Cyclo-hexyl-methyl-ammonium N,N'-dicyclo-hexyl-N,N'-dimethyl-N''-(2,2,2-trifluoro-acet-yl)phospho-nic triamide).

In the salt, C(7)H(16)N(+)·C(16)H(28)F(3)N(3)O(2)P(-), the P atom shows tetra-hedral coordination. Two ion pairs are linked by N-H⋯O hydrogen bonds across a center of inversion. The phosphoryl and carbonyl groups are staggered [O-P-N-C = 64.8 (3)°].

Related literature

For alkali metal salts of dimethyl-N-trichlor­acetyl­amido­phosphate, see: Trush et al. (2005 ▶). For a related structure, see: Yazdanbakhsh & Sabbaghi (2007 ▶). For bond-length data, see: Corbridge (1995 ▶). For synthetic details, see: Shokol et al. (1969 ▶).

Experimental

Crystal data

C7H16N+·C16H28F3N3O2P−

M = 496.59

Monoclinic,

a = 9.183 (3) Å

b = 30.893 (7) Å

c = 9.241 (2) Å

β = 93.039 (7)°

V = 2617.9 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.15 mm−1

T = 120 (2) K

0.40 × 0.30 × 0.25 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.947, T max = 0.969

23153 measured reflections

5148 independent reflections

2673 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.113

S = 1.08

5148 reflections

304 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2001 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808040737/ng2519sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040737/ng2519Isup2.hkl

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

C7H16N+·C16H28F3N3O2P−	F(000) = 1072
Mr = 496.59	Dx = 1.260 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 365 reflections
a = 9.183 (3) Å	θ = 2–25°
b = 30.893 (7) Å	µ = 0.15 mm−1
c = 9.241 (2) Å	T = 120 K
β = 93.039 (7)°	Prism, colorless
V = 2617.9 (12) Å3	0.40 × 0.30 × 0.25 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	5148 independent reflections
Radiation source: fine-focus sealed tube	2673 reflections with I > 2σ(I)
graphite	Rint = 0.064
φ and ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.947, Tmax = 0.969	k = −38→37
23153 measured reflections	l = −11→11

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0126P)2 + 2.4P] where P = (Fo2 + 2Fc2)/3
5148 reflections	(Δ/σ)max = 0.004
304 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

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.

