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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): m1019.
Published online 2008 July 9. doi:  10.1107/S1600536808020679
PMCID: PMC2961942

Bis{2-[(4-bromo­phen­yl)imino­meth­yl]pyridine-κ2 N,N′}copper(I) tetra­phenyl­borate

Abstract

In the crystal structure of the title compound, [Cu(C12H9BrN2)2](C24H20B), the copper(I) cation is coordinated by four N atoms of two crystallographically independent 2-[(4-bromo­phen­yl)imino­meth­yl]pyridine ligands within a distorted tetra­hedron.

Related literature

For applications of imino­pyridine complexes, see: Armaroli (2001 [triangle]); Sakaki et al. (2002 [triangle]). For related structures, see Dehghanpour & Mahmoudi (2007 [triangle]); Dehghanpour et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1019-scheme1.jpg

Experimental

Crystal data

  • [Cu(C12H9BrN2)2](C24H20B)
  • M r = 904.99
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1019-efi1.jpg
  • a = 11.7198 (10) Å
  • b = 13.1527 (11) Å
  • c = 14.4735 (12) Å
  • α = 80.5034 (9)°
  • β = 69.3835 (8)°
  • γ = 89.5465 (9)°
  • V = 2056.5 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 2.51 mm−1
  • T = 193 (2) K
  • 0.67 × 0.37 × 0.34 mm

Data collection

  • Bruker SMART 1000 CCD area-detector/PLATFORM diffractometer
  • Absorption correction: integration (SHELXTL; Sheldrick, 2008 [triangle]) T min = 0.339, T max = 0.423
  • 17095 measured reflections
  • 9230 independent reflections
  • 7124 reflections with I > 2σ(I)
  • R int = 0.022

Refinement

  • R[F 2 > 2σ(F 2)] = 0.033
  • wR(F 2) = 0.079
  • S = 1.03
  • 9230 reflections
  • 505 parameters
  • H-atom parameters constrained
  • Δρmax = 0.70 e Å−3
  • Δρmin = −0.39 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808020679/nc2107sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020679/nc2107Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

SD acknowledges the Alzahra University Research Council for partial support of this work.

supplementary crystallographic information

Comment

Much interest has recently been focused on the rational design and construction of novel copper(I) complexes because of their reversible electrochemical behavior, light absorption in the visible spectral region; characteristic structural flexibility, long-lived electronically excited states, intense luminescence and ease of preparation (Armaroli, 2001; Sakaki et al., 2002). In continuation of our interests on this topic (Dehghanpour et al., 2007; Dehghanpour & Mahmoudi, 2007), we report herein the X-ray crystal structure of the copper(I) complex of the Schiff base ligand of (4-bromo-phenyl)-pyridin-2-ylmethylene-amine.

The structure of (I) consists of discrete [(C12H9BrN2)2Cu]+ cations and [BPh4]- anions (Fig. 1). The copper(I) cation centre has a tetrahedral coordination which shows signficant distortion, mainly due to the presence of the five-membered chelate ring (Table 1). The endocyclic N1—Cu—N2 angle is much smaller than the ideal tetrahedral angle of 109.5°, whereas the opposite N1—Cu—N4 angle is much wider than the ideal tetrahedral angle.

Experimental

To a solution of (4-bromo-phenyl)-pyridin-2-ylmethylene-amine (37.8 mg, 0.1 mmol) in 20 ml acetonitrile copper tetraphenylborate (28.9 mg, 0.1 mmol)was added . The mixture was heated to dissolve the reactants, filtered off and the solvent was removed under vacuum to about 5 ml. The diffusion of diethyl ether vapor into the solution leads to light-yellow crystals. The crystals were collected and washed with diethylether. yield 83%. Calc. for C48H38BBr2CuN4: C 63.70, H 4.23, N 6.19%; found: C 63.73, H 4.21, N 6.17%.

Refinement

All hydrogen atoms were placed in geometrically calculated positions and refined isotropic using a riding model with Uiso(H) equal to 1.2Ueq(C).

Figures

Fig. 1.
Crystal structure of the cation (a) and the anion (b) with labeling and thermal ellipsoids drawn at 50% the probability level. Hydrogen atoms are shown as spheres of arbitrary radius.

