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

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ISSN: 2056-9890

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

(Received 27 December 2012; accepted 11 February 2013; online 16 February 2013)

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[Bi, Y., Xu, J., Sun, F., Wu, X., Ye, W., Sun, Y. & Huang, W. (2012). Molecules, 17, 8832-8841.]); Bartzatt et al. (2004[Bartzatt, R., Cirillo, S. L. & Cirillo, J. D. (2004). Physiol. Chem. Phys. Med. NMR, 36, 85-94.]); Anadu et al. (2006[Anadu, N. O., Davisson, V. J. & Cushman, M. (2006). J. Med. Chem. 49, 3897-3905.]).

[Scheme 1]

Experimental

Crystal data
  • C28H29NO6·0.5H2O

  • Mr = 484.53

  • Monoclinic, C 2/c

  • a = 25.4905 (11) Å

  • b = 8.6166 (4) Å

  • c = 23.2902 (10) Å

  • β = 92.235 (2)°

  • V = 5111.6 (4) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 K

  • 0.25 × 0.20 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.979, Tmax = 0.983

  • 24059 measured reflections

  • 5036 independent reflections

  • 3271 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.146

  • S = 1.09

  • 5036 reflections

  • 344 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.31 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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+{\script{1\over 2}}]; (ii) [-x, y-1, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

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).

Related literature top

For the biological activity of ester derivatives, see: Bi et al. (2012); Bartzatt et al. (2004); Anadu et al. (2006).

Experimental top

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.

