catena-Poly[copper(I)-μ-2-(2-pyrid­yl)-1H-benzimidazolato-κ²N¹:N³]

The chain structure of the title compound, [Cu(C₁₂H₈N₃)]_n, consists of alternating 2-(2-pyrid­yl)-1H-benzimidazolate anions and copper(I) cations. The chain, which has the Cu^I atom in a linear coordination geometry, runs along the a axis of the monoclinic unit cell.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma]() = 0.000 Å
• Disorder in main residue
• R factor = 0.041
• wR factor = 0.125
• Data-to-parameter ratio = 9.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT301_ALERT_3_B Main Residue  Disorder .........................      48.00 Perc.

Alert level C
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.40
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.53 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         N3
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         N6
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C24

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.

catena-Poly[copper(I)-µ-2-(2-pyridyl)-1H-benzimidazolato-κ²N¹:N³]

Crystal data

[Cu(C12H8N3)]	F(000) = 520
Mr = 257.75	Dx = 1.707 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 886 reflections
a = 5.858 (1) Å	θ = 2.8–27.0°
b = 22.090 (3) Å	µ = 2.15 mm^−1
c = 8.212 (1) Å	T = 295 K
β = 109.255 (2)°	Rod, yellow
V = 1003.2 (2) Å^3	0.21 × 0.12 × 0.10 mm
Z = 4

Data collection

Bruker SMART 1K area-detector diffractometer	2181 independent reflections
Radiation source: fine-focus sealed tube	1913 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
φ and ω scans	θmax = 27.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.661, Tmax = 0.814	k = −25→28
6798 measured reflections	l = −10→10

