Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106037565/fg3031sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270106037565/fg3031Isup2.hkl |
CCDC reference: 628496
2,4-Dichlorophenoxyacetic acid was synthesized according to a literature method (Wu et al., 1996). BaCl2·2H2O (2.40 g, 10 mmol) and 2,4-dichlorophenoxyacetic acid (4.42 g, 20 mmol) were dissolved in a 1:2 ethanol/water mixture and the pH of the solution was adjusted to 7 with 0.1 M sodium hydroxide. The reaction mixture was stirred for 30 min at room temperature and then filtered. Colorless crystals were formed in a few days in the solution left at room temperature. Analysis calculated for C16H14BaCl4O8: C 31.33, H 2.30%; found: C 31.29, H 2.31%.
H atoms attached to C atoms were placed in calculated positions and treated as riding, with C—H distances of 0.93 and 0.97 Å and Uiso(H) values of 1.2Ueq(C). H atoms of water molecule were located in a difference Fourier map and refined with an O—H distance restraint of 0.85 (1) Å, and Uiso(H) value of 1.5Ueq(O).
Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
[Ba(C8H5Cl2O3)2(H2O)]·H2O | F(000) = 1192 |
Mr = 613.41 | Dx = 2.024 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 14172 reflections |
a = 18.671 (4) Å | θ = 3.0–25.0° |
b = 7.7027 (15) Å | µ = 2.55 mm−1 |
c = 14.002 (3) Å | T = 295 K |
β = 90.99 (3)° | Prism, colorless |
V = 2013.4 (7) Å3 | 0.36 × 0.25 × 0.18 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | 3541 independent reflections |
Radiation source: fine-focus sealed tube | 3185 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.087 |
Detector resolution: 10 pixels mm-1 | θmax = 25.0°, θmin = 3.0° |
ω scans | h = −22→22 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −9→8 |
Tmin = 0.471, Tmax = 0.637 | l = −16→16 |
14924 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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0081P)2 + 16.8794P] where P = (Fo2 + 2Fc2)/3 |
3541 reflections | (Δ/σ)max = 0.001 |
274 parameters | Δρmax = 2.32 e Å−3 |
6 restraints | Δρmin = −1.50 e Å−3 |
[Ba(C8H5Cl2O3)2(H2O)]·H2O | V = 2013.4 (7) Å3 |
Mr = 613.41 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 18.671 (4) Å | µ = 2.55 mm−1 |
b = 7.7027 (15) Å | T = 295 K |
c = 14.002 (3) Å | 0.36 × 0.25 × 0.18 mm |
β = 90.99 (3)° |
Rigaku R-AXIS RAPID diffractometer | 3541 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 3185 reflections with I > 2σ(I) |
Tmin = 0.471, Tmax = 0.637 | Rint = 0.087 |
14924 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 6 restraints |
wR(F2) = 0.123 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0081P)2 + 16.8794P] where P = (Fo2 + 2Fc2)/3 |
3541 reflections | Δρmax = 2.32 e Å−3 |
