Compared with the monomorphic type of ligand, combining mixed ligands in one coordination polymer offers greater tunability of the structural framework. Employment of N-heterocyclic ligands and aromatic polycarboxylates is an effective approach for the construction of metal–organic frameworks (MOFs). Two new coordination polymers incorporating both 2-[(1H-imidazol-1-yl)methyl]-1H-benzimidazole (imb) and benzenedicarboxylic acid isomers, namely, catena-poly[[[di-μ-chlorido-bis[(2-carboxybenzoato-κ2O1,O1′)cadmium(II)]]-bis{μ-2-[(1H-imidazol-1-yl)methyl]-1H-benzimidazole-κ2N:N′}] dihydrate], {[Cd(C8H5O4)Cl(C11H10N4)]·H2O}n, (I), and poly[[aqua(μ2-benzene-1,3-dicarboxylato-κ3O1,O1′:O3){μ2-2-[(1H-imidazol-1-yl)methyl]-1H-benzimidazole-κ2N:N′}cadmium(II)] dihydrate], {[Cd(C8H4O4)(C11H10N4)(H2O)]·2H2O}n, (II), have been prepared and structurally characterized by single-crystal X-ray diffraction. In polymer (I), imb ligands bridge CdII ions, forming a one-dimensional chain, and 2-carboxybenzoate anions coordinate to the CdII ions in a terminal fashion. Polymer (II) exhibits a two-dimensional network structure in which imb ligands and the benzene-1,3-dicarboxylate anions join CdII ions co-operatively. This indicates that changing of the aromatic dicarboxylic acids can result in polymers with different compositions and architectures. Moreover, their IR spectra, PXRD (powder X-ray diffraction) patterns, thermogravimetric analyses and fluorescence properties were also investigated.
Supporting information
CCDC references: 1036799; 1036798
For both structures, data collection: CrystalClear (Rigaku/MSC, 2004); cell refinement: CrystalClear (Rigaku/MSC, 2004); data reduction: CrystalClear (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: publCIF (Westrip, 2010).
catena-Poly[[[di-µ-chlorido-bis[(2-carboxybenzoato-
κ2O1,
O1')cadmium(II)]]-bis{µ-2-[(1
H-imidazol-1-yl)methyl]-1
H-benzimidazole-
κ2N:
N'}] dihydrate] (I)
top
Crystal data top
[Cd(C8H5O4)Cl(C11H10N4)]·H2O | Z = 2 |
Mr = 529.21 | F(000) = 528 |
Triclinic, P1 | Dx = 1.783 Mg m−3 |
a = 8.5888 (17) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.372 (2) Å | Cell parameters from 3326 reflections |
c = 11.660 (2) Å | θ = 2.0–27.9° |
α = 64.87 (3)° | µ = 1.28 mm−1 |
β = 73.10 (3)° | T = 293 K |
γ = 80.71 (3)° | Prism, colourless |
V = 985.6 (4) Å3 | 0.19 × 0.18 × 0.16 mm |
Data collection top
Rigaku Saturn diffractometer | 4646 independent reflections |
Radiation source: fine-focus sealed tube | 4153 reflections with I > 2σ(I) |
Detector resolution: 28.5714 pixels mm-1 | Rint = 0.026 |
ω scans | θmax = 27.9°, θmin = 2.0° |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004) | h = −11→11 |
Tmin = 0.925, Tmax = 1.000 | k = −14→14 |
9602 measured reflections | l = −15→15 |
Refinement top
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)] = 0.038 | Hydrogen site location: mixed |
wR(F2) = 0.075 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0257P)2 + 0.7865P] where P = (Fo2 + 2Fc2)/3 |
4646 reflections | (Δ/σ)max = 0.001 |
262 parameters | Δρmax = 0.57 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cd1 | 0.34122 (3) | 0.14547 (2) | 0.48348 (2) | 0.03004 (8) | |
Cl1 | 0.54477 (10) | 0.00851 (8) | 0.63219 (8) | 0.03943 (19) | |
