Hirshfeld surface analysis of new phosphoramidates

Tarahhomi, A.; Pourayoubi, M.; Golen, J.A.; Zargaran, P.; Elahi, B.; Rheingold, A.L.; Leyva Ramírez, M.A.; Mancilla Percino, T.

doi:10.1107/S2052519213009445

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Hirshfeld surface analysis of new phosphoramidates

A. Tarahhomi, M. Pourayoubi, J. A. Golen, P. Zargaran, B. Elahi, A. L. Rheingold, M. A. Leyva Ramírez and T. Mancilla Percino

Hirshfeld surfaces and two-dimensional fingerprint plots are used to visualize and analyze intermolecular interactions in six new phosphoramidate structures, [2,6-F₂—C₆H₃C(O)NH]P(O)[X]₂ {X = N(C₂H₅)₂ (1), [X]₂ = NHCH₂C(CH₃)₂CH₂NH and with one CH₃OH solvated molecule (2)}, [C₆H₅O]₂P(O)Y [Y = NC₄H₈O (3), NHC₆H₄(3-Br) (4)] and [Z]₂P(O)OP(O)[Z]₂ [Z = N(CH₃)(CH₂C₆H₅) (5), NHC₆H₄(4-CH₃) (6)]. Study of the short intermolecular contacts in structures (1)–(6) by Hirshfeld surfaces demonstrate that the O atom of P=O is a better H-atom acceptor than the O atom of C=O for (1) and (2), and also relative to the O atom of the C₆H₅O group for (3) and (4), and relative to the bridge O atom of the P(O)OP(O) segment for (5) and (6). The results confirm that the crystal packing is related to the kind of substituent linked to the P atom. Compounds (1), (2), (4) and (6), with characteristic N—H

O hydrogen bonds, show a pair of intense spikes (including the intermolecular H

O contacts) in the fingerprint plots, summarizing the major features of each structure in the related two-dimensional plot. For (3) and (5), without any N—H unit, the two short spikes are observed for (3) but are absent for (5). The upper d_e and d_i values (distances to the Hirshfeld surfaces for the nearest atoms outside and inside) in the fingerprint plots are more compact in (3) than in (4), and in (5) than in (6), reflecting the more efficient packing in (3) and (5). The tertiary N atoms of (3) and (5) do not take part in any intermolecular contacts involving H atoms. Moreover, structures (3)–(6) show greater contribution from C

H contacts relative to O

H contacts. Finally, Hirshfeld surfaces and fingerprint plots are employed for a comparison of the two independent molecules in the asymmetric unit of (1) and also, for a comparison of (6), in the orthorhombic crystal system, with the previously reported monoclinic polymorph (Pourayoubi, Fadaei et al., 2012).

Keywords: Hirshfeld surface analysis; two-dimensional fingerprint plots; hydrogen bonding.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2052519213009445/so5063sup1.cif Contains datablocks I, II, III, IV, V, VI, New_Global_Publ_Block
	Structure factor file (CIF format) https://doi.org/10.1107/S2052519213009445/so5063Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2052519213009445/so5063IIsup3.hkl Contains datablock atar17
	Structure factor file (CIF format) https://doi.org/10.1107/S2052519213009445/so5063IIIsup4.hkl Contains datablock tm16
	Structure factor file (CIF format) https://doi.org/10.1107/S2052519213009445/so5063IVsup5.hkl Contains datablock tm18
	Structure factor file (CIF format) https://doi.org/10.1107/S2052519213009445/so5063Vsup6.hkl Contains datablock V
	Structure factor file (CIF format) https://doi.org/10.1107/S2052519213009445/so5063VIsup7.hkl Contains datablock atar29
	Portable Document Format (PDF) file https://doi.org/10.1107/S2052519213009445/so5063sup8.pdf Table of bond lengths, angles and torsion angles

CCDC references: 821702; 821706; 924019; 924020; 924021; 924022

Computing details top

Data collection: APEX2 (Bruker, 2005) for (I), (II), (V), (VI); Collect (Nonius, 2001) for (III), (IV). Cell refinement: SAINT (Bruker, 2005) for (I), (II), (V), (VI); SCALEPACK (Otwinowski & Minor, 1997) for (III), (IV). Data reduction: SAINT (Bruker, 2005) for (I), (II), (V), (VI); DENZO and SCALEPACK (Otwinowski & Minor, 1997) for (III), (IV). For all compounds, program(s) used to solve structure: SHELXS-97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL-97 (Sheldrick, 2008). Molecular graphics: Mercury (Macrae et al., 2008); SHELXTL (Sheldrick, 2008) for (I), (II), (VI); SHELXTL (Sheldrick, 2008) for (III), (IV), (V). Software used to prepare material for publication: SHELXTL (Sheldrick, 2008); enCIFer (Allen et al., 2004) for (I), (II), (V), (VI); WinGX (Farrugia, 1999); enCIFer (Allen et al., 2004) for (III), (IV).

(I) top

Crystal data top

C₁₅H₂₄F₂N₃O₂P	Z = 4
M_r = 347.34	F(000) = 736
Triclinic, P1	D_x = 1.322 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8932 (17) Å	Cell parameters from 9914 reflections
b = 10.5022 (19) Å	θ = 2.6–27.9°
c = 19.228 (4) Å	µ = 0.19 mm⁻¹
α = 79.853 (3)°	T = 100 K
β = 81.589 (2)°	BLOCK, colourless
γ = 62.860 (2)°	0.40 × 0.35 × 0.30 mm
V = 1745.0 (5) Å³

Data collection top

Bruker APEX-II CCD diffractometer	7845 independent reflections
Radiation source: fine-focus sealed tube	6659 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
φ and ω scans	θ_max = 28.0°, θ_min = 1.1°
Absorption correction: multi-scan SADABS (Sheldrick, 2004)	h = −11→13
T_min = 0.928, T_max = 0.946	k = −13→13
26911 measured reflections	l = −24→24

Refinement top

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0418P)² + 0.9075P] where P = (F_o² + 2F_c²)/3
7845 reflections	(Δ/σ)_max < 0.001
429 parameters	Δρ_max = 0.39 e Å⁻³
2 restraints	Δρ_min = −0.39 e Å⁻³

