organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2414-3146

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

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 27 March 2017; accepted 15 April 2017; online 28 April 2017)

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.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Acridine derivatives have been used as anti-malarial (Santelli-Rouvier et al., 2004[Santelli-Rouvier, C., Pradines, B., Berthelot, M., Parzy, D. & Barbe, J. (2004). Eur. J. Med. Chem. 39, 735-744.]) anti-bacterial (Wainwright, 2001[Wainwright, M. J. (2001). J. Antimicrob. Chemother. 47, 1-13.]), anti-leishmanial (Delmas et al., 2004[Delmas, F., Avellaneda, A., Di Giorgio, C., Robin, M., De Clercq, E., Timon-David, P. & Galy, J. P. (2004). Eur. J. Med. Chem. 39, 685-690.]) and anti-HIV (Hamy et al., 1998[Hamy, F., Brondani, V., Flörsheimer, A., Stark, W., Blommers, M. J. J. & Klimkait, T. (1998). Biochemistry, 37, 5086-5095.]) agents. They also have exhibited excellent results in chemotherapy of cancer (Cholody et al., 1996[Cholody, W., Horowska, B., Paradziej-Lukowicz, J., Martelli, S. & Konopa, J. (1996). J. Med. Chem. 39, 1028-1032.]; Rewcastle et al., 1986[Rewcastle, G., Atwell, G. J., Chambers, D., Baguley, B. C. & Denny, W. A. (1986). J. Med. Chem. 29, 472-477.]). As part of our studies in this area, we report herein the synthesis and crystal structure of the title compound (Fig. 1[link]).

[Figure 1]
Figure 1
View of the title compound, with displacement ellipsoids for non-H atoms drawn at the 20% probability level. The minor component is not shown for clarity.

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[Akkurt, M., Jasinski, J. P., Mohamed, S. K., Allah, O. A. A., Tamam, A. H. A. & Albayati, M. R. (2015). Acta Cryst. E71, o963-o964.]).

In the crystal, adjacent mol­ecules are connected by C—H⋯O inter­actions, forming C(12) chains along the c-axis direction (Table 1[link], Fig. 2[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1A⋯O2 0.83 (4) 1.87 (4) 2.674 (3) 164 (4)
C14—H14A⋯O1i 0.96 2.53 3.438 (4) 158
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].
[Figure 2]
Figure 2
A view along the a axis of the hydrogen bonding and crystal packing of the title compound. The minor component of the disorder is not shown for clarity.

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 refinement details are summarized in Table 2[link]. 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).

Table 2
Experimental details

Crystal data
Chemical formula C27H32BrNO5
Mr 530.44
Crystal system, space group Monoclinic, P21/n
Temperature (K) 296
a, b, c (Å) 10.1174 (5), 19.0567 (8), 14.0387 (7)
β (°) 105.254 (4)
V3) 2611.4 (2)
Z 4
Radiation type Mo Kα
μ (mm−1) 1.61
Crystal size (mm) 0.67 × 0.51 × 0.38
 
Data collection
Diffractometer Stoe IPDS 2
Absorption correction Integration (X-RED32; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.])
Tmin, Tmax 0.425, 0.620
No. of measured, independent and observed [I > 2σ(I)] reflections 15096, 5086, 3086
Rint 0.058
(sin θ/λ)max−1) 0.616
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.105, 0.97
No. of reflections 5086
No. of parameters 335
No. of restraints 8
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.21, −0.27
Computer programs: X-AREA and X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2016 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), ORTEP-3 for Windows and WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Structural data


Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: 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).

