Chloro­bis[diphen­yl(p-tol­yl)phosphine]copper(I)

The title compound, [CuCl(C₁₉H₁₇P)₂], is an example of an asymmetric bis­phosphine complex of copper(I). It crystallizes with a distorted trigonal-planar geometry about the copper(I) metal centre. The diphen­yl(p-tol­yl)phosphine groups adopt an eclipsed configuration in the solid state. The most important bond distances and angles include Cu-Cl = 2.2330 (12) Å, Cu-P = 2.2570 (13) Å, Cu-P (trans to Cl) = 2.2579 (12) Å and P-Cu-P = 126.72 (5)°.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.062
• wR factor = 0.150
• Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.74 Ratio
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Putz, 2004); software used to prepare material for publication: SHELXL97.

Chlorobis[diphenyl(p-tolyl)phosphine]copper(I)

Crystal data

[CuCl(C19H17P)2]	F(000) = 1352
Mr = 651.58	Dx = 1.368 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2575 reflections
a = 11.5427 (7) Å	θ = 2.3–22.1°
b = 18.1087 (12) Å	µ = 0.90 mm^−1
c = 15.4940 (9) Å	T = 100 K
β = 102.266 (3)°	Cuboid, white
V = 3164.7 (3) Å^3	0.14 × 0.12 × 0.06 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	6891 independent reflections
Radiation source: fine-focus sealed tube	4276 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.076
Detector resolution: 512 pixels mm^-1	θmax = 27.0°, θmin = 2.3°
φ and ω scans	h = −14→13
Absorption correction: multi-scan (SADABS; Bruker, 1998)	k = −22→23
Tmin = 0.884, Tmax = 0.948	l = −19→19
24407 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.150	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0434P)^2 + 6.7108P] where P = (Fo^2 + 2Fc^2)/3
6891 reflections	(Δ/σ)max = 0.001
379 parameters	Δρmax = 0.75 e Å^−3
0 restraints	Δρmin = −0.49 e Å^−3

Special details

Experimental. Spectral data: ¹H NMR (CD₃CN, 300 MHz): 7.13 (m, 4H), 7.25 (m, 24H), 2.12 (s, 3H); ¹H NMR (CD₃CN, 121.5 MHz) 4.33 (broad m).

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu	0.82237 (5)	0.19671 (3)	0.57776 (4)	0.02919 (17)
P2	1.00073 (10)	0.24852 (6)	0.63264 (8)	0.0256 (3)
Cl	0.81616 (10)	0.07653 (6)	0.54482 (9)	0.0396 (3)
P1	0.64564 (10)	0.25504 (6)	0.54546 (9)	0.0336 (3)
C41	1.1256 (4)	0.1862 (2)	0.6666 (3)	0.0283 (10)
