Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616001595/fp3025sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229616001595/fp3025Isup2.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616001595/fp3025Isup6.cml | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229616001595/fp3025IIsup3.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616001595/fp3025IIsup7.cml | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229616001595/fp3025IIIsup4.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616001595/fp3025IIIsup8.cml | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229616001595/fp3025IVsup5.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616001595/fp3025IVsup9.cml | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229616001595/fp3025sup10.pdf |
CCDC references: 1449952; 1449951; 1449950; 1449949
Phosphoric triamides are attractive to study owing to their extensive applications in biochemistry (Domínguez et al., 2008) and using as O-donor ligands (Gholivand et al., 2010).
Recently, we have investigated the syntheses and crystal structures of racemic mixed-amide phosphinates with an (N1)P(═O)(OC6H5)(N2) segment, where N1 and N2 belong to two different –NRxRy groups (Rx ≠ H; Ry = H or ≠ H) (Pourayoubi et al., 2011, 2013).
Racemic Cl(R1R2N)P(O)(OC6H5) phosphorus–chlorine reagents (NR1R2 = NH-cyclo-C6H11 and NH—C6H4-4-CH3) were used in reactions with different amines (Pourayoubi et al., 2011, 2013). In these reactions, the most challenging tasks are related to the synthesis of racemic Cl(R1R2N)P(O)(OC6H5) phosphorus–chlorine compounds [from the commercial (C6H5O)P(O)Cl2 reagent and two molar equivalents of the amine NHR1R2] and then separation of the racemic reagent from the [R1R2NH2]Cl alkyl/aryl ammonium chloride by-product.
It is necessary to select a suitable solvent with considerable differences of solubility for the phosphorus–chlorine reagent and the amine hydrochloride salt in order to obtain a pure product. Acetonitrile appears to be a good choice, with a high solubility for ClP(O)(OR)[NH(cyclo-C6H11)] or ClP(O)(OR)(NH—C6H4-4-CH3) and a low solubility for the related amine hydrochloride salt.
Controlling the amount of precipitate formed is also necessary, which was achieved by a careful selection of the volume of solvent. A high volume of solvent leads to greater dissolution of the [R1R2NH2]Cl salt, which should be avoided as it leads to salt impurities in the acetonitrile solution of the phosphorus–chlorine reagent. On the other hand, a low volume of solvent reduces the amount of phosphorus–chlorine compound in solution, causing precipitation of a portion of the reagent, and this may also lead to the formation of the fully amide-substituted dechlorinated compound. So, in order to successfully prepare a pure phosphorus–chlorine reagent, one needs to control the mass of precipitate formed to achieve a mass near to what is calculated for the salt from the stoichiometry of reaction.
After completion of the reaction, the [R1R2NH2]Cl by-product was removed by filtration (Pourayoubi et al., 2013; Sabbaghi et al., 2011; Ghadimi et al., 2009). It should be mentioned that, although H2O is usually used for removing the [R1R2NH2]Cl salts in the preparation of compounds such as phosphoric triamide (which does not include phosphorus–halogen bonds), it could not be used for removing the [R1R2NH2]Cl by-product in the purification of the phosphorus–chlorine reagent.
With these elements in mind concerning the synthesis of racemic mixed-amide phosphinates, we decided to design experiments for the preparation of mixed-amide phosphoric triamides, especially phosphoric triamides having three differently substituted amide groups, with the P atom in a chiral environment. A search in the Cambridge Structural Database (CSD, Version 5.35, February 2014 update; Groom & Allen, 2014) for the P(O)[N]3 motif in phosphoric triamides gives possible structures with the formulae P(O)[NHR1]3, P(O)[NR1R2]3, P(O)[NHR1][NR2R3]2 and P(O)[NHR1]2[NR2R3] (R1–3 = H or a hydrocarbon segment and NHR1, NR1R2 and NR2R3 ≠ NH2). For the case of P(O)[NR1R2][NR3R4][NR5R6] (NR1R2 ≠ NR3R4 ≠ NR5R6), however, no structure was found in the CSD. In other words, no structure could be found for acyclic compounds including a chiral P atom in a P(═O)(N1)(N2)(N3) environment (N1, N2 and N3 indicate the N atoms of three different NRxRy groups). Some cyclic compounds have been reported; see (A) in Scheme 1 for a typical example (Denmark et al., 2006).
In the present study, we present the first structures of examples of acyclic racemic phosphoric triamides having three differently substituted amide groups, with a P(═O)(N1)(N2)(N3) skeleton, i.e. rac-LP(O)[N(CH3)(C6H11](NHC6H11) [L = NHC(CH3)3 in (I) and NHC6H4-p-CH3 in (II)]. Moreover, the crystal structures of the mixed-amide phosphoric triamides (C6H11NH)2P(O)[N(CH3)(C6H11)], (III), and (C5H10)(NH)2P(O)[N(CH3)(C6H11)], (IV), having the same P(O)[N(CH3)(C6H11)] part as (I) and (II), were also studied.
It should be noted that the description mixed-amide phosphoric triamides refers to compounds with the general formula P(O)(NR1R2)(NR3R4)(NR5R6) [R1–6 = H or a hydrocarbon segment, and NR1R2 ≠ NR3R4 ≠ NR5R6], which are also referred to as mixed triamide phosphine oxides.
The starting phosphorus–chlorine compound Cl2P(O)[N(CH3)(C6H11)] was synthesized at 273 K by the reaction of NH(CH3)(C6H11) (20 mmol) dissolved in dry acetonitrile (10 ml) with a solution of P(O)Cl3 (10 mmol) in the same solvent (20 ml). After stirring for 5 h, the solid which formed, i.e. (C6H11)(CH3)NH·HCl, was filtered off. The acetonitrile solution of Cl2P(O)[N(CH3)(C6H11)] was used for the next step. The other starting compound, i.e. rac-ClP(O)[N(CH3)(C6H11)](NHC6H11) was synthesized from Cl2P(O)[N(CH3)(C6H11)] using the same procedure, but using Cl2P(O)[N(CH3)(C6H11)] as the starting phosphorus–chlorine compound in the reaction with NH2(C6H11).
For the synthesis of (I), a solution of tert-butylamine (4 mmol) in dry acetonitrile (10 ml) was added to a solution of ClP(O)[N(CH3)(C6H11)](NHC6H11) (2 mmol) in the same solvent (20 ml) at 273 K. After stirring for 7 h, the solvent was removed in vacuo and the solid obtained was washed with distilled water.
Compound (II) was synthesized following the same procedure but by using a mixture of p-toluidine and triethylamine (2 mmol of each) instead of tert-butylamine. Colourless single crystals suitable for X-ray diffraction experiments were obtained at room temperature from CH3OH/CHCl3/DMF (4:4:1 v/v/v) for (I) and from CHCl3/C2H5OH (4:1 v/v) for (II).
For the synthesis of (III), a solution of cyclohexylamine (8 mmol) in dry acetonitrile (10 ml) was added to a solution of Cl2P(O)[N(CH3)(C6H11)] (2 mmol) in the same solvent (20 ml) at 273 K. After stirring for 4 h, the solvent was removed in vacuo and the solid obtained was washed with distilled water.
Compound (IV) was obtained using a similar procedure as for (III), but using 2,2-dimethylpropane-1,3-diamine (4 mmol) instead of cyclohexylamine. Colourless single crystals suitable for X-ray diffraction experiments were obtained at room temperature from CHCl3/C2H5OH (2:2 v/v) for (III) and from CH3OH/DMF (4:1 v/v) for (IV). The 1H NMR, 13C NMR and MS spectra of compounds (I)–(IV) are given in Figs. S1–S15 in the Supporting information.
IR (KBr disc, ν, cm−1): 3251, 2931, 2853, 1451, 1369, 1230, 1195, 1121, 1014, 972, 889, 765.MS (70 ev, EI): m/z (%) = 330 (12) [M + 1]+, 329 (73) [M]+, 327 (92) [M − 2]+, 256 (57) [M - tBuNH2]+, 231 (45) [M - C6H11NH]+, 216 (56) [M - (C6H11)NH(CH3)]+, 174 (41) [(C6H11N(CH3))P(O)NH]+, 112 (100) [C7H14N]+, 98 (82) [C6H10NH2]+, 71 (9) [C4H9N]+ [for reporting of relative intensities, the intensity of base peak in Fig. S9 (93%) (see Supporting information was changed to 100% and the intensities of the other peaks were corrected by a factor of 100/93]. 31P{1H} NMR (121.78 MHz, CDCl3, 303.2 K, 85% H3PO4): δ 15.58 (s). 1H NMR (300.85 MHz, CDCl3, 294.9 K, TMS): δ 0.836–2.16 (m, 20H, CH2), 1.29 (s, 9H, 3CH3), 2.50 (m, 3H, CH3—N), 2.60 (s, 1H, NH), 2.86 (m, 1H, NH), 2.77–2.93 (m, 2H, 1CH and 1NH of C6H11NH), 3.37–3.53 (m, 1H, CH). 13C NMR (75.65 MHz, CDCl3, 295.7 K, TMS): δ 25.24 (d, JC–P = 5.3 Hz), 25.56 (s), 25.69 (s), 26.05 (s), 27.86 (d, JC–P = 5.3 Hz), 28.91 (s), 29.75 (s) 31.75 (d, JC–P = 4.5 Hz), 36.17 (d, JC–P = 4.5 Hz), 36.32 (d, JC–P = 5.3 Hz), 50.02 (s), 54.45 (d, JC–P = 4.5 Hz).
IR (KBr disc, ν, cm−1): 3275, 2925, 2851, 1617, 1517, 1446, 1395, 1297, 1169, 1113, 1009, 976, 933, 816. MS (70 ev, EI): m/z (%) = 363 (5) [M]+, 362 (48) [M − 1]+, 361 (92) [M − 2]+, 197 (20) [{(4-CH3)C6H4NH}P(O)(NCH3)(NH)]+, 182 (17) [{(4-CH3)C6H4NH}P(O)(NCH3)]+, 168 (24) [{(4-CH3)C6H4NH}P(O)(NH)]+, 153 (10) [{(4-CH3)C6H4NH}P(O)]+, 112 (100) [C6H11N(CH3)]+, 106 (90) [(4-CH3)C6H4NH]+, 98 (70) [C6H11NH]+, 83 (89) [C6H11]+. 31P{1H} NMR (121.78 MHz, CDCl3, 303.2 K, 85% H3PO4): δ 11.00 (s). 1H NMR (300.85 MHz, CDCl3, 295.7 K, TMS): δ 0.99–2.09 (m, 20H, CH2), 2.25 (s, 3H, CH3), 2.56 (m, 3H, CH3—N), 3.04–3.09 (m, 2H, 1CH and 1NH of C6H11NH), 3.46–3.60 (m, 1H, CH), 5.05 (d, 2JH–P = 7.8 Hz, 1H, NH), 6.91 (d, 3JH–H = 8.4 Hz, 2H, Ar—H), 7.00 (d, 3JH–H = 8.1 Hz, 2H, Ar—H). 13C NMR (75.65 MHz, CDCl3, 295.7 K, TMS): δ 20.55 (s, 1 C, CH3), 25.24 (d, JC–P = 7.6 Hz), 25.46 (s), 25.61 (s), 26.00 (s), 27.72 (d, JC–P = 5.3 Hz), 31.10 (d, JC–P = 2.3 Hz), 36.12 (d, JC–P = 6.1 Hz), 36.23 (d, JC–P = 4.5 Hz), 50.01 (s), 54.72 (d, JC–P = 3.8 Hz), 117.74 (d, JC–P) = 6.8 Hz), 129.50 (s), 129.92 (s), 138.74 (s).
IR (KBr disc, ν, cm−1): 3268, 2930, 2853, 1450, 1430, 1270, 1226, 1183, 1160, 1103, 1013, 977, 898. MS (70 ev, EI): m/z (%) = 356 (20) [M + 1]+, 355 (82) [M]+, 354 (86) [M − 1]+, 256 (65) [M - C6H11NH2]+, 174 (58) [(C6H11N(CH3))P(O)NH]+, 159 (25) [(C6H11N(CH3))P(O)]+, 112 (100) [C6H11N(CH3)]+, 98 (83) [C6H11NH]+, 83 (63) [C6H11]+. 31P{1H} NMR (121.78 MHz, CDCl3, 303.2 K, 85% H3PO4): δ 15.25 (s). 1H NMR (300.85 MHz, CDCl3, 294.5 K, TMS): δ 0.94–2.02 (m, 30H, CH2), 2.51 (d, 3JH–P = 9.9 Hz, 3H, CH3), 2.95 (m, 2H, NH), 3.44–3.54 (m, 2H and 1H, CH of C6H11 groups). 13C NMR (75.65 MHz, CDCl3, 295.8 K, TMS): δ 25.21 (d, JC–P = 3.0 Hz), 25.49 (s), 25.63 (s), 25.97 (s), 27.72 (d, JC–P = 4.5 Hz), 31.18 (d, JC–P = 2.3 Hz), 36.27 (d, JC–P = 4.5 Hz), 36.50 (d, JC–P = 4.5 Hz), 49.86 (s), 54.30 (d, JC–P = 3.8 Hz).
IR (KBr disc, ν, cm−1): 3224, 3182, 2937, 2852, 1438, 1200, 1111, 1005, 962, 856, 701. MS (70 ev, EI): m/z (%) = 260 (4) [M + 1]+, 259 (40) [M]+, 258 (81) [M − 1]+, 243 (21) [M - CH4]+, 147 (81) [M - N(CH3)(C6H11)]+, 112 (100) [C6H11N(CH3)]+, 98 (29) [C6H11NH]+, 84 (27) [C6H12]+. 31P{1H} NMR (162.01 MHz, DMSO-d6, 294.9 K, 85% H3PO4): δ 14.78 (s). 1H NMR (400.22 MHz, DMSO-d6, 294.7 K, TMS): δ 0.75 (s, 3H, CH3), 0.98 (s, 3H, CH3), 1.00–1.76 (m, 10H, CH2 of cyclohexyl), 2.46 (d, 3JH–P = 10.7 Hz, 3H, CH3—N), 2.59 (m, 4H, CH2), 3.29 (m, 1H, CH of cyclohexyl), 3.99 (m, 2H, NH). 13C NMR (100.63 MHz, DMSO-d6, 295.0 K, TMS): δ 23.66 (s), 25.18 (s), 25.78 (s), 26.27 (s), 26.89 (s), 26.93 (s), 30.33 (d, JC–P = 5.6 Hz), 31.19 (d, JC–P = 3.6 Hz), 53.71 (d, JC–P = 2.9 Hz), 53.82 (d, JC–P = 3.5 Hz), 53.87 (s).
Crystal data, data collection and structure refinement details are summarized in Table 1. Non-H atoms were refined anisotropically. H atoms were all located in the difference Fourier maps for each of the title structures, but those attached to C atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularize their geometry (C—H in the range 0.92 – 1.00 Å de pending on hybridization state), after which the positions of H-atoms not involved in hydrogen bonding interactions were refined with riding constraints (Cooper et al., 2010) and fixed isotropic displacement parameters Uiso(H) = 1.5Ueq(Ci) for CH3 groups or 1.2Ueq(Cii) for CH2 and CH groups, where Ueq(Ci) and Ueq(Cii) are the equivalent displacement parameters of the C atoms to which corresponding H atoms are bonded. The H atoms of the NH groups were allowed to refine with a restrained N—H bond distance of 0.86 (2) Å and Uiso(H) = 1.2Ueq(N). The H atoms of the NH groups were refined using soft distance and angle restraints.
In (I), the absolute configuration was arbitrarily assigned. One independent molecule of (I) appeared to be heavily disordered. This disorder was modelled with split positions. Two orientations of tert-butyl were found, and they were restrained to have a similar geometry. In addition restraints were used in order to keep reasonable C—C sp3-sp3 bond distances. The anisotropic atomic displacement parameters of adjacent atoms in the disordered fragment were restrained to be the same (Betteridge et al., 2003). The similarity restraint was not used for the two disordered parts of the cyclohexane group of the same molecule. Instead, only the anisotropic atomic displacement parameters of adjacent atoms were restrained to be the same, and restraints were used in order to keep reasonable C—C sp3-sp3 bond distances within the rings. The occupancies of the two parts for tert-butyl and cyclohexane were refined to 0.233 (9)/0.767 (9) and 0.443 (11)/0.557 (9), respectively.
In (III), disorder on all six-membered rings appeared to be impossible to model satisfactorily using split positions. For this reason restraints on angles and distances were used in order to get an acceptable geometry. It was in addition necessary to use thermal similarity restraints on all atoms within the rings.
Although the general structural features are certainly correct in (I) and (III), some caution is necessary when interpreting the fine structural details in especially the disordered parts.
Cl2P(O)[N(CH3)(cyclo-C6H11)] was synthesized from the reaction between Cl3P(O) and N-methylcyclohexylamine (1:2 molar ratio). Racemic ClP(O)[N(CH3)(cyclo-C6H11)][NH(cyclo-C6H11)] was then prepared from Cl2P(O)[N(CH3)(cyclo-C6H11)]and cyclohexylamine (1:2 molar ratio), for the first time. In each reaction, the corresponding amine acts as both a nucleophile and an HCl scavenger.
Acetonitrile was found to be a suitable solvent in these reactions, due to the low solubility of the [(cyclo-C6H11)NH2(CH3)]Cl (first reaction) and [(cyclo-C6H11)NH3]Cl (second reaction) salts and the good solubility of Cl2P(O)[N(CH3)(cyclo-C6H11)] and ClP(O)[N(CH3)(cyclo-C6H11)][NH(cyclo-C6H11)]. Thus, the salts formed in each reaction were simply filtered off and the pure products Cl2P(O)[N(CH3)(cyclo-C6H11)] and ClP(O)[N(CH3)(cyclo-C6H11)][NH(cyclo-C6H11)] remained in the acetonitrile solution.
In the final step, for the preparation of (I) and (II) (see Scheme 2), rac-ClP(O)[N(CH3)(cyclo-C6H11)][NH(cyclo-C6H11)] reacts with the corresponding amine [2 eqivalents of tert-butylamine for (I) and an equimolar mixture of p-toluidine and triethylamine for (II)] to yield the racemic (RNH)P(O)[N(CH3)(cyclo-C6H11)][NH(cyclo-C6H11)] mixed phosphoric triamides [R = t-Bu in (I) and 4-CH3—C6H4 in (II)], and the [tBuNH3]Cl salt for (I) and 4-CH3—C6H4NH3Cl for (II)) were removed by dissolving in H2O.
The phosphoric triamides (III) and (IV) were prepared from the reaction between an acetonitrile solution of Cl2P(O)[N(CH3)(cyclo-C6H11)] and the corresponding amine. The salts which formed were removed with H2O (see Scheme 2).
The molecular structures of triamides (I)–(IV) are shown in Figs. 1–4, respectively, indicating four, three, two and one molecule in the asymmetric units. In all four compounds, the P atoms display a distorted tetrahedral environment, as (N1)P(═O)(N2)(N3) for (I) and (II), and as (N1)P(═O)(N2)2 for (III) and (IV), where N1, N2 and N3 in (I) and (II) denote the N atoms of three different groups. On the other hand, the two N2 atoms in (III) belong to two chemically (and not crystallographically) equivalent groups containing N atoms, and in (IV), N2 is related to a bifunctional group containing two chemically equivalent N atoms.
Selected bond lengths and angles of (I)–(IV) are given in Tables 2–5, respectively. The P═O bond lengths and O═P—N and P—N—C bond angles are comparable with those in similar compounds (Pourayoubi et al., 2012, 2014).
The bond-angle sums at the tertiary N atoms of the P—N(CH3)(C6H11) segment in (I)–(IV), i.e. P—N—C + C—N—C + C—N—P, confirm the sp2 character of such N atoms, for example, bond-angle sums of 358.31 (2), 359.03 (1) and 357.33 (2)° in the three independent molecules of (II).
In compound (IV), the P═O bond is located in the equatorial 2-position of the 1,3,2-diazaphosphorinane ring, and the P—N bond made by the –N(CH3)(C6H11) segment is in the axial position.
The P—N bonds formed by the relatively bulky –N(CH3)(C6H11) segment are longer than those formed by the tert-C4H9NH– and –NHCH2C(CH3)2CH2NH– segments. For example, we note the P—N bond in structure (IV), made by the –N(CH3)(C6H11) and –NHCH2C(CH3)2CH2NH— segments is 1.6672 (18) Å for the former and 1.6440 (18) and 1.628 (2) Å for the latter.
Moreover, among the nine molecules in the three structures including both –N(CH3)(C6H11) and –NHC6H11 segments, for eight of the molecules, longer P—N bonds were found involving –N(CH3)(C6H11). For example, note P1—N3 = 1.6405 (16) Å and P1—N11 1.6300 (16) Å involving the –N(CH3)(C6H11) and C6H11NH– segments, respectively in (II). On the other hand, in one of the independent molecules of (III), a shorter P—N bond [1.650 (4) Å] was found made by –N(CH3)(C6H11) in comparison with the two C6H11NH– segments [1.680 (6) and 1.655 (7) Å]. [bond lengths don't match Table 4]
Surprisingly, in (II), the 4-CH3—C6H4NH– segment makes a longer P—N bond with respect to the –N(CH3)(C6H11) segment, which is attributed to the different hybridization states of the C atoms attached to the N atoms in these groups (sp2 and sp3, respectively), resulting in an electron-withdrawing effect of the aromatic ring. This is similar to what was reported previously for the P—N bonds made by the same groups in rac-(C6H5O)P(O)[N(CH3)(cyclo-C6H11)][NH(C6H4-p-CH3)] (Pourayoubi et al., 2013).
In some molecules of structures (I)–(IV), the C—N—C angles of the –N(CH3)(C6H11) segments are smaller than the two related P—N—C angles; however, there are also the cases where the C—N—C angle is larger than one of the P—N—C angles at the same N atom. For example, in one of the molecules in structure (II), the C—N—C and two P—N—C angles are 118.96 (16), 121.69 (13) and 118.38 (14)°, respectively.
The extended structure of (I) includes four independent molecules in a one-dimensional chain aggregation (Fig. 5). In this chain, adjacent molecules are linked via (N—H···)2O═P and (N—H···)O═P hydrogen bonds along [001], building two different and two different C(4) motifs with an C(4)C(4) arrangement (Table 6).
In the crystal packing of (II), each P═O group takes part with two N—H units in intermolecular (N—H···)2O═P hydrogen bonds, forming three different rings in a one-dimensional chain containing three independent molecules, running along [100] (Fig. 6 and Table 7).
The hydrogen-bond pattern of (III) is similar to that of (II), with adjacent molecules linked through (N—H···)2O═P hydrogen bonds in a one-dimensional chain along [010], with building motifs (Fig. 7 and Table 8).
The crystal packing of (IV) is slightly different, with molecules connected through (N—H···)(N—H···)O═P hydrogen bonds, forming ring motifs, into extended chains parallel to [100] (Fig. 8 and Table 9).
According to the hydrogen-bond patterns discussed, (N—H···)2O═P and (N—H···)(N—H···)O═P refer to the double-acceptor action of O atoms. The former notation was used when two N—H groups belong to one molecule (in a ring motif) and the latter is used for the case with two N—H groups belonging to individual molecules (forming a ring motif). On the other hand, the structure of (I) also includes a two-centred hydrogen bond, forming a C(4) motif, and there are some N—H groups which are not involved in hydrogen-bond interactions.
Phosphoric triamides are attractive to study owing to their extensive applications in biochemistry (Domínguez et al., 2008) and using as O-donor ligands (Gholivand et al., 2010).
Recently, we have investigated the syntheses and crystal structures of racemic mixed-amide phosphinates with an (N1)P(═O)(OC6H5)(N2) segment, where N1 and N2 belong to two different –NRxRy groups (Rx ≠ H; Ry = H or ≠ H) (Pourayoubi et al., 2011, 2013).
Racemic Cl(R1R2N)P(O)(OC6H5) phosphorus–chlorine reagents (NR1R2 = NH-cyclo-C6H11 and NH—C6H4-4-CH3) were used in reactions with different amines (Pourayoubi et al., 2011, 2013). In these reactions, the most challenging tasks are related to the synthesis of racemic Cl(R1R2N)P(O)(OC6H5) phosphorus–chlorine compounds [from the commercial (C6H5O)P(O)Cl2 reagent and two molar equivalents of the amine NHR1R2] and then separation of the racemic reagent from the [R1R2NH2]Cl alkyl/aryl ammonium chloride by-product.
It is necessary to select a suitable solvent with considerable differences of solubility for the phosphorus–chlorine reagent and the amine hydrochloride salt in order to obtain a pure product. Acetonitrile appears to be a good choice, with a high solubility for ClP(O)(OR)[NH(cyclo-C6H11)] or ClP(O)(OR)(NH—C6H4-4-CH3) and a low solubility for the related amine hydrochloride salt.
Controlling the amount of precipitate formed is also necessary, which was achieved by a careful selection of the volume of solvent. A high volume of solvent leads to greater dissolution of the [R1R2NH2]Cl salt, which should be avoided as it leads to salt impurities in the acetonitrile solution of the phosphorus–chlorine reagent. On the other hand, a low volume of solvent reduces the amount of phosphorus–chlorine compound in solution, causing precipitation of a portion of the reagent, and this may also lead to the formation of the fully amide-substituted dechlorinated compound. So, in order to successfully prepare a pure phosphorus–chlorine reagent, one needs to control the mass of precipitate formed to achieve a mass near to what is calculated for the salt from the stoichiometry of reaction.
After completion of the reaction, the [R1R2NH2]Cl by-product was removed by filtration (Pourayoubi et al., 2013; Sabbaghi et al., 2011; Ghadimi et al., 2009). It should be mentioned that, although H2O is usually used for removing the [R1R2NH2]Cl salts in the preparation of compounds such as phosphoric triamide (which does not include phosphorus–halogen bonds), it could not be used for removing the [R1R2NH2]Cl by-product in the purification of the phosphorus–chlorine reagent.
With these elements in mind concerning the synthesis of racemic mixed-amide phosphinates, we decided to design experiments for the preparation of mixed-amide phosphoric triamides, especially phosphoric triamides having three differently substituted amide groups, with the P atom in a chiral environment. A search in the Cambridge Structural Database (CSD, Version 5.35, February 2014 update; Groom & Allen, 2014) for the P(O)[N]3 motif in phosphoric triamides gives possible structures with the formulae P(O)[NHR1]3, P(O)[NR1R2]3, P(O)[NHR1][NR2R3]2 and P(O)[NHR1]2[NR2R3] (R1–3 = H or a hydrocarbon segment and NHR1, NR1R2 and NR2R3 ≠ NH2). For the case of P(O)[NR1R2][NR3R4][NR5R6] (NR1R2 ≠ NR3R4 ≠ NR5R6), however, no structure was found in the CSD. In other words, no structure could be found for acyclic compounds including a chiral P atom in a P(═O)(N1)(N2)(N3) environment (N1, N2 and N3 indicate the N atoms of three different NRxRy groups). Some cyclic compounds have been reported; see (A) in Scheme 1 for a typical example (Denmark et al., 2006).
In the present study, we present the first structures of examples of acyclic racemic phosphoric triamides having three differently substituted amide groups, with a P(═O)(N1)(N2)(N3) skeleton, i.e. rac-LP(O)[N(CH3)(C6H11](NHC6H11) [L = NHC(CH3)3 in (I) and NHC6H4-p-CH3 in (II)]. Moreover, the crystal structures of the mixed-amide phosphoric triamides (C6H11NH)2P(O)[N(CH3)(C6H11)], (III), and (C5H10)(NH)2P(O)[N(CH3)(C6H11)], (IV), having the same P(O)[N(CH3)(C6H11)] part as (I) and (II), were also studied.
It should be noted that the description mixed-amide phosphoric triamides refers to compounds with the general formula P(O)(NR1R2)(NR3R4)(NR5R6) [R1–6 = H or a hydrocarbon segment, and NR1R2 ≠ NR3R4 ≠ NR5R6], which are also referred to as mixed triamide phosphine oxides.
IR (KBr disc, ν, cm−1): 3251, 2931, 2853, 1451, 1369, 1230, 1195, 1121, 1014, 972, 889, 765.MS (70 ev, EI): m/z (%) = 330 (12) [M + 1]+, 329 (73) [M]+, 327 (92) [M − 2]+, 256 (57) [M - tBuNH2]+, 231 (45) [M - C6H11NH]+, 216 (56) [M - (C6H11)NH(CH3)]+, 174 (41) [(C6H11N(CH3))P(O)NH]+, 112 (100) [C7H14N]+, 98 (82) [C6H10NH2]+, 71 (9) [C4H9N]+ [for reporting of relative intensities, the intensity of base peak in Fig. S9 (93%) (see Supporting information was changed to 100% and the intensities of the other peaks were corrected by a factor of 100/93]. 31P{1H} NMR (121.78 MHz, CDCl3, 303.2 K, 85% H3PO4): δ 15.58 (s). 1H NMR (300.85 MHz, CDCl3, 294.9 K, TMS): δ 0.836–2.16 (m, 20H, CH2), 1.29 (s, 9H, 3CH3), 2.50 (m, 3H, CH3—N), 2.60 (s, 1H, NH), 2.86 (m, 1H, NH), 2.77–2.93 (m, 2H, 1CH and 1NH of C6H11NH), 3.37–3.53 (m, 1H, CH). 13C NMR (75.65 MHz, CDCl3, 295.7 K, TMS): δ 25.24 (d, JC–P = 5.3 Hz), 25.56 (s), 25.69 (s), 26.05 (s), 27.86 (d, JC–P = 5.3 Hz), 28.91 (s), 29.75 (s) 31.75 (d, JC–P = 4.5 Hz), 36.17 (d, JC–P = 4.5 Hz), 36.32 (d, JC–P = 5.3 Hz), 50.02 (s), 54.45 (d, JC–P = 4.5 Hz).