Crystal data

[Cu(C12H9BrN2)2](C24H20B)Z = 2
Mr = 904.99F000 = 916
Triclinic, P1Dx = 1.461 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 11.7198 (10) ÅCell parameters from 7821 reflections
b = 13.1527 (11) Åθ = 2.4–27.3º
c = 14.4735 (12) ŵ = 2.51 mm1
α = 80.5034 (9)ºT = 193 (2) K
β = 69.3835 (8)ºPrism, brown
γ = 89.5465 (9)º0.67 × 0.37 × 0.34 mm
V = 2056.5 (3) Å3

Data collection

Bruker SMART 1000 CCD area-detector/PLATFORM diffractometer9230 independent reflections
Radiation source: fine-focus sealed tube7124 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.022
Detector resolution: 8.192 pixels mm-1θmax = 27.5º
T = 193(2) Kθmin = 1.6º
ω scansh = −15→15
Absorption correction: integration(SHELXTL; Sheldrick, 2008)k = −17→17
Tmin = 0.339, Tmax = 0.423l = −18→18
17095 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.079  w = 1/[σ2(Fo2) + (0.0381P)2 + 0.4988P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
9230 reflectionsΔρmax = 0.70 e Å3
505 parametersΔρmin = −0.39 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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)

xyzUiso*/Ueq
Br10.49211 (2)−0.06504 (2)0.16116 (2)0.04820 (8)
Br20.47991 (2)0.72688 (2)−0.05911 (2)0.05109 (8)
Cu0.00222 (2)0.30630 (2)0.192415 (18)0.03041 (7)
N1−0.10338 (15)0.35066 (13)0.32107 (12)0.0263 (4)
N20.09083 (15)0.23492 (13)0.28111 (12)0.0250 (4)
N3−0.07144 (16)0.22149 (14)0.12033 (13)0.0295 (4)
N40.09239 (14)0.37880 (13)0.05029 (12)0.0244 (3)
C11−0.2061 (2)0.40192 (17)0.34380 (16)0.0332 (5)
H11−0.23240.43190.29080.040*
C12−0.2761 (2)0.41345 (18)0.44094 (18)0.0379 (5)
H12−0.34970.44880.45400.045*
C13−0.2376 (2)0.37322 (18)0.51748 (17)0.0397 (5)
H13−0.28350.38100.58440.048*
C14−0.1315 (2)0.32138 (18)0.49650 (16)0.0351 (5)
H14−0.10240.29380.54850.042*
C15−0.06756 (18)0.31009 (16)0.39809 (15)0.0272 (4)
C160.03963 (19)0.24799 (16)0.37211 (15)0.0280 (4)
H160.07080.21780.42200.034*
C210.19111 (18)0.17015 (16)0.25376 (15)0.0261 (4)
C220.2140 (2)0.13170 (18)0.16535 (16)0.0331 (5)
H220.16640.15200.12490.040*
C230.3057 (2)0.06406 (18)0.13577 (18)0.0366 (5)
H230.32210.03870.07480.044*
C240.37296 (19)0.03402 (17)0.19602 (17)0.0331 (5)
C250.3544 (2)0.07447 (19)0.28212 (17)0.0369 (5)
H250.40340.05500.32160.044*
C260.2645 (2)0.14320 (18)0.31047 (17)0.0341 (5)
H260.25260.17230.36890.041*
C31−0.1550 (2)0.14279 (18)0.15765 (18)0.0386 (5)
H31−0.18200.11620.22740.046*
C32−0.2038 (2)0.0985 (2)0.0986 (2)0.0489 (7)
H32−0.26410.04320.12760.059*
C33−0.1640 (2)0.1356 (2)−0.0027 (2)0.0497 (7)
H33−0.19700.1067−0.04440.060*
C34−0.0754 (2)0.21534 (18)−0.04318 (17)0.0374 (5)
H34−0.04520.2411−0.11320.045*
C35−0.03165 (18)0.25667 (16)0.02032 (15)0.0274 (4)
C360.06125 (18)0.34185 (16)−0.01476 (15)0.0268 (4)
H360.09780.3693−0.08420.032*
C410.18453 (17)0.46002 (15)0.01951 (14)0.0242 (4)
C420.25621 (19)0.46230 (17)0.07779 (16)0.0308 (5)
H420.24330.41010.13490.037*
C430.3465 (2)0.53988 (18)0.05357 (17)0.0347 (5)
H430.39640.54060.09290.042*
