Ethyl 1-benzoyl-4-hy­droxy-2,6-diphenyl-1,2,5,6-tetra­hydro­pyridine-3-carboxyl­ate

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

doi:10.1107/S1600536811003266

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o540

doi:10.1107/S1600536811003266

Open

access

Ethyl 1-benzoyl-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 21 January 2011; accepted 25 January 2011; online 2 February 2011)

In the title compound, C₂₇H₂₅NO₄, the tetrahydropyridine ring adopts a half-chair conformation. The three phenyl rings form dihedral angles of 66.33 (7), 87.36 (8) and 36.90 (7)° with the least-squares plane through the tetrahydropyridine ring. The molecular conformation is stabilized by an intramolecular O—H⋯O hydrogen bond, generating an S(6) motif.

Related literature

For related structures, see: Subha Nandhini et al. (2003 ); Nithya et al. (2009 ); Aravindhan et al. (2009 ); Aridoss et al. (2009 , 2010 ). For ring conformational analysis, see: Cremer & Pople (1975 ); Nardelli (1983 ).

Experimental

Crystal data

C₂₇H₂₅NO₄
M_r = 427.48
Triclinic, $[P \overline 1]$
a = 8.2784 (7) Å
b = 10.6116 (9) Å
c = 12.7572 (11) Å
α = 85.681 (4)°
β = 89.963 (4)°
γ = 82.508 (5)°
V = 1107.91 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.25 × 0.23 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.979, T_max = 0.983
20295 measured reflections
5526 independent reflections
4179 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.120
S = 1.04
5526 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.15 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	1.85	2.570 (2)	146

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/S1600536811003266/is2669sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811003266/is2669Isup2.hkl

checkCIF report

Comment top

Owing to the relevance of piperidine-containing bioactive compounds, the development of new piperidine based derivatives continues to be a subject of considerable interest. The pharmacological effects of potential new drugs depend entirely on the stereochemistry and ring conformations of the compounds and hence the crystallographic study of the title compound has been carried out.

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 = 0.344 (1) Å, q₃ = -0.288 (1) Å; Q_T = 0.4485 Å and θ = 130.02 (2)°, ϕ₂ = 205.6 (2)°, respectively. The three phenyl rings are twisted away from the best plane of the tetrahydropyridine ring by 66.33 (7), 87.36 (8) and 36.90 (7)°, respectively. The sum of the bond angles around the atom N1 [360.09 (10)°] of the tetrahydropyridine ring in the molecule is in accordance with sp² hybridization. The ethyl acetate group shows an extended conformation [C18—O3—C19—C20 = 90.67 (2)°]. 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.

Related literature top

For related structures, see: Subha Nandhini et al. (2003); Nithya et al. (2009); Aravindhan et al. (2009); Aridoss et al. (2009, 2010). For ring conformational analysis, see: Cremer & Pople (1975); Nardelli (1983).

Experimental top

To a mixture of 3-carboxyethyl-2,6-diphenylpiperidin-4-one (1 equiv.) and triethylamine (1.5 equiv.) in benzene, freshly distilled benzoyl chloride in benzene was added dropwise and stirred well at room temperature until completion. The crude mass obtained by the base work upon purification and recrystallization in distilled ethanol gave fine white crystals suitable for X-ray study.

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 title compound, showing displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Crystal packing of the title compound, viewed down the a axis. For clarity, hydrogen atoms not involved in hydrogen bonding have been omitted.

Ethyl 1-benzoyl-4-hydroxy-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-carboxylate top

Crystal data top

C₂₇H₂₅NO₄	Z = 2
M_r = 427.48	F(000) = 452
Triclinic, P1	D_x = 1.281 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2784 (7) Å	Cell parameters from 1225 reflections
b = 10.6116 (9) Å	θ = 1.6–28.4°
c = 12.7572 (11) Å	µ = 0.09 mm⁻¹
α = 85.681 (4)°	T = 293 K
β = 89.963 (4)°	Block, white
γ = 82.508 (5)°	0.25 × 0.23 × 0.20 mm
V = 1107.91 (16) Å³

Data collection top

Bruker SMART APEXII area-detector diffractometer	5526 independent reflections
Radiation source: fine-focus sealed tube	4179 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω and ϕ scans	θ_max = 28.4°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→11
T_min = 0.979, T_max = 0.983	k = −14→14
20295 measured reflections	l = −17→17