C42	1.2273 (4)	0.2058 (3)	0.7287 (3)	0.0336 (11)
H42	1.2306	0.2520	0.7581	0.040*
C46	1.1217 (4)	0.1174 (2)	0.6261 (3)	0.0337 (11)
H46	1.0524	0.1025	0.5850	0.040*
C43	1.3236 (4)	0.1584 (3)	0.7479 (3)	0.0361 (11)
H43	1.3928	0.1726	0.7896	0.043*
C45	1.2190 (4)	0.0704 (3)	0.6458 (3)	0.0387 (12)
H45	1.2166	0.0239	0.6171	0.046*
C44	1.3195 (4)	0.0912 (3)	0.7071 (3)	0.0386 (12)
H44	1.3855	0.0588	0.7208	0.046*
C51	1.0053 (4)	0.3062 (2)	0.7297 (3)	0.0271 (9)
C52	1.0398 (4)	0.3802 (2)	0.7333 (3)	0.0311 (10)
H52	1.0679	0.4012	0.6854	0.037*
C56	0.9667 (4)	0.2763 (3)	0.8017 (3)	0.0348 (11)
H56	0.9442	0.2258	0.8009	0.042*
C54	0.9930 (4)	0.3933 (3)	0.8760 (3)	0.0387 (12)
H54	0.9871	0.4230	0.9254	0.046*
C53	1.0335 (4)	0.4236 (3)	0.8059 (3)	0.0360 (11)
H53	1.0569	0.4739	0.8076	0.043*
C55	0.9610 (4)	0.3194 (3)	0.8739 (3)	0.0412 (13)
H55	0.9350	0.2983	0.9227	0.049*
C26	0.5020 (4)	0.3010 (3)	0.6632 (3)	0.0411 (12)
H26	0.4409	0.2706	0.6309	0.049*
C21	0.6099 (4)	0.3068 (2)	0.6369 (3)	0.0344 (11)
C22	0.6960 (4)	0.3514 (3)	0.6875 (4)	0.0559 (17)
H22	0.7710	0.3554	0.6719	0.067*
C25	0.4839 (5)	0.3393 (3)	0.7359 (4)	0.0477 (14)
H25	0.4099	0.3349	0.7531	0.057*
C23	0.6768 (5)	0.3899 (3)	0.7589 (4)	0.0622 (18)
H23	0.7373	0.4209	0.7910	0.075*
C24	0.5712 (5)	0.3839 (3)	0.7844 (4)	0.0463 (13)
H24	0.5578	0.4100	0.8345	0.056*
C11	0.5146 (4)	0.1982 (2)	0.5064 (3)	0.0322 (10)
C12	0.5177 (4)	0.1243 (3)	0.5309 (4)	0.0470 (14)
H12	0.5887	0.1035	0.5644	0.056*
C15	0.3106 (4)	0.1821 (3)	0.4333 (3)	0.0415 (12)
H15	0.2391	0.2023	0.3997	0.050*
C16	0.4102 (4)	0.2266 (3)	0.4570 (3)	0.0358 (11)
H16	0.4066	0.2769	0.4392	0.043*
C13	0.4177 (4)	0.0810 (3)	0.5064 (4)	0.0551 (16)
H13	0.4207	0.0305	0.5236	0.066*
C14	0.3146 (4)	0.1093 (3)	0.4579 (4)	0.0421 (13)
H14	0.2464	0.0789	0.4414	0.051*
C31	0.6411 (4)	0.3225 (2)	0.4585 (3)	0.0342 (11)
C32	0.6751 (4)	0.3006 (3)	0.3815 (4)	0.0419 (12)
H32	0.6931	0.2501	0.3745	0.050*
C33	0.6837 (4)	0.3499 (3)	0.3143 (4)	0.0416 (12)
H33	0.7061	0.3326	0.2623	0.050*
C35	0.6222 (5)	0.4465 (3)	0.3979 (4)	0.0531 (15)
H35	0.6027	0.4970	0.4038	0.064*
C36	0.6125 (5)	0.3970 (3)	0.4643 (4)	0.0460 (13)
H36	0.5858	0.4141	0.5147	0.055*
C34	0.6599 (5)	0.4236 (3)	0.3232 (4)	0.0453 (13)
