Ethyl 1-[2-(1H-benzotriazol-1-yl)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/S1600536811020241

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1574

doi:10.1107/S1600536811020241

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Ethyl 1-[2-(1H-benzotriazol-1-yl)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 23 May 2011; accepted 27 May 2011; online 4 June 2011)

In the title compound, C₂₈H₂₆N₄O₄, the tetrahydropyridine ring adopts a boat conformation. The two phenyl rings form dihedral angles of 88.64 (8) and 59.28 (10)° with the best plane through the tetrahydropyridine ring. The dihedral angle between the two phenyl rings is 82.55 (10)°. The benzotriazole ring system is essentially planar, with a maximum deviation of 0.009 (1) Å from the least-squares plane. The molecular conformation is stabilized by an intramolecular O—H⋯O hydrogen bond, generating an S(6) motif.

Related literature

For the synthesis and medicinal properties of piperidin-4-one-based amides, see: Aridoss et al. (2010a ). For related structures see: Aridoss et al. (2010a, 2010b , 2011 ). For ring conformational analysis, see: Cremer & Pople (1975 ); Nardelli (1983 ).

Experimental

Crystal data

C₂₈H₂₆N₄O₄
M_r = 482.53
Monoclinic, P 2₁ /c
a = 7.9214 (2) Å
b = 21.9667 (6) Å
c = 14.5621 (4) Å
β = 95.722 (2)°
V = 2521.28 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.26 × 0.24 × 0.22 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.978, T_max = 0.981
24470 measured reflections
6280 independent reflections
4096 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.128
S = 1.04
6280 reflections
326 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.23 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	1.90	2.605 (2)	143

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/S1600536811020241/bt5557sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020241/bt5557Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811020241/bt5557Isup3.cml

checkCIF report

Comment top

In continuation of our interest on the conformation and crystal studies of piperidin-4-one based amides (Aridoss et al. 2010a, 2010b, 2011), we are reporting herewith the crystal structure of the title compound.

The molecular structure of compound (I) is illustrated in Fig.1. The sum of the bond angles around the atom N1 [358.77 (32)°] of the tetrahydropyridine ring in the molecule is in accordance with sp² hybridization. The two phenyl rings form dihedral angles of 88.64 (8) and 59.28 (10)° with the best plane through the tetrahydropyridine ring. The benzotriazole ring system is essentially planar with a maximum deviation of 0.009 (1)Å from the least squares plane. The ethyl acetate group shows an extended conformation [C26—O4—C27—C28 = 82.2 (2)°].

In the present structure tetrahydropyridine ring adopts a boat conformation with atoms C2 and C5 deviating by -0.316 (2) and -0.315 (1) Å, respectively from the least squares plane defined by the remaining atoms N1/C1/C3/C4 in the ring. The puckering parameters (Cremer & Pople, 1975) are Q = 0.5478 (16) Å; Θ = 90.33 (16) and Φ = 123.49 (16)°. The molecular structure is stabilized by a strong O—H···O hydrogen bond, wherein, atom O2 acts as a donor to O3, generating an S (6) motif.

Related literature top

For the synthesis and medicinal properties of piperidin-4-one-based amides, see: Aridoss et al. (2010a). For related structures see: Aridoss et al. (2010a, 2010b, 2011). 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 benzotriazole according to the literature method (Aridoss et al., 2010a). Slow evaporation of the ethanolic solution of the target compound at room temperature gave fine white crystals suitable for X-ray studies.

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 and PLATON (Spek, 2009).

