organic compounds
Diethyl 2,6-dimethyl-4-[4-(3-phenylacryloyloxy)phenyl]-1,4-dihydropyridine-3,5-dicarboxylate hemihydrate
aDepartment of Physics, Presidency College, Chennai 600 005, India, and bAsthagiri Herbal Research Foundation, Perungudi, Chennai 600 096, India
*Correspondence e-mail: aravindhanpresidency@gmail.com
In the title ester derivative, C28H29NO6·0.5H2O, the 1,4-dihydropyridine ring has a flattened boat conformation. The mean plane is almost perpendicular to the attached benzene ring, making a dihedral angle of 86.87 (9)°. The terminal phenyl ring is inclined to the central benzene ring by 67.56 (12)°. In the crystal, molecules are bridged via O—H⋯O hydrogen bonds involving the partially occupied water molecule, and this arrangement is strengthened by a pair of N—H⋯O hydrogen bonds and C—H⋯O interactions. The ethyl atoms of one of the ethyl ester groups are disordered over two sites with an occupancy ratio of 0.716 (5):0.284 (5).
Related literature
For the biological activity of ester derivatives, see: Bi et al. (2012); Bartzatt et al. (2004); Anadu et al. (2006).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2004); cell APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).
Supporting information
10.1107/S1600536813004108/su2546sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536813004108/su2546Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536813004108/su2546Isup3.cml
A mixture of 3-phenyl-acrylic acid 4-formyl-phenyl ester (0.01 mol), ethyl acetoacetate (0.02 mol), and ammonium acetate (0.03 mol) in ethanol (30 ml) was refluxed for 8 h. After the reaction had completed, the mixture was quenched with an excess of water. The solid precipitated which separated was dried and recrystallized from ethanol, giving colourless block-like crystals.
The CH3-CH2- atoms of one of the ethylester groups (C27 and C28) are disordered over two sites with an occupancy ratio of 0.716 (5):0.284 (5). The NH H atom was located in a difference Fourier map and refined with Uiso(H) = 1.2Ueq(N). The C-bound H atoms were positioned geometrically and constrained to ride on their parent atom: C–H = 0.93, 0.98, 0.97 and 0.96 Å for aromatic, methine, methylene and methyl H atoms, respectively, with Uiso(H) = 1.5Ueq(C) for methyl H atoms and = 1.2Ueq(C) for other H atoms. An isolated half water molecule (O1W) was refined isotropically with an occupancy of 0.5.
Data collection: APEX2 (Bruker, 2004); cell
APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).C28H29NO6·0.5H2O | F(000) = 2056 |
