Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802007596/bt6140sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802007596/bt6140Isup2.hkl |
CCDC reference: 185757
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.008 Å
- R factor = 0.031
- wR factor = 0.109
- Data-to-parameter ratio = 16.6
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
PLAT_360 Alert C Short C(sp3)-C(sp3) Bond C(16) - C(17) = 1.41 Ang.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Colorless prismatic crystals of (I) were obtained by slow evaporation from a 50% ethanol–water solution of dipicolinic acid (pyridine-2-carboxylic acid) and LaCl3·7H2O (2:1 molar ratio).
All H atoms were located from difference Fourier maps and included in the refinement using the riding-model approximation.
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation and Rigaku, 1999); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation and Rigaku, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997) and DIRDIF94 (Beurskens et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.
Fig. 1. ORTEPII (Johnson, 1976) drawing of the title compound with the atomic numbering scheme. Ellipsoids for non-H atoms correspond to the 50% probability level. |
[La(C7H4NO4)(C7H3NO4)(H2O)2]·2H2O·C2H6O | F(000) = 1168.0 |
Mr = 588.26 | Dx = 1.863 Mg m−3 |
Monoclinic, P21/a | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -P 2yab | Cell parameters from 25 reflections |
a = 13.037 (4) Å | θ = 14.6–15.0° |
b = 11.003 (3) Å | µ = 2.11 mm−1 |
c = 14.851 (3) Å | T = 296 K |
β = 100.12 (2)° | Pillar, colorless |
V = 2097.2 (10) Å3 | 0.20 × 0.10 × 0.10 mm |
Z = 4 |
Rigaku AFC-5R diffractometer | Rint = 0.025 |
ω–2θ scans | θmax = 27.5° |
Absorption correction: ψ scan (North et al., 1968) | h = 0→16 |
Tmin = 0.773, Tmax = 0.810 | k = 0→14 |
5275 measured reflections | l = −19→18 |
4811 independent reflections | 3 standard reflections every 150 reflections |
3623 reflections with I > 2σ(I) | intensity decay: 0.4% |
Refinement on F2 | H-atom parameters not refined |
R[F2 > 2σ(F2)] = 0.031 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.109 | (Δ/σ)max = 0.003 |
S = 0.80 | Δρmax = 0.98 e Å−3 |
4811 reflections | Δρmin = −0.91 e Å−3 |
289 parameters |
[La(C7H4NO4)(C7H3NO4)(H2O)2]·2H2O·C2H6O | V = 2097.2 (10) Å3 |
Mr = 588.26 | Z = 4 |
Monoclinic, P21/a | Mo Kα radiation |
a = 13.037 (4) Å | µ = 2.11 mm−1 |
b = 11.003 (3) Å | T = 296 K |
c = 14.851 (3) Å | 0.20 × 0.10 × 0.10 mm |
β = 100.12 (2)° |
Rigaku AFC-5R diffractometer | 3623 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.025 |
