In the title cadmium complex of 3-nitrobenzoate and 3-cyanopyridine, binuclear centrosymmetric molecules are present, with cadmium being surrounded in an N2O5 coordinaton set in a distorted pentagonal–bipyramidal shape.
Keywords: crystal structure, cadmium, transition metal complex, benzoic acid
Abstract
The asymmetric unit of the title compound, [Cd2(C7H4NO4)4(C6H4N2)4], contains one CdII atom, two 3-nitrobenzoate (NB) anions and two 3-cyanopyridine (CPy) ligands. The two CPy ligands act as monodentate N(pyridine)-bonding ligands, while the two NB anions act as bidentate ligands through the carboxylate O atoms. The centrosymmetric dinuclear complex is generated by application of inversion symmetry, whereby the CdII atoms are bridged by the carboxylate O atoms of two symmetry-related NB anions, thus completing the distorted N2O5 pentagonal–bipyramidal coordination sphere of each CdII atom. The benzene and pyridine rings are oriented at dihedral angles of 10.02 (7) and 5.76 (9)°, respectively. In the crystal, C—H⋯N hydrogen bonds link the molecules, enclosing R 2 2(26) ring motifs, in which they are further linked via C—H⋯O hydrogen bonds, resulting in a three-dimensional network. In addition, π–π stacking interactions between parallel benzene rings and between parallel pyridine rings of adjacent molecules [shortest centroid-to-centroid distances = 3.885 (1) and 3.712 (1) Å, respectively], as well as a weak C—H⋯π interaction, may further stabilize the crystal structure.
Chemical context
In the last two decades, research on metal–organic frameworks (MOFs) has received considerable attention due to their extensive structural chemistry (Li et al., 2016 ▸) and their potential applications, including gas storage, nonlinear optics and ion exchange (Carlucci et al., 2003 ▸). In the syntheses of compounds having MOF structures, various carboxylate ligands have been used (Li et al., 2004 ▸).
On the other hand, transition-metal complexes with biochemically active molecules show interesting physical and/or chemical properties, through which they may find applications in biological systems (Antolini et al., 1982 ▸). Some benzoic acid derivatives, such as 4-aminobenzoic acid, have been extensively reported in coordination chemistry, as bifunctional organic ligands, due to the varieties of their coordination modes (Chen & Chen, 2002 ▸; Amiraslanov et al., 1979 ▸; Hauptmann et al., 2000 ▸).
The structure–function–coordination relationships of arylcarboxylate ions in ZnII complexes of benzoic acid derivatives change depending on the nature and position of the substituted groups on the benzene ring, the nature of the additional ligand molecule or solvent, and the pH range and temperature of the synthesis (Shnulin et al., 1981 ▸; Nadzhafov et al., 1981 ▸; Antsyshkina et al., 1980 ▸; Adiwidjaja et al., 1978 ▸). When pyridine and its derivatives are used instead of water molecules, the structure is completely different (Catterick et al., 1974 ▸).
The structures of some dinuclear complexes obtained from the reactions of transition metal(II) ions with nicotinamide (NA; C6H6N2O) and some benzoic acid derivatives as ligands, e.g. [Zn2(C7H4FO2)4(C6H6N2O)2]·C7H5FO2 [(II); Hökelek et al., 2009 ▸], [Cu2(C8H7O3)4(C6H6N2O)2(H2O)2] [(III); Hökelek et al., 2010 ▸], [Cu2(C8H5O3)4(C6H6N2O)4] [(IV); Sertçelik et al., 2013 ▸], [Mn2(C7H4BrO2)4(C6H6N2O)2(H2O)2] [(V); Necefoğlu et al., 2011 ▸] and [Cd2(C7H4ClO2)4(C6H6N2O)2(H2O)2] [(VI); Bozkurt et al., 2013 ▸], have been determined previously. In this context, we have synthesized the CdII-containing title compound, bis(μ-3-nitrobenzoato)-κ3 O,O′:O;κ3 O:O,O′-bis[bis(3-cyanopyridine-κN)(3-nitrobenzoato-κ2 O,O′)cadmium], [Cd2(C7H4NO4)4(C6H4N2)4], and report herein its crystal structure.
Structural commentary
The asymmetric unit of the title complex contains one CdII atom, two 3-nitrobenzoate (NB) anions and two 3-cyanopyridine (CPy) ligands. The two CPy ligands are monodentate (through the pyridine N atoms), while both NB anions act as bidentate ligands through their carboxylate O atoms (Fig. 1 ▸). The centrosymmetric dinuclear molecule is completed by application of inversion symmerty. The CdII atoms are bridged by the carboxylate O atoms of one NB anions (O6 and O5) and its symmetry-related counterpart [symmetry code: (i) −x, −y + 1, −z + 1]. Hence, this carboxylate group not only chelates to one CdII atom but also bridges two CdII atoms (Fig. 2 ▸). Thus, each CdII atom is surrounded by three NB anions and two CPy ligands. The overall coordination sphere of the CdII atom is defined by the bridging/chelating NB anions (O5, O5i and O6), one chelating NB anion (O1 and O2) and two 3-cyanopyridine (CPy) ligands (N3 and N5), resulting in a distorted pentagonal–bipyramidal environment. The five carboxylate O atoms (O1, O2, O5, O5i and O6) of the three NB anions around the CdII atom form a distorted pentagonal arrangement, with an average Cd1—O bond length of 2.42 Å (Table 1 ▸). The distorted pentagonal–bipyramidal coordination is completed by pyridine atoms N3 and N5 of the CPy ligands at distances of 2.3186 (17) and 2.3435 (17) Å, respectively, in the axial positions (Table 1 ▸; Figs. 1 ▸ and 2 ▸). The Cd1 atom lies 0.1252 (1) Å above and 0.0326 (1) Å below of planar O1/O2/C1 and O5/O6/C8 carboxylate groups, respectively. The Cd1⋯Cd1i separation in the binuclear molecule is 3.9360 (15) Å and is comparable to the corresponding M—M distances (M is a metal) in the structurally related transition metal(II) complexes [7.1368 (3) Å in (III), 4.1554 (8) Å in (IV), 7.180 (2) Å in (V) and 7.1647 (3) Å in (VI)]. The metal atoms are bridged by two NA ligand N and O atoms in (III), (V) and (VI), while they are bridged by two carboxylate O atoms in (IV).
