Bis{2-[({[3-(dimethylazaniumyl)propyl]imino}methyl)phenyl]sulfanido}nickel(II) tetra­phenyl­borate

Meloccaro, A.; Zimmerman, J.R.; Eichhorn, D.M.

doi:10.1107/S2414314617010677

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 7| July 2017| x171067

https://doi.org/10.1107/S2414314617010677

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Bis{2-[({[3-(dimethylazaniumyl)propyl]imino}methyl)phenyl]sulfanido}nickel(II) tetraphenylborate

Alexandra Meloccaro,^a Joshua R. Zimmerman ^a and David M. Eichhorn ^a ^*

^aDepartment of Chemistry, Wichita State University, 1845 Fairmount, Wichita, KS 67260-0051, USA
^*Correspondence e-mail: david.eichhorn@wichita.edu

Edited by R. J. Butcher, Howard University, USA (Received 25 June 2017; accepted 19 July 2017; online 21 July 2017)

In the title compound, [Ni(C₁₂H₁₈N₂S)₂](C₂₄H₂₀B)₂, the Ni^II atom is coordinated by two ligands via the thiolate S and the imine N atoms. The amine N atoms are protonated and interact with the phenyl rings of the BPh₄ anions.

Keywords: crystal structure; nickel complex.

CCDC reference: 1563052

Structure description

We have previously published the reaction of 2,2′-dithiodibenzaldehyde with NiCl₂ and N,N-dimethylethylenediamine to produce a nickel complex of a tridentate ligand in which the Ni is coordinated by the three potential donor atoms (imine N, amine N, and thiolate S) of the ligand with the square-planar Ni coordination sphere completed by a Cl ligand. When Ni(BPh₄)₂ was used as the nickel source, a related species was isolated in which the fourth coordination site is occupied by a thiolate derived from the tridentate ligand. (Zimmerman, et al., 2011 ) In an analogous reaction using N,N-dimethylpropylenediamine, the title complex was isolated in which the potentially tridentate ligand utilizes only the imine N and thiolate S atoms to bind to Ni (Table 1).

Table 1
Selected geometric parameters (Å, °)

Ni1—S1	2.1665 (8)	Ni1—N1	1.922 (2)

S1—Ni1—S1ⁱ	86.93 (4)	N1—Ni1—S1	91.85 (7)
N1—Ni1—S1ⁱ	165.78 (7)	N1ⁱ—Ni1—S1ⁱ	91.85 (7)
N1ⁱ—Ni1—S1	165.78 (7)	N1ⁱ—Ni1—N1	92.73 (13)
Symmetry code: (i) $[-x+1, y, -z+{\script{3\over 2}}]$ .

Two ligands coordinate to the Ni atom, related to each other by a crystallographic twofold rotation axis (Fig. 1). The coordination around Ni deviates somewhat from ideal square planar, with the chelate rings of the two ligands rotated by 19.40 (9)° with respect to each other. The amine N atoms are protonated, with each proton participating in a hydrogen bond with a phenyl ring of one BPh₄⁻ anion (Fig. 2, Table 2).

Table 2
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C25–C30 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯Cg	0.98	2.54	3.510 (3)	171

Figure 1
The molecular structure of the cation in the title compound, with displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity.

Figure 2
Part of the crystal structure of the title compound showing interactions between the protonated amine groups on the cation and the BPh₄ anions, indicated by red lines connecting the N—H hydrogen atom and the orange sphere representing the centroid of the phenyl ring.

Synthesis and crystallization

The title compound was synthesized and crystallized by layering a solution of 0.10 g (0.90 mmol) of N,N-dimethylpropylenediamine and 0.701 g (1.0 mmol) of [Ni(BPh₄)₂] in 20 mL of ethyl acetate on top of a solution of 0.123 g (0.45 mmol) of 2,2′-dithiodibenzaldehyde in 10 mL of dichloromethane.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3.

