p-Phenyl­ene bis­(benzene­sulfonate)

The title structure, C₁₈H₁₄O₆S₂, contains two symmetry-independent conformers. Each conformer resides on a centre of inversion. There are intra- and inter­molecular C—H...O contacts in the structure. The C—S—O—C torsion angles are −66.6 (2) and −70.0 (2)° for the two mol­ecules. The bond lengths are normal.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.043
• wR factor = 0.121
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     -   C4      ..       5.33 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C4     -   C5      ..       6.44 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); 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.

p-Phenylene bis(benzenesulfonate)

Crystal data

C18H14O6S2	Z = 2
Mr = 390.41	F(000) = 404
Triclinic, P1	Dx = 1.423 Mg m^−3
Hall symbol: -P 1	Melting point = 388–389 K
a = 8.225 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.664 (3) Å	Cell parameters from 2006 reflections
c = 12.493 (3) Å	θ = 2.3–22.6°
α = 101.125 (4)°	µ = 0.32 mm^−1
β = 109.046 (4)°	T = 294 K
γ = 110.346 (4)°	Block, colourless
V = 911.3 (4) Å^3	0.40 × 0.34 × 0.20 mm

Data collection

Bruker SMART 1000 diffractometer	3191 independent reflections
Radiation source: fine-focus sealed tube	2346 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −9→9
Tmin = 0.862, Tmax = 0.937	k = −12→6
4642 measured reflections	l = −14→14

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)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.121	w = 1/[σ^2(Fo^2) + (0.0564P)^2 + 0.3203P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.004
3191 reflections	Δρmax = 0.21 e Å^−3
236 parameters	Δρmin = −0.32 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
56 constraints	Extinction coefficient: 0.179 (8)
Primary atom site location: structure-invariant direct methods

Special details

Experimental. IR (KBr): 1381 cm^-1 (O═S═O); ¹H NMR (500 MHz, CDCl₃, δ, p.p.m.): 6.72 (s, 4H), 7.55 (t, J = 8.0 Hz, 4H), 7.70 (t, J = 7.5 Hz, 2H), 7.81 (d, J = 7.0 Hz, 4H).

