1-(Benzothia-zol-2-yl)-3-(4-nitro-benzo-yl)thio-urea.

The mol-ecule of the title compound, C(15)H(10)N(4)O(3)S(2), is almost planar (r.m.s. deviation = 0.1Å for all non-H atoms). An intra-molecular N-H⋯O=C hydrogen bond is observed. In the crystal, mol-ecules are connected into layers parallel to (10) by a classical inter-molecular hydrogen bond from the second NH group to a nitro O atom and by three weak hydrogen bonds of the C-H⋯X type (X = O or S(thione)).

Related literature

For general background to the chemistry of thio­urea derivatives, see Choi et al. (2008 ▶); Jones et al. (2008 ▶); Su et al. (2006 ▶). For related structures, see: Saeed et al. (2008a ▶,b ▶,c ▶); Yunus et al. (2008 ▶).

Experimental

Crystal data

C15H10N4O3S2

M = 358.39

Monoclinic,

a = 7.1596 (3) Å

b = 17.9071 (5) Å

c = 11.5768 (4) Å

β = 96.446 (4)°

V = 1474.85 (9) Å3

Z = 4

Cu Kα radiation

μ = 3.50 mm−1

T = 100 K

0.20 × 0.10 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur Nova A diffractometer

Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 ▶) T min = 0.682, T max = 1.000 (expected range = 0.573–0.840)

30943 measured reflections

3026 independent reflections

2834 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.078

S = 1.06

3026 reflections

225 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Siemens, 1994 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809030803/im2131sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030803/im2131Isup2.hkl

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

C15H10N4O3S2	F(000) = 736
Mr = 358.39	Dx = 1.614 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 21284 reflections
a = 7.1596 (3) Å	θ = 3.8–75.7°
b = 17.9071 (5) Å	µ = 3.50 mm−1
c = 11.5768 (4) Å	T = 100 K
β = 96.446 (4)°	Lath, yellow
V = 1474.85 (9) Å3	0.20 × 0.10 × 0.05 mm
Z = 4

Oxford Diffraction Xcalibur Nova A diffractometer	3026 independent reflections
Radiation source: Nova (Cu) X-ray Source	2834 reflections with I > 2σ(I)
mirror	Rint = 0.040
Detector resolution: 10.3543 pixels mm-1	θmax = 75.9°, θmin = 4.6°
ω scans	h = −8→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −22→22
Tmin = 0.682, Tmax = 1.000	l = −14→14
30943 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0427P)2 + 0.7178P] where P = (Fo2 + 2Fc2)/3
3026 reflections	(Δ/σ)max = 0.001
225 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.53606 (4)	0.470055 (17)	0.84776 (3)	0.01726 (10)
C2	0.44766 (17)	0.43337 (7)	0.71218 (11)	0.0165 (3)
N3	0.45826 (16)	0.36156 (6)	0.69808 (10)	0.0194 (2)
C3A	0.54057 (19)	0.32891 (8)	0.80022 (12)	0.0190 (3)
C4	0.5778 (2)	0.25256 (8)	0.81532 (13)	0.0232 (3)
H4	0.5452	0.2182	0.7538	0.028*
C5	0.6629 (2)	0.22814 (8)	0.92178 (13)	0.0248 (3)
H5	0.6894	0.1765	0.9331	0.030*
C6	0.7108 (2)	0.27842 (8)	1.01331 (12)	0.0234 (3)
H6	0.7681	0.2602	1.0859	0.028*
C7	0.67605 (19)	0.35414 (8)	0.99963 (12)	0.0209 (3)
H7	0.7094	0.3883	1.0614	0.025*
C7A	0.59024 (18)	0.37870 (7)	0.89188 (12)	0.0178 (3)
S2	0.43025 (6)	0.610190 (19)	0.71210 (3)	0.02877 (12)
N1	0.36489 (16)	0.47552 (6)	0.61966 (10)	0.0173 (2)
H01	0.316 (3)	0.4498 (11)	0.5646 (16)	0.029 (5)*
N2	0.25433 (16)	0.57570 (6)	0.50564 (10)	0.0179 (2)
H02	0.260 (3)	0.6224 (11)	0.5014 (16)	0.028 (5)*
N4	−0.17337 (16)	0.67589 (7)	0.00397 (10)	0.0215 (2)
O1	0.15674 (15)	0.46515 (5)	0.42156 (8)	0.0227 (2)
O2	−0.20909 (16)	0.74281 (6)	0.00649 (9)	0.0300 (3)
O3	−0.19731 (17)	0.63730 (6)	−0.08377 (9)	0.0314 (3)
C8	0.34765 (18)	0.55045 (7)	0.61124 (12)	0.0183 (3)
C9	0.16239 (18)	0.53355 (7)	0.41710 (11)	0.0174 (3)
C10	0.07004 (18)	0.57425 (7)	0.31352 (11)	0.0168 (3)
C11	0.04521 (19)	0.65149 (7)	0.30881 (12)	0.0194 (3)
H11	0.0855	0.6812	0.3749	0.023*
C12	−0.03826 (19)	0.68511 (8)	0.20783 (12)	0.0200 (3)
H12	−0.0567	0.7376	0.2040	0.024*
C13	−0.09376 (18)	0.64017 (7)	0.11316 (11)	0.0177 (3)
C14	−0.07437 (19)	0.56315 (8)	0.11565 (11)	0.0188 (3)
H14	−0.1166	0.5338	0.0495	0.023*
C15	0.00793 (19)	0.53013 (7)	0.21676 (12)	0.0186 (3)
H15	0.0224	0.4774	0.2207	0.022*

