Bis(pyrrolidin-1-yl)phosphinic (2,4-di-fluoro-benzo-yl)amide.

The P atom in the title mol-ecule, C(15)H(20)F(2)N(3)O(2)P, is in a distorted tetra-hedral P(O)(N)(N)(2) environment. The phosphoryl group and the NH unit adopt a syn orientation with respect to each other. An F atom at position 2 and an H atom at position 6 are found to occupy similar sites in a 0.70:0.30 ratio and were refined with fixed occupancies. The pyrrolidin-1-yl rings are disordered over two sets of sites, with site occupancies of 0.566 (6) and 0.434 (6), and were refined using a two-part model. In the crystal, hydrogen-bonded dimers linked by pairs of N-H⋯O(P) hydrogen bonds generate an R(2) (2)(8) ring motif.

Related literature

For background and related crystal structures, see: Pourayoubi et al. (2011 ▶, 2012 ▶). For the preparation of the starting compound, see: Pourayoubi et al. (2012 ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H20F2N3O2P

M = 343.31

Monoclinic,

a = 9.1028 (3) Å

b = 9.9477 (2) Å

c = 18.5465 (5) Å

β = 92.268 (3)°

V = 1678.11 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 173 K

0.40 × 0.30 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.926, T max = 0.962

17134 measured reflections

4339 independent reflections

3828 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.108

S = 1.03

4339 reflections

300 parameters

25 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812034733/pv2575sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034733/pv2575Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812034733/pv2575Isup3.cml

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

C15H20F2N3O2P	F(000) = 720
Mr = 343.31	Dx = 1.359 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7108 reflections
a = 9.1028 (3) Å	θ = 3.3–32.3°
b = 9.9477 (2) Å	µ = 0.20 mm−1
c = 18.5465 (5) Å	T = 173 K
β = 92.268 (3)°	Block, colorless
V = 1678.11 (8) Å3	0.40 × 0.30 × 0.20 mm
Z = 4

Oxford Diffraction Xcalibur Eos Gemini diffractometer	4339 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3828 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
Detector resolution: 16.1500 pixels mm-1	θmax = 28.7°, θmin = 3.3°
ω scans	h = −12→7
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −12→13
Tmin = 0.926, Tmax = 0.962	l = −24→25
17134 measured reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0515P)2 + 0.7979P] where P = (Fo2 + 2Fc2)/3
4339 reflections	(Δ/σ)max = 0.001
300 parameters	Δρmax = 0.38 e Å−3
25 restraints	Δρmin = −0.30 e Å−3

Experimental. IR (KBr, ν, cm-1): 3067, 2973, 2892, 1685, 1623, 1457, 1258, 1220, 1177, 1129, 1087, 1011, 968, 859, 811. 1H NMR (400.22 MHz, DMSO-d6, 293.9 K, TMS): 1.57 (m, 8H), 3.14 (m, 8H), 7.19 (t, 1H, Ar—H), 7.36 (t, 3J[(H,H),(H,F)] = 10.0 Hz, 1H, Ar—H), 7.66 (m, 1H, Ar—H), 9.26 p.p.m. (s, 1H, N—H). 13C NMR (100.64 MHz, DMSO-d6, 293.9 K, TMS): 26.38 (d, 3J(C,P) = 9.1 Hz, 4C), 46.34 (d, 2J(C,P) = 5.0 Hz, 4C), 105.03 (t, 2J(C,F) = 26.2 Hz, 1C, Ar—C), 112.16 (dd, 2J(C,F) = 21.6 Hz, 4J(C,F) = 3.5 Hz, 1C, Ar—C), 121.61 (m, 1C, Ar—C), 132.22 (dd, 3J(C,F) = 4.0 Hz and 11.1 Hz, 1C, Ar—C), 160.29 (d, 3J(C,F) = 13.6, 1J(C,F) = 252.1 Hz, 1C, Ar—C), 164.06 (d, 3J(C,F) = 12.1, 1J(C,F) = 251.1 Hz, 1C, Ar—C), 165.37 p.p.m. (s, 1C, C(O)). 31P{1H} NMR (162.01 MHz, DMSO-d6, 293.9 K, 85% H3PO4): 5.66 p.p.m. (s).