O1 | 0.1237 (3) | 0.0356 (2) | 0.6555 (2) | 0.0474 (6) | |
O2 | 0.1733 (3) | 0.2101 (2) | 0.6645 (2) | 0.0482 (6) | |
O3 | 0.0762 (3) | 0.3390 (2) | 0.7952 (3) | 0.0565 (7) | |
H3A | 0.1084 | 0.2966 | 0.7502 | 0.085* | |
O4 | −0.1104 (4) | 0.3310 (3) | 0.9692 (3) | 0.0777 (10) | |
N1 | 0.1430 (3) | 0.2317 (3) | 0.3688 (3) | 0.0360 (6) | |
N2 | −0.0788 (3) | 0.2614 (2) | 0.3014 (3) | 0.0318 (6) | |
N3 | 0.4796 (3) | 0.3310 (2) | 0.3800 (2) | 0.0277 (5) | |
N4 | 0.6742 (3) | 0.4721 (2) | 0.2934 (3) | 0.0344 (6) | |
H4A | 0.7699 | 0.5026 | 0.2584 | 0.041* | |
C1 | 0.0945 (3) | 0.1115 (3) | 0.7061 (3) | 0.0293 (6) | |
C2 | −0.0521 (4) | 0.0855 (3) | 0.8279 (3) | 0.0340 (7) | |
C3 | −0.1337 (4) | −0.0267 (3) | 0.8619 (4) | 0.0444 (8) | |
H3 | −0.0965 | −0.0755 | 0.8116 | 0.053* | |
C4 | −0.2654 (4) | −0.0666 (4) | 0.9661 (4) | 0.0517 (9) | |
H4 | −0.3173 | −0.1409 | 0.9855 | 0.062* | |
C5 | −0.3208 (5) | 0.0036 (4) | 1.0423 (4) | 0.0535 (10) | |
H5 | −0.4093 | −0.0240 | 1.1144 | 0.064* | |
C6 | −0.2458 (4) | 0.1143 (4) | 1.0121 (4) | 0.0470 (9) | |
H6 | −0.2855 | 0.1615 | 1.0639 | 0.056* | |
C7 | −0.1106 (4) | 0.1586 (3) | 0.9051 (3) | 0.0371 (7) | |
C8 | −0.0461 (5) | 0.2836 (4) | 0.8905 (4) | 0.0465 (8) | |
C9 | −0.0078 (3) | 0.1976 (3) | 0.4000 (3) | 0.0317 (7) | |
H9 | −0.0586 | 0.1364 | 0.4808 | 0.038* | |
C10 | 0.1686 (4) | 0.3217 (4) | 0.2434 (4) | 0.0541 (10) | |
H10 | 0.2654 | 0.3636 | 0.1946 | 0.065* | |
C11 | 0.0338 (4) | 0.3416 (4) | 0.2002 (4) | 0.0504 (9) | |
H11 | 0.0199 | 0.3983 | 0.1180 | 0.061* | |
C12 | −0.2443 (3) | 0.2474 (3) | 0.3006 (3) | 0.0358 (7) | |
H12A | −0.2804 | 0.1626 | 0.3658 | 0.043* | |
H12B | −0.2431 | 0.2507 | 0.2158 | 0.043* | |
C13 | 0.6363 (3) | 0.3491 (3) | 0.3275 (3) | 0.0292 (6) | |
C14 | 0.5314 (4) | 0.5404 (3) | 0.3248 (3) | 0.0310 (6) | |
C15 | 0.4999 (4) | 0.6688 (3) | 0.3110 (4) | 0.0405 (8) | |
H15 | 0.5827 | 0.7271 | 0.2756 | 0.049* | |
C16 | 0.3404 (4) | 0.7053 (3) | 0.3520 (4) | 0.0437 (8) | |
H16 | 0.3144 | 0.7903 | 0.3449 | 0.052* | |
C17 | 0.2164 (4) | 0.6180 (3) | 0.4042 (4) | 0.0431 (8) | |
H17 | 0.1093 | 0.6465 | 0.4296 | 0.052* | |
C18 | 0.2488 (4) | 0.4904 (3) | 0.4190 (3) | 0.0389 (8) | |
H18 | 0.1659 | 0.4322 | 0.4550 | 0.047* | |
C19 | 0.4101 (3) | 0.4518 (3) | 0.3780 (3) | 0.0295 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cd1 | 0.02381 (11) | 0.02566 (12) | 0.03979 (14) | −0.00180 (8) | −0.00474 (9) | −0.01410 (10) |
Cl1 | 0.0453 (4) | 0.0392 (4) | 0.0426 (5) | 0.0095 (3) | −0.0175 (4) | −0.0243 (4) |
O1 | 0.0409 (13) | 0.0453 (14) | 0.0495 (15) | −0.0054 (11) | 0.0018 (11) | −0.0201 (12) |
O2 | 0.0377 (13) | 0.0488 (14) | 0.0527 (16) | −0.0094 (11) | 0.0022 (11) | −0.0215 (12) |
O3 | 0.0519 (16) | 0.0534 (15) | 0.0672 (18) | −0.0220 (12) | 0.0070 (14) | −0.0342 (14) |
O4 | 0.104 (3) | 0.072 (2) | 0.068 (2) | −0.0217 (18) | 0.0062 (18) | −0.0491 (18) |
N1 | 0.0253 (13) | 0.0406 (15) | 0.0434 (16) | −0.0021 (11) | −0.0081 (12) | −0.0179 (13) |
N2 | 0.0225 (12) | 0.0301 (13) | 0.0448 (16) | 0.0008 (10) | −0.0074 (11) | −0.0181 (12) |
N3 | 0.0239 (12) | 0.0211 (11) | 0.0376 (14) | −0.0023 (9) | −0.0095 (10) | −0.0095 (11) |
N4 | 0.0241 (12) | 0.0281 (13) | 0.0499 (17) | −0.0054 (10) | −0.0081 (12) | −0.0139 (12) |