Table 3
Experimental details

Crystal data
Chemical formula	[Ni(C₁₂H₁₈N₂S)₂](C₂₄H₂₀B)₂
M_r	1141.81
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	150
a, b, c (Å)	16.376 (2), 9.9864 (14), 36.605 (5)
β (°)	99.419 (4)
V (Å³)	5905.6 (14)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.45
Crystal size (mm)	0.63 × 0.60 × 0.34

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Numerical (SADABS; Bruker, 2012 )
T_min, T_max	0.599, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	30373, 6401, 4454
R_int	0.076
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.109, 1.05
No. of reflections	6401
No. of parameters	368
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.71
Computer programs: APEX2 (Bruker, 2013 ), SAINT (Bruker, 2013), SHELXT (Sheldrick, 2015 ), XL (Sheldrick, 2008 ), OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 1563052

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314617010677/bv4008sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617010677/bv4008Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015); program(s) used to refine structure: XL (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Bis{2-[({[3-(dimethylazaniumyl)propyl]imino}methyl)phenyl]sulfanido}nickel(II) tetraphenylborate top

Crystal data top

[Ni(C₁₂H₁₈N₂S₂)₂](C₂₄H₂₀B)₂	F(000) = 2424
M_r = 1141.81	D_x = 1.284 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.376 (2) Å	Cell parameters from 4652 reflections
b = 9.9864 (14) Å	θ = 2.6–24.3°
c = 36.605 (5) Å	µ = 0.45 mm⁻¹
β = 99.419 (4)°	T = 150 K
V = 5905.6 (14) Å³	Block, violet
Z = 4	0.63 × 0.60 × 0.34 mm

Data collection top

Bruker APEXII CCD diffractometer	6401 independent reflections
Radiation source: sealed X-ray tube	4454 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.076
Detector resolution: 5.6 pixels mm^-1	θ_max = 27.1°, θ_min = 3.1°
φ and ω scans	h = −20→20
Absorption correction: numerical (SADABS; Bruker, 2012)	k = −12→12
T_min = 0.599, T_max = 0.746	l = −46→46
30373 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.054	H-atom parameters constrained
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.029P)² + 11.6381P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
6401 reflections	Δρ_max = 0.30 e Å⁻³
368 parameters	Δρ_min = −0.71 e Å⁻³
0 restraints

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.

Refinement. 1. Fixed Uiso

At 1.2 times of:

All C(H) groups, All C(H,H) groups, All N(H) groups

At 1.5 times of:

All C(H,H,H) groups

2.a Ternary CH refined with riding coordinates:

N2(H2)

2.b Secondary CH2 refined with riding coordinates:

C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)

2.c Aromatic/amide H refined with riding coordinates:

C18(H18), C3(H3), C17(H17), C15(H15), C1(H1), C16(H16), C14(H14), C6(H6),

C32(H32), C5(H5), C4(H4), C33(H33), C34(H34), C36(H36), C35(H35), C24(H24),

C26(H26), C23(H23), C20(H20), C21(H21), C30(H30), C22(H22), C29(H29), C27(H27),

C28(H28)

2.d Idealised Me refined as rotating group:

C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ni1	0.5000	0.94419 (5)	0.7500	0.01869 (13)
S1	0.40969 (4)	1.10165 (7)	0.75171 (2)	0.02515 (18)
N1	0.41471 (13)	0.8114 (2)	0.73848 (6)	0.0198 (5)
N2	0.40986 (14)	0.9765 (2)	0.62926 (6)	0.0281 (6)
H2	0.4357	0.9225	0.6120	0.034*
C18	0.50475 (16)	0.4326 (3)	0.66288 (7)	0.0220 (6)
H18	0.4515	0.4090	0.6518	0.026*
C3	0.26569 (17)	0.8453 (3)	0.80122 (8)	0.0271 (7)
H3	0.2463	0.7577	0.7984	0.033*
C2	0.32047 (16)	0.8932 (3)	0.77834 (7)	0.0211 (6)
C17	0.52741 (18)	0.4125 (3)	0.70094 (8)	0.0275 (7)
H17	0.4896	0.3758	0.7145	0.033*
C15	0.66161 (19)	0.4988 (3)	0.69757 (8)	0.0285 (7)
H15	0.7149	0.5210	0.7089	0.034*
C13	0.55877 (17)	0.4869 (2)	0.64052 (7)	0.0209 (6)
C1	0.34617 (17)	0.8015 (3)	0.75121 (7)	0.0218 (6)
H1	0.3107	0.7315	0.7426	0.026*
C31	0.45004 (16)	0.4282 (3)	0.57731 (7)	0.0208 (6)
C16	0.60599 (19)	0.4470 (3)	0.71857 (8)	0.0281 (6)
H16	0.6211	0.4356	0.7440	0.034*
C14	0.63840 (17)	0.5177 (3)	0.65982 (8)	0.0253 (6)
H14	0.6773	0.5526	0.6465	0.030*
C6	0.31900 (17)	1.1093 (3)	0.80796 (8)	0.0274 (7)
H6	0.3353	1.1985	0.8102	0.033*
C19	0.61271 (16)	0.4398 (3)	0.57707 (7)	0.0209 (6)
C32	0.37278 (16)	0.4651 (3)	0.58659 (8)	0.0247 (6)
H32	0.3711	0.5340	0.6035	0.030*
C5	0.26801 (18)	1.0579 (3)	0.83128 (8)	0.0318 (7)
H5	0.2522	1.1123	0.8495	0.038*
C25	0.52708 (16)	0.6677 (3)	0.58324 (8)	0.0215 (6)
C8	0.42913 (17)	0.7166 (3)	0.70892 (7)	0.0226 (6)
H8A	0.3794	0.6643	0.7011	0.027*
H8B	0.4734	0.6555	0.7186	0.027*
C7	0.34641 (16)	1.0285 (3)	0.78095 (7)	0.0223 (6)
C4	0.24024 (17)	0.9263 (3)	0.82782 (8)	0.0303 (7)
H4	0.2050	0.8932	0.8432	0.036*
C33	0.29891 (18)	0.4027 (3)	0.57146 (8)	0.0303 (7)
H33	0.2496	0.4292	0.5788	0.036*
C34	0.29856 (18)	0.3015 (3)	0.54565 (8)	0.0297 (7)
H34	0.2494	0.2591	0.5356	0.036*
C36	0.44618 (18)	0.3265 (3)	0.55081 (7)	0.0241 (6)
H36	0.4952	0.2989	0.5434	0.029*
C35	0.37274 (18)	0.2643 (3)	0.53491 (8)	0.0292 (7)
H35	0.3735	0.1980	0.5171	0.035*
C24	0.64779 (17)	0.3167 (3)	0.59048 (8)	0.0253 (6)
H24	0.6304	0.2786	0.6111	0.030*
C26	0.57679 (17)	0.7696 (3)	0.60160 (8)	0.0261 (6)
H26	0.6133	0.7481	0.6230	0.031*
C23	0.70681 (19)	0.2500 (3)	0.57433 (8)	0.0337 (7)