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 top
Crystal data top
C27H32BrNO5F(000) = 1104
Mr = 530.44Dx = 1.349 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.1174 (5) ÅCell parameters from 14005 reflections
b = 19.0567 (8) Åθ = 1.5–26.5°
c = 14.0387 (7) ŵ = 1.61 mm1
β = 105.254 (4)°T = 296 K
V = 2611.4 (2) Å3Prism, light yellow
Z = 40.67 × 0.51 × 0.38 mm
Data collection top
Stoe IPDS 2
diffractometer
5086 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus3086 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.058
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 1.9°
rotation method scansh = 1212
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 2123
Tmin = 0.425, Tmax = 0.620l = 1717
15096 measured reflections
Refinement top
Refinement on F28 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.045H 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 reflectionsΔρmax = 0.21 e Å3
335 parametersΔρmin = 0.27 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.6851 (3)0.67758 (15)0.4523 (2)0.0586 (7)
H10.68990.67670.38700.070*
C20.7688 (3)0.63487 (16)0.5199 (2)0.0633 (7)
C30.7638 (3)0.63521 (17)0.6172 (2)0.0709 (8)
H30.82290.60700.66350.085*
C40.6711 (3)0.67753 (18)0.6447 (2)0.0691 (8)
H40.66630.67740.71000.083*
C50.5848 (3)0.72029 (16)0.5770 (2)0.0624 (7)
C60.5930 (3)0.72224 (15)0.47920 (19)0.0556 (7)
C70.4953 (3)0.76780 (15)0.40186 (19)0.0576 (7)
H70.45750.80440.43610.069*
C80.5669 (3)0.80239 (15)0.33324 (19)0.0573 (7)
C90.6446 (3)0.86548 (16)0.3689 (2)0.0678 (8)
C100.7075 (4)0.90358 (18)0.2990 (3)0.0831 (10)
H10A0.78260.93230.33620.100*
H10B0.63980.93450.25800.100*
C110.7607 (3)0.85355 (17)0.2335 (2)0.0711 (8)
C120.6438 (3)0.80649 (17)0.17857 (19)0.0651 (8)
H12A0.58410.83340.12580.078*
H12B0.68170.76820.14850.078*
C130.5594 (3)0.77610 (15)0.24226 (19)0.0579 (7)
C140.8774 (4)0.8090 (2)0.2974 (2)0.0864 (10)
H14A0.91240.77820.25580.130*
H14B0.84320.78190.34340.130*
H14C0.94940.83930.33290.130*
C150.8154 (4)0.8958 (2)0.1583 (3)0.0936 (11)
H15A0.85040.86410.11770.140*
H15B0.88740.92640.19290.140*
H15C0.74240.92310.11760.140*
C160.3809 (3)0.69497 (15)0.2560 (2)0.0597 (7)
C170.3801 (3)0.72313 (15)0.3446 (2)0.0599 (7)
C180.2692 (3)0.70791 (17)0.3893 (2)0.0681 (8)
C190.1600 (4)0.6585 (2)0.3369 (3)0.0856 (10)
H19A0.08940.68460.29020.103*
H19B0.11840.63690.38450.103*
C200.2158 (4)0.6014 (2)0.2822 (3)0.0835 (10)
C210.2848 (3)0.63714 (17)0.2098 (2)0.0748 (9)
H21A0.33520.60220.18340.090*
H21B0.21450.65620.15510.090*
C220.3184 (5)0.55518 (19)0.3538 (3)0.1046 (12)
H22A0.35100.51930.31780.157*
H22B0.27460.53390.39960.157*
