organic compounds
2-Methyl-3′-(4-methylphenyl)-4′-(2-nitrophenyl)-4′H-spiro[chroman-3,5′-isoxazol]-4-one
aLaboratoire de Chimie Organique, Faculté des Sciences Dhar EL Mahraz, Université Sidi Mohamed Ben Abdellah, BP 1796, 30000, Fès, Morocco, and bLaboratoire de Chimie Appliquée des Matériaux, Centres des Sciences des Matériaux, Faculty of Sciences, Mohammed V University in Rabat, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
*Correspondence e-mail: asmae.mahfoud@yahoo.fr
The title compound, C25H20N2O5, crystallizes with two molecules (A and B) in the with similar conformations. The five-membered rings are both in envelope conformations with the spiro C atom as the flap. The six-membered heterocycles display half-chair conformations. The mean plane through the isoxazole ring is nearly perpendicular to those through the spiro-chroman system and the 4-nitrophenyl moieties, as indicated by the dihedral angles of 81.42 (9) and 87.58 (8)°, respectively, between them in molecule A. Equivalent data for molecule B are 75.58 (9) and 84.15 (8)°, respectively. The p-tolyl plane makes a dihedral angles of 24.10 (9) and 28.78 (8)° with the isoxazole ring in molecules A and B, respectively. In the crystal, molecules are linked by C—H⋯O and C—H⋯N hydrogen bonds and C—H⋯π interaction, forming a three-dimensional network.
Keywords: crystal structure; nitrophenyl; chroman-4-one; isoxazol; hydrogen bonds.
CCDC reference: 1853501
Structure description
Spiroisoxazolines have various biological properties such as herbicidal (De Amici et al., 1990)and plant-growth regulatory activities (Howe & Shelton, 1990) and have applications as antitumor agents (Smietana et al., 1999) and anti-HIV agents (Liu et al., 1997). In this work we have studied the regio- and of spiroisoxazoline 2-methyl-4′-(nitrophenyl)-3′-(p-tolyl)-4′H-spiro[chroman-3,5′-isoxazol]-4-one obtained by the 1,3-dipolar cycloaddition (Mahfoud et al., 2015, Boughaleb et al., 2011) of (E)-2-methyl-3-(4-nitrobenzylidene)chroman-4-one and 4-tolylbenzonitrile oxide. This concerted reaction affords a single regio-isomer which is the trans-spiroisoxazoline (Bakhouch et al., 2014). The structure of the product was confirmed by the present X-ray study.
The A and B) with almost the same conformation, as shown in Fig. 1. The most important difference between them lies in the orientation of the phenyl rings, as can be seen in the overlay plot (Fig. 2). The isoxazole ring belonging to each molecule is linked to a spiro-chroman system with additional 3′-p-tolyl and 4-nitrophenyl ring substituents. The five-membered rings (N1/O3/C9/C10/C18) and (N3/O8/C34/C35/C43) display envelope conformations on C9 and C43, as indicated by the total puckering amplitudes Q2 = 0.3093 (15) and 0.3143 (15) Å and spherical polar angles φ2 = 138.2 (3) and 138.4 (3)°, respectively. Moreover, the six-membered heterocycles adopt half-chair conformations with the following puckering parameters: Q = 0.4758 (17) Å, θ = 129.2 (2)°, φ2 = 97.0 (2)° for molecule A and Q = 0.4409 (17) Å, θ = 50.5 (2)°, φ2 = 270.8 (3)°, for B. The dihedral angles between the mean plane through the isoxazole rings and the p-tolyl planes are 24.10 (9) and 28.78 (8)°, in molecules A and B, respectively. The mean plane through the isoxazole ring is nearly perpendicular to those through the spiro-chroman system and the 4-nitrophenyl moieties, as indicated by the dihedral angles of 81.42 (9) and 87.58 (8)°, respectively, between them in molecule A [75.58 (9) and 84.15 (8)°, respectively in B].
of the title compound is formed by two molecules (In the crystal, the molecules are linked by C10—H10⋯O1, C35—H35⋯O6 and C16—H16⋯N3 hydrogen bonds, in addition to C23—H23⋯π(Cg1) and C30—H30⋯π(Cg2) interactions, forming a three-dimensional network as shown in Fig. 3 and Table 1.
