Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100001578/da1102sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100001578/da1102Isup2.hkl |
CCDC reference: 145522
meso-2,3-Diphenylsuccinic acid (182 mg, 0.673 mmol), synthesized according to the method of Wawzonek (1940), was added to solution of Ca(OH)2 (50 mg, 0.673 mmol) in water (100 ml). Slow evaporation of the water produced satisfactory crystals of (I).
Phenyl H atoms were refined with a riding model. All other H atoms were refined with a free variable to restrain H—O and H—H distances.
Data collection: CAD-4 ARGUS (Enraf-Nonius, 1994); cell refinement: CAD-4 ARGUS; data reduction: CHI90S (Boyle, 1997); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Siemens, 1994).
[Ca(C16H12O4)(H2O)6]·H2O | Z = 2 |
Mr = 434.45 | F(000) = 460 |
Triclinic, P1 | Dx = 1.420 Mg m−3 |
a = 6.2394 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.6342 (8) Å | Cell parameters from 25 reflections |
c = 14.1648 (12) Å | θ = 15–16° |
α = 89.697 (7)° | µ = 0.36 mm−1 |
β = 88.440 (9)° | T = 293 K |
γ = 81.320 (8)° | Plate-like, colorless |
V = 1016.1 (2) Å3 | 0.42 × 0.40 × 0.15 mm |
Enraf-Nonius CAD-4 diffractometer | 3307 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.010 |
Graphite monochromator | θmax = 25.0°, θmin = 2.3° |
θ/2θ scans | h = −7→0 |
Absorption correction: ψ-scan (North et al., 1968) | k = −13→13 |
Tmin = 0.922, Tmax = 0.947 | l = −16→16 |
3939 measured reflections | 3 standard reflections every 200 reflections |
3580 independent reflections | intensity decay: none |
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)] = 0.032 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.083 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Calculated w = 1/[σ2(Fo2) + (0.0345P)2 + 0.5761P] where P = (Fo2 + 2Fc2)/3 |
3580 reflections | (Δ/σ)max = −0.001 |
305 parameters | Δρmax = 0.32 e Å−3 |
27 restraints | Δρmin = −0.21 e Å−3 |
[Ca(C16H12O4)(H2O)6]·H2O | γ = 81.320 (8)° |
Mr = 434.45 | V = 1016.1 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.2394 (8) Å | Mo Kα radiation |
b = 11.6342 (8) Å | µ = 0.36 mm−1 |
c = 14.1648 (12) Å | T = 293 K |
α = 89.697 (7)° | 0.42 × 0.40 × 0.15 mm |
β = 88.440 (9)° |
Enraf-Nonius CAD-4 diffractometer | 3307 reflections with I > 2σ(I) |
Absorption correction: ψ-scan (North et al., 1968) | Rint = 0.010 |
Tmin = 0.922, Tmax = 0.947 | 3 standard reflections every 200 reflections |
3939 measured reflections | intensity decay: none |
3580 independent reflections |
