Bis(diphenyl-p-tolyl­phosphane-κP)(2-hy­droxy-3,5,7-bromo­cyclo­hepta-2,4,6-trienonato-κ2O,O′)copper(I)

Barnard, N.I.; Hill, T.N.

doi:10.1107/S1600536812042286

Bis(diphenyl-p-tolylphosphane-κP)(2-hydroxy-3,5,7-bromocyclohepta-2,4,6-trienonato-κ²O,O′)copper(I)

The Cu^I atom in the title compund, [Cu(C₇H₂Br₃O₂)(C₁₉H₁₇P)₂], is located on a twofold rotation axis; the 3,5,7-tribromotropolonate anion coordinates as a bidentate ligand with a bite angle of 76.42 (9)°. An intramolecular C—H

O interaction occurs. Within the crystal, extensive weak C—H

π interactions contribute to the herringbone pattern observed in the packing of the molecules.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536812042286/ng5299sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536812042286/ng5299Isup2.hkl Contains datablock I

CCDC reference: 909723

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.006 Å
R factor = 0.044
wR factor = 0.130
Data-to-parameter ratio = 20.8

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    Br2    --  C5      ..        8.0 su

Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C5

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large.      16.66
PLAT380_ALERT_4_G Check Incorrectly? Oriented X(sp2)-Methyl Moiety       C137
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         28
PLAT960_ALERT_3_G Number of Intensities with I .LT. - 2*sig(I) ...          2

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

Tropolone and its derivatives have been of interest ever since their first discovery in the early 1940's (Dewar, 1945); they are known to have applications in both pharmacology (Hill & Steyl, 2008) and catalysis (Crous et al., 2005). Bis troplolonato copper(II) complexes are most frequently reported (Ho, 2010; Ho et al., 2009; Chipperfield et al., 1998; Hasegawa et al., 1997). Recently, reseach in this area has been extended to include copper(I) phosphine metal complexes and the effect the troplonato ligand has on the solid state and chemical behaviour of these complexes (Steyl, 2007; Steyl & Roodt, 2006; Roodt et al., 2003). In this paper, the structure of the tropolonato-bis[diphenyl(p-tolyl)-phosphine]copper(I) complex is reported (Fig. 1).

The Cu—O and Cu—P bond distances were found to be 2.090 (1) Å and 2.229 (1) Å respectively and are well within comparable ranges for copper(I) phosphine complexes. the bond angles about the Cu atom show significantly distorted tetrahedral coordination (Table 1). The bidentate bite angle O2—Cu—O2ⁱ observed at 76.42 (9)° is close to analogous angles in previously reported structures (Steyl, 2009).

The title compound (I) displays intramolecular C—H···Br interactions with a distance of 3.4666 (5) Å as seen in Figure 2. Figure 3 illustrates the packing diagram for compound (I), a zigzag pattern is adopted with inverted repeating units creating diagonals in all directions. This intricate design is achieved though numerous C—H···π itermolecular interactions see Figure 4. These interactions occur between methyl H atoms of the p-tolyl and phenyl π, phenyl H to p-tolyl π, phenyl H to phenyl π and p-tolyl π to p-tolyl The C—H···π itermolecular interactions range from 3.1816 (1) Å - 3.7267 (2) Å.

Related literature top

For background to tropolone and its derivatives, see: Dewar (1945); Hill & Steyl (2008); Crous et al. (2005). For bis-troplolonato–copper(II) complexes, see: Chipperfield et al. (1998); Hasegawa et al. (1997); Ho (2010); Ho et al. (2009). For work on the effect the troplonato ligand has on the solid state and chemical behaviour of copper(I) phosphine metal complexes, see: Roodt et al. (2003); Steyl (2007, 2009); Steyl & Hill (2009); Steyl & Roodt (2006).

