Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680504122X/ww6432sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680504122X/ww6432Isup2.hkl |
CCDC reference: 296698
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.005 Å
- R factor = 0.056
- wR factor = 0.144
- Data-to-parameter ratio = 15.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.11 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Ca1 PLAT417_ALERT_2_C Short Inter D-H..H-D H40B .. H50B .. 2.10 Ang. PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.12 Ratio
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
N-Succinopyridine was prepared according to the procedures of Kostyanovsky et al. (2003) and Kotov et al. (2001). The sodium salt NaL was obtained by neutralization of HL with NaOH in aqueous solution and recrystallization in water. Compound (I) was prepared by reaction of NaL (0.217 mg, 1 mmol) and CaCl2·6H2O in distilled water (5 ml). Crystals of (I) suitable for X-ray structure analysis were obtained by standing the reaction mixture for several days at ambient temperature.
All H atoms were located on the difference Fourier map and allowed to ride on their respective parent atoms. For the CH and CH2 groups, Uiso(H) values were set equal to 1.2Ueq(carrier atom) and for the water molecules, they were set equal to 1.5Ueq(carrier atom).
Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: XSCANS; 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.
[Ca(C9H8NO4)2(H2O)2]·2.5H2O | F(000) = 2136 |
Mr = 509.48 | Dx = 1.559 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 40 reflections |
a = 31.766 (14) Å | θ = 9.3–25.8° |
b = 9.8281 (13) Å | µ = 0.36 mm−1 |
c = 14.2746 (16) Å | T = 294 K |
β = 103.018 (16)° | Block, colorless |
V = 4342 (2) Å3 | 0.28 × 0.22 × 0.20 mm |
Z = 8 |
Siemens P4 diffractometer | 3569 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.036 |
Graphite monochromator | θmax = 27.0°, θmin = 2.2° |
ω scans | h = −1→40 |
Absorption correction: ψ scan (North et al., 1968) | k = −1→12 |
Tmin = 0.909, Tmax = 0.930 | l = −18→17 |
5549 measured reflections | 3 standard reflections every 120 reflections |
4744 independent reflections | intensity decay: 8% |
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)] = 0.056 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.144 | H-atom parameters constrained |
S = 1.13 | w = 1/[σ2(Fo2) + (0.0429P)2 + 15.5672P] where P = (Fo2 + 2Fc2)/3 |
4744 reflections | (Δ/σ)max < 0.001 |
303 parameters | Δρmax = 0.44 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
[Ca(C9H8NO4)2(H2O)2]·2.5H2O | V = 4342 (2) Å3 |
