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In the title compound, C13H12N2OS2, the whole mol­ecule is nearly planar. The mol­ecules are linked by N—H...S hydrogen bonds between the amino group and the thione S atoms, forming molecular chains along the a direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802008231/cv6111sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802008231/cv6111Isup2.hkl
Contains datablock I

CCDC reference: 189385

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.068
  • wR factor = 0.160
  • Data-to-parameter ratio = 10.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 28.35 From the CIF: _reflns_number_total 1819 Count of symmetry unique reflns 1870 Completeness (_total/calc) 97.27% 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 yes WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

S-methyl trans-cis-β-N-(2-hydroxynaphthyl)methylenedithiocarbazate top
Crystal data top
C13H12N2OS2Dx = 1.450 Mg m3
Mr = 276.37Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 4198 reflections
a = 5.1608 (1) Åθ = 2.7–28.3°
b = 9.4909 (2) ŵ = 0.41 mm1
c = 25.8492 (7) ÅT = 293 K
V = 1266.11 (5) Å3Slab, yellow
Z = 40.50 × 0.36 × 0.18 mm
F(000) = 576
Data collection top
Siemens SMART CCD area-detector
diffractometer
1819 independent reflections
Radiation source: fine-focus sealed tube1354 reflections with I > \2s(I)
Graphite monochromatorRint = 0.098
Detector resolution: 8.33 pixels mm-1θmax = 28.4°, θmin = 2.7°
ω scansh = 66
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 129
Tmin = 0.822, Tmax = 0.930l = 2934
7639 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)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0835P)2]
where P = (Fo2 + 2Fc2)/3
1819 reflections(Δ/σ)max < 0.001
168 parametersΔρmax = 1.14 e Å3
0 restraintsΔρmin = 0.66 e Å3
Special details top