Experimental top

3,5,7-Tribomotropolone (0.3 mmol) was dissolved in methanol (20 ml). To this solution was added Bis(diphenyl(p-tolyl)-phosphine) copper nitrate (0.3 mmol). The resulting mixture was stirred at room temperature for 30 minutes before filtering. The filtrate was then slowly evaporated yielding crystals siutable for X-ray diffraction after 48 h.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. A view of (I). Displacement ellipsoids are drawn at 50% proabiity level. Hydrogen atoms have been ommited.
	Fig. 2. Intramolecular H···Br interactions (dashed bonds) for the title compound.
	Fig. 3. A packing diagram of the title compound, illustrating the herringbone patturnation as viewed along the [1,0,1] axis. Hydrogen atoms have been ommited.
	Fig. 4. Four differing views highlighting elaborate web of H···π intermolecular interactions (dashed bonds) creating the three dimentional herringbone design, non-relevant hydrogen atoms have been ommited for clarity.

Bis(diphenyl-p-tolylphosphane-κP)(2-hydroxy-3,5,7-bromocyclohepta-2,4,6-trienonato-κ²O,O')copper(I) top

Crystal data top

[Cu(C₇H₂Br₃O₂)(C₁₉H₁₇P)₂]	F(000) = 1944
M_r = 973.95	D_x = 1.604 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8436 reflections
a = 15.4522 (8) Å	θ = 2.3–28.4°
b = 13.9073 (8) Å	µ = 3.63 mm⁻¹
c = 19.3269 (10) Å	T = 100 K
β = 103.862 (3)°	Cuboid, green
V = 4032.4 (4) Å³	0.18 × 0.09 × 0.06 mm
Z = 4

Data collection top

Bruker X8 APEXII 4K Kappa CCD diffractometer	5022 independent reflections
Radiation source: sealed tube	3970 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
Detector resolution: 512 pixels mm^-1	θ_max = 28.4°, θ_min = 2°
ϕ and ω scans	h = −19→20
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −15→18
T_min = 0.686, T_max = 0.746	l = −25→25
27602 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0661P)² + 16.6643P] where P = (F_o² + 2F_c²)/3
5022 reflections	(Δ/σ)_max < 0.001
241 parameters	Δρ_max = 1.51 e Å⁻³
0 restraints	Δρ_min = −1.57 e Å⁻³

Crystal data top

[Cu(C₇H₂Br₃O₂)(C₁₉H₁₇P)₂]	V = 4032.4 (4) Å³
M_r = 973.95	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 15.4522 (8) Å	µ = 3.63 mm⁻¹
b = 13.9073 (8) Å	T = 100 K
c = 19.3269 (10) Å	0.18 × 0.09 × 0.06 mm
β = 103.862 (3)°

Data collection top

Bruker X8 APEXII 4K Kappa CCD diffractometer	5022 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	3970 reflections with I > 2σ(I)
T_min = 0.686, T_max = 0.746	R_int = 0.053
27602 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0661P)² + 16.6643P] where P = (F_o² + 2F_c²)/3
5022 reflections	Δρ_max = 1.51 e Å⁻³
241 parameters	Δρ_min = −1.57 e Å⁻³

