metal-organic compounds
Aquachlorido(4-methylbenzoato-κO)(1,10-phenanthroline-κ2N,N′)copper(II)
aCollege of Science, Guang Dong Ocean University, Zhanjiang 524088, People's Republic of China
*Correspondence e-mail: songwd60@126.com
In the title mononuclear complex, [Cu(C8H7O2)Cl(C12H8N2)(H2O)], the CuII atom is coordinated by one carboxylate O atom from a monodentate 4-methylbenzoate ligand, two N atoms from the 1,10-phenanthroline ligand, one chloride ion and one water molecule in a square-pyramidal geometry. The exhibits inter- and intramolecular C—H⋯Cl, C—H⋯O, O—H⋯Cl and O—H⋯O hydrogen bonds, as well as C—H⋯π interactions of phenanthroline and methyl H atoms towards the π-systems of neighboring 4-methylbenzoate units and the pyridine rings of the phenanthroline system [centroid–centroid distances are 2.706 (2) and 2.992 (1) Å, respectively].
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2004); cell APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536808010945/zl2109sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808010945/zl2109Isup2.hkl
A mixture of copper chloride (1 mmol), 4-methylbenzoic acid (1 mmol), phen (1 mmol), NaOH (1.5 mmol) and H2O (12 ml) was placed in a 23 ml Teflon reactor, which was heated to 433 K for three days and then cooled to room temperature at a rate of 10 K h-1. The crystals obtained were washed with water and dryed in air.
H atoms were placed at calculated positions and were treated as riding on the parent C atoms with C—H = 0.93 - 0.97 Å, N—H = 0.86 Å, and with Uiso(H) = 1.2 Ueq(C, N).
Data collection: APEX2 (Bruker, 2004); cell
APEX2 (Bruker, 2004); data reduction: APEX2 (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: SHELXTL (Sheldrick, 2008\bbr00).Fig. 1. The structure of (I), showing the atomic numbering scheme. Non-H atoms are shown with 30% probability displacement ellipsoids. | |
Fig. 2. A packing view of the title compound. The intermolecluar hydrogen bonds and C—H···π interactions are shown as dashed lines. |
[Cu(C8H7O2)Cl(C12H8N2)(H2O)] | F(000) = 884 |
Mr = 432.35 | Dx = 1.611 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2895 reflections |
a = 10.9095 (4) Å | θ = 2.4–27.9° |
b = 11.0546 (4) Å | µ = 1.40 mm−1 |
c = 15.2059 (6) Å | T = 296 K |
β = 103.578 (2)° | Block, blue |
V = 1782.58 (12) Å3 | 0.30 × 0.29 × 0.25 mm |
Z = 4 |
Bruker APEXII area-detector diffractometer | 4096 independent reflections |
Radiation source: fine-focus sealed tube | 3470 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
ϕ and ω scans | θmax = 27.5°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→14 |
Tmin = 0.679, Tmax = 0.721 | k = −14→14 |
17233 measured reflections | l = −19→19 |
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)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.087 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0424P)2 + 0.6484P] where P = (Fo2 + 2Fc2)/3 |
4096 reflections | (Δ/σ)max = 0.001 |
