N-Benzoyl-N'-(2,6-di­methyl­phenyl)­thio­urea

In the title compound, C₁₆H₁₆N₂OS, the benzoyl and di­methyl­phenyl substituents have trans and cis configurations, respectively, with respect to the thio­urea S atom. The aromatic rings of the two substituents are nearly perpendicular to each other. The mol­ecules are interconnected into molecular chains along the b direction.

Key indicators

• Single-crystal X-ray study
• T = 213 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.053
• wR factor = 0.148
• Data-to-parameter ratio = 16.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_420  Alert C D-H Without Acceptor       N(2)   -   H(2A)             ?


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); 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, 1990).

N-benzoyl-N'-(2,6-dimethylphenyl)thiourea

Crystal data

C16H16N2OS	F(000) = 600
Mr = 284.37	Dx = 1.286 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.5077 (3) Å	Cell parameters from 5482 reflections
b = 11.1226 (4) Å	θ = 2.8–28.3°
c = 14.0147 (5) Å	µ = 0.22 mm^−1
β = 97.823 (1)°	T = 213 K
V = 1468.27 (9) Å^3	Slab, colorless
Z = 4	0.40 × 0.28 × 0.12 mm

Data collection

Siemens SMART CCD area-detector diffractometer	3564 independent reflections
Radiation source: fine-focus sealed tube	2416 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.084
Detector resolution: 8.33 pixels mm^-1	θmax = 28.3°, θmin = 2.8°
ω scans	h = −11→12
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	k = −14→14
Tmin = 0.918, Tmax = 0.974	l = −18→12
8741 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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ^2(Fo^2) + (0.0672P)^2] where P = (Fo^2 + 2Fc^2)/3
3564 reflections	(Δ/σ)max = 0.001
219 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.52 e Å^−3