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.36725 (18)	0.50983 (18)	0.37040 (9)	0.0222 (3)
C2	0.27153 (19)	0.50361 (19)	0.42932 (9)	0.0269 (4)
H2	0.1641	0.5553	0.4279	0.032*
C3	0.3364 (2)	0.42014 (19)	0.49035 (9)	0.0267 (4)
H3	0.2723	0.4140	0.5314	0.032*
C4	0.49335 (19)	0.34488 (18)	0.49317 (8)	0.0235 (3)
H4	0.5375	0.2878	0.5354	0.028*
C5	0.58277 (17)	0.35580 (17)	0.43266 (8)	0.0191 (3)
C6	0.52536 (17)	0.43714 (17)	0.36951 (8)	0.0177 (3)
C7	0.62929 (16)	0.43744 (17)	0.30371 (8)	0.0174 (3)
C8	0.92667 (17)	0.52223 (18)	0.27516 (9)	0.0223 (3)
H8A	1.0393	0.4733	0.2687	0.027*
H8B	0.8927	0.4514	0.3025	0.027*
C9	0.8793 (2)	0.6464 (2)	0.31835 (9)	0.0283 (4)
H9A	0.9155	0.7156	0.2927	0.042*
H9B	0.9238	0.6090	0.3642	0.042*
H9C	0.7680	0.6946	0.3259	0.042*
C10	0.96724 (18)	0.58297 (19)	0.14447 (9)	0.0243 (3)
H10A	0.9149	0.6071	0.1005	0.029*
H10B	1.0593	0.4900	0.1413	0.029*
C11	1.01599 (19)	0.6988 (2)	0.14853 (9)	0.0282 (4)
H11A	0.9255	0.7902	0.1543	0.042*
H11B	1.0763	0.7102	0.1048	0.042*
H11C	1.0776	0.6707	0.1891	0.042*
C12	0.81481 (17)	0.36645 (17)	0.12556 (8)	0.0205 (3)
H12A	0.7740	0.2955	0.1434	0.025*
H12B	0.8989	0.3456	0.1547	0.025*
C13	0.8768 (2)	0.3491 (2)	0.04897 (9)	0.0313 (4)
H13A	0.7959	0.3616	0.0207	0.047*
H13B	0.9614	0.2527	0.0464	0.047*
H13C	0.9133	0.4220	0.0304	0.047*
C14	0.55368 (18)	0.55841 (18)	0.09716 (9)	0.0231 (3)
H14A	0.5819	0.5512	0.0459	0.028*
H14B	0.4857	0.6609	0.1025	0.028*
C15	0.4669 (2)	0.4705 (2)	0.12475 (12)	0.0415 (5)
H15A	0.5312	0.3697	0.1172	0.062*
H15B	0.3746	0.5084	0.0994	0.062*
H15C	0.4388	0.4766	0.1755	0.062*
C16	0.2397 (2)	0.9663 (2)	0.09606 (9)	0.0281 (4)
C17	0.2472 (2)	0.9474 (2)	0.02632 (10)	0.0377 (5)
H17	0.2260	0.8748	0.0141	0.045*
C18	0.2864 (2)	1.0363 (2)	−0.02542 (10)	0.0374 (5)
H18	0.2928	1.0245	−0.0738	0.045*
C19	0.3162 (2)	1.1420 (2)	−0.00787 (9)	0.0327 (4)
H19	0.3440	1.2027	−0.0435	0.039*
C20	0.30468 (18)	1.15756 (19)	0.06270 (9)	0.0249 (3)
C21	0.26684 (17)	1.07181 (17)	0.11688 (8)	0.0188 (3)
C22	0.25296 (16)	1.09563 (17)	0.19325 (8)	0.0178 (3)
C23	0.12535 (18)	0.94247 (19)	0.38934 (9)	0.0241 (3)
H23A	0.0494	0.9807	0.4293	0.029*
H23B	0.1985	0.8429	0.4061	0.029*
C24	0.0443 (2)	0.9380 (2)	0.32910 (11)	0.0330 (4)
H24A	−0.0255	1.0365	0.3109	0.050*
H24B	−0.0134	0.8823	0.3466	0.050*
H24C	0.1197	0.8924	0.2910	0.050*
C25	0.11302 (17)	1.18718 (17)	0.37192 (8)	0.0200 (3)
H25A	0.0157	1.2162	0.3513	0.024*
H25B	0.1654	1.2411	0.3424	0.024*
C26	0.07895 (18)	1.22901 (19)	0.44651 (9)	0.0251 (3)
H26A	0.0305	1.1734	0.4766	0.038*
H26B	0.0102	1.3322	0.4452	0.038*
H26C	0.1742	1.2084	0.4659	0.038*
C27	0.50288 (18)	1.14751 (18)	0.26613 (8)	0.0212 (3)
H27A	0.5166	1.2241	0.2833	0.025*
H27B	0.4208	1.1951	0.2331	0.025*
C28	0.65006 (19)	1.0544 (2)	0.22560 (9)	0.0271 (4)
H28A	0.7335	1.0114	0.2570	0.041*
H28B	0.6732	1.1142	0.1851	0.041*
H28C	0.6381	0.9777	0.2086	0.041*
C29	0.48855 (18)	1.07665 (19)	0.39727 (8)	0.0225 (3)
H29A	0.4463	1.0224	0.4337	0.027*
H29B	0.4368	1.1789	0.4060	0.027*
C30	0.65814 (18)	1.01798 (19)	0.40554 (9)	0.0249 (3)
H30A	0.7100	0.9160	0.3982	0.037*
H30B	0.6729	1.0276	0.4533	0.037*
H30C	0.7005	1.0725	0.3704	0.037*
N1	0.61078 (14)	0.57026 (14)	0.27235 (7)	0.0171 (3)
H1N	0.5531 (17)	0.6437 (14)	0.2944 (9)	0.021*
N2	0.86543 (14)	0.56526 (15)	0.20521 (7)	0.0189 (3)
N3	0.69355 (14)	0.51275 (14)	0.13357 (7)	0.0180 (3)
N4	0.35276 (14)	0.98215 (14)	0.23445 (7)	0.0165 (3)
H4N	0.4223 (16)	0.9119 (15)	0.2137 (9)	0.020*
N5	0.20814 (14)	1.03206 (14)	0.36923 (7)	0.0177 (3)
N6	0.45443 (14)	1.06710 (14)	0.32700 (7)	0.0183 (3)
O1	0.72094 (12)	0.32468 (12)	0.28206 (6)	0.0228 (2)
O2	0.59113 (12)	0.76509 (12)	0.17011 (6)	0.0199 (2)
O3	0.16060 (13)	1.20949 (12)	0.21337 (6)	0.0245 (3)
O4	0.45592 (12)	0.80999 (12)	0.34521 (5)	0.0186 (2)
F1	0.30436 (11)	0.58847 (12)	0.30978 (5)	0.0313 (2)
F2	0.73617 (10)	0.28522 (11)	0.43493 (5)	0.0266 (2)
F3	0.20325 (15)	0.87869 (13)	0.14729 (6)	0.0432 (3)
F4	0.33580 (13)	1.26003 (13)	0.08068 (6)	0.0384 (3)
P1	0.68900 (4)	0.61027 (4)	0.19235 (2)	0.01603 (10)
P2	0.37136 (4)	0.96644 (4)	0.32203 (2)	0.01492 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0241 (7)	0.0228 (9)	0.0202 (8)	−0.0111 (7)	−0.0022 (6)	−0.0009 (6)
C2	0.0225 (8)	0.0293 (10)	0.0290 (9)	−0.0122 (7)	0.0056 (7)	−0.0077 (7)
C3	0.0343 (9)	0.0293 (10)	0.0222 (8)	−0.0206 (8)	0.0085 (7)	−0.0075 (7)
C4	0.0362 (9)	0.0242 (9)	0.0151 (8)	−0.0175 (7)	−0.0023 (6)	−0.0022 (6)
C5	0.0233 (7)	0.0191 (8)	0.0181 (8)	−0.0115 (6)	−0.0029 (6)	−0.0027 (6)
C6	0.0224 (7)	0.0169 (8)	0.0160 (7)	−0.0108 (6)	0.0015 (6)	−0.0038 (6)
C7	0.0191 (7)	0.0192 (8)	0.0154 (7)	−0.0096 (6)	−0.0019 (6)	−0.0020 (6)
C8	0.0216 (7)	0.0227 (9)	0.0217 (8)	−0.0100 (7)	−0.0053 (6)	0.0031 (7)
C9	0.0317 (9)	0.0364 (10)	0.0223 (9)	−0.0188 (8)	−0.0031 (7)	−0.0055 (7)
C10	0.0231 (7)	0.0316 (10)	0.0215 (8)	−0.0158 (7)	0.0054 (6)	−0.0067 (7)
C11	0.0285 (8)	0.0330 (10)	0.0279 (9)	−0.0196 (8)	0.0043 (7)	−0.0040 (8)
C12	0.0224 (7)	0.0177 (8)	0.0209 (8)	−0.0078 (6)	0.0003 (6)	−0.0059 (6)
C13	0.0322 (9)	0.0344 (10)	0.0230 (9)	−0.0098 (8)	0.0039 (7)	−0.0123 (8)
C14	0.0227 (7)	0.0240 (9)	0.0215 (8)	−0.0077 (7)	−0.0047 (6)	−0.0049 (7)
C15	0.0364 (10)	0.0485 (13)	0.0491 (13)	−0.0273 (10)	−0.0150 (9)	0.0046 (10)
C16	0.0372 (9)	0.0265 (9)	0.0233 (9)	−0.0161 (8)	−0.0065 (7)	−0.0008 (7)
C17	0.0511 (11)	0.0352 (11)	0.0292 (10)	−0.0165 (9)	−0.0129 (9)	−0.0093 (8)
C18	0.0377 (10)	0.0445 (12)	0.0172 (9)	−0.0044 (9)	−0.0067 (7)	−0.0080 (8)
C19	0.0290 (9)	0.0413 (11)	0.0182 (8)	−0.0102 (8)	−0.0003 (7)	0.0036 (8)
C20	0.0237 (8)	0.0267 (9)	0.0224 (8)	−0.0106 (7)	−0.0029 (6)	0.0011 (7)
C21	0.0193 (7)	0.0193 (8)	0.0155 (7)	−0.0066 (6)	−0.0031 (6)	−0.0004 (6)
C22	0.0192 (7)	0.0199 (8)	0.0157 (7)	−0.0104 (6)	−0.0025 (6)	0.0008 (6)
C23	0.0227 (7)	0.0232 (9)	0.0274 (9)	−0.0134 (7)	0.0050 (6)	−0.0020 (7)
C24	0.0268 (8)	0.0357 (11)	0.0443 (11)	−0.0200 (8)	0.0013 (8)	−0.0098 (9)
C25	0.0191 (7)	0.0183 (8)	0.0190 (8)	−0.0058 (6)	0.0011 (6)	−0.0026 (6)
C26	0.0238 (8)	0.0241 (9)	0.0233 (8)	−0.0072 (7)	0.0028 (6)	−0.0062 (7)
C27	0.0279 (8)	0.0208 (8)	0.0191 (8)	−0.0152 (7)	−0.0014 (6)	−0.0003 (6)
C28	0.0313 (8)	0.0361 (10)	0.0206 (8)	−0.0223 (8)	0.0057 (7)	−0.0054 (7)
C29	0.0243 (8)	0.0308 (9)	0.0167 (8)	−0.0148 (7)	0.0006 (6)	−0.0074 (7)
C30	0.0245 (8)	0.0282 (9)	0.0234 (8)	−0.0119 (7)	−0.0040 (6)	−0.0043 (7)
N1	0.0203 (6)	0.0154 (7)	0.0149 (6)	−0.0078 (5)	0.0019 (5)	−0.0033 (5)
N2	0.0201 (6)	0.0223 (7)	0.0165 (6)	−0.0118 (5)	0.0014 (5)	−0.0032 (5)
N3	0.0189 (6)	0.0175 (7)	0.0165 (6)	−0.0066 (5)	−0.0011 (5)	−0.0035 (5)
N4	0.0191 (6)	0.0161 (7)	0.0132 (6)	−0.0070 (5)	−0.0002 (5)	−0.0024 (5)
N5	0.0182 (6)	0.0163 (7)	0.0177 (6)	−0.0080 (5)	0.0024 (5)	−0.0020 (5)
N6	0.0216 (6)	0.0233 (7)	0.0140 (6)	−0.0131 (5)	0.0006 (5)	−0.0042 (5)
O1	0.0262 (6)	0.0170 (6)	0.0224 (6)	−0.0087 (5)	0.0039 (5)	−0.0031 (5)
O2	0.0230 (5)	0.0173 (6)	0.0169 (5)	−0.0081 (5)	0.0025 (4)	−0.0013 (4)
O3	0.0257 (6)	0.0207 (6)	0.0204 (6)	−0.0039 (5)	−0.0031 (4)	−0.0031 (5)
O4	0.0222 (5)	0.0169 (6)	0.0144 (5)	−0.0071 (4)	−0.0006 (4)	−0.0016 (4)
F1	0.0239 (5)	0.0356 (6)	0.0264 (5)	−0.0089 (4)	−0.0057 (4)	0.0063 (4)
F2	0.0233 (5)	0.0304 (6)	0.0250 (5)	−0.0113 (4)	−0.0063 (4)	0.0012 (4)
F3	0.0746 (8)	0.0430 (7)	0.0328 (6)	−0.0446 (7)	−0.0103 (6)	0.0027 (5)
F4	0.0549 (7)	0.0427 (7)	0.0309 (6)	−0.0362 (6)	−0.0027 (5)	0.0042 (5)
P1	0.01849 (18)	0.0158 (2)	0.01376 (19)	−0.00829 (15)	0.00112 (14)	−0.00177 (15)
P2	0.01601 (17)	0.0156 (2)	0.01290 (19)	−0.00705 (15)	−0.00050 (13)	−0.00145 (15)

Geometric parameters (Å, º) top

C1—F1	1.3536 (19)	C18—C19	1.376 (3)
C1—C2	1.379 (2)	C18—H18	0.9500
C1—C6	1.392 (2)	C19—C20	1.377 (2)
C2—C3	1.379 (3)	C19—H19	0.9500
C2—H2	0.9500	C20—F4	1.355 (2)
C3—C4	1.388 (2)	C20—C21	1.378 (2)
C3—H3	0.9500	C21—C22	1.509 (2)
C4—C5	1.376 (2)	C22—O3	1.2154 (19)
C4—H4	0.9500	C22—N4	1.3585 (19)
C5—F2	1.3551 (18)	C23—N5	1.4791 (19)
C5—C6	1.386 (2)	C23—C24	1.520 (3)
C6—C7	1.510 (2)	C23—H23A	0.9900
C7—O1	1.2172 (19)	C23—H23B	0.9900
C7—N1	1.359 (2)	C24—H24A	0.9800
C8—N2	1.468 (2)	C24—H24B	0.9800
C8—C9	1.523 (2)	C24—H24C	0.9800
C8—H8A	0.9900	C25—N5	1.469 (2)
C8—H8B	0.9900	C25—C26	1.520 (2)
C9—H9A	0.9800	C25—H25A	0.9900
C9—H9B	0.9800	C25—H25B	0.9900
C9—H9C	0.9800	C26—H26A	0.9800
C10—N2	1.4708 (19)	C26—H26B	0.9800
C10—C11	1.516 (2)	C26—H26C	0.9800
C10—H10A	0.9900	C27—N6	1.4730 (19)
C10—H10B	0.9900	C27—C28	1.523 (2)
C11—H11A	0.9800	C27—H27A	0.9900
C11—H11B	0.9800	C27—H27B	0.9900
C11—H11C	0.9800	C28—H28A	0.9800
C12—N3	1.474 (2)	C28—H28B	0.9800
C12—C13	1.519 (2)	C28—H28C	0.9800
C12—H12A	0.9900	C29—N6	1.470 (2)
C12—H12B	0.9900	C29—C30	1.523 (2)
C13—H13A	0.9800	C29—H29A	0.9900
C13—H13B	0.9800	C29—H29B	0.9900
C13—H13C	0.9800	C30—H30A	0.9800
C14—N3	1.4814 (19)	C30—H30B	0.9800
C14—C15	1.512 (2)	C30—H30C	0.9800
C14—H14A	0.9900	N1—P1	1.6919 (13)
C14—H14B	0.9900	N1—H1N	0.862 (9)
C15—H15A	0.9800	N2—P1	1.6320 (13)
C15—H15B	0.9800	N3—P1	1.6369 (13)
C15—H15C	0.9800	N4—P2	1.6918 (13)
C16—F3	1.352 (2)	N4—H4N	0.859 (9)
C16—C17	1.376 (3)	N5—P2	1.6378 (13)
C16—C21	1.385 (2)	N6—P2	1.6288 (13)
C17—C18	1.379 (3)	O2—P1	1.4845 (12)
C17—H17	0.9500	O4—P2	1.4816 (12)

