2-Chloro-1-(3-fluoro-benz-yloxy)-4-nitro-benzene.

In the title compound, C(13)H(9)ClFNO(3), the benzene rings are oriented at a dihedral angle of 41.23 (5)°. In the crystal structure, inter-molecular C-H⋯O inter-actions link the mol-ecules in a herring-bone arrangement along the b axis and weak π-π contacts between the benzene rings [centroid-centroid distance = 3.881 (1) Å] may further stabilize the structure.

Related literature

The title compound is a dual ErbB-1/ErbB-2 tyrosine kinase inhibitor, see: Petrov et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H9ClFNO3

M = 281.66

Monoclinic,

a = 8.3290 (17) Å

b = 12.640 (3) Å

c = 11.875 (2) Å

β = 96.94 (3)°

V = 1241.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 294 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 = 0.909, T max = 0.968

2411 measured reflections

2248 independent reflections

1340 reflections with I > 2σ(I)

R int = 0.028

3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.149

S = 1.01

2248 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.25 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, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680903431X/hk2758sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903431X/hk2758Isup2.hkl

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

C13H9ClFNO3	F(000) = 576
Mr = 281.66	Dx = 1.508 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 8.3290 (17) Å	θ = 9–12°
b = 12.640 (3) Å	µ = 0.32 mm−1
c = 11.875 (2) Å	T = 294 K
β = 96.94 (3)°	Block, yellow
V = 1241.0 (4) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1340 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
graphite	θmax = 25.3°, θmin = 2.4°
ω/2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = 0→15
Tmin = 0.909, Tmax = 0.968	l = −14→14
2411 measured reflections	3 standard reflections every 120 min
2248 independent reflections	intensity decay: 1%

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.07P)2] where P = (Fo2 + 2Fc2)/3
2248 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.81771 (13)	0.51262 (7)	0.07511 (8)	0.0802 (4)
F	0.4335 (3)	1.00189 (17)	−0.29984 (19)	0.0996 (8)
O1	0.6878 (3)	0.72025 (15)	0.07000 (17)	0.0582 (6)
O2	1.1588 (3)	0.5447 (2)	0.4720 (2)	0.0846 (8)
O3	1.0836 (4)	0.6867 (3)	0.5501 (2)	0.1058 (10)
N	1.0804 (3)	0.6268 (3)	0.4700 (3)	0.0694 (8)
C1	0.3405 (4)	0.8293 (3)	−0.2781 (3)	0.0670 (10)
H1A	0.2801	0.8325	−0.3492	0.080*
C2	0.4320 (4)	0.9129 (3)	−0.2358 (3)	0.0629 (9)
C3	0.5233 (4)	0.9117 (2)	−0.1320 (3)	0.0550 (8)
H3A	0.5858	0.9700	−0.1069	0.066*
C4	0.5210 (4)	0.8224 (2)	−0.0653 (3)	0.0513 (8)
C5	0.4296 (4)	0.7364 (3)	−0.1061 (3)	0.0630 (9)
H5A	0.4279	0.6756	−0.0621	0.076*
C6	0.3407 (4)	0.7401 (3)	−0.2118 (3)	0.0707 (10)
H6A	0.2801	0.6815	−0.2386	0.085*
C7	0.6137 (4)	0.8219 (2)	0.0507 (3)	0.0587 (9)
H7A	0.6959	0.8767	0.0564	0.070*
H7B	0.5415	0.8358	0.1073	0.070*
C8	0.7811 (4)	0.7033 (2)	0.1694 (3)	0.0492 (8)
C9	0.8086 (4)	0.7766 (2)	0.2567 (3)	0.0564 (8)
H9A	0.7609	0.8431	0.2488	0.068*
C10	0.9064 (4)	0.7510 (3)	0.3551 (3)	0.0597 (9)
H10A	0.9250	0.8002	0.4135	0.072*
C11	0.9755 (4)	0.6531 (2)	0.3662 (3)	0.0531 (8)
C12	0.9495 (4)	0.5787 (3)	0.2808 (3)	0.0575 (8)
H12A	0.9970	0.5122	0.2896	0.069*
C13	0.8532 (4)	0.6039 (2)	0.1836 (3)	0.0530 (8)

	U11	U22	U33	U12	U13	U23
Cl	0.1074 (8)	0.0574 (6)	0.0736 (7)	0.0078 (5)	0.0026 (5)	−0.0116 (4)
F	0.135 (2)	0.0791 (15)	0.0789 (15)	0.0098 (14)	−0.0083 (14)	0.0259 (11)
O1	0.0683 (14)	0.0475 (12)	0.0568 (14)	0.0075 (11)	−0.0005 (11)	0.0012 (10)
O2	0.0635 (17)	0.094 (2)	0.0931 (19)	0.0152 (16)	−0.0032 (14)	0.0228 (16)
O3	0.109 (2)	0.124 (3)	0.0751 (19)	0.014 (2)	−0.0258 (17)	−0.0135 (19)
N	0.0542 (18)	0.083 (2)	0.069 (2)	−0.0014 (18)	0.0016 (16)	0.0110 (18)
C1	0.061 (2)	0.083 (3)	0.055 (2)	0.011 (2)	−0.0022 (17)	−0.0035 (19)
C2	0.067 (2)	0.060 (2)	0.062 (2)	0.0124 (19)	0.0055 (18)	0.0090 (18)
C3	0.0521 (19)	0.0494 (18)	0.063 (2)	0.0055 (15)	0.0063 (16)	−0.0019 (15)
C4	0.0482 (18)	0.0511 (18)	0.0552 (19)	0.0061 (15)	0.0087 (15)	0.0009 (15)
C5	0.067 (2)	0.057 (2)	0.065 (2)	−0.0028 (18)	0.0075 (18)	0.0064 (17)
C6	0.061 (2)	0.075 (2)	0.074 (3)	−0.0052 (19)	0.001 (2)	−0.008 (2)
C7	0.068 (2)	0.0494 (19)	0.057 (2)	0.0020 (16)	0.0005 (17)	0.0031 (15)
C8	0.0461 (18)	0.0499 (18)	0.0515 (18)	−0.0016 (15)	0.0054 (15)	0.0030 (15)
C9	0.062 (2)	0.0480 (17)	0.060 (2)	0.0025 (16)	0.0068 (17)	0.0020 (16)
C10	0.060 (2)	0.063 (2)	0.056 (2)	−0.0072 (17)	0.0062 (17)	−0.0032 (16)
C11	0.0446 (18)	0.0566 (19)	0.058 (2)	−0.0012 (16)	0.0055 (15)	0.0078 (16)
C12	0.049 (2)	0.057 (2)	0.068 (2)	0.0068 (16)	0.0107 (17)	0.0077 (17)
C13	0.0534 (19)	0.0518 (19)	0.0548 (19)	−0.0026 (16)	0.0096 (16)	0.0017 (15)