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	0.02464 (11)	0.98717 (8)	0.79836 (6)	0.0627 (3)
S2	0.39752 (10)	0.64022 (8)	0.32249 (6)	0.0608 (3)
O1	0.2428 (3)	1.09633 (18)	0.88713 (16)	0.0611 (5)
O2	−0.0563 (4)	1.0777 (3)	0.7634 (2)	0.0963 (8)
O3	−0.0533 (3)	0.8953 (3)	0.85588 (19)	0.0841 (7)
O4	0.1719 (2)	0.54401 (19)	0.24340 (16)	0.0580 (5)
O5	0.4517 (3)	0.7681 (2)	0.2965 (2)	0.0824 (6)
O6	0.4199 (3)	0.6432 (3)	0.44020 (18)	0.0849 (7)
C1	0.0422 (3)	0.8883 (3)	0.6770 (2)	0.0508 (6)
C2	−0.0415 (4)	0.7427 (3)	0.6443 (3)	0.0678 (8)
H2	−0.1000	0.6991	0.6882	0.081*
C3	−0.0380 (5)	0.6633 (4)	0.5474 (4)	0.0927 (11)
H3	−0.0965	0.5644	0.5240	0.111*
C4	0.0488 (6)	0.7255 (5)	0.4848 (3)	0.0952 (13)
H4	0.0486	0.6689	0.4179	0.114*
C5	0.1387 (6)	0.8723 (5)	0.5179 (3)	0.0952 (12)
H5	0.2016	0.9142	0.4751	0.114*
C6	0.1341 (4)	0.9567 (3)	0.6162 (3)	0.0701 (8)
H6	0.1911	1.0556	0.6397	0.084*
C7	0.3697 (4)	1.0426 (2)	0.9433 (2)	0.0506 (6)
C8	0.3581 (4)	0.9974 (3)	1.0375 (2)	0.0571 (7)
H8	0.2626	0.9965	1.0621	0.069*
C9	0.4908 (4)	0.9535 (3)	1.0948 (2)	0.0565 (7)
H9	0.4857	0.9218	1.1585	0.068*
C10	0.4988 (4)	0.5378 (3)	0.2687 (2)	0.0557 (7)
C11	0.5723 (4)	0.5687 (4)	0.1873 (3)	0.0761 (9)
H11	0.5698	0.6442	0.1611	0.091*
C12	0.6498 (5)	0.4845 (6)	0.1456 (3)	0.0983 (13)
H12	0.6976	0.5025	0.0893	0.118*
C13	0.6569 (5)	0.3753 (5)	0.1860 (4)	0.0958 (12)
H13	0.7111	0.3206	0.1580	0.115*
C14	0.5847 (5)	0.3461 (4)	0.2673 (3)	0.0821 (10)
H14	0.5893	0.2714	0.2942	0.099*
C15	0.5055 (4)	0.4269 (3)	0.3090 (3)	0.0628 (7)
H15	0.4564	0.4072	0.3643	0.075*
C16	0.0898 (3)	0.5244 (3)	0.1190 (2)	0.0490 (6)
C17	0.0601 (4)	0.6317 (3)	0.0835 (2)	0.0539 (6)
H17	0.1009	0.7196	0.1403	0.065*
C18	−0.0313 (4)	0.6066 (3)	−0.0381 (3)	0.0542 (7)
H18	−0.0529	0.6774	−0.0648	0.065*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0625 (5)	0.0703 (5)	0.0594 (5)	0.0379 (4)	0.0260 (4)	0.0143 (4)
