Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615014527/fa3370sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615014527/fa3370Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615014527/fa3370IIsup3.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615014527/fa3370Isup4.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615014527/fa3370IIsup5.cml | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229615014527/fa3370sup6.pdf |
CCDC references: 1416438; 1416437
Three-dimensional Hirshfeld surfaces and the corresponding two-dimensional fingerprint maps are unique for each molecule/ion constituting the asymmetric unit of a crystal structure. They provide an easy means of comparing intermolecular contacts relative to van der Waals radii through a simple red–white–blue colour scheme (McKinnon, Jayatilaka & Spackman, 2007).
So far, this type of analysis has been applied to the study of different families of compounds, such as polymorphic systems in CS2 at low temperature (Dziubek & Katrusiak, 2004), piracetam (Fabbiani et al., 2005), R-glycylglycine (Moggach, Allan, Parsons & Sawyer, 2006), L-serine (Moggach, Marshall & Parsons, 2006), benzene (Budzianowski & Katrusiak, 2006), tetrathiafulvalene (McKinnon, Fabbiani & Spackman, 2007), naphthalene, phenanthrene and pyrene (Fabbiani et al., 2006) and a series of triarylcarbonyl derivatives (Bacchi et al., 2006). In addition, symmetry-independent molecules within one structure (Tarahhomi et al. 2013; Gholivand et al., 2015), cation–anion compounds (Gholizadeh et al., 2014; Ling et al., 2010) and cocrystals (Clausen et al., 2010) have also been studied by Hirshfeld surface analysis.
Recently, we have used this analysis to study intermolecular interactions in three different families of phosphoramides (phosphoric triamide, amidophosphoester and amidopyrophosphate) (Tarahhomi et al., 2013) and also in organotin(IV)–phosphoramide complexes (Pourayoubi, Shoghpour Bayraq et al., 2014). Such analysis has not been used to date for the study of phosphorothioic triamide compounds.
In this work, we present crystal structure analyses complemented by an investigation of molecular interactions for two new phosphorothioic triamide structures, i.e. P(S)[NHC6H3-3,4-(CH3)2]3.CH3CN, (I), and P(S)[NHC6H4(4-CH3)]3[3-CH3—C5H9NH2]+.Cl-, (II) (see Schemes 1 and 2, respectively).
A solution of 3,4-dimethylaniline (4.32 g, 35.76 mmol) in dry CH3CN (10 ml) was added dropwise to a solution of thiophosphoryl chloride (1.01 g, 5.96 mmol) in the same solvent (10 ml) under stirring at 273 K. After 3 h, the stirring was stopped and the mixture was transferred to a beaker which was kept at room temperature to evaporate the solvent. After a few days, the solid formed was washed with distilled water. White single crystals were obtained from a solution of the product in CH3CN/CHCl3 (3:1 v/v) by slow evaporation at room temperature. Yield > 70%. IR (KBr disc, ν, cm-1): 653, 810, 927, 980, 1017, 1059, 1119, 1181, 1229, 1280, 1381, 1457, 1513, 1616, 2937, 3182 (NH).
Compound (II) was obtained in an unsuccessful effort to prepare a mixed amido–phosphorothioic triamide from a reaction of thiophosphoryl chloride (0.500 g, 2.95 mmol) and p-toluidine (1.264 g, 11.80 mmol) in dry CH3CN (20 ml) at 273 K in the first step of the process. The solid formed was removed and then in the second step 3-methyl piperidine (0.585 g, 5.90 mmol) was added to the filtered solution under stirring at 273 K; the reaction time was 3 h per step. After stopping the second reaction, the mixture was transferred to a beaker to evaporate the solvent at room temperature. After a few days, the solid formed was washed with distilled water and dried. Crystals of (II) were obtained from a solution of the product in CH3OH/n-C7H16 (5:1 v/v) by slow evaporation at room temperature. Yield [relative to to P(S)Cl3] > 70%. IR (KBr disc, ν, cm-1): 652, 685, 762, 803, 888, 922, 1023, 1091, 1157, 1196, 1211, 1297, 1421, 1452, 1487, 1591, 2851, 2927, 3307 (NH).
The three-dimensional Hirshfeld surfaces (HSs), mapped with dnorm (Spackman & McKinnon, 2002) and two-dimensional fingerprint plots of structures (I) and (II) were generated using the Crystal Explorer software (Wolff et al., 2013).
Crystal data, data collection and structure refinement details are summarized in Table 1. For both structures, H atoms bonded to N atoms were found in difference Fourier maps and their coordinates were refined with a distance restraint N—H = 0.87 Å with a standatd uncertainty of 0.01 Å. All other H atoms in both structures were kept in their geometrically expected positions, with C—H = 0.96 Å. The isotropic atomic displacement parameters of the H atoms were evaluated as 1.2Ueq of the parent atom. In (II), two methyl groups bonded to aromatic rings were found to be disordered by rotation around the C—C axis. The disordered H-atom positions were clearly identified from difference Fourier maps. The occupancies for the two disordered positions were 0.51 (2) and 0.49 (2) for the methyl group at C7, and 0.40 (3) and 0.60 (3) for the methyl group at C14.
The asymmetric unit of (I) consists of two symmetry-independent phosphorothioic triamide molecules [(IA) and (IB) hereafter] and one acetonitrile (CH3CN) solvent molecule (Fig. 1), whereas, for (II), the asymmetric unit consists of one phosphorothioic triamide molecule, one 3-methylpiperidinium cation and one chloride anion (Fig. 2). Selected geometric parameters and hydrogen-bond geometries for (I) and (II) are given in Tables 2–5. In both structures, the P atoms are within a distorted tetrahedral P[S][N]3 environment with the bond angles ranging from 98.85 (9) (N1a—P1a—N3a) to 116.27 (7)° (S1a—P1a—N3a) for (IA), from 97.25 (10) (N1b—P1b—N2b) to 116.55 (8)° (S1b—P1b—N2b) for (IB), and from 97.91 (6) (N1—P1—N3) to 117.55 (4)° [S1—P1—N1] for (II).
The Pδb S and P—N bond lengths are within the ranges observed in analogous structures (Pourayoubi, Abrishami et al., 2014). The P—N—C angles, with values close to 120° show that the hybridization of the N atom is close to sp2. All N atoms in the structures (I) and (II) have almost planar geometry, except for atom N3a of molecule (IA). In this case, a slightly nonplanar geometry is found, reflected in the bond-angle sum at N3a [353.3 (2)°].
Moreover, the positions of atoms directly bonded to N3a suggest an anti orientation of the lone electron pair with respect to the Pδb S bond. This is similar to the recently published analysis of the Cambridge Structural Database (CSD, Version 5.35, updated in February 2014; Groom & Allen, 2014) for structures with a P(S)[N]3 fragment including nonplanar N atoms within a [P]N[X][Y] environment (X and Y are any atoms) (Raissi Shabari et al., 2015).
In the crystal structure of (I), two (IA) molecules and two (IB) molecules, together with two acetonitrile solvent molecules, form a six-molecule aggregate, as shown in Fig. 3. In this arrangement, the four phosphorothioic triamide molecules are hydrogen bonded to each other via N—H···S hydrogen bonds, forming R22(8) and R21(6) graph-set motifs (for the symbols defined for graph-set motifs, see Etter et al., 1990). The acetonitrile solvent molecules are linked at the two ends of this aggregate through N—H···N hydrogen bonds (Table 3), which accompany C—H···N interactions, forming R21(6) and R21(8) graph-set motifs.
In the crystal structure of (II), a two-dimensional arrangement parallel to the (101) plane is built from N—H···S and N—H···Cl hydrogen bonds involving the neutral molecules, cations and anions, as shown in Fig. 4. Within this pattern, two phosphorothioic triamide molecules and two cations form R22(4) graph-set motifs, through a Pδb S···[H—N]2 interaction with one N—H unit from each adjacent CH3—C5H9NH2+ cation. In this motif, we can distinguish two kinds of three-centred hydrogen bonding, i.e. S connected with two H-donor sites (double hydrogen-bond acceptor), and an N—H unit connected to two S atoms (bifurcated hydrogen bond). The other NH unit of the cation and all three NH units of the P(S)[NHC6H4(4-CH3)]3 molecule take part in N—H···Cl hydrogen bonds.
The three-dimensional HS generated for structures (I) and (II) are presented in Figs. 5 and 6, respectively. The contacts shown in red highlight the intermolecular interactions with distances closer than the sum of the van der Waals (vdW) radii, while white is used for contacts near the vdW separation, and blue represents longer contacts (McKinnon, Jayatilaka & Spackman, 2007).
For structure (I), the Hirshfeld surfaces are plotted separately for the two symmetry-independent phosphorothioic triamide molecules (Figs. 5a and 5b). In these maps, two different N—H···Sδb P hydrogen bonds, connecting molecules (IA) and (IB) to each other, appear as large red areas labelled 1 and 2. The other large red spots in Fig. 5a (labels 3 and 4) correspond to pairs of N—H···Sδb P hydrogen bonds between molecules (IA). On the other hand, molecule (IB) is also linked to the acetonitrile solvent molecule through N—H···N (labels 6 and 7) and C—H···N (label 8). These interactions are seen in Fig. 5(b) as large and small red areas, respectively, in accord with the strengths of the interactions.
Furthermore, it should be noted that the only remarkable H···C contact in structure (I) is related to the interaction of one methyl H atom [on the 3,4-(CH3)2C6H3NH fragment] in molecule (IB) with the aromatic ring of an adjacent molecule (IB) (C15b—H2c15b···C2b; label 9 in Fig. 5b) that is seen as a pale-red spot. The HS for the acetonitrile solvent molecule does not provide any further information and was not included.
Concerning the structure of (II), the Hirshfeld surfaces were generated for the P(S)[NHC6H4-4-CH3]3 molecule, for the 3-CH3—C5H9NH2+ cation and for the Cl- anion and are presented in Figs. 6(a), 6(b) and 6(c), respectively.
Three NH units of the phosphorothioic triamide molecule take part in different N—H···Cl hydrogen bonds with two neighbouring Cl- anions (labels 1–3 in Fig. 6a). These hydrogen bonds and the N—H···Cl hydrogen bond between the cation and the anion (which will be discussed later) are the most important interactions in structure (II) and are shown as large red spots on the HS.
The S atom of the phosphorothioic triamide molecule is not only involved in the two N—H···S hydrogen bonds (labels 4 and 6) with the two neighbouring cations, but it also takes part in an S···S contact with a neighbouring phosphorothioic triamide molecule (label 5). A search of the CSD shows that such an interaction was found only in one structure with a P(S)[N]3 segment, viz. [H2N][CH3NH]P(S)–N(CH3)–P(S)[NH2]2 (CSD refcode MTHPAM; Herbst-Irmer et al., 1996).
The other light-red spots in Fig. 6(a) (labels 7–15) are related to C—H···C interactions between the C—H units of the cation and the phosphorothioic triamide molecule, with the acceptor C atom belonging to the aromatic ring of the phosphorothioic triamide molecule. Furthermore, one NH unit of the cation participates in an N—H···Cl interaction that appears as a large red spot with label 16 in Fig. 6(b).
The Cl- anion in the crystal interacts with the above mentioned three NH units and with another one from the cation, resulting in four deep red spots in Fig. 6(c).
Two-dimensional fingerprint plots (FPs) are derived from the Hirshfeld surface (HS) by plotting the fraction of points on the surface as a function of (de, di), where de and di represent the distances from a point on the HS to the nearest atoms outside and inside the surface, respectively. The points are coloured as a function of the fraction of surface points, ranging from blue (relatively few points) through green (moderate fraction) to red (highest fraction) (McKinnon et al., 2004).