274 parameters | Δρmin = −1.50 e Å−3 |
x | y | z | Uiso*/Ueq | ||
Ba1 | 0.02667 (2) | 0.73040 (5) | 0.68705 (3) | 0.02252 (16) | |
Cl1 | 0.21027 (10) | 0.7739 (2) | 0.75017 (13) | 0.0371 (4) | |
Cl2 | 0.43640 (11) | 0.6487 (3) | 0.52774 (18) | 0.0577 (6) | |
Cl3 | 0.33276 (12) | 0.2678 (3) | 0.47834 (14) | 0.0473 (5) | |
Cl4 | 0.53371 (12) | −0.0288 (4) | 0.70151 (19) | 0.0648 (7) | |
O1W | 0.1776 (3) | 0.4641 (8) | 0.4433 (4) | 0.0464 (14) | |
O2W | −0.0546 (3) | 0.4275 (7) | 0.6431 (3) | 0.0335 (11) | |
O1 | 0.0355 (2) | 1.0906 (6) | 0.6440 (3) | 0.0279 (10) | |
O2 | 0.0144 (3) | 1.2253 (6) | 0.5039 (3) | 0.0290 (10) | |
O3 | 0.1450 (3) | 0.9176 (6) | 0.5804 (3) | 0.0311 (11) | |
O4 | 0.1287 (3) | 0.4743 (6) | 0.6235 (3) | 0.0350 (11) | |
O5 | 0.0918 (2) | 0.4185 (6) | 0.7698 (3) | 0.0303 (11) | |
O6 | 0.2456 (3) | 0.2688 (7) | 0.6474 (4) | 0.0351 (12) | |
C1 | 0.0498 (3) | 1.1258 (8) | 0.5590 (4) | 0.0235 (13) | |
C2 | 0.1148 (4) | 1.0435 (8) | 0.5149 (4) | 0.0264 (14) | |
C3 | 0.2122 (4) | 0.8572 (8) | 0.5628 (5) | 0.0268 (14) | |
C4 | 0.2497 (4) | 0.7800 (8) | 0.6393 (5) | 0.0274 (14) | |
C5 | 0.3168 (4) | 0.7121 (9) | 0.6278 (6) | 0.0382 (18) | |
C6 | 0.3497 (4) | 0.7239 (10) | 0.5415 (6) | 0.0388 (18) | |
C7 | 0.3146 (4) | 0.8028 (10) | 0.4647 (6) | 0.0409 (18) | |
C8 | 0.2462 (4) | 0.8679 (9) | 0.4761 (5) | 0.0329 (16) | |
C9 | 0.1351 (3) | 0.4004 (8) | 0.7015 (5) | 0.0255 (14) | |
C10 | 0.1985 (4) | 0.2840 (9) | 0.7263 (5) | 0.0326 (16) | |
C11 | 0.3106 (4) | 0.1936 (9) | 0.6653 (5) | 0.0307 (15) | |
C12 | 0.3586 (4) | 0.1880 (9) | 0.5893 (5) | 0.0306 (15) | |
C13 | 0.4264 (4) | 0.1197 (10) | 0.6003 (5) | 0.0370 (17) | |
C14 | 0.4465 (4) | 0.0540 (10) | 0.6889 (6) | 0.0384 (18) | |
C15 | 0.4014 (4) | 0.0525 (10) | 0.7619 (6) | 0.0399 (18) | |
C16 | 0.3330 (4) | 0.1210 (9) | 0.7511 (5) | 0.0334 (16) | |
H1W1 | 0.159 (4) | 0.458 (13) | 0.498 (3) | 0.070* | |
H1W2 | 0.2219 (14) | 0.488 (13) | 0.449 (5) | 0.070* | |
H2W1 | −0.0974 (15) | 0.449 (11) | 0.625 (5) | 0.050* | |
H2W2 | −0.031 (3) | 0.387 (11) | 0.597 (3) | 0.050* | |
H2A | 0.1013 | 0.9871 | 0.4553 | 0.032* | |
H2B | 0.1502 | 1.1320 | 0.5012 | 0.032* | |
H5 | 0.3401 | 0.6578 | 0.6788 | 0.046* | |
H7 | 0.3370 | 0.8119 | 0.4061 | 0.049* | |
H8 | 0.2226 | 0.9197 | 0.4244 | 0.039* | |
H10A | 0.2245 | 0.3319 | 0.7808 | 0.039* | |
H10B | 0.1813 | 0.1697 | 0.7438 | 0.039* | |
H13 | 0.4579 | 0.1177 | 0.5495 | 0.044* | |
H15 | 0.4160 | 0.0053 | 0.8202 | 0.048* | |
H16 | 0.3019 | 0.1180 | 0.8022 | 0.040* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ba1 | 0.0292 (2) | 0.0202 (2) | 0.0182 (2) | 0.00118 (15) | 0.00247 (15) | 0.00091 (14) |
Cl1 | 0.0395 (10) | 0.0477 (10) | 0.0241 (9) | −0.0017 (8) | 0.0003 (7) | 0.0047 (7) |
