2-Amino-5-phenyl-1,3,4-thia­diazo­le at 110 K

The crystal structure of the title compound, C₈H₇N₃S, previously determined at room temperature [Ishankhodzh­aeva, Kadyrova, Surazhskaya, Parpiev & Koz'min (2001). Zh. Org. Khim, 37, 759-761], has been redetermined at 110 K. Comparison of the two structures reveals significant differences in the unit-cell parameters, while the molecular geometry and hydrogen-bonding network are essentially the same in both structures.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.035
• wR factor = 0.078
• Data-to-parameter ratio = 18.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?

   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: COLLECT (Nonius, 1999); cell refinement: EVALCCD (Duisenberg et al., 2003); data reduction: EVALCCD; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); 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).

5-Phenyl-1,3,4-thiadiazol-2-amine

Crystal data

C8H7N3S	F(000) = 368
Mr = 177.24	Dx = 1.427 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 73 reflections
a = 10.604 (5) Å	θ = 6–20°
b = 7.922 (5) Å	µ = 0.33 mm^−1
c = 11.116 (5) Å	T = 100 K
β = 117.965 (5)°	Plate, colorless
V = 824.8 (7) Å^3	0.37 × 0.28 × 0.07 mm
Z = 4

Data collection

Bruker–Nonius KappaCCD diffractometer	2176 independent reflections
Radiation source: fine-focus sealed tube	1699 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
Detector resolution: 9 pixels mm^-1	θmax = 29.0°, θmin = 3.7°
φ and ω–scans (per frame) with 2.0° and 40 sec per frame	h = −14→14
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	k = −10→10
Tmin = 0.887, Tmax = 0.977	l = −15→15
23236 measured 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0346P)^2 + 0.3514P] where P = (Fo^2 + 2Fc^2)/3
2176 reflections	(Δ/σ)max < 0.001
117 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F^{2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F}2, conventional R-factors R are based on F, with F set to zero for negative F^{2. The observed criterion of F}2 > σ(F^{2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F}2 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	0.18079 (4)	−0.10639 (5)	0.44739 (3)	0.0159 (1)
N1	0.04302 (16)	−0.40491 (18)	0.36188 (14)	0.0236 (4)
N2	0.08289 (13)	−0.29552 (16)	0.57333 (12)	0.0175 (3)
N3	0.14372 (13)	−0.15689 (16)	0.65628 (12)	0.0167 (3)
C1	0.09361 (15)	−0.28781 (19)	0.45989 (14)	0.0161 (4)
C2	0.19835 (15)	−0.04771 (19)	0.60647 (14)	0.0148 (4)
C3	0.27254 (15)	0.10710 (19)	0.67702 (15)	0.0163 (4)
C4	0.34781 (16)	0.1101 (2)	0.81950 (15)	0.0208 (4)
C5	0.42189 (18)	0.2539 (2)	0.88646 (17)	0.0249 (5)
C6	0.42129 (17)	0.3961 (2)	0.81354 (17)	0.0250 (5)
C7	0.34557 (17)	0.3948 (2)	0.67228 (17)	0.0245 (5)
C8	0.27197 (16)	0.2513 (2)	0.60402 (16)	0.0203 (4)
H1A	0.064 (2)	−0.396 (2)	0.296 (2)	0.028 (5)*
H1B	0.003 (2)	−0.492 (3)	0.374 (2)	0.037 (6)*
H4	0.34810	0.01550	0.86920	0.0250*
H5	0.47240	0.25500	0.98110	0.0300*
H6	0.47150	0.49200	0.85910	0.0300*
H7	0.34420	0.49050	0.62330	0.0290*
H8	0.22200	0.25080	0.50940	0.0240*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0200 (2)	0.0189 (2)	0.0127 (2)	−0.0038 (2)	0.0109 (1)	−0.0010 (2)
N1	0.0349 (8)	0.0267 (7)	0.0187 (7)	−0.0142 (6)	0.0206 (6)	−0.0087 (6)
N2	0.0239 (6)	0.0196 (6)	0.0143 (6)	−0.0057 (5)	0.0133 (5)	−0.0041 (5)
N3	0.0195 (6)	0.0189 (6)	0.0150 (6)	−0.0029 (5)	0.0108 (5)	−0.0036 (5)
C1	0.0170 (7)	0.0194 (7)	0.0150 (7)	−0.0021 (6)	0.0102 (6)	−0.0002 (6)
C2	0.0162 (7)	0.0192 (7)	0.0116 (6)	0.0009 (6)	0.0088 (6)	−0.0005 (6)
C3	0.0155 (7)	0.0188 (7)	0.0188 (7)	0.0002 (6)	0.0116 (6)	−0.0021 (6)
C4	0.0251 (8)	0.0225 (8)	0.0190 (7)	−0.0012 (6)	0.0138 (6)	−0.0019 (6)
C5	0.0266 (8)	0.0300 (9)	0.0211 (8)	−0.0060 (7)	0.0137 (7)	−0.0103 (7)
C6	0.0253 (8)	0.0227 (8)	0.0336 (9)	−0.0079 (7)	0.0192 (7)	−0.0118 (7)
C7	0.0241 (8)	0.0199 (8)	0.0352 (9)	−0.0009 (6)	0.0186 (7)	0.0012 (7)
C8	0.0195 (8)	0.0221 (8)	0.0211 (7)	0.0004 (6)	0.0110 (6)	0.0011 (6)

