research communications
N-{N-[N-(tert-butoxycarbonyl)-L-α-aspartyl]-L-α-aspartyl}-L-α-aspartic acid 14,24,34-trimethyl ester 31-2-oxo-2-phenylethyl ester {Boc-[Asp(OMe)]3-OPac}
ofaOsaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan
*Correspondence e-mail: t.kato@gly.oups.ac.jp
In the title homotripeptide {Boc-[Asp(OMe)]3-OPac}, C28H37N3O13, all peptide bonds adopt an s-trans conformation with respect to the N—H and C=O groups. In the crystal, N—H⋯O hydrogen bonds result in an infinite parallel β-sheet structure running along the b-axis direction. The Boc protecting group at the N-terminus of the peptide is disordered over two sites with occupancy factors of 0.504 (5) and 0.496 (5).
Keywords: crystal structure; peptide; hydrogen bonding; homopeptide.
CCDC reference: 1907978
1. Chemical context
In peptide stereochemistry, many studies have been performed in order to control the et al., 2014). Blout & Karlson (1958) reported that the of aspartic acid β-benzyl ester existed as a left-handed helix in solutions of halogenated hydrocarbones (CHCl3 and CCl2COOH), although early studies have clearly shown that a classical ordered α-helix structure in all-L is right handed because of the of their α-amino acid building blocks. Subsequently, this research topic was expanded by many other groups, and numerous β-esters have been investigated (Toniolo et al., 1968). In this work, we focus on the homo-tripeptide of Asp(OMe) as a simple model of the homo-polypeptide because of the difficulties in collecting X-ray diffraction data for polypeptides.
secondary structure. Among them, controlling helix handedness can greatly impact the design of some biological molecules such as molecular switches and the pharmaceutical lead like protein–protein interaction inhibitors (de Zotti2. Structural commentary
Table 1 shows selected torsion angles for the title tripeptide. The molecular structure of the tripeptide adopts an extended conformation of the backbone chain (Fig. 1) with the φ- and ψ-torsion angles being φ1 = −122.49 (17)°, φ2 = −116.98 (16)°, φ3 = −84.60 (18)°, ψ1 = 86.49 (17)° and ψ2 = 112.58 (16)°, residing in the β region of the Ramachandran plot. All three consecutive peptide residues are in an s-trans conformation with the ω-torsion angles being ω0A = 169.2 (3)°, ω0B = −167.9 (2)°, ω1 = −168.62 (12)° and ω2 = −173.95 (13)°. The side chains of Asp(OMe), N2—C21—C23—C24 and N3—C31—C33—C34, adopt a g+ conformation [χ2 = −66.56 (19)° and χ3 = −57.72 (17)°], which is the most preferred conformation of aspartic acid (Chakrabarti & Pal, 2001), while the terminal side chain of Asp(OMe), N1—C11—C13—C14, adopts a t conformation [χ1 = 172.69 (15)°].
|
3. Supramolecular features
In the crystal, all of the N atoms in the tripeptide are engaged in intermolecular N—H⋯O hydrogen bonds [N1—H1⋯O5Ai, N1—H1⋯O5Bi, N2—H2⋯O12ii and N3—H3⋯O22i; Table 2]. These hydrogen bonds and some C—H⋯O hydrogen bonds (C2A—H2A1⋯O4Aii, C13—H13⋯O5Ai, C13—H13⋯O5Bi, C31—H31⋯O35ii, C33—H33A⋯O41i and C41—H41A⋯O42ii; Table 2) link the molecules, forming an infinite parallel β-sheet structure along the b-axis direction (Fig. 2). Other C—H⋯O hydrogen bonds [C15—H15B⋯O34iii, C25—H25B⋯O32iv and C46–H46⋯O34v; Table 2] further link the β-sheets, forming a three-dimensional network (Fig. 3).
4. Database survey
A search of the Cambridge Structural Database (Version 5.39, updated November 2017; Groom et al., 2016) for homo-dipeptides and tripeptides of Asp and Asp β-esters yielded zero hits. A search for dipeptides having an Asp(OMe) residue yielded two hits [DOBWIA (Fuganti et al., 1986) and GABVEK (Mcharfi et al., 1986)]. DOBWIA, an α-L-aspartyl-L-phenylalanine derivative, has an extended intra- and intermolecular hydrogen-bonding network. GABVEK, an α-L-prolyl-L-aspartic acid derivative, shows a βI-turn conformation.
5. Synthesis and crystallization
The synthesis of the title homotripeptide, 6, was performed according to the scheme in Fig. 4.
Compound 1 was synthesized from L-aspartic acid according to a previously described method (Reddy et al., 2011; Ollivier et al., 2010). Yield: 61.2% 1H NMR (400 MHz, CDCl3): δ 1.45 (s, 9H, Boc t-butyl), 2.83–2.89 (m, 1H, Asp βH), 3.03–3.08 (m, 1H, Asp βH), 3.72 (s, 3H, Asp OCH3), 4.60–4.65 (m, 1H, Asp αH), 5.56 (d, J = 4.8 Hz, 1H, Asp NH).
Compound 2 was synthesized according to a slightly modified literature procedure (Wang et al., 1977). Compound 1 (7.05 g, 28.5 mmol) was dissolved in MeOH (20 mL) and 0.7 M aqueous Cs2CO3 solution (20 ml) was added. The mixture was evaporated to dryness and the residue was re-evaporated three times with EtOH. A mixture of the white solid cesium salt and phenacyl bromide (5.68 g, 28.5 mmol) in DMF (30 mL) was stirred for 15min, and the precipitated cesium bromide removed. The solution was evaporated to give the residue, which was diluted with ethyl acetate, washed with water, sat. aqueous NaHCO3, and dried over Na2SO4. The was filtered off and the filtrate evaporated under reduced pressure. Crystallization of the product from a mixture of ethyl acetate and hexane afforded colourless crystals. Yield 5.36 g (14.7 mmol, 51.5%). 1H NMR (400 MHz, CDCl3): δ 1.46 (s, 9H, Boc t-butyl), 2.93–2.99 (m, 1H, Asp βH), 3.07–3.12 (m, 1H, Asp βH), 3.74 (s, 3H, Asp OCH3), 4.77–4.82 (m, 1H, Asp αH), 5.35–5.48 (m, 2H, Pac CH2), 5.59 (d, J = 8.8 Hz, Asp NH), 7.47–7.52 (m, 2H, Pac phenyl), 7.60–7.64 (m, 1H, Pac phenyl), 7.89–7.91 (m, 2H, Pac phenyl).
