Bis(μ-tri­cyano­methanido)­tetrakis­(tri­phenyl­phosphine)­dicopper(I)

Colourless crystals of the title compound, [Cu₂(C₄N₃)₂(C₁₈H₁₅P)₄], were obtained by the reaction of CuC(CN)₃ with excess of molten PPh₃. The crystal structure contains centrosymmetric dimeric units bridged by two C(CN)₃ ligands. The Cu atoms have a distorted tetrahedral coordination.

Key indicators

• Single-crystal X-ray study
• T = 213 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.052
• wR factor = 0.152
• Data-to-parameter ratio = 14.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



RADNW_01  Alert C The radiation wavelength lies outside the expected range
          for the supplied radiation type. Expected range 1.54175-1.54180
          Wavelength given =    1.54184

THETM_01  Alert C The value of sine(theta_max)/wavelength is less than 0.590
          Calculated sin(theta_max)/wavelength =    0.5878

PLAT_213  Alert C Atom  N13    has ADP max/min Ratio ...........       3.10

PLAT_601  Alert C Structure Contains Solvent Accessible VOIDS of      88.00 A   3


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 4 Alert Level C = Please check

---

S1. Comment

The pseudohalide tricyanomethanide C(CN)₃^- is well known as a versatile ligand in coordination compounds. With four available lone electron pairs, its coordination modes vary from unidentate terminal to bi- or tridentate bridging ligand (Golub et al., 1986). Continuing our structural studies on the coordination behaviour of pseudohalides in the system M(PPh₃)_nX, M = Cu(I), Ag(I) or Au(I), we present here the crystal and molecular structure of [Cu(PPh₃)₂C(CN)₃]₂. So far, Au(PPh₃)₂(C(CN)₃) is the only structurally characterized example involving tricyanomethanide within the above-mentioned system (Baukova et al. 1989; Wang & Wang, 1993). The crystal structure of the title compound is built up by centrosymmetric dimeric molecules, in which two copper atoms are asymmetrically bridged end-to-end by two C(CN)₃ ligands, forming a twelve-membered non-planar ring. The distorted tetrahedral coordination at the copper atoms is completed by two triphenylphosphine ligands, showing wide P—Cu—P and small N—Cu—N angles of 124.87 (3)° and 95.92 (12)°, respectively. The Cu—N distances are 2.027 (3) and 2.090 (3) Å. The corresponding Cu—N—C bond angles are 159.6 (3) and 151.7 (3) Å. The C(CN)₃ ligand does not differ significantly from the ideal planar D_{3 h} geometry of non-coordinated tricyanomethanide. The largest deviation from the mean plane is observed for C1 [0.0718 (36) Å]. The bond length C(13)—N(13) of the non-coordinated cyano group is slightly shorter [1.131 (5) Å] compared to the coordinated cyano groups C(12)—N(12) [1.144 (4) Å] and C(11)—N(11) [1.152 (4) Å]. The C—N distances in non-coordinated tricyanomethanide are related to within 1.131–1.139 Å (Potočňák et al., 1997, Potočňák et al., 1998). Selected bond lengths and angles are given in Table 1. Similar end-to-end bridged structures were found for [Ag(PPh₃)₂N(CN)₂]₂ (Bessler et al., 2000) and [Cu(PPh₃)₂N₃]₂ (Ziolo et al., 1971).

S2. Experimental

KC(CN)₃ was prepared according to Trofimenko et al. (1962). CuC(CN)₃ was obtained from KC(CN)₃, CuSO₄ and NaHSO₃ in H₂O solution as a microcrystalline precipitate. [Cu(PPh₃)₂C(CN)₃]₂ was synthesized by the reaction of CuC(CN)₃ in molten PPh₃ at 373 K. The excess PPh₃ was removed with n-hexane and the residue was submitted to continuous extraction with CH₂Cl₂, from which the title compound was obtained in high yield as colourless crystal plates, m.p. 225 °C. Elem. anal. (calc. for C₄₀H₂₀CuN₃P₂/found) C=70.84/70.63 H=4.46/4.15 N=6.20/6.15%.