Figure 1.
The asymmetric unit of the title molecule, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Figure 2.
The molecular structure of the binuclear title molecule. Symmetry-related atoms are related by the symmetry code (−x, −y + 1, −z + 1). H atoms have been omitted for clarity.
Table 1. Selected bond lengths (Å).
| Cd1—O1 | 2.3017 (15) | Cd1—O6 | 2.3264 (15) |
| Cd1—O2 | 2.5072 (18) | Cd1—N3 | 2.3186 (17) |
| Cd1—O5 | 2.5367 (16) | Cd1—N5 | 2.3435 (17) |
| Cd1—O5i | 2.4716 (16) |
Symmetry code: (i) 
.
The near equalities of the C1—O1 [1.264 (3) Å], C1—O2 [1.241 (3) Å], C8—O5 [1.256 (3) Å] and C8—O6 [1.253 (3) Å] bonds in the carboxylate groups indicate delocalized bonding arrangements, rather than localized single and double bonds. The O1—Cd1—O2 and O5—Cd1—O6 bite angles are reduced to 54.33 (5) and 53.47 (5)°, respectively. The corresponding O—M—O (M is a divalent metal) angles are 60.92 (12)° in (II), 53.50 (14)° in (IV), 57.61 (8)° in (V), and 54.22 (4) and 53.32 (5)° in (VI). The dihedral angles between the planar carboxylate groups (O1/O2/C1 and O5/O6/C8) and the adjacent benzene [A (C2–C7) and B (C9–C14)] rings in the title structure are 17.18 (13) and 3.36 (12)°, respectively, while the benzene (A and B) and pyridine [C (N3/C15–C19) and D (N5/C21–C25)] rings are oriented at dihedral angles of A/B = 10.02 (7)°, A/C = 72.70 (7)°, A/D = 74.72 (7)°, B/C = 82.28 (7)°, B/D = 84.54 (8)° and C/D = 5.76 (9)°.
Supramolecular features
Intramolecular C—Hcpy⋯Oc (cpy = cyanopyridine and c = carboxylate) and C—Hnb⋯Oc (nb = nitrobenzoate) hydrogen bonds (Table 2 ▸) link the cyanopyridine and nitrobenzoate ligands to the carboxylate O atoms. In the crystal, C—Hcpy⋯Ncpy hydrogen bonds (Table 2 ▸) link the molecules, enclosing 
(26) ring motifs (Bernstein et al., 1995 ▸) (Fig. 3 ▸), in which they are further linked via additional C—Hcpy⋯Onb (nb = nitrobenzoate) hydrogen bonds (Table 2 ▸), resulting in a three-dimensional network. The π–π contacts between parallel benzene rings and between parallel pyridine rings of adjacent molecules, Cg1–Cg2i and Cg3–Cg4ii [symmetry codes: (i) −x + 1, −y + 1, −z + 1; (ii) −x, −y + 1, −z + 1; Cg1, Cg2, Cg3 and Cg4 are the centroids of the rings A (atoms C2–C7), B (C9–C14), C (N3/C15–C19) and D (N5/C21–C25)] may further stabilize the structure, with centroid–centroid distances of 3.885 (1) and 3.712 (1) Å, respectively. A weak C—H⋯π interaction (Table 2 ▸) is also observed.
Table 2. Hydrogen-bond geometry (Å, °).
Cg3 is the centroid of the N3/C15–C19 ring.
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| C14—H14⋯O1i | 0.93 | 2.20 | 3.108 (3) | 167 |
| C15—H15⋯O2ii | 0.93 | 2.32 | 3.111 (3) | 143 |
| C23—H23⋯N4iii | 0.93 | 2.38 | 3.236 (5) | 154 |
| C25—H25⋯O6 | 0.93 | 2.58 | 3.242 (3) | 128 |
| C10—H10⋯Cg3ii | 0.93 | 3.26 | 4.186 (3) | 176 |
Symmetry codes: (i) ; (ii) 
; (iii) 
.
Figure 3.
Part of the crystal structure. Intramolecular (C—Hcpy⋯Oc and C—Hnb⋯Oc) and intermolecular (C—Hcpy⋯Ncpy and C—Hcpy⋯Onb) (cpy = cyanopyridine, c = carboxylate and nb = nitrobenzoate) hydrogen bonds are shown as dashed lines. Nonbonding H atoms have been omitted for clarity.
Refinement
The experimental details including the crystal data, data collection and refinement are summarized in Table 3 ▸. Aromatic H atoms were positioned geometrically, with C—H = 0.93 Å, and constrained to ride on their parent atoms, with U iso(H) = 1.2U eq(C). The maximum and minimum electron densities were found at 1.43 and 0.80 Å from atoms O2 and Cd1, respectively.