Refinement top

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.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with the atom numbering. Displacement ellipsoids are drawn at the 30% probability level [H atoms have been omitted for clarity].
[Figure 2] Fig. 2. Crystal packing of the title compound viewed along the b axis. Hydrogen bonds are shown as dashed lines [for the sake of clarity, H atoms not involved in these interactions have been omitted].
Diethyl 2,6-dimethyl-4-[4-(3-phenylacryloyloxy)phenyl]-1,4-dihydropyridine-3,5-dicarboxylate hemihydrate top
Crystal data top
C28H29NO6·0.5H2OF(000) = 2056
Mr = 484.53Dx = 1.259 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 8834 reflections
a = 25.4905 (11) Åθ = 2.1–31.2°
b = 8.6166 (4) ŵ = 0.09 mm1
c = 23.2902 (10) ÅT = 293 K
β = 92.235 (2)°Block, colourless
V = 5111.6 (4) Å30.25 × 0.20 × 0.20 mm
Z = 8
Data collection top
Bruker Kappa APEXII CCD
diffractometer
5036 independent reflections
Radiation source: fine-focus sealed tube3271 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ω and ϕ scanθmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker 2004)
h = 3121
Tmin = 0.979, Tmax = 0.983k = 1010
24059 measured reflectionsl = 2827
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H 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 parametersΔρmax = 0.18 e Å3
2 restraintsΔρmin = 0.31 e Å3
Crystal data top
C28H29NO6·0.5H2OV = 5111.6 (4) Å3
Mr = 484.53Z = 8
Monoclinic, C2/cMo Kα radiation
a = 25.4905 (11) ŵ = 0.09 mm1
b = 8.6166 (4) ÅT = 293 K
c = 23.2902 (10) Å0.25 × 0.20 × 0.20 mm
β = 92.235 (2)°
Data collection top
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 = 0.983Rint = 0.027
24059 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0482 restraints
wR(F2) = 0.146H atoms treated by a mixture of independent and constrained refinement
S = 1.09Δρmax = 0.18 e Å3
5036 reflectionsΔρmin = 0.31 e Å3
344 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.15295 (6)0.1181 (2)0.38244 (6)0.0831 (6)
O20.20401 (5)0.0099 (2)0.31780 (6)0.0765 (6)
O30.12749 (6)0.0181 (2)0.05234 (7)0.0902 (7)
O40.06211 (5)0.14990 (17)0.04359 (6)0.0727 (5)
O50.03119 (9)0.5972 (2)0.17358 (9)0.1146 (9)
O60.10758 (7)0.50789 (18)0.14631 (8)0.0950 (7)
N10.03049 (6)0.1524 (2)0.13608 (7)0.0614 (6)
C10.26807 (8)0.0271 (3)0.51329 (8)0.0651 (7)
C20.26107 (10)0.0205 (4)0.56879 (10)0.0966 (10)
C30.29518 (13)0.0298 (4)0.61298 (11)0.1089 (13)
C40.33541 (12)0.1280 (4)0.60133 (13)0.0984 (11)
C50.34198 (10)0.1753 (3)0.54686 (13)0.0945 (11)
C60.30910 (8)0.1260 (3)0.50304 (10)0.0761 (8)
C70.23098 (7)0.0247 (3)0.46755 (9)0.0661 (7)
C80.23225 (7)0.0054 (2)0.41294 (8)0.0610 (7)
C90.19188 (7)0.0489 (3)0.37172 (8)0.0603 (7)
C100.17077 (7)0.0613 (3)0.27168 (8)0.0617 (7)
C110.19264 (8)0.1538 (3)0.23170 (9)0.0793 (9)
C120.16255 (8)0.1999 (3)0.18433 (9)0.0749 (8)
C130.11058 (6)0.1577 (2)0.17750 (7)0.0510 (6)
C140.09000 (7)0.0638 (2)0.21843 (7)0.0540 (6)
C150.12003 (7)0.0140 (2)0.26555 (8)0.0597 (7)
C160.07650 (7)0.2137 (2)0.12629 (7)0.0533 (6)
C170.03766 (7)0.3350 (2)0.14437 (7)0.0555 (6)
C180.01294 (8)0.2973 (2)0.15185 (8)0.0583 (7)
C190.00213 (7)0.0484 (2)0.10495 (7)0.0536 (6)
C200.04903 (7)0.0777 (2)0.09681 (7)0.0510 (6)