	x	y	z	Uiso*/Ueq
P1	0.59626 (9)	0.11209 (3)	0.00482 (9)	0.0277 (2)
F1	0.8519 (2)	0.13212 (8)	−0.3599 (2)	0.0674 (7)
F2	1.0171 (2)	0.15024 (6)	−0.2005 (2)	0.0605 (6)
F3	1.0165 (2)	0.08688 (6)	−0.2932 (2)	0.0498 (5)
O1	0.5406 (2)	0.06625 (6)	0.0163 (2)	0.0306 (5)
O2	0.9035 (2)	0.07648 (7)	−0.0331 (2)	0.0381 (6)
N1	0.7111 (3)	0.12011 (8)	−0.1208 (3)	0.0285 (6)
N2	0.4692 (3)	0.14801 (7)	−0.0417 (3)	0.0250 (6)
N3	0.6583 (3)	0.12719 (7)	0.1670 (3)	0.0280 (6)
N4	0.3080 (3)	0.01010 (8)	0.0416 (3)	0.0300 (6)
H4NA	0.3810	0.0319	0.0427	0.029 (9)*
H4NB	0.3547	−0.0172	0.0350	0.051 (11)*
C1	0.8390 (3)	0.10240 (10)	−0.1197 (3)	0.0302 (8)
C2	0.9298 (3)	0.11769 (11)	−0.2449 (4)	0.0330 (8)
C3	0.3392 (3)	0.14748 (10)	0.0448 (3)	0.0348 (8)
H3A	0.2959	0.1765	0.0455	0.052*
H3B	0.3672	0.1387	0.1444	0.052*
H3C	0.2679	0.1269	0.0023	0.052*
C4	0.4473 (3)	0.16366 (9)	−0.1935 (3)	0.0259 (7)
H4A	0.5466	0.1700	−0.2277	0.031*
C5	0.3796 (3)	0.13003 (10)	−0.2974 (3)	0.0317 (8)
H5A	0.2808	0.1225	−0.2674	0.038*
H5B	0.4395	0.1034	−0.2929	0.038*
C6	0.3694 (4)	0.14714 (11)	−0.4532 (3)	0.0411 (9)
H6A	0.4689	0.1512	−0.4873	0.049*
H6B	0.3186	0.1256	−0.5170	0.049*
C7	0.2875 (4)	0.18992 (11)	−0.4631 (4)	0.0443 (9)
H7A	0.2889	0.2012	−0.5633	0.053*
H7B	0.1845	0.1851	−0.4406	0.053*
C8	0.3553 (4)	0.22305 (10)	−0.3587 (4)	0.0411 (9)
H8A	0.2965	0.2499	−0.3638	0.049*
H8B	0.4547	0.2302	−0.3877	0.049*
C9	0.3634 (4)	0.20606 (10)	−0.2029 (3)	0.0340 (8)
H9A	0.4125	0.2277	−0.1381	0.041*
H9B	0.2636	0.2015	−0.1703	0.041*
C10	0.6862 (4)	0.09517 (10)	0.2826 (3)	0.0391 (9)
H10A	0.6866	0.1096	0.3770	0.059*
H10B	0.7811	0.0815	0.2709	0.059*
H10C	0.6095	0.0731	0.2769	0.059*
C11	0.7380 (3)	0.16853 (9)	0.1839 (3)	0.0292 (8)
H11A	0.7251	0.1840	0.0889	0.035*
C12	0.9025 (3)	0.16295 (10)	0.2143 (4)	0.0357 (8)
H12A	0.9204	0.1477	0.3079	0.043*
H12B	0.9424	0.1449	0.1374	0.043*
C13	0.9808 (4)	0.20648 (11)	0.2202 (4)	0.0472 (10)
H13A	1.0859	0.2019	0.2448	0.057*
H13B	0.9710	0.2205	0.1239	0.057*
C14	0.9170 (4)	0.23579 (11)	0.3327 (4)	0.0504 (10)
H14A	0.9658	0.2643	0.3314	0.060*
H14B	0.9357	0.2230	0.4302	0.060*
C15	0.7527 (4)	0.24187 (11)	0.3035 (4)	0.0482 (10)
H15A	0.7342	0.2574	0.2106	0.058*
H15B	0.7133	0.2597	0.3815	0.058*
C16	0.6749 (4)	0.19793 (10)	0.2965 (4)	0.0403 (9)
H16A	0.6849	0.1838	0.3927	0.048*
H16B	0.5697	0.2024	0.2722	0.048*
C17	0.2070 (3)	0.01882 (10)	−0.0858 (3)	0.0367 (9)
H17A	0.2635	0.0236	−0.1715	0.055*
H17B	0.1490	0.0447	−0.0674	0.055*
H17C	0.1420	−0.0060	−0.1026	0.055*
C18	0.2394 (3)	0.00821 (10)	0.1845 (3)	0.0299 (8)
H18A	0.1527	−0.0114	0.1745	0.036*
C19	0.3478 (4)	−0.01118 (10)	0.2964 (3)	0.0364 (9)
H19A	0.4363	0.0071	0.3050	0.044*
H19B	0.3770	−0.0404	0.2646	0.044*
C20	0.2801 (4)	−0.01433 (11)	0.4438 (3)	0.0430 (9)
H20A	0.1985	−0.0353	0.4375	0.052*
H20B	0.3541	−0.0252	0.5167	0.052*
C21	0.2246 (4)	0.02903 (11)	0.4918 (4)	0.0454 (10)
H21A	0.3080	0.0489	0.5107	0.054*
H21B	0.1745	0.0254	0.5833	0.054*
C22	0.1197 (4)	0.04878 (11)	0.3780 (3)	0.0437 (9)
H22A	0.0902	0.0779	0.4102	0.052*
H22B	0.0309	0.0306	0.3674	0.052*
C23	0.1878 (4)	0.05249 (10)	0.2320 (3)	0.0357 (8)
H23A	0.1151	0.0641	0.1590	0.043*
H23B	0.2714	0.0728	0.2397	0.043*

