Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807052439/ng2347sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807052439/ng2347Isup2.hkl |
CCDC reference: 667231
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.006 Å
- R factor = 0.041
- wR factor = 0.098
- Data-to-parameter ratio = 16.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT128_ALERT_4_C Non-standard setting of Space group P2/c .... P2/n PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cd1 - O1 .. 7.77 su PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2 PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.14 Ratio
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C34 H34 Cd1 Cl2 N4 O8 Atom count from _chemical_formula_moiety:C34 H34 Cd1 Cl1 N4 O8 PLAT794_ALERT_5_G Check Predicted Bond Valency for Cd1 (2) 2.03 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 3 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
For the cadmium complexes with imidazole, benzimidazole and phenanthroline donor-ligands, see Deng et al. (2006a,b, 2007).
Cadmium(II) diacetate dihydrate (2.66 g, 10 mmol) was added to an H2O/EtOH solution (1:1 v/v) of 4-formylbenzoic acid (3.00 g, 20 mmol) and N,N'-(1,3-phenylenebis(methylene))dipyridin-2-amine (2.92 g 10 mmol). Sodium hydroxide (0.1 M) was added dropwise until the pH value being 6. Colorless single crystals separated from the filtered solution after several days. CH&N analysis. Calc. for C34H34N4O8Cl2Cd: C 50.42, H 4.23, N 6.92. Found: C 50.45, H 4.24, N 6.91.
Carbon- and nitrogen bound H atoms were placed in calculated positions, with C—H = 0.93, N—H = 0.86 and Uiso(H) = 1.2Ueq (C,N), and were included in the refinement in the riding model approximation. The H atoms of water molecules were located in difference Fourier maps and refined with the O—H and H···H distance restraints to 0.85 (1) and 1.39 (1) Å, and with Uiso(H) = 1.5Ueq(O).
Cadmium bis(4-formylbenzoate) forms a hydrated 1:2 adduct with imidazole (Deng et al., 2006a), two 1:1 aqua adducts with the larger benzimidazole ligand (Deng et al., 2006b) as well as an adduct with 1,10-phenanthroline (Deng et al., 2007). Replacing the these N-heterocycles by N,N'-(1,3-phenylenebis(methylene))dipyridin-2-amine furnishes the title compound as a salt whose anion has two 4-formylbenzoate ligands binding to the dichlorocadmium group; the N-heterocycle itself is displaced from the coordination sphere as it exists as a protonated cation (Fig.1). Hydrogen bonds link the cation, anion and lattice water into a chain structure along the a axis (Fig. 2).
For the cadmium complexes with imidazole, benzimidazole and phenanthroline donor-ligands, see Deng et al. (2006a,b, 2007).
