metal-organic compounds
(2,2′-Bipyridyl-κ2N,N′)tetrakis(4-methylbenzoato-κO)manganese(II)
aCollege of Science, Guang Dong Ocean University, Zhan Jiang 524088, People's Republic of China, and bCollege of Chemistry, South China University of Technology, Guangzhou 510640, People's Republic of China
*Correspondence e-mail: songwd60@126.com
In the title mononuclear complex, [Mn(C8H7O2)4(C10H8N2)], the MnII atom lies on a twofold rotation axis and has a distorted octahedral coordination geometry defined by four O atoms from four 4-methylbenzoate ligands and two N atoms from one 2,2′-bipyridyl ligand. The is stabilized by intermolecular hydrogen bonds and π–π stacking interactions [the centroid–centroid distance between the parallel pyridyl ring of a 2,2′-bipyridyl and benzene ring of a 4-methylbenzoic group of a neighboring complex is 3.839 (2) Å].
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2004); cell SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S160053680800994X/bg2175sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053680800994X/bg2175Isup2.hkl
A mixture of manganese chloride(1 mmol), 4-methylbenzoic acid (1 mmol), 2,2'-bipyridyl(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
SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. The structure of (I), showing the atomic numbering scheme. Non-H atoms are shown as 30% probability displacement ellipsoids. |
[Mn(C8H7O2)4(C10H8N2)] | F(000) = 1572 |
Mr = 753.68 | Dx = 1.317 Mg m−3 |
Orthorhombic, Pccn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ab 2ac | Cell parameters from 3500 reflections |
a = 13.6159 (2) Å | θ = 1.4–28.0° |
b = 14.2585 (2) Å | µ = 0.40 mm−1 |
c = 19.5732 (3) Å | T = 273 K |
V = 3799.99 (10) Å3 | Block, colourless |
Z = 4 | 0.20 × 0.16 × 0.11 mm |
Bruker APEXII area-detector diffractometer | 4378 independent reflections |
Radiation source: fine-focus sealed tube | 2297 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.071 |
ϕ and ω scans | θmax = 27.5°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −17→17 |
Tmin = 0.93, Tmax = 0.96 | k = −18→18 |
30915 measured reflections | l = −25→25 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.131 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0559P)2 + 0.3551P] where P = (Fo2 + 2Fc2)/3 |
4378 reflections | (Δ/σ)max = 0.002 |
243 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
[Mn(C8H7O2)4(C10H8N2)] | V = 3799.99 (10) Å3 |
Mr = 753.68 | Z = 4 |
Orthorhombic, Pccn | Mo Kα radiation |
a = 13.6159 (2) Å | µ = 0.40 mm−1 |
b = 14.2585 (2) Å | T = 273 K |
c = 19.5732 (3) Å | 0.20 × 0.16 × 0.11 mm |
