Crystal structure of bis­(1,3-di­amino­propane-κ2N,N′)bis­[2-(4-nitro­phen­yl)acetato-κO]cadmium

Rahn, I.M.; Crawford, C.L.; Assefa, Z.; Hendrich, J.; Sykora, R.E.

doi:10.1107/S2056989016000943

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 72| Part 2| February 2016| Pages 226-228

doi:10.1107/S2056989016000943

Open

access

Crystal structure of bis(1,3-diaminopropane-κ²N,N′)bis[2-(4-nitrophenyl)acetato-κO]cadmium

Ian M. Rahn,^a Carlos L. Crawford,^b Zerihun Assefa,^b ^* Jeffery Hendrich ^c and Richard E. Sykora ^c

^aUniversity of North Carolina–Chapel Hill, USA, ^b1601 E Market St., Department of Chemistry, North Carolina A&T State University, Greensboro, NC 27411, USA, and ^cUniversity of South Alabama, Department of Chemistry, Mobile, AL 36688-0002, USA
^*Correspondence e-mail: zassefa@ncat.edu

Edited by M. Weil, Vienna University of Technology, Austria (Received 17 December 2015; accepted 15 January 2016; online 23 January 2016)

In the structure of the title compound, [Cd(C₈H₆NO₄)₂(C₃H₁₀N₂)₂], the Cd^II atom is located on a center of symmetry with one independent Cd—O distance of 2.3547 (17) Å and two Cd—N distances of 2.3265 (18) and 2.3449 (19) Å. The Cd^II atom has an overall octahedral coordination environment. Several types of hydrogen-bonding interactions are evident. Both intra- and intermolecular interactions occur between the amino groups and the O atoms of the acetate group. These N—H⋯O hydrogen bonds lead to a layered structure extending parallel to the bc plane. In addition, weak intermolecular C—H⋯O interactions involving the nitro groups exist, leading to the formation of a three-dimensional network structure.

Keywords: crystal structure; cadmium complex; 1,3-diaminopropane; nitrophenylacetic acid.

CCDC reference: 1447705

1. Chemical context

The motivation for this study is based on the desire to expand the crystal engineering aspect of 1,3-diamino propane and carboxylate ligands and enhance their applications in host–guest chemistry (Sundberg et al., 2001 ). It is known that the 1,3-diaminopropane ligand behaves as a strong chelator and forms a stable six-membered ring in its metal complexes as well as being a good hydrogen-bond donor due to the existence of the amino groups (Sundberg et al., 2001). In contrast, the 2-(4-nitrophenyl)acetate ligand has the potential to act as a linker and can also act as a good hydrogen-bond acceptor due to the four oxygen atoms it contains. Combination of these ligands in a single system has the potential to construct hydrogen-bond-directed supramolecular networks. Herein, we report the synthesis and structure of the title compound, [Cd(C₈H₆NO₄)₂(C₃H₁₀N₂)₂], which displays such a hydrogen-bond-directed structure.

2. Structural commentary

As shown in Fig. 1, the Cd^II atom is located on a center of symmetry. Therefore the asymmetric unit consist of half of the molecule. The Cd^II atom is octahedrally coordinated by four N atoms from two diamino propane ligands and two O atoms of monodentate acetate groups from two nitrophenyl-acetate ligands. The diamino propane ligand shows a chelating coordination behavior and displays a chair conformation in the equatorial direction. This kind of coordination mode was also found in other similar complexes (Roberts et al., 2015 ; Sundberg & Uggla, 1997 Sundberg et al., 2001;), although the ligand has also been used as a linker of two metal atoms (Sheng et al., 2014 ). The nitro group is slightly twisted out of the aromatic plane, with a dihedral angle of 3.6 (3)° between the two least-squares planes. A weak intramolecular hydrogen bond of the type N—H⋯O involving one of the amino N atoms of the diaminopropane ligand and the non-coordinating carboxylate O atom of the nitrophenylacetate ligand is evident in the structure at a distance of 3.029 (3) Å (Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2	0.90	2.23	3.029 (3)	147
N2—H2B⋯O2ⁱ	0.90	2.34	3.173 (3)	155
N1—H1A⋯O2ⁱⁱ	0.90	2.29	3.149 (3)	160
C5—H5⋯O4ⁱⁱⁱ	0.93	2.50	3.253 (3)	139
C7—H7⋯O3^iv	0.93	2.57	3.346 (3)	141
C10—H10B⋯O3^v	0.97	2.69	3.629 (3)	163
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{5\over 2}}]$ ; (iv) $[-x+2, y+{\script{1\over 2}}, -z+{\script{5\over 2}}]$ ; (v) x-1, y, z-1.