Compound 3: Compound 2 (0.67 g, 2.72 mmol) was treated with 4.0 M HCl in dioxane for 60 min. The excess of HCl and solvent were evaporated and the residue was re-evaporated three times with MeOH, which was used for the next reaction without purification.
Compound 4: A solution of compound 1 (1.01 g, 2.72 mmol), compound 3 (2.72 mmol), 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluoridophosphate (HBTU; 1.24 g, 3.26 mmol), 1,2,3-benzotriazol-1-ol monohydrate (HOBt; 0.44 g, 3.26 mmol) and iPr2NEt (1.11 ml, 6.52 mmol) in DMF was stirred at room temperature for 20 h. The solution was then evaporated, diluted with ethyl acetate, washed with sat. aqueous KHSO4 and sat. aqueous NaHCO3, and dried over Na2SO4. After evaporation of the solvent, the residue was purified by on silica gel (50% EtOAc in n-hexane). Crystallization of the product from a mixture of ethyl acetate and hexane (v:v = 1:1) afforded colourless crystals. Yield 0.70 g (1.42 mmol, 52.4%). 1H NMR (400 MHz, CDCl3): δ 1.45 (s, 9H, Boc t-butyl), 2.71–3.03 (m, 2H, Asp βH), 2.95–3.13 (m, 2H, Asp βH), 3.70 (s, 3H, Asp OCH3), 3.75 (s, 3H, Asp OCH3), 4.58–4.60 (m, 1H, Asp αH), 5.03–5.08 (m, 1H, Asp αH), 5.35–5.47 (m, 2H, Pac CH2), 5.71 (d, J = 8.4 Hz, 1H, Asp NH), 7.47–7.51 (m, 2H, Pac phenyl), 7.58 (d, J = 8.4 Hz, 1H, Asp NH), 7.60–7.64 (m, 2H, Pac phenyl), 7.88–7.90 (m, 2H, Pac phenyl).
Compound 5: Compound 4 (101.2 mg, 0.212 mmol) was treated with 4.0 M HCl in dioxane for 60 min. The excess of HCl and solvent were evaporated and the residue was re-evaporated three times with MeOH, which was used for the next reaction without purification.
Compound 6: A solution of compound 1 (57.7 mg, 0.233 mmol), compound 5 (0.212 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSCHCl; 55.2 mg, 0.288 mmol), HOBt (37.1 mg, 0.275 mmol) and Et3N (71 µl, 0.509 mmol) in DMF was stirred at room temperature for 20 h. The solution was then evaporated, diluted with ethyl acetate, washed with sat. aqueous KHSO4 and sat. aqueous NaHCO3, and dried over Na2SO4. After evaporation of the solvent, the residue was purified by on silica gel (66% EtOAc in n–hexane). Crystallization of the product from a mixture of ethyl acetate and hexane (v:v = 1:1) afforded colourless crystals. Yield 77 mg (0.127 mmol, 59.9%). 1H NMR (400 MHz, CDCl3): δ 1.45 (s, 9H, Boc t-butyl), 2.72–2.82 (m, 2H, Asp βH), 2.96–3.04 (m, 4H, Asp βH), 3.69 (s, 3H, Asp OCH3), 3.71 (s, 3H, Asp OCH3), 3.74 (s, 3H, Asp OCH3), 4.52–4.56 (m,1H, Asp αH), 4.83–4.88 (m, 1H, Asp αH), 5.03–5.08 (m, 1H, Asp aH), 5.33–5.46 (m, 2H, Pac CH2), 5.65 (d, J = 8.4Hz, 1H, Asp NH), 7.47–7.51 (m, 1H, Pac phenyl), 7.60–7.64 (m, 3H, Pac phenyl, Asp NH), 7.87–7.89 (m, 2H, Pac phenyl). Single crystals suitable for X-ray diffraction were obtained by slow evaporation from a solution of acetone/water (19:1 v/v) mixture.
6. Refinement
Crystal data, data collection and structure . The Boc protecting group at the N-terminus of the peptide is disordered. The final occupancy ratio is 0.504 (5):0.496 (5). The C atoms of the disordered tert-butyl groups were refined with SIMU restraints and the C5—O5A and C5—O5B bonds were treated with DFIX restraints of 1.21 (1) Å. The N-bound H atoms were refined freely, while the other H atoms were placed in geometrically idealized positions (C—H = 0.95–1.00 Å) and refined as riding on their parent atoms, with Uiso(H) = 1.2Ueq(C) (or 1.5Ueq(C) for the methyl groups). The was known for the synthesized material.