Bruker APEXII area-detector diffractometer | 4378 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2297 reflections with I > 2σ(I) |
Tmin = 0.93, Tmax = 0.96 | Rint = 0.071 |
30915 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.131 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.22 e Å−3 |
4378 reflections | Δρmin = −0.24 e Å−3 |
243 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | 0.8584 (2) | 0.14977 (18) | 0.04194 (12) | 0.0562 (7) | |
C2 | 0.95641 (18) | 0.13966 (17) | 0.00816 (12) | 0.0540 (6) | |
C3 | 1.0397 (2) | 0.17677 (19) | 0.03729 (13) | 0.0653 (7) | |
H3 | 1.0347 | 0.2093 | 0.0783 | 0.078* | |
C4 | 1.1305 (2) | 0.1667 (2) | 0.00678 (15) | 0.0748 (8) | |
H4 | 1.1858 | 0.1922 | 0.0276 | 0.090* | |
C5 | 1.1402 (2) | 0.1191 (2) | −0.05468 (15) | 0.0687 (8) | |
C6 | 1.0571 (2) | 0.0818 (2) | −0.08347 (14) | 0.0721 (8) | |
H6 | 1.0621 | 0.0485 | −0.1242 | 0.087* | |
C7 | 0.9662 (2) | 0.09274 (19) | −0.05331 (13) | 0.0662 (7) | |
H7 | 0.9108 | 0.0682 | −0.0746 | 0.079* | |
C8 | 1.2399 (2) | 0.1071 (3) | −0.08752 (16) | 0.0941 (11) | |
H8A | 1.2416 | 0.0489 | −0.1122 | 0.141* | |
H8B | 1.2896 | 0.1066 | −0.0528 | 0.141* | |
H8C | 1.2517 | 0.1581 | −0.1185 | 0.141* | |
C9 | 0.9071 (2) | 0.39242 (17) | 0.11458 (13) | 0.0563 (7) | |
C10 | 1.01048 (19) | 0.40889 (18) | 0.13322 (12) | 0.0532 (6) | |
C11 | 1.0399 (2) | 0.3921 (2) | 0.19970 (13) | 0.0752 (8) | |
H11 | 0.9946 | 0.3709 | 0.2317 | 0.090* | |
C12 | 1.1359 (2) | 0.4068 (3) | 0.21850 (15) | 0.0940 (11) | |
H12 | 1.1546 | 0.3943 | 0.2633 | 0.113* | |
C13 | 1.2057 (2) | 0.4397 (3) | 0.17272 (15) | 0.0834 (9) | |
C14 | 1.1752 (2) | 0.4553 (2) | 0.10613 (14) | 0.0757 (8) | |
H14 | 1.2203 | 0.4767 | 0.0740 | 0.091* | |
C15 | 1.07983 (19) | 0.4399 (2) | 0.08677 (13) | 0.0645 (7) | |
H15 | 1.0614 | 0.4504 | 0.0417 | 0.077* | |
C16 | 1.3096 (2) | 0.4584 (4) | 0.19472 (18) | 0.1358 (17) | |
H16A | 1.3107 | 0.4735 | 0.2425 | 0.204* | |
H16B | 1.3356 | 0.5101 | 0.1690 | 0.204* | |
H16C | 1.3489 | 0.4036 | 0.1867 | 0.204* | |
C17 | 0.9252 (2) | 0.1655 (2) | 0.25483 (13) | 0.0669 (8) | |
H17 | 0.9504 | 0.1479 | 0.2126 | 0.080* | |
C18 | 0.9816 (2) | 0.1503 (2) | 0.31183 (14) | 0.0731 (8) | |
H18 | 1.0436 | 0.1235 | 0.3081 | 0.088* | |
C19 | 0.9451 (2) | 0.1753 (2) | 0.37414 (14) | 0.0765 (9) | |
H19 | 0.9820 | 0.1665 | 0.4136 | 0.092* | |
C20 | 0.8529 (2) | 0.2136 (2) | 0.37739 (13) | 0.0683 (8) | |
H20 | 0.8262 | 0.2297 | 0.4195 | 0.082* | |
C21 | 0.79986 (17) | 0.22837 (15) | 0.31865 (11) | 0.0482 (6) | |
Mn1 | 0.7500 | 0.2500 | 0.16384 (2) | 0.05147 (19) | |
N1 | 0.83575 (14) | 0.20438 (14) | 0.25699 (9) | 0.0528 (5) | |
