The title compound, [Ni2Cl2(μ-Cl)2(C10H8N2)2(C3H7NO)2], exists as a centrosymmetric dimer of two octahedral nickel centers. In the crystal, two chloride ions bridge the two nickel centers with one terminal chloride ion bound to each nickel atom. Coupled with a chelating bipyridine ligand and an O-bound N,N-dimethylformamide solvent molecule, each nickel center exhibits an slightly distorted octahedral coordination environment. The meridional chloride ions all sit in equatorial positions, with the bipyridine ligand occupying one equatorial and one axial position, and the N,N-dimethylformamide ligand occupying the final axial position. The 2,2′-bipyridine ligand binds to nickel in a near planar fashion, with the non-H atoms possessing a mean devation from planarity of 0.046 Å. No π–π interactions are observed in the crystal.
Supporting information
CCDC reference: 1453181
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.032
- wR factor = 0.073
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT120_ALERT_1_C Reported SPGR Pbca Inconsistent with Explicit Pbca Chec
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 12 Report
Alert level G
PLAT795_ALERT_4_G C-Atom in CIF Coordinate List out of Sequence .. C1 Note
PLAT797_ALERT_4_G N-Atom in CIF Coordinate List out of Sequence .. N1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 8 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF .... 1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density 5 Note
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
5 ALERT level G = General information/check it is not something unexpected
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009)
and publCIF (Westrip, 2010).
Di-µ-chlorido-bis[(2,2'-bipyridine-
κ2N,
N')chlorido(
N,
N-dimethylformamide-
κO)nickel(II)]
top
Crystal data top
[Ni2Cl4(C10H8N2)2(C3H7NO)2] | F(000) = 1472 |
Mr = 717.78 | Dx = 1.686 Mg m−3 |
Orthorhombic, Pbca | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: -P 2ab 2ac | Cell parameters from 5383 reflections |
a = 11.9130 (9) Å | θ = 4.3–70.2° |
b = 11.445 (1) Å | µ = 5.44 mm−1 |
c = 20.7458 (17) Å | T = 120 K |
V = 2828.6 (4) Å3 | Plate, green |
Z = 4 | 0.15 × 0.05 × 0.02 mm |
Data collection top
Bruker D8 Venture CMOS diffractometer | 2670 independent reflections |
Radiation source: Cu | 2139 reflections with I > 2σ(I) |
HELIOS MX monochromator | Rint = 0.053 |
φ and ω scans | θmax = 70.2°, θmin = 4.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | h = −14→13 |