Synthesis and crystallization
In a 100 ml flask, 2 mmol of (E)-2-methyl-3-(4-nitrobenzylidene) chroman-4-one and 2.4 mmol of p-tolylnitrioxide were dissolved in 20 ml of chloroform. The mixture was cooled to 273 K under magnetic stirring in an ice bath. Then, 15 ml of bleach (NaOCl) at 18° was added in small doses without exceeding 278 K. The mixture was left under magnetic stirring for 16 h at room temperature, then washed with water until the pH was neutral and dried on sodium sulfate. The solvent was removed under reduced pressure to leave an oily residue. The precipitated compound was then recrystallized from ethanol solution as colourless blocks.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
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Structural data
CCDC reference: 1853501
https://doi.org/10.1107/S2414314618009628/hb4244sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618009628/hb4244Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314618009628/hb4244Isup3.cml
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: Mercury (Macrae et al., 2008) and publCIF (Westrip, 2010).C25H20N2O5 | Z = 4 |
Mr = 428.43 | F(000) = 896 |
Triclinic, P1 | Dx = 1.323 Mg m−3 |
a = 11.5219 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 14.2321 (7) Å | Cell parameters from 10255 reflections |
c = 14.7033 (7) Å | θ = 2.1–27.9° |
α = 72.201 (2)° | µ = 0.09 mm−1 |
β = 73.469 (2)° | T = 296 K |
γ = 73.647 (2)° | Block, colourless |
V = 2150.18 (19) Å3 | 0.36 × 0.28 × 0.25 mm |
Bruker X8 APEX diffractometer | 10255 independent reflections |
Radiation source: fine-focus sealed tube | 7363 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
φ and ω scans | θmax = 27.9°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −15→15 |
Tmin = 0.639, Tmax = 0.747 | k = −18→18 |
86936 measured reflections | l = −19→19 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.122 | w = 1/[σ2(Fo2) + (0.0486P)2 + 0.6603P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.010 |
10255 reflections | Δρmax = 0.23 e Å−3 |
581 parameters | Δρmin = −0.26 e Å−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 | ||
C1 | 0.71087 (13) | 0.49608 (11) | 0.37433 (10) | 0.0365 (3) | |
C2 | 0.79239 (13) | 0.45907 (11) | 0.29001 (10) | 0.0388 (3) | |
C3 | 0.75481 (16) | 0.48309 (12) | 0.20169 (11) | 0.0495 (4) | |
H3 | 0.676591 | 0.522713 | 0.196050 | 0.059* | |
C4 | 0.83235 (19) | 0.44868 (15) | 0.12350 (13) | 0.0623 (5) | |
H4 | 0.806249 | 0.463973 | 0.065331 | 0.075* | |
C5 | 0.9494 (2) | 0.39122 (16) | 0.13101 (14) | 0.0678 (5) | |
H5 | 1.002242 | 0.369206 | 0.077203 | 0.081* | |
C6 | 0.98877 (17) | 0.36613 (15) | 0.21703 (13) | 0.0600 (5) | |
H6 | 1.067477 | 0.326919 | 0.221550 | 0.072* | |
C7 | 0.91024 (14) | 0.39975 (12) | 0.29698 (11) | 0.0428 (3) | |
C8 | 0.86434 (14) | 0.37965 (12) | 0.47069 (11) | 0.0421 (3) | |
H8 | 0.914902 | 0.373053 | 0.517865 | 0.051* | |
C9 | 0.77534 (12) | 0.48180 (11) | 0.45741 (10) | 0.0357 (3) | |
C10 | 0.68255 (12) | 0.51028 (10) | 0.54800 (10) | 0.0343 (3) | |
H10 | 0.602563 | 0.494634 | 0.554534 | 0.041* | |
