Di­chlorido­(pyridine-κN)[2,3,5,6-tetra­kis­(pyridin-2-yl)pyrazine-κ³N²,N¹,N⁶]nickel(II)

In the title complex, [NiCl₂(C₅H₅N)(C₂₄H₁₆N₆)], the Ni^II ion is six-coordinated in a distorted octa­hedral coordination environment defined by three N atoms of the tridentate 2,3,5,6-tetra-2-pyridyl­pyrazine ligand, one N atom of the pyridine ligand and two Cl⁻ anions, with the latter being mutually trans. The complex is disposed about a twofold rotation axis along the a axis. The complex molecules are connected in the crystal via C—H...Cl, C—H...N and π–π [closest inter-centroid separation = 3.7446 (14) Å between pyridyl rings].

Key indicators

• Single-crystal X-ray study
• T = 223 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.024
• wR factor = 0.054
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C NonSolvent   Resd 1  C   Ueq(max)/Ueq(min) Range        3.6 Ratio

Alert level G
PLAT794_ALERT_5_G Tentative Bond Valency for Ni1       (II)      .       2.12 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         10 Info

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

   0 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL (Sheldrick, 2015b).

Dichlorido(pyridine-κN)[2,3,5,6-tetrakis(pyridin-2-yl)pyrazine-κ³N²,N¹,N⁶]nickel(II)

Crystal data

[NiCl2(C5H5N)(C24H16N6)]	Dx = 1.504 Mg m^−3
Mr = 597.14	Mo Kα radiation, λ = 0.71073 Å
Hexagonal, P6122	Cell parameters from 9199 reflections
a = 13.8244 (4) Å	θ = 2.4–26.0°
c = 23.8935 (8) Å	µ = 0.97 mm^−1
V = 3954.6 (3) Å^3	T = 223 K
Z = 6	Block, brown
F(000) = 1836	0.15 × 0.10 × 0.07 mm

Data collection

PHOTON 100 CMOS detector diffractometer	2412 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.106
φ and ω scans	θmax = 26.1°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −17→17
Tmin = 0.700, Tmax = 0.744	k = −17→17
125055 measured reflections	l = −29→29
2614 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.024	H-atom parameters constrained
wR(F^2) = 0.054	w = 1/[σ^2(Fo^2) + (0.0277P)^2 + 0.9047P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
2614 reflections	Δρmax = 0.22 e Å^−3
179 parameters	Δρmin = −0.14 e Å^−3
0 restraints	Absolute structure: Flack x determined using 894 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013).
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.002 (5)