S2	0.0619 (5)	0.0642 (5)	0.0540 (4)	0.0247 (4)	0.0240 (3)	0.0229 (3)
O1	0.0703 (12)	0.0492 (10)	0.0571 (11)	0.0294 (9)	0.0202 (10)	0.0115 (8)
O2	0.1105 (19)	0.1040 (17)	0.0831 (15)	0.0813 (16)	0.0258 (14)	0.0134 (13)
O3	0.0686 (13)	0.1128 (17)	0.0733 (14)	0.0309 (13)	0.0430 (12)	0.0325 (13)
O4	0.0537 (11)	0.0703 (12)	0.0607 (11)	0.0271 (9)	0.0318 (9)	0.0320 (9)
O5	0.0760 (14)	0.0595 (12)	0.0927 (16)	0.0183 (11)	0.0235 (12)	0.0318 (11)
O6	0.1005 (17)	0.1112 (17)	0.0526 (12)	0.0553 (15)	0.0354 (12)	0.0273 (12)
C1	0.0458 (14)	0.0532 (15)	0.0497 (14)	0.0235 (12)	0.0181 (12)	0.0117 (12)
C2	0.0559 (17)	0.0551 (17)	0.085 (2)	0.0228 (14)	0.0286 (16)	0.0143 (15)
C3	0.075 (2)	0.075 (2)	0.104 (3)	0.0336 (19)	0.029 (2)	0.000 (2)
C4	0.089 (3)	0.114 (3)	0.060 (2)	0.059 (3)	0.015 (2)	−0.012 (2)
C5	0.092 (3)	0.151 (4)	0.068 (2)	0.064 (3)	0.048 (2)	0.045 (2)
C6	0.076 (2)	0.0726 (19)	0.0649 (18)	0.0319 (16)	0.0324 (16)	0.0268 (16)
C7	0.0538 (15)	0.0408 (13)	0.0447 (14)	0.0154 (12)	0.0168 (12)	0.0073 (11)
C8	0.0569 (16)	0.0627 (16)	0.0510 (15)	0.0227 (14)	0.0290 (13)	0.0149 (13)
C9	0.0638 (17)	0.0590 (16)	0.0478 (15)	0.0217 (14)	0.0290 (14)	0.0222 (13)
C10	0.0443 (14)	0.0683 (17)	0.0475 (15)	0.0178 (13)	0.0183 (12)	0.0217 (13)
C11	0.0614 (18)	0.105 (2)	0.0680 (19)	0.0298 (18)	0.0360 (16)	0.0418 (18)
C12	0.063 (2)	0.156 (4)	0.072 (2)	0.038 (2)	0.0414 (19)	0.031 (3)
C13	0.062 (2)	0.117 (3)	0.083 (3)	0.038 (2)	0.023 (2)	−0.001 (2)
C14	0.067 (2)	0.074 (2)	0.087 (2)	0.0316 (18)	0.0184 (19)	0.0166 (18)
C15	0.0528 (16)	0.0693 (18)	0.0613 (17)	0.0215 (14)	0.0236 (14)	0.0239 (15)
C16	0.0429 (13)	0.0539 (15)	0.0617 (16)	0.0226 (12)	0.0298 (12)	0.0277 (13)
C17	0.0530 (15)	0.0466 (14)	0.0678 (18)	0.0251 (12)	0.0291 (14)	0.0199 (13)
C18	0.0544 (16)	0.0499 (15)	0.0711 (18)	0.0290 (13)	0.0296 (14)	0.0312 (14)