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); 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 (Sheldrick, 1997).
(C18H20N4)[CdCl2(C8H5O3)2]·2H2O | F(000) = 824 |
Mr = 809.95 | Dx = 1.567 Mg m−3 |
Monoclinic, P2/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yac | Cell parameters from 10612 reflections |
a = 7.7856 (16) Å | θ = 3.1–27.5° |
b = 11.956 (2) Å | µ = 0.85 mm−1 |
c = 18.509 (4) Å | T = 295 K |
β = 94.84 (3)° | Prism, colorless |
V = 1716.8 (6) Å3 | 0.36 × 0.29 × 0.18 mm |
Z = 2 |
Rigaku R-AXIS RAPID diffractometer | 3918 independent reflections |
Radiation source: fine-focus sealed tube | 2592 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.057 |
Detector resolution: 10.000 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −10→9 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −15→15 |
Tmin = 0.750, Tmax = 0.862 | l = −23→23 |
16167 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) = 0.098 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + 4.8999P] where P = (Fo2 + 2Fc2)/3 |
3918 reflections | (Δ/σ)max < 0.001 |
235 parameters | Δρmax = 1.18 e Å−3 |
5 restraints | Δρmin = −1.51 e Å−3 |
(C18H20N4)[CdCl2(C8H5O3)2]·2H2O | V = 1716.8 (6) Å3 |
Mr = 809.95 | Z = 2 |
Monoclinic, P2/n | Mo Kα radiation |
a = 7.7856 (16) Å | µ = 0.85 mm−1 |
b = 11.956 (2) Å | T = 295 K |
c = 18.509 (4) Å | 0.36 × 0.29 × 0.18 mm |
β = 94.84 (3)° |
Rigaku R-AXIS RAPID diffractometer | 3918 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 2592 reflections with I > 2σ(I) |
Tmin = 0.750, Tmax = 0.862 | Rint = 0.057 |
16167 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 5 restraints |
wR(F2) = 0.098 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | Δρmax = 1.18 e Å−3 |
3918 reflections | Δρmin = −1.51 e Å−3 |
235 parameters |
x | y | z | Uiso*/Ueq | ||
Cd1 | 0.7500 | 0.53198 (4) | 0.2500 | 0.03870 (14) | |
Cl1 | 0.49551 (16) | 0.65424 (11) | 0.25523 (7) | 0.0566 (3) | |
O1W | 0.3005 (5) | 0.4707 (4) | 0.3449 (2) | 0.0804 (12) | |
H1W1 | 0.337 (7) | 0.526 (4) | 0.321 (3) | 0.121* | |
H1W2 | 0.201 (4) | 0.452 (5) | 0.327 (3) | 0.121* | |
O1 | 0.9408 (4) | 0.3811 (3) | 0.30373 (16) | 0.0529 (8) | |
O2 | 0.7587 (4) | 0.4687 (3) | 0.36951 (16) | 0.0486 (8) | |
O3 | 1.1884 (5) | 0.0472 (3) | 0.6110 (2) | 0.0783 (12) | |
N1 | 0.4510 (5) | 0.3320 (3) | 0.4498 (3) | 0.0532 (10) | |
H1N | 0.409 (6) | 0.386 (3) | 0.423 (2) | 0.064* | |
N2 | 0.5264 (5) | 0.2507 (3) | 0.3447 (2) | 0.0486 (10) | |
H2N | 0.495 (6) | 0.312 (2) | 0.323 (2) | 0.058* | |
C1 | 0.8746 (6) | 0.3968 (4) | 0.3627 (2) | 0.0403 (10) | |
C2 | 0.9362 (5) | 0.3271 (3) | 0.4277 (2) | 0.0357 (9) | |
C3 | 0.9058 (6) | 0.3627 (4) | 0.4967 (2) | 0.0431 (11) | |
H3 | 0.8470 | 0.4293 | 0.5030 | 0.052* | |
C4 | 0.9632 (6) | 0.2992 (4) | 0.5562 (2) | 0.0457 (11) | |
