research communications
N′-[(E)-(phenyl)(pyridin-2-yl-κN)methylidene]pyridine-2-carbohydrazide-κ2N′,O}cadmium(II)
and Hirshfeld surface analysis of diiodido{aİlke Education and Health Foundation, Cappadocia University, Cappadocia Vocational College, The Medical Imaging Techniques Program, 50420 Mustafapaşa,Ürgüp, Nevşehir, Turkey, bDepartment of Inorganic Chemistry, Faculty of Chemistry, University of Tabriz, Tabriz, Iran, cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and dLaboratorio de Estudios Cristalograficos, IACT, CSIC-Universidad de Granada, Av. De las Palmeras 4, E-18100 Armilla, Granada, Spain
*Correspondence e-mail: akkurt@erciyes.edu.tr
In each of the two independent molecules in the 2(C18H14N4O)], the N,O,N′-tridentate N′-[(E)-(phenyl)(pyridin-2-yl-κN)methylidene]pyridine-2-carbohydrazide ligand and two iodide anions form an I2N2O pentacoordination sphere, with a distorted square-pyramidal geometry, with an I atom in the apical position. Both molecules feature an intramolecular N—H⋯N hydrogen bond. In the crystal, weak aromatic π–π stacking interactions [centroid–centroid separation = 3.830 (2) Å] link the molecules into dimers.
of the title compound, [CdIKeywords: crystal structure; N′-[(E)-(pyridin-2-yl)methylidene]pyridine-2-carbohydrazide; cadmium; iodide; hydrogen bonding; Hirshfeld surface analysis.
CCDC reference: 1935658
1. Chemical context
Hydrazone ligands show high efficiency in chelating transition-metal ions (Afkhami et al., 2017a); such ligands obtained from pyridine carboxylic acids can act as ditopic ligands because of their two different donor sites, including an N-donor pyridine group and a tridentate coordination pocket, and have the potential to form mono-, di- and multinuclear structures (Afkhami et al., 2017b). In this work, we report the synthesis, and Hirshfeld surface analysis of the title CdII complex, (I), containing the tridentate hydrazone ligand N′-[(E)-(pyridin-2-yl)methylidene]pyridine-2-carbohydrazide.
2. Structural commentary
The molecular structure of (I), which contains two [CdI2(C18H14N4O)] molecules, A (with Cd1) and B (with Cd2), in the is shown in Fig. 1. In both molecules, the Cd atom is pentacoordinated to two N, one O and two I atoms (Table 1). The Addison τ parameter (Addison et al., 1984) quantifies the distinction between trigonal–bipyramidal (ideally τ = 1) and square-pyramidal (ideally τ = 0) geometries. For the title complex, τ = 0.11 for A and 0.09 for B, indicating a distorted square-pyramidal geometry (Fig. 2).
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The dihedral angles between the planes of the pyridine rings are 4.44 (17)° for A and and 15.63 (17)° for B. For A, the Cd1—I1 and Cd1—I2 bond lengths are 2.7509 (4) and 2.6917 (4) Å, respectively, and the Cd1—N2 bond length is 2.342 (3) Å. For B, the Cd2—I3 and Cd2—I4 bond lengths are 2.7530 (4) and 2.6732 (4) Å, respectively, and the Cd2—N6 bond length is 2.344 (3) Å. Both molecules feature an intramolecular N—H⋯N hydrogen bond with the pyridine-ring N atom as the acceptor (Table 2).
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3. Supramolecular features and Hirshfeld surface analysis
In the crystal of (I), molecules are linked into dimeric A + B associations by aromatic π–π stacking interactions [Cg3⋯Cg4(−x, 1 − y, 1 − z) = 3.830 (2) Å, where Cg3 and Cg4 are the centroids of the pyridine rings (N1/C1–C5) and (N4/C14–C18), respectively] (Fig. 3).
The Hirshfeld surface analysis (Spackman & Jayatilaka, 2009) of (I) was performed using CrystalExplorer3.1 (Wolff et al., 2012) to generate dnorm surface plots and two -dimensional fingerprint plots (Spackman & McKinnon, 2002). Fig. 4a shows the overall two-dimensional fingerprint plot for the contacts contributing to the Hirshfeld surface. The percentage contributions and Hirshfeld surfaces for H⋯I /I⋯H contacts (30.5%), H⋯H (29.5%), C⋯H / H⋯C (13.3%), H⋯O / O⋯H (5.6%) and C⋯I / I⋯C (4.9%) are shown in Figs. 4b–f, respectively. The full list of percentage surface contributions in given in Table 3.
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4. Database survey
All bond lengths and angles in (I) fall within their expected ranges and are comparable with those reported for related structures, such as bis{N′-[(E)-4-hydroxybenzylidene]-pyridine-4-carbohydrazide-κN1}diiodidocadmium methanol disolvate (CCDC refcode: DADHIC; Afkhami et al., 2017c), dibromido{N′-[1-(pyridin-2-yl)ethylidene]picolinohydrazide-κ2N′,O}cadmium (ACUDOT;Akkurt et al., 2012), di-μ-chlorido-bis(chlorido{N′-[phenyl(pyridin-2-yl-κN)methylidene]pyridine-2-carbohydrazide-κ2N′,O}cadmium) (JOBTEB; Akkurt et al., 2014), bis{2-[(2,4-dimethylphenyl)iminomethyl]pyridine-κ2N,N′}bis(thiocyanato-κN)cadmium (GARTAW; Malekshahian et al., 2012) and cis-diaquabis-[(E)-4-(2-hydroxybenzylideneamino)benzoato-κ2O,O′]cadmium (WEHSOS; Yao et al., 2006) in which layers are built by strong O—H⋯O hydrogen bonds. In the crystal of diiodido-{N-[(pyridin-2-yl-κN)methylidene]picolinohydrazide-κ2N′,O}cadmium (WASCEB; Khandar et al., 2017), the molecules are linked by N—H⋯I hydrogen bonds, forming chains propagating along [010].