R[F2 > 2σ(F2)] = 0.032 | 27 restraints |
wR(F2) = 0.083 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.32 e Å−3 |
3580 reflections | Δρmin = −0.21 e Å−3 |
305 parameters |
Experimental. North A·C·T., Phillips D·C. & Mathews F·S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 7. Theta correction was applied. Weighted transmission curves were used. No Fourier smoothing was applied. |
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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating R_factor_obs 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 | Occ. (<1) | |
Ca | 0.37991 (5) | 0.47407 (3) | 0.36167 (2) | 0.02282 (11) | |
O1 | 0.2858 (2) | 0.53681 (11) | 0.53998 (9) | 0.0273 (3) | |
H11 | 0.201 (3) | 0.4974 (16) | 0.5640 (14) | 0.033* | |
H12 | 0.221 (3) | 0.6022 (16) | 0.5413 (14) | 0.033* | |
O2 | 0.3643 (2) | 0.29612 (11) | 0.45747 (9) | 0.0301 (3) | |
H21 | 0.454 (3) | 0.2439 (17) | 0.4399 (15) | 0.036* | |
H22 | 0.250 (3) | 0.2711 (18) | 0.4574 (15) | 0.036* | |
O3 | 0.4686 (2) | 0.66553 (11) | 0.37107 (10) | 0.0363 (3) | |
H31 | 0.517 (4) | 0.6937 (19) | 0.4153 (14) | 0.044* | |
H32 | 0.445 (4) | 0.7134 (19) | 0.3335 (14) | 0.044* | |
O4 | 0.0164 (2) | 0.59266 (12) | 0.37396 (9) | 0.0323 (3) | |
H41 | −0.046 (3) | 0.6081 (18) | 0.3242 (14) | 0.039* | |
H42 | 0.021 (4) | 0.6506 (17) | 0.3990 (14) | 0.039* | |
O5 | 0.6662 (2) | 0.32689 (13) | 0.28615 (10) | 0.0416 (3) | |
H51 | 0.686 (4) | 0.2639 (19) | 0.3128 (15) | 0.050* | |
H52 | 0.639 (4) | 0.315 (2) | 0.2352 (14) | 0.050* | |
O6 | 0.1447 (2) | 0.36844 (14) | 0.27377 (10) | 0.0434 (4) | |
H61 | 0.138 (4) | 0.399 (2) | 0.2215 (15) | 0.052* | |
H62 | 0.035 (4) | 0.351 (2) | 0.2846 (17) | 0.052* | |
O7 | 0.4400 (2) | 0.53731 (11) | 0.20218 (8) | 0.0330 (3) | |
C1 | 0.3591 (3) | 0.52495 (15) | 0.12349 (12) | 0.0279 (4) | |
O8 | 0.1779 (2) | 0.49517 (13) | 0.11197 (9) | 0.0401 (3) | |
C2 | 0.4933 (3) | 0.5502 (2) | 0.03496 (12) | 0.0315 (4) | |
H2A | 0.6407 | 0.5561 | 0.05444 | 0.038* | |
C3 | 0.3991 (3) | 0.6655 (2) | −0.01053 (13) | 0.0348 (4) | |
C4 | 0.1878 (3) | 0.6888 (2) | −0.04200 (15) | 0.0440 (5) | |
H4A | 0.0974 | 0.6323 | −0.03646 | 0.053* | |
C5 | 0.1115 (4) | 0.7957 (2) | −0.0815 (2) | 0.0584 (6) | |
H5A | −0.0304 | 0.8110 | −0.1019 | 0.070* | |
C6 | 0.2447 (5) | 0.8795 (2) | −0.0908 (2) | 0.0681 (8) | |
H6A | 0.1928 | 0.9517 | −0.1167 | 0.082* | |
C7 | 0.4537 (5) | 0.8557 (2) | −0.0617 (2) | 0.0630 (7) | |
H7A | 0.5447 | 0.9118 | −0.0686 | 0.076* | |
