research communications
Crystal structures of three newly synthesized flavanone hydrazones
aDepartment of Biochemistry and Molecular Biology Pennsylvania State University, University Park, PA 16802, USA, and bPennsylvania State University, Brandywine Campus, 25 Yearsley Mill Road, Media, Pa 19063, USA
*Correspondence e-mail: ajs8621@psu.edu
The crystal structures of racemic mixtures of three new flavanone-hydrazones in the centrosymmetric P), are reported. The structures of (±,E)-N′-[5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-ylidene]-2-(naphthalen-1-yl)acetohydrazide ethyl acetate monosolvate, C27H22N2O5·C4H8O2, and of (±,E)-N′-[5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-ylidene]-4-hydroxybenzohydrazide ethanol monosolvate, C22H18N2O6·C2H5OH, both exhibit an intramolecular O—H⋯N and multiple intermolecular O—H⋯O and C—H⋯O-type hydrogen bonds. The third structure, that of (±,E)-N′-(6-methoxy-2-phenylchroman-4-ylidene)-2-(naphthalen-1-yloxy)acetohydrazide, C28H24N2O4, has only one intermolecular N—H⋯O-type hydrogen bond. In each of the three cases, the crystal packings are stabilized by π–π stacking interactions between various aromatic components of symmetry-related molecules. The chiral carbon atom of the substituted chromane ring system in each case is puckered away from rest of the ring system.
(Keywords: crystal structure; naringenin; hydrazone; flavanone; flavonoid.
1. Chemical context
et al., 2016). As a result of their biologically privileged scaffold, and their synthetic derivatives are of significant interest to the medicinal chemistry community as potential treatments of disease. We recently reported the first of a hydrazone derivative of naringenin, (R/S,E)-2-(4-hydroxyphenyl)-4-(2-phenylhydrazineylidene)chromane-5,7-diol, a biologically active compound that has been reported to induce apoptosis in human cervical cancer cells (Yennawar & Sigmon, 2022; Kim et al., 2012). To further explore the medicinal potential of this class of compounds, three new flavonoid hydrazone compounds have been synthesized and structurally characterized. The three novel compounds are: (±,E)-N′-[5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-ylidene]-2-(naphthalen-1-yl)acetohydrazide ethyl acetate monosolvate (I), (±,E)-N′-(5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-ylidene)-4-hydroxybenzohydrazide ethanol monosolvate (II) and, (±,E)-N′-(6-methoxy-2-phenylchroman-4-ylidene)-2-(naphthalen-1-yloxy)-acetohydrazide (III).
encompass a family of organic, naturally occurring polyphenolic compounds with a general structure consisting of a 15-carbon skeleton containing two phenyl rings and a heterocyclic ring. include various subcategories – flavones, flavanones, flavanols, isoflavones, – all of which have demonstrated differential health benefits such as anti-oxidative, anti-inflammatory, anti-mutagenic, and anti-carcinogenic properties (Panche2. Structural commentary
Each of the three title compounds (Figs. 1, 2 and 3) has a carbon–nitrogen double bond [N1=C1: 1.291 (3), 1.294 (4) and 1.284 (5) Å] and all are in the E isomeric form. The pyran ring of the chromane ring system in each structure has an envelope pucker with values of the puckering amplitude Q of 0.423 (3), 0.397 (6), 0.331 (5) Å, and of θ = 57.9 (4), 53.9 (6), 58.1 (7)°, respectively. The chiral carbon (C8) in each case is displaced between 0.454 and 0.580 Å from the chromane ring planes. The puckering is similar to that seen in the previously reported structure (Yennawar & Sigmon, 2022).
In compound I, the disordered fractions (65/35%) of the 4-hydroxyphenyl ring makes dihedral angles of 77.128 (5) and 83.872 (5)°, respectively, with the chromane ring system. An intramolecular O—H⋯N hydrogen bond exists between one of the hydroxy groups on the chromane ring and the nitrogen of the hydrazone group [O—H⋯N = 2.527 (2) Å, 147°]. Another hydroxy group on the chromane ring participates in a hydrogen bond with the carbonyl group of the solvent ethyl acetate molecule [O2—H2⋯O6 = 2.720 (3) Å, 173°]. The naphthalene ring system is close to perpendicular to the chromane ring system [dihedral angle 77.692 (5)°].
In II, the 4-hydroxyphenyl ring of the hydrazone moiety is coplanar with the chromane ring [dihedral angle of 2.485 (3)° with the chromane ring system] whereas the other hydroxyphenyl ring is almost perpendicular [75.449 (5)°] to the chromane ring system. The chiral carbon of chromane ring (C8_1) and the methyl carbon (C2_1) of the solvent molecule show positional disorder. An intramolecular O—H⋯N hydrogen bond exists between one of the hydroxy groups on the chromane ring and the nitrogen of the hydrazone group [O3—H3⋯N1 = 2.542 (3) Å, 147°].
In III, the phenyl ring makes a dihedral angle of 86.17 (1)° with the chromane ring system, while the naphthalene ring system is perpendicular to the chromane ring system [dihedral angle = 89.65 (1)°].
3. Supramolecular features
The extended packing of both I and II (Figs. 4 and 5) exhibit intermolecular O—H⋯O and C—H⋯O-type interactions. Additionally II has N—H⋯O-type interactions (Tables 1 and 2). Both these packings have solvent molecules, namely ethyl acetate and ethanol, respectively, which interact with the parent molecules via O—H⋯O-type hydrogen bonds. In I, π–π interactions between the chromane rings of symmetry-related neighbors in the [101] direction are observed. The hydroxyphenyl rings also show similar stacking with their symmetry-related counterparts along the [10] direction. Partial stacking (π–π) interactions [centroid–centroid distance = 4.51 (1) Å] are observed between the chromane unit and the 4-hydroxyphenyl ring of the hydrazone moiety.
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In III (Fig. 6) the hydrogen-bond interaction is limited to one N—H⋯O-type hydrogen bond between the hydrazone group and carbonyl oxygen of a symmetry-related neighbor [N2—H2⋯O3 = 2.922 (4) Å, 167°], in a parallel, mutual give-and-take fashion (Table 3). Parallel, partial stacking between symmetry-related naphthalene rings [centroid–centroid distance = 3.790 (2) Å], and also between the chromane ring system and the hydrazone group of neighboring molecules [centroid–centroid distance = 3.730 (3) Å] further stabilizes the packing.
4. Database survey
A structure search was performed in Scifinder and Reaxys, and no identical structures were found. A text search (`flavanone' and `chroman-4-ylidene' and `chromane-5,7-diol' and `benzopyran-4-ylidene' and `chromen-4-ylidene') was performed in the CCDC's free Access Structures online database (Groom et al., 2016; accessed January, 2023). Six structures were found of hydrazone derivatives of flavanones, including our previously reported naringenin derivative (Yennawar & Sigmon, 2022). No crystal structures were found of flavanone containing a naphthalene moiety. Examples of other flavanone for which crystal data have been reported include acyl hydrazone derivatives of 2-phenylchroman-4-one and hesperetin. In particular, crystal structures for 2′-[2-(4-fluorophenyl)chroman-4-ylidene]isonicotinohydrazide (Nie et al., 2006) and N-{(±)-[5,7-dihydroxy-2-(3-hydroxy-4-methoxy-phenyl)chroman-4-ylidene]amino}benzamide (Lodyga-Chruscinska et al., 2015) have been reported.
5. Synthesis and crystallization
For the preparation of I, naringenin (653 mg, 2.4 mmol) and 2-(naphthalen-1-yl)acetohydrazide (501 mg, 2.5 mmol) were dissolved in ethanol (10 mL). Acetic acid (2.4 mmol, 137 µL) was added and the resultant solution was heated at reflux for 21 h. The precipitate was isolated via vacuum filtration and recrystallized from ethyl acetate via slow evaporation at room temperature to furnish clear, plate-shaped crystals suitable for X-ray analysis.
For the preparation of II, naringenin (3.000 g, 11.02 mmol) and 4-hydroxybenzohydrazine (2.011 g, 13.22 mmol) were dissolved in ethanol (20 mL). Acetic acid (17.5 mmol, 1.0 mL) was added and the resultant solution was heated at reflux for 48 h. The precipitate was isolated via filtration and recrystallized from ethanol via slow evaporation at room temperature to furnish transparent yellow, plate-shaped crystals suitable for X-ray analysis.
For the preparation of III, 6-methoxyflavanone (381 mg, 1.5 mmol), 2-(naphthalen-1-yl)acetohydrazide (356.8 mg, 1.1 eq, 1.65 mmol), and p-toluenesulfonic acid (29 mg, 0.10 eq, 0.15 mmol) were dissolved in toluene (15mL). The resultant mixture was heated at reflux for 12 h with a Dean–Stark apparatus. The solvent was removed and the crude product was purified on an automated flash system using a normal phase silica gel column with a gradient of hexane:ethyl acetate (70:30 to 0:100). Recrystallization of the purified compound from ethanol via slow evaporation at room temperature furnished yellow, needle-shaped crystals suitable for X-ray analysis.
6. Refinement
Crystal data, data collection and structure . The hydrogen atoms were placed in their geometrically calculated positions and their coordinates refined using the riding model with parent-atom—H lengths of 0.93 Å (CH), 0.98 Å (chiral-CH), 0.96 Å (CH3), 0.97 Å (CH2), 0.86 Å (NH) or 0.82 Å (OH). Isotropic displacement parameters for these atoms were set to 1.2 (CH, NH) or 1.5 (CH3, OH) times Ueq of the parent atom. In II, the positional disorder of the chiral carbon (C8) and phenoxy ring atoms (C10 through C15) refined to a percentage population ratio of 66/34, and that of the solvent (ethanol) molecule to 57/43, necessitating the use of a total of 136 restraints. The idealized Me of the ethanol molecule were refined as rotating group(s): C2_3 and C2_4 (H2A_3 through H2C_4).
