research communications
(μ2-Adipato-κ4O,O′:O′′,O′′′)bis[aqua(benzene-1,2-diamine-κ2N,N′)chloridocadmium]: and Hirshfeld surface analysis
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, bDepartment of Chemistry, Kulliyyah of Science, International Islamic University Malaysia, 25200 Kuantan, Pahang, Malaysia, cDepartment of Physics, Bhavan's Sheth R. A. College of Science, Ahmedabad, Gujarat 380 001, India, and dResearch Centre for Crystalline Materials, School of Science and Technology, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia
*Correspondence e-mail: edwardt@sunway.edu.my
The full molecule of the binuclear title compound, [Cd2Cl2(C6H8O4)(C6H8N2)2(H2O)2], is generated by the application of a centre of inversion located at the middle of the central CH2—CH2 bond of the adipate dianion; the latter chelates a CdII atom at each end. Along with two carboxylate-O atoms, the CdII ion is coordinated by the two N atoms of the chelating benzene-1,2-diamine ligand, a Cl− anion and an aqua ligand to define a distorted octahedral CdClN2O3 coordination geometry with the monodentate ligands being mutually cis. The disparity in the Cd—N bond lengths is related to the relative trans effect exerted by the Cd—O bonds formed by the carboxylate-O and aqua-O atoms. The packing features water-O—H⋯O(carboxylate) and benzene-1,2-diamine-N—H⋯Cl hydrogen bonds, leading to layers that stack along the a-axis direction. The lack of directional interactions between the layers is confirmed by a Hirshfeld surface analysis.
Keywords: crystal structure; cadmium; adipic acid; benzene-1,2-diamine; hydrogen bonding.
CCDC reference: 1446968
1. Chemical context
In the +II d10 cadmium(II) cation is a favourite of researchers studying coordination polymers/metal–organic frameworks. With the ability to readily coordinate a variety of different donor atoms, i.e. both hard and soft donors, and to adopt a range of coordination geometries, a diverse array of structures can be generated. The motivation for studying cadmium(II) compounds in this context, over and above intellectual curiosity, rests primarily with evaluating their properties (Lestari et al., 2014; Xue et al., 2015; Seco et al., 2017).
the 4Our interest in cadmium(II) structural chemistry is in the controlled formation (dimensionality and topology) of coordination polymers of dithiophosphates (−S2P(OR)2; Lai & Tiekink, 2004, 2006), (−S2COR; Tan, Azizuddin et al., 2016) and dithiocarbamates (−S2CNR2; Chai et al., 2003), in particular those substituted with hydroxyethyl groups, capable of forming hydrogen-bonding interactions (Tan et al., 2013; Tan, Halim & Tiekink, 2016). In this connection, we now describe the determination and Hirshfeld surface analysis of a cadmium(II) species, (I), with a potentially bridging adipato dianion and an ancillary ligand, benzene-1,2-diamine, capable of forming hydrogen-bonding interactions.
2. Structural commentary
The comprises half a molecule of (I), Fig. 1, with the full molecule generated about a centre of inversion. The key feature of the structure is the tetra-coordinate mode of coordination of the adipato dianion, linking the two CdII cations. Each carboxylate group forms equivalent Cd—O bonds, the difference in the two bonds being only 0.01 Å, Table 1. More asymmetry is found in the coordination of the benzene-1,2-diamine ligand with the Cd—N1 bond length being 0.05 Å longer than Cd—N2. This may be traced to the different trans effects exerted by the oxygen atoms in that the N1 atom is trans to the carboxylate-O1 atom [N1—Cd—O1 = 166.89 (6)°] whereas N2 is opposite to the coordinating water molecule [N2—Cd—O1W = 149.12 (7)°]. The coordination geometry is completed by the chloride anion which, owing to the presence of two chelating ligands, occupies a position cis to the aqua group. The donor set is ClN2O3 and defines a distorted octahedral geometry.
of (I)
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As might be expected, the four-membered chelate ring formed by the carboxylate group is strictly planar (r.m.s. deviation = 0.0009 Å). There is a twist in the chain of the dicarboxylate ligand with the bond linking the quaternary atom to the aliphatic group being + anti-clinal, i.e. the O2—C1—C2—C3 torsion angle is 145.7 (3)° but, - anti-periplanar about the central bond, i.e. C1—C2—C3—C3i is −177.6 (3)°; symmetry code: (i) −x, 2 − y, −z. There is a distinct kink in the five-membered ring formed by the benzene-1,2-diamine ligand. This is readily seen in the dihedral angle of 58.57 (7)° formed between the plane through the CdN2 atoms and the benzene ring.