Tmin = 0.773, Tmax = 0.810 | 3 standard reflections every 150 reflections |
5275 measured reflections | intensity decay: 0.4% |
4811 independent reflections |
R[F2 > 2σ(F2)] = 0.031 | 289 parameters |
wR(F2) = 0.109 | H-atom parameters not refined |
S = 0.80 | Δρmax = 0.98 e Å−3 |
4811 reflections | Δρmin = −0.91 e Å−3 |
Refinement. Refinement using reflections with F2 > 0.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
La1 | 0.15477 (2) | 0.19317 (2) | 0.27207 (1) | 0.01921 (9) | |
O1 | 0.1296 (3) | 0.4954 (3) | 0.4822 (2) | 0.0388 (8) | |
O2 | 0.1405 (3) | 0.3850 (3) | 0.3591 (2) | 0.0338 (7) | |
O3 | 0.1299 (3) | −0.1397 (3) | 0.4671 (3) | 0.0422 (8) | |
O4 | 0.1374 (3) | −0.0192 (3) | 0.3469 (2) | 0.0349 (7) | |
O5 | −0.2093 (2) | 0.1700 (3) | 0.2259 (2) | 0.0324 (7) | |
O6 | −0.0414 (2) | 0.2097 (3) | 0.2798 (2) | 0.0292 (7) | |
O7 | 0.2070 (3) | −0.1112 (3) | 0.0684 (3) | 0.0427 (9) | |
O8 | 0.2172 (2) | 0.0606 (3) | 0.1510 (2) | 0.0327 (7) | |
O9 | 0.3338 (3) | 0.1324 (4) | 0.3589 (3) | 0.0423 (9) | |
O10 | 0.0690 (3) | 0.3164 (3) | 0.1374 (3) | 0.0385 (8) | |
O11 | 0.1136 (4) | −0.3191 (4) | 0.3674 (3) | 0.064 (1) | |
O12 | 0.6134 (3) | 0.0584 (4) | 0.9958 (3) | 0.061 (1) | |
O13 | 0.3601 (3) | 0.1915 (3) | 0.0538 (3) | 0.0372 (8) | |
N1 | 0.1338 (3) | 0.1783 (3) | 0.4481 (3) | 0.0256 (7) | |
N2 | 0.0204 (3) | 0.0465 (3) | 0.1692 (2) | 0.0224 (7) | |
C2 | 0.1314 (4) | 0.2803 (4) | 0.4962 (3) | 0.0274 (9) | |
C3 | 0.1252 (5) | 0.2788 (5) | 0.5883 (4) | 0.042 (1) | |
C4 | 0.1243 (6) | 0.1673 (6) | 0.6313 (4) | 0.053 (2) | |
C5 | 0.1272 (4) | 0.0611 (5) | 0.5813 (3) | 0.042 (1) | |
C6 | 0.1316 (3) | 0.0713 (4) | 0.4906 (3) | 0.0280 (9) | |
C7 | 0.1334 (3) | 0.3960 (4) | 0.4423 (3) | 0.0266 (9) | |
C8 | 0.1337 (3) | −0.0352 (4) | 0.4282 (3) | 0.0301 (9) | |
C9 | −0.0812 (3) | 0.0476 (4) | 0.1748 (3) | 0.0217 (8) | |
C10 | −0.1508 (3) | −0.0397 (4) | 0.1341 (3) | 0.0286 (9) | |
C11 | −0.1124 (4) | −0.1333 (5) | 0.0874 (4) | 0.036 (1) | |
C12 | −0.0086 (4) | −0.1352 (4) | 0.0805 (3) | 0.034 (1) | |
C13 | 0.0555 (3) | −0.0426 (4) | 0.1211 (3) | 0.0249 (8) | |
C14 | −0.1139 (3) | 0.1509 (4) | 0.2305 (3) | 0.0226 (8) | |
C15 | 0.1696 (3) | −0.0311 (4) | 0.1126 (3) | 0.0267 (9) | |
C16 | 0.023 (1) | −0.401 (1) | 0.2188 (9) | 0.179 (8) | |
C17 | 0.107 (2) | −0.340 (1) | 0.2731 (10) | 0.151 (5) | |
H1 | 0.1382 | −0.1938 | 0.4311 | 0.0633* | |
H3 | 0.1220 | 0.3507 | 0.6205 | 0.0520* | |
H4 | 0.1216 | 0.1637 | 0.6933 | 0.0660* | |
H5 | 0.1261 | −0.0147 | 0.6090 | 0.0527* | |
H9A | 0.3386 | 0.0864 | 0.4028 | 0.2247* | |
H9B | 0.3893 | 0.1641 | 0.3541 | 0.2247* | |
