[6-(4-Bromo­phen­yl)-2,2′-bipyridine-κ2N,N′](tricyclo­hexyl­phosphine-κP)copper(I) tetra­fluoridoborate

Peng, X.-L.

doi:10.1107/S1600536810002965

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page m219

https://doi.org/10.1107/S1600536810002965

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[6-(4-Bromophenyl)-2,2′-bipyridine-κ²N,N′](tricyclohexylphosphine-κP)copper(I) tetrafluoridoborate

Xi-Long Peng ^a ^*

^aSchool of Environmental and Chemical Engineering, Nanchang University, Nanchang 330031, People's Republic of China
^*Correspondence e-mail: jeff_xg@sohu.com

(Received 14 January 2010; accepted 24 January 2010; online 30 January 2010)

In the title compound, [Cu(C₁₆H₁₁BrN₂)(C₁₈H₃₃P)]BF₄, the Cu^I atom is three-coordinated in a distorted trigonal configuration by two N atoms from the 6-(4-bromophenyl)-2,2′-bipyridine ligand and a P atom from the tricyclohexylphosphine ligand. In addition, a weak anion⋯Cu^I interaction with a nearest F⋯Cu separation of 2.696 (5) Å is found.

Related literature

For the rich photophysical properties of opper(I) complexes with diimine and phosphine ligands and their potential applications in organic light-emitting diodes (OLEDs), see: Miller et al. (1999 ); Zhang et al. (2006 ). For related structures, see: Wang et al. (2010 ). For a similar weak anion⋯Cu(I) interaction, see: Mao et al. (2003 ).

Experimental

Crystal data

[Cu(C₁₆H₁₁BrN₂)(C₁₈H₃₃P)]BF₄
M_r = 741.94
Monoclinic, P 2₁ /n
a = 9.8950 (8) Å
b = 20.2114 (17) Å
c = 17.3317 (14) Å
β = 93.010 (1)°
V = 3461.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.88 mm⁻¹
T = 293 K
0.45 × 0.30 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.514, T_max = 0.687
26011 measured reflections
8150 independent reflections
4532 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.151
S = 1.02
8150 reflections
398 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.70 e Å⁻³

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810002965/hg2631sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810002965/hg2631Isup2.hkl

checkCIF report

Comment top

Copper(I) complexes with diimine and phosphine ligands have attracted much attention for their rich photophysical properties and potential applications in organic light-emitting diodes (OLEDs) (Miller et al., 1999; Zhang et al., 2006). These complexes are generally four-coordinate. With bulky phosphine ligands such as tricyclohexylphosphine, three-coordinate complexes have been reported (Wang et al., 2010). We reported here a new three-coordinated copper(I) complex of the title compound, (I).

Compound (I)

The crystal structure of (I) is depicted in Fig. 1. The copper(I) atom is three-coordinated in distorted trigonal configurations by two N atoms from 6-(4-bromo)phenyl-2,2'-bipyridine and a P atom from tricyclohexylphosphine. The coordination angles around the copper(I) atom are 80.029 (11) ° (N1—Cu1—N2), 131.74 (8) ° (N1—Cu1—P1) and 129.43 (7) ° (P1—Cu1—N2) respectively. The Cu—P (2.1811 (9) Å) and Cu—N (2.038 (3) and 2.080 (3) Å) distances are within the normal ranges for related complexes (Wang et al., 2010). In addition, weak anion···Cu(I) interaction is founded, as evidenced by the nearest F···Cu separation of 2.696 (5) Å (Cu1—F1) in the title compound. Similar weak anion···Cu(I) interaction was also reported by Mao et al. (2003).

Related literature top

For the rich photophysical properties of opper(I) complexes with diimine and phosphine ligands and their potential applications in organic light-emitting diodes (OLEDs), see: Miller et al. (1999); Zhang et al. (2006). For related structures, see: Wang et al. (2010). For a similar weak anion···Cu(I) interaction, see: Mao et al. (2003).

Experimental top

The ligand 6-(4-bromo)phenyl-2,2'-bipyridine (L) was prepared by literature method (Wang et al., 2010). A mixture of [Cu(CH₃CN)₄]BF₄ (100 mg, 0.32 mmol) and L (99 mg, 0.32 mmol) in dichloromethane (20 ml) was stirred under nitrogen atmosphere at room temperature for 2 h. Then tricyclohexylphosphine (89 mg, 0.32 mmol) was added kept stirring for 2 h. The solvents were removed and the solid residue was afforded. Yellow single crystals suitable for X-ray diffraction were obtained from the solution of dichloromethane by vapor diffusion with diethyl ether (yield: 82%). Analysis calculated for [Cu(C₁₆H₁₁N₂Br)(C₁₈H₃₃P)].(BF₄): C 53.38, H 5.93 N 3.77%; Found: C 53.92, H 5.63, 3.57%.