H4 | 0.9448 | 0.3241 | 0.6026 | 0.055* | |
C5 | 1.0478 (5) | 0.1988 (4) | 0.5477 (2) | 0.0427 (11) | |
C6 | 1.0754 (6) | 0.1623 (4) | 0.4780 (2) | 0.0466 (11) | |
H6 | 1.1304 | 0.0944 | 0.4715 | 0.056* | |
C7 | 1.0212 (6) | 0.2268 (4) | 0.4191 (2) | 0.0447 (11) | |
H7 | 1.0419 | 0.2028 | 0.3728 | 0.054* | |
C8 | 1.1105 (7) | 0.1334 (4) | 0.6124 (3) | 0.0597 (14) | |
H8 | 1.0878 | 0.1613 | 0.6575 | 0.072* | |
C9 | 0.4429 (7) | 0.3363 (5) | 0.5225 (3) | 0.0658 (15) | |
H9 | 0.3978 | 0.3994 | 0.5434 | 0.079* | |
C10 | 0.4993 (7) | 0.2502 (5) | 0.5646 (3) | 0.0691 (16) | |
H10 | 0.4947 | 0.2528 | 0.6146 | 0.083* | |
C11 | 0.5647 (7) | 0.1570 (5) | 0.5314 (3) | 0.0615 (14) | |
H11 | 0.6045 | 0.0967 | 0.5598 | 0.074* | |
C12 | 0.5720 (6) | 0.1522 (4) | 0.4585 (2) | 0.0466 (11) | |
H12 | 0.6138 | 0.0885 | 0.4371 | 0.056* | |
C13 | 0.5161 (5) | 0.2434 (4) | 0.4161 (2) | 0.0421 (11) | |
C14 | 0.5600 (5) | 0.1570 (4) | 0.2978 (2) | 0.0440 (11) | |
H14A | 0.6432 | 0.1074 | 0.3233 | 0.053* | |
H14B | 0.6106 | 0.1849 | 0.2552 | 0.053* | |
C15 | 0.3994 (5) | 0.0913 (4) | 0.2741 (2) | 0.0342 (9) | |
C16 | 0.3974 (6) | −0.0243 (4) | 0.2739 (2) | 0.0499 (11) | |
H16 | 0.4962 | −0.0637 | 0.2899 | 0.060* | |
C17 | 0.2500 | −0.0812 (6) | 0.2500 | 0.064 (2) | |
H17 | 0.2500 | −0.1590 | 0.2500 | 0.076* | |
C18 | 0.2500 | 0.1479 (5) | 0.2500 | 0.0358 (13) | |
H18 | 0.2500 | 0.2257 | 0.2500 | 0.043* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cd1 | 0.0447 (3) | 0.0372 (3) | 0.0335 (2) | 0.000 | −0.00057 (18) | 0.000 |
Cl1 | 0.0639 (8) | 0.0584 (8) | 0.0477 (7) | 0.0228 (6) | 0.0067 (6) | 0.0049 (6) |
O1W | 0.061 (2) | 0.087 (3) | 0.091 (3) | 0.001 (2) | −0.007 (2) | 0.033 (3) |
O1 | 0.066 (2) | 0.058 (2) | 0.0358 (18) | 0.0016 (17) | 0.0064 (15) | 0.0077 (16) |
O2 | 0.0547 (19) | 0.0426 (18) | 0.0472 (18) | 0.0057 (16) | −0.0026 (14) | 0.0094 (16) |
O3 | 0.100 (3) | 0.062 (3) | 0.070 (3) | 0.033 (2) | −0.007 (2) | 0.013 (2) |
N1 | 0.048 (2) | 0.043 (3) | 0.067 (3) | −0.0032 (19) | −0.001 (2) | −0.004 (2) |
N2 | 0.053 (2) | 0.040 (2) | 0.050 (2) | −0.0052 (19) | −0.0097 (19) | 0.0072 (19) |
C1 | 0.043 (3) | 0.034 (2) | 0.042 (3) | −0.007 (2) | −0.004 (2) | 0.001 (2) |
C2 | 0.034 (2) | 0.036 (2) | 0.036 (2) | −0.0032 (18) | −0.0009 (17) | 0.0023 (19) |
C3 | 0.048 (3) | 0.038 (2) | 0.042 (3) | 0.005 (2) | −0.002 (2) | −0.001 (2) |
C4 | 0.054 (3) | 0.047 (3) | 0.036 (2) | 0.005 (2) | 0.000 (2) | −0.004 (2) |
C5 | 0.043 (3) | 0.041 (3) | 0.042 (3) | 0.002 (2) | −0.003 (2) | 0.006 (2) |
C6 | 0.053 (3) | 0.043 (3) | 0.044 (3) | 0.011 (2) | 0.002 (2) | 0.000 (2) |
C7 | 0.048 (3) | 0.049 (3) | 0.036 (2) | 0.006 (2) | 0.003 (2) | −0.003 (2) |
C8 | 0.074 (4) | 0.057 (3) | 0.047 (3) | 0.010 (3) | 0.000 (3) | 0.009 (3) |
