N-(4-Methoxy­benzoyl)-N′-(4-methoxy­phenyl)­thio­urea

Molecules of the title compound, C₁₆H₁₆N₂O₃S, are linked by N—H...S hydrogen bonds to form centrosymmetric dimers [N...S = 3.4501 (13) Å]. The N′-phenyl and N-phenyl rings are twisted by 52.7 (1) and 23.3 (1)°, respectively, from the essentially planar —NHC(=S)NC(=O)— moiety.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.132
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

N-(4-Methoxybenzoyl)-N'-(4-methoxyphenyl)thiourea

Crystal data

C16H16N2O3S	F(000) = 664
Mr = 316.37	Dx = 1.369 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3590 reflections
a = 11.4198 (7) Å	θ = 2.5–26.8°
b = 11.0121 (7) Å	µ = 0.23 mm^−1
c = 12.2262 (8) Å	T = 295 K
β = 93.319 (1)°	Block, colorless
V = 1534.94 (17) Å^3	0.44 × 0.40 × 0.24 mm
Z = 4

Data collection

Bruker SMART area-detector diffractometer	2369 reflections with I > 2σ(I)
Radiation source: medium-focus sealed tube	Rint = 0.019
Graphite monochromator	θmax = 27.1°, θmin = 1.8°
φ and ω scans	h = −14→14
9010 measured reflections	k = −14→13
3338 independent reflections	l = −15→7

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0728P)^2 + 0.3087P] where P = (Fo^2 + 2Fc^2)/3
3338 reflections	(Δ/σ)max = 0.001
209 parameters	Δρmax = 0.23 e Å^−3
2 restraints	Δρmin = −0.19 e Å^−3