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	Occ. (<1)
P1	0.59836 (4)	0.47159 (3)	0.114620 (16)	0.02308 (10)
F1	0.59877 (19)	1.01499 (17)	0.13543 (9)	0.0434 (4)	0.70
F1A	0.2448 (4)	0.6940 (3)	0.0502 (2)	0.0405 (8)	0.30
F2	0.17516 (14)	1.14989 (11)	0.00596 (7)	0.0617 (3)
O1	0.53714 (12)	0.37387 (9)	0.06124 (5)	0.0316 (2)
O3	0.57983 (14)	0.75048 (11)	0.18642 (6)	0.0425 (3)
N1	0.53996 (13)	0.62346 (11)	0.08554 (6)	0.0264 (2)
H1N	0.5064 (18)	0.6275 (17)	0.0427 (7)	0.032*
N2	0.54212 (13)	0.44054 (13)	0.19479 (6)	0.0317 (3)
N3	0.77636 (14)	0.47924 (12)	0.12213 (7)	0.0326 (3)
C1	0.47337 (16)	0.98082 (14)	0.09944 (7)	0.0289 (3)
H1A	0.571 (4)	1.003 (9)	0.117 (4)	0.035*	0.30
C2	0.38927 (18)	1.08460 (14)	0.07115 (8)	0.0351 (3)
H2A	0.4184	1.1758	0.0770	0.042*
C3	0.26117 (18)	1.05011 (15)	0.03401 (9)	0.0365 (3)
C4	0.21545 (16)	0.91998 (16)	0.02352 (8)	0.0354 (3)
H4A	0.1260	0.9000	−0.0024	0.042*
C5	0.30424 (15)	0.81899 (14)	0.05208 (7)	0.0285 (3)
H1	0.278 (4)	0.7283 (15)	0.0411 (18)	0.034*	0.70
C6	0.43458 (14)	0.84645 (12)	0.09091 (6)	0.0239 (2)
C7	0.52591 (15)	0.73730 (13)	0.12577 (7)	0.0264 (3)
C8	0.6225 (6)	0.4742 (8)	0.2636 (3)	0.0272 (17)	0.566 (6)
H8A	0.6806	0.5577	0.2591	0.033*	0.566 (6)
H8B	0.6888	0.4002	0.2796	0.033*	0.566 (6)
C9	0.4996 (10)	0.4928 (11)	0.3144 (4)	0.065 (2)	0.566 (6)
H9A	0.4666	0.5877	0.3146	0.078*	0.566 (6)
H9B	0.5314	0.4667	0.3641	0.078*	0.566 (6)
C10	0.3769 (6)	0.4013 (8)	0.2855 (2)	0.0748 (16)	0.566 (6)
H10A	0.2804	0.4304	0.3028	0.090*	0.566 (6)
H10B	0.3948	0.3069	0.3003	0.090*	0.566 (6)
C11	0.3829 (8)	0.4168 (11)	0.2035 (4)	0.0489 (19)	0.566 (6)
H11A	0.3491	0.3341	0.1781	0.059*	0.566 (6)
H11B	0.3231	0.4940	0.1858	0.059*	0.566 (6)