details are summarized in Table 3
|
Supporting information
CCDC reference: 1907978
https://doi.org/10.1107/S2056989019004596/is5511sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019004596/is5511Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989019004596/is5511Isup3.cdx
Data collection: CrysAlis PRO (Rigaku OD, 2015); cell
CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).C28H37N3O13 | F(000) = 660 |
Mr = 623.60 | Dx = 1.367 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54184 Å |
a = 17.7734 (2) Å | Cell parameters from 5605 reflections |
b = 4.97864 (4) Å | θ = 4.8–74.0° |
c = 18.7681 (2) Å | µ = 0.93 mm−1 |
β = 114.2255 (14)° | T = 93 K |
V = 1514.49 (3) Å3 | Plate, colorless |
Z = 2 | 0.41 × 0.14 × 0.04 mm |
Rigaku Oxford Diffraction XtaLAB Pro: Kappa single diffractometer | 3952 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 3832 reflections with I > 2σ(I) |
Detector resolution: 5.811 pixels mm-1 | Rint = 0.018 |
ω scans | θmax = 74.4°, θmin = 2.6° |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2015) | h = −21→21 |
Tmin = 0.754, Tmax = 1.000 | k = −6→3 |
7024 measured reflections | l = −23→23 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.026 | w = 1/[σ2(Fo2) + (0.0741P)2 + 0.2745P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.072 | (Δ/σ)max < 0.001 |
S = 0.77 | Δρmax = 0.17 e Å−3 |
3952 reflections | Δρmin = −0.18 e Å−3 |
470 parameters | Absolute structure: Flack x determined using 629 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
21 restraints | Absolute structure parameter: 0.06 (12) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1A | 0.2144 (3) | 0.2721 (9) | 0.6848 (2) | 0.0345 (9) | 0.504 (5) |
H1A1 | 0.267469 | 0.355241 | 0.693593 | 0.052* | 0.504 (5) |
H1A2 | 0.220969 | 0.157562 | 0.729453 | 0.052* | 0.504 (5) |
H1A3 | 0.173686 | 0.412611 | 0.679050 | 0.052* | 0.504 (5) |
C2A | 0.2520 (6) | −0.0962 (18) | 0.6151 (5) | 0.0266 (13) | 0.504 (5) |
H2A1 | 0.231399 | −0.213264 | 0.569073 | 0.040* | 0.504 (5) |
H2A2 | 0.267358 | −0.205521 | 0.662432 | 0.040* | 0.504 (5) |
H2A3 | 0.300386 | 0.002635 | 0.616886 | 0.040* | 0.504 (5) |
C3A | 0.1022 (5) | −0.0283 (18) | 0.5951 (5) | 0.0263 (14) | 0.504 (5) |
H3A1 | 0.060178 | 0.111495 | 0.584750 | 0.039* | 0.504 (5) |
H3A2 | 0.106814 | −0.132737 | 0.640966 | 0.039* | 0.504 (5) |
H3A3 | 0.086230 | −0.147514 | 0.549665 | 0.039* | 0.504 (5) |
C4A | 0.1848 (4) | 0.102 (2) | 0.6103 (5) | 0.0217 (15) | 0.504 (5) |
O4A | 0.1746 (3) | 0.3070 (16) | 0.5505 (4) | 0.0261 (11) | 0.504 (5) |
O5A | 0.1213 (9) | 0.008 (2) | 0.4475 (13) | 0.024 (2) | 0.504 (5) |
C1B | 0.1534 (3) | 0.2751 (9) | 0.6701 (2) | 0.0328 (9) | 0.496 (5) |
H1B1 | 0.199436 | 0.402629 | 0.686695 | 0.049* | 0.496 (5) |
H1B2 | 0.159098 | 0.158167 | 0.714055 | 0.049* | 0.496 (5) |
H1B3 | 0.101223 | 0.373908 | 0.652870 | 0.049* | 0.496 (5) |
C2B | 0.2381 (6) | −0.0274 (18) | 0.6260 (6) | 0.0288 (14) | 0.496 (5) |
H2B1 | 0.237862 | −0.137167 | 0.582533 | 0.043* | 0.496 (5) |
H2B2 | 0.249930 | −0.141679 | 0.671843 | 0.043* | 0.496 (5) |
H2B3 | 0.280682 | 0.111625 | 0.638512 | 0.043* | 0.496 (5) |
C3B | 0.0818 (5) | −0.0926 (18) | 0.5758 (5) | 0.0254 (13) | 0.496 (5) |
H3B1 | 0.029814 | 0.006775 | 0.551414 | 0.038* | 0.496 (5) |
H3B2 | 0.082257 | −0.192873 | 0.620932 | 0.038* | 0.496 (5) |
H3B3 | 0.086929 | −0.218099 | 0.537838 | 0.038* | 0.496 (5) |
C4B | 0.1541 (5) | 0.105 (3) | 0.6028 (6) | 0.0212 (15) | 0.496 (5) |
O4B | 0.1433 (3) | 0.3082 (16) | 0.5416 (4) | 0.0220 (10) | 0.496 (5) |
O5B | 0.1396 (9) | 0.001 (2) | 0.4505 (12) | 0.024 (2) | 0.496 (5) |
C5 | 0.14313 (11) | 0.2319 (4) | 0.47256 (9) | 0.0202 (4) | |
N1 | 0.14230 (10) | 0.4450 (3) | 0.42909 (8) | 0.0207 (3) | |
H1 | 0.1496 (14) | 0.593 (6) | 0.4473 (13) | 0.025* | |
C11 | 0.12630 (9) | 0.4285 (4) | 0.34665 (8) | 0.0159 (3) | |