IR (KBr disc, ν, cm−1): 3275, 2925, 2851, 1617, 1517, 1446, 1395, 1297, 1169, 1113, 1009, 976, 933, 816. MS (70 ev, EI): m/z (%) = 363 (5) [M]+, 362 (48) [M − 1]+, 361 (92) [M − 2]+, 197 (20) [{(4-CH3)C6H4NH}P(O)(NCH3)(NH)]+, 182 (17) [{(4-CH3)C6H4NH}P(O)(NCH3)]+, 168 (24) [{(4-CH3)C6H4NH}P(O)(NH)]+, 153 (10) [{(4-CH3)C6H4NH}P(O)]+, 112 (100) [C6H11N(CH3)]+, 106 (90) [(4-CH3)C6H4NH]+, 98 (70) [C6H11NH]+, 83 (89) [C6H11]+. 31P{1H} NMR (121.78 MHz, CDCl3, 303.2 K, 85% H3PO4): δ 11.00 (s). 1H NMR (300.85 MHz, CDCl3, 295.7 K, TMS): δ 0.99–2.09 (m, 20H, CH2), 2.25 (s, 3H, CH3), 2.56 (m, 3H, CH3—N), 3.04–3.09 (m, 2H, 1CH and 1NH of C6H11NH), 3.46–3.60 (m, 1H, CH), 5.05 (d, 2JH–P = 7.8 Hz, 1H, NH), 6.91 (d, 3JH–H = 8.4 Hz, 2H, Ar—H), 7.00 (d, 3JH–H = 8.1 Hz, 2H, Ar—H). 13C NMR (75.65 MHz, CDCl3, 295.7 K, TMS): δ 20.55 (s, 1 C, CH3), 25.24 (d, JC–P = 7.6 Hz), 25.46 (s), 25.61 (s), 26.00 (s), 27.72 (d, JC–P = 5.3 Hz), 31.10 (d, JC–P = 2.3 Hz), 36.12 (d, JC–P = 6.1 Hz), 36.23 (d, JC–P = 4.5 Hz), 50.01 (s), 54.72 (d, JC–P = 3.8 Hz), 117.74 (d, JC–P) = 6.8 Hz), 129.50 (s), 129.92 (s), 138.74 (s).
IR (KBr disc, ν, cm−1): 3268, 2930, 2853, 1450, 1430, 1270, 1226, 1183, 1160, 1103, 1013, 977, 898. MS (70 ev, EI): m/z (%) = 356 (20) [M + 1]+, 355 (82) [M]+, 354 (86) [M − 1]+, 256 (65) [M - C6H11NH2]+, 174 (58) [(C6H11N(CH3))P(O)NH]+, 159 (25) [(C6H11N(CH3))P(O)]+, 112 (100) [C6H11N(CH3)]+, 98 (83) [C6H11NH]+, 83 (63) [C6H11]+. 31P{1H} NMR (121.78 MHz, CDCl3, 303.2 K, 85% H3PO4): δ 15.25 (s). 1H NMR (300.85 MHz, CDCl3, 294.5 K, TMS): δ 0.94–2.02 (m, 30H, CH2), 2.51 (d, 3JH–P = 9.9 Hz, 3H, CH3), 2.95 (m, 2H, NH), 3.44–3.54 (m, 2H and 1H, CH of C6H11 groups). 13C NMR (75.65 MHz, CDCl3, 295.8 K, TMS): δ 25.21 (d, JC–P = 3.0 Hz), 25.49 (s), 25.63 (s), 25.97 (s), 27.72 (d, JC–P = 4.5 Hz), 31.18 (d, JC–P = 2.3 Hz), 36.27 (d, JC–P = 4.5 Hz), 36.50 (d, JC–P = 4.5 Hz), 49.86 (s), 54.30 (d, JC–P = 3.8 Hz).
IR (KBr disc, ν, cm−1): 3224, 3182, 2937, 2852, 1438, 1200, 1111, 1005, 962, 856, 701. MS (70 ev, EI): m/z (%) = 260 (4) [M + 1]+, 259 (40) [M]+, 258 (81) [M − 1]+, 243 (21) [M - CH4]+, 147 (81) [M - N(CH3)(C6H11)]+, 112 (100) [C6H11N(CH3)]+, 98 (29) [C6H11NH]+, 84 (27) [C6H12]+. 31P{1H} NMR (162.01 MHz, DMSO-d6, 294.9 K, 85% H3PO4): δ 14.78 (s). 1H NMR (400.22 MHz, DMSO-d6, 294.7 K, TMS): δ 0.75 (s, 3H, CH3), 0.98 (s, 3H, CH3), 1.00–1.76 (m, 10H, CH2 of cyclohexyl), 2.46 (d, 3JH–P = 10.7 Hz, 3H, CH3—N), 2.59 (m, 4H, CH2), 3.29 (m, 1H, CH of cyclohexyl), 3.99 (m, 2H, NH). 13C NMR (100.63 MHz, DMSO-d6, 295.0 K, TMS): δ 23.66 (s), 25.18 (s), 25.78 (s), 26.27 (s), 26.89 (s), 26.93 (s), 30.33 (d, JC–P = 5.6 Hz), 31.19 (d, JC–P = 3.6 Hz), 53.71 (d, JC–P = 2.9 Hz), 53.82 (d, JC–P = 3.5 Hz), 53.87 (s).
The molecular structures of triamides (I)–(IV) are shown in Figs. 1–4, respectively, indicating four, three, two and one molecule in the asymmetric units. In all four compounds, the P atoms display a distorted tetrahedral environment, as (N1)P(═O)(N2)(N3) for (I) and (II), and as (N1)P(═O)(N2)2 for (III) and (IV), where N1, N2 and N3 in (I) and (II) denote the N atoms of three different groups. On the other hand, the two N2 atoms in (III) belong to two chemically (and not crystallographically) equivalent groups containing N atoms, and in (IV), N2 is related to a bifunctional group containing two chemically equivalent N atoms.
Selected bond lengths and angles of (I)–(IV) are given in Tables 2–5, respectively. The P═O bond lengths and O═P—N and P—N—C bond angles are comparable with those in similar compounds (Pourayoubi et al., 2012, 2014).
The bond-angle sums at the tertiary N atoms of the P—N(CH3)(C6H11) segment in (I)–(IV), i.e. P—N—C + C—N—C + C—N—P, confirm the sp2 character of such N atoms, for example, bond-angle sums of 358.31 (2), 359.03 (1) and 357.33 (2)° in the three independent molecules of (II).
In compound (IV), the P═O bond is located in the equatorial 2-position of the 1,3,2-diazaphosphorinane ring, and the P—N bond made by the –N(CH3)(C6H11) segment is in the axial position.
The P—N bonds formed by the relatively bulky –N(CH3)(C6H11) segment are longer than those formed by the tert-C4H9NH– and –NHCH2C(CH3)2CH2NH– segments. For example, we note the P—N bond in structure (IV), made by the –N(CH3)(C6H11) and –NHCH2C(CH3)2CH2NH— segments is 1.6672 (18) Å for the former and 1.6440 (18) and 1.628 (2) Å for the latter.
Moreover, among the nine molecules in the three structures including both –N(CH3)(C6H11) and –NHC6H11 segments, for eight of the molecules, longer P—N bonds were found involving –N(CH3)(C6H11). For example, note P1—N3 = 1.6405 (16) Å and P1—N11 1.6300 (16) Å involving the –N(CH3)(C6H11) and C6H11NH– segments, respectively in (II). On the other hand, in one of the independent molecules of (III), a shorter P—N bond [1.650 (4) Å] was found made by –N(CH3)(C6H11) in comparison with the two C6H11NH– segments [1.680 (6) and 1.655 (7) Å]. [bond lengths don't match Table 4]
Surprisingly, in (II), the 4-CH3—C6H4NH– segment makes a longer P—N bond with respect to the –N(CH3)(C6H11) segment, which is attributed to the different hybridization states of the C atoms attached to the N atoms in these groups (sp2 and sp3, respectively), resulting in an electron-withdrawing effect of the aromatic ring. This is similar to what was reported previously for the P—N bonds made by the same groups in rac-(C6H5O)P(O)[N(CH3)(cyclo-C6H11)][NH(C6H4-p-CH3)] (Pourayoubi et al., 2013).
In some molecules of structures (I)–(IV), the C—N—C angles of the –N(CH3)(C6H11) segments are smaller than the two related P—N—C angles; however, there are also the cases where the C—N—C angle is larger than one of the P—N—C angles at the same N atom. For example, in one of the molecules in structure (II), the C—N—C and two P—N—C angles are 118.96 (16), 121.69 (13) and 118.38 (14)°, respectively.
The extended structure of (I) includes four independent molecules in a one-dimensional chain aggregation (Fig. 5). In this chain, adjacent molecules are linked via (N—H···)2O═P and (N—H···)O═P hydrogen bonds along [001], building two different and two different C(4) motifs with an C(4)C(4) arrangement (Table 6).
In the crystal packing of (II), each P═O group takes part with two N—H units in intermolecular (N—H···)2O═P hydrogen bonds, forming three different rings in a one-dimensional chain containing three independent molecules, running along [100] (Fig. 6 and Table 7).
The hydrogen-bond pattern of (III) is similar to that of (II), with adjacent molecules linked through (N—H···)2O═P hydrogen bonds in a one-dimensional chain along [010], with building motifs (Fig. 7 and Table 8).
The crystal packing of (IV) is slightly different, with molecules connected through (N—H···)(N—H···)O═P hydrogen bonds, forming ring motifs, into extended chains parallel to [100] (Fig. 8 and Table 9).
According to the hydrogen-bond patterns discussed, (N—H···)2O═P and (N—H···)(N—H···)O═P refer to the double-acceptor action of O atoms. The former notation was used when two N—H groups belong to one molecule (in a ring motif) and the latter is used for the case with two N—H groups belonging to individual molecules (forming a ring motif). On the other hand, the structure of (I) also includes a two-centred hydrogen bond, forming a C(4) motif, and there are some N—H groups which are not involved in hydrogen-bond interactions.
The starting phosphorus–chlorine compound Cl2P(O)[N(CH3)(C6H11)] was synthesized at 273 K by the reaction of NH(CH3)(C6H11) (20 mmol) dissolved in dry acetonitrile (10 ml) with a solution of P(O)Cl3 (10 mmol) in the same solvent (20 ml). After stirring for 5 h, the solid which formed, i.e. (C6H11)(CH3)NH·HCl, was filtered off. The acetonitrile solution of Cl2P(O)[N(CH3)(C6H11)] was used for the next step. The other starting compound, i.e. rac-ClP(O)[N(CH3)(C6H11)](NHC6H11) was synthesized from Cl2P(O)[N(CH3)(C6H11)] using the same procedure, but using Cl2P(O)[N(CH3)(C6H11)] as the starting phosphorus–chlorine compound in the reaction with NH2(C6H11).
For the synthesis of (I), a solution of tert-butylamine (4 mmol) in dry acetonitrile (10 ml) was added to a solution of ClP(O)[N(CH3)(C6H11)](NHC6H11) (2 mmol) in the same solvent (20 ml) at 273 K. After stirring for 7 h, the solvent was removed in vacuo and the solid obtained was washed with distilled water.
Compound (II) was synthesized following the same procedure but by using a mixture of p-toluidine and triethylamine (2 mmol of each) instead of tert-butylamine. Colourless single crystals suitable for X-ray diffraction experiments were obtained at room temperature from CH3OH/CHCl3/DMF (4:4:1 v/v/v) for (I) and from CHCl3/C2H5OH (4:1 v/v) for (II).
For the synthesis of (III), a solution of cyclohexylamine (8 mmol) in dry acetonitrile (10 ml) was added to a solution of Cl2P(O)[N(CH3)(C6H11)] (2 mmol) in the same solvent (20 ml) at 273 K. After stirring for 4 h, the solvent was removed in vacuo and the solid obtained was washed with distilled water.
Compound (IV) was obtained using a similar procedure as for (III), but using 2,2-dimethylpropane-1,3-diamine (4 mmol) instead of cyclohexylamine. Colourless single crystals suitable for X-ray diffraction experiments were obtained at room temperature from CHCl3/C2H5OH (2:2 v/v) for (III) and from CH3OH/DMF (4:1 v/v) for (IV). The 1H NMR, 13C NMR and MS spectra of compounds (I)–(IV) are given in Figs. S1–S15 in the Supporting information.
Cl2P(O)[N(CH3)(cyclo-C6H11)] was synthesized from the reaction between Cl3P(O) and N-methylcyclohexylamine (1:2 molar ratio). Racemic ClP(O)[N(CH3)(cyclo-C6H11)][NH(cyclo-C6H11)] was then prepared from Cl2P(O)[N(CH3)(cyclo-C6H11)]and cyclohexylamine (1:2 molar ratio), for the first time. In each reaction, the corresponding amine acts as both a nucleophile and an HCl scavenger.
Acetonitrile was found to be a suitable solvent in these reactions, due to the low solubility of the [(cyclo-C6H11)NH2(CH3)]Cl (first reaction) and [(cyclo-C6H11)NH3]Cl (second reaction) salts and the good solubility of Cl2P(O)[N(CH3)(cyclo-C6H11)] and ClP(O)[N(CH3)(cyclo-C6H11)][NH(cyclo-C6H11)]. Thus, the salts formed in each reaction were simply filtered off and the pure products Cl2P(O)[N(CH3)(cyclo-C6H11)] and ClP(O)[N(CH3)(cyclo-C6H11)][NH(cyclo-C6H11)] remained in the acetonitrile solution.
In the final step, for the preparation of (I) and (II) (see Scheme 2), rac-ClP(O)[N(CH3)(cyclo-C6H11)][NH(cyclo-C6H11)] reacts with the corresponding amine [2 eqivalents of tert-butylamine for (I) and an equimolar mixture of p-toluidine and triethylamine for (II)] to yield the racemic (RNH)P(O)[N(CH3)(cyclo-C6H11)][NH(cyclo-C6H11)] mixed phosphoric triamides [R = t-Bu in (I) and 4-CH3—C6H4 in (II)], and the [tBuNH3]Cl salt for (I) and 4-CH3—C6H4NH3Cl for (II)) were removed by dissolving in H2O.
The phosphoric triamides (III) and (IV) were prepared from the reaction between an acetonitrile solution of Cl2P(O)[N(CH3)(cyclo-C6H11)] and the corresponding amine. The salts which formed were removed with H2O (see Scheme 2).
Crystal data, data collection and structure refinement details are summarized in Table 1. Non-H atoms were refined anisotropically. H atoms were all located in the difference Fourier maps for each of the title structures, but those attached to C atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularize their geometry (C—H in the range 0.92 – 1.00 Å de pending on hybridization state), after which the positions of H-atoms not involved in hydrogen bonding interactions were refined with riding constraints (Cooper et al., 2010) and fixed isotropic displacement parameters Uiso(H) = 1.5Ueq(Ci) for CH3 groups or 1.2Ueq(Cii) for CH2 and CH groups, where Ueq(Ci) and Ueq(Cii) are the equivalent displacement parameters of the C atoms to which corresponding H atoms are bonded. The H atoms of the NH groups were allowed to refine with a restrained N—H bond distance of 0.86 (2) Å and Uiso(H) = 1.2Ueq(N). The H atoms of the NH groups were refined using soft distance and angle restraints.
In (I), the absolute configuration was arbitrarily assigned. One independent molecule of (I) appeared to be heavily disordered. This disorder was modelled with split positions. Two orientations of tert-butyl were found, and they were restrained to have a similar geometry. In addition restraints were used in order to keep reasonable C—C sp3-sp3 bond distances. The anisotropic atomic displacement parameters of adjacent atoms in the disordered fragment were restrained to be the same (Betteridge et al., 2003). The similarity restraint was not used for the two disordered parts of the cyclohexane group of the same molecule. Instead, only the anisotropic atomic displacement parameters of adjacent atoms were restrained to be the same, and restraints were used in order to keep reasonable C—C sp3-sp3 bond distances within the rings. The occupancies of the two parts for tert-butyl and cyclohexane were refined to 0.233 (9)/0.767 (9) and 0.443 (11)/0.557 (9), respectively.
In (III), disorder on all six-membered rings appeared to be impossible to model satisfactorily using split positions. For this reason restraints on angles and distances were used in order to get an acceptable geometry. It was in addition necessary to use thermal similarity restraints on all atoms within the rings.
Although the general structural features are certainly correct in (I) and (III), some caution is necessary when interpreting the fine structural details in especially the disordered parts.
Data collection: GEMINI (Oxford Diffraction, 2006) for (I), (III); CrysAlis PRO (Agilent, 2011) for (II), (IV). For all compounds, cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011). Program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007) for (I), (III); SUPERFLIP (Palatinus & Chapuis, 2007) for (II), (IV). For all compounds, program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003) and enCIFer (Allen et al., 2004).
C17H36N3OP | F(000) = 1456.000 |
Mr = 329.45 | Dx = 1.114 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.9879 (4) Å | Cell parameters from 12452 reflections |
b = 19.1972 (6) Å | θ = 1.7–27.2° |
c = 17.0720 (6) Å | µ = 0.15 mm−1 |
β = 90.542 (3)° | T = 175 K |
V = 3928.67 (14) Å3 | 0.45 × 0.35 × 0.30 mm |
Z = 8 |
Oxford Diffraction Gemini diffractometer | 14523 reflections with I > 2.0σ(I) |
Graphite monochromator | Rint = 0.064 |
ω scans | θmax = 29.3°, θmin = 1.6° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | h = −15→15 |
Tmin = 0.95, Tmax = 0.96 | k = −26→25 |
43414 measured reflections | l = −23→22 |
18366 independent reflections |
Refinement on F2 | Hydrogen site location: difference Fourier map |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.096 | Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)2]2 Ai are: 419. 494. 196. |
wR(F2) = 0.118 | (Δ/σ)max = 0.009 |
S = 1.09 | Δρmax = 1.77 e Å−3 |
17831 reflections | Δρmin = −0.83 e Å−3 |
883 parameters | Absolute structure: Flack (1983), 9230 Friedel pairs |
141 restraints | Absolute structure parameter: −0.08 (10) |
Primary atom site location: other |
C17H36N3OP | V = 3928.67 (14) Å3 |
Mr = 329.45 | Z = 8 |
Monoclinic, P21 | Mo Kα radiation |
a = 11.9879 (4) Å | µ = 0.15 mm−1 |
b = 19.1972 (6) Å | T = 175 K |
c = 17.0720 (6) Å | 0.45 × 0.35 × 0.30 mm |
β = 90.542 (3)° |
Oxford Diffraction Gemini diffractometer | 18366 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | 14523 reflections with I > 2.0σ(I) |
Tmin = 0.95, Tmax = 0.96 | Rint = 0.064 |
43414 measured reflections |
R[F2 > 2σ(F2)] = 0.096 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.118 | Δρmax = 1.77 e Å−3 |
S = 1.09 | Δρmin = −0.83 e Å−3 |
17831 reflections | Absolute structure: Flack (1983), 9230 Friedel pairs |
883 parameters | Absolute structure parameter: −0.08 (10) |
141 restraints |
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1 K. Cosier, J. & Glazer, A·M., 1986. J. Appl. Cryst. 105–107. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
P101 | 0.86815 (10) | 0.94106 (9) | 0.24530 (7) | 0.0408 | |
O102 | 0.7937 (3) | 0.9650 (2) | 0.30906 (19) | 0.0536 | |
N103 | 0.9881 (3) | 0.9840 (2) | 0.2551 (2) | 0.0441 | |
C104 | 0.9918 (5) | 1.0510 (3) | 0.2919 (4) | 0.0719 | |
H1041 | 0.9916 | 1.0883 | 0.2550 | 0.0969* | |
H1042 | 0.9294 | 1.0562 | 0.3254 | 0.0969* | |
H1043 | 1.0580 | 1.0533 | 0.3232 | 0.0971* | |
C105 | 1.0827 (3) | 0.9655 (3) | 0.2013 (3) | 0.0375 | |
H1051 | 1.0695 | 0.9186 | 0.1832 | 0.0421* | |
C106 | 1.0886 (4) | 1.0124 (3) | 0.1305 (3) | 0.0576 | |
H1061 | 1.1028 | 1.0599 | 0.1461 | 0.0618* | |
H1062 | 1.0179 | 1.0119 | 0.1028 | 0.0618* | |
C107 | 1.1837 (5) | 0.9866 (4) | 0.0760 (3) | 0.0735 | |
H1071 | 1.1681 | 0.9395 | 0.0594 | 0.0846* | |
H1072 | 1.1872 | 1.0166 | 0.0314 | 0.0850* | |
C108 | 1.2923 (5) | 0.9870 (4) | 0.1187 (4) | 0.0891 | |
H1081 | 1.3097 | 1.0346 | 0.1330 | 0.1067* | |
H1082 | 1.3491 | 0.9693 | 0.0847 | 0.1070* | |
C109 | 1.2873 (4) | 0.9414 (4) | 0.1898 (4) | 0.0739 | |
H1091 | 1.2735 | 0.8934 | 0.1747 | 0.0869* | |
H1092 | 1.3574 | 0.9439 | 0.2172 | 0.0873* | |
C110 | 1.1924 (4) | 0.9668 (3) | 0.2459 (3) | 0.0529 | |
H1101 | 1.2077 | 1.0131 | 0.2649 | 0.0599* | |
H1102 | 1.1857 | 0.9346 | 0.2894 | 0.0598* | |
N111 | 0.8095 (3) | 0.9479 (2) | 0.1595 (2) | 0.0443 | |
H1111 | 0.841 (3) | 0.9256 (19) | 0.1239 (10) | 0.0501* | |
C112 | 0.7273 (5) | 0.9985 (3) | 0.1331 (3) | 0.0559 | |
C113 | 0.7262 (6) | 1.0005 (4) | 0.0439 (3) | 0.0776 | |
H1131 | 0.7116 | 0.9557 | 0.0221 | 0.1087* | |
H1132 | 0.7981 | 1.0169 | 0.0294 | 0.1091* | |
H1133 | 0.6709 | 1.0329 | 0.0264 | 0.1088* | |
C114 | 0.6094 (5) | 0.9799 (5) | 0.1599 (4) | 0.0920 | |
H1141 | 0.5920 | 0.9336 | 0.1420 | 0.1227* | |
H1142 | 0.5568 | 1.0126 | 0.1390 | 0.1228* | |
H1143 | 0.6088 | 0.9812 | 0.2163 | 0.1227* | |
C115 | 0.7566 (6) | 1.0719 (4) | 0.1629 (4) | 0.0775 | |
H1151 | 0.7541 | 1.0731 | 0.2192 | 0.1137* | |
H1152 | 0.7045 | 1.1049 | 0.1410 | 0.1141* | |
H1153 | 0.8306 | 1.0822 | 0.1454 | 0.1138* | |
N116 | 0.9027 (4) | 0.8601 (3) | 0.2464 (2) | 0.0479 | |
H1161 | 0.884 (3) | 0.8385 (11) | 0.2058 (16) | 0.0621* | |
C117 | 0.9836 (4) | 0.8242 (3) | 0.2939 (3) | 0.0467 | |
H1171 | 1.0571 | 0.8426 | 0.2798 | 0.0541* | |
C118 | 0.9672 (6) | 0.8376 (3) | 0.3815 (3) | 0.0701 | |
H1811 | 0.9733 | 0.8873 | 0.3894 | 0.0787* | |
H1182 | 0.8942 | 0.8222 | 0.3978 | 0.0790* | |
C119 | 1.0538 (6) | 0.8015 (3) | 0.4307 (4) | 0.0717 | |
H1191 | 1.1258 | 0.8212 | 0.4180 | 0.0877* | |
H1192 | 1.0392 | 0.8094 | 0.4855 | 0.0882* | |
C120 | 1.0604 (6) | 0.7256 (4) | 0.4164 (4) | 0.0763 | |
H1201 | 1.1222 | 0.7051 | 0.4450 | 0.0838* | |
H1202 | 0.9912 | 0.7056 | 0.4342 | 0.0840* | |
C121 | 1.0732 (6) | 0.7092 (4) | 0.3278 (4) | 0.0754 | |
H1211 | 1.1465 | 0.7239 | 0.3101 | 0.0860* | |
H1212 | 1.0645 | 0.6593 | 0.3201 | 0.0859* | |
C122 | 0.9885 (5) | 0.7481 (3) | 0.2798 (4) | 0.0667 | |
H1221 | 1.0056 | 0.7396 | 0.2251 | 0.0761* | |
H1223 | 0.9152 | 0.7296 | 0.2923 | 0.0759* | |
P201 | 0.36355 (12) | 0.30472 (9) | 0.25482 (8) | 0.0464 | |
O202 | 0.2851 (3) | 0.2863 (2) | 0.1898 (2) | 0.0606 | |
N203 | 0.4854 (4) | 0.2623 (3) | 0.2390 (2) | 0.0530 | |
C204 | 0.4823 (5) | 0.1981 (3) | 0.1939 (4) | 0.0748 | |
H2041 | 0.4089 | 0.1915 | 0.1726 | 0.1019* | |
H2042 | 0.5029 | 0.1598 | 0.2266 | 0.1020* | |
H2043 | 0.5329 | 0.2028 | 0.1516 | 0.1018* | |
C205 | 0.5771 (4) | 0.2708 (3) | 0.2938 (2) | 0.0355 | |
H2051 | 0.5665 | 0.3152 | 0.3188 | 0.0402* | |
C206 | 0.6892 (4) | 0.2742 (4) | 0.2524 (3) | 0.0610 | |
H2061 | 0.7013 | 0.2292 | 0.2261 | 0.0651* | |
H2062 | 0.6880 | 0.3109 | 0.2137 | 0.0653* | |
C207 | 0.7838 (5) | 0.2869 (4) | 0.3097 (4) | 0.0793 | |
H2071 | 0.8539 | 0.2887 | 0.2809 | 0.0878* | |
H2072 | 0.7725 | 0.3309 | 0.3365 | 0.0879* | |
C208 | 0.7921 (4) | 0.2288 (4) | 0.3703 (3) | 0.0762 | |
H2081 | 0.8521 | 0.2379 | 0.4071 | 0.0927* | |
H2082 | 0.8046 | 0.1843 | 0.3451 | 0.0932* | |
C209 | 0.6788 (5) | 0.2254 (5) | 0.4145 (4) | 0.1040 | |
H2091 | 0.6689 | 0.2717 | 0.4383 | 0.1210* | |
H2092 | 0.6810 | 0.1901 | 0.4551 | 0.1211* | |
C210 | 0.5837 (5) | 0.2130 (4) | 0.3574 (4) | 0.0716 | |
H2101 | 0.5968 | 0.1686 | 0.3312 | 0.0808* | |
H2102 | 0.5133 | 0.2118 | 0.3856 | 0.0809* | |
N211 | 0.3118 (3) | 0.2907 (2) | 0.3391 (2) | 0.0459 | |
H2111 | 0.344 (3) | 0.3120 (19) | 0.3765 (9) | 0.0539* | |
C212 | 0.2305 (4) | 0.2358 (3) | 0.3630 (3) | 0.0543 | |
C214 | 0.1102 (4) | 0.2556 (4) | 0.3346 (4) | 0.0626 | |
H2141 | 0.0870 | 0.2978 | 0.3603 | 0.0909* | |
H2142 | 0.0622 | 0.2177 | 0.3476 | 0.0909* | |
H2143 | 0.1105 | 0.2630 | 0.2794 | 0.0911* | |
C213 | 0.2290 (5) | 0.2328 (3) | 0.4521 (3) | 0.0631 | |
H2131 | 0.2988 | 0.2168 | 0.4706 | 0.0887* | |
H2132 | 0.2147 | 0.2780 | 0.4729 | 0.0884* | |
H2133 | 0.1727 | 0.2013 | 0.4697 | 0.0889* | |
C215 | 0.2577 (5) | 0.1677 (3) | 0.3287 (4) | 0.0717 | |
H2151 | 0.3319 | 0.1559 | 0.3431 | 0.1031* | |
H2152 | 0.2065 | 0.1333 | 0.3473 | 0.1028* | |
H2153 | 0.2512 | 0.1707 | 0.2730 | 0.1028* | |
N216 | 0.3992 (3) | 0.3857 (2) | 0.2622 (2) | 0.0472 | |
H2161 | 0.425 (2) | 0.3896 (12) | 0.3081 (10) | 0.0615* | |
C217 | 0.4758 (4) | 0.4227 (3) | 0.2139 (3) | 0.0543 | |
H2171 | 0.5504 | 0.4049 | 0.2283 | 0.0602* | |
C218 | 0.4569 (6) | 0.4097 (3) | 0.1266 (3) | 0.0698 | |
H2182 | 0.3820 | 0.4242 | 0.1122 | 0.0829* | |
H2181 | 0.4663 | 0.3601 | 0.1165 | 0.0827* | |
C219 | 0.5386 (6) | 0.4498 (4) | 0.0780 (4) | 0.0875 | |
H2191 | 0.6130 | 0.4304 | 0.0879 | 0.0960* | |
H2192 | 0.5185 | 0.4434 | 0.0231 | 0.0962* | |
C220 | 0.5390 (7) | 0.5251 (4) | 0.0950 (4) | 0.0914 | |
H2201 | 0.5985 | 0.5471 | 0.0660 | 0.1009* | |
H2202 | 0.4680 | 0.5443 | 0.0788 | 0.1011* | |
C221 | 0.5600 (6) | 0.5403 (4) | 0.1810 (4) | 0.0865 | |
H2211 | 0.5509 | 0.5904 | 0.1913 | 0.0960* | |
H2212 | 0.6364 | 0.5264 | 0.1944 | 0.0961* | |
C222 | 0.4757 (5) | 0.4987 (3) | 0.2314 (4) | 0.0700 | |
H2221 | 0.4944 | 0.5077 | 0.2862 | 0.0776* | |
H2222 | 0.4005 | 0.5161 | 0.2192 | 0.0773* | |
P301 | 0.09668 (10) | 0.32332 (9) | 0.02250 (7) | 0.0381 | |
O302 | 0.0704 (3) | 0.3599 (2) | −0.0514 (2) | 0.0560 | |
N303 | −0.0048 (3) | 0.2667 (2) | 0.0372 (2) | 0.0454 | |
C304 | −0.0020 (4) | 0.2238 (3) | 0.1079 (3) | 0.0545 | |
H3041 | 0.0683 | 0.2287 | 0.1327 | 0.0772* | |
H3042 | −0.0147 | 0.1761 | 0.0954 | 0.0771* | |
H3043 | −0.0583 | 0.2399 | 0.1429 | 0.0774* | |
C305 | −0.1035 (4) | 0.2606 (3) | −0.0135 (3) | 0.0532 | |
H3051 | −0.0939 | 0.2934 | −0.0566 | 0.0577* | |
C306 | −0.2113 (4) | 0.2821 (3) | 0.0285 (4) | 0.0625 | |
H3061 | −0.2231 | 0.2505 | 0.0722 | 0.0692* | |
H3062 | −0.2065 | 0.3298 | 0.0479 | 0.0688* | |
C307 | −0.3118 (5) | 0.2757 (4) | −0.0273 (4) | 0.0783 | |
H3071 | −0.3783 | 0.2860 | 0.0017 | 0.0902* | |
H3072 | −0.3048 | 0.3090 | −0.0700 | 0.0899* | |
C308 | −0.3227 (5) | 0.2043 (4) | −0.0614 (4) | 0.0739 | |
H3081 | −0.3355 | 0.1721 | −0.0198 | 0.0859* | |
H3082 | −0.3847 | 0.2032 | −0.0971 | 0.0860* | |
C309 | −0.2156 (6) | 0.1841 (4) | −0.1035 (4) | 0.0905 | |
H3091 | −0.2213 | 0.1366 | −0.1211 | 0.1052* | |
H3092 | −0.2039 | 0.2148 | −0.1478 | 0.1050* | |
C310 | −0.1173 (5) | 0.1897 (4) | −0.0474 (4) | 0.0712 | |
H3101 | −0.1270 | 0.1557 | −0.0061 | 0.0826* | |
H3102 | −0.0517 | 0.1781 | −0.0763 | 0.0833* | |
N311 | 0.2173 (3) | 0.2837 (2) | 0.0255 (2) | 0.0545 | |
H3111 | 0.240 (2) | 0.2765 (17) | 0.0725 (10) | 0.0592* | |
C312 | 0.2608 (3) | 0.2321 (2) | −0.0278 (2) | 0.0617 | |
C3131 | 0.3317 (19) | 0.1831 (9) | 0.0203 (5) | 0.0922 | 0.233 (8) |
H3132 | 0.3358 | 0.1386 | −0.0051 | 0.1238* | 0.233 (8) |
H3133 | 0.4057 | 0.2011 | 0.0282 | 0.1238* | 0.233 (8) |
H3134 | 0.2960 | 0.1779 | 0.0701 | 0.1238* | 0.233 (8) |
C3132 | 0.2256 (7) | 0.1620 (3) | 0.0030 (4) | 0.0844 | 0.767 (8) |
H3135 | 0.2535 | 0.1264 | −0.0301 | 0.1169* | 0.767 (8) |
H3136 | 0.2542 | 0.1557 | 0.0546 | 0.1169* | 0.767 (8) |
H3137 | 0.1465 | 0.1599 | 0.0037 | 0.1169* | 0.767 (8) |
C3141 | 0.1796 (7) | 0.1856 (9) | −0.0649 (11) | 0.0941 | 0.233 (8) |
H3142 | 0.2156 | 0.1532 | −0.0983 | 0.1216* | 0.233 (8) |
H3143 | 0.1343 | 0.2160 | −0.0955 | 0.1216* | 0.233 (8) |
H3144 | 0.1345 | 0.1612 | −0.0287 | 0.1216* | 0.233 (8) |
C3142 | 0.2151 (5) | 0.2324 (4) | −0.1076 (4) | 0.0804 | 0.767 (8) |
H3145 | 0.2078 | 0.1859 | −0.1278 | 0.1133* | 0.767 (8) |
H3146 | 0.2630 | 0.2589 | −0.1411 | 0.1133* | 0.767 (8) |
H3147 | 0.1429 | 0.2540 | −0.1060 | 0.1133* | 0.767 (8) |
C3151 | 0.3332 (19) | 0.2700 (5) | −0.0877 (10) | 0.1255 | 0.233 (8) |
H3152 | 0.4088 | 0.2546 | −0.0808 | 0.1751* | 0.233 (8) |
H3153 | 0.3293 | 0.3193 | −0.0789 | 0.1751* | 0.233 (8) |
H3154 | 0.3087 | 0.2599 | −0.1402 | 0.1751* | 0.233 (8) |
C3152 | 0.3865 (5) | 0.2377 (4) | −0.0263 (4) | 0.1054 | 0.767 (8) |
H3155 | 0.4187 | 0.2046 | −0.0607 | 0.1768* | 0.767 (8) |
H3156 | 0.4063 | 0.2834 | −0.0426 | 0.1768* | 0.767 (8) |
H3157 | 0.4134 | 0.2300 | 0.0255 | 0.1768* | 0.767 (8) |
N316 | 0.1110 (3) | 0.3734 (2) | 0.0984 (2) | 0.0474 | |
H3161 | 0.155 (3) | 0.3577 (15) | 0.1338 (12) | 0.0543* | |
C317 | 0.0261 (5) | 0.4224 (3) | 0.1250 (3) | 0.0577 | |
C3182 | 0.0087 (17) | 0.4132 (12) | 0.2113 (7) | 0.1051 | 0.443 (9) |
C3181 | −0.0517 (12) | 0.4045 (8) | 0.1883 (9) | 0.1026 | 0.557 (9) |
H3182 | −0.0112 | 0.3944 | 0.2350 | 0.1100* | 0.557 (9) |
H3183 | −0.0906 | 0.3640 | 0.1714 | 0.1100* | 0.557 (9) |
H3184 | 0.0764 | 0.4240 | 0.2380 | 0.1110* | 0.443 (9) |
H3185 | −0.0089 | 0.3655 | 0.2192 | 0.1150* | 0.443 (9) |
C3191 | −0.1351 (10) | 0.4608 (6) | 0.1996 (10) | 0.0880 | 0.557 (9) |
H3192 | −0.1800 | 0.4447 | 0.2415 | 0.1193* | 0.557 (9) |
H3193 | −0.1808 | 0.4690 | 0.1548 | 0.1193* | 0.557 (9) |
H3194 | −0.0754 | 0.4504 | 0.3064 | 0.1136* | 0.443 (9) |
C3192 | −0.0815 (16) | 0.4529 (6) | 0.2510 (9) | 0.0839 | 0.443 (9) |
H3195 | −0.1514 | 0.4343 | 0.2346 | 0.1136* | 0.443 (9) |
C320 | −0.0781 (6) | 0.5267 (4) | 0.2245 (4) | 0.0877 | |
H3201 | −0.1333 | 0.5616 | 0.2314 | 0.0975* | 0.557 (9) |
H3202 | −0.0390 | 0.5197 | 0.2725 | 0.0975* | 0.557 (9) |
H3203 | −0.1410 | 0.5512 | 0.2438 | 0.0975* | 0.443 (9) |
H3204 | −0.0117 | 0.5475 | 0.2445 | 0.0975* | 0.443 (9) |
C3211 | 0.0034 (13) | 0.5504 (6) | 0.1656 (10) | 0.1062 | 0.557 (9) |
H3212 | 0.0398 | 0.5915 | 0.1835 | 0.1187* | 0.557 (9) |
H3213 | −0.0364 | 0.5603 | 0.1185 | 0.1187* | 0.557 (9) |
C3212 | −0.0856 (15) | 0.5255 (11) | 0.1357 (6) | 0.1020 | 0.443 (9) |
H3214 | −0.0769 | 0.5723 | 0.1187 | 0.1249* | 0.443 (9) |
H3215 | −0.1544 | 0.5076 | 0.1164 | 0.1249* | 0.443 (9) |
C3221 | 0.0810 (9) | 0.4906 (5) | 0.1497 (9) | 0.0799 | 0.557 (9) |
H3222 | 0.1274 | 0.5054 | 0.1081 | 0.0970* | 0.557 (9) |
H3223 | 0.1252 | 0.4828 | 0.1954 | 0.0970* | 0.557 (9) |
C3222 | 0.0114 (15) | 0.4927 (7) | 0.0947 (11) | 0.0918 | 0.443 (9) |
H3224 | 0.0790 | 0.5160 | 0.1076 | 0.1205* | 0.443 (9) |
H3225 | 0.0027 | 0.4906 | 0.0394 | 0.1205* | 0.443 (9) |
P401 | 0.61608 (9) | 0.92741 (8) | 0.48006 (6) | 0.0310 | |
O402 | 0.5975 (3) | 0.89586 (19) | 0.55880 (18) | 0.0436 | |
N403 | 0.5062 (3) | 0.9748 (2) | 0.4578 (2) | 0.0417 | |
C404 | 0.5087 (4) | 1.0179 (3) | 0.3879 (3) | 0.0532 | |
H4041 | 0.4360 | 1.0282 | 0.3689 | 0.0745* | |
H4042 | 0.5440 | 1.0607 | 0.3994 | 0.0742* | |
H4043 | 0.5492 | 0.9939 | 0.3496 | 0.0741* | |
C405 | 0.4086 (4) | 0.9844 (3) | 0.5103 (3) | 0.0461 | |
H4051 | 0.4199 | 0.9540 | 0.5547 | 0.0521* | |
C406 | 0.3997 (4) | 1.0583 (3) | 0.5393 (4) | 0.0600 | |
H4061 | 0.3869 | 1.0885 | 0.4956 | 0.0719* | |
H4062 | 0.4665 | 1.0724 | 0.5659 | 0.0720* | |
C407 | 0.2988 (5) | 1.0653 (5) | 0.5966 (4) | 0.0918 | |
H4071 | 0.3122 | 1.0350 | 0.6405 | 0.1090* | |
H4072 | 0.2920 | 1.1132 | 0.6143 | 0.1089* | |
C408 | 0.1938 (4) | 1.0416 (4) | 0.5579 (4) | 0.0666 | |
H4081 | 0.1769 | 1.0724 | 0.5157 | 0.0788* | |
H4082 | 0.1349 | 1.0438 | 0.5956 | 0.0794* | |
C409 | 0.2033 (5) | 0.9685 (4) | 0.5282 (4) | 0.0789 | |
H4091 | 0.1357 | 0.9569 | 0.4988 | 0.0936* | |
H4092 | 0.2128 | 0.9369 | 0.5719 | 0.0939* | |
C410 | 0.3018 (4) | 0.9613 (3) | 0.4717 (4) | 0.0584 | |
H4101 | 0.3089 | 0.9131 | 0.4560 | 0.0689* | |
H4102 | 0.2887 | 0.9904 | 0.4261 | 0.0689* | |
N411 | 0.7324 (3) | 0.9710 (3) | 0.4737 (2) | 0.0468 | |
H4111 | 0.752 (3) | 0.981 (2) | 0.4272 (10) | 0.0517* | |
C412 | 0.7965 (4) | 1.0050 (3) | 0.5355 (3) | 0.0450 | |
C413 | 0.8877 (5) | 1.0498 (3) | 0.4961 (3) | 0.0626 | |
H4131 | 0.9341 | 1.0203 | 0.4645 | 0.0879* | |
H4132 | 0.9328 | 1.0720 | 0.5361 | 0.0873* | |
H4133 | 0.8528 | 1.0848 | 0.4632 | 0.0878* | |
C414 | 0.7255 (5) | 1.0500 (4) | 0.5878 (4) | 0.0730 | |
H4141 | 0.6944 | 1.0882 | 0.5579 | 0.1057* | |
H4142 | 0.7724 | 1.0685 | 0.6282 | 0.1060* | |
H4143 | 0.6683 | 1.0229 | 0.6107 | 0.1058* | |
C415 | 0.8564 (5) | 0.9508 (4) | 0.5845 (4) | 0.0788 | |
H4151 | 0.9039 | 0.9732 | 0.6233 | 0.1119* | |
H4152 | 0.8005 | 0.9233 | 0.6097 | 0.1119* | |
H4153 | 0.9006 | 0.9213 | 0.5512 | 0.1122* | |
N416 | 0.6322 (3) | 0.8731 (2) | 0.4070 (2) | 0.0402 | |
H4161 | 0.6940 (17) | 0.8732 (19) | 0.3845 (17) | 0.0464* | |
C417 | 0.5442 (4) | 0.8346 (3) | 0.3689 (3) | 0.0493 | |
H4171 | 0.4903 | 0.8682 | 0.3496 | 0.0547* | |
C418 | 0.5920 (6) | 0.7965 (4) | 0.2966 (4) | 0.1023 | |
H4181 | 0.6263 | 0.8304 | 0.2621 | 0.1039* | |
H4182 | 0.6464 | 0.7624 | 0.3147 | 0.1040* | |
C419 | 0.4971 (7) | 0.7590 (5) | 0.2519 (4) | 0.1057 | |
H4191 | 0.4457 | 0.7952 | 0.2332 | 0.1197* | |
H4192 | 0.5282 | 0.7332 | 0.2087 | 0.1200* | |
C420 | 0.4350 (6) | 0.7115 (4) | 0.3024 (5) | 0.0810 | |
H4201 | 0.4833 | 0.6737 | 0.3185 | 0.0919* | |
H4202 | 0.3725 | 0.6934 | 0.2739 | 0.0918* | |
C421 | 0.3951 (7) | 0.7478 (5) | 0.3730 (5) | 0.1161 | |
H4211 | 0.3377 | 0.7804 | 0.3580 | 0.1361* | |
H4212 | 0.3650 | 0.7128 | 0.4079 | 0.1356* | |
C422 | 0.4867 (6) | 0.7858 (4) | 0.4186 (4) | 0.0813 | |
H4221 | 0.4545 | 0.8107 | 0.4623 | 0.1009* | |
H4222 | 0.5405 | 0.7521 | 0.4385 | 0.1009* | |
H3171 | −0.0160 | 0.4335 | 0.0792 | 0.0622* | 0.557 (9) |
H3172 | −0.0378 | 0.4011 | 0.1019 | 0.0622* | 0.443 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
P101 | 0.0352 (6) | 0.0506 (9) | 0.0367 (6) | −0.0070 (6) | 0.0093 (5) | −0.0016 (6) |
O102 | 0.0399 (19) | 0.083 (3) | 0.0379 (19) | −0.0087 (19) | 0.0166 (15) | −0.0070 (19) |
N103 | 0.040 (2) | 0.056 (3) | 0.037 (2) | −0.0121 (19) | 0.0102 (18) | −0.017 (2) |
C104 | 0.055 (4) | 0.073 (5) | 0.088 (5) | −0.024 (3) | 0.033 (3) | −0.031 (4) |
C105 | 0.029 (2) | 0.050 (3) | 0.034 (2) | −0.008 (2) | 0.0084 (19) | −0.008 (2) |
C106 | 0.032 (3) | 0.087 (5) | 0.054 (3) | −0.008 (3) | 0.010 (2) | 0.003 (3) |
C107 | 0.062 (4) | 0.113 (6) | 0.047 (3) | −0.001 (4) | 0.025 (3) | 0.018 (4) |
C108 | 0.043 (4) | 0.146 (8) | 0.079 (5) | −0.015 (4) | 0.035 (3) | 0.000 (5) |
C109 | 0.034 (3) | 0.111 (6) | 0.076 (4) | 0.008 (4) | −0.004 (3) | −0.025 (4) |
C110 | 0.042 (3) | 0.066 (4) | 0.050 (3) | −0.007 (3) | 0.006 (2) | −0.008 (3) |
N111 | 0.034 (2) | 0.061 (3) | 0.0377 (17) | 0.004 (2) | 0.0121 (14) | −0.003 (2) |
C112 | 0.044 (3) | 0.074 (4) | 0.050 (3) | 0.014 (3) | 0.013 (3) | 0.003 (3) |
C113 | 0.089 (5) | 0.099 (6) | 0.045 (4) | 0.024 (4) | 0.004 (3) | 0.010 (4) |
C114 | 0.044 (4) | 0.167 (9) | 0.065 (4) | 0.002 (4) | 0.019 (3) | 0.008 (5) |
C115 | 0.068 (4) | 0.079 (5) | 0.085 (5) | 0.016 (4) | −0.004 (4) | −0.010 (4) |
N116 | 0.038 (2) | 0.061 (2) | 0.044 (3) | −0.003 (2) | 0.005 (2) | 0.020 (2) |
C117 | 0.038 (3) | 0.054 (3) | 0.048 (3) | −0.011 (3) | 0.006 (2) | −0.002 (3) |
C118 | 0.091 (5) | 0.067 (4) | 0.052 (4) | 0.025 (4) | 0.007 (3) | 0.000 (3) |
C119 | 0.085 (5) | 0.072 (5) | 0.059 (4) | 0.021 (4) | 0.000 (3) | 0.004 (3) |
C120 | 0.079 (5) | 0.080 (5) | 0.070 (5) | 0.006 (4) | −0.008 (4) | 0.018 (4) |
C121 | 0.078 (5) | 0.063 (4) | 0.085 (5) | 0.016 (4) | −0.012 (4) | −0.008 (4) |
C122 | 0.070 (4) | 0.067 (4) | 0.063 (4) | 0.009 (3) | −0.015 (3) | −0.013 (3) |
P201 | 0.0449 (7) | 0.0553 (9) | 0.0389 (7) | 0.0122 (7) | −0.0074 (5) | −0.0093 (6) |
O202 | 0.048 (2) | 0.088 (3) | 0.0461 (19) | 0.014 (2) | −0.0079 (15) | −0.010 (2) |
N203 | 0.051 (2) | 0.065 (3) | 0.043 (2) | 0.020 (2) | −0.0087 (19) | −0.019 (2) |
C204 | 0.061 (4) | 0.074 (5) | 0.089 (5) | 0.017 (4) | −0.001 (4) | −0.034 (4) |
C205 | 0.031 (2) | 0.048 (3) | 0.028 (2) | 0.002 (2) | 0.0008 (18) | −0.003 (2) |
C206 | 0.047 (3) | 0.087 (5) | 0.049 (3) | 0.010 (3) | 0.010 (3) | 0.021 (3) |
C207 | 0.044 (3) | 0.103 (6) | 0.090 (5) | −0.011 (4) | 0.020 (3) | 0.008 (4) |
C208 | 0.032 (3) | 0.148 (7) | 0.049 (3) | 0.013 (4) | −0.010 (3) | 0.015 (4) |
C209 | 0.045 (4) | 0.199 (10) | 0.068 (5) | 0.002 (5) | 0.000 (3) | 0.065 (6) |
C210 | 0.041 (3) | 0.101 (6) | 0.073 (4) | 0.003 (3) | 0.005 (3) | 0.027 (4) |
N211 | 0.038 (2) | 0.056 (3) | 0.0435 (18) | −0.002 (2) | −0.0106 (16) | −0.007 (2) |
C212 | 0.046 (3) | 0.059 (4) | 0.059 (4) | −0.014 (3) | 0.004 (3) | 0.007 (3) |
C214 | 0.027 (3) | 0.085 (5) | 0.076 (4) | −0.005 (3) | −0.006 (3) | 0.009 (4) |
C213 | 0.064 (4) | 0.071 (4) | 0.054 (4) | −0.020 (3) | −0.005 (3) | 0.008 (3) |
C215 | 0.068 (4) | 0.060 (4) | 0.087 (5) | −0.014 (3) | 0.004 (4) | −0.006 (4) |
N216 | 0.040 (2) | 0.0606 (19) | 0.041 (2) | 0.0109 (18) | 0.0015 (19) | 0.009 (2) |
C217 | 0.040 (3) | 0.066 (4) | 0.056 (3) | 0.000 (3) | −0.002 (2) | −0.001 (3) |
C218 | 0.087 (5) | 0.073 (5) | 0.050 (3) | −0.010 (4) | 0.020 (3) | 0.002 (3) |
C219 | 0.086 (5) | 0.092 (6) | 0.084 (5) | −0.020 (5) | 0.021 (4) | 0.002 (5) |
C220 | 0.097 (6) | 0.100 (7) | 0.077 (5) | −0.027 (5) | 0.023 (4) | 0.021 (5) |
C221 | 0.071 (5) | 0.096 (6) | 0.092 (6) | −0.020 (4) | 0.013 (4) | −0.002 (5) |
C222 | 0.071 (4) | 0.073 (5) | 0.066 (4) | 0.012 (4) | 0.028 (3) | 0.025 (4) |
P301 | 0.0311 (6) | 0.0518 (8) | 0.0314 (6) | −0.0016 (6) | 0.0017 (5) | 0.0080 (6) |
O302 | 0.038 (2) | 0.079 (3) | 0.051 (2) | −0.0159 (19) | −0.0031 (17) | 0.018 (2) |
N303 | 0.047 (2) | 0.058 (3) | 0.031 (2) | −0.003 (2) | −0.0035 (18) | 0.020 (2) |
C304 | 0.047 (3) | 0.077 (4) | 0.039 (3) | −0.008 (3) | 0.001 (2) | 0.017 (3) |
C305 | 0.037 (3) | 0.087 (5) | 0.036 (3) | −0.015 (3) | 0.003 (2) | 0.022 (3) |
C306 | 0.042 (3) | 0.065 (4) | 0.080 (5) | −0.002 (3) | 0.012 (3) | −0.006 (3) |
C307 | 0.033 (3) | 0.090 (6) | 0.112 (6) | −0.011 (3) | 0.002 (3) | 0.024 (5) |
C308 | 0.039 (3) | 0.113 (6) | 0.069 (4) | −0.009 (4) | −0.012 (3) | 0.015 (4) |
C309 | 0.068 (5) | 0.127 (7) | 0.076 (5) | −0.007 (4) | −0.015 (4) | −0.030 (5) |
C310 | 0.040 (3) | 0.100 (6) | 0.073 (4) | 0.005 (3) | −0.006 (3) | −0.020 (4) |
N311 | 0.039 (2) | 0.087 (4) | 0.037 (2) | 0.008 (2) | −0.0046 (19) | −0.010 (2) |
C312 | 0.063 (4) | 0.072 (4) | 0.050 (3) | 0.022 (3) | 0.002 (3) | −0.008 (3) |
C3131 | 0.116 (17) | 0.069 (15) | 0.091 (16) | 0.037 (13) | −0.005 (14) | 0.010 (12) |
C3132 | 0.098 (8) | 0.076 (7) | 0.080 (7) | 0.014 (6) | 0.019 (6) | −0.007 (5) |
C3141 | 0.092 (16) | 0.15 (2) | 0.040 (13) | 0.020 (15) | −0.020 (13) | −0.034 (14) |
C3142 | 0.048 (5) | 0.155 (10) | 0.037 (4) | 0.014 (5) | −0.005 (4) | −0.024 (5) |
C3151 | 0.081 (16) | 0.21 (2) | 0.084 (16) | 0.003 (15) | 0.050 (12) | 0.000 (14) |
C3152 | 0.040 (5) | 0.195 (13) | 0.081 (7) | 0.016 (6) | 0.013 (4) | −0.052 (8) |
N316 | 0.041 (2) | 0.061 (3) | 0.040 (2) | 0.005 (2) | −0.0007 (19) | 0.004 (2) |
C317 | 0.065 (4) | 0.066 (4) | 0.042 (3) | 0.012 (3) | −0.001 (3) | −0.007 (3) |
C3182 | 0.095 (15) | 0.097 (13) | 0.124 (14) | 0.053 (13) | 0.064 (12) | 0.023 (11) |
C3181 | 0.073 (11) | 0.089 (9) | 0.147 (13) | 0.012 (9) | 0.082 (10) | 0.036 (10) |
C3191 | 0.090 (10) | 0.074 (8) | 0.101 (11) | 0.022 (6) | 0.032 (8) | −0.012 (8) |
C3192 | 0.125 (13) | 0.072 (10) | 0.055 (9) | 0.037 (9) | 0.020 (9) | 0.010 (8) |
C320 | 0.089 (5) | 0.083 (6) | 0.092 (6) | 0.011 (4) | 0.030 (4) | −0.012 (4) |
C3211 | 0.140 (13) | 0.075 (10) | 0.104 (12) | 0.012 (10) | 0.063 (11) | 0.009 (8) |
C3212 | 0.099 (13) | 0.109 (14) | 0.098 (13) | 0.044 (12) | 0.031 (11) | 0.027 (11) |
C3221 | 0.066 (8) | 0.087 (9) | 0.088 (9) | 0.012 (7) | 0.045 (7) | −0.020 (8) |
C3222 | 0.083 (11) | 0.107 (12) | 0.086 (11) | 0.044 (10) | 0.039 (9) | 0.028 (10) |
P401 | 0.0288 (6) | 0.0361 (7) | 0.0282 (6) | −0.0017 (5) | 0.0043 (4) | 0.0024 (5) |
O402 | 0.0380 (19) | 0.056 (2) | 0.0365 (18) | 0.0125 (16) | 0.0051 (15) | 0.0104 (16) |
N403 | 0.041 (2) | 0.053 (3) | 0.031 (2) | 0.006 (2) | 0.0057 (17) | 0.0107 (19) |
C404 | 0.044 (3) | 0.070 (4) | 0.045 (3) | 0.005 (3) | 0.010 (2) | 0.020 (3) |
C405 | 0.038 (3) | 0.067 (4) | 0.033 (3) | 0.011 (3) | 0.008 (2) | 0.013 (3) |
C406 | 0.030 (3) | 0.080 (5) | 0.070 (4) | −0.003 (3) | 0.011 (3) | −0.028 (3) |
C407 | 0.053 (4) | 0.157 (8) | 0.066 (4) | 0.021 (5) | 0.014 (3) | −0.027 (5) |
C408 | 0.039 (3) | 0.086 (5) | 0.075 (4) | 0.004 (3) | 0.021 (3) | 0.002 (4) |
C409 | 0.030 (3) | 0.078 (5) | 0.128 (6) | 0.005 (3) | 0.014 (3) | 0.014 (5) |
C410 | 0.039 (3) | 0.049 (4) | 0.087 (5) | 0.001 (3) | 0.010 (3) | −0.018 (3) |
N411 | 0.039 (2) | 0.067 (3) | 0.035 (2) | −0.007 (2) | 0.0099 (18) | −0.007 (2) |
C412 | 0.046 (3) | 0.050 (3) | 0.038 (3) | −0.005 (3) | 0.001 (2) | −0.003 (2) |
C413 | 0.051 (3) | 0.083 (5) | 0.054 (4) | −0.022 (3) | 0.014 (3) | −0.009 (3) |
C414 | 0.057 (4) | 0.092 (5) | 0.070 (4) | −0.023 (4) | 0.023 (3) | −0.043 (4) |
C415 | 0.063 (4) | 0.103 (6) | 0.070 (4) | −0.026 (4) | −0.007 (3) | 0.022 (4) |
N416 | 0.031 (2) | 0.049 (3) | 0.041 (2) | −0.0075 (19) | 0.0072 (17) | −0.004 (2) |
C417 | 0.041 (3) | 0.055 (4) | 0.051 (3) | 0.011 (3) | −0.010 (2) | −0.011 (3) |
C418 | 0.098 (6) | 0.125 (7) | 0.085 (5) | −0.053 (5) | 0.035 (4) | −0.044 (5) |
C419 | 0.132 (7) | 0.118 (7) | 0.067 (5) | −0.038 (6) | −0.009 (5) | −0.019 (5) |
C420 | 0.067 (4) | 0.061 (5) | 0.114 (6) | −0.027 (4) | 0.007 (4) | −0.022 (4) |
C421 | 0.104 (6) | 0.153 (9) | 0.092 (6) | −0.076 (6) | 0.017 (5) | −0.029 (6) |
C422 | 0.080 (5) | 0.104 (6) | 0.061 (4) | −0.042 (4) | −0.001 (3) | −0.004 (4) |
P101—O102 | 1.487 (3) | C305—C310 | 1.489 (9) |
P101—N103 | 1.664 (4) | C306—H3061 | 0.972 |
P101—N111 | 1.623 (4) | C306—H3062 | 0.976 |
P101—N116 | 1.608 (5) | C306—C307 | 1.533 (8) |
P201—O202 | 1.490 (4) | C307—H3071 | 0.963 |
P201—N203 | 1.697 (4) | C307—H3072 | 0.974 |
P201—N211 | 1.595 (4) | C307—C308 | 1.496 (9) |
P201—N216 | 1.617 (5) | C308—H3081 | 0.954 |
P301—O302 | 1.475 (4) | C308—H3082 | 0.957 |
P301—N303 | 1.653 (4) | C308—C309 | 1.527 (9) |
P301—N311 | 1.635 (4) | C309—H3091 | 0.962 |
P301—N316 | 1.621 (4) | C309—H3092 | 0.970 |
P401—O402 | 1.493 (3) | C309—C310 | 1.515 (8) |
P401—N403 | 1.643 (4) | C310—H3101 | 0.969 |
P401—N411 | 1.631 (4) | C310—H3102 | 0.958 |
P401—N416 | 1.639 (4) | N311—H3111 | 0.854 (16) |
N103—C104 | 1.432 (7) | N311—C312 | 1.446 (4) |
N103—C105 | 1.509 (5) | C312—C3132 | 1.505 (6) |
C104—H1041 | 0.954 | C312—C3142 | 1.464 (6) |
C104—H1042 | 0.951 | C312—C3152 | 1.511 (6) |
C104—H1043 | 0.954 | C312—C3131 | 1.506 (7) |
C105—H1051 | 0.965 | C312—C3141 | 1.460 (9) |
C105—C106 | 1.509 (7) | C312—C3151 | 1.533 (9) |
C105—C110 | 1.514 (6) | C3131—H3132 | 0.960 |
C106—H1061 | 0.965 | C3131—H3133 | 0.960 |
C106—H1062 | 0.967 | C3131—H3134 | 0.960 |
C106—C107 | 1.558 (7) | C3132—H3135 | 0.950 |
C107—H1071 | 0.965 | C3132—H3136 | 0.950 |
C107—H1072 | 0.956 | C3132—H3137 | 0.949 |
C107—C108 | 1.486 (9) | C3141—H3142 | 0.950 |
C108—H1081 | 0.968 | C3141—H3143 | 0.950 |
C108—H1082 | 0.961 | C3141—H3144 | 0.950 |
C108—C109 | 1.499 (9) | C3142—H3145 | 0.960 |
C109—H1091 | 0.971 | C3142—H3146 | 0.960 |
C109—H1092 | 0.959 | C3142—H3147 | 0.960 |
C109—C110 | 1.571 (7) | C3151—H3152 | 0.960 |
C110—H1101 | 0.964 | C3151—H3153 | 0.960 |
C110—H1102 | 0.969 | C3151—H3154 | 0.960 |
N111—H1111 | 0.840 (16) | C3152—H3155 | 0.950 |
N111—C112 | 1.453 (7) | C3152—H3156 | 0.950 |
C112—C113 | 1.522 (7) | C3152—H3157 | 0.950 |
C112—C114 | 1.532 (7) | N316—H3161 | 0.851 (16) |
C112—C115 | 1.539 (8) | N316—C317 | 1.462 (6) |
C113—H1131 | 0.953 | C317—C3181 | 1.474 (8) |
C113—H1132 | 0.953 | C317—C3221 | 1.523 (8) |
C113—H1133 | 0.955 | C317—H3171 | 0.950 |
C114—H1141 | 0.963 | C317—C3182 | 1.501 (9) |
C114—H1142 | 0.957 | C317—C3222 | 1.455 (9) |
C114—H1143 | 0.962 | C317—H3172 | 0.950 |
C115—H1151 | 0.961 | C3182—H3184 | 0.950 |
C115—H1152 | 0.962 | C3182—H3185 | 0.950 |
C115—H1153 | 0.959 | C3182—C3192 | 1.491 (9) |
N116—H1161 | 0.835 (16) | C3181—H3182 | 0.950 |
N116—C117 | 1.435 (6) | C3181—H3183 | 0.950 |
C117—H1171 | 0.981 | C3181—C3191 | 1.487 (9) |
C117—C118 | 1.533 (7) | C3191—H3192 | 0.950 |
C117—C122 | 1.482 (8) | C3191—H3193 | 0.950 |
C118—H1811 | 0.967 | C3191—C320 | 1.498 (8) |
C118—H1182 | 0.967 | H3194—C3192 | 0.950 |
C118—C119 | 1.498 (8) | C3192—H3195 | 0.950 |
C119—H1191 | 0.968 | C3192—C320 | 1.489 (9) |
C119—H1192 | 0.966 | C320—H3201 | 0.950 |
C119—C120 | 1.479 (9) | C320—H3202 | 0.950 |
C120—H1201 | 0.967 | C320—C3211 | 1.480 (8) |
C120—H1202 | 0.965 | C320—H3203 | 0.950 |
C120—C121 | 1.554 (8) | C320—H3204 | 0.950 |
C121—H1211 | 0.974 | C320—C3212 | 1.517 (9) |
C121—H1212 | 0.973 | C3211—H3212 | 0.950 |
C121—C122 | 1.498 (8) | C3211—H3213 | 0.950 |
C122—H1221 | 0.971 | C3211—C3221 | 1.504 (9) |
C122—H1223 | 0.973 | C3212—H3214 | 0.950 |
N203—C204 | 1.452 (7) | C3212—H3215 | 0.950 |
N203—C205 | 1.446 (6) | C3212—C3222 | 1.501 (9) |
C204—H2041 | 0.957 | C3221—H3222 | 0.950 |
C204—H2042 | 0.956 | C3221—H3223 | 0.950 |
C204—H2043 | 0.951 | C3222—H3224 | 0.950 |
C205—H2051 | 0.962 | C3222—H3225 | 0.950 |
C205—C206 | 1.524 (6) | N403—C404 | 1.452 (6) |
C205—C210 | 1.554 (7) | N403—C405 | 1.492 (6) |
C206—H2061 | 0.985 | C404—H4041 | 0.948 |
C206—H2062 | 0.965 | C404—H4042 | 0.945 |
C206—C207 | 1.510 (8) | C404—H4043 | 0.939 |
C207—H2071 | 0.978 | C405—H4051 | 0.967 |
C207—H2072 | 0.970 | C405—C406 | 1.506 (8) |
C207—C208 | 1.524 (9) | C405—C410 | 1.502 (7) |
C208—H2081 | 0.966 | C406—H4061 | 0.956 |
C208—H2082 | 0.970 | C406—H4062 | 0.956 |
C208—C209 | 1.561 (8) | C406—C407 | 1.568 (7) |
C209—H2091 | 0.984 | C407—H4071 | 0.961 |
C209—H2092 | 0.970 | C407—H4072 | 0.971 |
C209—C210 | 1.512 (8) | C407—C408 | 1.488 (8) |
C210—H2101 | 0.977 | C408—H4081 | 0.953 |
C210—H2102 | 0.975 | C408—H4082 | 0.961 |
N211—H2111 | 0.846 (16) | C408—C409 | 1.497 (9) |
N211—C212 | 1.496 (6) | C409—H4091 | 0.975 |
C212—C214 | 1.565 (7) | C409—H4092 | 0.967 |
C212—C213 | 1.522 (7) | C409—C410 | 1.537 (7) |
C212—C215 | 1.471 (8) | C410—H4101 | 0.966 |
C214—H2141 | 0.962 | C410—H4102 | 0.969 |
C214—H2142 | 0.955 | N411—H4111 | 0.850 (16) |
C214—H2143 | 0.953 | N411—C412 | 1.453 (6) |
C213—H2131 | 0.943 | C412—C413 | 1.549 (7) |
C213—H2132 | 0.954 | C412—C414 | 1.513 (7) |
C213—H2133 | 0.957 | C412—C415 | 1.512 (8) |
C215—H2151 | 0.947 | C413—H4131 | 0.963 |
C215—H2152 | 0.958 | C413—H4132 | 0.966 |
C215—H2153 | 0.956 | C413—H4133 | 0.969 |
N216—H2161 | 0.843 (16) | C414—H4141 | 0.966 |
N216—C217 | 1.428 (7) | C414—H4142 | 0.953 |
C217—H2171 | 0.987 | C414—H4143 | 0.948 |
C217—C218 | 1.525 (7) | C415—H4151 | 0.972 |
C217—C222 | 1.491 (8) | C415—H4152 | 0.958 |
C218—H2182 | 0.970 | C415—H4153 | 0.964 |
C218—H2181 | 0.975 | N416—H4161 | 0.838 (16) |
C218—C219 | 1.502 (8) | N416—C417 | 1.439 (6) |
C219—H2191 | 0.980 | C417—H4171 | 0.968 |
C219—H2192 | 0.972 | C417—C418 | 1.549 (8) |
C219—C220 | 1.476 (9) | C417—C422 | 1.444 (8) |
C220—H2201 | 0.968 | C418—H4181 | 0.973 |
C220—H2202 | 0.966 | C418—H4182 | 0.972 |
C220—C221 | 1.516 (9) | C418—C419 | 1.542 (9) |
C221—H2211 | 0.983 | C419—H4191 | 0.979 |
C221—H2212 | 0.979 | C419—H4192 | 0.966 |
C221—C222 | 1.554 (8) | C419—C420 | 1.463 (9) |
C222—H2221 | 0.977 | C420—H4201 | 0.966 |
C222—H2222 | 0.982 | C420—H4202 | 0.954 |
N303—C304 | 1.461 (6) | C420—C421 | 1.475 (10) |
N303—C305 | 1.463 (6) | C421—H4211 | 0.964 |
C304—H3041 | 0.943 | C421—H4212 | 0.970 |
C304—H3042 | 0.954 | C421—C422 | 1.527 (9) |
C304—H3043 | 0.957 | C422—H4221 | 0.969 |
C305—H3051 | 0.975 | C422—H4222 | 0.971 |
C305—C306 | 1.540 (7) | ||
O102—P101—N103 | 107.3 (2) | H3051—C305—C310 | 108.1 |
O102—P101—N111 | 112.2 (2) | C306—C305—C310 | 109.5 (5) |
N103—P101—N111 | 114.7 (2) | C305—C306—H3061 | 108.7 |
O102—P101—N116 | 116.5 (2) | C305—C306—H3062 | 111.3 |
N103—P101—N116 | 104.8 (2) | H3061—C306—H3062 | 109.3 |
N111—P101—N116 | 101.4 (2) | C305—C306—C307 | 110.4 (5) |
O202—P201—N203 | 107.8 (2) | H3061—C306—C307 | 107.9 |
O202—P201—N211 | 112.6 (2) | H3062—C306—C307 | 109.2 |
N203—P201—N211 | 113.9 (2) | C306—C307—H3071 | 108.3 |
O202—P201—N216 | 116.8 (2) | C306—C307—H3072 | 109.9 |
N203—P201—N216 | 104.3 (2) | H3071—C307—H3072 | 109.1 |
N211—P201—N216 | 101.3 (2) | C306—C307—C308 | 112.3 (6) |
P101—N103—C104 | 120.8 (4) | H3071—C307—C308 | 108.5 |
P101—N111—C112 | 128.4 (4) | H3072—C307—C308 | 108.6 |
P201—N203—C204 | 118.3 (4) | C307—C308—H3081 | 108.6 |
P201—N216—C217 | 127.1 (4) | C307—C308—H3082 | 109.4 |
P301—N303—C304 | 119.0 (3) | H3081—C308—H3082 | 109.3 |
P301—N311—C312 | 128.6 (2) | C307—C308—C309 | 110.2 (6) |
P401—N403—C404 | 118.9 (3) | H3081—C308—C309 | 109.2 |
P401—N411—C412 | 129.0 (3) | H3082—C308—C309 | 110.2 |
O302—P301—N303 | 107.0 (2) | C308—C309—H3091 | 109.2 |
O302—P301—N311 | 115.5 (2) | C308—C309—H3092 | 109.9 |
N303—P301—N311 | 110.0 (2) | H3091—C309—H3092 | 110.1 |
O302—P301—N316 | 114.9 (2) | C308—C309—C310 | 109.7 (5) |
N303—P301—N316 | 110.0 (2) | H3091—C309—C310 | 108.5 |
N311—P301—N316 | 99.4 (2) | H3092—C309—C310 | 109.4 |
O402—P401—N403 | 107.88 (19) | C309—C310—C305 | 113.2 (6) |
O402—P401—N411 | 113.7 (2) | C309—C310—H3101 | 108.4 |
N403—P401—N411 | 112.6 (2) | C305—C310—H3101 | 110.3 |
O402—P401—N416 | 116.5 (2) | C309—C310—H3102 | 107.2 |
N403—P401—N416 | 106.1 (2) | C305—C310—H3102 | 108.8 |
N411—P401—N416 | 99.7 (2) | H3101—C310—H3102 | 108.9 |
P101—N103—C105 | 118.4 (3) | P301—N311—H3111 | 111.9 (12) |
P101—N116—C117 | 130.0 (4) | H3111—N311—C312 | 111.7 (12) |
P201—N203—C205 | 119.5 (3) | N311—C312—C3132 | 106.78 (9) |
P201—N211—C212 | 128.7 (4) | N311—C312—C3142 | 116.67 (9) |
P301—N303—C305 | 123.6 (3) | C3132—C312—C3142 | 103.05 (9) |
P301—N316—C317 | 124.1 (4) | N311—C312—C3152 | 107.78 (9) |
P401—N403—C405 | 124.2 (3) | C3132—C312—C3152 | 109.93 (9) |
P401—N416—C417 | 125.4 (3) | C3142—C312—C3152 | 112.31 (9) |
C104—N103—C105 | 117.2 (4) | N311—C312—C3131 | 106.81 (9) |
N103—C104—H1041 | 112.6 | N311—C312—C3141 | 116.72 (9) |
N103—C104—H1042 | 109.6 | C3131—C312—C3141 | 103.09 (9) |
H1041—C104—H1042 | 108.8 | N311—C312—C3151 | 107.68 (9) |
N103—C104—H1043 | 108.0 | C3131—C312—C3151 | 109.90 (9) |
H1041—C104—H1043 | 109.5 | C3141—C312—C3151 | 112.32 (9) |
H1042—C104—H1043 | 108.3 | C312—C3131—H3132 | 109.8 |
N103—C105—H1051 | 106.9 | C312—C3131—H3133 | 111.7 |
N103—C105—C106 | 112.9 (4) | H3132—C3131—H3133 | 109.4 |
H1051—C105—C106 | 108.0 | C312—C3131—H3134 | 107.1 |
N103—C105—C110 | 110.1 (4) | H3132—C3131—H3134 | 109.4 |
H1051—C105—C110 | 108.4 | H3133—C3131—H3134 | 109.4 |
C106—C105—C110 | 110.3 (4) | C312—C3132—H3135 | 109.6 |
C105—C106—H1061 | 110.5 | C312—C3132—H3136 | 109.8 |
C105—C106—H1062 | 109.7 | H3135—C3132—H3136 | 109.5 |
H1061—C106—H1062 | 107.3 | C312—C3132—H3137 | 109.0 |
C105—C106—C107 | 109.2 (5) | H3135—C3132—H3137 | 109.5 |
H1061—C106—C107 | 109.7 | H3136—C3132—H3137 | 109.5 |
H1062—C106—C107 | 110.4 | C312—C3141—H3142 | 110.9 |
C106—C107—H1071 | 109.4 | C312—C3141—H3143 | 103.8 |
C106—C107—H1072 | 108.8 | H3142—C3141—H3143 | 109.4 |
H1071—C107—H1072 | 109.8 | C312—C3141—H3144 | 113.5 |
C106—C107—C108 | 110.4 (5) | H3142—C3141—H3144 | 109.5 |
H1071—C107—C108 | 108.4 | H3143—C3141—H3144 | 109.5 |
H1072—C107—C108 | 110.1 | C312—C3142—H3145 | 111.2 |
C107—C108—H1081 | 108.4 | C312—C3142—H3146 | 109.6 |
C107—C108—H1082 | 108.9 | H3145—C3142—H3146 | 109.4 |
H1081—C108—H1082 | 109.5 | C312—C3142—H3147 | 107.7 |
C107—C108—C109 | 110.7 (5) | H3145—C3142—H3147 | 109.4 |
H1081—C108—C109 | 110.9 | H3146—C3142—H3147 | 109.4 |
H1082—C108—C109 | 108.4 | C312—C3151—H3152 | 108.2 |
C108—C109—H1091 | 110.3 | C312—C3151—H3153 | 109.6 |
C108—C109—H1092 | 109.0 | H3152—C3151—H3153 | 109.4 |
H1091—C109—H1092 | 108.8 | C312—C3151—H3154 | 110.9 |
C108—C109—C110 | 110.3 (6) | H3152—C3151—H3154 | 109.4 |
H1091—C109—C110 | 109.5 | H3153—C3151—H3154 | 109.4 |
H1092—C109—C110 | 108.9 | C312—C3152—H3155 | 110.6 |
C105—C110—C109 | 108.6 (4) | C312—C3152—H3156 | 108.2 |
C105—C110—H1101 | 110.2 | H3155—C3152—H3156 | 109.5 |
C109—C110—H1101 | 110.7 | C312—C3152—H3157 | 109.5 |
C105—C110—H1102 | 107.3 | H3155—C3152—H3157 | 109.5 |
C109—C110—H1102 | 109.5 | H3156—C3152—H3157 | 109.5 |
H1101—C110—H1102 | 110.4 | P301—N316—H3161 | 114.7 (12) |
P101—N111—H1111 | 114.6 (10) | H3161—N316—C317 | 115.7 (11) |
H1111—N111—C112 | 115.4 (10) | N316—C317—C3181 | 121.7 (7) |
N111—C112—C113 | 109.1 (4) | N316—C317—C3221 | 109.8 (6) |
N111—C112—C114 | 112.1 (5) | C3181—C317—C3221 | 105.7 (9) |
C113—C112—C114 | 107.8 (5) | N316—C317—H3171 | 104.8 |
N111—C112—C115 | 111.0 (5) | C3181—C317—H3171 | 108.7 |
C113—C112—C115 | 107.9 (5) | C3221—C317—H3171 | 105.1 |
C114—C112—C115 | 108.8 (5) | N316—C317—C3182 | 109.4 (7) |
C112—C113—H1131 | 111.6 | N316—C317—C3222 | 124.7 (6) |
C112—C113—H1132 | 105.7 | C3182—C317—C3222 | 116.1 (11) |
H1131—C113—H1132 | 111.1 | N316—C317—H3172 | 99.0 |
C112—C113—H1133 | 109.2 | C3182—C317—H3172 | 103.8 |
H1131—C113—H1133 | 109.9 | C3222—C317—H3172 | 99.0 |
H1132—C113—H1133 | 109.2 | C317—C3182—H3184 | 108.7 |
C112—C114—H1141 | 108.5 | C317—C3182—H3185 | 106.6 |
C112—C114—H1142 | 110.1 | H3184—C3182—H3185 | 109.5 |
H1141—C114—H1142 | 110.3 | C317—C3182—C3192 | 119.6 (12) |
C112—C114—H1143 | 108.0 | H3184—C3182—C3192 | 106.8 |
H1141—C114—H1143 | 109.7 | H3185—C3182—C3192 | 105.4 |
H1142—C114—H1143 | 110.2 | C317—C3181—H3182 | 110.0 |
C112—C115—H1151 | 110.0 | C317—C3181—H3183 | 106.3 |
C112—C115—H1152 | 109.2 | H3182—C3181—H3183 | 109.5 |
H1151—C115—H1152 | 110.3 | C317—C3181—C3191 | 110.9 (10) |
C112—C115—H1153 | 107.1 | H3182—C3181—C3191 | 112.2 |
H1151—C115—H1153 | 110.1 | H3183—C3181—C3191 | 107.7 |
H1152—C115—H1153 | 110.1 | C3181—C3191—H3192 | 104.4 |
P101—N116—H1161 | 113.9 (11) | C3181—C3191—H3193 | 113.5 |
H1161—N116—C117 | 113.6 (11) | H3192—C3191—H3193 | 109.5 |
N116—C117—H1171 | 107.0 | C3181—C3191—C320 | 110.2 (11) |
N116—C117—C118 | 112.3 (4) | H3192—C3191—C320 | 108.8 |
H1171—C117—C118 | 107.6 | H3193—C3191—C320 | 110.3 |
N116—C117—C122 | 114.2 (5) | C3182—C3192—H3194 | 112.1 |
H1171—C117—C122 | 106.1 | C3182—C3192—H3195 | 108.4 |
C118—C117—C122 | 109.2 (5) | H3194—C3192—H3195 | 109.5 |
C117—C118—H1811 | 106.9 | C3182—C3192—C320 | 109.1 (13) |
C117—C118—H1182 | 110.8 | H3194—C3192—C320 | 110.4 |
H1811—C118—H1182 | 109.3 | H3195—C3192—C320 | 107.2 |
C117—C118—C119 | 112.0 (5) | C3191—C320—H3201 | 108.2 |
H1811—C118—C119 | 109.1 | C3191—C320—H3202 | 110.1 |
H1182—C118—C119 | 108.8 | H3201—C320—H3202 | 109.4 |
C118—C119—H1191 | 108.1 | C3191—C320—C3211 | 111.7 (10) |
C118—C119—H1192 | 109.9 | H3201—C320—C3211 | 109.5 |
H1191—C119—H1192 | 109.0 | H3202—C320—C3211 | 107.9 |
C118—C119—C120 | 113.6 (6) | C3192—C320—H3203 | 109.9 |
H1191—C119—C120 | 107.3 | C3192—C320—H3204 | 108.4 |
H1192—C119—C120 | 108.8 | H3203—C320—H3204 | 109.4 |
C119—C120—H1201 | 111.1 | C3192—C320—C3212 | 106.7 (11) |
C119—C120—H1202 | 107.1 | H3203—C320—C3212 | 108.4 |
H1201—C120—H1202 | 109.6 | H3204—C320—C3212 | 114.0 |
C119—C120—C121 | 111.4 (6) | C320—C3211—H3212 | 109.8 |
H1201—C120—C121 | 109.0 | C320—C3211—H3213 | 107.8 |
H1202—C120—C121 | 108.6 | H3212—C3211—H3213 | 109.5 |
C120—C121—H1211 | 110.0 | C320—C3211—C3221 | 107.5 (9) |
C120—C121—H1212 | 108.7 | H3212—C3211—C3221 | 114.2 |
H1211—C121—H1212 | 109.8 | H3213—C3211—C3221 | 107.9 |
C120—C121—C122 | 111.0 (5) | C320—C3212—H3214 | 106.5 |
H1211—C121—C122 | 107.1 | C320—C3212—H3215 | 113.3 |
H1212—C121—C122 | 110.2 | H3214—C3212—H3215 | 109.5 |
C121—C122—C117 | 115.5 (5) | C320—C3212—C3222 | 115.7 (12) |
C121—C122—H1221 | 107.2 | H3214—C3212—C3222 | 99.6 |
C117—C122—H1221 | 109.2 | H3215—C3212—C3222 | 111.1 |
C121—C122—H1223 | 107.9 | C317—C3221—C3211 | 116.1 (10) |
C117—C122—H1223 | 106.7 | C317—C3221—H3222 | 107.7 |
H1221—C122—H1223 | 110.3 | C3211—C3221—H3222 | 105.9 |
C204—N203—C205 | 117.0 (4) | C317—C3221—H3223 | 109.2 |
N203—C204—H2041 | 109.5 | C3211—C3221—H3223 | 108.3 |
N203—C204—H2042 | 109.7 | H3222—C3221—H3223 | 109.5 |
H2041—C204—H2042 | 110.5 | C3212—C3222—C317 | 108.4 (11) |
N203—C204—H2043 | 108.0 | C3212—C3222—H3224 | 110.9 |
H2041—C204—H2043 | 108.4 | C317—C3222—H3224 | 104.8 |
H2042—C204—H2043 | 110.6 | C3212—C3222—H3225 | 113.8 |
N203—C205—H2051 | 106.5 | C317—C3222—H3225 | 109.0 |
N203—C205—C206 | 111.9 (4) | H3224—C3222—H3225 | 109.5 |
H2051—C205—C206 | 106.7 | P401—N403—C404 | 118.9 (3) |
N203—C205—C210 | 113.8 (4) | C404—N403—C405 | 116.4 (4) |
H2051—C205—C210 | 109.1 | N403—C404—H4041 | 112.0 |
C206—C205—C210 | 108.4 (4) | N403—C404—H4042 | 109.7 |
C205—C206—H2061 | 107.9 | H4041—C404—H4042 | 107.4 |
C205—C206—H2062 | 109.9 | N403—C404—H4043 | 107.9 |
H2061—C206—H2062 | 109.1 | H4041—C404—H4043 | 110.1 |
C205—C206—C207 | 111.5 (4) | H4042—C404—H4043 | 109.6 |
H2061—C206—C207 | 108.9 | N403—C405—H4051 | 106.9 |
H2062—C206—C207 | 109.4 | N403—C405—C406 | 111.9 (4) |
C206—C207—H2071 | 108.9 | H4051—C405—C406 | 108.8 |
C206—C207—H2072 | 109.8 | N403—C405—C410 | 111.7 (4) |
H2071—C207—H2072 | 109.3 | H4051—C405—C410 | 106.2 |
C206—C207—C208 | 111.4 (5) | C406—C405—C410 | 111.1 (4) |
H2071—C207—C208 | 108.4 | C405—C406—H4061 | 109.0 |
H2072—C207—C208 | 109.0 | C405—C406—H4062 | 111.2 |
C207—C208—H2081 | 110.7 | H4061—C406—H4062 | 109.0 |
C207—C208—H2082 | 110.7 | C405—C406—C407 | 110.1 (5) |
H2081—C208—H2082 | 109.3 | H4061—C406—C407 | 108.5 |
C207—C208—C209 | 107.9 (5) | H4062—C406—C407 | 109.0 |
H2081—C208—C209 | 109.8 | C406—C407—H4071 | 108.2 |
H2082—C208—C209 | 108.4 | C406—C407—H4072 | 110.1 |
C208—C209—H2091 | 105.7 | H4071—C407—H4072 | 110.1 |
C208—C209—H2092 | 110.9 | C406—C407—C408 | 110.5 (5) |
H2091—C209—H2092 | 109.8 | H4071—C407—C408 | 107.1 |
C208—C209—C210 | 110.4 (5) | H4072—C407—C408 | 110.8 |
H2091—C209—C210 | 108.4 | C407—C408—H4081 | 108.5 |
H2092—C209—C210 | 111.4 | C407—C408—H4082 | 108.3 |
C205—C210—C209 | 111.8 (6) | H4081—C408—H4082 | 109.0 |
C205—C210—H2101 | 108.1 | C407—C408—C409 | 111.8 (6) |
C209—C210—H2101 | 108.0 | H4081—C408—C409 | 110.1 |
C205—C210—H2102 | 108.9 | H4082—C408—C409 | 109.1 |
C209—C210—H2102 | 109.6 | C408—C409—H4091 | 108.8 |
H2101—C210—H2102 | 110.4 | C408—C409—H4092 | 109.5 |
P201—N211—H2111 | 115.0 (10) | H4091—C409—H4092 | 110.2 |
H2111—N211—C212 | 115.2 (10) | C408—C409—C410 | 111.0 (5) |
N211—C212—C214 | 110.2 (5) | H4091—C409—C410 | 107.3 |
N211—C212—C213 | 108.2 (4) | H4092—C409—C410 | 110.0 |
C214—C212—C213 | 107.5 (5) | C409—C410—C405 | 110.8 (5) |
N211—C212—C215 | 111.7 (5) | C409—C410—H4101 | 109.3 |
C214—C212—C215 | 107.5 (5) | C405—C410—H4101 | 109.1 |
C213—C212—C215 | 111.7 (5) | C409—C410—H4102 | 109.4 |
C212—C214—H2141 | 109.4 | C405—C410—H4102 | 108.1 |
C212—C214—H2142 | 107.3 | H4101—C410—H4102 | 110.1 |
H2141—C214—H2142 | 110.9 | P401—N411—H4111 | 114.5 (10) |
C212—C214—H2143 | 109.3 | H4111—N411—C412 | 115.6 (10) |
H2141—C214—H2143 | 109.2 | N411—C412—C413 | 107.8 (4) |
H2142—C214—H2143 | 110.6 | N411—C412—C414 | 112.9 (4) |
C212—C213—H2131 | 109.1 | C413—C412—C414 | 110.0 (5) |
C212—C213—H2132 | 110.0 | N411—C412—C415 | 109.7 (5) |
H2131—C213—H2132 | 109.6 | C413—C412—C415 | 106.8 (5) |
C212—C213—H2133 | 110.5 | C414—C412—C415 | 109.5 (5) |
H2131—C213—H2133 | 108.4 | C412—C413—H4131 | 109.3 |
H2132—C213—H2133 | 109.2 | C412—C413—H4132 | 109.4 |
C212—C215—H2151 | 108.7 | H4131—C413—H4132 | 109.5 |
C212—C215—H2152 | 109.6 | C412—C413—H4133 | 109.5 |
H2151—C215—H2152 | 110.7 | H4131—C413—H4133 | 109.3 |
C212—C215—H2153 | 109.1 | H4132—C413—H4133 | 109.9 |
H2151—C215—H2153 | 109.9 | C412—C414—H4141 | 109.7 |
H2152—C215—H2153 | 109.0 | C412—C414—H4142 | 107.9 |
P201—N216—H2161 | 104.6 (13) | H4141—C414—H4142 | 108.8 |
H2161—N216—C217 | 105.2 (13) | C412—C414—H4143 | 110.1 |
N216—C217—H2171 | 105.7 | H4141—C414—H4143 | 111.0 |
N216—C217—C218 | 113.2 (5) | H4142—C414—H4143 | 109.3 |
H2171—C217—C218 | 108.3 | C412—C415—H4151 | 110.1 |
N216—C217—C222 | 111.6 (5) | C412—C415—H4152 | 107.3 |
H2171—C217—C222 | 106.9 | H4151—C415—H4152 | 110.2 |
C218—C217—C222 | 110.8 (5) | C412—C415—H4153 | 109.8 |
C217—C218—H2182 | 109.3 | H4151—C415—H4153 | 109.9 |
C217—C218—H2181 | 108.5 | H4152—C415—H4153 | 109.5 |
H2182—C218—H2181 | 110.1 | P401—N416—H4161 | 117.3 (10) |
C217—C218—C219 | 111.4 (6) | H4161—N416—C417 | 116.2 (10) |
H2182—C218—C219 | 108.6 | N416—C417—H4171 | 107.3 |
H2181—C218—C219 | 109.0 | N416—C417—C418 | 109.1 (4) |
C218—C219—H2191 | 107.9 | H4171—C417—C418 | 107.1 |
C218—C219—H2192 | 108.1 | N416—C417—C422 | 114.8 (5) |
H2191—C219—H2192 | 109.7 | H4171—C417—C422 | 108.2 |
C218—C219—C220 | 113.2 (6) | C418—C417—C422 | 110.1 (5) |
H2191—C219—C220 | 109.6 | C417—C418—H4181 | 109.2 |
H2192—C219—C220 | 108.2 | C417—C418—H4182 | 108.5 |
C219—C220—H2201 | 109.1 | H4181—C418—H4182 | 111.0 |
C219—C220—H2202 | 108.5 | C417—C418—C419 | 109.7 (6) |
H2201—C220—H2202 | 109.9 | H4181—C418—C419 | 109.1 |
C219—C220—C221 | 112.3 (7) | H4182—C418—C419 | 109.4 |
H2201—C220—C221 | 107.2 | C418—C419—H4191 | 106.9 |
H2202—C220—C221 | 109.9 | C418—C419—H4192 | 109.1 |
C220—C221—H2211 | 110.1 | H4191—C419—H4192 | 111.1 |
C220—C221—H2212 | 108.7 | C418—C419—C420 | 112.1 (6) |
H2211—C221—H2212 | 109.2 | H4191—C419—C420 | 108.2 |
C220—C221—C222 | 109.6 (6) | H4192—C419—C420 | 109.4 |
H2211—C221—C222 | 109.2 | C419—C420—H4201 | 109.2 |
H2212—C221—C222 | 110.0 | C419—C420—H4202 | 109.1 |
C221—C222—C217 | 113.0 (5) | H4201—C420—H4202 | 109.7 |
C221—C222—H2221 | 107.2 | C419—C420—C421 | 111.0 (7) |
C217—C222—H2221 | 111.4 | H4201—C420—C421 | 108.6 |
C221—C222—H2222 | 108.0 | H4202—C420—C421 | 109.2 |
C217—C222—H2222 | 107.0 | C420—C421—H4211 | 109.0 |
H2221—C222—H2222 | 110.2 | C420—C421—H4212 | 107.6 |
C304—N303—C305 | 117.2 (4) | H4211—C421—H4212 | 110.1 |
N303—C304—H3041 | 109.1 | C420—C421—C422 | 113.9 (6) |
N303—C304—H3042 | 110.6 | H4211—C421—C422 | 109.5 |
H3041—C304—H3042 | 109.7 | H4212—C421—C422 | 106.6 |
N303—C304—H3043 | 108.8 | C421—C422—C417 | 110.7 (6) |
H3041—C304—H3043 | 108.7 | C421—C422—H4221 | 109.8 |
H3042—C304—H3043 | 109.8 | C417—C422—H4221 | 109.1 |
N303—C305—H3051 | 107.1 | C421—C422—H4222 | 109.4 |
N303—C305—C306 | 112.4 (5) | C417—C422—H4222 | 108.6 |
H3051—C305—C306 | 106.5 | H4221—C422—H4222 | 109.2 |
N303—C305—C310 | 112.9 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N111—H1111···O302i | 0.84 | 2.06 | 2.896 (11) | 170 (2) |
N211—H2111···O402ii | 0.85 | 2.07 | 2.873 (11) | 158 (4) |
N216—H2161···O402ii | 0.84 | 2.29 | 3.062 (11) | 152 (2) |
N311—H3111···O202 | 0.85 | 2.08 | 2.914 (11) | 165 (3) |
C3142—H3147···O302 | 0.96 | 2.40 | 3.155 (11) | 135 (1) |
N316—H3161···O202 | 0.85 | 2.28 | 3.086 (11) | 158 (1) |
N411—H4111···O102 | 0.85 | 2.11 | 2.915 (11) | 159 (4) |
N416—H4161···O102 | 0.84 | 2.50 | 3.118 (11) | 132 (4) |
Symmetry codes: (i) −x+1, y+1/2, −z; (ii) −x+1, y−1/2, −z+1. |
C20H34N3OP | F(000) = 2376 |
Mr = 363.47 | Dx = 1.144 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9910 reflections |
a = 10.9207 (4) Å | θ = 1.9–29.1° |
b = 24.0557 (7) Å | µ = 0.14 mm−1 |
c = 24.3993 (8) Å | T = 175 K |
β = 98.980 (3)° | Prism, colourless |
V = 6331.3 (4) Å3 | 0.45 × 0.35 × 0.32 mm |
Z = 12 |
Agilent Xcalibur (Sapphire3, Gemini) diffractometer | 14733 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 10640 reflections with I > 2.0σ(I) |
Graphite monochromator | Rint = 0.047 |
Detector resolution: 16.0143 pixels mm-1 | θmax = 29.1°, θmin = 1.7° |
ω scans | h = −14→13 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | k = −30→32 |
Tmin = 0.915, Tmax = 1.000 | l = −33→31 |
44340 measured reflections |
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.058 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.152 | Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)2]2 Ai are: 0.275E + 04 0.448E + 04 0.294E + 04 0.134E + 04 368. |
S = 0.90 | (Δ/σ)max = 0.001 |
13613 reflections | Δρmax = 0.41 e Å−3 |
694 parameters | Δρmin = −0.40 e Å−3 |
18 restraints |
C20H34N3OP | V = 6331.3 (4) Å3 |
Mr = 363.47 | Z = 12 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.9207 (4) Å | µ = 0.14 mm−1 |
b = 24.0557 (7) Å | T = 175 K |
c = 24.3993 (8) Å | 0.45 × 0.35 × 0.32 mm |
β = 98.980 (3)° |
Agilent Xcalibur (Sapphire3, Gemini) diffractometer | 14733 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | 10640 reflections with I > 2.0σ(I) |
Tmin = 0.915, Tmax = 1.000 | Rint = 0.047 |
44340 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | 18 restraints |
wR(F2) = 0.152 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.90 | Δρmax = 0.41 e Å−3 |
13613 reflections | Δρmin = −0.40 e Å−3 |
694 parameters |
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1 K. Cosier, J. & Glazer, A·M., 1986. J. Appl. Cryst. 105–107. Absorption correction: CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01–02-2013 CrysAlis171. NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
x | y | z | Uiso*/Ueq | ||
P1 | 0.47559 (5) | 0.94135 (2) | 0.20928 (2) | 0.0249 | |
O2 | 0.60692 (15) | 0.93762 (7) | 0.23589 (7) | 0.0361 | |
N3 | 0.44706 (17) | 1.00683 (8) | 0.19333 (9) | 0.0302 | |
C4 | 0.3219 (2) | 1.02441 (10) | 0.16849 (10) | 0.0318 | |
C5 | 0.2511 (3) | 1.05149 (13) | 0.21048 (12) | 0.0447 | |
C6 | 0.1201 (3) | 1.06757 (15) | 0.18380 (14) | 0.0572 | |
C7 | 0.1223 (3) | 1.10541 (16) | 0.13472 (17) | 0.0669 | |
C8 | 0.1920 (3) | 1.07814 (16) | 0.09204 (15) | 0.0624 | |
C9 | 0.3235 (3) | 1.06174 (14) | 0.11803 (13) | 0.0509 | |
H91 | 0.3683 | 1.0953 | 0.1298 | 0.0616* | |
H92 | 0.3648 | 1.0425 | 0.0915 | 0.0610* | |
H82 | 0.1942 | 1.1034 | 0.0616 | 0.0743* | |
H81 | 0.1476 | 1.0451 | 0.0772 | 0.0731* | |
H72 | 0.1651 | 1.1395 | 0.1474 | 0.0814* | |
H71 | 0.0391 | 1.1153 | 0.1178 | 0.0816* | |
H62 | 0.0780 | 1.0873 | 0.2107 | 0.0685* | |
H61 | 0.0739 | 1.0340 | 0.1713 | 0.0687* | |
H52 | 0.2952 | 1.0864 | 0.2232 | 0.0552* | |
H51 | 0.2512 | 1.0259 | 0.2427 | 0.0546* | |
H41 | 0.2766 | 0.9911 | 0.1558 | 0.0364* | |
C10 | 0.5346 (3) | 1.04985 (11) | 0.21573 (14) | 0.0477 | |
H102 | 0.5444 | 1.0762 | 0.1875 | 0.0735* | |
H101 | 0.5040 | 1.0694 | 0.2452 | 0.0725* | |
H103 | 0.6142 | 1.0334 | 0.2294 | 0.0721* | |
N11 | 0.43436 (19) | 0.90457 (8) | 0.15331 (8) | 0.0303 | |
C12 | 0.5056 (2) | 0.90347 (10) | 0.10721 (9) | 0.0302 | |
C13 | 0.5845 (3) | 0.85158 (13) | 0.10809 (12) | 0.0448 | |
C14 | 0.6525 (3) | 0.84820 (15) | 0.05808 (12) | 0.0512 | |
C15 | 0.5636 (3) | 0.85252 (16) | 0.00434 (13) | 0.0587 | |
C16 | 0.4904 (5) | 0.9055 (2) | 0.00350 (13) | 0.0929 | |
C17 | 0.4191 (3) | 0.90816 (19) | 0.05253 (12) | 0.0670 | |
H171 | 0.3783 | 0.9435 | 0.0525 | 0.0791* | |
H172 | 0.3583 | 0.8797 | 0.0513 | 0.0794* | |
H162 | 0.5462 | 0.9367 | 0.0062 | 0.1096* | |
H161 | 0.4324 | 0.9069 | −0.0305 | 0.1099* | |
H152 | 0.6102 | 0.8521 | −0.0265 | 0.0699* | |
H151 | 0.5111 | 0.8210 | 0.0014 | 0.0701* | |
H141 | 0.7136 | 0.8773 | 0.0605 | 0.0627* | |
H142 | 0.6927 | 0.8116 | 0.0580 | 0.0617* | |
H132 | 0.6436 | 0.8506 | 0.1422 | 0.0546* | |
H131 | 0.5310 | 0.8206 | 0.1073 | 0.0546* | |
H121 | 0.5604 | 0.9363 | 0.1118 | 0.0364* | |
H111 | 0.384 (2) | 0.8782 (9) | 0.1547 (8) | 0.0374* | |
N18 | 0.3755 (2) | 0.91658 (9) | 0.24739 (8) | 0.0341 | |
C19 | 0.3678 (2) | 0.92806 (9) | 0.30296 (9) | 0.0298 | |
C20 | 0.2756 (2) | 0.90175 (10) | 0.32726 (10) | 0.0326 | |
C21 | 0.2653 (3) | 0.91139 (11) | 0.38199 (11) | 0.0385 | |
C22 | 0.3427 (3) | 0.94824 (11) | 0.41453 (10) | 0.0396 | |
C23 | 0.4329 (3) | 0.97454 (12) | 0.39018 (11) | 0.0451 | |
C24 | 0.4470 (3) | 0.96481 (11) | 0.33542 (10) | 0.0409 | |
H241 | 0.5111 | 0.9840 | 0.3212 | 0.0486* | |
H231 | 0.4853 | 1.0003 | 0.4109 | 0.0545* | |
C25 | 0.3293 (4) | 0.95894 (16) | 0.47434 (12) | 0.0623 | |
H251 | 0.3869 | 0.9857 | 0.4912 | 0.0933* | |
H253 | 0.2508 | 0.9738 | 0.4758 | 0.0934* | |
H252 | 0.3388 | 0.9268 | 0.4952 | 0.0941* | |
H211 | 0.2044 | 0.8935 | 0.3974 | 0.0463* | |
H201 | 0.2213 | 0.8774 | 0.3056 | 0.0391* | |
H181 | 0.324 (2) | 0.8915 (10) | 0.2320 (8) | 0.0412* | |
P26 | 0.12843 (5) | 0.80954 (2) | 0.19056 (2) | 0.0254 | |
O27 | 0.25851 (15) | 0.82610 (7) | 0.18767 (7) | 0.0343 | |
N28 | 0.11142 (19) | 0.77271 (8) | 0.24504 (8) | 0.0329 | |
C29 | 0.1925 (2) | 0.72674 (10) | 0.26575 (10) | 0.0298 | |
C30 | 0.1156 (2) | 0.67664 (11) | 0.27648 (14) | 0.0464 | |
C31 | 0.1963 (3) | 0.62814 (12) | 0.30068 (16) | 0.0551 | |
C32 | 0.2817 (3) | 0.64564 (15) | 0.35279 (14) | 0.0604 | |
C33 | 0.3615 (3) | 0.69409 (14) | 0.34139 (15) | 0.0630 | |
C34 | 0.2813 (3) | 0.74315 (12) | 0.31767 (13) | 0.0514 | |
H341 | 0.3312 | 0.7744 | 0.3092 | 0.0621* | |
H342 | 0.2331 | 0.7554 | 0.3453 | 0.0617* | |
H332 | 0.4149 | 0.7064 | 0.3747 | 0.0749* | |
H331 | 0.4136 | 0.6810 | 0.3150 | 0.0732* | |
H322 | 0.2322 | 0.6558 | 0.3814 | 0.0715* | |
H321 | 0.3341 | 0.6149 | 0.3665 | 0.0714* | |
H311 | 0.2496 | 0.6163 | 0.2740 | 0.0650* | |
H312 | 0.1458 | 0.5979 | 0.3083 | 0.0665* | |
H302 | 0.0627 | 0.6881 | 0.3030 | 0.0566* | |
H301 | 0.0646 | 0.6668 | 0.2423 | 0.0549* | |
H291 | 0.2417 | 0.7182 | 0.2364 | 0.0324* | |
N35 | 0.0312 (2) | 0.85998 (9) | 0.19863 (8) | 0.0349 | |
C36 | −0.0188 (2) | 0.90067 (9) | 0.16032 (9) | 0.0289 | |
C37 | −0.1209 (2) | 0.93104 (10) | 0.17107 (10) | 0.0317 | |
C38 | −0.1720 (2) | 0.97176 (11) | 0.13485 (11) | 0.0364 | |
C39 | −0.1261 (3) | 0.98252 (11) | 0.08579 (11) | 0.0405 | |
C40 | −0.0260 (3) | 0.95154 (11) | 0.07537 (11) | 0.0412 | |
C41 | 0.0299 (2) | 0.91158 (10) | 0.11192 (10) | 0.0349 | |
H411 | 0.0994 | 0.8916 | 0.1041 | 0.0423* | |
H401 | 0.0059 | 0.9581 | 0.0433 | 0.0486* | |
C42 | −0.1837 (4) | 1.02623 (16) | 0.04606 (14) | 0.0648 | |
H421 | −0.1982 | 1.0129 | 0.0089 | 0.0955* | |
H422 | −0.1288 | 1.0579 | 0.0460 | 0.0965* | |
H423 | −0.2590 | 1.0393 | 0.0552 | 0.0972* | |
H381 | −0.2398 | 0.9915 | 0.1430 | 0.0436* | |
H371 | −0.1536 | 0.9244 | 0.2028 | 0.0385* | |
N43 | 0.07556 (18) | 0.77679 (9) | 0.13289 (8) | 0.0327 | |
C44 | 0.1571 (2) | 0.76066 (11) | 0.09300 (10) | 0.0360 | |
C45 | 0.1043 (3) | 0.77792 (14) | 0.03383 (11) | 0.0521 | |
C46 | 0.1946 (4) | 0.76192 (19) | −0.00602 (13) | 0.0745 | |
C47 | 0.2271 (3) | 0.7005 (2) | −0.00211 (16) | 0.0770 | |
C48 | 0.2785 (3) | 0.6843 (2) | 0.05683 (16) | 0.0775 | |
C49 | 0.1876 (3) | 0.69947 (14) | 0.09567 (13) | 0.0510 | |
H491 | 0.2225 | 0.6901 | 0.1331 | 0.0607* | |
H492 | 0.1111 | 0.6785 | 0.0842 | 0.0609* | |
H482 | 0.3545 | 0.7044 | 0.0677 | 0.0926* | |
H481 | 0.2962 | 0.6442 | 0.0588 | 0.0930* | |
H472 | 0.2861 | 0.6917 | −0.0263 | 0.0897* | |
H471 | 0.1507 | 0.6794 | −0.0141 | 0.0882* | |
H461 | 0.2701 | 0.7836 | 0.0033 | 0.0887* | |
H462 | 0.1550 | 0.7710 | −0.0425 | 0.0882* | |
H452 | 0.0875 | 0.8168 | 0.0324 | 0.0642* | |
H451 | 0.0252 | 0.7588 | 0.0224 | 0.0625* | |
H441 | 0.2327 | 0.7807 | 0.1034 | 0.0406* | |
C50 | −0.0504 (2) | 0.75433 (14) | 0.12585 (13) | 0.0486 | |
H502 | −0.0946 | 0.7615 | 0.0897 | 0.0733* | |
H501 | −0.0942 | 0.7700 | 0.1535 | 0.0718* | |
H503 | −0.0463 | 0.7151 | 0.1303 | 0.0737* | |
P51 | 0.16156 (5) | 0.35488 (2) | 0.17845 (2) | 0.0271 | |
O52 | 0.04339 (16) | 0.33972 (8) | 0.19768 (7) | 0.0359 | |
N53 | 0.15794 (19) | 0.32748 (9) | 0.11670 (8) | 0.0346 | |
C54 | 0.2602 (2) | 0.33834 (11) | 0.08553 (10) | 0.0350 | |
C55 | 0.3472 (3) | 0.28929 (13) | 0.08412 (13) | 0.0490 | |
C56 | 0.4551 (3) | 0.30484 (16) | 0.05468 (15) | 0.0621 | |
C57 | 0.4111 (4) | 0.32655 (16) | −0.00309 (15) | 0.0646 | |
C58 | 0.3223 (3) | 0.37490 (16) | −0.00219 (14) | 0.0595 | |
C59 | 0.2136 (3) | 0.35907 (15) | 0.02723 (12) | 0.0499 | |
H591 | 0.1584 | 0.3903 | 0.0282 | 0.0595* | |
H592 | 0.1676 | 0.3298 | 0.0059 | 0.0601* | |
H582 | 0.3668 | 0.4059 | 0.0176 | 0.0707* | |
H581 | 0.2930 | 0.3878 | −0.0395 | 0.0699* | |
H572 | 0.4809 | 0.3381 | −0.0207 | 0.0773* | |
H571 | 0.3668 | 0.2967 | −0.0256 | 0.0777* | |
H561 | 0.5041 | 0.3336 | 0.0762 | 0.0733* | |
H562 | 0.5073 | 0.2730 | 0.0528 | 0.0731* | |
H551 | 0.3789 | 0.2792 | 0.1219 | 0.0584* | |
H552 | 0.3019 | 0.2584 | 0.0657 | 0.0588* | |
H541 | 0.3081 | 0.3678 | 0.1050 | 0.0418* | |
C60 | 0.0778 (3) | 0.28042 (15) | 0.09958 (13) | 0.0558 | |
H601 | 0.0577 | 0.2786 | 0.0598 | 0.0835* | |
H603 | 0.0048 | 0.2817 | 0.1165 | 0.0826* | |
H602 | 0.1227 | 0.2472 | 0.1131 | 0.0833* | |
N61 | 0.2885 (2) | 0.33601 (9) | 0.21993 (9) | 0.0355 | |
C62 | 0.3181 (2) | 0.28391 (10) | 0.24467 (10) | 0.0320 | |
C63 | 0.2314 (2) | 0.24265 (11) | 0.24819 (13) | 0.0432 | |
C64 | 0.2656 (3) | 0.19387 (11) | 0.27714 (13) | 0.0444 | |
C65 | 0.3853 (3) | 0.18482 (11) | 0.30357 (11) | 0.0407 | |
C66 | 0.4720 (3) | 0.22605 (12) | 0.29817 (12) | 0.0448 | |
C67 | 0.4405 (2) | 0.27428 (11) | 0.26935 (11) | 0.0388 | |
H671 | 0.5020 | 0.3014 | 0.2682 | 0.0479* | |
H661 | 0.5540 | 0.2211 | 0.3149 | 0.0523* | |
C68 | 0.4195 (4) | 0.13368 (14) | 0.33823 (14) | 0.0593 | |
H682 | 0.5044 | 0.1210 | 0.3371 | 0.0912* | |
H681 | 0.4135 | 0.1398 | 0.3769 | 0.0902* | |
H683 | 0.3647 | 0.1037 | 0.3257 | 0.0902* | |
H641 | 0.2046 | 0.1661 | 0.2794 | 0.0531* | |
H631 | 0.1496 | 0.2479 | 0.2305 | 0.0513* | |
H611 | 0.329 (2) | 0.3632 (7) | 0.2353 (10) | 0.0429* | |
N69 | 0.18987 (19) | 0.42091 (9) | 0.17339 (9) | 0.0335 | |
C70 | 0.0980 (2) | 0.46032 (10) | 0.14556 (10) | 0.0344 | |
C71 | 0.0302 (3) | 0.49059 (12) | 0.18642 (11) | 0.0413 | |
C72 | −0.0618 (3) | 0.53364 (13) | 0.15800 (15) | 0.0549 | |
C73 | 0.0003 (3) | 0.57399 (13) | 0.12328 (15) | 0.0571 | |
C74 | 0.0667 (4) | 0.54369 (15) | 0.08228 (15) | 0.0679 | |
C75 | 0.1599 (3) | 0.50162 (14) | 0.11134 (14) | 0.0558 | |
H751 | 0.2232 | 0.5215 | 0.1360 | 0.0679* | |
H752 | 0.1978 | 0.4823 | 0.0839 | 0.0683* | |
H742 | 0.1084 | 0.5701 | 0.0630 | 0.0810* | |
H741 | 0.0031 | 0.5225 | 0.0564 | 0.0803* | |
H732 | 0.0605 | 0.5960 | 0.1480 | 0.0674* | |
H731 | −0.0611 | 0.5985 | 0.1031 | 0.0675* | |
H721 | −0.1010 | 0.5536 | 0.1859 | 0.0668* | |
H722 | −0.1252 | 0.5139 | 0.1338 | 0.0676* | |
H712 | 0.0924 | 0.5093 | 0.2130 | 0.0492* | |
H711 | −0.0121 | 0.4649 | 0.2059 | 0.0497* | |
H701 | 0.0379 | 0.4389 | 0.1200 | 0.0430* | |
H691 | 0.246 (2) | 0.4347 (7) | 0.1979 (9) | 0.0395* | |
H351 | −0.002 (2) | 0.8591 (10) | 0.2275 (9) | 0.0517* | |
H281 | 0.071 (2) | 0.7876 (9) | 0.2672 (8) | 0.0397* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0255 (3) | 0.0256 (3) | 0.0232 (2) | −0.0003 (2) | 0.00278 (19) | 0.0004 (2) |
O2 | 0.0292 (8) | 0.0375 (9) | 0.0387 (9) | 0.0048 (7) | −0.0037 (7) | 0.0011 (7) |
N3 | 0.0245 (9) | 0.0251 (9) | 0.0401 (11) | −0.0027 (7) | 0.0024 (8) | 0.0018 (8) |
C4 | 0.0279 (11) | 0.0287 (11) | 0.0374 (12) | 0.0019 (9) | 0.0005 (9) | 0.0023 (10) |
C5 | 0.0375 (14) | 0.0478 (16) | 0.0475 (15) | 0.0107 (12) | 0.0030 (11) | −0.0070 (13) |
C6 | 0.0406 (16) | 0.068 (2) | 0.0610 (19) | 0.0199 (15) | 0.0008 (14) | −0.0112 (16) |
C7 | 0.0536 (19) | 0.059 (2) | 0.081 (3) | 0.0237 (16) | −0.0127 (17) | −0.0015 (18) |
C8 | 0.059 (2) | 0.062 (2) | 0.060 (2) | 0.0070 (16) | −0.0095 (16) | 0.0199 (17) |
C9 | 0.0478 (16) | 0.0528 (17) | 0.0498 (16) | 0.0029 (13) | 0.0009 (13) | 0.0187 (14) |
C10 | 0.0380 (14) | 0.0314 (13) | 0.071 (2) | −0.0113 (11) | 0.0000 (13) | 0.0012 (13) |
N11 | 0.0332 (10) | 0.0314 (10) | 0.0272 (9) | −0.0063 (8) | 0.0079 (7) | −0.0033 (8) |
C12 | 0.0327 (11) | 0.0337 (12) | 0.0251 (10) | 0.0006 (9) | 0.0068 (8) | −0.0004 (9) |
C13 | 0.0461 (15) | 0.0505 (16) | 0.0397 (14) | 0.0129 (13) | 0.0127 (11) | 0.0030 (12) |
C14 | 0.0486 (16) | 0.0632 (19) | 0.0446 (15) | 0.0120 (14) | 0.0159 (13) | −0.0047 (14) |
C15 | 0.0578 (19) | 0.081 (2) | 0.0404 (15) | 0.0024 (17) | 0.0178 (14) | −0.0204 (16) |
C16 | 0.106 (3) | 0.148 (4) | 0.0258 (14) | 0.069 (3) | 0.0110 (17) | 0.007 (2) |
C17 | 0.061 (2) | 0.109 (3) | 0.0294 (14) | 0.043 (2) | 0.0010 (13) | −0.0028 (16) |
N18 | 0.0428 (12) | 0.0355 (11) | 0.0248 (9) | −0.0145 (9) | 0.0082 (8) | −0.0045 (8) |
C19 | 0.0389 (12) | 0.0274 (11) | 0.0233 (10) | −0.0022 (9) | 0.0049 (9) | 0.0008 (8) |
C20 | 0.0397 (13) | 0.0293 (11) | 0.0291 (11) | −0.0040 (10) | 0.0060 (9) | −0.0019 (9) |
C21 | 0.0457 (14) | 0.0354 (13) | 0.0370 (13) | −0.0022 (11) | 0.0146 (11) | 0.0031 (10) |
C22 | 0.0543 (16) | 0.0398 (14) | 0.0253 (11) | 0.0002 (12) | 0.0079 (10) | −0.0011 (10) |
C23 | 0.0580 (17) | 0.0455 (15) | 0.0309 (13) | −0.0140 (13) | 0.0047 (12) | −0.0083 (11) |
C24 | 0.0510 (15) | 0.0419 (14) | 0.0306 (12) | −0.0174 (12) | 0.0088 (11) | −0.0041 (11) |
C25 | 0.095 (3) | 0.067 (2) | 0.0282 (13) | −0.0119 (19) | 0.0191 (15) | −0.0106 (14) |
P26 | 0.0262 (3) | 0.0247 (3) | 0.0260 (3) | −0.0003 (2) | 0.0062 (2) | −0.0019 (2) |
O27 | 0.0318 (8) | 0.0407 (9) | 0.0314 (8) | −0.0118 (7) | 0.0079 (7) | −0.0099 (7) |
N28 | 0.0359 (11) | 0.0319 (10) | 0.0333 (10) | 0.0097 (8) | 0.0129 (8) | 0.0057 (8) |
C29 | 0.0284 (11) | 0.0286 (11) | 0.0335 (11) | 0.0053 (9) | 0.0079 (9) | 0.0010 (9) |
C30 | 0.0297 (13) | 0.0339 (13) | 0.075 (2) | 0.0031 (10) | 0.0049 (12) | 0.0092 (13) |
C31 | 0.0397 (15) | 0.0308 (13) | 0.095 (3) | 0.0049 (11) | 0.0112 (15) | 0.0165 (15) |
C32 | 0.077 (2) | 0.0584 (19) | 0.0480 (17) | 0.0305 (17) | 0.0174 (16) | 0.0192 (15) |
C33 | 0.069 (2) | 0.0479 (17) | 0.059 (2) | 0.0089 (16) | −0.0285 (17) | −0.0030 (15) |
C34 | 0.0574 (18) | 0.0373 (14) | 0.0521 (17) | 0.0037 (13) | −0.0146 (14) | −0.0039 (13) |
N35 | 0.0456 (12) | 0.0321 (10) | 0.0296 (10) | 0.0096 (9) | 0.0143 (9) | 0.0043 (8) |
C36 | 0.0334 (11) | 0.0246 (10) | 0.0290 (11) | 0.0003 (9) | 0.0056 (9) | −0.0019 (9) |
C37 | 0.0325 (12) | 0.0331 (12) | 0.0301 (11) | 0.0011 (9) | 0.0070 (9) | −0.0014 (9) |
