4-(Di­methyl­amino)­pyridinium trichlorido[4-(di­methyl­amino)­pyridine-κN]cobaltate(II)

Guenifa, F.; Hadjadj, N.; Zeghouan, O.; Bendjeddou, L.; Merazig, H.

doi:10.1107/S1600536813015602

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 7| July 2013| Pages m379-m380

https://doi.org/10.1107/S1600536813015602

Open

access

4-(Dimethylamino)pyridinium trichlorido[4-(dimethylamino)pyridine-κN]cobaltate(II)

Fatiha Guenifa,^a Nasreddine Hadjadj,^a Ouahida Zeghouan,^a Lamia Bendjeddou ^a ^* and Hocine Merazig ^a

^aUnité de Recherche Chimie de l'Environnement et Moléculaire Structurale, 'CHEMS', Faculté des Sciences Exactes, Campus Chaabet Ersas, Université Constantine I, 25000 Constantine, Algeria
^*Correspondence e-mail: Lamiabendjeddou@yahoo.fr

(Received 21 May 2013; accepted 4 June 2013; online 12 June 2013)

In the anion of the title compound, (C₇H₁₁N₂)[CoCl₃(C₇H₁₀N₂)], the Co^II ion is coordinated by one N atom from a 4-(dimethylamino)pyridine (DMAP) ligand and three Cl atoms, forming a CoNCl₃ polyhedron with a distorted tetrahedral geometry. In the crystal, cations and anions are linked via weak N—H⋯Cl and C—H⋯Cl hydrogen bonds. Double layers of complex anions stack along the b- axis direction, which alternate with double layers of 4-(dimethylamino)-pyridinium cations.

Related literature

For applications and properties of DMAP, see: Araki et al. (2005 ); Satgé et al. (2004 ). For Co—N and Co—Cl bond lengths and angles in related compounds, see: Akbarzadeh Torbati et al. (2010 ); Baker et al. (1988 ). For hysrogen-bond motifs, see: Bernstein et al. (1995 );

Experimental

Crystal data

(C₇H₁₁N₂)[CoCl₃(C₇H₁₀N₂)]
M_r = 410.63
Triclinic, $[P \overline 1]$
a = 7.7468 (2) Å
b = 8.4036 (2) Å
c = 15.4765 (4) Å
α = 79.732 (2)°
β = 89.983 (2)°
γ = 67.889 (2)°
V = 916.02 (4) Å³
Z = 2
Mo Kα radiation
μ = 1.38 mm⁻¹
T = 293 K
0.1 × 0.09 × 0.08 mm

Data collection

Bruker APEXII diffractometer
7932 measured reflections
3230 independent reflections
2982 reflections with I > 2σ(I)
R_int = 0.012

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.054
S = 1.04
3230 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Selected bond lengths (Å)

Co—Cl1	2.2482 (6)
Co—Cl2	2.2642 (5)
Co—Cl3	2.2680 (5)
Co—N2	2.0154 (14)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯Cl2ⁱ	0.86	2.64	3.3535 (17)	142
N4—H4⋯Cl3ⁱ	0.86	2.70	3.3279 (17)	131
C13—H13⋯Cl3ⁱ	0.93	2.81	3.4048 (19)	123
Symmetry code: (i) -x+2, -y, -z+1.

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012), Mercury (Macrae et al., 2006 ) and POVRay (Persistence of Vision Team, 2004 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813015602/vm2195sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813015602/vm2195Isup2.hkl

checkCIF report

Comment top

The N-heteroaromatic ligand 4-(dimethylamino) pyridine (DMAP) finds use as a homogeneous catalyst in cellulose acylation in the synthesis of biodegradable plastics (Satgé et al., 2004). DMAP is also known to form transition metal complexes which exhibit luminescence properties (Araki et al., 2005). We report here the synthesis and crystal structure of such a cobalt(II) complex with 4-(dimethylamino)pyridine.

The title compound (I) consists of one complex anion [CoCl₃(C₇H₁₀N₂)]^- and one 4-(dimethylamino)-pyridinium cation (Figure 1). In the structure of (I), each cobalt(II) is coordinated by one N atom from the DMAP ligand and three Cl atoms, forming a distorted tetrahedral coordination geometry. The Co—N and Co—Cl bond lengths and angles (Table 1) are within normal range as observed in: dichloro(6,6'-dimethyl-2,2'-bipyridyl)cobalt(II) hemibenzene solvate (Baker et al., 1988) and dichlorido(6,6'-dimethyl-2, 2'-bipyridine-κ²N,N')cobalt(II) (Akbarzadeh Torbati et al., 2010) .

