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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 72| Part 2| February 2016| Pages 226-228

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

CROSSMARK_Color_square_no_text.svg

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 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.

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[Sundberg, M. R., Kivekäs, R., Huovilainen, P. & Uggla, R. (2001). Inorg. Chim. Acta, 324, 212-217.]). 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[Sundberg, M. R., Kivekäs, R., Huovilainen, P. & Uggla, R. (2001). Inorg. Chim. Acta, 324, 212-217.]). 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.

[Scheme 1]

2. Structural commentary

As shown in Fig. 1[link], the CdII atom is located on a center of symmetry. Therefore the asymmetric unit 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[Roberts, T. J., Mehari, T. F., Assefa, Z., Hamby, T. & Sykora, R. E. (2015). Acta Cryst. E71, m240-m241.]; Sundberg & Uggla, 1997[Sundberg, M. R. & Uggla, R. (1997). Inorg. Chim. Acta, 254, 259-265.] Sundberg et al., 2001[Sundberg, M. R., Kivekäs, R., Huovilainen, P. & Uggla, R. (2001). Inorg. Chim. Acta, 324, 212-217.];), although the ligand has also been used as a linker of two metal atoms (Sheng et al., 2014[Sheng, G. H., Cheng, X. S., You, Z. L. & Zhu, H. L. (2014). Bull. Chem. Soc. Eth. 28, 315-319.]). 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[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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⋯O3iv 0.93 2.57 3.346 (3) 141
C10—H10B⋯O3v 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]
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[link]) and lead to a layered arrangement of the mol­ecules parallel to the bc plane (Fig. 2[link]). 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]
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[link] 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[link]. H atoms were placed in calculated positions and allowed to ride during subsequent refinement, 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.

Table 2
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)
V3) 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[Agilent (2013). CrysAlis PRO. Agilent Technologies, Yarton, England.])
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−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[Agilent (2013). CrysAlis PRO. Agilent Technologies, Yarton, England.]), OLEX2.solve (Bourhis et al., 2015[Bourhis, L. J., Dolomanov, O. V., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2015). Acta Cryst. A71, 59-75.]), SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.])and OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

Supporting information


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 CdII atom is located on a center of symmetry. Therefore the asymmetric unit 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).

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 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.

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 CdII atom is located on a center of symmetry. Therefore the asymmetric unit 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.

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 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.

