Ethyl 4-hydr­oxy-1-(2-morpholinopro­pano­yl)-2,6-diphenyl-1,2,5,6-tetra­hydro­pyridin-3-carboxyl­ate

Aridoss, G.; Gayathri, D.; Ramachandran, R.; Lim, K.T.; Jeong, Y.T.

doi:10.1107/S1600536809050259

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages o3232-o3233

doi:10.1107/S1600536809050259

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Ethyl 4-hydroxy-1-(2-morpholinopropanoyl)-2,6-diphenyl-1,2,5,6-tetrahydropyridin-3-carboxylate

G. Aridoss,^a D. Gayathri,^b R. Ramachandran,^c Kwon Taek Lim ^a and Yeon Tae Jeong ^a ^*

^aDivision of Image Science and Information Engineering, Pukyong National University, Busan 608-739, Republic of Korea, ^bInstitute of Structural Biology and Biophysics-2: Molecular Biophysics, Research Centre Jülich, D-52425 Jülich, Germany, and ^cDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, India
^*Correspondence e-mail: ytjeong@pknu.ac.kr

(Received 18 November 2009; accepted 23 November 2009; online 28 November 2009)

In the title compound, C₂₇H₃₂N₂O₅, the morpholine ring adopts a chair conformation with two C atoms deviating by −0.656 (4) and 0.679 (3) Å from the least-squares plane defined by the rest of atoms in the ring. The tetrahydropyridine ring adopts a half-chair conformation. The molecular structure is stabilized by a strong intramolecular O—H⋯O interaction, generating an S(6) motif. The crystal packing is stabilized by intermolecular C—H⋯O interactions, generating a C(7) chain along the a axis, and R₂²(20) and R₄⁴(20) graph-set motifs.

Related literature

For related structures, see: Aridoss et al. (2009a ,b ); Gayathri et al. (2008 ); Kavitha et al. (2007 ); Ramachandran et al. (2008 ); Subha Nandhini et al. (2003 ). For ring conformational analysis, see: Cremer & Pople (1975 ); Nardelli (1983 ).

Experimental

Crystal data

C₂₇H₃₂N₂O₅
M_r = 464.55
Monoclinic, P 2₁ /c
a = 8.2251 (2) Å
b = 10.6219 (4) Å
c = 28.7046 (10) Å
β = 92.375 (2)°
V = 2505.66 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker 1999 ) T_min = 0.975, T_max = 0.983
22895 measured reflections
4850 independent reflections
3353 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.145
S = 1.02
4850 reflections
308 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O4	0.82	1.83	2.542 (2)	145
C10—H10A⋯O1ⁱ	0.97	2.51	3.311 (3)	140
C11—H11A⋯O2ⁱⁱ	0.97	2.54	3.222 (3)	127
C26—H26B⋯O3ⁱⁱⁱ	0.97	2.53	3.470 (4)	163
Symmetry codes: (i) x+1, y, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x-1, y, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809050259/is2497sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809050259/is2497Isup2.hkl

checkCIF report

Comment top

It has been reported earlier that 2,6-diarylpiperidin-4-ones are in rigid chair conformation with equatorial orientation of the two aryl groups (Gayathri et al. 2008; Kavitha et al. 2007). Upon chloroacetylation (Aridoss et al. 2009b) or bromoacetylation (Ramachandran et al. 2008) of the 2,6-diarylpiperidin-4-one, the normal chair conformation of the piperidone ring was changed into non-chair conformation of its preference. Similarly, bromopropionylation of ethyl 4-oxo-2,6-diphenyl-4-piperidin-3-carboxylate gave ethyl 1-(2-bromopropanoyl)-4-hydroxy-2,6-diphenyl- 1,2,5,6-tetrahydropyridin-3-carboxylate as the product (Aridoss et al. 2009a) wherein the normal chair conformation of the piperidone ring in starting material (Subha Nandhini et al. 2003) was changed into a non-chair conformation. In continuation of this, we report here the crystal structure of the title compound.

