Literature DB >> 22719281

Bis[2-(2-amino-eth-yl)-1H-benzimidazole-κ(2)N(2),N(3)](nitrato-κ(2)O,O')cobalt(II) chloride trihydrate.

Abstract

In the title compound, [Co(NO(3))(C(9)H(11)N(3))(2)]Cl·3H(2)O, the Co(II) atom is coordinated by four N atoms from two chelating 2-(2-amino-eth-yl)-1H-benzimidazole ligands and two O atoms from one nitrate anion in a distorted octa-hedral coordination environment. In the crystal, N-H⋯Cl, N-H⋯O, O-H⋯Cl and O-H⋯O hydrogen bonds link the complex cations, chloride anions and solvent water mol-ecules into a three-dimensional network. π-π inter-actions between the imidazole and benzene rings and between the benzene rings are observed [centroid-centroid distances = 3.903 (3), 3.720 (3), 3.774 (3) and 3.926 (3) Å].

Entities: CellLine Chemical Disease Species

Year: 2012 PMID： 22719281 PMCID： PMC3379060 DOI： 10.1107/S1600536812018612

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For background to the coordination chemistry of benzimidazole and 2-substituted benzimidazole derivatives towards transition metal ions, see: Téllez et al. (2008 ▶). For the structures and properties of transition metal complexes with 2-(2-aminoethyl)benzimidazole, see: Dash et al. (1995 ▶); Zhang et al. (2008 ▶). For the synthesis of the 2-(2-aminoethyl)benzimidazole ligand, see: Cescon & Day (1962 ▶).

Experimental

Crystal data

[Co(NO3)(C9H11N3)2]Cl·3H2O M = 532.85 Triclinic, a = 7.408 (2) Å b = 9.808 (3) Å c = 17.280 (6) Å α = 76.238 (7)° β = 89.203 (7)° γ = 67.867 (5)° V = 1125.6 (6) Å3 Z = 2 Mo Kα radiation μ = 0.93 mm−1 T = 296 K 0.28 × 0.27 × 0.26 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.780, T max = 0.794 5677 measured reflections 3936 independent reflections 2895 reflections with I > 2σ(I) R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.050 wR(F 2) = 0.131 S = 0.99 3936 reflections 298 parameters 3 restraints H-atom parameters constrained Δρmax = 0.35 e Å−3 Δρmin = −0.86 e Å−3 Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812018612/hy2542sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018612/hy2542Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Co(NO₃)(C₉H₁₁N₃)₂]Cl·3H₂O	Z = 2
M_r = 532.85	F(000) = 554
Triclinic, P1	D_x = 1.572 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.408 (2) Å	Cell parameters from 1285 reflections
b = 9.808 (3) Å	θ = 2.9–23.7°
c = 17.280 (6) Å	µ = 0.93 mm⁻¹
α = 76.238 (7)°	T = 296 K
β = 89.203 (7)°	Cube, purple
γ = 67.867 (5)°	0.28 × 0.27 × 0.26 mm
V = 1125.6 (6) Å³

Bruker APEXII CCD diffractometer	3936 independent reflections
Radiation source: fine-focus sealed tube	2895 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
φ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.780, T_max = 0.794	k = −9→11
5677 measured reflections	l = −20→20

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0713P)²] where P = (F_o² + 2F_c²)/3
3936 reflections	(Δ/σ)_max = 0.001
298 parameters	Δρ_max = 0.35 e Å⁻³
3 restraints	Δρ_min = −0.86 e Å⁻³

