Bis­(benzyl­tri­methyl­ammonium) tetra­chloro­nickelate(II) N-methyl­pyrrolidin-2-one solvate

The title compound, (C₁₀H₁₆N)₂[NiCl₄]·C₅H₉NO, was obtained as a side-product in a reaction of PhNiCl(PPh₃)₂ with quaternary ammonium ions in N-methyl­pyrrolidin-2-one. C—H...Cl interactions link the ions into two-dimensional networks parallel to the bc plane.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.014 Å
• R factor = 0.069
• wR factor = 0.182
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      24.24 Deg.

Author Response:

 The available crystals of the title compound diffracted very weakly,
 especially at higher diffraction angles. This is most likely related
 to the disorder in the solvent molecule and the fact that the crystals
 are thin plates, which contain only a limited amount of matter (see
 also our response to _vrf_PLAT063_I). Data were collected in shells of
 increasing diffraction angle. In the shell with 0.52 < sin\q/\l < 0.55
 [i.e. 21.7 < \q < 23.0 deg] 24.6% of the reflections had an intensity
 of at least twice its standard uncertainty. In the next shell, with
 0.55 < sin\q/\l < 0.58, [i.e. 23.0 < \q < 24.3 deg] only 13.6% of the
 reflections had an intensity above this level. Data collection was
 therefore terminated after finishing this shell.

 Validation issues a number of other alerts which are related to this
 issue:
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
             Calculated sin(theta_max)/wavelength =    0.5777;
PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6]..... 24.24 Deg.;
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....   48 Perc.;
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......
 0.98.

PLAT063_ALERT_3_A Crystal Probably too Large for Beam Size .......       1.25 mm

Author Response:

 Crystals of the title compound are very thin plates, which diffracted
 weakly (see also _vrf_PLAT027_I). A large crystal was used in order to
 gain some intensity. The diffractometer, using \b-filtered MoK\a
 radiation, was equipped with a wide collimator (approximately 2 mm) to
 ensure that the whole crystal was irradiated by the homogenous part of
 the X-ray beam. The vertical aperture at the point detector was set to
 6 mm, the horizontal aperture to 3.81 mm. With these settings, the
 detector receives the diffracted beam without cutting off any edges.

 This alert is related to the following level B alert, which was also
 issued during validation:
CRYSS02_ALERT_3_B  The value of _exptl_crystal_size_max is > 1.0
    Maximum crystal size given =   1.250


Alert level B
CRYSS02_ALERT_3_B  The value of _exptl_crystal_size_max is > 1.0
   Maximum crystal size given =   1.250
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) .......          3

Alert level C
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5777
PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6].....      24.24 Deg.
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         48 Perc.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors  for        C21
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         N1
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         N2
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for        C16
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         N3
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for        Ni1
PLAT301_ALERT_3_C Main Residue  Disorder .........................       8.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         14

   2 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  13 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 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
   9 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: locally modified CAD-4 Software (Enraf-Nonius, 1989); cell refinement: SET4 (de Boer & Duisenberg, 1984); data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS86 (Sheldrick, 1986); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Bis(benzyltrimethylammonium) tetrachloronickel(II) N-methylpyrrolidin-2-one solvate

Crystal data

(C10H16N)2[NiCl4]·C5H9NO	F(000) = 1264
Mr = 600.10	Least Squares Treatment of 25 SET4 (de Boer & Duisenberg, 1984) setting angles.
Monoclinic, P21/c	Dx = 1.307 Mg m^−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 18.5787 (10) Å	Cell parameters from 25 reflections
b = 9.4933 (15) Å	θ = 5.9–12.7°
c = 17.3172 (15) Å	µ = 1.01 mm^−1
β = 93.112 (6)°	T = 298 K
V = 3049.8 (6) Å^3	Plate, blue
Z = 4	1.25 × 0.27 × 0.05 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	2302 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.052
Graphite monochromator	θmax = 24.2°, θmin = 2.2°
ω/2θ scans with Δω = 0.81 + 0.35 tanθ (°)	h = −21→0
Absorption correction: analytical (de Meulenaer & Tompa, 1965)	k = −10→0
Tmin = 0.753, Tmax = 0.951	l = −19→20
4986 measured reflections	3 standard reflections every 60 min
4812 independent reflections	intensity decay: 2.3%