H22C0.39410.58320.38940.157*
C230.0952 (5)0.5564 (3)0.2230 (3)0.1238 (16)
H23A0.03370.58530.17510.186*
H23B0.04730.53650.26710.186*
H23C0.12970.51940.18970.186*
C240.454 (5)0.695 (3)0.1031 (19)0.065 (2)0.281 (11)
H24A0.46730.73230.06010.078*0.281 (11)
H24B0.36280.67490.07710.078*0.281 (11)
C250.562 (10)0.639 (3)0.114 (2)0.085 (4)0.281 (11)
C260.641 (2)0.5489 (14)0.004 (2)0.120 (4)0.281 (11)
H26A0.66980.51600.05850.144*0.281 (11)
H26B0.58720.52350.05270.144*0.281 (11)
C270.760 (3)0.5801 (14)0.019 (2)0.174 (4)0.281 (11)
H27A0.80910.60830.03620.261*0.281 (11)
H27B0.73160.60890.07630.261*0.281 (11)
H27C0.81950.54360.03040.261*0.281 (11)
O40.604 (2)0.5960 (14)0.1773 (15)0.132 (3)0.281 (11)
O50.556 (3)0.6046 (13)0.032 (2)0.089 (2)0.281 (11)
C24A0.4786 (15)0.6889 (11)0.1105 (7)0.065 (2)0.719 (11)
H24C0.49380.72640.06790.078*0.719 (11)
H24D0.39010.66830.07970.078*0.719 (11)
C25A0.587 (3)0.6342 (13)0.1170 (7)0.085 (4)0.719 (11)
C26A0.7064 (12)0.5693 (6)0.0292 (6)0.120 (4)0.719 (11)
H26D0.69160.52510.05900.144*0.719 (11)
H26E0.79300.58890.06670.144*0.719 (11)
C27A0.7075 (12)0.5587 (6)0.0742 (7)0.174 (4)0.719 (11)
H27D0.63130.52980.10660.261*0.719 (11)
H27E0.79140.53620.07670.261*0.719 (11)
H27F0.70050.60330.10700.261*0.719 (11)
O4A0.6676 (9)0.6200 (5)0.1941 (5)0.132 (3)0.719 (11)
O5A0.5942 (10)0.6180 (4)0.0276 (8)0.089 (2)0.719 (11)
Br10.89080 (4)0.57315 (2)0.48022 (3)0.08792 (16)
N10.4734 (2)0.71957 (12)0.20561 (15)0.0603 (6)
O10.4932 (2)0.76108 (14)0.60854 (15)0.0786 (7)
H1A0.420 (4)0.762 (2)0.565 (3)0.118*
O20.2634 (2)0.73668 (13)0.46674 (17)0.0816 (6)
O30.6568 (3)0.88686 (13)0.45337 (17)0.0911 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0626 (18)0.0575 (17)0.0548 (15)0.0010 (15)0.0141 (14)0.0010 (14)
C20.0578 (18)0.0571 (18)0.0705 (19)0.0048 (15)0.0087 (15)0.0001 (15)
C30.067 (2)0.067 (2)0.068 (2)0.0044 (17)0.0001 (16)0.0139 (16)
C40.073 (2)0.080 (2)0.0511 (16)0.0107 (18)0.0110 (16)0.0057 (16)
C50.0654 (19)0.0663 (18)0.0564 (17)0.0062 (16)0.0179 (15)0.0036 (15)
C60.0579 (17)0.0582 (17)0.0498 (15)0.0010 (14)0.0124 (13)0.0000 (13)
C70.0654 (18)0.0585 (17)0.0518 (15)0.0095 (15)0.0203 (14)0.0009 (13)
C80.0649 (18)0.0553 (17)0.0521 (15)0.0086 (14)0.0158 (14)0.0039 (13)
C90.077 (2)0.0612 (19)0.0700 (19)0.0064 (16)0.0273 (17)0.0022 (15)
C100.100 (3)0.067 (2)0.093 (2)0.0124 (19)0.044 (2)0.0077 (18)
C110.079 (2)0.0732 (19)0.0671 (18)0.0019 (18)0.0300 (18)0.0015 (16)
C120.073 (2)0.0708 (19)0.0525 (16)0.0077 (16)0.0182 (15)0.0091 (14)
C130.0614 (17)0.0580 (17)0.0531 (16)0.0110 (15)0.0129 (13)0.0073 (13)
C140.071 (2)0.116 (3)0.073 (2)0.008 (2)0.0203 (18)0.004 (2)