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
Ni1	0.41510 (3)	0.0000	0.0000	0.01866 (12)
Cl1	0.44000 (6)	0.03687 (5)	−0.09968 (3)	0.03369 (17)
N1	0.56034 (18)	0.0000	0.0000	0.0181 (6)
N2	0.75658 (19)	0.0000	0.0000	0.0204 (6)
N3	0.53182 (16)	0.17007 (16)	0.01208 (8)	0.0196 (4)
N4	0.86393 (17)	0.24353 (17)	0.07265 (9)	0.0265 (5)
N5	0.2636 (2)	0.0000	0.0000	0.0303 (7)
C1	0.65538 (19)	0.09724 (18)	0.00453 (10)	0.0177 (5)
C2	0.75545 (19)	0.09505 (19)	0.00914 (9)	0.0194 (5)
C3	0.6391 (2)	0.19584 (19)	0.00471 (10)	0.0187 (5)
C4	0.7236 (2)	0.30472 (19)	−0.00359 (11)	0.0242 (5)
H4	0.7967	0.3205	−0.0114	0.029*
C5	0.6992 (2)	0.3896 (2)	−0.00019 (12)	0.0290 (6)
H5	0.7557	0.4642	−0.0056	0.035*
C6	0.5912 (2)	0.3645 (2)	0.01124 (10)	0.0279 (6)
H6	0.5734	0.4213	0.0157	0.033*
C7	0.5104 (2)	0.2537 (2)	0.01591 (10)	0.0236 (6)
H7	0.4362	0.2361	0.0221	0.028*
C8	0.8647 (2)	0.1935 (2)	0.02484 (10)	0.0199 (5)
C9	0.9581 (2)	0.2297 (2)	−0.00795 (12)	0.0299 (6)
H9	0.9555	0.1912	−0.0408	0.036*
C10	1.0561 (2)	0.3239 (2)	0.00830 (12)	0.0385 (7)
H10	1.1210	0.3514	−0.0137	0.046*
C11	1.0565 (2)	0.3761 (2)	0.05722 (11)	0.0323 (6)
H11	1.1217	0.4403	0.0694	0.039*
C12	0.9594 (2)	0.3327 (2)	0.08824 (11)	0.0309 (6)
H12	0.9608	0.3679	0.1221	0.037*
C13	0.1829 (2)	−0.0605 (2)	0.03686 (14)	0.0414 (7)
H13	0.1959	−0.1024	0.0638	0.050*
C14	0.0811 (3)	−0.0642 (3)	0.03700 (18)	0.0579 (10)
H14	0.0250	−0.1105	0.0624	0.070*
C15	0.0629 (3)	0.0000	0.0000	0.0639 (15)
H15	−0.0051	0.0000	0.0000	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.01813 (17)	0.0145 (2)	0.0222 (2)	0.00723 (11)	0.00093 (9)	0.00185 (17)
Cl1	0.0480 (4)	0.0269 (3)	0.0215 (3)	0.0152 (3)	−0.0012 (3)	0.0025 (2)
N1	0.0175 (10)	0.0147 (13)	0.0210 (14)	0.0073 (7)	−0.0002 (6)	−0.0003 (12)
N2	0.0200 (11)	0.0174 (14)	0.0231 (15)	0.0087 (7)	−0.0006 (6)	−0.0012 (13)
N3	0.0212 (10)	0.0172 (10)	0.0196 (10)	0.0091 (9)	0.0005 (8)	0.0004 (8)
N4	0.0234 (11)	0.0264 (11)	0.0231 (11)	0.0074 (9)	0.0023 (9)	−0.0022 (9)
N5	0.0247 (12)	0.0244 (16)	0.0417 (19)	0.0122 (8)	0.0024 (8)	0.0048 (15)
C1	0.0189 (11)	0.0155 (11)	0.0171 (12)	0.0073 (9)	0.0013 (10)	−0.0007 (9)
C2	0.0195 (12)	0.0165 (12)	0.0194 (12)	0.0069 (10)	0.0017 (10)	0.0010 (10)
C3	0.0220 (12)	0.0163 (11)	0.0176 (11)	0.0095 (10)	−0.0010 (10)	−0.0016 (10)
C4	0.0192 (13)	0.0189 (12)	0.0329 (14)	0.0082 (10)	0.0026 (11)	0.0010 (11)
C5	0.0285 (14)	0.0168 (12)	0.0393 (16)	0.0094 (11)	0.0007 (13)	0.0016 (12)
C6	0.0345 (14)	0.0184 (12)	0.0351 (14)	0.0166 (12)	0.0002 (12)	−0.0012 (11)
C7	0.0257 (13)	0.0237 (13)	0.0254 (14)	0.0153 (11)	0.0025 (10)	0.0015 (10)
C8	0.0186 (12)	0.0160 (12)	0.0241 (13)	0.0080 (10)	−0.0010 (10)	−0.0004 (10)
C9	0.0228 (13)	0.0280 (14)	0.0321 (15)	0.0075 (11)	0.0047 (12)	−0.0085 (12)
C10	0.0206 (14)	0.0381 (16)	0.0406 (18)	0.0025 (12)	0.0078 (12)	−0.0054 (14)
C11	0.0227 (14)	0.0252 (15)	0.0332 (16)	0.0003 (12)	−0.0021 (12)	−0.0018 (12)
C12	0.0319 (14)	0.0260 (14)	0.0232 (13)	0.0057 (12)	−0.0020 (12)	−0.0053 (11)
C13	0.0311 (16)	0.0357 (17)	0.0571 (19)	0.0166 (15)	0.0107 (15)	0.0109 (15)
C14	0.0347 (18)	0.057 (2)	0.082 (3)	0.0222 (17)	0.0195 (18)	0.013 (2)
C15	0.0362 (19)	0.067 (4)	0.098 (5)	0.0336 (18)	0.0005 (18)	0.001 (4)

