organic compounds
1-(4-Methoxyphenyl)-3-[2-(4-methylpiperazin-1-yl)quinolin-3-yl]prop-2-en-1-one
aDepartment of Physics , University of Jammu, Jammu Tawi 180 006, India, bDepartment of Chemistry, Tumkur University Tumkur, India, and cDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur 572 103. Karnataka, India
*Correspondence e-mail: rkant.ju@gmail.com
In the title molecule, C24H25N3O2, the piperazine ring adopts a chair conformation. The methoxyphenyl-substituted ring makes a dihedral angle of 6.79 (5)° with the quinoline ring system. In the crystal, molecules are consolidated in the crystal packing by a combination of weak C—H⋯N and C—H⋯O interactions. π–π stacking interactions also occur.
CCDC reference: 1584069
Structure description
Quinoline derivatives find importance owing to their wide occurrence in natural products and in biologically active compounds (Markees et al., 1970; Campbell et al., 1988; Kalluraya & Sreenivasa, 1998). Quinoline chalcone analogues have also attracted significant attention as a result of their bio-activity, e.g. anti-plasmodial, anti-microbial, anti-malarial and anti-cancer (Dimmock et al., 1999; Wu et al., 2006).
In the molecule of the title compound, (Fig. 1), bond lengths are in normal ranges and are comparable with related structures (Kaiser et al., 2009; Prasath et al., 2010, 2011). The piperazine ring adopts a chair conformation with best mirror plane passing through atoms C20 and C22 [asymmetry parameter ΔCs(C20) = 2/3] and the best twofold rotational axis bisecting the C22—C23 and C20—C21 bonds [asymmetry parameter ΔC2(C22—C23) = 0.43; Duax & Norton, 1975). The quinoline ring system is essentially planar with a maximum deviation of 0.0384 (1) Å for atom C17. The methoxyphenyl-substituted ring makes a dihedral angle of 6.79 (5)° with the quinoline ring system.
In the crystal, molecules are consolidated in the crystal packing by a combination of weak C—H⋯N and C—H⋯O interactions (Table 1, Fig. 2). The also features π–π stacking interactions observed between the (C11–C13/C18/N1/C19) ring and the methoxyphenyl-substituted ring [centroid–centroid separation = 3.680 (1) Å, interplanar spacing = 3.350 Å and centroid shift = 1.52 Å] and the benzene ring (C13–C18) and the methoxyphenyl-substituted ring [centroid separation = 3.760 (1) Å, interplanar spacing = 3.625 Å and centroid shift = 1.00 Å].
Synthesis and crystallization
To a mixture of 9-acetylanthracene (0.01 mol) and 3-nitrobenzaldehyde (0.01 mol) in ethanol (50 ml), 15 ml of 10% sodium hydroxide solution was added and stirred at 273–278 K for 3 h. The precipitate formed was collected by filtration and purified by recrystallization from ethanol. Single crystals were grown from DMF by the slow evaporation method (m.p. 441–443 K).
