o-Phenyl­ene bis­(benzene­sulfonate)

The title mol­ecule, C₁₈H₁₄O₆S₂, adopts an asymmetric conformation with alternating benzene rings and sulfonate groups. In the crystal structure there are two independent C—H...O hydrogen bonds, connecting the mol­ecules into a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.036
• wR factor = 0.093
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

o-Phenylene bis(benzenesulfonate)

Crystal data

C18H14O6S2	F(000) = 808
Mr = 390.41	Dx = 1.475 Mg m^−3
Monoclinic, P21/n	Melting point: 390.41 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.8805 (12) Å	Cell parameters from 4019 reflections
b = 14.404 (2) Å	θ = 2.8–26.4°
c = 13.754 (2) Å	µ = 0.34 mm^−1
β = 92.423 (2)°	T = 294 K
V = 1757.9 (4) Å^3	Block, colorless
Z = 4	0.34 × 0.30 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3596 independent reflections
Radiation source: fine-focus sealed tube	2792 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
φ and ω scans	θmax = 26.4°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −11→5
Tmin = 0.865, Tmax = 0.954	k = −18→17
9780 measured reflections	l = −16→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.093	w = 1/[σ^2(Fo^2) + (0.0372P)^2 + 0.6051P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.005
3596 reflections	Δρmax = 0.30 e Å^−3
236 parameters	Δρmin = −0.36 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.071 (2)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.16151 (5)	0.18756 (3)	0.84590 (3)	0.03694 (15)
S2	0.09062 (6)	0.33667 (4)	1.12319 (4)	0.04733 (17)
O1	0.06321 (17)	0.25986 (9)	0.81349 (10)	0.0526 (4)
O2	0.31485 (15)	0.20622 (11)	0.87160 (10)	0.0502 (4)
O3	0.08191 (13)	0.14643 (9)	0.93960 (9)	0.0395 (3)
O4	0.20919 (14)	0.27526 (9)	1.06542 (9)	0.0411 (3)
O5	0.1174 (2)	0.42780 (10)	1.08836 (15)	0.0730 (5)
O6	0.10913 (18)	0.31687 (12)	1.22400 (11)	0.0644 (5)
C1	0.1484 (2)	0.09518 (12)	0.76302 (13)	0.0369 (4)
C2	0.0156 (3)	0.08153 (16)	0.70913 (17)	0.0563 (6)
H2	−0.0668	0.1202	0.7174	0.068*
C3	0.0068 (3)	0.00983 (18)	0.64302 (19)	0.0715 (8)
H3	−0.0823	−0.0005	0.6067	0.086*
C4	0.1290 (3)	−0.04638 (17)	0.63060 (19)	0.0678 (7)
H4	0.1224	−0.0946	0.5857	0.081*
C5	0.2605 (3)	−0.03213 (17)	0.6836 (2)	0.0661 (7)
H5	0.3429	−0.0705	0.6745	0.079*
C6	0.2716 (2)	0.03916 (15)	0.75087 (17)	0.0514 (5)
H6	0.3608	0.0491	0.7872	0.062*
C7	0.1704 (2)	0.11629 (13)	1.02053 (13)	0.0348 (4)
C8	0.1934 (2)	0.02266 (14)	1.03536 (16)	0.0502 (5)
H8	0.1579	−0.0203	0.9894	0.060*
C9	0.2699 (3)	−0.00638 (16)	1.11930 (18)	0.0622 (6)
H9	0.2856	−0.0694	1.1303	0.075*
C10	0.3229 (3)	0.05710 (18)	1.18643 (18)	0.0613 (6)