H11 | 0.119307 | 0.236491 | 0.329481 | 0.019* | |
C12 | 0.20103 (9) | 0.5508 (4) | 0.33717 (8) | 0.0152 (3) | |
O12 | 0.20389 (7) | 0.7897 (3) | 0.32340 (7) | 0.0207 (3) | |
C13 | 0.04814 (9) | 0.5864 (4) | 0.29904 (9) | 0.0198 (4) | |
H13A | 0.000362 | 0.496514 | 0.303103 | 0.024* | |
H13B | 0.052796 | 0.768642 | 0.321538 | 0.024* | |
C14 | 0.03251 (9) | 0.6103 (4) | 0.21412 (9) | 0.0191 (3) | |
O14 | 0.05911 (8) | 0.4612 (3) | 0.17994 (7) | 0.0285 (3) | |
C15 | −0.03784 (11) | 0.8735 (5) | 0.09979 (10) | 0.0293 (4) | |
H15A | −0.009289 | 1.036228 | 0.094924 | 0.044* | |
H15B | −0.097570 | 0.898998 | 0.072156 | 0.044* | |
H15C | −0.020654 | 0.721049 | 0.076939 | 0.044* | |
O15 | −0.01716 (7) | 0.8205 (3) | 0.18149 (7) | 0.0269 (3) | |
N2 | 0.26296 (8) | 0.3747 (3) | 0.34922 (8) | 0.0159 (3) | |
H2 | 0.2565 (12) | 0.199 (6) | 0.3536 (11) | 0.019* | |
C21 | 0.34413 (9) | 0.4635 (4) | 0.35689 (8) | 0.0156 (3) | |
H21 | 0.344606 | 0.663962 | 0.353802 | 0.019* | |
C22 | 0.36114 (9) | 0.3452 (4) | 0.28995 (9) | 0.0160 (3) | |
O22 | 0.37002 (7) | 0.1028 (3) | 0.28428 (6) | 0.0206 (3) | |
C23 | 0.41063 (9) | 0.3731 (4) | 0.43516 (8) | 0.0185 (4) | |
H23A | 0.406738 | 0.176533 | 0.440900 | 0.022* | |
H23B | 0.465823 | 0.413628 | 0.436741 | 0.022* | |
C24 | 0.40034 (9) | 0.5149 (4) | 0.50166 (9) | 0.0187 (3) | |
O24 | 0.36527 (8) | 0.7236 (3) | 0.49676 (7) | 0.0276 (3) | |
O25 | 0.43715 (7) | 0.3764 (3) | 0.56861 (6) | 0.0243 (3) | |
C25 | 0.43003 (11) | 0.4982 (5) | 0.63560 (9) | 0.0289 (4) | |
H25A | 0.450425 | 0.683342 | 0.641563 | 0.043* | |
H25B | 0.462802 | 0.395351 | 0.682707 | 0.043* | |
H25C | 0.372054 | 0.498328 | 0.627883 | 0.043* | |
N3 | 0.36442 (8) | 0.5253 (3) | 0.23773 (8) | 0.0165 (3) | |
H3 | 0.3610 (12) | 0.692 (5) | 0.2455 (12) | 0.020* | |
C31 | 0.37213 (9) | 0.4317 (4) | 0.16774 (8) | 0.0158 (3) | |
H31 | 0.340229 | 0.260920 | 0.150068 | 0.019* | |
C32 | 0.46177 (10) | 0.3789 (4) | 0.18265 (8) | 0.0173 (3) | |
O32 | 0.52056 (7) | 0.5030 (3) | 0.22640 (6) | 0.0235 (3) | |
C33 | 0.33705 (10) | 0.6411 (4) | 0.10194 (9) | 0.0179 (3) | |
H33A | 0.369066 | 0.810066 | 0.117588 | 0.021* | |
H33B | 0.340708 | 0.573229 | 0.053884 | 0.021* | |
C34 | 0.24805 (10) | 0.6920 (4) | 0.08698 (9) | 0.0183 (3) | |
O34 | 0.19207 (7) | 0.5396 (3) | 0.05273 (7) | 0.0262 (3) | |
O35 | 0.24040 (7) | 0.9215 (3) | 0.11951 (7) | 0.0227 (3) | |
C35 | 0.15959 (11) | 0.9750 (5) | 0.11807 (12) | 0.0319 (4) | |
H35A | 0.119401 | 0.996061 | 0.063845 | 0.048* | |
H35B | 0.161673 | 1.140387 | 0.147146 | 0.048* | |
H35C | 0.143100 | 0.824807 | 0.142250 | 0.048* | |
O41 | 0.46534 (7) | 0.1747 (3) | 0.13693 (7) | 0.0198 (3) | |
C41 | 0.54548 (10) | 0.1292 (4) | 0.13817 (10) | 0.0208 (4) | |
H41A | 0.546104 | −0.044984 | 0.112960 | 0.025* | |
H41B | 0.587062 | 0.121432 | 0.192914 | 0.025* | |
C42 | 0.56705 (10) | 0.3543 (4) | 0.09510 (9) | 0.0178 (3) | |
O42 | 0.51578 (7) | 0.5211 (3) | 0.05891 (6) | 0.0216 (3) | |
C43 | 0.65291 (10) | 0.3610 (4) | 0.09916 (8) | 0.0182 (3) | |
C44 | 0.67194 (10) | 0.5559 (4) | 0.05561 (9) | 0.0205 (4) | |
H44 | 0.630773 | 0.678584 | 0.024158 | 0.025* | |
C45 | 0.71356 (10) | 0.1801 (4) | 0.14514 (9) | 0.0217 (4) | |
H45 | 0.700557 | 0.045572 | 0.174190 | 0.026* | |
C46 | 0.75121 (11) | 0.5701 (4) | 0.05834 (9) | 0.0231 (4) | |
H46 | 0.764212 | 0.701551 | 0.028446 | 0.028* | |
C47 | 0.79299 (11) | 0.1973 (4) | 0.14827 (10) | 0.0246 (4) | |
H47 | 0.834544 | 0.076250 | 0.180023 | 0.030* | |
C48 | 0.81132 (10) | 0.3916 (5) | 0.10490 (10) | 0.0241 (4) | |
H48 | 0.865573 | 0.402778 | 0.107059 | 0.029* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1A | 0.068 (2) | 0.0176 (18) | 0.0219 (14) | 0.000 (2) | 0.0225 (18) | 0.0003 (14) |
C2A | 0.029 (3) | 0.026 (4) | 0.026 (2) | 0.003 (3) | 0.0132 (15) | 0.003 (2) |
C3A | 0.029 (4) | 0.026 (4) | 0.030 (4) | 0.001 (3) | 0.018 (3) | 0.008 (2) |