5. Synthesis and crystallization
The N′-[(E)-(pyridin-2-yl)methylidene]pyridine-2-carbohydrazide ligand was synthesized according to the literature method (Abedi et al., 2016). To prepare single crystals of (I), an equimolar mixture (1.0 mmol) of the hydrazone ligand and metal salt [CdI2] were placed in the main arm of a branched tube, and methanol was carefully added to fill the arms (Khandar et al., 2015). The tube was sealed and the mixture-containing arm was immersed in an oil bath at 333 K while the branched arm was kept at room temperature. After a couple of days, yellow prisms of (I) had been deposited in the cooler arm and these were isolated, filtered off, washed with diethyl ether and dried over P4O10 in vacuo.
6. Refinement
Crystal data, data collection and structure . H atoms were placed in calculated positions (C—H = 0.95 Å, N—H= 0.88 Å) and included in the in the riding-model approximation, with Uiso(H) = 1.2Ueq(N,C).
details are summarized in Table 4Supporting information
CCDC reference: 1935658
https://doi.org/10.1107/S2056989019008831/hb7823sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019008831/hb7823Isup2.hkl
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2015).[CdI2(C18H14N4O)] | F(000) = 2496 |
Mr = 668.53 | Dx = 2.200 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 19.9158 (15) Å | Cell parameters from 9930 reflections |
b = 11.7252 (9) Å | θ = 2.2–27.8° |
c = 17.8349 (14) Å | µ = 4.16 mm−1 |
β = 104.207 (1)° | T = 100 K |
V = 4037.4 (5) Å3 | Hexagonal prism, yellow |
Z = 8 | 0.34 × 0.33 × 0.17 mm |
Bruker SMART APEX diffractometer | 7948 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
φ and ω scans | θmax = 28.2°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −26→25 |
Tmin = 0.600, Tmax = 0.746 | k = −15→12 |
24216 measured reflections | l = −20→22 |
9018 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.027 | H-atom parameters constrained |
wR(F2) = 0.064 | w = 1/[σ2(Fo2) + (0.0306P)2 + 5.7109P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
9018 reflections | Δρmax = 1.26 e Å−3 |
469 parameters | Δρmin = −0.56 e Å−3 |
0 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | −0.15988 (18) | 0.7689 (3) | 0.5679 (2) | 0.0265 (8) | |
H1 | −0.200797 | 0.761245 | 0.527529 | 0.032* | |
C2 | −0.1651 (2) | 0.8147 (3) | 0.6379 (2) | 0.0296 (8) | |
H2 | −0.208603 | 0.839406 | 0.644720 | 0.036* | |
C3 | −0.1066 (2) | 0.8238 (3) | 0.6971 (2) | 0.0295 (8) | |
H3A | −0.108958 | 0.855873 | 0.745277 | 0.035* | |
C4 | −0.04377 (18) | 0.7855 (3) | 0.6858 (2) | 0.0245 (7) | |
H4 | −0.002709 | 0.789869 | 0.726250 | 0.029* | |
C5 | −0.04221 (17) | 0.7409 (3) | 0.6145 (2) | 0.0218 (7) | |
C6 | 0.02285 (17) | 0.6967 (3) | 0.59802 (19) | 0.0205 (7) | |
C7 | 0.08845 (17) | 0.6963 (3) | 0.65920 (19) | 0.0210 (7) | |
C8 | 0.09709 (19) | 0.6246 (3) | 0.7225 (2) | 0.0292 (8) | |
H8 | 0.060605 | 0.575262 | 0.727562 | 0.035* | |
C9 | 0.1594 (2) | 0.6251 (4) | 0.7788 (2) | 0.0352 (9) | |
H9 | 0.165419 | 0.575842 | 0.822230 | 0.042* | |
C10 | 0.2129 (2) | 0.6974 (4) | 0.7716 (2) | 0.0342 (9) | |
H10 | 0.255585 | 0.697081 | 0.809828 | 0.041* | |
C11 | 0.2035 (2) | 0.7697 (4) | 0.7086 (2) | 0.0339 (9) | |
H11 | 0.239690 | 0.820040 | 0.703963 | 0.041* | |
