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In the title compound, C12H16N2OS, the mol­ecules adopt a transcis configuration of the 2,2-dimethyl­propionyl and phenyl groups relative to the S atom across the C—N bonds. The mol­ecules are linked by N—H...S inter­actions, forming one-dimensional zigzag chains along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046551/sa2022sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046551/sa2022Isup2.hkl
Contains datablock I

CCDC reference: 630447

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.047
  • wR factor = 0.118
  • Data-to-parameter ratio = 18.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1
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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

1-(2,2-Dimethylpropionyl)-3-phenylthiourea top
Crystal data top
C12H16N2OSF(000) = 504
Mr = 236.33Dx = 1.232 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 697 reflections
a = 10.8783 (18) Åθ = 1.9–27.0°
b = 6.3632 (11) ŵ = 0.24 mm1
c = 18.963 (3) ÅT = 273 K
β = 103.839 (4)°Block, colourless
V = 1274.5 (4) Å30.49 × 0.31 × 0.29 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2776 independent reflections
Radiation source: fine-focus sealed tube2016 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
Detector resolution: 83.66 pixels mm-1θmax = 27.0°, θmin = 1.9°
ω scansh = 1312
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 58
Tmin = 0.893, Tmax = 0.935l = 2324
7283 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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0457P)2 + 0.3088P]
where P = (Fo2 + 2Fc2)/3
2776 reflections(Δ/σ)max < 0.001
148 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.13 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they ar 1058 e defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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
xyzUiso*/Ueq
S11.09213 (5)0.51177 (9)0.22066 (3)0.05237 (19)
O10.70087 (14)0.6463 (3)0.08005 (9)0.0750 (5)
N10.84412 (15)0.4895 (3)0.17139 (9)0.0469 (4)
H10.85160.39860.20570.056*
N20.94684 (15)0.7074 (3)0.10689 (9)0.0491 (4)
H20.87260.73090.07990.059*
C10.61634 (19)0.4175 (4)0.15769 (12)0.0517 (5)
C20.4901 (2)0.5158 (5)0.11844 (15)0.0768 (8)
H2A0.49120.66340.12900.115*
H2B0.42240.44990.13470.115*
H2C0.47740.49560.06700.115*
C30.6174 (2)0.1846 (4)0.13752 (15)0.0717 (7)
H3A0.60160.17090.08570.107*
H3B0.55270.11180.15450.107*
H3C0.69850.12510.15970.107*
C40.6354 (2)0.4411 (5)0.23990 (13)0.0719 (7)
H4A0.71010.36610.26420.108*
H4B0.56330.38490.25440.108*
H4C0.64490.58720.25270.108*
C50.72261 (19)0.5295 (3)0.13257 (12)0.0489 (5)
C60.95670 (18)0.5767 (3)0.16239 (11)0.0427 (5)
C71.05236 (18)0.8123 (3)0.08896 (10)0.0446 (5)
C81.0782 (2)1.0162 (4)0.10980 (12)0.0554 (5)
H81.02981.08560.13690.066*
C91.1773 (2)1.1182 (4)0.09013 (14)0.0652 (7)
H91.19611.25650.10460.078*
C101.2477 (2)1.0178 (4)0.04967 (13)0.0652 (7)
H101.31381.08760.03630.078*
C111.2203 (2)0.8136 (5)0.02887 (13)0.0690 (7)
H111.26820.74460.00140.083*
C121.1221 (2)0.7095 (4)0.04842 (12)0.0577 (6)
