Bis(1H-imidazole-κN³)bis­(4-methyl­benzoato-κO)zinc(II) 4-methyl­benzoic acid disolvate

The mol­ecular structure of the title compound, [Zn(C₈H₇O₂)₂(C₇H₆N₂)₂]·2C₈H₈O₂, is composed of a mononuclear Zn^II complex, which possesses twofold rotation symmetry, and two uncoordinated 4-methyl­benzoic acid mol­ecules. The Zn^II atom displays a four-coordinate distorted tetra­hedral configuration, formed by two carboxylate O atoms of two monodentate 4-methyl­benzoate ligands and two N atoms of two benzimidazole mol­ecules. In the crystal structure, complex mol­ecules are linked by the 4-methyl­benzoic acid mol­ecules via N—H...O and O—H...O hydrogen bonds, giving rise to the formation of a supra­molecular structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.054
• wR factor = 0.120
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found





Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C21
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C17
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C20
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.

Bis(1H-imidazole-κN³)bis(4-methylbenzoato-κO)zinc(II) 4-methylbenzoic acid disolvate

Crystal data

[Zn(C8H7O2)2(C7H6N2)2]·2C8H8O2	F(000) = 1760
Mr = 844.21	Dx = 1.345 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 12833 reflections
a = 27.8162 (15) Å	θ = 2.4–25.0°
b = 6.0773 (3) Å	µ = 0.65 mm^−1
c = 24.8610 (13) Å	T = 293 K
β = 97.141 (3)°	Prism, colorless
V = 4170.1 (4) Å^3	0.32 × 0.24 × 0.18 mm
Z = 4

