Redetermination of 1-benzyl-3-furoyl-1-phenyl-thio-urea.

The title compound, C(19)H(16)N(2)O(2)S, was synthesized from furoyl isothio-cyanate and N-benzyl-aniline in dry acetone and the structure redetermined. The structure [Otazo-Sánchez et al. (2001 ▶). J. Chem. Soc. Perkin Trans. 2, pp. 2211-2218] has been re-determined in order to establish the intramolecular and intermolecular inter-actions. The thio-urea group is in the thio-amide form. The thio-urea group makes a dihedral angle of 29.2 (6)° with the furoyl group. In the crystal structure, mol-ecules are linked by inter-molecular C-H⋯O inter-actions, forming one-dimensional chains along the a axis. An intra-molecular N-H⋯O hydrogen bond is also present.

Related literature

For general background, see: Aly et al. (2007 ▶), Koch (2001 ▶), Estévez-Hernández et al. (2006 ▶). For related structures, see: Pérez et al. (2008 ▶). For the synthesis, see: Otazo-Sánchez et al. (2001 ▶).

Experimental

Crystal data

C19H16N2O2S

M = 336.41

Orthorhombic,

a = 12.7737 (3) Å

b = 8.8047 (2) Å

c = 31.2345 (7) Å

V = 3512.90 (14) Å3

Z = 8

Mo Kα radiation

μ = 0.20 mm−1

T = 294 (2) K

0.54 × 0.22 × 0.19 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: gaussian (Coppens et al., 1965 ▶) T min = 0.92, T max = 0.971

19732 measured reflections

3536 independent reflections

2565 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.114

S = 1.03

3536 reflections

281 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.12 e Å−3

Δρmin = −0.13 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Bruno et al., 2002 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808044085/bq2112sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808044085/bq2112Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H16N2O2S	F(000) = 1408
Mr = 336.41	Dx = 1.272 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 19732 reflections
a = 12.7737 (3) Å	θ = 2.9–26.4°
b = 8.8047 (2) Å	µ = 0.20 mm−1
c = 31.2345 (7) Å	T = 294 K
V = 3512.90 (14) Å3	Prism, yellow
Z = 8	0.54 × 0.22 × 0.19 mm

Nonius KappaCCD diffractometer	2565 reflections with I > 2σ(I)
CCD rotation images, thick slices scans	Rint = 0.058
Absorption correction: gaussian (Coppens et al., 1965)	θmax = 26.4°, θmin = 3.1°
Tmin = 0.92, Tmax = 0.971	h = −15→15
19732 measured reflections	k = −11→8
3536 independent reflections	l = −38→39

Refinement on F2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.041	w = 1/[σ2(Fo2) + (0.0583P)2 + 0.343P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.114	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.12 e Å−3
3536 reflections	Δρmin = −0.13 e Å−3
281 parameters

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.