C38 | 0.0329 (12) | 0.0367 (13) | 0.0386 (13) | 0.0076 (10) | 0.0028 (10) | −0.0045 (10) |
C39 | 0.0459 (14) | 0.0386 (14) | 0.0353 (13) | 0.0086 (11) | 0.0006 (11) | 0.0021 (11) |
C40 | 0.0522 (16) | 0.0391 (14) | 0.0340 (12) | 0.0061 (12) | 0.0118 (11) | 0.0091 (11) |
C41 | 0.0415 (13) | 0.0313 (12) | 0.0342 (12) | 0.0078 (10) | 0.0130 (10) | 0.0010 (10) |
C42 | 0.081 (2) | 0.069 (2) | 0.0427 (16) | 0.0335 (19) | 0.0051 (16) | 0.0153 (16) |
N43 | 0.0240 (9) | 0.0413 (11) | 0.0334 (10) | −0.0055 (8) | 0.0060 (8) | −0.0112 (9) |
C44 | 0.0306 (12) | 0.0473 (14) | 0.0312 (11) | −0.0114 (10) | 0.0086 (9) | −0.0155 (11) |
C45 | 0.071 (2) | 0.0527 (17) | 0.0326 (13) | −0.0154 (15) | 0.0062 (13) | −0.0090 (12) |
C46 | 0.081 (3) | 0.111 (3) | 0.0364 (16) | −0.048 (2) | 0.0221 (16) | −0.0247 (19) |
C47 | 0.055 (2) | 0.119 (4) | 0.062 (2) | −0.012 (2) | 0.0260 (17) | −0.050 (2) |
C48 | 0.0496 (19) | 0.112 (3) | 0.071 (2) | 0.016 (2) | 0.0093 (17) | −0.048 (2) |
C49 | 0.0458 (16) | 0.0568 (18) | 0.0501 (16) | 0.0104 (13) | 0.0062 (13) | −0.0160 (14) |
C50 | 0.0268 (12) | 0.070 (2) | 0.0496 (16) | −0.0099 (12) | 0.0061 (11) | −0.0192 (14) |
P51 | 0.0258 (3) | 0.0308 (3) | 0.0250 (3) | −0.0028 (2) | 0.0045 (2) | −0.0021 (2) |
O52 | 0.0321 (9) | 0.0428 (10) | 0.0351 (9) | −0.0051 (7) | 0.0124 (7) | −0.0024 (7) |
N53 | 0.0316 (10) | 0.0434 (12) | 0.0298 (10) | −0.0102 (9) | 0.0075 (8) | −0.0105 (9) |
C54 | 0.0321 (12) | 0.0434 (14) | 0.0307 (11) | −0.0013 (10) | 0.0090 (9) | −0.0050 (10) |
C55 | 0.0518 (17) | 0.0466 (16) | 0.0521 (17) | 0.0101 (13) | 0.0197 (13) | 0.0063 (13) |
C56 | 0.0555 (19) | 0.068 (2) | 0.070 (2) | 0.0229 (16) | 0.0328 (17) | 0.0102 (18) |
C57 | 0.072 (2) | 0.074 (2) | 0.0576 (19) | 0.0147 (19) | 0.0401 (18) | 0.0065 (17) |
C58 | 0.070 (2) | 0.070 (2) | 0.0455 (16) | 0.0147 (17) | 0.0288 (15) | 0.0146 (15) |
C59 | 0.0509 (16) | 0.0641 (19) | 0.0367 (14) | 0.0121 (14) | 0.0133 (12) | 0.0017 (13) |
C60 | 0.0543 (18) | 0.071 (2) | 0.0428 (15) | −0.0298 (16) | 0.0099 (13) | −0.0221 (15) |
N61 | 0.0361 (11) | 0.0299 (10) | 0.0368 (11) | −0.0077 (8) | −0.0063 (8) | −0.0008 (9) |
C62 | 0.0327 (12) | 0.0332 (12) | 0.0295 (11) | −0.0008 (9) | 0.0026 (9) | −0.0035 (9) |
C63 | 0.0314 (13) | 0.0373 (13) | 0.0588 (17) | −0.0007 (10) | 0.0008 (11) | −0.0011 (12) |
C64 | 0.0408 (14) | 0.0321 (13) | 0.0603 (17) | −0.0022 (11) | 0.0082 (12) | −0.0012 (12) |
C65 | 0.0515 (16) | 0.0340 (13) | 0.0370 (13) | 0.0064 (11) | 0.0082 (11) | −0.0043 (10) |
C66 | 0.0392 (14) | 0.0503 (16) | 0.0413 (14) | 0.0095 (12) | −0.0057 (11) | −0.0042 (12) |
C67 | 0.0322 (12) | 0.0436 (14) | 0.0389 (13) | −0.0026 (10) | 0.0005 (10) | −0.0027 (11) |
C68 | 0.081 (2) | 0.0458 (17) | 0.0469 (17) | 0.0110 (16) | −0.0018 (16) | 0.0057 (14) |
N69 | 0.0316 (10) | 0.0329 (10) | 0.0349 (10) | −0.0022 (8) | 0.0020 (8) | −0.0012 (8) |
C70 | 0.0403 (13) | 0.0309 (12) | 0.0309 (11) | −0.0005 (10) | 0.0020 (10) | 0.0012 (10) |
C71 | 0.0442 (14) | 0.0408 (14) | 0.0412 (14) | 0.0026 (11) | 0.0136 (11) | 0.0038 (11) |
C72 | 0.0528 (18) | 0.0441 (16) | 0.069 (2) | 0.0124 (14) | 0.0147 (15) | 0.0052 (15) |
C73 | 0.070 (2) | 0.0373 (15) | 0.063 (2) | 0.0110 (14) | 0.0086 (16) | 0.0087 (14) |
C74 | 0.106 (3) | 0.0485 (18) | 0.0524 (19) | 0.0108 (19) | 0.0227 (19) | 0.0170 (15) |
C75 | 0.074 (2) | 0.0477 (17) | 0.0532 (18) | 0.0092 (15) | 0.0324 (16) | 0.0118 (14) |
P1—O2 | 1.4818 (17) | C37—C38 | 1.378 (3) |
P1—N3 | 1.641 (2) | C37—H371 | 0.916 |
P1—N11 | 1.630 (2) | C38—C39 | 1.392 (4) |
P1—N18 | 1.653 (2) | C38—H381 | 0.927 |
P26—O27 | 1.4876 (17) | C39—C40 | 1.379 (4) |
P26—N28 | 1.632 (2) | C39—C42 | 1.500 (4) |
P26—N35 | 1.644 (2) | C40—C41 | 1.387 (4) |
P26—N43 | 1.637 (2) | C40—H401 | 0.919 |
P51—O52 | 1.4857 (17) | C41—H411 | 0.943 |
P51—N53 | 1.639 (2) | C42—H421 | 0.951 |
P51—N61 | 1.647 (2) | C42—H422 | 0.969 |
P51—N69 | 1.627 (2) | C42—H423 | 0.940 |
N3—C4 | 1.468 (3) | N43—C44 | 1.470 (3) |
N3—C10 | 1.456 (3) | N43—C50 | 1.463 (3) |
C4—C5 | 1.523 (4) | C44—C45 | 1.526 (4) |
C4—C9 | 1.526 (4) | C44—C49 | 1.508 (4) |
C4—H41 | 0.967 | C44—H441 | 0.955 |
C5—C6 | 1.527 (4) | C45—C46 | 1.538 (5) |
C5—H52 | 0.993 | C45—H452 | 0.952 |
C5—H51 | 0.998 | C45—H451 | 0.980 |
C6—C7 | 1.507 (5) | C46—C47 | 1.519 (6) |
C6—H62 | 0.980 | C46—H461 | 0.972 |
C6—H61 | 0.976 | C46—H462 | 0.951 |
C7—C8 | 1.530 (5) | C47—C48 | 1.511 (6) |
C7—H72 | 0.970 | C47—H472 | 0.963 |
C7—H71 | 0.967 | C47—H471 | 0.981 |
C8—C9 | 1.529 (4) | C48—C49 | 1.520 (4) |
C8—H82 | 0.963 | C48—H482 | 0.961 |
C8—H81 | 0.970 | C48—H481 | 0.985 |
C9—H91 | 0.963 | C49—H491 | 0.961 |
C9—H92 | 0.962 | C49—H492 | 0.979 |
C10—H102 | 0.954 | C50—H502 | 0.953 |
C10—H101 | 0.962 | C50—H501 | 0.962 |
C10—H103 | 0.966 | C50—H503 | 0.951 |
N11—C12 | 1.464 (3) | N53—C54 | 1.469 (3) |
N11—H111 | 0.842 (17) | N53—C60 | 1.452 (3) |
C12—C13 | 1.515 (4) | C54—C55 | 1.519 (4) |
C12—C17 | 1.514 (4) | C54—C59 | 1.518 (4) |
C12—H121 | 0.988 | C54—H541 | 0.962 |
C13—C14 | 1.526 (4) | C55—C56 | 1.519 (4) |
C13—H132 | 0.971 | C55—H551 | 0.964 |
C13—H131 | 0.946 | C55—H552 | 0.965 |
C14—C15 | 1.508 (4) | C56—C57 | 1.510 (5) |
C14—H141 | 0.963 | C56—H561 | 0.976 |
C14—H142 | 0.985 | C56—H562 | 0.961 |
C15—C16 | 1.504 (5) | C57—C58 | 1.517 (5) |
C15—H152 | 0.973 | C57—H572 | 0.973 |
C15—H151 | 0.947 | C57—H571 | 0.984 |
C16—C17 | 1.527 (5) | C58—C59 | 1.528 (4) |
C16—H162 | 0.961 | C58—H582 | 0.974 |
C16—H161 | 0.963 | C58—H581 | 0.968 |
C17—H171 | 0.959 | C59—H591 | 0.965 |
C17—H172 | 0.952 | C59—H592 | 0.969 |
N18—C19 | 1.399 (3) | C60—H601 | 0.961 |
N18—H181 | 0.865 (17) | C60—H603 | 0.954 |
C19—C20 | 1.398 (3) | C60—H602 | 0.967 |
C19—C24 | 1.394 (3) | N61—C62 | 1.407 (3) |
C20—C21 | 1.377 (3) | N61—H611 | 0.845 (17) |
C20—H201 | 0.936 | C62—C63 | 1.383 (4) |
C21—C22 | 1.386 (4) | C62—C67 | 1.397 (3) |
C21—H211 | 0.920 | C63—C64 | 1.390 (4) |
C22—C23 | 1.381 (4) | C63—H631 | 0.939 |
C22—C25 | 1.511 (3) | C64—C65 | 1.382 (4) |
C23—C24 | 1.388 (4) | C64—H641 | 0.952 |
C23—H231 | 0.936 | C65—C66 | 1.392 (4) |
C24—H241 | 0.948 | C65—C68 | 1.507 (4) |
C25—H251 | 0.948 | C66—C67 | 1.372 (4) |
C25—H253 | 0.934 | C66—H661 | 0.932 |
C25—H252 | 0.923 | C67—H671 | 0.940 |
N28—C29 | 1.457 (3) | C68—H682 | 0.980 |
N28—H281 | 0.831 (17) | C68—H681 | 0.968 |
C29—C30 | 1.515 (3) | C68—H683 | 0.957 |
C29—C34 | 1.523 (4) | N69—C70 | 1.468 (3) |
C29—H291 | 0.982 | N69—H691 | 0.855 (17) |
C30—C31 | 1.524 (4) | C70—C71 | 1.518 (4) |
C30—H302 | 0.972 | C70—C75 | 1.522 (4) |
C30—H301 | 0.958 | C70—H701 | 0.979 |
C31—C32 | 1.514 (5) | C71—C72 | 1.531 (4) |
C31—H311 | 0.982 | C71—H712 | 0.974 |
C31—H312 | 0.948 | C71—H711 | 0.942 |
C32—C33 | 1.507 (5) | C72—C73 | 1.516 (5) |
C32—H322 | 0.977 | C72—H721 | 0.985 |
C32—H321 | 0.963 | C72—H722 | 0.962 |
C33—C34 | 1.528 (4) | C73—C74 | 1.512 (5) |
C33—H332 | 0.971 | C73—H732 | 0.977 |
C33—H331 | 0.976 | C73—H731 | 0.968 |
C34—H341 | 0.970 | C74—C75 | 1.529 (5) |
C34—H342 | 0.964 | C74—H742 | 0.947 |
N35—C36 | 1.404 (3) | C74—H741 | 1.001 |
N35—H351 | 0.841 (17) | C75—H751 | 0.968 |
C36—C37 | 1.392 (3) | C75—H752 | 0.962 |
C36—C41 | 1.394 (3) | ||
O2—P1—N3 | 107.28 (10) | C37—C36—C41 | 119.0 (2) |
O2—P1—N11 | 117.13 (11) | C36—C37—C38 | 120.5 (2) |
N3—P1—N11 | 107.76 (11) | C36—C37—H371 | 119.8 |
O2—P1—N18 | 114.30 (11) | C38—C37—H371 | 119.7 |
N3—P1—N18 | 111.20 (11) | C37—C38—C39 | 121.3 (2) |
N11—P1—N18 | 98.92 (10) | C37—C38—H381 | 119.0 |
O27—P26—N28 | 114.51 (11) | C39—C38—H381 | 119.7 |
O27—P26—N35 | 116.58 (11) | C38—C39—C40 | 117.4 (2) |
N28—P26—N35 | 98.36 (10) | C38—C39—C42 | 121.0 (3) |
P1—N3—C4 | 120.31 (15) | C40—C39—C42 | 121.6 (3) |
P1—N11—C12 | 122.88 (16) | C39—C40—C41 | 122.6 (2) |
P26—N28—C29 | 123.66 (16) | C39—C40—H401 | 118.8 |
P26—N43—C44 | 121.82 (15) | C41—C40—H401 | 118.7 |
P51—N53—C60 | 120.33 (18) | C36—C41—C40 | 119.2 (2) |
P51—N61—C62 | 128.63 (17) | C36—C41—H411 | 120.1 |
O27—P26—N43 | 107.42 (10) | C40—C41—H411 | 120.7 |
N28—P26—N43 | 111.66 (11) | C39—C42—H421 | 111.8 |
N35—P26—N43 | 108.07 (11) | C39—C42—H422 | 110.8 |
O52—P51—N53 | 107.09 (10) | H421—C42—H422 | 105.9 |
O52—P51—N61 | 115.30 (11) | C39—C42—H423 | 112.0 |
N53—P51—N61 | 110.55 (11) | H421—C42—H423 | 108.5 |
P1—N3—C10 | 120.27 (17) | H422—C42—H423 | 107.5 |
P1—N18—C19 | 128.23 (17) | C44—N43—C50 | 118.7 (2) |
P26—N35—C36 | 128.78 (17) | N43—C44—C45 | 112.1 (2) |
P26—N43—C50 | 118.53 (17) | N43—C44—C49 | 112.4 (2) |
P51—N53—C54 | 119.54 (16) | C45—C44—C49 | 110.8 (2) |
P51—N69—C70 | 122.79 (17) | N43—C44—H441 | 106.2 |
C4—N3—C10 | 117.7 (2) | C45—C44—H441 | 107.2 |
N3—C4—C5 | 112.5 (2) | C49—C44—H441 | 107.7 |
N3—C4—C9 | 112.1 (2) | C44—C45—C46 | 110.2 (3) |
C5—C4—C9 | 111.2 (2) | C44—C45—H452 | 110.2 |
N3—C4—H41 | 106.9 | C46—C45—H452 | 111.1 |
C5—C4—H41 | 106.4 | C44—C45—H451 | 109.1 |
C9—C4—H41 | 107.4 | C46—C45—H451 | 109.1 |
C4—C5—C6 | 111.2 (2) | H452—C45—H451 | 107.0 |
C4—C5—H52 | 107.4 | C45—C46—C47 | 111.7 (3) |
C6—C5—H52 | 107.2 | C45—C46—H461 | 108.8 |
C4—C5—H51 | 109.2 | C47—C46—H461 | 109.0 |
C6—C5—H51 | 112.2 | C45—C46—H462 | 106.9 |
H52—C5—H51 | 109.6 | C47—C46—H462 | 110.5 |
C5—C6—C7 | 111.2 (3) | H461—C46—H462 | 109.9 |
C5—C6—H62 | 110.1 | C46—C47—C48 | 111.0 (3) |
C7—C6—H62 | 107.9 | C46—C47—H472 | 110.3 |
C5—C6—H61 | 109.2 | C48—C47—H472 | 110.0 |
C7—C6—H61 | 108.8 | C46—C47—H471 | 107.7 |
H62—C6—H61 | 109.6 | C48—C47—H471 | 108.9 |
C6—C7—C8 | 110.7 (3) | H472—C47—H471 | 108.8 |
C6—C7—H72 | 109.0 | C47—C48—C49 | 110.5 (3) |
C8—C7—H72 | 108.2 | C47—C48—H482 | 108.1 |
C6—C7—H71 | 110.9 | C49—C48—H482 | 109.1 |
C8—C7—H71 | 110.4 | C47—C48—H481 | 109.9 |
H72—C7—H71 | 107.5 | C49—C48—H481 | 110.3 |
C7—C8—C9 | 111.3 (3) | H482—C48—H481 | 108.9 |
C7—C8—H82 | 109.3 | C48—C49—C44 | 111.6 (3) |
C9—C8—H82 | 110.3 | C48—C49—H491 | 109.6 |
C7—C8—H81 | 109.5 | C44—C49—H491 | 108.8 |
C9—C8—H81 | 109.0 | C48—C49—H492 | 108.1 |
H82—C8—H81 | 107.4 | C44—C49—H492 | 108.6 |
C8—C9—C4 | 111.0 (3) | H491—C49—H492 | 110.1 |
C8—C9—H91 | 108.0 | N43—C50—H502 | 111.8 |
C4—C9—H91 | 108.7 | N43—C50—H501 | 109.6 |
C8—C9—H92 | 110.7 | H502—C50—H501 | 110.0 |
C4—C9—H92 | 108.9 | N43—C50—H503 | 109.1 |
H91—C9—H92 | 109.5 | H502—C50—H503 | 107.2 |
N3—C10—H102 | 109.9 | H501—C50—H503 | 109.1 |
N3—C10—H101 | 110.1 | O52—P51—N69 | 116.65 (11) |
H102—C10—H101 | 107.8 | N53—P51—N69 | 107.49 (11) |
N3—C10—H103 | 110.0 | N61—P51—N69 | 99.44 (11) |
H102—C10—H103 | 108.9 | C54—N53—C60 | 117.5 (2) |
H101—C10—H103 | 110.0 | N53—C54—C55 | 113.7 (2) |
P1—N11—H111 | 118.2 (12) | N53—C54—C59 | 111.9 (2) |
C12—N11—H111 | 116.3 (12) | C55—C54—C59 | 110.7 (2) |
N11—C12—C13 | 111.9 (2) | N53—C54—H541 | 105.9 |
N11—C12—C17 | 110.1 (2) | C55—C54—H541 | 106.9 |
C13—C12—C17 | 110.4 (2) | C59—C54—H541 | 107.3 |
N11—C12—H121 | 106.5 | C54—C55—C56 | 110.7 (2) |
C13—C12—H121 | 108.9 | C54—C55—H551 | 107.8 |
C17—C12—H121 | 108.9 | C56—C55—H551 | 109.0 |
C12—C13—C14 | 112.3 (2) | C54—C55—H552 | 109.4 |
C12—C13—H132 | 109.4 | C56—C55—H552 | 110.4 |
C14—C13—H132 | 110.1 | H551—C55—H552 | 109.5 |
C12—C13—H131 | 107.5 | C55—C56—C57 | 111.7 (3) |
C14—C13—H131 | 108.6 | C55—C56—H561 | 108.7 |
H132—C13—H131 | 108.9 | C57—C56—H561 | 108.9 |
C13—C14—C15 | 111.4 (2) | C55—C56—H562 | 109.6 |
C13—C14—H141 | 109.3 | C57—C56—H562 | 109.7 |
C15—C14—H141 | 110.5 | H561—C56—H562 | 108.1 |
C13—C14—H142 | 108.8 | C56—C57—C58 | 111.3 (3) |
C15—C14—H142 | 106.6 | C56—C57—H572 | 110.8 |
H141—C14—H142 | 110.3 | C58—C57—H572 | 109.5 |
C14—C15—C16 | 109.8 (3) | C56—C57—H571 | 109.0 |
C14—C15—H152 | 109.2 | C58—C57—H571 | 107.9 |
C16—C15—H152 | 109.8 | H572—C57—H571 | 108.2 |
C14—C15—H151 | 108.2 | C57—C58—C59 | 111.2 (3) |
C16—C15—H151 | 111.3 | C57—C58—H582 | 108.8 |
H152—C15—H151 | 108.5 | C59—C58—H582 | 108.8 |
C15—C16—C17 | 111.1 (3) | C57—C58—H581 | 110.5 |
C15—C16—H162 | 109.2 | C59—C58—H581 | 110.8 |
C17—C16—H162 | 108.0 | H582—C58—H581 | 106.6 |
C15—C16—H161 | 108.5 | C58—C59—C54 | 110.5 (3) |
C17—C16—H161 | 109.1 | C58—C59—H591 | 110.6 |
H162—C16—H161 | 111.0 | C54—C59—H591 | 110.5 |
C16—C17—C12 | 111.3 (3) | C58—C59—H592 | 107.8 |
C16—C17—H171 | 109.2 | C54—C59—H592 | 109.5 |
C12—C17—H171 | 107.0 | H591—C59—H592 | 107.8 |
C16—C17—H172 | 112.6 | N53—C60—H601 | 111.0 |
C12—C17—H172 | 108.1 | N53—C60—H603 | 110.9 |
H171—C17—H172 | 108.4 | H601—C60—H603 | 111.3 |
P1—N18—H181 | 116.5 (12) | N53—C60—H602 | 107.1 |
C19—N18—H181 | 115.1 (12) | H601—C60—H602 | 109.2 |
N18—C19—C20 | 118.5 (2) | H603—C60—H602 | 107.0 |
N18—C19—C24 | 123.4 (2) | P51—N61—H611 | 113.3 (12) |
C20—C19—C24 | 118.1 (2) | C62—N61—H611 | 115.3 (12) |
C19—C20—C21 | 120.5 (2) | N61—C62—C63 | 123.5 (2) |
C19—C20—H201 | 118.7 | N61—C62—C67 | 118.2 (2) |
C21—C20—H201 | 120.8 | C63—C62—C67 | 118.2 (2) |
C20—C21—C22 | 121.9 (2) | C62—C63—C64 | 120.4 (2) |
C20—C21—H211 | 119.4 | C62—C63—H631 | 119.1 |
C22—C21—H211 | 118.7 | C64—C63—H631 | 120.5 |
C21—C22—C23 | 117.3 (2) | C63—C64—C65 | 122.0 (3) |
C21—C22—C25 | 121.3 (3) | C63—C64—H641 | 119.2 |
C23—C22—C25 | 121.4 (3) | C65—C64—H641 | 118.8 |
C22—C23—C24 | 122.0 (2) | C64—C65—C66 | 116.9 (3) |
C22—C23—H231 | 119.1 | C64—C65—C68 | 121.7 (3) |
C24—C23—H231 | 118.8 | C66—C65—C68 | 121.4 (3) |
C19—C24—C23 | 120.1 (2) | C65—C66—C67 | 122.1 (3) |
C19—C24—H241 | 121.9 | C65—C66—H661 | 119.3 |
C23—C24—H241 | 118.0 | C67—C66—H661 | 118.6 |
C22—C25—H251 | 112.1 | C62—C67—C66 | 120.5 (3) |
C22—C25—H253 | 109.3 | C62—C67—H671 | 120.8 |
H251—C25—H253 | 105.9 | C66—C67—H671 | 118.6 |
C22—C25—H252 | 111.8 | C65—C68—H682 | 113.0 |
H251—C25—H252 | 108.7 | C65—C68—H681 | 111.9 |
H253—C25—H252 | 108.9 | H682—C68—H681 | 106.5 |
P26—N28—H281 | 115.8 (12) | C65—C68—H683 | 110.3 |
C29—N28—H281 | 117.3 (12) | H682—C68—H683 | 107.7 |
N28—C29—C30 | 109.90 (19) | H681—C68—H683 | 107.1 |
N28—C29—C34 | 111.4 (2) | P51—N69—H691 | 116.7 (12) |
C30—C29—C34 | 111.2 (2) | C70—N69—H691 | 116.0 (12) |
N28—C29—H291 | 106.1 | N69—C70—C71 | 112.0 (2) |
C30—C29—H291 | 110.0 | N69—C70—C75 | 110.2 (2) |
C34—C29—H291 | 108.1 | C71—C70—C75 | 110.6 (2) |
C29—C30—C31 | 111.9 (2) | N69—C70—H701 | 107.2 |
C29—C30—H302 | 107.0 | C71—C70—H701 | 108.9 |
C31—C30—H302 | 109.0 | C75—C70—H701 | 107.8 |
C29—C30—H301 | 108.0 | C70—C71—C72 | 112.3 (2) |
C31—C30—H301 | 111.8 | C70—C71—H712 | 107.4 |
H302—C30—H301 | 109.0 | C72—C71—H712 | 109.2 |
C30—C31—C32 | 110.8 (3) | C70—C71—H711 | 110.1 |
C30—C31—H311 | 109.3 | C72—C71—H711 | 109.5 |
C32—C31—H311 | 106.7 | H712—C71—H711 | 108.2 |
C30—C31—H312 | 110.2 | C71—C72—C73 | 111.6 (3) |
C32—C31—H312 | 110.4 | C71—C72—H721 | 110.0 |
H311—C31—H312 | 109.4 | C73—C72—H721 | 110.8 |
C31—C32—C33 | 111.0 (3) | C71—C72—H722 | 107.6 |
C31—C32—H322 | 109.4 | C73—C72—H722 | 108.4 |
C33—C32—H322 | 109.8 | H721—C72—H722 | 108.4 |
C31—C32—H321 | 109.5 | C72—C73—C74 | 111.3 (3) |
C33—C32—H321 | 109.2 | C72—C73—H732 | 108.6 |
H322—C32—H321 | 108.0 | C74—C73—H732 | 108.9 |
C32—C33—C34 | 110.7 (3) | C72—C73—H731 | 109.9 |
C32—C33—H332 | 111.7 | C74—C73—H731 | 108.9 |
C34—C33—H332 | 108.4 | H732—C73—H731 | 109.2 |
C32—C33—H331 | 106.6 | C73—C74—C75 | 111.5 (3) |
C34—C33—H331 | 110.9 | C73—C74—H742 | 108.9 |
H332—C33—H331 | 108.5 | C75—C74—H742 | 109.7 |
C33—C34—C29 | 111.6 (2) | C73—C74—H741 | 107.7 |
C33—C34—H341 | 111.9 | C75—C74—H741 | 107.6 |
C29—C34—H341 | 109.2 | H742—C74—H741 | 111.6 |
C33—C34—H342 | 108.3 | C74—C75—C70 | 111.5 (3) |
C29—C34—H342 | 108.3 | C74—C75—H751 | 108.7 |
H341—C34—H342 | 107.4 | C70—C75—H751 | 108.4 |
P26—N35—H351 | 116.9 (12) | C74—C75—H752 | 109.0 |
C36—N35—H351 | 113.7 (12) | C70—C75—H752 | 110.1 |
N35—C36—C37 | 118.7 (2) | H751—C75—H752 | 109.2 |
N35—C36—C41 | 122.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H111···O27 | 0.84 | 2.11 | 2.908 (4) | 158 (2) |
N18—H181···O27 | 0.87 | 1.98 | 2.813 (4) | 161 (2) |
C63—H631···O52 | 0.94 | 2.56 | 3.225 (4) | 128 (1) |
N61—H611···O2i | 0.85 | 2.01 | 2.838 (4) | 167 (2) |
N69—H691···O2i | 0.86 | 2.09 | 2.907 (4) | 159 (2) |
N35—H351···O52ii | 0.84 | 2.00 | 2.819 (4) | 163 (2) |
N28—H281···O52ii | 0.83 | 2.05 | 2.854 (4) | 163 (2) |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2. |
C19H38N3OP2 | Dx = 1.182 Mg m−3 |
Mr = 355.51 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pna21 | Cell parameters from 8077 reflections |
a = 21.9179 (10) Å | θ = 2.0–28.1° |
b = 8.9546 (4) Å | µ = 0.15 mm−1 |
c = 20.3544 (14) Å | T = 175 K |
V = 3994.9 (3) Å3 | Block, colourless |
Z = 8 | 0.35 × 0.35 × 0.18 mm |
F(000) = 1568 |
Oxford Diffraction Gemini diffractometer | 6779 reflections with I > 2.0σ(I) |
Graphite monochromator | Rint = 0.050 |
ω scans | θmax = 29.0°, θmin = 1.9° |
Absorption correction: ψ scan (CrysAlis PRO; Agilent, 2011) | h = −29→27 |
Tmin = 0.95, Tmax = 0.97 | k = −11→12 |
33932 measured reflections | l = −25→26 |
9291 independent reflections |
Refinement on F2 | Hydrogen site location: difference Fourier map |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.124 | Method = Modified Sheldrick
w = 1/[σ2(F2) + ( 0.2P)2 + 0.0P]
, where P = (max(Fo2,0) + 2Fc2)/3 |
wR(F2) = 0.326 | (Δ/σ)max = 0.004 |
S = 1.22 | Δρmax = 2.27 e Å−3 |
8783 reflections | Δρmin = −0.55 e Å−3 |
437 parameters | Absolute structure: Flack (1983), 4252 Friedel-pairs |
444 restraints | Absolute structure parameter: 0.3 (2) |
Primary atom site location: other |
C19H38N3OP2 | V = 3994.9 (3) Å3 |
Mr = 355.51 | Z = 8 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 21.9179 (10) Å | µ = 0.15 mm−1 |
b = 8.9546 (4) Å | T = 175 K |
c = 20.3544 (14) Å | 0.35 × 0.35 × 0.18 mm |
Oxford Diffraction Gemini diffractometer | 9291 independent reflections |
Absorption correction: ψ scan (CrysAlis PRO; Agilent, 2011) | 6779 reflections with I > 2.0σ(I) |
Tmin = 0.95, Tmax = 0.97 | Rint = 0.050 |
33932 measured reflections |
R[F2 > 2σ(F2)] = 0.124 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.326 | Δρmax = 2.27 e Å−3 |
S = 1.22 | Δρmin = −0.55 e Å−3 |
8783 reflections | Absolute structure: Flack (1983), 4252 Friedel-pairs |
437 parameters | Absolute structure parameter: 0.3 (2) |
444 restraints |
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1 K. Cosier, J. & Glazer, A·M., 1986. J. Appl. Cryst. 105–107. |
x | y | z | Uiso*/Ueq | ||
P1 | 0.32604 (6) | 0.11891 (13) | 1.01846 (11) | 0.0371 | |
O2 | 0.37209 (14) | 0.0066 (4) | 0.9992 (2) | 0.0402 | |
N3 | 0.3401 (3) | 0.2366 (5) | 1.0762 (3) | 0.0477 | |
C4 | 0.3511 (3) | 0.1924 (7) | 1.1455 (3) | 0.0661 | |
C9 | 0.3245 (5) | 0.2991 (12) | 1.1951 (3) | 0.1046 | |
