Syntheses and structures of four new mixed-amide phospho­ric tri­amides

Keikha, M.; Pourayoubi, M.; Tarahhomi, A.; Lee, A. van der

doi:10.1107/S2053229616001595

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Syntheses and structures of four new mixed-amide phosphoric triamides

M. Keikha, M. Pourayoubi, A. Tarahhomi and A. van der Lee

Phosphoric triamides have extensive applications in biochemistry and are also used as O-donor ligands. Four new mixed-amide phosphoric triamide structures, namely rac-N-tert-butyl-N′,N′′-dicyclohexyl-N′′-methylphosphoric triamide, C₁₇H₃₆N₃OP, (I), rac-N,N′-dicyclohexyl-N′-methyl-N′′-(p-tolyl)phosphoric triamide, C₂₀H₃₄N₃OP, (II), N,N′,N′′-tricyclohexyl-N′′-methylphosphoric triamide, C₁₉H₃₈N₃OP, (III), and 2-[cyclohexyl(methyl)amino]-5,5-dimethyl-1,3,2λ⁵-diazaphosphinan-2-one, C₁₂H₂₆N₃OP, (IV), have been synthesized and studied by X-ray diffraction and spectroscopic methods. Structures (I) and (II) are the first diffraction studies of acyclic racemic mixed-amide phosphoric triamides. The P—N bonds resulting from the different substituent –N(CH₃)(C₆H₁₁), (C₆H₁₁)NH–, 4-CH₃-C₆H₄NH–, (tert-C₄H₉)NH– and –NHCH₂C(CH₃)₂CH₂NH– groups are compared, along with the different molecular volumes and electron-donor strengths. In all four structures, the molecules form extended chains through N—H

O hydrogen bonds.

Keywords: mixed-amide phosphoric triamide; racemic; crystal structure; N—H

O hydrogen bond; NMR experiment.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616001595/fp3025sup1.cif Contains datablocks I, II, III, IV, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616001595/fp3025Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616001595/fp3025Isup6.cml Supplementary material
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616001595/fp3025IIsup3.hkl Contains datablock 1
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616001595/fp3025IIsup7.cml Supplementary material
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616001595/fp3025IIIsup4.hkl Contains datablock 1
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616001595/fp3025IIIsup8.cml Supplementary material
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616001595/fp3025IVsup5.hkl Contains datablock 1
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616001595/fp3025IVsup9.cml Supplementary material
	Portable Document Format (PDF) file https://doi.org/10.1107/S2053229616001595/fp3025sup10.pdf MS and NMR spectra for compounds (I)–(IV)

CCDC references: 1449952; 1449951; 1449950; 1449949

Introduction top

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 –NR^xR^y groups (R^x ≠ H; R^y = 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] (R^1–3 = 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 NR^xR^y 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) [R^1–6 = H or a hydrocarbon segment, and NR¹R² ≠ NR³R⁴ ≠ NR⁵R⁶], which are also referred to as mixed triamide phosphine oxides.

Experimental top

Synthesis and crystallization top

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, 13}C NMR and MS spectra of compounds (I)–(IV) are given in Figs. S1–S15 in the Supporting information.

NMR, IR and MS analyses top

For (I) top

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, J_C–P = 5.3 Hz), 25.56 (s), 25.69 (s), 26.05 (s), 27.86 (d, J_C–P = 5.3 Hz), 28.91 (s), 29.75 (s) 31.75 (d, J_C–P = 4.5 Hz), 36.17 (d, J_C–P = 4.5 Hz), 36.32 (d, J_C–P = 5.3 Hz), 50.02 (s), 54.45 (d, J_C–P = 4.5 Hz).