C341	0.6776 (6)	0.4776 (4)	0.2548 (4)	0.0725 (19)
H34A	0.6564	0.5271	0.2717	0.109*	0.50
H34B	0.6271	0.4641	0.1978	0.109*	0.50
H34C	0.7608	0.4770	0.2500	0.109*	0.50
H34D	0.7065	0.4517	0.2080	0.109*	0.50
H34E	0.7358	0.5147	0.2818	0.109*	0.50
H34F	0.6020	0.5018	0.2297	0.109*	0.50
C61	1.0491 (4)	0.3112 (2)	0.5556 (3)	0.0265 (9)
C62	1.1662 (4)	0.3171 (3)	0.5484 (3)	0.0412 (12)
H62	1.2246	0.2861	0.5828	0.049*
C64	1.1176 (5)	0.4146 (3)	0.4397 (3)	0.0380 (12)
C65	1.0001 (4)	0.4079 (3)	0.4464 (3)	0.0374 (12)
H65	0.9417	0.4386	0.4113	0.045*
C641	1.1555 (5)	0.4692 (3)	0.3780 (4)	0.0539 (15)
H64A	1.0863	0.4972	0.3472	0.081*	0.50
H64B	1.1909	0.4429	0.3348	0.081*	0.50
H64C	1.2139	0.5033	0.4119	0.081*	0.50
H64D	1.2411	0.4650	0.3821	0.081*	0.50
H64E	1.1365	0.5193	0.3945	0.081*	0.50
H64F	1.1135	0.4589	0.3173	0.081*	0.50
C63	1.1987 (5)	0.3684 (3)	0.4910 (4)	0.0478 (14)
H63	1.2796	0.3716	0.4872	0.057*
C66	0.9665 (4)	0.3571 (2)	0.5034 (3)	0.0325 (11)
H66	0.8855	0.3536	0.5068	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu	0.0203 (3)	0.0198 (3)	0.0476 (4)	0.0012 (2)	0.0076 (2)	0.0030 (3)
P2	0.0213 (6)	0.0209 (6)	0.0355 (7)	0.0000 (5)	0.0078 (5)	−0.0028 (5)
Cl	0.0283 (6)	0.0228 (6)	0.0683 (9)	−0.0031 (5)	0.0116 (6)	−0.0042 (6)
P1	0.0201 (6)	0.0181 (6)	0.0612 (9)	0.0005 (5)	0.0057 (6)	0.0012 (6)
C41	0.024 (2)	0.030 (2)	0.032 (2)	−0.0027 (19)	0.0081 (19)	0.002 (2)
C42	0.024 (2)	0.034 (3)	0.044 (3)	−0.003 (2)	0.008 (2)	−0.005 (2)
C46	0.029 (2)	0.030 (3)	0.040 (3)	−0.002 (2)	0.001 (2)	−0.003 (2)
C43	0.020 (2)	0.041 (3)	0.044 (3)	−0.003 (2)	−0.001 (2)	−0.001 (2)
C45	0.036 (3)	0.024 (2)	0.055 (3)	0.005 (2)	0.006 (2)	−0.005 (2)
C44	0.028 (3)	0.039 (3)	0.046 (3)	0.009 (2)	0.003 (2)	0.003 (2)
C51	0.020 (2)	0.028 (2)	0.033 (2)	0.0027 (19)	0.0047 (18)	−0.001 (2)
C52	0.034 (2)	0.028 (2)	0.031 (3)	0.002 (2)	0.009 (2)	−0.001 (2)
C56	0.033 (3)	0.032 (3)	0.042 (3)	0.005 (2)	0.014 (2)	0.009 (2)
C54	0.038 (3)	0.041 (3)	0.037 (3)	0.016 (2)	0.008 (2)	−0.005 (2)
C53	0.040 (3)	0.028 (3)	0.039 (3)	0.001 (2)	0.005 (2)	−0.006 (2)
C55	0.045 (3)	0.046 (3)	0.035 (3)	0.014 (3)	0.014 (2)	0.011 (2)
C26	0.034 (3)	0.043 (3)	0.045 (3)	−0.010 (2)	0.004 (2)	0.004 (3)
C21	0.025 (2)	0.020 (2)	0.054 (3)	0.003 (2)	0.001 (2)	0.006 (2)