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.182	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0815P)^2] where P = (Fo^2 + 2Fc^2)/3
4812 reflections	(Δ/σ)max < 0.001
309 parameters	Δρmax = 0.69 e Å^−3
4 restraints	Δρmin = −0.36 e Å^−3

Special details

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 e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F^{2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F}2, conventional R-factors R are based on F, with F set to zero for negative F^{2. The observed criterion of F}2 > σ(F^{2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F}2 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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.0292 (3)	0.2659 (7)	0.3999 (3)	0.046 (2)
C1	0.1267 (4)	0.3606 (8)	0.2490 (4)	0.052 (3)
C2	0.1451 (4)	0.3358 (11)	0.1722 (5)	0.064 (4)
C3	0.1588 (4)	0.2048 (12)	0.1482 (5)	0.068 (4)
C4	0.1568 (4)	0.0941 (10)	0.1981 (6)	0.064 (4)
C5	0.1392 (4)	0.1149 (8)	0.2729 (5)	0.046 (3)
C6	0.1247 (3)	0.2486 (8)	0.2987 (4)	0.038 (3)
C7	0.1093 (3)	0.2716 (8)	0.3827 (4)	0.044 (3)
C8	0.0259 (4)	0.2785 (9)	0.4862 (4)	0.071 (4)
C9	−0.0034 (4)	0.1286 (9)	0.3735 (4)	0.064 (3)
C10	−0.0109 (4)	0.3846 (10)	0.3621 (5)	0.075 (4)
N2	0.3338 (3)	0.7234 (7)	0.1633 (3)	0.051 (3)
C11	0.3348 (5)	0.4088 (12)	0.0717 (5)	0.085 (4)
C12	0.3569 (7)	0.2688 (12)	0.0722 (6)	0.100 (5)
C13	0.4312 (8)	0.2410 (13)	0.0857 (7)	0.109 (6)
C14	0.4779 (6)	0.3488 (14)	0.0932 (6)	0.099 (5)
C15	0.4564 (5)	0.4857 (13)	0.0941 (5)	0.088 (5)
C16	0.3830 (5)	0.5197 (10)	0.0844 (5)	0.064 (4)
C17	0.3582 (5)	0.6713 (10)	0.0848 (4)	0.073 (4)
C18	0.3256 (5)	0.8760 (9)	0.1598 (5)	0.076 (4)
C19	0.3886 (4)	0.6858 (9)	0.2273 (4)	0.062 (3)
C20	0.2636 (4)	0.6583 (11)	0.1809 (5)	0.085 (4)
O1A	0.4911 (6)	0.3954 (17)	0.3595 (9)	0.077 (5)*	0.52 (2)
N3	0.3753 (4)	0.4171 (9)	0.3886 (4)	0.072 (3)
C21	0.3042 (4)	0.3588 (12)	0.3654 (6)	0.095 (5)
C22A	0.3193 (10)	0.265 (2)	0.2951 (10)	0.081 (7)*	0.52 (2)
C23A	0.3950 (9)	0.2057 (17)	0.3247 (13)	0.077 (7)*	0.52 (2)
C24	0.4271 (5)	0.3446 (11)	0.3604 (6)	0.083 (4)
C25	0.3863 (5)	0.5317 (10)	0.4408 (5)	0.087 (4)
C22B	0.3177 (10)	0.220 (2)	0.3232 (15)	0.0810*	0.48 (2)
C23B	0.3951 (10)	0.253 (3)	0.2932 (12)	0.0770*	0.48 (2)
O1B	0.4937 (6)	0.3430 (19)	0.3859 (10)	0.0770*	0.48 (2)
Ni1	0.17935 (5)	0.77257 (10)	0.42154 (5)	0.0453 (3)
Cl1	0.28444 (12)	0.8474 (3)	0.37619 (13)	0.0778 (10)
Cl2	0.09412 (15)	0.7329 (3)	0.32833 (13)	0.0917 (10)
Cl3	0.18332 (12)	0.5816 (2)	0.50048 (12)	0.0670 (8)
Cl4	0.14932 (11)	0.9520 (2)	0.49889 (11)	0.0603 (8)
H1	0.11620	0.45110	0.26560	0.0620*
H2	0.14780	0.41090	0.13800	0.0760*
H3	0.16970	0.18930	0.09710	0.0820*
H4	0.16760	0.00390	0.18130	0.0770*
H5	0.13690	0.03870	0.30640	0.0550*
H7A	0.12830	0.36280	0.39880	0.0520*
H7B	0.13480	0.20060	0.41370	0.0520*
H8A	0.04500	0.36810	0.50290	0.1060*
H8B	0.05380	0.20440	0.51090	0.1060*
H8C	−0.02330	0.27090	0.50010	0.1060*
H9A	−0.04980	0.11790	0.39450	0.0970*
H9B	0.02740	0.05260	0.39100	0.0970*
H9C	−0.00860	0.12730	0.31800	0.0970*
H10A	−0.01290	0.37190	0.30710	0.1130*
H10B	0.01310	0.47160	0.37520	0.1130*
H10C	−0.05900	0.38720	0.37980	0.1130*
H11	0.28620	0.42910	0.06250	0.1020*
H12	0.32390	0.19600	0.06390	0.1200*
H13	0.44780	0.14870	0.08930	0.1310*
