Two cadmium coordination polymers with bridging acetate and phenyl­enedi­amine ligands that exhibit two-dimensional layered structures

Geiger, D.K.; Parsons, D.E.; Pagano, B.A.

doi:10.1107/S2056989016017382

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ISSN: 2056-9890

Volume 72| Part 12| December 2016| Pages 1718-1723

https://doi.org/10.1107/S2056989016017382

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Two cadmium coordination polymers with bridging acetate and phenylenediamine ligands that exhibit two-dimensional layered structures

David K. Geiger,^a ^* Dylan E. Parsons ^a and Bracco A. Pagano ^a

^aDepartment of Chemistry, SUNY-College at Geneseo, Geneseo, NY 14454, USA
^*Correspondence e-mail: geiger@geneseo.edu

Edited by T. J. Prior, University of Hull, England (Received 20 October 2016; accepted 28 October 2016; online 4 November 2016)

Poly[tetra-μ₂-acetato-κ⁸O:O′-bis(μ₂-benzene-1,2-diamine-κ²N:N′)dicadmium], [Cd₂(CH₃COO)₄(C₆H₈N₂)₂]_n, (I), and poly[[(μ₂-acetato-κ²O:O′)(acetato-κ²O,O′)(μ₂-benzene-1,3-diamine-κ²N:N′)cadmium] hemihydrate], {[Cd(CH₃COO)₂(C₆H₈N₂)]·0.5H₂O}_n, (II), have two-dimensional polymeric structures in which monomeric units are joined by bridging acetate and benzenediamine ligands. Each of the Cd^II ions has an O₄N₂ coordination environment. The coordination geometries of the symmetry-independent Cd^II ions are distorted octahedral and distorted trigonal antiprismatic in (I) and distorted antiprismatic in (II). Both compounds exhibit an intralayer hydrogen-bonding network. In addition, the water of hydration in (II) is involved in interlayer hydrogen bonding.

Keywords: crystal structure; coordination polymer; metal organic framework; cadmium complex.

CCDC references: 1512964; 1512963

1. Chemical context

Cd^II is able to substitute for Zn^II in the active sites of zinc-containing enzymes and to interfere with the metabolism of Ca^II, which are the primary reasons for its toxicity (Borsari, 2014 ). In addition, the substitution of Cd^II for spectroscopically silent Zn^II provides a means of exploring zinc-containing biomolecules using ¹¹¹Cd and ¹¹³Cd NMR spectroscopies (Kimblin & Parkin, 1996 ; Henehan et al., 1993 ; Jalilehvand et al., 2009 , 2012 ). Thus, the coordination chemistry of cadmium is of interest.

Metal–organic frameworks (MOFs) have received much attention because of their many potential applications including gas storage, catalysis, chemical sensors and molecular separation (Dey et al., 2014 ; Kreno et al., 2012 ; Farha & Hupp, 2010 ). Our previous efforts in the area of coordination polymers have focused on compounds based on phenylenediamine and acetate ligands incorporating Zn^II (Geiger & Parsons, 2014 ) and Pb^II (Geiger et al., 2014 ). We have extended this work to include Cd and report the structural analyses of two Cd compounds herein. Although acetate ligands adopt a myriad of different metal-binding modes, only the μ₂-acetato-κ²O:O′ mode is observed in (I). Both acetato-κ²O,O′ and μ₂-acetato-κ²O:O′ modes are found in (II).

Numerous examples of structures with benzene-1,2-diamines exhibiting monodentate and/or bidentate coordination modes have been reported (Narayanan & Bhadbhade, 1996 ; Ovalle-Marroquín et al., 2002 ; Ariyananda & Norman, 2005 ; Chen et al., 2006 ; Maxcy et al., 2000 ; Qian et al., 2007 ; Dickman, 2000 ; Mei et al., 2009 ; Djebli et al., 2012 ; Zick & Geiger, 2016 ; Geiger et al., 2014; Geiger & Parsons, 2014; Geiger, 2012 ). Examples of benzene-1,4-diamine metal-complex structures have also been reported (Batten et al., 2001 ; Faizi & Prisyazhnaya, 2015 ). Few examples of bridging benzene-1,2-diamine-κ²N:N′ (Liang & Qu, 2008 ; Duff, 1968 ), 1,3-diamine-κ²N:N′ (Chemli et al., 2013 ), or benzene-1,4-diamine-κ²N:N′ (Liu et al., 2012 ) ligands have been reported. Compounds (I) and (II) are two new examples of coordination polymers in which benzenediamine ligands bridge two metal atoms.

2. Structural commentary

As shown in Fig. 1, (I) has two symmetry-independent Cd^II ions. Cd1 sits on a crystallographically imposed inversion center and Cd2 resides on a crystallographically imposed twofold rotation axis. Each of the Cd^II ions exhibits an O₄N₂ coordination sphere composed of four bridging κ²O:O′ acetate ligands and two bridging κ²N:N′ benzene-1,2-diamine ligands. For the coordination sphere of Cd1, the twist angles (Muetterties & Guggenberger, 1974 ; Dymock & Palenik, 1975 ) defined employing the triangular face centroids N1O1O3 and N1ⁱⁱⁱO3ⁱⁱⁱO1ⁱⁱⁱ (see Fig. 2) are 52.26 (12), 66.27 (15) and 56.47 (9)°, giving an average value of 60 (5)°. Perfect O_h or D_3d trigonal antiprismatic structures have a twist angle of 60°, whereas a D_3h trigonal prismatic structure has a twist angle of 0°. The coordination sphere of Cd2 exhibits twist angles of 35.49 (8), 45.92 (17) and 45.92 (17)° [average 42 (6)°] using opposite triangular faces O2O4ⁱN2^iv and N2ⁱⁱO4^ivO2^vii (see Fig. 2). The coordination geometry is best described as distorted octahedral with the two nitrogen donor atoms trans for Cd1 and distorted trigonal antiprismatic for Cd2 with O₂N trigonal faces. Selected geometrical parameters are given in Table 1.

Table 1
Selected geometric parameters (Å, °) for (I)

Cd1—O3	2.323 (3)	Cd2—O4ⁱ	2.365 (3)
Cd1—O1	2.332 (3)	Cd2—O2	2.260 (3)
Cd1—N1	2.325 (4)	Cd2—N2ⁱⁱ	2.416 (4)

O3—Cd1—N1	84.79 (12)	O4ⁱ—Cd2—O4^iv	80.73 (15)
O3—Cd1—O1	82.98 (11)	O2ⁱⁱⁱ—Cd2—N2ⁱⁱ	79.40 (12)
N1—Cd1—O1	84.38 (12)	O2—Cd2—N2ⁱⁱ	115.81 (12)
O2ⁱⁱⁱ—Cd2—O2	99.65 (17)	O4ⁱ—Cd2—N2ⁱⁱ	76.91 (12)
O2ⁱⁱⁱ—Cd2—O4ⁱ	156.01 (10)	O4^iv—Cd2—N2ⁱⁱ	85.97 (11)
O2—Cd2—O4ⁱ	93.98 (12)	N2ⁱⁱ—Cd2—N2^v	157.5 (2)
Symmetry codes: (i) -x+1, -y+3, -z+2; (ii) x, y+1, z; (iii) $[-x+1, y, -z+{\script{3\over 2}}]$ ; (iv) $[x, -y+3, z-{\script{1\over 2}}]$ ; (v) $[-x+1, y+1, -z+{\script{3\over 2}}]$ .

