1-(2-Chloro­acet­yl)-3-methyl-2,6-bis­(3,4,5-trimethoxy­phen­yl)piperidine-4-one

Lakshminarayana, B.N.; Shashidhara Prasad, J.; Gnanendra, C.R.; Sridhar, M.A.; Chenne Gowda, D.

doi:10.1107/S1600536809015864

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1237

doi:10.1107/S1600536809015864

Open

access

1-(2-Chloroacetyl)-3-methyl-2,6-bis(3,4,5-trimethoxyphenyl)piperidine-4-one

B. N. Lakshminarayana,^a J. Shashidhara Prasad,^a ^* C. R. Gnanendra,^b M. A. Sridhar ^a and D. Chenne Gowda ^b

^aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, and ^bDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, India
^*Correspondence e-mail: jsp@physics.uni-mysore.ac.in

(Received 18 April 2009; accepted 28 April 2009; online 7 May 2009)

In the crystal structure of the title compound, C₂₆H₃₂ClNO₈, the piperidine ring is in a twist-chair conformation, with puckering parameters Q = 0.655 (4) Å, θ = 93.1 (1) and φ = 254.4 (3)°. The ortho C atoms of the piperidine ring deviate from the plane defined by the remaining ring atoms by 0.380 (3) and −0.250 (3) Å.

Related literature

For the biological and pharmacological properties of piperidines, see: Prostakov & Gaivoronskaya (1978 ). For the biological activity of piperidones with aryl substituents at the 2 and 6 positions, see: Mobio et al. (1989 ); Ganellin & Spickett (1965 ). For ring-puckering analysis, see: Cremer & Pople (1975 ). For the synthesis, see: Baliah et al. (1983 ).

Experimental

Crystal data

C₂₆H₃₂ClNO₈
M_r = 521.98
Orthorhombic, P b c a
a = 13.8720 (8) Å
b = 16.5110 (11) Å
c = 22.8120 (16) Å
V = 5224.9 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 293 K
0.30 × 0.27 × 0.25 mm

Data collection

MacScience DIPLabo 32001 diffractometer
Absorption correction: none
8214 measured reflections
4464 independent reflections
3146 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.186
S = 1.05
4464 reflections
332 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Data collection: XPRESS (MacScience, 2002 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ) and ORTEPII (Johnson, 1976 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015864/nc2143sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809015864/nc2143Isup2.hkl

checkCIF report

Comment top

Piperidines are an important group of compounds in the field of medicinal chemistry owing to the fact that they can frequently be recognized in the structures of numerous naturally occurring alkaloid and synthetic compounds with interesting biological and pharmacological properties (Prostakov et al., 1978). Furthermore, the significant biological activities of piperridones were associated with aryl substituents at 2 and 6 positions (Ganellin & Spickett, 1965; Mobio et al., 1989). In view of the importance of such compounds the crystal structure of the title compound is reported.

The substituent at C2 is in an equatorial position as indicated by the dihedral angle of 85.18 (2)° between the piperidine and the phenyl ring. The methyl group at C5 reflects C8 and is oriented in an anti-periplanar conformation as indicated by the torsion angle of N1—C6—C5—C8 = -173.25°. The torsion angle of 180.0 (3)° for C6—N1—C9—O10 shows that O10 is also in an anti-periplanar conformation. The methoxy groups at C27, C25, C17 and C15 are nearly planar with the phenyl ring whereas the methoxy group at C26 and C16 is nearly orthogonal to the phenyl rings.

Related literature top

For the biological and pharmacological properties of piperidines, see: Prostakov & Gaivoronskaya (1978). For biological activity of piperidones with aryl substituents at the 2 and 6 positions, see: Mobio et al. (1989); Ganellin & Spickett (1965). For ring-puckering analysis, see: Cremer & Pople (1975). For the synthesis, see: Baliah et al. (1983).

Experimental top

To a well stirred solution of 3-methyl-2,6-bis(3,4,5-trimethoxyphenyl)piperidine-4-one (Baliah et al., 1983) (5 mmol) and triethylamine(5 mmol) in 30 ml of benzene, chloroacetyl chloride (5 mmol) in 20 ml benzene was added dropwise within about an hour. The resulting mixture was stirred for about 4 hours at room temperature. Afterwards the mixture was quenched in cold water and the organic layer was extracted with ethyl acetate, washed with 5% sodium bicarbonate solution and dried over anhydrous sodium sulphate. Slow evaporation of the solvent leads to crystals of 1-(2-chloroacetyl)-3-methyl-2,6-bis(3,4,5-trimethoxyphenyl) piperidine-4-one.