Mr = 484.53 | Dx = 1.259 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 8834 reflections |
a = 25.4905 (11) Å | θ = 2.1–31.2° |
b = 8.6166 (4) Å | µ = 0.09 mm−1 |
c = 23.2902 (10) Å | T = 293 K |
β = 92.235 (2)° | Block, colourless |
V = 5111.6 (4) Å3 | 0.25 × 0.20 × 0.20 mm |
Z = 8 |
Bruker Kappa APEXII CCD diffractometer | 5036 independent reflections |
Radiation source: fine-focus sealed tube | 3271 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ω and ϕ scan | θmax = 26.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker 2004) | h = −31→21 |
Tmin = 0.979, Tmax = 0.983 | k = −10→10 |
24059 measured reflections | l = −28→27 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.146 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0654P)2 + 1.6916P] where P = (Fo2 + 2Fc2)/3 |
5036 reflections | (Δ/σ)max = 0.008 |
344 parameters | Δρmax = 0.18 e Å−3 |
2 restraints | Δρmin = −0.31 e Å−3 |
C28H29NO6·0.5H2O | V = 5111.6 (4) Å3 |
Mr = 484.53 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 25.4905 (11) Å | µ = 0.09 mm−1 |
b = 8.6166 (4) Å | T = 293 K |
c = 23.2902 (10) Å | 0.25 × 0.20 × 0.20 mm |
β = 92.235 (2)° |
Bruker Kappa APEXII CCD diffractometer | 5036 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker 2004) | 3271 reflections with I > 2σ(I) |
Tmin = 0.979, Tmax = 0.983 | Rint = 0.027 |
24059 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 2 restraints |
wR(F2) = 0.146 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | Δρmax = 0.18 e Å−3 |
5036 reflections | Δρmin = −0.31 e Å−3 |
344 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.15295 (6) | 0.1181 (2) | 0.38244 (6) | 0.0831 (6) | |
O2 | 0.20401 (5) | 0.0099 (2) | 0.31780 (6) | 0.0765 (6) | |
O3 | 0.12749 (6) | 0.0181 (2) | 0.05234 (7) | 0.0902 (7) | |
O4 | 0.06211 (5) | −0.14990 (17) | 0.04359 (6) | 0.0727 (5) | |
O5 | 0.03119 (9) | 0.5972 (2) | 0.17358 (9) | 0.1146 (9) | |
O6 | 0.10758 (7) | 0.50789 (18) | 0.14631 (8) | 0.0950 (7) | |
N1 | −0.03049 (6) | 0.1524 (2) | 0.13608 (7) | 0.0614 (6) | |
C1 | 0.26807 (8) | −0.0271 (3) | 0.51329 (8) | 0.0651 (7) | |
C2 | 0.26107 (10) | 0.0205 (4) | 0.56879 (10) | 0.0966 (10) | |
C3 | 0.29518 (13) | −0.0298 (4) | 0.61298 (11) | 0.1089 (13) | |
C4 | 0.33541 (12) | −0.1280 (4) | 0.60133 (13) | 0.0984 (11) | |
C5 | 0.34198 (10) | −0.1753 (3) | 0.54686 (13) | 0.0945 (11) | |
C6 | 0.30910 (8) | −0.1260 (3) | 0.50304 (10) | 0.0761 (8) | |
C7 | 0.23098 (7) | 0.0247 (3) | 0.46755 (9) | 0.0661 (7) | |
C8 | 0.23225 (7) | −0.0054 (2) | 0.41294 (8) | 0.0610 (7) | |
C9 | 0.19188 (7) | 0.0489 (3) | 0.37172 (8) | 0.0603 (7) | |