O2 | 0.78417 (13) | 0.12153 (14) | 0.00966 (9) | 0.0733 (6) | |
O3 | 0.84470 (13) | 0.37396 (13) | 0.15885 (8) | 0.0639 (5) | |
O4 | 0.88686 (13) | 0.39944 (15) | 0.04991 (9) | 0.0709 (5) | |
H4A | 0.8276 | 0.3932 | 0.0442 | 0.106* | |
O5 | 0.85649 (12) | 0.18654 (14) | 0.10029 (8) | 0.0678 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0513 (17) | 0.0700 (18) | 0.0472 (14) | −0.0002 (14) | 0.0052 (13) | 0.0032 (12) |
C2 | 0.0490 (16) | 0.0645 (16) | 0.0486 (13) | −0.0017 (13) | 0.0049 (13) | −0.0004 (12) |
C3 | 0.0604 (19) | 0.0755 (19) | 0.0600 (16) | −0.0043 (15) | 0.0059 (14) | −0.0106 (13) |
C4 | 0.0501 (18) | 0.096 (2) | 0.078 (2) | −0.0066 (16) | 0.0084 (15) | −0.0094 (17) |
C5 | 0.0552 (19) | 0.085 (2) | 0.0658 (17) | 0.0056 (16) | 0.0149 (15) | 0.0032 (15) |
C6 | 0.070 (2) | 0.087 (2) | 0.0592 (16) | 0.0016 (17) | 0.0170 (16) | −0.0097 (14) |
C7 | 0.0585 (19) | 0.085 (2) | 0.0555 (15) | −0.0070 (15) | 0.0102 (14) | −0.0086 (14) |
C8 | 0.064 (2) | 0.125 (3) | 0.093 (2) | 0.0086 (19) | 0.0257 (18) | 0.0028 (19) |
C9 | 0.0590 (18) | 0.0595 (16) | 0.0503 (15) | −0.0025 (14) | −0.0041 (14) | 0.0003 (12) |
C10 | 0.0432 (16) | 0.0671 (17) | 0.0493 (14) | −0.0028 (13) | −0.0035 (12) | 0.0007 (12) |
C11 | 0.061 (2) | 0.109 (2) | 0.0553 (17) | −0.0080 (17) | −0.0025 (15) | 0.0113 (15) |
C12 | 0.069 (2) | 0.158 (3) | 0.0550 (17) | −0.010 (2) | −0.0133 (17) | 0.0166 (19) |
C13 | 0.0523 (19) | 0.131 (3) | 0.0671 (19) | −0.0014 (19) | −0.0081 (16) | 0.0071 (17) |
C14 | 0.0509 (18) | 0.115 (2) | 0.0611 (17) | −0.0078 (17) | 0.0002 (15) | 0.0089 (15) |
C15 | 0.0491 (17) | 0.089 (2) | 0.0557 (15) | −0.0053 (15) | −0.0029 (14) | 0.0112 (13) |
C16 | 0.053 (2) | 0.262 (5) | 0.093 (3) | −0.020 (3) | −0.016 (2) | 0.023 (3) |
C17 | 0.0578 (18) | 0.087 (2) | 0.0556 (16) | 0.0139 (16) | 0.0053 (14) | −0.0018 (13) |
C18 | 0.0575 (18) | 0.093 (2) | 0.0689 (18) | 0.0218 (16) | −0.0041 (16) | 0.0050 (15) |
C19 | 0.066 (2) | 0.106 (2) | 0.0577 (17) | 0.0165 (18) | −0.0163 (15) | 0.0040 (15) |
C20 | 0.068 (2) | 0.091 (2) | 0.0464 (15) | 0.0106 (17) | −0.0047 (14) | −0.0017 (13) |
C21 | 0.0472 (15) | 0.0535 (15) | 0.0438 (12) | −0.0031 (11) | −0.0006 (11) | −0.0001 (10) |
Mn1 | 0.0442 (3) | 0.0715 (4) | 0.0387 (3) | −0.0011 (3) | 0.000 | 0.000 |
N1 | 0.0456 (13) | 0.0664 (13) | 0.0463 (11) | 0.0021 (11) | 0.0025 (10) | 0.0006 (9) |
O2 | 0.0498 (12) | 0.1187 (16) | 0.0513 (10) | −0.0112 (11) | 0.0035 (9) | −0.0116 (10) |
O3 | 0.0559 (12) | 0.0845 (13) | 0.0513 (10) | −0.0149 (10) | 0.0057 (9) | −0.0031 (9) |
O4 | 0.0500 (12) | 0.1085 (15) | 0.0542 (11) | −0.0087 (11) | −0.0051 (9) | 0.0123 (10) |