C22	0.026 (3)	0.031 (3)	0.107 (5)	0.002 (2)	0.005 (3)	−0.020 (3)
C25	0.046 (3)	0.040 (3)	0.062 (4)	−0.007 (3)	0.023 (3)	−0.003 (3)
C23	0.036 (3)	0.040 (3)	0.099 (5)	0.006 (3)	−0.011 (3)	−0.026 (3)
C24	0.054 (3)	0.031 (3)	0.052 (3)	0.006 (3)	0.006 (3)	−0.003 (2)
C11	0.022 (2)	0.020 (2)	0.054 (3)	−0.0037 (19)	0.009 (2)	−0.002 (2)
C12	0.024 (2)	0.026 (3)	0.089 (4)	0.002 (2)	0.007 (3)	0.005 (3)
C15	0.028 (3)	0.049 (3)	0.045 (3)	−0.006 (2)	0.002 (2)	−0.006 (3)
C16	0.030 (2)	0.029 (2)	0.049 (3)	−0.002 (2)	0.010 (2)	0.002 (2)
C13	0.036 (3)	0.026 (3)	0.106 (5)	−0.003 (2)	0.021 (3)	−0.002 (3)
C14	0.027 (3)	0.041 (3)	0.061 (3)	−0.013 (2)	0.015 (2)	−0.014 (3)
C31	0.022 (2)	0.023 (2)	0.057 (3)	−0.0010 (19)	0.007 (2)	−0.002 (2)
C32	0.027 (2)	0.029 (3)	0.065 (3)	−0.002 (2)	−0.002 (2)	−0.006 (3)
C33	0.036 (3)	0.037 (3)	0.051 (3)	0.001 (2)	0.008 (2)	−0.001 (3)
C35	0.070 (4)	0.022 (3)	0.075 (4)	0.006 (3)	0.033 (3)	0.008 (3)
C36	0.049 (3)	0.030 (3)	0.064 (4)	0.008 (2)	0.024 (3)	0.006 (3)
C34	0.047 (3)	0.031 (3)	0.059 (3)	−0.006 (2)	0.015 (3)	0.004 (3)
C341	0.081 (5)	0.065 (4)	0.078 (5)	−0.004 (4)	0.033 (4)	0.007 (4)
C61	0.028 (2)	0.022 (2)	0.030 (2)	−0.0003 (19)	0.0086 (19)	−0.0088 (19)
C62	0.037 (3)	0.040 (3)	0.052 (3)	0.012 (2)	0.020 (2)	0.013 (2)
C64	0.052 (3)	0.031 (3)	0.036 (3)	−0.001 (2)	0.020 (2)	−0.001 (2)
C65	0.045 (3)	0.028 (3)	0.037 (3)	0.000 (2)	0.003 (2)	0.003 (2)
C641	0.069 (4)	0.046 (3)	0.053 (3)	0.011 (3)	0.029 (3)	0.013 (3)
C63	0.044 (3)	0.050 (3)	0.058 (4)	0.012 (3)	0.028 (3)	0.014 (3)
C66	0.030 (2)	0.030 (2)	0.038 (3)	−0.004 (2)	0.008 (2)	0.000 (2)

Geometric parameters (Å, º)

Cu—Cl	2.2330 (12)	C12—C13	1.380 (7)
Cu—P1	2.2570 (13)	C12—H12	0.9500
Cu—P2	2.2579 (12)	C15—C14	1.372 (7)
P2—C41	1.818 (4)	C15—C16	1.388 (6)
P2—C61	1.820 (4)	C15—H15	0.9500
P2—C51	1.823 (4)	C16—H16	0.9500
P1—C31	1.811 (5)	C13—C14	1.365 (7)
P1—C21	1.818 (5)	C13—H13	0.9500
P1—C11	1.823 (4)	C14—H14	0.9500
C41—C46	1.391 (6)	C31—C32	1.390 (7)
C41—C42	1.397 (6)	C31—C36	1.397 (6)
C42—C43	1.385 (6)	C32—C33	1.390 (7)
C42—H42	0.9500	C32—H32	0.9500
C46—C45	1.391 (6)	C33—C34	1.375 (7)
C46—H46	0.9500	C33—H33	0.9500
C43—C44	1.367 (7)	C35—C34	1.384 (7)
C43—H43	0.9500	C35—C36	1.388 (7)
C45—C44	1.386 (7)	C35—H35	0.9500
