Synthesis, characterization, and crystal structures of organonickel(II) com­plexes coordinated to novel 1-bromo-2,6-bis­{[(λ⁵-phosphanyl­idene)imino]­meth­yl}benzene NCN-pincer ligands

A novel family of four 1-bromo-2,6-bis­{[(λ⁵-phosphanyl­idene)imino]­meth­yl}benzene ligands has been synthesized and characterized. The phosphinimino­methyl substituents are decorated with either three phenyl groups, two phenyl and one cyclo­hexyl group, one phenyl and two cyclo­hexyl groups, or three cyclo­hexyl groups. Each ligand was metallated using zero-valent nickel through an oxidative addition to form a family of organonickel(II) com­plexes, namely (2,6-bis­{[(triphenyl-λ⁵-phosphanyl­idene)imino]­meth­yl}phenyl-κ³N,C¹,N′)bromido­nickel(II) di­chloro­methane hemisolvate, [NiBr(C₄₄H₃₇N₂P₂)]·0.5CH₂Cl₂, (2,6-bis­{[(cyclo­hexyl­diphenyl-λ⁵-phosphanyl­idene)imino]­meth­yl}phenyl-κ³N,C¹,N′)bromido­nickel(II) diethyl ether hemisolvate, [NiBr(C₄₄H₄₉N₂P₂)]·0.5C₄H₁₀O, (2,6-bis­{[(di­cyclo­hexyl­phenyl-λ⁵-phosphanyl­idene)imino]­meth­yl}phenyl-κ³N,C¹,N′)bromido­nickel(II), [NiBr(C₄₄H₆₁N₂P₂)], and (2,6-bis­{[(tri­cyclo­hexyl-λ⁵-phosphanyl­idene)imino]­meth­yl}phenyl-κ³N,C¹,N′)bromido­nickel(II), [NiBr(C₄₄H₇₃N₂P₂)]. This family of com­plexes represents a useful opportunity to investigate the impact of incrementally changing the steric characteristics of a com­plex on its structure and reactivity.

Computing details

Data collection: CrystalClear (Rigaku, 2009) for x634, x964b77res, x821b; CrysAlis PRO (Rigaku OD, 2018) for x95777res. Cell refinement: CrystalClear (Rigaku, 2009) for x634, x964b77res, x821b; CrysAlis PRO (Rigaku OD, 2018) for x95777res. Data reduction: CrystalClear (Rigaku, 2009) for x634, x964b77res, x821b; CrysAlis PRO (Rigaku OD, 2018) for x95777res. For all structures, program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

(2,6-Bis{[(triphenyl-λ⁵-phosphanylidene)imino]methyl}phenyl-κ³N,C¹,N')bromidonickel(II) dichlorometahne hemisolvate (x634)

Crystal data

[NiBr(C44H37N2P2)]·0.5C2H2Cl2	F(000) = 3432
Mr = 836.78	Dx = 1.440 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 28.319 (13) Å	Cell parameters from 8496 reflections
b = 11.655 (5) Å	θ = 1.7–27.5°
c = 23.593 (10) Å	µ = 1.72 mm^−1
β = 97.421 (5)°	T = 170 K
V = 7722 (6) Å^3	Block, clear reddish orange
Z = 8	0.38 × 0.37 × 0.18 mm

Data collection

Rigaku Mini template diffractometer	8846 independent reflections
Radiation source: Sealed Tube	6363 reflections with I > 2σ(I)
Graphite Monochromator monochromator	Rint = 0.084
Detector resolution: 13.6612 pixels mm^-1	θmax = 27.5°, θmin = 1.9°
profile data from ω–scans	h = −36→36
Absorption correction: multi-scan (REQAB; Rigaku, 1998)	k = −15→15
Tmin = 0.671, Tmax = 1.000	l = −30→30
40203 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.053	w = 1/[σ^2(Fo^2) + (0.0234P)^2 + 15.3313P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.111	(Δ/σ)max = 0.001
S = 1.07	Δρmax = 0.44 e Å^−3
8846 reflections	Δρmin = −0.67 e Å^−3
466 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00011 (2)
Primary atom site location: dual

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1	0.39449 (2)	0.21211 (3)	0.46942 (2)	0.03433 (12)
Ni1	0.37267 (2)	0.34137 (4)	0.53979 (2)	0.02438 (12)
P1	0.39034 (3)	0.10427 (8)	0.60420 (4)	0.0277 (2)
P2	0.35900 (3)	0.46116 (8)	0.41855 (4)	0.0266 (2)
Cl1	0.52275 (6)	0.30161 (14)	0.69921 (6)	0.0762 (4)
N1	0.37866 (11)	0.2396 (3)	0.60553 (12)	0.0280 (7)
N2	0.35883 (11)	0.4671 (2)	0.48671 (13)	0.0279 (7)
C2	0.37170 (12)	0.4201 (3)	0.65168 (15)	0.0269 (8)
C39	0.31586 (13)	0.3649 (3)	0.37891 (15)	0.0286 (8)
C27	0.33972 (13)	0.5986 (3)	0.38672 (15)	0.0286 (8)
C6	0.35703 (12)	0.5639 (3)	0.57666 (16)	0.0274 (8)
C9	0.38329 (14)	0.0360 (3)	0.67193 (17)	0.0335 (9)
C5	0.35466 (13)	0.6492 (3)	0.61784 (16)	0.0318 (9)
H5	0.3489	0.7268	0.6067	0.038*
C28	0.29177 (13)	0.6290 (3)	0.38399 (16)	0.0321 (9)
H28	0.2700	0.5782	0.3985	0.038*
C26	0.46844 (14)	−0.0426 (3)	0.59761 (16)	0.0340 (9)
H26	0.4488	−0.1035	0.6076	0.041*
C21	0.45061 (13)	0.0687 (3)	0.59257 (16)	0.0300 (8)
C33	0.41737 (13)	0.4374 (3)	0.39662 (16)	0.0300 (8)
C7	0.38196 (14)	0.2957 (3)	0.66242 (15)	0.0318 (9)
H7A	0.4142	0.2855	0.6836	0.038*
H7B	0.3585	0.2619	0.6853	0.038*
C22	0.48031 (14)	0.1574 (3)	0.57892 (17)	0.0346 (9)
H22	0.4686	0.2338	0.5759	0.041*
C4	0.36087 (14)	0.6187 (3)	0.67546 (17)	0.0372 (10)
H4	0.3592	0.6764	0.7036	0.045*
C3	0.36947 (14)	0.5055 (3)	0.69268 (16)	0.0349 (9)
H3	0.3738	0.4865	0.7322	0.042*
C16	0.30242 (13)	0.0811 (3)	0.54078 (17)	0.0346 (9)
H16	0.2953	0.1492	0.5601	0.042*
C40	0.30731 (14)	0.3779 (4)	0.31957 (17)	0.0377 (10)
H40	0.3243	0.4346	0.3015	0.045*
C8	0.35281 (14)	0.5819 (3)	0.51332 (15)	0.0288 (8)
H8A	0.3212	0.6145	0.4990	0.035*
H8B	0.3777	0.6355	0.5038	0.035*
C29	0.27583 (14)	0.7328 (3)	0.36016 (17)	0.0371 (9)
H29	0.2432	0.7532	0.3585	0.045*
C38	0.42544 (14)	0.3719 (3)	0.34941 (18)	0.0379 (10)
H38	0.3995	0.3357	0.3267	0.045*
C23	0.52656 (14)	0.1348 (4)	0.56979 (18)	0.0396 (10)
H23	0.5467	0.1956	0.5608	0.048*
C20	0.35759 (15)	−0.0661 (3)	0.52298 (16)	0.0351 (9)
H20	0.3883	−0.1000	0.5302	0.042*
C1	0.36529 (12)	0.4508 (3)	0.59382 (15)	0.0266 (8)
C15	0.34789 (13)	0.0332 (3)	0.55191 (16)	0.0301 (8)
C32	0.37097 (15)	0.6731 (4)	0.36421 (18)	0.0405 (10)
H32	0.4036	0.6529	0.3652	0.049*
C44	0.28981 (13)	0.2834 (3)	0.40458 (17)	0.0349 (9)
H44	0.2948	0.2736	0.4449	0.042*
C25	0.51475 (14)	−0.0646 (4)	0.58806 (17)	0.0394 (10)
H25	0.5268	−0.1407	0.5914	0.047*
C30	0.30742 (16)	0.8069 (4)	0.33869 (18)	0.0449 (11)
H30	0.2966	0.8785	0.3228	0.054*
C34	0.45604 (14)	0.4912 (4)	0.42840 (18)	0.0401 (10)
H34	0.4510	0.5362	0.4606	0.048*
C31	0.35461 (16)	0.7764 (4)	0.3404 (2)	0.0486 (12)
H31	0.3761	0.8269	0.3252	0.058*
C19	0.32329 (15)	−0.1160 (3)	0.48387 (18)	0.0404 (10)
H19	0.3306	−0.1835	0.4642	0.049*
C37	0.47162 (16)	0.3594 (4)	0.3354 (2)	0.0515 (12)
H37	0.4770	0.3137	0.3035	0.062*
C17	0.26754 (15)	0.0306 (4)	0.50195 (18)	0.0403 (10)
H17	0.2366	0.0635	0.4952	0.048*
C42	0.24913 (15)	0.2294 (4)	0.3125 (2)	0.0480 (12)
H42	0.2264	0.1827	0.2901	0.058*
C43	0.25645 (15)	0.2159 (4)	0.3712 (2)	0.0447 (11)
H43	0.2386	0.1604	0.3889	0.054*
C14	0.33876 (17)	−0.0015 (4)	0.68282 (19)	0.0481 (11)
H14	0.3119	0.0076	0.6546	0.058*
C18	0.27794 (15)	−0.0677 (4)	0.47313 (19)	0.0435 (11)
H18	0.2543	−0.1021	0.4462	0.052*
C24	0.54358 (15)	0.0238 (4)	0.57374 (18)	0.0420 (10)
H24	0.5752	0.0080	0.5666	0.050*
C41	0.27446 (16)	0.3095 (4)	0.28659 (19)	0.0501 (12)
H41	0.2695	0.3181	0.2462	0.060*
C10	0.42175 (17)	0.0244 (4)	0.71473 (18)	0.0481 (12)
H10	0.4523	0.0512	0.7084	0.058*
C36	0.50948 (16)	0.4130 (4)	0.3677 (2)	0.0521 (13)
H36	0.5408	0.4037	0.3582	0.063*
C13	0.3333 (2)	−0.0525 (4)	0.7352 (2)	0.0606 (15)
H13	0.3029	−0.0789	0.7421	0.073*
C35	0.50175 (15)	0.4802 (4)	0.4140 (2)	0.0501 (12)
H35	0.5276	0.5186	0.4357	0.060*
C11	0.4157 (2)	−0.0261 (4)	0.7667 (2)	0.0639 (16)
H11	0.4422	−0.0339	0.7955	0.077*
C12	0.3716 (2)	−0.0648 (4)	0.7765 (2)	0.0670 (17)
H12	0.3677	−0.0999	0.8119	0.080*
C45	0.5000	0.3892 (6)	0.7500	0.0600 (19)
H45A	0.5256	0.4389	0.7691	0.072*	0.5
H45B	0.4744	0.4389	0.7309	0.072*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0443 (2)	0.0312 (2)	0.0297 (2)	0.00805 (17)	0.01306 (18)	−0.00124 (16)
Ni1	0.0270 (2)	0.0245 (3)	0.0222 (2)	0.00222 (19)	0.00534 (19)	−0.00171 (18)
P1	0.0299 (5)	0.0265 (5)	0.0272 (5)	0.0033 (4)	0.0062 (4)	0.0004 (4)
P2	0.0262 (5)	0.0304 (5)	0.0236 (5)	−0.0001 (4)	0.0051 (4)	0.0007 (4)
Cl1	0.0841 (10)	0.0946 (12)	0.0562 (8)	0.0063 (8)	0.0330 (8)	−0.0024 (8)
N1	0.0318 (17)	0.0282 (17)	0.0246 (16)	0.0045 (13)	0.0067 (14)	0.0003 (13)
N2	0.0321 (17)	0.0274 (17)	0.0247 (16)	0.0006 (13)	0.0057 (14)	−0.0008 (13)
C2	0.0249 (18)	0.031 (2)	0.0252 (19)	0.0017 (15)	0.0070 (16)	−0.0021 (15)
C39	0.0280 (19)	0.034 (2)	0.0244 (19)	0.0033 (15)	0.0057 (16)	−0.0071 (15)
C27	0.0285 (19)	0.034 (2)	0.0226 (18)	0.0006 (16)	0.0006 (16)	0.0025 (15)
C6	0.0258 (19)	0.027 (2)	0.029 (2)	0.0015 (15)	0.0046 (16)	−0.0072 (15)
C9	0.044 (2)	0.025 (2)	0.032 (2)	0.0047 (17)	0.0104 (19)	−0.0002 (16)
C5	0.036 (2)	0.025 (2)	0.034 (2)	0.0015 (16)	0.0043 (18)	−0.0046 (16)
C28	0.029 (2)	0.038 (2)	0.029 (2)	−0.0005 (16)	0.0015 (17)	0.0012 (16)
C26	0.036 (2)	0.035 (2)	0.031 (2)	0.0046 (17)	0.0019 (18)	0.0019 (17)
C21	0.028 (2)	0.036 (2)	0.026 (2)	0.0037 (16)	0.0050 (16)	−0.0033 (16)
C33	0.0261 (19)	0.036 (2)	0.029 (2)	0.0032 (16)	0.0085 (17)	0.0065 (16)
C7	0.039 (2)	0.032 (2)	0.0237 (19)	0.0054 (17)	0.0047 (17)	−0.0006 (16)
C22	0.038 (2)	0.029 (2)	0.036 (2)	0.0043 (17)	0.0047 (19)	−0.0035 (17)
C4	0.045 (2)	0.034 (2)	0.033 (2)	0.0061 (18)	0.009 (2)	−0.0139 (17)
C3	0.040 (2)	0.039 (2)	0.025 (2)	0.0057 (18)	0.0048 (18)	−0.0060 (17)
C16	0.030 (2)	0.036 (2)	0.039 (2)	−0.0014 (17)	0.0088 (18)	−0.0091 (18)
C40	0.034 (2)	0.051 (3)	0.027 (2)	−0.0009 (19)	0.0040 (18)	−0.0055 (18)
C8	0.037 (2)	0.0210 (19)	0.028 (2)	0.0011 (15)	0.0040 (17)	−0.0028 (15)
C29	0.034 (2)	0.042 (3)	0.033 (2)	0.0060 (18)	−0.0048 (18)	0.0001 (18)
C38	0.033 (2)	0.041 (2)	0.041 (2)	0.0017 (18)	0.0107 (19)	0.0017 (19)
C23	0.033 (2)	0.043 (3)	0.043 (3)	−0.0030 (18)	0.009 (2)	−0.0019 (19)
C20	0.042 (2)	0.028 (2)	0.034 (2)	0.0065 (17)	0.0017 (19)	−0.0004 (16)
C1	0.0242 (18)	0.029 (2)	0.0263 (19)	−0.0004 (15)	0.0017 (16)	−0.0026 (15)
C15	0.033 (2)	0.029 (2)	0.029 (2)	−0.0028 (16)	0.0058 (17)	0.0042 (15)
C32	0.034 (2)	0.044 (3)	0.044 (3)	−0.0036 (18)	0.009 (2)	0.0071 (19)
C44	0.033 (2)	0.038 (2)	0.035 (2)	0.0010 (17)	0.0068 (18)	−0.0087 (18)
C25	0.041 (2)	0.038 (2)	0.040 (2)	0.0159 (19)	0.006 (2)	0.0011 (18)
C30	0.054 (3)	0.035 (2)	0.042 (3)	−0.001 (2)	−0.004 (2)	0.0102 (19)
C34	0.031 (2)	0.052 (3)	0.036 (2)	−0.0006 (19)	0.0015 (19)	0.0066 (19)
C31	0.051 (3)	0.043 (3)	0.052 (3)	−0.004 (2)	0.007 (2)	0.021 (2)
C19	0.053 (3)	0.028 (2)	0.038 (2)	0.0002 (19)	0.000 (2)	−0.0058 (17)
C37	0.050 (3)	0.056 (3)	0.054 (3)	0.011 (2)	0.025 (3)	0.008 (2)
C17	0.033 (2)	0.044 (3)	0.045 (3)	−0.0029 (18)	0.010 (2)	−0.006 (2)
C42	0.033 (2)	0.057 (3)	0.052 (3)	−0.004 (2)	0.000 (2)	−0.032 (2)
C43	0.034 (2)	0.040 (3)	0.061 (3)	−0.0045 (19)	0.011 (2)	−0.014 (2)
C14	0.060 (3)	0.046 (3)	0.041 (3)	−0.010 (2)	0.015 (2)	0.001 (2)
C18	0.040 (2)	0.044 (3)	0.045 (3)	−0.013 (2)	0.004 (2)	−0.009 (2)
C24	0.032 (2)	0.053 (3)	0.041 (2)	0.0092 (19)	0.009 (2)	−0.007 (2)
C41	0.044 (3)	0.071 (4)	0.033 (2)	0.004 (2)	−0.004 (2)	−0.018 (2)
C10	0.060 (3)	0.053 (3)	0.033 (2)	0.015 (2)	0.010 (2)	0.006 (2)
C36	0.032 (2)	0.065 (3)	0.062 (3)	0.009 (2)	0.019 (2)	0.022 (3)
C13	0.094 (4)	0.048 (3)	0.047 (3)	−0.021 (3)	0.034 (3)	0.000 (2)
C35	0.029 (2)	0.067 (3)	0.055 (3)	−0.002 (2)	0.005 (2)	0.013 (2)
C11	0.097 (4)	0.063 (4)	0.032 (3)	0.032 (3)	0.010 (3)	0.008 (2)
C12	0.129 (5)	0.033 (3)	0.045 (3)	0.008 (3)	0.036 (4)	0.008 (2)
C45	0.063 (5)	0.066 (5)	0.055 (4)	0.000	0.021 (4)	0.000

