Bis(2-amino­ethyl-1H-benzimidazole)chloro­copper(II) nitrate

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.

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

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

Crystal data

[CuCl(C9H11N3)2]NO3	F(000) = 996
Mr = 483.42	Dx = 1.549 Mg m^−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 803 reflections
a = 11.251 (10) Å	θ = 2.7–24.3°
b = 14.860 (14) Å	µ = 1.22 mm^−1
c = 12.396 (12) Å	T = 293 K
V = 2072 (3) Å^3	Block, blue
Z = 4	0.22 × 0.18 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1320 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.054
Graphite monochromator	θmax = 26.4°, θmin = 2.3°
φ and ω scans	h = −14→11
11006 measured reflections	k = −17→18
2124 independent reflections	l = −13→15

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.106	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0504P)^2 + 0.8135P] where P = (Fo^2 + 2Fc^2)/3
2124 reflections	(Δ/σ)max < 0.001
151 parameters	Δρmax = 0.49 e Å^−3
25 restraints	Δρmin = −0.53 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)
Cu1	0.2500	0.2500	0.42602 (5)	0.02840 (19)
Cl1	0.2500	0.2500	0.22890 (10)	0.0476 (4)
N1	0.3196 (2)	0.12649 (17)	0.4258 (2)	0.0322 (6)
N2	0.3337 (3)	−0.02018 (19)	0.4453 (3)	0.0477 (9)
H2A	0.3167	−0.0740	0.4658	0.057*
N3	0.0970 (2)	0.20541 (17)	0.5050 (2)	0.0343 (7)
H3A	0.1029	0.2225	0.5745	0.041*
H3B	0.0350	0.2355	0.4766	0.041*
C1	0.4185 (3)	0.0959 (2)	0.3665 (3)	0.0384 (9)
C2	0.5020 (4)	0.1414 (3)	0.3063 (3)	0.0522 (11)
H2	0.4977	0.2034	0.2967	0.063*
C3	0.5927 (4)	0.0910 (4)	0.2604 (4)	0.0670 (14)
H3	0.6514	0.1204	0.2209	0.080*
C4	0.5984 (5)	−0.0013 (4)	0.2715 (4)	0.0737 (16)
H4	0.6596	−0.0328	0.2379	0.088*
C5	0.5169 (4)	−0.0470 (3)	0.3302 (4)	0.0646 (14)
H5	0.5207	−0.1092	0.3375	0.078*
C6	0.4267 (4)	0.0031 (3)	0.3793 (3)	0.0460 (10)
C7	0.2736 (3)	0.0544 (2)	0.4728 (3)	0.0353 (9)
C8	0.1703 (3)	0.0545 (2)	0.5461 (3)	0.0428 (9)
H8A	0.1947	0.0785	0.6155	0.051*
H8B	0.1445	−0.0071	0.5574	0.051*
C9	0.0663 (3)	0.1092 (2)	0.5044 (3)	0.0380 (8)
H9A	0.0469	0.0904	0.4315	0.046*
H9B	−0.0028	0.0990	0.5495	0.046*
N4	0.2500	0.7500	0.4948 (5)	0.088 (2)
O1	0.2090 (7)	0.8238 (4)	0.5335 (7)	0.084 (2)	0.50
O2	0.3406 (8)	0.7245 (9)	0.4765 (10)	0.180 (6)	0.50
O3	0.1514 (6)	0.7005 (4)	0.4762 (7)	0.090 (2)	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0256 (3)	0.0248 (3)	0.0348 (3)	0.0025 (3)	0.000	0.000
Cl1	0.0582 (9)	0.0552 (8)	0.0293 (7)	0.0214 (7)	0.000	0.000
N1	0.0293 (15)	0.0309 (15)	0.0364 (16)	0.0040 (12)	−0.0026 (13)	−0.0016 (13)
N2	0.057 (2)	0.0260 (15)	0.060 (2)	0.0062 (14)	−0.0175 (18)	−0.0054 (15)
N3	0.0293 (15)	0.0344 (15)	0.0392 (16)	−0.0009 (13)	0.0018 (14)	−0.0004 (14)
C1	0.036 (2)	0.046 (2)	0.0331 (19)	0.0158 (17)	−0.0091 (17)	−0.0083 (17)
C2	0.042 (2)	0.071 (3)	0.044 (2)	0.014 (2)	0.005 (2)	0.002 (2)
C3	0.045 (3)	0.114 (4)	0.042 (3)	0.026 (3)	0.001 (2)	−0.001 (3)
C4	0.064 (3)	0.116 (5)	0.041 (3)	0.049 (3)	−0.010 (2)	−0.022 (3)
C5	0.075 (3)	0.067 (3)	0.051 (3)	0.041 (3)	−0.025 (3)	−0.025 (3)
C6	0.050 (2)	0.048 (2)	0.040 (2)	0.0182 (19)	−0.016 (2)	−0.015 (2)
C7	0.041 (2)	0.0260 (16)	0.039 (2)	−0.0010 (15)	−0.0126 (16)	−0.0044 (15)
C8	0.044 (2)	0.0339 (18)	0.051 (2)	−0.0099 (18)	−0.0070 (18)	0.0089 (18)
C9	0.0326 (19)	0.038 (2)	0.043 (2)	−0.0114 (15)	0.0015 (17)	−0.0015 (17)
N4	0.141 (7)	0.037 (3)	0.087 (5)	−0.013 (5)	0.000	0.000
O1	0.083 (5)	0.049 (4)	0.120 (6)	0.008 (4)	−0.002 (4)	−0.012 (4)
O2	0.131 (9)	0.214 (11)	0.195 (10)	0.043 (8)	0.006 (8)	−0.059 (9)
O3	0.079 (5)	0.040 (4)	0.151 (7)	0.013 (4)	0.008 (4)	−0.021 (4)

