3-Fluoro-4-nitro-phenyl 4-methyl-benzene-sulfonate.

In the title compound, C(13)H(10)FNO(5)S, the dihedral angle between the benzene rings is 47.63 (14)°. In the crystal, π-π stacking occurs between nearly parallel benzene rings of adjacent mol-ecules, the centroid-centroid distance being 3.7806 (16) Å. Weak inter-molecular C-H⋯O hydrogen bonding is also present in the crystal structure.

Related literature

For related compounds and their biological activity, see: Cho et al. (2003) ▶; Marson et al. (2007 ▶).

Experimental

Crystal data

C13H10FNO5S

M = 311.28

Orthorhombic,

a = 14.2596 (5) Å

b = 11.4800 (3) Å

c = 8.3602 (2) Å

V = 1368.57 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 293 K

0.30 × 0.30 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006 ▶) T min = 0.979, T max = 1.0

10802 measured reflections

2251 independent reflections

1855 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.083

S = 1.05

2251 reflections

191 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 752 Friedel pairs

Flack parameter: −0.06 (9)

Data collection: CrysAlis PRO (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811005903/xu5126sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811005903/xu5126Isup2.hkl

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

C13H10FNO5S	F(000) = 640
Mr = 311.28	Dx = 1.511 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2c -2n	Cell parameters from 4234 reflections
a = 14.2596 (5) Å	θ = 2.9–29.1°
b = 11.4800 (3) Å	µ = 0.27 mm−1
c = 8.3602 (2) Å	T = 293 K
V = 1368.57 (7) Å3	Block, colorless
Z = 4	0.30 × 0.30 × 0.20 mm

Oxford Diffraction Xcalibur Eos diffractometer	2251 independent reflections
Radiation source: fine-focus sealed tube	1855 reflections with I > 2σ(I)
graphite	Rint = 0.025
Detector resolution: 16.0874 pixels mm-1	θmax = 26.4°, θmin = 2.9°
ω scans	h = −17→17
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	k = −14→14
Tmin = 0.979, Tmax = 1.0	l = −7→10
10802 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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.083	w = 1/[σ2(Fo2) + (0.039P)2 + 0.1799P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.025
2251 reflections	Δρmax = 0.12 e Å−3
191 parameters	Δρmin = −0.22 e Å−3
1 restraint	Absolute structure: Flack (1983), 752 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.06 (9)

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	0.16636 (4)	0.27076 (5)	0.58998 (10)	0.05567 (19)
F1	0.34171 (15)	−0.14722 (14)	0.6292 (3)	0.1007 (7)
O1	0.56870 (17)	−0.0441 (2)	0.8899 (4)	0.0906 (8)
O2	0.51366 (19)	−0.1649 (2)	0.7187 (3)	0.1041 (9)
O3	0.18775 (13)	0.20401 (17)	0.7566 (2)	0.0574 (5)
O4	0.16341 (14)	0.18606 (19)	0.4665 (3)	0.0675 (6)
O5	0.08578 (12)	0.33777 (18)	0.6260 (3)	0.0788 (7)
N1	0.5080 (2)	−0.0778 (2)	0.7989 (3)	0.0675 (7)
C1	0.4217 (2)	−0.0077 (2)	0.7863 (4)	0.0523 (7)
C2	0.3442 (2)	−0.0442 (2)	0.7026 (4)	0.0601 (8)
C3	0.2660 (2)	0.0248 (2)	0.6906 (4)	0.0580 (7)
H3	0.2136	−0.0003	0.6341	0.070*
C4	0.26682 (18)	0.1317 (2)	0.7636 (3)	0.0474 (6)
C5	0.3427 (2)	0.1698 (2)	0.8491 (4)	0.0548 (7)
H5	0.3417	0.2424	0.8987	0.066*
C6	0.4204 (2)	0.0995 (2)	0.8609 (4)	0.0566 (7)
H6	0.4722	0.1243	0.9192	0.068*
C7	0.26414 (17)	0.3597 (2)	0.5642 (3)	0.0468 (6)
C8	0.33831 (18)	0.3209 (2)	0.4704 (4)	0.0532 (7)
H8	0.3359	0.2483	0.4213	0.064*
C9	0.41530 (18)	0.3917 (2)	0.4512 (4)	0.0538 (7)
H9	0.4659	0.3650	0.3914	0.065*
C10	0.41940 (19)	0.5008 (2)	0.5179 (3)	0.0519 (7)
C11	0.34570 (19)	0.5373 (2)	0.6128 (4)	0.0584 (7)
H11	0.3483	0.6103	0.6609	0.070*
C12	0.26858 (19)	0.4679 (2)	0.6375 (3)	0.0551 (7)
H12	0.2198	0.4931	0.7028	0.066*
C13	0.5028 (2)	0.5786 (3)	0.4867 (5)	0.0752 (9)
H13A	0.4860	0.6370	0.4096	0.113*
H13B	0.5537	0.5327	0.4460	0.113*
H13C	0.5215	0.6155	0.5847	0.113*