Figure 1
The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. Non-labelled atoms are generated by the symmetry code −x + 1, −y + 1, −z + 2.

3. Supramolecular features

Somewhat weaker intermolecular N—H⋯O interactions involving the same types of donor and acceptor groups occur between neighboring molecules (Table 1) and lead to a layered arrangement of the molecules parallel to the bc plane (Fig. 2). It should be noted that one of the hydrogen atoms (H1B) of the amino group N1 has no acceptor group in its vicinity; the shortest donor⋯acceptor distance of N1—H1B⋯O2 = 3.868 Å seems to be too long for a significant interaction. Several other weak intermolecular hydrogen-bonding interactions of the C—H⋯O type also exist in the structure involving the O atoms of nitro groups and neighboring C—H groups.

Figure 2
A packing diagram of the title compound. The light-blue dotted lines indicate intramolecular hydrogen-bonding interactions, as well as intralayer interactions involving the nitro groups of adjacent molecules. A weak N—H⋯O interlayer interaction also exists at 3.149 (3) Å, linking the layers (see Table 1

for details).

4. Synthesis and crystallization

0.2 mmol (36.7 mg) of anhydrous CdCl₂, 0.4 mmol (29.7 mg) of 1,3-diaminopropane, and 0.4 mmol (72.5 mg) of 4-nitrophenylacetic acid were added to 2 ml of methanol in a 5 ml beaker. The sample was covered with aluminum foil containing several small vent holes and left for a week to evaporate. The slow evaporation method was used to crystallize a colorless mononuclear species and crystals were gathered for X-ray crystallographic analysis.

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were placed in calculated positions and allowed to ride during subsequent refinement, with U_iso(H) = 1.2U_eq(C) and C—H distances of 0.93 Å for aromatic hydrogen atoms, U_iso(H) = 1.2U_eq(C) and C—H distances of 0.97 Å for methylene hydrogen atoms, and U_iso(H) = 1.2U_eq(N) and N—H distances of 0.90 Å for amino hydrogen atoms.

Table 2
Experimental details

Crystal data
Chemical formula	[Cd(C₈H₆NO₄)₂(C₃H₁₀N₂)₂]
M_r	620.94
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	14.6943 (5), 11.1227 (3), 8.3523 (3)
β (°)	105.778 (4)
V (Å³)	1313.67 (7)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.89
Crystal size (mm)	0.44 × 0.41 × 0.10

Data collection
Diffractometer	Agilent Xcalibur Eos
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2013 )
T_min, T_max	0.923, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9750, 2400, 1911
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.056, 1.06
No. of reflections	2400
No. of parameters	170
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.26
Computer programs: CrysAlis PRO (Agilent, 2013), OLEX2.solve (Bourhis et al., 2015 ), SHELXL97 (Sheldrick, 2008 )and OLEX2 (Dolomanov et al., 2009 ).

