Bis(benzimidazole)bis­(4-hydroxy­benzoato)cobalt(II) 0.25-hydrate

In the title compound, [Co(C₇H₅O₃)₂(C₇H₆N₂)₂]·0.25H₂O, the Co^II atom is coordinated by two 4-hydroxy­benzoate (hbz) anions and two benzimidazole (bzim) ligands in a distorted trigonal–bipyramidal geometry. The carboxylate group of one of the hbz anions chelates to the Co atom with a normal Co—O bond [1.993 (2) Å] and a longer Co—O bond [2.561 (3) Å]. Aromatic π–π stacking is observed between neighbouring bzim ligands but not between hbz ligands.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.006 Å
• Disorder in solvent or counterion
• R factor = 0.042
• wR factor = 0.115
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.12 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.51 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C34
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C35
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      25.00 Perc.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      33.20 Deg.
              O1W  -O1W  -H1B     2.655   1.555   1.555

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Bis(benzimidazole)bis(4-hydroxybenzoato)cobalt(II) 0.25-hydrate

Crystal data

[Co(C7H5O3)2(C7H6N2)2]·0.25H2O	F(000) = 2364
Mr = 573.93	Dx = 1.456 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 11022 reflections
a = 12.952 (5) Å	θ = 2.0–24.0°
b = 27.564 (11) Å	µ = 0.71 mm^−1
c = 15.147 (6) Å	T = 295 K
β = 104.499 (6)°	Prism, red
V = 5235 (4) Å^3	0.32 × 0.30 × 0.22 mm
Z = 8