C11 | 0.72823 (12) | 0.46262 (10) | 0.64259 (10) | 0.0346 (3) | |
C12 | 0.82793 (14) | 0.48833 (12) | 0.65780 (11) | 0.0443 (4) | |
H12 | 0.862619 | 0.540155 | 0.612152 | 0.053* | |
C13 | 0.87597 (15) | 0.43763 (14) | 0.74007 (12) | 0.0493 (4) | |
H13 | 0.942495 | 0.455001 | 0.750203 | 0.059* | |
C14 | 0.82365 (15) | 0.36116 (13) | 0.80655 (11) | 0.0460 (4) | |
C15 | 0.72337 (15) | 0.33473 (12) | 0.79497 (11) | 0.0466 (4) | |
H15 | 0.689002 | 0.283001 | 0.841108 | 0.056* | |
C16 | 0.67506 (14) | 0.38710 (11) | 0.71294 (11) | 0.0405 (3) | |
H16 | 0.606059 | 0.371505 | 0.704844 | 0.049* | |
C17 | 0.79860 (17) | 0.29277 (12) | 0.50363 (13) | 0.0533 (4) | |
H17A | 0.752555 | 0.298441 | 0.456400 | 0.080* | |
H17B | 0.742974 | 0.294719 | 0.565910 | 0.080* | |
H17C | 0.858576 | 0.230032 | 0.509483 | 0.080* | |
C18 | 0.67423 (14) | 0.62358 (11) | 0.51415 (10) | 0.0392 (3) | |
C19 | 0.56998 (15) | 0.69988 (11) | 0.54889 (11) | 0.0418 (3) | |
C20 | 0.48044 (16) | 0.67386 (13) | 0.63232 (12) | 0.0504 (4) | |
H20 | 0.488054 | 0.607106 | 0.668633 | 0.060* | |
C21 | 0.37977 (18) | 0.74655 (15) | 0.66194 (14) | 0.0599 (5) | |
H21 | 0.320723 | 0.727894 | 0.718208 | 0.072* | |
C22 | 0.3655 (2) | 0.84620 (14) | 0.60948 (15) | 0.0637 (5) | |
C23 | 0.4534 (2) | 0.87148 (14) | 0.52541 (16) | 0.0673 (5) | |
H23 | 0.444183 | 0.938028 | 0.488495 | 0.081* | |
C24 | 0.55390 (19) | 0.80070 (13) | 0.49508 (13) | 0.0566 (4) | |
H24 | 0.611932 | 0.819838 | 0.438259 | 0.068* | |
C25 | 0.2545 (3) | 0.9249 (2) | 0.6427 (2) | 0.1065 (10) | |
H25A | 0.213014 | 0.959960 | 0.589852 | 0.160* | |
H25B | 0.281923 | 0.972199 | 0.662035 | 0.160* | |
H25C | 0.198459 | 0.892328 | 0.697207 | 0.160* | |
C26 | 0.52270 (13) | 0.81733 (11) | 0.02227 (10) | 0.0380 (3) | |
C27 | 0.53883 (15) | 0.73810 (11) | −0.02741 (11) | 0.0425 (3) | |
C28 | 0.44133 (18) | 0.72885 (14) | −0.06096 (12) | 0.0541 (4) | |
H28 | 0.366042 | 0.775090 | −0.054226 | 0.065* | |
C29 | 0.4568 (2) | 0.65138 (17) | −0.10395 (15) | 0.0704 (6) | |
H29 | 0.391315 | 0.644228 | −0.124695 | 0.084* | |
C30 | 0.5697 (2) | 0.58434 (17) | −0.11614 (16) | 0.0773 (6) | |
H30 | 0.579713 | 0.532603 | −0.145751 | 0.093* | |
C31 | 0.6673 (2) | 0.59255 (14) | −0.08550 (14) | 0.0642 (5) | |
H31 | 0.743292 | 0.547740 | −0.095499 | 0.077* | |
C32 | 0.65154 (16) | 0.66868 (12) | −0.03921 (11) | 0.0466 (4) | |
C33 | 0.74921 (14) | 0.76072 (12) | 0.01846 (11) | 0.0425 (3) | |
H33 | 0.811056 | 0.738537 | 0.058444 | 0.051* | |
C34 | 0.62391 (13) | 0.80089 (10) | 0.07759 (10) | 0.0353 (3) | |
C35 | 0.61372 (13) | 0.89159 (10) | 0.11657 (10) | 0.0346 (3) | |
H35 | 0.586305 | 0.955024 | 0.070535 | 0.041* | |
C36 | 0.72907 (13) | 0.89408 (10) | 0.14622 (10) | 0.0350 (3) | |
C37 | 0.76963 (14) | 0.82115 (11) | 0.22526 (11) | 0.0406 (3) | |
H37 | 0.727948 | 0.769001 | 0.258268 | 0.049* | |
C38 | 0.87077 (14) | 0.82544 (12) | 0.25505 (11) | 0.0437 (3) | |
H38 | 0.897624 | 0.777030 | 0.307961 | 0.052* | |
C39 | 0.93090 (14) | 0.90306 (12) | 0.20459 (11) | 0.0440 (3) | |
C40 | 0.89462 (15) | 0.97603 (12) | 0.12563 (12) | 0.0458 (4) | |