	x	y	z	Uiso*/Ueq
C1	0.26117 (12)	0.19869 (17)	0.05040 (4)	0.0577 (4)
C2	0.26889 (12)	0.37199 (18)	0.11358 (4)	0.0577 (4)
C3	0.32563 (12)	0.1570 (2)	0.01356 (5)	0.0619 (4)
C4	0.31207 (19)	0.0530 (3)	−0.01689 (6)	0.0842 (6)
C5	0.39938 (19)	0.0609 (3)	−0.04428 (7)	0.0952 (7)
C6	0.46044 (18)	0.1672 (3)	−0.02896 (6)	0.0861 (6)
C7	0.45449 (12)	0.39652 (19)	0.13227 (5)	0.0599 (4)
C8	0.51367 (15)	0.5088 (2)	0.11332 (6)	0.0723 (5)
C9	0.61918 (16)	0.4856 (3)	0.10720 (7)	0.0865 (6)
C10	0.66461 (18)	0.3518 (3)	0.11944 (7)	0.0909 (6)
C11	0.60580 (16)	0.2400 (3)	0.13808 (7)	0.0866 (6)
C12	0.50023 (15)	0.2623 (2)	0.14502 (6)	0.0747 (5)
C13	0.32176 (18)	0.5218 (2)	0.17699 (6)	0.0706 (4)
C14	0.34629 (12)	0.44677 (18)	0.21911 (5)	0.0615 (4)
C15	0.28076 (19)	0.3390 (3)	0.23609 (6)	0.0877 (6)
C16	0.3022 (3)	0.2697 (3)	0.27438 (8)	0.1152 (9)
C17	0.3882 (3)	0.3076 (3)	0.29671 (8)	0.1110 (9)
C18	0.4556 (2)	0.4131 (4)	0.28073 (8)	0.1023 (8)
C19	0.43495 (17)	0.4839 (3)	0.24164 (6)	0.0822 (5)
N1	0.30881 (11)	0.30009 (16)	0.07753 (4)	0.0607 (4)
N2	0.34480 (10)	0.42232 (15)	0.14007 (4)	0.0613 (3)
O1	0.17529 (9)	0.14370 (14)	0.05539 (4)	0.0732 (3)
O2	0.41816 (9)	0.23024 (15)	0.00713 (4)	0.0762 (3)
S1	0.14167 (3)	0.39752 (6)	0.121403 (14)	0.07098 (18)
H1	0.3720 (15)	0.319 (2)	0.0721 (6)	0.078 (6)*
H4	0.2628 (18)	0.001 (3)	−0.0187 (6)	0.092 (7)*
H5	0.4127 (17)	0.003 (3)	−0.0693 (7)	0.109 (7)*
H6	0.5238 (18)	0.211 (3)	−0.0356 (7)	0.107 (7)*
H8	0.4814 (14)	0.597 (2)	0.1052 (5)	0.075 (5)*
H9	0.660 (2)	0.558 (3)	0.0925 (8)	0.120 (8)*
H10	0.734 (2)	0.335 (3)	0.1144 (8)	0.133 (9)*
H11	0.6356 (17)	0.143 (3)	0.1469 (7)	0.108 (7)*
H12	0.4597 (16)	0.188 (2)	0.1588 (6)	0.088 (6)*
H13A	0.3612 (15)	0.614 (2)	0.1742 (6)	0.081 (6)*
H13B	0.2478 (17)	0.544 (2)	0.1764 (5)	0.082 (5)*
H15	0.2202 (18)	0.315 (3)	0.2208 (7)	0.112 (8)*
H16	0.255 (3)	0.181 (4)	0.2858 (10)	0.180 (12)*
H17	0.404 (2)	0.260 (3)	0.3255 (9)	0.131 (8)*
