Bis{2-[(diisopropyl-phosphan-yl)amino]-pyridine-κN,P}copper(I) hexa-fluorido-phosphate.

The crystal structure of the title compound, [Cu(C(11)H(19)N(2)P)(2)]PF(6), is composed of discrete [Cu(PN-iPr)(2)](+) cations [PN-iPr is 2-(diisopropyl-phosphanyl-amino)-pyridine] and PF(6) (-) anions. The Cu(I) atom is bis-chelated by two independent PN-iPr ligands. It has a distorted tetra-hedral coordination by two P atoms [Cu-P = 2.2277 (4) and 2.2257 (4) Å] and two pyridine N atoms [Cu-N = 2.0763 (11) and 2.0845 (12) Å]. Bond angles about Cu vary from 85.11 (3) (P-Cu-N) to 130.37 (2)° (P-Cu-P). In the crystal, N-H⋯F hydrogen bonds link the Cu complexes and the PF(6) (-) anions into continuous chains, which show a cross-bedded spatial arrangement. In addition, several weaker C-H⋯F inter-actions contribute to the coherence of the structure.

Related literature

For the synthesis and crystal structures of PN-complexes [PN are 2-(phosphanyl­amino)­pyridines], see: Aucott et al. (2000 ▶); Benito-Garagorri, Mereiter & Kirchner (2007 ▶); Standfest-Hauser et al. (2009 ▶). For applications of PN-complexes in catalysis, see: Aguirre et al. (2007 ▶); Benito-Garagorri, Wieder­mann et al. (2007 ▶). For the chemistry and crystal structures of related PNP-complexes [PNP = 2,6-bis­(phos­phanyl­amino)­pyridine], see: Benito-Garagorri et al. (2006 ▶). For crystal structures of other related Cu(I) complexes, see: Hursthouse et al. (2003 ▶); Healy (2008 ▶).

Experimental

Crystal data

[Cu(C11H19N2P)2]PF6

M = 629.01

Monoclinic,

a = 11.0357 (13) Å

b = 9.2129 (11) Å

c = 14.4282 (17) Å

β = 96.723 (1)°

V = 1456.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.97 mm−1

T = 100 K

0.45 × 0.22 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.65, T max = 0.75

21170 measured reflections

8422 independent reflections

8187 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.054

S = 1.02

8422 reflections

334 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.26 e Å−3

Absolute structure: Flack (1983 ▶), 4180 Friedel pairs, merohedral twin with twin proportions refined

Flack parameter: 0.410 (4)

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT, SADABS and XPREP (Bruker, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020283/zs2038sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020283/zs2038Isup2.hkl

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

[Cu(C11H19N2P)2]PF6	F(000) = 652
Mr = 629.01	Dx = 1.434 Mg m−3
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yac	Cell parameters from 9966 reflections
a = 11.0357 (13) Å	θ = 2.5–30.0°
b = 9.2129 (11) Å	µ = 0.97 mm−1
c = 14.4282 (17) Å	T = 100 K
β = 96.723 (1)°	Block, colourless
V = 1456.8 (3) Å3	0.45 × 0.22 × 0.20 mm
Z = 2

Bruker APEXII CCD diffractometer	8422 independent reflections
Radiation source: fine-focus sealed tube	8187 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 30.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→15
Tmin = 0.65, Tmax = 0.75	k = −12→12
21170 measured reflections	l = −20→20

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.021	H-atom parameters constrained
wR(F2) = 0.054	w = 1/[σ2(Fo2) + (0.0327P)2 + 0.1922P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
8422 reflections	Δρmax = 0.35 e Å−3
334 parameters	Δρmin = −0.26 e Å−3
2 restraints	Absolute structure: Flack (1983), 4180 Friedel pairs, merohedral twin with twin proportions refined
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.410 (4)