C10 | 0.17077 (7) | 0.0613 (3) | 0.27168 (8) | 0.0617 (7) | |
C11 | 0.19264 (8) | 0.1538 (3) | 0.23170 (9) | 0.0793 (9) | |
C12 | 0.16255 (8) | 0.1999 (3) | 0.18433 (9) | 0.0749 (8) | |
C13 | 0.11058 (6) | 0.1577 (2) | 0.17750 (7) | 0.0510 (6) | |
C14 | 0.09000 (7) | 0.0638 (2) | 0.21843 (7) | 0.0540 (6) | |
C15 | 0.12003 (7) | 0.0140 (2) | 0.26555 (8) | 0.0597 (7) | |
C16 | 0.07650 (7) | 0.2137 (2) | 0.12629 (7) | 0.0533 (6) | |
C17 | 0.03766 (7) | 0.3350 (2) | 0.14437 (7) | 0.0555 (6) | |
C18 | −0.01294 (8) | 0.2973 (2) | 0.15185 (8) | 0.0583 (7) | |
C19 | −0.00213 (7) | 0.0484 (2) | 0.10495 (7) | 0.0536 (6) | |
C20 | 0.04903 (7) | 0.0777 (2) | 0.09681 (7) | 0.0510 (6) | |
C21 | 0.08341 (8) | −0.0176 (3) | 0.06266 (7) | 0.0589 (7) | |
C22 | 0.09348 (9) | −0.2500 (3) | 0.00904 (10) | 0.0840 (9) | |
C23 | 0.06010 (12) | −0.3865 (3) | −0.00605 (12) | 0.1018 (11) | |
C24 | −0.03430 (8) | −0.0877 (3) | 0.08445 (9) | 0.0702 (8) | |
C25 | −0.05506 (9) | 0.3959 (3) | 0.17583 (11) | 0.0842 (9) | |
C26 | 0.05650 (11) | 0.4907 (3) | 0.15686 (9) | 0.0737 (9) | |
C27A | 0.1365 (2) | 0.6471 (6) | 0.1590 (2) | 0.091 (2) | 0.716 (5) |
C28A | 0.15865 (17) | 0.6335 (5) | 0.2190 (2) | 0.1116 (19) | 0.716 (5) |
C28B | 0.1719 (5) | 0.6871 (14) | 0.1717 (6) | 0.1116 (19) | 0.284 (5) |
C27B | 0.1144 (5) | 0.6777 (12) | 0.1772 (5) | 0.072 (4) | 0.284 (5) |
O1W | −0.0134 (3) | 0.8162 (4) | 0.2322 (3) | 0.143 (4) | 0.500 |
H3 | 0.29060 | 0.00340 | 0.65040 | 0.1310* | |
H4 | 0.35820 | −0.16220 | 0.63080 | 0.1180* | |
H2 | 0.23350 | 0.08660 | 0.57680 | 0.1160* | |
H6 | 0.31440 | −0.15950 | 0.46580 | 0.0910* | |
H7 | 0.20330 | 0.08640 | 0.47890 | 0.0790* | |
H5 | 0.36930 | −0.24260 | 0.53910 | 0.1130* | |
H11 | 0.22740 | 0.18550 | 0.23630 | 0.0950* | |
H12 | 0.17760 | 0.26060 | 0.15640 | 0.0900* | |
H14 | 0.05510 | 0.03300 | 0.21440 | 0.0650* | |
H15 | 0.10570 | −0.05090 | 0.29270 | 0.0720* | |
H16 | 0.09960 | 0.26170 | 0.09870 | 0.0640* | |
H22A | 0.12500 | −0.28220 | 0.03050 | 0.1010* | |
H8 | 0.26000 | −0.06390 | 0.39970 | 0.0730* | |
H1N | −0.0639 (6) | 0.136 (2) | 0.1384 (9) | 0.0740* | |
H23B | 0.02800 | −0.35200 | −0.02490 | 0.1530* | |
H23C | 0.05220 | −0.44200 | 0.02830 | 0.1530* | |
H24A | −0.07040 | −0.07110 | 0.09310 | 0.1050* | |
H24B | −0.02170 | −0.18010 | 0.10340 | 0.1050* | |
H24C | −0.03150 | −0.09900 | 0.04370 | 0.1050* | |
H25A | −0.08780 | 0.34060 | 0.17370 | 0.1260* | |
H25B | −0.05840 | 0.49020 | 0.15400 | 0.1260* | |
H25C | −0.04600 | 0.42040 | 0.21520 | 0.1260* | |
H27A | 0.11360 | 0.73670 | 0.15550 | 0.1090* | 0.716 (5) |