The crystal structure of the title compound (I) is formed by double layers of complex anions [CoCl₃(C₇H₁₀N₂)]^- stacking along the b axis, at c = 0 and 1, which alternate with double layers of 4-(dimethylamino)-pyridinium cations placed along the [010] direction at c = 1/2 (Figure 2). The crystal packing is consolidated by two N—H···Cl and one C—H···Cl hydrogen bonds established between cations and anions, forming rings in two-dimensional network which can be described by the graph-set motif R¹₂(5) and R²₁ (4) (Bernstein et al., 1995) (Figure 3).

Related literature top

For applications and properties of DMAP, see: Araki et al. (2005); Satgé et al. (2004). For Co—N and Co—Cl bond lengths and angles in related compounds, see: Akbarzadeh Torbati et al. (2010); Baker et al. (1988). For hysrogen-bond motifs, see: Bernstein et al. (1995);

Experimental top

A mixture of NaN₃ and CoCl₂.6H₂O in methanol was stirred for half an hour, then 4-dimethylaminopyridine was added to the solution and the reaction continued to stir for one hour. After filtration, the pink filtrate was allowed to stand at room temperature. Blue crystals were obtained by slow evaporation.

Structure description top

For applications and properties of DMAP, see: Araki et al. (2005); Satgé et al. (2004). For Co—N and Co—Cl bond lengths and angles in related compounds, see: Akbarzadeh Torbati et al. (2010); Baker et al. (1988). For hysrogen-bond motifs, see: Bernstein et al. (1995);

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SIR2002 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012), Mercury (Macrae et al., 2006) and POVRay (Persistence of Vision Team, 2004).

Figures top

	Fig. 1. The asymmetric unit of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are represented as spheres of arbitrary radii.
	Fig. 2. View of the crystal structure of (I), showing the alternating double layers of cations and anions along the b axis.
	Fig. 3. Part of the crystal structure, showing the aggregation of R¹₂(5) and R²₁ (4) hydrogen-bonding motifs. [Symmetry codes: (ii) 1-x, 1-y, 1-z; (iii) -1+x, 1+y, z]

4-(Dimethylamino)pyridinium trichlorido[4-(dimethylamino)pyridine-κN]cobaltate(II) top

Crystal data top

(C₇H₁₁N₂)[CoCl₃(C₇H₁₀N₂)]	Z = 2
M_r = 410.63	F(000) = 422
Triclinic, P1	D_x = 1.489 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7468 (2) Å	Cell parameters from 3230 reflections
b = 8.4036 (2) Å	θ = 2.7–25.0°
c = 15.4765 (4) Å	µ = 1.38 mm⁻¹
α = 79.732 (2)°	T = 293 K
β = 89.983 (2)°	Prism, blue
γ = 67.889 (2)°	0.1 × 0.09 × 0.08 mm
V = 916.02 (4) Å³

Data collection top

Bruker APEXII diffractometer	2982 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.012
Graphite monochromator	θ_max = 25.0°, θ_min = 2.7°
φ scans	h = −9→9
7932 measured reflections	k = −9→9
3230 independent reflections	l = −18→18

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.021	w = 1/[σ²(F_o²) + (0.0266P)² + 0.4298P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.054	(Δ/σ)_max = 0.002
S = 1.04	Δρ_max = 0.31 e Å⁻³
3230 reflections	Δρ_min = −0.24 e Å⁻³
199 parameters

Crystal data top

(C₇H₁₁N₂)[CoCl₃(C₇H₁₀N₂)]	γ = 67.889 (2)°
M_r = 410.63	V = 916.02 (4) Å³
Triclinic, P1	Z = 2
a = 7.7468 (2) Å	Mo Kα radiation
b = 8.4036 (2) Å	µ = 1.38 mm⁻¹
c = 15.4765 (4) Å	T = 293 K
α = 79.732 (2)°	0.1 × 0.09 × 0.08 mm
β = 89.983 (2)°

