organic compounds
In the title compound, C10H13N3S, the isopropylidineamine and phenyl groups are trans and cis, respectively, with respect to the thione group across their C-N bonds. The molecule is stablized by intra- and intermolecular hydrogen bonds to form dimers parallel to (010).
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805034409/ac6214sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805034409/ac6214Isup2.hkl |
CCDC reference: 289625
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.043
- wR factor = 0.123
- Data-to-parameter ratio = 16.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C10 PLAT413_ALERT_2_C Short Inter XH3 .. XHn H10A .. H10A .. 2.11 Ang. PLAT748_ALERT_1_C D-H..A Calc 112.5(17), Rep 112.00 ...... Missing su N1 -H1B -N3 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
Acetone 4-phenylthiosemicarbazone top
Crystal data top
C10H13N3S | F(000) = 440 |
Mr = 207.29 | Dx = 1.302 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3919 reflections |
a = 12.225 (3) Å | θ = 1.7–26.5° |
b = 7.618 (2) Å | µ = 0.27 mm−1 |
c = 11.639 (3) Å | T = 298 K |
β = 102.660 (4)° | Block, colourless |
V = 1057.6 (5) Å3 | 0.43 × 0.36 × 0.31 mm |
Z = 4 |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 2187 independent reflections |
Radiation source: fine-focus sealed tube | 2014 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.013 |
Detector resolution: 83.66 pixels mm-1 | θmax = 26.5°, θmin = 1.7° |
ω scans | h = −9→15 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −9→7 |
Tmin = 0.893, Tmax = 0.921 | l = −13→14 |
5827 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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0727P)2 + 0.3195P] where P = (Fo2 + 2Fc2)/3 |
2187 reflections | (Δ/σ)max < 0.001 |
135 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | 0.33274 (3) | 0.10891 (6) | 0.46457 (4) | 0.04602 (18) | |
N1 | 0.29873 (11) | 0.1679 (2) | 0.68258 (13) | 0.0442 (4) | |
N2 | 0.47757 (11) | 0.1156 (2) | 0.66750 (13) | 0.0416 (3) | |
N3 | 0.50346 (11) | 0.1087 (2) | 0.78999 (12) | 0.0425 (4) | |
C1 | 0.11874 (14) | 0.2585 (3) | 0.55732 (17) | 0.0486 (4) | |
H1A | 0.1555 | 0.3221 | 0.5089 | 0.058* | |
C2 | 0.00275 (15) | 0.2530 (3) | 0.53374 (18) | 0.0555 (5) | |
H2A | −0.0384 | 0.3122 | 0.4685 | 0.067* | |
C3 | −0.05225 (15) | 0.1610 (3) | 0.6056 (2) | 0.0562 (5) | |
H3B | −0.1302 | 0.1572 | 0.5886 | 0.067* | |
C4 | 0.00807 (16) | 0.0751 (3) | 0.7023 (2) | 0.0586 (5) | |
H4A | −0.0290 | 0.0136 | 0.7514 | 0.070* | |
C5 | 0.12413 (15) | 0.0796 (3) | 0.72703 (17) | 0.0502 (4) | |
H5A | 0.1649 | 0.0224 | 0.7933 | 0.060* | |
C6 | 0.17924 (13) | 0.1689 (2) | 0.65340 (14) | 0.0394 (4) | |
C7 | 0.36905 (13) | 0.1316 (2) | 0.61183 (14) | 0.0371 (3) | |
C8 | 0.60570 (14) | 0.1300 (2) | 0.84255 (15) | 0.0382 (4) | |
C9 | 0.70089 (15) | 0.1677 (3) | 0.78572 (17) | 0.0573 (5) | |
H9A | 0.6742 | 0.1713 | 0.7018 | 0.086* | |
H9B | 0.7565 | 0.0773 | 0.8058 | 0.086* | |
H9C | 0.7335 | 0.2790 | 0.8128 | 0.086* | |
C10 | 0.63156 (17) | 0.1176 (3) | 0.97342 (16) | 0.0523 (5) | |
H10A | 0.5640 | 0.0930 | 0.9997 | 0.078* | |
H10B | 0.6626 | 0.2268 | 1.0066 | 0.078* | |
H10C | 0.6847 | 0.0250 | 0.9983 | 0.078* | |
H1B | 0.3287 (17) | 0.162 (3) | 0.7567 (19) | 0.049 (5)* | |
H2B | 0.5211 (18) | 0.075 (3) | 0.6281 (19) | 0.057 (6)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0381 (3) | 0.0612 (3) | 0.0374 (3) | 0.00241 (17) | 0.00526 (18) | −0.00531 (17) |
