research communications
κ2N,N′)bis[2-(4-nitrophenyl)acetato-κO]cadmium
of bis(1,3-diaminopropane-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
In the structure of the title compound, [Cd(C8H6NO4)2(C3H10N2)2], the CdII 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 CdII 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.
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 CdII atom is located on a center of symmetry. Therefore the consist of half of the molecule. The CdII 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).
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.
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 . H atoms were placed in calculated positions and allowed to ride during subsequent with Uiso(H) = 1.2Ueq(C) and C—H distances of 0.93 Å for aromatic hydrogen atoms, Uiso(H) = 1.2Ueq(C) and C—H distances of 0.97 Å for methylene hydrogen atoms, and Uiso(H) = 1.2Ueq(N) and N—H distances of 0.90 Å for amino hydrogen atoms.
details are summarized in Table 2Supporting information
CCDC reference: 1447705
10.1107/S2056989016000943/wm5258sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989016000943/wm5258Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989016000943/wm5258Isup3.cdx
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 CdII atom is located on a center of symmetry. Therefore the
consist of half of the molecule. The CdII 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).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.
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.
Crystal data, data collection and structure
details are summarized in Table 2. H atoms were placed in calculated positions and allowed to ride during subsequent with Uiso(H) = 1.2Ueq(C) and C—H distances of 0.93 Å for aromatic hydrogen atoms, Uiso(H) = 1.2Ueq(C) and C—H distances of 0.97 Å for secondary methyl hydrogen atoms, and Uiso(H) = 1.2Ueq(N) and N—H distances of 0.90 Å for amino hydrogen atoms.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 CdII atom is located on a center of symmetry. Therefore the
consist of half of the molecule. The CdII 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).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.
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.
detailsCrystal data, data collection and structure
details are summarized in Table 2. H atoms were placed in calculated positions and allowed to ride during subsequent with Uiso(H) = 1.2Ueq(C) and C—H distances of 0.93 Å for aromatic hydrogen atoms, Uiso(H) = 1.2Ueq(C) and C—H distances of 0.97 Å for secondary methyl hydrogen atoms, and Uiso(H) = 1.2Ueq(N) and N—H distances of 0.90 Å for amino hydrogen atoms.Data collection: CrysAlis PRO (Agilent, 2013); cell
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).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). |
[Cd(C8H6NO4)2(C3H10N2)2] | F(000) = 636 |
Mr = 620.94 | Dx = 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 |
Agilent Xcalibur Eos diffractometer | 2400 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 1911 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
Detector resolution: 16.0514 pixels mm-1 | θmax = 25.4°, θmin = 2.3° |
ω scans | h = −17→17 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | k = −12→13 |
Tmin = 0.923, Tmax = 1.000 | l = −10→10 |
9750 measured reflections |
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(Fo2) + (0.0178P)2 + 0.5991P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
2400 reflections | Δρmax = 0.27 e Å−3 |
170 parameters | Δρmin = −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) |
[Cd(C8H6NO4)2(C3H10N2)2] | V = 1313.67 (7) Å3 |
Mr = 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)° |
Agilent Xcalibur Eos diffractometer | 2400 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | 1911 reflections with I > 2σ(I) |
Tmin = 0.923, Tmax = 1.000 | Rint = 0.027 |
9750 measured reflections |
R[F2 > 2σ(F2)] = 0.025 | 0 restraints |
wR(F2) = 0.056 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.27 e Å−3 |
2400 reflections | Δρmin = −0.26 e Å−3 |
170 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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. |
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···O4iv | 0.93 | 2.50 | 3.253 (3) | 139 |
C7—H7···O3v | 0.93 | 2.57 | 3.346 (3) | 141 |
C10—H10B···O3vi | 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. |
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···O3iv | 0.93 | 2.57 | 3.346 (3) | 140.7 |
C10—H10B···O3v | 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] |
Mr | 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) |
Tmin, Tmax | 0.923, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9750, 2400, 1911 |
Rint | 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 |
Δρmax, Δρmin (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.