H10 | −0.2211 | −0.0355 | 0.1380 | 0.0357* | |
H10A | 0.0056 | 0.3140 | 0.1356 | 0.2247* | |
H10B | 0.0837 | 0.3424 | 0.0895 | 0.2247* | |
H11 | −0.1566 | −0.1948 | 0.0608 | 0.0451* | |
H12 | 0.0181 | −0.1976 | 0.0492 | 0.0422* | |
H12A | 0.5959 | −0.0119 | 0.9889 | 0.2247* | |
H12B | 0.6662 | 0.0795 | 0.9786 | 0.2247* | |
H13 | 0.1178 | −0.3844 | 0.3944 | 0.0955* | |
H13A | 0.3185 | 0.1438 | 0.0673 | 0.2247* | |
H13B | 0.3404 | 0.2467 | 0.0197 | 0.2247* | |
H16A | 0.0106 | −0.4765 | 0.2479 | 0.2217* | |
H16B | 0.0393 | −0.4178 | 0.1594 | 0.2217* | |
H16C | −0.0381 | −0.3513 | 0.2125 | 0.2217* | |
H17A | 0.1705 | −0.3840 | 0.2660 | 0.1872* | |
H17B | 0.1128 | −0.2608 | 0.2448 | 0.1872* |
U11 | U22 | U33 | U12 | U13 | U23 | |
La1 | 0.0159 (1) | 0.0202 (1) | 0.0222 (1) | −0.00145 (9) | 0.00523 (8) | −0.00013 (9) |
O1 | 0.056 (2) | 0.027 (2) | 0.034 (2) | 0.000 (2) | 0.010 (2) | −0.008 (1) |
O2 | 0.048 (2) | 0.024 (2) | 0.031 (2) | −0.004 (1) | 0.011 (1) | −0.002 (1) |
O3 | 0.054 (2) | 0.026 (2) | 0.049 (2) | −0.001 (2) | 0.013 (2) | 0.010 (2) |
O4 | 0.046 (2) | 0.028 (2) | 0.032 (2) | −0.004 (1) | 0.010 (1) | −0.001 (1) |
O5 | 0.016 (1) | 0.040 (2) | 0.043 (2) | 0.004 (1) | 0.010 (1) | −0.008 (1) |
O6 | 0.017 (1) | 0.035 (2) | 0.035 (2) | 0.000 (1) | 0.005 (1) | −0.009 (1) |
O7 | 0.034 (2) | 0.041 (2) | 0.058 (2) | 0.003 (2) | 0.021 (2) | −0.018 (2) |
O8 | 0.024 (1) | 0.034 (2) | 0.042 (2) | −0.006 (1) | 0.015 (1) | −0.016 (1) |
O9 | 0.024 (2) | 0.054 (2) | 0.048 (2) | −0.001 (2) | 0.003 (1) | 0.025 (2) |
O10 | 0.028 (2) | 0.042 (2) | 0.044 (2) | −0.002 (1) | 0.003 (1) | 0.017 (2) |
O11 | 0.102 (4) | 0.032 (2) | 0.055 (3) | 0.003 (2) | 0.008 (3) | 0.006 (2) |
O12 | 0.052 (2) | 0.056 (3) | 0.083 (3) | −0.004 (2) | 0.035 (2) | −0.026 (2) |
O13 | 0.030 (2) | 0.042 (2) | 0.040 (2) | −0.005 (1) | 0.009 (1) | −0.001 (2) |
N1 | 0.023 (2) | 0.025 (2) | 0.029 (2) | 0.000 (1) | 0.007 (1) | 0.003 (1) |
N2 | 0.019 (2) | 0.023 (2) | 0.026 (2) | 0.000 (1) | 0.007 (1) | −0.001 (1) |
C2 | 0.026 (2) | 0.029 (2) | 0.028 (2) | −0.004 (2) | 0.007 (2) | 0.000 (2) |
C3 | 0.053 (3) | 0.047 (3) | 0.027 (2) | −0.004 (2) | 0.013 (2) | −0.003 (2) |
C4 | 0.075 (4) | 0.057 (4) | 0.029 (3) | −0.003 (3) | 0.016 (3) | 0.007 (2) |
C5 | 0.051 (3) | 0.043 (3) | 0.034 (3) | 0.001 (2) | 0.012 (2) | 0.014 (2) |
C6 | 0.022 (2) | 0.028 (2) | 0.034 (2) | 0.000 (2) | 0.007 (2) | 0.010 (2) |
C7 | 0.028 (2) | 0.023 (2) | 0.028 (2) | −0.003 (2) | 0.003 (2) | −0.003 (2) |
C8 | 0.028 (2) | 0.024 (2) | 0.039 (2) | 0.004 (2) | 0.008 (2) | 0.009 (2) |
C9 | 0.016 (2) | 0.024 (2) | 0.024 (2) | 0.001 (1) | 0.003 (1) | 0.001 (2) |