C440.36266 (19)0.61608 (17)−0.02864 (17)0.0320 (5)
C450.2927 (2)0.61523 (17)−0.08761 (17)0.0337 (5)
H450.30520.6682−0.14400.040*
C460.20372 (19)0.53644 (16)−0.06401 (15)0.0289 (4)
H460.15600.5347−0.10490.035*
C510.06498 (18)0.24478 (16)0.67108 (15)0.0272 (4)
C52−0.0367 (2)0.17432 (18)0.70596 (15)0.0320 (5)
H52−0.02380.10360.70160.038*
C53−0.1559 (2)0.2044 (2)0.74676 (17)0.0400 (6)
H53−0.22230.15450.76850.048*
C54−0.1784 (2)0.3061 (2)0.75572 (17)0.0421 (6)
H54−0.25960.32670.78290.050*
C55−0.0807 (2)0.37743 (19)0.72457 (17)0.0400 (5)
H55−0.09440.44750.73150.048*
C560.0373 (2)0.34674 (17)0.68315 (16)0.0325 (5)
H560.10280.39740.66190.039*
C610.23163 (19)0.09653 (16)0.60873 (15)0.0286 (4)
C620.3289 (2)0.04312 (17)0.62508 (16)0.0328 (5)
H620.37500.07350.65690.039*
C630.3606 (2)−0.05214 (18)0.59683 (18)0.0407 (6)
H630.4281−0.08480.60840.049*
C640.2946 (2)−0.09949 (18)0.55202 (19)0.0448 (6)
H640.3161−0.16470.53270.054*
C650.1971 (2)−0.05103 (18)0.53558 (18)0.0427 (6)
H650.1504−0.08310.50530.051*
C660.1670 (2)0.04504 (17)0.56331 (16)0.0352 (5)
H660.09960.07710.55090.042*
C710.28089 (18)0.28595 (15)0.51315 (15)0.0264 (4)
C720.2281 (2)0.35601 (16)0.45882 (16)0.0314 (5)
H720.14510.37070.48990.038*
C730.2919 (2)0.40563 (18)0.36052 (17)0.0392 (5)
H730.25180.45230.32620.047*
C740.4128 (2)0.38701 (19)0.31335 (18)0.0437 (6)
H740.45630.42000.24650.052*
C750.4692 (2)0.3197 (2)0.36488 (19)0.0450 (6)
H750.55270.30650.33360.054*
C760.4051 (2)0.27106 (18)0.46188 (17)0.0368 (5)
H760.44670.22550.49560.044*
C810.2680 (2)0.24384 (17)0.70707 (17)0.0323 (5)
C820.2269 (2)0.1840 (2)0.80372 (18)0.0464 (6)
H820.16890.12810.81860.056*
C830.2680 (3)0.2037 (3)0.8778 (2)0.0700 (11)
H830.23810.16130.94210.084*
C840.3510 (4)0.2833 (3)0.8598 (3)0.0828 (13)
H840.37880.29670.91110.099*
C850.3942 (3)0.3443 (3)0.7657 (3)0.0751 (11)
H850.45200.40010.75220.090*
C860.3530 (3)0.3240 (2)0.6902 (2)0.0524 (7)
H860.38420.36630.62580.063*
B0.2094 (2)0.21697 (18)0.62532 (17)0.0264 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.03103 (13)0.04432 (15)0.07066 (19)0.01163 (10)−0.01537 (12)−0.02038 (13)
Br20.04489 (15)0.04317 (15)0.06251 (18)−0.01618 (11)−0.01933 (13)−0.00032 (13)
Cu0.03340 (15)0.03807 (16)0.01943 (13)0.00175 (11)−0.00992 (11)−0.00288 (11)
N10.0289 (9)0.0250 (9)0.0233 (9)−0.0006 (7)−0.0080 (7)−0.0022 (7)
N20.0259 (8)0.0265 (9)0.0228 (9)0.0005 (7)−0.0092 (7)−0.0037 (7)
N30.0306 (9)0.0318 (10)0.0243 (9)−0.0026 (8)−0.0091 (8)−0.0009 (7)
N40.0240 (8)0.0255 (9)0.0226 (9)0.0031 (7)−0.0075 (7)−0.0027 (7)
C110.0364 (12)0.0323 (12)0.0311 (12)0.0058 (9)−0.0130 (10)−0.0035 (9)
C120.0378 (12)0.0357 (13)0.0383 (13)0.0114 (10)−0.0099 (11)−0.0096 (10)
C130.0466 (14)0.0406 (13)0.0293 (12)0.0072 (11)−0.0067 (11)−0.0138 (10)
C140.0422 (13)0.0402 (13)0.0243 (11)0.0055 (10)−0.0121 (10)−0.0090 (10)
C150.0302 (11)0.0273 (11)0.0251 (10)−0.0011 (8)−0.0103 (9)−0.0063 (8)
C160.0303 (11)0.0308 (11)0.0255 (11)0.0027 (9)−0.0134 (9)−0.0048 (9)
C210.0263 (10)0.0259 (10)0.0240 (10)−0.0011 (8)−0.0071 (8)−0.0028 (8)
