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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805034409/ac6214sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805034409/ac6214Isup2.hkl
Contains datablock I

CCDC reference: 289625

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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
C10H13N3SF(000) = 440
Mr = 207.29Dx = 1.302 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3919 reflections
a = 12.225 (3) Åθ = 1.7–26.5°
b = 7.618 (2) ŵ = 0.27 mm1
c = 11.639 (3) ÅT = 298 K
β = 102.660 (4)°Block, colourless
V = 1057.6 (5) Å30.43 × 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 tube2014 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.013
Detector resolution: 83.66 pixels mm-1θmax = 26.5°, θmin = 1.7°
ω scansh = 915
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 97
Tmin = 0.893, Tmax = 0.921l = 1314
5827 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H 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 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.39 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.33274 (3)0.10891 (6)0.46457 (4)0.04602 (18)
N10.29873 (11)0.1679 (2)0.68258 (13)0.0442 (4)
N20.47757 (11)0.1156 (2)0.66750 (13)0.0416 (3)
N30.50346 (11)0.1087 (2)0.78999 (12)0.0425 (4)
C10.11874 (14)0.2585 (3)0.55732 (17)0.0486 (4)
H1A0.15550.32210.50890.058*
C20.00275 (15)0.2530 (3)0.53374 (18)0.0555 (5)
H2A0.03840.31220.46850.067*
C30.05225 (15)0.1610 (3)0.6056 (2)0.0562 (5)
H3B0.13020.15720.58860.067*
C40.00807 (16)0.0751 (3)0.7023 (2)0.0586 (5)
H4A0.02900.01360.75140.070*
C50.12413 (15)0.0796 (3)0.72703 (17)0.0502 (4)
H5A0.16490.02240.79330.060*
C60.17924 (13)0.1689 (2)0.65340 (14)0.0394 (4)
C70.36905 (13)0.1316 (2)0.61183 (14)0.0371 (3)
C80.60570 (14)0.1300 (2)0.84255 (15)0.0382 (4)
C90.70089 (15)0.1677 (3)0.78572 (17)0.0573 (5)
H9A0.67420.17130.70180.086*
H9B0.75650.07730.80580.086*
H9C0.73350.27900.81280.086*
C100.63156 (17)0.1176 (3)0.97342 (16)0.0523 (5)
H10A0.56400.09300.99970.078*
H10B0.66260.22681.00660.078*
H10C0.68470.02500.99830.078*
H1B0.3287 (17)0.162 (3)0.7567 (19)0.049 (5)*
H2B0.5211 (18)0.075 (3)0.6281 (19)0.057 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0381 (3)0.0612 (3)0.0374 (3)0.00241 (17)0.00526 (18)0.00531 (17)
N10.0292 (7)0.0644 (9)0.0379 (7)0.0029 (6)0.0053 (5)0.0052 (7)
N20.0294 (7)0.0587 (9)0.0367 (7)0.0009 (6)0.0068 (6)0.0045 (6)
N30.0336 (7)0.0561 (9)0.0372 (7)0.0009 (6)0.0065 (6)0.0023 (6)
