Phenyl N-(5-chloro-2-nitro-phenyl)carbamate.

In the title compound, C(13)H(9)ClN(2)O(4), the dihedral angle between the benzene rings is 79.5 (1)°. The mean plane of the carbamate group makes angles of 7.4 (2) and 73.6 (2)° with the mean planes of the two benzene rings. In the crystal, weak C-H⋯O inter-actions are observed between the mol-ecules, connecting them into a two-dimensional network.

Related literature

For details of dovitinib, of which the title compound is a derivative, see: Huynh (2010 ▶). For the synthesis of the title compound, see: Bandgar et al. (2011 ▶). For bond lengths, see: Zhu et al. (2007 ▶).

Experimental

Crystal data

C13H9ClN2O4

M = 292.67

Monoclinic,

a = 8.4760 (17) Å

b = 5.9270 (12) Å

c = 24.996 (5) Å

β = 94.77 (3)°

V = 1251.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 293 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 = 0.910, T max = 0.969

2466 measured reflections

2300 independent reflections

1593 reflections with I > 2σ(I)

R int = 0.084

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.155

S = 1.00

2300 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812030930/jj2143sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030930/jj2143Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812030930/jj2143Isup3.cml

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

C13H9ClN2O4	F(000) = 600
Mr = 292.67	Dx = 1.553 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 8.4760 (17) Å	θ = 9–13°
b = 5.9270 (12) Å	µ = 0.32 mm−1
c = 24.996 (5) Å	T = 293 K
β = 94.77 (3)°	Block, yellow
V = 1251.4 (4) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1593 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.084
Graphite monochromator	θmax = 25.4°, θmin = 1.6°
ω/2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = 0→7
Tmin = 0.910, Tmax = 0.969	l = −30→30
2466 measured reflections	3 standard reflections every 200 reflections
2300 independent reflections	intensity decay: 1%

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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.155	w = 1/[σ2(Fo2) + (0.095P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2300 reflections	Δρmax = 0.22 e Å−3
182 parameters	Δρmin = −0.22 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.022 (4)

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
Cl	0.57503 (11)	0.19442 (15)	−0.05438 (3)	0.0609 (3)
O1	1.0095 (3)	0.7195 (4)	0.14287 (9)	0.0616 (7)
N1	0.9731 (3)	0.7720 (4)	0.09605 (10)	0.0423 (6)
C1	0.7096 (3)	0.2956 (5)	0.04383 (11)	0.0414 (7)
H1A	0.6625	0.1637	0.0548	0.050*
O2	1.0200 (3)	0.9469 (4)	0.07710 (9)	0.0662 (7)
N2	0.8211 (3)	0.3679 (4)	0.13502 (9)	0.0459 (6)
H2A	0.8800	0.4568	0.1552	0.055*
C2	0.6891 (3)	0.3616 (5)	−0.00907 (11)	0.0440 (7)
O3	0.6855 (3)	0.0324 (4)	0.14033 (8)	0.0499 (6)
C3	0.7548 (4)	0.5578 (5)	−0.02738 (12)	0.0515 (8)
H3A	0.7379	0.6001	−0.0632	0.062*
O4	0.7949 (3)	0.2174 (4)	0.21348 (8)	0.0523 (6)
C4	0.8447 (4)	0.6877 (5)	0.00832 (11)	0.0455 (7)
H4A	0.8895	0.8203	−0.0033	0.055*
C5	0.8702 (3)	0.6245 (5)	0.06190 (11)	0.0380 (7)
C6	0.8009 (3)	0.4261 (5)	0.08095 (11)	0.0370 (6)
C7	0.7591 (3)	0.1870 (5)	0.16017 (11)	0.0384 (7)
C8	0.7459 (3)	0.0532 (5)	0.24940 (10)	0.0400 (7)
C9	0.6295 (4)	0.1140 (5)	0.28161 (12)	0.0458 (7)
H9A	0.5780	0.2521	0.2771	0.055*
C10	0.5908 (4)	−0.0359 (6)	0.32108 (12)	0.0546 (9)
H10A	0.5124	0.0013	0.3434	0.066*
C11	0.6686 (4)	−0.2403 (6)	0.32724 (12)	0.0563 (9)
H11A	0.6420	−0.3405	0.3537	0.068*
C12	0.7838 (4)	−0.2955 (6)	0.29484 (13)	0.0575 (9)
H12A	0.8357	−0.4334	0.2993	0.069*
C13	0.8247 (4)	−0.1489 (5)	0.25529 (12)	0.0487 (8)
H13A	0.9037	−0.1863	0.2332	0.058*

