4-Nitro-phenyl N-(2-isopropyl-thia-zol-4-ylmeth-yl)-N-methyl-carbamate.

In the title compound, C(15)H(17)N(3)O(4)S, the benzene and thia-zole rings are oriented at a dihedral angle of 74.10 (3)°. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds are found.

Related literature

For related literature, see: Allen et al. (1987 ▶); Ishikawa et al. (1998 ▶); Riden & Hopkins (1961 ▶).

Experimental

Crystal data

C15H17N3O4S

M = 335.38

Orthorhombic,

a = 12.250 (3) Å

b = 10.876 (2) Å

c = 24.845 (5) Å

V = 3310.1 (12) Å3

Z = 8

Mo Kα radiation

μ = 0.22 mm−1

T = 298 (2) K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.937, T max = 0.979

3281 measured reflections

3241 independent reflections

1335 reflections with I > 2σ(I)

R int = 0.072

3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.086

wR(F 2) = 0.217

S = 1.04

3241 reflections

184 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.39 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Siemens,1996 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807063532/bq2046sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063532/bq2046Isup2.hkl

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

C15H17N3O4S	Dx = 1.346 Mg m−3
Mr = 335.38	Melting point: 330(2) K
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 12.250 (3) Å	θ = 9–12º
b = 10.876 (2) Å	µ = 0.22 mm−1
c = 24.845 (5) Å	T = 298 (2) K
V = 3310.1 (12) Å3	Block, colourless
Z = 8	0.30 × 0.20 × 0.10 mm
F000 = 1408

Enraf–Nonius CAD-4 diffractometer	Rint = 0.072
Radiation source: fine-focus sealed tube	θmax = 26.0º
Monochromator: graphite	θmin = 1.6º
T = 298(2) K	h = 0→15
ω/2θ scans	k = 0→13
Absorption correction: ψ scan(North et al., 1968)	l = 0→30
Tmin = 0.937, Tmax = 0.979	3 standard reflections
3281 measured reflections	every 200 reflections
3241 independent reflections	intensity decay: none
1335 reflections with I > 2σ(I)

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)] = 0.086	H-atom parameters constrained
wR(F2) = 0.217	w = 1/[σ2(Fo2) + (0.070P)2 + 2.P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3241 reflections	Δρmax = 0.28 e Å−3
184 parameters	Δρmin = −0.39 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
S	0.33658 (15)	0.04646 (16)	0.50156 (7)	0.089
N2	0.2887 (3)	−0.0166 (3)	0.68311 (16)	0.0430 (10)
O1	0.1531 (3)	−0.1308 (3)	0.71949 (15)	0.0610 (10)
C1	0.5582 (5)	0.2987 (6)	0.4986 (2)	0.084
H1A	0.5915	0.2283	0.5152	0.127*
H1B	0.5618	0.3675	0.5227	0.127*
H1C	0.5963	0.3182	0.4659	0.127*
O2	0.1198 (2)	0.0537 (3)	0.68088 (16)	0.0585 (10)
N3	−0.3347 (4)	0.0160 (5)	0.6666 (2)	0.0668 (14)
C2	0.3731 (4)	0.3175 (5)	0.4459 (2)	0.072
H2A	0.4102	0.3809	0.4262	0.108*
H2B	0.3087	0.3510	0.4623	0.108*
H2C	0.3529	0.2523	0.4218	0.108*
O3	−0.3851 (3)	0.1042 (4)	0.6861 (2)	0.1009 (16)
C3	0.4429 (5)	0.2710 (6)	0.4862 (3)	0.100 (2)
H3A	0.4661	0.2049	0.4619	0.120*
O4	−0.3738 (3)	−0.0692 (5)	0.6433 (2)	0.1038 (17)
C4	0.3950 (5)	0.1777 (6)	0.5238 (3)	0.0841 (19)
N1	0.3889 (4)	0.1941 (5)	0.5758 (2)	0.0771 (14)
C5	0.3383 (4)	0.0953 (4)	0.6001 (2)	0.0504 (13)
C6	0.3035 (5)	0.0073 (6)	0.5665 (2)	0.0785 (17)
H6A	0.2670	−0.0640	0.5767	0.094*
C7	0.3260 (4)	0.0983 (4)	0.6607 (2)	0.0491 (13)
H7A	0.3959	0.1191	0.6767	0.059*
H7B	0.2746	0.1625	0.6703	0.059*
C8	0.3718 (3)	−0.1137 (4)	0.6951 (2)	0.0547 (15)
H8A	0.3359	−0.1851	0.7094	0.082*
H8B	0.4231	−0.0830	0.7210	0.082*
H8C	0.4096	−0.1353	0.6626	0.082*
C9	0.1861 (4)	−0.0440 (5)	0.69588 (18)	0.0460 (12)
C10	0.0078 (3)	0.0370 (4)	0.6816 (2)	0.0448 (12)
C11	−0.0386 (4)	−0.0625 (4)	0.6552 (2)	0.0494 (12)
H11A	0.0058	−0.1238	0.6409	0.059*
C12	−0.1534 (4)	−0.0707 (5)	0.6500 (2)	0.0564 (13)
H12A	−0.1871	−0.1356	0.6322	0.068*
C13	−0.2133 (3)	0.0258 (5)	0.67368 (19)	0.0457 (12)
C14	−0.1691 (4)	0.1211 (4)	0.6979 (2)	0.0483 (12)
H14A	−0.2127	0.1839	0.7113	0.058*
C15	−0.0556 (3)	0.1265 (4)	0.70306 (18)	0.041
H15A	−0.0235	0.1918	0.7213	0.049*