C210.08341 (8)0.0176 (3)0.06266 (7)0.0589 (7)
C220.09348 (9)0.2500 (3)0.00904 (10)0.0840 (9)
C230.06010 (12)0.3865 (3)0.00605 (12)0.1018 (11)
C240.03430 (8)0.0877 (3)0.08445 (9)0.0702 (8)
C250.05506 (9)0.3959 (3)0.17583 (11)0.0842 (9)
C260.05650 (11)0.4907 (3)0.15686 (9)0.0737 (9)
C27A0.1365 (2)0.6471 (6)0.1590 (2)0.091 (2)0.716 (5)
C28A0.15865 (17)0.6335 (5)0.2190 (2)0.1116 (19)0.716 (5)
C28B0.1719 (5)0.6871 (14)0.1717 (6)0.1116 (19)0.284 (5)
C27B0.1144 (5)0.6777 (12)0.1772 (5)0.072 (4)0.284 (5)
O1W0.0134 (3)0.8162 (4)0.2322 (3)0.143 (4)0.500
H30.290600.003400.650400.1310*
H40.358200.162200.630800.1180*
H20.233500.086600.576800.1160*
H60.314400.159500.465800.0910*
H70.203300.086400.478900.0790*
H50.369300.242600.539100.1130*
H110.227400.185500.236300.0950*
H120.177600.260600.156400.0900*
H140.055100.033000.214400.0650*
H150.105700.050900.292700.0720*
H160.099600.261700.098700.0640*
H22A0.125000.282200.030500.1010*
H80.260000.063900.399700.0730*
H1N0.0639 (6)0.136 (2)0.1384 (9)0.0740*
H23B0.028000.352000.024900.1530*
H23C0.052200.442000.028300.1530*
H24A0.070400.071100.093100.1050*
H24B0.021700.180100.103400.1050*
H24C0.031500.099000.043700.1050*
H25A0.087800.340600.173700.1260*
H25B0.058400.490200.154000.1260*
H25C0.046000.420400.215200.1260*
H27A0.113600.736700.155500.1090*0.716 (5)
H27B0.164600.659300.132400.1090*0.716 (5)
H28A0.130500.630700.245200.1680*0.716 (5)
H28B0.180800.721200.227700.1680*0.716 (5)
H28C0.178900.539800.222800.1680*0.716 (5)
H22B0.103700.196400.025400.1010*
H23A0.078500.453600.031300.1530*
H27C0.095800.759200.156200.0860*0.284 (5)
H27D0.104300.676700.216900.0860*0.284 (5)
H28D0.188400.601400.191600.1680*0.284 (5)
H28E0.184700.782800.188200.1680*0.284 (5)
H28F0.180100.683200.131800.1680*0.284 (5)
H1W0.018500.744200.226600.2150*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0591 (9)0.1313 (14)0.0581 (8)0.0294 (9)0.0094 (7)0.0096 (8)
O20.0594 (8)0.1200 (13)0.0496 (8)0.0294 (8)0.0052 (6)0.0052 (8)
O30.0572 (9)0.1244 (14)0.0903 (11)0.0163 (9)0.0193 (8)0.0238 (10)
O40.0681 (9)0.0813 (10)0.0693 (9)0.0021 (8)0.0110 (7)0.0154 (8)
O50.1437 (17)0.0679 (11)0.1328 (17)0.0098 (12)0.0121 (14)0.0171 (11)
O60.0896 (12)0.0735 (10)0.1188 (14)0.0290 (9)0.0366 (10)0.0151 (9)
N10.0445 (8)0.0724 (11)0.0672 (10)0.0046 (8)0.0017 (7)0.0069 (8)
C10.0518 (11)0.0847 (14)0.0578 (12)0.0103 (10)0.0103 (9)0.0094 (10)
C20.0859 (17)0.139 (2)0.0634 (15)0.0026 (16)0.0145 (12)0.0060 (15)
C30.114 (2)0.151 (3)0.0594 (15)0.025 (2)0.0245 (15)0.0058 (16)
C40.0914 (19)0.105 (2)0.095 (2)0.0268 (16)0.0439 (16)0.0313 (16)
C50.0811 (16)0.0976 (19)0.102 (2)0.0023 (14)0.0309 (14)0.0253 (16)
C60.0664 (13)0.0879 (16)0.0727 (14)0.0054 (12)0.0143 (11)0.0142 (12)
C70.0486 (10)0.0906 (15)0.0586 (12)0.0048 (10)0.0059 (9)0.0010 (10)
C80.0473 (10)0.0794 (14)0.0559 (11)0.0081 (9)0.0033 (8)0.0072 (10)
C90.0471 (10)0.0817 (14)0.0516 (11)0.0034 (10)0.0039 (8)0.0038 (10)
C100.0518 (11)0.0883 (14)0.0443 (10)0.0166 (10)0.0059 (8)0.0008 (10)
C110.0454 (11)0.129 (2)0.0627 (13)0.0076 (12)0.0089 (9)0.0161 (13)
C120.0529 (11)0.1111 (18)0.0601 (12)0.0177 (11)0.0072 (9)0.0241 (12)
C130.0466 (9)0.0619 (11)0.0440 (9)0.0036 (8)0.0032 (7)0.0011 (8)
C140.0469 (9)0.0667 (12)0.0481 (10)0.0043 (8)0.0025 (8)0.0009 (9)
C150.0597 (12)0.0736 (13)0.0459 (10)0.0013 (9)0.0017 (8)0.0070 (9)
C160.0486 (10)0.0658 (12)0.0450 (9)0.0115 (9)0.0052 (7)0.0077 (8)
C170.0606 (11)0.0602 (11)0.0444 (9)0.0046 (9)0.0136 (8)0.0061 (8)
C180.0618 (12)0.0621 (12)0.0501 (10)0.0050 (9)0.0097 (8)0.0007 (9)
C190.0493 (10)0.0658 (12)0.0454 (9)0.0039 (9)0.0034 (8)0.0000 (8)
C200.0476 (10)0.0656 (12)0.0393 (9)0.0069 (8)0.0048 (7)0.0035 (8)
C210.0536 (11)0.0802 (14)0.0426 (10)0.0034 (10)0.0036 (8)0.0012 (9)
C220.0838 (15)0.1019 (18)0.0666 (13)0.0154 (14)0.0085 (11)0.0132 (13)
C230.135 (2)0.0873 (18)0.0831 (17)0.0083 (17)0.0029 (16)0.0220 (14)
C240.0535 (11)0.0794 (14)0.0772 (14)0.0121 (10)0.0018 (10)0.0123 (11)
C250.0754 (15)0.0865 (17)0.0900 (16)0.0186 (12)0.0045 (12)0.0134 (13)
C260.0996 (18)0.0606 (14)0.0589 (12)0.0084 (13)0.0206 (12)0.0097 (10)
C27A0.083 (4)0.076 (3)0.113 (4)0.016 (3)0.000 (2)0.011 (3)
C28A0.098 (3)0.097 (3)0.136 (4)0.003 (2)0.044 (3)0.029 (3)
C28B0.098 (3)0.097 (3)0.136 (4)0.003 (2)0.044 (3)0.029 (3)
C27B0.076 (7)0.059 (6)0.081 (7)0.015 (5)0.003 (5)0.012 (5)
O1W0.179 (8)0.082 (2)0.175 (8)0.041 (3)0.095 (6)0.024 (3)
Geometric parameters (Å, º) top
O1—C91.193 (3)C20—C211.459 (3)
O2—C91.348 (2)C22—C231.486 (4)
O2—C101.413 (2)C27A—C28A1.491 (7)
O3—C211.198 (3)C27B—C28B1.479 (18)
O4—C211.332 (3)C2—H20.9300
O4—C221.443 (3)C3—H30.9300
O5—C261.196 (3)C4—H40.9300
O6—C261.343 (3)C5—H50.9300
O6—C27A1.433 (5)C6—H60.9300
O6—C27B1.637 (11)C7—H70.9300
O1W—H1W1.0400C8—H80.9300
O1W—H1Wi1.1500C11—H110.9300
N1—C191.376 (2)C12—H120.9300
N1—C181.372 (2)C14—H140.9300
N1—H1N0.867 (15)C15—H150.9300
C1—C21.374 (3)C16—H160.9800
C1—C71.466 (3)C22—H22B0.9700
C1—C61.377 (3)C22—H22A0.9700
C2—C31.390 (4)C23—H23A0.9600
C3—C41.365 (5)C23—H23B0.9600
C4—C51.349 (4)C23—H23C0.9600
C5—C61.363 (4)C24—H24A0.9600
C7—C81.300 (3)C24—H24C0.9600
C8—C91.457 (3)C24—H24B0.9600
C10—C151.358 (3)C25—H25B0.9600
C10—C111.362 (3)C25—H25C0.9600
C11—C121.377 (3)C25—H25A0.9600
C12—C131.377 (3)C27A—H27A0.9700
C13—C161.526 (2)C27A—H27B0.9700
C13—C141.370 (2)C27B—H27C0.9700
C14—C151.382 (2)C27B—H27D0.9700
C16—C171.511 (2)C28A—H28A0.9600
C16—C201.516 (2)C28A—H28B0.9600
C17—C261.451 (3)C28A—H28C0.9600
C17—C181.348 (3)C28B—H28F0.9600
C18—C251.494 (3)C28B—H28D0.9600
C19—C241.498 (3)C28B—H28E0.9600
C19—C201.349 (3)
C9—O2—C10118.53 (16)C5—C6—H6120.00
C21—O4—C22118.05 (16)C1—C6—H6120.00
C26—O6—C27A123.3 (3)C8—C7—H7116.00
C26—O6—C27B96.1 (5)C1—C7—H7116.00
H1W—O1W—H1Wi84.00C7—C8—H8119.00
C18—N1—C19124.16 (16)C9—C8—H8119.00
C18—N1—H1N116.3 (12)C12—C11—H11120.00
C19—N1—H1N117.7 (12)C10—C11—H11120.00
C2—C1—C6118.4 (2)C11—C12—H12119.00
C6—C1—C7122.35 (19)C13—C12—H12119.00
C2—C1—C7119.3 (2)C15—C14—H14119.00
C1—C2—C3120.2 (3)C13—C14—H14119.00
C2—C3—C4119.9 (3)C10—C15—H15120.00
C3—C4—C5119.7 (3)C14—C15—H15120.00
C4—C5—C6121.0 (3)C13—C16—H16108.00
C1—C6—C5120.8 (2)C17—C16—H16108.00
C1—C7—C8127.62 (19)C20—C16—H16108.00
C7—C8—C9122.47 (18)O4—C22—H22B110.00
O2—C9—C8110.62 (16)C23—C22—H22A111.00
O1—C9—C8126.50 (18)C23—C22—H22B111.00
O1—C9—O2122.88 (17)H22A—C22—H22B109.00
O2—C10—C11117.00 (17)O4—C22—H22A110.00
O2—C10—C15121.74 (18)C22—C23—H23A109.00
C11—C10—C15121.16 (18)C22—C23—H23B109.00
C10—C11—C12119.12 (19)H23A—C23—H23B110.00