C12 | 0.1420 (2) | 0.7691 (3) | 0.6523 (2) | 0.0306 (8) | |
H12 | 0.136162 | 0.818266 | 0.608864 | 0.037* | |
C13 | 0.06053 (17) | 0.5883 (3) | 0.4289 (2) | 0.0214 (7) | |
C14 | 0.12412 (17) | 0.5528 (3) | 0.4049 (2) | 0.0216 (7) | |
C15 | 0.11899 (18) | 0.5094 (3) | 0.3316 (2) | 0.0242 (7) | |
H15 | 0.075311 | 0.501950 | 0.295562 | 0.029* | |
C16 | 0.17994 (19) | 0.4772 (3) | 0.3122 (2) | 0.0283 (8) | |
H16 | 0.178904 | 0.447717 | 0.262261 | 0.034* | |
C17 | 0.24142 (18) | 0.4888 (3) | 0.3667 (2) | 0.0304 (8) | |
H17 | 0.283676 | 0.466404 | 0.355316 | 0.036* | |
C18 | 0.24135 (18) | 0.5336 (3) | 0.4386 (2) | 0.0279 (8) | |
H18 | 0.284391 | 0.541529 | 0.475719 | 0.033* | |
Cd1 | −0.08166 (2) | 0.70487 (2) | 0.42925 (2) | 0.02325 (6) | |
I1 | −0.02803 (2) | 0.89997 (2) | 0.38096 (2) | 0.02834 (6) | |
I2 | −0.20450 (2) | 0.60932 (2) | 0.36168 (2) | 0.03106 (7) | |
N1 | −0.09966 (14) | 0.7350 (3) | 0.55485 (17) | 0.0232 (6) | |
N2 | 0.01685 (14) | 0.6622 (2) | 0.52758 (16) | 0.0215 (6) | |
N3 | 0.07222 (14) | 0.6208 (3) | 0.50403 (16) | 0.0226 (6) | |
H3 | 0.113503 | 0.615314 | 0.535951 | 0.027* | |
N4 | 0.18386 (15) | 0.5661 (3) | 0.45830 (18) | 0.0253 (6) | |
O1 | 0.00248 (12) | 0.5878 (2) | 0.38410 (14) | 0.0256 (5) | |
C19 | 0.47181 (19) | 0.5871 (3) | 0.5866 (2) | 0.0270 (8) | |
H19 | 0.511452 | 0.549614 | 0.577806 | 0.032* | |
C20 | 0.4403 (2) | 0.5409 (3) | 0.6405 (2) | 0.0314 (8) | |
H20 | 0.457550 | 0.472829 | 0.667323 | 0.038* | |
C21 | 0.3830 (2) | 0.5955 (3) | 0.6547 (2) | 0.0303 (8) | |
H21 | 0.359945 | 0.565392 | 0.691081 | 0.036* | |
C22 | 0.36007 (19) | 0.6954 (3) | 0.6145 (2) | 0.0261 (7) | |
H22 | 0.321326 | 0.735372 | 0.623582 | 0.031* | |
C23 | 0.39437 (17) | 0.7359 (3) | 0.5611 (2) | 0.0224 (7) | |
C24 | 0.37348 (17) | 0.8435 (3) | 0.5184 (2) | 0.0225 (7) | |
C25 | 0.30874 (18) | 0.9009 (3) | 0.5247 (2) | 0.0255 (8) | |
C26 | 0.3113 (2) | 0.9956 (4) | 0.5723 (3) | 0.0385 (10) | |
H26 | 0.354632 | 1.025469 | 0.599897 | 0.046* | |
C27 | 0.2505 (3) | 1.0457 (4) | 0.5790 (3) | 0.0543 (13) | |
H27 | 0.251823 | 1.110396 | 0.611406 | 0.065* | |
C28 | 0.1876 (3) | 1.0018 (4) | 0.5387 (3) | 0.0526 (14) | |
H28 | 0.145841 | 1.036347 | 0.544022 | 0.063* | |
C29 | 0.1845 (2) | 0.9088 (4) | 0.4909 (3) | 0.0438 (11) | |
H29 | 0.140978 | 0.879841 | 0.462879 | 0.053* | |
C30 | 0.2457 (2) | 0.8577 (4) | 0.4840 (3) | 0.0350 (9) | |
H30 | 0.244173 | 0.793135 | 0.451413 | 0.042* | |
C31 | 0.43945 (18) | 1.0017 (3) | 0.3850 (2) | 0.0245 (7) | |
C32 | 0.41803 (18) | 1.1068 (3) | 0.3382 (2) | 0.0238 (7) | |
C33 | 0.4640 (2) | 1.1575 (3) | 0.3007 (2) | 0.0269 (8) | |
H33 | 0.508151 | 1.124917 | 0.303051 | 0.032* | |
C34 | 0.4431 (2) | 1.2568 (3) | 0.2598 (2) | 0.0307 (8) | |
H34 | 0.472542 | 1.294272 | 0.233131 | 0.037* | |
C35 | 0.3784 (2) | 1.3003 (3) | 0.2587 (2) | 0.0304 (8) | |
H35 | 0.363169 | 1.369376 | 0.232195 | 0.036* | |
C36 | 0.3361 (2) | 1.2419 (3) | 0.2967 (2) | 0.0294 (8) | |
H36 | 0.291160 | 1.271413 | 0.293948 | 0.035* | |
Cd2 | 0.49190 (2) | 0.75304 (2) | 0.44240 (2) | 0.02348 (6) | |
I3 | 0.39729 (2) | 0.65574 (2) | 0.32031 (2) | 0.02644 (6) | |
I4 | 0.62809 (2) | 0.71202 (2) | 0.47863 (2) | 0.03079 (7) | |
N5 | 0.44979 (15) | 0.6813 (3) | 0.54638 (17) | 0.0241 (6) | |
