organic compounds
Ethyl 2-[9-(5-bromo-2-hydroxyphenyl)-3,3,6,6-tetramethyl-1,8-dioxo-1,2,3,4,5,6,7,8,9,10-decahydroacridin-10-yl]acetate
aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, cUniversity of Ondokuzmayıs, Science Faculty, Department of Physics, Samsun, Turkey, dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, eChemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and fKirkuk University, College of Education, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com
In the title compound, C27H32BrNO5, the central 1,4-dihydropyridine ring adopts a shallow sofa conformation (with the C atom bearing the bromophenol ring as the flap), whereas the pendant cyclohexene rings both have twisted-boat conformations. The molecule features an intramolecular O—H⋯O hydrogen bond, which closes an S(8) ring. In the crystal, molecules are linked by C—H⋯O interactions, forming C(12) chains along the c-axis direction. The ethyl acetate grouping is disordered over two sets of sites in a 0.719 (11):0.281 (11) ratio.
Keywords: crystal structure; acridines; acetic acid; hydrogen bonding; sofa conformation; disorder.
CCDC reference: 1530927
Structure description
Acridine derivatives have been used as anti-malarial (Santelli-Rouvier et al., 2004) anti-bacterial (Wainwright, 2001), anti-leishmanial (Delmas et al., 2004) and anti-HIV (Hamy et al., 1998) agents. They also have exhibited excellent results in chemotherapy of cancer (Cholody et al., 1996; Rewcastle et al., 1986). As part of our studies in this area, we report herein the synthesis and of the title compound (Fig. 1).
The central 1,4-dihydropyridine ring (N1/C7/C8/C13/C16/C17) of the 1,2,3,4,5,6,7,8,9,10-decahydroacridine ring system (N1/C7–C13/C16–C21) adopts a shallow sofa conformation [the puckering parameters are QT = 0.229 (3) Å, θ = 66.4 (8)°, φ = 191.6 (8)°], while the cyclohexene rings (C8–C13 and C16–C21) of the 1,2,3,4,5,6,7,8,9,10-decahydroacridine ring system have a twisted-boat conformation [the puckering parameters are QT = 0.472 (4) Å, θ = 123.9 (4)°, φ = 341.3 (5)° and QT = 0.501 (4) Å, θ = 119.7 (5)°, φ = 46.4 (5)°, respectively]. The bond lengths and bond angles in the title compound are normal and comparable to those observed in similar structures (Akkurt et al., 2015).
In the crystal, adjacent molecules are connected by C—H⋯O interactions, forming C(12) chains along the c-axis direction (Table 1, Fig. 2).
Synthesis and crystallization
A mixture of dimedone (1.12 g, 0.008 mol), 5-bromo-2-hydroxybenzaldhyde (0.81 g; 0.004 mol), ethyl glycinate hydrochloride (0.56 g; 0.004 mol) and triethylamine (1.12 ml; 0.008 mol) in 30 ml ethanol was refluxed for 5 h. The solid product was deposited on cooling and collected by filtration under vacuum. Recrystallization of the crude product from ethanol afforded light-yellow prisms in 58% yield (m.p. 485 K).
Refinement
Crystal data, data collection and structure . The title molecule exhibits disorder of the ethyl acetate group. The atoms of the ethyl acetate group were fixed with restraints (EADP and SADI commands) and had to be split over two positions. The occupancies refined to 0.719 (11):0.281 (11).