Supporting information

CCDC reference: 1447705

Crystal structure: contains datablock I. DOI: 10.1107/S2056989016000943/wm5258sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989016000943/wm5258Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989016000943/wm5258Isup3.cdx

checkCIF report

Chemical context top

The motivation for this study is based on the desire to expand the crystal engineering aspect of 1,3-diamino propane and carboxylate ligands and enhance their applications in host–guest chemistry (Sundberg & Uggla, 2001). It is known that the 1,3-diaminopropane ligand behaves as a strong chelator and forms a stable six-membered ring in its metal complexes as well as being a good hydrogen-bond donor due to the existence of the amino groups (Sundberg & Uggla, 2001). In contrast, the 2-(4-nitrophenyl)acetate ligand has the potential to act as a linker and can also act as a good hydrogen-bond acceptor due to the four oxygen atoms it contains. Combination of these ligands in a single system has the potential to construct hydrogen-bond-directed supramolecular networks. Herein, we report the synthesis and structure of the title compound, [Cd(C₈H₆NO₄)₂(C₃H₁₀N₂)₂], which displays such a hydrogen-bond-directed structure.

Structural commentary top

As shown in Fig. 1, the Cd^II atom is located on a center of symmetry. Therefore the asymmetric unit consist of half of the molecule. The Cd^II atom is octahedrally coordinated by four N atoms from two diamino propane ligands and two O atoms of monodentate acetate groups from two nitrophenyl-acetate ligands. The diamino propane ligand shows a chelating coordination behavior and displays a chair conformation in the equatorial direction. This kind of coordination mode was also found in other similar complexes (Roberts et al., 2015; Sundberg et al., 1997; Sundberg & Uggla, 2001), although the ligand has also been used as a linker of two metal atoms (Sheng et al., 2014). The nitro group is slightly twisted out of the aromatic plane, with a dihedral angle of 3.6 (3)° between the two least-squares planes. A weak intramolecular hydrogen bond of the type N—H···O involving one of the amino N atoms of the diaminopropane ligand and the non-coordinating carboxylate O atom of the nitrophenylacetate ligand is evident in the structure at a distance of 3.029 (3) Å (Table 1).

Supramolecular features top

Somewhat weaker intermolecular N—H···O interactions involving the same types of donor and acceptor groups occur between neighboring molecules (Table 1) lead to a layered arrangement of the molecules parallel to the bc plane (Fig. 2). It should be noted that one of the hydrogen atoms (H1B) of the amino group N1 has no acceptor group in its vicinity; the shortest donor···acceptor distance of N1—H1B···O2 = 3.868 Å seems to be too long for a significant interaction. Several other weak intermolecular hydrogen-bonding interactions of the C—H···O type also exist in the structure involving the O atoms of nitro groups and neighboring C—H groups.

Synthesis and crystallization top

0.2 mmol (36.7 mg) of anhydrous CdCl₂, 0.4 mmol (29.7 mg) of 1,3-diaminopropane, and 0.4 mmol (72.5 mg) of 4-nitrophenylacetic acid were added to 2 ml of methanol in a 5 ml beaker. The sample was covered with aluminium foil containing several small vent holes and left for a week to evaporate. The slow evaporation method was used to crystallize a colorless mononuclear species and crystals were gathered for X-ray crystallographic analysis.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were placed in calculated positions and allowed to ride during subsequent refinement, with U_iso(H) = 1.2U_eq(C) and C—H distances of 0.93 Å for aromatic hydrogen atoms, U_iso(H) = 1.2U_eq(C) and C—H distances of 0.97 Å for secondary methyl hydrogen atoms, and U_iso(H) = 1.2U_eq(N) and N—H distances of 0.90 Å for amino hydrogen atoms.

Structure description top

The motivation for this study is based on the desire to expand the crystal engineering aspect of 1,3-diamino propane and carboxylate ligands and enhance their applications in host–guest chemistry (Sundberg & Uggla, 2001). It is known that the 1,3-diaminopropane ligand behaves as a strong chelator and forms a stable six-membered ring in its metal complexes as well as being a good hydrogen-bond donor due to the existence of the amino groups (Sundberg & Uggla, 2001). In contrast, the 2-(4-nitrophenyl)acetate ligand has the potential to act as a linker and can also act as a good hydrogen-bond acceptor due to the four oxygen atoms it contains. Combination of these ligands in a single system has the potential to construct hydrogen-bond-directed supramolecular networks. Herein, we report the synthesis and structure of the title compound, [Cd(C₈H₆NO₄)₂(C₃H₁₀N₂)₂], which displays such a hydrogen-bond-directed structure.