C4A | 0.038 (4) | 0.015 (2) | 0.016 (2) | −0.001 (5) | 0.015 (4) | 0.003 (2) |
O4A | 0.049 (3) | 0.0146 (17) | 0.0160 (18) | −0.003 (3) | 0.014 (3) | −0.0002 (14) |
O5A | 0.036 (5) | 0.016 (3) | 0.025 (3) | −0.003 (2) | 0.018 (4) | −0.003 (2) |
C1B | 0.067 (2) | 0.0182 (18) | 0.0208 (14) | −0.005 (2) | 0.0254 (17) | 0.0008 (14) |
C2B | 0.029 (3) | 0.027 (4) | 0.029 (3) | 0.001 (3) | 0.0113 (17) | 0.007 (3) |
C3B | 0.028 (3) | 0.021 (4) | 0.030 (4) | −0.005 (2) | 0.015 (3) | 0.006 (2) |
C4B | 0.033 (4) | 0.015 (2) | 0.018 (2) | 0.001 (4) | 0.012 (3) | 0.0045 (19) |
O4B | 0.040 (3) | 0.0113 (16) | 0.0166 (18) | −0.005 (3) | 0.013 (2) | −0.0007 (14) |
O5B | 0.044 (6) | 0.011 (2) | 0.021 (2) | 0.005 (2) | 0.016 (4) | 0.0022 (17) |
C5 | 0.0293 (8) | 0.0167 (9) | 0.0176 (7) | 0.0000 (8) | 0.0127 (6) | −0.0003 (7) |
N1 | 0.0357 (8) | 0.0124 (8) | 0.0170 (6) | −0.0036 (7) | 0.0137 (6) | −0.0031 (6) |
C11 | 0.0205 (7) | 0.0154 (9) | 0.0142 (6) | −0.0015 (7) | 0.0094 (6) | −0.0012 (6) |
C12 | 0.0184 (7) | 0.0139 (9) | 0.0131 (6) | 0.0002 (7) | 0.0063 (5) | 0.0002 (6) |
O12 | 0.0210 (6) | 0.0148 (7) | 0.0272 (6) | 0.0008 (5) | 0.0109 (5) | 0.0030 (5) |
C13 | 0.0197 (7) | 0.0219 (9) | 0.0205 (7) | 0.0003 (7) | 0.0110 (6) | −0.0001 (7) |
C14 | 0.0153 (7) | 0.0205 (9) | 0.0196 (7) | −0.0035 (7) | 0.0054 (6) | −0.0002 (7) |
O14 | 0.0373 (7) | 0.0275 (8) | 0.0216 (5) | 0.0052 (6) | 0.0129 (5) | −0.0007 (6) |
C15 | 0.0243 (8) | 0.0346 (12) | 0.0245 (8) | 0.0022 (9) | 0.0055 (6) | 0.0090 (9) |
O15 | 0.0246 (6) | 0.0292 (8) | 0.0251 (6) | 0.0084 (6) | 0.0083 (5) | 0.0071 (6) |
N2 | 0.0177 (6) | 0.0113 (8) | 0.0195 (6) | −0.0010 (6) | 0.0083 (5) | 0.0005 (6) |
C21 | 0.0166 (7) | 0.0149 (9) | 0.0166 (7) | −0.0003 (6) | 0.0083 (5) | −0.0003 (7) |
C22 | 0.0142 (7) | 0.0167 (10) | 0.0167 (7) | −0.0006 (7) | 0.0061 (6) | 0.0001 (7) |
O22 | 0.0303 (6) | 0.0141 (7) | 0.0193 (5) | 0.0017 (5) | 0.0119 (5) | 0.0000 (5) |
C23 | 0.0195 (7) | 0.0188 (9) | 0.0169 (7) | 0.0024 (7) | 0.0072 (6) | 0.0002 (7) |
C24 | 0.0181 (7) | 0.0216 (9) | 0.0152 (7) | −0.0017 (8) | 0.0055 (5) | 0.0003 (7) |
O24 | 0.0384 (7) | 0.0232 (8) | 0.0205 (5) | 0.0077 (6) | 0.0114 (5) | −0.0015 (6) |
O25 | 0.0315 (6) | 0.0260 (7) | 0.0149 (5) | 0.0023 (6) | 0.0091 (4) | 0.0008 (5) |
C25 | 0.0366 (9) | 0.0360 (12) | 0.0160 (7) | −0.0002 (10) | 0.0127 (7) | −0.0015 (8) |
N3 | 0.0232 (6) | 0.0125 (8) | 0.0173 (6) | −0.0011 (6) | 0.0119 (5) | −0.0024 (6) |
C31 | 0.0198 (7) | 0.0136 (9) | 0.0160 (6) | −0.0015 (6) | 0.0095 (5) | −0.0019 (6) |
C32 | 0.0233 (7) | 0.0152 (9) | 0.0159 (6) | 0.0000 (7) | 0.0106 (6) | 0.0019 (7) |
O32 | 0.0214 (5) | 0.0270 (7) | 0.0217 (5) | −0.0035 (6) | 0.0085 (4) | −0.0061 (6) |
C33 | 0.0210 (7) | 0.0172 (9) | 0.0172 (7) | −0.0015 (7) | 0.0096 (6) | 0.0004 (7) |
C34 | 0.0227 (8) | 0.0181 (9) | 0.0143 (6) | −0.0004 (7) | 0.0078 (6) | 0.0029 (7) |
O34 | 0.0236 (6) | 0.0286 (8) | 0.0235 (5) | −0.0072 (6) | 0.0066 (5) | −0.0050 (6) |
O35 | 0.0214 (6) | 0.0189 (7) | 0.0319 (6) | −0.0008 (5) | 0.0151 (5) | −0.0021 (6) |
C35 | 0.0280 (9) | 0.0298 (12) | 0.0474 (10) | 0.0047 (9) | 0.0249 (8) | 0.0057 (10) |
O41 | 0.0218 (5) | 0.0169 (7) | 0.0252 (5) | −0.0009 (5) | 0.0142 (4) | −0.0043 (5) |
C41 | 0.0224 (8) | 0.0177 (10) | 0.0279 (8) | 0.0014 (7) | 0.0159 (7) | 0.0001 (7) |
C42 | 0.0242 (7) | 0.0147 (9) | 0.0162 (6) | −0.0011 (7) | 0.0102 (6) | −0.0049 (7) |
O42 | 0.0246 (6) | 0.0195 (7) | 0.0221 (5) | 0.0029 (5) | 0.0107 (4) | 0.0010 (5) |
C43 | 0.0236 (8) | 0.0164 (9) | 0.0163 (6) | −0.0018 (7) | 0.0098 (6) | −0.0030 (7) |
C44 | 0.0251 (8) | 0.0188 (10) | 0.0181 (7) | −0.0009 (7) | 0.0094 (6) | −0.0017 (7) |
C45 | 0.0268 (8) | 0.0195 (10) | 0.0215 (7) | 0.0007 (8) | 0.0126 (6) | 0.0009 (7) |
C46 | 0.0298 (8) | 0.0219 (10) | 0.0216 (7) | −0.0063 (8) | 0.0145 (7) | −0.0031 (7) |