C10 | 0.018 (2) | 0.031 (2) | 0.037 (2) | −0.003 (2) | 0.004 (2) | −0.001 (2) |
C11 | 0.025 (2) | 0.032 (2) | 0.049 (3) | −0.005 (2) | 0.002 (2) | −0.014 (2) |
C12 | 0.032 (2) | 0.030 (2) | 0.039 (3) | 0.000 (2) | 0.007 (2) | −0.010 (2) |
C13 | 0.024 (2) | 0.023 (2) | 0.029 (2) | 0.004 (2) | 0.007 (2) | 0.000 (2) |
C14 | 0.017 (2) | 0.026 (2) | 0.026 (2) | 0.001 (2) | 0.007 (1) | 0.003 (2) |
C15 | 0.024 (2) | 0.030 (2) | 0.028 (2) | 0.004 (2) | 0.009 (2) | −0.004 (2) |
C16 | 0.32 (2) | 0.071 (7) | 0.103 (8) | 0.015 (10) | −0.09 (1) | −0.012 (6) |
C17 | 0.23 (2) | 0.095 (9) | 0.12 (1) | 0.04 (1) | 0.01 (1) | 0.022 (7) |
La1—O2 | 2.499 (3) | N1—C2 | 1.334 (6) |
La1—O4 | 2.615 (3) | N1—C6 | 1.338 (6) |
La1—O5i | 2.511 (3) | N2—C9 | 1.341 (5) |
La1—O6 | 2.586 (3) | N2—C13 | 1.340 (6) |
La1—O8 | 2.557 (4) | C2—C3 | 1.385 (7) |
La1—O9 | 2.549 (3) | C2—C7 | 1.506 (6) |
La1—O10 | 2.511 (4) | C3—C4 | 1.383 (9) |
La1—N1 | 2.681 (4) | C3—H3 | 0.929 |
La1—N2 | 2.659 (3) | C4—C5 | 1.388 (8) |
O1—C7 | 1.250 (6) | C4—H4 | 0.929 |
O2—C7 | 1.261 (6) | C5—C6 | 1.364 (7) |
O3—C8 | 1.291 (6) | C5—H5 | 0.930 |
O3—H1 | 0.820 | C6—C8 | 1.497 (7) |
O4—C8 | 1.229 (6) | C9—C10 | 1.386 (6) |
O5—C14 | 1.251 (5) | C9—C14 | 1.510 (6) |
O6—C14 | 1.267 (5) | C10—C11 | 1.384 (7) |
O7—C15 | 1.248 (6) | C10—H10 | 0.930 |
O8—C15 | 1.266 (5) | C11—C12 | 1.375 (7) |
O9—H9A | 0.820 | C11—H11 | 0.930 |
O9—H9B | 0.817 | C12—C13 | 1.387 (6) |
O10—H10A | 0.823 | C12—H12 | 0.929 |
O10—H10B | 0.819 | C13—C15 | 1.520 (6) |
O11—C17 | 1.41 (2) | C16—C17 | 1.41 (2) |
O11—H13 | 0.820 | C16—H16A | 0.961 |
O12—H12A | 0.808 | C16—H16B | 0.961 |
O12—H12B | 0.809 | C16—H16C | 0.957 |
O13—H13A | 0.804 | C17—H17A | 0.986 |
O13—H13B | 0.804 | C17—H17B | 0.977 |
La1···O4 | 2.615 (3) | O5···O13vii | 3.238 (5) |
La1···O5i | 2.511 (3) | O5···O8vii | 3.251 (4) |
La1···O6 | 2.586 (3) | O6···O9vii | 2.778 (5) |
La1···O8 | 2.557 (4) | O6···O13vii | 3.547 (5) |
La1···O9 | 2.549 (3) | O7···O12viii | 2.741 (6) |
La1···O10 | 2.511 (4) | O7···O13ix | 2.865 (5) |
La1···N1 | 2.681 (4) | O7···C10x | 3.400 (6) |
La1···N2 | 2.659 (3) | O10···O12xi | 2.660 (6) |
O1···O11ii | 2.644 (6) | O10···O13vii | 2.789 (5) |
O1···O9iii | 2.770 (5) | O10···C16ii | 3.43 (1) |
O1···C8iii | 3.157 (6) | O11···C7xii | 3.321 (6) |
O1···C6iii | 3.180 (6) | O11···C3vi | 3.323 (9) |
O1···O3iii | 3.432 (5) | O11···C4v | 3.417 (9) |
O1···O1iv | 3.513 (8) | O11···C3v | 3.521 (8) |
O1···C5iii | 3.538 (7) | O11···C4vi | 3.526 (9) |
O1···C17ii | 3.56 (1) | O11···C5v | 3.582 (8) |
O2···O11ii | 3.279 (5) | O12···O13viii | 2.883 (6) |