3. Supramolecular features
As summarized in Table 2, all acidic hydrogen atoms in the molecule of (I) are involved in conventional hydrogen-bonding interactions. The water-H atoms each form an hydrogen bond with a carboxylate-O atom to form strands propagating along the b-axis direction, involving the carboxylate-O1 atoms, and along the c-axis direction, involving the carboxylate-O2 atoms. Thereby, a supramolecular layer is formed parallel to (100), Fig. 2a. Within this framework are benzene-1,2-diamine-N—H⋯Cl hydrogen bonds involving all the amine-H atoms. This has the result that each chloride anion accepts four N—H⋯Cl hydrogen bonds and, to a first approximation exists in a flat, bowl-shaped environment defined by a CdH4 `donor set'. Layers stack along the a axis with no directional interactions between them, Fig. 2b. Given this observation, it was thought worthwhile to perform a Hirshfeld surface analysis to probe the molecular packing in more detail. The results of this analysis are discussed in the next section.
4. Hirshfeld surface analysis
The Hirshfeld surfaces calculated for (I) provide further insight into the supramolecular associations in the crystal; the calculations were performed according to a recent publication (Jotani et al., 2017). The presence of bright-red spots appearing near water-H atoms, H1W and H2W, and carboxylate oxygen atoms, O1 and O2, on the Hirshfeld surface mapped over dnorm in Fig. 3, result from the O—H⋯O hydrogen bonds between these atoms, Table 2. The faint-red spots appearing near each of diamine-hydrogen atoms, H1N–H4N, and those near the Cl1 atom represent the formation of the four comparatively weak N—H⋯Cl interactions. The donors and acceptors of above intermolecular interactions can also be viewed as blue and red regions around the respective atoms on the Hirshfeld surface mapped over the calculated electrostatic potential in Fig. 4. The immediate environment about a reference molecule within the shape-index mapped Hirshfeld surface highlighting intermolecular O—H⋯O, N—H⋯Cl interactions and short interatomic H⋯H contacts is illustrated in Fig. 5.
The overall two-dimensional fingerprint plot, Fig. 6a, and those delineated into H⋯H, O⋯H/H⋯O,Cl⋯H/H⋯Cl and C⋯H/H⋯C contacts (McKinnon et al., 2007) are illustrated in Fig. 6b–e, respectively. The significant contributions from interatomic O⋯H/H⋯O and Cl⋯H/H⋯Cl contacts to the Hirshfeld surfaces, see data in Table 3, result from the involvement of water, diamine, chloride and carboxylate residues in the intermolecular interactions. The relatively high contribution from these atoms decreases the relative importance of interatomic H⋯H contacts, i.e. to 45.4%, to the Hirshfeld surface. The presence of a short interatomic H⋯H contact between water-H1W and methyl-H3A, Table 4, also has an influence upon the molecular packing as shown in Fig. 5. In the fingerprint plot delineated into H⋯H contacts, Fig. 6b, this is viewed as the distribution of points at de + di < sum of their van der Waals radii, i.e. 2.40 Å. Another short inter-atomic H⋯H contact listed in Table 4, involving benzene-H8 atoms lying at the surfaces of the layers stacked along the a axis appear to have little impact upon the packing. The intermolecular O—H⋯O and N—H⋯Cl hydrogen bonding are recognized as the pair of spikes at de + di ∼ 1.8 and 2.5 Å, respectively, together with green points within the distributions in Fig. 6c and d, respectively. The points related to short inter-atomic O⋯H contact between water-O1W and methyl-H3A mentioned above are merged in the plot, Fig. 6c. It can be seen from the fingerprint plot delineated into C⋯H/H⋯C contacts, Fig. 6e, that although these contacts make a significant contribution of 11.2% to the dumbbell-shaped Hirshfeld surface due to the presence of benzene-C atoms, the molecular packing results in inter-atomic C⋯H/H⋯C separations longer than van der Waals contact distances, hence they exert a negligible effect in the crystal. The low contribution from other contacts listed in Table 3 have little effect in the structure due to their large inter-atomic separations.
