trans-Bis[8-(benzyl­sulfan­yl)quinoline-κ2N,S]di­chlorido­cobalt(II)

Kodama, S.; Bunno, K.; Nomoto, A.; Ogawa, A.

doi:10.1107/S2414314621009925

trans-Bis[8-(benzylsulfanyl)quinoline-κ²N,S]dichloridocobalt(II)

S. Kodama, K. Bunno, A. Nomoto and A. Ogawa

The title dichlorocobalt(II) complex, trans-[CoCl₂(1)₂] [1 = 8-(benzylsulfanyl)quinoline, C₁₆H₁₃NS], has a central Co^II atom (site symmetry $\overline1$ ) that exhibits a distorted octahedral coordination geometry and is coordinated by two N and two S atoms from the bidentate N,S-ligand (1) situated in an equatorial plane and two Cl atoms in the axial positions. Complexes are linked by weak intermolecular C—H

π interactions between the 8-(benzylsulfanyl)quinoline ligands, forming a chain extending along the a-axis direction.

Keywords: crystal structure; cobalt(II) complex; bidentate N,S-ligand.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314621009925/zl4046sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2414314621009925/zl4046Isup2.hkl Contains datablock I

CCDC reference: 2111388

checkCIF report

Key indicators

Single-crystal X-ray study
T = 103 K
Mean (C-C) = 0.003 Å
R factor = 0.031
wR factor = 0.082
Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........  <I>CG</I> Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.654 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          8 Report
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          1 Check

Alert level G
PLAT794_ALERT_5_G Tentative Bond Valency for Co1       (II)      .       1.70 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          9 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         13 Info

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

   1 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
   4 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1995); cell refinement: RAPID-AUTO (Rigaku, 1995); data reduction: RAPID-AUTO (Rigaku, 1995); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

trans-Bis[8-(benzylsulfanyl)quinoline-κ²N,S]dichloridocobalt(II) top

Crystal data top

[CoCl₂(C₁₆H₁₃NS)₂]	F(000) = 650
M_r = 632.50	D_x = 1.512 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71075 Å
a = 8.00610 (17) Å	Cell parameters from 18593 reflections
b = 13.5141 (3) Å	θ = 2.2–27.5°
c = 13.3349 (3) Å	µ = 0.99 mm⁻¹
β = 105.714 (7)°	T = 103 K
V = 1388.85 (7) Å³	Prism, colourless
Z = 2	0.09 × 0.04 × 0.02 mm

Data collection top

Rigaku VariMax RAPID diffractometer	3191 independent reflections
Radiation source: rotating anode X-ray generator, MicroMax 007	2814 reflections with I > 2σ(I)
Multi-layer mirror optics monochromator	R_int = 0.034
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 2.6°
ω scans	h = −9→10
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	k = −17→17
T_min = 0.780, T_max = 1.000	l = −17→17
22957 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.031	H-atom parameters constrained
wR(F²) = 0.082	w = 1/[σ²(F_o²) + (0.0232P)² + 1.8429P] where P = (F_o² + 2F_c²)/3
S = 1.18	(Δ/σ)_max < 0.001
3191 reflections	Δρ_max = 0.44 e Å⁻³
178 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints

Special details top

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. H atoms were positioned geometrically and constrained to ride on their parent atoms with C—H and CH₂ bond distances of 0.95 and 0.99 Å. U_iso(H) values were set to 1.2 U_eq(C).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Co1	0.500000	0.500000	0.500000	0.01456 (10)
Cl1	0.75883 (6)	0.50541 (4)	0.64296 (4)	0.01844 (12)
S1	0.64306 (7)	0.43574 (4)	0.36942 (4)	0.01617 (12)
N1	0.5642 (2)	0.63898 (13)	0.44057 (13)	0.0157 (3)
C1	0.5280 (3)	0.72466 (16)	0.47761 (17)	0.0182 (4)
H1	0.479481	0.723445	0.535214	0.022*
C2	0.5564 (3)	0.81773 (16)	0.43738 (18)	0.0203 (4)
H2	0.527515	0.876968	0.467243	0.024*
C3	0.6260 (3)	0.82107 (16)	0.35484 (17)	0.0205 (4)
H3	0.646246	0.882891	0.326311	0.025*
C4	0.6677 (3)	0.73190 (16)	0.31209 (16)	0.0172 (4)
C5	0.7444 (3)	0.73145 (17)	0.22805 (17)	0.0211 (4)
H5	0.765834	0.792080	0.197652	0.025*
C6	0.7877 (3)	0.64363 (17)	0.19073 (17)	0.0227 (5)
H6	0.841301	0.643561	0.135286	0.027*
C7	0.7535 (3)	0.55343 (17)	0.23382 (17)	0.0219 (5)
H7	0.781298	0.492970	0.205753	0.026*
C8	0.6802 (3)	0.55136 (15)	0.31611 (16)	0.0173 (4)
C9	0.6357 (3)	0.64133 (15)	0.35748 (16)	0.0159 (4)
C10	0.8657 (3)	0.39310 (16)	0.42715 (18)	0.0196 (4)
H10A	0.936644	0.403595	0.377737	0.023*
H10B	0.918744	0.430657	0.491654	0.023*
C11	0.8590 (3)	0.28453 (16)	0.45155 (17)	0.0183 (4)
C12	0.8020 (3)	0.21507 (17)	0.37238 (19)	0.0231 (5)
H12	0.769255	0.235779	0.301657	0.028*
C13	0.7929 (3)	0.11537 (17)	0.3968 (2)	0.0271 (5)
H13	0.752454	0.068236	0.342799	0.033*
C14	0.8429 (3)	0.08496 (17)	0.4998 (2)	0.0280 (5)
H14	0.836682	0.016931	0.516390	0.034*
C15	0.9017 (3)	0.15333 (18)	0.5785 (2)	0.0277 (5)
H15	0.938461	0.132049	0.649012	0.033*
C16	0.9073 (3)	0.25348 (17)	0.55467 (19)	0.0230 (5)
H16	0.944155	0.300590	0.609058	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0166 (2)	0.01190 (19)	0.01521 (19)	−0.00096 (15)	0.00437 (15)	0.00003 (15)
Cl1	0.0184 (2)	0.0177 (2)	0.0182 (2)	−0.00075 (19)	0.00324 (19)	−0.00025 (19)
S1	0.0184 (2)	0.0127 (2)	0.0175 (2)	0.00018 (19)	0.00518 (19)	0.00035 (19)
N1	0.0154 (8)	0.0149 (8)	0.0161 (8)	−0.0004 (7)	0.0030 (7)	0.0004 (7)
C1	0.0182 (10)	0.0162 (10)	0.0196 (10)	−0.0017 (8)	0.0044 (8)	−0.0016 (8)
C2	0.0204 (10)	0.0139 (10)	0.0251 (11)	0.0007 (8)	0.0034 (9)	−0.0012 (8)
C3	0.0194 (10)	0.0151 (10)	0.0235 (11)	−0.0016 (8)	0.0001 (9)	0.0039 (8)
C4	0.0161 (10)	0.0166 (10)	0.0164 (10)	−0.0009 (8)	0.0001 (8)	0.0034 (8)
C5	0.0235 (11)	0.0207 (11)	0.0175 (10)	−0.0022 (9)	0.0028 (8)	0.0064 (8)
C6	0.0270 (11)	0.0242 (11)	0.0184 (11)	0.0002 (9)	0.0088 (9)	0.0045 (9)
C7	0.0262 (11)	0.0206 (11)	0.0203 (10)	0.0032 (9)	0.0084 (9)	0.0014 (9)
C8	0.0192 (10)	0.0161 (10)	0.0159 (10)	−0.0006 (8)	0.0035 (8)	0.0018 (8)
C9	0.0154 (9)	0.0151 (9)	0.0157 (10)	0.0000 (8)	0.0014 (8)	0.0020 (8)
C10	0.0168 (10)	0.0161 (10)	0.0260 (11)	−0.0003 (8)	0.0061 (9)	0.0018 (9)
C11	0.0151 (10)	0.0155 (10)	0.0255 (11)	0.0022 (8)	0.0075 (8)	0.0014 (8)
C12	0.0289 (12)	0.0191 (11)	0.0244 (11)	0.0021 (9)	0.0127 (9)	−0.0006 (9)
C13	0.0325 (13)	0.0173 (11)	0.0356 (13)	0.0002 (9)	0.0164 (11)	−0.0045 (10)
C14	0.0271 (12)	0.0156 (11)	0.0441 (15)	0.0024 (9)	0.0142 (11)	0.0061 (10)
C15	0.0226 (11)	0.0262 (12)	0.0321 (13)	0.0004 (10)	0.0038 (10)	0.0108 (10)
C16	0.0190 (10)	0.0216 (11)	0.0265 (12)	−0.0010 (9)	0.0032 (9)	0.0029 (9)

