The crystal structure of bis­[(E)-4-bromo-2-({[2-(pyridin-2-yl)eth­yl]imino}­meth­yl)phenol]nickel(II) bis­[(E)-4-bromo-2-({[2-(pyridin-2-yl)eth­yl]imino}­meth­yl)phenolato]nickel(II) bis(perchlorate) methanol monosolvate, a structure containing strong inter-species hydrogen bonds

The title compound, [Ni(C₁₄H₁₂BrN₂O)₂][Ni(C₁₃H₁₂BrN₂O)₂](ClO₄)₂ 2(MeOH) consists of two mononuclear ([Ni(HL)₂]²⁺ and [NiL₂]) complexes linked by strong hydrogen bonding [O...O separations of only 2.430 (5) Å], which is the shortest reported to date for such species.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.009 Å
• Disorder in main residue
• R factor = 0.061
• wR factor = 0.178
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
            identifier.
            transparent
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low .      0.960 Why?
PLAT234_ALERT_4_C Large Hirshfeld Difference Cl1      --O11              0.16 Ang.
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C4B Check
PLAT244_ALERT_4_C Low    'Solvent' Ueq as Compared to Neighbors of        Cl1 Check
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00905 Ang.
PLAT410_ALERT_2_C Short Intra H...H Contact  H7BA     ..H8BA             1.98 Ang.
PLAT411_ALERT_2_C Short Inter H...H Contact  H12A     ..H9CB             2.03 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14A     ..N1A              2.67 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9BB     ..BR1              3.12 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13C     ..BR1              3.08 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14C     ..BR1              3.05 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     11.149 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.734 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600        256 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         27 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         25 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT012_ALERT_1_G N.O.K.   _shelx_res_checksum Found in CIF ......     Please Check
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large       9.37 Why ?
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          5 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          1 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          2 Report
PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR Records          1 Report
PLAT300_ALERT_4_G Atom Site Occupancy of O1S        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C1S        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H1S        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H1S1       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H1S2       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H1S3       Constrained at        0.5 Check
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        43% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  3  )        80% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  4  )       100% Note
PLAT432_ALERT_2_G Short Inter X...Y Contact  O14      ..C7A              2.99 Ang.
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         23 Note
PLAT721_ALERT_1_G Bond    Calc     0.96000, Rep     0.97000 Dev...       0.01 Ang.
              C8C      -H8CB            1.555   1.555 ........     #   81 Check
PLAT794_ALERT_5_G Tentative Bond Valency for Ni1       (II)      .       2.05 Info
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............        332 Note
PLAT870_ALERT_4_G ALERTS Related to Twinning Effects Suppressed ..          ! Info
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         57 Note
PLAT951_ALERT_5_G Calculated (ThMax) and CIF-Reported Kmax Differ           2 Units
PLAT957_ALERT_1_G Calculated (ThMax) and Actual (FCF) Kmax Differ           2 Units

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

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

---

Computing details

Data collection: APEX3 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/1 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Bis[(E)-4-bromo-2-({[2-(pyridin-2-yl)ethyl]imino}methyl)phenol]nickel(II) bis[(E)-4-bromo-2-({[2-(pyridin-2-yl)ethyl]imino}methyl)phenolato]nickel(II) bis(perchlorate) methanol monosolvate

Crystal data

[Ni(C14H12BrN2O)2][Ni(C14H13BrN2O)2](ClO4)2·CH4O	Dx = 1.642 Mg m^−3
Mr = 1567.04	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbcn	Cell parameters from 4627 reflections
a = 19.103 (5) Å	θ = 2.4–26.3°
b = 17.414 (4) Å	µ = 3.27 mm^−1
c = 19.053 (5) Å	T = 296 K
V = 6339 (3) Å^3	Prism, transparent light olive-green
Z = 4	0.32 × 0.28 × 0.13 mm
F(000) = 3144

Data collection

Bruker APEXII CCD diffractometer	3693 reflections with I > 2σ(I)
w scans	Rint = 0.088
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	θmax = 26.5°, θmin = 1.6°
Tmin = 0.433, Tmax = 0.745	h = −16→23
6170 measured reflections	k = −17→19
6170 independent reflections	l = −22→23