C45—H45	0.9500	C36—H36	0.9500
C44—H44	0.9500	C34—C341	1.487 (8)
C51—C56	1.395 (6)	C341—H34A	0.9800
C51—C52	1.396 (6)	C341—H34B	0.9800
C52—C53	1.386 (6)	C341—H34C	0.9800
C52—H52	0.9500	C341—H34D	0.9800
C56—C55	1.377 (7)	C341—H34E	0.9800
C56—H56	0.9500	C341—H34F	0.9800
C54—C53	1.383 (7)	C61—C62	1.383 (6)
C54—C55	1.387 (7)	C61—C66	1.388 (6)
C54—H54	0.9500	C62—C63	1.391 (7)
C53—H53	0.9500	C62—H62	0.9500
C55—H55	0.9500	C64—C63	1.375 (7)
C26—C25	1.376 (7)	C64—C65	1.388 (7)
C26—C21	1.394 (6)	C64—C641	1.503 (7)
C26—H26	0.9500	C65—C66	1.387 (6)
C21—C22	1.387 (7)	C65—H65	0.9500
C22—C23	1.364 (8)	C641—H64A	0.9800
C22—H22	0.9500	C641—H64B	0.9800
C25—C24	1.383 (7)	C641—H64C	0.9800
C25—H25	0.9500	C641—H64D	0.9800
C23—C24	1.364 (8)	C641—H64E	0.9800
C23—H23	0.9500	C641—H64F	0.9800
C24—H24	0.9500	C63—H63	0.9500
C11—C16	1.383 (6)	C66—H66	0.9500
C11—C12	1.390 (6)
Cl—Cu—P1	114.95 (5)	C12—C13—H13	119.4
Cl—Cu—P2	118.26 (5)	C13—C14—C15	119.2 (5)
P1—Cu—P2	126.72 (5)	C13—C14—H14	120.4
C41—P2—C61	104.01 (19)	C15—C14—H14	120.4
C41—P2—C51	103.6 (2)	C32—C31—C36	116.4 (5)
C61—P2—C51	103.0 (2)	C32—C31—P1	118.5 (4)
C41—P2—Cu	117.03 (15)	C36—C31—P1	125.0 (4)
C61—P2—Cu	113.26 (14)	C31—C32—C33	122.6 (5)
C51—P2—Cu	114.38 (14)	C31—C32—H32	118.7
C31—P1—C21	104.8 (2)	C33—C32—H32	118.7
C31—P1—C11	104.1 (2)	C34—C33—C32	120.0 (5)
C21—P1—C11	103.9 (2)	C34—C33—H33	120.0
C31—P1—Cu	111.26 (15)	C32—C33—H33	120.0
C21—P1—Cu	114.38 (15)	C34—C35—C36	121.0 (5)
C11—P1—Cu	117.15 (15)	C34—C35—H35	119.5
C46—C41—C42	118.6 (4)	C36—C35—H35	119.5
C46—C41—P2	118.6 (3)	C35—C36—C31	121.3 (5)
C42—C41—P2	122.8 (3)	C35—C36—H36	119.4
C43—C42—C41	120.7 (4)	C31—C36—H36	119.4
C43—C42—H42	119.7	C33—C34—C35	118.7 (5)
C41—C42—H42	119.7	C33—C34—C341	120.5 (5)
C41—C46—C45	120.2 (4)	C35—C34—C341	120.8 (5)
C41—C46—H46	119.9	C34—C341—H34A	109.5
C45—C46—H46	119.9	C34—C341—H34B	109.5
C44—C43—C42	120.3 (4)	H34A—C341—H34B	109.5
C44—C43—H43	119.9	C34—C341—H34C	109.5
C42—C43—H43	119.9	H34A—C341—H34C	109.5
C44—C45—C46	120.1 (4)	H34B—C341—H34C	109.5
C44—C45—H45	119.9	C34—C341—H34D	109.5
C46—C45—H45	119.9	H34A—C341—H34D	141.1
C43—C44—C45	120.1 (4)	H34B—C341—H34D	56.3
C43—C44—H44	120.0	H34C—C341—H34D	56.3
C45—C44—H44	120.0	C34—C341—H34E	109.5
C56—C51—C52	118.5 (4)	H34A—C341—H34E	56.3
