N-(4-Methoxy­benzoyl)-N'-o-tolyl­thio­urea

In the title compound, C₁₆H₁₆N₂O₂S, the p-methoxy­benzoyl and o-methyl­phenyl fragments are trans and cis, respectively, with respect to the thione group across the C-N bonds. The central carbonyl­thio­urea (N₂C₂SO) moiety makes dihedral angles with the p-methoxy­benzoyl and o-methyl­phenyl fragments of 16.58 (7) and 22.76 (8)°, respectively.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.038
• wR factor = 0.110
• Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSMU01_ALERT_1_C  The ratio of given/expected absorption coefficient lies
               outside the range 0.99 <> 1.01
            Calculated value of mu =     0.224
            Value of mu given      =     0.220
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     -   C8      ..       6.02 su

   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

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT and SADABS (Sheldrick, 1996); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

N-(p-Methoxybenzoyl)-N'-o-tolylthiourea

Crystal data

C16H16N2O2S	Z = 2
Mr = 300.37	F(000) = 316
Triclinic, P1	Dx = 1.345 Mg m^−3
a = 7.4923 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.7866 (14) Å	Cell parameters from 893 reflections
c = 14.406 (3) Å	θ = 2.9–26.0°
α = 94.492 (3)°	µ = 0.22 mm^−1
β = 102.639 (3)°	T = 273 K
γ = 113.064 (3)°	Block, colourless
V = 741.8 (2) Å^3	0.51 × 0.50 × 0.49 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2681 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.013
Graphite monochromator	θmax = 26.0°, θmin = 2.9°
Detector resolution: 83.66 pixels mm^-1	h = −9→9
ω scans	k = −9→9
7569 measured reflections	l = −17→17
2896 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0615P)^2 + 0.1424P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
2896 reflections	Δρmax = 0.17 e Å^−3
193 parameters	Δρmin = −0.21 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.023 (6)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.39806 (7)	1.00233 (5)	0.85178 (3)	0.05868 (17)
O1	0.1883 (2)	0.37063 (15)	0.84889 (8)	0.0645 (3)
O2	0.1875 (2)	0.26807 (18)	1.27889 (8)	0.0701 (4)
N1	0.30212 (18)	0.68141 (17)	0.91595 (9)	0.0468 (3)
H1	0.3386	0.7570	0.9702	0.056*
N2	0.2637 (2)	0.64815 (17)	0.75211 (9)	0.0497 (3)
H2	0.2214	0.5304	0.7572	0.060*
C1	0.2280 (2)	0.5559 (2)	1.09465 (11)	0.0482 (3)
H1A	0.2369	0.6767	1.0884	0.058*
C2	0.2142 (2)	0.4944 (2)	1.18054 (11)	0.0540 (4)
H2A	0.2147	0.5743	1.2322	0.065*
C3	0.1994 (2)	0.3142 (2)	1.19100 (11)	0.0514 (4)