	U11	U22	U33	U12	U13	U23
P1	0.0272 (5)	0.0257 (5)	0.0301 (5)	−0.0010 (4)	0.0017 (4)	0.0008 (4)
F1	0.0449 (13)	0.112 (2)	0.0460 (13)	0.0198 (13)	0.0116 (11)	0.0314 (13)
F2	0.0560 (14)	0.0487 (13)	0.0793 (16)	−0.0186 (11)	0.0286 (12)	−0.0111 (12)
F3	0.0466 (13)	0.0509 (13)	0.0535 (13)	0.0069 (10)	0.0170 (10)	−0.0057 (11)
O1	0.0307 (12)	0.0241 (12)	0.0372 (13)	−0.0017 (10)	0.0042 (10)	0.0018 (10)
O2	0.0367 (14)	0.0360 (14)	0.0416 (14)	0.0078 (11)	0.0014 (11)	0.0029 (11)
N1	0.0212 (14)	0.0337 (16)	0.0304 (15)	0.0044 (12)	0.0008 (12)	0.0002 (12)
N2	0.0265 (15)	0.0242 (14)	0.0249 (14)	−0.0005 (11)	0.0056 (12)	0.0033 (11)
N3	0.0345 (16)	0.0223 (14)	0.0268 (15)	−0.0040 (12)	−0.0019 (12)	0.0018 (12)
N4	0.0331 (16)	0.0260 (16)	0.0308 (16)	0.0019 (13)	0.0009 (13)	0.0012 (12)
C1	0.031 (2)	0.0290 (19)	0.0299 (19)	−0.0028 (16)	−0.0004 (16)	−0.0024 (15)
C2	0.0264 (19)	0.032 (2)	0.040 (2)	0.0042 (16)	−0.0021 (16)	−0.0007 (16)
C3	0.036 (2)	0.0320 (19)	0.037 (2)	0.0024 (16)	0.0092 (17)	0.0039 (16)
C4	0.0234 (17)	0.0253 (17)	0.0294 (18)	0.0005 (14)	0.0044 (14)	0.0060 (14)
C5	0.0325 (19)	0.0283 (18)	0.0338 (19)	0.0005 (15)	−0.0027 (15)	0.0034 (15)
C6	0.050 (2)	0.039 (2)	0.034 (2)	−0.0105 (18)	−0.0064 (17)	−0.0030 (17)
C7	0.040 (2)	0.048 (2)	0.044 (2)	−0.0035 (18)	−0.0075 (18)	0.0165 (19)
C8	0.044 (2)	0.032 (2)	0.047 (2)	0.0049 (17)	−0.0007 (18)	0.0093 (17)
C9	0.037 (2)	0.0297 (19)	0.036 (2)	−0.0004 (15)	0.0036 (16)	0.0043 (16)
C10	0.054 (2)	0.0310 (19)	0.031 (2)	−0.0043 (17)	−0.0053 (17)	0.0073 (16)
C11	0.035 (2)	0.0261 (18)	0.0258 (18)	−0.0052 (15)	−0.0029 (15)	0.0027 (14)
C12	0.036 (2)	0.038 (2)	0.033 (2)	−0.0044 (16)	0.0010 (16)	−0.0048 (16)
C13	0.043 (2)	0.053 (2)	0.045 (2)	−0.0163 (19)	−0.0068 (19)	0.0032 (19)
C14	0.060 (3)	0.035 (2)	0.054 (3)	−0.0102 (19)	−0.015 (2)	−0.0093 (19)
C15	0.053 (3)	0.036 (2)	0.055 (3)	0.0040 (18)	−0.005 (2)	−0.0125 (19)
C16	0.040 (2)	0.033 (2)	0.047 (2)	0.0020 (17)	−0.0012 (18)	−0.0059 (17)
C17	0.041 (2)	0.041 (2)	0.0278 (19)	0.0017 (17)	−0.0061 (16)	0.0043 (16)
C18	0.032 (2)	0.0329 (19)	0.0247 (18)	−0.0010 (15)	0.0033 (15)	0.0027 (15)
C19	0.041 (2)	0.031 (2)	0.036 (2)	0.0006 (16)	−0.0051 (17)	0.0008 (16)
C20	0.058 (3)	0.038 (2)	0.032 (2)	−0.0026 (18)	−0.0092 (18)	0.0079 (17)
C21	0.062 (3)	0.047 (2)	0.027 (2)	−0.001 (2)	0.0042 (18)	−0.0015 (17)
C22	0.051 (2)	0.045 (2)	0.036 (2)	0.0031 (18)	0.0105 (18)	−0.0010 (18)
C23	0.042 (2)	0.034 (2)	0.031 (2)	0.0049 (16)	−0.0007 (16)	0.0026 (15)