C1 | 0.0259 (14) | 0.0237 (14) | 0.0370 (17) | 0.0023 (11) | −0.0127 (13) | −0.0089 (13) |
C2 | 0.0312 (16) | 0.0343 (16) | 0.0345 (17) | 0.0015 (13) | −0.0094 (13) | −0.0121 (14) |
C3 | 0.0403 (19) | 0.0439 (19) | 0.049 (2) | −0.0070 (15) | −0.0063 (16) | −0.0203 (17) |
C4 | 0.046 (2) | 0.048 (2) | 0.055 (2) | −0.0165 (17) | −0.0026 (18) | −0.0152 (19) |
C5 | 0.042 (2) | 0.063 (2) | 0.045 (2) | −0.0168 (18) | 0.0016 (17) | −0.015 (2) |
C6 | 0.045 (2) | 0.056 (2) | 0.040 (2) | −0.0031 (17) | −0.0061 (16) | −0.0220 (18) |
C7 | 0.0342 (17) | 0.0421 (18) | 0.0356 (18) | −0.0022 (14) | −0.0110 (14) | −0.0143 (15) |
C8 | 0.047 (2) | 0.048 (2) | 0.050 (2) | −0.0026 (17) | −0.0127 (18) | −0.0247 (18) |
C9 | 0.0250 (14) | 0.0271 (14) | 0.0404 (18) | −0.0017 (11) | −0.0066 (13) | −0.0118 (13) |
C10 | 0.0305 (17) | 0.061 (2) | 0.055 (2) | −0.0147 (16) | −0.0066 (16) | −0.008 (2) |
C11 | 0.0368 (19) | 0.054 (2) | 0.045 (2) | −0.0106 (16) | −0.0113 (16) | −0.0013 (18) |
C12 | 0.0251 (15) | 0.0356 (17) | 0.052 (2) | 0.0005 (12) | −0.0098 (14) | −0.0234 (16) |
C13 | 0.0267 (14) | 0.0286 (15) | 0.0361 (17) | −0.0015 (12) | −0.0129 (13) | −0.0131 (13) |
C14 | 0.0278 (15) | 0.0263 (14) | 0.0412 (18) | −0.0008 (12) | −0.0115 (13) | −0.0140 (13) |
C15 | 0.0377 (18) | 0.0273 (16) | 0.060 (2) | −0.0044 (13) | −0.0153 (16) | −0.0172 (16) |
C16 | 0.045 (2) | 0.0293 (16) | 0.064 (2) | 0.0041 (14) | −0.0206 (18) | −0.0236 (17) |
C17 | 0.0334 (17) | 0.0384 (18) | 0.060 (2) | 0.0063 (14) | −0.0105 (16) | −0.0251 (17) |
C18 | 0.0278 (16) | 0.0349 (17) | 0.053 (2) | −0.0021 (13) | −0.0063 (15) | −0.0185 (16) |
C19 | 0.0290 (15) | 0.0249 (14) | 0.0373 (17) | −0.0006 (11) | −0.0110 (13) | −0.0133 (13) |
Geometric parameters (Å, º) top
Cd1—N3 | 2.266 (2) | C3—H3 | 0.9300 |
Cd1—N1 | 2.306 (3) | C4—C5 | 1.374 (5) |
Cd1—O1 | 2.350 (3) | C4—H4 | 0.9300 |
Cd1—O2 | 2.506 (3) | C5—C6 | 1.370 (5) |
Cd1—Cl1i | 2.5551 (10) | C5—H5 | 0.9300 |
Cd1—Cl1 | 2.6605 (13) | C6—C7 | 1.404 (5) |
Cd1—C1 | 2.756 (3) | C6—H6 | 0.9300 |
Cl1—Cd1i | 2.5550 (10) | C7—C8 | 1.533 (5) |
O1—C1 | 1.197 (4) | C9—H9 | 0.9300 |
O2—C1 | 1.242 (4) | C10—C11 | 1.343 (5) |
O3—C8 | 1.294 (4) | C10—H10 | 0.9300 |
O3—H3A | 0.8200 | C11—H11 | 0.9300 |
O4—C8 | 1.211 (4) | C12—C13ii | 1.492 (4) |
N1—C9 | 1.315 (4) | C12—H12A | 0.9700 |
N1—C10 | 1.359 (5) | C12—H12B | 0.9700 |
N2—C9 | 1.332 (4) | C13—C12iii | 1.492 (4) |
N2—C11 | 1.366 (4) | C14—C19 | 1.385 (4) |
N2—C12 | 1.459 (4) | C14—C15 | 1.389 (4) |
N3—C13 | 1.316 (4) | C15—C16 | 1.372 (5) |
N3—C19 | 1.400 (3) | C15—H15 | 0.9300 |
N4—C13 | 1.349 (4) | C16—C17 | 1.394 (5) |
N4—C14 | 1.383 (4) | C16—H16 | 0.9300 |
N4—H4A | 0.8600 | C17—C18 | 1.377 (4) |
C1—C2 | 1.553 (4) | C17—H17 | 0.9300 |
C2—C3 | 1.404 (4) | C18—C19 | 1.392 (4) |
C2—C7 | 1.412 (4) | C18—H18 | 0.9300 |
C3—C4 | 1.364 (5) | | |
| | | |
N3—Cd1—N1 | 93.26 (9) | C3—C4—H4 | 120.2 |
N3—Cd1—O1 | 145.11 (9) | C5—C4—H4 | 120.2 |
N1—Cd1—O1 | 83.65 (9) | C6—C5—C4 | 120.0 (4) |
N3—Cd1—O2 | 93.14 (9) | C6—C5—H5 | 120.0 |
N1—Cd1—O2 | 90.98 (9) | C4—C5—H5 | 120.0 |
O1—Cd1—O2 | 52.34 (8) | C5—C6—C7 | 121.8 (4) |
N3—Cd1—Cl1i | 110.50 (7) | C5—C6—H6 | 119.1 |
N1—Cd1—Cl1i | 92.18 (7) | C7—C6—H6 | 119.1 |
O1—Cd1—Cl1i | 104.36 (7) | C6—C7—C2 | 118.1 (3) |