The FPs of the chemically equivalent molecules (IA) and (IB) (Figs. 7 and 8, and Fig. S1 in the Supporting information; in the following discussion, all figure numbers with a prefix `S' refer to figures that can be found in the Supporting information) are not identical because Hirshfeld surfaces and the corresponding FPs depend on the molecular conformation, as well as on the molecular environment in the crystal (Fabbiani et al., 2007). Molecule (IA), through two different N—H···S hydrogen bonds, is linked to molecules (IA) and (IB). For its part, molecule (IB) connects to molecule (IA) through the above-mentioned interaction and also connects to the acetonitrile solvent molecule via C—H···N and N—H···N interactions. As a result, the full FPs of molecules (IA) and (IB) are different (Figs. 7a and 8a).
Interactions of the types H···H, C···H/H···C, S···H/H···S and N···H/H···N exist for both molecules [Figs. 7b, 7c, S1a and S1b, respectively, for molecule (IA) , and Figs. 8b, 8c, S2a and S2b, respectively, for molecule (IB)]. Moreover, C···C interactions for both (IA) and (IB) and N···N and C···N interactions for (IB) have negligible contributions, which are not visible in FPs. The H···H contacts represent the largest relative contribution, amounting to 67.7% in (IA) and 64.3% in (IB), with one distinct spike for both molecules (Figs. 7b and 8b).
Furthermore, in the fingerprint plots of the two molecules, the C···H/H···C contacts [17.6% for (IA) (Fig. 7c) and 21% for (IB) (Fig. 8c)] appear as two short spikes, while the S···H/H···S interactions [10.3% in (IA) (Fig. S1a) and 7.6% for (IB) (Fig. S2a)] develop as two sharp spikes.
On the other hand, the contribution of N···H/H···N interactions in (IA) is very small (1.1%; Fig. S1b), whereas in (IB), it becomes more considerable (4.3%; Fig. S2b), with the differences between the spikes in the N···H diagram being very clear.
For structure (II), FPs are shown in Figs. 9(a), 9(b), 9(c), S3(a) and S3(b) for the phosphorothioic triamide molecule, in Figs. 10(a), 10(b), 10(c), S4(a) and S4(b) for the 3-methylpiperidinium cation, and in Fig. 11 for the chloride anion. The full FP for each component is not symmetric (Figs. 9a, 10a and 11), as the three components have quite different shapes and also each component has a different environment.
Figs. 9(b) and 9(c) depict the majority H···H (63.8%) and C···H/H···C (22.7%) contacts, while Fig. S3(a) shows the FP for the less important S···H/H···S (6.7%) contacts for the phosphorothioic triamide molecule. As for the C···H/H···C contacts (Fig. 9c), the shortest de + di (shown as blue points on the divided fingerprint) in spikes is near 2.6 Å and for S···H/H···S (Fig. S3a), it is near 2.3 Å. In contrast to the structure of (I), the N···H/H···N interactions have negligible contributions to the total interactions in (II).
For the [3-CH3—C5H9NH2]+ cation of (II), the full fingerprint plot is shown in Fig. 10(a). The most important interactions are the H···H contacts (62.9%; Fig. 10b), followed by H···C (22.5%; Fig. 10c), H···S (7.4%) and H···Cl (6.1%) (Figs. S4a and S4b, respectively). All the interactions discussed for the cation appear as a single spike in the region de > di in divided FPs, as expected. In other words, no S···H, Cl···H and meaningful C···H interactions were found with the cation, hence the corresponding fingerprint plots are quite asymmetric. Additionally, an acceptor spike is revealed for the Cl···H contacts which mostly concentrates in the region of de < di, the `lower part' of the fingerprint plot (Fig. 11). As there is no other interaction received by this anion, the interactions mentioned involve a 100% contribution to the Hirshfeld surface.
For both compounds, data collection: (CrysAlis PRO; Agilent, 2014); cell refinement: (CrysAlis PRO; Agilent, 2014); data reduction: (CrysAlis PRO; Agilent, 2014); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: JANA2006 (Petříček et al., 2014); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: enCIFer (Allen et al., 2004).
2C24H30N3PS·C2H3N | Z = 2 |
Mr = 888.2 | F(000) = 948 |
Triclinic, P1 | Dx = 1.218 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54184 Å |
a = 11.8547 (5) Å | Cell parameters from 6051 reflections |
b = 13.5312 (4) Å | θ = 3.3–67.0° |
c = 15.3394 (6) Å | µ = 1.94 mm−1 |
α = 91.849 (3)° | T = 120 K |
β = 98.378 (3)° | Polygon shape, white |
γ = 94.991 (3)° | 0.19 × 0.17 × 0.11 mm |
V = 2422.56 (16) Å3 |
Agilent Xcalibur (Atlas, Gemini ultra) diffractometer | 8394 independent reflections |
Radiation source: X-ray tube | 6369 reflections with I > 3σ(I) |
Mirror monochromator | Rint = 0.042 |
Detector resolution: 5.1873 pixels mm-1 | θmax = 67.1°, θmin = 3.3° |
ω scans | h = −13→14 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −16→13 |
Tmin = 0.658, Tmax = 1 | l = −18→13 |
15711 measured reflections |
Refinement on F | 234 constraints |
R[F2 > 2σ(F2)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.053 | Weighting scheme based on measured s.u.'s w = 1/(σ2(F) + 0.0001F2) |
S = 1.45 | (Δ/σ)max = 0.012 |
8394 reflections | Δρmax = 0.36 e Å−3 |
568 parameters | Δρmin = −0.26 e Å−3 |
6 restraints |
2C24H30N3PS·C2H3N | γ = 94.991 (3)° |
Mr = 888.2 | V = 2422.56 (16) Å3 |
Triclinic, P1 | Z = 2 |
a = 11.8547 (5) Å | Cu Kα radiation |
b = 13.5312 (4) Å | µ = 1.94 mm−1 |
c = 15.3394 (6) Å | T = 120 K |
α = 91.849 (3)° | 0.19 × 0.17 × 0.11 mm |
β = 98.378 (3)° |
Agilent Xcalibur (Atlas, Gemini ultra) diffractometer | 8394 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | 6369 reflections with I > 3σ(I) |
Tmin = 0.658, Tmax = 1 | Rint = 0.042 |
15711 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 6 restraints |
wR(F2) = 0.053 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.45 | Δρmax = 0.36 e Å−3 |
8394 reflections | Δρmin = −0.26 e Å−3 |
568 parameters |
Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Multi-scan absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement. The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program. |
x | y | z | Uiso*/Ueq | ||
S1a | 0.45406 (5) | 0.84796 (4) | 0.40382 (4) | 0.02819 (18) | |
P1a | 0.53714 (5) | 0.97192 (4) | 0.37541 (4) | 0.02405 (18) | |
S1b | 0.42803 (5) | 0.77086 (4) | 0.13783 (4) | 0.03331 (19) | |
P1b | 0.44642 (5) | 0.63722 (4) | 0.17822 (4) | 0.02589 (18) | |
N2a | 0.57137 (17) | 0.95709 (13) | 0.27667 (13) | 0.0275 (6) | |
N3b | 0.49367 (17) | 0.64552 (13) | 0.28479 (13) | 0.0287 (6) | |
N1b | 0.32971 (17) | 0.55794 (14) | 0.16015 (13) | 0.0306 (6) | |
C12a | 0.7301 (2) | 1.16239 (18) | 0.11946 (16) | 0.0331 (8) | |
C11a | 0.6892 (2) | 1.06682 (18) | 0.08830 (18) | 0.0395 (9) | |
C19a | 0.8508 (2) | 0.81035 (17) | 0.46913 (17) | 0.0332 (8) | |
C5b | 0.0520 (2) | 0.4793 (2) | 0.22765 (19) | 0.0426 (9) | |
N1a | 0.46811 (17) | 1.07283 (13) | 0.37898 (13) | 0.0282 (6) | |
C7b | 0.0875 (2) | 0.73721 (19) | 0.33593 (19) | 0.0447 (10) | |
C10b | 0.6953 (2) | 0.52333 (19) | 0.06945 (17) | 0.0356 (8) | |
N2b | 0.52934 (17) | 0.57056 (14) | 0.12711 (14) | 0.0326 (7) | |
