4-Nitro-phenyl 4-bromo-benzene-sulfonate.

In the title mol-ecule, C(12)H(8)BrNO(5)S, the dihedral angle between the two benzene rings is 30.02 (7)°. The crystal structure is stabilized by weak C-H⋯O inter-actions.

Related literature

For a detailed account of the mol­ecular and supra­molecular architectures of aromatic sulfonates, see: Vembu et al. (2007 ▶) and references cited therein. For the uses of aromatic sulfonates, see: Alford et al. (1991 ▶); Jiang et al. (1990 ▶); Narayanan & Krakow (1983 ▶); Spungin et al. (1992 ▶); Tharakan et al. (1992 ▶); Yachi et al. (1989 ▶). For C—H⋯O inter­actions, see: Desiraju & Steiner (1999 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C12H8BrNO5S

M = 358.16

Monoclinic,

a = 13.150 (2) Å

b = 8.3387 (10) Å

c = 12.292 (2) Å

β = 105.932 (7)°

V = 1296.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 3.35 mm−1

T = 90 K

0.20 × 0.15 × 0.07 mm

Data collection

Nonius KappaCCD diffractometer with an Oxford Cryosystems Cryostream cooler

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.554, T max = 0.799

35540 measured reflections

4458 independent reflections

3518 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.085

S = 1.04

4458 reflections

213 parameters

All H-atom parameters refined

Δρmax = 0.57 e Å−3

Δρmin = −0.81 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809040033/lh2921sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040033/lh2921Isup2.hkl

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

C12H8BrNO5S	F(000) = 712
Mr = 358.16	Dx = 1.836 Mg m−3
Monoclinic, P21/c	Melting point: 376 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.150 (2) Å	Cell parameters from 4455 reflections
b = 8.3387 (10) Å	θ = 2.5–32.6°
c = 12.292 (2) Å	µ = 3.35 mm−1
β = 105.932 (7)°	T = 90 K
V = 1296.1 (3) Å3	Plate, colorless
Z = 4	0.20 × 0.15 × 0.07 mm

Nonius KappaCCD diffractometer with an Oxford Cryosystems Cryostream cooler	4458 independent reflections
Radiation source: fine-focus sealed tube	3518 reflections with I > 2σ(I)
graphite	Rint = 0.024
ω scans with κ offsets	θmax = 32.6°, θmin = 2.9°
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	h = −19→19
Tmin = 0.554, Tmax = 0.799	k = −12→12
35540 measured reflections	l = −17→18

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	All H-atom parameters refined
S = 1.03	w = 1/[σ2(Fo2) + (0.0315P)2 + 2.0753P] where P = (Fo2 + 2Fc2)/3
4458 reflections	(Δ/σ)max = 0.001
213 parameters	Δρmax = 0.57 e Å−3
0 restraints	Δρmin = −0.81 e Å−3

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
Br	0.421887 (17)	0.40490 (3)	0.26901 (2)	0.02131 (7)
S	0.78218 (4)	0.39271 (6)	0.01144 (4)	0.01524 (10)
C1	0.52731 (16)	0.3985 (3)	0.19030 (18)	0.0161 (4)
C2	0.51138 (17)	0.3089 (3)	0.09190 (19)	0.0190 (4)
C3	0.59099 (17)	0.3057 (3)	0.03702 (18)	0.0182 (4)
C4	0.68192 (16)	0.3964 (3)	0.08048 (17)	0.0150 (4)
C5	0.69638 (16)	0.4885 (3)	0.17766 (18)	0.0162 (4)
C6	0.61882 (17)	0.4870 (3)	0.23466 (18)	0.0172 (4)
O7	0.83334 (13)	0.5453 (2)	0.02325 (14)	0.0205 (3)
O8	0.74442 (13)	0.3181 (2)	−0.09633 (13)	0.0219 (3)
O9	0.86612 (12)	0.26386 (18)	0.08300 (13)	0.0166 (3)
C10	0.94553 (16)	0.3146 (2)	0.17970 (17)	0.0150 (4)
C11	0.92572 (16)	0.3055 (3)	0.28444 (18)	0.0169 (4)
C12	1.00721 (17)	0.3432 (3)	0.37986 (18)	0.0170 (4)
C13	1.10505 (16)	0.3843 (2)	0.36629 (18)	0.0156 (4)
C14	1.12437 (16)	0.3955 (3)	0.26150 (19)	0.0180 (4)
C15	1.04210 (17)	0.3612 (3)	0.16568 (19)	0.0178 (4)
N16	1.19300 (15)	0.4124 (2)	0.46863 (16)	0.0184 (3)
O17	1.17261 (14)	0.4151 (2)	0.56006 (13)	0.0234 (3)
O18	1.28217 (13)	0.4302 (2)	0.45684 (15)	0.0256 (4)
H2	0.449 (2)	0.245 (4)	0.062 (2)	0.024 (7)*
H3	0.582 (2)	0.249 (3)	−0.029 (2)	0.020 (7)*
H5	0.758 (2)	0.552 (3)	0.205 (2)	0.019 (7)*
H6	0.627 (2)	0.542 (3)	0.302 (2)	0.018 (7)*
H11	0.858 (2)	0.274 (4)	0.291 (2)	0.028 (8)*
H12	0.994 (2)	0.340 (3)	0.452 (2)	0.021 (7)*
H14	1.188 (2)	0.425 (3)	0.254 (2)	0.022 (7)*
H15	1.053 (2)	0.367 (4)	0.090 (2)	0.025 (7)*