C56—C51—P2	118.6 (3)	H34B—C341—H34E	141.1
C52—C51—P2	122.7 (3)	H34C—C341—H34E	56.3
C53—C52—C51	120.8 (4)	H34D—C341—H34E	109.5
C53—C52—H52	119.6	C34—C341—H34F	109.5
C51—C52—H52	119.6	H34A—C341—H34F	56.3
C55—C56—C51	120.5 (5)	H34B—C341—H34F	56.3
C55—C56—H56	119.8	H34C—C341—H34F	141.1
C51—C56—H56	119.8	H34D—C341—H34F	109.5
C53—C54—C55	119.8 (5)	H34E—C341—H34F	109.5
C53—C54—H54	120.1	C62—C61—C66	118.0 (4)
C55—C54—H54	120.1	C62—C61—P2	122.8 (4)
C54—C53—C52	119.8 (5)	C66—C61—P2	119.1 (3)
C54—C53—H53	120.1	C61—C62—C63	120.3 (5)
C52—C53—H53	120.1	C61—C62—H62	119.9
C56—C55—C54	120.5 (5)	C63—C62—H62	119.9
C56—C55—H55	119.7	C63—C64—C65	117.4 (4)
C54—C55—H55	119.7	C63—C64—C641	120.9 (5)
C25—C26—C21	120.2 (5)	C65—C64—C641	121.7 (5)
C25—C26—H26	119.9	C66—C65—C64	121.0 (5)
C21—C26—H26	119.9	C66—C65—H65	119.5
C22—C21—C26	117.1 (5)	C64—C65—H65	119.5
C22—C21—P1	119.1 (4)	C64—C641—H64A	109.5
C26—C21—P1	123.6 (4)	C64—C641—H64B	109.5
C23—C22—C21	122.4 (5)	H64A—C641—H64B	109.5
C23—C22—H22	118.8	C64—C641—H64C	109.5
C21—C22—H22	118.8	H64A—C641—H64C	109.5
C26—C25—C24	121.3 (5)	H64B—C641—H64C	109.5
C26—C25—H25	119.4	C64—C641—H64D	109.5
C24—C25—H25	119.4	H64A—C641—H64D	141.1
C22—C23—C24	120.3 (5)	H64B—C641—H64D	56.3
C22—C23—H23	119.9	H64C—C641—H64D	56.3
C24—C23—H23	119.9	C64—C641—H64E	109.5
C23—C24—C25	118.8 (5)	H64A—C641—H64E	56.3
C23—C24—H24	120.6	H64B—C641—H64E	141.1
C25—C24—H24	120.6	H64C—C641—H64E	56.3
C16—C11—C12	118.6 (4)	H64D—C641—H64E	109.5
C16—C11—P1	122.5 (3)	C64—C641—H64F	109.5
C12—C11—P1	118.8 (4)	H64A—C641—H64F	56.3
C13—C12—C11	120.0 (5)	H64B—C641—H64F	56.3
C13—C12—H12	120.0	H64C—C641—H64F	141.1
C11—C12—H12	120.0	H64D—C641—H64F	109.5
C14—C15—C16	120.5 (5)	H64E—C641—H64F	109.5
C14—C15—H15	119.8	C64—C63—C62	122.1 (5)
C16—C15—H15	119.8	C64—C63—H63	118.9
C11—C16—C15	120.4 (5)	C62—C63—H63	118.9
C11—C16—H16	119.8	C65—C66—C61	121.2 (4)
C15—C16—H16	119.8	C65—C66—H66	119.4
C14—C13—C12	121.2 (5)	C61—C66—H66	119.4
C14—C13—H13	119.4
Cl—Cu—P2—C41	−11.46 (17)	C21—C26—C25—C24	−0.1 (8)
P1—Cu—P2—C41	171.72 (16)	C21—C22—C23—C24	1.7 (9)
Cl—Cu—P2—C61	109.55 (15)	C22—C23—C24—C25	−0.9 (9)
P1—Cu—P2—C61	−67.27 (16)	C26—C25—C24—C23	0.2 (8)
Cl—Cu—P2—C51	−132.83 (16)	C31—P1—C11—C16	−34.0 (5)