C8A	0.6167 (14)	0.4736 (16)	0.2641 (6)	0.063 (5)	0.434 (6)
H8AA	0.6565	0.5662	0.2632	0.076*	0.434 (6)
H8AB	0.6987	0.4103	0.2747	0.076*	0.434 (6)
C9A	0.5017 (15)	0.4612 (18)	0.3196 (8)	0.085 (5)	0.434 (6)
H9AA	0.5180	0.5274	0.3589	0.102*	0.434 (6)
H9AB	0.5003	0.3696	0.3404	0.102*	0.434 (6)
C10A	0.3614 (6)	0.4907 (8)	0.2760 (3)	0.0644 (17)	0.434 (6)
H10C	0.3506	0.5875	0.2646	0.077*	0.434 (6)
H10D	0.2731	0.4583	0.3003	0.077*	0.434 (6)
C11A	0.3941 (13)	0.4072 (19)	0.2095 (7)	0.079 (5)	0.434 (6)
H11C	0.3842	0.3099	0.2196	0.095*	0.434 (6)
H11D	0.3267	0.4313	0.1683	0.095*	0.434 (6)
C12	0.8722 (3)	0.5949 (3)	0.1329 (3)	0.0476 (10)	0.566 (6)
H12A	0.8306	0.6592	0.1673	0.057*	0.566 (6)
H12B	0.8873	0.6417	0.0866	0.057*	0.566 (6)
C13	1.0112 (5)	0.5376 (5)	0.1622 (6)	0.118 (3)	0.566 (6)
H13A	1.0949	0.5834	0.1402	0.142*	0.566 (6)
H13B	1.0191	0.5532	0.2150	0.142*	0.566 (6)
C14	1.0185 (4)	0.3994 (5)	0.1484 (3)	0.0579 (11)	0.566 (6)
H14A	1.0650	0.3506	0.1898	0.069*	0.566 (6)
H14B	1.0740	0.3810	0.1047	0.069*	0.566 (6)
C15	0.8656 (9)	0.3626 (9)	0.1378 (6)	0.065 (3)	0.566 (6)
H15A	0.8549	0.2979	0.0973	0.078*	0.566 (6)
H15B	0.8314	0.3181	0.1818	0.078*	0.566 (6)
C12A	0.8614 (5)	0.5743 (6)	0.0805 (4)	0.0635 (17)	0.434 (6)
H12C	0.8512	0.6670	0.0991	0.076*	0.434 (6)
H12D	0.8299	0.5725	0.0288	0.076*	0.434 (6)
C13A	1.0174 (6)	0.5242 (7)	0.0916 (6)	0.081 (2)	0.434 (6)
H13C	1.0757	0.5418	0.0487	0.098*	0.434 (6)
H13D	1.0668	0.5667	0.1343	0.098*	0.434 (6)
C14A	0.9971 (6)	0.3782 (7)	0.1029 (6)	0.082 (2)	0.434 (6)
H14C	1.0803	0.3433	0.1335	0.099*	0.434 (6)
H14D	0.9982	0.3316	0.0558	0.099*	0.434 (6)
C15A	0.8561 (9)	0.3470 (9)	0.1381 (4)	0.0336 (18)	0.434 (6)
H15C	0.8710	0.3310	0.1906	0.040*	0.434 (6)
H15D	0.8046	0.2694	0.1153	0.040*	0.434 (6)