C7a | 0.1551 (3) | 0.9734 (2) | 0.1337 (2) | 0.0524 (11) | |
C4b | 0.0283 (2) | 0.56120 (19) | 0.27607 (18) | 0.0389 (9) | |
C9a | 0.6256 (2) | 1.02799 (16) | 0.22549 (15) | 0.0274 (7) | |
C20b | 0.6401 (2) | 0.42819 (17) | 0.44595 (17) | 0.0335 (8) | |
C3b | 0.1072 (2) | 0.64451 (18) | 0.28598 (16) | 0.0333 (8) | |
N3a | 0.65448 (16) | 1.01093 (13) | 0.44398 (13) | 0.0261 (6) | |
C24b | 0.6973 (3) | 0.35174 (19) | 0.5011 (2) | 0.0453 (10) | |
C10a | 0.6383 (2) | 1.00005 (18) | 0.14031 (17) | 0.0379 (9) | |
C21b | 0.6625 (2) | 0.52997 (17) | 0.47083 (16) | 0.0297 (8) | |
C18b | 0.5133 (2) | 0.46978 (16) | 0.31617 (17) | 0.0339 (8) | |
C19b | 0.5650 (2) | 0.40171 (17) | 0.36961 (17) | 0.0367 (9) | |
C24a | 1.0261 (2) | 0.7873 (2) | 0.5773 (2) | 0.0465 (10) | |
C20a | 0.9300 (2) | 0.84639 (17) | 0.54029 (17) | 0.0337 (8) | |
C6b | 0.1508 (2) | 0.47772 (18) | 0.18969 (17) | 0.0364 (8) | |
N4 | 0.4354 (3) | 0.35711 (18) | 0.10487 (19) | 0.0730 (13) | |
C16a | 0.7595 (2) | 1.29352 (18) | 0.24193 (18) | 0.0434 (10) | |
C3a | 0.2147 (2) | 1.04925 (19) | 0.20156 (17) | 0.0383 (9) | |
C11b | 0.8041 (2) | 0.5449 (2) | 0.05012 (17) | 0.0399 (9) | |
C17b | 0.53862 (19) | 0.57039 (16) | 0.33906 (15) | 0.0268 (7) | |
C15a | 0.7838 (2) | 1.23445 (19) | 0.06074 (18) | 0.0413 (9) | |
C4a | 0.1772 (2) | 1.14392 (18) | 0.21103 (17) | 0.0369 (9) | |
C5a | 0.2335 (2) | 1.21025 (19) | 0.27517 (18) | 0.0413 (9) | |
C14b | 0.7017 (2) | 0.68695 (18) | 0.13451 (17) | 0.0346 (8) | |
C23b | 0.7417 (2) | 0.56380 (19) | 0.55388 (18) | 0.0426 (9) | |
C18a | 0.7593 (2) | 0.86216 (16) | 0.43452 (16) | 0.0297 (8) | |
C22b | 0.6113 (2) | 0.59902 (16) | 0.41631 (15) | 0.0281 (7) | |
C14a | 0.6661 (2) | 1.12338 (16) | 0.25769 (16) | 0.0300 (8) | |
C9b | 0.6421 (2) | 0.59541 (17) | 0.11145 (16) | 0.0298 (8) | |
C1b | 0.2301 (2) | 0.56106 (16) | 0.19988 (15) | 0.0277 (7) | |
C13b | 0.8117 (2) | 0.70960 (19) | 0.11377 (18) | 0.0391 (9) | |
C15b | 0.9830 (2) | 0.6584 (2) | 0.0468 (2) | 0.0530 (11) | |
C22a | 0.82669 (19) | 0.99142 (16) | 0.54501 (15) | 0.0278 (7) | |
C13a | 0.7179 (2) | 1.19063 (16) | 0.20548 (16) | 0.0305 (8) | |
C16b | 0.8718 (3) | 0.8107 (2) | 0.1375 (2) | 0.0542 (11) | |
C17a | 0.74582 (19) | 0.95328 (15) | 0.47407 (15) | 0.0255 (7) | |
C21a | 0.9184 (2) | 0.94052 (17) | 0.57864 (16) | 0.0307 (8) | |
C8b | −0.0809 (3) | 0.5601 (2) | 0.3163 (2) | 0.0558 (12) | |
C2a | 0.3116 (2) | 1.02488 (18) | 0.25837 (17) | 0.0350 (8) | |
C2b | 0.2073 (2) | 0.64355 (17) | 0.24787 (16) | 0.0307 (8) | |
C12b | 0.8637 (2) | 0.6375 (2) | 0.07018 (17) | 0.0387 (9) | |
C25 | 0.4266 (2) | 0.2741 (2) | 0.09140 (18) | 0.0421 (10) | |
C6a | 0.3295 (2) | 1.18666 (17) | 0.33053 (18) | 0.0365 (9) | |
C23a | 1.0045 (2) | 0.98559 (19) | 0.65409 (18) | 0.0401 (9) | |
C1a | 0.3692 (2) | 1.09322 (17) | 0.32166 (16) | 0.0306 (8) | |
C8a | 0.0732 (3) | 1.1710 (2) | 0.1498 (2) | 0.0602 (12) | |
C26 | 0.4114 (3) | 0.16901 (19) | 0.0710 (2) | 0.0502 (11) | |
H1c11a | 0.696461 | 1.046443 | 0.028998 | 0.0474* | |
H1c19a | 0.859067 | 0.746832 | 0.442278 | 0.0398* | |
H1c5b | −0.002172 | 0.421498 | 0.220186 | 0.0511* | |
H1c7b | 0.147081 | 0.788376 | 0.330482 | 0.0536* | |
H2c7b | 0.01468 | 0.758793 | 0.3122 | 0.0536* | |
H3c7b | 0.088043 | 0.723696 | 0.397044 | 0.0536* | |
H1c10b | 0.655834 | 0.458729 | 0.054084 | 0.0427* | |
H1c7a | 0.189528 | 0.911984 | 0.141471 | 0.0629* | |
H2c7a | 0.075679 | 0.963185 | 0.140157 | 0.0629* | |
H3c7a | 0.161939 | 0.996159 | 0.07594 | 0.0629* | |
H1c24b | 0.67448 | 0.353885 | 0.558594 | 0.0544* | |
H2c24b | 0.675181 | 0.286959 | 0.473361 | 0.0544* | |
H3c24b | 0.778947 | 0.365521 | 0.506566 | 0.0544* | |
H1c10a | 0.611688 | 0.934019 | 0.11718 | 0.0455* | |
H1c18b | 0.460639 | 0.448161 | 0.264061 | 0.0406* | |
H1c19b | 0.548096 | 0.332419 | 0.352921 | 0.0441* | |
H1c24a | 1.022043 | 0.776514 | 0.638399 | 0.0558* | |
H2c24a | 1.019426 | 0.724425 | 0.545251 | 0.0558* | |
H3c24a | 1.098083 | 0.823115 | 0.572002 | 0.0558* | |
H1c6b | 0.164635 | 0.419707 | 0.156605 | 0.0436* | |
H1c16a | 0.754468 | 1.297776 | 0.303817 | 0.052* | |
H2c16a | 0.837632 | 1.30844 | 0.233335 | 0.052* | |
H3c16a | 0.712922 | 1.340294 | 0.211977 | 0.052* | |
H1c11b | 0.839984 | 0.494345 | 0.021883 | 0.0479* | |
H1c15a | 0.78957 | 1.201001 | 0.005625 | 0.0496* | |
H2c15a | 0.737185 | 1.288621 | 0.050167 | 0.0496* | |
H3c15a | 0.858914 | 1.259507 | 0.089127 | 0.0496* | |
H1c5a | 0.205978 | 1.274306 | 0.281973 | 0.0496* | |
H1c14b | 0.666917 | 0.736078 | 0.165432 | 0.0415* | |
H1c23b | 0.816166 | 0.542239 | 0.550849 | 0.0512* | |
H2c23b | 0.74749 | 0.634952 | 0.560232 | 0.0512* | |
H3c23b | 0.712259 | 0.535848 | 0.603653 | 0.0512* | |
H1c18a | 0.706421 | 0.835353 | 0.384194 | 0.0356* | |
H1c22b | 0.626963 | 0.66843 | 0.432855 | 0.0338* | |
H1c14a | 0.65836 | 1.143399 | 0.316972 | 0.0359* | |
H1c15b | 0.994436 | 0.726595 | 0.031976 | 0.0636* | |
H2c15b | 1.03851 | 0.64592 | 0.09633 | 0.0636* | |
H3c15b | 0.991537 | 0.616022 | −0.002738 | 0.0636* | |
H1c22a | 0.818431 | 1.055175 | 0.571423 | 0.0333* | |
H1c16b | 0.833729 | 0.843968 | 0.17947 | 0.0651* | |
H2c16b | 0.949725 | 0.804684 | 0.16296 | 0.0651* | |
H3c16b | 0.870607 | 0.848329 | 0.085487 | 0.0651* | |
H1c8b | −0.062509 | 0.575497 | 0.378561 | 0.067* | |
H2c8b | −0.12751 | 0.608765 | 0.289461 | 0.067* | |
H3c8b | −0.122096 | 0.495519 | 0.306387 | 0.067* | |
H1c2a | 0.337785 | 0.960111 | 0.253035 | 0.042* | |
H1c2b | 0.261379 | 0.70133 | 0.255125 | 0.0369* | |
H1c6a | 0.368589 | 1.234374 | 0.374855 | 0.0438* | |
H1c23a | 1.012817 | 0.939591 | 0.700448 | 0.0481* | |
H2c23a | 1.077014 | 1.00028 | 0.634175 | 0.0481* | |
H3c23a | 0.978839 | 1.045712 | 0.675874 | 0.0481* | |
H1c8a | 0.022086 | 1.112395 | 0.132753 | 0.0722* | |
H2c8a | 0.034629 | 1.218306 | 0.179601 | 0.0722* | |
H3c8a | 0.097169 | 1.199469 | 0.098157 | 0.0722* | |
H1c26 | 0.424592 | 0.134141 | 0.124548 | 0.0602* | |
H2c26 | 0.33465 | 0.150877 | 0.042029 | 0.0602* | |
H3c26 | 0.464723 | 0.151755 | 0.032871 | 0.0602* | |
H1n3b | 0.493 (2) | 0.7023 (11) | 0.3123 (15) | 0.0345* | |
H1n1b | 0.328 (2) | 0.5095 (14) | 0.1221 (14) | 0.0367* | |
H1n3a | 0.648 (2) | 1.0565 (14) | 0.4833 (13) | 0.0313* | |
H1n2a | 0.544 (2) | 0.9012 (11) | 0.2494 (15) | 0.033* | |
H1n2b | 0.506 (2) | 0.5086 (9) | 0.1151 (18) | 0.0391* | |
H1n1a | 0.481 (2) | 1.1070 (16) | 0.4289 (10) | 0.0339* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1a | 0.0323 (3) | 0.0238 (3) | 0.0294 (3) | −0.0003 (2) | 0.0100 (2) | −0.0012 (2) |
P1a | 0.0248 (3) | 0.0229 (3) | 0.0253 (3) | 0.0017 (2) | 0.0070 (2) | 0.0007 (2) |
S1b | 0.0380 (3) | 0.0305 (3) | 0.0302 (3) | 0.0039 (2) | 0.0006 (3) | 0.0008 (2) |
P1b | 0.0239 (3) | 0.0278 (3) | 0.0258 (3) | 0.0021 (2) | 0.0040 (2) | −0.0025 (2) |
N2a | 0.0334 (11) | 0.0233 (9) | 0.0261 (11) | −0.0021 (8) | 0.0090 (8) | −0.0021 (8) |
N3b | 0.0319 (11) | 0.0247 (9) | 0.0286 (11) | 0.0039 (8) | 0.0016 (9) | −0.0032 (8) |
N1b | 0.0274 (11) | 0.0317 (10) | 0.0312 (11) | −0.0011 (8) | 0.0050 (9) | −0.0115 (8) |