Refinement

Refinement on F^2	332 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.061	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.178	w = 1/[σ^2(Fo^2) + (0.0767P)^2 + 9.3718P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
6170 reflections	Δρmax = 0.90 e Å^−3
492 parameters	Δρmin = −0.89 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. Refined as a two-component twin.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ni1	0.500000	0.55970 (5)	0.250000	0.0426 (3)
Br1	0.87543 (3)	0.64179 (5)	0.18413 (5)	0.0946 (3)
O1A	0.57178 (18)	0.6453 (2)	0.2724 (2)	0.0503 (9)
H1A	0.567 (4)	0.686 (3)	0.294 (4)	0.11 (3)*
N1A	0.5439 (2)	0.5639 (3)	0.1502 (2)	0.0466 (11)
N2A	0.4284 (2)	0.4763 (3)	0.2165 (2)	0.0502 (11)
C1A	0.6398 (3)	0.6417 (3)	0.2536 (3)	0.0478 (12)
C2A	0.6928 (3)	0.6663 (4)	0.2984 (3)	0.0607 (16)
H2AA	0.681286	0.683694	0.343027	0.073*
C3A	0.7625 (3)	0.6653 (4)	0.2778 (4)	0.0636 (17)
H3AA	0.797194	0.682336	0.308245	0.076*
C4A	0.7794 (3)	0.6394 (3)	0.2132 (4)	0.0608 (16)
C5A	0.7296 (3)	0.6124 (3)	0.1678 (3)	0.0581 (15)
H5AA	0.742734	0.593314	0.124161	0.070*
C6A	0.6583 (2)	0.6133 (3)	0.1872 (3)	0.0463 (13)
C7A	0.6069 (3)	0.5853 (3)	0.1373 (3)	0.0532 (14)
H7AA	0.621250	0.582503	0.090759	0.064*
C8A	0.5050 (3)	0.5342 (4)	0.0888 (3)	0.0662 (17)
H8AA	0.520105	0.482112	0.079184	0.079*
H8AB	0.516229	0.565325	0.048055	0.079*
C9A	0.4255 (3)	0.5347 (4)	0.0998 (3)	0.0635 (17)
H9AA	0.411465	0.585451	0.115535	0.076*
H9AB	0.402788	0.525256	0.055118	0.076*
C10A	0.4001 (3)	0.4772 (4)	0.1514 (3)	0.0562 (15)
C11A	0.3483 (4)	0.4241 (4)	0.1335 (4)	0.077 (2)
H11A	0.328428	0.425746	0.088979	0.093*
C12A	0.3262 (4)	0.3696 (5)	0.1806 (5)	0.088 (2)
H12A	0.291893	0.334153	0.168416	0.105*
C13A	0.3560 (4)	0.3686 (4)	0.2461 (4)	0.077 (2)
H13A	0.342541	0.332136	0.279138	0.092*
C14A	0.4063 (3)	0.4225 (4)	0.2620 (3)	0.0647 (17)
H14A	0.426067	0.421569	0.306602	0.078*
Ni2	0.500000	0.85234 (6)	0.250000	0.0536 (3)
Br2	0.45642 (5)	0.75407 (7)	0.62684 (4)	0.1140 (4)
O1B	0.53437 (18)	0.7680 (2)	0.32016 (19)	0.0532 (9)
N1B	0.4042 (2)	0.8375 (3)	0.2999 (3)	0.0628 (14)
C1B	0.5161 (3)	0.7651 (3)	0.3887 (3)	0.0532 (14)
C2B	0.5638 (3)	0.7434 (4)	0.4396 (3)	0.0689 (18)
H2BA	0.609303	0.731075	0.426250	0.083*
C3B	0.5457 (4)	0.7395 (4)	0.5095 (4)	0.0718 (18)
H3BA	0.578777	0.725434	0.542938	0.086*
C4B	0.4787 (3)	0.7565 (4)	0.5292 (3)	0.0694 (19)
C5B	0.4306 (3)	0.7773 (4)	0.4815 (4)	0.0682 (18)
H5BA	0.385214	0.788122	0.496166	0.082*
C6B	0.4474 (3)	0.7833 (3)	0.4096 (3)	0.0577 (15)
C7B	0.3934 (3)	0.8077 (4)	0.3602 (4)	0.0672 (18)
H7BA	0.347101	0.800911	0.373764	0.081*
C8B	0.3418 (7)	0.8540 (6)	0.2606 (6)	0.072 (3)	0.750 (8)
H8BA	0.300765	0.841264	0.288191	0.087*	0.750 (8)
H8BB	0.340919	0.823569	0.217958	0.087*	0.750 (8)
C9B	0.3412 (5)	0.9387 (5)	0.2424 (5)	0.078 (2)	0.750 (8)
H9BA	0.293708	0.953252	0.230515	0.094*	0.750 (8)
H9BB	0.354464	0.967433	0.283973	0.094*	0.750 (8)
N2B	0.4574 (3)	0.9393 (4)	0.1842 (4)	0.0778 (18)	0.750 (8)
C10B	0.3876 (3)	0.9618 (4)	0.1844 (4)	0.081 (2)	0.750 (8)