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C2	0.5382 (2)	0.6353 (3)	0.28258 (18)	0.0213 (7)
C3	0.5717 (2)	0.7199 (3)	0.32159 (19)	0.0230 (7)
C4	0.5556 (2)	0.8171 (3)	0.3086 (2)	0.0294 (8)
H4	0.5867	0.8596	0.3446	0.035*
C5	0.5	0.8599 (3)	0.25	0.0295 (12)
C111	0.3102 (2)	0.3211 (3)	0.25441 (19)	0.0242 (7)
C112	0.2526 (2)	0.3880 (3)	0.2148 (2)	0.0309 (8)
H112	0.2662	0.4546	0.2202	0.037*
C113	0.1744 (3)	0.3578 (4)	0.1667 (2)	0.0373 (10)
H113	0.1339	0.4041	0.1411	0.045*
C114	0.1562 (3)	0.2615 (4)	0.1565 (2)	0.0375 (10)
H114	0.1041	0.2411	0.1227	0.045*
C115	0.2132 (3)	0.1946 (3)	0.1954 (2)	0.0384 (10)
H115	0.2003	0.128	0.1883	0.046*
C116	0.2898 (2)	0.2235 (3)	0.2451 (2)	0.0310 (8)
H116	0.3281	0.1769	0.2725	0.037*
C121	0.4606 (2)	0.2639 (2)	0.36831 (19)	0.0221 (7)
C122	0.5385 (3)	0.2234 (3)	0.3588 (2)	0.0317 (8)
H122	0.5645	0.2472	0.3223	0.038*
C123	0.5799 (3)	0.1478 (3)	0.4021 (3)	0.0432 (11)
H123	0.6334	0.1205	0.3949	0.052*
C124	0.5423 (3)	0.1126 (3)	0.4559 (2)	0.0412 (10)
H124	0.57	0.0613	0.4856	0.049*
C125	0.4650 (3)	0.1526 (3)	0.4655 (3)	0.0470 (12)
H125	0.4394	0.1292	0.5023	0.056*
C126	0.4237 (3)	0.2272 (3)	0.4219 (3)	0.0391 (10)
H126	0.3697	0.2535	0.4288	0.047*
C131	0.3738 (2)	0.4421 (2)	0.37497 (17)	0.0202 (7)
C132	0.2920 (2)	0.4256 (3)	0.39248 (19)	0.0236 (7)
H132	0.2525	0.3778	0.3677	0.028*
C133	0.2690 (2)	0.4791 (3)	0.4460 (2)	0.0277 (8)
H133	0.2138	0.4667	0.4579	0.033*
C134	0.3244 (3)	0.5498 (3)	0.4823 (2)	0.0303 (8)
C135	0.4049 (2)	0.5684 (3)	0.46311 (19)	0.0263 (7)
H135	0.443	0.6183	0.4864	0.032*
C136	0.4292 (2)	0.5143 (3)	0.41023 (18)	0.0222 (7)
H136	0.4841	0.527	0.3981	0.027*
C137	0.3016 (3)	0.6032 (4)	0.5422 (3)	0.0512 (13)
H13A	0.3485	0.6502	0.5612	0.077*
H13B	0.2964	0.5579	0.5798	0.077*
H13C	0.2447	0.6368	0.5249	0.077*
O2	0.56859 (15)	0.55420 (17)	0.30362 (13)	0.0227 (5)
P1	0.41329 (5)	0.36611 (6)	0.31230 (5)	0.01920 (18)
Cu1	0.5	0.43613 (4)	0.25	0.01987 (15)
Br1	0.65536 (3)	0.69166 (3)	0.40942 (2)	0.03295 (13)
Br2	0.5	0.99600 (5)	0.25	0.0638 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0140 (14)	0.0293 (18)	0.0231 (17)	−0.0008 (13)	0.0096 (13)	0.0021 (14)
C3	0.0171 (14)	0.0279 (18)	0.0259 (17)	−0.0019 (13)	0.0090 (13)	−0.0002 (14)
C4	0.0225 (17)	0.0277 (19)	0.041 (2)	−0.0066 (14)	0.0132 (15)	−0.0078 (16)
C5	0.027 (2)	0.011 (2)	0.054 (3)	0	0.016 (2)	0
C111	0.0150 (14)	0.036 (2)	0.0230 (17)	−0.0030 (14)	0.0071 (12)	−0.0048 (15)
C112	0.0273 (18)	0.037 (2)	0.0276 (19)	−0.0005 (16)	0.0047 (15)	−0.0003 (16)
C113	0.0256 (19)	0.061 (3)	0.0243 (19)	0.0036 (18)	0.0034 (15)	0.0005 (18)
C114	0.0222 (17)	0.062 (3)	0.030 (2)	−0.0106 (18)	0.0086 (15)	−0.015 (2)
C115	0.030 (2)	0.047 (3)	0.041 (2)	−0.0167 (18)	0.0150 (18)	−0.017 (2)
C116	0.0234 (17)	0.036 (2)	0.036 (2)	−0.0069 (15)	0.0102 (15)	−0.0061 (17)
C121	0.0212 (15)	0.0196 (17)	0.0260 (17)	0.0014 (13)	0.0070 (13)	−0.0005 (13)
C122	0.0262 (18)	0.036 (2)	0.036 (2)	0.0055 (16)	0.0138 (16)	0.0070 (17)
C123	0.034 (2)	0.044 (3)	0.055 (3)	0.0189 (19)	0.018 (2)	0.018 (2)
C124	0.045 (2)	0.034 (2)	0.047 (2)	0.0110 (19)	0.015 (2)	0.0116 (19)
C125	0.054 (3)	0.040 (2)	0.057 (3)	0.013 (2)	0.034 (2)	0.021 (2)
C126	0.035 (2)	0.036 (2)	0.055 (3)	0.0110 (17)	0.027 (2)	0.015 (2)
C131	0.0173 (14)	0.0229 (17)	0.0209 (16)	0.0055 (13)	0.0057 (12)	0.0038 (13)
C132	0.0178 (15)	0.0269 (17)	0.0273 (18)	0.0018 (13)	0.0076 (13)	0.0003 (14)
C133	0.0203 (16)	0.037 (2)	0.0273 (18)	0.0075 (15)	0.0077 (14)	0.0022 (15)
C134	0.0307 (18)	0.036 (2)	0.0238 (18)	0.0155 (16)	0.0051 (14)	−0.0003 (16)
C135	0.0262 (17)	0.0257 (18)	0.0227 (17)	0.0044 (14)	−0.0026 (13)	0.0007 (14)
C136	0.0176 (14)	0.0236 (17)	0.0239 (17)	0.0037 (13)	0.0021 (12)	0.0024 (13)
C137	0.045 (3)	0.070 (3)	0.039 (2)	0.012 (2)	0.010 (2)	−0.018 (2)
O2	0.0171 (11)	0.0233 (13)	0.0272 (12)	−0.0008 (9)	0.0041 (9)	0.0014 (10)
P1	0.0145 (4)	0.0208 (4)	0.0234 (4)	−0.0004 (3)	0.0068 (3)	−0.0008 (3)
Cu1	0.0149 (3)	0.0214 (3)	0.0249 (3)	0	0.0078 (2)	0
Br1	0.0317 (2)	0.0367 (2)	0.0276 (2)	−0.00878 (16)	0.00144 (15)	−0.00242 (16)
Br2	0.0539 (4)	0.0268 (3)	0.1064 (7)	0	0.0112 (4)	0