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.125	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.084P)^2 + 0.692P] where P = (Fo^2 + 2Fc^2)/3
2181 reflections	(Δ/σ)max = 0.001
232 parameters	Δρmax = 0.53 e Å^−3
200 restraints	Δρmin = −0.50 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.71214 (6)	0.53306 (2)	0.70560 (5)	0.0371 (2)
N1	0.4132 (7)	0.5089 (2)	0.7310 (6)	0.032 (1)	0.50
N2	0.0394 (7)	0.5130 (2)	0.7431 (6)	0.032 (1)	0.50
N3	0.2609 (7)	0.6171 (2)	0.4830 (5)	0.053 (1)	0.50
N4	1.0094 (8)	0.5532 (2)	0.6777 (7)	0.037 (1)	0.50
N5	1.3862 (7)	0.5547 (2)	0.6723 (7)	0.035 (1)	0.50
N6	1.1388 (8)	0.4468 (2)	0.9032 (6)	0.052 (2)	0.50
C1	0.3751 (7)	0.4574 (2)	0.8091 (5)	0.033 (1)	0.50
C2	0.5226 (6)	0.4086 (2)	0.8832 (6)	0.041 (1)	0.50
C3	0.4372 (8)	0.3632 (2)	0.9653 (7)	0.052 (2)	0.50
C4	0.2043 (9)	0.3667 (2)	0.9734 (7)	0.048 (2)	0.50
C5	0.0567 (7)	0.4155 (2)	0.8993 (7)	0.047 (2)	0.50
C6	0.1421 (6)	0.4608 (2)	0.8172 (6)	0.033 (1)	0.50
C7	0.210 (1)	0.5415 (3)	0.6953 (17)	0.029 (2)	0.50
C8	0.1723 (8)	0.6011 (1)	0.6147 (5)	0.028 (1)	0.50
C9	0.0411 (8)	0.6428 (2)	0.6748 (5)	0.038 (1)	0.50
C10	−0.0016 (8)	0.7004 (2)	0.6034 (6)	0.032 (1)	0.50
C11	0.0870 (9)	0.7164 (1)	0.4717 (6)	0.052 (2)	0.50
C12	0.2182 (9)	0.6748 (2)	0.4116 (6)	0.046 (1)	0.50
C13	1.0465 (7)	0.6074 (2)	0.6141 (6)	0.039 (1)	0.50
C14	0.8948 (6)	0.6566 (2)	0.5518 (8)	0.061 (2)	0.50
C15	0.9794 (8)	0.7069 (2)	0.4875 (9)	0.072 (3)	0.50
C16	1.2157 (9)	0.7080 (2)	0.4856 (8)	0.062 (2)	0.50
C17	1.3675 (6)	0.6589 (2)	0.5479 (7)	0.048 (2)	0.50
C18	1.2829 (6)	0.6085 (2)	0.6121 (6)	0.034 (1)	0.50
C19	1.217 (1)	0.5225 (3)	0.710 (2)	0.029 (2)	0.50
C20	1.2554 (9)	0.4616 (1)	0.7861 (6)	0.031 (1)	0.50
C21	1.4006 (8)	0.4191 (2)	0.7427 (5)	0.041 (1)	0.50
C22	1.4290 (8)	0.3617 (2)	0.8163 (6)	0.047 (2)	0.50
C23	1.3123 (9)	0.3469 (2)	0.9334 (6)	0.052 (2)	0.50
C24	1.1672 (9)	0.3894 (2)	0.9768 (6)	0.032 (2)	0.50
H2	0.6784	0.4063	0.8777	0.049*	0.50
H3	0.5359	0.3306	1.0148	0.062*	0.50
H4	0.1471	0.3363	1.0283	0.057*	0.50
H5	−0.0991	0.4178	0.9047	0.056*	0.50
H9	−0.0181	0.6321	0.7629	0.045*	0.50
H10	−0.0894	0.7283	0.6436	0.038*	0.50
H11	0.0584	0.7550	0.4239	0.063*	0.50
H12	0.2774	0.6855	0.3235	0.055*	0.50
H14	0.7367	0.6558	0.5530	0.073*	0.50
H15	0.8779	0.7398	0.4458	0.086*	0.50
