Structural characterization and Hirshfeld surface analysis of a Co^II complex with imidazo[1,2-a]pyridine

The complex [CoL₂Cl₂] (L = imidazo[1,2-a]pyridine) exhibits a supra­molecular-layered assembly through π–π stacking inter­actions. The overall inter­molecular inter­actions involved in the structure have been qu­anti­fied and fully described by Hirshfeld surface analysis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.024
• wR factor = 0.064
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for   C4       --C5        .       10.5 s.u.

Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5       ..CL1              2.89 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7       ..CL1              2.88 Ang.

Alert level G
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        88% Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007) and SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007) and XPREP (Bruker, 2007); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006) and Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2009).

Dichloridobis(imidazo[1,2-a]pyridine-κN¹)cobalt(II)

Crystal data

[CoCl2(C7H6N2)2]	F(000) = 370
Mr = 366.11	Dx = 1.636 Mg m^−3
Monoclinic, P2/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.712 (2) Å	Cell parameters from 647 reflections
b = 6.7898 (18) Å	θ = 1.5–25.0°
c = 14.348 (4) Å	µ = 1.51 mm^−1
β = 98.533 (5)°	T = 293 K
V = 743.0 (4) Å^3	Block, pink
Z = 2	0.17 × 0.11 × 0.06 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer	1307 independent reflections
Radiation source: fine-focus sealed tube	1241 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ω and φ scans	θmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −8→9
Tmin = 0.82, Tmax = 0.92	k = −8→8
6663 measured reflections	l = −17→17

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.064	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0355P)^2 + 0.2499P] where P = (Fo^2 + 2Fc^2)/3
1307 reflections	(Δ/σ)max < 0.001
96 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Co1	0.250000	0.21247 (5)	0.750000	0.03788 (13)
Cl1	0.00699 (6)	0.40150 (8)	0.73557 (4)	0.05261 (16)
N1	0.2270 (2)	0.0373 (2)	0.63532 (10)	0.0410 (3)
N2	0.2373 (2)	−0.0539 (2)	0.48712 (11)	0.0452 (4)
C2	0.3250 (3)	0.2781 (3)	0.52292 (15)	0.0513 (5)
H2	0.341071	0.383348	0.564797	0.062*
C1	0.2664 (2)	0.0958 (3)	0.55145 (12)	0.0386 (4)
C6	0.1741 (3)	−0.2106 (3)	0.53192 (17)	0.0554 (5)
H6	0.141218	−0.332623	0.505604	0.066*
C5	0.2770 (3)	−0.0324 (4)	0.39615 (14)	0.0635 (6)
H5	0.261300	−0.136802	0.353786	0.076*
C7	0.1689 (3)	−0.1537 (3)	0.62194 (16)	0.0503 (5)
H7	0.131285	−0.232355	0.668094	0.060*
C3	0.3582 (3)	0.2988 (4)	0.43289 (15)	0.0629 (6)
H3	0.394972	0.419967	0.412794	0.075*
C4	0.3379 (3)	0.1406 (5)	0.37060 (15)	0.0677 (7)
H4	0.367003	0.155512	0.310375	0.081*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0447 (2)	0.0343 (2)	0.0365 (2)	0.000	0.01225 (14)	0.000
Cl1	0.0507 (3)	0.0496 (3)	0.0578 (3)	0.0098 (2)	0.0093 (2)	0.0003 (2)
N1	0.0469 (8)	0.0342 (8)	0.0436 (8)	−0.0029 (6)	0.0121 (7)	−0.0024 (6)
N2	0.0415 (8)	0.0476 (9)	0.0451 (9)	0.0027 (7)	0.0022 (7)	−0.0107 (7)
C2	0.0594 (12)	0.0493 (11)	0.0442 (11)	−0.0098 (9)	0.0045 (9)	0.0033 (9)
C1	0.0383 (9)	0.0406 (10)	0.0367 (9)	0.0018 (7)	0.0049 (7)	−0.0037 (7)
C6	0.0561 (12)	0.0403 (11)	0.0677 (14)	−0.0017 (9)	0.0023 (10)	−0.0165 (9)
C5	0.0534 (12)	0.0963 (18)	0.0387 (11)	0.0085 (13)	−0.0003 (9)	−0.0252 (12)
C7	0.0520 (11)	0.0353 (9)	0.0644 (12)	−0.0050 (9)	0.0109 (9)	0.0038 (9)
C3	0.0607 (13)	0.0808 (16)	0.0454 (11)	−0.0161 (12)	0.0019 (10)	0.0154 (11)
C4	0.0540 (13)	0.111 (2)	0.0381 (11)	−0.0105 (14)	0.0054 (9)	0.0056 (13)

