research communications
S)-ABOC-(S)-Ala-(S)-ABOC-(S)-Phe-OBn chloroform monosolvate
of Boc-(aUniversité de Lorraine, UMR 7036 CRM2, Vandoeuvre-lès-Nancy, France, bCNRS, UMR 7036 CRM2, Vandoeuvre-lès-Nancy, France, and cIBMM, UMR 5247 CNRS-Université Montpellier–ENSCM, 15 avenue Charles Flahault, 34093 Montpellier Cedex 5, France
*Correspondence e-mail: claude.didierjean@univ-lorraine.fr
In the title compound, phenyl (S)-2-[(S)-(1-{2-[(S)-(1-{[(tert-butoxy)carbonyl]amino}bicyclo[2.2.2]octan-2-yl)formamido]propanamido}bicyclo[2.2.2]octan-2-yl)formamido]-3-phenylpropanoate chloroform monosolvate, C42H56N4O7·CHCl3, the α,β-hybrid peptide contains two non-proteinogenic amino acid residues of (S)-1-aminobicyclo[2.2.2]octane-2-carboxylic acid [(S)-ABOC], two amino acid residues of (S)-2-aminopropanoic acid [(S)-Ala] and (S)-2-amino-3-phenylpropanoic acid [(S)-Phe], and protecting groups of tert-butoxycarbonyl (Boc) and benzyl ester (OBn). The tetramer folds into a right-handed mixed 11/9 helix stabilized by intramolecular i,i + 3 and i,i − 1 C=O⋯H—N hydrogen bonds. In the crystal, the oligomers are linked by N—H⋯O=C hydrogen bonds into chains along the a-axis direction. The chloroform solvent molecules are intercalated between the folded chains via C—H⋯O=C interactions.
Keywords: crystal structure; α,β-hybrid peptide; (S)-1-aminobicyclo[2.2.2]octane-2-carboxylic acid; (S)-ABOC; (S)-Ala; (S)-Phe; Boc; OBn; 11/9 helix; hydrogen bonding.
CCDC reference: 1423394
1. Chemical context
The title compound is an α,β-hybrid tetrapeptide with alternating proteogenic α-amino acid and ABOC residues. (S)-1-aminobicyclo[2.2.2]octane-2-carboxylic acid [(S)-ABOC] is a β2,3,3-trisubstituted bicyclic amino acid which exhibits a high propensity to induce both a reverse turn into short and helices in oligoureas and in α,β-hybrid (Songis et al., 2007; André et al., 2012, 2013; Legrand et al., 2012, 2014). In our last study we showed that short oligomers adopted an 11/9 helix, whereas an 18/16 helix was favored for longer oligomers in solution. NMR studies suggested a rapid interconversion between the 11/9 helix and the 18/16 helix for oligomers of intermediate length. In the solid state, only the 11/9 helix has been observed whatever the length of the oligomers capped by an iPrCO and an OBn group (Legrand et al., 2014).
2. Structural commentary
For the title compound (Fig. 1), the triclinic consists of one molecule of α,β-hybrid tetramer and one molecule of chloroform. The oligomer exhibits a right-handed mixed 11/9 helix stabilized by backbone C=O⋯HN hydrogen bonds (Table 1), forming one C11 pseudocycle between the CO of the β-residue (i) and the NH of the α-residue (i + 3) and two C9 pseudocycles between the CO of the α-residue (i) and the NH of the β-residue (i − 1). The backbone torsion angles are quite similar to those of the characteristic 11/9 helix reported in the same α,β-hybrid oligomers (Legrand et al., 2014) and other α/β-peptides (Lee et al., 2013).
3. Supramolecular features
The intermolecular interaction N2—H2⋯O5i (Table 1) connects the title α,β-hybrid tetramer to form infinite chains along the a-axis direction (Fig. 2). In the ac plane the chloroform molecules link the chains via a C—Cl⋯N interaction [Cl⋯N = 3.281 (3) Å] and a C—H⋯O hydrogen bond [C⋯O = 3.071 (4) Å].
4. Comparison with related structures
The crystals of the title compound and those of the same tetramer with the N-terminal capping group iPrCO instead of Boc are not isomorphous. This latter crystallized in the P21 with two independent molecules in the One independent molecule shows a single fully folded 11/9 helix as the title compound while the hydrogen-bond network is incomplete in the other molecule. The last C9 hydrogen bond between the carbonyl of the Phe residue and the β-residue amide proton was disrupted by the incorporation of a water molecule (Legrand et al., 2014). This intercalation of water molecules has already been observed in oligoureas (Legrand et al., 2012) and highlighted in an enzyme involved in the mitochondrial respiratory chain i.e. the mitochondrial bc1 complex. Its bovine (Huang et al., 2005) revealed that an intercalated water molecule in an α-helix took part in the stabilization of the high potential cytochrome b heme. Usually, α-helices interact laterally with their side chains. Water molecules adsorption on an α-helice groove is an alternative tool available to the helical system to interact with partners.
For further related articles on hybrid et al. (2004); Sharma et al. (2009); Vasudev et al. (2011); Berlicki et al. (2012);
see: Hayen5. Synthesis and crystallization
The synthesis of the title compound has recently been reported by Legrand et al. (2014). Single crystals were obtained by slow evaporation of a chloroform solution.
6. Refinement
Crystal data, data collection and structure . All H atoms were located in a difference Fourier map. The C/N-bonded H atoms were placed at calculated positions and refined using a riding model, with C—H = 0.95–1.00 Å and N—H = 0.88 Å. The Uiso(H) parameters were fixed at 1.2Ueq(C, N) for methine, methylene, aromatic groups and NH groups, and at 1.5Ueq(C) for methyl groups.
details are summarized in Table 2Supporting information
CCDC reference: 1423394
10.1107/S2056989015016941/is5415sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989015016941/is5415Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015016941/is5415Isup3.cml
The title compound is an α,β-hybrid tetrapeptide with alternating proteogenic α-amino acid and ABOC residues. (S)-1-aminobicyclo[2.2.2]octane-2-carboxylic acid [(S)-ABOC] is a β2,3,3-trisubstituted bicyclic amino acid which exhibits a high propensity to induce both a reverse turn into short and helices in oligoureas and in α,β-hybrid (Songis et al., 2007; André et al., 2012, 2013; Legrand et al., 2012, 2014). In our last study we showed that short oligomers adopted an 11/9 helix, whereas an 18/16 helix was favored for longer oligomers in solution. NMR studies suggested a rapid interconversion between the 11/9 helix and the 18/16 helix for oligomers of intermediate length. In the solid state, only the 11/9 helix has been observed whatever the length of the oligomers capped by an iPrCO and an OBn group (Legrand et al., 2014).