O2—Cd1—Cl1i | 155.92 (6) | C6—C7—C8 | 112.8 (3) |
N3—Cd1—Cl1 | 96.35 (7) | C2—C7—C8 | 129.0 (3) |
N1—Cd1—Cl1 | 170.33 (7) | O4—C8—O3 | 119.6 (3) |
O1—Cd1—Cl1 | 89.04 (7) | O4—C8—C7 | 119.5 (4) |
O2—Cd1—Cl1 | 89.54 (6) | O3—C8—C7 | 120.9 (3) |
Cl1i—Cd1—Cl1 | 83.49 (3) | N1—C9—N2 | 111.6 (3) |
N3—Cd1—C1 | 119.75 (9) | N1—C9—H9 | 124.2 |
N1—Cd1—C1 | 86.69 (9) | N2—C9—H9 | 124.2 |
O1—Cd1—C1 | 25.56 (8) | C11—C10—N1 | 110.2 (3) |
O2—Cd1—C1 | 26.78 (8) | C11—C10—H10 | 124.9 |
Cl1i—Cd1—C1 | 129.73 (7) | N1—C10—H10 | 124.9 |
Cl1—Cd1—C1 | 89.44 (6) | C10—C11—N2 | 106.0 (3) |
Cd1i—Cl1—Cd1 | 96.51 (3) | C10—C11—H11 | 127.0 |
C1—O1—Cd1 | 96.5 (2) | N2—C11—H11 | 127.0 |
C1—O2—Cd1 | 87.9 (2) | N2—C12—C13ii | 113.8 (2) |
C8—O3—H3A | 109.5 | N2—C12—H12A | 108.8 |
C9—N1—C10 | 105.2 (3) | C13ii—C12—H12A | 108.8 |
C9—N1—Cd1 | 129.7 (2) | N2—C12—H12B | 108.8 |
C10—N1—Cd1 | 124.7 (2) | C13ii—C12—H12B | 108.8 |
C9—N2—C11 | 106.9 (3) | H12A—C12—H12B | 107.7 |
C9—N2—C12 | 126.7 (3) | N3—C13—N4 | 112.2 (3) |
C11—N2—C12 | 126.3 (3) | N3—C13—C12iii | 123.6 (3) |
C13—N3—C19 | 105.4 (2) | N4—C13—C12iii | 124.1 (3) |
C13—N3—Cd1 | 130.38 (19) | N4—C14—C19 | 105.4 (2) |
C19—N3—Cd1 | 123.57 (18) | N4—C14—C15 | 132.0 (3) |
C13—N4—C14 | 107.7 (2) | C19—C14—C15 | 122.6 (3) |
C13—N4—H4A | 126.1 | C16—C15—C14 | 116.6 (3) |
C14—N4—H4A | 126.1 | C16—C15—H15 | 121.7 |
O1—C1—O2 | 123.2 (3) | C14—C15—H15 | 121.7 |
O1—C1—C2 | 117.6 (3) | C15—C16—C17 | 121.6 (3) |
O2—C1—C2 | 119.1 (3) | C15—C16—H16 | 119.2 |
O1—C1—Cd1 | 57.90 (17) | C17—C16—H16 | 119.2 |
O2—C1—Cd1 | 65.35 (18) | C18—C17—C16 | 121.5 (3) |
C2—C1—Cd1 | 175.0 (2) | C18—C17—H17 | 119.3 |
C3—C2—C7 | 118.0 (3) | C16—C17—H17 | 119.3 |
C3—C2—C1 | 113.3 (3) | C17—C18—C19 | 117.6 (3) |
C7—C2—C1 | 128.7 (3) | C17—C18—H18 | 121.2 |
C4—C3—C2 | 122.4 (3) | C19—C18—H18 | 121.2 |
C4—C3—H3 | 118.8 | C14—C19—C18 | 120.1 (3) |
C2—C3—H3 | 118.8 | C14—C19—N3 | 109.2 (2) |
C3—C4—C5 | 119.6 (4) | C18—C19—N3 | 130.7 (3) |
| | | |
Cd1—O1—C1—O2 | −1.1 (3) | N1—C10—C11—N2 | −0.1 (5) |
Cd1—O1—C1—C2 | 177.5 (2) | C9—N2—C11—C10 | 0.0 (4) |
Cd1—O2—C1—O1 | 1.0 (3) | C12—N2—C11—C10 | −179.2 (3) |
Cd1—O2—C1—C2 | −177.5 (2) | C9—N2—C12—C13ii | 98.3 (4) |
O1—C1—C2—C3 | −0.6 (4) | C11—N2—C12—C13ii | −82.7 (4) |
O2—C1—C2—C3 | 178.0 (3) | C19—N3—C13—N4 | 0.9 (3) |
O1—C1—C2—C7 | 179.4 (3) | Cd1—N3—C13—N4 | −170.2 (2) |
O2—C1—C2—C7 | −2.0 (5) | C19—N3—C13—C12iii | −175.0 (3) |
C7—C2—C3—C4 | −0.2 (5) | Cd1—N3—C13—C12iii | 13.9 (5) |
C1—C2—C3—C4 | 179.8 (3) | C14—N4—C13—N3 | −0.5 (4) |
C2—C3—C4—C5 | −0.7 (6) | C14—N4—C13—C12iii | 175.4 (3) |
C3—C4—C5—C6 | 1.2 (6) | C13—N4—C14—C19 | −0.2 (3) |
C4—C5—C6—C7 | −0.8 (6) | C13—N4—C14—C15 | −179.9 (3) |
C5—C6—C7—C2 | −0.1 (5) | N4—C14—C15—C16 | 179.3 (3) |
C5—C6—C7—C8 | −179.6 (3) | C19—C14—C15—C16 | −0.4 (5) |
C3—C2—C7—C6 | 0.6 (5) | C14—C15—C16—C17 | −0.4 (5) |
C1—C2—C7—C6 | −179.5 (3) | C15—C16—C17—C18 | 1.2 (6) |
C3—C2—C7—C8 | −179.9 (3) | C16—C17—C18—C19 | −1.0 (5) |
C1—C2—C7—C8 | 0.0 (5) | N4—C14—C19—C18 | −179.2 (3) |
C6—C7—C8—O4 | 1.4 (5) | C15—C14—C19—C18 | 0.6 (5) |
C2—C7—C8—O4 | −178.1 (4) | N4—C14—C19—N3 | 0.7 (3) |
C6—C7—C8—O3 | −178.6 (3) | C15—C14—C19—N3 | −179.5 (3) |
C2—C7—C8—O3 | 1.9 (6) | C17—C18—C19—C14 | 0.1 (5) |