Figures top

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

Ethyl 1-[2-(1H-benzotriazol-1-yl)acetyl]-4-hydroxy-2,6-diphenyl- 1,2,5,6-tetrahydropyridine-3-carboxylate top

Crystal data top

C₂₈H₂₆N₄O₄	F(000) = 1016
M_r = 482.53	D_x = 1.271 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1044 reflections
a = 7.9214 (2) Å	θ = 1.7–28.4°
b = 21.9667 (6) Å	µ = 0.09 mm⁻¹
c = 14.5621 (4) Å	T = 293 K
β = 95.722 (2)°	Block, colourless
V = 2521.28 (12) Å³	0.26 × 0.24 × 0.22 mm
Z = 4

Data collection top

Bruker SMART APEXII area-detector diffractometer	6280 independent reflections
Radiation source: fine-focus sealed tube	4096 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω and ϕ scans	θ_max = 28.4°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→9
T_min = 0.978, T_max = 0.981	k = −29→21
24470 measured reflections	l = −18→19

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0508P)² + 0.4558P] where P = (F_o² + 2F_c²)/3
6280 reflections	(Δ/σ)_max = 0.001
326 parameters	Δρ_max = 0.20 e Å⁻³
1 restraint	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₈H₂₆N₄O₄	V = 2521.28 (12) Å³
M_r = 482.53	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.9214 (2) Å	µ = 0.09 mm⁻¹
b = 21.9667 (6) Å	T = 293 K
c = 14.5621 (4) Å	0.26 × 0.24 × 0.22 mm
β = 95.722 (2)°

