Aqua­bis(1H-imidazole-κN³)bis­(4-methyl­benzoato-κ²O,O′)cobalt(II)

The Co^II centre in the title complex, [Co(C₈H₇O₂)₂(C₃H₄N₂)₂(H₂O)], has a distorted octa­hedral coordination geometry, involving three O atoms derived from two 4-methyl­benzoate ligands, two N atoms from the imidazole ligands and a water mol­ecule. Inter­molecular O—H...O and N—H...O hydrogen bonds along with π–π stacking inter­actions give rise to a layer structure.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.033
• wR factor = 0.081
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co1    -   O1      ..       9.88 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co1    -   O2      ..       9.74 su
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 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, 2004); 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, 2004); software used to prepare material for publication: SHELXL97.

Aquabis(1H-imidazole-κN³)bis(4-methylbenzoato-κ²O,O')cobalt(II)

Crystal data

[Co(C8H7O2)2(C3H4N2)2(H2O)]	F(000) = 1004
Mr = 483.38	Dx = 1.437 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 15987 reflections
a = 19.0095 (3) Å	θ = 1.3–25.1°
b = 5.8831 (1) Å	µ = 0.81 mm^−1
c = 20.4443 (3) Å	T = 273 K
β = 102.313 (1)°	Prism, pink
V = 2233.79 (6) Å^3	0.20 × 0.18 × 0.18 mm
Z = 4

Data collection

Bruker P4 diffractometer	3960 independent reflections
Radiation source: fine-focus sealed tube	3173 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 10 pixels mm^-1	θmax = 25.1°, θmin = 1.3°
ω scans	h = −19→22
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	k = −7→6
Tmin = 0.855, Tmax = 0.868	l = −20→24
16155 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.081	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0361P)^2 + 0.8956P] where P = (Fo^2 + 2Fc^2)/3
3960 reflections	(Δ/σ)max = 0.002
291 parameters	Δρmax = 0.39 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