C8 | 0.5308 (4) | 0.7499 (2) | −0.0222 (2) | 0.0473 (5) | |
H8A | 0.6738 | 0.7349 | −0.0032 | 0.057* | |
O11 | 0.7241 (2) | 0.14112 (11) | 0.41269 (11) | 0.0408 (3) | |
C11 | 0.8902 (3) | 0.1541 (2) | 0.45469 (14) | 0.0344 (4) | |
C12A | 0.9960 (6) | 0.0581 (3) | 0.5249 (3) | 0.0271 (7) | 0.50 |
H12A | 1.1446 | 0.0710 | 0.5366 | 0.032* | 0.50 |
C12B | 1.0542 (6) | 0.0382 (3) | 0.4654 (3) | 0.0306 (8) | 0.50 |
H12B | 1.1855 | 0.0571 | 0.4942 | 0.037* | 0.50 |
O12 | 0.9558 (2) | 0.24924 (10) | 0.46731 (10) | 0.0362 (3) | |
C13 | 0.8740 (4) | 0.0448 (3) | 0.6234 (2) | 0.0581 (7) | |
C14 | 0.6745 (4) | 0.0199 (2) | 0.6484 (2) | 0.0614 (7) | |
H14A | 0.5990 | −0.0199 | 0.6070 | 0.074* | |
C15 | 0.5850 (5) | 0.0540 (4) | 0.7355 (3) | 0.1023 (15) | |
H15A | 0.4484 | 0.0373 | 0.7533 | 0.123* | |
C16 | 0.6961 (10) | 0.1120 (4) | 0.7953 (2) | 0.120 (2) | |
H16A | 0.6357 | 0.1341 | 0.8544 | 0.144* | |
C17 | 0.8890 (9) | 0.1374 (2) | 0.7708 (2) | 0.0993 (15) | |
H17A | 0.9627 | 0.1783 | 0.8122 | 0.119* | |
C18 | 0.9791 (5) | 0.1043 (3) | 0.6861 (2) | 0.0765 (9) | |
H18A | 1.1156 | 0.1223 | 0.6697 | 0.092* | |
O21 | −0.1697 (3) | 0.6331 (2) | 0.20785 (11) | 0.0480 (4) | |
H211 | −0.277 (4) | 0.605 (2) | 0.2053 (18) | 0.058* | |
H212 | −0.082 (4) | 0.594 (2) | 0.1728 (17) | 0.058* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ca | 0.0227 (2) | 0.0244 (2) | 0.0212 (2) | −0.00323 (13) | −0.00017 (12) | 0.00170 (12) |
O1 | 0.0245 (6) | 0.0241 (6) | 0.0320 (6) | −0.0004 (5) | 0.0016 (5) | 0.0026 (5) |
O2 | 0.0294 (7) | 0.0267 (6) | 0.0340 (7) | −0.0043 (5) | 0.0007 (5) | −0.0011 (5) |
O3 | 0.0502 (8) | 0.0299 (7) | 0.0303 (7) | −0.0098 (6) | −0.0082 (6) | 0.0042 (5) |
O4 | 0.0293 (7) | 0.0373 (7) | 0.0301 (7) | −0.0034 (6) | −0.0042 (5) | −0.0029 (6) |
O5 | 0.0491 (8) | 0.0423 (8) | 0.0301 (7) | 0.0026 (7) | 0.0034 (6) | 0.0021 (6) |
O6 | 0.0486 (9) | 0.0536 (9) | 0.0337 (7) | −0.0257 (7) | −0.0045 (7) | 0.0055 (6) |
O7 | 0.0368 (7) | 0.0444 (7) | 0.0198 (6) | −0.0126 (6) | −0.0005 (5) | 0.0026 (5) |
C1 | 0.0316 (9) | 0.0289 (9) | 0.0230 (8) | −0.0048 (7) | 0.0041 (7) | 0.0002 (7) |
O8 | 0.0354 (7) | 0.0630 (9) | 0.0250 (6) | −0.0179 (6) | 0.0008 (5) | 0.0016 (6) |
C2 | 0.0301 (9) | 0.0423 (10) | 0.0231 (8) | −0.0093 (8) | 0.0017 (7) | −0.0007 (7) |
C3 | 0.0406 (10) | 0.0350 (10) | 0.0276 (9) | −0.0038 (8) | 0.0088 (8) | 0.0003 (7) |
C4 | 0.0418 (11) | 0.0463 (12) | 0.0436 (11) | −0.0062 (9) | 0.0013 (9) | 0.0059 (9) |
C5 | 0.0503 (13) | 0.064 (2) | 0.0550 (14) | 0.0098 (11) | 0.0008 (11) | 0.0172 (12) |