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0497P)² + 0.2116P] where P = (F_o² + 2F_c²)/3
5526 reflections	(Δ/σ)_max < 0.001
290 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₂₇H₂₅NO₄	γ = 82.508 (5)°
M_r = 427.48	V = 1107.91 (16) Å³
Triclinic, P1	Z = 2
a = 8.2784 (7) Å	Mo Kα radiation
b = 10.6116 (9) Å	µ = 0.09 mm⁻¹
c = 12.7572 (11) Å	T = 293 K
α = 85.681 (4)°	0.25 × 0.23 × 0.20 mm
β = 89.963 (4)°

Data collection top

Bruker SMART APEXII area-detector diffractometer	5526 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	4179 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.983	R_int = 0.024
20295 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 1.04	Δρ_max = 0.20 e Å⁻³
5526 reflections	Δρ_min = −0.15 e Å⁻³
290 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	0.35152 (15)	0.26735 (12)	0.41384 (9)	0.0431 (3)
H1	0.3276	0.2416	0.4870	0.052*
C2	0.44264 (18)	0.38303 (14)	0.41541 (11)	0.0551 (3)
H2A	0.4025	0.4326	0.4731	0.066*
H2B	0.5573	0.3539	0.4285	0.066*
C3	0.42551 (17)	0.46663 (12)	0.31645 (11)	0.0483 (3)
C4	0.31584 (15)	0.45704 (11)	0.23982 (9)	0.0421 (3)
C5	0.19897 (14)	0.35828 (11)	0.24886 (9)	0.0382 (2)
H5	0.0906	0.4048	0.2328	0.046*
C6	0.22569 (15)	0.25498 (11)	0.17071 (9)	0.0410 (3)
C7	0.34280 (18)	0.25430 (15)	0.09352 (12)	0.0585 (4)
H7	0.4142	0.3152	0.0911	0.070*
C8	0.3555 (2)	0.16428 (18)	0.01975 (15)	0.0758 (5)
H8	0.4340	0.1660	−0.0324	0.091*
C9	0.2530 (2)	0.07296 (16)	0.02343 (14)	0.0739 (5)
H9	0.2626	0.0117	−0.0255	0.089*
C10	0.1359 (2)	0.07199 (15)	0.09956 (12)	0.0663 (4)
H10	0.0657	0.0102	0.1020	0.080*
C11	0.12177 (19)	0.16256 (13)	0.17261 (11)	0.0528 (3)
H11	0.0416	0.1614	0.2236	0.063*
C12	0.44595 (15)	0.15211 (13)	0.36780 (10)	0.0447 (3)
C13	0.59156 (19)	0.15546 (17)	0.31517 (14)	0.0692 (4)
H13	0.6367	0.2313	0.3062	0.083*
C14	0.6700 (2)	0.0462 (2)	0.27598 (19)	0.0929 (7)
H14	0.7676	0.0494	0.2403	0.112*
C15	0.6072 (2)	−0.0660 (2)	0.28857 (17)	0.0873 (6)
H15	0.6602	−0.1385	0.2606	0.105*
C16	0.4653 (2)	−0.07137 (17)	0.34282 (16)	0.0748 (5)
H16	0.4226	−0.1482	0.3531	0.090*
C17	0.38547 (18)	0.03709 (14)	0.38216 (12)	0.0573 (4)
H17	0.2892	0.0326	0.4190	0.069*
C18	0.29783 (17)	0.55330 (12)	0.15177 (10)	0.0477 (3)
C19	0.1465 (2)	0.63209 (17)	−0.00422 (12)	0.0685 (4)
H19A	0.1880	0.7112	0.0078	0.082*
H19B	0.0311	0.6514	−0.0203	0.082*
C20	0.2327 (2)	0.5731 (2)	−0.09393 (13)	0.0832 (6)
H20A	0.3479	0.5599	−0.0799	0.125*
H20B	0.2108	0.6286	−0.1567	0.125*
H20C	0.1954	0.4927	−0.1033	0.125*
C21	0.04496 (15)	0.30444 (11)	0.40464 (10)	0.0416 (3)
C22	0.03654 (15)	0.27946 (12)	0.52150 (10)	0.0433 (3)
C23	−0.04315 (18)	0.18014 (14)	0.56215 (11)	0.0549 (3)
H23	−0.0836	0.1265	0.5172	0.066*
C24	−0.0628 (2)	0.16050 (17)	0.66984 (12)	0.0655 (4)
H24	−0.1142	0.0925	0.6971	0.079*
C25	−0.0065 (2)	0.24121 (17)	0.73612 (12)	0.0643 (4)
H25	−0.0203	0.2280	0.8083	0.077*
