Acetato­(methanol)[N-phenyl-N,N-bis(2-pyridyl­methyl)­amine]copper(II) hexa­fluoro­phosphate

The title copper complex, [Cu(C₂H₃O₂)(CH₄O)(C₁₈H₁₇N₃)]PF₆, of the tridentate ligand N-phenyl-N,N-bis(2-pyridyl­methyl)­amine (phbpa), displays a distorted octahedral coord­ination geometry in which the κ²O,O′-acetate ligand approaches a κO-binding arrangement. One O atom of the acetate group also accepts an O—H...O hydrogen bond [O...O = 2.654 (2) Å] from a coordinated methanol mol­ecule in a neighbouring complex.

Key indicators

• Single-crystal X-ray study
• T = 180 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in solvent or counterion
• R factor = 0.040
• wR factor = 0.120
• Data-to-parameter ratio = 20.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT221_ALERT_4_B Large Solvent/Anion  F     Ueq(max)/Ueq(min) ...       4.93 Ratio

Alert level C
PLAT216_ALERT_3_C Disordered F23A    (An/Solv) ADP max/min Ratio         5.10
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O2
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        F22
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for       F22A
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for       F23A
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         P2
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        F21
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for       F21A
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         P1
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.09
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      30.00 Perc.
PLAT413_ALERT_2_C Short Inter XH3 .. XHn     H3A    ..  H21A    ..       2.14 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  12 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
   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
   9 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: APEX2 (Bruker–Nonius, 2004); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Acetato(methanol)[N-phenyl-N,N-bis(2-pyridylmethyl)amine]copper(II) hexafluorophosphate

Crystal data

[Cu(C2H3O2)(CH4O)(C18H17N3)]PF6	F(000) = 2344
Mr = 574.94	Dx = 1.625 Mg m^−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 6956 reflections
a = 18.8196 (7) Å	θ = 2.9–27.3°
b = 18.4938 (8) Å	µ = 1.07 mm^−1
c = 13.5023 (6) Å	T = 180 K
V = 4699.4 (3) Å^3	Block, blue-green
Z = 8	0.22 × 0.16 × 0.14 mm

Data collection

Bruker–Nonius X8APEX-II CCD diffractometer	7042 independent reflections
Radiation source: fine-focus sealed tube	5365 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
thin–slice ω and φ scans	θmax = 30.4°, θmin = 3.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −26→26
Tmin = 0.759, Tmax = 0.864	k = −26→26
76538 measured reflections	l = −17→19

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0551P)^2 + 4.6723P] where P = (Fo^2 + 2Fc^2)/3
7042 reflections	(Δ/σ)max = 0.001
346 parameters	Δρmax = 0.75 e Å^−3
28 restraints	Δρmin = −0.45 e Å^−3

Special details

Experimental. INTENSITY STATISTICS FOR DATASET # 1 cm0506m.hkl

Resolution #Data #Theory %Complete Redundancy Mean I Mean I/s R(int) R(sigma)

Inf - 2.00 397 398 99.7 23.44 477.5 87.24 0.0214 0.0088 2.00 - 1.55 404 404 100.0 24.33 200.1 84.88 0.0271 0.0082 1.55 - 1.30 528 528 100.0 20.53 129.9 63.01 0.0328 0.0101 1.30 - 1.15 547 547 100.0 15.35 96.9 48.49 0.0377 0.0134 1.15 - 1.05 559 559 100.0 12.82 62.3 36.73 0.0497 0.0182 1.05 - 0.95 820 820 100.0 10.97 44.4 27.51 0.0646 0.0258 0.95 - 0.90 540 540 100.0 9.76 32.5 20.53 0.0842 0.0362 0.90 - 0.85 684 684 100.0 7.59 27.2 15.60 0.0919 0.0507 0.85 - 0.80 855 855 100.0 6.11 20.7 10.88 0.1207 0.0773 0.80 - 0.75 1105 1105 100.0 5.38 13.8 6.91 0.1701 0.1317 0.75 - 0.70 1303 1326 98.3 4.31 10.6 4.36 0.2255 0.2211 —————————————————————————— 0.80 - 0.70 2408 2431 99.1 4.79 12.1 5.53 0.1933 0.1742 Inf - 0.70 7742 7766 99.7 10.54 70.5 27.92 0.0347 0.0244