C6 | 0.079 (2) | 0.0422 (13) | 0.075 (2) | 0.0115 (12) | 0.0175 (14) | 0.0238 (12) |
C7 | 0.075 (2) | 0.0389 (12) | 0.076 (2) | −0.0171 (12) | 0.0137 (14) | 0.0101 (11) |
C8 | 0.0455 (12) | 0.0465 (12) | 0.0513 (13) | −0.0123 (10) | 0.0038 (10) | 0.0068 (10) |
O11 | 0.0352 (7) | 0.0252 (6) | 0.0610 (9) | −0.0007 (5) | −0.0093 (6) | −0.0001 (6) |
C11 | 0.0258 (9) | 0.0261 (9) | 0.0496 (11) | 0.0010 (7) | 0.0000 (8) | 0.0102 (8) |
C12A | 0.025 (2) | 0.024 (2) | 0.032 (2) | −0.0028 (14) | 0.000 (2) | −0.002 (2) |
C12B | 0.028 (2) | 0.023 (2) | 0.039 (2) | 0.0003 (15) | −0.003 (2) | 0.001 (2) |
O12 | 0.0315 (7) | 0.0254 (6) | 0.0514 (8) | −0.0028 (5) | −0.0025 (6) | 0.0039 (6) |
C13 | 0.0366 (11) | 0.099 (2) | 0.0322 (11) | 0.0106 (12) | 0.0001 (9) | −0.0128 (11) |
C14 | 0.0472 (13) | 0.0386 (12) | 0.098 (2) | −0.0044 (10) | −0.0095 (13) | −0.0065 (12) |
C15 | 0.065 (2) | 0.112 (3) | 0.117 (3) | 0.017 (2) | 0.049 (2) | 0.067 (3) |
C16 | 0.191 (5) | 0.100 (3) | 0.041 (2) | 0.067 (3) | 0.030 (3) | 0.009 (2) |
C17 | 0.208 (5) | 0.0410 (14) | 0.051 (2) | −0.016 (2) | −0.051 (2) | −0.0006 (13) |
C18 | 0.075 (2) | 0.106 (2) | 0.060 (2) | −0.048 (2) | −0.0282 (14) | 0.039 (2) |
O21 | 0.0359 (8) | 0.0702 (11) | 0.0399 (8) | −0.0140 (7) | −0.0020 (6) | −0.0037 (7) |
Ca—O3 | 2.3799 (13) | C5—C6 | 1.377 (4) |
Ca—O7 | 2.4093 (12) | C6—C7 | 1.367 (4) |
Ca—O6 | 2.4237 (14) | C7—C8 | 1.374 (3) |
Ca—O4 | 2.4728 (13) | O11—C11 | 1.238 (2) |
Ca—O2 | 2.4822 (13) | C11—O12 | 1.252 (2) |
Ca—O5 | 2.5017 (15) | C11—C12A | 1.572 (4) |
Ca—O1i | 2.5264 (13) | C11—C12B | 1.574 (4) |
Ca—O1 | 2.6582 (13) | C12A—C12Aiii | 1.522 (7) |
Ca—Cai | 4.3110 (7) | C12A—C13 | 1.590 (5) |
O1—Cai | 2.5264 (13) | C12B—C12Biii | 1.531 (8) |
O7—C1 | 1.254 (2) | C12B—C13iii | 1.603 (5) |
C1—O8 | 1.247 (2) | C13—C14 | 1.358 (4) |
C1—C2 | 1.540 (2) | C13—C18 | 1.368 (4) |
C2—C2ii | 1.526 (4) | C13—C12Biii | 1.603 (5) |
C2—C3 | 1.528 (3) | C14—C15 | 1.375 (5) |
C3—C8 | 1.379 (3) | C15—C16 | 1.353 (7) |
C3—C4 | 1.390 (3) | C16—C17 | 1.319 (6) |
C4—C5 | 1.384 (3) | C17—C18 | 1.345 (5) |
O3—Ca—O7 | 73.03 (5) | C1—O7—Ca | 136.09 (11) |
O3—Ca—O6 | 138.96 (5) | O8—C1—O7 | 124.8 (2) |
O7—Ca—O6 | 78.01 (5) | O8—C1—C2 | 117.97 (15) |
O3—Ca—O4 | 78.32 (5) | O7—C1—C2 | 117.2 (2) |
O7—Ca—O4 | 92.66 (5) | C2ii—C2—C3 | 111.3 (2) |
O6—Ca—O4 | 74.60 (5) | C2ii—C2—C1 | 110.1 (2) |
O3—Ca—O2 | 142.01 (5) | C3—C2—C1 | 111.14 (14) |
O7—Ca—O2 | 141.86 (4) | C8—C3—C4 | 118.4 (2) |
O6—Ca—O2 | 76.27 (5) | C8—C3—C2 | 118.4 (2) |