Structure description top

Compound (I)

For the rich photophysical properties of opper(I) complexes with diimine and phosphine ligands and their potential applications in organic light-emitting diodes (OLEDs), see: Miller et al. (1999); Zhang et al. (2006). For related structures, see: Wang et al. (2010). For a similar weak anion···Cu(I) interaction, see: Mao et al. (2003).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. : The molecular structure of compound (I). Displacement ellipsoids are drawn at the 30% probability level, and all hydrogen atoms are omitted for clarity.

[6-(4-Bromophenyl)-2,2'-bipyridine- κ²N,N'](tricyclohexylphosphine-κP)copper(I) tetrafluoridoborate top

Crystal data top

[Cu(C₁₆H₁₁BrN₂)(C₁₈H₃₃P)]BF₄	F(000) = 1528
M_r = 741.94	D_x = 1.424 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 892 reflections
a = 9.8950 (8) Å	θ = 2.2–25.8°
b = 20.2114 (17) Å	µ = 1.88 mm⁻¹
c = 17.3317 (14) Å	T = 293 K
β = 93.010 (1)°	Block, yellow
V = 3461.4 (5) Å³	0.45 × 0.30 × 0.20 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	8150 independent reflections
Radiation source: fine-focus sealed tube	4532 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
phi and ω scans	θ_max = 28.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −13→13
T_min = 0.514, T_max = 0.687	k = −26→26
26011 measured reflections	l = −23→21

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.059P)² + 1.0457P] where P = (F_o² + 2F_c²)/3
8150 reflections	(Δ/σ)_max = 0.012
398 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.70 e Å⁻³

Crystal data top

[Cu(C₁₆H₁₁BrN₂)(C₁₈H₃₃P)]BF₄	V = 3461.4 (5) Å³
M_r = 741.94	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.8950 (8) Å	µ = 1.88 mm⁻¹
b = 20.2114 (17) Å	T = 293 K
c = 17.3317 (14) Å	0.45 × 0.30 × 0.20 mm
β = 93.010 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	8150 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	4532 reflections with I > 2σ(I)
T_min = 0.514, T_max = 0.687	R_int = 0.043
26011 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 1.02	Δρ_max = 0.36 e Å⁻³
8150 reflections	Δρ_min = −0.70 e Å⁻³
398 parameters

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. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² 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 (Å²) top