C11B	0.3634 (3)	1.0139 (4)	0.1347 (5)	0.094 (2)	0.750 (8)
H11B	0.316734	1.028997	0.134862	0.113*	0.750 (8)
C12B	0.4091 (4)	1.0436 (4)	0.0848 (4)	0.104 (3)	0.750 (8)
H12B	0.393009	1.078435	0.051579	0.125*	0.750 (8)
C13B	0.4790 (4)	1.0211 (5)	0.0846 (4)	0.104 (3)	0.750 (8)
H13B	0.509529	1.040883	0.051222	0.125*	0.750 (8)
C14B	0.5031 (3)	0.9689 (5)	0.1343 (4)	0.087 (2)	0.750 (8)
H14B	0.549774	0.953894	0.134149	0.105*	0.750 (8)
C8C	0.340 (2)	0.877 (3)	0.2588 (15)	0.075 (4)	0.250 (8)
H8CA	0.298029	0.848864	0.270933	0.090*	0.250 (8)
H8CB	0.335150	0.928550	0.276206	0.090*	0.250 (8)
C9C	0.3451 (12)	0.8802 (13)	0.1796 (12)	0.078 (3)	0.250 (8)
H9CA	0.356268	0.829295	0.162178	0.094*	0.250 (8)
H9CB	0.299344	0.893832	0.161295	0.094*	0.250 (8)
N2C	0.4645 (9)	0.9346 (14)	0.1779 (12)	0.082 (3)	0.250 (8)
C10C	0.3968 (8)	0.9346 (12)	0.1512 (12)	0.086 (3)	0.250 (8)
C11C	0.3795 (10)	0.9826 (13)	0.0956 (13)	0.094 (3)	0.250 (8)
H11C	0.334160	0.982612	0.077782	0.112*	0.250 (8)
C12C	0.4299 (13)	1.0306 (13)	0.0666 (12)	0.101 (3)	0.250 (8)
H12C	0.418312	1.062737	0.029362	0.121*	0.250 (8)
C13C	0.4976 (12)	1.0306 (15)	0.0932 (15)	0.099 (3)	0.250 (8)
H13C	0.531373	1.062758	0.073817	0.119*	0.250 (8)
C14C	0.5150 (9)	0.9826 (16)	0.1489 (15)	0.090 (3)	0.250 (8)
H14C	0.560283	0.982653	0.166693	0.109*	0.250 (8)
Cl1	0.73020 (12)	0.41261 (15)	0.04156 (12)	0.1002 (7)
O11	0.7917 (4)	0.4471 (5)	0.0653 (5)	0.145 (4)	0.602 (8)
O12	0.7358 (6)	0.3960 (6)	−0.0303 (3)	0.135 (4)	0.602 (8)
O13	0.7219 (5)	0.3417 (5)	0.0779 (5)	0.145 (4)	0.602 (8)
O14	0.6721 (5)	0.4583 (6)	0.0544 (6)	0.179 (5)	0.602 (8)
O11A	0.7786 (8)	0.4212 (8)	0.0960 (7)	0.157 (6)	0.398 (8)
O12A	0.6654 (5)	0.3894 (10)	0.0683 (9)	0.175 (6)	0.398 (8)
O13A	0.7546 (9)	0.3604 (8)	−0.0080 (7)	0.156 (6)	0.398 (8)
O14A	0.7209 (8)	0.4854 (5)	0.0090 (7)	0.133 (5)	0.398 (8)
O1S	0.7449 (6)	0.2322 (7)	−0.0582 (6)	0.094 (3)	0.5
H1S	0.739358	0.275191	−0.041527	0.141*	0.5
C1S	0.7385 (9)	0.1792 (10)	−0.0070 (8)	0.098 (5)	0.5
H1S1	0.783439	0.156617	0.002282	0.146*	0.5
H1S2	0.706437	0.139927	−0.021727	0.146*	0.5
H1S3	0.721208	0.203222	0.034875	0.146*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0392 (5)	0.0488 (6)	0.0399 (5)	0.000	0.0026 (4)	0.000
Br1	0.0406 (3)	0.1081 (7)	0.1351 (7)	−0.0032 (4)	0.0209 (4)	−0.0139 (5)
O1A	0.0375 (18)	0.055 (3)	0.058 (2)	−0.0020 (18)	0.0072 (16)	−0.018 (2)
N1A	0.046 (2)	0.054 (3)	0.039 (2)	0.001 (2)	0.0004 (18)	−0.002 (2)
N2A	0.049 (2)	0.049 (3)	0.053 (3)	−0.004 (2)	0.003 (2)	0.000 (2)
C1A	0.038 (3)	0.046 (3)	0.060 (3)	0.001 (2)	0.003 (2)	0.002 (3)
C2A	0.048 (3)	0.067 (4)	0.067 (4)	−0.002 (3)	−0.003 (3)	−0.016 (3)
C3A	0.044 (3)	0.058 (4)	0.089 (5)	0.000 (3)	−0.006 (3)	−0.017 (3)
C4A	0.039 (3)	0.052 (4)	0.092 (5)	0.002 (3)	0.015 (3)	−0.004 (3)
C5A	0.044 (3)	0.060 (4)	0.071 (4)	0.003 (3)	0.018 (3)	−0.004 (3)
C6A	0.038 (3)	0.051 (3)	0.050 (3)	0.003 (2)	0.007 (2)	0.000 (3)
C7A	0.052 (3)	0.064 (4)	0.043 (3)	0.003 (3)	0.010 (2)	−0.001 (3)
C8A	0.059 (3)	0.095 (5)	0.044 (3)	−0.010 (3)	0.000 (3)	−0.014 (3)