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
[Figure 1] 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.
[Figure 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
Mr = 620.94Dx = 1.570 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 14.6943 (5) ÅCell parameters from 3294 reflections
b = 11.1227 (3) Åθ = 2.3–27.1°
c = 8.3523 (3) ŵ = 0.89 mm1
β = 105.778 (4)°T = 293 K
V = 1313.67 (7) Å3Plate, colourless
Z = 20.44 × 0.41 × 0.10 mm
Data collection top
Agilent Xcalibur Eos
diffractometer
2400 independent reflections
Radiation source: Enhance (Mo) X-ray Source1911 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
Detector resolution: 16.0514 pixels mm-1θmax = 25.4°, θmin = 2.3°
ω scansh = 1717
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
k = 1213
Tmin = 0.923, Tmax = 1.000l = 1010
9750 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025H-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 reflectionsΔρmax = 0.27 e Å3
170 parametersΔρmin = 0.26 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: iterativeExtinction coefficient: 0.0012 (2)
Crystal data top
[Cd(C8H6NO4)2(C3H10N2)2]V = 1313.67 (7) Å3
Mr = 620.94Z = 2
Monoclinic, P21/cMo Kα radiation
a = 14.6943 (5) ŵ = 0.89 mm1
b = 11.1227 (3) ÅT = 293 K
c = 8.3523 (3) Å0.44 × 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)
Tmin = 0.923, Tmax = 1.000Rint = 0.027
9750 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0250 restraints
wR(F2) = 0.056H-atom parameters constrained
S = 1.06Δρmax = 0.27 e Å3
2400 reflectionsΔρmin = 0.26 e Å3
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
xyzUiso*/Ueq
Cd10.50000.50001.00000.03617 (10)
O10.62078 (12)0.49421 (16)0.8639 (2)0.0497 (5)
C90.30006 (17)0.5182 (2)0.7208 (3)0.0405 (6)
H9A0.25710.56020.62910.049*
H9B0.27510.52450.81670.049*
O20.57547 (14)0.35381 (19)0.6686 (2)0.0639 (6)
C10.63446 (17)0.4232 (2)0.7568 (3)0.0359 (6)
N20.44583 (14)0.31282 (16)0.8902 (2)0.0387 (5)
H2A0.47490.29470.81130.046*
H2B0.46420.25790.97170.046*
C80.84336 (18)0.5357 (2)0.9702 (3)0.0393 (6)
H80.81490.60730.92480.047*
C30.81242 (16)0.4281 (2)0.8897 (3)0.0339 (5)
C70.91540 (18)0.5390 (2)1.1161 (3)0.0386 (6)
H70.93550.61161.16900.046*
C60.95687 (16)0.4323 (2)1.1816 (3)0.0354 (6)
C40.85551 (18)0.3230 (2)0.9607 (3)0.0432 (6)
H40.83550.25000.90890.052*
C20.73382 (17)0.4241 (3)0.7300 (3)0.0426 (6)
H2C0.74140.35270.66820.051*
H2D0.73940.49350.66280.051*
N31.03724 (15)0.4348 (2)1.3320 (3)0.0465 (6)
C50.92748 (19)0.3240 (2)1.1067 (3)0.0457 (7)
H50.95550.25261.15330.055*
C110.34305 (18)0.2995 (2)0.8167 (3)0.0502 (7)
H11A0.31090.31240.90250.060*
H11B0.32970.21800.77570.060*
C100.30436 (19)0.3869 (2)0.6752 (3)0.0482 (7)
H10A0.34280.38060.59780.058*
H10B0.24090.36130.61670.058*
O41.06568 (14)0.53165 (17)1.3946 (2)0.0551 (5)
O31.07278 (16)0.33928 (19)1.3882 (3)0.0844 (8)