Mr = 509.48 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 31.766 (14) Å | µ = 0.36 mm−1 |
b = 9.8281 (13) Å | T = 294 K |
c = 14.2746 (16) Å | 0.28 × 0.22 × 0.20 mm |
β = 103.018 (16)° |
Siemens P4 diffractometer | 3569 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.036 |
Tmin = 0.909, Tmax = 0.930 | 3 standard reflections every 120 reflections |
5549 measured reflections | intensity decay: 8% |
4744 independent reflections |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.144 | H-atom parameters constrained |
S = 1.13 | w = 1/[σ2(Fo2) + (0.0429P)2 + 15.5672P] where P = (Fo2 + 2Fc2)/3 |
4744 reflections | Δρmax = 0.44 e Å−3 |
303 parameters | Δρmin = −0.32 e Å−3 |
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 > 2σ(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 | ||
Ca1 | 0.10310 (2) | 0.85722 (6) | 0.11548 (4) | 0.02100 (16) | |
O1W | 0.17903 (8) | 0.8520 (3) | 0.1582 (2) | 0.0578 (9) | |
H10A | 0.2008 | 0.8030 | 0.1465 | 0.087* | |
H10B | 0.1886 | 0.9348 | 0.1953 | 0.087* | |
O2W | 0.03000 (8) | 0.8373 (3) | 0.13758 (18) | 0.0407 (6) | |
H20A | 0.0225 | 0.7773 | 0.1688 | 0.061* | |
H20B | 0.0040 | 0.8684 | 0.1147 | 0.061* | |
O3W | 0.0000 | 0.6206 (4) | 0.2500 | 0.0400 (8) | |
H30A | −0.0191 | 0.5599 | 0.2179 | 0.060* | |
O4W | 0.25432 (8) | 0.8002 (3) | −0.1230 (2) | 0.0455 (7) | |
H40A | 0.2298 | 0.8366 | −0.1524 | 0.068* | |
H40B | 0.2626 | 0.8451 | −0.0733 | 0.068* | |
O5W | 0.23427 (9) | 0.4527 (3) | 0.4536 (2) | 0.0528 (7) | |
H50A | 0.2112 | 0.4896 | 0.4096 | 0.079* | |
H50B | 0.2343 | 0.3685 | 0.4259 | 0.079* | |
O1 | 0.09401 (8) | 0.6924 (2) | −0.00371 (15) | 0.0308 (5) | |
O2 | 0.06406 (8) | 0.5464 (2) | −0.11898 (15) | 0.0298 (5) | |
C1 | 0.08151 (10) | 0.6563 (3) | −0.0905 (2) | 0.0212 (6) | |
C2 | 0.08985 (10) | 0.7640 (3) | −0.16370 (19) | 0.0207 (6) | |
H2A | 0.0771 | 0.8497 | −0.1486 | 0.031* | |
O3 | 0.18469 (8) | 0.9338 (3) | −0.2195 (2) | 0.0496 (8) | |
O4 | 0.11479 (7) | 0.9771 (2) | −0.26199 (16) | 0.0306 (5) | |
C3 | 0.14634 (10) | 0.9096 (3) | −0.2186 (2) | 0.0256 (7) | |
C4 | 0.13776 (10) | 0.7901 (3) | −0.1560 (2) | 0.0244 (6) | |
H4A | 0.1508 | 0.7085 | −0.1751 | 0.029* | |
H4B | 0.1515 | 0.8087 | −0.0894 | 0.029* | |
N1 | 0.06770 (8) | 0.7259 (2) | −0.26315 (16) | 0.0198 (5) | |
C5 | 0.03723 (10) | 0.8091 (3) | −0.3143 (2) | 0.0243 (6) | |
H5A | 0.0311 | 0.8909 | −0.2875 | 0.029* | |
C6 | 0.01534 (10) | 0.7751 (3) | −0.4043 (2) | 0.0285 (7) | |
H6A | −0.0060 | 0.8322 | −0.4385 | 0.034* | |
C7 | 0.02524 (11) | 0.6544 (4) | −0.4447 (2) | 0.0302 (7) | |
H7A | 0.0105 | 0.6295 | −0.5062 | 0.036* | |
C8 | 0.05714 (11) | 0.5715 (3) | −0.3930 (2) | 0.0282 (7) | |