P1—O1	1.511 (2)	C10—H10B	0.9800
P1—N1	1.629 (3)	C10—H10C	0.9800
P1—N3	1.643 (2)	C11—C16	1.519 (4)
P1—N2	1.651 (2)	C11—C12	1.531 (4)
F1—C2	1.326 (3)	C11—H11A	1.0000
F2—C2	1.337 (3)	C12—C13	1.525 (4)
F3—C2	1.333 (3)	C12—H12A	0.9900
O2—C1	1.258 (3)	C12—H12B	0.9900
N1—C1	1.295 (4)	C13—C14	1.520 (5)
N2—C3	1.472 (3)	C13—H13A	0.9900
N2—C4	1.487 (3)	C13—H13B	0.9900
N3—C10	1.468 (4)	C14—C15	1.530 (5)
N3—C11	1.476 (3)	C14—H14A	0.9900
N4—C17	1.484 (4)	C14—H14B	0.9900
N4—C18	1.494 (4)	C15—C16	1.534 (4)
N4—H4NA	0.9502	C15—H15A	0.9900
N4—H4NB	0.9499	C15—H15B	0.9900
C1—C2	1.536 (4)	C16—H16A	0.9900
C3—H3A	0.9800	C16—H16B	0.9900
C3—H3B	0.9800	C17—H17A	0.9800
C3—H3C	0.9800	C17—H17B	0.9800
C4—C9	1.520 (4)	C17—H17C	0.9800
C4—C5	1.525 (4)	C18—C23	1.520 (4)
C4—H4A	1.0000	C18—C19	1.520 (4)
C5—C6	1.531 (4)	C18—H18A	1.0000
C5—H5A	0.9900	C19—C20	1.530 (4)
C5—H5B	0.9900	C19—H19A	0.9900
C6—C7	1.521 (4)	C19—H19B	0.9900
C6—H6A	0.9900	C20—C21	1.509 (4)
C6—H6B	0.9900	C20—H20A	0.9900
C7—C8	1.517 (4)	C20—H20B	0.9900
C7—H7A	0.9900	C21—C22	1.516 (4)
C7—H7B	0.9900	C21—H21A	0.9900
C8—C9	1.531 (4)	C21—H21B	0.9900
C8—H8A	0.9900	C22—C23	1.521 (4)
C8—H8B	0.9900	C22—H22A	0.9900
C9—H9A	0.9900	C22—H22B	0.9900
C9—H9B	0.9900	C23—H23A	0.9900
C10—H10A	0.9800	C23—H23B	0.9900
O1—P1—N1	115.26 (13)	N3—C11—C12	113.6 (2)
O1—P1—N3	107.72 (12)	C16—C11—C12	110.5 (3)
N1—P1—N3	113.65 (13)	N3—C11—H11A	106.5
O1—P1—N2	114.29 (12)	C16—C11—H11A	106.5
N1—P1—N2	100.79 (12)	C12—C11—H11A	106.5
N3—P1—N2	104.66 (12)	C13—C12—C11	111.5 (3)
C1—N1—P1	123.4 (2)	C13—C12—H12A	109.3
C3—N2—C4	116.3 (2)	C11—C12—H12A	109.3
C3—N2—P1	115.67 (19)	C13—C12—H12B	109.3
C4—N2—P1	121.53 (19)	C11—C12—H12B	109.3
C10—N3—C11	116.1 (2)	H12A—C12—H12B	108.0
C10—N3—P1	120.7 (2)	C14—C13—C12	110.6 (3)
C11—N3—P1	119.19 (19)	C14—C13—H13A	109.5
C17—N4—C18	115.7 (2)	C12—C13—H13A	109.5
C17—N4—H4NA	106.9	C14—C13—H13B	109.5
C18—N4—H4NA	110.4	C12—C13—H13B	109.5
C17—N4—H4NB	112.1	H13A—C13—H13B	108.1