F1—C1—C2	118.38 (14)	C20—C21—C16	115.50 (15)
F1—C1—C6	118.15 (14)	C20—C21—C22	121.32 (14)
C2—C1—C6	123.47 (15)	C16—C21—C22	123.16 (14)
C1—C2—C3	118.02 (15)	O3—C22—N4	125.12 (14)
C1—C2—H2	121.0	O3—C22—C21	120.69 (14)
C3—C2—H2	121.0	N4—C22—C21	114.18 (13)
C2—C3—C4	121.51 (15)	N5—C23—C24	113.50 (14)
C2—C3—H3	119.2	N5—C23—H23A	108.9
C4—C3—H3	119.2	C24—C23—H23A	108.9
C5—C4—C3	117.68 (15)	N5—C23—H23B	108.9
C5—C4—H4	121.2	C24—C23—H23B	108.9
C3—C4—H4	121.2	H23A—C23—H23B	107.7
F2—C5—C4	118.41 (14)	C23—C24—H24A	109.5
F2—C5—C6	117.69 (13)	C23—C24—H24B	109.5
C4—C5—C6	123.88 (15)	H24A—C24—H24B	109.5
C5—C6—C1	115.43 (14)	C23—C24—H24C	109.5
C5—C6—C7	121.28 (13)	H24A—C24—H24C	109.5
C1—C6—C7	123.18 (14)	H24B—C24—H24C	109.5
O1—C7—N1	124.48 (14)	N5—C25—C26	113.31 (13)
O1—C7—C6	120.57 (14)	N5—C25—H25A	108.9
N1—C7—C6	114.94 (13)	C26—C25—H25A	108.9
N2—C8—C9	114.42 (14)	N5—C25—H25B	108.9
N2—C8—H8A	108.7	C26—C25—H25B	108.9
C9—C8—H8A	108.7	H25A—C25—H25B	107.7
N2—C8—H8B	108.7	C25—C26—H26A	109.5
C9—C8—H8B	108.7	C25—C26—H26B	109.5
H8A—C8—H8B	107.6	H26A—C26—H26B	109.5
C8—C9—H9A	109.5	C25—C26—H26C	109.5
C8—C9—H9B	109.5	H26A—C26—H26C	109.5
H9A—C9—H9B	109.5	H26B—C26—H26C	109.5
C8—C9—H9C	109.5	N6—C27—C28	114.02 (14)
H9A—C9—H9C	109.5	N6—C27—H27A	108.7
H9B—C9—H9C	109.5	C28—C27—H27A	108.7
N2—C10—C11	113.87 (13)	N6—C27—H27B	108.7
N2—C10—H10A	108.8	C28—C27—H27B	108.7
C11—C10—H10A	108.8	H27A—C27—H27B	107.6
N2—C10—H10B	108.8	C27—C28—H28A	109.5
C11—C10—H10B	108.8	C27—C28—H28B	109.5
H10A—C10—H10B	107.7	H28A—C28—H28B	109.5
C10—C11—H11A	109.5	C27—C28—H28C	109.5
C10—C11—H11B	109.5	H28A—C28—H28C	109.5
H11A—C11—H11B	109.5	H28B—C28—H28C	109.5
C10—C11—H11C	109.5	N6—C29—C30	113.61 (13)
H11A—C11—H11C	109.5	N6—C29—H29A	108.8
H11B—C11—H11C	109.5	C30—C29—H29A	108.8
N3—C12—C13	112.16 (14)	N6—C29—H29B	108.8
N3—C12—H12A	109.2	C30—C29—H29B	108.8
C13—C12—H12A	109.2	H29A—C29—H29B	107.7
N3—C12—H12B	109.2	C29—C30—H30A	109.5
C13—C12—H12B	109.2	C29—C30—H30B	109.5
H12A—C12—H12B	107.9	H30A—C30—H30B	109.5
C12—C13—H13A	109.5	C29—C30—H30C	109.5
C12—C13—H13B	109.5	H30A—C30—H30C	109.5
H13A—C13—H13B	109.5	H30B—C30—H30C	109.5
C12—C13—H13C	109.5	C7—N1—P1	126.89 (11)
H13A—C13—H13C	109.5	C7—N1—H1N	118.5 (12)
H13B—C13—H13C	109.5	P1—N1—H1N	114.6 (12)
N3—C14—C15	113.90 (14)	C8—N2—C10	116.67 (12)
N3—C14—H14A	108.8	C8—N2—P1	124.21 (10)
C15—C14—H14A	108.8	C10—N2—P1	118.78 (11)
N3—C14—H14B	108.8	C12—N3—C14	116.44 (12)
C15—C14—H14B	108.8	C12—N3—P1	123.86 (10)
H14A—C14—H14B	107.7	C14—N3—P1	118.29 (10)
C14—C15—H15A	109.5	C22—N4—P2	128.35 (11)
C14—C15—H15B	109.5	C22—N4—H4N	117.5 (12)
H15A—C15—H15B	109.5	P2—N4—H4N	113.8 (12)
C14—C15—H15C	109.5	C25—N5—C23	114.57 (12)
H15A—C15—H15C	109.5	C25—N5—P2	123.35 (10)
H15B—C15—H15C	109.5	C23—N5—P2	118.53 (11)
F3—C16—C17	118.90 (16)	C29—N6—C27	116.48 (12)
F3—C16—C21	117.75 (15)	C29—N6—P2	118.25 (10)
C17—C16—C21	123.34 (17)	C27—N6—P2	125.25 (10)
C16—C17—C18	118.34 (18)	O2—P1—N2	116.97 (7)
C16—C17—H17	120.8	O2—P1—N3	109.95 (7)
C18—C17—H17	120.8	N2—P1—N3	106.97 (7)
C19—C18—C17	120.89 (17)	O2—P1—N1	105.64 (6)
C19—C18—H18	119.6	N2—P1—N1	105.14 (7)
C17—C18—H18	119.6	N3—P1—N1	112.19 (7)
C18—C19—C20	118.29 (17)	O4—P2—N6	117.09 (7)
C18—C19—H19	120.9	O4—P2—N5	109.45 (6)
C20—C19—H19	120.9	N6—P2—N5	106.67 (7)
F4—C20—C19	118.80 (15)	O4—P2—N4	106.03 (6)
F4—C20—C21	117.56 (15)	N6—P2—N4	104.30 (6)
C19—C20—C21	123.62 (17)	N5—P2—N4	113.43 (7)

F1—C1—C2—C3	178.31 (15)	C13—C12—N3—P1	−131.07 (13)
C6—C1—C2—C3	−0.4 (3)	C15—C14—N3—C12	64.02 (19)
C1—C2—C3—C4	0.4 (3)	C15—C14—N3—P1	−102.97 (16)
C2—C3—C4—C5	−0.2 (2)	O3—C22—N4—P2	2.2 (2)
C3—C4—C5—F2	178.75 (14)	C21—C22—N4—P2	−179.21 (10)
C3—C4—C5—C6	0.0 (2)	C26—C25—N5—C23	78.67 (16)
F2—C5—C6—C1	−178.73 (13)	C26—C25—N5—P2	−122.95 (13)
C4—C5—C6—C1	0.0 (2)	C24—C23—N5—C25	82.79 (17)
F2—C5—C6—C7	5.0 (2)	C24—C23—N5—P2	−76.70 (17)
C4—C5—C6—C7	−176.22 (14)	C30—C29—N6—C27	−61.26 (19)
F1—C1—C6—C5	−178.52 (14)	C30—C29—N6—P2	117.10 (13)
C2—C1—C6—C5	0.2 (2)	C28—C27—N6—C29	100.51 (16)
F1—C1—C6—C7	−2.4 (2)	C28—C27—N6—P2	−77.73 (16)
C2—C1—C6—C7	176.33 (15)	C8—N2—P1—O2	108.18 (13)
C5—C6—C7—O1	53.3 (2)	C10—N2—P1—O2	−64.95 (13)
C1—C6—C7—O1	−122.68 (17)	C8—N2—P1—N3	−128.08 (13)
C5—C6—C7—N1	−126.92 (15)	C10—N2—P1—N3	58.79 (13)
C1—C6—C7—N1	57.1 (2)	C8—N2—P1—N1	−8.64 (14)
F3—C16—C17—C18	−179.22 (17)	C10—N2—P1—N1	178.24 (12)
C21—C16—C17—C18	1.1 (3)	C12—N3—P1—O2	158.74 (11)
C16—C17—C18—C19	−0.4 (3)	C14—N3—P1—O2	−35.31 (13)
C17—C18—C19—C20	−0.6 (3)	C12—N3—P1—N2	30.77 (13)
C18—C19—C20—F4	179.12 (16)	C14—N3—P1—N2	−163.28 (11)
C18—C19—C20—C21	0.9 (3)	C12—N3—P1—N1	−84.02 (13)
F4—C20—C21—C16	−178.46 (14)	C14—N3—P1—N1	81.93 (12)
C19—C20—C21—C16	−0.2 (2)	C7—N1—P1—O2	158.35 (12)
F4—C20—C21—C22	2.9 (2)	C7—N1—P1—N2	−77.34 (14)
C19—C20—C21—C22	−178.81 (15)	C7—N1—P1—N3	38.56 (15)
F3—C16—C21—C20	179.52 (15)	C29—N6—P2—O4	−62.89 (13)
C17—C16—C21—C20	−0.8 (3)	C27—N6—P2—O4	115.31 (13)
F3—C16—C21—C22	−1.9 (2)	C29—N6—P2—N5	60.04 (13)
C17—C16—C21—C22	177.75 (17)	C27—N6—P2—N5	−121.76 (13)
C20—C21—C22—O3	60.4 (2)	C29—N6—P2—N4	−179.66 (11)
C16—C21—C22—O3	−118.08 (18)	C27—N6—P2—N4	−1.46 (14)
C20—C21—C22—N4	−118.26 (16)	C25—N5—P2—O4	165.15 (11)
C16—C21—C22—N4	63.24 (19)	C23—N5—P2—O4	−37.27 (13)
O1—C7—N1—P1	9.5 (2)	C25—N5—P2—N6	37.57 (14)
C6—C7—N1—P1	−170.31 (10)	C23—N5—P2—N6	−164.85 (11)
C9—C8—N2—C10	98.29 (16)	C25—N5—P2—N4	−76.67 (13)
C9—C8—N2—P1	−74.97 (16)	C23—N5—P2—N4	80.91 (13)
C11—C10—N2—C8	−61.34 (19)	C22—N4—P2—O4	161.18 (12)
C11—C10—N2—P1	112.30 (14)	C22—N4—P2—N6	−74.62 (14)
C13—C12—N3—C14	62.74 (17)	C22—N4—P2—N5	41.03 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4N···O2	0.86 (1)	1.89 (1)	2.7429 (17)	173 (2)
N1—H1N···O4	0.86 (1)	1.93 (1)	2.7828 (17)	170 (2)
C4—H4···O4ⁱ	0.95	2.34	3.238 (2)	157
C19—H19···O2ⁱⁱ	0.95	2.43	3.230 (2)	142
C27—H27A···O1ⁱⁱⁱ	0.99	2.67	3.5023 (19)	142
C27—H27B···O3	0.99	2.59	3.418 (2)	141

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

(II) top

Crystal data top

C₁₃H₂₀F₂N₃O₃P	D_x = 1.382 Mg m⁻³
M_r = 335.29	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 2764 reflections
a = 8.7127 (4) Å	θ = 4.8–64.9°
b = 10.9675 (8) Å	µ = 1.86 mm⁻¹
c = 16.8649 (9) Å	T = 100 K
V = 1611.55 (16) Å³	BLOCK, colourless
Z = 4	0.15 × 0.10 × 0.08 mm
F(000) = 704

Data collection top

Bruker APEX-II CCD diffractometer	2606 independent reflections
Radiation source: fine-focus sealed tube	2204 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
φ and ω scans	θ_max = 65.2°, θ_min = 4.8°
Absorption correction: multi-scan SADABS (Sheldrick, 2004)	h = −10→9
T_min = 0.768, T_max = 0.866	k = −12→12
5564 measured reflections	l = −16→19