H27B | 0.16460 | 0.65930 | 0.13240 | 0.1090* | 0.716 (5) |
H28A | 0.13050 | 0.63070 | 0.24520 | 0.1680* | 0.716 (5) |
H28B | 0.18080 | 0.72120 | 0.22770 | 0.1680* | 0.716 (5) |
H28C | 0.17890 | 0.53980 | 0.22280 | 0.1680* | 0.716 (5) |
H22B | 0.10370 | −0.19640 | −0.02540 | 0.1010* | |
H23A | 0.07850 | −0.45360 | −0.03130 | 0.1530* | |
H27C | 0.09580 | 0.75920 | 0.15620 | 0.0860* | 0.284 (5) |
H27D | 0.10430 | 0.67670 | 0.21690 | 0.0860* | 0.284 (5) |
H28D | 0.18840 | 0.60140 | 0.19160 | 0.1680* | 0.284 (5) |
H28E | 0.18470 | 0.78280 | 0.18820 | 0.1680* | 0.284 (5) |
H28F | 0.18010 | 0.68320 | 0.13180 | 0.1680* | 0.284 (5) |
H1W | 0.01850 | 0.74420 | 0.22660 | 0.2150* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0591 (9) | 0.1313 (14) | 0.0581 (8) | 0.0294 (9) | −0.0094 (7) | −0.0096 (8) |
O2 | 0.0594 (8) | 0.1200 (13) | 0.0496 (8) | 0.0294 (8) | −0.0052 (6) | 0.0052 (8) |
O3 | 0.0572 (9) | 0.1244 (14) | 0.0903 (11) | −0.0163 (9) | 0.0193 (8) | −0.0238 (10) |
O4 | 0.0681 (9) | 0.0813 (10) | 0.0693 (9) | −0.0021 (8) | 0.0110 (7) | −0.0154 (8) |
O5 | 0.1437 (17) | 0.0679 (11) | 0.1328 (17) | −0.0098 (12) | 0.0121 (14) | −0.0171 (11) |
O6 | 0.0896 (12) | 0.0735 (10) | 0.1188 (14) | −0.0290 (9) | −0.0366 (10) | 0.0151 (9) |
N1 | 0.0445 (8) | 0.0724 (11) | 0.0672 (10) | −0.0046 (8) | 0.0017 (7) | −0.0069 (8) |
C1 | 0.0518 (11) | 0.0847 (14) | 0.0578 (12) | −0.0103 (10) | −0.0103 (9) | 0.0094 (10) |
C2 | 0.0859 (17) | 0.139 (2) | 0.0634 (15) | 0.0026 (16) | −0.0145 (12) | −0.0060 (15) |
C3 | 0.114 (2) | 0.151 (3) | 0.0594 (15) | −0.025 (2) | −0.0245 (15) | 0.0058 (16) |
C4 | 0.0914 (19) | 0.105 (2) | 0.095 (2) | −0.0268 (16) | −0.0439 (16) | 0.0313 (16) |
C5 | 0.0811 (16) | 0.0976 (19) | 0.102 (2) | 0.0023 (14) | −0.0309 (14) | 0.0253 (16) |
C6 | 0.0664 (13) | 0.0879 (16) | 0.0727 (14) | 0.0054 (12) | −0.0143 (11) | 0.0142 (12) |
C7 | 0.0486 (10) | 0.0906 (15) | 0.0586 (12) | 0.0048 (10) | −0.0059 (9) | 0.0010 (10) |
C8 | 0.0473 (10) | 0.0794 (14) | 0.0559 (11) | 0.0081 (9) | −0.0033 (8) | 0.0072 (10) |
C9 | 0.0471 (10) | 0.0817 (14) | 0.0516 (11) | 0.0034 (10) | −0.0039 (8) | 0.0038 (10) |
C10 | 0.0518 (11) | 0.0883 (14) | 0.0443 (10) | 0.0166 (10) | −0.0059 (8) | 0.0008 (10) |
C11 | 0.0454 (11) | 0.129 (2) | 0.0627 (13) | −0.0076 (12) | −0.0089 (9) | 0.0161 (13) |
C12 | 0.0529 (11) | 0.1111 (18) | 0.0601 (12) | −0.0177 (11) | −0.0072 (9) | 0.0241 (12) |
C13 | 0.0466 (9) | 0.0619 (11) | 0.0440 (9) | −0.0036 (8) | −0.0032 (7) | 0.0011 (8) |
C14 | 0.0469 (9) | 0.0667 (12) | 0.0481 (10) | −0.0043 (8) | −0.0025 (8) | 0.0009 (9) |