C150.108 (3)0.093 (3)0.093 (2)0.006 (2)0.050 (2)0.009 (2)
C160.0594 (18)0.0567 (17)0.0592 (17)0.0073 (14)0.0086 (15)0.0047 (14)
C170.0608 (18)0.0624 (18)0.0549 (16)0.0063 (15)0.0127 (14)0.0052 (14)
C180.0604 (19)0.070 (2)0.071 (2)0.0071 (16)0.0129 (16)0.0098 (16)
C190.070 (2)0.099 (3)0.086 (2)0.004 (2)0.0196 (19)0.010 (2)
C200.082 (2)0.077 (2)0.087 (2)0.018 (2)0.015 (2)0.0003 (19)
C210.077 (2)0.069 (2)0.0719 (19)0.0017 (18)0.0086 (17)0.0008 (16)
C220.125 (3)0.075 (3)0.110 (3)0.000 (2)0.025 (3)0.018 (2)
C230.116 (3)0.120 (4)0.134 (4)0.051 (3)0.030 (3)0.027 (3)
C240.073 (6)0.069 (4)0.047 (2)0.011 (4)0.007 (3)0.003 (3)
C250.114 (13)0.084 (4)0.061 (2)0.035 (4)0.028 (3)0.003 (2)
C260.155 (9)0.126 (8)0.081 (5)0.065 (7)0.034 (6)0.008 (4)
C270.230 (10)0.192 (9)0.119 (7)0.085 (8)0.081 (8)0.032 (6)
O40.156 (7)0.158 (7)0.063 (3)0.090 (6)0.003 (4)0.005 (3)
O50.117 (6)0.088 (4)0.0712 (17)0.020 (4)0.042 (3)0.004 (3)
C24A0.073 (6)0.069 (4)0.047 (2)0.011 (4)0.007 (3)0.003 (3)
C25A0.114 (13)0.084 (4)0.061 (2)0.035 (4)0.028 (3)0.003 (2)
C26A0.155 (9)0.126 (8)0.081 (5)0.065 (7)0.034 (6)0.008 (4)
C27A0.230 (10)0.192 (9)0.119 (7)0.085 (8)0.081 (8)0.032 (6)
O4A0.156 (7)0.158 (7)0.063 (3)0.090 (6)0.003 (4)0.005 (3)
O5A0.117 (6)0.088 (4)0.0712 (17)0.020 (4)0.042 (3)0.004 (3)
Br10.0766 (2)0.0737 (2)0.1095 (3)0.0167 (2)0.01751 (19)0.0036 (2)
N10.0684 (15)0.0621 (15)0.0479 (12)0.0061 (13)0.0113 (12)0.0024 (11)
O10.0881 (16)0.0931 (16)0.0612 (13)0.0074 (15)0.0313 (12)0.0061 (12)
O20.0757 (15)0.1000 (17)0.0752 (14)0.0071 (13)0.0309 (12)0.0005 (13)
O30.121 (2)0.0860 (16)0.0742 (14)0.0224 (15)0.0390 (14)0.0258 (13)
Geometric parameters (Å, º) top
C1—C21.363 (4)C19—C201.524 (5)
C1—C61.386 (4)C19—H19A0.9700
C1—H10.9300C19—H19B0.9700
C2—C31.380 (4)C20—C221.522 (5)
C2—Br11.892 (3)C20—C211.534 (4)
C3—C41.368 (4)C20—C231.544 (5)
C3—H30.9300C21—H21A0.9700
C4—C51.376 (4)C21—H21B0.9700
C4—H40.9300C22—H22A0.9600
C5—O11.369 (4)C22—H22B0.9600
C5—C61.398 (4)C22—H22C0.9600
C6—C71.531 (4)C23—H23A0.9600
C7—C171.496 (4)C23—H23B0.9600
C7—C81.501 (4)C23—H23C0.9600
C7—H70.9800C24—N11.479 (15)
C8—C131.355 (4)C24—C251.498 (16)
C8—C91.451 (4)C24—H24A0.9700
C9—O31.229 (3)C24—H24B0.9700
C9—C101.491 (4)C25—O41.21 (2)
C10—C111.518 (4)C25—O51.322 (18)
C10—H10A0.9700C26—C271.458 (18)
C10—H10B0.9700C26—O51.476 (16)
C11—C121.522 (4)C26—H26A0.9700
C11—C141.536 (5)C26—H26B0.9700
C11—C151.541 (4)C27—H27A0.9600
C12—C131.505 (4)C27—H27B0.9600
C12—H12A0.9700C27—H27C0.9600
C12—H12B0.9700C24A—N11.470 (7)
C13—N11.395 (4)C24A—C25A1.496 (7)
C14—H14A0.9600C24A—H24C0.9700
C14—H14B0.9600C24A—H24D0.9700