	U11	U22	U33	U12	U13	U23
Cl	0.0763 (6)	0.0643 (6)	0.0401 (5)	−0.0168 (4)	−0.0063 (4)	−0.0024 (4)
O1	0.0783 (17)	0.0571 (14)	0.0470 (14)	−0.0243 (12)	−0.0099 (11)	0.0075 (11)
N1	0.0454 (14)	0.0396 (14)	0.0428 (14)	−0.0047 (11)	0.0083 (11)	0.0038 (11)
C1	0.0463 (17)	0.0399 (16)	0.0381 (15)	−0.0066 (13)	0.0039 (12)	0.0038 (13)
O2	0.0900 (18)	0.0517 (14)	0.0564 (15)	−0.0300 (13)	0.0034 (12)	0.0098 (11)
N2	0.0598 (16)	0.0443 (14)	0.0329 (13)	−0.0182 (12)	−0.0011 (11)	0.0030 (11)
C2	0.0477 (18)	0.0470 (17)	0.0368 (16)	−0.0028 (14)	0.0005 (12)	0.0010 (13)
O3	0.0651 (14)	0.0470 (12)	0.0369 (11)	−0.0183 (11)	−0.0002 (9)	0.0031 (9)
C3	0.067 (2)	0.0513 (19)	0.0356 (16)	−0.0035 (16)	0.0020 (14)	0.0082 (14)
O4	0.0728 (15)	0.0521 (13)	0.0311 (11)	−0.0239 (11)	−0.0018 (10)	0.0077 (9)
C4	0.0550 (18)	0.0428 (17)	0.0391 (16)	−0.0037 (14)	0.0059 (13)	0.0097 (13)
C5	0.0383 (15)	0.0365 (15)	0.0394 (15)	−0.0021 (12)	0.0050 (12)	−0.0005 (12)
C6	0.0396 (15)	0.0377 (15)	0.0338 (14)	0.0009 (12)	0.0038 (11)	0.0032 (12)
C7	0.0391 (15)	0.0413 (16)	0.0344 (15)	−0.0010 (13)	0.0010 (12)	0.0036 (13)
C8	0.0473 (17)	0.0441 (17)	0.0276 (14)	−0.0128 (14)	−0.0021 (12)	0.0062 (12)
C9	0.0500 (18)	0.0413 (16)	0.0452 (17)	−0.0027 (14)	−0.0006 (13)	−0.0022 (13)
C10	0.058 (2)	0.067 (2)	0.0403 (17)	−0.0212 (18)	0.0119 (14)	−0.0078 (16)
C11	0.078 (2)	0.054 (2)	0.0351 (16)	−0.0228 (19)	−0.0020 (16)	0.0113 (15)
C12	0.071 (2)	0.0434 (19)	0.055 (2)	−0.0017 (17)	−0.0110 (17)	0.0074 (16)
C13	0.0496 (18)	0.0526 (19)	0.0437 (17)	−0.0007 (15)	0.0033 (13)	−0.0023 (14)