C12a | 0.0291 (13) | 0.0393 (13) | 0.0332 (14) | 0.0059 (10) | 0.0090 (11) | 0.0092 (11) |
C11a | 0.0497 (17) | 0.0386 (14) | 0.0341 (15) | 0.0028 (12) | 0.0199 (12) | 0.0016 (11) |
C19a | 0.0343 (14) | 0.0304 (12) | 0.0386 (15) | 0.0068 (10) | 0.0159 (11) | 0.0001 (11) |
C5b | 0.0377 (15) | 0.0441 (15) | 0.0456 (17) | −0.0088 (12) | 0.0132 (13) | −0.0033 (12) |
N1a | 0.0300 (11) | 0.0270 (10) | 0.0291 (11) | 0.0061 (8) | 0.0074 (9) | −0.0007 (8) |
C7b | 0.0417 (16) | 0.0490 (15) | 0.0463 (17) | 0.0149 (13) | 0.0113 (13) | −0.0032 (13) |
C10b | 0.0344 (14) | 0.0397 (13) | 0.0341 (14) | 0.0084 (11) | 0.0074 (11) | 0.0008 (11) |
N2b | 0.0315 (11) | 0.0299 (10) | 0.0372 (12) | 0.0000 (9) | 0.0116 (9) | −0.0069 (9) |
C7a | 0.0486 (18) | 0.0539 (17) | 0.0524 (19) | 0.0025 (14) | 0.0028 (14) | −0.0071 (15) |
C4b | 0.0329 (14) | 0.0475 (15) | 0.0371 (15) | 0.0019 (12) | 0.0089 (12) | 0.0013 (12) |
C9a | 0.0262 (12) | 0.0293 (11) | 0.0285 (13) | 0.0041 (9) | 0.0089 (10) | 0.0047 (10) |
C20b | 0.0348 (14) | 0.0318 (12) | 0.0363 (14) | 0.0042 (10) | 0.0116 (11) | 0.0067 (11) |
C3b | 0.0309 (13) | 0.0408 (13) | 0.0282 (13) | 0.0070 (11) | 0.0025 (10) | −0.0016 (11) |
N3a | 0.0278 (10) | 0.0235 (9) | 0.0272 (11) | 0.0027 (8) | 0.0059 (8) | −0.0031 (8) |
C24b | 0.0536 (18) | 0.0359 (14) | 0.0474 (17) | 0.0057 (12) | 0.0075 (14) | 0.0125 (12) |
C10a | 0.0480 (16) | 0.0300 (12) | 0.0385 (15) | 0.0009 (11) | 0.0173 (12) | −0.0003 (11) |
C21b | 0.0284 (13) | 0.0342 (12) | 0.0282 (13) | 0.0039 (10) | 0.0085 (10) | 0.0033 (10) |
C18b | 0.0383 (14) | 0.0284 (12) | 0.0327 (14) | −0.0010 (10) | 0.0012 (11) | −0.0016 (10) |
C19b | 0.0421 (15) | 0.0258 (12) | 0.0420 (15) | 0.0001 (10) | 0.0077 (12) | −0.0002 (11) |
C24a | 0.0405 (16) | 0.0543 (16) | 0.0476 (17) | 0.0178 (13) | 0.0075 (13) | 0.0056 (14) |
C20a | 0.0296 (13) | 0.0377 (13) | 0.0370 (14) | 0.0064 (10) | 0.0126 (11) | 0.0066 (11) |
C6b | 0.0360 (14) | 0.0357 (13) | 0.0362 (15) | −0.0034 (11) | 0.0072 (11) | −0.0064 (11) |
N4 | 0.131 (3) | 0.0330 (14) | 0.0522 (17) | −0.0003 (15) | 0.0126 (17) | −0.0056 (12) |
C16a | 0.0485 (17) | 0.0375 (14) | 0.0435 (17) | −0.0047 (12) | 0.0101 (14) | 0.0023 (12) |
C3a | 0.0382 (15) | 0.0439 (14) | 0.0330 (14) | −0.0038 (11) | 0.0109 (12) | 0.0008 (11) |
C11b | 0.0351 (15) | 0.0523 (16) | 0.0356 (15) | 0.0160 (12) | 0.0088 (12) | 0.0055 (12) |
C17b | 0.0267 (12) | 0.0270 (11) | 0.0272 (12) | 0.0016 (9) | 0.0059 (10) | 0.0016 (9) |
C15a | 0.0399 (16) | 0.0451 (15) | 0.0407 (16) | −0.0001 (12) | 0.0121 (12) | 0.0106 (12) |
C4a | 0.0368 (15) | 0.0378 (13) | 0.0383 (15) | 0.0044 (11) | 0.0106 (12) | 0.0090 (11) |
C5a | 0.0418 (16) | 0.0370 (14) | 0.0463 (17) | 0.0071 (12) | 0.0075 (13) | 0.0049 (12) |
C14b | 0.0289 (13) | 0.0382 (13) | 0.0364 (14) | 0.0046 (10) | 0.0041 (11) | −0.0003 (11) |
C23b | 0.0495 (17) | 0.0418 (14) | 0.0348 (15) | 0.0065 (12) | −0.0017 (13) | 0.0039 (12) |
C18a | 0.0294 (13) | 0.0287 (12) | 0.0316 (13) | 0.0010 (10) | 0.0091 (10) | −0.0036 (10) |
C22b | 0.0301 (13) | 0.0261 (11) | 0.0283 (13) | 0.0024 (9) | 0.0053 (10) | −0.0011 (10) |
C14a | 0.0295 (13) | 0.0319 (12) | 0.0288 (13) | −0.0004 (10) | 0.0076 (10) | 0.0018 (10) |
C9b | 0.0273 (13) | 0.0371 (13) | 0.0264 (13) | 0.0063 (10) | 0.0066 (10) | 0.0042 (10) |
C1b | 0.0253 (12) | 0.0333 (12) | 0.0239 (12) | 0.0030 (9) | 0.0015 (10) | 0.0001 (10) |
C13b | 0.0299 (14) | 0.0463 (14) | 0.0401 (15) | 0.0014 (11) | 0.0009 (11) | 0.0107 (12) |
C15b | 0.0322 (15) | 0.078 (2) | 0.0536 (19) | 0.0126 (14) | 0.0118 (13) | 0.0228 (17) |
C22a | 0.0283 (12) | 0.0280 (11) | 0.0281 (13) | −0.0003 (9) | 0.0099 (10) | −0.0010 (10) |
C13a | 0.0248 (12) | 0.0304 (12) | 0.0358 (14) | 0.0021 (9) | 0.0018 (10) | 0.0051 (10) |
C16b | 0.0366 (17) | 0.0560 (17) | 0.068 (2) | −0.0067 (14) | 0.0050 (15) | 0.0063 (15) |
C17a | 0.0244 (12) | 0.0251 (11) | 0.0286 (12) | 0.0007 (9) | 0.0099 (10) | 0.0039 (9) |
C21a | 0.0270 (13) | 0.0378 (13) | 0.0286 (13) | −0.0010 (10) | 0.0106 (10) | 0.0036 (10) |
C8b | 0.0449 (18) | 0.0626 (19) | 0.064 (2) | −0.0009 (14) | 0.0263 (16) | −0.0024 (16) |
C2a | 0.0330 (14) | 0.0388 (13) | 0.0357 (14) | 0.0039 (11) | 0.0121 (11) | 0.0077 (11) |
C2b | 0.0277 (13) | 0.0326 (12) | 0.0306 (13) | 0.0025 (10) | 0.0015 (10) | −0.0034 (10) |
C12b | 0.0271 (13) | 0.0587 (16) | 0.0323 (14) | 0.0089 (12) | 0.0055 (11) | 0.0156 (12) |
C25 | 0.0541 (18) | 0.0388 (15) | 0.0326 (15) | −0.0001 (12) | 0.0081 (13) | −0.0038 (12) |
C6a | 0.0374 (15) | 0.0315 (12) | 0.0415 (15) | 0.0043 (11) | 0.0075 (12) | 0.0058 (11) |
C23a | 0.0318 (14) | 0.0502 (15) | 0.0373 (15) | 0.0016 (12) | 0.0033 (12) | 0.0046 (12) |
C1a | 0.0279 (13) | 0.0370 (13) | 0.0288 (13) | 0.0020 (10) | 0.0097 (10) | 0.0073 (10) |
C8a | 0.055 (2) | 0.066 (2) | 0.059 (2) | 0.0148 (16) | −0.0014 (16) | 0.0086 (16) |
C26 | 0.059 (2) | 0.0400 (15) | 0.0527 (19) | 0.0002 (13) | 0.0159 (15) | −0.0003 (13) |
S1a—P1a | 1.9643 (8) | C20a—C21a | 1.412 (3) |
P1a—N2a | 1.635 (2) | C6b—C1b | 1.393 (3) |
P1a—N1a | 1.655 (2) | C6b—H1c6b | 0.96 |
P1a—N3a | 1.6523 (18) | N4—C25 | 1.128 (4) |
S1b—P1b | 1.9501 (8) | C16a—C13a | 1.498 (3) |
P1b—N3b | 1.646 (2) | C16a—H1c16a | 0.96 |
P1b—N1b | 1.6591 (19) | C16a—H2c16a | 0.96 |
P1b—N2b | 1.652 (2) | C16a—H3c16a | 0.96 |
N2a—C9a | 1.427 (3) | C3a—C4a | 1.402 (4) |
N2a—H1n2a | 0.866 (17) | C3a—C2a | 1.407 (4) |
N3b—C17b | 1.425 (3) | C11b—C12b | 1.386 (4) |
N3b—H1n3b | 0.865 (17) | C11b—H1c11b | 0.96 |
N1b—C1b | 1.409 (3) | C17b—C22b | 1.383 (3) |
N1b—H1n1b | 0.86 (2) | C15a—H1c15a | 0.96 |
C12a—C11a | 1.385 (3) | C15a—H2c15a | 0.96 |
C12a—C15a | 1.511 (4) | C15a—H3c15a | 0.96 |
C12a—C13a | 1.393 (4) | C4a—C5a | 1.366 (3) |
C11a—C10a | 1.382 (4) | C4a—C8a | 1.517 (4) |
C11a—H1c11a | 0.96 | C5a—C6a | 1.385 (4) |
C19a—C20a | 1.378 (3) | C5a—H1c5a | 0.96 |
C19a—C18a | 1.393 (3) | C14b—C9b | 1.380 (3) |
C19a—H1c19a | 0.96 | C14b—C13b | 1.398 (4) |
C5b—C4b | 1.386 (4) | C14b—H1c14b | 0.96 |
C5b—C6b | 1.384 (4) | C23b—H1c23b | 0.96 |
C5b—H1c5b | 0.96 | C23b—H2c23b | 0.96 |
N1a—C1a | 1.412 (3) | C23b—H3c23b | 0.96 |
N1a—H1n1a | 0.869 (17) | C18a—C17a | 1.388 (3) |
C7b—C3b | 1.502 (4) | C18a—H1c18a | 0.96 |
C7b—H1c7b | 0.96 | C22b—H1c22b | 0.96 |
C7b—H2c7b | 0.96 | C14a—C13a | 1.393 (3) |
C7b—H3c7b | 0.96 | C14a—H1c14a | 0.96 |
C10b—C11b | 1.375 (4) | C1b—C2b | 1.385 (3) |
C10b—C9b | 1.396 (4) | C13b—C16b | 1.495 (4) |
C10b—H1c10b | 0.96 | C13b—C12b | 1.400 (4) |
N2b—C9b | 1.406 (3) | C15b—C12b | 1.514 (4) |
N2b—H1n2b | 0.864 (13) | C15b—H1c15b | 0.96 |
C7a—C3a | 1.492 (4) | C15b—H2c15b | 0.96 |
C7a—H1c7a | 0.96 | C15b—H3c15b | 0.96 |
C7a—H2c7a | 0.96 | C22a—C17a | 1.394 (3) |
C7a—H3c7a | 0.96 | C22a—C21a | 1.383 (3) |
C4b—C3b | 1.390 (3) | C22a—H1c22a | 0.96 |
C4b—C8b | 1.513 (4) | C16b—H1c16b | 0.96 |
C9a—C10a | 1.381 (4) | C16b—H2c16b | 0.96 |
C9a—C14a | 1.387 (3) | C16b—H3c16b | 0.96 |
C20b—C24b | 1.503 (4) | C21a—C23a | 1.502 (3) |
C20b—C21b | 1.409 (3) | C8b—H1c8b | 0.96 |
C20b—C19b | 1.380 (3) | C8b—H2c8b | 0.96 |
C3b—C2b | 1.398 (4) | C8b—H3c8b | 0.96 |
N3a—C17a | 1.421 (3) | C2a—C1a | 1.380 (3) |
N3a—H1n3a | 0.86 (2) | C2a—H1c2a | 0.96 |
