Ethyl 4-hydr­oxy-2,6-diphenyl-1-(2-thio­morpholinopropano­yl)-1,2,5,6-tetra­hydro­pyridine-3-carboxyl­ate

Aridoss, G.; Gayathri, D.; Park, K.S.; Kim, J.T.; Jeong, Y.T.

doi:10.1107/S1600536809049186

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages o3180-o3181

doi:10.1107/S1600536809049186

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Ethyl 4-hydroxy-2,6-diphenyl-1-(2-thiomorpholinopropanoyl)-1,2,5,6-tetrahydropyridine-3-carboxylate

G. Aridoss,^a D. Gayathri,^b Keun Soo Park,^a Jong Tae Kim ^a and Yeon Tae Jeong ^a ^*

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

(Received 14 November 2009; accepted 18 November 2009; online 21 November 2009)

In the title compound, C₂₇H₃₂N₂O₄S, the thiomorpholine ring adopts a chair conformation and the tetrahydropyridine ring is in a distorted envelope conformation. The molecular structure is stabilized by an intramolecular O—H⋯O interaction and the crystal packing is stabilized by an intermolecular C—H⋯O interaction, generating an S(6) motif and a dimer of the type R₂²(18), respectively.

Related literature

For the synthesis and biological activity of 2,6-diarylpiperidin-4-one derivatives, see: Aridoss, Balasubramanian, Parthiban, Ramachandran & Kabilan (2007 ); Aridoss, Balasubramanian, Parthiban & Kabilan (2007 ); Aridoss, Parthiban et al. (2009 ). For a related structure, see: Aridoss, Gayathri et al. (2009 ). For ring conformational analysis, see: Cremer & Pople (1975 ); Nardelli (1983 ).

Experimental

Crystal data

C₂₇H₃₂N₂O₄S
M_r = 480.61
Triclinic, $[P \overline 1]$
a = 9.904 (3) Å
b = 11.400 (4) Å
c = 12.103 (4) Å
α = 93.908 (18)°
β = 104.941 (15)°
γ = 106.819 (16)°
V = 1248.7 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ) T_min = 0.952, T_max = 0.968
26182 measured reflections
5707 independent reflections
4543 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.117
S = 1.01
5707 reflections
309 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3	0.82	1.85	2.560 (2)	144
C24—H24B⋯O3ⁱ	0.96	2.54	3.285 (2)	135
Symmetry code: (i) -x+2, -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., 1994 ); 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/S1600536809049186/is2490sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809049186/is2490Isup2.hkl

checkCIF report

Comment top

Our current research work is committed to find 2,6-diarylpiperidin-4-one based lead drug for the antimicrobial therapy and exploring the stereochemistry of its N-acyl derivatives (Aridoss, Balasubramanian, Parthiban, Ramachandran & Kabilan, 2007; Aridoss, Balasubramanian, Parthiban & Kabilan, 2007; Aridoss, Parthiban et al., 2009). Recently we have disclosed the crystal structure of ethyl 1-(2-bromopropanoyl)-4-hydroxy-2,6-diphenyl-1,2,5,6- tetrahydropyridin-3-carboxylate (Aridoss, Gayathri et al., 2009), which crystallizes with two independent molecules per asymmetric unit. Here, the tetrahydropyridine ring adopts a half-chair conformation in one molecule and distorted envelope conformation in other molecule. Thus to understand the change in conformation of the above said compound upon nucleophilic substitution of thiomorpholine in place of bromine, crystal structure of the title compound is determined by X-ray diffraction study and discussed in this paper.

The sum of the angles at N1 [358.6 (3)°] and N2 [336.1 (3)°] are in accordance with sp² and sp³ hybridization, respectively. The dihedral angle between the two phenyl rings attached to the pyridine moiety is 21.8 (1)°. The thiomorpholine ring adopts chair conformation with atoms C9 and C11 deviating by 0.758 (2) and -0.673 (2) Å, respectively, from the least squares plane defined by atoms N2/C8/S1/C10. The tetrahydropyridine ring adops distorted envelope conformation. The puckering parameters (Cremer & Pople, 1975) and the smallest displacement asymmetry parameters (Nardelli, 1983) for thiomorpholine and tetrahydropyridine rings are q₂ = 0.065 (1), 0.394 (1) Å, q₃ = 0.639 (2), 0.294 (1) Å; Q_T = 0.642 (2), 0.491 (1) Å and θ = 5.7 (1), 53.3 (2)°, respectively.