	U11	U22	U33	U12	U13	U23
S	0.089	0.089	0.089	0.000	0.000	0.000
N2	0.035 (2)	0.035 (2)	0.059 (3)	0.0008 (17)	−0.0029 (19)	0.009 (2)
O1	0.059 (2)	0.044 (2)	0.080 (3)	−0.0118 (18)	−0.006 (2)	0.019 (2)
C1	0.084	0.084	0.084	0.000	0.000	0.000
O2	0.0345 (17)	0.0361 (19)	0.105 (3)	0.0031 (15)	0.0086 (19)	0.008 (2)
N3	0.041 (3)	0.083 (4)	0.076 (4)	−0.009 (3)	0.014 (3)	0.024 (3)
C2	0.072	0.072	0.072	0.000	0.000	0.000
O3	0.049 (2)	0.095 (3)	0.159 (5)	0.014 (2)	−0.002 (3)	−0.009 (3)
C3	0.091 (5)	0.102 (6)	0.106 (6)	−0.012 (4)	0.000 (5)	0.016 (5)
O4	0.052 (2)	0.129 (4)	0.131 (4)	−0.030 (3)	−0.001 (3)	−0.026 (4)
C4	0.067 (4)	0.099 (4)	0.087 (4)	−0.016 (3)	−0.010 (4)	0.024 (4)
N1	0.067 (3)	0.081 (3)	0.083 (3)	−0.019 (3)	−0.014 (3)	0.033 (3)
C5	0.040 (3)	0.037 (3)	0.074 (3)	0.005 (2)	−0.001 (3)	0.003 (2)
C6	0.082 (4)	0.073 (4)	0.080 (4)	−0.011 (3)	0.000 (3)	0.010 (3)
C7	0.041 (3)	0.034 (3)	0.072 (4)	−0.007 (2)	−0.001 (3)	0.001 (3)
C8	0.043 (3)	0.030 (3)	0.092 (4)	0.015 (2)	0.001 (3)	0.003 (3)
C9	0.048 (3)	0.053 (3)	0.037 (3)	0.011 (3)	0.002 (2)	0.010 (3)
C10	0.041 (2)	0.040 (3)	0.054 (3)	−0.006 (2)	0.009 (2)	0.015 (2)
C11	0.045 (3)	0.043 (3)	0.060 (3)	0.003 (2)	0.007 (2)	0.002 (2)
C12	0.050 (3)	0.061 (3)	0.058 (3)	0.000 (3)	−0.017 (3)	−0.004 (3)
C13	0.031 (2)	0.055 (3)	0.051 (3)	−0.005 (2)	−0.002 (2)	0.000 (2)
C14	0.040 (2)	0.038 (3)	0.067 (3)	0.000 (2)	0.008 (3)	0.002 (2)
C15	0.041	0.026	0.055	−0.003	0.013	0.003