H18	0.510 (2)	0.441 (3)	0.2933 (8)	0.130 (10)*
H19	0.4794 (17)	0.555 (3)	0.2293 (7)	0.103 (7)*

	U11	U22	U33	U12	U13	U23
C1	0.0526 (8)	0.0640 (9)	0.0563 (8)	0.0003 (7)	−0.0034 (6)	0.0060 (7)
C2	0.0570 (9)	0.0602 (9)	0.0560 (8)	0.0011 (7)	0.0010 (6)	0.0069 (7)
C3	0.0551 (8)	0.0738 (10)	0.0569 (8)	−0.0019 (8)	−0.0019 (7)	0.0037 (8)
C4	0.0826 (14)	0.0989 (16)	0.0711 (11)	−0.0108 (13)	−0.0020 (10)	−0.0153 (10)
C5	0.1014 (16)	0.1183 (18)	0.0659 (11)	0.0129 (14)	0.0064 (11)	−0.0178 (12)
C6	0.0735 (12)	0.1153 (17)	0.0695 (11)	0.0085 (12)	0.0163 (10)	0.0017 (11)
C7	0.0562 (9)	0.0675 (10)	0.0559 (8)	0.0011 (8)	−0.0065 (7)	−0.0052 (7)
C8	0.0659 (11)	0.0739 (12)	0.0772 (11)	0.0012 (9)	−0.0067 (8)	0.0021 (9)
C9	0.0644 (12)	0.0936 (15)	0.1013 (14)	−0.0087 (11)	0.0005 (10)	0.0047 (12)
C10	0.0557 (11)	0.1095 (18)	0.1075 (15)	0.0044 (12)	−0.0053 (10)	−0.0069 (13)
C11	0.0733 (13)	0.0878 (15)	0.0988 (14)	0.0177 (11)	−0.0119 (11)	−0.0013 (12)
C12	0.0697 (11)	0.0729 (12)	0.0814 (11)	0.0032 (10)	−0.0052 (9)	0.0025 (9)
C13	0.0747 (12)	0.0698 (12)	0.0674 (10)	0.0067 (10)	−0.0003 (9)	−0.0074 (8)
C14	0.0624 (9)	0.0622 (9)	0.0600 (8)	0.0016 (8)	0.0025 (7)	−0.0115 (7)
C15	0.0932 (14)	0.1008 (15)	0.0691 (11)	−0.0237 (12)	0.0073 (10)	−0.0063 (10)
C16	0.157 (3)	0.115 (2)	0.0739 (13)	−0.0213 (18)	0.0218 (16)	0.0066 (13)
C17	0.161 (3)	0.1054 (19)	0.0661 (13)	0.0328 (19)	0.0046 (15)	0.0021 (13)
C18	0.0984 (17)	0.126 (2)	0.0826 (14)	0.0257 (15)	−0.0288 (13)	−0.0254 (14)
C19	0.0754 (12)	0.0875 (13)	0.0838 (12)	−0.0046 (11)	−0.0083 (10)	−0.0092 (11)
N1	0.0489 (7)	0.0748 (9)	0.0584 (7)	−0.0047 (6)	0.0032 (6)	−0.0032 (6)
N2	0.0592 (8)	0.0697 (8)	0.0552 (7)	0.0047 (6)	−0.0013 (6)	−0.0031 (6)
O1	0.0583 (6)	0.0822 (8)	0.0791 (7)	−0.0113 (6)	0.0047 (5)	−0.0040 (6)
O2	0.0632 (7)	0.0934 (9)	0.0719 (7)	−0.0070 (6)	0.0097 (5)	−0.0042 (6)
S1	0.0554 (3)	0.0834 (3)	0.0741 (3)	0.0051 (2)	0.00711 (18)	−0.0001 (2)