Geometric parameters (Å, º)

Ni1—N1	2.008 (3)	C4—H4	0.9400
Ni1—N5	2.094 (3)	C5—C6	1.380 (4)
Ni1—N3^i	2.1026 (19)	C5—H5	0.9400
Ni1—N3	2.1026 (19)	C6—C7	1.377 (4)
Ni1—Cl1^i	2.4238 (6)	C6—H6	0.9400
Ni1—Cl1	2.4238 (6)	C7—H7	0.9400
N1—C1	1.334 (3)	C8—C9	1.373 (3)
N1—C1^i	1.334 (3)	C9—C10	1.385 (4)
N2—C2^i	1.340 (3)	C9—H9	0.9400
N2—C2	1.340 (3)	C10—C11	1.373 (4)
N3—C7	1.332 (3)	C10—H10	0.9400
N3—C3	1.353 (3)	C11—C12	1.380 (4)
N4—C12	1.332 (3)	C11—H11	0.9400
N4—C8	1.338 (3)	C12—H12	0.9400
N5—C13^i	1.337 (3)	C13—C14	1.382 (4)
N5—C13	1.337 (3)	C13—H13	0.9400
C1—C2	1.403 (3)	C14—C15	1.362 (4)
C1—C3	1.488 (3)	C14—H14	0.9400
C2—C8	1.489 (3)	C15—C14^i	1.362 (4)
C3—C4	1.382 (3)	C15—H15	0.9400
C4—C5	1.377 (4)
N1—Ni1—N5	180.0	C5—C4—H4	120.5
N1—Ni1—N3^i	77.97 (5)	C3—C4—H4	120.5
N5—Ni1—N3^i	102.03 (5)	C4—C5—C6	119.5 (2)
N1—Ni1—N3	77.97 (5)	C4—C5—H5	120.3
N5—Ni1—N3	102.03 (5)	C6—C5—H5	120.3
N3^i—Ni1—N3	155.95 (11)	C7—C6—C5	118.0 (2)
N1—Ni1—Cl1^i	87.89 (2)	C7—C6—H6	121.0
N5—Ni1—Cl1^i	92.11 (2)	C5—C6—H6	121.0
N3^i—Ni1—Cl1^i	87.19 (5)	N3—C7—C6	123.4 (2)
N3—Ni1—Cl1^i	91.94 (5)	N3—C7—H7	118.3
N1—Ni1—Cl1	87.89 (2)	C6—C7—H7	118.3
N5—Ni1—Cl1	92.11 (2)	N4—C8—C9	123.2 (2)
N3^i—Ni1—Cl1	91.93 (5)	N4—C8—C2	114.9 (2)
N3—Ni1—Cl1	87.18 (5)	C9—C8—C2	121.9 (2)
Cl1^i—Ni1—Cl1	175.77 (4)	C8—C9—C10	118.8 (2)
C1—N1—C1^i	122.5 (3)	C8—C9—H9	120.6
C1—N1—Ni1	118.76 (13)	C10—C9—H9	120.6
C1^i—N1—Ni1	118.76 (13)	C11—C10—C9	118.6 (2)
C2^i—N2—C2	119.7 (3)	C11—C10—H10	120.7
C7—N3—C3	118.1 (2)	C9—C10—H10	120.7
C7—N3—Ni1	126.90 (16)	C10—C11—C12	118.7 (2)
C3—N3—Ni1	113.83 (15)	C10—C11—H11	120.6
C12—N4—C8	117.2 (2)	C12—C11—H11	120.6
C13^i—N5—C13	117.1 (4)	N4—C12—C11	123.4 (3)
C13^i—N5—Ni1	121.44 (18)	N4—C12—H12	118.3
