N-(3-Nitro-phen-yl)-N'-pivaloylthio-urea.

In the title compound, C(12)H(15)N(3)O(3)S, there is an intra-molecular N-H⋯O hydrogen bond. The crystal structure is stabilized by inter-molecular N-H⋯O, N-H⋯S and C-H⋯S hydrogen bonds, forming a two-dimensional network parallel to the ac plane.

Related literature

For related crystal structures, see: Saeed & Flörke (2007 ▶); Sultana et al. (2007 ▶).

Experimental

Crystal data

C12H15N3O3S

M = 281.33

Orthorhombic,

a = 20.400 (5) Å

b = 10.886 (3) Å

c = 6.2120 (15) Å

V = 1379.5 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 273 (2) K

0.48 × 0.18 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.893, T max = 0.972

8152 measured reflections

3020 independent reflections

2321 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.103

S = 0.91

3020 reflections

172 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.14 e Å−3

Absolute structure: Flack (1983 ▶), 1296 Friedel pairs

Flack parameter: 0.07 (9)

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808014530/sg2240sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014530/sg2240Isup2.hkl

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

C12H15N3O3S	F000 = 592
Mr = 281.33	Dx = 1.355 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 925 reflections
a = 20.400 (5) Å	θ = 2.0–27.5º
b = 10.886 (3) Å	µ = 0.24 mm−1
c = 6.2120 (15) Å	T = 273 (2) K
V = 1379.5 (6) Å3	Block, colourless
Z = 4	0.48 × 0.18 × 0.12 mm

Bruker SMART APEX CCD area-detector diffractometer	3020 independent reflections
Radiation source: fine-focus sealed tube	2321 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.032
Detector resolution: 83.66 pixels mm-1	θmax = 27.5º
T = 298(2) K	θmin = 2.0º
ω scans	h = −21→26
Absorption correction: multi-scan(SADABS; Bruker, 2000)	k = −13→14
Tmin = 0.893, Tmax = 0.972	l = −7→7
8152 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.042	w = 1/[σ2(Fo2) + (0.0642P)2 + 0.0515P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.103	(Δ/σ)max < 0.001
S = 0.91	Δρmax = 0.28 e Å−3
3020 reflections	Δρmin = −0.14 e Å−3
172 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), 1296 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.07 (9)
Secondary atom site location: difference Fourier map

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	0.97040 (3)	0.39600 (5)	0.62603 (13)	0.04412 (17)
O3	0.72971 (13)	0.0240 (2)	0.9230 (4)	0.0936 (8)
O2	0.73374 (10)	0.13216 (17)	0.6346 (5)	0.0791 (6)
O1	0.84682 (10)	0.73243 (15)	0.7556 (4)	0.0694 (6)
N2	0.86872 (9)	0.49974 (16)	0.8218 (3)	0.0422 (5)
H2A	0.8456	0.5640	0.8480	0.051*
N1	0.92866 (9)	0.62483 (14)	0.5965 (3)	0.0394 (5)
H1A	0.9603	0.6304	0.5055	0.047*
C11	0.79218 (11)	0.2008 (2)	0.9299 (4)	0.0414 (5)
C10	0.81336 (11)	0.1747 (2)	1.1350 (5)	0.0490 (6)
H10A	0.7999	0.1035	1.2052	0.059*
C9	0.85486 (13)	0.2563 (2)	1.2331 (5)	0.0521 (6)
H9A	0.8704	0.2395	1.3708	0.062*
C8	0.87392 (11)	0.36328 (19)	1.1304 (5)	0.0463 (5)
H8A	0.9018	0.4187	1.1985	0.056*
C7	0.85101 (11)	0.38661 (19)	0.9253 (4)	0.0387 (5)
C12	0.80979 (11)	0.3062 (2)	0.8226 (4)	0.0413 (5)
H12A	0.7942	0.3224	0.6848	0.050*
N3	0.74809 (11)	0.11334 (19)	0.8218 (5)	0.0557 (6)
C6	0.91904 (11)	0.50999 (19)	0.6876 (4)	0.0375 (5)
C5	0.89385 (11)	0.73105 (18)	0.6338 (5)	0.0421 (5)
C4	0.91691 (13)	0.8460 (2)	0.5166 (4)	0.0451 (6)
C3	0.90038 (15)	0.8322 (3)	0.2772 (5)	0.0635 (8)
H3A	0.9239	0.7634	0.2189	0.095*
H3B	0.9128	0.9056	0.2019	0.095*
H3C	0.8541	0.8188	0.2610	0.095*
C2	0.87985 (15)	0.9559 (2)	0.6113 (7)	0.0733 (8)
H2B	0.8905	0.9641	0.7611	0.110*
H2C	0.8335	0.9430	0.5958	0.110*
H2D	0.8923	1.0294	0.5363	0.110*
C1	0.99039 (14)	0.8627 (2)	0.5451 (6)	0.0625 (8)
H1B	1.0130	0.7938	0.4834	0.094*
H1C	1.0005	0.8681	0.6957	0.094*
H1D	1.0041	0.9368	0.4742	0.094*

