Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100015390/qa0447sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100015390/qa0447Isup2.hkl |
CCDC reference: 156215
All H atoms were included in the refinement, at calculated positions, as riding models with C—H set to 0.95 Å, except for the amine H atoms, which were located on difference syntheses and both positional and displacement parameters refined.
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.
C7H9N3S | Dx = 1.372 Mg m−3 |
Mr = 167.23 | Melting point: 411-413 K K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.9231 (7) Å | Cell parameters from 6169 reflections |
b = 5.4888 (3) Å | θ = 1.0–27.5° |
c = 12.3788 (8) Å | µ = 0.33 mm−1 |
β = 91.527 (3)° | T = 150 K |
V = 809.82 (8) Å3 | Block, colourless |
Z = 4 | 0.40 × 0.30 × 0.20 mm |
F(000) = 352 |
Enraf Nonius KappaCCD area-detector diffractometer | 1803 independent reflections |
Radiation source: Enraf Nonius FR591 rotating anode | 1483 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 1.7° |
ϕ and ω scans | h = −15→15 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −6→7 |
Tmin = 0.878, Tmax = 0.936 | l = −15→16 |
4691 measured reflections |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.132 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.13 | w = 1/[σ2(Fo2) + (0.0669P)2 + 0.3297P] where P = (Fo2 + 2Fc2)/3 |
1803 reflections | (Δ/σ)max < 0.001 |
116 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
C7H9N3S | V = 809.82 (8) Å3 |
Mr = 167.23 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.9231 (7) Å | µ = 0.33 mm−1 |
b = 5.4888 (3) Å | T = 150 K |
c = 12.3788 (8) Å | 0.40 × 0.30 × 0.20 mm |
β = 91.527 (3)° |
Enraf Nonius KappaCCD area-detector diffractometer | 1803 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | 1483 reflections with I > 2σ(I) |
Tmin = 0.878, Tmax = 0.936 | Rint = 0.037 |
4691 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.132 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.13 | Δρmax = 0.24 e Å−3 |
1803 reflections | Δρmin = −0.32 e Å−3 |
116 parameters |
Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. |
Geometry. Mean plane data ex SHELXL97 ########################### Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 9.0426 (0.0063) x − 2.9114 (0.0038) y − 4.9372 (0.0091) z = 2.5340 (0.0043) * −0.0020 (0.0013) C41 * 0.0020 (0.0013) C42 * 0.0009 (0.0014) C43 * −0.0038 (0.0014) C44 * 0.0039 (0.0015) C45 * −0.0010 (0.0014) C46 Rms deviation of fitted atoms = 0.0026 − 8.1354 (0.0082) x − 3.1653 (0.0026) y + 5.7850 (0.0082) z = 0.0360 (0.0021) Angle to previous plane (with approximate e.s.d.) = 67.56 (0.05) * 0.0082 (0.0006) N4 * −0.0071 (0.0015) C3 * −0.0090 (0.0007) S3 * 0.0268 (0.0013) N2 * −0.0189 (0.0009) N1 Rms deviation of fitted atoms = 0.0160 |
x | y | z | Uiso*/Ueq | ||
N1 | 0.14402 (15) | −0.5007 (3) | −0.06846 (14) | 0.0262 (4) | |