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

	x	y	z	Uiso*/Ueq
Cu1	0.545130 (11)	0.141471 (15)	0.626623 (10)	0.01477 (4)
P1	0.38719 (3)	0.26283 (4)	0.55383 (2)	0.01685 (6)
P2	0.72626 (3)	0.09024 (3)	0.58123 (2)	0.01465 (6)
N1	0.50957 (10)	0.25486 (12)	0.74483 (8)	0.0155 (2)
N2	0.34515 (12)	0.35253 (13)	0.64884 (8)	0.0209 (2)
H2N	0.2830	0.4129	0.6411	0.025*
N3	0.54844 (10)	−0.07232 (12)	0.67416 (8)	0.0168 (2)
N4	0.74461 (10)	−0.07879 (12)	0.62954 (8)	0.0180 (2)
H4N	0.8145	−0.1241	0.6281	0.022*
C1	0.40583 (12)	0.33308 (14)	0.73755 (9)	0.0164 (2)
C2	0.36015 (13)	0.39407 (15)	0.81595 (10)	0.0198 (2)
H2	0.2852	0.4459	0.8095	0.024*
C3	0.42655 (14)	0.37681 (15)	0.90213 (10)	0.0215 (3)
H3	0.3978	0.4173	0.9560	0.026*
C4	0.53606 (13)	0.29988 (15)	0.91019 (9)	0.0207 (3)
H4	0.5842	0.2893	0.9688	0.025*
C5	0.57229 (12)	0.23970 (14)	0.83056 (9)	0.0178 (2)
H5	0.6455	0.1844	0.8362	0.021*
C6	0.24294 (13)	0.18007 (18)	0.50231 (11)	0.0249 (3)
H6	0.1814	0.2584	0.4860	0.030*
C7	0.26381 (16)	0.0977 (2)	0.41411 (12)	0.0325 (3)
H7A	0.3187	0.0157	0.4304	0.049*
H7B	0.3005	0.1629	0.3715	0.049*
H7C	0.1856	0.0616	0.3836	0.049*
C8	0.19540 (16)	0.0774 (3)	0.57232 (13)	0.0435 (5)
H8A	0.2568	0.0027	0.5906	0.065*
H8B	0.1201	0.0311	0.5439	0.065*
H8C	0.1786	0.1321	0.6276	0.065*
C9	0.41591 (14)	0.40856 (16)	0.47148 (10)	0.0228 (3)
H9	0.4234	0.3609	0.4101	0.027*
C10	0.53711 (19)	0.4818 (2)	0.50186 (15)	0.0423 (4)
H10A	0.5560	0.5500	0.4535	0.063*
H10B	0.6015	0.4082	0.5114	0.063*
H10C	0.5322	0.5344	0.5603	0.063*
C11	0.3130 (2)	0.5190 (3)	0.45456 (15)	0.0473 (5)
H11A	0.3089	0.5764	0.5113	0.071*
H11B	0.2354	0.4682	0.4383	0.071*