C26	0.0700 (2)	0.34139 (15)	0.69651 (12)	0.0620 (4)
H26	0.1068	0.3965	0.7417	0.074*
C27	0.09253 (18)	0.36049 (13)	0.58943 (11)	0.0531 (3)
H27	0.1454	0.4280	0.5628	0.064*
N1	0.19330 (12)	0.30648 (9)	0.35920 (7)	0.0388 (2)
O1	0.52511 (14)	0.55669 (10)	0.31367 (9)	0.0663 (3)
H1A	0.5089	0.6028	0.2592	0.099*
O2	0.38767 (14)	0.63583 (10)	0.13602 (9)	0.0687 (3)
O3	0.17091 (12)	0.54509 (9)	0.08975 (7)	0.0530 (2)
O4	−0.08244 (11)	0.32515 (10)	0.35338 (8)	0.0563 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0447 (6)	0.0496 (7)	0.0359 (6)	−0.0114 (5)	−0.0075 (5)	−0.0002 (5)
C2	0.0608 (8)	0.0598 (8)	0.0487 (7)	−0.0218 (7)	−0.0139 (6)	−0.0056 (6)
C3	0.0527 (7)	0.0446 (7)	0.0511 (7)	−0.0167 (6)	−0.0007 (6)	−0.0096 (5)
C4	0.0474 (7)	0.0384 (6)	0.0417 (6)	−0.0098 (5)	0.0013 (5)	−0.0042 (5)
C5	0.0418 (6)	0.0381 (6)	0.0350 (6)	−0.0079 (5)	−0.0044 (5)	−0.0006 (4)
C6	0.0457 (6)	0.0398 (6)	0.0372 (6)	−0.0047 (5)	−0.0091 (5)	−0.0016 (5)
C7	0.0539 (8)	0.0606 (9)	0.0643 (9)	−0.0121 (7)	0.0074 (7)	−0.0191 (7)
C8	0.0766 (11)	0.0824 (12)	0.0721 (11)	−0.0086 (9)	0.0160 (9)	−0.0333 (9)
C9	0.0989 (13)	0.0620 (10)	0.0636 (10)	−0.0070 (9)	−0.0032 (9)	−0.0282 (8)
C10	0.0967 (12)	0.0514 (8)	0.0556 (9)	−0.0254 (8)	−0.0139 (8)	−0.0085 (7)
C11	0.0701 (9)	0.0494 (7)	0.0417 (7)	−0.0193 (6)	−0.0052 (6)	−0.0026 (5)
C12	0.0398 (6)	0.0529 (7)	0.0400 (6)	−0.0036 (5)	−0.0081 (5)	0.0025 (5)
C13	0.0483 (8)	0.0712 (10)	0.0847 (12)	−0.0031 (7)	0.0098 (8)	0.0087 (9)
C14	0.0584 (10)	0.0983 (16)	0.1135 (17)	0.0163 (10)	0.0255 (10)	0.0017 (13)
C15	0.0693 (12)	0.0831 (13)	0.1018 (15)	0.0267 (10)	−0.0038 (10)	−0.0202 (11)
C16	0.0639 (10)	0.0571 (9)	0.1021 (14)	0.0026 (8)	−0.0138 (9)	−0.0147 (9)
C17	0.0485 (8)	0.0558 (8)	0.0685 (9)	−0.0080 (6)	0.0002 (7)	−0.0080 (7)
C18	0.0531 (7)	0.0427 (7)	0.0476 (7)	−0.0077 (6)	0.0080 (6)	−0.0022 (5)
C19	0.0756 (10)	0.0728 (10)	0.0521 (8)	−0.0055 (8)	−0.0031 (7)	0.0214 (7)
C20	0.0807 (12)	0.1220 (16)	0.0467 (9)	−0.0197 (11)	0.0016 (8)	0.0062 (9)
C21	0.0462 (7)	0.0372 (6)	0.0424 (6)	−0.0089 (5)	−0.0010 (5)	−0.0027 (5)
C22	0.0443 (6)	0.0419 (6)	0.0430 (6)	−0.0025 (5)	0.0029 (5)	−0.0030 (5)
C23	0.0579 (8)	0.0568 (8)	0.0518 (8)	−0.0168 (6)	0.0020 (6)	−0.0002 (6)
C24	0.0652 (9)	0.0736 (10)	0.0566 (9)	−0.0149 (8)	0.0087 (7)	0.0130 (8)
C25	0.0656 (9)	0.0780 (11)	0.0440 (8)	0.0082 (8)	0.0107 (7)	−0.0014 (7)
C26	0.0753 (10)	0.0596 (9)	0.0489 (8)	0.0073 (7)	−0.0004 (7)	−0.0188 (7)
C27	0.0654 (9)	0.0428 (7)	0.0514 (8)	−0.0055 (6)	0.0025 (6)	−0.0085 (6)
N1	0.0415 (5)	0.0405 (5)	0.0347 (5)	−0.0073 (4)	−0.0034 (4)	−0.0013 (4)
O1	0.0744 (7)	0.0620 (6)	0.0700 (7)	−0.0369 (5)	−0.0074 (5)	−0.0056 (5)
O2	0.0769 (7)	0.0583 (6)	0.0731 (7)	−0.0273 (5)	0.0042 (6)	0.0116 (5)
O3	0.0599 (6)	0.0546 (5)	0.0427 (5)	−0.0073 (4)	−0.0006 (4)	0.0081 (4)
O4	0.0445 (5)	0.0718 (7)	0.0530 (6)	−0.0128 (5)	−0.0049 (4)	0.0030 (5)