H40 | 0.937658 | 1.027306 | 0.092445 | 0.055* | |
C41 | 0.79271 (14) | 0.97113 (11) | 0.09698 (11) | 0.0406 (3) | |
H41 | 0.766366 | 1.019984 | 0.044101 | 0.049* | |
C42 | 0.78724 (17) | 0.83952 (14) | −0.07436 (13) | 0.0570 (4) | |
H42A | 0.867909 | 0.812801 | −0.109343 | 0.085* | |
H42B | 0.789421 | 0.898954 | −0.057477 | 0.085* | |
H42C | 0.728397 | 0.856544 | −0.114837 | 0.085* | |
C43 | 0.51140 (13) | 0.87094 (10) | 0.20643 (10) | 0.0356 (3) | |
C44 | 0.43061 (13) | 0.94700 (11) | 0.25823 (11) | 0.0389 (3) | |
C45 | 0.46515 (16) | 1.03638 (12) | 0.24885 (13) | 0.0490 (4) | |
H45 | 0.541165 | 1.048068 | 0.209429 | 0.059* | |
C46 | 0.38805 (18) | 1.10767 (13) | 0.29729 (14) | 0.0572 (4) | |
H46 | 0.413516 | 1.166340 | 0.290698 | 0.069* | |
C47 | 0.27383 (17) | 1.09373 (14) | 0.35538 (14) | 0.0581 (5) | |
C48 | 0.23854 (17) | 1.00576 (16) | 0.36250 (15) | 0.0634 (5) | |
H48 | 0.161258 | 0.995375 | 0.400164 | 0.076* | |
C49 | 0.31503 (15) | 0.93341 (14) | 0.31522 (13) | 0.0521 (4) | |
H49 | 0.289006 | 0.875070 | 0.321568 | 0.063* | |
C50 | 0.1902 (2) | 1.17146 (19) | 0.40908 (19) | 0.0893 (7) | |
H50A | 0.204511 | 1.154431 | 0.473957 | 0.134* | |
H50B | 0.105262 | 1.172562 | 0.412870 | 0.134* | |
H50C | 0.207563 | 1.236831 | 0.374590 | 0.134* | |
N1 | 0.76748 (13) | 0.64877 (10) | 0.44746 (10) | 0.0468 (3) | |
N2 | 0.87729 (15) | 0.30507 (15) | 0.89270 (11) | 0.0638 (4) | |
N3 | 0.50112 (11) | 0.77822 (9) | 0.23520 (9) | 0.0402 (3) | |
N4 | 1.03716 (16) | 0.90838 (14) | 0.23749 (13) | 0.0704 (5) | |
O1 | 0.60250 (9) | 0.53733 (9) | 0.37823 (8) | 0.0499 (3) | |
O2 | 0.95481 (9) | 0.37380 (9) | 0.37996 (8) | 0.0501 (3) | |
O3 | 0.84776 (9) | 0.56013 (8) | 0.42149 (8) | 0.0463 (3) | |
O4 | 0.85062 (15) | 0.22382 (14) | 0.93883 (11) | 0.0900 (5) | |
O5 | 0.94819 (19) | 0.34191 (16) | 0.91234 (13) | 0.1043 (6) | |
O6 | 0.43257 (10) | 0.88679 (8) | 0.02632 (9) | 0.0499 (3) | |
O7 | 0.74976 (11) | 0.66992 (8) | −0.00674 (9) | 0.0509 (3) | |
O8 | 0.58807 (10) | 0.72448 (7) | 0.16663 (7) | 0.0404 (2) | |
O9 | 1.06326 (16) | 0.84887 (14) | 0.31079 (13) | 0.1002 (6) | |
O10 | 1.0951 (2) | 0.97103 (19) | 0.18936 (18) | 0.1604 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0335 (7) | 0.0356 (7) | 0.0364 (7) | −0.0062 (6) | −0.0071 (6) | −0.0045 (6) |
C2 | 0.0390 (7) | 0.0379 (7) | 0.0358 (7) | −0.0058 (6) | −0.0073 (6) | −0.0066 (6) |
C3 | 0.0542 (9) | 0.0471 (9) | 0.0401 (8) | 0.0006 (7) | −0.0155 (7) | −0.0061 (7) |
C4 | 0.0780 (13) | 0.0640 (11) | 0.0383 (9) | 0.0036 (10) | −0.0189 (9) | −0.0144 (8) |
C5 | 0.0712 (13) | 0.0766 (13) | 0.0453 (10) | 0.0061 (10) | −0.0070 (9) | −0.0259 (9) |
C6 | 0.0494 (10) | 0.0700 (12) | 0.0533 (10) | 0.0074 (8) | −0.0082 (8) | −0.0260 (9) |
C7 | 0.0395 (8) | 0.0469 (9) | 0.0400 (8) | −0.0043 (6) | −0.0086 (6) | −0.0126 (7) |
C8 | 0.0369 (7) | 0.0488 (9) | 0.0384 (8) | 0.0009 (6) | −0.0120 (6) | −0.0131 (7) |
C9 | 0.0317 (7) | 0.0386 (7) | 0.0356 (7) | −0.0092 (6) | −0.0056 (6) | −0.0075 (6) |
C10 | 0.0313 (6) | 0.0357 (7) | 0.0354 (7) | −0.0100 (5) | −0.0048 (5) | −0.0075 (6) |