H16	1.2723	0.7417	0.4426	0.074*	0.50
H17	1.5256	0.6596	0.5466	0.058*	0.50
H21	1.4786	0.4290	0.6644	0.049*	0.50
H22	1.5261	0.3333	0.7873	0.056*	0.50
H23	1.3313	0.3085	0.9826	0.062*	0.50
H24	1.0891	0.3795	1.0551	0.039*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0195 (2)	0.0444 (3)	0.0518 (3)	0.0022 (1)	0.0179 (2)	0.0032 (2)
N1	0.021 (2)	0.038 (2)	0.039 (2)	−0.002 (2)	0.015 (2)	−0.002 (2)
N2	0.019 (2)	0.036 (2)	0.043 (3)	0.001 (2)	0.013 (2)	0.001 (2)
C1	0.022 (3)	0.038 (3)	0.043 (3)	−0.003 (3)	0.017 (3)	−0.005 (2)
C2	0.029 (3)	0.044 (3)	0.050 (3)	0.007 (2)	0.013 (2)	−0.003 (3)
C3	0.051 (4)	0.033 (3)	0.065 (4)	0.004 (3)	0.011 (3)	0.006 (3)
C4	0.050 (4)	0.023 (4)	0.067 (4)	0.001 (3)	0.014 (3)	0.014 (3)
C5	0.039 (4)	0.036 (3)	0.069 (4)	−0.007 (3)	0.023 (3)	−0.001 (3)
C6	0.024 (3)	0.040 (3)	0.037 (3)	0.002 (2)	0.015 (3)	−0.001 (2)
C7	0.028 (4)	0.026 (5)	0.033 (3)	−0.001 (3)	0.011 (3)	−0.003 (4)
C8	0.015 (3)	0.036 (3)	0.039 (3)	−0.001 (3)	0.015 (3)	0.000 (2)
C9	0.036 (3)	0.043 (3)	0.038 (3)	0.001 (3)	0.017 (2)	−0.002 (3)
C10	0.034 (3)	0.027 (3)	0.041 (3)	0.007 (2)	0.021 (2)	0.001 (2)
C11	0.048 (4)	0.051 (4)	0.063 (4)	0.004 (4)	0.026 (4)	0.012 (3)
C12	0.050 (4)	0.046 (3)	0.049 (3)	0.000 (3)	0.027 (3)	0.012 (3)
N3	0.042 (3)	0.059 (3)	0.061 (4)	0.000 (3)	0.022 (3)	0.002 (3)
N4	0.022 (2)	0.041 (3)	0.056 (3)	−0.001 (2)	0.022 (2)	−0.003 (2)
N5	0.017 (2)	0.044 (3)	0.046 (3)	0.002 (2)	0.0130 (18)	0.002 (2)
C13	0.024 (3)	0.045 (3)	0.053 (3)	−0.003 (3)	0.020 (3)	−0.006 (3)
C14	0.042 (4)	0.044 (4)	0.104 (6)	0.008 (3)	0.034 (4)	0.004 (4)
C15	0.063 (5)	0.035 (4)	0.119 (7)	0.012 (4)	0.031 (5)	0.014 (4)
C16	0.050 (4)	0.040 (4)	0.095 (6)	0.004 (4)	0.024 (4)	0.013 (4)
C17	0.038 (3)	0.044 (3)	0.067 (4)	−0.009 (3)	0.024 (3)	−0.002 (3)
C18	0.022 (3)	0.040 (3)	0.042 (3)	−0.001 (2)	0.015 (3)	−0.002 (2)
C19	0.022 (3)	0.030 (5)	0.037 (4)	0.000 (3)	0.012 (2)	−0.004 (4)
C20	0.016 (3)	0.040 (3)	0.042 (3)	−0.002 (3)	0.017 (3)	−0.002 (2)
C21	0.036 (3)	0.045 (3)	0.049 (3)	0.003 (2)	0.024 (3)	0.001 (3)
C22	0.036 (3)	0.044 (3)	0.065 (4)	0.005 (3)	0.024 (3)	0.003 (3)
C23	0.048 (4)	0.051 (4)	0.059 (4)	0.007 (3)	0.021 (4)	0.008 (3)
C24	0.030 (3)	0.031 (4)	0.042 (3)	0.009 (3)	0.020 (2)	0.016 (3)
N6	0.038 (3)	0.066 (4)	0.052 (4)	0.000 (3)	0.016 (3)	−0.003 (4)