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

	x	y	z	Uiso*/Ueq
S1	0.65003 (5)	0.56860 (5)	0.43628 (5)	0.0614 (2)
N1	0.6388 (1)	0.8077 (1)	0.4577 (1)	0.0464 (4)
N2	0.5108 (1)	0.6962 (1)	0.5565 (1)	0.0432 (4)
O1	0.9838 (1)	0.9425 (2)	0.1794 (1)	0.0700 (5)
O2	0.4909 (1)	0.8975 (1)	0.5931 (1)	0.0569 (4)
O3	0.1999 (2)	0.6879 (1)	0.9740 (1)	0.0686 (5)
C1	0.7323 (2)	0.8331 (2)	0.3887 (2)	0.0413 (4)
C2	0.7308 (2)	0.7934 (2)	0.2809 (2)	0.0510 (5)
C3	0.8174 (2)	0.8304 (2)	0.2148 (2)	0.0537 (5)
C4	0.9057 (2)	0.9065 (2)	0.2542 (2)	0.0491 (5)
C5	0.9088 (2)	0.9442 (2)	0.3612 (2)	0.0567 (5)
C6	0.8208 (2)	0.9069 (2)	0.4280 (2)	0.0523 (5)
C7	1.0673 (2)	1.0323 (3)	0.2130 (3)	0.0847 (8)
C8	0.5989 (2)	0.6983 (2)	0.4826 (2)	0.0414 (4)
C9	0.4681 (2)	0.7923 (2)	0.6154 (2)	0.0419 (4)
C10	0.3960 (2)	0.7609 (2)	0.7076 (2)	0.0403 (4)
C11	0.4006 (2)	0.6493 (2)	0.7611 (2)	0.0443 (4)
C12	0.3347 (2)	0.6288 (2)	0.8487 (2)	0.0500 (5)
C13	0.2616 (2)	0.7186 (2)	0.8862 (2)	0.0466 (4)
C14	0.2568 (2)	0.8303 (2)	0.8351 (2)	0.0522 (5)
C15	0.3240 (2)	0.8505 (2)	0.7471 (2)	0.0503 (5)
C16	0.1289 (3)	0.7778 (2)	1.0208 (2)	0.0767 (8)
H1n	0.603 (2)	0.867 (2)	0.488 (2)	0.067 (7)*
H2n	0.482 (2)	0.626 (1)	0.568 (2)	0.044 (5)*
H2	0.6715	0.7419	0.2535	0.061*
H3	0.8163	0.8037	0.1426	0.064*
H5	0.9691	0.9941	0.3890	0.068*
H6	0.8225	0.9327	0.5005	0.063*
H7a	1.1122	1.0545	0.1520	0.127*
H7b	1.1189	1.0007	0.2709	0.127*
H7c	1.0274	1.1026	0.2387	0.127*
H11	0.4491	0.5883	0.7369	0.053*
H12	0.3387	0.5538	0.8838	0.060*
H14	0.2087	0.8913	0.8599	0.063*
H15	0.3212	0.9262	0.7132	0.060*
H16a	0.0942	0.7449	1.0841	0.115*
H16b	0.0681	0.8025	0.9680	0.115*
H16c	0.1764	0.8468	1.0420	0.115*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0639 (4)	0.0392 (3)	0.0847 (4)	−0.0026 (2)	0.0353 (3)	−0.0050 (2)
N1	0.047 (1)	0.038 (1)	0.057 (1)	−0.003 (1)	0.019 (1)	−0.002 (1)
N2	0.046 (1)	0.035 (1)	0.050 (1)	−0.006 (1)	0.016 (1)	−0.001 (1)
O1	0.061 (1)	0.073 (1)	0.080 (1)	−0.010 (1)	0.040 (1)	−0.002 (1)
O2	0.072 (1)	0.037 (1)	0.065 (1)	−0.008 (1)	0.029 (1)	−0.002 (1)
O3	0.087 (1)	0.057 (1)	0.066 (1)	0.016 (1)	0.043 (1)	0.014 (1)
C1	0.040 (1)	0.037 (1)	0.048 (1)	−0.001 (1)	0.012 (1)	0.003 (1)
C2	0.047 (1)	0.055 (1)	0.051 (1)	−0.009 (1)	0.005 (1)	−0.002 (1)
C3	0.055 (1)	0.061 (1)	0.047 (1)	−0.002 (1)	0.013 (1)	−0.003 (1)
C4	0.042 (1)	0.047 (1)	0.061 (1)	0.005 (1)	0.020 (1)	0.005 (1)
C5	0.048 (1)	0.059 (1)	0.065 (1)	−0.01 (1)	0.014 (1)	−0.007 (1)
C6	0.054 (1)	0.053 (1)	0.051 (1)	−0.010 (1)	0.014 (1)	−0.007 (1)
C7	0.057 (1)	0.090 (2)	0.110 (2)	−0.019 (1)	0.036 (1)	0.009 (2)
C8	0.039 (1)	0.040 (1)	0.046 (1)	−0.003 (1)	0.009 (1)	0.001 (1)
C9	0.042 (1)	0.038 (1)	0.046 (1)	−0.003 (1)	0.008 (1)	−0.001 (1)
C10	0.042 (1)	0.036 (1)	0.044 (1)	−0.002 (1)	0.008 (1)	0.000 (1)
C11	0.049 (1)	0.035 (1)	0.049 (1)	0.005 (1)	0.012 (1)	0.000 (1)
C12	0.062 (1)	0.038 (1)	0.052 (1)	0.008 (1)	0.017 (1)	0.010 (1)
C13	0.053 (1)	0.045 (1)	0.044 (1)	0.002 (1)	0.014 (1)	0.002 (1)
C14	0.059 (1)	0.041 (1)	0.059 (1)	0.012 (1)	0.021 (1)	0.004 (1)
C15	0.058 (1)	0.035 (1)	0.059 (1)	0.007 (1)	0.019 (1)	0.008 (1)
C16	0.090 (2)	0.069 (2)	0.076 (2)	0.016 (1)	0.046 (1)	0.005 (1)

Geometric parameters (Å, º)

