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The title compound, [CuCl(C9H11N3)]ClO4, was prepared by reaction of 2-amino­ethyl­benz­imidazole di­hydro­chloride with copper(II) perchlorate. The crystal structure is built of bis(2-amino­ethyl­benz­imidazole)­chloro­copper(II) cations and perchlorate anions. Both cation and anion occupy special positions on a twofold axis. Each of the amino­ethyl­benz­imidazole ligands coordinates the Cu atom through one cyclic imine and one exocyclic amine group. The chloro ligand occupies the fifth coordination site in the Cu-atom environment, thus forming a trigonal bipyramid, with the Cl atom and amine N atoms in the equatorial and both cyclic imine atoms in the axial positions [the N—Cu—N angle formed by the axial bonds is 179.61 (10)°]. N—H...Cl and N—H...O hydrogen-bonding interactions link cations and anions into layers normal to the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804016332/ya6212sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804016332/ya6212Isup2.hkl
Contains datablock I

CCDC reference: 248732

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.030
  • wR factor = 0.079
  • Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.665 0.807 Tmin' and Tmax expected: 0.760 0.807 RR' = 0.875 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.87 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - Cl1 .. 9.83 su PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... Cl2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Bis(2-aminoethyl-1H-benzimidazole-κN3)chlorocopper(II) perchlorate top
Crystal data top
[CuCl(C9H11N3)]ClO4Dx = 1.650 Mg m3
Mr = 520.86Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PccnCell parameters from 788 reflections
a = 15.202 (5) Åθ = 2.2–26.2°
b = 11.241 (4) ŵ = 1.34 mm1
c = 12.268 (4) ÅT = 293 K
V = 2096.4 (11) Å3Block, blue
Z = 40.20 × 0.18 × 0.16 mm
F(000) = 1068
Data collection top
Bruker SMART CCD area-detector
diffractometer
2145 independent reflections
Radiation source: fine-focus sealed tube1541 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
φ and ω scansθmax = 26.4°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1818
Tmin = 0.665, Tmax = 0.807k = 145
11264 measured reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0359P)2 + 1.0483P]
where P = (Fo2 + 2Fc2)/3
2145 reflections(Δ/σ)max < 0.001
142 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.31 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Cu10.25000.25000.07034 (3)0.02575 (12)
Cl10.25000.25000.26978 (7)0.0517 (3)
N10.29424 (12)0.09617 (16)0.00636 (16)0.0314 (4)
H1A0.26460.03470.02300.038*
H1B0.27770.10090.07670.038*
N20.37172 (12)0.31972 (16)0.07089 (15)0.0269 (4)
N30.51614 (12)0.33012 (19)0.05370 (16)0.0343 (5)
H30.56870.31170.03390.041*
C10.38826 (15)0.0642 (2)0.0051 (2)0.0328 (5)
H1C0.39780.00580.04990.039*
H1D0.40640.04570.06880.039*
C20.44262 (15)0.1671 (2)0.0487 (2)0.0342 (5)
H2A0.50280.14060.05900.041*
H2B0.41970.19060.11920.041*
C30.44241 (14)0.2719 (2)0.02483 (18)0.0290 (5)
C40.49349 (15)0.4241 (2)0.1202 (2)0.0337 (5)
C50.54314 (19)0.5131 (3)0.1700 (2)0.0443 (7)
H50.60410.51520.16420.053*
C60.4979 (2)0.5973 (3)0.2280 (2)0.0487 (7)
H60.52900.65820.26180.058*
C70.4064 (2)0.5941 (2)0.2376 (2)0.0446 (7)
H70.37790.65380.27650.054*
C80.35726 (18)0.5041 (2)0.19061 (19)0.0379 (6)
H80.29650.50110.19870.046*
C90.40216 (15)0.4182 (2)0.13085 (19)0.0290 (5)
Cl20.75000.25000.00154 (11)0.0563 (3)
O10.71043 (16)0.3398 (2)0.0672 (2)0.0884 (9)
O20.68326 (15)0.1965 (2)0.0632 (2)0.0842 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.01982 (19)0.0241 (2)0.0334 (2)0.00098 (17)0.0000.000