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

	x	y	z	Uiso*/Ueq
Co1	0.628361 (15)	0.79173 (5)	0.863233 (14)	0.02762 (11)
O1	0.57683 (8)	0.4901 (3)	0.80864 (7)	0.0365 (4)
O2	0.58136 (8)	0.8105 (2)	0.75526 (7)	0.0345 (4)
O3	0.65282 (10)	0.3777 (3)	0.98836 (8)	0.0488 (4)
O4	0.67413 (9)	0.7327 (3)	0.96060 (8)	0.0445 (4)
O1W	0.66029 (8)	1.1367 (3)	0.87415 (7)	0.0371 (4)
N1	0.52958 (10)	0.8711 (3)	0.89003 (9)	0.0336 (4)
N2	0.43792 (11)	0.8377 (4)	0.93858 (10)	0.0456 (5)
N3	0.72942 (10)	0.7071 (3)	0.84098 (9)	0.0364 (5)
N4	0.82079 (11)	0.5512 (4)	0.80869 (11)	0.0487 (6)
C1	0.56094 (11)	0.6054 (4)	0.75540 (10)	0.0293 (5)
C2	0.51695 (11)	0.5021 (4)	0.69323 (10)	0.0302 (5)
C3	0.48726 (12)	0.2872 (4)	0.69432 (12)	0.0368 (6)
C4	0.44675 (13)	0.1931 (4)	0.63647 (12)	0.0422 (6)
C5	0.43471 (13)	0.3088 (4)	0.57631 (12)	0.0447 (6)
C6	0.46477 (14)	0.5231 (4)	0.57537 (12)	0.0461 (6)
C7	0.50520 (13)	0.6188 (4)	0.63272 (11)	0.0381 (6)
C8	0.38911 (17)	0.2040 (6)	0.51358 (14)	0.0708 (9)
C9	0.68141 (12)	0.5685 (4)	1.00077 (11)	0.0330 (5)
C10	0.72821 (11)	0.6123 (4)	1.06853 (10)	0.0310 (5)
C11	0.73856 (13)	0.4486 (4)	1.11858 (12)	0.0447 (6)
C12	0.78242 (14)	0.4924 (5)	1.18056 (12)	0.0520 (7)
C13	0.81753 (13)	0.6969 (5)	1.19456 (12)	0.0448 (6)
C14	0.80673 (14)	0.8594 (5)	1.14481 (12)	0.0484 (7)
C15	0.76279 (13)	0.8189 (4)	1.08322 (12)	0.0427 (6)
C16	0.86782 (16)	0.7405 (6)	1.26117 (13)	0.0702 (9)
C17	0.79282 (14)	0.7880 (5)	0.87880 (13)	0.0517 (7)
C18	0.84915 (14)	0.6935 (5)	0.85941 (14)	0.0519 (7)
C19	0.74909 (13)	0.5642 (4)	0.79928 (12)	0.0426 (6)
C20	0.49404 (13)	0.7331 (4)	0.92206 (12)	0.0428 (6)
C21	0.49351 (12)	1.0739 (4)	0.88599 (12)	0.0400 (6)
C22	0.43700 (13)	1.0541 (5)	0.91615 (13)	0.0475 (7)
H1W1	0.6353	1.2290	0.8467	0.056*
H1W2	0.6632	1.1888	0.9134	0.056*
H6N	0.8455	0.4693	0.7886	0.073*
H7N	0.4084	0.7781	0.9584	0.068*
H3	0.4946	0.2059	0.7342	0.044*
H4	0.4272	0.0488	0.6381	0.051*
H6	0.4575	0.6037	0.5354	0.055*
H7	0.5248	0.7628	0.6310	0.046*
H8A	0.4073	0.0556	0.5068	0.106*
H8B	0.3910	0.2984	0.4757	0.106*
H8C	0.3402	0.1915	0.5186	0.106*
H11	0.7158	0.3083	1.1104	0.054*
H12	0.7883	0.3809	1.2135	0.062*
H14	0.8297	0.9993	1.1531	0.058*
H15	0.7562	0.9324	1.0508	0.051*
H16A	0.9158	0.6967	1.2587	0.105*
H16B	0.8525	0.6533	1.2953	0.105*
H16C	0.8671	0.8993	1.2718	0.105*
H17	0.7962	0.8937	0.9132	0.062*
H18	0.8977	0.7203	0.8771	0.062*
H19	0.7172	0.4819	0.7671	0.051*
H20	0.5064	0.5821	0.9319	0.051*
H21	0.5059	1.2049	0.8656	0.048*