O5 | 0.0533 (11) | 0.0962 (14) | 0.0540 (11) | 0.0019 (10) | 0.0080 (9) | −0.0174 (9) |
C1—O5 | 1.257 (3) | C13—C14 | 1.386 (4) |
C1—O2 | 1.258 (3) | C13—C16 | 1.503 (4) |
C1—C2 | 1.496 (3) | C14—C15 | 1.371 (3) |
C2—C3 | 1.375 (3) | C14—H14 | 0.9300 |
C2—C7 | 1.383 (3) | C15—H15 | 0.9300 |
C3—C4 | 1.381 (3) | C16—H16A | 0.9600 |
C3—H3 | 0.9300 | C16—H16B | 0.9600 |
C4—C5 | 1.388 (4) | C16—H16C | 0.9600 |
C4—H4 | 0.9300 | C17—N1 | 1.339 (3) |
C5—C6 | 1.371 (4) | C17—C18 | 1.372 (3) |
C5—C8 | 1.512 (4) | C17—H17 | 0.9300 |
C6—C7 | 1.380 (3) | C18—C19 | 1.364 (4) |
C6—H6 | 0.9300 | C18—H18 | 0.9300 |
C7—H7 | 0.9300 | C19—C20 | 1.370 (3) |
C8—H8A | 0.9600 | C19—H19 | 0.9300 |
C8—H8B | 0.9600 | C20—C21 | 1.374 (3) |
C8—H8C | 0.9600 | C20—H20 | 0.9300 |
C9—O3 | 1.242 (3) | C21—N1 | 1.346 (3) |
C9—O4 | 1.300 (3) | C21—C21i | 1.491 (5) |
C9—C10 | 1.472 (3) | Mn1—O5i | 2.1139 (16) |
C10—C11 | 1.382 (3) | Mn1—O5 | 2.1139 (16) |
C10—C15 | 1.383 (3) | Mn1—O3i | 2.1900 (18) |
C11—C12 | 1.374 (4) | Mn1—O3 | 2.1900 (18) |
C11—H11 | 0.9300 | Mn1—N1 | 2.2607 (19) |
C12—C13 | 1.388 (4) | Mn1—N1i | 2.2607 (19) |
C12—H12 | 0.9300 | O4—H4A | 0.8200 |
O5—C1—O2 | 125.0 (2) | C14—C15—C10 | 121.1 (2) |
O5—C1—C2 | 117.4 (2) | C14—C15—H15 | 119.4 |
O2—C1—C2 | 117.6 (2) | C10—C15—H15 | 119.4 |
C3—C2—C7 | 117.9 (2) | C13—C16—H16A | 109.5 |
C3—C2—C1 | 121.0 (2) | C13—C16—H16B | 109.5 |
C7—C2—C1 | 121.1 (2) | H16A—C16—H16B | 109.5 |
C2—C3—C4 | 121.3 (2) | C13—C16—H16C | 109.5 |
C2—C3—H3 | 119.4 | H16A—C16—H16C | 109.5 |
C4—C3—H3 | 119.4 | H16B—C16—H16C | 109.5 |
C3—C4—C5 | 120.7 (3) | N1—C17—C18 | 123.3 (2) |
C3—C4—H4 | 119.6 | N1—C17—H17 | 118.4 |
C5—C4—H4 | 119.6 | C18—C17—H17 | 118.4 |
C6—C5—C4 | 117.9 (3) | C19—C18—C17 | 118.8 (3) |
C6—C5—C8 | 121.5 (3) | C19—C18—H18 | 120.6 |
C4—C5—C8 | 120.6 (3) | C17—C18—H18 | 120.6 |
C5—C6—C7 | 121.4 (3) | C18—C19—C20 | 118.6 (2) |
C5—C6—H6 | 119.3 | C18—C19—H19 | 120.7 |
C7—C6—H6 | 119.3 | C20—C19—H19 | 120.7 |
C6—C7—C2 | 120.9 (3) | C19—C20—C21 | 120.3 (2) |
C6—C7—H7 | 119.6 | C19—C20—H20 | 119.9 |
C2—C7—H7 | 119.6 | C21—C20—H20 | 119.9 |
C5—C8—H8A | 109.5 | N1—C21—C20 | 121.3 (2) |
C5—C8—H8B | 109.5 | N1—C21—C21i | 115.82 (13) |
H8A—C8—H8B | 109.5 | C20—C21—C21i | 122.83 (16) |
C5—C8—H8C | 109.5 | O5i—Mn1—O5 | 107.91 (10) |
H8A—C8—H8C | 109.5 | O5i—Mn1—O3i | 85.14 (7) |
H8B—C8—H8C | 109.5 | O5—Mn1—O3i | 91.85 (7) |
O3—C9—O4 | 123.4 (2) | O5i—Mn1—O3 | 91.85 (7) |
O3—C9—C10 | 121.0 (2) | O5—Mn1—O3 | 85.14 (7) |
O4—C9—C10 | 115.6 (2) | O3i—Mn1—O3 | 174.89 (9) |
C11—C10—C15 | 118.4 (2) | O5i—Mn1—N1 | 162.18 (7) |
C11—C10—C9 | 118.8 (2) | O5—Mn1—N1 | 89.84 (7) |
