(3-Acetyl­pyridine-κN)chloro­bis(triphenylphosphine-κP)copper(I): a suitable candidate for absolute asymmetric synthesis?

It was found that 3-acetyl­pyridine is capable of displacing triphenyl­phosphine from [CuCl(PPh₃)₃], forming the title compound, [CuCl(C₇H₇NO)(C₁₈H₁₅P)₂]. The two triphenyl­phosphine ligands possess the same sense of chirality, and the mol­ecules are therefore conformationally chiral. The compound was found to crystallize as a racemate (centrosymmetric space group) under the crystallization conditions employed. The mol­ecular structure shows that the carbonyl C atom is blocked at one side by a triphenyl­phosphine ligand, while the other face is open for nucleophilic attack. Obtaining chiral crystals of the title compound is thus a future objective. In the crystal structure, C—H...O(=C)-bonded dimers are formed, which are further stabilized by π–π inter­actions. The dimers form infinite chains through weak C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 290 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.064
• wR factor = 0.139
• Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Cu1    -   P1      ..      10.28 su

Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    -   P2      ..       6.39 su

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   1 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
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLUTON (Spek, 2003); software used to prepare material for publication: SHELXL97.

(3-Acetylpyridine-κN)chlorobis(triphenylphosphine-κP)copper(I)

Crystal data

[CuCl(C7H7NO)(C18H15P)2]	F(000) = 1544
Mr = 744.68	Dx = 1.376 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6651 reflections
a = 9.7903 (18) Å	θ = 2.3–25.5°
b = 37.266 (6) Å	µ = 0.81 mm^−1
c = 10.917 (2) Å	T = 290 K
β = 115.547 (5)°	Block, yellow
V = 3593.6 (11) Å^3	0.2 × 0.2 × 0.1 mm
Z = 4

Data collection

Rigaku R-AXIS IIC image-plate diffractometer	7029 independent reflections
Radiation source: rotating-anode X-ray tube, Rigaku RU-H3R	5490 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.094
Detector resolution: 105 pixels mm^-1	θmax = 26.0°, θmin = 2.3°
φ scans	h = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000)	k = −45→45
Tmin = 0.836, Tmax = 0.919	l = −13→13
25365 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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.139	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0575P)^2 + 0.8762P] where P = (Fo^2 + 2Fc^2)/3
7029 reflections	(Δ/σ)max < 0.001
442 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.41 e Å^−3