O2···C17ii | 3.28 (1) | O12···O12xiii | 3.247 (9) |
O2···C16ii | 3.33 (1) | O12···C16iii | 3.39 (1) |
O2···C5iii | 3.574 (6) | O12···C15viii | 3.505 (7) |
O3···C7v | 3.167 (6) | O12···C10xiv | 3.551 (6) |
O3···C2v | 3.188 (6) | O13···C12xv | 3.566 (6) |
O3···C4vi | 3.392 (8) | O13···C11x | 3.586 (6) |
O3···C5vi | 3.413 (7) | C4···C17iii | 3.55 (2) |
O3···C3v | 3.549 (8) | C5···C8vi | 3.391 (7) |
O3···O9v | 3.572 (5) | C7···C8iii | 3.382 (6) |
O5···O9vii | 2.925 (5) | C11···C15x | 3.446 (7) |
O5···O10vii | 2.961 (4) | C12···C13x | 3.539 (6) |
O2—La1—O4 | 121.0 (1) | C9—N2—C13 | 118.3 (3) |
O2—La1—O5i | 75.8 (1) | N1—C2—C3 | 122.0 (4) |
O2—La1—O6 | 75.7 (1) | N1—C2—C7 | 115.0 (4) |
O2—La1—O8 | 155.2 (1) | C3—C2—C7 | 123.1 (4) |
O2—La1—O9 | 96.0 (1) | C2—C3—C4 | 118.3 (5) |
O2—La1—O10 | 83.8 (1) | C2—C3—H3 | 120.8 |
O2—La1—N1 | 61.2 (1) | C4—C3—H3 | 120.9 |
O2—La1—N2 | 135.1 (1) | C3—C4—C5 | 119.8 (5) |
O4—La1—O5i | 140.4 (1) | C3—C4—H4 | 120.0 |
O4—La1—O6 | 83.3 (1) | C5—C4—H4 | 120.2 |
O4—La1—O8 | 81.4 (1) | C4—C5—C6 | 117.9 (5) |
O4—La1—O9 | 72.0 (1) | C4—C5—H5 | 121.0 |
O4—La1—O10 | 139.6 (1) | C6—C5—H5 | 121.1 |
O4—La1—N1 | 60.0 (1) | N1—C6—C5 | 123.1 (4) |
O4—La1—N2 | 66.71 (10) | N1—C6—C8 | 113.2 (4) |
O5i—La1—O6 | 136.10 (10) | C5—C6—C8 | 123.7 (4) |
O5i—La1—O8 | 79.8 (1) | O1—C7—O2 | 124.4 (4) |
O5i—La1—O9 | 70.6 (1) | O1—C7—C2 | 118.8 (4) |
O5i—La1—O10 | 72.2 (1) | O2—C7—C2 | 116.9 (4) |
O5i—La1—N1 | 120.1 (1) | O3—C8—O4 | 125.4 (4) |
O5i—La1—N2 | 129.2 (1) | O3—C8—C6 | 114.4 (4) |
O6—La1—O8 | 120.69 (10) | O4—C8—C6 | 120.2 (4) |
O6—La1—O9 | 145.2 (1) | N2—C9—C10 | 123.0 (4) |
O6—La1—O10 | 72.1 (1) | N2—C9—C14 | 114.7 (3) |
O6—La1—N1 | 72.0 (1) | C10—C9—C14 | 122.3 (4) |
O6—La1—N2 | 60.7 (1) | C9—C10—C11 | 117.9 (4) |
O8—La1—O9 | 80.2 (1) | C9—C10—H10 | 121.0 |
O8—La1—O10 | 84.3 (1) | C11—C10—H10 | 121.1 |
O8—La1—N1 | 138.6 (1) | C10—C11—C12 | 119.8 (4) |
O8—La1—N2 | 60.6 (1) | C10—C11—H11 | 120.1 |
O9—La1—O10 | 141.7 (1) | C12—C11—H11 | 120.1 |
O9—La1—N1 | 74.5 (1) | C11—C12—C13 | 118.8 (5) |
O9—La1—N2 | 125.7 (1) | C11—C12—H12 | 120.6 |
O10—La1—N1 | 134.6 (1) | C13—C12—H12 | 120.6 |
O10—La1—N2 | 73.4 (1) | N2—C13—C12 | 122.2 (4) |
N1—La1—N2 | 110.7 (1) | N2—C13—C15 | 114.5 (4) |
La1—O2—C7 | 127.8 (3) | C12—C13—C15 | 123.3 (4) |
C8—O3—H1 | 109.5 | O5—C14—O6 | 125.4 (4) |
La1—O4—C8 | 124.6 (3) | O5—C14—C9 | 118.0 (3) |
La1vii—O5—C14 | 145.9 (3) | O6—C14—C9 | 116.5 (4) |
La1—O6—C14 | 125.6 (3) | O7—C15—O8 | 126.5 (4) |
La1—O8—C15 | 125.5 (3) | O7—C15—C13 | 117.6 (4) |
La1—O9—H9A | 120.0 | O8—C15—C13 | 116.0 (4) |
La1—O9—H9B | 126.2 | C17—C16—H16A | 109.1 |