Figure 1
The atom-labeling scheme for (I)

. Anisotropic displacement parameters for non-H atoms are drawn at the 30% probability level. [Symmetry codes: (i) −x + 1, −y + 3, −z + 2; (ii) x, y + 1, z; (iii) −x + 1, −y + 2, −z + 2; (iv) x, −y + 3, z − $[{1\over 2}]$ ; (v) x, y − 1, z; (vi) −x + 1, y + 1, −z + $[{3\over 2}]$ ; (vii) −x + 1, y, −z + $[{3\over 2}]$ .]

Figure 2
Representations of the Cd^II coordination environments observed in (I)

and (II)

. Symmetry identifiers are those used in Figs. 1

and 3

The N₂O₄ coordination geometry of (II) can be described as severely distorted trigonal antiprismatic with bidentate acetate oxygen atoms and a κ²N:N′ benzene-1,3-diamine nitrogen atom (O1O2N2ⁱ) forming one of the trigonal faces and two κ²O:O′ acetate ligand oxygen atoms and a nitrogen atom from a κ²N:N′ benzene-1,3-diamine (O3O4ⁱⁱN1) forming the other trigonal face (see Fig. 2). The atom-labeling scheme is shown in Fig. 3. The twist angles are 53.71 (11), 22.56 (8) and 45.38 (13)° [average = 41 (16)°]. As seen in Table 2, the Cd—O bond lengths associated with the bidentate acetate ligand are shorter than those of the bridging, monodentate acetate ligands, as has been observed in other cadmium complexes (Wang et al., 2011 , 2013 ).

Table 2
Selected geometric parameters (Å, °) for (II)

Cd1—O3	2.275 (3)	Cd1—O1	2.374 (4)
Cd1—O4ⁱ	2.301 (3)	Cd1—N2ⁱⁱ	2.388 (4)
Cd1—N1	2.324 (4)	Cd1—O2	2.443 (4)

O3—Cd1—O4ⁱ	79.37 (11)	N1—Cd1—N2ⁱⁱ	101.86 (14)
O3—Cd1—N1	107.45 (13)	O1—Cd1—N2ⁱⁱ	84.00 (13)
O4ⁱ—Cd1—N1	99.25 (13)	O3—Cd1—O2	168.71 (11)
O3—Cd1—O1	114.63 (11)	O4ⁱ—Cd1—O2	98.78 (12)
O4ⁱ—Cd1—O1	85.82 (12)	N1—Cd1—O2	83.83 (13)
N1—Cd1—O1	137.80 (13)	O1—Cd1—O2	54.09 (11)
O3—Cd1—N2ⁱⁱ	86.63 (14)	N2ⁱⁱ—Cd1—O2	91.49 (13)
O4ⁱ—Cd1—N2ⁱⁱ	157.39 (13)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+1, z+{\script{1\over 2}}]$ .

Figure 3
The atom-labeling scheme for (II)

. Anisotropic displacement parameters for non-H atoms are drawn at the 30% probability level. [Symmetry codes: (i) x, −y + 1, z + $[{1\over 2}]$ ; (ii) −x + $[{3\over 2}]$ , y − $[{1\over 2}]$ , −z + $[{3\over 2}]$ ; (iii) −x + $[{3\over 2}]$ , y + $[{1\over 2}]$ , −z + $[{3\over 2}]$ .]

3. Supramolecular features

As seen in Fig. 4, the supramolecular architecture of (I) exhibits independent layers in the bc plane, which are repeated in the [100] direction. Extensive N—H⋯O hydrogen-bonding interactions exist (see Table 3), but none of them extend between the layers. Based on an analysis of the extended structure using the SOLV routine of PLATON (Spek, 2009 ), the unit cell contains no solvent-accessible voids.

Table 3
Hydrogen-bond geometry (Å, °) for (I)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2ⁱⁱⁱ	0.86 (2)	2.34 (2)	3.175 (5)	163 (4)
N1—H1B⋯O4^vi	0.91 (2)	2.21 (3)	3.003 (5)	146 (4)
N1—H1B⋯O4^vii	0.91 (2)	2.38 (4)	3.029 (5)	128 (4)
N2—H2A⋯O3^viii	0.86 (2)	2.30 (2)	3.111 (5)	158 (4)
N2—H2B⋯O3^vi	0.86 (2)	2.64 (2)	3.458 (5)	161 (4)
N2—H2B⋯O4^vi	0.86 (2)	2.55 (4)	2.973 (5)	111 (3)
Symmetry codes: (iii) $[-x+1, y, -z+{\script{3\over 2}}]$ ; (vi) -x+1, -y+2, -z+2; (vii) $[x, -y+2, z-{\script{1\over 2}}]$ ; (viii) x, y-1, z.

Figure 4
Packing diagram for (I)

showing the two-dimensional network parallel to (100). All H atoms have been omitted for clarity.

Compound (II) also exhibits a two-dimensional extended structure. Layers parallel to the bc plane and repeated in the [100] direction are observed as seen in Fig. 5. N—H⋯O(acetate) hydrogen bonds (Table 4) are present within the layers. The water of hydration sits on a crystallographically imposed twofold rotation axis and, as seen in Fig. 6, is involved in O—H⋯O and N—H⋯O hydrogen-bonding interactions (Table 4) that link adjacent layers.

Table 4
Hydrogen-bond geometry (Å, °) for (II)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O2	0.81 (2)	2.06 (4)	2.788 (5)	149 (7)
N1—HN1A⋯O5	0.86 (2)	2.34 (2)	3.183 (4)	166 (4)
N1—HN1B⋯O3ⁱⁱⁱ	0.89 (2)	2.12 (2)	2.991 (5)	166 (5)
N2—HN2A⋯O4^iv	0.87 (2)	2.32 (4)	3.012 (6)	137 (4)
N2—HN2B⋯O1ⁱⁱⁱ	0.88 (2)	2.17 (3)	2.994 (5)	156 (5)
Symmetry codes: (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[x, -y+1, z-{\script{1\over 2}}]$ .

Figure 5
Packing diagram for (II)

showing the layers parallel to (100). H atoms have been omitted for clarity.

Figure 6
Partial packing diagram for (II)

showing the hydrogen-bonded network. Only H atoms involved in the hydrogen-bonded network are shown. [Symmetry codes: (i) −x + 1, y, −z + $[{3\over 2}]$ ; (ii) −x + $[{3\over 2}]$ , y + $[{1\over 2}]$ , −z + $[{3\over 2}]$ ; (iii)x, −y + 1, z − $[{1\over 2}]$ .]