details are summarized in Table 2Structural data
CCDC reference: 1530927
https://doi.org/10.1107/S2414314617005739/hb4135sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617005739/hb4135Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617005739/hb4135Isup3.cml
Data collection: X-AREA (Stoe & Cie, 2002); cell
X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).C27H32BrNO5 | F(000) = 1104 |
Mr = 530.44 | Dx = 1.349 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.1174 (5) Å | Cell parameters from 14005 reflections |
b = 19.0567 (8) Å | θ = 1.5–26.5° |
c = 14.0387 (7) Å | µ = 1.61 mm−1 |
β = 105.254 (4)° | T = 296 K |
V = 2611.4 (2) Å3 | Prism, light yellow |
Z = 4 | 0.67 × 0.51 × 0.38 mm |
Stoe IPDS 2 diffractometer | 5086 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 3086 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.058 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 1.9° |
rotation method scans | h = −12→12 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −21→23 |
Tmin = 0.425, Tmax = 0.620 | l = −17→17 |
15096 measured reflections |
Refinement on F2 | 8 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.0481P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max = 0.001 |
5086 reflections | Δρmax = 0.21 e Å−3 |
335 parameters | Δρmin = −0.27 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 | Occ. (<1) | |
C1 | 0.6851 (3) | 0.67758 (15) | 0.4523 (2) | 0.0586 (7) | |
H1 | 0.6899 | 0.6767 | 0.3870 | 0.070* | |
C2 | 0.7688 (3) | 0.63487 (16) | 0.5199 (2) | 0.0633 (7) | |
C3 | 0.7638 (3) | 0.63521 (17) | 0.6172 (2) | 0.0709 (8) | |
H3 | 0.8229 | 0.6070 | 0.6635 | 0.085* | |
C4 | 0.6711 (3) | 0.67753 (18) | 0.6447 (2) | 0.0691 (8) | |
H4 | 0.6663 | 0.6774 | 0.7100 | 0.083* | |
C5 | 0.5848 (3) | 0.72029 (16) | 0.5770 (2) | 0.0624 (7) | |
C6 | 0.5930 (3) | 0.72224 (15) | 0.47920 (19) | 0.0556 (7) | |
C7 | 0.4953 (3) | 0.76780 (15) | 0.40186 (19) | 0.0576 (7) | |
H7 | 0.4575 | 0.8044 | 0.4361 | 0.069* | |
C8 | 0.5669 (3) | 0.80239 (15) | 0.33324 (19) | 0.0573 (7) | |
C9 | 0.6446 (3) | 0.86548 (16) | 0.3689 (2) | 0.0678 (8) | |
C10 | 0.7075 (4) | 0.90358 (18) | 0.2990 (3) | 0.0831 (10) | |
H10A | 0.7826 | 0.9323 | 0.3362 | 0.100* | |
H10B | 0.6398 | 0.9345 | 0.2580 | 0.100* | |
C11 | 0.7607 (3) | 0.85355 (17) | 0.2335 (2) | 0.0711 (8) | |
C12 | 0.6438 (3) | 0.80649 (17) | 0.17857 (19) | 0.0651 (8) | |
H12A | 0.5841 | 0.8334 | 0.1258 | 0.078* | |
H12B | 0.6817 | 0.7682 | 0.1485 | 0.078* | |