Geometric parameters (Å, º)

Br1—Ni1	2.3818 (9)	C8—H8B	0.9900
Ni1—N1	1.943 (3)	C29—H29	0.9500
Ni1—N2	1.935 (3)	C29—C30	1.386 (6)
Ni1—C1	1.834 (4)	C38—H38	0.9500
P1—N1	1.612 (3)	C38—C37	1.397 (6)
P1—C9	1.819 (4)	C23—H23	0.9500
P1—C21	1.812 (4)	C23—C24	1.380 (6)
P1—C15	1.808 (4)	C20—H20	0.9500
P2—N2	1.610 (3)	C20—C15	1.388 (5)
P2—C39	1.825 (4)	C20—C19	1.379 (5)
P2—C27	1.823 (4)	C32—H32	0.9500
P2—C33	1.816 (4)	C32—C31	1.383 (6)
Cl1—C45	1.758 (4)	C44—H44	0.9500
N1—C7	1.485 (4)	C44—C43	1.392 (5)
N2—C8	1.497 (4)	C25—H25	0.9500
C2—C7	1.494 (5)	C25—C24	1.383 (6)
C2—C3	1.395 (5)	C30—H30	0.9500
C2—C1	1.400 (5)	C30—C31	1.378 (6)
C39—C40	1.398 (5)	C34—H34	0.9500
C39—C44	1.389 (5)	C34—C35	1.386 (6)
C27—C28	1.397 (5)	C31—H31	0.9500
C27—C32	1.393 (5)	C19—H19	0.9500
C6—C5	1.398 (5)	C19—C18	1.395 (6)
C6—C8	1.498 (5)	C37—H37	0.9500
C6—C1	1.390 (5)	C37—C36	1.382 (7)
C9—C14	1.389 (6)	C17—H17	0.9500
C9—C10	1.393 (6)	C17—C18	1.383 (6)
C5—H5	0.9500	C42—H42	0.9500
C5—C4	1.394 (5)	C42—C43	1.382 (6)
C28—H28	0.9500	C42—C41	1.369 (6)
C28—C29	1.385 (5)	C43—H43	0.9500
C26—H26	0.9500	C14—H14	0.9500
C26—C21	1.392 (5)	C14—C13	1.398 (6)
C26—C25	1.383 (5)	C18—H18	0.9500
C21—C22	1.396 (5)	C24—H24	0.9500
C33—C38	1.394 (5)	C41—H41	0.9500
C33—C34	1.394 (5)	C10—H10	0.9500
C7—H7A	0.9900	C10—C11	1.390 (6)
C7—H7B	0.9900	C36—H36	0.9500
C22—H22	0.9500	C36—C35	1.384 (7)
C22—C23	1.380 (5)	C13—H13	0.9500
C4—H4	0.9500	C13—C12	1.368 (8)
C4—C3	1.393 (5)	C35—H35	0.9500
C3—H3	0.9500	C11—H11	0.9500
C16—H16	0.9500	C11—C12	1.376 (8)
C16—C15	1.397 (5)	C12—H12	0.9500
C16—C17	1.388 (5)	C45—Cl1^i	1.758 (4)
C40—H40	0.9500	C45—H45A	0.9900
C40—C41	1.385 (6)	C45—H45B	0.9900
C8—H8A	0.9900
N1—Ni1—Br1	99.58 (9)	C33—C38—H38	120.0
N2—Ni1—Br1	94.42 (9)	C33—C38—C37	120.1 (4)
N2—Ni1—N1	165.67 (12)	C37—C38—H38	120.0
C1—Ni1—Br1	170.89 (11)	C22—C23—H23	120.0
C1—Ni1—N1	82.87 (15)	C24—C23—C22	119.9 (4)
C1—Ni1—N2	83.76 (15)	C24—C23—H23	120.0
N1—P1—C9	111.38 (16)	C15—C20—H20	119.5
N1—P1—C21	115.24 (17)	C19—C20—H20	119.5
N1—P1—C15	109.97 (17)	C19—C20—C15	120.9 (4)
C21—P1—C9	104.21 (18)	C2—C1—Ni1	119.2 (3)
C15—P1—C9	105.08 (18)	C6—C1—Ni1	119.2 (3)
C15—P1—C21	110.37 (18)	C6—C1—C2	121.5 (3)
N2—P2—C39	116.75 (17)	C16—C15—P1	117.4 (3)
N2—P2—C27	109.52 (16)	C20—C15—P1	124.1 (3)
N2—P2—C33	114.30 (17)	C20—C15—C16	118.5 (4)
C27—P2—C39	100.61 (17)	C27—C32—H32	120.0
C33—P2—C39	109.51 (18)	C31—C32—C27	120.1 (4)
C33—P2—C27	104.58 (17)	C31—C32—H32	120.0
P1—N1—Ni1	125.36 (17)	C39—C44—H44	120.0
C7—N1—Ni1	116.2 (2)	C39—C44—C43	120.0 (4)
C7—N1—P1	117.3 (2)	C43—C44—H44	120.0
P2—N2—Ni1	125.97 (17)	C26—C25—H25	119.9
C8—N2—Ni1	115.5 (2)	C24—C25—C26	120.3 (4)
C8—N2—P2	118.2 (2)	C24—C25—H25	119.9
C3—C2—C7	126.9 (3)	C29—C30—H30	120.1
C3—C2—C1	118.8 (3)	C31—C30—C29	119.9 (4)
C1—C2—C7	114.3 (3)	C31—C30—H30	120.1
C40—C39—P2	117.7 (3)	C33—C34—H34	119.3
C44—C39—P2	123.7 (3)	C35—C34—C33	121.4 (4)
C44—C39—C40	118.5 (4)	C35—C34—H34	119.3
C28—C27—P2	118.7 (3)	C32—C31—H31	119.7
C32—C27—P2	122.3 (3)	C30—C31—C32	120.6 (4)
C32—C27—C28	119.1 (4)	C30—C31—H31	119.7
C5—C6—C8	126.1 (3)	C20—C19—H19	119.9
C1—C6—C5	119.6 (3)	C20—C19—C18	120.2 (4)
C1—C6—C8	114.3 (3)	C18—C19—H19	119.9
C14—C9—P1	120.3 (3)	C38—C37—H37	119.8
C14—C9—C10	118.6 (4)	C36—C37—C38	120.4 (4)
C10—C9—P1	121.0 (3)	C36—C37—H37	119.8
C6—C5—H5	120.5	C16—C17—H17	120.1
C4—C5—C6	119.0 (4)	C18—C17—C16	119.8 (4)
C4—C5—H5	120.5	C18—C17—H17	120.1
C27—C28—H28	119.9	C43—C42—H42	119.8
C29—C28—C27	120.3 (4)	C41—C42—H42	119.8
C29—C28—H28	119.9	C41—C42—C43	120.4 (4)
C21—C26—H26	120.0	C44—C43—H43	119.8
C25—C26—H26	120.0	C42—C43—C44	120.4 (4)
C25—C26—C21	120.0 (4)	C42—C43—H43	119.8
C26—C21—P1	122.6 (3)	C9—C14—H14	119.9
C26—C21—C22	119.2 (4)	C9—C14—C13	120.2 (5)
C22—C21—P1	118.2 (3)	C13—C14—H14	119.9
C38—C33—P2	124.1 (3)	C19—C18—H18	120.2
C34—C33—P2	117.3 (3)	C17—C18—C19	119.6 (4)
C34—C33—C38	118.5 (4)	C17—C18—H18	120.2
N1—C7—C2	106.6 (3)	C23—C24—C25	120.2 (4)
N1—C7—H7A	110.4	C23—C24—H24	119.9
N1—C7—H7B	110.4	C25—C24—H24	119.9
C2—C7—H7A	110.4	C40—C41—H41	120.2
C2—C7—H7B	110.4	C42—C41—C40	119.6 (4)
H7A—C7—H7B	108.6	C42—C41—H41	120.2
C21—C22—H22	119.8	C9—C10—H10	119.8
C23—C22—C21	120.4 (4)	C11—C10—C9	120.4 (5)
C23—C22—H22	119.8	C11—C10—H10	119.8
C5—C4—H4	119.3	C37—C36—H36	120.0
C3—C4—C5	121.4 (3)	C37—C36—C35	120.0 (4)
C3—C4—H4	119.3	C35—C36—H36	120.0
C2—C3—H3	120.1	C14—C13—H13	119.8
C4—C3—C2	119.7 (4)	C12—C13—C14	120.5 (5)
C4—C3—H3	120.1	C12—C13—H13	119.8
C15—C16—H16	119.5	C34—C35—H35	120.2
C17—C16—H16	119.5	C36—C35—C34	119.6 (4)
C17—C16—C15	121.0 (4)	C36—C35—H35	120.2
C39—C40—H40	119.4	C10—C11—H11	119.8
C41—C40—C39	121.1 (4)	C12—C11—C10	120.4 (5)
C41—C40—H40	119.4	C12—C11—H11	119.8
N2—C8—C6	107.2 (3)	C13—C12—C11	119.8 (5)
N2—C8—H8A	110.3	C13—C12—H12	120.1
N2—C8—H8B	110.3	C11—C12—H12	120.1
C6—C8—H8A	110.3	Cl1^i—C45—Cl1	109.1 (4)
C6—C8—H8B	110.3	Cl1—C45—H45A	109.9
H8A—C8—H8B	108.5	Cl1^i—C45—H45A	109.9
C28—C29—H29	120.0	Cl1—C45—H45B	109.9
C28—C29—C30	120.0 (4)	Cl1^i—C45—H45B	109.9
C30—C29—H29	120.0	H45A—C45—H45B	108.3
Ni1—N1—C7—C2	9.0 (4)	C26—C25—C24—C23	1.1 (6)
Ni1—N2—C8—C6	−3.0 (4)	C21—P1—N1—Ni1	70.9 (3)
P1—N1—C7—C2	177.6 (2)	C21—P1—N1—C7	−96.5 (3)
P1—C9—C14—C13	−179.2 (3)	C21—P1—C9—C14	−150.4 (3)
P1—C9—C10—C11	178.9 (4)	C21—P1—C9—C10	32.3 (4)
P1—C21—C22—C23	179.8 (3)	C21—P1—C15—C16	−157.1 (3)
P2—N2—C8—C6	−176.5 (2)	C21—P1—C15—C20	23.8 (4)
P2—C39—C40—C41	−178.8 (3)	C21—C26—C25—C24	0.3 (6)
P2—C39—C44—C43	177.9 (3)	C21—C22—C23—C24	0.5 (6)
P2—C27—C28—C29	179.9 (3)	C33—P2—N2—Ni1	−67.0 (3)
P2—C27—C32—C31	179.9 (3)	C33—P2—N2—C8	105.8 (3)
P2—C33—C38—C37	179.3 (3)	C33—P2—C39—C40	−63.1 (3)
P2—C33—C34—C35	−178.4 (3)	C33—P2—C39—C44	119.7 (3)
N1—Ni1—C1—C2	6.4 (3)	C33—P2—C27—C28	164.9 (3)
N1—Ni1—C1—C6	−178.4 (3)	C33—P2—C27—C32	−13.9 (4)
N1—P1—C9—C14	84.7 (4)	C33—C38—C37—C36	−0.9 (7)
N1—P1—C9—C10	−92.6 (4)	C33—C34—C35—C36	−1.1 (7)
N1—P1—C21—C26	171.4 (3)	C7—C2—C3—C4	178.0 (4)
N1—P1—C21—C22	−7.6 (4)	C7—C2—C1—Ni1	−2.8 (4)
N1—P1—C15—C16	−28.8 (3)	C7—C2—C1—C6	−177.9 (3)
N1—P1—C15—C20	152.0 (3)	C22—C23—C24—C25	−1.4 (7)
N2—Ni1—C1—C2	−178.8 (3)	C3—C2—C7—N1	178.0 (4)
N2—Ni1—C1—C6	−3.6 (3)	C3—C2—C1—Ni1	175.4 (3)
N2—P2—C39—C40	165.0 (3)	C3—C2—C1—C6	0.3 (5)
N2—P2—C39—C44	−12.1 (4)	C16—C17—C18—C19	0.7 (7)
N2—P2—C27—C28	−72.2 (3)	C40—C39—C44—C43	0.7 (6)
N2—P2—C27—C32	109.0 (3)	C8—C6—C5—C4	−177.9 (4)
N2—P2—C33—C38	144.3 (3)	C8—C6—C1—Ni1	2.8 (4)
N2—P2—C33—C34	−37.5 (4)	C8—C6—C1—C2	177.8 (3)
C39—P2—N2—Ni1	62.6 (3)	C29—C30—C31—C32	−0.9 (7)
C39—P2—N2—C8	−124.6 (3)	C38—C33—C34—C35	−0.2 (6)
C39—P2—C27—C28	51.4 (3)	C38—C37—C36—C35	−0.4 (7)
C39—P2—C27—C32	−127.5 (3)	C20—C19—C18—C17	0.0 (7)
C39—P2—C33—C38	11.2 (4)	C1—C2—C7—N1	−4.0 (4)
C39—P2—C33—C34	−170.7 (3)	C1—C2—C3—C4	0.1 (6)
C39—C40—C41—C42	1.4 (7)	C1—C6—C5—C4	0.2 (6)
C39—C44—C43—C42	0.2 (6)	C1—C6—C8—N2	0.3 (4)
C27—P2—N2—Ni1	176.07 (19)	C15—P1—N1—Ni1	−54.6 (3)
C27—P2—N2—C8	−11.2 (3)	C15—P1—N1—C7	138.0 (3)
C27—P2—C39—C40	46.7 (3)	C15—P1—C9—C14	−34.3 (4)
C27—P2—C39—C44	−130.5 (3)	C15—P1—C9—C10	148.4 (3)
C27—P2—C33—C38	−95.9 (4)	C15—P1—C21—C26	−63.3 (4)
C27—P2—C33—C34	82.2 (3)	C15—P1—C21—C22	117.7 (3)
C27—C28—C29—C30	0.3 (6)	C15—C16—C17—C18	−0.9 (6)
C27—C32—C31—C30	0.0 (7)	C15—C20—C19—C18	−0.6 (6)
C6—C5—C4—C3	0.2 (6)	C32—C27—C28—C29	−1.2 (6)
C9—P1—N1—Ni1	−170.7 (2)	C44—C39—C40—C41	−1.5 (6)
C9—P1—N1—C7	21.9 (3)	C25—C26—C21—P1	179.8 (3)
C9—P1—C21—C26	49.0 (4)	C25—C26—C21—C22	−1.2 (6)
C9—P1—C21—C22	−129.9 (3)	C34—C33—C38—C37	1.2 (6)
C9—P1—C15—C16	91.1 (3)	C19—C20—C15—P1	179.6 (3)
C9—P1—C15—C20	−88.0 (4)	C19—C20—C15—C16	0.4 (6)
C9—C14—C13—C12	0.9 (7)	C37—C36—C35—C34	1.5 (7)
C9—C10—C11—C12	−0.3 (7)	C17—C16—C15—P1	−178.9 (3)
C5—C6—C8—N2	178.5 (3)	C17—C16—C15—C20	0.3 (6)
C5—C6—C1—Ni1	−175.6 (3)	C43—C42—C41—C40	−0.5 (7)
C5—C6—C1—C2	−0.5 (5)	C14—C9—C10—C11	1.5 (6)
C5—C4—C3—C2	−0.4 (6)	C14—C13—C12—C11	0.3 (8)
C28—C27—C32—C31	1.1 (6)	C41—C42—C43—C44	−0.3 (7)
C28—C29—C30—C31	0.8 (7)	C10—C9—C14—C13	−1.8 (6)
C26—C21—C22—C23	0.9 (6)	C10—C11—C12—C13	−0.6 (8)

