Bis[1-(but-2-en­yl)-5-nitro-1H-benzimidazole-κN³]dichloro­cobalt(II)

The title compound, [CoCl₂(C₁₁H₁₁N₃O₂)₂], was synthesized from 1-(but-2-en­yl)-5-nitro­benzimidazole and cobalt dichloride in ethanol. The Co^II atom has a distorted tetra­hedral geometry, coordinated by two Cl atoms and two N atoms. The mol­ecule is located on a twofold rotation axis, which passes through the Co atom. In the crystal structure, mol­ecules are connected by inter­molecular C—H...O hydrogen-bonding inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.043
• wR factor = 0.114
• Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.95
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.23 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.70 Ratio
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Co1    -   Cl1     ..      19.89 su

Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           27.85
           From the CIF: _diffrn_reflns_theta_full          27.85
           From the CIF: _reflns_number_total               2882
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         3039
           Completeness (_total/calc)             94.83%
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ......       2.50 Sigma
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.62 mm
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C11

   0 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
   6 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
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Bis[1-(but-2-enyl)-5-nitro-1H-benzimidazole-κN³]dichlorocobalt(II)

Crystal data

[CoCl2(C11H11N3O2)2]	F(000) = 1156
Mr = 564.29	Dx = 1.463 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 33960 reflections
a = 15.9533 (11) Å	θ = 2.3–28.0°
b = 11.4385 (6) Å	µ = 0.92 mm^−1
c = 15.4545 (10) Å	T = 296 K
β = 114.736 (5)°	Prism, violet
V = 2561.4 (3) Å^3	0.62 × 0.47 × 0.38 mm
Z = 4

Data collection

Stoe IPDS-II diffractometer	2882 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2297 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.069
Detector resolution: 6.67 pixels mm^-1	θmax = 27.9°, θmin = 2.3°
ω scans	h = −20→20
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −15→15
Tmin = 0.600, Tmax = 0.722	l = −20→20
21773 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.114	w = 1/[σ^2(Fo^2) + (0.0636P)^2 + 1.122P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
2882 reflections	Δρmax = 0.50 e Å^−3
160 parameters	Δρmin = −0.34 e Å^−3
0 restraints	Extinction correction: SHELXL97, FC^*=KFC[1+0.001XFC^2Λ^3/sin(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0010 (4)

Special details

Experimental. ¹H NMR (DMSO-d₆): δ 1.3 (d, CH₃, 6H), 3.9 (d, CH₂, 4H), 5.1 (m, CH═, 4H), 7.3 (m, Ar–H, 6H), 8.8 (s, CH, 2H).

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 (Ų)

