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The Cu centre in the title compound, [CuCl(C9H11N3)2]NO3, is coordinated by a cyclic imino N atom and exocyclic amino N atoms derived from two 2-amino­ethyl­benzimidazole ligands, as well as a Cl atom; the Cu and Cl atoms lie on a twofold axis. The coordination geometry is based on a trigonal bipyramid.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046897/tk2095sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046897/tk2095Isup2.hkl
Contains datablock I

CCDC reference: 630489

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in solvent or counterion
  • R factor = 0.038
  • wR factor = 0.106
  • Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ... 2072.00 Ang-3 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N4 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 43.00 Perc. PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.43 Ratio
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL022_ALERT_1_A There is a mismatched ~ on line 111 The Cu centre in the title compound, [CuCl(C~9~H~11~N~3)~2~]NO~3~, is If you require a ~ then it should be escaped with a \, i.e. \~ Otherwise there must be a matching closing ~, e.g. C~2~H~4~
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: SMART-NT (Bruker, 1998); cell refinement: SMART-NT; data reduction: SAINT-NT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); 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)chlorocopper(II) nitrate top
Crystal data top
[CuCl(C9H11N3)2]NO3F(000) = 996
Mr = 483.42Dx = 1.549 Mg m3
Orthorhombic, PccnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2acCell parameters from 803 reflections
a = 11.251 (10) Åθ = 2.7–24.3°
b = 14.860 (14) ŵ = 1.22 mm1
c = 12.396 (12) ÅT = 293 K
V = 2072 (3) Å3Block, blue
Z = 40.22 × 0.18 × 0.14 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1320 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.054
Graphite monochromatorθmax = 26.4°, θmin = 2.3°
φ and ω scansh = 1411
11006 measured reflectionsk = 1718
2124 independent reflectionsl = 1315
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0504P)2 + 0.8135P]
where P = (Fo2 + 2Fc2)/3
2124 reflections(Δ/σ)max < 0.001
151 parametersΔρmax = 0.49 e Å3
25 restraintsΔρmin = 0.53 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*/UeqOcc. (<1)
Cu10.25000.25000.42602 (5)0.02840 (19)
Cl10.25000.25000.22890 (10)0.0476 (4)
N10.3196 (2)0.12649 (17)0.4258 (2)0.0322 (6)
N20.3337 (3)0.02018 (19)0.4453 (3)0.0477 (9)
H2A0.31670.07400.46580.057*
N30.0970 (2)0.20541 (17)0.5050 (2)0.0343 (7)
H3A0.10290.22250.57450.041*
H3B0.03500.23550.47660.041*
C10.4185 (3)0.0959 (2)0.3665 (3)0.0384 (9)