Refinement top

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)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.112	w = 1/[σ²(F_o²) + (0.0637P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2606 reflections	Δρ_max = 0.23 e Å⁻³
213 parameters	Δρ_min = −0.28 e Å⁻³
4 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (4)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
P1	0.31120 (8)	0.24796 (10)	0.43973 (5)	0.0243 (2)
F1	0.4534 (3)	0.6434 (2)	0.44471 (12)	0.0450 (6)
F2	0.4502 (2)	0.4419 (2)	0.68872 (11)	0.0351 (5)
O1	0.2008 (2)	0.4597 (2)	0.53800 (13)	0.0285 (6)
O1S	−0.1085 (3)	0.3996 (4)	0.37612 (16)	0.0485 (8)
H1S	−0.148 (5)	0.380 (4)	0.4213 (14)	0.058*
O2	0.2260 (2)	0.1668 (2)	0.49445 (13)	0.0294 (6)
N1	0.4083 (3)	0.3550 (3)	0.49294 (16)	0.0255 (7)
H1N	0.5075 (12)	0.355 (3)	0.493 (2)	0.031*
N2	0.2082 (3)	0.3171 (3)	0.37509 (16)	0.0286 (7)
H2N	0.1130 (16)	0.331 (3)	0.386 (2)	0.034*
N3	0.4444 (3)	0.1823 (3)	0.38705 (16)	0.0238 (7)
H3N	0.506 (3)	0.135 (3)	0.4133 (19)	0.029*
C1	0.4990 (4)	0.6377 (4)	0.5217 (2)	0.0341 (9)
C1S	−0.0844 (5)	0.5129 (5)	0.3951 (3)	0.0557 (13)
H1D	−0.0446	0.5570	0.3489	0.083*
H1E	−0.0094	0.5169	0.4383	0.083*
H1C	−0.1810	0.5502	0.4123	0.083*
C2	0.5931 (4)	0.7279 (4)	0.5509 (2)	0.0443 (11)
H2A	0.6268	0.7931	0.5181	0.053*
C3	0.6371 (4)	0.7204 (4)	0.6295 (3)	0.0404 (11)
H3A	0.7010	0.7821	0.6512	0.048*
C4	0.5900 (4)	0.6248 (4)	0.6773 (2)	0.0338 (9)
H4A	0.6203	0.6199	0.7313	0.041*
C5	0.4979 (4)	0.5375 (4)	0.6437 (2)	0.0260 (8)
C6	0.4477 (3)	0.5408 (3)	0.56596 (19)	0.0242 (7)
C7	0.3397 (3)	0.4482 (4)	0.53180 (18)	0.0244 (8)
C8	0.2847 (4)	0.3867 (3)	0.31132 (19)	0.0277 (8)
H8A	0.3424	0.4556	0.3348	0.033*
H8B	0.2062	0.4208	0.2751	0.033*
C9	0.3944 (4)	0.3058 (3)	0.2645 (2)	0.0244 (8)
C10	0.5147 (3)	0.2520 (4)	0.32041 (18)	0.0241 (7)
H10A	0.5832	0.1972	0.2900	0.029*
H10B	0.5782	0.3189	0.3423	0.029*
C11	0.3066 (4)	0.2048 (3)	0.22205 (19)	0.0294 (8)
H11A	0.2340	0.2410	0.1845	0.044*
H11B	0.2504	0.1559	0.2611	0.044*
H11C	0.3791	0.1526	0.1934	0.044*
C12	0.4755 (4)	0.3854 (4)	0.2035 (2)	0.0323 (9)
H12A	0.3992	0.4231	0.1686	0.048*
H12B	0.5456	0.3351	0.1720	0.048*
H12C	0.5339	0.4492	0.2308	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0110 (3)	0.0431 (5)	0.0187 (4)	0.0022 (4)	0.0000 (3)	−0.0051 (4)
F1	0.0471 (12)	0.0654 (16)	0.0224 (11)	−0.0139 (12)	−0.0014 (10)	0.0102 (12)
F2	0.0370 (11)	0.0458 (14)	0.0225 (11)	0.0038 (11)	−0.0053 (9)	0.0027 (10)
O1	0.0132 (10)	0.0473 (15)	0.0249 (13)	0.0013 (11)	0.0033 (9)	−0.0073 (12)
O1S	0.0302 (15)	0.085 (3)	0.0300 (16)	0.0090 (17)	0.0043 (13)	0.0054 (18)
O2	0.0159 (11)	0.0503 (17)	0.0222 (12)	−0.0031 (11)	−0.0001 (9)	−0.0024 (11)
N1	0.0118 (12)	0.0420 (18)	0.0226 (15)	0.0046 (13)	−0.0004 (11)	−0.0048 (14)
N2	0.0140 (12)	0.053 (2)	0.0191 (15)	0.0068 (14)	−0.0001 (12)	−0.0068 (14)
N3	0.0155 (13)	0.0371 (18)	0.0187 (15)	0.0028 (13)	0.0008 (11)	0.0004 (14)
C1	0.0241 (17)	0.058 (3)	0.0199 (19)	−0.0034 (18)	0.0016 (15)	0.001 (2)
C1S	0.038 (2)	0.076 (4)	0.053 (3)	0.007 (3)	−0.004 (2)	0.018 (3)
C2	0.035 (2)	0.054 (3)	0.043 (2)	−0.015 (2)	−0.0015 (18)	0.006 (2)
C3	0.0254 (17)	0.048 (3)	0.048 (2)	−0.0083 (18)	−0.0028 (18)	−0.012 (2)
C4	0.0191 (17)	0.054 (3)	0.028 (2)	0.0075 (18)	−0.0043 (15)	−0.0066 (19)
C5	0.0166 (15)	0.038 (2)	0.0238 (18)	0.0042 (16)	0.0026 (13)	0.0012 (18)
C6	0.0150 (14)	0.040 (2)	0.0175 (17)	0.0020 (15)	0.0034 (14)	−0.0025 (17)
C7	0.0163 (16)	0.043 (2)	0.0135 (16)	0.0031 (15)	0.0028 (12)	0.0010 (17)
C8	0.0197 (17)	0.040 (2)	0.0237 (18)	0.0057 (16)	−0.0040 (14)	−0.0047 (16)
C9	0.0169 (15)	0.037 (2)	0.0188 (17)	0.0020 (15)	−0.0011 (14)	0.0016 (16)
C10	0.0158 (14)	0.0356 (19)	0.0210 (17)	0.0020 (17)	0.0004 (12)	−0.0034 (19)
C11	0.0234 (16)	0.044 (2)	0.0207 (18)	0.0000 (17)	0.0002 (15)	−0.0041 (16)
C12	0.0253 (18)	0.038 (2)	0.033 (2)	−0.0014 (17)	0.0046 (16)	0.0033 (19)

Geometric parameters (Å, º) top

P1—O2	1.481 (3)	C2—H2A	0.9500
P1—N2	1.603 (3)	C3—C4	1.385 (6)
P1—N3	1.629 (3)	C3—H3A	0.9500
P1—N1	1.703 (3)	C4—C5	1.372 (5)
F1—C1	1.359 (4)	C4—H4A	0.9500
F2—C5	1.359 (4)	C5—C6	1.383 (5)
O1—C7	1.221 (4)	C6—C7	1.499 (5)
O1S—C1S	1.300 (6)	C8—C9	1.524 (5)
O1S—H1S	0.863 (10)	C8—H8A	0.9900
N1—C7	1.354 (4)	C8—H8B	0.9900
N1—H1N	0.864 (10)	C9—C12	1.523 (5)
N2—C8	1.478 (4)	C9—C11	1.524 (5)
N2—H2N	0.862 (10)	C9—C10	1.529 (4)
N3—C10	1.491 (4)	C10—H10A	0.9900
N3—H3N	0.869 (10)	C10—H10B	0.9900
C1—C6	1.374 (5)	C11—H11A	0.9800
C1—C2	1.376 (5)	C11—H11B	0.9800
C1S—H1D	0.9800	C11—H11C	0.9800
C1S—H1E	0.9800	C12—H12A	0.9800
C1S—H1C	0.9800	C12—H12B	0.9800
C2—C3	1.382 (6)	C12—H12C	0.9800

O2—P1—N2	115.28 (14)	C1—C6—C5	115.6 (3)
O2—P1—N3	115.55 (16)	C1—C6—C7	121.3 (3)
N2—P1—N3	103.71 (15)	C5—C6—C7	123.0 (3)
O2—P1—N1	109.57 (14)	O1—C7—N1	123.9 (3)
N2—P1—N1	108.10 (16)	O1—C7—C6	121.3 (3)
N3—P1—N1	103.77 (14)	N1—C7—C6	114.8 (3)
C1S—O1S—H1S	95 (3)	N2—C8—C9	111.0 (3)
C7—N1—P1	123.8 (2)	N2—C8—H8A	109.4
C7—N1—H1N	116 (3)	C9—C8—H8A	109.4
P1—N1—H1N	120 (2)	N2—C8—H8B	109.4
C8—N2—P1	119.1 (2)	C9—C8—H8B	109.4
C8—N2—H2N	120 (3)	H8A—C8—H8B	108.0
P1—N2—H2N	119 (3)	C12—C9—C11	109.4 (3)
C10—N3—P1	118.5 (2)	C12—C9—C8	107.9 (3)
C10—N3—H3N	116 (2)	C11—C9—C8	110.6 (3)
P1—N3—H3N	115 (2)	C12—C9—C10	108.6 (3)
F1—C1—C6	117.3 (3)	C11—C9—C10	110.7 (3)
F1—C1—C2	118.9 (4)	C8—C9—C10	109.6 (3)
C6—C1—C2	123.7 (4)	N3—C10—C9	112.4 (2)
O1S—C1S—H1D	109.5	N3—C10—H10A	109.1
O1S—C1S—H1E	109.5	C9—C10—H10A	109.1
H1D—C1S—H1E	109.5	N3—C10—H10B	109.1
O1S—C1S—H1C	109.5	C9—C10—H10B	109.1
H1D—C1S—H1C	109.5	H10A—C10—H10B	107.9
H1E—C1S—H1C	109.5	C9—C11—H11A	109.5
C1—C2—C3	117.7 (4)	C9—C11—H11B	109.5
C1—C2—H2A	121.1	H11A—C11—H11B	109.5
C3—C2—H2A	121.1	C9—C11—H11C	109.5
C2—C3—C4	121.4 (4)	H11A—C11—H11C	109.5
C2—C3—H3A	119.3	H11B—C11—H11C	109.5
C4—C3—H3A	119.3	C9—C12—H12A	109.5
C5—C4—C3	117.5 (3)	C9—C12—H12B	109.5
C5—C4—H4A	121.3	H12A—C12—H12B	109.5
C3—C4—H4A	121.3	C9—C12—H12C	109.5
F2—C5—C4	119.1 (3)	H12A—C12—H12C	109.5
F2—C5—C6	116.9 (3)	H12B—C12—H12C	109.5
C4—C5—C6	123.9 (4)

O2—P1—N1—C7	−70.9 (3)	F2—C5—C6—C1	−179.4 (3)
N2—P1—N1—C7	55.4 (3)	C4—C5—C6—C1	1.4 (5)
N3—P1—N1—C7	165.1 (3)	F2—C5—C6—C7	2.8 (5)
O2—P1—N2—C8	−171.8 (2)	C4—C5—C6—C7	−176.3 (3)
N3—P1—N2—C8	−44.5 (3)	P1—N1—C7—O1	6.1 (5)
N1—P1—N2—C8	65.2 (3)	P1—N1—C7—C6	−172.4 (2)
O2—P1—N3—C10	168.8 (2)	C1—C6—C7—O1	−91.5 (4)
N2—P1—N3—C10	41.6 (3)	C5—C6—C7—O1	86.2 (4)
N1—P1—N3—C10	−71.3 (3)	C1—C6—C7—N1	87.0 (4)
F1—C1—C2—C3	179.6 (3)	C5—C6—C7—N1	−95.3 (4)
C6—C1—C2—C3	−0.5 (6)	P1—N2—C8—C9	56.6 (4)
C1—C2—C3—C4	0.8 (6)	N2—C8—C9—C12	−176.6 (3)
C2—C3—C4—C5	0.0 (6)	N2—C8—C9—C11	63.8 (3)
C3—C4—C5—F2	179.6 (3)	N2—C8—C9—C10	−58.5 (4)
C3—C4—C5—C6	−1.2 (5)	P1—N3—C10—C9	−51.6 (4)
F1—C1—C6—C5	179.3 (3)	C12—C9—C10—N3	174.4 (3)
C2—C1—C6—C5	−0.5 (5)	C11—C9—C10—N3	−65.5 (4)
F1—C1—C6—C7	−2.9 (5)	C8—C9—C10—N3	56.8 (4)
C2—C1—C6—C7	177.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1S—H1S···O2ⁱ	0.86 (1)	1.87 (2)	2.716 (4)	167 (4)
N1—H1N···O2ⁱⁱ	0.86 (1)	1.93 (1)	2.786 (3)	171 (4)
N2—H2N···O1S	0.86 (1)	2.08 (2)	2.904 (4)	160 (3)
N3—H3N···O1ⁱⁱ	0.87 (1)	2.15 (1)	3.003 (4)	166 (3)
C4—H4A···O1Sⁱⁱⁱ	0.95	2.45	3.368 (5)	161
C8—H8B···F2^iv	0.99	2.50	3.463 (4)	165

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

(III) top

Crystal data top

C₁₆H₁₈NO₄P	F(000) = 336
M_r = 319.28	D_x = 1.328 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 600 reflections
a = 6.4231 (2) Å	θ = 1–14°
b = 9.1119 (3) Å	µ = 0.19 mm⁻¹
c = 13.6799 (4) Å	T = 293 K
β = 94.137 (2)°	Block, colourless
V = 798.55 (4) Å³	0.3 × 0.25 × 0.19 mm
Z = 2

Data collection top

KappaCCD diffractometer	3194 independent reflections
Radiation source: Enraf Nonius FR590	2565 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
CCD rotation images, thick slices scans	h = −8→8
Absorption correction: multi-scan SADABS (Sheldrick, 2004)	k = −11→10
T_min = 0.941, T_max = 0.968	l = −17→17
6909 measured reflections

Refinement top

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)] = 0.043	H-atom parameters constrained
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.0512P)² + 0.0708P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.006
3194 reflections	Δρ_max = 0.16 e Å⁻³
199 parameters	Δρ_min = −0.21 e Å⁻³
1 restraint	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.09 (10)