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1584069
https://doi.org/10.1107/S2414314617016005/lh4028sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617016005/lh4028Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617016005/lh4028Isup3.cml
Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell
CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek,2009).C24H25N3O2 | F(000) = 824 |
Mr = 387.47 | Dx = 1.264 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.1054 (9) Å | Cell parameters from 2213 reflections |
b = 12.5816 (8) Å | θ = 3.8–28.1° |
c = 13.8151 (10) Å | µ = 0.08 mm−1 |
β = 104.660 (8)° | T = 293 K |
V = 2035.6 (3) Å3 | Block, white |
Z = 4 | 0.30 × 0.20 × 0.20 mm |
Oxford Diffraction Xcalibur, Sapphire3 diffractometer | 3968 independent reflections |
Radiation source: fine-focus sealed tube | 2661 reflections with I > 2σ(I) |
Detector resolution: 6.1049 pixels mm-1 | Rint = 0.029 |
ω scans | θmax = 26.0°, θmin = 3.7° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010) | h = −10→14 |
Tmin = 0.806, Tmax = 1.000 | k = −15→9 |
7663 measured reflections | l = −17→13 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.129 | w = 1/[σ2(Fo2) + (0.0522P)2 + 0.2064P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.002 |
3968 reflections | Δρmax = 0.14 e Å−3 |
264 parameters | Δρmin = −0.16 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. |
Refinement. All H atoms were positioned geometrically and were treated as riding on their parent C atoms, with C—H distances of 0.93–0.97 Å; and with Uiso(H) = 1.2Ueq(C), except for the methyl groups where Uiso(H) = 1.5Ueq(C). |
x | y | z | Uiso*/Ueq | ||
N1 | 0.66324 (12) | 0.04111 (11) | 0.17671 (11) | 0.0403 (4) | |
C19 | 0.68787 (15) | −0.02479 (13) | 0.11184 (13) | 0.0370 (4) | |
N2 | 0.65342 (12) | −0.13104 (11) | 0.11343 (10) | 0.0401 (4) | |
C13 | 0.75452 (15) | 0.18349 (13) | 0.10684 (13) | 0.0399 (4) | |
C18 | 0.69723 (14) | 0.14485 (13) | 0.17632 (13) | 0.0377 (4) | |
C11 | 0.75333 (15) | 0.00475 (13) | 0.04249 (13) | 0.0381 (4) | |
C5 | 0.94339 (15) | −0.12384 (14) | −0.21987 (13) | 0.0396 (4) | |
O1 | 1.11216 (12) | −0.07992 (10) | −0.44155 (10) | 0.0572 (4) | |
N3 | 0.52218 (13) | −0.31851 (11) | 0.11631 (12) | 0.0464 (4) | |
C10 | 0.79570 (15) | −0.07570 (14) | −0.01499 (14) | 0.0434 (5) | |
H10 | 0.786172 | −0.146122 | 0.001693 | 0.052* | |
O2 | 0.86919 (14) | −0.24023 (10) | −0.11961 (11) | 0.0661 (4) | |
C4 | 0.99289 (16) | −0.02680 (14) | −0.22924 (13) | 0.0430 (5) | |
H4 | 0.987250 | 0.027752 | −0.185317 | 0.052* | |
C17 | 0.67233 (16) | 0.21571 (14) | 0.24651 (14) | 0.0466 (5) | |
