metal-organic compounds
Bis(acetato-κO)bis{2-[4-(pyridin-2-yl)phenyl]-1H-imidazo[4,5-f][1,10]phenanthroline-κ2N,N′}cadmium(II)
aSchool of Chemistry and Chemical Engineering, Jiangsu University, 212013 Zhenjiang, Jiangsu, People's Republic of China
*Correspondence e-mail: guoleiqun0606@163.com
The 3COO)(C24H15N5)], comprises one-half of the centrosymmetric molecule. The CdII ion, situated on a centre of inversion, is coordinated by two O atoms from two acetate ligands and four N atoms from two 2-[4-(pyridin-2-yl)phenyl]-1H-imidazo[4,5-f][1,10]phenanthroline (L) ligands in a distorted octahedral geometry. In the L ligand, the terminal phenyl and pyridine rings are turned away from the mean plane of the imidazo[4,5-f][1,10]phenanthroline fragment in opposite directions, at 11.1 (1) and 10.5 (1)°, respectively. In the crystal, N—H⋯O hydrogen bonds link molecules related by translation along the a axis into linear chains, and weak C—H⋯N interactions link these chains into layers parallel to the (011) plane.
of the title compound, [Cd(CHKeywords: crystal structure; CdII complex; hydrogen bonds.
CCDC reference: 885941
Structure description
In recent years, the design and synthesis of novel metal-organic coordination polymers based on 1,10-phenanthroline-derivates ligands have attracted much attention (Wang et al., 2011; Xu et al., 2011; Kong et al., 2015). We report herein the of the title molecular complex (I) (Fig. 1). In (I), the CdII ion, situated on a centre of inversion, is six-coordinated by two O atoms from two acetato ligands and four N atoms from two 2-(4-pyridine-2-yl-phenyl)-1H-imidazo[4,5-f] [1,10]phenanthroline ligands in a distorted octahedral geometry. Such a centrosymmetric coordination of the transition metal atom (Cd) is similar to those observed in the related structures with CCDC refcodes PUPTOK (Wang et al., 2010), WEJLUT (Che, 2006) and WEJNUV (Che et al., 2006). However, all three of the aforementioned compounds are polymeric, while (I) is a 0D molecular complex. In the crystal, the adjacent molecules are linked via N—H⋯O hydrogen bonds (Table 1) into linear chains along the axis a (Fig. 2), and weak C—H⋯N interactions (Table 1) link these chains into layers parallel to the (011) plane.
Synthesis and crystallization
A mixture of Cd(CH3COO)2·4H2O (0.25 mmol), 2-(4-pyridine-2-yl-phenyl)-1H-imidazo[4,5-f][1,10]phenanthroline (0.5 mmol) and H2O (10 ml) was stirred at room temperature for 15 min. When the pH value had been adjusted to about 7.08 with NaOH, the mixture was transferred into a 25 ml Teflon-lined stainless-steel reactor, heated to 453 K for nine days, and then slowly cooled to room temperature at a rate of 5 K h−1. Pale-yellow block crystals of the title complex were isolated, washed with distilled water, and dried in air (yield: 46% based on CdII).
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 885941
10.1107/S2414314616000638/cv4002sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616000638/cv4002Isup2.hkl
A mixture of Cd(CH3COO)2.4H2O (0.25 mmol), 2-(4-pyridine-2-yl-phenyl)-1H- imidazo[4,5-f][1,10]phenanthroline (0.5 mmol) and H2O (10 ml) was stirred at room temperature for 15 min. When the pH value had been adjusted to about 7.08 with NaOH, the mixture was transferred into a 25 ml Teflon-lined stainless-steel reactor, heated to 453 K for nine days, and then slowly cooled to room temperature at a rate of 5 K h−1. Pale-yellow block crystals of the title complex were isolated, washed with distilled water, and dried in air (yield: 46% based on CdII).