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	U_iso*/U_eq
Co1	0.76176 (7)	0.51980 (6)	0.74870 (3)	0.01888 (18)
Cl1	1.08278 (18)	0.11248 (13)	0.14279 (7)	0.0416 (3)
C1	0.7611 (6)	0.4443 (5)	0.5882 (2)	0.0240 (9)
C2	0.7801 (6)	0.2936 (5)	0.6108 (3)	0.0324 (10)
H2A	0.7928	0.2425	0.6644	0.039*
C3	0.7796 (7)	0.2221 (6)	0.5509 (3)	0.0413 (12)
H3	0.7923	0.1211	0.5646	0.050*
C4	0.7604 (7)	0.2986 (6)	0.4698 (3)	0.0430 (12)
H4	0.7585	0.2476	0.4310	0.052*
C5	0.7445 (6)	0.4455 (6)	0.4467 (3)	0.0371 (11)
H5A	0.7321	0.4959	0.3929	0.045*
C6	0.7475 (6)	0.5175 (5)	0.5072 (2)	0.0291 (10)
C7	0.7441 (6)	0.6755 (5)	0.5797 (2)	0.0248 (9)
C8	0.7469 (7)	0.8163 (5)	0.5963 (3)	0.0361 (11)
H8A	0.6403	0.9022	0.5633	0.043*
H8B	0.8678	0.8260	0.5794	0.043*
C9	0.7298 (6)	0.8281 (5)	0.6815 (2)	0.0285 (10)
H9A	0.7666	0.9102	0.6877	0.034*
H9B	0.5949	0.8524	0.6939	0.034*
C10	0.6666 (6)	0.5948 (5)	0.9090 (2)	0.0239 (9)
C11	0.5304 (6)	0.7426 (5)	0.8863 (2)	0.0317 (10)
H11	0.4912	0.7924	0.8328	0.038*
C12	0.4541 (7)	0.8140 (6)	0.9470 (3)	0.0439 (13)
H12	0.3620	0.9134	0.9332	0.053*
C13	0.5108 (7)	0.7422 (6)	1.0267 (3)	0.0447 (13)
H13	0.4561	0.7941	1.0652	0.054*
C14	0.6464 (7)	0.5955 (6)	1.0504 (3)	0.0399 (12)
H14	0.6846	0.5462	1.1040	0.048*
C15	0.7235 (6)	0.5244 (5)	0.9898 (2)	0.0294 (10)
C16	0.8857 (6)	0.3640 (5)	0.9178 (2)	0.0265 (9)
C17	1.0300 (7)	0.2219 (5)	0.9025 (3)	0.0362 (11)
H17A	1.0044	0.1368	0.9349	0.043*
H17B	1.1595	0.2109	0.9203	0.043*
C18	1.0314 (7)	0.2116 (5)	0.8160 (3)	0.0336 (10)
H18A	1.1505	0.1298	0.8095	0.040*
H18B	0.9214	0.1882	0.8028	0.040*
N1	0.7582 (5)	0.5483 (4)	0.63286 (18)	0.0229 (7)
N2	0.7352 (5)	0.6619 (4)	0.50395 (19)	0.0317 (8)
H2	0.7239	0.7317	0.4612	0.038*
N3	0.8577 (5)	0.6833 (4)	0.73877 (18)	0.0249 (8)
H3B	0.8654	0.7008	0.7872	0.030*
H3C	0.9790	0.6530	0.7222	0.030*
N4	0.7730 (5)	0.4905 (4)	0.86430 (18)	0.0233 (8)
N5	0.8614 (5)	0.3800 (4)	0.9931 (2)	0.0346 (9)
H5	0.9212	0.3121	1.0359	0.042*
N6	1.0196 (4)	0.3571 (4)	0.76028 (19)	0.0247 (8)
H6A	1.0511	0.3406	0.7119	0.030*
H6B	1.1082	0.3872	0.7783	0.030*
N7	0.4435 (5)	0.5208 (4)	0.7462 (2)	0.0332 (8)
O1	0.6072 (4)	0.3975 (3)	0.75714 (15)	0.0238 (6)
O2	0.4853 (4)	0.6428 (3)	0.73689 (15)	0.0248 (6)
O3	0.2770 (4)	0.5211 (3)	0.74554 (16)	0.0325 (7)
O4	0.7163 (5)	0.8522 (4)	0.35574 (18)	0.0491 (9)
H1O4	0.6480	0.8549	0.3158	0.059*
H2O4	0.7584	0.9225	0.3391	0.059*
O5	0.4947 (5)	0.8627 (4)	0.2253 (2)	0.0512 (9)
H1O5	0.4095	0.9325	0.1902	0.061*
H2O5	0.4738	0.7817	0.2302	0.061*
O6	0.1492 (5)	0.9162 (4)	0.7010 (2)	0.0515 (9)
H1O6	0.2360	0.8278	0.7051	0.062*
H2O6	0.0865	0.9132	0.7425	0.062*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0188 (3)	0.0192 (3)	0.0200 (3)	−0.0091 (2)	0.0009 (2)	−0.0046 (2)
Cl1	0.0477 (7)	0.0351 (7)	0.0390 (7)	−0.0174 (6)	−0.0086 (5)	−0.0009 (5)
C1	0.022 (2)	0.030 (2)	0.022 (2)	−0.0093 (19)	0.0009 (17)	−0.0119 (18)
C2	0.039 (3)	0.032 (2)	0.031 (2)	−0.017 (2)	0.005 (2)	−0.011 (2)
C3	0.050 (3)	0.036 (3)	0.048 (3)	−0.020 (2)	0.004 (2)	−0.022 (2)
C4	0.049 (3)	0.054 (3)	0.040 (3)	−0.027 (3)	0.005 (2)	−0.028 (3)
C5	0.037 (3)	0.059 (3)	0.023 (2)	−0.022 (2)	0.0043 (19)	−0.017 (2)
C6	0.021 (2)	0.037 (3)	0.027 (2)	−0.010 (2)	0.0001 (18)	−0.007 (2)
C7	0.028 (2)	0.028 (2)	0.020 (2)	−0.0139 (19)	0.0017 (17)	−0.0045 (18)
C8	0.048 (3)	0.028 (2)	0.032 (2)	−0.017 (2)	0.005 (2)	−0.001 (2)
C9	0.032 (2)	0.018 (2)	0.033 (2)	−0.0085 (19)	−0.0006 (19)	−0.0039 (18)
C10	0.024 (2)	0.029 (2)	0.025 (2)	−0.0147 (19)	0.0019 (17)	−0.0097 (18)
C11	0.036 (3)	0.030 (2)	0.026 (2)	−0.009 (2)	0.0018 (19)	−0.0075 (19)
C12	0.036 (3)	0.049 (3)	0.050 (3)	−0.012 (3)	0.011 (2)	−0.028 (3)
C13	0.046 (3)	0.069 (4)	0.037 (3)	−0.028 (3)	0.019 (2)	−0.036 (3)
C14	0.046 (3)	0.064 (4)	0.020 (2)	−0.030 (3)	0.007 (2)	−0.016 (2)
C15	0.036 (3)	0.039 (3)	0.021 (2)	−0.023 (2)	0.0021 (18)	−0.0062 (19)
C16	0.031 (2)	0.028 (2)	0.024 (2)	−0.018 (2)	−0.0026 (18)	−0.0012 (18)
C17	0.037 (3)	0.025 (2)	0.035 (3)	−0.006 (2)	−0.009 (2)	0.006 (2)
C18	0.032 (2)	0.023 (2)	0.041 (3)	−0.009 (2)	0.005 (2)	−0.003 (2)
N1	0.0239 (18)	0.0219 (18)	0.0241 (18)	−0.0094 (15)	0.0024 (14)	−0.0071 (15)
N2	0.041 (2)	0.032 (2)	0.0208 (18)	−0.0159 (18)	0.0025 (16)	−0.0005 (16)
N3	0.0266 (19)	0.0244 (19)	0.0246 (18)	−0.0107 (16)	0.0009 (14)	−0.0064 (15)
N4	0.0250 (19)	0.0222 (18)	0.0219 (17)	−0.0082 (16)	−0.0014 (14)	−0.0055 (15)
N5	0.041 (2)	0.037 (2)	0.0193 (18)	−0.0133 (19)	−0.0047 (16)	0.0021 (16)
N6	0.0179 (17)	0.0263 (19)	0.0310 (19)	−0.0096 (15)	0.0020 (14)	−0.0075 (15)
N7	0.0252 (12)	0.0359 (15)	0.043 (2)	−0.0149 (11)	0.0013 (16)	−0.0121 (18)
O1	0.0239 (13)	0.0269 (14)	0.0258 (14)	−0.0155 (10)	0.0026 (12)	−0.0062 (12)
O2	0.0180 (14)	0.0258 (15)	0.0295 (15)	−0.0068 (12)	0.0002 (12)	−0.0075 (13)
O3	0.0229 (14)	0.0463 (19)	0.0324 (16)	−0.0175 (14)	0.0022 (13)	−0.0103 (14)
O4	0.064 (2)	0.050 (2)	0.0339 (18)	−0.0329 (19)	−0.0067 (16)	0.0074 (16)
O5	0.050 (2)	0.037 (2)	0.064 (2)	−0.0182 (18)	−0.0146 (18)	−0.0055 (17)
O6	0.047 (2)	0.037 (2)	0.059 (2)	−0.0079 (17)	0.0078 (17)	−0.0037 (17)