S1—C8	1.655 (2)	C12—C13	1.389 (3)
N1—C1	1.426 (2)	C13—C14	1.379 (3)
N1—C8	1.330 (2)	C14—C15	1.376 (3)
N2—C8	1.390 (2)	N1—H1n	0.86 (1)
N2—C9	1.385 (2)	N2—H2n	0.86 (1)
O1—C4	1.372 (2)	C2—H2	0.93
O1—C7	1.419 (3)	C3—H3	0.93
O2—C9	1.222 (2)	C5—H5	0.93
O3—C13	1.360 (2)	C6—H6	0.93
O3—C16	1.421 (3)	C7—H7a	0.96
C1—C6	1.363 (3)	C7—H7b	0.96
C1—C2	1.388 (3)	C7—H7c	0.96
C2—C3	1.374 (3)	C11—H11	0.93
C3—C4	1.377 (3)	C12—H12	0.93
C4—C5	1.371 (3)	C14—H14	0.93
C5—C6	1.392 (3)	C15—H15	0.93
C9—C10	1.475 (2)	C16—H16a	0.96
C10—C15	1.388 (2)	C16—H16b	0.96
C10—C11	1.391 (3)	C16—H16c	0.96
C11—C12	1.364 (3)
C1—N1—C8	126.3 (2)	C8—N1—H1n	114 (2)
C8—N2—C8	128.0 (2)	C1—N1—H1n	119 (2)
C4—O1—C7	117.4 (2)	C9—N2—H2n	117 (1)
C13—O3—C16	118.6 (2)	C8—N2—H2n	115 (1)
C6—C1—C2	119.4 (2)	C3—C2—H2	120.2
C6—C1—N1	118.3 (2)	C1—C2—H2	120.2
C2—C1—N1	122.1 (2)	C2—C3—H3	119.6
C3—C2—C1	119.7 (2)	C4—C3—H3	119.6
C2—C3—C4	120.8 (2)	C4—C5—H5	120.3
C5—C4—O1	124.5 (2)	C6—C5—H5	120.3
C5—C4—C3	119.7 (2)	C1—C6—H6	119.5
O1—C4—C3	115.7 (2)	C5—C6—H6	119.5
C4—C5—C6	119.4 (2)	O1—C7—H7a	109.5
C1—C6—C5	121.0 (2)	O1—C7—H7b	109.5
N1—C8—N2	115.7 (2)	H7a—C7—H7b	109.5
N1—C8—S1	124.8 (1)	O1—C7—H7c	109.5
N2—C8—S1	119.4 (1)	H7a—C7—H7c	109.5
O2—C9—N2	121.5 (2)	H7b—C7—H7c	109.5
O2—C9—C10	121.9 (2)	C12—C11—H11	119.7
N2—C9—C10	116.6 (2)	C10—C11—H11	119.7
C15—C10—C11	118.1 (2)	C11—C12—H12	119.6
C15—C10—C9	117.8 (2)	C13—C12—H12	119.6
C11—C10—C9	123.9 (2)	C15—C14—H14	120.3
C12—C11—C10	120.5 (2)	C13—C14—H14	120.3
C11—C12—C13	120.7 (2)	C10—C15—H15	119.2
O3—C13—C14	124.8 (2)	O3—C16—H16a	109.5
O3—C13—C12	115.6 (2)	O3—C16—H16b	109.5
C14—C13—C12	119.6 (2)	H16a—C16—H16b	109.5
C15—C14—C13	119.3 (2)	O3—C16—H16c	109.5
C14—C15—C10	121.7 (2)	H16a—C16—H16c	109.5
C14—C15—H15	119.2	H16b—C16—H16c	109.5
C8—N1—C1—C6	−127.9 (2)	C8—N2—C9—O2	13.4 (3)
C8—N1—C1—C2	57.4 (3)	C8—N2—C9—C10	−165.3 (2)
C6—C1—C2—C3	−1.1 (3)	O2—C9—C10—C15	20.1 (3)
N1—C1—C2—C3	173.6 (2)	N2—C9—C10—C15	−161.2 (2)
C1—C2—C3—C4	0.0 (3)	O2—C9—C10—C11	−156.1 (2)
C7—O1—C4—C5	−5.5 (3)	N2—C9—C10—C11	22.5 (3)
C7—O1—C4—C3	172.5 (2)	C15—C10—C11—C12	1.1 (3)
C2—C3—C4—C5	1.3 (3)	C9—C10—C11—C12	177.3 (2)
C2—C3—C4—O1	−176.8 (2)	C10—C11—C12—C13	0.0 (3)
O1—C4—C5—C6	176.4 (2)	C16—O3—C13—C14	−3.0 (3)
C3—C4—C5—C6	−1.4 (3)	C16—O3—C13—C12	176.2 (2)
C2—C1—C6—C5	0.9 (3)	C11—C12—C13—O3	180.0 (2)
N1—C1—C6—C5	−174.0 (2)	C11—C12—C13—C14	−0.8 (3)
C4—C5—C6—C1	0.4 (3)	O3—C13—C14—C15	179.7 (2)
C1—N1—C8—N2	176.7 (2)	C12—C13—C14—C15	0.5 (3)
C1—N1—C8—S1	−0.8 (3)	C13—C14—C15—C10	0.6 (3)
C9—N2—C8—N1	−7.1 (3)	C11—C10—C15—C14	−1.4 (3)
C9—N2—C8—S1	170.5 (2)	C9—C10—C15—C14	−177.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O2	0.86 (1)	1.90 (2)	2.626 (2)	141 (2)
N2—H2n···S1^i	0.86 (1)	2.62 (1)	3.450 (2)	165 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.