C4	0.1976 (3)	0.1951 (2)	1.11394 (12)	0.0561 (4)
H4	0.1868	0.0737	1.1201	0.067*
C5	0.2118 (2)	0.2583 (2)	1.02783 (12)	0.0535 (4)
H5	0.2099	0.1779	0.9760	0.064*
C6	0.2289 (2)	0.4388 (2)	1.01674 (10)	0.0450 (3)
C7	0.2377 (2)	0.4916 (2)	0.92097 (11)	0.0475 (3)
C8	0.3164 (2)	0.7678 (2)	0.83517 (10)	0.0437 (3)
C9	0.2656 (2)	0.6825 (2)	0.65711 (10)	0.0467 (3)
C10	0.2758 (2)	0.5425 (2)	0.59439 (11)	0.0523 (4)
C11	0.2752 (3)	0.5703 (3)	0.50043 (13)	0.0667 (5)
H11	0.2811	0.4784	0.4575	0.080*
C12	0.2663 (3)	0.7282 (3)	0.46900 (13)	0.0752 (5)
H12	0.2683	0.7441	0.4058	0.090*
C13	0.2546 (3)	0.8634 (3)	0.53120 (13)	0.0735 (5)
H13	0.2483	0.9712	0.5101	0.088*
C14	0.2520 (3)	0.8405 (2)	0.62495 (12)	0.0611 (4)
H14	0.2411	0.9313	0.6664	0.073*
C15	0.1679 (3)	0.0833 (3)	1.29285 (16)	0.0797 (6)
H15A	0.0486	−0.0102	1.2470	0.120*
H15B	0.1579	0.0684	1.3573	0.120*
H15C	0.2838	0.0670	1.2837	0.120*
C16	0.2865 (3)	0.3668 (3)	0.62586 (14)	0.0706 (5)
H16A	0.3934	0.4017	0.6842	0.106*
H16B	0.3121	0.2978	0.5760	0.106*
H16C	0.1608	0.2884	0.6375	0.106*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0828 (3)	0.0373 (2)	0.0451 (2)	0.01898 (19)	0.01003 (19)	0.00215 (16)
O1	0.0988 (9)	0.0422 (6)	0.0501 (6)	0.0272 (6)	0.0214 (6)	0.0053 (5)
O2	0.0881 (9)	0.0650 (8)	0.0485 (7)	0.0235 (6)	0.0158 (6)	0.0180 (6)
N1	0.0566 (7)	0.0394 (6)	0.0398 (6)	0.0170 (5)	0.0116 (5)	0.0030 (5)
N2	0.0652 (8)	0.0378 (6)	0.0427 (6)	0.0192 (5)	0.0140 (5)	0.0039 (5)
C1	0.0492 (8)	0.0400 (7)	0.0486 (8)	0.0145 (6)	0.0090 (6)	0.0050 (6)
C2	0.0591 (9)	0.0491 (8)	0.0445 (8)	0.0167 (7)	0.0103 (6)	0.0013 (6)
C3	0.0462 (8)	0.0545 (9)	0.0456 (8)	0.0153 (6)	0.0073 (6)	0.0120 (7)
C4	0.0632 (9)	0.0488 (8)	0.0613 (10)	0.0270 (7)	0.0176 (7)	0.0171 (7)
C5	0.0642 (9)	0.0486 (8)	0.0529 (9)	0.0280 (7)	0.0186 (7)	0.0083 (7)
C6	0.0431 (7)	0.0424 (7)	0.0469 (8)	0.0167 (6)	0.0100 (6)	0.0074 (6)
C7	0.0511 (8)	0.0425 (7)	0.0475 (8)	0.0194 (6)	0.0123 (6)	0.0055 (6)
C8	0.0452 (7)	0.0413 (7)	0.0424 (7)	0.0173 (6)	0.0109 (6)	0.0040 (6)
C9	0.0493 (7)	0.0428 (7)	0.0413 (7)	0.0140 (6)	0.0116 (6)	0.0026 (6)
C10	0.0513 (8)	0.0468 (8)	0.0507 (8)	0.0154 (6)	0.0126 (6)	−0.0027 (6)
C11	0.0777 (12)	0.0666 (11)	0.0514 (9)	0.0259 (9)	0.0226 (8)	−0.0045 (8)
C12	0.1005 (14)	0.0743 (12)	0.0448 (9)	0.0282 (11)	0.0244 (9)	0.0109 (8)
C13	0.1108 (15)	0.0584 (10)	0.0488 (9)	0.0335 (10)	0.0194 (9)	0.0131 (8)
C14	0.0876 (12)	0.0500 (9)	0.0464 (8)	0.0308 (8)	0.0168 (8)	0.0057 (7)
C15	0.0945 (14)	0.0759 (13)	0.0674 (12)	0.0307 (11)	0.0210 (10)	0.0352 (10)
C16	0.0928 (13)	0.0562 (10)	0.0651 (11)	0.0369 (10)	0.0194 (9)	−0.0012 (8)