Geometric parameters (Å, º) top

C2—O2	1.252 (4)	C123—C124	1.396 (6)
C2—C3	1.426 (5)	C123—H123	0.95
C2—C2ⁱ	1.506 (6)	C124—C125	1.370 (6)
C3—C4	1.387 (5)	C124—H124	0.95
C3—Br1	1.911 (4)	C125—C126	1.391 (6)
C4—C5	1.382 (5)	C125—H125	0.95
C4—H4	0.95	C126—H126	0.95
C5—C4ⁱ	1.382 (5)	C131—C136	1.388 (5)
C5—Br2	1.893 (5)	C131—C132	1.403 (4)
C111—C112	1.384 (5)	C131—P1	1.820 (3)
C111—C116	1.395 (5)	C132—C133	1.387 (5)
C111—P1	1.824 (3)	C132—H132	0.95
C112—C113	1.400 (5)	C133—C134	1.381 (6)
C112—H112	0.95	C133—H133	0.95
C113—C114	1.375 (7)	C134—C135	1.405 (5)
C113—H113	0.95	C134—C137	1.486 (6)
C114—C115	1.374 (7)	C135—C136	1.391 (5)
C114—H114	0.95	C135—H135	0.95
C115—C116	1.392 (6)	C136—H136	0.95
C115—H115	0.95	C137—H13A	0.98
C116—H116	0.95	C137—H13B	0.98
C121—C122	1.381 (5)	C137—H13C	0.98
C121—C126	1.393 (5)	O2—Cu1	2.090 (2)
C121—P1	1.830 (4)	P1—Cu1	2.2284 (9)
C122—C123	1.398 (6)	Cu1—O2ⁱ	2.090 (2)
C122—H122	0.95	Cu1—P1ⁱ	2.2284 (9)