C9A	0.050 (3)	0.091 (5)	0.050 (3)	−0.004 (3)	−0.009 (3)	−0.013 (3)
C10A	0.044 (3)	0.062 (4)	0.063 (4)	0.003 (3)	−0.003 (3)	−0.006 (3)
C11A	0.068 (4)	0.084 (5)	0.080 (5)	−0.010 (4)	−0.004 (4)	−0.022 (4)
C12A	0.074 (5)	0.077 (6)	0.113 (7)	−0.017 (4)	0.003 (4)	−0.020 (5)
C13A	0.070 (4)	0.056 (4)	0.104 (6)	−0.013 (3)	0.024 (4)	−0.006 (4)
C14A	0.059 (4)	0.062 (4)	0.073 (4)	0.005 (3)	0.012 (3)	−0.003 (3)
Ni2	0.0385 (5)	0.0453 (6)	0.0770 (7)	0.000	−0.0050 (5)	0.000
Br2	0.0980 (6)	0.1772 (11)	0.0669 (5)	−0.0334 (6)	0.0250 (4)	0.0002 (5)
O1B	0.051 (2)	0.053 (2)	0.055 (2)	0.0138 (18)	0.0065 (17)	−0.0076 (18)
N1B	0.039 (2)	0.079 (4)	0.070 (3)	0.009 (2)	−0.001 (2)	−0.016 (3)
C1B	0.054 (3)	0.049 (4)	0.057 (3)	0.005 (3)	0.005 (3)	−0.008 (3)
C2B	0.060 (4)	0.082 (5)	0.065 (4)	0.018 (3)	0.009 (3)	−0.006 (3)
C3B	0.072 (4)	0.078 (5)	0.066 (4)	0.007 (4)	0.003 (3)	−0.007 (4)
C4B	0.065 (4)	0.082 (5)	0.060 (4)	−0.024 (4)	0.011 (3)	−0.010 (3)
C5B	0.051 (3)	0.077 (5)	0.077 (4)	−0.012 (3)	0.019 (3)	−0.018 (4)
C6B	0.044 (3)	0.056 (4)	0.074 (4)	−0.006 (3)	0.010 (3)	−0.016 (3)
C7B	0.038 (3)	0.076 (5)	0.087 (5)	0.002 (3)	0.005 (3)	−0.030 (4)
C8B	0.048 (4)	0.066 (6)	0.103 (5)	0.007 (5)	−0.007 (4)	−0.011 (4)
C9B	0.058 (4)	0.069 (5)	0.108 (5)	0.008 (4)	−0.015 (4)	−0.007 (4)
N2B	0.070 (4)	0.052 (4)	0.111 (4)	−0.006 (3)	−0.028 (3)	0.011 (3)
C10B	0.071 (4)	0.058 (4)	0.114 (4)	0.007 (3)	−0.025 (4)	0.008 (4)
C11B	0.083 (5)	0.071 (5)	0.128 (5)	0.015 (4)	−0.026 (4)	0.019 (4)
C12B	0.098 (5)	0.081 (5)	0.133 (5)	0.014 (4)	−0.029 (4)	0.028 (4)
C13B	0.101 (5)	0.080 (5)	0.132 (5)	−0.009 (4)	−0.030 (5)	0.028 (4)
C14B	0.083 (4)	0.062 (4)	0.117 (5)	−0.008 (4)	−0.035 (4)	0.023 (4)
C8C	0.052 (6)	0.067 (8)	0.105 (6)	0.010 (7)	−0.013 (6)	−0.009 (7)
C9C	0.059 (5)	0.066 (6)	0.109 (5)	0.010 (5)	−0.017 (5)	−0.002 (5)
N2C	0.074 (5)	0.057 (5)	0.114 (5)	−0.002 (5)	−0.029 (5)	0.012 (5)
C10C	0.075 (5)	0.064 (5)	0.118 (5)	0.006 (5)	−0.023 (5)	0.011 (5)
C11C	0.084 (5)	0.072 (5)	0.126 (6)	0.010 (5)	−0.027 (5)	0.018 (5)
C12C	0.093 (6)	0.078 (5)	0.132 (6)	0.009 (5)	−0.028 (5)	0.026 (5)
C13C	0.095 (6)	0.074 (5)	0.128 (6)	−0.003 (5)	−0.033 (5)	0.025 (5)
C14C	0.087 (5)	0.064 (5)	0.120 (6)	−0.007 (5)	−0.031 (5)	0.020 (5)
Cl1	0.0979 (15)	0.1148 (19)	0.0879 (14)	0.0206 (14)	−0.0121 (11)	−0.0020 (13)
O11	0.159 (9)	0.137 (9)	0.141 (9)	−0.016 (7)	−0.045 (8)	0.059 (7)
O12	0.181 (10)	0.139 (10)	0.085 (7)	0.047 (8)	0.013 (7)	−0.004 (6)
O13	0.103 (7)	0.175 (10)	0.158 (8)	−0.006 (7)	−0.017 (7)	0.044 (8)
O14	0.167 (10)	0.213 (12)	0.157 (10)	0.109 (10)	−0.025 (8)	−0.031 (10)
O11A	0.169 (11)	0.147 (12)	0.154 (12)	−0.003 (10)	−0.093 (10)	0.062 (10)
O12A	0.156 (12)	0.200 (15)	0.168 (12)	0.000 (12)	0.051 (11)	0.028 (13)
O13A	0.175 (12)	0.157 (13)	0.137 (12)	0.063 (11)	0.015 (11)	−0.008 (11)
O14A	0.141 (10)	0.149 (10)	0.108 (9)	0.035 (9)	−0.020 (8)	0.034 (9)
O1S	0.091 (7)	0.098 (8)	0.093 (7)	0.033 (7)	0.005 (6)	−0.012 (7)
C1S	0.120 (11)	0.089 (10)	0.084 (9)	0.068 (9)	0.015 (8)	0.019 (8)