C13 | 0.5594 (3) | 0.77610 (15) | 0.24226 (19) | 0.0579 (7) | |
C14 | 0.8774 (4) | 0.8090 (2) | 0.2974 (2) | 0.0864 (10) | |
H14A | 0.9124 | 0.7782 | 0.2558 | 0.130* | |
H14B | 0.8432 | 0.7819 | 0.3434 | 0.130* | |
H14C | 0.9494 | 0.8393 | 0.3329 | 0.130* | |
C15 | 0.8154 (4) | 0.8958 (2) | 0.1583 (3) | 0.0936 (11) | |
H15A | 0.8504 | 0.8641 | 0.1177 | 0.140* | |
H15B | 0.8874 | 0.9264 | 0.1929 | 0.140* | |
H15C | 0.7424 | 0.9231 | 0.1176 | 0.140* | |
C16 | 0.3809 (3) | 0.69497 (15) | 0.2560 (2) | 0.0597 (7) | |
C17 | 0.3801 (3) | 0.72313 (15) | 0.3446 (2) | 0.0599 (7) | |
C18 | 0.2692 (3) | 0.70791 (17) | 0.3893 (2) | 0.0681 (8) | |
C19 | 0.1600 (4) | 0.6585 (2) | 0.3369 (3) | 0.0856 (10) | |
H19A | 0.0894 | 0.6846 | 0.2902 | 0.103* | |
H19B | 0.1184 | 0.6369 | 0.3845 | 0.103* | |
C20 | 0.2158 (4) | 0.6014 (2) | 0.2822 (3) | 0.0835 (10) | |
C21 | 0.2848 (3) | 0.63714 (17) | 0.2098 (2) | 0.0748 (9) | |
H21A | 0.3352 | 0.6022 | 0.1834 | 0.090* | |
H21B | 0.2145 | 0.6562 | 0.1551 | 0.090* | |
C22 | 0.3184 (5) | 0.55518 (19) | 0.3538 (3) | 0.1046 (12) | |
H22A | 0.3510 | 0.5193 | 0.3178 | 0.157* | |
H22B | 0.2746 | 0.5339 | 0.3996 | 0.157* | |
H22C | 0.3941 | 0.5832 | 0.3894 | 0.157* | |
C23 | 0.0952 (5) | 0.5564 (3) | 0.2230 (3) | 0.1238 (16) | |
H23A | 0.0337 | 0.5853 | 0.1751 | 0.186* | |
H23B | 0.0473 | 0.5365 | 0.2671 | 0.186* | |
H23C | 0.1297 | 0.5194 | 0.1897 | 0.186* | |
C24 | 0.454 (5) | 0.695 (3) | 0.1031 (19) | 0.065 (2) | 0.281 (11) |
H24A | 0.4673 | 0.7323 | 0.0601 | 0.078* | 0.281 (11) |
H24B | 0.3628 | 0.6749 | 0.0771 | 0.078* | 0.281 (11) |
C25 | 0.562 (10) | 0.639 (3) | 0.114 (2) | 0.085 (4) | 0.281 (11) |
C26 | 0.641 (2) | 0.5489 (14) | 0.004 (2) | 0.120 (4) | 0.281 (11) |
H26A | 0.6698 | 0.5160 | 0.0585 | 0.144* | 0.281 (11) |
H26B | 0.5872 | 0.5235 | −0.0527 | 0.144* | 0.281 (11) |
C27 | 0.760 (3) | 0.5801 (14) | −0.019 (2) | 0.174 (4) | 0.281 (11) |
H27A | 0.8091 | 0.6083 | 0.0362 | 0.261* | 0.281 (11) |
H27B | 0.7316 | 0.6089 | −0.0763 | 0.261* | 0.281 (11) |
H27C | 0.8195 | 0.5436 | −0.0304 | 0.261* | 0.281 (11) |
O4 | 0.604 (2) | 0.5960 (14) | 0.1773 (15) | 0.132 (3) | 0.281 (11) |
O5 | 0.556 (3) | 0.6046 (13) | 0.032 (2) | 0.089 (2) | 0.281 (11) |
C24A | 0.4786 (15) | 0.6889 (11) | 0.1105 (7) | 0.065 (2) | 0.719 (11) |
H24C | 0.4938 | 0.7264 | 0.0679 | 0.078* | 0.719 (11) |
H24D | 0.3901 | 0.6683 | 0.0797 | 0.078* | 0.719 (11) |
C25A | 0.587 (3) | 0.6342 (13) | 0.1170 (7) | 0.085 (4) | 0.719 (11) |