Geometric parameters (Å, º)

S1—C1	1.749 (2)	C3—C4	1.400 (2)
S1—C2	1.7518 (18)	C4—C5	1.386 (2)
N1—C1	1.337 (2)	C5—C6	1.386 (2)
N2—N3	1.384 (2)	C6—C7	1.389 (3)
N2—C1	1.320 (2)	C7—C8	1.386 (2)
N3—C2	1.300 (2)	C4—H4	0.9302
N1—H1A	0.86 (2)	C5—H5	0.9302
N1—H1B	0.85 (2)	C6—H6	0.9296
C2—C3	1.470 (2)	C7—H7	0.9295
C3—C8	1.400 (2)	C8—H8	0.9297
S1···N3	2.562 (2)	C1···H7^ix	2.9863
S1···N1^i	3.514 (3)	C2···H1A^vi	3.08 (2)
S1···H8	2.8966	C3···H6^x	3.0629
N1···S1^ii	3.514 (3)	C5···H8^vii	3.0131
N1···N2^iii	2.972 (3)	C8···H5^viii	3.0183
N1···N3^iv	2.982 (3)	H1A···N3^iv	2.13 (2)
N2···S1	2.578 (2)	H1A···C2^iv	3.08 (2)
N2···N1^iii	2.972 (3)	H1B···N2^iii	2.12 (2)
N2···C8^v	3.348 (3)	H1B···C1^iii	3.05 (2)
N3···N1^vi	2.982 (3)	H4···N3	2.7117
N3···S1	2.562 (2)	H5···H6^xi	2.5564
N2···H1B^iii	2.12 (2)	H5···C8^vii	3.0183
N2···H8^v	2.9386	H6···C3^xii	3.0629
N3···H4	2.7117	H6···H5^xi	2.5564
N3···H1A^vi	2.13 (2)	H7···C1^xiii	2.9863
C5···C8^vii	3.462 (3)	H8···S1	2.8966
C8···C5^viii	3.462 (3)	H8···N2^v	2.9386
C8···N2^v	3.348 (3)	H8···C5^viii	3.0131
C1···H1B^iii	3.05 (2)
C1—S1—C2	87.01 (7)	C3—C4—C5	120.03 (15)
N3—N2—C1	112.21 (13)	C4—C5—C6	120.53 (15)
N2—N3—C2	113.94 (12)	C5—C6—C7	119.80 (15)
C1—N1—H1B	118.1 (14)	C6—C7—C8	120.24 (15)
H1A—N1—H1B	123.1 (18)	C3—C8—C7	120.25 (14)
C1—N1—H1A	118.1 (12)	C3—C4—H4	119.97
N1—C1—N2	124.42 (15)	C5—C4—H4	120.01
S1—C1—N2	113.55 (11)	C4—C5—H5	119.73
S1—C1—N1	122.04 (12)	C6—C5—H5	119.74
S1—C2—N3	113.30 (11)	C5—C6—H6	120.08
S1—C2—C3	122.48 (12)	C7—C6—H6	120.12
N3—C2—C3	124.18 (13)	C6—C7—H7	119.89
C2—C3—C4	119.76 (14)	C8—C7—H7	119.87
C2—C3—C8	121.07 (13)	C3—C8—H8	119.84
C4—C3—C8	119.15 (14)	C7—C8—H8	119.91
C1—S1—C2—C3	178.12 (15)	N3—C2—C3—C8	−150.73 (17)
C2—S1—C1—N1	179.50 (15)	S1—C2—C3—C4	−146.99 (14)
C2—S1—C1—N2	−0.13 (13)	C2—C3—C4—C5	177.87 (17)
C1—S1—C2—N3	0.23 (13)	C8—C3—C4—C5	−0.8 (3)
C1—N2—N3—C2	0.2 (2)	C2—C3—C8—C7	−178.37 (17)
N3—N2—C1—N1	−179.61 (16)	C4—C3—C8—C7	0.2 (3)
N3—N2—C1—S1	0.02 (17)	C3—C4—C5—C6	0.6 (3)
N2—N3—C2—S1	−0.27 (18)	C4—C5—C6—C7	0.2 (3)
N2—N3—C2—C3	−178.12 (15)	C5—C6—C7—C8	−0.7 (3)
S1—C2—C3—C8	31.6 (2)	C6—C7—C8—C3	0.5 (3)
N3—C2—C3—C4	30.7 (3)

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x, y−1/2, −z+1/2; (iii) −x, −y−1, −z+1; (iv) x, −y−1/2, z−1/2; (v) −x, −y, −z+1; (vi) x, −y−1/2, z+1/2; (vii) x, −y+1/2, z+1/2; (viii) x, −y+1/2, z−1/2; (ix) x, y−1, z; (x) −x+1, y−1/2, −z+3/2; (xi) −x+1, −y+1, −z+2; (xii) −x+1, y+1/2, −z+3/2; (xiii) x, y+1, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N3^iv	0.86 (2)	2.13 (2)	2.982 (3)	169.9 (17)
N1—H1B···N2^iii	0.85 (2)	2.12 (2)	2.972 (3)	173.9 (18)

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