The sum of the angles at N1 [359.5 (6)°] and N2 [337.6 (6)°] are in accordance with sp² and sp³ hybridization. The dihedral angle between the two phenyl rings is 35.0 (1)°. The morpholine ring adopts a chair conformation with atoms C9 and C11 deviating by -0.656 (4) and 0.679 (3) Å, respectively, from the least squares plane defined by N2/C8/O2/C10. The tetrahydropyridine ring adopts a half chair conformation. The puckering parameters (Cremer & Pople, 1975) and the smallest displacement asymmetry parameters (Nardelli, 1983) for the morpholine and tetrahydropyridine rings are q₂ = 0.010 (3), 0.324 (2) Å, q₃ = -0.572 (3), -0.287 (2) Å; Q_T = 0.573 (3), 0.433 (2) Å and θ = 177.8 (3), 131.5 (3)°, respectively.

The molecule is stabilized by a strong O—H···O intramolecular interaction, wherein, atom O3 acts as a donor to O4, generating an S(6) motif. The crystal packing is stabilized by C—H···O intermolecular interactions. Atoms C10 and C26 act as donors to O1 and O3, respectively, each generating a chain of C(7) running along the a axis, which in turn generates an R₂²(20) graph set motif. Atom C11 acts as a donor to O2 at (1 - x, 1/2 + y, 1/2 - z), generating an R₄⁴(20) graph set motif together with a C10—H10A···O1 intermolecular interaction.

Related literature top

For related structures, see: Aridoss et al. (2009a,b); Gayathri et al. (2008); Kavitha et al. (2007); Ramachandran et al. (2008); Subha Nandhini et al. (2003). For ring conformational analysis, see: Cremer & Pople (1975); Nardelli (1983).

Experimental top

To a solution of morpholine (1 equiv.) and dry K₂CO₃ in benzene, ethyl 1-(2-bromopropanoyl)-4-hydroxy-2,6-diphenyl-1,2,5,6-tetrahydropyridin-3- carboxylate (1 equiv.) in benzene (Aridoss et al., 2009a) was added slowly over a period of 15 minutes. Later the contents were refluxed over night. After the completion of reaction, the contents were poured into water and extracted twice with ethyl acetate. The combined organic extracts were then washed well with brine and dried over anhydrous sodium sulfate. This upon evaporation, column purification and subsequent recrystallization in distilled ethanol afforded fine white crystals suitable for X-ray diffraction study.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The molecular packing of (I). For clarity, hydrogen atoms which are not involved in hydrogen bonding are omitted.

Ethyl 4-hydroxy-1-(2-morpholinopropanoyl)-2,6-diphenyl- 1,2,5,6-tetrahydropyridin-3-carboxylate top

Crystal data top

C₂₇H₃₂N₂O₅	F(000) = 992
M_r = 464.55	D_x = 1.231 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5113 reflections
a = 8.2251 (2) Å	θ = 2.4–23.3°
b = 10.6219 (4) Å	µ = 0.09 mm⁻¹
c = 28.7046 (10) Å	T = 293 K
β = 92.375 (2)°	Block, colourless
V = 2505.66 (14) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	4850 independent reflections
Radiation source: fine-focus sealed tube	3353 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω and ϕ scan	θ_max = 25.9°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker 1999)	h = −10→9
T_min = 0.975, T_max = 0.983	k = −13→12
22895 measured reflections	l = −35→35

