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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 de and di 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).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052519213009445/so5063sup1.cif
Contains datablocks I, II, III, IV, V, VI, New_Global_Publ_Block

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052519213009445/so5063Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052519213009445/so5063IIsup3.hkl
Contains datablock atar17

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052519213009445/so5063IIIsup4.hkl
Contains datablock tm16

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052519213009445/so5063IVsup5.hkl
Contains datablock tm18

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052519213009445/so5063Vsup6.hkl
Contains datablock V

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052519213009445/so5063VIsup7.hkl
Contains datablock atar29

pdf

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
C15H24F2N3O2PZ = 4
Mr = 347.34F(000) = 736
Triclinic, P1Dx = 1.322 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.8932 (17) ÅCell parameters from 9914 reflections
b = 10.5022 (19) Åθ = 2.6–27.9°
c = 19.228 (4) ŵ = 0.19 mm1
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 tube6659 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
φ and ω scansθmax = 28.0°, θmin = 1.1°
Absorption correction: multi-scan
SADABS (Sheldrick, 2004)
h = 1113
Tmin = 0.928, Tmax = 0.946k = 1313
26911 measured reflectionsl = 2424
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0418P)2 + 0.9075P]
where P = (Fo2 + 2Fc2)/3
7845 reflections(Δ/σ)max < 0.001
429 parametersΔρmax = 0.39 e Å3
2 restraintsΔρmin = 0.39 e Å3
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
xyzUiso*/Ueq
C10.36725 (18)0.50983 (18)0.37040 (9)0.0222 (3)
C20.27153 (19)0.50361 (19)0.42932 (9)0.0269 (4)
H20.16410.55530.42790.032*
C30.3364 (2)0.42014 (19)0.49035 (9)0.0267 (4)
H30.27230.41400.53140.032*
C40.49335 (19)0.34488 (18)0.49317 (8)0.0235 (3)
H40.53750.28780.53540.028*
C50.58277 (17)0.35580 (17)0.43266 (8)0.0191 (3)
C60.52536 (17)0.43714 (17)0.36951 (8)0.0177 (3)
C70.62929 (16)0.43744 (17)0.30371 (8)0.0174 (3)
C80.92667 (17)0.52223 (18)0.27516 (9)0.0223 (3)
H8A1.03930.47330.26870.027*
H8B0.89270.45140.30250.027*
C90.8793 (2)0.6464 (2)0.31835 (9)0.0283 (4)
H9A0.91550.71560.29270.042*
H9B0.92380.60900.36420.042*
H9C0.76800.69460.32590.042*
C100.96724 (18)0.58297 (19)0.14447 (9)0.0243 (3)
H10A0.91490.60710.10050.029*
H10B1.05930.49000.14130.029*
C111.01599 (19)0.6988 (2)0.14853 (9)0.0282 (4)
H11A0.92550.79020.15430.042*
H11B1.07630.71020.10480.042*
H11C1.07760.67070.18910.042*
C120.81481 (17)0.36645 (17)0.12556 (8)0.0205 (3)
H12A0.77400.29550.14340.025*
H12B0.89890.34560.15470.025*
C130.8768 (2)0.3491 (2)0.04897 (9)0.0313 (4)
H13A0.79590.36160.02070.047*
H13B0.96140.25270.04640.047*
H13C0.91330.42200.03040.047*
C140.55368 (18)0.55841 (18)0.09716 (9)0.0231 (3)
H14A0.58190.55120.04590.028*
H14B0.48570.66090.10250.028*
C150.4669 (2)0.4705 (2)0.12475 (12)0.0415 (5)
H15A0.53120.36970.11720.062*
H15B0.37460.50840.09940.062*
H15C0.43880.47660.17550.062*
C160.2397 (2)0.9663 (2)0.09606 (9)0.0281 (4)
C170.2472 (2)0.9474 (2)0.02632 (10)0.0377 (5)
H170.22600.87480.01410.045*
C180.2864 (2)1.0363 (2)0.02542 (10)0.0374 (5)
H180.29281.02450.07380.045*
C190.3162 (2)1.1420 (2)0.00787 (9)0.0327 (4)
H190.34401.20270.04350.039*
C200.30468 (18)1.15756 (19)0.06270 (9)0.0249 (3)
C210.26684 (17)1.07181 (17)0.11688 (8)0.0188 (3)
C220.25296 (16)1.09563 (17)0.19325 (8)0.0178 (3)
C230.12535 (18)0.94247 (19)0.38934 (9)0.0241 (3)
H23A0.04940.98070.42930.029*
H23B0.19850.84290.40610.029*
C240.0443 (2)0.9380 (2)0.32910 (11)0.0330 (4)
H24A0.02551.03650.31090.050*
H24B0.01340.88230.34660.050*
H24C0.11970.89240.29100.050*
C250.11302 (17)1.18718 (17)0.37192 (8)0.0200 (3)
H25A0.01571.21620.35130.024*
H25B0.16541.24110.34240.024*
C260.07895 (18)1.22901 (19)0.44651 (9)0.0251 (3)
H26A0.03051.17340.47660.038*
H26B0.01021.33220.44520.038*
H26C0.17421.20840.46590.038*
C270.50288 (18)1.14751 (18)0.26613 (8)0.0212 (3)
H27A0.51661.22410.28330.025*
H27B0.42081.19510.23310.025*
C280.65006 (19)1.0544 (2)0.22560 (9)0.0271 (4)
H28A0.73351.01140.25700.041*
H28B0.67321.11420.18510.041*
H28C0.63810.97770.20860.041*
C290.48855 (18)1.07665 (19)0.39727 (8)0.0225 (3)
H29A0.44631.02240.43370.027*
H29B0.43681.17890.40600.027*
C300.65814 (18)1.01798 (19)0.40554 (9)0.0249 (3)
H30A0.71000.91600.39820.037*
H30B0.67291.02760.45330.037*
H30C0.70051.07250.37040.037*
N10.61078 (14)0.57026 (14)0.27235 (7)0.0171 (3)
H1N0.5531 (17)0.6437 (14)0.2944 (9)0.021*
N20.86543 (14)0.56526 (15)0.20521 (7)0.0189 (3)
N30.69355 (14)0.51275 (14)0.13357 (7)0.0180 (3)
N40.35276 (14)0.98215 (14)0.23445 (7)0.0165 (3)
H4N0.4223 (16)0.9119 (15)0.2137 (9)0.020*
N50.20814 (14)1.03206 (14)0.36923 (7)0.0177 (3)
N60.45443 (14)1.06710 (14)0.32700 (7)0.0183 (3)
O10.72094 (12)0.32468 (12)0.28206 (6)0.0228 (2)
O20.59113 (12)0.76509 (12)0.17011 (6)0.0199 (2)
O30.16060 (13)1.20949 (12)0.21337 (6)0.0245 (3)
O40.45592 (12)0.80999 (12)0.34521 (5)0.0186 (2)
F10.30436 (11)0.58847 (12)0.30978 (5)0.0313 (2)
F20.73617 (10)0.28522 (11)0.43493 (5)0.0266 (2)
F30.20325 (15)0.87869 (13)0.14729 (6)0.0432 (3)
F40.33580 (13)1.26003 (13)0.08068 (6)0.0384 (3)
P10.68900 (4)0.61027 (4)0.19235 (2)0.01603 (10)
P20.37136 (4)0.96644 (4)0.32203 (2)0.01492 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0241 (7)0.0228 (9)0.0202 (8)0.0111 (7)0.0022 (6)0.0009 (6)
C20.0225 (8)0.0293 (10)0.0290 (9)0.0122 (7)0.0056 (7)0.0077 (7)
C30.0343 (9)0.0293 (10)0.0222 (8)0.0206 (8)0.0085 (7)0.0075 (7)
C40.0362 (9)0.0242 (9)0.0151 (8)0.0175 (7)0.0023 (6)0.0022 (6)
C50.0233 (7)0.0191 (8)0.0181 (8)0.0115 (6)0.0029 (6)0.0027 (6)
C60.0224 (7)0.0169 (8)0.0160 (7)0.0108 (6)0.0015 (6)0.0038 (6)
C70.0191 (7)0.0192 (8)0.0154 (7)0.0096 (6)0.0019 (6)0.0020 (6)
C80.0216 (7)0.0227 (9)0.0217 (8)0.0100 (7)0.0053 (6)0.0031 (7)