Geometric parameters (Å, º) top

C1—N1	1.4798 (15)	C14—H14	0.9300
C1—C12	1.5197 (19)	C15—C16	1.369 (3)
C1—C2	1.5237 (18)	C15—H15	0.9300
C1—H1	0.9800	C16—C17	1.379 (2)
C2—C3	1.4831 (19)	C16—H16	0.9300
C2—H2A	0.9700	C17—H17	0.9300
C2—H2B	0.9700	C18—O2	1.2263 (16)
C3—O1	1.3397 (15)	C18—O3	1.3315 (17)
C3—C4	1.3531 (18)	C19—O3	1.4545 (16)
C4—C18	1.4543 (18)	C19—C20	1.484 (2)
C4—C5	1.5145 (16)	C19—H19A	0.9700
C5—N1	1.4751 (14)	C19—H19B	0.9700
C5—C6	1.5315 (16)	C20—H20A	0.9600
C5—H5	0.9800	C20—H20B	0.9600
C6—C7	1.3812 (19)	C20—H20C	0.9600
C6—C11	1.3852 (18)	C21—O4	1.2276 (15)
C7—C8	1.385 (2)	C21—N1	1.3597 (16)
C7—H7	0.9300	C21—C22	1.4976 (17)
C8—C9	1.367 (3)	C22—C23	1.3833 (19)
C8—H8	0.9300	C22—C27	1.3863 (18)
C9—C10	1.372 (3)	C23—C24	1.387 (2)
C9—H9	0.9300	C23—H23	0.9300
C10—C11	1.383 (2)	C24—C25	1.371 (2)
C10—H10	0.9300	C24—H24	0.9300
C11—H11	0.9300	C25—C26	1.372 (2)
C12—C17	1.3782 (19)	C25—H25	0.9300
C12—C13	1.383 (2)	C26—C27	1.382 (2)
C13—C14	1.381 (3)	C26—H26	0.9300
C13—H13	0.9300	C27—H27	0.9300
C14—C15	1.359 (3)	O1—H1A	0.8200