O4—Ca—O2 | 106.93 (5) | C4—C3—C2 | 123.1 (2) |
O3—Ca—O5 | 115.20 (5) | C5—C4—C3 | 120.3 (2) |
O7—Ca—O5 | 72.39 (5) | C6—C5—C4 | 120.3 (2) |
O6—Ca—O5 | 81.81 (5) | C7—C6—C5 | 119.4 (2) |
O4—Ca—O5 | 154.35 (5) | C6—C7—C8 | 120.7 (2) |
O2—Ca—O5 | 76.44 (5) | C7—C8—C3 | 120.9 (2) |
O3—Ca—O1i | 72.66 (5) | O11—C11—O12 | 125.3 (2) |
O7—Ca—O1i | 112.62 (4) | O11—C11—C12A | 120.4 (2) |
O6—Ca—O1i | 146.96 (5) | O12—C11—C12A | 111.7 (2) |
O4—Ca—O1i | 132.88 (4) | O11—C11—C12B | 113.5 (2) |
O2—Ca—O1i | 77.50 (4) | O12—C11—C12B | 118.9 (2) |
O5—Ca—O1i | 72.76 (5) | C12Aiii—C12A—C11 | 106.6 (4) |
O3—Ca—O1 | 75.66 (4) | C12Aiii—C12A—C13 | 105.6 (4) |
O7—Ca—O1 | 146.65 (4) | C11—C12A—C13 | 117.8 (3) |
O6—Ca—O1 | 121.18 (5) | C12Biii—C12B—C11 | 106.2 (4) |
O4—Ca—O1 | 69.83 (4) | C12Biii—C12B—C13iii | 104.3 (4) |
O2—Ca—O1 | 71.48 (4) | C11—C12B—C13iii | 121.1 (3) |
O5—Ca—O1 | 133.04 (4) | C14—C13—C18 | 118.5 (2) |
O1i—Ca—O1 | 67.52 (4) | C14—C13—C12A | 133.7 (2) |
O3—Ca—Cai | 70.89 (4) | C18—C13—C12A | 104.6 (2) |
O7—Ca—Cai | 137.77 (3) | C14—C13—C12Biii | 103.7 (2) |
O6—Ca—Cai | 144.14 (4) | C18—C13—C12Biii | 135.4 (3) |
O4—Ca—Cai | 100.73 (3) | C13—C14—C15 | 119.5 (3) |
O2—Ca—Cai | 71.18 (3) | C16—C15—C14 | 119.9 (3) |
O5—Ca—Cai | 104.31 (4) | C17—C16—C15 | 120.8 (3) |
O1i—Ca—Cai | 34.73 (3) | C16—C17—C18 | 120.1 (3) |
O1—Ca—Cai | 32.79 (3) | C17—C18—C13 | 121.3 (3) |
Cai—O1—Ca | 112.48 (4) | ||
O3—Ca—O1—Ca | −76.87 (6) | C6—C7—C8—C3 | −0.5 (4) |
O7—Ca—O1—Ca | −97.38 (8) | C4—C3—C8—C7 | 1.8 (3) |
O6—Ca—O1—Ca | 144.09 (6) | C2—C3—C8—C7 | −179.2 (2) |
O4—Ca—O1—Ca | −159.47 (6) | O11—C11—C12A—C12A | 46.2 (4) |
O2—Ca—O1—Ca | 83.77 (5) | O12—C11—C12A—C12A | −151.4 (3) |
O5—Ca—O1—Ca | 34.38 (8) | C12B—C11—C12A—C12A | −41.5 (3) |
O1—Ca—O1—Ca | 0.0 | O11—C11—C12A—C13 | −72.2 (3) |
Ca—Ca—O1—Ca | 0.0 | O12—C11—C12A—C13 | 90.3 (3) |
O3—Ca—O7—C1 | −143.4 (2) | C12B—C11—C12A—C13 | −159.9 (5) |
O6—Ca—O7—C1 | 7.2 (2) | O11—C11—C12B—C12B | −68.9 (4) |
O4—Ca—O7—C1 | −66.5 (2) | O12—C11—C12B—C12B | 127.6 (3) |
O2—Ca—O7—C1 | 55.6 (2) | C12A—C11—C12B—C12B | 41.1 (3) |
O5—Ca—O7—C1 | 92.3 (2) | O11—C11—C12B—C13 | 49.5 (3) |
O1—Ca—O7—C1 | 154.3 (2) | O12—C11—C12B—C13 | −114.1 (3) |
O1—Ca—O7—C1 | −122.6 (2) | C12A—C11—C12B—C13 | 159.4 (5) |
Ca—Ca—O7—C1 | −175.64 (14) | C12A—C12A—C13—C14 | −59.0 (5) |
Ca—O7—C1—O8 | 18.9 (3) | C11—C12A—C13—C14 | 59.9 (4) |
Ca—O7—C1—C2 | −161.96 (12) | C12A—C12A—C13—C18 | 142.3 (3) |
O8—C1—C2—C2 | −50.4 (3) | C11—C12A—C13—C18 | −98.8 (3) |