C10—N1—C9—N2 | −0.2 (4) | C17—C18—C19—N3 | −179.8 (3) |
Cd1—N1—C9—N2 | −172.92 (19) | C13—N3—C19—C14 | −1.0 (3) |
C11—N2—C9—N1 | 0.2 (4) | Cd1—N3—C19—C14 | 170.8 (2) |
C12—N2—C9—N1 | 179.3 (3) | C13—N3—C19—C18 | 178.9 (3) |
C9—N1—C10—C11 | 0.2 (4) | Cd1—N3—C19—C18 | −9.3 (5) |
Cd1—N1—C10—C11 | 173.4 (3) | | |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−1, y, z; (iii) x+1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3A···O2 | 0.82 | 1.62 | 2.436 (3) | 179 |
N4—H4A···O3iv | 0.86 | 2.17 | 2.931 (4) | 147 |
Symmetry code: (iv) −x+1, −y+1, −z+1. |
Poly[[aqua(µ
2-benzene-1,3-dicarboxylato-
κ3O1,
O1':
O3){µ
2-2-[(1
H-imidazol-1-yl)methyl]-1
H-benzimidazole-
κ2N:
N'}cadmium(II)] dihydrate] (II)
top
Crystal data top
[Cd(C8H4O4)(C11H10N4)(H2O)]·2H2O | Z = 2 |
Mr = 528.79 | F(000) = 532 |
Triclinic, P1 | Dx = 1.723 Mg m−3 |
a = 8.9624 (18) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.256 (2) Å | Cell parameters from 3521 reflections |
c = 13.070 (3) Å | θ = 1.7–27.8° |
α = 96.13 (3)° | µ = 1.12 mm−1 |
β = 106.88 (3)° | T = 293 K |
γ = 113.57 (3)° | Prism, colourless |
V = 1019.1 (5) Å3 | 0.19 × 0.18 × 0.14 mm |
Data collection top
Rigaku Saturn diffractometer | 4811 independent reflections |
Radiation source: fine-focus sealed tube | 4470 reflections with I > 2σ(I) |
Detector resolution: 28.5714 pixels mm-1 | Rint = 0.028 |
ω scans | θmax = 27.9°, θmin = 2.2° |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004) | h = −11→11 |
Tmin = 0.888, Tmax = 1.000 | k = −13→13 |
12704 measured reflections | l = −17→17 |
Refinement top
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: mixed |
wR(F2) = 0.066 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0227P)2 + 0.8447P] where P = (Fo2 + 2Fc2)/3 |
4811 reflections | (Δ/σ)max = 0.001 |
280 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.41 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cd1 | 0.68944 (2) | 0.12523 (2) | 0.21128 (2) | 0.02528 (6) | |
O1 | 0.6919 (3) | 0.3532 (2) | 0.20252 (17) | 0.0380 (4) | |
O2 | 0.7223 (3) | 0.2578 (2) | 0.05649 (18) | 0.0470 (5) | |
O3 | 0.6629 (3) | 0.8389 (3) | 0.23059 (18) | 0.0516 (6) | |
O4 | 0.7067 (3) | 0.9521 (2) | 0.10100 (16) | 0.0372 (4) | |
O5 | 0.3880 (2) | −0.0067 (2) | 0.10119 (15) | 0.0360 (4) | |
H5A | 0.3619 | −0.0952 | 0.0732 | 0.054* | |
H5B | 0.3563 | 0.0238 | 0.0447 | 0.054* | |
N1 | 0.9928 (3) | 0.2305 (2) | 0.28645 (19) | 0.0318 (5) | |
N2 | 1.2513 (3) | 0.2510 (2) | 0.29902 (17) | 0.0291 (5) | |
N3 | 0.6203 (3) | 0.1540 (2) | 0.36356 (16) | 0.0259 (4) | |
N4 | 0.5000 (3) | 0.2142 (3) | 0.47502 (17) | 0.0311 (5) | |
H4C | 0.4305 | 0.2388 | 0.4962 | 0.037* | |
C1 | 1.0802 (3) | 0.1616 (3) | 0.2643 (2) | 0.0326 (6) | |
H1 | 1.0290 | 0.0623 | 0.2288 | 0.039* | |
C2 | 1.1158 (4) | 0.3728 (4) | 0.3365 (3) | 0.0444 (7) | |
H2 | 1.0928 | 0.4485 | 0.3615 | 0.053* | |
C3 | 1.2755 (4) | 0.3875 (3) | 0.3445 (3) | 0.0443 (7) | |
H3 | 1.3807 | 0.4732 | 0.3748 | 0.053* | |
C4 | 1.3791 (4) | 0.2113 (4) | 0.2755 (2) | 0.0372 (7) | |
H4A | 1.4488 | 0.2870 | 0.2470 | 0.045* | |
H4B | 1.3169 | 0.1203 | 0.2177 | 0.045* | |
C5 | 0.4994 (3) | 0.1919 (3) | 0.3718 (2) | 0.0274 (5) | |
C6 | 0.6330 (3) | 0.1902 (3) | 0.5405 (2) | 0.0294 (5) | |