In recent years, the design and synthesis of novel metal-organic coordination polymers based on 1,10-phenanthroline-derivates ligands have attracted much attention (Wang et al., 2011; Xu et al., 2011; Kong et al., 2015). We report herein the
of the title molecular complex (I) (Fig. 1). In (I), the CdII ion, situated on a centre of inversion, is six-coordinated by two O atoms from two acetato ligands and four N atoms from two 2-(4-pyridine-2-yl-phenyl)-1H-imidazo[4,5-f] [1,10]phenanthroline ligands in a distorted octahedral geometry. Such a centrosymmetric coordination of the transition metal atom (Cd) is similar to those observed in the related structures with CCDC refcodes PUPTOK (Wang et al., 2010), WEJLUT (Che, 2006) and WEJNUV (Che et al., 2006). However, all three of the aforementioned compounds are polymeric, while (I) is a 0D molecular complex. In the crystal, the adjacent molecules are linked via N—H···O hydrogen bonds (Table 1) into linear chains along the axis a (Fig. 2), and weak C—H···N interactions (Table 1) link these chains into layers parallel to the (011) plane.Data collection: APEX2 (Bruker, 2005); cell
SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. The molecular structure of (I), showing the atomic numbering and 50% probability displacement ellipsoids. [Symmetry code: (A) −x, −y + 1, −z + 1.] | |
Fig. 2. A portion of the crystal packing showing the formation of a hydrogen-bonded (dashed lines) linear chain of molecules. |
[Cd(C2H3O2)(C24H15N5)] | Z = 1 |
Mr = 977.31 | F(000) = 498 |
Triclinic, P1 | Dx = 1.636 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.2984 (12) Å | Cell parameters from 1729 reflections |
b = 9.3261 (14) Å | θ = 2.1–23.6° |
c = 12.5747 (16) Å | µ = 0.62 mm−1 |
α = 107.160 (2)° | T = 293 K |
β = 103.719 (3)° | Block, pale-yellow |
γ = 96.550 (2)° | 0.25 × 0.20 × 0.18 mm |
V = 992.1 (2) Å3 |
Bruker SMART APEX CCD diffractometer | 3448 independent reflections |
Radiation source: fine-focus sealed tube | 3170 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
phi and ω scans | θmax = 25.1°, θmin = 3.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −11→10 |
Tmin = 0.861, Tmax = 0.897 | k = −11→8 |
6876 measured reflections | l = −14→14 |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0696P)2 + 0.0238P] where P = (Fo2 + 2Fc2)/3 |
3448 reflections | (Δ/σ)max < 0.001 |
293 parameters | Δρmax = 1.19 e Å−3 |
0 restraints | Δρmin = −0.95 e Å−3 |
[Cd(C2H3O2)(C24H15N5)] | γ = 96.550 (2)° |
Mr = 977.31 | V = 992.1 (2) Å3 |
Triclinic, P1 | Z = 1 |