H14	0.52700	0.32900	0.09790	0.1190*
H15	0.49050	0.55700	0.10110	0.1050*
H17A	0.31850	0.68210	0.04660	0.0880*
H17B	0.39730	0.73080	0.06930	0.0880*
H18A	0.29490	0.90080	0.11540	0.1140*
H18B	0.37200	0.91900	0.15570	0.1140*
H18C	0.30440	0.90870	0.20580	0.1140*
H19A	0.43330	0.73240	0.21880	0.0930*
H19B	0.39600	0.58570	0.22800	0.0930*
H19C	0.37140	0.71530	0.27600	0.0930*
H20A	0.24670	0.69930	0.22720	0.1270*
H20B	0.27000	0.55870	0.18820	0.1270*
H20C	0.22900	0.67490	0.13870	0.1270*
H21A	0.27030	0.43320	0.35090	0.1140*	0.52 (2)
H21B	0.28510	0.30380	0.40690	0.1140*	0.52 (2)
H23B	0.42270	0.17120	0.28270	0.0930*	0.52 (2)
H25A	0.43660	0.53800	0.45660	0.1310*
H25B	0.35870	0.51670	0.48540	0.1310*
H25C	0.37110	0.61760	0.41570	0.1310*
H22A	0.32210	0.31870	0.24790	0.0970*	0.52 (2)
H22B	0.28380	0.19020	0.28750	0.0970*	0.52 (2)
H23A	0.39090	0.13240	0.36320	0.0930*	0.52 (2)
H21C	0.27750	0.42390	0.33150	0.1140*	0.48 (2)
H21D	0.27660	0.34190	0.41050	0.1140*	0.48 (2)
H22C	0.28230	0.20440	0.28090	0.0970*	0.48 (2)
H22D	0.31850	0.14030	0.35810	0.0970*	0.48 (2)
H23C	0.42280	0.16760	0.28700	0.0930*	0.48 (2)
H23D	0.39200	0.30470	0.24480	0.0930*	0.48 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.035 (4)	0.064 (5)	0.038 (3)	−0.003 (3)	0.002 (3)	−0.001 (3)
C1	0.048 (5)	0.048 (5)	0.058 (6)	0.007 (4)	−0.003 (4)	0.011 (4)
C2	0.053 (6)	0.086 (7)	0.052 (6)	−0.010 (5)	0.005 (4)	0.021 (5)
C3	0.044 (5)	0.113 (9)	0.046 (5)	−0.005 (6)	−0.004 (4)	−0.018 (6)
C4	0.045 (5)	0.076 (7)	0.072 (7)	0.000 (5)	0.002 (5)	−0.035 (6)
C5	0.030 (4)	0.049 (5)	0.059 (5)	−0.005 (4)	0.003 (4)	0.003 (4)
C6	0.029 (4)	0.044 (5)	0.040 (4)	−0.004 (4)	−0.004 (3)	−0.004 (4)
C7	0.032 (4)	0.057 (5)	0.041 (4)	−0.003 (4)	−0.002 (3)	−0.002 (4)
C8	0.060 (6)	0.118 (8)	0.035 (4)	0.000 (6)	0.007 (4)	0.000 (5)
C9	0.052 (6)	0.085 (7)	0.056 (5)	−0.024 (5)	0.001 (4)	−0.010 (5)
C10	0.055 (6)	0.115 (8)	0.056 (6)	0.027 (6)	0.004 (4)	0.003 (6)
N2	0.041 (4)	0.070 (5)	0.041 (4)	0.009 (4)	0.004 (3)	−0.001 (3)
C11	0.072 (7)	0.100 (9)	0.083 (7)	0.001 (7)	0.003 (5)	−0.030 (6)
C12	0.107 (10)	0.077 (9)	0.117 (9)	0.009 (7)	0.007 (7)	−0.034 (7)
C13	0.106 (10)	0.090 (10)	0.133 (11)	0.028 (9)	0.013 (8)	−0.020 (8)
C14	0.077 (8)	0.106 (10)	0.116 (9)	0.035 (8)	0.014 (7)	−0.020 (8)
C15	0.067 (7)	0.116 (10)	0.081 (7)	0.020 (7)	0.008 (5)	−0.014 (7)
C16	0.078 (7)	0.067 (7)	0.046 (5)	0.016 (6)	0.008 (5)	−0.004 (5)
C17	0.074 (6)	0.109 (8)	0.037 (5)	0.000 (6)	0.007 (4)	−0.005 (5)
C18	0.071 (7)	0.077 (7)	0.081 (7)	0.013 (5)	0.001 (5)	0.003 (5)
C19	0.050 (5)	0.094 (7)	0.040 (5)	0.010 (5)	−0.009 (4)	0.004 (4)
C20	0.050 (6)	0.133 (9)	0.072 (6)	−0.013 (6)	0.013 (5)	−0.014 (6)
N3	0.051 (5)	0.083 (6)	0.083 (6)	0.004 (5)	0.011 (4)	0.005 (5)
C21	0.031 (5)	0.153 (11)	0.101 (8)	−0.009 (6)	−0.006 (5)	0.018 (8)
C24	0.055 (7)	0.097 (8)	0.097 (8)	−0.004 (6)	−0.005 (6)	−0.018 (7)
C25	0.084 (7)	0.087 (8)	0.088 (7)	−0.008 (6)	−0.005 (6)	−0.003 (7)
Ni1	0.0529 (6)	0.0509 (6)	0.0323 (5)	0.0027 (6)	0.0050 (4)	−0.0013 (5)
Cl1	0.0646 (15)	0.108 (2)	0.0632 (15)	0.0046 (14)	0.0262 (12)	0.0041 (14)
Cl2	0.125 (2)	0.0733 (17)	0.0711 (15)	−0.0133 (16)	−0.0476 (15)	−0.0014 (14)
Cl3	0.0802 (15)	0.0634 (15)	0.0565 (14)	−0.0027 (13)	−0.0047 (11)	0.0139 (11)
Cl4	0.0679 (14)	0.0665 (15)	0.0475 (12)	0.0098 (12)	0.0111 (10)	−0.0152 (11)

