Crystal structure and Hirshfeld surface analysis of 6,6′-dimethyl-2,2′-bi­pyridine-1,1′-diium tetra­chlorido­cobaltate(II)

The title salt features N—H...Cl and C—H...Cl cation-to-anion hydrogen bonds and complementary anion-to-cation Cl...π inter­actions.

Computing details

6,6'-Dimethyl-2,2'-bipyridine-1,1'-diium tetrachloridocobaltate(II)

Crystal data

(C12H14N2)[CoCl4]	Z = 2
Mr = 386.98	F(000) = 390
Triclinic, P1	Dx = 1.653 Mg m^−3
a = 6.6419 (16) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.6512 (19) Å	Cell parameters from 9272 reflections
c = 15.837 (4) Å	θ = 2.7–28.6°
α = 99.458 (6)°	µ = 1.78 mm^−1
β = 98.020 (6)°	T = 301 K
γ = 97.046 (6)°	Block, blue
V = 777.3 (3) Å^3	0.21 × 0.11 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer	3661 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.041
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θmax = 28.6°, θmin = 2.7°
Tmin = 0.625, Tmax = 0.746	h = −8→8
13285 measured reflections	k = −10→10
3890 independent reflections	l = −21→21

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.081	w = 1/[σ^2(Fo^2) + (0.0415P)^2 + 0.2392P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.002
3890 reflections	Δρmax = 0.41 e Å^−3
180 parameters	Δρmin = −0.36 e Å^−3
0 restraints

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.

