Download citation
Download citation
link to html
The two independent mol­ecules of the title compound, C7H6N2S2, are linked by two secondary amino-thione hydrogen bonds [3.344 (3) and 3.376 (3) Å] to form a flat pseudo-centrosymmetric dimer.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803021603/su6049sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803021603/su6049Isup2.hkl
Contains datablock I

CCDC reference: 226934

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.056
  • wR factor = 0.125
  • Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.96
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT420_ALERT_2_C D-H Without Acceptor N2A - H2NA ... ? PLAT420_ALERT_2_C D-H Without Acceptor N2A - H2NB ... ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 5 PLAT731_ALERT_1_C Bond Calc 0.86(3), Rep 0.860(10) ...... 3.00 su-Rat N2A -H2NA 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.86(3), Rep 0.860(10) ...... 3.00 su-Rat N2A -H2NB 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.86(3), Rep 0.860(10) ...... 3.00 su-Rat N2A -H2NB 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.86(3), Rep 0.860(10) ...... 3.00 su-Rat N2A -H2NB 1.555 1.555
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 4 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 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

5-Amino-1,3-benzothiazole-2(3H)-thione top
Crystal data top
C7H6N2S2F(000) = 752
Mr = 182.26Dx = 1.526 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 5.1041 (2) ÅCell parameters from 1662 reflections
b = 20.3859 (7) Åθ = 2.4–23.3°
c = 15.3378 (5) ŵ = 0.60 mm1
β = 96.279 (2)°T = 298 K
V = 1586.4 (1) Å3Block, yellow
Z = 80.32 × 0.12 × 0.09 mm
Data collection top
Bruker APEX area-detector
diffractometer
2332 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.046
Graphite monochromatorθmax = 27.5°, θmin = 1.7°
φ and ω scansh = 56
9371 measured reflectionsk = 2619
3531 independent reflectionsl = 1919
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H atoms treated by a mixture of independent and constrained refinement
S = 0.95 w = 1/[σ2(Fo2) + (0.0557P)2]
where P = (Fo2 + 2Fc2)/3
3531 reflections(Δ/σ)max = 0.001
223 parametersΔρmax = 0.34 e Å3
6 restraintsΔρmin = 0.24 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.4418 (2)0.55768 (4)0.92525 (5)0.0399 (2)
S20.7962 (2)0.64767 (4)0.83740 (5)0.0450 (2)
N10.4257 (5)0.5632 (1)0.7597 (2)0.0383 (6)
N20.2912 (7)0.4066 (2)0.6762 (2)0.0549 (8)
C10.5547 (6)0.5908 (1)0.8317 (2)0.0358 (7)
C20.2217 (6)0.5056 (1)0.8630 (2)0.0352 (7)
C30.0380 (6)0.4608 (1)0.8892 (2)0.0393 (8)
C40.1298 (6)0.4291 (1)0.8267 (2)0.0386 (7)