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.145	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0554P)² + 1.1339P] where P = (F_o² + 2F_c²)/3
4850 reflections	(Δ/σ)_max < 0.001
308 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₇H₃₂N₂O₅	V = 2505.66 (14) Å³
M_r = 464.55	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.2251 (2) Å	µ = 0.09 mm⁻¹
b = 10.6219 (4) Å	T = 293 K
c = 28.7046 (10) Å	0.30 × 0.20 × 0.20 mm
β = 92.375 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4850 independent reflections
Absorption correction: multi-scan (SADABS; Bruker 1999)	3353 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.983	R_int = 0.036
22895 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.145	H-atom parameters constrained
S = 1.02	Δρ_max = 0.29 e Å⁻³
4850 reflections	Δρ_min = −0.21 e Å⁻³
308 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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
O1	−0.09176 (19)	0.60293 (18)	0.27695 (5)	0.0644 (5)
N2	0.2969 (2)	0.54061 (17)	0.28207 (6)	0.0498 (5)
C1	0.2028 (2)	0.6983 (2)	0.36715 (7)	0.0444 (5)
H1A	0.2803	0.7179	0.3432	0.053*
C2	0.2787 (3)	0.5948 (2)	0.39704 (8)	0.0509 (5)
H2A	0.3412	0.5401	0.3775	0.061*
H2B	0.3535	0.6323	0.4201	0.061*
O2	0.4987 (2)	0.32639 (18)	0.27766 (9)	0.0972 (7)
O3	0.2277 (2)	0.44389 (18)	0.45418 (6)	0.0688 (5)
H3A	0.1594	0.3950	0.4637	0.118 (15)*
C3	0.1586 (3)	0.5184 (2)	0.42121 (7)	0.0502 (5)
O4	−0.0581 (2)	0.36103 (18)	0.46520 (6)	0.0758 (5)
C4	−0.0018 (3)	0.5187 (2)	0.40991 (7)	0.0491 (5)
O5	−0.2586 (2)	0.43166 (18)	0.41704 (7)	0.0763 (5)
C5	−0.0748 (2)	0.6014 (2)	0.37157 (7)	0.0445 (5)
H5A	−0.1409	0.5455	0.3513	0.053*
N1	0.05448 (19)	0.65010 (16)	0.34259 (5)	0.0433 (4)
C6	0.0380 (3)	0.6339 (2)	0.29554 (7)	0.0486 (5)
C7	0.1903 (3)	0.6443 (2)	0.26673 (7)	0.0509 (5)
H7A	0.2453	0.7233	0.2753	0.061*
C8	0.2302 (3)	0.4162 (2)	0.27172 (10)	0.0669 (7)
H8A	0.2218	0.4036	0.2382	0.080*
H8B	0.1219	0.4096	0.2837	0.080*
C9	0.3375 (3)	0.3183 (3)	0.29354 (13)	0.0853 (9)
H9A	0.3400	0.3282	0.3272	0.102*
H9B	0.2933	0.2356	0.2861	0.102*
C10	0.5629 (3)	0.4474 (3)	0.28766 (12)	0.0811 (9)