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5. Database survey
A search of the crystallographic literature (Groom et al., 2016) was undertaken in order to find closely related structures to (I). Reflecting the interest in these structures, there were nearly 50 examples with the adipato dianion. In each case, the dianion bridged two CdII cations via chelating interactions in all but one example. Often, the dicarboxylate ligand also bridged other CdII cations, i.e. was found to be coordinating in μ3- and μ4-modes. The most closely related structure in the literature is illustrated in Scheme 2, i.e. (II) (Che et al., 2013).
The coordination geometry for one of the independent CdII atoms in (II), being defined by two carboxylate-O atoms, derived from a tri-anionic μ2-benzene-1,3,5-tricarboxylato ligand, two nitrogen atoms from a chelating imidazo[4,5-f][1,10]phenanthroline ligand, chlorido and water-O atoms resembles that found in (I); this is illustrated on the left-hand side of Scheme 2. The difference between (I) and (II) is that in (II), the chlorido ligand is bridging, leading to a one-dimensional coordination polymer.
6. Synthesis and crystallization
Benzene-1,2-diamine (0.4324 g, 4 mmol) was slowly added to an aqueous solution (15 ml) of CdCl2·2H2O (0.4026 g, 2 mmol) resulting in a yellow solution. The mixture was stirred for about 1 h when adipic acid (0.2923 g, 2 mmol) in MeOH (10 ml) was added. The mixture then was stirred for a further 3 h. The resultant solution was reduced and left for crystallization. Brown crystals of (I) were obtained after a few weeks and analysed directly.
7. details
Crystal data, data collection and structure . The carbon-bound H-atoms were placed in calculated positions (C—H = 0.95–0.99 Å) and were included in the in the riding model approximation, with Uiso(H) set to 1.2Ueq(C). The O-bound and N-bound H-atoms were located in difference-Fourier maps but were refined with distance restraints of O—H = 0.84±0.01 Å and N—H = 0.88±0.01 Å, and with Uiso(H) set to 1.5Ueq(O) and 1.2Ueq(N). The maximum and minimum residual electron density peaks of 1.15 and 0.69 e Å−3, respectively, were located 0.90 and 0.87 Å from the CdII cation.
details are summarized in Table 5
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Supporting information
CCDC reference: 1446968
https://doi.org/10.1107/S2056989017011677/hb7697sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017011677/hb7697Isup2.hkl
Data collection: CrysAlis PRO (Agilent, 2013); cell
CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); 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) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).[Cd2Cl2(C6H8O4)(C6H8N2)2(H2O)2] | F(000) = 684 |