C9 | 0.057 (3) | 0.058 (4) | 0.084 (4) | −0.011 (3) | 0.016 (3) | −0.023 (3) |
C10 | 0.076 (4) | 0.085 (5) | 0.049 (3) | −0.021 (3) | 0.016 (3) | −0.016 (3) |
C11 | 0.072 (4) | 0.062 (4) | 0.050 (3) | −0.007 (3) | 0.004 (3) | 0.006 (3) |
C12 | 0.056 (3) | 0.043 (3) | 0.042 (3) | −0.002 (2) | 0.008 (2) | 0.002 (2) |
C13 | 0.037 (2) | 0.043 (3) | 0.045 (3) | −0.011 (2) | −0.002 (2) | −0.004 (2) |
C14 | 0.037 (2) | 0.057 (3) | 0.038 (2) | −0.002 (2) | 0.0004 (19) | 0.008 (2) |
C15 | 0.036 (2) | 0.041 (2) | 0.027 (2) | 0.0027 (19) | 0.0061 (16) | 0.0030 (19) |
C16 | 0.053 (3) | 0.043 (3) | 0.053 (3) | 0.009 (2) | −0.001 (2) | 0.003 (2) |
C17 | 0.072 (5) | 0.035 (4) | 0.081 (6) | 0.000 | −0.009 (4) | 0.000 |
C18 | 0.042 (3) | 0.033 (3) | 0.032 (3) | 0.000 | 0.004 (3) | 0.000 |
Cd1—O2i | 2.333 (3) | C5—C6 | 1.396 (6) |
Cd1—O2 | 2.333 (3) | C5—C8 | 1.477 (6) |
Cd1—Cl1i | 2.4707 (12) | C6—C7 | 1.372 (6) |
Cd1—Cl1 | 2.4707 (12) | C6—H6 | 0.9300 |
Cd1—O1i | 2.490 (3) | C7—H7 | 0.9300 |
Cd1—O1 | 2.490 (3) | C8—H8 | 0.9300 |
Cd1—C1i | 2.750 (4) | C9—C10 | 1.342 (8) |
Cd1—C1 | 2.750 (4) | C9—H9 | 0.9300 |
O1W—H1W1 | 0.86 (5) | C10—C11 | 1.390 (7) |
O1W—H1W2 | 0.86 (5) | C10—H10 | 0.9300 |
O1—C1 | 1.260 (5) | C11—C12 | 1.357 (6) |
O2—C1 | 1.260 (5) | C11—H11 | 0.9300 |
O3—C8 | 1.197 (6) | C12—C13 | 1.392 (6) |
N1—C13 | 1.350 (6) | C12—H12 | 0.9300 |
N1—C9 | 1.353 (7) | C14—C15 | 1.510 (6) |
N1—H1N | 0.86 (4) | C14—H14A | 0.9700 |
N2—C13 | 1.332 (6) | C14—H14B | 0.9700 |
N2—C14 | 1.455 (6) | C15—C16 | 1.382 (6) |
N2—H2N | 0.86 (3) | C15—C18 | 1.386 (5) |
C1—C2 | 1.508 (6) | C16—C17 | 1.375 (6) |
C2—C7 | 1.385 (6) | C16—H16 | 0.9300 |
C2—C3 | 1.387 (6) | C17—C16ii | 1.375 (6) |
C3—C4 | 1.381 (6) | C17—H17 | 0.9300 |
C3—H3 | 0.9300 | C18—C15ii | 1.386 (5) |
C4—C5 | 1.384 (6) | C18—H18 | 0.9300 |
C4—H4 | 0.9300 | ||
O2i—Cd1—O2 | 142.15 (16) | C3—C4—C5 | 120.8 (4) |
O2i—Cd1—Cl1i | 96.55 (8) | C3—C4—H4 | 119.6 |
O2—Cd1—Cl1i | 105.65 (8) | C5—C4—H4 | 119.6 |
O2i—Cd1—Cl1 | 105.65 (8) | C4—C5—C6 | 119.2 (4) |
O2—Cd1—Cl1 | 96.55 (8) | C4—C5—C8 | 119.6 (4) |
Cl1i—Cd1—Cl1 | 107.45 (7) | C6—C5—C8 | 121.1 (4) |
O2i—Cd1—O1i | 54.40 (10) | C7—C6—C5 | 119.8 (4) |
O2—Cd1—O1i | 96.45 (11) | C7—C6—H6 | 120.1 |
Cl1i—Cd1—O1i | 150.04 (8) | C5—C6—H6 | 120.1 |
Cl1—Cd1—O1i | 89.47 (8) | C6—C7—C2 | 120.9 (4) |
O2i—Cd1—O1 | 96.45 (11) | C6—C7—H7 | 119.5 |
O2—Cd1—O1 | 54.40 (10) | C2—C7—H7 | 119.5 |
Cl1i—Cd1—O1 | 89.47 (8) | O3—C8—C5 | 124.9 (5) |
Cl1—Cd1—O1 | 150.04 (8) | O3—C8—H8 | 117.6 |
O1i—Cd1—O1 | 87.16 (15) | C5—C8—H8 | 117.6 |
O2i—Cd1—C1i | 27.16 (12) | C10—C9—N1 | 120.5 (5) |
O2—Cd1—C1i | 120.56 (13) | C10—C9—H9 | 119.7 |
Cl1i—Cd1—C1i | 123.42 (10) | N1—C9—H9 | 119.7 |
Cl1—Cd1—C1i | 98.32 (9) | C9—C10—C11 | 118.2 (5) |