	x	y	z	U_iso*/U_eq
Cu1	0.68710 (4)	0.11177 (2)	0.13751 (2)	0.05341 (15)
P1	0.77547 (9)	0.19570 (4)	0.20113 (5)	0.0467 (2)
Br1	0.78459 (6)	0.00217 (4)	0.49674 (3)	0.1190 (3)
N2	0.4943 (3)	0.07131 (12)	0.14102 (15)	0.0469 (6)
N1	0.6442 (3)	0.09700 (14)	0.02248 (16)	0.0542 (7)
C1	0.8915 (5)	0.24251 (19)	0.1413 (3)	0.0848 (14)
H1A	0.9664	0.2341	0.1792	0.102*
C2	0.9125 (5)	0.3136 (2)	0.1498 (3)	0.0845 (13)
H2A	0.9489	0.3218	0.2020	0.101*
H2B	0.8248	0.3350	0.1446	0.101*
C3	1.0017 (6)	0.3458 (2)	0.0961 (4)	0.117 (2)
H3A	0.9493	0.3805	0.0700	0.140*
H3B	1.0730	0.3675	0.1272	0.140*
C4	1.0649 (6)	0.3095 (3)	0.0385 (3)	0.118 (2)
H4A	1.1614	0.3176	0.0454	0.142*
H4B	1.0355	0.3286	−0.0110	0.142*
C5	1.0469 (5)	0.2393 (3)	0.0321 (3)	0.0971 (16)
H5A	1.1355	0.2189	0.0382	0.117*
H5B	1.0120	0.2298	−0.0201	0.117*
C6	0.9594 (6)	0.2066 (2)	0.0848 (3)	0.1063 (19)
H6A	0.8906	0.1834	0.0535	0.128*
H6B	1.0135	0.1731	0.1121	0.128*
C7	0.6381 (3)	0.25423 (16)	0.22294 (19)	0.0517 (8)
H7A	0.6789	0.2952	0.2435	0.062*
C8	0.5519 (4)	0.2706 (2)	0.1495 (2)	0.0724 (11)
H8A	0.6081	0.2920	0.1127	0.087*
H8B	0.5174	0.2299	0.1263	0.087*
C13	0.8643 (3)	0.17867 (16)	0.29569 (18)	0.0515 (8)
H13A	0.7983	0.1551	0.3257	0.062*
C24	0.4262 (4)	0.07942 (15)	0.07240 (19)	0.0509 (8)
C28	0.4265 (3)	0.05544 (15)	0.2040 (2)	0.0510 (8)
C29	0.5105 (4)	0.04185 (16)	0.27528 (19)	0.0510 (8)
C23	0.5110 (4)	0.09002 (15)	0.00546 (19)	0.0517 (8)
C33	0.7185 (4)	0.00015 (19)	0.3355 (2)	0.0668 (10)
H33A	0.8025	−0.0200	0.3318	0.080*
F2	0.8170 (3)	−0.09236 (13)	0.17853 (19)	0.1044 (9)
C19	0.7271 (4)	0.10229 (19)	−0.0355 (2)	0.0651 (10)
H19A	0.8196	0.1055	−0.0237	0.078*
C34	0.6373 (4)	0.01317 (17)	0.2707 (2)	0.0583 (9)
H34A	0.6680	0.0025	0.2224	0.070*
C22	0.4591 (4)	0.09145 (17)	−0.0705 (2)	0.0631 (10)
H22A	0.3664	0.0878	−0.0817	0.076*
C27	0.2865 (4)	0.05087 (18)	0.1998 (2)	0.0635 (10)
H27A	0.2403	0.0409	0.2437	0.076*
C32	0.6723 (5)	0.0178 (2)	0.4065 (2)	0.0713 (11)
C12	0.5487 (4)	0.22462 (19)	0.2837 (2)	0.0649 (10)
H12A	0.5164	0.1816	0.2663	0.078*
H12B	0.6024	0.2184	0.3316	0.078*
C18	0.9811 (4)	0.1305 (2)	0.2887 (2)	0.0670 (10)
H18A	0.9492	0.0916	0.2606	0.080*
H18B	1.0508	0.1511	0.2596	0.080*
C14	0.9064 (5)	0.23832 (19)	0.3445 (2)	0.0720 (11)
H14A	0.9728	0.2639	0.3181	0.086*