a = 9.2984 (12) Å | Mo Kα radiation |
b = 9.3261 (14) Å | µ = 0.62 mm−1 |
c = 12.5747 (16) Å | T = 293 K |
α = 107.160 (2)° | 0.25 × 0.20 × 0.18 mm |
β = 103.719 (3)° |
Bruker SMART APEX CCD diffractometer | 3448 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 3170 reflections with I > 2σ(I) |
Tmin = 0.861, Tmax = 0.897 | Rint = 0.041 |
6876 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.07 | Δρmax = 1.19 e Å−3 |
3448 reflections | Δρmin = −0.95 e Å−3 |
293 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 > σ(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 | ||
C1 | 0.1738 (4) | 0.7815 (5) | 0.7460 (3) | 0.0222 (9) | |
H1 | 0.0793 | 0.8077 | 0.7310 | 0.027* | |
C2 | 0.2863 (4) | 0.8767 (5) | 0.8459 (4) | 0.0260 (9) | |
H2 | 0.2669 | 0.9633 | 0.8957 | 0.031* | |
C3 | 0.4248 (4) | 0.8383 (5) | 0.8677 (3) | 0.0242 (9) | |
H3 | 0.5022 | 0.8992 | 0.9330 | 0.029* | |
C4 | 0.4507 (2) | 0.7022 (2) | 0.78865 (19) | 0.0209 (9) | |
C5 | 0.33294 (19) | 0.6156 (3) | 0.6911 (2) | 0.0193 (8) | |
C6 | 0.3560 (2) | 0.4885 (3) | 0.61043 (17) | 0.0183 (8) | |
C7 | 0.4969 (2) | 0.4479 (2) | 0.62734 (19) | 0.0203 (9) | |
C12 | 0.61462 (19) | 0.5344 (3) | 0.7249 (2) | 0.0199 (8) | |
C11 | 0.5915 (2) | 0.6616 (3) | 0.80555 (17) | 0.0195 (8) | |
C8 | 0.5160 (4) | 0.3161 (5) | 0.5384 (4) | 0.0224 (9) | |
H8 | 0.6090 | 0.2866 | 0.5457 | 0.027* | |
C9 | 0.3958 (4) | 0.2363 (5) | 0.4440 (3) | 0.0232 (9) | |
H9 | 0.4052 | 0.1507 | 0.3871 | 0.028* | |
C10 | 0.2590 (4) | 0.2859 (4) | 0.4350 (4) | 0.0225 (9) | |
H10 | 0.1779 | 0.2311 | 0.3705 | 0.027* | |
C13 | 0.8247 (4) | 0.6499 (5) | 0.8649 (3) | 0.0217 (9) | |
C14 | 0.9828 (4) | 0.6839 (4) | 0.9361 (3) | 0.0210 (9) | |
C15 | 1.0378 (4) | 0.8222 (5) | 1.0267 (3) | 0.0224 (9) | |
H15 | 0.9748 | 0.8921 | 1.0399 | 0.027* | |
C16 | 1.1848 (4) | 0.8580 (5) | 1.0977 (4) | 0.0234 (9) | |
H16 | 1.2201 | 0.9521 | 1.1569 | 0.028* | |
C17 | 1.2810 (4) | 0.7524 (5) | 1.0806 (3) | 0.0207 (9) | |
C18 | 1.2244 (4) | 0.6149 (5) | 0.9902 (4) | 0.0266 (10) | |
H18 | 1.2866 | 0.5440 | 0.9779 | 0.032* | |
C19 | 1.0785 (4) | 0.5791 (5) | 0.9177 (4) | 0.0249 (9) | |
H19 | 1.0442 | 0.4862 | 0.8572 | 0.030* | |
C20 | 1.4371 (4) | 0.7911 (4) | 1.1599 (4) | 0.0222 (9) | |
C21 | 1.5513 (5) | 0.7191 (5) | 1.1270 (4) | 0.0323 (10) | |
H21 | 1.5321 | 0.6469 | 1.0537 | 0.039* | |
C22 | 1.6934 (5) | 0.7574 (5) | 1.2057 (4) | 0.0393 (12) | |
H22 | 1.7704 | 0.7095 | 1.1861 | 0.047* | |
C23 | 1.7198 (4) | 0.8663 (5) | 1.3124 (4) | 0.0303 (10) | |
H23 | 1.8144 | 0.8940 | 1.3666 | 0.036* | |