C7 | 0.6936 (4) | 0.2002 (3) | 0.6534 (2) | 0.0409 (7) | |
H7 | 0.6417 | 0.2242 | 0.6997 | 0.049* | |
C8 | 0.8353 (4) | 0.1724 (4) | 0.6923 (2) | 0.0489 (8) | |
H8 | 0.8818 | 0.1796 | 0.7674 | 0.059* | |
C9 | 0.9112 (4) | 0.1341 (4) | 0.6230 (3) | 0.0471 (8) | |
H9 | 1.0065 | 0.1161 | 0.6530 | 0.057* | |
C10 | 0.8489 (4) | 0.1220 (3) | 0.5109 (2) | 0.0370 (6) | |
H10 | 0.8987 | 0.0945 | 0.4646 | 0.044* | |
C11 | 0.7082 (3) | 0.1527 (3) | 0.4703 (2) | 0.0277 (5) | |
C12 | 0.7150 (3) | 0.3602 (3) | 0.1122 (2) | 0.0294 (5) | |
C13 | 0.7389 (3) | 0.4968 (3) | 0.0734 (2) | 0.0276 (5) | |
C14 | 0.8044 (4) | 0.5227 (3) | −0.0100 (2) | 0.0403 (7) | |
H14 | 0.8262 | 0.4522 | −0.0450 | 0.048* | |
C15 | 0.8375 (5) | 0.6523 (4) | −0.0414 (3) | 0.0517 (9) | |
H15 | 0.8853 | 0.6706 | −0.0958 | 0.062* | |
C16 | 0.7996 (4) | 0.7556 (3) | 0.0080 (2) | 0.0407 (7) | |
H16 | 0.8210 | 0.8426 | −0.0140 | 0.049* | |
C17 | 0.7299 (3) | 0.7302 (3) | 0.0900 (2) | 0.0280 (5) | |
C18 | 0.7018 (3) | 0.6010 (3) | 0.1230 (2) | 0.0269 (5) | |
H18 | 0.6576 | 0.5838 | 0.1790 | 0.032* | |
C19 | 0.6940 (3) | 0.8451 (3) | 0.1449 (2) | 0.0312 (6) | |
O6 | 0.6667 (3) | 0.7024 (3) | 0.4051 (2) | 0.0616 (7) | |
H6A | 0.6691 | 0.7430 | 0.3518 | 0.092* | |
H6B | 0.7357 | 0.6706 | 0.4396 | 0.092* | |
O7 | 0.8453 (5) | 0.5288 (3) | 0.4128 (2) | 0.0909 (10) | |
H7A | 0.8067 | 0.4604 | 0.3551 | 0.136* | |
H7B | 0.9044 | 0.5982 | 0.3892 | 0.136* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cd1 | 0.02621 (10) | 0.02688 (10) | 0.02839 (10) | 0.01539 (8) | 0.01257 (7) | 0.00763 (7) |
O1 | 0.0502 (12) | 0.0338 (10) | 0.0451 (11) | 0.0250 (9) | 0.0259 (10) | 0.0200 (9) |
O2 | 0.0682 (15) | 0.0280 (10) | 0.0486 (13) | 0.0293 (11) | 0.0174 (11) | 0.0047 (9) |
O3 | 0.0832 (17) | 0.0559 (14) | 0.0469 (13) | 0.0510 (13) | 0.0365 (12) | 0.0184 (11) |
O4 | 0.0485 (12) | 0.0273 (10) | 0.0414 (11) | 0.0252 (9) | 0.0130 (9) | 0.0078 (8) |
O5 | 0.0382 (11) | 0.0339 (10) | 0.0323 (10) | 0.0184 (9) | 0.0079 (8) | 0.0002 (8) |
N1 | 0.0242 (11) | 0.0362 (12) | 0.0399 (12) | 0.0169 (10) | 0.0134 (10) | 0.0105 (10) |
N2 | 0.0237 (11) | 0.0392 (13) | 0.0297 (11) | 0.0184 (10) | 0.0112 (9) | 0.0085 (10) |
N3 | 0.0244 (10) | 0.0326 (11) | 0.0269 (10) | 0.0165 (9) | 0.0119 (9) | 0.0094 (9) |
N4 | 0.0281 (11) | 0.0443 (13) | 0.0283 (11) | 0.0210 (10) | 0.0139 (9) | 0.0084 (10) |
C1 | 0.0280 (13) | 0.0332 (14) | 0.0402 (15) | 0.0174 (11) | 0.0120 (11) | 0.0104 (12) |
C2 | 0.0387 (17) | 0.0456 (18) | 0.0492 (18) | 0.0254 (14) | 0.0125 (14) | −0.0031 (14) |
C3 | 0.0286 (15) | 0.0368 (16) | 0.0544 (19) | 0.0110 (12) | 0.0078 (13) | −0.0029 (14) |
C4 | 0.0300 (14) | 0.064 (2) | 0.0299 (13) | 0.0314 (14) | 0.0136 (11) | 0.0125 (13) |
C5 | 0.0220 (12) | 0.0344 (14) | 0.0282 (12) | 0.0139 (10) | 0.0110 (10) | 0.0073 (11) |
C6 | 0.0264 (13) | 0.0318 (14) | 0.0283 (13) | 0.0118 (11) | 0.0096 (10) | 0.0072 (11) |
C7 | 0.0423 (17) | 0.0493 (18) | 0.0304 (14) | 0.0193 (14) | 0.0138 (13) | 0.0123 (13) |
C8 | 0.0442 (18) | 0.066 (2) | 0.0324 (15) | 0.0225 (16) | 0.0080 (13) | 0.0244 (15) |
C9 | 0.0316 (16) | 0.066 (2) | 0.0485 (18) | 0.0263 (15) | 0.0099 (13) | 0.0308 (16) |
C10 | 0.0313 (14) | 0.0462 (17) | 0.0438 (16) | 0.0227 (13) | 0.0166 (12) | 0.0210 (14) |