C90.0317 (9)0.0364 (10)0.0223 (9)0.0188 (8)0.0031 (7)0.0055 (7)
C100.0231 (7)0.0316 (10)0.0215 (8)0.0158 (7)0.0054 (6)0.0067 (7)
C110.0285 (8)0.0330 (10)0.0279 (9)0.0196 (8)0.0043 (7)0.0040 (8)
C120.0224 (7)0.0177 (8)0.0209 (8)0.0078 (6)0.0003 (6)0.0059 (6)
C130.0322 (9)0.0344 (10)0.0230 (9)0.0098 (8)0.0039 (7)0.0123 (8)
C140.0227 (7)0.0240 (9)0.0215 (8)0.0077 (7)0.0047 (6)0.0049 (7)
C150.0364 (10)0.0485 (13)0.0491 (13)0.0273 (10)0.0150 (9)0.0046 (10)
C160.0372 (9)0.0265 (9)0.0233 (9)0.0161 (8)0.0065 (7)0.0008 (7)
C170.0511 (11)0.0352 (11)0.0292 (10)0.0165 (9)0.0129 (9)0.0093 (8)
C180.0377 (10)0.0445 (12)0.0172 (9)0.0044 (9)0.0067 (7)0.0080 (8)
C190.0290 (9)0.0413 (11)0.0182 (8)0.0102 (8)0.0003 (7)0.0036 (8)
C200.0237 (8)0.0267 (9)0.0224 (8)0.0106 (7)0.0029 (6)0.0011 (7)
C210.0193 (7)0.0193 (8)0.0155 (7)0.0066 (6)0.0031 (6)0.0004 (6)
C220.0192 (7)0.0199 (8)0.0157 (7)0.0104 (6)0.0025 (6)0.0008 (6)
C230.0227 (7)0.0232 (9)0.0274 (9)0.0134 (7)0.0050 (6)0.0020 (7)
C240.0268 (8)0.0357 (11)0.0443 (11)0.0200 (8)0.0013 (8)0.0098 (9)
C250.0191 (7)0.0183 (8)0.0190 (8)0.0058 (6)0.0011 (6)0.0026 (6)
C260.0238 (8)0.0241 (9)0.0233 (8)0.0072 (7)0.0028 (6)0.0062 (7)
C270.0279 (8)0.0208 (8)0.0191 (8)0.0152 (7)0.0014 (6)0.0003 (6)
C280.0313 (8)0.0361 (10)0.0206 (8)0.0223 (8)0.0057 (7)0.0054 (7)
C290.0243 (8)0.0308 (9)0.0167 (8)0.0148 (7)0.0006 (6)0.0074 (7)
C300.0245 (8)0.0282 (9)0.0234 (8)0.0119 (7)0.0040 (6)0.0043 (7)
N10.0203 (6)0.0154 (7)0.0149 (6)0.0078 (5)0.0019 (5)0.0033 (5)
N20.0201 (6)0.0223 (7)0.0165 (6)0.0118 (5)0.0014 (5)0.0032 (5)
N30.0189 (6)0.0175 (7)0.0165 (6)0.0066 (5)0.0011 (5)0.0035 (5)
N40.0191 (6)0.0161 (7)0.0132 (6)0.0070 (5)0.0002 (5)0.0024 (5)
N50.0182 (6)0.0163 (7)0.0177 (6)0.0080 (5)0.0024 (5)0.0020 (5)
N60.0216 (6)0.0233 (7)0.0140 (6)0.0131 (5)0.0006 (5)0.0042 (5)
O10.0262 (6)0.0170 (6)0.0224 (6)0.0087 (5)0.0039 (5)0.0031 (5)
O20.0230 (5)0.0173 (6)0.0169 (5)0.0081 (5)0.0025 (4)0.0013 (4)
O30.0257 (6)0.0207 (6)0.0204 (6)0.0039 (5)0.0031 (4)0.0031 (5)
O40.0222 (5)0.0169 (6)0.0144 (5)0.0071 (4)0.0006 (4)0.0016 (4)
F10.0239 (5)0.0356 (6)0.0264 (5)0.0089 (4)0.0057 (4)0.0063 (4)
F20.0233 (5)0.0304 (6)0.0250 (5)0.0113 (4)0.0063 (4)0.0012 (4)
F30.0746 (8)0.0430 (7)0.0328 (6)0.0446 (7)0.0103 (6)0.0027 (5)
F40.0549 (7)0.0427 (7)0.0309 (6)0.0362 (6)0.0027 (5)0.0042 (5)
P10.01849 (18)0.0158 (2)0.01376 (19)0.00829 (15)0.00112 (14)0.00177 (15)
P20.01601 (17)0.0156 (2)0.01290 (19)0.00705 (15)0.00050 (13)0.00145 (15)
Geometric parameters (Å, º) top
C1—F11.3536 (19)C18—C191.376 (3)
C1—C21.379 (2)C18—H180.9500
C1—C61.392 (2)C19—C201.377 (2)
C2—C31.379 (3)C19—H190.9500
C2—H20.9500C20—F41.355 (2)
C3—C41.388 (2)C20—C211.378 (2)
C3—H30.9500C21—C221.509 (2)
C4—C51.376 (2)C22—O31.2154 (19)
C4—H40.9500C22—N41.3585 (19)
C5—F21.3551 (18)C23—N51.4791 (19)
C5—C61.386 (2)C23—C241.520 (3)
C6—C71.510 (2)C23—H23A0.9900
C7—O11.2172 (19)C23—H23B0.9900
C7—N11.359 (2)C24—H24A0.9800
C8—N21.468 (2)C24—H24B0.9800
C8—C91.523 (2)C24—H24C0.9800
C8—H8A0.9900C25—N51.469 (2)
C8—H8B0.9900C25—C261.520 (2)
C9—H9A0.9800C25—H25A0.9900
C9—H9B0.9800C25—H25B0.9900
C9—H9C0.9800C26—H26A0.9800
C10—N21.4708 (19)C26—H26B0.9800
C10—C111.516 (2)C26—H26C0.9800
C10—H10A0.9900C27—N61.4730 (19)
C10—H10B0.9900C27—C281.523 (2)
C11—H11A0.9800C27—H27A0.9900
C11—H11B0.9800C27—H27B0.9900
C11—H11C0.9800C28—H28A0.9800
C12—N31.474 (2)C28—H28B0.9800
C12—C131.519 (2)C28—H28C0.9800
C12—H12A0.9900C29—N61.470 (2)
C12—H12B0.9900C29—C301.523 (2)
C13—H13A0.9800C29—H29A0.9900
C13—H13B0.9800C29—H29B0.9900
C13—H13C0.9800C30—H30A0.9800
C14—N31.4814 (19)C30—H30B0.9800
C14—C151.512 (2)C30—H30C0.9800
C14—H14A0.9900N1—P11.6919 (13)
C14—H14B0.9900N1—H1N0.862 (9)
C15—H15A0.9800N2—P11.6320 (13)
C15—H15B0.9800N3—P11.6369 (13)
C15—H15C0.9800N4—P21.6918 (13)
C16—F31.352 (2)N4—H4N0.859 (9)
C16—C171.376 (3)N5—P21.6378 (13)
C16—C211.385 (2)N6—P21.6288 (13)
C17—C181.379 (3)O2—P11.4845 (12)
C17—H170.9500O4—P21.4816 (12)
F1—C1—C2118.38 (14)C20—C21—C16115.50 (15)
F1—C1—C6118.15 (14)C20—C21—C22121.32 (14)
C2—C1—C6123.47 (15)C16—C21—C22123.16 (14)
C1—C2—C3118.02 (15)O3—C22—N4125.12 (14)
C1—C2—H2121.0O3—C22—C21120.69 (14)
C3—C2—H2121.0N4—C22—C21114.18 (13)
C2—C3—C4121.51 (15)N5—C23—C24113.50 (14)
C2—C3—H3119.2N5—C23—H23A108.9
C4—C3—H3119.2C24—C23—H23A108.9
C5—C4—C3117.68 (15)N5—C23—H23B108.9
C5—C4—H4121.2C24—C23—H23B108.9
C3—C4—H4121.2H23A—C23—H23B107.7
F2—C5—C4118.41 (14)C23—C24—H24A109.5
F2—C5—C6117.69 (13)C23—C24—H24B109.5
C4—C5—C6123.88 (15)H24A—C24—H24B109.5
C5—C6—C1115.43 (14)C23—C24—H24C109.5
C5—C6—C7121.28 (13)H24A—C24—H24C109.5
C1—C6—C7123.18 (14)H24B—C24—H24C109.5
O1—C7—N1124.48 (14)N5—C25—C26113.31 (13)
O1—C7—C6120.57 (14)N5—C25—H25A108.9
N1—C7—C6114.94 (13)C26—C25—H25A108.9
N2—C8—C9114.42 (14)N5—C25—H25B108.9
N2—C8—H8A108.7C26—C25—H25B108.9
C9—C8—H8A108.7H25A—C25—H25B107.7
N2—C8—H8B108.7C25—C26—H26A109.5
C9—C8—H8B108.7C25—C26—H26B109.5
H8A—C8—H8B107.6H26A—C26—H26B109.5
C8—C9—H9A109.5C25—C26—H26C109.5
C8—C9—H9B109.5H26A—C26—H26C109.5
H9A—C9—H9B109.5H26B—C26—H26C109.5
C8—C9—H9C109.5N6—C27—C28114.02 (14)
H9A—C9—H9C109.5N6—C27—H27A108.7
H9B—C9—H9C109.5C28—C27—H27A108.7
N2—C10—C11113.87 (13)N6—C27—H27B108.7
N2—C10—H10A108.8C28—C27—H27B108.7
C11—C10—H10A108.8H27A—C27—H27B107.6
N2—C10—H10B108.8C27—C28—H28A109.5
C11—C10—H10B108.8C27—C28—H28B109.5
H10A—C10—H10B107.7H28A—C28—H28B109.5
C10—C11—H11A109.5C27—C28—H28C109.5
C10—C11—H11B109.5H28A—C28—H28C109.5
H11A—C11—H11B109.5H28B—C28—H28C109.5
C10—C11—H11C109.5N6—C29—C30113.61 (13)
H11A—C11—H11C109.5N6—C29—H29A108.8
H11B—C11—H11C109.5C30—C29—H29A108.8
N3—C12—C13112.16 (14)N6—C29—H29B108.8
N3—C12—H12A109.2C30—C29—H29B108.8
C13—C12—H12A109.2H29A—C29—H29B107.7
N3—C12—H12B109.2C29—C30—H30A109.5
C13—C12—H12B109.2C29—C30—H30B109.5
H12A—C12—H12B107.9H30A—C30—H30B109.5
C12—C13—H13A109.5C29—C30—H30C109.5
C12—C13—H13B109.5H30A—C30—H30C109.5
H13A—C13—H13B109.5H30B—C30—H30C109.5
C12—C13—H13C109.5C7—N1—P1126.89 (11)
H13A—C13—H13C109.5C7—N1—H1N118.5 (12)
H13B—C13—H13C109.5P1—N1—H1N114.6 (12)