	U11	U22	U33	U12	U13	U23
Br	0.01653 (10)	0.02210 (11)	0.02718 (12)	0.00233 (8)	0.00914 (8)	0.00332 (9)
S	0.0167 (2)	0.0152 (2)	0.0142 (2)	0.00039 (18)	0.00489 (17)	0.00036 (18)
C1	0.0145 (8)	0.0160 (9)	0.0190 (9)	0.0025 (7)	0.0067 (7)	0.0034 (8)
C2	0.0158 (9)	0.0182 (10)	0.0211 (10)	−0.0028 (8)	0.0017 (8)	0.0007 (8)
C3	0.0194 (10)	0.0171 (10)	0.0162 (9)	−0.0019 (8)	0.0019 (7)	−0.0031 (8)
C4	0.0148 (8)	0.0161 (9)	0.0145 (9)	0.0012 (7)	0.0045 (7)	0.0014 (7)
C5	0.0154 (9)	0.0139 (9)	0.0190 (10)	−0.0005 (7)	0.0042 (7)	−0.0018 (7)
C6	0.0180 (9)	0.0164 (10)	0.0163 (9)	0.0005 (8)	0.0034 (7)	−0.0015 (8)
O7	0.0228 (8)	0.0173 (7)	0.0239 (8)	−0.0018 (6)	0.0106 (6)	0.0024 (6)
O8	0.0229 (8)	0.0266 (9)	0.0164 (7)	0.0016 (6)	0.0056 (6)	−0.0027 (6)
O9	0.0157 (7)	0.0138 (7)	0.0191 (7)	−0.0006 (5)	0.0029 (5)	−0.0023 (5)
C10	0.0156 (9)	0.0127 (9)	0.0164 (9)	−0.0004 (7)	0.0037 (7)	−0.0001 (7)
C11	0.0150 (9)	0.0167 (9)	0.0204 (10)	0.0005 (8)	0.0070 (8)	0.0037 (8)
C12	0.0183 (9)	0.0163 (9)	0.0169 (9)	0.0016 (8)	0.0055 (8)	0.0035 (8)
C13	0.0150 (9)	0.0137 (9)	0.0172 (9)	0.0014 (7)	0.0028 (7)	−0.0005 (7)
C14	0.0142 (9)	0.0175 (10)	0.0231 (10)	−0.0008 (8)	0.0065 (8)	−0.0008 (8)
C15	0.0183 (9)	0.0180 (10)	0.0187 (10)	−0.0013 (8)	0.0076 (8)	−0.0009 (8)
N16	0.0188 (8)	0.0149 (8)	0.0198 (8)	0.0007 (7)	0.0026 (7)	0.0008 (7)
O17	0.0268 (8)	0.0254 (9)	0.0168 (7)	−0.0015 (7)	0.0039 (6)	−0.0015 (6)
O18	0.0157 (7)	0.0318 (10)	0.0279 (9)	−0.0007 (7)	0.0034 (6)	−0.0010 (7)