Cl2 | 0.0320 (11) | 0.0657 (14) | 0.0756 (16) | 0.0111 (10) | 0.0080 (10) | 0.0084 (12) |
Cl3 | 0.0512 (12) | 0.0567 (12) | 0.0340 (10) | 0.0085 (10) | 0.0057 (9) | 0.0122 (9) |
Cl4 | 0.0375 (12) | 0.0778 (17) | 0.0786 (17) | 0.0213 (11) | −0.0072 (11) | 0.0019 (13) |
O1W | 0.043 (3) | 0.065 (4) | 0.031 (3) | 0.005 (3) | −0.003 (2) | 0.000 (3) |
O2W | 0.038 (3) | 0.037 (3) | 0.026 (2) | 0.006 (2) | −0.003 (2) | −0.001 (2) |
O1 | 0.037 (3) | 0.026 (2) | 0.021 (2) | 0.000 (2) | 0.007 (2) | 0.0038 (19) |
O2 | 0.037 (3) | 0.029 (2) | 0.021 (2) | 0.003 (2) | −0.003 (2) | 0.0038 (19) |
O3 | 0.031 (3) | 0.036 (3) | 0.026 (2) | 0.008 (2) | 0.004 (2) | 0.006 (2) |
O4 | 0.039 (3) | 0.036 (3) | 0.030 (3) | 0.007 (2) | 0.006 (2) | 0.004 (2) |
O5 | 0.030 (3) | 0.029 (2) | 0.032 (3) | 0.000 (2) | 0.007 (2) | 0.000 (2) |
O6 | 0.029 (3) | 0.049 (3) | 0.028 (3) | 0.010 (2) | 0.003 (2) | −0.001 (2) |
C1 | 0.028 (3) | 0.021 (3) | 0.021 (3) | −0.004 (3) | −0.002 (3) | −0.003 (3) |
C2 | 0.033 (4) | 0.026 (3) | 0.021 (3) | −0.003 (3) | 0.003 (3) | 0.006 (3) |
C3 | 0.026 (3) | 0.027 (3) | 0.028 (3) | 0.000 (3) | −0.004 (3) | −0.001 (3) |
C4 | 0.031 (4) | 0.025 (3) | 0.025 (3) | −0.002 (3) | 0.000 (3) | 0.000 (3) |
C5 | 0.030 (4) | 0.034 (4) | 0.050 (5) | 0.002 (3) | −0.005 (3) | 0.005 (3) |
C6 | 0.029 (4) | 0.036 (4) | 0.051 (5) | 0.003 (3) | 0.005 (3) | −0.012 (4) |
C7 | 0.040 (4) | 0.048 (5) | 0.035 (4) | 0.000 (4) | 0.012 (3) | −0.004 (4) |
C8 | 0.042 (4) | 0.037 (4) | 0.020 (3) | 0.000 (3) | 0.003 (3) | 0.000 (3) |
C9 | 0.026 (3) | 0.024 (3) | 0.027 (3) | −0.005 (3) | 0.003 (3) | −0.007 (3) |
C10 | 0.036 (4) | 0.035 (4) | 0.027 (4) | 0.005 (3) | 0.004 (3) | −0.001 (3) |
C11 | 0.031 (4) | 0.032 (4) | 0.030 (4) | −0.002 (3) | 0.001 (3) | 0.000 (3) |
C12 | 0.034 (4) | 0.030 (3) | 0.027 (3) | 0.002 (3) | 0.002 (3) | 0.002 (3) |
C13 | 0.029 (4) | 0.046 (4) | 0.036 (4) | 0.003 (3) | 0.007 (3) | −0.001 (3) |
C14 | 0.029 (4) | 0.036 (4) | 0.050 (5) | 0.005 (3) | −0.004 (3) | −0.010 (4) |
C15 | 0.038 (4) | 0.043 (4) | 0.038 (4) | 0.008 (3) | −0.013 (3) | −0.003 (3) |
C16 | 0.032 (4) | 0.038 (4) | 0.029 (4) | 0.002 (3) | −0.001 (3) | −0.001 (3) |
Ba1—O1 | 2.844 (4) | O5—Ba1i | 2.720 (5) |
Ba1—O1i | 2.863 (4) | O5—C9 | 1.270 (8) |
Ba1—O2ii | 2.790 (5) | O6—C11 | 1.364 (9) |
Ba1—O3 | 3.050 (5) | O6—C10 | 1.429 (8) |
Ba1—O4 | 2.894 (5) | C1—C2 | 1.512 (9) |
Ba1—O5 | 2.922 (5) | C2—H2A | 0.9700 |
Ba1—O5iii | 2.720 (5) | C2—H2B | 0.9700 |
Ba1—O2W | 2.845 (5) | C3—C4 | 1.402 (9) |
Ba1—O2Wiii | 2.861 (5) | C3—C8 | 1.381 (9) |
Cl1—C4 | 1.730 (7) | C4—C5 | 1.370 (10) |
Cl2—C6 | 1.734 (8) | C5—C6 | 1.368 (11) |
O1—C1 | 1.255 (7) | C5—H5 | 0.9300 |
O2—C1 | 1.264 (8) | C6—C7 | 1.389 (12) |