Symmetry code: (i) −x+1, y, −z+3/2.

(2,6-Bis{[(cyclohexyldiphenyl-λ⁵-phosphanylidene)imino]methyl}phenyl-κ³N,C¹,N')bromidonickel(II) butanol hemisolvate (x95777res)

Crystal data

[NiBr(C44H49N2P2)]·0.5C4H10O	Z = 2
Mr = 843.47	F(000) = 882
Triclinic, P1	Dx = 1.353 Mg m^−3
a = 10.1057 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.8342 (10) Å	Cell parameters from 2165 reflections
c = 15.3868 (11) Å	θ = 2.5–23.0°
α = 74.892 (6)°	µ = 1.55 mm^−1
β = 85.365 (6)°	T = 293 K
γ = 89.151 (6)°	Block, clear dark red
V = 2070.0 (3) Å^3	0.5 × 0.4 × 0.3 mm

Data collection

Bruker APEXII CCD diffractometer	9359 independent reflections
Radiation source: Sealed Tube	6137 reflections with I > 2σ(I)
Graphite Monochromator monochromator	Rint = 0.042
Detector resolution: 13.6612 pixels mm^-1	θmax = 27.5°, θmin = 1.8°
φ and ω scans	h = −12→13
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2018)	k = −17→17
Tmin = 0.987, Tmax = 1.000	l = −15→19
12542 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.131	w = 1/[σ^2(Fo^2) + (0.0356P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
9359 reflections	Δρmax = 0.76 e Å^−3
500 parameters	Δρmin = −0.62 e Å^−3
78 restraints

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1	0.52473 (4)	0.23279 (3)	0.85085 (3)	0.03128 (12)
Ni1	0.70581 (5)	0.34300 (4)	0.77095 (3)	0.02380 (13)
P1	0.79918 (10)	0.30788 (8)	0.97946 (7)	0.0236 (2)
P2	0.55928 (10)	0.26562 (8)	0.62436 (7)	0.0258 (2)
O1	1.0000	0.0000	0.5000	0.165 (4)
N1	0.8002 (3)	0.3640 (2)	0.8732 (2)	0.0258 (7)
N2	0.6667 (3)	0.3362 (3)	0.6497 (2)	0.0291 (8)
C1	0.8020 (4)	0.4539 (3)	0.7078 (3)	0.0253 (9)
C2	0.8734 (4)	0.5075 (3)	0.7533 (2)	0.0245 (9)
C3	0.9469 (4)	0.5909 (3)	0.7056 (3)	0.0344 (10)
H3	0.9957	0.6262	0.7360	0.041*
C4	0.9473 (4)	0.6216 (4)	0.6121 (3)	0.0406 (12)
H4	0.9957	0.6781	0.5800	0.049*
C5	0.8757 (4)	0.5684 (4)	0.5662 (3)	0.0388 (11)
H5	0.8768	0.5890	0.5035	0.047*
C6	0.8025 (4)	0.4842 (3)	0.6143 (3)	0.0306 (10)
C7	0.8631 (4)	0.4653 (3)	0.8537 (3)	0.0307 (10)
H7A	0.9505	0.4601	0.8762	0.037*
H7B	0.8092	0.5084	0.8827	0.037*
C8	0.7246 (5)	0.4187 (4)	0.5746 (3)	0.0438 (12)
H8A	0.6545	0.4567	0.5418	0.053*
H8B	0.7816	0.3916	0.5330	0.053*
C9	0.7462 (4)	0.1778 (3)	1.0095 (3)	0.0262 (9)
H9	0.668 (3)	0.172 (3)	0.995 (2)	0.009 (9)*
C10	0.8311 (4)	0.1162 (3)	0.9564 (3)	0.0341 (10)
H10A	0.8268	0.1455	0.8921	0.041*
H10B	0.9230	0.1176	0.9701	0.041*
C11	0.7816 (5)	0.0079 (4)	0.9808 (3)	0.0479 (13)
H11A	0.6932	0.0062	0.9609	0.057*
H11B	0.8396	−0.0307	0.9494	0.057*
C12	0.7779 (5)	−0.0393 (3)	1.0814 (3)	0.0485 (13)
H12A	0.8675	−0.0437	1.1005	0.058*
H12B	0.7421	−0.1067	1.0948	0.058*
C13	0.6929 (5)	0.0218 (3)	1.1334 (3)	0.0404 (11)
H13A	0.6017	0.0212	1.1182	0.049*
H13B	0.6949	−0.0083	1.1977	0.049*
C14	0.7428 (4)	0.1294 (3)	1.1111 (3)	0.0339 (10)
H14A	0.8312	0.1304	1.1311	0.041*
H14B	0.6849	0.1675	1.1431	0.041*
C15	0.9658 (4)	0.2998 (3)	1.0180 (3)	0.0283 (9)
C16	0.9887 (4)	0.2857 (3)	1.1082 (3)	0.0334 (10)
H16	0.9197	0.2940	1.1493	0.040*
C17	1.1144 (5)	0.2590 (4)	1.1377 (3)	0.0440 (12)
H17	1.1289	0.2487	1.1983	0.053*
C18	1.2158 (5)	0.2483 (4)	1.0770 (4)	0.0453 (12)
H18	1.2989	0.2287	1.0969	0.054*
C19	1.1970 (4)	0.2658 (3)	0.9868 (4)	0.0458 (13)
H19	1.2681	0.2607	0.9459	0.055*
C20	1.0711 (4)	0.2913 (3)	0.9563 (3)	0.0338 (10)
H20	1.0579	0.3025	0.8954	0.041*
C21	0.6971 (4)	0.3725 (3)	1.0484 (2)	0.0239 (9)
C22	0.5603 (4)	0.3537 (3)	1.0596 (3)	0.0310 (10)
H22	0.5255	0.3036	1.0376	0.037*
C23	0.4763 (4)	0.4093 (3)	1.1031 (3)	0.0345 (10)
H23	0.3857	0.3953	1.1115	0.041*
C24	0.5259 (4)	0.4853 (3)	1.1342 (3)	0.0348 (10)
H24	0.4687	0.5229	1.1626	0.042*
C25	0.6602 (5)	0.5053 (3)	1.1231 (3)	0.0363 (11)
H25	0.6938	0.5562	1.1445	0.044*
C26	0.7459 (4)	0.4493 (3)	1.0798 (3)	0.0318 (10)
H26	0.8364	0.4636	1.0719	0.038*
C27	0.5782 (4)	0.1304 (3)	0.6714 (3)	0.0293 (9)
H27	0.5195	0.1120	0.7271	0.035*
C28	0.7189 (4)	0.1015 (4)	0.6982 (3)	0.0375 (11)
H28A	0.7806	0.1167	0.6447	0.045*
H28B	0.7451	0.1401	0.7384	0.045*
C29	0.7242 (6)	−0.0098 (4)	0.7451 (4)	0.0554 (14)
H29A	0.6684	−0.0235	0.8013	0.066*
H29B	0.8145	−0.0277	0.7596	0.066*
C30	0.6778 (6)	−0.0740 (4)	0.6862 (4)	0.0602 (16)
H30A	0.7398	−0.0664	0.6334	0.072*
H30B	0.6771	−0.1438	0.7199	0.072*
C31	0.5405 (5)	−0.0448 (4)	0.6565 (3)	0.0498 (13)
H31A	0.4763	−0.0609	0.7087	0.060*
H31B	0.5173	−0.0829	0.6151	0.060*
C32	0.5349 (5)	0.0667 (3)	0.6103 (3)	0.0351 (10)
H32A	0.4450	0.0843	0.5947	0.042*
H32B	0.5925	0.0813	0.5549	0.042*
C33	0.3899 (4)	0.2971 (3)	0.6528 (3)	0.0292 (9)
C34	0.3627 (5)	0.3952 (4)	0.6556 (3)	0.0419 (12)
H34	0.4319	0.4415	0.6441	0.050*
C35	0.2351 (5)	0.4255 (5)	0.6751 (3)	0.0540 (15)
H35	0.2191	0.4915	0.6765	0.065*
C36	0.1328 (5)	0.3580 (5)	0.6923 (3)	0.0547 (15)
H36	0.0468	0.3781	0.7051	0.066*
C37	0.1568 (5)	0.2607 (5)	0.6908 (3)	0.0531 (14)
H37	0.0869	0.2149	0.7035	0.064*
C38	0.2849 (4)	0.2293 (4)	0.6704 (3)	0.0421 (12)
H38	0.2998	0.1633	0.6686	0.051*
C39	0.5709 (4)	0.2825 (3)	0.5023 (3)	0.0297 (10)
C40	0.6899 (4)	0.2592 (3)	0.4604 (3)	0.0364 (11)
H40	0.7620	0.2381	0.4944	0.044*
C41	0.7016 (5)	0.2673 (4)	0.3683 (3)	0.0428 (12)
H41	0.7812	0.2508	0.3410	0.051*
C42	0.5959 (5)	0.2997 (4)	0.3171 (3)	0.0465 (13)
H42	0.6037	0.3051	0.2554	0.056*
C43	0.4792 (5)	0.3239 (4)	0.3581 (3)	0.0488 (13)
H43	0.4080	0.3463	0.3235	0.059*
C44	0.4651 (5)	0.3156 (3)	0.4504 (3)	0.0351 (10)
H44	0.3852	0.3321	0.4772	0.042*
C90	0.9244 (16)	−0.0508 (14)	0.4458 (10)	0.141 (6)	0.575 (11)
H90A	0.9725	−0.1099	0.4390	0.169*	0.575 (11)
H90B	0.8393	−0.0726	0.4783	0.169*	0.575 (11)
C91	0.9014 (19)	0.0135 (19)	0.3549 (10)	0.160 (9)	0.575 (11)
H91A	0.9852	0.0339	0.3215	0.240*	0.575 (11)
H91B	0.8523	0.0716	0.3609	0.240*	0.575 (11)
H91C	0.8518	−0.0234	0.3234	0.240*	0.575 (11)
C90A	0.947 (2)	0.0640 (15)	0.4257 (12)	0.137 (7)	0.425 (11)
H90C	1.0165	0.0870	0.3777	0.165*	0.425 (11)
H90D	0.9086	0.1220	0.4423	0.165*	0.425 (11)
C91A	0.839 (2)	0.007 (2)	0.3926 (16)	0.148 (10)	0.425 (11)
H91D	0.8385	0.0312	0.3282	0.222*	0.425 (11)
H91E	0.7538	0.0189	0.4204	0.222*	0.425 (11)
H91F	0.8577	−0.0630	0.4086	0.222*	0.425 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0286 (2)	0.0377 (3)	0.0273 (2)	−0.00738 (19)	−0.00101 (17)	−0.00807 (18)
Ni1	0.0251 (3)	0.0243 (3)	0.0222 (3)	−0.0026 (2)	−0.0017 (2)	−0.0063 (2)
P1	0.0242 (5)	0.0253 (6)	0.0216 (5)	−0.0008 (4)	−0.0014 (4)	−0.0067 (4)
P2	0.0264 (6)	0.0281 (6)	0.0234 (5)	−0.0008 (5)	−0.0037 (4)	−0.0069 (4)
O1	0.162 (9)	0.186 (11)	0.164 (9)	−0.059 (8)	−0.033 (7)	−0.069 (8)
N1	0.0326 (19)	0.0206 (19)	0.0234 (17)	−0.0059 (15)	−0.0025 (15)	−0.0038 (14)
N2	0.0331 (19)	0.030 (2)	0.0223 (18)	−0.0065 (16)	−0.0045 (15)	−0.0022 (15)
C1	0.026 (2)	0.023 (2)	0.028 (2)	−0.0019 (17)	−0.0031 (17)	−0.0064 (17)
C2	0.029 (2)	0.022 (2)	0.023 (2)	−0.0007 (17)	−0.0008 (17)	−0.0074 (17)
C3	0.041 (3)	0.030 (3)	0.033 (2)	−0.008 (2)	−0.002 (2)	−0.0093 (19)
C4	0.042 (3)	0.038 (3)	0.035 (3)	−0.016 (2)	0.001 (2)	0.002 (2)
C5	0.044 (3)	0.044 (3)	0.026 (2)	−0.014 (2)	−0.004 (2)	−0.002 (2)
C6	0.031 (2)	0.034 (3)	0.025 (2)	−0.0065 (19)	−0.0031 (18)	−0.0047 (18)
C7	0.037 (2)	0.024 (2)	0.034 (2)	−0.0048 (19)	−0.0062 (19)	−0.0122 (18)
C8	0.051 (3)	0.048 (3)	0.028 (2)	−0.023 (2)	−0.005 (2)	−0.002 (2)
C9	0.024 (2)	0.024 (2)	0.030 (2)	0.0020 (18)	−0.0071 (18)	−0.0061 (17)
C10	0.047 (3)	0.028 (3)	0.028 (2)	0.000 (2)	0.000 (2)	−0.0096 (19)
C11	0.058 (3)	0.034 (3)	0.058 (3)	−0.003 (2)	0.001 (3)	−0.024 (2)
C12	0.066 (4)	0.023 (3)	0.054 (3)	−0.001 (2)	0.002 (3)	−0.007 (2)
C13	0.048 (3)	0.032 (3)	0.036 (3)	−0.009 (2)	0.005 (2)	−0.003 (2)
C14	0.040 (3)	0.031 (3)	0.028 (2)	0.000 (2)	0.0013 (19)	−0.0058 (19)
C15	0.026 (2)	0.026 (2)	0.034 (2)	−0.0015 (18)	−0.0012 (18)	−0.0091 (18)
C16	0.030 (2)	0.036 (3)	0.038 (2)	0.003 (2)	−0.0093 (19)	−0.015 (2)
C17	0.041 (3)	0.041 (3)	0.055 (3)	0.004 (2)	−0.024 (2)	−0.016 (2)
C18	0.032 (3)	0.033 (3)	0.075 (4)	0.001 (2)	−0.019 (3)	−0.017 (3)
C19	0.024 (2)	0.029 (3)	0.083 (4)	−0.002 (2)	0.009 (3)	−0.016 (3)
C20	0.031 (2)	0.027 (3)	0.045 (3)	−0.0073 (19)	0.005 (2)	−0.013 (2)
C21	0.026 (2)	0.029 (2)	0.0167 (19)	−0.0020 (17)	0.0009 (16)	−0.0055 (16)
C22	0.032 (2)	0.031 (3)	0.032 (2)	−0.0019 (19)	−0.0039 (19)	−0.0108 (19)
C23	0.029 (2)	0.043 (3)	0.031 (2)	0.005 (2)	−0.0018 (19)	−0.010 (2)
C24	0.041 (3)	0.030 (3)	0.032 (2)	0.008 (2)	−0.002 (2)	−0.0066 (19)
C25	0.056 (3)	0.025 (3)	0.032 (2)	−0.002 (2)	−0.004 (2)	−0.0128 (19)
C26	0.036 (2)	0.026 (2)	0.034 (2)	−0.0061 (19)	−0.0006 (19)	−0.0085 (19)
C27	0.030 (2)	0.031 (3)	0.030 (2)	0.0007 (19)	−0.0017 (18)	−0.0133 (19)
C28	0.036 (3)	0.042 (3)	0.038 (3)	0.009 (2)	−0.010 (2)	−0.014 (2)
C29	0.065 (4)	0.045 (4)	0.061 (3)	0.022 (3)	−0.027 (3)	−0.018 (3)
C30	0.086 (4)	0.039 (3)	0.062 (4)	0.024 (3)	−0.025 (3)	−0.019 (3)
C31	0.075 (4)	0.033 (3)	0.047 (3)	0.003 (3)	−0.007 (3)	−0.020 (2)
C32	0.042 (3)	0.034 (3)	0.031 (2)	0.000 (2)	−0.007 (2)	−0.010 (2)
C33	0.028 (2)	0.038 (3)	0.021 (2)	−0.0014 (19)	−0.0064 (17)	−0.0054 (18)
C34	0.050 (3)	0.034 (3)	0.045 (3)	0.005 (2)	−0.013 (2)	−0.014 (2)
C35	0.056 (3)	0.066 (4)	0.051 (3)	0.032 (3)	−0.021 (3)	−0.031 (3)
C36	0.042 (3)	0.084 (5)	0.041 (3)	0.032 (3)	−0.011 (2)	−0.020 (3)
C37	0.030 (3)	0.074 (4)	0.054 (3)	−0.002 (3)	0.000 (2)	−0.015 (3)
C38	0.030 (2)	0.044 (3)	0.051 (3)	−0.002 (2)	0.002 (2)	−0.012 (2)
C39	0.034 (2)	0.029 (2)	0.027 (2)	−0.0078 (19)	−0.0058 (18)	−0.0089 (18)
C40	0.038 (3)	0.038 (3)	0.033 (2)	−0.004 (2)	−0.003 (2)	−0.009 (2)
C41	0.048 (3)	0.048 (3)	0.031 (3)	−0.010 (2)	0.006 (2)	−0.008 (2)
C42	0.069 (4)	0.044 (3)	0.026 (2)	−0.008 (3)	−0.006 (2)	−0.006 (2)
C43	0.064 (4)	0.046 (3)	0.038 (3)	−0.005 (3)	−0.022 (3)	−0.006 (2)
C44	0.042 (3)	0.030 (3)	0.032 (2)	0.000 (2)	−0.005 (2)	−0.0039 (19)
C90	0.098 (11)	0.198 (15)	0.151 (11)	−0.035 (10)	0.000 (9)	−0.091 (10)
C91	0.103 (14)	0.223 (19)	0.168 (12)	−0.059 (15)	−0.013 (11)	−0.072 (12)
C90A	0.132 (14)	0.178 (14)	0.135 (13)	−0.014 (11)	−0.009 (10)	−0.098 (10)
C91A	0.135 (18)	0.16 (2)	0.18 (2)	−0.005 (15)	−0.033 (15)	−0.091 (17)