details for all three structures are summarized in Table 4
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Supporting information
https://doi.org/10.1107/S2056989023001184/jy2026sup1.cif
contains datablocks I, II, III, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023001184/jy2026Isup2.hkl
Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989023001184/jy2026IIsup3.hkl
Structure factors: contains datablock III. DOI: https://doi.org/10.1107/S2056989023001184/jy2026IIIsup4.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989023001184/jy2026Isup5.mol
Supporting information file. DOI: https://doi.org/10.1107/S2056989023001184/jy2026IIsup6.mol
Supporting information file. DOI: https://doi.org/10.1107/S2056989023001184/jy2026IIIsup7.mol
Supporting information file. DOI: https://doi.org/10.1107/S2056989023001184/jy2026Isup8.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989023001184/jy2026IIsup9.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989023001184/jy2026IIIsup10.cml
hkl file for data_I. DOI: https://doi.org/10.1107/S2056989023001184/jy2026sup11.txt
hkl file for data_II. DOI: https://doi.org/10.1107/S2056989023001184/jy2026sup12.txt
hkl file for data_III. DOI: https://doi.org/10.1107/S2056989023001184/jy2026sup13.txt
RES files for data_block I. DOI: https://doi.org/10.1107/S2056989023001184/jy2026sup14.txt
RES file for data_block II. DOI: https://doi.org/10.1107/S2056989023001184/jy2026sup15.txt
RES file for data_block III. DOI: https://doi.org/10.1107/S2056989023001184/jy2026sup16.txt
matched hkl file for data_III. DOI: https://doi.org/10.1107/S2056989023001184/jy2026sup17.txt
matched hkl file for data_II. DOI: https://doi.org/10.1107/S2056989023001184/jy2026sup18.txt
matched hkl file for data_I. DOI: https://doi.org/10.1107/S2056989023001184/jy2026sup19.txt
SHELX data. DOI: https://doi.org/10.1107/S2056989023001184/jy2026sup20.zip
SHELX data. DOI: https://doi.org/10.1107/S2056989023001184/jy2026sup21.zip
Structure 1 res file. DOI: https://doi.org/10.1107/S2056989023001184/jy2026sup22.txt
Structure I hkl file. DOI: https://doi.org/10.1107/S2056989023001184/jy2026sup23.txt
Structure II res file. DOI: https://doi.org/10.1107/S2056989023001184/jy2026sup24.txt
Structure II hkl file. DOI: https://doi.org/10.1107/S2056989023001184/jy2026sup25.txt
Structure III res file. DOI: https://doi.org/10.1107/S2056989023001184/jy2026sup26.txt
Structure III hkl file. DOI: https://doi.org/10.1107/S2056989023001184/jy2026sup27.txt
For all structures, data collection: CrysAlis PRO 1.171.42.63a (Rigaku OD, 2022); cell
CrysAlis PRO 1.171.42.63a (Rigaku OD, 2022); data reduction: CrysAlis PRO 1.171.42.63a (Rigaku OD, 2022). Program(s) used to solve structure: olex2.solve 1.3-ac4 (Bourhis et al., 2015) for (I). For all structures, program(s) used to refine structure: SHELXL 2018/3 (Sheldrick, 2015); molecular graphics: Olex2 1.3-ac4 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 1.3-ac4 (Dolomanov et al., 2009).C27H22N2O5·C4H8O2 | Z = 2 |
Mr = 542.57 | F(000) = 572 |
Triclinic, P1 | Dx = 1.291 Mg m−3 |
a = 9.2210 (5) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 12.1902 (8) Å | Cell parameters from 7321 reflections |
c = 13.4982 (7) Å | θ = 3.3–75.2° |
α = 94.413 (5)° | µ = 0.76 mm−1 |
β = 95.172 (4)° | T = 293 K |
γ = 111.561 (5)° | Plate, clear colourless |
V = 1395.40 (15) Å3 | 0.12 × 0.1 × 0.02 mm |
ROD, Synergy Custom system, HyPix-Arc 150 diffractometer | 5498 independent reflections |
Radiation source: Rotating-anode X-ray tube, Rigaku (Cu) X-ray Source | 3477 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.034 |
Detector resolution: 10.0000 pixels mm-1 | θmax = 75.9°, θmin = 3.3° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2022) | k = −15→14 |
Tmin = 0.912, Tmax = 1.000 | l = −16→12 |
15709 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.062 | w = 1/[σ2(Fo2) + (0.1145P)2 + 0.0876P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.212 | (Δ/σ)max < 0.001 |
S = 1.09 | Δρmax = 0.50 e Å−3 |
5498 reflections | Δρmin = −0.25 e Å−3 |
404 parameters | Extinction correction: SHELXL-2018/3 (Sheldrick 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
60 restraints | Extinction coefficient: 0.0043 (8) |
Primary atom site location: iterative |
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) | |
O1 | 0.6529 (2) | 0.67088 (14) | 0.64906 (14) | 0.0691 (5) | |
O2 | 0.3755 (3) | 0.32732 (16) | 0.78886 (14) | 0.0732 (6) | |
H2 | 0.357223 | 0.255910 | 0.784880 | 0.110* | |
O3 | 0.6861 (2) | 0.29835 (14) | 0.53395 (12) | 0.0587 (5) | |
H3 | 0.734294 | 0.337833 | 0.492432 | 0.088* | |
O4 | 0.8931 (2) | 1.22094 (14) | 0.63511 (15) | 0.0699 (5) | |
H4 | 0.820055 | 1.232642 | 0.604745 | 0.105* | |
O5 | 0.9167 (2) | 0.35560 (15) | 0.32740 (13) | 0.0676 (5) | |
N1 | 0.8079 (2) | 0.48109 (16) | 0.44746 (14) | 0.0523 (5) | |
N2 | 0.8883 (2) | 0.52798 (17) | 0.37020 (14) | 0.0559 (5) | |
H2A | 0.907953 | 0.600522 | 0.359940 | 0.067* | |
C1 | 0.7675 (3) | 0.54747 (19) | 0.50946 (17) | 0.0504 (5) | |
C2 | 0.6743 (3) | 0.48816 (19) | 0.58533 (16) | 0.0495 (5) | |
C3 | 0.6336 (3) | 0.36660 (19) | 0.59418 (17) | 0.0497 (5) | |
C4 | 0.5359 (3) | 0.3116 (2) | 0.66263 (17) | 0.0556 (6) | |
H4A | 0.510446 | 0.231204 | 0.667796 | 0.067* | |
C5 | 0.4763 (3) | 0.3773 (2) | 0.72333 (18) | 0.0561 (6) | |
C6 | 0.5177 (3) | 0.4979 (2) | 0.71828 (19) | 0.0616 (7) | |
H6 | 0.478794 | 0.541832 | 0.760104 | 0.074* | |
C7 | 0.6165 (3) | 0.5524 (2) | 0.65115 (18) | 0.0547 (6) | |
C8 | 0.7937 (4) | 0.7331 (2) | 0.6102 (2) | 0.0692 (8) | |
H8 | 0.879916 | 0.729332 | 0.656079 | 0.083* | |
C9 | 0.8033 (3) | 0.6775 (2) | 0.50939 (17) | 0.0562 (6) | |
H9A | 0.729095 | 0.689158 | 0.459701 | 0.067* | |
H9B | 0.908012 | 0.716126 | 0.491192 | 0.067* | |
C10 | 0.8150 (4) | 0.8617 (2) | 0.6144 (2) | 0.0618 (7) | |
C11A | 0.941 (4) | 0.942 (2) | 0.6829 (18) | 0.057 (4) | 0.29 (3) |
H11A | 1.009448 | 0.917739 | 0.721640 | 0.068* | 0.29 (3) |
C11B | 0.9501 (17) | 0.9468 (11) | 0.6569 (10) | 0.075 (3) | 0.71 (3) |
H11B | 1.029305 | 0.923893 | 0.684204 | 0.090* | 0.71 (3) |
C12A | 0.957 (3) | 1.061 (2) | 0.6892 (16) | 0.054 (4) | 0.29 (3) |
H12A | 1.032911 | 1.115939 | 0.737333 | 0.065* | 0.29 (3) |
C12B | 0.9790 (14) | 1.0664 (10) | 0.6628 (10) | 0.073 (3) | 0.71 (3) |
H12B | 1.075991 | 1.122273 | 0.691794 | 0.088* | 0.71 (3) |
C13 | 0.8629 (3) | 1.1015 (2) | 0.62542 (18) | 0.0552 (6) | |
C14A | 0.754 (3) | 1.017 (2) | 0.561 (2) | 0.063 (6) | 0.29 (3) |
H14A | 0.716016 | 1.036696 | 0.501339 | 0.076* | 0.29 (3) |
C14B | 0.7203 (11) | 1.0200 (8) | 0.5770 (8) | 0.0591 (17) | 0.71 (3) |
H14B | 0.637252 | 1.042150 | 0.555969 | 0.071* | 0.71 (3) |
C15A | 0.696 (4) | 0.897 (3) | 0.583 (2) | 0.060 (5) | 0.29 (3) |
H15A | 0.590208 | 0.848653 | 0.577167 | 0.072* | 0.29 (3) |
C15B | 0.7098 (16) | 0.8998 (12) | 0.5617 (11) | 0.074 (3) | 0.71 (3) |
H15B | 0.630181 | 0.845746 | 0.515181 | 0.089* | 0.71 (3) |
C16 | 0.9357 (3) | 0.4563 (2) | 0.31054 (17) | 0.0557 (6) | |
C17 | 1.0111 (3) | 0.5114 (2) | 0.22271 (18) | 0.0657 (7) | |
H17A | 1.113605 | 0.506219 | 0.223075 | 0.079* | |
H17B | 1.025891 | 0.594748 | 0.228703 | 0.079* | |
C18 | 0.9101 (3) | 0.4491 (2) | 0.12479 (18) | 0.0599 (6) | |
C19 | 0.8009 (4) | 0.4899 (3) | 0.0847 (2) | 0.0792 (9) | |
H19 | 0.787197 | 0.554213 | 0.118333 | 0.095* | |
C20 | 0.7074 (4) | 0.4338 (4) | −0.0093 (3) | 0.0987 (12) | |
H20 | 0.632133 | 0.460805 | −0.036553 | 0.118* | |
C21 | 0.7296 (5) | 0.3416 (4) | −0.0578 (3) | 0.0965 (11) | |
H21 | 0.669012 | 0.306306 | −0.118958 | 0.116* | |
C22 | 0.8380 (4) | 0.2977 (3) | −0.0206 (2) | 0.0786 (9) | |