The molecular structure and the crystal packing are stabilized by O—H···O intramolecular and C—H···O intermolecular interactions, respectively, with atom O3 acting as bifurcated acceptor. In intramolecular interaction, atom O2 acts as a donor to O3 generating an S(6) motif and in intermolecular interaction, atom C24 acts as a donor to atom O3 at (2 - x, -y, -z), generating a dimer of the type R₂²(18).

Related literature top

For the synthesis and biological activity of 2,6-diarylpiperidin-4-one derivatives, see: Aridoss, Balasubramanian, Parthiban, Ramachandran & Kabilan (2007); Aridoss, Balasubramanian, Parthiban & Kabilan (2007); Aridoss, Parthiban et al. (2009). For a related structure, see: Aridoss, Gayathri et al. (2009). For ring conformational analysis, see: Cremer & Pople (1975); Nardelli (1983).

Experimental top

To a solution of thiomorpholine (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.; Aridoss, Gayathri et al., 2009) in benzene was added slowly over a period of 15 minutes and 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 appropriate 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., 1994); 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-2,6-diphenyl-1-(2-thiomorpholinopropanoyl)- 1,2,5,6-tetrahydropyridine-3-carboxylate top

Crystal data top

C₂₇H₃₂N₂O₄S	Z = 2
M_r = 480.61	F(000) = 512
Triclinic, P1	D_x = 1.278 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.904 (3) Å	Cell parameters from 5338 reflections
b = 11.400 (4) Å	θ = 2.3–27.8°
c = 12.103 (4) Å	µ = 0.17 mm⁻¹
α = 93.908 (18)°	T = 293 K
β = 104.941 (15)°	Block, colorless
γ = 106.819 (16)°	0.30 × 0.25 × 0.20 mm
V = 1248.7 (7) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	5707 independent reflections
Radiation source: fine-focus sealed tube	4543 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω and ϕ scan	θ_max = 27.8°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −12→12
T_min = 0.952, T_max = 0.968	k = −14→14
26182 measured reflections	l = −15→15