Data collection

Bruker P4 diffractometer	3660 independent reflections
Radiation source: fine-focus sealed tube	1941 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.099
Detector resolution: 10 pixels mm^-1	θmax = 25.0°, θmin = 2.4°
ω scans	h = −32→32
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −7→5
Tmin = 0.820, Tmax = 0.892	l = −29→23
12833 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0344P)^2] where P = (Fo^2 + 2Fc^2)/3
3660 reflections	(Δ/σ)max < 0.001
272 parameters	Δρmax = 0.29 e Å^−3
1 restraint	Δρmin = −0.34 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Zn1	0.5000	0.48042 (10)	0.2500	0.0452 (2)
N1	0.55698 (11)	0.6868 (5)	0.26085 (13)	0.0442 (9)
N2	0.59675 (12)	0.9859 (5)	0.29192 (14)	0.0589 (9)
O1	0.49076 (10)	0.5198 (5)	0.13250 (13)	0.0750 (9)
O2	0.51578 (9)	0.2706 (4)	0.19495 (12)	0.0521 (8)
O3	0.62655 (13)	0.3374 (5)	0.35730 (14)	0.0932 (12)
O4	0.59956 (12)	0.6384 (5)	0.39456 (14)	0.0735 (9)
C1	0.51123 (14)	0.3440 (7)	0.14659 (19)	0.0479 (11)
C2	0.53359 (13)	0.2096 (6)	0.10566 (16)	0.0411 (10)
C3	0.55567 (13)	0.0098 (6)	0.11928 (17)	0.0542 (11)
C4	0.57507 (15)	−0.1134 (7)	0.0805 (2)	0.0624 (13)
C5	0.57405 (15)	−0.0411 (7)	0.02788 (19)	0.0597 (12)
C6	0.55232 (16)	0.1598 (8)	0.01444 (18)	0.0637 (13)
C7	0.53277 (14)	0.2831 (7)	0.05298 (18)	0.0555 (12)
C8	0.59474 (17)	−0.1747 (8)	−0.0147 (2)	0.0890 (17)
C9	0.55551 (15)	0.8734 (7)	0.28793 (18)	0.0558 (12)
C10	0.62870 (16)	0.8649 (7)	0.26616 (17)	0.0517 (11)
C11	0.67676 (18)	0.9028 (9)	0.2594 (2)	0.0816 (16)
C12	0.69842 (18)	0.7436 (11)	0.2315 (2)	0.0939 (18)
C13	0.67458 (17)	0.5535 (9)	0.2124 (2)	0.0811 (16)
C14	0.62677 (14)	0.5152 (7)	0.21958 (18)	0.0604 (12)
C15	0.60393 (14)	0.6767 (6)	0.24666 (16)	0.0451 (10)
C16	0.63399 (19)	0.5135 (8)	0.38003 (18)	0.0644 (13)
C17	0.68325 (19)	0.6078 (7)	0.39365 (18)	0.0602 (12)
C18	0.69000 (19)	0.8104 (8)	0.4178 (2)	0.0850 (16)
C19	0.7363 (2)	0.8940 (9)	0.4308 (2)	0.0975 (18)
C20	0.7765 (2)	0.7780 (11)	0.4198 (2)	0.0910 (17)
C21	0.7690 (2)	0.5823 (12)	0.3949 (3)	0.109 (2)
C22	0.7230 (2)	0.4951 (9)	0.3822 (2)	0.0936 (17)
C23	0.8271 (2)	0.8726 (10)	0.4346 (3)	0.133 (2)
H2	0.6024	1.1109	0.3077	0.071*
H3	0.5575	−0.0419	0.1547	0.065*
H4	0.5892	−0.2487	0.0902	0.075*
H6	0.5509	0.2121	−0.0209	0.076*
H7	0.5187	0.4185	0.0433	0.067*
H8A	0.6294	−0.1769	−0.0071	0.134*
H8B	0.5855	−0.1101	−0.0497	0.134*
H8C	0.5825	−0.3224	−0.0144	0.134*
H9	0.5282	0.9213	0.3028	0.067*
H10	0.5706 (7)	0.602 (7)	0.3839 (19)	0.088*
H11	0.6933	1.0281	0.2728	0.098*
H12	0.7304	0.7641	0.2252	0.113*
H13	0.6911	0.4494	0.1944	0.097*
H14	0.6107	0.3875	0.2069	0.073*
H18	0.6634	0.8919	0.4255	0.102*
H19	0.7403	1.0311	0.4474	0.117*
H21	0.7955	0.5031	0.3860	0.131*
H22	0.7193	0.3578	0.3657	0.112*
H23A	0.8376	0.8466	0.4723	0.200*
H23B	0.8266	1.0280	0.4277	0.200*
H23C	0.8492	0.8027	0.4132	0.200*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0474 (4)	0.0380 (4)	0.0520 (5)	0.000	0.0128 (3)	0.000
N1	0.043 (2)	0.0373 (19)	0.055 (2)	−0.0003 (16)	0.0154 (18)	−0.0047 (16)
N2	0.064 (2)	0.0375 (19)	0.074 (3)	−0.008 (2)	0.006 (2)	−0.0054 (19)
O1	0.079 (2)	0.0565 (19)	0.095 (3)	0.0297 (18)	0.0329 (18)	0.0127 (17)
O2	0.067 (2)	0.0433 (16)	0.049 (2)	−0.0005 (14)	0.0174 (16)	0.0000 (14)
O3	0.141 (3)	0.054 (2)	0.084 (3)	−0.022 (2)	0.009 (2)	−0.0188 (18)
O4	0.076 (2)	0.070 (2)	0.072 (3)	−0.013 (2)	0.001 (2)	−0.0094 (18)
C1	0.045 (3)	0.042 (3)	0.059 (3)	−0.002 (2)	0.015 (2)	−0.001 (2)
C2	0.042 (2)	0.037 (2)	0.045 (3)	−0.0002 (19)	0.011 (2)	0.0021 (19)
C3	0.066 (3)	0.047 (2)	0.052 (3)	0.006 (2)	0.016 (2)	0.005 (2)
C4	0.074 (3)	0.049 (3)	0.067 (4)	0.011 (2)	0.021 (3)	0.001 (2)
C5	0.066 (3)	0.056 (3)	0.061 (3)	−0.007 (2)	0.027 (3)	−0.012 (2)
C6	0.077 (3)	0.070 (3)	0.046 (3)	0.000 (3)	0.017 (3)	−0.001 (2)
C7	0.059 (3)	0.050 (3)	0.058 (3)	0.004 (2)	0.011 (3)	0.009 (2)
C8	0.105 (4)	0.088 (4)	0.082 (4)	0.003 (3)	0.041 (3)	−0.024 (3)
C9	0.052 (3)	0.043 (3)	0.073 (3)	−0.002 (2)	0.011 (2)	−0.003 (2)
C10	0.047 (3)	0.052 (3)	0.056 (3)	−0.003 (2)	0.003 (2)	0.009 (2)
C11	0.061 (4)	0.077 (4)	0.106 (5)	−0.019 (3)	0.007 (3)	0.009 (3)
C12	0.046 (3)	0.128 (5)	0.109 (5)	−0.017 (4)	0.015 (3)	0.013 (4)
C13	0.050 (3)	0.107 (4)	0.090 (4)	0.016 (3)	0.020 (3)	−0.011 (3)
C14	0.053 (3)	0.060 (3)	0.070 (3)	0.010 (3)	0.011 (2)	−0.005 (2)
C15	0.044 (3)	0.047 (3)	0.044 (3)	0.004 (2)	0.006 (2)	0.007 (2)
C16	0.096 (4)	0.046 (3)	0.051 (3)	−0.007 (3)	0.006 (3)	0.010 (3)
C17	0.077 (4)	0.049 (3)	0.055 (3)	0.000 (3)	0.007 (3)	0.000 (2)
C18	0.074 (4)	0.067 (4)	0.113 (5)	−0.005 (3)	0.007 (3)	−0.024 (3)
C19	0.088 (4)	0.072 (4)	0.129 (6)	−0.006 (4)	0.000 (4)	−0.019 (3)
C20	0.084 (5)	0.092 (5)	0.095 (5)	0.001 (4)	0.002 (4)	0.014 (4)
C21	0.098 (5)	0.106 (6)	0.123 (6)	0.033 (4)	0.015 (4)	−0.002 (4)
C22	0.102 (4)	0.069 (4)	0.110 (5)	0.010 (4)	0.016 (4)	−0.018 (3)
C23	0.081 (4)	0.169 (6)	0.143 (7)	−0.017 (4)	−0.017 (4)	0.025 (5)