Tmin = 0.240, Tmax = 0.384 | k = −13→11 |
12752 measured reflections | l = −19→25 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.032 | H-atom parameters constrained |
wR(F2) = 0.073 | w = 1/[σ2(Fo2) + (0.0299P)2 + 1.4865P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
2670 reflections | Δρmax = 0.26 e Å−3 |
183 parameters | Δρmin = −0.30 e Å−3 |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Ni1 | 0.49476 (3) | 0.38808 (4) | 0.43948 (2) | 0.01585 (12) | |
Cl2 | 0.63495 (4) | 0.46540 (5) | 0.51055 (3) | 0.01834 (14) | |
Cl1 | 0.61409 (5) | 0.25008 (6) | 0.38155 (3) | 0.02148 (15) | |
O1 | 0.45006 (13) | 0.26410 (15) | 0.50647 (8) | 0.0190 (4) | |
N2 | 0.36328 (15) | 0.34487 (17) | 0.37970 (9) | 0.0156 (4) | |
N1 | 0.52288 (15) | 0.50115 (17) | 0.36496 (9) | 0.0168 (4) | |
N3 | 0.49296 (15) | 0.10292 (18) | 0.56455 (10) | 0.0196 (4) | |
C5 | 0.45302 (18) | 0.4894 (2) | 0.31397 (11) | 0.0167 (5) | |
C6 | 0.35961 (18) | 0.4053 (2) | 0.32359 (11) | 0.0171 (5) | |
C10 | 0.28304 (18) | 0.2671 (2) | 0.39238 (12) | 0.0198 (5) | |
H10 | 0.2855 | 0.2259 | 0.4321 | 0.024* | |
C11 | 0.51802 (19) | 0.1879 (2) | 0.52417 (11) | 0.0191 (5) | |
H11 | 0.5923 | 0.1911 | 0.5076 | 0.023* | |
C1 | 0.60826 (19) | 0.5763 (2) | 0.36081 (11) | 0.0196 (5) | |
H1 | 0.6561 | 0.5859 | 0.3971 | 0.023* | |
C4 | 0.4687 (2) | 0.5525 (2) | 0.25765 (11) | 0.0202 (5) | |
H4 | 0.4184 | 0.5435 | 0.2225 | 0.024* | |
C2 | 0.6298 (2) | 0.6409 (2) | 0.30573 (12) | 0.0231 (6) | |
H2 | 0.6922 | 0.6924 | 0.3039 | 0.028* | |
C8 | 0.19164 (19) | 0.3053 (2) | 0.29244 (12) | 0.0233 (6) | |
H8 | 0.1328 | 0.2913 | 0.2625 | 0.028* | |
C9 | 0.19615 (19) | 0.2441 (2) | 0.34992 (12) | 0.0225 (6) | |
H9 | 0.1407 | 0.1873 | 0.3600 | 0.027* | |
C12 | 0.5762 (2) | 0.0156 (2) | 0.58366 (12) | 0.0242 (6) | |
H12A | 0.6429 | 0.0231 | 0.5564 | 0.036* | |
H12B | 0.5442 | −0.0628 | 0.5786 | 0.036* | |
H12C | 0.5971 | 0.0279 | 0.6288 | 0.036* | |
C7 | 0.27354 (18) | 0.3871 (2) | 0.27914 (11) | 0.0197 (5) | |
H7 | 0.2713 | 0.4305 | 0.2401 | 0.024* | |
C3 | 0.5587 (2) | 0.6290 (2) | 0.25328 (12) | 0.0237 (6) | |
H3 | 0.5714 | 0.6726 | 0.2150 | 0.028* | |
C13 | 0.3814 (2) | 0.0931 (3) | 0.59311 (13) | 0.0298 (6) | |
H13A | 0.3298 | 0.1462 | 0.5709 | 0.045* | |
H13B | 0.3852 | 0.1139 | 0.6389 | 0.045* | |
H13C | 0.3545 | 0.0126 | 0.5887 | 0.045* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.0160 (2) | 0.0169 (2) | 0.0146 (2) | −0.00102 (17) | −0.00107 (15) | 0.00083 (17) |