N3—C14—C15113.90 (14)C8—N2—C10116.67 (12)
N3—C14—H14A108.8C8—N2—P1124.21 (10)
C15—C14—H14A108.8C10—N2—P1118.78 (11)
N3—C14—H14B108.8C12—N3—C14116.44 (12)
C15—C14—H14B108.8C12—N3—P1123.86 (10)
H14A—C14—H14B107.7C14—N3—P1118.29 (10)
C14—C15—H15A109.5C22—N4—P2128.35 (11)
C14—C15—H15B109.5C22—N4—H4N117.5 (12)
H15A—C15—H15B109.5P2—N4—H4N113.8 (12)
C14—C15—H15C109.5C25—N5—C23114.57 (12)
H15A—C15—H15C109.5C25—N5—P2123.35 (10)
H15B—C15—H15C109.5C23—N5—P2118.53 (11)
F3—C16—C17118.90 (16)C29—N6—C27116.48 (12)
F3—C16—C21117.75 (15)C29—N6—P2118.25 (10)
C17—C16—C21123.34 (17)C27—N6—P2125.25 (10)
C16—C17—C18118.34 (18)O2—P1—N2116.97 (7)
C16—C17—H17120.8O2—P1—N3109.95 (7)
C18—C17—H17120.8N2—P1—N3106.97 (7)
C19—C18—C17120.89 (17)O2—P1—N1105.64 (6)
C19—C18—H18119.6N2—P1—N1105.14 (7)
C17—C18—H18119.6N3—P1—N1112.19 (7)
C18—C19—C20118.29 (17)O4—P2—N6117.09 (7)
C18—C19—H19120.9O4—P2—N5109.45 (6)
C20—C19—H19120.9N6—P2—N5106.67 (7)
F4—C20—C19118.80 (15)O4—P2—N4106.03 (6)
F4—C20—C21117.56 (15)N6—P2—N4104.30 (6)
C19—C20—C21123.62 (17)N5—P2—N4113.43 (7)
F1—C1—C2—C3178.31 (15)C13—C12—N3—P1131.07 (13)
C6—C1—C2—C30.4 (3)C15—C14—N3—C1264.02 (19)
C1—C2—C3—C40.4 (3)C15—C14—N3—P1102.97 (16)
C2—C3—C4—C50.2 (2)O3—C22—N4—P22.2 (2)
C3—C4—C5—F2178.75 (14)C21—C22—N4—P2179.21 (10)
C3—C4—C5—C60.0 (2)C26—C25—N5—C2378.67 (16)
F2—C5—C6—C1178.73 (13)C26—C25—N5—P2122.95 (13)
C4—C5—C6—C10.0 (2)C24—C23—N5—C2582.79 (17)
F2—C5—C6—C75.0 (2)C24—C23—N5—P276.70 (17)
C4—C5—C6—C7176.22 (14)C30—C29—N6—C2761.26 (19)
F1—C1—C6—C5178.52 (14)C30—C29—N6—P2117.10 (13)
C2—C1—C6—C50.2 (2)C28—C27—N6—C29100.51 (16)
F1—C1—C6—C72.4 (2)C28—C27—N6—P277.73 (16)
C2—C1—C6—C7176.33 (15)C8—N2—P1—O2108.18 (13)
C5—C6—C7—O153.3 (2)C10—N2—P1—O264.95 (13)
C1—C6—C7—O1122.68 (17)C8—N2—P1—N3128.08 (13)
C5—C6—C7—N1126.92 (15)C10—N2—P1—N358.79 (13)
C1—C6—C7—N157.1 (2)C8—N2—P1—N18.64 (14)
F3—C16—C17—C18179.22 (17)C10—N2—P1—N1178.24 (12)
C21—C16—C17—C181.1 (3)C12—N3—P1—O2158.74 (11)
C16—C17—C18—C190.4 (3)C14—N3—P1—O235.31 (13)
C17—C18—C19—C200.6 (3)C12—N3—P1—N230.77 (13)
C18—C19—C20—F4179.12 (16)C14—N3—P1—N2163.28 (11)
C18—C19—C20—C210.9 (3)C12—N3—P1—N184.02 (13)
F4—C20—C21—C16178.46 (14)C14—N3—P1—N181.93 (12)
C19—C20—C21—C160.2 (2)C7—N1—P1—O2158.35 (12)
F4—C20—C21—C222.9 (2)C7—N1—P1—N277.34 (14)
C19—C20—C21—C22178.81 (15)C7—N1—P1—N338.56 (15)
F3—C16—C21—C20179.52 (15)C29—N6—P2—O462.89 (13)
C17—C16—C21—C200.8 (3)C27—N6—P2—O4115.31 (13)
F3—C16—C21—C221.9 (2)C29—N6—P2—N560.04 (13)
C17—C16—C21—C22177.75 (17)C27—N6—P2—N5121.76 (13)
C20—C21—C22—O360.4 (2)C29—N6—P2—N4179.66 (11)
C16—C21—C22—O3118.08 (18)C27—N6—P2—N41.46 (14)
C20—C21—C22—N4118.26 (16)C25—N5—P2—O4165.15 (11)
C16—C21—C22—N463.24 (19)C23—N5—P2—O437.27 (13)
O1—C7—N1—P19.5 (2)C25—N5—P2—N637.57 (14)
C6—C7—N1—P1170.31 (10)C23—N5—P2—N6164.85 (11)
C9—C8—N2—C1098.29 (16)C25—N5—P2—N476.67 (13)
C9—C8—N2—P174.97 (16)C23—N5—P2—N480.91 (13)
C11—C10—N2—C861.34 (19)C22—N4—P2—O4161.18 (12)
C11—C10—N2—P1112.30 (14)C22—N4—P2—N674.62 (14)
C13—C12—N3—C1462.74 (17)C22—N4—P2—N541.03 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4N···O20.86 (1)1.89 (1)2.7429 (17)173 (2)
N1—H1N···O40.86 (1)1.93 (1)2.7828 (17)170 (2)
C4—H4···O4i0.952.343.238 (2)157
C19—H19···O2ii0.952.433.230 (2)142
C27—H27A···O1iii0.992.673.5023 (19)142
C27—H27B···O30.992.593.418 (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
C13H20F2N3O3PDx = 1.382 Mg m3
Mr = 335.29Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P212121Cell parameters from 2764 reflections
a = 8.7127 (4) Åθ = 4.8–64.9°
b = 10.9675 (8) ŵ = 1.86 mm1
c = 16.8649 (9) ÅT = 100 K
V = 1611.55 (16) Å3BLOCK, colourless
Z = 40.15 × 0.10 × 0.08 mm
F(000) = 704
Data collection top
Bruker APEX-II CCD
diffractometer
2606 independent reflections
Radiation source: fine-focus sealed tube2204 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
φ and ω scansθmax = 65.2°, θmin = 4.8°
Absorption correction: multi-scan
SADABS (Sheldrick, 2004)
h = 109
Tmin = 0.768, Tmax = 0.866k = 1212
5564 measured reflectionsl = 1619
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.112 w = 1/[σ2(Fo2) + (0.0637P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
2606 reflectionsΔρmax = 0.23 e Å3
213 parametersΔρmin = 0.28 e Å3
4 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.04 (4)
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
xyzUiso*/Ueq
P10.31120 (8)0.24796 (10)0.43973 (5)0.0243 (2)
F10.4534 (3)0.6434 (2)0.44471 (12)0.0450 (6)
F20.4502 (2)0.4419 (2)0.68872 (11)0.0351 (5)
O10.2008 (2)0.4597 (2)0.53800 (13)0.0285 (6)
O1S0.1085 (3)0.3996 (4)0.37612 (16)0.0485 (8)
H1S0.148 (5)0.380 (4)0.4213 (14)0.058*
O20.2260 (2)0.1668 (2)0.49445 (13)0.0294 (6)
N10.4083 (3)0.3550 (3)0.49294 (16)0.0255 (7)
H1N0.5075 (12)0.355 (3)0.493 (2)0.031*
N20.2082 (3)0.3171 (3)0.37509 (16)0.0286 (7)
H2N0.1130 (16)0.331 (3)0.386 (2)0.034*
N30.4444 (3)0.1823 (3)0.38705 (16)0.0238 (7)
H3N0.506 (3)0.135 (3)0.4133 (19)0.029*
C10.4990 (4)0.6377 (4)0.5217 (2)0.0341 (9)
C1S0.0844 (5)0.5129 (5)0.3951 (3)0.0557 (13)
H1D0.04460.55700.34890.083*
H1E0.00940.51690.43830.083*
H1C0.18100.55020.41230.083*
C20.5931 (4)0.7279 (4)0.5509 (2)0.0443 (11)
H2A0.62680.79310.51810.053*
C30.6371 (4)0.7204 (4)0.6295 (3)0.0404 (11)
H3A0.70100.78210.65120.048*
C40.5900 (4)0.6248 (4)0.6773 (2)0.0338 (9)
H4A0.62030.61990.73130.041*
C50.4979 (4)0.5375 (4)0.6437 (2)0.0260 (8)
C60.4477 (3)0.5408 (3)0.56596 (19)0.0242 (7)
C70.3397 (3)0.4482 (4)0.53180 (18)0.0244 (8)
C80.2847 (4)0.3867 (3)0.31132 (19)0.0277 (8)
H8A0.34240.45560.33480.033*
H8B0.20620.42080.27510.033*
C90.3944 (4)0.3058 (3)0.2645 (2)0.0244 (8)
C100.5147 (3)0.2520 (4)0.32041 (18)0.0241 (7)
H10A0.58320.19720.29000.029*
H10B0.57820.31890.34230.029*
C110.3066 (4)0.2048 (3)0.22205 (19)0.0294 (8)
H11A0.23400.24100.18450.044*
H11B0.25040.15590.26110.044*
H11C0.37910.15260.19340.044*
C120.4755 (4)0.3854 (4)0.2035 (2)0.0323 (9)
H12A0.39920.42310.16860.048*
H12B0.54560.33510.17200.048*