	U11	U22	U33	U12	U13	U23
S1	0.01993 (17)	0.01434 (16)	0.01670 (17)	0.00078 (11)	−0.00157 (12)	0.00075 (10)
C2	0.0163 (6)	0.0159 (6)	0.0173 (6)	−0.0001 (5)	0.0017 (5)	0.0013 (5)
N3	0.0218 (6)	0.0165 (6)	0.0194 (5)	0.0011 (4)	−0.0001 (4)	0.0017 (4)
C3A	0.0190 (6)	0.0186 (7)	0.0192 (6)	0.0002 (5)	0.0017 (5)	0.0028 (5)
C4	0.0278 (7)	0.0171 (7)	0.0240 (7)	0.0003 (5)	0.0005 (6)	0.0008 (5)
C5	0.0277 (7)	0.0180 (7)	0.0284 (7)	0.0024 (5)	0.0022 (6)	0.0072 (6)
C6	0.0237 (7)	0.0235 (7)	0.0222 (7)	0.0015 (5)	−0.0001 (5)	0.0076 (5)
C7	0.0205 (7)	0.0224 (7)	0.0192 (6)	0.0001 (5)	−0.0002 (5)	0.0018 (5)
C7A	0.0161 (6)	0.0164 (6)	0.0209 (6)	0.0011 (5)	0.0021 (5)	0.0023 (5)
S2	0.0467 (2)	0.01438 (18)	0.02184 (19)	−0.00151 (14)	−0.01103 (15)	0.00050 (12)
N1	0.0206 (6)	0.0145 (5)	0.0159 (5)	0.0002 (4)	−0.0023 (4)	0.0008 (4)
N2	0.0224 (6)	0.0122 (5)	0.0183 (5)	0.0002 (4)	−0.0014 (4)	0.0016 (4)
N4	0.0201 (6)	0.0226 (6)	0.0206 (6)	−0.0019 (4)	−0.0025 (4)	0.0037 (5)
O1	0.0314 (5)	0.0138 (4)	0.0214 (5)	0.0004 (4)	−0.0037 (4)	0.0006 (4)
O2	0.0372 (6)	0.0211 (5)	0.0294 (6)	0.0048 (4)	−0.0073 (5)	0.0060 (4)
O3	0.0439 (7)	0.0301 (6)	0.0182 (5)	−0.0027 (5)	−0.0059 (4)	−0.0006 (4)
C8	0.0190 (6)	0.0174 (6)	0.0182 (6)	0.0002 (5)	0.0012 (5)	0.0023 (5)
C9	0.0177 (6)	0.0168 (6)	0.0179 (6)	0.0006 (5)	0.0027 (5)	0.0000 (5)
C10	0.0156 (6)	0.0162 (6)	0.0186 (6)	−0.0008 (5)	0.0019 (5)	0.0008 (5)
C11	0.0220 (7)	0.0160 (6)	0.0190 (6)	−0.0003 (5)	−0.0024 (5)	−0.0019 (5)
C12	0.0215 (6)	0.0149 (6)	0.0227 (7)	0.0008 (5)	−0.0015 (5)	0.0002 (5)
C13	0.0162 (6)	0.0194 (6)	0.0168 (6)	0.0001 (5)	−0.0007 (5)	0.0026 (5)
C14	0.0191 (6)	0.0194 (6)	0.0178 (6)	−0.0012 (5)	0.0011 (5)	−0.0018 (5)
C15	0.0204 (6)	0.0143 (6)	0.0210 (7)	−0.0006 (5)	0.0015 (5)	−0.0005 (5)