251 parameters | Δρmax = 0.36 e Å−3 |
3 restraints | Δρmin = −0.41 e Å−3 |
[Cu(C8H7O2)Cl(C12H8N2)(H2O)] | V = 1782.58 (12) Å3 |
Mr = 432.35 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.9095 (4) Å | µ = 1.40 mm−1 |
b = 11.0546 (4) Å | T = 296 K |
c = 15.2059 (6) Å | 0.30 × 0.29 × 0.25 mm |
β = 103.578 (2)° |
Bruker APEXII area-detector diffractometer | 4096 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3470 reflections with I > 2σ(I) |
Tmin = 0.679, Tmax = 0.721 | Rint = 0.039 |
17233 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | 3 restraints |
wR(F2) = 0.087 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.36 e Å−3 |
4096 reflections | Δρmin = −0.41 e Å−3 |
251 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 | 0.64907 (19) | 0.5567 (2) | 0.17000 (14) | 0.0353 (4) | |
H1 | 0.7299 | 0.5880 | 0.1905 | 0.042* | |
C2 | 0.6213 (2) | 0.4448 (2) | 0.20277 (15) | 0.0417 (5) | |
H2 | 0.6826 | 0.4030 | 0.2445 | 0.050* | |
C3 | 0.5034 (2) | 0.3969 (2) | 0.17311 (14) | 0.0401 (5) | |
H3 | 0.4843 | 0.3214 | 0.1934 | 0.048* | |
C4 | 0.41115 (19) | 0.46272 (19) | 0.11182 (13) | 0.0323 (4) | |
C5 | 0.2842 (2) | 0.4229 (2) | 0.07897 (14) | 0.0387 (5) | |
H5 | 0.2592 | 0.3489 | 0.0980 | 0.046* | |
C6 | 0.1996 (2) | 0.4917 (2) | 0.02029 (15) | 0.0396 (5) | |
H6 | 0.1174 | 0.4638 | −0.0003 | 0.047* | |
C7 | 0.23384 (19) | 0.6059 (2) | −0.01065 (14) | 0.0349 (4) | |
C8 | 0.1518 (2) | 0.6819 (2) | −0.07119 (17) | 0.0470 (6) | |
H8 | 0.0687 | 0.6587 | −0.0949 | 0.056* | |
C9 | 0.1943 (2) | 0.7895 (2) | −0.09500 (19) | 0.0541 (7) | |
H9 | 0.1399 | 0.8406 | −0.1345 | 0.065* | |
C10 | 0.3190 (2) | 0.8236 (2) | −0.06052 (16) | 0.0440 (5) | |
H10 | 0.3463 | 0.8979 | −0.0775 | 0.053* | |
C11 | 0.35799 (17) | 0.64676 (18) | 0.02085 (12) | 0.0287 (4) | |
C12 | 0.44711 (17) | 0.57430 (17) | 0.08258 (12) | 0.0276 (4) | |
C13 | 0.85765 (19) | 0.81625 (19) | 0.06922 (14) | 0.0343 (4) | |
C14 | 0.98797 (18) | 0.77868 (18) | 0.11736 (13) | 0.0305 (4) | |
C15 | 1.09054 (19) | 0.8525 (2) | 0.11423 (15) | 0.0375 (5) | |
H15 | 1.0786 | 0.9222 | 0.0790 | 0.045* | |
C16 | 1.20987 (19) | 0.8220 (2) | 0.16345 (15) | 0.0397 (5) | |
H16 | 1.2773 | 0.8727 | 0.1614 | 0.048* | |
C17 | 1.23162 (19) | 0.7185 (2) | 0.21550 (14) | 0.0354 (5) | |
C18 | 1.12943 (19) | 0.6429 (2) | 0.21623 (14) | 0.0364 (5) | |
H18 | 1.1422 | 0.5713 | 0.2492 | 0.044* | |
C19 | 1.00983 (19) | 0.67339 (19) | 0.16855 (14) | 0.0336 (4) | |
H19 | 0.9426 | 0.6226 | 0.1707 | 0.040* | |
C20 | 1.3607 (2) | 0.6881 (3) | 0.27276 (16) | 0.0476 (6) | |
H20A | 1.4229 | 0.7369 | 0.2541 | 0.071* | |
H20B | 1.3784 | 0.6042 | 0.2654 | 0.071* | |
H20C | 1.3629 | 0.7040 | 0.3352 | 0.071* | |
Cl1 | 0.55415 (5) | 0.92640 (5) | 0.16915 (4) | 0.03802 (13) | |
Cu1 | 0.58608 (2) | 0.78128 (2) | 0.052071 (16) | 0.02995 (9) | |
N1 | 0.56500 (14) | 0.62052 (15) | 0.11079 (10) | 0.0290 (3) | |
N2 | 0.40076 (16) | 0.75369 (16) | −0.00414 (12) | 0.0327 (4) | |
O1 | 0.76822 (13) | 0.76408 (14) | 0.09531 (10) | 0.0352 (3) | |