	U11	U22	U33	U12	U13	U23
P1	0.02981 (18)	0.02096 (16)	0.01801 (16)	0.00199 (12)	−0.00475 (11)	0.00008 (11)
F1	0.0477 (8)	0.0307 (7)	0.0504 (10)	−0.0092 (6)	−0.0175 (6)	−0.0046 (6)
F1A	0.0350 (18)	0.0305 (16)	0.055 (2)	−0.0053 (12)	−0.0065 (14)	−0.0031 (14)
F2	0.0686 (7)	0.0373 (6)	0.0781 (8)	0.0235 (5)	−0.0103 (6)	0.0113 (5)
O1	0.0503 (6)	0.0211 (4)	0.0227 (4)	0.0007 (4)	−0.0091 (4)	−0.0013 (3)
O3	0.0668 (8)	0.0314 (5)	0.0276 (5)	0.0033 (5)	−0.0184 (5)	−0.0070 (4)
N1	0.0376 (6)	0.0214 (5)	0.0193 (5)	0.0052 (4)	−0.0090 (4)	−0.0025 (4)
N2	0.0337 (6)	0.0406 (7)	0.0205 (5)	−0.0028 (5)	−0.0027 (4)	0.0009 (5)
N3	0.0317 (6)	0.0307 (6)	0.0349 (6)	0.0038 (5)	−0.0034 (5)	0.0060 (5)
C1	0.0343 (7)	0.0247 (6)	0.0277 (6)	−0.0036 (5)	0.0024 (5)	−0.0037 (5)
C2	0.0492 (9)	0.0203 (6)	0.0365 (7)	−0.0001 (6)	0.0090 (6)	0.0004 (5)
C3	0.0420 (8)	0.0285 (7)	0.0393 (8)	0.0126 (6)	0.0042 (6)	0.0053 (6)
C4	0.0319 (7)	0.0350 (7)	0.0388 (8)	0.0057 (6)	−0.0031 (6)	0.0000 (6)
C5	0.0308 (7)	0.0235 (6)	0.0310 (6)	0.0001 (5)	−0.0001 (5)	−0.0020 (5)
C6	0.0300 (6)	0.0206 (6)	0.0213 (5)	0.0015 (5)	0.0021 (5)	−0.0020 (4)
C7	0.0334 (7)	0.0222 (6)	0.0232 (6)	0.0002 (5)	−0.0038 (5)	−0.0023 (5)
C8	0.031 (2)	0.040 (5)	0.011 (3)	0.004 (2)	−0.002 (2)	0.001 (3)
C9	0.073 (5)	0.094 (4)	0.029 (3)	−0.020 (3)	0.015 (3)	−0.026 (3)
C10	0.073 (3)	0.108 (5)	0.045 (2)	−0.016 (3)	0.023 (2)	0.007 (3)
C11	0.027 (2)	0.085 (5)	0.035 (3)	−0.010 (2)	0.014 (2)	0.001 (3)
C8A	0.096 (8)	0.054 (9)	0.038 (7)	−0.004 (6)	−0.025 (6)	0.005 (6)
C9A	0.073 (7)	0.150 (12)	0.033 (4)	0.011 (6)	0.008 (4)	0.025 (6)
C10A	0.057 (3)	0.091 (5)	0.047 (3)	0.014 (3)	0.020 (2)	0.007 (3)
C11A	0.065 (6)	0.134 (12)	0.037 (4)	−0.022 (6)	−0.017 (4)	−0.003 (5)
C12	0.0330 (15)	0.0340 (15)	0.076 (3)	−0.0070 (11)	−0.0001 (15)	0.0075 (16)
C13	0.038 (2)	0.063 (3)	0.249 (10)	−0.003 (2)	−0.038 (4)	−0.015 (4)
C14	0.0310 (16)	0.061 (2)	0.080 (3)	0.0046 (15)	−0.0115 (18)	0.014 (2)
C15	0.048 (4)	0.052 (4)	0.095 (5)	0.010 (3)	0.002 (3)	0.036 (3)
C12A	0.043 (2)	0.053 (3)	0.095 (5)	−0.009 (2)	0.004 (3)	0.019 (3)
C13A	0.031 (2)	0.074 (4)	0.139 (7)	−0.005 (2)	0.009 (3)	0.024 (4)
C14A	0.030 (2)	0.069 (4)	0.148 (8)	0.013 (2)	0.000 (4)	−0.003 (5)
C15A	0.029 (3)	0.033 (3)	0.037 (3)	0.015 (2)	−0.014 (2)	−0.009 (3)