Data collection

Rigaku R-AXIS RAPID diffractometer	4745 independent reflections
Radiation source: fine-focus sealed tube	2922 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 10.00 pixels mm^-1	θmax = 25.2°, θmin = 1.8°
ω scans	h = −15→15
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −28→33
Tmin = 0.782, Tmax = 0.862	l = −14→18
13970 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)] = 0.042	Hydrogen site location: difmap and geom
wR(F^2) = 0.115	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0448P)^2 + 6.148P] where P = (Fo^2 + 2Fc^2)/3
4745 reflections	(Δ/σ)max = 0.001
361 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Co	0.77755 (3)	0.621457 (16)	0.57387 (3)	0.04308 (16)
O1	0.66884 (18)	0.58912 (8)	0.47742 (16)	0.0550 (7)
O2	0.54833 (19)	0.64793 (8)	0.44076 (17)	0.0570 (7)
O3	0.28053 (19)	0.46595 (9)	0.25458 (18)	0.0702 (8)
H3A	0.2980	0.4373	0.2764	0.084*
O4	0.70252 (18)	0.62541 (8)	0.67355 (15)	0.0517 (6)
O5	0.85718 (19)	0.66134 (9)	0.72868 (17)	0.0582 (7)
O6	0.6488 (2)	0.68389 (10)	1.06363 (17)	0.0682 (8)
H6A	0.5797	0.6730	1.0553	0.082*
N11	1.0569 (2)	0.54214 (12)	0.6568 (2)	0.0737 (10)
H11	1.1240	0.5415	0.6830	0.088*
N13	0.8964 (2)	0.57168 (10)	0.60024 (18)	0.0458 (7)
N21	0.8943 (2)	0.75534 (10)	0.5141 (2)	0.0602 (9)
H21	0.9181	0.7840	0.5301	0.072*
N23	0.8325 (2)	0.68140 (10)	0.5248 (2)	0.0479 (7)
C12	0.9954 (3)	0.58166 (14)	0.6424 (3)	0.0607 (11)
H12	1.0200	0.6127	0.6602	0.073*
C14	0.8117 (3)	0.49086 (14)	0.5457 (3)	0.0796 (14)
H14	0.7432	0.5026	0.5211	0.096*
C15	0.8346 (4)	0.44227 (16)	0.5425 (4)	0.0997 (18)
H15	0.7804	0.4210	0.5148	0.120*
C16	0.9352 (4)	0.42423 (16)	0.5793 (4)	0.0925 (16)
H16	0.9474	0.3911	0.5763	0.111*
C17	1.0167 (4)	0.45373 (16)	0.6197 (3)	0.0806 (14)
H17	1.0847	0.4416	0.6444	0.097*
C18	0.9949 (3)	0.50260 (14)	0.6227 (3)	0.0581 (10)
C19	0.8936 (3)	0.52144 (12)	0.5865 (2)	0.0490 (9)
C22	0.8670 (3)	0.72215 (13)	0.5681 (3)	0.0550 (10)
H22	0.8718	0.7271	0.6297	0.066*
C24	0.8102 (3)	0.65919 (13)	0.3594 (3)	0.0586 (10)
H24	0.7838	0.6281	0.3631	0.070*
C25	0.8237 (3)	0.67724 (17)	0.2791 (3)	0.0736 (12)
H25	0.8056	0.6579	0.2273	0.088*
C26	0.8637 (4)	0.72351 (17)	0.2722 (3)	0.0773 (13)
H26	0.8716	0.7343	0.2161	0.093*
C27	0.8915 (3)	0.75339 (15)	0.3465 (3)	0.0692 (12)
H27	0.9186	0.7843	0.3423	0.083*
C28	0.8778 (3)	0.73569 (12)	0.4281 (3)	0.0498 (9)
C29	0.8374 (3)	0.68915 (12)	0.4349 (2)	0.0456 (9)
C31	0.5765 (3)	0.60463 (12)	0.4380 (2)	0.0427 (8)
C32	0.4993 (3)	0.56828 (11)	0.3867 (2)	0.0399 (8)
C33	0.4053 (3)	0.58153 (13)	0.3274 (3)	0.0622 (11)
H33	0.3896	0.6143	0.3170	0.075*
C34	0.3341 (3)	0.54758 (14)	0.2833 (3)	0.0751 (13)
H34	0.2712	0.5574	0.2427	0.090*
C35	0.3545 (3)	0.49921 (12)	0.2982 (2)	0.0482 (9)
C36	0.4475 (3)	0.48484 (13)	0.3551 (3)	0.0570 (10)
H36	0.4627	0.4520	0.3650	0.068*
C37	0.5197 (3)	0.51946 (13)	0.3983 (3)	0.0597 (11)
H37	0.5841	0.5094	0.4365	0.072*
C41	0.7699 (3)	0.64823 (12)	0.7381 (2)	0.0472 (9)
C42	0.7376 (3)	0.65688 (11)	0.8241 (2)	0.0434 (8)
C43	0.8040 (3)	0.68169 (12)	0.8963 (2)	0.0503 (9)
H43	0.8700	0.6928	0.8908	0.060*
C44	0.7737 (3)	0.69008 (12)	0.9756 (3)	0.0546 (10)
H44	0.8193	0.7064	1.0236	0.066*
C45	0.6755 (3)	0.67425 (13)	0.9841 (2)	0.0506 (9)
C46	0.6082 (3)	0.64954 (13)	0.9131 (3)	0.0521 (9)
H46	0.5420	0.6387	0.9184	0.063*
C47	0.6401 (3)	0.64114 (13)	0.8349 (3)	0.0524 (9)
H47	0.5948	0.6243	0.7875	0.063*
O1W	0.4431 (15)	0.7198 (7)	0.2637 (13)	0.191 (10)	0.25
H1A	0.4768	0.6987	0.3150	0.287*	0.25
H1B	0.4806	0.7109	0.2207	0.287*	0.25