C24 | 1.6021 (4) | 0.9332 (5) | 1.3369 (4) | 0.0288 (10) | |
H24 | 1.6203 | 1.0082 | 1.4089 | 0.035* | |
C25 | −0.0756 (4) | 0.2401 (5) | 0.5775 (4) | 0.0230 (9) | |
C26 | −0.1180 (5) | 0.1365 (5) | 0.6414 (4) | 0.0304 (10) | |
H26A | −0.1043 | 0.0352 | 0.6042 | 0.046* | |
H26B | −0.2219 | 0.1332 | 0.6405 | 0.046* | |
H26C | −0.0550 | 0.1747 | 0.7202 | 0.046* | |
Cd1 | 0.0000 | 0.5000 | 0.5000 | 0.02133 (17) | |
N1 | 0.1936 (3) | 0.6574 (4) | 0.6721 (3) | 0.0208 (7) | |
N2 | 0.2376 (3) | 0.4062 (4) | 0.5128 (3) | 0.0207 (7) | |
N3 | 0.7245 (3) | 0.7336 (4) | 0.8941 (3) | 0.0218 (7) | |
N4 | 0.7646 (3) | 0.5293 (4) | 0.7644 (3) | 0.0210 (7) | |
H4 | 0.8114 | 0.4627 | 0.7319 | 0.025* | |
N5 | 1.4633 (4) | 0.8975 (4) | 1.2639 (3) | 0.0262 (8) | |
O1 | −0.0839 (3) | 0.3810 (3) | 0.6190 (3) | 0.0278 (7) | |
O2 | −0.0346 (3) | 0.1899 (3) | 0.4899 (3) | 0.0305 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.015 (2) | 0.028 (2) | 0.023 (2) | 0.0088 (16) | 0.0054 (16) | 0.0053 (18) |
C2 | 0.025 (2) | 0.029 (2) | 0.022 (2) | 0.0069 (17) | 0.0051 (17) | 0.0061 (19) |
C3 | 0.021 (2) | 0.026 (2) | 0.018 (2) | −0.0006 (16) | 0.0019 (17) | 0.0011 (18) |
C4 | 0.016 (2) | 0.025 (2) | 0.019 (2) | 0.0031 (15) | 0.0034 (16) | 0.0049 (17) |
C5 | 0.0136 (19) | 0.025 (2) | 0.021 (2) | 0.0060 (15) | 0.0039 (16) | 0.0096 (18) |
C6 | 0.0120 (19) | 0.020 (2) | 0.018 (2) | −0.0010 (14) | 0.0001 (15) | 0.0047 (17) |
C7 | 0.020 (2) | 0.021 (2) | 0.020 (2) | 0.0023 (16) | 0.0056 (16) | 0.0085 (18) |
C12 | 0.016 (2) | 0.022 (2) | 0.020 (2) | 0.0040 (15) | 0.0038 (16) | 0.0065 (17) |
C11 | 0.016 (2) | 0.019 (2) | 0.017 (2) | 0.0006 (15) | 0.0010 (15) | 0.0012 (17) |
C8 | 0.016 (2) | 0.023 (2) | 0.029 (2) | 0.0046 (16) | 0.0053 (17) | 0.0109 (19) |
C9 | 0.021 (2) | 0.019 (2) | 0.023 (2) | 0.0013 (16) | 0.0035 (17) | 0.0012 (17) |
C10 | 0.016 (2) | 0.021 (2) | 0.024 (2) | 0.0012 (16) | 0.0010 (16) | 0.0025 (18) |
C13 | 0.014 (2) | 0.027 (2) | 0.022 (2) | 0.0029 (16) | 0.0019 (16) | 0.0086 (18) |
C14 | 0.019 (2) | 0.021 (2) | 0.022 (2) | 0.0025 (16) | 0.0027 (16) | 0.0081 (18) |
C15 | 0.020 (2) | 0.022 (2) | 0.022 (2) | 0.0074 (16) | 0.0045 (17) | 0.0016 (17) |
C16 | 0.022 (2) | 0.020 (2) | 0.023 (2) | 0.0036 (16) | 0.0030 (17) | 0.0027 (18) |
C17 | 0.017 (2) | 0.024 (2) | 0.020 (2) | 0.0014 (16) | 0.0021 (16) | 0.0084 (18) |
C18 | 0.018 (2) | 0.023 (2) | 0.032 (2) | 0.0061 (16) | 0.0033 (18) | 0.0018 (19) |
C19 | 0.019 (2) | 0.021 (2) | 0.027 (2) | 0.0014 (16) | 0.0006 (18) | 0.0020 (18) |
C20 | 0.021 (2) | 0.019 (2) | 0.023 (2) | 0.0017 (16) | 0.0021 (17) | 0.0060 (18) |