H11C	0.3285	0.5835	0.4032	0.071*
C12	0.65306 (12)	−0.14630 (13)	0.67082 (9)	0.0161 (2)
C13	0.67045 (13)	−0.28684 (15)	0.70895 (11)	0.0218 (3)
H13	0.7447	−0.3376	0.7055	0.026*
C14	0.57773 (14)	−0.34880 (15)	0.75124 (12)	0.0269 (3)
H14	0.5874	−0.4432	0.7775	0.032*
C15	0.46883 (14)	−0.27208 (17)	0.75539 (12)	0.0280 (3)
H15	0.4039	−0.3128	0.7846	0.034*
C16	0.45880 (13)	−0.13615 (15)	0.71590 (11)	0.0220 (3)
H16	0.3848	−0.0843	0.7181	0.026*
C17	0.87311 (12)	0.17551 (15)	0.62197 (10)	0.0195 (2)
H17	0.9400	0.1074	0.6099	0.023*
C18	0.88851 (16)	0.31683 (17)	0.56853 (12)	0.0278 (3)
H18A	0.8217	0.3834	0.5778	0.042*
H18B	0.8871	0.2955	0.5019	0.042*
H18C	0.9666	0.3620	0.5918	0.042*
C19	0.88143 (15)	0.20342 (19)	0.72714 (10)	0.0278 (3)
H19A	0.9629	0.2401	0.7497	0.042*
H19B	0.8667	0.1126	0.7594	0.042*
H19C	0.8200	0.2754	0.7396	0.042*
C20	0.73108 (13)	0.05665 (15)	0.45568 (9)	0.0205 (2)
H20	0.7185	0.1517	0.4224	0.025*
C21	0.62513 (16)	−0.0434 (2)	0.41957 (11)	0.0319 (3)
H21A	0.6225	−0.0543	0.3518	0.048*
H21B	0.5482	−0.0012	0.4344	0.048*
H21C	0.6369	−0.1387	0.4494	0.048*
C22	0.85233 (15)	−0.00667 (18)	0.43271 (11)	0.0284 (3)
H22A	0.8741	−0.0907	0.4729	0.043*
H22B	0.9163	0.0672	0.4434	0.043*
H22C	0.8441	−0.0371	0.3672	0.043*
P3	0.55962 (3)	0.31567 (4)	0.21299 (3)	0.01976 (7)
F1	0.62918 (10)	0.43352 (14)	0.15595 (8)	0.0398 (3)
F2	0.48767 (9)	0.20025 (11)	0.26926 (7)	0.0333 (2)
F3	0.46624 (12)	0.28652 (18)	0.12151 (7)	0.0542 (4)
F4	0.65102 (12)	0.34760 (14)	0.30470 (9)	0.0516 (4)
F5	0.64776 (15)	0.19392 (16)	0.18453 (16)	0.0785 (6)
F6	0.47085 (12)	0.43906 (12)	0.24247 (9)	0.0434 (3)