C15 | 0.0597 (12) | 0.0736 (13) | 0.0459 (10) | 0.0013 (9) | 0.0017 (8) | 0.0070 (9) |
C16 | 0.0486 (10) | 0.0658 (12) | 0.0450 (9) | −0.0115 (9) | −0.0052 (7) | 0.0077 (8) |
C17 | 0.0606 (11) | 0.0602 (11) | 0.0444 (9) | −0.0046 (9) | −0.0136 (8) | 0.0061 (8) |
C18 | 0.0618 (12) | 0.0621 (12) | 0.0501 (10) | 0.0050 (9) | −0.0097 (8) | 0.0007 (9) |
C19 | 0.0493 (10) | 0.0658 (12) | 0.0454 (9) | −0.0039 (9) | −0.0034 (8) | 0.0000 (8) |
C20 | 0.0476 (10) | 0.0656 (12) | 0.0393 (9) | −0.0069 (8) | −0.0048 (7) | 0.0035 (8) |
C21 | 0.0536 (11) | 0.0802 (14) | 0.0426 (10) | −0.0034 (10) | −0.0036 (8) | 0.0012 (9) |
C22 | 0.0838 (15) | 0.1019 (18) | 0.0666 (13) | 0.0154 (14) | 0.0085 (11) | −0.0132 (13) |
C23 | 0.135 (2) | 0.0873 (18) | 0.0831 (17) | 0.0083 (17) | 0.0029 (16) | −0.0220 (14) |
C24 | 0.0535 (11) | 0.0794 (14) | 0.0772 (14) | −0.0121 (10) | −0.0018 (10) | −0.0123 (11) |
C25 | 0.0754 (15) | 0.0865 (17) | 0.0900 (16) | 0.0186 (12) | −0.0045 (12) | −0.0134 (13) |
C26 | 0.0996 (18) | 0.0606 (14) | 0.0589 (12) | −0.0084 (13) | −0.0206 (12) | 0.0097 (10) |
C27A | 0.083 (4) | 0.076 (3) | 0.113 (4) | −0.016 (3) | 0.000 (2) | −0.011 (3) |
C28A | 0.098 (3) | 0.097 (3) | 0.136 (4) | −0.003 (2) | −0.044 (3) | −0.029 (3) |
C28B | 0.098 (3) | 0.097 (3) | 0.136 (4) | −0.003 (2) | −0.044 (3) | −0.029 (3) |
C27B | 0.076 (7) | 0.059 (6) | 0.081 (7) | −0.015 (5) | 0.003 (5) | −0.012 (5) |
O1W | 0.179 (8) | 0.082 (2) | 0.175 (8) | 0.041 (3) | 0.095 (6) | 0.024 (3) |
O1—C9 | 1.193 (3) | C20—C21 | 1.459 (3) |
O2—C9 | 1.348 (2) | C22—C23 | 1.486 (4) |
O2—C10 | 1.413 (2) | C27A—C28A | 1.491 (7) |
O3—C21 | 1.198 (3) | C27B—C28B | 1.479 (18) |
O4—C21 | 1.332 (3) | C2—H2 | 0.9300 |
O4—C22 | 1.443 (3) | C3—H3 | 0.9300 |
O5—C26 | 1.196 (3) | C4—H4 | 0.9300 |
O6—C26 | 1.343 (3) | C5—H5 | 0.9300 |
O6—C27A | 1.433 (5) | C6—H6 | 0.9300 |
O6—C27B | 1.637 (11) | C7—H7 | 0.9300 |
O1W—H1W | 1.0400 | C8—H8 | 0.9300 |
O1W—H1Wi | 1.1500 | C11—H11 | 0.9300 |
N1—C19 | 1.376 (2) | C12—H12 | 0.9300 |
N1—C18 | 1.372 (2) | C14—H14 | 0.9300 |
N1—H1N | 0.867 (15) | C15—H15 | 0.9300 |
C1—C2 | 1.374 (3) | C16—H16 | 0.9800 |
C1—C7 | 1.466 (3) | C22—H22B | 0.9700 |
C1—C6 | 1.377 (3) | C22—H22A | 0.9700 |
C2—C3 | 1.390 (4) | C23—H23A | 0.9600 |
C3—C4 | 1.365 (5) | C23—H23B | 0.9600 |
C4—C5 | 1.349 (4) | C23—H23C | 0.9600 |
C5—C6 | 1.363 (4) | C24—H24A | 0.9600 |
C7—C8 | 1.300 (3) | C24—H24C | 0.9600 |
C8—C9 | 1.457 (3) | C24—H24B | 0.9600 |
C10—C15 | 1.358 (3) | C25—H25B | 0.9600 |
C10—C11 | 1.362 (3) | C25—H25C | 0.9600 |