Geometric parameters (Å, º)

S1—O2	1.409 (2)	C7—C8	1.373 (3)
S1—O3	1.423 (2)	C8—C9	1.377 (4)
S1—O1	1.599 (2)	C8—H8	0.9300
S1—C1	1.750 (3)	C9—C7^i	1.370 (4)
S2—O6	1.414 (2)	C9—H9	0.9300
S2—O5	1.417 (2)	C10—C11	1.379 (4)
S2—O4	1.6001 (19)	C10—C15	1.382 (4)
S2—C10	1.748 (3)	C11—C12	1.386 (5)
O1—C7	1.415 (3)	C11—H11	0.9300
O4—C16	1.417 (3)	C12—C13	1.367 (6)
C1—C2	1.371 (4)	C12—H12	0.9300
C1—C6	1.372 (4)	C13—C14	1.367 (5)
C2—C3	1.351 (5)	C13—H13	0.9300
C2—H2	0.9300	C14—C15	1.370 (4)
C3—C4	1.341 (5)	C14—H14	0.9300
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.384 (6)	C16—C18^ii	1.369 (4)
C4—H4	0.9300	C16—C17	1.373 (3)
C5—C6	1.396 (5)	C17—C18	1.379 (4)
C5—H5	0.9300	C17—H17	0.9300
C6—H6	0.9300	C18—C16^ii	1.369 (4)
C7—C9^i	1.370 (4)	C18—H18	0.9300
O2—S1—O3	119.80 (16)	C8—C7—O1	120.1 (2)
O2—S1—O1	102.82 (13)	C7—C8—C9	118.7 (2)
O3—S1—O1	109.63 (12)	C7—C8—H8	120.6
O2—S1—C1	110.41 (13)	C9—C8—H8	120.6
O3—S1—C1	109.39 (14)	C7^i—C9—C8	119.0 (2)
O1—S1—C1	103.39 (11)	C7^i—C9—H9	120.5
O6—S2—O5	120.76 (15)	C8—C9—H9	120.5
O6—S2—O4	102.61 (12)	C11—C10—C15	120.6 (3)
O5—S2—O4	108.61 (12)	C11—C10—S2	119.8 (2)
O6—S2—C10	110.20 (13)	C15—C10—S2	119.6 (2)
O5—S2—C10	109.64 (14)	C10—C11—C12	118.3 (3)
O4—S2—C10	103.41 (11)	C10—C11—H11	120.8
C7—O1—S1	118.97 (15)	C12—C11—H11	120.8
C16—O4—S2	119.64 (14)	C13—C12—C11	120.8 (3)
C2—C1—C6	122.1 (3)	C13—C12—H12	119.6
C2—C1—S1	117.9 (2)	C11—C12—H12	119.6
C6—C1—S1	120.0 (2)	C14—C13—C12	120.3 (4)
C3—C2—C1	119.3 (3)	C14—C13—H13	119.8
C3—C2—H2	120.4	C12—C13—H13	119.8
C1—C2—H2	120.4	C13—C14—C15	119.9 (4)
C4—C3—C2	120.7 (4)	C13—C14—H14	120.0
C4—C3—H3	119.6	C15—C14—H14	120.0
C2—C3—H3	119.6	C14—C15—C10	119.9 (3)
C3—C4—C5	121.1 (3)	C14—C15—H15	120.0
C3—C4—H4	119.4	C10—C15—H15	120.0
C5—C4—H4	119.4	C18^ii—C16—C17	122.4 (2)
C4—C5—C6	119.3 (3)	C18^ii—C16—O4	117.6 (2)
C4—C5—H5	120.4	C17—C16—O4	119.9 (2)
C6—C5—H5	120.4	C16—C17—C18	118.7 (2)
C1—C6—C5	117.5 (3)	C16—C17—H17	120.6
C1—C6—H6	121.2	C18—C17—H17	120.6
C5—C6—H6	121.2	C16^ii—C18—C17	118.9 (2)
C9^i—C7—C8	122.3 (2)	C16^ii—C18—H18	120.5
C9^i—C7—O1	117.5 (2)	C17—C18—H18	120.5
O2—S1—O1—C7	178.48 (18)	C9^i—C7—C8—C9	−0.5 (4)
O3—S1—O1—C7	50.0 (2)	O1—C7—C8—C9	−176.3 (2)
C1—S1—O1—C7	−66.6 (2)	C7—C8—C9—C7^i	0.5 (4)
O6—S2—O4—C16	175.39 (19)	O6—S2—C10—C11	−150.7 (2)
O5—S2—O4—C16	46.5 (2)	O5—S2—C10—C11	−15.4 (3)
C10—S2—O4—C16	−70.0 (2)	O4—S2—C10—C11	100.2 (2)
O2—S1—C1—C2	−124.9 (2)	O6—S2—C10—C15	28.9 (3)
O3—S1—C1—C2	8.9 (3)	O5—S2—C10—C15	164.2 (2)
O1—S1—C1—C2	125.7 (2)	O4—S2—C10—C15	−80.1 (2)
O2—S1—C1—C6	53.7 (3)	C15—C10—C11—C12	1.0 (4)
O3—S1—C1—C6	−172.5 (2)	S2—C10—C11—C12	−179.4 (2)
O1—S1—C1—C6	−55.7 (2)	C10—C11—C12—C13	−1.3 (5)
C6—C1—C2—C3	−1.6 (4)	C11—C12—C13—C14	1.0 (6)
S1—C1—C2—C3	176.9 (2)	C12—C13—C14—C15	−0.3 (5)
C1—C2—C3—C4	1.1 (5)	C13—C14—C15—C10	0.0 (5)
C2—C3—C4—C5	0.6 (6)	C11—C10—C15—C14	−0.4 (4)
C3—C4—C5—C6	−1.8 (6)	S2—C10—C15—C14	180.0 (2)
C2—C1—C6—C5	0.4 (4)	S2—O4—C16—C18^ii	107.8 (2)
S1—C1—C6—C5	−178.1 (2)	S2—O4—C16—C17	−76.4 (3)
C4—C5—C6—C1	1.3 (5)	C18^ii—C16—C17—C18	−0.2 (4)
S1—O1—C7—C9^i	109.3 (2)	O4—C16—C17—C18	−175.8 (2)
S1—O1—C7—C8	−74.8 (3)	C16—C17—C18—C16^ii	0.2 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3	0.93	2.48	2.875 (4)	106
C11—H11···O5	0.93	2.58	2.932 (4)	103
C17—H17···O2^iii	0.93	2.47	3.329 (5)	154
C15—H15···O6^iv	0.93	2.56	3.274 (5)	134

Symmetry codes: (iii) −x, −y+2, −z+1; (iv) −x+1, −y+1, −z+1.