Cl—C2	1.737 (3)	O4—C8	1.410 (3)
O1—N1	1.226 (3)	C4—C5	1.390 (4)
N1—O2	1.220 (3)	C4—H4A	0.9300
N1—C5	1.459 (4)	C5—C6	1.415 (4)
C1—C2	1.376 (4)	C8—C9	1.372 (4)
C1—C6	1.392 (4)	C8—C13	1.374 (4)
C1—H1A	0.9300	C9—C10	1.387 (4)
N2—C7	1.369 (4)	C9—H9A	0.9300
N2—C6	1.391 (3)	C10—C11	1.382 (5)
N2—H2A	0.8600	C10—H10A	0.9300
C2—C3	1.384 (4)	C11—C12	1.360 (5)
O3—C7	1.193 (3)	C11—H11A	0.9300
C3—C4	1.363 (4)	C12—C13	1.382 (4)
C3—H3A	0.9300	C12—H12A	0.9300
O4—C7	1.354 (3)	C13—H13A	0.9300
O2—N1—O1	121.5 (3)	N2—C6—C5	120.8 (2)
O2—N1—C5	118.7 (2)	C1—C6—C5	117.4 (2)
O1—N1—C5	119.8 (2)	O3—C7—O4	125.3 (3)
C2—C1—C6	120.1 (3)	O3—C7—N2	128.2 (3)
C2—C1—H1A	119.9	O4—C7—N2	106.6 (2)
C6—C1—H1A	119.9	C9—C8—C13	122.2 (3)
C7—N2—C6	128.3 (2)	C9—C8—O4	117.2 (3)
C7—N2—H2A	115.9	C13—C8—O4	120.3 (3)
C6—N2—H2A	115.9	C8—C9—C10	118.2 (3)
C1—C2—C3	122.3 (3)	C8—C9—H9A	120.9
C1—C2—Cl	118.9 (2)	C10—C9—H9A	120.9
C3—C2—Cl	118.8 (2)	C11—C10—C9	120.2 (3)
C4—C3—C2	118.5 (3)	C11—C10—H10A	119.9
C4—C3—H3A	120.8	C9—C10—H10A	119.9
C2—C3—H3A	120.8	C12—C11—C10	120.3 (3)
C7—O4—C8	118.8 (2)	C12—C11—H11A	119.9
C3—C4—C5	120.8 (3)	C10—C11—H11A	119.9
C3—C4—H4A	119.6	C11—C12—C13	120.7 (3)
C5—C4—H4A	119.6	C11—C12—H12A	119.7
C4—C5—C6	120.8 (3)	C13—C12—H12A	119.7
C4—C5—N1	116.1 (2)	C8—C13—C12	118.5 (3)
C6—C5—N1	123.1 (2)	C8—C13—H13A	120.8
N2—C6—C1	121.8 (2)	C12—C13—H13A	120.8
C6—C1—C2—C3	−0.9 (5)	C4—C5—C6—C1	1.3 (4)
C6—C1—C2—Cl	179.8 (2)	N1—C5—C6—C1	−177.7 (3)
C1—C2—C3—C4	1.0 (5)	C8—O4—C7—O3	1.5 (4)
Cl—C2—C3—C4	−179.7 (2)	C8—O4—C7—N2	−179.5 (2)
C2—C3—C4—C5	0.1 (5)	C6—N2—C7—O3	6.6 (5)
C3—C4—C5—C6	−1.3 (5)	C6—N2—C7—O4	−172.3 (3)
C3—C4—C5—N1	177.8 (3)	C7—O4—C8—C9	−111.0 (3)
O2—N1—C5—C4	5.3 (4)	C7—O4—C8—C13	75.8 (3)
O1—N1—C5—C4	−175.2 (3)	C13—C8—C9—C10	−0.4 (4)
O2—N1—C5—C6	−175.6 (3)	O4—C8—C9—C10	−173.4 (2)
O1—N1—C5—C6	3.9 (4)	C8—C9—C10—C11	0.0 (4)
C7—N2—C6—C1	−0.6 (5)	C9—C10—C11—C12	0.3 (5)
C7—N2—C6—C5	178.0 (3)	C10—C11—C12—C13	−0.1 (5)
C2—C1—C6—N2	178.4 (3)	C9—C8—C13—C12	0.5 (4)
C2—C1—C6—C5	−0.2 (4)	O4—C8—C13—C12	173.3 (3)
C4—C5—C6—N2	−177.3 (3)	C11—C12—C13—C8	−0.2 (5)
N1—C5—C6—N2	3.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O2i	0.93	2.48	3.312 (4)	150
C13—H13A···O1ii	0.93	2.56	3.419 (4)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O2i	0.93	2.48	3.312 (4)	150
C13—H13A⋯O1ii	0.93	2.56	3.419 (4)	154

Symmetry codes: (i) ; (ii) .