C18—N4—H4NB	103.6	C13—C14—C15	111.4 (3)
H4NA—N4—H4NB	108.1	C13—C14—H14A	109.3
O2—C1—N1	132.1 (3)	C15—C14—H14A	109.3
O2—C1—C2	114.8 (3)	C13—C14—H14B	109.3
N1—C1—C2	113.1 (3)	C15—C14—H14B	109.3
F1—C2—F3	106.1 (3)	H14A—C14—H14B	108.0
F1—C2—F2	106.4 (3)	C14—C15—C16	110.6 (3)
F3—C2—F2	106.3 (3)	C14—C15—H15A	109.5
F1—C2—C1	114.6 (3)	C16—C15—H15A	109.5
F3—C2—C1	113.0 (3)	C14—C15—H15B	109.5
F2—C2—C1	109.9 (3)	C16—C15—H15B	109.5
N2—C3—H3A	109.5	H15A—C15—H15B	108.1
N2—C3—H3B	109.5	C11—C16—C15	111.4 (3)
H3A—C3—H3B	109.5	C11—C16—H16A	109.4
N2—C3—H3C	109.5	C15—C16—H16A	109.4
H3A—C3—H3C	109.5	C11—C16—H16B	109.4
H3B—C3—H3C	109.5	C15—C16—H16B	109.4
N2—C4—C9	112.1 (2)	H16A—C16—H16B	108.0
N2—C4—C5	113.8 (2)	N4—C17—H17A	109.5
C9—C4—C5	111.3 (2)	N4—C17—H17B	109.5
N2—C4—H4A	106.4	H17A—C17—H17B	109.5
C9—C4—H4A	106.4	N4—C17—H17C	109.5
C5—C4—H4A	106.4	H17A—C17—H17C	109.5
C4—C5—C6	111.1 (2)	H17B—C17—H17C	109.5
C4—C5—H5A	109.4	N4—C18—C23	111.9 (2)
C6—C5—H5A	109.4	N4—C18—C19	108.9 (2)
C4—C5—H5B	109.4	C23—C18—C19	111.2 (3)
C6—C5—H5B	109.4	N4—C18—H18A	108.2
H5A—C5—H5B	108.0	C23—C18—H18A	108.2
C7—C6—C5	111.2 (3)	C19—C18—H18A	108.2
C7—C6—H6A	109.4	C18—C19—C20	110.4 (3)
C5—C6—H6A	109.4	C18—C19—H19A	109.6
C7—C6—H6B	109.4	C20—C19—H19A	109.6
C5—C6—H6B	109.4	C18—C19—H19B	109.6
H6A—C6—H6B	108.0	C20—C19—H19B	109.6
C8—C7—C6	111.3 (3)	H19A—C19—H19B	108.1
C8—C7—H7A	109.4	C21—C20—C19	111.4 (3)
C6—C7—H7A	109.4	C21—C20—H20A	109.3
C8—C7—H7B	109.4	C19—C20—H20A	109.3
C6—C7—H7B	109.4	C21—C20—H20B	109.3
H7A—C7—H7B	108.0	C19—C20—H20B	109.3
C7—C8—C9	111.4 (3)	H20A—C20—H20B	108.0
C7—C8—H8A	109.3	C20—C21—C22	111.5 (3)
C9—C8—H8A	109.3	C20—C21—H21A	109.3
C7—C8—H8B	109.3	C22—C21—H21A	109.3
C9—C8—H8B	109.3	C20—C21—H21B	109.3
H8A—C8—H8B	108.0	C22—C21—H21B	109.3
C4—C9—C8	110.4 (3)	H21A—C21—H21B	108.0
C4—C9—H9A	109.6	C21—C22—C23	111.7 (3)
C8—C9—H9A	109.6	C21—C22—H22A	109.3
C4—C9—H9B	109.6	C23—C22—H22A	109.3