C23 | 0.9276 (3) | 0.3499 (2) | 0.07340 (18) | 0.0619 (7) | |
C24 | 1.0342 (4) | 0.3000 (3) | 0.1086 (2) | 0.0826 (9) | |
H24 | 1.094272 | 0.331436 | 0.170610 | 0.099* | |
C25 | 1.0540 (6) | 0.2075 (4) | 0.0561 (3) | 0.1191 (15) | |
H25 | 1.125586 | 0.176640 | 0.082417 | 0.143* | |
C26 | 0.9669 (7) | 0.1600 (4) | −0.0366 (4) | 0.1339 (18) | |
H26 | 0.982094 | 0.098063 | −0.073114 | 0.161* | |
C27 | 0.8617 (5) | 0.2017 (4) | −0.0744 (3) | 0.1051 (13) | |
H27 | 0.803198 | 0.167824 | −0.136491 | 0.126* | |
O6 | 0.3415 (3) | 0.09561 (19) | 0.78449 (17) | 0.0915 (7) | |
O7 | 0.3890 (3) | −0.04819 (19) | 0.85469 (17) | 0.0935 (7) | |
C28 | 0.3659 (5) | 0.1020 (3) | 0.9623 (3) | 0.1020 (12) | |
H28A | 0.358033 | 0.178276 | 0.961757 | 0.153* | |
H28B | 0.462489 | 0.110491 | 1.001444 | 0.153* | |
H28C | 0.278770 | 0.049573 | 0.991100 | 0.153* | |
C29 | 0.3634 (4) | 0.0516 (2) | 0.8580 (2) | 0.0724 (8) | |
C30 | 0.3861 (6) | −0.1082 (3) | 0.7563 (3) | 0.1097 (13) | |
H30A | 0.449610 | −0.051887 | 0.715369 | 0.132* | |
H30B | 0.279194 | −0.143361 | 0.722555 | 0.132* | |
C31 | 0.4493 (5) | −0.2009 (4) | 0.7716 (3) | 0.1133 (13) | |
H31A | 0.432660 | −0.250460 | 0.709538 | 0.170* | |
H31B | 0.396736 | −0.248231 | 0.820839 | 0.170* | |
H31C | 0.559927 | −0.164463 | 0.794426 | 0.170* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0919 (14) | 0.0403 (9) | 0.0881 (12) | 0.0322 (9) | 0.0401 (11) | 0.0149 (8) |
O2 | 0.0844 (14) | 0.0609 (11) | 0.0837 (12) | 0.0294 (11) | 0.0366 (11) | 0.0241 (10) |
O3 | 0.0746 (12) | 0.0409 (8) | 0.0697 (11) | 0.0291 (8) | 0.0206 (9) | 0.0091 (7) |
O4 | 0.0734 (13) | 0.0367 (9) | 0.0982 (14) | 0.0202 (9) | 0.0059 (10) | 0.0081 (8) |
O5 | 0.0899 (14) | 0.0518 (10) | 0.0704 (11) | 0.0340 (10) | 0.0232 (10) | 0.0093 (8) |
N1 | 0.0621 (13) | 0.0438 (10) | 0.0561 (11) | 0.0235 (9) | 0.0148 (9) | 0.0089 (8) |
N2 | 0.0724 (14) | 0.0402 (10) | 0.0598 (11) | 0.0232 (10) | 0.0201 (10) | 0.0102 (8) |
C1 | 0.0600 (15) | 0.0398 (11) | 0.0555 (12) | 0.0230 (11) | 0.0095 (11) | 0.0074 (9) |
C2 | 0.0575 (14) | 0.0393 (11) | 0.0571 (12) | 0.0233 (10) | 0.0106 (11) | 0.0073 (9) |
C3 | 0.0532 (14) | 0.0405 (11) | 0.0589 (13) | 0.0220 (10) | 0.0069 (11) | 0.0057 (9) |
C4 | 0.0626 (16) | 0.0428 (12) | 0.0643 (14) | 0.0220 (11) | 0.0094 (12) | 0.0115 (10) |
C5 | 0.0628 (16) | 0.0511 (13) | 0.0609 (14) | 0.0257 (12) | 0.0145 (12) | 0.0146 (11) |
C6 | 0.0747 (18) | 0.0519 (14) | 0.0676 (15) | 0.0308 (13) | 0.0239 (13) | 0.0097 (11) |
C7 | 0.0654 (16) | 0.0417 (12) | 0.0648 (14) | 0.0272 (11) | 0.0138 (12) | 0.0102 (10) |
C8 | 0.089 (2) | 0.0471 (14) | 0.0797 (17) | 0.0298 (14) | 0.0289 (15) | 0.0120 (12) |
C9 | 0.0717 (17) | 0.0420 (12) | 0.0617 (14) | 0.0266 (12) | 0.0160 (12) | 0.0114 (10) |
C10 | 0.0781 (19) | 0.0458 (13) | 0.0735 (16) | 0.0326 (14) | 0.0247 (14) | 0.0125 (12) |
C11A | 0.076 (8) | 0.048 (7) | 0.049 (7) | 0.029 (5) | −0.004 (6) | 0.003 (5) |
C11B | 0.085 (4) | 0.061 (3) | 0.090 (6) | 0.040 (3) | 0.004 (5) | 0.019 (4) |
C12A | 0.068 (8) | 0.047 (6) | 0.054 (7) | 0.030 (6) | 0.001 (6) | 0.005 (5) |
C12B | 0.070 (4) | 0.051 (3) | 0.096 (6) | 0.023 (3) | 0.000 (4) | 0.007 (4) |
C13 | 0.0627 (16) | 0.0356 (11) | 0.0691 (15) | 0.0194 (11) | 0.0127 (12) | 0.0069 (10) |
C14A | 0.063 (9) | 0.064 (7) | 0.075 (8) | 0.040 (6) | 0.002 (6) | 0.006 (6) |
C14B | 0.051 (3) | 0.043 (2) | 0.087 (4) | 0.023 (2) | 0.011 (3) | 0.001 (2) |
C15A | 0.055 (7) | 0.049 (7) | 0.062 (8) | 0.004 (5) | 0.009 (6) | −0.002 (6) |
C15B | 0.087 (5) | 0.045 (3) | 0.081 (6) | 0.018 (3) | 0.002 (4) | −0.003 (3) |
C16 | 0.0619 (16) | 0.0452 (12) | 0.0579 (13) | 0.0180 (11) | 0.0104 (11) | 0.0015 (10) |
C17 | 0.0754 (19) | 0.0553 (15) | 0.0600 (15) | 0.0158 (13) | 0.0196 (13) | 0.0017 (11) |
C18 | 0.0638 (16) | 0.0591 (15) | 0.0588 (14) | 0.0209 (13) | 0.0206 (12) | 0.0158 (11) |
C19 | 0.081 (2) | 0.082 (2) | 0.087 (2) | 0.0371 (17) | 0.0281 (18) | 0.0308 (16) |
C20 | 0.064 (2) | 0.127 (3) | 0.108 (3) | 0.031 (2) | 0.009 (2) | 0.055 (2) |
C21 | 0.085 (3) | 0.111 (3) | 0.075 (2) | 0.013 (2) | 0.0124 (18) | 0.019 (2) |
C22 | 0.078 (2) | 0.079 (2) | 0.0632 (17) | 0.0101 (17) | 0.0154 (15) | 0.0095 (15) |
C23 | 0.0668 (17) | 0.0615 (15) | 0.0526 (13) | 0.0161 (13) | 0.0172 (12) | 0.0093 (11) |
C24 | 0.103 (3) | 0.084 (2) | 0.0773 (18) | 0.050 (2) | 0.0276 (17) | 0.0138 (16) |
C25 | 0.170 (4) | 0.117 (3) | 0.109 (3) | 0.091 (3) | 0.051 (3) | 0.015 (3) |
C26 | 0.189 (6) | 0.103 (3) | 0.118 (4) | 0.060 (4) | 0.056 (4) | −0.006 (3) |
C27 | 0.127 (4) | 0.089 (3) | 0.071 (2) | 0.011 (2) | 0.023 (2) | −0.0125 (18) |
O6 | 0.1160 (19) | 0.0635 (13) | 0.1004 (15) | 0.0374 (13) | 0.0119 (13) | 0.0261 (11) |
O7 | 0.131 (2) | 0.0734 (14) | 0.0982 (15) | 0.0582 (14) | 0.0304 (14) | 0.0243 (11) |
C28 | 0.134 (3) | 0.098 (3) | 0.099 (2) | 0.064 (3) | 0.043 (2) | 0.0249 (19) |
C29 | 0.0725 (19) | 0.0546 (15) | 0.096 (2) | 0.0243 (14) | 0.0256 (16) | 0.0242 (14) |
C30 | 0.150 (4) | 0.080 (2) | 0.106 (3) | 0.053 (3) | 0.015 (3) | 0.000 (2) |
C31 | 0.131 (4) | 0.100 (3) | 0.129 (3) | 0.065 (3) | 0.035 (3) | 0.004 (2) |
O1—C7 | 1.361 (3) | C14A—H14A | 0.9300 |
O1—C8 | 1.413 (3) | C14A—C15A | 1.43 (3) |
O2—H2 | 0.8200 | C14B—H14B | 0.9300 |
O2—C5 | 1.353 (3) | C14B—C15B | 1.430 (14) |
O3—H3 | 0.8200 | C15A—H15A | 0.9300 |
O3—C3 | 1.361 (3) | C15B—H15B | 0.9300 |
O4—H4 | 0.8200 | C16—C17 | 1.506 (3) |
O4—C13 | 1.371 (3) | C17—H17A | 0.9700 |
O5—C16 | 1.217 (3) | C17—H17B | 0.9700 |
N1—N2 | 1.372 (3) | C17—C18 | 1.515 (4) |
N1—C1 | 1.291 (3) | C18—C19 | 1.367 (4) |
N2—H2A | 0.8600 | C18—C23 | 1.415 (4) |
N2—C16 | 1.356 (3) | C19—H19 | 0.9300 |
C1—C2 | 1.458 (3) | C19—C20 | 1.434 (5) |
C1—C9 | 1.496 (3) | C20—H20 | 0.9300 |
C2—C3 | 1.406 (3) | C20—C21 | 1.346 (5) |
C2—C7 | 1.404 (3) | C21—H21 | 0.9300 |
C3—C4 | 1.384 (3) | C21—C22 | 1.372 (5) |
C4—H4A | 0.9300 | C22—C23 | 1.413 (4) |
C4—C5 | 1.385 (3) | C22—C27 | 1.426 (5) |
C5—C6 | 1.386 (3) | C23—C24 | 1.400 (4) |
C6—H6 | 0.9300 | C24—H24 | 0.9300 |
C6—C7 | 1.374 (3) | C24—C25 | 1.363 (4) |
C8—H8 | 0.9800 | C25—H25 | 0.9300 |
C8—C9 | 1.497 (3) | C25—C26 | 1.383 (7) |
C8—C10 | 1.502 (3) | C26—H26 | 0.9300 |
C9—H9A | 0.9700 | C26—C27 | 1.331 (6) |
C9—H9B | 0.9700 | C27—H27 | 0.9300 |
C10—C11A | 1.41 (3) | O6—C29 | 1.199 (3) |
C10—C11B | 1.337 (13) | O7—C29 | 1.320 (3) |
C10—C15A | 1.36 (3) | O7—C30 | 1.459 (4) |
C10—C15B | 1.386 (13) | C28—H28A | 0.9600 |
C11A—H11A | 0.9300 | C28—H28B | 0.9600 |
C11A—C12A | 1.40 (3) | C28—H28C | 0.9600 |
C11B—H11B | 0.9300 | C28—C29 | 1.487 (5) |
C11B—C12B | 1.377 (14) | C30—H30A | 0.9700 |
C12A—H12A | 0.9300 | C30—H30B | 0.9700 |
C12A—C13 | 1.41 (2) | C30—C31 | 1.469 (5) |
C12B—H12B | 0.9300 | C31—H31A | 0.9600 |
C12B—C13 | 1.362 (12) | C31—H31B | 0.9600 |
C13—C14A | 1.33 (2) | C31—H31C | 0.9600 |
C13—C14B | 1.388 (9) | ||
C7—O1—C8 | 115.96 (18) | C13—C14B—C15B | 115.5 (9) |
C5—O2—H2 | 109.5 | C15B—C14B—H14B | 122.2 |
C3—O3—H3 | 109.5 | C10—C15A—C14A | 112 (2) |
C13—O4—H4 | 109.5 | C10—C15A—H15A | 124.1 |
C1—N1—N2 | 120.20 (19) | C14A—C15A—H15A | 124.1 |
N1—N2—H2A | 121.1 | C10—C15B—C14B | 121.7 (11) |
C16—N2—N1 | 117.90 (19) | C10—C15B—H15B | 119.1 |
C16—N2—H2A | 121.1 | C14B—C15B—H15B | 119.1 |
N1—C1—C2 | 116.19 (19) | O5—C16—N2 | 121.9 (2) |
N1—C1—C9 | 126.6 (2) | O5—C16—C17 | 123.7 (2) |
C2—C1—C9 | 117.23 (18) | N2—C16—C17 | 114.5 (2) |
C3—C2—C1 | 122.97 (18) | C16—C17—H17A | 109.4 |
C7—C2—C1 | 119.7 (2) | C16—C17—H17B | 109.4 |
C7—C2—C3 | 117.3 (2) | C16—C17—C18 | 111.0 (2) |
O3—C3—C2 | 121.0 (2) | H17A—C17—H17B | 108.0 |
O3—C3—C4 | 117.68 (19) | C18—C17—H17A | 109.4 |