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.2228 (4)	0.9014 (3)	0.61709 (17)	0.0474 (6)
C2	0.3714 (4)	0.9299 (3)	0.55152 (17)	0.0555 (6)
H2	0.5003	0.8831	0.5571	0.067*
C3	0.3229 (5)	1.0303 (4)	0.47717 (19)	0.0655 (8)
H3	0.4214	1.0514	0.4326	0.079*
C4	0.1348 (5)	1.0983 (4)	0.4683 (2)	0.0703 (9)
H4	0.1052	1.1655	0.418	0.084*
C5	−0.0135 (6)	1.0677 (4)	0.5342 (2)	0.0742 (9)
H5	−0.1433	1.1132	0.5274	0.089*
C6	0.0308 (4)	0.9699 (3)	0.6100 (2)	0.0596 (7)
H6	−0.0668	0.9506	0.6553	0.072*
C7	0.4687 (4)	0.5295 (3)	0.78227 (16)	0.0518 (6)
C8	0.6680 (5)	0.4773 (4)	0.7972 (2)	0.0647 (8)
H8	0.7693	0.5311	0.8337	0.078*
C9	0.7168 (6)	0.3428 (4)	0.7570 (3)	0.0833 (10)
H9	0.8515	0.3057	0.7672	0.1*
C10	0.5693 (8)	0.2648 (4)	0.7029 (3)	0.0875 (11)
H10	0.6034	0.1747	0.6765	0.105*
C11	0.3728 (6)	0.3181 (5)	0.6875 (2)	0.0824 (10)
H11	0.273	0.2643	0.6502	0.099*
C12	0.3185 (5)	0.4529 (4)	0.7271 (2)	0.0673 (8)
H12	0.1839	0.4898	0.7162	0.081*
C13	0.4307 (4)	1.0351 (3)	0.9151 (2)	0.0615 (7)
H13A	0.5444	1.0718	0.879	0.074*
H13B	0.4897	0.9932	0.9761	0.074*
C14	0.2880 (6)	1.1571 (4)	0.9359 (3)	0.0813 (9)
H14A	0.3635	1.2292	0.9768	0.098*
H14B	0.2406	1.2046	0.8749	0.098*
C15	0.1249 (5)	0.8751 (4)	0.9017 (3)	0.0796 (9)
H15A	0.1623	0.8189	0.9606	0.096*
H15B	0.0433	0.8123	0.8563	0.096*
C16	−0.0010 (5)	1.0032 (5)	0.9265 (3)	0.0897 (12)
H16A	−0.0564	1.0496	0.8663	0.108*
H16B	−0.1183	0.9699	0.9614	0.108*
N1	0.3152 (3)	0.9220 (3)	0.85728 (16)	0.0543 (5)
O1	0.2603 (3)	0.79354 (19)	0.68948 (11)	0.0538 (5)
O2	0.6307 (3)	0.8671 (2)	0.75590 (12)	0.0590 (5)
O3	0.4142 (3)	0.6600 (2)	0.82887 (11)	0.0592 (5)
O4	0.1120 (4)	1.1077 (3)	0.98403 (16)	0.0775 (6)
P1	0.42539 (9)	0.81767 (7)	0.78057 (4)	0.04627 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0561 (15)	0.0371 (13)	0.0482 (12)	−0.0006 (11)	−0.0012 (10)	−0.0043 (10)
C2	0.0641 (16)	0.0505 (15)	0.0523 (13)	0.0070 (13)	0.0082 (12)	−0.0022 (11)
C3	0.089 (2)	0.0569 (18)	0.0514 (14)	0.0081 (17)	0.0114 (14)	0.0048 (13)
C4	0.095 (2)	0.0570 (19)	0.0569 (17)	0.0137 (18)	−0.0072 (15)	0.0054 (14)
C5	0.0687 (19)	0.065 (2)	0.087 (2)	0.0187 (17)	−0.0129 (17)	−0.0019 (17)
C6	0.0525 (15)	0.0577 (17)	0.0687 (16)	−0.0033 (13)	0.0051 (12)	−0.0042 (13)
C7	0.0750 (17)	0.0407 (14)	0.0405 (12)	0.0026 (13)	0.0088 (11)	0.0044 (10)
C8	0.074 (2)	0.0557 (18)	0.0637 (15)	0.0050 (15)	−0.0026 (14)	0.0038 (14)
C9	0.095 (2)	0.064 (2)	0.092 (2)	0.024 (2)	0.0236 (19)	0.0105 (17)
C10	0.129 (3)	0.0487 (19)	0.090 (2)	−0.002 (2)	0.037 (2)	−0.0033 (16)
C11	0.114 (3)	0.065 (2)	0.0695 (17)	−0.029 (3)	0.0121 (17)	−0.0119 (19)
C12	0.075 (2)	0.065 (2)	0.0629 (16)	−0.0127 (16)	0.0066 (14)	0.0014 (15)
C13	0.0605 (16)	0.0595 (17)	0.0646 (14)	−0.0058 (14)	0.0050 (12)	−0.0111 (13)
C14	0.091 (2)	0.062 (2)	0.092 (2)	0.0057 (18)	0.0133 (19)	−0.0208 (18)
C15	0.0688 (18)	0.072 (2)	0.103 (2)	−0.0173 (16)	0.0450 (17)	−0.0178 (18)
C16	0.0578 (18)	0.121 (4)	0.092 (2)	0.005 (2)	0.0159 (17)	−0.015 (2)
N1	0.0526 (12)	0.0489 (13)	0.0633 (12)	−0.0084 (10)	0.0172 (10)	−0.0106 (10)
O1	0.0615 (10)	0.0442 (11)	0.0550 (9)	−0.0092 (9)	−0.0007 (7)	0.0051 (8)
O2	0.0479 (9)	0.0705 (13)	0.0595 (9)	0.0014 (9)	0.0112 (7)	0.0008 (9)
O3	0.0887 (14)	0.0451 (10)	0.0451 (9)	0.0067 (10)	0.0129 (9)	0.0025 (8)
O4	0.0787 (14)	0.0814 (16)	0.0738 (13)	0.0186 (12)	0.0155 (11)	−0.0179 (11)
P1	0.0502 (3)	0.0422 (3)	0.0472 (3)	0.0003 (3)	0.0087 (2)	0.0005 (3)

Geometric parameters (Å, º) top

C1—C6	1.379 (4)	C11—C12	1.396 (5)
C1—C2	1.381 (4)	C11—H11	0.93
C1—O1	1.404 (3)	C12—H12	0.93
C2—C3	1.387 (4)	C13—N1	1.467 (3)
C2—H2	0.93	C13—C14	1.482 (4)
C3—C4	1.355 (5)	C13—H13A	0.97
C3—H3	0.93	C13—H13B	0.97
C4—C5	1.387 (5)	C14—O4	1.421 (4)
C4—H4	0.93	C14—H14A	0.97
C5—C6	1.381 (4)	C14—H14B	0.97
C5—H5	0.93	C15—N1	1.467 (3)
C6—H6	0.93	C15—C16	1.473 (5)
C7—C8	1.367 (4)	C15—H15A	0.97
C7—C12	1.372 (4)	C15—H15B	0.97
C7—O3	1.405 (3)	C16—O4	1.404 (5)
C8—C9	1.388 (5)	C16—H16A	0.97
C8—H8	0.93	C16—H16B	0.97
C9—C10	1.359 (6)	N1—P1	1.617 (2)
C9—H9	0.93	O1—P1	1.5922 (17)
C10—C11	1.354 (5)	O2—P1	1.4562 (18)
C10—H10	0.93	O3—P1	1.585 (2)

C6—C1—C2	121.7 (2)	N1—C13—C14	109.5 (2)
C6—C1—O1	118.3 (2)	N1—C13—H13A	109.8
C2—C1—O1	119.9 (2)	C14—C13—H13A	109.8
C1—C2—C3	118.1 (3)	N1—C13—H13B	109.8
C1—C2—H2	120.9	C14—C13—H13B	109.8
C3—C2—H2	120.9	H13A—C13—H13B	108.2
C4—C3—C2	121.3 (3)	O4—C14—C13	112.1 (3)
C4—C3—H3	119.4	O4—C14—H14A	109.2
C2—C3—H3	119.4	C13—C14—H14A	109.2
C3—C4—C5	119.9 (3)	O4—C14—H14B	109.2
C3—C4—H4	120	C13—C14—H14B	109.2
C5—C4—H4	120	H14A—C14—H14B	107.9
C6—C5—C4	120.3 (3)	N1—C15—C16	110.6 (3)
C6—C5—H5	119.9	N1—C15—H15A	109.5
C4—C5—H5	119.9	C16—C15—H15A	109.5
C1—C6—C5	118.6 (3)	N1—C15—H15B	109.5
C1—C6—H6	120.7	C16—C15—H15B	109.5
C5—C6—H6	120.7	H15A—C15—H15B	108.1
C8—C7—C12	121.2 (3)	O4—C16—C15	113.3 (3)
C8—C7—O3	119.2 (2)	O4—C16—H16A	108.9
C12—C7—O3	119.5 (3)	C15—C16—H16A	108.9
C7—C8—C9	118.9 (3)	O4—C16—H16B	108.9
C7—C8—H8	120.5	C15—C16—H16B	108.9
C9—C8—H8	120.5	H16A—C16—H16B	107.7
C10—C9—C8	120.6 (4)	C15—N1—C13	112.7 (2)
C10—C9—H9	119.7	C15—N1—P1	120.96 (19)
C8—C9—H9	119.7	C13—N1—P1	122.30 (17)
C11—C10—C9	120.1 (4)	C1—O1—P1	121.74 (15)
C11—C10—H10	119.9	C7—O3—P1	123.87 (14)
C9—C10—H10	119.9	C16—O4—C14	110.6 (2)
C10—C11—C12	120.7 (3)	O2—P1—O3	116.52 (11)
C10—C11—H11	119.6	O2—P1—O1	115.12 (9)
C12—C11—H11	119.6	O3—P1—O1	98.82 (10)
C7—C12—C11	118.4 (3)	O2—P1—N1	114.50 (11)
C7—C12—H12	120.8	O3—P1—N1	103.13 (11)
C11—C12—H12	120.8	O1—P1—N1	106.92 (11)

C6—C1—C2—C3	0.0 (4)	C14—C13—N1—C15	−52.0 (4)
O1—C1—C2—C3	175.8 (2)	C14—C13—N1—P1	150.5 (2)
C1—C2—C3—C4	−0.4 (5)	C6—C1—O1—P1	−112.4 (2)
C2—C3—C4—C5	−0.1 (5)	C2—C1—O1—P1	71.6 (3)
C3—C4—C5—C6	1.1 (5)	C8—C7—O3—P1	92.8 (3)
C2—C1—C6—C5	1.0 (4)	C12—C7—O3—P1	−90.7 (3)
O1—C1—C6—C5	−175.0 (3)	C15—C16—O4—C14	57.4 (4)
C4—C5—C6—C1	−1.5 (5)	C13—C14—O4—C16	−59.0 (4)
C12—C7—C8—C9	−1.3 (4)	C7—O3—P1—O2	−61.8 (2)
O3—C7—C8—C9	175.2 (2)	C7—O3—P1—O1	62.1 (2)
C7—C8—C9—C10	0.6 (5)	C7—O3—P1—N1	171.9 (2)
C8—C9—C10—C11	0.1 (5)	C1—O1—P1—O2	−50.3 (2)
C9—C10—C11—C12	−0.3 (5)	C1—O1—P1—O3	−175.21 (18)
C8—C7—C12—C11	1.1 (4)	C1—O1—P1—N1	78.08 (19)
O3—C7—C12—C11	−175.3 (2)	C15—N1—P1—O2	−169.9 (2)
C10—C11—C12—C7	−0.3 (4)	C13—N1—P1—O2	−14.2 (3)
N1—C13—C14—O4	56.1 (3)	C15—N1—P1—O3	−42.3 (3)
N1—C15—C16—O4	−53.1 (4)	C13—N1—P1—O3	113.4 (2)
C16—C15—N1—C13	50.4 (4)	C15—N1—P1—O1	61.4 (3)
C16—C15—N1—P1	−151.8 (2)	C13—N1—P1—O1	−143.0 (2)

(IV) top

Crystal data top

C₁₈H₁₅BrNO₃P	Z = 2
M_r = 404.19	F(000) = 408
Triclinic, P1	D_x = 1.483 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.1842 (2) Å	Cell parameters from 600 reflections
b = 10.2741 (2) Å	θ = 1–14°
c = 10.7121 (3) Å	µ = 2.37 mm⁻¹
α = 108.3036 (8)°	T = 293 K
β = 94.3109 (10)°	Prism, colourless
γ = 118.0843 (9)°	0.43 × 0.35 × 0.29 mm
V = 904.95 (4) Å³

Data collection top

KappaCCD diffractometer	4019 independent reflections
Radiation source: Enraf Nonius FR590	3259 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 3.8°
CCD rotation images, thick slices scans	h = −12→12
Absorption correction: multi-scan SADABS (Sheldrick, 2004)	k = −11→13
T_min = 0.428, T_max = 0.546	l = −13→13
11476 measured reflections

Refinement top

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0377P)² + 0.7366P] where P = (F_o² + 2F_c²)/3
4019 reflections	(Δ/σ)_max < 0.001
221 parameters	Δρ_max = 0.75 e Å⁻³
1 restraint	Δρ_min = −0.90 e Å⁻³