N6 | 0.41289 (15) | 0.8790 (2) | 0.47642 (17) | 0.0233 (6) | |
N7 | 0.39722 (15) | 0.9746 (2) | 0.43223 (17) | 0.0246 (6) | |
H7 | 0.361299 | 1.017289 | 0.434038 | 0.030* | |
N8 | 0.35512 (15) | 1.1468 (3) | 0.33692 (18) | 0.0266 (6) | |
O2 | 0.49091 (13) | 0.9444 (2) | 0.38286 (15) | 0.0294 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0237 (17) | 0.030 (2) | 0.0272 (19) | 0.0041 (15) | 0.0095 (15) | 0.0072 (15) |
C2 | 0.0316 (19) | 0.033 (2) | 0.029 (2) | 0.0070 (16) | 0.0171 (16) | 0.0084 (16) |
C3 | 0.041 (2) | 0.030 (2) | 0.0241 (19) | 0.0062 (16) | 0.0192 (17) | 0.0042 (15) |
C4 | 0.0274 (17) | 0.0256 (19) | 0.0219 (18) | 0.0009 (14) | 0.0085 (14) | 0.0011 (14) |
C5 | 0.0210 (16) | 0.0223 (17) | 0.0244 (18) | −0.0003 (13) | 0.0101 (14) | 0.0030 (14) |
C6 | 0.0209 (16) | 0.0217 (17) | 0.0199 (17) | −0.0009 (13) | 0.0066 (13) | −0.0004 (13) |
C7 | 0.0193 (15) | 0.0247 (18) | 0.0190 (16) | −0.0002 (13) | 0.0049 (13) | −0.0033 (13) |
C8 | 0.0287 (18) | 0.029 (2) | 0.029 (2) | −0.0017 (15) | 0.0043 (15) | 0.0055 (15) |
C9 | 0.035 (2) | 0.036 (2) | 0.030 (2) | −0.0039 (17) | −0.0013 (17) | 0.0058 (17) |
C10 | 0.0255 (18) | 0.042 (2) | 0.032 (2) | −0.0019 (17) | 0.0016 (16) | −0.0077 (18) |
C11 | 0.0280 (19) | 0.042 (2) | 0.035 (2) | −0.0105 (17) | 0.0130 (17) | −0.0033 (18) |
C12 | 0.034 (2) | 0.036 (2) | 0.0242 (19) | −0.0050 (17) | 0.0111 (16) | 0.0030 (16) |
C13 | 0.0248 (17) | 0.0197 (17) | 0.0212 (17) | 0.0010 (13) | 0.0084 (14) | 0.0022 (13) |
C14 | 0.0220 (16) | 0.0196 (17) | 0.0241 (18) | 0.0013 (13) | 0.0075 (14) | 0.0027 (13) |
C15 | 0.0246 (17) | 0.0250 (18) | 0.0234 (18) | −0.0014 (14) | 0.0069 (14) | 0.0001 (14) |
C16 | 0.0298 (18) | 0.028 (2) | 0.031 (2) | 0.0020 (15) | 0.0164 (16) | 0.0002 (16) |
C17 | 0.0232 (17) | 0.028 (2) | 0.043 (2) | 0.0032 (15) | 0.0142 (16) | −0.0020 (17) |
C18 | 0.0197 (16) | 0.0265 (19) | 0.037 (2) | −0.0008 (14) | 0.0063 (15) | −0.0052 (16) |
Cd1 | 0.01973 (12) | 0.03217 (15) | 0.01853 (13) | 0.00340 (10) | 0.00597 (10) | 0.00226 (10) |
I1 | 0.02828 (12) | 0.03337 (14) | 0.02603 (13) | 0.00073 (10) | 0.01178 (10) | 0.00283 (10) |
I2 | 0.02091 (11) | 0.04454 (16) | 0.02837 (13) | −0.00209 (10) | 0.00728 (9) | −0.00054 (11) |
N1 | 0.0219 (14) | 0.0293 (16) | 0.0201 (15) | 0.0026 (12) | 0.0087 (12) | 0.0045 (12) |
N2 | 0.0196 (13) | 0.0252 (15) | 0.0218 (15) | 0.0054 (11) | 0.0087 (11) | 0.0014 (12) |
N3 | 0.0195 (13) | 0.0299 (16) | 0.0186 (14) | 0.0059 (12) | 0.0052 (11) | −0.0005 (12) |
N4 | 0.0235 (14) | 0.0240 (15) | 0.0282 (16) | 0.0021 (12) | 0.0056 (12) | −0.0024 (12) |
O1 | 0.0227 (12) | 0.0337 (14) | 0.0206 (12) | 0.0040 (10) | 0.0057 (10) | −0.0023 (10) |
C19 | 0.0298 (18) | 0.0232 (18) | 0.0265 (19) | 0.0055 (15) | 0.0038 (15) | 0.0003 (14) |
C20 | 0.044 (2) | 0.029 (2) | 0.0211 (18) | 0.0063 (17) | 0.0077 (16) | 0.0018 (15) |
C21 | 0.041 (2) | 0.030 (2) | 0.0222 (19) | 0.0011 (16) | 0.0106 (16) | 0.0025 (15) |
C22 | 0.0300 (18) | 0.0263 (19) | 0.0239 (18) | 0.0039 (15) | 0.0100 (15) | 0.0004 (15) |
C23 | 0.0252 (17) | 0.0218 (17) | 0.0198 (17) | 0.0017 (14) | 0.0046 (14) | −0.0012 (13) |
C24 | 0.0243 (16) | 0.0219 (17) | 0.0219 (17) | 0.0028 (14) | 0.0067 (14) | −0.0026 (14) |