C24b—H1c24b | 0.96 | C2b—H1c2b | 0.96 |
C24b—H2c24b | 0.96 | C25—C26 | 1.436 (4) |
C24b—H3c24b | 0.96 | C6a—C1a | 1.397 (3) |
C10a—H1c10a | 0.96 | C6a—H1c6a | 0.96 |
C21b—C23b | 1.501 (3) | C23a—H1c23a | 0.96 |
C21b—C22b | 1.393 (3) | C23a—H2c23a | 0.96 |
C18b—C19b | 1.378 (3) | C23a—H3c23a | 0.96 |
C18b—C17b | 1.391 (3) | C8a—H1c8a | 0.96 |
C18b—H1c18b | 0.96 | C8a—H2c8a | 0.96 |
C19b—H1c19b | 0.96 | C8a—H3c8a | 0.96 |
C24a—C20a | 1.503 (4) | C26—H1c26 | 0.96 |
C24a—H1c24a | 0.96 | C26—H2c26 | 0.96 |
C24a—H2c24a | 0.96 | C26—H3c26 | 0.96 |
C24a—H3c24a | 0.96 | ||
S1a—P1a—N2a | 108.21 (7) | C10b—C11b—H1c11b | 119.02 |
S1a—P1a—N1a | 115.88 (8) | C12b—C11b—H1c11b | 119.02 |
S1a—P1a—N3a | 116.27 (7) | N3b—C17b—C18b | 122.24 (19) |
N2a—P1a—N1a | 108.72 (10) | N3b—C17b—C22b | 118.57 (19) |
N2a—P1a—N3a | 108.38 (10) | C18b—C17b—C22b | 119.2 (2) |
N1a—P1a—N3a | 98.85 (9) | C12a—C15a—H1c15a | 109.47 |
S1b—P1b—N3b | 108.31 (7) | C12a—C15a—H2c15a | 109.47 |
S1b—P1b—N1b | 115.80 (8) | C12a—C15a—H3c15a | 109.47 |
S1b—P1b—N2b | 116.55 (8) | H1c15a—C15a—H2c15a | 109.47 |
N3b—P1b—N1b | 108.65 (10) | H1c15a—C15a—H3c15a | 109.47 |
N3b—P1b—N2b | 109.73 (10) | H2c15a—C15a—H3c15a | 109.47 |
N1b—P1b—N2b | 97.25 (10) | C3a—C4a—C5a | 120.1 (2) |
P1a—N2a—C9a | 128.87 (15) | C3a—C4a—C8a | 119.1 (2) |
P1a—N2a—H1n2a | 114.5 (16) | C5a—C4a—C8a | 120.7 (2) |
C9a—N2a—H1n2a | 116.0 (16) | C4a—C5a—C6a | 121.1 (2) |
P1b—N3b—C17b | 128.04 (15) | C4a—C5a—H1c5a | 119.44 |
P1b—N3b—H1n3b | 117.7 (15) | C6a—C5a—H1c5a | 119.44 |
C17b—N3b—H1n3b | 114.3 (15) | C9b—C14b—C13b | 121.4 (2) |
P1b—N1b—C1b | 127.14 (16) | C9b—C14b—H1c14b | 119.32 |
P1b—N1b—H1n1b | 117.6 (17) | C13b—C14b—H1c14b | 119.32 |
C1b—N1b—H1n1b | 115.3 (17) | C21b—C23b—H1c23b | 109.47 |
C11a—C12a—C15a | 120.7 (2) | C21b—C23b—H2c23b | 109.47 |
C11a—C12a—C13a | 118.2 (2) | C21b—C23b—H3c23b | 109.47 |
C15a—C12a—C13a | 121.1 (2) | H1c23b—C23b—H2c23b | 109.47 |
C12a—C11a—C10a | 121.7 (2) | H1c23b—C23b—H3c23b | 109.47 |
C12a—C11a—H1c11a | 119.13 | H2c23b—C23b—H3c23b | 109.47 |
C10a—C11a—H1c11a | 119.13 | C19a—C18a—C17a | 118.8 (2) |
C20a—C19a—C18a | 122.8 (2) | C19a—C18a—H1c18a | 120.58 |
C20a—C19a—H1c19a | 118.61 | C17a—C18a—H1c18a | 120.58 |
C18a—C19a—H1c19a | 118.61 | C21b—C22b—C17b | 121.9 (2) |
C4b—C5b—C6b | 122.4 (2) | C21b—C22b—H1c22b | 119.07 |
C4b—C5b—H1c5b | 118.82 | C17b—C22b—H1c22b | 119.07 |
C6b—C5b—H1c5b | 118.82 | C9a—C14a—C13a | 121.1 (2) |
P1a—N1a—C1a | 126.46 (15) | C9a—C14a—H1c14a | 119.44 |
P1a—N1a—H1n1a | 115.7 (15) | C13a—C14a—H1c14a | 119.44 |
C1a—N1a—H1n1a | 115.0 (17) | C10b—C9b—N2b | 117.7 (2) |
C3b—C7b—H1c7b | 109.47 | C10b—C9b—C14b | 118.8 (2) |
C3b—C7b—H2c7b | 109.47 | N2b—C9b—C14b | 123.6 (2) |
C3b—C7b—H3c7b | 109.47 | N1b—C1b—C6b | 118.4 (2) |
H1c7b—C7b—H2c7b | 109.47 | N1b—C1b—C2b | 122.9 (2) |
H1c7b—C7b—H3c7b | 109.47 | C6b—C1b—C2b | 118.7 (2) |
H2c7b—C7b—H3c7b | 109.47 | C14b—C13b—C16b | 119.6 (2) |
C11b—C10b—C9b | 119.9 (2) | C14b—C13b—C12b | 119.5 (2) |
C11b—C10b—H1c10b | 120.03 | C16b—C13b—C12b | 120.9 (2) |
C9b—C10b—H1c10b | 120.03 | C12b—C15b—H1c15b | 109.47 |
P1b—N2b—C9b | 129.06 (16) | C12b—C15b—H2c15b | 109.47 |
P1b—N2b—H1n2b | 117.0 (19) | C12b—C15b—H3c15b | 109.47 |
C9b—N2b—H1n2b | 113.2 (19) | H1c15b—C15b—H2c15b | 109.47 |
C3a—C7a—H1c7a | 109.47 | H1c15b—C15b—H3c15b | 109.47 |
C3a—C7a—H2c7a | 109.47 | H2c15b—C15b—H3c15b | 109.47 |
C3a—C7a—H3c7a | 109.47 | C17a—C22a—C21a | 122.2 (2) |
H1c7a—C7a—H2c7a | 109.47 | C17a—C22a—H1c22a | 118.89 |
H1c7a—C7a—H3c7a | 109.47 | C21a—C22a—H1c22a | 118.89 |
H2c7a—C7a—H3c7a | 109.47 | C12a—C13a—C16a | 120.2 (2) |
C5b—C4b—C3b | 118.2 (3) | C12a—C13a—C14a | 120.0 (2) |
C5b—C4b—C8b | 120.8 (2) | C16a—C13a—C14a | 119.8 (2) |
C3b—C4b—C8b | 121.0 (2) | C13b—C16b—H1c16b | 109.47 |
N2a—C9a—C10a | 118.44 (19) | C13b—C16b—H2c16b | 109.47 |
N2a—C9a—C14a | 122.8 (2) | C13b—C16b—H3c16b | 109.47 |
C10a—C9a—C14a | 118.7 (2) | H1c16b—C16b—H2c16b | 109.47 |
C24b—C20b—C21b | 120.5 (2) | H1c16b—C16b—H3c16b | 109.47 |
C24b—C20b—C19b | 121.6 (2) | H2c16b—C16b—H3c16b | 109.47 |
C21b—C20b—C19b | 117.9 (2) | N3a—C17a—C18a | 122.83 (19) |
C7b—C3b—C4b | 121.8 (2) | N3a—C17a—C22a | 118.26 (19) |
C7b—C3b—C2b | 118.4 (2) | C18a—C17a—C22a | 118.9 (2) |
C4b—C3b—C2b | 119.8 (2) | C20a—C21a—C22a | 118.9 (2) |
P1a—N3a—C17a | 126.12 (14) | C20a—C21a—C23a | 120.9 (2) |
P1a—N3a—H1n3a | 116.6 (16) | C22a—C21a—C23a | 120.2 (2) |
C17a—N3a—H1n3a | 110.6 (15) | C4b—C8b—H1c8b | 109.47 |
C20b—C24b—H1c24b | 109.47 | C4b—C8b—H2c8b | 109.47 |
C20b—C24b—H2c24b | 109.47 | C4b—C8b—H3c8b | 109.47 |
C20b—C24b—H3c24b | 109.47 | H1c8b—C8b—H2c8b | 109.47 |
H1c24b—C24b—H2c24b | 109.47 | H1c8b—C8b—H3c8b | 109.47 |
H1c24b—C24b—H3c24b | 109.47 | H2c8b—C8b—H3c8b | 109.47 |
H2c24b—C24b—H3c24b | 109.47 | C3a—C2a—C1a | 120.6 (2) |
C11a—C10a—C9a | 120.2 (2) | C3a—C2a—H1c2a | 119.7 |
C11a—C10a—H1c10a | 119.89 | C1a—C2a—H1c2a | 119.7 |
C9a—C10a—H1c10a | 119.89 | C3b—C2b—C1b | 121.5 (2) |
C20b—C21b—C23b | 120.7 (2) | C3b—C2b—H1c2b | 119.28 |
C20b—C21b—C22b | 118.9 (2) | C1b—C2b—H1c2b | 119.27 |
C23b—C21b—C22b | 120.4 (2) | C11b—C12b—C13b | 118.4 (2) |
C19b—C18b—C17b | 118.8 (2) | C11b—C12b—C15b | 120.2 (3) |
C19b—C18b—H1c18b | 120.59 | C13b—C12b—C15b | 121.4 (2) |
C17b—C18b—H1c18b | 120.59 | N4—C25—C26 | 177.4 (3) |
C20b—C19b—C18b | 123.2 (2) | C5a—C6a—C1a | 119.8 (2) |
C20b—C19b—H1c19b | 118.38 | C5a—C6a—H1c6a | 120.12 |
C18b—C19b—H1c19b | 118.38 | C1a—C6a—H1c6a | 120.12 |
C20a—C24a—H1c24a | 109.47 | C21a—C23a—H1c23a | 109.47 |
C20a—C24a—H2c24a | 109.47 | C21a—C23a—H2c23a | 109.47 |
C20a—C24a—H3c24a | 109.47 | C21a—C23a—H3c23a | 109.47 |
H1c24a—C24a—H2c24a | 109.47 | H1c23a—C23a—H2c23a | 109.47 |
H1c24a—C24a—H3c24a | 109.47 | H1c23a—C23a—H3c23a | 109.47 |
H2c24a—C24a—H3c24a | 109.47 | H2c23a—C23a—H3c23a | 109.47 |
C19a—C20a—C24a | 121.3 (2) | N1a—C1a—C2a | 122.6 (2) |
C19a—C20a—C21a | 118.3 (2) | N1a—C1a—C6a | 117.8 (2) |
C24a—C20a—C21a | 120.3 (2) | C2a—C1a—C6a | 119.6 (2) |
C5b—C6b—C1b | 119.4 (2) | C4a—C8a—H1c8a | 109.47 |
C5b—C6b—H1c6b | 120.28 | C4a—C8a—H2c8a | 109.47 |
C1b—C6b—H1c6b | 120.28 | C4a—C8a—H3c8a | 109.47 |
C13a—C16a—H1c16a | 109.47 | H1c8a—C8a—H2c8a | 109.47 |
C13a—C16a—H2c16a | 109.47 | H1c8a—C8a—H3c8a | 109.47 |
C13a—C16a—H3c16a | 109.47 | H2c8a—C8a—H3c8a | 109.47 |
H1c16a—C16a—H2c16a | 109.47 | C25—C26—H1c26 | 109.47 |
H1c16a—C16a—H3c16a | 109.47 | C25—C26—H2c26 | 109.47 |
H2c16a—C16a—H3c16a | 109.47 | C25—C26—H3c26 | 109.47 |
C7a—C3a—C4a | 122.3 (2) | H1c26—C26—H2c26 | 109.47 |
C7a—C3a—C2a | 118.9 (2) | H1c26—C26—H3c26 | 109.47 |
C4a—C3a—C2a | 118.8 (2) | H2c26—C26—H3c26 | 109.47 |
C10b—C11b—C12b | 122.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3b—H1n3b···S1a | 0.866 (17) | 2.497 (19) | 3.3479 (19) | 168 (2) |
N1b—H1n1b···N4 | 0.86 (2) | 2.54 (2) | 3.229 (3) | 137.5 (19) |
N3a—H1n3a···S1ai | 0.87 (2) | 2.62 (2) | 3.430 (2) | 156 (2) |
N2a—H1n2a···S1b | 0.866 (17) | 2.57 (2) | 3.410 (2) | 163 (2) |
N2b—H1n2b···N4 | 0.865 (14) | 2.138 (14) | 2.994 (3) | 171 (2) |
N1a—H1n1a···S1ai | 0.869 (17) | 2.606 (16) | 3.435 (2) | 160.2 (18) |