Table 3. Experimental details.
| Crystal data | |
| Chemical formula | [Cd2(C7H4NO4)4(C6H4N2)4] |
| M r | 1305.72 |
| Crystal system, space group | Triclinic, P
|
| Temperature (K) | 296 |
| a, b, c (Å) | 8.5237 (3), 12.7145 (4), 13.0583 (5) |
| α, β, γ (°) | 105.022 (3), 97.347 (3), 104.866 (2) |
| V (Å3) | 1292.12 (8) |
| Z | 1 |
| Radiation type | Mo Kα |
| μ (mm−1) | 0.91 |
| Crystal size (mm) | 0.28 × 0.20 × 0.18 |
| Data collection | |
| Diffractometer | Bruker APEXII CCD |
| Absorption correction | Multi-scan (SADABS; Bruker, 2012 ▸) |
| T min, T max | 0.615, 0.746 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 65471, 6414, 5828 |
| R int | 0.029 |
| (sin θ/λ)max (Å−1) | 0.668 |
| Refinement | |
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.029, 0.072, 1.22 |
| No. of reflections | 6414 |
| No. of parameters | 370 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 1.01, −0.75 |
Synthesis and crystallization
The title compound was prepared by the reaction of 3CdSO4·8H2O (0.64 g, 2.5 mmol) in H2O (50 ml) and 3-cyanopyridine (0.52 g, 5 mmol) in H2O (50 ml) with sodium 3-nitrobenzoate (0.95 g, 5 mmol) in H2O (100 ml) at 333 K. The mixture was filtered and set aside to crystallize at ambient temperature for one week, giving colourless single crystals.
Supplementary Material
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989017002675/wm5366sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989017002675/wm5366Isup2.hkl
CCDC reference: 1533101
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors acknowledge the Scientific and Technological Research Application and Research Center, Sinop University, Turkey, for the use of the Bruker D8 QUEST diffractometer.
supplementary crystallographic information
Crystal data
| [Cd2(C7H4NO4)4(C6H4N2)4] | Z = 1 |
| Mr = 1305.72 | F(000) = 652 |
| Triclinic, P1 | Dx = 1.678 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 8.5237 (3) Å | Cell parameters from 9607 reflections |
| b = 12.7145 (4) Å | θ = 3.1–28.3° |
| c = 13.0583 (5) Å | µ = 0.91 mm−1 |
| α = 105.022 (3)° | T = 296 K |
| β = 97.347 (3)° | Prism, colourless |
| γ = 104.866 (2)° | 0.28 × 0.20 × 0.18 mm |
| V = 1292.12 (8) Å3 |
Data collection
| Bruker APEXII CCD diffractometer | 6414 independent reflections |
| Radiation source: fine-focus sealed tube | 5828 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.029 |
| φ and ω scans | θmax = 28.3°, θmin = 3.1° |
| Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −11→11 |
| Tmin = 0.615, Tmax = 0.746 | k = −16→16 |
| 65471 measured reflections | l = −17→17 |
Refinement
| 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)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.072 | H-atom parameters constrained |
| S = 1.22 | w = 1/[σ2(Fo2) + (0.0277P)2 + 0.8651P] where P = (Fo2 + 2Fc2)/3 |
| 6414 reflections | (Δ/σ)max = 0.001 |
| 370 parameters | Δρmax = 1.01 e Å−3 |
| 0 restraints | Δρmin = −0.75 e Å−3 |
Special details
| 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. |
| 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 > 2sigma(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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Cd1 | 0.151839 (18) | 0.436274 (11) | 0.419807 (11) | 0.03200 (6) | |