Special details

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different φ angle (0, 88 and 180°) for the crystal and each exposure of 30 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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 are 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	0.53550 (6)	0.41236 (5)	0.61939 (4)	0.03153 (18)
O1	0.79071 (17)	0.26662 (15)	0.39239 (12)	0.0408 (4)
N1	0.58617 (18)	0.23315 (16)	0.50274 (13)	0.0267 (4)
N2	0.72130 (18)	0.40448 (17)	0.49622 (13)	0.0266 (4)
C1	0.8636 (2)	0.5862 (2)	0.39470 (17)	0.0347 (5)
C2	0.9492 (3)	0.6680 (3)	0.35361 (19)	0.0432 (6)
C3	1.0561 (2)	0.6275 (3)	0.30486 (19)	0.0457 (7)
C4	1.0780 (3)	0.5047 (3)	0.29584 (19)	0.0465 (7)
C5	0.9943 (2)	0.4221 (2)	0.33629 (17)	0.0372 (5)
C6	0.8857 (2)	0.4633 (2)	0.38622 (14)	0.0271 (4)
C7	0.7966 (2)	0.3688 (2)	0.42417 (14)	0.0260 (4)
C8	0.6153 (2)	0.34353 (18)	0.53638 (14)	0.0236 (4)
C9	0.4653 (2)	0.16526 (18)	0.52329 (14)	0.0255 (4)
C10	0.3468 (2)	0.1639 (2)	0.45239 (16)	0.0311 (5)
C11	0.2304 (3)	0.0965 (2)	0.47058 (19)	0.0390 (6)
C12	0.2336 (3)	0.0310 (2)	0.55480 (19)	0.0424 (6)
H12A	0.1552	−0.0147	0.5653	0.051*
C13	0.3525 (3)	0.0333 (2)	0.62316 (18)	0.0371 (5)
C14	0.4718 (2)	0.10102 (19)	0.60898 (15)	0.0298 (5)
C15	0.6005 (2)	0.1039 (2)	0.68421 (17)	0.0390 (5)
H15A	0.6847	0.1063	0.6533	0.058*
H15B	0.6021	0.0332	0.7236	0.058*
H15C	0.5971	0.1741	0.7237	0.058*
C16	0.3467 (3)	0.2320 (2)	0.35928 (18)	0.0434 (6)
H16A	0.2561	0.2229	0.3204	0.065*
H16B	0.4198	0.2008	0.3252	0.065*
H16C	0.3642	0.3157	0.3730	0.065*
H1A	0.635 (2)	0.209 (2)	0.4628 (16)	0.026 (6)*
H1	0.788 (3)	0.628 (2)	0.4272 (18)	0.048 (7)*
H3	1.116 (3)	0.695 (2)	0.2757 (18)	0.047 (7)*
H11	0.152 (3)	0.101 (2)	0.425 (2)	0.046 (7)*
H2A	0.738 (3)	0.469 (2)	0.5161 (19)	0.037 (7)*
H13	0.360 (2)	−0.016 (2)	0.682 (2)	0.047 (7)*
H2	0.932 (3)	0.753 (3)	0.3671 (19)	0.056 (8)*
H4	1.151 (3)	0.473 (2)	0.263 (2)	0.050 (8)*
H5	1.003 (3)	0.329 (3)	0.3311 (19)	0.054 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0373 (3)	0.0318 (3)	0.0295 (3)	0.0009 (2)	0.0188 (2)	−0.0043 (2)
O1	0.0487 (10)	0.0349 (9)	0.0449 (10)	−0.0076 (7)	0.0287 (8)	−0.0108 (7)
N1	0.0312 (9)	0.0264 (9)	0.0260 (9)	−0.0037 (7)	0.0168 (7)	−0.0037 (7)
N2	0.0308 (9)	0.0240 (10)	0.0274 (9)	−0.0050 (7)	0.0130 (7)	−0.0044 (7)
C1	0.0268 (11)	0.0408 (14)	0.0377 (13)	0.0005 (10)	0.0090 (9)	0.0094 (10)
C2	0.0348 (12)	0.0418 (15)	0.0527 (16)	−0.0022 (11)	0.0053 (11)	0.0194 (12)
C3	0.0305 (12)	0.0617 (18)	0.0451 (15)	−0.0104 (12)	0.0065 (10)	0.0221 (13)
C4	0.0351 (13)	0.068 (2)	0.0404 (14)	−0.0121 (12)	0.0194 (11)	−0.0013 (13)
C5	0.0355 (12)	0.0466 (15)	0.0329 (12)	−0.0093 (10)	0.0171 (10)	−0.0086 (10)
C6	0.0237 (9)	0.0369 (12)	0.0212 (10)	−0.0045 (9)	0.0050 (7)	0.0010 (8)
C7	0.0247 (10)	0.0325 (12)	0.0223 (10)	0.0006 (9)	0.0088 (7)	−0.0014 (8)
C8	0.0250 (9)	0.0258 (11)	0.0210 (10)	0.0007 (8)	0.0072 (7)	0.0010 (7)
C9	0.0300 (10)	0.0223 (10)	0.0272 (11)	−0.0026 (8)	0.0143 (8)	−0.0029 (8)
C10	0.0354 (11)	0.0286 (12)	0.0311 (11)	−0.0014 (9)	0.0106 (9)	−0.0031 (8)
C11	0.0335 (12)	0.0397 (14)	0.0441 (14)	−0.0038 (10)	0.0069 (10)	−0.0033 (11)
C12	0.0379 (13)	0.0406 (15)	0.0535 (16)	−0.0095 (11)	0.0236 (11)	−0.0028 (11)
C13	0.0449 (13)	0.0351 (13)	0.0360 (13)	−0.0031 (10)	0.0227 (11)	0.0040 (10)
C14	0.0354 (11)	0.0274 (11)	0.0296 (11)	−0.0002 (9)	0.0148 (9)	−0.0010 (8)
C15	0.0446 (13)	0.0443 (14)	0.0297 (12)	−0.0010 (11)	0.0109 (10)	0.0059 (10)
C16	0.0499 (14)	0.0433 (15)	0.0359 (13)	−0.0046 (12)	0.0022 (11)	0.0058 (11)

Geometric parameters (Å, º)