O2—C2—C3	120.7 (3)	C124—C125—H125	119.7
O2—C2—C2ⁱ	115.45 (19)	C126—C125—H125	119.7
C3—C2—C2ⁱ	123.7 (2)	C125—C126—C121	120.9 (4)
C4—C3—C2	133.0 (3)	C125—C126—H126	119.5
C4—C3—Br1	114.5 (3)	C121—C126—H126	119.5
C2—C3—Br1	112.5 (3)	C136—C131—C132	119.0 (3)
C5—C4—C3	128.1 (4)	C136—C131—P1	118.8 (2)
C5—C4—H4	115.9	C132—C131—P1	122.0 (3)
C3—C4—H4	115.9	C133—C132—C131	119.9 (3)
C4ⁱ—C5—C4	129.0 (5)	C133—C132—H132	120.1
C4ⁱ—C5—Br2	115.5 (2)	C131—C132—H132	120.1
C4—C5—Br2	115.5 (2)	C134—C133—C132	121.5 (3)
C112—C111—C116	119.1 (3)	C134—C133—H133	119.2
C112—C111—P1	117.4 (3)	C132—C133—H133	119.2
C116—C111—P1	123.4 (3)	C133—C134—C135	118.5 (3)
C111—C112—C113	120.2 (4)	C133—C134—C137	121.2 (4)
C111—C112—H112	119.9	C135—C134—C137	120.3 (4)
C113—C112—H112	119.9	C136—C135—C134	120.4 (3)
C114—C113—C112	120.2 (4)	C136—C135—H135	119.8
C114—C113—H113	119.9	C134—C135—H135	119.8
C112—C113—H113	119.9	C131—C136—C135	120.6 (3)
C113—C114—C115	119.9 (4)	C131—C136—H136	119.7
C113—C114—H114	120.1	C135—C136—H136	119.7
C115—C114—H114	120.1	C134—C137—H13A	109.5
C114—C115—C116	120.6 (4)	C134—C137—H13B	109.5
C114—C115—H115	119.7	H13A—C137—H13B	109.5
C116—C115—H115	119.7	C134—C137—H13C	109.5
C115—C116—C111	119.9 (4)	H13A—C137—H13C	109.5
C115—C116—H116	120.1	H13B—C137—H13C	109.5
C111—C116—H116	120.1	C2—O2—Cu1	116.1 (2)
C122—C121—C126	118.3 (3)	C131—P1—C111	102.98 (15)
C122—C121—P1	118.4 (3)	C131—P1—C121	101.98 (16)
C126—C121—P1	123.2 (3)	C111—P1—C121	105.21 (17)
C121—C122—C123	121.0 (4)	C131—P1—Cu1	116.55 (12)
C121—C122—H122	119.5	C111—P1—Cu1	111.62 (12)
C123—C122—H122	119.5	C121—P1—Cu1	116.91 (11)
C122—C123—C124	119.9 (4)	O2—Cu1—O2ⁱ	76.42 (13)
C122—C123—H123	120.1	O2—Cu1—P1	112.00 (7)
C124—C123—H123	120.1	O2ⁱ—Cu1—P1	108.19 (7)
C125—C124—C123	119.3 (4)	O2—Cu1—P1ⁱ	108.19 (7)
C125—C124—H124	120.3	O2ⁱ—Cu1—P1ⁱ	112.00 (7)
C123—C124—H124	120.3	P1—Cu1—P1ⁱ	128.18 (5)
C124—C125—C126	120.6 (4)