Geometric parameters (Å, º)

Ni1—O1A	2.070 (4)	C2B—H2BA	0.9300
Ni1—O1A^i	2.070 (4)	C3B—C4B	1.367 (9)
Ni1—N1A	2.080 (4)	C3B—H3BA	0.9300
Ni1—N1A^i	2.080 (4)	C4B—C5B	1.342 (9)
Ni1—N2A	2.095 (5)	C5B—C6B	1.411 (9)
Ni1—N2A^i	2.095 (5)	C5B—H5BA	0.9300
Br1—C4A	1.917 (5)	C6B—C7B	1.459 (9)
O1A—C1A	1.349 (6)	C7B—H7BA	0.9300
O1A—H1A	0.82 (2)	C8B—C9B	1.514 (14)
N1A—C7A	1.283 (6)	C8B—H8BA	0.9700
N1A—C8A	1.480 (7)	C8B—H8BB	0.9700
N2A—C14A	1.344 (7)	C9B—C10B	1.472 (11)
N2A—C10A	1.353 (7)	C9B—H9BA	0.9700
C1A—C2A	1.391 (8)	C9B—H9BB	0.9700
C1A—C6A	1.404 (7)	N2B—C10B	1.3900
C2A—C3A	1.387 (8)	N2B—C14B	1.3900
C2A—H2AA	0.9300	C10B—C11B	1.3900
C3A—C4A	1.350 (9)	C11B—C12B	1.3900
C3A—H3AA	0.9300	C11B—H11B	0.9300
C4A—C5A	1.370 (9)	C12B—C13B	1.3900
C5A—C6A	1.411 (7)	C12B—H12B	0.9300
C5A—H5AA	0.9300	C13B—C14B	1.3900
C6A—C7A	1.451 (7)	C13B—H13B	0.9300
C7A—H7AA	0.9300	C14B—H14B	0.9300
C8A—C9A	1.534 (8)	C8C—C9C	1.513 (15)
C8A—H8AA	0.9700	C8C—H8CA	0.9700
C8A—H8AB	0.9700	C8C—H8CB	0.9700
C9A—C10A	1.485 (9)	C9C—C10C	1.472 (11)
C9A—H9AA	0.9700	C9C—H9CA	0.9700
C9A—H9AB	0.9700	C9C—H9CB	0.9700
C10A—C11A	1.396 (9)	N2C—C10C	1.3900
C11A—C12A	1.373 (10)	N2C—C14C	1.3900
C11A—H11A	0.9300	C10C—C11C	1.3900
C12A—C13A	1.371 (11)	C11C—C12C	1.3900
C12A—H12A	0.9300	C11C—H11C	0.9300
C13A—C14A	1.377 (9)	C12C—C13C	1.3900
C13A—H13A	0.9300	C12C—H12C	0.9300
C14A—H14A	0.9300	C13C—C14C	1.3900
Ni2—N1B	2.079 (5)	C13C—H13C	0.9300
Ni2—N1B^i	2.079 (5)	C14C—H14C	0.9300
Ni2—O1B^i	2.091 (4)	Cl1—O14	1.387 (6)
Ni2—O1B	2.091 (4)	Cl1—O13A	1.391 (6)
Ni2—N2C	2.098 (18)	Cl1—O11	1.396 (6)
Ni2—N2C^i	2.098 (18)	Cl1—O11A	1.397 (6)
Ni2—N2B^i	2.128 (6)	Cl1—O12A	1.399 (6)
Ni2—N2B	2.128 (6)	Cl1—O12	1.403 (6)
Br2—C4B	1.909 (6)	Cl1—O14A	1.422 (6)
O1B—C1B	1.353 (7)	Cl1—O13	1.424 (6)
N1B—C7B	1.277 (8)	O1S—C1S	1.349 (17)
N1B—C8B	1.436 (14)	O1S—H1S	0.8200
N1B—C8C	1.60 (5)	C1S—H1S1	0.9600
C1B—C2B	1.383 (9)	C1S—H1S2	0.9600
C1B—C6B	1.409 (8)	C1S—H1S3	0.9600
C2B—C3B	1.378 (9)
O1A—Ni1—O1A^i	87.8 (2)	C8C—N1B—Ni2	113.2 (10)
O1A—Ni1—N1A	84.01 (16)	O1B—C1B—C2B	121.2 (5)
O1A^i—Ni1—N1A	93.07 (16)	O1B—C1B—C6B	120.2 (5)
O1A—Ni1—N1A^i	93.07 (16)	C2B—C1B—C6B	118.6 (6)
O1A^i—Ni1—N1A^i	84.01 (16)	C3B—C2B—C1B	121.7 (6)
N1A—Ni1—N1A^i	176.0 (2)	C3B—C2B—H2BA	119.2
O1A—Ni1—N2A	174.13 (17)	C1B—C2B—H2BA	119.2
O1A^i—Ni1—N2A	90.23 (17)	C4B—C3B—C2B	119.3 (7)
N1A—Ni1—N2A	90.56 (17)	C4B—C3B—H3BA	120.3
N1A^i—Ni1—N2A	92.25 (17)	C2B—C3B—H3BA	120.3