Geometric parameters (Å, º)

Ni1—Cl1	2.258 (3)	C12—C13	1.41 (2)
Ni1—Cl2	2.231 (3)	C13—C14	1.343 (18)
Ni1—Cl3	2.269 (2)	C14—C15	1.360 (18)
Ni1—Cl4	2.256 (2)	C15—C16	1.403 (13)
O1A—C24	1.284 (15)	C16—C17	1.511 (13)
O1B—C24	1.291 (15)	C11—H11	0.9300
N1—C7	1.534 (8)	C12—H12	0.9300
N1—C9	1.498 (10)	C13—H13	0.9300
N1—C8	1.504 (9)	C14—H14	0.9300
N1—C10	1.483 (11)	C15—H15	0.9300
N2—C18	1.458 (11)	C17—H17B	0.9700
N2—C19	1.507 (9)	C17—H17A	0.9700
N2—C17	1.538 (9)	C18—H18B	0.9600
N2—C20	1.490 (10)	C18—H18A	0.9600
N3—C21	1.468 (11)	C18—H18C	0.9600
N3—C24	1.300 (12)	C19—H19C	0.9600
N3—C25	1.422 (12)	C19—H19B	0.9600
C1—C6	1.370 (10)	C19—H19A	0.9600
C1—C2	1.411 (11)	C20—H20A	0.9600
C2—C3	1.340 (15)	C20—H20B	0.9600
C3—C4	1.362 (14)	C20—H20C	0.9600
C4—C5	1.367 (13)	C21—C22B	1.53 (2)
C5—C6	1.377 (11)	C21—C22A	1.55 (2)
C6—C7	1.514 (10)	C22A—C23A	1.58 (3)
C1—H1	0.9300	C22B—C23B	1.59 (3)
C2—H2	0.9300	C23A—C24	1.56 (2)
C3—H3	0.9300	C23B—C24	1.55 (3)
C4—H4	0.9300	C21—H21D	0.9700
C5—H5	0.9300	C21—H21A	0.9700
C7—H7A	0.9700	C21—H21B	0.9700
C7—H7B	0.9700	C21—H21C	0.9700
C8—H8B	0.9600	C22A—H22B	0.9700
C8—H8A	0.9600	C22A—H22A	0.9700
C8—H8C	0.9600	C22B—H22D	0.9700
C9—H9B	0.9600	C22B—H22C	0.9700
C9—H9C	0.9600	C23A—H23B	0.9700
C9—H9A	0.9600	C23A—H23A	0.9700
C10—H10A	0.9600	C23B—H23C	0.9700
C10—H10B	0.9600	C23B—H23D	0.9700
C10—H10C	0.9600	C25—H25B	0.9600
C11—C12	1.391 (16)	C25—H25C	0.9600
C11—C16	1.392 (14)	C25—H25A	0.9600
Ni1···C5^i	4.188 (8)	H7B···H8B	2.3200
Ni1···H5^i	3.2900	H7B···H9B	2.4500
Ni1···H8C^ii	3.2900	H7B···Cl4^x	2.7900
Ni1···H17A^iii	3.3100	H7B···H5	2.4100
Cl1···C19	3.645 (8)	H8A···H10B	2.4600
Cl1···Cl4	3.519 (3)	H8A···H7A	2.4400
Cl2···Cl3	3.628 (3)	H8B···Cl4^x	3.0000
Cl3···Cl2	3.628 (3)	H8B···H9B	2.5500
Cl3···Cl4	3.572 (3)	H8B···H7B	2.3200
Cl4···Cl1	3.519 (3)	H8C···Ni1^ii	3.2900
Cl4···C2^iii	3.619 (9)	H8C···H9A	2.3700
Cl4···Cl3	3.572 (3)	H8C···H10C	2.4200
Cl1···H20A	2.9900	H9A···Cl4^ii	2.7600
Cl1···H17A^iii	3.0000	H9A···H8C	2.3700
Cl1···H19C	2.7400	H9A···H10C	2.5700
Cl1···H25C	2.7700	H9B···H7B	2.4500
Cl1···H18C	3.0500	H9B···H5	2.5700
Cl1···H22D^i	2.8700	H9B···C5	3.0500
Cl2···H10B	3.0300	H9B···Cl4^x	3.0100
Cl2···H9C^iv	3.0800	H9B···H8B	2.5500
Cl2···H5^i	3.0400	H9B···C6	3.1000
Cl2···H10A^iv	3.0200	H9C···H10A	2.3300
Cl2···H1	2.9200	H9C···Cl2^ix	3.0800
Cl3···H7A	2.8700	H9C···C5	2.9000
Cl3···H3^v	3.0900	H9C···C6	2.7700