H8A | 0.0644 | 0.4909 | −0.4197 | 0.034* | |
C9 | 0.07825 (10) | 0.6093 (3) | −0.3013 (2) | 0.0233 (6) | |
H9A | 0.0998 | 0.5539 | −0.2658 | 0.028* | |
O5 | 0.11345 (8) | 0.6873 (2) | 0.23276 (15) | 0.0336 (6) | |
O6 | 0.16197 (9) | 0.5620 (3) | 0.33267 (17) | 0.0400 (6) | |
C10 | 0.13792 (10) | 0.6617 (3) | 0.3132 (2) | 0.0250 (6) | |
C11 | 0.13551 (10) | 0.7675 (3) | 0.3923 (2) | 0.0232 (6) | |
H11A | 0.1486 | 0.8518 | 0.3757 | 0.035* | |
O7 | 0.11610 (10) | 0.9750 (3) | 0.5084 (2) | 0.0539 (8) | |
O8 | 0.04608 (10) | 0.9668 (3) | 0.4507 (3) | 0.0590 (9) | |
C12 | 0.08327 (12) | 0.9224 (3) | 0.4563 (3) | 0.0343 (8) | |
C13 | 0.08896 (10) | 0.8001 (3) | 0.3955 (2) | 0.0272 (7) | |
H13A | 0.0726 | 0.8157 | 0.3303 | 0.033* | |
H13B | 0.0766 | 0.7212 | 0.4200 | 0.033* | |
C14 | 0.19645 (11) | 0.7932 (4) | 0.5320 (3) | 0.0344 (8) | |
H14A | 0.2041 | 0.8726 | 0.5045 | 0.041* | |
N2 | 0.16145 (8) | 0.7216 (3) | 0.48709 (17) | 0.0233 (5) | |
C15 | 0.22087 (13) | 0.7485 (5) | 0.6188 (3) | 0.0461 (10) | |
H15A | 0.2454 | 0.7965 | 0.6491 | 0.055* | |
C16 | 0.20904 (13) | 0.6328 (5) | 0.6606 (3) | 0.0471 (10) | |
H16A | 0.2252 | 0.6029 | 0.7197 | 0.056* | |
C17 | 0.17325 (12) | 0.5619 (4) | 0.6147 (2) | 0.0380 (8) | |
H17A | 0.1648 | 0.4837 | 0.6423 | 0.046* | |
C18 | 0.14988 (11) | 0.6074 (3) | 0.5274 (2) | 0.0274 (7) | |
H18A | 0.1257 | 0.5589 | 0.4957 | 0.033* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ca1 | 0.0277 (3) | 0.0192 (3) | 0.0160 (3) | −0.0017 (3) | 0.0049 (2) | −0.0004 (2) |
O1W | 0.0300 (14) | 0.0592 (19) | 0.081 (2) | 0.0090 (13) | 0.0056 (14) | −0.0331 (17) |
O2W | 0.0325 (13) | 0.0503 (16) | 0.0402 (14) | −0.0088 (12) | 0.0099 (11) | 0.0073 (12) |
O3W | 0.039 (2) | 0.037 (2) | 0.042 (2) | 0.000 | 0.0052 (16) | 0.000 |
O4W | 0.0372 (14) | 0.0470 (16) | 0.0498 (16) | 0.0116 (12) | 0.0046 (12) | −0.0078 (13) |
O5W | 0.0536 (17) | 0.0525 (18) | 0.0481 (17) | 0.0084 (14) | 0.0024 (13) | −0.0003 (14) |
O1 | 0.0523 (15) | 0.0260 (12) | 0.0145 (10) | −0.0044 (11) | 0.0083 (10) | −0.0003 (9) |
O2 | 0.0427 (14) | 0.0231 (12) | 0.0239 (11) | −0.0063 (10) | 0.0079 (10) | −0.0014 (9) |
C1 | 0.0291 (15) | 0.0192 (14) | 0.0163 (13) | 0.0024 (12) | 0.0075 (11) | 0.0008 (11) |
C2 | 0.0311 (16) | 0.0189 (14) | 0.0124 (13) | 0.0010 (12) | 0.0054 (11) | −0.0004 (11) |
O3 | 0.0305 (14) | 0.0522 (17) | 0.0666 (19) | 0.0013 (12) | 0.0123 (13) | 0.0324 (15) |
O4 | 0.0289 (12) | 0.0279 (12) | 0.0342 (13) | 0.0022 (10) | 0.0055 (10) | 0.0104 (10) |
C3 | 0.0309 (17) | 0.0232 (15) | 0.0240 (15) | 0.0009 (13) | 0.0088 (13) | 0.0008 (13) |
C4 | 0.0285 (16) | 0.0224 (15) | 0.0212 (14) | 0.0000 (13) | 0.0033 (12) | 0.0037 (12) |