Data collection top

Bruker APEXII diffractometer	2982 reflections with I > 2σ(I)
7932 measured reflections	R_int = 0.012
3230 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	0 restraints
wR(F²) = 0.054	H-atom parameters constrained
S = 1.04	Δρ_max = 0.31 e Å⁻³
3230 reflections	Δρ_min = −0.24 e Å⁻³
199 parameters

Special details top

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 esds are taken into account in the estimation of distances, angles and torsion angles

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
Co	0.97567 (3)	−0.05454 (3)	0.75509 (1)	0.0213 (1)
Cl1	1.17207 (6)	0.08718 (6)	0.73814 (3)	0.0306 (1)
Cl2	1.12085 (6)	−0.34664 (5)	0.80434 (3)	0.0341 (1)
Cl3	0.80521 (6)	−0.03086 (6)	0.63092 (3)	0.0309 (1)
N1	0.4028 (2)	0.28626 (19)	1.01267 (9)	0.0296 (4)
N2	0.78837 (18)	0.06985 (17)	0.83537 (9)	0.0226 (4)
C1	0.2121 (2)	0.2955 (3)	1.00244 (12)	0.0344 (5)
C2	0.4620 (3)	0.3238 (3)	1.09356 (12)	0.0404 (6)
C3	0.5268 (2)	0.2194 (2)	0.95499 (10)	0.0240 (5)
C4	0.4763 (2)	0.1638 (2)	0.88186 (10)	0.0247 (5)
C5	0.6070 (2)	0.0912 (2)	0.82633 (10)	0.0235 (5)
C6	0.8363 (2)	0.1278 (2)	0.90386 (11)	0.0261 (5)
C7	0.7166 (2)	0.1992 (2)	0.96373 (11)	0.0279 (5)
N3	0.5958 (2)	0.6338 (2)	0.60387 (10)	0.0348 (5)
N4	0.8714 (2)	0.4027 (2)	0.40501 (11)	0.0345 (5)
C8	0.4455 (3)	0.8064 (3)	0.58671 (16)	0.0464 (7)
C9	0.6493 (4)	0.5499 (4)	0.69593 (13)	0.0620 (9)
C10	0.6871 (2)	0.5610 (2)	0.53913 (11)	0.0242 (5)
C11	0.6388 (2)	0.6428 (2)	0.44901 (11)	0.0261 (5)
C12	0.7323 (3)	0.5605 (3)	0.38523 (11)	0.0318 (6)
C13	0.9237 (3)	0.3224 (2)	0.48886 (14)	0.0359 (6)
C14	0.8384 (2)	0.3958 (2)	0.55592 (12)	0.0309 (5)
H1A	0.14222	0.34572	1.04879	0.0515*
H1B	0.21388	0.17984	1.00525	0.0515*
H1C	0.15458	0.36701	0.94653	0.0515*
H2A	0.35548	0.37006	1.12652	0.0605*
H2B	0.51870	0.40810	1.07920	0.0605*
H2C	0.55093	0.21800	1.12820	0.0605*
H4A	0.35311	0.17666	0.87136	0.0296*
H5	0.56902	0.05397	0.77929	0.0281*
H6	0.95919	0.11843	0.91068	0.0313*
H7	0.75922	0.23461	1.01020	0.0334*
H4	0.92757	0.35268	0.36341	0.0414*
H8A	0.39712	0.83607	0.64133	0.0696*
H8B	0.34751	0.80547	0.54908	0.0696*
H8C	0.49274	0.89144	0.55842	0.0696*
H9A	0.56759	0.62160	0.73266	0.0929*
H9B	0.77569	0.53523	0.71003	0.0929*
H9C	0.63979	0.43749	0.70578	0.0929*
H11	0.54315	0.75273	0.43378	0.0313*
H12	0.69889	0.61485	0.32650	0.0382*
H13	1.02129	0.21331	0.50122	0.0430*
H14	0.87896	0.33776	0.61367	0.0371*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co	0.0182 (1)	0.0204 (1)	0.0238 (1)	−0.0059 (1)	0.0025 (1)	−0.0039 (1)
Cl1	0.0251 (2)	0.0346 (2)	0.0351 (2)	−0.0161 (2)	0.0011 (2)	−0.0038 (2)
Cl2	0.0423 (3)	0.0219 (2)	0.0288 (2)	−0.0039 (2)	0.0040 (2)	−0.0005 (2)
Cl3	0.0260 (2)	0.0317 (2)	0.0315 (2)	−0.0057 (2)	−0.0046 (2)	−0.0092 (2)
N1	0.0294 (8)	0.0294 (8)	0.0233 (7)	−0.0030 (6)	0.0043 (6)	−0.0069 (6)
N2	0.0194 (7)	0.0225 (7)	0.0245 (7)	−0.0061 (5)	0.0014 (5)	−0.0054 (5)
C1	0.0273 (9)	0.0329 (10)	0.0304 (9)	0.0003 (7)	0.0098 (7)	−0.0014 (8)
C2	0.0501 (12)	0.0379 (11)	0.0266 (9)	−0.0065 (9)	0.0054 (8)	−0.0130 (8)
C3	0.0259 (8)	0.0168 (8)	0.0229 (8)	−0.0021 (6)	0.0010 (7)	−0.0015 (6)
C4	0.0187 (8)	0.0278 (9)	0.0251 (8)	−0.0068 (7)	0.0005 (6)	−0.0037 (7)
C5	0.0225 (8)	0.0251 (8)	0.0223 (8)	−0.0084 (7)	−0.0003 (6)	−0.0050 (7)
C6	0.0207 (8)	0.0256 (9)	0.0312 (9)	−0.0080 (7)	−0.0019 (7)	−0.0055 (7)
C7	0.0289 (9)	0.0257 (9)	0.0279 (9)	−0.0081 (7)	−0.0038 (7)	−0.0077 (7)
N3	0.0380 (9)	0.0459 (9)	0.0282 (8)	−0.0206 (7)	0.0062 (7)	−0.0161 (7)
N4	0.0364 (8)	0.0359 (9)	0.0430 (9)	−0.0214 (7)	0.0158 (7)	−0.0202 (7)
C8	0.0357 (11)	0.0520 (13)	0.0636 (14)	−0.0192 (10)	0.0152 (10)	−0.0358 (11)
C9	0.0711 (17)	0.097 (2)	0.0253 (10)	−0.0384 (15)	0.0099 (10)	−0.0160 (12)
C10	0.0245 (8)	0.0268 (9)	0.0269 (8)	−0.0157 (7)	0.0010 (7)	−0.0063 (7)
C11	0.0248 (8)	0.0235 (8)	0.0301 (9)	−0.0107 (7)	−0.0021 (7)	−0.0022 (7)
C12	0.0394 (10)	0.0409 (11)	0.0248 (9)	−0.0269 (9)	0.0027 (8)	−0.0047 (8)
C13	0.0287 (9)	0.0245 (9)	0.0568 (12)	−0.0121 (7)	0.0048 (9)	−0.0093 (9)
C14	0.0323 (9)	0.0274 (9)	0.0330 (9)	−0.0153 (8)	−0.0053 (8)	0.0026 (7)