H22	0.4041	1.1669	0.9206	0.057*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.02915 (18)	0.02609 (18)	0.02877 (17)	0.00029 (13)	0.00877 (12)	−0.00032 (12)
O1	0.0432 (10)	0.0321 (9)	0.0328 (8)	0.0005 (7)	0.0049 (7)	0.0051 (7)
O2	0.0389 (9)	0.0276 (9)	0.0377 (9)	−0.0056 (7)	0.0099 (7)	−0.0002 (7)
O3	0.0614 (12)	0.0478 (11)	0.0403 (9)	−0.0194 (10)	0.0175 (8)	−0.0084 (8)
O4	0.0468 (11)	0.0510 (11)	0.0334 (9)	−0.0024 (8)	0.0034 (8)	0.0060 (8)
O1W	0.0448 (10)	0.0291 (9)	0.0384 (9)	0.0011 (7)	0.0112 (7)	0.0002 (7)
N1	0.0335 (11)	0.0367 (11)	0.0334 (10)	−0.0018 (9)	0.0134 (8)	−0.0009 (8)
N2	0.0364 (12)	0.0654 (16)	0.0392 (11)	−0.0109 (11)	0.0172 (9)	−0.0041 (11)
N3	0.0321 (11)	0.0372 (11)	0.0418 (11)	0.0015 (9)	0.0119 (9)	−0.0063 (9)
N4	0.0446 (14)	0.0470 (13)	0.0621 (14)	0.0130 (10)	0.0282 (11)	0.0012 (11)
C1	0.0266 (12)	0.0311 (13)	0.0322 (12)	0.0022 (10)	0.0105 (10)	0.0002 (10)
C2	0.0287 (12)	0.0294 (13)	0.0327 (12)	0.0030 (10)	0.0068 (10)	−0.0006 (10)
C3	0.0387 (14)	0.0326 (13)	0.0402 (13)	−0.0002 (11)	0.0111 (11)	0.0017 (11)
C4	0.0408 (15)	0.0354 (14)	0.0514 (15)	−0.0064 (11)	0.0121 (12)	−0.0060 (12)
C5	0.0385 (15)	0.0507 (17)	0.0447 (15)	0.0007 (12)	0.0081 (12)	−0.0099 (13)
C6	0.0554 (17)	0.0481 (16)	0.0331 (13)	0.0023 (13)	0.0057 (12)	0.0044 (12)
C7	0.0452 (15)	0.0319 (13)	0.0377 (13)	−0.0005 (11)	0.0095 (11)	0.0016 (11)
C8	0.070 (2)	0.081 (2)	0.0543 (18)	−0.0179 (18)	−0.0008 (16)	−0.0180 (16)
C9	0.0289 (13)	0.0421 (15)	0.0317 (12)	0.0014 (11)	0.0147 (10)	0.0002 (11)
C10	0.0287 (12)	0.0350 (13)	0.0308 (12)	0.0032 (10)	0.0096 (10)	0.0034 (10)
C11	0.0477 (16)	0.0391 (15)	0.0457 (15)	−0.0040 (12)	0.0061 (12)	0.0101 (12)
C12	0.0509 (17)	0.0624 (19)	0.0398 (15)	0.0049 (15)	0.0031 (13)	0.0205 (13)
C13	0.0325 (14)	0.0652 (19)	0.0370 (13)	0.0052 (13)	0.0082 (11)	−0.0001 (13)
C14	0.0479 (16)	0.0461 (16)	0.0474 (16)	−0.0094 (13)	0.0019 (13)	−0.0028 (12)
C15	0.0465 (15)	0.0396 (15)	0.0387 (13)	−0.0037 (12)	0.0018 (11)	0.0076 (11)
C16	0.0510 (19)	0.111 (3)	0.0425 (16)	0.0044 (18)	−0.0027 (14)	−0.0023 (16)
C17	0.0376 (16)	0.0638 (18)	0.0551 (16)	−0.0039 (13)	0.0131 (13)	−0.0203 (14)
C18	0.0309 (14)	0.0668 (19)	0.0590 (17)	−0.0010 (13)	0.0119 (13)	−0.0008 (15)
C19	0.0396 (15)	0.0388 (15)	0.0521 (15)	0.0023 (11)	0.0158 (12)	−0.0062 (12)
C20	0.0415 (15)	0.0451 (15)	0.0434 (14)	−0.0033 (12)	0.0121 (12)	0.0007 (12)
C21	0.0391 (14)	0.0367 (15)	0.0465 (14)	0.0010 (11)	0.0142 (12)	−0.0038 (11)
C22	0.0377 (15)	0.0542 (18)	0.0537 (16)	0.0050 (12)	0.0164 (13)	−0.0130 (13)