H14B	0.8282	0.2663	0.3512	0.086*
C30	0.4678 (4)	0.05694 (17)	0.3477 (2)	0.0625 (10)
H30A	0.3826	0.0755	0.3520	0.075*
C17	1.0409 (5)	0.1100 (2)	0.3669 (2)	0.0748 (11)
H17A	1.1191	0.0820	0.3602	0.090*
H17B	0.9747	0.0843	0.3934	0.090*
C26	0.2172 (4)	0.06113 (19)	0.1308 (2)	0.0696 (11)
H26A	0.1232	0.0588	0.1277	0.084*
C20	0.6821 (5)	0.10323 (18)	−0.1120 (2)	0.0718 (11)
H20A	0.7427	0.1071	−0.1510	0.086*
F1	0.8562 (3)	0.00766 (13)	0.12988 (18)	0.1024 (9)
B1	0.9142 (5)	−0.0521 (3)	0.1505 (3)	0.0689 (12)
C15	0.9660 (6)	0.2171 (2)	0.4231 (2)	0.0899 (15)
H15A	0.9973	0.2559	0.4519	0.108*
H15B	0.8963	0.1960	0.4518	0.108*
C31	0.5477 (5)	0.04533 (19)	0.4138 (2)	0.0697 (11)
H31A	0.5174	0.0560	0.4621	0.084*
C25	0.2863 (4)	0.07504 (19)	0.0657 (2)	0.0656 (10)
H25A	0.2400	0.0813	0.0182	0.079*
C21	0.5465 (5)	0.09833 (18)	−0.1291 (2)	0.0731 (12)
H21A	0.5131	0.0996	−0.1803	0.088*
F4	1.0131 (3)	−0.04289 (16)	0.20553 (19)	0.1233 (11)
C11	0.4289 (4)	0.2684 (2)	0.2986 (3)	0.0807 (12)
H11A	0.4609	0.3092	0.3227	0.097*
H11B	0.3715	0.2462	0.3342	0.097*
F3	0.9654 (4)	−0.07998 (18)	0.08765 (19)	0.1367 (12)
C16	1.0830 (5)	0.1695 (2)	0.4158 (3)	0.0908 (14)
H16A	1.1148	0.1548	0.4668	0.109*
H16B	1.1569	0.1922	0.3925	0.109*
C10	0.3467 (5)	0.2845 (3)	0.2250 (3)	0.1079 (19)
H10A	0.3059	0.2443	0.2039	0.130*
H10B	0.2745	0.3148	0.2365	0.130*
C9	0.4344 (5)	0.3154 (3)	0.1659 (3)	0.0993 (16)
H9A	0.4686	0.3576	0.1850	0.119*
H9B	0.3805	0.3234	0.1184	0.119*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0505 (3)	0.0598 (3)	0.0497 (3)	−0.0065 (2)	0.00034 (18)	−0.00971 (18)
P1	0.0461 (5)	0.0488 (5)	0.0448 (5)	−0.0027 (4)	−0.0008 (4)	−0.0016 (4)
Br1	0.1016 (5)	0.1800 (6)	0.0738 (4)	−0.0118 (4)	−0.0103 (3)	0.0430 (3)
N2	0.0463 (16)	0.0445 (14)	0.0495 (16)	−0.0020 (12)	−0.0010 (13)	−0.0071 (11)
N1	0.0588 (19)	0.0575 (17)	0.0464 (15)	−0.0013 (14)	0.0040 (14)	−0.0103 (12)
C1	0.104 (4)	0.055 (2)	0.100 (3)	−0.006 (2)	0.050 (3)	0.005 (2)
C2	0.103 (4)	0.061 (2)	0.091 (3)	−0.020 (2)	0.021 (3)	0.004 (2)
C3	0.128 (5)	0.071 (3)	0.158 (6)	−0.007 (3)	0.062 (4)	0.027 (3)
C4	0.131 (5)	0.112 (4)	0.117 (4)	−0.028 (4)	0.056 (4)	0.021 (3)
C5	0.106 (4)	0.097 (4)	0.092 (3)	0.006 (3)	0.043 (3)	0.017 (3)
C6	0.131 (5)	0.083 (3)	0.111 (4)	−0.030 (3)	0.065 (4)	−0.021 (3)