S1—C7A	1.7443 (13)	O1—C9	1.2269 (16)
S1—C2	1.7529 (13)	C9—C10	1.4927 (18)
C2—N3	1.2994 (18)	C10—C11	1.3949 (19)
C2—N1	1.3877 (17)	C10—C15	1.4017 (19)
N3—C3A	1.3896 (17)	C11—C12	1.3890 (18)
C3A—C4	1.4002 (19)	C12—C13	1.3815 (19)
C3A—C7A	1.4009 (19)	C13—C14	1.3863 (19)
C4—C5	1.383 (2)	C14—C15	1.3828 (19)
C5—C6	1.403 (2)	C4—H4	0.9500
C6—C7	1.385 (2)	C5—H5	0.9500
C7—C7A	1.3982 (18)	C6—H6	0.9500
S2—C8	1.6439 (14)	C7—H7	0.9500
N1—C8	1.3499 (17)	N1—H01	0.832 (19)
N2—C9	1.3791 (17)	N2—H02	0.84 (2)
N2—C8	1.4007 (17)	C11—H11	0.9500
N4—O3	1.2246 (16)	C12—H12	0.9500
N4—O2	1.2264 (16)	C14—H14	0.9500
N4—C13	1.4731 (16)	C15—H15	0.9500
C7A—S1—C2	87.52 (6)	C15—C10—C9	116.03 (11)
N3—C2—N1	117.86 (12)	C12—C11—C10	120.24 (12)
N3—C2—S1	117.58 (10)	C13—C12—C11	118.26 (12)
N1—C2—S1	124.55 (10)	C12—C13—C14	122.94 (12)
C2—N3—C3A	109.55 (11)	C12—C13—N4	118.49 (12)
N3—C3A—C4	125.00 (13)	C14—C13—N4	118.56 (12)
N3—C3A—C7A	115.09 (12)	C15—C14—C13	118.37 (12)
C4—C3A—C7A	119.89 (12)	C14—C15—C10	120.15 (12)
C5—C4—C3A	118.59 (13)	C5—C4—H4	120.7
C4—C5—C6	121.06 (13)	C3A—C4—H4	120.7
C7—C6—C5	121.08 (13)	C4—C5—H5	119.5
C6—C7—C7A	117.75 (13)	C6—C5—H5	119.5
C7—C7A—C3A	121.62 (12)	C7—C6—H6	119.5
C7—C7A—S1	128.12 (11)	C5—C6—H6	119.5
C3A—C7A—S1	110.23 (10)	C6—C7—H7	121.1
C8—N1—C2	128.62 (12)	C7A—C7—H7	121.1
C9—N2—C8	127.82 (11)	C8—N1—H01	117.8 (13)
O3—N4—O2	124.13 (12)	C2—N1—H01	113.5 (13)
O3—N4—C13	118.13 (11)	C9—N2—H02	121.6 (13)
O2—N4—C13	117.74 (11)	C8—N2—H02	110.6 (13)
N1—C8—N2	114.50 (12)	C12—C11—H11	119.9
N1—C8—S2	124.95 (10)	C10—C11—H11	119.9
N2—C8—S2	120.54 (10)	C13—C12—H12	120.9
O1—C9—N2	122.03 (12)	C11—C12—H12	120.9
O1—C9—C10	120.50 (12)	C15—C14—H14	120.8
N2—C9—C10	117.47 (11)	C13—C14—H14	120.8
C11—C10—C15	120.00 (12)	C14—C15—H15	119.9