C11—C12—C13121.3 (2)H23A—C23—H23C109.00
C12—C13—C16121.50 (16)H23B—C23—H23C109.00
C14—C13—C16120.58 (15)C22—C23—H23C110.00
C12—C13—C14117.92 (17)C19—C24—H24B109.00
C13—C14—C15121.38 (16)C19—C24—H24C109.00
C10—C15—C14119.08 (17)C19—C24—H24A109.00
C13—C16—C20110.39 (14)H24A—C24—H24C109.00
C17—C16—C20111.40 (15)H24B—C24—H24C110.00
C13—C16—C17111.11 (13)H24A—C24—H24B109.00
C18—C17—C26120.53 (18)C18—C25—H25B109.00
C16—C17—C26118.71 (17)C18—C25—H25C109.00
C16—C17—C18120.67 (16)C18—C25—H25A110.00
N1—C18—C17119.24 (17)H25A—C25—H25C110.00
N1—C18—C25112.71 (18)H25B—C25—H25C109.00
C17—C18—C25128.05 (17)H25A—C25—H25B109.00
C20—C19—C24128.45 (17)O6—C27A—H27B110.00
N1—C19—C24112.67 (16)C28A—C27A—H27A110.00
N1—C19—C20118.88 (16)C28A—C27A—H27B110.00
C16—C20—C19120.87 (15)H27A—C27A—H27B108.00
C16—C20—C21113.91 (16)O6—C27A—H27A110.00
C19—C20—C21125.15 (17)O6—C27B—H27D113.00
O3—C21—O4121.8 (2)C28B—C27B—H27C113.00
O3—C21—C20123.6 (2)H27C—C27B—H27D110.00
O4—C21—C20114.70 (17)O6—C27B—H27C113.00
O4—C22—C23106.29 (19)C28B—C27B—H27D113.00
O5—C26—C17126.6 (3)H28A—C28A—H28C109.00
O5—C26—O6121.0 (2)H28B—C28A—H28C109.00
O6—C26—C17112.4 (2)C27A—C28A—H28A109.00
O6—C27A—C28A107.5 (4)C27A—C28A—H28B110.00
O6—C27B—C28B95.7 (8)H28A—C28A—H28B109.00
C3—C2—H2120.00C27A—C28A—H28C110.00
C1—C2—H2120.00C27B—C28B—H28E110.00
C2—C3—H3120.00C27B—C28B—H28F110.00
C4—C3—H3120.00C27B—C28B—H28D109.00
C5—C4—H4120.00H28D—C28B—H28F109.00
C3—C4—H4120.00H28E—C28B—H28F109.00
C4—C5—H5120.00H28D—C28B—H28E109.00
C6—C5—H5119.00
C10—O2—C9—O13.9 (3)C11—C12—C13—C16177.6 (2)
C10—O2—C9—C8176.27 (18)C12—C13—C14—C150.7 (3)
C9—O2—C10—C11119.8 (2)C16—C13—C14—C15178.96 (16)
C9—O2—C10—C1563.7 (3)C12—C13—C16—C17107.2 (2)
C22—O4—C21—O30.8 (3)C12—C13—C16—C20128.71 (19)
C22—O4—C21—C20179.46 (16)C14—C13—C16—C1772.5 (2)
C21—O4—C22—C23179.81 (18)C14—C13—C16—C2051.6 (2)
C27A—O6—C26—O56.0 (4)C13—C14—C15—C101.0 (3)
C27A—O6—C26—C17175.4 (3)C13—C16—C17—C18101.32 (19)
C26—O6—C27A—C28A89.2 (4)C13—C16—C17—C2675.0 (2)
C19—N1—C18—C1710.2 (3)C20—C16—C17—C1822.2 (2)
C19—N1—C18—C25169.52 (18)C20—C16—C17—C26161.42 (16)
C18—N1—C19—C2011.1 (3)C13—C16—C20—C19102.65 (18)
C18—N1—C19—C24169.25 (17)C13—C16—C20—C2174.51 (18)
C6—C1—C2—C30.6 (4)C17—C16—C20—C1921.3 (2)
C7—C1—C2—C3178.7 (3)C17—C16—C20—C21161.55 (15)
C2—C1—C6—C50.1 (4)C16—C17—C18—N18.0 (3)
C7—C1—C6—C5178.1 (2)C16—C17—C18—C25172.33 (19)
C2—C1—C7—C8178.2 (3)C26—C17—C18—N1175.67 (17)
C6—C1—C7—C83.8 (4)C26—C17—C18—C254.0 (3)
C1—C2—C3—C40.7 (5)C16—C17—C26—O5177.1 (2)
C2—C3—C4—C50.3 (5)C16—C17—C26—O64.4 (3)
C3—C4—C5—C60.3 (5)C18—C17—C26—O50.7 (3)
C4—C5—C6—C10.4 (4)C18—C17—C26—O6179.25 (18)
C1—C7—C8—C9177.9 (2)N1—C19—C20—C166.2 (2)
C7—C8—C9—O13.8 (4)N1—C19—C20—C21177.00 (17)
C7—C8—C9—O2176.4 (2)C24—C19—C20—C16173.42 (17)
O2—C10—C11—C12176.5 (2)C24—C19—C20—C213.4 (3)
C15—C10—C11—C120.1 (4)C16—C20—C21—O39.3 (3)
O2—C10—C15—C14177.68 (18)C16—C20—C21—O4170.37 (15)
C11—C10—C15—C141.4 (3)C19—C20—C21—O3173.65 (19)
C10—C11—C12—C131.8 (4)C19—C20—C21—O46.7 (3)
C11—C12—C13—C142.1 (3)
Symmetry code: (i) x, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.87 (2)2.31 (2)3.148 (2)163 (2)
O1W—H1W···O51.041.812.615 (6)132
C14—H14···O1Wii0.932.503.140 (6)126
Symmetry codes: (i) x, y, z+1/2; (ii) x, y1, z+1/2.