Cl3···H18A^iii	2.8000	H10A···Cl2^ix	3.0200
Cl4···H7B^i	2.7900	H10A···H9C	2.3300
Cl4···H9B^i	3.0100	H10A···C1	2.8300
Cl4···H9A^ii	2.7600	H10A···C6	2.8200
Cl4···H8B^i	3.0000	H10B···H7A	2.3900
Cl4···H2^iii	2.7400	H10B···Cl2	3.0300
Cl4···H11^iii	2.9400	H10B···H8A	2.4600
Cl4···H20C^iii	3.0200	H10C···H4^iv	2.4900
O1A···C19^vi	3.403 (16)	H10C···C4^iv	2.9500
O1B···C19^vi	3.364 (17)	H10C···H9A	2.5700
O1B···C17^vi	3.215 (16)	H10C···H8C	2.4200
O1A···H17B^vi	2.8300	H11···H17A	2.4900
O1A···H13^vii	2.7800	H11···C20	3.0300
O1A···H19A^vi	2.5300	H11···Cl4^viii	2.9400
O1A···H25A	2.4200	H11···H20B	2.5300
O1A···H18B^vi	2.5800	H12···H25B^xi	2.5400
O1B···H18B^vi	2.7300	H13···O1A^vi	2.7800
O1B···H19A^vi	2.5500	H13···H25A^vi	2.5600
O1B···H25A	2.4900	H15···O1B^vii	2.7400
O1B···H15^vi	2.7400	H15···H23A^vii	2.3700
O1B···H17B^vi	2.3800	H15···H17B	2.4300
C1···C10	3.312 (11)	H15···C23A^vii	2.8100
C2···Cl4^viii	3.619 (9)	H17A···Cl1^viii	3.0000
C4···C10^ix	3.476 (12)	H17A···Ni1^viii	3.3100
C5···C22B	3.53 (2)	H17A···H11	2.4900
C5···C9	3.251 (11)	H17A···H18A	2.4500
C5···Ni1^x	4.188 (8)	H17A···H20C	2.3700
C6···C22B	3.60 (2)	H17B···H15	2.4300
C9···C5	3.251 (11)	H17B···H18B	2.3900
C10···C4^iv	3.476 (12)	H17B···O1A^vii	2.8300
C10···C1	3.312 (11)	H17B···O1B^vii	2.3800
C11···C20	3.348 (14)	H18A···H20C	2.5100
C15···C19	3.291 (13)	H18A···H17A	2.4500
C17···O1B^vii	3.215 (16)	H18A···Cl3^viii	2.8000
C19···O1B^vii	3.364 (17)	H18B···O1B^vii	2.7300
C19···O1A^vii	3.403 (16)	H18B···H19A	2.3400
C19···C15	3.291 (13)	H18B···H17B	2.3900
C19···Cl1	3.645 (8)	H18B···O1A^vii	2.5800
C20···C11	3.348 (14)	H18C···H19C	2.5000
C22B···C5	3.53 (2)	H18C···Cl1	3.0500
C22B···C6	3.60 (2)	H18C···H20A	2.3000
C1···H10A	2.8300	H19A···O1B^vii	2.5500
C4···H10C^ix	2.9500	H19A···O1A^vii	2.5300
C4···H22B	2.9000	H19A···H18B	2.3400
C4···H22C	2.8700	H19B···C16	2.5600
C5···H22C	2.7900	H19B···H20B	2.4200
C5···H9C	2.9000	H19B···C15	2.8000
C5···H22B	2.7800	H19C···H25C	2.5900
C5···H9B	3.0500	H19C···Cl1	2.7400
C6···H9B	3.1000	H19C···H20A	2.4300
C6···H22C	2.9900	H19C···H18C	2.5000
C6···H10A	2.8200	H20A···H19C	2.4300
C6···H22B	3.0200	H20A···H18C	2.3000
C6···H9C	2.7700	H20A···Cl1	2.9900
C9···H5	3.0300	H20B···H11	2.5300
C10···H1	3.0300	H20B···C16	2.8600
C11···H20B	2.7900	H20B···C11	2.7900
C12···H23D	3.0400	H20B···H19B	2.4200
C13···H23D	2.9500	H20C···H17A	2.3700
C15···H19B	2.8000	H20C···H18A	2.5100