H17 | 0.636395 | 0.191100 | 0.294237 | 0.056* | |
C23 | 0.62185 (18) | −0.16514 (14) | 0.20369 (14) | 0.0511 (5) | |
H23A | 0.550435 | −0.131980 | 0.206621 | 0.061* | |
H23B | 0.680250 | −0.143472 | 0.262350 | 0.061* | |
C12 | 0.78272 (16) | 0.10930 (14) | 0.04139 (13) | 0.0431 (5) | |
H12 | 0.822651 | 0.131995 | −0.004154 | 0.052* | |
C16 | 0.70063 (17) | 0.32018 (14) | 0.24486 (15) | 0.0519 (5) | |
H16 | 0.682082 | 0.366850 | 0.290523 | 0.062* | |
C7 | 1.00681 (18) | −0.18600 (14) | −0.36065 (15) | 0.0527 (5) | |
H7 | 1.010137 | −0.239544 | −0.406238 | 0.063* | |
C8 | 0.88595 (16) | −0.14806 (15) | −0.14025 (14) | 0.0448 (5) | |
C2 | 1.05822 (16) | −0.08888 (14) | −0.36738 (14) | 0.0430 (5) | |
C14 | 0.78453 (17) | 0.29115 (14) | 0.10835 (15) | 0.0495 (5) | |
H14 | 0.823418 | 0.316742 | 0.063107 | 0.059* | |
C9 | 0.84587 (17) | −0.05991 (15) | −0.08776 (14) | 0.0492 (5) | |
H9 | 0.856454 | 0.009486 | −0.106793 | 0.059* | |
C22 | 0.60924 (18) | −0.28353 (15) | 0.20268 (15) | 0.0539 (5) | |
H22A | 0.681542 | −0.316235 | 0.201805 | 0.065* | |
H22B | 0.589184 | −0.306217 | 0.263146 | 0.065* | |
C21 | 0.55201 (18) | −0.28423 (14) | 0.02596 (15) | 0.0519 (5) | |
H21A | 0.492652 | −0.305925 | −0.032006 | 0.062* | |
H21B | 0.622716 | −0.318125 | 0.022020 | 0.062* | |
C20 | 0.56593 (17) | −0.16596 (14) | 0.02492 (14) | 0.0476 (5) | |
H20A | 0.587873 | −0.144925 | −0.035153 | 0.057* | |
H20B | 0.493794 | −0.131959 | 0.024143 | 0.057* | |
C3 | 1.05028 (16) | −0.00856 (14) | −0.30169 (14) | 0.0440 (5) | |
H3 | 1.083415 | 0.057313 | −0.306325 | 0.053* | |
C6 | 0.95132 (18) | −0.20370 (15) | −0.28761 (15) | 0.0514 (5) | |
H6 | 0.918482 | −0.269727 | −0.283015 | 0.062* | |
C15 | 0.75707 (17) | 0.35818 (15) | 0.17556 (16) | 0.0530 (5) | |
H15 | 0.775998 | 0.429808 | 0.175411 | 0.064* | |
C24 | 0.5069 (2) | −0.43288 (15) | 0.11815 (19) | 0.0685 (7) | |
H24A | 0.447997 | −0.454164 | 0.060792 | 0.103* | |
H24B | 0.485380 | −0.452479 | 0.178032 | 0.103* | |
H24C | 0.577077 | −0.467626 | 0.116856 | 0.103* | |
C1 | 1.17742 (19) | 0.01359 (15) | −0.44464 (16) | 0.0601 (6) | |
H1A | 1.128690 | 0.074776 | −0.451322 | 0.090* | |
H1B | 1.210611 | 0.009934 | −0.500733 | 0.090* | |
H1C | 1.236977 | 0.019112 | −0.383948 | 0.090* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0412 (9) | 0.0439 (8) | 0.0390 (9) | −0.0042 (7) | 0.0159 (7) | −0.0015 (7) |
C19 | 0.0351 (10) | 0.0426 (10) | 0.0330 (10) | −0.0027 (8) | 0.0082 (8) | 0.0027 (8) |
N2 | 0.0437 (9) | 0.0430 (8) | 0.0341 (9) | −0.0088 (7) | 0.0109 (7) | −0.0005 (7) |
C13 | 0.0382 (10) | 0.0431 (10) | 0.0401 (11) | −0.0010 (8) | 0.0131 (8) | 0.0041 (8) |