As shown in Fig. 1, the Cd^II atom is located on a center of symmetry. Therefore the asymmetric unit consist of half of the molecule. The Cd^II atom is octahedrally coordinated by four N atoms from two diamino propane ligands and two O atoms of monodentate acetate groups from two nitrophenyl-acetate ligands. The diamino propane ligand shows a chelating coordination behavior and displays a chair conformation in the equatorial direction. This kind of coordination mode was also found in other similar complexes (Roberts et al., 2015; Sundberg et al., 1997; Sundberg & Uggla, 2001), although the ligand has also been used as a linker of two metal atoms (Sheng et al., 2014). The nitro group is slightly twisted out of the aromatic plane, with a dihedral angle of 3.6 (3)° between the two least-squares planes. A weak intramolecular hydrogen bond of the type N—H···O involving one of the amino N atoms of the diaminopropane ligand and the non-coordinating carboxylate O atom of the nitrophenylacetate ligand is evident in the structure at a distance of 3.029 (3) Å (Table 1).

Synthesis and crystallization top

0.2 mmol (36.7 mg) of anhydrous CdCl₂, 0.4 mmol (29.7 mg) of 1,3-diaminopropane, and 0.4 mmol (72.5 mg) of 4-nitrophenylacetic acid were added to 2 ml of methanol in a 5 ml beaker. The sample was covered with aluminium foil containing several small vent holes and left for a week to evaporate. The slow evaporation method was used to crystallize a colorless mononuclear species and crystals were gathered for X-ray crystallographic analysis.

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were placed in calculated positions and allowed to ride during subsequent refinement, with U_iso(H) = 1.2U_eq(C) and C—H distances of 0.93 Å for aromatic hydrogen atoms, U_iso(H) = 1.2U_eq(C) and C—H distances of 0.97 Å for secondary methyl hydrogen atoms, and U_iso(H) = 1.2U_eq(N) and N—H distances of 0.90 Å for amino hydrogen atoms.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: OLEX2.solve (Bourhis et al., 2015); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. Non-labelled atoms are generated by the symmetry code −x + 1, −y + 1, −z + 2.
	Fig. 2. A packing diagram of the title compound. The light-blue dotted lines indicate intramolecular hydrogen-bonding interactions, as well as intralayer interactions involving the nitro groups of adjacent molecules. A weak N—H···O interlayer interaction also exists at 3.149 (3) Å, linking the layers (see Table 1 for details).

Bis(1,3-diaminopropane-κ²N,N')bis[2-(4-nitrophenyl)acetato-κO]cadmium top

Crystal data top

[Cd(C₈H₆NO₄)₂(C₃H₁₀N₂)₂]	F(000) = 636
M_r = 620.94	D_x = 1.570 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.6943 (5) Å	Cell parameters from 3294 reflections
b = 11.1227 (3) Å	θ = 2.3–27.1°
c = 8.3523 (3) Å	µ = 0.89 mm⁻¹
β = 105.778 (4)°	T = 293 K
V = 1313.67 (7) Å³	Plate, colourless
Z = 2	0.44 × 0.41 × 0.10 mm

Data collection top

Agilent Xcalibur Eos diffractometer	2400 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1911 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 16.0514 pixels mm^-1	θ_max = 25.4°, θ_min = 2.3°
ω scans	h = −17→17
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −12→13
T_min = 0.923, T_max = 1.000	l = −10→10
9750 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.025	H-atom parameters constrained
wR(F²) = 0.056	w = 1/[σ²(F_o²) + (0.0178P)² + 0.5991P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2400 reflections	Δρ_max = 0.27 e Å⁻³
170 parameters	Δρ_min = −0.26 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: iterative	Extinction coefficient: 0.0012 (2)

Crystal data top

[Cd(C₈H₆NO₄)₂(C₃H₁₀N₂)₂]	V = 1313.67 (7) Å³
M_r = 620.94	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.6943 (5) Å	µ = 0.89 mm⁻¹
b = 11.1227 (3) Å	T = 293 K
c = 8.3523 (3) Å	0.44 × 0.41 × 0.10 mm
β = 105.778 (4)°