P1—O1	1.4805 (10)	C10—H10A	0.9900
P1—N2	1.6213 (12)	C10—H10B	0.9900
P1—N3	1.6226 (13)	C11—H11A	0.9900
P1—N1	1.6832 (11)	C11—H11B	0.9900
F1—C1	1.3431 (19)	C8A—C9A	1.502 (14)
F1—H1A	0.43 (5)	C8A—H8AA	0.9900
F1A—C5	1.356 (3)	C8A—H8AB	0.9900
F1A—H1	0.49 (2)	C9A—C10A	1.513 (14)
F2—C3	1.3552 (17)	C9A—H9AA	0.9900
O3—C7	1.2165 (16)	C9A—H9AB	0.9900
N1—C7	1.3649 (16)	C10A—C11A	1.526 (13)
N1—H1N	0.841 (13)	C10A—H10C	0.9900
N2—C11A	1.425 (11)	C10A—H10D	0.9900
N2—C8A	1.467 (11)	C11A—H11C	0.9900
N2—C11	1.484 (6)	C11A—H11D	0.9900
N2—C8	1.484 (6)	C12—C13	1.472 (5)
N3—C15	1.440 (9)	C12—H12A	0.9900
N3—C12	1.453 (3)	C12—H12B	0.9900
N3—C12A	1.462 (5)	C13—C14	1.400 (7)
N3—C15A	1.526 (8)	C13—H13A	0.9900
C1—C2	1.377 (2)	C13—H13B	0.9900
C1—C6	1.3900 (18)	C14—C15	1.445 (9)
C1—H1A	0.957 (10)	C14—H14A	0.9900
C2—C3	1.374 (2)	C14—H14B	0.9900
C2—H2A	0.9500	C15—H15A	0.9900
C3—C4	1.371 (2)	C15—H15B	0.9900
C4—C5	1.3817 (19)	C12A—C13A	1.512 (7)
C4—H4A	0.9500	C12A—H12C	0.9900
C5—C6	1.3905 (18)	C12A—H12D	0.9900
C5—H1	0.953 (10)	C13A—C14A	1.480 (8)
C6—C7	1.4985 (17)	C13A—H13C	0.9900
C8—C9	1.503 (8)	C13A—H13D	0.9900
C8—H8A	0.9900	C14A—C15A	1.495 (10)
C8—H8B	0.9900	C14A—H14C	0.9900
C9—C10	1.521 (9)	C14A—H14D	0.9900
C9—H9A	0.9900	C15A—H15C	0.9900
C9—H9B	0.9900	C15A—H15D	0.9900
C10—C11	1.532 (9)
O1—P1—N2	111.35 (6)	H11A—C11—H11B	109.3
O1—P1—N3	115.87 (7)	N2—C8A—C9A	105.7 (10)
N2—P1—N3	106.30 (6)	N2—C8A—H8AA	110.6
O1—P1—N1	105.63 (5)	C9A—C8A—H8AA	110.6
N2—P1—N1	110.96 (6)	N2—C8A—H8AB	110.6
N3—P1—N1	106.68 (6)	C9A—C8A—H8AB	110.6
C7—N1—P1	127.22 (9)	H8AA—C8A—H8AB	108.7
C7—N1—H1N	116.0 (12)	C8A—C9A—C10A	102.4 (10)
P1—N1—H1N	116.3 (12)	C8A—C9A—H9AA	111.3
C11A—N2—C8A	107.0 (7)	C10A—C9A—H9AA	111.3
C8A—N2—C11	111.2 (6)	C8A—C9A—H9AB	111.3
C11A—N2—C8	109.0 (6)	C10A—C9A—H9AB	111.3
C11—N2—C8	113.1 (4)	H9AA—C9A—H9AB	109.2
C11A—N2—P1	123.8 (6)	C9A—C10A—C11A	98.0 (9)
C8A—N2—P1	127.5 (5)	C9A—C10A—H10C	112.2
C11—N2—P1	118.4 (3)	C11A—C10A—H10C	112.2
C8—N2—P1	125.6 (2)	C9A—C10A—H10D	112.2
C15—N3—C12	106.2 (4)	C11A—C10A—H10D	112.2
C15—N3—C12A	108.8 (4)	H10C—C10A—H10D	109.8
C12—N3—C15A	112.2 (3)	N2—C11A—C10A	104.1 (9)
C12A—N3—C15A	113.7 (4)	N2—C11A—H11C	110.9
C15—N3—P1	122.2 (4)	C10A—C11A—H11C	110.9
