Ethyl 1-[2-(1,3-benzoxazol-2-ylsulfan­yl)acet­yl]-4-hy­droxy-2,6-diphenyl-1,2,5,6-tetra­hydro­pyridine-3-carboxyl­ate

Aridoss, G.; Sundaramoorthy, S.; Velmurugan, D.; Jeong, Y.T.

doi:10.1107/S1600536811022744

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1731

doi:10.1107/S1600536811022744

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Ethyl 1-[2-(1,3-benzoxazol-2-ylsulfanyl)acetyl]-4-hydroxy-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-carboxylate

G. Aridoss,^a S. Sundaramoorthy,^b D. Velmurugan ^b and Y. T. Jeong ^a ^*

^aDepartment of Image Science and Engineering, Pukyong National University, Busan 608-739, Republic of Korea, and ^bCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: ytjeong@pknu.ac.kr

(Received 7 June 2011; accepted 13 June 2011; online 18 June 2011)

In the title compound, C₂₉H₂₆N₂O₅S, the piperidine ring adopts a half-chair conformation. The phenyl rings are oriented at dihedral angles of 75.76 (12) and 86.64 (9)° with respect to the best plane through the piperidine ring. The dihedral angle between the two phenyl rings is 30.81 (13)°. The benzoxazole ring system is approximately planar [maximum deviation = 0.016 (4) Å]. The atoms of the ethyl side chain are disordered over two sets of sites [site occupancies = 0.376 (9) and 0.624 (9)]. The molecular conformation is stabilized by an intramolecular O—H⋯O hydrogen bond, generating an S(6) motif. The crystal packing is stabilized by intermolecular C—H⋯O interactions, generating a chain running along the a axis.

Related literature

For the synthesis and biological activity of piperidin-4-one-based amides, see: Aridoss et al. (2010a ). For related structures see: Aridoss et al. (2010a,b ). For ring conformational analysis, see: Cremer & Pople (1975 ); Nardelli (1983 ).

Experimental

Crystal data

C₂₉H₂₆N₂O₅S
M_r = 514.58
Monoclinic, P 2₁ /c
a = 12.4630 (2) Å
b = 24.3243 (5) Å
c = 9.2350 (2) Å
β = 109.608 (1)°
V = 2637.28 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 293 K
0.23 × 0.2 × 0.18 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.963, T_max = 0.971
25589 measured reflections
6571 independent reflections
4020 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.128
S = 1.05
6571 reflections
343 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2	0.82	1.84	2.558 (2)	145
C13—H13⋯O2ⁱ	0.93	2.59	3.263 (2)	130
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811022744/lw2065sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811022744/lw2065Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811022744/lw2065Isup3.cml

checkCIF report

Comment top

The ORTEP diagram of the title compound is shown in Fig. 1. The tetrahydropyridine ring adopts a half-chair conformation. The puckering parameters (Cremer & Pople, 1975) and the smallest displacement asymmetry parameters (Nardelli, 1983) for this ring are q2 = 0.3543 (18) Å, q3 = 0.2996 (18) Å, Q_T = 0.4639 (17)Å and θ = 49.8 (2)°, respectively. The phenyl rings are oriented at dihedral angles of 75.76 (12) and 86.64 (9)° with respect to the best plane through the piperidine ring. The dihedral angle between the two phenyl rings is 30.81 (13)°. The sum of the bond angles around the atom N1 [359.49 (4)°] of the tetrahydropyridine ring in the molecule is in accordance with sp² hybridization.

The molecular structure is stabilized by a strong O—H···O hydrogen bond, wherein, atom O1 acts as a donor to O2, generating an S(6) motif. The crystal packing is stabilized by C—H···O intermolecular interaction which links the molecules into chain running along the a axis.

Related literature top

For the synthesis and biological activity of piperidin-4-one-based amides, see: Aridoss et al. (2010a). For related structures see: Aridoss et al. (2010a,b). For ring conformational analysis, see: Cremer & Pople (1975); Nardelli (1983).