Geometric parameters (Å, º) top

Co—Cl1	2.2482 (6)	C2—H2C	0.9600
Co—Cl2	2.2642 (5)	C2—H2A	0.9600
Co—Cl3	2.2680 (5)	C2—H2B	0.9600
Co—N2	2.0154 (14)	C4—H4A	0.9300
N1—C1	1.457 (2)	C5—H5	0.9300
N1—C2	1.459 (2)	C6—H6	0.9300
N1—C3	1.344 (2)	C7—H7	0.9300
N2—C5	1.352 (2)	C10—C11	1.422 (2)
N2—C6	1.349 (2)	C10—C14	1.420 (2)
N3—C9	1.456 (3)	C11—C12	1.358 (3)
N3—C10	1.331 (2)	C13—C14	1.347 (3)
N3—C8	1.457 (3)	C8—H8A	0.9600
N4—C12	1.339 (3)	C8—H8B	0.9600
N4—C13	1.336 (3)	C8—H8C	0.9600
N4—H4	0.8600	C9—H9A	0.9600
C3—C7	1.419 (2)	C9—H9B	0.9600
C3—C4	1.407 (2)	C9—H9C	0.9600
C4—C5	1.363 (2)	C11—H11	0.9300
C6—C7	1.363 (2)	C12—H12	0.9300
C1—H1B	0.9600	C13—H13	0.9300
C1—H1A	0.9600	C14—H14	0.9300
C1—H1C	0.9600