H121.10340.57100.03420.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0399 (3)0.0563 (4)0.0601 (3)0.0022 (2)0.0105 (2)0.0048 (3)
O10.0457 (9)0.0963 (14)0.0790 (12)0.0084 (9)0.0072 (8)0.0352 (11)
N10.0377 (9)0.0518 (10)0.0519 (10)0.0060 (8)0.0118 (7)0.0075 (8)
N20.0376 (9)0.0555 (11)0.0533 (10)0.0082 (8)0.0092 (8)0.0052 (9)
C10.0384 (11)0.0634 (14)0.0552 (12)0.0067 (10)0.0150 (9)0.0002 (11)
C20.0391 (12)0.103 (2)0.0886 (18)0.0017 (13)0.0153 (12)0.0130 (16)
C30.0641 (16)0.0690 (17)0.0873 (18)0.0204 (13)0.0288 (14)0.0059 (13)
C40.0561 (14)0.105 (2)0.0603 (14)0.0026 (14)0.0259 (12)0.0027 (14)
C50.0431 (11)0.0516 (13)0.0531 (12)0.0048 (10)0.0137 (9)0.0011 (10)
C60.0414 (11)0.0399 (11)0.0475 (11)0.0039 (9)0.0125 (9)0.0052 (9)
C70.0376 (10)0.0506 (12)0.0450 (11)0.0050 (9)0.0086 (9)0.0053 (9)
C80.0536 (13)0.0514 (13)0.0633 (13)0.0050 (11)0.0181 (11)0.0024 (11)
C90.0612 (15)0.0525 (14)0.0795 (17)0.0136 (12)0.0119 (13)0.0093 (12)
C100.0433 (12)0.087 (2)0.0636 (14)0.0124 (13)0.0106 (11)0.0245 (14)
C110.0508 (14)0.094 (2)0.0677 (16)0.0012 (14)0.0260 (12)0.0014 (14)
C120.0513 (13)0.0582 (14)0.0648 (14)0.0060 (11)0.0165 (11)0.0078 (11)
Geometric parameters (Å, º) top
S1—C61.668 (2)C3—H3B0.9600
O1—C51.220 (2)C3—H3C0.9600
N1—C51.374 (3)C4—H4A0.9600
N1—C61.392 (2)C4—H4B0.9600
N1—H10.8600C4—H4C0.9600
N2—C61.325 (2)C7—C81.366 (3)
N2—C71.437 (2)C7—C121.368 (3)
N2—H20.8600C8—C91.384 (3)
C1—C51.528 (3)C8—H80.9300
C1—C41.530 (3)C9—C101.366 (3)
C1—C21.530 (3)C9—H90.9300
C1—C31.531 (3)C10—C111.370 (4)
C2—H2A0.9600C10—H100.9300
C2—H2B0.9600C11—C121.381 (3)
C2—H2C0.9600C11—H110.9300
C3—H3A0.9600C12—H120.9300
C5—N1—C6128.48 (17)C1—C4—H4C109.5
C5—N1—H1115.8H4A—C4—H4C109.5
C6—N1—H1115.8H4B—C4—H4C109.5
C6—N2—C7124.18 (17)O1—C5—N1121.61 (19)
C6—N2—H2117.9O1—C5—C1121.69 (19)
C7—N2—H2117.9N1—C5—C1116.69 (18)
C5—C1—C4110.08 (18)N2—C6—N1116.17 (17)
C5—C1—C2108.41 (19)N2—C6—S1124.91 (15)
C4—C1—C2110.0 (2)N1—C6—S1118.92 (15)
C5—C1—C3108.80 (18)C8—C7—C12120.9 (2)
C4—C1—C3110.0 (2)C8—C7—N2119.56 (19)
C2—C1—C3109.5 (2)C12—C7—N2119.48 (19)
C1—C2—H2A109.5C7—C8—C9119.1 (2)
C1—C2—H2B109.5C7—C8—H8120.4
H2A—C2—H2B109.5C9—C8—H8120.4
C1—C2—H2C109.5C10—C9—C8120.7 (2)
H2A—C2—H2C109.5C10—C9—H9119.7
H2B—C2—H2C109.5C8—C9—H9119.7
C1—C3—H3A109.5C9—C10—C11119.5 (2)
C1—C3—H3B109.5C9—C10—H10120.2
H3A—C3—H3B109.5C11—C10—H10120.2
C1—C3—H3C109.5C10—C11—C12120.4 (2)
H3A—C3—H3C109.5C10—C11—H11119.8
H3B—C3—H3C109.5C12—C11—H11119.8
C1—C4—H4A109.5C7—C12—C11119.3 (2)
C1—C4—H4B109.5C7—C12—H12120.3
H4A—C4—H4B109.5C11—C12—H12120.3
C6—N1—C5—O14.2 (3)C5—N1—C6—S1176.14 (17)
C6—N1—C5—C1176.81 (19)C6—N2—C7—C899.4 (2)
C4—C1—C5—O1132.9 (2)C6—N2—C7—C1283.6 (3)
C2—C1—C5—O112.5 (3)C12—C7—C8—C90.8 (3)
C3—C1—C5—O1106.5 (3)N2—C7—C8—C9177.79 (19)
C4—C1—C5—N148.1 (3)C7—C8—C9—C100.8 (3)
C2—C1—C5—N1168.5 (2)C8—C9—C10—C110.5 (4)
C3—C1—C5—N172.5 (2)C9—C10—C11—C120.2 (4)
C7—N2—C6—N1179.96 (18)C8—C7—C12—C110.5 (3)
C7—N2—C6—S10.0 (3)N2—C7—C12—C11177.49 (19)
C5—N1—C6—N23.9 (3)C10—C11—C12—C70.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O10.861.942.630 (2)136
N1—H1···S1i0.862.823.638 (2)159
Symmetry code: (i) x+2, y1/2, z+1/2.
 

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