S3. Refinement

The terminal nitrogen atom N13 presents greater displacement parameters due to its thermal movements. No improvement of the structure factors can be achieved by splitting it into two positions. The H atoms were placed in calculated positions (C—H = 0.94 Å) and allowed to ride with isotropic displacement parameters 20% larger than those of the attached C atom.

Computing details

Data collection: CAD-4 EXPRESS (Enraf-Nonius 1994); cell refinement: CAD-4 EXPRESS; data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1997), ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures

Fig. 1. A view of the title compound. Displacement ellipsoids are drawn at the 30% probability level.

Tetrakis(triphenylphosphine)-bis(µ-tricyanomethanido)dicopper(I)

Crystal data

C80H60Cu2N6P4	Z = 1
Mr = 1356.30	F(000) = 700
Triclinic, P1	Dx = 1.295 Mg m^−3
a = 12.113 (3) Å	Cu Kα radiation, λ = 1.54184 Å
b = 12.8530 (16) Å	Cell parameters from 25 reflections
c = 13.0084 (14) Å	θ = 29.9–50.2°
α = 85.113 (11)°	µ = 2.00 mm^−1
β = 69.290 (12)°	T = 213 K
γ = 66.945 (13)°	Block, colourless
V = 1739.7 (5) Å^3	0.50 × 0.20 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	5634 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.077
Graphite monochromator	θmax = 65.0°, θmin = 5.1°
ω scans	h = −1→14
Absorption correction: ψ scan (Spek, 1997)	k = −14→15
Tmin = 0.634, Tmax = 0.817	l = −14→15
6696 measured reflections	3 standard reflections every 400 reflections
5840 independent reflections	intensity decay: 2.2%

Refinement

Refinement on F^2	Primary atom site location: heavy atom method
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.152	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0797P)^2 + 2.1459P], where P = (Fo^2 + 2Fc^2)/3
5840 reflections	(Δ/σ)max = 0.001
415 parameters	Δρmax = 0.64 e Å^−3
0 restraints	Δρmin = −0.87 e Å^−3

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

6.7218 (0.0162) x + 9.0625 (0.0100) y - 5.6328 (0.0133) z = 6.2981 (0.0239)

* -0.0718 (0.0036) C1 * -0.0236 (0.0028) C11 * 0.0435 (0.0021) N11 * -0.0175 (0.0028) C12_$1 * 0.0397 (0.0021) N12_$1 * -0.0084 (0.0051) C13 * 0.0380 (0.0037) N13