| O1 | 0.0821 (2) | 0.25149 (13) | 0.30752 (14) | 0.0448 (4) | |
| O2 | 0.3355 (2) | 0.35240 (13) | 0.30991 (15) | 0.0480 (4) | |
| O3 | −0.0992 (3) | −0.15593 (16) | 0.12938 (19) | 0.0675 (6) | |
| O4 | 0.0033 (3) | −0.22812 (15) | −0.00392 (17) | 0.0646 (5) | |
| O5 | 0.1364 (2) | 0.61626 (13) | 0.55320 (14) | 0.0431 (4) | |
| O6 | 0.3515 (2) | 0.61460 (13) | 0.47720 (13) | 0.0414 (3) | |
| O7 | 0.8058 (3) | 0.9744 (2) | 0.5573 (3) | 0.1093 (12) | |
| O8 | 0.7807 (3) | 1.13029 (18) | 0.6485 (3) | 0.0928 (9) | |
| N1 | 0.0007 (3) | −0.14806 (16) | 0.07056 (17) | 0.0435 (4) | |
| N2 | 0.7303 (3) | 1.02738 (18) | 0.6099 (2) | 0.0537 (5) | |
| N3 | 0.2275 (2) | 0.37248 (14) | 0.56414 (14) | 0.0320 (3) | |
| N4 | 0.6329 (5) | 0.5371 (3) | 0.8932 (3) | 0.1256 (18) | |
| N5 | 0.0320 (2) | 0.48389 (15) | 0.27322 (14) | 0.0358 (4) | |
| N6 | −0.3803 (3) | 0.2705 (2) | −0.0491 (2) | 0.0685 (7) | |
| C1 | 0.2174 (3) | 0.26302 (16) | 0.27548 (16) | 0.0324 (4) | |
| C2 | 0.2308 (3) | 0.16188 (17) | 0.19015 (17) | 0.0322 (4) | |
| C3 | 0.1160 (3) | 0.05585 (17) | 0.17155 (17) | 0.0330 (4) | |
| H3 | 0.0350 | 0.0469 | 0.2127 | 0.040* | |
| C4 | 0.1244 (3) | −0.03626 (17) | 0.09058 (17) | 0.0347 (4) | |
| C5 | 0.2408 (3) | −0.0262 (2) | 0.0267 (2) | 0.0459 (5) | |
| H5 | 0.2429 | −0.0892 | −0.0279 | 0.055* | |
| C6 | 0.3544 (4) | 0.0798 (2) | 0.0456 (2) | 0.0535 (6) | |
| H6 | 0.4340 | 0.0886 | 0.0034 | 0.064* | |
| C7 | 0.3498 (3) | 0.1736 (2) | 0.1279 (2) | 0.0447 (5) | |
| H7 | 0.4274 | 0.2445 | 0.1410 | 0.054* | |
| C8 | 0.2760 (2) | 0.66594 (16) | 0.53913 (16) | 0.0315 (4) | |
| C9 | 0.3550 (2) | 0.79211 (16) | 0.59657 (16) | 0.0312 (4) | |
| C10 | 0.5053 (3) | 0.84920 (17) | 0.57676 (18) | 0.0346 (4) | |
| H10 | 0.5592 | 0.8106 | 0.5294 | 0.042* | |
| C11 | 0.5721 (3) | 0.96539 (17) | 0.62989 (19) | 0.0384 (5) | |
| C12 | 0.4989 (3) | 1.02590 (19) | 0.7024 (2) | 0.0491 (6) | |
| H12 | 0.5479 | 1.1036 | 0.7373 | 0.059* | |
| C13 | 0.3506 (4) | 0.9677 (2) | 0.7217 (2) | 0.0565 (7) | |
| H13 | 0.2988 | 1.0064 | 0.7706 | 0.068* | |
| C14 | 0.2785 (3) | 0.8520 (2) | 0.6685 (2) | 0.0453 (5) | |
| H14 | 0.1776 | 0.8140 | 0.6811 | 0.054* | |
| C15 | 0.3517 (3) | 0.43881 (18) | 0.64654 (18) | 0.0360 (4) | |
| H15 | 0.4061 | 0.5123 | 0.6466 | 0.043* | |
| C16 | 0.4023 (3) | 0.4017 (2) | 0.73219 (19) | 0.0414 (5) | |
| C17 | 0.3240 (3) | 0.2918 (2) | 0.7327 (2) | 0.0479 (6) | |
| H17 | 0.3567 | 0.2653 | 0.7894 | 0.058* | |
| C18 | 0.1962 (3) | 0.2229 (2) | 0.6465 (2) | 0.0503 (6) | |
| H18 | 0.1411 | 0.1486 | 0.6437 | 0.060* | |
| C19 | 0.1517 (3) | 0.26648 (19) | 0.56478 (19) | 0.0417 (5) | |
| H19 | 0.0649 | 0.2200 | 0.5072 | 0.050* | |
| C20 | 0.5330 (4) | 0.4779 (3) | 0.8215 (3) | 0.0706 (10) | |
| C21 | −0.0872 (3) | 0.40583 (18) | 0.19319 (17) | 0.0375 (4) | |
| H21 | −0.1240 | 0.3318 | 0.1971 | 0.045* | |
| C22 | −0.1584 (3) | 0.43099 (19) | 0.10448 (17) | 0.0373 (4) | |
| C23 | −0.1049 (3) | 0.5416 (2) | 0.09792 (19) | 0.0462 (5) | |
| H23 | −0.1512 | 0.5609 | 0.0397 | 0.055* | |
| C24 | 0.0186 (4) | 0.6213 (2) | 0.1803 (2) | 0.0541 (7) | |
| H24 | 0.0579 | 0.6960 | 0.1787 | 0.065* | |
| C25 | 0.0835 (3) | 0.58913 (19) | 0.26552 (19) | 0.0460 (6) | |