Geometric parameters (Å, º)

Co1—N1	2.0168 (4)	C2—C1	1.400 (3)
Co1—N1^i	2.0169 (15)	C2—H2	0.9300
Co1—Cl1	2.2556 (5)	C6—C7	1.355 (3)
Co1—Cl1^i	2.2556 (7)	C6—H6	0.9300
N1—C1	1.344 (2)	C5—C4	1.337 (4)
N1—C7	1.376 (2)	C5—H5	0.9300
N2—C1	1.369 (2)	C7—H7	0.9300
N2—C6	1.370 (3)	C3—C4	1.391 (4)
N2—C5	1.392 (3)	C3—H3	0.9300
C2—C3	1.361 (3)	C4—H4	0.9300
N1—Co1—N1^i	107.70 (5)	N2—C1—C2	119.15 (17)
N1—Co1—Cl1	106.83 (1)	C7—C6—N2	106.79 (17)
N1^i—Co1—Cl1	112.44 (5)	C7—C6—H6	126.6
N1—Co1—Cl1^i	112.44 (5)	N2—C6—H6	126.6
N1^i—Co1—Cl1^i	106.83 (5)	C4—C5—N2	119.0 (2)
Cl1—Co1—Cl1^i	110.64 (4)	C4—C5—H5	120.5
C1—N1—C7	105.44 (16)	N2—C5—H5	120.5
C1—N1—Co1	123.48 (12)	C6—C7—N1	110.28 (19)
C7—N1—Co1	131.06 (14)	C6—C7—H7	124.9
C1—N2—C6	107.13 (16)	N1—C7—H7	124.9
C1—N2—C5	121.17 (19)	C2—C3—C4	120.7 (2)
C6—N2—C5	131.65 (19)	C2—C3—H3	119.6
C3—C2—C1	118.9 (2)	C4—C3—H3	119.6
C3—C2—H2	120.5	C5—C4—C3	120.9 (2)
C1—C2—H2	120.5	C5—C4—H4	119.6
N1—C1—N2	110.35 (16)	C3—C4—H4	119.6
N1—C1—C2	130.48 (17)
N1^i—Co1—N1—C1	−157.31 (17)	C5—N2—C1—C2	4.7 (3)
Cl1^i—Co1—N1—C1	−39.88 (15)	C3—C2—C1—N1	179.1 (2)
Cl1—Co1—N1—C1	81.68 (14)	C3—C2—C1—N2	−2.6 (3)
N1^i—Co1—N1—C7	24.35 (15)	C1—N2—C6—C7	−0.9 (2)
Cl1^i—Co1—N1—C7	141.78 (16)	C5—N2—C6—C7	176.8 (2)
Cl1—Co1—N1—C7	−96.66 (17)	C1—N2—C5—C4	−2.7 (3)
C7—N1—C1—N2	−1.1 (2)	C6—N2—C5—C4	180.0 (2)
Co1—N1—C1—N2	−179.77 (11)	N2—C6—C7—N1	0.2 (2)
C7—N1—C1—C2	177.4 (2)	C1—N1—C7—C6	0.5 (2)
Co1—N1—C1—C2	−1.3 (3)	Co1—N1—C7—C6	179.08 (14)
C6—N2—C1—N1	1.2 (2)	C1—C2—C3—C4	−1.3 (3)
C5—N2—C1—N1	−176.69 (16)	N2—C5—C4—C3	−1.3 (3)
C6—N2—C1—C2	−177.42 (18)	C2—C3—C4—C5	3.4 (4)

Symmetry code: (i) −x+1/2, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cl1^ii	0.93	2.89	3.663 (1)	141
C7—H7···Cl1^iii	0.93	2.88	3.734 (1)	153

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