H10A	0.6724	0.4527	0.2765	0.097*
H10B	0.5690	0.4600	0.3212	0.097*
C11	0.4610 (3)	0.5486 (2)	0.26541 (9)	0.0634 (7)
H11A	0.5074	0.6303	0.2731	0.076*
H11B	0.4584	0.5390	0.2318	0.076*
C12	−0.1901 (2)	0.7031 (2)	0.38781 (7)	0.0454 (5)
C13	−0.2138 (3)	0.7287 (3)	0.43393 (8)	0.0654 (7)
H13A	−0.1534	0.6855	0.4569	0.078*
C14	−0.3262 (3)	0.8179 (3)	0.44672 (11)	0.0777 (8)
H14A	−0.3411	0.8335	0.4781	0.093*
C15	−0.4147 (3)	0.8827 (3)	0.41383 (12)	0.0761 (8)
H15A	−0.4900	0.9427	0.4225	0.091*
C16	−0.3922 (3)	0.8588 (3)	0.36786 (12)	0.0791 (8)
H16A	−0.4518	0.9034	0.3451	0.095*
C17	−0.2821 (3)	0.7691 (3)	0.35491 (9)	0.0647 (7)
H17A	−0.2696	0.7528	0.3234	0.078*
C18	0.1703 (2)	0.8208 (2)	0.39239 (7)	0.0456 (5)
C19	0.1431 (3)	0.9284 (2)	0.36661 (9)	0.0683 (7)
H19A	0.1400	0.9239	0.3342	0.082*
C20	0.1205 (4)	1.0428 (3)	0.38800 (12)	0.0894 (10)
H20A	0.1021	1.1148	0.3701	0.107*
C21	0.1254 (4)	1.0502 (3)	0.43555 (12)	0.0841 (9)
H21A	0.1099	1.1274	0.4500	0.101*
C22	0.1524 (3)	0.9460 (3)	0.46159 (9)	0.0727 (8)
H22A	0.1563	0.9515	0.4940	0.087*
C23	0.1744 (3)	0.8312 (2)	0.44022 (8)	0.0577 (6)
H23A	0.1923	0.7598	0.4584	0.069*
C24	0.1449 (3)	0.6501 (3)	0.21484 (8)	0.0750 (8)
H24A	0.2419	0.6567	0.1976	0.113*
H24B	0.0771	0.7222	0.2086	0.113*
H24C	0.0870	0.5750	0.2057	0.113*
C25	−0.1051 (3)	0.4311 (2)	0.43333 (9)	0.0593 (6)
C26	−0.3741 (4)	0.3489 (3)	0.43944 (13)	0.0938 (10)
H26A	−0.3403	0.3369	0.4719	0.113*
H26B	−0.4810	0.3875	0.4383	0.113*
C27	−0.3819 (6)	0.2296 (4)	0.41630 (19)	0.1500 (18)
H27A	−0.4578	0.1761	0.4313	0.225*
H27B	−0.2762	0.1912	0.4177	0.225*
H27C	−0.4169	0.2416	0.3843	0.225*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0516 (9)	0.0898 (13)	0.0509 (9)	−0.0112 (9)	−0.0078 (7)	−0.0060 (8)
N2	0.0478 (10)	0.0492 (11)	0.0528 (10)	−0.0081 (8)	0.0058 (8)	−0.0110 (8)
C1	0.0400 (11)	0.0524 (13)	0.0408 (10)	−0.0027 (9)	0.0002 (8)	−0.0027 (9)
C2	0.0457 (12)	0.0547 (13)	0.0518 (12)	0.0047 (10)	−0.0029 (9)	−0.0057 (10)
O2	0.0619 (12)	0.0616 (12)	0.169 (2)	0.0010 (9)	0.0195 (12)	−0.0312 (13)
O3	0.0628 (10)	0.0734 (12)	0.0696 (11)	0.0181 (10)	−0.0053 (9)	0.0206 (9)