| H25 | 0.1675 | 0.6438 | 0.3204 | 0.055* | |
| C26 | −0.2833 (3) | 0.3418 (2) | 0.0192 (2) | 0.0484 (6) |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cd1 | 0.03932 (9) | 0.02142 (7) | 0.02841 (8) | 0.00423 (6) | 0.00100 (6) | 0.00389 (5) |
| O1 | 0.0451 (9) | 0.0315 (8) | 0.0489 (9) | 0.0062 (7) | 0.0178 (7) | −0.0009 (7) |
| O2 | 0.0433 (9) | 0.0304 (8) | 0.0549 (10) | −0.0010 (7) | 0.0077 (8) | 0.0003 (7) |
| O3 | 0.0779 (14) | 0.0390 (10) | 0.0778 (14) | 0.0002 (9) | 0.0284 (12) | 0.0163 (10) |
| O4 | 0.0769 (14) | 0.0324 (9) | 0.0658 (13) | 0.0110 (9) | 0.0042 (10) | −0.0060 (8) |
| O5 | 0.0372 (8) | 0.0272 (7) | 0.0521 (9) | −0.0040 (6) | 0.0057 (7) | 0.0061 (7) |
| O6 | 0.0422 (8) | 0.0266 (7) | 0.0437 (8) | 0.0026 (6) | 0.0061 (7) | 0.0000 (6) |
| O7 | 0.0819 (17) | 0.0595 (14) | 0.155 (3) | −0.0138 (12) | 0.0739 (19) | −0.0093 (16) |
| O8 | 0.0713 (15) | 0.0345 (10) | 0.141 (2) | −0.0190 (10) | 0.0299 (15) | 0.0046 (13) |
| N1 | 0.0528 (11) | 0.0276 (9) | 0.0451 (11) | 0.0108 (8) | −0.0003 (9) | 0.0091 (8) |
| N2 | 0.0436 (11) | 0.0353 (10) | 0.0650 (14) | −0.0075 (9) | 0.0087 (10) | 0.0070 (10) |
| N3 | 0.0325 (8) | 0.0287 (8) | 0.0325 (8) | 0.0070 (7) | 0.0044 (7) | 0.0091 (7) |
| N4 | 0.136 (3) | 0.085 (2) | 0.103 (3) | −0.028 (2) | −0.077 (2) | 0.050 (2) |
| N5 | 0.0488 (10) | 0.0272 (8) | 0.0279 (8) | 0.0093 (7) | 0.0024 (7) | 0.0072 (7) |
| N6 | 0.0717 (16) | 0.0507 (14) | 0.0597 (15) | −0.0003 (12) | −0.0179 (13) | 0.0112 (12) |
| C1 | 0.0396 (10) | 0.0240 (9) | 0.0312 (9) | 0.0086 (8) | 0.0033 (8) | 0.0072 (7) |
| C2 | 0.0361 (10) | 0.0269 (9) | 0.0346 (10) | 0.0122 (8) | 0.0055 (8) | 0.0093 (8) |
| C3 | 0.0373 (10) | 0.0282 (9) | 0.0332 (10) | 0.0105 (8) | 0.0056 (8) | 0.0092 (8) |
| C4 | 0.0411 (11) | 0.0259 (9) | 0.0348 (10) | 0.0110 (8) | 0.0006 (8) | 0.0081 (8) |
| C5 | 0.0548 (14) | 0.0371 (11) | 0.0464 (13) | 0.0196 (10) | 0.0167 (11) | 0.0048 (10) |
| C6 | 0.0565 (15) | 0.0471 (14) | 0.0628 (16) | 0.0197 (12) | 0.0313 (13) | 0.0136 (12) |
| C7 | 0.0437 (12) | 0.0347 (11) | 0.0540 (14) | 0.0086 (9) | 0.0183 (10) | 0.0098 (10) |
| C8 | 0.0323 (9) | 0.0236 (9) | 0.0298 (9) | 0.0016 (7) | −0.0040 (7) | 0.0055 (7) |
| C9 | 0.0303 (9) | 0.0221 (8) | 0.0321 (9) | 0.0004 (7) | −0.0020 (7) | 0.0045 (7) |
| C10 | 0.0331 (10) | 0.0246 (9) | 0.0387 (11) | 0.0027 (7) | 0.0041 (8) | 0.0047 (8) |
| C11 | 0.0321 (10) | 0.0261 (9) | 0.0452 (12) | −0.0034 (8) | −0.0006 (9) | 0.0071 (8) |
| C12 | 0.0485 (13) | 0.0230 (10) | 0.0587 (15) | 0.0004 (9) | 0.0032 (11) | −0.0023 (10) |
| C13 | 0.0547 (15) | 0.0342 (12) | 0.0656 (17) | 0.0061 (11) | 0.0202 (13) | −0.0062 (11) |
| C14 | 0.0387 (11) | 0.0332 (11) | 0.0509 (13) | −0.0005 (9) | 0.0118 (10) | 0.0007 (10) |
| C15 | 0.0334 (10) | 0.0317 (10) | 0.0388 (11) | 0.0042 (8) | 0.0001 (8) | 0.0128 (8) |
| C16 | 0.0376 (11) | 0.0411 (12) | 0.0431 (12) | 0.0086 (9) | −0.0002 (9) | 0.0162 (10) |
| C17 | 0.0519 (14) | 0.0486 (13) | 0.0483 (13) | 0.0137 (11) | 0.0059 (11) | 0.0269 (11) |
| C18 | 0.0567 (15) | 0.0351 (12) | 0.0568 (15) | 0.0034 (10) | 0.0089 (12) | 0.0222 (11) |
| C19 | 0.0432 (12) | 0.0323 (10) | 0.0411 (12) | 0.0017 (9) | 0.0021 (9) | 0.0095 (9) |