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

	x	y	z	Uiso*/Ueq
O1	0.7975 (4)	0.06335 (9)	0.0149 (3)	0.0654 (9)
C1	0.5773 (4)	0.05788 (9)	0.3086 (4)	0.0301 (7)
C2	0.5129 (4)	0.07887 (10)	0.1945 (4)	0.0399 (9)
H2	0.5312	0.1034	0.2012	0.048*
C3	0.4211 (5)	0.06405 (12)	0.0697 (4)	0.0524 (11)
H3	0.3787	0.0785	−0.0070	0.063*
C4	0.3932 (5)	0.02797 (13)	0.0599 (5)	0.0579 (12)
H4	0.3301	0.0179	−0.0234	0.070*
C5	0.4580 (5)	0.00652 (11)	0.1728 (5)	0.0513 (11)
H5	0.4399	−0.0181	0.1656	0.062*
C6	0.5497 (5)	0.02143 (10)	0.2964 (4)	0.0412 (9)
H6	0.5935	0.0068	0.3726	0.049*
C7	0.5518 (4)	0.08206 (9)	0.5451 (4)	0.0307 (7)
C8	0.3992 (4)	0.07598 (10)	0.4712 (4)	0.0429 (9)
H8	0.3620	0.0692	0.3805	0.052*
C9	0.3015 (5)	0.07982 (12)	0.5305 (5)	0.0550 (11)
H9	0.1986	0.0758	0.4792	0.066*
C10	0.3541 (5)	0.08947 (11)	0.6645 (5)	0.0511 (11)
H10	0.2875	0.0920	0.7042	0.061*
C11	0.5048 (5)	0.09532 (11)	0.7385 (4)	0.0504 (11)
H11	0.5415	0.1016	0.8296	0.060*
C12	0.6034 (5)	0.09208 (10)	0.6797 (4)	0.0436 (9)
H12	0.7059	0.0967	0.7310	0.052*
C13	0.8214 (4)	0.04642 (9)	0.5738 (3)	0.0305 (8)
C14	0.7856 (5)	0.01905 (10)	0.6407 (4)	0.0425 (9)
H14	0.6882	0.0175	0.6351	0.051*
C15	0.8933 (5)	−0.00595 (11)	0.7156 (4)	0.0535 (12)
H15	0.8681	−0.0244	0.7595	0.064*
C16	1.0378 (5)	−0.00369 (10)	0.7256 (5)	0.0525 (11)
H16	1.1105	−0.0205	0.7765	0.063*
C17	1.0742 (5)	0.02323 (11)	0.6606 (5)	0.0545 (12)
H17	1.1713	0.0246	0.6656	0.065*
C18	0.9668 (4)	0.04855 (10)	0.5870 (4)	0.0417 (9)
H18	0.9938	0.0674	0.5459	0.050*
C19	0.7798 (4)	0.22607 (9)	0.4014 (4)	0.0319 (8)
C20	0.8969 (5)	0.23137 (11)	0.5293 (4)	0.0488 (10)
H20	0.9208	0.2136	0.5952	0.059*
C21	0.9783 (5)	0.26308 (13)	0.5586 (5)	0.0629 (13)
H21	1.0560	0.2667	0.6448	0.075*
C22	0.9454 (6)	0.28903 (12)	0.4622 (6)	0.0622 (13)
H22	1.0009	0.3102	0.4828	0.075*
C23	0.8314 (6)	0.28412 (11)	0.3356 (5)	0.0578 (12)
H23	0.8100	0.3018	0.2697	0.069*
C24	0.7479 (5)	0.25275 (10)	0.3054 (4)	0.0466 (10)
H24	0.6693	0.2496	0.2193	0.056*
C25	0.5301 (4)	0.20016 (9)	0.4375 (3)	0.0308 (8)
C26	0.4431 (5)	0.23056 (10)	0.3908 (4)	0.0465 (10)
H26	0.4536	0.2445	0.3247	0.056*
C27	0.3410 (5)	0.24068 (12)	0.4399 (5)	0.0565 (12)
H27	0.2830	0.2613	0.4073	0.068*
C28	0.3256 (5)	0.22008 (13)	0.5378 (5)	0.0592 (13)
H28	0.2563	0.2266	0.5712	0.071*
C29	0.4110 (6)	0.19050 (14)	0.5851 (5)	0.0597 (12)
H29	0.4015	0.1769	0.6524	0.072*
C30	0.5124 (5)	0.18003 (11)	0.5353 (4)	0.0448 (10)