H12C0.53390.44920.23080.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0110 (3)0.0431 (5)0.0187 (4)0.0022 (4)0.0000 (3)0.0051 (4)
F10.0471 (12)0.0654 (16)0.0224 (11)0.0139 (12)0.0014 (10)0.0102 (12)
F20.0370 (11)0.0458 (14)0.0225 (11)0.0038 (11)0.0053 (9)0.0027 (10)
O10.0132 (10)0.0473 (15)0.0249 (13)0.0013 (11)0.0033 (9)0.0073 (12)
O1S0.0302 (15)0.085 (3)0.0300 (16)0.0090 (17)0.0043 (13)0.0054 (18)
O20.0159 (11)0.0503 (17)0.0222 (12)0.0031 (11)0.0001 (9)0.0024 (11)
N10.0118 (12)0.0420 (18)0.0226 (15)0.0046 (13)0.0004 (11)0.0048 (14)
N20.0140 (12)0.053 (2)0.0191 (15)0.0068 (14)0.0001 (12)0.0068 (14)
N30.0155 (13)0.0371 (18)0.0187 (15)0.0028 (13)0.0008 (11)0.0004 (14)
C10.0241 (17)0.058 (3)0.0199 (19)0.0034 (18)0.0016 (15)0.001 (2)
C1S0.038 (2)0.076 (4)0.053 (3)0.007 (3)0.004 (2)0.018 (3)
C20.035 (2)0.054 (3)0.043 (2)0.015 (2)0.0015 (18)0.006 (2)
C30.0254 (17)0.048 (3)0.048 (2)0.0083 (18)0.0028 (18)0.012 (2)
C40.0191 (17)0.054 (3)0.028 (2)0.0075 (18)0.0043 (15)0.0066 (19)
C50.0166 (15)0.038 (2)0.0238 (18)0.0042 (16)0.0026 (13)0.0012 (18)
C60.0150 (14)0.040 (2)0.0175 (17)0.0020 (15)0.0034 (14)0.0025 (17)
C70.0163 (16)0.043 (2)0.0135 (16)0.0031 (15)0.0028 (12)0.0010 (17)
C80.0197 (17)0.040 (2)0.0237 (18)0.0057 (16)0.0040 (14)0.0047 (16)
C90.0169 (15)0.037 (2)0.0188 (17)0.0020 (15)0.0011 (14)0.0016 (16)
C100.0158 (14)0.0356 (19)0.0210 (17)0.0020 (17)0.0004 (12)0.0034 (19)
C110.0234 (16)0.044 (2)0.0207 (18)0.0000 (17)0.0002 (15)0.0041 (16)
C120.0253 (18)0.038 (2)0.033 (2)0.0014 (17)0.0046 (16)0.0033 (19)
Geometric parameters (Å, º) top
P1—O21.481 (3)C2—H2A0.9500
P1—N21.603 (3)C3—C41.385 (6)
P1—N31.629 (3)C3—H3A0.9500
P1—N11.703 (3)C4—C51.372 (5)
F1—C11.359 (4)C4—H4A0.9500
F2—C51.359 (4)C5—C61.383 (5)
O1—C71.221 (4)C6—C71.499 (5)
O1S—C1S1.300 (6)C8—C91.524 (5)
O1S—H1S0.863 (10)C8—H8A0.9900
N1—C71.354 (4)C8—H8B0.9900
N1—H1N0.864 (10)C9—C121.523 (5)
N2—C81.478 (4)C9—C111.524 (5)
N2—H2N0.862 (10)C9—C101.529 (4)
N3—C101.491 (4)C10—H10A0.9900
N3—H3N0.869 (10)C10—H10B0.9900
C1—C61.374 (5)C11—H11A0.9800
C1—C21.376 (5)C11—H11B0.9800
C1S—H1D0.9800C11—H11C0.9800
C1S—H1E0.9800C12—H12A0.9800
C1S—H1C0.9800C12—H12B0.9800
C2—C31.382 (6)C12—H12C0.9800
O2—P1—N2115.28 (14)C1—C6—C5115.6 (3)
O2—P1—N3115.55 (16)C1—C6—C7121.3 (3)
N2—P1—N3103.71 (15)C5—C6—C7123.0 (3)
O2—P1—N1109.57 (14)O1—C7—N1123.9 (3)
N2—P1—N1108.10 (16)O1—C7—C6121.3 (3)
N3—P1—N1103.77 (14)N1—C7—C6114.8 (3)
C1S—O1S—H1S95 (3)N2—C8—C9111.0 (3)
C7—N1—P1123.8 (2)N2—C8—H8A109.4
C7—N1—H1N116 (3)C9—C8—H8A109.4
P1—N1—H1N120 (2)N2—C8—H8B109.4
C8—N2—P1119.1 (2)C9—C8—H8B109.4
C8—N2—H2N120 (3)H8A—C8—H8B108.0
P1—N2—H2N119 (3)C12—C9—C11109.4 (3)
C10—N3—P1118.5 (2)C12—C9—C8107.9 (3)
C10—N3—H3N116 (2)C11—C9—C8110.6 (3)
P1—N3—H3N115 (2)C12—C9—C10108.6 (3)
F1—C1—C6117.3 (3)C11—C9—C10110.7 (3)
F1—C1—C2118.9 (4)C8—C9—C10109.6 (3)
C6—C1—C2123.7 (4)N3—C10—C9112.4 (2)
O1S—C1S—H1D109.5N3—C10—H10A109.1
O1S—C1S—H1E109.5C9—C10—H10A109.1
H1D—C1S—H1E109.5N3—C10—H10B109.1
O1S—C1S—H1C109.5C9—C10—H10B109.1
H1D—C1S—H1C109.5H10A—C10—H10B107.9
H1E—C1S—H1C109.5C9—C11—H11A109.5
C1—C2—C3117.7 (4)C9—C11—H11B109.5
C1—C2—H2A121.1H11A—C11—H11B109.5
C3—C2—H2A121.1C9—C11—H11C109.5
C2—C3—C4121.4 (4)H11A—C11—H11C109.5
C2—C3—H3A119.3H11B—C11—H11C109.5
C4—C3—H3A119.3C9—C12—H12A109.5
C5—C4—C3117.5 (3)C9—C12—H12B109.5
C5—C4—H4A121.3H12A—C12—H12B109.5
C3—C4—H4A121.3C9—C12—H12C109.5
F2—C5—C4119.1 (3)H12A—C12—H12C109.5
F2—C5—C6116.9 (3)H12B—C12—H12C109.5
C4—C5—C6123.9 (4)
O2—P1—N1—C770.9 (3)F2—C5—C6—C1179.4 (3)
N2—P1—N1—C755.4 (3)C4—C5—C6—C11.4 (5)
N3—P1—N1—C7165.1 (3)F2—C5—C6—C72.8 (5)
O2—P1—N2—C8171.8 (2)C4—C5—C6—C7176.3 (3)
N3—P1—N2—C844.5 (3)P1—N1—C7—O16.1 (5)
N1—P1—N2—C865.2 (3)P1—N1—C7—C6172.4 (2)
O2—P1—N3—C10168.8 (2)C1—C6—C7—O191.5 (4)
N2—P1—N3—C1041.6 (3)C5—C6—C7—O186.2 (4)
N1—P1—N3—C1071.3 (3)C1—C6—C7—N187.0 (4)
F1—C1—C2—C3179.6 (3)C5—C6—C7—N195.3 (4)
C6—C1—C2—C30.5 (6)P1—N2—C8—C956.6 (4)
C1—C2—C3—C40.8 (6)N2—C8—C9—C12176.6 (3)
C2—C3—C4—C50.0 (6)N2—C8—C9—C1163.8 (3)
C3—C4—C5—F2179.6 (3)N2—C8—C9—C1058.5 (4)
C3—C4—C5—C61.2 (5)P1—N3—C10—C951.6 (4)
F1—C1—C6—C5179.3 (3)C12—C9—C10—N3174.4 (3)
C2—C1—C6—C50.5 (5)C11—C9—C10—N365.5 (4)
F1—C1—C6—C72.9 (5)C8—C9—C10—N356.8 (4)
C2—C1—C6—C7177.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1S—H1S···O2i0.86 (1)1.87 (2)2.716 (4)167 (4)
N1—H1N···O2ii0.86 (1)1.93 (1)2.786 (3)171 (4)
N2—H2N···O1S0.86 (1)2.08 (2)2.904 (4)160 (3)
N3—H3N···O1ii0.87 (1)2.15 (1)3.003 (4)166 (3)
C4—H4A···O1Siii0.952.453.368 (5)161
C8—H8B···F2iv0.992.503.463 (4)165
Symmetry codes: (i) x1/2, 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, z1/2.
(III) top
Crystal data top
C16H18NO4PF(000) = 336
Mr = 319.28Dx = 1.328 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 600 reflections
a = 6.4231 (2) Åθ = 1–14°
b = 9.1119 (3) ŵ = 0.19 mm1
c = 13.6799 (4) ÅT = 293 K
β = 94.137 (2)°Block, colourless
V = 798.55 (4) Å30.3 × 0.25 × 0.19 mm
Z = 2
Data collection top
KappaCCD
diffractometer
3194 independent reflections
Radiation source: Enraf Nonius FR5902565 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
Detector resolution: 9 pixels mm-1θmax = 27.5°, θmin = 3.0°
CCD rotation images, thick slices scansh = 88
Absorption correction: multi-scan
SADABS (Sheldrick, 2004)
k = 1110
Tmin = 0.941, Tmax = 0.968l = 1717
6909 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.107 w = 1/[σ2(Fo2) + (0.0512P)2 + 0.0708P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.006
3194 reflectionsΔρmax = 0.16 e Å3
199 parametersΔρmin = 0.21 e Å3
1 restraintAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute 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
xyzUiso*/Ueq
C10.2228 (4)0.9014 (3)0.61709 (17)0.0474 (6)
C20.3714 (4)0.9299 (3)0.55152 (17)0.0555 (6)
H20.50030.88310.55710.067*
C30.3229 (5)1.0303 (4)0.47717 (19)0.0655 (8)
H30.42141.05140.43260.079*
C40.1348 (5)1.0983 (4)0.4683 (2)0.0703 (9)
H40.10521.16550.4180.084*
C50.0135 (6)1.0677 (4)0.5342 (2)0.0742 (9)
H50.14331.11320.52740.089*
C60.0308 (4)0.9699 (3)0.6100 (2)0.0596 (7)
H60.06680.95060.65530.072*
