Poly[bis­[μ₂-4,4′-bis­(imidazol-1-ylmeth­yl)biphenyl-κ²N:N′]di­chlorido­nickel(II)]

In the title compound, [NiCl₂(C₂₀H₁₈N₄)₂]_n, the Ni²⁺ cation is situated on an inversion center and is coordinated by two chloride ions and four imidazole N atoms of four different 4,4′-bis­[(1H-imidazol-1-yl)meth­yl]-1,1′-biphenyl (BIMB), forming a slightly distorted octa­hedral geometry. Each BIMB ligand adopts a linear linker to connect Ni²⁺ ions, forming a two-dimensional layer with an sql network. In the crystal, neighboring layers repeat in an ABAB stacking mode, and weak inter­molecular C—H...Cl hydrogen bonds between alternate layers lead to a three-dimensional, twofold inter­penetrated, supra­molecular framework with a pcu topology net.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.072
• wR factor = 0.161
• Data-to-parameter ratio = 18.7

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.26 Report
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00633 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     22.542 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      4.431 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.213 Check
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension          2 Info
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large       5.35 Why ?
PLAT794_ALERT_5_G Tentative Bond Valency for Ni1       (II)      .       1.92 Info
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        523 Note

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

---

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: DIAMOND (Brandenburg, 1999).

Poly[bis[µ₂-4,4'-bis(imidazol-1-ylmethyl)biphenyl-κ²N:N']dichloridonickel(II)]

Crystal data

[NiCl2(C20H18N4)2]	F(000) = 1576
Mr = 758.38	Dx = 1.432 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 26.453 (3) Å	Cell parameters from 3041 reflections
b = 7.3571 (7) Å	θ = 2.7–22.6°
c = 18.099 (2) Å	µ = 0.75 mm^−1
β = 93.223 (11)°	T = 296 K
V = 3516.8 (7) Å^3	Needle, green
Z = 4	0.30 × 0.22 × 0.16 mm

Data collection

Oxford Diffraction, Xcalibur, Eos, Gemini diffractometer	2543 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tube	Rint = 0.078
ω scans	θmax = 29.5°, θmin = 2.3°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2015)	h = −35→35
Tmin = 0.856, Tmax = 1.000	k = −9→10
16025 measured reflections	l = −24→19
4343 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.161	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0438P)^2 + 5.351P] where P = (Fo^2 + 2Fc^2)/3
4343 reflections	(Δ/σ)max < 0.001
232 parameters	Δρmax = 0.61 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

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.