Experimental top

The title compound was prepared from N-bromoacetyl-3-carboxyethyl -2,6-diphenyl-4-hydroxy-Δ³-tetrahydropyridine and benzoxazol -2-thiol according to the literature method (Aridoss et al., 2010a). Single crystals of the target molecule were obtained by the slow evaporation of its ethanolic solution at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Perspective view of the molecule showing the thermal ellipsoids are drawn at 30% probability level.
	Fig. 2. The crystal packing of the molecules viewed along c axis. For clarity, hydrogen atoms which are not involved in hydrogen bonding are omitted

Ethyl 1-[2-(1,3-benzoxazol-2-ylsulfanyl)acetyl]-4-hydroxy-2,6-diphenyl- 1,2,5,6-tetrahydropyridine-3-carboxylate top

Crystal data top

C₂₉H₂₆N₂O₅S	F(000) = 1080
M_r = 514.58	D_x = 1.296 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1535 reflections
a = 12.4630 (2) Å	θ = 1.7–28.3°
b = 24.3243 (5) Å	µ = 0.16 mm⁻¹
c = 9.2350 (2) Å	T = 293 K
β = 109.608 (1)°	Block, colourless
V = 2637.28 (9) Å³	0.23 × 0.2 × 0.18 mm
Z = 4

Data collection top

Bruker SMART APEXII area-detector diffractometer	6571 independent reflections
Radiation source: fine-focus sealed tube	4020 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω and ϕ scans	θ_max = 28.3°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −16→14
T_min = 0.963, T_max = 0.971	k = −32→30
25589 measured reflections	l = −11→12

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0552P)² + 0.311P] where P = (F_o² + 2F_c²)/3
6571 reflections	(Δ/σ)_max = 0.001
343 parameters	Δρ_max = 0.23 e Å⁻³
1 restraint	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₉H₂₆N₂O₅S	V = 2637.28 (9) Å³
M_r = 514.58	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.4630 (2) Å	µ = 0.16 mm⁻¹
b = 24.3243 (5) Å	T = 293 K
c = 9.2350 (2) Å	0.23 × 0.2 × 0.18 mm
β = 109.608 (1)°