4. Database survey

Examples of cadmium coordination polymers with carboxylate ligands and that exhibit two-dimensional sheet structures have been reported (Li et al., 2014 ; Gao et al., 2004 ; Chen & Zhang, 2014 ; Zhang et al., 2007 ; Liu & Xu, 2005 ; Song et al., 2006 ; Kong et al., 2008a ,b ; Xu et al., 2013 ; Zhuo et al., 2006 ). Cadmium is commonly observed with a trigonal–prismatic or trigonal–antiprismatic coordination geometry, often with one or two capping ligands (Bygott et al., 2007 ; Cherni et al., 2012 ; Uçar et al., 2004 ; Banerjee et al., 2005 ; Keypour et al., 2000 ). Coordination polymers with bridging benzene-1,2-diamine ligands (Liang & Qu, 2008; Duff, 1968), bridging benzene-1,3-diamine ligands (Chemli et al., 2013), and bridging benzene-1,4-diamine ligands (Liu et al., 2012) have been reported

5. Synthesis and crystallization

5.1. Preparation of (I)

213 mg (0.924 mmole) cadmium acetate hydrate were dissolved in 10 mL of ethanol. With stirring, 204 mg (1.89 mmol) of benzene-1,2-diamine were added and the resulting solution was refluxed for 2 h. A white precipitate formed, which was isolated by filtration and dried under vacuum. The yield was quantitative (310 mg). Selected IR bands (diamond anvil, cm⁻¹): 3278 (w), 1532 (s), 1504 (s), 1405 (s). ¹H NMR (400 MHz, dmso-d₆, p.p.m.): 1.87 (s, 6H), 6.35 (m, 2H), 6.35 (m, 2H).

Single crystals were obtained by heating some of the product in N,N′-dimethylformamide and allowing the solution to slowly cool to room temperature. The crystal used for data collection was obtained by cutting a piece from a larger plate.

5.2. Preparation of (II)

230 mg (1.00 mmol) cadmium acetate hydrate were dissolved in 10 mL of ethanol. 217 mg (2.01 mmol) benzene-1,3-diamine were added with stirring. The solution was gently refluxed for 2 h. After chilling the reaction mixture in an ice bath, the precipitate was filtered and dried under vacuum. A yield of 248 mg (71%) was obtained. Selected IR bands (diamond anvil, cm⁻¹): 3425 (b), 3329 (s) 3328 (b), 3137 (m), 1520 (s), 1505 (s), 1400 (s). ¹H NMR (400 MHz, dmso-d₆, p.p.m.): 1.83 (s, 6H), 5.78 (m, 3H), 6.64 (t, 1H). ¹³C NMR (dmso-d₆, p.p.m.): 22.1, 100.5, 103.6, 129.6, 149.5, 178.0.

Clear, brown needles suitable for X-ray analysis were obtained upon slow evaporation of an ethanolic solution of the product. The crystals exhibit a melting range of 441–443 K with decomposition.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 5. For both (I) and (II), all hydrogen atoms were located in difference Fourier maps. The hydrogen atoms were refined using a riding model with a C—H distance of 0.98 Å for the methyl groups and 0.95 Å for the phenyl carbon atoms. The methyl hydrogen atom isotropic displacement parameters were set using the approximation U_iso(H) = 1.5U_eq(C). All other C—H hydrogen atom isotropic displacement parameters were set using the approximation U_iso(H) = 1.2U_eq(C). The N—H bond lengths were restrained to 0.88 Å in (I) and (II). The O—H bond length of the water of hydration in (II) was restrained to 0.84 Å and the H—O—H angle was restrained to 105°. U_iso(H) was refined freely for the amine and water hydrogen atoms, except that for (II) the isotropic displacement parameters of the hydrogen atoms associated with N2 were restrained to be the same.

Table 5
Experimental details

	(I)	(II)
Crystal data
Chemical formula	[Cd₂(C₂H₃O₂)₄(C₆H₈N₂)₂]	[Cd(C₂H₃O₂)₂(C₆H₈N₂)]·0.5H₂O
M_r	338.63	695.28
Crystal system, space group	Monoclinic, C2/c	Monoclinic, C2/c
Temperature (K)	200	200
a, b, c (Å)	23.283 (3), 7.2399 (9), 14.2744 (16)	20.777 (6), 8.2374 (18), 15.002 (4)
β (°)	96.887 (4)	102.583 (9)
V (Å³)	2388.8 (5)	2505.9 (11)
Z	8	4
Radiation type	Mo Kα	Mo Kα
μ (mm⁻¹)	1.83	1.75
Crystal size (mm)	0.40 × 0.40 × 0.05	0.40 × 0.08 × 0.08

Data collection
Diffractometer	Bruker SMART X2S benchtop	Bruker SMART X2S benchtop
Absorption correction	Multi-scan (SADABS; Bruker, 2013 )	Multi-scan (SADABS; Bruker, 2013)
T_min, T_max	0.53, 0.91	0.69, 0.87
No. of measured, independent and observed [I > 2σ(I)] reflections	14588, 2263, 1633	8942, 2443, 1859
R_int	0.089	0.057
(sin θ/λ)_max (Å⁻¹)	0.610	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.109, 1.05	0.037, 0.095, 0.99
No. of reflections	2263	2443
No. of parameters	174	180
No. of restraints	4	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.14, −1.17	0.86, −1.02
Computer programs: APEX2 and SAINT (Bruker, 2013), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), PLATON (Spek, 2009), Mercury (Macrae et al., 2006 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC references: 1512964; 1512963

Crystal structure: contains datablocks global, I, II. DOI: https://doi.org/10.1107/S2056989016017382/pj2037sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989016017382/pj2037Isup2.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989016017382/pj2037IIsup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989016017382/pj2037Isup4.mol

Supporting information file. DOI: https://doi.org/10.1107/S2056989016017382/pj2037IIsup5.mol

checkCIF report

Computing details top

For both compounds, data collection: APEX2 (Bruker, 2013); cell refinement: APEX2 (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

(I) Poly[tetra-µ₂-acetato-κ⁸O:O'-bis(µ₂-benzene-1,2-diamine-κ²N:N')dicadmium] top

Crystal data top

[Cd₂(C₂H₃O₂)₄(C₆H₈N₂)₂]	F(000) = 1344
M_r = 338.63	D_x = 1.883 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 23.283 (3) Å	Cell parameters from 120 reflections
b = 7.2399 (9) Å	θ = 3.5–24.0°
c = 14.2744 (16) Å	µ = 1.83 mm⁻¹
β = 96.887 (4)°	T = 200 K
V = 2388.8 (5) Å³	Plate, clear colourless
Z = 8	0.40 × 0.40 × 0.05 mm

Data collection top

Bruker SMART X2S benchtop diffractometer	2263 independent reflections
Radiation source: sealed microfocus tube	1633 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	R_int = 0.089
Detector resolution: 8.3330 pixels mm^-1	θ_max = 25.7°, θ_min = 2.9°
ω scans	h = −28→27
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −8→8
T_min = 0.53, T_max = 0.91	l = −17→16
14588 measured reflections