C11 | 0.0215 (12) | 0.0301 (13) | 0.0305 (13) | 0.0103 (10) | 0.0091 (10) | 0.0108 (11) |
C12 | 0.0241 (12) | 0.0224 (12) | 0.0393 (14) | 0.0122 (10) | 0.0063 (11) | 0.0066 (11) |
C13 | 0.0310 (13) | 0.0240 (12) | 0.0295 (13) | 0.0161 (11) | 0.0081 (10) | 0.0067 (10) |
C14 | 0.064 (2) | 0.0416 (16) | 0.0393 (15) | 0.0390 (15) | 0.0277 (15) | 0.0156 (13) |
C15 | 0.088 (3) | 0.059 (2) | 0.0500 (18) | 0.053 (2) | 0.0483 (19) | 0.0333 (17) |
C16 | 0.060 (2) | 0.0386 (16) | 0.0439 (16) | 0.0333 (15) | 0.0263 (15) | 0.0229 (13) |
C17 | 0.0298 (13) | 0.0260 (13) | 0.0313 (13) | 0.0174 (11) | 0.0088 (11) | 0.0068 (10) |
C18 | 0.0292 (13) | 0.0264 (13) | 0.0296 (13) | 0.0160 (11) | 0.0120 (10) | 0.0074 (10) |
C19 | 0.0305 (14) | 0.0278 (13) | 0.0341 (14) | 0.0185 (11) | 0.0046 (11) | 0.0031 (11) |
O6 | 0.0771 (17) | 0.0895 (19) | 0.0635 (15) | 0.0585 (16) | 0.0505 (14) | 0.0381 (14) |
O7 | 0.139 (3) | 0.0602 (18) | 0.0689 (19) | 0.0509 (19) | 0.0290 (19) | 0.0007 (15) |
Geometric parameters (Å, º) top
Cd1—O4i | 2.2487 (19) | C4—H4B | 0.9700 |
Cd1—N3 | 2.274 (2) | C5—C4iv | 1.491 (3) |
Cd1—N1 | 2.323 (2) | C6—C11 | 1.392 (3) |
Cd1—O1 | 2.3450 (19) | C6—C7 | 1.393 (4) |
Cd1—O5 | 2.367 (2) | C7—C8 | 1.378 (4) |
Cd1—O2 | 2.577 (2) | C7—H7 | 0.9300 |
O1—C12 | 1.261 (3) | C8—C9 | 1.390 (5) |
O2—C12 | 1.248 (3) | C8—H8 | 0.9300 |
O3—C19 | 1.232 (3) | C9—C10 | 1.380 (4) |
O4—C19 | 1.273 (3) | C9—H9 | 0.9300 |
O4—Cd1ii | 2.2487 (19) | C10—C11 | 1.391 (3) |
O5—H5A | 0.8500 | C10—H10 | 0.9300 |
O5—H5B | 0.8501 | C12—C13 | 1.497 (4) |
N1—C1 | 1.314 (3) | C13—C14 | 1.384 (4) |
N1—C2 | 1.366 (4) | C13—C18 | 1.390 (3) |
N2—C1 | 1.334 (3) | C14—C15 | 1.377 (4) |
N2—C3 | 1.365 (4) | C14—H14 | 0.9300 |
N2—C4 | 1.457 (3) | C15—C16 | 1.387 (4) |
N3—C5 | 1.316 (3) | C15—H15 | 0.9300 |
N3—C11 | 1.394 (3) | C16—C17 | 1.388 (4) |
N4—C5 | 1.342 (3) | C16—H16 | 0.9300 |
N4—C6 | 1.379 (3) | C17—C18 | 1.387 (3) |
N4—H4C | 0.8599 | C17—C19 | 1.505 (3) |
C1—H1 | 0.9300 | C18—H18 | 0.9300 |
C2—C3 | 1.349 (4) | O6—H6A | 0.8501 |
C2—H2 | 0.9300 | O6—H6B | 0.8500 |
C3—H3 | 0.9300 | O7—H7A | 0.8500 |
C4—C5iii | 1.491 (3) | O7—H7B | 0.8500 |
C4—H4A | 0.9700 | | |
| | | |
O4i—Cd1—N3 | 139.23 (8) | N3—C5—N4 | 113.1 (2) |
O4i—Cd1—N1 | 85.63 (8) | N3—C5—C4iv | 122.4 (2) |
N3—Cd1—N1 | 102.23 (8) | N4—C5—C4iv | 124.5 (2) |
O4i—Cd1—O1 | 135.48 (7) | N4—C6—C11 | 105.8 (2) |
N3—Cd1—O1 | 84.65 (8) | N4—C6—C7 | 131.5 (3) |
N1—Cd1—O1 | 92.40 (8) | C11—C6—C7 | 122.6 (3) |
O4i—Cd1—O5 | 82.68 (8) | C8—C7—C6 | 115.8 (3) |
N3—Cd1—O5 | 89.69 (8) | C8—C7—H7 | 122.1 |
N1—Cd1—O5 | 167.43 (7) | C6—C7—H7 | 122.1 |
O1—Cd1—O5 | 92.68 (8) | C7—C8—C9 | 122.2 (3) |
O4i—Cd1—O2 | 82.93 (7) | C7—C8—H8 | 118.9 |
N3—Cd1—O2 | 136.73 (7) | C9—C8—H8 | 118.9 |
N1—Cd1—O2 | 87.33 (8) | C10—C9—C8 | 121.8 (3) |
O1—Cd1—O2 | 52.56 (7) | C10—C9—H9 | 119.1 |
O5—Cd1—O2 | 86.65 (8) | C8—C9—H9 | 119.1 |
C12—O1—Cd1 | 98.23 (16) | C9—C10—C11 | 116.9 (3) |
C12—O2—Cd1 | 87.68 (17) | C9—C10—H10 | 121.5 |
C19—O4—Cd1ii | 109.56 (17) | C11—C10—H10 | 121.5 |
Cd1—O5—H5A | 110.5 | C6—C11—C10 | 120.6 (2) |
Cd1—O5—H5B | 114.5 | C6—C11—N3 | 108.8 (2) |
H5A—O5—H5B | 102.9 | C10—C11—N3 | 130.5 (2) |
C1—N1—C2 | 105.0 (2) | O2—C12—O1 | 121.5 (2) |
C1—N1—Cd1 | 122.19 (19) | O2—C12—C13 | 119.9 (3) |