Geometric parameters (Å, º) top

Co1—Cl1ⁱ	2.4070 (5)	C6—C7	1.406 (3)
Co1—Cl1	2.4070 (5)	C7—H7	0.9500
Co1—S1	2.4856 (5)	C7—C8	1.378 (3)
Co1—S1ⁱ	2.4856 (5)	C9—C4	1.419 (3)
Co1—N1ⁱ	2.1542 (17)	C9—C8	1.420 (3)
Co1—N1	2.1543 (17)	C10—H10A	0.9900
S1—C8	1.775 (2)	C10—H10B	0.9900
S1—C10	1.832 (2)	C11—C10	1.507 (3)
N1—C1	1.322 (3)	C11—C12	1.394 (3)
N1—C9	1.378 (3)	C11—C16	1.389 (3)
C1—H1	0.9500	C12—H12	0.9500
C2—C1	1.410 (3)	C13—C12	1.393 (3)
C2—H2	0.9500	C13—H13	0.9500
C2—C3	1.362 (3)	C14—C13	1.385 (4)
C3—H3	0.9500	C14—H14	0.9500
C4—C3	1.411 (3)	C14—C15	1.382 (4)
C4—C5	1.417 (3)	C15—H15	0.9500
C5—H5	0.9500	C16—C15	1.394 (3)
C5—C6	1.367 (3)	C16—H16	0.9500
C6—H6	0.9500

Cl1ⁱ—Co1—Cl1	180.0	C5—C6—H6	119.8
Cl1—Co1—S1ⁱ	84.016 (17)	C5—C6—C7	120.5 (2)
Cl1—Co1—S1	95.984 (17)	C7—C6—H6	119.8
Cl1ⁱ—Co1—S1	84.015 (17)	C6—C7—H7	119.5
Cl1ⁱ—Co1—S1ⁱ	95.984 (17)	C8—C7—C6	121.0 (2)
S1ⁱ—Co1—S1	180.0	C8—C7—H7	119.5
N1—Co1—Cl1ⁱ	88.58 (5)	C7—C8—S1	119.38 (17)
N1ⁱ—Co1—Cl1ⁱ	91.42 (5)	C7—C8—C9	119.84 (19)
N1ⁱ—Co1—Cl1	88.58 (5)	C9—C8—S1	120.78 (16)
N1—Co1—Cl1	91.42 (5)	N1—C9—C4	121.66 (19)
N1—Co1—S1	81.12 (5)	N1—C9—C8	119.66 (18)
N1ⁱ—Co1—S1ⁱ	81.12 (5)	C4—C9—C8	118.68 (19)
N1ⁱ—Co1—S1	98.88 (5)	S1—C10—H10A	110.1
N1—Co1—S1ⁱ	98.88 (5)	S1—C10—H10B	110.1
N1ⁱ—Co1—N1	180.00 (9)	H10A—C10—H10B	108.4
C8—S1—Co1	97.58 (7)	C11—C10—S1	108.03 (15)
C8—S1—C10	101.30 (10)	C11—C10—H10A	110.1
C10—S1—Co1	113.32 (8)	C11—C10—H10B	110.1
C1—N1—Co1	121.86 (14)	C12—C11—C10	121.0 (2)
C1—N1—C9	117.47 (18)	C16—C11—C10	119.4 (2)
C9—N1—Co1	120.55 (13)	C16—C11—C12	119.5 (2)
N1—C1—H1	117.8	C11—C12—H12	119.9
N1—C1—C2	124.4 (2)	C13—C12—C11	120.1 (2)
C2—C1—H1	117.8	C13—C12—H12	119.9
C1—C2—H2	120.6	C12—C13—H13	120.0
C3—C2—C1	118.7 (2)	C14—C13—C12	120.0 (2)
C3—C2—H2	120.6	C14—C13—H13	120.0
C2—C3—H3	120.3	C13—C14—H14	119.9
C2—C3—C4	119.4 (2)	C15—C14—C13	120.2 (2)
C4—C3—H3	120.3	C15—C14—H14	119.9
C3—C4—C5	121.6 (2)	C14—C15—H15	120.0
C3—C4—C9	118.32 (19)	C14—C15—C16	120.1 (2)
C5—C4—C9	120.0 (2)	C16—C15—H15	120.0
C4—C5—H5	120.0	C11—C16—C15	120.1 (2)
C6—C5—C4	119.9 (2)	C11—C16—H16	119.9
C6—C5—H5	120.0	C15—C16—H16	119.9