O1i—Cd1—C1i | 27.24 (11) | C9—C10—H10 | 120.9 |
O1—Cd1—C1i | 92.15 (11) | C11—C10—H10 | 120.9 |
O2i—Cd1—C1 | 120.56 (13) | C12—C11—C10 | 121.4 (5) |
O2—Cd1—C1 | 27.16 (11) | C12—C11—H11 | 119.3 |
Cl1i—Cd1—C1 | 98.32 (9) | C10—C11—H11 | 119.3 |
Cl1—Cd1—C1 | 123.42 (10) | C11—C12—C13 | 119.4 (5) |
O1i—Cd1—C1 | 92.15 (11) | C11—C12—H12 | 120.3 |
O1—Cd1—C1 | 27.24 (11) | C13—C12—H12 | 120.3 |
C1i—Cd1—C1 | 108.00 (18) | N2—C13—N1 | 117.6 (4) |
H1W1—O1W—H1W2 | 110 (5) | N2—C13—C12 | 124.6 (4) |
C1—O1—Cd1 | 87.9 (3) | N1—C13—C12 | 117.7 (4) |
C1—O2—Cd1 | 95.2 (3) | N2—C14—C15 | 112.8 (3) |
C13—N1—C9 | 122.8 (5) | N2—C14—H14A | 109.0 |
C13—N1—H1N | 117 (3) | C15—C14—H14A | 109.0 |
C9—N1—H1N | 120 (4) | N2—C14—H14B | 109.0 |
C13—N2—C14 | 124.8 (4) | C15—C14—H14B | 109.0 |
C13—N2—H2N | 119 (3) | H14A—C14—H14B | 107.8 |
C14—N2—H2N | 115 (3) | C16—C15—C18 | 118.6 (4) |
O1—C1—O2 | 122.5 (4) | C16—C15—C14 | 122.0 (4) |
O1—C1—C2 | 118.9 (4) | C18—C15—C14 | 119.4 (4) |
O2—C1—C2 | 118.6 (4) | C17—C16—C15 | 120.3 (5) |
O1—C1—Cd1 | 64.8 (2) | C17—C16—H16 | 119.8 |
O2—C1—Cd1 | 57.7 (2) | C15—C16—H16 | 119.8 |
C2—C1—Cd1 | 176.3 (3) | C16—C17—C16ii | 120.6 (7) |
C7—C2—C3 | 119.4 (4) | C16—C17—H17 | 119.7 |
C7—C2—C1 | 120.7 (4) | C16ii—C17—H17 | 119.7 |
C3—C2—C1 | 119.9 (4) | C15ii—C18—C15 | 121.6 (6) |
C4—C3—C2 | 119.8 (4) | C15ii—C18—H18 | 119.2 |
C4—C3—H3 | 120.1 | C15—C18—H18 | 119.2 |
C2—C3—H3 | 120.1 | ||
O2i—Cd1—O1—C1 | −154.0 (2) | O2—C1—C2—C3 | −19.0 (6) |
O2—Cd1—O1—C1 | −0.3 (2) | C7—C2—C3—C4 | 1.2 (6) |
Cl1i—Cd1—O1—C1 | 109.5 (2) | C1—C2—C3—C4 | −179.6 (4) |
Cl1—Cd1—O1—C1 | −16.3 (3) | C2—C3—C4—C5 | −1.4 (7) |
O1i—Cd1—O1—C1 | −100.3 (3) | C3—C4—C5—C6 | 0.3 (7) |
C1i—Cd1—O1—C1 | −127.1 (2) | C3—C4—C5—C8 | 178.9 (4) |
O2i—Cd1—O2—C1 | 46.1 (2) | C4—C5—C6—C7 | 1.0 (7) |
Cl1i—Cd1—O2—C1 | −77.5 (3) | C8—C5—C6—C7 | −177.6 (4) |
Cl1—Cd1—O2—C1 | 172.3 (2) | C5—C6—C7—C2 | −1.2 (7) |
O1i—Cd1—O2—C1 | 82.1 (3) | C3—C2—C7—C6 | 0.1 (7) |
O1—Cd1—O2—C1 | 0.3 (2) | C1—C2—C7—C6 | −179.1 (4) |
C1i—Cd1—O2—C1 | 68.6 (3) | C4—C5—C8—O3 | −178.1 (5) |
Cd1—O1—C1—O2 | 0.5 (4) | C6—C5—C8—O3 | 0.5 (8) |
Cd1—O1—C1—C2 | −179.5 (3) | C13—N1—C9—C10 | −0.6 (8) |
Cd1—O2—C1—O1 | −0.5 (4) | N1—C9—C10—C11 | −0.4 (8) |
Cd1—O2—C1—C2 | 179.4 (3) | C9—C10—C11—C12 | −0.1 (8) |
O2i—Cd1—C1—O1 | 30.4 (3) | C10—C11—C12—C13 | 1.4 (8) |
O2—Cd1—C1—O1 | 179.5 (4) | C14—N2—C13—N1 | −167.1 (4) |
Cl1i—Cd1—C1—O1 | −72.3 (2) | C14—N2—C13—C12 | 14.7 (7) |
Cl1—Cd1—C1—O1 | 170.4 (2) | C9—N1—C13—N2 | −176.4 (4) |
O1i—Cd1—C1—O1 | 79.6 (3) | C9—N1—C13—C12 | 1.9 (7) |
C1i—Cd1—C1—O1 | 57.0 (2) | C11—C12—C13—N2 | 175.9 (4) |
O2i—Cd1—C1—O2 | −149.1 (2) | C11—C12—C13—N1 | −2.3 (7) |
Cl1i—Cd1—C1—O2 | 108.2 (2) | C13—N2—C14—C15 | 83.6 (5) |