C26A | 0.7064 (12) | 0.5693 (6) | 0.0292 (6) | 0.120 (4) | 0.719 (11) |
H26D | 0.6916 | 0.5251 | 0.0590 | 0.144* | 0.719 (11) |
H26E | 0.7930 | 0.5889 | 0.0667 | 0.144* | 0.719 (11) |
C27A | 0.7075 (12) | 0.5587 (6) | −0.0742 (7) | 0.174 (4) | 0.719 (11) |
H27D | 0.6313 | 0.5298 | −0.1066 | 0.261* | 0.719 (11) |
H27E | 0.7914 | 0.5362 | −0.0767 | 0.261* | 0.719 (11) |
H27F | 0.7005 | 0.6033 | −0.1070 | 0.261* | 0.719 (11) |
O4A | 0.6676 (9) | 0.6200 (5) | 0.1941 (5) | 0.132 (3) | 0.719 (11) |
O5A | 0.5942 (10) | 0.6180 (4) | 0.0276 (8) | 0.089 (2) | 0.719 (11) |
Br1 | 0.89080 (4) | 0.57315 (2) | 0.48022 (3) | 0.08792 (16) | |
N1 | 0.4734 (2) | 0.71957 (12) | 0.20561 (15) | 0.0603 (6) | |
O1 | 0.4932 (2) | 0.76108 (14) | 0.60854 (15) | 0.0786 (7) | |
H1A | 0.420 (4) | 0.762 (2) | 0.565 (3) | 0.118* | |
O2 | 0.2634 (2) | 0.73668 (13) | 0.46674 (17) | 0.0816 (6) | |
O3 | 0.6568 (3) | 0.88686 (13) | 0.45337 (17) | 0.0911 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0626 (18) | 0.0575 (17) | 0.0548 (15) | 0.0010 (15) | 0.0141 (14) | −0.0010 (14) |
C2 | 0.0578 (18) | 0.0571 (18) | 0.0705 (19) | −0.0048 (15) | 0.0087 (15) | −0.0001 (15) |
C3 | 0.067 (2) | 0.067 (2) | 0.068 (2) | −0.0044 (17) | −0.0001 (16) | 0.0139 (16) |
C4 | 0.073 (2) | 0.080 (2) | 0.0511 (16) | −0.0107 (18) | 0.0110 (16) | 0.0057 (16) |
C5 | 0.0654 (19) | 0.0663 (18) | 0.0564 (17) | −0.0062 (16) | 0.0179 (15) | −0.0036 (15) |
C6 | 0.0579 (17) | 0.0582 (17) | 0.0498 (15) | −0.0010 (14) | 0.0124 (13) | 0.0000 (13) |
C7 | 0.0654 (18) | 0.0585 (17) | 0.0518 (15) | 0.0095 (15) | 0.0203 (14) | 0.0009 (13) |
C8 | 0.0649 (18) | 0.0553 (17) | 0.0521 (15) | 0.0086 (14) | 0.0158 (14) | 0.0039 (13) |
C9 | 0.077 (2) | 0.0612 (19) | 0.0700 (19) | 0.0064 (16) | 0.0273 (17) | −0.0022 (15) |
C10 | 0.100 (3) | 0.067 (2) | 0.093 (2) | −0.0124 (19) | 0.044 (2) | −0.0077 (18) |
C11 | 0.079 (2) | 0.0732 (19) | 0.0671 (18) | 0.0019 (18) | 0.0300 (18) | 0.0015 (16) |
C12 | 0.073 (2) | 0.0708 (19) | 0.0525 (16) | 0.0077 (16) | 0.0182 (15) | 0.0091 (14) |
C13 | 0.0614 (17) | 0.0580 (17) | 0.0531 (16) | 0.0110 (15) | 0.0129 (13) | 0.0073 (13) |
C14 | 0.071 (2) | 0.116 (3) | 0.073 (2) | 0.008 (2) | 0.0203 (18) | 0.004 (2) |
C15 | 0.108 (3) | 0.093 (3) | 0.093 (2) | −0.006 (2) | 0.050 (2) | 0.009 (2) |
C16 | 0.0594 (18) | 0.0567 (17) | 0.0592 (17) | 0.0073 (14) | 0.0086 (15) | 0.0047 (14) |
C17 | 0.0608 (18) | 0.0624 (18) | 0.0549 (16) | 0.0063 (15) | 0.0127 (14) | 0.0052 (14) |
C18 | 0.0604 (19) | 0.070 (2) | 0.071 (2) | 0.0071 (16) | 0.0129 (16) | 0.0098 (16) |