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co	0.0374 (3)	0.0341 (3)	0.0531 (3)	−0.0047 (2)	0.0026 (2)	−0.0055 (2)
O1	0.0457 (15)	0.0461 (15)	0.0650 (16)	−0.0081 (12)	−0.0015 (12)	−0.0085 (12)
O2	0.0553 (16)	0.0367 (14)	0.0770 (18)	−0.0088 (12)	0.0130 (13)	−0.0127 (13)
O3	0.0546 (16)	0.0393 (14)	0.097 (2)	−0.0111 (12)	−0.0179 (14)	−0.0051 (14)
O4	0.0502 (15)	0.0478 (14)	0.0536 (14)	−0.0032 (12)	0.0062 (12)	−0.0068 (12)
O5	0.0446 (15)	0.0613 (17)	0.0701 (17)	−0.0003 (13)	0.0172 (13)	0.0031 (13)
O6	0.0755 (19)	0.0727 (19)	0.0588 (17)	−0.0110 (15)	0.0214 (14)	−0.0113 (14)
N11	0.0368 (18)	0.064 (2)	0.105 (3)	0.0092 (17)	−0.0115 (17)	−0.022 (2)
N13	0.0360 (16)	0.0407 (17)	0.0551 (18)	−0.0030 (13)	0.0009 (13)	−0.0087 (14)
N21	0.066 (2)	0.0324 (17)	0.081 (2)	−0.0174 (15)	0.0162 (18)	−0.0103 (17)
N23	0.0456 (17)	0.0367 (16)	0.060 (2)	−0.0071 (13)	0.0102 (14)	−0.0069 (14)
C12	0.045 (2)	0.051 (2)	0.077 (3)	−0.0011 (19)	−0.0009 (19)	−0.016 (2)
C14	0.048 (2)	0.050 (3)	0.128 (4)	0.000 (2)	−0.002 (2)	−0.022 (3)
C15	0.071 (3)	0.049 (3)	0.162 (5)	−0.004 (2)	−0.002 (3)	−0.030 (3)
C16	0.089 (4)	0.045 (3)	0.133 (4)	0.010 (3)	0.009 (3)	−0.020 (3)
C17	0.065 (3)	0.061 (3)	0.104 (4)	0.020 (2)	−0.002 (3)	−0.014 (3)
C18	0.049 (2)	0.052 (2)	0.066 (3)	0.0072 (19)	0.0025 (19)	−0.014 (2)
C19	0.043 (2)	0.042 (2)	0.060 (2)	0.0027 (16)	0.0087 (17)	−0.0096 (18)
C22	0.056 (2)	0.044 (2)	0.065 (2)	−0.0133 (18)	0.0130 (19)	−0.0136 (19)
C24	0.065 (3)	0.042 (2)	0.066 (3)	−0.0055 (19)	0.011 (2)	−0.006 (2)
C25	0.084 (3)	0.075 (3)	0.058 (3)	−0.014 (3)	0.011 (2)	−0.010 (2)
C26	0.084 (3)	0.081 (3)	0.066 (3)	−0.005 (3)	0.016 (2)	0.014 (3)
C27	0.073 (3)	0.053 (3)	0.081 (3)	−0.008 (2)	0.018 (2)	0.013 (2)
C28	0.044 (2)	0.038 (2)	0.064 (3)	−0.0006 (16)	0.0070 (18)	−0.0015 (19)
C29	0.0387 (19)	0.0343 (19)	0.061 (2)	−0.0006 (15)	0.0069 (17)	−0.0004 (17)
C31	0.044 (2)	0.040 (2)	0.044 (2)	−0.0087 (16)	0.0119 (16)	−0.0070 (16)
C32	0.0393 (19)	0.0360 (19)	0.044 (2)	−0.0078 (15)	0.0103 (15)	−0.0040 (15)
C33	0.056 (2)	0.0303 (19)	0.085 (3)	0.0006 (17)	−0.011 (2)	−0.0004 (19)
C34	0.056 (2)	0.048 (2)	0.096 (3)	−0.001 (2)	−0.029 (2)	0.003 (2)
C35	0.042 (2)	0.039 (2)	0.058 (2)	−0.0071 (16)	0.0017 (17)	−0.0069 (17)
C36	0.050 (2)	0.0301 (19)	0.081 (3)	−0.0016 (16)	−0.0023 (19)	0.0006 (18)
C37	0.040 (2)	0.044 (2)	0.080 (3)	−0.0025 (17)	−0.0122 (18)	−0.004 (2)
C41	0.047 (2)	0.0351 (19)	0.057 (2)	0.0081 (17)	0.0090 (18)	0.0026 (17)
C42	0.0394 (19)	0.0337 (18)	0.053 (2)	0.0036 (15)	0.0032 (16)	0.0018 (16)
C43	0.044 (2)	0.041 (2)	0.061 (2)	−0.0042 (16)	0.0063 (18)	−0.0027 (18)
C44	0.058 (2)	0.044 (2)	0.055 (2)	−0.0060 (18)	0.0017 (19)	−0.0092 (18)
C45	0.058 (2)	0.043 (2)	0.050 (2)	0.0027 (18)	0.0100 (18)	0.0033 (18)
C46	0.045 (2)	0.051 (2)	0.060 (2)	−0.0042 (18)	0.0118 (18)	−0.0001 (19)
C47	0.046 (2)	0.051 (2)	0.056 (2)	−0.0022 (18)	0.0038 (18)	−0.0042 (18)
O1W	0.21 (2)	0.21 (2)	0.123 (15)	−0.049 (15)	−0.017 (16)	0.088 (15)