	U11	U22	U33	U12	U13	U23
S1	0.0420 (3)	0.0668 (4)	0.0582 (4)	0.0045 (3)	−0.0005 (4)	0.0083 (4)
F1	0.1299 (17)	0.0508 (9)	0.1214 (18)	0.0063 (10)	−0.0321 (16)	−0.0197 (11)
O1	0.0640 (15)	0.0999 (18)	0.108 (2)	0.0104 (14)	−0.0161 (15)	0.0259 (17)
O2	0.135 (2)	0.0934 (17)	0.0836 (18)	0.0580 (16)	−0.0025 (17)	−0.0028 (15)
O3	0.0489 (11)	0.0689 (12)	0.0543 (12)	0.0047 (9)	0.0104 (10)	0.0087 (10)
O4	0.0635 (14)	0.0765 (13)	0.0625 (13)	−0.0099 (10)	−0.0104 (11)	−0.0038 (11)
O5	0.0452 (11)	0.0901 (14)	0.1011 (19)	0.0158 (9)	0.0081 (13)	0.0152 (14)
N1	0.0737 (19)	0.0709 (17)	0.0579 (17)	0.0151 (14)	0.0075 (15)	0.0231 (15)
C1	0.0533 (18)	0.0547 (16)	0.0487 (17)	0.0054 (12)	0.0020 (14)	0.0132 (14)
C2	0.078 (2)	0.0415 (14)	0.0605 (19)	−0.0031 (14)	−0.0059 (17)	0.0043 (14)
C3	0.0585 (17)	0.0529 (15)	0.0627 (19)	−0.0129 (13)	−0.0115 (15)	0.0035 (14)
C4	0.0457 (14)	0.0534 (14)	0.0430 (15)	−0.0017 (11)	0.0040 (13)	0.0085 (12)
C5	0.0580 (17)	0.0520 (15)	0.0543 (17)	−0.0027 (13)	−0.0022 (15)	0.0005 (13)
C6	0.0557 (18)	0.0606 (17)	0.0534 (18)	−0.0076 (14)	−0.0060 (15)	0.0069 (14)
C7	0.0431 (13)	0.0520 (13)	0.0453 (17)	0.0104 (10)	0.0012 (13)	0.0046 (13)
C8	0.0524 (16)	0.0467 (13)	0.0604 (17)	0.0088 (12)	0.0042 (15)	−0.0067 (13)
C9	0.0453 (15)	0.0563 (16)	0.0597 (18)	0.0090 (12)	0.0078 (14)	−0.0005 (14)
C10	0.0506 (16)	0.0555 (16)	0.0497 (17)	0.0051 (12)	−0.0056 (13)	0.0021 (12)
C11	0.0692 (18)	0.0491 (13)	0.0568 (18)	0.0042 (12)	−0.0026 (18)	−0.0081 (14)
C12	0.0601 (17)	0.0582 (15)	0.0471 (17)	0.0176 (12)	0.0093 (14)	−0.0015 (13)
C13	0.069 (2)	0.0714 (19)	0.085 (2)	−0.0119 (15)	0.001 (2)	−0.0069 (18)

S1—O3	1.619 (2)	C5—C6	1.374 (4)
S1—O4	1.419 (2)	C6—H6	0.9300
S1—O5	1.4152 (19)	C7—C8	1.390 (4)
S1—C7	1.741 (3)	C7—C12	1.386 (3)
F1—C2	1.332 (3)	C8—H8	0.9300
O1—N1	1.216 (4)	C8—C9	1.375 (3)
O2—N1	1.206 (3)	C9—H9	0.9300
O3—C4	1.401 (3)	C9—C10	1.373 (4)
N1—C1	1.475 (4)	C10—C11	1.382 (4)
C1—C2	1.374 (4)	C10—C13	1.509 (4)
C1—C6	1.380 (4)	C11—H11	0.9300
C2—C3	1.372 (4)	C11—C12	1.374 (4)
C3—H3	0.9300	C12—H12	0.9300
C3—C4	1.371 (4)	C13—H13A	0.9600
C4—C5	1.369 (4)	C13—H13B	0.9600
C5—H5	0.9300	C13—H13C	0.9600
F1—C2—C1	121.8 (3)	C6—C1—N1	117.8 (3)
F1—C2—C3	117.2 (3)	C6—C5—H5	120.4
O1—N1—C1	117.7 (3)	C7—C8—H8	120.5
O2—N1—O1	124.3 (3)	C7—C12—H12	120.3
O2—N1—C1	118.0 (3)	C8—C7—S1	119.45 (19)
O3—S1—C7	103.48 (11)	C8—C9—H9	119.1
O4—S1—O3	107.89 (11)	C9—C8—C7	119.0 (2)
O4—S1—C7	109.59 (13)	C9—C8—H8	120.5
O5—S1—O3	103.14 (14)	C9—C10—C11	118.5 (2)
O5—S1—O4	120.23 (14)	C9—C10—C13	120.2 (3)
O5—S1—C7	110.97 (11)	C10—C9—C8	121.7 (2)
C1—C6—H6	119.9	C10—C9—H9	119.1
C2—C1—N1	122.7 (3)	C10—C11—H11	119.4
C2—C1—C6	119.5 (3)	C10—C13—H13A	109.5
C2—C3—H3	120.7	C10—C13—H13B	109.5
C3—C2—C1	121.0 (3)	C10—C13—H13C	109.5
C3—C4—O3	120.3 (2)	C11—C10—C13	121.3 (3)
C4—O3—S1	117.93 (16)	C11—C12—C7	119.3 (2)
C4—C3—C2	118.6 (3)	C11—C12—H12	120.3
C4—C3—H3	120.7	C12—C7—S1	120.46 (19)
C4—C5—H5	120.4	C12—C7—C8	120.1 (2)
C4—C5—C6	119.1 (3)	C12—C11—C10	121.3 (2)
C5—C4—O3	118.0 (2)	C12—C11—H11	119.4
C5—C4—C3	121.7 (2)	H13A—C13—H13B	109.5
C5—C6—C1	120.2 (3)	H13A—C13—H13C	109.5
C5—C6—H6	119.9	H13B—C13—H13C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2i	0.93	2.55	3.224 (4)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2i	0.93	2.55	3.224 (4)	129

Symmetry code: (i) .