C50.1176 (6)0.4403 (1)0.7365 (2)0.0397 (8)
C60.0685 (6)0.4836 (1)0.7092 (2)0.0385 (7)
C70.2344 (6)0.5161 (1)0.7733 (2)0.0334 (7)
S1a0.9199 (2)0.67298 (5)0.46636 (5)0.0533 (3)
S2a0.5735 (2)0.57728 (4)0.55131 (6)0.0528 (3)
N1a0.9465 (5)0.6586 (1)0.6311 (2)0.0395 (6)
N2a1.6679 (7)0.8081 (2)0.7304 (3)0.0561 (8)
C1a0.8077 (7)0.6350 (2)0.5578 (2)0.0423 (8)
C2a1.1516 (7)0.7208 (2)0.5322 (2)0.0438 (8)
C3a1.3387 (7)0.7653 (2)0.5095 (2)0.054 (1)
C4a1.5107 (7)0.7929 (2)0.5750 (2)0.0526 (9)
C5a1.4969 (7)0.7779 (2)0.6638 (2)0.0435 (8)
C6a1.3073 (6)0.7341 (1)0.6873 (2)0.0397 (8)
C7a1.1370 (6)0.7059 (1)0.6207 (2)0.0374 (7)
H1n0.467 (6)0.568 (1)0.707 (1)0.04 (1)*
H2n10.418 (4)0.387 (1)0.698 (2)0.05 (1)*
H2n20.306 (7)0.420 (1)0.623 (1)0.05 (1)*
H30.02950.45240.94850.047*
H40.25360.39980.84410.046*
H60.08160.49050.64990.046*
H1na0.904 (5)0.647 (1)0.682 (1)0.03 (1)*
H2na1.809 (4)0.823 (2)0.712 (2)0.07 (1)*
H2nb1.727 (7)0.785 (2)0.775 (2)0.07 (1)*
H3a1.34780.77640.45100.065*
H4a1.63870.82200.56000.063*
H6a1.29500.72390.74590.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0435 (5)0.0425 (4)0.0328 (4)0.0043 (4)0.0012 (4)0.0012 (3)
S20.0427 (5)0.0440 (5)0.0470 (5)0.0072 (4)0.0003 (4)0.0031 (4)
N10.039 (2)0.043 (1)0.033 (2)0.000 (1)0.003 (1)0.002 (1)
N20.051 (2)0.071 (2)0.043 (2)0.024 (2)0.005 (2)0.010 (2)
C10.035 (2)0.034 (2)0.038 (2)0.007 (1)0.000 (1)0.003 (1)
C20.035 (2)0.036 (2)0.036 (2)0.005 (1)0.005 (1)0.001 (1)
C30.043 (2)0.039 (2)0.038 (2)0.002 (2)0.012 (2)0.002 (1)
C40.032 (2)0.039 (2)0.046 (2)0.002 (2)0.008 (2)0.001 (1)
C50.032 (2)0.041 (2)0.046 (2)0.001 (2)0.004 (2)0.008 (1)
C60.037 (2)0.043 (2)0.035 (2)0.002 (2)0.002 (2)0.001 (1)
C70.029 (2)0.033 (2)0.038 (2)0.004 (1)0.004 (1)0.002 (1)
S1a0.0585 (7)0.0674 (6)0.0340 (4)0.0041 (5)0.0051 (4)0.0042 (4)
S2a0.0590 (6)0.0517 (5)0.0447 (5)0.0095 (5)0.0073 (5)0.0023 (4)
N1a0.043 (2)0.042 (2)0.033 (1)0.001 (1)0.002 (1)0.003 (1)
N2a0.042 (2)0.047 (2)0.079 (2)0.007 (2)0.004 (2)0.001 (2)
C1a0.045 (2)0.044 (2)0.038 (2)0.009 (2)0.001 (2)0.000 (1)
C2a0.039 (2)0.050 (2)0.043 (2)0.010 (2)0.008 (2)0.009 (2)
C3a0.056 (2)0.057 (2)0.052 (2)0.010 (2)0.018 (2)0.019 (2)
C4a0.046 (2)0.045 (2)0.069 (2)0.001 (2)0.017 (2)0.015 (2)
C5a0.037 (2)0.035 (2)0.059 (2)0.009 (2)0.005 (2)0.003 (2)
C6a0.041 (2)0.039 (2)0.040 (2)0.004 (2)0.006 (2)0.004 (1)
C7a0.034 (2)0.036 (2)0.043 (2)0.006 (2)0.007 (2)0.004 (1)
Geometric parameters (Å, º) top
S1—C11.740 (3)C2a—C3a1.390 (4)
S1—C21.751 (3)C2a—C7a1.399 (4)
S2—C11.688 (3)C3a—C4a1.380 (5)
N1—C11.344 (4)C4a—C5a1.405 (4)
N1—C71.402 (4)C5a—C6a1.394 (4)
N2—C51.391 (4)C6a—C7a1.391 (4)
C2—C31.400 (4)N1—H1n0.86 (1)
C2—C71.401 (4)N2—H2n10.86 (1)
C3—C41.375 (4)N2—H2n20.85 (1)