C21 | 0.026 (2) | 0.025 (2) | 0.031 (3) | 0.0032 (18) | 0.0037 (19) | −0.006 (2) |
C22 | 0.016 (2) | 0.032 (3) | 0.051 (3) | 0.0074 (18) | −0.001 (2) | −0.004 (2) |
C23 | 0.014 (2) | 0.031 (3) | 0.037 (3) | 0.0028 (17) | −0.0054 (18) | 0.009 (2) |
C24 | 0.024 (2) | 0.030 (2) | 0.026 (2) | 0.0042 (18) | 0.0007 (18) | 0.0058 (19) |
C25 | 0.0131 (19) | 0.026 (2) | 0.029 (2) | 0.0038 (16) | 0.0024 (17) | 0.0102 (19) |
C26 | 0.029 (2) | 0.030 (2) | 0.031 (2) | 0.0016 (18) | 0.0084 (19) | 0.011 (2) |
Cd1 | 0.0144 (2) | 0.0254 (3) | 0.0198 (3) | 0.00243 (16) | 0.00164 (17) | 0.00412 (19) |
N1 | 0.0151 (17) | 0.0254 (19) | 0.0229 (18) | 0.0072 (13) | 0.0055 (14) | 0.0082 (15) |
N2 | 0.0160 (17) | 0.0210 (18) | 0.0192 (17) | 0.0005 (13) | −0.0011 (13) | 0.0041 (15) |
N3 | 0.0157 (17) | 0.0229 (19) | 0.0191 (18) | 0.0019 (13) | −0.0008 (14) | 0.0012 (15) |
N4 | 0.0181 (17) | 0.0178 (17) | 0.0254 (18) | 0.0095 (13) | 0.0060 (14) | 0.0028 (15) |
N5 | 0.0176 (18) | 0.029 (2) | 0.0263 (19) | 0.0043 (14) | 0.0012 (15) | 0.0050 (16) |
O1 | 0.0246 (15) | 0.0257 (17) | 0.0307 (16) | 0.0052 (12) | 0.0072 (12) | 0.0067 (13) |
O2 | 0.0278 (16) | 0.0359 (18) | 0.0264 (17) | 0.0070 (13) | 0.0086 (13) | 0.0077 (14) |
C1—N1 | 1.316 (5) | C16—C17 | 1.408 (5) |
C1—C2 | 1.402 (5) | C16—H16 | 0.9300 |
C1—H1 | 0.9300 | C17—C18 | 1.384 (6) |
C2—C3 | 1.363 (5) | C17—C20 | 1.488 (5) |
C2—H2 | 0.9300 | C18—C19 | 1.383 (5) |
C3—C4 | 1.448 (4) | C18—H18 | 0.9300 |
C3—H3 | 0.9300 | C19—H19 | 0.9300 |
C4—C5 | 1.3900 | C20—N5 | 1.334 (5) |
C4—C11 | 1.3900 | C20—C21 | 1.398 (6) |
C5—N1 | 1.382 (3) | C21—C22 | 1.384 (6) |
C5—C6 | 1.3900 | C21—H21 | 0.9300 |
C6—N2 | 1.385 (3) | C22—C23 | 1.370 (6) |
C6—C7 | 1.3900 | C22—H22 | 0.9300 |
C7—C12 | 1.3900 | C23—C24 | 1.372 (6) |
C7—C8 | 1.459 (4) | C23—H23 | 0.9300 |
C12—N4 | 1.376 (3) | C24—N5 | 1.334 (5) |
C12—C11 | 1.3900 | C24—H24 | 0.9300 |
C11—N3 | 1.391 (3) | C25—O2 | 1.230 (5) |
C8—C9 | 1.367 (5) | C25—O1 | 1.282 (5) |
C8—H8 | 0.9300 | C25—C26 | 1.503 (6) |
C9—C10 | 1.394 (5) | C26—H26A | 0.9600 |
C9—H9 | 0.9300 | C26—H26B | 0.9600 |
C10—N2 | 1.323 (5) | C26—H26C | 0.9600 |
C10—H10 | 0.9300 | Cd1—O1i | 2.326 (3) |
C13—N3 | 1.331 (5) | Cd1—O1 | 2.326 (3) |
C13—N4 | 1.363 (5) | Cd1—N1 | 2.399 (3) |
C13—C14 | 1.472 (5) | Cd1—N1i | 2.399 (3) |
C14—C15 | 1.389 (5) | Cd1—N2 | 2.455 (3) |
C14—C19 | 1.401 (6) | Cd1—N2i | 2.455 (3) |
C15—C16 | 1.385 (5) | N4—H4 | 0.8600 |
C15—H15 | 0.9300 | ||
N1—C1—C2 | 124.1 (3) | C18—C19—C14 | 119.5 (4) |