H9A—O9—H9B | 112.8 | C17—C16—H16B | 110.0 |
La1—O10—H10A | 108.2 | C17—C16—H16C | 109.2 |
La1—O10—H10B | 137.8 | H16A—C16—H16B | 109.3 |
H10A—O10—H10B | 111.7 | H16A—C16—H16C | 109.6 |
C17—O11—H13 | 109.3 | H16B—C16—H16C | 109.6 |
H12A—O12—H12B | 118.1 | O11—C17—C16 | 123 (1) |
H13A—O13—H13B | 119.7 | O11—C17—H17A | 106.2 |
La1—N1—C2 | 119.1 (3) | O11—C17—H17B | 106.7 |
La1—N1—C6 | 121.8 (3) | C16—C17—H17A | 106.8 |
C2—N1—C6 | 118.9 (4) | C16—C17—H17B | 107.1 |
La1—N2—C9 | 121.1 (3) | H17A—C17—H17B | 104.8 |
La1—N2—C13 | 119.8 (3) | ||
La1—O2—C7—O1 | 177.8 (3) | O8—La1—O2—C7 | −145.9 (3) |
La1—O2—C7—C2 | −1.2 (6) | O8—La1—O4—C8 | 160.0 (4) |
La1—O4—C8—O3 | −176.7 (3) | O8—La1—O6—C14 | 4.3 (4) |
La1—O4—C8—C6 | 4.3 (6) | O8—La1—N1—C2 | 157.1 (3) |
La1—O6—C14—O5 | −170.3 (3) | O8—La1—N1—C6 | −19.0 (4) |
La1—O6—C14—C9 | 11.2 (5) | O8—La1—N2—C9 | −174.8 (3) |
La1—O8—C15—O7 | −164.1 (4) | O8—La1—N2—C13 | 15.4 (3) |
La1—O8—C15—C13 | 16.6 (5) | O8—C15—C13—N2 | −0.4 (6) |
La1—N1—C2—C3 | −177.1 (4) | O8—C15—C13—C12 | 177.8 (4) |
La1—N1—C2—C7 | 4.1 (5) | O9—La1—O2—C7 | −66.2 (4) |
La1—N1—C6—C5 | 176.0 (4) | O9—La1—O4—C8 | 77.6 (4) |
La1—N1—C6—C8 | −4.4 (5) | O9—La1—O6—C14 | −116.1 (3) |
La1—N2—C9—C10 | −169.2 (3) | O9—La1—O8—C15 | 124.1 (3) |
La1—N2—C9—C14 | 9.8 (4) | O9—La1—N1—C2 | 102.8 (3) |
La1—N2—C13—C12 | 167.5 (3) | O9—La1—N1—C6 | −73.4 (3) |
La1—N2—C13—C15 | −14.3 (5) | O9—La1—N2—C9 | 135.5 (3) |
O1—C7—C2—N1 | 178.8 (4) | O9—La1—N2—C13 | −34.3 (4) |
O1—C7—C2—C3 | 0.1 (7) | O10—La1—O2—C7 | 152.3 (4) |
O2—La1—O4—C8 | −8.5 (4) | O10—La1—O4—C8 | −129.4 (3) |
O2—La1—O6—C14 | 164.0 (3) | O10—La1—O6—C14 | 76.0 (3) |
O2—La1—O8—C15 | −152.8 (3) | O10—La1—O8—C15 | −91.1 (3) |
O2—La1—N1—C2 | −3.3 (3) | O10—La1—N1—C2 | −47.6 (4) |
O2—La1—N1—C6 | −179.5 (3) | O10—La1—N1—C6 | 136.2 (3) |
O2—La1—N2—C9 | −19.3 (4) | O10—La1—N2—C9 | −82.0 (3) |
O2—La1—N2—C13 | 170.9 (3) | O10—La1—N2—C13 | 108.2 (3) |
O2—C7—C2—N1 | −2.2 (6) | N1—La1—O2—C7 | 2.3 (3) |
O2—C7—C2—C3 | 179.1 (5) | N1—La1—O4—C8 | −4.5 (3) |
O3—C8—C6—N1 | −178.9 (4) | N1—La1—O6—C14 | −132.1 (3) |
O3—C8—C6—C5 | 0.7 (6) | N1—La1—O8—C15 | 71.5 (4) |
O4—La1—O2—C7 | 6.3 (4) | N1—La1—N2—C9 | 50.1 (3) |
O4—La1—O6—C14 | −71.6 (3) | N1—La1—N2—C13 | −119.7 (3) |
O4—La1—O8—C15 | 51.1 (3) | N1—C2—C3—C4 | 1.6 (8) |
O4—La1—N1—C2 | −179.4 (3) | N1—C6—C5—C4 | 0.3 (8) |
O4—La1—N1—C6 | 4.5 (3) | N2—La1—O2—C7 | 93.4 (4) |
O4—La1—N2—C9 | 91.9 (3) | N2—La1—O4—C8 | −138.4 (4) |
O4—La1—N2—C13 | −77.9 (3) | N2—La1—O6—C14 | −4.6 (3) |
O4—C8—C6—N1 | 0.2 (6) | N2—La1—O8—C15 | −17.0 (3) |
O4—C8—C6—C5 | 179.8 (5) | N2—La1—N1—C2 | −134.3 (3) |