Data collection top

Agilent Xcalibur Eos diffractometer	2400 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	1911 reflections with I > 2σ(I)
T_min = 0.923, T_max = 1.000	R_int = 0.027
9750 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.056	H-atom parameters constrained
S = 1.06	Δρ_max = 0.27 e Å⁻³
2400 reflections	Δρ_min = −0.26 e Å⁻³
170 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > 2σ(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) top

	x	y	z	U_iso*/U_eq
Cd1	0.5000	0.5000	1.0000	0.03617 (10)
O1	0.62078 (12)	0.49421 (16)	0.8639 (2)	0.0497 (5)
C9	0.30006 (17)	0.5182 (2)	0.7208 (3)	0.0405 (6)
H9A	0.2571	0.5602	0.6291	0.049*
H9B	0.2751	0.5245	0.8167	0.049*
O2	0.57547 (14)	0.35381 (19)	0.6686 (2)	0.0639 (6)
C1	0.63446 (17)	0.4232 (2)	0.7568 (3)	0.0359 (6)
N2	0.44583 (14)	0.31282 (16)	0.8902 (2)	0.0387 (5)
H2A	0.4749	0.2947	0.8113	0.046*
H2B	0.4642	0.2579	0.9717	0.046*
C8	0.84336 (18)	0.5357 (2)	0.9702 (3)	0.0393 (6)
H8	0.8149	0.6073	0.9248	0.047*
C3	0.81242 (16)	0.4281 (2)	0.8897 (3)	0.0339 (5)
C7	0.91540 (18)	0.5390 (2)	1.1161 (3)	0.0386 (6)
H7	0.9355	0.6116	1.1690	0.046*
C6	0.95687 (16)	0.4323 (2)	1.1816 (3)	0.0354 (6)
C4	0.85551 (18)	0.3230 (2)	0.9607 (3)	0.0432 (6)
H4	0.8355	0.2500	0.9089	0.052*
C2	0.73382 (17)	0.4241 (3)	0.7300 (3)	0.0426 (6)
H2C	0.7414	0.3527	0.6682	0.051*
H2D	0.7394	0.4935	0.6628	0.051*
N3	1.03724 (15)	0.4348 (2)	1.3320 (3)	0.0465 (6)
C5	0.92748 (19)	0.3240 (2)	1.1067 (3)	0.0457 (7)
H5	0.9555	0.2526	1.1533	0.055*
C11	0.34305 (18)	0.2995 (2)	0.8167 (3)	0.0502 (7)
H11A	0.3109	0.3124	0.9025	0.060*
H11B	0.3297	0.2180	0.7757	0.060*
C10	0.30436 (19)	0.3869 (2)	0.6752 (3)	0.0482 (7)
H10A	0.3428	0.3806	0.5978	0.058*
H10B	0.2409	0.3613	0.6167	0.058*
O4	1.06568 (14)	0.53165 (17)	1.3946 (2)	0.0551 (5)
O3	1.07278 (16)	0.33928 (19)	1.3882 (3)	0.0844 (8)
N1	0.39369 (14)	0.57670 (19)	0.7594 (2)	0.0432 (5)
H1A	0.3865	0.6561	0.7727	0.052*
H1B	0.4183	0.5668	0.6727	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.02686 (14)	0.03292 (15)	0.04385 (16)	−0.00022 (12)	0.00131 (10)	−0.00811 (12)
O1	0.0383 (10)	0.0604 (12)	0.0531 (11)	−0.0088 (9)	0.0174 (8)	−0.0232 (10)
C9	0.0345 (14)	0.0490 (16)	0.0338 (12)	0.0065 (12)	0.0017 (11)	0.0014 (11)
O2	0.0476 (12)	0.0746 (14)	0.0667 (13)	−0.0169 (11)	0.0109 (10)	−0.0331 (11)
C1	0.0340 (14)	0.0388 (14)	0.0310 (12)	0.0009 (12)	0.0024 (11)	−0.0012 (11)
N2	0.0410 (12)	0.0323 (11)	0.0375 (11)	0.0024 (10)	0.0017 (9)	−0.0008 (9)
C8	0.0380 (14)	0.0317 (13)	0.0472 (15)	0.0046 (11)	0.0097 (12)	0.0054 (11)
C3	0.0278 (12)	0.0433 (14)	0.0331 (12)	−0.0008 (12)	0.0126 (10)	0.0003 (11)
C7	0.0371 (14)	0.0296 (12)	0.0486 (15)	−0.0051 (11)	0.0107 (12)	−0.0057 (11)
C6	0.0300 (13)	0.0364 (14)	0.0388 (13)	−0.0041 (11)	0.0072 (11)	0.0001 (11)
C4	0.0467 (16)	0.0331 (14)	0.0469 (15)	−0.0065 (13)	0.0080 (13)	−0.0086 (12)
C2	0.0382 (15)	0.0568 (17)	0.0345 (13)	0.0017 (14)	0.0126 (11)	−0.0033 (12)
N3	0.0389 (13)	0.0500 (14)	0.0453 (13)	−0.0026 (12)	0.0023 (11)	0.0017 (11)
C5	0.0496 (17)	0.0301 (13)	0.0506 (16)	0.0023 (13)	0.0020 (13)	0.0055 (12)
C11	0.0450 (17)	0.0375 (14)	0.0589 (17)	−0.0096 (13)	−0.0015 (14)	−0.0011 (13)
C10	0.0440 (16)	0.0464 (16)	0.0428 (15)	−0.0008 (13)	−0.0077 (12)	−0.0060 (12)
O4	0.0533 (12)	0.0542 (12)	0.0502 (11)	−0.0163 (10)	0.0013 (9)	−0.0093 (9)
O3	0.0824 (17)	0.0538 (13)	0.0835 (16)	0.0104 (13)	−0.0346 (13)	0.0066 (12)
N1	0.0452 (13)	0.0394 (12)	0.0439 (12)	0.0007 (11)	0.0101 (10)	0.0025 (10)