	U11	U22	U33	U12	U13	U23
S1	0.0528 (3)	0.0349 (3)	0.0446 (3)	0.0050 (2)	0.0020 (3)	0.0025 (3)
O3	0.124 (2)	0.0680 (13)	0.0885 (16)	−0.0522 (13)	0.0132 (15)	−0.0002 (13)
O2	0.0909 (15)	0.0660 (12)	0.0804 (15)	−0.0173 (10)	−0.0336 (15)	0.0052 (14)
O1	0.0707 (13)	0.0443 (10)	0.0930 (16)	0.0126 (9)	0.0308 (12)	0.0156 (10)
N2	0.0457 (10)	0.0311 (9)	0.0497 (11)	0.0041 (8)	0.0075 (10)	0.0086 (8)
N1	0.0440 (10)	0.0325 (9)	0.0416 (13)	−0.0003 (7)	0.0044 (10)	0.0064 (8)
C11	0.0378 (12)	0.0376 (12)	0.0488 (14)	−0.0003 (10)	0.0062 (11)	0.0013 (11)
C10	0.0557 (14)	0.0387 (11)	0.0526 (14)	−0.0019 (10)	0.0128 (15)	0.0136 (15)
C9	0.0650 (16)	0.0508 (14)	0.0404 (13)	0.0030 (13)	−0.0015 (12)	0.0109 (12)
C8	0.0488 (12)	0.0427 (11)	0.0474 (13)	−0.0016 (9)	−0.0003 (15)	−0.0004 (14)
C7	0.0396 (13)	0.0366 (12)	0.0399 (13)	0.0020 (9)	0.0051 (10)	0.0043 (10)
C12	0.0423 (13)	0.0409 (12)	0.0409 (13)	0.0024 (10)	0.0016 (11)	0.0056 (11)
N3	0.0540 (13)	0.0435 (12)	0.0695 (16)	−0.0055 (10)	0.0068 (12)	−0.0009 (11)
C6	0.0391 (11)	0.0367 (12)	0.0366 (14)	−0.0034 (10)	−0.0084 (9)	0.0029 (9)
C5	0.0441 (12)	0.0350 (10)	0.0471 (12)	0.0004 (9)	0.0006 (13)	0.0067 (13)
C4	0.0520 (15)	0.0313 (11)	0.0519 (15)	−0.0003 (11)	0.0008 (12)	0.0078 (10)
C3	0.0761 (19)	0.0570 (16)	0.0575 (19)	−0.0034 (14)	−0.0070 (15)	0.0183 (14)
C2	0.093 (2)	0.0359 (12)	0.091 (2)	0.0162 (13)	0.020 (2)	0.0097 (18)
C1	0.0643 (18)	0.0414 (14)	0.082 (2)	−0.0118 (13)	−0.0026 (15)	0.0018 (13)