	U11	U22	U33	U12	U13	U23
Cu1	0.01443 (6)	0.01369 (7)	0.01602 (7)	0.00390 (6)	0.00110 (5)	−0.00054 (6)
P1	0.01635 (13)	0.01949 (15)	0.01425 (13)	0.00588 (12)	−0.00017 (11)	−0.00045 (12)
P2	0.01461 (13)	0.01342 (14)	0.01588 (14)	0.00242 (11)	0.00163 (10)	0.00086 (11)
N1	0.0170 (5)	0.0150 (5)	0.0149 (5)	0.0012 (4)	0.0026 (4)	0.0010 (4)
N2	0.0227 (5)	0.0232 (6)	0.0166 (5)	0.0126 (4)	0.0011 (4)	0.0002 (4)
N3	0.0160 (5)	0.0143 (5)	0.0201 (5)	0.0010 (4)	0.0017 (4)	−0.0007 (4)
N4	0.0152 (5)	0.0154 (5)	0.0236 (5)	0.0045 (4)	0.0031 (4)	0.0051 (4)
C1	0.0191 (6)	0.0135 (5)	0.0166 (6)	0.0022 (4)	0.0026 (4)	0.0003 (4)
C2	0.0250 (6)	0.0142 (6)	0.0215 (6)	0.0028 (5)	0.0086 (5)	−0.0007 (5)
C3	0.0300 (7)	0.0174 (6)	0.0184 (6)	−0.0044 (5)	0.0088 (5)	−0.0032 (5)
C4	0.0262 (6)	0.0211 (6)	0.0148 (5)	−0.0068 (5)	0.0019 (5)	0.0010 (5)
C5	0.0181 (5)	0.0168 (6)	0.0181 (6)	−0.0018 (4)	0.0009 (4)	0.0024 (4)
C6	0.0180 (6)	0.0313 (7)	0.0239 (7)	0.0052 (5)	−0.0038 (5)	−0.0009 (6)
C7	0.0363 (8)	0.0344 (8)	0.0256 (7)	−0.0071 (7)	−0.0008 (6)	−0.0060 (6)
C8	0.0217 (7)	0.0752 (15)	0.0336 (9)	−0.0164 (8)	0.0036 (6)	0.0046 (9)
C9	0.0270 (7)	0.0248 (7)	0.0162 (6)	0.0058 (5)	0.0010 (5)	0.0019 (5)
C10	0.0443 (10)	0.0269 (8)	0.0513 (11)	−0.0091 (7)	−0.0123 (8)	0.0144 (8)
C11	0.0472 (11)	0.0484 (12)	0.0475 (11)	0.0239 (9)	0.0106 (9)	0.0275 (9)
C12	0.0150 (5)	0.0146 (5)	0.0182 (6)	0.0005 (4)	0.0000 (4)	−0.0010 (4)
C13	0.0204 (6)	0.0139 (6)	0.0304 (7)	0.0019 (5)	0.0007 (5)	0.0021 (5)
C14	0.0256 (7)	0.0151 (6)	0.0399 (9)	−0.0017 (5)	0.0038 (6)	0.0056 (6)
C15	0.0242 (7)	0.0209 (7)	0.0406 (8)	−0.0029 (5)	0.0105 (6)	0.0057 (6)
C16	0.0175 (6)	0.0200 (6)	0.0290 (7)	0.0006 (5)	0.0056 (5)	0.0007 (5)
C17	0.0178 (6)	0.0192 (6)	0.0216 (6)	−0.0013 (5)	0.0020 (5)	0.0007 (5)
C18	0.0316 (7)	0.0235 (7)	0.0287 (7)	−0.0067 (6)	0.0056 (6)	0.0017 (6)
C19	0.0268 (7)	0.0336 (8)	0.0217 (7)	−0.0065 (6)	−0.0034 (5)	−0.0007 (6)
C20	0.0250 (6)	0.0197 (6)	0.0169 (6)	0.0061 (5)	0.0024 (5)	0.0005 (5)
C21	0.0324 (8)	0.0368 (9)	0.0251 (7)	0.0005 (7)	−0.0024 (6)	−0.0088 (6)
C22	0.0309 (7)	0.0307 (8)	0.0253 (6)	0.0071 (6)	0.0104 (6)	−0.0018 (6)
P3	0.01635 (14)	0.02039 (15)	0.02286 (16)	−0.00373 (12)	0.00365 (12)	−0.00201 (13)
F1	0.0306 (5)	0.0534 (7)	0.0353 (5)	−0.0215 (5)	0.0030 (4)	0.0106 (5)
F2	0.0329 (5)	0.0303 (5)	0.0366 (5)	−0.0113 (4)	0.0039 (4)	0.0085 (4)
F3	0.0530 (7)	0.0899 (10)	0.0193 (4)	−0.0476 (7)	0.0026 (4)	−0.0051 (5)
F4	0.0451 (7)	0.0571 (8)	0.0453 (7)	−0.0261 (6)	−0.0252 (5)	0.0224 (6)
F5	0.0594 (9)	0.0427 (8)	0.1435 (17)	0.0108 (7)	0.0543 (10)	−0.0213 (9)
F6	0.0505 (6)	0.0329 (6)	0.0500 (6)	0.0158 (5)	0.0188 (5)	0.0059 (5)