For the title compound (Fig. 1), the triclinic α,β-hybrid tetramer and one molecule of chloroform. The oligomer exhibits a right-handed mixed 11/9 helix stabilized by backbone C═O···HN hydrogen bonds (Table 1), forming one C11 pseudocycle between the CO of the β-residue (i) and the NH of the α-residue (i+3) and two C9 pseudocycles between the CO of the α-residue (i) and the NH of the β-residue (i-1). The backbone torsion angles are quite similar to those of the characteristic 11/9 helix reported in the same α,β-hybrid oligomers (Legrand et al., 2014) and other α/β-peptides (Lee et al., 2013).
consists of one molecule ofThe crystals of the title compound and those of the same tetramer with the N-terminal capping group iPrCO instead of Boc are not isomorphous. This latter crystallized in the β-residue amide proton was disrupted by the incorporation of a water molecule (Legrand et al., 2014). This intercalation of water molecules has already been observed in oligoureas (Legrand et al., 2012) and highlighted in an enzyme involved in the mitochondrial respiratory chain i.e. the mitochondrial bc1 complex. Its bovine (Huang et al., 2005) revealed that an intercalated water molecule in an α-helix took part in the stabilization of the high potential cytochrome b heme. Usually, α-helices interact laterally with their side chains. Water molecules adsorption on an α-helice groove is an alternative tool available to the helical system to interact with partners.
P21 with two independent molecules in the One independent molecule shows a single fully folded 11/9 helix as the title compound while the hydrogen-bond network is incomplete in the other molecule. The last C9 hydrogen bond between the carbonyl of the Phe residue and theThe intermolecular interaction N2—H2···O5i (Table 1) connects the title α,β-hybrid tetramer to form infinite chains along the a-axis direction. In the plane perpendicular to the b* axis the chloroform molecules link the chains via a C—Cl···N interaction [Cl···N = 3.281 (3) Å] and a C—H···O hydrogen bond [C···O = 3.071 (4) Å].
The crystals of the title compound and those of the same tetramer with the N-terminal capping group iPrCO instead of Boc are not isomorphous. This latter crystallized in the β-residue amide proton was disrupted by the incorporation of a water molecule (Legrand et al., 2014). This intercalation of water molecules has already been observed in oligoureas (Legrand et al., 2012) and highlighted in an enzyme involved in the mitochondrial respiratory chain i.e. the mitochondrial bc1 complex. Its bovine (Huang et al., 2005) revealed that an intercalated water molecule in an α-helix took part in the stabilization of the high potential cytochrome b heme. Usually, α-helices interact laterally with their side chains. Water molecules adsorption on an α-helice groove is an alternative tool available to the helical system to interact with partners.
P21 with two independent molecules in the One independent molecule shows a single fully folded 11/9 helix as the title compound while the hydrogen-bond network is incomplete in the other molecule. The last C9 hydrogen bond between the carbonyl of the Phe residue and theFor further related articles on hybrid
see: Hayen et al. (2004); Sharma et al. (2009); Vasudev et al. (2011); Berlicki et al. (2012);The synthesis of the title compound has recently been reported by Legrand et al. (2014). Single crystals were obtained by slow evaporation of a chloroform solution.
Crystal data, data collection and structure
details are summarized in Table 2. All H atoms were located in a difference Fourier map. The C/N-bonded H atoms were placed at calculated positions and refined using a riding model, with C—H = 0.95–1.00 Å and N—H = 0.88 Å. The Uiso(H) parameters were fixed at 1.2Ueq(C, N) for methine, methylene, aromatic groups and NH groups, and at 1.5Ueq(C) for methyl groups.Data collection: APEX2 (Bruker, 2014); cell
SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SIR2008 (Burla et al., 2007); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008) and pyMOL (DeLano, 2002); software used to prepare material for publication: WinGX (Farrugia, 2012) and enCIFer (Allen et al., 2004).Fig. 1. The molecular structure of the title compound showing the atom-numbering scheme. All non-H atoms are represented by 25% probability displacement ellipsoids. H atoms are omitted for clarity. | |