C19 | 0.070 (2) | 0.099 (3) | 0.086 (2) | −0.004 (2) | 0.0196 (19) | 0.010 (2) |
C20 | 0.082 (2) | 0.077 (2) | 0.087 (2) | −0.018 (2) | 0.015 (2) | 0.0003 (19) |
C21 | 0.077 (2) | 0.069 (2) | 0.0719 (19) | 0.0017 (18) | 0.0086 (17) | −0.0008 (16) |
C22 | 0.125 (3) | 0.075 (3) | 0.110 (3) | 0.000 (2) | 0.025 (3) | 0.018 (2) |
C23 | 0.116 (3) | 0.120 (4) | 0.134 (4) | −0.051 (3) | 0.030 (3) | −0.027 (3) |
C24 | 0.073 (6) | 0.069 (4) | 0.047 (2) | 0.011 (4) | 0.007 (3) | −0.003 (3) |
C25 | 0.114 (13) | 0.084 (4) | 0.061 (2) | 0.035 (4) | 0.028 (3) | 0.003 (2) |
C26 | 0.155 (9) | 0.126 (8) | 0.081 (5) | 0.065 (7) | 0.034 (6) | −0.008 (4) |
C27 | 0.230 (10) | 0.192 (9) | 0.119 (7) | 0.085 (8) | 0.081 (8) | −0.032 (6) |
O4 | 0.156 (7) | 0.158 (7) | 0.063 (3) | 0.090 (6) | −0.003 (4) | −0.005 (3) |
O5 | 0.117 (6) | 0.088 (4) | 0.0712 (17) | 0.020 (4) | 0.042 (3) | −0.004 (3) |
C24A | 0.073 (6) | 0.069 (4) | 0.047 (2) | 0.011 (4) | 0.007 (3) | −0.003 (3) |
C25A | 0.114 (13) | 0.084 (4) | 0.061 (2) | 0.035 (4) | 0.028 (3) | 0.003 (2) |
C26A | 0.155 (9) | 0.126 (8) | 0.081 (5) | 0.065 (7) | 0.034 (6) | −0.008 (4) |
C27A | 0.230 (10) | 0.192 (9) | 0.119 (7) | 0.085 (8) | 0.081 (8) | −0.032 (6) |
O4A | 0.156 (7) | 0.158 (7) | 0.063 (3) | 0.090 (6) | −0.003 (4) | −0.005 (3) |
O5A | 0.117 (6) | 0.088 (4) | 0.0712 (17) | 0.020 (4) | 0.042 (3) | −0.004 (3) |
Br1 | 0.0766 (2) | 0.0737 (2) | 0.1095 (3) | 0.0167 (2) | 0.01751 (19) | −0.0036 (2) |
N1 | 0.0684 (15) | 0.0621 (15) | 0.0479 (12) | 0.0061 (13) | 0.0113 (12) | −0.0024 (11) |
O1 | 0.0881 (16) | 0.0931 (16) | 0.0612 (13) | 0.0074 (15) | 0.0313 (12) | −0.0061 (12) |
O2 | 0.0757 (15) | 0.1000 (17) | 0.0752 (14) | 0.0071 (13) | 0.0309 (12) | 0.0005 (13) |
O3 | 0.121 (2) | 0.0860 (16) | 0.0742 (14) | −0.0224 (15) | 0.0390 (14) | −0.0258 (13) |
C1—C2 | 1.363 (4) | C19—C20 | 1.524 (5) |
C1—C6 | 1.386 (4) | C19—H19A | 0.9700 |
C1—H1 | 0.9300 | C19—H19B | 0.9700 |
C2—C3 | 1.380 (4) | C20—C22 | 1.522 (5) |
C2—Br1 | 1.892 (3) | C20—C21 | 1.534 (4) |
C3—C4 | 1.368 (4) | C20—C23 | 1.544 (5) |
C3—H3 | 0.9300 | C21—H21A | 0.9700 |
C4—C5 | 1.376 (4) | C21—H21B | 0.9700 |
C4—H4 | 0.9300 | C22—H22A | 0.9600 |
C5—O1 | 1.369 (4) | C22—H22B | 0.9600 |
C5—C6 | 1.398 (4) | C22—H22C | 0.9600 |
C6—C7 | 1.531 (4) | C23—H23A | 0.9600 |
C7—C17 | 1.496 (4) | C23—H23B | 0.9600 |
C7—C8 | 1.501 (4) | C23—H23C | 0.9600 |
C7—H7 | 0.9800 | C24—N1 | 1.479 (15) |
C8—C13 | 1.355 (4) | C24—C25 | 1.498 (16) |