C3	0.0548 (13)	0.0490 (13)	0.0466 (12)	0.0115 (10)	−0.0001 (10)	−0.0004 (10)
O4	0.0742 (12)	0.0752 (12)	0.0780 (12)	0.0057 (10)	0.0046 (9)	0.0336 (10)
C4	0.0472 (12)	0.0507 (13)	0.0493 (12)	0.0049 (10)	0.0022 (9)	0.0051 (10)
O5	0.0573 (10)	0.0811 (13)	0.0902 (13)	−0.0100 (9)	0.0009 (9)	0.0335 (10)
C5	0.0411 (11)	0.0482 (12)	0.0438 (11)	−0.0037 (9)	−0.0013 (9)	0.0040 (9)
N1	0.0397 (9)	0.0502 (10)	0.0399 (9)	−0.0025 (8)	−0.0006 (7)	−0.0016 (8)
C6	0.0494 (12)	0.0520 (13)	0.0439 (11)	−0.0026 (10)	−0.0020 (9)	−0.0026 (10)
C7	0.0557 (13)	0.0551 (14)	0.0420 (11)	−0.0060 (11)	0.0029 (9)	−0.0028 (10)
C8	0.0549 (14)	0.0582 (15)	0.0883 (18)	−0.0127 (12)	0.0102 (13)	−0.0190 (14)
C9	0.0709 (18)	0.0493 (16)	0.137 (3)	−0.0089 (13)	0.0176 (18)	−0.0140 (17)
C10	0.0524 (15)	0.0664 (18)	0.125 (3)	−0.0077 (13)	0.0122 (15)	−0.0193 (17)
C11	0.0523 (13)	0.0639 (16)	0.0748 (16)	−0.0151 (12)	0.0146 (12)	−0.0146 (13)
C12	0.0364 (10)	0.0493 (12)	0.0505 (12)	−0.0039 (9)	0.0012 (9)	0.0070 (10)
C13	0.0607 (14)	0.0823 (18)	0.0530 (13)	0.0145 (13)	−0.0005 (11)	−0.0028 (13)
C14	0.0641 (16)	0.093 (2)	0.0767 (18)	0.0074 (16)	0.0106 (14)	−0.0208 (16)
C15	0.0513 (15)	0.0607 (17)	0.117 (3)	0.0051 (12)	0.0178 (15)	−0.0037 (17)
C16	0.0612 (16)	0.078 (2)	0.099 (2)	0.0209 (14)	0.0122 (15)	0.0306 (17)
C17	0.0573 (14)	0.0737 (17)	0.0636 (15)	0.0108 (13)	0.0070 (11)	0.0185 (13)
C18	0.0378 (11)	0.0509 (13)	0.0476 (12)	−0.0014 (9)	−0.0027 (9)	−0.0040 (10)
C19	0.0879 (19)	0.0577 (16)	0.0577 (14)	0.0038 (13)	−0.0153 (13)	−0.0019 (12)
C20	0.118 (3)	0.0547 (17)	0.093 (2)	0.0152 (16)	−0.0289 (19)	−0.0008 (16)
C21	0.091 (2)	0.0642 (19)	0.095 (2)	0.0138 (16)	−0.0131 (17)	−0.0268 (17)
C22	0.0827 (19)	0.075 (2)	0.0602 (15)	0.0021 (15)	0.0043 (13)	−0.0204 (15)
C23	0.0636 (14)	0.0596 (15)	0.0502 (13)	−0.0008 (12)	0.0064 (11)	−0.0055 (11)
C24	0.0797 (18)	0.101 (2)	0.0441 (13)	−0.0055 (16)	0.0046 (12)	0.0004 (14)
C25	0.0559 (14)	0.0597 (15)	0.0625 (14)	0.0066 (12)	0.0047 (11)	0.0135 (12)
C26	0.0666 (18)	0.096 (3)	0.119 (3)	−0.0084 (17)	0.0110 (17)	0.041 (2)
C27	0.161 (4)	0.083 (3)	0.206 (5)	−0.035 (3)	0.016 (4)	0.014 (3)