Data collection top

Bruker SMART APEXII area-detector diffractometer	6280 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	4096 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.981	R_int = 0.025
24470 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	1 restraint
wR(F²) = 0.128	H-atom parameters constrained
S = 1.04	Δρ_max = 0.20 e Å⁻³
6280 reflections	Δρ_min = −0.23 e Å⁻³
326 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
C14	−0.4394 (4)	0.29971 (18)	0.66570 (15)	0.1189 (12)
H14	−0.5497	0.3046	0.6384	0.143*
C28	0.4568 (4)	0.41609 (15)	1.23886 (19)	0.1343 (11)
H28A	0.3484	0.4043	1.2572	0.201*
H28B	0.5241	0.4337	1.2906	0.201*
H28C	0.5137	0.3809	1.2178	0.201*
C1	−0.13796 (17)	0.38583 (7)	0.83335 (10)	0.0444 (3)
H1	−0.1908	0.4243	0.8122	0.053*
C2	−0.19984 (19)	0.37148 (9)	0.92782 (10)	0.0548 (4)
H2A	−0.3192	0.3818	0.9260	0.066*
H2B	−0.1888	0.3281	0.9393	0.066*
C3	−0.10443 (19)	0.40503 (7)	1.00537 (10)	0.0494 (4)
C4	0.06433 (17)	0.41019 (7)	1.00816 (9)	0.0428 (3)
C5	0.15248 (17)	0.38475 (6)	0.92983 (9)	0.0398 (3)
H5	0.2567	0.4085	0.9274	0.048*
C6	0.20532 (17)	0.31828 (7)	0.93869 (9)	0.0423 (3)
C7	0.1435 (2)	0.27823 (8)	1.00015 (11)	0.0535 (4)
H7	0.0707	0.2924	1.0417	0.064*
C8	0.1882 (2)	0.21739 (8)	1.00086 (13)	0.0646 (5)
H8	0.1433	0.1909	1.0419	0.078*
C9	0.2973 (2)	0.19597 (9)	0.94192 (13)	0.0696 (5)
H9	0.3261	0.1549	0.9421	0.084*
C10	0.3643 (3)	0.23537 (9)	0.88223 (14)	0.0745 (5)
H10	0.4410	0.2212	0.8428	0.089*
C11	0.3185 (2)	0.29595 (8)	0.88043 (11)	0.0605 (4)
H11	0.3644	0.3222	0.8394	0.073*
C12	−0.2044 (2)	0.33717 (8)	0.76537 (10)	0.0530 (4)
C13	−0.3676 (2)	0.34412 (11)	0.72253 (11)	0.0769 (6)
H13	−0.4286	0.3793	0.7325	0.092*
C15	−0.3517 (5)	0.24853 (17)	0.64860 (16)	0.1274 (14)
H15	−0.4011	0.2189	0.6090	0.153*
C16	−0.1890 (4)	0.24064 (11)	0.69020 (15)	0.1051 (9)
H16	−0.1288	0.2055	0.6789	0.126*
C17	−0.1147 (3)	0.28529 (9)	0.74913 (12)	0.0728 (5)
H17	−0.0051	0.2800	0.7773	0.087*
C18	0.12276 (18)	0.42430 (7)	0.77372 (10)	0.0428 (3)
C19	0.01021 (19)	0.43927 (7)	0.68500 (10)	0.0492 (4)
H19A	−0.0417	0.4022	0.6594	0.059*
H19B	−0.0797	0.4667	0.6991	0.059*
C20	0.25001 (19)	0.52618 (8)	0.53605 (10)	0.0494 (4)
C21	0.13955 (17)	0.52698 (7)	0.60430 (9)	0.0418 (3)
C22	0.0838 (2)	0.58034 (8)	0.64184 (11)	0.0565 (4)
H22	0.0102	0.5804	0.6877	0.068*
C23	0.1446 (3)	0.63310 (8)	0.60675 (14)	0.0695 (5)
H23	0.1105	0.6702	0.6295	0.083*
C24	0.2553 (3)	0.63297 (10)	0.53843 (14)	0.0735 (6)
H24	0.2928	0.6700	0.5170	0.088*
C25	0.3104 (2)	0.58077 (9)	0.50207 (13)	0.0666 (5)
H25	0.3850	0.5812	0.4566	0.080*
C26	0.15896 (19)	0.43862 (7)	1.08725 (10)	0.0461 (3)
C27	0.4324 (2)	0.46121 (10)	1.16347 (14)	0.0777 (6)
H27A	0.3804	0.4976	1.1858	0.093*
H27B	0.5418	0.4724	1.1441	0.093*
N1	0.04728 (13)	0.39513 (5)	0.84073 (7)	0.0389 (3)
N2	0.10739 (15)	0.46717 (5)	0.61823 (8)	0.0451 (3)
N3	0.19402 (19)	0.43209 (6)	0.56320 (9)	0.0594 (4)
N4	0.27962 (19)	0.46712 (7)	0.51253 (10)	0.0642 (4)