Co1—O1	1.928 (3)	C12—C13	1.379 (7)
Co1—O2	1.930 (3)	C12—H12	0.9300
Co1—N4	1.948 (3)	C13—C14	1.375 (7)
Co1—N6	1.949 (3)	C13—H13	0.9300
Co1—N1	1.953 (3)	C14—C15	1.392 (6)
Co1—N3	1.957 (3)	C14—H14	0.9300
C1—C2	1.388 (6)	C15—N5	1.388 (6)
C1—C6	1.400 (6)	C16—N4	1.337 (5)
C1—N1	1.412 (5)	C16—N5	1.349 (5)
C2—C3	1.383 (6)	C16—C17	1.483 (6)
C2—H2A	0.9300	C17—C18	1.521 (6)
C3—C4	1.404 (7)	C17—H17A	0.9700
C3—H3	0.9300	C17—H17B	0.9700
C4—C5	1.360 (7)	C18—N6	1.491 (5)
C4—H4	0.9300	C18—H18A	0.9700
C5—C6	1.399 (6)	C18—H18B	0.9700
C5—H5A	0.9300	N2—H2	0.8600
C6—N2	1.372 (5)	N3—H3B	0.9000
C7—N1	1.331 (5)	N3—H3C	0.9000
C7—N2	1.351 (5)	N5—H5	0.8600
C7—C8	1.484 (6)	N6—H6A	0.9000
C8—C9	1.504 (5)	N6—H6B	0.9000
C8—H8A	0.9700	N7—O3	1.233 (4)
C8—H8B	0.9700	N7—O2	1.319 (4)
C9—N3	1.496 (5)	N7—O1	1.327 (4)
C9—H9A	0.9700	O4—H1O4	0.8500
C9—H9B	0.9700	O4—H2O4	0.8496
C10—C11	1.383 (6)	O5—H1O5	0.8501
C10—C15	1.394 (5)	O5—H2O5	0.8500
C10—N4	1.419 (5)	O6—H1O6	0.8500
C11—C12	1.394 (6)	O6—H2O6	0.8499
C11—H11	0.9300