H30	0.5692	0.1592	0.5680	0.054*
C31	0.5588 (4)	0.18120 (8)	0.1946 (3)	0.0289 (7)
C32	0.4056 (4)	0.17333 (9)	0.1389 (4)	0.0364 (8)
H32	0.3548	0.1738	0.1939	0.044*
C33	0.3267 (4)	0.16475 (10)	0.0026 (4)	0.0418 (9)
H33	0.2240	0.1593	−0.0334	0.050*
C34	0.4015 (5)	0.16440 (11)	−0.0785 (4)	0.0465 (10)
H34	0.3494	0.1586	−0.1700	0.056*
C35	0.5535 (5)	0.17259 (12)	−0.0251 (4)	0.0496 (10)
H35	0.6032	0.1726	−0.0810	0.059*
C36	0.6323 (4)	0.18076 (10)	0.1106 (4)	0.0403 (9)
H36	0.7351	0.1860	0.1461	0.048*
C37	0.8865 (4)	0.10706 (10)	0.2417 (4)	0.0370 (8)
H37	0.8045	0.0917	0.2201	0.044*
C38	0.9621 (4)	0.10614 (9)	0.1602 (4)	0.0358 (8)
C39	1.0826 (5)	0.12875 (12)	0.1926 (5)	0.0530 (11)
H39	1.1388	0.1285	0.1424	0.064*
C40	1.1199 (5)	0.15199 (13)	0.3008 (5)	0.0592 (13)
H40	1.1982	0.1684	0.3214	0.071*
C41	1.0402 (5)	0.15063 (11)	0.3776 (5)	0.0501 (11)
H41	1.0686	0.1657	0.4525	0.060*
C42	0.9111 (5)	0.08047 (11)	0.0442 (4)	0.0449 (10)
C43	1.0036 (6)	0.07637 (15)	−0.0336 (5)	0.0701 (14)
H43A	0.9670	0.0563	−0.0941	0.105*
H43B	1.1075	0.0724	0.0284	0.105*
H43C	0.9956	0.0978	−0.0852	0.105*
Cu1	0.79726 (5)	0.133715 (11)	0.46803 (4)	0.03251 (14)
N1	0.9229 (3)	0.12835 (8)	0.3488 (3)	0.0361 (7)
P1	0.68671 (10)	0.08041 (2)	0.47080 (9)	0.0277 (2)
P2	0.66872 (10)	0.18539 (2)	0.37794 (9)	0.0289 (2)
Cl1	0.98779 (13)	0.14222 (3)	0.68515 (11)	0.0548 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.066 (2)	0.075 (2)	0.052 (2)	−0.0210 (18)	0.0234 (18)	−0.0146 (16)
C1	0.0257 (18)	0.0356 (18)	0.0307 (19)	−0.0005 (14)	0.0139 (15)	−0.0020 (15)
C2	0.037 (2)	0.042 (2)	0.038 (2)	−0.0058 (16)	0.0135 (18)	−0.0021 (17)
C3	0.051 (3)	0.061 (3)	0.038 (2)	0.000 (2)	0.012 (2)	0.002 (2)
C4	0.052 (3)	0.072 (3)	0.043 (3)	−0.008 (2)	0.014 (2)	−0.025 (2)
C5	0.052 (3)	0.044 (2)	0.059 (3)	−0.0094 (19)	0.024 (2)	−0.014 (2)
C6	0.047 (2)	0.036 (2)	0.041 (2)	−0.0002 (17)	0.0190 (19)	−0.0016 (16)
C7	0.0326 (19)	0.0269 (17)	0.037 (2)	0.0010 (14)	0.0193 (16)	0.0003 (14)
C8	0.033 (2)	0.053 (2)	0.043 (2)	−0.0049 (17)	0.0171 (19)	−0.0079 (18)
C9	0.035 (2)	0.071 (3)	0.067 (3)	−0.009 (2)	0.029 (2)	−0.009 (2)
C10	0.055 (3)	0.049 (2)	0.069 (3)	0.002 (2)	0.045 (3)	0.000 (2)
C11	0.059 (3)	0.057 (3)	0.043 (2)	0.007 (2)	0.029 (2)	−0.0041 (19)
C12	0.038 (2)	0.052 (2)	0.040 (2)	0.0020 (17)	0.0156 (19)	−0.0041 (18)
C13	0.0299 (19)	0.0294 (17)	0.0287 (19)	−0.0025 (14)	0.0093 (15)	−0.0013 (14)
C14	0.036 (2)	0.043 (2)	0.048 (2)	−0.0031 (17)	0.0172 (19)	0.0068 (18)