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0614P)² + 0.2715P] where P = (F_o² + 2F_c²)/3
5707 reflections	(Δ/σ)_max = 0.001
309 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₂₇H₃₂N₂O₄S	γ = 106.819 (16)°
M_r = 480.61	V = 1248.7 (7) Å³
Triclinic, P1	Z = 2
a = 9.904 (3) Å	Mo Kα radiation
b = 11.400 (4) Å	µ = 0.17 mm⁻¹
c = 12.103 (4) Å	T = 293 K
α = 93.908 (18)°	0.30 × 0.25 × 0.20 mm
β = 104.941 (15)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	5707 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	4543 reflections with I > 2σ(I)
T_min = 0.952, T_max = 0.968	R_int = 0.032
26182 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.01	Δρ_max = 0.21 e Å⁻³
5707 reflections	Δρ_min = −0.36 e Å⁻³
309 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
C1	1.19148 (14)	0.27730 (12)	0.23357 (11)	0.0347 (3)
H1	1.2819	0.2883	0.2959	0.042*
C2	1.22176 (15)	0.24683 (13)	0.12043 (12)	0.0400 (3)
H2A	1.2817	0.3218	0.1013	0.048*
H2B	1.2769	0.1885	0.1293	0.048*
C3	1.08292 (15)	0.19255 (12)	0.02448 (11)	0.0371 (3)
C4	0.95026 (14)	0.14479 (11)	0.04268 (10)	0.0331 (3)
C5	0.93213 (13)	0.13505 (11)	0.16238 (10)	0.0310 (3)
H5	0.8828	0.0472	0.1626	0.037*
C6	1.10345 (14)	0.08311 (12)	0.31764 (10)	0.0337 (3)
C7	1.25989 (15)	0.11016 (13)	0.39709 (11)	0.0357 (3)
H7	1.3274	0.1358	0.3501	0.043*
C8	1.45086 (15)	0.27218 (15)	0.54032 (13)	0.0478 (4)
H8A	1.4994	0.2871	0.4801	0.057*
H8B	1.4889	0.2154	0.5853	0.057*
C9	1.4863 (2)	0.39292 (17)	0.61776 (16)	0.0611 (4)
H9A	1.4450	0.4485	0.5733	0.073*
H9B	1.5924	0.4315	0.6454	0.073*
C10	1.2279 (2)	0.29267 (17)	0.65584 (14)	0.0574 (4)
H10A	1.1697	0.2655	0.7082	0.069*
H10B	1.1886	0.3499	0.6126	0.069*
C11	1.21338 (17)	0.18191 (15)	0.57289 (12)	0.0457 (3)
H11A	1.2508	0.1239	0.6163	0.055*
H11B	1.1099	0.1405	0.5329	0.055*
C12	1.15095 (14)	0.39523 (12)	0.24545 (11)	0.0358 (3)
C13	1.12638 (16)	0.43177 (14)	0.34780 (13)	0.0448 (3)
H13	1.1291	0.3814	0.4051	0.054*
C14	1.0980 (2)	0.54136 (16)	0.36610 (16)	0.0577 (4)
H14	1.0809	0.5643	0.4352	0.069*
C15	1.0948 (2)	0.61727 (16)	0.28258 (18)	0.0640 (5)
H15	1.0773	0.6922	0.2955	0.077*
C16	1.1173 (2)	0.58217 (16)	0.18069 (17)	0.0608 (4)
H16	1.1135	0.6327	0.1235	0.073*
C17	1.14591 (18)	0.47184 (13)	0.16176 (13)	0.0471 (3)
H17	1.1618	0.4490	0.0921	0.057*
C18	0.83851 (13)	0.20571 (12)	0.19968 (11)	0.0332 (3)
C19	0.80193 (16)	0.18358 (14)	0.30119 (12)	0.0425 (3)
H19	0.8339	0.1262	0.3429	0.051*
C20	0.71920 (19)	0.24515 (16)	0.34109 (15)	0.0547 (4)
H20	0.6955	0.2294	0.4093	0.066*
C21	0.6719 (2)	0.32964 (16)	0.28039 (16)	0.0597 (4)
H21	0.6165	0.3720	0.3075	0.072*
C22	0.7062 (2)	0.35187 (16)	0.17939 (16)	0.0555 (4)
H22	0.6733	0.4090	0.1379	0.067*
C23	0.78906 (16)	0.29013 (13)	0.13889 (12)	0.0423 (3)
H23	0.8116	0.3057	0.0702	0.051*
C24	1.2782 (2)	−0.00907 (15)	0.43919 (14)	0.0524 (4)
H24A	1.3719	0.0096	0.4965	0.079*
H24B	1.2733	−0.0661	0.3751	0.079*
H24C	1.2008	−0.0457	0.4725	0.079*
C25	0.82265 (15)	0.08996 (12)	−0.05693 (11)	0.0369 (3)
C26	0.56361 (17)	−0.00482 (15)	−0.12584 (13)	0.0494 (4)
H26A	0.4891	−0.0668	−0.1038	0.059*