Cl10.0629 (6)0.0647 (6)0.0275 (5)0.0310 (6)0.0000.000
N10.0294 (10)0.0278 (10)0.0369 (11)0.0020 (9)0.0008 (9)0.0029 (10)
N20.0236 (9)0.0251 (10)0.0321 (10)0.0011 (8)0.0003 (8)0.0006 (9)
N30.0197 (10)0.0402 (12)0.0429 (12)0.0027 (9)0.0005 (9)0.0061 (10)
C10.0358 (13)0.0265 (12)0.0362 (13)0.0063 (10)0.0006 (11)0.0020 (11)
C20.0263 (12)0.0364 (13)0.0400 (13)0.0060 (11)0.0038 (11)0.0016 (11)
C30.0213 (10)0.0311 (13)0.0347 (13)0.0009 (9)0.0000 (9)0.0079 (10)
C40.0330 (12)0.0366 (14)0.0314 (12)0.0081 (10)0.0054 (11)0.0073 (12)
C50.0416 (15)0.0506 (17)0.0408 (15)0.0208 (13)0.0111 (12)0.0103 (14)
C60.070 (2)0.0441 (17)0.0324 (15)0.0244 (16)0.0106 (14)0.0018 (13)
C70.0695 (19)0.0348 (14)0.0295 (14)0.0058 (14)0.0008 (13)0.0012 (12)
C80.0446 (15)0.0341 (14)0.0352 (13)0.0039 (11)0.0002 (12)0.0016 (12)
C90.0314 (12)0.0277 (12)0.0278 (12)0.0065 (10)0.0030 (10)0.0049 (11)
Cl20.0238 (4)0.0328 (5)0.1124 (9)0.0021 (4)0.0000.000
O10.0532 (14)0.0585 (14)0.154 (3)0.0077 (12)0.0329 (15)0.0158 (16)
O20.0517 (14)0.0651 (14)0.136 (2)0.0195 (13)0.0338 (14)0.0100 (15)
Geometric parameters (Å, º) top
Cu1—N12.0803 (19)C2—H2B0.9700
Cu1—N22.0095 (18)C4—C51.395 (3)
Cu1—Cl12.4468 (12)C4—C91.396 (3)
N1—C11.474 (3)C5—C61.368 (4)
N1—H1A0.9000C5—H50.9300
N1—H1B0.9000C6—C71.397 (4)
N2—C31.328 (3)C6—H60.9300
N2—C91.407 (3)C7—C81.383 (4)
N3—C31.345 (3)C7—H70.9300
N3—C41.378 (3)C8—C91.392 (3)
N3—H30.8600C8—H80.9300
C1—C21.518 (3)Cl2—O21.422 (2)
C1—H1C0.9700Cl2—O2i1.422 (2)
C1—H1D0.9700Cl2—O1i1.425 (2)
C2—C31.484 (3)Cl2—O11.425 (2)
C2—H2A0.9700
N2—Cu1—N2ii179.61 (10)H2A—C2—H2B107.8
N2—Cu1—N1ii88.57 (7)N2—C3—N3111.4 (2)
N2—Cu1—N191.60 (7)N2—C3—C2125.6 (2)
N1ii—Cu1—N1126.22 (11)N3—C3—C2123.0 (2)
N2—Cu1—Cl189.81 (5)N3—C4—C5132.4 (2)
N1—Cu1—Cl1116.89 (6)N3—C4—C9105.5 (2)
C1—N1—Cu1120.76 (14)C5—C4—C9122.1 (3)
C1—N1—H1A107.1C6—C5—C4116.9 (3)
Cu1—N1—H1A107.1C6—C5—H5121.6
C1—N1—H1B107.1C4—C5—H5121.6
Cu1—N1—H1B107.1C5—C6—C7121.8 (3)
H1A—N1—H1B106.8C5—C6—H6119.1
C3—N2—C9105.94 (18)C7—C6—H6119.1
C3—N2—Cu1125.87 (15)C8—C7—C6121.4 (3)
C9—N2—Cu1127.69 (15)C8—C7—H7119.3
C3—N3—C4108.67 (19)C6—C7—H7119.3
C3—N3—H3125.7C7—C8—C9117.5 (3)
C4—N3—H3125.7C7—C8—H8121.2
N1—C1—C2109.80 (18)C9—C8—H8121.2
N1—C1—H1C109.7C8—C9—C4120.3 (2)
C2—C1—H1C109.7C8—C9—N2131.3 (2)
N1—C1—H1D109.7C4—C9—N2108.4 (2)
C2—C1—H1D109.7O2—Cl2—O2i112.1 (2)
H1C—C1—H1D108.2O2—Cl2—O1i108.48 (14)
C3—C2—C1112.9 (2)O2i—Cl2—O1i108.32 (16)
C3—C2—H2A109.0O2—Cl2—O1108.32 (16)
C1—C2—H2A109.0O2i—Cl2—O1108.48 (14)
C3—C2—H2B109.0O1i—Cl2—O1111.1 (2)
C1—C2—H2B109.0
N2—Cu1—N1—C118.96 (17)C1—C2—C3—N3132.2 (2)
N2ii—Cu1—N1—C1160.69 (17)C3—N3—C4—C5178.2 (3)
N1ii—Cu1—N1—C1108.37 (17)C3—N3—C4—C90.8 (3)
Cl1—Cu1—N1—C171.63 (17)N3—C4—C5—C6177.1 (3)
N1ii—Cu1—N2—C3121.24 (19)C9—C4—C5—C61.8 (4)
N1—Cu1—N2—C34.96 (18)C4—C5—C6—C70.4 (4)
Cl1—Cu1—N2—C3121.85 (18)C5—C6—C7—C81.3 (4)
N1ii—Cu1—N2—C968.06 (18)C6—C7—C8—C91.6 (4)
N1—Cu1—N2—C9165.75 (18)C7—C8—C9—C40.3 (3)
Cl1—Cu1—N2—C948.85 (17)C7—C8—C9—N2177.4 (2)
Cu1—N1—C1—C254.4 (2)N3—C4—C9—C8177.7 (2)
N1—C1—C2—C368.2 (3)C5—C4—C9—C81.4 (4)
C9—N2—C3—N32.0 (2)N3—C4—C9—N20.5 (3)
Cu1—N2—C3—N3170.35 (15)C5—C4—C9—N2179.6 (2)
C9—N2—C3—C2178.5 (2)C3—N2—C9—C8176.4 (2)
Cu1—N2—C3—C29.1 (3)Cu1—N2—C9—C811.5 (4)
C4—N3—C3—N21.8 (3)C3—N2—C9—C41.5 (2)
C4—N3—C3—C2178.7 (2)Cu1—N2—C9—C4170.68 (16)
C1—C2—C3—N247.2 (3)
Symmetry codes: (i) x+3/2, y+1/2, z; (ii) x+1/2, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···Cl1iii0.902.563.314 (2)142
N3—H3···O10.862.222.960 (4)145
Symmetry code: (iii) x, y+1/2, z1/2.
 

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