Geometric parameters (Å, º)

Br1—Ni1	2.4344 (7)	C21—C26	1.389 (5)
Ni1—N1	1.990 (3)	C22—H22	0.9300
Ni1—N2	1.964 (3)	C22—C23	1.386 (5)
Ni1—C1	1.833 (4)	C23—H23	0.9300
P1—N1	1.616 (3)	C23—C24	1.378 (6)
P1—C9	1.815 (4)	C24—H24	0.9300
P1—C15	1.823 (4)	C24—C25	1.377 (6)
P1—C21	1.811 (4)	C25—H25	0.9300
P2—N2	1.607 (3)	C25—C26	1.397 (6)
P2—C27	1.834 (4)	C26—H26	0.9300
P2—C33	1.808 (4)	C27—H27	0.9800
P2—C39	1.826 (4)	C27—C28	1.531 (6)
O1—C90	1.482 (12)	C27—C32	1.537 (5)
O1—C90^i	1.482 (12)	C28—H28A	0.9700
O1—C90A	1.392 (16)	C28—H28B	0.9700
O1—C90A^i	1.392 (16)	C28—C29	1.523 (7)
N1—C7	1.495 (5)	C29—H29A	0.9700
N2—C8	1.484 (5)	C29—H29B	0.9700
C1—C2	1.387 (5)	C29—C30	1.526 (6)
C1—C6	1.388 (5)	C30—H30A	0.9700
C2—C3	1.385 (5)	C30—H30B	0.9700
C2—C7	1.498 (5)	C30—C31	1.512 (7)
C3—H3	0.9300	C31—H31A	0.9700
C3—C4	1.390 (6)	C31—H31B	0.9700
C4—H4	0.9300	C31—C32	1.523 (6)
C4—C5	1.390 (6)	C32—H32A	0.9700
C5—H5	0.9300	C32—H32B	0.9700
C5—C6	1.393 (6)	C33—C34	1.392 (6)
C6—C8	1.485 (6)	C33—C38	1.389 (6)
C7—H7A	0.9700	C34—H34	0.9300
C7—H7B	0.9700	C34—C35	1.384 (6)
C8—H8A	0.9700	C35—H35	0.9300
C8—H8B	0.9700	C35—C36	1.366 (7)
C9—H9	0.85 (3)	C36—H36	0.9300
C9—C10	1.537 (5)	C36—C37	1.371 (8)
C9—C14	1.530 (5)	C37—H37	0.9300
C10—H10A	0.9700	C37—C38	1.397 (6)
C10—H10B	0.9700	C38—H38	0.9300
C10—C11	1.527 (6)	C39—C40	1.392 (6)
C11—H11A	0.9700	C39—C44	1.386 (6)
C11—H11B	0.9700	C40—H40	0.9300
C11—C12	1.513 (7)	C40—C41	1.388 (6)
C12—H12A	0.9700	C41—H41	0.9300
C12—H12B	0.9700	C41—C42	1.379 (7)
C12—C13	1.521 (6)	C42—H42	0.9300
C13—H13A	0.9700	C42—C43	1.371 (7)
C13—H13B	0.9700	C43—H43	0.9300
C13—C14	1.521 (6)	C43—C44	1.391 (6)
C14—H14A	0.9700	C44—H44	0.9300
C14—H14B	0.9700	C90—H90A	0.9700
C15—C16	1.387 (5)	C90—H90B	0.9700
C15—C20	1.393 (5)	C90—C91	1.482 (16)
C16—H16	0.9300	C91—H91A	0.9600
C16—C17	1.396 (6)	C91—H91B	0.9600
C17—H17	0.9300	C91—H91C	0.9600
C17—C18	1.363 (6)	C90A—H90C	0.9700
C18—H18	0.9300	C90A—H90D	0.9700
C18—C19	1.372 (7)	C90A—C91A	1.544 (17)
C19—H19	0.9300	C91A—H91D	0.9600
C19—C20	1.400 (6)	C91A—H91E	0.9600
C20—H20	0.9300	C91A—H91F	0.9600
C21—C22	1.399 (5)
N1—Ni1—Br1	101.36 (9)	C26—C21—C22	118.7 (4)
N2—Ni1—Br1	95.61 (10)	C21—C22—H22	119.9
N2—Ni1—N1	162.01 (13)	C23—C22—C21	120.3 (4)
C1—Ni1—Br1	162.67 (13)	C23—C22—H22	119.9
C1—Ni1—N1	82.51 (15)	C22—C23—H23	119.7
C1—Ni1—N2	83.05 (15)	C24—C23—C22	120.6 (4)
N1—P1—C9	114.88 (18)	C24—C23—H23	119.7
N1—P1—C15	111.38 (18)	C23—C24—H24	120.1
N1—P1—C21	111.90 (18)	C25—C24—C23	119.9 (4)
C9—P1—C15	102.7 (2)	C25—C24—H24	120.1
C21—P1—C9	108.06 (18)	C24—C25—H25	120.0
C21—P1—C15	107.30 (18)	C24—C25—C26	120.1 (4)
N2—P2—C27	116.16 (19)	C26—C25—H25	120.0
N2—P2—C33	113.08 (19)	C21—C26—C25	120.5 (4)
N2—P2—C39	109.66 (18)	C21—C26—H26	119.8
C33—P2—C27	107.6 (2)	C25—C26—H26	119.8
C33—P2—C39	104.91 (19)	P2—C27—H27	106.6
C39—P2—C27	104.55 (19)	C28—C27—P2	112.9 (3)
C90^i—O1—C90	180.0	C28—C27—H27	106.6
C90A—O1—C90A^i	180.0	C28—C27—C32	109.6 (3)
P1—N1—Ni1	134.54 (19)	C32—C27—P2	114.0 (3)
C7—N1—Ni1	113.2 (2)	C32—C27—H27	106.6
C7—N1—P1	110.6 (2)	C27—C28—H28A	109.6
P2—N2—Ni1	127.39 (19)	C27—C28—H28B	109.6
C8—N2—Ni1	115.0 (3)	H28A—C28—H28B	108.2
C8—N2—P2	116.5 (3)	C29—C28—C27	110.1 (4)
C2—C1—Ni1	120.1 (3)	C29—C28—H28A	109.6
C2—C1—C6	120.3 (4)	C29—C28—H28B	109.6
C6—C1—Ni1	119.6 (3)	C28—C29—H29A	109.3
C1—C2—C7	113.9 (3)	C28—C29—H29B	109.3
C3—C2—C1	120.2 (4)	C28—C29—C30	111.8 (4)
C3—C2—C7	125.9 (4)	H29A—C29—H29B	107.9
C2—C3—H3	120.2	C30—C29—H29A	109.3
C2—C3—C4	119.6 (4)	C30—C29—H29B	109.3
C4—C3—H3	120.2	C29—C30—H30A	109.3
C3—C4—H4	119.8	C29—C30—H30B	109.3
C3—C4—C5	120.4 (4)	H30A—C30—H30B	107.9
C5—C4—H4	119.8	C31—C30—C29	111.7 (4)
C4—C5—H5	120.1	C31—C30—H30A	109.3
C4—C5—C6	119.7 (4)	C31—C30—H30B	109.3
C6—C5—H5	120.1	C30—C31—H31A	109.5
C1—C6—C5	119.7 (4)	C30—C31—H31B	109.5
C1—C6—C8	114.5 (4)	C30—C31—C32	110.7 (4)
C5—C6—C8	125.8 (4)	H31A—C31—H31B	108.1
N1—C7—C2	107.2 (3)	C32—C31—H31A	109.5
N1—C7—H7A	110.3	C32—C31—H31B	109.5
N1—C7—H7B	110.3	C27—C32—H32A	109.3
C2—C7—H7A	110.3	C27—C32—H32B	109.3
C2—C7—H7B	110.3	C31—C32—C27	111.6 (4)
H7A—C7—H7B	108.5	C31—C32—H32A	109.3
N2—C8—C6	107.8 (3)	C31—C32—H32B	109.3
N2—C8—H8A	110.1	H32A—C32—H32B	108.0
N2—C8—H8B	110.1	C34—C33—P2	118.2 (3)
C6—C8—H8A	110.1	C38—C33—P2	123.6 (4)
C6—C8—H8B	110.1	C38—C33—C34	118.2 (4)
H8A—C8—H8B	108.5	C33—C34—H34	119.2
P1—C9—H9	111 (2)	C35—C34—C33	121.6 (5)
C10—C9—P1	111.6 (3)	C35—C34—H34	119.2
C10—C9—H9	104 (2)	C34—C35—H35	120.2
C14—C9—P1	112.7 (3)	C36—C35—C34	119.7 (5)
C14—C9—H9	106 (2)	C36—C35—H35	120.2
C14—C9—C10	110.9 (4)	C35—C36—H36	120.0
C9—C10—H10A	109.5	C35—C36—C37	120.0 (5)
C9—C10—H10B	109.5	C37—C36—H36	120.0
H10A—C10—H10B	108.1	C36—C37—H37	119.6
C11—C10—C9	110.5 (3)	C36—C37—C38	120.9 (5)
C11—C10—H10A	109.5	C38—C37—H37	119.6
C11—C10—H10B	109.5	C33—C38—C37	119.7 (5)
C10—C11—H11A	109.3	C33—C38—H38	120.2
C10—C11—H11B	109.3	C37—C38—H38	120.2
H11A—C11—H11B	107.9	C40—C39—P2	118.4 (3)
C12—C11—C10	111.7 (4)	C44—C39—P2	122.5 (3)
C12—C11—H11A	109.3	C44—C39—C40	119.1 (4)
C12—C11—H11B	109.3	C39—C40—H40	119.8
C11—C12—H12A	109.5	C41—C40—C39	120.4 (4)
C11—C12—H12B	109.5	C41—C40—H40	119.8
C11—C12—C13	110.9 (4)	C40—C41—H41	119.9
H12A—C12—H12B	108.1	C42—C41—C40	120.3 (5)
C13—C12—H12A	109.5	C42—C41—H41	119.9
C13—C12—H12B	109.5	C41—C42—H42	120.3
C12—C13—H13A	109.4	C43—C42—C41	119.4 (4)
C12—C13—H13B	109.4	C43—C42—H42	120.3
H13A—C13—H13B	108.0	C42—C43—H43	119.4
C14—C13—C12	111.0 (4)	C42—C43—C44	121.2 (5)
C14—C13—H13A	109.4	C44—C43—H43	119.4
C14—C13—H13B	109.4	C39—C44—C43	119.7 (4)
C9—C14—H14A	109.5	C39—C44—H44	120.2
C9—C14—H14B	109.5	C43—C44—H44	120.2
C13—C14—C9	110.8 (3)	O1—C90—H90A	108.9
C13—C14—H14A	109.5	O1—C90—H90B	108.9
C13—C14—H14B	109.5	H90A—C90—H90B	107.7
H14A—C14—H14B	108.1	C91—C90—O1	113.5 (13)
C16—C15—P1	122.5 (3)	C91—C90—H90A	108.9
C16—C15—C20	119.3 (4)	C91—C90—H90B	108.9
C20—C15—P1	117.4 (3)	C90—C91—H91A	109.5
C15—C16—H16	119.7	C90—C91—H91B	109.5
C15—C16—C17	120.6 (4)	C90—C91—H91C	109.5
C17—C16—H16	119.7	H91A—C91—H91B	109.5
C16—C17—H17	120.2	H91A—C91—H91C	109.5
C18—C17—C16	119.5 (4)	H91B—C91—H91C	109.5
C18—C17—H17	120.2	O1—C90A—H90C	109.9
C17—C18—H18	119.5	O1—C90A—H90D	109.9
C17—C18—C19	121.0 (5)	O1—C90A—C91A	109.1 (15)
C19—C18—H18	119.5	H90C—C90A—H90D	108.3
C18—C19—H19	119.9	C91A—C90A—H90C	109.9
C18—C19—C20	120.1 (4)	C91A—C90A—H90D	109.9
C20—C19—H19	119.9	C90A—C91A—H91D	109.5
C15—C20—C19	119.4 (4)	C90A—C91A—H91E	109.5
C15—C20—H20	120.3	C90A—C91A—H91F	109.5
C19—C20—H20	120.3	H91D—C91A—H91E	109.5
C22—C21—P1	118.2 (3)	H91D—C91A—H91F	109.5
C26—C21—P1	122.5 (3)	H91E—C91A—H91F	109.5