C5 | 0.4157 (3) | 0.1623 (12) | 1.1640 (4) | 0.1055 | |
C6 | 0.4213 (5) | 0.1103 (9) | 1.2337 (4) | 0.1451 | |
C7 | 0.3973 (4) | 0.2247 (11) | 1.2799 (4) | 0.1341 | |
C8 | 0.3322 (4) | 0.2576 (12) | 1.2659 (4) | 0.1244 | |
N10 | 0.3046 (2) | 0.2389 (5) | 0.9593 (3) | 0.0437 | |
C11 | 0.2861 (2) | 0.1887 (7) | 0.8966 (3) | 0.0566 | |
C12 | 0.2263 (3) | 0.2569 (12) | 0.8780 (4) | 0.1028 | |
C13 | 0.1949 (4) | 0.220 (2) | 0.8159 (5) | 0.1761 | |
C14 | 0.2364 (6) | 0.240 (2) | 0.7595 (4) | 0.1982 | |
C15 | 0.2980 (5) | 0.1793 (18) | 0.7746 (4) | 0.1514 | |
C16 | 0.3263 (4) | 0.2228 (14) | 0.8390 (3) | 0.0999 | |
H101 | 0.3058 | 0.3432 | 0.9679 | 0.0506* | |
N17 | 0.26418 (19) | 0.0240 (4) | 1.0414 (3) | 0.0453 | |
C18 | 0.2597 (2) | −0.1394 (5) | 1.0346 (3) | 0.0434 | |
C19 | 0.2147 (3) | −0.1828 (6) | 0.9814 (3) | 0.0578 | |
C20 | 0.2134 (3) | −0.3503 (7) | 0.9759 (4) | 0.0665 | |
C21 | 0.1959 (3) | −0.4276 (7) | 1.0378 (3) | 0.0693 | |
C22 | 0.2421 (3) | −0.3856 (6) | 1.0895 (4) | 0.0646 | |
C23 | 0.2440 (3) | −0.2188 (6) | 1.0971 (3) | 0.0568 | |
C24 | 0.2110 (3) | 0.1093 (7) | 1.0618 (5) | 0.0684 | |
P25 | 0.42115 (6) | 0.61800 (13) | 0.97976 (12) | 0.0383 | |
O26 | 0.37220 (14) | 0.5047 (4) | 0.9974 (2) | 0.0396 | |
N27 | 0.4382 (2) | 0.7374 (5) | 1.0366 (3) | 0.0456 | |
C28 | 0.4678 (2) | 0.6901 (6) | 1.0979 (3) | 0.0540 | |
C29 | 0.4245 (3) | 0.7038 (14) | 1.1546 (3) | 0.0970 | |
C30 | 0.4579 (4) | 0.6768 (16) | 1.2178 (4) | 0.1216 | |
C31 | 0.5206 (3) | 0.7435 (11) | 1.2202 (3) | 0.0945 | |
C32 | 0.5622 (2) | 0.7183 (17) | 1.1628 (3) | 0.1463 | |
C33 | 0.5306 (3) | 0.7564 (15) | 1.0997 (3) | 0.1389 | |
H271 | 0.421 (2) | 0.824 (3) | 1.0357 (15) | 0.0467* | |
N34 | 0.4020 (2) | 0.7366 (5) | 0.9194 (3) | 0.0470 | |
C35 | 0.3950 (3) | 0.6946 (7) | 0.8532 (2) | 0.0741 | |
C36 | 0.3317 (3) | 0.6708 (14) | 0.8285 (3) | 0.1328 | |
C37 | 0.3322 (4) | 0.6359 (12) | 0.7563 (3) | 0.1444 | |
C38 | 0.3649 (5) | 0.7543 (15) | 0.7190 (4) | 0.1842 | |
C39 | 0.4292 (4) | 0.7680 (17) | 0.7418 (4) | 0.1795 | |
C40 | 0.4317 (5) | 0.8045 (13) | 0.8136 (4) | 0.1507 | |
N41 | 0.48286 (19) | 0.5289 (4) | 0.9574 (3) | 0.0464 | |
C42 | 0.4901 (2) | 0.3653 (5) | 0.9632 (2) | 0.0409 | |
C43 | 0.5064 (4) | 0.2978 (7) | 0.8970 (3) | 0.0671 | |
C44 | 0.5104 (3) | 0.1292 (7) | 0.9047 (4) | 0.0689 | |
C45 | 0.5544 (3) | 0.0803 (7) | 0.9577 (4) | 0.0756 | |
C46 | 0.5396 (4) | 0.1504 (7) | 1.0229 (4) | 0.0823 | |
C47 | 0.5358 (4) | 0.3204 (7) | 1.0159 (4) | 0.0768 | |
C48 | 0.5371 (3) | 0.6096 (6) | 0.9358 (5) | 0.0712 | |
H421 | 0.4513 | 0.3276 | 0.9759 | 0.0514* | |
H431 | 0.5444 | 0.3354 | 0.8818 | 0.0861* | |
H432 | 0.4755 | 0.3206 | 0.8659 | 0.0861* | |
H442 | 0.5237 | 0.0879 | 0.8642 | 0.1041* | |
H31 | 0.3388 | 0.3406 | 1.0669 | 0.0483* | |
H41 | 0.3291 | 0.1022 | 1.1522 | 0.0825* | |
H91 | 0.3481 | 0.3879 | 1.1918 | 0.1649* | |
H92 | 0.2836 | 0.3197 | 1.1826 | 0.1649* | |
H51 | 0.4380 | 0.2527 | 1.1600 | 0.1168* | |
H52 | 0.4334 | 0.0882 | 1.1366 | 0.1168* | |
H61 | 0.4622 | 0.0892 | 1.2461 | 0.1692* | |
H62 | 0.3974 | 0.0223 | 1.2377 | 0.1692* | |
H71 | 0.3995 | 0.1926 | 1.3244 | 0.1757* | |
H72 | 0.4196 | 0.3150 | 1.2749 | 0.1757* | |
H81 | 0.3137 | 0.3284 | 1.2943 | 0.1815* | |
H82 | 0.3109 | 0.1655 | 1.2686 | 0.1815* | |
H111 | 0.2820 | 0.0832 | 0.8983 | 0.0631* | |
H121 | 0.2006 | 0.2305 | 0.9138 | 0.1402* | |
H122 | 0.2309 | 0.3624 | 0.8766 | 0.1402* | |
H131 | 0.1836 | 0.1174 | 0.8190 | 0.2131* | |
H132 | 0.1592 | 0.2791 | 0.8111 | 0.2131* | |
H141 | 0.2359 | 0.3419 | 0.7472 | 0.2450* | |
H142 | 0.2212 | 0.1806 | 0.7243 | 0.2450* | |
H161 | 0.3625 | 0.1653 | 0.8427 | 0.1297* | |
H162 | 0.3363 | 0.3260 | 0.8395 | 0.1297* | |
H181 | 0.2987 | −0.1748 | 1.0216 | 0.0502* | |
H191 | 0.1752 | −0.1462 | 0.9919 | 0.0747* | |
H192 | 0.2276 | −0.1418 | 0.9407 | 0.0747* | |
H201 | 0.2526 | −0.3843 | 0.9625 | 0.0743* | |
H202 | 0.1840 | −0.3776 | 0.9439 | 0.0743* | |
H211 | 0.1970 | −0.5329 | 1.0322 | 0.0827* | |
H212 | 0.1561 | −0.3981 | 1.0509 | 0.0827* | |
H221 | 0.2307 | −0.4294 | 1.1302 | 0.0747* | |
H222 | 0.2814 | −0.4202 | 1.0772 | 0.0747* | |
H231 | 0.2739 | −0.1939 | 1.1290 | 0.0690* | |
H232 | 0.2051 | −0.1848 | 1.1114 | 0.0690* | |
H281 | 0.4778 | 0.5875 | 1.0931 | 0.0661* | |
H291 | 0.4087 | 0.8026 | 1.1555 | 0.1239* | |
H292 | 0.3918 | 0.6347 | 1.1501 | 0.1239* | |
H301 | 0.4359 | 0.7220 | 1.2528 | 0.1593* | |
H302 | 0.4606 | 0.5722 | 1.2252 | 0.1593* | |
H351 | 0.4122 | 0.5977 | 0.8491 | 0.0892* | |
H361 | 0.3104 | 0.7617 | 0.8357 | 0.1591* | |
H362 | 0.3123 | 0.5926 | 0.8521 | 0.1591* | |
H371 | 0.3530 | 0.5443 | 0.7491 | 0.1925* | |
H372 | 0.2910 | 0.6265 | 0.7423 | 0.1925* | |
H381 | 0.3470 | 0.8477 | 0.7298 | 0.2521* | |
H382 | 0.3594 | 0.7351 | 0.6735 | 0.2521* | |
H391 | 0.4475 | 0.8451 | 0.7166 | 0.2047* | |
H392 | 0.4471 | 0.6749 | 0.7306 | 0.2047* | |
H401 | 0.4734 | 0.7858 | 0.8234 | 0.1840* | |
H402 | 0.4225 | 0.9062 | 0.8225 | 0.1840* | |
H441 | 0.4714 | 0.0898 | 0.9152 | 0.0872* | |
H451 | 0.5943 | 0.1108 | 0.9454 | 0.0900* | |
H452 | 0.5536 | −0.0250 | 0.9631 | 0.0900* | |
H461 | 0.5686 | 0.1248 | 1.0557 | 0.0986* | |
H462 | 0.5004 | 0.1153 | 1.0356 | 0.0986* | |
H471 | 0.5236 | 0.3621 | 1.0568 | 0.0812* | |
H472 | 0.5751 | 0.3567 | 1.0045 | 0.0812* | |
H331 | 0.5265 | 0.8664 | 1.0971 | 0.2047* | |
H332 | 0.5538 | 0.7258 | 1.0637 | 0.2047* | |
H311 | 0.5422 | 0.7010 | 1.2545 | 0.0982* | |
H312 | 0.5172 | 0.8469 | 1.2234 | 0.0982* | |
H241 | 0.2200 | 0.2130 | 1.0636 | 0.0866* | |
H242 | 0.1991 | 0.0753 | 1.1041 | 0.0866* | |
H243 | 0.1788 | 0.0927 | 1.0315 | 0.0866* | |
H481 | 0.5275 | 0.7129 | 0.9330 | 0.0934* | |
H482 | 0.5687 | 0.5953 | 0.9671 | 0.0934* | |
H483 | 0.5503 | 0.5748 | 0.8941 | 0.0934* | |
H151 | 0.2952 | 0.0740 | 0.7693 | 0.2334* | |
H152 | 0.3267 | 0.2183 | 0.7441 | 0.2334* | |
H321 | 0.5970 | 0.7812 | 1.1666 | 0.1559* | |
H322 | 0.5750 | 0.6172 | 1.1600 | 0.1559* | |
H341 | 0.4010 | 0.8406 | 0.9286 | 0.0646* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0345 (6) | 0.0299 (6) | 0.0468 (7) | −0.0022 (4) | −0.0023 (5) | 0.0018 (6) |
O2 | 0.0279 (14) | 0.0331 (14) | 0.060 (2) | −0.0005 (10) | 0.0015 (12) | 0.0028 (13) |
N3 | 0.058 (3) | 0.035 (2) | 0.050 (2) | −0.0096 (19) | 0.001 (2) | −0.0041 (15) |
C4 | 0.093 (4) | 0.048 (4) | 0.057 (2) | −0.011 (3) | −0.013 (3) | 0.003 (2) |
C9 | 0.124 (7) | 0.138 (8) | 0.052 (3) | 0.017 (6) | −0.001 (4) | −0.019 (4) |
C5 | 0.102 (5) | 0.105 (6) | 0.110 (5) | 0.018 (5) | −0.019 (5) | 0.020 (6) |
C6 | 0.195 (11) | 0.140 (10) | 0.100 (6) | 0.044 (8) | −0.055 (7) | 0.001 (5) |
C7 | 0.207 (9) | 0.086 (6) | 0.109 (7) | −0.009 (7) | −0.074 (7) | −0.016 (5) |
C8 | 0.198 (9) | 0.113 (7) | 0.063 (3) | 0.013 (7) | −0.024 (6) | −0.009 (5) |
N10 | 0.050 (3) | 0.027 (2) | 0.055 (2) | −0.0045 (16) | −0.015 (2) | 0.0017 (14) |
C11 | 0.071 (3) | 0.041 (3) | 0.057 (2) | 0.000 (2) | −0.021 (2) | 0.001 (2) |
C12 | 0.080 (4) | 0.117 (7) | 0.111 (6) | 0.010 (4) | −0.059 (4) | 0.001 (5) |
C13 | 0.165 (9) | 0.233 (15) | 0.131 (8) | 0.010 (11) | −0.096 (6) | −0.021 (10) |
C14 | 0.210 (12) | 0.265 (18) | 0.119 (7) | 0.007 (12) | −0.084 (7) | −0.024 (12) |
C15 | 0.203 (10) | 0.199 (13) | 0.052 (4) | −0.002 (10) | −0.037 (5) | 0.008 (7) |
C16 | 0.114 (6) | 0.134 (8) | 0.051 (3) | −0.004 (6) | −0.011 (3) | 0.011 (5) |
N17 | 0.0353 (18) | 0.0318 (16) | 0.069 (3) | 0.0010 (13) | 0.0088 (18) | 0.0012 (18) |
C18 | 0.024 (2) | 0.0353 (17) | 0.070 (3) | −0.0023 (16) | 0.0037 (19) | −0.001 (2) |
C19 | 0.053 (3) | 0.053 (2) | 0.067 (3) | −0.003 (2) | −0.012 (3) | 0.002 (3) |
C20 | 0.062 (4) | 0.057 (3) | 0.080 (4) | −0.020 (3) | 0.001 (4) | −0.013 (3) |
C21 | 0.062 (4) | 0.041 (3) | 0.106 (5) | −0.011 (3) | 0.016 (3) | 0.000 (3) |
C22 | 0.077 (4) | 0.039 (2) | 0.077 (4) | 0.005 (3) | 0.015 (3) | 0.007 (3) |
C23 | 0.059 (3) | 0.043 (2) | 0.068 (3) | 0.006 (3) | 0.001 (3) | 0.007 (3) |
C24 | 0.044 (3) | 0.049 (3) | 0.112 (6) | 0.009 (2) | 0.021 (3) | −0.009 (4) |
P25 | 0.0322 (6) | 0.0320 (6) | 0.0507 (8) | 0.0012 (4) | −0.0006 (5) | 0.0005 (6) |
O26 | 0.0278 (13) | 0.0327 (14) | 0.058 (2) | 0.0025 (10) | 0.0014 (12) | 0.0002 (13) |
N27 | 0.047 (3) | 0.040 (2) | 0.049 (2) | −0.0020 (17) | −0.008 (2) | 0.0013 (15) |
C28 | 0.075 (3) | 0.036 (3) | 0.051 (2) | 0.007 (2) | −0.014 (2) | −0.001 (2) |
C29 | 0.099 (5) | 0.137 (8) | 0.055 (3) | −0.032 (6) | 0.002 (3) | −0.001 (5) |
C30 | 0.103 (5) | 0.214 (11) | 0.047 (3) | −0.063 (7) | 0.005 (3) | 0.015 (6) |
C31 | 0.070 (4) | 0.118 (7) | 0.095 (5) | −0.006 (4) | 0.008 (3) | 0.016 (5) |
C32 | 0.068 (5) | 0.296 (16) | 0.075 (5) | −0.020 (8) | −0.004 (3) | 0.007 (7) |
C33 | 0.062 (4) | 0.251 (14) | 0.104 (5) | −0.025 (6) | −0.021 (4) | 0.019 (8) |
N34 | 0.056 (3) | 0.032 (2) | 0.053 (2) | 0.0052 (18) | −0.010 (2) | −0.0013 (15) |
C35 | 0.109 (5) | 0.055 (4) | 0.058 (3) | 0.028 (4) | −0.023 (3) | −0.010 (3) |
C36 | 0.127 (6) | 0.213 (12) | 0.059 (4) | −0.044 (8) | −0.029 (4) | 0.013 (6) |
C37 | 0.114 (8) | 0.259 (16) | 0.060 (5) | −0.011 (8) | −0.028 (5) | 0.002 (6) |
C38 | 0.149 (9) | 0.335 (17) | 0.069 (6) | −0.052 (12) | 0.020 (6) | −0.002 (8) |
C39 | 0.137 (8) | 0.309 (18) | 0.092 (5) | −0.028 (11) | 0.028 (7) | 0.007 (9) |
C40 | 0.116 (8) | 0.254 (14) | 0.081 (5) | −0.031 (8) | 0.007 (6) | 0.041 (8) |
N41 | 0.0356 (17) | 0.0338 (17) | 0.070 (3) | 0.0031 (14) | 0.0084 (18) | 0.0029 (18) |
C42 | 0.039 (2) | 0.0359 (18) | 0.047 (3) | 0.0021 (17) | 0.0032 (18) | 0.0017 (18) |
C43 | 0.080 (4) | 0.064 (3) | 0.058 (3) | 0.019 (3) | 0.013 (3) | −0.005 (3) |
C44 | 0.056 (4) | 0.059 (3) | 0.092 (4) | 0.010 (3) | 0.015 (3) | −0.024 (3) |
C45 | 0.036 (3) | 0.049 (3) | 0.142 (6) | 0.006 (2) | 0.007 (3) | 0.003 (3) |
C46 | 0.077 (5) | 0.055 (3) | 0.115 (5) | 0.017 (3) | −0.037 (5) | 0.008 (4) |
C47 | 0.078 (4) | 0.056 (3) | 0.097 (5) | 0.029 (3) | −0.033 (4) | −0.002 (3) |
C48 | 0.044 (3) | 0.042 (3) | 0.127 (7) | 0.001 (2) | 0.024 (4) | 0.011 (4) |
P1—O2 | 1.478 (4) | C23—H232 | 0.950 |
P1—N3 | 1.608 (5) | C24—H241 | 0.950 |
P1—N10 | 1.680 (5) | C24—H242 | 0.950 |
P1—N17 | 1.667 (4) | C24—H243 | 0.950 |
P25—O26 | 1.520 (4) | N27—C28 | 1.468 (7) |
P25—N27 | 1.619 (5) | N27—H271 | 0.859 (19) |
P25—N34 | 1.677 (5) | C28—C29 | 1.5000 (10) |
P25—N41 | 1.635 (4) | C28—C33 | 1.5002 (10) |
N3—C4 | 1.485 (9) | C28—H281 | 0.950 |
N3—H31 | 0.950 | C29—C30 | 1.5000 (10) |
C4—C9 | 1.507 (5) | C29—H291 | 0.950 |
C4—C5 | 1.490 (5) | C29—H292 | 0.950 |
C4—H41 | 0.950 | C30—C31 | 1.4999 (10) |
C9—C8 | 1.500 (5) | C30—H301 | 0.950 |
C9—H91 | 0.950 | C30—H302 | 0.950 |
C9—H92 | 0.950 | C31—C32 | 1.4994 (10) |
C5—C6 | 1.498 (5) | C31—H311 | 0.924 |
C5—H51 | 0.950 | C31—H312 | 0.931 |
C5—H52 | 0.950 | C32—C33 | 1.4992 (10) |
C6—C7 | 1.488 (5) | C32—H321 | 0.950 |
C6—H61 | 0.950 | C32—H322 | 0.950 |
C6—H62 | 0.950 | C33—H331 | 0.990 |
C7—C8 | 1.484 (5) | C33—H332 | 0.933 |
C7—H71 | 0.950 | N34—C35 | 1.407 (8) |
C7—H72 | 0.950 | N34—H341 | 0.950 |
C8—H81 | 0.950 | C35—C36 | 1.491 (5) |
C8—H82 | 0.950 | C35—C40 | 1.506 (5) |
N10—C11 | 1.413 (8) | C35—H351 | 0.950 |
N10—H101 | 0.950 | C36—C37 | 1.502 (5) |
C11—C12 | 1.497 (4) | C36—H361 | 0.950 |
C11—C16 | 1.498 (5) | C36—H362 | 0.950 |
C11—H111 | 0.950 | C37—C38 | 1.489 (5) |
C12—C13 | 1.477 (5) | C37—H371 | 0.950 |
C12—H121 | 0.950 | C37—H372 | 0.950 |
C12—H122 | 0.950 | C38—C39 | 1.489 (5) |
C13—C14 | 1.477 (5) | C38—H381 | 0.950 |
C13—H131 | 0.950 | C38—H382 | 0.950 |
C13—H132 | 0.950 | C39—C40 | 1.498 (5) |
C14—C15 | 1.485 (5) | C39—H391 | 0.950 |
C14—H141 | 0.950 | C39—H392 | 0.950 |
C14—H142 | 0.950 | C40—H401 | 0.950 |
C15—C16 | 1.502 (5) | C40—H402 | 0.950 |
C15—H151 | 0.950 | N41—C42 | 1.478 (6) |
C15—H152 | 0.950 | N41—C48 | 1.459 (7) |
C16—H161 | 0.950 | C42—C43 | 1.520 (6) |
C16—H162 | 0.950 | C42—C47 | 1.522 (7) |
N17—C18 | 1.474 (6) | C42—H421 | 0.950 |
N17—C24 | 1.453 (7) | C43—C44 | 1.521 (7) |
C18—C19 | 1.514 (6) | C43—H431 | 0.950 |
C18—C23 | 1.497 (7) | C43—H432 | 0.950 |
C18—H181 | 0.950 | C44—C45 | 1.512 (8) |
C19—C20 | 1.504 (6) | C44—H442 | 0.950 |
C19—H191 | 0.950 | C44—H441 | 0.950 |
C19—H192 | 0.950 | C45—C46 | 1.504 (8) |
C20—C21 | 1.487 (7) | C45—H451 | 0.950 |
C20—H201 | 0.950 | C45—H452 | 0.950 |
C20—H202 | 0.950 | C46—C47 | 1.531 (7) |
C21—C22 | 1.509 (7) | C46—H461 | 0.950 |
C21—H211 | 0.950 | C46—H462 | 0.950 |
C21—H212 | 0.950 | C47—H471 | 0.950 |
C22—C23 | 1.502 (6) | C47—H472 | 0.950 |
C22—H221 | 0.950 | C48—H481 | 0.950 |
C22—H222 | 0.950 | C48—H482 | 0.950 |
C23—H231 | 0.950 | C48—H483 | 0.950 |
O2—P1—N3 | 120.6 (3) | C18—C23—H231 | 108.2 |
O2—P1—N10 | 115.9 (3) | C22—C23—H232 | 109.0 |
N3—P1—N10 | 99.1 (2) | C18—C23—H232 | 108.4 |
O2—P1—N17 | 106.44 (19) | H231—C23—H232 | 109.5 |
N3—P1—N17 | 106.5 (3) | N17—C24—H241 | 111.0 |
N10—P1—N17 | 107.4 (2) | N17—C24—H242 | 108.1 |
P1—N3—C4 | 123.4 (4) | H241—C24—H242 | 109.5 |
P1—N17—C24 | 117.7 (4) | N17—C24—H243 | 109.3 |
P25—N27—C28 | 121.2 (4) | H241—C24—H243 | 109.5 |
P25—N41—C48 | 121.0 (3) | H242—C24—H243 | 109.5 |
O26—P25—N27 | 115.7 (3) | P25—N27—H271 | 118.8 (15) |
O26—P25—N34 | 114.8 (2) | C28—N27—H271 | 117.9 (15) |
N27—P25—N34 | 99.4 (2) | N27—C28—C29 | 110.5 (5) |
O26—P25—N41 | 108.9 (2) | N27—C28—C33 | 108.2 (4) |
N27—P25—N41 | 109.3 (2) | C29—C28—C33 | 122.0 (6) |
N34—P25—N41 | 108.2 (3) | N27—C28—H281 | 107.1 |
P1—N10—C11 | 121.6 (4) | C29—C28—H281 | 107.7 |
P1—N17—C18 | 122.3 (3) | C33—C28—H281 | 100.0 |
P25—N34—C35 | 124.0 (4) | C28—C29—C30 | 109.8 (6) |
P25—N41—C42 | 123.4 (4) | C28—C29—H291 | 108.8 |
P1—N3—H31 | 119.4 | C30—C29—H291 | 108.2 |
C4—N3—H31 | 117.1 | C28—C29—H292 | 110.4 |
N3—C4—C9 | 113.8 (5) | C30—C29—H292 | 110.2 |
N3—C4—C5 | 116.3 (6) | H291—C29—H292 | 109.5 |
C9—C4—C5 | 108.3 (7) | C29—C30—C31 | 114.3 (7) |
N3—C4—H41 | 106.3 | C29—C30—H301 | 109.1 |
C9—C4—H41 | 104.3 | C31—C30—H301 | 105.6 |
C5—C4—H41 | 107.0 | C29—C30—H302 | 109.0 |
C4—C9—C8 | 116.3 (7) | C31—C30—H302 | 109.3 |
C4—C9—H91 | 105.9 | H301—C30—H302 | 109.5 |
C8—C9—H91 | 102.2 | C30—C31—C32 | 118.2 (7) |
C4—C9—H92 | 108.1 | C30—C31—H311 | 109.3 |
C8—C9—H92 | 114.3 | C32—C31—H311 | 102.4 |
H91—C9—H92 | 109.5 | C30—C31—H312 | 109.0 |
C4—C5—C6 | 111.9 (7) | C32—C31—H312 | 104.6 |
C4—C5—H51 | 108.3 | H311—C31—H312 | 113.4 |
C6—C5—H51 | 107.7 | C31—C32—C33 | 110.66 (19) |
C4—C5—H52 | 111.5 | C31—C32—H321 | 109.6 |
C6—C5—H52 | 107.8 | C33—C32—H321 | 107.7 |
H51—C5—H52 | 109.5 | C31—C32—H322 | 111.7 |
C5—C6—C7 | 110.9 (2) | C33—C32—H322 | 107.5 |
C5—C6—H61 | 113.0 | H321—C32—H322 | 109.5 |
C7—C6—H61 | 107.6 | C28—C33—C32 | 110.82 (19) |
C5—C6—H62 | 107.0 | C28—C33—H331 | 107.9 |
C7—C6—H62 | 108.8 | C32—C33—H331 | 108.3 |
H61—C6—H62 | 109.5 | C28—C33—H332 | 111.4 |
C6—C7—C8 | 110.8 (2) | C32—C33—H332 | 110.8 |
C6—C7—H71 | 112.1 | H331—C33—H332 | 107.5 |
C8—C7—H71 | 106.9 | P25—N34—H341 | 118.9 |
C6—C7—H72 | 109.7 | C35—N34—H341 | 116.5 |
C8—C7—H72 | 107.7 | N34—C35—C36 | 117.6 (5) |
H71—C7—H72 | 109.5 | N34—C35—C40 | 106.3 (5) |
C9—C8—C7 | 110.1 (7) | C36—C35—C40 | 114.2 (6) |
C9—C8—H81 | 111.8 | N34—C35—H351 | 106.6 |
C7—C8—H81 | 115.3 | C36—C35—H351 | 102.0 |
C9—C8—H82 | 102.4 | C40—C35—H351 | 109.8 |
C7—C8—H82 | 106.9 | C35—C36—C37 | 110.71 (19) |
H81—C8—H82 | 109.5 | C35—C36—H361 | 106.4 |
P1—N10—H101 | 119.3 | C37—C36—H361 | 109.5 |
C11—N10—H101 | 119.1 | C35—C36—H362 | 110.6 |
N10—C11—C12 | 110.5 (5) | C37—C36—H362 | 110.1 |
N10—C11—C16 | 118.3 (5) | H361—C36—H362 | 109.5 |
C12—C11—C16 | 103.5 (7) | C36—C37—C38 | 110.8 (2) |
N10—C11—H111 | 108.1 | C36—C37—H371 | 109.5 |
C12—C11—H111 | 109.4 | C38—C37—H371 | 107.8 |
C16—C11—H111 | 106.7 | C36—C37—H372 | 107.8 |
C11—C12—C13 | 122.2 (8) | C38—C37—H372 | 111.5 |
C11—C12—H121 | 102.8 | H371—C37—H372 | 109.5 |
C13—C12—H121 | 108.9 | C37—C38—C39 | 110.8 (2) |
C11—C12—H122 | 108.7 | C37—C38—H381 | 108.0 |
C13—C12—H122 | 104.4 | C39—C38—H381 | 104.2 |
H121—C12—H122 | 109.5 | C37—C38—H382 | 107.9 |
C12—C13—C14 | 110.5 (2) | C39—C38—H382 | 116.1 |
C12—C13—H131 | 106.4 | H381—C38—H382 | 109.5 |
C14—C13—H131 | 109.2 | C38—C39—C40 | 110.9 (2) |
C12—C13—H132 | 110.1 | C38—C39—H391 | 106.9 |
C14—C13—H132 | 111.0 | C40—C39—H391 | 110.7 |
H131—C13—H132 | 109.5 | C38—C39—H392 | 104.1 |
C13—C14—C15 | 110.8 (2) | C40—C39—H392 | 114.3 |
C13—C14—H141 | 108.4 | H391—C39—H392 | 109.5 |
C15—C14—H141 | 114.6 | C35—C40—C39 | 111.1 (2) |
C13—C14—H142 | 107.6 | C35—C40—H401 | 106.6 |
C15—C14—H142 | 105.8 | C39—C40—H401 | 101.6 |
H141—C14—H142 | 109.5 | C35—C40—H402 | 114.2 |
C14—C15—C16 | 117.5 (10) | C39—C40—H402 | 112.8 |
C14—C15—H151 | 106.3 | H401—C40—H402 | 109.5 |
C16—C15—H151 | 112.4 | C42—N41—C48 | 115.3 (4) |
C14—C15—H152 | 109.4 | N41—C42—C43 | 110.4 (4) |
C16—C15—H152 | 101.6 | N41—C42—C47 | 112.8 (4) |
H151—C15—H152 | 109.5 | C43—C42—C47 | 111.4 (5) |
C15—C16—C11 | 112.8 (7) | N41—C42—H421 | 106.1 |
C15—C16—H161 | 106.0 | C43—C42—H421 | 108.1 |
C11—C16—H161 | 108.5 | C47—C42—H421 | 107.7 |
C15—C16—H162 | 110.9 | C42—C43—C44 | 108.5 (5) |
C11—C16—H162 | 109.0 | C42—C43—H431 | 110.8 |
H161—C16—H162 | 109.5 | C44—C43—H431 | 109.6 |
C18—N17—C24 | 119.7 (4) | C42—C43—H432 | 109.7 |
N17—C18—C19 | 111.5 (4) | C44—C43—H432 | 108.8 |
N17—C18—C23 | 114.0 (4) | H431—C43—H432 | 109.5 |
C19—C18—C23 | 109.6 (4) | C43—C44—C45 | 113.4 (6) |
N17—C18—H181 | 107.3 | C43—C44—H442 | 108.3 |
C19—C18—H181 | 107.6 | C45—C44—H442 | 108.1 |
C23—C18—H181 | 106.6 | C43—C44—H441 | 109.9 |
C18—C19—C20 | 108.7 (5) | C45—C44—H441 | 107.8 |
C18—C19—H191 | 110.2 | H442—C44—H441 | 109.1 |
C20—C19—H191 | 110.2 | C44—C45—C46 | 111.8 (5) |
C18—C19—H192 | 109.2 | C44—C45—H451 | 108.5 |
C20—C19—H192 | 109.0 | C46—C45—H451 | 108.1 |
H191—C19—H192 | 109.5 | C44—C45—H452 | 111.0 |
C19—C20—C21 | 113.9 (6) | C46—C45—H452 | 108.0 |
C19—C20—H201 | 109.0 | H451—C45—H452 | 109.5 |
C21—C20—H201 | 109.1 | C45—C46—C47 | 110.2 (7) |
C19—C20—H202 | 108.7 | C45—C46—H461 | 112.1 |
C21—C20—H202 | 106.6 | C47—C46—H461 | 110.0 |
H201—C20—H202 | 109.5 | C45—C46—H462 | 107.3 |
C20—C21—C22 | 107.5 (5) | C47—C46—H462 | 107.8 |
C20—C21—H211 | 110.7 | H461—C46—H462 | 109.5 |
C22—C21—H211 | 108.2 | C46—C47—C42 | 111.3 (5) |
C20—C21—H212 | 110.2 | C46—C47—H471 | 108.9 |
C22—C21—H212 | 110.6 | C42—C47—H471 | 109.2 |
H211—C21—H212 | 109.5 | C46—C47—H472 | 108.3 |
C21—C22—C23 | 109.7 (6) | C42—C47—H472 | 109.6 |
C21—C22—H221 | 109.2 | H471—C47—H472 | 109.5 |
C23—C22—H221 | 109.2 | N41—C48—H481 | 108.7 |
C21—C22—H222 | 110.2 | N41—C48—H482 | 109.0 |
C23—C22—H222 | 109.1 | H481—C48—H482 | 109.5 |
H221—C22—H222 | 109.5 | N41—C48—H483 | 110.8 |
C22—C23—C18 | 113.0 (5) | H481—C48—H483 | 109.5 |
C22—C23—H231 | 108.8 | H482—C48—H483 | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N10—H101···O26 | 0.95 | 2.14 | 2.908 (11) | 137 (1) |
N27—H271···O2i | 0.86 | 2.10 | 2.913 (11) | 159 (2) |
N3—H31···O26 | 0.95 | 2.17 | 2.971 (11) | 142 (1) |
N34—H341···O2i | 0.95 | 2.16 | 2.984 (11) | 144 (1) |
Symmetry code: (i) x, y+1, z. |
C12H26N3OP | F(000) = 568 |
Mr = 259.33 | Dx = 1.140 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 4337 reflections |
a = 6.3318 (3) Å | θ = 2.2–28.8° |
b = 10.3065 (5) Å | µ = 0.17 mm−1 |
c = 23.1616 (10) Å | T = 175 K |
V = 1511.48 (13) Å3 | Prism, colourless |
Z = 4 | 0.43 × 0.34 × 0.25 mm |
Agilent Xcalibur (Sapphire3 Gemini) diffractometer | 3678 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2989 reflections with I > 2.0σ(I) |
Graphite monochromator | Rint = 0.071 |
Detector resolution: 16.0143 pixels mm-1 | θmax = 29.1°, θmin = 1.8° |
ω scans | h = −8→8 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | k = −11→13 |
Tmin = 0.918, Tmax = 1.000 | l = −29→30 |
13647 measured reflections |
Refinement on F2 | Hydrogen site location: difference Fourier map |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.049 | Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)2]2 Ai are: 0.167E + 04 0.247E + 04 0.143E + 04 638. 36.7 |
wR(F2) = 0.121 | (Δ/σ)max = 0.009 |
S = 0.97 | Δρmax = 0.47 e Å−3 |
3625 reflections | Δρmin = −0.36 e Å−3 |
161 parameters | Absolute structure: Flack (1983), 1519 Friedel-pairs |
6 restraints | Absolute structure parameter: −0.03 (16) |
Primary atom site location: other |
C12H26N3OP | V = 1511.48 (13) Å3 |
Mr = 259.33 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 6.3318 (3) Å | µ = 0.17 mm−1 |
b = 10.3065 (5) Å | T = 175 K |
c = 23.1616 (10) Å | 0.43 × 0.34 × 0.25 mm |
Agilent Xcalibur (Sapphire3 Gemini) diffractometer | 3678 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | 2989 reflections with I > 2.0σ(I) |
Tmin = 0.918, Tmax = 1.000 | Rint = 0.071 |
13647 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.121 | Δρmax = 0.47 e Å−3 |
S = 0.97 | Δρmin = −0.36 e Å−3 |
3625 reflections | Absolute structure: Flack (1983), 1519 Friedel-pairs |
161 parameters | Absolute structure parameter: −0.03 (16) |
6 restraints |
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1 K. Cosier, J. & Glazer, A·M., 1986. J. Appl. Cryst. 105–107. Absorption correction: CrysAlis PRO, Agilent Technologies, Version 1.171.36.24 (release 03–12-2012 CrysAlis171. NET) (compiled Dec 3 2012,18:21:49) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
Refinement. Friedif = 72.6 Estimated Friedel difference = 3.2602 f computed from scattering factors, including f-prime No of Reflections processed = 3011 No of Friedel Pairs found = 1210 No of Friedel Pairs used = 1210 No of Unpaired Reflections = 141 No of Centric Reflections = 450 Flack parameter obtained from original refinement Hooft parameter obtained with Flack x set to zero Reflections only used if /Fo+ - Fo-/ < 99999.00 * /Fc+ - Fc-/ Friedif = 72.64 Acta A63, (2007), 257–265 Flack & Shmueli (2007) recommend a value >200 for general structures and >80 for enantiopure crystals Flack Parameter & su −0.0287 0.1094 Hooft Parameter & su −0.0562 0.0971 Ton G & su 1.1123 0.1943 For an enantiopure material, there are 2 choices, P2 P2(correct) 1.0000 i.e. 0.100000E+01 If 50:50 twinning is possible, there are 3 choices, P3 P3(correct) 1.0000 i.e. 0.100000E+01 P3(rac-twin) 0.0000 i.e. 0.898414E-07 P3(inverse) 0.0000 i.e. 0.251084E-25 G 1.1123 G S·U. 0.1943 FLEQ −0.0562 FLEQ S·U. 0.0971 i.e. 0.971323E-01 |
x | y | z | Uiso*/Ueq | ||
P1 | 0.92222 (12) | 0.71433 (7) | 0.56767 (3) | 0.0199 | |
O2 | 0.9220 (4) | 0.8287 (2) | 0.52819 (8) | 0.0261 | |
N3 | 1.0803 (5) | 0.6007 (2) | 0.54533 (11) | 0.0284 | |
C4 | 1.0607 (5) | 0.4687 (3) | 0.56811 (14) | 0.0280 | |
C5 | 0.8327 (5) | 0.4184 (3) | 0.56513 (14) | 0.0280 | |
C6 | 0.6864 (5) | 0.5142 (3) | 0.59713 (13) | 0.0263 | |
N7 | 0.6874 (4) | 0.6472 (2) | 0.57413 (10) | 0.0219 | |
H71 | 0.611 (4) | 0.654 (2) | 0.5442 (9) | 0.0279* | |
H62 | 0.7322 | 0.5169 | 0.6370 | 0.0309* | |
H61 | 0.5436 | 0.4800 | 0.5953 | 0.0305* | |
C8 | 0.7623 (7) | 0.4021 (3) | 0.50247 (14) | 0.0390 | |
H81 | 0.6146 | 0.3761 | 0.5016 | 0.0590* | |
H83 | 0.7765 | 0.4823 | 0.4819 | 0.0586* | |
H82 | 0.8467 | 0.3351 | 0.4840 | 0.0584* | |
C9 | 0.8230 (6) | 0.2877 (4) | 0.59695 (16) | 0.0424 | |
H91 | 0.6832 | 0.2537 | 0.5953 | 0.0619* | |
H93 | 0.8637 | 0.2983 | 0.6370 | 0.0615* | |
H92 | 0.9168 | 0.2268 | 0.5790 | 0.0614* | |
H41 | 1.1096 | 0.4682 | 0.6077 | 0.0328* | |
H42 | 1.1498 | 0.4124 | 0.5455 | 0.0330* | |
H31 | 1.180 (4) | 0.6198 (19) | 0.5226 (13) | 0.0344* | |
N10 | 0.9891 (4) | 0.7447 (2) | 0.63597 (10) | 0.0231 | |
C11 | 0.8364 (5) | 0.8141 (3) | 0.67295 (12) | 0.0234 | |
C12 | 0.8545 (6) | 0.9622 (3) | 0.66928 (13) | 0.0337 | |
C13 | 0.6835 (7) | 1.0266 (4) | 0.70579 (16) | 0.0426 | |
C14 | 0.6949 (7) | 0.9818 (4) | 0.76827 (15) | 0.0414 | |
C15 | 0.6814 (7) | 0.8348 (4) | 0.77232 (14) | 0.0390 | |
C16 | 0.8514 (6) | 0.7691 (3) | 0.73561 (12) | 0.0338 | |
H161 | 0.9865 | 0.7934 | 0.7513 | 0.0409* | |
H162 | 0.8370 | 0.6769 | 0.7374 | 0.0406* | |
H151 | 0.6950 | 0.8076 | 0.8123 | 0.0458* | |
H152 | 0.5447 | 0.8065 | 0.7587 | 0.0458* | |
H142 | 0.8293 | 1.0098 | 0.7850 | 0.0501* | |
H141 | 0.5801 | 1.0213 | 0.7897 | 0.0500* | |
H132 | 0.7055 | 1.1195 | 0.7040 | 0.0509* | |
H131 | 0.5484 | 1.0039 | 0.6894 | 0.0511* | |
H121 | 0.9968 | 0.9891 | 0.6835 | 0.0407* | |
H122 | 0.8426 | 0.9882 | 0.6298 | 0.0412* | |
H111 | 0.6979 | 0.7906 | 0.6591 | 0.0276* | |
C17 | 1.2130 (5) | 0.7761 (4) | 0.64523 (14) | 0.0333 | |
H172 | 1.2467 | 0.7705 | 0.6860 | 0.0495* | |
H171 | 1.2452 | 0.8605 | 0.6321 | 0.0499* | |
H173 | 1.2977 | 0.7152 | 0.6242 | 0.0497* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0209 (3) | 0.0218 (3) | 0.0168 (3) | 0.0006 (3) | 0.0010 (3) | 0.0003 (3) |
O2 | 0.0295 (11) | 0.0273 (10) | 0.0215 (9) | −0.0008 (9) | 0.0003 (9) | 0.0045 (8) |
N3 | 0.0313 (13) | 0.0243 (12) | 0.0296 (12) | 0.0006 (12) | 0.0140 (12) | 0.0031 (10) |
C4 | 0.0316 (15) | 0.0251 (13) | 0.0273 (13) | 0.0045 (12) | 0.0057 (15) | 0.0028 (13) |
C5 | 0.0359 (16) | 0.0228 (13) | 0.0253 (14) | −0.0007 (12) | 0.0002 (14) | 0.0041 (13) |
C6 | 0.0304 (16) | 0.0259 (15) | 0.0226 (13) | −0.0043 (12) | 0.0026 (12) | 0.0022 (12) |
N7 | 0.0214 (11) | 0.0264 (12) | 0.0180 (11) | 0.0016 (9) | −0.0005 (9) | −0.0009 (10) |
C8 | 0.054 (2) | 0.0305 (17) | 0.0325 (16) | 0.0012 (16) | −0.0032 (16) | −0.0087 (14) |
C9 | 0.047 (2) | 0.0307 (17) | 0.050 (2) | −0.0035 (17) | 0.0078 (17) | 0.0116 (17) |
N10 | 0.0242 (12) | 0.0262 (12) | 0.0187 (11) | 0.0014 (9) | −0.0023 (9) | −0.0002 (9) |
C11 | 0.0277 (14) | 0.0245 (15) | 0.0181 (12) | −0.0026 (11) | −0.0006 (11) | −0.0010 (10) |
C12 | 0.052 (2) | 0.0248 (15) | 0.0240 (15) | 0.0014 (14) | 0.0090 (14) | 0.0006 (12) |
C13 | 0.056 (2) | 0.0323 (18) | 0.0397 (19) | 0.0076 (17) | 0.0088 (18) | −0.0080 (16) |
C14 | 0.052 (2) | 0.041 (2) | 0.0308 (17) | −0.0116 (17) | 0.0112 (16) | −0.0142 (15) |
C15 | 0.052 (2) | 0.0429 (19) | 0.0221 (15) | −0.0140 (17) | 0.0081 (15) | −0.0032 (14) |
C16 | 0.0471 (19) | 0.0346 (17) | 0.0196 (13) | −0.0011 (15) | 0.0002 (13) | 0.0051 (12) |
C17 | 0.0251 (15) | 0.0410 (18) | 0.0339 (16) | −0.0033 (14) | −0.0062 (12) | −0.0017 (15) |
P1—O2 | 1.492 (2) | N10—C11 | 1.476 (4) |
P1—N3 | 1.625 (3) | N10—C17 | 1.470 (4) |
P1—N7 | 1.647 (3) | C11—C12 | 1.534 (4) |
P1—N10 | 1.667 (2) | C11—C16 | 1.527 (4) |
N3—C4 | 1.464 (3) | C11—H111 | 0.965 |
N3—H31 | 0.845 (18) | C12—C13 | 1.525 (5) |
C4—C5 | 1.536 (5) | C12—H121 | 0.999 |
C4—H41 | 0.969 | C12—H122 | 0.955 |
C4—H42 | 0.964 | C13—C14 | 1.521 (5) |
C5—C6 | 1.544 (4) | C13—H132 | 0.968 |
C5—C8 | 1.527 (4) | C13—H131 | 0.965 |
C5—C9 | 1.537 (4) | C14—C15 | 1.521 (5) |
C6—N7 | 1.471 (4) | C14—H142 | 0.978 |
C6—H62 | 0.968 | C14—H141 | 0.970 |
C6—H61 | 0.971 | C15—C16 | 1.529 (5) |
N7—H71 | 0.850 (17) | C15—H151 | 0.972 |
C8—H81 | 0.973 | C15—H152 | 0.967 |
C8—H83 | 0.958 | C16—H161 | 0.963 |
C8—H82 | 0.972 | C16—H162 | 0.955 |
C9—H91 | 0.953 | C17—H172 | 0.970 |
C9—H93 | 0.968 | C17—H171 | 0.944 |
C9—H92 | 0.958 | C17—H173 | 0.958 |
O2—P1—N3 | 112.03 (13) | C11—N10—C17 | 116.1 (2) |
O2—P1—N7 | 112.76 (13) | N10—C11—C12 | 113.7 (3) |
N3—P1—N7 | 106.39 (14) | N10—C11—C16 | 111.3 (2) |
P1—N3—C4 | 120.2 (2) | C12—C11—C16 | 110.5 (2) |
P1—N10—C11 | 118.37 (19) | N10—C11—H111 | 106.3 |
O2—P1—N10 | 115.69 (12) | C12—C11—H111 | 107.4 |
N3—P1—N10 | 106.32 (14) | C16—C11—H111 | 107.3 |
N7—P1—N10 | 102.82 (13) | C11—C12—C13 | 110.5 (3) |
C6—N7—P1 | 115.3 (2) | C11—C12—H121 | 109.0 |
P1—N10—C17 | 115.1 (2) | C13—C12—H121 | 109.7 |
P1—N3—H31 | 119.3 (12) | C11—C12—H122 | 109.0 |
C4—N3—H31 | 120.3 (13) | C13—C12—H122 | 110.7 |
N3—C4—C5 | 112.2 (3) | H121—C12—H122 | 108.0 |
N3—C4—H41 | 108.6 | C12—C13—C14 | 111.2 (3) |
C5—C4—H41 | 110.0 | C12—C13—H132 | 107.7 |
N3—C4—H42 | 108.3 | C14—C13—H132 | 109.6 |
C5—C4—H42 | 108.8 | C12—C13—H131 | 107.8 |
H41—C4—H42 | 108.9 | C14—C13—H131 | 110.0 |
C4—C5—C6 | 109.0 (2) | H132—C13—H131 | 110.5 |
C4—C5—C8 | 110.7 (3) | C13—C14—C15 | 111.0 (3) |
C6—C5—C8 | 110.6 (3) | C13—C14—H142 | 109.2 |
C4—C5—C9 | 108.2 (3) | C15—C14—H142 | 108.5 |
C6—C5—C9 | 107.9 (3) | C13—C14—H141 | 108.9 |
C8—C5—C9 | 110.4 (3) | C15—C14—H141 | 110.2 |
C5—C6—N7 | 114.8 (2) | H142—C14—H141 | 109.0 |
C5—C6—H62 | 107.3 | C14—C15—C16 | 111.6 (3) |
N7—C6—H62 | 108.5 | C14—C15—H151 | 109.9 |
C5—C6—H61 | 107.8 | C16—C15—H151 | 109.9 |
N7—C6—H61 | 109.0 | C14—C15—H152 | 109.3 |
H62—C6—H61 | 109.3 | C16—C15—H152 | 108.3 |
C6—N7—H71 | 111.8 (14) | H151—C15—H152 | 107.7 |
P1—N7—H71 | 114.0 (14) | C15—C16—C11 | 110.5 (3) |
C5—C8—H81 | 109.3 | C15—C16—H161 | 107.4 |
C5—C8—H83 | 110.5 | C11—C16—H161 | 109.6 |
H81—C8—H83 | 108.4 | C15—C16—H162 | 110.4 |
C5—C8—H82 | 109.6 | C11—C16—H162 | 109.8 |
H81—C8—H82 | 108.9 | H161—C16—H162 | 109.1 |
H83—C8—H82 | 110.1 | N10—C17—H172 | 110.0 |
C5—C9—H91 | 109.9 | N10—C17—H171 | 111.3 |
C5—C9—H93 | 110.5 | H172—C17—H171 | 108.7 |
H91—C9—H93 | 109.1 | N10—C17—H173 | 108.8 |
C5—C9—H92 | 110.0 | H172—C17—H173 | 109.4 |
H91—C9—H92 | 108.5 | H171—C17—H173 | 108.6 |
H93—C9—H92 | 108.9 |
D—H···A | D—H | H···A | D···A | D—H···A |
N7—H71···O2i | 0.85 | 2.07 | 2.916 (5) | 180 (3) |
N3—H31···O2ii | 0.85 | 2.00 | 2.848 (5) | 177 (3) |
Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) x+1/2, −y+3/2, −z+1. |
Experimental details
(I) | (II) | (III) | (IV) | |
Crystal data | ||||
Chemical formula | C17H36N3OP | C20H34N3OP | C19H38N3OP2 | C12H26N3OP |
Mr | 329.45 | 363.47 | 355.51 | 259.33 |
Crystal system, space group | Monoclinic, P21 | Monoclinic, P21/c | Orthorhombic, Pna21 | Orthorhombic, P212121 |
Temperature (K) | 175 | 175 | 175 | 175 |
a, b, c (Å) | 11.9879 (4), 19.1972 (6), 17.0720 (6) | 10.9207 (4), 24.0557 (7), 24.3993 (8) | 21.9179 (10), 8.9546 (4), 20.3544 (14) | 6.3318 (3), 10.3065 (5), 23.1616 (10) |
α, β, γ (°) | 90, 90.542 (3), 90 | 90, 98.980 (3), 90 | 90, 90, 90 | 90, 90, 90 |
V (Å3) | 3928.67 (14) | 6331.3 (4) | 3994.9 (3) | 1511.48 (13) |
Z | 8 | 12 | 8 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.15 | 0.14 | 0.15 | 0.17 |
Crystal size (mm) | 0.45 × 0.35 × 0.30 | 0.45 × 0.35 × 0.32 | 0.35 × 0.35 × 0.18 | 0.43 × 0.34 × 0.25 |
Data collection | ||||
Diffractometer | Oxford Diffraction Gemini | Agilent Xcalibur (Sapphire3, Gemini) | Oxford Diffraction Gemini | Agilent Xcalibur (Sapphire3 Gemini) |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2011) | Multi-scan (CrysAlis PRO; Agilent, 2011) | ψ scan (CrysAlis PRO; Agilent, 2011) | Multi-scan (CrysAlis PRO; Agilent, 2011) |
Tmin, Tmax | 0.95, 0.96 | 0.915, 1.000 | 0.95, 0.97 | 0.918, 1.000 |
No. of measured, independent and observed [I > 2.0σ(I)] reflections | 43414, 18366, 14523 | 44340, 14733, 10640 | 33932, 9291, 6779 | 13647, 3678, 2989 |
Rint | 0.064 | 0.047 | 0.050 | 0.071 |
(sin θ/λ)max (Å−1) | 0.688 | 0.684 | 0.682 | 0.683 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.096, 0.118, 1.09 | 0.058, 0.152, 0.90 | 0.124, 0.326, 1.22 | 0.049, 0.121, 0.97 |
No. of reflections | 17831 | 13613 | 8783 | 3625 |
No. of parameters | 883 | 694 | 437 | 161 |
No. of restraints | 141 | 18 | 444 | 6 |
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 |
Δρmax, Δρmin (e Å−3) | 1.77, −0.83 | 0.41, −0.40 | 2.27, −0.55 | 0.47, −0.36 |
Absolute structure | Flack (1983), 9230 Friedel pairs | ? | Flack (1983), 4252 Friedel-pairs | Flack (1983), 1519 Friedel-pairs |
Absolute structure parameter | −0.08 (10) | ? | 0.3 (2) | −0.03 (16) |
Computer programs: GEMINI (Oxford Diffraction, 2006), CrysAlis PRO (Agilent, 2011), SUPERFLIP (Palatinus & Chapuis, 2007), SUPERFLIP (Palatinus & Chapuis, 2007), PLATON (Spek, 2009) and Mercury (Macrae et al., 2008), CRYSTALS (Betteridge et al., 2003) and enCIFer (Allen et al., 2004).
P101—O102 | 1.487 (3) | P301—O302 | 1.475 (4) |
P101—N103 | 1.664 (4) | P301—N303 | 1.653 (4) |
P101—N111 | 1.623 (4) | P301—N311 | 1.635 (4) |
P101—N116 | 1.608 (5) | P301—N316 | 1.621 (4) |
P201—O202 | 1.490 (4) | P401—O402 | 1.493 (3) |
P201—N203 | 1.697 (4) | P401—N403 | 1.643 (4) |
P201—N211 | 1.595 (4) | P401—N411 | 1.631 (4) |
P201—N216 | 1.617 (5) | P401—N416 | 1.639 (4) |
O102—P101—N103 | 107.3 (2) | O302—P301—N303 | 107.0 (2) |
O102—P101—N111 | 112.2 (2) | O302—P301—N311 | 115.5 (2) |
N103—P101—N111 | 114.7 (2) | N303—P301—N311 | 110.0 (2) |
O102—P101—N116 | 116.5 (2) | O302—P301—N316 | 114.9 (2) |
N103—P101—N116 | 104.8 (2) | N303—P301—N316 | 110.0 (2) |
N111—P101—N116 | 101.4 (2) | N311—P301—N316 | 99.4 (2) |
O202—P201—N203 | 107.8 (2) | O402—P401—N403 | 107.88 (19) |
O202—P201—N211 | 112.6 (2) | O402—P401—N411 | 113.7 (2) |
N203—P201—N211 | 113.9 (2) | N403—P401—N411 | 112.6 (2) |
O202—P201—N216 | 116.8 (2) | O402—P401—N416 | 116.5 (2) |
N203—P201—N216 | 104.3 (2) | N403—P401—N416 | 106.1 (2) |
N211—P201—N216 | 101.3 (2) | N411—P401—N416 | 99.7 (2) |
P101—N103—C104 | 120.8 (4) | P101—N103—C105 | 118.4 (3) |
P101—N111—C112 | 128.4 (4) | P101—N116—C117 | 130.0 (4) |
P201—N203—C204 | 118.3 (4) | P201—N203—C205 | 119.5 (3) |
P201—N216—C217 | 127.1 (4) | P201—N211—C212 | 128.7 (4) |
P301—N303—C304 | 119.0 (3) | P301—N303—C305 | 123.6 (3) |
P301—N311—C312 | 128.6 (2) | P301—N316—C317 | 124.1 (4) |
P401—N403—C404 | 118.9 (3) | P401—N403—C405 | 124.2 (3) |
P401—N411—C412 | 129.0 (3) | P401—N416—C417 | 125.4 (3) |
P1—O2 | 1.4818 (17) | P26—N35 | 1.644 (2) |
P1—N3 | 1.641 (2) | P26—N43 | 1.637 (2) |
P1—N11 | 1.630 (2) | P51—O52 | 1.4857 (17) |
P1—N18 | 1.653 (2) | P51—N53 | 1.639 (2) |
P26—O27 | 1.4876 (17) | P51—N61 | 1.647 (2) |
P26—N28 | 1.632 (2) | P51—N69 | 1.627 (2) |
O2—P1—N3 | 107.28 (10) | P51—N61—C62 | 128.63 (17) |
O2—P1—N11 | 117.13 (11) | O27—P26—N43 | 107.42 (10) |
N3—P1—N11 | 107.76 (11) | N28—P26—N43 | 111.66 (11) |
O2—P1—N18 | 114.30 (11) | N35—P26—N43 | 108.07 (11) |
N3—P1—N18 | 111.20 (11) | O52—P51—N53 | 107.09 (10) |
N11—P1—N18 | 98.92 (10) | O52—P51—N61 | 115.30 (11) |
O27—P26—N28 | 114.51 (11) | N53—P51—N61 | 110.55 (11) |
O27—P26—N35 | 116.58 (11) | P1—N3—C10 | 120.27 (17) |
N28—P26—N35 | 98.36 (10) | P1—N18—C19 | 128.23 (17) |
P1—N3—C4 | 120.31 (15) | P26—N35—C36 | 128.78 (17) |
P1—N11—C12 | 122.88 (16) | P26—N43—C50 | 118.53 (17) |
P26—N28—C29 | 123.66 (16) | P51—N53—C54 | 119.54 (16) |
P26—N43—C44 | 121.82 (15) | P51—N69—C70 | 122.79 (17) |
P51—N53—C60 | 120.33 (18) |
P1—O2 | 1.478 (4) | P25—O26 | 1.520 (4) |
P1—N3 | 1.608 (5) | P25—N27 | 1.619 (5) |
P1—N10 | 1.680 (5) | P25—N34 | 1.677 (5) |
P1—N17 | 1.667 (4) | P25—N41 | 1.635 (4) |
O2—P1—N3 | 120.6 (3) | O26—P25—N27 | 115.7 (3) |
O2—P1—N10 | 115.9 (3) | O26—P25—N34 | 114.8 (2) |
N3—P1—N10 | 99.1 (2) | N27—P25—N34 | 99.4 (2) |
O2—P1—N17 | 106.44 (19) | O26—P25—N41 | 108.9 (2) |
N3—P1—N17 | 106.5 (3) | N27—P25—N41 | 109.3 (2) |
N10—P1—N17 | 107.4 (2) | N34—P25—N41 | 108.2 (3) |
P1—N3—C4 | 123.4 (4) | P1—N10—C11 | 121.6 (4) |
P1—N17—C24 | 117.7 (4) | P1—N17—C18 | 122.3 (3) |
P25—N27—C28 | 121.2 (4) | P25—N34—C35 | 124.0 (4) |
P25—N41—C48 | 121.0 (3) | P25—N41—C42 | 123.4 (4) |
P1—O2 | 1.492 (2) | P1—N7 | 1.647 (3) |
P1—N3 | 1.625 (3) | P1—N10 | 1.667 (2) |
O2—P1—N3 | 112.03 (13) | O2—P1—N10 | 115.69 (12) |
O2—P1—N7 | 112.76 (13) | N3—P1—N10 | 106.32 (14) |
N3—P1—N7 | 106.39 (14) | N7—P1—N10 | 102.82 (13) |
P1—N3—C4 | 120.2 (2) | C6—N7—P1 | 115.3 (2) |
P1—N10—C11 | 118.37 (19) | P1—N10—C17 | 115.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N111—H1111···O302i | 0.840 | 2.064 | 2.896 (11) | 170.3 (20) |
N211—H2111···O402ii | 0.846 | 2.072 | 2.873 (11) | 158 (4) |
N216—H2161···O402ii | 0.843 | 2.293 | 3.062 (11) | 152 (2) |
N311—H3111···O202 | 0.854 | 2.080 | 2.914 (11) | 165 (3) |
C3142—H3147···O302 | 0.960 | 2.403 | 3.155 (11) | 134.92 (18) |
N316—H3161···O202 | 0.851 | 2.282 | 3.086 (11) | 157.6 (13) |
N411—H4111···O102 | 0.850 | 2.106 | 2.915 (11) | 159 (4) |
N416—H4161···O102 | 0.838 | 2.495 | 3.118 (11) | 132 (4) |
Symmetry codes: (i) −x+1, y+1/2, −z; (ii) −x+1, y−1/2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H111···O27 | 0.842 | 2.109 | 2.908 (4) | 158.2 (16) |
N18—H181···O27 | 0.865 | 1.981 | 2.813 (4) | 161 (2) |
C63—H631···O52 | 0.939 | 2.564 | 3.225 (4) | 127.69 (7) |
N61—H611···O2i | 0.845 | 2.008 | 2.838 (4) | 167.0 (18) |
N69—H691···O2i | 0.855 | 2.093 | 2.907 (4) | 159.1 (16) |
N35—H351···O52ii | 0.841 | 2.003 | 2.819 (4) | 163.2 (17) |
N28—H281···O52ii | 0.831 | 2.049 | 2.854 (4) | 163.1 (16) |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N10—H101···O26 | 0.950 | 2.138 | 2.908 (11) | 137.24 (15) |
N27—H271···O2i | 0.859 | 2.095 | 2.913 (11) | 159.0 (19) |
N3—H31···O26 | 0.950 | 2.167 | 2.971 (11) | 141.66 (16) |
N34—H341···O2i | 0.950 | 2.162 | 2.984 (11) | 144.14 (17) |
Symmetry code: (i) x, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N7—H71···O2i | 0.850 | 2.066 | 2.916 (5) | 180 (3) |
N3—H31···O2ii | 0.845 | 2.004 | 2.848 (5) | 177 (3) |
Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) x+1/2, −y+3/2, −z+1. |
Subscribe to Acta Crystallographica Section C: Structural Chemistry
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- Purchase subscription
- Reduced-price subscriptions
- If you have already subscribed, you may need to register