Computing details top

Data collection: XPRESS (MacScience, 2002); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and ORTEPII (Johnson, 1976); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

Fig. 1. Crystal structure of the title compound with labelling and 50% probability displacement ellipsoids.

1-(2-Chloroacetyl)-3-methyl-2,6-bis(3,4,5-trimethoxyphenyl)piperidine-4-one top

Crystal data top

C₂₆H₃₂ClNO₈	F(000) = 2208
M_r = 521.98	D_x = 1.327 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8214 reflections
a = 13.8720 (8) Å	θ = 2.9–25.0°
b = 16.5110 (11) Å	µ = 0.20 mm⁻¹
c = 22.8120 (16) Å	T = 293 K
V = 5224.9 (6) Å³	Block, white
Z = 8	0.30 × 0.27 × 0.25 mm

Data collection top

MacScience DIPLabo 32001 diffractometer	3146 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.027
Graphite monochromator	θ_max = 25.0°, θ_min = 2.9°
Detector resolution: 10.0 pixels mm^-1	h = −16→16
ω scans	k = −19→19
8214 measured reflections	l = −27→26
4464 independent reflections

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.186	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0931P)² + 2.926P] where P = (F_o² + 2F_c²)/3
4464 reflections	(Δ/σ)_max < 0.001
332 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₂₆H₃₂ClNO₈	V = 5224.9 (6) Å³
M_r = 521.98	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 13.8720 (8) Å	µ = 0.20 mm⁻¹
b = 16.5110 (11) Å	T = 293 K
c = 22.8120 (16) Å	0.30 × 0.27 × 0.25 mm