Co···H4ⁱ	3.2300	C13···H8B^viii	2.8000
Cl1···N2	3.3714 (16)	C14···H9B	2.8000
Cl1···C4ⁱⁱ	3.5458 (17)	C14···H9C	2.7800
Cl1···C5ⁱⁱ	3.6498 (17)	H1A···H2A	2.1400
Cl1···C6	3.6194 (17)	H1A···Cl2^vii	3.0500
Cl1···C12ⁱⁱⁱ	3.549 (2)	H1B···C7^vii	2.9700
Cl2···N4ⁱ	3.3535 (17)	H1B···H4A	2.3400
Cl2···Cl3	3.5783 (7)	H1B···C4	2.7700
Cl3···N2	3.4083 (14)	H1B···C6^vii	2.8800
Cl3···Cl2	3.5783 (7)	H1B···N2^vii	2.9400
Cl3···C8^iv	3.648 (3)	H1B···C5^vii	3.0700
Cl3···C13ⁱ	3.4048 (19)	H1C···Cl2^xii	2.8900
Cl3···N4ⁱ	3.3279 (17)	H1C···C4	2.7400
Cl3···C5	3.5318 (16)	H1C···H4A	2.2600
Cl1···H5ⁱⁱ	3.0400	H2A···H1A	2.1400
Cl1···H14	2.8700	H2A···C9^xi	2.9400
Cl1···H12ⁱⁱⁱ	3.0400	H2A···H9A^xi	2.2800
Cl1···H4Aⁱⁱ	2.8500	H2B···H7	2.2900
Cl1···H8A^v	2.8400	H2B···C7	2.7800
Cl1···H6	3.1400	H2B···C3^xi	2.9600
Cl1···H2C^vi	3.0700	H2B···C7^xi	3.0600
Cl2···H1C^v	2.8900	H2B···Cl2^vi	3.1500
Cl2···H1A^vii	3.0500	H2C···Cl1^vi	3.0700
Cl2···H2B^vi	3.1500	H2C···C7	2.8500
Cl2···H4ⁱ	2.6400	H2C···H7	2.4600
Cl3···H8C^iv	3.0000	H4···Cl2ⁱ	2.6400
Cl3···H5	2.9500	H4···Coⁱ	3.2300
Cl3···H4ⁱ	2.7000	H4···Cl3ⁱ	2.7000
Cl3···H8B^viii	3.0300	H4A···Cl1^ix	2.8500
Cl3···H11^viii	2.8600	H4A···H1C	2.2600
Cl3···H13ⁱ	2.8100	H4A···H1B	2.3400
N2···Cl1	3.3714 (16)	H4A···C1	2.4900
N2···Cl3	3.4083 (14)	H5···Cl1^ix	3.0400
N4···C14ⁱⁱⁱ	3.394 (2)	H5···Cl3	2.9500
N4···Cl2ⁱ	3.3535 (17)	H6···Cl1	3.1400
N4···Cl3ⁱ	3.3279 (17)	H7···C2	2.5600
N2···H1B^vii	2.9400	H7···H2B	2.2900
N4···H8B^viii	2.8700	H7···H2C	2.4600
C4···Cl1^ix	3.5458 (17)	H8A···Cl1^xii	2.8400
C5···Cl1^ix	3.6498 (17)	H8A···H9A	2.0700
C8···Cl3^x	3.648 (3)	H8B···C11	2.7900
C10···C13ⁱⁱⁱ	3.509 (3)	H8B···H11	2.3400
C10···C11^viii	3.533 (2)	H8B···Cl3^viii	3.0300
C11···C10^viii	3.533 (2)	H8B···N4^viii	2.8700
C12···Cl1ⁱⁱⁱ	3.549 (2)	H8B···C13^viii	2.8000
C13···C10ⁱⁱⁱ	3.509 (3)	H8C···Cl3^x	3.0000
C13···Cl3ⁱ	3.4048 (19)	H8C···C11	2.8300
C13···C14ⁱⁱⁱ	3.491 (3)	H8C···H11	2.3900
C14···C13ⁱⁱⁱ	3.491 (3)	H8C···H8C^xiii	2.3600
C14···N4ⁱⁱⁱ	3.394 (2)	H9A···H8A	2.0700
C1···H4A	2.4900	H9A···C2^xi	2.8000
C2···H9A^xi	2.8000	H9A···H2A^xi	2.2800
C2···H7	2.5600	H9B···C14	2.8000
C3···H2B^xi	2.9600	H9B···H14	2.3500
C4···H1B	2.7700	H9C···C14	2.7800
C4···H1C	2.7400	H9C···H14	2.3300
C5···H1B^vii	3.0700	H11···C8	2.5500
C6···H1B^vii	2.8800	H11···H8B	2.3400
C7···H2B^xi	3.0600	H11···H8C	2.3900
C7···H2B	2.7800	H11···Cl3^viii	2.8600
C7···H2C	2.8500	H12···Cl1ⁱⁱⁱ	3.0400
C7···H1B^vii	2.9700	H13···Cl3ⁱ	2.8100
C8···H11	2.5500	H14···Cl1	2.8700
C9···H2A^xi	2.9400	H14···C9	2.5300
C9···H14	2.5300	H14···H9B	2.3500
C11···H8B	2.7900	H14···H9C	2.3300
C11···H8C	2.8300