	x	y	z	Uiso*/Ueq
Co1	0.00000	0.64594 (4)	0.25000	0.0460 (2)
Cl1	−0.11978 (5)	0.75331 (6)	0.14718 (5)	0.0603 (2)
O1	0.30755 (19)	0.8155 (2)	0.1932 (2)	0.0879 (10)
O2	0.3580 (3)	0.7308 (3)	0.1032 (4)	0.141 (2)
N1	0.04819 (13)	0.53550 (16)	0.17823 (14)	0.0454 (6)
N2	0.05380 (13)	0.38412 (16)	0.09071 (14)	0.0437 (5)
N3	0.30685 (19)	0.7352 (2)	0.1425 (3)	0.0736 (10)
C1	0.12006 (14)	0.55327 (18)	0.15094 (16)	0.0423 (6)
C2	0.18051 (15)	0.64673 (19)	0.16830 (18)	0.0471 (7)
C3	0.24177 (17)	0.6375 (2)	0.1269 (2)	0.0540 (8)
C4	0.24722 (19)	0.5439 (3)	0.0730 (2)	0.0639 (10)
C5	0.18771 (17)	0.4508 (2)	0.0565 (2)	0.0547 (8)
C6	0.12390 (15)	0.45859 (19)	0.09595 (16)	0.0436 (6)
C7	0.01250 (15)	0.43364 (19)	0.14107 (18)	0.0472 (7)
C8	0.02990 (18)	0.2712 (2)	0.04043 (19)	0.0512 (7)
C9	0.0891 (2)	0.1724 (2)	0.0941 (2)	0.0727 (10)
C10	0.0618 (4)	0.0769 (3)	0.1138 (3)	0.0990 (15)
C11	0.1178 (5)	−0.0264 (4)	0.1601 (4)	0.179 (3)
H2	0.17970	0.71070	0.20510	0.0570*
H4	0.29100	0.54370	0.04790	0.0770*
H5	0.19000	0.38640	0.02090	0.0660*
H7	−0.03670	0.39950	0.14910	0.0570*
H8A	0.03440	0.27890	−0.02000	0.0610*
H8B	−0.03380	0.25280	0.02680	0.0610*
H9	0.15250	0.18190	0.11520	0.0870*
H10	−0.00120	0.07080	0.09700	0.1190*
H11A	0.07850	−0.08670	0.16560	0.2680*
H11B	0.16270	−0.00530	0.22250	0.2680*
H11C	0.14870	−0.05430	0.12260	0.2680*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0508 (3)	0.0394 (2)	0.0533 (3)	0.0000	0.0272 (2)	0.0000
Cl1	0.0694 (4)	0.0642 (4)	0.0481 (4)	0.0284 (3)	0.0254 (3)	0.0092 (2)
O1	0.0908 (16)	0.0681 (13)	0.112 (2)	−0.0349 (12)	0.0495 (15)	−0.0199 (14)
O2	0.136 (3)	0.114 (2)	0.244 (5)	−0.063 (2)	0.150 (4)	−0.048 (3)
N1	0.0459 (9)	0.0389 (9)	0.0576 (11)	−0.0017 (7)	0.0279 (8)	−0.0003 (8)
N2	0.0443 (9)	0.0368 (8)	0.0513 (10)	−0.0028 (7)	0.0214 (8)	−0.0001 (7)
N3	0.0636 (15)	0.0662 (15)	0.102 (2)	−0.0201 (11)	0.0455 (15)	−0.0009 (14)
C1	0.0403 (10)	0.0386 (10)	0.0491 (12)	0.0017 (8)	0.0199 (9)	0.0050 (8)
C2	0.0449 (11)	0.0411 (10)	0.0558 (13)	−0.0032 (8)	0.0215 (10)	0.0017 (9)
C3	0.0467 (12)	0.0504 (12)	0.0678 (15)	−0.0110 (9)	0.0267 (11)	0.0014 (11)
C4	0.0566 (14)	0.0682 (16)	0.0823 (19)	−0.0068 (12)	0.0444 (14)	−0.0031 (14)
C5	0.0525 (13)	0.0531 (13)	0.0667 (15)	−0.0013 (10)	0.0329 (12)	−0.0061 (11)
C6	0.0428 (10)	0.0397 (10)	0.0491 (12)	0.0012 (8)	0.0201 (9)	0.0033 (8)
C7	0.0444 (11)	0.0418 (10)	0.0590 (14)	−0.0038 (8)	0.0252 (10)	0.0009 (9)
C8	0.0555 (13)	0.0434 (11)	0.0533 (14)	−0.0071 (9)	0.0215 (11)	−0.0061 (9)
C9	0.0820 (19)	0.0470 (14)	0.0711 (19)	0.0020 (13)	0.0142 (15)	−0.0061 (12)
C10	0.134 (3)	0.0503 (17)	0.088 (3)	−0.0097 (18)	0.022 (2)	0.0012 (16)
C11	0.255 (8)	0.050 (2)	0.122 (4)	0.010 (3)	−0.028 (5)	0.007 (2)

Geometric parameters (Å, º)

