—H9A	109.5
C4—C3—H3	119.6	S2—C9—H9B	109.5
C2—C3—H3	119.6	H9A—C9—H9B	109.5
C3—C4—C5	120.05 (18)	S2—C9—H9C	109.5
C3—C4—H4	120.0	H9A—C9—H9C	109.5
C5—C4—H4	120.0	H9B—C9—H9C	109.5
C4—C5—C6	119.9 (2)
C7—N1—N2—C8	−171.69 (16)	C4—C5—C6—C1	0.2 (3)
C6—C1—C2—C3	−1.0 (3)	N2—N1—C7—C1	−179.19 (14)
C7—C1—C2—C3	177.83 (19)	C6—C1—C7—N1	−176.44 (18)
C1—C2—C3—C4	1.3 (3)	C2—C1—C7—N1	4.8 (3)
C2—C3—C4—C5	−0.9 (4)	N1—N2—C8—S1	177.48 (12)
C3—C4—C5—C6	0.1 (4)	N1—N2—C8—S2	−1.7 (2)
C2—C1—C6—C5	0.2 (3)	C9—S2—C8—N2	−177.92 (14)
C7—C1—C6—C5	−178.63 (18)	C9—S2—C8—S1	2.97 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···S1^i	0.86	2.59	3.431 (2)	168

Symmetry code: (i) −x+1, −y, −z+1.