N1 | 0.0273 (13) | 0.0194 (12) | 0.0143 (11) | 0.0014 (10) | 0.0078 (9) | 0.0017 (10) |
C5 | 0.0237 (15) | 0.0260 (16) | 0.0248 (15) | 0.0038 (12) | 0.0086 (12) | 0.0038 (12) |
C6 | 0.0247 (16) | 0.0340 (18) | 0.0259 (16) | 0.0003 (14) | 0.0037 (12) | 0.0070 (14) |
C7 | 0.0348 (17) | 0.0352 (18) | 0.0192 (14) | −0.0095 (15) | 0.0032 (13) | −0.0022 (14) |
C8 | 0.0399 (18) | 0.0261 (16) | 0.0209 (15) | −0.0011 (14) | 0.0115 (13) | −0.0039 (13) |
C9 | 0.0314 (16) | 0.0222 (15) | 0.0171 (14) | 0.0027 (12) | 0.0076 (12) | 0.0015 (12) |
O5 | 0.0560 (16) | 0.0259 (12) | 0.0175 (11) | 0.0011 (11) | 0.0057 (10) | 0.0002 (9) |
O6 | 0.0531 (16) | 0.0355 (14) | 0.0291 (13) | 0.0188 (12) | 0.0043 (11) | −0.0060 (11) |
C10 | 0.0343 (17) | 0.0235 (16) | 0.0189 (14) | −0.0009 (13) | 0.0095 (12) | −0.0003 (12) |
C11 | 0.0299 (16) | 0.0217 (15) | 0.0175 (14) | 0.0012 (13) | 0.0043 (12) | 0.0012 (12) |
O7 | 0.072 (2) | 0.0411 (16) | 0.0444 (16) | 0.0118 (15) | 0.0042 (14) | −0.0240 (13) |
O8 | 0.0531 (18) | 0.0331 (15) | 0.105 (3) | 0.0117 (13) | 0.0482 (18) | −0.0001 (16) |
C12 | 0.050 (2) | 0.0243 (17) | 0.0349 (19) | 0.0073 (16) | 0.0228 (17) | 0.0079 (15) |
C13 | 0.0308 (17) | 0.0258 (16) | 0.0255 (15) | 0.0035 (13) | 0.0073 (13) | −0.0006 (13) |
C14 | 0.0351 (19) | 0.0334 (19) | 0.0343 (18) | −0.0072 (15) | 0.0068 (15) | −0.0055 (15) |
N2 | 0.0281 (13) | 0.0241 (13) | 0.0181 (12) | −0.0004 (11) | 0.0064 (10) | −0.0041 (10) |
C15 | 0.039 (2) | 0.060 (3) | 0.034 (2) | −0.0030 (19) | −0.0044 (16) | −0.0105 (19) |
C16 | 0.050 (2) | 0.061 (3) | 0.0256 (17) | 0.012 (2) | −0.0013 (16) | −0.0011 (19) |
C17 | 0.045 (2) | 0.044 (2) | 0.0264 (17) | 0.0083 (17) | 0.0102 (15) | 0.0096 (16) |
C18 | 0.0341 (17) | 0.0260 (16) | 0.0234 (15) | −0.0008 (13) | 0.0094 (13) | −0.0036 (13) |
Ca1—O1 | 2.320 (2) | C6—C7 | 1.386 (5) |
Ca1—O5 | 2.335 (2) | C6—H6A | 0.9300 |
Ca1—O7i | 2.348 (3) | C7—C8 | 1.377 (5) |
Ca1—O1W | 2.352 (3) | C7—H7A | 0.9300 |
Ca1—O4ii | 2.357 (2) | C8—C9 | 1.381 (4) |
Ca1—O2W | 2.421 (3) | C8—H8A | 0.9300 |
Ca1—C12i | 3.100 (4) | C9—H9A | 0.9300 |
O1W—H10A | 0.8890 | O5—C10 | 1.259 (4) |
O1W—H10B | 0.9814 | O6—C10 | 1.235 (4) |
O2W—H20A | 0.8066 | C10—C11 | 1.549 (4) |
O2W—H20B | 0.8721 | C11—N2 | 1.487 (4) |
O3W—H30A | 0.8990 | C11—C13 | 1.524 (4) |
O4W—H40A | 0.8738 | C11—H11A | 0.9800 |
O4W—H40B | 0.8271 | O7—C12 | 1.248 (5) |
O5W—H50A | 0.9252 | O7—Ca1ii | 2.348 (3) |
O5W—H50B | 0.9178 | O8—C12 | 1.245 (4) |
O1—C1 | 1.263 (3) | C12—C13 | 1.517 (5) |
O2—C1 | 1.240 (4) | C12—Ca1ii | 3.100 (4) |
C1—C2 | 1.551 (4) | C13—H13A | 0.9700 |
C2—N1 | 1.483 (3) | C13—H13B | 0.9700 |