Cl2 | 0.0161 (3) | 0.0210 (3) | 0.0179 (3) | 0.0006 (2) | −0.0021 (2) | −0.0016 (2) |
Cl1 | 0.0209 (3) | 0.0220 (3) | 0.0215 (3) | 0.0016 (2) | 0.0026 (2) | −0.0017 (2) |
O1 | 0.0196 (8) | 0.0193 (10) | 0.0180 (8) | −0.0006 (7) | 0.0003 (6) | 0.0032 (7) |
N2 | 0.0158 (9) | 0.0149 (11) | 0.0160 (10) | 0.0000 (8) | 0.0001 (8) | −0.0025 (8) |
N1 | 0.0173 (9) | 0.0171 (12) | 0.0160 (9) | 0.0018 (8) | 0.0012 (8) | 0.0001 (8) |
N3 | 0.0186 (9) | 0.0192 (12) | 0.0209 (10) | 0.0006 (9) | −0.0008 (8) | 0.0023 (9) |
C5 | 0.0166 (11) | 0.0180 (14) | 0.0156 (11) | 0.0036 (10) | 0.0008 (9) | −0.0015 (10) |
C6 | 0.0173 (11) | 0.0171 (14) | 0.0169 (11) | 0.0036 (10) | 0.0024 (9) | −0.0026 (10) |
C10 | 0.0204 (11) | 0.0181 (14) | 0.0208 (12) | 0.0003 (10) | 0.0037 (9) | −0.0005 (10) |
C11 | 0.0178 (11) | 0.0222 (14) | 0.0174 (11) | −0.0032 (11) | −0.0019 (9) | −0.0023 (11) |
C1 | 0.0195 (11) | 0.0200 (14) | 0.0192 (12) | −0.0008 (10) | −0.0003 (10) | −0.0023 (10) |
C4 | 0.0245 (12) | 0.0212 (15) | 0.0148 (11) | 0.0023 (11) | −0.0003 (9) | −0.0003 (10) |
C2 | 0.0215 (12) | 0.0215 (15) | 0.0263 (13) | −0.0029 (11) | 0.0025 (10) | 0.0025 (11) |
C8 | 0.0177 (11) | 0.0291 (17) | 0.0230 (13) | 0.0020 (11) | −0.0019 (10) | −0.0091 (12) |
C9 | 0.0182 (11) | 0.0200 (15) | 0.0294 (13) | −0.0023 (10) | 0.0029 (10) | −0.0067 (12) |
C12 | 0.0264 (13) | 0.0218 (15) | 0.0242 (13) | 0.0013 (11) | −0.0058 (10) | 0.0020 (11) |
C7 | 0.0206 (11) | 0.0225 (15) | 0.0161 (11) | 0.0043 (11) | −0.0003 (9) | 0.0005 (10) |
C3 | 0.0284 (13) | 0.0240 (16) | 0.0187 (12) | 0.0011 (11) | 0.0054 (10) | 0.0048 (11) |
C13 | 0.0247 (13) | 0.0319 (17) | 0.0329 (15) | −0.0003 (12) | 0.0052 (11) | 0.0109 (13) |
Geometric parameters (Å, º) top
Ni1—Cl2 | 2.3971 (7) | C11—H11 | 0.9500 |
Ni1—Cl2i | 2.5049 (7) | C1—H1 | 0.9500 |
Ni1—Cl1 | 2.4413 (7) | C1—C2 | 1.385 (3) |
Ni1—O1 | 2.0563 (17) | C4—H4 | 0.9500 |
Ni1—N2 | 2.0582 (19) | C4—C3 | 1.387 (4) |
Ni1—N1 | 2.044 (2) | C2—H2 | 0.9500 |
Cl2—Ni1i | 2.5049 (7) | C2—C3 | 1.385 (3) |
O1—C11 | 1.246 (3) | C8—H8 | 0.9500 |
N2—C6 | 1.355 (3) | C8—C9 | 1.384 (4) |
N2—C10 | 1.332 (3) | C8—C7 | 1.380 (3) |
N1—C5 | 1.353 (3) | C9—H9 | 0.9500 |
N1—C1 | 1.335 (3) | C12—H12A | 0.9800 |
N3—C11 | 1.318 (3) | C12—H12B | 0.9800 |
N3—C12 | 1.463 (3) | C12—H12C | 0.9800 |
N3—C13 | 1.459 (3) | C7—H7 | 0.9500 |
C5—C6 | 1.484 (3) | C3—H3 | 0.9500 |
C5—C4 | 1.387 (3) | C13—H13A | 0.9800 |
C6—C7 | 1.395 (3) | C13—H13B | 0.9800 |
C10—H10 | 0.9500 | C13—H13C | 0.9800 |