C12—N3—P1	129.90 (15)	N2—C11A—H11D	110.9
C12A—N3—P1	122.2 (2)	C10A—C11A—H11D	110.9
C15A—N3—P1	116.2 (3)	H11C—C11A—H11D	108.9
F1—C1—C2	116.64 (14)	N3—C12—C13	104.3 (3)
F1—C1—C6	120.47 (14)	N3—C12—H12A	110.9
C2—C1—C6	122.88 (13)	C13—C12—H12A	110.9
C2—C1—H1A	117 (5)	N3—C12—H12B	110.9
C6—C1—H1A	119 (5)	C13—C12—H12B	110.9
C3—C2—C1	116.86 (13)	H12A—C12—H12B	108.9
C3—C2—H2A	121.6	C14—C13—C12	111.0 (4)
C1—C2—H2A	121.6	C14—C13—H13A	109.4
F2—C3—C4	118.00 (15)	C12—C13—H13A	109.4
F2—C3—C2	118.39 (14)	C14—C13—H13B	109.4
C4—C3—C2	123.62 (13)	C12—C13—H13B	109.4
C3—C4—C5	117.54 (14)	H13A—C13—H13B	108.0
C3—C4—H4A	121.2	C13—C14—C15	102.8 (5)
C5—C4—H4A	121.2	C13—C14—H14A	111.2
F1A—C5—C4	115.48 (19)	C15—C14—H14A	111.2
F1A—C5—C6	121.66 (19)	C13—C14—H14B	111.2
C4—C5—C6	122.00 (13)	C15—C14—H14B	111.2
C4—C5—H1	118 (2)	H14A—C14—H14B	109.1
C6—C5—H1	120 (2)	N3—C15—C14	110.8 (6)
C1—C6—C5	117.10 (12)	N3—C15—H15A	109.5
C1—C6—C7	120.90 (12)	C14—C15—H15A	109.5
C5—C6—C7	121.91 (11)	N3—C15—H15B	109.5
O3—C7—N1	123.49 (12)	C14—C15—H15B	109.5
O3—C7—C6	121.16 (12)	H15A—C15—H15B	108.1
N1—C7—C6	115.32 (11)	N3—C12A—C13A	103.2 (4)
N2—C8—C9	102.3 (5)	N3—C12A—H12C	111.1
N2—C8—H8A	111.3	C13A—C12A—H12C	111.1
C9—C8—H8A	111.3	N3—C12A—H12D	111.1
N2—C8—H8B	111.3	C13A—C12A—H12D	111.1
C9—C8—H8B	111.3	H12C—C12A—H12D	109.1
H8A—C8—H8B	109.2	C14A—C13A—C12A	102.8 (4)
C8—C9—C10	105.1 (6)	C14A—C13A—H13C	111.2
C8—C9—H9A	110.7	C12A—C13A—H13C	111.2
C10—C9—H9A	110.7	C14A—C13A—H13D	111.2
C8—C9—H9B	110.7	C12A—C13A—H13D	111.2
C10—C9—H9B	110.7	H13C—C13A—H13D	109.1
H9A—C9—H9B	108.8	C13A—C14A—C15A	112.3 (5)
C9—C10—C11	103.6 (5)	C13A—C14A—H14C	109.1
C9—C10—H10A	111.0	C15A—C14A—H14C	109.1
C11—C10—H10A	111.0	C13A—C14A—H14D	109.1
C9—C10—H10B	111.0	C15A—C14A—H14D	109.1
C11—C10—H10B	111.0	H14C—C14A—H14D	107.9
H10A—C10—H10B	109.0	C14A—C15A—N3	98.4 (6)
N2—C11—C10	101.4 (6)	C14A—C15A—H15C	112.1
N2—C11—H11A	111.5	N3—C15A—H15C	112.1
C10—C11—H11A	111.5	C14A—C15A—H15D	112.1
N2—C11—H11B	111.5	N3—C15A—H15D	112.1
C10—C11—H11B	111.5	H15C—C15A—H15D	109.7
O1—P1—N1—C7	157.09 (12)	C5—C6—C7—O3	−137.01 (15)
N2—P1—N1—C7	36.30 (14)	C1—C6—C7—N1	−142.04 (13)
N3—P1—N1—C7	−79.07 (13)	C5—C6—C7—N1	41.38 (18)
O1—P1—N2—C11A	−43.6 (9)	C11A—N2—C8—C9	−14.5 (11)