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) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0496P)² + 0.5909P] where P = (F_o² + 2F_c²)/3
2263 reflections	(Δ/σ)_max < 0.001
174 parameters	Δρ_max = 1.14 e Å⁻³
4 restraints	Δρ_min = −1.17 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	U_iso*/U_eq
Cd1	0.5	1.0	1.0	0.02022 (18)
Cd2	0.5	1.48311 (6)	0.75	0.02246 (18)
O1	0.53894 (13)	1.2329 (4)	0.91404 (19)	0.0280 (7)
O2	0.57421 (14)	1.2817 (4)	0.7785 (2)	0.0341 (8)
O3	0.43034 (13)	1.2226 (4)	1.01819 (19)	0.0287 (8)
O4	0.44787 (12)	1.2680 (4)	1.17354 (18)	0.0275 (7)
N1	0.44368 (16)	0.9351 (5)	0.8581 (2)	0.0220 (8)
H1A	0.4354 (19)	1.040 (4)	0.831 (3)	0.033 (14)*
H1B	0.4683 (16)	0.875 (6)	0.824 (3)	0.045 (15)*
N2	0.44711 (17)	0.5481 (6)	0.8818 (2)	0.0226 (8)
H2A	0.438 (2)	0.445 (4)	0.905 (3)	0.040 (15)*
H2B	0.4719 (16)	0.612 (6)	0.917 (3)	0.044 (15)*
C1	0.39101 (18)	0.8316 (6)	0.8544 (3)	0.0232 (10)
C2	0.39284 (18)	0.6415 (6)	0.8678 (3)	0.0213 (10)
C3	0.3425 (2)	0.5424 (7)	0.8632 (3)	0.0315 (12)
H3	0.344	0.4118	0.8697	0.038*
C4	0.2890 (2)	0.6318 (8)	0.8489 (3)	0.0409 (13)
H4	0.2541	0.5629	0.8467	0.049*
C5	0.2872 (2)	0.8209 (8)	0.8380 (3)	0.0403 (13)
H5	0.251	0.8824	0.829	0.048*
C6	0.3376 (2)	0.9219 (7)	0.8400 (3)	0.0326 (11)
H6	0.336	1.052	0.8316	0.039*
C7	0.57788 (19)	1.2169 (6)	0.8615 (3)	0.0267 (11)
C8	0.6357 (3)	1.1326 (10)	0.8978 (4)	0.0650 (18)
H8A	0.6648	1.2304	0.9089	0.098*
H8B	0.6473	1.0454	0.8511	0.098*
H8C	0.6324	1.0673	0.9571	0.098*
C9	0.41522 (19)	1.2753 (6)	1.0965 (3)	0.0248 (10)
C10	0.3540 (2)	1.3437 (8)	1.0964 (3)	0.0450 (14)
H10A	0.3441	1.3462	1.1612	0.067*
H10B	0.3274	1.2609	1.0581	0.067*
H10C	0.3507	1.4686	1.0697	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.0250 (3)	0.0215 (3)	0.0140 (3)	−0.00045 (16)	0.0019 (2)	−0.00028 (16)
Cd2	0.0275 (3)	0.0228 (3)	0.0180 (3)	0	0.0066 (2)	0
O1	0.0330 (18)	0.0259 (18)	0.0270 (16)	0.0015 (14)	0.0107 (14)	0.0053 (14)
O2	0.047 (2)	0.034 (2)	0.0226 (18)	0.0065 (16)	0.0110 (14)	0.0081 (15)
O3	0.0396 (18)	0.0311 (19)	0.0166 (16)	0.0122 (15)	0.0083 (13)	0.0014 (14)
O4	0.0324 (18)	0.0324 (19)	0.0173 (16)	−0.0035 (15)	0.0010 (14)	−0.0029 (14)
N1	0.030 (2)	0.018 (2)	0.017 (2)	0.0000 (18)	0.0014 (16)	0.0001 (17)
N2	0.032 (2)	0.021 (2)	0.016 (2)	−0.0048 (19)	0.0047 (17)	0.0002 (18)
C1	0.032 (3)	0.028 (3)	0.010 (2)	−0.001 (2)	0.0050 (18)	−0.0021 (18)
C2	0.028 (2)	0.023 (2)	0.012 (2)	0.0015 (19)	0.0038 (18)	−0.0012 (18)
C3	0.039 (3)	0.030 (3)	0.026 (3)	−0.008 (2)	0.007 (2)	−0.004 (2)
C4	0.033 (3)	0.051 (4)	0.038 (3)	−0.006 (3)	0.004 (2)	−0.001 (3)
C5	0.030 (3)	0.049 (4)	0.041 (3)	0.011 (3)	0.004 (2)	0.003 (3)
C6	0.032 (3)	0.035 (3)	0.029 (3)	0.006 (2)	0.000 (2)	−0.002 (2)
C7	0.029 (3)	0.023 (3)	0.028 (3)	0.003 (2)	0.004 (2)	0.001 (2)
C8	0.065 (4)	0.066 (5)	0.065 (4)	0.004 (4)	0.013 (3)	0.002 (4)
C9	0.030 (2)	0.017 (2)	0.028 (3)	−0.0014 (19)	0.009 (2)	0.000 (2)
C10	0.036 (3)	0.063 (4)	0.036 (3)	0.016 (3)	0.006 (2)	−0.004 (3)

Geometric parameters (Å, º) top

C1—C6	1.398 (6)	Cd1—O1ⁱ	2.332 (3)
C1—C2	1.390 (6)	Cd1—N1	2.325 (4)
C10—H10C	0.98	Cd1—N1ⁱ	2.325 (4)
C10—H10B	0.98	Cd2—O4ⁱⁱ	2.365 (3)
C10—H10A	0.98	Cd2—O4ⁱⁱⁱ	2.365 (3)
C2—C3	1.369 (6)	Cd2—O2^iv	2.260 (3)
C3—H3	0.95	Cd2—O2	2.260 (3)
C3—C4	1.398 (7)	Cd2—N2^v	2.416 (4)
C4—H4	0.95	Cd2—N2^vi	2.416 (4)
C4—C5	1.378 (7)	N1—H1B	0.907 (19)
C5—H5	0.95	N1—H1A	0.864 (19)
C5—C6	1.378 (7)	N1—C1	1.432 (5)
C6—H6	0.95	N2—H2B	0.857 (19)
C7—C8	1.512 (7)	N2—H2A	0.86 (2)
C8—H8C	0.98	N2—Cd2^vii	2.415 (4)
C8—H8B	0.98	N2—C2	1.426 (6)
C8—H8A	0.98	O1—C7	1.250 (5)
C9—C10	1.509 (6)	O2—C7	1.267 (5)
Cd1—O3ⁱ	2.323 (3)	O3—C9	1.270 (5)
Cd1—O3	2.323 (3)	O4—Cd2ⁱⁱ	2.365 (3)
Cd1—O1	2.332 (3)	O4—C9	1.261 (5)