O7—C1—C2—C2 | 130.4 (2) | C12A—C12A—C13—C12B | 0.9 (3) |
O8—C1—C2—C3 | 73.3 (2) | C11—C12A—C13—C12B | 119.8 (4) |
O7—C1—C2—C3 | −105.9 (2) | C18—C13—C14—C15 | −0.5 (4) |
C2—C2—C3—C8 | −114.3 (2) | C12A—C13—C14—C15 | −156.8 (3) |
C1—C2—C3—C8 | 122.7 (2) | C12B—C13—C14—C15 | 164.4 (3) |
C2—C2—C3—C4 | 64.7 (3) | C13—C14—C15—C16 | 0.0 (5) |
C1—C2—C3—C4 | −58.3 (2) | C14—C15—C16—C17 | 0.7 (6) |
C8—C3—C4—C5 | −1.8 (3) | C15—C16—C17—C18 | −0.9 (6) |
C2—C3—C4—C5 | 179.2 (2) | C16—C17—C18—C13 | 0.4 (5) |
C3—C4—C5—C6 | 0.6 (4) | C14—C13—C18—C17 | 0.3 (4) |
C4—C5—C6—C7 | 0.8 (4) | C12A—C13—C18—C17 | 162.8 (3) |
C5—C6—C7—C8 | −0.8 (4) | C12B—C13—C18—C17 | −158.6 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z; (iii) −x+2, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H11···O4iv | 0.82 (2) | 2.02 (2) | 2.833 (2) | 177 (2) |
O1—H12···O12i | 0.81 (2) | 1.91 (2) | 2.712 (2) | 173 (2) |
O2—H21···O11 | 0.80 (2) | 1.94 (2) | 2.722 (2) | 165 (2) |
O2—H22···O12v | 0.81 (2) | 1.89 (2) | 2.686 (2) | 166 (2) |
O3—H31···O2i | 0.80 (2) | 1.98 (2) | 2.744 (2) | 158 (2) |
O4—H41···O21 | 0.82 (2) | 1.84 (2) | 2.660 (2) | 175 (2) |
O4—H42···O12i | 0.77 (2) | 2.25 (2) | 2.938 (2) | 150 (2) |
O5—H51···O11 | 0.82 (2) | 2.00 (2) | 2.788 (2) | 162 (2) |
O6—H61···O8 | 0.82 (2) | 1.94 (2) | 2.739 (2) | 165 (2) |
O6—H62···O5v | 0.75 (3) | 2.36 (3) | 3.096 (2) | 166 (2) |
O21—H211···O7v | 0.79 (2) | 2.04 (2) | 2.830 (2) | 178 (2) |
O21—H212···O8 | 0.82 (2) | 2.02 (2) | 2.817 (2) | 167 (2) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (iv) −x, −y+1, −z+1; (v) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | [Ca(C16H12O4)(H2O)6]·H2O |
Mr | 434.45 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 6.2394 (8), 11.6342 (8), 14.1648 (12) |
α, β, γ (°) | 89.697 (7), 88.440 (9), 81.320 (8) |
V (Å3) | 1016.1 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.36 |
Crystal size (mm) | 0.42 × 0.40 × 0.15 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | ψ-scan (North et al., 1968) |
Tmin, Tmax | 0.922, 0.947 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3939, 3580, 3307 |
Rint | 0.010 |
(sin θ/λ)max (Å−1) | 0.594 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.083, 1.06 |
No. of reflections | 3580 |
No. of parameters | 305 |
No. of restraints | 27 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.32, −0.21 |
Computer programs: CAD-4 ARGUS (Enraf-Nonius, 1994), CAD-4 ARGUS, CHI90S (Boyle, 1997), SHELXS86 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXTL (Siemens, 1994).