Fig. 2. Partial packing view of the title compound in the ac plane. Only selected H atoms are shown for clarity. Intramolecular hydrogen bonds are shown as magenta dashed lines. Intermolecular strong hydrogen bonds are shown as black dashed lines. Intermolecular weak hydrogen bonds are shown as red dashed lines. Intermolecular C—Cl···N interactions are shown as orange dashed lines. |
C42H56N4O7·CHCl3 | Z = 1 |
Mr = 848.27 | F(000) = 450 |
Triclinic, P1 | Dx = 1.323 Mg m−3 |
Hall symbol: P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.2194 (6) Å | Cell parameters from 9972 reflections |
b = 10.8908 (6) Å | θ = 5.7–52.9° |
c = 11.8698 (7) Å | µ = 0.27 mm−1 |
α = 63.489 (2)° | T = 100 K |
β = 86.467 (2)° | Needle, colourless |
γ = 89.069 (2)° | 0.4 × 0.1 × 0.1 mm |
V = 1064.38 (11) Å3 |
D8 Venture Bruker diffractometer | 8015 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.037 |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | θmax = 26.4°, θmin = 2.8° |
Tmin = 0.908, Tmax = 0.963 | h = −11→11 |
42849 measured reflections | k = −13→13 |
8712 independent reflections | l = −14→14 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.038 | w = 1/[σ2(Fo2) + (0.0306P)2 + 0.6225P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.087 | (Δ/σ)max < 0.001 |
S = 1.08 | Δρmax = 0.30 e Å−3 |
8712 reflections | Δρmin = −0.32 e Å−3 |
518 parameters | Absolute structure: Flack x determined using 3702 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
3 restraints | Absolute structure parameter: 0.006 (18) |
C42H56N4O7·CHCl3 | γ = 89.069 (2)° |
Mr = 848.27 | V = 1064.38 (11) Å3 |
Triclinic, P1 | Z = 1 |
a = 9.2194 (6) Å | Mo Kα radiation |
b = 10.8908 (6) Å | µ = 0.27 mm−1 |
c = 11.8698 (7) Å | T = 100 K |
α = 63.489 (2)° | 0.4 × 0.1 × 0.1 mm |
β = 86.467 (2)° |
D8 Venture Bruker diffractometer | 8712 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | 8015 reflections with I > 2σ(I) |
Tmin = 0.908, Tmax = 0.963 | Rint = 0.037 |
42849 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.087 | Δρmax = 0.30 e Å−3 |
S = 1.08 | Δρmin = −0.32 e Å−3 |
8712 reflections | Absolute structure: Flack x determined using 3702 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
518 parameters | Absolute structure parameter: 0.006 (18) |
3 restraints |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O1 | 1.0678 (2) | 0.1293 (2) | 0.8411 (2) | 0.0231 (5) | |
O2 | 1.1876 (3) | 0.3080 (2) | 0.8461 (2) | 0.0250 (5) | |
O3 | 0.9584 (2) | 0.4011 (2) | 0.4043 (2) | 0.0217 (5) | |
O4 | 0.9878 (3) | 0.1030 (2) | 0.5964 (2) | 0.0291 (6) | |
O6 | 0.6629 (2) | 0.2149 (2) | 0.2316 (2) | 0.0227 (5) | |
O5 | 0.4408 (2) | 0.2042 (2) | 0.4540 (2) | 0.0255 (5) | |
O7 | 0.4784 (3) | 0.3516 (2) | 0.1340 (2) | 0.0258 (5) | |
N1 | 1.1424 (3) | 0.3010 (3) | 0.6606 (2) | 0.0193 (5) | |
H1 | 1.1204 | 0.2444 | 0.6294 | 0.023* | |
N2 | 1.1419 (3) | 0.2721 (3) | 0.3845 (2) | 0.0184 (5) | |
H2 | 1.2365 | 0.2643 | 0.375 | 0.022* | |
N3 | 0.8189 (3) | 0.0590 (3) | 0.4865 (2) | 0.0182 (5) | |
H3N | 0.8047 | 0.0582 | 0.4143 | 0.022* | |
N4 | 0.6448 (3) | 0.3312 (3) | 0.4007 (2) | 0.0201 (6) | |
H4 | 0.7247 | 0.354 | 0.4241 | 0.024* | |
C2 | 1.0641 (4) | 0.0413 (3) | 0.9781 (3) | 0.0247 (7) | |
C3 | 0.9992 (4) | 0.1148 (4) | 1.0520 (3) | 0.0320 (8) | |
H3A | 1.0722 | 0.1771 | 1.0557 | 0.048* | |
H3B | 0.9688 | 0.0472 | 1.1378 | 0.048* | |
H3C | 0.9148 | 0.1676 | 1.0101 | 0.048* | |
C4 | 1.2169 (4) | −0.0068 (4) | 1.0145 (3) | 0.0340 (8) | |
H4A | 1.2551 | −0.0538 | 0.9655 | 0.051* | |
H4B | 1.2152 | −0.0701 | 1.1046 | 0.051* | |
H4C | 1.2793 | 0.0726 | 0.9968 | 0.051* | |
C5 | 0.9658 (5) | −0.0760 (4) | 0.9937 (3) | 0.0337 (8) | |
H5A | 0.8681 | −0.0413 | 0.9694 | 0.051* | |
H5B | 0.9609 | −0.1455 | 1.082 | 0.051* | |
H5C | 1.0048 | −0.1171 | 0.9398 | 0.051* | |
C6 | 1.1374 (3) | 0.2516 (3) | 0.7879 (3) | 0.0188 (6) | |
C7 | 1.1821 (3) | 0.4427 (3) | 0.5718 (3) | 0.0184 (6) | |
C8 | 1.3291 (3) | 0.4874 (3) | 0.5974 (3) | 0.0209 (6) | |
H8A | 1.4024 | 0.416 | 0.6087 | 0.025* | |
H8B | 1.3192 | 0.4987 | 0.6757 | 0.025* | |
C9 | 1.3792 (4) | 0.6251 (3) | 0.4845 (3) | 0.0228 (7) | |
H9A | 1.4202 | 0.6865 | 0.5161 | 0.027* | |
H9B | 1.4557 | 0.6079 | 0.4312 | 0.027* | |
C10 | 1.0661 (4) | 0.5433 (3) | 0.5752 (3) | 0.0212 (7) | |