H11 | 0.166 (2) | −0.449 (4) | −0.131 (2) | 0.037 (7)* | |
H12 | 0.087 (2) | −0.612 (5) | −0.077 (2) | 0.044 (7)* | |
N2 | 0.10107 (14) | −0.3002 (3) | −0.01129 (12) | 0.0253 (4) | |
H2 | 0.047 (2) | −0.207 (4) | −0.0406 (18) | 0.032 (6)* | |
C3 | 0.14740 (15) | −0.2346 (3) | 0.08389 (14) | 0.0226 (4) | |
S3 | 0.09915 (5) | 0.01116 (9) | 0.15019 (4) | 0.0322 (2) | |
N4 | 0.22921 (14) | −0.3795 (3) | 0.12235 (12) | 0.0262 (4) | |
H4 | 0.225 (2) | −0.515 (5) | 0.093 (2) | 0.049 (8)* | |
C41 | 0.29000 (15) | −0.3449 (3) | 0.22171 (14) | 0.0223 (4) | |
C42 | 0.36142 (16) | −0.1471 (3) | 0.23506 (15) | 0.0264 (4) | |
H42 | 0.3684 | −0.0311 | 0.1787 | 0.033* | |
C43 | 0.42258 (16) | −0.1195 (4) | 0.33101 (16) | 0.0295 (4) | |
H43 | 0.4716 | 0.0158 | 0.3405 | 0.037* | |
C44 | 0.41248 (17) | −0.2885 (4) | 0.41313 (16) | 0.0305 (5) | |
H44 | 0.4540 | −0.2685 | 0.4791 | 0.038* | |
C45 | 0.34203 (19) | −0.4863 (4) | 0.39914 (17) | 0.0316 (5) | |
H45 | 0.3359 | −0.6033 | 0.4552 | 0.039* | |
C46 | 0.28022 (18) | −0.5144 (3) | 0.30350 (16) | 0.0269 (4) | |
H46 | 0.2313 | −0.6498 | 0.2942 | 0.034* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0322 (10) | 0.0280 (9) | 0.0184 (8) | −0.0009 (7) | 0.0030 (7) | −0.0051 (6) |
N2 | 0.0288 (8) | 0.0279 (8) | 0.0190 (7) | 0.0046 (7) | −0.0031 (6) | −0.0027 (6) |
S3 | 0.0430 (4) | 0.0302 (3) | 0.0229 (3) | 0.0131 (2) | −0.0104 (2) | −0.00705 (18) |
C3 | 0.0271 (9) | 0.0227 (9) | 0.0181 (8) | −0.0026 (7) | 0.0011 (7) | 0.0021 (7) |
N4 | 0.0337 (9) | 0.0233 (8) | 0.0214 (8) | 0.0045 (7) | −0.0044 (6) | −0.0056 (6) |
C41 | 0.0219 (9) | 0.0238 (9) | 0.0209 (9) | 0.0058 (7) | −0.0015 (7) | −0.0021 (7) |
C42 | 0.0279 (10) | 0.0254 (9) | 0.0259 (9) | 0.0012 (8) | 0.0020 (7) | 0.0023 (7) |
C43 | 0.0221 (9) | 0.0300 (10) | 0.0361 (11) | −0.0019 (8) | −0.0018 (8) | −0.0056 (8) |
C44 | 0.0289 (10) | 0.0360 (11) | 0.0261 (10) | 0.0057 (9) | −0.0082 (8) | −0.0044 (8) |
C45 | 0.0384 (12) | 0.0314 (11) | 0.0247 (10) | 0.0033 (9) | −0.0033 (8) | 0.0047 (8) |
C46 | 0.0302 (10) | 0.0229 (9) | 0.0275 (10) | −0.0016 (7) | −0.0015 (8) | 0.0009 (7) |
S3—C3 | 1.6882 (19) | C41—C42 | 1.387 (3) |
N4—C3 | 1.336 (2) | C42—C43 | 1.385 (3) |
N4—C41 | 1.424 (2) | C42—H42 | 0.9500 |
N4—H4 | 0.83 (3) | C43—C44 | 1.384 (3) |
N2—C3 | 1.337 (2) | C43—H43 | 0.9500 |
N2—N1 | 1.412 (2) | C44—C45 | 1.381 (3) |
N2—H2 | 0.89 (2) | C44—H44 | 0.9500 |
N1—H11 | 0.87 (3) | C45—C46 | 1.386 (3) |
N1—H12 | 0.92 (3) | C45—H45 | 0.9500 |
C41—C46 | 1.382 (3) | C46—H46 | 0.9500 |
C3—N4—C41 | 125.37 (16) | C42—C43—C44 | 120.16 (18) |
C3—N4—H4 | 110 (2) | C42—C43—H43 | 119.9 |
C41—N4—H4 | 122 (2) | C44—C43—H43 | 119.9 |
C3—N2—N1 | 120.31 (16) | C45—C44—C43 | 119.96 (17) |
C3—N2—H2 | 118.7 (15) | C45—C44—H44 | 120.0 |
N1—N2—H2 | 120.8 (15) | C43—C44—H44 | 120.0 |
N2—N1—H11 | 108.2 (17) | C44—C45—C46 | 120.16 (18) |
N2—N1—H12 | 107.0 (16) | C44—C45—H45 | 119.9 |
H11—N1—H12 | 111 (2) | C46—C45—H45 | 119.9 |
