Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021216/kp2097sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021216/kp2097Isup2.hkl |
CCDC reference: 651414
The title compound (I), was prepared by the hydrothermal reaction of Mn(OAc)2.4H2O(0.050 g, 0.20 mmol), 4,4'-sulfonyldibenzoic acid (0.062 g, 0.20 mmol) and in water (8 ml). The reaction was performed in 23 ml Teflon-lined stainless steel Parr bombs under autogeneous pressure. After heating at 423 K for 3 days and cooling to room temperature at 5 K h-1, green crystals of (I) were obtained.
The H atoms were positioned geometrically with C—H = 0.93 Å; they were constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq.
Recently, the design and synthesis of the metal-organic frameworks (MOFs) have led to a large number of coordination polymers (Moulton et al., 2001; Kitagawa et al., 2004; Yaghi et al., 2003). 4,4'-sulfonyldibenzoic acid is a typical V-shaped dicarboxylate ligand, which is important in construction of some novel frameworks (Jin et al., 2006; Chen et al., 2002). Here we report the crystal structure of (I) (Fig. 1). The central atom S1 has a tetrahedral arrangement, with the S1—O3=1.4353 (17) Å, S1—O4=1.4405 (18) Å. The atoms S1,O3 and O4 are located at the special position on the mirror plane (x,1/4 - y,z) and the molecular symmetry is Cm. An intermolecular O1—H1A···O2 hydrogen bond connects molecules into a infinite zigzag chain (Fig. 2).
For related literature, see: Chen & Lin (2002); Kitagawa & Kitaura (2004); Moulton & Zaworotko (2001); Fujita et al. (1994).
Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
C14H10O6S | F(000) = 316 |
Mr = 306.29 | Dx = 1.602 Mg m−3 |
Monoclinic, P21/m | Mo Kα radiation, λ = 0.71073 Å |
a = 5.0019 (4) Å | Cell parameters from 1385 reflections |
b = 23.3653 (17) Å | θ = 2.6–27.5° |
c = 5.7871 (5) Å | µ = 0.28 mm−1 |
β = 110.151 (3)° | T = 293 K |
V = 634.94 (9) Å3 | Prism, white |
Z = 2 | 0.21 × 0.13 × 0.10 mm |
Mercury CCD diffractometer | 1493 independent reflections |
Radiation source: fine-focus sealed tube | 1287 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
Detector resolution: 14.6306 pixels mm-1 | θmax = 27.5°, θmin = 3.5° |
CCD_Profile_fitting scans | h = −6→6 |
Absorption correction: multi-scan PROGRAM? (Reference?) | k = −30→28 |
Tmin = 0.943, Tmax = 0.972 | l = −6→7 |
4922 measured reflections |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 1.13 | w = 1/[σ2(Fo2) + (0.0437P)2 + 0.2393P] where P = (Fo2 + 2Fc2)/3 |
1493 reflections | (Δ/σ)max < 0.001 |
100 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.36 e Å−3 |
C14H10O6S | V = 634.94 (9) Å3 |
Mr = 306.29 | Z = 2 |
Monoclinic, P21/m | Mo Kα radiation |
a = 5.0019 (4) Å | µ = 0.28 mm−1 |
b = 23.3653 (17) Å | T = 293 K |
c = 5.7871 (5) Å | 0.21 × 0.13 × 0.10 mm |
β = 110.151 (3)° |
Mercury CCD diffractometer | 1493 independent reflections |
Absorption correction: multi-scan PROGRAM? (Reference?) | 1287 reflections with I > 2σ(I) |
Tmin = 0.943, Tmax = 0.972 | Rint = 0.023 |
4922 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 1.13 | Δρmax = 0.27 e Å−3 |
1493 reflections | Δρmin = −0.36 e Å−3 |
100 parameters |
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 | 1.01179 (12) | 0.2500 | 0.38263 (11) | 0.02846 (19) | |
O1 | 0.0581 (3) | 0.04204 (6) | 0.2645 (3) | 0.0538 (4) | |
C1 | 0.2637 (4) | 0.05520 (7) | 0.4617 (3) | 0.0349 (4) | |
O2 | 0.3019 (3) | 0.03297 (6) | 0.6669 (3) | 0.0519 (4) | |
C2 | 0.4609 (4) | 0.10079 (7) | 0.4376 (3) | 0.0304 (4) | |
O3 | 1.2667 (4) | 0.2500 | 0.5955 (3) | 0.0379 (4) | |
C3 | 0.6752 (4) | 0.12019 (7) | 0.6472 (3) | 0.0347 (4) | |
H3 | 0.7043 | 0.1027 | 0.7982 | 0.042* | |
O4 | 1.0291 (4) | 0.2500 | 0.1392 (3) | 0.0380 (4) | |
C4 | 0.8453 (4) | 0.16565 (7) | 0.6310 (3) | 0.0331 (4) | |
H4 | 0.9868 | 0.1794 | 0.7709 | 0.040* | |
C5 | 0.8018 (3) | 0.19037 (6) | 0.4031 (3) | 0.0270 (4) | |
C6 | 0.5925 (4) | 0.17070 (7) | 0.1919 (3) | 0.0335 (4) | |
H6 | 0.5664 | 0.1876 | 0.0403 | 0.040* | |