H10	0.3735	0.0367	1.2430	0.074*
C11	0.3021 (2)	0.15104 (16)	1.17116 (15)	0.0496 (5)
H11	0.3393	0.1939	1.2167	0.059*
C12	0.2255 (2)	0.18029 (12)	1.08762 (14)	0.0354 (4)
C13	−0.0846 (2)	0.29605 (13)	1.07870 (14)	0.0402 (4)
C14	−0.1547 (2)	0.22553 (15)	1.12723 (16)	0.0485 (5)
H14	−0.1105	0.2004	1.1838	0.058*
C15	−0.2916 (3)	0.19283 (17)	1.0903 (2)	0.0627 (6)
H15	−0.3408	0.1458	1.1227	0.075*
C16	−0.3552 (3)	0.2292 (2)	1.0066 (2)	0.0729 (8)
H16	−0.4476	0.2068	0.9823	0.088*
C17	−0.2838 (3)	0.2989 (2)	0.9579 (2)	0.0725 (8)
H17	−0.3275	0.3225	0.9004	0.087*
C18	−0.1474 (3)	0.33400 (16)	0.99374 (17)	0.0566 (6)
H18	−0.0993	0.3817	0.9617	0.068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0394 (3)	0.0361 (3)	0.0347 (3)	−0.00246 (19)	−0.00483 (18)	0.00036 (19)
S2	0.0453 (3)	0.0400 (3)	0.0562 (4)	−0.0034 (2)	−0.0041 (2)	−0.0154 (2)
O1	0.0692 (10)	0.0369 (8)	0.0506 (9)	0.0102 (7)	−0.0100 (7)	0.0015 (6)
O2	0.0417 (8)	0.0637 (9)	0.0451 (8)	−0.0156 (7)	−0.0011 (6)	−0.0021 (7)
O3	0.0322 (7)	0.0525 (8)	0.0333 (7)	−0.0041 (6)	−0.0050 (5)	0.0012 (6)
O4	0.0396 (7)	0.0355 (7)	0.0479 (8)	−0.0048 (5)	0.0000 (6)	−0.0020 (6)
O5	0.0714 (11)	0.0323 (8)	0.1151 (15)	−0.0082 (7)	0.0019 (10)	−0.0106 (8)
O6	0.0601 (10)	0.0852 (12)	0.0469 (9)	0.0006 (8)	−0.0089 (7)	−0.0261 (8)
C1	0.0413 (10)	0.0348 (10)	0.0343 (10)	−0.0005 (8)	−0.0008 (8)	0.0015 (7)
C2	0.0519 (13)	0.0565 (14)	0.0590 (15)	0.0087 (10)	−0.0167 (11)	−0.0162 (11)
C3	0.0756 (18)	0.0651 (16)	0.0713 (17)	0.0006 (13)	−0.0250 (14)	−0.0227 (13)
C4	0.093 (2)	0.0488 (14)	0.0619 (16)	−0.0049 (13)	0.0030 (14)	−0.0188 (12)
C5	0.0686 (17)	0.0472 (13)	0.0836 (19)	0.0127 (11)	0.0152 (14)	−0.0092 (12)
C6	0.0449 (12)	0.0469 (12)	0.0623 (14)	0.0056 (9)	0.0008 (10)	−0.0040 (10)
C7	0.0313 (9)	0.0381 (10)	0.0346 (10)	−0.0019 (7)	−0.0025 (7)	0.0028 (8)
C8	0.0559 (13)	0.0391 (11)	0.0554 (14)	−0.0025 (9)	0.0009 (10)	−0.0028 (9)
C9	0.0734 (17)	0.0439 (13)	0.0689 (17)	0.0110 (11)	−0.0010 (13)	0.0148 (12)
C10	0.0615 (15)	0.0704 (16)	0.0509 (14)	0.0130 (12)	−0.0123 (11)	0.0163 (12)
C11	0.0445 (12)	0.0617 (14)	0.0414 (12)	−0.0010 (10)	−0.0121 (9)	−0.0015 (10)
C12	0.0306 (9)	0.0355 (10)	0.0398 (10)	−0.0016 (7)	−0.0022 (7)	0.0005 (8)
C13	0.0385 (10)	0.0395 (10)	0.0424 (11)	0.0050 (8)	−0.0008 (8)	−0.0092 (8)
C14	0.0486 (12)	0.0493 (12)	0.0477 (12)	−0.0002 (9)	0.0026 (9)	−0.0050 (9)
C15	0.0484 (13)	0.0637 (15)	0.0765 (18)	−0.0114 (11)	0.0077 (12)	−0.0120 (13)
C16	0.0400 (13)	0.088 (2)	0.090 (2)	0.0019 (13)	−0.0095 (13)	−0.0276 (16)
C17	0.0608 (16)	0.092 (2)	0.0622 (17)	0.0257 (15)	−0.0210 (13)	−0.0077 (15)
C18	0.0564 (14)	0.0545 (14)	0.0582 (14)	0.0092 (10)	−0.0046 (11)	0.0064 (11)