C4—C3—C2 | 121.30 (19) | C18—C17—H17B | 109.4 |
C3—C4—H4A | 120.3 | C19—C18—C17 | 119.4 (3) |
C3—C4—C5 | 119.5 (2) | C19—C18—C23 | 119.2 (3) |
C5—C4—H4A | 120.3 | C23—C18—C17 | 121.3 (2) |
O2—C5—C4 | 122.1 (2) | C18—C19—H19 | 120.0 |
O2—C5—C6 | 117.4 (2) | C18—C19—C20 | 120.1 (3) |
C4—C5—C6 | 120.6 (2) | C20—C19—H19 | 120.0 |
C5—C6—H6 | 120.2 | C19—C20—H20 | 120.3 |
C7—C6—C5 | 119.7 (2) | C21—C20—C19 | 119.3 (3) |
C7—C6—H6 | 120.2 | C21—C20—H20 | 120.3 |
O1—C7—C2 | 121.2 (2) | C20—C21—H21 | 118.6 |
O1—C7—C6 | 117.2 (2) | C20—C21—C22 | 122.7 (3) |
C6—C7—C2 | 121.6 (2) | C22—C21—H21 | 118.6 |
O1—C8—H8 | 106.8 | C21—C22—C23 | 118.5 (3) |
O1—C8—C9 | 113.1 (2) | C21—C22—C27 | 121.6 (3) |
O1—C8—C10 | 108.5 (2) | C23—C22—C27 | 119.9 (3) |
C9—C8—H8 | 106.8 | C22—C23—C18 | 120.0 (3) |
C9—C8—C10 | 114.5 (2) | C24—C23—C18 | 123.8 (3) |
C10—C8—H8 | 106.8 | C24—C23—C22 | 116.1 (3) |
C1—C9—C8 | 111.10 (19) | C23—C24—H24 | 118.5 |
C1—C9—H9A | 109.4 | C25—C24—C23 | 123.0 (3) |
C1—C9—H9B | 109.4 | C25—C24—H24 | 118.5 |
C8—C9—H9A | 109.4 | C24—C25—H25 | 120.2 |
C8—C9—H9B | 109.4 | C24—C25—C26 | 119.5 (4) |
H9A—C9—H9B | 108.0 | C26—C25—H25 | 120.2 |
C11A—C10—C8 | 116.4 (14) | C25—C26—H26 | 119.5 |
C11B—C10—C8 | 120.6 (7) | C27—C26—C25 | 120.9 (4) |
C11B—C10—C15B | 116.0 (9) | C27—C26—H26 | 119.5 |
C15A—C10—C8 | 122.4 (14) | C22—C27—H27 | 119.7 |
C15A—C10—C11A | 118 (2) | C26—C27—C22 | 120.6 (4) |
C15B—C10—C8 | 122.7 (6) | C26—C27—H27 | 119.7 |
C10—C11A—H11A | 121.9 | C29—O7—C30 | 117.7 (3) |
C12A—C11A—C10 | 116 (3) | H28A—C28—H28B | 109.5 |
C12A—C11A—H11A | 121.9 | H28A—C28—H28C | 109.5 |
C10—C11B—H11B | 118.0 | H28B—C28—H28C | 109.5 |
C10—C11B—C12B | 124.0 (12) | C29—C28—H28A | 109.5 |
C12B—C11B—H11B | 118.0 | C29—C28—H28B | 109.5 |
C11A—C12A—H12A | 118.7 | C29—C28—H28C | 109.5 |
C11A—C12A—C13 | 123 (2) | O6—C29—O7 | 123.1 (3) |
C13—C12A—H12A | 118.7 | O6—C29—C28 | 124.7 (3) |
C11B—C12B—H12B | 120.6 | O7—C29—C28 | 112.2 (3) |
C13—C12B—C11B | 118.8 (11) | O7—C30—H30A | 110.2 |
C13—C12B—H12B | 120.6 | O7—C30—H30B | 110.2 |
O4—C13—C12A | 117.7 (11) | O7—C30—C31 | 107.6 (3) |
O4—C13—C14B | 120.9 (5) | H30A—C30—H30B | 108.5 |
C12B—C13—O4 | 117.6 (5) | C31—C30—H30A | 110.2 |
C12B—C13—C14B | 121.5 (7) | C31—C30—H30B | 110.2 |
C14A—C13—O4 | 127.3 (11) | C30—C31—H31A | 109.5 |
C14A—C13—C12A | 115.0 (16) | C30—C31—H31B | 109.5 |
C13—C14A—H14A | 120.1 | C30—C31—H31C | 109.5 |
C13—C14A—C15A | 120 (2) | H31A—C31—H31B | 109.5 |
C15A—C14A—H14A | 120.1 | H31A—C31—H31C | 109.5 |
C13—C14B—H14B | 122.2 | H31B—C31—H31C | 109.5 |
O1—C8—C9—C1 | −50.2 (3) | C9—C8—C10—C11B | −104.4 (7) |
O1—C8—C10—C11A | 111.6 (14) | C9—C8—C10—C15A | 81.1 (15) |
O1—C8—C10—C11B | 128.3 (7) | C9—C8—C10—C15B | 65.0 (8) |
O1—C8—C10—C15A | −46.3 (16) | C10—C8—C9—C1 | −175.2 (2) |
O1—C8—C10—C15B | −62.4 (8) | C10—C11A—C12A—C13 | −5 (3) |
O2—C5—C6—C7 | −178.3 (2) | C10—C11B—C12B—C13 | 1.6 (14) |
O3—C3—C4—C5 | −178.2 (2) | C11A—C10—C15A—C14A | 43 (3) |
O4—C13—C14A—C15A | −156 (2) | C11A—C12A—C13—O4 | −177.2 (19) |
O4—C13—C14B—C15B | 173.1 (9) | C11A—C12A—C13—C14A | 2 (3) |
O5—C16—C17—C18 | 66.2 (4) | C11B—C10—C15B—C14B | −19 (2) |
N1—N2—C16—O5 | −4.2 (4) | C11B—C12B—C13—O4 | 178.0 (7) |
N1—N2—C16—C17 | 175.2 (2) | C11B—C12B—C13—C14B | −3.6 (11) |
N1—C1—C2—C3 | 2.0 (4) | C12A—C13—C14A—C15A | 25 (3) |
N1—C1—C2—C7 | −175.6 (2) | C12B—C13—C14B—C15B | −5.3 (12) |
N1—C1—C9—C8 | −158.5 (3) | C13—C14A—C15A—C10 | −48 (4) |
N2—N1—C1—C2 | 176.4 (2) | C13—C14B—C15B—C10 | 17 (2) |
N2—N1—C1—C9 | −2.0 (4) | C15A—C10—C11A—C12A | −19 (3) |
N2—C16—C17—C18 | −113.2 (3) | C15B—C10—C11B—C12B | 9.3 (15) |
C1—N1—N2—C16 | 176.4 (2) | C16—C17—C18—C19 | 91.2 (3) |
C1—C2—C3—O3 | 3.0 (4) | C16—C17—C18—C23 | −89.4 (3) |
C1—C2—C3—C4 | −175.5 (2) | C17—C18—C19—C20 | 178.3 (3) |
C1—C2—C7—O1 | −3.5 (4) | C17—C18—C23—C22 | −176.4 (2) |
C1—C2—C7—C6 | 174.6 (2) | C17—C18—C23—C24 | 1.5 (4) |
C2—C1—C9—C8 | 23.1 (3) | C18—C19—C20—C21 | −0.7 (5) |
C2—C3—C4—C5 | 0.3 (4) | C18—C23—C24—C25 | −177.2 (3) |
C3—C2—C7—O1 | 178.6 (2) | C19—C18—C23—C22 | 3.0 (4) |
C3—C2—C7—C6 | −3.2 (4) | C19—C18—C23—C24 | −179.1 (3) |
C3—C4—C5—O2 | 177.4 (2) | C19—C20—C21—C22 | 0.6 (5) |
C3—C4—C5—C6 | −2.1 (4) | C20—C21—C22—C23 | 1.3 (5) |
C4—C5—C6—C7 | 1.2 (4) | C20—C21—C22—C27 | −178.6 (3) |
C5—C6—C7—O1 | 179.8 (2) | C21—C22—C23—C18 | −3.1 (4) |
C5—C6—C7—C2 | 1.5 (4) | C21—C22—C23—C24 | 178.8 (3) |
C7—O1—C8—C9 | 52.2 (3) | C21—C22—C27—C26 | −179.6 (4) |
C7—O1—C8—C10 | −179.6 (2) | C22—C23—C24—C25 | 0.8 (5) |
C7—C2—C3—O3 | −179.3 (2) | C23—C18—C19—C20 | −1.1 (4) |
C7—C2—C3—C4 | 2.3 (4) | C23—C22—C27—C26 | 0.5 (6) |
C8—O1—C7—C2 | −24.6 (4) | C23—C24—C25—C26 | 0.5 (6) |
C8—O1—C7—C6 | 157.2 (2) | C24—C25—C26—C27 | −1.4 (7) |
C8—C10—C11A—C12A | −177.8 (16) | C25—C26—C27—C22 | 0.9 (7) |
C8—C10—C11B—C12B | 179.4 (7) | C27—C22—C23—C18 | 176.8 (3) |
C8—C10—C15A—C14A | −159.4 (18) | C27—C22—C23—C24 | −1.3 (4) |
C8—C10—C15B—C14B | 171.4 (10) | C29—O7—C30—C31 | 168.3 (3) |
C9—C1—C2—C3 | −179.4 (2) | C30—O7—C29—O6 | −1.6 (5) |
C9—C1—C2—C7 | 2.9 (3) | C30—O7—C29—C28 | 178.6 (3) |
C9—C8—C10—C11A | −121.0 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···N1 | 0.82 | 1.80 | 2.527 (2) | 147 |
O2—H2···O6 | 0.82 | 1.91 | 2.720 (3) | 173 |
O4—H4···O3i | 0.82 | 1.93 | 2.730 (3) | 166 |
C9—H9B···O4ii | 0.97 | 2.57 | 3.461 (3) | 153 |
Symmetry codes: (i) x, y+1, z; (ii) −x+2, −y+2, −z+1. |
C22H18N2O6·C2H6O | Z = 2 |
Mr = 452.45 | F(000) = 476 |
Triclinic, P1 | Dx = 1.289 Mg m−3 |
a = 10.0964 (9) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 10.1570 (8) Å | Cell parameters from 5399 reflections |
c = 12.3628 (10) Å | θ = 3.9–76.0° |
α = 84.557 (7)° | µ = 0.80 mm−1 |
β = 68.169 (8)° | T = 293 K |
γ = 82.529 (7)° | Plate, yellow |
V = 1165.39 (18) Å3 | 0.18 × 0.16 × 0.04 mm |
ROD, Synergy Custom system, HyPix-Arc 150 diffractometer | 4585 independent reflections |
Radiation source: Rotating-anode X-ray tube, Rigaku (Cu) X-ray Source | 2642 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.045 |
Detector resolution: 10.0000 pixels mm-1 | θmax = 79.0°, θmin = 3.9° |
ω scans | h = −12→11 |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2022) | k = −11→12 |
Tmin = 0.660, Tmax = 1.000 | l = −15→14 |
12522 measured reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.086 | w = 1/[σ2(Fo2) + (0.1916P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.301 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.45 e Å−3 |
4585 reflections | Δρmin = −0.27 e Å−3 |
405 parameters | Extinction correction: SHELXL-2018/3 (Sheldrick 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
136 restraints | Extinction coefficient: 0.015 (3) |
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) | |
O1 | −0.1351 (2) | 0.6849 (2) | 0.79739 (19) | 0.0754 (7) | |
O2 | −0.3070 (2) | 0.4492 (2) | 0.5747 (2) | 0.0785 (7) | |
H2 | −0.342557 | 0.411258 | 0.638824 | 0.118* | |
O3 | 0.0348 (2) | 0.7463 (2) | 0.37844 (18) | 0.0724 (6) | |
H3 | 0.085010 | 0.796329 | 0.390234 | 0.109* | |
O5 | 0.3098 (3) | 0.9705 (2) | 0.3030 (2) | 0.0837 (7) | |
O6 | 0.6730 (3) | 1.3952 (3) | 0.3686 (2) | 0.0925 (8) | |
H6 | 0.640291 | 1.442748 | 0.424580 | 0.139* | |
N1 | 0.1291 (3) | 0.8729 (2) | 0.4979 (2) | 0.0644 (7) | |
N2 | 0.2153 (3) | 0.9675 (2) | 0.4986 (2) | 0.0654 (7) | |
H2A | 0.211270 | 0.997485 | 0.562629 | 0.079* | |
C1 | 0.0487 (3) | 0.8194 (3) | 0.5956 (3) | 0.0607 (7) | |
C2 | −0.0431 (3) | 0.7220 (3) | 0.5882 (3) | 0.0610 (7) | |
C3 | −0.0481 (3) | 0.6899 (3) | 0.4820 (3) | 0.0609 (8) | |
C4 | −0.1388 (3) | 0.6004 (3) | 0.4786 (3) | 0.0639 (8) | |
H4 | −0.144130 | 0.582551 | 0.407948 | 0.077* | |