C18 | 0.0336 (9) | 0.0414 (10) | 0.0389 (10) | −0.0012 (8) | 0.0108 (8) | 0.0001 (8) |
C11 | 0.0387 (10) | 0.0437 (10) | 0.0329 (10) | −0.0014 (8) | 0.0112 (8) | 0.0020 (8) |
C5 | 0.0386 (10) | 0.0427 (10) | 0.0374 (10) | 0.0080 (8) | 0.0096 (8) | −0.0005 (8) |
O1 | 0.0688 (10) | 0.0589 (9) | 0.0542 (9) | −0.0094 (7) | 0.0349 (8) | −0.0149 (7) |
N3 | 0.0481 (9) | 0.0412 (9) | 0.0540 (10) | −0.0087 (7) | 0.0203 (8) | −0.0072 (7) |
C10 | 0.0441 (11) | 0.0459 (10) | 0.0423 (11) | −0.0020 (9) | 0.0145 (9) | −0.0002 (8) |
O2 | 0.0970 (12) | 0.0472 (8) | 0.0651 (10) | 0.0037 (8) | 0.0410 (9) | 0.0072 (7) |
C4 | 0.0430 (11) | 0.0469 (11) | 0.0406 (11) | 0.0040 (9) | 0.0130 (9) | −0.0099 (9) |
C17 | 0.0492 (12) | 0.0503 (11) | 0.0453 (12) | −0.0034 (9) | 0.0211 (9) | −0.0028 (9) |
C23 | 0.0645 (13) | 0.0529 (11) | 0.0379 (11) | −0.0167 (10) | 0.0166 (10) | −0.0015 (9) |
C12 | 0.0447 (11) | 0.0504 (11) | 0.0387 (11) | −0.0018 (9) | 0.0188 (9) | 0.0058 (9) |
C16 | 0.0524 (12) | 0.0487 (11) | 0.0575 (14) | −0.0018 (10) | 0.0193 (11) | −0.0114 (10) |
C7 | 0.0696 (14) | 0.0430 (11) | 0.0516 (13) | −0.0004 (10) | 0.0264 (11) | −0.0117 (9) |
C8 | 0.0485 (11) | 0.0462 (11) | 0.0403 (11) | 0.0068 (9) | 0.0123 (9) | 0.0023 (9) |
C2 | 0.0419 (11) | 0.0488 (11) | 0.0408 (11) | 0.0040 (9) | 0.0153 (9) | −0.0055 (9) |
C14 | 0.0533 (12) | 0.0453 (10) | 0.0551 (13) | −0.0043 (9) | 0.0230 (10) | 0.0056 (10) |
C9 | 0.0597 (13) | 0.0461 (11) | 0.0476 (12) | 0.0053 (10) | 0.0243 (10) | 0.0031 (9) |
C22 | 0.0593 (13) | 0.0537 (12) | 0.0494 (13) | −0.0102 (10) | 0.0149 (10) | 0.0073 (10) |
C21 | 0.0530 (12) | 0.0560 (12) | 0.0478 (12) | −0.0089 (10) | 0.0149 (10) | −0.0133 (10) |
C20 | 0.0492 (12) | 0.0545 (11) | 0.0382 (11) | −0.0078 (9) | 0.0091 (9) | −0.0005 (9) |
C3 | 0.0440 (11) | 0.0437 (10) | 0.0467 (12) | −0.0020 (9) | 0.0161 (9) | −0.0082 (9) |
C6 | 0.0646 (14) | 0.0415 (10) | 0.0534 (13) | 0.0009 (10) | 0.0246 (11) | −0.0033 (9) |
C15 | 0.0527 (12) | 0.0417 (11) | 0.0657 (14) | −0.0058 (9) | 0.0170 (11) | −0.0029 (10) |
C24 | 0.0784 (17) | 0.0465 (12) | 0.0893 (18) | −0.0112 (11) | 0.0370 (14) | −0.0112 (11) |
C1 | 0.0659 (15) | 0.0636 (13) | 0.0588 (14) | −0.0145 (11) | 0.0307 (12) | −0.0108 (11) |
N1—C19 | 1.309 (2) | C23—H23B | 0.9700 |
N1—C18 | 1.369 (2) | C12—H12 | 0.9300 |
C19—N2 | 1.402 (2) | C16—C15 | 1.394 (3) |
C19—C11 | 1.438 (2) | C16—H16 | 0.9300 |
N2—C23 | 1.458 (2) | C7—C6 | 1.365 (2) |
N2—C20 | 1.468 (2) | C7—C2 | 1.385 (2) |
C13—C14 | 1.401 (2) | C7—H7 | 0.9300 |
C13—C12 | 1.401 (2) | C8—C9 | 1.473 (2) |
C13—C18 | 1.406 (2) | C2—C3 | 1.378 (2) |
C18—C17 | 1.405 (2) | C14—C15 | 1.357 (3) |
C11—C12 | 1.364 (2) | C14—H14 | 0.9300 |
C11—C10 | 1.458 (2) | C9—H9 | 0.9300 |