Rms deviation of fitted atoms = 0.0396

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
Cu	0.60412 (4)	0.83892 (3)	0.76120 (4)	0.03351 (16)
P1	0.58828 (7)	0.68705 (6)	0.70137 (6)	0.03146 (19)
C111	0.5807 (3)	0.6871 (2)	0.5642 (3)	0.0343 (6)
C112	0.6544 (3)	0.7333 (3)	0.4813 (3)	0.0442 (8)
H112	0.7073	0.7622	0.4972	0.053*
C113	0.6509 (4)	0.7373 (3)	0.3760 (3)	0.0546 (9)
H113	0.7031	0.7667	0.3203	0.066*
C114	0.5709 (4)	0.6983 (4)	0.3528 (3)	0.0577 (10)
H114	0.5667	0.7032	0.2817	0.069*
C115	0.4973 (4)	0.6522 (4)	0.4332 (3)	0.0585 (10)
H115	0.4434	0.6248	0.4171	0.070*
C116	0.5029 (3)	0.6464 (3)	0.5383 (3)	0.0460 (8)
H116	0.4530	0.6143	0.5929	0.055*
C121	0.7287 (3)	0.5602 (2)	0.6962 (3)	0.0342 (6)
C122	0.7535 (3)	0.5299 (3)	0.7945 (3)	0.0419 (7)
H122	0.6928	0.5684	0.8617	0.050*
C123	0.8670 (3)	0.4438 (3)	0.7925 (3)	0.0494 (8)
H123	0.8827	0.4233	0.8587	0.059*
C124	0.9577 (3)	0.3874 (3)	0.6944 (3)	0.0506 (9)
H124	1.0359	0.3305	0.6935	0.061*
C125	0.9332 (3)	0.4148 (3)	0.5980 (3)	0.0500 (9)
H125	0.9941	0.3751	0.5314	0.060*
C126	0.8193 (3)	0.5006 (3)	0.5986 (3)	0.0414 (7)
H126	0.8033	0.5185	0.5323	0.050*
C131	0.4531 (3)	0.6525 (3)	0.7881 (3)	0.0385 (7)
C132	0.4607 (4)	0.5427 (3)	0.8057 (3)	0.0539 (9)
H132	0.5395	0.4816	0.7751	0.065*
C133	0.3524 (5)	0.5219 (4)	0.8685 (4)	0.0710 (12)
H133	0.3591	0.4470	0.8815	0.085*
C134	0.2372 (4)	0.6091 (5)	0.9110 (4)	0.0747 (14)
H134	0.1637	0.5943	0.9502	0.090*
C135	0.2280 (4)	0.7189 (5)	0.8967 (4)	0.0706 (13)
H135	0.1488	0.7793	0.9284	0.085*
C136	0.3365 (3)	0.7413 (3)	0.8349 (3)	0.0518 (9)
H136	0.3300	0.8165	0.8251	0.062*
P2	0.75909 (7)	0.90759 (6)	0.67023 (7)	0.0347 (2)
C211	0.7348 (3)	1.0422 (3)	0.7297 (3)	0.0397 (7)
C212	0.7600 (3)	1.1285 (3)	0.6678 (3)	0.0466 (8)
H212	0.7886	1.1207	0.5906	0.056*
C213	0.7432 (3)	1.2268 (3)	0.7192 (4)	0.0532 (9)
H213	0.7608	1.2849	0.6764	0.064*
C214	0.7013 (4)	1.2398 (3)	0.8317 (4)	0.0580 (10)
H214	0.6930	1.3054	0.8658	0.070*
C215	0.6717 (5)	1.1572 (4)	0.8940 (4)	0.0716 (13)
H215	0.6405	1.1668	0.9712	0.086*
C216	0.6878 (5)	1.0590 (3)	0.8433 (3)	0.0625 (11)
H216	0.6663	1.0028	0.8869	0.075*
C221	0.7772 (3)	0.9362 (2)	0.5271 (3)	0.0360 (7)
C222	0.6668 (3)	1.0022 (3)	0.5038 (3)	0.0449 (8)
H222	0.5881	1.0336	0.5619	0.054*
C223	0.6717 (3)	1.0219 (3)	0.3961 (3)	0.0501 (8)