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

	x	y	z	Uiso*/Ueq
Co1	0.83193 (3)	0.11776 (3)	0.75825 (2)	0.02835 (8)
Cl1	0.50544 (6)	0.08040 (5)	0.79190 (3)	0.03681 (10)
Cl2	1.04301 (7)	0.30332 (6)	0.87001 (3)	0.04763 (12)
Cl3	0.82188 (7)	0.26717 (7)	0.64540 (3)	0.04459 (11)
Cl4	0.91033 (8)	−0.16382 (6)	0.71718 (3)	0.04905 (12)
N1	0.34377 (19)	0.34550 (17)	0.66800 (8)	0.0288 (2)
H1	0.371 (3)	0.276 (3)	0.7098 (14)	0.043*
N2	0.2849 (2)	0.69414 (16)	0.82797 (8)	0.0295 (2)
H2	0.178 (3)	0.719 (3)	0.7963 (14)	0.044*
C1	0.2787 (3)	0.0670 (3)	0.56372 (13)	0.0511 (5)
H1A	0.235167	0.025817	0.502509	0.077*
H1B	0.181069	0.013236	0.594770	0.077*
H1C	0.411174	0.033861	0.580711	0.077*
C2	0.2923 (2)	0.2659 (2)	0.58417 (10)	0.0351 (3)
C3	0.2537 (3)	0.3744 (3)	0.52323 (11)	0.0432 (4)
H3	0.220294	0.323926	0.464580	0.052*
C4	0.2648 (3)	0.5561 (3)	0.54950 (11)	0.0465 (4)
H4	0.239832	0.628226	0.508449	0.056*
C5	0.3130 (3)	0.6328 (2)	0.63697 (11)	0.0386 (3)
H5	0.317851	0.755367	0.655242	0.046*
C6	0.3535 (2)	0.52315 (19)	0.69586 (9)	0.0276 (3)
C7	0.4097 (2)	0.58981 (18)	0.79017 (9)	0.0276 (3)
C8	0.5805 (3)	0.5515 (2)	0.83936 (11)	0.0360 (3)
H8	0.669290	0.481996	0.814006	0.043*
C9	0.6170 (3)	0.6193 (2)	0.92811 (11)	0.0440 (4)
H9	0.731908	0.595592	0.962668	0.053*
C10	0.4840 (3)	0.7213 (2)	0.96494 (10)	0.0441 (4)
H10	0.507794	0.764127	1.024450	0.053*
C11	0.3147 (3)	0.7606 (2)	0.91364 (10)	0.0368 (3)
C12	0.1623 (4)	0.8715 (3)	0.94657 (14)	0.0555 (5)
H12A	0.186823	0.894239	1.008855	0.083*
H12B	0.025769	0.808301	0.925793	0.083*
H12C	0.176477	0.983126	0.926248	0.083*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.02780 (12)	0.03196 (12)	0.02530 (12)	0.00566 (8)	0.00268 (8)	0.00579 (8)
Cl1	0.03370 (19)	0.03675 (19)	0.0430 (2)	0.00376 (14)	0.01266 (15)	0.01194 (15)
Cl2	0.0492 (2)	0.0456 (2)	0.0389 (2)	−0.00486 (18)	−0.01213 (18)	0.00607 (17)
Cl3	0.0398 (2)	0.0659 (3)	0.0347 (2)	0.00992 (19)	0.00815 (16)	0.02524 (19)
Cl4	0.0507 (3)	0.0430 (2)	0.0507 (3)	0.02070 (19)	0.00004 (19)	−0.00242 (18)
N1	0.0270 (6)	0.0315 (6)	0.0266 (6)	0.0068 (5)	0.0002 (4)	0.0032 (5)
N2	0.0350 (6)	0.0275 (6)	0.0265 (6)	0.0043 (5)	0.0051 (5)	0.0068 (4)
C1	0.0499 (10)	0.0451 (10)	0.0481 (10)	0.0075 (8)	0.0000 (8)	−0.0142 (8)
C2	0.0264 (7)	0.0447 (8)	0.0298 (7)	0.0061 (6)	0.0014 (5)	−0.0034 (6)
C3	0.0377 (8)	0.0659 (11)	0.0241 (7)	0.0080 (8)	0.0028 (6)	0.0040 (7)
C4	0.0482 (10)	0.0668 (12)	0.0301 (8)	0.0134 (9)	0.0054 (7)	0.0224 (8)
C5	0.0462 (9)	0.0390 (8)	0.0343 (8)	0.0109 (7)	0.0058 (7)	0.0149 (6)
C6	0.0266 (6)	0.0315 (7)	0.0253 (6)	0.0063 (5)	0.0031 (5)	0.0062 (5)
C7	0.0312 (7)	0.0250 (6)	0.0257 (6)	0.0018 (5)	0.0020 (5)	0.0061 (5)
C8	0.0353 (8)	0.0330 (7)	0.0371 (8)	0.0045 (6)	−0.0039 (6)	0.0078 (6)
C9	0.0470 (9)	0.0429 (9)	0.0355 (8)	−0.0034 (7)	−0.0117 (7)	0.0117 (7)
C10	0.0619 (11)	0.0393 (8)	0.0247 (7)	−0.0076 (8)	0.0003 (7)	0.0045 (6)
C11	0.0511 (9)	0.0294 (7)	0.0298 (7)	−0.0015 (6)	0.0123 (7)	0.0058 (6)
C12	0.0712 (14)	0.0506 (11)	0.0466 (10)	0.0094 (10)	0.0273 (10)	−0.0002 (8)

Geometric parameters (Å, º)

