Bis[N,N-dimethyl-1-(10H-pyrido[3,2-b][1,4]benzothia­zin-10-yl)propan-2-aminium] tetrakis­(thio­cyanato-κN)cobaltate(II)

Arunkashi, H.K.; Jeyaseelan, S.; Vepuri, S.B.; Revanasiddappa, H.D.; Devarajegowda, H.C.

doi:10.1107/S1600536810021367

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Pages m772-m773

doi:10.1107/S1600536810021367

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Bis[N,N-dimethyl-1-(10H-pyrido[3,2-b][1,4]benzothiazin-10-yl)propan-2-aminium] tetrakis(thiocyanato-κN)cobaltate(II)

H. K. Arunkashi,^a S. Jeyaseelan,^a Suresh Babu Vepuri,^b H. D. Revanasiddappa ^c and H. C. Devarajegowda ^a ^*

^aDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, ^bGITAM Institute of Pharmacy, GITAM University, Visakhapatnam 530 045, Andhrapradesh, India, and ^cDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, Karnataka, India
^*Correspondence e-mail: devarajegowda@yahoo.com

(Received 22 May 2010; accepted 4 June 2010; online 16 June 2010)

The asymmetric unit of the title salt, (C₁₆H₂₀N₃S)₂[Co(NCS)₄], comprises one monovalent isothiopendylium cation and one-half of a divalent thiocyanatocobaltate(II) anion (2 symmetry). The central thiazine ring of the cation is slightly twisted in a boat-like fashion, with r.m.s. deviations from the mean plane of 0.272 (1) and 0.2852 (8) Å for the N and S atoms. The molecular structure of the cation is stabilized by an intramolecular N—H⋯N hydrogen bond. Within the complex anion, the Co^II atom is tetrahedrally surrounded by four N atoms of the thiocyanate ligands. π–π stacking, with a distance of 3.7615 (10) Å between the centroids of benzene and pyridine rings, helps to consolidate the packing.

Related literature

For general background to isothipendyl, cobalt(II) and thiocyanate compounds, see: Kinnamon et al. (1994 ); Moreau et al. (1995 ); Scott et al. (1990 ); Hudson et al. (2005 ). For a related structure, see: Shi et al. (2005 ).

Experimental

Crystal data

(C₁₆H₂₀N₃S)₂[Co(NCS)₄]
M_r = 864.07
Monoclinic, C 2/c
a = 25.2420 (4) Å
b = 11.4357 (2) Å
c = 14.5939 (2) Å
β = 98.557 (1)°
V = 4165.78 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.75 mm⁻¹
T = 295 K
0.22 × 0.15 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: ψ scan (SADABS; Sheldrick, 2004 ) T_min = 0.852, T_max = 0.915
48347 measured reflections
6498 independent reflections
4566 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.114
S = 1.01
6498 reflections
243 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Co1—N4	1.9411 (19)
Co1—N5	1.9626 (16)

N4ⁱ—Co1—N4	113.17 (13)
N4—Co1—N5	108.95 (7)
N4—Co1—N5ⁱ	110.33 (8)
N5—Co1—N5ⁱ	104.78 (9)
Symmetry code: (i) $[-x, y, -z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N1	0.91	1.91	2.7494 (18)	152

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810021367/wm2356sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810021367/wm2356Isup2.hkl

checkCIF report

Comment top

The molecular structure of isothipendyl, C₁₆H₁₉N₃S, is close to that of phenothiazines. Isothipendyl is an antihistamine used in the treatment of allergies. It was also found to be active against parasites causing filariasis (Kinnamon et al., 1994). Photobiological properties of isothipendyl were also investigated and found to have ultraviolet B (UVB) protective activity (Moreau et al., 1995). Studies also suggest that cobalt and thiocyanates play some role in phototoxicity and in the development of conjugates for photoimmunotherapy (Scott et al., 1990; Hudson et al., 2005). These outcomes arouse our interest and we prepared the title salt [(C₁₆H₂₀N₃S)₂{Co(NCS)₄}], (I), for structural characterisation.

In the structure of (I), the Co atom of the anion is situated on a twofold rotation axis and is coordinated by four N atoms from four thiocyanate groups in a slightly distorted tetrahedral geometry (Fig. 1, Table 1). The bond lengths and bond angles of the cobaltate(II) anion are in good agreement with related structures (Shi et al., 2005).