For (II) top

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]^{+. 31}P{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, ²J_H–P = 7.8 Hz, 1H, NH), 6.91 (d, ³J_H–H = 8.4 Hz, 2H, Ar—H), 7.00 (d, ³J_H–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, J_C–P = 7.6 Hz), 25.46 (s), 25.61 (s), 26.00 (s), 27.72 (d, J_C–P = 5.3 Hz), 31.10 (d, J_C–P = 2.3 Hz), 36.12 (d, J_C–P = 6.1 Hz), 36.23 (d, J_C–P = 4.5 Hz), 50.01 (s), 54.72 (d, J_C–P = 3.8 Hz), 117.74 (d, J_C–P) = 6.8 Hz), 129.50 (s), 129.92 (s), 138.74 (s).

For (III) top

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]^{+. 31}P{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, ³J_H–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, J_C–P = 3.0 Hz), 25.49 (s), 25.63 (s), 25.97 (s), 27.72 (d, J_C–P = 4.5 Hz), 31.18 (d, J_C–P = 2.3 Hz), 36.27 (d, J_C–P = 4.5 Hz), 36.50 (d, J_C–P = 4.5 Hz), 49.86 (s), 54.30 (d, J_C–P = 3.8 Hz).

For (IV) top

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]^{+. 31}P{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, ³J_H–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, J_C–P = 5.6 Hz), 31.19 (d, J_C–P = 3.6 Hz), 53.71 (d, J_C–P = 2.9 Hz), 53.82 (d, J_C–P = 3.5 Hz), 53.87 (s).

Refinement top

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 U_iso(H) = 1.5U_eq(C_i) for CH₃ groups or 1.2U_eq(C_ii) for CH₂ and CH groups, where U_eq(C_i) and U_eq(C_ii) 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 U_iso(H) = 1.2U_eq(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.

Results and discussion top

Synthesis top

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).

Structural features top

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.

Structure description top

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).

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.

Synthesis and crystallization top

Refinement details top

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.

Computing details top

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).

Figures top

	Fig. 1. Displacement ellipsoid plots (at the 50% probability level) of the components of the asymmetric unit of (I), showing the atom-numbering schemes. H atoms are drawn as spheres of arbitrary radii.
	Fig. 2. Displacement ellipsoid plots (at the 50% probability level) of the components of the asymmetric unit of (II), showing the atom-numbering schemes. H atoms are drawn as spheres of arbitrary radii.
	Fig. 3. Displacement ellipsoid plots (at the 50% probability level) of the components of the asymmetric unit of (III), showing the atom-numbering schemes. H atoms are drawn as spheres of arbitrary radii.
	Fig. 4. Displacement ellipsoids (at the 50% probability level) of (IV), showing the atom-numbering scheme. H atoms are drawn as spheres of arbitrary radii.
	Fig. 5. A partial view of the crystal packing of (I). The one-dimensional chain, containing four independent molecules (shown as different colours), is formed by (N—H···)₂O═P and (N—H···)O═P hydrogen bonds (black dashed lines) along the c axis building R₂¹(6) and C(4) motifs (with an ···R₂¹(6)R₂¹(6)C(4)C(4)R₂¹(6)R₂¹(6)C(4)C(4)··· arrangement). Only H atoms involved in hydrogen bonds are shown. The P(O)(NH) and P(O)(NH)₂ segments involved in hydrogen bonding are shown as `capped sticks'.
	Fig. 6. A partial view of the crystal packing of (II) in which the (N—H···)₂O═P hydrogen bonds (black dashed lines) connect symmetry-independent molecules into a one-dimensional chain along the a axis, forming an R₂¹(6) ring motif. The symmetry-independent molecules are shown as different colours (green, yellow and purple) and H atoms bonded to C atoms have been omitted for clarity. The P(O)(NH)₂ segments involved in hydrogen bonding are shown as `capped sticks'.
	Fig. 7. Part of the crystal packing of structure (III), showing the one-dimensional chain formed through (N—H···)₂O═P hydrogen bonds [building the R₂¹(6) ring motif] along the b axis. The hydrogen bonds are shown as black dashed lines, symmetry-independent molecules are given as different colours (yellow and purple), H atoms bonded to C atoms have been omitted for clarity and the P(O)(NH)₂ segments involved in hydrogen bonding are shown as `capped sticks'.
	Fig. 8. The extended one-dimensional chain arrangement of (IV) [containing the R₂²(8) ring motif] along the a axis, formed through the (N—H···)(N—H···)O═P hydrogen bonds. The hydrogen bonds are shown as black dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity and the P(O)(NH)₂ parts involved in hydrogen bonding are shown as `capped sticks'.