Cl1—Cd1—C1—O2 | −9.2 (3) | N2—C14—C15—C16 | −136.2 (4) |
O1i—Cd1—C1—O2 | −100.0 (2) | N2—C14—C15—C18 | 45.5 (5) |
O1—Cd1—C1—O2 | −179.5 (4) | C18—C15—C16—C17 | 0.2 (6) |
C1i—Cd1—C1—O2 | −122.5 (3) | C14—C15—C16—C17 | −178.2 (3) |
O1—C1—C2—C7 | −19.8 (6) | C15—C16—C17—C16ii | −0.1 (3) |
O2—C1—C2—C7 | 160.3 (4) | C16—C15—C18—C15ii | −0.1 (3) |
O1—C1—C2—C3 | 161.0 (4) | C14—C15—C18—C15ii | 178.3 (4) |
Symmetry codes: (i) −x+3/2, y, −z+1/2; (ii) −x+1/2, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···Cl1 | 0.86 (5) | 2.37 (5) | 3.209 (4) | 167 (6) |
O1W—H1W2···O1iii | 0.86 (5) | 2.21 (4) | 3.035 (5) | 167 (5) |
N1—H1N···O1W | 0.86 (4) | 1.90 (4) | 2.741 (6) | 164 (5) |
N2—H2N···O1W | 0.86 (3) | 2.49 (3) | 3.164 (6) | 136 (4) |
N2—H2N···O1i | 0.86 (3) | 2.57 (4) | 3.188 (5) | 129 (4) |
Symmetry codes: (i) −x+3/2, y, −z+1/2; (iii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | (C18H20N4)[CdCl2(C8H5O3)2]·2H2O |
Mr | 809.95 |
Crystal system, space group | Monoclinic, P2/n |
Temperature (K) | 295 |
a, b, c (Å) | 7.7856 (16), 11.956 (2), 18.509 (4) |
β (°) | 94.84 (3) |
V (Å3) | 1716.8 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.85 |
Crystal size (mm) | 0.36 × 0.29 × 0.18 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.750, 0.862 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16167, 3918, 2592 |
Rint | 0.057 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.098, 1.10 |
No. of reflections | 3918 |
No. of parameters | 235 |
No. of restraints | 5 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.18, −1.51 |
Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976).
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···Cl1 | 0.86 (5) | 2.37 (5) | 3.209 (4) | 167 (6) |
O1W—H1W2···O1i | 0.86 (5) | 2.21 (4) | 3.035 (5) | 167 (5) |
N1—H1N···O1W | 0.86 (4) | 1.90 (4) | 2.741 (6) | 164 (5) |
N2—H2N···O1W | 0.86 (3) | 2.49 (3) | 3.164 (6) | 136 (4) |
N2—H2N···O1ii | 0.86 (3) | 2.57 (4) | 3.188 (5) | 129 (4) |
Symmetry codes: (i) x−1, y, z; (ii) −x+3/2, y, −z+1/2. |
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Cadmium bis(4-formylbenzoate) forms a hydrated 1:2 adduct with imidazole (Deng et al., 2006a), two 1:1 aqua adducts with the larger benzimidazole ligand (Deng et al., 2006b) as well as an adduct with 1,10-phenanthroline (Deng et al., 2007). Replacing the these N-heterocycles by N,N'-(1,3-phenylenebis(methylene))dipyridin-2-amine furnishes the title compound as a salt whose anion has two 4-formylbenzoate ligands binding to the dichlorocadmium group; the N-heterocycle itself is displaced from the coordination sphere as it exists as a protonated cation (Fig.1). Hydrogen bonds link the cation, anion and lattice water into a chain structure along the a axis (Fig. 2).