Data collection top

Bruker SMART APEXII area-detector diffractometer	6571 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	4020 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.971	R_int = 0.033
25589 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	1 restraint
wR(F²) = 0.128	H-atom parameters constrained
S = 1.05	Δρ_max = 0.23 e Å⁻³
6571 reflections	Δρ_min = −0.24 e Å⁻³
343 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	Occ. (<1)
C1	0.88932 (13)	0.51361 (7)	0.12658 (18)	0.0442 (4)
H1	0.9663	0.5002	0.1408	0.053*
C2	0.81770 (15)	0.46363 (7)	0.1329 (2)	0.0512 (4)
H2A	0.7993	0.4435	0.0369	0.061*
H2B	0.8616	0.4395	0.2150	0.061*
C3	0.71060 (14)	0.47926 (7)	0.15925 (19)	0.0490 (4)
C4	0.69728 (13)	0.52718 (7)	0.22370 (19)	0.0450 (4)
C5	0.78980 (13)	0.57022 (6)	0.27182 (19)	0.0422 (4)
H5	0.8040	0.5773	0.3811	0.051*
C6	0.75751 (15)	0.62540 (7)	0.1898 (2)	0.0519 (4)
C7	0.67108 (18)	0.63139 (9)	0.0521 (2)	0.0665 (5)
H7	0.6299	0.6007	0.0042	0.080*
C8	0.6440 (3)	0.68249 (12)	−0.0170 (3)	0.1006 (9)
H8	0.5857	0.6860	−0.1109	0.121*
C9	0.7038 (3)	0.72767 (13)	0.0541 (5)	0.1234 (12)
H9	0.6859	0.7621	0.0085	0.148*
C10	0.7896 (3)	0.72256 (11)	0.1916 (5)	0.1218 (11)
H10	0.8301	0.7535	0.2393	0.146*
C11	0.8165 (2)	0.67160 (9)	0.2602 (3)	0.0862 (7)
H11	0.8746	0.6684	0.3544	0.103*
C12	0.85080 (14)	0.54573 (7)	−0.02325 (19)	0.0457 (4)
C13	0.75318 (15)	0.53281 (8)	−0.1447 (2)	0.0553 (5)
H13	0.7080	0.5035	−0.1352	0.066*
C14	0.72199 (19)	0.56263 (9)	−0.2793 (2)	0.0685 (6)
H14	0.6555	0.5538	−0.3589	0.082*
C15	0.7888 (2)	0.60518 (9)	−0.2957 (2)	0.0739 (6)
H15	0.7682	0.6251	−0.3870	0.089*
C16	0.88687 (19)	0.61857 (9)	−0.1767 (3)	0.0710 (6)
H16	0.9327	0.6473	−0.1880	0.085*
C17	0.91674 (16)	0.58939 (8)	−0.0412 (2)	0.0567 (5)
H17	0.9820	0.5991	0.0393	0.068*
C18	0.59236 (14)	0.53668 (9)	0.2550 (2)	0.0567 (5)
C19	0.4825 (7)	0.6007 (8)	0.335 (2)	0.139 (5)	0.376 (9)
H19A	0.4214	0.5893	0.2437	0.167*	0.376 (9)
H19B	0.4691	0.5857	0.4250	0.167*	0.376 (9)
C19'	0.4874 (4)	0.6022 (5)	0.3484 (7)	0.0873 (18)	0.624 (9)
H19C	0.4396	0.5707	0.3491	0.105*	0.624 (9)
H19D	0.5043	0.6211	0.4460	0.105*	0.624 (9)
C20	0.4919 (7)	0.6599 (4)	0.3442 (17)	0.139 (5)	0.376 (9)
H20A	0.5441	0.6704	0.4430	0.209*	0.376 (9)
H20B	0.4184	0.6756	0.3303	0.209*	0.376 (9)
H20C	0.5194	0.6731	0.2651	0.209*	0.376 (9)
C20'	0.4273 (4)	0.6389 (2)	0.2241 (5)	0.0873 (18)	0.624 (9)
H20D	0.4759	0.6692	0.2210	0.131*	0.624 (9)
H20E	0.3601	0.6525	0.2406	0.131*	0.624 (9)
H20F	0.4062	0.6193	0.1283	0.131*	0.624 (9)
C21	0.99471 (13)	0.55658 (6)	0.38113 (19)	0.0401 (4)
C22	1.10534 (13)	0.53591 (7)	0.3643 (2)	0.0474 (4)
H22A	1.1021	0.5412	0.2588	0.057*
H22B	1.1121	0.4968	0.3855	0.057*
C23	1.20310 (15)	0.63370 (7)	0.4034 (2)	0.0514 (4)
C24	1.13948 (18)	0.70527 (8)	0.2721 (3)	0.0639 (5)
C25	1.2373 (2)	0.71956 (8)	0.3851 (3)	0.0685 (6)
C26	1.2833 (3)	0.77171 (11)	0.4042 (4)	0.1052 (9)
H26	1.3514	0.7803	0.4813	0.126*
C27	1.2207 (4)	0.80994 (11)	0.3007 (5)	0.1154 (11)
H27	1.2474	0.8459	0.3081	0.138*
C28	1.1209 (3)	0.79739 (11)	0.1875 (4)	0.1077 (10)
H28	1.0810	0.8249	0.1213	0.129*
C29	1.0783 (2)	0.74448 (10)	0.1695 (3)	0.0895 (7)
H29	1.0109	0.7356	0.0914	0.107*
N1	0.89780 (10)	0.54863 (5)	0.26052 (15)	0.0399 (3)
N2	1.11968 (13)	0.64910 (6)	0.2867 (2)	0.0625 (4)