C14—H14C0.9600C25A—O4A1.204 (14)
C15—H15A0.9600C25A—O5A1.314 (9)
C15—H15B0.9600C26A—O5A1.463 (7)
C15—H15C0.9600C26A—C27A1.468 (10)
C16—C171.357 (4)C26A—H26D0.9700
C16—N11.394 (3)C26A—H26E0.9700
C16—C211.499 (4)C27A—H27D0.9600
C17—C181.452 (4)C27A—H27E0.9600
C18—O21.233 (4)C27A—H27F0.9600
C18—C191.489 (5)O1—H1A0.83 (4)
C2—C1—C6121.0 (3)C20—C19—H19B109.2
C2—C1—H1119.5H19A—C19—H19B107.9
C6—C1—H1119.5C22—C20—C19111.0 (3)
C1—C2—C3120.6 (3)C22—C20—C21110.2 (3)
C1—C2—Br1120.0 (2)C19—C20—C21108.1 (3)
C3—C2—Br1119.4 (2)C22—C20—C23109.8 (3)
C4—C3—C2119.2 (3)C19—C20—C23108.9 (3)
C4—C3—H3120.4C21—C20—C23108.8 (3)
C2—C3—H3120.4C16—C21—C20113.3 (3)
C3—C4—C5120.8 (3)C16—C21—H21A108.9
C3—C4—H4119.6C20—C21—H21A108.9
C5—C4—H4119.6C16—C21—H21B108.9
O1—C5—C4118.2 (3)C20—C21—H21B108.9
O1—C5—C6121.5 (3)H21A—C21—H21B107.7
C4—C5—C6120.2 (3)C20—C22—H22A109.5
C1—C6—C5118.0 (3)C20—C22—H22B109.5
C1—C6—C7120.6 (2)H22A—C22—H22B109.5
C5—C6—C7121.2 (2)C20—C22—H22C109.5
C17—C7—C8110.1 (2)H22A—C22—H22C109.5
C17—C7—C6109.0 (2)H22B—C22—H22C109.5
C8—C7—C6112.0 (2)C20—C23—H23A109.5
C17—C7—H7108.6C20—C23—H23B109.5
C8—C7—H7108.6H23A—C23—H23B109.5
C6—C7—H7108.6C20—C23—H23C109.5
C13—C8—C9121.5 (2)H23A—C23—H23C109.5
C13—C8—C7121.7 (3)H23B—C23—H23C109.5
C9—C8—C7116.8 (2)N1—C24—C25103 (2)
O3—C9—C8121.0 (3)N1—C24—H24A111.2
O3—C9—C10121.4 (3)C25—C24—H24A111.2
C8—C9—C10117.6 (3)N1—C24—H24B111.2
C9—C10—C11111.9 (3)C25—C24—H24B111.3
C9—C10—H10A109.2H24A—C24—H24B109.2
C11—C10—H10A109.2O4—C25—O5103 (4)
C9—C10—H10B109.2O4—C25—C24131 (6)
C11—C10—H10B109.2O5—C25—C24114 (3)
H10A—C10—H10B107.9C27—C26—O5110 (2)
C10—C11—C12109.0 (3)C27—C26—H26A109.8
C10—C11—C14109.5 (3)O5—C26—H26A109.8
C12—C11—C14110.2 (3)C27—C26—H26B109.8
C10—C11—C15109.6 (3)O5—C26—H26B109.8
C12—C11—C15109.4 (3)H26A—C26—H26B108.2
C14—C11—C15109.2 (3)C26—C27—H27A109.5
C13—C12—C11114.3 (2)C26—C27—H27B109.5
C13—C12—H12A108.7H27A—C27—H27B109.5
C11—C12—H12A108.7C26—C27—H27C109.5
C13—C12—H12B108.7H27A—C27—H27C109.5
C11—C12—H12B108.7H27B—C27—H27C109.5
H12A—C12—H12B107.6C25—O5—C26134 (3)
C8—C13—N1120.5 (2)N1—C24A—C25A114.9 (8)
C8—C13—C12121.2 (3)N1—C24A—H24C108.5
N1—C13—C12118.3 (2)C25A—C24A—H24C108.5
C11—C14—H14A109.5N1—C24A—H24D108.5
C11—C14—H14B109.5C25A—C24A—H24D108.5
H14A—C14—H14B109.5H24C—C24A—H24D107.5
C11—C14—H14C109.5O4A—C25A—O5A127.5 (16)
H14A—C14—H14C109.5O4A—C25A—C24A121.6 (10)
H14B—C14—H14C109.5O5A—C25A—C24A109.3 (7)
C11—C15—H15A109.5O5A—C26A—C27A106.3 (8)
C11—C15—H15B109.5O5A—C26A—H26D110.5
H15A—C15—H15B109.5C27A—C26A—H26D110.5
C11—C15—H15C109.5O5A—C26A—H26E110.5
H15A—C15—H15C109.5C27A—C26A—H26E110.5
H15B—C15—H15C109.5H26D—C26A—H26E108.7