Cl—C13	1.728 (3)	C5—C6	1.379 (5)
F—C2	1.359 (4)	C5—H5A	0.9300
O1—C7	1.432 (3)	C6—H6A	0.9300
O1—C8	1.350 (4)	C7—H7A	0.9700
N—O2	1.225 (4)	C7—H7B	0.9700
N—O3	1.214 (4)	C8—C9	1.388 (4)
N—C11	1.460 (4)	C8—C13	1.394 (4)
C1—C2	1.363 (5)	C9—C10	1.380 (5)
C1—C6	1.375 (4)	C9—H9A	0.9300
C1—H1A	0.9300	C10—C11	1.366 (4)
C2—C3	1.367 (4)	C10—H10A	0.9300
C3—C4	1.381 (4)	C11—C12	1.380 (4)
C3—H3A	0.9300	C12—C13	1.361 (4)
C4—C5	1.382 (4)	C12—H12A	0.9300
C4—C7	1.496 (4)
C8—O1—C7	118.3 (2)	O1—C7—H7A	110.0
O2—N—C11	118.2 (3)	C4—C7—H7A	110.0
O3—N—O2	123.5 (3)	O1—C7—H7B	110.0
O3—N—C11	118.3 (3)	C4—C7—H7B	110.0
C2—C1—C6	117.6 (3)	H7A—C7—H7B	108.4
C2—C1—H1A	121.2	O1—C8—C9	124.9 (3)
C6—C1—H1A	121.2	O1—C8—C13	116.3 (3)
F—C2—C1	118.5 (3)	C9—C8—C13	118.8 (3)
F—C2—C3	118.1 (3)	C10—C9—C8	120.3 (3)
C1—C2—C3	123.3 (3)	C10—C9—H9A	119.9
C2—C3—C4	118.7 (3)	C8—C9—H9A	119.9
C2—C3—H3A	120.6	C11—C10—C9	119.5 (3)
C4—C3—H3A	120.6	C11—C10—H10A	120.3
C3—C4—C5	119.2 (3)	C9—C10—H10A	120.3
C3—C4—C7	119.4 (3)	C10—C11—C12	121.3 (3)
C5—C4—C7	121.4 (3)	C10—C11—N	119.3 (3)
C6—C5—C4	120.3 (3)	C12—C11—N	119.4 (3)
C6—C5—H5A	119.8	C13—C12—C11	119.2 (3)
C4—C5—H5A	119.8	C13—C12—H12A	120.4
C1—C6—C5	120.8 (3)	C11—C12—H12A	120.4
C1—C6—H6A	119.6	C12—C13—C8	120.9 (3)
C5—C6—H6A	119.6	C12—C13—Cl	120.4 (3)
O1—C7—C4	108.4 (2)	C8—C13—Cl	118.6 (2)
C6—C1—C2—F	−180.0 (3)	C13—C8—C9—C10	0.3 (5)
C6—C1—C2—C3	0.3 (5)	C8—C9—C10—C11	−0.2 (5)
F—C2—C3—C4	179.1 (3)	C9—C10—C11—C12	−0.1 (5)
C1—C2—C3—C4	−1.2 (5)	C9—C10—C11—N	179.3 (3)
C2—C3—C4—C5	1.3 (5)	O3—N—C11—C10	11.0 (5)
C2—C3—C4—C7	−177.0 (3)	O2—N—C11—C10	−170.0 (3)
C3—C4—C5—C6	−0.5 (5)	O3—N—C11—C12	−169.6 (3)
C7—C4—C5—C6	177.7 (3)	O2—N—C11—C12	9.5 (4)
C2—C1—C6—C5	0.5 (5)	C10—C11—C12—C13	0.2 (5)
C4—C5—C6—C1	−0.4 (5)	N—C11—C12—C13	−179.2 (3)
C8—O1—C7—C4	178.5 (2)	C11—C12—C13—C8	−0.1 (4)
C3—C4—C7—O1	−140.2 (3)	C11—C12—C13—Cl	−179.9 (2)
C5—C4—C7—O1	41.6 (4)	O1—C8—C13—C12	−179.9 (3)
C7—O1—C8—C9	1.5 (4)	C9—C8—C13—C12	−0.2 (4)
C7—O1—C8—C13	−178.8 (3)	O1—C8—C13—Cl	−0.1 (4)
O1—C8—C9—C10	−180.0 (3)	C9—C8—C13—Cl	179.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O2i	0.97	2.49	3.423 (4)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O2i	0.97	2.49	3.423 (4)	162

Symmetry code: (i) .