Geometric parameters (Å, º)

Co1—O1	2.2111 (15)	C5—C8	1.517 (4)
Co1—O2	2.2005 (15)	C6—C7	1.378 (3)
Co1—O4	2.0252 (16)	C6—H6	0.9300
Co1—O1W	2.1164 (15)	C7—H7	0.9300
Co1—N1	2.1174 (18)	C8—H8A	0.9600
Co1—N3	2.1257 (18)	C8—H8B	0.9600
O1—C1	1.263 (2)	C8—H8C	0.9600
O2—C1	1.268 (3)	C9—C10	1.500 (3)
O3—C9	1.249 (3)	C10—C15	1.384 (3)
O4—C9	1.257 (3)	C10—C11	1.389 (3)
O1W—H1W1	0.8501	C11—C12	1.384 (4)
O1W—H1W2	0.8499	C11—H11	0.9300
N1—C20	1.316 (3)	C12—C13	1.376 (4)
N1—C21	1.369 (3)	C12—H12	0.9300
N2—C20	1.336 (3)	C13—C14	1.379 (4)
N2—C22	1.352 (3)	C13—C16	1.510 (4)
N2—H7N	0.8350	C14—C15	1.375 (3)
N3—C19	1.307 (3)	C14—H14	0.9300
N3—C17	1.371 (3)	C15—H15	0.9300
N4—C19	1.337 (3)	C16—H16A	0.9600
N4—C18	1.352 (3)	C16—H16B	0.9600
N4—H6N	0.8398	C16—H16C	0.9600
C1—C2	1.494 (3)	C17—C18	1.339 (4)
C2—C3	1.387 (3)	C17—H17	0.9300
C2—C7	1.391 (3)	C18—H18	0.9300
C3—C4	1.382 (3)	C19—H19	0.9300
C3—H3	0.9300	C20—H20	0.9300
C4—C5	1.382 (4)	C21—C22	1.353 (3)
C4—H4	0.9300	C21—H21	0.9300
C5—C6	1.386 (4)	C22—H22	0.9300
O2—Co1—O1	59.50 (5)	C6—C7—H7	119.7
O4—Co1—O1	114.19 (6)	C7—C2—C1	120.7 (2)
O4—Co1—O2	172.78 (6)	C7—C6—C5	121.1 (2)
O4—Co1—O1W	90.41 (6)	C7—C6—H6	119.5
O4—Co1—N1	90.13 (7)	C9—O4—Co1	137.60 (16)
O4—Co1—N3	87.24 (7)	C10—C11—H11	119.7
O1W—Co1—O1	155.39 (6)	C10—C15—H15	119.4
O1W—Co1—O2	95.95 (6)	C11—C10—C9	121.6 (2)
O1W—Co1—N1	90.65 (7)	C11—C12—H12	119.2
O1W—Co1—N3	89.73 (7)	C12—C11—C10	120.6 (2)
N1—Co1—O1	89.18 (7)	C12—C11—H11	119.7
N1—Co1—O2	93.19 (6)	C12—C13—C14	117.6 (2)
N1—Co1—N3	177.35 (7)	C12—C13—C16	121.5 (3)
N3—Co1—O1	91.56 (7)	C13—C12—C11	121.6 (2)
N3—Co1—O2	89.38 (7)	C13—C12—H12	119.2
Co1—O1W—H1W1	115.8	C13—C14—H14	119.3
Co1—O1W—H1W2	113.9	C13—C16—H16A	109.5
O1—C1—O2	119.7 (2)	C13—C16—H16B	109.5
O1—C1—C2	120.1 (2)	C13—C16—H16C	109.5
O2—C1—C2	120.11 (19)	C14—C13—C16	120.9 (3)
O3—C9—O4	125.2 (2)	C14—C15—C10	121.2 (2)
O3—C9—C10	119.2 (2)	C14—C15—H15	119.4
O4—C9—C10	115.6 (2)	C15—C10—C11	117.6 (2)
N1—C20—N2	111.4 (2)	C15—C10—C9	120.8 (2)
N1—C20—H20	124.3	C15—C14—C13	121.4 (3)
N1—C21—H21	125.3	C15—C14—H14	119.3
N2—C20—H20	124.3	C17—N3—Co1	121.59 (15)
N2—C22—C21	106.3 (2)	C17—C18—N4	105.7 (2)
N2—C22—H22	126.8	C17—C18—H18	127.1
N3—C17—H17	124.7	C18—N4—H6N	123.9
N3—C19—N4	111.6 (2)	C18—C17—N3	110.6 (2)
N3—C19—H19	124.2	C18—C17—H17	124.7
N4—C18—H18	127.1	C19—N3—C17	104.6 (2)
N4—C19—H19	124.2	C19—N3—Co1	133.43 (17)
C1—O1—Co1	90.15 (13)	C19—N4—C18	107.6 (2)
C1—O2—Co1	90.52 (12)	C19—N4—H6N	128.5
C2—C3—H3	119.8	C20—N1—C21	105.28 (19)
C2—C7—H7	119.7	C20—N1—Co1	124.76 (17)
C3—C2—C1	120.9 (2)	C20—N2—C22	107.5 (2)
C3—C2—C7	118.4 (2)	C20—N2—H7N	125.7