O1	0.63128 (11)	0.43949 (5)	0.11907 (15)	0.0671 (4)
H1A	0.5752	0.4492	0.1399	0.101*
O2	0.51125 (11)	0.50477 (6)	0.21915 (18)	0.0791 (4)
O3	0.59263 (10)	0.58358 (6)	0.32943 (16)	0.0657 (4)
O4	0.99521 (9)	0.57867 (5)	0.50028 (14)	0.0515 (3)
O5	1.28120 (11)	0.67320 (6)	0.47306 (16)	0.0682 (4)
S1	1.22926 (4)	0.56980 (2)	0.48965 (6)	0.05622 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0438 (9)	0.0380 (9)	0.0522 (9)	0.0028 (7)	0.0179 (7)	−0.0050 (7)
C2	0.0582 (10)	0.0370 (9)	0.0556 (10)	0.0000 (8)	0.0153 (8)	−0.0023 (8)
C3	0.0471 (9)	0.0430 (10)	0.0487 (9)	−0.0077 (8)	0.0051 (8)	0.0074 (8)
C4	0.0364 (8)	0.0479 (10)	0.0479 (9)	−0.0003 (7)	0.0105 (7)	0.0088 (8)
C5	0.0376 (8)	0.0429 (9)	0.0481 (9)	0.0010 (7)	0.0171 (7)	−0.0014 (7)
C6	0.0500 (10)	0.0413 (10)	0.0728 (12)	0.0085 (8)	0.0316 (9)	0.0024 (9)
C7	0.0801 (14)	0.0556 (13)	0.0687 (13)	0.0182 (10)	0.0313 (11)	0.0113 (10)
C8	0.128 (2)	0.0773 (19)	0.1017 (19)	0.0435 (18)	0.0454 (17)	0.0357 (16)
C9	0.147 (3)	0.0582 (19)	0.180 (4)	0.0325 (19)	0.075 (3)	0.044 (2)
C10	0.116 (2)	0.0432 (15)	0.205 (4)	−0.0003 (15)	0.052 (2)	0.0068 (19)
C11	0.0755 (15)	0.0451 (13)	0.133 (2)	0.0010 (11)	0.0281 (14)	−0.0042 (13)
C12	0.0493 (9)	0.0432 (10)	0.0493 (10)	0.0051 (8)	0.0228 (8)	−0.0043 (8)
C13	0.0589 (11)	0.0577 (12)	0.0508 (10)	0.0008 (9)	0.0202 (9)	−0.0053 (9)
C14	0.0766 (14)	0.0754 (15)	0.0498 (11)	0.0106 (12)	0.0163 (10)	−0.0018 (10)
C15	0.1025 (17)	0.0696 (15)	0.0538 (12)	0.0213 (13)	0.0318 (12)	0.0106 (11)
C16	0.0895 (15)	0.0556 (13)	0.0783 (15)	0.0004 (11)	0.0418 (13)	0.0099 (11)
C17	0.0603 (11)	0.0507 (11)	0.0621 (11)	−0.0005 (9)	0.0244 (9)	0.0013 (9)
C18	0.0408 (9)	0.0696 (13)	0.0564 (11)	0.0021 (9)	0.0121 (8)	0.0154 (10)
C19	0.060 (4)	0.129 (7)	0.253 (11)	−0.009 (4)	0.084 (6)	−0.055 (7)
C19'	0.067 (2)	0.126 (4)	0.074 (2)	0.0404 (19)	0.0303 (17)	0.0150 (18)
C20	0.060 (4)	0.129 (7)	0.253 (11)	−0.009 (4)	0.084 (6)	−0.055 (7)
C20'	0.067 (2)	0.126 (4)	0.074 (2)	0.0404 (19)	0.0303 (17)	0.0150 (18)
C21	0.0398 (8)	0.0328 (8)	0.0483 (9)	−0.0017 (6)	0.0156 (7)	0.0060 (7)
C22	0.0414 (9)	0.0384 (9)	0.0632 (11)	0.0018 (7)	0.0187 (8)	0.0064 (8)
C23	0.0487 (10)	0.0480 (10)	0.0617 (11)	−0.0084 (8)	0.0240 (9)	0.0026 (9)
C24	0.0726 (13)	0.0475 (12)	0.0816 (14)	−0.0018 (10)	0.0390 (11)	0.0110 (10)
C25	0.0927 (16)	0.0431 (11)	0.0836 (15)	−0.0089 (11)	0.0482 (13)	−0.0039 (11)
C26	0.142 (2)	0.0591 (17)	0.128 (2)	−0.0321 (17)	0.062 (2)	−0.0240 (16)
C27	0.174 (3)	0.0439 (16)	0.161 (3)	−0.009 (2)	0.101 (3)	−0.0040 (19)
C28	0.153 (3)	0.0565 (17)	0.150 (3)	0.0250 (18)	0.099 (2)	0.0374 (18)
C29	0.1020 (18)	0.0645 (15)	0.1127 (19)	0.0125 (13)	0.0501 (15)	0.0317 (14)
N1	0.0372 (7)	0.0358 (7)	0.0476 (8)	0.0018 (6)	0.0154 (6)	−0.0017 (6)
N2	0.0595 (9)	0.0480 (10)	0.0755 (11)	−0.0059 (8)	0.0168 (8)	0.0175 (8)
O1	0.0599 (8)	0.0576 (8)	0.0738 (9)	−0.0203 (6)	0.0092 (7)	0.0000 (7)
O2	0.0411 (7)	0.0926 (11)	0.0999 (11)	−0.0139 (7)	0.0189 (7)	0.0082 (9)
O3	0.0448 (7)	0.0847 (10)	0.0738 (9)	0.0084 (7)	0.0280 (6)	0.0025 (8)
O4	0.0459 (6)	0.0572 (8)	0.0505 (7)	−0.0026 (5)	0.0148 (5)	−0.0073 (6)
O5	0.0700 (9)	0.0599 (9)	0.0748 (9)	−0.0195 (7)	0.0246 (7)	−0.0099 (7)
S1	0.0396 (2)	0.0558 (3)	0.0685 (3)	−0.0013 (2)	0.0118 (2)	0.0148 (2)

