The title molecule, C
18H
14O
6S
2, 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.
Supporting information
CCDC reference: 289686
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C)= 0.003 Å
- R factor = 0.036
- wR factor = 0.093
- Data-to-parameter ratio = 15.2
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
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)
top
Crystal data top
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) Å3 | Block, colorless |
Z = 4 | 0.34 × 0.30 × 0.14 mm |
Data collection top
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 top
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)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.0372P)2 + 0.6051P] where P = (Fo2 + 2Fc2)/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+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.071 (2) |
Special details top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16···O2i | 0.93 | 2.55 | 3.418 (3) | 156 |
C11—H11···O1ii | 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. |