H10A | 1.0424 | 0.5261 | 0.6636 | 0.025* | |
H10B | 0.9763 | 0.5293 | 0.5405 | 0.025* | |
C11 | 1.1215 (4) | 0.6921 (3) | 0.4972 (3) | 0.0250 (7) | |
H11A | 1.1538 | 0.7293 | 0.554 | 0.03* | |
H11B | 1.0423 | 0.7503 | 0.4483 | 0.03* | |
C12 | 1.2495 (4) | 0.6932 (3) | 0.4068 (3) | 0.0229 (7) | |
H12 | 1.2749 | 0.7893 | 0.3434 | 0.027* | |
C13 | 1.2037 (4) | 0.6084 (3) | 0.3410 (3) | 0.0209 (6) | |
H13A | 1.273 | 0.6244 | 0.2685 | 0.025* | |
H13B | 1.1059 | 0.6362 | 0.3088 | 0.025* | |
C14 | 1.2014 (3) | 0.4545 (3) | 0.4365 (3) | 0.0180 (6) | |
H14 | 1.2989 | 0.4167 | 0.4283 | 0.022* | |
C15 | 1.0890 (3) | 0.3744 (3) | 0.4071 (3) | 0.0168 (6) | |
C16 | 1.0454 (3) | 0.1744 (3) | 0.3755 (3) | 0.0196 (6) | |
H16 | 0.9842 | 0.2224 | 0.3018 | 0.024* | |
C17 | 1.1352 (4) | 0.0646 (3) | 0.3577 (3) | 0.0259 (7) | |
H17A | 1.0701 | −0.002 | 0.3515 | 0.039* | |
H17B | 1.1951 | 0.0176 | 0.4301 | 0.039* | |
H17C | 1.1982 | 0.1078 | 0.2803 | 0.039* | |
C18 | 0.9468 (3) | 0.1090 (3) | 0.4981 (3) | 0.0197 (6) | |
C19 | 0.7011 (3) | 0.0056 (3) | 0.5867 (3) | 0.0201 (6) | |
C20 | 0.7585 (4) | −0.0962 (4) | 0.7133 (3) | 0.0283 (8) | |
H20A | 0.8161 | −0.1678 | 0.7019 | 0.034* | |
H20B | 0.8229 | −0.0474 | 0.7443 | 0.034* | |
C21 | 0.6307 (4) | −0.1633 (4) | 0.8104 (3) | 0.0329 (8) | |
H21A | 0.6228 | −0.2616 | 0.8305 | 0.04* | |
H21B | 0.6476 | −0.157 | 0.8892 | 0.04* | |
C22 | 0.4899 (4) | −0.0907 (4) | 0.7570 (3) | 0.0291 (8) | |
H22 | 0.4081 | −0.1283 | 0.8229 | 0.035* | |
C23 | 0.5919 (3) | −0.0714 (3) | 0.5489 (3) | 0.0215 (7) | |
H23A | 0.6379 | −0.1539 | 0.5483 | 0.026* | |
H23B | 0.5616 | −0.0117 | 0.4629 | 0.026* | |
C24 | 0.4578 (4) | −0.1144 (4) | 0.6431 (3) | 0.0251 (7) | |
H24A | 0.3729 | −0.0596 | 0.6017 | 0.03* | |
H24B | 0.4344 | −0.2125 | 0.6711 | 0.03* | |
C25 | 0.5078 (4) | 0.0630 (4) | 0.7147 (3) | 0.0293 (8) | |
H25A | 0.5363 | 0.0786 | 0.7864 | 0.035* | |
H25B | 0.4141 | 0.1091 | 0.6871 | 0.035* | |
C26 | 0.6258 (4) | 0.1254 (3) | 0.6041 (3) | 0.0208 (7) | |
H26 | 0.6998 | 0.1757 | 0.6264 | 0.025* | |
C27 | 0.5618 (3) | 0.2238 (3) | 0.4817 (3) | 0.0199 (7) | |
C28 | 0.5981 (3) | 0.4082 (3) | 0.2734 (3) | 0.0184 (6) | |
H28 | 0.4997 | 0.4461 | 0.2785 | 0.022* | |
C29 | 0.7008 (3) | 0.5276 (3) | 0.1918 (3) | 0.0201 (6) | |
H29A | 0.8023 | 0.4964 | 0.2074 | 0.024* | |
H29B | 0.6859 | 0.5548 | 0.1019 | 0.024* | |
C30 | 0.6795 (3) | 0.6509 (3) | 0.2164 (3) | 0.0184 (6) | |
C31 | 0.7622 (3) | 0.6728 (3) | 0.3003 (3) | 0.0215 (7) | |
H31 | 0.8332 | 0.6077 | 0.3449 | 0.026* | |
C32 | 0.7416 (4) | 0.7892 (3) | 0.3191 (3) | 0.0234 (7) | |
H32 | 0.7984 | 0.8032 | 0.3766 | 0.028* | |
C33 | 0.6387 (4) | 0.8849 (3) | 0.2545 (3) | 0.0241 (7) | |
H33 | 0.6258 | 0.9652 | 0.2663 | 0.029* | |
C34 | 0.5550 (4) | 0.8624 (3) | 0.1729 (3) | 0.0232 (7) | |
H34 | 0.4832 | 0.927 | 0.1293 | 0.028* | |
C35 | 0.5748 (4) | 0.7466 (3) | 0.1541 (3) | 0.0215 (7) | |
H35 | 0.5161 | 0.7323 | 0.0978 | 0.026* | |
C36 | 0.5859 (3) | 0.3116 (3) | 0.2127 (3) | 0.0210 (7) | |
C37 | 0.4548 (4) | 0.2729 (3) | 0.0647 (3) | 0.0239 (7) | |
H37A | 0.3512 | 0.2783 | 0.0456 | 0.029* | |
H37B | 0.4769 | 0.1753 | 0.1182 | 0.029* | |
C38 | 0.5472 (4) | 0.3240 (4) | −0.0556 (3) | 0.0245 (7) | |
C39 | 0.5375 (4) | 0.4594 (4) | −0.1454 (4) | 0.0319 (8) | |
H39 | 0.4758 | 0.5207 | −0.1284 | 0.038* | |
C40 | 0.6175 (5) | 0.5056 (5) | −0.2598 (4) | 0.0459 (11) | |
H40 | 0.6111 | 0.5985 | −0.3209 | 0.055* | |
C41 | 0.7064 (4) | 0.4168 (5) | −0.2849 (4) | 0.0455 (12) | |
H41 | 0.7596 | 0.4482 | −0.3641 | 0.055* | |
C42 | 0.7187 (4) | 0.2817 (5) | −0.1953 (4) | 0.0383 (9) | |
H42 | 0.781 | 0.2209 | −0.2123 | 0.046* | |
C43 | 0.6393 (4) | 0.2362 (4) | −0.0806 (3) | 0.0284 (8) | |
H43 | 0.6482 | 0.144 | −0.0186 | 0.034* | |
C1' | 1.0834 (4) | 0.5291 (4) | 0.9249 (3) | 0.0258 (7) | |
H1' | 1.132 | 0.4645 | 0.8961 | 0.031* | |
Cl1' | 0.89599 (9) | 0.52131 (11) | 0.91218 (9) | 0.0383 (2) | |
Cl2' | 1.12316 (10) | 0.47771 (11) | 1.08293 (9) | 0.0413 (2) | |
Cl3' | 1.15106 (13) | 0.69484 (11) | 0.82768 (10) | 0.0495 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0315 (13) | 0.0226 (12) | 0.0123 (11) | −0.0053 (10) | −0.0028 (9) | −0.0049 (9) |
O2 | 0.0315 (13) | 0.0266 (12) | 0.0178 (11) | −0.0034 (10) | −0.0019 (9) | −0.0107 (10) |
O3 | 0.0192 (12) | 0.0247 (12) | 0.0221 (12) | 0.0005 (9) | −0.0045 (9) | −0.0107 (10) |