Symmetry code: (i) −x+2, −y, −z+1.

(2,6-Bis{[(dicyclohexylphenyl-λ⁵-phosphanylidene)imino]methyl}phenyl-κ³N,C¹,N')bromidonickel(II) (x964b77res)

Crystal data

[NiBr(C44H61N2P2)]	F(000) = 1728
Mr = 818.50	Dx = 1.349 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 21.9686 (12) Å	Cell parameters from 6324 reflections
b = 10.4728 (5) Å	θ = 2.2–25.4°
c = 17.5599 (9) Å	µ = 1.59 mm^−1
β = 93.740 (5)°	T = 293 K
V = 4031.5 (4) Å^3	Plate, clear dark red
Z = 4	0.48 × 0.4 × 0.12 mm

Data collection

Rigaku XtaLAB mini diffractometer	9264 independent reflections
Radiation source: Sealed Tube	6380 reflections with I > 2σ(I)
Graphite Monochromator monochromator	Rint = 0.081
Detector resolution: 13.6612 pixels mm^-1	θmax = 27.5°, θmin = 1.9°
profile data from ω–scans	h = −28→28
Absorption correction: multi-scan (REQAB; Rigaku, 1998)	k = −13→13
Tmin = 0.866, Tmax = 1.000	l = −22→22
41828 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.162	w = 1/[σ^2(Fo^2) + (0.0692P)^2 + 6.6008P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
9264 reflections	Δρmax = 1.11 e Å^−3
455 parameters	Δρmin = −1.13 e Å^−3
52 restraints

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.

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

	x	y	z	Uiso*/Ueq
Br1	0.18281 (2)	0.70376 (4)	0.75036 (3)	0.03600 (14)
Ni1	0.26610 (2)	0.58744 (5)	0.69840 (3)	0.02076 (13)
P1	0.15297 (4)	0.40100 (9)	0.63478 (5)	0.0193 (2)
P2	0.34939 (5)	0.73313 (10)	0.83036 (6)	0.0221 (2)
N1	0.22422 (14)	0.4349 (3)	0.65208 (18)	0.0213 (7)
N2	0.32978 (16)	0.7038 (3)	0.74223 (18)	0.0252 (7)
C1	0.32847 (18)	0.5357 (4)	0.6412 (2)	0.0235 (8)
C2	0.32298 (18)	0.4245 (4)	0.5983 (2)	0.0231 (8)
C3	0.36983 (19)	0.3891 (4)	0.5527 (2)	0.0311 (10)
H3	0.3666	0.3144	0.5240	0.037*
C4	0.4212 (2)	0.4657 (5)	0.5501 (3)	0.0357 (10)
H4	0.4525	0.4412	0.5200	0.043*
C5	0.4264 (2)	0.5780 (5)	0.5916 (2)	0.0330 (10)
H5	0.4607	0.6296	0.5887	0.040*
C6	0.37988 (18)	0.6133 (4)	0.6380 (2)	0.0255 (9)
C7	0.26592 (18)	0.3517 (4)	0.6088 (2)	0.0261 (9)
H7A	0.2752	0.2738	0.6370	0.031*
H7B	0.2464	0.3290	0.5595	0.031*
C8	0.37808 (19)	0.7283 (4)	0.6886 (2)	0.0281 (9)
H8A	0.4172	0.7405	0.7165	0.034*
H8B	0.3685	0.8042	0.6585	0.034*
C9	0.10555 (18)	0.4340 (4)	0.7142 (2)	0.0240 (8)
C15	0.11633 (17)	0.4766 (4)	0.5496 (2)	0.0215 (8)
H15	0.0765	0.4359	0.5394	0.026*
C16	0.1051 (2)	0.6209 (4)	0.5620 (2)	0.0311 (10)
H16A	0.0803	0.6325	0.6051	0.037*
H16B	0.1438	0.6638	0.5733	0.037*
C17	0.0727 (2)	0.6802 (4)	0.4905 (3)	0.0369 (11)
H17A	0.0324	0.6430	0.4823	0.044*
H17B	0.0679	0.7712	0.4985	0.044*
C18	0.1081 (2)	0.6587 (5)	0.4202 (3)	0.0430 (12)
H18A	0.0850	0.6927	0.3758	0.052*
H18B	0.1466	0.7043	0.4259	0.052*
C19	0.1203 (2)	0.5180 (5)	0.4082 (2)	0.0379 (11)
H19A	0.1454	0.5078	0.3652	0.045*
H19B	0.0819	0.4743	0.3962	0.045*
C20	0.1525 (2)	0.4576 (5)	0.4790 (2)	0.0310 (10)
H20A	0.1926	0.4955	0.4879	0.037*
H20B	0.1578	0.3669	0.4702	0.037*
C21	0.14367 (18)	0.2303 (4)	0.6209 (2)	0.0219 (8)
C22	0.1032 (2)	0.1764 (4)	0.5645 (2)	0.0288 (9)
H22	0.0829	0.2285	0.5283	0.035*
C23	0.0936 (2)	0.0449 (4)	0.5627 (3)	0.0310 (10)
H23	0.0673	0.0093	0.5249	0.037*
C24	0.1230 (2)	−0.0326 (4)	0.6168 (3)	0.0333 (10)
H24	0.1158	−0.1201	0.6159	0.040*
C25	0.1633 (2)	0.0190 (4)	0.6725 (3)	0.0297 (9)
H25	0.1832	−0.0335	0.7088	0.036*
C26	0.17368 (19)	0.1490 (4)	0.6737 (2)	0.0267 (9)
H26	0.2013	0.1830	0.7106	0.032*
C27	0.29744 (18)	0.6597 (4)	0.8946 (2)	0.0229 (8)
H27	0.2560	0.6854	0.8772	0.028*
C28	0.3004 (2)	0.5131 (4)	0.8892 (3)	0.0315 (10)
H28A	0.2895	0.4867	0.8371	0.038*
H28B	0.3418	0.4847	0.9025	0.038*
C29	0.2570 (2)	0.4510 (5)	0.9428 (3)	0.0362 (11)
H29A	0.2153	0.4728	0.9262	0.043*
H29B	0.2611	0.3589	0.9400	0.043*
C30	0.2699 (2)	0.4939 (5)	1.0247 (3)	0.0393 (11)
H30A	0.3105	0.4668	1.0428	0.047*
H30B	0.2408	0.4546	1.0567	0.047*
C31	0.2651 (2)	0.6386 (5)	1.0303 (2)	0.0351 (10)
H31A	0.2749	0.6648	1.0826	0.042*
H31B	0.2236	0.6647	1.0162	0.042*
C32	0.3085 (2)	0.7056 (4)	0.9780 (2)	0.0312 (10)
H32A	0.3504	0.6878	0.9958	0.037*
H32B	0.3023	0.7972	0.9803	0.037*
C33	0.35341 (18)	0.9034 (4)	0.8523 (2)	0.0251 (8)
H33	0.3645	0.9125	0.9070	0.030*
C34	0.2906 (2)	0.9640 (4)	0.8359 (3)	0.0329 (10)
H34A	0.2772	0.9494	0.7829	0.039*
H34B	0.2616	0.9232	0.8673	0.039*
C35	0.2913 (2)	1.1069 (4)	0.8517 (3)	0.0410 (12)
H35A	0.2513	1.1421	0.8376	0.049*
H35B	0.2999	1.1212	0.9059	0.049*
C36	0.3385 (3)	1.1759 (5)	0.8079 (3)	0.0526 (15)
H36A	0.3394	1.2654	0.8221	0.063*
H36B	0.3275	1.1703	0.7536	0.063*
C37	0.4015 (2)	1.1172 (5)	0.8251 (3)	0.0449 (12)
H37A	0.4306	1.1594	0.7943	0.054*
H37B	0.4142	1.1313	0.8783	0.054*
C38	0.4017 (2)	0.9743 (4)	0.8084 (3)	0.0348 (10)
H38A	0.4417	0.9396	0.8228	0.042*
H38B	0.3934	0.9606	0.7541	0.042*
C39	0.42352 (19)	0.6637 (4)	0.8581 (2)	0.0286 (9)
C40	0.4396 (2)	0.5504 (4)	0.8220 (3)	0.0360 (11)
H40	0.4146	0.5176	0.7819	0.043*
C41	0.4930 (2)	0.4870 (5)	0.8460 (3)	0.0475 (13)
H41	0.5035	0.4118	0.8220	0.057*
C42	0.5303 (3)	0.5345 (6)	0.9051 (4)	0.0606 (17)
H42	0.5659	0.4912	0.9209	0.073*
C43	0.5152 (2)	0.6464 (6)	0.9411 (3)	0.0540 (15)
H43	0.5408	0.6788	0.9808	0.065*
C44	0.4622 (2)	0.7098 (5)	0.9179 (3)	0.0384 (11)
H44	0.4521	0.7847	0.9426	0.046*
C10	0.1334 (2)	0.3798 (5)	0.7894 (2)	0.0303 (9)
H10A	0.1364	0.2876	0.7856	0.036*
H10B	0.1743	0.4136	0.7994	0.036*
C11	0.0944 (2)	0.4146 (6)	0.8553 (3)	0.0415 (12)
H11A	0.0936	0.5066	0.8613	0.050*
H11B	0.1122	0.3778	0.9023	0.050*
C12	0.0294 (2)	0.3649 (7)	0.8400 (3)	0.0509 (14)
H12A	0.0049	0.3897	0.8816	0.061*
H12B	0.0299	0.2724	0.8374	0.061*
C13	0.0010 (2)	0.4189 (7)	0.7649 (3)	0.0521 (15)
H13A	−0.0397	0.3841	0.7552	0.063*
H13B	−0.0026	0.5109	0.7692	0.063*
C14	0.03941 (19)	0.3865 (5)	0.6985 (3)	0.0361 (11)
H14A	0.0217	0.4259	0.6523	0.043*
H14B	0.0395	0.2947	0.6908	0.043*
H9	0.104 (2)	0.533 (4)	0.715 (2)	0.029 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0344 (3)	0.0336 (3)	0.0398 (3)	0.00182 (19)	0.00044 (19)	−0.0061 (2)
Ni1	0.0193 (3)	0.0219 (3)	0.0213 (3)	−0.0028 (2)	0.00286 (19)	−0.0026 (2)
P1	0.0177 (5)	0.0211 (5)	0.0192 (5)	−0.0016 (4)	0.0020 (4)	−0.0019 (4)
P2	0.0205 (5)	0.0226 (5)	0.0233 (5)	−0.0022 (4)	0.0018 (4)	−0.0025 (4)
N1	0.0167 (16)	0.0225 (16)	0.0251 (17)	0.0000 (13)	0.0046 (13)	−0.0050 (13)
N2	0.0270 (18)	0.0264 (18)	0.0222 (17)	−0.0082 (14)	0.0025 (14)	−0.0034 (14)
C1	0.0196 (19)	0.031 (2)	0.0199 (19)	−0.0039 (17)	0.0011 (15)	0.0016 (16)
C2	0.0204 (19)	0.028 (2)	0.0213 (19)	0.0013 (16)	0.0016 (15)	0.0004 (16)
C3	0.025 (2)	0.037 (2)	0.032 (2)	0.0020 (19)	0.0042 (17)	−0.0080 (19)
C4	0.026 (2)	0.048 (3)	0.035 (2)	0.003 (2)	0.0111 (19)	−0.001 (2)
C5	0.022 (2)	0.049 (3)	0.028 (2)	−0.007 (2)	0.0038 (17)	0.004 (2)
C6	0.024 (2)	0.030 (2)	0.022 (2)	−0.0019 (17)	0.0029 (16)	0.0026 (17)
C7	0.024 (2)	0.025 (2)	0.029 (2)	0.0012 (17)	0.0053 (16)	−0.0066 (17)
C8	0.023 (2)	0.036 (2)	0.026 (2)	−0.0120 (18)	0.0021 (16)	0.0003 (18)
C9	0.020 (2)	0.032 (2)	0.0206 (19)	−0.0011 (17)	0.0038 (15)	−0.0025 (17)
C15	0.0178 (19)	0.025 (2)	0.0212 (19)	−0.0037 (16)	0.0000 (15)	0.0004 (16)
C16	0.040 (3)	0.023 (2)	0.029 (2)	−0.0014 (19)	−0.0055 (19)	−0.0005 (18)
C17	0.045 (3)	0.028 (2)	0.036 (3)	−0.001 (2)	−0.011 (2)	0.0035 (19)
C18	0.044 (3)	0.049 (3)	0.033 (3)	−0.014 (2)	−0.012 (2)	0.017 (2)
C19	0.033 (2)	0.059 (3)	0.022 (2)	−0.005 (2)	0.0013 (18)	0.007 (2)
C20	0.029 (2)	0.040 (2)	0.025 (2)	−0.0004 (19)	0.0037 (17)	0.0015 (19)
C21	0.022 (2)	0.0234 (19)	0.0210 (19)	−0.0035 (16)	0.0041 (15)	−0.0012 (16)
C22	0.030 (2)	0.033 (2)	0.024 (2)	−0.0046 (19)	0.0024 (17)	−0.0013 (18)
C23	0.032 (2)	0.029 (2)	0.032 (2)	−0.0101 (19)	−0.0014 (18)	−0.0020 (18)
C24	0.042 (3)	0.023 (2)	0.036 (2)	−0.0086 (19)	0.009 (2)	−0.0033 (19)
C25	0.029 (2)	0.027 (2)	0.034 (2)	0.0014 (18)	0.0084 (18)	0.0072 (18)
C26	0.025 (2)	0.030 (2)	0.025 (2)	−0.0024 (17)	0.0024 (16)	−0.0023 (17)
C27	0.021 (2)	0.028 (2)	0.0199 (19)	−0.0004 (16)	0.0034 (15)	−0.0037 (16)
C28	0.034 (2)	0.030 (2)	0.032 (2)	−0.0065 (19)	0.0070 (19)	−0.0010 (19)
C29	0.039 (3)	0.032 (2)	0.039 (3)	−0.007 (2)	0.012 (2)	0.000 (2)
C30	0.037 (3)	0.045 (3)	0.037 (3)	0.004 (2)	0.009 (2)	0.009 (2)
C31	0.035 (3)	0.048 (3)	0.023 (2)	0.002 (2)	0.0064 (18)	0.000 (2)
C32	0.034 (2)	0.035 (2)	0.025 (2)	−0.0002 (19)	0.0038 (18)	−0.0031 (18)
C33	0.023 (2)	0.024 (2)	0.028 (2)	−0.0004 (16)	−0.0012 (16)	0.0012 (17)
C34	0.028 (2)	0.028 (2)	0.042 (3)	0.0038 (19)	−0.0017 (19)	−0.005 (2)
C35	0.043 (3)	0.031 (2)	0.048 (3)	0.008 (2)	−0.007 (2)	−0.007 (2)
C36	0.073 (4)	0.024 (2)	0.058 (3)	0.007 (3)	−0.013 (3)	0.001 (2)
C37	0.051 (3)	0.031 (2)	0.052 (3)	−0.008 (2)	0.001 (2)	0.000 (2)
C38	0.035 (3)	0.031 (2)	0.038 (3)	−0.005 (2)	0.002 (2)	−0.001 (2)
C39	0.023 (2)	0.031 (2)	0.032 (2)	−0.0009 (18)	0.0056 (17)	0.0046 (18)
C40	0.036 (3)	0.036 (2)	0.037 (3)	0.009 (2)	0.011 (2)	0.000 (2)
C41	0.042 (3)	0.046 (3)	0.057 (3)	0.019 (2)	0.017 (3)	0.008 (3)
C42	0.032 (3)	0.064 (4)	0.085 (5)	0.017 (3)	0.003 (3)	0.028 (4)
C43	0.036 (3)	0.056 (3)	0.068 (4)	−0.008 (3)	−0.016 (3)	0.017 (3)
C44	0.028 (2)	0.037 (3)	0.050 (3)	−0.003 (2)	−0.004 (2)	−0.004 (2)
C10	0.027 (2)	0.044 (3)	0.021 (2)	0.0013 (19)	0.0047 (16)	0.0033 (18)
C11	0.035 (2)	0.066 (3)	0.024 (2)	0.001 (2)	0.0078 (18)	−0.001 (2)
C12	0.034 (2)	0.090 (4)	0.030 (2)	−0.005 (3)	0.0140 (19)	0.003 (3)
C13	0.025 (2)	0.100 (5)	0.032 (2)	0.000 (3)	0.0095 (18)	−0.008 (3)
C14	0.021 (2)	0.060 (3)	0.027 (2)	−0.001 (2)	0.0043 (16)	−0.005 (2)