Within the cation the dihedral angles between the benzene and the thiazine rings and between the pyridine and the thiazine rings are 15.73 (8)° and 14.77 (8)°, respectively. The central thiazine ring is slightly twisted as boat like. The deviation of the N and S atoms from the mean plane of the thiazine ring was found to be 0.272 (1) and 0.2852 (8) Å, respectively. The structure displays an intramolecular hydrogen bonding interaction between N3–H3A···N1 (Fig. 2 & Table 2).

There are significant π—π stacking interactions between the pyridine and benzene rings; the relevant distances are Cg2—Cg3ⁱ = 3.7615 (10) Å and Cg2—3ⁱ_perp = 3.6975 (7) Å, and Cg3—Cg2ⁱⁱ = 3.7614 (10) Å and Cg3—2ⁱⁱ_perp = 3.6820 (7) Å [symmetry codes: (i) 1/2 - x,1/2 + y,3/2 - z;(ii) 1/2 - x, -1/2 + y,3/2 - z; Cg2 and Cg3 are the centroids of the N1/C2–C6 and C7–C12 rings, respectively; CgI—J_perp is the perpendicular distance from CgI to ring J]. In addition, there are weak intermolecular C2—H2···S2 and C16—H16A···S2 interactions with H···S distances of 2.886 (10) and 2.919 (10) Å and D—H···A angles of 154.54 (12)° and 138.40 (14)°, respectively.

In the crystal structure, molecules stack along [010] (Fig. 3).

Related literature top

For general background to isothipendyl, cobalt(II) and thiocyanate compounds, see: Kinnamon et al. (1994); Moreau et al. (1995); Scott et al. (1990); Hudson et al. (2005). For a related structure, see: Shi et al. (2005).

Experimental top

The cobalt(II) salt was prepared by a single step method. Isothipendyl in ethanol (5 mmol) was slowly mixed with an ethanolic solution (5 mmol) of Co(SCN)₂^.2H₂O. The mixture was kept at room temperature for 30 min and warmed on a water bath (343–353 K) for 1 h. Green crystals suitable for X-ray diffraction were obtained by slow evaporation of the solvent (M.P. 453 K; Yield 79%).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Symmetry code a) -x, y, -z+1/2.
	Fig. 2. Packing of the molecules as viewed down [010].

Bis[N,N-dimethyl-1-(10H-pyrido[3,2- b][1,4]benzothiazin-10-yl)propan-2-aminium] tetrakis(thiocyanato-κN)cobaltate(II) top

Crystal data top

(C₁₆H₂₀N₃S)₂[Co(NCS)₄]	F(000) = 1796
M_r = 864.07	D_x = 1.378 Mg m⁻³
Monoclinic, C2/c	Melting point: 453 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 25.2420 (4) Å	Cell parameters from 6498 reflections
b = 11.4357 (2) Å	θ = 1.6–30.8°
c = 14.5939 (2) Å	µ = 0.75 mm⁻¹
β = 98.557 (1)°	T = 295 K
V = 4165.78 (11) Å³	Plate, green
Z = 4	0.22 × 0.15 × 0.12 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	6498 independent reflections
Radiation source: fine-focus sealed tube	4566 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω and ϕ scans	θ_max = 30.8°, θ_min = 1.6°
Absorption correction: ψ scan (SADABS; Sheldrick, 2004)	h = −36→36
T_min = 0.852, T_max = 0.915	k = −16→16
48347 measured reflections	l = −20→20

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0516P)² + 2.3179P] where P = (F_o² + 2F_c²)/3
6498 reflections	(Δ/σ)_max < 0.001
243 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

(C₁₆H₂₀N₃S)₂[Co(NCS)₄]	V = 4165.78 (11) Å³
M_r = 864.07	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 25.2420 (4) Å	µ = 0.75 mm⁻¹
b = 11.4357 (2) Å	T = 295 K
c = 14.5939 (2) Å	0.22 × 0.15 × 0.12 mm
β = 98.557 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	6498 independent reflections
Absorption correction: ψ scan (SADABS; Sheldrick, 2004)	4566 reflections with I > 2σ(I)
T_min = 0.852, T_max = 0.915	R_int = 0.032
48347 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.01	Δρ_max = 0.30 e Å⁻³
6498 reflections	Δρ_min = −0.37 e Å⁻³
243 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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 (Å²) top