C220.0349 (12)0.0397 (13)0.0290 (11)0.0059 (10)−0.0154 (10)−0.0088 (10)
C230.0332 (12)0.0420 (13)0.0376 (13)0.0041 (10)−0.0118 (10)−0.0172 (11)
C240.0237 (10)0.0283 (11)0.0441 (13)0.0027 (9)−0.0071 (10)−0.0092 (10)
C250.0307 (12)0.0448 (14)0.0380 (13)0.0055 (10)−0.0165 (10)−0.0058 (11)
C260.0339 (12)0.0408 (13)0.0309 (12)0.0046 (10)−0.0143 (10)−0.0093 (10)
C310.0396 (13)0.0400 (13)0.0322 (12)−0.0071 (10)−0.0117 (10)0.0025 (10)
C320.0487 (15)0.0456 (15)0.0496 (16)−0.0194 (12)−0.0195 (13)0.0046 (12)
C330.0574 (16)0.0521 (16)0.0462 (15)−0.0155 (13)−0.0264 (13)−0.0077 (13)
C340.0454 (13)0.0408 (13)0.0294 (12)−0.0044 (11)−0.0171 (11)−0.0063 (10)
C350.0262 (10)0.0298 (11)0.0256 (11)0.0014 (8)−0.0093 (9)−0.0029 (9)
C360.0261 (10)0.0311 (11)0.0215 (10)0.0036 (8)−0.0075 (8)−0.0021 (8)
C410.0225 (9)0.0257 (10)0.0219 (10)0.0038 (8)−0.0040 (8)−0.0062 (8)
C420.0321 (11)0.0331 (12)0.0256 (11)0.0001 (9)−0.0097 (9)−0.0018 (9)
C430.0335 (12)0.0396 (13)0.0335 (12)−0.0007 (10)−0.0151 (10)−0.0064 (10)
C440.0252 (10)0.0288 (11)0.0378 (13)−0.0027 (9)−0.0055 (9)−0.0071 (10)
C450.0339 (12)0.0307 (12)0.0319 (12)0.0005 (9)−0.0095 (10)0.0021 (9)
C460.0281 (10)0.0331 (11)0.0259 (11)0.0037 (9)−0.0105 (9)−0.0044 (9)
C510.0311 (11)0.0295 (11)0.0219 (10)0.0025 (9)−0.0103 (9)−0.0048 (8)
C520.0357 (12)0.0336 (12)0.0265 (11)−0.0013 (9)−0.0116 (9)−0.0035 (9)
C530.0325 (12)0.0560 (16)0.0278 (12)−0.0060 (11)−0.0088 (10)−0.0011 (11)
C540.0312 (12)0.0616 (17)0.0320 (13)0.0112 (11)−0.0090 (10)−0.0096 (12)
C550.0432 (13)0.0406 (14)0.0339 (13)0.0133 (11)−0.0100 (11)−0.0091 (11)
C560.0336 (11)0.0313 (12)0.0299 (12)0.0023 (9)−0.0077 (9)−0.0062 (9)
C610.0338 (11)0.0226 (10)0.0223 (10)−0.0017 (8)−0.0027 (9)−0.0009 (8)
C620.0323 (11)0.0276 (11)0.0316 (12)−0.0003 (9)−0.0039 (9)−0.0030 (9)
C630.0360 (12)0.0308 (12)0.0450 (14)0.0070 (10)−0.0024 (11)−0.0048 (11)
C640.0508 (15)0.0269 (12)0.0446 (15)0.0014 (11)−0.0005 (12)−0.0098 (11)
C650.0581 (16)0.0299 (12)0.0376 (13)−0.0073 (11)−0.0121 (12)−0.0095 (10)
C660.0447 (13)0.0274 (11)0.0314 (12)0.0002 (10)−0.0116 (10)−0.0035 (9)
C710.0301 (11)0.0227 (10)0.0298 (11)−0.0008 (8)−0.0137 (9)−0.0062 (8)
C720.0379 (12)0.0285 (11)0.0297 (11)0.0038 (9)−0.0130 (10)−0.0082 (9)
C730.0583 (16)0.0289 (12)0.0319 (12)0.0040 (11)−0.0194 (12)−0.0018 (10)
C740.0543 (16)0.0372 (14)0.0307 (13)−0.0051 (12)−0.0073 (12)0.0013 (10)
C750.0336 (12)0.0465 (15)0.0459 (15)−0.0055 (11)−0.0059 (11)−0.0012 (12)
C760.0316 (12)0.0373 (13)0.0390 (13)−0.0011 (10)−0.0128 (10)0.0014 (10)
C810.0370 (12)0.0327 (12)0.0350 (12)0.0163 (9)−0.0189 (10)−0.0142 (10)
C820.0527 (15)0.0594 (17)0.0346 (13)0.0339 (13)−0.0205 (12)−0.0190 (12)
C830.085 (2)0.105 (3)0.0425 (17)0.067 (2)−0.0395 (17)−0.0407 (18)
C840.099 (3)0.117 (3)0.088 (3)0.079 (3)−0.074 (2)−0.079 (3)
C850.079 (2)0.068 (2)0.124 (3)0.0302 (18)−0.072 (2)−0.062 (2)
C860.0624 (17)0.0432 (15)0.074 (2)0.0143 (13)−0.0445 (16)−0.0260 (14)
B0.0315 (12)0.0233 (11)0.0259 (12)0.0030 (9)−0.0121 (10)−0.0046 (9)