Ba1—Ba1iii | 4.3581 (8) | C7—C8 | 1.384 (10) |
Ba1—Cl1 | 3.541 (2) | C7—H7 | 0.9300 |
Ba1—C9 | 3.254 (7) | C8—H8 | 0.9300 |
Cl3—C12 | 1.732 (7) | C9—C10 | 1.521 (9) |
Cl4—C14 | 1.755 (7) | C10—H10A | 0.9700 |
O1W—H1W1 | 0.85 (5) | C10—H10B | 0.9700 |
O1W—H1W2 | 0.85 (4) | C11—C16 | 1.384 (10) |
O2W—Ba1i | 2.861 (5) | C11—C12 | 1.403 (10) |
O2W—H2W1 | 0.85 (4) | C12—C13 | 1.377 (10) |
O2W—H2W2 | 0.85 (5) | C13—C14 | 1.385 (11) |
O1—Ba1iii | 2.863 (4) | C13—H13 | 0.9300 |
O2—Ba1ii | 2.790 (5) | C14—C15 | 1.336 (11) |
O3—C2 | 1.442 (8) | C15—C16 | 1.387 (10) |
O3—C3 | 1.366 (8) | C15—H15 | 0.9300 |
O4—C9 | 1.236 (8) | C16—H16 | 0.9300 |
O1—Ba1—O1i | 124.59 (11) | O5—Ba1—Ba1iii | 131.49 (9) |
O1—Ba1—O3 | 52.42 (12) | O5iii—Ba1—Ba1iii | 41.15 (10) |
O1i—Ba1—O3 | 152.85 (13) | O5—Ba1—Cl1 | 65.46 (10) |
O1—Ba1—O4 | 123.98 (13) | O5iii—Ba1—Cl1 | 132.93 (11) |
O1i—Ba1—O4 | 106.04 (13) | O5iii—Ba1—C9 | 155.44 (15) |
O1—Ba1—O5 | 149.37 (14) | O5—Ba1—C9 | 22.94 (14) |
O1i—Ba1—O5 | 62.29 (12) | O5—C9—Ba1 | 63.7 (3) |
O1—Ba1—O2W | 141.88 (14) | O5—C9—C10 | 113.4 (6) |
O1—Ba1—O2Wiii | 69.39 (13) | O6—C11—C12 | 116.8 (6) |
O2ii—Ba1—O1i | 136.83 (14) | O6—C11—C16 | 125.9 (6) |
O2ii—Ba1—O1 | 72.16 (13) | O6—C10—C9 | 111.1 (6) |
O2ii—Ba1—O3 | 70.24 (13) | O6—C10—H10A | 109.4 |
O2ii—Ba1—O4 | 87.71 (14) | O6—C10—H10B | 109.4 |
O2ii—Ba1—O5 | 125.88 (13) | O2W—Ba1—Ba1iii | 133.42 (10) |
O2ii—Ba1—O2W | 75.91 (13) | O2Wiii—Ba1—Ba1iii | 40.06 (10) |
O2ii—Ba1—O2Wiii | 140.77 (14) | O2W—Ba1—Cl1 | 129.95 (11) |
O4—Ba1—O3 | 71.66 (13) | O2Wiii—Ba1—Cl1 | 65.20 (11) |
O4—Ba1—O5 | 44.78 (13) | O2W—Ba1—C9 | 72.65 (15) |
O5iii—Ba1—O1 | 65.02 (13) | O2Wiii—Ba1—C9 | 104.98 (15) |
O5iii—Ba1—O1i | 70.99 (13) | C1—O1—Ba1 | 115.2 (4) |
O5iii—Ba1—O2ii | 86.38 (14) | C1—O1—Ba1iii | 143.0 (4) |
O5iii—Ba1—O3 | 117.08 (13) | C1—O2—Ba1ii | 142.2 (4) |
O5—Ba1—O3 | 106.45 (12) | C1—C2—H2A | 109.8 |
O5iii—Ba1—O4 | 166.80 (15) | C1—C2—H2B | 109.8 |
O5iii—Ba1—O5 | 133.14 (8) | C2—O3—Ba1 | 110.6 (4) |
O5iii—Ba1—O2W | 92.99 (14) | C3—O3—Ba1 | 127.1 (4) |
O5iii—Ba1—O2Wiii | 70.73 (15) | C3—O3—C2 | 117.6 (5) |
O2W—Ba1—O1i | 69.36 (13) | C3—C4—Cl1 | 118.9 (5) |
O2Wiii—Ba1—O1i | 65.41 (13) | C3—C8—C7 | 121.2 (7) |
O2W—Ba1—O3 | 132.07 (13) | C3—C8—H8 | 119.4 |
O2Wiii—Ba1—O3 | 91.88 (14) | C4—Cl1—Ba1 | 101.7 (2) |
O2W—Ba1—O4 | 74.11 (15) | C4—C5—H5 | 119.9 |
O2Wiii—Ba1—O4 | 120.38 (15) | C5—C4—Cl1 | 120.0 (6) |
O2W—Ba1—O5 | 68.18 (14) | C5—C4—C3 | 121.1 (7) |
O2Wiii—Ba1—O5 | 92.19 (14) | C5—C6—Cl2 | 120.7 (7) |
O2W—Ba1—O2Wiii | 134.73 (9) | C5—C6—C7 | 120.0 (7) |
Ba1—O1—Ba1iii | 99.57 (13) | C6—C5—C4 | 120.3 (7) |
Ba1i—O5—Ba1 | 101.07 (15) | C6—C5—H5 | 119.9 |
Ba1—O2W—Ba1i | 99.59 (15) | C6—C7—H7 | 120.2 |