C47 | 0.0236 (8) | 0.0240 (10) | 0.0255 (8) | 0.0014 (8) | 0.0093 (6) | −0.0014 (8) |
C48 | 0.0225 (8) | 0.0275 (10) | 0.0249 (8) | −0.0052 (8) | 0.0123 (6) | −0.0063 (8) |
C1A—C4A | 1.532 (11) | N2—H2 | 0.89 (3) |
C1A—H1A1 | 0.9800 | C21—C22 | 1.526 (2) |
C1A—H1A2 | 0.9800 | C21—C23 | 1.527 (2) |
C1A—H1A3 | 0.9800 | C21—H21 | 1.0000 |
C2A—C4A | 1.521 (10) | C22—O22 | 1.227 (2) |
C2A—H2A1 | 0.9800 | C22—N3 | 1.347 (2) |
C2A—H2A2 | 0.9800 | C23—C24 | 1.509 (2) |
C2A—H2A3 | 0.9800 | C23—H23A | 0.9900 |
C3A—C4A | 1.521 (10) | C23—H23B | 0.9900 |
C3A—H3A1 | 0.9800 | C24—O24 | 1.196 (2) |
C3A—H3A2 | 0.9800 | C24—O25 | 1.345 (2) |
C3A—H3A3 | 0.9800 | O25—C25 | 1.447 (2) |
C4A—O4A | 1.473 (13) | C25—H25A | 0.9800 |
O4A—C5 | 1.387 (7) | C25—H25B | 0.9800 |
O5A—C5 | 1.212 (9) | C25—H25C | 0.9800 |
C1B—C4B | 1.527 (11) | N3—C31 | 1.4522 (19) |
C1B—H1B1 | 0.9800 | N3—H3 | 0.85 (3) |
C1B—H1B2 | 0.9800 | C31—C32 | 1.523 (2) |
C1B—H1B3 | 0.9800 | C31—C33 | 1.539 (2) |
C2B—C4B | 1.523 (10) | C31—H31 | 1.0000 |
C2B—H2B1 | 0.9800 | C32—O32 | 1.202 (2) |
C2B—H2B2 | 0.9800 | C32—O41 | 1.348 (2) |
C2B—H2B3 | 0.9800 | C33—C34 | 1.510 (2) |
C3B—C4B | 1.529 (10) | C33—H33A | 0.9900 |
C3B—H3B1 | 0.9800 | C33—H33B | 0.9900 |
C3B—H3B2 | 0.9800 | C34—O34 | 1.206 (2) |
C3B—H3B3 | 0.9800 | C34—O35 | 1.328 (2) |
C4B—O4B | 1.484 (13) | O35—C35 | 1.450 (2) |
O4B—C5 | 1.348 (7) | C35—H35A | 0.9800 |
O5B—C5 | 1.216 (9) | C35—H35B | 0.9800 |
C5—N1 | 1.335 (2) | C35—H35C | 0.9800 |
N1—C11 | 1.4563 (18) | O41—C41 | 1.4329 (19) |
N1—H1 | 0.80 (3) | C41—C42 | 1.520 (2) |
C11—C13 | 1.526 (2) | C41—H41A | 0.9900 |
C11—C12 | 1.536 (2) | C41—H41B | 0.9900 |
C11—H11 | 1.0000 | C42—O42 | 1.214 (2) |
C12—O12 | 1.222 (2) | C42—C43 | 1.497 (2) |
C12—N2 | 1.352 (2) | C43—C44 | 1.397 (2) |
C13—C14 | 1.506 (2) | C43—C45 | 1.398 (2) |
C13—H13A | 0.9900 | C44—C46 | 1.390 (2) |
C13—H13B | 0.9900 | C44—H44 | 0.9500 |
C14—O14 | 1.198 (2) | C45—C47 | 1.391 (2) |
C14—O15 | 1.344 (2) | C45—H45 | 0.9500 |
C15—O15 | 1.447 (2) | C46—C48 | 1.389 (3) |
C15—H15A | 0.9800 | C46—H46 | 0.9500 |
C15—H15B | 0.9800 | C47—C48 | 1.386 (3) |
C15—H15C | 0.9800 | C47—H47 | 0.9500 |
N2—C21 | 1.4586 (19) | C48—H48 | 0.9500 |
C4A—C1A—H1A1 | 109.5 | C12—N2—C21 | 121.62 (16) |
C4A—C1A—H1A2 | 109.5 | C12—N2—H2 | 121.7 (14) |
H1A1—C1A—H1A2 | 109.5 | C21—N2—H2 | 116.7 (13) |
C4A—C1A—H1A3 | 109.5 | N2—C21—C22 | 108.90 (13) |
H1A1—C1A—H1A3 | 109.5 | N2—C21—C23 | 110.44 (13) |
H1A2—C1A—H1A3 | 109.5 | C22—C21—C23 | 109.98 (13) |
C4A—C2A—H2A1 | 109.5 | N2—C21—H21 | 109.2 |
C4A—C2A—H2A2 | 109.5 | C22—C21—H21 | 109.2 |
H2A1—C2A—H2A2 | 109.5 | C23—C21—H21 | 109.2 |
C4A—C2A—H2A3 | 109.5 | O22—C22—N3 | 123.09 (15) |
H2A1—C2A—H2A3 | 109.5 | O22—C22—C21 | 121.80 (15) |
H2A2—C2A—H2A3 | 109.5 | N3—C22—C21 | 115.11 (16) |
C4A—C3A—H3A1 | 109.5 | C24—C23—C21 | 110.43 (14) |
C4A—C3A—H3A2 | 109.5 | C24—C23—H23A | 109.6 |
H3A1—C3A—H3A2 | 109.5 | C21—C23—H23A | 109.6 |
C4A—C3A—H3A3 | 109.5 | C24—C23—H23B | 109.6 |
H3A1—C3A—H3A3 | 109.5 | C21—C23—H23B | 109.6 |
H3A2—C3A—H3A3 | 109.5 | H23A—C23—H23B | 108.1 |
O4A—C4A—C2A | 110.1 (7) | O24—C24—O25 | 123.78 (15) |
O4A—C4A—C3A | 110.1 (6) | O24—C24—C23 | 125.39 (15) |
C2A—C4A—C3A | 114.2 (9) | O25—C24—C23 | 110.82 (16) |
O4A—C4A—C1A | 101.5 (8) | C24—O25—C25 | 114.48 (15) |
C2A—C4A—C1A | 109.8 (6) | O25—C25—H25A | 109.5 |
C3A—C4A—C1A | 110.5 (7) | O25—C25—H25B | 109.5 |
C5—O4A—C4A | 119.1 (7) | H25A—C25—H25B | 109.5 |
C4B—C1B—H1B1 | 109.5 | O25—C25—H25C | 109.5 |
C4B—C1B—H1B2 | 109.5 | H25A—C25—H25C | 109.5 |
H1B1—C1B—H1B2 | 109.5 | H25B—C25—H25C | 109.5 |
C4B—C1B—H1B3 | 109.5 | C22—N3—C31 | 119.51 (15) |
H1B1—C1B—H1B3 | 109.5 | C22—N3—H3 | 119.8 (14) |
H1B2—C1B—H1B3 | 109.5 | C31—N3—H3 | 120.7 (14) |
C4B—C2B—H2B1 | 109.5 | N3—C31—C32 | 111.65 (12) |
C4B—C2B—H2B2 | 109.5 | N3—C31—C33 | 110.54 (14) |
H2B1—C2B—H2B2 | 109.5 | C32—C31—C33 | 108.24 (12) |
C4B—C2B—H2B3 | 109.5 | N3—C31—H31 | 108.8 |
H2B1—C2B—H2B3 | 109.5 | C32—C31—H31 | 108.8 |
H2B2—C2B—H2B3 | 109.5 | C33—C31—H31 | 108.8 |
C4B—C3B—H3B1 | 109.5 | O32—C32—O41 | 124.59 (15) |
C4B—C3B—H3B2 | 109.5 | O32—C32—C31 | 125.98 (16) |
H3B1—C3B—H3B2 | 109.5 | O41—C32—C31 | 109.40 (13) |
C4B—C3B—H3B3 | 109.5 | C34—C33—C31 | 108.13 (12) |
H3B1—C3B—H3B3 | 109.5 | C34—C33—H33A | 110.1 |
H3B2—C3B—H3B3 | 109.5 | C31—C33—H33A | 110.1 |
O4B—C4B—C2B | 108.5 (6) | C34—C33—H33B | 110.1 |
O4B—C4B—C3B | 111.0 (7) | C31—C33—H33B | 110.1 |
C2B—C4B—C3B | 114.2 (10) | H33A—C33—H33B | 108.4 |
O4B—C4B—C1B | 102.7 (8) | O34—C34—O35 | 124.64 (15) |
C2B—C4B—C1B | 110.1 (7) | O34—C34—C33 | 124.45 (17) |
C3B—C4B—C1B | 109.8 (6) | O35—C34—C33 | 110.85 (14) |
C5—O4B—C4B | 120.0 (7) | C34—O35—C35 | 115.91 (15) |
O5A—C5—N1 | 125.0 (11) | O35—C35—H35A | 109.5 |
O5B—C5—N1 | 124.0 (11) | O35—C35—H35B | 109.5 |
O5B—C5—O4B | 124.9 (11) | H35A—C35—H35B | 109.5 |
N1—C5—O4B | 111.0 (4) | O35—C35—H35C | 109.5 |
O5A—C5—O4A | 125.8 (12) | H35A—C35—H35C | 109.5 |
N1—C5—O4A | 109.2 (4) | H35B—C35—H35C | 109.5 |
C5—N1—C11 | 123.55 (15) | C32—O41—C41 | 114.52 (13) |
C5—N1—H1 | 120.9 (16) | O41—C41—C42 | 109.92 (14) |
C11—N1—H1 | 115.6 (16) | O41—C41—H41A | 109.7 |
N1—C11—C13 | 109.09 (13) | C42—C41—H41A | 109.7 |
N1—C11—C12 | 107.42 (12) | O41—C41—H41B | 109.7 |
C13—C11—C12 | 110.52 (13) | C42—C41—H41B | 109.7 |
N1—C11—H11 | 109.9 | H41A—C41—H41B | 108.2 |
C13—C11—H11 | 109.9 | O42—C42—C43 | 121.93 (16) |
C12—C11—H11 | 109.9 | O42—C42—C41 | 120.44 (15) |
O12—C12—N2 | 124.40 (16) | C43—C42—C41 | 117.63 (15) |
O12—C12—C11 | 121.54 (15) | C44—C43—C45 | 119.89 (15) |
N2—C12—C11 | 113.98 (15) | C44—C43—C42 | 118.18 (15) |
C14—C13—C11 | 112.88 (13) | C45—C43—C42 | 121.93 (16) |
C14—C13—H13A | 109.0 | C46—C44—C43 | 119.93 (16) |
C11—C13—H13A | 109.0 | C46—C44—H44 | 120.0 |
C14—C13—H13B | 109.0 | C43—C44—H44 | 120.0 |
C11—C13—H13B | 109.0 | C47—C45—C43 | 119.89 (17) |
H13A—C13—H13B | 107.8 | C47—C45—H45 | 120.1 |
O14—C14—O15 | 124.62 (15) | C43—C45—H45 | 120.1 |
O14—C14—C13 | 125.16 (17) | C48—C46—C44 | 119.78 (17) |
O15—C14—C13 | 110.21 (15) | C48—C46—H46 | 120.1 |
O15—C15—H15A | 109.5 | C44—C46—H46 | 120.1 |
O15—C15—H15B | 109.5 | C48—C47—C45 | 119.80 (17) |
H15A—C15—H15B | 109.5 | C48—C47—H47 | 120.1 |
O15—C15—H15C | 109.5 | C45—C47—H47 | 120.1 |
H15A—C15—H15C | 109.5 | C47—C48—C46 | 120.71 (16) |
H15B—C15—H15C | 109.5 | C47—C48—H48 | 119.6 |
C14—O15—C15 | 117.30 (14) | C46—C48—H48 | 119.6 |
C2A—C4A—O4A—C5 | 67.6 (7) | C21—C23—C24—O24 | −22.5 (2) |
C3A—C4A—O4A—C5 | −59.1 (8) | C21—C23—C24—O25 | 158.28 (14) |
C1A—C4A—O4A—C5 | −176.2 (4) | O24—C24—O25—C25 | 1.0 (2) |
C2B—C4B—O4B—C5 | 61.7 (8) | C23—C24—O25—C25 | −179.82 (14) |
C3B—C4B—O4B—C5 | −64.5 (8) | O22—C22—N3—C31 | 5.2 (2) |
C1B—C4B—O4B—C5 | 178.2 (4) | C21—C22—N3—C31 | −173.95 (13) |
C4B—O4B—C5—O5B | 11.0 (10) | C22—N3—C31—C32 | −84.60 (18) |
C4B—O4B—C5—N1 | −172.8 (4) | C22—N3—C31—C33 | 154.84 (14) |
C4A—O4A—C5—O5A | 1.2 (10) | N3—C31—C32—O32 | −34.3 (2) |
C4A—O4A—C5—N1 | −177.4 (4) | C33—C31—C32—O32 | 87.64 (19) |
O5A—C5—N1—C11 | −9.4 (9) | N3—C31—C32—O41 | 147.76 (14) |
O5B—C5—N1—C11 | 8.3 (9) | C33—C31—C32—O41 | −90.35 (16) |
O4B—C5—N1—C11 | −167.9 (2) | N3—C31—C33—C34 | −57.72 (17) |
O4A—C5—N1—C11 | 169.2 (3) | C32—C31—C33—C34 | 179.70 (14) |
C5—N1—C11—C13 | 117.68 (19) | C31—C33—C34—O34 | −75.17 (19) |
C5—N1—C11—C12 | −122.49 (17) | C31—C33—C34—O35 | 102.17 (16) |
N1—C11—C12—O12 | −90.42 (18) | O34—C34—O35—C35 | 5.2 (2) |
C13—C11—C12—O12 | 28.5 (2) | C33—C34—O35—C35 | −172.12 (14) |
N1—C11—C12—N2 | 86.49 (17) | O32—C32—O41—C41 | −5.8 (2) |
C13—C11—C12—N2 | −154.60 (13) | C31—C32—O41—C41 | 172.21 (13) |
N1—C11—C13—C14 | 172.69 (15) | C32—O41—C41—C42 | −71.55 (17) |
C12—C11—C13—C14 | 54.80 (19) | O41—C41—C42—O42 | −7.9 (2) |
C11—C13—C14—O14 | 22.9 (3) | O41—C41—C42—C43 | 172.15 (13) |