Geometric parameters (Å, º) top

O1—C6	1.219 (2)	C10—H10B	0.9700
N2—C11	1.453 (3)	C11—H11A	0.9700
N2—C8	1.457 (3)	C11—H11B	0.9700
N2—C7	1.464 (3)	C12—C13	1.373 (3)
C1—N1	1.475 (2)	C12—C17	1.377 (3)
C1—C2	1.513 (3)	C13—C14	1.384 (4)
C1—C18	1.518 (3)	C13—H13A	0.9300
C1—H1A	0.9800	C14—C15	1.356 (4)
C2—C3	1.474 (3)	C14—H14A	0.9300
C2—H2A	0.9700	C15—C16	1.364 (4)
C2—H2B	0.9700	C15—H15A	0.9300
O2—C10	1.414 (3)	C16—C17	1.376 (4)
O2—C9	1.423 (3)	C16—H16A	0.9300
O3—C3	1.342 (3)	C17—H17A	0.9300
O3—H3A	0.8200	C18—C19	1.375 (3)
C3—C4	1.345 (3)	C18—C23	1.376 (3)
O4—C25	1.229 (3)	C19—C20	1.378 (4)
C4—C25	1.445 (3)	C19—H19A	0.9300
C4—C5	1.513 (3)	C20—C21	1.366 (4)
O5—C25	1.328 (3)	C20—H20A	0.9300
O5—C26	1.463 (3)	C21—C22	1.349 (4)
C5—N1	1.471 (2)	C21—H21A	0.9300
C5—C12	1.524 (3)	C22—C23	1.380 (3)
C5—H5A	0.9800	C22—H22A	0.9300
N1—C6	1.363 (3)	C23—H23A	0.9300
C6—C7	1.533 (3)	C24—H24A	0.9600
C7—C24	1.522 (3)	C24—H24B	0.9600
C7—H7A	0.9800	C24—H24C	0.9600
C8—C9	1.486 (4)	C26—C27	1.430 (5)
C8—H8A	0.9700	C26—H26A	0.9700
C8—H8B	0.9700	C26—H26B	0.9700
C9—H9A	0.9700	C27—H27A	0.9600
C9—H9B	0.9700	C27—H27B	0.9600
C10—C11	1.491 (4)	C27—H27C	0.9600
C10—H10A	0.9700

C11—N2—C8	109.46 (18)	C10—C11—H11A	109.8
C11—N2—C7	114.22 (18)	N2—C11—H11B	109.8
C8—N2—C7	113.89 (18)	C10—C11—H11B	109.8
N1—C1—C2	109.42 (17)	H11A—C11—H11B	108.3
N1—C1—C18	111.54 (16)	C13—C12—C17	117.7 (2)
C2—C1—C18	115.37 (17)	C13—C12—C5	123.4 (2)
N1—C1—H1A	106.7	C17—C12—C5	118.8 (2)
C2—C1—H1A	106.7	C12—C13—C14	120.9 (2)
C18—C1—H1A	106.7	C12—C13—H13A	119.5
C3—C2—C1	113.42 (17)	C14—C13—H13A	119.5
C3—C2—H2A	108.9	C15—C14—C13	120.6 (3)
C1—C2—H2A	108.9	C15—C14—H14A	119.7
C3—C2—H2B	108.9	C13—C14—H14A	119.7
C1—C2—H2B	108.9	C14—C15—C16	119.3 (3)
H2A—C2—H2B	107.7	C14—C15—H15A	120.4
C10—O2—C9	109.6 (2)	C16—C15—H15A	120.4
C3—O3—H3A	109.5	C15—C16—C17	120.5 (3)
O3—C3—C4	123.6 (2)	C15—C16—H16A	119.8
O3—C3—C2	112.59 (19)	C17—C16—H16A	119.8
C4—C3—C2	123.7 (2)	C12—C17—C16	121.1 (2)
C3—C4—C25	118.4 (2)	C12—C17—H17A	119.5
C3—C4—C5	122.17 (19)	C16—C17—H17A	119.5
C25—C4—C5	119.27 (19)	C19—C18—C23	117.8 (2)
C25—O5—C26	117.9 (2)	C19—C18—C1	118.91 (19)
N1—C5—C4	109.94 (16)	C23—C18—C1	123.2 (2)
N1—C5—C12	113.43 (17)	C18—C19—C20	121.0 (2)
C4—C5—C12	114.99 (17)	C18—C19—H19A	119.5
N1—C5—H5A	105.9	C20—C19—H19A	119.5
C4—C5—H5A	105.9	C21—C20—C19	119.8 (3)
C12—C5—H5A	105.9	C21—C20—H20A	120.1
C6—N1—C5	118.14 (16)	C19—C20—H20A	120.1
C6—N1—C1	124.31 (17)	C22—C21—C20	120.2 (3)
C5—N1—C1	117.05 (15)	C22—C21—H21A	119.9
O1—C6—N1	121.15 (19)	C20—C21—H21A	119.9
O1—C6—C7	120.23 (19)	C21—C22—C23	120.0 (3)
N1—C6—C7	118.41 (18)	C21—C22—H22A	120.0
N2—C7—C24	116.4 (2)	C23—C22—H22A	120.0
N2—C7—C6	106.06 (17)	C18—C23—C22	121.1 (2)
C24—C7—C6	110.97 (18)	C18—C23—H23A	119.5
N2—C7—H7A	107.7	C22—C23—H23A	119.5
C24—C7—H7A	107.7	C7—C24—H24A	109.5
C6—C7—H7A	107.7	C7—C24—H24B	109.5
N2—C8—C9	109.7 (2)	H24A—C24—H24B	109.5
N2—C8—H8A	109.7	C7—C24—H24C	109.5
C9—C8—H8A	109.7	H24A—C24—H24C	109.5
N2—C8—H8B	109.7	H24B—C24—H24C	109.5
C9—C8—H8B	109.7	O4—C25—O5	122.0 (2)
H8A—C8—H8B	108.2	O4—C25—C4	124.3 (2)
O2—C9—C8	111.6 (2)	O5—C25—C4	113.7 (2)
O2—C9—H9A	109.3	C27—C26—O5	110.2 (3)
C8—C9—H9A	109.3	C27—C26—H26A	109.6
O2—C9—H9B	109.3	O5—C26—H26A	109.6
C8—C9—H9B	109.3	C27—C26—H26B	109.6
H9A—C9—H9B	108.0	O5—C26—H26B	109.6
O2—C10—C11	111.7 (2)	H26A—C26—H26B	108.1
O2—C10—H10A	109.3	C26—C27—H27A	109.5
C11—C10—H10A	109.3	C26—C27—H27B	109.5
O2—C10—H10B	109.3	H27A—C27—H27B	109.5
C11—C10—H10B	109.3	C26—C27—H27C	109.5
H10A—C10—H10B	107.9	H27A—C27—H27C	109.5
N2—C11—C10	109.3 (2)	H27B—C27—H27C	109.5
N2—C11—H11A	109.8

