Ethyl 1-benzoyl-4-hy-droxy-2,6-diphenyl-1,2,5,6-tetra-hydro-pyridine-3-carboxyl-ate.

In the title compound, C(27)H(25)NO(4), the tetra-hydro-pyridine 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 tetra-hydro-pyridine ring. The mol-ecular conformation is stabilized by an intra-molecular 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 = 427.48

Triclinic,

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[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.120

S = 1.04

5526 reflections

290 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.15 e Å−3

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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811003266/is2669sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C27H25NO4	Z = 2
Mr = 427.48	F(000) = 452
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0497P)2 + 0.2116P] where P = (Fo2 + 2Fc2)/3
5526 reflections	(Δ/σ)max < 0.001
290 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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