H26B	0.5820	−0.0430	−0.1922	0.059*
C27	0.5094 (2)	0.1005 (2)	−0.15733 (19)	0.0757 (6)
H27A	0.4967	0.1411	−0.0904	0.114*
H27B	0.4167	0.0701	−0.2167	0.114*
H27C	0.5797	0.1585	−0.1852	0.114*
N1	1.07728 (11)	0.16791 (10)	0.24818 (9)	0.0326 (2)
N2	1.29325 (11)	0.21563 (10)	0.48737 (9)	0.0336 (2)
O1	1.00568 (11)	−0.01107 (9)	0.31843 (9)	0.0454 (2)
O2	1.10662 (12)	0.19398 (11)	−0.07897 (9)	0.0520 (3)
H2	1.0283	0.1614	−0.1296	0.078*
O3	0.82742 (12)	0.08937 (11)	−0.15678 (8)	0.0539 (3)
O4	0.69839 (10)	0.03850 (9)	−0.03050 (8)	0.0406 (2)
S1	1.41530 (6)	0.37181 (4)	0.73873 (4)	0.06261 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0296 (6)	0.0326 (6)	0.0350 (6)	0.0045 (5)	0.0035 (5)	0.0060 (5)
C2	0.0337 (7)	0.0390 (7)	0.0460 (8)	0.0076 (5)	0.0137 (6)	0.0064 (6)
C3	0.0431 (7)	0.0354 (7)	0.0351 (7)	0.0139 (6)	0.0140 (6)	0.0047 (5)
C4	0.0358 (6)	0.0322 (6)	0.0299 (6)	0.0116 (5)	0.0070 (5)	0.0025 (5)
C5	0.0288 (6)	0.0298 (6)	0.0289 (6)	0.0052 (5)	0.0041 (5)	0.0032 (5)
C6	0.0370 (7)	0.0346 (7)	0.0286 (6)	0.0105 (5)	0.0090 (5)	0.0055 (5)
C7	0.0362 (7)	0.0409 (7)	0.0306 (6)	0.0146 (5)	0.0078 (5)	0.0069 (5)
C8	0.0320 (7)	0.0619 (10)	0.0434 (8)	0.0100 (7)	0.0079 (6)	0.0019 (7)
C9	0.0495 (9)	0.0547 (10)	0.0591 (10)	−0.0010 (8)	0.0049 (8)	−0.0027 (8)
C10	0.0655 (11)	0.0708 (11)	0.0464 (9)	0.0303 (9)	0.0250 (8)	0.0069 (8)
C11	0.0438 (8)	0.0530 (9)	0.0390 (7)	0.0094 (7)	0.0169 (6)	0.0063 (6)
C12	0.0307 (6)	0.0302 (6)	0.0368 (7)	0.0014 (5)	0.0032 (5)	0.0031 (5)
C13	0.0459 (8)	0.0404 (7)	0.0407 (7)	0.0057 (6)	0.0097 (6)	0.0036 (6)
C14	0.0615 (10)	0.0485 (9)	0.0599 (10)	0.0124 (8)	0.0215 (8)	−0.0046 (8)
C15	0.0691 (12)	0.0387 (9)	0.0863 (13)	0.0184 (8)	0.0259 (10)	0.0066 (8)
C16	0.0725 (11)	0.0420 (9)	0.0709 (11)	0.0196 (8)	0.0213 (9)	0.0216 (8)
C17	0.0546 (9)	0.0389 (8)	0.0446 (8)	0.0112 (7)	0.0125 (7)	0.0101 (6)
C18	0.0293 (6)	0.0327 (6)	0.0313 (6)	0.0049 (5)	0.0051 (5)	0.0003 (5)
C19	0.0429 (7)	0.0467 (8)	0.0379 (7)	0.0131 (6)	0.0130 (6)	0.0062 (6)
C20	0.0576 (10)	0.0613 (10)	0.0484 (9)	0.0173 (8)	0.0248 (8)	0.0013 (7)
C21	0.0619 (10)	0.0562 (10)	0.0693 (11)	0.0254 (8)	0.0285 (9)	−0.0019 (8)
C22	0.0611 (10)	0.0474 (9)	0.0641 (10)	0.0279 (8)	0.0167 (8)	0.0086 (8)
C23	0.0455 (8)	0.0413 (7)	0.0403 (7)	0.0150 (6)	0.0117 (6)	0.0060 (6)
C24	0.0642 (10)	0.0485 (9)	0.0429 (8)	0.0280 (8)	0.0018 (7)	0.0064 (7)
C25	0.0422 (7)	0.0358 (7)	0.0311 (6)	0.0146 (6)	0.0065 (5)	0.0017 (5)
C26	0.0395 (8)	0.0513 (9)	0.0411 (8)	0.0069 (6)	−0.0052 (6)	−0.0004 (6)
C27	0.0595 (11)	0.0746 (13)	0.0794 (13)	0.0234 (10)	−0.0081 (10)	0.0230 (11)
N1	0.0296 (5)	0.0308 (5)	0.0314 (5)	0.0059 (4)	0.0030 (4)	0.0054 (4)
N2	0.0291 (5)	0.0398 (6)	0.0302 (5)	0.0091 (4)	0.0077 (4)	0.0055 (4)
O1	0.0431 (5)	0.0415 (5)	0.0446 (5)	0.0043 (4)	0.0088 (4)	0.0161 (4)
O2	0.0516 (6)	0.0649 (7)	0.0388 (5)	0.0120 (5)	0.0204 (5)	0.0043 (5)
O3	0.0537 (6)	0.0723 (8)	0.0297 (5)	0.0162 (6)	0.0084 (4)	0.0000 (5)
O4	0.0352 (5)	0.0447 (5)	0.0327 (5)	0.0077 (4)	0.0010 (4)	0.0018 (4)
S1	0.0835 (3)	0.0571 (3)	0.0407 (2)	0.0286 (2)	0.0031 (2)	−0.00484 (18)