Merged [A], lowest resolution = 18.82 Angstroms, 3295 outliers downweighted

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)

3.3600(0.0180) x + 7.7464(0.0107) y + 12.0214(0.0044) z = 10.6187(0.0021)

* -0.0820 (0.0005) N1 * 0.0153 (0.0001) N2 * -0.0820 (0.0005) N3 * 0.1486 (0.0008) Cu1 0.8622 (0.0028) O1

Rms deviation of fitted atoms = 0.0946

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)
Cu1	0.228630 (13)	0.220884 (13)	0.689441 (18)	0.02219 (8)
O1	0.32989 (8)	0.23868 (9)	0.70903 (11)	0.0295 (3)
O2	0.28671 (10)	0.26534 (12)	0.85525 (14)	0.0473 (5)
O3	0.21641 (10)	0.17094 (9)	0.53132 (12)	0.0357 (4)
H3	0.2156	0.1958	0.4793	0.043*
N1	0.22531 (9)	0.12025 (10)	0.73603 (13)	0.0242 (3)
N2	0.11900 (9)	0.21716 (9)	0.71139 (13)	0.0232 (3)
N3	0.20735 (9)	0.31095 (9)	0.61817 (13)	0.0241 (3)
C1	0.28185 (12)	0.07809 (12)	0.75484 (17)	0.0298 (4)
H1A	0.3278	0.0993	0.7578	0.036*
C2	0.27458 (14)	0.00454 (13)	0.76992 (18)	0.0346 (5)
H2A	0.3151	−0.0247	0.7822	0.042*
C3	0.20773 (15)	−0.02584 (12)	0.76694 (17)	0.0352 (5)
H3A	0.2019	−0.0763	0.7776	0.042*
C4	0.14939 (14)	0.01722 (12)	0.74842 (18)	0.0333 (5)
H4A	0.1029	−0.0028	0.7472	0.040*
C5	0.16016 (11)	0.09051 (11)	0.73159 (15)	0.0258 (4)
C6	0.10084 (11)	0.13957 (12)	0.69903 (17)	0.0286 (4)
H6A	0.0899	0.1300	0.6285	0.034*
H6B	0.0577	0.1285	0.7382	0.034*
C7	0.08784 (11)	0.26247 (12)	0.63134 (17)	0.0291 (4)
H7A	0.0438	0.2856	0.6561	0.035*
H7B	0.0748	0.2311	0.5748	0.035*
C8	0.13842 (11)	0.32047 (12)	0.59587 (15)	0.0266 (4)
C9	0.11604 (13)	0.37790 (13)	0.53854 (18)	0.0359 (5)
H9A	0.0670	0.3848	0.5250	0.043*
C10	0.16611 (15)	0.42506 (14)	0.5013 (2)	0.0406 (6)
H10A	0.1517	0.4653	0.4624	0.049*
C11	0.23721 (14)	0.41361 (13)	0.52074 (19)	0.0360 (5)
H11A	0.2725	0.4445	0.4935	0.043*
C12	0.25592 (12)	0.35643 (12)	0.58044 (17)	0.0287 (4)
H12A	0.3047	0.3489	0.5954	0.034*
C13	0.10495 (11)	0.24522 (12)	0.81052 (15)	0.0257 (4)
C14	0.09961 (12)	0.31966 (13)	0.82562 (19)	0.0336 (5)
H14A	0.1047	0.3519	0.7713	0.040*
C15	0.08694 (13)	0.34646 (15)	0.9197 (2)	0.0425 (6)