C25 | 0.0300 (18) | 0.0250 (19) | 0.0268 (19) | 0.0060 (14) | 0.0172 (15) | 0.0085 (14) |
C26 | 0.047 (2) | 0.031 (2) | 0.042 (2) | 0.0089 (18) | 0.019 (2) | −0.0008 (18) |
C27 | 0.073 (3) | 0.042 (3) | 0.061 (3) | 0.023 (3) | 0.042 (3) | 0.004 (2) |
C28 | 0.052 (3) | 0.046 (3) | 0.075 (4) | 0.025 (2) | 0.045 (3) | 0.033 (3) |
C29 | 0.027 (2) | 0.048 (3) | 0.059 (3) | 0.0041 (18) | 0.017 (2) | 0.027 (2) |
C30 | 0.0312 (19) | 0.034 (2) | 0.044 (2) | 0.0024 (17) | 0.0165 (18) | 0.0093 (18) |
C31 | 0.0306 (18) | 0.0219 (18) | 0.0230 (18) | −0.0023 (14) | 0.0102 (15) | −0.0020 (14) |
C32 | 0.0310 (18) | 0.0215 (18) | 0.0196 (17) | −0.0063 (14) | 0.0076 (14) | −0.0062 (13) |
C33 | 0.0352 (19) | 0.0255 (19) | 0.0213 (18) | −0.0065 (15) | 0.0098 (15) | −0.0066 (14) |
C34 | 0.043 (2) | 0.027 (2) | 0.0218 (19) | −0.0086 (17) | 0.0082 (16) | −0.0013 (15) |
C35 | 0.042 (2) | 0.0246 (19) | 0.0251 (19) | 0.0006 (16) | 0.0099 (17) | 0.0026 (15) |
C36 | 0.0334 (19) | 0.0263 (19) | 0.029 (2) | 0.0031 (15) | 0.0077 (16) | 0.0028 (15) |
Cd2 | 0.02161 (12) | 0.02587 (14) | 0.02434 (13) | 0.00368 (10) | 0.00830 (10) | −0.00026 (10) |
I3 | 0.01929 (11) | 0.03300 (13) | 0.02632 (12) | 0.00173 (9) | 0.00425 (9) | 0.00129 (10) |
I4 | 0.02047 (11) | 0.03842 (15) | 0.03207 (14) | 0.00249 (10) | 0.00375 (10) | −0.00371 (10) |
N5 | 0.0261 (15) | 0.0262 (16) | 0.0203 (15) | 0.0034 (12) | 0.0061 (12) | 0.0000 (12) |
N6 | 0.0266 (15) | 0.0211 (15) | 0.0233 (15) | 0.0016 (12) | 0.0086 (12) | 0.0016 (12) |
N7 | 0.0315 (15) | 0.0195 (15) | 0.0266 (16) | 0.0056 (12) | 0.0143 (13) | 0.0052 (12) |
N8 | 0.0280 (15) | 0.0262 (16) | 0.0277 (16) | −0.0005 (13) | 0.0107 (13) | −0.0019 (13) |
O2 | 0.0292 (13) | 0.0266 (14) | 0.0361 (15) | 0.0038 (11) | 0.0152 (11) | 0.0024 (11) |
C1—N1 | 1.337 (4) | C19—N5 | 1.331 (5) |
C1—C2 | 1.385 (5) | C19—C20 | 1.382 (5) |
C1—H1 | 0.9500 | C19—H19 | 0.9500 |
C2—C3 | 1.371 (5) | C20—C21 | 1.384 (5) |
C2—H2 | 0.9500 | C20—H20 | 0.9500 |
C3—C4 | 1.389 (5) | C21—C22 | 1.391 (5) |
C3—H3A | 0.9500 | C21—H21 | 0.9500 |
C4—C5 | 1.381 (5) | C22—C23 | 1.385 (5) |
C4—H4 | 0.9500 | C22—H22 | 0.9500 |
C5—N1 | 1.360 (4) | C23—N5 | 1.356 (4) |
C5—C6 | 1.491 (5) | C23—C24 | 1.480 (5) |
C6—N2 | 1.297 (4) | C24—N6 | 1.280 (5) |
C6—C7 | 1.482 (4) | C24—C25 | 1.483 (5) |
C7—C8 | 1.385 (5) | C25—C30 | 1.383 (5) |
C7—C12 | 1.395 (5) | C25—C26 | 1.391 (6) |
C8—C9 | 1.391 (5) | C26—C27 | 1.377 (6) |
C8—H8 | 0.9500 | C26—H26 | 0.9500 |
C9—C10 | 1.392 (6) | C27—C28 | 1.382 (8) |
C9—H9 | 0.9500 | C27—H27 | 0.9500 |
C10—C11 | 1.385 (6) | C28—C29 | 1.376 (7) |
C10—H10 | 0.9500 | C28—H28 | 0.9500 |
C11—C12 | 1.380 (5) | C29—C30 | 1.391 (6) |
C11—H11 | 0.9500 | C29—H29 | 0.9500 |
C12—H12 | 0.9500 | C30—H30 | 0.9500 |
C13—O1 | 1.233 (4) | C31—O2 | 1.234 (4) |
C13—N3 | 1.357 (4) | C31—N7 | 1.366 (4) |
C13—C14 | 1.492 (5) | C31—C32 | 1.491 (5) |
C14—N4 | 1.338 (4) | C32—N8 | 1.332 (5) |
C14—C15 | 1.384 (5) | C32—C33 | 1.393 (5) |
C15—C16 | 1.394 (5) | C33—C34 | 1.382 (5) |
C15—H15 | 0.9500 | C33—H33 | 0.9500 |
C16—C17 | 1.371 (5) | C34—C35 | 1.380 (6) |
C16—H16 | 0.9500 | C34—H34 | 0.9500 |
C17—C18 | 1.387 (5) | C35—C36 | 1.385 (5) |
C17—H17 | 0.9500 | C35—H35 | 0.9500 |
C18—N4 | 1.333 (4) | C36—N8 | 1.330 (5) |