Ca—O3 | 2.3799 (13) | Ca—O2 | 2.4822 (13) |
Ca—O7 | 2.4093 (12) | Ca—O5 | 2.5017 (15) |
Ca—O6 | 2.4237 (14) | Ca—Cai | 4.3110 (7) |
Ca—O4 | 2.4728 (13) | C2—C3 | 1.528 (3) |
O3—Ca—O7 | 73.03 (5) | O7—Ca—O1 | 146.65 (4) |
O3—Ca—O6 | 138.96 (5) | O6—Ca—O1 | 121.18 (5) |
O7—Ca—O6 | 78.01 (5) | O5—Ca—O1 | 133.04 (4) |
O3—Ca—O4 | 78.32 (5) | O3—Ca—Cai | 70.89 (4) |
O3—Ca—O2 | 142.01 (5) | C1—O7—Ca | 136.09 (11) |
O7—Ca—O2 | 141.86 (4) | C2ii—C2—C3 | 111.3 (2) |
O4—Ca—O2 | 106.93 (5) | C2ii—C2—C1 | 110.1 (2) |
O4—Ca—O5 | 154.35 (5) | ||
O6—Ca—O7—C1 | 7.2 (2) | C1—C2—C3—C4 | −58.3 (2) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H11···O4iii | 0.82 (2) | 2.02 (2) | 2.833 (2) | 177 (2) |
O1—H12···O12i | 0.81 (2) | 1.91 (2) | 2.712 (2) | 173 (2) |
O2—H21···O11 | 0.80 (2) | 1.94 (2) | 2.722 (2) | 165 (2) |
O2—H22···O12iv | 0.81 (2) | 1.89 (2) | 2.686 (2) | 166 (2) |
O3—H31···O2i | 0.80 (2) | 1.98 (2) | 2.744 (2) | 158 (2) |
O4—H41···O21 | 0.82 (2) | 1.84 (2) | 2.660 (2) | 175 (2) |
O4—H42···O12i | 0.77 (2) | 2.25 (2) | 2.938 (2) | 150 (2) |
O5—H51···O11 | 0.82 (2) | 2.00 (2) | 2.788 (2) | 162 (2) |
O6—H61···O8 | 0.82 (2) | 1.94 (2) | 2.739 (2) | 165 (2) |
O6—H62···O5iv | 0.75 (3) | 2.36 (3) | 3.096 (2) | 166 (2) |
O21—H211···O7iv | 0.79 (2) | 2.04 (2) | 2.830 (2) | 178 (2) |
O21—H212···O8 | 0.82 (2) | 2.02 (2) | 2.817 (2) | 167 (2) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z+1; (iv) x−1, y, z. |
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As part of our ongoing study of shape-switchable molecules (Monahan et al., 1998), we have examined some of the structural and environmental factors that control the conformation of meso-2,3-succinate derivatives (-O2CCHXCHXCO2-). In the case of X = OH (meso-tartrate), previous NMR evidence indicates that in aqueous solution the dianion adopts a conformation with the carboxylate groups in a gauche arrangement when the molecule is viewed along the central C2—C3 bond (Ascenso & Gil, 1980). It was of interest to know if other derivatives adopted, or could be forced to adopt, the same unusual conformation. The conformations in alkaline solution were assigned from vicinal H—H coupling constants (3JHH). In the case of X = OCH3, 3JHH = 5.5 Hz, which indicates that a gauche conformation is predominant (Ascenso & Gil, 1980). In the case of X = Br and X = Ph, the 3JHH values of 11.4 and 12.5 Hz, respectively, suggest conformations with the carboxylate groups in an anti orientation. In the case of X = Ph, attempts were made to induce a conformational change to gauche by adding CaCl2 or MgCl2 to the basic aqueous solutions. In both cases, there were only minor changes in 3JHH values (<0.5 Hz) indicating that even in the presence of chelating dications, meso-2,3-diphenylsuccinate remains in an anti conformation. Since this result is counter to that obtained with a related sysytem (Monahan et al., 1998), we decided to confirm our structural assignments with an X-ray analysis of the title crystalline calcium meso-2,3-diphenylsuccinate, (I). \scheme
The crystal structures of a number of succinate salts are known, including the mono- and trihydrates of calcium succinate (Karipides & Reed, 1980; Mathew et al., 1994). However, this is the first reported structure of a 2,3-diphenylsuccinate salt. X-ray analysis of (I) shows that the molecule adopts an anti conformation about the C2—C3 bond (Fig. 1). The crystal consists of layers of a two-dimensional array of succinate dianions that are linked by bridging Ca2+ ions. Along one axis, the carboxylates are directly bonded to the Ca2+ ions, whereas along the other axis they are hydrogen bonded to bridging water molecules. The phenyl rings pack in face-to-face and edge-to-face orientations to form square-shaped nanotubes with aromatic walls, and the interiors of the tubes contain the hydrated calcium carboxylate ion pairs.
The literature structures of calcium succinate show the Ca and the carboxylate O atoms in two types of four-membered rings (Karipides & Reed, 1980; Mathew et al., 1994). Either a carboxylate group forms a bidentate Ca—O—C—O ring, or it provides a bridging unidentate O atom which is part of a four-membered Ca—O—Ca—O ring. As shown in Fig. 1, compound (I) forms a different type of Ca—O—Ca—O ring in which the bridging O atoms belong to water molecules rather than to carboxylates. The internuclear Ca—Ca distance is 4.3110 (7) Å; which is longer than the 3.98–4.01 Å found in the literature succinate Ca—O—Ca—O rings (Karipides & Reed, 1980; Mathew et al., 1994).