H15A	0.0832	0.3972	0.9293	0.051*
C16	0.07959 (14)	0.30058 (18)	0.9998 (2)	0.0470 (7)
H16A	0.0716	0.3194	1.0643	0.056*
C17	0.08414 (15)	0.22680 (17)	0.98440 (19)	0.0448 (7)
H17A	0.0785	0.1948	1.0388	0.054*
C18	0.09683 (13)	0.19882 (14)	0.89095 (17)	0.0353 (5)
H18A	0.1000	0.1480	0.8817	0.042*
C19	0.33694 (12)	0.25935 (13)	0.79738 (17)	0.0297 (4)
C20	0.41227 (15)	0.27580 (19)	0.8310 (2)	0.0528 (8)
H20A	0.4116	0.2915	0.9003	0.079*
H20B	0.4323	0.3143	0.7896	0.079*
H20C	0.4415	0.2322	0.8248	0.079*
C21	0.23387 (17)	0.09987 (15)	0.5018 (2)	0.0468 (7)
H21A	0.2230	0.0937	0.4313	0.070*
H21B	0.2061	0.0652	0.5407	0.070*
H21C	0.2846	0.0913	0.5130	0.070*
P1	0.0000	0.0000	0.5000	0.0399 (2)
F11	−0.00632 (11)	0.02300 (11)	0.61348 (14)	0.0648 (5)
F12	0.03713 (12)	0.07509 (11)	0.47708 (16)	0.0725 (6)
F13	−0.07590 (10)	0.03442 (12)	0.47948 (17)	0.0741 (6)
P2	0.5000	0.03687 (5)	0.7500	0.0414 (2)
F21	0.44762 (19)	0.0344 (2)	0.8394 (3)	0.0619 (11)	0.50
F22	0.4539 (3)	0.0948 (3)	0.7015 (4)	0.172 (5)	0.50
F23	0.5464 (2)	−0.0239 (3)	0.7984 (4)	0.131 (3)	0.50
F21A	0.4442 (2)	0.0392 (3)	0.6653 (4)	0.0879 (16)	0.50
F22A	0.4556 (3)	0.0974 (4)	0.8015 (5)	0.192 (6)	0.50
F23A	0.4560 (3)	−0.0191 (4)	0.8028 (5)	0.305 (11)	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.02045 (12)	0.02356 (13)	0.02255 (13)	0.00048 (9)	−0.00061 (9)	0.00122 (9)
O1	0.0228 (7)	0.0400 (9)	0.0256 (7)	−0.0009 (6)	0.0002 (6)	0.0002 (6)
O2	0.0365 (10)	0.0720 (14)	0.0335 (10)	−0.0044 (9)	0.0025 (8)	−0.0207 (9)
O3	0.0565 (11)	0.0290 (8)	0.0217 (7)	0.0049 (7)	0.0001 (7)	−0.0005 (6)
N1	0.0271 (8)	0.0261 (8)	0.0194 (8)	0.0013 (7)	0.0011 (6)	0.0006 (6)
N2	0.0218 (8)	0.0256 (8)	0.0223 (8)	0.0001 (6)	0.0004 (6)	0.0018 (7)
N3	0.0261 (8)	0.0237 (8)	0.0226 (8)	0.0003 (7)	0.0012 (7)	0.0006 (7)
C1	0.0321 (11)	0.0326 (11)	0.0247 (10)	0.0048 (9)	−0.0021 (8)	0.0017 (9)
C2	0.0459 (13)	0.0293 (11)	0.0286 (12)	0.0109 (10)	−0.0027 (10)	0.0025 (9)
C3	0.0549 (15)	0.0239 (10)	0.0268 (11)	0.0025 (10)	−0.0005 (10)	0.0015 (8)
C4	0.0392 (12)	0.0292 (11)	0.0316 (11)	−0.0055 (9)	0.0022 (10)	0.0005 (9)