C11—C10—C9	123.96 (12)	C10—C15—H15	119.9
C7A—S1—C2—N3	−1.03 (11)	C9—N2—C8—N1	7.7 (2)
C7A—S1—C2—N1	177.99 (12)	C9—N2—C8—S2	−173.54 (11)
N1—C2—N3—C3A	−178.55 (11)	C8—N2—C9—O1	−1.8 (2)
S1—C2—N3—C3A	0.54 (15)	C8—N2—C9—C10	178.80 (12)
C2—N3—C3A—C4	−178.51 (13)	O1—C9—C10—C11	169.88 (13)
C2—N3—C3A—C7A	0.44 (16)	N2—C9—C10—C11	−10.69 (19)
N3—C3A—C4—C5	179.12 (13)	O1—C9—C10—C15	−10.64 (19)
C7A—C3A—C4—C5	0.2 (2)	N2—C9—C10—C15	168.79 (12)
C3A—C4—C5—C6	0.3 (2)	C15—C10—C11—C12	−1.0 (2)
C4—C5—C6—C7	−0.6 (2)	C9—C10—C11—C12	178.44 (12)
C5—C6—C7—C7A	0.5 (2)	C10—C11—C12—C13	−0.5 (2)
C6—C7—C7A—C3A	0.0 (2)	C11—C12—C13—C14	1.8 (2)
C6—C7—C7A—S1	−177.83 (11)	C11—C12—C13—N4	−176.88 (12)
N3—C3A—C7A—C7	−179.35 (12)	O3—N4—C13—C12	169.77 (12)
C4—C3A—C7A—C7	−0.3 (2)	O2—N4—C13—C12	−9.23 (19)
N3—C3A—C7A—S1	−1.19 (15)	O3—N4—C13—C14	−8.94 (19)
C4—C3A—C7A—S1	177.82 (11)	O2—N4—C13—C14	172.05 (12)
C2—S1—C7A—C7	179.17 (13)	C12—C13—C14—C15	−1.4 (2)
C2—S1—C7A—C3A	1.17 (10)	N4—C13—C14—C15	177.23 (12)
N3—C2—N1—C8	−175.86 (13)	C13—C14—C15—C10	−0.2 (2)
S1—C2—N1—C8	5.1 (2)	C11—C10—C15—C14	1.4 (2)
C2—N1—C8—N2	−179.42 (12)	C9—C10—C15—C14	−178.12 (12)
C2—N1—C8—S2	1.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H01···O1	0.83 (2)	1.92 (2)	2.598 (2)	138 (2)
N2—H02···O2i	0.84 (2)	2.42 (2)	3.261 (2)	175 (2)
C5—H5···O1ii	0.95	2.55	3.462 (2)	161
C11—H11···O2i	0.95	2.41	3.318 (2)	159
C12—H12···S2iii	0.95	2.73	3.673 (1)	173
C7—H7···S2iv	0.95	2.91	3.563 (1)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H01⋯O1	0.83 (2)	1.92 (2)	2.598 (2)	138 (2)
N2—H02⋯O2i	0.84 (2)	2.42 (2)	3.261 (2)	175 (2)
C5—H5⋯O1ii	0.95	2.55	3.462 (2)	161
C11—H11⋯O2i	0.95	2.41	3.318 (2)	159
C12—H12⋯S2iii	0.95	2.73	3.673 (1)	173
C7—H7⋯S2iv	0.95	2.91	3.563 (1)	127

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .