Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113022981/fg3306sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113022981/fg3306Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113022981/fg3306IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113022981/fg3306IIIsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113022981/fg3306IVsup5.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113022981/fg3306Isup6.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113022981/fg3306IIsup7.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113022981/fg3306IIIsup8.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113022981/fg3306IVsup9.cml |
CCDC references: 969460; 969461; 969462; 969463
α-Aminophosphonates are structural analogues of natural amino acids. They have been the subject of considerable attention due to their potential biological activities. They may be applied as enzyme inhibitors (Maier & Spörri, 1991), antibacterial agents (Atherton et al., 1986), antitumour agents (Lavielle et al., 1991) or antiviral agents (Huang & Chen, 2000; Xu et al., 2006). α-Aminophosphonates can be synthesized via the Kabachnik–Fields reaction (Cherkasov & Galkin, 1998) by the coupling of a carbonyl, an amine and a dialkylphosphite unit. We report here the syntheses and crystal structures of four diethyl arylamino(4-ethynylphenyl)methylphosphonate derivatives, namely diethyl [(4-bromoanilino)(4-ethynylphenyl)methyl]phosphonate, (I), diethyl ((4-chloro-2-methylanilino){4-[2-(trimethylsilyl)ethynyl]phenyl}methyl)phosphonate, (II), diethyl ((4-fluoroanilino){4-[2-(trimethylsilyl)ethynyl]phenyl}methyl)phosphonate, (III), and diethyl [(4-ethynylphenyl)(naphthalen-2-ylamino)methyl]phosphonate, (IV).
Compounds (I)–(IV) were prepared via a three-component reaction of an aldehyde, an amine and diethyl phosphite, as described by Wu et al. (2006). Thus, 4-(trimethylsilylethynyl)benzaldehyde (1 mmol) was reacted at room temperature with 4-bromoaniline (1.2 mmol) and diethyl phosphite (1.2 mmol) in acetonitrile (2.5 ml) using molecular iodine (0.2 mmol) as catalyst. Next, the trimethylsilyl group was removed by reacting the product with tetrabutylammonium fluoride (1 equivalent) in tetrahydrofurane (2.5 ml). Compound (I) was obtained in a yield of 83%. The crude product was purified by chromatography through a column filled with silica gel, using ethyl acetate/n-hexane (7:3 v/v) as solvent. Recrystallization from ethyl acetate resulted in pale-brown blocks of (I).
4-(Trimethylsilylethynyl)benzaldehyde (1 mmol) was reacted at room temperature with 4-chloro-2-methylaniline (1.2 mmol) and diethyl phosphite (1.2 mmol) in acetonitrile (2.5 ml) using molecular iodine (0.2 mmol) as catalyst, resulting in (II) in a yield of 87%. The solvent was removed and the residue purified through a silica-gel column using ethyl acetate/n-hexane (7:3 v/v) as solvent. Recrystallization from ethyl acetate/n-hexane (7:3 v/v) resulted in pale-brown blocks of (II).
4-(Trimethylsilylethynyl)benzaldehyde (1 mmol) was reacted at room temperature with 4-fluoroaniline (1.2 mmol) and diethylphosphite (1.2 mmol) in acetonitrile (2.5 ml) using molecular iodine (0.2 mmol) as catalyst, resulting in (III) in a yield of 77%. The solvent was removed and the residue purified through a silica-gel column using ethyl acetate/n-hexane (7:3 v/v) as solvent. Recrystallization from ethyl acetate/n-hexane (7:3 v/v) resulted in pale-brown blocks of (III).
4-(Trimethylsilylethynyl)benzaldehyde (1 mmol) was reacted at room temperature with β-naphthylamine (1.2 mmol) and diethylphosphite (1.2 mmol) in acetonitrile (2.5 ml) using molecular iodine (0.2 mmol) as catalyst. Next, the trimethylsilyl group was removed by reacting the product with tetrabutylammonium fluoride (1 equivalent) in tetrahydrofuran (2.5 ml). Compound (IV) was obtained in a yield of 93%. The crude product was purified by chromatography through a column filled with silica gel using dichloromethane as solvent. Recrystallization from ethyl acetate/n-hexane (7:3 v/v) resulted in pale-brown blocks of (IV).
Crystal data, data collection and structure refinement details are summarized in Table 1. C-bound H atoms were positioned geometrically and treated as riding, with C—H = 0.95–1.00 Å, and with Uiso(H) = 1.5Ueq(C) for methyl H atoms or 1.2Ueq(C) for other H atoms. N-bound H atoms were located from difference Fourier syntheses; their coordinates and isotropic displacement parameters were refined. Some ethyl groups in (I) and (II) were found to be disordered over two orientations and were refined with split atoms. The occupancy factors refined to 0.881 (9) for C17, 0.877 (7) for C18 and C19, 0.119 (9) for C17', 0.123 (7) for C18' and C19' of (I), and 0.516 (11) for C18 and C19 and 0.484 (11) for C18' and C19' of (II). The crystal structure of (II) was refined in the nonstandard space group I2/a rather than in C2/c, to avoid a large monoclinic angle of β = 130.698 (1)°.
The conformation of the anilinobenzyl fragment of (I) (Fig. 1) is very similar to that observed in the crystal structure of unsubstituted diethyl anilinobenzylphosphonate (Rużić-Toroš et al., 1978). The P1—C1 bond has a staggered conformation, with the C1—H bond in a trans position with respect to the P═O double bond. The two benzene rings are almost perpendicular [angle between planes = 87.34 (7)°]. The ethynyl group shows a small deviation from the plane of the C2–C7 benzene ring [atoms C8 and C9 deviate by 0.037 (3) and 0.079 (4) Å, respectively, from the benzene plane]. The N atom shows a small deviation from planarity; the sum of the three valence angles about the N atom is 345 (1)°. The molecules are connected by intermolecular N—H···O═P hydrogen bonds to form centrosymmetric dimers (Fig. 2, Table 2). The dimers are also stabilized by two intermolecular C—H···O═P contacts, with H···O distances of 2.55 and 2.59 Å. Neighbouring dimers are connected by a weak intermolecular Cethynyl—H···N contact, an additional C—H···O contact, two very weak C—H···Br contacts and a Cmethyl—H···πbenzene contact.
The conformation of the anilinobenzyl fragment of (II) (Fig. 3) is very similar to that observed for (I). The angle between the planes of the benzene rings is 82.49 (14)°. The N atom again shows a small deviation from planarity; the sum of the three valence angles about the N atom is 346 (3)°. The N—H bond is not involved in hydrogen bonding. The crystal packing of (II) is shown in Fig. 4. The molecules are connected by intermolecular C—H···O═P contacts, with H···O distances of 2.49 and 2.60 Å, to form centrosymmetric dimers (Table 3). The shorter of these contacts involves the methyl group attached to the aniline group. The presence of this methyl group near the N—H bond may prevent the amino group from being involved in the hydrogen-bonding system. A similar situation is found in the crystal structure of diethyl [(2-chlorophenylamino)(2-hydroxyphenyl)methyl]phosphonate (Wang et al., 2012). There, a Cl substituent is positioned next to the N—H bond and again the amino group is not involved in intermolecular hydrogen bonding. The dimers of (II) are connected by an additional C—H···O contact, with an H···O distance of 2.54 Å.
The molecular structure of (III) (Fig. 5) is rather similar to the structures of (I) and (II). The sum of the three valence angles about the N atom is 344 (2)°. The angle between the benzene planes is 87.96 (8)°. The crystal packing of (III) is shown in Fig. 6. The molecules are arranged to form centrosymmetric dimers connected by two symmetry-related N—H···O═P hydrogen bonds (Table 4). The dimers are also stabilized by two C—H···O═ P contacts, with H···O distances of 2.44 and 2.71 Å. Neigbouring dimers are connected by two very weak intermolecular Cmethyl—H···πbenzene interactions and two weak intermolecular Cbenzene—H···F contacts, with H···F distances of 2.67 and 2.76 Å, respectively.
Crystals of (IV) undergo a phase transition on cooling from room temperature to 180 K, accompanied by a doubling of the unit-cell volume. The cell constants at room temperature are a = 10.0601 (15), b = 11.452 (2) and c = 11.506 (3) Å, and α = 111.314 (14), β = 114.179 (12) and γ = 96.888 (11)°. The low-temperature unit cell is related to the room-temperature unit cell by the transformations alt = -brt, blt = art + crt and clt = -art + crt. Consequently, the asymmetric unit of (IV) at 180 K contains two independent molecules (A and B; Fig. 7), which are approximately related by pseudo-translation [0 1/2 1/2]. The conformations of molecules A and B differ mainly in the relative orientations of the ethoxy groups attached to the P atoms. The angle between the naphthyl and benzene planes is 86.05 (9)° for molecule A and 85.92 (8)° for molecule B. The ethynyl group shows a considerable deviation from the plane of the benzene ring for molecule B [atoms C31 and C32 deviate by 0.175 (5) and 0.391 (6) Å, respectively, from the benzene plane]. A smaller deviation is observed for the ethynyl group of molecule A [atoms C8 And C9 deviate by 0.061 (5) and 0.141 (6) Å, respectively, from the benzene plane]. The sum of the three valence angles about the N atom is 351 (2)° for N1 and 349 (2)° for N2. The crystal packing of (IV) is shown in Fig. 8. In the crystal structure, molecules are connected to form pseudocentrosymmetric dimers. Each dimer consists of a molecule A and a molecule B, which are connected by two N—H···O═P hydrogen bonds, and by two C—H···O═P contacts with H···O distances of 2.48 and 2.56 Å, respectively (Table 5). Neigbouring dimers are connected by an intermolecular Cethynyl—H···O contact with an H···O distance of 2.44 Å. The latter contact is rather short and may be responsible for the nonplanarity of the ethynylphenyl group of molecule B. There are also a number of weak intermolecular C—H···πbenzene and C—H···πnaphthyl interactions and an additional C—H···O contact, with an H···O distance of 2.63 Å (Table 5).
The conformation of the anilinobenzyl group is very similar in all four compounds. Selected torsion angles in (I)–(IV) are reported in Table 6 and compared with the corresponding torsion angles in other anilino–phenylmethyl phosphonate structures with no substituents at the ortho positions of the benzene rings. The six-membered ring of the anilino group is almost coplanar with the amino group in all compounds. The P—C bond has an approximately staggered conformation in all structures, with the C1—N1 and C1—C2 bonds in gauche positions and the C1—H bond in a trans position with respect to the P═O double bond. For the C2—C1—N1—C10 torsion angle, two possible orientations are found: in 17 structures the torsion angle has a value of -69 (5)°, while in four structures values between -114 and -147° are found. The intramolecular N—H···O═P contact is shorter in the former case (H···O distances 2.64–2.91 Å), which may therefore correspond to the preferred conformation. For the C3—C2—C1—N1 torsion angle, a value near -47 (10)° is found in all structures. This corresponds to the conformation where the benzyl plane is almost parallel to the C1—H bond. In the crystal structures, the anilinobenzylphosphonate units of all molecules listed in Table 6 are connected to form centrosymmetric or pseudo-centrosymmetric dimers. In each dimer, except in (II), the molecules are connected by two N—H···O═P hydrogen bonds. In (II), where the amino N—H bond is shielded by a methyl substituent in the ortho-position of the aniline ring, no N—H···O hydrogen bond is found. Here, Cmethyl—H···O═P hydrogen bonds connect the molecules to form centrosymmetric dimers.
For all compounds, data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
C19H21BrNO3P | F(000) = 864 |
Mr = 422.25 | Dx = 1.438 Mg m−3 |
Monoclinic, P21/n | Melting point: 416(1) K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 10.9339 (7) Å | Cell parameters from 7719 reflections |
b = 16.5179 (11) Å | θ = 3–27° |
c = 11.1325 (7) Å | µ = 2.21 mm−1 |
β = 104.114 (1)° | T = 186 K |
V = 1949.9 (2) Å3 | Block, pale brown |
Z = 4 | 0.60 × 0.60 × 0.50 mm |
Siemens SMART 1K CCD area-detector diffractometer | 4762 independent reflections |
Radiation source: normal-focus sealed tube | 4104 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ω scans | θmax = 28.2°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | h = −14→14 |
Tmin = 0.284, Tmax = 0.332 | k = −21→21 |
22735 measured reflections | l = −14→14 |
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)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.079 | w = 1/[σ2(Fo2) + (0.025P)2 + 1.3P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.001 |
4762 reflections | Δρmax = 0.47 e Å−3 |
245 parameters | Δρmin = −0.43 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0039 (4) |
C19H21BrNO3P | V = 1949.9 (2) Å3 |
Mr = 422.25 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.9339 (7) Å | µ = 2.21 mm−1 |
b = 16.5179 (11) Å | T = 186 K |
c = 11.1325 (7) Å | 0.60 × 0.60 × 0.50 mm |
β = 104.114 (1)° |
Siemens SMART 1K CCD area-detector diffractometer | 4762 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | 4104 reflections with I > 2σ(I) |
Tmin = 0.284, Tmax = 0.332 | Rint = 0.031 |
22735 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.079 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | Δρmax = 0.47 e Å−3 |
4762 reflections | Δρmin = −0.43 e Å−3 |
245 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Br1 | 0.44620 (2) | 0.162990 (14) | 0.40970 (2) | 0.04550 (9) | |
P1 | 0.84365 (4) | 0.62113 (3) | 0.49540 (4) | 0.02480 (12) | |
O1 | 0.97550 (12) | 0.60700 (9) | 0.49191 (14) | 0.0343 (3) | |
O2 | 0.77945 (13) | 0.69708 (9) | 0.42188 (14) | 0.0343 (3) | |
O3 | 0.82091 (13) | 0.63275 (9) | 0.62817 (13) | 0.0339 (3) | |
N1 | 0.77465 (15) | 0.46582 (10) | 0.50665 (15) | 0.0258 (3) | |
H1B | 0.849 (2) | 0.4551 (14) | 0.517 (2) | 0.037 (6)* | |
C1 | 0.73722 (16) | 0.53871 (11) | 0.43243 (17) | 0.0247 (4) | |
H1A | 0.6508 | 0.5542 | 0.4395 | 0.030* | |
C2 | 0.73341 (17) | 0.53028 (11) | 0.29485 (17) | 0.0254 (4) | |
C3 | 0.83644 (19) | 0.49747 (13) | 0.25893 (18) | 0.0338 (5) | |
H3A | 0.9071 | 0.4786 | 0.3202 | 0.041* | |
C4 | 0.8369 (2) | 0.49211 (14) | 0.13498 (19) | 0.0368 (5) | |
H4A | 0.9083 | 0.4702 | 0.1120 | 0.044* | |
C5 | 0.7334 (2) | 0.51861 (12) | 0.04342 (18) | 0.0306 (4) | |
C6 | 0.6311 (2) | 0.55212 (12) | 0.07949 (19) | 0.0346 (5) | |
H6A | 0.5606 | 0.5714 | 0.0184 | 0.041* | |
C7 | 0.63142 (18) | 0.55764 (12) | 0.20376 (18) | 0.0306 (4) | |
H7A | 0.5608 | 0.5805 | 0.2269 | 0.037* | |
C8 | 0.7344 (2) | 0.51049 (13) | −0.0856 (2) | 0.0376 (5) | |
C9 | 0.7375 (2) | 0.50198 (15) | −0.1907 (2) | 0.0454 (6) | |
H9A | 0.7399 | 0.4952 | −0.2748 | 0.055* | |
C10 | 0.69665 (17) | 0.39730 (11) | 0.48211 (16) | 0.0245 (4) | |
C11 | 0.56698 (18) | 0.40216 (12) | 0.42991 (19) | 0.0301 (4) | |
H11A | 0.5291 | 0.4535 | 0.4075 | 0.036* | |
C12 | 0.49261 (19) | 0.33260 (13) | 0.4104 (2) | 0.0334 (4) | |
H12A | 0.4044 | 0.3366 | 0.3757 | 0.040* | |
C13 | 0.54771 (19) | 0.25799 (12) | 0.44163 (19) | 0.0319 (4) | |
C14 | 0.6760 (2) | 0.25156 (13) | 0.4943 (2) | 0.0336 (4) | |
H14A | 0.7134 | 0.2000 | 0.5162 | 0.040* | |
C15 | 0.74927 (19) | 0.32088 (12) | 0.51483 (19) | 0.0305 (4) | |
H15A | 0.8370 | 0.3165 | 0.5519 | 0.037* | |
C16 | 0.8259 (3) | 0.73571 (15) | 0.3239 (2) | 0.0473 (6) | 0.877 (11) |
H16A | 0.7540 | 0.7491 | 0.2535 | 0.057* | 0.877 (11) |
H16B | 0.8821 | 0.6979 | 0.2938 | 0.057* | 0.877 (11) |
C16' | 0.8259 (3) | 0.73571 (15) | 0.3239 (2) | 0.0473 (6) | 0.123 (11) |
H16C | 0.9149 | 0.7207 | 0.3304 | 0.057* | 0.123 (11) |
H16D | 0.7747 | 0.7191 | 0.2415 | 0.057* | 0.123 (11) |
C17 | 0.8959 (6) | 0.81067 (19) | 0.3710 (3) | 0.0601 (15) | 0.877 (11) |
H17A | 0.9267 | 0.8361 | 0.3045 | 0.090* | 0.877 (11) |
H17B | 0.9676 | 0.7972 | 0.4400 | 0.090* | 0.877 (11) |
H17C | 0.8398 | 0.8483 | 0.3997 | 0.090* | 0.877 (11) |
C17' | 0.815 (3) | 0.8204 (11) | 0.3414 (19) | 0.037 (6)* | 0.123 (11) |
H17D | 0.7265 | 0.8368 | 0.3106 | 0.056* | 0.123 (11) |
H17E | 0.8671 | 0.8496 | 0.2957 | 0.056* | 0.123 (11) |
H17F | 0.8430 | 0.8333 | 0.4297 | 0.056* | 0.123 (11) |
C18 | 0.9149 (3) | 0.66885 (18) | 0.7308 (2) | 0.0408 (8) | 0.877 (7) |
H18A | 0.9987 | 0.6455 | 0.7321 | 0.049* | 0.877 (7) |
H18B | 0.8941 | 0.6543 | 0.8098 | 0.049* | 0.877 (7) |
C18' | 0.861 (2) | 0.7080 (13) | 0.696 (2) | 0.042 (6)* | 0.123 (7) |
H18C | 0.8275 | 0.7546 | 0.6420 | 0.050* | 0.123 (7) |
H18D | 0.8233 | 0.7103 | 0.7688 | 0.050* | 0.123 (7) |
C19 | 0.9224 (4) | 0.7579 (2) | 0.7227 (3) | 0.0581 (11) | 0.877 (7) |
H19A | 0.9867 | 0.7784 | 0.7936 | 0.087* | 0.877 (7) |
H19B | 0.8404 | 0.7816 | 0.7235 | 0.087* | 0.877 (7) |
H19C | 0.9450 | 0.7729 | 0.6457 | 0.087* | 0.877 (7) |
C19' | 0.996 (2) | 0.7154 (13) | 0.7383 (19) | 0.044 (6)* | 0.123 (7) |
H19D | 1.0172 | 0.7666 | 0.7832 | 0.066* | 0.123 (7) |
H19E | 1.0335 | 0.7145 | 0.6668 | 0.066* | 0.123 (7) |
H19F | 1.0294 | 0.6701 | 0.7935 | 0.066* | 0.123 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.04488 (14) | 0.03430 (13) | 0.05704 (17) | −0.01325 (10) | 0.01189 (11) | −0.00322 (10) |
P1 | 0.0230 (2) | 0.0267 (2) | 0.0258 (2) | −0.00257 (18) | 0.00832 (18) | −0.00322 (19) |
O1 | 0.0244 (7) | 0.0365 (8) | 0.0436 (8) | −0.0035 (6) | 0.0113 (6) | −0.0050 (6) |
O2 | 0.0369 (8) | 0.0291 (7) | 0.0380 (8) | 0.0010 (6) | 0.0114 (6) | 0.0006 (6) |
O3 | 0.0349 (7) | 0.0402 (8) | 0.0280 (7) | −0.0097 (6) | 0.0105 (6) | −0.0086 (6) |
N1 | 0.0214 (8) | 0.0287 (8) | 0.0276 (8) | −0.0013 (6) | 0.0064 (6) | −0.0011 (6) |
C1 | 0.0213 (8) | 0.0268 (9) | 0.0267 (9) | −0.0009 (7) | 0.0073 (7) | −0.0036 (7) |
C2 | 0.0265 (9) | 0.0247 (9) | 0.0248 (9) | −0.0021 (7) | 0.0056 (7) | −0.0022 (7) |
C3 | 0.0289 (10) | 0.0454 (12) | 0.0257 (10) | 0.0097 (9) | 0.0041 (8) | −0.0014 (9) |
C4 | 0.0373 (11) | 0.0449 (12) | 0.0296 (11) | 0.0086 (9) | 0.0107 (9) | −0.0001 (9) |
C5 | 0.0399 (11) | 0.0253 (10) | 0.0251 (10) | −0.0028 (8) | 0.0048 (8) | 0.0015 (8) |
C6 | 0.0344 (11) | 0.0321 (11) | 0.0318 (11) | 0.0032 (8) | −0.0023 (8) | 0.0040 (8) |
C7 | 0.0275 (9) | 0.0293 (10) | 0.0336 (11) | 0.0035 (8) | 0.0051 (8) | −0.0018 (8) |
C8 | 0.0464 (13) | 0.0325 (11) | 0.0317 (11) | −0.0003 (9) | 0.0052 (9) | 0.0049 (9) |
C9 | 0.0584 (15) | 0.0486 (14) | 0.0286 (12) | 0.0021 (11) | 0.0092 (10) | 0.0044 (10) |
C10 | 0.0253 (9) | 0.0301 (10) | 0.0213 (9) | −0.0028 (7) | 0.0114 (7) | −0.0037 (7) |
C11 | 0.0271 (9) | 0.0286 (10) | 0.0359 (11) | 0.0014 (7) | 0.0103 (8) | −0.0033 (8) |
C12 | 0.0242 (9) | 0.0385 (11) | 0.0385 (11) | −0.0036 (8) | 0.0097 (8) | −0.0060 (9) |
C13 | 0.0325 (10) | 0.0300 (10) | 0.0365 (11) | −0.0093 (8) | 0.0148 (9) | −0.0049 (8) |
C14 | 0.0365 (11) | 0.0302 (10) | 0.0364 (11) | 0.0007 (8) | 0.0137 (9) | 0.0035 (8) |
C15 | 0.0250 (9) | 0.0357 (11) | 0.0315 (10) | 0.0011 (8) | 0.0083 (8) | 0.0029 (8) |
C16 | 0.0695 (17) | 0.0417 (13) | 0.0329 (12) | 0.0004 (12) | 0.0166 (11) | 0.0068 (10) |
C16' | 0.0695 (17) | 0.0417 (13) | 0.0329 (12) | 0.0004 (12) | 0.0166 (11) | 0.0068 (10) |
C17 | 0.094 (4) | 0.0383 (16) | 0.055 (2) | −0.0152 (18) | 0.032 (2) | 0.0043 (14) |
C18 | 0.0464 (16) | 0.0446 (17) | 0.0277 (13) | −0.0039 (13) | 0.0021 (11) | −0.0075 (11) |
C19 | 0.084 (3) | 0.0471 (19) | 0.0406 (16) | −0.0257 (17) | 0.0088 (16) | −0.0057 (13) |
Br1—C13 | 1.9048 (19) | C11—H11A | 0.9500 |
P1—O1 | 1.4702 (14) | C12—C13 | 1.379 (3) |
P1—O2 | 1.5672 (15) | C12—H12A | 0.9500 |
P1—O3 | 1.5693 (14) | C13—C14 | 1.387 (3) |
P1—C1 | 1.8170 (18) | C14—C15 | 1.384 (3) |
O2—C16 | 1.457 (3) | C14—H14A | 0.9500 |
O3—C18 | 1.465 (3) | C15—H15A | 0.9500 |
O3—C18' | 1.47 (2) | C16—C17 | 1.483 (4) |
N1—C10 | 1.403 (2) | C16—H16A | 0.9900 |
N1—C1 | 1.461 (2) | C16—H16B | 0.9900 |
N1—H1B | 0.81 (2) | C17—H17A | 0.9800 |
C1—C2 | 1.528 (3) | C17—H17B | 0.9800 |
C1—H1A | 1.0000 | C17—H17C | 0.9800 |
C2—C7 | 1.387 (3) | C17'—H17D | 0.9800 |
C2—C3 | 1.394 (3) | C17'—H17E | 0.9800 |
C3—C4 | 1.384 (3) | C17'—H17F | 0.9800 |
C3—H3A | 0.9500 | C18—C19 | 1.478 (4) |
C4—C5 | 1.396 (3) | C18—H18A | 0.9900 |
C4—H4A | 0.9500 | C18—H18B | 0.9900 |
C5—C6 | 1.392 (3) | C18'—C19' | 1.45 (3) |
C5—C8 | 1.445 (3) | C18'—H18C | 0.9900 |
C6—C7 | 1.386 (3) | C18'—H18D | 0.9900 |
C6—H6A | 0.9500 | C19—H19A | 0.9800 |
C7—H7A | 0.9500 | C19—H19B | 0.9800 |
C8—C9 | 1.187 (3) | C19—H19C | 0.9800 |
C9—H9A | 0.9500 | C19'—H19D | 0.9800 |
C10—C11 | 1.397 (3) | C19'—H19E | 0.9800 |
C10—C15 | 1.398 (3) | C19'—H19F | 0.9800 |
C11—C12 | 1.394 (3) | ||
O1—P1—O2 | 115.50 (8) | C12—C13—Br1 | 119.37 (15) |
O1—P1—O3 | 115.20 (9) | C14—C13—Br1 | 119.95 (16) |
O2—P1—O3 | 103.91 (8) | C15—C14—C13 | 119.44 (19) |
O1—P1—C1 | 114.24 (8) | C15—C14—H14A | 120.3 |
O2—P1—C1 | 103.61 (8) | C13—C14—H14A | 120.3 |
O3—P1—C1 | 102.79 (8) | C14—C15—C10 | 121.28 (18) |
C16—O2—P1 | 123.23 (15) | C14—C15—H15A | 119.4 |
C18—O3—P1 | 122.84 (15) | C10—C15—H15A | 119.4 |
C18'—O3—P1 | 119.7 (8) | O2—C16—C17 | 110.2 (2) |
C10—N1—C1 | 118.78 (15) | O2—C16—H16A | 109.6 |
C10—N1—H1B | 112.9 (17) | C17—C16—H16A | 109.6 |
C1—N1—H1B | 113.0 (17) | O2—C16—H16B | 109.6 |
N1—C1—C2 | 115.29 (15) | C17—C16—H16B | 109.6 |
N1—C1—P1 | 109.55 (12) | H16A—C16—H16B | 108.1 |
C2—C1—P1 | 108.26 (12) | C16—C17—H17A | 109.5 |
N1—C1—H1A | 107.8 | C16—C17—H17B | 109.5 |
C2—C1—H1A | 107.8 | H17A—C17—H17B | 109.5 |
P1—C1—H1A | 107.8 | C16—C17—H17C | 109.5 |
C7—C2—C3 | 118.61 (18) | H17A—C17—H17C | 109.5 |
C7—C2—C1 | 121.57 (17) | H17B—C17—H17C | 109.5 |
C3—C2—C1 | 119.77 (16) | H17D—C17'—H17E | 109.5 |
C4—C3—C2 | 120.71 (19) | H17D—C17'—H17F | 109.5 |
C4—C3—H3A | 119.6 | H17E—C17'—H17F | 109.5 |
C2—C3—H3A | 119.6 | O3—C18—C19 | 113.4 (2) |
C3—C4—C5 | 120.59 (19) | O3—C18—H18A | 108.9 |
C3—C4—H4A | 119.7 | C19—C18—H18A | 108.9 |
C5—C4—H4A | 119.7 | O3—C18—H18B | 108.9 |
C6—C5—C4 | 118.63 (18) | C19—C18—H18B | 108.9 |
C6—C5—C8 | 121.66 (19) | H18A—C18—H18B | 107.7 |
C4—C5—C8 | 119.7 (2) | C19'—C18'—O3 | 113.0 (18) |
C7—C6—C5 | 120.52 (18) | C19'—C18'—H18C | 109.0 |
C7—C6—H6A | 119.7 | O3—C18'—H18C | 109.0 |
C5—C6—H6A | 119.7 | C19'—C18'—H18D | 109.0 |
C6—C7—C2 | 120.93 (18) | O3—C18'—H18D | 109.0 |
C6—C7—H7A | 119.5 | H18C—C18'—H18D | 107.8 |
C2—C7—H7A | 119.5 | C18—C19—H19A | 109.5 |
C9—C8—C5 | 178.1 (3) | C18—C19—H19B | 109.5 |
C8—C9—H9A | 180.0 | H19A—C19—H19B | 109.5 |
C11—C10—C15 | 118.14 (17) | C18—C19—H19C | 109.5 |
C11—C10—N1 | 122.78 (17) | H19A—C19—H19C | 109.5 |
C15—C10—N1 | 119.04 (17) | H19B—C19—H19C | 109.5 |
C12—C11—C10 | 120.77 (19) | C18'—C19'—H19D | 109.5 |
C12—C11—H11A | 119.6 | C18'—C19'—H19E | 109.5 |
C10—C11—H11A | 119.6 | H19D—C19'—H19E | 109.5 |
C13—C12—C11 | 119.68 (19) | C18'—C19'—H19F | 109.5 |
C13—C12—H12A | 120.2 | H19D—C19'—H19F | 109.5 |
C11—C12—H12A | 120.2 | H19E—C19'—H19F | 109.5 |
C12—C13—C14 | 120.67 (18) | ||
O1—P1—O2—C16 | 20.18 (19) | C2—C3—C4—C5 | −0.8 (3) |
O3—P1—O2—C16 | 147.35 (16) | C3—C4—C5—C6 | 1.4 (3) |
C1—P1—O2—C16 | −105.52 (17) | C3—C4—C5—C8 | −178.4 (2) |
O1—P1—O3—C18 | 30.9 (2) | C4—C5—C6—C7 | −1.1 (3) |
O2—P1—O3—C18 | −96.40 (19) | C8—C5—C6—C7 | 178.61 (19) |
C1—P1—O3—C18 | 155.86 (19) | C5—C6—C7—C2 | 0.2 (3) |
O1—P1—O3—C18' | 72.9 (11) | C3—C2—C7—C6 | 0.4 (3) |
O2—P1—O3—C18' | −54.5 (11) | C1—C2—C7—C6 | 177.76 (18) |
C1—P1—O3—C18' | −162.2 (11) | C1—N1—C10—C11 | −26.6 (3) |
C10—N1—C1—C2 | −64.5 (2) | C1—N1—C10—C15 | 155.68 (17) |
C10—N1—C1—P1 | 173.11 (13) | C15—C10—C11—C12 | −0.4 (3) |
O1—P1—C1—N1 | 62.67 (15) | N1—C10—C11—C12 | −178.19 (18) |
O2—P1—C1—N1 | −170.84 (12) | C10—C11—C12—C13 | −0.7 (3) |
O3—P1—C1—N1 | −62.87 (14) | C11—C12—C13—C14 | 1.2 (3) |
O1—P1—C1—C2 | −63.81 (15) | C11—C12—C13—Br1 | −178.00 (15) |
O2—P1—C1—C2 | 62.69 (13) | C12—C13—C14—C15 | −0.4 (3) |
O3—P1—C1—C2 | 170.66 (12) | Br1—C13—C14—C15 | 178.72 (15) |
N1—C1—C2—C7 | 132.71 (18) | C13—C14—C15—C10 | −0.7 (3) |
P1—C1—C2—C7 | −104.23 (18) | C11—C10—C15—C14 | 1.2 (3) |
N1—C1—C2—C3 | −50.0 (2) | N1—C10—C15—C14 | 179.01 (18) |
P1—C1—C2—C3 | 73.1 (2) | P1—O2—C16—C17 | −102.3 (3) |
C7—C2—C3—C4 | −0.1 (3) | P1—O3—C18—C19 | 76.9 (3) |
C1—C2—C3—C4 | −177.55 (19) | P1—O3—C18'—C19' | −70.8 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···O1i | 0.81 (2) | 2.20 (2) | 2.981 (2) | 162 (2) |
C3—H3A···O1i | 0.95 | 2.59 | 3.481 (3) | 156 |
C15—H15A···O1i | 0.95 | 2.55 | 3.254 (2) | 131 |
C9—H9A···N1ii | 0.95 | 2.60 | 3.542 (3) | 172 |
C12—H12A···O3iii | 0.95 | 2.50 | 3.398 (2) | 157 |
C4—H4A···Br1iv | 0.95 | 3.25 | 3.968 (2) | 134 |
C18—H18B···Br1v | 0.99 | 3.19 | 3.920 (3) | 132 |
C17—H17A···C11vi | 0.98 | 2.84 | 3.786 (4) | 161 |
C17—H17A···C12vi | 0.98 | 2.74 | 3.646 (4) | 153 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x, y, z−1; (iii) −x+1, −y+1, −z+1; (iv) x+1/2, −y+1/2, z−1/2; (v) −x+3/2, y+1/2, −z+3/2; (vi) −x+3/2, y+1/2, −z+1/2. |
C23H31ClNO3PSi | F(000) = 1968 |
Mr = 464.00 | Dx = 1.204 Mg m−3 |
Monoclinic, I2/a | Melting point: 371(1) K |
Hall symbol: -I 2ya | Mo Kα radiation, λ = 0.71073 Å |
a = 17.3791 (16) Å | Cell parameters from 5632 reflections |
b = 14.7131 (13) Å | θ = 3–25° |
c = 20.019 (3) Å | µ = 0.28 mm−1 |
β = 90.464 (1)° | T = 183 K |
V = 5118.6 (10) Å3 | Block, pale brown |
Z = 8 | 0.38 × 0.36 × 0.34 mm |
Siemens SMART 1K CCD area-detector diffractometer | 5021 independent reflections |
Radiation source: normal-focus sealed tube | 3655 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.085 |
ω scans | θmax = 26.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | h = −21→21 |
Tmin = 0.790, Tmax = 0.909 | k = −18→18 |
24553 measured reflections | l = −24→24 |
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)] = 0.101 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.181 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.20 | w = 1/[σ2(Fo2) + (0.04P)2 + 12P] where P = (Fo2 + 2Fc2)/3 |
5021 reflections | (Δ/σ)max = 0.001 |
297 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C23H31ClNO3PSi | V = 5118.6 (10) Å3 |
Mr = 464.00 | Z = 8 |
Monoclinic, I2/a | Mo Kα radiation |
a = 17.3791 (16) Å | µ = 0.28 mm−1 |
b = 14.7131 (13) Å | T = 183 K |
c = 20.019 (3) Å | 0.38 × 0.36 × 0.34 mm |
β = 90.464 (1)° |
Siemens SMART 1K CCD area-detector diffractometer | 5021 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | 3655 reflections with I > 2σ(I) |
Tmin = 0.790, Tmax = 0.909 | Rint = 0.085 |
24553 measured reflections |
R[F2 > 2σ(F2)] = 0.101 | 0 restraints |
wR(F2) = 0.181 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.20 | w = 1/[σ2(Fo2) + (0.04P)2 + 12P] where P = (Fo2 + 2Fc2)/3 |
5021 reflections | Δρmax = 0.39 e Å−3 |
297 parameters | Δρmin = −0.27 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cl1 | 0.68735 (6) | 0.76247 (11) | 0.43042 (7) | 0.0803 (5) | |
P1 | 0.20317 (6) | 0.73870 (8) | 0.38093 (6) | 0.0451 (3) | |
Si1 | 0.39549 (7) | 0.13406 (9) | 0.32089 (7) | 0.0559 (4) | |
O1 | 0.18631 (16) | 0.7528 (2) | 0.30989 (16) | 0.0634 (10) | |
O2 | 0.15600 (14) | 0.66097 (19) | 0.41600 (13) | 0.0419 (7) | |
O3 | 0.18498 (19) | 0.8192 (2) | 0.42940 (19) | 0.0726 (11) | |
N1 | 0.35325 (19) | 0.7771 (2) | 0.36837 (19) | 0.0448 (9) | |
H1B | 0.341 (3) | 0.785 (3) | 0.329 (2) | 0.054* | |
C1 | 0.3027 (2) | 0.7113 (3) | 0.4000 (2) | 0.0387 (10) | |
H1A | 0.3095 | 0.7189 | 0.4493 | 0.046* | |
C2 | 0.3207 (2) | 0.6124 (3) | 0.38435 (19) | 0.0362 (9) | |
C3 | 0.3332 (2) | 0.5839 (3) | 0.3192 (2) | 0.0426 (10) | |
H3A | 0.3311 | 0.6267 | 0.2837 | 0.051* | |
C4 | 0.3487 (2) | 0.4940 (3) | 0.3056 (2) | 0.0449 (11) | |
H4A | 0.3581 | 0.4755 | 0.2609 | 0.054* | |
C5 | 0.3505 (2) | 0.4296 (3) | 0.3572 (2) | 0.0408 (10) | |
C6 | 0.3375 (2) | 0.4582 (3) | 0.4220 (2) | 0.0432 (10) | |
H6A | 0.3382 | 0.4154 | 0.4575 | 0.052* | |
C7 | 0.3234 (2) | 0.5486 (3) | 0.4353 (2) | 0.0394 (10) | |
H7A | 0.3154 | 0.5675 | 0.4801 | 0.047* | |
C8 | 0.3667 (2) | 0.3345 (3) | 0.3442 (2) | 0.0481 (11) | |
C9 | 0.3810 (2) | 0.2562 (3) | 0.3345 (2) | 0.0540 (12) | |
C10 | 0.4323 (2) | 0.7740 (3) | 0.3838 (2) | 0.0374 (9) | |
C11 | 0.4596 (2) | 0.7372 (3) | 0.4436 (2) | 0.0509 (11) | |
H11A | 0.4240 | 0.7129 | 0.4746 | 0.061* | |
C12 | 0.5372 (2) | 0.7353 (3) | 0.4586 (2) | 0.0530 (12) | |
H12A | 0.5547 | 0.7108 | 0.5000 | 0.064* | |
C13 | 0.5888 (2) | 0.7687 (3) | 0.4137 (2) | 0.0485 (11) | |
C14 | 0.5630 (2) | 0.8072 (3) | 0.3547 (2) | 0.0457 (11) | |
H14A | 0.5992 | 0.8316 | 0.3243 | 0.055* | |
C15 | 0.4853 (2) | 0.8109 (3) | 0.33909 (19) | 0.0363 (9) | |
C16 | 0.1316 (3) | 0.5798 (3) | 0.3817 (2) | 0.0613 (13) | |
H16A | 0.1675 | 0.5294 | 0.3923 | 0.074* | |
H16B | 0.1325 | 0.5901 | 0.3329 | 0.074* | |
C17 | 0.0535 (3) | 0.5549 (4) | 0.4023 (3) | 0.0814 (18) | |
H17A | 0.0376 | 0.4993 | 0.3790 | 0.122* | |
H17B | 0.0179 | 0.6043 | 0.3909 | 0.122* | |
H17C | 0.0528 | 0.5445 | 0.4506 | 0.122* | |
C18 | 0.1974 (7) | 0.9058 (7) | 0.4043 (6) | 0.082 (4) | 0.518 (12) |
H18A | 0.1774 | 0.9121 | 0.3580 | 0.099* | 0.518 (12) |
H18B | 0.2527 | 0.9222 | 0.4054 | 0.099* | 0.518 (12) |
C18' | 0.1246 (6) | 0.8825 (7) | 0.4340 (6) | 0.063 (4) | 0.482 (12) |
H18C | 0.1091 | 0.8871 | 0.4813 | 0.076* | 0.482 (12) |
H18D | 0.0799 | 0.8590 | 0.4084 | 0.076* | 0.482 (12) |
C19 | 0.1513 (13) | 0.9624 (13) | 0.4532 (11) | 0.126 (8) | 0.518 (12) |
H19A | 0.1549 | 1.0268 | 0.4410 | 0.189* | 0.518 (12) |
H19B | 0.1721 | 0.9538 | 0.4985 | 0.189* | 0.518 (12) |
H19C | 0.0974 | 0.9432 | 0.4518 | 0.189* | 0.518 (12) |
C19' | 0.1424 (13) | 0.9720 (12) | 0.4100 (10) | 0.095 (6) | 0.482 (12) |
H19D | 0.0966 | 1.0107 | 0.4132 | 0.142* | 0.482 (12) |
H19E | 0.1587 | 0.9684 | 0.3634 | 0.142* | 0.482 (12) |
H19F | 0.1840 | 0.9981 | 0.4372 | 0.142* | 0.482 (12) |
C20 | 0.4579 (2) | 0.8533 (3) | 0.2746 (2) | 0.0470 (11) | |
H20A | 0.4305 | 0.8076 | 0.2478 | 0.070* | |
H20B | 0.5022 | 0.8759 | 0.2495 | 0.070* | |
H20C | 0.4231 | 0.9039 | 0.2844 | 0.070* | |
C21 | 0.3942 (4) | 0.0769 (4) | 0.4033 (3) | 0.108 (2) | |
H21A | 0.3456 | 0.0903 | 0.4257 | 0.161* | |
H21B | 0.4372 | 0.0992 | 0.4307 | 0.161* | |
H21C | 0.3992 | 0.0112 | 0.3971 | 0.161* | |
C22 | 0.3139 (4) | 0.0938 (5) | 0.2698 (4) | 0.126 (3) | |
H22A | 0.3191 | 0.1167 | 0.2241 | 0.190* | |
H22B | 0.2657 | 0.1161 | 0.2889 | 0.190* | |
H22C | 0.3136 | 0.0272 | 0.2693 | 0.190* | |
C23 | 0.4876 (3) | 0.1160 (4) | 0.2790 (3) | 0.092 (2) | |
H23A | 0.4848 | 0.1410 | 0.2336 | 0.137* | |
H23B | 0.4985 | 0.0508 | 0.2768 | 0.137* | |
H23C | 0.5286 | 0.1467 | 0.3041 | 0.137* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0325 (6) | 0.1103 (12) | 0.0978 (11) | −0.0059 (7) | −0.0187 (6) | 0.0263 (9) |
P1 | 0.0269 (5) | 0.0496 (7) | 0.0589 (8) | 0.0088 (5) | 0.0064 (5) | 0.0228 (6) |
Si1 | 0.0431 (7) | 0.0488 (8) | 0.0757 (10) | 0.0008 (6) | 0.0029 (6) | −0.0147 (7) |
O1 | 0.0370 (16) | 0.080 (2) | 0.073 (2) | −0.0011 (15) | −0.0036 (15) | 0.0449 (19) |
O2 | 0.0318 (14) | 0.0486 (17) | 0.0453 (17) | 0.0014 (13) | 0.0049 (12) | 0.0122 (14) |
O3 | 0.061 (2) | 0.051 (2) | 0.106 (3) | 0.0261 (17) | 0.029 (2) | 0.0185 (19) |
N1 | 0.0302 (18) | 0.051 (2) | 0.053 (2) | 0.0038 (15) | −0.0017 (17) | 0.0214 (19) |
C1 | 0.031 (2) | 0.047 (2) | 0.039 (2) | 0.0053 (18) | 0.0004 (17) | 0.0114 (19) |
C2 | 0.0226 (18) | 0.047 (2) | 0.039 (2) | 0.0024 (17) | 0.0031 (16) | 0.0053 (19) |
C3 | 0.033 (2) | 0.053 (3) | 0.041 (3) | −0.0004 (19) | 0.0035 (18) | 0.010 (2) |
C4 | 0.039 (2) | 0.062 (3) | 0.033 (2) | −0.001 (2) | 0.0050 (18) | −0.003 (2) |
C5 | 0.030 (2) | 0.050 (3) | 0.042 (3) | 0.0058 (18) | 0.0013 (18) | −0.005 (2) |
C6 | 0.041 (2) | 0.049 (3) | 0.040 (3) | 0.012 (2) | 0.0011 (19) | 0.010 (2) |
C7 | 0.040 (2) | 0.048 (3) | 0.030 (2) | 0.0107 (19) | 0.0013 (17) | 0.0029 (19) |
C8 | 0.037 (2) | 0.057 (3) | 0.051 (3) | −0.001 (2) | 0.004 (2) | −0.006 (2) |
C9 | 0.042 (2) | 0.052 (3) | 0.068 (3) | 0.001 (2) | 0.006 (2) | −0.011 (2) |
C10 | 0.030 (2) | 0.036 (2) | 0.046 (2) | 0.0043 (17) | −0.0022 (17) | 0.0056 (18) |
C11 | 0.037 (2) | 0.066 (3) | 0.050 (3) | 0.005 (2) | 0.005 (2) | 0.017 (2) |
C12 | 0.040 (2) | 0.069 (3) | 0.050 (3) | 0.006 (2) | −0.009 (2) | 0.011 (2) |
C13 | 0.028 (2) | 0.058 (3) | 0.059 (3) | −0.001 (2) | −0.008 (2) | 0.004 (2) |
C14 | 0.032 (2) | 0.053 (3) | 0.052 (3) | −0.0050 (19) | 0.003 (2) | 0.006 (2) |
C15 | 0.033 (2) | 0.033 (2) | 0.042 (2) | 0.0000 (17) | −0.0007 (18) | 0.0012 (18) |
C16 | 0.063 (3) | 0.072 (3) | 0.049 (3) | −0.005 (3) | 0.000 (2) | 0.011 (3) |
C17 | 0.051 (3) | 0.123 (5) | 0.070 (4) | −0.022 (3) | −0.001 (3) | 0.001 (3) |
C18 | 0.087 (9) | 0.054 (7) | 0.106 (9) | −0.007 (6) | 0.007 (7) | −0.013 (6) |
C18' | 0.046 (6) | 0.054 (7) | 0.090 (8) | 0.024 (5) | −0.014 (5) | −0.014 (6) |
C19 | 0.158 (16) | 0.069 (12) | 0.150 (19) | 0.040 (10) | −0.038 (17) | −0.038 (13) |
C19' | 0.115 (13) | 0.051 (8) | 0.118 (15) | 0.025 (8) | −0.011 (13) | 0.019 (11) |
C20 | 0.043 (2) | 0.053 (3) | 0.045 (3) | −0.005 (2) | −0.0019 (19) | 0.010 (2) |
C21 | 0.139 (6) | 0.079 (4) | 0.106 (5) | −0.003 (4) | 0.030 (5) | −0.002 (4) |
C22 | 0.087 (5) | 0.094 (5) | 0.197 (8) | 0.010 (4) | −0.051 (5) | −0.066 (5) |
C23 | 0.071 (4) | 0.061 (4) | 0.144 (6) | 0.007 (3) | 0.036 (4) | −0.003 (4) |
Cl1—C13 | 1.745 (4) | C13—C14 | 1.382 (6) |
P1—O1 | 1.464 (3) | C14—C15 | 1.384 (5) |
P1—O3 | 1.565 (4) | C14—H14A | 0.9500 |
P1—O2 | 1.575 (3) | C15—C20 | 1.508 (5) |
P1—C1 | 1.814 (4) | C16—C17 | 1.469 (6) |
Si1—C23 | 1.832 (5) | C16—H16A | 0.9900 |
Si1—C9 | 1.835 (5) | C16—H16B | 0.9900 |
Si1—C22 | 1.839 (6) | C17—H17A | 0.9800 |
Si1—C21 | 1.852 (6) | C17—H17B | 0.9800 |
O2—C16 | 1.440 (5) | C17—H17C | 0.9800 |
O3—C18 | 1.388 (11) | C18—C19 | 1.52 (2) |
O3—C18' | 1.406 (9) | C18—H18A | 0.9900 |
N1—C10 | 1.407 (5) | C18—H18B | 0.9900 |
N1—C1 | 1.456 (5) | C18'—C19' | 1.44 (2) |
N1—H1B | 0.81 (4) | C18'—H18C | 0.9900 |
C1—C2 | 1.521 (5) | C18'—H18D | 0.9900 |
C1—H1A | 1.0000 | C19—H19A | 0.9800 |
C2—C7 | 1.387 (5) | C19—H19B | 0.9800 |
C2—C3 | 1.389 (5) | C19—H19C | 0.9800 |
C3—C4 | 1.377 (6) | C19'—H19D | 0.9800 |
C3—H3A | 0.9500 | C19'—H19E | 0.9800 |
C4—C5 | 1.403 (6) | C19'—H19F | 0.9800 |
C4—H4A | 0.9500 | C20—H20A | 0.9800 |
C5—C6 | 1.385 (6) | C20—H20B | 0.9800 |
C5—C8 | 1.451 (6) | C20—H20C | 0.9800 |
C6—C7 | 1.378 (5) | C21—H21A | 0.9800 |
C6—H6A | 0.9500 | C21—H21B | 0.9800 |
C7—H7A | 0.9500 | C21—H21C | 0.9800 |
C8—C9 | 1.194 (6) | C22—H22A | 0.9800 |
C10—C11 | 1.393 (6) | C22—H22B | 0.9800 |
C10—C15 | 1.399 (5) | C22—H22C | 0.9800 |
C11—C12 | 1.381 (6) | C23—H23A | 0.9800 |
C11—H11A | 0.9500 | C23—H23B | 0.9800 |
C12—C13 | 1.366 (6) | C23—H23C | 0.9800 |
C12—H12A | 0.9500 | ||
O1—P1—O3 | 117.06 (19) | C10—C15—C20 | 120.2 (3) |
O1—P1—O2 | 115.77 (17) | O2—C16—C17 | 110.0 (4) |
O3—P1—O2 | 99.49 (17) | O2—C16—H16A | 109.7 |
O1—P1—C1 | 114.77 (18) | C17—C16—H16A | 109.7 |
O3—P1—C1 | 103.59 (19) | O2—C16—H16B | 109.7 |
O2—P1—C1 | 104.08 (16) | C17—C16—H16B | 109.7 |
C23—Si1—C9 | 109.4 (2) | H16A—C16—H16B | 108.2 |
C23—Si1—C22 | 111.8 (3) | C16—C17—H17A | 109.5 |
C9—Si1—C22 | 106.9 (3) | C16—C17—H17B | 109.5 |
C23—Si1—C21 | 111.0 (3) | H17A—C17—H17B | 109.5 |
C9—Si1—C21 | 108.0 (3) | C16—C17—H17C | 109.5 |
C22—Si1—C21 | 109.6 (4) | H17A—C17—H17C | 109.5 |
C16—O2—P1 | 122.8 (3) | H17B—C17—H17C | 109.5 |
C18—O3—P1 | 115.9 (5) | O3—C18—C19 | 100.6 (12) |
C18'—O3—P1 | 134.1 (5) | O3—C18—H18A | 111.6 |
C10—N1—C1 | 118.4 (3) | C19—C18—H18A | 111.6 |
C10—N1—H1B | 117 (3) | O3—C18—H18B | 111.6 |
C1—N1—H1B | 111 (3) | C19—C18—H18B | 111.6 |
N1—C1—C2 | 114.9 (3) | H18A—C18—H18B | 109.4 |
N1—C1—P1 | 109.8 (3) | O3—C18'—C19' | 115.0 (12) |
C2—C1—P1 | 111.5 (3) | O3—C18'—H18C | 108.5 |
N1—C1—H1A | 106.7 | C19'—C18'—H18C | 108.5 |
C2—C1—H1A | 106.7 | O3—C18'—H18D | 108.5 |
P1—C1—H1A | 106.7 | C19'—C18'—H18D | 108.5 |
C7—C2—C3 | 118.8 (4) | H18C—C18'—H18D | 107.5 |
C7—C2—C1 | 120.1 (4) | C18—C19—H19A | 109.5 |
C3—C2—C1 | 121.1 (4) | C18—C19—H19B | 109.5 |
C4—C3—C2 | 120.5 (4) | H19A—C19—H19B | 109.5 |
C4—C3—H3A | 119.7 | C18—C19—H19C | 109.5 |
C2—C3—H3A | 119.7 | H19A—C19—H19C | 109.5 |
C3—C4—C5 | 120.5 (4) | H19B—C19—H19C | 109.5 |
C3—C4—H4A | 119.8 | C18'—C19'—H19D | 109.5 |
C5—C4—H4A | 119.8 | C18'—C19'—H19E | 109.5 |
C6—C5—C4 | 118.8 (4) | H19D—C19'—H19E | 109.5 |
C6—C5—C8 | 119.7 (4) | C18'—C19'—H19F | 109.5 |
C4—C5—C8 | 121.6 (4) | H19D—C19'—H19F | 109.5 |
C7—C6—C5 | 120.3 (4) | H19E—C19'—H19F | 109.5 |
C7—C6—H6A | 119.8 | C15—C20—H20A | 109.5 |
C5—C6—H6A | 119.8 | C15—C20—H20B | 109.5 |
C6—C7—C2 | 121.1 (4) | H20A—C20—H20B | 109.5 |
C6—C7—H7A | 119.5 | C15—C20—H20C | 109.5 |
C2—C7—H7A | 119.5 | H20A—C20—H20C | 109.5 |
C9—C8—C5 | 178.9 (5) | H20B—C20—H20C | 109.5 |
C8—C9—Si1 | 175.8 (4) | Si1—C21—H21A | 109.5 |
C11—C10—C15 | 118.7 (4) | Si1—C21—H21B | 109.5 |
C11—C10—N1 | 121.7 (4) | H21A—C21—H21B | 109.5 |
C15—C10—N1 | 119.6 (3) | Si1—C21—H21C | 109.5 |
C12—C11—C10 | 121.3 (4) | H21A—C21—H21C | 109.5 |
C12—C11—H11A | 119.3 | H21B—C21—H21C | 109.5 |
C10—C11—H11A | 119.3 | Si1—C22—H22A | 109.5 |
C13—C12—C11 | 119.6 (4) | Si1—C22—H22B | 109.5 |
C13—C12—H12A | 120.2 | H22A—C22—H22B | 109.5 |
C11—C12—H12A | 120.2 | Si1—C22—H22C | 109.5 |
C12—C13—C14 | 120.0 (4) | H22A—C22—H22C | 109.5 |
C12—C13—Cl1 | 120.2 (3) | H22B—C22—H22C | 109.5 |
C14—C13—Cl1 | 119.8 (3) | Si1—C23—H23A | 109.5 |
C13—C14—C15 | 121.2 (4) | Si1—C23—H23B | 109.5 |
C13—C14—H14A | 119.4 | H23A—C23—H23B | 109.5 |
C15—C14—H14A | 119.4 | Si1—C23—H23C | 109.5 |
C14—C15—C10 | 119.1 (4) | H23A—C23—H23C | 109.5 |
C14—C15—C20 | 120.7 (4) | H23B—C23—H23C | 109.5 |
O1—P1—O2—C16 | 32.7 (4) | C3—C4—C5—C8 | −180.0 (4) |
O3—P1—O2—C16 | 159.1 (3) | C4—C5—C6—C7 | −0.4 (6) |
C1—P1—O2—C16 | −94.2 (3) | C8—C5—C6—C7 | 178.8 (4) |
O1—P1—O3—C18 | −35.7 (7) | C5—C6—C7—C2 | 1.1 (6) |
O2—P1—O3—C18 | −161.1 (6) | C3—C2—C7—C6 | −0.6 (6) |
C1—P1—O3—C18 | 91.8 (6) | C1—C2—C7—C6 | 178.2 (3) |
O1—P1—O3—C18' | 39.9 (8) | C1—N1—C10—C11 | −24.6 (6) |
O2—P1—O3—C18' | −85.6 (8) | C1—N1—C10—C15 | 157.0 (4) |
C1—P1—O3—C18' | 167.3 (7) | C15—C10—C11—C12 | −1.0 (7) |
C10—N1—C1—C2 | −61.0 (5) | N1—C10—C11—C12 | −179.4 (4) |
C10—N1—C1—P1 | 172.4 (3) | C10—C11—C12—C13 | −1.1 (7) |
O1—P1—C1—N1 | 50.7 (4) | C11—C12—C13—C14 | 2.4 (7) |
O3—P1—C1—N1 | −78.2 (3) | C11—C12—C13—Cl1 | −177.3 (4) |
O2—P1—C1—N1 | 178.2 (3) | C12—C13—C14—C15 | −1.6 (7) |
O1—P1—C1—C2 | −77.8 (3) | Cl1—C13—C14—C15 | 178.2 (3) |
O3—P1—C1—C2 | 153.4 (3) | C13—C14—C15—C10 | −0.6 (6) |
O2—P1—C1—C2 | 49.8 (3) | C13—C14—C15—C20 | 179.9 (4) |
N1—C1—C2—C7 | 133.7 (4) | C11—C10—C15—C14 | 1.8 (6) |
P1—C1—C2—C7 | −100.6 (4) | N1—C10—C15—C14 | −179.7 (4) |
N1—C1—C2—C3 | −47.5 (5) | C11—C10—C15—C20 | −178.7 (4) |
P1—C1—C2—C3 | 78.2 (4) | N1—C10—C15—C20 | −0.2 (6) |
C7—C2—C3—C4 | −0.5 (6) | P1—O2—C16—C17 | −140.1 (3) |
C1—C2—C3—C4 | −179.3 (3) | P1—O3—C18—C19 | 162.8 (9) |
C2—C3—C4—C5 | 1.2 (6) | P1—O3—C18'—C19' | −103.2 (12) |
C3—C4—C5—C6 | −0.8 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3A···O1i | 0.95 | 2.60 | 3.543 (5) | 175 |
C7—H7A···O2ii | 0.95 | 2.54 | 3.421 (5) | 155 |
C20—H20A···O1i | 0.98 | 2.49 | 3.392 (5) | 153 |
Symmetry codes: (i) −x+1/2, −y+3/2, −z+1/2; (ii) −x+1/2, y, −z+1. |
C22H29FNO3PSi | Z = 2 |
Mr = 433.52 | F(000) = 460 |
Triclinic, P1 | Dx = 1.257 Mg m−3 |
Hall symbol: -P 1 | Melting point: 420(1) K |
a = 8.9633 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.1726 (9) Å | Cell parameters from 7350 reflections |
c = 12.6997 (10) Å | θ = 3–25° |
α = 69.980 (1)° | µ = 0.20 mm−1 |
β = 87.263 (1)° | T = 184 K |
γ = 73.667 (1)° | Block, pale brown |
V = 1145.06 (16) Å3 | 0.40 × 0.40 × 0.30 mm |
Siemens SMART 1K CCD area-detector diffractometer | 4782 independent reflections |
Radiation source: normal-focus sealed tube | 3504 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.064 |
ω scans | θmax = 27.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | h = −11→11 |
Tmin = 0.852, Tmax = 0.941 | k = −14→14 |
12221 measured reflections | l = −16→15 |
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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.148 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.067P)2] where P = (Fo2 + 2Fc2)/3 |
4782 reflections | (Δ/σ)max < 0.001 |
271 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
C22H29FNO3PSi | γ = 73.667 (1)° |
Mr = 433.52 | V = 1145.06 (16) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.9633 (7) Å | Mo Kα radiation |
b = 11.1726 (9) Å | µ = 0.20 mm−1 |
c = 12.6997 (10) Å | T = 184 K |
α = 69.980 (1)° | 0.40 × 0.40 × 0.30 mm |
β = 87.263 (1)° |
Siemens SMART 1K CCD area-detector diffractometer | 4782 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | 3504 reflections with I > 2σ(I) |
Tmin = 0.852, Tmax = 0.941 | Rint = 0.064 |
12221 measured reflections |
R[F2 > 2σ(F2)] = 0.061 | 0 restraints |
wR(F2) = 0.148 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.37 e Å−3 |
4782 reflections | Δρmin = −0.39 e Å−3 |
271 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
P1 | 0.44796 (8) | 0.79898 (7) | 0.44261 (5) | 0.02109 (19) | |
Si1 | 1.32304 (9) | 0.26686 (7) | 0.97006 (6) | 0.0252 (2) | |
F1 | 0.0799 (2) | 0.83978 (18) | 1.02839 (14) | 0.0449 (5) | |
O1 | 0.4981 (2) | 0.92061 (17) | 0.40445 (15) | 0.0279 (4) | |
O2 | 0.5577 (2) | 0.67519 (17) | 0.41834 (15) | 0.0266 (4) | |
O3 | 0.2932 (2) | 0.80477 (18) | 0.38553 (15) | 0.0297 (5) | |
N1 | 0.3440 (3) | 0.8614 (2) | 0.62068 (18) | 0.0231 (5) | |
H1B | 0.392 (4) | 0.924 (3) | 0.601 (2) | 0.039 (9)* | |
C1 | 0.4263 (3) | 0.7429 (2) | 0.5946 (2) | 0.0220 (6) | |
H1A | 0.3572 | 0.6830 | 0.6117 | 0.026* | |
C2 | 0.5820 (3) | 0.6633 (2) | 0.6590 (2) | 0.0207 (6) | |
C3 | 0.6891 (3) | 0.7256 (3) | 0.6739 (2) | 0.0257 (6) | |
H3A | 0.6633 | 0.8198 | 0.6468 | 0.031* | |
C4 | 0.8337 (3) | 0.6516 (3) | 0.7280 (2) | 0.0275 (6) | |
H4A | 0.9065 | 0.6956 | 0.7364 | 0.033* | |
C5 | 0.8732 (3) | 0.5129 (3) | 0.7701 (2) | 0.0263 (6) | |
C6 | 0.7656 (3) | 0.4501 (3) | 0.7548 (2) | 0.0291 (6) | |
H6A | 0.7906 | 0.3559 | 0.7824 | 0.035* | |
C7 | 0.6220 (3) | 0.5252 (3) | 0.6992 (2) | 0.0272 (6) | |
H7A | 0.5500 | 0.4816 | 0.6885 | 0.033* | |
C8 | 1.0212 (3) | 0.4358 (3) | 0.8306 (2) | 0.0287 (6) | |
C9 | 1.1429 (3) | 0.3699 (3) | 0.8824 (2) | 0.0306 (7) | |
C10 | 0.2815 (3) | 0.8494 (3) | 0.7272 (2) | 0.0218 (6) | |
C11 | 0.2295 (3) | 0.7412 (3) | 0.7907 (2) | 0.0257 (6) | |
H11A | 0.2413 | 0.6689 | 0.7648 | 0.031* | |
C12 | 0.1603 (3) | 0.7380 (3) | 0.8920 (2) | 0.0305 (7) | |
H12A | 0.1242 | 0.6646 | 0.9350 | 0.037* | |
C13 | 0.1454 (3) | 0.8426 (3) | 0.9282 (2) | 0.0292 (6) | |
C14 | 0.1952 (3) | 0.9512 (3) | 0.8674 (2) | 0.0312 (7) | |
H14A | 0.1821 | 1.0232 | 0.8939 | 0.037* | |
C15 | 0.2643 (3) | 0.9540 (3) | 0.7673 (2) | 0.0276 (6) | |
H15A | 0.3005 | 1.0278 | 0.7254 | 0.033* | |
C16 | 0.7250 (3) | 0.6572 (3) | 0.4094 (2) | 0.0301 (6) | |
H16A | 0.7659 | 0.6827 | 0.4671 | 0.036* | |
H16B | 0.7465 | 0.7137 | 0.3345 | 0.036* | |
C17 | 0.8015 (3) | 0.5135 (3) | 0.4264 (3) | 0.0415 (8) | |
H17A | 0.9148 | 0.4975 | 0.4258 | 0.062* | |
H17B | 0.7656 | 0.4909 | 0.3659 | 0.062* | |
H17C | 0.7741 | 0.4583 | 0.4988 | 0.062* | |
C18 | 0.1491 (3) | 0.9122 (3) | 0.3746 (3) | 0.0368 (7) | |
H18A | 0.1057 | 0.9493 | 0.2961 | 0.044* | |
H18B | 0.1719 | 0.9843 | 0.3937 | 0.044* | |
C19 | 0.0330 (4) | 0.8595 (3) | 0.4517 (3) | 0.0454 (8) | |
H19A | −0.0655 | 0.9297 | 0.4403 | 0.068* | |
H19B | 0.0728 | 0.8295 | 0.5297 | 0.068* | |
H19C | 0.0155 | 0.7846 | 0.4355 | 0.068* | |
C20 | 1.4639 (3) | 0.1870 (3) | 0.8846 (2) | 0.0366 (7) | |
H20A | 1.4831 | 0.2556 | 0.8172 | 0.055* | |
H20B | 1.4206 | 0.1271 | 0.8626 | 0.055* | |
H20C | 1.5620 | 0.1363 | 0.9290 | 0.055* | |
C21 | 1.4063 (3) | 0.3772 (3) | 1.0138 (3) | 0.0355 (7) | |
H21A | 1.4389 | 0.4390 | 0.9477 | 0.053* | |
H21B | 1.4966 | 0.3237 | 1.0661 | 0.053* | |
H21C | 1.3276 | 0.4274 | 1.0509 | 0.053* | |
C22 | 1.2707 (3) | 0.1406 (3) | 1.0937 (2) | 0.0324 (7) | |
H22A | 1.1849 | 0.1847 | 1.1303 | 0.049* | |
H22B | 1.3612 | 0.0934 | 1.1469 | 0.049* | |
H22C | 1.2384 | 0.0771 | 1.0690 | 0.049* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0179 (4) | 0.0225 (4) | 0.0216 (4) | −0.0044 (3) | 0.0003 (3) | −0.0070 (3) |
Si1 | 0.0197 (4) | 0.0242 (4) | 0.0281 (4) | −0.0011 (3) | −0.0042 (3) | −0.0082 (3) |
F1 | 0.0490 (11) | 0.0537 (12) | 0.0304 (10) | −0.0142 (9) | 0.0181 (8) | −0.0147 (8) |
O1 | 0.0299 (11) | 0.0254 (10) | 0.0279 (10) | −0.0090 (8) | 0.0053 (8) | −0.0081 (8) |
O2 | 0.0215 (10) | 0.0292 (10) | 0.0329 (11) | −0.0071 (8) | 0.0036 (8) | −0.0157 (9) |
O3 | 0.0212 (10) | 0.0345 (11) | 0.0316 (11) | −0.0035 (9) | −0.0048 (8) | −0.0117 (9) |
N1 | 0.0213 (12) | 0.0211 (12) | 0.0242 (12) | −0.0041 (10) | 0.0017 (9) | −0.0059 (10) |
C1 | 0.0206 (14) | 0.0200 (13) | 0.0246 (14) | −0.0051 (11) | 0.0012 (11) | −0.0070 (11) |
C2 | 0.0186 (13) | 0.0240 (14) | 0.0165 (13) | −0.0005 (11) | 0.0023 (10) | −0.0076 (11) |
C3 | 0.0256 (15) | 0.0234 (14) | 0.0260 (14) | −0.0040 (12) | −0.0009 (11) | −0.0078 (12) |
C4 | 0.0219 (15) | 0.0320 (16) | 0.0292 (15) | −0.0065 (12) | −0.0011 (11) | −0.0119 (12) |
C5 | 0.0208 (14) | 0.0293 (15) | 0.0238 (14) | 0.0004 (12) | −0.0010 (11) | −0.0088 (12) |
C6 | 0.0265 (15) | 0.0214 (14) | 0.0307 (15) | −0.0013 (12) | −0.0025 (12) | −0.0023 (12) |
C7 | 0.0222 (14) | 0.0258 (15) | 0.0310 (15) | −0.0059 (12) | −0.0036 (11) | −0.0066 (12) |
C8 | 0.0245 (15) | 0.0314 (16) | 0.0280 (15) | −0.0048 (12) | 0.0021 (12) | −0.0101 (13) |
C9 | 0.0254 (15) | 0.0293 (16) | 0.0330 (16) | −0.0042 (13) | −0.0010 (12) | −0.0080 (13) |
C10 | 0.0124 (13) | 0.0252 (14) | 0.0217 (13) | −0.0007 (11) | −0.0011 (10) | −0.0042 (11) |
C11 | 0.0210 (14) | 0.0233 (14) | 0.0321 (16) | −0.0047 (11) | 0.0026 (12) | −0.0101 (12) |
C12 | 0.0256 (15) | 0.0280 (15) | 0.0320 (16) | −0.0076 (12) | 0.0052 (12) | −0.0036 (13) |
C13 | 0.0207 (15) | 0.0412 (17) | 0.0233 (14) | −0.0068 (13) | 0.0081 (11) | −0.0104 (13) |
C14 | 0.0308 (16) | 0.0340 (16) | 0.0324 (16) | −0.0079 (13) | 0.0038 (13) | −0.0172 (13) |
C15 | 0.0246 (15) | 0.0290 (15) | 0.0295 (15) | −0.0096 (12) | 0.0055 (12) | −0.0096 (12) |
C16 | 0.0184 (14) | 0.0389 (17) | 0.0373 (16) | −0.0079 (13) | 0.0067 (12) | −0.0194 (14) |
C17 | 0.0296 (18) | 0.0385 (18) | 0.048 (2) | −0.0007 (14) | 0.0110 (14) | −0.0129 (15) |
C18 | 0.0272 (16) | 0.0338 (17) | 0.0372 (17) | 0.0007 (13) | −0.0084 (13) | −0.0033 (14) |
C19 | 0.0255 (17) | 0.045 (2) | 0.055 (2) | −0.0029 (15) | 0.0000 (15) | −0.0094 (16) |
C20 | 0.0290 (16) | 0.0401 (18) | 0.0371 (17) | −0.0010 (14) | 0.0019 (13) | −0.0159 (14) |
C21 | 0.0315 (16) | 0.0340 (17) | 0.0401 (18) | −0.0062 (13) | −0.0037 (13) | −0.0135 (14) |
C22 | 0.0311 (16) | 0.0292 (15) | 0.0328 (16) | −0.0039 (13) | 0.0005 (13) | −0.0092 (13) |
P1—O1 | 1.4679 (19) | C11—C12 | 1.395 (4) |
P1—O3 | 1.5710 (18) | C11—H11A | 0.9500 |
P1—O2 | 1.5725 (18) | C12—C13 | 1.367 (4) |
P1—C1 | 1.833 (3) | C12—H12A | 0.9500 |
Si1—C21 | 1.847 (3) | C13—C14 | 1.377 (4) |
Si1—C9 | 1.849 (3) | C14—C15 | 1.382 (4) |
Si1—C22 | 1.861 (3) | C14—H14A | 0.9500 |
Si1—C20 | 1.862 (3) | C15—H15A | 0.9500 |
F1—C13 | 1.369 (3) | C16—C17 | 1.501 (4) |
O2—C16 | 1.460 (3) | C16—H16A | 0.9900 |
O3—C18 | 1.469 (3) | C16—H16B | 0.9900 |
N1—C10 | 1.417 (3) | C17—H17A | 0.9800 |
N1—C1 | 1.461 (3) | C17—H17B | 0.9800 |
N1—H1B | 0.88 (3) | C17—H17C | 0.9800 |
C1—C2 | 1.523 (3) | C18—C19 | 1.498 (4) |
C1—H1A | 1.0000 | C18—H18A | 0.9900 |
C2—C3 | 1.388 (4) | C18—H18B | 0.9900 |
C2—C7 | 1.392 (4) | C19—H19A | 0.9800 |
C3—C4 | 1.388 (4) | C19—H19B | 0.9800 |
C3—H3A | 0.9500 | C19—H19C | 0.9800 |
C4—C5 | 1.398 (4) | C20—H20A | 0.9800 |
C4—H4A | 0.9500 | C20—H20B | 0.9800 |
C5—C6 | 1.398 (4) | C20—H20C | 0.9800 |
C5—C8 | 1.447 (4) | C21—H21A | 0.9800 |
C6—C7 | 1.390 (4) | C21—H21B | 0.9800 |
C6—H6A | 0.9500 | C21—H21C | 0.9800 |
C7—H7A | 0.9500 | C22—H22A | 0.9800 |
C8—C9 | 1.205 (4) | C22—H22B | 0.9800 |
C10—C11 | 1.394 (4) | C22—H22C | 0.9800 |
C10—C15 | 1.395 (4) | ||
O1—P1—O3 | 116.73 (11) | C12—C13—F1 | 119.3 (2) |
O1—P1—O2 | 116.52 (11) | C12—C13—C14 | 122.1 (3) |
O3—P1—O2 | 98.15 (10) | F1—C13—C14 | 118.6 (2) |
O1—P1—C1 | 111.35 (11) | C13—C14—C15 | 119.1 (2) |
O3—P1—C1 | 107.21 (11) | C13—C14—H14A | 120.5 |
O2—P1—C1 | 105.52 (11) | C15—C14—H14A | 120.5 |
C21—Si1—C9 | 107.99 (13) | C14—C15—C10 | 120.7 (3) |
C21—Si1—C22 | 111.10 (14) | C14—C15—H15A | 119.7 |
C9—Si1—C22 | 108.04 (13) | C10—C15—H15A | 119.7 |
C21—Si1—C20 | 109.43 (14) | O2—C16—C17 | 107.8 (2) |
C9—Si1—C20 | 108.90 (13) | O2—C16—H16A | 110.2 |
C22—Si1—C20 | 111.28 (14) | C17—C16—H16A | 110.2 |
C16—O2—P1 | 121.38 (16) | O2—C16—H16B | 110.2 |
C18—O3—P1 | 122.23 (17) | C17—C16—H16B | 110.2 |
C10—N1—C1 | 120.3 (2) | H16A—C16—H16B | 108.5 |
C10—N1—H1B | 110.3 (19) | C16—C17—H17A | 109.5 |
C1—N1—H1B | 114 (2) | C16—C17—H17B | 109.5 |
N1—C1—C2 | 115.8 (2) | H17A—C17—H17B | 109.5 |
N1—C1—P1 | 106.11 (16) | C16—C17—H17C | 109.5 |
C2—C1—P1 | 111.53 (17) | H17A—C17—H17C | 109.5 |
N1—C1—H1A | 107.7 | H17B—C17—H17C | 109.5 |
C2—C1—H1A | 107.7 | O3—C18—C19 | 109.7 (2) |
P1—C1—H1A | 107.7 | O3—C18—H18A | 109.7 |
C3—C2—C7 | 118.8 (2) | C19—C18—H18A | 109.7 |
C3—C2—C1 | 121.3 (2) | O3—C18—H18B | 109.7 |
C7—C2—C1 | 119.9 (2) | C19—C18—H18B | 109.7 |
C2—C3—C4 | 120.7 (2) | H18A—C18—H18B | 108.2 |
C2—C3—H3A | 119.7 | C18—C19—H19A | 109.5 |
C4—C3—H3A | 119.7 | C18—C19—H19B | 109.5 |
C3—C4—C5 | 120.7 (2) | H19A—C19—H19B | 109.5 |
C3—C4—H4A | 119.7 | C18—C19—H19C | 109.5 |
C5—C4—H4A | 119.7 | H19A—C19—H19C | 109.5 |
C6—C5—C4 | 118.7 (2) | H19B—C19—H19C | 109.5 |
C6—C5—C8 | 120.5 (2) | Si1—C20—H20A | 109.5 |
C4—C5—C8 | 120.7 (2) | Si1—C20—H20B | 109.5 |
C7—C6—C5 | 120.1 (3) | H20A—C20—H20B | 109.5 |
C7—C6—H6A | 119.9 | Si1—C20—H20C | 109.5 |
C5—C6—H6A | 119.9 | H20A—C20—H20C | 109.5 |
C6—C7—C2 | 121.0 (2) | H20B—C20—H20C | 109.5 |
C6—C7—H7A | 119.5 | Si1—C21—H21A | 109.5 |
C2—C7—H7A | 119.5 | Si1—C21—H21B | 109.5 |
C9—C8—C5 | 178.7 (3) | H21A—C21—H21B | 109.5 |
C8—C9—Si1 | 176.4 (3) | Si1—C21—H21C | 109.5 |
C11—C10—C15 | 118.8 (2) | H21A—C21—H21C | 109.5 |
C11—C10—N1 | 122.9 (2) | H21B—C21—H21C | 109.5 |
C15—C10—N1 | 118.2 (2) | Si1—C22—H22A | 109.5 |
C10—C11—C12 | 120.6 (2) | Si1—C22—H22B | 109.5 |
C10—C11—H11A | 119.7 | H22A—C22—H22B | 109.5 |
C12—C11—H11A | 119.7 | Si1—C22—H22C | 109.5 |
C13—C12—C11 | 118.8 (3) | H22A—C22—H22C | 109.5 |
C13—C12—H12A | 120.6 | H22B—C22—H22C | 109.5 |
C11—C12—H12A | 120.6 | ||
O1—P1—O2—C16 | 28.0 (2) | C3—C4—C5—C6 | 1.2 (4) |
O3—P1—O2—C16 | 153.42 (19) | C3—C4—C5—C8 | −177.4 (2) |
C1—P1—O2—C16 | −96.1 (2) | C4—C5—C6—C7 | −0.4 (4) |
O1—P1—O3—C18 | −49.5 (2) | C8—C5—C6—C7 | 178.2 (3) |
O2—P1—O3—C18 | −174.78 (19) | C5—C6—C7—C2 | −0.7 (4) |
C1—P1—O3—C18 | 76.1 (2) | C3—C2—C7—C6 | 0.9 (4) |
C10—N1—C1—C2 | −68.2 (3) | C1—C2—C7—C6 | 177.7 (2) |
C10—N1—C1—P1 | 167.48 (18) | C1—N1—C10—C11 | −29.9 (3) |
O1—P1—C1—N1 | 44.5 (2) | C1—N1—C10—C15 | 153.3 (2) |
O3—P1—C1—N1 | −84.28 (18) | C15—C10—C11—C12 | 0.6 (4) |
O2—P1—C1—N1 | 171.83 (15) | N1—C10—C11—C12 | −176.1 (2) |
O1—P1—C1—C2 | −82.44 (19) | C10—C11—C12—C13 | −0.5 (4) |
O3—P1—C1—C2 | 148.76 (17) | C11—C12—C13—F1 | −179.0 (2) |
O2—P1—C1—C2 | 44.87 (19) | C11—C12—C13—C14 | 0.6 (4) |
N1—C1—C2—C3 | −44.1 (3) | C12—C13—C14—C15 | −0.9 (4) |
P1—C1—C2—C3 | 77.4 (3) | F1—C13—C14—C15 | 178.7 (2) |
N1—C1—C2—C7 | 139.1 (2) | C13—C14—C15—C10 | 1.0 (4) |
P1—C1—C2—C7 | −99.4 (2) | C11—C10—C15—C14 | −0.9 (4) |
C7—C2—C3—C4 | 0.0 (4) | N1—C10—C15—C14 | 176.0 (2) |
C1—C2—C3—C4 | −176.8 (2) | P1—O2—C16—C17 | 160.59 (18) |
C2—C3—C4—C5 | −1.1 (4) | P1—O3—C18—C19 | −109.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···O1i | 0.88 (3) | 2.21 (3) | 3.066 (3) | 165 (3) |
C15—H15A···O1i | 0.95 | 2.44 | 3.225 (3) | 140 |
C3—H3A···O1i | 0.95 | 2.71 | 3.629 (3) | 162 |
C6—H6A···F1ii | 0.95 | 2.67 | 3.424 (3) | 136 |
C14—H14A···F1iii | 0.95 | 2.76 | 3.442 (3) | 129 |
C21—H21B···Cg(C10–C15)iv | 0.98 | 2.83 | 3.785 (3) | 166 |
C21—H21C···Cg(C2–C7)iv | 0.98 | 2.95 | 3.713 (4) | 135 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+1, −z+2; (iii) −x, −y+2, −z+2; (iv) −x+2, −y+1, −z+2. |
C23H24NO3P | Z = 4 |
Mr = 393.40 | F(000) = 832 |
Triclinic, P1 | Dx = 1.266 Mg m−3 |
Hall symbol: -P 1 | Melting point: 418(1) K |
a = 11.3104 (10) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.5194 (10) Å | Cell parameters from 5680 reflections |
c = 17.8485 (16) Å | θ = 3–25° |
α = 82.703 (1)° | µ = 0.16 mm−1 |
β = 81.943 (1)° | T = 180 K |
γ = 64.035 (1)° | Block, pale brown |
V = 2064.5 (3) Å3 | 0.60 × 0.44 × 0.30 mm |
Siemens SMART 1K CCD area-detector diffractometer | 8309 independent reflections |
Radiation source: normal-focus sealed tube | 5727 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
ω scans | θmax = 26.5°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | h = −14→14 |
Tmin = 0.860, Tmax = 0.954 | k = −14→14 |
21384 measured reflections | l = −22→22 |
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)] = 0.075 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.156 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.04P)2 + 1.2P] where P = (Fo2 + 2Fc2)/3 |
8309 reflections | (Δ/σ)max = 0.001 |
517 parameters | Δρmax = 0.52 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
C23H24NO3P | γ = 64.035 (1)° |
Mr = 393.40 | V = 2064.5 (3) Å3 |
Triclinic, P1 | Z = 4 |
a = 11.3104 (10) Å | Mo Kα radiation |
b = 11.5194 (10) Å | µ = 0.16 mm−1 |
c = 17.8485 (16) Å | T = 180 K |
α = 82.703 (1)° | 0.60 × 0.44 × 0.30 mm |
β = 81.943 (1)° |
Siemens SMART 1K CCD area-detector diffractometer | 8309 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | 5727 reflections with I > 2σ(I) |
Tmin = 0.860, Tmax = 0.954 | Rint = 0.055 |
21384 measured reflections |
R[F2 > 2σ(F2)] = 0.075 | 0 restraints |
wR(F2) = 0.156 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Δρmax = 0.52 e Å−3 |
8309 reflections | Δρmin = −0.40 e Å−3 |
517 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
P1 | 0.29431 (8) | 0.30458 (7) | 0.20746 (4) | 0.0265 (2) | |
P2 | 0.26297 (8) | 0.79002 (7) | 0.69386 (4) | 0.0266 (2) | |
O1 | 0.43502 (19) | 0.22269 (19) | 0.18740 (11) | 0.0306 (5) | |
O2 | 0.19745 (19) | 0.27793 (19) | 0.16445 (11) | 0.0333 (5) | |
O3 | 0.2481 (2) | 0.45388 (19) | 0.19394 (12) | 0.0426 (6) | |
O4 | 0.40598 (19) | 0.73817 (19) | 0.67199 (11) | 0.0338 (5) | |
O5 | 0.1851 (2) | 0.7330 (2) | 0.65543 (11) | 0.0351 (5) | |
O6 | 0.18668 (19) | 0.94065 (18) | 0.67641 (11) | 0.0315 (5) | |
N1 | 0.3144 (3) | 0.3220 (2) | 0.35297 (13) | 0.0293 (6) | |
H1B | 0.396 (3) | 0.296 (3) | 0.3398 (16) | 0.026 (8)* | |
N2 | 0.2838 (3) | 0.8086 (2) | 0.83689 (13) | 0.0282 (6) | |
H2A | 0.366 (3) | 0.787 (2) | 0.8232 (15) | 0.014 (7)* | |
C1 | 0.2430 (3) | 0.2836 (3) | 0.30765 (15) | 0.0265 (7) | |
H1A | 0.1470 | 0.3425 | 0.3166 | 0.032* | |
C2 | 0.2592 (3) | 0.1437 (3) | 0.32391 (15) | 0.0265 (7) | |
C3 | 0.3808 (3) | 0.0455 (3) | 0.33859 (19) | 0.0413 (8) | |
H3A | 0.4523 | 0.0662 | 0.3424 | 0.050* | |
C4 | 0.4004 (3) | −0.0824 (3) | 0.3479 (2) | 0.0465 (9) | |
H4A | 0.4850 | −0.1485 | 0.3578 | 0.056* | |
C5 | 0.2972 (3) | −0.1151 (3) | 0.34285 (17) | 0.0366 (8) | |
C6 | 0.1738 (3) | −0.0153 (3) | 0.33018 (17) | 0.0356 (8) | |
H6A | 0.1011 | −0.0350 | 0.3285 | 0.043* | |
C7 | 0.1559 (3) | 0.1114 (3) | 0.32006 (16) | 0.0309 (7) | |
H7A | 0.0713 | 0.1779 | 0.3103 | 0.037* | |
C8 | 0.3179 (4) | −0.2489 (3) | 0.3500 (2) | 0.0464 (9) | |
C9 | 0.3353 (4) | −0.3579 (4) | 0.3536 (2) | 0.0611 (11) | |
H9A | 0.3493 | −0.4459 | 0.3565 | 0.073* | |
C10 | 0.2795 (3) | 0.3323 (3) | 0.43102 (15) | 0.0259 (6) | |
C11 | 0.1623 (3) | 0.3339 (3) | 0.46709 (15) | 0.0273 (7) | |
H11A | 0.1041 | 0.3212 | 0.4389 | 0.033* | |
C12 | 0.1277 (3) | 0.3541 (3) | 0.54528 (15) | 0.0266 (7) | |
C13 | 0.2143 (3) | 0.3734 (3) | 0.58760 (16) | 0.0277 (7) | |
C14 | 0.3351 (3) | 0.3692 (3) | 0.54937 (17) | 0.0318 (7) | |
H14A | 0.3948 | 0.3809 | 0.5768 | 0.038* | |
C15 | 0.3667 (3) | 0.3488 (3) | 0.47421 (16) | 0.0293 (7) | |
H15A | 0.4485 | 0.3455 | 0.4502 | 0.035* | |
C16 | 0.2390 (3) | 0.1607 (3) | 0.12558 (18) | 0.0430 (8) | |
H16A | 0.1648 | 0.1359 | 0.1293 | 0.052* | |
H16B | 0.3128 | 0.0891 | 0.1503 | 0.052* | |
C17 | 0.2825 (4) | 0.1814 (4) | 0.0436 (2) | 0.0644 (12) | |
H17A | 0.3021 | 0.1044 | 0.0172 | 0.097* | |
H17B | 0.3619 | 0.1966 | 0.0398 | 0.097* | |
H17C | 0.2118 | 0.2567 | 0.0201 | 0.097* | |
C18 | 0.2302 (5) | 0.5244 (4) | 0.1202 (2) | 0.0677 (13) | |
H18A | 0.1666 | 0.5063 | 0.0964 | 0.081* | |
H18B | 0.1879 | 0.6179 | 0.1284 | 0.081* | |
C19 | 0.3414 (5) | 0.5017 (4) | 0.0670 (3) | 0.0851 (16) | |
H19A | 0.3132 | 0.5543 | 0.0197 | 0.128* | |
H19B | 0.3848 | 0.4098 | 0.0571 | 0.128* | |
H19C | 0.4034 | 0.5251 | 0.0874 | 0.128* | |
C20 | 0.0085 (3) | 0.3557 (3) | 0.58369 (16) | 0.0317 (7) | |
H20A | −0.0506 | 0.3426 | 0.5565 | 0.038* | |
C21 | −0.0228 (3) | 0.3760 (3) | 0.65947 (17) | 0.0352 (8) | |
H21A | −0.1030 | 0.3763 | 0.6842 | 0.042* | |
C22 | 0.0623 (3) | 0.3961 (3) | 0.70062 (17) | 0.0389 (8) | |
H22A | 0.0395 | 0.4102 | 0.7530 | 0.047* | |
C23 | 0.1778 (3) | 0.3956 (3) | 0.66576 (17) | 0.0363 (8) | |
H23A | 0.2345 | 0.4102 | 0.6941 | 0.044* | |
C24 | 0.2218 (3) | 0.7548 (3) | 0.79392 (15) | 0.0260 (6) | |
H24A | 0.1239 | 0.8019 | 0.8052 | 0.031* | |
C25 | 0.2608 (3) | 0.6102 (3) | 0.81254 (15) | 0.0267 (7) | |
C26 | 0.3922 (3) | 0.5224 (3) | 0.80202 (18) | 0.0361 (8) | |
H26A | 0.4575 | 0.5534 | 0.7856 | 0.043* | |
C27 | 0.4301 (3) | 0.3907 (3) | 0.81496 (18) | 0.0403 (8) | |
H27A | 0.5206 | 0.3323 | 0.8067 | 0.048* | |
C28 | 0.3360 (3) | 0.3430 (3) | 0.84007 (16) | 0.0336 (7) | |
C29 | 0.2049 (3) | 0.4309 (3) | 0.85428 (16) | 0.0343 (7) | |
H29A | 0.1403 | 0.4004 | 0.8742 | 0.041* | |
C30 | 0.1675 (3) | 0.5631 (3) | 0.83956 (16) | 0.0305 (7) | |
H30A | 0.0772 | 0.6220 | 0.8481 | 0.037* | |
C31 | 0.3754 (3) | 0.2050 (3) | 0.84541 (18) | 0.0401 (8) | |
C32 | 0.4093 (4) | 0.0920 (4) | 0.8444 (2) | 0.0509 (10) | |
H32A | 0.4364 | 0.0016 | 0.8436 | 0.061* | |
C33 | 0.2505 (3) | 0.8181 (3) | 0.91559 (15) | 0.0253 (6) | |
C34 | 0.1325 (3) | 0.8228 (3) | 0.95176 (16) | 0.0275 (7) | |
H34A | 0.0719 | 0.8140 | 0.9236 | 0.033* | |
C35 | 0.1003 (3) | 0.8405 (3) | 1.03078 (16) | 0.0278 (7) | |
C36 | 0.1910 (3) | 0.8517 (3) | 1.07301 (16) | 0.0292 (7) | |
C37 | 0.3123 (3) | 0.8446 (3) | 1.03464 (16) | 0.0316 (7) | |
H37A | 0.3747 | 0.8513 | 1.0622 | 0.038* | |
C38 | 0.3409 (3) | 0.8283 (3) | 0.95844 (16) | 0.0298 (7) | |
H38A | 0.4229 | 0.8237 | 0.9341 | 0.036* | |
C39 | 0.2062 (4) | 0.7183 (4) | 0.57355 (19) | 0.0502 (10) | |
H39A | 0.1963 | 0.6404 | 0.5639 | 0.060* | |
H39B | 0.2975 | 0.7054 | 0.5549 | 0.060* | |
C40 | 0.1117 (4) | 0.8328 (4) | 0.53111 (19) | 0.0555 (11) | |
H40A | 0.1303 | 0.8202 | 0.4767 | 0.083* | |
H40B | 0.1209 | 0.9102 | 0.5407 | 0.083* | |
H40C | 0.0214 | 0.8437 | 0.5479 | 0.083* | |
C41 | 0.2558 (3) | 1.0239 (3) | 0.65979 (19) | 0.0385 (8) | |
H41A | 0.3288 | 0.9936 | 0.6927 | 0.046* | |
H41B | 0.1939 | 1.1135 | 0.6715 | 0.046* | |
C42 | 0.3110 (4) | 1.0236 (3) | 0.57795 (19) | 0.0455 (9) | |
H42A | 0.3509 | 1.0849 | 0.5680 | 0.068* | |
H42B | 0.2396 | 1.0491 | 0.5452 | 0.068* | |
H42C | 0.3782 | 0.9365 | 0.5674 | 0.068* | |
C43 | −0.0209 (3) | 0.8466 (3) | 1.06854 (17) | 0.0321 (7) | |
H43A | −0.0830 | 0.8400 | 1.0406 | 0.039* | |
C44 | −0.0497 (3) | 0.8619 (3) | 1.14493 (18) | 0.0366 (8) | |
H44A | −0.1312 | 0.8652 | 1.1694 | 0.044* | |
C45 | 0.0402 (3) | 0.8727 (3) | 1.18718 (18) | 0.0393 (8) | |
H45A | 0.0194 | 0.8832 | 1.2401 | 0.047* | |
C46 | 0.1581 (3) | 0.8681 (3) | 1.15238 (17) | 0.0356 (8) | |
H46A | 0.2183 | 0.8760 | 1.1813 | 0.043* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0297 (4) | 0.0276 (4) | 0.0190 (4) | −0.0109 (3) | 0.0033 (3) | −0.0014 (3) |
P2 | 0.0252 (4) | 0.0309 (4) | 0.0195 (4) | −0.0093 (3) | −0.0003 (3) | 0.0005 (3) |
O1 | 0.0302 (12) | 0.0368 (12) | 0.0249 (11) | −0.0159 (10) | 0.0050 (9) | −0.0055 (9) |
O2 | 0.0295 (12) | 0.0405 (12) | 0.0257 (11) | −0.0115 (10) | −0.0023 (9) | −0.0011 (9) |
O3 | 0.0610 (16) | 0.0293 (12) | 0.0277 (12) | −0.0143 (11) | 0.0085 (11) | −0.0008 (9) |
O4 | 0.0274 (12) | 0.0421 (12) | 0.0260 (11) | −0.0110 (10) | 0.0013 (9) | −0.0005 (9) |
O5 | 0.0405 (13) | 0.0422 (13) | 0.0260 (11) | −0.0205 (11) | −0.0080 (10) | 0.0016 (9) |
O6 | 0.0285 (12) | 0.0333 (11) | 0.0290 (11) | −0.0117 (10) | 0.0025 (9) | −0.0002 (9) |
N1 | 0.0269 (15) | 0.0406 (15) | 0.0209 (13) | −0.0166 (13) | 0.0059 (11) | −0.0048 (11) |
N2 | 0.0246 (15) | 0.0374 (15) | 0.0214 (13) | −0.0141 (12) | 0.0045 (11) | −0.0027 (11) |
C1 | 0.0266 (16) | 0.0303 (16) | 0.0184 (14) | −0.0092 (13) | 0.0022 (12) | −0.0031 (12) |
C2 | 0.0267 (16) | 0.0340 (16) | 0.0161 (14) | −0.0125 (14) | 0.0043 (12) | −0.0016 (12) |
C3 | 0.0302 (19) | 0.041 (2) | 0.054 (2) | −0.0187 (16) | −0.0088 (16) | 0.0081 (16) |
C4 | 0.0326 (19) | 0.0380 (19) | 0.061 (2) | −0.0108 (16) | −0.0095 (17) | 0.0125 (17) |
C5 | 0.048 (2) | 0.0372 (18) | 0.0255 (16) | −0.0217 (17) | 0.0013 (15) | 0.0029 (14) |
C6 | 0.0358 (19) | 0.046 (2) | 0.0297 (17) | −0.0237 (16) | 0.0013 (14) | −0.0030 (14) |
C7 | 0.0280 (17) | 0.0372 (18) | 0.0254 (16) | −0.0130 (14) | 0.0002 (13) | −0.0025 (13) |
C8 | 0.053 (2) | 0.046 (2) | 0.041 (2) | −0.0255 (19) | 0.0042 (17) | 0.0014 (16) |
C9 | 0.074 (3) | 0.043 (2) | 0.065 (3) | −0.027 (2) | 0.002 (2) | 0.000 (2) |
C10 | 0.0285 (16) | 0.0235 (15) | 0.0217 (15) | −0.0086 (13) | 0.0007 (13) | −0.0009 (11) |
C11 | 0.0320 (17) | 0.0298 (16) | 0.0211 (15) | −0.0142 (14) | −0.0010 (13) | −0.0033 (12) |
C12 | 0.0286 (16) | 0.0241 (15) | 0.0225 (15) | −0.0084 (13) | 0.0027 (13) | −0.0017 (12) |
C13 | 0.0319 (17) | 0.0228 (15) | 0.0242 (15) | −0.0087 (13) | −0.0029 (13) | 0.0011 (12) |
C14 | 0.0319 (18) | 0.0334 (17) | 0.0302 (17) | −0.0131 (14) | −0.0077 (14) | 0.0000 (13) |
C15 | 0.0284 (17) | 0.0317 (16) | 0.0272 (16) | −0.0135 (14) | 0.0005 (13) | −0.0005 (13) |
C16 | 0.043 (2) | 0.055 (2) | 0.0374 (19) | −0.0249 (18) | −0.0068 (16) | −0.0075 (16) |
C17 | 0.082 (3) | 0.093 (3) | 0.040 (2) | −0.056 (3) | 0.004 (2) | −0.025 (2) |
C18 | 0.096 (3) | 0.038 (2) | 0.048 (2) | −0.019 (2) | 0.011 (2) | 0.0138 (18) |
C19 | 0.108 (4) | 0.052 (3) | 0.061 (3) | −0.017 (3) | 0.029 (3) | 0.009 (2) |
C20 | 0.0342 (18) | 0.0345 (17) | 0.0260 (16) | −0.0150 (14) | 0.0002 (14) | −0.0033 (13) |
C21 | 0.0372 (19) | 0.0385 (18) | 0.0253 (16) | −0.0155 (15) | 0.0083 (14) | −0.0019 (13) |
C22 | 0.045 (2) | 0.045 (2) | 0.0201 (16) | −0.0138 (17) | 0.0030 (15) | −0.0049 (14) |
C23 | 0.042 (2) | 0.0417 (19) | 0.0230 (16) | −0.0151 (16) | −0.0053 (14) | −0.0028 (14) |
C24 | 0.0236 (16) | 0.0339 (16) | 0.0190 (14) | −0.0120 (13) | 0.0015 (12) | −0.0018 (12) |
C25 | 0.0283 (17) | 0.0343 (16) | 0.0172 (14) | −0.0128 (14) | −0.0043 (12) | −0.0005 (12) |
C26 | 0.0275 (17) | 0.0385 (18) | 0.0398 (19) | −0.0146 (15) | −0.0011 (14) | 0.0056 (15) |
C27 | 0.0327 (19) | 0.0366 (19) | 0.042 (2) | −0.0072 (15) | −0.0047 (15) | 0.0043 (15) |
C28 | 0.041 (2) | 0.0361 (18) | 0.0221 (16) | −0.0149 (16) | −0.0061 (14) | −0.0004 (13) |
C29 | 0.040 (2) | 0.0438 (19) | 0.0256 (16) | −0.0243 (16) | −0.0025 (14) | −0.0023 (14) |
C30 | 0.0309 (17) | 0.0376 (18) | 0.0212 (15) | −0.0136 (14) | 0.0010 (13) | −0.0040 (13) |
C31 | 0.049 (2) | 0.040 (2) | 0.0297 (17) | −0.0185 (17) | −0.0054 (15) | 0.0011 (15) |
C32 | 0.064 (3) | 0.037 (2) | 0.052 (2) | −0.0228 (19) | −0.0063 (19) | 0.0014 (17) |
C33 | 0.0292 (16) | 0.0220 (15) | 0.0215 (14) | −0.0093 (13) | 0.0003 (12) | 0.0001 (11) |
C34 | 0.0278 (16) | 0.0296 (16) | 0.0235 (15) | −0.0115 (13) | −0.0009 (13) | −0.0012 (12) |
C35 | 0.0292 (17) | 0.0232 (15) | 0.0266 (16) | −0.0087 (13) | 0.0018 (13) | −0.0010 (12) |
C36 | 0.0362 (18) | 0.0260 (16) | 0.0231 (15) | −0.0123 (14) | 0.0020 (13) | −0.0030 (12) |
C37 | 0.0323 (18) | 0.0405 (18) | 0.0272 (16) | −0.0202 (15) | −0.0023 (14) | −0.0039 (14) |
C38 | 0.0271 (17) | 0.0341 (17) | 0.0262 (16) | −0.0131 (14) | 0.0022 (13) | −0.0007 (13) |
C39 | 0.048 (2) | 0.061 (2) | 0.039 (2) | −0.0152 (19) | −0.0048 (17) | −0.0259 (18) |
C40 | 0.090 (3) | 0.062 (2) | 0.0254 (18) | −0.042 (2) | −0.0118 (19) | 0.0013 (17) |
C41 | 0.0383 (19) | 0.0316 (17) | 0.048 (2) | −0.0176 (15) | −0.0020 (16) | −0.0039 (15) |
C42 | 0.052 (2) | 0.0384 (19) | 0.044 (2) | −0.0219 (17) | 0.0037 (17) | 0.0043 (16) |
C43 | 0.0297 (17) | 0.0334 (17) | 0.0292 (17) | −0.0113 (14) | 0.0032 (13) | −0.0036 (13) |
C44 | 0.0328 (18) | 0.0375 (18) | 0.0341 (18) | −0.0134 (15) | 0.0099 (15) | −0.0047 (14) |
C45 | 0.048 (2) | 0.0404 (19) | 0.0248 (16) | −0.0174 (17) | 0.0092 (15) | −0.0073 (14) |
C46 | 0.046 (2) | 0.0398 (18) | 0.0245 (16) | −0.0206 (16) | −0.0028 (15) | −0.0052 (14) |
P1—O1 | 1.471 (2) | C19—H19B | 0.9800 |
P1—O3 | 1.559 (2) | C19—H19C | 0.9800 |
P1—O2 | 1.573 (2) | C20—C21 | 1.372 (4) |
P1—C1 | 1.821 (3) | C20—H20A | 0.9500 |
P2—O4 | 1.470 (2) | C21—C22 | 1.399 (4) |
P2—O5 | 1.571 (2) | C21—H21A | 0.9500 |
P2—O6 | 1.575 (2) | C22—C23 | 1.364 (4) |
P2—C24 | 1.822 (3) | C22—H22A | 0.9500 |
O2—C16 | 1.455 (4) | C23—H23A | 0.9500 |
O3—C18 | 1.447 (4) | C24—C25 | 1.528 (4) |
O5—C39 | 1.467 (4) | C24—H24A | 1.0000 |
O6—C41 | 1.463 (4) | C25—C26 | 1.385 (4) |
N1—C10 | 1.399 (3) | C25—C30 | 1.390 (4) |
N1—C1 | 1.445 (4) | C26—C27 | 1.381 (4) |
N1—H1B | 0.85 (3) | C26—H26A | 0.9500 |
N2—C33 | 1.408 (3) | C27—C28 | 1.398 (4) |
N2—C24 | 1.455 (4) | C27—H27A | 0.9500 |
N2—H2A | 0.86 (3) | C28—C29 | 1.391 (4) |
C1—C2 | 1.534 (4) | C28—C31 | 1.444 (4) |
C1—H1A | 1.0000 | C29—C30 | 1.390 (4) |
C2—C3 | 1.380 (4) | C29—H29A | 0.9500 |
C2—C7 | 1.385 (4) | C30—H30A | 0.9500 |
C3—C4 | 1.382 (4) | C31—C32 | 1.187 (4) |
C3—H3A | 0.9500 | C32—H32A | 0.9500 |
C4—C5 | 1.391 (5) | C33—C34 | 1.380 (4) |
C4—H4A | 0.9500 | C33—C38 | 1.411 (4) |
C5—C6 | 1.392 (4) | C34—C35 | 1.424 (4) |
C5—C8 | 1.446 (5) | C34—H34A | 0.9500 |
C6—C7 | 1.374 (4) | C35—C36 | 1.412 (4) |
C6—H6A | 0.9500 | C35—C43 | 1.416 (4) |
C7—H7A | 0.9500 | C36—C37 | 1.418 (4) |
C8—C9 | 1.178 (5) | C36—C46 | 1.428 (4) |
C9—H9A | 0.9500 | C37—C38 | 1.371 (4) |
C10—C11 | 1.384 (4) | C37—H37A | 0.9500 |
C10—C15 | 1.420 (4) | C38—H38A | 0.9500 |
C11—C12 | 1.416 (4) | C39—C40 | 1.481 (5) |
C11—H11A | 0.9500 | C39—H39A | 0.9900 |
C12—C20 | 1.418 (4) | C39—H39B | 0.9900 |
C12—C13 | 1.421 (4) | C40—H40A | 0.9800 |
C13—C23 | 1.421 (4) | C40—H40B | 0.9800 |
C13—C14 | 1.423 (4) | C40—H40C | 0.9800 |
C14—C15 | 1.362 (4) | C41—C42 | 1.505 (4) |
C14—H14A | 0.9500 | C41—H41A | 0.9900 |
C15—H15A | 0.9500 | C41—H41B | 0.9900 |
C16—C17 | 1.501 (5) | C42—H42A | 0.9800 |
C16—H16A | 0.9900 | C42—H42B | 0.9800 |
C16—H16B | 0.9900 | C42—H42C | 0.9800 |
C17—H17A | 0.9800 | C43—C44 | 1.372 (4) |
C17—H17B | 0.9800 | C43—H43A | 0.9500 |
C17—H17C | 0.9800 | C44—C45 | 1.403 (5) |
C18—C19 | 1.410 (5) | C44—H44A | 0.9500 |
C18—H18A | 0.9900 | C45—C46 | 1.372 (4) |
C18—H18B | 0.9900 | C45—H45A | 0.9500 |
C19—H19A | 0.9800 | C46—H46A | 0.9500 |
O1—P1—O3 | 116.72 (12) | C21—C20—H20A | 119.5 |
O1—P1—O2 | 114.27 (11) | C12—C20—H20A | 119.5 |
O3—P1—O2 | 103.90 (12) | C20—C21—C22 | 120.6 (3) |
O1—P1—C1 | 112.85 (13) | C20—C21—H21A | 119.7 |
O3—P1—C1 | 103.00 (12) | C22—C21—H21A | 119.7 |
O2—P1—C1 | 104.72 (12) | C23—C22—C21 | 120.2 (3) |
O4—P2—O5 | 116.27 (12) | C23—C22—H22A | 119.9 |
O4—P2—O6 | 114.01 (12) | C21—C22—H22A | 119.9 |
O5—P2—O6 | 103.82 (11) | C22—C23—C13 | 120.8 (3) |
O4—P2—C24 | 113.29 (13) | C22—C23—H23A | 119.6 |
O5—P2—C24 | 101.00 (12) | C13—C23—H23A | 119.6 |
O6—P2—C24 | 107.13 (12) | N2—C24—C25 | 114.3 (2) |
C16—O2—P1 | 122.56 (19) | N2—C24—P2 | 106.79 (18) |
C18—O3—P1 | 124.4 (2) | C25—C24—P2 | 111.47 (19) |
C39—O5—P2 | 121.2 (2) | N2—C24—H24A | 108.0 |
C41—O6—P2 | 121.75 (19) | C25—C24—H24A | 108.0 |
C10—N1—C1 | 120.6 (2) | P2—C24—H24A | 108.0 |
C10—N1—H1B | 115 (2) | C26—C25—C30 | 118.4 (3) |
C1—N1—H1B | 116 (2) | C26—C25—C24 | 119.8 (3) |
C33—N2—C24 | 120.2 (2) | C30—C25—C24 | 121.7 (3) |
C33—N2—H2A | 113.8 (18) | C27—C26—C25 | 121.3 (3) |
C24—N2—H2A | 114.6 (18) | C27—C26—H26A | 119.4 |
N1—C1—C2 | 115.7 (2) | C25—C26—H26A | 119.4 |
N1—C1—P1 | 109.68 (19) | C26—C27—C28 | 120.4 (3) |
C2—C1—P1 | 107.49 (18) | C26—C27—H27A | 119.8 |
N1—C1—H1A | 107.9 | C28—C27—H27A | 119.8 |
C2—C1—H1A | 107.9 | C29—C28—C27 | 118.5 (3) |
P1—C1—H1A | 107.9 | C29—C28—C31 | 121.9 (3) |
C3—C2—C7 | 118.4 (3) | C27—C28—C31 | 119.4 (3) |
C3—C2—C1 | 119.9 (3) | C30—C29—C28 | 120.5 (3) |
C7—C2—C1 | 121.5 (3) | C30—C29—H29A | 119.7 |
C2—C3—C4 | 121.1 (3) | C28—C29—H29A | 119.7 |
C2—C3—H3A | 119.5 | C25—C30—C29 | 120.8 (3) |
C4—C3—H3A | 119.5 | C25—C30—H30A | 119.6 |
C3—C4—C5 | 120.5 (3) | C29—C30—H30A | 119.6 |
C3—C4—H4A | 119.7 | C32—C31—C28 | 175.4 (4) |
C5—C4—H4A | 119.7 | C31—C32—H32A | 180.0 |
C4—C5—C6 | 118.1 (3) | C34—C33—N2 | 123.2 (3) |
C4—C5—C8 | 120.9 (3) | C34—C33—C38 | 119.0 (3) |
C6—C5—C8 | 121.1 (3) | N2—C33—C38 | 117.7 (3) |
C7—C6—C5 | 120.9 (3) | C33—C34—C35 | 120.9 (3) |
C7—C6—H6A | 119.6 | C33—C34—H34A | 119.6 |
C5—C6—H6A | 119.6 | C35—C34—H34A | 119.6 |
C6—C7—C2 | 121.0 (3) | C36—C35—C43 | 118.8 (3) |
C6—C7—H7A | 119.5 | C36—C35—C34 | 119.6 (3) |
C2—C7—H7A | 119.5 | C43—C35—C34 | 121.5 (3) |
C9—C8—C5 | 178.0 (4) | C35—C36—C37 | 118.3 (3) |
C8—C9—H9A | 180.0 | C35—C36—C46 | 119.1 (3) |
C11—C10—N1 | 123.5 (3) | C37—C36—C46 | 122.6 (3) |
C11—C10—C15 | 118.8 (3) | C38—C37—C36 | 121.1 (3) |
N1—C10—C15 | 117.6 (3) | C38—C37—H37A | 119.4 |
C10—C11—C12 | 121.1 (3) | C36—C37—H37A | 119.4 |
C10—C11—H11A | 119.5 | C37—C38—C33 | 121.1 (3) |
C12—C11—H11A | 119.5 | C37—C38—H38A | 119.5 |
C11—C12—C20 | 122.2 (3) | C33—C38—H38A | 119.5 |
C11—C12—C13 | 119.7 (3) | O5—C39—C40 | 111.9 (3) |
C20—C12—C13 | 118.1 (3) | O5—C39—H39A | 109.2 |
C23—C13—C12 | 119.3 (3) | C40—C39—H39A | 109.2 |
C23—C13—C14 | 122.6 (3) | O5—C39—H39B | 109.2 |
C12—C13—C14 | 118.1 (3) | C40—C39—H39B | 109.2 |
C15—C14—C13 | 121.2 (3) | H39A—C39—H39B | 107.9 |
C15—C14—H14A | 119.4 | C39—C40—H40A | 109.5 |
C13—C14—H14A | 119.4 | C39—C40—H40B | 109.5 |
C14—C15—C10 | 121.2 (3) | H40A—C40—H40B | 109.5 |
C14—C15—H15A | 119.4 | C39—C40—H40C | 109.5 |
C10—C15—H15A | 119.4 | H40A—C40—H40C | 109.5 |
O2—C16—C17 | 110.6 (3) | H40B—C40—H40C | 109.5 |
O2—C16—H16A | 109.5 | O6—C41—C42 | 111.7 (3) |
C17—C16—H16A | 109.5 | O6—C41—H41A | 109.3 |
O2—C16—H16B | 109.5 | C42—C41—H41A | 109.3 |
C17—C16—H16B | 109.5 | O6—C41—H41B | 109.3 |
H16A—C16—H16B | 108.1 | C42—C41—H41B | 109.3 |
C16—C17—H17A | 109.5 | H41A—C41—H41B | 107.9 |
C16—C17—H17B | 109.5 | C41—C42—H42A | 109.5 |
H17A—C17—H17B | 109.5 | C41—C42—H42B | 109.5 |
C16—C17—H17C | 109.5 | H42A—C42—H42B | 109.5 |
H17A—C17—H17C | 109.5 | C41—C42—H42C | 109.5 |
H17B—C17—H17C | 109.5 | H42A—C42—H42C | 109.5 |
C19—C18—O3 | 119.1 (4) | H42B—C42—H42C | 109.5 |
C19—C18—H18A | 107.5 | C44—C43—C35 | 120.9 (3) |
O3—C18—H18A | 107.5 | C44—C43—H43A | 119.6 |
C19—C18—H18B | 107.5 | C35—C43—H43A | 119.6 |
O3—C18—H18B | 107.5 | C43—C44—C45 | 120.5 (3) |
H18A—C18—H18B | 107.0 | C43—C44—H44A | 119.7 |
C18—C19—H19A | 109.5 | C45—C44—H44A | 119.7 |
C18—C19—H19B | 109.5 | C46—C45—C44 | 120.2 (3) |
H19A—C19—H19B | 109.5 | C46—C45—H45A | 119.9 |
C18—C19—H19C | 109.5 | C44—C45—H45A | 119.9 |
H19A—C19—H19C | 109.5 | C45—C46—C36 | 120.5 (3) |
H19B—C19—H19C | 109.5 | C45—C46—H46A | 119.8 |
C21—C20—C12 | 121.0 (3) | C36—C46—H46A | 119.8 |
O1—P1—O2—C16 | 16.7 (3) | C13—C12—C20—C21 | 0.3 (4) |
O3—P1—O2—C16 | 145.0 (2) | C12—C20—C21—C22 | 0.3 (5) |
C1—P1—O2—C16 | −107.3 (2) | C20—C21—C22—C23 | −0.1 (5) |