N3—P1—N2—C11A	−170.6 (9)	C8A—N2—C8—C9	−8 (27)
N1—P1—N2—C11A	73.7 (9)	C11—N2—C8—C9	−9.0 (9)
O1—P1—N2—C8A	153.3 (8)	P1—N2—C8—C9	151.5 (5)
N3—P1—N2—C8A	26.3 (8)	N2—C8—C9—C10	29.3 (9)
N1—P1—N2—C8A	−89.3 (8)	C8—C9—C10—C11	−39.2 (10)
O1—P1—N2—C11	−48.0 (5)	C11A—N2—C11—C10	37 (7)
N3—P1—N2—C11	−175.0 (5)	C8A—N2—C11—C10	−14.5 (10)
N1—P1—N2—C11	69.4 (5)	C8—N2—C11—C10	−14.4 (8)
O1—P1—N2—C8	152.4 (4)	P1—N2—C11—C10	−176.5 (4)
N3—P1—N2—C8	25.4 (4)	C9—C10—C11—N2	31.8 (9)
N1—P1—N2—C8	−90.2 (4)	C11A—N2—C8A—C9A	−1.6 (15)
O1—P1—N3—C15	−55.4 (5)	C11—N2—C8A—C9A	3.8 (13)
N2—P1—N3—C15	68.9 (5)	C8—N2—C8A—C9A	−175 (28)
N1—P1—N3—C15	−172.6 (5)	P1—N2—C8A—C9A	163.7 (8)
O1—P1—N3—C12	141.4 (3)	N2—C8A—C9A—C10A	−27.4 (14)
N2—P1—N3—C12	−94.3 (3)	C8A—C9A—C10A—C11A	43.4 (14)
N1—P1—N3—C12	24.2 (3)	C8A—N2—C11A—C10A	30.0 (14)
O1—P1—N3—C12A	92.4 (4)	C11—N2—C11A—C10A	−100 (8)
N2—P1—N3—C12A	−143.3 (4)	C8—N2—C11A—C10A	30.2 (13)
N1—P1—N3—C12A	−24.8 (4)	P1—N2—C11A—C10A	−136.0 (7)
O1—P1—N3—C15A	−54.8 (3)	C9A—C10A—C11A—N2	−45.7 (14)
N2—P1—N3—C15A	69.5 (3)	C15—N3—C12—C13	−5.9 (7)
N1—P1—N3—C15A	−172.0 (3)	C12A—N3—C12—C13	−105.9 (6)
F1—C1—C2—C3	179.74 (15)	C15A—N3—C12—C13	−5.0 (6)
C6—C1—C2—C3	0.9 (2)	P1—N3—C12—C13	159.3 (5)
C1—C2—C3—F2	179.47 (13)	N3—C12—C13—C14	18.5 (8)
C1—C2—C3—C4	−0.7 (2)	C12—C13—C14—C15	−22.6 (9)
F2—C3—C4—C5	179.73 (14)	C12—N3—C15—C14	−7.8 (8)
C2—C3—C4—C5	−0.1 (2)	C12A—N3—C15—C14	34.0 (8)
C3—C4—C5—F1A	170.3 (2)	P1—N3—C15—C14	−174.4 (4)
C3—C4—C5—C6	0.8 (2)	C13—C14—C15—N3	18.6 (9)
F1—C1—C6—C5	−179.07 (14)	C15—N3—C12A—C13A	−15.8 (7)
C2—C1—C6—C5	−0.2 (2)	C12—N3—C12A—C13A	77.2 (6)
F1—C1—C6—C7	4.2 (2)	C15A—N3—C12A—C13A	−19.4 (7)
C2—C1—C6—C7	−176.98 (13)	P1—N3—C12A—C13A	−167.4 (4)
F1A—C5—C6—C1	−169.5 (2)	N3—C12A—C13A—C14A	28.8 (8)
C4—C5—C6—C1	−0.6 (2)	C12A—C13A—C14A—C15A	−30.9 (10)
F1A—C5—C6—C7	7.2 (3)	C13A—C14A—C15A—N3	18.5 (8)
C4—C5—C6—C7	176.09 (13)	C15—N3—C15A—C14A	−33 (6)
P1—N1—C7—O3	14.1 (2)	C12—N3—C15A—C14A	−42.0 (5)
P1—N1—C7—C6	−164.21 (10)	C12A—N3—C15A—C14A	1.4 (6)
C1—C6—C7—O3	39.6 (2)	P1—N3—C15A—C14A	151.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.84 (1)	1.95 (1)	2.7845 (14)	170 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.84 (1)	1.95 (1)	2.7845 (14)	170 (2)

Symmetry code: (i) .