C8—C9—H9B	109.6	C21—C22—H22B	109.3
H9A—C9—H9B	108.1	C23—C22—H22B	109.3
N3—C10—H10A	109.5	H22A—C22—H22B	107.9
N3—C10—H10B	109.5	C18—C23—C22	109.7 (3)
H10A—C10—H10B	109.5	C18—C23—H23A	109.7
N3—C10—H10C	109.5	C22—C23—H23A	109.7
H10A—C10—H10C	109.5	C18—C23—H23B	109.7
H10B—C10—H10C	109.5	C22—C23—H23B	109.7
N3—C11—C16	112.6 (3)	H23A—C23—H23B	108.2
O1—P1—N1—C1	−64.8 (3)	C4—C5—C6—C7	−54.9 (4)
N3—P1—N1—C1	60.3 (3)	C5—C6—C7—C8	55.0 (4)
N2—P1—N1—C1	171.7 (2)	C6—C7—C8—C9	−55.9 (4)
O1—P1—N2—C3	51.3 (2)	N2—C4—C9—C8	174.9 (2)
N1—P1—N2—C3	175.5 (2)	C5—C4—C9—C8	−56.4 (3)
N3—P1—N2—C3	−66.3 (2)	C7—C8—C9—C4	56.4 (4)
O1—P1—N2—C4	−99.4 (2)	C10—N3—C11—C16	−75.6 (3)
N1—P1—N2—C4	24.9 (2)	P1—N3—C11—C16	126.7 (2)
N3—P1—N2—C4	143.0 (2)	C10—N3—C11—C12	51.0 (4)
O1—P1—N3—C10	14.9 (3)	P1—N3—C11—C12	−106.8 (3)
N1—P1—N3—C10	−114.1 (2)	N3—C11—C12—C13	176.0 (3)
N2—P1—N3—C10	136.9 (2)	C16—C11—C12—C13	−56.3 (4)
O1—P1—N3—C11	171.6 (2)	C11—C12—C13—C14	56.4 (4)
N1—P1—N3—C11	42.6 (3)	C12—C13—C14—C15	−56.2 (4)
N2—P1—N3—C11	−66.4 (2)	C13—C14—C15—C16	55.9 (4)
P1—N1—C1—O2	1.1 (5)	N3—C11—C16—C15	−175.8 (3)
P1—N1—C1—C2	−176.0 (2)	C12—C11—C16—C15	56.0 (4)
O2—C1—C2—F1	157.9 (3)	C14—C15—C16—C11	−55.9 (4)
N1—C1—C2—F1	−24.4 (4)	C17—N4—C18—C23	−69.9 (3)
O2—C1—C2—F3	36.2 (4)	C17—N4—C18—C19	166.7 (3)
N1—C1—C2—F3	−146.1 (3)	N4—C18—C19—C20	−179.0 (3)
O2—C1—C2—F2	−82.3 (3)	C23—C18—C19—C20	57.2 (3)
N1—C1—C2—F2	95.3 (3)	C18—C19—C20—C21	−55.3 (4)
C3—N2—C4—C9	48.6 (3)	C19—C20—C21—C22	54.5 (4)
P1—N2—C4—C9	−161.0 (2)	C20—C21—C22—C23	−55.5 (4)
C3—N2—C4—C5	−78.8 (3)	N4—C18—C23—C22	−179.7 (3)
P1—N2—C4—C5	71.7 (3)	C19—C18—C23—C22	−57.7 (4)
N2—C4—C5—C6	−176.2 (2)	C21—C22—C23—C18	56.5 (4)
C9—C4—C5—C6	56.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4NA···O1	0.95	1.84	2.771 (3)	167
N4—H4NB···O1i	0.95	1.87	2.804 (3)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4NA⋯O1	0.95	1.84	2.771 (3)	167
N4—H4NB⋯O1i	0.95	1.87	2.804 (3)	168

Symmetry code: (i) .