O4 | 0.0364 (14) | 0.0320 (13) | 0.0152 (11) | −0.0141 (11) | −0.0039 (10) | −0.0065 (10) |
O6 | 0.0273 (12) | 0.0230 (12) | 0.0203 (11) | 0.0059 (10) | −0.0049 (9) | −0.0117 (9) |
O5 | 0.0175 (11) | 0.0283 (12) | 0.0307 (13) | −0.0003 (9) | −0.0002 (9) | −0.0134 (10) |
O7 | 0.0270 (12) | 0.0291 (13) | 0.0284 (13) | 0.0060 (10) | −0.0111 (10) | −0.0183 (11) |
N1 | 0.0228 (14) | 0.0205 (13) | 0.0144 (13) | −0.0030 (11) | −0.0014 (10) | −0.0076 (11) |
N2 | 0.0145 (12) | 0.0208 (13) | 0.0193 (13) | −0.0031 (10) | 0.0017 (10) | −0.0085 (11) |
N3 | 0.0204 (13) | 0.0207 (13) | 0.0124 (12) | −0.0024 (11) | −0.0011 (10) | −0.0064 (11) |
N4 | 0.0206 (14) | 0.0229 (14) | 0.0185 (13) | −0.0018 (11) | −0.0017 (10) | −0.0105 (11) |
C2 | 0.0307 (18) | 0.0261 (18) | 0.0108 (15) | −0.0006 (14) | −0.0026 (13) | −0.0022 (13) |
C3 | 0.033 (2) | 0.043 (2) | 0.0204 (17) | −0.0050 (17) | 0.0013 (15) | −0.0156 (16) |
C4 | 0.036 (2) | 0.034 (2) | 0.0256 (19) | 0.0067 (16) | −0.0073 (15) | −0.0063 (16) |
C5 | 0.045 (2) | 0.0283 (19) | 0.0205 (18) | −0.0120 (16) | 0.0028 (16) | −0.0042 (15) |
C6 | 0.0206 (15) | 0.0198 (15) | 0.0149 (14) | −0.0002 (12) | −0.0006 (12) | −0.0069 (12) |
C7 | 0.0208 (16) | 0.0194 (15) | 0.0153 (15) | −0.0035 (12) | 0.0003 (12) | −0.0081 (12) |
C8 | 0.0216 (16) | 0.0232 (17) | 0.0173 (15) | −0.0031 (13) | −0.0017 (12) | −0.0083 (13) |
C9 | 0.0219 (16) | 0.0243 (17) | 0.0225 (17) | −0.0079 (13) | 0.0009 (13) | −0.0107 (14) |
C10 | 0.0216 (16) | 0.0236 (17) | 0.0188 (16) | 0.0002 (13) | 0.0024 (13) | −0.0103 (14) |
C11 | 0.0296 (18) | 0.0217 (17) | 0.0235 (17) | −0.0009 (14) | 0.0018 (14) | −0.0103 (14) |
C12 | 0.0258 (17) | 0.0193 (16) | 0.0216 (16) | −0.0055 (13) | 0.0003 (13) | −0.0075 (13) |
C13 | 0.0227 (16) | 0.0205 (16) | 0.0159 (15) | −0.0059 (13) | 0.0009 (12) | −0.0049 (13) |
C14 | 0.0161 (15) | 0.0211 (15) | 0.0161 (15) | −0.0010 (12) | 0.0002 (12) | −0.0078 (13) |
C15 | 0.0185 (15) | 0.0184 (15) | 0.0096 (13) | −0.0018 (12) | −0.0005 (11) | −0.0028 (12) |
C16 | 0.0183 (15) | 0.0200 (16) | 0.0213 (16) | −0.0020 (12) | −0.0027 (12) | −0.0097 (13) |
C17 | 0.0273 (18) | 0.0232 (17) | 0.0287 (18) | 0.0008 (14) | 0.0001 (14) | −0.0132 (15) |
C18 | 0.0242 (16) | 0.0149 (15) | 0.0183 (15) | −0.0009 (12) | −0.0027 (13) | −0.0057 (12) |
C19 | 0.0224 (16) | 0.0203 (16) | 0.0153 (15) | −0.0048 (12) | 0.0004 (12) | −0.0060 (13) |
C20 | 0.036 (2) | 0.0286 (18) | 0.0153 (16) | −0.0058 (15) | −0.0033 (14) | −0.0054 (14) |
C21 | 0.044 (2) | 0.033 (2) | 0.0163 (17) | −0.0165 (17) | 0.0027 (15) | −0.0052 (15) |
C22 | 0.0334 (19) | 0.035 (2) | 0.0195 (17) | −0.0143 (16) | 0.0082 (14) | −0.0134 (15) |
C23 | 0.0250 (17) | 0.0222 (16) | 0.0181 (16) | −0.0039 (13) | −0.0003 (13) | −0.0095 (13) |
C24 | 0.0272 (17) | 0.0287 (18) | 0.0207 (16) | −0.0105 (14) | 0.0048 (14) | −0.0126 (14) |
C25 | 0.037 (2) | 0.036 (2) | 0.0196 (17) | −0.0117 (16) | 0.0106 (14) | −0.0177 (15) |
C26 | 0.0248 (16) | 0.0233 (16) | 0.0167 (15) | −0.0053 (13) | 0.0028 (12) | −0.0116 (13) |
C27 | 0.0179 (16) | 0.0224 (16) | 0.0244 (16) | −0.0025 (13) | 0.0035 (13) | −0.0155 (14) |
C28 | 0.0189 (15) | 0.0212 (16) | 0.0179 (15) | 0.0026 (12) | −0.0040 (12) | −0.0110 (13) |
C29 | 0.0196 (16) | 0.0223 (16) | 0.0186 (15) | 0.0004 (13) | 0.0003 (12) | −0.0095 (13) |
C30 | 0.0200 (15) | 0.0181 (15) | 0.0150 (14) | −0.0017 (12) | 0.0050 (12) | −0.0060 (12) |
C31 | 0.0211 (16) | 0.0214 (16) | 0.0193 (16) | 0.0001 (13) | 0.0015 (12) | −0.0072 (13) |
C32 | 0.0238 (17) | 0.0259 (17) | 0.0237 (17) | −0.0005 (13) | −0.0011 (13) | −0.0139 (14) |
C33 | 0.0279 (17) | 0.0187 (16) | 0.0265 (17) | −0.0018 (13) | 0.0046 (14) | −0.0116 (14) |
C34 | 0.0229 (16) | 0.0182 (16) | 0.0238 (17) | 0.0028 (13) | 0.0011 (13) | −0.0054 (13) |
C35 | 0.0221 (16) | 0.0233 (16) | 0.0168 (15) | −0.0017 (13) | 0.0016 (13) | −0.0073 (13) |
C36 | 0.0208 (16) | 0.0229 (17) | 0.0197 (16) | −0.0012 (13) | −0.0019 (13) | −0.0097 (13) |
C37 | 0.0280 (18) | 0.0236 (17) | 0.0233 (17) | −0.0008 (14) | −0.0059 (14) | −0.0126 (14) |
C38 | 0.0238 (17) | 0.0284 (17) | 0.0238 (17) | −0.0042 (14) | −0.0102 (14) | −0.0128 (15) |
C39 | 0.0273 (19) | 0.0280 (19) | 0.034 (2) | −0.0013 (15) | −0.0129 (15) | −0.0069 (16) |
C40 | 0.036 (2) | 0.045 (2) | 0.035 (2) | −0.0161 (19) | −0.0136 (18) | 0.0036 (19) |