C15—C10—C9 | 122.7 (2) | O3i—Mn1—N1 | 96.19 (7) |
C12—C11—C10 | 120.1 (3) | O3—Mn1—N1 | 87.94 (7) |
C12—C11—H11 | 120.0 | O5i—Mn1—N1i | 89.84 (7) |
C10—C11—H11 | 120.0 | O5—Mn1—N1i | 162.18 (7) |
C11—C12—C13 | 122.0 (3) | O3i—Mn1—N1i | 87.94 (7) |
C11—C12—H12 | 119.0 | O3—Mn1—N1i | 96.19 (7) |
C13—C12—H12 | 119.0 | N1—Mn1—N1i | 72.48 (10) |
C14—C13—C12 | 117.1 (3) | C17—N1—C21 | 117.6 (2) |
C14—C13—C16 | 121.5 (3) | C17—N1—Mn1 | 124.29 (15) |
C12—C13—C16 | 121.3 (3) | C21—N1—Mn1 | 117.55 (15) |
C15—C14—C13 | 121.2 (3) | C9—O3—Mn1 | 127.24 (16) |
C15—C14—H14 | 119.4 | C9—O4—H4A | 109.5 |
C13—C14—H14 | 119.4 | C1—O5—Mn1 | 136.66 (17) |
Symmetry code: (i) −x+3/2, −y+1/2, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4A···O2i | 0.82 | 1.68 | 2.477 (2) | 164 |
Symmetry code: (i) −x+3/2, −y+1/2, z. |
Experimental details
Crystal data | |
Chemical formula | [Mn(C8H7O2)4(C10H8N2)] |
Mr | 753.68 |
Crystal system, space group | Orthorhombic, Pccn |
Temperature (K) | 273 |
a, b, c (Å) | 13.6159 (2), 14.2585 (2), 19.5732 (3) |
V (Å3) | 3799.99 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.40 |
Crystal size (mm) | 0.20 × 0.16 × 0.11 |
Data collection | |
Diffractometer | Bruker APEXII area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.93, 0.96 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 30915, 4378, 2297 |
Rint | 0.071 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.131, 1.01 |
No. of reflections | 4378 |
No. of parameters | 243 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.24 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4A···O2i | 0.82 | 1.68 | 2.477 (2) | 164.0 |
Symmetry code: (i) −x+3/2, −y+1/2, z. |
Acknowledgements
The authors thank Guang Dong Ocean University for supporting this study.
References
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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-methylbenzate 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 Mn complex obtained by the reaction of 4-methylbenzoic acid, 2,2'-bipyridyl and manganese chloride in alkaline aqueous solution.
As illustrated in Figure 1, the MnII atom lies on a centre of symmetry, and is surrounded by distorted octahedral environment defined by four carboxyl O atoms from four monodentate 4-methylbenzate ligands and two N atoms from one 2,2'-bipyridyl ligand. The packing is governed by a O—H···O hydrogen bond (Table 1) and a weak π-π stacking interaction between the parallel pyridyl ring of a 2,2'-bipyridyl and a phenyl ring of 4-methylbenzoic group of neighboring complexes (1.5-x, 0.5-y, z), with a centroid to centroid distance of 3.839 (2) Å.