Geometric parameters (Å, º)

Br1—Ni1	2.4253 (7)	C19—C20	1.527 (6)
Ni1—N1	1.991 (3)	C21—C22	1.405 (6)
Ni1—N2	1.973 (3)	C21—C26	1.393 (6)
Ni1—C1	1.833 (4)	C22—C23	1.393 (6)
P1—N1	1.614 (3)	C23—C24	1.379 (6)
P1—C9	1.827 (4)	C24—C25	1.385 (6)
P1—C15	1.831 (4)	C25—C26	1.380 (6)
P1—C21	1.814 (4)	C27—C28	1.540 (6)
P2—N2	1.609 (3)	C27—C32	1.545 (5)
P2—C27	1.827 (4)	C28—C29	1.528 (6)
P2—C33	1.825 (4)	C29—C30	1.516 (7)
P2—C39	1.821 (4)	C30—C31	1.523 (7)
N1—C7	1.506 (5)	C31—C32	1.534 (6)
N2—C8	1.487 (5)	C33—C34	1.529 (6)
C1—C2	1.387 (6)	C33—C38	1.541 (6)
C1—C6	1.395 (6)	C34—C35	1.522 (6)
C2—C3	1.396 (6)	C35—C36	1.514 (8)
C2—C7	1.489 (6)	C36—C37	1.526 (8)
C3—C4	1.387 (6)	C37—C38	1.525 (6)
C4—C5	1.386 (7)	C39—C40	1.401 (6)
C5—C6	1.398 (6)	C39—C44	1.395 (6)
C6—C8	1.498 (6)	C40—C41	1.389 (7)
C9—C10	1.529 (6)	C41—C42	1.372 (8)
C9—C14	1.544 (6)	C42—C43	1.382 (9)
C15—C16	1.549 (6)	C43—C44	1.379 (7)
C15—C20	1.529 (5)	C10—C11	1.527 (6)
C16—C17	1.532 (6)	C11—C12	1.528 (7)
C17—C18	1.518 (7)	C12—C13	1.529 (7)
C18—C19	1.515 (7)	C13—C14	1.522 (6)
N1—Ni1—Br1	102.53 (9)	C20—C15—C16	109.7 (3)
N2—Ni1—Br1	94.37 (10)	C17—C16—C15	110.5 (3)
N2—Ni1—N1	162.16 (14)	C18—C17—C16	111.8 (4)
C1—Ni1—Br1	164.55 (13)	C19—C18—C17	111.2 (4)
C1—Ni1—N1	83.17 (15)	C18—C19—C20	111.5 (4)
C1—Ni1—N2	81.94 (16)	C19—C20—C15	111.6 (4)
N1—P1—C9	114.13 (18)	C22—C21—P1	123.4 (3)
N1—P1—C15	115.32 (18)	C26—C21—P1	118.0 (3)
N1—P1—C21	109.95 (18)	C26—C21—C22	118.3 (4)
C9—P1—C15	107.41 (18)	C23—C22—C21	120.1 (4)
C21—P1—C9	102.96 (19)	C24—C23—C22	120.2 (4)
C21—P1—C15	106.07 (18)	C23—C24—C25	120.4 (4)
N2—P2—C27	112.03 (18)	C26—C25—C24	119.6 (4)
N2—P2—C33	113.35 (19)	C25—C26—C21	121.5 (4)
N2—P2—C39	111.06 (19)	C28—C27—P2	110.5 (3)
C33—P2—C27	107.71 (18)	C28—C27—C32	111.4 (3)
C39—P2—C27	104.52 (19)	C32—C27—P2	112.9 (3)
C39—P2—C33	107.69 (19)	C29—C28—C27	110.8 (4)
P1—N1—Ni1	132.07 (19)	C30—C29—C28	111.9 (4)
C7—N1—Ni1	113.0 (2)	C29—C30—C31	110.3 (4)
C7—N1—P1	113.1 (3)	C30—C31—C32	111.6 (4)
P2—N2—Ni1	129.2 (2)	C31—C32—C27	111.0 (4)
C8—N2—Ni1	112.1 (2)	C34—C33—P2	109.6 (3)
C8—N2—P2	114.8 (3)	C34—C33—C38	110.3 (4)
C2—C1—Ni1	120.2 (3)	C38—C33—P2	113.0 (3)
C2—C1—C6	120.6 (4)	C35—C34—C33	112.1 (4)
C6—C1—Ni1	119.1 (3)	C36—C35—C34	112.1 (4)
C1—C2—C3	119.6 (4)	C35—C36—C37	110.5 (4)
C1—C2—C7	114.1 (3)	C38—C37—C36	111.8 (4)
C3—C2—C7	126.4 (4)	C37—C38—C33	111.5 (4)
C4—C3—C2	119.8 (4)	C40—C39—P2	117.8 (3)
C5—C4—C3	120.9 (4)	C44—C39—P2	123.6 (3)
C4—C5—C6	119.5 (4)	C44—C39—C40	118.3 (4)
C1—C6—C5	119.6 (4)	C41—C40—C39	120.0 (5)
C1—C6—C8	113.1 (4)	C42—C41—C40	120.5 (5)
C5—C6—C8	127.3 (4)	C41—C42—C43	120.3 (5)
C2—C7—N1	108.1 (3)	C44—C43—C42	119.8 (5)
N2—C8—C6	106.5 (3)	C43—C44—C39	121.1 (5)
C10—C9—P1	111.9 (3)	C11—C10—C9	110.6 (4)
C10—C9—C14	110.7 (4)	C10—C11—C12	110.5 (4)
C14—C9—P1	112.3 (3)	C11—C12—C13	110.4 (4)
C16—C15—P1	111.9 (3)	C14—C13—C12	111.3 (4)
C20—C15—P1	112.5 (3)	C13—C14—C9	110.7 (4)

(2,6-Bis{[(tricyclohexyl-λ⁵-phosphanylidene)imino]methyl}phenyl-κ³N,C¹,N')bromidonickel(II) (x821b)

Crystal data

[NiBr(C44H73N2P2)]	F(000) = 1776
Mr = 830.60	Dx = 1.313 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.569 (9) Å	Cell parameters from 8356 reflections
b = 11.612 (6) Å	θ = 1.8–27.5°
c = 20.608 (10) Å	µ = 1.52 mm^−1
β = 91.521 (5)°	T = 173 K
V = 4203 (4) Å^3	Block, clear reddish violet
Z = 4	0.26 × 0.16 × 0.16 mm

Data collection

Rigaku XtaLAB mini diffractometer	9621 independent reflections
Radiation source: Sealed Tube	6279 reflections with I > 2σ(I)
Graphite Monochromator monochromator	Rint = 0.106
Detector resolution: 13.6612 pixels mm^-1	θmax = 27.6°, θmin = 2.0°
profile data from ω–scans	h = −22→22
Absorption correction: multi-scan (REQAB; Rigaku, 1998)	k = −15→15
Tmin = 0.819, Tmax = 1.000	l = −26→26
43868 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
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) = 0.144	w = 1/[σ^2(Fo^2) + (0.0335P)^2 + 6.2065P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
9621 reflections	Δρmax = 0.63 e Å^−3
455 parameters	Δρmin = −0.88 e Å^−3
288 restraints

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.