Co1—S1—C8—C7	−177.06 (17)	C6—C7—C8—S1	−178.85 (18)
Co1—S1—C8—C9	3.13 (18)	C6—C7—C8—C9	1.0 (3)
Co1—S1—C10—C11	91.07 (15)	C8—S1—C10—C11	−165.48 (15)
Co1—N1—C1—C2	−175.63 (16)	C8—C9—C4—C3	−178.91 (19)
Co1—N1—C9—C4	175.41 (15)	C8—C9—C4—C5	−0.8 (3)
Co1—N1—C9—C8	−5.1 (3)	C9—N1—C1—C2	0.5 (3)
N1—C9—C4—C3	0.6 (3)	C9—C4—C3—C2	−0.2 (3)
N1—C9—C4—C5	178.78 (19)	C9—C4—C5—C6	0.0 (3)
N1—C9—C8—S1	0.5 (3)	C10—S1—C8—C7	67.23 (19)
N1—C9—C8—C7	−179.27 (19)	C10—S1—C8—C9	−112.57 (18)
C1—N1—C9—C4	−0.7 (3)	C10—C11—C12—C13	−178.5 (2)
C1—N1—C9—C8	178.79 (19)	C10—C11—C16—C15	180.0 (2)
C1—C2—C3—C4	−0.1 (3)	C11—C16—C15—C14	−2.1 (4)
C3—C2—C1—N1	−0.1 (3)	C12—C11—C10—S1	64.7 (2)
C3—C4—C5—C6	178.1 (2)	C12—C11—C16—C15	1.2 (3)
C4—C5—C6—C7	1.3 (3)	C13—C14—C15—C16	1.5 (4)
C4—C9—C8—S1	−179.91 (16)	C14—C13—C12—C11	−0.9 (4)
C4—C9—C8—C7	0.3 (3)	C15—C14—C13—C12	0.0 (4)
C5—C4—C3—C2	−178.3 (2)	C16—C11—C10—S1	−114.0 (2)
C5—C6—C7—C8	−1.8 (4)	C16—C11—C12—C13	0.3 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···Cg2ⁱⁱ	0.95	2.89	3.575 (2)	131

Symmetry code: (ii) −x, −y, −z.

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trans-Bis[8-(benzyl­sulfan­yl)quinoline-κ2N,S]di­chlorido­cobalt(II)

Supporting information

Key indicators

checkCIF/PLATON results

trans-Bis[8-(benzylsulfanyl)quinoline-κ²N,S]dichloridocobalt(II)