Geometric parameters (Å, º) top

C1—N1	1.4773 (16)	C12—C13	1.382 (2)
C1—C2	1.5142 (19)	C13—C14	1.373 (2)
C1—C12	1.5182 (19)	C13—H13	0.9300
C1—H1	0.9800	C14—C15	1.375 (3)
C2—C3	1.4861 (19)	C14—H14	0.9300
C2—H2A	0.9700	C15—C16	1.363 (3)
C2—H2B	0.9700	C15—H15	0.9300
C3—O2	1.3323 (16)	C16—C17	1.384 (2)
C3—C4	1.3501 (19)	C16—H16	0.9300
C4—C25	1.4477 (18)	C17—H17	0.9300
C4—C5	1.5126 (17)	C18—C23	1.375 (2)
C5—N1	1.4665 (16)	C18—C19	1.3867 (19)
C5—C18	1.5202 (18)	C19—C20	1.374 (2)
C5—H5	0.9800	C19—H19	0.9300
C6—O1	1.2227 (16)	C20—C21	1.367 (3)
C6—N1	1.3609 (17)	C20—H20	0.9300
C6—C7	1.5281 (18)	C21—C22	1.371 (2)
C7—N2	1.4675 (18)	C21—H21	0.9300
C7—C24	1.526 (2)	C22—C23	1.380 (2)
C7—H7	0.9800	C22—H22	0.9300
C8—N2	1.4520 (18)	C23—H23	0.9300
C8—C9	1.507 (2)	C24—H24A	0.9600
C8—H8A	0.9700	C24—H24B	0.9600
C8—H8B	0.9700	C24—H24C	0.9600
C9—S1	1.782 (2)	C25—O3	1.2212 (17)
C9—H9A	0.9700	C25—O4	1.3310 (17)
C9—H9B	0.9700	C26—O4	1.4505 (16)
C10—C11	1.507 (2)	C26—C27	1.485 (3)
C10—S1	1.792 (2)	C26—H26A	0.9700
C10—H10A	0.9700	C26—H26B	0.9700
C10—H10B	0.9700	C27—H27A	0.9600
C11—N2	1.4647 (17)	C27—H27B	0.9600
C11—H11A	0.9700	C27—H27C	0.9600
C11—H11B	0.9700	O2—H2	0.8200
C12—C17	1.382 (2)

