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The title compound, [NiCl2(C11H14N2O)2], was synthesized from 1-(2-ethoxy­ethyl)­benz­imidazole and nickel dichloride in ethanol and is isostructural with its cobalt analogue. It shows a distorted tetrahedral geometry about NiII, involving two Cl atoms and two benz­imidazole N atoms. The crystal structure is stabilized by C—H...Cl and C—H...O interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804031356/hb6130sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804031356/hb6130Isup2.hkl
Contains datablock I

CCDC reference: 262235

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.027
  • wR factor = 0.069
  • Data-to-parameter ratio = 18.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.74 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.39 Ratio
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.15 From the CIF: _reflns_number_total 5171 Count of symmetry unique reflns 2691 Completeness (_total/calc) 192.16% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2480 Fraction of Friedel pairs measured 0.922 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Dichlorobis[1-(2-ethoxyethyl)-1H-benzimidazole-κN3]nickel(II) top
Crystal data top
[NiCl2(C11H14N2O)2]F(000) = 1064
Mr = 510.07Dx = 1.444 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 40494 reflections
a = 17.416 (5) Åθ = 1.6–27.3°
b = 7.624 (5) ŵ = 1.08 mm1
c = 17.667 (5) ÅT = 100 K
V = 2345.8 (18) Å3Prism, violet
Z = 40.32 × 0.31 × 0.30 mm
Data collection top
Stoe IPDS-II
diffractometer
4987 reflections with I > 2σ(I
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focusRint = 0.056
Plane graphite monochromatorθmax = 27.2°, θmin = 2.3°
Detector resolution: 6.67 pixels mm-1h = 2222
ω scansk = 99
25872 measured reflectionsl = 2222
5171 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.027H-atom parameters constrained
wR(F2) = 0.069 w = 1/[σ2(Fo2) + (0.0495P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
5171 reflectionsΔρmax = 0.38 e Å3
280 parametersΔρmin = 0.77 e Å3
1 restraintAbsolute structure: Flack (1983). 2480 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.079 (9)
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 (Å2) top
xyzUiso*/Ueq
Ni10.44607 (1)0.87640 (3)0.86786 (2)0.0164 (1)
Cl10.53111 (3)0.70127 (6)0.81115 (3)0.0209 (1)
Cl20.42115 (3)1.16157 (6)0.84841 (3)0.0246 (1)
O10.29918 (8)0.99934 (18)1.15516 (9)0.0234 (4)
O20.26299 (10)0.4927 (2)0.65727 (10)0.0329 (5)
N10.45887 (10)0.8502 (2)0.97869 (10)0.0190 (4)
N20.45275 (10)0.9167 (2)1.10100 (10)0.0207 (5)
N30.34843 (9)0.7497 (2)0.85268 (9)0.0185 (4)
N40.26617 (9)0.5436 (2)0.81845 (10)0.0206 (4)
C10.48414 (11)0.7052 (2)1.02009 (11)0.0185 (5)
C20.51009 (12)0.5408 (3)0.99643 (12)0.0238 (5)
C30.53278 (14)0.4246 (3)1.05239 (12)0.0274 (6)
C40.52997 (13)0.4692 (3)1.12958 (12)0.0271 (6)