Mr = 692.14 | Dx = 1.891 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 20.4710 (8) Å | Cell parameters from 7493 reflections |
b = 5.5578 (2) Å | θ = 3.8–30.0° |
c = 10.7910 (3) Å | µ = 2.01 mm−1 |
β = 98.122 (3)° | T = 100 K |
V = 1215.42 (7) Å3 | Prism, brown |
Z = 2 | 0.33 × 0.22 × 0.10 mm |
Agilent Technologies SuperNova Dual diffractometer with Atlas detector | 3393 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 2992 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.039 |
Detector resolution: 10.4041 pixels mm-1 | θmax = 30.3°, θmin = 3.0° |
ω scan | h = −28→26 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | k = −7→7 |
Tmin = 0.842, Tmax = 1.000 | l = −14→14 |
15862 measured reflections |
Refinement on F2 | 6 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.028 | w = 1/[σ2(Fo2) + (0.0312P)2 + 0.8274P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.065 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 1.15 e Å−3 |
3393 reflections | Δρmin = −0.69 e Å−3 |
163 parameters |
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 | ||
Cd | 0.20549 (2) | 0.38825 (3) | 0.25421 (2) | 0.01173 (6) | |
Cl1 | 0.26037 (3) | 0.56615 (11) | 0.45833 (5) | 0.01653 (13) | |
O1 | 0.14096 (9) | 0.7293 (3) | 0.19608 (15) | 0.0172 (4) | |
O2 | 0.13895 (9) | 0.4366 (3) | 0.05909 (15) | 0.0155 (4) | |
O1W | 0.12696 (9) | 0.1564 (3) | 0.31419 (16) | 0.0155 (4) | |
H1W | 0.1293 (15) | 0.026 (3) | 0.277 (3) | 0.023* | |
H2W | 0.1321 (15) | 0.127 (5) | 0.3906 (11) | 0.023* | |
N1 | 0.28158 (11) | 0.0464 (4) | 0.26867 (19) | 0.0149 (4) | |
H1N | 0.2813 (14) | −0.063 (4) | 0.327 (2) | 0.018* | |
H2N | 0.2722 (14) | −0.009 (5) | 0.1919 (14) | 0.018* | |
N2 | 0.29273 (11) | 0.4407 (4) | 0.12990 (19) | 0.0145 (4) | |
H3N | 0.2803 (13) | 0.324 (4) | 0.078 (2) | 0.017* | |
H4N | 0.2981 (14) | 0.582 (3) | 0.097 (3) | 0.017* | |
C1 | 0.12011 (12) | 0.6431 (5) | 0.0893 (2) | 0.0147 (5) | |
C2 | 0.07303 (14) | 0.7824 (6) | −0.0037 (2) | 0.0240 (6) | |
H2A | 0.0485 | 0.6667 | −0.0627 | 0.029* | |
H2B | 0.0991 | 0.8867 | −0.0526 | 0.029* | |
C3 | 0.02372 (12) | 0.9371 (5) | 0.0503 (2) | 0.0165 (5) | |
H3A | 0.0476 | 1.0597 | 0.1059 | 0.020* | |
H3B | −0.0018 | 0.8357 | 0.1017 | 0.020* | |
C4 | 0.34453 (12) | 0.1628 (4) | 0.2844 (2) | 0.0133 (5) | |
C5 | 0.35047 (13) | 0.3687 (4) | 0.2120 (2) | 0.0146 (5) | |
C6 | 0.40716 (12) | 0.5067 (5) | 0.2319 (2) | 0.0169 (5) | |
H6 | 0.4112 | 0.6456 | 0.1822 | 0.020* | |
C7 | 0.45817 (13) | 0.4418 (5) | 0.3248 (2) | 0.0202 (5) | |
H7 | 0.4972 | 0.5360 | 0.3387 | 0.024* | |
C8 | 0.45193 (13) | 0.2395 (5) | 0.3971 (2) | 0.0210 (5) | |
H8 | 0.4866 | 0.1973 | 0.4616 | 0.025* | |
C9 | 0.39589 (13) | 0.0984 (5) | 0.3766 (2) | 0.0177 (5) | |