Refinement. All H atoms were placed in idealized positions (C—H = 0.93 Å for aromatic H; C—H = 0.97 Å for methylene H) and refined as riding atoms with U_iso(H) = 1.2U_eq(C).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ni1	0.250000	0.250000	0.500000	0.0419 (2)
Cl1	0.21866 (4)	0.51154 (14)	0.57071 (6)	0.0488 (3)
N1	0.22244 (12)	0.3739 (5)	0.40075 (19)	0.0423 (8)
N2	0.20188 (12)	0.5693 (5)	0.31205 (19)	0.0454 (9)
N3	0.32078 (12)	0.3777 (5)	0.49579 (19)	0.0451 (9)
N4	0.38019 (12)	0.5864 (5)	0.4895 (2)	0.0454 (9)
C1	0.21920 (15)	0.5462 (6)	0.3818 (2)	0.0480 (11)
H1	0.228055	0.641502	0.413725	0.058*
C2	0.19229 (17)	0.4035 (7)	0.2839 (3)	0.0605 (13)
H2	0.179357	0.375818	0.236414	0.073*
C3	0.20524 (17)	0.2848 (7)	0.3387 (3)	0.0594 (13)
H3	0.202711	0.159098	0.334459	0.071*
C4	0.19061 (16)	0.7409 (7)	0.2746 (3)	0.0598 (13)
H4A	0.205060	0.740434	0.226555	0.072*
H4B	0.205927	0.839897	0.303368	0.072*
C5	0.13415 (16)	0.7708 (6)	0.2650 (3)	0.0485 (11)
C6	0.10774 (17)	0.7322 (6)	0.1991 (3)	0.0555 (12)
H6	0.125207	0.697958	0.158149	0.067*
C7	0.05550 (17)	0.7438 (6)	0.1933 (3)	0.0511 (11)
H7	0.038471	0.716996	0.148230	0.061*
C8	0.02803 (15)	0.7940 (5)	0.2523 (2)	0.0443 (11)
C9	0.05500 (17)	0.8394 (7)	0.3182 (3)	0.0568 (12)
H9	0.037767	0.877617	0.358795	0.068*
C10	0.10719 (17)	0.8279 (7)	0.3234 (3)	0.0601 (13)
H10	0.124556	0.859617	0.367591	0.072*
C11	0.33046 (15)	0.5513 (6)	0.4876 (2)	0.0460 (11)
H11	0.305554	0.639986	0.481224	0.055*
C12	0.36761 (17)	0.2989 (6)	0.5055 (3)	0.0573 (13)
H12	0.373160	0.175661	0.513987	0.069*
C13	0.40491 (18)	0.4252 (6)	0.5009 (3)	0.0580 (13)
H13	0.439701	0.405819	0.504830	0.070*
C14	0.40289 (17)	0.7651 (6)	0.4815 (3)	0.0523 (12)
H14A	0.425099	0.790809	0.524742	0.063*
H14B	0.376426	0.856560	0.478823	0.063*
C15	0.43247 (16)	0.7761 (6)	0.4137 (3)	0.0474 (11)
C16	0.48277 (16)	0.8245 (6)	0.4154 (3)	0.0558 (12)
H16	0.499348	0.852339	0.460692	0.067*
C17	0.50950 (17)	0.8329 (7)	0.3518 (3)	0.0588 (13)
H17	0.543335	0.867828	0.354691	0.071*
C18	0.48594 (16)	0.7894 (5)	0.2841 (2)	0.0468 (11)
C19	0.43553 (17)	0.7414 (6)	0.2819 (3)	0.0544 (12)
H19	0.418879	0.713521	0.236701	0.065*
C20	0.40927 (17)	0.7340 (6)	0.3457 (3)	0.0556 (12)
H20	0.375352	0.700011	0.342800	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0420 (4)	0.0360 (4)	0.0478 (5)	0.0039 (3)	0.0020 (3)	0.0062 (4)
Cl1	0.0494 (6)	0.0406 (6)	0.0563 (7)	0.0077 (5)	0.0024 (5)	0.0018 (5)
N1	0.0364 (19)	0.042 (2)	0.048 (2)	−0.0009 (16)	−0.0007 (16)	0.0031 (17)
N2	0.0367 (19)	0.050 (2)	0.049 (2)	0.0005 (17)	−0.0055 (16)	0.0120 (18)
N3	0.0380 (19)	0.039 (2)	0.059 (2)	0.0035 (16)	0.0041 (17)	0.0061 (18)
N4	0.040 (2)	0.036 (2)	0.060 (2)	−0.0003 (16)	0.0051 (17)	0.0076 (17)
C1	0.046 (3)	0.047 (3)	0.050 (3)	−0.002 (2)	−0.007 (2)	0.000 (2)
C2	0.060 (3)	0.060 (3)	0.059 (3)	0.014 (3)	−0.016 (2)	−0.005 (3)
C3	0.055 (3)	0.046 (3)	0.075 (4)	0.009 (2)	−0.013 (3)	−0.005 (3)
C4	0.044 (3)	0.065 (3)	0.069 (3)	−0.003 (2)	−0.004 (2)	0.027 (3)
C5	0.045 (2)	0.045 (3)	0.055 (3)	0.000 (2)	−0.005 (2)	0.015 (2)
C6	0.052 (3)	0.056 (3)	0.058 (3)	0.005 (2)	−0.004 (2)	0.002 (2)
C7	0.053 (3)	0.051 (3)	0.048 (3)	−0.001 (2)	−0.013 (2)	−0.002 (2)
C8	0.048 (2)	0.037 (2)	0.046 (3)	−0.0001 (18)	−0.009 (2)	0.004 (2)
C9	0.053 (3)	0.068 (3)	0.048 (3)	0.002 (2)	−0.006 (2)	−0.001 (3)
C10	0.052 (3)	0.072 (3)	0.055 (3)	−0.002 (3)	−0.018 (2)	0.001 (3)
C11	0.037 (2)	0.045 (3)	0.056 (3)	0.0067 (19)	0.001 (2)	0.006 (2)
C12	0.055 (3)	0.040 (3)	0.077 (4)	0.008 (2)	0.007 (3)	0.012 (2)
C13	0.049 (3)	0.046 (3)	0.079 (4)	0.008 (2)	0.002 (2)	0.004 (3)
C14	0.051 (3)	0.046 (3)	0.060 (3)	−0.003 (2)	0.005 (2)	−0.001 (2)
C15	0.045 (2)	0.040 (3)	0.057 (3)	0.001 (2)	0.003 (2)	0.001 (2)
C16	0.044 (3)	0.062 (3)	0.061 (3)	−0.004 (2)	0.000 (2)	0.000 (3)
C17	0.039 (2)	0.060 (3)	0.078 (4)	−0.006 (2)	0.005 (2)	−0.002 (3)
C18	0.046 (3)	0.032 (2)	0.062 (3)	0.0030 (18)	0.005 (2)	0.000 (2)
C19	0.048 (3)	0.058 (3)	0.057 (3)	−0.002 (2)	−0.001 (2)	−0.002 (2)
C20	0.043 (3)	0.058 (3)	0.066 (3)	−0.004 (2)	0.003 (2)	−0.001 (3)

