4-Nitro-phenyl N-phenyl-carbamate.

The title compound, C(13)H(10)N(2)O(4), was synthesized as an inter-mediate for the preparation of ureas. The two aromatic rings are twisted about the central carbamate group with a C-C-N-C torsion angle of 139.6 (2)° and a C-C-O-C torsion angle of 95.9 (2)°. The mol-ecules are linked into one-dimensional chains by N-H⋯O hydrogen bonds along the b axis. Weak inter-actions between O atoms of the nitro groups (O⋯O = 3.012 Å) connect two adjacent chains.

Related literature

For related literature, see: Allen et al. (1987 ▶); Izdebski & Pawlak (1989 ▶); Olma et al. (2006 ▶); Tye et al. (2002 ▶).

Experimental

Crystal data

C13H10N2O4

M = 258.23

Monoclinic,

a = 6.0170 (2) Å

b = 5.0650 (1) Å

c = 18.8960 (5) Å

β = 92.538 (1)°

V = 575.31 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 90 (2) K

0.50 × 0.40 × 0.26 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.946, T max = 0.971

2630 measured reflections

1473 independent reflections

1363 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.104

S = 1.14

1473 reflections

172 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.32 e Å−3

Data collection: COLLECT (Nonius, 2002 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO–SMN (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1995 ▶); software used to prepare material for publication: SHELXL97 and local procedures.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807068274/fl2180sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068274/fl2180Isup2.hkl

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

C13H10N2O4	F000 = 268
Mr = 258.23	Dx = 1.491 Mg m−3
Monoclinic, P21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P2yb	Cell parameters from 1469 reflections
a = 6.0170 (2) Å	θ = 1–27.5º
b = 5.0650 (1) Å	µ = 0.11 mm−1
c = 18.8960 (5) Å	T = 90 (2) K
β = 92.538 (1)º	Block, colorless
V = 575.31 (3) Å3	0.50 × 0.40 × 0.26 mm
Z = 2

Nonius KappaCCD diffractometer	1473 independent reflections
Radiation source: fine-focus sealed tube	1363 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.020
Detector resolution: 18 pixels mm-1	θmax = 27.5º
T = 90(2) K	θmin = 1.1º
ω scans at fixed χ = 55°	h = −7→7
Absorption correction: multi-scan(SCALEPACK; Otwinowski & Minor, 1997)	k = −6→6
Tmin = 0.946, Tmax = 0.971	l = −24→24
2630 measured reflections

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)] = 0.038	H-atom parameters constrained
wR(F2) = 0.104	w = 1/[σ2(Fo2) + (0.0582P)2 + 0.1763P] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max = 0.009
1473 reflections	Δρmax = 0.24 e Å−3
172 parameters	Δρmin = −0.32 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
C1	0.9665 (3)	0.7781 (5)	0.84935 (11)	0.0179 (5)
N1	0.7888 (3)	0.8052 (4)	0.79739 (10)	0.0185 (4)
H1	0.7443	0.9655	0.7857	0.022*
N2	0.0763 (3)	−0.1088 (4)	0.56535 (9)	0.0180 (4)
O1	0.7161 (3)	0.3675 (4)	0.77761 (9)	0.0227 (4)
O2	0.5362 (3)	0.6890 (3)	0.71426 (8)	0.0196 (4)
O3	−0.1087 (2)	−0.1712 (4)	0.58598 (9)	0.0248 (4)
O4	0.1657 (3)	−0.2175 (4)	0.51627 (8)	0.0231 (4)
C2	1.1431 (4)	0.9546 (5)	0.84631 (12)	0.0219 (5)
H2	1.1414	1.0883	0.8110	0.026*
C3	1.3226 (4)	0.9341 (6)	0.89534 (12)	0.0248 (5)
H3	1.4432	1.0546	0.8935	0.030*
C4	1.3255 (4)	0.7399 (6)	0.94631 (12)	0.0257 (6)
H4	1.4489	0.7249	0.9792	0.031*
C5	1.1480 (4)	0.5660 (6)	0.94961 (12)	0.0261 (5)
H5	1.1498	0.4330	0.9851	0.031*
C6	0.9670 (4)	0.5853 (6)	0.90111 (11)	0.0214 (5)
H6	0.8451	0.4669	0.9037	0.026*
C7	0.6852 (4)	0.5994 (5)	0.76518 (11)	0.0169 (4)
C8	0.4214 (4)	0.4908 (5)	0.67556 (11)	0.0177 (5)
C9	0.5166 (3)	0.3802 (5)	0.61711 (11)	0.0190 (5)
H9	0.6578	0.4381	0.6027	0.023*
C10	0.4012 (4)	0.1825 (5)	0.58006 (11)	0.0187 (5)
H10	0.4625	0.1017	0.5400	0.022*
C11	0.1954 (3)	0.1055 (5)	0.60271 (11)	0.0161 (4)
C12	0.0975 (4)	0.2213 (5)	0.65993 (11)	0.0189 (5)
H12	−0.0457	0.1672	0.6735	0.023*
C13	0.2135 (4)	0.4187 (5)	0.69708 (11)	0.0198 (5)
H13	0.1508	0.5024	0.7365	0.024*