Geometric parameters (Å, º) top

C1—N1	1.476 (2)	C18—O3	1.331 (2)
C1—C12	1.520 (2)	C19—C20	1.44 (2)
C1—C2	1.521 (2)	C19—O3	1.453 (3)
C1—H1	0.9800	C19—H19A	0.9700
C2—C3	1.484 (2)	C19—H19B	0.9700
C2—H2A	0.9700	C19'—C20'	1.449 (9)
C2—H2B	0.9700	C19'—O3	1.453 (2)
C3—O1	1.3434 (19)	C19'—H19C	0.9700
C3—C4	1.344 (2)	C19'—H19D	0.9700
C4—C18	1.449 (2)	C20—H20A	0.9600
C4—C5	1.510 (2)	C20—H20B	0.9600
C5—N1	1.4807 (19)	C20—H20C	0.9600
C5—C6	1.527 (2)	C20'—H20D	0.9600
C5—H5	0.9800	C20'—H20E	0.9600
C6—C7	1.371 (3)	C20'—H20F	0.9600
C6—C11	1.380 (3)	C21—O4	1.2226 (19)
C7—C8	1.386 (3)	C21—N1	1.354 (2)
C7—H7	0.9300	C21—C22	1.524 (2)
C8—C9	1.366 (4)	C22—S1	1.7901 (17)
C8—H8	0.9300	C22—H22A	0.9700
C9—C10	1.364 (4)	C22—H22B	0.9700
C9—H9	0.9300	C23—N2	1.277 (2)
C10—C11	1.381 (4)	C23—O5	1.365 (2)
C10—H10	0.9300	C23—S1	1.7271 (19)
C11—H11	0.9300	C24—C25	1.357 (3)
C12—C13	1.386 (2)	C24—C29	1.380 (3)
C12—C17	1.387 (2)	C24—N2	1.403 (2)
C13—C14	1.377 (3)	C25—C26	1.379 (3)
C13—H13	0.9300	C25—O5	1.390 (3)
C14—C15	1.369 (3)	C26—C27	1.374 (4)
C14—H14	0.9300	C26—H26	0.9300
C15—C16	1.381 (3)	C27—C28	1.363 (4)
C15—H15	0.9300	C27—H27	0.9300
C16—C17	1.376 (3)	C28—C29	1.381 (4)
C16—H16	0.9300	C28—H28	0.9300
C17—H17	0.9300	C29—H29	0.9300
C18—O2	1.229 (2)	O1—H1A	0.8200