Special details top

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 > 2σ(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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	1.1855 (3)	0.7708 (3)	0.7538 (3)	0.0413 (6)
C2	1.1072 (4)	0.6164 (4)	0.7455 (4)	0.0661 (9)
H2	1.0011	0.551	0.7068	0.079*
C3	1.1886 (5)	0.5588 (5)	0.7956 (5)	0.0779 (12)
H3	1.1372	0.4543	0.7913	0.093*
C4	1.3449 (5)	0.6561 (5)	0.8516 (4)	0.0695 (10)
H4	1.3991	0.6175	0.886	0.083*
C5	1.4220 (4)	0.8095 (5)	0.8576 (4)	0.0695 (10)
H5	1.5283	0.8744	0.8951	0.083*
C6	1.3416 (4)	0.8688 (4)	0.8075 (3)	0.0565 (8)
H6	1.3931	0.9727	0.8106	0.068*
C7	0.8986 (3)	1.0471 (3)	0.6995 (3)	0.0394 (6)
C8	0.8648 (4)	1.0803 (4)	0.5919 (3)	0.0523 (7)
H8	0.8919	1.0468	0.5121	0.063*
C9	0.7902 (5)	1.1637 (5)	0.6026 (4)	0.0727 (11)
H9	0.7665	1.1863	0.5295	0.087*
C10	0.7506 (5)	1.2137 (5)	0.7194 (4)	0.0782 (12)
H10	0.7012	1.2712	0.7262	0.094*
C11	0.7836 (6)	1.1790 (6)	0.8259 (4)	0.0812 (13)
H11	0.7557	1.2123	0.9053	0.097*
C12	0.8580 (5)	1.0951 (5)	0.8176 (4)	0.0671 (10)
H12	0.8803	1.0714	0.8905	0.081*
C13	0.7601 (3)	0.6365 (3)	0.7361 (3)	0.0371 (5)
C14	0.7427 (3)	0.5713 (4)	0.5969 (3)	0.0478 (7)
H14	0.8159	0.6283	0.5577	0.057*
C15	0.6151 (4)	0.4201 (4)	0.5164 (3)	0.0565 (8)
H15	0.6039	0.3766	0.4232	0.068*
C16	0.5052 (4)	0.3336 (4)	0.5718 (3)	0.0541 (8)
H16	0.4205	0.2323	0.5174	0.065*
C17	0.5239 (3)	0.4012 (3)	0.7105 (3)	0.0440 (6)
C18	0.6495 (3)	0.5509 (3)	0.7936 (3)	0.0389 (6)
H18	0.66	0.5938	0.8868	0.047*
N1	0.8881 (2)	0.7876 (3)	0.8259 (2)	0.0389 (5)
O1	1.1424 (2)	1.0553 (2)	0.91797 (18)	0.0415 (4)
O2	1.1029 (2)	0.8281 (2)	0.69854 (18)	0.0398 (4)
O3	0.9737 (2)	0.9605 (2)	0.67965 (19)	0.0443 (4)
P1	1.03410 (7)	0.91819 (7)	0.79212 (7)	0.03352 (16)
Br1	0.37725 (4)	0.28278 (4)	0.79178 (4)	0.06523 (15)
H1	0.882 (4)	0.829 (4)	0.9082 (13)	0.054 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0490 (15)	0.0445 (14)	0.0415 (14)	0.0317 (13)	0.0191 (12)	0.0168 (12)
C2	0.0559 (19)	0.0548 (19)	0.104 (3)	0.0343 (17)	0.0261 (19)	0.041 (2)
C3	0.080 (3)	0.069 (2)	0.120 (3)	0.052 (2)	0.038 (3)	0.055 (2)
C4	0.093 (3)	0.087 (3)	0.064 (2)	0.072 (3)	0.026 (2)	0.029 (2)
C5	0.063 (2)	0.076 (3)	0.062 (2)	0.046 (2)	0.0002 (17)	0.0056 (18)
C6	0.0524 (18)	0.0468 (17)	0.0611 (19)	0.0270 (15)	0.0094 (15)	0.0100 (14)
C7	0.0445 (14)	0.0401 (14)	0.0426 (14)	0.0260 (12)	0.0173 (11)	0.0193 (11)
C8	0.0665 (19)	0.0649 (19)	0.0467 (16)	0.0441 (17)	0.0242 (14)	0.0293 (15)
C9	0.098 (3)	0.096 (3)	0.070 (2)	0.072 (3)	0.033 (2)	0.050 (2)
C10	0.101 (3)	0.102 (3)	0.089 (3)	0.084 (3)	0.042 (2)	0.051 (2)
C11	0.118 (3)	0.119 (3)	0.070 (2)	0.099 (3)	0.052 (2)	0.047 (2)
C12	0.098 (3)	0.101 (3)	0.0548 (19)	0.080 (3)	0.0409 (19)	0.0431 (19)
C13	0.0342 (13)	0.0342 (12)	0.0410 (14)	0.0177 (11)	0.0110 (11)	0.0129 (11)
C14	0.0469 (16)	0.0484 (16)	0.0402 (15)	0.0203 (13)	0.0123 (12)	0.0156 (13)
C15	0.0598 (19)	0.0504 (17)	0.0392 (15)	0.0216 (15)	0.0042 (14)	0.0078 (13)
C16	0.0461 (16)	0.0383 (15)	0.0587 (19)	0.0159 (13)	0.0002 (14)	0.0095 (14)
C17	0.0370 (14)	0.0340 (13)	0.0624 (18)	0.0183 (11)	0.0154 (13)	0.0206 (13)
C18	0.0380 (13)	0.0356 (13)	0.0446 (14)	0.0193 (11)	0.0154 (11)	0.0166 (11)
N1	0.0385 (12)	0.0345 (11)	0.0334 (11)	0.0122 (9)	0.0148 (9)	0.0112 (9)
O1	0.0403 (10)	0.0344 (9)	0.0417 (10)	0.0139 (8)	0.0168 (8)	0.0131 (8)
O2	0.0459 (10)	0.0438 (10)	0.0400 (10)	0.0288 (9)	0.0195 (8)	0.0183 (8)
O3	0.0603 (12)	0.0545 (11)	0.0421 (10)	0.0409 (10)	0.0266 (9)	0.0268 (9)
P1	0.0364 (3)	0.0322 (3)	0.0355 (3)	0.0181 (3)	0.0160 (3)	0.0158 (3)
Br1	0.0520 (2)	0.04161 (19)	0.0902 (3)	0.01322 (15)	0.02915 (18)	0.02790 (17)

Geometric parameters (Å, º) top

C1—C6	1.366 (4)	C11—C12	1.378 (5)
C1—C2	1.368 (4)	C11—H11	0.93
C1—O2	1.419 (3)	C12—H12	0.93
C2—C3	1.385 (5)	C13—C14	1.388 (4)
C2—H2	0.93	C13—C18	1.390 (4)
C3—C4	1.369 (6)	C13—N1	1.415 (3)
C3—H3	0.93	C14—C15	1.391 (4)
C4—C5	1.367 (6)	C14—H14	0.93
C4—H4	0.93	C15—C16	1.374 (5)
C5—C6	1.392 (5)	C15—H15	0.93
C5—H5	0.93	C16—C17	1.382 (4)
C6—H6	0.93	C16—H16	0.93
C7—C8	1.364 (4)	C17—C18	1.382 (4)
C7—C12	1.376 (4)	C17—Br1	1.903 (3)
C7—O3	1.404 (3)	C18—H18	0.93
C8—C9	1.374 (5)	N1—P1	1.627 (2)
C8—H8	0.93	N1—H1	0.874 (4)
C9—C10	1.363 (5)	O1—P1	1.4626 (19)
C9—H9	0.93	O2—P1	1.5769 (18)
C10—C11	1.362 (5)	O3—P1	1.5772 (19)
C10—H10	0.93

C6—C1—C2	122.0 (3)	C7—C12—C11	118.7 (3)
C6—C1—O2	119.0 (3)	C7—C12—H12	120.6
C2—C1—O2	118.9 (3)	C11—C12—H12	120.6
C1—C2—C3	118.9 (3)	C14—C13—C18	119.8 (3)
C1—C2—H2	120.5	C14—C13—N1	123.2 (2)
C3—C2—H2	120.5	C18—C13—N1	117.0 (2)
C4—C3—C2	119.9 (4)	C13—C14—C15	119.5 (3)
C4—C3—H3	120.1	C13—C14—H14	120.2
C2—C3—H3	120.1	C15—C14—H14	120.2
C5—C4—C3	120.6 (3)	C16—C15—C14	121.4 (3)
C5—C4—H4	119.7	C16—C15—H15	119.3
C3—C4—H4	119.7	C14—C15—H15	119.3
C4—C5—C6	120.1 (4)	C15—C16—C17	118.2 (3)
C4—C5—H5	120	C15—C16—H16	120.9
C6—C5—H5	120	C17—C16—H16	120.9
C1—C6—C5	118.5 (3)	C18—C17—C16	121.9 (3)
C1—C6—H6	120.8	C18—C17—Br1	118.5 (2)
C5—C6—H6	120.8	C16—C17—Br1	119.5 (2)
C8—C7—C12	120.9 (3)	C17—C18—C13	119.1 (3)
C8—C7—O3	115.6 (2)	C17—C18—H18	120.4
C12—C7—O3	123.5 (2)	C13—C18—H18	120.4
C7—C8—C9	119.2 (3)	C13—N1—P1	129.42 (18)
C7—C8—H8	120.4	C13—N1—H1	117 (2)
C9—C8—H8	120.4	P1—N1—H1	112 (2)
C10—C9—C8	120.7 (3)	C1—O2—P1	120.04 (16)
C10—C9—H9	119.6	C7—O3—P1	124.83 (16)
C8—C9—H9	119.6	O1—P1—O2	116.23 (11)
C11—C10—C9	119.7 (3)	O1—P1—O3	115.60 (11)
C11—C10—H10	120.2	O2—P1—O3	95.39 (10)
C9—C10—H10	120.2	O1—P1—N1	110.43 (11)
C10—C11—C12	120.8 (3)	O2—P1—N1	108.56 (11)
C10—C11—H11	119.6	O3—P1—N1	109.64 (12)
C12—C11—H11	119.6

C6—C1—C2—C3	1.3 (5)	C15—C16—C17—Br1	−178.3 (2)
O2—C1—C2—C3	178.0 (3)	C16—C17—C18—C13	0.4 (4)
C1—C2—C3—C4	−0.3 (6)	Br1—C17—C18—C13	178.0 (2)
C2—C3—C4—C5	−0.6 (6)	C14—C13—C18—C17	0.2 (4)
C3—C4—C5—C6	0.6 (6)	N1—C13—C18—C17	−178.7 (2)
C2—C1—C6—C5	−1.3 (5)	C14—C13—N1—P1	2.6 (4)
O2—C1—C6—C5	−178.0 (3)	C18—C13—N1—P1	−178.6 (2)
C4—C5—C6—C1	0.4 (5)	C6—C1—O2—P1	−90.6 (3)
C12—C7—C8—C9	0.5 (5)	C2—C1—O2—P1	92.6 (3)
O3—C7—C8—C9	179.5 (3)	C8—C7—O3—P1	175.7 (2)
C7—C8—C9—C10	0.2 (6)	C12—C7—O3—P1	−5.2 (4)
C8—C9—C10—C11	−0.8 (7)	C1—O2—P1—O1	53.6 (2)
C9—C10—C11—C12	0.6 (8)	C1—O2—P1—O3	175.64 (19)
C8—C7—C12—C11	−0.6 (6)	C1—O2—P1—N1	−71.5 (2)
O3—C7—C12—C11	−179.6 (4)	C7—O3—P1—O1	−56.5 (2)
C10—C11—C12—C7	0.1 (7)	C7—O3—P1—O2	−179.0 (2)
C18—C13—C14—C15	−0.4 (4)	C7—O3—P1—N1	69.0 (2)
N1—C13—C14—C15	178.4 (3)	C13—N1—P1—O1	−177.8 (2)
C13—C14—C15—C16	0.1 (5)	C13—N1—P1—O2	−49.3 (3)
C14—C15—C16—C17	0.4 (5)	C13—N1—P1—O3	53.7 (3)
C15—C16—C17—C18	−0.7 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.87 (1)	1.97 (1)	2.837 (3)	170 (3)

Symmetry code: (i) −x+2, −y+2, −z+2.