Geometric parameters (Å, º)

S1—O2	1.4180 (14)	C7—C8	1.378 (3)
S1—O1	1.4187 (14)	C7—C12	1.379 (3)
S1—O3	1.6089 (13)	C8—C9	1.380 (3)
S1—C1	1.7529 (19)	C8—H8	0.930
S2—O6	1.4184 (17)	C9—C10	1.369 (3)
S2—O5	1.4209 (17)	C9—H9	0.930
S2—O4	1.6103 (14)	C10—C11	1.381 (3)
S2—C13	1.7488 (19)	C10—H10	0.930
O3—C7	1.404 (2)	C11—C12	1.376 (3)
O4—C12	1.408 (2)	C11—H11	0.930
C1—C6	1.375 (3)	C13—C14	1.378 (3)
C1—C2	1.380 (3)	C13—C18	1.386 (3)
C2—C3	1.376 (3)	C14—C15	1.380 (3)
C2—H2	0.930	C14—H14	0.930
C3—C4	1.371 (4)	C15—C16	1.366 (4)
C3—H3	0.930	C15—H15	0.930
C4—C5	1.366 (4)	C16—C17	1.376 (4)
C4—H4	0.930	C16—H16	0.930
C5—C6	1.383 (3)	C17—C18	1.384 (3)
C5—H5	0.930	C17—H17	0.930
C6—H6	0.930	C18—H18	0.930
O2—S1—O1	120.72 (9)	C12—C7—O3	119.65 (16)
O2—S1—O3	108.66 (8)	C7—C8—C9	119.0 (2)
O1—S1—O3	103.69 (8)	C7—C8—H8	120.5
O2—S1—C1	110.04 (9)	C9—C8—H8	120.5
O1—S1—C1	109.26 (9)	C10—C9—C8	120.3 (2)
O3—S1—C1	102.83 (8)	C10—C9—H9	119.8
O6—S2—O5	120.08 (11)	C8—C9—H9	119.8
O6—S2—O4	108.71 (9)	C9—C10—C11	120.8 (2)
O5—S2—O4	102.63 (10)	C9—C10—H10	119.6
O6—S2—C13	109.84 (10)	C11—C10—H10	119.6
O5—S2—C13	110.51 (10)	C12—C11—C10	119.0 (2)
O4—S2—C13	103.55 (8)	C12—C11—H11	120.5
C7—O3—S1	119.93 (11)	C10—C11—H11	120.5
C12—O4—S2	119.34 (12)	C11—C12—C7	120.19 (18)
C6—C1—C2	121.15 (19)	C11—C12—O4	121.40 (16)
C6—C1—S1	119.55 (15)	C7—C12—O4	118.30 (16)
C2—C1—S1	119.28 (15)	C14—C13—C18	121.7 (2)
C3—C2—C1	119.0 (2)	C14—C13—S2	119.36 (15)
C3—C2—H2	120.5	C18—C13—S2	118.93 (17)
C1—C2—H2	120.5	C13—C14—C15	118.8 (2)
C4—C3—C2	120.2 (2)	C13—C14—H14	120.6
C4—C3—H3	119.9	C15—C14—H14	120.6
C2—C3—H3	119.9	C16—C15—C14	120.4 (2)
C5—C4—C3	120.6 (2)	C16—C15—H15	119.8
C5—C4—H4	119.7	C14—C15—H15	119.8
C3—C4—H4	119.7	C15—C16—C17	120.5 (2)
C4—C5—C6	120.3 (2)	C15—C16—H16	119.7
C4—C5—H5	119.9	C17—C16—H16	119.7
C6—C5—H5	119.9	C16—C17—C18	120.5 (2)
C1—C6—C5	118.8 (2)	C16—C17—H17	119.7
C1—C6—H6	120.6	C18—C17—H17	119.7
C5—C6—H6	120.6	C17—C18—C13	118.1 (2)
C8—C7—C12	120.59 (17)	C17—C18—H18	120.9
C8—C7—O3	119.64 (17)	C13—C18—H18	120.9
O2—S1—O3—C7	−13.63 (16)	C8—C9—C10—C11	−0.6 (4)
O1—S1—O3—C7	−143.21 (13)	C9—C10—C11—C12	0.7 (4)
C1—S1—O3—C7	102.97 (14)	C10—C11—C12—C7	0.1 (3)
O6—S2—O4—C12	46.22 (15)	C10—C11—C12—O4	−175.98 (19)
O5—S2—O4—C12	174.41 (13)	C8—C7—C12—C11	−1.1 (3)
C13—S2—O4—C12	−70.54 (14)	O3—C7—C12—C11	174.81 (18)
O2—S1—C1—C6	15.40 (19)	C8—C7—C12—O4	175.09 (17)
O1—S1—C1—C6	150.11 (17)	O3—C7—C12—O4	−9.0 (3)
O3—S1—C1—C6	−100.22 (17)	S2—O4—C12—C11	−75.3 (2)
O2—S1—C1—C2	−162.87 (17)	S2—O4—C12—C7	108.53 (17)
O1—S1—C1—C2	−28.2 (2)	O6—S2—C13—C14	−23.45 (19)
O3—S1—C1—C2	81.51 (18)	O5—S2—C13—C14	−158.19 (16)
C6—C1—C2—C3	0.7 (4)	O4—S2—C13—C14	92.51 (17)
S1—C1—C2—C3	178.9 (2)	O6—S2—C13—C18	158.38 (17)
C1—C2—C3—C4	−0.6 (4)	O5—S2—C13—C18	23.6 (2)
C2—C3—C4—C5	0.2 (4)	O4—S2—C13—C18	−85.66 (17)
C3—C4—C5—C6	0.2 (4)	C18—C13—C14—C15	−0.6 (3)
C2—C1—C6—C5	−0.3 (3)	S2—C13—C14—C15	−178.75 (16)
S1—C1—C6—C5	−178.57 (18)	C13—C14—C15—C16	0.7 (3)
C4—C5—C6—C1	−0.1 (4)	C14—C15—C16—C17	0.0 (4)
S1—O3—C7—C8	−102.62 (18)	C15—C16—C17—C18	−0.9 (4)
S1—O3—C7—C12	81.4 (2)	C16—C17—C18—C13	1.0 (4)
C12—C7—C8—C9	1.3 (3)	C14—C13—C18—C17	−0.2 (3)
O3—C7—C8—C9	−174.67 (19)	S2—C13—C18—C17	177.89 (18)
C7—C8—C9—C10	−0.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O2^i	0.93	2.55	3.418 (3)	156
C11—H11···O1^ii	0.93	2.44	3.236 (3)	144

Symmetry codes: (i) x−1, y, z; (ii) x+1/2, −y+1/2, z+1/2.