H23	0.7279	0.1686	0.5840	0.040*
C20	0.64204 (17)	0.4912 (3)	0.54601 (7)	0.0252 (6)
H20	0.6209	0.5721	0.5361	0.030*
C9	0.45220 (17)	0.7912 (3)	0.67557 (7)	0.0253 (6)
H9A	0.5018	0.8436	0.6835	0.030*
H9B	0.4645	0.7266	0.6574	0.030*
C21	0.70175 (18)	0.4253 (3)	0.52945 (8)	0.0337 (7)
H21	0.7194	0.4624	0.5088	0.040*
C30	0.47271 (19)	0.7095 (3)	0.55167 (8)	0.0328 (7)
H30	0.4379	0.6462	0.5385	0.039*
C22	0.7346 (2)	0.3050 (3)	0.54369 (8)	0.0371 (8)
H22	0.7749	0.2614	0.5329	0.045*
C10	0.38377 (18)	0.8832 (3)	0.65759 (8)	0.0294 (7)
H10A	0.3378	0.8291	0.6457	0.035*
H10B	0.3644	0.9360	0.6767	0.035*
C29	0.4683 (2)	0.8411 (3)	0.53907 (10)	0.0410 (8)
H29	0.4311	0.8639	0.5180	0.049*
C27	0.57369 (19)	0.9017 (3)	0.58911 (9)	0.0346 (8)
H27	0.6086	0.9654	0.6019	0.042*
C28	0.5191 (2)	0.9386 (3)	0.55781 (9)	0.0386 (8)
H28	0.5165	1.0267	0.5495	0.046*
C11	0.4715 (2)	1.0792 (3)	0.64582 (9)	0.0417 (8)
H11A	0.4503	1.1264	0.6651	0.063*
H11B	0.4813	1.1413	0.6270	0.063*
H11C	0.5225	1.0357	0.6560	0.063*
C12	0.3369 (2)	1.0444 (4)	0.60779 (10)	0.0535 (10)
H12A	0.2976	0.9785	0.5970	0.080*
H12B	0.3542	1.0973	0.5885	0.080*
H12C	0.3119	1.1014	0.6239	0.080*
B1	0.53614 (19)	0.5067 (3)	0.59512 (9)	0.0214 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0205 (3)	0.0140 (2)	0.0217 (3)	0.000	0.0037 (2)	0.000
S1	0.0272 (4)	0.0168 (3)	0.0323 (4)	0.0024 (3)	0.0072 (3)	0.0020 (3)
N1	0.0215 (12)	0.0168 (11)	0.0205 (12)	0.0004 (9)	0.0020 (10)	0.0006 (9)
N2	0.0271 (14)	0.0309 (14)	0.0257 (14)	−0.0052 (11)	0.0028 (11)	0.0043 (11)
C18	0.0215 (14)	0.0193 (13)	0.0264 (15)	−0.0002 (11)	0.0080 (12)	0.0000 (12)
C3	0.0209 (15)	0.0306 (15)	0.0304 (17)	0.0036 (12)	0.0057 (13)	0.0045 (13)
C2	0.0198 (14)	0.0234 (13)	0.0197 (15)	0.0043 (11)	0.0019 (12)	0.0027 (11)
C17	0.0355 (17)	0.0231 (15)	0.0268 (16)	0.0032 (12)	0.0140 (14)	0.0013 (12)
C15	0.0333 (17)	0.0238 (14)	0.0265 (16)	−0.0030 (13)	−0.0005 (13)	−0.0022 (13)
C13	0.0249 (15)	0.0148 (13)	0.0235 (15)	0.0011 (11)	0.0058 (12)	−0.0006 (11)
C1	0.0216 (15)	0.0202 (13)	0.0227 (15)	−0.0010 (11)	0.0009 (12)	0.0008 (12)
C31	0.0238 (14)	0.0189 (13)	0.0195 (14)	0.0005 (11)	0.0033 (11)	0.0046 (11)
C16	0.0443 (18)	0.0236 (14)	0.0162 (14)	0.0084 (14)	0.0040 (13)	0.0005 (12)