C5—C4 | 1.381 (2) | C22—H22A | 0.9700 |
C5—C6 | 1.393 (2) | C22—H22B | 0.9700 |
C5—C8 | 1.474 (2) | C21—C20 | 1.498 (2) |
O1—C2 | 1.352 (2) | C21—H21A | 0.9700 |
O1—C1 | 1.424 (2) | C21—H21B | 0.9700 |
N3—C22 | 1.446 (2) | C20—H20A | 0.9700 |
N3—C21 | 1.450 (2) | C20—H20B | 0.9700 |
N3—C24 | 1.452 (2) | C3—H3 | 0.9300 |
C10—C9 | 1.315 (2) | C6—H6 | 0.9300 |
C10—H10 | 0.9300 | C15—H15 | 0.9300 |
O2—C8 | 1.223 (2) | C24—H24A | 0.9600 |
C4—C3 | 1.374 (2) | C24—H24B | 0.9600 |
C4—H4 | 0.9300 | C24—H24C | 0.9600 |
C17—C16 | 1.360 (2) | C1—H1A | 0.9600 |
C17—H17 | 0.9300 | C1—H1B | 0.9600 |
C23—C22 | 1.497 (2) | C1—H1C | 0.9600 |
C23—H23A | 0.9700 | ||
C19—N1—C18 | 118.71 (14) | C9—C8—C5 | 119.22 (16) |
N1—C19—N2 | 118.22 (15) | O1—C2—C3 | 124.44 (16) |
N1—C19—C11 | 123.47 (15) | O1—C2—C7 | 115.85 (16) |
N2—C19—C11 | 118.23 (15) | C3—C2—C7 | 119.70 (17) |
C19—N2—C23 | 115.93 (14) | C15—C14—C13 | 120.24 (17) |
C19—N2—C20 | 115.28 (14) | C15—C14—H14 | 119.9 |
C23—N2—C20 | 109.53 (14) | C13—C14—H14 | 119.9 |
C14—C13—C12 | 123.31 (16) | C10—C9—C8 | 122.43 (17) |
C14—C13—C18 | 119.68 (16) | C10—C9—H9 | 118.8 |
C12—C13—C18 | 116.96 (15) | C8—C9—H9 | 118.8 |
N1—C18—C13 | 122.23 (15) | N3—C22—C23 | 111.21 (16) |
N1—C18—C17 | 119.01 (15) | N3—C22—H22A | 109.4 |
C13—C18—C17 | 118.75 (15) | C23—C22—H22A | 109.4 |
C12—C11—C19 | 116.49 (15) | N3—C22—H22B | 109.4 |
C12—C11—C10 | 122.34 (15) | C23—C22—H22B | 109.4 |
C19—C11—C10 | 120.84 (15) | H22A—C22—H22B | 108.0 |
C4—C5—C6 | 118.01 (17) | N3—C21—C20 | 110.90 (15) |
C4—C5—C8 | 123.41 (16) | N3—C21—H21A | 109.5 |
C6—C5—C8 | 118.55 (16) | C20—C21—H21A | 109.5 |
C2—O1—C1 | 118.02 (14) | N3—C21—H21B | 109.5 |
C22—N3—C21 | 109.36 (15) | C20—C21—H21B | 109.5 |
C22—N3—C24 | 110.90 (16) | H21A—C21—H21B | 108.0 |
C21—N3—C24 | 111.75 (15) | N2—C20—C21 | 110.39 (15) |
C9—C10—C11 | 127.31 (17) | N2—C20—H20A | 109.6 |
C9—C10—H10 | 116.3 | C21—C20—H20A | 109.6 |
C11—C10—H10 | 116.3 | N2—C20—H20B | 109.6 |
C3—C4—C5 | 121.83 (16) | C21—C20—H20B | 109.6 |
C3—C4—H4 | 119.1 | H20A—C20—H20B | 108.1 |
C5—C4—H4 | 119.1 | C4—C3—C2 | 119.31 (17) |
C16—C17—C18 | 120.18 (17) | C4—C3—H3 | 120.3 |
C16—C17—H17 | 119.9 | C2—C3—H3 | 120.3 |
C18—C17—H17 | 119.9 | C7—C6—C5 | 120.64 (18) |
N2—C23—C22 | 109.45 (15) | C7—C6—H6 | 119.7 |
N2—C23—H23A | 109.8 | C5—C6—H6 | 119.7 |
C22—C23—H23A | 109.8 | C14—C15—C16 | 120.30 (17) |
N2—C23—H23B | 109.8 | C14—C15—H15 | 119.9 |
C22—C23—H23B | 109.8 | C16—C15—H15 | 119.9 |
H23A—C23—H23B | 108.2 | N3—C24—H24A | 109.5 |
C11—C12—C13 | 121.92 (16) | N3—C24—H24B | 109.5 |
C11—C12—H12 | 119.0 | H24A—C24—H24B | 109.5 |
C13—C12—H12 | 119.0 | N3—C24—H24C | 109.5 |
C17—C16—C15 | 120.82 (18) | H24A—C24—H24C | 109.5 |