C11—C12 | 1.377 (3) | C25—H25A | 0.9600 |
C12—C13 | 1.377 (3) | C27A—H27A | 0.9700 |
C13—C16 | 1.526 (2) | C27A—H27B | 0.9700 |
C13—C14 | 1.370 (2) | C27B—H27C | 0.9700 |
C14—C15 | 1.382 (2) | C27B—H27D | 0.9700 |
C16—C17 | 1.511 (2) | C28A—H28A | 0.9600 |
C16—C20 | 1.516 (2) | C28A—H28B | 0.9600 |
C17—C26 | 1.451 (3) | C28A—H28C | 0.9600 |
C17—C18 | 1.348 (3) | C28B—H28F | 0.9600 |
C18—C25 | 1.494 (3) | C28B—H28D | 0.9600 |
C19—C24 | 1.498 (3) | C28B—H28E | 0.9600 |
C19—C20 | 1.349 (3) | ||
C9—O2—C10 | 118.53 (16) | C5—C6—H6 | 120.00 |
C21—O4—C22 | 118.05 (16) | C1—C6—H6 | 120.00 |
C26—O6—C27A | 123.3 (3) | C8—C7—H7 | 116.00 |
C26—O6—C27B | 96.1 (5) | C1—C7—H7 | 116.00 |
H1W—O1W—H1Wi | 84.00 | C7—C8—H8 | 119.00 |
C18—N1—C19 | 124.16 (16) | C9—C8—H8 | 119.00 |
C18—N1—H1N | 116.3 (12) | C12—C11—H11 | 120.00 |
C19—N1—H1N | 117.7 (12) | C10—C11—H11 | 120.00 |
C2—C1—C6 | 118.4 (2) | C11—C12—H12 | 119.00 |
C6—C1—C7 | 122.35 (19) | C13—C12—H12 | 119.00 |
C2—C1—C7 | 119.3 (2) | C15—C14—H14 | 119.00 |
C1—C2—C3 | 120.2 (3) | C13—C14—H14 | 119.00 |
C2—C3—C4 | 119.9 (3) | C10—C15—H15 | 120.00 |
C3—C4—C5 | 119.7 (3) | C14—C15—H15 | 120.00 |
C4—C5—C6 | 121.0 (3) | C13—C16—H16 | 108.00 |
C1—C6—C5 | 120.8 (2) | C17—C16—H16 | 108.00 |
C1—C7—C8 | 127.62 (19) | C20—C16—H16 | 108.00 |
C7—C8—C9 | 122.47 (18) | O4—C22—H22B | 110.00 |
O2—C9—C8 | 110.62 (16) | C23—C22—H22A | 111.00 |
O1—C9—C8 | 126.50 (18) | C23—C22—H22B | 111.00 |
O1—C9—O2 | 122.88 (17) | H22A—C22—H22B | 109.00 |
O2—C10—C11 | 117.00 (17) | O4—C22—H22A | 110.00 |
O2—C10—C15 | 121.74 (18) | C22—C23—H23A | 109.00 |
C11—C10—C15 | 121.16 (18) | C22—C23—H23B | 109.00 |
C10—C11—C12 | 119.12 (19) | H23A—C23—H23B | 110.00 |
C11—C12—C13 | 121.3 (2) | H23A—C23—H23C | 109.00 |
C12—C13—C16 | 121.50 (16) | H23B—C23—H23C | 109.00 |
C14—C13—C16 | 120.58 (15) | C22—C23—H23C | 110.00 |
C12—C13—C14 | 117.92 (17) | C19—C24—H24B | 109.00 |
C13—C14—C15 | 121.38 (16) | C19—C24—H24C | 109.00 |
C10—C15—C14 | 119.08 (17) | C19—C24—H24A | 109.00 |
C13—C16—C20 | 110.39 (14) | H24A—C24—H24C | 109.00 |
C17—C16—C20 | 111.40 (15) | H24B—C24—H24C | 110.00 |
C13—C16—C17 | 111.11 (13) | H24A—C24—H24B | 109.00 |
C18—C17—C26 | 120.53 (18) | C18—C25—H25B | 109.00 |
C16—C17—C26 | 118.71 (17) | C18—C25—H25C | 109.00 |
C16—C17—C18 | 120.67 (16) | C18—C25—H25A | 110.00 |
N1—C18—C17 | 119.24 (17) | H25A—C25—H25C | 110.00 |
N1—C18—C25 | 112.71 (18) | H25B—C25—H25C | 109.00 |
C17—C18—C25 | 128.05 (17) | H25A—C25—H25B | 109.00 |
C20—C19—C24 | 128.45 (17) | O6—C27A—H27B | 110.00 |
N1—C19—C24 | 112.67 (16) | C28A—C27A—H27A | 110.00 |