N1—C1—C2	107.66 (11)	C12—C13—H13	119.5
N1—C1—C12	112.16 (11)	C13—C14—C15	120.20 (16)
C2—C1—C12	114.82 (11)	C13—C14—H14	119.9
N1—C1—H1	107.3	C15—C14—H14	119.9
C2—C1—H1	107.3	C16—C15—C14	119.63 (16)
C12—C1—H1	107.3	C16—C15—H15	120.2
C3—C2—C1	111.58 (11)	C14—C15—H15	120.2
C3—C2—H2A	109.3	C15—C16—C17	120.40 (16)
C1—C2—H2A	109.3	C15—C16—H16	119.8
C3—C2—H2B	109.3	C17—C16—H16	119.8
C1—C2—H2B	109.3	C12—C17—C16	120.56 (15)
H2A—C2—H2B	108.0	C12—C17—H17	119.7
O2—C3—C4	125.09 (13)	C16—C17—H17	119.7
O2—C3—C2	112.09 (12)	C23—C18—C19	118.54 (13)
C4—C3—C2	122.79 (12)	C23—C18—C5	123.75 (12)
C3—C4—C25	118.29 (12)	C19—C18—C5	117.71 (12)
C3—C4—C5	122.64 (11)	C20—C19—C18	120.98 (14)
C25—C4—C5	118.79 (11)	C20—C19—H19	119.5
N1—C5—C4	109.82 (10)	C18—C19—H19	119.5
N1—C5—C18	110.60 (10)	C21—C20—C19	119.88 (15)
C4—C5—C18	116.73 (10)	C21—C20—H20	120.1
N1—C5—H5	106.3	C19—C20—H20	120.1
C4—C5—H5	106.3	C20—C21—C22	119.83 (15)
C18—C5—H5	106.3	C20—C21—H21	120.1
O1—C6—N1	121.77 (12)	C22—C21—H21	120.1
O1—C6—C7	120.49 (12)	C21—C22—C23	120.49 (15)
N1—C6—C7	117.73 (11)	C21—C22—H22	119.8
N2—C7—C24	116.11 (11)	C23—C22—H22	119.8
N2—C7—C6	109.40 (10)	C18—C23—C22	120.26 (14)
C24—C7—C6	109.39 (12)	C18—C23—H23	119.9
N2—C7—H7	107.2	C22—C23—H23	119.9
C24—C7—H7	107.2	C7—C24—H24A	109.5
C6—C7—H7	107.2	C7—C24—H24B	109.5
N2—C8—C9	111.80 (13)	H24A—C24—H24B	109.5
N2—C8—H8A	109.3	C7—C24—H24C	109.5
C9—C8—H8A	109.3	H24A—C24—H24C	109.5
N2—C8—H8B	109.3	H24B—C24—H24C	109.5
C9—C8—H8B	109.3	O3—C25—O4	122.39 (12)
H8A—C8—H8B	107.9	O3—C25—C4	123.53 (13)
C8—C9—S1	112.18 (12)	O4—C25—C4	114.08 (11)
C8—C9—H9A	109.2	O4—C26—C27	110.13 (13)
S1—C9—H9A	109.2	O4—C26—H26A	109.6
C8—C9—H9B	109.2	C27—C26—H26A	109.6
S1—C9—H9B	109.2	O4—C26—H26B	109.6
H9A—C9—H9B	107.9	C27—C26—H26B	109.6
C11—C10—S1	112.47 (12)	H26A—C26—H26B	108.1
C11—C10—H10A	109.1	C26—C27—H27A	109.5
S1—C10—H10A	109.1	C26—C27—H27B	109.5
C11—C10—H10B	109.1	H27A—C27—H27B	109.5
S1—C10—H10B	109.1	C26—C27—H27C	109.5
H10A—C10—H10B	107.8	H27A—C27—H27C	109.5
N2—C11—C10	112.61 (13)	H27B—C27—H27C	109.5
N2—C11—H11A	109.1	C6—N1—C5	117.56 (10)
C10—C11—H11A	109.1	C6—N1—C1	125.05 (11)
N2—C11—H11B	109.1	C5—N1—C1	115.92 (10)
C10—C11—H11B	109.1	C8—N2—C11	112.46 (11)
H11A—C11—H11B	107.8	C8—N2—C7	111.81 (11)
C17—C12—C13	118.22 (14)	C11—N2—C7	111.79 (11)
C17—C12—C1	123.25 (13)	C3—O2—H2	109.5
C13—C12—C1	118.41 (12)	C25—O4—C26	116.77 (11)
C14—C13—C12	120.97 (15)	C9—S1—C10	95.98 (8)
C14—C13—H13	119.5