C70.4687 (4)0.5295 (3)0.78227 (16)0.0518 (6)
C80.6680 (5)0.4773 (4)0.7972 (2)0.0647 (8)
H80.76930.53110.83370.078*
C90.7168 (6)0.3428 (4)0.7570 (3)0.0833 (10)
H90.85150.30570.76720.1*
C100.5693 (8)0.2648 (4)0.7029 (3)0.0875 (11)
H100.60340.17470.67650.105*
C110.3728 (6)0.3181 (5)0.6875 (2)0.0824 (10)
H110.2730.26430.65020.099*
C120.3185 (5)0.4529 (4)0.7271 (2)0.0673 (8)
H120.18390.48980.71620.081*
C130.4307 (4)1.0351 (3)0.9151 (2)0.0615 (7)
H13A0.54441.07180.8790.074*
H13B0.48970.99320.97610.074*
C140.2880 (6)1.1571 (4)0.9359 (3)0.0813 (9)
H14A0.36351.22920.97680.098*
H14B0.24061.20460.87490.098*
C150.1249 (5)0.8751 (4)0.9017 (3)0.0796 (9)
H15A0.16230.81890.96060.096*
H15B0.04330.81230.85630.096*
C160.0010 (5)1.0032 (5)0.9265 (3)0.0897 (12)
H16A0.05641.04960.86630.108*
H16B0.11830.96990.96140.108*
N10.3152 (3)0.9220 (3)0.85728 (16)0.0543 (5)
O10.2603 (3)0.79354 (19)0.68948 (11)0.0538 (5)
O20.6307 (3)0.8671 (2)0.75590 (12)0.0590 (5)
O30.4142 (3)0.6600 (2)0.82887 (11)0.0592 (5)
O40.1120 (4)1.1077 (3)0.98403 (16)0.0775 (6)
P10.42539 (9)0.81767 (7)0.78057 (4)0.04627 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0561 (15)0.0371 (13)0.0482 (12)0.0006 (11)0.0012 (10)0.0043 (10)
C20.0641 (16)0.0505 (15)0.0523 (13)0.0070 (13)0.0082 (12)0.0022 (11)
C30.089 (2)0.0569 (18)0.0514 (14)0.0081 (17)0.0114 (14)0.0048 (13)
C40.095 (2)0.0570 (19)0.0569 (17)0.0137 (18)0.0072 (15)0.0054 (14)
C50.0687 (19)0.065 (2)0.087 (2)0.0187 (17)0.0129 (17)0.0019 (17)
C60.0525 (15)0.0577 (17)0.0687 (16)0.0033 (13)0.0051 (12)0.0042 (13)
C70.0750 (17)0.0407 (14)0.0405 (12)0.0026 (13)0.0088 (11)0.0044 (10)
C80.074 (2)0.0557 (18)0.0637 (15)0.0050 (15)0.0026 (14)0.0038 (14)
C90.095 (2)0.064 (2)0.092 (2)0.024 (2)0.0236 (19)0.0105 (17)
C100.129 (3)0.0487 (19)0.090 (2)0.002 (2)0.037 (2)0.0033 (16)
C110.114 (3)0.065 (2)0.0695 (17)0.029 (3)0.0121 (17)0.0119 (19)
C120.075 (2)0.065 (2)0.0629 (16)0.0127 (16)0.0066 (14)0.0014 (15)
C130.0605 (16)0.0595 (17)0.0646 (14)0.0058 (14)0.0050 (12)0.0111 (13)
C140.091 (2)0.062 (2)0.092 (2)0.0057 (18)0.0133 (19)0.0208 (18)
C150.0688 (18)0.072 (2)0.103 (2)0.0173 (16)0.0450 (17)0.0178 (18)
C160.0578 (18)0.121 (4)0.092 (2)0.005 (2)0.0159 (17)0.015 (2)
N10.0526 (12)0.0489 (13)0.0633 (12)0.0084 (10)0.0172 (10)0.0106 (10)
O10.0615 (10)0.0442 (11)0.0550 (9)0.0092 (9)0.0007 (7)0.0051 (8)
O20.0479 (9)0.0705 (13)0.0595 (9)0.0014 (9)0.0112 (7)0.0008 (9)
O30.0887 (14)0.0451 (10)0.0451 (9)0.0067 (10)0.0129 (9)0.0025 (8)
O40.0787 (14)0.0814 (16)0.0738 (13)0.0186 (12)0.0155 (11)0.0179 (11)
P10.0502 (3)0.0422 (3)0.0472 (3)0.0003 (3)0.0087 (2)0.0005 (3)
Geometric parameters (Å, º) top
C1—C61.379 (4)C11—C121.396 (5)
C1—C21.381 (4)C11—H110.93
C1—O11.404 (3)C12—H120.93
C2—C31.387 (4)C13—N11.467 (3)
C2—H20.93C13—C141.482 (4)
C3—C41.355 (5)C13—H13A0.97
C3—H30.93C13—H13B0.97
C4—C51.387 (5)C14—O41.421 (4)
C4—H40.93C14—H14A0.97
C5—C61.381 (4)C14—H14B0.97
C5—H50.93C15—N11.467 (3)
C6—H60.93C15—C161.473 (5)
C7—C81.367 (4)C15—H15A0.97
C7—C121.372 (4)C15—H15B0.97
C7—O31.405 (3)C16—O41.404 (5)
C8—C91.388 (5)C16—H16A0.97
C8—H80.93C16—H16B0.97
C9—C101.359 (6)N1—P11.617 (2)
C9—H90.93O1—P11.5922 (17)
C10—C111.354 (5)O2—P11.4562 (18)
C10—H100.93O3—P11.585 (2)
C6—C1—C2121.7 (2)N1—C13—C14109.5 (2)
C6—C1—O1118.3 (2)N1—C13—H13A109.8
C2—C1—O1119.9 (2)C14—C13—H13A109.8
C1—C2—C3118.1 (3)N1—C13—H13B109.8
C1—C2—H2120.9C14—C13—H13B109.8
C3—C2—H2120.9H13A—C13—H13B108.2
C4—C3—C2121.3 (3)O4—C14—C13112.1 (3)
C4—C3—H3119.4O4—C14—H14A109.2
C2—C3—H3119.4C13—C14—H14A109.2
C3—C4—C5119.9 (3)O4—C14—H14B109.2
C3—C4—H4120C13—C14—H14B109.2
C5—C4—H4120H14A—C14—H14B107.9
C6—C5—C4120.3 (3)N1—C15—C16110.6 (3)
C6—C5—H5119.9N1—C15—H15A109.5
C4—C5—H5119.9C16—C15—H15A109.5
C1—C6—C5118.6 (3)N1—C15—H15B109.5
C1—C6—H6120.7C16—C15—H15B109.5
C5—C6—H6120.7H15A—C15—H15B108.1
C8—C7—C12121.2 (3)O4—C16—C15113.3 (3)
C8—C7—O3119.2 (2)O4—C16—H16A108.9
C12—C7—O3119.5 (3)C15—C16—H16A108.9
C7—C8—C9118.9 (3)O4—C16—H16B108.9
C7—C8—H8120.5C15—C16—H16B108.9
C9—C8—H8120.5H16A—C16—H16B107.7
C10—C9—C8120.6 (4)C15—N1—C13112.7 (2)
C10—C9—H9119.7C15—N1—P1120.96 (19)
C8—C9—H9119.7C13—N1—P1122.30 (17)
C11—C10—C9120.1 (4)C1—O1—P1121.74 (15)
C11—C10—H10119.9C7—O3—P1123.87 (14)
C9—C10—H10119.9C16—O4—C14110.6 (2)
C10—C11—C12120.7 (3)O2—P1—O3116.52 (11)
C10—C11—H11119.6O2—P1—O1115.12 (9)
C12—C11—H11119.6O3—P1—O198.82 (10)
C7—C12—C11118.4 (3)O2—P1—N1114.50 (11)
C7—C12—H12120.8O3—P1—N1103.13 (11)
C11—C12—H12120.8O1—P1—N1106.92 (11)
C6—C1—C2—C30.0 (4)C14—C13—N1—C1552.0 (4)
O1—C1—C2—C3175.8 (2)C14—C13—N1—P1150.5 (2)
C1—C2—C3—C40.4 (5)C6—C1—O1—P1112.4 (2)
C2—C3—C4—C50.1 (5)C2—C1—O1—P171.6 (3)
C3—C4—C5—C61.1 (5)C8—C7—O3—P192.8 (3)
C2—C1—C6—C51.0 (4)C12—C7—O3—P190.7 (3)
O1—C1—C6—C5175.0 (3)C15—C16—O4—C1457.4 (4)
C4—C5—C6—C11.5 (5)C13—C14—O4—C1659.0 (4)
C12—C7—C8—C91.3 (4)C7—O3—P1—O261.8 (2)
O3—C7—C8—C9175.2 (2)C7—O3—P1—O162.1 (2)
C7—C8—C9—C100.6 (5)C7—O3—P1—N1171.9 (2)
C8—C9—C10—C110.1 (5)C1—O1—P1—O250.3 (2)
C9—C10—C11—C120.3 (5)C1—O1—P1—O3175.21 (18)
C8—C7—C12—C111.1 (4)C1—O1—P1—N178.08 (19)
O3—C7—C12—C11175.3 (2)C15—N1—P1—O2169.9 (2)
C10—C11—C12—C70.3 (4)C13—N1—P1—O214.2 (3)
N1—C13—C14—O456.1 (3)C15—N1—P1—O342.3 (3)
N1—C15—C16—O453.1 (4)C13—N1—P1—O3113.4 (2)
C16—C15—N1—C1350.4 (4)C15—N1—P1—O161.4 (3)
C16—C15—N1—P1151.8 (2)C13—N1—P1—O1143.0 (2)
(IV) top
Crystal data top
C18H15BrNO3PZ = 2
Mr = 404.19F(000) = 408
Triclinic, P1Dx = 1.483 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.1842 (2) ÅCell parameters from 600 reflections
b = 10.2741 (2) Åθ = 1–14°
c = 10.7121 (3) ŵ = 2.37 mm1
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 FR5903259 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
Detector resolution: 9 pixels mm-1θmax = 27.5°, θmin = 3.8°
CCD rotation images, thick slices scansh = 1212
Absorption correction: multi-scan
SADABS (Sheldrick, 2004)
k = 1113
Tmin = 0.428, Tmax = 0.546l = 1313
11476 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0377P)2 + 0.7366P]
where P = (Fo2 + 2Fc2)/3