H223	0.5968	1.0666	0.3815	0.060*
C224	0.7867 (4)	0.9757 (3)	0.3103 (3)	0.0506 (8)
H224	0.7901	0.9887	0.2372	0.061*
C225	0.8964 (3)	0.9108 (3)	0.3316 (3)	0.0494 (8)
H225	0.9747	0.8797	0.2730	0.059*
C226	0.8922 (3)	0.8911 (3)	0.4393 (3)	0.0400 (7)
H226	0.9678	0.8468	0.4530	0.048*
C231	0.9191 (3)	0.8142 (3)	0.6677 (3)	0.0376 (7)
C232	0.9412 (3)	0.7033 (3)	0.6938 (3)	0.0435 (8)
H232	0.8738	0.6779	0.7132	0.052*
C233	1.0612 (3)	0.6288 (3)	0.6919 (3)	0.0522 (9)
H233	1.0748	0.5535	0.7103	0.063*
C234	1.1602 (3)	0.6648 (3)	0.6632 (3)	0.0543 (9)
H234	1.2420	0.6141	0.6609	0.065*
C235	1.1396 (3)	0.7753 (3)	0.6377 (4)	0.0565 (10)
H235	1.2073	0.8001	0.6187	0.068*
C236	1.0201 (3)	0.8502 (3)	0.6397 (3)	0.0483 (8)
H236	1.0069	0.9256	0.6222	0.058*
N11	0.6341 (3)	0.7953 (2)	0.9104 (3)	0.0473 (7)
C11	0.6654 (3)	0.8083 (3)	0.9807 (3)	0.0394 (7)
C1	0.6998 (3)	0.8307 (3)	1.0662 (3)	0.0429 (8)
C12	0.3782 (3)	1.0665 (3)	0.8710 (3)	0.0390 (7)
N12	0.4446 (3)	0.9811 (2)	0.8231 (3)	0.0460 (7)
C13	0.8154 (4)	0.7602 (4)	1.0795 (3)	0.0689 (13)
N13	0.9080 (4)	0.7044 (5)	1.0921 (4)	0.131 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu	0.0286 (2)	0.0285 (2)	0.0391 (3)	−0.01020 (18)	−0.00621 (19)	−0.00496 (18)
P1	0.0264 (4)	0.0273 (4)	0.0366 (4)	−0.0104 (3)	−0.0053 (3)	−0.0033 (3)
C111	0.0293 (14)	0.0272 (14)	0.0397 (17)	−0.0067 (11)	−0.0080 (12)	−0.0035 (12)
C112	0.0475 (18)	0.0470 (18)	0.0426 (19)	−0.0270 (15)	−0.0110 (15)	0.0027 (14)
C113	0.066 (2)	0.056 (2)	0.042 (2)	−0.0306 (19)	−0.0114 (17)	0.0041 (16)
C114	0.071 (3)	0.061 (2)	0.044 (2)	−0.025 (2)	−0.0232 (19)	0.0008 (17)
C115	0.064 (2)	0.070 (3)	0.061 (2)	−0.036 (2)	−0.033 (2)	0.004 (2)
C116	0.0425 (17)	0.0513 (19)	0.050 (2)	−0.0246 (15)	−0.0151 (15)	0.0026 (16)
C121	0.0303 (14)	0.0267 (14)	0.0425 (17)	−0.0120 (12)	−0.0073 (12)	−0.0013 (12)
C122	0.0410 (17)	0.0358 (16)	0.0436 (19)	−0.0128 (14)	−0.0107 (14)	0.0010 (14)
C123	0.052 (2)	0.0392 (18)	0.061 (2)	−0.0169 (16)	−0.0262 (18)	0.0103 (16)
C124	0.0367 (17)	0.0334 (17)	0.074 (3)	−0.0083 (14)	−0.0166 (17)	0.0067 (16)
C125	0.0379 (17)	0.0352 (17)	0.059 (2)	−0.0056 (14)	−0.0045 (15)	−0.0038 (15)
C126	0.0389 (17)	0.0338 (16)	0.0432 (18)	−0.0118 (13)	−0.0066 (14)	−0.0018 (13)
C131	0.0343 (15)	0.0438 (17)	0.0357 (17)	−0.0180 (13)	−0.0059 (13)	−0.0030 (13)