C15	0.060 (3)	0.038 (2)	0.053 (3)	−0.0045 (19)	0.015 (2)	0.0150 (19)
C16	0.047 (3)	0.038 (2)	0.055 (3)	0.0099 (18)	0.005 (2)	0.0053 (19)
C17	0.035 (2)	0.050 (2)	0.074 (3)	0.0074 (18)	0.020 (2)	0.011 (2)
C18	0.032 (2)	0.040 (2)	0.054 (3)	0.0040 (16)	0.0193 (19)	0.0108 (18)
C19	0.0315 (19)	0.0319 (18)	0.035 (2)	−0.0012 (14)	0.0167 (16)	−0.0011 (15)
C20	0.047 (3)	0.046 (2)	0.045 (2)	−0.0069 (18)	0.012 (2)	−0.0020 (18)
C21	0.046 (3)	0.064 (3)	0.061 (3)	−0.015 (2)	0.007 (2)	−0.016 (2)
C22	0.057 (3)	0.048 (3)	0.086 (4)	−0.022 (2)	0.035 (3)	−0.014 (3)
C23	0.071 (3)	0.044 (2)	0.066 (3)	−0.011 (2)	0.037 (3)	0.001 (2)
C24	0.050 (3)	0.042 (2)	0.049 (3)	−0.0077 (18)	0.022 (2)	0.0007 (19)
C25	0.0295 (19)	0.0320 (18)	0.0301 (19)	−0.0044 (14)	0.0120 (16)	−0.0060 (14)
C26	0.053 (3)	0.038 (2)	0.053 (3)	0.0002 (18)	0.027 (2)	0.0017 (18)
C27	0.052 (3)	0.045 (2)	0.074 (3)	0.004 (2)	0.029 (3)	−0.018 (2)
C28	0.054 (3)	0.071 (3)	0.069 (3)	−0.013 (2)	0.042 (3)	−0.034 (3)
C29	0.072 (3)	0.076 (3)	0.049 (3)	−0.010 (3)	0.043 (3)	−0.006 (2)
C30	0.055 (3)	0.048 (2)	0.038 (2)	−0.0033 (19)	0.026 (2)	−0.0014 (17)
C31	0.0324 (19)	0.0278 (17)	0.0241 (18)	−0.0003 (14)	0.0100 (15)	0.0024 (13)
C32	0.037 (2)	0.042 (2)	0.033 (2)	−0.0033 (16)	0.0185 (17)	−0.0001 (16)
C33	0.037 (2)	0.048 (2)	0.032 (2)	−0.0052 (17)	0.0074 (18)	−0.0033 (16)
C34	0.054 (3)	0.057 (3)	0.026 (2)	0.000 (2)	0.0149 (19)	−0.0050 (17)
C35	0.057 (3)	0.068 (3)	0.035 (2)	0.000 (2)	0.030 (2)	−0.003 (2)
C36	0.037 (2)	0.051 (2)	0.036 (2)	−0.0005 (17)	0.0190 (18)	0.0005 (17)
C37	0.0294 (19)	0.040 (2)	0.042 (2)	−0.0043 (15)	0.0164 (17)	−0.0006 (16)
C38	0.035 (2)	0.037 (2)	0.035 (2)	0.0025 (16)	0.0150 (17)	0.0033 (15)
C39	0.050 (3)	0.070 (3)	0.052 (3)	−0.011 (2)	0.034 (2)	−0.002 (2)
C40	0.055 (3)	0.071 (3)	0.065 (3)	−0.027 (2)	0.039 (3)	−0.016 (2)
C41	0.047 (3)	0.053 (3)	0.056 (3)	−0.0136 (19)	0.028 (2)	−0.015 (2)
C42	0.046 (2)	0.052 (2)	0.032 (2)	0.004 (2)	0.0123 (19)	0.0052 (18)
C43	0.071 (4)	0.096 (4)	0.052 (3)	−0.002 (3)	0.035 (3)	−0.016 (3)
Cu1	0.0301 (2)	0.0324 (2)	0.0344 (3)	−0.00223 (18)	0.01334 (19)	−0.00039 (18)
N1	0.0352 (17)	0.0375 (17)	0.0409 (19)	−0.0027 (13)	0.0213 (15)	−0.0034 (14)
P1	0.0250 (5)	0.0273 (4)	0.0310 (5)	−0.0020 (3)	0.0122 (4)	−0.0002 (4)
P2	0.0290 (5)	0.0296 (5)	0.0277 (5)	−0.0010 (4)	0.0119 (4)	0.0003 (3)
Cl1	0.0524 (7)	0.0517 (6)	0.0391 (6)	0.0012 (5)	−0.0001 (5)	−0.0063 (4)