Cu1—N1	2.0763 (11)	C10—H10A	0.9800
Cu1—N3	2.0845 (12)	C10—H10B	0.9800
Cu1—P2	2.2257 (4)	C10—H10C	0.9800
Cu1—P1	2.2277 (4)	C11—H11A	0.9800
P1—N2	1.7107 (12)	C11—H11B	0.9800
P1—C6	1.8415 (16)	C11—H11C	0.9800
P1—C9	1.8446 (15)	C12—C13	1.4112 (18)
P2—N4	1.7084 (12)	C13—C14	1.375 (2)
P2—C17	1.8347 (14)	C13—H13	0.9500
P2—C20	1.8446 (14)	C14—C15	1.401 (2)
N1—C1	1.3464 (16)	C14—H14	0.9500
N1—C5	1.3521 (16)	C15—C16	1.375 (2)
N2—C1	1.3850 (17)	C15—H15	0.9500
N2—H2N	0.8800	C16—H16	0.9500
N3—C12	1.3464 (16)	C17—C19	1.531 (2)
N3—C16	1.3516 (18)	C17—C18	1.533 (2)
N4—C12	1.3795 (17)	C17—H17	1.0000
N4—H4N	0.8800	C18—H18A	0.9800
C1—C2	1.4080 (18)	C18—H18B	0.9800
C2—C3	1.377 (2)	C18—H18C	0.9800
C2—H2	0.9500	C19—H19A	0.9800
C3—C4	1.394 (2)	C19—H19B	0.9800
C3—H3	0.9500	C19—H19C	0.9800
C4—C5	1.3766 (19)	C20—C22	1.531 (2)
C4—H4	0.9500	C20—C21	1.531 (2)
C5—H5	0.9500	C20—H20	1.0000
C6—C8	1.522 (3)	C21—H21A	0.9800
C6—C7	1.522 (2)	C21—H21B	0.9800
C6—H6	1.0000	C21—H21C	0.9800
C7—H7A	0.9800	C22—H22A	0.9800
C7—H7B	0.9800	C22—H22B	0.9800
C7—H7C	0.9800	C22—H22C	0.9800
C8—H8A	0.9800	P3—F5	1.5704 (13)
C8—H8B	0.9800	P3—F6	1.5907 (11)
C8—H8C	0.9800	P3—F4	1.5944 (12)
C9—C10	1.516 (2)	P3—F3	1.5993 (11)
C9—C11	1.523 (2)	P3—F2	1.6036 (10)
C9—H9	1.0000	P3—F1	1.6103 (11)
N1—Cu1—N3	101.70 (4)	H10B—C10—H10C	109.5
N1—Cu1—P2	127.66 (3)	C9—C11—H11A	109.5
N3—Cu1—P2	85.11 (3)	C9—C11—H11B	109.5
N1—Cu1—P1	85.53 (3)	H11A—C11—H11B	109.5
N3—Cu1—P1	127.73 (3)	C9—C11—H11C	109.5
P2—Cu1—P1	130.374 (15)	H11A—C11—H11C	109.5
N2—P1—C6	102.75 (7)	H11B—C11—H11C	109.5
N2—P1—C9	104.34 (7)	N3—C12—N4	117.49 (12)
C6—P1—C9	104.30 (7)	N3—C12—C13	121.91 (12)
N2—P1—Cu1	97.78 (4)	N4—C12—C13	120.59 (12)
C6—P1—Cu1	125.04 (5)	C14—C13—C12	118.66 (13)
C9—P1—Cu1	119.02 (5)	C14—C13—H13	120.7
N4—P2—C17	101.62 (6)	C12—C13—H13	120.7
N4—P2—C20	103.42 (6)	C13—C14—C15	119.73 (13)
C17—P2—C20	105.10 (6)	C13—C14—H14	120.1
N4—P2—Cu1	98.10 (4)	C15—C14—H14	120.1
C17—P2—Cu1	127.23 (5)	C16—C15—C14	118.00 (13)
C20—P2—Cu1	117.04 (5)	C16—C15—H15	121.0
C1—N1—C5	117.79 (11)	C14—C15—H15	121.0
C1—N1—Cu1	116.49 (9)	N3—C16—C15	123.59 (13)
C5—N1—Cu1	125.01 (9)	N3—C16—H16	118.2
C1—N2—P1	122.07 (9)	C15—C16—H16	118.2
C1—N2—H2N	119.0	C19—C17—C18	111.02 (13)