C5 | −0.2211 (3) | 0.5383 (3) | 0.5811 (3) | 0.0654 (8) | |
C6 | −0.2188 (3) | 0.5665 (3) | 0.6873 (3) | 0.0682 (8) | |
H6A | −0.275641 | 0.524598 | 0.756009 | 0.082* | |
C7 | −0.1302 (3) | 0.6585 (3) | 0.6892 (3) | 0.0643 (8) | |
C9 | 0.0375 (4) | 0.8466 (4) | 0.7136 (3) | 0.0741 (9) | |
H9AA | 0.045689 | 0.940341 | 0.715850 | 0.089* | 0.340 (11) |
H9AB | 0.117221 | 0.796585 | 0.729797 | 0.089* | 0.340 (11) |
H9BC | 0.130296 | 0.866285 | 0.710629 | 0.089* | 0.660 (11) |
H9BD | −0.029867 | 0.924754 | 0.739493 | 0.089* | 0.660 (11) |
O4_1 | −0.106 (5) | 0.864 (3) | 1.260 (2) | 0.073 (5) | 0.340 (11) |
H4_1 | −0.030662 | 0.825179 | 1.262161 | 0.110* | 0.340 (11) |
C8_1 | −0.0995 (14) | 0.8119 (11) | 0.8069 (7) | 0.066 (3) | 0.340 (11) |
H8_1 | −0.176753 | 0.877540 | 0.800365 | 0.079* | 0.340 (11) |
C10_1 | −0.097 (2) | 0.8167 (15) | 0.9282 (10) | 0.061 (3) | 0.340 (11) |
C11_1 | −0.175 (2) | 0.9296 (17) | 0.9914 (13) | 0.070 (3) | 0.340 (11) |
H11_1 | −0.225729 | 0.993774 | 0.958569 | 0.084* | 0.340 (11) |
C12_1 | −0.176 (3) | 0.943 (2) | 1.1033 (17) | 0.077 (4) | 0.340 (11) |
H12_1 | −0.209873 | 1.023414 | 1.139562 | 0.092* | 0.340 (11) |
C13_1 | −0.1256 (16) | 0.8330 (19) | 1.1593 (13) | 0.056 (3) | 0.340 (11) |
C14_1 | −0.039 (2) | 0.730 (2) | 1.0937 (16) | 0.080 (5) | 0.340 (11) |
H14_1 | 0.009772 | 0.665175 | 1.126783 | 0.096* | 0.340 (11) |
C15_1 | −0.026 (2) | 0.7250 (18) | 0.9820 (14) | 0.076 (4) | 0.340 (11) |
H15_1 | 0.034812 | 0.655947 | 0.939016 | 0.092* | 0.340 (11) |
O4_2 | −0.135 (2) | 0.8700 (16) | 1.2634 (11) | 0.077 (3) | 0.660 (11) |
H4_2 | −0.096223 | 0.813666 | 1.297414 | 0.115* | 0.660 (11) |
C8_2 | −0.0097 (7) | 0.7352 (7) | 0.7987 (4) | 0.0706 (19) | 0.660 (11) |
H8_2 | 0.068019 | 0.662710 | 0.777363 | 0.085* | 0.660 (11) |
C10_2 | −0.0381 (10) | 0.7645 (10) | 0.9230 (6) | 0.071 (2) | 0.660 (11) |
C11_2 | −0.1351 (10) | 0.8742 (10) | 0.9700 (7) | 0.076 (2) | 0.660 (11) |
H11_2 | −0.178298 | 0.925612 | 0.923456 | 0.092* | 0.660 (11) |
C12_2 | −0.1690 (17) | 0.9089 (12) | 1.0835 (10) | 0.083 (3) | 0.660 (11) |
H12_2 | −0.243121 | 0.974346 | 1.116940 | 0.099* | 0.660 (11) |
C13_2 | −0.0882 (10) | 0.8423 (11) | 1.1457 (8) | 0.064 (2) | 0.660 (11) |
C14_2 | 0.0007 (13) | 0.7302 (12) | 1.1015 (9) | 0.078 (2) | 0.660 (11) |
H14_2 | 0.043577 | 0.677733 | 1.147780 | 0.094* | 0.660 (11) |
C15_2 | 0.0274 (9) | 0.6940 (9) | 0.9912 (7) | 0.078 (2) | 0.660 (11) |
H15_2 | 0.091550 | 0.619884 | 0.962366 | 0.093* | 0.660 (11) |
C16_2 | 0.3063 (3) | 1.0107 (3) | 0.3936 (3) | 0.0636 (8) | |
C17_2 | 0.4023 (3) | 1.1118 (3) | 0.3940 (3) | 0.0608 (7) | |
C18_2 | 0.4883 (3) | 1.1626 (3) | 0.2872 (3) | 0.0723 (9) | |
H18_2 | 0.485608 | 1.132852 | 0.219239 | 0.087* | |
C19_2 | 0.5787 (4) | 1.2575 (4) | 0.2797 (3) | 0.0819 (10) | |
H19_2 | 0.636572 | 1.291323 | 0.207324 | 0.098* | |
C20_2 | 0.5820 (3) | 1.3016 (3) | 0.3814 (3) | 0.0707 (9) | |
C21_2 | 0.4985 (3) | 1.2513 (3) | 0.4867 (3) | 0.0693 (8) | |
H21_2 | 0.501184 | 1.281219 | 0.554621 | 0.083* | |
C22_2 | 0.4093 (3) | 1.1559 (3) | 0.4939 (3) | 0.0659 (8) | |
H22_2 | 0.353493 | 1.121001 | 0.566623 | 0.079* | |
O1_3 | −0.388 (2) | 1.274 (2) | 0.7634 (16) | 0.091 (4) | 0.433 (11) |
H1_3 | −0.340646 | 1.201827 | 0.758789 | 0.136* | 0.433 (11) |
C1_3 | −0.5178 (19) | 1.2716 (16) | 0.8636 (15) | 0.098 (4) | 0.433 (11) |
H1A_3 | −0.494641 | 1.243379 | 0.932237 | 0.117* | 0.433 (11) |
H1B_3 | −0.575177 | 1.207245 | 0.853981 | 0.117* | 0.433 (11) |
C2_3 | −0.6057 (13) | 1.4090 (11) | 0.8819 (13) | 0.143 (6) | 0.433 (11) |
H2A_3 | −0.596826 | 1.450423 | 0.806772 | 0.214* | 0.433 (11) |
H2B_3 | −0.577666 | 1.466963 | 0.924742 | 0.214* | 0.433 (11) |
H2C_3 | −0.703526 | 1.391903 | 0.924062 | 0.214* | 0.433 (11) |
O1_4 | −0.412 (2) | 1.3022 (18) | 0.7513 (12) | 0.106 (4) | 0.567 (11) |
H1_4 | −0.350775 | 1.242391 | 0.755089 | 0.159* | 0.567 (11) |
C1_4 | −0.527 (2) | 1.313 (2) | 0.8644 (15) | 0.163 (8) | 0.567 (11) |
H1A_4 | −0.609437 | 1.275514 | 0.862817 | 0.196* | 0.567 (11) |
H1B_4 | −0.554448 | 1.406173 | 0.881159 | 0.196* | 0.567 (11) |
C2_4 | −0.4798 (13) | 1.2400 (19) | 0.9615 (9) | 0.206 (8) | 0.567 (11) |
H2A_4 | −0.447910 | 1.148451 | 0.944346 | 0.310* | 0.567 (11) |
H2B_4 | −0.556780 | 1.244951 | 1.036036 | 0.310* | 0.567 (11) |
H2C_4 | −0.401730 | 1.283391 | 0.963206 | 0.310* | 0.567 (11) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0832 (14) | 0.0856 (15) | 0.0645 (14) | −0.0407 (12) | −0.0238 (10) | −0.0078 (11) |
O2 | 0.0804 (14) | 0.0765 (14) | 0.0888 (16) | −0.0392 (11) | −0.0314 (13) | −0.0090 (12) |
O3 | 0.0789 (14) | 0.0811 (15) | 0.0653 (13) | −0.0354 (11) | −0.0278 (10) | 0.0010 (11) |
O5 | 0.1085 (17) | 0.0820 (15) | 0.0691 (15) | −0.0476 (13) | −0.0290 (12) | −0.0070 (11) |
O6 | 0.0878 (16) | 0.0978 (19) | 0.099 (2) | −0.0569 (14) | −0.0259 (13) | −0.0063 (14) |
N1 | 0.0650 (14) | 0.0629 (15) | 0.0726 (17) | −0.0284 (11) | −0.0269 (12) | 0.0000 (12) |
N2 | 0.0682 (15) | 0.0660 (15) | 0.0703 (16) | −0.0289 (12) | −0.0270 (12) | −0.0056 (12) |
C1 | 0.0607 (16) | 0.0604 (17) | 0.0678 (18) | −0.0188 (13) | −0.0266 (13) | −0.0051 (13) |
C2 | 0.0598 (16) | 0.0607 (17) | 0.0676 (19) | −0.0216 (13) | −0.0239 (13) | −0.0037 (14) |
C3 | 0.0626 (16) | 0.0604 (17) | 0.0646 (18) | −0.0175 (13) | −0.0252 (13) | −0.0030 (13) |
C4 | 0.0621 (16) | 0.0664 (18) | 0.0709 (19) | −0.0189 (14) | −0.0282 (14) | −0.0068 (15) |
C5 | 0.0598 (16) | 0.0637 (18) | 0.080 (2) | −0.0207 (13) | −0.0266 (14) | −0.0121 (15) |
C6 | 0.0642 (17) | 0.0693 (19) | 0.072 (2) | −0.0276 (14) | −0.0191 (14) | −0.0037 (15) |
C7 | 0.0594 (16) | 0.0702 (19) | 0.0664 (19) | −0.0203 (13) | −0.0202 (13) | −0.0109 (14) |
C9 | 0.079 (2) | 0.081 (2) | 0.072 (2) | −0.0358 (16) | −0.0279 (16) | −0.0060 (16) |
O4_1 | 0.073 (11) | 0.091 (9) | 0.065 (7) | −0.011 (6) | −0.029 (6) | −0.029 (6) |
C8_1 | 0.078 (7) | 0.060 (6) | 0.066 (5) | −0.025 (5) | −0.029 (5) | −0.002 (4) |
C10_1 | 0.093 (11) | 0.047 (8) | 0.057 (6) | −0.028 (6) | −0.032 (7) | −0.012 (4) |
C11_1 | 0.088 (10) | 0.068 (9) | 0.060 (7) | −0.012 (6) | −0.032 (6) | −0.012 (5) |
C12_1 | 0.100 (10) | 0.090 (9) | 0.062 (8) | −0.035 (8) | −0.043 (8) | −0.017 (6) |
C13_1 | 0.040 (7) | 0.090 (6) | 0.041 (5) | −0.050 (5) | −0.004 (4) | 0.001 (4) |
C14_1 | 0.096 (14) | 0.094 (8) | 0.066 (7) | −0.026 (8) | −0.039 (7) | −0.016 (5) |
C15_1 | 0.094 (12) | 0.080 (9) | 0.068 (7) | −0.002 (7) | −0.044 (8) | −0.014 (6) |
O4_2 | 0.086 (9) | 0.086 (4) | 0.061 (3) | −0.022 (4) | −0.027 (3) | −0.003 (3) |
C8_2 | 0.067 (3) | 0.078 (4) | 0.074 (3) | −0.024 (3) | −0.026 (2) | −0.011 (2) |
C10_2 | 0.076 (5) | 0.071 (6) | 0.073 (4) | −0.019 (3) | −0.028 (3) | −0.009 (3) |
C11_2 | 0.089 (6) | 0.074 (7) | 0.075 (5) | −0.015 (4) | −0.037 (5) | −0.012 (4) |
C12_2 | 0.090 (4) | 0.096 (6) | 0.074 (5) | −0.020 (5) | −0.037 (4) | −0.020 (4) |
C13_2 | 0.047 (4) | 0.083 (4) | 0.062 (4) | −0.039 (3) | −0.009 (3) | −0.008 (3) |
C14_2 | 0.080 (6) | 0.091 (4) | 0.072 (4) | −0.024 (4) | −0.030 (3) | −0.015 (3) |
C15_2 | 0.078 (5) | 0.085 (5) | 0.075 (4) | −0.013 (3) | −0.030 (3) | −0.014 (3) |
C16_2 | 0.0712 (18) | 0.0588 (17) | 0.0642 (19) | −0.0208 (14) | −0.0236 (14) | −0.0042 (14) |
C17_2 | 0.0573 (15) | 0.0597 (17) | 0.0670 (19) | −0.0153 (13) | −0.0208 (13) | −0.0053 (13) |
C18_2 | 0.0748 (19) | 0.077 (2) | 0.067 (2) | −0.0291 (16) | −0.0208 (15) | −0.0048 (15) |
C19_2 | 0.076 (2) | 0.096 (2) | 0.074 (2) | −0.0429 (18) | −0.0173 (16) | −0.0016 (18) |
C20_2 | 0.0616 (17) | 0.073 (2) | 0.084 (2) | −0.0257 (14) | −0.0270 (15) | −0.0075 (16) |
C21_2 | 0.0640 (17) | 0.073 (2) | 0.075 (2) | −0.0218 (15) | −0.0238 (15) | −0.0100 (16) |