Cl1—Co—Cl2	113.59 (2)	N1—C2—H2C	109.00
Cl1—Co—Cl3	115.11 (2)	C3—C4—H4A	120.00
Cl1—Co—N2	104.37 (4)	C5—C4—H4A	120.00
Cl2—Co—Cl3	104.29 (2)	N2—C5—H5	118.00
Cl2—Co—N2	114.18 (4)	C4—C5—H5	118.00
Cl3—Co—N2	105.29 (4)	C7—C6—H6	118.00
C1—N1—C2	118.24 (16)	N2—C6—H6	118.00
C1—N1—C3	119.92 (15)	C6—C7—H7	120.00
C2—N1—C3	121.09 (17)	C3—C7—H7	120.00
Co—N2—C5	121.29 (11)	C11—C10—C14	115.84 (15)
Co—N2—C6	122.80 (12)	N3—C10—C11	122.27 (15)
C5—N2—C6	115.81 (14)	N3—C10—C14	121.88 (16)
C9—N3—C10	121.60 (18)	C10—C11—C12	120.02 (16)
C8—N3—C9	116.52 (19)	N4—C12—C11	121.46 (16)
C8—N3—C10	121.76 (16)	N4—C13—C14	121.57 (17)
C12—N4—C13	120.55 (16)	C10—C14—C13	120.53 (17)
C13—N4—H4	120.00	N3—C8—H8A	109.00
C12—N4—H4	120.00	N3—C8—H8B	109.00
N1—C3—C4	121.87 (15)	N3—C8—H8C	109.00
C4—C3—C7	115.53 (14)	H8A—C8—H8B	109.00
N1—C3—C7	122.61 (15)	H8A—C8—H8C	109.00
C3—C4—C5	120.32 (15)	H8B—C8—H8C	109.00
N2—C5—C4	124.10 (15)	N3—C9—H9A	109.00
N2—C6—C7	124.37 (16)	N3—C9—H9B	109.00
C3—C7—C6	119.83 (15)	N3—C9—H9C	109.00
H1A—C1—H1B	109.00	H9A—C9—H9B	109.00
H1A—C1—H1C	109.00	H9A—C9—H9C	109.00
N1—C1—H1C	109.00	H9B—C9—H9C	109.00
N1—C1—H1A	109.00	C10—C11—H11	120.00
N1—C1—H1B	109.00	C12—C11—H11	120.00
H1B—C1—H1C	109.00	N4—C12—H12	119.00
H2B—C2—H2C	109.00	C11—C12—H12	119.00
N1—C2—H2B	109.00	N4—C13—H13	119.00
N1—C2—H2A	109.00	C14—C13—H13	119.00
H2A—C2—H2B	109.00	C10—C14—H14	120.00
H2A—C2—H2C	109.00	C13—C14—H14	120.00