C11—C13—C14—O15 | −158.40 (14) | O42—C42—C43—C44 | −4.2 (2) |
O14—C14—O15—C15 | −1.8 (3) | C41—C42—C43—C44 | 175.78 (15) |
C13—C14—O15—C15 | 179.47 (15) | O42—C42—C43—C45 | 175.55 (16) |
O12—C12—N2—C21 | 8.2 (2) | C41—C42—C43—C45 | −4.5 (2) |
C11—C12—N2—C21 | −168.62 (12) | C45—C43—C44—C46 | −0.3 (3) |
C12—N2—C21—C22 | −116.98 (16) | C42—C43—C44—C46 | 179.46 (15) |
C12—N2—C21—C23 | 122.15 (16) | C44—C43—C45—C47 | 1.0 (3) |
N2—C21—C22—O22 | −66.5 (2) | C42—C43—C45—C47 | −178.75 (16) |
C23—C21—C22—O22 | 54.6 (2) | C43—C44—C46—C48 | −0.5 (3) |
N2—C21—C22—N3 | 112.58 (16) | C43—C45—C47—C48 | −0.9 (3) |
C23—C21—C22—N3 | −126.27 (15) | C45—C47—C48—C46 | 0.1 (3) |
N2—C21—C23—C24 | −66.56 (19) | C44—C46—C48—C47 | 0.6 (3) |
C22—C21—C23—C24 | 173.22 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O5Ai | 0.80 (3) | 2.13 (3) | 2.867 (11) | 154 (2) |
N1—H1···O5Bi | 0.80 (3) | 2.04 (3) | 2.800 (10) | 158 (2) |
N2—H2···O12ii | 0.89 (3) | 2.22 (3) | 3.066 (2) | 159.5 (18) |
N3—H3···O22i | 0.85 (2) | 2.16 (2) | 2.995 (2) | 170.1 (19) |
C2A—H2A1···O4Aii | 0.98 | 2.56 | 3.290 (12) | 131 |
C13—H13B···O5Ai | 0.99 | 2.48 | 3.300 (18) | 140 |
C13—H13B···O5Bi | 0.99 | 2.55 | 3.345 (17) | 137 |
C15—H15B···O34iii | 0.98 | 2.36 | 3.155 (2) | 138 |
C25—H25B···O32iv | 0.98 | 2.53 | 3.419 (2) | 151 |
C31—H31···O35ii | 1.00 | 2.34 | 3.319 (2) | 164 |
C33—H33A···O41i | 0.99 | 2.42 | 3.385 (2) | 165 |
C41—H41A···O42ii | 0.99 | 2.35 | 3.319 (2) | 165 |
C46—H46···O34v | 0.95 | 2.59 | 3.543 (3) | 176 |
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z; (iii) −x, y+1/2, −z; (iv) −x+1, y−1/2, −z+1; (v) −x+1, y+1/2, −z. |
Name | Atoms | Torsion angle |
ω0A | O4A—C5—N1—C11 | 169.2 (3) |
ω0B | O4B—C5—N1—C11 | -167.9 (2) |
φ1 | C5—N1—C11—C12 | -122.49 (17) |
ψ1 | N1—C11—C12—N2 | 86.49 (17) |
ω1 | C11—C12—N2—C21 | -168.62 (12) |
φ2 | C12—N2—C21—C22 | -116.98 (16) |
ψ2 | N2—C21—C22—N3 | 112.58 (16) |
ω2 | C21—C22—N3—C31 | -173.95 (13) |
φ3 | C22—N3—C31—C32 | -84.60 (18) |
χ1 | N1—C11—C13—C14 | 172.69 (15) |
χ2 | N2—C21—C23—C24 | -66.56 (19) |
χ3 | N3—C31—C33—C34 | -57.72 (17) |
Acknowledgements
This work was performed in part under the Cooperative Research Program of the Institute for Protein Research, Osaka University (CR-18–05).
Funding information
Funding for this research was provided by: Grant-in-Aid for Research Activity Start-up (grant No. JP17H07269).
References
Blout, E. R. & Karlson, R. H. (1958). J. Am. Chem. Soc. 80, 1259–1260. CrossRef CAS Web of Science Google Scholar
Chakrabarti, P. & Pal, D. (2001). Prog. Biophys. Mol. Biol. 76, 1–102. Web of Science CrossRef PubMed CAS Google Scholar
De Zotti, M., Formaggio, F., Crisma, M., Peggion, C., Moretto, A. & Toniolo, C. (2014). J. Pept. Sci. 20, 307–322. CAS PubMed Google Scholar
Fuganti, C., Grasselli, P., Malpezzi, L. & Casati, P. (1986). J. Org. Chem. 51, 1126–1128. CSD CrossRef CAS Web of Science Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Mcharfi, M., Aubry, A., Boussard, G. & Marraud, M. (1986). Eur. Biophys. J. 14, 43–51. CSD CrossRef CAS Google Scholar
Ollivier, A., Sinibaldi, M. E., Toupet, L., Traïkia, M. & Canet, I. (2010). Tetrahedron Lett. 51, 4147–4149. Web of Science CSD CrossRef CAS Google Scholar
Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259. Web of Science CrossRef CAS IUCr Journals Google Scholar
Reddy, C. R. & Latha, B. (2011). Tetrahedron Asymmetry, 22, 1849–1854. Web of Science CrossRef CAS Google Scholar
Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Toniolo, C., Falxa, M. L. & Goodman, M. (1968). Biopolymers, 6, 1579–1603. CrossRef CAS PubMed Web of Science Google Scholar
Wang, S. S., Gisin, B. F., Winter, D. P., Makofske, R., Kulesha, I. D., Tzougraki, C. & Meienhofer, J. (1977). J. Org. Chem. 42, 1286–1290. CrossRef CAS PubMed Web of Science Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.