C11 | 0.0330 (7) | 0.0369 (7) | 0.0335 (7) | −0.0092 (6) | −0.0035 (5) | −0.0101 (6) |
C12 | 0.0438 (8) | 0.0511 (9) | 0.0417 (8) | −0.0224 (7) | −0.0058 (7) | −0.0085 (7) |
C13 | 0.0432 (8) | 0.0671 (11) | 0.0462 (9) | −0.0174 (8) | −0.0111 (7) | −0.0195 (8) |
C14 | 0.0445 (8) | 0.0567 (10) | 0.0336 (8) | −0.0023 (7) | −0.0088 (6) | −0.0141 (7) |
C15 | 0.0490 (9) | 0.0481 (9) | 0.0367 (8) | −0.0149 (7) | −0.0041 (7) | −0.0027 (7) |
C16 | 0.0376 (7) | 0.0451 (8) | 0.0394 (8) | −0.0161 (6) | −0.0054 (6) | −0.0071 (6) |
C17 | 0.0674 (11) | 0.0400 (9) | 0.0477 (9) | −0.0034 (8) | −0.0174 (8) | −0.0067 (7) |
C18 | 0.0452 (8) | 0.0370 (7) | 0.0352 (7) | −0.0119 (6) | −0.0078 (6) | −0.0066 (6) |
C19 | 0.0506 (9) | 0.0374 (8) | 0.0393 (8) | −0.0070 (7) | −0.0137 (7) | −0.0104 (6) |
C20 | 0.0561 (10) | 0.0443 (9) | 0.0448 (9) | −0.0032 (7) | −0.0102 (7) | −0.0103 (7) |
C21 | 0.0608 (11) | 0.0646 (12) | 0.0488 (10) | 0.0025 (9) | −0.0099 (8) | −0.0227 (9) |
C22 | 0.0754 (13) | 0.0543 (11) | 0.0639 (12) | 0.0133 (9) | −0.0297 (10) | −0.0292 (9) |
C23 | 0.0902 (15) | 0.0396 (9) | 0.0699 (13) | 0.0016 (9) | −0.0311 (12) | −0.0119 (9) |
C24 | 0.0722 (12) | 0.0413 (9) | 0.0519 (10) | −0.0091 (8) | −0.0155 (9) | −0.0062 (8) |
C25 | 0.112 (2) | 0.0837 (17) | 0.106 (2) | 0.0373 (15) | −0.0270 (17) | −0.0469 (16) |
C26 | 0.0407 (8) | 0.0341 (7) | 0.0365 (7) | −0.0111 (6) | −0.0106 (6) | −0.0003 (6) |
C27 | 0.0535 (9) | 0.0424 (8) | 0.0336 (7) | −0.0158 (7) | −0.0121 (7) | −0.0045 (6) |
C28 | 0.0623 (11) | 0.0620 (11) | 0.0444 (9) | −0.0198 (9) | −0.0188 (8) | −0.0094 (8) |
C29 | 0.0932 (16) | 0.0805 (14) | 0.0586 (11) | −0.0307 (12) | −0.0320 (11) | −0.0214 (10) |
C30 | 0.1142 (19) | 0.0693 (13) | 0.0666 (13) | −0.0174 (13) | −0.0323 (13) | −0.0326 (11) |
C31 | 0.0874 (14) | 0.0557 (11) | 0.0537 (11) | −0.0046 (10) | −0.0203 (10) | −0.0245 (9) |
C32 | 0.0604 (10) | 0.0428 (8) | 0.0359 (8) | −0.0109 (7) | −0.0120 (7) | −0.0075 (7) |
C33 | 0.0407 (8) | 0.0419 (8) | 0.0450 (8) | −0.0058 (6) | −0.0115 (7) | −0.0114 (7) |
C34 | 0.0386 (7) | 0.0301 (7) | 0.0350 (7) | −0.0084 (6) | −0.0101 (6) | −0.0019 (6) |
C35 | 0.0360 (7) | 0.0295 (7) | 0.0372 (7) | −0.0088 (5) | −0.0114 (6) | −0.0020 (6) |
C36 | 0.0345 (7) | 0.0338 (7) | 0.0365 (7) | −0.0086 (6) | −0.0078 (6) | −0.0070 (6) |
C37 | 0.0426 (8) | 0.0365 (7) | 0.0415 (8) | −0.0141 (6) | −0.0127 (6) | 0.0007 (6) |
C38 | 0.0440 (8) | 0.0444 (8) | 0.0400 (8) | −0.0104 (7) | −0.0142 (7) | −0.0007 (7) |
C39 | 0.0383 (8) | 0.0520 (9) | 0.0453 (8) | −0.0153 (7) | −0.0130 (7) | −0.0082 (7) |
C40 | 0.0462 (8) | 0.0464 (9) | 0.0460 (9) | −0.0226 (7) | −0.0094 (7) | −0.0021 (7) |
C41 | 0.0434 (8) | 0.0373 (8) | 0.0388 (8) | −0.0122 (6) | −0.0118 (6) | 0.0001 (6) |
C42 | 0.0566 (10) | 0.0591 (11) | 0.0499 (10) | −0.0184 (8) | 0.0016 (8) | −0.0124 (8) |
C43 | 0.0342 (7) | 0.0353 (7) | 0.0397 (7) | −0.0105 (6) | −0.0124 (6) | −0.0054 (6) |
C44 | 0.0370 (7) | 0.0392 (8) | 0.0425 (8) | −0.0069 (6) | −0.0137 (6) | −0.0095 (6) |
C45 | 0.0486 (9) | 0.0418 (8) | 0.0582 (10) | −0.0117 (7) | −0.0094 (8) | −0.0148 (7) |