C20.5020 (4)0.1414 (3)0.3063 (3)0.0522 (11)
H20.49770.20340.29670.063*
C30.5927 (4)0.0910 (4)0.2604 (4)0.0670 (14)
H30.65140.12040.22090.080*
C40.5984 (5)0.0013 (4)0.2715 (4)0.0737 (16)
H40.65960.03280.23790.088*
C50.5169 (4)0.0470 (3)0.3302 (4)0.0646 (14)
H50.52070.10920.33750.078*
C60.4267 (4)0.0031 (3)0.3793 (3)0.0460 (10)
C70.2736 (3)0.0544 (2)0.4728 (3)0.0353 (9)
C80.1703 (3)0.0545 (2)0.5461 (3)0.0428 (9)
H8A0.19470.07850.61550.051*
H8B0.14450.00710.55740.051*
C90.0663 (3)0.1092 (2)0.5044 (3)0.0380 (8)
H9A0.04690.09040.43150.046*
H9B0.00280.09900.54950.046*
N40.25000.75000.4948 (5)0.088 (2)
O10.2090 (7)0.8238 (4)0.5335 (7)0.084 (2)0.50
O20.3406 (8)0.7245 (9)0.4765 (10)0.180 (6)0.50
O30.1514 (6)0.7005 (4)0.4762 (7)0.090 (2)0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0256 (3)0.0248 (3)0.0348 (3)0.0025 (3)0.0000.000
Cl10.0582 (9)0.0552 (8)0.0293 (7)0.0214 (7)0.0000.000
N10.0293 (15)0.0309 (15)0.0364 (16)0.0040 (12)0.0026 (13)0.0016 (13)
N20.057 (2)0.0260 (15)0.060 (2)0.0062 (14)0.0175 (18)0.0054 (15)
N30.0293 (15)0.0344 (15)0.0392 (16)0.0009 (13)0.0018 (14)0.0004 (14)
C10.036 (2)0.046 (2)0.0331 (19)0.0158 (17)0.0091 (17)0.0083 (17)
C20.042 (2)0.071 (3)0.044 (2)0.014 (2)0.005 (2)0.002 (2)
C30.045 (3)0.114 (4)0.042 (3)0.026 (3)0.001 (2)0.001 (3)
C40.064 (3)0.116 (5)0.041 (3)0.049 (3)0.010 (2)0.022 (3)
C50.075 (3)0.067 (3)0.051 (3)0.041 (3)0.025 (3)0.025 (3)
C60.050 (2)0.048 (2)0.040 (2)0.0182 (19)0.016 (2)0.015 (2)
C70.041 (2)0.0260 (16)0.039 (2)0.0010 (15)0.0126 (16)0.0044 (15)
C80.044 (2)0.0339 (18)0.051 (2)0.0099 (18)0.0070 (18)0.0089 (18)
C90.0326 (19)0.038 (2)0.043 (2)0.0114 (15)0.0015 (17)0.0015 (17)
N40.141 (7)0.037 (3)0.087 (5)0.013 (5)0.0000.000
O10.083 (5)0.049 (4)0.120 (6)0.008 (4)0.002 (4)0.012 (4)
O20.131 (9)0.214 (11)0.195 (10)0.043 (8)0.006 (8)0.059 (9)
O30.079 (5)0.040 (4)0.151 (7)0.013 (4)0.008 (4)0.021 (4)
Geometric parameters (Å, º) top
Cu1—Cl12.444 (3)C5—C61.398 (6)
Cu1—N1i1.995 (3)C5—H50.9300
Cu1—N11.995 (3)C7—C81.475 (5)
Cu1—N3i2.088 (3)C8—C91.517 (5)
Cu1—N32.088 (3)C8—H8A0.9700
N1—C71.324 (4)C8—H8B0.9700
N1—C11.410 (4)C9—H9A0.9700
N2—C71.343 (4)C9—H9B0.9700
N2—C61.372 (5)N4—O2ii1.112 (7)
N2—H2A0.8600N4—O21.112 (7)
N3—C91.471 (4)N4—O11.283 (6)
N3—H3A0.9000N4—O1ii1.283 (6)
N3—H3B0.9000N4—O31.350 (6)
C1—C21.377 (6)N4—O3ii1.350 (6)
C1—C61.391 (5)O1—O2ii1.152 (14)
C2—C31.387 (6)O1—O3ii1.761 (10)
C2—H20.9300O2—O3ii1.118 (14)
C3—C41.381 (7)O2—O1ii1.152 (14)
C3—H30.9300O3—O2ii1.118 (14)
C4—C51.354 (7)O3—O1ii1.761 (10)
C4—H40.9300
Cl1i—Cu1—N189.94 (8)N1—C7—N2111.0 (3)
Cl1i—Cu1—N3117.97 (9)N1—C7—C8125.4 (3)
N1i—Cu1—N3i91.84 (12)N2—C7—C8123.6 (3)
N1i—Cu1—N1179.87 (16)C7—C8—C9113.4 (3)