Geometric parameters (Å, °)

Br1—C241.896 (2)C45—C461.388 (3)
Br2—C441.897 (2)C45—H450.9500
Cu—N12.0158 (17)C46—H460.9500
Cu—N42.0237 (16)C51—C561.402 (3)
Cu—N32.0278 (17)C51—C521.405 (3)
Cu—N22.0331 (16)C51—B1.648 (3)
N1—C111.339 (3)C52—C531.395 (3)
N1—C151.354 (3)C52—H520.9500
N2—C161.281 (3)C53—C541.379 (4)
N2—C211.425 (3)C53—H530.9500
N3—C311.335 (3)C54—C551.381 (3)
N3—C351.354 (3)C54—H540.9500
N4—C361.285 (2)C55—C561.387 (3)
N4—C411.424 (3)C55—H550.9500
C11—C121.389 (3)C56—H560.9500
C11—H110.9500C61—C621.404 (3)
C12—C131.366 (3)C61—C661.404 (3)
C12—H120.9500C61—B1.646 (3)
C13—C141.376 (3)C62—C631.389 (3)
C13—H130.9500C62—H620.9500
C14—C151.389 (3)C63—C641.379 (4)
C14—H140.9500C63—H630.9500
C15—C161.463 (3)C64—C651.378 (4)
C16—H160.9500C64—H640.9500
C21—C221.391 (3)C65—C661.394 (3)
C21—C261.391 (3)C65—H650.9500
C22—C231.384 (3)C66—H660.9500
C22—H220.9500C71—C721.395 (3)
C23—C241.379 (3)C71—C761.411 (3)
C23—H230.9500C71—B1.652 (3)
C24—C251.382 (3)C72—C731.401 (3)
C25—C261.378 (3)C72—H720.9500
C25—H250.9500C73—C741.379 (3)
C26—H260.9500C73—H730.9500
C31—C321.382 (3)C74—C751.378 (4)
C31—H310.9500C74—H740.9500
C32—C331.375 (4)C75—C761.383 (3)
C32—H320.9500C75—H750.9500
C33—C341.381 (3)C76—H760.9500
C33—H330.9500C81—C861.387 (3)
C34—C351.380 (3)C81—C821.406 (3)
C34—H340.9500C81—B1.647 (3)
C35—C361.463 (3)C82—C831.380 (4)
C36—H360.9500C82—H820.9500
C41—C421.388 (3)C83—C841.362 (5)
C41—C461.390 (3)C83—H830.9500
C42—C431.386 (3)C84—C851.385 (5)
C42—H420.9500C84—H840.9500
C43—C441.381 (3)C85—C861.403 (4)
C43—H430.9500C85—H850.9500
C44—C451.377 (3)C86—H860.9500
N1—Cu—N4135.35 (7)C44—C45—C46119.5 (2)
N1—Cu—N3120.47 (7)C44—C45—H45120.2
N4—Cu—N381.51 (7)C46—C45—H45120.2
N1—Cu—N282.60 (7)C45—C46—C41119.99 (19)
N4—Cu—N2122.20 (7)C45—C46—H46120.0
N3—Cu—N2119.62 (7)C41—C46—H46120.0
C11—N1—C15116.88 (18)C56—C51—C52114.76 (19)
C11—N1—Cu131.53 (14)C56—C51—B118.81 (18)
C15—N1—Cu111.15 (13)C52—C51—B126.31 (19)
C16—N2—C21120.81 (17)C53—C52—C51122.4 (2)
C16—N2—Cu111.51 (14)C53—C52—H52118.8
C21—N2—Cu127.49 (13)C51—C52—H52118.8
C31—N3—C35118.01 (18)C54—C53—C52120.5 (2)
C31—N3—Cu129.64 (15)C54—C53—H53119.7
C35—N3—Cu112.25 (13)C52—C53—H53119.7