Geometric parameters (Å, º)

Ni1—N3^i	2.100 (3)	C6—H6	0.9300
Ni1—N3	2.100 (3)	C7—C8	1.377 (6)
Ni1—N1	2.108 (3)	C7—H7	0.9300
Ni1—N1^i	2.108 (3)	C8—C9	1.395 (6)
Ni1—Cl1	2.4793 (11)	C8—C8^ii	1.480 (8)
Ni1—Cl1^i	2.4793 (11)	C9—C10	1.381 (6)
N1—C1	1.315 (5)	C9—H9	0.9300
N1—C3	1.357 (5)	C10—H10	0.9300
N2—C1	1.330 (5)	C11—H11	0.9300
N2—C2	1.341 (6)	C12—C13	1.361 (6)
N2—C4	1.456 (5)	C12—H12	0.9300
N3—C11	1.312 (5)	C13—H13	0.9300
N3—C12	1.370 (5)	C14—C15	1.495 (6)
N4—C11	1.339 (5)	C14—H14A	0.9700
N4—C13	1.365 (5)	C14—H14B	0.9700
N4—C14	1.456 (5)	C15—C16	1.376 (6)
C1—H1	0.9300	C15—C20	1.378 (6)
C2—C3	1.351 (6)	C16—C17	1.386 (6)
C2—H2	0.9300	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.380 (6)
C4—C5	1.510 (6)	C17—H17	0.9300
C4—H4A	0.9700	C18—C19	1.378 (6)
C4—H4B	0.9700	C18—C18^iii	1.476 (9)
C5—C10	1.374 (6)	C19—C20	1.382 (6)
C5—C6	1.377 (6)	C19—H19	0.9300
C6—C7	1.383 (6)	C20—H20	0.9300
N3^i—Ni1—N3	180.0	C7—C6—H6	119.7
N3^i—Ni1—N1	87.59 (13)	C8—C7—C6	121.8 (4)
N3—Ni1—N1	92.41 (13)	C8—C7—H7	119.1
N3^i—Ni1—N1^i	92.41 (13)	C6—C7—H7	119.1
N3—Ni1—N1^i	87.59 (13)	C7—C8—C9	117.4 (4)
N1—Ni1—N1^i	180.00 (17)	C7—C8—C8^ii	121.8 (4)
N3^i—Ni1—Cl1	90.22 (10)	C9—C8—C8^ii	120.8 (5)
N3—Ni1—Cl1	89.78 (10)	C10—C9—C8	120.3 (5)
N1—Ni1—Cl1	89.69 (10)	C10—C9—H9	119.8
N1^i—Ni1—Cl1	90.31 (10)	C8—C9—H9	119.8
N3^i—Ni1—Cl1^i	89.78 (10)	C5—C10—C9	121.8 (4)
N3—Ni1—Cl1^i	90.22 (10)	C5—C10—H10	119.1
N1—Ni1—Cl1^i	90.31 (10)	C9—C10—H10	119.1
N1^i—Ni1—Cl1^i	89.69 (10)	N3—C11—N4	112.5 (4)
Cl1—Ni1—Cl1^i	180.0	N3—C11—H11	123.8
C1—N1—C3	103.7 (4)	N4—C11—H11	123.8
C1—N1—Ni1	130.8 (3)	C13—C12—N3	110.9 (4)
C3—N1—Ni1	125.5 (3)	C13—C12—H12	124.6
C1—N2—C2	107.0 (4)	N3—C12—H12	124.6
C1—N2—C4	127.1 (4)	C12—C13—N4	105.0 (4)
C2—N2—C4	125.7 (4)	C12—C13—H13	127.5
C11—N3—C12	104.2 (4)	N4—C13—H13	127.5
C11—N3—Ni1	128.3 (3)	N4—C14—C15	111.6 (4)
C12—N3—Ni1	127.4 (3)	N4—C14—H14A	109.3
C11—N4—C13	107.3 (4)	C15—C14—H14A	109.3
C11—N4—C14	125.6 (4)	N4—C14—H14B	109.3
C13—N4—C14	127.1 (4)	C15—C14—H14B	109.3
N1—C1—N2	112.6 (4)	H14A—C14—H14B	108.0
