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.
Supporting information
CCDC reference: 239264
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (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
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
top
Crystal data top
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) Å3 | 0.37 × 0.28 × 0.07 mm |
Z = 4 | |
Data collection top
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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.078 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0346P)2 + 0.3514P] where P = (Fo2 + 2Fc2)/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 top
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 F2 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 F2,
conventional R-factors R are based on F, with F
set to zero for negative F2. The observed criterion of F2 >
σ(F2) is used only for calculating -R-factor-obs
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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···H7ix | 2.9863 |
S1···N1i | 3.514 (3) | C2···H1Avi | 3.08 (2) |
S1···H8 | 2.8966 | C3···H6x | 3.0629 |
N1···S1ii | 3.514 (3) | C5···H8vii | 3.0131 |
N1···N2iii | 2.972 (3) | C8···H5viii | 3.0183 |
N1···N3iv | 2.982 (3) | H1A···N3iv | 2.13 (2) |
N2···S1 | 2.578 (2) | H1A···C2iv | 3.08 (2) |
N2···N1iii | 2.972 (3) | H1B···N2iii | 2.12 (2) |
N2···C8v | 3.348 (3) | H1B···C1iii | 3.05 (2) |
N3···N1vi | 2.982 (3) | H4···N3 | 2.7117 |
N3···S1 | 2.562 (2) | H5···H6xi | 2.5564 |
N2···H1Biii | 2.12 (2) | H5···C8vii | 3.0183 |
N2···H8v | 2.9386 | H6···C3xii | 3.0629 |
N3···H4 | 2.7117 | H6···H5xi | 2.5564 |
N3···H1Avi | 2.13 (2) | H7···C1xiii | 2.9863 |
C5···C8vii | 3.462 (3) | H8···S1 | 2.8966 |
C8···C5viii | 3.462 (3) | H8···N2v | 2.9386 |
C8···N2v | 3.348 (3) | H8···C5viii | 3.0131 |
C1···H1Biii | 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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···N3iv | 0.86 (2) | 2.13 (2) | 2.982 (3) | 169.9 (17) |
N1—H1B···N2iii | 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. |