4019 reflections(Δ/σ)max < 0.001
221 parametersΔρmax = 0.75 e Å3
1 restraintΔρmin = 0.90 e Å3
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
xyzUiso*/Ueq
C11.1855 (3)0.7708 (3)0.7538 (3)0.0413 (6)
C21.1072 (4)0.6164 (4)0.7455 (4)0.0661 (9)
H21.00110.5510.70680.079*
C31.1886 (5)0.5588 (5)0.7956 (5)0.0779 (12)
H31.13720.45430.79130.093*
C41.3449 (5)0.6561 (5)0.8516 (4)0.0695 (10)
H41.39910.61750.8860.083*
C51.4220 (4)0.8095 (5)0.8576 (4)0.0695 (10)
H51.52830.87440.89510.083*
C61.3416 (4)0.8688 (4)0.8075 (3)0.0565 (8)
H61.39310.97270.81060.068*
C70.8986 (3)1.0471 (3)0.6995 (3)0.0394 (6)
C80.8648 (4)1.0803 (4)0.5919 (3)0.0523 (7)
H80.89191.04680.51210.063*
C90.7902 (5)1.1637 (5)0.6026 (4)0.0727 (11)
H90.76651.18630.52950.087*
C100.7506 (5)1.2137 (5)0.7194 (4)0.0782 (12)
H100.70121.27120.72620.094*
C110.7836 (6)1.1790 (6)0.8259 (4)0.0812 (13)
H110.75571.21230.90530.097*
C120.8580 (5)1.0951 (5)0.8176 (4)0.0671 (10)
H120.88031.07140.89050.081*
C130.7601 (3)0.6365 (3)0.7361 (3)0.0371 (5)
C140.7427 (3)0.5713 (4)0.5969 (3)0.0478 (7)
H140.81590.62830.55770.057*
C150.6151 (4)0.4201 (4)0.5164 (3)0.0565 (8)
H150.60390.37660.42320.068*
C160.5052 (4)0.3336 (4)0.5718 (3)0.0541 (8)
H160.42050.23230.51740.065*
C170.5239 (3)0.4012 (3)0.7105 (3)0.0440 (6)
C180.6495 (3)0.5509 (3)0.7936 (3)0.0389 (6)
H180.660.59380.88680.047*
N10.8881 (2)0.7876 (3)0.8259 (2)0.0389 (5)
O11.1424 (2)1.0553 (2)0.91797 (18)0.0415 (4)
O21.1029 (2)0.8281 (2)0.69854 (18)0.0398 (4)
O30.9737 (2)0.9605 (2)0.67965 (19)0.0443 (4)
P11.03410 (7)0.91819 (7)0.79212 (7)0.03352 (16)
Br10.37725 (4)0.28278 (4)0.79178 (4)0.06523 (15)
H10.882 (4)0.829 (4)0.9082 (13)0.054 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0490 (15)0.0445 (14)0.0415 (14)0.0317 (13)0.0191 (12)0.0168 (12)
C20.0559 (19)0.0548 (19)0.104 (3)0.0343 (17)0.0261 (19)0.041 (2)
C30.080 (3)0.069 (2)0.120 (3)0.052 (2)0.038 (3)0.055 (2)
C40.093 (3)0.087 (3)0.064 (2)0.072 (3)0.026 (2)0.029 (2)
C50.063 (2)0.076 (3)0.062 (2)0.046 (2)0.0002 (17)0.0056 (18)
C60.0524 (18)0.0468 (17)0.0611 (19)0.0270 (15)0.0094 (15)0.0100 (14)
C70.0445 (14)0.0401 (14)0.0426 (14)0.0260 (12)0.0173 (11)0.0193 (11)
C80.0665 (19)0.0649 (19)0.0467 (16)0.0441 (17)0.0242 (14)0.0293 (15)
C90.098 (3)0.096 (3)0.070 (2)0.072 (3)0.033 (2)0.050 (2)
C100.101 (3)0.102 (3)0.089 (3)0.084 (3)0.042 (2)0.051 (2)
C110.118 (3)0.119 (3)0.070 (2)0.099 (3)0.052 (2)0.047 (2)
C120.098 (3)0.101 (3)0.0548 (19)0.080 (3)0.0409 (19)0.0431 (19)
C130.0342 (13)0.0342 (12)0.0410 (14)0.0177 (11)0.0110 (11)0.0129 (11)
C140.0469 (16)0.0484 (16)0.0402 (15)0.0203 (13)0.0123 (12)0.0156 (13)
C150.0598 (19)0.0504 (17)0.0392 (15)0.0216 (15)0.0042 (14)0.0078 (13)
C160.0461 (16)0.0383 (15)0.0587 (19)0.0159 (13)0.0002 (14)0.0095 (14)
C170.0370 (14)0.0340 (13)0.0624 (18)0.0183 (11)0.0154 (13)0.0206 (13)
C180.0380 (13)0.0356 (13)0.0446 (14)0.0193 (11)0.0154 (11)0.0166 (11)
N10.0385 (12)0.0345 (11)0.0334 (11)0.0122 (9)0.0148 (9)0.0112 (9)
O10.0403 (10)0.0344 (9)0.0417 (10)0.0139 (8)0.0168 (8)0.0131 (8)
O20.0459 (10)0.0438 (10)0.0400 (10)0.0288 (9)0.0195 (8)0.0183 (8)
O30.0603 (12)0.0545 (11)0.0421 (10)0.0409 (10)0.0266 (9)0.0268 (9)
P10.0364 (3)0.0322 (3)0.0355 (3)0.0181 (3)0.0160 (3)0.0158 (3)
Br10.0520 (2)0.04161 (19)0.0902 (3)0.01322 (15)0.02915 (18)0.02790 (17)
Geometric parameters (Å, º) top
C1—C61.366 (4)C11—C121.378 (5)
C1—C21.368 (4)C11—H110.93
C1—O21.419 (3)C12—H120.93
C2—C31.385 (5)C13—C141.388 (4)
C2—H20.93C13—C181.390 (4)
C3—C41.369 (6)C13—N11.415 (3)
C3—H30.93C14—C151.391 (4)
C4—C51.367 (6)C14—H140.93
C4—H40.93C15—C161.374 (5)
C5—C61.392 (5)C15—H150.93
C5—H50.93C16—C171.382 (4)
C6—H60.93C16—H160.93
C7—C81.364 (4)C17—C181.382 (4)
C7—C121.376 (4)C17—Br11.903 (3)
C7—O31.404 (3)C18—H180.93
C8—C91.374 (5)N1—P11.627 (2)
C8—H80.93N1—H10.874 (4)
C9—C101.363 (5)O1—P11.4626 (19)
C9—H90.93O2—P11.5769 (18)
C10—C111.362 (5)O3—P11.5772 (19)
C10—H100.93
C6—C1—C2122.0 (3)C7—C12—C11118.7 (3)
C6—C1—O2119.0 (3)C7—C12—H12120.6
C2—C1—O2118.9 (3)C11—C12—H12120.6
C1—C2—C3118.9 (3)C14—C13—C18119.8 (3)
C1—C2—H2120.5C14—C13—N1123.2 (2)
C3—C2—H2120.5C18—C13—N1117.0 (2)
C4—C3—C2119.9 (4)C13—C14—C15119.5 (3)
C4—C3—H3120.1C13—C14—H14120.2
C2—C3—H3120.1C15—C14—H14120.2
C5—C4—C3120.6 (3)C16—C15—C14121.4 (3)
C5—C4—H4119.7C16—C15—H15119.3
C3—C4—H4119.7C14—C15—H15119.3
C4—C5—C6120.1 (4)C15—C16—C17118.2 (3)
C4—C5—H5120C15—C16—H16120.9
C6—C5—H5120C17—C16—H16120.9
C1—C6—C5118.5 (3)C18—C17—C16121.9 (3)
C1—C6—H6120.8C18—C17—Br1118.5 (2)
C5—C6—H6120.8C16—C17—Br1119.5 (2)
C8—C7—C12120.9 (3)C17—C18—C13119.1 (3)
C8—C7—O3115.6 (2)C17—C18—H18120.4
C12—C7—O3123.5 (2)C13—C18—H18120.4
C7—C8—C9119.2 (3)C13—N1—P1129.42 (18)
C7—C8—H8120.4C13—N1—H1117 (2)
C9—C8—H8120.4P1—N1—H1112 (2)
C10—C9—C8120.7 (3)C1—O2—P1120.04 (16)
C10—C9—H9119.6C7—O3—P1124.83 (16)
C8—C9—H9119.6O1—P1—O2116.23 (11)
C11—C10—C9119.7 (3)O1—P1—O3115.60 (11)
C11—C10—H10120.2O2—P1—O395.39 (10)
C9—C10—H10120.2O1—P1—N1110.43 (11)
C10—C11—C12120.8 (3)O2—P1—N1108.56 (11)
C10—C11—H11119.6O3—P1—N1109.64 (12)
C12—C11—H11119.6
C6—C1—C2—C31.3 (5)C15—C16—C17—Br1178.3 (2)
O2—C1—C2—C3178.0 (3)C16—C17—C18—C130.4 (4)
C1—C2—C3—C40.3 (6)Br1—C17—C18—C13178.0 (2)
C2—C3—C4—C50.6 (6)C14—C13—C18—C170.2 (4)
C3—C4—C5—C60.6 (6)N1—C13—C18—C17178.7 (2)
C2—C1—C6—C51.3 (5)C14—C13—N1—P12.6 (4)
O2—C1—C6—C5178.0 (3)C18—C13—N1—P1178.6 (2)
C4—C5—C6—C10.4 (5)C6—C1—O2—P190.6 (3)
C12—C7—C8—C90.5 (5)C2—C1—O2—P192.6 (3)
O3—C7—C8—C9179.5 (3)C8—C7—O3—P1175.7 (2)
C7—C8—C9—C100.2 (6)C12—C7—O3—P15.2 (4)
C8—C9—C10—C110.8 (7)C1—O2—P1—O153.6 (2)
C9—C10—C11—C120.6 (8)C1—O2—P1—O3175.64 (19)
C8—C7—C12—C110.6 (6)C1—O2—P1—N171.5 (2)
O3—C7—C12—C11179.6 (4)C7—O3—P1—O156.5 (2)
C10—C11—C12—C70.1 (7)C7—O3—P1—O2179.0 (2)
C18—C13—C14—C150.4 (4)C7—O3—P1—N169.0 (2)
N1—C13—C14—C15178.4 (3)C13—N1—P1—O1177.8 (2)
C13—C14—C15—C160.1 (5)C13—N1—P1—O249.3 (3)
C14—C15—C16—C170.4 (5)C13—N1—P1—O353.7 (3)
C15—C16—C17—C180.7 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.87 (1)1.97 (1)2.837 (3)170 (3)
Symmetry code: (i) x+2, y+2, z+2.