Geometric parameters (Å, º)

O1—C42	1.200 (5)	C23—C24	1.383 (6)
C1—C2	1.373 (5)	C23—H23	0.9300
C1—C6	1.380 (5)	C24—H24	0.9300
C1—P1	1.830 (4)	C25—C30	1.376 (5)
C2—C3	1.383 (6)	C25—C26	1.376 (5)
C2—H2	0.9300	C25—P2	1.825 (4)
C3—C4	1.367 (6)	C26—C27	1.375 (6)
C3—H3	0.9300	C26—H26	0.9300
C4—C5	1.373 (6)	C27—C28	1.376 (7)
C4—H4	0.9300	C27—H27	0.9300
C5—C6	1.375 (6)	C28—C29	1.345 (7)
C5—H5	0.9300	C28—H28	0.9300
C6—H6	0.9300	C29—C30	1.378 (6)
C7—C8	1.376 (5)	C29—H29	0.9300
C7—C12	1.383 (5)	C30—H30	0.9300
C7—P1	1.825 (3)	C31—C32	1.385 (5)
C8—C9	1.374 (5)	C31—C36	1.389 (5)
C8—H8	0.9300	C31—P2	1.825 (3)
C9—C10	1.374 (6)	C32—C33	1.386 (5)
C9—H9	0.9300	C32—H32	0.9300
C10—C11	1.359 (6)	C33—C34	1.371 (6)
C10—H10	0.9300	C33—H33	0.9300
C11—C12	1.376 (6)	C34—C35	1.378 (6)
C11—H11	0.9300	C34—H34	0.9300
C12—H12	0.9300	C35—C36	1.377 (5)
C13—C18	1.370 (5)	C35—H35	0.9300
C13—C14	1.385 (5)	C36—H36	0.9300
C13—P1	1.824 (3)	C37—N1	1.328 (5)
C14—C15	1.381 (6)	C37—C38	1.381 (5)
C14—H14	0.9300	C37—H37	0.9300
C15—C16	1.374 (6)	C38—C39	1.366 (5)
C15—H15	0.9300	C38—C42	1.491 (5)
C16—C17	1.362 (6)	C39—C40	1.381 (6)
C16—H16	0.9300	C39—H39	0.9300
C17—C18	1.383 (5)	C40—C41	1.370 (6)
C17—H17	0.9300	C40—H40	0.9300
C18—H18	0.9300	C41—N1	1.340 (5)
C19—C24	1.380 (5)	C41—H41	0.9300
C19—C20	1.386 (5)	C42—C43	1.492 (6)
C19—P2	1.818 (3)	C43—H43A	0.9600
C20—C21	1.383 (6)	C43—H43B	0.9600
C20—H20	0.9300	C43—H43C	0.9600
C21—C22	1.362 (7)	Cu1—N1	2.151 (3)
C21—H21	0.9300	Cu1—P1	2.2687 (10)
C22—C23	1.363 (7)	Cu1—P2	2.2784 (10)
C22—H22	0.9300	Cu1—Cl1	2.3205 (11)
C2—C1—C6	118.6 (3)	C25—C26—H26	119.4
C2—C1—P1	117.7 (3)	C26—C27—C28	119.5 (4)
C6—C1—P1	123.6 (3)	C26—C27—H27	120.3
C1—C2—C3	121.1 (4)	C28—C27—H27	120.3
C1—C2—H2	119.5	C29—C28—C27	119.8 (4)
C3—C2—H2	119.5	C29—C28—H28	120.1
C4—C3—C2	119.5 (4)	C27—C28—H28	120.1
C4—C3—H3	120.2	C28—C29—C30	121.0 (4)
C2—C3—H3	120.2	C28—C29—H29	119.5
C3—C4—C5	120.2 (4)	C30—C29—H29	119.5
C3—C4—H4	119.9	C25—C30—C29	120.3 (4)
C5—C4—H4	119.9	C25—C30—H30	119.8
C4—C5—C6	119.9 (4)	C29—C30—H30	119.8
C4—C5—H5	120.0	C32—C31—C36	118.6 (3)
C6—C5—H5	120.0	C32—C31—P2	120.9 (3)
C5—C6—C1	120.7 (4)	C36—C31—P2	119.8 (3)
C5—C6—H6	119.7	C31—C32—C33	121.1 (3)
C1—C6—H6	119.7	C31—C32—H32	119.5
C8—C7—C12	118.3 (3)	C33—C32—H32	119.5
C8—C7—P1	123.0 (3)	C34—C33—C32	119.3 (4)