Geometric parameters (Å, º)

Co—O1	1.970 (2)	C24—C25	1.365 (5)
Co—O4	1.993 (2)	C24—C29	1.383 (5)
Co—O5	2.561 (3)	C24—H24	0.9300
Co—N13	2.026 (3)	C25—C26	1.390 (6)
Co—N23	2.013 (3)	C25—H25	0.9300
Co—O2	3.227 (3)	C26—C27	1.369 (6)
O1—C31	1.269 (4)	C26—H26	0.9300
O2—C31	1.252 (4)	C27—C28	1.380 (5)
O3—C35	1.371 (4)	C27—H27	0.9300
O3—H3A	0.8637	C28—C29	1.399 (5)
O4—C41	1.298 (4)	C31—C32	1.489 (4)
O5—C41	1.228 (4)	C32—C33	1.370 (4)
O6—C45	1.359 (4)	C32—C37	1.374 (4)
O6—H6A	0.9231	C33—C34	1.365 (5)
N11—C12	1.335 (4)	C33—H33	0.9300
N11—C18	1.376 (5)	C34—C35	1.367 (5)
N11—H11	0.8600	C34—H34	0.9300
N13—C12	1.311 (4)	C35—C36	1.353 (5)
N13—C19	1.400 (4)	C36—C37	1.380 (5)
N21—C22	1.333 (4)	C36—H36	0.9300
N21—C28	1.377 (4)	C37—H37	0.9300
N21—H21	0.8600	C41—C42	1.484 (5)
N23—C22	1.320 (4)	C42—C47	1.383 (5)
N23—C29	1.395 (4)	C42—C43	1.390 (5)
C12—H12	0.9300	C43—C44	1.375 (5)
C14—C19	1.374 (5)	C43—H43	0.9300
C14—C15	1.375 (5)	C44—C45	1.381 (5)
C14—H14	0.9300	C44—H44	0.9300
C15—C16	1.376 (6)	C45—C46	1.383 (5)
C15—H15	0.9300	C46—C47	1.368 (5)
C16—C17	1.351 (6)	C46—H46	0.9300
C16—H16	0.9300	C47—H47	0.9300
C17—C18	1.379 (5)	O1W—O1W^i	1.63 (4)
C17—H17	0.9300	O1W—H1A	0.9808
C18—C19	1.390 (5)	O1W—H1B	0.9387
C22—H22	0.9300
O1—Co—O4	101.13 (10)	C27—C26—H26	119.5
O1—Co—O5	157.27 (10)	C25—C26—H26	119.5
O1—Co—N13	101.91 (11)	C26—C27—C28	117.2 (4)
O1—Co—N23	110.53 (11)	C26—C27—H27	121.4
O4—Co—O5	56.20 (9)	C28—C27—H27	121.4
O4—Co—N13	112.23 (11)	N21—C28—C27	133.1 (4)
O4—Co—N23	121.29 (11)	N21—C28—C29	105.2 (3)
O5—Co—N13	89.90 (9)	C27—C28—C29	121.7 (4)
O5—Co—N23	83.52 (10)	C24—C29—N23	130.7 (3)
N13—Co—N23	107.89 (12)	C24—C29—C28	120.6 (4)
C31—O1—Co	127.7 (2)	N23—C29—C28	108.8 (3)
C35—O3—H3A	110.1	O2—C31—O1	123.6 (3)
C41—O4—Co	103.5 (2)	O2—C31—C32	119.7 (3)
C45—O6—H6A	105.6	O1—C31—C32	116.7 (3)
C12—N11—C18	108.5 (3)	C33—C32—C37	117.1 (3)
C12—N11—H11	125.8	C33—C32—C31	122.2 (3)
C18—N11—H11	125.8	C37—C32—C31	120.6 (3)