C50.50342 (12)0.6299 (3)1.15361 (12)0.0235 (6)
C60.48087 (11)0.7461 (3)1.09732 (11)0.0198 (5)
C70.44072 (11)0.9705 (3)1.02974 (12)0.0200 (5)
C80.43516 (12)1.0125 (3)1.17017 (12)0.0240 (6)
C90.36007 (12)0.9551 (3)1.20487 (11)0.0231 (5)
C100.22636 (12)0.9512 (3)1.18660 (12)0.0247 (6)
C110.16395 (14)1.0118 (4)1.13445 (16)0.0363 (7)
C120.27538 (10)0.8025 (2)0.87541 (12)0.0180 (5)
C130.25020 (12)0.9554 (3)0.91149 (11)0.0224 (5)
C140.17226 (12)0.9710 (3)0.92496 (12)0.0239 (5)
C150.12086 (12)0.8382 (3)0.90348 (12)0.0238 (6)
C160.14425 (11)0.6878 (2)0.86769 (13)0.0226 (5)
C170.22299 (11)0.6727 (2)0.85397 (11)0.0199 (5)
C180.33967 (11)0.5972 (2)0.81937 (12)0.0196 (5)
C190.23709 (13)0.3863 (2)0.78079 (13)0.0248 (6)
C200.20370 (13)0.4271 (3)0.70361 (13)0.0265 (6)
C210.23737 (17)0.5511 (3)0.58440 (15)0.0385 (8)
C220.2134 (3)0.4093 (4)0.53244 (19)0.0674 (13)
H20.512000.510800.945400.0290*
H30.550400.314001.038500.0330*
H40.546500.388001.165300.0330*
H50.500700.658901.204700.0280*
H70.421601.080801.017400.0240*
H8A0.432701.136901.159000.0290*
H8B0.476200.994301.206500.0290*
H9A0.360700.829501.213400.0280*
H9B0.352801.013001.253200.0280*
H10A0.220101.005001.236000.0300*
H10B0.223700.824901.192700.0300*
H11A0.114900.980301.155200.0540*
H11B0.170200.957201.085900.0540*
H11C0.166701.136901.128800.0540*
H130.284401.042900.925800.0270*
H140.153601.071200.948700.0290*
H150.068900.852800.913900.0290*
H160.109700.600900.853400.0270*
H180.380000.533100.798700.0230*
H19A0.197800.332900.812100.0300*
H19B0.278600.302500.775200.0300*
H20A0.182200.321600.681400.0320*
H20B0.163100.513500.708300.0320*
H21A0.278500.616900.560700.0460*
H21B0.194500.630500.591400.0460*
H22A0.197000.459300.485200.1010*
H22B0.171700.345000.554600.1010*
H22C0.255800.331600.523700.1010*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0154 (1)0.0183 (1)0.0155 (1)0.0002 (1)0.0009 (1)0.0005 (1)
Cl10.0201 (2)0.0234 (2)0.0193 (2)0.0037 (2)0.0029 (2)0.0018 (2)
Cl20.0224 (2)0.0191 (2)0.0324 (3)0.0009 (2)0.0032 (2)0.0045 (2)
O10.0239 (7)0.0249 (7)0.0215 (7)0.0001 (6)0.0019 (6)0.0017 (6)
O20.0332 (8)0.0377 (9)0.0278 (8)0.0064 (7)0.0009 (7)0.0026 (7)
N10.0193 (8)0.0192 (7)0.0184 (8)0.0010 (6)0.0009 (6)0.0006 (6)
N20.0219 (8)0.0219 (7)0.0183 (9)0.0009 (6)0.0003 (6)0.0044 (7)
N30.0175 (7)0.0202 (7)0.0179 (9)0.0009 (6)0.0009 (6)0.0007 (6)
N40.0183 (7)0.0186 (7)0.0250 (8)0.0011 (6)0.0019 (7)0.0003 (7)
C10.0192 (9)0.0210 (9)0.0152 (8)0.0006 (7)0.0004 (7)0.0006 (7)
C20.0287 (10)0.0232 (9)0.0195 (9)0.0025 (8)0.0022 (8)0.0028 (8)
C30.0365 (11)0.0237 (10)0.0221 (10)0.0048 (9)0.0025 (9)0.0002 (8)
C40.0359 (11)0.0256 (10)0.0199 (10)0.0036 (9)0.0001 (8)0.0054 (8)
C50.0250 (10)0.0306 (10)0.0150 (9)0.0006 (8)0.0012 (8)0.0007 (8)
C60.0203 (9)0.0197 (8)0.0195 (9)0.0009 (7)0.0009 (8)0.0014 (7)
C70.0207 (9)0.0217 (9)0.0176 (9)0.0002 (7)0.0024 (7)0.0015 (7)
C80.0268 (10)0.0257 (10)0.0196 (9)0.0006 (8)0.0001 (8)0.0064 (8)