C3—C4—H4	119.3	C21—N1—Co1	129.56 (15)
C4—C3—C2	120.4 (2)	C21—C22—H22	126.8
C4—C3—H3	119.8	C22—N2—H7N	126.7
C4—C5—C6	118.0 (2)	C22—C21—N1	109.5 (2)
C4—C5—C8	120.5 (3)	C22—C21—H21	125.3
C5—C4—C3	121.4 (2)	H1W1—O1W—H1W2	107.9
C5—C4—H4	119.3	H8A—C8—H8B	109.5
C5—C6—H6	119.5	H8A—C8—H8C	109.5
C5—C8—H8A	109.5	H8B—C8—H8C	109.5
C5—C8—H8B	109.5	H16A—C16—H16B	109.5
C5—C8—H8C	109.5	H16A—C16—H16C	109.5
C6—C5—C8	121.4 (3)	H16B—C16—H16C	109.5
C6—C7—C2	120.7 (2)
Co1—O1—C1—O2	3.05 (19)	O1W—Co1—N3—C17	46.4 (2)
Co1—O1—C1—C2	−175.66 (17)	O1W—Co1—N3—C19	−142.1 (2)
Co1—O2—C1—O1	−3.06 (19)	N1—Co1—O1—C1	92.42 (12)
Co1—O2—C1—C2	175.65 (17)	N1—Co1—O2—C1	−85.40 (12)
Co1—O4—C9—O3	−6.3 (4)	N1—Co1—O4—C9	88.2 (2)
Co1—O4—C9—C10	174.05 (15)	N1—C21—C22—N2	−0.4 (3)
Co1—N1—C20—N2	173.12 (15)	N3—Co1—O1—C1	−90.13 (13)
Co1—N1—C21—C22	−172.55 (16)	N3—Co1—O2—C1	93.94 (12)
Co1—N3—C17—C18	173.71 (18)	N3—Co1—O4—C9	−91.4 (2)
Co1—N3—C19—N4	−172.63 (16)	N3—C17—C18—N4	0.0 (3)
O1—Co1—O2—C1	1.76 (11)	C1—C2—C3—C4	−179.9 (2)
O1—Co1—O4—C9	−1.0 (2)	C1—C2—C7—C6	179.8 (2)
O1—Co1—N1—C20	56.37 (19)	C2—C3—C4—C5	0.0 (4)
O1—Co1—N1—C21	−131.96 (19)	C3—C2—C7—C6	0.3 (3)
O1—Co1—N3—C17	−158.21 (19)	C3—C4—C5—C6	0.3 (4)
O1—Co1—N3—C19	13.3 (2)	C3—C4—C5—C8	−179.1 (2)
O1—C1—C2—C3	6.1 (3)	C4—C5—C6—C7	−0.3 (4)
O1—C1—C2—C7	−173.5 (2)	C5—C6—C7—C2	0.0 (4)
O2—Co1—O1—C1	−1.77 (11)	C7—C2—C3—C4	−0.3 (3)
O2—Co1—N1—C20	115.76 (18)	C8—C5—C6—C7	179.0 (2)
O2—Co1—N1—C21	−72.6 (2)	C9—C10—C11—C12	179.5 (2)
O2—Co1—N3—C17	142.3 (2)	C9—C10—C15—C14	−178.9 (2)
O2—Co1—N3—C19	−46.1 (2)	C10—C11—C12—C13	−0.6 (4)
O2—C1—C2—C3	−172.60 (19)	C11—C10—C15—C14	1.0 (4)
O2—C1—C2—C7	7.8 (3)	C11—C12—C13—C14	0.9 (4)
O3—C9—C10—C11	−2.2 (3)	C11—C12—C13—C16	−177.3 (2)
O3—C9—C10—C15	177.7 (2)	C12—C13—C14—C15	−0.3 (4)
O4—Co1—O1—C1	−177.80 (12)	C13—C14—C15—C10	−0.6 (4)
O4—Co1—N1—C20	−57.83 (19)	C15—C10—C11—C12	−0.4 (4)
O4—Co1—N1—C21	113.8 (2)	C16—C13—C14—C15	178.0 (2)
O4—Co1—N3—C17	−44.1 (2)	C17—N3—C19—N4	−0.1 (3)
O4—Co1—N3—C19	127.5 (2)	C18—N4—C19—N3	0.1 (3)
O4—C9—C10—C11	177.4 (2)	C19—N3—C17—C18	0.1 (3)
O4—C9—C10—C15	−2.6 (3)	C19—N4—C18—C17	0.0 (3)
O1W—Co1—O1—C1	2.6 (2)	C20—N1—C21—C22	0.4 (3)
O1W—Co1—O2—C1	−176.39 (12)	C20—N2—C22—C21	0.2 (3)
O1W—Co1—O4—C9	178.9 (2)	C21—N1—C20—N2	−0.2 (3)
O1W—Co1—N1—C20	−148.24 (19)	C22—N2—C20—N1	0.0 (3)
O1W—Co1—N1—C21	23.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O1^i	0.85	1.96	2.780 (2)	163
O1W—H1W2···O3^i	0.85	1.94	2.761 (2)	163
N2—H7N···O3^ii	0.84	1.98	2.813 (3)	174
N4—H6N···O2^iii	0.84	2.03	2.866 (2)	170

Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+1, −z+2; (iii) −x+3/2, y−1/2, −z+3/2.