C12—N13—C19	105.4 (3)	C34—C33—C32	121.3 (3)
C12—N13—Co	123.8 (2)	C34—C33—H33	119.4
C19—N13—Co	130.6 (2)	C32—C33—H33	119.4
C22—N21—C28	108.0 (3)	C33—C34—C35	120.5 (3)
C22—N21—H21	126.0	C33—C34—H34	119.7
C28—N21—H21	126.0	C35—C34—H34	119.7
C22—N23—C29	105.2 (3)	C36—C35—C34	119.7 (3)
C22—N23—Co	128.5 (3)	C36—C35—O3	121.0 (3)
C29—N23—Co	126.3 (2)	C34—C35—O3	119.3 (3)
N13—C12—N11	112.3 (3)	C35—C36—C37	119.2 (3)
N13—C12—H12	123.8	C35—C36—H36	120.4
N11—C12—H12	123.8	C37—C36—H36	120.4
C19—C14—C15	117.7 (4)	C32—C37—C36	122.0 (3)
C19—C14—H14	121.2	C32—C37—H37	119.0
C15—C14—H14	121.2	C36—C37—H37	119.0
C14—C15—C16	121.9 (4)	O5—C41—O4	121.3 (3)
C14—C15—H15	119.1	O5—C41—C42	121.6 (3)
C16—C15—H15	119.1	O4—C41—C42	117.0 (3)
C17—C16—C15	121.3 (4)	C47—C42—C43	117.7 (3)
C17—C16—H16	119.4	C47—C42—C41	121.4 (3)
C15—C16—H16	119.4	C43—C42—C41	120.9 (3)
C16—C17—C18	117.4 (4)	C44—C43—C42	121.0 (3)
C16—C17—H17	121.3	C44—C43—H43	119.5
C18—C17—H17	121.3	C42—C43—H43	119.5
N11—C18—C17	132.9 (4)	C43—C44—C45	120.0 (3)
N11—C18—C19	104.9 (3)	C43—C44—H44	120.0
C17—C18—C19	122.2 (4)	C45—C44—H44	120.0
C14—C19—C18	119.6 (3)	O6—C45—C44	117.7 (3)
C14—C19—N13	131.5 (3)	O6—C45—C46	122.4 (3)
C18—C19—N13	108.9 (3)	C44—C45—C46	119.9 (4)
N23—C22—N21	112.8 (3)	C47—C46—C45	119.3 (3)
N23—C22—H22	123.6	C47—C46—H46	120.4
N21—C22—H22	123.6	C45—C46—H46	120.4
C25—C24—C29	117.1 (4)	C46—C47—C42	122.2 (3)
C25—C24—H24	121.4	C46—C47—H47	118.9
C29—C24—H24	121.4	C42—C47—H47	118.9
C24—C25—C26	122.4 (4)	O1W^i—O1W—H1A	87.1
C24—C25—H25	118.8	O1W^i—O1W—H1B	33.2
C26—C25—H25	118.8	H1A—O1W—H1B	100.9
C27—C26—C25	121.1 (4)

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
O1W—H1A···O2	0.98	2.36	3.339 (19)	177
O3—H3A···O4^ii	0.86	1.89	2.730 (4)	164
O6—H6A···O2^iii	0.92	1.81	2.724 (4)	170
N11—H11···O3^iv	0.86	2.06	2.913 (4)	174
N21—H21···O2^v	0.86	1.95	2.806 (4)	172

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