C90.0280 (10)0.0232 (9)0.0180 (9)0.0025 (8)0.0019 (8)0.0014 (7)
C100.0257 (10)0.0240 (9)0.0244 (10)0.0013 (8)0.0054 (8)0.0001 (8)
C110.0281 (10)0.0464 (14)0.0343 (12)0.0004 (10)0.0023 (10)0.0028 (11)
C120.0146 (8)0.0230 (8)0.0163 (8)0.0010 (6)0.0004 (7)0.0017 (7)
C130.0229 (9)0.0244 (9)0.0199 (9)0.0002 (7)0.0004 (7)0.0021 (8)
C140.0237 (9)0.0279 (10)0.0200 (9)0.0039 (8)0.0014 (8)0.0006 (8)
C150.0177 (9)0.0323 (10)0.0214 (10)0.0046 (8)0.0011 (8)0.0048 (8)
C160.0179 (8)0.0263 (8)0.0236 (9)0.0036 (6)0.0014 (8)0.0038 (9)
C170.0190 (9)0.0209 (8)0.0199 (10)0.0009 (6)0.0012 (7)0.0018 (7)
C180.0169 (8)0.0203 (8)0.0215 (9)0.0003 (7)0.0004 (7)0.0010 (7)
C190.0249 (10)0.0179 (9)0.0315 (11)0.0029 (7)0.0038 (9)0.0017 (8)
C200.0247 (10)0.0239 (10)0.0308 (11)0.0024 (8)0.0026 (8)0.0046 (9)
C210.0492 (15)0.0355 (12)0.0308 (12)0.0024 (11)0.0005 (11)0.0014 (10)
C220.121 (3)0.0460 (17)0.0351 (15)0.0178 (19)0.0190 (18)0.0014 (13)
Geometric parameters (Å, º) top
Ni1—Cl12.2316 (16)C16—C171.397 (3)
Ni1—Cl22.2435 (16)C19—C201.515 (3)
Ni1—N11.981 (2)C21—C221.478 (4)
Ni1—N31.974 (2)C2—H20.9300
O1—C91.418 (3)C3—H30.9300
O1—C101.432 (3)C4—H40.9300
O2—C201.410 (3)C5—H50.9300
O2—C211.433 (3)C7—H70.9300
N1—C11.397 (3)C8—H8A0.9700
N1—C71.325 (3)C8—H8B0.9700
N2—C61.391 (3)C9—H9A0.9700
N2—C71.341 (3)C9—H9B0.9700
N2—C81.456 (3)C10—H10A0.9700
N3—C121.394 (3)C10—H10B0.9700
N3—C181.312 (2)C11—H11A0.9600
N4—C171.389 (3)C11—H11B0.9600
N4—C181.344 (3)C11—H11C0.9600
N4—C191.462 (3)C13—H130.9300
C1—C21.396 (3)C14—H140.9300
C1—C61.401 (3)C15—H150.9300
C2—C31.385 (3)C16—H160.9300
C3—C41.406 (3)C18—H180.9300
C4—C51.377 (3)C19—H19A0.9700
C5—C61.389 (3)C19—H19B0.9700
C8—C91.509 (3)C20—H20A0.9700
C10—C111.498 (4)C20—H20B0.9700
C12—C131.399 (3)C21—H21A0.9700
C12—C171.398 (3)C21—H21B0.9700
C13—C141.383 (3)C22—H22A0.9600
C14—C151.404 (3)C22—H22B0.9600
C15—C161.371 (3)C22—H22C0.9600
Cl1—Ni1—Cl2129.75 (2)C6—C5—H5122.00
Cl1—Ni1—N1107.99 (5)N1—C7—H7123.00
Cl1—Ni1—N3102.59 (5)N2—C7—H7124.00
Cl2—Ni1—N1105.72 (5)N2—C8—H8A109.00
Cl2—Ni1—N3106.66 (5)N2—C8—H8B109.00
N1—Ni1—N3100.48 (7)C9—C8—H8A109.00
C9—O1—C10111.17 (16)C9—C8—H8B109.00
C20—O2—C21113.82 (19)H8A—C8—H8B108.00
Ni1—N1—C1129.27 (13)O1—C9—H9A110.00
Ni1—N1—C7125.20 (14)O1—C9—H9B110.00
C1—N1—C7105.47 (17)C8—C9—H9A110.00
C6—N2—C7107.29 (17)C8—C9—H9B110.00
C6—N2—C8125.60 (17)H9A—C9—H9B108.00
C7—N2—C8127.00 (17)O1—C10—H10A110.00
Ni1—N3—C12127.30 (12)O1—C10—H10B110.00
Ni1—N3—C18126.50 (13)C11—C10—H10A110.00
C12—N3—C18106.21 (15)C11—C10—H10B110.00
C17—N4—C18107.15 (15)H10A—C10—H10B108.00
C17—N4—C19126.84 (16)C10—C11—H11A109.00
C18—N4—C19125.80 (16)C10—C11—H11B109.00
N1—C1—C2130.97 (18)C10—C11—H11C110.00
N1—C1—C6108.73 (16)H11A—C11—H11B109.00
C2—C1—C6120.30 (18)H11A—C11—H11C109.00
C1—C2—C3116.92 (19)H11B—C11—H11C109.00
C2—C3—C4121.8 (2)C12—C13—H13121.00
C3—C4—C5121.7 (2)C14—C13—H13121.00
C4—C5—C6116.23 (19)C13—C14—H14119.00