	x	y	z	U_iso*/U_eq
Co1	0.0000	0.18800 (3)	0.2500	0.05395 (11)
S1	0.169598 (17)	0.36282 (5)	0.31347 (4)	0.06906 (15)
S2	0.09133 (3)	0.39599 (6)	0.04513 (5)	0.0913 (2)
S3	−0.09097 (2)	−0.11877 (5)	0.08464 (4)	0.06810 (15)
N1	0.30192 (5)	0.17216 (12)	0.37667 (10)	0.0479 (3)
N2	0.29026 (5)	0.36667 (11)	0.33141 (9)	0.0428 (3)
N3	0.40850 (5)	0.23282 (13)	0.40260 (9)	0.0503 (3)
H3A	0.3781	0.1888	0.3953	0.060*
N4	0.04020 (8)	0.28147 (18)	0.17318 (14)	0.0771 (5)
N5	−0.04823 (6)	0.08326 (15)	0.17017 (11)	0.0595 (4)
C2	0.28169 (8)	0.06803 (16)	0.39813 (13)	0.0589 (4)
H2	0.3049	0.0049	0.4101	0.071*
C3	0.22864 (9)	0.05145 (18)	0.40307 (14)	0.0663 (5)
H3	0.2161	−0.0205	0.4204	0.080*
C4	0.19412 (7)	0.14419 (19)	0.38174 (14)	0.0621 (5)
H4	0.1578	0.1352	0.3848	0.074*
C5	0.21316 (6)	0.24990 (16)	0.35591 (11)	0.0487 (4)
C6	0.26864 (5)	0.26126 (14)	0.35550 (10)	0.0413 (3)
C7	0.21115 (6)	0.48282 (17)	0.34832 (11)	0.0506 (4)
C8	0.18804 (8)	0.5880 (2)	0.36902 (13)	0.0653 (5)
H8	0.1513	0.5917	0.3700	0.078*
C9	0.21887 (10)	0.6863 (2)	0.38804 (14)	0.0729 (6)
H9	0.2030	0.7567	0.4007	0.087*
C10	0.27306 (10)	0.68031 (18)	0.38826 (14)	0.0693 (5)
H10	0.2939	0.7472	0.4000	0.083*
C11	0.29708 (8)	0.57504 (16)	0.37113 (12)	0.0562 (4)
H11	0.3341	0.5715	0.3736	0.067*
C12	0.26658 (6)	0.47499 (14)	0.35030 (10)	0.0443 (3)
C13	0.34445 (6)	0.36661 (15)	0.30759 (10)	0.0440 (3)
H13A	0.3491	0.4375	0.2732	0.053*
H13B	0.3476	0.3011	0.2666	0.053*
C14	0.39047 (6)	0.35898 (15)	0.38957 (11)	0.0459 (3)
H14	0.3763	0.3831	0.4456	0.055*
C15	0.43718 (7)	0.4390 (2)	0.37864 (16)	0.0689 (5)
H15A	0.4659	0.4254	0.4285	0.103*
H15B	0.4258	0.5190	0.3799	0.103*
H15C	0.4494	0.4230	0.3206	0.103*
C16	0.43609 (9)	0.2099 (2)	0.49819 (14)	0.0752 (6)
H16A	0.4490	0.1308	0.5024	0.113*
H16B	0.4114	0.2211	0.5414	0.113*
H16C	0.4657	0.2628	0.5125	0.113*
C17	0.44122 (9)	0.1896 (2)	0.33280 (17)	0.0764 (6)
H17A	0.4771	0.2191	0.3474	0.115*
H17B	0.4258	0.2162	0.2723	0.115*
H17C	0.4419	0.1057	0.3337	0.115*
C18	0.06195 (8)	0.32922 (17)	0.12044 (15)	0.0622 (5)
C19	−0.06629 (6)	−0.00127 (16)	0.13474 (12)	0.0492 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.04465 (17)	0.0540 (2)	0.0604 (2)	0.000	−0.00135 (13)	0.000
S1	0.03187 (19)	0.0899 (4)	0.0813 (3)	0.0035 (2)	−0.00519 (19)	0.0002 (3)
S2	0.0961 (5)	0.0837 (4)	0.0981 (5)	−0.0315 (4)	0.0272 (4)	0.0016 (3)
S3	0.0596 (3)	0.0733 (3)	0.0717 (3)	−0.0168 (2)	0.0107 (2)	−0.0148 (2)
N1	0.0407 (6)	0.0498 (7)	0.0536 (7)	−0.0035 (5)	0.0078 (5)	0.0019 (6)
N2	0.0304 (5)	0.0487 (7)	0.0503 (7)	−0.0008 (5)	0.0087 (5)	0.0030 (6)
N3	0.0354 (6)	0.0617 (8)	0.0528 (7)	0.0017 (6)	0.0038 (5)	−0.0058 (6)
N4	0.0690 (11)	0.0815 (12)	0.0766 (11)	−0.0245 (9)	−0.0027 (9)	0.0100 (10)
N5	0.0439 (7)	0.0615 (9)	0.0701 (9)	−0.0001 (7)	−0.0014 (6)	−0.0029 (8)
C2	0.0628 (10)	0.0498 (9)	0.0644 (10)	−0.0054 (8)	0.0108 (8)	0.0037 (8)
C3	0.0728 (12)	0.0586 (11)	0.0709 (12)	−0.0233 (10)	0.0218 (10)	−0.0009 (9)
C4	0.0458 (8)	0.0757 (12)	0.0674 (11)	−0.0228 (9)	0.0172 (8)	−0.0099 (10)
C5	0.0332 (6)	0.0644 (10)	0.0484 (8)	−0.0073 (7)	0.0055 (6)	−0.0045 (7)
C6	0.0326 (6)	0.0525 (8)	0.0389 (7)	−0.0047 (6)	0.0054 (5)	−0.0021 (6)
C7	0.0433 (7)	0.0657 (10)	0.0418 (7)	0.0115 (7)	0.0031 (6)	0.0061 (7)
C8	0.0597 (10)	0.0838 (14)	0.0521 (9)	0.0296 (10)	0.0071 (8)	0.0072 (9)
C9	0.0941 (16)	0.0655 (13)	0.0572 (11)	0.0290 (12)	0.0056 (10)	0.0009 (9)
C10	0.0937 (16)	0.0514 (10)	0.0614 (11)	0.0053 (10)	0.0066 (10)	0.0023 (9)
C11	0.0585 (10)	0.0530 (10)	0.0565 (9)	−0.0007 (8)	0.0066 (8)	0.0047 (8)
C12	0.0431 (7)	0.0520 (9)	0.0375 (7)	0.0056 (6)	0.0046 (5)	0.0057 (6)
C13	0.0340 (6)	0.0550 (9)	0.0448 (7)	−0.0025 (6)	0.0115 (5)	0.0029 (6)
C14	0.0322 (6)	0.0567 (9)	0.0495 (8)	−0.0044 (6)	0.0085 (6)	−0.0045 (7)
C15	0.0421 (8)	0.0783 (13)	0.0871 (14)	−0.0189 (9)	0.0116 (9)	−0.0023 (11)
C16	0.0714 (13)	0.0858 (15)	0.0613 (11)	0.0179 (11)	−0.0133 (10)	−0.0035 (10)
C17	0.0584 (11)	0.0925 (16)	0.0811 (14)	0.0187 (11)	0.0194 (10)	−0.0162 (12)
C18	0.0510 (9)	0.0556 (10)	0.0757 (12)	−0.0121 (8)	−0.0049 (9)	−0.0033 (9)
C19	0.0310 (6)	0.0614 (10)	0.0546 (9)	0.0033 (6)	0.0048 (6)	0.0030 (8)