C46—C41—C42 | 120.21 (17) | C41—C46—C45 | 119.82 (18) |
C46—C41—N4 | 119.50 (17) | C41—C46—H46 | 120.1 |
C42—C41—N4 | 120.26 (16) | C45—C46—H46 | 120.1 |
C43—C42—C41 | 119.68 (17) | N2—C3—N4 | 115.74 (17) |
C43—C42—H42 | 120.2 | N2—C3—S3 | 120.36 (14) |
C41—C42—H42 | 120.2 | N4—C3—S3 | 123.86 (14) |
C3—N4—C41—C46 | 115.1 (2) | C42—C41—C46—C45 | 0.0 (3) |
C3—N4—C41—C42 | −67.0 (3) | N4—C41—C46—C45 | 177.86 (18) |
C46—C41—C42—C43 | −0.3 (3) | C44—C45—C46—C41 | 0.6 (3) |
N4—C41—C42—C43 | −178.13 (16) | N1—N2—C3—N4 | −4.4 (3) |
C41—C42—C43—C44 | 0.0 (3) | N1—N2—C3—S3 | 177.77 (13) |
C42—C43—C44—C45 | 0.5 (3) | C41—N4—C3—N2 | −179.97 (17) |
C43—C44—C45—C46 | −0.8 (3) | C41—N4—C3—S3 | −2.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···N1 | 0.83 (2) | 2.19 (2) | 2.6317 (17) | 113 (2) |
N2—H2···S3i | 0.89 (2) | 2.43 (2) | 3.3097 (17) | 168 (2) |
N1—H11···S3ii | 0.87 (3) | 2.83 (3) | 3.5100 (18) | 137 (2) |
N1—H12···N2iii | 0.92 (3) | 2.56 (3) | 3.296 (2) | 137 (2) |
Symmetry codes: (i) −x, −y, −z; (ii) x, −y−1/2, z−1/2; (iii) −x, −y−1, −z. |
Experimental details
Crystal data | |
Chemical formula | C7H9N3S |
Mr | 167.23 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 150 |
a, b, c (Å) | 11.9231 (7), 5.4888 (3), 12.3788 (8) |
β (°) | 91.527 (3) |
V (Å3) | 809.82 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.33 |
Crystal size (mm) | 0.40 × 0.30 × 0.20 |
Data collection | |
Diffractometer | Enraf Nonius KappaCCD area-detector diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1995) |
Tmin, Tmax | 0.878, 0.936 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4691, 1803, 1483 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.132, 1.13 |
No. of reflections | 1803 |
No. of parameters | 116 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.24, −0.32 |
Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···N1 | 0.83 (2) | 2.19 (2) | 2.6317 (17) | 113 (2) |
N2—H2···S3i | 0.89 (2) | 2.43 (2) | 3.3097 (17) | 168 (2) |
N1—H11···S3ii | 0.87 (3) | 2.83 (3) | 3.5100 (18) | 137 (2) |
N1—H12···N2iii | 0.92 (3) | 2.56 (3) | 3.296 (2) | 137 (2) |
Symmetry codes: (i) −x, −y, −z; (ii) x, −y−1/2, z−1/2; (iii) −x, −y−1, −z. |
Subscribe to Acta Crystallographica Section C: Structural Chemistry
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- Purchase subscription
- Reduced-price subscriptions
- If you have already subscribed, you may need to register
The structure of the title compound, (I), was initially determined using data from visual estimation of photographic intensity measurements at room temperature, with refinement to R = 0.112 (Kolman et al., 1972). However, reported here is a redetermination of the structure using data collected by a modern area detector at 150 K, giving R = 0.040. The previously published value for the dihedral angle between the phenyl ring and the five-membered thiosemicarbazide was 67.5°, which can now be updated to 67.56 (5)°.