C7	0.048 (2)	0.0499 (18)	0.0562 (19)	0.0000 (15)	−0.0035 (15)	−0.0059 (15)
C8	0.066 (3)	0.086 (3)	0.064 (2)	0.014 (2)	−0.009 (2)	−0.004 (2)
C13	0.053 (2)	0.0535 (19)	0.0472 (19)	−0.0032 (16)	−0.0035 (15)	−0.0024 (14)
C24	0.052 (2)	0.0411 (17)	0.058 (2)	0.0029 (15)	−0.0029 (16)	−0.0088 (14)
C28	0.051 (2)	0.0431 (18)	0.060 (2)	0.0009 (15)	0.0083 (16)	−0.0058 (15)
C29	0.053 (2)	0.0465 (18)	0.054 (2)	−0.0054 (16)	0.0124 (16)	−0.0032 (14)
C23	0.059 (2)	0.0389 (17)	0.056 (2)	−0.0003 (15)	−0.0055 (17)	−0.0051 (14)
C33	0.059 (2)	0.074 (3)	0.068 (3)	0.0010 (19)	0.008 (2)	0.0142 (19)
F2	0.0653 (16)	0.0881 (17)	0.160 (3)	−0.0037 (14)	0.0074 (17)	0.0175 (17)
C19	0.069 (3)	0.072 (2)	0.054 (2)	−0.0079 (19)	0.0067 (19)	−0.0102 (17)
C34	0.057 (2)	0.061 (2)	0.058 (2)	−0.0032 (18)	0.0107 (18)	−0.0006 (16)
C22	0.074 (3)	0.057 (2)	0.056 (2)	0.0006 (18)	−0.0167 (19)	−0.0014 (16)
C27	0.053 (2)	0.066 (2)	0.073 (3)	0.0020 (18)	0.014 (2)	−0.0090 (18)
C32	0.078 (3)	0.078 (3)	0.059 (2)	−0.014 (2)	0.001 (2)	0.0165 (19)
C12	0.063 (2)	0.064 (2)	0.069 (2)	0.0038 (19)	0.0127 (19)	−0.0100 (18)
C18	0.063 (3)	0.078 (3)	0.059 (2)	0.012 (2)	−0.0071 (19)	0.0004 (18)
C14	0.092 (3)	0.061 (2)	0.061 (2)	0.001 (2)	−0.022 (2)	−0.0081 (18)
C30	0.065 (2)	0.061 (2)	0.063 (2)	0.0029 (18)	0.0165 (19)	−0.0004 (17)
C17	0.069 (3)	0.088 (3)	0.067 (3)	0.019 (2)	−0.006 (2)	0.009 (2)
C26	0.045 (2)	0.073 (3)	0.091 (3)	−0.0029 (19)	0.003 (2)	−0.006 (2)
C20	0.101 (4)	0.061 (2)	0.054 (2)	−0.008 (2)	0.012 (2)	−0.0045 (17)
F1	0.104 (2)	0.0866 (17)	0.118 (2)	0.0332 (15)	0.0251 (17)	0.0238 (15)
B1	0.051 (3)	0.076 (3)	0.081 (3)	0.007 (2)	0.009 (2)	0.000 (2)
C15	0.133 (4)	0.078 (3)	0.055 (2)	0.000 (3)	−0.028 (3)	−0.004 (2)
C31	0.087 (3)	0.071 (2)	0.052 (2)	−0.008 (2)	0.014 (2)	0.0030 (18)
C25	0.055 (2)	0.063 (2)	0.077 (3)	0.0020 (18)	−0.0142 (19)	−0.0041 (19)
C21	0.117 (4)	0.054 (2)	0.046 (2)	0.001 (2)	−0.012 (2)	−0.0041 (16)
F4	0.099 (2)	0.130 (2)	0.135 (3)	−0.0346 (19)	−0.0452 (19)	0.0268 (19)
C11	0.062 (3)	0.095 (3)	0.085 (3)	0.009 (2)	0.012 (2)	−0.024 (2)
F3	0.137 (3)	0.155 (3)	0.121 (3)	0.051 (2)	0.036 (2)	−0.024 (2)
C16	0.083 (3)	0.108 (4)	0.077 (3)	−0.010 (3)	−0.032 (2)	0.016 (3)
C10	0.059 (3)	0.156 (5)	0.108 (4)	0.033 (3)	−0.009 (3)	−0.044 (4)
C9	0.086 (4)	0.121 (4)	0.087 (3)	0.047 (3)	−0.027 (3)	−0.014 (3)