C5	0.0282 (10)	0.0263 (10)	0.0228 (10)	0.0010 (8)	0.0027 (8)	−0.0010 (8)
C6	0.0238 (9)	0.0284 (10)	0.0336 (11)	−0.0023 (8)	−0.0021 (8)	−0.0014 (9)
C7	0.0242 (10)	0.0361 (11)	0.0269 (10)	0.0007 (8)	−0.0047 (8)	0.0065 (9)
C8	0.0277 (10)	0.0295 (10)	0.0227 (10)	0.0016 (8)	−0.0001 (8)	0.0014 (8)
C9	0.0345 (12)	0.0382 (12)	0.0351 (12)	0.0074 (10)	−0.0012 (10)	0.0079 (10)
C10	0.0498 (15)	0.0329 (12)	0.0390 (13)	0.0065 (11)	0.0009 (11)	0.0122 (10)
C11	0.0440 (14)	0.0279 (11)	0.0360 (12)	−0.0038 (10)	0.0088 (10)	0.0041 (9)
C12	0.0285 (10)	0.0273 (10)	0.0302 (11)	−0.0012 (8)	0.0042 (9)	−0.0002 (9)
C13	0.0194 (9)	0.0334 (10)	0.0244 (10)	0.0024 (8)	−0.0003 (7)	−0.0016 (8)
C14	0.0302 (11)	0.0331 (11)	0.0375 (12)	−0.0047 (9)	0.0068 (9)	−0.0059 (10)
C15	0.0328 (12)	0.0454 (14)	0.0494 (15)	−0.0058 (10)	0.0048 (11)	−0.0196 (12)
C16	0.0327 (12)	0.078 (2)	0.0303 (12)	0.0083 (13)	−0.0027 (10)	−0.0151 (13)
C17	0.0411 (14)	0.0683 (19)	0.0249 (11)	0.0217 (13)	0.0008 (10)	0.0079 (11)
C18	0.0338 (12)	0.0424 (13)	0.0298 (11)	0.0133 (10)	0.0046 (9)	0.0061 (10)
C19	0.0285 (10)	0.0314 (10)	0.0292 (11)	−0.0021 (9)	−0.0010 (8)	−0.0038 (9)
C20	0.0334 (13)	0.078 (2)	0.0474 (16)	−0.0100 (13)	−0.0080 (12)	−0.0111 (15)
C21	0.071 (2)	0.0369 (13)	0.0325 (13)	0.0073 (13)	0.0066 (13)	−0.0076 (11)
P1	0.0362 (5)	0.0452 (5)	0.0383 (5)	−0.0130 (4)	0.0040 (4)	−0.0135 (4)
F11	0.0691 (12)	0.0828 (14)	0.0425 (9)	−0.0209 (10)	0.0092 (8)	−0.0210 (9)
F12	0.0877 (15)	0.0640 (12)	0.0658 (12)	−0.0387 (11)	0.0046 (11)	−0.0010 (10)
F13	0.0510 (11)	0.0873 (15)	0.0840 (15)	0.0092 (10)	−0.0099 (10)	−0.0187 (12)
P2	0.0319 (4)	0.0404 (5)	0.0520 (6)	0.000	0.0073 (4)	0.000
F21	0.047 (2)	0.085 (3)	0.053 (2)	0.006 (2)	0.0323 (17)	−0.007 (2)
F22	0.140 (7)	0.147 (7)	0.229 (10)	0.093 (6)	0.086 (7)	0.145 (7)
F23	0.116 (6)	0.155 (7)	0.121 (6)	0.089 (6)	0.030 (5)	0.064 (5)
F21A	0.055 (3)	0.127 (5)	0.082 (3)	0.010 (3)	−0.024 (2)	−0.016 (4)
F22A	0.108 (6)	0.212 (10)	0.256 (12)	0.066 (7)	−0.029 (7)	−0.168 (10)
F23A	0.230 (13)	0.243 (13)	0.44 (2)	−0.186 (11)	−0.146 (14)	0.251 (16)