H9 | 0.3925 | −0.0421 | 0.4254 | 0.021* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cd | 0.01482 (10) | 0.00958 (9) | 0.01025 (9) | 0.00074 (6) | −0.00008 (6) | 0.00069 (6) |
Cl1 | 0.0255 (3) | 0.0120 (3) | 0.0112 (2) | −0.0020 (2) | −0.0006 (2) | −0.0006 (2) |
O1 | 0.0224 (9) | 0.0157 (9) | 0.0127 (8) | 0.0044 (7) | −0.0005 (7) | −0.0009 (7) |
O2 | 0.0200 (9) | 0.0150 (9) | 0.0111 (8) | 0.0031 (7) | 0.0007 (7) | −0.0010 (6) |
O1W | 0.0210 (9) | 0.0138 (9) | 0.0114 (8) | −0.0019 (7) | 0.0015 (7) | 0.0002 (7) |
N1 | 0.0212 (11) | 0.0123 (10) | 0.0109 (9) | −0.0019 (8) | 0.0014 (8) | 0.0008 (8) |
N2 | 0.0214 (11) | 0.0097 (10) | 0.0119 (9) | −0.0005 (8) | 0.0007 (8) | 0.0027 (8) |
C1 | 0.0156 (12) | 0.0162 (12) | 0.0123 (11) | 0.0028 (9) | 0.0027 (9) | 0.0018 (9) |
C2 | 0.0267 (14) | 0.0310 (16) | 0.0133 (11) | 0.0147 (12) | 0.0000 (10) | 0.0009 (11) |
C3 | 0.0189 (13) | 0.0156 (12) | 0.0140 (11) | 0.0057 (10) | −0.0018 (9) | 0.0008 (9) |
C4 | 0.0161 (12) | 0.0124 (11) | 0.0117 (10) | 0.0026 (9) | 0.0025 (9) | −0.0016 (9) |
C5 | 0.0185 (12) | 0.0145 (12) | 0.0112 (11) | 0.0027 (9) | 0.0027 (9) | −0.0012 (9) |
C6 | 0.0206 (13) | 0.0132 (12) | 0.0174 (12) | 0.0010 (10) | 0.0047 (9) | −0.0011 (9) |
C7 | 0.0164 (13) | 0.0221 (14) | 0.0222 (13) | −0.0039 (10) | 0.0038 (10) | −0.0035 (11) |
C8 | 0.0173 (12) | 0.0259 (15) | 0.0188 (12) | 0.0061 (11) | −0.0010 (9) | −0.0014 (10) |
C9 | 0.0221 (13) | 0.0165 (13) | 0.0148 (12) | 0.0042 (10) | 0.0034 (10) | 0.0014 (9) |
Cd—O1 | 2.3448 (17) | C2—C3 | 1.505 (4) |
Cd—O2 | 2.3560 (16) | C2—H2A | 0.9900 |
Cd—N1 | 2.448 (2) | C2—H2B | 0.9900 |
Cd—N2 | 2.398 (2) | C3—C3i | 1.521 (5) |
Cd—Cl1 | 2.5283 (6) | C3—H3A | 0.9900 |
Cd—O1W | 2.2265 (18) | C3—H3B | 0.9900 |
O1—C1 | 1.265 (3) | C4—C9 | 1.389 (3) |
O2—C1 | 1.268 (3) | C4—C5 | 1.400 (3) |
O1W—H1W | 0.834 (10) | C5—C6 | 1.382 (4) |
O1W—H2W | 0.832 (10) | C6—C7 | 1.389 (4) |
N1—C4 | 1.430 (3) | C6—H6 | 0.9500 |
N1—H1N | 0.875 (10) | C7—C8 | 1.385 (4) |
N1—H2N | 0.879 (10) | C7—H7 | 0.9500 |
N2—C5 | 1.431 (3) | C8—C9 | 1.381 (4) |
N2—H3N | 0.871 (10) | C8—H8 | 0.9500 |
N2—H4N | 0.874 (10) | C9—H9 | 0.9500 |
C1—C2 | 1.504 (3) | ||
O1W—Cd—O1 | 98.22 (6) | O2—C1—C2 | 118.9 (2) |
O1W—Cd—O2 | 88.62 (6) | O1—C1—Cd | 59.78 (12) |
O1—Cd—O2 | 55.66 (6) | O2—C1—Cd | 60.29 (12) |
O1W—Cd—N2 | 149.12 (7) | C2—C1—Cd | 179.18 (18) |
O1—Cd—N2 | 100.84 (7) | C1—C2—C3 | 116.0 (2) |
O2—Cd—N2 | 82.44 (7) | C1—C2—H2A | 108.3 |
O1W—Cd—N1 | 90.66 (7) | C3—C2—H2A | 108.3 |
O1—Cd—N1 | 166.89 (6) | C1—C2—H2B | 108.3 |
O2—Cd—N1 | 115.34 (6) | C3—C2—H2B | 108.3 |
N2—Cd—N1 | 67.19 (7) | H2A—C2—H2B | 107.4 |
O1W—Cd—Cl1 | 102.90 (5) | C2—C3—C3i | 112.5 (3) |