	U11	U22	U33	U12	U13	U23
C1	0.0170 (10)	0.0182 (11)	0.0183 (9)	0.0038 (10)	−0.0015 (7)	−0.0028 (9)
N1	0.0191 (9)	0.0118 (9)	0.0241 (9)	0.0013 (8)	−0.0045 (7)	−0.0005 (8)
N2	0.0152 (9)	0.0161 (10)	0.0224 (8)	−0.0008 (8)	−0.0022 (7)	0.0029 (9)
O1	0.0238 (8)	0.0150 (9)	0.0286 (8)	0.0000 (7)	−0.0060 (6)	0.0001 (7)
O2	0.0188 (8)	0.0154 (8)	0.0240 (7)	−0.0009 (7)	−0.0058 (6)	−0.0014 (7)
O3	0.0153 (7)	0.0257 (10)	0.0334 (8)	−0.0076 (8)	0.0006 (6)	0.0016 (8)
O4	0.0207 (8)	0.0215 (9)	0.0269 (8)	0.0002 (8)	−0.0016 (6)	−0.0052 (8)
C2	0.0230 (11)	0.0208 (13)	0.0218 (10)	−0.0031 (10)	−0.0008 (8)	0.0009 (10)
C3	0.0205 (11)	0.0267 (14)	0.0269 (11)	−0.0036 (10)	−0.0020 (8)	−0.0045 (10)
C4	0.0218 (11)	0.0264 (14)	0.0280 (11)	0.0036 (11)	−0.0076 (9)	−0.0041 (11)
C5	0.0303 (13)	0.0235 (13)	0.0238 (10)	0.0022 (12)	−0.0061 (9)	0.0027 (11)
C6	0.0215 (11)	0.0204 (12)	0.0221 (10)	−0.0020 (11)	−0.0017 (8)	0.0002 (10)
C7	0.0163 (10)	0.0155 (11)	0.0190 (9)	0.0017 (9)	0.0008 (7)	−0.0003 (9)
C8	0.0188 (10)	0.0130 (11)	0.0209 (10)	−0.0012 (10)	−0.0049 (8)	0.0010 (9)
C9	0.0127 (9)	0.0196 (12)	0.0244 (10)	−0.0032 (10)	−0.0012 (8)	0.0019 (10)
C10	0.0151 (10)	0.0198 (11)	0.0212 (9)	−0.0010 (9)	0.0013 (8)	−0.0002 (9)
C11	0.0133 (10)	0.0146 (10)	0.0200 (9)	−0.0004 (9)	−0.0039 (7)	0.0013 (9)
C12	0.0151 (10)	0.0201 (13)	0.0215 (10)	0.0008 (9)	0.0004 (8)	0.0019 (9)
C13	0.0191 (10)	0.0201 (12)	0.0203 (9)	0.0011 (10)	0.0012 (8)	−0.0004 (9)

