1-(2,2-Dimethyl­propion­yl)-3-phenyl­thio­urea

In the title compound, C₁₂H₁₆N₂OS, the mol­ecules adopt a trans–cis 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.

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

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Computing details

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

Crystal data

C12H16N2OS	F(000) = 504
Mr = 236.33	Dx = 1.232 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 697 reflections
a = 10.8783 (18) Å	θ = 1.9–27.0°
b = 6.3632 (11) Å	µ = 0.24 mm^−1
c = 18.963 (3) Å	T = 273 K
β = 103.839 (4)°	Block, colourless
V = 1274.5 (4) Å^3	0.49 × 0.31 × 0.29 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2776 independent reflections
Radiation source: fine-focus sealed tube	2016 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 83.66 pixels mm^-1	θmax = 27.0°, θmin = 1.9°
ω scans	h = −13→12
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −5→8
Tmin = 0.893, Tmax = 0.935	l = −23→24
7283 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.118	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0457P)^2 + 0.3088P] where P = (Fo^2 + 2Fc^2)/3
2776 reflections	(Δ/σ)max < 0.001
148 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.13 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	1.09213 (5)	0.51177 (9)	0.22066 (3)	0.05237 (19)
O1	0.70087 (14)	0.6463 (3)	0.08005 (9)	0.0750 (5)
N1	0.84412 (15)	0.4895 (3)	0.17139 (9)	0.0469 (4)
H1	0.8516	0.3986	0.2057	0.056*
N2	0.94684 (15)	0.7074 (3)	0.10689 (9)	0.0491 (4)
H2	0.8726	0.7309	0.0799	0.059*
C1	0.61634 (19)	0.4175 (4)	0.15769 (12)	0.0517 (5)
C2	0.4901 (2)	0.5158 (5)	0.11844 (15)	0.0768 (8)
H2A	0.4912	0.6634	0.1290	0.115*
H2B	0.4224	0.4499	0.1347	0.115*
H2C	0.4774	0.4956	0.0670	0.115*
C3	0.6174 (2)	0.1846 (4)	0.13752 (15)	0.0717 (7)
H3A	0.6016	0.1709	0.0857	0.107*
H3B	0.5527	0.1118	0.1545	0.107*
H3C	0.6985	0.1251	0.1597	0.107*
C4	0.6354 (2)	0.4411 (5)	0.23990 (13)	0.0719 (7)
H4A	0.7101	0.3661	0.2642	0.108*
H4B	0.5633	0.3849	0.2544	0.108*
H4C	0.6449	0.5872	0.2527	0.108*
C5	0.72261 (19)	0.5295 (3)	0.13257 (12)	0.0489 (5)
C6	0.95670 (18)	0.5767 (3)	0.16239 (11)	0.0427 (5)
C7	1.05236 (18)	0.8123 (3)	0.08896 (10)	0.0446 (5)
C8	1.0782 (2)	1.0162 (4)	0.10980 (12)	0.0554 (5)
H8	1.0298	1.0856	0.1369	0.066*
C9	1.1773 (2)	1.1182 (4)	0.09013 (14)	0.0652 (7)
H9	1.1961	1.2565	0.1046	0.078*
C10	1.2477 (2)	1.0178 (4)	0.04967 (13)	0.0652 (7)
H10	1.3138	1.0876	0.0363	0.078*
C11	1.2203 (2)	0.8136 (5)	0.02887 (13)	0.0690 (7)
H11	1.2682	0.7446	0.0014	0.083*
C12	1.1221 (2)	0.7095 (4)	0.04842 (12)	0.0577 (6)
H12	1.1034	0.5710	0.0342	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0399 (3)	0.0563 (4)	0.0601 (3)	−0.0022 (2)	0.0105 (2)	0.0048 (3)
O1	0.0457 (9)	0.0963 (14)	0.0790 (12)	−0.0084 (9)	0.0072 (8)	0.0352 (11)
N1	0.0377 (9)	0.0518 (10)	0.0519 (10)	−0.0060 (8)	0.0118 (7)	0.0075 (8)
N2	0.0376 (9)	0.0555 (11)	0.0533 (10)	−0.0082 (8)	0.0092 (8)	0.0052 (9)
C1	0.0384 (11)	0.0634 (14)	0.0552 (12)	−0.0067 (10)	0.0150 (9)	−0.0002 (11)
C2	0.0391 (12)	0.103 (2)	0.0886 (18)	−0.0017 (13)	0.0153 (12)	0.0130 (16)
C3	0.0641 (16)	0.0690 (17)	0.0873 (18)	−0.0204 (13)	0.0288 (14)	−0.0059 (13)
C4	0.0561 (14)	0.105 (2)	0.0603 (14)	−0.0026 (14)	0.0259 (12)	−0.0027 (14)
C5	0.0431 (11)	0.0516 (13)	0.0531 (12)	−0.0048 (10)	0.0137 (9)	−0.0011 (10)
C6	0.0414 (11)	0.0399 (11)	0.0475 (11)	−0.0039 (9)	0.0125 (9)	−0.0052 (9)
C7	0.0376 (10)	0.0506 (12)	0.0450 (11)	−0.0050 (9)	0.0086 (9)	0.0053 (9)
C8	0.0536 (13)	0.0514 (13)	0.0633 (13)	−0.0050 (11)	0.0181 (11)	−0.0024 (11)
C9	0.0612 (15)	0.0525 (14)	0.0795 (17)	−0.0136 (12)	0.0119 (13)	0.0093 (12)
C10	0.0433 (12)	0.087 (2)	0.0636 (14)	−0.0124 (13)	0.0106 (11)	0.0245 (14)
C11	0.0508 (14)	0.094 (2)	0.0677 (16)	−0.0012 (14)	0.0260 (12)	−0.0014 (14)
C12	0.0513 (13)	0.0582 (14)	0.0648 (14)	−0.0060 (11)	0.0165 (11)	−0.0078 (11)