Ba1—O2W—H2W1 | 114 (6) | C7—C6—Cl2 | 119.3 (6) |
Ba1i—O2W—H2W1 | 121 (5) | C7—C8—H8 | 119.4 |
Ba1—O2W—H2W2 | 101 (6) | C8—C3—C4 | 117.8 (6) |
Ba1i—O2W—H2W2 | 111 (5) | C8—C7—C6 | 119.5 (7) |
Cl1—Ba1—Ba1iii | 92.43 (3) | C8—C7—H7 | 120.2 |
C11—O6—C10 | 116.8 (5) | C9—Ba1—Ba1iii | 144.25 (11) |
O1i—Ba1—Ba1iii | 84.23 (9) | C9—Ba1—Cl1 | 57.31 (12) |
O1—Ba1—Ba1iii | 40.37 (9) | C9—O4—Ba1 | 95.5 (4) |
O1—Ba1—Cl1 | 84.33 (10) | C9—O5—Ba1i | 129.7 (4) |
O1i—Ba1—Cl1 | 103.53 (10) | C9—O5—Ba1 | 93.3 (4) |
O1—Ba1—C9 | 137.48 (15) | C9—C10—H10A | 109.4 |
O1i—Ba1—C9 | 85.14 (15) | C9—C10—H10B | 109.4 |
O1—C1—O2 | 126.3 (6) | C10—C9—Ba1 | 163.0 (4) |
O1—C1—C2 | 118.8 (6) | C11—C12—Cl3 | 119.9 (5) |
O2ii—Ba1—Ba1iii | 102.63 (9) | C11—C16—C15 | 120.8 (7) |
O2ii—Ba1—Cl1 | 118.45 (11) | C11—C16—H16 | 119.6 |
O2ii—Ba1—C9 | 108.40 (15) | C12—C13—C14 | 118.3 (7) |
O2—C1—C2 | 114.9 (5) | C12—C13—H13 | 120.9 |
O3—Ba1—Ba1iii | 87.29 (9) | C13—C12—C11 | 121.6 (7) |
O3—Ba1—Cl1 | 51.06 (9) | C13—C12—Cl3 | 118.5 (5) |
O3—Ba1—C9 | 86.85 (14) | C13—C14—Cl4 | 117.4 (6) |
O3—C2—C1 | 109.2 (5) | C14—C13—H13 | 120.9 |
O3—C2—H2A | 109.8 | C14—C15—C16 | 120.3 (7) |
O3—C2—H2B | 109.8 | C14—C15—H15 | 119.8 |
O3—C3—C4 | 117.0 (6) | C15—C14—C13 | 121.6 (7) |
O3—C3—C8 | 125.1 (6) | C15—C14—Cl4 | 121.0 (6) |
O4—Ba1—Ba1iii | 152.03 (10) | C15—C16—H16 | 119.6 |
O4—Ba1—Cl1 | 60.10 (11) | C16—C11—C12 | 117.3 (7) |
O4—Ba1—C9 | 22.23 (14) | C16—C15—H15 | 119.8 |
O4—C9—Ba1 | 62.3 (3) | H2A—C2—H2B | 108.3 |
O4—C9—O5 | 124.2 (6) | H10A—C10—H10B | 108.0 |
O4—C9—C10 | 122.4 (6) | ||
Ba1iii—Ba1—Cl1—C4 | −116.3 (2) | O3—C3—C8—C7 | −179.9 (7) |
Ba1iii—Ba1—O2W—Ba1i | −94.65 (15) | O4—Ba1—Cl1—C4 | 58.1 (2) |
Ba1iii—Ba1—O1—C1 | −167.1 (5) | O4—Ba1—O2W—Ba1i | 79.54 (15) |
Ba1iii—Ba1—O3—C2 | −64.0 (4) | O4—Ba1—O1—Ba1iii | −148.38 (14) |
Ba1iii—Ba1—O3—C3 | 141.1 (5) | O4—Ba1—O1—C1 | 44.5 (5) |
Ba1iii—Ba1—O4—C9 | 88.1 (4) | O4—Ba1—O3—C2 | 134.7 (4) |
Ba1iii—Ba1—O5—Ba1i | 94.79 (14) | O4—Ba1—O3—C3 | −20.2 (5) |
Ba1iii—Ba1—O5—C9 | −133.6 (3) | O4—Ba1—O5—Ba1i | −123.7 (2) |
Ba1iii—Ba1—C9—O4 | −126.6 (4) | O4—Ba1—O5—C9 | 7.9 (3) |
Ba1iii—Ba1—C9—O5 | 68.1 (4) | O4—Ba1—C9—O5 | −165.2 (6) |
Ba1iii—Ba1—C9—C10 | −16.2 (16) | O4—Ba1—C9—C10 | 110.5 (16) |
Ba1—Cl1—C4—C5 | −147.6 (5) | O4—C9—C10—O6 | −2.3 (9) |
Ba1—Cl1—C4—C3 | 33.2 (6) | O5iii—Ba1—Cl1—C4 | −124.5 (3) |
Ba1—O1—C1—O2 | 126.7 (6) | O5—Ba1—Cl1—C4 | 108.5 (2) |
Ba1iii—O1—C1—O2 | −31.8 (11) | O5iii—Ba1—O2W—Ba1i | −103.31 (16) |
Ba1—O1—C1—C2 | −52.8 (7) | O5—Ba1—O2W—Ba1i | 32.47 (13) |
Ba1iii—O1—C1—C2 | 148.6 (5) | O5—Ba1—O1—Ba1iii | −91.2 (2) |
Ba1ii—O2—C1—O1 | −145.9 (5) | O5iii—Ba1—O1—Ba1iii | 42.74 (14) |
Ba1ii—O2—C1—C2 | 33.7 (9) | O5iii—Ba1—O1—C1 | −124.3 (5) |
Ba1—O3—C2—C1 | 36.4 (6) | O5—Ba1—O1—C1 | 101.7 (5) |