O1	0.27280 (13)	0.43786 (6)	0.78083 (7)	0.0613 (3)
O2	−0.19961 (14)	0.42665 (6)	1.06894 (8)	0.0720 (4)
H2	−0.1387	0.4440	1.1097	0.108*
O3	0.09123 (14)	0.46188 (6)	1.15100 (8)	0.0624 (3)
O4	0.32511 (13)	0.43677 (5)	1.08484 (8)	0.0593 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C14	0.0988 (19)	0.204 (3)	0.0527 (12)	−0.091 (2)	0.0002 (12)	−0.0100 (17)
C28	0.116 (2)	0.176 (3)	0.0982 (19)	0.026 (2)	−0.0519 (16)	0.007 (2)
C1	0.0371 (7)	0.0475 (9)	0.0476 (8)	−0.0058 (6)	0.0002 (6)	0.0031 (6)
C2	0.0403 (8)	0.0726 (11)	0.0522 (9)	−0.0109 (8)	0.0084 (7)	−0.0044 (8)
C3	0.0456 (8)	0.0587 (10)	0.0445 (8)	−0.0008 (7)	0.0074 (6)	−0.0034 (7)
C4	0.0420 (8)	0.0444 (8)	0.0419 (7)	−0.0002 (6)	0.0028 (6)	0.0002 (6)
C5	0.0356 (7)	0.0448 (8)	0.0385 (7)	−0.0049 (6)	0.0013 (5)	0.0004 (6)
C6	0.0389 (7)	0.0469 (9)	0.0401 (7)	0.0009 (6)	−0.0007 (6)	0.0028 (6)
C7	0.0539 (9)	0.0536 (10)	0.0536 (9)	−0.0010 (8)	0.0082 (7)	0.0083 (7)
C8	0.0665 (11)	0.0542 (11)	0.0715 (11)	−0.0046 (9)	−0.0020 (9)	0.0170 (9)
C9	0.0764 (12)	0.0499 (11)	0.0795 (12)	0.0128 (9)	−0.0079 (10)	0.0050 (9)
C10	0.0820 (13)	0.0678 (13)	0.0755 (12)	0.0280 (11)	0.0164 (10)	0.0026 (10)
C11	0.0633 (10)	0.0610 (11)	0.0592 (9)	0.0139 (9)	0.0171 (8)	0.0111 (8)
C12	0.0559 (9)	0.0623 (11)	0.0405 (7)	−0.0247 (8)	0.0032 (7)	0.0053 (7)
C13	0.0573 (10)	0.1251 (18)	0.0471 (9)	−0.0358 (11)	−0.0001 (8)	0.0049 (10)
C15	0.179 (3)	0.154 (3)	0.0506 (12)	−0.122 (3)	0.0183 (16)	−0.0240 (15)
C16	0.178 (3)	0.0749 (15)	0.0656 (13)	−0.0515 (17)	0.0259 (16)	−0.0143 (11)
C17	0.1006 (15)	0.0570 (12)	0.0597 (10)	−0.0217 (11)	0.0022 (10)	−0.0040 (9)
C18	0.0433 (8)	0.0402 (8)	0.0446 (7)	−0.0058 (6)	0.0024 (6)	0.0036 (6)
C19	0.0505 (8)	0.0508 (9)	0.0455 (8)	−0.0100 (7)	0.0009 (6)	0.0094 (7)
C20	0.0462 (8)	0.0579 (10)	0.0433 (7)	−0.0033 (7)	0.0015 (6)	0.0067 (7)
C21	0.0437 (8)	0.0430 (9)	0.0372 (7)	−0.0018 (6)	−0.0032 (6)	0.0053 (6)
C22	0.0633 (10)	0.0515 (10)	0.0540 (9)	0.0050 (8)	0.0019 (8)	0.0000 (8)
C23	0.0813 (13)	0.0445 (10)	0.0782 (12)	0.0028 (9)	−0.0145 (10)	0.0011 (9)
C24	0.0757 (13)	0.0596 (12)	0.0814 (13)	−0.0179 (10)	−0.0118 (11)	0.0254 (10)
C25	0.0570 (10)	0.0812 (14)	0.0611 (10)	−0.0143 (10)	0.0030 (8)	0.0217 (10)
C26	0.0475 (8)	0.0444 (9)	0.0456 (8)	0.0028 (7)	0.0007 (6)	−0.0006 (6)
C27	0.0506 (10)	0.0928 (15)	0.0853 (13)	0.0035 (10)	−0.0154 (9)	−0.0374 (12)
N1	0.0364 (6)	0.0406 (7)	0.0394 (6)	−0.0038 (5)	0.0015 (5)	0.0034 (5)
N2	0.0535 (7)	0.0418 (7)	0.0398 (6)	−0.0020 (6)	0.0036 (5)	0.0028 (5)
N3	0.0711 (9)	0.0511 (8)	0.0566 (8)	0.0027 (7)	0.0089 (7)	−0.0066 (7)
N4	0.0684 (9)	0.0687 (10)	0.0580 (8)	0.0024 (8)	0.0187 (7)	−0.0040 (7)
O1	0.0471 (6)	0.0798 (8)	0.0560 (6)	−0.0188 (6)	0.0006 (5)	0.0189 (6)
O2	0.0507 (7)	0.1067 (10)	0.0603 (7)	0.0038 (7)	0.0141 (5)	−0.0228 (7)
O3	0.0593 (7)	0.0738 (8)	0.0534 (6)	0.0082 (6)	0.0018 (5)	−0.0188 (6)
O4	0.0438 (6)	0.0738 (8)	0.0586 (6)	−0.0018 (6)	−0.0035 (5)	−0.0157 (6)