C1—O1	1.2092 (18)	C10—C11	1.368 (3)
C1—N1	1.3731 (19)	C10—H10	0.91 (3)
C1—C3	1.462 (2)	C11—C12	1.380 (3)
C2—N2	1.349 (2)	C11—H11	0.97 (2)
C2—N1	1.389 (2)	C12—H12	0.94 (2)
C2—S1	1.6586 (16)	C13—N2	1.478 (2)
C3—C4	1.332 (3)	C13—C14	1.505 (2)
C3—O2	1.361 (2)	C13—H13A	0.96 (2)
C4—C5	1.407 (3)	C13—H13B	0.97 (2)
C4—H4	0.78 (2)	C14—C15	1.372 (3)
C5—C6	1.309 (3)	C14—C19	1.373 (2)
C5—H5	0.95 (2)	C15—C16	1.370 (3)
C6—O2	1.368 (2)	C15—H15	0.93 (2)
C6—H6	0.92 (2)	C16—C17	1.344 (4)
C7—C12	1.377 (2)	C16—H16	1.05 (4)
C7—C8	1.378 (2)	C17—C18	1.361 (4)
C7—N2	1.440 (2)	C17—H17	1.01 (3)
C8—C9	1.376 (3)	C18—C19	1.396 (3)
C8—H8	0.917 (19)	C18—H18	0.84 (3)
C9—C10	1.368 (3)	C19—H19	0.93 (2)
C9—H9	0.94 (3)	N1—H1	0.841 (19)
O1—C1—N1	125.65 (14)	C7—C12—H12	119.7 (13)
O1—C1—C3	120.79 (14)	C11—C12—H12	120.8 (13)
N1—C1—C3	113.54 (13)	N2—C13—C14	112.36 (14)
N2—C2—N1	112.52 (14)	N2—C13—H13A	109.1 (11)
N2—C2—S1	124.70 (12)	C14—C13—H13A	110.0 (11)
N1—C2—S1	122.74 (12)	N2—C13—H13B	107.6 (11)
C4—C3—O2	109.47 (16)	C14—C13—H13B	108.1 (10)
C4—C3—C1	131.42 (17)	H13A—C13—H13B	109.7 (17)
O2—C3—C1	119.10 (14)	C15—C14—C19	118.04 (19)
C3—C4—C5	107.3 (2)	C15—C14—C13	120.96 (17)
C3—C4—H4	123.9 (16)	C19—C14—C13	121.00 (18)
C5—C4—H4	128.8 (16)	C16—C15—C14	121.6 (2)
C6—C5—C4	106.6 (2)	C16—C15—H15	120.8 (15)
C6—C5—H5	125.4 (14)	C14—C15—H15	117.6 (15)
C4—C5—H5	128.0 (14)	C17—C16—C15	120.4 (3)
C5—C6—O2	110.87 (19)	C17—C16—H16	118.4 (18)
C5—C6—H6	137.7 (14)	C15—C16—H16	121.1 (19)
O2—C6—H6	111.4 (14)	C16—C17—C18	119.8 (2)
C12—C7—C8	120.46 (17)	C16—C17—H17	121.5 (15)
C12—C7—N2	119.95 (15)	C18—C17—H17	118.7 (15)
C8—C7—N2	119.55 (15)	C17—C18—C19	120.4 (2)
C9—C8—C7	119.4 (2)	C17—C18—H18	123.7 (19)
C9—C8—H8	121.8 (12)	C19—C18—H18	115.9 (19)
C7—C8—H8	118.8 (11)	C14—C19—C18	119.8 (2)
C10—C9—C8	120.3 (2)	C14—C19—H19	117.0 (13)
C10—C9—H9	119.0 (15)	C18—C19—H19	123.2 (13)
C8—C9—H9	120.6 (15)	C1—N1—C2	129.35 (14)
C11—C10—C9	120.4 (2)	C1—N1—H1	115.3 (12)
C11—C10—H10	119.4 (17)	C2—N1—H1	115.3 (12)
C9—C10—H10	120.2 (17)	C2—N2—C7	122.93 (13)
C10—C11—C12	120.0 (2)	C2—N2—C13	122.01 (14)
C10—C11—H11	122.4 (13)	C7—N2—C13	114.78 (14)
C12—C11—H11	117.6 (13)	C3—O2—C6	105.79 (15)
C7—C12—C11	119.5 (2)
O1—C1—C3—C4	−6.5 (3)	C16—C17—C18—C19	1.1 (4)
N1—C1—C3—C4	172.34 (19)	C15—C14—C19—C18	−0.4 (3)
O1—C1—C3—O2	174.73 (14)	C13—C14—C19—C18	179.69 (18)
N1—C1—C3—O2	−6.5 (2)	C17—C18—C19—C14	−0.1 (3)
O2—C3—C4—C5	−0.6 (2)	O1—C1—N1—C2	−6.2 (3)
C1—C3—C4—C5	−179.47 (18)	C3—C1—N1—C2	175.04 (15)
C3—C4—C5—C6	0.4 (3)	N2—C2—N1—C1	159.13 (15)
C4—C5—C6—O2	−0.1 (3)	S1—C2—N1—C1	−23.1 (2)
C12—C7—C8—C9	0.0 (3)	N1—C2—N2—C7	−2.9 (2)
N2—C7—C8—C9	177.88 (16)	S1—C2—N2—C7	179.43 (12)
C7—C8—C9—C10	0.6 (3)	N1—C2—N2—C13	170.71 (14)
C8—C9—C10—C11	−0.3 (3)	S1—C2—N2—C13	−7.0 (2)
C9—C10—C11—C12	−0.6 (3)	C12—C7—N2—C2	−84.39 (19)
C8—C7—C12—C11	−1.0 (3)	C8—C7—N2—C2	97.73 (19)
N2—C7—C12—C11	−178.84 (16)	C12—C7—N2—C13	101.60 (18)
C10—C11—C12—C7	1.3 (3)	C8—C7—N2—C13	−76.27 (18)
N2—C13—C14—C15	−76.7 (2)	C14—C13—N2—C2	115.66 (17)
N2—C13—C14—C19	103.2 (2)	C14—C13—N2—C7	−70.3 (2)
C19—C14—C15—C16	0.0 (3)	C4—C3—O2—C6	0.5 (2)
C13—C14—C15—C16	179.9 (2)	C1—C3—O2—C6	179.59 (15)
C14—C15—C16—C17	0.9 (4)	C5—C6—O2—C3	−0.3 (2)
C15—C16—C17—C18	−1.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.84 (2)	2.25 (2)	2.677 (2)	111 (2)
C6—H6···O1i	0.92 (2)	2.40 (2)	3.315 (3)	172 (2)
C8—H8···O1ii	0.92 (2)	2.57 (2)	3.242 (2)	131 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.84 (2)	2.25 (2)	2.677 (2)	111 (2)
C6—H6⋯O1i	0.92 (2)	2.40 (2)	3.315 (3)	172 (2)
C8—H8⋯O1ii	0.92 (2)	2.57 (2)	3.242 (2)	131 (2)

Symmetry codes: (i) ; (ii) .