Co1—Cl1	2.2680 (8)	C4—C5	1.378 (4)
Co1—N1	2.032 (2)	C5—C6	1.391 (4)
Co1—Cl1^i	2.2680 (8)	C8—C9	1.484 (4)
Co1—N1^i	2.032 (2)	C9—C10	1.260 (5)
O1—N3	1.204 (4)	C10—C11	1.474 (7)
O2—N3	1.205 (7)	C2—H2	0.9300
N1—C1	1.392 (3)	C4—H4	0.9300
N1—C7	1.318 (3)	C5—H5	0.9300
N2—C6	1.381 (3)	C7—H7	0.9300
N2—C7	1.338 (3)	C8—H8A	0.9700
N2—C8	1.473 (3)	C8—H8B	0.9700
N3—C3	1.475 (4)	C9—H9	0.9300
C1—C2	1.389 (3)	C10—H10	0.9300
C1—C6	1.394 (3)	C11—H11A	0.9600
C2—C3	1.378 (4)	C11—H11B	0.9600
C3—C4	1.381 (4)	C11—H11C	0.9600
Co1···H2	3.3000	C7···C7^i	3.552 (4)
Co1···H2^i	3.3000	C7···O1^vii	3.236 (4)
Cl1···N1^i	3.495 (2)	C8···O2^ix	3.302 (6)
Cl1···C2^i	3.587 (3)	C8···C1^iii	3.547 (3)
Cl1···C5^ii	3.591 (3)	C9···O1^vii	3.416 (4)
Cl1···H5^iii	2.8500	C11···O1^x	3.376 (8)
Cl1···H8A^iii	2.8500	C2···H11B^v	2.9300
Cl1···H2^i	2.8600	C3···H11B^v	2.7300
O1···C11^iv	3.376 (8)	C4···H11B^v	2.9300
O1···C6^v	3.393 (4)	C5···H8A	2.9700
O1···C7^v	3.236 (4)	C8···H5	3.0000
O1···N2^v	3.237 (3)	H2···Co1	3.3000
O1···C9^v	3.416 (4)	H2···O1	2.4400
O2···C7^vi	3.255 (5)	H2···Cl1^i	2.8600
O2···C8^vi	3.302 (6)	H4···O2	2.3900
O1···H2	2.4400	H5···C8	3.0000
O1···H11C^iv	2.7400	H5···Cl1^iii	2.8500
O2···H4	2.3900	H7···H8B	2.5400
O2···H7^vi	2.4600	H7···O2^ix	2.4600
O2···H8B^vi	2.4800	H8A···C5	2.9700
N1···N2	2.222 (3)	H8A···Cl1^iii	2.8500
N1···Cl1^i	3.495 (2)	H8B···H7	2.5400
N1···N1^i	3.184 (3)	H8B···H10	2.3000
N2···N1	2.222 (3)	H8B···O2^ix	2.4800
N2···O1^vii	3.237 (3)	H10···H8B	2.3000
C1···C8^iii	3.547 (3)	H11B···C2^vii	2.9300
C2···Cl1^i	3.587 (3)	H11B···C3^vii	2.7300
C5···Cl1^viii	3.591 (3)	H11B···C4^vii	2.9300
C6···O1^vii	3.393 (4)	H11C···O1^x	2.7400
C7···O2^ix	3.255 (5)
Cl1—Co1—N1	110.76 (6)	N1—C7—N2	113.6 (2)
Cl1—Co1—Cl1^i	114.43 (3)	N2—C8—C9	114.2 (2)
Cl1—Co1—N1^i	108.59 (6)	C8—C9—C10	126.3 (4)
Cl1^i—Co1—N1	108.59 (6)	C9—C10—C11	127.7 (6)
N1—Co1—N1^i	103.14 (8)	C1—C2—H2	123.00
Cl1^i—Co1—N1^i	110.76 (6)	C3—C2—H2	123.00
Co1—N1—C1	128.47 (15)	C3—C4—H4	120.00
Co1—N1—C7	126.44 (18)	C5—C4—H4	120.00