C16···H19B	2.5600	H20C···Cl4^viii	3.0200
C16···H20B	2.8600	H21D···H25B	2.5600
C20···H11	3.0300	H22B···C5	2.7800
C23A···H15^vi	2.8100	H22B···C6	3.0200
H1···C10	3.0300	H22B···C4	2.9000
H1···Cl2	2.9200	H22C···C6	2.9900
H1···H7A	2.4500	H22C···C4	2.8700
H2···Cl4^viii	2.7400	H22C···C5	2.7900
H3···Cl3^xi	3.0900	H22D···Cl1^x	2.8700
H4···H10C^ix	2.4900	H23A···H15^vi	2.3700
H5···Ni1^x	3.2900	H23D···C13	2.9500
H5···H9B	2.5700	H23D···C12	3.0400
H5···Cl2^x	3.0400	H25A···H13^vii	2.5600
H5···H7B	2.4100	H25A···O1A	2.4200
H5···C9	3.0300	H25A···O1B	2.4900
H7A···H1	2.4500	H25B···H21D	2.5600
H7A···H8A	2.4400	H25B···H12^v	2.5400
H7A···H10B	2.3900	H25C···Cl1	2.7700
H7A···Cl3	2.8700	H25C···H19C	2.5900
Cl1—Ni1—Cl2	113.24 (9)	C14—C13—H13	120.00
Cl1—Ni1—Cl3	117.41 (10)	C13—C14—H14	119.00
Cl1—Ni1—Cl4	102.44 (9)	C15—C14—H14	119.00
Cl2—Ni1—Cl3	107.43 (10)	C14—C15—H15	120.00
Cl2—Ni1—Cl4	111.62 (10)	C16—C15—H15	120.00
Cl3—Ni1—Cl4	104.27 (8)	C16—C17—H17A	109.00
C8—N1—C10	109.4 (6)	C16—C17—H17B	109.00
C7—N1—C8	106.4 (5)	H17A—C17—H17B	108.00
C7—N1—C9	110.6 (6)	N2—C17—H17A	109.00
C7—N1—C10	110.9 (6)	N2—C17—H17B	109.00
C8—N1—C9	109.6 (6)	N2—C18—H18C	110.00
C9—N1—C10	110.0 (6)	N2—C18—H18A	109.00
C17—N2—C19	110.8 (6)	N2—C18—H18B	109.00
C17—N2—C20	110.5 (6)	H18A—C18—H18C	109.00
C18—N2—C19	109.3 (6)	H18B—C18—H18C	110.00
C18—N2—C20	109.3 (6)	H18A—C18—H18B	109.00
C19—N2—C20	108.4 (6)	N2—C19—H19B	110.00
C17—N2—C18	108.6 (6)	N2—C19—H19A	110.00
C24—N3—C25	124.1 (8)	H19A—C19—H19C	109.00
C21—N3—C24	111.8 (8)	H19B—C19—H19C	109.00
C21—N3—C25	124.0 (8)	H19A—C19—H19B	109.00
C2—C1—C6	118.6 (7)	N2—C19—H19C	109.00
C1—C2—C3	120.5 (9)	H20A—C20—H20B	109.00
C2—C3—C4	120.5 (8)	N2—C20—H20A	109.00
C3—C4—C5	120.4 (9)	N2—C20—H20C	109.00
C4—C5—C6	120.1 (8)	H20B—C20—H20C	110.00
C1—C6—C7	120.3 (7)	H20A—C20—H20C	109.00
C5—C6—C7	119.7 (7)	N2—C20—H20B	109.00
C1—C6—C5	120.0 (7)	N3—C21—C22B	106.6 (9)
N1—C7—C6	114.7 (5)	N3—C21—C22A	103.5 (9)
C2—C1—H1	121.00	C21—C22A—C23A	98.4 (13)
C6—C1—H1	121.00	C21—C22B—C23B	99.3 (15)
C3—C2—H2	120.00	C22A—C23A—C24	98.2 (12)
C1—C2—H2	120.00	C22B—C23B—C24	100.5 (15)
C2—C3—H3	120.00	O1B—C24—C23B	125.0 (13)
C4—C3—H3	120.00	O1A—C24—C23A	130.3 (12)
C5—C4—H4	120.00	N3—C24—C23B	108.6 (10)
C3—C4—H4	120.00	O1A—C24—N3	120.7 (11)
C4—C5—H5	120.00	N3—C24—C23A	108.8 (10)
C6—C5—H5	120.00	O1B—C24—N3	126.4 (12)
C6—C7—H7B	109.00	C22A—C21—H21A	111.00