Geometric parameters (Å, º) top

C14—C15	1.357 (4)	C12—C13	1.386 (2)
C14—C13	1.366 (3)	C13—H13	0.9300
C14—H14	0.9300	C15—C16	1.379 (4)
C28—C27	1.477 (3)	C15—H15	0.9300
C28—H28A	0.9600	C16—C17	1.394 (3)
C28—H28B	0.9600	C16—H16	0.9300
C28—H28C	0.9600	C17—H17	0.9300
C1—N1	1.4748 (17)	C18—O1	1.2196 (16)
C1—C12	1.515 (2)	C18—N1	1.3551 (17)
C1—C2	1.538 (2)	C18—C19	1.531 (2)
C1—H1	0.9800	C19—N2	1.4362 (18)
C2—C3	1.490 (2)	C19—H19A	0.9700
C2—H2A	0.9700	C19—H19B	0.9700
C2—H2B	0.9700	C20—N4	1.368 (2)
C3—O2	1.3379 (17)	C20—C21	1.388 (2)
C3—C4	1.338 (2)	C20—C25	1.400 (2)
C4—C26	1.451 (2)	C21—N2	1.3574 (18)
C4—C5	1.5031 (19)	C21—C22	1.384 (2)
C5—N1	1.4882 (16)	C22—C23	1.373 (2)
C5—C6	1.521 (2)	C22—H22	0.9300
C5—H5	0.9800	C23—C24	1.390 (3)
C6—C7	1.379 (2)	C23—H23	0.9300
C6—C11	1.384 (2)	C24—C25	1.353 (3)
C7—C8	1.382 (2)	C24—H24	0.9300
C7—H7	0.9300	C25—H25	0.9300
C8—C9	1.361 (3)	C26—O3	1.2289 (17)
C8—H8	0.9300	C26—O4	1.3207 (18)
C9—C10	1.371 (3)	C27—O4	1.4586 (19)
C9—H9	0.9300	C27—H27A	0.9700
C10—C11	1.379 (2)	C27—H27B	0.9700
C10—H10	0.9300	N2—N3	1.3478 (17)
C11—H11	0.9300	N3—N4	1.3024 (19)
C12—C17	1.376 (3)	O2—H2	0.8200