C8—C9 | 1.451 (4) | C24—H24A | 0.9700 |
C9—O3 | 1.229 (3) | C24—H24B | 0.9700 |
C9—C10 | 1.491 (4) | C25—O4 | 1.21 (2) |
C10—C11 | 1.518 (4) | C25—O5 | 1.322 (18) |
C10—H10A | 0.9700 | C26—C27 | 1.458 (18) |
C10—H10B | 0.9700 | C26—O5 | 1.476 (16) |
C11—C12 | 1.522 (4) | C26—H26A | 0.9700 |
C11—C14 | 1.536 (5) | C26—H26B | 0.9700 |
C11—C15 | 1.541 (4) | C27—H27A | 0.9600 |
C12—C13 | 1.505 (4) | C27—H27B | 0.9600 |
C12—H12A | 0.9700 | C27—H27C | 0.9600 |
C12—H12B | 0.9700 | C24A—N1 | 1.470 (7) |
C13—N1 | 1.395 (4) | C24A—C25A | 1.496 (7) |
C14—H14A | 0.9600 | C24A—H24C | 0.9700 |
C14—H14B | 0.9600 | C24A—H24D | 0.9700 |
C14—H14C | 0.9600 | C25A—O4A | 1.204 (14) |
C15—H15A | 0.9600 | C25A—O5A | 1.314 (9) |
C15—H15B | 0.9600 | C26A—O5A | 1.463 (7) |
C15—H15C | 0.9600 | C26A—C27A | 1.468 (10) |
C16—C17 | 1.357 (4) | C26A—H26D | 0.9700 |
C16—N1 | 1.394 (3) | C26A—H26E | 0.9700 |
C16—C21 | 1.499 (4) | C27A—H27D | 0.9600 |
C17—C18 | 1.452 (4) | C27A—H27E | 0.9600 |
C18—O2 | 1.233 (4) | C27A—H27F | 0.9600 |
C18—C19 | 1.489 (5) | O1—H1A | 0.83 (4) |
C2—C1—C6 | 121.0 (3) | C20—C19—H19B | 109.2 |
C2—C1—H1 | 119.5 | H19A—C19—H19B | 107.9 |
C6—C1—H1 | 119.5 | C22—C20—C19 | 111.0 (3) |
C1—C2—C3 | 120.6 (3) | C22—C20—C21 | 110.2 (3) |
C1—C2—Br1 | 120.0 (2) | C19—C20—C21 | 108.1 (3) |
C3—C2—Br1 | 119.4 (2) | C22—C20—C23 | 109.8 (3) |
C4—C3—C2 | 119.2 (3) | C19—C20—C23 | 108.9 (3) |
C4—C3—H3 | 120.4 | C21—C20—C23 | 108.8 (3) |
C2—C3—H3 | 120.4 | C16—C21—C20 | 113.3 (3) |
C3—C4—C5 | 120.8 (3) | C16—C21—H21A | 108.9 |
C3—C4—H4 | 119.6 | C20—C21—H21A | 108.9 |
C5—C4—H4 | 119.6 | C16—C21—H21B | 108.9 |
O1—C5—C4 | 118.2 (3) | C20—C21—H21B | 108.9 |
O1—C5—C6 | 121.5 (3) | H21A—C21—H21B | 107.7 |
C4—C5—C6 | 120.2 (3) | C20—C22—H22A | 109.5 |
C1—C6—C5 | 118.0 (3) | C20—C22—H22B | 109.5 |
C1—C6—C7 | 120.6 (2) | H22A—C22—H22B | 109.5 |
C5—C6—C7 | 121.2 (2) | C20—C22—H22C | 109.5 |
C17—C7—C8 | 110.1 (2) | H22A—C22—H22C | 109.5 |
C17—C7—C6 | 109.0 (2) | H22B—C22—H22C | 109.5 |
C8—C7—C6 | 112.0 (2) | C20—C23—H23A | 109.5 |
C17—C7—H7 | 108.6 | C20—C23—H23B | 109.5 |
C8—C7—H7 | 108.6 | H23A—C23—H23B | 109.5 |
C6—C7—H7 | 108.6 | C20—C23—H23C | 109.5 |
C13—C8—C9 | 121.5 (2) | H23A—C23—H23C | 109.5 |
C13—C8—C7 | 121.7 (3) | H23B—C23—H23C | 109.5 |
C9—C8—C7 | 116.8 (2) | N1—C24—C25 | 103 (2) |
O3—C9—C8 | 121.0 (3) | N1—C24—H24A | 111.2 |
O3—C9—C10 | 121.4 (3) | C25—C24—H24A | 111.2 |
C8—C9—C10 | 117.6 (3) | N1—C24—H24B | 111.2 |
C9—C10—C11 | 111.9 (3) | C25—C24—H24B | 111.3 |