C2—C4 | 1.523 (4) | C14—N2 | 1.350 (4) |
C2—H2A | 0.9800 | C14—C15 | 1.377 (5) |
O3—C3 | 1.244 (4) | C14—H14A | 0.9300 |
O4—C3 | 1.245 (4) | N2—C18 | 1.350 (4) |
O4—Ca1i | 2.357 (2) | C15—C16 | 1.376 (6) |
C3—C4 | 1.536 (4) | C15—H15A | 0.9300 |
C4—H4A | 0.9700 | C16—C17 | 1.368 (6) |
C4—H4B | 0.9700 | C16—H16A | 0.9300 |
N1—C9 | 1.343 (4) | C17—C18 | 1.373 (5) |
N1—C5 | 1.349 (4) | C17—H17A | 0.9300 |
C5—C6 | 1.358 (4) | C18—H18A | 0.9300 |
C5—H5A | 0.9300 | ||
O1—Ca1—O5 | 90.03 (8) | C6—C5—H5A | 119.5 |
O1—Ca1—O7i | 91.38 (10) | C5—C6—C7 | 119.2 (3) |
O5—Ca1—O7i | 162.23 (10) | C5—C6—H6A | 120.4 |
O1—Ca1—O1W | 97.24 (10) | C7—C6—H6A | 120.4 |
O5—Ca1—O1W | 80.08 (11) | C8—C7—C6 | 119.5 (3) |
O7i—Ca1—O1W | 82.14 (12) | C8—C7—H7A | 120.3 |
O1—Ca1—O4ii | 178.11 (9) | C6—C7—H7A | 120.3 |
O5—Ca1—O4ii | 89.36 (8) | C7—C8—C9 | 119.3 (3) |
O7i—Ca1—O4ii | 88.66 (10) | C7—C8—H8A | 120.3 |
O1W—Ca1—O4ii | 80.89 (9) | C9—C8—H8A | 120.3 |
O1—Ca1—O2W | 94.27 (9) | N1—C9—C8 | 120.1 (3) |
O5—Ca1—O2W | 80.38 (9) | N1—C9—H9A | 119.9 |
O7i—Ca1—O2W | 117.15 (10) | C8—C9—H9A | 119.9 |
O1W—Ca1—O2W | 157.27 (11) | C10—O5—Ca1 | 139.1 (2) |
O4ii—Ca1—O2W | 87.40 (9) | O6—C10—O5 | 126.0 (3) |
O1—Ca1—C12i | 88.80 (8) | O6—C10—C11 | 119.9 (3) |
O5—Ca1—C12i | 176.38 (10) | O5—C10—C11 | 114.1 (3) |
O7i—Ca1—C12i | 21.29 (10) | N2—C11—C13 | 112.3 (2) |
O1W—Ca1—C12i | 103.46 (12) | N2—C11—C10 | 110.5 (2) |
O4ii—Ca1—C12i | 91.91 (9) | C13—C11—C10 | 111.7 (3) |
O2W—Ca1—C12i | 96.29 (9) | N2—C11—H11A | 107.3 |
Ca1—O1W—H10A | 139.4 | C13—C11—H11A | 107.3 |
Ca1—O1W—H10B | 107.3 | C10—C11—H11A | 107.3 |
H10A—O1W—H10B | 113.0 | C12—O7—Ca1ii | 115.6 (2) |
Ca1—O2W—H20A | 122.8 | O8—C12—O7 | 123.1 (4) |
Ca1—O2W—H20B | 141.1 | O8—C12—C13 | 118.3 (4) |
H20A—O2W—H20B | 95.2 | O7—C12—C13 | 118.5 (3) |
H40A—O4W—H40B | 105.7 | O8—C12—Ca1ii | 80.5 (2) |
H50A—O5W—H50B | 97.9 | C13—C12—Ca1ii | 160.4 (2) |
C1—O1—Ca1 | 151.0 (2) | C12—C13—C11 | 115.2 (3) |
O2—C1—O1 | 125.8 (3) | C12—C13—H13A | 108.5 |
O2—C1—C2 | 120.3 (2) | C11—C13—H13A | 108.5 |
O1—C1—C2 | 113.9 (3) | C12—C13—H13B | 108.5 |
N1—C2—C4 | 111.3 (2) | C11—C13—H13B | 108.5 |
N1—C2—C1 | 110.9 (2) | H13A—C13—H13B | 107.5 |
C4—C2—C1 | 112.7 (2) | N2—C14—C15 | 119.9 (4) |
N1—C2—H2A | 107.2 | N2—C14—H14A | 120.1 |
C4—C2—H2A | 107.2 | C15—C14—H14A | 120.1 |
C1—C2—H2A | 107.2 | C14—N2—C18 | 120.3 (3) |
C3—O4—Ca1i | 135.4 (2) | C14—N2—C11 | 120.2 (3) |
O3—C3—O4 | 125.0 (3) | C18—N2—C11 | 119.5 (3) |
O3—C3—C4 | 117.1 (3) | C16—C15—C14 | 120.1 (4) |
O4—C3—C4 | 117.9 (3) | C16—C15—H15A | 120.0 |
C2—C4—C3 | 113.1 (2) | C14—C15—H15A | 120.0 |
C2—C4—H4A | 109.0 | C17—C16—C15 | 119.4 (4) |