N10.39369 (14)0.57670 (19)0.7594 (2)0.0432 (5)
H1A0.38650.65610.77270.052*
H1B0.41830.56680.67270.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.02686 (14)0.03292 (15)0.04385 (16)0.00022 (12)0.00131 (10)0.00811 (12)
O10.0383 (10)0.0604 (12)0.0531 (11)0.0088 (9)0.0174 (8)0.0232 (10)
C90.0345 (14)0.0490 (16)0.0338 (12)0.0065 (12)0.0017 (11)0.0014 (11)
O20.0476 (12)0.0746 (14)0.0667 (13)0.0169 (11)0.0109 (10)0.0331 (11)
C10.0340 (14)0.0388 (14)0.0310 (12)0.0009 (12)0.0024 (11)0.0012 (11)
N20.0410 (12)0.0323 (11)0.0375 (11)0.0024 (10)0.0017 (9)0.0008 (9)
C80.0380 (14)0.0317 (13)0.0472 (15)0.0046 (11)0.0097 (12)0.0054 (11)
C30.0278 (12)0.0433 (14)0.0331 (12)0.0008 (12)0.0126 (10)0.0003 (11)
C70.0371 (14)0.0296 (12)0.0486 (15)0.0051 (11)0.0107 (12)0.0057 (11)
C60.0300 (13)0.0364 (14)0.0388 (13)0.0041 (11)0.0072 (11)0.0001 (11)
C40.0467 (16)0.0331 (14)0.0469 (15)0.0065 (13)0.0080 (13)0.0086 (12)
C20.0382 (15)0.0568 (17)0.0345 (13)0.0017 (14)0.0126 (11)0.0033 (12)
N30.0389 (13)0.0500 (14)0.0453 (13)0.0026 (12)0.0023 (11)0.0017 (11)
C50.0496 (17)0.0301 (13)0.0506 (16)0.0023 (13)0.0020 (13)0.0055 (12)
C110.0450 (17)0.0375 (14)0.0589 (17)0.0096 (13)0.0015 (14)0.0011 (13)
C100.0440 (16)0.0464 (16)0.0428 (15)0.0008 (13)0.0077 (12)0.0060 (12)
O40.0533 (12)0.0542 (12)0.0502 (11)0.0163 (10)0.0013 (9)0.0093 (9)
O30.0824 (17)0.0538 (13)0.0835 (16)0.0104 (13)0.0346 (13)0.0066 (12)
N10.0452 (13)0.0394 (12)0.0439 (12)0.0007 (11)0.0101 (10)0.0025 (10)
Geometric parameters (Å, º) top
Cd1—O1i2.3547 (17)C3—C21.509 (3)
Cd1—O12.3547 (17)C7—H70.9300
Cd1—N2i2.3265 (18)C7—C61.377 (3)
Cd1—N22.3265 (18)C6—N31.472 (3)
Cd1—N1i2.3449 (19)C6—C51.373 (3)
Cd1—N12.3449 (19)C4—H40.9300
O1—C11.250 (3)C4—C51.379 (3)
C9—H9A0.9700C2—H2C0.9700
C9—H9B0.9700C2—H2D0.9700
C9—C101.515 (3)N3—O41.220 (3)
C9—N11.476 (3)N3—O31.220 (3)
O2—C11.242 (3)C5—H50.9300
C1—C21.536 (3)C11—H11A0.9700
N2—H2A0.9000C11—H11B0.9700
N2—H2B0.9000C11—C101.516 (3)
N2—C111.475 (3)C10—H10A0.9700
C8—H80.9300C10—H10B0.9700
C8—C31.387 (3)N1—H1A0.9000
C8—C71.380 (3)N1—H1B0.9000
C3—C41.384 (3)
O1—Cd1—O1i180.0C6—C7—C8118.6 (2)
N2—Cd1—O190.41 (7)C6—C7—H7120.7
N2—Cd1—O1i89.59 (7)C7—C6—N3119.3 (2)
N2i—Cd1—O1i90.41 (7)C5—C6—C7121.6 (2)
N2i—Cd1—O189.59 (7)C5—C6—N3119.0 (2)
N2—Cd1—N2i180.0C3—C4—H4119.2
N2—Cd1—N1i95.11 (7)C5—C4—C3121.6 (2)
N2i—Cd1—N195.11 (7)C5—C4—H4119.2
N2i—Cd1—N1i84.89 (7)C1—C2—H2C108.8
N2—Cd1—N184.89 (7)C1—C2—H2D108.8
N1—Cd1—O1i89.42 (7)C3—C2—C1113.60 (19)
N1i—Cd1—O1i90.58 (7)C3—C2—H2C108.8
N1i—Cd1—O189.42 (7)C3—C2—H2D108.8
N1—Cd1—O190.58 (7)H2C—C2—H2D107.7
N1—Cd1—N1i180.00 (7)O4—N3—C6119.0 (2)
C1—O1—Cd1130.67 (16)O4—N3—O3122.9 (2)
H9A—C9—H9B107.9O3—N3—C6118.2 (2)
C10—C9—H9A109.1C6—C5—C4118.7 (2)
C10—C9—H9B109.1C6—C5—H5120.7
N1—C9—H9A109.1C4—C5—H5120.7
N1—C9—H9B109.1N2—C11—H11A109.1
N1—C9—C10112.3 (2)N2—C11—H11B109.1