O1—Cd—Cl1 | 94.65 (4) | C2—C3—H3A | 109.1 |
O2—Cd—Cl1 | 149.72 (5) | C3i—C3—H3A | 109.1 |
N2—Cd—Cl1 | 99.52 (5) | C2—C3—H3B | 109.1 |
N1—Cd—Cl1 | 92.72 (5) | C3i—C3—H3B | 109.1 |
C1—O1—Cd | 92.43 (14) | H3A—C3—H3B | 107.8 |
C1—O2—Cd | 91.84 (14) | C9—C4—C5 | 119.6 (2) |
Cd—O1W—H1W | 106 (2) | C9—C4—N1 | 123.1 (2) |
Cd—O1W—H2W | 114 (2) | C5—C4—N1 | 116.8 (2) |
H1W—O1W—H2W | 107 (3) | C6—C5—C4 | 120.3 (2) |
C4—N1—Cd | 102.19 (15) | C6—C5—N2 | 122.9 (2) |
C4—N1—H1N | 109.0 (19) | C4—C5—N2 | 116.4 (2) |
Cd—N1—H1N | 121 (2) | C5—C6—C7 | 119.8 (2) |
C4—N1—H2N | 110.0 (19) | C5—C6—H6 | 120.1 |
Cd—N1—H2N | 99 (2) | C7—C6—H6 | 120.1 |
H1N—N1—H2N | 115 (3) | C8—C7—C6 | 119.8 (2) |
C5—N2—Cd | 103.59 (14) | C8—C7—H7 | 120.1 |
C5—N2—H3N | 109 (2) | C6—C7—H7 | 120.1 |
Cd—N2—H3N | 95.4 (19) | C9—C8—C7 | 120.8 (2) |
C5—N2—H4N | 111.2 (19) | C9—C8—H8 | 119.6 |
Cd—N2—H4N | 119 (2) | C7—C8—H8 | 119.6 |
H3N—N2—H4N | 117 (3) | C8—C9—C4 | 119.7 (2) |
O1—C1—O2 | 120.1 (2) | C8—C9—H9 | 120.1 |
O1—C1—C2 | 121.0 (2) | C4—C9—H9 | 120.1 |
Cd—O1—C1—O2 | 0.2 (2) | C9—C4—C5—N2 | −172.4 (2) |
Cd—O1—C1—C2 | −179.7 (2) | N1—C4—C5—N2 | 0.0 (3) |
Cd—O2—C1—O1 | −0.2 (2) | Cd—N2—C5—C6 | −130.3 (2) |
Cd—O2—C1—C2 | 179.7 (2) | Cd—N2—C5—C4 | 42.1 (2) |
O1—C1—C2—C3 | −34.4 (4) | C4—C5—C6—C7 | −0.5 (4) |
O2—C1—C2—C3 | 145.7 (3) | N2—C5—C6—C7 | 171.6 (2) |
C1—C2—C3—C3i | −177.6 (3) | C5—C6—C7—C8 | −0.1 (4) |
Cd—N1—C4—C9 | 131.4 (2) | C6—C7—C8—C9 | 1.1 (4) |
Cd—N1—C4—C5 | −40.8 (2) | C7—C8—C9—C4 | −1.5 (4) |
C9—C4—C5—C6 | 0.2 (4) | C5—C4—C9—C8 | 0.8 (4) |
N1—C4—C5—C6 | 172.6 (2) | N1—C4—C9—C8 | −171.1 (2) |
Symmetry code: (i) −x, −y+2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W···O1ii | 0.83 (2) | 1.90 (2) | 2.728 (2) | 176 (3) |
O1W—H2W···O2iii | 0.83 (1) | 1.84 (1) | 2.670 (2) | 177 (3) |
N1—H1N···Cl1ii | 0.88 (2) | 2.57 (2) | 3.428 (2) | 166 (2) |
N1—H2N···Cl1iv | 0.88 (2) | 2.52 (2) | 3.374 (2) | 165 (2) |
N2—H3N···Cl1iv | 0.87 (2) | 2.53 (2) | 3.385 (2) | 168 (2) |
N2—H4N···Cl1v | 0.88 (2) | 2.52 (2) | 3.322 (2) | 153 (3) |
Symmetry codes: (ii) x, y−1, z; (iii) x, −y−1/2, z−1/2; (iv) x, −y−1/2, z−3/2; (v) x, −y+1/2, z−3/2. |
Contact | Percentage contribution |
H···H | 45.4 |
O···H/H···O | 22.9 |
Cl···H/H···Cl | 19.0 |
C···H/H···C | 11.2 |
C···Cl/Cl···C | 0.7 |
C···C | 0.4 |
Cl···O/O···Cl | 0.3 |
Cd···H/H···Cd | 0.1 |
Contact | Distance | Symmetry operation |
H1W···H3A | 2.32 | x, -1 + y, z |
H8···H8 | 2.38 | 1 - x, - y, 1 - z |
O1W···H3A | 2.64 | x, - 1 + y, z |
Footnotes
‡Additional correspondence author, e-mail: nadiahhalim@um.edu.my
Acknowledgements
We are grateful to the University of Malaya's Postgraduate Research Grant scheme (PPP) for Grant No. PG056–2013B.
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