Data collection top

MacScience DIPLabo 32001 diffractometer	3146 reflections with I > 2σ(I)
8214 measured reflections	R_int = 0.027
4464 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.186	H-atom parameters constrained
S = 1.05	Δρ_max = 0.47 e Å⁻³
4464 reflections	Δρ_min = −0.39 e Å⁻³
332 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
Cl12	0.14569 (9)	−0.00580 (6)	0.36264 (6)	0.1014 (5)
O7	0.0245 (3)	−0.4484 (3)	0.28056 (17)	0.1467 (19)
O10	0.07651 (19)	−0.14395 (16)	0.42507 (10)	0.0742 (9)
O19	0.49642 (15)	−0.28235 (15)	0.40351 (9)	0.0623 (8)
O21	0.57332 (13)	−0.19912 (15)	0.31391 (9)	0.0584 (8)
O23	0.46432 (15)	−0.15115 (15)	0.22323 (9)	0.0595 (8)
O31	0.27178 (17)	−0.31372 (15)	0.56956 (9)	0.0649 (8)
O33	0.26328 (19)	−0.47563 (15)	0.57353 (9)	0.0725 (9)
O35	0.1596 (2)	−0.55902 (15)	0.49519 (11)	0.0847 (10)
N1	0.12281 (16)	−0.24570 (15)	0.36489 (10)	0.0473 (8)
C2	0.0590 (2)	−0.3025 (2)	0.39713 (13)	0.0524 (10)
C3	−0.0007 (3)	−0.3497 (2)	0.35294 (16)	0.0690 (14)
C4	0.0569 (3)	−0.3931 (2)	0.30853 (16)	0.0760 (16)
C5	0.1608 (3)	−0.3656 (2)	0.30122 (14)	0.0603 (11)
C6	0.1732 (2)	−0.27421 (18)	0.31092 (12)	0.0476 (10)
C8	0.2024 (4)	−0.3910 (3)	0.24254 (19)	0.0953 (19)
C9	0.1181 (2)	−0.1667 (2)	0.38063 (14)	0.0537 (11)
C11	0.1658 (3)	−0.10579 (19)	0.34041 (16)	0.0613 (12)
C13	0.2804 (2)	−0.25428 (18)	0.31204 (12)	0.0447 (9)
C14	0.3213 (2)	−0.21277 (19)	0.26566 (12)	0.0488 (10)
C15	0.4183 (2)	−0.19340 (19)	0.26646 (12)	0.0485 (10)
C16	0.4755 (2)	−0.21760 (19)	0.31333 (13)	0.0497 (10)
C17	0.4349 (2)	−0.26141 (19)	0.35897 (12)	0.0482 (10)
C18	0.3374 (2)	−0.27934 (18)	0.35895 (12)	0.0466 (9)
C20	0.4600 (3)	−0.3312 (2)	0.44945 (14)	0.0661 (11)
C22	0.5942 (2)	−0.1200 (2)	0.33503 (18)	0.0742 (14)
C24	0.4061 (3)	−0.1076 (2)	0.18305 (15)	0.0661 (11)
C25	0.1140 (2)	−0.3524 (2)	0.44265 (13)	0.0507 (10)
C26	0.1100 (2)	−0.4354 (2)	0.44530 (14)	0.0576 (11)
C27	0.1605 (3)	−0.4770 (2)	0.48873 (14)	0.0593 (11)
C28	0.2159 (2)	−0.4349 (2)	0.52945 (12)	0.0551 (11)
C29	0.2184 (2)	−0.3514 (2)	0.52730 (12)	0.0520 (10)
C30	0.1675 (2)	−0.3100 (2)	0.48416 (13)	0.0521 (10)
C32	0.2524 (3)	−0.2308 (2)	0.58099 (17)	0.0713 (12)
C34	0.3539 (3)	−0.5089 (3)	0.55613 (19)	0.0890 (17)
C36	0.1045 (4)	−0.6052 (2)	0.4561 (2)	0.0960 (18)
H2	0.01350	−0.26880	0.41910	0.0630*
H3A	−0.04010	−0.38860	0.37390	0.0830*
H3B	−0.04380	−0.31240	0.33310	0.0830*
H5	0.19860	−0.39300	0.33160	0.0720*
H6	0.14450	−0.24620	0.27730	0.0570*
H8A	0.18970	−0.44750	0.23610	0.1420*
H8B	0.27080	−0.38190	0.24250	0.1420*
H8C	0.17310	−0.35970	0.21190	0.1420*
H11A	0.14120	−0.11290	0.30100	0.0740*
H11B	0.23470	−0.11600	0.33950	0.0740*
H14	0.28350	−0.19780	0.23380	0.0590*
H18	0.31020	−0.30790	0.39000	0.0560*
H20A	0.40750	−0.30360	0.46830	0.0990*
H20B	0.51010	−0.34130	0.47750	0.0990*
H20C	0.43750	−0.38170	0.43370	0.0990*
H22A	0.56350	−0.08060	0.31040	0.1120*
H22B	0.66270	−0.11150	0.33460	0.1120*
H22C	0.57060	−0.11460	0.37440	0.1120*
H24A	0.37270	−0.14500	0.15800	0.0990*
H24B	0.44600	−0.07280	0.15970	0.0990*
H24C	0.36010	−0.07550	0.20420	0.0990*
H26	0.07340	−0.46390	0.41810	0.0690*
H30	0.16930	−0.25370	0.48300	0.0630*
H32A	0.27190	−0.19880	0.54790	0.1070*
