1,3-Bis(4-methoxy­phen­yl)thio­urea

In the crystal structure of the title compound, C₁₅H₁₆N₂O₂S, the The C=S group lies on a mirror plane. The mol­ecules are packed in a centrosymmetric manner through inter­molecular N—H...S hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 290 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.054
• wR factor = 0.127
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).

1,3-Bis(4-methoxyphenyl)thiourea

Crystal data

C15H16N2O2S	Dx = 1.358 Mg m^−3
Mr = 288.37	Melting point: 202 K
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 732 reflections
a = 8.427 (5) Å	θ = 2.6–27.4°
b = 31.628 (19) Å	µ = 0.23 mm^−1
c = 5.292 (3) Å	T = 290 K
V = 1410.3 (14) Å^3	Prism, colourless
Z = 4	0.45 × 0.40 × 0.35 mm
F(000) = 608

Data collection

Bruker SMART CCD area-detector diffractometer	1572 independent reflections
Radiation source: fine-focus sealed tube	1433 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 27.4°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.903, Tmax = 0.923	k = −40→39
11344 measured reflections	l = −6→6

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.127	All H-atom parameters refined
S = 1.21	w = 1/[σ^2(Fo^2) + (0.0502P)^2 + 0.7475P] where P = (Fo^2 + 2Fc^2)/3
1572 reflections	(Δ/σ)max < 0.001
126 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.30058 (9)	0.25000	0.61989 (16)	0.0457 (3)
O1	0.3347 (2)	0.05014 (5)	0.5625 (4)	0.0607 (6)
N1	0.5326 (2)	0.21436 (5)	0.3520 (4)	0.0451 (6)
C1	0.4633 (3)	0.25000	0.4324 (5)	0.0369 (8)
C2	0.4809 (2)	0.17261 (6)	0.4159 (4)	0.0388 (6)
C3	0.3743 (3)	0.15207 (7)	0.2602 (5)	0.0452 (7)
C4	0.3264 (3)	0.11132 (7)	0.3169 (5)	0.0487 (7)
C5	0.3881 (3)	0.09076 (6)	0.5254 (4)	0.0427 (6)
C6	0.4958 (3)	0.11110 (7)	0.6804 (4)	0.0458 (7)
C7	0.5404 (3)	0.15240 (7)	0.6258 (4)	0.0449 (7)
C8	0.4002 (4)	0.02715 (9)	0.7674 (7)	0.0700 (10)
H1	0.603 (3)	0.2163 (8)	0.251 (5)	0.054 (7)*
H3	0.336 (3)	0.1655 (8)	0.120 (5)	0.053 (7)*
H4	0.257 (3)	0.0981 (8)	0.219 (5)	0.061 (7)*
H6	0.536 (3)	0.0990 (8)	0.825 (5)	0.053 (7)*
H7	0.614 (3)	0.1661 (8)	0.730 (5)	0.050 (6)*
H8A	0.377 (4)	0.0421 (10)	0.940 (6)	0.084 (10)*
H8B	0.518 (4)	0.0246 (10)	0.754 (6)	0.086 (10)*
H8C	0.354 (4)	0.0004 (10)	0.765 (6)	0.077 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0436 (4)	0.0384 (4)	0.0551 (5)	0.0000	0.0144 (3)	0.0000
O1	0.0656 (11)	0.0357 (8)	0.0807 (12)	−0.0093 (7)	−0.0080 (9)	0.0056 (8)
N1	0.0434 (10)	0.0353 (9)	0.0567 (11)	−0.0005 (7)	0.0165 (9)	−0.0012 (8)
C1	0.0370 (14)	0.0353 (14)	0.0384 (14)	0.0000	−0.0014 (12)	0.0000
C2	0.0382 (10)	0.0297 (9)	0.0485 (11)	0.0016 (8)	0.0092 (9)	−0.0025 (8)
C3	0.0455 (12)	0.0395 (11)	0.0507 (12)	0.0061 (9)	−0.0036 (10)	0.0018 (10)
C4	0.0466 (12)	0.0406 (11)	0.0589 (14)	−0.0044 (9)	−0.0093 (11)	−0.0064 (10)
C5	0.0414 (11)	0.0318 (10)	0.0548 (12)	−0.0003 (8)	0.0045 (10)	−0.0024 (9)
C6	0.0492 (12)	0.0440 (12)	0.0441 (12)	−0.0026 (10)	−0.0010 (10)	0.0051 (9)
C7	0.0463 (12)	0.0434 (11)	0.0451 (12)	−0.0081 (9)	−0.0001 (10)	−0.0043 (9)
C8	0.084 (2)	0.0420 (13)	0.084 (2)	−0.0078 (14)	0.0002 (17)	0.0162 (14)

Geometric parameters (Å, º)