N1—C1—C2—C3	−40.7 (2)	C9—O2—C10—C11	−58.4 (3)
C18—C1—C2—C3	86.0 (2)	C8—N2—C11—C10	−57.6 (3)
C1—C2—C3—O3	−167.93 (18)	C7—N2—C11—C10	173.3 (2)
C1—C2—C3—C4	15.2 (3)	O2—C10—C11—N2	58.9 (3)
O3—C3—C4—C25	−2.2 (3)	N1—C5—C12—C13	−120.7 (2)
C2—C3—C4—C25	174.4 (2)	C4—C5—C12—C13	7.0 (3)
O3—C3—C4—C5	−178.2 (2)	N1—C5—C12—C17	62.6 (3)
C2—C3—C4—C5	−1.6 (3)	C4—C5—C12—C17	−169.6 (2)
C3—C4—C5—N1	14.9 (3)	C17—C12—C13—C14	0.0 (4)
C25—C4—C5—N1	−161.11 (19)	C5—C12—C13—C14	−176.7 (2)
C3—C4—C5—C12	−114.6 (2)	C12—C13—C14—C15	−0.5 (4)
C25—C4—C5—C12	69.4 (3)	C13—C14—C15—C16	0.2 (4)
C4—C5—N1—C6	127.7 (2)	C14—C15—C16—C17	0.6 (4)
C12—C5—N1—C6	−102.0 (2)	C13—C12—C17—C16	0.9 (4)
C4—C5—N1—C1	−44.5 (2)	C5—C12—C17—C16	177.7 (2)
C12—C5—N1—C1	85.8 (2)	C15—C16—C17—C12	−1.2 (4)
C2—C1—N1—C6	−113.0 (2)	N1—C1—C18—C19	−71.5 (2)
C18—C1—N1—C6	118.1 (2)	C2—C1—C18—C19	162.9 (2)
C2—C1—N1—C5	58.7 (2)	N1—C1—C18—C23	111.8 (2)
C18—C1—N1—C5	−70.1 (2)	C2—C1—C18—C23	−13.8 (3)
C5—N1—C6—O1	14.1 (3)	C23—C18—C19—C20	−0.1 (4)
C1—N1—C6—O1	−174.3 (2)	C1—C18—C19—C20	−177.0 (3)
C5—N1—C6—C7	−160.63 (18)	C18—C19—C20—C21	0.2 (5)
C1—N1—C6—C7	11.0 (3)	C19—C20—C21—C22	0.1 (5)
C11—N2—C7—C24	67.5 (3)	C20—C21—C22—C23	−0.4 (5)
C8—N2—C7—C24	−59.3 (3)	C19—C18—C23—C22	−0.1 (3)
C11—N2—C7—C6	−168.57 (18)	C1—C18—C23—C22	176.6 (2)
C8—N2—C7—C6	64.6 (2)	C21—C22—C23—C18	0.4 (4)
O1—C6—C7—N2	−110.6 (2)	C26—O5—C25—O4	2.3 (4)
N1—C6—C7—N2	64.2 (2)	C26—O5—C25—C4	−178.2 (2)
O1—C6—C7—C24	16.7 (3)	C3—C4—C25—O4	4.8 (4)
N1—C6—C7—C24	−168.6 (2)	C5—C4—C25—O4	−179.1 (2)
C11—N2—C8—C9	57.5 (3)	C3—C4—C25—O5	−174.8 (2)
C7—N2—C8—C9	−173.2 (2)	C5—C4—C25—O5	1.4 (3)
C10—O2—C9—C8	58.0 (3)	C25—O5—C26—C27	−91.5 (4)
N2—C8—C9—O2	−58.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O4	0.82	1.83	2.542 (2)	145
C10—H10A···O1ⁱ	0.97	2.51	3.311 (3)	140
C11—H11A···O2ⁱⁱ	0.97	2.54	3.222 (3)	127
C26—H26B···O3ⁱⁱⁱ	0.97	2.53	3.470 (4)	163

