5-Amino-1,3-benzo­thia­zole-2(3H)-thione

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.

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

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

Crystal data

C7H6N2S2	F(000) = 752
Mr = 182.26	Dx = 1.526 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.1041 (2) Å	Cell parameters from 1662 reflections
b = 20.3859 (7) Å	θ = 2.4–23.3°
c = 15.3378 (5) Å	µ = 0.60 mm^−1
β = 96.279 (2)°	T = 298 K
V = 1586.4 (1) Å^3	Block, yellow
Z = 8	0.32 × 0.12 × 0.09 mm

Data collection

Bruker APEX area-detector diffractometer	2332 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.046
Graphite monochromator	θmax = 27.5°, θmin = 1.7°
φ and ω scans	h = −5→6
9371 measured reflections	k = −26→19
3531 independent reflections	l = −19→19

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ^2(Fo^2) + (0.0557P)^2] where P = (Fo^2 + 2Fc^2)/3
3531 reflections	(Δ/σ)max = 0.001
223 parameters	Δρmax = 0.34 e Å^−3
6 restraints	Δρmin = −0.24 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.4418 (2)	0.55768 (4)	0.92525 (5)	0.0399 (2)
S2	0.7962 (2)	0.64767 (4)	0.83740 (5)	0.0450 (2)
N1	0.4257 (5)	0.5632 (1)	0.7597 (2)	0.0383 (6)
N2	−0.2912 (7)	0.4066 (2)	0.6762 (2)	0.0549 (8)
C1	0.5547 (6)	0.5908 (1)	0.8317 (2)	0.0358 (7)
C2	0.2217 (6)	0.5056 (1)	0.8630 (2)	0.0352 (7)
C3	0.0380 (6)	0.4608 (1)	0.8892 (2)	0.0393 (8)
C4	−0.1298 (6)	0.4291 (1)	0.8267 (2)	0.0386 (7)
C5	−0.1176 (6)	0.4403 (1)	0.7365 (2)	0.0397 (8)
C6	0.0685 (6)	0.4836 (1)	0.7092 (2)	0.0385 (7)
C7	0.2344 (6)	0.5161 (1)	0.7733 (2)	0.0334 (7)
S1a	0.9199 (2)	0.67298 (5)	0.46636 (5)	0.0533 (3)
S2a	0.5735 (2)	0.57728 (4)	0.55131 (6)	0.0528 (3)
N1a	0.9465 (5)	0.6586 (1)	0.6311 (2)	0.0395 (6)
N2a	1.6679 (7)	0.8081 (2)	0.7304 (3)	0.0561 (8)
C1a	0.8077 (7)	0.6350 (2)	0.5578 (2)	0.0423 (8)
C2a	1.1516 (7)	0.7208 (2)	0.5322 (2)	0.0438 (8)
C3a	1.3387 (7)	0.7653 (2)	0.5095 (2)	0.054 (1)
C4a	1.5107 (7)	0.7929 (2)	0.5750 (2)	0.0526 (9)
C5a	1.4969 (7)	0.7779 (2)	0.6638 (2)	0.0435 (8)