C4—C51.409 (4)C3—H30.93
C5—C61.393 (4)C4—H40.93
C6—C71.392 (4)C6—H60.93
S1a—C1a1.753 (3)N1a—H1na0.86 (1)
S1a—C2a1.762 (3)N2a—H2na0.86 (1)
S2a—C1a1.672 (3)N2a—H2nb0.86 (1)
N1a—C1a1.350 (4)C3a—H3a0.93
N1a—C7a1.392 (4)C4a—H4a0.93
N2a—C5a1.410 (4)C6a—H6a0.93
C1—S1—C292.1 (1)C4a—C5a—N2a121.0 (3)
C1—N1—C7116.8 (3)C6a—C5a—N2a118.9 (3)
N1—C1—S1109.8 (2)C5a—C6a—C7a118.0 (3)
N1—C1—S2128.2 (2)C2a—C7a—C6a121.9 (3)
S1—C1—S2122.0 (2)C6a—C7a—N1a126.1 (3)
C3—C2—C7119.1 (3)N1a—C7a—C2a111.9 (3)
C3—C2—S1130.5 (2)C1—N1—H1n125 (2)
C7—C2—S1110.3 (2)C7—N1—H1n118 (2)
C2—C3—C4119.4 (3)C5—N2—H2n1116 (2)
C3—C4—C5121.2 (3)C5—N2—H2n2117 (2)
N2—C5—C4118.6 (3)H2n1—N2—H2n2122 (3)
N2—C5—C6121.2 (3)C4—C3—H3120.3
C4—C5—C6120.2 (3)C2—C3—H3120.3
C5—C6—C7118.1 (3)C3—C4—H4119.4
C2—C7—C6122.1 (3)C5—C4—H4119.4
C2—C7—N1111.0 (3)C7—C6—H6121.0
C6—C7—N1127.0 (3)C5—C6—H6121.0
C1a—S1a—C2a92.5 (2)C1a—N1a—H1na120 (2)
C1a—N1a—C7a117.5 (3)C7a—N1a—H1na123 (2)
N1a—C1a—S1a108.7 (2)C5a—N2a—H2na113 (3)
N1a—C1a—S2a127.4 (2)C5a—N2a—H2nb118 (3)
S1a—C1a—S2a123.9 (2)H2na—N2a—H2nb103 (4)
C3a—C2a—C7a119.7 (3)C4a—C3a—H3a120.6
C3a—C2a—S1a130.8 (3)C2a—C3a—H3a120.6
C7a—C2a—S1a109.4 (2)C3a—C4a—H4a119.2
C2a—C3a—C4a118.9 (3)C5a—C4a—H4a119.2
C3a—C4a—C5a121.5 (3)C7a—C6a—H6a121.0
C4a—C5a—C6a120.0 (3)C5a—C6a—H6a121.0
C7—N1—C1—S2179.1 (2)C7a—N1a—C1a—S2a178.7 (2)
C7—N1—C1—S10.4 (3)C7a—N1a—C1a—S1a0.6 (3)
C2—S1—C1—N10.8 (2)C2a—S1a—C1a—N1a0.6 (2)
C2—S1—C1—S2178.0 (2)C2a—S1a—C1a—S2a178.7 (2)
C1—S1—C2—C3178.0 (3)C1a—S1a—C2a—C3a177.4 (3)
C1—S1—C2—C71.7 (2)C1a—S1a—C2a—C7a0.4 (2)
C7—C2—C3—C41.5 (4)C7a—C2a—C3a—C4a1.5 (5)
S1—C2—C3—C4174.5 (2)S1a—C2a—C3a—C4a175.3 (3)
C2—C3—C4—C50.9 (4)C2a—C3a—C4a—C5a1.4 (5)
C3—C4—C5—N2179.6 (3)C3a—C4a—C5a—C6a0.4 (5)
C3—C4—C5—C60.7 (5)C3a—C4a—C5a—N2a177.8 (3)
N2—C5—C6—C7179.5 (3)C4a—C5a—C6a—C7a0.4 (4)
C4—C5—C6—C71.7 (4)N2a—C5a—C6a—C7a178.7 (3)
C5—C6—C7—C21.1 (4)C5a—C6a—C7a—N1a176.1 (3)
C5—C6—C7—N1177.1 (3)C5a—C6a—C7a—C2a0.3 (5)
C3—C2—C7—C60.4 (4)C1a—N1a—C7a—C6a177.0 (3)
S1—C2—C7—C6176.3 (2)C1a—N1a—C7a—C2a0.3 (4)
C3—C2—C7—N1178.9 (3)C3a—C2a—C7a—C6a0.7 (5)
S1—C2—C7—N12.2 (3)S1a—C2a—C7a—C6a176.7 (2)
C1—N1—C7—C6176.7 (3)C3a—C2a—C7a—N1a177.5 (3)
C1—N1—C7—C21.7 (4)S1a—C2a—C7a—N1a0.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1n···S2a0.86 (1)2.52 (1)3.376 (3)177 (3)
N2—H2n1···N2ai0.86 (1)2.39 (1)3.223 (5)163 (3)
N2—H2n2···S2aii0.85 (1)2.87 (2)3.641 (3)151 (3)
N1a—H1na···S20.86 (1)2.51 (1)3.344 (3)164 (2)
N2a—H2nb···S2iii0.86 (1)2.96 (2)3.685 (3)143 (3)
N2a—H2nb···S1aiv0.86 (1)3.11 (3)3.726 (4)130 (3)
Symmetry codes: (i) x+1, y1/2, z+3/2; (ii) x, y+1, z+1; (iii) x+1, y, z; (iv) x+1, y+3/2, z+1/2.
 

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