S—C4	1.689 (7)	C4—N1	1.307 (7)
S—C6	1.716 (6)	N1—C5	1.379 (6)
N2—C9	1.330 (5)	C5—C6	1.341 (7)
N2—C7	1.442 (5)	C5—C7	1.513 (7)
N2—C8	1.496 (5)	C6—H6A	0.9300
O1—C9	1.183 (5)	C7—H7A	0.9700
C1—C3	1.477 (6)	C7—H7B	0.9700
C1—H1A	0.9600	C8—H8A	0.9600
C1—H1B	0.9600	C8—H8B	0.9600
C1—H1C	0.9600	C8—H8C	0.9600
O2—C10	1.384 (5)	C10—C15	1.355 (6)
O2—C9	1.388 (5)	C10—C11	1.387 (6)
N3—O4	1.193 (6)	C11—C12	1.415 (6)
N3—O3	1.239 (6)	C11—H11A	0.9300
N3—C13	1.502 (6)	C12—C13	1.409 (7)
C2—C3	1.411 (7)	C12—H12A	0.9300
C2—H2A	0.9600	C13—C14	1.314 (6)
C2—H2B	0.9600	C14—C15	1.398 (6)
C2—H2C	0.9600	C14—H14A	0.9300
C3—C4	1.498 (7)	C15—H15A	0.9300
C3—H3A	0.9800
C4—S—C6	90.2 (3)	S—C6—H6A	125.3
C9—N2—C7	125.8 (4)	N2—C7—C5	113.4 (4)
C9—N2—C8	115.9 (4)	N2—C7—H7A	108.9
C7—N2—C8	118.3 (4)	C5—C7—H7A	108.9
C3—C1—H1A	109.5	N2—C7—H7B	108.9
C3—C1—H1B	109.5	C5—C7—H7B	108.9
H1A—C1—H1B	109.5	H7A—C7—H7B	107.7
C3—C1—H1C	109.5	N2—C8—H8A	109.5
H1A—C1—H1C	109.5	N2—C8—H8B	109.5
H1B—C1—H1C	109.5	H8A—C8—H8B	109.5
C10—O2—C9	118.4 (4)	N2—C8—H8C	109.5
O4—N3—O3	126.3 (5)	H8A—C8—H8C	109.5
O4—N3—C13	120.6 (5)	H8B—C8—H8C	109.5
O3—N3—C13	113.1 (5)	O1—C9—N2	128.3 (5)
C3—C2—H2A	109.5	O1—C9—O2	123.0 (4)
C3—C2—H2B	109.5	N2—C9—O2	108.5 (4)
H2A—C2—H2B	109.5	C15—C10—O2	118.6 (4)
C3—C2—H2C	109.5	C15—C10—C11	120.8 (4)
H2A—C2—H2C	109.5	O2—C10—C11	120.2 (4)
H2B—C2—H2C	109.5	C10—C11—C12	119.9 (5)
C2—C3—C1	130.9 (6)	C10—C11—H11A	120.0
C2—C3—C4	116.5 (5)	C12—C11—H11A	120.0
C1—C3—C4	112.6 (6)	C13—C12—C11	115.6 (5)
C2—C3—H3A	90.1	C13—C12—H12A	122.2
C1—C3—H3A	90.1	C11—C12—H12A	122.2
C4—C3—H3A	90.1	C14—C13—C12	124.3 (4)
N1—C4—C3	123.1 (6)	C14—C13—N3	121.2 (5)
N1—C4—S	114.4 (5)	C12—C13—N3	114.4 (5)
C3—C4—S	122.3 (5)	C13—C14—C15	119.0 (5)
C4—N1—C5	110.7 (5)	C13—C14—H14A	120.5
C6—C5—N1	115.2 (5)	C15—C14—H14A	120.5
C6—C5—C7	127.1 (5)	C10—C15—C14	120.3 (5)
N1—C5—C7	117.6 (5)	C10—C15—H15A	119.9
C5—C6—S	109.5 (5)	C14—C15—H15A	119.9
C5—C6—H6A	125.3
C2—C3—C4—N1	−120.0 (7)	C8—N2—C9—O2	−178.4 (4)
C1—C3—C4—N1	59.8 (9)	C10—O2—C9—O1	−16.1 (7)
C2—C3—C4—S	55.9 (8)	C10—O2—C9—N2	168.8 (4)
C1—C3—C4—S	−124.4 (6)	C9—O2—C10—C15	135.6 (4)
C6—S—C4—N1	−1.3 (5)	C9—O2—C10—C11	−51.9 (6)
C6—S—C4—C3	−177.5 (6)	C15—C10—C11—C12	0.5 (7)
C3—C4—N1—C5	178.2 (5)	O2—C10—C11—C12	−171.8 (4)
S—C4—N1—C5	2.1 (7)	C10—C11—C12—C13	−0.8 (7)
C4—N1—C5—C6	−2.0 (7)	C11—C12—C13—C14	2.1 (8)
C4—N1—C5—C7	179.1 (5)	C11—C12—C13—N3	178.8 (4)
N1—C5—C6—S	1.0 (6)	O4—N3—C13—C14	178.0 (5)
C7—C5—C6—S	179.8 (4)	O3—N3—C13—C14	−0.6 (7)
C4—S—C6—C5	0.1 (5)	O4—N3—C13—C12	1.1 (7)
C9—N2—C7—C5	−97.3 (5)	O3—N3—C13—C12	−177.5 (5)
C8—N2—C7—C5	84.9 (5)	C12—C13—C14—C15	−2.9 (8)
C6—C5—C7—N2	10.8 (7)	N3—C13—C14—C15	−179.5 (4)
N1—C5—C7—N2	−170.4 (4)	O2—C10—C15—C14	171.1 (4)
C7—N2—C9—O1	−171.1 (5)	C11—C10—C15—C14	−1.3 (7)
C8—N2—C9—O1	6.8 (8)	C13—C14—C15—C10	2.5 (7)
C7—N2—C9—O2	3.7 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2C···O4i	0.96	2.58	3.493 (7)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2C⋯O4i	0.96	2.58	3.493 (7)	159

Symmetry code: (i) .