C6a	1.3073 (6)	0.7341 (1)	0.6873 (2)	0.0397 (8)
C7a	1.1370 (6)	0.7059 (1)	0.6207 (2)	0.0374 (7)
H1n	0.467 (6)	0.568 (1)	0.707 (1)	0.04 (1)*
H2n1	−0.418 (4)	0.387 (1)	0.698 (2)	0.05 (1)*
H2n2	−0.306 (7)	0.420 (1)	0.623 (1)	0.05 (1)*
H3	0.0295	0.4524	0.9485	0.047*
H4	−0.2536	0.3998	0.8441	0.046*
H6	0.0816	0.4905	0.6499	0.046*
H1na	0.904 (5)	0.647 (1)	0.682 (1)	0.03 (1)*
H2na	1.809 (4)	0.823 (2)	0.712 (2)	0.07 (1)*
H2nb	1.727 (7)	0.785 (2)	0.775 (2)	0.07 (1)*
H3a	1.3478	0.7764	0.4510	0.065*
H4a	1.6387	0.8220	0.5600	0.063*
H6a	1.2950	0.7239	0.7459	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0435 (5)	0.0425 (4)	0.0328 (4)	−0.0043 (4)	0.0012 (4)	0.0012 (3)
S2	0.0427 (5)	0.0440 (5)	0.0470 (5)	−0.0072 (4)	−0.0003 (4)	0.0031 (4)
N1	0.039 (2)	0.043 (1)	0.033 (2)	0.000 (1)	0.003 (1)	0.002 (1)
N2	0.051 (2)	0.071 (2)	0.043 (2)	−0.024 (2)	0.005 (2)	−0.010 (2)
C1	0.035 (2)	0.034 (2)	0.038 (2)	0.007 (1)	0.000 (1)	0.003 (1)
C2	0.035 (2)	0.036 (2)	0.036 (2)	0.005 (1)	0.005 (1)	0.001 (1)
C3	0.043 (2)	0.039 (2)	0.038 (2)	0.002 (2)	0.012 (2)	0.002 (1)
C4	0.032 (2)	0.039 (2)	0.046 (2)	−0.002 (2)	0.008 (2)	−0.001 (1)
C5	0.032 (2)	0.041 (2)	0.046 (2)	0.001 (2)	0.004 (2)	−0.008 (1)
C6	0.037 (2)	0.043 (2)	0.035 (2)	0.002 (2)	0.002 (2)	−0.001 (1)
C7	0.029 (2)	0.033 (2)	0.038 (2)	0.004 (1)	0.004 (1)	0.002 (1)
S1a	0.0585 (7)	0.0674 (6)	0.0340 (4)	0.0041 (5)	0.0051 (4)	0.0042 (4)
S2a	0.0590 (6)	0.0517 (5)	0.0447 (5)	−0.0095 (5)	−0.0073 (5)	−0.0023 (4)
N1a	0.043 (2)	0.042 (2)	0.033 (1)	−0.001 (1)	0.002 (1)	0.003 (1)
N2a	0.042 (2)	0.047 (2)	0.079 (2)	−0.007 (2)	0.004 (2)	0.001 (2)
C1a	0.045 (2)	0.044 (2)	0.038 (2)	0.009 (2)	0.001 (2)	0.000 (1)
C2a	0.039 (2)	0.050 (2)	0.043 (2)	0.010 (2)	0.008 (2)	0.009 (2)
C3a	0.056 (2)	0.057 (2)	0.052 (2)	0.010 (2)	0.018 (2)	0.019 (2)
C4a	0.046 (2)	0.045 (2)	0.069 (2)	0.001 (2)	0.017 (2)	0.015 (2)
C5a	0.037 (2)	0.035 (2)	0.059 (2)	0.009 (2)	0.005 (2)	0.003 (2)
C6a	0.041 (2)	0.039 (2)	0.040 (2)	0.004 (2)	0.006 (2)	0.004 (1)
C7a	0.034 (2)	0.036 (2)	0.043 (2)	0.006 (2)	0.007 (2)	0.004 (1)