Cl1—Co—N2—C5	144.99 (11)	C9—N3—C10—C14	1.6 (3)
Cl1—Co—N2—C6	−38.86 (13)	C8—N3—C10—C11	−2.9 (3)
Cl2—Co—N2—C5	−90.41 (12)	C12—N4—C13—C14	0.5 (3)
Cl2—Co—N2—C6	85.75 (13)	C13—N4—C12—C11	−0.8 (3)
Cl3—Co—N2—C5	23.37 (13)	C7—C3—C4—C5	1.9 (2)
Cl3—Co—N2—C6	−160.48 (12)	N1—C3—C4—C5	−177.79 (15)
C1—N1—C3—C4	2.7 (2)	N1—C3—C7—C6	178.90 (16)
C1—N1—C3—C7	−176.94 (16)	C4—C3—C7—C6	−0.8 (2)
C2—N1—C3—C4	172.62 (16)	C3—C4—C5—N2	−1.1 (2)
C2—N1—C3—C7	−7.0 (3)	N2—C6—C7—C3	−1.3 (3)
Co—N2—C5—C4	175.57 (12)	N3—C10—C11—C12	−177.82 (19)
C6—N2—C5—C4	−0.8 (2)	C14—C10—C11—C12	1.8 (3)
Co—N2—C6—C7	−174.29 (13)	N3—C10—C14—C13	177.53 (18)
C5—N2—C6—C7	2.1 (2)	C11—C10—C14—C13	−2.1 (3)
C8—N3—C10—C14	177.51 (18)	C10—C11—C12—N4	−0.4 (3)
C9—N3—C10—C11	−178.8 (2)	N4—C13—C14—C10	1.0 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···Cl2ⁱ	0.8600	2.6400	3.3535 (17)	142.00
N4—H4···Cl3ⁱ	0.8600	2.7000	3.3279 (17)	131.00
C13—H13···Cl3ⁱ	0.9300	2.8100	3.4048 (19)	123.00

Symmetry code: (i) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formula	(C₇H₁₁N₂)[CoCl₃(C₇H₁₀N₂)]
M_r	410.63
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.7468 (2), 8.4036 (2), 15.4765 (4)
α, β, γ (°)	79.732 (2), 89.983 (2), 67.889 (2)
V (Å³)	916.02 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.38
Crystal size (mm)	0.1 × 0.09 × 0.08

Data collection
Diffractometer	Bruker APEXII
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7932, 3230, 2982
R_int	0.012
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.054, 1.04
No. of reflections	3230
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.24

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SIR2002 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012), Mercury (Macrae et al., 2006) and POVRay (Persistence of Vision Team, 2004).

Selected bond lengths (Å) top

Co—Cl1	2.2482 (6)	Co—Cl3	2.2680 (5)
Co—Cl2	2.2642 (5)	Co—N2	2.0154 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···Cl2ⁱ	0.8600	2.6400	3.3535 (17)	142.00
N4—H4···Cl3ⁱ	0.8600	2.7000	3.3279 (17)	131.00
C13—H13···Cl3ⁱ	0.9300	2.8100	3.4048 (19)	123.00

Symmetry code: (i) −x+2, −y, −z+1.

Acknowledgements

This work was supported by the Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Université de Constantine 1, Algeria. Thanks are due to MESRS and ATRST (Ministère de l'Enseignement Supérieur et de la Recherche Scientifique et l'Agence Thématique de Recherche en Sciences et Technologie, Algeria) via the PNR program for financial support.

References

Akbarzadeh Torbati, N., Rezvani, A. R., Safari, N., Amani, V. & Khavasi, H. R. (2010). Acta Cryst. E66, m1236. Web of Science CSD CrossRef IUCr Journals Google Scholar
Araki, H., Tsuge, K., Sasaki, Y., Ishizaka, S. & Kitamura, N. (2005). Inorg. Chem. 44, 9667–9675. Web of Science CSD CrossRef PubMed CAS Google Scholar
Baker, G. L., Fronczek, F. R., Kiefer, G. E., Marston, C. R., Modenbach, C. L., Newkome, G. R., Puckett, W. E. & Watkins, S. F. (1988). Acta Cryst. C44, 1668–1669. CSD CrossRef CAS IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Persistence of Vision Team (2004). POV-RAY. Persistence of Vision Raytracer Pty Ltd, Victoria, Australia. URL: http://www.povray.org/. Google Scholar
Satgé, C., Granet, R., Verneuil, B., Branland, P. & Krausz, P. (2004). C. R. Chim. 7, 135–142. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 7| July 2013| Pages m379-m380

https://doi.org/10.1107/S1600536813015602

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

4-(Di­methyl­amino)­pyridinium tri­chlorido[4-(di­methyl­amino)­pyridine-κN]cobaltate(II)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

4-(Dimethylamino)pyridinium trichlorido[4-(dimethylamino)pyridine-κN]cobaltate(II)