Geometric parameters (Å, º)

Zn1—N1	2.013 (3)	C8—H8C	0.9600
Zn1—O2	1.960 (3)	C9—H9	0.9300
O1—C1	1.240 (4)	C10—C11	1.387 (6)
O2—C1	1.274 (4)	C10—C15	1.391 (5)
O3—C16	1.216 (5)	C11—C12	1.372 (7)
O4—C16	1.308 (5)	C11—H11	0.9300
Zn1—N1^i	2.013 (3)	C12—C13	1.386 (7)
Zn1—O2^i	1.960 (3)	C12—H12	0.9300
N1—C9	1.322 (4)	C13—C14	1.383 (5)
N1—C15	1.396 (4)	C13—H13	0.9300
N2—C9	1.329 (4)	C14—C15	1.388 (5)
N2—C10	1.372 (5)	C14—H14	0.9300
N2—H2	0.8600	C16—C17	1.485 (6)
O4—H10	0.85 (3)	C17—C22	1.361 (6)
C1—C2	1.499 (5)	C17—C18	1.373 (6)
C2—C7	1.381 (5)	C18—C19	1.385 (6)
C2—C3	1.384 (5)	C18—H18	0.9300
C3—C4	1.382 (5)	C19—C20	1.378 (7)
C3—H3	0.9300	C19—H19	0.9300
C4—C5	1.377 (6)	C20—C21	1.345 (7)
C4—H4	0.9300	C20—C23	1.523 (7)
C5—C6	1.385 (6)	C21—C22	1.384 (7)
C5—C8	1.504 (5)	C21—H21	0.9300
C6—C7	1.380 (5)	C22—H22	0.9300
C6—H6	0.9300	C23—H23A	0.9600
C7—H7	0.9300	C23—H23B	0.9600
C8—H8A	0.9600	C23—H23C	0.9600
C8—H8B	0.9600
N1—Zn1—N1^i	102.91 (17)	C10—C15—N1	108.3 (4)
O2—Zn1—N1	104.96 (12)	C11—C10—C15	122.5 (5)
O2^i—Zn1—N1	123.56 (12)	C11—C12—C13	122.6 (5)
O2^i—Zn1—O2	98.81 (16)	C11—C12—H12	118.7
N1—C9—N2	113.5 (4)	C12—C11—C10	115.8 (5)
N1—C9—H9	123.3	C12—C11—H11	122.1
N2—C9—H9	123.3	C12—C13—H13	119.2
N2—C10—C11	131.1 (5)	C13—C12—H12	118.7
N2—C10—C15	106.4 (4)	C13—C14—C15	116.6 (4)
O1—C1—O2	123.8 (4)	C13—C14—H14	121.7
O1—C1—C2	119.5 (4)	C14—C13—C12	121.5 (5)
O2^i—Zn1—N1^i	104.96 (12)	C14—C13—H13	119.2
O2—Zn1—N1^i	123.56 (12)	C14—C15—C10	120.9 (4)
O2—C1—C2	116.7 (4)	C14—C15—N1	130.7 (4)
O3—C16—O4	123.4 (5)	C15—N1—Zn1	133.2 (3)
O3—C16—C17	123.0 (5)	C15—C14—H14	121.7
O4—C16—C17	113.6 (4)	C16—O4—H10	118 (3)
C1—O2—Zn1	115.2 (2)	C17—C18—C19	120.3 (5)
C2—C3—H3	119.8	C17—C18—H18	119.9
C2—C7—H7	119.3	C17—C22—C21	120.8 (5)
C3—C2—C1	121.4 (4)	C17—C22—H22	119.6
C3—C4—H4	119.1	C18—C17—C16	121.2 (5)
C4—C3—C2	120.3 (4)	C18—C19—H19	119.3
C4—C3—H3	119.8	C19—C18—H18	119.9
C4—C5—C6	117.9 (4)	C19—C20—C23	120.5 (6)
C4—C5—C8	122.1 (4)	C20—C19—C18	121.3 (5)
C5—C4—C3	121.7 (4)	C20—C19—H19	119.3
C5—C4—H4	119.1	C20—C21—C22	122.0 (6)
C5—C6—H6	119.7	C20—C21—H21	119.0
C5—C8—H8A	109.5	C20—C23—H23A	109.5