C36—N4—C41120.62 (17)C53—C54—C55118.9 (2)
C36—N4—Cu112.89 (14)C53—C54—H54120.5
C41—N4—Cu126.46 (13)C55—C54—H54120.5
N1—C11—C12123.3 (2)C54—C55—C56120.0 (2)
N1—C11—H11118.4C54—C55—H55120.0
C12—C11—H11118.4C56—C55—H55120.0
C13—C12—C11119.0 (2)C55—C56—C51123.4 (2)
C13—C12—H12120.5C55—C56—H56118.3
C11—C12—H12120.5C51—C56—H56118.3
C12—C13—C14119.2 (2)C62—C61—C66114.67 (19)
C12—C13—H13120.4C62—C61—B122.13 (18)
C14—C13—H13120.4C66—C61—B122.54 (19)
C13—C14—C15118.9 (2)C63—C62—C61122.9 (2)
C13—C14—H14120.5C63—C62—H62118.5
C15—C14—H14120.5C61—C62—H62118.5
N1—C15—C14122.72 (19)C64—C63—C62120.3 (2)
N1—C15—C16115.62 (17)C64—C63—H63119.9
C14—C15—C16121.57 (19)C62—C63—H63119.9
N2—C16—C15119.06 (18)C65—C64—C63119.1 (2)
N2—C16—H16120.5C65—C64—H64120.4
C15—C16—H16120.5C63—C64—H64120.4
C22—C21—C26119.3 (2)C64—C65—C66120.0 (2)
C22—C21—N2116.76 (18)C64—C65—H65120.0
C26—C21—N2123.91 (18)C66—C65—H65120.0
C23—C22—C21120.6 (2)C65—C66—C61122.9 (2)
C23—C22—H22119.7C65—C66—H66118.5
C21—C22—H22119.7C61—C66—H66118.5
C24—C23—C22119.0 (2)C72—C71—C76114.5 (2)
C24—C23—H23120.5C72—C71—B125.94 (19)
C22—C23—H23120.5C76—C71—B119.46 (18)
C23—C24—C25121.0 (2)C71—C72—C73122.9 (2)
C23—C24—Br1119.73 (17)C71—C72—H72118.6
C25—C24—Br1119.22 (17)C73—C72—H72118.6
C26—C25—C24119.7 (2)C74—C73—C72120.2 (2)
C26—C25—H25120.1C74—C73—H73119.9
C24—C25—H25120.1C72—C73—H73119.9
C25—C26—C21120.1 (2)C75—C74—C73118.8 (2)
C25—C26—H26119.9C75—C74—H74120.6
C21—C26—H26119.9C73—C74—H74120.6
N3—C31—C32122.5 (2)C74—C75—C76120.4 (2)
N3—C31—H31118.8C74—C75—H75119.8
C32—C31—H31118.8C76—C75—H75119.8
C33—C32—C31119.1 (2)C75—C76—C71123.2 (2)
C33—C32—H32120.5C75—C76—H76118.4
C31—C32—H32120.5C71—C76—H76118.4
C32—C33—C34119.3 (2)C86—C81—C82116.0 (2)
C32—C33—H33120.3C86—C81—B125.4 (2)
C34—C33—H33120.3C82—C81—B118.6 (2)
C35—C34—C33118.5 (2)C83—C82—C81122.3 (3)
C35—C34—H34120.8C83—C82—H82118.9
C33—C34—H34120.8C81—C82—H82118.9
N3—C35—C34122.58 (19)C84—C83—C82120.8 (3)
N3—C35—C36114.60 (17)C84—C83—H83119.6
C34—C35—C36122.83 (19)C82—C83—H83119.6
N4—C36—C35118.61 (18)C83—C84—C85119.0 (3)
N4—C36—H36120.7C83—C84—H84120.5
C35—C36—H36120.7C85—C84—H84120.5
C42—C41—C46119.52 (19)C84—C85—C86120.2 (3)
C42—C41—N4117.29 (18)C84—C85—H85119.9
