(E)-O-Isopropyl N-(4-nitro-phen-yl)thio-carbamate.

The configuration of the thione-aryl C-N single bond in the title mol-ecule, C(10)H(12)N(2)O(3)S, is E. Centrosymmetrically related mol-ecules are connected into a dimer via an eight-membered thio-amide {⋯H-N-C=S}(2) synthon and mol-ecules are consolidated into the crystal structure via C-H⋯O inter-actions.

Related literature

For related structures, see: Ho et al. (2005 ▶); Kuan et al. (2007 ▶). For related literature, see: Ho et al. (2006 ▶); Ho & Tiekink (2007 ▶).

Experimental

Crystal data

C10H12N2O3S

M = 240.28

Triclinic,

a = 7.4200 (8) Å

b = 8.3206 (9) Å

c = 10.0993 (11) Å

α = 111.414 (4)°

β = 97.877 (5)°

γ = 94.130 (5)°

V = 569.94 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.28 mm−1

T = 98 (2) K

0.30 × 0.18 × 0.10 mm

Data collection

Rigaku AFC12κ/SATURN724 diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.915, T max = 1 (expected range = 0.890–0.973)

3875 measured reflections

2221 independent reflections

2103 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.119

S = 1.33

2221 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: TwinSolve (Rigaku and Prekat AB, 2006 ▶); data reduction: TwinSolve; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶) and n class="Disease">DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807067360/ng2410sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807067360/ng2410Isup2.hkl

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

C10H12N2O3S	Z = 2
Mr = 240.28	F000 = 252
Triclinic, P1	Dx = 1.400 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71070 Å
a = 7.4200 (8) Å	Cell parameters from 4435 reflections
b = 8.3206 (9) Å	θ = 2.6–29.2º
c = 10.0993 (11) Å	µ = 0.28 mm−1
α = 111.414 (4)º	T = 98 (2) K
β = 97.877 (5)º	Block, yellow
γ = 94.130 (5)º	0.30 × 0.18 × 0.10 mm
V = 569.94 (11) Å3

Rigaku AFC12κ/SATURN724 diffractometer	2221 independent reflections
Radiation source: fine-focus sealed tube	2103 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.024
T = 98(2) K	θmax = 26.0º
ω scans	θmin = 2.7º
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)	h = −9→9
Tmin = 0.915, Tmax = 1	k = −10→10
3875 measured reflections	l = −12→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066	H-atom parameters constrained
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0191P)2 + 0.7747P] where P = (Fo2 + 2Fc2)/3
S = 1.33	(Δ/σ)max < 0.001
2221 reflections	Δρmax = 0.29 e Å−3
145 parameters	Δρmin = −0.24 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.55527 (11)	0.09264 (11)	0.23408 (8)	0.0271 (2)
O1	0.2493 (3)	0.2303 (3)	0.3002 (2)	0.0227 (4)
O2	−0.4727 (3)	0.3762 (3)	−0.1315 (2)	0.0369 (6)
O3	−0.3181 (3)	0.3892 (3)	−0.2947 (2)	0.0391 (6)
N1	0.2838 (3)	0.1543 (3)	0.0701 (2)	0.0238 (5)
H1N	0.3503	0.1049	0.0042	0.029*
N2	−0.3330 (3)	0.3620 (3)	−0.1846 (3)	0.0268 (6)
C1	0.3532 (4)	0.1629 (4)	0.2037 (3)	0.0215 (6)
C2	0.1242 (4)	0.2101 (4)	0.0165 (3)	0.0216 (6)
C3	−0.0289 (4)	0.2438 (4)	0.0835 (3)	0.0247 (6)
H3	−0.0301	0.2328	0.1737	0.030*
C4	−0.1797 (4)	0.2937 (4)	0.0174 (3)	0.0241 (6)
H4	−0.2850	0.3168	0.0618	0.029*
C5	−0.1743 (4)	0.3091 (4)	−0.1142 (3)	0.0218 (6)
C6	−0.0249 (4)	0.2768 (4)	−0.1820 (3)	0.0255 (6)
H6	−0.0240	0.2889	−0.2719	0.031*
C7	0.1240 (4)	0.2261 (4)	−0.1162 (3)	0.0256 (6)
H7	0.2279	0.2018	−0.1621	0.031*
C8	0.3146 (4)	0.2614 (4)	0.4537 (3)	0.0244 (6)
H8	0.4509	0.2935	0.4777	0.029*
C9	0.2226 (5)	0.4141 (4)	0.5385 (3)	0.0306 (7)
H9A	0.2637	0.5168	0.5193	0.046*
H9B	0.2557	0.4388	0.6419	0.046*
H9C	0.0891	0.3852	0.5088	0.046*
C10	0.2626 (5)	0.0986 (4)	0.4801 (3)	0.0331 (7)
H10A	0.3280	0.0054	0.4248	0.050*
H10B	0.1300	0.0627	0.4494	0.050*
H10C	0.2962	0.1218	0.5833	0.050*