N1—C1—C12	112.22 (13)	O2—C18—C4	124.2 (2)
N1—C1—C2	107.88 (13)	O3—C18—C4	113.17 (16)
C12—C1—C2	115.83 (14)	C20—C19—O3	103.2 (10)
N1—C1—H1	106.8	C20—C19—H19A	111.1
C12—C1—H1	106.8	O3—C19—H19A	111.1
C2—C1—H1	106.8	C20—C19—H19B	111.1
C3—C2—C1	111.90 (14)	O3—C19—H19B	111.1
C3—C2—H2A	109.2	H19A—C19—H19B	109.1
C1—C2—H2A	109.2	C20'—C19'—O3	110.1 (4)
C3—C2—H2B	109.2	C20'—C19'—H19C	109.6
C1—C2—H2B	109.2	O3—C19'—H19C	109.6
H2A—C2—H2B	107.9	C20'—C19'—H19D	109.6
O1—C3—C4	123.92 (16)	O3—C19'—H19D	109.6
O1—C3—C2	112.90 (15)	H19C—C19'—H19D	108.2
C4—C3—C2	123.11 (15)	C19'—C20'—H20D	109.5
C3—C4—C18	118.71 (16)	C19'—C20'—H20E	109.5
C3—C4—C5	122.42 (14)	H20D—C20'—H20E	109.5
C18—C4—C5	118.80 (16)	C19'—C20'—H20F	109.5
N1—C5—C4	110.84 (13)	H20D—C20'—H20F	109.5
N1—C5—C6	111.79 (13)	H20E—C20'—H20F	109.5
C4—C5—C6	114.55 (13)	O4—C21—N1	122.46 (14)
N1—C5—H5	106.4	O4—C21—C22	120.34 (14)
C4—C5—H5	106.4	N1—C21—C22	117.19 (14)
C6—C5—H5	106.4	C21—C22—S1	113.33 (12)
C7—C6—C11	118.61 (19)	C21—C22—H22A	108.9
C7—C6—C5	123.21 (17)	S1—C22—H22A	108.9
C11—C6—C5	118.16 (18)	C21—C22—H22B	108.9
C6—C7—C8	121.1 (2)	S1—C22—H22B	108.9
C6—C7—H7	119.5	H22A—C22—H22B	107.7
C8—C7—H7	119.5	N2—C23—O5	116.17 (16)
C9—C8—C7	119.4 (3)	N2—C23—S1	128.87 (14)
C9—C8—H8	120.3	O5—C23—S1	114.93 (13)
C7—C8—H8	120.3	C25—C24—C29	119.9 (2)
C10—C9—C8	120.3 (3)	C25—C24—N2	108.47 (18)
C10—C9—H9	119.8	C29—C24—N2	131.7 (2)
C8—C9—H9	119.8	C24—C25—C26	124.2 (2)
C9—C10—C11	120.2 (3)	C24—C25—O5	108.52 (17)
C9—C10—H10	119.9	C26—C25—O5	127.3 (2)
C11—C10—H10	119.9	C27—C26—C25	114.7 (3)
C6—C11—C10	120.4 (3)	C27—C26—H26	122.6
C6—C11—H11	119.8	C25—C26—H26	122.6
C10—C11—H11	119.8	C28—C27—C26	122.8 (3)
C13—C12—C17	118.11 (17)	C28—C27—H27	118.6
C13—C12—C1	122.93 (16)	C26—C27—H27	118.6
C17—C12—C1	118.95 (15)	C27—C28—C29	121.1 (3)
C14—C13—C12	121.07 (19)	C27—C28—H28	119.5
C14—C13—H13	119.5	C29—C28—H28	119.5
C12—C13—H13	119.5	C24—C29—C28	117.4 (3)
C15—C14—C13	120.0 (2)	C24—C29—H29	121.3
C15—C14—H14	120.0	C28—C29—H29	121.3
C13—C14—H14	120.0	C21—N1—C1	124.39 (13)
C14—C15—C16	119.9 (2)	C21—N1—C5	118.19 (13)
C14—C15—H15	120.0	C1—N1—C5	116.91 (12)
C16—C15—H15	120.0	C23—N2—C24	104.33 (17)
C17—C16—C15	119.9 (2)	C3—O1—H1A	109.5
C17—C16—H16	120.0	C18—O3—C19'	118.9 (5)
C15—C16—H16	120.0	C18—O3—C19	115.3 (7)
C16—C17—C12	120.89 (19)	C19'—O3—C19	4.8 (9)
C16—C17—H17	119.6	C23—O5—C25	102.52 (15)
C12—C17—H17	119.6	C23—S1—C22	97.35 (8)
O2—C18—O3	122.67 (17)

