Diethyl 2,6-dimethyl-4-[4-(3-phenyl­acrylo­yloxy)phen­yl]-1,4-dihydro­pyridine-3,5-dicarboxyl­ate hemihydrate

Sharmila, P.; Suresh Kumar, C.; Ananth, K.; Narasimhan, S.; Aravindhan, S.

doi:10.1107/S1600536813004108

organic compounds

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ISSN: 2056-9890

Volume 69| Part 3| March 2013| Page o389

doi:10.1107/S1600536813004108

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Diethyl 2,6-dimethyl-4-[4-(3-phenylacryloyloxy)phenyl]-1,4-dihydropyridine-3,5-dicarboxylate hemihydrate

P. Sharmila,^a C. Suresh Kumar,^b Karthik Ananth,^b S. Narasimhan ^b and S. Aravindhan ^a ^*

^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 ); Bartzatt et al. (2004 ); Anadu et al. (2006 ).

Experimental

Crystal data

C₂₈H₂₉NO₆·0.5H₂O
M_r = 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 ) T_min = 0.979, T_max = 0.983
24059 measured reflections
5036 independent reflections
3271 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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) $[-x, y, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y-1, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813004108/su2546sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813004108/su2546Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813004108/su2546Isup3.cml

checkCIF report

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.

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

	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].
	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

C₂₈H₂₉NO₆·0.5H₂O	F(000) = 2056
M_r = 484.53	D_x = 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

Data collection top

Bruker Kappa APEXII CCD diffractometer	5036 independent reflections
Radiation source: fine-focus sealed tube	3271 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω and ϕ scan	θ_max = 26.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker 2004)	h = −31→21
T_min = 0.979, T_max = 0.983	k = −10→10
24059 measured reflections	l = −28→27

Refinement top

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(F_o²) + (0.0654P)² + 1.6916P] where P = (F_o² + 2F_c²)/3
5036 reflections	(Δ/σ)_max = 0.008
344 parameters	Δρ_max = 0.18 e Å⁻³
2 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₈H₂₉NO₆·0.5H₂O	V = 5111.6 (4) Å³
M_r = 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)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	5036 independent reflections
Absorption correction: multi-scan (SADABS; Bruker 2004)	3271 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.983	R_int = 0.027
24059 measured reflections

Refinement top

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	Δρ_max = 0.18 e Å⁻³
5036 reflections	Δρ_min = −0.31 e Å⁻³
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

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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.

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.979, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	24059, 5036, 3271
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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
Bartzatt, R., Cirillo, S. L. & Cirillo, J. D. (2004). Physiol. Chem. Phys. Med. NMR, 36, 85–94. PubMed CAS Google Scholar
Bi, Y., Xu, J., Sun, F., Wu, X., Ye, W., Sun, Y. & Huang, W. (2012). Molecules, 17, 8832–8841. Web of Science CrossRef CAS PubMed Google Scholar
Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 69| Part 3| March 2013| Page o389

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

Di­ethyl 2,6-di­methyl-4-[4-(3-phenyl­acrylo­yl­oxy)phen­yl]-1,4-di­hydro­pyridine-3,5-di­carboxyl­ate hemihydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Diethyl 2,6-dimethyl-4-[4-(3-phenylacryloyloxy)phenyl]-1,4-dihydropyridine-3,5-dicarboxylate hemihydrate