(I) rac-N-tert-Butyl-N',N''-dicyclohexyl-N''-methylphosphoric triamide top

Crystal data top

C₁₇H₃₆N₃OP	F(000) = 1456.000
M_r = 329.45	D_x = 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

Data collection top

Oxford Diffraction Gemini diffractometer	14523 reflections with I > 2.0σ(I)
Graphite monochromator	R_int = 0.064
ω scans	θ_max = 29.3°, θ_min = 1.6°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	h = −15→15
T_min = 0.95, T_max = 0.96	k = −26→25
43414 measured reflections	l = −23→22
18366 independent reflections

Refinement top

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/[A₀T₀(x) + A₁T₁(x) ··· + A_n-1]T_n-1(x)] where A_i are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] [1-(deltaF/6*sigmaF)²]² A_i are: 419. 494. 196.
wR(F²) = 0.118	(Δ/σ)_max = 0.009
S = 1.09	Δρ_max = 1.77 e Å⁻³
17831 reflections	Δρ_min = −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

Crystal data top

C₁₇H₃₆N₃OP	V = 3928.67 (14) Å³
M_r = 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)°

Data collection top

Oxford Diffraction Gemini diffractometer	18366 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	14523 reflections with I > 2.0σ(I)
T_min = 0.95, T_max = 0.96	R_int = 0.064
43414 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.096	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.118	Δρ_max = 1.77 e Å⁻³
S = 1.09	Δρ_min = −0.83 e Å⁻³
17831 reflections	Absolute structure: Flack (1983), 9230 Friedel pairs
883 parameters	Absolute structure parameter: −0.08 (10)
141 restraints

Special details top

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.

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

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

(II) rac-N,N'-Dicyclohexyl-N'-methyl-N''-(p-tolyl)phosphoric triamide top

Crystal data top

C₂₀H₃₄N₃OP	F(000) = 2376
M_r = 363.47	D_x = 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

Data collection top

Agilent Xcalibur (Sapphire3, Gemini) diffractometer	14733 independent reflections
Radiation source: Enhance (Mo) X-ray Source	10640 reflections with I > 2.0σ(I)
Graphite monochromator	R_int = 0.047
Detector resolution: 16.0143 pixels mm^-1	θ_max = 29.1°, θ_min = 1.7°
ω scans	h = −14→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −30→32
T_min = 0.915, T_max = 1.000	l = −33→31
44340 measured reflections

Refinement top

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/[A₀T₀(x) + A₁T₁(x) ··· + A_n-1]T_n-1(x)] where A_i are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] [1-(deltaF/6*sigmaF)²]² A_i are: 0.275E + 04 0.448E + 04 0.294E + 04 0.134E + 04 368.
S = 0.90	(Δ/σ)_max = 0.001
13613 reflections	Δρ_max = 0.41 e Å⁻³
694 parameters	Δρ_min = −0.40 e Å⁻³
18 restraints

Crystal data top

C₂₀H₃₄N₃OP	V = 6331.3 (4) Å³
M_r = 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)°

Data collection top

Agilent Xcalibur (Sapphire3, Gemini) diffractometer	14733 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	10640 reflections with I > 2.0σ(I)
T_min = 0.915, T_max = 1.000	R_int = 0.047
44340 measured reflections

Refinement top

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	Δρ_max = 0.41 e Å⁻³
13613 reflections	Δρ_min = −0.40 e Å⁻³
694 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