O2—C2—C3—C4	174.7 (4)	C134—C135—C136—C131	0.9 (5)
C2ⁱ—C2—C3—C4	−9.2 (7)	C3—C2—O2—Cu1	171.0 (2)
O2—C2—C3—Br1	−5.6 (4)	C2ⁱ—C2—O2—Cu1	−5.4 (4)
C2ⁱ—C2—C3—Br1	170.5 (3)	C136—C131—P1—C111	−157.1 (3)
C2—C3—C4—C5	−1.1 (6)	C132—C131—P1—C111	27.6 (3)
Br1—C3—C4—C5	179.2 (2)	C136—C131—P1—C121	94.0 (3)
C3—C4—C5—C4ⁱ	2.7 (3)	C132—C131—P1—C121	−81.3 (3)
C3—C4—C5—Br2	−177.3 (3)	C136—C131—P1—Cu1	−34.5 (3)
C116—C111—C112—C113	0.9 (5)	C132—C131—P1—Cu1	150.1 (2)
P1—C111—C112—C113	176.9 (3)	C112—C111—P1—C131	62.6 (3)
C111—C112—C113—C114	−2.6 (6)	C116—C111—P1—C131	−121.6 (3)
C112—C113—C114—C115	2.2 (6)	C112—C111—P1—C121	169.0 (3)
C113—C114—C115—C116	−0.1 (6)	C116—C111—P1—C121	−15.1 (3)
C114—C115—C116—C111	−1.6 (6)	C112—C111—P1—Cu1	−63.2 (3)
C112—C111—C116—C115	1.2 (5)	C116—C111—P1—Cu1	112.6 (3)
P1—C111—C116—C115	−174.6 (3)	C122—C121—P1—C131	−141.0 (3)
C126—C121—C122—C123	−0.4 (6)	C126—C121—P1—C131	36.4 (4)
P1—C121—C122—C123	177.2 (4)	C122—C121—P1—C111	111.8 (3)
C121—C122—C123—C124	−0.2 (7)	C126—C121—P1—C111	−70.8 (4)
C122—C123—C124—C125	0.1 (8)	C122—C121—P1—Cu1	−12.7 (3)
C123—C124—C125—C126	0.4 (8)	C126—C121—P1—Cu1	164.8 (3)
C124—C125—C126—C121	−1.0 (8)	C2—O2—Cu1—O2ⁱ	2.14 (18)
C122—C121—C126—C125	0.9 (7)	C2—O2—Cu1—P1	−102.3 (2)
P1—C121—C126—C125	−176.5 (4)	C2—O2—Cu1—P1ⁱ	111.2 (2)
C136—C131—C132—C133	−2.1 (5)	C131—P1—Cu1—O2	26.45 (14)
P1—C131—C132—C133	173.3 (3)	C111—P1—Cu1—O2	144.35 (15)
C131—C132—C133—C134	0.8 (6)	C121—P1—Cu1—O2	−94.47 (15)
C132—C133—C134—C135	1.3 (6)	C131—P1—Cu1—O2ⁱ	−55.86 (14)
C132—C133—C134—C137	−176.7 (4)	C111—P1—Cu1—O2ⁱ	62.04 (15)
C133—C134—C135—C136	−2.1 (5)	C121—P1—Cu1—O2ⁱ	−176.78 (14)
C137—C134—C135—C136	175.8 (4)	C131—P1—Cu1—P1ⁱ	164.68 (12)
C132—C131—C136—C135	1.2 (5)	C111—P1—Cu1—P1ⁱ	−77.41 (13)
P1—C131—C136—C135	−174.3 (3)	C121—P1—Cu1—P1ⁱ	43.76 (13)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C121–C126 and C131–C136 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C136—H136···O2	0.95	2.52	3.365 (4)	149
C115—H115···Cg3ⁱⁱ	0.95	2.86	3.621 (4)	138
C137—H13A···Cg2ⁱⁱⁱ	0.98	3.18	4.144 (6)	168

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

Experimental details

Crystal data
Chemical formula	[Cu(C₇H₂Br₃O₂)(C₁₉H₁₇P)₂]
M_r	973.95
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	15.4522 (8), 13.9073 (8), 19.3269 (10)
β (°)	103.862 (3)
V (Å³)	4032.4 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.63
Crystal size (mm)	0.18 × 0.09 × 0.06

Data collection
Diffractometer	Bruker X8 APEXII 4K Kappa CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.686, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	27602, 5022, 3970
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.130, 1.04
No. of reflections	5022
No. of parameters	241
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0661P)² + 16.6643P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.51, −1.57

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005), WinGX (Farrugia, 1999).