	U11	U22	U33	U12	U13	U23
S1	0.0270 (4)	0.0355 (4)	0.0209 (4)	0.0135 (3)	0.0040 (3)	0.0115 (3)
O1	0.0240 (10)	0.0282 (11)	0.0172 (10)	0.0079 (8)	0.0036 (8)	0.0095 (8)
O2	0.0287 (12)	0.0482 (15)	0.0355 (13)	0.0145 (11)	0.0051 (10)	0.0161 (11)
O3	0.0336 (13)	0.0576 (16)	0.0340 (13)	0.0068 (11)	−0.0020 (10)	0.0294 (12)
N1	0.0260 (13)	0.0285 (13)	0.0176 (12)	0.0101 (10)	0.0044 (10)	0.0083 (10)
N2	0.0272 (14)	0.0238 (13)	0.0262 (13)	0.0006 (10)	−0.0026 (11)	0.0089 (11)
C1	0.0269 (15)	0.0216 (14)	0.0161 (13)	0.0057 (12)	0.0023 (11)	0.0072 (11)
C2	0.0229 (14)	0.0199 (14)	0.0184 (14)	0.0013 (11)	−0.0002 (11)	0.0049 (11)
C3	0.0262 (15)	0.0313 (16)	0.0191 (14)	0.0066 (12)	0.0029 (11)	0.0125 (12)
C4	0.0235 (15)	0.0253 (15)	0.0238 (15)	0.0058 (12)	0.0072 (12)	0.0082 (12)
C5	0.0233 (14)	0.0183 (14)	0.0209 (14)	0.0007 (11)	−0.0039 (11)	0.0071 (11)
C6	0.0303 (16)	0.0275 (16)	0.0190 (14)	0.0029 (12)	0.0032 (12)	0.0097 (12)
C7	0.0234 (15)	0.0310 (16)	0.0228 (15)	0.0062 (12)	0.0056 (12)	0.0098 (13)
C8	0.0256 (15)	0.0311 (16)	0.0175 (14)	0.0065 (12)	0.0014 (11)	0.0109 (12)
C9	0.0358 (17)	0.0305 (17)	0.0258 (16)	0.0099 (14)	0.0080 (13)	0.0093 (13)
C10	0.0429 (19)	0.0363 (18)	0.0262 (16)	0.0100 (15)	0.0087 (14)	0.0171 (14)

S1—C1	1.678 (3)	C4—H4	0.9500
O1—C1	1.314 (3)	C5—C6	1.373 (4)
O1—C8	1.479 (3)	C6—C7	1.383 (4)
O2—N2	1.224 (3)	C6—H6	0.9500
O3—N2	1.231 (3)	C7—H7	0.9500
N1—C1	1.352 (3)	C8—C10	1.508 (4)
N1—C2	1.413 (4)	C8—C9	1.517 (4)
N1—H1N	0.8800	C8—H8	1.0000
N2—C5	1.470 (4)	C9—H9A	0.9800
C2—C7	1.394 (4)	C9—H9B	0.9800
C2—C3	1.395 (4)	C9—H9C	0.9800
C3—C4	1.391 (4)	C10—H10A	0.9800
C3—H3	0.9500	C10—H10B	0.9800
C4—C5	1.387 (4)	C10—H10C	0.9800
C1—O1—C8	119.8 (2)	C5—C6—H6	120.9
C1—N1—C2	131.9 (2)	C7—C6—H6	120.9
C1—N1—H1N	114.0	C6—C7—C2	121.1 (3)
C2—N1—H1N	114.0	C6—C7—H7	119.4
O2—N2—O3	123.5 (3)	C2—C7—H7	119.4
O2—N2—C5	118.7 (2)	O1—C8—C10	109.3 (2)
O3—N2—C5	117.8 (2)	O1—C8—C9	105.0 (2)
O1—C1—N1	113.7 (2)	C10—C8—C9	112.9 (3)
O1—C1—S1	126.2 (2)	O1—C8—H8	109.8
N1—C1—S1	120.2 (2)	C10—C8—H8	109.8
C7—C2—C3	119.6 (3)	C9—C8—H8	109.8
C7—C2—N1	115.1 (3)	C8—C9—H9A	109.5
C3—C2—N1	125.2 (3)	C8—C9—H9B	109.5
C4—C3—C2	119.6 (3)	H9A—C9—H9B	109.5
C4—C3—H3	120.2	C8—C9—H9C	109.5
C2—C3—H3	120.2	H9A—C9—H9C	109.5
C5—C4—C3	119.0 (3)	H9B—C9—H9C	109.5
C5—C4—H4	120.5	C8—C10—H10A	109.5
C3—C4—H4	120.5	C8—C10—H10B	109.5
C6—C5—C4	122.4 (3)	H10A—C10—H10B	109.5
C6—C5—N2	118.3 (3)	C8—C10—H10C	109.5
C4—C5—N2	119.4 (3)	H10A—C10—H10C	109.5
C5—C6—C7	118.2 (3)	H10B—C10—H10C	109.5
C8—O1—C1—N1	−175.0 (2)	O2—N2—C5—C6	173.7 (3)
C8—O1—C1—S1	4.4 (4)	O3—N2—C5—C6	−6.1 (4)
C2—N1—C1—O1	2.6 (4)	O2—N2—C5—C4	−6.4 (4)
C2—N1—C1—S1	−176.8 (3)	O3—N2—C5—C4	173.8 (3)
C1—N1—C2—C7	162.0 (3)	C4—C5—C6—C7	0.4 (4)
C1—N1—C2—C3	−19.9 (5)	N2—C5—C6—C7	−179.7 (3)
C7—C2—C3—C4	−0.2 (4)	C5—C6—C7—C2	−0.8 (4)
N1—C2—C3—C4	−178.3 (3)	C3—C2—C7—C6	0.7 (4)
C2—C3—C4—C5	−0.1 (4)	N1—C2—C7—C6	178.9 (3)
C3—C4—C5—C6	0.0 (4)	C1—O1—C8—C10	−87.1 (3)
C3—C4—C5—N2	−179.9 (3)	C1—O1—C8—C9	151.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···S1i	0.88	2.59	3.440 (2)	162
C7—H7···O2ii	0.95	2.48	3.204 (4)	133
C8—H8···O3iii	1.00	2.50	3.275 (4)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯S1i	0.88	2.59	3.440 (2)	162
C7—H7⋯O2ii	0.95	2.48	3.204 (4)	133
C8—H8⋯O3iii	1.00	2.50	3.275 (4)	134

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