C41 | 0.027 (2) | 0.075 (3) | 0.027 (2) | −0.023 (2) | −0.0011 (16) | −0.015 (2) |
C42 | 0.028 (2) | 0.061 (3) | 0.037 (2) | −0.0103 (18) | −0.0017 (16) | −0.031 (2) |
C43 | 0.0280 (18) | 0.0317 (19) | 0.0279 (18) | −0.0047 (15) | −0.0034 (14) | −0.0150 (15) |
C1' | 0.0252 (17) | 0.0344 (19) | 0.0222 (16) | −0.0014 (14) | 0.0004 (13) | −0.0165 (15) |
Cl1' | 0.0243 (4) | 0.0616 (6) | 0.0342 (5) | −0.0032 (4) | −0.0015 (4) | −0.0259 (5) |
Cl2' | 0.0409 (5) | 0.0598 (6) | 0.0259 (5) | 0.0046 (5) | −0.0090 (4) | −0.0208 (5) |
Cl3' | 0.0607 (7) | 0.0457 (6) | 0.0387 (6) | −0.0254 (5) | 0.0144 (5) | −0.0172 (5) |
O1—C6 | 1.346 (4) | C17—H17B | 0.98 |
O1—C2 | 1.472 (4) | C17—H17C | 0.98 |
O2—C6 | 1.222 (4) | C19—C23 | 1.529 (4) |
O3—C15 | 1.233 (4) | C19—C20 | 1.536 (4) |
O4—C18 | 1.221 (4) | C19—C26 | 1.556 (4) |
O6—C36 | 1.203 (4) | C20—C21 | 1.536 (5) |
O5—C27 | 1.231 (4) | C20—H20A | 0.99 |
O7—C36 | 1.334 (4) | C20—H20B | 0.99 |
O7—C37 | 1.454 (4) | C21—C22 | 1.527 (6) |
N1—C6 | 1.357 (4) | C21—H21A | 0.99 |
N1—C7 | 1.465 (4) | C21—H21B | 0.99 |
N1—H1 | 0.88 | C22—C25 | 1.527 (5) |
N2—C15 | 1.336 (4) | C22—C24 | 1.531 (5) |
N2—C16 | 1.442 (4) | C22—H22 | 1 |
N2—H2 | 0.88 | C23—C24 | 1.542 (4) |
N3—C18 | 1.346 (4) | C23—H23A | 0.99 |
N3—C19 | 1.475 (4) | C23—H23B | 0.99 |
N3—H3N | 0.88 | C24—H24A | 0.99 |
N4—C27 | 1.347 (4) | C24—H24B | 0.99 |
N4—C28 | 1.452 (4) | C25—C26 | 1.556 (4) |
N4—H4 | 0.88 | C25—H25A | 0.99 |
C2—C5 | 1.514 (5) | C25—H25B | 0.99 |
C2—C4 | 1.515 (5) | C26—C27 | 1.517 (5) |
C2—C3 | 1.521 (5) | C26—H26 | 1 |
C3—H3A | 0.98 | C28—C29 | 1.526 (4) |
C3—H3B | 0.98 | C28—C36 | 1.527 (4) |
C3—H3C | 0.98 | C28—H28 | 1 |
C4—H4A | 0.98 | C29—C30 | 1.503 (4) |
C4—H4B | 0.98 | C29—H29A | 0.99 |
C4—H4C | 0.98 | C29—H29B | 0.99 |
C5—H5A | 0.98 | C30—C35 | 1.391 (5) |
C5—H5B | 0.98 | C30—C31 | 1.393 (5) |
C5—H5C | 0.98 | C31—C32 | 1.391 (5) |
C7—C10 | 1.530 (4) | C31—H31 | 0.95 |
C7—C8 | 1.539 (4) | C32—C33 | 1.385 (5) |
C7—C14 | 1.552 (4) | C32—H32 | 0.95 |
C8—C9 | 1.553 (4) | C33—C34 | 1.380 (5) |
C8—H8A | 0.99 | C33—H33 | 0.95 |
C8—H8B | 0.99 | C34—C35 | 1.383 (5) |
C9—C12 | 1.525 (5) | C34—H34 | 0.95 |
C9—H9A | 0.99 | C35—H35 | 0.95 |
C9—H9B | 0.99 | C37—C38 | 1.494 (5) |
C10—C11 | 1.540 (4) | C37—H37A | 0.99 |
C10—H10A | 0.99 | C37—H37B | 0.99 |
C10—H10B | 0.99 | C38—C43 | 1.385 (5) |
C11—C12 | 1.542 (5) | C38—C39 | 1.387 (5) |
C11—H11A | 0.99 | C39—C40 | 1.386 (6) |
C11—H11B | 0.99 | C39—H39 | 0.95 |
C12—C13 | 1.529 (5) | C40—C41 | 1.378 (7) |
C12—H12 | 1 | C40—H40 | 0.95 |
C13—C14 | 1.548 (4) | C41—C42 | 1.386 (6) |
C13—H13A | 0.99 | C41—H41 | 0.95 |
C13—H13B | 0.99 | C42—C43 | 1.385 (5) |
C14—C15 | 1.518 (4) | C42—H42 | 0.95 |
C14—H14 | 1 | C43—H43 | 0.95 |
C16—C17 | 1.526 (4) | C1'—Cl3' | 1.751 (4) |
C16—C18 | 1.545 (4) | C1'—Cl1' | 1.751 (3) |
C16—H16 | 1 | C1'—Cl2' | 1.762 (3) |
C17—H17A | 0.98 | C1'—H1' | 1 |
C6—O1—C2 | 121.4 (2) | C23—C19—C26 | 110.5 (3) |
C36—O7—C37 | 117.1 (3) | C20—C19—C26 | 108.6 (3) |
C6—N1—C7 | 124.1 (3) | C21—C20—C19 | 109.8 (3) |
C6—N1—H1 | 118 | C21—C20—H20A | 109.7 |
C7—N1—H1 | 118 | C19—C20—H20A | 109.7 |
C15—N2—C16 | 120.6 (3) | C21—C20—H20B | 109.7 |
C15—N2—H2 | 119.7 | C19—C20—H20B | 109.7 |
C16—N2—H2 | 119.7 | H20A—C20—H20B | 108.2 |
C18—N3—C19 | 124.5 (3) | C22—C21—C20 | 109.6 (3) |
C18—N3—H3N | 117.8 | C22—C21—H21A | 109.7 |
C19—N3—H3N | 117.8 | C20—C21—H21A | 109.7 |
C27—N4—C28 | 117.8 (3) | C22—C21—H21B | 109.7 |
C27—N4—H4 | 121.1 | C20—C21—H21B | 109.7 |
C28—N4—H4 | 121.1 | H21A—C21—H21B | 108.2 |
O1—C2—C5 | 102.2 (3) | C25—C22—C21 | 109.5 (3) |
O1—C2—C4 | 108.5 (3) | C25—C22—C24 | 109.2 (3) |
C5—C2—C4 | 111.6 (3) | C21—C22—C24 | 108.9 (3) |
O1—C2—C3 | 111.8 (3) | C25—C22—H22 | 109.8 |
C5—C2—C3 | 110.5 (3) | C21—C22—H22 | 109.8 |
C4—C2—C3 | 111.7 (3) | C24—C22—H22 | 109.8 |
C2—C3—H3A | 109.5 | C19—C23—C24 | 109.9 (3) |
C2—C3—H3B | 109.5 | C19—C23—H23A | 109.7 |
H3A—C3—H3B | 109.5 | C24—C23—H23A | 109.7 |
C2—C3—H3C | 109.5 | C19—C23—H23B | 109.7 |
H3A—C3—H3C | 109.5 | C24—C23—H23B | 109.7 |
H3B—C3—H3C | 109.5 | H23A—C23—H23B | 108.2 |
C2—C4—H4A | 109.5 | C22—C24—C23 | 109.3 (3) |
C2—C4—H4B | 109.5 | C22—C24—H24A | 109.8 |
H4A—C4—H4B | 109.5 | C23—C24—H24A | 109.8 |
C2—C4—H4C | 109.5 | C22—C24—H24B | 109.8 |
H4A—C4—H4C | 109.5 | C23—C24—H24B | 109.8 |
H4B—C4—H4C | 109.5 | H24A—C24—H24B | 108.3 |