(V) top

Crystal data top

C₃₂H₄₀N₄O₃P₂	F(000) = 1256
M_r = 590.62	D_x = 1.293 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -C 2yc	Cell parameters from 3174 reflections
a = 19.050 (3) Å	θ = 32.9–68.5°
b = 8.5308 (12) Å	µ = 1.62 mm⁻¹
c = 18.821 (3) Å	T = 100 K
β = 97.341 (6)°	Block, colorless
V = 3033.6 (8) Å³	0.20 × 0.10 × 0.10 mm
Z = 4

Data collection top

Bruker APEX-II CCD diffractometer	2662 independent reflections
Radiation source: Cu rotating anode	2640 reflections with I > 2σ(I)
Doubly curved mirrors monochromator	R_int = 0.050
φ and ω scans	θ_max = 68.2°, θ_min = 5.7°
Absorption correction: multi-scan SADABS (Sheldrick, 2004)	h = −21→15
T_min = 0.738, T_max = 0.855	k = −10→10
12338 measured reflections	l = −22→22

Refinement top

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0337P)² + 3.5908P] where P = (F_o² + 2F_c²)/3
2662 reflections	(Δ/σ)_max < 0.001
188 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
P1	0.011654 (17)	0.71027 (4)	0.176053 (16)	0.01157 (13)
O1	−0.04695 (5)	0.60378 (11)	0.15054 (5)	0.0157 (2)
O2	0.0000	0.79683 (14)	0.2500	0.0134 (3)
N1	0.08733 (6)	0.61642 (13)	0.18719 (6)	0.0142 (3)
N2	0.02439 (6)	0.86483 (13)	0.12811 (6)	0.0149 (3)
C1	0.08950 (7)	0.44947 (15)	0.20642 (7)	0.0157 (3)
H1B	0.0404	0.4097	0.2043	0.019*
H1C	0.1125	0.4379	0.2563	0.019*
C2	0.12904 (7)	0.35087 (15)	0.15763 (7)	0.0149 (3)
C3	0.11774 (7)	0.37084 (16)	0.08350 (7)	0.0177 (3)
H3A	0.0877	0.4527	0.0634	0.021*
C4	0.15001 (8)	0.27189 (17)	0.03880 (8)	0.0217 (3)
H4A	0.1421	0.2866	−0.0116	0.026*
C5	0.19373 (8)	0.15171 (17)	0.06763 (8)	0.0235 (3)
H5A	0.2154	0.0835	0.0370	0.028*
C6	0.20569 (8)	0.13143 (17)	0.14134 (8)	0.0228 (3)
H6A	0.2358	0.0495	0.1612	0.027*
C7	0.17354 (7)	0.23109 (16)	0.18622 (8)	0.0183 (3)
H7A	0.1821	0.2171	0.2367	0.022*
C8	0.15271 (7)	0.70078 (17)	0.21266 (8)	0.0213 (3)
H8A	0.1931	0.6459	0.1968	0.032*
H8B	0.1586	0.7055	0.2651	0.032*
H8C	0.1501	0.8074	0.1931	0.032*
C9	0.00910 (7)	1.02782 (15)	0.14534 (7)	0.0154 (3)
H9A	0.0402	1.0968	0.1209	0.018*
H9B	0.0218	1.0430	0.1975	0.018*
C10	−0.06688 (7)	1.08148 (16)	0.12518 (6)	0.0144 (3)
C11	−0.07994 (8)	1.23960 (16)	0.10948 (7)	0.0174 (3)
H11A	−0.0413	1.3102	0.1102	0.021*
C12	−0.14850 (8)	1.29522 (17)	0.09286 (8)	0.0211 (3)
H12A	−0.1565	1.4032	0.0823	0.025*
C13	−0.20529 (8)	1.19326 (18)	0.09159 (8)	0.0211 (3)
H13A	−0.2523	1.2307	0.0798	0.025*
C14	−0.19302 (8)	1.03562 (17)	0.10775 (7)	0.0206 (3)
H14A	−0.2318	0.9656	0.1075	0.025*
C15	−0.12434 (7)	0.98018 (16)	0.12429 (7)	0.0175 (3)
H15A	−0.1165	0.8723	0.1351	0.021*
C16	0.03594 (8)	0.83547 (17)	0.05376 (7)	0.0196 (3)
H16A	0.0740	0.9034	0.0413	0.029*
H16B	−0.0077	0.8580	0.0218	0.029*
H16C	0.0492	0.7255	0.0484	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0131 (2)	0.00983 (19)	0.01208 (19)	0.00006 (12)	0.00281 (13)	0.00041 (11)
O1	0.0161 (5)	0.0134 (5)	0.0177 (5)	−0.0012 (4)	0.0021 (4)	−0.0003 (4)
O2	0.0161 (7)	0.0101 (6)	0.0147 (6)	0.000	0.0044 (5)	0.000
N1	0.0143 (6)	0.0118 (5)	0.0168 (5)	−0.0002 (4)	0.0033 (4)	−0.0004 (4)
N2	0.0197 (6)	0.0116 (6)	0.0139 (5)	0.0008 (4)	0.0043 (4)	0.0013 (4)
C1	0.0174 (7)	0.0133 (7)	0.0170 (6)	0.0026 (5)	0.0043 (5)	0.0018 (5)
C2	0.0118 (6)	0.0127 (6)	0.0208 (7)	−0.0028 (5)	0.0041 (5)	−0.0017 (5)
C3	0.0169 (7)	0.0149 (7)	0.0216 (7)	−0.0030 (5)	0.0037 (5)	−0.0005 (5)
C4	0.0233 (8)	0.0218 (7)	0.0214 (7)	−0.0080 (6)	0.0083 (6)	−0.0054 (6)
C5	0.0194 (8)	0.0204 (7)	0.0326 (8)	−0.0043 (6)	0.0103 (6)	−0.0123 (6)
C6	0.0157 (7)	0.0171 (7)	0.0350 (8)	0.0019 (5)	0.0010 (6)	−0.0053 (6)
C7	0.0156 (7)	0.0164 (7)	0.0224 (7)	−0.0004 (5)	0.0007 (5)	−0.0021 (5)
C8	0.0147 (7)	0.0207 (7)	0.0285 (8)	−0.0003 (5)	0.0027 (6)	−0.0036 (6)
C9	0.0191 (7)	0.0110 (6)	0.0161 (6)	−0.0026 (5)	0.0027 (5)	0.0015 (5)
C10	0.0188 (7)	0.0140 (6)	0.0106 (6)	−0.0011 (5)	0.0034 (5)	−0.0016 (5)
C11	0.0224 (7)	0.0140 (6)	0.0165 (6)	−0.0018 (6)	0.0047 (5)	−0.0008 (5)
C12	0.0283 (8)	0.0159 (7)	0.0197 (7)	0.0056 (6)	0.0054 (6)	0.0021 (5)
C13	0.0191 (7)	0.0254 (8)	0.0191 (7)	0.0053 (6)	0.0034 (5)	−0.0011 (6)
C14	0.0184 (7)	0.0222 (7)	0.0216 (7)	−0.0030 (6)	0.0038 (5)	−0.0016 (6)
C15	0.0219 (7)	0.0136 (7)	0.0174 (6)	−0.0012 (5)	0.0034 (5)	0.0001 (5)
C16	0.0264 (8)	0.0177 (7)	0.0157 (7)	0.0020 (6)	0.0061 (5)	0.0025 (5)

Geometric parameters (Å, º) top

P1—O1	1.4715 (10)	C7—H7A	0.9500
P1—O2	1.6157 (6)	C8—H8A	0.9800
P1—N2	1.6333 (11)	C8—H8B	0.9800
P1—N1	1.6389 (11)	C8—H8C	0.9800
O2—P1ⁱ	1.6158 (6)	C9—C10	1.5194 (19)
N1—C8	1.4650 (17)	C9—H9A	0.9900
N1—C1	1.4688 (17)	C9—H9B	0.9900
N2—C9	1.4655 (17)	C10—C15	1.3931 (19)
N2—C16	1.4656 (17)	C10—C11	1.3964 (19)
C1—C2	1.5149 (18)	C11—C12	1.387 (2)
C1—H1B	0.9900	C11—H11A	0.9500
C1—H1C	0.9900	C12—C13	1.386 (2)
C2—C7	1.3914 (19)	C12—H12A	0.9500
C2—C3	1.3947 (19)	C13—C14	1.392 (2)
C3—C4	1.389 (2)	C13—H13A	0.9500
C3—H3A	0.9500	C14—C15	1.388 (2)
C4—C5	1.387 (2)	C14—H14A	0.9500
C4—H4A	0.9500	C15—H15A	0.9500
C5—C6	1.388 (2)	C16—H16A	0.9800
C5—H5A	0.9500	C16—H16B	0.9800
C6—C7	1.394 (2)	C16—H16C	0.9800
C6—H6A	0.9500

O1—P1—O2	112.41 (5)	N1—C8—H8A	109.5
O1—P1—N2	118.57 (6)	N1—C8—H8B	109.5
O2—P1—N2	98.83 (6)	H8A—C8—H8B	109.5
O1—P1—N1	111.01 (6)	N1—C8—H8C	109.5
O2—P1—N1	109.18 (4)	H8A—C8—H8C	109.5
N2—P1—N1	105.94 (6)	H8B—C8—H8C	109.5
P1—O2—P1ⁱ	125.61 (8)	N2—C9—C10	116.14 (11)
C8—N1—C1	113.57 (11)	N2—C9—H9A	108.3
C8—N1—P1	119.94 (9)	C10—C9—H9A	108.3
C1—N1—P1	120.11 (9)	N2—C9—H9B	108.3
C9—N2—C16	115.58 (10)	C10—C9—H9B	108.3
C9—N2—P1	126.58 (9)	H9A—C9—H9B	107.4
C16—N2—P1	116.14 (9)	C15—C10—C11	118.57 (13)
N1—C1—C2	112.92 (11)	C15—C10—C9	122.56 (12)
N1—C1—H1B	109.0	C11—C10—C9	118.83 (12)
C2—C1—H1B	109.0	C12—C11—C10	121.01 (13)
N1—C1—H1C	109.0	C12—C11—H11A	119.5
C2—C1—H1C	109.0	C10—C11—H11A	119.5
H1B—C1—H1C	107.8	C13—C12—C11	119.97 (13)
C7—C2—C3	119.02 (13)	C13—C12—H12A	120.0
C7—C2—C1	119.93 (12)	C11—C12—H12A	120.0
C3—C2—C1	120.89 (12)	C12—C13—C14	119.58 (14)
C4—C3—C2	120.52 (13)	C12—C13—H13A	120.2
C4—C3—H3A	119.7	C14—C13—H13A	120.2
C2—C3—H3A	119.7	C15—C14—C13	120.35 (14)
C5—C4—C3	120.15 (14)	C15—C14—H14A	119.8
C5—C4—H4A	119.9	C13—C14—H14A	119.8
C3—C4—H4A	119.9	C14—C15—C10	120.51 (13)
C4—C5—C6	119.79 (13)	C14—C15—H15A	119.7
C4—C5—H5A	120.1	C10—C15—H15A	119.7
C6—C5—H5A	120.1	N2—C16—H16A	109.5
C5—C6—C7	120.07 (14)	N2—C16—H16B	109.5
C5—C6—H6A	120.0	H16A—C16—H16B	109.5
C7—C6—H6A	120.0	N2—C16—H16C	109.5
C2—C7—C6	120.44 (14)	H16A—C16—H16C	109.5
C2—C7—H7A	119.8	H16B—C16—H16C	109.5
C6—C7—H7A	119.8

O1—P1—O2—P1ⁱ	57.39 (4)	C1—C2—C3—C4	−174.97 (12)
N2—P1—O2—P1ⁱ	−176.63 (4)	C2—C3—C4—C5	0.2 (2)
N1—P1—O2—P1ⁱ	−66.25 (5)	C3—C4—C5—C6	−0.6 (2)
O1—P1—N1—C8	−179.80 (9)	C4—C5—C6—C7	0.3 (2)
O2—P1—N1—C8	−55.33 (11)	C3—C2—C7—C6	−0.7 (2)
N2—P1—N1—C8	50.24 (11)	C1—C2—C7—C6	174.75 (12)
O1—P1—N1—C1	−29.65 (11)	C5—C6—C7—C2	0.3 (2)
O2—P1—N1—C1	94.82 (10)	C16—N2—C9—C10	81.28 (14)
N2—P1—N1—C1	−159.61 (9)	P1—N2—C9—C10	−83.20 (14)
O1—P1—N2—C9	107.25 (11)	N2—C9—C10—C15	30.75 (17)
O2—P1—N2—C9	−14.35 (11)	N2—C9—C10—C11	−151.68 (12)
N1—P1—N2—C9	−127.31 (11)	C15—C10—C11—C12	−0.41 (19)
O1—P1—N2—C16	−57.16 (12)	C9—C10—C11—C12	−178.07 (12)
O2—P1—N2—C16	−178.75 (9)	C10—C11—C12—C13	−0.1 (2)
N1—P1—N2—C16	68.29 (11)	C11—C12—C13—C14	0.6 (2)
C8—N1—C1—C2	−79.60 (14)	C12—C13—C14—C15	−0.7 (2)
P1—N1—C1—C2	128.47 (10)	C13—C14—C15—C10	0.2 (2)
N1—C1—C2—C7	139.80 (12)	C11—C10—C15—C14	0.33 (19)
N1—C1—C2—C3	−44.81 (17)	C9—C10—C15—C14	177.91 (12)
C7—C2—C3—C4	0.5 (2)

Symmetry code: (i) −x, y, −z+1/2.