O2 | 0.84387 (16) | 0.8934 (2) | 0.00865 (14) | 0.0697 (6) | |
O1W | 0.60789 (15) | 0.87990 (17) | −0.05137 (12) | 0.0500 (4) | |
H1W | 0.6788 (12) | 0.908 (2) | −0.041 (2) | 0.075* | |
H2W | 0.563 (2) | 0.9330 (19) | −0.0792 (19) | 0.075* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0295 (10) | 0.0428 (12) | 0.0317 (10) | −0.0006 (9) | 0.0034 (8) | 0.0039 (9) |
C2 | 0.0400 (12) | 0.0482 (13) | 0.0348 (11) | 0.0060 (10) | 0.0044 (9) | 0.0126 (10) |
C3 | 0.0479 (13) | 0.0383 (12) | 0.0354 (11) | −0.0028 (10) | 0.0124 (9) | 0.0073 (9) |
C4 | 0.0370 (11) | 0.0319 (10) | 0.0296 (10) | −0.0045 (8) | 0.0112 (8) | −0.0021 (8) |
C5 | 0.0404 (12) | 0.0388 (12) | 0.0390 (11) | −0.0134 (9) | 0.0132 (9) | −0.0029 (9) |
C6 | 0.0306 (10) | 0.0473 (13) | 0.0404 (11) | −0.0141 (9) | 0.0075 (9) | −0.0068 (10) |
C7 | 0.0279 (10) | 0.0428 (12) | 0.0326 (10) | −0.0064 (8) | 0.0042 (8) | −0.0054 (9) |
C8 | 0.0257 (10) | 0.0598 (15) | 0.0492 (13) | −0.0063 (10) | −0.0041 (9) | 0.0032 (12) |
C9 | 0.0348 (12) | 0.0607 (17) | 0.0574 (16) | 0.0031 (11) | −0.0078 (11) | 0.0166 (13) |
C10 | 0.0333 (11) | 0.0433 (12) | 0.0499 (13) | −0.0008 (10) | −0.0013 (10) | 0.0133 (11) |
C11 | 0.0263 (9) | 0.0322 (10) | 0.0271 (9) | −0.0029 (8) | 0.0052 (7) | −0.0023 (8) |
C12 | 0.0267 (9) | 0.0329 (10) | 0.0233 (8) | −0.0032 (8) | 0.0059 (7) | −0.0025 (7) |
C13 | 0.0283 (10) | 0.0372 (11) | 0.0355 (10) | −0.0047 (8) | 0.0037 (8) | 0.0011 (9) |
C14 | 0.0263 (9) | 0.0354 (11) | 0.0295 (10) | −0.0033 (8) | 0.0057 (8) | −0.0034 (8) |
C15 | 0.0316 (10) | 0.0395 (12) | 0.0414 (11) | −0.0053 (9) | 0.0083 (9) | 0.0032 (9) |
C16 | 0.0256 (10) | 0.0486 (13) | 0.0448 (12) | −0.0086 (9) | 0.0080 (9) | −0.0058 (10) |
C17 | 0.0260 (10) | 0.0477 (13) | 0.0317 (10) | 0.0025 (9) | 0.0054 (8) | −0.0089 (9) |
C18 | 0.0342 (11) | 0.0379 (11) | 0.0362 (11) | 0.0036 (9) | 0.0067 (9) | 0.0001 (9) |
C19 | 0.0288 (10) | 0.0360 (11) | 0.0361 (10) | −0.0049 (8) | 0.0081 (8) | −0.0038 (9) |
C20 | 0.0290 (11) | 0.0691 (16) | 0.0419 (12) | 0.0051 (11) | 0.0026 (9) | −0.0065 (12) |
Cl1 | 0.0337 (3) | 0.0380 (3) | 0.0397 (3) | 0.0030 (2) | 0.0033 (2) | 0.0001 (2) |
Cu1 | 0.02281 (13) | 0.03156 (15) | 0.03284 (15) | −0.00285 (9) | 0.00123 (10) | 0.00481 (10) |
N1 | 0.0242 (8) | 0.0334 (9) | 0.0281 (8) | −0.0019 (7) | 0.0035 (6) | 0.0015 (7) |
N2 | 0.0263 (8) | 0.0349 (9) | 0.0335 (9) | −0.0027 (7) | 0.0002 (7) | 0.0022 (7) |
O1 | 0.0234 (7) | 0.0412 (8) | 0.0395 (8) | −0.0019 (6) | 0.0048 (6) | 0.0063 (6) |
O2 | 0.0325 (9) | 0.0915 (15) | 0.0800 (13) | −0.0065 (9) | 0.0027 (9) | 0.0516 (12) |
O1W | 0.0322 (8) | 0.0648 (11) | 0.0498 (10) | 0.0020 (8) | 0.0033 (7) | 0.0280 (9) |
C1—N1 | 1.327 (2) | C13—O2 | 1.238 (3) |
C1—C2 | 1.394 (3) | C13—O1 | 1.274 (2) |
C1—H1 | 0.9300 | C13—C14 | 1.497 (3) |
C2—C3 | 1.366 (3) | C14—C19 | 1.389 (3) |
C2—H2 | 0.9300 | C14—C15 | 1.395 (3) |
C3—C4 | 1.403 (3) | C15—C16 | 1.382 (3) |
C3—H3 | 0.9300 | C15—H15 | 0.9300 |