O5—La1vii—O2vii—C7vii | 134.5 (4) | N2—La1—N1—C6 | 49.5 (3) |
O5—La1vii—O4vii—C8vii | −97.6 (4) | N2—C9—C10—C11 | 1.4 (7) |
O5—La1vii—O6vii—C14vii | −113.0 (3) | N2—C13—C12—C11 | 2.2 (7) |
O5—La1vii—O8vii—C15vii | 164.0 (3) | C2—N1—C6—C5 | −0.1 (7) |
O5—La1vii—N1vii—C2vii | −46.8 (3) | C2—N1—C6—C8 | 179.4 (4) |
O5—La1vii—N1vii—C6vii | 129.4 (3) | C2—C3—C4—C5 | −1.3 (9) |
O5—La1vii—N2vii—C9vii | 131.1 (3) | C3—C2—N1—C6 | −0.9 (7) |
O5—La1vii—N2vii—C13vii | −59.1 (3) | C3—C4—C5—C6 | 0.4 (9) |
O5—C14—C9—N2 | 168.0 (4) | C4—C3—C2—C7 | −179.8 (5) |
O5—C14—C9—C10 | −13.0 (6) | C4—C5—C6—C8 | −179.2 (5) |
O6—La1—O2—C7 | 79.3 (4) | C6—N1—C2—C7 | −179.6 (4) |
O6—La1—O4—C8 | −77.5 (4) | C9—N2—C13—C12 | −2.6 (6) |
O6—La1—O8—C15 | −25.9 (4) | C9—N2—C13—C15 | 175.6 (4) |
O6—La1—N1—C2 | −86.6 (3) | C9—C10—C11—C12 | −1.9 (7) |
O6—La1—N1—C6 | 97.2 (3) | C10—C9—N2—C13 | 0.8 (6) |
O6—La1—N2—C9 | −3.6 (3) | C10—C11—C12—C13 | 0.2 (7) |
O6—La1—N2—C13 | −173.4 (3) | C11—C10—C9—C14 | −177.5 (4) |
O6—C14—C9—N2 | −13.4 (5) | C11—C12—C13—C15 | −175.9 (4) |
O6—C14—C9—C10 | 165.7 (4) | C13—N2—C9—C14 | 179.8 (4) |
O7—C15—C13—N2 | −179.8 (4) | C13—N2—C9—C14 | 179.8 (4) |
O7—C15—C13—C12 | −1.6 (6) |
Symmetry codes: (i) x+1/2, −y+1/2, z; (ii) x, y+1, z; (iii) −x+1/2, y+1/2, −z+1; (iv) −x, −y+1, −z+1; (v) −x+1/2, y−1/2, −z+1; (vi) −x, −y, −z+1; (vii) x−1/2, −y+1/2, z; (viii) −x+1, −y, −z+1; (ix) −x+1/2, y−1/2, −z; (x) −x, −y, −z; (xi) x−1/2, −y+1/2, z−1; (xii) x, y−1, z; (xiii) −x+1, −y, −z+2; (xiv) x+1, y, z+1; (xv) −x+1/2, y+1/2, −z. |
Experimental details
Crystal data | |
Chemical formula | [La(C7H4NO4)(C7H3NO4)(H2O)2]·2H2O·C2H6O |
Mr | 588.26 |
Crystal system, space group | Monoclinic, P21/a |
Temperature (K) | 296 |
a, b, c (Å) | 13.037 (4), 11.003 (3), 14.851 (3) |
β (°) | 100.12 (2) |
V (Å3) | 2097.2 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.11 |
Crystal size (mm) | 0.20 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Rigaku AFC-5R diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.773, 0.810 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5275, 4811, 3623 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.109, 0.80 |
No. of reflections | 4811 |
No. of parameters | 289 |
No. of restraints | ? |
H-atom treatment | H-atom parameters not refined |
Δρmax, Δρmin (e Å−3) | 0.98, −0.91 |
Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation and Rigaku, 1999), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation and Rigaku, 1999), SHELXS97 (Sheldrick, 1997) and DIRDIF94 (Beurskens et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), TEXSAN.