Geometric parameters (Å, º)

Cu1—Cl1	2.444 (3)	C5—C6	1.398 (6)
Cu1—N1^i	1.995 (3)	C5—H5	0.9300
Cu1—N1	1.995 (3)	C7—C8	1.475 (5)
Cu1—N3^i	2.088 (3)	C8—C9	1.517 (5)
Cu1—N3	2.088 (3)	C8—H8A	0.9700
N1—C7	1.324 (4)	C8—H8B	0.9700
N1—C1	1.410 (4)	C9—H9A	0.9700
N2—C7	1.343 (4)	C9—H9B	0.9700
N2—C6	1.372 (5)	N4—O2^ii	1.112 (7)
N2—H2A	0.8600	N4—O2	1.112 (7)
N3—C9	1.471 (4)	N4—O1	1.283 (6)
N3—H3A	0.9000	N4—O1^ii	1.283 (6)
N3—H3B	0.9000	N4—O3	1.350 (6)
C1—C2	1.377 (6)	N4—O3^ii	1.350 (6)
C1—C6	1.391 (5)	O1—O2^ii	1.152 (14)
C2—C3	1.387 (6)	O1—O3^ii	1.761 (10)
C2—H2	0.9300	O2—O3^ii	1.118 (14)
C3—C4	1.381 (7)	O2—O1^ii	1.152 (14)
C3—H3	0.9300	O3—O2^ii	1.118 (14)
C4—C5	1.354 (7)	O3—O1^ii	1.761 (10)
C4—H4	0.9300
Cl1^i—Cu1—N1	89.94 (8)	N1—C7—N2	111.0 (3)
Cl1^i—Cu1—N3	117.97 (9)	N1—C7—C8	125.4 (3)
N1^i—Cu1—N3^i	91.84 (12)	N2—C7—C8	123.6 (3)
N1^i—Cu1—N1	179.87 (16)	C7—C8—C9	113.4 (3)
N1—Cu1—N3^i	88.22 (11)	C7—C8—H8A	108.9
N1^i—Cu1—N3	88.22 (12)	C9—C8—H8A	108.9
N1—Cu1—N3	91.84 (12)	C7—C8—H8B	108.9
N3^i—Cu1—N3	124.05 (18)	C9—C8—H8B	108.9
N1—Cu1—Cl1	89.94 (8)	H8A—C8—H8B	107.7
N3—Cu1—Cl1	117.97 (9)	N3—C9—C8	109.7 (3)
C7—N1—C1	106.1 (3)	N3—C9—H9A	109.7
C7—N1—Cu1	126.1 (2)	C8—C9—H9A	109.7
C1—N1—Cu1	127.4 (2)	N3—C9—H9B	109.7
C7—N2—C6	109.1 (3)	C8—C9—H9B	109.7
C7—N2—H2A	125.4	H9A—C9—H9B	108.2
C6—N2—H2A	125.4	O2^ii—N4—O2	156.4 (11)
C9—N3—Cu1	120.0 (2)	O2^ii—N4—O1	57.0 (7)
C9—N3—H3A	107.3	O2—N4—O1	134.3 (7)
Cu1—N3—H3A	107.3	O2^ii—N4—O1^ii	134.3 (7)
C9—N3—H3B	107.3	O2—N4—O1^ii	57.0 (7)
Cu1—N3—H3B	107.3	O1—N4—O1^ii	136.2 (8)
H3A—N3—H3B	106.9	O2^ii—N4—O3	52.9 (7)
C2—C1—C6	120.2 (4)	O2—N4—O3	122.2 (7)
C2—C1—N1	131.5 (4)	O1—N4—O3	103.5 (4)
C6—C1—N1	108.2 (3)	O1^ii—N4—O3	83.9 (4)
C1—C2—C3	117.3 (4)	O2^ii—N4—O3^ii	122.2 (7)
C1—C2—H2	121.3	O2—N4—O3^ii	52.9 (7)
C3—C2—H2	121.3	O1—N4—O3^ii	83.9 (4)
C4—C3—C2	122.0 (5)	O1^ii—N4—O3^ii	103.5 (4)
C4—C3—H3	119.0	O3—N4—O3^ii	160.3 (8)