O1—Co1—O2	68.37 (12)	C14—C13—C12	121.3 (4)
O1—Co1—N4	89.76 (12)	C14—C13—H13	119.3
O2—Co1—N4	92.05 (12)	C12—C13—H13	119.3
O1—Co1—N6	98.11 (13)	C13—C14—C15	116.5 (4)
O2—Co1—N6	166.39 (13)	C13—C14—H14	121.7
N4—Co1—N6	89.37 (14)	C15—C14—H14	121.7
O1—Co1—N1	91.42 (12)	N5—C15—C14	131.0 (4)
O2—Co1—N1	89.38 (12)	N5—C15—C10	106.1 (3)
N4—Co1—N1	178.40 (14)	C14—C15—C10	122.9 (4)
N6—Co1—N1	89.40 (13)	N4—C16—N5	111.3 (4)
O1—Co1—N3	166.29 (13)	N4—C16—C17	128.0 (4)
O2—Co1—N3	97.97 (13)	N5—C16—C17	120.6 (4)
N4—Co1—N3	89.66 (13)	C16—C17—C18	115.8 (3)
N6—Co1—N3	95.58 (14)	C16—C17—H17A	108.3
N1—Co1—N3	89.44 (13)	C18—C17—H17A	108.3
C2—C1—C6	120.0 (4)	C16—C17—H17B	108.3
C2—C1—N1	132.3 (4)	C18—C17—H17B	108.3
C6—C1—N1	107.7 (4)	H17A—C17—H17B	107.4
C3—C2—C1	117.8 (4)	N6—C18—C17	111.2 (3)
C3—C2—H2A	121.1	N6—C18—H18A	109.4
C1—C2—H2A	121.1	C17—C18—H18A	109.4
C2—C3—C4	121.4 (5)	N6—C18—H18B	109.4
C2—C3—H3	119.3	C17—C18—H18B	109.4
C4—C3—H3	119.3	H18A—C18—H18B	108.0
C5—C4—C3	121.5 (4)	C7—N1—C1	106.1 (3)
C5—C4—H4	119.2	C7—N1—Co1	125.7 (3)
C3—C4—H4	119.2	C1—N1—Co1	128.2 (3)
C4—C5—C6	117.2 (4)	C7—N2—C6	108.1 (3)
C4—C5—H5A	121.4	C7—N2—H2	125.9
C6—C5—H5A	121.4	C6—N2—H2	125.9
N2—C6—C5	131.4 (4)	C9—N3—Co1	112.9 (2)
N2—C6—C1	106.5 (3)	C9—N3—H3B	109.0
C5—C6—C1	122.0 (4)	Co1—N3—H3B	109.0
N1—C7—N2	111.6 (4)	C9—N3—H3C	109.0
N1—C7—C8	127.2 (3)	Co1—N3—H3C	109.0
N2—C7—C8	121.1 (4)	H3B—N3—H3C	107.8
C7—C8—C9	116.8 (4)	C16—N4—C10	106.1 (3)
C7—C8—H8A	108.1	C16—N4—Co1	125.6 (3)
C9—C8—H8A	108.1	C10—N4—Co1	128.3 (3)
C7—C8—H8B	108.1	C16—N5—C15	108.5 (3)
C9—C8—H8B	108.1	C16—N5—H5	125.8
H8A—C8—H8B	107.3	C15—N5—H5	125.8
N3—C9—C8	111.6 (3)	C18—N6—Co1	113.3 (2)
N3—C9—H9A	109.3	C18—N6—H6A	108.9
C8—C9—H9A	109.3	Co1—N6—H6A	108.9
N3—C9—H9B	109.3	C18—N6—H6B	108.9
C8—C9—H9B	109.3	Co1—N6—H6B	108.9
H9A—C9—H9B	108.0	H6A—N6—H6B	107.7
C11—C10—C15	119.7 (4)	O3—N7—O2	125.0 (4)
C11—C10—N4	132.3 (4)	O3—N7—O1	125.0 (4)
C15—C10—N4	108.0 (4)	O2—N7—O1	110.0 (3)
C10—C11—C12	117.4 (4)	N7—O1—Co1	90.7 (2)
C10—C11—H11	121.3	N7—O2—Co1	90.9 (2)
C12—C11—H11	121.3	H1O4—O4—H2O4	104.9
C13—C12—C11	122.1 (5)	H1O5—O5—H2O5	107.7
C13—C12—H12	118.9	H1O6—O6—H2O6	107.7
C11—C12—H12	118.9