C22_2 | 0.0654 (17) | 0.0676 (18) | 0.0684 (19) | −0.0223 (14) | −0.0228 (14) | −0.0071 (14) |
O1_3 | 0.096 (7) | 0.060 (8) | 0.086 (6) | −0.019 (4) | 0.001 (5) | 0.009 (4) |
C1_3 | 0.100 (8) | 0.083 (8) | 0.091 (9) | −0.023 (6) | −0.006 (5) | −0.012 (6) |
C2_3 | 0.100 (8) | 0.080 (7) | 0.189 (14) | 0.002 (6) | 0.017 (7) | −0.022 (8) |
O1_4 | 0.134 (8) | 0.069 (8) | 0.102 (5) | −0.032 (5) | −0.019 (5) | −0.009 (5) |
C1_4 | 0.179 (15) | 0.154 (18) | 0.132 (10) | −0.079 (13) | −0.014 (7) | 0.018 (10) |
C2_4 | 0.174 (11) | 0.36 (2) | 0.077 (6) | −0.065 (12) | −0.031 (6) | 0.000 (9) |
O1—C7 | 1.370 (4) | C15_1—H15_1 | 0.9300 |
O1—C8_1 | 1.410 (9) | O4_2—H4_2 | 0.8200 |
O1—C8_2 | 1.433 (5) | O4_2—C13_2 | 1.397 (10) |
O2—H2 | 0.8200 | C8_2—H8_2 | 0.9800 |
O2—C5 | 1.359 (3) | C8_2—C10_2 | 1.506 (8) |
O3—H3 | 0.8200 | C10_2—C11_2 | 1.398 (10) |
O3—C3 | 1.363 (3) | C10_2—C15_2 | 1.356 (9) |
O5—C16_2 | 1.215 (3) | C11_2—H11_2 | 0.9300 |
O6—H6 | 0.8200 | C11_2—C12_2 | 1.383 (9) |
O6—C20_2 | 1.366 (3) | C12_2—H12_2 | 0.9300 |
N1—N2 | 1.380 (3) | C12_2—C13_2 | 1.393 (10) |
N1—C1 | 1.294 (4) | C13_2—C14_2 | 1.375 (9) |
N2—H2A | 0.8600 | C14_2—H14_2 | 0.9300 |
N2—C16_2 | 1.354 (4) | C14_2—C15_2 | 1.365 (9) |
C1—C2 | 1.471 (3) | C15_2—H15_2 | 0.9300 |
C1—C9 | 1.471 (4) | C16_2—C17_2 | 1.502 (4) |
C2—C3 | 1.403 (4) | C17_2—C18_2 | 1.378 (4) |
C2—C7 | 1.388 (4) | C17_2—C22_2 | 1.382 (4) |
C3—C4 | 1.385 (4) | C18_2—H18_2 | 0.9300 |
C4—H4 | 0.9300 | C18_2—C19_2 | 1.386 (4) |
C4—C5 | 1.377 (4) | C19_2—H19_2 | 0.9300 |
C5—C6 | 1.378 (4) | C19_2—C20_2 | 1.387 (5) |
C6—H6A | 0.9300 | C20_2—C21_2 | 1.355 (5) |
C6—C7 | 1.383 (4) | C21_2—H21_2 | 0.9300 |
C9—H9AA | 0.9700 | C21_2—C22_2 | 1.382 (4) |
C9—H9AB | 0.9700 | C22_2—H22_2 | 0.9300 |
C9—H9BC | 0.9700 | O1_3—H1_3 | 0.8200 |
C9—H9BD | 0.9700 | O1_3—C1_3 | 1.431 (11) |
C9—C8_1 | 1.494 (11) | C1_3—H1A_3 | 0.9700 |
C9—C8_2 | 1.469 (7) | C1_3—H1B_3 | 0.9700 |
O4_1—H4_1 | 0.8200 | C1_3—C2_3 | 1.541 (12) |
O4_1—C13_1 | 1.405 (15) | C2_3—H2A_3 | 0.9601 |
C8_1—H8_1 | 0.9800 | C2_3—H2B_3 | 0.9599 |
C8_1—C10_1 | 1.515 (11) | C2_3—H2C_3 | 0.9600 |
C10_1—C11_1 | 1.424 (14) | O1_4—H1_4 | 0.8200 |
C10_1—C15_1 | 1.375 (14) | O1_4—C1_4 | 1.448 (12) |
C11_1—H11_1 | 0.9300 | C1_4—H1A_4 | 0.9700 |
C11_1—C12_1 | 1.399 (13) | C1_4—H1B_4 | 0.9700 |
C12_1—H12_1 | 0.9300 | C1_4—C2_4 | 1.542 (14) |
C12_1—C13_1 | 1.401 (14) | C2_4—H2A_4 | 0.9600 |
C13_1—C14_1 | 1.379 (14) | C2_4—H2B_4 | 0.9601 |
C14_1—H14_1 | 0.9300 | C2_4—H2C_4 | 0.9600 |
C14_1—C15_1 | 1.341 (14) | ||
C7—O1—C8_1 | 115.5 (4) | O1—C8_2—C10_2 | 107.3 (4) |
C7—O1—C8_2 | 115.1 (3) | C9—C8_2—H8_2 | 107.0 |
C5—O2—H2 | 109.5 | C9—C8_2—C10_2 | 114.6 (5) |
C3—O3—H3 | 109.5 | C10_2—C8_2—H8_2 | 107.0 |
C20_2—O6—H6 | 109.5 | C11_2—C10_2—C8_2 | 117.9 (8) |
C1—N1—N2 | 119.6 (3) | C15_2—C10_2—C8_2 | 124.3 (8) |
N1—N2—H2A | 121.7 | C15_2—C10_2—C11_2 | 117.8 (6) |
C16_2—N2—N1 | 116.7 (3) | C10_2—C11_2—H11_2 | 118.9 |
C16_2—N2—H2A | 121.7 | C12_2—C11_2—C10_2 | 122.3 (7) |
N1—C1—C2 | 116.6 (3) | C12_2—C11_2—H11_2 | 118.9 |
N1—C1—C9 | 127.1 (3) | C11_2—C12_2—H12_2 | 121.2 |
C9—C1—C2 | 116.3 (3) | C11_2—C12_2—C13_2 | 117.6 (9) |
C3—C2—C1 | 122.7 (3) | C13_2—C12_2—H12_2 | 121.2 |
C7—C2—C1 | 119.9 (3) | C12_2—C13_2—O4_2 | 116.0 (9) |
C7—C2—C3 | 117.4 (3) | C14_2—C13_2—O4_2 | 122.3 (9) |
O3—C3—C2 | 121.4 (2) | C14_2—C13_2—C12_2 | 118.9 (8) |
O3—C3—C4 | 117.4 (3) | C13_2—C14_2—H14_2 | 119.3 |
C4—C3—C2 | 121.2 (3) | C15_2—C14_2—C13_2 | 121.5 (8) |
C3—C4—H4 | 120.4 | C15_2—C14_2—H14_2 | 119.3 |
C5—C4—C3 | 119.1 (3) | C10_2—C15_2—C14_2 | 121.0 (8) |
C5—C4—H4 | 120.4 | C10_2—C15_2—H15_2 | 119.5 |
O2—C5—C4 | 117.7 (3) | C14_2—C15_2—H15_2 | 119.5 |
O2—C5—C6 | 120.7 (3) | O5—C16_2—N2 | 121.7 (3) |
C4—C5—C6 | 121.5 (3) | O5—C16_2—C17_2 | 121.4 (3) |
C5—C6—H6A | 120.7 | N2—C16_2—C17_2 | 116.9 (3) |
C5—C6—C7 | 118.5 (3) | C18_2—C17_2—C16_2 | 117.1 (3) |
C7—C6—H6A | 120.7 | C18_2—C17_2—C22_2 | 118.7 (3) |
O1—C7—C2 | 121.9 (2) | C22_2—C17_2—C16_2 | 124.2 (3) |
O1—C7—C6 | 115.9 (3) | C17_2—C18_2—H18_2 | 119.6 |
C6—C7—C2 | 122.2 (3) | C17_2—C18_2—C19_2 | 120.9 (3) |
C1—C9—H9AA | 108.8 | C19_2—C18_2—H18_2 | 119.6 |
C1—C9—H9AB | 108.8 | C18_2—C19_2—H19_2 | 120.4 |
C1—C9—H9BC | 109.0 | C18_2—C19_2—C20_2 | 119.2 (3) |
C1—C9—H9BD | 109.0 | C20_2—C19_2—H19_2 | 120.4 |
C1—C9—C8_1 | 113.6 (4) | O6—C20_2—C19_2 | 116.6 (3) |
H9AA—C9—H9AB | 107.7 | C21_2—C20_2—O6 | 123.2 (3) |
H9BC—C9—H9BD | 107.8 | C21_2—C20_2—C19_2 | 120.2 (3) |
C8_1—C9—H9AA | 108.8 | C20_2—C21_2—H21_2 | 119.8 |
C8_1—C9—H9AB | 108.8 | C20_2—C21_2—C22_2 | 120.4 (3) |
C8_2—C9—C1 | 113.0 (3) | C22_2—C21_2—H21_2 | 119.8 |
C8_2—C9—H9BC | 109.0 | C17_2—C22_2—H22_2 | 119.7 |
C8_2—C9—H9BD | 109.0 | C21_2—C22_2—C17_2 | 120.5 (3) |
C13_1—O4_1—H4_1 | 109.4 | C21_2—C22_2—H22_2 | 119.7 |
O1—C8_1—C9 | 113.3 (8) | C1_3—O1_3—H1_3 | 109.5 |
O1—C8_1—H8_1 | 107.8 | O1_3—C1_3—H1A_3 | 109.3 |
O1—C8_1—C10_1 | 107.5 (7) | O1_3—C1_3—H1B_3 | 109.3 |
C9—C8_1—H8_1 | 107.8 | O1_3—C1_3—C2_3 | 111.6 (12) |
C9—C8_1—C10_1 | 112.3 (8) | H1A_3—C1_3—H1B_3 | 108.0 |
C10_1—C8_1—H8_1 | 107.8 | C2_3—C1_3—H1A_3 | 109.3 |
C11_1—C10_1—C8_1 | 115.7 (13) | C2_3—C1_3—H1B_3 | 109.3 |
C15_1—C10_1—C8_1 | 127.0 (13) | C1_3—C2_3—H2A_3 | 108.3 |
C15_1—C10_1—C11_1 | 117.3 (10) | C1_3—C2_3—H2B_3 | 114.2 |
C10_1—C11_1—H11_1 | 120.3 | C1_3—C2_3—H2C_3 | 105.8 |
C12_1—C11_1—C10_1 | 119.5 (12) | H2A_3—C2_3—H2B_3 | 109.5 |
C12_1—C11_1—H11_1 | 120.3 | H2A_3—C2_3—H2C_3 | 109.5 |
C11_1—C12_1—H12_1 | 120.8 | H2B_3—C2_3—H2C_3 | 109.5 |
C11_1—C12_1—C13_1 | 118.4 (13) | C1_4—O1_4—H1_4 | 109.5 |
C13_1—C12_1—H12_1 | 120.8 | O1_4—C1_4—H1A_4 | 109.4 |
C12_1—C13_1—O4_1 | 113.3 (16) | O1_4—C1_4—H1B_4 | 109.4 |
C14_1—C13_1—O4_1 | 119.9 (16) | O1_4—C1_4—C2_4 | 111.3 (13) |
C14_1—C13_1—C12_1 | 119.2 (13) | H1A_4—C1_4—H1B_4 | 108.0 |
C13_1—C14_1—H14_1 | 120.0 | C2_4—C1_4—H1A_4 | 109.4 |
C15_1—C14_1—C13_1 | 119.9 (15) | C2_4—C1_4—H1B_4 | 109.4 |
C15_1—C14_1—H14_1 | 120.0 | C1_4—C2_4—H2A_4 | 110.4 |
C10_1—C15_1—H15_1 | 118.4 | C1_4—C2_4—H2B_4 | 111.2 |
C14_1—C15_1—C10_1 | 123.1 (13) | C1_4—C2_4—H2C_4 | 106.7 |
C14_1—C15_1—H15_1 | 118.4 | H2A_4—C2_4—H2B_4 | 109.5 |
C13_2—O4_2—H4_2 | 109.7 | H2A_4—C2_4—H2C_4 | 109.5 |
O1—C8_2—C9 | 113.5 (5) | H2B_4—C2_4—H2C_4 | 109.5 |
O1—C8_2—H8_2 | 107.0 | ||
O1—C8_1—C10_1—C11_1 | −130.6 (15) | C7—C2—C3—O3 | −179.2 (3) |
O1—C8_1—C10_1—C15_1 | 50.2 (19) | C7—C2—C3—C4 | 1.4 (5) |
O1—C8_2—C10_2—C11_2 | −72.0 (8) | C9—C1—C2—C3 | 177.4 (3) |
O1—C8_2—C10_2—C15_2 | 110.1 (9) | C9—C1—C2—C7 | −2.1 (4) |
O2—C5—C6—C7 | −179.6 (3) | C9—C8_1—C10_1—C11_1 | 104.1 (16) |
O3—C3—C4—C5 | 178.0 (3) | C9—C8_1—C10_1—C15_1 | −75.1 (17) |
O5—C16_2—C17_2—C18_2 | 3.7 (5) | C9—C8_2—C10_2—C11_2 | 55.1 (9) |
O5—C16_2—C17_2—C22_2 | −176.2 (3) | C9—C8_2—C10_2—C15_2 | −122.8 (8) |
O6—C20_2—C21_2—C22_2 | −179.5 (3) | O4_1—C13_1—C14_1—C15_1 | −160 (3) |
N1—N2—C16_2—O5 | 1.6 (5) | C8_1—O1—C7—C2 | 25.8 (7) |
N1—N2—C16_2—C17_2 | −178.9 (2) | C8_1—O1—C7—C6 | −153.2 (7) |
N1—C1—C2—C3 | −1.8 (5) | C8_1—C10_1—C11_1—C12_1 | −178.8 (19) |
N1—C1—C2—C7 | 178.7 (3) | C8_1—C10_1—C15_1—C14_1 | −173.7 (18) |
N1—C1—C9—C8_1 | 157.7 (6) | C10_1—C11_1—C12_1—C13_1 | −13 (4) |
N1—C1—C9—C8_2 | −154.8 (4) | C11_1—C10_1—C15_1—C14_1 | 7 (3) |
N2—N1—C1—C2 | 178.4 (2) | C11_1—C12_1—C13_1—O4_1 | 169 (3) |
N2—N1—C1—C9 | −0.7 (5) | C11_1—C12_1—C13_1—C14_1 | 19 (4) |
N2—C16_2—C17_2—C18_2 | −175.8 (3) | C12_1—C13_1—C14_1—C15_1 | −12 (3) |
N2—C16_2—C17_2—C22_2 | 4.3 (5) | C13_1—C14_1—C15_1—C10_1 | −1 (3) |
C1—N1—N2—C16_2 | 174.2 (3) | C15_1—C10_1—C11_1—C12_1 | 0 (3) |
C1—C2—C3—O3 | 1.2 (5) | O4_2—C13_2—C14_2—C15_2 | 169.8 (14) |