C10.0367 (8)0.0543 (10)0.0542 (10)0.0021 (7)0.0091 (7)0.0065 (8)
C20.0375 (9)0.0634 (12)0.0605 (11)0.0101 (8)0.0005 (8)0.0007 (9)
C30.0310 (8)0.0613 (11)0.0758 (13)0.0005 (8)0.0102 (8)0.0110 (10)
C40.0418 (10)0.0658 (12)0.0742 (13)0.0010 (9)0.0257 (9)0.0009 (10)
C50.0413 (9)0.0629 (11)0.0483 (10)0.0082 (8)0.0142 (7)0.0030 (8)
C60.0291 (7)0.0455 (8)0.0431 (8)0.0025 (6)0.0071 (6)0.0072 (7)
C70.0311 (7)0.0390 (8)0.0408 (8)0.0020 (6)0.0069 (6)0.0021 (6)
C80.0354 (8)0.0378 (8)0.0399 (8)0.0005 (6)0.0049 (6)0.0032 (6)
C90.0389 (9)0.0845 (14)0.0471 (10)0.0165 (9)0.0066 (8)0.0065 (9)
C100.0485 (10)0.0657 (12)0.0404 (9)0.0009 (8)0.0045 (8)0.0027 (8)
Geometric parameters (Å, º) top
S1—C71.6825 (17)C3—H3B0.9300
N1—C71.343 (2)C4—C51.385 (3)
N1—C61.425 (2)C4—H4A0.9300
N1—H1B0.86 (2)C5—C61.380 (3)
N2—C71.348 (2)C5—H5A0.9300
N2—N31.392 (2)C8—C91.487 (2)
N2—H2B0.83 (2)C8—C101.489 (2)
N3—C81.276 (2)C9—H9A0.9600
C1—C61.379 (2)C9—H9B0.9600
C1—C21.385 (2)C9—H9C0.9600
C1—H1A0.9300C10—H10A0.9600
C2—C31.374 (3)C10—H10B0.9600
C2—H2A0.9300C10—H10C0.9600
C3—C41.369 (3)
C7—N1—C6127.96 (14)C1—C6—C5119.98 (15)
C7—N1—H1B114.6 (14)C1—C6—N1122.37 (16)
C6—N1—H1B115.3 (14)C5—C6—N1117.63 (15)
C7—N2—N3118.33 (14)N1—C7—N2114.74 (15)
C7—N2—H2B116.7 (15)N1—C7—S1125.76 (12)
N3—N2—H2B121.3 (15)N2—C7—S1119.50 (12)
C8—N3—N2117.73 (14)N3—C8—C9126.24 (16)
C6—C1—C2119.31 (17)N3—C8—C10116.65 (16)
C6—C1—H1A120.3C9—C8—C10117.11 (15)
C2—C1—H1A120.3C8—C9—H9A109.5
C3—C2—C1120.76 (18)C8—C9—H9B109.5
C3—C2—H2A119.6H9A—C9—H9B109.5
C1—C2—H2A119.6C8—C9—H9C109.5
C4—C3—C2119.77 (17)H9A—C9—H9C109.5
C4—C3—H3B120.1H9B—C9—H9C109.5
C2—C3—H3B120.1C8—C10—H10A109.5
C3—C4—C5120.14 (19)C8—C10—H10B109.5
C3—C4—H4A119.9H10A—C10—H10B109.5
C5—C4—H4A119.9C8—C10—H10C109.5
C6—C5—C4120.01 (18)H10A—C10—H10C109.5
C6—C5—H5A120.0H10B—C10—H10C109.5
C4—C5—H5A120.0
C7—N2—N3—C8165.89 (15)C7—N1—C6—C150.6 (3)
C6—C1—C2—C30.7 (3)C7—N1—C6—C5131.11 (19)
C1—C2—C3—C40.6 (3)C6—N1—C7—N2170.70 (17)
C2—C3—C4—C50.6 (3)C6—N1—C7—S110.3 (3)
C3—C4—C5—C60.8 (3)N3—N2—C7—N110.4 (2)
C2—C1—C6—C52.1 (3)N3—N2—C7—S1170.54 (12)
C2—C1—C6—N1179.62 (17)N2—N3—C8—C92.2 (3)
C4—C5—C6—C12.2 (3)N2—N3—C8—C10178.57 (15)
C4—C5—C6—N1179.47 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···N30.86 (2)2.13 (2)2.581 (2)112
C1—H1A···S10.932.843.248 (2)108
N2—H2B···S1i0.83 (2)2.68 (2)3.4969 (18)168
C9—H9A···S1i0.962.873.546 (2)128
Symmetry code: (i) x+1, y, z+1.
 

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