O1A—Ni1—N2A^i	90.23 (17)	C5B—C4B—C3B	120.9 (6)
O1A^i—Ni1—N2A^i	174.13 (17)	C5B—C4B—Br2	120.9 (5)
N1A—Ni1—N2A^i	92.25 (17)	C3B—C4B—Br2	118.1 (5)
N1A^i—Ni1—N2A^i	90.56 (17)	C4B—C5B—C6B	121.5 (6)
N2A—Ni1—N2A^i	92.2 (3)	C4B—C5B—H5BA	119.3
C1A—O1A—Ni1	123.4 (3)	C6B—C5B—H5BA	119.3
C1A—O1A—H1A	107 (6)	C1B—C6B—C5B	118.0 (6)
Ni1—O1A—H1A	130 (6)	C1B—C6B—C7B	122.8 (6)
C7A—N1A—C8A	115.0 (4)	C5B—C6B—C7B	119.2 (5)
C7A—N1A—Ni1	124.3 (4)	N1B—C7B—C6B	125.8 (5)
C8A—N1A—Ni1	120.5 (3)	N1B—C7B—H7BA	117.1
C14A—N2A—C10A	118.3 (5)	C6B—C7B—H7BA	117.1
C14A—N2A—Ni1	119.5 (4)	N1B—C8B—C9B	108.6 (9)
C10A—N2A—Ni1	122.1 (4)	N1B—C8B—H8BA	110.0
O1A—C1A—C2A	121.6 (5)	C9B—C8B—H8BA	110.0
O1A—C1A—C6A	119.9 (5)	N1B—C8B—H8BB	110.0
C2A—C1A—C6A	118.5 (5)	C9B—C8B—H8BB	110.0
C3A—C2A—C1A	121.4 (6)	H8BA—C8B—H8BB	108.3
C3A—C2A—H2AA	119.3	C10B—C9B—C8B	115.7 (8)
C1A—C2A—H2AA	119.3	C10B—C9B—H9BA	108.4
C4A—C3A—C2A	119.4 (6)	C8B—C9B—H9BA	108.4
C4A—C3A—H3AA	120.3	C10B—C9B—H9BB	108.4
C2A—C3A—H3AA	120.3	C8B—C9B—H9BB	108.4
C3A—C4A—C5A	121.6 (5)	H9BA—C9B—H9BB	107.4
C3A—C4A—Br1	119.1 (5)	C10B—N2B—C14B	120.0
C5A—C4A—Br1	119.3 (5)	C10B—N2B—Ni2	124.5 (3)
C4A—C5A—C6A	120.1 (5)	C14B—N2B—Ni2	115.3 (3)
C4A—C5A—H5AA	120.0	C11B—C10B—N2B	120.0
C6A—C5A—H5AA	120.0	C11B—C10B—C9B	119.4 (5)
C1A—C6A—C5A	118.9 (5)	N2B—C10B—C9B	120.1 (5)
C1A—C6A—C7A	122.6 (4)	C10B—C11B—C12B	120.0
C5A—C6A—C7A	118.5 (5)	C10B—C11B—H11B	120.0
N1A—C7A—C6A	127.4 (5)	C12B—C11B—H11B	120.0
N1A—C7A—H7AA	116.3	C13B—C12B—C11B	120.0
C6A—C7A—H7AA	116.3	C13B—C12B—H12B	120.0
N1A—C8A—C9A	112.8 (5)	C11B—C12B—H12B	120.0
N1A—C8A—H8AA	109.0	C12B—C13B—C14B	120.0
C9A—C8A—H8AA	109.0	C12B—C13B—H13B	120.0
N1A—C8A—H8AB	109.0	C14B—C13B—H13B	120.0
C9A—C8A—H8AB	109.0	C13B—C14B—N2B	120.0
H8AA—C8A—H8AB	107.8	C13B—C14B—H14B	120.0
C10A—C9A—C8A	114.2 (5)	N2B—C14B—H14B	120.0
C10A—C9A—H9AA	108.7	C9C—C8C—N1B	117 (3)
C8A—C9A—H9AA	108.7	C9C—C8C—H8CA	107.9
C10A—C9A—H9AB	108.7	N1B—C8C—H8CA	107.9
C8A—C9A—H9AB	108.7	C9C—C8C—H8CB	107.9
H9AA—C9A—H9AB	107.6	N1B—C8C—H8CB	107.9
N2A—C10A—C11A	120.0 (6)	H8CA—C8C—H8CB	107.2
N2A—C10A—C9A	119.0 (5)	C10C—C9C—C8C	115.6 (11)
C11A—C10A—C9A	121.1 (6)	C10C—C9C—H9CA	108.4
C12A—C11A—C10A	121.0 (7)	C8C—C9C—H9CA	108.4
C12A—C11A—H11A	119.5	C10C—C9C—H9CB	108.4
C10A—C11A—H11A	119.5	C8C—C9C—H9CB	108.4
C13A—C12A—C11A	118.4 (7)	H9CA—C9C—H9CB	107.4
C13A—C12A—H12A	120.8	C10C—N2C—C14C	120.0