O3ⁱ—Cd1—O3	180.00 (13)	C2—N2—H2A	102 (3)
O3ⁱ—Cd1—N1	95.21 (12)	Cd2^vii—N2—H2A	108 (3)
O3—Cd1—N1	84.79 (12)	C2—N2—H2B	110 (4)
O3ⁱ—Cd1—N1ⁱ	84.79 (12)	Cd2^vii—N2—H2B	101 (3)
O3—Cd1—N1ⁱ	95.21 (12)	H2A—N2—H2B	115 (4)
N1—Cd1—N1ⁱ	180.0	C2—C1—C6	119.7 (4)
O3ⁱ—Cd1—O1	97.02 (11)	C2—C1—N1	120.1 (4)
O3—Cd1—O1	82.98 (11)	C6—C1—N1	120.2 (4)
N1—Cd1—O1	84.38 (12)	C3—C2—C1	120.1 (4)
N1ⁱ—Cd1—O1	95.62 (12)	C3—C2—N2	119.8 (4)
O3ⁱ—Cd1—O1ⁱ	82.98 (11)	C1—C2—N2	120.1 (4)
O3—Cd1—O1ⁱ	97.02 (11)	C2—C3—C4	120.5 (5)
N1—Cd1—O1ⁱ	95.62 (12)	C2—C3—H3	119.8
N1ⁱ—Cd1—O1ⁱ	84.38 (12)	C4—C3—H3	119.8
O1—Cd1—O1ⁱ	180.0	C5—C4—C3	119.4 (5)
O2^iv—Cd2—O2	99.65 (17)	C5—C4—H4	120.3
O2^iv—Cd2—O4ⁱⁱ	156.01 (10)	C3—C4—H4	120.3
O2—Cd2—O4ⁱⁱ	93.98 (12)	C4—C5—C6	120.7 (5)
O2^iv—Cd2—O4ⁱⁱⁱ	93.98 (11)	C4—C5—H5	119.6
O2—Cd2—O4ⁱⁱⁱ	156.01 (10)	C6—C5—H5	119.6
O4ⁱⁱ—Cd2—O4ⁱⁱⁱ	80.73 (15)	C5—C6—C1	119.6 (5)
O2^iv—Cd2—N2^v	79.40 (12)	C5—C6—H6	120.2
O2—Cd2—N2^v	115.81 (12)	C1—C6—H6	120.2
O4ⁱⁱ—Cd2—N2^v	76.91 (12)	O1—C7—O2	123.6 (4)
O4ⁱⁱⁱ—Cd2—N2^v	85.97 (11)	O1—C7—C8	120.8 (4)
O2^iv—Cd2—N2^vi	115.81 (12)	O2—C7—C8	115.3 (4)
O2—Cd2—N2^vi	79.40 (12)	C7—C8—H8A	109.5
O4ⁱⁱ—Cd2—N2^vi	85.97 (12)	C7—C8—H8B	109.5
O4ⁱⁱⁱ—Cd2—N2^vi	76.91 (12)	H8A—C8—H8B	109.5
N2^v—Cd2—N2^vi	157.5 (2)	C7—C8—H8C	109.5
C7—O1—Cd1	127.2 (3)	H8A—C8—H8C	109.5
C7—O2—Cd2	111.8 (3)	H8B—C8—H8C	109.5
C9—O3—Cd1	125.3 (3)	O4—C9—O3	123.6 (4)
C9—O4—Cd2ⁱⁱ	126.4 (3)	O4—C9—C10	119.1 (4)
C1—N1—Cd1	121.9 (2)	O3—C9—C10	117.3 (4)
C1—N1—H1A	107 (3)	C9—C10—H10A	109.5
Cd1—N1—H1A	107 (3)	C9—C10—H10B	109.5
C1—N1—H1B	109 (3)	H10A—C10—H10B	109.5
Cd1—N1—H1B	104 (3)	C9—C10—H10C	109.5
H1A—N1—H1B	107 (4)	H10A—C10—H10C	109.5
C2—N2—Cd2^vii	120.6 (2)	H10B—C10—H10C	109.5

Cd1—N1—C1—C2	−75.0 (4)	C4—C5—C6—C1	−0.8 (7)
Cd1—N1—C1—C6	103.1 (4)	C2—C1—C6—C5	−0.9 (6)
C6—C1—C2—C3	2.6 (6)	N1—C1—C6—C5	−179.0 (4)
N1—C1—C2—C3	−179.3 (4)	Cd1—O1—C7—O2	131.3 (4)
C6—C1—C2—N2	179.5 (4)	Cd1—O1—C7—C8	−54.7 (6)
N1—C1—C2—N2	−2.4 (6)	Cd2—O2—C7—O1	13.3 (6)
Cd2^vii—N2—C2—C3	99.3 (4)	Cd2—O2—C7—C8	−160.9 (4)
Cd2^vii—N2—C2—C1	−77.6 (5)	Cd2ⁱⁱ—O4—C9—O3	100.8 (5)
C1—C2—C3—C4	−2.7 (6)	Cd2ⁱⁱ—O4—C9—C10	−81.4 (5)
N2—C2—C3—C4	−179.6 (4)	Cd1—O3—C9—O4	26.7 (6)
C2—C3—C4—C5	1.0 (7)	Cd1—O3—C9—C10	−151.1 (4)
C3—C4—C5—C6	0.8 (7)

Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) −x+1, −y+3, −z+2; (iii) x, −y+3, z−1/2; (iv) −x+1, y, −z+3/2; (v) x, y+1, z; (vi) −x+1, y+1, −z+3/2; (vii) x, y−1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2^iv	0.86 (2)	2.34 (2)	3.175 (5)	163 (4)
N1—H1B···O4ⁱ	0.91 (2)	2.21 (3)	3.003 (5)	146 (4)
N1—H1B···O4^viii	0.91 (2)	2.38 (4)	3.029 (5)	128 (4)
N2—H2A···O3^vii	0.86 (2)	2.30 (2)	3.111 (5)	158 (4)
N2—H2B···O3ⁱ	0.86 (2)	2.64 (2)	3.458 (5)	161 (4)
N2—H2B···O4ⁱ	0.86 (2)	2.55 (4)	2.973 (5)	111 (3)
C8—H8C···O3ⁱ	0.98	2.61	3.295 (7)	127

Symmetry codes: (i) −x+1, −y+2, −z+2; (iv) −x+1, y, −z+3/2; (vii) x, y−1, z; (viii) x, −y+2, z−1/2.