Geometric parameters (Å, º) top

Cd1—O1ⁱ	2.3547 (17)	C3—C2	1.509 (3)
Cd1—O1	2.3547 (17)	C7—H7	0.9300
Cd1—N2ⁱ	2.3265 (18)	C7—C6	1.377 (3)
Cd1—N2	2.3265 (18)	C6—N3	1.472 (3)
Cd1—N1ⁱ	2.3449 (19)	C6—C5	1.373 (3)
Cd1—N1	2.3449 (19)	C4—H4	0.9300
O1—C1	1.250 (3)	C4—C5	1.379 (3)
C9—H9A	0.9700	C2—H2C	0.9700
C9—H9B	0.9700	C2—H2D	0.9700
C9—C10	1.515 (3)	N3—O4	1.220 (3)
C9—N1	1.476 (3)	N3—O3	1.220 (3)
O2—C1	1.242 (3)	C5—H5	0.9300
C1—C2	1.536 (3)	C11—H11A	0.9700
N2—H2A	0.9000	C11—H11B	0.9700
N2—H2B	0.9000	C11—C10	1.516 (3)
N2—C11	1.475 (3)	C10—H10A	0.9700
C8—H8	0.9300	C10—H10B	0.9700
C8—C3	1.387 (3)	N1—H1A	0.9000
C8—C7	1.380 (3)	N1—H1B	0.9000
C3—C4	1.384 (3)