N1—Cu1—N3i88.22 (11)C7—C8—H8A108.9
N1i—Cu1—N388.22 (12)C9—C8—H8A108.9
N1—Cu1—N391.84 (12)C7—C8—H8B108.9
N3i—Cu1—N3124.05 (18)C9—C8—H8B108.9
N1—Cu1—Cl189.94 (8)H8A—C8—H8B107.7
N3—Cu1—Cl1117.97 (9)N3—C9—C8109.7 (3)
C7—N1—C1106.1 (3)N3—C9—H9A109.7
C7—N1—Cu1126.1 (2)C8—C9—H9A109.7
C1—N1—Cu1127.4 (2)N3—C9—H9B109.7
C7—N2—C6109.1 (3)C8—C9—H9B109.7
C7—N2—H2A125.4H9A—C9—H9B108.2
C6—N2—H2A125.4O2ii—N4—O2156.4 (11)
C9—N3—Cu1120.0 (2)O2ii—N4—O157.0 (7)
C9—N3—H3A107.3O2—N4—O1134.3 (7)
Cu1—N3—H3A107.3O2ii—N4—O1ii134.3 (7)
C9—N3—H3B107.3O2—N4—O1ii57.0 (7)
Cu1—N3—H3B107.3O1—N4—O1ii136.2 (8)
H3A—N3—H3B106.9O2ii—N4—O352.9 (7)
C2—C1—C6120.2 (4)O2—N4—O3122.2 (7)
C2—C1—N1131.5 (4)O1—N4—O3103.5 (4)
C6—C1—N1108.2 (3)O1ii—N4—O383.9 (4)
C1—C2—C3117.3 (4)O2ii—N4—O3ii122.2 (7)
C1—C2—H2121.3O2—N4—O3ii52.9 (7)
C3—C2—H2121.3O1—N4—O3ii83.9 (4)
C4—C3—C2122.0 (5)O1ii—N4—O3ii103.5 (4)
C4—C3—H3119.0O3—N4—O3ii160.3 (8)
C2—C3—H3119.0O2ii—O1—N454.0 (5)
C5—C4—C3121.4 (4)O2ii—O1—O3ii93.3 (7)
C5—C4—H4119.3N4—O1—O3ii49.7 (3)
C3—C4—H4119.3N4—O2—O3ii74.6 (6)
C4—C5—C6117.3 (5)N4—O2—O1ii69.0 (6)
C4—C5—H5121.3O3ii—O2—O1ii131.5 (12)
C6—C5—H5121.3O2ii—O3—N452.5 (5)
N2—C6—C1105.5 (3)O2ii—O3—O1ii97.6 (7)
N2—C6—C5132.8 (4)N4—O3—O1ii46.4 (3)
C1—C6—C5121.7 (4)
N3i—Cu1—N1—C7119.0 (3)C6—N2—C7—N11.8 (4)
N3—Cu1—N1—C75.0 (3)C6—N2—C7—C8177.9 (3)
Cl1—Cu1—N1—C7123.0 (3)N1—C7—C8—C946.9 (5)
N3i—Cu1—N1—C169.0 (3)N2—C7—C8—C9133.4 (3)
N3—Cu1—N1—C1167.0 (3)Cu1—N3—C9—C854.4 (4)
Cl1—Cu1—N1—C149.0 (3)C7—C8—C9—N368.6 (4)
N1i—Cu1—N3—C9160.7 (3)O2—N4—O1—O2ii153.2 (12)
N1—Cu1—N3—C919.2 (3)O1ii—N4—O1—O2ii121.7 (9)
N3i—Cu1—N3—C9108.3 (3)O3—N4—O1—O2ii26.3 (10)
Cl1—Cu1—N3—C971.7 (3)O3ii—N4—O1—O2ii135.1 (9)
C7—N1—C1—C2176.9 (4)O2ii—N4—O1—O3ii135.1 (9)
Cu1—N1—C1—C29.8 (6)O2—N4—O1—O3ii18.0 (9)
C7—N1—C1—C61.1 (4)O1ii—N4—O1—O3ii103.2 (4)
Cu1—N1—C1—C6172.2 (2)O3—N4—O1—O3ii161.5 (8)
C6—C1—C2—C30.2 (6)O2ii—N4—O2—O3ii86.5 (8)
N1—C1—C2—C3177.5 (4)O1—N4—O2—O3ii22.7 (11)
C1—C2—C3—C41.7 (6)O1ii—N4—O2—O3ii147.3 (13)
C2—C3—C4—C51.6 (7)O3—N4—O2—O3ii156.7 (10)
C3—C4—C5—C60.2 (6)O2ii—N4—O2—O1ii126.2 (8)
C7—N2—C6—C11.1 (4)O1—N4—O2—O1ii124.6 (10)
C7—N2—C6—C5178.6 (4)O3—N4—O2—O1ii56.0 (9)
C2—C1—C6—N2178.2 (3)O3ii—N4—O2—O1ii147.3 (13)
N1—C1—C6—N20.0 (4)O2—N4—O3—O2ii151.8 (13)
C2—C1—C6—C51.6 (6)O1—N4—O3—O2ii27.8 (12)
N1—C1—C6—C5179.7 (3)O1ii—N4—O3—O2ii163.9 (8)
C4—C5—C6—N2178.0 (4)O3ii—N4—O3—O2ii82.6 (8)
C4—C5—C6—C11.7 (6)O2ii—N4—O3—O1ii163.9 (8)
C1—N1—C7—N21.8 (4)O2—N4—O3—O1ii44.3 (8)
Cu1—N1—C7—N2171.6 (2)O1—N4—O3—O1ii136.1 (8)
C1—N1—C7—C8178.0 (3)O3ii—N4—O3—O1ii113.5 (4)
Cu1—N1—C7—C88.6 (5)
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x+1/2, y+3/2, z.
 

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