C3—C4—H4A | 109.0 | C17—C16—H16A | 120.3 |
C2—C4—H4B | 109.0 | C15—C16—H16A | 120.3 |
C3—C4—H4B | 109.0 | C16—C17—C18 | 119.3 (4) |
H4A—C4—H4B | 107.8 | C16—C17—H17A | 120.3 |
C9—N1—C5 | 120.8 (3) | C18—C17—H17A | 120.3 |
C9—N1—C2 | 119.7 (2) | N2—C18—C17 | 121.0 (3) |
C5—N1—C2 | 119.5 (2) | N2—C18—H18A | 119.5 |
N1—C5—C6 | 121.0 (3) | C17—C18—H18A | 119.5 |
N1—C5—H5A | 119.5 |
Symmetry codes: (i) x, −y+2, z−1/2; (ii) x, −y+2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H10A···O4Wiii | 0.89 | 1.84 | 2.730 (4) | 179 |
O1W—H10B···O3ii | 0.98 | 1.80 | 2.715 (4) | 154 |
O2W—H20A···O3W | 0.81 | 2.14 | 2.951 (4) | 178 |
O2W—H20B···O8iv | 0.87 | 1.92 | 2.771 (4) | 166 |
O3W—H30A···O2v | 0.90 | 2.05 | 2.935 (3) | 167 |
O4W—H40A···O3 | 0.87 | 1.81 | 2.672 (4) | 170 |
O4W—H40B···O5Wvi | 0.83 | 1.99 | 2.798 (4) | 165 |
O5W—H50A···O6 | 0.93 | 1.84 | 2.761 (4) | 174 |
O5W—H50B···O4Wvii | 0.92 | 1.96 | 2.845 (4) | 162 |
Symmetry codes: (ii) x, −y+2, z+1/2; (iii) −x+1/2, −y+3/2, −z; (iv) −x, y, −z+1/2; (v) −x, −y+1, −z; (vi) −x+1/2, y+1/2, −z+1/2; (vii) x, −y+1, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Ca(C9H8NO4)2(H2O)2]·2.5H2O |
Mr | 509.48 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 294 |
a, b, c (Å) | 31.766 (14), 9.8281 (13), 14.2746 (16) |
β (°) | 103.018 (16) |
V (Å3) | 4342 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.36 |
Crystal size (mm) | 0.28 × 0.22 × 0.20 |
Data collection | |
Diffractometer | Siemens P4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.909, 0.930 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5549, 4744, 3569 |
Rint | 0.036 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.144, 1.13 |
No. of reflections | 4744 |
No. of parameters | 303 |
H-atom treatment | H-atom parameters constrained |
w = 1/[σ2(Fo2) + (0.0429P)2 + 15.5672P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.44, −0.32 |
Computer programs: XSCANS (Siemens, 1994), XSCANS, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
Ca1—O1 | 2.320 (2) | O2—C1 | 1.240 (4) |
Ca1—O5 | 2.335 (2) | O3—C3 | 1.244 (4) |
Ca1—O7i | 2.348 (3) | O4—C3 | 1.245 (4) |
Ca1—O1W | 2.352 (3) | O5—C10 | 1.259 (4) |
Ca1—O4ii | 2.357 (2) | O6—C10 | 1.235 (4) |
Ca1—O2W | 2.421 (3) | O7—C12 | 1.248 (5) |
O1—C1 | 1.263 (3) | O8—C12 | 1.245 (4) |
O1—Ca1—O5 | 90.03 (8) | O7i—Ca1—O2W | 117.15 (10) |
O1—Ca1—O7i | 91.38 (10) | O1W—Ca1—O2W | 157.27 (11) |
O5—Ca1—O7i | 162.23 (10) | O4ii—Ca1—O2W | 87.40 (9) |
O1—Ca1—O1W | 97.24 (10) | C1—O1—Ca1 | 151.0 (2) |
O5—Ca1—O1W | 80.08 (11) | O2—C1—O1 | 125.8 (3) |
O7i—Ca1—O1W | 82.14 (12) | C3—O4—Ca1i | 135.4 (2) |
O1—Ca1—O4ii | 178.11 (9) | O3—C3—O4 | 125.0 (3) |