C1—C6	1.382 (3)	C4—C5	1.388 (4)
C1—C2	1.392 (4)	C4—H4	0.9500
C1—N1	1.426 (3)	C5—C6	1.396 (3)
N1—C7	1.346 (3)	C5—H5	0.9500
N1—H1	0.8800	C6—H6	0.9500
N2—O4	1.224 (3)	C8—C13	1.381 (3)
N2—O3	1.237 (2)	C8—C9	1.385 (3)
N2—C11	1.465 (3)	C9—C10	1.390 (3)
O1—C7	1.210 (3)	C9—H9	0.9500
O2—C7	1.364 (3)	C10—C11	1.384 (3)
O2—C8	1.405 (3)	C10—H10	0.9500
C2—C3	1.395 (3)	C11—C12	1.385 (3)
C2—H2	0.9500	C12—C13	1.391 (3)
C3—C4	1.376 (4)	C12—H12	0.9500
C3—H3	0.9500	C13—H13	0.9500
C6—C1—C2	120.4 (2)	C1—C6—H6	120.3
C6—C1—N1	122.2 (2)	C5—C6—H6	120.3
C2—C1—N1	117.4 (2)	O1—C7—N1	126.8 (2)
C7—N1—C1	123.7 (2)	O1—C7—O2	123.4 (2)
C7—N1—H1	118.1	N1—C7—O2	109.8 (2)
C1—N1—H1	118.1	C13—C8—C9	122.7 (2)
O4—N2—O3	123.8 (2)	C13—C8—O2	117.8 (2)
O4—N2—C11	118.45 (18)	C9—C8—O2	119.5 (2)
O3—N2—C11	117.76 (19)	C8—C9—C10	118.6 (2)
C7—O2—C8	114.97 (19)	C8—C9—H9	120.7
C3—C2—C1	119.7 (2)	C10—C9—H9	120.7
C3—C2—H2	120.2	C11—C10—C9	118.8 (2)
C1—C2—H2	120.2	C11—C10—H10	120.6
C4—C3—C2	120.2 (2)	C9—C10—H10	120.6
C4—C3—H3	119.9	C10—C11—C12	122.7 (2)
C2—C3—H3	119.9	C10—C11—N2	119.0 (2)
C3—C4—C5	120.0 (2)	C12—C11—N2	118.30 (19)
C3—C4—H4	120.0	C11—C12—C13	118.5 (2)
C5—C4—H4	120.0	C11—C12—H12	120.8
C4—C5—C6	120.4 (2)	C13—C12—H12	120.8
C4—C5—H5	119.8	C8—C13—C12	118.8 (2)
C6—C5—H5	119.8	C8—C13—H13	120.6
C1—C6—C5	119.4 (2)	C12—C13—H13	120.6
C6—C1—N1—C7	−40.3 (3)	C7—O2—C8—C9	−85.5 (3)
C2—C1—N1—C7	139.6 (2)	C13—C8—C9—C10	−2.2 (4)
C6—C1—C2—C3	0.8 (4)	O2—C8—C9—C10	179.3 (2)
N1—C1—C2—C3	−179.1 (2)	C8—C9—C10—C11	0.5 (3)
C1—C2—C3—C4	0.2 (4)	C9—C10—C11—C12	1.4 (4)
C2—C3—C4—C5	−0.9 (4)	C9—C10—C11—N2	−178.0 (2)
C3—C4—C5—C6	0.5 (4)	O4—N2—C11—C10	1.8 (3)
C2—C1—C6—C5	−1.1 (4)	O3—N2—C11—C10	−179.0 (2)
N1—C1—C6—C5	178.8 (2)	O4—N2—C11—C12	−177.6 (2)
C4—C5—C6—C1	0.5 (4)	O3—N2—C11—C12	1.6 (3)
C1—N1—C7—O1	4.5 (4)	C10—C11—C12—C13	−1.6 (4)
C1—N1—C7—O2	−174.95 (18)	N2—C11—C12—C13	177.8 (2)
C8—O2—C7—O1	−1.1 (3)	C9—C8—C13—C12	2.0 (4)
C8—O2—C7—N1	178.43 (18)	O2—C8—C13—C12	−179.5 (2)
C7—O2—C8—C13	95.9 (2)	C11—C12—C13—C8	−0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.88	2.05	2.903 (3)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.88	2.05	2.903 (3)	164

Symmetry code: (i) .