Geometric parameters (Å, º) top

Co1—N4ⁱ	1.9411 (19)	C5—C6	1.4073 (19)
Co1—N4	1.9411 (19)	C7—C8	1.389 (3)
Co1—N5	1.9626 (16)	C7—C12	1.398 (2)
Co1—N5ⁱ	1.9626 (16)	C8—C9	1.372 (3)
S1—C5	1.7485 (18)	C8—H8	0.9300
S1—C7	1.756 (2)	C9—C10	1.369 (3)
S2—C18	1.607 (2)	C9—H9	0.9300
S3—C19	1.6102 (19)	C10—C11	1.387 (3)
N1—C6	1.328 (2)	C10—H10	0.9300
N1—C2	1.351 (2)	C11—C12	1.387 (2)
N2—C6	1.390 (2)	C11—H11	0.9300
N2—C12	1.420 (2)	C13—C14	1.541 (2)
N2—C13	1.4608 (18)	C13—H13A	0.9700
N3—C16	1.487 (2)	C13—H13B	0.9700
N3—C17	1.488 (2)	C14—C15	1.519 (2)
N3—C14	1.516 (2)	C14—H14	0.9800
N3—H3A	0.9100	C15—H15A	0.9600
N4—C18	1.148 (3)	C15—H15B	0.9600
N5—C19	1.157 (2)	C15—H15C	0.9600
C2—C3	1.365 (3)	C16—H16A	0.9600
C2—H2	0.9300	C16—H16B	0.9600
C3—C4	1.378 (3)	C16—H16C	0.9600
C3—H3	0.9300	C17—H17A	0.9600
C4—C5	1.374 (3)	C17—H17B	0.9600
C4—H4	0.9300	C17—H17C	0.9600