N1—C1—H1 | 118.0 | C18—C19—H19 | 120.2 |
C2—C1—H1 | 118.0 | C14—C19—H19 | 120.2 |
C3—C2—C1 | 117.9 (4) | N5—C20—C21 | 121.5 (4) |
C3—C2—H2 | 121.0 | N5—C20—C17 | 117.0 (4) |
C1—C2—H2 | 121.0 | C21—C20—C17 | 121.5 (4) |
C2—C3—C4 | 119.5 (3) | C22—C21—C20 | 118.8 (4) |
C2—C3—H3 | 120.2 | C22—C21—H21 | 120.6 |
C4—C3—H3 | 120.2 | C20—C21—H21 | 120.6 |
C5—C4—C11 | 120.0 | C23—C22—C21 | 119.6 (4) |
C5—C4—C3 | 118.5 (2) | C23—C22—H22 | 120.2 |
C11—C4—C3 | 121.4 (2) | C21—C22—H22 | 120.2 |
N1—C5—C6 | 119.6 (2) | C22—C23—C24 | 117.8 (4) |
N1—C5—C4 | 120.4 (2) | C22—C23—H23 | 121.1 |
C6—C5—C4 | 120.0 | C24—C23—H23 | 121.1 |
N2—C6—C5 | 118.8 (2) | N5—C24—C23 | 124.2 (4) |
N2—C6—C7 | 121.2 (2) | N5—C24—H24 | 117.9 |
C5—C6—C7 | 120.0 | C23—C24—H24 | 117.9 |
C12—C7—C6 | 120.0 | O2—C25—O1 | 122.6 (4) |
C12—C7—C8 | 122.3 (2) | O2—C25—C26 | 120.6 (4) |
C6—C7—C8 | 117.7 (2) | O1—C25—C26 | 116.8 (4) |
N4—C12—C7 | 134.5 (2) | C25—C26—H26A | 109.5 |
N4—C12—C11 | 105.5 (2) | C25—C26—H26B | 109.5 |
C7—C12—C11 | 120.0 | H26A—C26—H26B | 109.5 |
C12—C11—C4 | 120.0 | C25—C26—H26C | 109.5 |
C12—C11—N3 | 110.5 (2) | H26A—C26—H26C | 109.5 |
C4—C11—N3 | 129.4 (2) | H26B—C26—H26C | 109.5 |
C9—C8—C7 | 119.4 (3) | O1i—Cd1—O1 | 180.000 (1) |
C9—C8—H8 | 120.3 | O1i—Cd1—N1 | 93.95 (10) |
C7—C8—H8 | 120.3 | O1—Cd1—N1 | 86.05 (10) |
C8—C9—C10 | 118.6 (4) | O1i—Cd1—N1i | 86.05 (10) |
C8—C9—H9 | 120.7 | O1—Cd1—N1i | 93.95 (10) |
C10—C9—H9 | 120.7 | N1—Cd1—N1i | 180.0 |
N2—C10—C9 | 123.9 (3) | O1i—Cd1—N2 | 83.71 (10) |
N2—C10—H10 | 118.1 | O1—Cd1—N2 | 96.29 (10) |
C9—C10—H10 | 118.1 | N1—Cd1—N2 | 68.72 (10) |
N3—C13—N4 | 113.0 (3) | N1i—Cd1—N2 | 111.28 (10) |
N3—C13—C14 | 122.9 (4) | O1i—Cd1—N2i | 96.29 (10) |
N4—C13—C14 | 124.2 (4) | O1—Cd1—N2i | 83.71 (10) |
C15—C14—C19 | 118.9 (4) | N1—Cd1—N2i | 111.28 (10) |
C15—C14—C13 | 119.0 (4) | N1i—Cd1—N2i | 68.72 (10) |
C19—C14—C13 | 122.1 (4) | N2—Cd1—N2i | 180.000 (1) |
C16—C15—C14 | 121.2 (4) | C1—N1—C5 | 119.5 (3) |
C16—C15—H15 | 119.4 | C1—N1—Cd1 | 123.2 (2) |
C14—C15—H15 | 119.4 | C5—N1—Cd1 | 117.3 (2) |
C15—C16—C17 | 120.2 (4) | C10—N2—C6 | 119.2 (3) |
C15—C16—H16 | 119.9 | C10—N2—Cd1 | 125.2 (2) |
C17—C16—H16 | 119.9 | C6—N2—Cd1 | 115.6 (2) |
C18—C17—C16 | 117.9 (3) | C13—N3—C11 | 104.0 (3) |
C18—C17—C20 | 122.7 (4) | C13—N4—C12 | 107.0 (3) |
C16—C17—C20 | 119.5 (4) | C13—N4—H4 | 126.5 |
C19—C18—C17 | 122.3 (4) | C12—N4—H4 | 126.5 |
C19—C18—H18 | 118.8 | C24—N5—C20 | 118.1 (4) |
C17—C18—H18 | 118.8 | C25—O1—Cd1 | 105.5 (2) |
N1—C1—C2—C3 | 0.0 (6) | C17—C20—C21—C22 | −178.5 (4) |
C1—C2—C3—C4 | −0.3 (6) | C20—C21—C22—C23 | −1.3 (7) |