Ba1—O3—C3—C4 | −46.0 (8) | O5iii—Ba1—O3—C3 | 170.5 (5) |
Ba1—O3—C3—C8 | 134.6 (6) | O5iii—Ba1—O3—C2 | −34.6 (4) |
Ba1—O4—C9—O5 | 16.0 (7) | O5—Ba1—O3—C2 | 163.3 (4) |
Ba1—O4—C9—C10 | −161.0 (5) | O5—Ba1—O3—C3 | 8.4 (5) |
Ba1i—O5—C9—Ba1 | 107.4 (4) | O5iii—Ba1—O4—C9 | −95.5 (7) |
Ba1i—O5—C9—O4 | 91.5 (7) | O5—Ba1—O4—C9 | −8.1 (4) |
Ba1—O5—C9—O4 | −15.8 (7) | O5iii—Ba1—O5—Ba1i | 38.08 (19) |
Ba1i—O5—C9—C10 | −91.2 (6) | O5iii—Ba1—O5—C9 | 169.6 (4) |
Ba1—O5—C9—C10 | 161.5 (5) | O5iii—Ba1—C9—O4 | 146.9 (4) |
Ba1—C9—C10—O6 | −103.2 (15) | O5—Ba1—C9—O4 | 165.2 (6) |
Cl1—Ba1—O2W—Ba1i | 55.68 (18) | O5iii—Ba1—C9—O5 | −18.4 (7) |
Cl1—Ba1—O1—Ba1iii | −100.52 (12) | O5iii—Ba1—C9—C10 | −102.7 (15) |
Cl1—Ba1—O1—C1 | 92.4 (4) | O5—Ba1—C9—C10 | −84.3 (15) |
Cl1—Ba1—O3—C2 | −159.3 (4) | O5—C9—C10—O6 | −179.7 (5) |
Cl1—Ba1—O3—C3 | 45.7 (4) | O6—C11—C12—C13 | 178.1 (7) |
Cl1—Ba1—O4—C9 | 76.1 (4) | O6—C11—C12—Cl3 | −2.1 (9) |
Cl1—Ba1—O5—C9 | −63.6 (4) | O6—C11—C16—C15 | −178.1 (7) |
Cl1—Ba1—O5—Ba1i | 164.83 (16) | O2W—Ba1—Cl1—C4 | 84.8 (3) |
Cl1—Ba1—C9—O4 | −90.3 (4) | O2Wiii—Ba1—Cl1—C4 | −146.6 (3) |
Cl1—Ba1—C9—O5 | 104.5 (4) | O2Wiii—Ba1—O2W—Ba1i | −37.7 (2) |
Cl1—Ba1—C9—C10 | 20.2 (15) | O2W—Ba1—O1—Ba1iii | 102.7 (2) |
C11—O6—C10—C9 | 168.8 (6) | O2Wiii—Ba1—O1—Ba1iii | −34.92 (14) |
Cl1—C4—C5—C6 | −176.9 (6) | O2W—Ba1—O1—C1 | −64.4 (5) |
Cl2—C6—C7—C8 | −178.0 (6) | O2Wiii—Ba1—O1—C1 | 158.0 (5) |
O1—Ba1—Cl1—C4 | −76.7 (2) | O2W—Ba1—O3—C2 | 88.1 (4) |
O1i—Ba1—Cl1—C4 | 159.0 (2) | O2Wiii—Ba1—O3—C2 | −103.8 (4) |
O1—Ba1—O2W—Ba1i | −155.10 (15) | O2W—Ba1—O3—C3 | −66.8 (5) |
O1i—Ba1—O2W—Ba1i | −34.92 (13) | O2Wiii—Ba1—O3—C3 | 101.3 (5) |
O1i—Ba1—O1—C1 | −165.1 (5) | O2W—Ba1—O4—C9 | −82.9 (4) |
O1—Ba1—O3—C2 | −41.8 (4) | O2Wiii—Ba1—O4—C9 | 50.0 (4) |
O1i—Ba1—O3—C2 | −135.8 (4) | O2W—Ba1—O5—Ba1i | −34.57 (14) |
O1—Ba1—O3—C3 | 163.3 (5) | O2Wiii—Ba1—O5—Ba1i | 103.45 (16) |
O1i—Ba1—O3—C3 | 69.3 (6) | O2W—Ba1—O5—C9 | 97.0 (4) |
O1—Ba1—O4—C9 | 134.5 (4) | O2Wiii—Ba1—O5—C9 | −125.0 (4) |
O1i—Ba1—O4—C9 | −20.5 (4) | O2W—Ba1—C9—O4 | 90.4 (4) |
O1—Ba1—O5—C9 | −73.8 (4) | O2Wiii—Ba1—C9—O4 | −136.8 (4) |
O1—Ba1—O5—Ba1i | 154.62 (18) | O2W—Ba1—C9—O5 | −74.9 (4) |
O1i—Ba1—O5—Ba1i | 42.81 (13) | O2Wiii—Ba1—C9—O5 | 57.9 (4) |
O1i—Ba1—O5—C9 | 174.4 (4) | O2W—Ba1—C9—C10 | −159.1 (15) |
O1—Ba1—C9—O4 | −61.1 (5) | O2Wiii—Ba1—C9—C10 | −26.3 (15) |
O1i—Ba1—C9—O4 | 160.3 (4) | C2—O3—C3—C4 | 160.6 (6) |
O1—Ba1—C9—O5 | 133.6 (3) | C2—O3—C3—C8 | −18.7 (9) |
O1i—Ba1—C9—O5 | −5.0 (4) | C3—O3—C2—C1 | −166.0 (5) |
O1—Ba1—C9—C10 | 49.3 (16) | C3—C4—C5—C6 | 2.3 (11) |
O1i—Ba1—C9—C10 | −89.3 (15) | C4—C3—C8—C7 | 0.7 (10) |
O1—C1—C2—O3 | 6.8 (8) | C4—C5—C6—Cl2 | 176.6 (6) |
O2ii—Ba1—Cl1—C4 | −10.6 (3) | C4—C5—C6—C7 | −0.9 (12) |