C4—C12 | 1.398 (3) | C16—C17 | 1.381 (3) |
C4—C5 | 1.427 (3) | C16—H16 | 0.9300 |
C5—C6 | 1.356 (3) | C17—C18 | 1.395 (3) |
C5—H5 | 0.9300 | C17—C20 | 1.509 (3) |
C6—C7 | 1.428 (3) | C18—C19 | 1.377 (3) |
C6—H6 | 0.9300 | C18—H18 | 0.9300 |
C7—C11 | 1.401 (3) | C19—H19 | 0.9300 |
C7—C8 | 1.403 (3) | C20—H20A | 0.9600 |
C8—C9 | 1.356 (3) | C20—H20B | 0.9600 |
C8—H8 | 0.9300 | C20—H20C | 0.9600 |
C9—C10 | 1.390 (3) | Cl1—Cu1 | 2.4810 (6) |
C9—H9 | 0.9300 | Cu1—O1 | 1.9503 (14) |
C10—N2 | 1.330 (3) | Cu1—O1W | 1.9736 (16) |
C10—H10 | 0.9300 | Cu1—N2 | 2.0248 (17) |
C11—N2 | 1.357 (3) | Cu1—N1 | 2.0261 (17) |
C11—C12 | 1.428 (3) | O1W—H1W | 0.812 (10) |
C12—N1 | 1.357 (2) | O1W—H2W | 0.816 (10) |
N1—C1—C2 | 122.73 (19) | C16—C15—C14 | 120.0 (2) |
N1—C1—H1 | 118.6 | C16—C15—H15 | 120.0 |
C2—C1—H1 | 118.6 | C14—C15—H15 | 120.0 |
C3—C2—C1 | 119.5 (2) | C17—C16—C15 | 121.7 (2) |
C3—C2—H2 | 120.2 | C17—C16—H16 | 119.1 |
C1—C2—H2 | 120.2 | C15—C16—H16 | 119.1 |
C2—C3—C4 | 119.4 (2) | C16—C17—C18 | 118.09 (19) |
C2—C3—H3 | 120.3 | C16—C17—C20 | 121.8 (2) |
C4—C3—H3 | 120.3 | C18—C17—C20 | 120.1 (2) |
C12—C4—C3 | 117.22 (18) | C19—C18—C17 | 120.6 (2) |
C12—C4—C5 | 118.85 (19) | C19—C18—H18 | 119.7 |
C3—C4—C5 | 123.92 (19) | C17—C18—H18 | 119.7 |
C6—C5—C4 | 120.8 (2) | C18—C19—C14 | 121.09 (19) |
C6—C5—H5 | 119.6 | C18—C19—H19 | 119.5 |
C4—C5—H5 | 119.6 | C14—C19—H19 | 119.5 |
C5—C6—C7 | 121.51 (19) | C17—C20—H20A | 109.5 |
C5—C6—H6 | 119.2 | C17—C20—H20B | 109.5 |
C7—C6—H6 | 119.2 | H20A—C20—H20B | 109.5 |
C11—C7—C8 | 116.6 (2) | C17—C20—H20C | 109.5 |
C11—C7—C6 | 118.62 (19) | H20A—C20—H20C | 109.5 |
C8—C7—C6 | 124.78 (19) | H20B—C20—H20C | 109.5 |
C9—C8—C7 | 119.7 (2) | O1—Cu1—O1W | 91.07 (6) |
C9—C8—H8 | 120.2 | O1—Cu1—N2 | 164.79 (7) |
C7—C8—H8 | 120.2 | O1W—Cu1—N2 | 92.41 (7) |
C8—C9—C10 | 120.2 (2) | O1—Cu1—N1 | 88.73 (6) |
C8—C9—H9 | 119.9 | O1W—Cu1—N1 | 152.03 (8) |
C10—C9—H9 | 119.9 | N2—Cu1—N1 | 81.29 (7) |
N2—C10—C9 | 122.3 (2) | O1—Cu1—Cl1 | 97.16 (5) |
N2—C10—H10 | 118.9 | O1W—Cu1—Cl1 | 106.16 (6) |
C9—C10—H10 | 118.9 | N2—Cu1—Cl1 | 96.07 (5) |
N2—C11—C7 | 123.57 (18) | N1—Cu1—Cl1 | 101.62 (5) |
N2—C11—C12 | 116.53 (16) | C1—N1—C12 | 117.86 (17) |
C7—C11—C12 | 119.89 (18) | C1—N1—Cu1 | 129.28 (14) |
N1—C12—C4 | 123.21 (18) | C12—N1—Cu1 | 112.85 (12) |
N1—C12—C11 | 116.44 (17) | C10—N2—C11 | 117.66 (18) |
C4—C12—C11 | 120.35 (17) | C10—N2—Cu1 | 129.52 (15) |
O2—C13—O1 | 125.12 (19) | C11—N2—Cu1 | 112.82 (13) |
O2—C13—C14 | 119.36 (18) | C13—O1—Cu1 | 130.15 (14) |
O1—C13—C14 | 115.52 (18) | Cu1—O1W—H1W | 110 (2) |
C19—C14—C15 | 118.41 (19) | Cu1—O1W—H2W | 130 (2) |
C19—C14—C13 | 121.65 (18) | H1W—O1W—H2W | 105.0 (15) |
C15—C14—C13 | 119.90 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···Cl1i | 0.93 | 2.76 | 3.654 (2) | 162 |
C1—H1···O1 | 0.93 | 2.52 | 2.988 (3) | 112 |
O1W—H2W···Cl1i | 0.82 (1) | 2.26 (1) | 3.0709 (17) | 174 (3) |
O1W—H1W···O2 | 0.81 (1) | 1.79 (1) | 2.526 (2) | 150 (3) |