S1—C8	1.6599 (19)	C6—C7	1.494 (3)
O1—C7	1.219 (3)	C9—C14	1.392 (3)
N1—C8	1.331 (3)	C9—C10	1.397 (3)
N1—C9	1.436 (2)	C10—C11	1.389 (3)
N1—H1A	0.82 (2)	C10—C16	1.509 (3)
N2—C7	1.373 (2)	C11—C12	1.384 (4)
N2—C8	1.395 (2)	C11—H11	0.92 (3)
N2—H2A	0.78 (3)	C12—C13	1.379 (3)
C1—C6	1.390 (3)	C12—H12A	0.9300
C1—C2	1.396 (3)	C13—C14	1.398 (3)
C1—H1	1.01 (3)	C13—H13	0.98 (3)
C2—C3	1.375 (4)	C14—C15	1.503 (3)
C2—H2	0.98 (3)	C15—H15A	0.9600
C3—C4	1.390 (4)	C15—H15B	0.9600
C3—H3	1.06 (3)	C15—H15C	0.9600
C4—C5	1.386 (3)	C16—H16A	0.9600
C4—H4	0.95 (3)	C16—H16B	0.9600
C5—C6	1.401 (3)	C16—H16C	0.9600
C5—H5	1.05 (3)
C8—N1—C9	123.20 (17)	C14—C9—C10	123.00 (19)
C8—N1—H1A	115.5 (16)	C14—C9—N1	120.03 (19)
C9—N1—H1A	120.7 (16)	C10—C9—N1	116.92 (18)
C7—N2—C8	129.31 (19)	C11—C10—C9	117.4 (2)
C7—N2—H2A	115.4 (19)	C11—C10—C16	121.6 (2)
C8—N2—H2A	115.2 (19)	C9—C10—C16	120.99 (19)
C6—C1—C2	120.1 (2)	C12—C11—C10	121.0 (2)
C6—C1—H1	127.9 (15)	C12—C11—H11	123.3 (16)
C2—C1—H1	112.0 (15)	C10—C11—H11	115.6 (16)
C3—C2—C1	120.2 (3)	C13—C12—C11	120.2 (2)
C3—C2—H2	124.3 (16)	C13—C12—H12A	119.9
C1—C2—H2	115.3 (17)	C11—C12—H12A	119.9
C2—C3—C4	119.8 (2)	C12—C13—C14	121.1 (2)
C2—C3—H3	115.7 (15)	C12—C13—H13	121.9 (14)
C4—C3—H3	124.4 (15)	C14—C13—H13	116.9 (14)
C5—C4—C3	120.8 (2)	C9—C14—C13	117.2 (2)
C5—C4—H4	116.8 (17)	C9—C14—C15	122.03 (19)
C3—C4—H4	122.4 (17)	C13—C14—C15	120.7 (2)
C4—C5—C6	119.4 (2)	C14—C15—H15A	109.5
C4—C5—H5	125.1 (14)	C14—C15—H15B	109.5
C6—C5—H5	115.4 (14)	H15A—C15—H15B	109.5
C1—C6—C5	119.6 (2)	C14—C15—H15C	109.5
C1—C6—C7	124.19 (18)	H15A—C15—H15C	109.5
C5—C6—C7	116.1 (2)	H15B—C15—H15C	109.5
O1—C7—N2	122.39 (19)	C10—C16—H16A	109.5
O1—C7—C6	121.75 (18)	C10—C16—H16B	109.5
N2—C7—C6	115.85 (19)	H16A—C16—H16B	109.5
N1—C8—N2	115.61 (17)	C10—C16—H16C	109.5
N1—C8—S1	125.52 (15)	H16A—C16—H16C	109.5
N2—C8—S1	118.87 (15)	H16B—C16—H16C	109.5
C6—C1—C2—C3	−0.2 (3)	C7—N2—C8—S1	−176.58 (17)
C1—C2—C3—C4	0.6 (4)	C8—N1—C9—C14	−83.0 (3)
C2—C3—C4—C5	−0.7 (4)	C8—N1—C9—C10	99.5 (2)
C3—C4—C5—C6	0.5 (4)	C14—C9—C10—C11	1.2 (3)
C2—C1—C6—C5	0.0 (3)	N1—C9—C10—C11	178.65 (19)
C2—C1—C6—C7	−177.5 (2)	C14—C9—C10—C16	−178.0 (2)
C4—C5—C6—C1	−0.1 (3)	N1—C9—C10—C16	−0.6 (3)
C4—C5—C6—C7	177.6 (2)	C9—C10—C11—C12	−1.5 (3)
C8—N2—C7—O1	−9.5 (3)	C16—C10—C11—C12	177.7 (2)
C8—N2—C7—C6	170.05 (19)	C10—C11—C12—C13	1.1 (4)
C1—C6—C7—O1	158.0 (2)	C11—C12—C13—C14	−0.2 (4)
C5—C6—C7—O1	−19.6 (3)	C10—C9—C14—C13	−0.4 (3)
C1—C6—C7—N2	−21.6 (3)	N1—C9—C14—C13	−177.77 (18)
C5—C6—C7—N2	160.81 (19)	C10—C9—C14—C15	−180.0 (2)
C9—N1—C8—N2	−169.15 (18)	N1—C9—C14—C15	2.6 (3)
C9—N1—C8—S1	10.1 (3)	C12—C13—C14—C9	−0.1 (3)
C7—N2—C8—N1	2.8 (3)	C12—C13—C14—C15	179.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.82 (2)	1.99 (2)	2.670 (2)	140 (2)
C13—H13···S1^i	0.98 (3)	2.94 (3)	3.862 (2)	157 (2)

Symmetry code: (i) −x+1, y−1/2, −z+3/2.