C2—C3—C4—C5 | 1.1 (5) | C21—C22—C23—C24 | 0.1 (7) |
C2—C3—C4—C11 | 177.9 (3) | C22—C23—C24—N5 | 0.9 (7) |
C11—C4—C5—N1 | −178.4 (3) | C2—C1—N1—C5 | −0.5 (6) |
C3—C4—C5—N1 | −1.5 (3) | C2—C1—N1—Cd1 | −178.7 (3) |
C11—C4—C5—C6 | 0.0 | C6—C5—N1—C1 | −177.1 (3) |
C3—C4—C5—C6 | 176.9 (3) | C4—C5—N1—C1 | 1.2 (4) |
N1—C5—C6—N2 | −0.3 (3) | C6—C5—N1—Cd1 | 1.2 (3) |
C4—C5—C6—N2 | −178.7 (3) | C4—C5—N1—Cd1 | 179.58 (13) |
N1—C5—C6—C7 | 178.4 (3) | O1i—Cd1—N1—C1 | 95.5 (3) |
C4—C5—C6—C7 | 0.0 | O1—Cd1—N1—C1 | −84.5 (3) |
N2—C6—C7—C12 | 178.6 (3) | N2—Cd1—N1—C1 | 177.2 (3) |
C5—C6—C7—C12 | 0.0 | N2i—Cd1—N1—C1 | −2.8 (3) |
N2—C6—C7—C8 | 0.3 (3) | O1i—Cd1—N1—C5 | −82.8 (2) |
C5—C6—C7—C8 | −178.3 (3) | O1—Cd1—N1—C5 | 97.2 (2) |
C6—C7—C12—N4 | −177.2 (3) | N2—Cd1—N1—C5 | −1.1 (2) |
C8—C7—C12—N4 | 1.1 (4) | N2i—Cd1—N1—C5 | 178.9 (2) |
C6—C7—C12—C11 | 0.0 | C9—C10—N2—C6 | −0.9 (6) |
C8—C7—C12—C11 | 178.2 (3) | C9—C10—N2—Cd1 | 179.3 (3) |
N4—C12—C11—C4 | 177.9 (2) | C5—C6—N2—C10 | 179.4 (3) |
C7—C12—C11—C4 | 0.0 | C7—C6—N2—C10 | 0.8 (4) |
N4—C12—C11—N3 | −0.4 (3) | C5—C6—N2—Cd1 | −0.8 (3) |
C7—C12—C11—N3 | −178.3 (2) | C7—C6—N2—Cd1 | −179.40 (13) |
C5—C4—C11—C12 | 0.0 | O1i—Cd1—N2—C10 | −82.5 (3) |
C3—C4—C11—C12 | −176.8 (3) | O1—Cd1—N2—C10 | 97.5 (3) |
C5—C4—C11—N3 | 177.9 (3) | N1—Cd1—N2—C10 | −179.2 (3) |
C3—C4—C11—N3 | 1.2 (3) | N1i—Cd1—N2—C10 | 0.8 (3) |
C12—C7—C8—C9 | −179.6 (3) | O1i—Cd1—N2—C6 | 97.7 (2) |
C6—C7—C8—C9 | −1.3 (4) | O1—Cd1—N2—C6 | −82.3 (2) |
C7—C8—C9—C10 | 1.2 (6) | N1—Cd1—N2—C6 | 1.0 (2) |
C8—C9—C10—N2 | −0.2 (6) | N1i—Cd1—N2—C6 | −179.0 (2) |
N3—C13—C14—C15 | −11.1 (6) | N4—C13—N3—C11 | −0.3 (4) |
N4—C13—C14—C15 | 170.1 (4) | C14—C13—N3—C11 | −179.2 (3) |
N3—C13—C14—C19 | 166.8 (4) | C12—C11—N3—C13 | 0.5 (3) |
N4—C13—C14—C19 | −11.9 (6) | C4—C11—N3—C13 | −177.6 (2) |
C19—C14—C15—C16 | 0.5 (6) | N3—C13—N4—C12 | 0.1 (4) |
C13—C14—C15—C16 | 178.5 (4) | C14—C13—N4—C12 | 178.9 (3) |
C14—C15—C16—C17 | −1.3 (6) | C7—C12—N4—C13 | 177.6 (2) |
C15—C16—C17—C18 | 1.1 (6) | C11—C12—N4—C13 | 0.2 (3) |
C15—C16—C17—C20 | −178.3 (4) | C23—C24—N5—C20 | −0.7 (6) |
C16—C17—C18—C19 | 0.0 (6) | C21—C20—N5—C24 | −0.6 (6) |
C20—C17—C18—C19 | 179.3 (4) | C17—C20—N5—C24 | 179.4 (3) |
C17—C18—C19—C14 | −0.7 (6) | O2—C25—O1—Cd1 | −2.0 (4) |
C15—C14—C19—C18 | 0.5 (6) | C26—C25—O1—Cd1 | 177.7 (3) |
C13—C14—C19—C18 | −177.4 (4) | O1i—Cd1—O1—C25 | 114 (100) |
C18—C17—C20—N5 | −157.8 (4) | N1—Cd1—O1—C25 | −119.9 (2) |
C16—C17—C20—N5 | 21.5 (6) | N1i—Cd1—O1—C25 | 60.1 (2) |
C18—C17—C20—C21 | 22.2 (6) | N2—Cd1—O1—C25 | −51.8 (2) |