O1—P1—O3—C18 | 74.8 (3) | C21—C22—C23—C13 | −0.6 (5) |
O2—P1—O3—C18 | −51.9 (3) | C12—C13—C23—C22 | 1.2 (4) |
C1—P1—O3—C18 | −161.0 (3) | C14—C13—C23—C22 | −178.6 (3) |
O4—P2—O5—C39 | −46.2 (3) | C33—N2—C24—C25 | −67.9 (3) |
O6—P2—O5—C39 | 79.9 (2) | C33—N2—C24—P2 | 168.3 (2) |
C24—P2—O5—C39 | −169.2 (2) | O4—P2—C24—N2 | 57.5 (2) |
O4—P2—O6—C41 | −15.7 (3) | O5—P2—C24—N2 | −177.47 (18) |
O5—P2—O6—C41 | −143.2 (2) | O6—P2—C24—N2 | −69.1 (2) |
C24—P2—O6—C41 | 110.5 (2) | O4—P2—C24—C25 | −68.0 (2) |
C10—N1—C1—C2 | −67.3 (3) | O5—P2—C24—C25 | 57.0 (2) |
C10—N1—C1—P1 | 170.9 (2) | O6—P2—C24—C25 | 165.37 (19) |
O1—P1—C1—N1 | 62.4 (2) | N2—C24—C25—C26 | −59.7 (3) |
O3—P1—C1—N1 | −64.3 (2) | P2—C24—C25—C26 | 61.6 (3) |
O2—P1—C1—N1 | −172.68 (19) | N2—C24—C25—C30 | 120.8 (3) |
O1—P1—C1—C2 | −64.1 (2) | P2—C24—C25—C30 | −118.0 (3) |
O3—P1—C1—C2 | 169.18 (19) | C30—C25—C26—C27 | 2.6 (4) |
O2—P1—C1—C2 | 60.8 (2) | C24—C25—C26—C27 | −177.0 (3) |
N1—C1—C2—C3 | −39.3 (4) | C25—C26—C27—C28 | −0.8 (5) |
P1—C1—C2—C3 | 83.6 (3) | C26—C27—C28—C29 | −2.3 (5) |
N1—C1—C2—C7 | 144.4 (3) | C26—C27—C28—C31 | 173.4 (3) |
P1—C1—C2—C7 | −92.7 (3) | C27—C28—C29—C30 | 3.7 (4) |
C7—C2—C3—C4 | 1.2 (5) | C31—C28—C29—C30 | −171.9 (3) |
C1—C2—C3—C4 | −175.2 (3) | C26—C25—C30—C29 | −1.2 (4) |
C2—C3—C4—C5 | −0.2 (5) | C24—C25—C30—C29 | 178.3 (3) |
C3—C4—C5—C6 | −1.6 (5) | C28—C29—C30—C25 | −1.9 (4) |
C3—C4—C5—C8 | 177.9 (3) | C24—N2—C33—C34 | −23.5 (4) |
C4—C5—C6—C7 | 2.5 (5) | C24—N2—C33—C38 | 159.0 (3) |
C8—C5—C6—C7 | −177.1 (3) | N2—C33—C34—C35 | −176.1 (2) |
C5—C6—C7—C2 | −1.5 (5) | C38—C33—C34—C35 | 1.4 (4) |
C3—C2—C7—C6 | −0.3 (4) | C33—C34—C35—C36 | −0.9 (4) |
C1—C2—C7—C6 | 176.0 (3) | C33—C34—C35—C43 | 179.4 (3) |
C1—N1—C10—C11 | −13.9 (4) | C43—C35—C36—C37 | 179.6 (3) |
C1—N1—C10—C15 | 169.6 (2) | C34—C35—C36—C37 | −0.1 (4) |
N1—C10—C11—C12 | −175.3 (3) | C43—C35—C36—C46 | 0.3 (4) |
C15—C10—C11—C12 | 1.2 (4) | C34—C35—C36—C46 | −179.4 (3) |
C10—C11—C12—C20 | −179.8 (3) | C35—C36—C37—C38 | 0.4 (4) |
C10—C11—C12—C13 | 0.2 (4) | C46—C36—C37—C38 | 179.7 (3) |
C11—C12—C13—C23 | 179.0 (3) | C36—C37—C38—C33 | 0.1 (5) |
C20—C12—C13—C23 | −1.0 (4) | C34—C33—C38—C37 | −1.1 (4) |
C11—C12—C13—C14 | −1.1 (4) | N2—C33—C38—C37 | 176.6 (3) |
C20—C12—C13—C14 | 178.8 (3) | P2—O5—C39—C40 | −92.7 (3) |
C23—C13—C14—C15 | −179.5 (3) | P2—O6—C41—C42 | 82.4 (3) |
C12—C13—C14—C15 | 0.7 (4) | C36—C35—C43—C44 | −0.6 (4) |
C13—C14—C15—C10 | 0.7 (4) | C34—C35—C43—C44 | 179.1 (3) |
C11—C10—C15—C14 | −1.7 (4) | C35—C43—C44—C45 | 0.4 (5) |
N1—C10—C15—C14 | 175.0 (3) | C43—C44—C45—C46 | 0.0 (5) |
P1—O2—C16—C17 | −92.8 (3) | C44—C45—C46—C36 | −0.3 (5) |
P1—O3—C18—C19 | −65.9 (5) | C35—C36—C46—C45 | 0.2 (4) |
C11—C12—C20—C21 | −179.8 (3) | C37—C36—C46—C45 | −179.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···O4i | 0.85 (3) | 2.08 (3) | 2.906 (3) | 166 (3) |
N2—H2A···O1i | 0.86 (3) | 2.19 (3) | 3.013 (3) | 162 (2) |
C15—H15A···O4i | 0.95 | 2.56 | 3.309 (3) | 136 |
C32—H32A···O1ii | 0.95 | 2.44 | 3.349 (4) | 161 |
C38—H38A···O1i | 0.95 | 2.48 | 3.283 (3) | 143 |
C7—H7A···O5iii | 0.95 | 2.63 | 3.457 (4) | 146 |
C18—H18B···Cg(C35/C36/C43–C46)iv | 0.99 | 2.48 | 3.439 (4) | 163 |
C19—H19A···Cg(C33–C38)iv | 0.98 | 2.92 | 3.591 (5) | 127 |
C23—H23A···Cg(C25–C30) | 0.95 | 2.86 | 3.735 (4) | 153 |
C41—H41B···Cg(C12/C13/C20–C23)v | 0.99 | 2.78 | 3.649 (3) | 147 |
C42—H42A···Cg(C10–C15)v | 0.98 | 2.88 | 3.609 (3) | 132 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) −x, −y+1, −z+1; (iv) x, y, z−1; (v) x, y+1, z. |
Experimental details
(I) | (II) | (III) | (IV) | |
Crystal data | ||||
Chemical formula | C19H21BrNO3P | C23H31ClNO3PSi | C22H29FNO3PSi | C23H24NO3P |
Mr | 422.25 | 464.00 | 433.52 | 393.40 |
Crystal system, space group | Monoclinic, P21/n | Monoclinic, I2/a | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 186 | 183 | 184 | 180 |
a, b, c (Å) | 10.9339 (7), 16.5179 (11), 11.1325 (7) | 17.3791 (16), 14.7131 (13), 20.019 (3) | 8.9633 (7), 11.1726 (9), 12.6997 (10) | 11.3104 (10), 11.5194 (10), 17.8485 (16) |
α, β, γ (°) | 90, 104.114 (1), 90 | 90, 90.464 (1), 90 | 69.980 (1), 87.263 (1), 73.667 (1) | 82.703 (1), 81.943 (1), 64.035 (1) |
V (Å3) | 1949.9 (2) | 5118.6 (10) | 1145.06 (16) | 2064.5 (3) |
Z | 4 | 8 | 2 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 2.21 | 0.28 | 0.20 | 0.16 |
Crystal size (mm) | 0.60 × 0.60 × 0.50 | 0.38 × 0.36 × 0.34 | 0.40 × 0.40 × 0.30 | 0.60 × 0.44 × 0.30 |
Data collection | ||||
Diffractometer | Siemens SMART 1K CCD area-detector diffractometer | Siemens SMART 1K CCD area-detector diffractometer | Siemens SMART 1K CCD area-detector diffractometer | Siemens SMART 1K CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2000) | Multi-scan (SADABS; Sheldrick, 2000) | Multi-scan (SADABS; Sheldrick, 2000) | Multi-scan (SADABS; Sheldrick, 2000) |
Tmin, Tmax | 0.284, 0.332 | 0.790, 0.909 | 0.852, 0.941 | 0.860, 0.954 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 22735, 4762, 4104 | 24553, 5021, 3655 | 12221, 4782, 3504 | 21384, 8309, 5727 |
Rint | 0.031 | 0.085 | 0.064 | 0.055 |
(sin θ/λ)max (Å−1) | 0.665 | 0.617 | 0.639 | 0.628 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.079, 1.09 | 0.101, 0.181, 1.20 | 0.061, 0.148, 1.07 | 0.075, 0.156, 1.11 |
No. of reflections | 4762 | 5021 | 4782 | 8309 |
No. of parameters | 245 | 297 | 271 | 517 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
w = 1/[σ2(Fo2) + (0.025P)2 + 1.3P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.04P)2 + 12P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.067P)2] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.04P)2 + 1.2P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.47, −0.43 | 0.39, −0.27 | 0.37, −0.39 | 0.52, −0.40 |
Computer programs: SMART (Siemens, 1995), SAINT (Siemens, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···O1i | 0.81 (2) | 2.20 (2) | 2.981 (2) | 162 (2) |
C3—H3A···O1i | 0.95 | 2.59 | 3.481 (3) | 156.2 |
C15—H15A···O1i | 0.95 | 2.55 | 3.254 (2) | 130.7 |
C9—H9A···N1ii | 0.95 | 2.60 | 3.542 (3) | 172.3 |
C12—H12A···O3iii | 0.95 | 2.50 | 3.398 (2) | 156.6 |
C4—H4A···Br1iv | 0.95 | 3.25 | 3.968 (2) | 134.2 |
C18—H18B···Br1v | 0.99 | 3.19 | 3.920 (3) | 132.0 |
C17—H17A···C11vi | 0.98 | 2.84 | 3.786 (4) | 161.4 |
C17—H17A···C12vi | 0.98 | 2.74 | 3.646 (4) | 153.2 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x, y, z−1; (iii) −x+1, −y+1, −z+1; (iv) x+1/2, −y+1/2, z−1/2; (v) −x+3/2, y+1/2, −z+3/2; (vi) −x+3/2, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3A···O1i | 0.95 | 2.60 | 3.543 (5) | 175.1 |
C7—H7A···O2ii | 0.95 | 2.54 | 3.421 (5) | 154.5 |
C20—H20A···O1i | 0.98 | 2.49 | 3.392 (5) | 152.6 |
Symmetry codes: (i) −x+1/2, −y+3/2, −z+1/2; (ii) −x+1/2, y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···O1i | 0.88 (3) | 2.21 (3) | 3.066 (3) | 165 (3) |
C15—H15A···O1i | 0.95 | 2.44 | 3.225 (3) | 139.7 |
C3—H3A···O1i | 0.95 | 2.71 | 3.629 (3) | 161.8 |
C6—H6A···F1ii | 0.95 | 2.67 | 3.424 (3) | 136.4 |
C14—H14A···F1iii | 0.95 | 2.76 | 3.442 (3) | 129.3 |
C21—H21B···Cg(C10–C15)iv | 0.98 | 2.83 | 3.785 (3) | 166 |
C21—H21C···Cg(C2–C7)iv | 0.98 | 2.95 | 3.713 (4) | 135 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+1, −z+2; (iii) −x, −y+2, −z+2; (iv) −x+2, −y+1, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···O4i | 0.85 (3) | 2.08 (3) | 2.906 (3) | 166 (3) |
N2—H2A···O1i | 0.86 (3) | 2.19 (3) | 3.013 (3) | 162 (2) |
C15—H15A···O4i | 0.95 | 2.56 | 3.309 (3) | 136.3 |
C32—H32A···O1ii | 0.95 | 2.44 | 3.349 (4) | 160.7 |
C38—H38A···O1i | 0.95 | 2.48 | 3.283 (3) | 142.7 |
C7—H7A···O5iii | 0.95 | 2.63 | 3.457 (4) | 146.3 |
C18—H18B···Cg(C35/C36/C43–C46)iv | 0.99 | 2.48 | 3.439 (4) | 163 |
C19—H19A···Cg(C33–C38)iv | 0.98 | 2.92 | 3.591 (5) | 127 |
C23—H23A···Cg(C25–C30) | 0.95 | 2.86 | 3.735 (4) | 153 |
C41—H41B···Cg(C12/C13/C20–C23)v | 0.99 | 2.78 | 3.649 (3) | 147 |
C42—H42A···Cg(C10–C15)v | 0.98 | 2.88 | 3.609 (3) | 132 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) −x, −y+1, −z+1; (iv) x, y, z−1; (v) x, y+1, z. |
C1—N1—C10—C11 | C2—C1—N1—C10 | C3—C2—C1—N1 | O1—P1—C1—N1 | |
(I) | -26.6 (3) | -64.5 (2) | -50.0 (2) | 62.66 (15) |
(II) | -24.5 (6) | -61.1 (5) | -47.5 (5) | 50.6 (4) |
(III) | -29.9 (3) | -68.2 (3) | -44.1 (3) | 44.5 (2) |
(IV), molecule A | -13.9 (4) | -67.3 (3) | -39.3 (4) | 62.4 (2) |
(IV), molecule B | -23.5 (4) | -67.9 (3) | -59.7 (3) | 57.5 (2) |
(a) | -14.4 | -70.2 | -38.5 | 55.2 |
(b) | -12.6 | -64.3 | -41.0 | 56.7 |
(c) | -11.3 | -72.2 | -39.0 | 53.9 |
(d) | -12.0 | -75.0 | -52.4 | 51.8 |
(e) | -6.0 | -134.6 | -56.5 | 44.9 |
(f) | -0.9 | -68.9 | -37.9 | 51.6 |
(g), molecule A | 0.6 | -82.7 | -50.9 | 54.2 |
(g), molecule B | 4.2 | -135.4 | -69.8 | 58.3 |
(g), molecule C | -16.4 | -68.1 | -54.4 | 54.1 |
(h) | 11.6 | -146.8 | -66.2 | 56.7 |
(i), molecule A | -19.6 | -73.5 | -40.2 | 57.1 |
(i), molecule B | -19.1 | -66.2 | -41.8 | 47.7 |
(j), molecule A | -16.5 | -68.3 | -34.2 | 47.2 |
(j), molecule B | -21.9 | -73.5 | -36.8 | 57.5 |
(k) | -14.0 | -68.8 | -48.7 | 46.9 |
(l) | 8.6 | -113.9 | -32.8 | 58.0 |
Notes: (a) diethyl anilinobenzylphosphonate (Rużić-Toroš et al., 1978); (b) N,N'-bis[(dimethoxyphosphinoyl)phenylmethyl]-1,4-diaminobenzene (Nastopoulos et al., 1987); (c) N,N'-bis[(diethoxyphosphinoyl)phenylmethyl]-1,4-diaminobenzene (Nastopoulos et al., 1987); (d) diethyl [anilino(1,3-benzodioxol-5-yl)methyl]phosphonate (Kidwai et al., 2011); (e) O,O'-di-n-propyl-α-(4-bromophenylamino)-3,4,5- trimethoxybenzylphosphonate (Li et al., 2007); (f) 1-(4-{[(1,3-benzodioxol-5-yl)(diethoxyphosphoroyl)methyl]amino}phenyl)ferrocene (Lu et al., 2008); (g) diisopropyl(anilino(phenyl)methyl)phosphonate (Fang et al., 2011); (h) diethyl{(4-fluorophenyl)[4-(trifluoromethyl)phenylamino]methyl}phosphonate (Song et al., 2003); (i) diisopropyl{(4-bromophenyl)[(4-bromophenyl)amino]methyl}phosphonate (Babashkina et al., 2009); (j) diisopropyl{(4-bromophenyl)[(4-methoxyphenyl)amino]methyl}phosphonate (Babashkina et al., 2009); (k) diisopropyl[anilino(4-bromophenyl)methyl]phosphonate (Babashkina et al., 2009); (l) {3-[(1,3-benzodioxol-5-yl)(diethyl phosphonato)methylamino]phenyl}ferrocene (Feng et al., 2010). |