N1—C19—C20 | 118.88 (16) | C28A—C27A—H27B | 110.00 |
C16—C20—C19 | 120.87 (15) | H27A—C27A—H27B | 108.00 |
C16—C20—C21 | 113.91 (16) | O6—C27A—H27A | 110.00 |
C19—C20—C21 | 125.15 (17) | O6—C27B—H27D | 113.00 |
O3—C21—O4 | 121.8 (2) | C28B—C27B—H27C | 113.00 |
O3—C21—C20 | 123.6 (2) | H27C—C27B—H27D | 110.00 |
O4—C21—C20 | 114.70 (17) | O6—C27B—H27C | 113.00 |
O4—C22—C23 | 106.29 (19) | C28B—C27B—H27D | 113.00 |
O5—C26—C17 | 126.6 (3) | H28A—C28A—H28C | 109.00 |
O5—C26—O6 | 121.0 (2) | H28B—C28A—H28C | 109.00 |
O6—C26—C17 | 112.4 (2) | C27A—C28A—H28A | 109.00 |
O6—C27A—C28A | 107.5 (4) | C27A—C28A—H28B | 110.00 |
O6—C27B—C28B | 95.7 (8) | H28A—C28A—H28B | 109.00 |
C3—C2—H2 | 120.00 | C27A—C28A—H28C | 110.00 |
C1—C2—H2 | 120.00 | C27B—C28B—H28E | 110.00 |
C2—C3—H3 | 120.00 | C27B—C28B—H28F | 110.00 |
C4—C3—H3 | 120.00 | C27B—C28B—H28D | 109.00 |
C5—C4—H4 | 120.00 | H28D—C28B—H28F | 109.00 |
C3—C4—H4 | 120.00 | H28E—C28B—H28F | 109.00 |
C4—C5—H5 | 120.00 | H28D—C28B—H28E | 109.00 |
C6—C5—H5 | 119.00 | ||
C10—O2—C9—O1 | 3.9 (3) | C11—C12—C13—C16 | 177.6 (2) |
C10—O2—C9—C8 | −176.27 (18) | C12—C13—C14—C15 | 0.7 (3) |
C9—O2—C10—C11 | 119.8 (2) | C16—C13—C14—C15 | −178.96 (16) |
C9—O2—C10—C15 | −63.7 (3) | C12—C13—C16—C17 | −107.2 (2) |
C22—O4—C21—O3 | −0.8 (3) | C12—C13—C16—C20 | 128.71 (19) |
C22—O4—C21—C20 | 179.46 (16) | C14—C13—C16—C17 | 72.5 (2) |
C21—O4—C22—C23 | −179.81 (18) | C14—C13—C16—C20 | −51.6 (2) |
C27A—O6—C26—O5 | 6.0 (4) | C13—C14—C15—C10 | 1.0 (3) |
C27A—O6—C26—C17 | −175.4 (3) | C13—C16—C17—C18 | −101.32 (19) |
C26—O6—C27A—C28A | 89.2 (4) | C13—C16—C17—C26 | 75.0 (2) |
C19—N1—C18—C17 | −10.2 (3) | C20—C16—C17—C18 | 22.2 (2) |
C19—N1—C18—C25 | 169.52 (18) | C20—C16—C17—C26 | −161.42 (16) |
C18—N1—C19—C20 | 11.1 (3) | C13—C16—C20—C19 | 102.65 (18) |
C18—N1—C19—C24 | −169.25 (17) | C13—C16—C20—C21 | −74.51 (18) |
C6—C1—C2—C3 | 0.6 (4) | C17—C16—C20—C19 | −21.3 (2) |
C7—C1—C2—C3 | 178.7 (3) | C17—C16—C20—C21 | 161.55 (15) |
C2—C1—C6—C5 | −0.1 (4) | C16—C17—C18—N1 | −8.0 (3) |
C7—C1—C6—C5 | −178.1 (2) | C16—C17—C18—C25 | 172.33 (19) |
C2—C1—C7—C8 | 178.2 (3) | C26—C17—C18—N1 | 175.67 (17) |
C6—C1—C7—C8 | −3.8 (4) | C26—C17—C18—C25 | −4.0 (3) |
C1—C2—C3—C4 | −0.7 (5) | C16—C17—C26—O5 | −177.1 (2) |
C2—C3—C4—C5 | 0.3 (5) | C16—C17—C26—O6 | 4.4 (3) |
C3—C4—C5—C6 | 0.3 (5) | C18—C17—C26—O5 | −0.7 (3) |
C4—C5—C6—C1 | −0.4 (4) | C18—C17—C26—O6 | −179.25 (18) |
C1—C7—C8—C9 | 177.9 (2) | N1—C19—C20—C16 | 6.2 (2) |
C7—C8—C9—O1 | −3.8 (4) | N1—C19—C20—C21 | −177.00 (17) |
C7—C8—C9—O2 | 176.4 (2) | C24—C19—C20—C16 | −173.42 (17) |