C9—C10—H10A | 109.2 | H24A—C24—H24B | 109.2 |
C11—C10—H10A | 109.2 | O4—C25—O5 | 103 (4) |
C9—C10—H10B | 109.2 | O4—C25—C24 | 131 (6) |
C11—C10—H10B | 109.2 | O5—C25—C24 | 114 (3) |
H10A—C10—H10B | 107.9 | C27—C26—O5 | 110 (2) |
C10—C11—C12 | 109.0 (3) | C27—C26—H26A | 109.8 |
C10—C11—C14 | 109.5 (3) | O5—C26—H26A | 109.8 |
C12—C11—C14 | 110.2 (3) | C27—C26—H26B | 109.8 |
C10—C11—C15 | 109.6 (3) | O5—C26—H26B | 109.8 |
C12—C11—C15 | 109.4 (3) | H26A—C26—H26B | 108.2 |
C14—C11—C15 | 109.2 (3) | C26—C27—H27A | 109.5 |
C13—C12—C11 | 114.3 (2) | C26—C27—H27B | 109.5 |
C13—C12—H12A | 108.7 | H27A—C27—H27B | 109.5 |
C11—C12—H12A | 108.7 | C26—C27—H27C | 109.5 |
C13—C12—H12B | 108.7 | H27A—C27—H27C | 109.5 |
C11—C12—H12B | 108.7 | H27B—C27—H27C | 109.5 |
H12A—C12—H12B | 107.6 | C25—O5—C26 | 134 (3) |
C8—C13—N1 | 120.5 (2) | N1—C24A—C25A | 114.9 (8) |
C8—C13—C12 | 121.2 (3) | N1—C24A—H24C | 108.5 |
N1—C13—C12 | 118.3 (2) | C25A—C24A—H24C | 108.5 |
C11—C14—H14A | 109.5 | N1—C24A—H24D | 108.5 |
C11—C14—H14B | 109.5 | C25A—C24A—H24D | 108.5 |
H14A—C14—H14B | 109.5 | H24C—C24A—H24D | 107.5 |
C11—C14—H14C | 109.5 | O4A—C25A—O5A | 127.5 (16) |
H14A—C14—H14C | 109.5 | O4A—C25A—C24A | 121.6 (10) |
H14B—C14—H14C | 109.5 | O5A—C25A—C24A | 109.3 (7) |
C11—C15—H15A | 109.5 | O5A—C26A—C27A | 106.3 (8) |
C11—C15—H15B | 109.5 | O5A—C26A—H26D | 110.5 |
H15A—C15—H15B | 109.5 | C27A—C26A—H26D | 110.5 |
C11—C15—H15C | 109.5 | O5A—C26A—H26E | 110.5 |
H15A—C15—H15C | 109.5 | C27A—C26A—H26E | 110.5 |
H15B—C15—H15C | 109.5 | H26D—C26A—H26E | 108.7 |
C17—C16—N1 | 119.9 (3) | C26A—C27A—H27D | 109.5 |
C17—C16—C21 | 121.8 (3) | C26A—C27A—H27E | 109.5 |
N1—C16—C21 | 118.3 (2) | H27D—C27A—H27E | 109.5 |
C16—C17—C18 | 120.6 (3) | C26A—C27A—H27F | 109.5 |
C16—C17—C7 | 121.7 (2) | H27D—C27A—H27F | 109.5 |
C18—C17—C7 | 117.6 (2) | H27E—C27A—H27F | 109.5 |
O2—C18—C17 | 120.9 (3) | C25A—O5A—C26A | 112.0 (10) |
O2—C18—C19 | 121.0 (3) | C16—N1—C13 | 120.6 (2) |
C17—C18—C19 | 118.0 (3) | C16—N1—C24A | 121.0 (9) |
C18—C19—C20 | 112.0 (3) | C13—N1—C24A | 118.3 (10) |
C18—C19—H19A | 109.2 | C16—N1—C24 | 117 (2) |
C20—C19—H19A | 109.2 | C13—N1—C24 | 121 (3) |
C18—C19—H19B | 109.2 | C5—O1—H1A | 109 (3) |
C6—C1—C2—C3 | −0.1 (4) | C6—C7—C17—C16 | −96.9 (3) |
C6—C1—C2—Br1 | 178.7 (2) | C8—C7—C17—C18 | −156.6 (2) |
C1—C2—C3—C4 | 1.8 (4) | C6—C7—C17—C18 | 80.2 (3) |
Br1—C2—C3—C4 | −177.0 (2) | C16—C17—C18—O2 | −175.5 (3) |
C2—C3—C4—C5 | −1.0 (5) | C7—C17—C18—O2 | 7.3 (4) |