S1—C6	1.668 (2)	C8—C7	1.381 (4)
O3—N3	1.217 (3)	C8—H8A	0.9300
O2—N3	1.216 (3)	C7—C12	1.371 (3)
O1—C5	1.222 (3)	C12—H12A	0.9300
N2—C6	1.327 (3)	C5—C4	1.523 (3)
N2—C7	1.435 (3)	C4—C1	1.520 (4)
N2—H2A	0.8600	C4—C3	1.532 (4)
N1—C5	1.377 (3)	C4—C2	1.532 (4)
N1—C6	1.386 (3)	C3—H3A	0.9600
N1—H1A	0.8600	C3—H3B	0.9600
C11—C10	1.375 (4)	C3—H3C	0.9600
C11—C12	1.375 (3)	C2—H2B	0.9600
C11—N3	1.472 (3)	C2—H2C	0.9600
C10—C9	1.370 (4)	C2—H2D	0.9600
C10—H10A	0.9300	C1—H1B	0.9600
C9—C8	1.384 (3)	C1—H1C	0.9600
C9—H9A	0.9300	C1—H1D	0.9600
C6—N2—C7	123.23 (18)	N1—C6—S1	119.22 (17)
C6—N2—H2A	118.4	O1—C5—N1	121.3 (2)
C7—N2—H2A	118.4	O1—C5—C4	121.9 (2)
C5—N1—C6	128.0 (2)	N1—C5—C4	116.8 (2)
C5—N1—H1A	116.0	C1—C4—C5	110.3 (2)
C6—N1—H1A	116.0	C1—C4—C3	110.0 (2)
C10—C11—C12	122.7 (2)	C5—C4—C3	108.4 (2)
C10—C11—N3	118.8 (2)	C1—C4—C2	110.4 (2)
C12—C11—N3	118.6 (2)	C5—C4—C2	107.8 (2)
C9—C10—C11	118.2 (2)	C3—C4—C2	109.9 (3)
C9—C10—H10A	120.9	C4—C3—H3A	109.5
C11—C10—H10A	120.9	C4—C3—H3B	109.5
C10—C9—C8	120.9 (3)	H3A—C3—H3B	109.5
C10—C9—H9A	119.5	C4—C3—H3C	109.5
C8—C9—H9A	119.5	H3A—C3—H3C	109.5
C7—C8—C9	119.0 (2)	H3B—C3—H3C	109.5
C7—C8—H8A	120.5	C4—C2—H2B	109.5
C9—C8—H8A	120.5	C4—C2—H2C	109.5
C12—C7—C8	121.3 (2)	H2B—C2—H2C	109.5
C12—C7—N2	119.6 (2)	C4—C2—H2D	109.5
C8—C7—N2	119.1 (2)	H2B—C2—H2D	109.5
C7—C12—C11	117.9 (2)	H2C—C2—H2D	109.5
C7—C12—H12A	121.1	C4—C1—H1B	109.5
C11—C12—H12A	121.1	C4—C1—H1C	109.5
O2—N3—O3	123.7 (3)	H1B—C1—H1C	109.5
O2—N3—C11	118.3 (2)	C4—C1—H1D	109.5
O3—N3—C11	118.0 (3)	H1B—C1—H1D	109.5
N2—C6—N1	116.21 (19)	H1C—C1—H1D	109.5
N2—C6—S1	124.57 (17)
C12—C11—C10—C9	−1.5 (4)	C10—C11—N3—O3	3.4 (3)
N3—C11—C10—C9	179.4 (2)	C12—C11—N3—O3	−175.7 (2)
C11—C10—C9—C8	1.2 (4)	C7—N2—C6—N1	178.4 (2)
C10—C9—C8—C7	−0.6 (4)	C7—N2—C6—S1	−2.2 (3)
C9—C8—C7—C12	0.2 (4)	C5—N1—C6—N2	2.6 (4)
C9—C8—C7—N2	177.6 (2)	C5—N1—C6—S1	−176.9 (2)
C6—N2—C7—C12	−87.3 (3)	C6—N1—C5—O1	−2.1 (4)
C6—N2—C7—C8	95.2 (3)	C6—N1—C5—C4	177.8 (2)
C8—C7—C12—C11	−0.4 (3)	O1—C5—C4—C1	130.5 (3)
N2—C7—C12—C11	−177.81 (19)	N1—C5—C4—C1	−49.4 (3)
C10—C11—C12—C7	1.0 (3)	O1—C5—C4—C3	−109.0 (3)
N3—C11—C12—C7	−179.9 (2)	N1—C5—C4—C3	71.1 (3)
C10—C11—N3—O2	−174.3 (2)	O1—C5—C4—C2	9.9 (4)
C12—C11—N3—O2	6.6 (3)	N1—C5—C4—C2	−170.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.92	2.605 (3)	135
N1—H1A···S1i	0.86	2.76	3.582 (2)	160
C3—H3A···S1i	0.96	2.83	3.742 (3)	159
N2—H2A···O2ii	0.86	2.52	3.197 (3)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.86	1.92	2.605 (3)	135
N1—H1A⋯S1i	0.86	2.76	3.582 (2)	160
C3—H3A⋯S1i	0.96	2.83	3.742 (3)	159
N2—H2A⋯O2ii	0.86	2.52	3.197 (3)	137

Symmetry codes: (i) ; (ii) .