O1—C1—C2116.4 (2)N2—C11—C10112.6 (2)
O2—C1—O1126.5 (2)H11A—C11—H11B107.8
O2—C1—C2117.1 (2)C10—C11—H11A109.1
Cd1—N2—H2A108.0C10—C11—H11B109.1
Cd1—N2—H2B108.0C9—C10—C11117.0 (2)
H2A—N2—H2B107.3C9—C10—H10A108.0
C11—N2—Cd1117.10 (15)C9—C10—H10B108.0
C11—N2—H2A108.0C11—C10—H10A108.0
C11—N2—H2B108.0C11—C10—H10B108.0
C3—C8—H8119.3H10A—C10—H10B107.3
C7—C8—H8119.3Cd1—N1—H1A109.0
C7—C8—C3121.5 (2)Cd1—N1—H1B109.0
C8—C3—C2121.6 (2)C9—N1—Cd1113.02 (14)
C4—C3—C8118.0 (2)C9—N1—H1A109.0
C4—C3—C2120.4 (2)C9—N1—H1B109.0
C8—C7—H7120.7H1A—N1—H1B107.8
Cd1—O1—C1—O217.7 (4)C3—C8—C7—C60.1 (4)
Cd1—O1—C1—C2163.60 (16)C3—C4—C5—C60.4 (4)
Cd1—N2—C11—C1058.8 (3)C7—C8—C3—C40.5 (4)
O1i—Cd1—N2—C1146.37 (18)C7—C8—C3—C2179.9 (2)
O1—Cd1—N2—C11133.63 (18)C7—C6—N3—O40.5 (4)
O1—Cd1—N1—C9135.70 (16)C7—C6—N3—O3179.8 (3)
O1i—Cd1—N1—C944.30 (16)C7—C6—C5—C41.0 (4)
O1—C1—C2—C343.5 (3)C4—C3—C2—C195.2 (3)
O2—C1—C2—C3137.7 (2)C2—C3—C4—C5180.0 (2)
N2i—Cd1—O1—C1170.6 (2)N3—C6—C5—C4176.5 (2)
N2—Cd1—O1—C19.4 (2)C5—C6—N3—O4177.1 (2)
N2—Cd1—N1—C945.35 (16)C5—C6—N3—O32.6 (4)
N2i—Cd1—N1—C9134.65 (16)C10—C9—N1—Cd165.9 (2)
N2—C11—C10—C971.0 (3)N1i—Cd1—O1—C1104.5 (2)
C8—C3—C4—C50.3 (4)N1—Cd1—O1—C175.5 (2)
C8—C3—C2—C184.5 (3)N1i—Cd1—N2—C11136.92 (18)
C8—C7—C6—N3176.6 (2)N1—Cd1—N2—C1143.08 (18)
C8—C7—C6—C50.8 (4)N1—C9—C10—C1176.7 (3)
Symmetry code: (i) x+1, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O20.902.233.029 (3)147
N2—H2B···O2ii0.902.343.173 (3)155
N1—H1A···O2iii0.902.293.149 (3)160
C5—H5···O4iv0.932.503.253 (3)139
C7—H7···O3v0.932.573.346 (3)141
C10—H10B···O3vi0.972.693.629 (3)163
Symmetry codes: (ii) x, y+1/2, z+1/2; (iii) x+1, y+1/2, z+3/2; (iv) x+2, y1/2, z+5/2; (v) x+2, y+1/2, z+5/2; (vi) x1, y, z1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O20.902.233.029 (3)147.0
N2—H2B···O2i0.902.343.173 (3)154.5
N1—H1A···O2ii0.902.293.149 (3)159.9
C5—H5···O4iii0.932.503.253 (3)138.7
C7—H7···O3iv0.932.573.346 (3)140.7
C10—H10B···O3v0.972.693.629 (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, y1/2, z+5/2; (iv) x+2, y+1/2, z+5/2; (v) x1, y, z1.

Experimental details

Crystal data
Chemical formula[Cd(C8H6NO4)2(C3H10N2)2]
Mr620.94
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)14.6943 (5), 11.1227 (3), 8.3523 (3)
β (°) 105.778 (4)
V3)1313.67 (7)
Z2
Radiation typeMo Kα
µ (mm1)0.89
Crystal size (mm)0.44 × 0.41 × 0.10
Data collection
DiffractometerAgilent Xcalibur Eos
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2013)
Tmin, Tmax0.923, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
9750, 2400, 1911
Rint0.027
(sin θ/λ)max1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.025, 0.056, 1.06
No. of reflections2400
No. of parameters170
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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

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