Symmetry codes: (i) x+1, y, z; (ii) −x+1, y+1/2, −z+1/2; (iii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₇H₃₂N₂O₅
M_r	464.55
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.2251 (2), 10.6219 (4), 28.7046 (10)
β (°)	92.375 (2)
V (Å³)	2505.66 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker 1999)
T_min, T_max	0.975, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	22895, 4850, 3353
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.615

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.145, 1.02
No. of reflections	4850
No. of parameters	308
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.21

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O4	0.82	1.83	2.542 (2)	145
C10—H10A···O1ⁱ	0.97	2.51	3.311 (3)	140
C11—H11A···O2ⁱⁱ	0.97	2.54	3.222 (3)	127
C26—H26B···O3ⁱⁱⁱ	0.97	2.53	3.470 (4)	163

Symmetry codes: (i) x+1, y, z; (ii) −x+1, y+1/2, −z+1/2; (iii) x−1, y, z.

Acknowledgements

GA and YTJ acknowledge the support provided by the second stage of the BK21 program, Republic of Korea.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals Google Scholar
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Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
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Nardelli, M. (1983). Acta Cryst. C39, 1141–1142. CrossRef CAS Web of Science IUCr Journals Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Subha Nandhini, M., Vijayakumar, V., Mostad, A., Sundaravadivelu, M. & Natarajan, S. (2003). Acta Cryst. E59, o1672–o1674. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 65| Part 12| December 2009| Pages o3232-o3233

doi:10.1107/S1600536809050259

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

Ethyl 4-hydr­­oxy-1-(2-morpholinopro­pano­yl)-2,6-di­phenyl-1,2,5,6-tetra­hydro­pyridin-3-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethyl 4-hydroxy-1-(2-morpholinopropanoyl)-2,6-diphenyl-1,2,5,6-tetrahydropyridin-3-carboxylate