C1—N1—C7	104.9 (2)	C4—C5—H5	122.00
C6—N2—C7	106.77 (19)	C6—C5—H5	122.00
C6—N2—C8	126.6 (2)	N1—C7—H7	123.00
C7—N2—C8	126.6 (2)	N2—C7—H7	123.00
O1—N3—O2	122.4 (3)	N2—C8—H8A	109.00
O1—N3—C3	119.9 (3)	N2—C8—H8B	109.00
O2—N3—C3	117.7 (3)	C9—C8—H8A	109.00
N1—C1—C2	130.3 (2)	C9—C8—H8B	109.00
N1—C1—C6	108.9 (2)	H8A—C8—H8B	108.00
C2—C1—C6	120.8 (2)	C8—C9—H9	117.00
C1—C2—C3	114.9 (2)	C10—C9—H9	117.00
N3—C3—C2	117.0 (2)	C9—C10—H10	116.00
N3—C3—C4	117.9 (3)	C11—C10—H10	116.00
C2—C3—C4	125.1 (3)	C10—C11—H11A	109.00
C3—C4—C5	119.9 (3)	C10—C11—H11B	109.00
C4—C5—C6	116.3 (2)	C10—C11—H11C	110.00
N2—C6—C1	105.9 (2)	H11A—C11—H11B	109.00
N2—C6—C5	131.1 (2)	H11A—C11—H11C	110.00
C1—C6—C5	123.0 (2)	H11B—C11—H11C	110.00
Cl1—Co1—N1—C1	93.72 (19)	O1—N3—C3—C2	3.4 (5)
Cl1^i—Co1—N1—C1	−32.7 (2)	O2—N3—C3—C2	−176.7 (4)
N1^i—Co1—N1—C1	−150.28 (19)	O2—N3—C3—C4	3.8 (5)
Cl1—Co1—N1—C7	−80.8 (2)	O1—N3—C3—C4	−176.1 (3)
Cl1^i—Co1—N1—C7	152.80 (19)	N1—C1—C2—C3	−177.5 (2)
N1^i—Co1—N1—C7	35.3 (2)	C6—C1—C2—C3	0.5 (3)
Co1—N1—C1—C2	3.3 (4)	C2—C1—C6—C5	0.7 (4)
C7—N1—C1—C2	178.7 (3)	N1—C1—C6—N2	−0.1 (3)
Co1—N1—C1—C6	−174.81 (16)	C2—C1—C6—N2	−178.4 (2)
C7—N1—C1—C6	0.6 (3)	N1—C1—C6—C5	179.1 (2)
C1—N1—C7—N2	−1.0 (3)	C1—C2—C3—N3	179.4 (3)
Co1—N1—C7—N2	174.57 (16)	C1—C2—C3—C4	−1.2 (4)
C6—N2—C7—N1	0.9 (3)	C2—C3—C4—C5	0.7 (5)
C7—N2—C6—C1	−0.5 (3)	N3—C3—C4—C5	−179.9 (3)
C7—N2—C6—C5	−179.5 (3)	C3—C4—C5—C6	0.5 (4)
C8—N2—C6—C5	1.2 (4)	C4—C5—C6—N2	177.6 (3)
C8—N2—C6—C1	−179.8 (2)	C4—C5—C6—C1	−1.2 (4)
C6—N2—C8—C9	80.8 (3)	N2—C8—C9—C10	125.8 (4)
C7—N2—C8—C9	−98.4 (3)	C8—C9—C10—C11	174.7 (4)
C8—N2—C7—N1	−179.8 (2)

Symmetry codes: (i) −x, y, −z+1/2; (ii) x−1/2, y+1/2, z; (iii) −x, −y+1, −z; (iv) x, y+1, z; (v) −x+1/2, y+1/2, −z+1/2; (vi) x+1/2, y+1/2, z; (vii) −x+1/2, y−1/2, −z+1/2; (viii) x+1/2, y−1/2, z; (ix) x−1/2, y−1/2, z; (x) x, y−1, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O2^ix	0.93	2.46	3.255 (5)	143
C8—H8B···O2^ix	0.97	2.48	3.302 (6)	142

Symmetry code: (ix) x−1/2, y−1/2, z.