C14	0.0261 (16)	0.0234 (15)	0.0269 (16)	−0.0033 (12)	0.0055 (13)	0.0032 (12)
C6	0.0253 (16)	0.0261 (15)	0.0294 (17)	0.0058 (12)	0.0007 (13)	−0.0009 (13)
C19	0.0200 (14)	0.0239 (14)	0.0182 (14)	−0.0049 (12)	0.0014 (11)	−0.0020 (12)
C32	0.0271 (16)	0.0226 (15)	0.0243 (15)	0.0015 (12)	0.0044 (12)	−0.0014 (12)
C5	0.0281 (16)	0.0417 (18)	0.0258 (16)	0.0114 (15)	0.0051 (13)	−0.0018 (14)
C25	0.0188 (14)	0.0219 (14)	0.0247 (15)	0.0015 (11)	0.0066 (12)	0.0012 (12)
C8	0.0278 (16)	0.0179 (13)	0.0210 (15)	−0.0010 (11)	0.0011 (12)	−0.0029 (11)
C7	0.0204 (14)	0.0223 (14)	0.0228 (15)	0.0040 (11)	−0.0001 (12)	0.0020 (11)
C4	0.0257 (16)	0.0400 (18)	0.0275 (16)	0.0073 (13)	0.0107 (13)	0.0057 (14)
C33	0.0210 (15)	0.0350 (16)	0.0346 (18)	0.0023 (13)	0.0036 (13)	0.0070 (14)
C34	0.0267 (16)	0.0303 (16)	0.0290 (17)	−0.0076 (13)	−0.0047 (13)	0.0062 (13)
C36	0.0264 (15)	0.0236 (14)	0.0228 (15)	0.0014 (12)	0.0056 (12)	0.0024 (12)
C35	0.0368 (18)	0.0244 (15)	0.0246 (16)	−0.0023 (13)	−0.0005 (14)	−0.0016 (12)
C24	0.0279 (16)	0.0264 (15)	0.0227 (15)	0.0027 (12)	0.0072 (13)	0.0028 (12)
C26	0.0264 (16)	0.0244 (15)	0.0274 (16)	−0.0002 (12)	0.0045 (13)	−0.0011 (12)
C23	0.0368 (19)	0.0320 (17)	0.0325 (18)	0.0129 (14)	0.0062 (15)	0.0018 (14)
C20	0.0232 (15)	0.0291 (15)	0.0226 (15)	0.0021 (12)	0.0018 (12)	0.0022 (12)
C9	0.0274 (16)	0.0258 (15)	0.0231 (16)	−0.0010 (12)	0.0050 (13)	−0.0060 (12)
C21	0.0340 (17)	0.0462 (19)	0.0227 (16)	−0.0015 (15)	0.0093 (13)	0.0014 (14)
C30	0.0345 (18)	0.0277 (16)	0.0337 (18)	−0.0060 (14)	−0.0011 (14)	0.0044 (14)
C22	0.0356 (18)	0.050 (2)	0.0288 (18)	0.0124 (16)	0.0132 (15)	−0.0058 (15)
C10	0.0286 (17)	0.0350 (16)	0.0246 (16)	−0.0058 (13)	0.0045 (13)	0.0067 (13)
C29	0.038 (2)	0.0376 (18)	0.045 (2)	0.0018 (15)	−0.0015 (16)	0.0166 (16)
C27	0.0342 (18)	0.0243 (15)	0.047 (2)	−0.0066 (13)	0.0123 (16)	−0.0037 (14)
C28	0.0411 (19)	0.0229 (15)	0.054 (2)	0.0015 (15)	0.0138 (17)	0.0105 (15)
C11	0.047 (2)	0.0361 (18)	0.042 (2)	−0.0135 (16)	0.0049 (16)	0.0022 (15)
C12	0.043 (2)	0.063 (2)	0.051 (2)	−0.0031 (19)	−0.0010 (17)	0.029 (2)
B1	0.0221 (17)	0.0225 (15)	0.0198 (17)	−0.0004 (13)	0.0043 (13)	0.0031 (13)