C2—N1—Cd1 | 131.29 (18) | O1—C12—C13 | 118.6 (2) |
C1—N2—C3 | 106.9 (2) | C14—C13—C18 | 119.4 (2) |
C1—N2—C4 | 124.8 (2) | C14—C13—C12 | 119.8 (2) |
C3—N2—C4 | 127.7 (2) | C18—C13—C12 | 120.8 (2) |
C5—N3—C11 | 105.2 (2) | C15—C14—C13 | 120.3 (3) |
C5—N3—Cd1 | 126.60 (17) | C15—C14—H14 | 119.9 |
C11—N3—Cd1 | 127.82 (16) | C13—C14—H14 | 119.9 |
C5—N4—C6 | 107.1 (2) | C14—C15—C16 | 120.0 (3) |
C5—N4—H4C | 126.4 | C14—C15—H15 | 120.0 |
C6—N4—H4C | 126.5 | C16—C15—H15 | 120.0 |
N1—C1—N2 | 112.0 (2) | C15—C16—C17 | 120.5 (3) |
N1—C1—H1 | 124.0 | C15—C16—H16 | 119.8 |
N2—C1—H1 | 124.0 | C17—C16—H16 | 119.8 |
C3—C2—N1 | 110.1 (3) | C18—C17—C16 | 118.8 (2) |
C3—C2—H2 | 125.0 | C18—C17—C19 | 121.3 (2) |
N1—C2—H2 | 125.0 | C16—C17—C19 | 119.8 (2) |
C2—C3—N2 | 106.1 (3) | C17—C18—C13 | 120.9 (2) |
C2—C3—H3 | 127.0 | C17—C18—H18 | 119.6 |
N2—C3—H3 | 127.0 | C13—C18—H18 | 119.6 |
N2—C4—C5iii | 115.1 (2) | O3—C19—O4 | 122.3 (2) |
N2—C4—H4A | 108.5 | O3—C19—C17 | 121.5 (2) |
C5iii—C4—H4A | 108.5 | O4—C19—C17 | 116.2 (2) |
N2—C4—H4B | 108.5 | H6A—O6—H6B | 129.3 |
C5iii—C4—H4B | 108.5 | H7A—O7—H7B | 96.6 |
H4A—C4—H4B | 107.5 | | |
| | | |
C2—N1—C1—N2 | 1.1 (3) | C9—C10—C11—N3 | 178.2 (3) |
Cd1—N1—C1—N2 | 168.39 (17) | C5—N3—C11—C6 | 0.5 (3) |
C3—N2—C1—N1 | −1.3 (3) | Cd1—N3—C11—C6 | 173.58 (17) |
C4—N2—C1—N1 | −172.7 (2) | C5—N3—C11—C10 | −179.2 (3) |
C1—N1—C2—C3 | −0.4 (4) | Cd1—N3—C11—C10 | −6.1 (4) |
Cd1—N1—C2—C3 | −166.1 (2) | Cd1—O2—C12—O1 | −2.4 (3) |
N1—C2—C3—N2 | −0.4 (4) | Cd1—O2—C12—C13 | 175.9 (2) |
C1—N2—C3—C2 | 1.0 (3) | Cd1—O1—C12—O2 | 2.6 (3) |
C4—N2—C3—C2 | 172.1 (3) | Cd1—O1—C12—C13 | −175.69 (19) |
C1—N2—C4—C5iii | −108.5 (3) | O2—C12—C13—C14 | −13.5 (4) |
C3—N2—C4—C5iii | 81.9 (4) | O1—C12—C13—C14 | 164.9 (3) |
C11—N3—C5—N4 | −0.6 (3) | O2—C12—C13—C18 | 168.8 (2) |
Cd1—N3—C5—N4 | −173.83 (16) | O1—C12—C13—C18 | −12.8 (4) |
C11—N3—C5—C4iv | 177.9 (2) | C18—C13—C14—C15 | 1.9 (4) |
Cd1—N3—C5—C4iv | 4.6 (4) | C12—C13—C14—C15 | −175.8 (3) |
C6—N4—C5—N3 | 0.5 (3) | C13—C14—C15—C16 | −2.2 (5) |
C6—N4—C5—C4iv | −177.9 (3) | C14—C15—C16—C17 | 0.7 (5) |
C5—N4—C6—C11 | −0.2 (3) | C15—C16—C17—C18 | 1.1 (4) |
C5—N4—C6—C7 | 178.7 (3) | C15—C16—C17—C19 | 178.4 (3) |
N4—C6—C7—C8 | −177.9 (3) | C16—C17—C18—C13 | −1.4 (4) |
C11—C6—C7—C8 | 0.8 (4) | C19—C17—C18—C13 | −178.6 (2) |
C6—C7—C8—C9 | −1.1 (5) | C14—C13—C18—C17 | −0.1 (4) |
C7—C8—C9—C10 | 0.2 (5) | C12—C13—C18—C17 | 177.6 (2) |
C8—C9—C10—C11 | 1.2 (5) | Cd1ii—O4—C19—O3 | 5.2 (3) |
N4—C6—C11—C10 | 179.6 (2) | Cd1ii—O4—C19—C17 | −171.14 (17) |
C7—C6—C11—C10 | 0.6 (4) | C18—C17—C19—O3 | 10.7 (4) |
N4—C6—C11—N3 | −0.2 (3) | C16—C17—C19—O3 | −166.6 (3) |
C7—C6—C11—N3 | −179.2 (2) | C18—C17—C19—O4 | −172.9 (2) |
C9—C10—C11—C6 | −1.5 (4) | C16—C17—C19—O4 | 9.8 (4) |
Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z; (iii) x+1, y, z; (iv) x−1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4C···O6v | 0.86 | 1.92 | 2.741 (3) | 159 |
O5—H5A···O2vi | 0.85 | 1.97 | 2.739 (3) | 151 |
O5—H5B···O4vii | 0.85 | 1.90 | 2.722 (3) | 164 |
O6—H6A···O3 | 0.85 | 1.95 | 2.800 (3) | 176 |
O6—H6B···O7 | 0.85 | 2.11 | 2.823 (4) | 142 |
O7—H7A···O1 | 0.85 | 1.92 | 2.730 (4) | 160 |
Symmetry codes: (v) −x+1, −y+1, −z+1; (vi) −x+1, −y, −z; (vii) −x+1, −y+1, −z. |