Geometric parameters (Å, º) top

Cu1—N1	2.038 (3)	F2—B1	1.368 (5)
Cu1—N2	2.080 (3)	C19—C20	1.376 (5)
Cu1—P1	2.1811 (9)	C19—H19A	0.9300
P1—C1	1.848 (4)	C34—H34A	0.9300
P1—C13	1.851 (3)	C22—C21	1.375 (6)
P1—C7	1.855 (3)	C22—H22A	0.9300
Br1—C32	1.896 (4)	C27—C26	1.362 (5)
N2—C24	1.346 (4)	C27—H27A	0.9300
N2—C28	1.349 (4)	C32—C31	1.365 (6)
N1—C19	1.335 (4)	C12—C11	1.512 (5)
N1—C23	1.342 (4)	C12—H12A	0.9700
C1—C6	1.416 (5)	C12—H12B	0.9700
C1—C2	1.457 (5)	C18—C17	1.507 (5)
C1—H1A	0.9800	C18—H18A	0.9700
C2—C3	1.468 (6)	C18—H18B	0.9700
C2—H2A	0.9700	C14—C15	1.518 (5)
C2—H2B	0.9700	C14—H14A	0.9700
C3—C4	1.412 (7)	C14—H14B	0.9700
C3—H3A	0.9700	C30—C31	1.377 (6)
C3—H3B	0.9700	C30—H30A	0.9300
C4—C5	1.434 (7)	C17—C16	1.519 (6)
C4—H4A	0.9700	C17—H17A	0.9700
C4—H4B	0.9700	C17—H17B	0.9700
C5—C6	1.451 (6)	C26—C25	1.380 (5)
C5—H5A	0.9700	C26—H26A	0.9300
C5—H5B	0.9700	C20—C21	1.362 (6)
C6—H6A	0.9700	C20—H20A	0.9300
C6—H6B	0.9700	F1—B1	1.376 (5)
C7—C12	1.532 (5)	B1—F4	1.343 (6)
C7—C8	1.531 (5)	B1—F3	1.349 (5)
C7—H7A	0.9800	C15—C16	1.515 (7)
C8—C9	1.512 (6)	C15—H15A	0.9700
C8—H8A	0.9700	C15—H15B	0.9700
C8—H8B	0.9700	C31—H31A	0.9300
C13—C14	1.519 (5)	C25—H25A	0.9300
C13—C18	1.520 (5)	C21—H21A	0.9300
C13—H13A	0.9800	C11—C10	1.512 (7)
C24—C25	1.385 (5)	C11—H11A	0.9700
C24—C23	1.483 (5)	C11—H11B	0.9700
C28—C27	1.386 (5)	C16—H16A	0.9700
C28—C29	1.479 (5)	C16—H16B	0.9700
C29—C30	1.379 (5)	C10—C9	1.513 (7)
C29—C34	1.388 (5)	C10—H10A	0.9700
C23—C22	1.389 (5)	C10—H10B	0.9700
C33—C34	1.372 (5)	C9—H9A	0.9700
C33—C32	1.382 (6)	C9—H9B	0.9700
C33—H33A	0.9300