O5—Ca1—O4ii | 89.36 (8) | O3—C3—C4 | 117.1 (3) |
O7i—Ca1—O4ii | 88.66 (10) | C10—O5—Ca1 | 139.1 (2) |
O1W—Ca1—O4ii | 80.89 (9) | O6—C10—O5 | 126.0 (3) |
O1—Ca1—O2W | 94.27 (9) | O8—C12—O7 | 123.1 (4) |
O5—Ca1—O2W | 80.38 (9) |
Symmetry codes: (i) x, −y+2, z−1/2; (ii) x, −y+2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H10A···O4Wiii | 0.89 | 1.84 | 2.730 (4) | 179 |
O1W—H10B···O3ii | 0.98 | 1.80 | 2.715 (4) | 154 |
O2W—H20A···O3W | 0.81 | 2.14 | 2.951 (4) | 178 |
O2W—H20B···O8iv | 0.87 | 1.92 | 2.771 (4) | 166 |
O3W—H30A···O2v | 0.90 | 2.05 | 2.935 (3) | 167 |
O4W—H40A···O3 | 0.87 | 1.81 | 2.672 (4) | 170 |
O4W—H40B···O5Wvi | 0.83 | 1.99 | 2.798 (4) | 165 |
O5W—H50A···O6 | 0.93 | 1.84 | 2.761 (4) | 174 |
O5W—H50B···O4Wvii | 0.92 | 1.96 | 2.845 (4) | 162 |
Symmetry codes: (ii) x, −y+2, z+1/2; (iii) −x+1/2, −y+3/2, −z; (iv) −x, y, −z+1/2; (v) −x, −y+1, −z; (vi) −x+1/2, y+1/2, −z+1/2; (vii) x, −y+1, z+1/2. |
As depicted in Fig. 1, the Ca atom in the title compound, (I), is in a distorted octahedral environment with four O atoms from the carboxylate groups of four different 2-(pyridinium-1-yl)butanedioate (L) ligands lying on the equatorial plane, and the two aqua ligands occupying the axial positions. Although the Ca—O bond lengths [2.320–2.420 (3) Å] are normal, the angles O1W—Ca1—O2W of 157.27 (11)° and O5—Ca1—O7i of 162.23 (10)° (symmetry code as in Table 1) deviate drastically from linearity. In addition, it should be noted that the carboxylate groups of L act in different coordination modes: one is in a mono-syn mode and the other in a mono-anti-skew mode with the Ca atom 0.6903 Å above the plane of the carboxylate group. With adjacent Ca atoms bridged by a pair of racemic L molecules, compound (I) displays a one-dimensional strand structure, as shown in Fig. 2.
The strands are extended into a layer by hydrogen bonds between pendent O atoms of carboxylate groups and water solvent molecules (Fig. 3). In constructing the layer, atom O3W, which is located at an inversion center, acts as hydrogen-bond donor to two pendent O atoms of two carboxylate groups from two strands [O3W···O2v = 2.936 (3) Å; symmetry code (v) as in Table 2 and −x, 1 − y, z + 1/2 Please check: Table 2 (and PLATON only give on hydrogen bond with O3W as donor] and hydrogen-bond acceptor to an aqua ligand of the third strand [O3W···O2W = 2.951 (3) Å]. Different layers are connected into a three-dimensional structure through various intermolecualar hydrogen-bond interactions between pendent O atoms [O5W···O6 = 2.762 (3) Å and O4W···O3 = 2.672 (3) Å] and aqua ligands [O4W···O1Wiii = 2.730 (3) Å].