C132	0.052 (2)	0.053 (2)	0.054 (2)	−0.0297 (17)	−0.0050 (17)	0.0018 (17)
C133	0.081 (3)	0.084 (3)	0.061 (3)	−0.061 (3)	−0.011 (2)	0.016 (2)
C134	0.063 (3)	0.126 (4)	0.046 (2)	−0.062 (3)	−0.0007 (19)	0.001 (2)
C135	0.0362 (19)	0.103 (4)	0.058 (3)	−0.026 (2)	0.0040 (17)	−0.014 (2)
C136	0.0348 (17)	0.061 (2)	0.048 (2)	−0.0157 (16)	−0.0015 (15)	−0.0057 (17)
P2	0.0307 (4)	0.0296 (4)	0.0421 (5)	−0.0141 (3)	−0.0074 (3)	−0.0011 (3)
C211	0.0368 (16)	0.0312 (15)	0.051 (2)	−0.0171 (13)	−0.0098 (14)	−0.0030 (13)
C212	0.0443 (18)	0.0385 (17)	0.053 (2)	−0.0176 (15)	−0.0100 (15)	0.0010 (15)
C213	0.051 (2)	0.0303 (16)	0.078 (3)	−0.0188 (15)	−0.0185 (19)	0.0033 (16)
C214	0.058 (2)	0.043 (2)	0.075 (3)	−0.0256 (17)	−0.014 (2)	−0.0123 (18)
C215	0.104 (4)	0.066 (3)	0.054 (2)	−0.055 (3)	−0.013 (2)	−0.007 (2)
C216	0.097 (3)	0.054 (2)	0.049 (2)	−0.050 (2)	−0.016 (2)	0.0028 (18)
C221	0.0350 (15)	0.0290 (14)	0.0445 (18)	−0.0145 (12)	−0.0118 (13)	−0.0008 (12)
C222	0.0355 (16)	0.0381 (17)	0.056 (2)	−0.0113 (14)	−0.0119 (15)	−0.0014 (15)
C223	0.049 (2)	0.0425 (18)	0.062 (2)	−0.0141 (15)	−0.0274 (18)	0.0074 (16)
C224	0.061 (2)	0.0440 (19)	0.050 (2)	−0.0213 (17)	−0.0222 (17)	0.0048 (16)
C225	0.0464 (19)	0.0454 (19)	0.046 (2)	−0.0150 (15)	−0.0063 (15)	−0.0014 (15)
C226	0.0373 (16)	0.0351 (16)	0.0432 (18)	−0.0118 (13)	−0.0112 (13)	0.0020 (13)
C231	0.0327 (15)	0.0384 (16)	0.0428 (18)	−0.0171 (13)	−0.0098 (13)	−0.0013 (13)
C232	0.0374 (16)	0.0395 (17)	0.056 (2)	−0.0197 (14)	−0.0136 (15)	0.0047 (15)
C233	0.0427 (18)	0.0401 (18)	0.075 (3)	−0.0164 (15)	−0.0222 (18)	0.0069 (17)
C234	0.0354 (17)	0.055 (2)	0.070 (3)	−0.0131 (16)	−0.0200 (17)	0.0042 (18)
C235	0.0401 (19)	0.062 (2)	0.076 (3)	−0.0292 (18)	−0.0208 (18)	0.010 (2)
C236	0.0422 (18)	0.0444 (18)	0.065 (2)	−0.0255 (15)	−0.0189 (16)	0.0110 (16)
N11	0.0451 (16)	0.0401 (15)	0.0482 (18)	−0.0112 (12)	−0.0104 (13)	−0.0072 (13)
C11	0.0384 (16)	0.0272 (15)	0.0414 (18)	−0.0058 (12)	−0.0076 (14)	−0.0039 (13)
C1	0.0364 (16)	0.0362 (17)	0.0427 (19)	0.0011 (13)	−0.0134 (14)	−0.0075 (14)
C12	0.0307 (15)	0.0387 (17)	0.0423 (18)	−0.0066 (14)	−0.0129 (13)	−0.0044 (14)
N12	0.0368 (14)	0.0417 (16)	0.0525 (17)	−0.0055 (13)	−0.0155 (13)	−0.0110 (13)
C13	0.054 (2)	0.071 (3)	0.048 (2)	0.014 (2)	−0.0178 (18)	−0.018 (2)
N13	0.071 (3)	0.157 (5)	0.086 (3)	0.057 (3)	−0.043 (3)	−0.036 (3)