N1—Cu1—N2	80.02 (11)	C29—C34—H34A	119.2
N1—Cu1—P1	131.74 (8)	C21—C22—C23	119.1 (4)
N2—Cu1—P1	129.43 (7)	C21—C22—H22A	120.4
C1—P1—C13	108.2 (2)	C23—C22—H22A	120.4
C1—P1—C7	105.74 (18)	C26—C27—C28	119.5 (4)
C13—P1—C7	104.91 (15)	C26—C27—H27A	120.3
C1—P1—Cu1	111.03 (15)	C28—C27—H27A	120.3
C13—P1—Cu1	117.53 (11)	C31—C32—C33	122.0 (4)
C7—P1—Cu1	108.68 (11)	C31—C32—Br1	119.0 (3)
C24—N2—C28	119.8 (3)	C33—C32—Br1	119.0 (3)
C24—N2—Cu1	110.1 (2)	C11—C12—C7	112.0 (3)
C28—N2—Cu1	127.8 (2)	C11—C12—H12A	109.2
C19—N1—C23	118.5 (3)	C7—C12—H12A	109.2
C19—N1—Cu1	128.3 (3)	C11—C12—H12B	109.2
C23—N1—Cu1	112.5 (2)	C7—C12—H12B	109.2
C6—C1—C2	120.3 (4)	H12A—C12—H12B	107.9
C6—C1—P1	117.2 (3)	C17—C18—C13	111.7 (3)
C2—C1—P1	122.5 (3)	C17—C18—H18A	109.3
C6—C1—H1A	90.3	C13—C18—H18A	109.3
C2—C1—H1A	90.3	C17—C18—H18B	109.3
P1—C1—H1A	90.3	C13—C18—H18B	109.3
C1—C2—C3	117.5 (4)	H18A—C18—H18B	107.9
C1—C2—H2A	107.9	C15—C14—C13	111.0 (3)
C3—C2—H2A	107.9	C15—C14—H14A	109.4
C1—C2—H2B	107.9	C13—C14—H14A	109.4
C3—C2—H2B	107.9	C15—C14—H14B	109.4
H2A—C2—H2B	107.2	C13—C14—H14B	109.4
C4—C3—C2	121.4 (4)	H14A—C14—H14B	108.0
C4—C3—H3A	107.0	C31—C30—C29	122.0 (4)
C2—C3—H3A	107.0	C31—C30—H30A	119.0
C4—C3—H3B	107.0	C29—C30—H30A	119.0
C2—C3—H3B	107.0	C18—C17—C16	111.5 (3)
H3A—C3—H3B	106.7	C18—C17—H17A	109.3
C3—C4—C5	120.8 (4)	C16—C17—H17A	109.3
C3—C4—H4A	107.1	C18—C17—H17B	109.3
C5—C4—H4A	107.1	C16—C17—H17B	109.3
C3—C4—H4B	107.1	H17A—C17—H17B	108.0
C5—C4—H4B	107.1	C27—C26—C25	120.0 (4)
H4A—C4—H4B	106.8	C27—C26—H26A	120.0
C4—C5—C6	118.5 (4)	C25—C26—H26A	120.0
C4—C5—H5A	107.7	C21—C20—C19	118.3 (4)
C6—C5—H5A	107.7	C21—C20—H20A	120.9
C4—C5—H5B	107.7	C19—C20—H20A	120.9
C6—C5—H5B	107.7	F4—B1—F3	109.9 (4)
H5A—C5—H5B	107.1	F4—B1—F2	109.3 (4)
C1—C6—C5	121.6 (4)	F3—B1—F2	109.8 (4)
C1—C6—H6A	106.9	F4—B1—F1	110.0 (4)
C5—C6—H6A	106.9	F3—B1—F1	109.0 (4)
C1—C6—H6B	106.9	F2—B1—F1	108.8 (4)
C5—C6—H6B	106.9	C16—C15—C14	111.5 (4)
H6A—C6—H6B	106.7	C16—C15—H15A	109.3
C12—C7—C8	109.8 (3)	C14—C15—H15A	109.3
C12—C7—P1	110.3 (2)	C16—C15—H15B	109.3
C8—C7—P1	110.5 (2)	C14—C15—H15B	109.3
C12—C7—H7A	108.7	H15A—C15—H15B	108.0
C8—C7—H7A	108.7	C32—C31—C30	118.3 (4)
P1—C7—H7A	108.7	C32—C31—H31A	120.8
C9—C8—C7	111.9 (3)	C30—C31—H31A	120.8
C9—C8—H8A	109.2	C26—C25—C24	118.7 (4)
C7—C8—H8A	109.2	C26—C25—H25A	120.6
C9—C8—H8B	109.2	C24—C25—H25A	120.6
C7—C8—H8B	109.2	C20—C21—C22	119.8 (4)
H8A—C8—H8B	107.9	C20—C21—H21A	120.1
C14—C13—C18	111.4 (3)	C22—C21—H21A	120.1
C14—C13—P1	116.7 (2)	C12—C11—C10	111.9 (3)
C18—C13—P1	112.1 (2)	C12—C11—H11A	109.2
C14—C13—H13A	105.1	C10—C11—H11A	109.2
C18—C13—H13A	105.1	C12—C11—H11B	109.2
P1—C13—H13A	105.1	C10—C11—H11B	109.2
N2—C24—C25	121.2 (3)	H11A—C11—H11B	107.9
N2—C24—C23	115.5 (3)	C15—C16—C17	111.2 (4)
C25—C24—C23	123.2 (3)	C15—C16—H16A	109.4
N2—C28—C27	120.7 (3)	C17—C16—H16A	109.4
N2—C28—C29	116.0 (3)	C15—C16—H16B	109.4
C27—C28—C29	123.2 (3)	C17—C16—H16B	109.4
C30—C29—C34	117.7 (3)	H16A—C16—H16B	108.0
C30—C29—C28	122.3 (3)	C9—C10—C11	111.0 (4)
C34—C29—C28	120.0 (3)	C9—C10—H10A	109.4
N1—C23—C22	121.1 (3)	C11—C10—H10A	109.4
N1—C23—C24	115.6 (3)	C9—C10—H10B	109.4
C22—C23—C24	123.3 (3)	C11—C10—H10B	109.4
C34—C33—C32	118.2 (4)	H10A—C10—H10B	108.0
C34—C33—H33A	120.9	C10—C9—C8	110.7 (4)
C32—C33—H33A	120.9	C10—C9—H9A	109.5
N1—C19—C20	123.1 (4)	C8—C9—H9A	109.5
N1—C19—H19A	118.5	C10—C9—H9B	109.5
C20—C19—H19A	118.5	C8—C9—H9B	109.5
C33—C34—C29	121.7 (3)	H9A—C9—H9B	108.1
C33—C34—H34A	119.2