Geometric parameters (Å, º)

Cu1—O1	1.9519 (15)	C9—C10	1.379 (4)
Cu1—N3	1.9650 (17)	C9—H9A	0.950
Cu1—N1	1.9655 (18)	C10—C11	1.380 (4)
Cu1—N2	2.0856 (17)	C10—H10A	0.950
Cu1—O3	2.3376 (16)	C11—C12	1.376 (3)
Cu1—O2	2.6235 (18)	C11—H11A	0.950
O1—C19	1.260 (3)	C12—H12A	0.950
O2—C19	1.231 (3)	C13—C18	1.392 (3)
O3—C21	1.412 (3)	C13—C14	1.395 (3)
O3—H3	0.840	C14—C15	1.384 (4)
N1—C1	1.343 (3)	C14—H14A	0.950
N1—C5	1.345 (3)	C15—C16	1.382 (4)
N2—C13	1.460 (3)	C15—H15A	0.950
N2—C6	1.484 (3)	C16—C17	1.383 (4)
N2—C7	1.488 (3)	C16—H16A	0.950
N3—C12	1.343 (3)	C17—C18	1.385 (4)
N3—C8	1.343 (3)	C17—H17A	0.950
C1—C2	1.382 (3)	C18—H18A	0.950
C1—H1A	0.950	C19—C20	1.519 (3)
C2—C3	1.378 (4)	C20—H20A	0.980
C2—H2A	0.950	C20—H20B	0.980
C3—C4	1.379 (3)	C20—H20C	0.980
C3—H3A	0.950	C21—H21A	0.980
C4—C5	1.389 (3)	C21—H21B	0.980
C4—H4A	0.950	C21—H21C	0.980
C5—C6	1.504 (3)	P1—F11	1.5947 (17)
C6—H6A	0.990	P1—F12	1.5851 (18)
C6—H6B	0.990	P1—F13	1.5883 (19)
C7—C8	1.512 (3)	P2—F23A	1.505 (5)
C7—H7A	0.990	P2—F21	1.559 (3)
C7—H7B	0.990	P2—F22	1.526 (4)
C8—C9	1.380 (3)	P2—F23	1.566 (4)
O1—Cu1—N3	97.04 (7)	C15—C14—C13	120.0 (2)
O1—Cu1—N1	98.47 (7)	C15—C14—H14A	120.0
N3—Cu1—N1	162.35 (7)	C13—C14—H14A	120.0
O1—Cu1—N2	162.21 (7)	C16—C15—C14	121.0 (3)
N3—Cu1—N2	84.03 (7)	C16—C15—H15A	119.5
N1—Cu1—N2	83.79 (7)	C14—C15—H15A	119.5
O1—Cu1—O3	106.65 (7)	C15—C16—C17	118.8 (2)
N3—Cu1—O3	82.39 (7)	C15—C16—H16A	120.6
N1—Cu1—O3	85.13 (6)	C17—C16—H16A	120.6
N2—Cu1—O3	91.11 (7)	C16—C17—C18	121.1 (3)
N3—Cu1—O2	103.72 (7)	C16—C17—H17A	119.4
N1—Cu1—O2	92.11 (7)	C18—C17—H17A	119.4
N2—Cu1—O2	107.53 (6)	C17—C18—C13	120.0 (2)
O3—Cu1—O2	160.77 (6)	C17—C18—H18A	120.0
C19—O1—Cu1	106.40 (14)	C13—C18—H18A	120.0
C19—O2—Cu1	75.53 (13)	O2—C19—O1	123.2 (2)
C21—O3—Cu1	127.04 (15)	O2—C19—C20	120.6 (2)
C21—O3—H3	106.2	O1—C19—C20	116.2 (2)
Cu1—O3—H3	123.3	C19—C20—H20A	109.5
C1—N1—C5	119.54 (19)	C19—C20—H20B	109.5
C1—N1—Cu1	125.80 (15)	H20A—C20—H20B	109.5
C5—N1—Cu1	113.69 (14)	C19—C20—H20C	109.5
C13—N2—C6	113.90 (17)	H20A—C20—H20C	109.5
C13—N2—C7	113.23 (17)	H20B—C20—H20C	109.5
C6—N2—C7	111.84 (17)	O3—C21—H21A	109.5
C13—N2—Cu1	107.32 (12)	O3—C21—H21B	109.5
C6—N2—Cu1	104.10 (12)	H21A—C21—H21B	109.5
C7—N2—Cu1	105.54 (13)	O3—C21—H21C	109.5
C12—N3—C8	119.37 (19)	H21A—C21—H21C	109.5