N4ⁱ—Co1—N4	113.17 (13)	C8—C9—H9	120.1
N4ⁱ—Co1—N5	110.33 (8)	C9—C10—C11	120.4 (2)
N4—Co1—N5	108.95 (7)	C9—C10—H10	119.8
N4ⁱ—Co1—N5ⁱ	108.95 (7)	C11—C10—H10	119.8
N4—Co1—N5ⁱ	110.33 (8)	C10—C11—C12	120.80 (19)
N5—Co1—N5ⁱ	104.78 (9)	C10—C11—H11	119.6
C5—S1—C7	99.06 (7)	C12—C11—H11	119.6
C6—N1—C2	118.85 (14)	C11—C12—C7	118.22 (16)
C6—N2—C12	121.00 (12)	C11—C12—N2	121.74 (14)
C6—N2—C13	118.47 (12)	C7—C12—N2	120.05 (15)
C12—N2—C13	118.87 (13)	N2—C13—C14	116.08 (12)
C16—N3—C17	110.70 (16)	N2—C13—H13A	108.3
C16—N3—C14	112.07 (14)	C14—C13—H13A	108.3
C17—N3—C14	114.63 (15)	N2—C13—H13B	108.3
C16—N3—H3A	106.3	C14—C13—H13B	108.3
C17—N3—H3A	106.3	H13A—C13—H13B	107.4
C14—N3—H3A	106.3	N3—C14—C15	111.28 (14)
C18—N4—Co1	172.97 (18)	N3—C14—C13	109.19 (13)
C19—N5—Co1	160.60 (14)	C15—C14—C13	113.05 (14)
N1—C2—C3	122.85 (19)	N3—C14—H14	107.7
N1—C2—H2	118.6	C15—C14—H14	107.7
C3—C2—H2	118.6	C13—C14—H14	107.7
C2—C3—C4	118.25 (18)	C14—C15—H15A	109.5
C2—C3—H3	120.9	C14—C15—H15B	109.5
C4—C3—H3	120.9	H15A—C15—H15B	109.5
C5—C4—C3	120.25 (16)	C14—C15—H15C	109.5
C5—C4—H4	119.9	H15A—C15—H15C	109.5
C3—C4—H4	119.9	H15B—C15—H15C	109.5
C4—C5—C6	118.11 (17)	N3—C16—H16A	109.5
C4—C5—S1	121.32 (13)	N3—C16—H16B	109.5
C6—C5—S1	120.26 (13)	H16A—C16—H16B	109.5
N1—C6—N2	117.76 (12)	N3—C16—H16C	109.5
N1—C6—C5	121.59 (15)	H16A—C16—H16C	109.5
N2—C6—C5	120.64 (14)	H16B—C16—H16C	109.5
C8—C7—C12	120.16 (18)	N3—C17—H17A	109.5
C8—C7—S1	119.17 (14)	N3—C17—H17B	109.5
C12—C7—S1	120.58 (13)	H17A—C17—H17B	109.5
C9—C8—C7	120.63 (19)	N3—C17—H17C	109.5
C9—C8—H8	119.7	H17A—C17—H17C	109.5
C7—C8—H8	119.7	H17B—C17—H17C	109.5
C10—C9—C8	119.72 (19)	N4—C18—S2	178.86 (19)
C10—C9—H9	120.1	N5—C19—S3	179.38 (17)