Geometric parameters (Å, º)

S1—C8	1.6608 (15)	C5—H5	0.9300
O1—C7	1.2282 (18)	C6—C7	1.478 (2)
O2—C3	1.3549 (19)	C9—C14	1.380 (2)
O2—C15	1.423 (2)	C9—C10	1.397 (2)
N1—C7	1.3767 (18)	C10—C11	1.387 (2)
N1—C8	1.3925 (19)	C10—C16	1.500 (2)
N1—H1	0.8600	C11—C12	1.363 (3)
N2—C8	1.3365 (18)	C11—H11	0.9300
N2—C9	1.4170 (19)	C12—C13	1.371 (3)
N2—H2	0.8600	C12—H12	0.9300
C1—C2	1.371 (2)	C13—C14	1.379 (2)
C1—C6	1.392 (2)	C13—H13	0.9300
C1—H1A	0.9300	C14—H14	0.9300
C2—C3	1.387 (2)	C15—H15A	0.9600
C2—H2A	0.9300	C15—H15B	0.9600
C3—C4	1.384 (2)	C15—H15C	0.9600
C4—C5	1.380 (2)	C16—H16A	0.9600
C4—H4	0.9300	C16—H16B	0.9600
C5—C6	1.386 (2)	C16—H16C	0.9600
C3—O2—C15	118.04 (15)	C14—C9—C10	120.40 (14)
C7—N1—C8	128.91 (12)	C14—C9—N2	123.44 (13)
C7—N1—H1	115.5	C10—C9—N2	116.14 (13)
C8—N1—H1	115.5	C11—C10—C9	117.65 (15)
C8—N2—C9	130.91 (12)	C11—C10—C16	120.26 (15)
C8—N2—H2	114.5	C9—C10—C16	122.09 (15)
C9—N2—H2	114.5	C12—C11—C10	122.13 (16)
C2—C1—C6	120.53 (14)	C12—C11—H11	118.9
C2—C1—H1A	119.7	C10—C11—H11	118.9
C6—C1—H1A	119.7	C11—C12—C13	119.47 (17)
C1—C2—C3	120.55 (14)	C11—C12—H12	120.3
C1—C2—H2A	119.7	C13—C12—H12	120.3
C3—C2—H2A	119.7	C12—C13—C14	120.41 (17)
O2—C3—C4	124.54 (15)	C12—C13—H13	119.8
O2—C3—C2	115.76 (15)	C14—C13—H13	119.8
C4—C3—C2	119.70 (14)	C13—C14—C9	119.91 (16)
C5—C4—C3	119.31 (15)	C13—C14—H14	120.0
C5—C4—H4	120.3	C9—C14—H14	120.0
C3—C4—H4	120.3	O2—C15—H15A	109.5
C4—C5—C6	121.59 (15)	O2—C15—H15B	109.5
C4—C5—H5	119.2	H15A—C15—H15B	109.5
C6—C5—H5	119.2	O2—C15—H15C	109.5
C5—C6—C1	118.31 (13)	H15A—C15—H15C	109.5
C5—C6—C7	117.57 (13)	H15B—C15—H15C	109.5
C1—C6—C7	124.05 (13)	C10—C16—H16A	109.5
O1—C7—N1	121.55 (14)	C10—C16—H16B	109.5
O1—C7—C6	121.17 (14)	H16A—C16—H16B	109.5
N1—C7—C6	117.27 (12)	C10—C16—H16C	109.5
N2—C8—N1	114.51 (12)	H16A—C16—H16C	109.5
N2—C8—S1	127.60 (11)	H16B—C16—H16C	109.5
N1—C8—S1	117.89 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···S1	0.93	2.59	3.1895 (18)	123
N2—H2···O1	0.86	1.87	2.6063 (17)	142
N1—H1···S1^i	0.86	2.85	3.6596 (15)	158
C1—H1A···S1^i	0.93	2.78	3.3712 (17)	122

Symmetry code: (i) −x+1, −y+2, −z+2.