C46 | 0.0646 (11) | 0.0438 (9) | 0.0684 (12) | −0.0050 (8) | −0.0210 (9) | −0.0208 (8) |
C47 | 0.0550 (10) | 0.0566 (11) | 0.0634 (11) | 0.0103 (8) | −0.0245 (9) | −0.0250 (9) |
C48 | 0.0395 (9) | 0.0773 (13) | 0.0705 (12) | −0.0049 (9) | −0.0051 (8) | −0.0274 (10) |
C49 | 0.0412 (8) | 0.0539 (10) | 0.0641 (11) | −0.0128 (7) | −0.0089 (8) | −0.0185 (8) |
C50 | 0.0798 (15) | 0.0837 (16) | 0.1007 (18) | 0.0227 (12) | −0.0250 (13) | −0.0491 (14) |
N1 | 0.0513 (8) | 0.0419 (7) | 0.0457 (7) | −0.0175 (6) | −0.0037 (6) | −0.0079 (6) |
N2 | 0.0560 (9) | 0.0849 (12) | 0.0437 (8) | 0.0007 (8) | −0.0156 (7) | −0.0160 (8) |
N3 | 0.0422 (7) | 0.0383 (7) | 0.0400 (7) | −0.0119 (5) | −0.0073 (5) | −0.0079 (5) |
N4 | 0.0658 (10) | 0.0810 (12) | 0.0736 (11) | −0.0375 (9) | −0.0357 (9) | 0.0068 (9) |
O1 | 0.0344 (5) | 0.0627 (7) | 0.0452 (6) | 0.0009 (5) | −0.0107 (5) | −0.0114 (5) |
O2 | 0.0335 (5) | 0.0671 (7) | 0.0467 (6) | 0.0048 (5) | −0.0110 (5) | −0.0217 (6) |
O3 | 0.0390 (6) | 0.0497 (6) | 0.0490 (6) | −0.0186 (5) | 0.0026 (5) | −0.0132 (5) |
O4 | 0.0839 (11) | 0.0959 (12) | 0.0638 (9) | −0.0095 (9) | −0.0254 (8) | 0.0176 (9) |
O5 | 0.1184 (14) | 0.1341 (16) | 0.0819 (11) | −0.0263 (12) | −0.0629 (11) | −0.0194 (11) |
O6 | 0.0460 (6) | 0.0428 (6) | 0.0627 (7) | −0.0033 (5) | −0.0236 (5) | −0.0102 (5) |
O7 | 0.0531 (7) | 0.0428 (6) | 0.0575 (7) | −0.0001 (5) | −0.0162 (5) | −0.0187 (5) |
O8 | 0.0507 (6) | 0.0296 (5) | 0.0380 (5) | −0.0095 (4) | −0.0095 (5) | −0.0035 (4) |
O9 | 0.0981 (12) | 0.1161 (13) | 0.0996 (12) | −0.0536 (11) | −0.0689 (10) | 0.0269 (10) |
O10 | 0.161 (2) | 0.188 (2) | 0.1607 (19) | −0.1428 (19) | −0.1137 (17) | 0.0853 (17) |
C1—O1 | 1.2141 (17) | C27—C32 | 1.395 (2) |
C1—C2 | 1.468 (2) | C27—C28 | 1.400 (2) |
C1—C9 | 1.538 (2) | C28—C29 | 1.378 (3) |
C2—C7 | 1.396 (2) | C28—H28 | 0.9300 |
C2—C3 | 1.399 (2) | C29—C30 | 1.382 (3) |
C3—C4 | 1.369 (2) | C29—H29 | 0.9300 |
C3—H3 | 0.9300 | C30—C31 | 1.369 (3) |
C4—C5 | 1.381 (3) | C30—H30 | 0.9300 |
C4—H4 | 0.9300 | C31—C32 | 1.393 (2) |
C5—C6 | 1.376 (3) | C31—H31 | 0.9300 |
C5—H5 | 0.9300 | C32—O7 | 1.354 (2) |
C6—C7 | 1.387 (2) | C33—O7 | 1.4471 (18) |
C6—H6 | 0.9300 | C33—C34 | 1.514 (2) |
C7—O2 | 1.3649 (18) | C33—C42 | 1.521 (2) |
C8—O2 | 1.4495 (18) | C33—H33 | 0.9754 |
C8—C17 | 1.513 (2) | C34—O8 | 1.4636 (16) |
C8—C9 | 1.518 (2) | C34—C35 | 1.5288 (19) |
C8—H8 | 0.9943 | C35—C43 | 1.514 (2) |
C9—O3 | 1.4598 (17) | C35—C36 | 1.5243 (19) |
C9—C10 | 1.5353 (19) | C35—H35 | 0.9800 |
C10—C18 | 1.5187 (19) | C36—C41 | 1.3891 (19) |
C10—C11 | 1.5199 (19) | C36—C37 | 1.395 (2) |
C10—H10 | 0.9800 | C37—C38 | 1.379 (2) |
C11—C16 | 1.3895 (19) | C37—H37 | 0.9300 |
C11—C12 | 1.392 (2) | C38—C39 | 1.374 (2) |
C12—C13 | 1.383 (2) | C38—H38 | 0.9300 |
C12—H12 | 0.9300 | C39—C40 | 1.377 (2) |
C13—C14 | 1.374 (2) | C39—N4 | 1.466 (2) |
C13—H13 | 0.9300 | C40—C41 | 1.381 (2) |
C14—C15 | 1.379 (2) | C40—H40 | 0.9300 |
C14—N2 | 1.474 (2) | C41—H41 | 0.9300 |
C15—C16 | 1.385 (2) | C42—H42A | 0.9600 |
C15—H15 | 0.9300 | C42—H42B | 0.9600 |
C16—H16 | 0.9300 | C42—H42C | 0.9600 |
C17—H17A | 0.9600 | C43—N3 | 1.2855 (18) |