C15—C14—C13	120.9 (3)	C12—C13—H13	119.8
C15—C14—H14	119.6	C14—C15—C16	119.8 (2)
C13—C14—H14	119.6	C14—C15—H15	120.1
C27—C28—H28A	109.5	C16—C15—H15	120.1
C27—C28—H28B	109.5	C15—C16—C17	120.0 (3)
H28A—C28—H28B	109.5	C15—C16—H16	120.0
C27—C28—H28C	109.5	C17—C16—H16	120.0
H28A—C28—H28C	109.5	C12—C17—C16	119.7 (2)
H28B—C28—H28C	109.5	C12—C17—H17	120.2
N1—C1—C12	115.08 (12)	C16—C17—H17	120.2
N1—C1—C2	111.51 (11)	O1—C18—N1	123.41 (13)
C12—C1—C2	108.59 (12)	O1—C18—C19	119.99 (12)
N1—C1—H1	107.1	N1—C18—C19	116.60 (12)
C12—C1—H1	107.1	N2—C19—C18	110.90 (12)
C2—C1—H1	107.1	N2—C19—H19A	109.5
C3—C2—C1	113.18 (12)	C18—C19—H19A	109.5
C3—C2—H2A	108.9	N2—C19—H19B	109.5
C1—C2—H2A	108.9	C18—C19—H19B	109.5
C3—C2—H2B	108.9	H19A—C19—H19B	108.0
C1—C2—H2B	108.9	N4—C20—C21	109.10 (13)
H2A—C2—H2B	107.8	N4—C20—C25	130.60 (16)
O2—C3—C4	125.39 (14)	C21—C20—C25	120.29 (16)
O2—C3—C2	114.95 (13)	N2—C21—C22	133.52 (14)
C4—C3—C2	119.64 (13)	N2—C21—C20	103.65 (13)
C3—C4—C26	119.73 (13)	C22—C21—C20	122.82 (14)
C3—C4—C5	118.93 (13)	C23—C22—C21	115.50 (16)
C26—C4—C5	121.32 (12)	C23—C22—H22	122.3
N1—C5—C4	110.03 (11)	C21—C22—H22	122.3
N1—C5—C6	110.27 (11)	C22—C23—C24	122.29 (18)
C4—C5—C6	115.93 (11)	C22—C23—H23	118.9
N1—C5—H5	106.7	C24—C23—H23	118.9
C4—C5—H5	106.7	C25—C24—C23	122.18 (17)
C6—C5—H5	106.7	C25—C24—H24	118.9
C7—C6—C11	117.74 (14)	C23—C24—H24	118.9
C7—C6—C5	123.70 (13)	C24—C25—C20	116.91 (17)
C11—C6—C5	118.55 (13)	C24—C25—H25	121.5
C6—C7—C8	120.94 (16)	C20—C25—H25	121.5
C6—C7—H7	119.5	O3—C26—O4	122.96 (14)
C8—C7—H7	119.5	O3—C26—C4	123.27 (14)
C9—C8—C7	120.52 (17)	O4—C26—C4	113.76 (13)
C9—C8—H8	119.7	O4—C27—C28	111.05 (19)
C7—C8—H8	119.7	O4—C27—H27A	109.4
C8—C9—C10	119.48 (17)	C28—C27—H27A	109.4
C8—C9—H9	120.3	O4—C27—H27B	109.4
C10—C9—H9	120.3	C28—C27—H27B	109.4
C9—C10—C11	120.23 (18)	H27A—C27—H27B	108.0
C9—C10—H10	119.9	C18—N1—C1	121.35 (11)
C11—C10—H10	119.9	C18—N1—C5	116.83 (11)
C10—C11—C6	121.05 (16)	C1—N1—C5	120.59 (10)
C10—C11—H11	119.5	N3—N2—C21	110.50 (12)
C6—C11—H11	119.5	N3—N2—C19	119.84 (13)
C17—C12—C13	119.23 (17)	C21—N2—C19	129.45 (13)
C17—C12—C1	123.00 (15)	N4—N3—N2	108.89 (13)
C13—C12—C1	117.64 (17)	N3—N4—C20	107.85 (13)
C14—C13—C12	120.5 (3)	C3—O2—H2	109.5
C14—C13—H13	119.8	C26—O4—C27	118.16 (13)