Experimental details

Crystal data
Chemical formulaC28H29NO6·0.5H2O
Mr484.53
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)25.4905 (11), 8.6166 (4), 23.2902 (10)
β (°) 92.235 (2)
V3)5111.6 (4)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.25 × 0.20 × 0.20
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker 2004)
Tmin, Tmax0.979, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections
24059, 5036, 3271
Rint0.027
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.146, 1.09
No. of reflections5036
No. of parameters344
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.867 (15)2.308 (16)3.148 (2)163.4 (18)
O1W—H1W···O51.041.812.615 (6)132
C14—H14···O1Wii0.932.503.140 (6)126
Symmetry codes: (i) x, y, z+1/2; (ii) x, y1, z+1/2.
 

Acknowledgements

SA thanks the UGC, India, for financial support

References

First citationAnadu, N. O., Davisson, V. J. & Cushman, M. (2006). J. Med. Chem. 49, 3897–3905.  Web of Science CrossRef PubMed CAS
First citationBartzatt, R., Cirillo, S. L. & Cirillo, J. D. (2004). Physiol. Chem. Phys. Med. NMR, 36, 85–94.  PubMed CAS
First citationBi, Y., Xu, J., Sun, F., Wu, X., Ye, W., Sun, Y. & Huang, W. (2012). Molecules, 17, 8832–8841.  Web of Science CrossRef CAS PubMed
First citationBruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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