C12—C7—P1	118.6 (3)	C34—C33—H33	120.3
C9—C8—C7	120.4 (4)	C32—C33—H33	120.3
C9—C8—H8	119.8	C33—C34—C35	120.3 (4)
C7—C8—H8	119.8	C33—C34—H34	119.9
C10—C9—C8	120.8 (4)	C35—C34—H34	119.9
C10—C9—H9	119.6	C36—C35—C34	120.4 (4)
C8—C9—H9	119.6	C36—C35—H35	119.8
C11—C10—C9	119.1 (4)	C34—C35—H35	119.8
C11—C10—H10	120.4	C35—C36—C31	120.2 (4)
C9—C10—H10	120.4	C35—C36—H36	119.9
C10—C11—C12	120.6 (4)	C31—C36—H36	119.9
C10—C11—H11	119.7	N1—C37—C38	124.6 (3)
C12—C11—H11	119.7	N1—C37—H37	117.7
C11—C12—C7	120.7 (4)	C38—C37—H37	117.7
C11—C12—H12	119.6	C39—C38—C37	117.4 (4)
C7—C12—H12	119.6	C39—C38—C42	123.4 (4)
C18—C13—C14	118.4 (3)	C37—C38—C42	119.2 (3)
C18—C13—P1	117.8 (3)	C38—C39—C40	119.3 (4)
C14—C13—P1	123.8 (3)	C38—C39—H39	120.4
C15—C14—C13	120.5 (4)	C40—C39—H39	120.4
C15—C14—H14	119.8	C41—C40—C39	119.3 (4)
C13—C14—H14	119.8	C41—C40—H40	120.3
C16—C15—C14	120.2 (4)	C39—C40—H40	120.3
C16—C15—H15	119.9	N1—C41—C40	122.4 (4)
C14—C15—H15	119.9	N1—C41—H41	118.8
C17—C16—C15	119.7 (4)	C40—C41—H41	118.8
C17—C16—H16	120.1	O1—C42—C38	120.0 (4)
C15—C16—H16	120.1	O1—C42—C43	121.0 (4)
C16—C17—C18	120.1 (4)	C38—C42—C43	119.1 (4)
C16—C17—H17	120.0	C42—C43—H43A	109.5
C18—C17—H17	120.0	C42—C43—H43B	109.5
C13—C18—C17	121.1 (4)	H43A—C43—H43B	109.5
C13—C18—H18	119.4	C42—C43—H43C	109.5
C17—C18—H18	119.4	H43A—C43—H43C	109.5
C24—C19—C20	118.7 (3)	H43B—C43—H43C	109.5
C24—C19—P2	124.6 (3)	N1—Cu1—P1	109.10 (8)
C20—C19—P2	116.5 (3)	N1—Cu1—P2	99.83 (8)
C21—C20—C19	119.9 (4)	P1—Cu1—P2	124.61 (4)
C21—C20—H20	120.0	N1—Cu1—Cl1	102.32 (9)
C19—C20—H20	120.0	P1—Cu1—Cl1	106.49 (4)
C22—C21—C20	120.4 (4)	P2—Cu1—Cl1	112.12 (4)
C22—C21—H21	119.8	C37—N1—C41	117.0 (3)
C20—C21—H21	119.8	C37—N1—Cu1	125.6 (2)
C21—C22—C23	120.4 (4)	C41—N1—Cu1	117.1 (3)
C21—C22—H22	119.8	C13—P1—C7	102.63 (16)
C23—C22—H22	119.8	C13—P1—C1	104.10 (16)
C22—C23—C24	119.8 (4)	C7—P1—C1	102.21 (16)
C22—C23—H23	120.1	C13—P1—Cu1	113.20 (11)
C24—C23—H23	120.1	C7—P1—Cu1	114.67 (11)
C19—C24—C23	120.7 (4)	C1—P1—Cu1	118.18 (12)
C19—C24—H24	119.6	C19—P2—C25	100.93 (15)
C23—C24—H24	119.6	C19—P2—C31	105.06 (16)
C30—C25—C26	118.2 (4)	C25—P2—C31	103.84 (16)
C30—C25—P2	118.3 (3)	C19—P2—Cu1	117.29 (12)
C26—C25—P2	123.5 (3)	C25—P2—Cu1	117.29 (12)
C27—C26—C25	121.2 (4)	C31—P2—Cu1	110.84 (11)
C27—C26—H26	119.4