Co1—Cl2	2.2600 (6)	C4—C5	1.389 (2)
Co1—Cl3	2.2720 (6)	C4—H4	0.9300
Co1—Cl4	2.2901 (7)	C5—C6	1.374 (2)
Co1—Cl1	2.2997 (7)	C5—H5	0.9300
N1—C2	1.3441 (19)	C6—C7	1.4758 (19)
N1—C6	1.3490 (19)	C7—C8	1.375 (2)
N1—H1	0.93 (2)	C8—C9	1.392 (2)
N2—C11	1.346 (2)	C8—H8	0.9300
N2—C7	1.3511 (19)	C9—C10	1.376 (3)
N2—H2	0.87 (2)	C9—H9	0.9300
C1—C2	1.492 (3)	C10—C11	1.387 (3)
C1—H1A	0.9600	C10—H10	0.9300
C1—H1B	0.9600	C11—C12	1.492 (3)
C1—H1C	0.9600	C12—H12A	0.9600
C2—C3	1.390 (3)	C12—H12B	0.9600
C3—C4	1.374 (3)	C12—H12C	0.9600
C3—H3	0.9300
Cl2—Co1—Cl3	105.46 (3)	C6—C5—C4	118.36 (16)
Cl2—Co1—Cl4	117.91 (2)	C6—C5—H5	120.8
Cl3—Co1—Cl4	110.39 (2)	C4—C5—H5	120.8
Cl2—Co1—Cl1	108.93 (2)	N1—C6—C5	119.83 (14)
Cl3—Co1—Cl1	107.287 (19)	N1—C6—C7	116.98 (12)
Cl4—Co1—Cl1	106.46 (2)	C5—C6—C7	123.19 (14)
C2—N1—C6	123.47 (14)	N2—C7—C8	119.92 (14)
C2—N1—H1	119.4 (14)	N2—C7—C6	116.93 (13)
C6—N1—H1	117.1 (14)	C8—C7—C6	123.15 (14)
C11—N2—C7	123.32 (14)	C7—C8—C9	118.30 (16)
C11—N2—H2	117.4 (14)	C7—C8—H8	120.9
C7—N2—H2	119.2 (14)	C9—C8—H8	120.9
C2—C1—H1A	109.5	C10—C9—C8	120.32 (16)
C2—C1—H1B	109.5	C10—C9—H9	119.8
H1A—C1—H1B	109.5	C8—C9—H9	119.8
C2—C1—H1C	109.5	C9—C10—C11	120.25 (15)
H1A—C1—H1C	109.5	C9—C10—H10	119.9
H1B—C1—H1C	109.5	C11—C10—H10	119.9
N1—C2—C3	117.74 (15)	N2—C11—C10	117.86 (16)
N1—C2—C1	117.33 (16)	N2—C11—C12	117.45 (17)
C3—C2—C1	124.93 (16)	C10—C11—C12	124.69 (17)
C4—C3—C2	120.12 (15)	C11—C12—H12A	109.5
C4—C3—H3	119.9	C11—C12—H12B	109.5
C2—C3—H3	119.9	H12A—C12—H12B	109.5
C3—C4—C5	120.43 (16)	C11—C12—H12C	109.5
C3—C4—H4	119.8	H12A—C12—H12C	109.5
C5—C4—H4	119.8	H12B—C12—H12C	109.5
C6—N1—C2—C3	2.1 (2)	N1—C6—C7—N2	−128.78 (14)
C6—N1—C2—C1	−177.24 (15)	C5—C6—C7—N2	51.6 (2)
N1—C2—C3—C4	−1.2 (3)	N1—C6—C7—C8	51.7 (2)
C1—C2—C3—C4	178.05 (18)	C5—C6—C7—C8	−127.95 (17)
C2—C3—C4—C5	−0.5 (3)	N2—C7—C8—C9	1.4 (2)
C3—C4—C5—C6	1.4 (3)	C6—C7—C8—C9	−179.06 (15)
C2—N1—C6—C5	−1.2 (2)	C7—C8—C9—C10	0.3 (3)
C2—N1—C6—C7	179.19 (14)	C8—C9—C10—C11	−1.4 (3)
C4—C5—C6—N1	−0.6 (2)	C7—N2—C11—C10	1.0 (2)
C4—C5—C6—C7	178.99 (15)	C7—N2—C11—C12	−179.01 (15)
C11—N2—C7—C8	−2.1 (2)	C9—C10—C11—N2	0.8 (2)
C11—N2—C7—C6	178.36 (14)	C9—C10—C11—C12	−179.26 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1	0.93 (2)	2.32 (2)	3.2205 (16)	164.5 (18)
N2—H2···Cl4^i	0.87 (2)	2.38 (2)	3.2436 (16)	171 (2)
C4—H4···Cl3^ii	0.93	2.68	3.571 (2)	161
C9—H9···Cl2^iii	0.93	2.79	3.565 (2)	141

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