C11A—C12A—H12A	120.8	C10C—N2C—Ni2	122.7 (9)
C12A—C13A—C14A	118.8 (7)	C14C—N2C—Ni2	116.6 (9)
C12A—C13A—H13A	120.6	C11C—C10C—N2C	120.0
C14A—C13A—H13A	120.6	C11C—C10C—C9C	120.5 (7)
N2A—C14A—C13A	123.5 (7)	N2C—C10C—C9C	119.4 (7)
N2A—C14A—H14A	118.2	C10C—C11C—C12C	120.0
C13A—C14A—H14A	118.2	C10C—C11C—H11C	120.0
N1B—Ni2—N1B^i	165.8 (3)	C12C—C11C—H11C	120.0
N1B—Ni2—O1B^i	85.91 (17)	C13C—C12C—C11C	120.0
N1B^i—Ni2—O1B^i	84.10 (18)	C13C—C12C—H12C	120.0
N1B—Ni2—O1B	84.10 (18)	C11C—C12C—H12C	120.0
N1B^i—Ni2—O1B	85.91 (17)	C12C—C13C—C14C	120.0
O1B^i—Ni2—O1B	90.8 (2)	C12C—C13C—H13C	120.0
N1B—Ni2—N2C	95.7 (6)	C14C—C13C—H13C	120.0
N1B^i—Ni2—N2C	94.0 (6)	C13C—C14C—N2C	120.0
O1B^i—Ni2—N2C	87.7 (7)	C13C—C14C—H14C	120.0
O1B—Ni2—N2C	178.5 (7)	N2C—C14C—H14C	120.0
N1B—Ni2—N2C^i	94.0 (6)	O14—Cl1—O11	111.7 (4)
N1B^i—Ni2—N2C^i	95.7 (6)	O13A—Cl1—O11A	110.6 (4)
O1B^i—Ni2—N2C^i	178.5 (7)	O13A—Cl1—O12A	110.8 (4)
O1B—Ni2—N2C^i	87.7 (7)	O11A—Cl1—O12A	110.2 (4)
N2C—Ni2—N2C^i	93.8 (14)	O14—Cl1—O12	110.6 (4)
N1B—Ni2—N2B^i	99.0 (2)	O11—Cl1—O12	109.9 (4)
N1B^i—Ni2—N2B^i	91.2 (2)	O13A—Cl1—O14A	109.1 (4)
O1B^i—Ni2—N2B^i	175.1 (2)	O11A—Cl1—O14A	108.1 (4)
O1B—Ni2—N2B^i	90.2 (2)	O12A—Cl1—O14A	107.8 (4)
N1B—Ni2—N2B	91.2 (2)	O14—Cl1—O13	108.8 (4)
N1B^i—Ni2—N2B	99.0 (2)	O11—Cl1—O13	108.0 (4)
O1B^i—Ni2—N2B	90.2 (2)	O12—Cl1—O13	107.7 (4)
O1B—Ni2—N2B	175.1 (2)	C1S—O1S—H1S	109.5
N2B^i—Ni2—N2B	89.3 (4)	O1S—C1S—H1S1	109.5
C1B—O1B—Ni2	124.3 (3)	O1S—C1S—H1S2	109.5
C7B—N1B—C8B	114.7 (6)	H1S1—C1S—H1S2	109.5
C7B—N1B—C8C	119.4 (10)	O1S—C1S—H1S3	109.5
C7B—N1B—Ni2	127.1 (4)	H1S1—C1S—H1S3	109.5
C8B—N1B—Ni2	117.9 (6)	H1S2—C1S—H1S3	109.5
Ni1—O1A—C1A—C2A	−139.6 (5)	O1B—C1B—C6B—C5B	178.3 (5)
Ni1—O1A—C1A—C6A	41.1 (7)	C2B—C1B—C6B—C5B	−0.8 (9)
O1A—C1A—C2A—C3A	−177.4 (6)	O1B—C1B—C6B—C7B	−1.6 (9)
C6A—C1A—C2A—C3A	2.0 (9)	C2B—C1B—C6B—C7B	179.3 (6)
C1A—C2A—C3A—C4A	−0.6 (10)	C4B—C5B—C6B—C1B	1.3 (9)
C2A—C3A—C4A—C5A	−1.5 (10)	C4B—C5B—C6B—C7B	−178.8 (6)
C2A—C3A—C4A—Br1	177.8 (5)	C8B—N1B—C7B—C6B	178.0 (8)
C3A—C4A—C5A—C6A	2.1 (10)	C8C—N1B—C7B—C6B	−168 (2)
Br1—C4A—C5A—C6A	−177.2 (4)	Ni2—N1B—C7B—C6B	5.5 (10)
O1A—C1A—C6A—C5A	178.0 (5)	C1B—C6B—C7B—N1B	−22.5 (10)
C2A—C1A—C6A—C5A	−1.4 (8)	C5B—C6B—C7B—N1B	157.6 (6)
O1A—C1A—C6A—C7A	−1.6 (8)	C7B—N1B—C8B—C9B	122.8 (8)
C2A—C1A—C6A—C7A	179.0 (6)	Ni2—N1B—C8B—C9B	−63.9 (10)
C4A—C5A—C6A—C1A	−0.6 (9)	N1B—C8B—C9B—C10B	77.1 (10)
C4A—C5A—C6A—C7A	179.1 (6)	C14B—N2B—C10B—C11B	0.0