C18—H18 | 0.9500 | C36—H36 | 0.9500 |
Cd1—N2 | 2.342 (3) | Cd2—N6 | 2.344 (3) |
Cd1—N1 | 2.380 (3) | Cd2—N5 | 2.369 (3) |
Cd1—O1 | 2.450 (2) | Cd2—O2 | 2.481 (3) |
Cd1—I2 | 2.6917 (4) | Cd2—I4 | 2.6732 (4) |
Cd1—I1 | 2.7509 (4) | Cd2—I3 | 2.7530 (4) |
N2—N3 | 1.362 (4) | N6—N7 | 1.362 (4) |
N3—H3 | 0.8800 | N7—H7 | 0.8800 |
N1—C1—C2 | 122.7 (3) | N5—C19—C20 | 123.7 (3) |
N1—C1—H1 | 118.6 | N5—C19—H19 | 118.1 |
C2—C1—H1 | 118.6 | C20—C19—H19 | 118.1 |
C3—C2—C1 | 119.1 (3) | C19—C20—C21 | 118.8 (4) |
C3—C2—H2 | 120.4 | C19—C20—H20 | 120.6 |
C1—C2—H2 | 120.4 | C21—C20—H20 | 120.6 |
C2—C3—C4 | 119.2 (3) | C20—C21—C22 | 118.5 (4) |
C2—C3—H3A | 120.4 | C20—C21—H21 | 120.8 |
C4—C3—H3A | 120.4 | C22—C21—H21 | 120.8 |
C5—C4—C3 | 118.7 (3) | C23—C22—C21 | 119.2 (3) |
C5—C4—H4 | 120.7 | C23—C22—H22 | 120.4 |
C3—C4—H4 | 120.7 | C21—C22—H22 | 120.4 |
N1—C5—C4 | 122.3 (3) | N5—C23—C22 | 122.3 (3) |
N1—C5—C6 | 115.6 (3) | N5—C23—C24 | 116.2 (3) |
C4—C5—C6 | 122.0 (3) | C22—C23—C24 | 121.5 (3) |
N2—C6—C7 | 124.6 (3) | N6—C24—C23 | 116.3 (3) |
N2—C6—C5 | 115.0 (3) | N6—C24—C25 | 124.4 (3) |
C7—C6—C5 | 120.5 (3) | C23—C24—C25 | 119.2 (3) |
C8—C7—C12 | 119.9 (3) | C30—C25—C26 | 120.3 (4) |
C8—C7—C6 | 120.8 (3) | C30—C25—C24 | 119.2 (3) |
C12—C7—C6 | 119.3 (3) | C26—C25—C24 | 120.4 (4) |
C7—C8—C9 | 119.7 (4) | C27—C26—C25 | 119.5 (4) |
C7—C8—H8 | 120.1 | C27—C26—H26 | 120.2 |
C9—C8—H8 | 120.1 | C25—C26—H26 | 120.2 |
C8—C9—C10 | 120.3 (4) | C26—C27—C28 | 120.0 (5) |
C8—C9—H9 | 119.9 | C26—C27—H27 | 120.0 |
C10—C9—H9 | 119.9 | C28—C27—H27 | 120.0 |
C11—C10—C9 | 119.6 (4) | C29—C28—C27 | 121.0 (4) |
C11—C10—H10 | 120.2 | C29—C28—H28 | 119.5 |
C9—C10—H10 | 120.2 | C27—C28—H28 | 119.5 |
C12—C11—C10 | 120.4 (4) | C28—C29—C30 | 119.3 (4) |
C12—C11—H11 | 119.8 | C28—C29—H29 | 120.4 |
C10—C11—H11 | 119.8 | C30—C29—H29 | 120.4 |
C11—C12—C7 | 120.1 (4) | C25—C30—C29 | 119.9 (4) |
C11—C12—H12 | 120.0 | C25—C30—H30 | 120.1 |
C7—C12—H12 | 120.0 | C29—C30—H30 | 120.1 |
O1—C13—N3 | 123.2 (3) | O2—C31—N7 | 122.3 (3) |
O1—C13—C14 | 122.7 (3) | O2—C31—C32 | 124.0 (3) |
N3—C13—C14 | 114.1 (3) | N7—C31—C32 | 113.7 (3) |
N4—C14—C15 | 124.2 (3) | N8—C32—C33 | 124.6 (3) |
N4—C14—C13 | 115.7 (3) | N8—C32—C31 | 116.0 (3) |
C15—C14—C13 | 120.2 (3) | C33—C32—C31 | 119.3 (3) |
C14—C15—C16 | 117.9 (3) | C34—C33—C32 | 117.6 (4) |
C14—C15—H15 | 121.1 | C34—C33—H33 | 121.2 |
C16—C15—H15 | 121.1 | C32—C33—H33 | 121.2 |
C17—C16—C15 | 118.5 (3) | C35—C34—C33 | 118.6 (4) |
C17—C16—H16 | 120.7 | C35—C34—H34 | 120.7 |
C15—C16—H16 | 120.7 | C33—C34—H34 | 120.7 |
C16—C17—C18 | 119.4 (3) | C34—C35—C36 | 119.2 (4) |
C16—C17—H17 | 120.3 | C34—C35—H35 | 120.4 |
C18—C17—H17 | 120.3 | C36—C35—H35 | 120.4 |
N4—C18—C17 | 123.2 (3) | N8—C36—C35 | 123.5 (4) |
N4—C18—H18 | 118.4 | N8—C36—H36 | 118.3 |
C17—C18—H18 | 118.4 | C35—C36—H36 | 118.3 |
N2—Cd1—N1 | 67.60 (9) | N6—Cd2—N5 | 68.41 (10) |
N2—Cd1—O1 | 67.15 (9) | N6—Cd2—O2 | 66.77 (9) |
N1—Cd1—O1 | 131.72 (9) | N5—Cd2—O2 | 133.56 (9) |
N2—Cd1—I2 | 138.47 (7) | N6—Cd2—I4 | 139.16 (7) |
N1—Cd1—I2 | 98.79 (7) | N5—Cd2—I4 | 106.26 (7) |
O1—Cd1—I2 | 103.85 (6) | O2—Cd2—I4 | 99.62 (6) |
N2—Cd1—I1 | 95.38 (7) | N6—Cd2—I3 | 95.35 (7) |
N1—Cd1—I1 | 109.34 (7) | N5—Cd2—I3 | 99.61 (7) |