C12—N3—Cu1	125.31 (15)	H21B—C21—H21C	109.5
C8—N3—Cu1	114.69 (14)	F12^i—P1—F12	179.998 (1)
N1—C1—C2	121.4 (2)	F12^i—P1—F13	89.36 (13)
N1—C1—H1A	119.3	F12—P1—F13	90.64 (13)
C2—C1—H1A	119.3	F12^i—P1—F13^i	90.64 (13)
C3—C2—C1	119.2 (2)	F12—P1—F13^i	89.36 (13)
C3—C2—H2A	120.4	F13—P1—F13^i	180.0
C1—C2—H2A	120.4	F12^i—P1—F11	90.76 (10)
C2—C3—C4	119.8 (2)	F12—P1—F11	89.24 (10)
C2—C3—H3A	120.1	F13—P1—F11	89.64 (11)
C4—C3—H3A	120.1	F13^i—P1—F11	90.36 (11)
C3—C4—C5	118.5 (2)	F12^i—P1—F11^i	89.24 (10)
C3—C4—H4A	120.8	F12—P1—F11^i	90.76 (10)
C5—C4—H4A	120.8	F13—P1—F11^i	90.36 (11)
N1—C5—C4	121.6 (2)	F13^i—P1—F11^i	89.64 (11)
N1—C5—C6	116.29 (18)	F11—P1—F11^i	180.0
C4—C5—C6	121.9 (2)	F22^ii—P2—F22	90.9 (5)
N2—C6—C5	112.29 (17)	F22^ii—P2—F21	92.7 (2)
N2—C6—H6A	109.1	F22—P2—F21	89.6 (3)
C5—C6—H6A	109.1	F22^ii—P2—F21^ii	89.6 (3)
N2—C6—H6B	109.1	F22—P2—F21^ii	92.7 (2)
C5—C6—H6B	109.1	F21—P2—F21^ii	176.7 (3)
H6A—C6—H6B	107.9	F22^ii—P2—F23^ii	178.7 (4)
N2—C7—C8	112.43 (17)	F22—P2—F23^ii	90.4 (2)
N2—C7—H7A	109.1	F21—P2—F23^ii	87.1 (2)
C8—C7—H7A	109.1	F21^ii—P2—F23^ii	90.5 (2)
N2—C7—H7B	109.1	F22^ii—P2—F23	90.4 (2)
C8—C7—H7B	109.1	F22—P2—F23	178.7 (4)
H7A—C7—H7B	107.8	F21—P2—F23	90.5 (2)
N3—C8—C9	121.4 (2)	F21^ii—P2—F23	87.1 (2)
N3—C8—C7	116.36 (18)	F23^ii—P2—F23	88.3 (4)
C9—C8—C7	122.1 (2)	F23A—P2—F23A^ii	93.1 (5)
C10—C9—C8	118.9 (2)	F23A—P2—F21A^ii	92.4 (3)
C10—C9—H9A	120.6	F23A^ii—P2—F21A^ii	89.7 (3)
C8—C9—H9A	120.6	F23A—P2—F21A	89.7 (3)
C9—C10—C11	119.7 (2)	F23A^ii—P2—F21A	92.4 (3)
C9—C10—H10A	120.1	F21A^ii—P2—F21A	176.8 (5)
C11—C10—H10A	120.1	F23A—P2—F22A^ii	177.5 (4)
C12—C11—C10	118.5 (2)	F23A^ii—P2—F22A^ii	89.3 (3)
C12—C11—H11A	120.7	F21A^ii—P2—F22A^ii	86.9 (3)
C10—C11—H11A	120.7	F21A—P2—F22A^ii	90.8 (3)
N3—C12—C11	122.0 (2)	F23A—P2—F22A	89.3 (3)
N3—C12—H12A	119.0	F23A^ii—P2—F22A	177.5 (4)
C11—C12—H12A	119.0	F21A^ii—P2—F22A	90.8 (3)
C18—C13—C14	119.1 (2)	F21A—P2—F22A	86.9 (3)
C18—C13—N2	121.1 (2)	F22A^ii—P2—F22A	88.3 (5)
C14—C13—N2	119.85 (19)
N3—Cu1—O1—C19	101.72 (15)	C5—N1—C1—C2	−0.1 (3)
N1—Cu1—O1—C19	−86.74 (16)	Cu1—N1—C1—C2	−168.10 (17)
N2—Cu1—O1—C19	9.3 (3)	N1—C1—C2—C3	−0.9 (4)
O3—Cu1—O1—C19	−174.16 (14)	C1—C2—C3—C4	0.4 (4)
O2—Cu1—O1—C19	−0.14 (14)	C2—C3—C4—C5	1.0 (4)
O1—Cu1—O2—C19	0.14 (14)	C1—N1—C5—C4	1.6 (3)