C46—C41—N4123.18 (17)C86—C85—H85119.9
C43—C42—C41120.7 (2)C81—C86—C85121.7 (3)
C43—C42—H42119.7C81—C86—H86119.2
C41—C42—H42119.7C85—C86—H86119.2
C44—C43—C42118.91 (19)C61—B—C81110.40 (17)
C44—C43—H43120.5C61—B—C51114.88 (17)
C42—C43—H43120.5C81—B—C51104.67 (16)
C45—C44—C43121.4 (2)C61—B—C71104.24 (16)
C45—C44—Br2118.99 (17)C81—B—C71111.07 (17)
C43—C44—Br2119.61 (16)C51—B—C71111.72 (16)
N4—Cu—N1—C1156.5 (2)Cu—N4—C41—C4229.4 (2)
N3—Cu—N1—C11−54.1 (2)C36—N4—C41—C4632.7 (3)
N2—Cu—N1—C11−174.2 (2)Cu—N4—C41—C46−149.60 (16)
N4—Cu—N1—C15−131.45 (13)C46—C41—C42—C430.0 (3)
N3—Cu—N1—C15117.95 (14)N4—C41—C42—C43−178.97 (19)
N2—Cu—N1—C15−2.18 (13)C41—C42—C43—C441.1 (3)
N1—Cu—N2—C161.75 (14)C42—C43—C44—C45−1.2 (3)
N4—Cu—N2—C16141.75 (14)C42—C43—C44—Br2176.76 (17)
N3—Cu—N2—C16−119.20 (14)C43—C44—C45—C460.2 (3)
N1—Cu—N2—C21176.71 (17)Br2—C44—C45—C46−177.81 (16)
N4—Cu—N2—C21−43.30 (18)C44—C45—C46—C411.0 (3)
N3—Cu—N2—C2155.75 (18)C42—C41—C46—C45−1.1 (3)
N1—Cu—N3—C31−41.1 (2)N4—C41—C46—C45177.86 (19)
N4—Cu—N3—C31−179.4 (2)C56—C51—C52—C531.7 (3)
N2—Cu—N3—C3158.3 (2)B—C51—C52—C53177.76 (19)
N1—Cu—N3—C35135.06 (14)C51—C52—C53—C54−1.0 (3)
N4—Cu—N3—C35−3.25 (14)C52—C53—C54—C55−0.6 (3)
N2—Cu—N3—C35−125.58 (14)C53—C54—C55—C561.3 (3)
N1—Cu—N4—C36−123.84 (14)C54—C55—C56—C51−0.5 (3)
N3—Cu—N4—C361.50 (14)C52—C51—C56—C55−1.0 (3)
N2—Cu—N4—C36121.28 (14)B—C51—C56—C55−177.4 (2)
N1—Cu—N4—C4158.28 (18)C66—C61—C62—C631.3 (3)
N3—Cu—N4—C41−176.38 (16)B—C61—C62—C63−169.6 (2)
N2—Cu—N4—C41−56.60 (17)C61—C62—C63—C64−1.1 (4)
C15—N1—C11—C12−0.9 (3)C62—C63—C64—C650.1 (4)
Cu—N1—C11—C12170.75 (17)C63—C64—C65—C660.6 (4)
N1—C11—C12—C131.8 (4)C64—C65—C66—C61−0.3 (4)
C11—C12—C13—C14−0.8 (4)C62—C61—C66—C65−0.6 (3)
C12—C13—C14—C15−1.0 (4)B—C61—C66—C65170.3 (2)
C11—N1—C15—C14−1.0 (3)C76—C71—C72—C731.6 (3)
Cu—N1—C15—C14−174.33 (17)B—C71—C72—C73−174.54 (19)
C11—N1—C15—C16175.56 (18)C71—C72—C73—C74−0.6 (3)
Cu—N1—C15—C162.3 (2)C72—C73—C74—C75−0.5 (4)
C13—C14—C15—N12.0 (3)C73—C74—C75—C760.6 (4)
C13—C14—C15—C16−174.4 (2)C74—C75—C76—C710.5 (4)
C21—N2—C16—C15−176.37 (17)C72—C71—C76—C75−1.5 (3)
Cu—N2—C16—C15−1.0 (2)B—C71—C76—C75174.9 (2)
N1—C15—C16—N2−0.9 (3)C86—C81—C82—C830.2 (3)