N1—C1—C12	111.53 (9)	C14—C15—C16	119.40 (17)
N1—C1—C2	108.76 (10)	C14—C15—H15	120.3
C12—C1—C2	114.90 (11)	C16—C15—H15	120.3
N1—C1—H1	107.1	C15—C16—C17	120.01 (18)
C12—C1—H1	107.1	C15—C16—H16	120.0
C2—C1—H1	107.1	C17—C16—H16	120.0
C3—C2—C1	113.62 (10)	C12—C17—C16	121.14 (15)
C3—C2—H2A	108.8	C12—C17—H17	119.4
C1—C2—H2A	108.8	C16—C17—H17	119.4
C3—C2—H2B	108.8	O2—C18—O3	122.55 (12)
C1—C2—H2B	108.8	O2—C18—C4	124.16 (13)
H2A—C2—H2B	107.7	O3—C18—C4	113.28 (11)
O1—C3—C4	123.70 (12)	O3—C19—C20	109.75 (14)
O1—C3—C2	112.47 (11)	O3—C19—H19A	109.7
C4—C3—C2	123.74 (11)	C20—C19—H19A	109.7
C3—C4—C18	118.69 (11)	O3—C19—H19B	109.7
C3—C4—C5	122.01 (11)	C20—C19—H19B	109.7
C18—C4—C5	118.95 (11)	H19A—C19—H19B	108.2
N1—C5—C4	109.42 (9)	C19—C20—H20A	109.5
N1—C5—C6	113.34 (9)	C19—C20—H20B	109.5
C4—C5—C6	115.47 (10)	H20A—C20—H20B	109.5
N1—C5—H5	105.9	C19—C20—H20C	109.5
C4—C5—H5	105.9	H20A—C20—H20C	109.5
C6—C5—H5	105.9	H20B—C20—H20C	109.5
C7—C6—C11	118.09 (12)	O4—C21—N1	122.22 (11)
C7—C6—C5	122.82 (11)	O4—C21—C22	118.89 (11)
C11—C6—C5	118.96 (11)	N1—C21—C22	118.87 (11)
C6—C7—C8	121.02 (14)	C23—C22—C27	119.20 (13)
C6—C7—H7	119.5	C23—C22—C21	118.91 (12)
C8—C7—H7	119.5	C27—C22—C21	121.59 (12)
C9—C8—C7	120.12 (16)	C22—C23—C24	120.09 (14)
C9—C8—H8	119.9	C22—C23—H23	120.0
C7—C8—H8	119.9	C24—C23—H23	120.0
C8—C9—C10	119.73 (14)	C25—C24—C23	120.07 (15)
C8—C9—H9	120.1	C25—C24—H24	120.0
C10—C9—H9	120.1	C23—C24—H24	120.0
C9—C10—C11	120.26 (15)	C24—C25—C26	120.31 (14)
C9—C10—H10	119.9	C24—C25—H25	119.8
C11—C10—H10	119.9	C26—C25—H25	119.8
C10—C11—C6	120.77 (14)	C25—C26—C27	120.03 (14)
C10—C11—H11	119.6	C25—C26—H26	120.0
C6—C11—H11	119.6	C27—C26—H26	120.0
C17—C12—C13	118.23 (14)	C26—C27—C22	120.27 (14)
C17—C12—C1	118.10 (12)	C26—C27—H27	119.9
C13—C12—C1	123.64 (13)	C22—C27—H27	119.9
C14—C13—C12	120.02 (17)	C21—N1—C5	118.15 (10)
C14—C13—H13	120.0	C21—N1—C1	124.93 (10)
C12—C13—H13	120.0	C5—N1—C1	116.82 (9)
C15—C14—C13	121.17 (18)	C3—O1—H1A	109.5
C15—C14—H14	119.4	C18—O3—C19	118.01 (12)
C13—C14—H14	119.4