C2—C3—H3	119.0	O2^ii—O1—N4	54.0 (5)
C5—C4—C3	121.4 (4)	O2^ii—O1—O3^ii	93.3 (7)
C5—C4—H4	119.3	N4—O1—O3^ii	49.7 (3)
C3—C4—H4	119.3	N4—O2—O3^ii	74.6 (6)
C4—C5—C6	117.3 (5)	N4—O2—O1^ii	69.0 (6)
C4—C5—H5	121.3	O3^ii—O2—O1^ii	131.5 (12)
C6—C5—H5	121.3	O2^ii—O3—N4	52.5 (5)
N2—C6—C1	105.5 (3)	O2^ii—O3—O1^ii	97.6 (7)
N2—C6—C5	132.8 (4)	N4—O3—O1^ii	46.4 (3)
C1—C6—C5	121.7 (4)
N3^i—Cu1—N1—C7	119.0 (3)	C6—N2—C7—N1	1.8 (4)
N3—Cu1—N1—C7	−5.0 (3)	C6—N2—C7—C8	−177.9 (3)
Cl1—Cu1—N1—C7	−123.0 (3)	N1—C7—C8—C9	46.9 (5)
N3^i—Cu1—N1—C1	−69.0 (3)	N2—C7—C8—C9	−133.4 (3)
N3—Cu1—N1—C1	167.0 (3)	Cu1—N3—C9—C8	54.4 (4)
Cl1—Cu1—N1—C1	49.0 (3)	C7—C8—C9—N3	−68.6 (4)
N1^i—Cu1—N3—C9	160.7 (3)	O2—N4—O1—O2^ii	153.2 (12)
N1—Cu1—N3—C9	−19.2 (3)	O1^ii—N4—O1—O2^ii	−121.7 (9)
N3^i—Cu1—N3—C9	−108.3 (3)	O3—N4—O1—O2^ii	−26.3 (10)
Cl1—Cu1—N3—C9	71.7 (3)	O3^ii—N4—O1—O2^ii	135.1 (9)
C7—N1—C1—C2	−176.9 (4)	O2^ii—N4—O1—O3^ii	−135.1 (9)
Cu1—N1—C1—C2	9.8 (6)	O2—N4—O1—O3^ii	18.0 (9)
C7—N1—C1—C6	1.1 (4)	O1^ii—N4—O1—O3^ii	103.2 (4)
Cu1—N1—C1—C6	−172.2 (2)	O3—N4—O1—O3^ii	−161.5 (8)
C6—C1—C2—C3	−0.2 (6)	O2^ii—N4—O2—O3^ii	86.5 (8)
N1—C1—C2—C3	177.5 (4)	O1—N4—O2—O3^ii	−22.7 (11)
C1—C2—C3—C4	1.7 (6)	O1^ii—N4—O2—O3^ii	−147.3 (13)
C2—C3—C4—C5	−1.6 (7)	O3—N4—O2—O3^ii	156.7 (10)
C3—C4—C5—C6	−0.2 (6)	O2^ii—N4—O2—O1^ii	−126.2 (8)
C7—N2—C6—C1	−1.1 (4)	O1—N4—O2—O1^ii	124.6 (10)
C7—N2—C6—C5	178.6 (4)	O3—N4—O2—O1^ii	−56.0 (9)
C2—C1—C6—N2	178.2 (3)	O3^ii—N4—O2—O1^ii	147.3 (13)
N1—C1—C6—N2	0.0 (4)	O2—N4—O3—O2^ii	−151.8 (13)
C2—C1—C6—C5	−1.6 (6)	O1—N4—O3—O2^ii	27.8 (12)
N1—C1—C6—C5	−179.7 (3)	O1^ii—N4—O3—O2^ii	163.9 (8)
C4—C5—C6—N2	−178.0 (4)	O3^ii—N4—O3—O2^ii	−82.6 (8)
C4—C5—C6—C1	1.7 (6)	O2^ii—N4—O3—O1^ii	−163.9 (8)
C1—N1—C7—N2	−1.8 (4)	O2—N4—O3—O1^ii	44.3 (8)
Cu1—N1—C7—N2	171.6 (2)	O1—N4—O3—O1^ii	−136.1 (8)
C1—N1—C7—C8	178.0 (3)	O3^ii—N4—O3—O1^ii	113.5 (4)
Cu1—N1—C7—C8	−8.6 (5)

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