N1—C1—H1	123.7	C16—C15—C20	117.4 (4)
N2—C1—H1	123.7	C16—C15—C14	123.0 (4)
N2—C2—C3	106.0 (4)	C20—C15—C14	119.6 (4)
N2—C2—H2	127.0	C15—C16—C17	122.0 (4)
C3—C2—H2	127.0	C15—C16—H16	119.0
C2—C3—N1	110.8 (4)	C17—C16—H16	119.0
C2—C3—H3	124.6	C18—C17—C16	120.1 (4)
N1—C3—H3	124.6	C18—C17—H17	120.0
N2—C4—C5	110.8 (3)	C16—C17—H17	120.0
N2—C4—H4A	109.5	C19—C18—C17	118.2 (4)
C5—C4—H4A	109.5	C19—C18—C18^iii	120.6 (5)
N2—C4—H4B	109.5	C17—C18—C18^iii	121.2 (5)
C5—C4—H4B	109.5	C18—C19—C20	121.1 (4)
H4A—C4—H4B	108.1	C18—C19—H19	119.4
C10—C5—C6	118.0 (4)	C20—C19—H19	119.4
C10—C5—C4	120.5 (4)	C15—C20—C19	121.1 (4)
C6—C5—C4	121.4 (5)	C15—C20—H20	119.4
C5—C6—C7	120.6 (5)	C19—C20—H20	119.4
C5—C6—H6	119.7
C3—N1—C1—N2	−0.9 (5)	C12—N3—C11—N4	1.7 (5)
Ni1—N1—C1—N2	176.6 (3)	Ni1—N3—C11—N4	178.2 (3)
C2—N2—C1—N1	1.2 (5)	C13—N4—C11—N3	−1.1 (5)
C4—N2—C1—N1	175.8 (4)	C14—N4—C11—N3	179.6 (4)
C1—N2—C2—C3	−0.9 (5)	C11—N3—C12—C13	−1.7 (5)
C4—N2—C2—C3	−175.6 (4)	Ni1—N3—C12—C13	−178.2 (3)
N2—C2—C3—N1	0.4 (6)	N3—C12—C13—N4	1.1 (6)
C1—N1—C3—C2	0.3 (5)	C11—N4—C13—C12	0.0 (5)
Ni1—N1—C3—C2	−177.4 (3)	C14—N4—C13—C12	179.3 (4)
C1—N2—C4—C5	−105.6 (5)	C11—N4—C14—C15	−116.3 (5)
C2—N2—C4—C5	68.0 (6)	C13—N4—C14—C15	64.6 (6)
N2—C4—C5—C10	77.7 (6)	N4—C14—C15—C16	−123.9 (5)
N2—C4—C5—C6	−98.6 (5)	N4—C14—C15—C20	55.2 (5)
C10—C5—C6—C7	−2.6 (7)	C20—C15—C16—C17	0.6 (7)
C4—C5—C6—C7	173.8 (4)	C14—C15—C16—C17	179.7 (4)
C5—C6—C7—C8	0.0 (7)	C15—C16—C17—C18	−1.0 (7)
C6—C7—C8—C9	2.2 (7)	C16—C17—C18—C19	1.2 (7)
C6—C7—C8—C8^ii	−175.6 (3)	C16—C17—C18—C18^iii	−177.3 (3)
C7—C8—C9—C10	−2.0 (7)	C17—C18—C19—C20	−1.0 (7)
C8^ii—C8—C9—C10	175.9 (4)	C18^iii—C18—C19—C20	177.5 (3)
C6—C5—C10—C9	2.8 (7)	C16—C15—C20—C19	−0.4 (7)
C4—C5—C10—C9	−173.6 (4)	C14—C15—C20—C19	−179.5 (4)
C8—C9—C10—C5	−0.5 (8)	C18—C19—C20—C15	0.7 (7)

Symmetry codes: (i) −x+1/2, −y+1/2, −z+1; (ii) −x, y, −z+1/2; (iii) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Cl1^iv	0.93	2.79	3.605 (4)	147
C14—H14B···Cl1^iv	0.97	2.80	3.686 (5)	153

Symmetry code: (iv) −x+1/2, −y+3/2, −z+1.