C17—C16—N1119.9 (3)C26A—C27A—H27D109.5
C17—C16—C21121.8 (3)C26A—C27A—H27E109.5
N1—C16—C21118.3 (2)H27D—C27A—H27E109.5
C16—C17—C18120.6 (3)C26A—C27A—H27F109.5
C16—C17—C7121.7 (2)H27D—C27A—H27F109.5
C18—C17—C7117.6 (2)H27E—C27A—H27F109.5
O2—C18—C17120.9 (3)C25A—O5A—C26A112.0 (10)
O2—C18—C19121.0 (3)C16—N1—C13120.6 (2)
C17—C18—C19118.0 (3)C16—N1—C24A121.0 (9)
C18—C19—C20112.0 (3)C13—N1—C24A118.3 (10)
C18—C19—H19A109.2C16—N1—C24117 (2)
C20—C19—H19A109.2C13—N1—C24121 (3)
C18—C19—H19B109.2C5—O1—H1A109 (3)
C6—C1—C2—C30.1 (4)C6—C7—C17—C1696.9 (3)
C6—C1—C2—Br1178.7 (2)C8—C7—C17—C18156.6 (2)
C1—C2—C3—C41.8 (4)C6—C7—C17—C1880.2 (3)
Br1—C2—C3—C4177.0 (2)C16—C17—C18—O2175.5 (3)
C2—C3—C4—C51.0 (5)C7—C17—C18—O27.3 (4)
C3—C4—C5—O1179.4 (3)C16—C17—C18—C192.3 (4)
C3—C4—C5—C61.5 (5)C7—C17—C18—C19174.8 (3)
C2—C1—C6—C52.3 (4)O2—C18—C19—C20148.7 (3)
C2—C1—C6—C7177.5 (3)C17—C18—C19—C2033.4 (4)
O1—C5—C6—C1177.8 (3)C18—C19—C20—C2263.8 (4)
C4—C5—C6—C13.1 (4)C18—C19—C20—C2157.2 (4)
O1—C5—C6—C72.7 (4)C18—C19—C20—C23175.3 (3)
C4—C5—C6—C7178.2 (3)C17—C16—C21—C2015.0 (4)
C1—C6—C7—C1777.5 (3)N1—C16—C21—C20164.7 (3)
C5—C6—C7—C1797.5 (3)C22—C20—C21—C1673.3 (4)
C1—C6—C7—C844.6 (4)C19—C20—C21—C1648.2 (4)
C5—C6—C7—C8140.4 (3)C23—C20—C21—C16166.3 (3)
C17—C7—C8—C1322.0 (4)N1—C24—C25—O439 (12)
C6—C7—C8—C1399.3 (3)N1—C24—C25—O5174 (6)
C17—C7—C8—C9157.9 (3)O4—C25—O5—C2635 (11)
C6—C7—C8—C980.7 (3)C24—C25—O5—C26177 (4)
C13—C8—C9—O3176.1 (3)C27—C26—O5—C2582 (7)
C7—C8—C9—O34.0 (4)N1—C24A—C25A—O4A4 (5)
C13—C8—C9—C104.5 (4)N1—C24A—C25A—O5A171.2 (18)
C7—C8—C9—C10175.5 (3)O4A—C25A—O5A—C26A9 (4)
O3—C9—C10—C11143.5 (3)C24A—C25A—O5A—C26A175 (2)
C8—C9—C10—C1137.1 (4)C27A—C26A—O5A—C25A177 (2)
C9—C10—C11—C1256.5 (4)C17—C16—N1—C134.2 (4)
C9—C10—C11—C1464.1 (4)C21—C16—N1—C13176.1 (3)
C9—C10—C11—C15176.1 (3)C17—C16—N1—C24A178.7 (7)
C10—C11—C12—C1345.9 (4)C21—C16—N1—C24A1.0 (8)
C14—C11—C12—C1374.2 (3)C17—C16—N1—C24170 (2)
C15—C11—C12—C13165.7 (3)C21—C16—N1—C2410 (2)
C9—C8—C13—N1173.6 (3)C8—C13—N1—C168.4 (4)
C7—C8—C13—N16.3 (4)C12—C13—N1—C16172.1 (2)
C9—C8—C13—C126.9 (4)C8—C13—N1—C24A174.4 (7)
C7—C8—C13—C12173.2 (3)C12—C13—N1—C24A5.1 (7)
C11—C12—C13—C815.2 (4)C8—C13—N1—C24174 (2)
C11—C12—C13—N1164.3 (3)C12—C13—N1—C247 (2)
N1—C16—C17—C18168.4 (3)C25A—C24A—N1—C1697 (2)
C21—C16—C17—C1811.9 (4)C25A—C24A—N1—C1386 (3)
N1—C16—C17—C714.6 (4)C25—C24—N1—C16102 (5)
C21—C16—C17—C7165.1 (3)C25—C24—N1—C1392 (6)
C8—C7—C17—C1626.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O20.83 (4)1.87 (4)2.674 (3)164 (4)
C7—H7···O10.982.492.910 (3)105
C14—H14A···O1i0.962.533.438 (4)158
Symmetry code: (i) x+1/2, y+3/2, z1/2.
 