Geometric parameters (Å, º)

Cu—N12	2.027 (3)	P2—C211	1.829 (3)
Cu—N11	2.090 (3)	C211—C212	1.382 (5)
Cu—P1	2.2607 (8)	C211—C216	1.385 (5)
Cu—P2	2.2916 (9)	C212—C213	1.390 (5)
P1—C111	1.818 (3)	C213—C214	1.370 (6)
P1—C121	1.823 (3)	C214—C215	1.363 (6)
P1—C131	1.825 (3)	C215—C216	1.387 (5)
C111—C116	1.384 (4)	C221—C226	1.392 (4)
C111—C112	1.393 (4)	C221—C222	1.398 (5)
C112—C113	1.380 (5)	C222—C223	1.386 (5)
C113—C114	1.377 (6)	C223—C224	1.380 (5)
C114—C115	1.375 (6)	C224—C225	1.376 (5)
C115—C116	1.387 (5)	C225—C226	1.389 (5)
C121—C126	1.388 (4)	C231—C232	1.379 (5)
C121—C122	1.404 (5)	C231—C236	1.394 (4)
C122—C123	1.380 (5)	C232—C233	1.386 (5)
C123—C124	1.379 (5)	C233—C234	1.372 (5)
C124—C125	1.375 (6)	C234—C235	1.375 (6)
C125—C126	1.387 (5)	C235—C236	1.381 (5)
C131—C132	1.383 (5)	N11—C11	1.152 (4)
C131—C136	1.384 (5)	C11—C1	1.404 (5)
C132—C133	1.392 (5)	C1—C13	1.402 (5)
C133—C134	1.358 (7)	C1—C12^i	1.402 (4)
C134—C135	1.373 (7)	C12—N12	1.144 (4)
C135—C136	1.401 (6)	C12—C1^i	1.402 (4)
P2—C221	1.819 (3)	C13—N13	1.131 (5)
P2—C231	1.827 (3)
N12—Cu—N11	95.92 (12)	C221—P2—C211	103.19 (15)
N12—Cu—P1	119.59 (9)	C231—P2—C211	103.35 (14)
N11—Cu—P1	105.21 (8)	C221—P2—Cu	115.29 (10)
N12—Cu—P2	103.34 (9)	C231—P2—Cu	113.82 (11)
N11—Cu—P2	102.77 (9)	C211—P2—Cu	114.67 (11)
P1—Cu—P2	124.87 (3)	C212—C211—C216	118.0 (3)
C111—P1—C121	104.00 (14)	C212—C211—P2	123.8 (3)
C111—P1—C131	103.67 (14)	C216—C211—P2	118.2 (3)
C121—P1—C131	104.33 (14)	C211—C212—C213	120.3 (4)
C111—P1—Cu	117.82 (10)	C214—C213—C212	120.6 (4)
C121—P1—Cu	109.67 (10)	C215—C214—C213	119.7 (4)
C131—P1—Cu	115.93 (11)	C214—C215—C216	119.9 (4)
C116—C111—C112	118.0 (3)	C211—C216—C215	121.3 (4)
C116—C111—P1	123.6 (3)	C226—C221—C222	118.2 (3)
C112—C111—P1	118.4 (2)	C226—C221—P2	124.1 (2)
C113—C112—C111	121.0 (3)	C222—C221—P2	117.6 (2)
C114—C113—C112	119.9 (3)	C223—C222—C221	120.9 (3)
C115—C114—C113	120.3 (4)	C224—C223—C222	119.9 (3)
C114—C115—C116	119.6 (3)	C225—C224—C223	120.0 (4)
C111—C116—C115	121.3 (3)	C224—C225—C226	120.4 (3)
C126—C121—C122	118.6 (3)	C225—C226—C221	120.6 (3)
C126—C121—P1	123.1 (3)	C232—C231—C236	118.6 (3)
C122—C121—P1	117.9 (2)	C232—C231—P2	118.7 (2)
C123—C122—C121	120.0 (3)	C236—C231—P2	122.7 (3)
C124—C123—C122	120.6 (4)	C231—C232—C233	120.9 (3)
C125—C124—C123	119.8 (3)	C234—C233—C232	120.0 (3)
C124—C125—C126	120.3 (3)	C233—C234—C235	119.8 (3)
C125—C126—C121	120.6 (3)	C234—C235—C236	120.5 (3)
C132—C131—C136	118.9 (3)	C235—C236—C231	120.2 (3)
C132—C131—P1	123.3 (3)	C11—N11—Cu	151.7 (3)
C136—C131—P1	117.8 (3)	N11—C11—C1	176.8 (3)
C131—C132—C133	120.5 (4)	C13—C1—C12^i	121.1 (3)
C134—C133—C132	120.5 (4)	C13—C1—C11	121.3 (3)
C133—C134—C135	120.0 (4)	C12^i—C1—C11	117.2 (3)
C134—C135—C136	120.1 (4)	N12—C12—C1^i	176.9 (3)
C131—C136—C135	120.0 (4)	C12—N12—Cu	159.6 (3)
C221—P2—C231	105.14 (14)	N13—C13—C1	178.7 (5)

Symmetry code: (i) −x+1, −y+2, −z+2.