O2—C10—C11—C12 | 176.5 (2) | C24—C19—C20—C21 | 3.4 (3) |
C15—C10—C11—C12 | 0.1 (4) | C16—C20—C21—O3 | −9.3 (3) |
O2—C10—C15—C14 | −177.68 (18) | C16—C20—C21—O4 | 170.37 (15) |
C11—C10—C15—C14 | −1.4 (3) | C19—C20—C21—O3 | 173.65 (19) |
C10—C11—C12—C13 | 1.8 (4) | C19—C20—C21—O4 | −6.7 (3) |
C11—C12—C13—C14 | −2.1 (3) |
Symmetry code: (i) −x, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.87 (2) | 2.31 (2) | 3.148 (2) | 163 (2) |
O1W—H1W···O5 | 1.04 | 1.81 | 2.615 (6) | 132 |
C14—H14···O1Wii | 0.93 | 2.50 | 3.140 (6) | 126 |
Symmetry codes: (i) −x, y, −z+1/2; (ii) −x, y−1, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C28H29NO6·0.5H2O |
Mr | 484.53 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 25.4905 (11), 8.6166 (4), 23.2902 (10) |
β (°) | 92.235 (2) |
V (Å3) | 5111.6 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.25 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker 2004) |
Tmin, Tmax | 0.979, 0.983 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 24059, 5036, 3271 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.146, 1.09 |
No. of reflections | 5036 |
No. of parameters | 344 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.18, −0.31 |
Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.867 (15) | 2.308 (16) | 3.148 (2) | 163.4 (18) |
O1W—H1W···O5 | 1.04 | 1.81 | 2.615 (6) | 132 |
C14—H14···O1Wii | 0.93 | 2.50 | 3.140 (6) | 126 |
Symmetry codes: (i) −x, y, −z+1/2; (ii) −x, y−1, −z+1/2. |
Acknowledgements
SA thanks the UGC, India, for financial support
References
Anadu, N. O., Davisson, V. J. & Cushman, M. (2006). J. Med. Chem. 49, 3897–3905. Web of Science CrossRef PubMed CAS Google Scholar
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Ester derivatives of many compounds exhibit a variety of pharmacological properties, for example anticancer, antitumor and antimicrobial activities (Anadu et al., 2006; Bi et al., 2012; Bartzatt et al., 2004). In view of their importance, the title compound was synthesized and we report herein on its crystal structure.
In the title molecule (Fig. 1) the 1,4-dihydropyridine ring (N1/C16-C20) mean plane is almost perpendicular to the attached benzene ring (C10-C15), with a dihedral angle of 86.87 (9)°. This central benzene ring makes a dihedral angle of 67.56 (12)° with the terminal phenyl ring (C1-C6).
In the crystal, molecules are linked via O-H···O hydrogen bonds involving the water molecule, and this arrangement is strengthened by a pair of N-H···O hydrogen bonds and C-H···O interactions (Fig. 2 and Table 1).