| C20 | 0.0715 (19) | 0.0570 (17) | 0.0665 (19) | −0.0031 (14) | −0.0272 (16) | 0.0329 (15) |
| C21 | 0.0454 (12) | 0.0296 (10) | 0.0336 (10) | 0.0072 (9) | 0.0035 (9) | 0.0093 (8) |
| C22 | 0.0408 (11) | 0.0361 (11) | 0.0310 (10) | 0.0106 (9) | 0.0019 (8) | 0.0070 (8) |
| C23 | 0.0601 (15) | 0.0393 (12) | 0.0379 (11) | 0.0157 (11) | −0.0025 (10) | 0.0148 (10) |
| C24 | 0.0765 (18) | 0.0296 (11) | 0.0472 (13) | 0.0060 (11) | −0.0058 (12) | 0.0155 (10) |
| C25 | 0.0605 (15) | 0.0284 (10) | 0.0369 (11) | 0.0030 (10) | −0.0055 (10) | 0.0075 (9) |
| C26 | 0.0533 (14) | 0.0412 (12) | 0.0430 (12) | 0.0080 (11) | −0.0028 (11) | 0.0123 (10) |
Geometric parameters (Å, º)
| Cd1—O1 | 2.3017 (15) | C7—H7 | 0.9300 |
| Cd1—O2 | 2.5072 (18) | C8—C9 | 1.511 (3) |
| Cd1—O5 | 2.5367 (16) | C9—C10 | 1.393 (3) |
| Cd1—O5i | 2.4716 (16) | C9—C14 | 1.389 (3) |
| Cd1—O6 | 2.3264 (15) | C10—C11 | 1.387 (3) |
| Cd1—N3 | 2.3186 (17) | C10—H10 | 0.9300 |
| Cd1—N5 | 2.3435 (17) | C11—N2 | 1.470 (3) |
| Cd1—C1 | 2.733 (2) | C11—C12 | 1.377 (3) |
| O1—C1 | 1.264 (3) | C12—C13 | 1.381 (4) |
| O5—Cd1i | 2.4716 (16) | C12—H12 | 0.9300 |
| O5—C8 | 1.256 (3) | C13—H13 | 0.9300 |
| O6—C8 | 1.253 (3) | C14—C13 | 1.386 (3) |
| O8—N2 | 1.210 (3) | C14—H14 | 0.9300 |
| N1—O3 | 1.220 (3) | C15—C16 | 1.384 (3) |
| N1—O4 | 1.219 (3) | C15—H15 | 0.9300 |
| N1—C4 | 1.472 (3) | C16—C17 | 1.387 (3) |
| N2—O7 | 1.198 (3) | C16—C20 | 1.438 (4) |
| N3—C15 | 1.330 (3) | C17—H17 | 0.9300 |
| N3—C19 | 1.339 (3) | C18—C17 | 1.381 (4) |
| N4—C20 | 1.127 (4) | C18—H18 | 0.9300 |
| N5—C21 | 1.335 (3) | C19—C18 | 1.379 (3) |
| N5—C25 | 1.331 (3) | C19—H19 | 0.9300 |
| C1—O2 | 1.241 (3) | C21—C22 | 1.387 (3) |
| C1—C2 | 1.508 (3) | C21—H21 | 0.9300 |
| C2—C7 | 1.381 (3) | C22—C23 | 1.391 (3) |
| C3—C2 | 1.388 (3) | C22—C26 | 1.443 (3) |
| C3—C4 | 1.384 (3) | C23—C24 | 1.375 (3) |
| C3—H3 | 0.9300 | C23—H23 | 0.9300 |
| C4—C5 | 1.378 (3) | C24—H24 | 0.9300 |
| C5—C6 | 1.382 (4) | C25—C24 | 1.380 (3) |
| C5—H5 | 0.9300 | C25—H25 | 0.9300 |
| C6—H6 | 0.9300 | C26—N6 | 1.144 (3) |
| C7—C6 | 1.397 (3) | ||
| O1—Cd1—O2 | 54.33 (5) | C4—C5—H5 | 120.8 |
| O1—Cd1—O5 | 161.73 (6) | C6—C5—H5 | 120.8 |
| O1—Cd1—O5i | 85.39 (6) | C5—C6—C7 | 120.1 (2) |
| O1—Cd1—O6 | 144.74 (6) | C5—C6—H6 | 120.0 |
| O1—Cd1—N3 | 88.63 (6) | C7—C6—H6 | 120.0 |
| O1—Cd1—N5 | 87.92 (6) | C2—C7—C6 | 120.5 (2) |
| O1—Cd1—C1 | 27.40 (6) | C2—C7—H7 | 119.7 |
| O2—Cd1—O5 | 143.94 (5) | C6—C7—H7 | 119.7 |
| O2—Cd1—C1 | 26.95 (6) | O5—C8—C9 | 119.48 (19) |
| O5i—Cd1—O2 | 139.57 (5) | O6—C8—O5 | 122.10 (18) |
| O5i—Cd1—O5 | 76.40 (5) | O6—C8—C9 | 118.41 (18) |
| O5—Cd1—C1 | 170.87 (6) | C10—C9—C8 | 119.84 (19) |
| O5i—Cd1—C1 | 112.66 (6) | C14—C9—C8 | 120.56 (19) |
| O6—Cd1—O2 | 90.60 (5) | C14—C9—C10 | 119.60 (18) |
| O6—Cd1—O5 | 53.47 (5) | C9—C10—H10 | 121.0 |
| O6—Cd1—O5i | 129.14 (5) | C11—C10—C9 | 117.9 (2) |
| O6—Cd1—N5 | 89.46 (6) | C11—C10—H10 | 121.0 |
| O6—Cd1—C1 | 117.41 (6) | C10—C11—N2 | 118.8 (2) |
| N3—Cd1—O2 | 93.62 (6) | C12—C11—N2 | 117.92 (19) |
| N3—Cd1—O5 | 89.29 (6) | C12—C11—C10 | 123.3 (2) |
| N3—Cd1—O5i | 88.16 (6) | C11—C12—C13 | 118.0 (2) |
| N3—Cd1—O6 | 98.23 (6) | C11—C12—H12 | 121.0 |
| N3—Cd1—N5 | 170.84 (6) | C13—C12—H12 | 121.0 |