C7 | 0.4233 (4) | 0.12549 (8) | 0.2107 (3) | 0.0353 (4) | |
H7 | 0.2832 | 0.1115 | 0.0703 | 0.042* | |
H1A | −0.0784 | 0.0181 | 0.2769 | 0.042* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0256 (3) | 0.0241 (3) | 0.0379 (4) | 0.000 | 0.0138 (3) | 0.000 |
O1 | 0.0453 (8) | 0.0515 (9) | 0.0588 (10) | −0.0231 (7) | 0.0107 (7) | 0.0021 (7) |
C1 | 0.0328 (9) | 0.0277 (8) | 0.0449 (10) | −0.0010 (7) | 0.0145 (8) | 0.0008 (7) |
O2 | 0.0531 (9) | 0.0486 (8) | 0.0536 (9) | −0.0156 (7) | 0.0179 (7) | 0.0098 (7) |
C2 | 0.0296 (9) | 0.0238 (8) | 0.0394 (10) | 0.0003 (6) | 0.0138 (8) | −0.0002 (7) |
O3 | 0.0255 (9) | 0.0354 (9) | 0.0481 (11) | 0.000 | 0.0068 (8) | 0.000 |
C3 | 0.0388 (10) | 0.0313 (9) | 0.0344 (9) | −0.0030 (7) | 0.0132 (8) | 0.0038 (7) |
O4 | 0.0439 (11) | 0.0353 (9) | 0.0435 (11) | 0.000 | 0.0262 (9) | 0.000 |
C4 | 0.0329 (9) | 0.0314 (8) | 0.0319 (9) | −0.0038 (7) | 0.0071 (7) | −0.0005 (7) |
C5 | 0.0251 (8) | 0.0225 (7) | 0.0347 (9) | 0.0014 (6) | 0.0119 (7) | −0.0004 (6) |
C6 | 0.0356 (10) | 0.0324 (9) | 0.0317 (9) | −0.0012 (7) | 0.0104 (8) | 0.0024 (7) |
C7 | 0.0331 (9) | 0.0326 (9) | 0.0353 (9) | −0.0050 (7) | 0.0054 (8) | −0.0020 (7) |
S1—O3 | 1.4357 (18) | C2—C3 | 1.389 (2) |
S1—O4 | 1.4409 (19) | C3—C4 | 1.384 (2) |
S1—C5i | 1.7732 (16) | C3—H3 | 0.9300 |
S1—C5 | 1.7732 (16) | C4—C5 | 1.386 (2) |
O1—C1 | 1.283 (2) | C4—H4 | 0.9300 |
O1—H1A | 0.9040 | C5—C6 | 1.386 (2) |
C1—O2 | 1.249 (2) | C6—C7 | 1.381 (2) |
C1—C2 | 1.490 (2) | C6—H6 | 0.9300 |
C2—C7 | 1.386 (2) | C7—H7 | 0.9300 |
O3—S1—O4 | 120.27 (12) | C4—C3—H3 | 120.0 |
O3—S1—C5i | 108.31 (7) | C2—C3—H3 | 120.0 |
O4—S1—C5i | 107.57 (7) | C3—C4—C5 | 119.04 (16) |
O3—S1—C5 | 108.31 (7) | C3—C4—H4 | 120.5 |
O4—S1—C5 | 107.57 (7) | C5—C4—H4 | 120.5 |
C5i—S1—C5 | 103.59 (10) | C6—C5—C4 | 121.61 (15) |
C1—O1—H1A | 118.3 | C6—C5—S1 | 119.12 (13) |
O2—C1—O1 | 123.98 (16) | C4—C5—S1 | 119.24 (13) |
O2—C1—C2 | 119.79 (16) | C7—C6—C5 | 118.80 (16) |
O1—C1—C2 | 116.22 (16) | C7—C6—H6 | 120.6 |
C7—C2—C3 | 120.21 (16) | C5—C6—H6 | 120.6 |
C7—C2—C1 | 120.51 (16) | C6—C7—C2 | 120.39 (16) |
C3—C2—C1 | 119.21 (16) | C6—C7—H7 | 119.8 |
C4—C3—C2 | 119.91 (16) | C2—C7—H7 | 119.8 |
Symmetry code: (i) x, −y+1/2, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O2ii | 0.90 | 1.74 | 2.6390 (19) | 172 |
Symmetry code: (ii) −x, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C14H10O6S |
Mr | 306.29 |
Crystal system, space group | Monoclinic, P21/m |
Temperature (K) | 293 |
a, b, c (Å) | 5.0019 (4), 23.3653 (17), 5.7871 (5) |
β (°) | 110.151 (3) |
V (Å3) | 634.94 (9) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.28 |
Crystal size (mm) | 0.21 × 0.13 × 0.10 |
Data collection | |
Diffractometer | Mercury CCD |
Absorption correction | Multi-scan PROGRAM? (Reference?) |
Tmin, Tmax | 0.943, 0.972 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4922, 1493, 1287 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.104, 1.13 |
No. of reflections | 1493 |
No. of parameters | 100 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.36 |
Computer programs: CrystalClear (Rigaku, 2000), CrystalClear, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O2i | 0.90 | 1.74 | 2.6390 (19) | 171.8 |
Symmetry code: (i) −x, −y, −z+1. |
Recently, the design and synthesis of the metal-organic frameworks (MOFs) have led to a large number of coordination polymers (Moulton et al., 2001; Kitagawa et al., 2004; Yaghi et al., 2003). 4,4'-sulfonyldibenzoic acid is a typical V-shaped dicarboxylate ligand, which is important in construction of some novel frameworks (Jin et al., 2006; Chen et al., 2002). Here we report the crystal structure of (I) (Fig. 1). The central atom S1 has a tetrahedral arrangement, with the S1—O3=1.4353 (17) Å, S1—O4=1.4405 (18) Å. The atoms S1,O3 and O4 are located at the special position on the mirror plane (x,1/4 - y,z) and the molecular symmetry is Cm. An intermolecular O1—H1A···O2 hydrogen bond connects molecules into a infinite zigzag chain (Fig. 2).