N1—Cu1—P1—C1	−29.0 (2)	N2—C28—C29—C30	147.1 (3)
N2—Cu1—P1—C1	−144.6 (2)	C27—C28—C29—C30	−34.5 (5)
N1—Cu1—P1—C13	−154.23 (16)	N2—C28—C29—C34	−32.6 (4)
N2—Cu1—P1—C13	90.12 (16)	C27—C28—C29—C34	145.7 (3)
N1—Cu1—P1—C7	86.93 (16)	C19—N1—C23—C22	−3.1 (5)
N2—Cu1—P1—C7	−28.73 (15)	Cu1—N1—C23—C22	168.3 (3)
N1—Cu1—N2—C24	−22.3 (2)	C19—N1—C23—C24	175.6 (3)
P1—Cu1—N2—C24	114.66 (19)	Cu1—N1—C23—C24	−13.0 (3)
N1—Cu1—N2—C28	175.3 (3)	N2—C24—C23—N1	−6.6 (4)
P1—Cu1—N2—C28	−47.8 (3)	C25—C24—C23—N1	176.2 (3)
N2—Cu1—N1—C19	−170.5 (3)	N2—C24—C23—C22	172.1 (3)
P1—Cu1—N1—C19	54.4 (3)	C25—C24—C23—C22	−5.1 (5)
N2—Cu1—N1—C23	19.1 (2)	C23—N1—C19—C20	2.3 (5)
P1—Cu1—N1—C23	−115.9 (2)	Cu1—N1—C19—C20	−167.5 (3)
C13—P1—C1—C6	100.5 (5)	C32—C33—C34—C29	−1.5 (5)
C7—P1—C1—C6	−147.6 (4)	C30—C29—C34—C33	−0.1 (5)
Cu1—P1—C1—C6	−29.9 (5)	C28—C29—C34—C33	179.6 (3)
C13—P1—C1—C2	−80.5 (5)	N1—C23—C22—C21	1.8 (5)
C7—P1—C1—C2	31.5 (5)	C24—C23—C22—C21	−176.8 (3)
Cu1—P1—C1—C2	149.2 (4)	N2—C28—C27—C26	1.4 (5)
C6—C1—C2—C3	2.2 (8)	C29—C28—C27—C26	−176.9 (3)
P1—C1—C2—C3	−176.8 (4)	C34—C33—C32—C31	2.2 (6)
C1—C2—C3—C4	−0.1 (9)	C34—C33—C32—Br1	−178.5 (3)
C2—C3—C4—C5	−1.8 (10)	C8—C7—C12—C11	−53.4 (4)
C3—C4—C5—C6	1.6 (10)	P1—C7—C12—C11	−175.5 (3)
C2—C1—C6—C5	−2.5 (9)	C14—C13—C18—C17	54.7 (4)
P1—C1—C6—C5	176.6 (5)	P1—C13—C18—C17	−172.4 (3)
C4—C5—C6—C1	0.6 (9)	C18—C13—C14—C15	−54.7 (5)
C1—P1—C7—C12	−170.3 (3)	P1—C13—C14—C15	174.7 (3)
C13—P1—C7—C12	−56.1 (3)	C34—C29—C30—C31	1.0 (5)
Cu1—P1—C7—C12	70.4 (3)	C28—C29—C30—C31	−178.7 (3)
C1—P1—C7—C8	68.0 (3)	C13—C18—C17—C16	−54.7 (5)
C13—P1—C7—C8	−177.7 (3)	C28—C27—C26—C25	0.9 (6)
Cu1—P1—C7—C8	−51.2 (3)	N1—C19—C20—C21	−0.2 (6)
C12—C7—C8—C9	55.1 (5)	C13—C14—C15—C16	55.3 (5)
P1—C7—C8—C9	177.0 (3)	C33—C32—C31—C30	−1.4 (6)
C1—P1—C13—C14	62.4 (3)	Br1—C32—C31—C30	179.4 (3)
C7—P1—C13—C14	−50.2 (3)	C29—C30—C31—C32	−0.3 (6)
Cu1—P1—C13—C14	−171.0 (3)	C27—C26—C25—C24	−1.2 (6)
C1—P1—C13—C18	−67.9 (3)	N2—C24—C25—C26	−0.9 (5)
C7—P1—C13—C18	179.6 (3)	C23—C24—C25—C26	176.1 (3)
Cu1—P1—C13—C18	58.8 (3)	C19—C20—C21—C22	−1.2 (6)
C28—N2—C24—C25	3.3 (5)	C23—C22—C21—C20	0.4 (5)
Cu1—N2—C24—C25	−160.8 (3)	C7—C12—C11—C10	54.4 (5)
C28—N2—C24—C23	−174.0 (3)	C14—C15—C16—C17	−55.4 (5)
Cu1—N2—C24—C23	21.9 (3)	C18—C17—C16—C15	55.0 (5)
C24—N2—C28—C27	−3.5 (5)	C12—C11—C10—C9	−55.5 (6)
Cu1—N2—C28—C27	157.4 (2)	C11—C10—C9—C8	56.5 (6)
C24—N2—C28—C29	174.9 (3)	C7—C8—C9—C10	−57.2 (5)
Cu1—N2—C28—C29	−24.2 (4)

Experimental details

Crystal data
Chemical formula	[Cu(C₁₆H₁₁BrN₂)(C₁₈H₃₃P)]BF₄
M_r	741.94
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	9.8950 (8), 20.2114 (17), 17.3317 (14)
β (°)	93.010 (1)
V (Å³)	3461.4 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.88
Crystal size (mm)	0.45 × 0.30 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.514, 0.687
No. of measured, independent and observed [I > 2σ(I)] reflections	26011, 8150, 4532
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.151, 1.02
No. of reflections	8150
No. of parameters	398
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.70

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

References

Bruker (1998). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Mao, Z., Chao, H.-Y., Hui, Z., Che, C.-M., Fu, W.-F., Cheung, K.-K. & Zhu, N. (2003). Chem. Eur. J. 9, 2885–2997. Web of Science CSD CrossRef PubMed CAS Google Scholar
Miller, M. T., Gantzel, P. K. & Karpishin, T. B. (1999). J. Am. Chem. Soc. 121, 4292–4293. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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