H7A—C7—H7B	108.00	N3—C21—H21A	111.00
C6—C7—H7A	109.00	N3—C21—H21B	111.00
N1—C7—H7B	109.00	N3—C21—H21C	110.00
N1—C7—H7A	108.00	N3—C21—H21D	110.00
N1—C8—H8C	109.00	H21C—C21—H21D	108.00
N1—C8—H8A	110.00	H21A—C21—H21B	109.00
N1—C8—H8B	110.00	C22B—C21—H21C	111.00
H8A—C8—H8C	109.00	C22A—C21—H21B	111.00
H8B—C8—H8C	109.00	C22B—C21—H21D	110.00
H8A—C8—H8B	109.00	C23A—C22A—H22A	112.00
N1—C9—H9C	109.00	C23A—C22A—H22B	112.00
N1—C9—H9B	109.00	C21—C22A—H22B	112.00
N1—C9—H9A	109.00	C21—C22A—H22A	112.00
H9A—C9—H9C	110.00	H22A—C22A—H22B	110.00
H9B—C9—H9C	109.00	C21—C22B—H22D	112.00
H9A—C9—H9B	109.00	H22C—C22B—H22D	110.00
H10B—C10—H10C	109.00	C23B—C22B—H22D	112.00
N1—C10—H10A	110.00	C21—C22B—H22C	112.00
N1—C10—H10C	109.00	C23B—C22B—H22C	112.00
H10A—C10—H10C	109.00	C22A—C23A—H23B	112.00
H10A—C10—H10B	110.00	C24—C23A—H23A	112.00
N1—C10—H10B	109.00	C24—C23A—H23B	112.00
C12—C11—C16	122.3 (9)	H23A—C23A—H23B	110.00
C11—C12—C13	117.7 (11)	C22A—C23A—H23A	112.00
C12—C13—C14	119.6 (11)	C24—C23B—H23C	112.00
C13—C14—C15	122.7 (11)	C24—C23B—H23D	112.00
C14—C15—C16	120.2 (10)	C22B—C23B—H23C	112.00
C15—C16—C17	120.9 (9)	H23C—C23B—H23D	110.00
C11—C16—C15	117.3 (9)	C22B—C23B—H23D	112.00
C11—C16—C17	121.8 (8)	N3—C25—H25B	109.00
N2—C17—C16	114.5 (6)	N3—C25—H25C	109.00
C16—C11—H11	119.00	N3—C25—H25A	109.00
C12—C11—H11	119.00	H25A—C25—H25C	109.00
C13—C12—H12	121.00	H25B—C25—H25C	109.00
C11—C12—H12	121.00	H25A—C25—H25B	109.00
C12—C13—H13	120.00
C8—N1—C7—C6	175.3 (6)	C4—C5—C6—C1	1.1 (11)
C9—N1—C7—C6	56.4 (8)	C4—C5—C6—C7	−176.7 (6)
C10—N1—C7—C6	−65.9 (8)	C5—C6—C7—N1	−92.4 (8)
C20—N2—C17—C16	−71.6 (9)	C1—C6—C7—N1	89.9 (8)
C18—N2—C17—C16	168.6 (7)	C12—C11—C16—C17	−179.2 (8)
C19—N2—C17—C16	48.6 (9)	C16—C11—C12—C13	−0.4 (15)
C25—N3—C24—O1A	−20.6 (16)	C12—C11—C16—C15	3.1 (13)
C21—N3—C24—O1A	164.4 (12)	C11—C12—C13—C14	−3.7 (16)
C21—N3—C24—C23A	−10.4 (13)	C12—C13—C14—C15	5.0 (17)
C25—N3—C21—C22A	166.6 (10)	C13—C14—C15—C16	−2.2 (16)
C25—N3—C24—C23A	164.7 (11)	C14—C15—C16—C11	−1.9 (13)
C24—N3—C21—C22A	−18.3 (12)	C14—C15—C16—C17	−179.7 (8)
C2—C1—C6—C5	−1.2 (10)	C15—C16—C17—N2	−96.4 (10)
C6—C1—C2—C3	1.4 (11)	C11—C16—C17—N2	86.0 (10)
C2—C1—C6—C7	176.6 (6)	N3—C21—C22A—C23A	37.5 (13)
C1—C2—C3—C4	−1.5 (12)	C21—C22A—C23A—C24	−41.1 (14)
C2—C3—C4—C5	1.5 (12)	C22A—C23A—C24—O1A	−140.3 (15)
C3—C4—C5—C6	−1.3 (11)	C22A—C23A—C24—N3	33.8 (15)