N1—C1—C2—C3	48.57 (18)	C29—C24—C25—C26	−1.5 (3)
C12—C1—C2—C3	−78.14 (18)	N2—C24—C25—C26	179.3 (2)
C1—C2—C3—O1	160.73 (14)	C29—C24—C25—O5	179.21 (19)
C1—C2—C3—C4	−22.4 (2)	N2—C24—C25—O5	0.0 (2)
O1—C3—C4—C18	1.2 (2)	C24—C25—C26—C27	1.5 (4)
C2—C3—C4—C18	−175.36 (15)	O5—C25—C26—C27	−179.4 (2)
O1—C3—C4—C5	178.08 (15)	C25—C26—C27—C28	−0.1 (4)
C2—C3—C4—C5	1.5 (3)	C26—C27—C28—C29	−1.1 (5)
C3—C4—C5—N1	−8.7 (2)	C25—C24—C29—C28	0.2 (3)
C18—C4—C5—N1	168.15 (13)	N2—C24—C29—C28	179.2 (2)
C3—C4—C5—C6	118.88 (17)	C27—C28—C29—C24	1.1 (4)
C18—C4—C5—C6	−64.23 (19)	O4—C21—N1—C1	−168.31 (15)
N1—C5—C6—C7	106.37 (18)	C22—C21—N1—C1	10.7 (2)
C4—C5—C6—C7	−20.8 (2)	O4—C21—N1—C5	3.2 (2)
N1—C5—C6—C11	−75.4 (2)	C22—C21—N1—C5	−177.75 (13)
C4—C5—C6—C11	157.43 (17)	C12—C1—N1—C21	−120.16 (16)
C11—C6—C7—C8	1.0 (3)	C2—C1—N1—C21	111.06 (16)
C5—C6—C7—C8	179.19 (19)	C12—C1—N1—C5	68.23 (17)
C6—C7—C8—C9	−0.6 (4)	C2—C1—N1—C5	−60.56 (17)
C7—C8—C9—C10	0.2 (5)	C4—C5—N1—C21	−132.40 (14)
C8—C9—C10—C11	−0.2 (5)	C6—C5—N1—C21	98.49 (17)
C7—C6—C11—C10	−0.9 (3)	C4—C5—N1—C1	39.75 (18)
C5—C6—C11—C10	−179.2 (2)	C6—C5—N1—C1	−89.36 (17)
C9—C10—C11—C6	0.5 (5)	O5—C23—N2—C24	−0.5 (2)
N1—C1—C12—C13	−120.99 (16)	S1—C23—N2—C24	177.45 (15)
C2—C1—C12—C13	3.5 (2)	C25—C24—N2—C23	0.3 (2)
N1—C1—C12—C17	60.14 (19)	C29—C24—N2—C23	−178.8 (2)
C2—C1—C12—C17	−175.36 (15)	O2—C18—O3—C19'	−9.8 (4)
C17—C12—C13—C14	−0.4 (3)	C4—C18—O3—C19'	171.1 (3)
C1—C12—C13—C14	−179.27 (16)	O2—C18—O3—C19	−13.3 (10)
C12—C13—C14—C15	1.2 (3)	C4—C18—O3—C19	167.7 (10)
C13—C14—C15—C16	−0.7 (3)	C20'—C19'—O3—C18	−93.0 (8)
C14—C15—C16—C17	−0.5 (3)	C20'—C19'—O3—C19	−52 (15)
C15—C16—C17—C12	1.3 (3)	C20—C19—O3—C18	−151.2 (9)
C13—C12—C17—C16	−0.9 (3)	C20—C19—O3—C19'	69 (15)
C1—C12—C17—C16	178.06 (16)	N2—C23—O5—C25	0.5 (2)
C3—C4—C18—O2	−3.9 (3)	S1—C23—O5—C25	−177.77 (13)
C5—C4—C18—O2	179.06 (17)	C24—C25—O5—C23	−0.2 (2)
C3—C4—C18—O3	175.12 (15)	C26—C25—O5—C23	−179.5 (2)
C5—C4—C18—O3	−1.9 (2)	N2—C23—S1—C22	−0.05 (19)
O4—C21—C22—S1	−23.5 (2)	O5—C23—S1—C22	177.90 (13)
N1—C21—C22—S1	157.47 (12)	C21—C22—S1—C23	−68.22 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2	0.82	1.84	2.558 (2)	145
C13—H13···O2ⁱ	0.93	2.59	3.263 (2)	130