C5—C8—H8B	109.5	C20—C23—H23B	109.5
C5—C8—H8C	109.5	C20—C23—H23C	109.5
C6—C5—C8	120.0 (4)	C21—C20—C19	117.4 (6)
C6—C7—C2	121.4 (4)	C21—C20—C23	122.1 (7)
C6—C7—H7	119.3	C21—C22—H22	119.6
C7—C2—C1	120.6 (4)	C22—C17—C18	118.2 (5)
C7—C2—C3	118.0 (4)	C22—C17—C16	120.6 (5)
C7—C6—C5	120.6 (4)	C22—C21—H21	119.0
C7—C6—H6	119.7	H8A—C8—H8B	109.5
C9—N1—Zn1	121.9 (3)	H8A—C8—H8C	109.5
C9—N1—C15	104.8 (3)	H8B—C8—H8C	109.5
C9—N2—C10	107.0 (3)	H23A—C23—H23B	109.5
C9—N2—H2	126.5	H23A—C23—H23C	109.5
C10—N2—H2	126.5	H23B—C23—H23C	109.5
C10—C11—H11	122.1
Zn1—O2—C1—O1	−11.9 (5)	C3—C4—C5—C8	−179.5 (4)
Zn1—O2—C1—C2	166.2 (2)	C4—C5—C6—C7	0.5 (6)
Zn1—N1—C9—N2	178.7 (3)	C5—C6—C7—C2	−0.9 (6)
Zn1—N1—C15—C10	−178.1 (3)	C7—C2—C3—C4	−1.6 (6)
Zn1—N1—C15—C14	0.1 (6)	C8—C5—C6—C7	179.4 (4)
N1^i—Zn1—N1—C9	37.2 (3)	C9—N1—C15—C10	−0.6 (4)
N1^i—Zn1—N1—C15	−145.6 (4)	C9—N1—C15—C14	177.5 (4)
N1^i—Zn1—O2—C1	41.5 (3)	C9—N2—C10—C11	−178.3 (5)
N1—Zn1—O2—C1	−75.6 (3)	C9—N2—C10—C15	0.3 (4)
N2—C10—C11—C12	179.2 (5)	C10—N2—C9—N1	−0.8 (5)
N2—C10—C15—N1	0.2 (4)	C10—C11—C12—C13	−1.7 (8)
N2—C10—C15—C14	−178.2 (4)	C11—C12—C13—C14	1.2 (9)
O1—C1—C2—C3	−178.3 (4)	C11—C10—C15—N1	179.0 (4)
O1—C1—C2—C7	1.9 (6)	C11—C10—C15—C14	0.6 (6)
O2^i—Zn1—N1—C9	−80.7 (3)	C12—C13—C14—C15	0.2 (7)
O2—Zn1—N1—C9	167.7 (3)	C13—C14—C15—N1	−179.0 (4)
O2^i—Zn1—N1—C15	96.4 (4)	C13—C14—C15—C10	−1.1 (6)
O2—Zn1—N1—C15	−15.2 (4)	C15—N1—C9—N2	0.9 (5)
O2^i—Zn1—O2—C1	156.1 (3)	C15—C10—C11—C12	0.7 (7)
O2—C1—C2—C3	3.5 (6)	C16—C17—C18—C19	179.1 (5)
O2—C1—C2—C7	−176.4 (4)	C16—C17—C22—C21	−179.9 (5)
O3—C16—C17—C18	177.9 (5)	C17—C18—C19—C20	0.3 (9)
O3—C16—C17—C22	−1.8 (7)	C18—C17—C22—C21	0.3 (8)
O4—C16—C17—C18	−1.7 (6)	C18—C19—C20—C21	1.2 (9)
O4—C16—C17—C22	178.5 (4)	C18—C19—C20—C23	−179.8 (5)
C1—C2—C3—C4	178.5 (3)	C19—C20—C21—C22	−2.0 (10)
C1—C2—C7—C6	−178.7 (4)	C20—C21—C22—C17	1.3 (10)
C2—C3—C4—C5	1.3 (6)	C22—C17—C18—C19	−1.1 (8)
C3—C2—C7—C6	1.4 (6)	C23—C20—C21—C22	179.0 (5)
C3—C4—C5—C6	−0.7 (6)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3^ii	0.86	1.91	2.749 (5)	163
O4—H10···O1^i	0.85 (3)	1.78 (3)	2.620 (4)	175 (5)

Symmetry codes: (i) −x+1, y, −z+1/2; (ii) x, y+1, z.