Symmetry codes: (i) x, y+1, z; (ii) −x, −y+1, −z+1; (iii) x, −y+3/2, z+1/2; (iv) −x, y+1/2, −z+1/2; (v) x, −y+1/2, z+1/2; (vi) −x+1, y−1/2, −z+1/2; (vii) −x+1, y+1/2, −z+1/2; (viii) x, −y+3/2, z−1/2; (ix) −x, y−1/2, −z+1/2; (x) x, y−1, z; (xi) x, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cl4^viii	0.93	2.74	3.619 (9)	158
C7—H7B···Cl4^x	0.97	2.79	3.694 (8)	156
C9—H9A···Cl4^ii	0.96	2.76	3.670 (8)	158
C17—H17B···O1B^vii	0.96	2.38	3.215 (16)	144
C18—H18A···Cl3^viii	0.96	2.80	3.738 (9)	165
C18—H18B···O1A^vii	0.96	2.58	3.445 (15)	150
C19—H19A···O1A^vii	0.96	2.53	3.403 (16)	151
C19—H19A···O1B^vii	0.96	2.55	3.364 (17)	143
C19—H19C···Cl1	0.96	2.74	3.645 (8)	158
C25—H25C···Cl1	0.96	2.77	3.686 (10)	159

Symmetry codes: (ii) −x, −y+1, −z+1; (vii) −x+1, y+1/2, −z+1/2; (viii) x, −y+3/2, z−1/2; (x) x, y−1, z.