C13—N5—Ni1	121.44 (18)	C11—C12—H12	118.3
N1—C1—C2	118.0 (2)	N5—C13—C14	122.7 (3)
N1—C1—C3	113.6 (2)	N5—C13—H13	118.7
C2—C1—C3	128.4 (2)	C14—C13—H13	118.7
N2—C2—C1	120.2 (2)	C15—C14—C13	119.4 (4)
N2—C2—C8	115.7 (2)	C15—C14—H14	120.3
C1—C2—C8	124.0 (2)	C13—C14—H14	120.3
N3—C3—C4	121.6 (2)	C14^i—C15—C14	118.6 (5)
N3—C3—C1	114.0 (2)	C14^i—C15—H15	120.7
C4—C3—C1	124.4 (2)	C14—C15—H15	120.7
C5—C4—C3	119.1 (2)
C1^i—N1—C1—C2	−5.20 (15)	C4—C5—C6—C7	−3.4 (4)
Ni1—N1—C1—C2	174.80 (15)	C3—N3—C7—C6	1.8 (4)
C1^i—N1—C1—C3	175.6 (2)	Ni1—N3—C7—C6	−164.88 (19)
Ni1—N1—C1—C3	−4.4 (2)	C5—C6—C7—N3	2.6 (4)
C2^i—N2—C2—C1	−5.36 (16)	C12—N4—C8—C9	0.2 (4)
C2^i—N2—C2—C8	173.8 (2)	C12—N4—C8—C2	−179.4 (2)
N1—C1—C2—N2	10.7 (3)	N2—C2—C8—N4	−125.1 (2)
C3—C1—C2—N2	−170.2 (2)	C1—C2—C8—N4	54.0 (3)
N1—C1—C2—C8	−168.31 (19)	N2—C2—C8—C9	55.3 (3)
C3—C1—C2—C8	10.8 (4)	C1—C2—C8—C9	−125.6 (3)
C7—N3—C3—C4	−5.6 (4)	N4—C8—C9—C10	−1.4 (4)
Ni1—N3—C3—C4	162.80 (19)	C2—C8—C9—C10	178.1 (3)
C7—N3—C3—C1	176.4 (2)	C8—C9—C10—C11	1.3 (5)
Ni1—N3—C3—C1	−15.3 (3)	C9—C10—C11—C12	0.1 (5)
N1—C1—C3—N3	13.1 (3)	C8—N4—C12—C11	1.3 (4)
C2—C1—C3—N3	−166.0 (2)	C10—C11—C12—N4	−1.4 (5)
N1—C1—C3—C4	−164.9 (2)	C13^i—N5—C13—C14	1.5 (3)
C2—C1—C3—C4	16.0 (4)	Ni1—N5—C13—C14	−178.5 (3)
N3—C3—C4—C5	4.8 (4)	N5—C13—C14—C15	−3.1 (5)
C1—C3—C4—C5	−177.3 (2)	C13—C14—C15—C14^i	1.5 (3)
C3—C4—C5—C6	−0.2 (4)

Symmetry code: (i) x−y, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cl1^ii	0.94	2.78	3.513 (3)	136
C10—H10···N4^iii	0.94	2.46	3.360 (3)	161
C12—H12···Cl1^iv	0.94	2.71	3.602 (3)	160
C13—H13···Cl1^i	0.94	2.68	3.261 (3)	121

Symmetry codes: (i) x−y, −y, −z; (ii) x−y, x, z+1/6; (iii) y+1, −x+y+1, z−1/6; (iv) −y+1, x−y, z+1/3.