C17—H17B | 0.9600 | C43—C44 | 1.467 (2) |
C17—H17C | 0.9600 | C44—C49 | 1.387 (2) |
C18—N1 | 1.2833 (19) | C44—C45 | 1.394 (2) |
C18—C19 | 1.462 (2) | C45—C46 | 1.378 (2) |
C19—C20 | 1.387 (2) | C45—H45 | 0.9300 |
C19—C24 | 1.400 (2) | C46—C47 | 1.380 (3) |
C20—C21 | 1.385 (2) | C46—H46 | 0.9300 |
C20—H20 | 0.9300 | C47—C48 | 1.388 (3) |
C21—C22 | 1.380 (3) | C47—C50 | 1.509 (3) |
C21—H21 | 0.9300 | C48—C49 | 1.378 (3) |
C22—C23 | 1.380 (3) | C48—H48 | 0.9300 |
C22—C25 | 1.516 (3) | C49—H49 | 0.9300 |
C23—C24 | 1.371 (3) | C50—H50A | 0.9600 |
C23—H23 | 0.9300 | C50—H50B | 0.9600 |
C24—H24 | 0.9300 | C50—H50C | 0.9600 |
C25—H25A | 0.9600 | N1—O3 | 1.4245 (17) |
C25—H25B | 0.9600 | N2—O5 | 1.222 (2) |
C25—H25C | 0.9600 | N2—O4 | 1.222 (2) |
C26—O6 | 1.2174 (17) | N3—O8 | 1.4389 (16) |
C26—C27 | 1.466 (2) | N4—O10 | 1.193 (2) |
C26—C34 | 1.532 (2) | N4—O9 | 1.205 (2) |
O1—C1—C2 | 123.70 (13) | C29—C28—C27 | 120.12 (19) |
O1—C1—C9 | 121.97 (13) | C29—C28—H28 | 119.9 |
C2—C1—C9 | 114.30 (12) | C27—C28—H28 | 119.9 |
C7—C2—C3 | 118.94 (14) | C28—C29—C30 | 119.80 (19) |
C7—C2—C1 | 119.87 (13) | C28—C29—H29 | 120.1 |
C3—C2—C1 | 121.19 (13) | C30—C29—H29 | 120.1 |
C4—C3—C2 | 120.46 (16) | C31—C30—C29 | 121.33 (18) |
C4—C3—H3 | 119.8 | C31—C30—H30 | 119.3 |
C2—C3—H3 | 119.8 | C29—C30—H30 | 119.3 |
C3—C4—C5 | 119.97 (17) | C30—C31—C32 | 119.34 (19) |
C3—C4—H4 | 120.0 | C30—C31—H31 | 120.3 |
C5—C4—H4 | 120.0 | C32—C31—H31 | 120.3 |
C6—C5—C4 | 120.87 (17) | O7—C32—C31 | 116.44 (16) |
C6—C5—H5 | 119.6 | O7—C32—C27 | 123.28 (14) |
C4—C5—H5 | 119.6 | C31—C32—C27 | 120.28 (17) |
C5—C6—C7 | 119.52 (16) | O7—C33—C34 | 111.37 (12) |
C5—C6—H6 | 120.2 | O7—C33—C42 | 109.51 (13) |
C7—C6—H6 | 120.2 | C34—C33—C42 | 111.25 (13) |
O2—C7—C6 | 117.00 (14) | O7—C33—H33 | 103.8 |
O2—C7—C2 | 122.76 (13) | C34—C33—H33 | 109.9 |
C6—C7—C2 | 120.23 (15) | C42—C33—H33 | 110.9 |
O2—C8—C17 | 110.12 (13) | O8—C34—C33 | 110.83 (11) |
O2—C8—C9 | 109.52 (12) | O8—C34—C35 | 103.02 (11) |
C17—C8—C9 | 112.49 (13) | C33—C34—C35 | 116.73 (12) |
O2—C8—H8 | 103.9 | O8—C34—C26 | 102.43 (10) |
C17—C8—H8 | 110.1 | C33—C34—C26 | 110.00 (12) |
C9—C8—H8 | 110.3 | C35—C34—C26 | 112.65 (11) |
O3—C9—C8 | 108.26 (11) | C43—C35—C36 | 110.13 (11) |
O3—C9—C10 | 103.38 (11) | C43—C35—C34 | 98.22 (11) |
C8—C9—C10 | 118.42 (12) | C36—C35—C34 | 115.46 (11) |
O3—C9—C1 | 104.48 (11) | C43—C35—H35 | 110.8 |
C8—C9—C1 | 109.41 (12) | C36—C35—H35 | 110.8 |
C10—C9—C1 | 111.76 (11) | C34—C35—H35 | 110.8 |
C18—C10—C11 | 113.03 (11) | C41—C36—C37 | 119.08 (13) |
C18—C10—C9 | 97.56 (11) | C41—C36—C35 | 120.38 (12) |
C11—C10—C9 | 114.07 (11) | C37—C36—C35 | 120.50 (12) |
C18—C10—H10 | 110.5 | C38—C37—C36 | 120.79 (13) |
C11—C10—H10 | 110.5 | C38—C37—H37 | 119.6 |
C9—C10—H10 | 110.5 | C36—C37—H37 | 119.6 |
C16—C11—C12 | 118.93 (13) | C39—C38—C37 | 118.32 (14) |
C16—C11—C10 | 119.63 (12) | C39—C38—H38 | 120.8 |
C12—C11—C10 | 121.31 (12) | C37—C38—H38 | 120.8 |
C13—C12—C11 | 120.70 (14) | C38—C39—C40 | 122.75 (14) |
C13—C12—H12 | 119.7 | C38—C39—N4 | 118.18 (14) |
C11—C12—H12 | 119.7 | C40—C39—N4 | 119.06 (14) |