P1—Cu—P2—C51	50.35 (17)	C21—P1—C11—C16	75.5 (4)
Cl—Cu—P1—C31	−113.71 (17)	Cu—P1—C11—C16	−157.3 (4)
P2—Cu—P1—C31	63.21 (18)	C31—P1—C11—C12	149.2 (4)
Cl—Cu—P1—C21	127.72 (17)	C21—P1—C11—C12	−101.3 (4)
P2—Cu—P1—C21	−55.37 (18)	Cu—P1—C11—C12	26.0 (5)
Cl—Cu—P1—C11	5.79 (19)	C16—C11—C12—C13	−0.5 (8)
P2—Cu—P1—C11	−177.30 (18)	P1—C11—C12—C13	176.4 (4)
C61—P2—C41—C46	−98.9 (4)	C12—C11—C16—C15	0.6 (7)
C51—P2—C41—C46	153.7 (4)	P1—C11—C16—C15	−176.1 (4)
Cu—P2—C41—C46	26.8 (4)	C14—C15—C16—C11	−0.5 (7)
C61—P2—C41—C42	78.1 (4)	C11—C12—C13—C14	0.2 (9)
C51—P2—C41—C42	−29.2 (4)	C12—C13—C14—C15	−0.1 (9)
Cu—P2—C41—C42	−156.1 (3)	C16—C15—C14—C13	0.3 (8)
C46—C41—C42—C43	1.7 (7)	C21—P1—C31—C32	174.5 (4)
P2—C41—C42—C43	−175.4 (3)	C11—P1—C31—C32	−76.7 (4)
C42—C41—C46—C45	−1.8 (7)	Cu—P1—C31—C32	50.3 (4)
P2—C41—C46—C45	175.4 (4)	C21—P1—C31—C36	−1.5 (5)
C41—C42—C43—C44	−1.0 (7)	C11—P1—C31—C36	107.3 (4)
C41—C46—C45—C44	1.3 (7)	Cu—P1—C31—C36	−125.6 (4)
C42—C43—C44—C45	0.4 (7)	C36—C31—C32—C33	1.7 (7)
C46—C45—C44—C43	−0.6 (8)	P1—C31—C32—C33	−174.6 (4)
C41—P2—C51—C56	−75.3 (4)	C31—C32—C33—C34	1.0 (7)
C61—P2—C51—C56	176.6 (3)	C34—C35—C36—C31	0.5 (9)
Cu—P2—C51—C56	53.2 (4)	C32—C31—C36—C35	−2.4 (8)
C41—P2—C51—C52	108.2 (4)	P1—C31—C36—C35	173.6 (4)
C61—P2—C51—C52	0.1 (4)	C32—C33—C34—C35	−2.9 (8)
Cu—P2—C51—C52	−123.3 (3)	C32—C33—C34—C341	175.4 (5)
C56—C51—C52—C53	−1.4 (6)	C36—C35—C34—C33	2.3 (9)
P2—C51—C52—C53	175.1 (3)	C36—C35—C34—C341	−176.1 (6)
C52—C51—C56—C55	1.1 (7)	C41—P2—C61—C62	−14.8 (4)
P2—C51—C56—C55	−175.6 (4)	C51—P2—C61—C62	93.0 (4)
C55—C54—C53—C52	1.2 (7)	Cu—P2—C61—C62	−142.9 (4)
C51—C52—C53—C54	0.3 (7)	C41—P2—C61—C66	167.3 (3)
C51—C56—C55—C54	0.3 (7)	C51—P2—C61—C66	−84.9 (4)
C53—C54—C55—C56	−1.5 (7)	Cu—P2—C61—C66	39.2 (4)
C25—C26—C21—C22	0.8 (7)	C66—C61—C62—C63	0.7 (7)
C25—C26—C21—P1	176.7 (4)	P2—C61—C62—C63	−177.2 (4)
C31—P1—C21—C22	−76.8 (4)	C63—C64—C65—C66	0.6 (7)
C11—P1—C21—C22	174.3 (4)	C641—C64—C65—C66	179.9 (5)
Cu—P1—C21—C22	45.3 (4)	C65—C64—C63—C62	−0.6 (8)
C31—P1—C21—C26	107.4 (4)	C641—C64—C63—C62	−179.8 (5)
C11—P1—C21—C26	−1.6 (5)	C61—C62—C63—C64	−0.1 (8)
Cu—P1—C21—C26	−130.5 (4)	C64—C65—C66—C61	0.0 (7)
C26—C21—C22—C23	−1.6 (8)	C62—C61—C66—C65	−0.6 (7)
P1—C21—C22—C23	−177.7 (5)	P2—C61—C66—C65	177.3 (4)