O2ii—Ba1—O2W—Ba1i | 171.18 (17) | C5—C6—C7—C8 | −0.5 (12) |
O2ii—Ba1—O1—Ba1iii | 137.15 (17) | C6—C7—C8—C3 | 0.6 (12) |
O2ii—Ba1—O1—C1 | −29.9 (4) | C8—C3—C4—Cl1 | 177.0 (5) |
O2ii—Ba1—O3—C2 | 40.4 (4) | C8—C3—C4—C5 | −2.1 (10) |
O2ii—Ba1—O3—C3 | −114.5 (5) | C9—Ba1—Cl1—C4 | 84.0 (3) |
O2ii—Ba1—O4—C9 | −158.9 (4) | C9—Ba1—O2W—Ba1i | 56.38 (16) |
O2ii—Ba1—O5—Ba1i | −86.74 (18) | C9—Ba1—O1—Ba1iii | −124.83 (19) |
O2ii—Ba1—O5—C9 | 44.8 (4) | C9—Ba1—O1—C1 | 68.1 (5) |
O2ii—Ba1—C9—O4 | 22.3 (4) | C9—Ba1—O3—C2 | 151.3 (4) |
O2ii—Ba1—C9—O5 | −143.0 (4) | C9—Ba1—O3—C3 | −3.6 (5) |
O2ii—Ba1—C9—C10 | 132.7 (15) | C9—Ba1—O5—Ba1i | −131.6 (4) |
O2—C1—C2—O3 | −172.9 (5) | C10—O6—C11—C12 | −176.3 (6) |
O3—Ba1—Cl1—C4 | −31.8 (2) | C10—O6—C11—C16 | 4.5 (10) |
O3—Ba1—O2W—Ba1i | 125.30 (15) | C11—C12—C13—C14 | 0.6 (11) |
O3—Ba1—O1—Ba1iii | −144.4 (2) | C12—C13—C14—Cl4 | −178.9 (6) |
O3—Ba1—O1—C1 | 48.5 (4) | C12—C13—C14—C15 | 1.5 (12) |
O3—Ba1—O4—C9 | 131.2 (4) | C12—C11—C16—C15 | 2.7 (11) |
O3—Ba1—O5—Ba1i | −163.94 (13) | Cl3—C12—C13—C14 | −179.2 (6) |
O3—Ba1—O5—C9 | −32.4 (4) | C13—C14—C15—C16 | −1.4 (12) |
O3—Ba1—C9—O4 | −45.7 (4) | Cl4—C14—C15—C16 | 179.0 (6) |
O3—Ba1—C9—O5 | 149.0 (4) | C14—C15—C16—C11 | −0.8 (12) |
O3—Ba1—C9—C10 | 64.8 (15) | C16—C11—C12—C13 | −2.7 (11) |
O3—C3—C4—Cl1 | −2.4 (8) | C16—C11—C12—Cl3 | 177.2 (6) |
O3—C3—C4—C5 | 178.4 (6) |
Symmetry codes: (i) −x, y−1/2, −z+3/2; (ii) −x, −y+2, −z+1; (iii) −x, y+1/2, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O4 | 0.85 (5) | 1.86 (6) | 2.699 (7) | 170 (4) |
O1W—H1W2···Cl3 | 0.85 (4) | 2.70 (8) | 3.296 (6) | 128 (8) |
O2W—H2W1···O1Wiv | 0.85 (4) | 1.89 (3) | 2.709 (7) | 163 (8) |
O2W—H2W2···O2v | 0.85 (5) | 2.00 (7) | 2.824 (7) | 163 (8) |
Symmetry codes: (iv) −x, −y+1, −z+1; (v) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | [Ba(C8H5Cl2O3)2(H2O)]·H2O |
Mr | 613.41 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 295 |
a, b, c (Å) | 18.671 (4), 7.7027 (15), 14.002 (3) |
β (°) | 90.99 (3) |
V (Å3) | 2013.4 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.55 |
Crystal size (mm) | 0.36 × 0.25 × 0.18 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.471, 0.637 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14924, 3541, 3185 |
Rint | 0.087 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.123, 1.08 |
No. of reflections | 3541 |
No. of parameters | 274 |
No. of restraints | 6 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
w = 1/[σ2(Fo2) + (0.0081P)2 + 16.8794P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 2.32, −1.50 |
Computer programs: RAPID-AUTO (Rigaku Corporation, 1998), RAPID-AUTO, CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97.