Br—C1	1.897 (2)	O9—C10	1.414 (2)
S—O8	1.4239 (16)	C10—C15	1.383 (3)
S—O7	1.4277 (17)	C10—C11	1.384 (3)
S—O9	1.6167 (16)	C11—C12	1.390 (3)
S—C4	1.753 (2)	C11—H11	0.96 (3)
C1—C2	1.388 (3)	C12—C13	1.385 (3)
C1—C6	1.389 (3)	C12—H12	0.95 (3)
C2—C3	1.393 (3)	C13—C14	1.383 (3)
C2—H2	0.96 (3)	C13—N16	1.475 (3)
C3—C4	1.392 (3)	C14—C15	1.393 (3)
C3—H3	0.92 (3)	C14—H14	0.91 (3)
C4—C5	1.389 (3)	C15—H15	0.98 (3)
C5—C6	1.387 (3)	N16—O17	1.225 (2)
C5—H5	0.95 (3)	N16—O18	1.229 (2)
C6—H6	0.93 (3)
O8—S—O7	121.22 (10)	C1—C6—H6	119.2 (17)
O8—S—O9	103.14 (9)	C10—O9—S	119.66 (13)
O7—S—O9	107.73 (9)	C15—C10—C11	123.02 (19)
O8—S—C4	109.96 (10)	C15—C10—O9	118.07 (18)
O7—S—C4	109.35 (10)	C11—C10—O9	118.77 (18)
O9—S—C4	103.88 (9)	C10—C11—C12	118.31 (19)
C2—C1—C6	122.4 (2)	C10—C11—H11	120.7 (18)
C2—C1—Br	120.21 (16)	C12—C11—H11	121.0 (18)
C6—C1—Br	117.42 (16)	C13—C12—C11	118.7 (2)
C1—C2—C3	118.6 (2)	C13—C12—H12	122.0 (17)
C1—C2—H2	122.1 (17)	C11—C12—H12	119.2 (17)
C3—C2—H2	119.2 (17)	C14—C13—C12	122.90 (19)
C4—C3—C2	119.0 (2)	C14—C13—N16	118.82 (18)
C4—C3—H3	120.2 (16)	C12—C13—N16	118.25 (19)
C2—C3—H3	120.8 (16)	C13—C14—C15	118.37 (19)
C5—C4—C3	122.1 (2)	C13—C14—H14	121.6 (18)
C5—C4—S	118.84 (16)	C15—C14—H14	120.1 (18)
C3—C4—S	119.07 (16)	C10—C15—C14	118.6 (2)
C6—C5—C4	118.91 (19)	C10—C15—H15	120.4 (17)
C6—C5—H5	120.2 (17)	C14—C15—H15	120.9 (17)
C4—C5—H5	120.9 (17)	O17—N16—O18	124.18 (19)
C5—C6—C1	119.0 (2)	O17—N16—C13	117.87 (18)
C5—C6—H6	121.8 (17)	O18—N16—C13	117.95 (18)
C6—C1—C2—C3	1.2 (3)	C4—S—O9—C10	−86.54 (16)
Br—C1—C2—C3	−179.34 (16)	S—O9—C10—C15	−91.9 (2)
C1—C2—C3—C4	−2.1 (3)	S—O9—C10—C11	92.2 (2)
C2—C3—C4—C5	0.8 (3)	C15—C10—C11—C12	−0.8 (3)
C2—C3—C4—S	−179.91 (17)	O9—C10—C11—C12	174.83 (19)
O8—S—C4—C5	−168.82 (17)	C10—C11—C12—C13	−1.5 (3)
O7—S—C4—C5	−33.4 (2)	C11—C12—C13—C14	2.5 (3)
O9—S—C4—C5	81.36 (18)	C11—C12—C13—N16	−175.55 (19)
O8—S—C4—C3	11.9 (2)	C12—C13—C14—C15	−1.1 (3)
O7—S—C4—C3	147.24 (17)	N16—C13—C14—C15	176.93 (19)
O9—S—C4—C3	−97.96 (18)	C11—C10—C15—C14	2.2 (3)
C3—C4—C5—C6	1.6 (3)	O9—C10—C15—C14	−173.47 (19)
S—C4—C5—C6	−177.71 (16)	C13—C14—C15—C10	−1.2 (3)
C4—C5—C6—C1	−2.5 (3)	C14—C13—N16—O17	174.0 (2)
C2—C1—C6—C5	1.2 (3)	C12—C13—N16—O17	−7.8 (3)
Br—C1—C6—C5	−178.29 (16)	C14—C13—N16—O18	−6.5 (3)
O8—S—O9—C10	158.70 (15)	C12—C13—N16—O18	171.6 (2)
O7—S—O9—C10	29.39 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O8	0.92 (3)	2.55 (3)	2.930 (3)	105.0 (19)
C11—H11···O8i	0.96 (3)	2.42 (3)	3.288 (3)	150 (2)
C15—H15···O7ii	0.98 (3)	2.42 (3)	3.282 (3)	146 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O8	0.92 (3)	2.55 (3)	2.930 (3)	105.0 (19)
C11—H11⋯O8i	0.96 (3)	2.42 (3)	3.288 (3)	150 (2)
C15—H15⋯O7ii	0.98 (3)	2.42 (3)	3.282 (3)	146 (2)

Symmetry codes: (i) ; (ii) .