C18b—H1c18b···N4 | 0.96 | 2.66 | 3.500 (4) | 146 |
Symmetry code: (i) −x+1, −y+2, −z+1. |
C21H24N3PS·C6H14N+·Cl− | F(000) = 1104 |
Mr = 517.1 | Dx = 1.203 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: -P 2yabc | Cell parameters from 25037 reflections |
a = 14.2245 (2) Å | θ = 3.7–67.1° |
b = 14.2802 (3) Å | µ = 2.56 mm−1 |
c = 14.8887 (3) Å | T = 120 K |
β = 109.2930 (16)° | Polygon crystal, white |
V = 2854.48 (10) Å3 | 0.25 × 0.21 × 0.17 mm |
Z = 4 |
Agilent Xcalibur (Atlas, Gemini ultra) diffractometer | 5073 independent reflections |
Radiation source: X-ray tube | 4567 reflections with I > 3σ(I) |
Mirror monochromator | Rint = 0.032 |
Detector resolution: 10.3745 pixels mm-1 | θmax = 67.1°, θmin = 3.7° |
ω scans | h = −16→16 |
Absorption correction: analytical (CrysAlis PRO; Agilent, 2014) | k = −17→16 |
Tmin = 0.950, Tmax = 0.970 | l = −17→17 |
48608 measured reflections |
Refinement on F2 | 171 constraints |
R[F2 > 2σ(F2)] = 0.029 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.094 | Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0016I2) |
S = 1.76 | (Δ/σ)max = 0.018 |
5073 reflections | Δρmax = 0.22 e Å−3 |
324 parameters | Δρmin = −0.21 e Å−3 |
11 restraints |
C21H24N3PS·C6H14N+·Cl− | V = 2854.48 (10) Å3 |
Mr = 517.1 | Z = 4 |
Monoclinic, P21/n | Cu Kα radiation |
a = 14.2245 (2) Å | µ = 2.56 mm−1 |
b = 14.2802 (3) Å | T = 120 K |
c = 14.8887 (3) Å | 0.25 × 0.21 × 0.17 mm |
β = 109.2930 (16)° |
Agilent Xcalibur (Atlas, Gemini ultra) diffractometer | 5073 independent reflections |
Absorption correction: analytical (CrysAlis PRO; Agilent, 2014) | 4567 reflections with I > 3σ(I) |
Tmin = 0.950, Tmax = 0.970 | Rint = 0.032 |
48608 measured reflections |
R[F2 > 2σ(F2)] = 0.029 | 11 restraints |
wR(F2) = 0.094 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.76 | Δρmax = 0.22 e Å−3 |
5073 reflections | Δρmin = −0.21 e Å−3 |
324 parameters |
Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement. The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cl1 | 0.65319 (3) | 0.28741 (2) | 0.11661 (2) | 0.02555 (12) | |
P1 | 0.69591 (3) | 0.00599 (2) | 0.22624 (2) | 0.01968 (12) | |
S1 | 0.60274 (3) | 0.00560 (2) | 0.09614 (2) | 0.02613 (13) | |
N1 | 0.66923 (9) | −0.06110 (8) | 0.30497 (8) | 0.0233 (4) | |
N3 | 0.80789 (9) | −0.03656 (8) | 0.23984 (8) | 0.0229 (4) | |
N2 | 0.70379 (9) | 0.11425 (8) | 0.26446 (8) | 0.0224 (4) | |
N4 | 0.44950 (9) | 0.82533 (9) | 0.07546 (8) | 0.0254 (4) | |
C10 | 0.77323 (11) | 0.28112 (11) | 0.46434 (11) | 0.0282 (5) | |
C1 | 0.58281 (10) | −0.05689 (10) | 0.33122 (9) | 0.0234 (4) | |
C16 | 0.86072 (11) | 0.07470 (10) | 0.13859 (10) | 0.0259 (5) | |
C15 | 0.87657 (11) | −0.00449 (9) | 0.19685 (10) | 0.0221 (5) | |
C6 | 0.56747 (12) | −0.12803 (11) | 0.38877 (11) | 0.0306 (5) | |
C20 | 0.96611 (11) | −0.05264 (11) | 0.21695 (10) | 0.0271 (5) | |
C13 | 0.82515 (10) | 0.10139 (10) | 0.42776 (10) | 0.0242 (5) | |
C8 | 0.75209 (10) | 0.15001 (10) | 0.35708 (9) | 0.0212 (4) | |
C11 | 0.84679 (11) | 0.23370 (11) | 0.53513 (10) | 0.0279 (5) | |
C17 | 0.93459 (12) | 0.10374 (11) | 0.10310 (10) | 0.0294 (5) | |
C5 | 0.48415 (12) | −0.12713 (12) | 0.41693 (11) | 0.0357 (6) | |
C22 | 0.51320 (11) | 0.75315 (11) | 0.13982 (10) | 0.0282 (5) | |
C4 | 0.41320 (12) | −0.05676 (12) | 0.38943 (11) | 0.0329 (5) | |
C12 | 0.87094 (11) | 0.14382 (11) | 0.51526 (10) | 0.0276 (5) | |
C18 | 1.02519 (12) | 0.05733 (11) | 0.12350 (11) | 0.0309 (5) | |
C24 | 0.29991 (11) | 0.77174 (12) | 0.11077 (11) | 0.0303 (5) | |
C9 | 0.72596 (11) | 0.23976 (10) | 0.37666 (10) | 0.0255 (5) | |
C2 | 0.51295 (11) | 0.01440 (11) | 0.30268 (11) | 0.0281 (5) | |
C23 | 0.36435 (11) | 0.85513 (11) | 0.10584 (10) | 0.0294 (5) | |
C25 | 0.36353 (12) | 0.69582 (12) | 0.17469 (11) | 0.0335 (6) | |
C19 | 1.03898 (12) | −0.02141 (12) | 0.18114 (11) | 0.0319 (5) | |
C3 | 0.42938 (12) | 0.01366 (12) | 0.33169 (11) | 0.0321 (6) | |
C27 | 0.21634 (14) | 0.80332 (17) | 0.14638 (14) | 0.0523 (8) | |
C26 | 0.45110 (12) | 0.66829 (11) | 0.14295 (11) | 0.0312 (5) | |
C14 | 0.89760 (13) | 0.28004 (13) | 0.63041 (12) | 0.0381 (6) | |
C21 | 1.10526 (13) | 0.09118 (14) | 0.08533 (13) | 0.0437 (7) | |
C7 | 0.32302 (13) | −0.05646 (15) | 0.42111 (13) | 0.0442 (7) | |
H1c10 | 0.754898 | 0.343398 | 0.476344 | 0.0338* | |
H1c16 | 0.799206 | 0.10871 | 0.123267 | 0.0311* | |
H1c6 | 0.615009 | −0.177954 | 0.408987 | 0.0367* | |
H1c20 | 0.977564 | −0.107853 | 0.255871 | 0.0325* | |
H1c13 | 0.843608 | 0.039092 | 0.415985 | 0.029* | |
H1c17 | 0.922729 | 0.158033 | 0.062858 | 0.0352* | |
H1c5 | 0.47509 | −0.17678 | 0.456767 | 0.0428* | |
H1c22 | 0.541289 | 0.778627 | 0.202714 | 0.0338* | |
H2c22 | 0.566009 | 0.735276 | 0.116541 | 0.0338* | |
H1c12 | 0.920965 | 0.109776 | 0.563559 | 0.0331* | |
H1c24 | 0.270549 | 0.745643 | 0.048306 | 0.0364* | |
H1c9 | 0.674755 | 0.273353 | 0.329073 | 0.0306* | |
H1c4 | 0.522212 | 0.064125 | 0.263026 | 0.0337* | |
H1c23 | 0.324816 | 0.90022 | 0.061481 | 0.0352* | |
H2c23 | 0.389194 | 0.884392 | 0.16723 | 0.0352* | |
H1c25 | 0.387887 | 0.717954 | 0.239166 | 0.0401* | |
H2c25 | 0.323149 | 0.641696 | 0.173637 | 0.0401* | |
H1c19 | 1.100662 | −0.05516 | 0.196631 | 0.0382* | |
H1c3 | 0.381489 | 0.063263 | 0.311217 | 0.0385* | |
H1c27 | 0.173088 | 0.751358 | 0.145086 | 0.0627* | |
H2c27 | 0.244155 | 0.826123 | 0.210386 | 0.0627* | |
H3c27 | 0.17904 | 0.852397 | 0.106143 | 0.0627* | |
H1c26 | 0.491602 | 0.623146 | 0.186539 | 0.0375* | |
H2c26 | 0.426691 | 0.640336 | 0.080888 | 0.0375* | |
H2c14a | 0.966777 | 0.263037 | 0.652927 | 0.0457* | 0.60 (3) |
H3c14a | 0.891593 | 0.34681 | 0.623334 | 0.0457* | 0.60 (3) |
H1c14a | 0.86663 | 0.259632 | 0.675359 | 0.0457* | 0.60 (3) |
H2c21 | 1.133871 | 0.147992 | 0.117237 | 0.0525* | |
H1c21 | 1.15616 | 0.044272 | 0.096234 | 0.0525* | |
H3c21 | 1.076653 | 0.102802 | 0.018269 | 0.0525* | |
H3c7a | 0.267304 | −0.030598 | 0.371623 | 0.0531* | 0.51 (2) |
H2c7a | 0.307886 | −0.11943 | 0.434315 | 0.0531* | 0.51 (2) |
H1c7a | 0.336394 | −0.019154 | 0.477602 | 0.0531* | 0.51 (2) |
H1n1 | 0.7079 (11) | −0.1075 (9) | 0.3293 (11) | 0.0279* | |
H1n3 | 0.8260 (12) | −0.0839 (9) | 0.2769 (10) | 0.0275* | |
H1n2 | 0.6780 (11) | 0.1536 (10) | 0.2199 (9) | 0.0268* | |
H1n4 | 0.4265 (12) | 0.8015 (11) | 0.0179 (8) | 0.0304* | |
H2n4 | 0.4885 (11) | 0.8727 (9) | 0.0739 (12) | 0.0304* | |
H1c7b | 0.301209 | 0.006831 | 0.423483 | 0.0531* | 0.49 (2) |
H2c7b | 0.270544 | −0.091851 | 0.376878 | 0.0531* | 0.49 (2) |
H3c7b | 0.339832 | −0.084163 | 0.483179 | 0.0531* | 0.49 (2) |
H1c14b | 0.90171 | 0.236416 | 0.680631 | 0.0457* | 0.40 (3) |
H2c14b | 0.963458 | 0.299248 | 0.634133 | 0.0457* | 0.40 (3) |
H3c25b | 0.859832 | 0.333815 | 0.636857 | 0.0457* | 0.40 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0337 (2) | 0.02031 (19) | 0.01919 (18) | −0.00368 (12) | 0.00410 (14) | −0.00158 (11) |
P1 | 0.02053 (19) | 0.0173 (2) | 0.01818 (19) | −0.00150 (12) | 0.00233 (14) | 0.00186 (12) |
S1 | 0.0269 (2) | 0.0236 (2) | 0.0215 (2) | −0.00514 (13) | −0.00064 (15) | 0.00217 (12) |