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₉H₂₆N₂O₅S
M_r	514.58
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.4630 (2), 24.3243 (5), 9.2350 (2)
β (°)	109.608 (1)
V (Å³)	2637.28 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.23 × 0.2 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.963, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	25589, 6571, 4020
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.128, 1.05
No. of reflections	6571
No. of parameters	343
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.24

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2	0.82	1.84	2.558 (2)	145
C13—H13···O2ⁱ	0.93	2.59	3.263 (2)	130

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

This research work was supported by the second stage of the BK-21 program. SS and DV thank the TBI X-ray Facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection and the University Grants Commission (UGC&SAP) for financial support.

References

Aridoss, G., Amirthaganesan, S. & Jeong, Y. T. (2010a). Bioorg. Med. Chem. Lett. 20, 2242–2249. Web of Science CrossRef CAS PubMed Google Scholar
Aridoss, G., Sundaramoorthy, S., Velmurugan, D., Park, K. S. & Jeong, Y. T. (2010b). Acta Cryst. E66, o1982. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2008). APEX2, SAINT and SADABS. 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
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals 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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Volume 67| Part 7| July 2011| Page o1731

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

Ethyl 1-[2-(1,3-benzoxazol-2-ylsulfan­yl)acet­yl]-4-hy­dr­oxy-2,6-di­phenyl-1,2,5,6-tetra­hydro­pyridine-3-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethyl 1-[2-(1,3-benzoxazol-2-ylsulfanyl)acetyl]-4-hydroxy-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-carboxylate