S1—C1	1.693 (3)	C5—C6	1.382 (3)
O1—C5	1.375 (3)	C6—C7	1.390 (3)
O1—C8	1.417 (4)	C3—H3	0.91 (3)
N1—C1	1.339 (2)	C4—H4	0.89 (3)
N1—C2	1.431 (3)	C6—H6	0.92 (3)
N1—H1	0.80 (3)	C7—H7	0.93 (3)
C2—C7	1.376 (3)	C8—H8A	1.05 (3)
C2—C3	1.381 (3)	C8—H8B	1.00 (3)
C3—C4	1.384 (3)	C8—H8C	0.93 (3)
C4—C5	1.382 (3)
S1···C3	3.688 (3)	C7···H3^vii	2.84 (3)
S1···C7	3.690 (3)	C8···H6	2.56 (3)
S1···C3^i	3.688 (3)	C8···H8B^x	3.09 (3)
S1···C7^i	3.690 (3)	H1···S1^xi	2.79 (3)
S1···H1^ii	2.79 (3)	H1···S1^vii	2.79 (3)
S1···H7^iii	3.19 (3)	H1···C3^vii	3.06 (3)
S1···H7^iv	3.19 (3)	H1···H1^i	2.13 (4)
S1···H1^v	2.79 (3)	H3···C2^v	3.01 (3)
O1···H8C^vi	2.75 (3)	H3···C7^v	2.84 (3)
C2···C3^vii	3.504 (4)	H4···H8A^viii	2.52 (4)
C3···C2^v	3.504 (4)	H4···C6^v	3.08 (3)
C3···S1	3.688 (3)	H6···C8	2.56 (3)
C3···C6^viii	3.485 (4)	H6···H8A	2.32 (4)
C3···C7^v	3.477 (4)	H6···H8B	2.39 (4)
C6···C3^ix	3.485 (4)	H6···C5^xii	3.08 (3)
C7···C3^vii	3.477 (4)	H7···S1^xiii	3.19 (3)
C7···S1	3.690 (3)	H7···S1^xii	3.19 (3)
C8···C8^x	3.441 (5)	H8A···C4^ix	2.99 (3)
C2···H3^vii	3.01 (3)	H8A···C6	2.77 (3)
C3···H1^v	3.06 (3)	H8A···H4^ix	2.52 (4)
C4···H8A^viii	2.99 (3)	H8A···H6	2.32 (4)
C5···H6^iii	3.08 (3)	H8B···C6	2.77 (3)
C6···H4^vii	3.08 (3)	H8B···H6	2.39 (4)
C6···H8B	2.77 (3)	H8B···C8^x	3.09 (3)
C6···H8A	2.77 (3)	H8C···O1^xiv	2.75 (3)
C5—O1—C8	117.5 (2)	C2—C7—C6	120.4 (2)
C1—N1—C2	124.68 (18)	C2—C3—H3	119.7 (16)
C2—N1—H1	117.0 (18)	C4—C3—H3	120.4 (16)
C1—N1—H1	118.1 (18)	C3—C4—H4	120.4 (17)
S1—C1—N1^i	122.66 (12)	C5—C4—H4	119.5 (17)
N1—C1—N1^i	114.7 (2)	C5—C6—H6	122.8 (16)
S1—C1—N1	122.66 (12)	C7—C6—H6	117.7 (16)
C3—C2—C7	120.00 (19)	C2—C7—H7	120.3 (16)
N1—C2—C3	119.41 (19)	C6—C7—H7	119.3 (16)
N1—C2—C7	120.56 (18)	O1—C8—H8A	111.3 (18)
C2—C3—C4	119.9 (2)	O1—C8—H8B	112.0 (18)
C3—C4—C5	120.1 (2)	O1—C8—H8C	107 (2)
O1—C5—C6	124.4 (2)	H8A—C8—H8B	107 (3)
O1—C5—C4	115.5 (2)	H8A—C8—H8C	110 (3)
C4—C5—C6	120.12 (19)	H8B—C8—H8C	110 (3)
C5—C6—C7	119.5 (2)
C8—O1—C5—C4	177.2 (2)	C7—C2—C3—C4	0.6 (3)
C8—O1—C5—C6	−2.9 (4)	C3—C2—C7—C6	1.0 (3)
C1—N1—C2—C3	91.8 (3)	C2—C3—C4—C5	−1.6 (4)
C1—N1—C2—C7	−90.3 (3)	C3—C4—C5—O1	−179.0 (2)
C2—N1—C1—S1	−1.0 (3)	C3—C4—C5—C6	1.1 (4)
C2—N1—C1—N1^i	179.2 (2)	O1—C5—C6—C7	−179.5 (2)
N1—C2—C7—C6	−176.8 (2)	C4—C5—C6—C7	0.5 (4)
N1—C2—C3—C4	178.5 (2)	C5—C6—C7—C2	−1.5 (4)

Symmetry codes: (i) x, −y+1/2, z; (ii) x−1/2, −y+1/2, −z+1/2; (iii) x−1/2, y, −z+3/2; (iv) x−1/2, −y+1/2, −z+3/2; (v) x−1/2, y, −z+1/2; (vi) −x+1/2, −y, z−1/2; (vii) x+1/2, y, −z+1/2; (viii) x, y, z−1; (ix) x, y, z+1; (x) −x+1, −y, −z+2; (xi) x+1/2, −y+1/2, −z+1/2; (xii) x+1/2, y, −z+3/2; (xiii) x+1/2, −y+1/2, −z+3/2; (xiv) −x+1/2, −y, z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1^xi	0.80 (3)	2.79 (3)	3.551 (3)	160 (2)
N1—H1···S1^vii	0.80 (3)	2.79 (3)	3.551 (3)	160 (2)

Symmetry codes: (vii) x+1/2, y, −z+1/2; (xi) x+1/2, −y+1/2, −z+1/2.