Ba1—O1 | 2.844 (4) | Ba1—O5 | 2.922 (5) |
Ba1—O1i | 2.863 (4) | Ba1—O5iii | 2.720 (5) |
Ba1—O2ii | 2.790 (5) | Ba1—O2W | 2.845 (5) |
Ba1—O3 | 3.050 (5) | Ba1—O2Wiii | 2.861 (5) |
Ba1—O4 | 2.894 (5) |
Symmetry codes: (i) −x, y−1/2, −z+3/2; (ii) −x, −y+2, −z+1; (iii) −x, y+1/2, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O4 | 0.85 (5) | 1.86 (6) | 2.699 (7) | 170 (4) |
O1W—H1W2···Cl3 | 0.85 (4) | 2.70 (8) | 3.296 (6) | 128 (8) |
O2W—H2W1···O1Wiv | 0.85 (4) | 1.89 (3) | 2.709 (7) | 163 (8) |
O2W—H2W2···O2v | 0.85 (5) | 2.00 (7) | 2.824 (7) | 163 (8) |
Symmetry codes: (iv) −x, −y+1, −z+1; (v) x, y−1, z. |
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The formation of metal-organic coordination polymers has received much attention in recent years (Plater et al., 1998). In this context, it is surprising to see the relatively small number of group II coordination polymers in the literature (Platers et al., 1997). In addition, the coordination number is not limited to six for the larger group II metals, where a higher coordination number may be expected. 2,4-Dichlorophenoxyacetic acid, which has been commonly used in herbicides and plant growth substances (Lv, 1998), has versatile bonding modes with metal ions (Liang et al., 2002) and, because of its versatile coordination modes, 2,4-dichlorophenoxyacetic acid may take part in hydrogen-bonding interactions by functioning as either a hydrogen-bond donor or an acceptor. We report here a novel two-dimensional coordination polymer, {[Ba(C8H5Cl2O3)2(H2O)]·H2O}n, (I), based on the group II metal BaII atom with the 2,4-dichlorophenoxyacetate dianion. Owing to metal–ligand interactions, the metal forms a two-dimensional layer pattern.
The structure of the title complex (Fig. 1) is built up from [Ba(C8H5O3Cl2)2(H2O)] polymeric units and solvent water molecules. Each BaII atom binds to nine O donor atoms, seven of which belong to six carboxylate groups and one ether group of five symmetry-related 2,4-dichlorophenoxyacetate ligands, and the remaining two to two water molecules. Thus, the coordination geometry around the BaII atom is a distorted tricapped trigonal prism, in which atoms O3, O5 and O2Wi [symmetry code: (i) −x, y + 1/2, −z + 3/2] form the bottom plane of the trigonal prism and the top plane is completed by atoms O2W, O5i, O2iii [symmetry code: (iii) −x, −y + 2, −z + 1]; the dihedral angle between the planes is 0.509 (5)°. Atoms O1, O4 and O1iii [symmetry code: (iii) −x, y − 1/2, −z + 3/2] cap each quadrilateral face of the trigonal prism (Fig. 2). The Ba—Ocarboxyl lengths (Table 1) range from 2.720 (5) to 3.050 (5) Å, a deviation caused by the asymmetric coordination mode of the 2,4-dichlorophenoxyacetate groups. The chelating modes of the two O atoms from the same 2,4-dichlorophenoxyacetate groups also cause bond-angle deviations from idealized tricapped trigonal prisms. In each ligand, the oxyacetate group and aromatic ring are not perfectly coplanar, the torsion angles being −166.0 (5) [C3—O3—C2—C1] and 168.8 (6)° [C11—O6—C10—C9].
Fig. 3 (omitting some aromatic rings and H atoms) shows the two-dimensional network of the title coordination polymer. The two types of 2,4-dichlorophenoxyacetate ligands are distinguished by two bridging modes; one adopts a tetradentate mode, and the another a tridentate mode. The water molecules and 2,4-dichlorophenoxyacetate ligands are linked to Ba atoms and give one five-membered chelate ring and seven four-membered rings. In such a way, the complex units are assembled into a two-dimensional infinite layer structure parallel to the (100) plane. Within each layer there are also hydrogen bonds involving the coordinated and solvent water molecules (Table 2).