N1 | 0.0221 (6) | 0.0211 (6) | 0.0241 (6) | 0.0011 (5) | 0.0042 (5) | 0.0062 (5) |
N3 | 0.0247 (6) | 0.0187 (6) | 0.0238 (6) | 0.0013 (5) | 0.0059 (5) | 0.0048 (5) |
N2 | 0.0254 (6) | 0.0183 (6) | 0.0190 (6) | 0.0010 (4) | 0.0015 (5) | 0.0033 (4) |
N4 | 0.0297 (6) | 0.0238 (7) | 0.0215 (6) | −0.0050 (5) | 0.0069 (5) | −0.0019 (5) |
C10 | 0.0336 (8) | 0.0252 (8) | 0.0284 (8) | −0.0024 (6) | 0.0137 (6) | −0.0044 (6) |
C1 | 0.0247 (7) | 0.0240 (7) | 0.0191 (6) | −0.0051 (5) | 0.0037 (5) | −0.0023 (5) |
C16 | 0.0262 (7) | 0.0240 (8) | 0.0249 (7) | −0.0009 (6) | 0.0051 (6) | 0.0000 (6) |
C15 | 0.0237 (7) | 0.0213 (7) | 0.0192 (7) | −0.0029 (5) | 0.0041 (6) | −0.0036 (5) |
C6 | 0.0348 (8) | 0.0257 (8) | 0.0306 (8) | −0.0020 (6) | 0.0099 (6) | 0.0048 (6) |
C20 | 0.0302 (7) | 0.0225 (8) | 0.0270 (7) | 0.0006 (6) | 0.0072 (6) | −0.0031 (6) |
C13 | 0.0240 (7) | 0.0230 (8) | 0.0239 (7) | 0.0008 (5) | 0.0059 (6) | 0.0013 (5) |
C8 | 0.0213 (6) | 0.0217 (7) | 0.0203 (6) | −0.0038 (5) | 0.0063 (5) | −0.0001 (5) |
C11 | 0.0268 (7) | 0.0348 (8) | 0.0235 (7) | −0.0053 (6) | 0.0103 (6) | −0.0052 (6) |
C17 | 0.0370 (8) | 0.0252 (8) | 0.0254 (7) | −0.0069 (6) | 0.0096 (6) | −0.0015 (6) |
C5 | 0.0415 (9) | 0.0345 (9) | 0.0335 (8) | −0.0081 (7) | 0.0156 (7) | 0.0038 (7) |
C22 | 0.0240 (7) | 0.0347 (9) | 0.0234 (7) | 0.0037 (6) | 0.0046 (6) | −0.0006 (6) |
C4 | 0.0335 (8) | 0.0381 (9) | 0.0294 (8) | −0.0081 (7) | 0.0134 (6) | −0.0058 (6) |
C12 | 0.0249 (7) | 0.0334 (9) | 0.0222 (7) | 0.0000 (6) | 0.0046 (6) | 0.0014 (6) |
C18 | 0.0351 (8) | 0.0300 (8) | 0.0306 (8) | −0.0083 (6) | 0.0150 (6) | −0.0117 (6) |
C24 | 0.0243 (7) | 0.0415 (9) | 0.0243 (7) | 0.0014 (6) | 0.0069 (6) | −0.0004 (6) |
C9 | 0.0271 (7) | 0.0245 (8) | 0.0240 (7) | 0.0012 (6) | 0.0073 (6) | 0.0023 (6) |
C2 | 0.0294 (8) | 0.0267 (8) | 0.0282 (8) | −0.0007 (6) | 0.0095 (6) | 0.0041 (6) |
C23 | 0.0347 (8) | 0.0259 (8) | 0.0255 (7) | 0.0063 (6) | 0.0074 (6) | −0.0017 (6) |
C25 | 0.0364 (8) | 0.0347 (9) | 0.0297 (8) | −0.0034 (7) | 0.0116 (7) | 0.0069 (6) |
C19 | 0.0287 (8) | 0.0315 (8) | 0.0361 (9) | 0.0012 (6) | 0.0116 (7) | −0.0091 (7) |
C3 | 0.0289 (8) | 0.0343 (9) | 0.0328 (8) | 0.0020 (6) | 0.0097 (7) | −0.0013 (6) |
C27 | 0.0367 (10) | 0.0848 (16) | 0.0382 (10) | 0.0120 (9) | 0.0162 (8) | 0.0008 (9) |
C26 | 0.0371 (8) | 0.0269 (8) | 0.0267 (7) | 0.0059 (6) | 0.0067 (6) | 0.0054 (6) |
C14 | 0.0379 (9) | 0.0453 (10) | 0.0288 (8) | −0.0019 (7) | 0.0079 (7) | −0.0119 (7) |
C21 | 0.0468 (10) | 0.0444 (11) | 0.0496 (10) | −0.0114 (8) | 0.0288 (9) | −0.0134 (8) |
C7 | 0.0404 (10) | 0.0545 (12) | 0.0450 (10) | −0.0077 (8) | 0.0238 (8) | −0.0040 (8) |
Cl1—N1i | 3.2365 (12) | C12—H1c12 | 0.96 |
Cl1—N3i | 3.2266 (12) | C18—C19 | 1.389 (2) |
Cl1—N2 | 3.2296 (12) | C18—C21 | 1.511 (3) |
Cl1—N4ii | 3.1848 (12) | C24—C23 | 1.519 (2) |
P1—S1 | 1.9524 (4) | C24—C25 | 1.527 (2) |
P1—N1 | 1.6523 (14) | C24—C27 | 1.521 (3) |
P1—N3 | 1.6536 (13) | C24—H1c24 | 0.96 |
P1—N2 | 1.6383 (12) | C9—H1c9 | 0.96 |
N1—C1 | 1.409 (2) | C2—C3 | 1.392 (3) |
N1—H1n1 | 0.861 (13) | C2—H1c4 | 0.96 |
N3—C15 | 1.410 (2) | C23—H1c23 | 0.96 |
N3—H1n3 | 0.857 (13) | C23—H2c23 | 0.96 |
N2—C8 | 1.4171 (16) | C25—C26 | 1.523 (3) |
N2—H1n2 | 0.854 (13) | C25—H1c25 | 0.96 |
N4—C22 | 1.4926 (18) | C25—H2c25 | 0.96 |
N4—C23 | 1.488 (2) | C19—H1c19 | 0.96 |
N4—H1n4 | 0.878 (12) | C3—H1c3 | 0.96 |
N4—H2n4 | 0.879 (15) | C27—H1c27 | 0.96 |
C10—C11 | 1.3912 (19) | C27—H2c27 | 0.96 |
C10—C9 | 1.387 (2) | C27—H3c27 | 0.96 |
C10—H1c10 | 0.96 | C26—H1c26 | 0.96 |
C1—C6 | 1.392 (2) | C26—H2c26 | 0.96 |
C1—C2 | 1.388 (2) | C14—H2c14a | 0.96 |
C16—C15 | 1.398 (2) | C14—H3c14a | 0.96 |
C16—C17 | 1.386 (2) | C14—H1c14a | 0.96 |
C16—H1c16 | 0.96 | C14—H1c14b | 0.96 |
C15—C20 | 1.390 (2) | C14—H2c14b | 0.96 |
C6—C5 | 1.382 (3) | C14—H3c25b | 0.96 |
C6—H1c6 | 0.96 | C21—H2c21 | 0.96 |
C20—C19 | 1.387 (3) | C21—H1c21 | 0.96 |
C20—H1c20 | 0.96 | C21—H3c21 | 0.96 |
C13—C8 | 1.3952 (17) | C7—H3c7a | 0.96 |
C13—C12 | 1.3884 (19) | C7—H2c7a | 0.96 |
C13—H1c13 | 0.96 | C7—H1c7a | 0.96 |
C8—C9 | 1.392 (2) | C7—H1c7b | 0.96 |
C11—C12 | 1.386 (2) | C7—H2c7b | 0.96 |
C11—C14 | 1.515 (2) | C7—H3c7b | 0.96 |
C17—C18 | 1.391 (2) | H2c14a—H2c14b | 0.5824 |
C17—H1c17 | 0.96 | H3c14a—H3c25b | 0.5824 |
C5—C4 | 1.387 (2) | H1c14a—H1c14b | 0.5824 |
C5—H1c5 | 0.96 | H3c7a—H1c7b | 0.9319 |
C22—C26 | 1.509 (2) | H3c7a—H2c7b | 0.8781 |
C22—H1c22 | 0.96 | H2c7a—H2c7b | 0.9319 |
C22—H2c22 | 0.96 | H2c7a—H3c7b | 0.878 |
C4—C3 | 1.391 (2) | H1c7a—H1c7b | 0.878 |
C4—C7 | 1.506 (3) | H1c7a—H3c7b | 0.9319 |
N1i—Cl1—N3i | 45.38 (3) | N4—C23—H1c23 | 109.47 |
N1i—Cl1—N2 | 107.11 (3) | N4—C23—H2c23 | 109.47 |
N1i—Cl1—N4ii | 137.18 (4) | C24—C23—H1c23 | 109.47 |
N3i—Cl1—N2 | 101.20 (3) | C24—C23—H2c23 | 109.47 |
N3i—Cl1—N4ii | 156.34 (3) | H1c23—C23—H2c23 | 108.1 |
N2—Cl1—N4ii | 99.08 (3) | C24—C25—C26 | 111.54 (14) |
S1—P1—N1 | 117.55 (4) | C24—C25—H1c25 | 109.47 |
S1—P1—N3 | 115.54 (5) | C24—C25—H2c25 | 109.47 |
S1—P1—N2 | 107.06 (4) | C26—C25—H1c25 | 109.47 |
N1—P1—N3 | 97.91 (6) | C26—C25—H2c25 | 109.47 |
N1—P1—N2 | 107.83 (7) | H1c25—C25—H2c25 | 107.32 |
N3—P1—N2 | 110.58 (6) | C20—C19—C18 | 121.82 (15) |
Cl1iii—N1—P1 | 107.98 (6) | C20—C19—H1c19 | 119.09 |
Cl1iii—N1—C1 | 125.24 (8) | C18—C19—H1c19 | 119.09 |
Cl1iii—N1—H1n1 | 11.4 (11) | C4—C3—C2 | 122.00 (15) |
P1—N1—C1 | 126.73 (9) | C4—C3—H1c3 | 119 |
P1—N1—H1n1 | 118.7 (12) | C2—C3—H1c3 | 119 |
C1—N1—H1n1 | 114.2 (12) | C24—C27—H1c27 | 109.47 |
Cl1iii—N3—P1 | 108.36 (6) | C24—C27—H2c27 | 109.47 |
Cl1iii—N3—C15 | 124.12 (8) | C24—C27—H3c27 | 109.47 |
Cl1iii—N3—H1n3 | 7.8 (12) | H1c27—C27—H2c27 | 109.47 |
P1—N3—C15 | 127.52 (9) | H1c27—C27—H3c27 | 109.47 |
P1—N3—H1n3 | 116.1 (12) | H2c27—C27—H3c27 | 109.47 |
C15—N3—H1n3 | 116.3 (12) | C22—C26—C25 | 110.45 (13) |
Cl1—N2—P1 | 120.76 (5) | C22—C26—H1c26 | 109.47 |
Cl1—N2—C8 | 108.34 (8) | C22—C26—H2c26 | 109.47 |
Cl1—N2—H1n2 | 12.9 (10) | C25—C26—H1c26 | 109.47 |
P1—N2—C8 | 129.31 (9) | C25—C26—H2c26 | 109.47 |
P1—N2—H1n2 | 112.8 (9) | H1c26—C26—H2c26 | 108.48 |
C8—N2—H1n2 | 117.7 (9) | C11—C14—H2c14a | 109.47 |
Cl1ii—N4—C22 | 103.21 (8) | C11—C14—H3c14a | 109.47 |
Cl1ii—N4—C23 | 103.86 (7) | C11—C14—H1c14a | 109.47 |
Cl1ii—N4—H1n4 | 10.2 (11) | C11—C14—H1c14b | 109.47 |
Cl1ii—N4—H2n4 | 118.1 (12) | C11—C14—H2c14b | 109.47 |
C22—N4—C23 | 112.63 (12) | C11—C14—H3c25b | 109.47 |
C22—N4—H1n4 | 108.0 (10) | H2c14a—C14—H3c14a | 109.47 |
C22—N4—H2n4 | 107.1 (9) | H2c14a—C14—H1c14a | 109.47 |
C23—N4—H1n4 | 109.2 (12) | H2c14a—C14—H1c14b | 76.84 |
C23—N4—H2n4 | 111.8 (11) | H2c14a—C14—H2c14b | 35.32 |
H1n4—N4—H2n4 | 107.9 (16) | H2c14a—C14—H3c25b | 135.26 |
C11—C10—C9 | 121.00 (14) | H3c14a—C14—H1c14a | 109.47 |
C11—C10—H1c10 | 119.5 | H3c14a—C14—H1c14b | 135.26 |
C9—C10—H1c10 | 119.5 | H3c14a—C14—H2c14b | 76.84 |
N1—C1—C6 | 117.92 (13) | H3c14a—C14—H3c25b | 35.32 |
N1—C1—C2 | 123.27 (14) | H1c14a—C14—H1c14b | 35.32 |
C6—C1—C2 | 118.81 (15) | H1c14a—C14—H2c14b | 135.26 |
C15—C16—C17 | 119.44 (14) | H1c14a—C14—H3c25b | 76.84 |
C15—C16—H1c16 | 120.28 | H1c14b—C14—H2c14b | 109.47 |