(III) N,N',N''-Tricyclohexyl-N''-methylphosphoric triamide top

Crystal data top

C₁₉H₃₈N₃OP₂	D_x = 1.182 Mg m⁻³
M_r = 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

Data collection top

Oxford Diffraction Gemini diffractometer	6779 reflections with I > 2.0σ(I)
Graphite monochromator	R_int = 0.050
ω scans	θ_max = 29.0°, θ_min = 1.9°
Absorption correction: ψ scan (CrysAlis PRO; Agilent, 2011)	h = −29→27
T_min = 0.95, T_max = 0.97	k = −11→12
33932 measured reflections	l = −25→26
9291 independent reflections

Refinement top

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(F_o²,0) + 2F_c²)/3
wR(F²) = 0.326	(Δ/σ)_max = 0.004
S = 1.22	Δρ_max = 2.27 e Å⁻³
8783 reflections	Δρ_min = −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

Crystal data top

C₁₉H₃₈N₃OP₂	V = 3994.9 (3) Å³
M_r = 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

Data collection top

Oxford Diffraction Gemini diffractometer	9291 independent reflections
Absorption correction: ψ scan (CrysAlis PRO; Agilent, 2011)	6779 reflections with I > 2.0σ(I)
T_min = 0.95, T_max = 0.97	R_int = 0.050
33932 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.124	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.326	Δρ_max = 2.27 e Å⁻³
S = 1.22	Δρ_min = −0.55 e Å⁻³
8783 reflections	Absolute structure: Flack (1983), 4252 Friedel-pairs
437 parameters	Absolute structure parameter: 0.3 (2)
444 restraints

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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.

(IV) 2-[Cyclohexyl(methyl)amino]-5,5-dimethyl-1,3,2λ⁵-diazaphosphinan-2-one top

Crystal data top

C₁₂H₂₆N₃OP	F(000) = 568
M_r = 259.33	D_x = 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

Data collection top

Agilent Xcalibur (Sapphire3 Gemini) diffractometer	3678 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2989 reflections with I > 2.0σ(I)
Graphite monochromator	R_int = 0.071
Detector resolution: 16.0143 pixels mm^-1	θ_max = 29.1°, θ_min = 1.8°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −11→13
T_min = 0.918, T_max = 1.000	l = −29→30
13647 measured reflections

Refinement top

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/[A₀T₀(x) + A₁T₁(x) ··· + A_n-1]T_n-1(x)] where A_i are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] [1-(deltaF/6*sigmaF)²]² A_i 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	Δρ_max = 0.47 e Å⁻³
3625 reflections	Δρ_min = −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

Crystal data top

C₁₂H₂₆N₃OP	V = 1511.48 (13) Å³
M_r = 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

Data collection top

Agilent Xcalibur (Sapphire3 Gemini) diffractometer	3678 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2989 reflections with I > 2.0σ(I)
T_min = 0.918, T_max = 1.000	R_int = 0.071
13647 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.121	Δρ_max = 0.47 e Å⁻³
S = 0.97	Δρ_min = −0.36 e Å⁻³
3625 reflections	Absolute structure: Flack (1983), 1519 Friedel-pairs
161 parameters	Absolute structure parameter: −0.03 (16)
6 restraints

Special details top

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 /F_o+ - F_o-/ < 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

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	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
R_int	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
Δρ_max, Δρ_min (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).

Selected geometric parameters (Å, º) for (I) top

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)

Selected geometric parameters (Å, º) for (II) top

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)

Selected geometric parameters (Å, º) for (III) top

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)

Selected geometric parameters (Å, º) for (IV) top

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)

Hydrogen-bond geometry (Å, º) for (I) top

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.

Hydrogen-bond geometry (Å, º) for (II) top

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.

Hydrogen-bond geometry (Å, º) for (III) top

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.

Hydrogen-bond geometry (Å, º) for (IV) top

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.

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Syntheses and structures of four new mixed-amide phospho­ric tri­amides

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Syntheses and structures of four new mixed-amide phosphoric triamides