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

	x	y	z	Uiso*/Ueq
Br1	0.33814 (3)	0.46623 (4)	0.26395 (2)	0.03458 (14)
Ni1	0.31582 (3)	0.58031 (5)	0.35902 (3)	0.02082 (14)
P1	0.34857 (6)	0.33399 (10)	0.43774 (5)	0.0202 (2)
P2	0.19230 (7)	0.72712 (11)	0.28271 (5)	0.0245 (3)
N1	0.3361 (2)	0.4727 (3)	0.43424 (16)	0.0214 (8)
N2	0.2804 (2)	0.7166 (3)	0.30610 (17)	0.0225 (8)
C1	0.3218 (2)	0.6894 (4)	0.4231 (2)	0.0204 (9)
C2	0.3252 (2)	0.6570 (4)	0.4877 (2)	0.0207 (9)
C3	0.3317 (2)	0.7394 (4)	0.5361 (2)	0.0244 (10)
H3	0.3319	0.7178	0.5795	0.029*
C4	0.3381 (3)	0.8554 (4)	0.5189 (2)	0.0308 (11)
H4	0.3440	0.9108	0.5512	0.037*
C5	0.3357 (3)	0.8890 (4)	0.4540 (2)	0.0296 (11)
H5	0.3400	0.9662	0.4428	0.036*
C6	0.3266 (2)	0.8049 (4)	0.4062 (2)	0.0234 (9)
C7	0.3207 (3)	0.5297 (4)	0.4981 (2)	0.0255 (10)
H7A	0.2706	0.5086	0.5127	0.031*
H7B	0.3582	0.5058	0.5308	0.031*
C8	0.3183 (3)	0.8227 (4)	0.3341 (2)	0.0258 (10)
H8A	0.3679	0.8336	0.3154	0.031*
H8B	0.2875	0.8903	0.3248	0.031*
C21	0.2601 (2)	0.2518 (4)	0.4221 (2)	0.0265 (10)
H21	0.2723	0.1699	0.4276	0.032*
C22	0.1999 (3)	0.2827 (4)	0.4718 (2)	0.0339 (11)
H22A	0.2205	0.2686	0.5152	0.041*
H22B	0.1880	0.3641	0.4683	0.041*
C23	0.1269 (3)	0.2131 (6)	0.4616 (2)	0.0490 (15)
H23A	0.0896	0.2380	0.4926	0.059*
H23B	0.1376	0.1323	0.4695	0.059*
C24	0.0942 (3)	0.2282 (6)	0.3927 (3)	0.0532 (16)
H24A	0.0498	0.1792	0.3866	0.064*
H24B	0.0782	0.3074	0.3864	0.064*
C25	0.1532 (3)	0.1972 (5)	0.3432 (2)	0.0470 (15)
H25A	0.1322	0.2111	0.2999	0.056*
H25B	0.1651	0.1159	0.3468	0.056*
C26	0.2261 (3)	0.2676 (4)	0.3532 (2)	0.0343 (12)
H26A	0.2150	0.3484	0.3458	0.041*
H26B	0.2631	0.2437	0.3218	0.041*
C15	0.3801 (2)	0.2897 (3)	0.52024 (19)	0.0204 (9)
H15	0.3452	0.3278	0.5497	0.025*
C16	0.3750 (3)	0.1607 (4)	0.5360 (2)	0.0268 (10)
H16A	0.3250	0.1316	0.5236	0.032*
H16B	0.4126	0.1185	0.5119	0.032*
C17	0.3895 (3)	0.1435 (4)	0.6089 (2)	0.0321 (11)
H17A	0.3498	0.1819	0.6325	0.039*
H17B	0.3872	0.0619	0.6189	0.039*
C18	0.4668 (3)	0.1909 (4)	0.6311 (2)	0.0344 (12)
H18A	0.4728	0.1822	0.6778	0.041*
H18B	0.5069	0.1470	0.6111	0.041*
C19	0.4748 (3)	0.3174 (4)	0.6133 (2)	0.0308 (11)
H19A	0.5255	0.3441	0.6254	0.037*
H19B	0.4384	0.3627	0.6370	0.037*
C20	0.4608 (2)	0.3339 (4)	0.5403 (2)	0.0264 (10)
H20A	0.4989	0.2919	0.5166	0.032*
H20B	0.4652	0.4149	0.5294	0.032*
C9	0.4152 (3)	0.2892 (4)	0.3774 (2)	0.0227 (9)
C10	0.4885 (2)	0.3596 (4)	0.3786 (2)	0.0264 (10)
H10A	0.4764	0.4409	0.3807	0.032*
H10B	0.5191	0.3399	0.4169	0.032*
C11	0.5338 (3)	0.3355 (4)	0.3178 (2)	0.0319 (11)
H11A	0.5059	0.3653	0.2802	0.038*
H11B	0.5820	0.3759	0.3212	0.038*
C12	0.5487 (3)	0.2084 (4)	0.3081 (2)	0.0358 (12)
H12A	0.5836	0.1812	0.3420	0.043*
H12B	0.5727	0.1970	0.2667	0.043*
C13	0.4754 (3)	0.1383 (4)	0.3095 (2)	0.0374 (12)
H13A	0.4876	0.0571	0.3063	0.045*
H13B	0.4433	0.1586	0.2722	0.045*
C14	0.4319 (3)	0.1598 (4)	0.3715 (2)	0.0312 (11)
H14A	0.4620	0.1340	0.4089	0.037*
H14B	0.3845	0.1168	0.3702	0.037*
C27	0.1218 (3)	0.7277 (4)	0.3482 (2)	0.0284 (10)
H27	0.0709	0.7307	0.3277	0.034*
C28	0.1310 (3)	0.8335 (4)	0.3923 (2)	0.0343 (11)
H28A	0.1835	0.8384	0.4078	0.041*
H28B	0.1197	0.9023	0.3671	0.041*
C29	0.0793 (3)	0.8297 (4)	0.4501 (2)	0.0390 (13)
H29A	0.0266	0.8341	0.4350	0.047*
H29B	0.0896	0.8959	0.4777	0.047*
C30	0.0913 (3)	0.7200 (4)	0.4894 (2)	0.0385 (13)
H30A	0.0572	0.7193	0.5257	0.046*
H30B	0.1432	0.7170	0.5065	0.046*
C31	0.0755 (3)	0.6157 (5)	0.4461 (2)	0.0380 (12)
H31A	0.0228	0.6171	0.4309	0.046*
H31B	0.0836	0.5458	0.4711	0.046*
C32	0.1278 (3)	0.6154 (4)	0.3879 (2)	0.0322 (11)
H32A	0.1146	0.5508	0.3599	0.039*
H32B	0.1801	0.6050	0.4032	0.039*
C33	0.1678 (2)	0.6035 (4)	0.23117 (19)	0.0265 (10)
H33	0.1895	0.5363	0.2536	0.032*
C34	0.2062 (3)	0.6074 (4)	0.1647 (2)	0.0302 (11)
H34A	0.1847	0.6698	0.1389	0.036*
H34B	0.2603	0.6218	0.1710	0.036*
C35	0.1941 (3)	0.4934 (5)	0.1290 (2)	0.0398 (13)
H35A	0.2203	0.4326	0.1529	0.048*
H35B	0.2162	0.4985	0.0865	0.048*
C36	0.1099 (3)	0.4628 (5)	0.1212 (2)	0.0492 (15)
H36A	0.0848	0.5185	0.0929	0.059*
H36B	0.1049	0.3875	0.1011	0.059*
C37	0.0712 (3)	0.4615 (5)	0.1862 (2)	0.0445 (14)
H37A	0.0926	0.4001	0.2130	0.053*
H37B	0.0173	0.4465	0.1795	0.053*
C38	0.0820 (2)	0.5770 (5)	0.2215 (2)	0.0364 (12)
H38A	0.0581	0.5738	0.2633	0.044*
H38B	0.0578	0.6379	0.1962	0.044*
C39	0.1763 (2)	0.8640 (4)	0.2390 (2)	0.0292 (11)
H39	0.1774	0.9237	0.2727	0.035*
C40	0.2391 (3)	0.8975 (4)	0.1924 (2)	0.0346 (12)
H40A	0.2884	0.8902	0.2143	0.042*
H40B	0.2380	0.8455	0.1555	0.042*
C41	0.2281 (3)	1.0211 (4)	0.1686 (2)	0.0424 (13)
H41A	0.2327	1.0735	0.2052	0.051*
H41B	0.2677	1.0402	0.1385	0.051*
C42	0.1507 (3)	1.0363 (5)	0.1354 (3)	0.0528 (16)
H42A	0.1484	0.9907	0.0960	0.063*
H42B	0.1437	1.1165	0.1234	0.063*
C43	0.0871 (3)	0.9994 (5)	0.1795 (3)	0.0481 (15)
H43A	0.0387	1.0050	0.1558	0.058*
H43B	0.0854	1.0515	0.2162	0.058*
C44	0.0976 (3)	0.8760 (4)	0.2043 (2)	0.0374 (12)
H44A	0.0940	0.8226	0.1682	0.045*
H44B	0.0578	0.8575	0.2343	0.045*
H9	0.394 (3)	0.309 (4)	0.344 (2)	0.034 (15)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0464 (3)	0.0340 (3)	0.0233 (2)	0.0065 (2)	0.0020 (2)	−0.0004 (2)
Ni1	0.0236 (3)	0.0216 (3)	0.0172 (3)	0.0009 (2)	0.0005 (2)	−0.0004 (2)
P1	0.0219 (5)	0.0211 (6)	0.0176 (5)	−0.0014 (5)	0.0014 (4)	0.0001 (4)
P2	0.0223 (6)	0.0336 (7)	0.0177 (6)	0.0032 (5)	0.0019 (5)	0.0005 (5)
N1	0.030 (2)	0.0188 (18)	0.0153 (17)	0.0044 (16)	0.0009 (15)	−0.0030 (14)
N2	0.0214 (18)	0.026 (2)	0.0203 (18)	0.0042 (16)	−0.0029 (15)	0.0021 (15)
C1	0.016 (2)	0.021 (2)	0.024 (2)	0.0014 (17)	−0.0015 (17)	0.0004 (17)
C2	0.017 (2)	0.021 (2)	0.024 (2)	0.0037 (17)	0.0012 (17)	−0.0021 (18)
C3	0.024 (2)	0.033 (3)	0.017 (2)	−0.001 (2)	0.0012 (17)	−0.0012 (18)
C4	0.038 (3)	0.030 (3)	0.024 (2)	0.000 (2)	0.002 (2)	−0.006 (2)
C5	0.037 (3)	0.019 (2)	0.032 (3)	−0.004 (2)	−0.003 (2)	−0.0040 (19)
C6	0.024 (2)	0.023 (2)	0.023 (2)	−0.0024 (19)	0.0003 (18)	−0.0009 (18)
C7	0.032 (2)	0.025 (2)	0.021 (2)	0.002 (2)	0.0047 (19)	−0.0020 (18)
C8	0.028 (2)	0.026 (2)	0.023 (2)	−0.001 (2)	−0.0049 (19)	0.0052 (19)
C21	0.027 (2)	0.026 (2)	0.026 (2)	−0.003 (2)	−0.0029 (19)	0.0007 (19)
C22	0.028 (3)	0.045 (3)	0.029 (3)	−0.003 (2)	0.003 (2)	−0.003 (2)
C23	0.030 (3)	0.079 (4)	0.038 (3)	−0.018 (3)	0.002 (2)	0.004 (3)
C24	0.032 (3)	0.077 (5)	0.050 (4)	−0.016 (3)	−0.008 (3)	0.004 (3)
C25	0.043 (3)	0.064 (4)	0.034 (3)	−0.022 (3)	−0.010 (2)	0.001 (3)
C26	0.032 (3)	0.044 (3)	0.027 (3)	−0.007 (2)	−0.004 (2)	0.002 (2)
C15	0.024 (2)	0.018 (2)	0.019 (2)	−0.0013 (18)	0.0007 (17)	0.0031 (17)
C16	0.033 (3)	0.023 (2)	0.024 (2)	−0.005 (2)	−0.0019 (19)	0.0009 (19)
C17	0.043 (3)	0.032 (3)	0.021 (2)	−0.009 (2)	−0.004 (2)	0.005 (2)
C18	0.041 (3)	0.039 (3)	0.022 (2)	0.000 (2)	−0.006 (2)	0.006 (2)
C19	0.032 (3)	0.035 (3)	0.024 (2)	−0.009 (2)	−0.004 (2)	−0.003 (2)
C20	0.025 (2)	0.027 (2)	0.027 (2)	−0.002 (2)	−0.0009 (19)	0.0031 (19)
C9	0.029 (2)	0.019 (2)	0.020 (2)	0.0030 (19)	0.0000 (19)	0.0006 (18)
C10	0.027 (2)	0.028 (2)	0.024 (2)	−0.001 (2)	0.0056 (19)	−0.0028 (19)
C11	0.030 (3)	0.041 (3)	0.025 (2)	0.003 (2)	0.006 (2)	0.000 (2)
C12	0.042 (3)	0.042 (3)	0.024 (2)	0.010 (2)	0.011 (2)	0.000 (2)
C13	0.054 (3)	0.029 (3)	0.030 (3)	0.006 (2)	0.011 (2)	−0.005 (2)
C14	0.043 (3)	0.025 (2)	0.027 (2)	0.004 (2)	0.009 (2)	−0.001 (2)
C27	0.024 (2)	0.041 (3)	0.020 (2)	0.003 (2)	−0.0005 (18)	0.001 (2)
C28	0.043 (3)	0.038 (3)	0.023 (2)	0.006 (2)	0.007 (2)	−0.002 (2)
C29	0.039 (3)	0.050 (3)	0.029 (3)	0.006 (3)	0.011 (2)	−0.003 (2)
C30	0.035 (3)	0.060 (4)	0.021 (2)	0.005 (3)	0.006 (2)	−0.001 (2)
C31	0.031 (3)	0.053 (3)	0.030 (3)	−0.002 (2)	0.006 (2)	0.008 (2)
C32	0.027 (2)	0.043 (3)	0.026 (2)	−0.001 (2)	0.005 (2)	0.001 (2)
C33	0.023 (2)	0.041 (3)	0.015 (2)	0.000 (2)	−0.0035 (17)	−0.0045 (19)
C34	0.024 (2)	0.043 (3)	0.023 (2)	−0.005 (2)	0.0031 (19)	0.000 (2)
C35	0.034 (3)	0.055 (4)	0.030 (3)	−0.008 (3)	0.004 (2)	−0.012 (2)
C36	0.045 (3)	0.073 (4)	0.030 (3)	−0.021 (3)	0.002 (2)	−0.018 (3)
C37	0.039 (3)	0.060 (4)	0.035 (3)	−0.015 (3)	0.003 (2)	−0.007 (3)
C38	0.025 (2)	0.058 (4)	0.026 (3)	−0.003 (2)	0.003 (2)	−0.003 (2)
C39	0.028 (2)	0.037 (3)	0.024 (2)	0.009 (2)	0.0043 (19)	0.001 (2)
C40	0.033 (3)	0.048 (3)	0.023 (2)	0.008 (2)	0.008 (2)	0.005 (2)
C41	0.050 (3)	0.045 (3)	0.034 (3)	0.009 (3)	0.014 (3)	0.010 (2)
C42	0.059 (4)	0.059 (4)	0.041 (3)	0.020 (3)	0.006 (3)	0.018 (3)
C43	0.037 (3)	0.065 (4)	0.042 (3)	0.022 (3)	−0.002 (3)	0.014 (3)
C44	0.032 (3)	0.052 (3)	0.029 (3)	0.011 (2)	0.001 (2)	0.005 (2)