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different φ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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
S10.4589 (3)0.10790 (15)0.15175 (5)0.0353 (4)
S20.2867 (3)0.08316 (15)0.04029 (5)0.0399 (4)
O10.9665 (10)0.3408 (5)0.21024 (14)0.0477 (12)
N10.8086 (9)0.3032 (4)0.11433 (14)0.0286 (9)
N20.6577 (9)0.2463 (4)0.07616 (15)0.0346 (11)
H2A0.68180.27280.04470.042*
C11.1388 (11)0.4315 (5)0.1896 (2)0.0345 (13)
C21.2990 (13)0.5013 (7)0.2248 (2)0.0454 (16)
H21.28000.48390.26000.055*
C31.4819 (13)0.5940 (7)0.20861 (19)0.0458 (15)
H31.58740.63840.23280.055*
C41.5143 (11)0.6241 (5)0.1550 (2)0.0321 (11)
C51.7074 (12)0.7214 (6)0.1381 (2)0.0378 (13)
H51.81720.76340.16210.045*
C61.7311 (11)0.7528 (6)0.0873 (2)0.0379 (13)
H61.85450.81790.07650.045*
C71.5688 (12)0.6868 (7)0.0507 (2)0.0439 (15)
H71.58820.70720.01570.053*
C81.3837 (10)0.5933 (6)0.06616 (18)0.0328 (12)
H81.27810.55160.04140.039*
C91.3480 (10)0.5580 (5)0.11881 (19)0.0278 (11)
C101.1568 (10)0.4598 (5)0.13679 (18)0.0265 (11)
C110.9841 (10)0.3911 (5)0.10023 (18)0.0293 (11)
H111.00140.41160.06520.035*
C120.4755 (11)0.1517 (5)0.08604 (17)0.0269 (11)
C130.2061 (12)0.0206 (6)0.1536 (2)0.0445 (15)
H13C0.04190.02500.14870.053*
H13A0.20750.06720.18660.053*
H13B0.23300.08850.12660.053*
H1A0.891 (12)0.310 (6)0.186 (2)0.038 (17)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0478 (8)0.0328 (7)0.0251 (6)0.0078 (7)0.0035 (6)0.0063 (5)
S20.0565 (9)0.0363 (8)0.0268 (6)0.0148 (7)0.0087 (6)0.0006 (6)
O10.063 (3)0.053 (3)0.026 (2)0.023 (2)0.003 (2)0.0027 (19)
N10.039 (2)0.022 (2)0.0245 (19)0.006 (2)0.0022 (18)0.0008 (17)
N20.049 (3)0.033 (2)0.0221 (18)0.009 (2)0.0053 (19)0.0003 (18)
C10.043 (3)0.029 (3)0.032 (2)0.006 (2)0.002 (2)0.003 (2)
C20.065 (4)0.047 (4)0.024 (2)0.014 (3)0.002 (3)0.004 (3)
C30.058 (4)0.045 (4)0.034 (3)0.015 (3)0.004 (3)0.011 (3)
C40.039 (3)0.018 (2)0.040 (3)0.002 (2)0.002 (2)0.006 (2)
C50.041 (3)0.029 (3)0.043 (3)0.003 (3)0.002 (3)0.009 (2)
C60.036 (3)0.028 (3)0.050 (3)0.002 (2)0.006 (3)0.000 (3)
C70.053 (4)0.037 (3)0.041 (3)0.007 (3)0.001 (3)0.006 (3)
C80.042 (3)0.030 (3)0.026 (2)0.006 (3)0.001 (2)0.002 (2)
C90.034 (3)0.020 (2)0.029 (2)0.003 (2)0.001 (2)0.0012 (19)
C100.036 (3)0.017 (2)0.026 (2)0.002 (2)0.000 (2)0.0034 (19)
C110.039 (3)0.024 (2)0.025 (2)0.001 (3)0.001 (2)0.0018 (19)
C120.042 (3)0.015 (2)0.024 (2)0.001 (2)0.000 (2)0.0008 (18)
C130.055 (4)0.035 (3)0.043 (3)0.013 (3)0.002 (3)0.011 (3)
Geometric parameters (Å, º) top
S1—C121.751 (5)C4—C51.427 (7)
S1—C131.786 (6)C5—C61.352 (7)
S2—C121.664 (5)C5—H50.9300
O1—C11.348 (7)C6—C71.411 (8)
O1—H1A0.79 (6)C6—H60.9300
N1—C111.284 (6)C7—C81.363 (8)
N1—N21.368 (5)C7—H70.9300
N2—C121.325 (6)C8—C91.413 (6)
N2—H2A0.8600C8—H80.9300
C1—C101.395 (7)C9—C101.435 (7)
C1—C21.397 (8)C10—C111.453 (7)
C2—C31.356 (8)C11—H110.9300
C2—H20.9300C13—H13C0.9600
C3—C41.424 (7)C13—H13A0.9600
C3—H30.9300C13—H13B0.9600
C4—C91.416 (7)
C12—S1—C13102.9 (3)C8—C7—C6120.6 (5)
C1—O1—H1A104 (4)C8—C7—H7119.7
C11—N1—N2117.0 (4)C6—C7—H7119.7
C12—N2—N1122.2 (4)C7—C8—C9121.8 (5)
C12—N2—H2A118.9C7—C8—H8119.1
N1—N2—H2A118.9C9—C8—H8119.1
O1—C1—C10123.7 (5)C8—C9—C4116.9 (5)
O1—C1—C2115.9 (5)C8—C9—C10123.7 (5)
C10—C1—C2120.5 (5)C4—C9—C10119.3 (4)
C3—C2—C1121.2 (5)C1—C10—C9119.2 (5)
C3—C2—H2119.4C1—C10—C11120.6 (5)
C1—C2—H2119.4C9—C10—C11120.2 (4)
C2—C3—C4120.8 (5)N1—C11—C10122.6 (4)
C2—C3—H3119.6N1—C11—H11118.7
C4—C3—H3119.6C10—C11—H11118.7
C9—C4—C3118.9 (5)N2—C12—S2122.9 (4)
C9—C4—C5120.5 (5)N2—C12—S1112.5 (4)
C3—C4—C5120.6 (5)S2—C12—S1124.6 (3)
C6—C5—C4120.2 (5)S1—C13—H13C109.5
C6—C5—H5119.9S1—C13—H13A109.5
C4—C5—H5119.9H13C—C13—H13A109.5
C5—C6—C7120.0 (5)S1—C13—H13B109.5
C5—C6—H6120.0H13C—C13—H13B109.5
C7—C6—H6120.0H13A—C13—H13B109.5
C11—N1—N2—C12178.2 (5)C5—C4—C9—C10179.5 (5)
O1—C1—C2—C3179.3 (6)O1—C1—C10—C9179.8 (5)
C10—C1—C2—C32.5 (10)C2—C1—C10—C92.1 (8)
C1—C2—C3—C40.7 (10)O1—C1—C10—C110.3 (8)
C2—C3—C4—C91.5 (9)C2—C1—C10—C11177.8 (5)
C2—C3—C4—C5179.8 (6)C8—C9—C10—C1179.5 (5)
C9—C4—C5—C60.8 (8)C4—C9—C10—C10.0 (7)
C3—C4—C5—C6177.9 (6)C8—C9—C10—C110.6 (7)
C4—C5—C6—C71.5 (9)C4—C9—C10—C11179.9 (5)
C5—C6—C7—C81.3 (9)N2—N1—C11—C10179.7 (4)
C6—C7—C8—C90.5 (9)C1—C10—C11—N10.4 (8)
C7—C8—C9—C40.2 (8)C9—C10—C11—N1179.5 (5)
C7—C8—C9—C10179.7 (5)N1—N2—C12—S2179.0 (4)
C3—C4—C9—C8178.7 (5)N1—N2—C12—S11.3 (6)
C5—C4—C9—C80.0 (7)C13—S1—C12—N2179.2 (4)
C3—C4—C9—C101.8 (8)C13—S1—C12—S20.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N10.79 (6)1.90 (5)2.634 (5)153 (6)
C11—H11···S2i0.932.943.780 (5)150
N2—H2A···S2i0.862.643.482 (4)165
C2—H2···S1ii0.932.903.573 (6)130
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x+2, y+1/2, z+1/2.
 

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