N4ⁱ—Co1—N5—C19	−126.5 (5)	S1—C7—C8—C9	−173.88 (15)
N4—Co1—N5—C19	108.7 (5)	C7—C8—C9—C10	−1.2 (3)
N5ⁱ—Co1—N5—C19	−9.4 (4)	C8—C9—C10—C11	−1.2 (3)
C6—N1—C2—C3	−3.0 (3)	C9—C10—C11—C12	2.3 (3)
N1—C2—C3—C4	2.5 (3)	C10—C11—C12—C7	−0.9 (3)
C2—C3—C4—C5	0.3 (3)	C10—C11—C12—N2	179.22 (16)
C3—C4—C5—C6	−2.4 (3)	C8—C7—C12—C11	−1.5 (2)
C3—C4—C5—S1	171.23 (15)	S1—C7—C12—C11	174.88 (12)
C7—S1—C5—C4	151.93 (15)	C8—C7—C12—N2	178.41 (14)
C7—S1—C5—C6	−34.59 (15)	S1—C7—C12—N2	−5.2 (2)
C2—N1—C6—N2	−178.41 (15)	C6—N2—C12—C11	147.52 (15)
C2—N1—C6—C5	0.7 (2)	C13—N2—C12—C11	−17.5 (2)
C12—N2—C6—N1	−149.64 (14)	C6—N2—C12—C7	−32.4 (2)
C13—N2—C6—N1	15.5 (2)	C13—N2—C12—C7	162.56 (14)
C12—N2—C6—C5	31.2 (2)	C6—N2—C13—C14	−77.11 (18)
C13—N2—C6—C5	−163.65 (14)	C12—N2—C13—C14	88.31 (17)
C4—C5—C6—N1	1.9 (2)	C16—N3—C14—C15	77.02 (19)
S1—C5—C6—N1	−171.75 (12)	C17—N3—C14—C15	−50.2 (2)
C4—C5—C6—N2	−178.98 (15)	C16—N3—C14—C13	−157.49 (15)
S1—C5—C6—N2	7.3 (2)	C17—N3—C14—C13	75.24 (17)
C5—S1—C7—C8	−150.12 (14)	N2—C13—C14—N3	96.79 (16)
C5—S1—C7—C12	33.45 (14)	N2—C13—C14—C15	−138.75 (16)
C12—C7—C8—C9	2.6 (3)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N1	0.91	1.91	2.7494 (18)	152

Experimental details

Crystal data
Chemical formula	(C₁₆H₂₀N₃S)₂[Co(NCS)₄]
M_r	864.07
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	295
a, b, c (Å)	25.2420 (4), 11.4357 (2), 14.5939 (2)
β (°)	98.557 (1)
V (Å³)	4165.78 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.75
Crystal size (mm)	0.22 × 0.15 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	ψ scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.852, 0.915
No. of measured, independent and observed [I > 2σ(I)] reflections	48347, 6498, 4566
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.720

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.114, 1.01
No. of reflections	6498
No. of parameters	243
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.37

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Selected geometric parameters (Å, º) top

Co1—N4	1.9411 (19)	Co1—N5	1.9626 (16)

N4ⁱ—Co1—N4	113.17 (13)	N4—Co1—N5ⁱ	110.33 (8)
N4—Co1—N5	108.95 (7)	N5—Co1—N5ⁱ	104.78 (9)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N1	0.91	1.9100	2.7494 (18)	152.00

Acknowledgements

The authors thank the DST India (FIST programme) for the use of the diffractometer at the School of Chemistry, Bharathidasan University, Tiruchirappalli, Tamil Nadu, India. They also thank Professor P. Thomas Muthiah for the data collection.

References

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hudson, R., Carcenac, M., Smith, K., Madden, L., Clarke, O. J., Pèlegrin, A., Greenman, J. & Boyle, R. W. (2005). Br. J. Cancer, 92, 1442–1449. Web of Science CrossRef PubMed CAS Google Scholar
Shi, J. M., Zhang, F. X., Lu, J. J. & Liu, L. D. (2005). Acta Cryst. E61, m1181–m1182. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kinnamon, K. E., Klayman, D. L., Poon, B. T., McCall, J. W., Dzimianski, M. T. & Rowan, S. J. (1994). Am. J. Trop. Med. Hyg. 51, 791–796. CAS PubMed Web of Science Google Scholar
Moreau, A., Dompmartin, A., Dubreuil, A. & Leroy, D. (1995). Photodermatol. Photoimmunol. Photomed. 11, 50–54. CrossRef CAS PubMed Web of Science Google Scholar
Scott, J., Quirke, J. M., Vreman, H. J., Stevenson, D. K. & Downum, K. R. (1990). J. Photochem. Photobiol. B, 7, 149–157. CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 66| Part 7| July 2010| Pages m772-m773

doi:10.1107/S1600536810021367

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bis[N,N-di­methyl-1-(10H-pyrido[3,2-b][1,4]benzo­thia­zin-10-yl)propan-2-aminium] tetra­kis­­(thio­cyanato-κN)cobaltate(II)

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Supporting information

Acknowledgements

References

metal-organic compounds

Bis[N,N-dimethyl-1-(10H-pyrido[3,2-b][1,4]benzothiazin-10-yl)propan-2-aminium] tetrakis(thiocyanato-κN)cobaltate(II)