O1—Cd1—O1ⁱ	180.0	C6—C7—C8	118.6 (2)
N2—Cd1—O1	90.41 (7)	C6—C7—H7	120.7
N2—Cd1—O1ⁱ	89.59 (7)	C7—C6—N3	119.3 (2)
N2ⁱ—Cd1—O1ⁱ	90.41 (7)	C5—C6—C7	121.6 (2)
N2ⁱ—Cd1—O1	89.59 (7)	C5—C6—N3	119.0 (2)
N2—Cd1—N2ⁱ	180.0	C3—C4—H4	119.2
N2—Cd1—N1ⁱ	95.11 (7)	C5—C4—C3	121.6 (2)
N2ⁱ—Cd1—N1	95.11 (7)	C5—C4—H4	119.2
N2ⁱ—Cd1—N1ⁱ	84.89 (7)	C1—C2—H2C	108.8
N2—Cd1—N1	84.89 (7)	C1—C2—H2D	108.8
N1—Cd1—O1ⁱ	89.42 (7)	C3—C2—C1	113.60 (19)
N1ⁱ—Cd1—O1ⁱ	90.58 (7)	C3—C2—H2C	108.8
N1ⁱ—Cd1—O1	89.42 (7)	C3—C2—H2D	108.8
N1—Cd1—O1	90.58 (7)	H2C—C2—H2D	107.7
N1—Cd1—N1ⁱ	180.00 (7)	O4—N3—C6	119.0 (2)
C1—O1—Cd1	130.67 (16)	O4—N3—O3	122.9 (2)
H9A—C9—H9B	107.9	O3—N3—C6	118.2 (2)
C10—C9—H9A	109.1	C6—C5—C4	118.7 (2)
C10—C9—H9B	109.1	C6—C5—H5	120.7
N1—C9—H9A	109.1	C4—C5—H5	120.7
N1—C9—H9B	109.1	N2—C11—H11A	109.1
N1—C9—C10	112.3 (2)	N2—C11—H11B	109.1
O1—C1—C2	116.4 (2)	N2—C11—C10	112.6 (2)
O2—C1—O1	126.5 (2)	H11A—C11—H11B	107.8
O2—C1—C2	117.1 (2)	C10—C11—H11A	109.1
Cd1—N2—H2A	108.0	C10—C11—H11B	109.1
Cd1—N2—H2B	108.0	C9—C10—C11	117.0 (2)
H2A—N2—H2B	107.3	C9—C10—H10A	108.0
C11—N2—Cd1	117.10 (15)	C9—C10—H10B	108.0
C11—N2—H2A	108.0	C11—C10—H10A	108.0
C11—N2—H2B	108.0	C11—C10—H10B	108.0
C3—C8—H8	119.3	H10A—C10—H10B	107.3
C7—C8—H8	119.3	Cd1—N1—H1A	109.0
C7—C8—C3	121.5 (2)	Cd1—N1—H1B	109.0
C8—C3—C2	121.6 (2)	C9—N1—Cd1	113.02 (14)
C4—C3—C8	118.0 (2)	C9—N1—H1A	109.0
C4—C3—C2	120.4 (2)	C9—N1—H1B	109.0
C8—C7—H7	120.7	H1A—N1—H1B	107.8

Cd1—O1—C1—O2	17.7 (4)	C3—C8—C7—C6	0.1 (4)
Cd1—O1—C1—C2	−163.60 (16)	C3—C4—C5—C6	−0.4 (4)
Cd1—N2—C11—C10	58.8 (3)	C7—C8—C3—C4	0.5 (4)
O1ⁱ—Cd1—N2—C11	46.37 (18)	C7—C8—C3—C2	−179.9 (2)
O1—Cd1—N2—C11	−133.63 (18)	C7—C6—N3—O4	−0.5 (4)
O1—Cd1—N1—C9	135.70 (16)	C7—C6—N3—O3	179.8 (3)
O1ⁱ—Cd1—N1—C9	−44.30 (16)	C7—C6—C5—C4	1.0 (4)
O1—C1—C2—C3	43.5 (3)	C4—C3—C2—C1	95.2 (3)
O2—C1—C2—C3	−137.7 (2)	C2—C3—C4—C5	−180.0 (2)
N2ⁱ—Cd1—O1—C1	−170.6 (2)	N3—C6—C5—C4	−176.5 (2)
N2—Cd1—O1—C1	9.4 (2)	C5—C6—N3—O4	177.1 (2)
N2—Cd1—N1—C9	45.35 (16)	C5—C6—N3—O3	−2.6 (4)
N2ⁱ—Cd1—N1—C9	−134.65 (16)	C10—C9—N1—Cd1	−65.9 (2)
N2—C11—C10—C9	−71.0 (3)	N1ⁱ—Cd1—O1—C1	104.5 (2)
C8—C3—C4—C5	−0.3 (4)	N1—Cd1—O1—C1	−75.5 (2)
C8—C3—C2—C1	−84.5 (3)	N1ⁱ—Cd1—N2—C11	136.92 (18)
C8—C7—C6—N3	176.6 (2)	N1—Cd1—N2—C11	−43.08 (18)
C8—C7—C6—C5	−0.8 (4)	N1—C9—C10—C11	76.7 (3)