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4	0.86	1.91	2.757 (5)	168
N3—H3B···Cl1ⁱ	0.90	2.56	3.322 (3)	143
N3—H3C···O3ⁱⁱ	0.90	2.08	2.897 (4)	150
N5—H5···Cl1ⁱⁱⁱ	0.86	2.29	3.148 (4)	174
N6—H6A···O4ⁱ	0.90	2.54	3.299 (5)	142
N6—H6B···O3ⁱⁱ	0.90	2.12	2.897 (4)	145
O4—H1O4···O5	0.85	1.92	2.766 (4)	179
O4—H2O4···O6^iv	0.85	1.93	2.781 (5)	179
O5—H1O5···Cl1^v	0.85	2.41	3.189 (3)	153
O5—H2O5···O1^vi	0.85	2.03	2.872 (4)	174
O6—H1O6···O2	0.85	2.01	2.828 (4)	162
O6—H2O6···Cl1^vi	0.85	2.34	3.192 (4)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O4	0.86	1.91	2.757 (5)	168
N3—H3B⋯Cl1ⁱ	0.90	2.56	3.322 (3)	143
N3—H3C⋯O3ⁱⁱ	0.90	2.08	2.897 (4)	150
N5—H5⋯Cl1ⁱⁱⁱ	0.86	2.29	3.148 (4)	174
N6—H6A⋯O4ⁱ	0.90	2.54	3.299 (5)	142
N6—H6B⋯O3ⁱⁱ	0.90	2.12	2.897 (4)	145
O4—H1O4⋯O5	0.85	1.92	2.766 (4)	179
O4—H2O4⋯O6^iv	0.85	1.93	2.781 (5)	179
O5—H1O5⋯Cl1^v	0.85	2.41	3.189 (3)	153
O5—H2O5⋯O1^vi	0.85	2.03	2.872 (4)	174
O6—H1O6⋯O2	0.85	2.01	2.828 (4)	162
O6—H2O6⋯Cl1^vi	0.85	2.34	3.192 (4)	176

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

2 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. Bis[2-(2-amino-ethyl)-1H-benzimidazole-κN,N]zinc(II) bis-(perchlorate).

Authors: Jine Zhang; Yanping Li; Fangjun Huo; Zhigang Zhang
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2007-12-12

2 in total