La1—O2 | 2.499 (3) | N1—C2 | 1.334 (6) |
La1—O4 | 2.615 (3) | N1—C6 | 1.338 (6) |
La1—O5i | 2.511 (3) | N2—C9 | 1.341 (5) |
La1—O6 | 2.586 (3) | N2—C13 | 1.340 (6) |
La1—O8 | 2.557 (4) | C2—C3 | 1.385 (7) |
La1—O9 | 2.549 (3) | C2—C7 | 1.506 (6) |
La1—O10 | 2.511 (4) | C3—C4 | 1.383 (9) |
La1—N1 | 2.681 (4) | C4—C5 | 1.388 (8) |
La1—N2 | 2.659 (3) | C5—C6 | 1.364 (7) |
O1—C7 | 1.250 (6) | C6—C8 | 1.497 (7) |
O2—C7 | 1.261 (6) | C9—C10 | 1.386 (6) |
O3—C8 | 1.291 (6) | C9—C14 | 1.510 (6) |
O4—C8 | 1.229 (6) | C10—C11 | 1.384 (7) |
O5—C14 | 1.251 (5) | C11—C12 | 1.375 (7) |
O6—C14 | 1.267 (5) | C12—C13 | 1.387 (6) |
O7—C15 | 1.248 (6) | C13—C15 | 1.520 (6) |
O8—C15 | 1.266 (5) | C16—C17 | 1.41 (2) |
O11—C17 | 1.41 (2) | ||
O2—La1—O4 | 121.0 (1) | O5i—La1—N1 | 120.1 (1) |
O2—La1—O5i | 75.8 (1) | O5i—La1—N2 | 129.2 (1) |
O2—La1—O6 | 75.7 (1) | O6—La1—O8 | 120.69 (10) |
O2—La1—O8 | 155.2 (1) | O6—La1—O9 | 145.2 (1) |
O2—La1—O9 | 96.0 (1) | O6—La1—O10 | 72.1 (1) |
O2—La1—O10 | 83.8 (1) | O6—La1—N1 | 72.0 (1) |
O2—La1—N1 | 61.2 (1) | O6—La1—N2 | 60.7 (1) |
O2—La1—N2 | 135.1 (1) | O8—La1—O9 | 80.2 (1) |
O4—La1—O5i | 140.4 (1) | O8—La1—O10 | 84.3 (1) |
O4—La1—O6 | 83.3 (1) | O8—La1—N1 | 138.6 (1) |
O4—La1—O8 | 81.4 (1) | O8—La1—N2 | 60.6 (1) |
O4—La1—O9 | 72.0 (1) | O9—La1—O10 | 141.7 (1) |
O4—La1—O10 | 139.6 (1) | O9—La1—N1 | 74.5 (1) |
O4—La1—N1 | 60.0 (1) | O9—La1—N2 | 125.7 (1) |
O4—La1—N2 | 66.71 (10) | O10—La1—N1 | 134.6 (1) |
O5i—La1—O6 | 136.10 (10) | O10—La1—N2 | 73.4 (1) |
O5i—La1—O8 | 79.8 (1) | N1—La1—N2 | 110.7 (1) |
O5i—La1—O9 | 70.6 (1) | La1—O2—C7 | 127.8 (3) |
O5i—La1—O10 | 72.2 (1) |
Symmetry code: (i) x+1/2, −y+1/2, z. |
Dipicolinic acid (dipic; pyridine-2,6-dicarboxylic acid) is a component of bacterial spores (Powell, 1953). It can induce apoptosis in leukemia HL-60 cells which is cell-death characterized by DNA fragmentation (Ogata et al., 2000). It forms complexes with many bivalent and monovalent metals, such as CaII, TiII, MnII, FeII, NiII, CuII, ZnII, SrII, AgII and LiI (Odoko et al., 2002). Here, we aimed to clarify the structure of the rare earth metal complexes of dipicolinic acid, since rare earth metals are known to have antitumor activity (Zhou et al., 2001). In this study, the structure of the LaIII complex (I) has been determined.
The structure of (I) is shown in Fig. 1. It has a unique polynuclear chain structure consisting of the [LaIII(dipic)2(H2O)2] coordination unit, in which the central LaIII atom is bonded to four O atoms and two N atoms of the two N,O,O'-tridentate dipicolinates and to two water O atoms. The LaIII ions in the coordination units are linked together by the carboxylate O atom of the dianionic dipicolinate ligand, forming a polynuclear chain structure. One of the ligand molecules is dianionic and another is monoanionic. The total charge of the title compound is neutral. In the [LaIII(dipic)2] unit, LaIII has a distorted nine-coordinate geometry. Selected geometric parameters are listed in Table 1.