C3—C4—C5—O1 | 179.4 (3) | C16—C17—C18—C19 | 2.3 (4) |
C3—C4—C5—C6 | −1.5 (5) | C7—C17—C18—C19 | −174.8 (3) |
C2—C1—C6—C5 | −2.3 (4) | O2—C18—C19—C20 | −148.7 (3) |
C2—C1—C6—C7 | −177.5 (3) | C17—C18—C19—C20 | 33.4 (4) |
O1—C5—C6—C1 | −177.8 (3) | C18—C19—C20—C22 | 63.8 (4) |
C4—C5—C6—C1 | 3.1 (4) | C18—C19—C20—C21 | −57.2 (4) |
O1—C5—C6—C7 | −2.7 (4) | C18—C19—C20—C23 | −175.3 (3) |
C4—C5—C6—C7 | 178.2 (3) | C17—C16—C21—C20 | −15.0 (4) |
C1—C6—C7—C17 | 77.5 (3) | N1—C16—C21—C20 | 164.7 (3) |
C5—C6—C7—C17 | −97.5 (3) | C22—C20—C21—C16 | −73.3 (4) |
C1—C6—C7—C8 | −44.6 (4) | C19—C20—C21—C16 | 48.2 (4) |
C5—C6—C7—C8 | 140.4 (3) | C23—C20—C21—C16 | 166.3 (3) |
C17—C7—C8—C13 | −22.0 (4) | N1—C24—C25—O4 | 39 (12) |
C6—C7—C8—C13 | 99.3 (3) | N1—C24—C25—O5 | 174 (6) |
C17—C7—C8—C9 | 157.9 (3) | O4—C25—O5—C26 | −35 (11) |
C6—C7—C8—C9 | −80.7 (3) | C24—C25—O5—C26 | 177 (4) |
C13—C8—C9—O3 | −176.1 (3) | C27—C26—O5—C25 | −82 (7) |
C7—C8—C9—O3 | 4.0 (4) | N1—C24A—C25A—O4A | −4 (5) |
C13—C8—C9—C10 | 4.5 (4) | N1—C24A—C25A—O5A | −171.2 (18) |
C7—C8—C9—C10 | −175.5 (3) | O4A—C25A—O5A—C26A | 9 (4) |
O3—C9—C10—C11 | 143.5 (3) | C24A—C25A—O5A—C26A | 175 (2) |
C8—C9—C10—C11 | −37.1 (4) | C27A—C26A—O5A—C25A | −177 (2) |
C9—C10—C11—C12 | 56.5 (4) | C17—C16—N1—C13 | −4.2 (4) |
C9—C10—C11—C14 | −64.1 (4) | C21—C16—N1—C13 | 176.1 (3) |
C9—C10—C11—C15 | 176.1 (3) | C17—C16—N1—C24A | 178.7 (7) |
C10—C11—C12—C13 | −45.9 (4) | C21—C16—N1—C24A | −1.0 (8) |
C14—C11—C12—C13 | 74.2 (3) | C17—C16—N1—C24 | −170 (2) |
C15—C11—C12—C13 | −165.7 (3) | C21—C16—N1—C24 | 10 (2) |
C9—C8—C13—N1 | −173.6 (3) | C8—C13—N1—C16 | 8.4 (4) |
C7—C8—C13—N1 | 6.3 (4) | C12—C13—N1—C16 | −172.1 (2) |
C9—C8—C13—C12 | 6.9 (4) | C8—C13—N1—C24A | −174.4 (7) |
C7—C8—C13—C12 | −173.2 (3) | C12—C13—N1—C24A | 5.1 (7) |
C11—C12—C13—C8 | 15.2 (4) | C8—C13—N1—C24 | 174 (2) |
C11—C12—C13—N1 | −164.3 (3) | C12—C13—N1—C24 | −7 (2) |
N1—C16—C17—C18 | 168.4 (3) | C25A—C24A—N1—C16 | −97 (2) |
C21—C16—C17—C18 | −11.9 (4) | C25A—C24A—N1—C13 | 86 (3) |
N1—C16—C17—C7 | −14.6 (4) | C25—C24—N1—C16 | −102 (5) |
C21—C16—C17—C7 | 165.1 (3) | C25—C24—N1—C13 | 92 (6) |
C8—C7—C17—C16 | 26.3 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O2 | 0.83 (4) | 1.87 (4) | 2.674 (3) | 164 (4) |
C7—H7···O1 | 0.98 | 2.49 | 2.910 (3) | 105 |
C14—H14A···O1i | 0.96 | 2.53 | 3.438 (4) | 158 |
Symmetry code: (i) x+1/2, −y+3/2, z−1/2. |
Acknowledgements
The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).
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