(II) Poly[[(µ₂-acetato-κ²O:O')(acetato-κ²O,O')(µ₂-benzene-1,3-diamine-κ²N:N')cadmium] hemihydrate] top

Crystal data top

[Cd(C₂H₃O₂)₂(C₆H₈N₂)]·0.5H₂O	F(000) = 1384
M_r = 695.28	D_x = 1.843 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 20.777 (6) Å	Cell parameters from 2588 reflections
b = 8.2374 (18) Å	θ = 2.7–23.5°
c = 15.002 (4) Å	µ = 1.75 mm⁻¹
β = 102.583 (9)°	T = 200 K
V = 2505.9 (11) Å³	Needle, clear brown
Z = 4	0.40 × 0.08 × 0.08 mm

Data collection top

Bruker SMART X2S benchtop diffractometer	2443 independent reflections
Radiation source: sealed microfocus tube	1859 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	R_int = 0.057
Detector resolution: 8.3330 pixels mm^-1	θ_max = 26.0°, θ_min = 2.7°
ω scans	h = −25→25
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −9→10
T_min = 0.69, T_max = 0.87	l = −18→11
8942 measured reflections

Refinement top

Refinement on F²	6 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.095	w = 1/[σ²(F_o²) + (0.0489P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max = 0.001
2443 reflections	Δρ_max = 0.86 e Å⁻³
180 parameters	Δρ_min = −1.02 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cd1	0.69991 (2)	0.34064 (4)	0.80989 (2)	0.02831 (14)
O1	0.68026 (16)	0.1764 (4)	0.9313 (2)	0.0381 (9)
O2	0.59435 (17)	0.3087 (4)	0.8546 (2)	0.0436 (9)
O3	0.80578 (15)	0.3370 (3)	0.7917 (3)	0.0357 (8)
O4	0.79978 (15)	0.6013 (4)	0.7691 (2)	0.0375 (8)
O5	0.5	0.5121 (7)	0.75	0.0581 (16)
H5	0.517 (3)	0.455 (4)	0.792 (2)	0.09 (2)*
N1	0.63907 (19)	0.5002 (5)	0.6938 (3)	0.0281 (9)
HN1A	0.6021 (14)	0.522 (5)	0.708 (3)	0.039 (15)*
HN1B	0.649 (2)	0.605 (3)	0.701 (3)	0.039 (14)*
N2	0.7361 (2)	0.4639 (5)	0.4277 (3)	0.0328 (9)
HN2A	0.750 (2)	0.394 (5)	0.393 (3)	0.044 (11)*
HN2B	0.7682 (17)	0.526 (5)	0.457 (3)	0.044 (11)*
C1	0.6204 (2)	0.2190 (6)	0.9196 (3)	0.0316 (11)
C2	0.5810 (3)	0.1613 (6)	0.9855 (4)	0.0553 (16)
H2A	0.5764	0.2496	1.0275	0.083*
H2B	0.6034	0.0692	1.0204	0.083*
H2C	0.5372	0.1272	0.952	0.083*
C3	0.8315 (2)	0.4712 (5)	0.7778 (3)	0.0283 (10)
C4	0.9037 (2)	0.4701 (6)	0.7760 (4)	0.0423 (13)
H4A	0.9093	0.5044	0.7156	0.064*
H4B	0.9213	0.3602	0.7888	0.064*
H4C	0.9275	0.5451	0.8224	0.064*
C5	0.6364 (2)	0.4410 (5)	0.6031 (3)	0.0276 (10)
C6	0.6875 (2)	0.4739 (5)	0.5613 (3)	0.0292 (11)
H6	0.7238	0.5375	0.5921	0.035*
C7	0.6866 (2)	0.4152 (5)	0.4748 (3)	0.0314 (11)
C8	0.6335 (3)	0.3195 (6)	0.4305 (4)	0.0463 (14)
H8	0.6327	0.2769	0.3714	0.056*
C9	0.5833 (3)	0.2881 (7)	0.4720 (4)	0.0573 (17)
H9	0.5473	0.2237	0.4413	0.069*
C10	0.5832 (3)	0.3481 (5)	0.5588 (4)	0.0436 (14)
H10	0.5475	0.3258	0.5871	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.0331 (2)	0.0280 (2)	0.0254 (2)	0.00293 (14)	0.00988 (14)	−0.00140 (14)
O1	0.0347 (19)	0.045 (2)	0.036 (2)	0.0083 (15)	0.0105 (16)	0.0041 (15)
O2	0.043 (2)	0.049 (2)	0.038 (2)	0.0063 (16)	0.0066 (17)	0.0087 (16)
O3	0.0333 (17)	0.0217 (17)	0.056 (2)	−0.0019 (13)	0.0175 (17)	0.0015 (15)
O4	0.0414 (19)	0.0292 (17)	0.047 (2)	0.0059 (15)	0.0204 (17)	0.0114 (15)
O5	0.044 (3)	0.065 (4)	0.058 (4)	0	−0.004 (3)	0
N1	0.032 (2)	0.029 (2)	0.026 (2)	−0.0001 (19)	0.0113 (17)	0.0008 (17)
N2	0.041 (2)	0.036 (2)	0.024 (2)	−0.0003 (19)	0.0143 (18)	−0.0007 (18)
C1	0.033 (3)	0.035 (3)	0.028 (3)	−0.006 (2)	0.011 (2)	−0.005 (2)
C2	0.041 (3)	0.073 (4)	0.054 (4)	0.004 (3)	0.014 (3)	0.014 (3)
C3	0.033 (2)	0.033 (3)	0.021 (2)	−0.001 (2)	0.0095 (19)	−0.0018 (18)
C4	0.036 (3)	0.045 (3)	0.045 (3)	−0.006 (2)	0.007 (2)	0.004 (2)
C5	0.034 (2)	0.025 (2)	0.022 (2)	0.0006 (19)	0.002 (2)	0.0044 (17)
C6	0.029 (2)	0.030 (2)	0.027 (2)	−0.0059 (19)	0.002 (2)	0.0020 (19)
C7	0.041 (3)	0.025 (2)	0.029 (3)	0.004 (2)	0.011 (2)	0.0054 (19)
C8	0.070 (4)	0.043 (3)	0.027 (3)	−0.020 (3)	0.013 (3)	−0.008 (2)
C9	0.070 (4)	0.064 (4)	0.037 (3)	−0.041 (3)	0.009 (3)	−0.014 (3)
C10	0.044 (3)	0.052 (3)	0.035 (3)	−0.025 (2)	0.012 (2)	−0.001 (2)

Geometric parameters (Å, º) top

Cd1—O3	2.275 (3)	C1—C2	1.492 (8)
Cd1—O4ⁱ	2.301 (3)	C2—H2A	0.98
Cd1—N1	2.324 (4)	C2—H2B	0.98
Cd1—O1	2.374 (4)	C2—H2C	0.98
Cd1—N2ⁱⁱ	2.388 (4)	C3—C4	1.506 (6)
Cd1—O2	2.443 (4)	C4—H4A	0.98
O1—C1	1.268 (5)	C4—H4B	0.98
O2—C1	1.249 (5)	C4—H4C	0.98
O3—C3	1.265 (5)	C5—C6	1.374 (6)
O4—C3	1.250 (5)	C5—C10	1.388 (6)
O4—Cd1ⁱⁱⁱ	2.301 (3)	C6—C7	1.381 (6)
O5—H5	0.808 (18)	C6—H6	0.95
N1—C5	1.435 (6)	C7—C8	1.401 (6)
N1—HN1A	0.859 (19)	C8—C9	1.350 (8)
N1—HN1B	0.886 (19)	C8—H8	0.95
N2—C7	1.425 (6)	C9—C10	1.394 (8)
N2—Cd1^iv	2.388 (4)	C9—H9	0.95
N2—HN2A	0.870 (19)	C10—H10	0.95
N2—HN2B	0.877 (19)