P1—N2—H2N	119.0	C19—C17—P2	109.74 (10)
C12—N3—C16	118.11 (12)	C18—C17—P2	110.39 (10)
C12—N3—Cu1	116.65 (9)	C19—C17—H17	108.5
C16—N3—Cu1	124.90 (9)	C18—C17—H17	108.5
C12—N4—P2	121.95 (9)	P2—C17—H17	108.5
C12—N4—H4N	119.0	C17—C18—H18A	109.5
P2—N4—H4N	119.0	C17—C18—H18B	109.5
N1—C1—N2	117.13 (12)	H18A—C18—H18B	109.5
N1—C1—C2	122.14 (12)	C17—C18—H18C	109.5
N2—C1—C2	120.73 (12)	H18A—C18—H18C	109.5
C3—C2—C1	118.48 (13)	H18B—C18—H18C	109.5
C3—C2—H2	120.8	C17—C19—H19A	109.5
C1—C2—H2	120.8	C17—C19—H19B	109.5
C2—C3—C4	119.91 (12)	H19A—C19—H19B	109.5
C2—C3—H3	120.0	C17—C19—H19C	109.5
C4—C3—H3	120.0	H19A—C19—H19C	109.5
C5—C4—C3	117.96 (13)	H19B—C19—H19C	109.5
C5—C4—H4	121.0	C22—C20—C21	110.42 (13)
C3—C4—H4	121.0	C22—C20—P2	113.76 (10)
N1—C5—C4	123.66 (13)	C21—C20—P2	109.05 (10)
N1—C5—H5	118.2	C22—C20—H20	107.8
C4—C5—H5	118.2	C21—C20—H20	107.8
C8—C6—C7	110.05 (15)	P2—C20—H20	107.8
C8—C6—P1	109.78 (11)	C20—C21—H21A	109.5
C7—C6—P1	109.61 (11)	C20—C21—H21B	109.5
C8—C6—H6	109.1	H21A—C21—H21B	109.5
C7—C6—H6	109.1	C20—C21—H21C	109.5
P1—C6—H6	109.1	H21A—C21—H21C	109.5
C6—C7—H7A	109.5	H21B—C21—H21C	109.5
C6—C7—H7B	109.5	C20—C22—H22A	109.5
H7A—C7—H7B	109.5	C20—C22—H22B	109.5
C6—C7—H7C	109.5	H22A—C22—H22B	109.5
H7A—C7—H7C	109.5	C20—C22—H22C	109.5
H7B—C7—H7C	109.5	H22A—C22—H22C	109.5
C6—C8—H8A	109.5	H22B—C22—H22C	109.5
C6—C8—H8B	109.5	F5—P3—F6	179.62 (11)
H8A—C8—H8B	109.5	F5—P3—F4	89.87 (10)
C6—C8—H8C	109.5	F6—P3—F4	89.76 (8)
H8A—C8—H8C	109.5	F5—P3—F3	91.33 (10)
H8B—C8—H8C	109.5	F6—P3—F3	89.04 (8)
C10—C9—C11	111.42 (16)	F4—P3—F3	178.79 (9)
C10—C9—P1	110.47 (11)	F5—P3—F2	90.99 (8)
C11—C9—P1	114.10 (12)	F6—P3—F2	88.94 (6)
C10—C9—H9	106.8	F4—P3—F2	90.28 (6)
C11—C9—H9	106.8	F3—P3—F2	89.83 (6)
P1—C9—H9	106.8	F5—P3—F1	90.06 (8)
C9—C10—H10A	109.5	F6—P3—F1	90.01 (7)
C9—C10—H10B	109.5	F4—P3—F1	90.38 (6)
H10A—C10—H10B	109.5	F3—P3—F1	89.49 (6)
C9—C10—H10C	109.5	F2—P3—F1	178.76 (6)
H10A—C10—H10C	109.5
N1—Cu1—P1—N2	−3.58 (6)	N2—C1—C2—C3	−177.28 (13)
N3—Cu1—P1—N2	97.77 (6)	C1—C2—C3—C4	−0.2 (2)
P2—Cu1—P1—N2	−141.14 (5)	C2—C3—C4—C5	−1.8 (2)
N1—Cu1—P1—C6	−115.16 (7)	C1—N1—C5—C4	−0.2 (2)
N3—Cu1—P1—C6	−13.82 (8)	Cu1—N1—C5—C4	−170.10 (10)
P2—Cu1—P1—C6	107.27 (6)	C3—C4—C5—N1	2.1 (2)
N1—Cu1—P1—C9	107.62 (6)	N2—P1—C6—C8	−60.40 (14)