N1—C1—C2—C3	35.76 (19)	N4—C20—C21—C22	−179.28 (14)
C12—C1—C2—C3	163.58 (14)	C25—C20—C21—C22	0.1 (2)
C1—C2—C3—O2	139.28 (15)	N2—C21—C22—C23	−178.43 (15)
C1—C2—C3—C4	−42.3 (2)	C20—C21—C22—C23	0.3 (2)
O2—C3—C4—C26	3.2 (2)	C21—C22—C23—C24	−0.3 (3)
C2—C3—C4—C26	−175.13 (14)	C22—C23—C24—C25	0.0 (3)
O2—C3—C4—C5	−178.42 (14)	C23—C24—C25—C20	0.3 (3)
C2—C3—C4—C5	3.3 (2)	N4—C20—C25—C24	178.81 (17)
C3—C4—C5—N1	37.76 (18)	C21—C20—C25—C24	−0.4 (2)
C26—C4—C5—N1	−143.84 (13)	C3—C4—C26—O3	−4.3 (2)
C3—C4—C5—C6	−88.21 (17)	C5—C4—C26—O3	177.29 (14)
C26—C4—C5—C6	90.18 (16)	C3—C4—C26—O4	175.16 (14)
N1—C5—C6—C7	−110.01 (15)	C5—C4—C26—O4	−3.2 (2)
C4—C5—C6—C7	15.84 (19)	O1—C18—N1—C1	173.04 (14)
N1—C5—C6—C11	68.27 (16)	C19—C18—N1—C1	−8.0 (2)
C4—C5—C6—C11	−165.88 (13)	O1—C18—N1—C5	5.6 (2)
C11—C6—C7—C8	−2.5 (2)	C19—C18—N1—C5	−175.37 (12)
C5—C6—C7—C8	175.82 (14)	C12—C1—N1—C18	74.41 (17)
C6—C7—C8—C9	1.3 (3)	C2—C1—N1—C18	−161.35 (13)
C7—C8—C9—C10	0.7 (3)	C12—C1—N1—C5	−118.65 (14)
C8—C9—C10—C11	−1.5 (3)	C2—C1—N1—C5	5.59 (18)
C9—C10—C11—C6	0.3 (3)	C4—C5—N1—C18	125.57 (13)
C7—C6—C11—C10	1.6 (2)	C6—C5—N1—C18	−105.31 (14)
C5—C6—C11—C10	−176.74 (16)	C4—C5—N1—C1	−41.94 (16)
N1—C1—C12—C17	33.9 (2)	C6—C5—N1—C1	87.18 (14)
C2—C1—C12—C17	−91.91 (17)	C22—C21—N2—N3	179.68 (16)
N1—C1—C12—C13	−150.30 (13)	C20—C21—N2—N3	0.79 (15)
C2—C1—C12—C13	83.93 (17)	C22—C21—N2—C19	−5.6 (3)
C15—C14—C13—C12	−1.3 (3)	C20—C21—N2—C19	175.49 (13)
C17—C12—C13—C14	0.8 (3)	C18—C19—N2—N3	83.85 (16)
C1—C12—C13—C14	−175.23 (16)	C18—C19—N2—C21	−90.42 (18)
C13—C14—C15—C16	1.1 (4)	C21—N2—N3—N4	−1.09 (17)
C14—C15—C16—C17	−0.4 (4)	C19—N2—N3—N4	−176.37 (13)
C13—C12—C17—C16	−0.1 (3)	N2—N3—N4—C20	0.89 (17)
C1—C12—C17—C16	175.68 (15)	C21—C20—N4—N3	−0.40 (18)
C15—C16—C17—C12	−0.1 (3)	C25—C20—N4—N3	−179.65 (16)
O1—C18—C19—N2	2.0 (2)	O3—C26—O4—C27	2.7 (2)
N1—C18—C19—N2	−177.02 (12)	C4—C26—O4—C27	−176.79 (15)
N4—C20—C21—N2	−0.24 (16)	C28—C27—O4—C26	82.2 (2)
C25—C20—C21—N2	179.10 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.82	1.90	2.605 (2)	143

Experimental details

Crystal data
Chemical formula	C₂₈H₂₆N₄O₄
M_r	482.53
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.9214 (2), 21.9667 (6), 14.5621 (4)
β (°)	95.722 (2)
V (Å³)	2521.28 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.26 × 0.24 × 0.22

Data collection
Diffractometer	Bruker SMART APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.978, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	24470, 6280, 4096
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.128, 1.04
No. of reflections	6280
No. of parameters	326
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.23

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 and 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	1.90	2.605 (2)	143

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. & Jeong, Y. T. (2011). Acta Cryst. E67, o540. Web of Science CSD CrossRef IUCr Journals 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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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl 1-[2-(1H-benzotriazol-1-yl)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-(1H-benzotriazol-1-yl)acetyl]-4-hydroxy-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-carboxylate