N1 | 0.0292 (7) | 0.0644 (9) | 0.0379 (7) | 0.0029 (6) | 0.0053 (5) | −0.0052 (7) |
N2 | 0.0294 (7) | 0.0587 (9) | 0.0367 (7) | 0.0009 (6) | 0.0068 (6) | −0.0045 (6) |
N3 | 0.0336 (7) | 0.0561 (9) | 0.0372 (7) | 0.0009 (6) | 0.0065 (6) | −0.0023 (6) |
C1 | 0.0367 (8) | 0.0543 (10) | 0.0542 (10) | 0.0021 (7) | 0.0091 (7) | 0.0065 (8) |
C2 | 0.0375 (9) | 0.0634 (12) | 0.0605 (11) | 0.0101 (8) | −0.0005 (8) | 0.0007 (9) |
C3 | 0.0310 (8) | 0.0613 (11) | 0.0758 (13) | −0.0005 (8) | 0.0102 (8) | −0.0110 (10) |
C4 | 0.0418 (10) | 0.0658 (12) | 0.0742 (13) | −0.0010 (9) | 0.0257 (9) | 0.0009 (10) |
C5 | 0.0413 (9) | 0.0629 (11) | 0.0483 (10) | 0.0082 (8) | 0.0142 (7) | 0.0030 (8) |
C6 | 0.0291 (7) | 0.0455 (8) | 0.0431 (8) | 0.0025 (6) | 0.0071 (6) | −0.0072 (7) |
C7 | 0.0311 (7) | 0.0390 (8) | 0.0408 (8) | −0.0020 (6) | 0.0069 (6) | −0.0021 (6) |
C8 | 0.0354 (8) | 0.0378 (8) | 0.0399 (8) | 0.0005 (6) | 0.0049 (6) | −0.0032 (6) |
C9 | 0.0389 (9) | 0.0845 (14) | 0.0471 (10) | −0.0165 (9) | 0.0066 (8) | −0.0065 (9) |
C10 | 0.0485 (10) | 0.0657 (12) | 0.0404 (9) | −0.0009 (8) | 0.0045 (8) | −0.0027 (8) |
Geometric parameters (Å, º) top
S1—C7 | 1.6825 (17) | C3—H3B | 0.9300 |
N1—C7 | 1.343 (2) | C4—C5 | 1.385 (3) |
N1—C6 | 1.425 (2) | C4—H4A | 0.9300 |
N1—H1B | 0.86 (2) | C5—C6 | 1.380 (3) |
N2—C7 | 1.348 (2) | C5—H5A | 0.9300 |
N2—N3 | 1.392 (2) | C8—C9 | 1.487 (2) |
N2—H2B | 0.83 (2) | C8—C10 | 1.489 (2) |
N3—C8 | 1.276 (2) | C9—H9A | 0.9600 |
C1—C6 | 1.379 (2) | C9—H9B | 0.9600 |
C1—C2 | 1.385 (2) | C9—H9C | 0.9600 |
C1—H1A | 0.9300 | C10—H10A | 0.9600 |
C2—C3 | 1.374 (3) | C10—H10B | 0.9600 |
C2—H2A | 0.9300 | C10—H10C | 0.9600 |
C3—C4 | 1.369 (3) | ||
C7—N1—C6 | 127.96 (14) | C1—C6—C5 | 119.98 (15) |
C7—N1—H1B | 114.6 (14) | C1—C6—N1 | 122.37 (16) |
C6—N1—H1B | 115.3 (14) | C5—C6—N1 | 117.63 (15) |
C7—N2—N3 | 118.33 (14) | N1—C7—N2 | 114.74 (15) |
C7—N2—H2B | 116.7 (15) | N1—C7—S1 | 125.76 (12) |
N3—N2—H2B | 121.3 (15) | N2—C7—S1 | 119.50 (12) |
C8—N3—N2 | 117.73 (14) | N3—C8—C9 | 126.24 (16) |
C6—C1—C2 | 119.31 (17) | N3—C8—C10 | 116.65 (16) |
C6—C1—H1A | 120.3 | C9—C8—C10 | 117.11 (15) |
C2—C1—H1A | 120.3 | C8—C9—H9A | 109.5 |
C3—C2—C1 | 120.76 (18) | C8—C9—H9B | 109.5 |
C3—C2—H2A | 119.6 | H9A—C9—H9B | 109.5 |
C1—C2—H2A | 119.6 | C8—C9—H9C | 109.5 |
C4—C3—C2 | 119.77 (17) | H9A—C9—H9C | 109.5 |
C4—C3—H3B | 120.1 | H9B—C9—H9C | 109.5 |
C2—C3—H3B | 120.1 | C8—C10—H10A | 109.5 |
C3—C4—C5 | 120.14 (19) | C8—C10—H10B | 109.5 |
C3—C4—H4A | 119.9 | H10A—C10—H10B | 109.5 |
C5—C4—H4A | 119.9 | C8—C10—H10C | 109.5 |
C6—C5—C4 | 120.01 (18) | H10A—C10—H10C | 109.5 |
C6—C5—H5A | 120.0 | H10B—C10—H10C | 109.5 |
C4—C5—H5A | 120.0 | ||
C7—N2—N3—C8 | −165.89 (15) | C7—N1—C6—C1 | −50.6 (3) |
C6—C1—C2—C3 | 0.7 (3) | C7—N1—C6—C5 | 131.11 (19) |
C1—C2—C3—C4 | 0.6 (3) | C6—N1—C7—N2 | −170.70 (17) |
C2—C3—C4—C5 | −0.6 (3) | C6—N1—C7—S1 | 10.3 (3) |
C3—C4—C5—C6 | −0.8 (3) | N3—N2—C7—N1 | 10.4 (2) |
C2—C1—C6—C5 | −2.1 (3) | N3—N2—C7—S1 | −170.54 (12) |
C2—C1—C6—N1 | 179.62 (17) | N2—N3—C8—C9 | 2.2 (3) |
C4—C5—C6—C1 | 2.2 (3) | N2—N3—C8—C10 | −178.57 (15) |
C4—C5—C6—N1 | −179.47 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···N3 | 0.86 (2) | 2.13 (2) | 2.581 (2) | 112 |
C1—H1A···S1 | 0.93 | 2.84 | 3.248 (2) | 108 |
N2—H2B···S1i | 0.83 (2) | 2.68 (2) | 3.4969 (18) | 168 |
C9—H9A···S1i | 0.96 | 2.87 | 3.546 (2) | 128 |
Symmetry code: (i) −x+1, −y, −z+1. |