N3—Cu1—O2—C19	−88.85 (16)	Cu1—N1—C5—C4	171.02 (17)
N1—Cu1—O2—C19	99.01 (16)	C1—N1—C5—C6	−173.37 (19)
N2—Cu1—O2—C19	−176.84 (15)	Cu1—N1—C5—C6	−4.0 (2)
O3—Cu1—O2—C19	17.8 (3)	C3—C4—C5—N1	−2.1 (3)
O1—Cu1—O3—C21	74.5 (2)	C3—C4—C5—C6	172.6 (2)
N3—Cu1—O3—C21	169.6 (2)	C13—N2—C6—C5	−85.1 (2)
N1—Cu1—O3—C21	−22.9 (2)	C7—N2—C6—C5	144.97 (18)
N2—Cu1—O3—C21	−106.6 (2)	Cu1—N2—C6—C5	31.5 (2)
O2—Cu1—O3—C21	59.5 (3)	N1—C5—C6—N2	−20.3 (3)
O1—Cu1—N1—C1	−11.10 (18)	C4—C5—C6—N2	164.7 (2)
N3—Cu1—N1—C1	140.1 (2)	C13—N2—C7—C8	90.1 (2)
N2—Cu1—N1—C1	−173.31 (18)	C6—N2—C7—C8	−139.57 (19)
O3—Cu1—N1—C1	95.03 (18)	Cu1—N2—C7—C8	−27.0 (2)
O2—Cu1—N1—C1	−65.90 (18)	C12—N3—C8—C9	−2.9 (3)
O1—Cu1—N1—C5	−179.73 (14)	Cu1—N3—C8—C9	−174.30 (18)
N3—Cu1—N1—C5	−28.5 (3)	C12—N3—C8—C7	173.29 (19)
N2—Cu1—N1—C5	18.07 (14)	Cu1—N3—C8—C7	1.9 (2)
O3—Cu1—N1—C5	−73.59 (15)	N2—C7—C8—N3	18.3 (3)
O2—Cu1—N1—C5	125.48 (14)	N2—C7—C8—C9	−165.6 (2)
O1—Cu1—N2—C13	−4.2 (3)	N3—C8—C9—C10	1.9 (4)
N3—Cu1—N2—C13	−98.59 (14)	C7—C8—C9—C10	−174.1 (2)
N1—Cu1—N2—C13	94.21 (14)	C8—C9—C10—C11	0.8 (4)
O3—Cu1—N2—C13	179.18 (13)	C9—C10—C11—C12	−2.4 (4)
O2—Cu1—N2—C13	3.95 (15)	C8—N3—C12—C11	1.2 (3)
O1—Cu1—N2—C6	−125.2 (2)	Cu1—N3—C12—C11	171.60 (17)
N3—Cu1—N2—C6	140.36 (14)	C10—C11—C12—N3	1.5 (4)
N1—Cu1—N2—C6	−26.85 (13)	C6—N2—C13—C18	18.6 (3)
O3—Cu1—N2—C6	58.13 (13)	C7—N2—C13—C18	147.9 (2)
O2—Cu1—N2—C6	−117.11 (13)	Cu1—N2—C13—C18	−96.0 (2)
O1—Cu1—N2—C7	116.9 (2)	C6—N2—C13—C14	−161.49 (19)
N3—Cu1—N2—C7	22.46 (13)	C7—N2—C13—C14	−32.2 (3)
N1—Cu1—N2—C7	−144.75 (14)	Cu1—N2—C13—C14	83.8 (2)
O3—Cu1—N2—C7	−59.77 (13)	C18—C13—C14—C15	0.5 (3)
O2—Cu1—N2—C7	124.99 (13)	N2—C13—C14—C15	−179.4 (2)
O1—Cu1—N3—C12	12.79 (18)	C13—C14—C15—C16	0.2 (4)
N1—Cu1—N3—C12	−138.5 (2)	C14—C15—C16—C17	−0.9 (4)
N2—Cu1—N3—C12	174.92 (18)	C15—C16—C17—C18	0.9 (4)
O3—Cu1—N3—C12	−93.15 (18)	C16—C17—C18—C13	−0.3 (4)
O2—Cu1—N3—C12	68.28 (18)	C14—C13—C18—C17	−0.4 (3)
O1—Cu1—N3—C8	−176.41 (15)	N2—C13—C18—C17	179.4 (2)
N1—Cu1—N3—C8	32.3 (3)	Cu1—O2—C19—O1	−0.2 (2)
N2—Cu1—N3—C8	−14.28 (15)	Cu1—O2—C19—C20	−179.1 (3)
O3—Cu1—N3—C8	77.65 (15)	Cu1—O1—C19—O2	0.3 (3)
O2—Cu1—N3—C8	−120.92 (15)	Cu1—O1—C19—C20	179.2 (2)

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2^iii	0.84	1.82	2.654 (2)	170

Symmetry code: (iii) −x+1/2, −y+1/2, z−1/2.