C14—C13—C12 | 118.80 (14) | C39—C40—C41 | 118.30 (14) |
C14—C13—H13 | 120.6 | C39—C40—H40 | 120.9 |
C12—C13—H13 | 120.6 | C41—C40—H40 | 120.9 |
C13—C14—C15 | 122.21 (14) | C40—C41—C36 | 120.76 (14) |
C13—C14—N2 | 118.79 (15) | C40—C41—H41 | 119.6 |
C15—C14—N2 | 119.01 (16) | C36—C41—H41 | 119.6 |
C14—C15—C16 | 118.38 (14) | C33—C42—H42A | 109.5 |
C14—C15—H15 | 120.8 | C33—C42—H42B | 109.5 |
C16—C15—H15 | 120.8 | H42A—C42—H42B | 109.5 |
C15—C16—C11 | 120.93 (14) | C33—C42—H42C | 109.5 |
C15—C16—H16 | 119.5 | H42A—C42—H42C | 109.5 |
C11—C16—H16 | 119.5 | H42B—C42—H42C | 109.5 |
C8—C17—H17A | 109.5 | N3—C43—C44 | 121.72 (13) |
C8—C17—H17B | 109.5 | N3—C43—C35 | 113.51 (13) |
H17A—C17—H17B | 109.5 | C44—C43—C35 | 124.77 (12) |
C8—C17—H17C | 109.5 | C49—C44—C45 | 118.06 (15) |
H17A—C17—H17C | 109.5 | C49—C44—C43 | 120.57 (14) |
H17B—C17—H17C | 109.5 | C45—C44—C43 | 121.32 (14) |
N1—C18—C19 | 121.23 (13) | C46—C45—C44 | 120.82 (16) |
N1—C18—C10 | 113.52 (13) | C46—C45—H45 | 119.6 |
C19—C18—C10 | 125.20 (13) | C44—C45—H45 | 119.6 |
C20—C19—C24 | 118.06 (15) | C45—C46—C47 | 121.32 (17) |
C20—C19—C18 | 121.30 (14) | C45—C46—H46 | 119.3 |
C24—C19—C18 | 120.53 (15) | C47—C46—H46 | 119.3 |
C21—C20—C19 | 120.48 (16) | C46—C47—C48 | 117.63 (16) |
C21—C20—H20 | 119.8 | C46—C47—C50 | 121.2 (2) |
C19—C20—H20 | 119.8 | C48—C47—C50 | 121.2 (2) |
C22—C21—C20 | 121.21 (18) | C49—C48—C47 | 121.71 (17) |
C22—C21—H21 | 119.4 | C49—C48—H48 | 119.1 |
C20—C21—H21 | 119.4 | C47—C48—H48 | 119.1 |
C23—C22—C21 | 118.18 (17) | C48—C49—C44 | 120.43 (17) |
C23—C22—C25 | 121.2 (2) | C48—C49—H49 | 119.8 |
C21—C22—C25 | 120.6 (2) | C44—C49—H49 | 119.8 |
C24—C23—C22 | 121.48 (18) | C47—C50—H50A | 109.5 |
C24—C23—H23 | 119.3 | C47—C50—H50B | 109.5 |
C22—C23—H23 | 119.3 | H50A—C50—H50B | 109.5 |
C23—C24—C19 | 120.58 (18) | C47—C50—H50C | 109.5 |
C23—C24—H24 | 119.7 | H50A—C50—H50C | 109.5 |
C19—C24—H24 | 119.7 | H50B—C50—H50C | 109.5 |
C22—C25—H25A | 109.5 | C18—N1—O3 | 108.80 (12) |
C22—C25—H25B | 109.5 | O5—N2—O4 | 123.94 (18) |
H25A—C25—H25B | 109.5 | O5—N2—C14 | 117.70 (18) |
C22—C25—H25C | 109.5 | O4—N2—C14 | 118.34 (17) |
H25A—C25—H25C | 109.5 | C43—N3—O8 | 108.27 (11) |
H25B—C25—H25C | 109.5 | O10—N4—O9 | 122.85 (17) |
O6—C26—C27 | 123.78 (14) | O10—N4—C39 | 118.15 (16) |
O6—C26—C34 | 121.71 (13) | O9—N4—C39 | 118.99 (15) |
C27—C26—C34 | 114.29 (12) | C7—O2—C8 | 116.92 (11) |
C32—C27—C28 | 119.08 (15) | N1—O3—C9 | 106.63 (10) |
C32—C27—C26 | 119.90 (14) | C32—O7—C33 | 117.78 (12) |
C28—C27—C26 | 120.99 (15) | N3—O8—C34 | 106.52 (9) |
Cg1 and Cg2 are the centroids of the C44–C49 and C11–C16 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···O1i | 0.98 | 2.40 | 3.3466 (17) | 162 |
C35—H35···O6ii | 0.98 | 2.25 | 3.2072 (17) | 164 |
C16—H16···N3i | 0.93 | 2.56 | 3.3091 (19) | 138 |
C23—H23···Cg1 | 0.93 | 2.95 | 3.581 (2) | 127 |
C30—H30···Cg2iii | 0.93 | 3.00 | 3.758 (2) | 140 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z; (iii) x, y, z−1. |
Acknowledgements
The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.
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