Geometric parameters (Å, º)

S1—C6	1.668 (2)	C3—H3B	0.9600
O1—C5	1.220 (2)	C3—H3C	0.9600
N1—C5	1.374 (3)	C4—H4A	0.9600
N1—C6	1.392 (2)	C4—H4B	0.9600
N1—H1	0.8600	C4—H4C	0.9600
N2—C6	1.325 (2)	C7—C8	1.366 (3)
N2—C7	1.437 (2)	C7—C12	1.368 (3)
N2—H2	0.8600	C8—C9	1.384 (3)
C1—C5	1.528 (3)	C8—H8	0.9300
C1—C4	1.530 (3)	C9—C10	1.366 (3)
C1—C2	1.530 (3)	C9—H9	0.9300
C1—C3	1.531 (3)	C10—C11	1.370 (4)
C2—H2A	0.9600	C10—H10	0.9300
C2—H2B	0.9600	C11—C12	1.381 (3)
C2—H2C	0.9600	C11—H11	0.9300
C3—H3A	0.9600	C12—H12	0.9300
C5—N1—C6	128.48 (17)	C1—C4—H4C	109.5
C5—N1—H1	115.8	H4A—C4—H4C	109.5
C6—N1—H1	115.8	H4B—C4—H4C	109.5
C6—N2—C7	124.18 (17)	O1—C5—N1	121.61 (19)
C6—N2—H2	117.9	O1—C5—C1	121.69 (19)
C7—N2—H2	117.9	N1—C5—C1	116.69 (18)
C5—C1—C4	110.08 (18)	N2—C6—N1	116.17 (17)
C5—C1—C2	108.41 (19)	N2—C6—S1	124.91 (15)
C4—C1—C2	110.0 (2)	N1—C6—S1	118.92 (15)
C5—C1—C3	108.80 (18)	C8—C7—C12	120.9 (2)
C4—C1—C3	110.0 (2)	C8—C7—N2	119.56 (19)
C2—C1—C3	109.5 (2)	C12—C7—N2	119.48 (19)
C1—C2—H2A	109.5	C7—C8—C9	119.1 (2)
C1—C2—H2B	109.5	C7—C8—H8	120.4
H2A—C2—H2B	109.5	C9—C8—H8	120.4
C1—C2—H2C	109.5	C10—C9—C8	120.7 (2)
H2A—C2—H2C	109.5	C10—C9—H9	119.7
H2B—C2—H2C	109.5	C8—C9—H9	119.7
C1—C3—H3A	109.5	C9—C10—C11	119.5 (2)
C1—C3—H3B	109.5	C9—C10—H10	120.2
H3A—C3—H3B	109.5	C11—C10—H10	120.2
C1—C3—H3C	109.5	C10—C11—C12	120.4 (2)
H3A—C3—H3C	109.5	C10—C11—H11	119.8
H3B—C3—H3C	109.5	C12—C11—H11	119.8
C1—C4—H4A	109.5	C7—C12—C11	119.3 (2)
C1—C4—H4B	109.5	C7—C12—H12	120.3
H4A—C4—H4B	109.5	C11—C12—H12	120.3
C6—N1—C5—O1	4.2 (3)	C5—N1—C6—S1	176.14 (17)
C6—N1—C5—C1	−176.81 (19)	C6—N2—C7—C8	−99.4 (2)
C4—C1—C5—O1	−132.9 (2)	C6—N2—C7—C12	83.6 (3)
C2—C1—C5—O1	−12.5 (3)	C12—C7—C8—C9	−0.8 (3)
C3—C1—C5—O1	106.5 (3)	N2—C7—C8—C9	−177.79 (19)
C4—C1—C5—N1	48.1 (3)	C7—C8—C9—C10	0.8 (3)
C2—C1—C5—N1	168.5 (2)	C8—C9—C10—C11	−0.5 (4)
C3—C1—C5—N1	−72.5 (2)	C9—C10—C11—C12	0.2 (4)
C7—N2—C6—N1	−179.96 (18)	C8—C7—C12—C11	0.5 (3)
C7—N2—C6—S1	0.0 (3)	N2—C7—C12—C11	177.49 (19)
C5—N1—C6—N2	−3.9 (3)	C10—C11—C12—C7	−0.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.94	2.630 (2)	136
N1—H1···S1^i	0.86	2.82	3.638 (2)	159

Symmetry code: (i) −x+2, y−1/2, −z+1/2.