O1—Cd1—I1 | 90.77 (6) | O2—Cd2—I3 | 95.99 (6) |
I2—Cd1—I1 | 125.873 (12) | I4—Cd2—I3 | 124.998 (12) |
C1—N1—C5 | 117.8 (3) | C19—N5—C23 | 117.6 (3) |
C1—N1—Cd1 | 123.8 (2) | C19—N5—Cd2 | 125.7 (2) |
C5—N1—Cd1 | 116.9 (2) | C23—N5—Cd2 | 116.4 (2) |
C6—N2—N3 | 121.4 (3) | C24—N6—N7 | 121.4 (3) |
C6—N2—Cd1 | 121.3 (2) | C24—N6—Cd2 | 119.5 (2) |
N3—N2—Cd1 | 116.0 (2) | N7—N6—Cd2 | 116.2 (2) |
C13—N3—N2 | 116.7 (3) | N6—N7—C31 | 117.4 (3) |
C13—N3—H3 | 121.7 | N6—N7—H7 | 121.3 |
N2—N3—H3 | 121.7 | C31—N7—H7 | 121.3 |
C18—N4—C14 | 116.8 (3) | C36—N8—C32 | 116.5 (3) |
C13—O1—Cd1 | 113.1 (2) | C31—O2—Cd2 | 113.5 (2) |
N1—C1—C2—C3 | −1.4 (6) | N5—C19—C20—C21 | −0.9 (6) |
C1—C2—C3—C4 | −0.9 (6) | C19—C20—C21—C22 | −0.6 (6) |
C2—C3—C4—C5 | 1.0 (5) | C20—C21—C22—C23 | 0.9 (6) |
C3—C4—C5—N1 | 1.1 (5) | C21—C22—C23—N5 | 0.1 (5) |
C3—C4—C5—C6 | −179.2 (3) | C21—C22—C23—C24 | −178.2 (3) |
N1—C5—C6—N2 | 2.6 (4) | N5—C23—C24—N6 | −5.3 (5) |
C4—C5—C6—N2 | −177.1 (3) | C22—C23—C24—N6 | 173.1 (3) |
N1—C5—C6—C7 | −178.6 (3) | N5—C23—C24—C25 | 173.1 (3) |
C4—C5—C6—C7 | 1.7 (5) | C22—C23—C24—C25 | −8.5 (5) |
N2—C6—C7—C8 | −112.8 (4) | N6—C24—C25—C30 | 101.6 (4) |
C5—C6—C7—C8 | 68.6 (5) | C23—C24—C25—C30 | −76.6 (4) |
N2—C6—C7—C12 | 67.0 (5) | N6—C24—C25—C26 | −79.8 (5) |
C5—C6—C7—C12 | −111.7 (4) | C23—C24—C25—C26 | 101.9 (4) |
C12—C7—C8—C9 | −0.4 (6) | C30—C25—C26—C27 | 0.4 (6) |
C6—C7—C8—C9 | 179.4 (4) | C24—C25—C26—C27 | −178.1 (4) |
C7—C8—C9—C10 | 0.1 (6) | C25—C26—C27—C28 | 0.0 (7) |
C8—C9—C10—C11 | 0.6 (6) | C26—C27—C28—C29 | −0.6 (7) |
C9—C10—C11—C12 | −1.0 (6) | C27—C28—C29—C30 | 0.8 (7) |
C10—C11—C12—C7 | 0.8 (6) | C26—C25—C30—C29 | −0.2 (6) |
C8—C7—C12—C11 | −0.1 (6) | C24—C25—C30—C29 | 178.3 (4) |
C6—C7—C12—C11 | −179.8 (3) | C28—C29—C30—C25 | −0.4 (6) |
O1—C13—C14—N4 | 175.1 (3) | O2—C31—C32—N8 | 168.5 (3) |
N3—C13—C14—N4 | −5.0 (4) | N7—C31—C32—N8 | −12.5 (5) |
O1—C13—C14—C15 | −4.8 (5) | O2—C31—C32—C33 | −12.7 (5) |
N3—C13—C14—C15 | 175.1 (3) | N7—C31—C32—C33 | 166.3 (3) |
N4—C14—C15—C16 | 0.3 (5) | N8—C32—C33—C34 | 0.7 (5) |
C13—C14—C15—C16 | −179.8 (3) | C31—C32—C33—C34 | −178.0 (3) |
C14—C15—C16—C17 | 0.7 (5) | C32—C33—C34—C35 | 0.2 (5) |
C15—C16—C17—C18 | −0.9 (6) | C33—C34—C35—C36 | −1.6 (6) |
C16—C17—C18—N4 | 0.3 (6) | C34—C35—C36—N8 | 2.2 (6) |
C2—C1—N1—C5 | 3.4 (5) | C20—C19—N5—C23 | 1.9 (5) |
C2—C1—N1—Cd1 | −162.4 (3) | C20—C19—N5—Cd2 | −171.9 (3) |
C4—C5—N1—C1 | −3.3 (5) | C22—C23—N5—C19 | −1.5 (5) |
C6—C5—N1—C1 | 177.1 (3) | C24—C23—N5—C19 | 176.9 (3) |
C4—C5—N1—Cd1 | 163.5 (3) | C22—C23—N5—Cd2 | 172.8 (3) |
C6—C5—N1—Cd1 | −16.2 (4) | C24—C23—N5—Cd2 | −8.8 (4) |
C7—C6—N2—N3 | 0.6 (5) | C23—C24—N6—N7 | 177.4 (3) |
C5—C6—N2—N3 | 179.3 (3) | C25—C24—N6—N7 | −0.9 (5) |
C7—C6—N2—Cd1 | −165.7 (3) | C23—C24—N6—Cd2 | 17.4 (4) |
C5—C6—N2—Cd1 | 13.0 (4) | C25—C24—N6—Cd2 | −160.9 (3) |
O1—C13—N3—N2 | −4.9 (5) | C24—N6—N7—C31 | −175.4 (3) |
C14—C13—N3—N2 | 175.2 (3) | Cd2—N6—N7—C31 | −14.7 (4) |
C6—N2—N3—C13 | −179.2 (3) | O2—C31—N7—N6 | −1.6 (5) |
Cd1—N2—N3—C13 | −12.2 (4) | C32—C31—N7—N6 | 179.4 (3) |
C17—C18—N4—C14 | 0.6 (5) | C35—C36—N8—C32 | −1.3 (6) |
C15—C14—N4—C18 | −0.9 (5) | C33—C32—N8—C36 | −0.2 (5) |
C13—C14—N4—C18 | 179.1 (3) | C31—C32—N8—C36 | 178.6 (3) |