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).

References

First citationAkkurt, M., Jasinski, J. P., Mohamed, S. K., Allah, O. A. A., Tamam, A. H. A. & Albayati, M. R. (2015). Acta Cryst. E71, o963–o964.  CrossRef IUCr Journals Google Scholar
First citationCholody, W., Horowska, B., Paradziej-Lukowicz, J., Martelli, S. & Konopa, J. (1996). J. Med. Chem. 39, 1028–1032.  CrossRef CAS PubMed Google Scholar
First citationDelmas, F., Avellaneda, A., Di Giorgio, C., Robin, M., De Clercq, E., Timon-David, P. & Galy, J. P. (2004). Eur. J. Med. Chem. 39, 685–690.  CrossRef PubMed CAS Google Scholar
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationHamy, F., Brondani, V., Flörsheimer, A., Stark, W., Blommers, M. J. J. & Klimkait, T. (1998). Biochemistry, 37, 5086–5095.  CrossRef CAS PubMed Google Scholar
First citationRewcastle, G., Atwell, G. J., Chambers, D., Baguley, B. C. & Denny, W. A. (1986). J. Med. Chem. 29, 472–477.  CrossRef CAS PubMed Google Scholar
First citationSantelli-Rouvier, C., Pradines, B., Berthelot, M., Parzy, D. & Barbe, J. (2004). Eur. J. Med. Chem. 39, 735–744.  PubMed CAS Google Scholar
First citationSheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationStoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.  Google Scholar
First citationWainwright, M. J. (2001). J. Antimicrob. Chemother. 47, 1–13.  Web of Science CrossRef PubMed CAS Google Scholar

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