N1—C1—C2—C3	−39.33 (16)	C1—C12—C17—C16	−179.77 (14)
C12—C1—C2—C3	86.47 (15)	C15—C16—C17—C12	0.1 (3)
C1—C2—C3—O1	−170.79 (12)	C3—C4—C18—O2	8.2 (2)
C1—C2—C3—C4	12.3 (2)	C5—C4—C18—O2	−178.52 (12)
O1—C3—C4—C18	−3.4 (2)	C3—C4—C18—O3	−170.63 (12)
C2—C3—C4—C18	173.15 (13)	C5—C4—C18—O3	2.68 (17)
O1—C3—C4—C5	−176.51 (12)	O4—C21—C22—C23	57.04 (17)
C2—C3—C4—C5	0.1 (2)	N1—C21—C22—C23	−124.55 (13)
C3—C4—C5—N1	15.95 (16)	O4—C21—C22—C27	−116.66 (15)
C18—C4—C5—N1	−157.13 (11)	N1—C21—C22—C27	61.75 (17)
C3—C4—C5—C6	−113.35 (13)	C27—C22—C23—C24	−1.6 (2)
C18—C4—C5—C6	73.57 (14)	C21—C22—C23—C24	−175.44 (13)
N1—C5—C6—C7	−130.38 (13)	C22—C23—C24—C25	1.5 (2)
C4—C5—C6—C7	−3.03 (17)	C23—C24—C25—C26	−0.3 (2)
N1—C5—C6—C11	53.88 (14)	C24—C25—C26—C27	−0.8 (2)
C4—C5—C6—C11	−178.77 (11)	C25—C26—C27—C22	0.6 (2)
C11—C6—C7—C8	0.4 (2)	C23—C22—C27—C26	0.5 (2)
C5—C6—C7—C8	−175.42 (14)	C21—C22—C27—C26	174.22 (13)
C6—C7—C8—C9	−1.0 (3)	O4—C21—N1—C5	11.51 (17)
C7—C8—C9—C10	1.0 (3)	C22—C21—N1—C5	−166.85 (10)
C8—C9—C10—C11	−0.3 (3)	O4—C21—N1—C1	−172.21 (11)
C9—C10—C11—C6	−0.4 (2)	C22—C21—N1—C1	9.43 (17)
C7—C6—C11—C10	0.3 (2)	C4—C5—N1—C21	129.05 (11)
C5—C6—C11—C10	176.29 (13)	C6—C5—N1—C21	−100.50 (12)
N1—C1—C12—C17	−68.07 (15)	C4—C5—N1—C1	−47.53 (13)
C2—C1—C12—C17	167.57 (11)	C6—C5—N1—C1	82.92 (12)
N1—C1—C12—C13	113.98 (14)	C12—C1—N1—C21	116.28 (12)
C2—C1—C12—C13	−10.38 (18)	C2—C1—N1—C21	−115.98 (13)
C17—C12—C13—C14	1.8 (2)	C12—C1—N1—C5	−67.39 (13)
C1—C12—C13—C14	179.77 (16)	C2—C1—N1—C5	60.35 (13)
C12—C13—C14—C15	−0.4 (3)	O2—C18—O3—C19	4.6 (2)
C13—C14—C15—C16	−1.3 (3)	C4—C18—O3—C19	−176.56 (12)
C14—C15—C16—C17	1.4 (3)	C20—C19—O3—C18	90.67 (17)
C13—C12—C17—C16	−1.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2	0.82	1.85	2.570 (2)	146

Experimental details

Crystal data
Chemical formula	C₂₇H₂₅NO₄
M_r	427.48
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.2784 (7), 10.6116 (9), 12.7572 (11)
α, β, γ (°)	85.681 (4), 89.963 (4), 82.508 (5)
V (Å³)	1107.91 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.23 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.979, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	20295, 5526, 4179
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.120, 1.04
No. of reflections	5526
No. of parameters	290
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.15

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	1.85	2.570 (2)	146

Acknowledgements

This research was supported by the Industrial Technology Development Program, which was conducted by the Ministry of Knowledge Economy of the Korean Government. 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

Aravindhan, S., Ponnuswamy, S., Umamaheswari, J., Ramesh, P. & Ponnuswamy, M. N. (2009). Acta Cryst. E65, o1975. Web of Science CSD CrossRef IUCr Journals 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., Sundaramoorthy, S., Velmurugan, D., Park, K. S. & Jeong, Y. T. (2010). 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
Nithya, P., Hathwar, V. R., Kone, S., Malathi, N. & Khan, F. N. (2009). Acta Cryst. E65, o1692–o1693. Web of Science CSD CrossRef 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
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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o540

doi:10.1107/S1600536811003266

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

Ethyl 1-benzoyl-4-hy­dr­oxy-2,6-di­phenyl-1,2,5,6-tetra­hydro­pyridine-3-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethyl 1-benzoyl-4-hydroxy-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-carboxylate