N3—C13—O1—Cd1 | 18.3 (4) | N7—C31—O2—Cd2 | 15.8 (4) |
C14—C13—O1—Cd1 | −161.9 (3) | C32—C31—O2—Cd2 | −165.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···N4 | 0.88 | 2.27 | 2.629 (4) | 104 |
N7—H7···N8 | 0.88 | 2.28 | 2.640 (4) | 104 |
Contact | Percentage contribution |
H···I/I···H | 30.5 |
H···H | 29.5 |
C···H/H···C | 13.3 |
H···O/O···H | 5.6 |
C···I/I···C | 4.9 |
C···C | 3.3 |
N···H/H···N | 2.9 |
C···N/N···C | 2.8 |
H···Cd/Cd···H | 2.1 |
N···I/I···N | 1.7 |
N···O/O···N | 1.5 |
I···I | 0.6 |
N···N | 0.4 |
C···O/O···C | 0.4 |
C···Cd/Cd···C | 0.3 |
N···Cd/Cd···N | 0.2 |
Acknowledgements
FAA and AAK thank the University of Tabriz for the financial support of this research.
References
Abedi, M., Yeşilel, O. Z., Mahmoudi, G., Bauzá, A., Lofland, S. E., Yerli, Y., Kaminsky, W., Garczarek, P., Zaręba, J. K., Ienco, A., Frontera, A. & Gargari, M. S. (2016). Inorg. Chim. Acta, 443, 101–109. CSD CrossRef CAS Google Scholar
Addison, A. W., Rao, T. N., Reedijk, J., van Rijn, J. & Verschoor, G. C. (1984). J. Chem. Soc. Dalton Trans. pp. 1349–1356. CSD CrossRef Web of Science Google Scholar
Afkhami, F. A., Khandar, A. A., Mahmoudi, G., Maniukiewicz, W., Gurbanov, A. V., Zubkov, F. I., Şahin, O., Yesilel, O. Z. & Frontera, A. (2017a). CrystEngComm, 19, 1389–1399. Web of Science CSD CrossRef CAS Google Scholar
Afkhami, F. A., Khandar, A. A., White, J. M., Guerri, A., Ienco, A., Bryant, J. T., Mhesn, N. & Lampropoulos, C. (2017b). Inorg. Chim. Acta, 457, 150–159. Web of Science CrossRef CAS Google Scholar
Afkhami, F. A., Krautscheid, H., Atioğlu, Z. & Akkurt, M. (2017c). Acta Cryst. E73, 28–30. Web of Science CSD CrossRef IUCr Journals Google Scholar
Akkurt, M., Khandar, A. A., Tahir, M. N., Afkhami, F. A. & Yazdi, S. A. H. (2014). Acta Cryst. E70, m213–m214. CSD CrossRef IUCr Journals Google Scholar
Akkurt, M., Khandar, A. A., Tahir, M. N., Yazdi, S. A. H. & Afkhami, F. A. (2012). Acta Cryst. E68, m842. CSD CrossRef IUCr Journals Google Scholar
Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Khandar, A. A., Afkhami, F. A., Krautscheid, H., Kristoffersen, K. A., Atioğlu, Z., Akkurt, M. & Görbitz, C. H. (2017). Acta Cryst. E73, 698–701. CSD CrossRef IUCr Journals Google Scholar
Khandar, A. A., Ghosh, B. K., Lampropoulos, C., Gargari, M. S., Yilmaz, V. T., Bhar, K., Hosseini-Yazdi, S. A., Cain, J. M. & Mahmoudi, G. (2015). Polyhedron, 85, 467–475. CSD CrossRef CAS Google Scholar
Malekshahian, M., Talei Bavil Olyai, M. R. & Notash, B. (2012). Acta Cryst. E68, m218–m219. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spackman, M. A. & Jayatilaka, D. (2009). CrystEngComm, 11, 19–32. Web of Science CrossRef CAS Google Scholar
Spackman, M. A. & McKinnon, J. J. (2002). CrystEngComm, 4, 378–392. Web of Science CrossRef CAS Google Scholar
Spek, A. L. (2015). Acta Cryst. C71, 9–18. Web of Science CrossRef IUCr Journals Google Scholar
Wolff, S. K., Grimwood, D. J., McKinnon, J. J., Turner, M. J., Jayatilaka, D. & Spackman, M. A. (2012). CrystalExplorer. University of Western Australia. Google Scholar
Yao, S.-Q., Zhu, M.-L., Lu, L.-P. & Gao, X.-L. (2006). Acta Cryst. C62, m183–m185. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
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