Geometric parameters (Å, º)

S1—C1	1.740 (3)	C2a—C3a	1.390 (4)
S1—C2	1.751 (3)	C2a—C7a	1.399 (4)
S2—C1	1.688 (3)	C3a—C4a	1.380 (5)
N1—C1	1.344 (4)	C4a—C5a	1.405 (4)
N1—C7	1.402 (4)	C5a—C6a	1.394 (4)
N2—C5	1.391 (4)	C6a—C7a	1.391 (4)
C2—C3	1.400 (4)	N1—H1n	0.86 (1)
C2—C7	1.401 (4)	N2—H2n1	0.86 (1)
C3—C4	1.375 (4)	N2—H2n2	0.85 (1)
C4—C5	1.409 (4)	C3—H3	0.93
C5—C6	1.393 (4)	C4—H4	0.93
C6—C7	1.392 (4)	C6—H6	0.93
S1a—C1a	1.753 (3)	N1a—H1na	0.86 (1)
S1a—C2a	1.762 (3)	N2a—H2na	0.86 (1)
S2a—C1a	1.672 (3)	N2a—H2nb	0.86 (1)
N1a—C1a	1.350 (4)	C3a—H3a	0.93
N1a—C7a	1.392 (4)	C4a—H4a	0.93
N2a—C5a	1.410 (4)	C6a—H6a	0.93
C1—S1—C2	92.1 (1)	C4a—C5a—N2a	121.0 (3)
C1—N1—C7	116.8 (3)	C6a—C5a—N2a	118.9 (3)
N1—C1—S1	109.8 (2)	C5a—C6a—C7a	118.0 (3)
N1—C1—S2	128.2 (2)	C2a—C7a—C6a	121.9 (3)
S1—C1—S2	122.0 (2)	C6a—C7a—N1a	126.1 (3)
C3—C2—C7	119.1 (3)	N1a—C7a—C2a	111.9 (3)
C3—C2—S1	130.5 (2)	C1—N1—H1n	125 (2)
C7—C2—S1	110.3 (2)	C7—N1—H1n	118 (2)
C2—C3—C4	119.4 (3)	C5—N2—H2n1	116 (2)
C3—C4—C5	121.2 (3)	C5—N2—H2n2	117 (2)
N2—C5—C4	118.6 (3)	H2n1—N2—H2n2	122 (3)
N2—C5—C6	121.2 (3)	C4—C3—H3	120.3
C4—C5—C6	120.2 (3)	C2—C3—H3	120.3
C5—C6—C7	118.1 (3)	C3—C4—H4	119.4
C2—C7—C6	122.1 (3)	C5—C4—H4	119.4
C2—C7—N1	111.0 (3)	C7—C6—H6	121.0
C6—C7—N1	127.0 (3)	C5—C6—H6	121.0
C1a—S1a—C2a	92.5 (2)	C1a—N1a—H1na	120 (2)
C1a—N1a—C7a	117.5 (3)	C7a—N1a—H1na	123 (2)
N1a—C1a—S1a	108.7 (2)	C5a—N2a—H2na	113 (3)
N1a—C1a—S2a	127.4 (2)	C5a—N2a—H2nb	118 (3)
S1a—C1a—S2a	123.9 (2)	H2na—N2a—H2nb	103 (4)
C3a—C2a—C7a	119.7 (3)	C4a—C3a—H3a	120.6
C3a—C2a—S1a	130.8 (3)	C2a—C3a—H3a	120.6
C7a—C2a—S1a	109.4 (2)	C3a—C4a—H4a	119.2
C2a—C3a—C4a	118.9 (3)	C5a—C4a—H4a	119.2
C3a—C4a—C5a	121.5 (3)	C7a—C6a—H6a	121.0
C4a—C5a—C6a	120.0 (3)	C5a—C6a—H6a	121.0
C7—N1—C1—S2	179.1 (2)	C7a—N1a—C1a—S2a	178.7 (2)
C7—N1—C1—S1	0.4 (3)	C7a—N1a—C1a—S1a	0.6 (3)
C2—S1—C1—N1	0.8 (2)	C2a—S1a—C1a—N1a	−0.6 (2)
C2—S1—C1—S2	−178.0 (2)	C2a—S1a—C1a—S2a	−178.7 (2)
C1—S1—C2—C3	−178.0 (3)	C1a—S1a—C2a—C3a	177.4 (3)
C1—S1—C2—C7	−1.7 (2)	C1a—S1a—C2a—C7a	0.4 (2)
C7—C2—C3—C4	−1.5 (4)	C7a—C2a—C3a—C4a	1.5 (5)
S1—C2—C3—C4	174.5 (2)	S1a—C2a—C3a—C4a	−175.3 (3)
C2—C3—C4—C5	0.9 (4)	C2a—C3a—C4a—C5a	−1.4 (5)
C3—C4—C5—N2	179.6 (3)	C3a—C4a—C5a—C6a	0.4 (5)
C3—C4—C5—C6	0.7 (5)	C3a—C4a—C5a—N2a	−177.8 (3)
N2—C5—C6—C7	179.5 (3)	C4a—C5a—C6a—C7a	0.4 (4)
C4—C5—C6—C7	−1.7 (4)	N2a—C5a—C6a—C7a	178.7 (3)
C5—C6—C7—C2	1.1 (4)	C5a—C6a—C7a—N1a	176.1 (3)
C5—C6—C7—N1	−177.1 (3)	C5a—C6a—C7a—C2a	−0.3 (5)
C3—C2—C7—C6	0.4 (4)	C1a—N1a—C7a—C6a	−177.0 (3)
S1—C2—C7—C6	−176.3 (2)	C1a—N1a—C7a—C2a	−0.3 (4)
C3—C2—C7—N1	178.9 (3)	C3a—C2a—C7a—C6a	−0.7 (5)
S1—C2—C7—N1	2.2 (3)	S1a—C2a—C7a—C6a	176.7 (2)
C1—N1—C7—C6	176.7 (3)	C3a—C2a—C7a—N1a	−177.5 (3)
C1—N1—C7—C2	−1.7 (4)	S1a—C2a—C7a—N1a	−0.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···S2a	0.86 (1)	2.52 (1)	3.376 (3)	177 (3)
N2—H2n1···N2a^i	0.86 (1)	2.39 (1)	3.223 (5)	163 (3)
N2—H2n2···S2a^ii	0.85 (1)	2.87 (2)	3.641 (3)	151 (3)
N1a—H1na···S2	0.86 (1)	2.51 (1)	3.344 (3)	164 (2)
N2a—H2nb···S2^iii	0.86 (1)	2.96 (2)	3.685 (3)	143 (3)
N2a—H2nb···S1a^iv	0.86 (1)	3.11 (3)	3.726 (4)	130 (3)

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x, −y+1, −z+1; (iii) x+1, y, z; (iv) x+1, −y+3/2, z+1/2.