O3—Cd1—O4ⁱ	79.37 (11)	C1—C2—H2A	109.5
O3—Cd1—N1	107.45 (13)	C1—C2—H2B	109.5
O4ⁱ—Cd1—N1	99.25 (13)	H2A—C2—H2B	109.5
O3—Cd1—O1	114.63 (11)	C1—C2—H2C	109.5
O4ⁱ—Cd1—O1	85.82 (12)	H2A—C2—H2C	109.5
N1—Cd1—O1	137.80 (13)	H2B—C2—H2C	109.5
O3—Cd1—N2ⁱⁱ	86.63 (14)	O4—C3—O3	122.3 (4)
O4ⁱ—Cd1—N2ⁱⁱ	157.39 (13)	O4—C3—C4	120.5 (4)
N1—Cd1—N2ⁱⁱ	101.86 (14)	O3—C3—C4	117.1 (4)
O1—Cd1—N2ⁱⁱ	84.00 (13)	C3—C4—H4A	109.5
O3—Cd1—O2	168.71 (11)	C3—C4—H4B	109.5
O4ⁱ—Cd1—O2	98.78 (12)	H4A—C4—H4B	109.5
N1—Cd1—O2	83.83 (13)	C3—C4—H4C	109.5
O1—Cd1—O2	54.09 (11)	H4A—C4—H4C	109.5
N2ⁱⁱ—Cd1—O2	91.49 (13)	H4B—C4—H4C	109.5
C1—O1—Cd1	93.7 (3)	C6—C5—C10	120.3 (5)
C1—O2—Cd1	91.0 (3)	C6—C5—N1	119.4 (4)
C3—O3—Cd1	117.6 (3)	C10—C5—N1	120.3 (5)
C3—O4—Cd1ⁱⁱⁱ	136.7 (3)	C5—C6—C7	120.4 (4)
C5—N1—Cd1	114.9 (3)	C5—C6—H6	119.8
C5—N1—HN1A	117 (3)	C7—C6—H6	119.8
Cd1—N1—HN1A	108 (3)	C6—C7—C8	119.4 (5)
C5—N1—HN1B	114 (3)	C6—C7—N2	120.2 (4)
Cd1—N1—HN1B	113 (3)	C8—C7—N2	120.1 (5)
HN1A—N1—HN1B	88 (4)	C9—C8—C7	119.8 (5)
C7—N2—Cd1^iv	114.3 (3)	C9—C8—H8	120.1
C7—N2—HN2A	119 (3)	C7—C8—H8	120.1
Cd1^iv—N2—HN2A	96 (3)	C8—C9—C10	121.4 (5)
C7—N2—HN2B	118 (4)	C8—C9—H9	119.3
Cd1^iv—N2—HN2B	94 (3)	C10—C9—H9	119.3
HN2A—N2—HN2B	111 (5)	C5—C10—C9	118.7 (5)
O2—C1—O1	121.0 (5)	C5—C10—H10	120.6
O2—C1—C2	120.0 (4)	C9—C10—H10	120.6
O1—C1—C2	119.0 (4)

Cd1—O2—C1—O1	−4.6 (4)	N1—C5—C6—C7	178.6 (4)
Cd1—O2—C1—C2	174.9 (4)	C5—C6—C7—C8	−1.0 (7)
Cd1—O1—C1—O2	4.8 (5)	C5—C6—C7—N2	173.2 (4)
Cd1—O1—C1—C2	−174.8 (4)	Cd1^iv—N2—C7—C6	−103.9 (4)
Cd1ⁱⁱⁱ—O4—C3—O3	−148.4 (4)	Cd1^iv—N2—C7—C8	70.2 (5)
Cd1ⁱⁱⁱ—O4—C3—C4	34.3 (6)	C6—C7—C8—C9	1.1 (8)
Cd1—O3—C3—O4	−3.8 (6)	N2—C7—C8—C9	−173.1 (5)
Cd1—O3—C3—C4	173.5 (3)	C7—C8—C9—C10	−0.4 (9)
Cd1—N1—C5—C6	−82.6 (4)	C6—C5—C10—C9	0.6 (7)
Cd1—N1—C5—C10	95.9 (4)	N1—C5—C10—C9	−177.9 (5)
C10—C5—C6—C7	0.1 (6)	C8—C9—C10—C5	−0.5 (9)

Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) x, −y+1, z+1/2; (iii) −x+3/2, y+1/2, −z+3/2; (iv) x, −y+1, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O2	0.81 (2)	2.06 (4)	2.788 (5)	149 (7)
N1—HN1A···O5	0.86 (2)	2.34 (2)	3.183 (4)	166 (4)
N1—HN1B···O3ⁱⁱⁱ	0.89 (2)	2.12 (2)	2.991 (5)	166 (5)
N2—HN2A···O4^iv	0.87 (2)	2.32 (4)	3.012 (6)	137 (4)
N2—HN2B···O1ⁱⁱⁱ	0.88 (2)	2.17 (3)	2.994 (5)	156 (5)
C6—H6···O1ⁱⁱⁱ	0.95	2.39	3.195 (5)	142

Symmetry codes: (iii) −x+3/2, y+1/2, −z+3/2; (iv) x, −y+1, z−1/2.

Acknowledgements

This work was supported by a Congressionally directed grant from the US Department of Education (grant No. P116Z100020) for the X-ray diffractometer and a grant from the Geneseo Foundation.