(V) top
Crystal data top
C32H40N4O3P2F(000) = 1256
Mr = 590.62Dx = 1.293 Mg m3
Monoclinic, C2/cCu Kα radiation, λ = 1.54178 Å
Hall symbol: -C 2ycCell parameters from 3174 reflections
a = 19.050 (3) Åθ = 32.9–68.5°
b = 8.5308 (12) ŵ = 1.62 mm1
c = 18.821 (3) ÅT = 100 K
β = 97.341 (6)°Block, colorless
V = 3033.6 (8) Å30.20 × 0.10 × 0.10 mm
Z = 4
Data collection top
Bruker APEX-II CCD
diffractometer
2662 independent reflections
Radiation source: Cu rotating anode2640 reflections with I > 2σ(I)
Doubly curved mirrors monochromatorRint = 0.050
φ and ω scansθmax = 68.2°, θmin = 5.7°
Absorption correction: multi-scan
SADABS (Sheldrick, 2004)
h = 2115
Tmin = 0.738, Tmax = 0.855k = 1010
12338 measured reflectionsl = 2222
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0337P)2 + 3.5908P]
where P = (Fo2 + 2Fc2)/3
2662 reflections(Δ/σ)max < 0.001
188 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.33 e Å3
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
xyzUiso*/Ueq
P10.011654 (17)0.71027 (4)0.176053 (16)0.01157 (13)
O10.04695 (5)0.60378 (11)0.15054 (5)0.0157 (2)
O20.00000.79683 (14)0.25000.0134 (3)
N10.08733 (6)0.61642 (13)0.18719 (6)0.0142 (3)
N20.02439 (6)0.86483 (13)0.12811 (6)0.0149 (3)
C10.08950 (7)0.44947 (15)0.20642 (7)0.0157 (3)
H1B0.04040.40970.20430.019*
H1C0.11250.43790.25630.019*
C20.12904 (7)0.35087 (15)0.15763 (7)0.0149 (3)
C30.11774 (7)0.37084 (16)0.08350 (7)0.0177 (3)
H3A0.08770.45270.06340.021*
C40.15001 (8)0.27189 (17)0.03880 (8)0.0217 (3)
H4A0.14210.28660.01160.026*
C50.19373 (8)0.15171 (17)0.06763 (8)0.0235 (3)
H5A0.21540.08350.03700.028*
C60.20569 (8)0.13143 (17)0.14134 (8)0.0228 (3)
H6A0.23580.04950.16120.027*
C70.17354 (7)0.23109 (16)0.18622 (8)0.0183 (3)
H7A0.18210.21710.23670.022*
C80.15271 (7)0.70078 (17)0.21266 (8)0.0213 (3)
H8A0.19310.64590.19680.032*
H8B0.15860.70550.26510.032*
H8C0.15010.80740.19310.032*
C90.00910 (7)1.02782 (15)0.14534 (7)0.0154 (3)
H9A0.04021.09680.12090.018*
H9B0.02181.04300.19750.018*
C100.06688 (7)1.08148 (16)0.12518 (6)0.0144 (3)
C110.07994 (8)1.23960 (16)0.10948 (7)0.0174 (3)
H11A0.04131.31020.11020.021*
C120.14850 (8)1.29522 (17)0.09286 (8)0.0211 (3)
H12A0.15651.40320.08230.025*
C130.20529 (8)1.19326 (18)0.09159 (8)0.0211 (3)
H13A0.25231.23070.07980.025*
C140.19302 (8)1.03562 (17)0.10775 (7)0.0206 (3)
H14A0.23180.96560.10750.025*
C150.12434 (7)0.98018 (16)0.12429 (7)0.0175 (3)
H15A0.11650.87230.13510.021*
C160.03594 (8)0.83547 (17)0.05376 (7)0.0196 (3)
H16A0.07400.90340.04130.029*
H16B0.00770.85800.02180.029*
H16C0.04920.72550.04840.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0131 (2)0.00983 (19)0.01208 (19)0.00006 (12)0.00281 (13)0.00041 (11)
O10.0161 (5)0.0134 (5)0.0177 (5)0.0012 (4)0.0021 (4)0.0003 (4)
O20.0161 (7)0.0101 (6)0.0147 (6)0.0000.0044 (5)0.000
N10.0143 (6)0.0118 (5)0.0168 (5)0.0002 (4)0.0033 (4)0.0004 (4)
N20.0197 (6)0.0116 (6)0.0139 (5)0.0008 (4)0.0043 (4)0.0013 (4)
C10.0174 (7)0.0133 (7)0.0170 (6)0.0026 (5)0.0043 (5)0.0018 (5)
C20.0118 (6)0.0127 (6)0.0208 (7)0.0028 (5)0.0041 (5)0.0017 (5)
C30.0169 (7)0.0149 (7)0.0216 (7)0.0030 (5)0.0037 (5)0.0005 (5)
C40.0233 (8)0.0218 (7)0.0214 (7)0.0080 (6)0.0083 (6)0.0054 (6)
C50.0194 (8)0.0204 (7)0.0326 (8)0.0043 (6)0.0103 (6)0.0123 (6)
C60.0157 (7)0.0171 (7)0.0350 (8)0.0019 (5)0.0010 (6)0.0053 (6)
C70.0156 (7)0.0164 (7)0.0224 (7)0.0004 (5)0.0007 (5)0.0021 (5)
C80.0147 (7)0.0207 (7)0.0285 (8)0.0003 (5)0.0027 (6)0.0036 (6)
C90.0191 (7)0.0110 (6)0.0161 (6)0.0026 (5)0.0027 (5)0.0015 (5)
C100.0188 (7)0.0140 (6)0.0106 (6)0.0011 (5)0.0034 (5)0.0016 (5)
C110.0224 (7)0.0140 (6)0.0165 (6)0.0018 (6)0.0047 (5)0.0008 (5)
C120.0283 (8)0.0159 (7)0.0197 (7)0.0056 (6)0.0054 (6)0.0021 (5)
C130.0191 (7)0.0254 (8)0.0191 (7)0.0053 (6)0.0034 (5)0.0011 (6)
C140.0184 (7)0.0222 (7)0.0216 (7)0.0030 (6)0.0038 (5)0.0016 (6)
C150.0219 (7)0.0136 (7)0.0174 (6)0.0012 (5)0.0034 (5)0.0001 (5)
C160.0264 (8)0.0177 (7)0.0157 (7)0.0020 (6)0.0061 (5)0.0025 (5)
Geometric parameters (Å, º) top
P1—O11.4715 (10)C7—H7A0.9500
P1—O21.6157 (6)C8—H8A0.9800
P1—N21.6333 (11)C8—H8B0.9800
P1—N11.6389 (11)C8—H8C0.9800
O2—P1i1.6158 (6)C9—C101.5194 (19)
N1—C81.4650 (17)C9—H9A0.9900
N1—C11.4688 (17)C9—H9B0.9900
N2—C91.4655 (17)C10—C151.3931 (19)
N2—C161.4656 (17)C10—C111.3964 (19)
C1—C21.5149 (18)C11—C121.387 (2)
C1—H1B0.9900C11—H11A0.9500
C1—H1C0.9900C12—C131.386 (2)
C2—C71.3914 (19)C12—H12A0.9500
C2—C31.3947 (19)C13—C141.392 (2)
C3—C41.389 (2)C13—H13A0.9500
C3—H3A0.9500C14—C151.388 (2)
C4—C51.387 (2)C14—H14A0.9500
C4—H4A0.9500C15—H15A0.9500
C5—C61.388 (2)C16—H16A0.9800
C5—H5A0.9500C16—H16B0.9800
C6—C71.394 (2)C16—H16C0.9800
C6—H6A0.9500
O1—P1—O2112.41 (5)N1—C8—H8A109.5
O1—P1—N2118.57 (6)N1—C8—H8B109.5
O2—P1—N298.83 (6)H8A—C8—H8B109.5
O1—P1—N1111.01 (6)N1—C8—H8C109.5
O2—P1—N1109.18 (4)H8A—C8—H8C109.5
N2—P1—N1105.94 (6)H8B—C8—H8C109.5
P1—O2—P1i125.61 (8)N2—C9—C10116.14 (11)
C8—N1—C1113.57 (11)N2—C9—H9A108.3
C8—N1—P1119.94 (9)C10—C9—H9A108.3
C1—N1—P1120.11 (9)N2—C9—H9B108.3
C9—N2—C16115.58 (10)C10—C9—H9B108.3
C9—N2—P1126.58 (9)H9A—C9—H9B107.4
C16—N2—P1116.14 (9)C15—C10—C11118.57 (13)
N1—C1—C2112.92 (11)C15—C10—C9122.56 (12)
N1—C1—H1B109.0C11—C10—C9118.83 (12)
C2—C1—H1B109.0C12—C11—C10121.01 (13)
N1—C1—H1C109.0C12—C11—H11A119.5
C2—C1—H1C109.0C10—C11—H11A119.5
H1B—C1—H1C107.8C13—C12—C11119.97 (13)
C7—C2—C3119.02 (13)C13—C12—H12A120.0
C7—C2—C1119.93 (12)C11—C12—H12A120.0
C3—C2—C1120.89 (12)C12—C13—C14119.58 (14)
C4—C3—C2120.52 (13)C12—C13—H13A120.2
C4—C3—H3A119.7C14—C13—H13A120.2
C2—C3—H3A119.7C15—C14—C13120.35 (14)
C5—C4—C3120.15 (14)C15—C14—H14A119.8
C5—C4—H4A119.9C13—C14—H14A119.8
C3—C4—H4A119.9C14—C15—C10120.51 (13)
C4—C5—C6119.79 (13)C14—C15—H15A119.7
C4—C5—H5A120.1C10—C15—H15A119.7
C6—C5—H5A120.1N2—C16—H16A109.5
C5—C6—C7120.07 (14)N2—C16—H16B109.5
C5—C6—H6A120.0H16A—C16—H16B109.5
C7—C6—H6A120.0N2—C16—H16C109.5
C2—C7—C6120.44 (14)H16A—C16—H16C109.5
C2—C7—H7A119.8H16B—C16—H16C109.5
C6—C7—H7A119.8
O1—P1—O2—P1i57.39 (4)C1—C2—C3—C4174.97 (12)
N2—P1—O2—P1i176.63 (4)C2—C3—C4—C50.2 (2)
N1—P1—O2—P1i66.25 (5)C3—C4—C5—C60.6 (2)
O1—P1—N1—C8179.80 (9)C4—C5—C6—C70.3 (2)
O2—P1—N1—C855.33 (11)C3—C2—C7—C60.7 (2)
N2—P1—N1—C850.24 (11)C1—C2—C7—C6174.75 (12)
O1—P1—N1—C129.65 (11)C5—C6—C7—C20.3 (2)
O2—P1—N1—C194.82 (10)C16—N2—C9—C1081.28 (14)
N2—P1—N1—C1159.61 (9)P1—N2—C9—C1083.20 (14)
O1—P1—N2—C9107.25 (11)N2—C9—C10—C1530.75 (17)
O2—P1—N2—C914.35 (11)N2—C9—C10—C11151.68 (12)
N1—P1—N2—C9127.31 (11)C15—C10—C11—C120.41 (19)
O1—P1—N2—C1657.16 (12)C9—C10—C11—C12178.07 (12)
O2—P1—N2—C16178.75 (9)C10—C11—C12—C130.1 (2)
N1—P1—N2—C1668.29 (11)C11—C12—C13—C140.6 (2)
C8—N1—C1—C279.60 (14)C12—C13—C14—C150.7 (2)
P1—N1—C1—C2128.47 (10)C13—C14—C15—C100.2 (2)
N1—C1—C2—C7139.80 (12)C11—C10—C15—C140.33 (19)
N1—C1—C2—C344.81 (17)C9—C10—C15—C14177.91 (12)
C7—C2—C3—C40.5 (2)
Symmetry code: (i) x, y, z+1/2.