C10—C9 | 1.385 (3) | | |
| | | |
Cl2—Ni1—Cl2i | 85.88 (2) | O1—C11—H11 | 118.1 |
Cl2—Ni1—Cl1 | 97.81 (2) | N3—C11—H11 | 118.1 |
Cl1—Ni1—Cl2i | 174.92 (2) | N1—C1—H1 | 118.7 |
O1—Ni1—Cl2i | 91.29 (5) | N1—C1—C2 | 122.6 (2) |
O1—Ni1—Cl2 | 91.12 (5) | C2—C1—H1 | 118.7 |
O1—Ni1—Cl1 | 92.13 (5) | C5—C4—H4 | 120.4 |
O1—Ni1—N2 | 92.55 (7) | C5—C4—C3 | 119.2 (2) |
N2—Ni1—Cl2i | 86.61 (6) | C3—C4—H4 | 120.4 |
N2—Ni1—Cl2 | 171.71 (6) | C1—C2—H2 | 120.6 |
N2—Ni1—Cl1 | 89.49 (6) | C1—C2—C3 | 118.8 (2) |
N1—Ni1—Cl2 | 96.73 (6) | C3—C2—H2 | 120.6 |
N1—Ni1—Cl2i | 89.44 (6) | C9—C8—H8 | 120.4 |
N1—Ni1—Cl1 | 86.66 (6) | C7—C8—H8 | 120.4 |
N1—Ni1—O1 | 172.15 (7) | C7—C8—C9 | 119.2 (2) |
N1—Ni1—N2 | 79.69 (8) | C10—C9—H9 | 120.6 |
Ni1—Cl2—Ni1i | 94.12 (2) | C8—C9—C10 | 118.7 (2) |
C11—O1—Ni1 | 120.95 (15) | C8—C9—H9 | 120.6 |
C6—N2—Ni1 | 114.81 (15) | N3—C12—H12A | 109.5 |
C10—N2—Ni1 | 125.98 (16) | N3—C12—H12B | 109.5 |
C10—N2—C6 | 119.2 (2) | N3—C12—H12C | 109.5 |
C5—N1—Ni1 | 115.31 (16) | H12A—C12—H12B | 109.5 |
C1—N1—Ni1 | 125.58 (16) | H12A—C12—H12C | 109.5 |
C1—N1—C5 | 118.8 (2) | H12B—C12—H12C | 109.5 |
C11—N3—C12 | 121.5 (2) | C6—C7—H7 | 120.4 |
C11—N3—C13 | 121.4 (2) | C8—C7—C6 | 119.3 (2) |
C13—N3—C12 | 117.0 (2) | C8—C7—H7 | 120.4 |
N1—C5—C6 | 114.9 (2) | C4—C3—H3 | 120.6 |
N1—C5—C4 | 121.6 (2) | C2—C3—C4 | 118.9 (2) |
C4—C5—C6 | 123.5 (2) | C2—C3—H3 | 120.6 |
N2—C6—C5 | 115.0 (2) | N3—C13—H13A | 109.5 |
N2—C6—C7 | 121.0 (2) | N3—C13—H13B | 109.5 |
C7—C6—C5 | 124.0 (2) | N3—C13—H13C | 109.5 |
N2—C10—H10 | 118.7 | H13A—C13—H13B | 109.5 |
N2—C10—C9 | 122.5 (2) | H13A—C13—H13C | 109.5 |
C9—C10—H10 | 118.7 | H13B—C13—H13C | 109.5 |
O1—C11—N3 | 123.8 (2) | | |
| | | |
Ni1—O1—C11—N3 | −176.70 (18) | C5—C4—C3—C2 | −0.6 (4) |
Ni1—N2—C6—C5 | 1.9 (3) | C6—N2—C10—C9 | 0.9 (4) |
Ni1—N2—C6—C7 | −178.44 (18) | C6—C5—C4—C3 | −180.0 (2) |
Ni1—N2—C10—C9 | 179.02 (18) | C10—N2—C6—C5 | −179.8 (2) |
Ni1—N1—C5—C6 | 6.5 (3) | C10—N2—C6—C7 | −0.1 (3) |
Ni1—N1—C5—C4 | −173.88 (18) | C1—N1—C5—C6 | −179.0 (2) |
Ni1—N1—C1—C2 | 172.30 (19) | C1—N1—C5—C4 | 0.6 (3) |
N2—C6—C7—C8 | −0.6 (4) | C1—C2—C3—C4 | −0.3 (4) |
N2—C10—C9—C8 | −0.9 (4) | C4—C5—C6—N2 | 174.8 (2) |
N1—C5—C6—N2 | −5.6 (3) | C4—C5—C6—C7 | −4.8 (4) |
N1—C5—C6—C7 | 174.8 (2) | C9—C8—C7—C6 | 0.6 (4) |
N1—C5—C4—C3 | 0.5 (4) | C12—N3—C11—O1 | 180.0 (2) |
N1—C1—C2—C3 | 1.4 (4) | C7—C8—C9—C10 | 0.1 (4) |
C5—N1—C1—C2 | −1.5 (4) | C13—N3—C11—O1 | −1.2 (4) |
C5—C6—C7—C8 | 179.0 (2) | | |
Symmetry code: (i) −x+1, −y+1, −z+1. |