C2—C5—H5A | 109.5 | C22—C25—C26 | 110.4 (3) |
C2—C5—H5B | 109.5 | C22—C25—H25A | 109.6 |
H5A—C5—H5B | 109.5 | C26—C25—H25A | 109.6 |
C2—C5—H5C | 109.5 | C22—C25—H25B | 109.6 |
H5A—C5—H5C | 109.5 | C26—C25—H25B | 109.6 |
H5B—C5—H5C | 109.5 | H25A—C25—H25B | 108.1 |
O2—C6—O1 | 125.0 (3) | C27—C26—C25 | 112.1 (3) |
O2—C6—N1 | 126.0 (3) | C27—C26—C19 | 109.6 (2) |
O1—C6—N1 | 109.0 (3) | C25—C26—C19 | 108.2 (3) |
N1—C7—C10 | 111.5 (2) | C27—C26—H26 | 109 |
N1—C7—C8 | 112.5 (2) | C25—C26—H26 | 109 |
C10—C7—C8 | 108.5 (3) | C19—C26—H26 | 109 |
N1—C7—C14 | 109.2 (2) | O5—C27—N4 | 120.5 (3) |
C10—C7—C14 | 109.5 (2) | O5—C27—C26 | 121.8 (3) |
C8—C7—C14 | 105.5 (2) | N4—C27—C26 | 117.7 (3) |
C7—C8—C9 | 109.4 (3) | N4—C28—C29 | 112.5 (2) |
C7—C8—H8A | 109.8 | N4—C28—C36 | 109.2 (2) |
C9—C8—H8A | 109.8 | C29—C28—C36 | 109.9 (3) |
C7—C8—H8B | 109.8 | N4—C28—H28 | 108.4 |
C9—C8—H8B | 109.8 | C29—C28—H28 | 108.4 |
H8A—C8—H8B | 108.2 | C36—C28—H28 | 108.4 |
C12—C9—C8 | 109.3 (3) | C30—C29—C28 | 113.4 (3) |
C12—C9—H9A | 109.8 | C30—C29—H29A | 108.9 |
C8—C9—H9A | 109.8 | C28—C29—H29A | 108.9 |
C12—C9—H9B | 109.8 | C30—C29—H29B | 108.9 |
C8—C9—H9B | 109.8 | C28—C29—H29B | 108.9 |
H9A—C9—H9B | 108.3 | H29A—C29—H29B | 107.7 |
C7—C10—C11 | 110.1 (3) | C35—C30—C31 | 118.5 (3) |
C7—C10—H10A | 109.6 | C35—C30—C29 | 119.6 (3) |
C11—C10—H10A | 109.6 | C31—C30—C29 | 121.9 (3) |
C7—C10—H10B | 109.6 | C32—C31—C30 | 120.4 (3) |
C11—C10—H10B | 109.6 | C32—C31—H31 | 119.8 |
H10A—C10—H10B | 108.2 | C30—C31—H31 | 119.8 |
C10—C11—C12 | 108.8 (3) | C33—C32—C31 | 120.4 (3) |
C10—C11—H11A | 109.9 | C33—C32—H32 | 119.8 |
C12—C11—H11A | 109.9 | C31—C32—H32 | 119.8 |
C10—C11—H11B | 109.9 | C34—C33—C32 | 119.4 (3) |
C12—C11—H11B | 109.9 | C34—C33—H33 | 120.3 |
H11A—C11—H11B | 108.3 | C32—C33—H33 | 120.3 |
C9—C12—C13 | 108.9 (3) | C33—C34—C35 | 120.5 (3) |
C9—C12—C11 | 108.5 (3) | C33—C34—H34 | 119.7 |
C13—C12—C11 | 107.8 (3) | C35—C34—H34 | 119.7 |
C9—C12—H12 | 110.5 | C34—C35—C30 | 120.8 (3) |
C13—C12—H12 | 110.5 | C34—C35—H35 | 119.6 |
C11—C12—H12 | 110.5 | C30—C35—H35 | 119.6 |
C12—C13—C14 | 109.0 (3) | O6—C36—O7 | 125.0 (3) |
C12—C13—H13A | 109.9 | O6—C36—C28 | 125.1 (3) |
C14—C13—H13A | 109.9 | O7—C36—C28 | 109.9 (3) |
C12—C13—H13B | 109.9 | O7—C37—C38 | 112.1 (3) |
C14—C13—H13B | 109.9 | O7—C37—H37A | 109.2 |
H13A—C13—H13B | 108.3 | C38—C37—H37A | 109.2 |
C15—C14—C13 | 111.6 (3) | O7—C37—H37B | 109.2 |
C15—C14—C7 | 114.1 (2) | C38—C37—H37B | 109.2 |
C13—C14—C7 | 108.5 (2) | H37A—C37—H37B | 107.9 |
C15—C14—H14 | 107.4 | C43—C38—C39 | 119.4 (3) |
C13—C14—H14 | 107.4 | C43—C38—C37 | 120.7 (3) |
C7—C14—H14 | 107.4 | C39—C38—C37 | 119.9 (3) |
O3—C15—N2 | 122.2 (3) | C40—C39—C38 | 120.1 (4) |
O3—C15—C14 | 122.8 (3) | C40—C39—H39 | 119.9 |
N2—C15—C14 | 115.0 (3) | C38—C39—H39 | 119.9 |
N2—C16—C17 | 109.2 (3) | C41—C40—C39 | 120.0 (4) |
N2—C16—C18 | 108.5 (2) | C41—C40—H40 | 120 |
C17—C16—C18 | 110.5 (3) | C39—C40—H40 | 120 |
N2—C16—H16 | 109.6 | C40—C41—C42 | 120.3 (4) |
C17—C16—H16 | 109.6 | C40—C41—H41 | 119.8 |
C18—C16—H16 | 109.6 | C42—C41—H41 | 119.8 |
C16—C17—H17A | 109.5 | C43—C42—C41 | 119.4 (4) |
C16—C17—H17B | 109.5 | C43—C42—H42 | 120.3 |
H17A—C17—H17B | 109.5 | C41—C42—H42 | 120.3 |
C16—C17—H17C | 109.5 | C42—C43—C38 | 120.6 (4) |
H17A—C17—H17C | 109.5 | C42—C43—H43 | 119.7 |
H17B—C17—H17C | 109.5 | C38—C43—H43 | 119.7 |
O4—C18—N3 | 124.9 (3) | Cl3'—C1'—Cl1' | 110.4 (2) |
O4—C18—C16 | 120.3 (3) | Cl3'—C1'—Cl2' | 110.83 (19) |
N3—C18—C16 | 114.8 (3) | Cl1'—C1'—Cl2' | 110.70 (19) |
N3—C19—C23 | 108.1 (2) | Cl3'—C1'—H1' | 108.3 |
N3—C19—C20 | 111.5 (3) | Cl1'—C1'—H1' | 108.3 |
C23—C19—C20 | 107.7 (3) | Cl2'—C1'—H1' | 108.3 |
N3—C19—C26 | 110.3 (2) | ||
C2—O1—C6—N1 | 171.0 (3) | N3—C19—C20—C21 | −172.7 (3) |
C6—N1—C7—C14 | 170.3 (3) | C23—C19—C20—C21 | −54.2 (4) |
N1—C7—C14—C15 | 40.5 (3) | C26—C19—C20—C21 | 65.5 (3) |
C7—C14—C15—N2 | −115.8 (3) | C19—C20—C21—C22 | −9.3 (4) |
C14—C15—N2—C16 | 169.9 (3) | C20—C21—C22—C25 | −54.1 (4) |
C15—N2—C16—C18 | −56.0 (4) | C20—C21—C22—C24 | 65.1 (4) |
N2—C16—C18—N3 | 155.4 (3) | N3—C19—C23—C24 | −173.3 (3) |
C16—C18—N3—C19 | −173.2 (3) | C20—C19—C23—C24 | 66.0 (3) |
C18—N3—C19—C26 | 72.4 (4) | C26—C19—C23—C24 | −52.5 (3) |
N3—C19—C26—C27 | 60.2 (3) | C25—C22—C24—C23 | 66.2 (4) |
C19—C26—C27—N4 | −92.4 (3) | C21—C22—C24—C23 | −53.3 (4) |