N1—C1—C2—C3	48.04 (14)	C18—C19—C20—C21	0.0 (2)
C12—C1—C2—C3	−77.64 (14)	C19—C20—C21—C22	0.5 (3)
C1—C2—C3—O2	164.35 (11)	C20—C21—C22—C23	−0.4 (3)
C1—C2—C3—C4	−17.41 (18)	C19—C18—C23—C22	0.6 (2)
O2—C3—C4—C25	0.3 (2)	C5—C18—C23—C22	−179.08 (13)
C2—C3—C4—C25	−177.71 (12)	C21—C22—C23—C18	−0.2 (2)
O2—C3—C4—C5	174.15 (12)	C3—C4—C25—O3	−3.3 (2)
C2—C3—C4—C5	−3.9 (2)	C5—C4—C25—O3	−177.40 (13)
C3—C4—C5—N1	−7.76 (17)	C3—C4—C25—O4	176.05 (12)
C25—C4—C5—N1	166.06 (11)	C5—C4—C25—O4	1.95 (17)
C3—C4—C5—C18	119.13 (14)	O1—C6—N1—C5	−8.07 (18)
C25—C4—C5—C18	−67.04 (15)	C7—C6—N1—C5	172.90 (10)
O1—C6—C7—N2	−110.36 (14)	O1—C6—N1—C1	−173.66 (12)
N1—C6—C7—N2	68.68 (14)	C7—C6—N1—C1	7.31 (18)
O1—C6—C7—C24	17.86 (18)	C4—C5—N1—C6	−123.91 (12)
N1—C6—C7—C24	−163.10 (12)	C18—C5—N1—C6	105.82 (13)
N2—C8—C9—S1	64.32 (17)	C4—C5—N1—C1	42.99 (14)
S1—C10—C11—N2	−61.25 (16)	C18—C5—N1—C1	−87.27 (13)
N1—C1—C12—C17	−125.18 (14)	C2—C1—N1—C6	101.21 (14)
C2—C1—C12—C17	−1.86 (18)	C12—C1—N1—C6	−131.53 (13)
N1—C1—C12—C13	58.79 (15)	C2—C1—N1—C5	−64.58 (14)
C2—C1—C12—C13	−177.89 (12)	C12—C1—N1—C5	62.67 (14)
C17—C12—C13—C14	−0.1 (2)	C9—C8—N2—C11	−63.15 (17)
C1—C12—C13—C14	176.10 (14)	C9—C8—N2—C7	170.12 (13)
C12—C13—C14—C15	−0.5 (3)	C10—C11—N2—C8	61.90 (17)
C13—C14—C15—C16	1.1 (3)	C10—C11—N2—C7	−171.36 (12)
C14—C15—C16—C17	−1.1 (3)	C24—C7—N2—C8	75.03 (16)
C13—C12—C17—C16	0.2 (2)	C6—C7—N2—C8	−160.59 (11)
C1—C12—C17—C16	−175.88 (14)	C24—C7—N2—C11	−52.06 (16)
C15—C16—C17—C12	0.5 (3)	C6—C7—N2—C11	72.31 (14)
N1—C5—C18—C23	116.73 (13)	O3—C25—O4—C26	−7.80 (19)
C4—C5—C18—C23	−9.78 (18)	C4—C25—O4—C26	172.84 (11)
N1—C5—C18—C19	−62.99 (15)	C27—C26—O4—C25	−81.20 (18)
C4—C5—C18—C19	170.50 (11)	C8—C9—S1—C10	−55.24 (14)
C23—C18—C19—C20	−0.6 (2)	C11—C10—S1—C9	53.83 (14)
C5—C18—C19—C20	179.18 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.82	1.85	2.560 (2)	144
C24—H24B···O3ⁱ	0.96	2.54	3.285 (2)	135

Symmetry code: (i) −x+2, −y, −z.

Experimental details

Crystal data
Chemical formula	C₂₇H₃₂N₂O₄S
M_r	480.61
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.904 (3), 11.400 (4), 12.103 (4)
α, β, γ (°)	93.908 (18), 104.941 (15), 106.819 (16)
V (Å³)	1248.7 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.952, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	26182, 5707, 4543
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.655

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.117, 1.01
No. of reflections	5707
No. of parameters	309
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.36

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.82	1.85	2.560 (2)	144
C24—H24B···O3ⁱ	0.96	2.54	3.285 (2)	135

Symmetry code: (i) −x+2, −y, −z.

Acknowledgements

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

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
Aridoss, G., Balasubramanian, S., Parthiban, P. & Kabilan, S. (2007). Eur. J. Med. Chem. 42, 851–860. Web of Science CrossRef PubMed CAS Google Scholar
Aridoss, G., Balasubramanian, S., Parthiban, P., Ramachandran, R. & Kabilan, S. (2007). Med. Chem. Res. 16, 188–204. Web of Science CrossRef CAS Google Scholar
Aridoss, G., Gayathri, D., Velmurugan, D., Kim, M. S. & Jeong, Y. T. (2009). Acta Cryst. E65, o1708–o1709. Web of Science CSD CrossRef IUCr Journals Google Scholar
Aridoss, G., Parthiban, P., Ramachandran, R., Prakash, M., Kabilan, S. & Jeong, Y. T. (2009). Eur. J. Med. Chem. 44, 577–592. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (1999). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Nardelli, M. (1983). Acta Cryst. C39, 1141–1142. CrossRef CAS Web of Science 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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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages o3180-o3181

doi:10.1107/S1600536809049186

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

Ethyl 4-hydr­­oxy-2,6-di­phenyl-1-(2-thio­morpholino­propano­yl)-1,2,5,6-tetra­hydro­pyridine-3-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethyl 4-hydroxy-2,6-diphenyl-1-(2-thiomorpholinopropanoyl)-1,2,5,6-tetrahydropyridine-3-carboxylate