Geometric parameters (Å, º)

Cu1—N1	1.907 (4)	C14—C15	1.39
Cu1—N2^i	1.891 (4)	C15—C16	1.39
Cu1—N4	1.883 (4)	C15—H15	0.93
Cu1—N5^ii	1.899 (4)	C16—C17	1.39
N1—C7	1.340 (7)	C17—C18	1.39
N1—C1	1.360 (5)	C19—C20	1.468 (6)
N2—C7	1.342 (7)	C20—C21	1.39
N2—C6	1.349 (5)	C20—N6	1.39
C1—C2	1.39	C21—C22	1.39
C1—C6	1.39	C22—C23	1.39
C2—C3	1.39	C23—C24	1.39
C3—C4	1.39	C24—N6	1.39
C4—C5	1.39	C2—H2	0.93
C5—C6	1.39	C3—H3	0.93
C7—C8	1.458 (6)	C4—H4	0.93
C8—C9	1.39	C5—H5	0.93
C8—N3	1.39	C9—H9	0.93
C9—C10	1.39	C10—H10	0.93
C10—C11	1.39	C11—H11	0.93
C11—C12	1.39	C12—H12	0.93
C12—N3	1.39	C14—H14	0.93
N4—C19	1.339 (7)	C16—H16	0.93
N4—C13	1.352 (5)	C17—H17	0.93
N5—C19	1.339 (7)	C21—H21	0.93
N5—C18	1.352 (5)	C22—H22	0.93
C13—C14	1.39	C23—H23	0.93
C13—C18	1.39	C24—H24	0.93
N1—Cu1—N4	177.4 (2)	N4—C19—C20	123.5 (5)
N2^i—Cu1—N5^ii	178.6 (2)	N5—C19—C20	124.3 (5)
C7—N1—C1	106.3 (4)	C21—C20—N6	120.0
C7—N1—Cu1	127.5 (4)	C21—C20—C19	122.1 (5)
C1—N1—Cu1	125.8 (3)	N6—C20—C19	117.9 (5)
C7—N2—C6	105.6 (4)	C22—C21—C20	120.0
N1—C1—C2	132.8 (3)	C21—C22—C23	120.0
N1—C1—C6	107.1 (3)	C22—C23—C24	120.0
C2—C1—C6	120.0	N6—C24—C23	120.0
C3—C2—C1	120.0	C24—N6—C20	120.0
C2—C3—C4	120.0	C3—C2—H2	120.0
C3—C4—C5	120.0	C1—C2—H2	120.0
C6—C5—C4	120.0	C2—C3—H3	120.0
N2—C6—C5	131.1 (3)	C4—C3—H3	120.0
N2—C6—C1	108.9 (3)	C3—C4—H4	120.0
C5—C6—C1	120.0	C5—C4—H4	120.0
N1—C7—N2	112.2 (4)	C6—C5—H5	120.0
N1—C7—C8	125.0 (5)	C4—C5—H5	120.0
N2—C7—C8	122.8 (5)	C8—C9—H9	120.0
C9—C8—N3	120.0	C10—C9—H9	120.0
C9—C8—C7	117.0 (5)	C11—C10—H10	120.0
N3—C8—C7	123.0 (5)	C9—C10—H10	120.0
C8—C9—C10	120.0	C10—C11—H11	120.0
C11—C10—C9	120.0	C12—C11—H11	120.0
C10—C11—C12	120.0	N3—C12—H12	120.0
N3—C12—C11	120.0	C11—C12—H12	120.0
C12—N3—C8	120.0	C15—C14—H14	120.0
C19—N4—C13	105.9 (4)	C13—C14—H14	120.0
C19—N4—Cu1	132.1 (4)	C14—C15—H15	120.0
C13—N4—Cu1	122.0 (3)	C16—C15—H15	120.0
C19—N5—C18	106.0 (4)	C17—C16—H16	120.0
N4—C13—C14	132.0 (3)	C15—C16—H16	120.0
N4—C13—C18	108.0 (3)	C16—C17—H17	120.0
C14—C13—C18	120.0	C18—C17—H17	120.0
C15—C14—C13	120.0	C22—C21—H21	120.0
C14—C15—C16	120.0	C20—C21—H21	120.0
C17—C16—C15	120.0	C21—C22—H22	120.0
C16—C17—C18	120.0	C23—C22—H22	120.0
N5—C18—C17	132.0 (3)	C22—C23—H23	120.0
N5—C18—C13	107.9 (3)	C24—C23—H23	120.0
C17—C18—C13	120.0	N6—C24—H24	120.0
N4—C19—N5	112.2 (5)	C23—C24—H24	120.0
C7—N1—C1—C2	−175.8 (7)	C19—N4—C13—C14	177.0 (7)
Cu1—N1—C1—C2	−2.8 (7)	Cu1—N4—C13—C14	−2.9 (7)
C7—N1—C1—C6	0.2 (8)	C19—N4—C13—C18	−1.0 (8)
Cu1—N1—C1—C6	173.3 (3)	Cu1—N4—C13—C18	179.1 (3)
N1—C1—C2—C3	175.6 (5)	N4—C13—C14—C15	−177.8 (6)
C7—N2—C6—C5	175.5 (7)	C19—N5—C18—C17	−177.3 (7)
C7—N2—C6—C1	−1.7 (8)	Cu1^i—N5—C18—C17	5.6 (7)
C4—C5—C6—N2	−177.0 (6)	C19—N5—C18—C13	−0.3 (8)
N1—C1—C6—N2	0.9 (4)	Cu1^i—N5—C18—C13	−177.4 (3)
C2—C1—C6—N2	177.6 (4)	C16—C17—C18—N5	176.7 (6)
N1—C1—C6—C5	−176.6 (4)	N4—C13—C18—N5	0.9 (5)
C1—N1—C7—N2	−1 (1)	C14—C13—C18—N5	−177.4 (5)
Cu1—N1—C7—N2	−174.2 (5)	N4—C13—C18—C17	178.3 (5)
C1—N1—C7—C8	178 (1)	C13—N4—C19—N5	0.9 (12)
Cu1—N1—C7—C8	6 (2)	Cu1—N4—C19—N5	−179.3 (5)
C6—N2—C7—N1	2 (1)	C13—N4—C19—C20	178 (1)
C6—N2—C7—C8	−178 (1)	Cu1—N4—C19—C20	−2 (2)
N1—C7—C8—C9	−142 (1)	C18—N5—C19—N4	0 (1)
N2—C7—C8—C9	38 (1)	Cu1^i—N5—C19—N4	176.6 (6)
N1—C7—C8—N3	38 (2)	C18—N5—C19—C20	−177 (1)
N2—C7—C8—N3	−141.9 (9)	Cu1^i—N5—C19—C20	−1 (2)
C7—C8—C9—C10	−179.9 (7)	N4—C19—C20—C21	146.6 (9)
C7—C8—N3—C12	179.9 (7)	N5—C19—C20—C21	−37 (2)
N2^i—Cu1—N4—C19	8.1 (9)	N4—C19—C20—N6	−32 (1)
N5^ii—Cu1—N4—C19	−174.5 (9)	N5—C19—C20—N6	144.4 (9)
N2^i—Cu1—N4—C13	−172.1 (8)	C19—C20—C21—C22	−179.1 (7)
N5^ii—Cu1—N4—C13	5.3 (8)	C19—C20—N6—C24	179.1 (7)

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