Symmetry code: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2	0.90	2.23	3.029 (3)	147
N2—H2B···O2ⁱⁱ	0.90	2.34	3.173 (3)	155
N1—H1A···O2ⁱⁱⁱ	0.90	2.29	3.149 (3)	160
C5—H5···O4^iv	0.93	2.50	3.253 (3)	139
C7—H7···O3^v	0.93	2.57	3.346 (3)	141
C10—H10B···O3^vi	0.97	2.69	3.629 (3)	163

Symmetry codes: (ii) x, −y+1/2, z+1/2; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+2, y−1/2, −z+5/2; (v) −x+2, y+1/2, −z+5/2; (vi) x−1, y, z−1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2	0.90	2.23	3.029 (3)	147.0
N2—H2B···O2ⁱ	0.90	2.34	3.173 (3)	154.5
N1—H1A···O2ⁱⁱ	0.90	2.29	3.149 (3)	159.9
C5—H5···O4ⁱⁱⁱ	0.93	2.50	3.253 (3)	138.7
C7—H7···O3^iv	0.93	2.57	3.346 (3)	140.7
C10—H10B···O3^v	0.97	2.69	3.629 (3)	162.8

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, y+1/2, −z+3/2; (iii) −x+2, y−1/2, −z+5/2; (iv) −x+2, y+1/2, −z+5/2; (v) x−1, y, z−1.

Experimental details

Crystal data
Chemical formula	[Cd(C₈H₆NO₄)₂(C₃H₁₀N₂)₂]
M_r	620.94
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	14.6943 (5), 11.1227 (3), 8.3523 (3)
β (°)	105.778 (4)
V (Å³)	1313.67 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.89
Crystal size (mm)	0.44 × 0.41 × 0.10

Data collection
Diffractometer	Agilent Xcalibur Eos
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2013)
T_min, T_max	0.923, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9750, 2400, 1911
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.056, 1.06
No. of reflections	2400
No. of parameters	170
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.26

Computer programs: CrysAlis PRO (Agilent, 2013), OLEX2.solve (Bourhis et al., 2015), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Acknowledgements

ZA acknowledges support from the National Science Foundation, CHE-0959406. Support for the research experience for undergraduate (REU) student (IMR) was provided by NSF-AGS1262876.

References

Agilent (2013). CrysAlis PRO. Agilent Technologies, Yarton, England. Google Scholar
Bourhis, L. J., Dolomanov, O. V., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2015). Acta Cryst. A71, 59–75. Web of Science CrossRef IUCr Journals Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Roberts, T. J., Mehari, T. F., Assefa, Z., Hamby, T. & Sykora, R. E. (2015). Acta Cryst. E71, m240–m241. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheng, G. H., Cheng, X. S., You, Z. L. & Zhu, H. L. (2014). Bull. Chem. Soc. Eth. 28, 315–319. Web of Science CrossRef CAS Google Scholar
Sundberg, M. R., Kivekäs, R., Huovilainen, P. & Uggla, R. (2001). Inorg. Chim. Acta, 324, 212–217. CSD CrossRef CAS Google Scholar
Sundberg, M. R. & Uggla, R. (1997). Inorg. Chim. Acta, 254, 259–265. CSD CrossRef CAS Web of Science Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 72| Part 2| February 2016| Pages 226-228

doi:10.1107/S2056989016000943

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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