C17—C16—H1c16 | 120.28 | H1c14b—C14—H3c25b | 109.47 |
N3—C15—C16 | 123.43 (13) | H2c14b—C14—H3c25b | 109.47 |
N3—C15—C20 | 117.69 (13) | C18—C21—H2c21 | 109.47 |
C16—C15—C20 | 118.84 (15) | C18—C21—H1c21 | 109.47 |
C1—C6—C5 | 120.31 (14) | C18—C21—H3c21 | 109.47 |
C1—C6—H1c6 | 119.85 | H2c21—C21—H1c21 | 109.47 |
C5—C6—H1c6 | 119.85 | H2c21—C21—H3c21 | 109.47 |
C15—C20—C19 | 120.41 (14) | H1c21—C21—H3c21 | 109.47 |
C15—C20—H1c20 | 119.79 | C4—C7—H3c7a | 109.47 |
C19—C20—H1c20 | 119.79 | C4—C7—H2c7a | 109.47 |
C8—C13—C12 | 119.49 (14) | C4—C7—H1c7a | 109.47 |
C8—C13—H1c13 | 120.26 | C4—C7—H1c7b | 109.47 |
C12—C13—H1c13 | 120.26 | C4—C7—H2c7b | 109.47 |
N2—C8—C13 | 123.75 (13) | C4—C7—H3c7b | 109.47 |
N2—C8—C9 | 117.29 (11) | H3c7a—C7—H2c7a | 109.47 |
C13—C8—C9 | 118.95 (12) | H3c7a—C7—H1c7a | 109.47 |
C10—C11—C12 | 117.81 (13) | H3c7a—C7—H1c7b | 58.07 |
C10—C11—C14 | 120.23 (14) | H3c7a—C7—H2c7b | 54.43 |
C12—C11—C14 | 121.95 (13) | H3c7a—C7—H3c7b | 141.01 |
C16—C17—C18 | 122.59 (14) | H2c7a—C7—H1c7a | 109.47 |
C16—C17—H1c17 | 118.71 | H2c7a—C7—H1c7b | 141.01 |
C18—C17—H1c17 | 118.71 | H2c7a—C7—H2c7b | 58.07 |
C6—C5—C4 | 122.05 (16) | H2c7a—C7—H3c7b | 54.43 |
C6—C5—H1c5 | 118.97 | H1c7a—C7—H1c7b | 54.43 |
C4—C5—H1c5 | 118.97 | H1c7a—C7—H2c7b | 141.01 |
N4—C22—C26 | 109.68 (11) | H1c7a—C7—H3c7b | 58.07 |
N4—C22—H1c22 | 109.47 | H1c7b—C7—H2c7b | 109.47 |
N4—C22—H2c22 | 109.47 | H1c7b—C7—H3c7b | 109.47 |
C26—C22—H1c22 | 109.47 | H2c7b—C7—H3c7b | 109.47 |
C26—C22—H2c22 | 109.47 | C14—H2c14a—H2c14b | 72.34 |
H1c22—C22—H2c22 | 109.26 | C14—H3c14a—H3c25b | 72.34 |
C5—C4—C3 | 116.97 (17) | C14—H1c14a—H1c14b | 72.34 |
C5—C4—C7 | 121.45 (16) | C7—H3c7a—H1c7b | 60.96 |
C3—C4—C7 | 121.58 (15) | C7—H3c7a—H2c7b | 62.79 |
C13—C12—C11 | 122.13 (12) | H1c7b—H3c7a—H2c7b | 120 |
C13—C12—H1c12 | 118.93 | C7—H2c7a—H2c7b | 60.96 |
C11—C12—H1c12 | 118.93 | C7—H2c7a—H3c7b | 62.79 |
C17—C18—C19 | 116.90 (16) | H2c7b—H2c7a—H3c7b | 120 |
C17—C18—C21 | 121.66 (14) | C7—H1c7a—H1c7b | 62.79 |
C19—C18—C21 | 121.44 (15) | C7—H1c7a—H3c7b | 60.96 |
C23—C24—C25 | 110.11 (12) | H1c7b—H1c7a—H3c7b | 120 |
C23—C24—C27 | 109.76 (15) | C7—H1c7b—H3c7a | 60.96 |
C23—C24—H1c24 | 109.5 | C7—H1c7b—H1c7a | 62.79 |
C25—C24—C27 | 111.33 (15) | H3c7a—H1c7b—H1c7a | 120 |
C25—C24—H1c24 | 107.86 | C7—H2c7b—H3c7a | 62.79 |
C27—C24—H1c24 | 108.23 | C7—H2c7b—H2c7a | 60.97 |
C10—C9—C8 | 120.61 (12) | H3c7a—H2c7b—H2c7a | 120 |
C10—C9—H1c9 | 119.7 | C7—H3c7b—H2c7a | 62.79 |
C8—C9—H1c9 | 119.7 | C7—H3c7b—H1c7a | 60.96 |
C1—C2—C3 | 119.86 (15) | H2c7a—H3c7b—H1c7a | 120 |
C1—C2—H1c4 | 120.07 | C14—H1c14b—H1c14a | 72.34 |
C3—C2—H1c4 | 120.07 | C14—H2c14b—H2c14a | 72.34 |
N4—C23—C24 | 110.81 (13) | C14—H3c25b—H3c14a | 72.34 |
Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z; (iii) −x+3/2, y−1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1n1···Cl1iii | 0.861 (14) | 2.399 (15) | 3.2365 (13) | 164.5 (14) |
N3—H1n3···Cl1iii | 0.857 (13) | 2.381 (13) | 3.2267 (12) | 169.4 (16) |
N2—H1n2···Cl1 | 0.854 (14) | 2.405 (14) | 3.2298 (12) | 162.6 (14) |
N4—H1n4···Cl1ii | 0.879 (12) | 2.325 (13) | 3.1848 (12) | 165.9 (15) |
N4—H2n4···S1iv | 0.880 (15) | 2.449 (14) | 3.3211 (14) | 171.2 (15) |
Symmetry codes: (ii) −x+1, −y+1, −z; (iii) −x+3/2, y−1/2, −z+1/2; (iv) x, y+1, z. |
Experimental details
(I) | (II) | |
Crystal data | ||
Chemical formula | 2C24H30N3PS·C2H3N | C21H24N3PS·C6H14N+·Cl− |
Mr | 888.2 | 517.1 |
Crystal system, space group | Triclinic, P1 | Monoclinic, P21/n |
Temperature (K) | 120 | 120 |
a, b, c (Å) | 11.8547 (5), 13.5312 (4), 15.3394 (6) | 14.2245 (2), 14.2802 (3), 14.8887 (3) |
α, β, γ (°) | 91.849 (3), 98.378 (3), 94.991 (3) | 90, 109.2930 (16), 90 |
V (Å3) | 2422.56 (16) | 2854.48 (10) |
Z | 2 | 4 |
Radiation type | Cu Kα | Cu Kα |
µ (mm−1) | 1.94 | 2.56 |
Crystal size (mm) | 0.19 × 0.17 × 0.11 | 0.25 × 0.21 × 0.17 |
Data collection | ||
Diffractometer | Agilent Xcalibur (Atlas, Gemini ultra) diffractometer | Agilent Xcalibur (Atlas, Gemini ultra) diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2014) | Analytical (CrysAlis PRO; Agilent, 2014) |
Tmin, Tmax | 0.658, 1 | 0.950, 0.970 |
No. of measured, independent and observed [I > 3σ(I)] reflections | 15711, 8394, 6369 | 48608, 5073, 4567 |
Rint | 0.042 | 0.032 |
(sin θ/λ)max (Å−1) | 0.598 | 0.598 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.053, 1.45 | 0.029, 0.094, 1.76 |
No. of reflections | 8394 | 5073 |
No. of parameters | 568 | 324 |
No. of restraints | 6 | 11 |
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 |
Δρmax, Δρmin (e Å−3) | 0.36, −0.26 | 0.22, −0.21 |
Computer programs: (CrysAlis PRO; Agilent, 2014), SUPERFLIP (Palatinus & Chapuis, 2007), JANA2006 (Petříček et al., 2014), Mercury (Macrae et al., 2008), enCIFer (Allen et al., 2004).
S1a—P1a | 1.9643 (8) | N2a—C9a | 1.427 (3) |
P1a—N2a | 1.635 (2) | N3b—C17b | 1.425 (3) |
P1a—N1a | 1.655 (2) | N1b—C1b | 1.409 (3) |
P1a—N3a | 1.6523 (18) | N1a—C1a | 1.412 (3) |
S1b—P1b | 1.9501 (8) | N2b—C9b | 1.406 (3) |
P1b—N3b | 1.646 (2) | N3a—C17a | 1.421 (3) |
P1b—N1b | 1.6591 (19) | N4—C25 | 1.128 (4) |
P1b—N2b | 1.652 (2) | ||
S1a—P1a—N2a | 108.21 (7) | N3b—P1b—N1b | 108.65 (10) |
S1a—P1a—N1a | 115.88 (8) | N3b—P1b—N2b | 109.73 (10) |
S1a—P1a—N3a | 116.27 (7) | N1b—P1b—N2b | 97.25 (10) |
N2a—P1a—N1a | 108.72 (10) | P1a—N2a—C9a | 128.87 (15) |
N2a—P1a—N3a | 108.38 (10) | P1b—N3b—C17b | 128.04 (15) |
N1a—P1a—N3a | 98.85 (9) | P1b—N1b—C1b | 127.14 (16) |
S1b—P1b—N3b | 108.31 (7) | P1a—N1a—C1a | 126.46 (15) |
S1b—P1b—N1b | 115.80 (8) | P1b—N2b—C9b | 129.06 (16) |
S1b—P1b—N2b | 116.55 (8) | P1a—N3a—C17a | 126.12 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3b—H1n3b···S1a | 0.866 (17) | 2.497 (19) | 3.3479 (19) | 168 (2) |
N1b—H1n1b···N4 | 0.86 (2) | 2.54 (2) | 3.229 (3) | 137.5 (19) |
N3a—H1n3a···S1ai | 0.87 (2) | 2.62 (2) | 3.430 (2) | 156 (2) |
N2a—H1n2a···S1b | 0.866 (17) | 2.57 (2) | 3.410 (2) | 163 (2) |
N2b—H1n2b···N4 | 0.865 (14) | 2.138 (14) | 2.994 (3) | 171 (2) |
N1a—H1n1a···S1ai | 0.869 (17) | 2.606 (16) | 3.435 (2) | 160.2 (18) |
Symmetry code: (i) −x+1, −y+2, −z+1. |
P1—S1 | 1.9524 (4) | N3—C15 | 1.410 (2) |
P1—N1 | 1.6523 (14) | N2—C8 | 1.4171 (16) |
P1—N3 | 1.6536 (13) | N4—C22 | 1.4926 (18) |
P1—N2 | 1.6383 (12) | N4—C23 | 1.488 (2) |
N1—C1 | 1.409 (2) | ||
S1—P1—N1 | 117.55 (4) | N3—P1—N2 | 110.58 (6) |
S1—P1—N3 | 115.54 (5) | P1—N1—C1 | 126.73 (9) |
S1—P1—N2 | 107.06 (4) | P1—N3—C15 | 127.52 (9) |
N1—P1—N3 | 97.91 (6) | P1—N2—C8 | 129.31 (9) |
N1—P1—N2 | 107.83 (7) | C22—N4—C23 | 112.63 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1n1···Cl1i | 0.861 (14) | 2.399 (15) | 3.2365 (13) | 164.5 (14) |
N3—H1n3···Cl1i | 0.857 (13) | 2.381 (13) | 3.2267 (12) | 169.4 (16) |
N2—H1n2···Cl1 | 0.854 (14) | 2.405 (14) | 3.2298 (12) | 162.6 (14) |
N4—H1n4···Cl1ii | 0.879 (12) | 2.325 (13) | 3.1848 (12) | 165.9 (15) |
N4—H2n4···S1iii | 0.880 (15) | 2.449 (14) | 3.3211 (14) | 171.2 (15) |
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z; (iii) x, y+1, z. |
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