Geometric parameters (Å, º)

Br1—Ni1	2.4058 (11)	C10—H10A	0.9700
Ni1—N1	2.016 (3)	C10—H10B	0.9700
Ni1—N2	2.011 (4)	C10—C11	1.526 (5)
Ni1—C1	1.831 (4)	C11—H11A	0.9700
P1—N1	1.627 (4)	C11—H11B	0.9700
P1—C21	1.845 (4)	C11—C12	1.514 (6)
P1—C15	1.847 (4)	C12—H12A	0.9700
P1—C9	1.806 (5)	C12—H12B	0.9700
P2—N2	1.613 (4)	C12—C13	1.524 (6)
P2—C27	1.856 (5)	C13—H13A	0.9700
P2—C33	1.830 (5)	C13—H13B	0.9700
P2—C39	1.845 (5)	C13—C14	1.528 (6)
N1—C7	1.505 (5)	C14—H14A	0.9700
N2—C8	1.509 (5)	C14—H14B	0.9700
C1—C2	1.382 (6)	C27—H27	0.9800
C1—C6	1.389 (6)	C27—C28	1.533 (6)
C2—C3	1.385 (6)	C27—C32	1.542 (6)
C2—C7	1.496 (6)	C28—H28A	0.9700
C3—H3	0.9300	C28—H28B	0.9700
C3—C4	1.398 (6)	C28—C29	1.518 (6)
C4—H4	0.9300	C29—H29A	0.9700
C4—C5	1.392 (6)	C29—H29B	0.9700
C5—H5	0.9300	C29—C30	1.521 (6)
C5—C6	1.394 (6)	C30—H30A	0.9700
C6—C8	1.502 (6)	C30—H30B	0.9700
C7—H7A	0.9700	C30—C31	1.525 (6)
C7—H7B	0.9700	C31—H31A	0.9700
C8—H8A	0.9700	C31—H31B	0.9700
C8—H8B	0.9700	C31—C32	1.531 (6)
C21—H21	0.9800	C32—H32A	0.9700
C21—C22	1.534 (6)	C32—H32B	0.9700
C21—C26	1.538 (6)	C33—H33	0.9800
C22—H22A	0.9700	C33—C34	1.543 (5)
C22—H22B	0.9700	C33—C38	1.546 (6)
C22—C23	1.525 (6)	C34—H34A	0.9700
C23—H23A	0.9700	C34—H34B	0.9700
C23—H23B	0.9700	C34—C35	1.527 (6)
C23—C24	1.528 (6)	C35—H35A	0.9700
C24—H24A	0.9700	C35—H35B	0.9700
C24—H24B	0.9700	C35—C36	1.527 (6)
C24—C25	1.517 (7)	C36—H36A	0.9700
C25—H25A	0.9700	C36—H36B	0.9700
C25—H25B	0.9700	C36—C37	1.518 (6)
C25—C26	1.530 (6)	C37—H37A	0.9700
C26—H26A	0.9700	C37—H37B	0.9700
C26—H26B	0.9700	C37—C38	1.534 (6)
C15—H15	0.9800	C38—H38A	0.9700
C15—C16	1.537 (5)	C38—H38B	0.9700
C15—C20	1.554 (5)	C39—H39	0.9800
C16—H16A	0.9700	C39—C40	1.532 (6)
C16—H16B	0.9700	C39—C44	1.545 (6)
C16—C17	1.529 (5)	C40—H40A	0.9700
C17—H17A	0.9700	C40—H40B	0.9700
C17—H17B	0.9700	C40—C41	1.528 (6)
C17—C18	1.526 (6)	C41—H41A	0.9700
C18—H18A	0.9700	C41—H41B	0.9700
C18—H18B	0.9700	C41—C42	1.518 (7)
C18—C19	1.522 (6)	C42—H42A	0.9700
C19—H19A	0.9700	C42—H42B	0.9700
C19—H19B	0.9700	C42—C43	1.521 (7)
C19—C20	1.530 (5)	C43—H43A	0.9700
C20—H20A	0.9700	C43—H43B	0.9700
C20—H20B	0.9700	C43—C44	1.531 (6)
C9—C10	1.525 (6)	C44—H44A	0.9700
C9—C14	1.537 (6)	C44—H44B	0.9700
C9—H9	0.81 (5)
N1—Ni1—Br1	104.81 (10)	C11—C10—C9	110.4 (4)
N2—Ni1—Br1	92.66 (11)	C11—C10—H10A	109.6
N2—Ni1—N1	161.95 (14)	C11—C10—H10B	109.6
C1—Ni1—Br1	163.92 (13)	C10—C11—H11A	109.1
C1—Ni1—N1	82.44 (17)	C10—C11—H11B	109.1
C1—Ni1—N2	81.83 (17)	H11A—C11—H11B	107.8
N1—P1—C21	113.1 (2)	C12—C11—C10	112.5 (4)
N1—P1—C15	110.68 (18)	C12—C11—H11A	109.1
N1—P1—C9	110.09 (19)	C12—C11—H11B	109.1
C21—P1—C15	104.30 (19)	C11—C12—H12A	109.3
C9—P1—C21	106.8 (2)	C11—C12—H12B	109.3
C9—P1—C15	111.7 (2)	C11—C12—C13	111.6 (4)
N2—P2—C27	115.9 (2)	H12A—C12—H12B	108.0
N2—P2—C33	108.9 (2)	C13—C12—H12A	109.3
N2—P2—C39	110.1 (2)	C13—C12—H12B	109.3
C33—P2—C27	105.9 (2)	C12—C13—H13A	109.3
C33—P2—C39	111.2 (2)	C12—C13—H13B	109.3
C39—P2—C27	104.8 (2)	C12—C13—C14	111.7 (4)
P1—N1—Ni1	131.97 (19)	H13A—C13—H13B	107.9
C7—N1—Ni1	111.6 (3)	C14—C13—H13A	109.3
C7—N1—P1	115.1 (3)	C14—C13—H13B	109.3
P2—N2—Ni1	120.1 (2)	C9—C14—H14A	109.9
C8—N2—Ni1	107.9 (2)	C9—C14—H14B	109.9
C8—N2—P2	117.6 (3)	C13—C14—C9	109.1 (4)
C2—C1—Ni1	120.4 (3)	C13—C14—H14A	109.9
C2—C1—C6	120.2 (4)	C13—C14—H14B	109.9
C6—C1—Ni1	119.3 (3)	H14A—C14—H14B	108.3
C1—C2—C3	120.4 (4)	P2—C27—H27	107.9
C1—C2—C7	114.0 (4)	C28—C27—P2	111.9 (3)
C3—C2—C7	125.6 (4)	C28—C27—H27	107.9
C2—C3—H3	120.4	C28—C27—C32	111.0 (4)
C2—C3—C4	119.2 (4)	C32—C27—P2	110.2 (3)
C4—C3—H3	120.4	C32—C27—H27	107.9
C3—C4—H4	119.6	C27—C28—H28A	109.0
C5—C4—C3	120.9 (4)	C27—C28—H28B	109.0
C5—C4—H4	119.6	H28A—C28—H28B	107.8
C4—C5—H5	120.6	C29—C28—C27	112.8 (4)
C4—C5—C6	118.9 (4)	C29—C28—H28A	109.0
C6—C5—H5	120.6	C29—C28—H28B	109.0
C1—C6—C5	120.3 (4)	C28—C29—H29A	109.4
C1—C6—C8	112.1 (4)	C28—C29—H29B	109.4
C5—C6—C8	127.5 (4)	C28—C29—C30	111.4 (4)
N1—C7—H7A	110.3	H29A—C29—H29B	108.0
N1—C7—H7B	110.3	C30—C29—H29A	109.4
C2—C7—N1	107.3 (3)	C30—C29—H29B	109.4
C2—C7—H7A	110.3	C29—C30—H30A	109.8
C2—C7—H7B	110.3	C29—C30—H30B	109.8
H7A—C7—H7B	108.5	C29—C30—C31	109.6 (4)
N2—C8—H8A	110.3	H30A—C30—H30B	108.2
N2—C8—H8B	110.3	C31—C30—H30A	109.8
C6—C8—N2	107.2 (3)	C31—C30—H30B	109.8
C6—C8—H8A	110.3	C30—C31—H31A	109.5
C6—C8—H8B	110.3	C30—C31—H31B	109.5
H8A—C8—H8B	108.5	C30—C31—C32	110.9 (4)
P1—C21—H21	107.6	H31A—C31—H31B	108.0
C22—C21—P1	110.8 (3)	C32—C31—H31A	109.5
C22—C21—H21	107.6	C32—C31—H31B	109.5
C22—C21—C26	109.3 (4)	C27—C32—H32A	109.1
C26—C21—P1	113.8 (3)	C27—C32—H32B	109.1
C26—C21—H21	107.6	C31—C32—C27	112.3 (4)
C21—C22—H22A	109.2	C31—C32—H32A	109.1
C21—C22—H22B	109.2	C31—C32—H32B	109.1
H22A—C22—H22B	107.9	H32A—C32—H32B	107.9
C23—C22—C21	112.1 (4)	P2—C33—H33	105.6
C23—C22—H22A	109.2	C34—C33—P2	113.0 (3)
C23—C22—H22B	109.2	C34—C33—H33	105.6
C22—C23—H23A	109.4	C34—C33—C38	109.8 (3)
C22—C23—H23B	109.4	C38—C33—P2	116.4 (3)
C22—C23—C24	111.1 (4)	C38—C33—H33	105.6
H23A—C23—H23B	108.0	C33—C34—H34A	109.6
C24—C23—H23A	109.4	C33—C34—H34B	109.6
C24—C23—H23B	109.4	H34A—C34—H34B	108.2
C23—C24—H24A	109.5	C35—C34—C33	110.1 (4)
C23—C24—H24B	109.5	C35—C34—H34A	109.6
H24A—C24—H24B	108.1	C35—C34—H34B	109.6
C25—C24—C23	110.6 (4)	C34—C35—H35A	109.2
C25—C24—H24A	109.5	C34—C35—H35B	109.2
C25—C24—H24B	109.5	C34—C35—C36	112.0 (4)
C24—C25—H25A	109.3	H35A—C35—H35B	107.9
C24—C25—H25B	109.3	C36—C35—H35A	109.2
C24—C25—C26	111.6 (4)	C36—C35—H35B	109.2
H25A—C25—H25B	108.0	C35—C36—H36A	109.4
C26—C25—H25A	109.3	C35—C36—H36B	109.4
C26—C25—H25B	109.3	H36A—C36—H36B	108.0
C21—C26—H26A	109.4	C37—C36—C35	111.4 (4)
C21—C26—H26B	109.4	C37—C36—H36A	109.4
C25—C26—C21	111.3 (4)	C37—C36—H36B	109.4
C25—C26—H26A	109.4	C36—C37—H37A	109.5
C25—C26—H26B	109.4	C36—C37—H37B	109.5
H26A—C26—H26B	108.0	C36—C37—C38	110.9 (4)
P1—C15—H15	105.5	H37A—C37—H37B	108.0
C16—C15—P1	116.7 (3)	C38—C37—H37A	109.5
C16—C15—H15	105.5	C38—C37—H37B	109.5
C16—C15—C20	108.9 (3)	C33—C38—H38A	109.7
C20—C15—P1	113.7 (3)	C33—C38—H38B	109.7
C20—C15—H15	105.5	C37—C38—C33	110.0 (4)
C15—C16—H16A	109.9	C37—C38—H38A	109.7
C15—C16—H16B	109.9	C37—C38—H38B	109.7
H16A—C16—H16B	108.3	H38A—C38—H38B	108.2
C17—C16—C15	109.0 (3)	P2—C39—H39	105.3
C17—C16—H16A	109.9	C40—C39—P2	115.0 (3)
C17—C16—H16B	109.9	C40—C39—H39	105.3
C16—C17—H17A	109.3	C40—C39—C44	109.7 (4)
C16—C17—H17B	109.3	C44—C39—P2	115.2 (3)
H17A—C17—H17B	107.9	C44—C39—H39	105.3
C18—C17—C16	111.8 (4)	C39—C40—H40A	109.5
C18—C17—H17A	109.3	C39—C40—H40B	109.5
C18—C17—H17B	109.3	H40A—C40—H40B	108.1
C17—C18—H18A	109.4	C41—C40—C39	110.6 (4)
C17—C18—H18B	109.4	C41—C40—H40A	109.5
H18A—C18—H18B	108.0	C41—C40—H40B	109.5
C19—C18—C17	111.2 (4)	C40—C41—H41A	109.4
C19—C18—H18A	109.4	C40—C41—H41B	109.4
C19—C18—H18B	109.4	H41A—C41—H41B	108.0
C18—C19—H19A	109.6	C42—C41—C40	110.9 (5)
C18—C19—H19B	109.6	C42—C41—H41A	109.4
C18—C19—C20	110.2 (4)	C42—C41—H41B	109.4
H19A—C19—H19B	108.1	C41—C42—H42A	109.4
C20—C19—H19A	109.6	C41—C42—H42B	109.4
C20—C19—H19B	109.6	C41—C42—C43	111.2 (4)
C15—C20—H20A	109.7	H42A—C42—H42B	108.0
C15—C20—H20B	109.7	C43—C42—H42A	109.4
C19—C20—C15	110.0 (3)	C43—C42—H42B	109.4
C19—C20—H20A	109.7	C42—C43—H43A	109.2
C19—C20—H20B	109.7	C42—C43—H43B	109.2
H20A—C20—H20B	108.2	C42—C43—C44	112.2 (4)
P1—C9—H9	102 (4)	H43A—C43—H43B	107.9
C10—C9—P1	113.5 (3)	C44—C43—H43A	109.2
C10—C9—C14	111.2 (4)	C44—C43—H43B	109.2
C10—C9—H9	103 (3)	C39—C44—H44A	109.7
C14—C9—P1	117.7 (3)	C39—C44—H44B	109.7
C14—C9—H9	107 (3)	C43—C44—C39	109.8 (4)
C9—C10—H10A	109.6	C43—C44—H44A	109.7
C9—C10—H10B	109.6	C43—C44—H44B	109.7
H10A—C10—H10B	108.1	H44A—C44—H44B	108.2