C16—C17—C20—C21 | −158.5 (4) | N2i—Cd1—O1—C25 | 128.2 (2) |
N5—C20—C21—C22 | 1.5 (7) |
Symmetry code: (i) −x, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O1ii | 0.86 | 1.93 | 2.724 (4) | 153 |
C9—H9···N5iii | 0.93 | 2.61 | 3.523 (5) | 168 |
Symmetry codes: (ii) x+1, y, z; (iii) x−1, y−1, z−1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O1i | 0.86 | 1.93 | 2.724 (4) | 152.5 |
C9—H9···N5ii | 0.93 | 2.61 | 3.523 (5) | 168.2 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y−1, z−1. |
Experimental details
Crystal data | |
Chemical formula | [Cd(C2H3O2)(C24H15N5)] |
Mr | 977.31 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 9.2984 (12), 9.3261 (14), 12.5747 (16) |
α, β, γ (°) | 107.160 (2), 103.719 (3), 96.550 (2) |
V (Å3) | 992.1 (2) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.62 |
Crystal size (mm) | 0.25 × 0.20 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.861, 0.897 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6876, 3448, 3170 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.122, 1.07 |
No. of reflections | 3448 |
No. of parameters | 293 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.19, −0.95 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008).
Acknowledgements
This work was supported financially by Jiangsu University.
References
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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.
In recent years, the design and synthesis of novel metal-organic coordination polymers based on 1,10-phenanthroline-derivates ligands have attracted much attention (Wang et al., 2011; Xu et al., 2011; Kong et al., 2015). We report herein the crystal structure of the title molecular complex (I) (Fig. 1). In (I), the CdII ion situated on a centre of inversion is six coordinated by two O atoms from two acetato ligands and four N atoms from two 2-(4-pyridine-2-yl-phenyl)-1H-imidazo[4,5-f] [1,10]phenanthroline ligands in a distorted octahedral geometry. Such centrosymmetric coordination of the transition metal atom (Cd) is similar to those observed in the related structures with CCDC refcodes PUPTOK (Wang et al., 2010), WEJLUT (Che, 2006) and WEJNUV (Che et al., 2006). However, all three aforementioned compounds are polymeric, while (I) is 0D molecular complex. In the crystal, the adjacent molecules are linked via N—H···O hydrogen bonds (Table 1) into linear chains along the axis a (Fig. 2), and weak C—H···N interactions (Table 1) link these chains into layers parallel to (011) plane.