N2—C6—C1105.54 (17)C15—C14—H14119.00
N2—C6—C5131.49 (19)C14—C15—H15119.00
C1—C6—C5123.0 (2)C16—C15—H15119.00
N1—C7—N2112.97 (19)C15—C16—H16122.00
N2—C8—C9112.19 (18)C17—C16—H16122.00
O1—C9—C8109.12 (16)N3—C18—H18124.00
O1—C10—C11108.96 (18)N4—C18—H18124.00
N3—C12—C13131.16 (16)N4—C19—H19A109.00
N3—C12—C17108.25 (15)N4—C19—H19B109.00
C13—C12—C17120.57 (17)C20—C19—H19A109.00
C12—C13—C14117.23 (19)C20—C19—H19B109.00
C13—C14—C15121.2 (2)H19A—C19—H19B108.00
C14—C15—C16122.57 (19)O2—C20—H20A110.00
C15—C16—C17116.13 (17)O2—C20—H20B110.00
N4—C17—C12105.70 (16)C19—C20—H20A110.00
N4—C17—C16131.94 (16)C19—C20—H20B110.00
C12—C17—C16122.35 (16)H20A—C20—H20B108.00
N3—C18—N4112.69 (16)O2—C21—H21A109.00
N4—C19—C20111.98 (15)O2—C21—H21B109.00
O2—C20—C19108.33 (18)C22—C21—H21A109.00
O2—C21—C22114.7 (2)C22—C21—H21B109.00
C1—C2—H2121.00H21A—C21—H21B108.00
C3—C2—H2122.00C21—C22—H22A109.00
C2—C3—H3119.00C21—C22—H22B110.00
C4—C3—H3119.00C21—C22—H22C110.00
C3—C4—H4119.00H22A—C22—H22B109.00
C5—C4—H4119.00H22A—C22—H22C110.00
C4—C5—H5122.00H22B—C22—H22C109.00
Cl1—Ni1—N1—C129.16 (18)Ni1—N3—C12—C132.4 (3)
Cl2—Ni1—N1—C1171.33 (15)C12—N3—C18—N40.3 (2)
N3—Ni1—N1—C177.88 (17)C17—N4—C19—C2076.7 (3)
Cl1—Ni1—N1—C7154.30 (15)C19—N4—C17—C163.8 (3)
Cl2—Ni1—N1—C712.14 (18)C18—N4—C19—C2097.3 (2)
N3—Ni1—N1—C798.66 (17)C18—N4—C17—C16178.7 (2)
Cl1—Ni1—N3—C12178.37 (15)C17—N4—C18—N30.3 (2)
Cl2—Ni1—N3—C1239.72 (17)C19—N4—C17—C12175.01 (18)
N1—Ni1—N3—C1270.34 (16)C19—N4—C18—N3175.23 (18)
Cl1—Ni1—N3—C182.17 (17)C18—N4—C17—C120.1 (2)
Cl2—Ni1—N3—C18140.82 (15)N1—C1—C2—C3178.8 (2)
N1—Ni1—N3—C18109.12 (17)N1—C1—C6—N20.5 (2)
C10—O1—C9—C8178.56 (17)C6—C1—C2—C30.8 (3)
C9—O1—C10—C11176.14 (19)N1—C1—C6—C5178.96 (19)
C21—O2—C20—C19174.78 (17)C2—C1—C6—N2179.82 (18)
C20—O2—C21—C2270.7 (3)C2—C1—C6—C50.8 (3)
Ni1—N1—C1—C6177.71 (14)C1—C2—C3—C40.0 (3)
C1—N1—C7—N20.6 (2)C2—C3—C4—C51.0 (4)
C7—N1—C1—C2179.7 (2)C3—C4—C5—C61.1 (3)
C7—N1—C1—C60.7 (2)C4—C5—C6—N2179.1 (2)
Ni1—N1—C7—N2177.83 (13)C4—C5—C6—C10.2 (3)
Ni1—N1—C1—C22.6 (3)N2—C8—C9—O165.2 (2)
C6—N2—C7—N10.3 (2)N3—C12—C13—C14178.4 (2)
C7—N2—C6—C10.1 (2)C13—C12—C17—N4178.43 (18)
C7—N2—C8—C998.4 (2)C13—C12—C17—C160.5 (3)
C7—N2—C6—C5179.3 (2)C17—C12—C13—C140.3 (3)
C8—N2—C6—C1176.18 (18)N3—C12—C17—C16178.97 (18)
C6—N2—C8—C977.2 (2)N3—C12—C17—N40.0 (2)
C8—N2—C7—N1176.54 (18)C12—C13—C14—C150.3 (3)
C8—N2—C6—C54.5 (3)C13—C14—C15—C160.7 (3)
C18—N3—C12—C13178.1 (2)C14—C15—C16—C170.4 (3)
Ni1—N3—C12—C17179.34 (13)C15—C16—C17—C120.1 (3)
C18—N3—C12—C170.2 (2)C15—C16—C17—N4178.5 (2)
Ni1—N3—C18—N4179.24 (13)N4—C19—C20—O263.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···Cl10.932.803.514 (3)134
C15—H15···Cl2i0.932.823.612 (3)143
C16—H16···Cl1ii0.932.783.699 (3)169
C20—H20A···O1iii0.972.523.372 (3)146
Symmetry codes: (i) x1/2, y+2, z; (ii) x1/2, y+1, z; (iii) x+1/2, y1, z1/2.
 

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