References

Ariyananda, W. G. P. & Norman, R. E. (2005). Acta Cryst. E61, m187–m189. Web of Science CSD CrossRef IUCr Journals Google Scholar
Banerjee, S., Ghosh, A., Wu, B., Lassahn, P.-G. & Janiak, C. (2005). Polyhedron, 24, 593–599. Web of Science CSD CrossRef CAS Google Scholar
Batten, S. R., McKenzie, C. J. & Nielsen, L. P. (2001). Acta Cryst. C57, 156–157. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Borsari, M. (2014). Cadmium: Coordination Chemistry in Encyclopedia of Inorganic and Bioinorganic Chemistry, pp. 1–16 New York: Wiley. Google Scholar
Bruker (2013). APEX2, SAINT, SADABS, and XSHELL. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bygott, A. M. T., Geue, R. J., Ralph, S. F., Sargeson, A. M. & Willis, A. C. (2007). Dalton Trans. pp. 4778–4748. Web of Science CSD CrossRef Google Scholar
Chemli, R., Kamoun, S. & Roisnel, T. (2013). Acta Cryst. E69, m670–m671. CSD CrossRef IUCr Journals Google Scholar
Chen, H.-R. & Zhang, W.-W. (2014). Acta Cryst. C70, 1079–1082. Web of Science CSD CrossRef IUCr Journals Google Scholar
Chen, Z.-L., Zhang, Y.-Z. & Liang, F.-P. (2006). Acta Cryst. E62, m1296–m1297. Web of Science CSD CrossRef IUCr Journals Google Scholar
Cherni, S. N., Cherni, A. & Driss, A. (2012). X-ray Struct. Anal. Online, 28, 13–14. CSD CrossRef CAS Google Scholar
Dey, C., Kundu, T., Biswal, B. P., Mallick, A. & Banerjee, R. (2014). Acta Cryst. B70, 3–10. Web of Science CrossRef CAS IUCr Journals Google Scholar
Dickman, M. H. (2000). Acta Cryst. C56, 58–60. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Djebli, Y., Boufas, S., Bencharif, L., Roisnel, T. & Bencharif, M. (2012). Acta Cryst. E68, m1411–m1412. CSD CrossRef IUCr Journals Google Scholar
Duff, E. J. (1968). J. Chem. Soc. A, pp. 434–437. CrossRef Web of Science Google Scholar
Dymock, K. R. & Palenik, G. J. (1975). Inorg. Chem. 14, 1220–1222. CrossRef CAS Web of Science Google Scholar
Faizi, M. S. H. & Prisyazhnaya, E. V. (2015). Acta Cryst. E71, m175–m176. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farha, O. K. & Hupp, J. T. (2010). Acc. Chem. Res. 43, 1166–1175. Web of Science CrossRef CAS PubMed Google Scholar
Gao, S., Liu, J.-W., Huo, L.-H., Zhao, H. & Zhao, J.-G. (2004). Acta Cryst. E60, m1875–m1877. Web of Science CSD CrossRef IUCr Journals Google Scholar
Geiger, D. K. (2012). Acta Cryst. E68, m1040. CSD CrossRef IUCr Journals Google Scholar
Geiger, D. K. & Parsons, D. E. (2014). Acta Cryst. E70, m247–m248. CSD CrossRef IUCr Journals Google Scholar
Geiger, D. K., Parsons, D. E. & Zick, P. L. (2014). Acta Cryst. E70, 566–572. CSD CrossRef IUCr Journals Google Scholar
Henehan, C. J., Pountney, D. L., Vašák, M. & Zerbe, O. (1993). Protein Sci. 2, 1756–1764. CrossRef CAS PubMed Google Scholar
Jalilehvand, F., Amini, Z. & Parmar, K. (2012). Inorg. Chem. 51, 10619–10630. Web of Science CrossRef CAS PubMed Google Scholar
Jalilehvand, F., Leung, B. O. & Mah, V. (2009). Inorg. Chem. 48, 5758–5771. Web of Science CrossRef PubMed CAS Google Scholar
Keypour, H., Salehzadeh, S., Pritchard, R. G. & Parish, R. V. (2000). Polyhedron, 19, 1633–1637. Web of Science CSD CrossRef CAS Google Scholar
Kimblin, C. & Parkin, G. (1996). Inorg. Chem. 35, 6912–6913. CSD CrossRef PubMed CAS Web of Science Google Scholar
Kong, Z.-G., Wang, J.-J. & Wang, X.-Y. (2008a). Acta Cryst. C64, m333–m335. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kong, Z.-G., Wang, J.-J. & Wang, X.-Y. (2008b). Acta Cryst. C64, m365–m368. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kreno, L. E., Leong, K., Farha, O. K., Allendorf, M., Van Duyne, R. P. & Hupp, J. T. (2012). Chem. Rev. 112, 1105–1125. Web of Science CrossRef CAS PubMed Google Scholar
Li, Q., Wang, H.-T. & Ye, Q. (2014). Acta Cryst. C70, 992–997. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liang, W.-X. & Qu, Z.-R. (2008). Acta Cryst. E64, m1254. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liu, B.-X. & Xu, D.-J. (2005). Acta Cryst. E61, m1218–m1220. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liu, J.-Q., Zhang, Y., Lü, Y.-J. & Jiang, Z.-J. (2012). Acta Cryst. E68, m430. CSD CrossRef IUCr Journals Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Maxcy, K. R., Smith, R., Willett, R. D. & Vij, A. (2000). Acta Cryst. C56, e454. Web of Science CSD CrossRef IUCr Journals Google Scholar
Mei, L., Li, J., Ming, Z. S., Rong, L. Q. & Liang, L. X. (2009). Russ. J. Coord. Chem. 35, 871–873. Web of Science CrossRef CAS Google Scholar
Muetterties, E. L. & Guggenberger, L. J. (1974). J. Am. Chem. Soc. 96, 1748–1756. CrossRef CAS Web of Science Google Scholar
Narayanan, B. & Bhadbhade, M. M. (1996). Acta Cryst. C52, 3049–3051. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Ovalle-Marroquín, P., Gómez-Lara, J. & Hernández-Ortega, S. (2002). Acta Cryst. E58, m269–m271. Web of Science CSD CrossRef IUCr Journals Google Scholar
Qian, B., Ma, W.-X., Lu, L.-D., Yang, X.-J. & Wang, X. (2007). Acta Cryst. E63, m2930. 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. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Song, W.-D., Gu, C.-S., Liu, J.-W. & Hao, X.-M. (2006). Acta Cryst. E62, m2397–m2399. Web of Science CSD CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Uçar, İ., Yeşilel, O. Z., Bulut, A., İçbudak, H., Ölmez, H. & Kazak, C. (2004). Acta Cryst. C60, m392–m394. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, J., Tao, J.-Q. & Xu, X.-J. (2011). Acta Cryst. C67, m173–m175. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Wang, P., Zhao, Y., Chen, Y. & Kou, X.-Y. (2013). Acta Cryst. C69, 1340–1343. Web of Science CSD CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xu, X.-J., Miao, J.-Y. & Wang, J. (2013). Acta Cryst. C69, 620–623. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhang, X.-F., Gao, S., Huo, L.-H. & Zhao, H. (2007). Acta Cryst. E63, m1314–m1316. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhuo, X., Wang, Z.-W., Li, Y.-Z. & Zheng, H.-G. (2006). Acta Cryst. E62, m785–m787. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zick, P. L. & Geiger, D. K. (2016). Acta Cryst. E72, 1037–1042. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 72| Part 12| December 2016| Pages 1718-1723

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research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Two cadmium coordination polymers with bridging acetate and phenyl­enedi­amine ligands that exhibit two-dimensional layered structures

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

5.1. Preparation of (I)

5.2. Preparation of (II)

6. Refinement

Supporting information

Acknowledgements

References

research communications

Two cadmium coordination polymers with bridging acetate and phenylenediamine ligands that exhibit two-dimensional layered structures

3. Supramolecular features