C8A—N1A—C7A—C6A	−177.0 (6)	Ni2—N2B—C10B—C11B	−173.8 (6)
Ni1—N1A—C7A—C6A	−2.9 (9)	C14B—N2B—C10B—C9B	−172.0 (8)
C1A—C6A—C7A—N1A	−19.0 (9)	Ni2—N2B—C10B—C9B	14.3 (8)
C5A—C6A—C7A—N1A	161.4 (6)	C8B—C9B—C10B—C11B	137.7 (8)
C7A—N1A—C8A—C9A	−160.9 (6)	C8B—C9B—C10B—N2B	−50.3 (11)
Ni1—N1A—C8A—C9A	24.7 (7)	N2B—C10B—C11B—C12B	0.0
N1A—C8A—C9A—C10A	−70.4 (7)	C9B—C10B—C11B—C12B	172.0 (8)
C14A—N2A—C10A—C11A	1.4 (8)	C10B—C11B—C12B—C13B	0.0
Ni1—N2A—C10A—C11A	−174.7 (5)	C11B—C12B—C13B—C14B	0.0
C14A—N2A—C10A—C9A	−178.1 (5)	C12B—C13B—C14B—N2B	0.0
Ni1—N2A—C10A—C9A	5.7 (7)	C10B—N2B—C14B—C13B	0.0
C8A—C9A—C10A—N2A	54.1 (7)	Ni2—N2B—C14B—C13B	174.3 (5)
C8A—C9A—C10A—C11A	−125.5 (6)	C7B—N1B—C8C—C9C	−154.4 (15)
N2A—C10A—C11A—C12A	−1.3 (10)	Ni2—N1B—C8C—C9C	32 (3)
C9A—C10A—C11A—C12A	178.2 (6)	N1B—C8C—C9C—C10C	−71 (3)
C10A—C11A—C12A—C13A	0.4 (11)	C14C—N2C—C10C—C11C	0.0
C11A—C12A—C13A—C14A	0.5 (11)	Ni2—N2C—C10C—C11C	−169.7 (19)
C10A—N2A—C14A—C13A	−0.6 (9)	C14C—N2C—C10C—C9C	176 (2)
Ni1—N2A—C14A—C13A	175.6 (5)	Ni2—N2C—C10C—C9C	7 (3)
C12A—C13A—C14A—N2A	−0.4 (10)	C8C—C9C—C10C—C11C	−135 (3)
Ni2—O1B—C1B—C2B	−141.8 (5)	C8C—C9C—C10C—N2C	48 (4)
Ni2—O1B—C1B—C6B	39.1 (7)	N2C—C10C—C11C—C12C	0.0
O1B—C1B—C2B—C3B	−179.4 (6)	C9C—C10C—C11C—C12C	−176 (2)
C6B—C1B—C2B—C3B	−0.2 (10)	C10C—C11C—C12C—C13C	0.0
C1B—C2B—C3B—C4B	0.9 (11)	C11C—C12C—C13C—C14C	0.0
C2B—C3B—C4B—C5B	−0.5 (11)	C12C—C13C—C14C—N2C	0.0
C2B—C3B—C4B—Br2	−177.7 (5)	C10C—N2C—C14C—C13C	0.0
C3B—C4B—C5B—C6B	−0.6 (10)	Ni2—N2C—C14C—C13C	170.3 (18)
Br2—C4B—C5B—C6B	176.6 (5)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O1B	0.82 (2)	1.64 (3)	2.430 (5)	161 (8)
C7A—H7AA···O14	0.93	2.47	2.990 (9)	115
C9A—H9AA···O1A^i	0.97	2.40	3.105 (7)	129
C9A—H9AB···O14^ii	0.97	2.55	3.482 (12)	162
C11A—H11A···O14A^ii	0.93	2.60	3.406 (12)	145
C14A—H14A···N1A^i	0.93	2.67	3.126 (8)	111
C7B—H7BA···O11A^iii	0.93	2.54	3.069 (14)	117
C9B—H9BB···Br1^iii	0.97	3.12	3.859 (10)	134
C14B—H14B···N1B^i	0.93	2.54	3.155 (9)	124
C9C—H9CA···O1B^i	0.97	2.37	3.02 (3)	124
C13C—H13C···Br1^iv	0.93	3.08	3.55 (2)	114
C14C—H14C···Br1^iv	0.93	3.05	3.54 (2)	115
O1S—H1S···O12	0.82	2.12	2.907 (15)	162
O1S—H1S···O13	0.82	2.57	3.249 (15)	140
O1S—H1S···O13A	0.82	1.64	2.436 (16)	162
C1S—H1S3···O13	0.96	2.55	3.276 (19)	133

Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+1, −y+1, −z; (iii) x−1/2, y+1/2, −z+1/2; (iv) −x+3/2, y+1/2, z.