| N3—Cd1—C1 | 92.02 (6) | C12—C13—C14 | 120.3 (2) |
| N5—Cd1—O2 | 91.25 (6) | C12—C13—H13 | 119.8 |
| N5—Cd1—O5 | 91.33 (6) | C14—C13—H13 | 119.8 |
| N5—Cd1—O5i | 83.11 (6) | C9—C14—H14 | 119.6 |
| N5—Cd1—C1 | 88.81 (6) | C13—C14—C9 | 120.9 (2) |
| C1—O1—Cd1 | 95.65 (12) | C13—C14—H14 | 119.6 |
| C1—O2—Cd1 | 86.70 (13) | N3—C15—C16 | 121.9 (2) |
| Cd1i—O5—Cd1 | 103.60 (5) | N3—C15—H15 | 119.0 |
| C8—O5—Cd1i | 165.65 (15) | C16—C15—H15 | 119.0 |
| C8—O5—Cd1 | 87.27 (13) | C15—C16—C17 | 119.8 (2) |
| C8—O6—Cd1 | 97.16 (12) | C15—C16—C20 | 119.9 (2) |
| O3—N1—C4 | 118.33 (19) | C17—C16—C20 | 120.3 (2) |
| O4—N1—O3 | 123.3 (2) | C16—C17—H17 | 120.9 |
| O4—N1—C4 | 118.4 (2) | C18—C17—C16 | 118.1 (2) |
| O7—N2—O8 | 122.4 (2) | C18—C17—H17 | 120.9 |
| O7—N2—C11 | 119.0 (2) | C17—C18—H18 | 120.7 |
| O8—N2—C11 | 118.6 (2) | C19—C18—C17 | 118.7 (2) |
| C15—N3—Cd1 | 120.77 (14) | C19—C18—H18 | 120.7 |
| C15—N3—C19 | 118.26 (19) | N3—C19—C18 | 123.2 (2) |
| C19—N3—Cd1 | 120.93 (14) | N3—C19—H19 | 118.4 |
| C21—N5—Cd1 | 121.21 (14) | C18—C19—H19 | 118.4 |
| C25—N5—Cd1 | 121.09 (15) | N4—C20—C16 | 178.3 (5) |
| C25—N5—C21 | 117.68 (19) | N5—C21—C22 | 122.5 (2) |
| O1—C1—Cd1 | 56.96 (10) | N5—C21—H21 | 118.7 |
| O1—C1—C2 | 116.79 (18) | C22—C21—H21 | 118.7 |
| O2—C1—Cd1 | 66.35 (12) | C21—C22—C23 | 119.3 (2) |
| O2—C1—O1 | 123.24 (19) | C21—C22—C26 | 119.7 (2) |
| O2—C1—C2 | 120.0 (2) | C23—C22—C26 | 121.0 (2) |
| C2—C1—Cd1 | 172.89 (15) | C22—C23—H23 | 121.1 |
| C3—C2—C1 | 118.64 (19) | C24—C23—C22 | 117.9 (2) |
| C7—C2—C1 | 121.51 (19) | C24—C23—H23 | 121.1 |
| C7—C2—C3 | 119.80 (19) | C23—C24—C25 | 119.2 (2) |
| C2—C3—H3 | 120.6 | C23—C24—H24 | 120.4 |
| C4—C3—C2 | 118.7 (2) | C25—C24—H24 | 120.4 |
| C4—C3—H3 | 120.6 | N5—C25—C24 | 123.4 (2) |
| C3—C4—N1 | 118.3 (2) | N5—C25—H25 | 118.3 |
| C5—C4—N1 | 119.2 (2) | C24—C25—H25 | 118.3 |
| C5—C4—C3 | 122.4 (2) | N6—C26—C22 | 178.8 (3) |
| C4—C5—C6 | 118.5 (2) | ||
| O2—Cd1—O1—C1 | −1.60 (12) | Cd1—O1—C1—C2 | −176.08 (15) |
| O5—Cd1—O1—C1 | 179.36 (16) | Cd1—O5—C8—O6 | −0.7 (2) |
| O5i—Cd1—O1—C1 | 174.69 (14) | Cd1i—O5—C8—O6 | −140.5 (5) |
| O6—Cd1—O1—C1 | 5.3 (2) | Cd1—O5—C8—C9 | 178.05 (16) |
| N3—Cd1—O1—C1 | −97.04 (14) | Cd1i—O5—C8—C9 | 38.3 (7) |
| N5—Cd1—O1—C1 | 91.44 (14) | Cd1—O6—C8—O5 | 0.8 (2) |
| O1—Cd1—O2—C1 | 1.62 (12) | Cd1—O6—C8—C9 | −177.99 (15) |
| O5—Cd1—O2—C1 | −178.89 (11) | O3—N1—C4—C3 | −3.3 (3) |
| O5i—Cd1—O2—C1 | −4.09 (18) | O3—N1—C4—C5 | 178.5 (2) |
| O6—Cd1—O2—C1 | −174.39 (13) | O4—N1—C4—C3 | 176.7 (2) |
| N3—Cd1—O2—C1 | 87.33 (13) | O4—N1—C4—C5 | −1.5 (3) |
| N5—Cd1—O2—C1 | −84.92 (14) | Cd1—N3—C15—C16 | −178.18 (17) |
| O1—Cd1—O5—Cd1i | −4.8 (2) | C19—N3—C15—C16 | −0.7 (3) |
| O1—Cd1—O5—C8 | −175.30 (18) | Cd1—N3—C19—C18 | 177.4 (2) |
| O2—Cd1—O5—Cd1i | 176.53 (8) | C15—N3—C19—C18 | 0.0 (4) |
| O2—Cd1—O5—C8 | 6.03 (18) | Cd1—N5—C21—C22 | −178.82 (17) |
| O5i—Cd1—O5—Cd1i | 0.0 | C25—N5—C21—C22 | −0.5 (3) |
| O5i—Cd1—O5—C8 | −170.51 (16) | Cd1—N5—C25—C24 | 179.2 (2) |
| O6—Cd1—O5—Cd1i | 170.93 (10) | C21—N5—C25—C24 | 0.8 (4) |
| O6—Cd1—O5—C8 | 0.42 (12) | O1—C1—O2—Cd1 | −2.9 (2) |
| N3—Cd1—O5—Cd1i | −88.28 (7) | C2—C1—O2—Cd1 | 176.33 (17) |
| N3—Cd1—O5—C8 | 101.21 (13) | O1—C1—C2—C3 | −15.8 (3) |