(VI) top

Crystal data top

C₂₈H₃₂N₄O₃P₂	D_x = 1.313 Mg m⁻³
M_r = 534.52	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pccn	Cell parameters from 9950 reflections
a = 13.4363 (9) Å	θ = 2.8–27.2°
b = 20.3532 (13) Å	µ = 0.20 mm⁻¹
c = 9.8851 (6) Å	T = 90 K
V = 2703.3 (3) Å³	BLOCK, colourless
Z = 4	0.28 × 0.10 × 0.10 mm
F(000) = 1128

Data collection top

Bruker APEX-II CCD diffractometer	3021 independent reflections
Radiation source: fine-focus sealed tube	2613 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
φ and ω scans	θ_max = 27.2°, θ_min = 2.8°
Absorption correction: multi-scan SADABS (Sheldrick, 2004)	h = −17→17
T_min = 0.947, T_max = 0.981	k = −25→26
21713 measured reflections	l = −12→12

Refinement top

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0464P)² + 2.0756P] where P = (F_o² + 2F_c²)/3
3021 reflections	(Δ/σ)_max = 0.017
176 parameters	Δρ_max = 0.40 e Å⁻³
2 restraints	Δρ_min = −0.36 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
P1	0.66141 (3)	0.711940 (19)	0.54774 (4)	0.01271 (12)
O1	0.7500	0.7500	0.47179 (14)	0.0136 (3)
O2	0.62320 (8)	0.74693 (6)	0.66640 (10)	0.0189 (2)
N1	0.70297 (10)	0.63958 (7)	0.59323 (13)	0.0174 (3)
H1N	0.7206 (14)	0.6402 (9)	0.6772 (11)	0.021*
N2	0.58768 (9)	0.70329 (6)	0.41932 (12)	0.0138 (3)
H2N	0.6069 (13)	0.7211 (8)	0.3454 (12)	0.017*
C1	0.76183 (11)	0.60001 (7)	0.50390 (16)	0.0168 (3)
C2	0.86464 (12)	0.59971 (8)	0.51515 (18)	0.0220 (3)
H2A	0.8964	0.6253	0.5830	0.026*
C3	0.92079 (13)	0.56202 (8)	0.42709 (19)	0.0250 (4)
H3A	0.9912	0.5616	0.4364	0.030*
C4	0.87690 (13)	0.52478 (8)	0.32545 (17)	0.0219 (3)
C5	0.77378 (12)	0.52519 (8)	0.31648 (17)	0.0209 (3)
H5A	0.7420	0.4997	0.2486	0.025*
C6	0.71618 (12)	0.56224 (8)	0.40504 (17)	0.0196 (3)
H6A	0.6457	0.5617	0.3978	0.024*
C7	0.93964 (15)	0.48668 (9)	0.2267 (2)	0.0313 (4)
H7A	0.9122	0.4424	0.2160	0.047*
H7B	1.0080	0.4837	0.2609	0.047*
H7C	0.9396	0.5091	0.1390	0.047*
C8	0.48717 (11)	0.68338 (7)	0.42887 (15)	0.0144 (3)
C9	0.45075 (12)	0.64930 (8)	0.54057 (16)	0.0186 (3)
H9A	0.4939	0.6382	0.6131	0.022*
C10	0.35111 (12)	0.63166 (8)	0.54528 (17)	0.0217 (3)
H10A	0.3270	0.6084	0.6218	0.026*
C11	0.28565 (12)	0.64707 (8)	0.44133 (17)	0.0215 (3)
C12	0.32386 (12)	0.68041 (8)	0.32971 (17)	0.0205 (3)
H12A	0.2808	0.6911	0.2567	0.025*
C13	0.42303 (11)	0.69835 (7)	0.32283 (16)	0.0171 (3)
H13A	0.4474	0.7209	0.2455	0.021*
C14	0.17736 (13)	0.62836 (10)	0.44902 (19)	0.0302 (4)
H14A	0.1714	0.5804	0.4543	0.045*
H14B	0.1428	0.6442	0.3681	0.045*
H14C	0.1474	0.6482	0.5296	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.01118 (19)	0.0169 (2)	0.0101 (2)	−0.00020 (13)	0.00030 (13)	0.00116 (13)
O1	0.0128 (7)	0.0181 (7)	0.0099 (7)	−0.0022 (6)	0.000	0.000
O2	0.0173 (5)	0.0271 (6)	0.0124 (5)	0.0008 (4)	0.0013 (4)	−0.0021 (4)
N1	0.0167 (6)	0.0215 (7)	0.0141 (6)	0.0024 (5)	−0.0002 (5)	0.0044 (5)
N2	0.0118 (6)	0.0190 (6)	0.0105 (6)	−0.0024 (5)	0.0000 (5)	0.0027 (5)
C1	0.0162 (7)	0.0150 (7)	0.0192 (7)	0.0010 (5)	0.0005 (6)	0.0060 (6)
C2	0.0169 (8)	0.0193 (8)	0.0300 (9)	−0.0005 (6)	−0.0032 (7)	−0.0018 (7)
C3	0.0157 (8)	0.0198 (8)	0.0395 (10)	0.0007 (6)	0.0000 (7)	−0.0018 (7)
C4	0.0245 (8)	0.0137 (7)	0.0276 (9)	0.0015 (6)	0.0041 (7)	0.0039 (6)
C5	0.0253 (9)	0.0154 (7)	0.0221 (8)	−0.0019 (6)	−0.0027 (6)	0.0030 (6)
C6	0.0164 (7)	0.0179 (7)	0.0246 (8)	−0.0018 (6)	−0.0018 (6)	0.0051 (6)
C7	0.0343 (10)	0.0211 (8)	0.0386 (11)	0.0042 (7)	0.0078 (8)	−0.0032 (8)
C8	0.0121 (7)	0.0149 (7)	0.0161 (7)	−0.0006 (5)	0.0007 (5)	−0.0015 (5)
C9	0.0163 (7)	0.0228 (8)	0.0167 (7)	−0.0019 (6)	−0.0005 (6)	0.0027 (6)
C10	0.0198 (8)	0.0260 (8)	0.0194 (8)	−0.0046 (6)	0.0044 (6)	0.0042 (6)
C11	0.0143 (7)	0.0250 (8)	0.0253 (8)	−0.0032 (6)	0.0019 (6)	−0.0007 (7)
C12	0.0153 (7)	0.0241 (8)	0.0220 (8)	−0.0003 (6)	−0.0036 (6)	0.0001 (6)
C13	0.0166 (7)	0.0179 (7)	0.0169 (7)	−0.0011 (6)	−0.0005 (6)	0.0019 (6)
C14	0.0164 (8)	0.0436 (11)	0.0307 (10)	−0.0079 (7)	0.0009 (7)	0.0039 (8)

Geometric parameters (Å, º) top

P1—O2	1.4651 (11)	C6—H6A	0.9500
P1—O1	1.6064 (7)	C7—H7A	0.9800
P1—N2	1.6199 (13)	C7—H7B	0.9800
P1—N1	1.6380 (14)	C7—H7C	0.9800
O1—P1ⁱ	1.6064 (7)	C8—C13	1.391 (2)
N1—C1	1.433 (2)	C8—C9	1.393 (2)
N1—H1N	0.863 (9)	C9—C10	1.387 (2)
N2—C8	1.4132 (19)	C9—H9A	0.9500
N2—H2N	0.856 (9)	C10—C11	1.388 (2)
C1—C2	1.386 (2)	C10—H10A	0.9500
C1—C6	1.386 (2)	C11—C12	1.393 (2)
C2—C3	1.384 (2)	C11—C14	1.506 (2)
C2—H2A	0.9500	C12—C13	1.383 (2)
C3—C4	1.390 (2)	C12—H12A	0.9500
C3—H3A	0.9500	C13—H13A	0.9500
C4—C5	1.388 (2)	C14—H14A	0.9800
C4—C7	1.505 (2)	C14—H14B	0.9800
C5—C6	1.391 (2)	C14—H14C	0.9800
C5—H5A	0.9500

O2—P1—O1	113.54 (6)	C4—C7—H7A	109.5
O2—P1—N2	117.77 (7)	C4—C7—H7B	109.5
O1—P1—N2	98.00 (6)	H7A—C7—H7B	109.5
O2—P1—N1	109.68 (7)	C4—C7—H7C	109.5
O1—P1—N1	108.02 (5)	H7A—C7—H7C	109.5
N2—P1—N1	109.02 (7)	H7B—C7—H7C	109.5
P1ⁱ—O1—P1	124.27 (9)	C13—C8—C9	119.27 (14)
C1—N1—P1	121.62 (10)	C13—C8—N2	118.62 (13)
C1—N1—H1N	116.7 (13)	C9—C8—N2	122.11 (14)
P1—N1—H1N	110.2 (13)	C10—C9—C8	119.65 (14)
C8—N2—P1	124.28 (10)	C10—C9—H9A	120.2
C8—N2—H2N	117.8 (13)	C8—C9—H9A	120.2
P1—N2—H2N	116.0 (13)	C9—C10—C11	121.88 (15)
C2—C1—C6	119.68 (15)	C9—C10—H10A	119.1
C2—C1—N1	120.20 (15)	C11—C10—H10A	119.1
C6—C1—N1	120.11 (14)	C10—C11—C12	117.56 (14)
C3—C2—C1	119.69 (16)	C10—C11—C14	121.17 (15)
C3—C2—H2A	120.2	C12—C11—C14	121.27 (15)
C1—C2—H2A	120.2	C13—C12—C11	121.50 (15)
C2—C3—C4	121.71 (16)	C13—C12—H12A	119.3
C2—C3—H3A	119.1	C11—C12—H12A	119.3
C4—C3—H3A	119.1	C12—C13—C8	120.13 (14)
C5—C4—C3	117.80 (15)	C12—C13—H13A	119.9
C5—C4—C7	121.38 (16)	C8—C13—H13A	119.9
C3—C4—C7	120.80 (16)	C11—C14—H14A	109.5
C4—C5—C6	121.22 (15)	C11—C14—H14B	109.5
C4—C5—H5A	119.4	H14A—C14—H14B	109.5
C6—C5—H5A	119.4	C11—C14—H14C	109.5
C1—C6—C5	119.88 (15)	H14A—C14—H14C	109.5
C1—C6—H6A	120.1	H14B—C14—H14C	109.5
C5—C6—H6A	120.1

O2—P1—O1—P1ⁱ	40.76 (5)	C7—C4—C5—C6	−177.78 (15)
N2—P1—O1—P1ⁱ	165.82 (5)	C2—C1—C6—C5	−1.0 (2)
N1—P1—O1—P1ⁱ	−81.11 (5)	N1—C1—C6—C5	178.42 (14)
O2—P1—N1—C1	−167.66 (12)	C4—C5—C6—C1	0.5 (2)
O1—P1—N1—C1	−43.43 (14)	P1—N2—C8—C13	158.75 (12)
N2—P1—N1—C1	62.05 (14)	P1—N2—C8—C9	−21.4 (2)
O2—P1—N2—C8	−45.62 (14)	C13—C8—C9—C10	−0.9 (2)
O1—P1—N2—C8	−167.62 (11)	N2—C8—C9—C10	179.22 (15)
N1—P1—N2—C8	80.11 (13)	C8—C9—C10—C11	−0.1 (3)
P1—N1—C1—C2	97.96 (16)	C9—C10—C11—C12	0.9 (3)
P1—N1—C1—C6	−81.50 (17)	C9—C10—C11—C14	−179.13 (17)
C6—C1—C2—C3	0.4 (2)	C10—C11—C12—C13	−0.8 (2)
N1—C1—C2—C3	−179.09 (15)	C14—C11—C12—C13	179.27 (16)
C1—C2—C3—C4	0.9 (3)	C11—C12—C13—C8	−0.2 (2)
C2—C3—C4—C5	−1.5 (2)	C9—C8—C13—C12	1.0 (2)
C2—C3—C4—C7	177.10 (16)	N2—C8—C13—C12	−179.08 (14)
C3—C4—C5—C6	0.8 (2)

Symmetry code: (i) −x+3/2, −y+3/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O2ⁱⁱ	0.86 (1)	1.90 (1)	2.7395 (16)	168 (2)
C13—H13A···O2ⁱⁱ	0.95	2.57	3.2963 (19)	133

Symmetry code: (ii) x, −y+3/2, z−1/2.

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