Geometric parameters (Å, º) top

Ni1—S1	2.1665 (8)	C25—C30	1.402 (4)
Ni1—S1ⁱ	2.1665 (8)	C25—B1	1.665 (4)
Ni1—N1ⁱ	1.922 (2)	C8—H8A	0.9700
Ni1—N1	1.922 (2)	C8—H8B	0.9700
S1—C7	1.765 (3)	C8—C9	1.529 (4)
N1—C1	1.287 (3)	C4—H4	0.9300
N1—C8	1.485 (3)	C33—H33	0.9300
N2—H2	0.9800	C33—C34	1.383 (4)
N2—C10	1.507 (3)	C34—H34	0.9300
N2—C11	1.496 (4)	C34—C35	1.387 (4)
N2—C12	1.482 (4)	C36—H36	0.9300
C18—H18	0.9300	C36—C35	1.393 (4)
C18—C17	1.396 (4)	C35—H35	0.9300
C18—C13	1.409 (4)	C24—H24	0.9300
C3—H3	0.9300	C24—C23	1.383 (4)
C3—C2	1.408 (4)	C26—H26	0.9300
C3—C4	1.381 (4)	C26—C27	1.394 (4)
C2—C1	1.463 (4)	C23—H23	0.9300
C2—C7	1.414 (4)	C23—C22	1.391 (4)
C17—H17	0.9300	C20—H20	0.9300
C17—C16	1.385 (4)	C20—C21	1.396 (4)
C15—H15	0.9300	C9—H9A	0.9700
C15—C16	1.385 (4)	C9—H9B	0.9700
C15—C14	1.385 (4)	C9—C10	1.513 (4)
C13—C14	1.412 (4)	C21—H21	0.9300
C13—B1	1.654 (4)	C21—C22	1.384 (4)
C1—H1	0.9300	C30—H30	0.9300
C31—C32	1.411 (4)	C30—C29	1.391 (4)
C31—C36	1.399 (4)	C22—H22	0.9300
C31—B1	1.651 (4)	C10—H10A	0.9700
C16—H16	0.9300	C10—H10B	0.9700
C14—H14	0.9300	C29—H29	0.9300
C6—H6	0.9300	C29—C28	1.386 (4)
C6—C5	1.387 (4)	C27—H27	0.9300
C6—C7	1.406 (4)	C27—C28	1.383 (4)
C19—C24	1.411 (4)	C28—H28	0.9300
C19—C20	1.402 (4)	C11—H11A	0.9600
C19—B1	1.651 (4)	C11—H11B	0.9600
C32—H32	0.9300	C11—H11C	0.9600
C32—C33	1.392 (4)	C12—H12A	0.9600
C5—H5	0.9300	C12—H12B	0.9600
C5—C4	1.390 (4)	C12—H12C	0.9600
C25—C26	1.404 (4)