C3—H3···Cg1ii | 0.93 | 2.71 | 3.413 (2) | 133 |
C20—H20B···Cg2iii | 0.93 | 2.99 | 3.627 (2) | 125 |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+3/2, y−1/2, −z+1/2; (iii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | [Cu(C8H7O2)Cl(C12H8N2)(H2O)] |
Mr | 432.35 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 296 |
a, b, c (Å) | 10.9095 (4), 11.0546 (4), 15.2059 (6) |
β (°) | 103.578 (2) |
V (Å3) | 1782.58 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.40 |
Crystal size (mm) | 0.30 × 0.29 × 0.25 |
Data collection | |
Diffractometer | Bruker APEXII area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.679, 0.721 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17233, 4096, 3470 |
Rint | 0.039 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.087, 1.05 |
No. of reflections | 4096 |
No. of parameters | 251 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.36, −0.41 |
Computer programs: APEX2 (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2001), SHELXTL (Sheldrick, 2008\bbr00).
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···Cl1i | 0.93 | 2.76 | 3.654 (2) | 162.0 |
C1—H1···O1 | 0.93 | 2.52 | 2.988 (3) | 111.6 |
O1W—H2W···Cl1i | 0.816 (10) | 2.259 (10) | 3.0709 (17) | 174 (3) |
O1W—H1W···O2 | 0.812 (10) | 1.788 (14) | 2.526 (2) | 150 (3) |
C3—H3···Cg1ii | 0.93 | 2.71 | 3.413 (2) | 133 |
C20—H20B···Cg2iii | 0.93 | 2.99 | 3.627 (2) | 125 |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+3/2, y−1/2, −z+1/2; (iii) x+1, y, z. |
Acknowledgements
The authors acknowledge Guang Dong Ocean University for supporting this work.
References
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Song, W.-D., Gu, C.-S., Hao, X.-M. & Liu, J.-W. (2007). Acta Cryst. E63, m1023–m1024. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
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In the structural investigation of 4-methylbenzoate complexes, it has been found that the 4-methylbenzoic acid functions as a multidentate ligand [Song et al. (2007)], with versatile binding and coordination modes. In this paper, we report the crystal structure of the title compound, (I), a new Cu complex obtained by the reaction of 4-methylbenzoic acid, 1,10-phenanthroline and copper chloride in an alkaline aqueous solution.
As illustrated in Figure 1, the CuII atom exists in a square pyramidal environment, defined by one carboxyl O atom from a monodentate 4-methylbenzate ligand, two N atoms from the 1,10-phenanthroline ligand, one chlorine ion and a water molecule. The crystal structure exhibits inter and intramolecular C—H···Cl, C—H···O, O—H···Cl and O—H···O hydrogen bonding and C—H···π interactions of phenanthroline and methyl H atoms towards the π-systems of neighboring 4-methylbenzate units and of pyridine rings of the phenanthroline system. Centroid to centroid distances are 2.706 (2)Å and 2.992 (1) Å, respectively. (Table 1, Fig. 2, Cg1 = Ring (C14-C19) ; Cg2 = Ring (C1-C4 ,C12, N1)).