C14—C15—C16—N2175.8 (2)B—C81—C82—C83−177.6 (2)
C16—N2—C21—C22158.5 (2)C81—C82—C83—C840.2 (4)
Cu—N2—C21—C22−16.1 (3)C82—C83—C84—C85−0.2 (4)
C16—N2—C21—C26−20.7 (3)C83—C84—C85—C86−0.1 (4)
Cu—N2—C21—C26164.72 (16)C82—C81—C86—C85−0.6 (3)
C26—C21—C22—C232.5 (3)B—C81—C86—C85177.1 (2)
N2—C21—C22—C23−176.7 (2)C84—C85—C86—C810.6 (4)
C21—C22—C23—C241.0 (3)C62—C61—B—C81−25.8 (3)
C22—C23—C24—C25−3.4 (4)C66—C61—B—C81163.98 (19)
C22—C23—C24—Br1176.13 (17)C62—C61—B—C51−143.88 (19)
C23—C24—C25—C262.3 (4)C66—C61—B—C5145.9 (3)
Br1—C24—C25—C26−177.25 (17)C62—C61—B—C7193.5 (2)
C24—C25—C26—C211.3 (3)C66—C61—B—C71−76.7 (2)
C22—C21—C26—C25−3.7 (3)C86—C81—B—C61124.4 (2)
N2—C21—C26—C25175.5 (2)C82—C81—B—C61−58.0 (2)
C35—N3—C31—C32−1.7 (3)C86—C81—B—C51−111.4 (2)
Cu—N3—C31—C32174.20 (19)C82—C81—B—C5166.2 (2)
N3—C31—C32—C330.9 (4)C86—C81—B—C719.3 (3)
C31—C32—C33—C340.7 (4)C82—C81—B—C71−173.12 (18)
C32—C33—C34—C35−1.4 (4)C56—C51—B—C61−176.98 (18)
C31—N3—C35—C340.9 (3)C52—C51—B—C617.1 (3)
Cu—N3—C35—C34−175.68 (17)C56—C51—B—C8161.8 (2)
C31—N3—C35—C36−179.05 (19)C52—C51—B—C81−114.1 (2)
Cu—N3—C35—C364.3 (2)C56—C51—B—C71−58.5 (2)
C33—C34—C35—N30.6 (3)C52—C51—B—C71125.6 (2)
C33—C34—C35—C36−179.4 (2)C72—C71—B—C61121.5 (2)
C41—N4—C36—C35178.46 (17)C76—C71—B—C61−54.4 (2)
Cu—N4—C36—C350.4 (2)C72—C71—B—C81−119.6 (2)
N3—C35—C36—N4−3.3 (3)C76—C71—B—C8164.5 (2)
C34—C35—C36—N4176.7 (2)C72—C71—B—C51−3.1 (3)
C36—N4—C41—C42−148.37 (19)C76—C71—B—C51−179.04 (18)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2107).

References

  • Armaroli, N. (2001). Chem. Soc. Rev.30, 113–117.
  • Beurskens, P. T., Beurskens, G., de Gelder, R., García-Granda, S., Israel, R., Gould, R. O. & Smits, J. M. M. (1999). The DIRDIF99 Program System. Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands.
  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Dehghanpour, S., Bouslimani, N., Welter, R. & Mojahed, F. (2007). Polyhedron, 26, 154–162.
  • Dehghanpour, S. & Mahmoudi, A. (2007). Main Group. Chem.6, 121–130.
  • Sakaki, S., Kuroki, T. & Hamada, T. (2002). J. Chem. Soc. Dalton Trans. pp. 840–842.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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