(VI) top
Crystal data top
C28H32N4O3P2Dx = 1.313 Mg m3
Mr = 534.52Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PccnCell parameters from 9950 reflections
a = 13.4363 (9) Åθ = 2.8–27.2°
b = 20.3532 (13) ŵ = 0.20 mm1
c = 9.8851 (6) ÅT = 90 K
V = 2703.3 (3) Å3BLOCK, colourless
Z = 40.28 × 0.10 × 0.10 mm
F(000) = 1128
Data collection top
Bruker APEX-II CCD
diffractometer
3021 independent reflections
Radiation source: fine-focus sealed tube2613 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
φ and ω scansθmax = 27.2°, θmin = 2.8°
Absorption correction: multi-scan
SADABS (Sheldrick, 2004)
h = 1717
Tmin = 0.947, Tmax = 0.981k = 2526
21713 measured reflectionsl = 1212
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0464P)2 + 2.0756P]
where P = (Fo2 + 2Fc2)/3
3021 reflections(Δ/σ)max = 0.017
176 parametersΔρmax = 0.40 e Å3
2 restraintsΔρmin = 0.36 e Å3
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
xyzUiso*/Ueq
P10.66141 (3)0.711940 (19)0.54774 (4)0.01271 (12)
O10.75000.75000.47179 (14)0.0136 (3)
O20.62320 (8)0.74693 (6)0.66640 (10)0.0189 (2)
N10.70297 (10)0.63958 (7)0.59323 (13)0.0174 (3)
H1N0.7206 (14)0.6402 (9)0.6772 (11)0.021*
N20.58768 (9)0.70329 (6)0.41932 (12)0.0138 (3)
H2N0.6069 (13)0.7211 (8)0.3454 (12)0.017*
C10.76183 (11)0.60001 (7)0.50390 (16)0.0168 (3)
C20.86464 (12)0.59971 (8)0.51515 (18)0.0220 (3)
H2A0.89640.62530.58300.026*
C30.92079 (13)0.56202 (8)0.42709 (19)0.0250 (4)
H3A0.99120.56160.43640.030*
C40.87690 (13)0.52478 (8)0.32545 (17)0.0219 (3)
C50.77378 (12)0.52519 (8)0.31648 (17)0.0209 (3)
H5A0.74200.49970.24860.025*
C60.71618 (12)0.56224 (8)0.40504 (17)0.0196 (3)
H6A0.64570.56170.39780.024*
C70.93964 (15)0.48668 (9)0.2267 (2)0.0313 (4)
H7A0.91220.44240.21600.047*
H7B1.00800.48370.26090.047*
H7C0.93960.50910.13900.047*
C80.48717 (11)0.68338 (7)0.42887 (15)0.0144 (3)
C90.45075 (12)0.64930 (8)0.54057 (16)0.0186 (3)
H9A0.49390.63820.61310.022*
C100.35111 (12)0.63166 (8)0.54528 (17)0.0217 (3)
H10A0.32700.60840.62180.026*
C110.28565 (12)0.64707 (8)0.44133 (17)0.0215 (3)
C120.32386 (12)0.68041 (8)0.32971 (17)0.0205 (3)
H12A0.28080.69110.25670.025*
C130.42303 (11)0.69835 (7)0.32283 (16)0.0171 (3)
H13A0.44740.72090.24550.021*
C140.17736 (13)0.62836 (10)0.44902 (19)0.0302 (4)
H14A0.17140.58040.45430.045*
H14B0.14280.64420.36810.045*
H14C0.14740.64820.52960.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.01118 (19)0.0169 (2)0.0101 (2)0.00020 (13)0.00030 (13)0.00116 (13)
O10.0128 (7)0.0181 (7)0.0099 (7)0.0022 (6)0.0000.000
O20.0173 (5)0.0271 (6)0.0124 (5)0.0008 (4)0.0013 (4)0.0021 (4)
N10.0167 (6)0.0215 (7)0.0141 (6)0.0024 (5)0.0002 (5)0.0044 (5)
N20.0118 (6)0.0190 (6)0.0105 (6)0.0024 (5)0.0000 (5)0.0027 (5)
C10.0162 (7)0.0150 (7)0.0192 (7)0.0010 (5)0.0005 (6)0.0060 (6)
C20.0169 (8)0.0193 (8)0.0300 (9)0.0005 (6)0.0032 (7)0.0018 (7)
C30.0157 (8)0.0198 (8)0.0395 (10)0.0007 (6)0.0000 (7)0.0018 (7)
C40.0245 (8)0.0137 (7)0.0276 (9)0.0015 (6)0.0041 (7)0.0039 (6)
C50.0253 (9)0.0154 (7)0.0221 (8)0.0019 (6)0.0027 (6)0.0030 (6)
C60.0164 (7)0.0179 (7)0.0246 (8)0.0018 (6)0.0018 (6)0.0051 (6)
C70.0343 (10)0.0211 (8)0.0386 (11)0.0042 (7)0.0078 (8)0.0032 (8)
C80.0121 (7)0.0149 (7)0.0161 (7)0.0006 (5)0.0007 (5)0.0015 (5)
C90.0163 (7)0.0228 (8)0.0167 (7)0.0019 (6)0.0005 (6)0.0027 (6)
C100.0198 (8)0.0260 (8)0.0194 (8)0.0046 (6)0.0044 (6)0.0042 (6)
C110.0143 (7)0.0250 (8)0.0253 (8)0.0032 (6)0.0019 (6)0.0007 (7)
C120.0153 (7)0.0241 (8)0.0220 (8)0.0003 (6)0.0036 (6)0.0001 (6)
C130.0166 (7)0.0179 (7)0.0169 (7)0.0011 (6)0.0005 (6)0.0019 (6)
C140.0164 (8)0.0436 (11)0.0307 (10)0.0079 (7)0.0009 (7)0.0039 (8)
Geometric parameters (Å, º) top
P1—O21.4651 (11)C6—H6A0.9500
P1—O11.6064 (7)C7—H7A0.9800
P1—N21.6199 (13)C7—H7B0.9800
P1—N11.6380 (14)C7—H7C0.9800
O1—P1i1.6064 (7)C8—C131.391 (2)
N1—C11.433 (2)C8—C91.393 (2)
N1—H1N0.863 (9)C9—C101.387 (2)
N2—C81.4132 (19)C9—H9A0.9500
N2—H2N0.856 (9)C10—C111.388 (2)
C1—C21.386 (2)C10—H10A0.9500
C1—C61.386 (2)C11—C121.393 (2)
C2—C31.384 (2)C11—C141.506 (2)
C2—H2A0.9500C12—C131.383 (2)
C3—C41.390 (2)C12—H12A0.9500
C3—H3A0.9500C13—H13A0.9500
C4—C51.388 (2)C14—H14A0.9800
C4—C71.505 (2)C14—H14B0.9800
C5—C61.391 (2)C14—H14C0.9800
C5—H5A0.9500
O2—P1—O1113.54 (6)C4—C7—H7A109.5
O2—P1—N2117.77 (7)C4—C7—H7B109.5
O1—P1—N298.00 (6)H7A—C7—H7B109.5
O2—P1—N1109.68 (7)C4—C7—H7C109.5
O1—P1—N1108.02 (5)H7A—C7—H7C109.5
N2—P1—N1109.02 (7)H7B—C7—H7C109.5
P1i—O1—P1124.27 (9)C13—C8—C9119.27 (14)
C1—N1—P1121.62 (10)C13—C8—N2118.62 (13)
C1—N1—H1N116.7 (13)C9—C8—N2122.11 (14)
P1—N1—H1N110.2 (13)C10—C9—C8119.65 (14)
C8—N2—P1124.28 (10)C10—C9—H9A120.2
C8—N2—H2N117.8 (13)C8—C9—H9A120.2
P1—N2—H2N116.0 (13)C9—C10—C11121.88 (15)
C2—C1—C6119.68 (15)C9—C10—H10A119.1
C2—C1—N1120.20 (15)C11—C10—H10A119.1
C6—C1—N1120.11 (14)C10—C11—C12117.56 (14)
C3—C2—C1119.69 (16)C10—C11—C14121.17 (15)
C3—C2—H2A120.2C12—C11—C14121.27 (15)
C1—C2—H2A120.2C13—C12—C11121.50 (15)
C2—C3—C4121.71 (16)C13—C12—H12A119.3
C2—C3—H3A119.1C11—C12—H12A119.3
C4—C3—H3A119.1C12—C13—C8120.13 (14)
C5—C4—C3117.80 (15)C12—C13—H13A119.9
C5—C4—C7121.38 (16)C8—C13—H13A119.9
C3—C4—C7120.80 (16)C11—C14—H14A109.5
C4—C5—C6121.22 (15)C11—C14—H14B109.5
C4—C5—H5A119.4H14A—C14—H14B109.5
C6—C5—H5A119.4C11—C14—H14C109.5
C1—C6—C5119.88 (15)H14A—C14—H14C109.5
C1—C6—H6A120.1H14B—C14—H14C109.5
C5—C6—H6A120.1
O2—P1—O1—P1i40.76 (5)C7—C4—C5—C6177.78 (15)
N2—P1—O1—P1i165.82 (5)C2—C1—C6—C51.0 (2)
N1—P1—O1—P1i81.11 (5)N1—C1—C6—C5178.42 (14)
O2—P1—N1—C1167.66 (12)C4—C5—C6—C10.5 (2)
O1—P1—N1—C143.43 (14)P1—N2—C8—C13158.75 (12)
N2—P1—N1—C162.05 (14)P1—N2—C8—C921.4 (2)
O2—P1—N2—C845.62 (14)C13—C8—C9—C100.9 (2)
O1—P1—N2—C8167.62 (11)N2—C8—C9—C10179.22 (15)
N1—P1—N2—C880.11 (13)C8—C9—C10—C110.1 (3)
P1—N1—C1—C297.96 (16)C9—C10—C11—C120.9 (3)
P1—N1—C1—C681.50 (17)C9—C10—C11—C14179.13 (17)
C6—C1—C2—C30.4 (2)C10—C11—C12—C130.8 (2)
N1—C1—C2—C3179.09 (15)C14—C11—C12—C13179.27 (16)
C1—C2—C3—C40.9 (3)C11—C12—C13—C80.2 (2)
C2—C3—C4—C51.5 (2)C9—C8—C13—C121.0 (2)
C2—C3—C4—C7177.10 (16)N2—C8—C13—C12179.08 (14)
C3—C4—C5—C60.8 (2)
Symmetry code: (i) x+3/2, y+3/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O2ii0.86 (1)1.90 (1)2.7395 (16)168 (2)
C13—H13A···O2ii0.952.573.2963 (19)133
Symmetry code: (ii) x, y+3/2, z1/2.
 

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