C26—C27—N4—C28 | 167.0 (3) | C19—C23—C24—C22 | −10.8 (4) |
C27—N4—C28—C36 | −58.1 (4) | C21—C22—C25—C26 | 64.3 (4) |
N4—C28—C36—O7 | 147.0 (3) | C24—C22—C25—C26 | −54.8 (4) |
C6—O1—C2—C5 | 175.6 (3) | C22—C25—C26—C27 | 113.0 (3) |
C6—O1—C2—C4 | −66.3 (4) | C22—C25—C26—C19 | −7.9 (4) |
C6—O1—C2—C3 | 57.3 (4) | C23—C19—C26—C27 | −59.3 (3) |
C2—O1—C6—O2 | −9.0 (5) | C20—C19—C26—C27 | −177.3 (3) |
C7—N1—C6—O2 | −13.3 (5) | N3—C19—C26—C25 | −177.4 (3) |
C7—N1—C6—O1 | 166.7 (3) | C23—C19—C26—C25 | 63.2 (3) |
C6—N1—C7—C10 | −68.6 (4) | C20—C19—C26—C25 | −54.8 (3) |
C6—N1—C7—C8 | 53.5 (4) | C28—N4—C27—O5 | −10.1 (4) |
N1—C7—C8—C9 | 168.0 (2) | C25—C26—C27—O5 | −35.5 (4) |
C10—C7—C8—C9 | −68.2 (3) | C19—C26—C27—O5 | 84.6 (4) |
C14—C7—C8—C9 | 49.1 (3) | C25—C26—C27—N4 | 147.5 (3) |
C7—C8—C9—C12 | 17.7 (4) | C27—N4—C28—C29 | 179.6 (3) |
N1—C7—C10—C11 | 171.1 (3) | N4—C28—C29—C30 | −78.8 (3) |
C8—C7—C10—C11 | 46.7 (3) | C36—C28—C29—C30 | 159.3 (3) |
C14—C7—C10—C11 | −68.0 (3) | C28—C29—C30—C35 | −85.7 (4) |
C7—C10—C11—C12 | 18.9 (4) | C28—C29—C30—C31 | 94.4 (3) |
C8—C9—C12—C13 | −68.8 (3) | C35—C30—C31—C32 | −1.1 (5) |
C8—C9—C12—C11 | 48.2 (3) | C29—C30—C31—C32 | 178.8 (3) |
C10—C11—C12—C9 | −69.9 (3) | C30—C31—C32—C33 | −0.1 (5) |
C10—C11—C12—C13 | 47.9 (4) | C31—C32—C33—C34 | 1.1 (5) |
C9—C12—C13—C14 | 44.8 (3) | C32—C33—C34—C35 | −0.9 (5) |
C11—C12—C13—C14 | −72.7 (3) | C33—C34—C35—C30 | −0.3 (5) |
C12—C13—C14—C15 | 150.0 (3) | C31—C30—C35—C34 | 1.3 (5) |
C12—C13—C14—C7 | 23.4 (3) | C29—C30—C35—C34 | −178.6 (3) |
C10—C7—C14—C15 | −81.8 (3) | C37—O7—C36—O6 | −1.0 (5) |
C8—C7—C14—C15 | 161.6 (3) | C37—O7—C36—C28 | 178.1 (3) |
N1—C7—C14—C13 | 165.6 (2) | N4—C28—C36—O6 | −33.9 (4) |
C10—C7—C14—C13 | 43.3 (3) | C29—C28—C36—O6 | 90.0 (4) |
C8—C7—C14—C13 | −73.3 (3) | C29—C28—C36—O7 | −89.1 (3) |
C16—N2—C15—O3 | −10.0 (4) | C36—O7—C37—C38 | −87.1 (3) |
C13—C14—C15—O3 | −59.4 (4) | O7—C37—C38—C43 | 124.5 (3) |
C7—C14—C15—O3 | 64.1 (4) | O7—C37—C38—C39 | −57.7 (4) |
C13—C14—C15—N2 | 120.7 (3) | C43—C38—C39—C40 | 1.1 (5) |
C15—N2—C16—C17 | −176.4 (3) | C37—C38—C39—C40 | −176.7 (3) |
C19—N3—C18—O4 | 8.4 (5) | C38—C39—C40—C41 | 0.3 (6) |
N2—C16—C18—O4 | −26.1 (4) | C39—C40—C41—C42 | −1.3 (6) |
C17—C16—C18—O4 | 93.5 (4) | C40—C41—C42—C43 | 0.8 (6) |
C17—C16—C18—N3 | −85.0 (3) | C41—C42—C43—C38 | 0.6 (5) |
C18—N3—C19—C23 | −166.8 (3) | C39—C38—C43—C42 | −1.6 (5) |
C18—N3—C19—C20 | −48.5 (4) | C37—C38—C43—C42 | 176.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O4 | 0.88 | 2.16 | 2.994 (4) | 157 |
N2—H2···O5i | 0.88 | 2.12 | 2.914 (3) | 150 |
N3—H3N···O6 | 0.88 | 2.51 | 3.159 (3) | 131 |
N4—H4···O3 | 0.88 | 2.20 | 3.009 (3) | 153 |
C1′—H1′···O2 | 1.00 | 2.09 | 3.071 (4) | 167 |
Symmetry code: (i) x+1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O4 | 0.88 | 2.16 | 2.994 (4) | 157 |
N2—H2···O5i | 0.88 | 2.12 | 2.914 (3) | 150 |
N3—H3N···O6 | 0.88 | 2.51 | 3.159 (3) | 131 |
N4—H4···O3 | 0.88 | 2.20 | 3.009 (3) | 153 |
C1'—H1'···O2 | 1.00 | 2.09 | 3.071 (4) | 167 |
Symmetry code: (i) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C42H56N4O7·CHCl3 |
Mr | 848.27 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 9.2194 (6), 10.8908 (6), 11.8698 (7) |
α, β, γ (°) | 63.489 (2), 86.467 (2), 89.069 (2) |
V (Å3) | 1064.38 (11) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.27 |
Crystal size (mm) | 0.4 × 0.1 × 0.1 |
Data collection | |
Diffractometer | D8 Venture Bruker diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2014) |
Tmin, Tmax | 0.908, 0.963 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 42849, 8712, 8015 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.087, 1.08 |
No. of reflections | 8712 |
No. of parameters | 518 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.32 |
Absolute structure | Flack x determined using 3702 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Absolute structure parameter | 0.006 (18) |
Computer programs: APEX2 (Bruker, 2014), SAINT (Bruker, 2014), SIR2008 (Burla et al., 2007), SHELXL2014 (Sheldrick, 2015), Mercury (Macrae et al., 2008) and pyMOL (DeLano, 2002), WinGX (Farrugia, 2012) and enCIFer (Allen et al., 2004).
Acknowledgements
The Plateforme de mesures de diffraction X of the Université de Lorraine is thanked for providing access to crystallographic facilities.
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