N3—Cu1—P1—C9	−151.03 (7)	C9—P1—C6—C8	−169.05 (13)
P2—Cu1—P1—C9	−29.94 (6)	Cu1—P1—C6—C8	48.75 (14)
N1—Cu1—P2—N4	94.55 (6)	N2—P1—C6—C7	178.60 (11)
N3—Cu1—P2—N4	−6.47 (5)	C9—P1—C6—C7	69.95 (13)
P1—Cu1—P2—N4	−143.64 (4)	Cu1—P1—C6—C7	−72.24 (13)
N1—Cu1—P2—C17	−16.78 (7)	N2—P1—C9—C10	75.95 (13)
N3—Cu1—P2—C17	−117.80 (7)	C6—P1—C9—C10	−176.57 (13)
P1—Cu1—P2—C17	105.03 (6)	Cu1—P1—C9—C10	−31.59 (14)
N1—Cu1—P2—C20	−155.83 (6)	N2—P1—C9—C11	−50.50 (15)
N3—Cu1—P2—C20	103.16 (6)	C6—P1—C9—C11	56.98 (15)
P1—Cu1—P2—C20	−34.02 (6)	Cu1—P1—C9—C11	−158.05 (13)
N3—Cu1—N1—C1	−118.85 (9)	C16—N3—C12—N4	−178.83 (12)
P2—Cu1—N1—C1	148.29 (8)	Cu1—N3—C12—N4	−5.15 (16)
P1—Cu1—N1—C1	8.79 (9)	C16—N3—C12—C13	0.3 (2)
N3—Cu1—N1—C5	51.21 (11)	Cu1—N3—C12—C13	173.97 (10)
P2—Cu1—N1—C5	−41.64 (12)	P2—N4—C12—N3	−1.76 (17)
P1—Cu1—N1—C5	178.85 (11)	P2—N4—C12—C13	179.10 (11)
C6—P1—N2—C1	127.56 (12)	N3—C12—C13—C14	−0.5 (2)
C9—P1—N2—C1	−123.82 (12)	N4—C12—C13—C14	178.60 (14)
Cu1—P1—N2—C1	−1.12 (12)	C12—C13—C14—C15	0.1 (2)
N1—Cu1—N3—C12	−120.07 (10)	C13—C14—C15—C16	0.4 (2)
P2—Cu1—N3—C12	7.42 (9)	C12—N3—C16—C15	0.3 (2)
P1—Cu1—N3—C12	146.52 (8)	Cu1—N3—C16—C15	−172.84 (12)
N1—Cu1—N3—C16	53.13 (12)	C14—C15—C16—N3	−0.6 (3)
P2—Cu1—N3—C16	−179.38 (11)	N4—P2—C17—C19	−70.36 (11)
P1—Cu1—N3—C16	−40.29 (13)	C20—P2—C17—C19	−177.88 (10)
C17—P2—N4—C12	137.45 (11)	Cu1—P2—C17—C19	39.33 (12)
C20—P2—N4—C12	−113.74 (11)	N4—P2—C17—C18	166.96 (10)
Cu1—P2—N4—C12	6.67 (11)	C20—P2—C17—C18	59.45 (12)
C5—N1—C1—N2	177.49 (12)	Cu1—P2—C17—C18	−83.34 (11)
Cu1—N1—C1—N2	−11.70 (15)	N4—P2—C20—C22	−62.05 (12)
C5—N1—C1—C2	−2.08 (19)	C17—P2—C20—C22	44.15 (12)
Cu1—N1—C1—C2	168.72 (10)	Cu1—P2—C20—C22	−168.57 (9)
P1—N2—C1—N1	8.39 (18)	N4—P2—C20—C21	61.68 (11)
P1—N2—C1—C2	−172.03 (11)	C17—P2—C20—C21	167.88 (10)
N1—C1—C2—C3	2.3 (2)	Cu1—P2—C20—C21	−44.84 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···F1i	0.88	2.24	3.1038 (15)	167
N4—H4N···F3ii	0.88	2.26	3.1185 (16)	167
C2—H2···F4i	0.95	2.41	3.306 (2)	158
C20—H20···F4	1.00	2.53	3.502 (2)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯F1i	0.88	2.24	3.1038 (15)	167
N4—H4N⋯F3ii	0.88	2.26	3.1185 (16)	167
C2—H2⋯F4i	0.95	2.41	3.306 (2)	158
C20—H20⋯F4	1.00	2.53	3.502 (2)	164

Symmetry codes: (i) ; (ii) .