C1—C2—C3—C4 | −178.2 (3) | C8_2—O1—C7—C2 | −24.7 (5) |
C1—C2—C7—O1 | 0.9 (5) | C8_2—O1—C7—C6 | 156.3 (4) |
C1—C2—C7—C6 | 179.8 (3) | C8_2—C10_2—C11_2—C12_2 | 179.6 (10) |
C1—C9—C8_1—O1 | 47.3 (10) | C8_2—C10_2—C15_2—C14_2 | 177.1 (9) |
C1—C9—C8_1—C10_1 | 169.4 (8) | C10_2—C11_2—C12_2—C13_2 | 9.0 (19) |
C1—C9—C8_2—O1 | −49.8 (6) | C11_2—C10_2—C15_2—C14_2 | −0.8 (14) |
C1—C9—C8_2—C10_2 | −173.6 (5) | C11_2—C12_2—C13_2—O4_2 | −173.6 (14) |
C2—C1—C9—C8_1 | −21.4 (7) | C11_2—C12_2—C13_2—C14_2 | −12.4 (19) |
C2—C1—C9—C8_2 | 26.1 (5) | C12_2—C13_2—C14_2—C15_2 | 9.7 (18) |
C2—C3—C4—C5 | −2.6 (5) | C13_2—C14_2—C15_2—C10_2 | −3.0 (17) |
C3—C2—C7—O1 | −178.7 (3) | C15_2—C10_2—C11_2—C12_2 | −2.4 (15) |
C3—C2—C7—C6 | 0.2 (5) | C16_2—C17_2—C18_2—C19_2 | 179.2 (3) |
C3—C4—C5—O2 | −178.8 (3) | C16_2—C17_2—C22_2—C21_2 | −178.7 (3) |
C3—C4—C5—C6 | 2.3 (5) | C17_2—C18_2—C19_2—C20_2 | −0.1 (6) |
C4—C5—C6—C7 | −0.7 (5) | C18_2—C17_2—C22_2—C21_2 | 1.5 (5) |
C5—C6—C7—O1 | 178.4 (3) | C18_2—C19_2—C20_2—O6 | −179.9 (3) |
C5—C6—C7—C2 | −0.5 (5) | C18_2—C19_2—C20_2—C21_2 | 0.6 (6) |
C7—O1—C8_1—C9 | −49.7 (10) | C19_2—C20_2—C21_2—C22_2 | 0.0 (5) |
C7—O1—C8_1—C10_1 | −174.4 (8) | C20_2—C21_2—C22_2—C17_2 | −1.0 (5) |
C7—O1—C8_2—C9 | 49.4 (6) | C22_2—C17_2—C18_2—C19_2 | −0.9 (5) |
C7—O1—C8_2—C10_2 | 177.2 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···N1 | 0.82 | 1.82 | 2.542 (3) | 147 |
O6—H6···O2i | 0.82 | 2.12 | 2.739 (4) | 132 |
O4_1—H4_1···O3ii | 0.82 | 1.87 | 2.52 (3) | 136 |
O4_2—H4_2···O3ii | 0.82 | 1.96 | 2.728 (15) | 156 |
O1_3—H1_3···O5iii | 0.82 | 1.92 | 2.62 (2) | 144 |
O1_4—H1_4···O5iii | 0.82 | 2.28 | 2.877 (17) | 130 |
Symmetry codes: (i) x+1, y+1, z; (ii) x, y, z+1; (iii) −x, −y+2, −z+1. |
C28H24N2O4 | Z = 2 |
Mr = 452.49 | F(000) = 476 |
Triclinic, P1 | Dx = 1.335 Mg m−3 |
a = 5.0681 (6) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 13.4993 (15) Å | Cell parameters from 3831 reflections |
c = 17.1144 (18) Å | θ = 3.7–73.1° |
α = 74.392 (9)° | µ = 0.73 mm−1 |
β = 86.34 (1)° | T = 293 K |
γ = 88.416 (10)° | Needle, clear yellow |
V = 1125.4 (2) Å3 | 0.17 × 0.04 × 0.03 mm |
ROD, Synergy Custom system, HyPix-Arc 150 diffractometer | 4404 independent reflections |
Radiation source: Rotating-anode X-ray tube, Rigaku (Cu) X-ray Source | 1823 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.051 |
Detector resolution: 10.0000 pixels mm-1 | θmax = 76.5°, θmin = 3.4° |
ω scans | h = −5→6 |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2022) | k = −16→16 |
Tmin = 0.889, Tmax = 1.000 | l = −21→20 |
11899 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.077 | w = 1/[σ2(Fo2) + (0.1489P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.285 | (Δ/σ)max < 0.001 |
S = 0.99 | Δρmax = 0.31 e Å−3 |
4404 reflections | Δρmin = −0.24 e Å−3 |
309 parameters | Extinction correction: SHELXL-2018/3 (Sheldrick 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
6 restraints | Extinction coefficient: 0.0075 (16) |
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 | ||
O1 | 0.1662 (5) | 0.3408 (2) | 0.51160 (17) | 0.0808 (9) | |
O2 | 0.3870 (6) | 0.5290 (2) | 0.18760 (17) | 0.0873 (10) | |
O3 | 1.2146 (6) | 0.0164 (2) | 0.41472 (17) | 0.0801 (9) | |
O4 | 0.9806 (6) | 0.1395 (2) | 0.24739 (15) | 0.0734 (9) | |
N1 | 0.7481 (6) | 0.2143 (2) | 0.38761 (19) | 0.0665 (9) | |
N2 | 0.8829 (6) | 0.1260 (3) | 0.42458 (19) | 0.0676 (9) | |
H2 | 0.836029 | 0.091524 | 0.473277 | 0.081* | |
C1 | 0.5738 (8) | 0.2504 (3) | 0.4307 (2) | 0.0640 (10) | |
C9 | 0.4980 (9) | 0.2062 (3) | 0.5185 (2) | 0.0783 (13) | |
H9A | 0.388021 | 0.146606 | 0.524494 | 0.094* | |
H9B | 0.656544 | 0.183096 | 0.547337 | 0.094* | |
C8 | 0.3562 (11) | 0.2788 (4) | 0.5551 (3) | 0.1022 (18) | |
H8 | 0.493593 | 0.327843 | 0.556598 | 0.123* | |
C2 | 0.4336 (7) | 0.3430 (3) | 0.3891 (2) | 0.0628 (10) | |
C7 | 0.2328 (8) | 0.3834 (3) | 0.4300 (2) | 0.0690 (11) | |
C6 | 0.0890 (8) | 0.4682 (3) | 0.3908 (3) | 0.0789 (13) | |
H6 | −0.046360 | 0.494164 | 0.419216 | 0.095* | |
C5 | 0.1448 (9) | 0.5139 (4) | 0.3106 (3) | 0.0803 (13) | |
H5 | 0.046166 | 0.570841 | 0.284228 | 0.096* | |
C4 | 0.3478 (8) | 0.4764 (3) | 0.2679 (3) | 0.0709 (12) | |
C3 | 0.4898 (8) | 0.3925 (3) | 0.3065 (2) | 0.0669 (11) | |
H3 | 0.626100 | 0.367444 | 0.277822 | 0.080* | |
C10 | 0.2606 (8) | 0.2418 (3) | 0.6417 (3) | 0.0769 (13) | |
C11 | 0.0709 (9) | 0.1683 (4) | 0.6671 (3) | 0.0991 (16) | |
H11 | 0.002437 | 0.138749 | 0.629577 | 0.119* | |
C12 | −0.0191 (11) | 0.1377 (5) | 0.7459 (4) | 0.123 (2) | |
H12 | −0.148713 | 0.087663 | 0.761742 | 0.148* | |
C13 | 0.0766 (14) | 0.1789 (5) | 0.8018 (4) | 0.126 (3) | |
H13 | 0.010054 | 0.158714 | 0.855512 | 0.151* | |
C14 | 0.2700 (14) | 0.2496 (5) | 0.7791 (4) | 0.122 (2) | |
H14 | 0.340262 | 0.276882 | 0.817627 | 0.146* | |
C15 | 0.3630 (10) | 0.2812 (4) | 0.6993 (3) | 0.0975 (16) | |
H15 | 0.496450 | 0.329700 | 0.684040 | 0.117* | |
C16 | 1.0878 (8) | 0.0944 (3) | 0.3838 (2) | 0.0635 (10) | |
C17 | 1.1610 (8) | 0.1602 (3) | 0.2998 (2) | 0.0686 (11) | |
H17A | 1.152062 | 0.232409 | 0.298819 | 0.082* | |
H17B | 1.339762 | 0.144127 | 0.282862 | 0.082* | |
C18 | 0.9661 (8) | 0.2057 (3) | 0.1711 (2) | 0.0664 (11) | |
C19 | 1.1124 (9) | 0.2940 (3) | 0.1450 (2) | 0.0783 (13) | |
H19 | 1.228505 | 0.311241 | 0.179050 | 0.094* | |
C20 | 1.0843 (10) | 0.3574 (4) | 0.0665 (3) | 0.0871 (15) | |
H20 | 1.181766 | 0.417527 | 0.049067 | 0.105* | |
C21 | 0.9201 (9) | 0.3338 (4) | 0.0157 (3) | 0.0835 (14) | |
H21 | 0.906878 | 0.377231 | −0.036360 | 0.100* | |
C22 | 0.7663 (8) | 0.2428 (4) | 0.0409 (3) | 0.0745 (12) | |
C23 | 0.5937 (10) | 0.2149 (4) | −0.0094 (3) | 0.0892 (14) | |
H23 | 0.577497 | 0.256913 | −0.061720 | 0.107* | |
C24 | 0.4485 (11) | 0.1279 (5) | 0.0160 (4) | 0.1064 (17) | |
H24 | 0.332690 | 0.110928 | −0.018255 | 0.128* | |
C25 | 0.4757 (11) | 0.0636 (4) | 0.0951 (3) | 0.0992 (17) | |
H25 | 0.378521 | 0.003345 | 0.112441 | 0.119* | |
C26 | 0.6395 (8) | 0.0876 (3) | 0.1459 (3) | 0.0782 (13) | |
H26 | 0.653446 | 0.044377 | 0.197940 | 0.094* | |
C27 | 0.7907 (8) | 0.1786 (3) | 0.1205 (2) | 0.0665 (11) | |
C28 | 0.6094 (9) | 0.4996 (4) | 0.1449 (3) | 0.0982 (17) | |
H28A | 0.624427 | 0.544273 | 0.090701 | 0.147* | |
H28B | 0.589265 | 0.429952 | 0.142465 | 0.147* | |
H28C | 0.765986 | 0.504397 | 0.172318 | 0.147* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0821 (18) | 0.091 (2) | 0.0612 (18) | 0.0282 (16) | −0.0048 (15) | −0.0090 (15) |
O2 | 0.092 (2) | 0.084 (2) | 0.0690 (19) | 0.0149 (17) | −0.0009 (17) | 0.0044 (16) |
O3 | 0.0884 (19) | 0.080 (2) | 0.0646 (18) | 0.0234 (16) | −0.0024 (15) | −0.0105 (15) |
O4 | 0.0956 (19) | 0.0717 (18) | 0.0488 (15) | −0.0066 (15) | −0.0098 (14) | −0.0071 (13) |
N1 | 0.0739 (19) | 0.060 (2) | 0.062 (2) | 0.0149 (16) | −0.0072 (17) | −0.0109 (16) |
N2 | 0.075 (2) | 0.071 (2) | 0.0536 (18) | 0.0181 (17) | −0.0033 (16) | −0.0133 (16) |
C1 | 0.068 (2) | 0.062 (2) | 0.061 (2) | 0.0055 (19) | −0.006 (2) | −0.014 (2) |
C9 | 0.084 (3) | 0.086 (3) | 0.061 (3) | 0.018 (2) | −0.002 (2) | −0.016 (2) |
C8 | 0.122 (4) | 0.102 (4) | 0.068 (3) | 0.043 (3) | 0.007 (3) | −0.004 (3) |
C2 | 0.061 (2) | 0.062 (2) | 0.065 (2) | 0.0057 (19) | −0.0061 (19) | −0.016 (2) |
C7 | 0.070 (2) | 0.075 (3) | 0.059 (2) | 0.005 (2) | −0.005 (2) | −0.014 (2) |
C6 | 0.079 (3) | 0.081 (3) | 0.073 (3) | 0.026 (2) | −0.006 (2) | −0.016 (2) |
C5 | 0.082 (3) | 0.075 (3) | 0.076 (3) | 0.018 (2) | −0.002 (2) | −0.010 (2) |
C4 | 0.075 (2) | 0.069 (3) | 0.063 (3) | 0.002 (2) | −0.008 (2) | −0.007 (2) |
C3 | 0.070 (2) | 0.067 (3) | 0.060 (2) | 0.005 (2) | −0.003 (2) | −0.011 (2) |