C17—C16—H16 | 119.6 | H24B—C24—H24C | 109.5 |
C15—C16—H16 | 119.6 | O1—C1—H1A | 109.5 |
C6—C7—C2 | 120.48 (17) | O1—C1—H1B | 109.5 |
C6—C7—H7 | 119.8 | H1A—C1—H1B | 109.5 |
C2—C7—H7 | 119.8 | O1—C1—H1C | 109.5 |
O2—C8—C9 | 120.28 (17) | H1A—C1—H1C | 109.5 |
O2—C8—C5 | 120.48 (16) | H1B—C1—H1C | 109.5 |
C18—N1—C19—N2 | 179.50 (15) | C4—C5—C8—O2 | −161.56 (18) |
C18—N1—C19—C11 | 2.8 (3) | C6—C5—C8—O2 | 16.5 (3) |
N1—C19—N2—C23 | −16.4 (2) | C4—C5—C8—C9 | 20.2 (3) |
C11—C19—N2—C23 | 160.47 (16) | C6—C5—C8—C9 | −161.74 (18) |
N1—C19—N2—C20 | 113.40 (18) | C1—O1—C2—C3 | 8.3 (3) |
C11—C19—N2—C20 | −69.7 (2) | C1—O1—C2—C7 | −172.89 (18) |
C19—N1—C18—C13 | 1.9 (3) | C6—C7—C2—O1 | 179.19 (18) |
C19—N1—C18—C17 | −179.23 (16) | C6—C7—C2—C3 | −2.0 (3) |
C14—C13—C18—N1 | 178.29 (17) | C12—C13—C14—C15 | −178.26 (19) |
C12—C13—C18—N1 | −4.2 (3) | C18—C13—C14—C15 | −0.9 (3) |
C14—C13—C18—C17 | −0.5 (3) | C11—C10—C9—C8 | 179.61 (17) |
C12—C13—C18—C17 | 176.95 (17) | O2—C8—C9—C10 | 2.9 (3) |
N1—C19—C11—C12 | −4.9 (3) | C5—C8—C9—C10 | −178.87 (18) |
N2—C19—C11—C12 | 178.38 (15) | C21—N3—C22—C23 | 58.9 (2) |
N1—C19—C11—C10 | 168.70 (16) | C24—N3—C22—C23 | −177.45 (16) |
N2—C19—C11—C10 | −8.0 (3) | N2—C23—C22—N3 | −59.8 (2) |
C12—C11—C10—C9 | −14.4 (3) | C22—N3—C21—C20 | −57.6 (2) |
C19—C11—C10—C9 | 172.4 (2) | C24—N3—C21—C20 | 179.26 (17) |
C6—C5—C4—C3 | −1.1 (3) | C19—N2—C20—C21 | 169.36 (14) |
C8—C5—C4—C3 | 176.98 (17) | C23—N2—C20—C21 | −57.75 (19) |
N1—C18—C17—C16 | −177.06 (17) | N3—C21—C20—N2 | 57.7 (2) |
C13—C18—C17—C16 | 1.8 (3) | C5—C4—C3—C2 | 0.4 (3) |
C19—N2—C23—C22 | −169.17 (16) | O1—C2—C3—C4 | 179.83 (18) |
C20—N2—C23—C22 | 58.3 (2) | C7—C2—C3—C4 | 1.1 (3) |
C19—C11—C12—C13 | 2.3 (3) | C2—C7—C6—C5 | 1.3 (3) |
C10—C11—C12—C13 | −171.15 (17) | C4—C5—C6—C7 | 0.2 (3) |
C14—C13—C12—C11 | 179.28 (18) | C8—C5—C6—C7 | −177.96 (18) |
C18—C13—C12—C11 | 1.9 (3) | C13—C14—C15—C16 | 1.2 (3) |
C18—C17—C16—C15 | −1.6 (3) | C17—C16—C15—C14 | 0.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···O2i | 0.96 | 2.52 | 3.3096 (2) | 139 |
C14—H14···O1i | 0.93 | 2.40 | 3.3112 (2) | 165 |
C17—H17···N3ii | 0.93 | 2.54 | 3.4029 (3) | 155 |
Symmetry codes: (i) −x+2, y+1/2, −z−1/2; (ii) −x+1, y+1/2, −z+1/2. |
Acknowledgements
RK acknowledges the Department of Science & Technology for a single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.
Funding information
Funding for this research was provided by: Indian Council of Medical Research (grant No. BIC/12(14)/2012 to Rajni Kant); Department of Science and Technology, Ministry of Science and Technology, Science and Engineering Research Board (grant No. EMR/2014/000467 to Rajni Kant).
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