S1—Ni1—S1ⁱ	86.93 (4)	C32—C33—H33	119.8
N1—Ni1—S1ⁱ	165.78 (7)	C34—C33—C32	120.3 (3)
N1ⁱ—Ni1—S1	165.78 (7)	C34—C33—H33	119.8
N1—Ni1—S1	91.85 (7)	C33—C34—H34	120.6
N1ⁱ—Ni1—S1ⁱ	91.85 (7)	C33—C34—C35	118.9 (3)
N1ⁱ—Ni1—N1	92.73 (13)	C35—C34—H34	120.6
C7—S1—Ni1	100.86 (9)	C31—C36—H36	118.3
C1—N1—Ni1	128.23 (19)	C35—C36—C31	123.4 (3)
C1—N1—C8	117.8 (2)	C35—C36—H36	118.3
C8—N1—Ni1	113.76 (16)	C34—C35—C36	119.9 (3)
C10—N2—H2	107.8	C34—C35—H35	120.1
C11—N2—H2	107.8	C36—C35—H35	120.1
C11—N2—C10	113.2 (2)	C19—C24—H24	118.5
C12—N2—H2	107.8	C23—C24—C19	123.0 (3)
C12—N2—C10	110.7 (2)	C23—C24—H24	118.5
C12—N2—C11	109.5 (3)	C25—C26—H26	118.6
C17—C18—H18	118.5	C27—C26—C25	122.8 (3)
C17—C18—C13	123.1 (3)	C27—C26—H26	118.6
C13—C18—H18	118.5	C24—C23—H23	120.0
C2—C3—H3	119.5	C24—C23—C22	119.9 (3)
C4—C3—H3	119.5	C22—C23—H23	120.0
C4—C3—C2	121.0 (3)	C19—C20—H20	118.7
C3—C2—C1	118.2 (2)	C21—C20—C19	122.5 (3)
C3—C2—C7	119.9 (2)	C21—C20—H20	118.7
C7—C2—C1	121.8 (2)	C8—C9—H9A	109.1
C18—C17—H17	119.9	C8—C9—H9B	109.1
C16—C17—C18	120.3 (3)	H9A—C9—H9B	107.9
C16—C17—H17	119.9	C10—C9—C8	112.4 (2)
C16—C15—H15	119.8	C10—C9—H9A	109.1
C16—C15—C14	120.5 (3)	C10—C9—H9B	109.1
C14—C15—H15	119.8	C20—C21—H21	119.9
C18—C13—C14	114.2 (2)	C22—C21—C20	120.2 (3)
C18—C13—B1	124.8 (2)	C22—C21—H21	119.9
C14—C13—B1	120.9 (2)	C25—C30—H30	118.4
N1—C1—C2	124.2 (2)	C29—C30—C25	123.1 (3)
N1—C1—H1	117.9	C29—C30—H30	118.4
C2—C1—H1	117.9	C23—C22—H22	120.4
C32—C31—B1	121.5 (2)	C21—C22—C23	119.2 (3)
C36—C31—C32	114.6 (2)	C21—C22—H22	120.4
C36—C31—B1	123.9 (2)	N2—C10—C9	113.7 (2)
C17—C16—H16	120.7	N2—C10—H10A	108.8
C15—C16—C17	118.6 (3)	N2—C10—H10B	108.8
C15—C16—H16	120.7	C9—C10—H10A	108.8
C15—C14—C13	123.3 (3)	C9—C10—H10B	108.8
C15—C14—H14	118.3	H10A—C10—H10B	107.7
C13—C14—H14	118.3	C30—C29—H29	119.8
C5—C6—H6	119.5	C28—C29—C30	120.3 (3)
C5—C6—C7	120.9 (3)	C28—C29—H29	119.8
C7—C6—H6	119.5	C26—C27—H27	119.7
C24—C19—B1	120.4 (2)	C28—C27—C26	120.5 (3)
C20—C19—C24	115.3 (2)	C28—C27—H27	119.7
C20—C19—B1	124.1 (2)	C29—C28—H28	120.8
C31—C32—H32	118.6	C27—C28—C29	118.5 (3)
C33—C32—C31	122.8 (3)	C27—C28—H28	120.8
C33—C32—H32	118.6	N2—C11—H11A	109.5
C6—C5—H5	119.5	N2—C11—H11B	109.5
C6—C5—C4	121.0 (3)	N2—C11—H11C	109.5
C4—C5—H5	119.5	H11A—C11—H11B	109.5
C26—C25—B1	123.7 (2)	H11A—C11—H11C	109.5
C30—C25—C26	114.8 (2)	H11B—C11—H11C	109.5
C30—C25—B1	121.3 (2)	N2—C12—H12A	109.5
N1—C8—H8A	109.4	N2—C12—H12B	109.5
N1—C8—H8B	109.4	N2—C12—H12C	109.5
N1—C8—C9	111.1 (2)	H12A—C12—H12B	109.5
H8A—C8—H8B	108.0	H12A—C12—H12C	109.5
C9—C8—H8A	109.4	H12B—C12—H12C	109.5
C9—C8—H8B	109.4	C13—B1—C25	112.0 (2)
C2—C7—S1	123.6 (2)	C31—B1—C13	112.1 (2)
C6—C7—S1	118.4 (2)	C31—B1—C25	108.8 (2)
C6—C7—C2	118.0 (2)	C19—B1—C13	107.1 (2)
C3—C4—C5	119.1 (3)	C19—B1—C31	107.8 (2)
C3—C4—H4	120.5	C19—B1—C25	109.1 (2)
C5—C4—H4	120.5

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C25–C30 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···Cg	0.98	2.54	3.510 (3)	171

Acknowledgements

JRZ acknowledges support from the Graduate Assistance in Areas of National Need program of the US Department of Education. DME acknowledges support from the National Center for Research Resources – NIH COBRE Award P20 RR017708.

Funding information

Funding for this research was provided by: Kansas IDeA Network of Biomedical Research Excellence.

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