| N5—Cd1—O5—Cd1i | 82.58 (7) | O1—C1—C2—C7 | 161.6 (2) |
| N5—Cd1—O5—C8 | −87.92 (13) | O2—C1—C2—C3 | 164.9 (2) |
| O1—Cd1—O6—C8 | 177.25 (12) | O2—C1—C2—C7 | −17.6 (3) |
| O2—Cd1—O6—C8 | −177.13 (13) | C1—C2—C7—C6 | −176.7 (2) |
| O5—Cd1—O6—C8 | −0.42 (12) | C3—C2—C7—C6 | 0.7 (4) |
| O5i—Cd1—O6—C8 | 10.98 (16) | C4—C3—C2—C1 | 177.69 (18) |
| N3—Cd1—O6—C8 | −83.38 (13) | C4—C3—C2—C7 | 0.2 (3) |
| N5—Cd1—O6—C8 | 91.63 (13) | C2—C3—C4—N1 | −179.25 (18) |
| C1—Cd1—O6—C8 | −179.99 (12) | C2—C3—C4—C5 | −1.1 (3) |
| O1—Cd1—N3—C15 | 146.88 (17) | N1—C4—C5—C6 | 179.1 (2) |
| O1—Cd1—N3—C19 | −30.50 (17) | C3—C4—C5—C6 | 0.9 (4) |
| O2—Cd1—N3—C15 | 92.75 (17) | C4—C5—C6—C7 | 0.1 (4) |
| O2—Cd1—N3—C19 | −84.63 (17) | C2—C7—C6—C5 | −0.9 (4) |
| O5—Cd1—N3—C15 | −51.27 (16) | O5—C8—C9—C10 | −176.4 (2) |
| O5i—Cd1—N3—C15 | −127.69 (17) | O5—C8—C9—C14 | 3.1 (3) |
| O5—Cd1—N3—C19 | 131.34 (17) | O6—C8—C9—C10 | 2.4 (3) |
| O5i—Cd1—N3—C19 | 54.93 (17) | O6—C8—C9—C14 | −178.1 (2) |
| O6—Cd1—N3—C15 | 1.62 (17) | C8—C9—C10—C11 | 178.96 (19) |
| O6—Cd1—N3—C19 | −175.77 (17) | C14—C9—C10—C11 | −0.6 (3) |
| C1—Cd1—N3—C15 | 119.69 (17) | C8—C9—C14—C13 | 179.8 (2) |
| C1—Cd1—N3—C19 | −57.69 (17) | C10—C9—C14—C13 | −0.6 (4) |
| O1—Cd1—N5—C21 | 25.91 (17) | C9—C10—C11—N2 | −179.8 (2) |
| O1—Cd1—N5—C25 | −152.4 (2) | C9—C10—C11—C12 | 1.4 (4) |
| O2—Cd1—N5—C21 | 80.15 (18) | C10—C11—N2—O7 | −7.6 (4) |
| O2—Cd1—N5—C25 | −98.16 (19) | C10—C11—N2—O8 | 173.3 (3) |
| O5—Cd1—N5—C21 | −135.83 (17) | C12—C11—N2—O7 | 171.3 (3) |
| O5—Cd1—N5—C25 | 45.86 (19) | C12—C11—N2—O8 | −7.7 (4) |
| O5i—Cd1—N5—C25 | 122.0 (2) | N2—C11—C12—C13 | −179.7 (3) |
| O5i—Cd1—N5—C21 | −59.69 (17) | C10—C11—C12—C13 | −0.9 (4) |
| O6—Cd1—N5—C25 | −7.57 (19) | C11—C12—C13—C14 | −0.4 (5) |
| O6—Cd1—N5—C21 | 170.74 (18) | C9—C14—C13—C12 | 1.2 (5) |
| C1—Cd1—N5—C21 | 53.30 (18) | N3—C15—C16—C17 | 0.9 (4) |
| C1—Cd1—N5—C25 | −125.0 (2) | N3—C15—C16—C20 | −177.6 (3) |
| O1—Cd1—C1—O2 | −177.1 (2) | C15—C16—C17—C18 | −0.2 (4) |
| O2—Cd1—C1—O1 | 177.1 (2) | C20—C16—C17—C18 | 178.2 (3) |
| O5i—Cd1—C1—O1 | −5.74 (15) | C19—C18—C17—C16 | −0.4 (4) |
| O5i—Cd1—C1—O2 | 177.13 (13) | N3—C19—C18—C17 | 0.6 (4) |
| O6—Cd1—C1—O1 | −176.54 (13) | N5—C21—C22—C23 | −0.3 (4) |
| O6—Cd1—C1—O2 | 6.33 (15) | N5—C21—C22—C26 | 178.2 (2) |
| N3—Cd1—C1—O1 | 83.11 (14) | C21—C22—C23—C24 | 0.6 (4) |
| N3—Cd1—C1—O2 | −94.02 (14) | C26—C22—C23—C24 | −177.8 (3) |
| N5—Cd1—C1—O1 | −87.76 (14) | C22—C23—C24—C25 | −0.3 (4) |
| N5—Cd1—C1—O2 | 95.10 (14) | N5—C25—C24—C23 | −0.5 (5) |
| Cd1—O1—C1—O2 | 3.1 (2) |
Symmetry code: (i) −x, −y+1, −z+1.
Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| C14—H14···O1i | 0.93 | 2.20 | 3.108 (3) | 167 |
| C15—H15···O2ii | 0.93 | 2.32 | 3.111 (3) | 143 |
| C23—H23···N4iii | 0.93 | 2.38 | 3.236 (5) | 154 |
| C25—H25···O6 | 0.93 | 2.58 | 3.242 (3) | 128 |
| C10—H10···Cg3ii | 0.93 | 3.26 | 4.186 (3) | 176 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z−1.
References
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989017002675/wm5366sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989017002675/wm5366Isup2.hkl
CCDC reference: 1533101
Additional supporting information: crystallographic information; 3D view; checkCIF report