C10 | 0.081 (3) | 0.078 (3) | 0.066 (3) | 0.017 (2) | 0.004 (2) | −0.014 (2) |
C11 | 0.098 (3) | 0.116 (4) | 0.085 (4) | −0.008 (3) | −0.010 (3) | −0.028 (3) |
C12 | 0.108 (4) | 0.142 (6) | 0.101 (5) | −0.007 (4) | 0.019 (4) | −0.005 (4) |
C13 | 0.155 (6) | 0.137 (6) | 0.070 (4) | 0.055 (5) | 0.005 (4) | −0.010 (4) |
C14 | 0.165 (6) | 0.125 (5) | 0.090 (5) | 0.039 (5) | −0.047 (4) | −0.050 (4) |
C15 | 0.104 (4) | 0.089 (4) | 0.101 (4) | 0.001 (3) | −0.020 (3) | −0.025 (3) |
C16 | 0.068 (2) | 0.067 (3) | 0.055 (2) | 0.009 (2) | −0.0058 (19) | −0.016 (2) |
C17 | 0.078 (2) | 0.077 (3) | 0.049 (2) | 0.000 (2) | −0.006 (2) | −0.013 (2) |
C18 | 0.079 (2) | 0.066 (3) | 0.048 (2) | 0.006 (2) | 0.000 (2) | −0.0062 (19) |
C19 | 0.094 (3) | 0.073 (3) | 0.060 (3) | −0.007 (2) | −0.006 (2) | −0.004 (2) |
C20 | 0.102 (3) | 0.079 (3) | 0.069 (3) | −0.007 (3) | 0.000 (3) | 0.000 (2) |
C21 | 0.095 (3) | 0.085 (3) | 0.062 (3) | 0.003 (3) | −0.002 (3) | −0.005 (2) |
C22 | 0.080 (3) | 0.081 (3) | 0.061 (3) | 0.018 (2) | −0.009 (2) | −0.018 (2) |
C23 | 0.099 (3) | 0.104 (4) | 0.066 (3) | 0.019 (3) | −0.025 (3) | −0.022 (3) |
C24 | 0.110 (4) | 0.121 (5) | 0.098 (4) | 0.007 (4) | −0.032 (3) | −0.039 (4) |
C25 | 0.105 (4) | 0.103 (4) | 0.093 (4) | −0.016 (3) | −0.019 (3) | −0.027 (3) |
C26 | 0.086 (3) | 0.079 (3) | 0.069 (3) | 0.000 (2) | −0.007 (2) | −0.018 (2) |
C27 | 0.072 (2) | 0.073 (3) | 0.055 (2) | 0.008 (2) | −0.005 (2) | −0.017 (2) |
C28 | 0.096 (3) | 0.102 (4) | 0.082 (3) | 0.002 (3) | 0.010 (3) | −0.004 (3) |
O1—C8 | 1.376 (5) | C12—H12 | 0.9300 |
O1—C7 | 1.383 (4) | C12—C13 | 1.349 (7) |
O2—C4 | 1.371 (5) | C13—H13 | 0.9300 |
O2—C28 | 1.411 (5) | C13—C14 | 1.351 (6) |
O3—C16 | 1.228 (5) | C14—H14 | 0.9300 |
O4—C17 | 1.404 (5) | C14—C15 | 1.374 (6) |
O4—C18 | 1.374 (4) | C15—H15 | 0.9300 |
N1—N2 | 1.376 (4) | C16—C17 | 1.503 (5) |
N1—C1 | 1.284 (5) | C17—H17A | 0.9700 |
N2—H2 | 0.8600 | C17—H17B | 0.9700 |
N2—C16 | 1.338 (5) | C18—C19 | 1.374 (5) |
C1—C9 | 1.488 (5) | C18—C27 | 1.401 (6) |
C1—C2 | 1.453 (5) | C19—H19 | 0.9300 |
C9—H9A | 0.9700 | C19—C20 | 1.399 (6) |
C9—H9B | 0.9700 | C20—H20 | 0.9300 |
C9—C8 | 1.451 (6) | C20—C21 | 1.345 (7) |
C8—H8 | 0.9800 | C21—H21 | 0.9300 |
C8—C10 | 1.485 (6) | C21—C22 | 1.425 (6) |
C2—C7 | 1.382 (5) | C22—C23 | 1.392 (6) |
C2—C3 | 1.406 (5) | C22—C27 | 1.414 (6) |
C7—C6 | 1.376 (6) | C23—H23 | 0.9300 |
C6—H6 | 0.9300 | C23—C24 | 1.357 (7) |
C6—C5 | 1.360 (5) | C24—H24 | 0.9300 |
C5—H5 | 0.9300 | C24—C25 | 1.410 (7) |
C5—C4 | 1.387 (6) | C25—H25 | 0.9300 |
C4—C3 | 1.361 (5) | C25—C26 | 1.345 (6) |
C3—H3 | 0.9300 | C26—H26 | 0.9300 |
C10—C11 | 1.366 (5) | C26—C27 | 1.416 (6) |
C10—C15 | 1.372 (6) | C28—H28A | 0.9600 |
C11—H11 | 0.9300 | C28—H28B | 0.9600 |
C11—C12 | 1.352 (6) | C28—H28C | 0.9600 |
C8—O1—C7 | 115.8 (3) | C13—C14—H14 | 120.0 |
C4—O2—C28 | 116.6 (4) | C13—C14—C15 | 120.1 (6) |
C18—O4—C17 | 118.8 (3) | C15—C14—H14 | 120.0 |
C1—N1—N2 | 118.2 (3) | C10—C15—C14 | 120.6 (5) |
N1—N2—H2 | 120.4 | C10—C15—H15 | 119.7 |
C16—N2—N1 | 119.1 (3) | C14—C15—H15 | 119.7 |
C16—N2—H2 | 120.4 | O3—C16—N2 | 121.2 (3) |
N1—C1—C9 | 126.7 (4) | O3—C16—C17 | 121.6 (3) |
N1—C1—C2 | 116.4 (3) | N2—C16—C17 | 117.2 (4) |
C2—C1—C9 | 116.8 (3) | O4—C17—C16 | 107.4 (3) |
C1—C9—H9A | 109.0 | O4—C17—H17A | 110.2 |
C1—C9—H9B | 109.0 | O4—C17—H17B | 110.2 |
H9A—C9—H9B | 107.8 | C16—C17—H17A | 110.2 |
C8—C9—C1 | 113.0 (4) | C16—C17—H17B | 110.2 |
C8—C9—H9A | 109.0 | H17A—C17—H17B | 108.5 |
C8—C9—H9B | 109.0 | O4—C18—C27 | 116.1 (3) |
O1—C8—C9 | 118.2 (5) | C19—C18—O4 | 122.8 (4) |
O1—C8—H8 | 102.8 | C19—C18—C27 | 121.1 (4) |
O1—C8—C10 | 109.7 (4) | C18—C19—H19 | 120.4 |
C9—C8—H8 | 102.8 | C18—C19—C20 | 119.1 (5) |
C9—C8—C10 | 117.8 (4) | C20—C19—H19 | 120.4 |
C10—C8—H8 | 102.8 | C19—C20—H20 | 119.1 |
C7—C2—C1 | 120.0 (4) | C21—C20—C19 | 121.8 (4) |
C7—C2—C3 | 117.8 (4) | C21—C20—H20 | 119.1 |
C3—C2—C1 | 122.1 (4) | C20—C21—H21 | 119.8 |
C2—C7—O1 | 121.9 (4) | C20—C21—C22 | 120.4 (4) |
C6—C7—O1 | 117.0 (4) | C22—C21—H21 | 119.8 |
C6—C7—C2 | 121.1 (4) | C23—C22—C21 | 122.6 (4) |
C7—C6—H6 | 120.0 | C23—C22—C27 | 119.0 (4) |
C5—C6—C7 | 120.0 (4) | C27—C22—C21 | 118.4 (4) |
C5—C6—H6 | 120.0 | C22—C23—H23 | 119.2 |
C6—C5—H5 | 119.7 | C24—C23—C22 | 121.7 (5) |
C6—C5—C4 | 120.5 (4) | C24—C23—H23 | 119.2 |
C4—C5—H5 | 119.7 | C23—C24—H24 | 120.4 |
O2—C4—C5 | 115.4 (4) | C23—C24—C25 | 119.1 (5) |
C3—C4—O2 | 125.1 (4) | C25—C24—H24 | 120.4 |
C3—C4—C5 | 119.6 (4) | C24—C25—H25 | 119.4 |
C2—C3—H3 | 119.5 | C26—C25—C24 | 121.3 (5) |
C4—C3—C2 | 121.0 (4) | C26—C25—H25 | 119.4 |
C4—C3—H3 | 119.5 | C25—C26—H26 | 119.9 |
C11—C10—C8 | 122.0 (5) | C25—C26—C27 | 120.3 (4) |
C11—C10—C15 | 117.8 (4) | C27—C26—H26 | 119.9 |
C15—C10—C8 | 120.2 (5) | C18—C27—C22 | 119.3 (4) |
C10—C11—H11 | 119.5 | C18—C27—C26 | 122.0 (4) |
C12—C11—C10 | 121.0 (5) | C22—C27—C26 | 118.7 (4) |
C12—C11—H11 | 119.5 | O2—C28—H28A | 109.5 |
C11—C12—H12 | 119.6 | O2—C28—H28B | 109.5 |
C13—C12—C11 | 120.9 (6) | O2—C28—H28C | 109.5 |
C13—C12—H12 | 119.6 | H28A—C28—H28B | 109.5 |
C12—C13—H13 | 120.2 | H28A—C28—H28C | 109.5 |
C12—C13—C14 | 119.5 (6) | H28B—C28—H28C | 109.5 |
C14—C13—H13 | 120.2 | ||
O1—C8—C10—C11 | 73.5 (6) | C7—C6—C5—C4 | −0.6 (7) |
O1—C8—C10—C15 | −106.7 (6) | C6—C5—C4—O2 | −179.6 (4) |
O1—C7—C6—C5 | 179.8 (4) | C6—C5—C4—C3 | 0.7 (7) |
O2—C4—C3—C2 | −179.5 (4) | C5—C4—C3—C2 | 0.1 (6) |
O3—C16—C17—O4 | 103.6 (5) | C3—C2—C7—O1 | −179.0 (4) |
O4—C18—C19—C20 | −179.6 (4) | C3—C2—C7—C6 | 1.2 (6) |
O4—C18—C27—C22 | −179.7 (4) | C10—C11—C12—C13 | −0.2 (10) |
O4—C18—C27—C26 | −0.7 (6) | C11—C10—C15—C14 | −2.1 (8) |
N1—N2—C16—O3 | 179.5 (4) | C11—C12—C13—C14 | −1.8 (11) |
N1—N2—C16—C17 | 1.4 (5) | C12—C13—C14—C15 | 1.7 (10) |
N1—C1—C9—C8 | 162.8 (5) | C13—C14—C15—C10 | 0.2 (9) |
N1—C1—C2—C7 | 176.4 (4) | C15—C10—C11—C12 | 2.1 (8) |
N1—C1—C2—C3 | −1.7 (6) | C17—O4—C18—C19 | −2.9 (6) |
N2—N1—C1—C9 | −0.2 (6) | C17—O4—C18—C27 | 177.3 (3) |
N2—N1—C1—C2 | −179.2 (3) | C18—O4—C17—C16 | 165.4 (3) |
N2—C16—C17—O4 | −78.3 (4) | C18—C19—C20—C21 | −0.7 (8) |
C1—N1—N2—C16 | −171.6 (4) | C19—C18—C27—C22 | 0.5 (6) |
C1—C9—C8—O1 | 42.0 (7) | C19—C18—C27—C26 | 179.5 (4) |
C1—C9—C8—C10 | 177.5 (4) | C19—C20—C21—C22 | 0.6 (8) |
C1—C2—C7—O1 | 2.8 (6) | C20—C21—C22—C23 | −180.0 (5) |
C1—C2—C7—C6 | −176.9 (4) | C20—C21—C22—C27 | 0.1 (7) |
C1—C2—C3—C4 | 177.0 (4) | C21—C22—C23—C24 | −179.8 (5) |
C9—C1—C2—C7 | −2.7 (6) | C21—C22—C27—C18 | −0.7 (6) |
C9—C1—C2—C3 | 179.2 (4) | C21—C22—C27—C26 | −179.7 (4) |
C9—C8—C10—C11 | −65.5 (7) | C22—C23—C24—C25 | −0.8 (8) |
C9—C8—C10—C15 | 114.3 (6) | C23—C22—C27—C18 | 179.4 (4) |
C8—O1—C7—C2 | 19.7 (6) | C23—C22—C27—C26 | 0.4 (6) |
C8—O1—C7—C6 | −160.6 (5) | C23—C24—C25—C26 | 1.0 (9) |
C8—C10—C11—C12 | −178.1 (5) | C24—C25—C26—C27 | −0.5 (8) |
C8—C10—C15—C14 | 178.1 (5) | C25—C26—C27—C18 | −179.2 (4) |
C2—C1—C9—C8 | −18.2 (6) | C25—C26—C27—C22 | −0.2 (7) |
C2—C7—C6—C5 | −0.4 (7) | C27—C18—C19—C20 | 0.2 (7) |
C7—O1—C8—C9 | −43.1 (6) | C27—C22—C23—C24 | 0.1 (7) |
C7—O1—C8—C10 | 178.1 (4) | C28—O2—C4—C5 | 173.4 (4) |
C7—C2—C3—C4 | −1.1 (6) | C28—O2—C4—C3 | −6.9 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O3i | 0.86 | 2.08 | 2.922 (4) | 167 |
Symmetry code: (i) −x+2, −y, −z+1. |
Acknowledgements
Research reported here was conducted on instrumentation funded by SIG S10 grants of the National Institutes of Health under award Nos. 1S10OD028589–01 and 1S10RR023439–01 to Dr Neela Yennawar.
Funding information
Funding for this research was provided by: Pennsylvania State University (grant No. CCRCDP 150000005862 to Dr Anna Sigmon).
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