H32B	0.28760	−0.21390	0.61510	0.1070*
H32C	0.18460	−0.22360	0.58770	0.1070*
H34A	0.34540	−0.54120	0.52150	0.1340*
H34B	0.37900	−0.54200	0.58710	0.1340*
H34C	0.39830	−0.46570	0.54800	0.1340*
H36A	0.03760	−0.59130	0.46030	0.1440*
H36B	0.11310	−0.66170	0.46460	0.1440*
H36C	0.12490	−0.59440	0.41670	0.1440*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl12	0.1112 (9)	0.0590 (6)	0.1341 (10)	−0.0100 (6)	0.0317 (8)	−0.0153 (6)
O7	0.159 (3)	0.153 (4)	0.128 (3)	−0.093 (3)	0.024 (3)	−0.062 (3)
O10	0.0898 (18)	0.0728 (17)	0.0599 (14)	0.0103 (14)	0.0180 (14)	0.0001 (12)
O19	0.0498 (12)	0.0887 (18)	0.0483 (12)	0.0076 (11)	−0.0098 (10)	0.0087 (11)
O21	0.0394 (11)	0.0803 (16)	0.0554 (12)	0.0056 (10)	0.0030 (10)	−0.0077 (11)
O23	0.0507 (12)	0.0819 (16)	0.0460 (11)	0.0024 (11)	0.0044 (10)	0.0106 (11)
O31	0.0698 (14)	0.0686 (15)	0.0563 (13)	0.0078 (12)	−0.0193 (12)	−0.0053 (11)
O33	0.0930 (18)	0.0727 (16)	0.0519 (12)	0.0264 (14)	−0.0143 (12)	0.0041 (11)
O35	0.123 (2)	0.0532 (15)	0.0780 (17)	0.0040 (14)	−0.0279 (16)	0.0027 (13)
N1	0.0439 (13)	0.0544 (15)	0.0437 (13)	−0.0017 (11)	−0.0038 (11)	0.0064 (11)
C2	0.0450 (16)	0.065 (2)	0.0471 (17)	−0.0039 (14)	−0.0004 (14)	0.0133 (14)
C3	0.0561 (19)	0.082 (3)	0.069 (2)	−0.0179 (18)	−0.0134 (18)	0.0181 (19)
C4	0.091 (3)	0.078 (3)	0.059 (2)	−0.032 (2)	−0.010 (2)	−0.0022 (19)
C5	0.074 (2)	0.059 (2)	0.0480 (17)	−0.0071 (16)	−0.0056 (16)	−0.0033 (15)
C6	0.0459 (16)	0.0573 (19)	0.0395 (14)	−0.0012 (13)	−0.0030 (13)	0.0037 (13)
C8	0.122 (4)	0.084 (3)	0.080 (3)	−0.014 (3)	0.013 (3)	−0.028 (2)
C9	0.0534 (18)	0.059 (2)	0.0488 (17)	0.0052 (14)	−0.0093 (15)	0.0025 (15)
C11	0.063 (2)	0.053 (2)	0.068 (2)	−0.0030 (15)	0.0041 (17)	0.0006 (16)
C13	0.0458 (15)	0.0477 (16)	0.0405 (14)	0.0050 (13)	−0.0035 (13)	−0.0027 (12)
C14	0.0482 (16)	0.0592 (19)	0.0391 (15)	0.0065 (13)	−0.0035 (13)	0.0010 (13)
C15	0.0464 (16)	0.0610 (19)	0.0382 (15)	0.0056 (14)	0.0041 (13)	−0.0047 (13)
C16	0.0434 (16)	0.0617 (19)	0.0440 (16)	0.0083 (13)	0.0020 (13)	−0.0080 (14)
C17	0.0460 (16)	0.0606 (19)	0.0381 (15)	0.0123 (14)	−0.0033 (13)	−0.0044 (13)
C18	0.0491 (16)	0.0526 (18)	0.0382 (14)	0.0045 (13)	−0.0007 (13)	0.0010 (13)
C20	0.074 (2)	0.072 (2)	0.0524 (19)	0.0114 (18)	−0.0165 (18)	0.0106 (17)
C22	0.0535 (19)	0.091 (3)	0.078 (2)	−0.0043 (19)	0.0008 (19)	−0.019 (2)
C24	0.065 (2)	0.078 (2)	0.0553 (19)	0.0018 (18)	0.0036 (17)	0.0149 (17)
C25	0.0483 (16)	0.060 (2)	0.0438 (16)	−0.0018 (14)	−0.0009 (14)	0.0072 (14)
C26	0.066 (2)	0.058 (2)	0.0489 (17)	−0.0037 (16)	−0.0071 (16)	0.0021 (15)
C27	0.075 (2)	0.0498 (19)	0.0531 (18)	0.0052 (16)	−0.0015 (17)	0.0044 (15)
C28	0.066 (2)	0.059 (2)	0.0404 (15)	0.0137 (16)	−0.0069 (15)	0.0030 (14)
C29	0.0525 (17)	0.061 (2)	0.0424 (16)	0.0044 (14)	−0.0017 (14)	−0.0024 (14)
C30	0.0540 (17)	0.0533 (18)	0.0491 (16)	0.0016 (14)	−0.0026 (15)	0.0063 (14)
C32	0.080 (2)	0.064 (2)	0.070 (2)	−0.0091 (18)	−0.011 (2)	−0.0067 (18)
C34	0.096 (3)	0.085 (3)	0.086 (3)	0.038 (2)	−0.026 (2)	−0.012 (2)
C36	0.147 (4)	0.056 (2)	0.085 (3)	−0.007 (3)	−0.022 (3)	−0.010 (2)

Geometric parameters (Å, º) top

Cl12—C11	1.749 (3)	C27—C28	1.392 (5)
O7—C4	1.201 (6)	C28—C29	1.380 (5)
O10—C9	1.225 (4)	C29—C30	1.391 (4)
O19—C17	1.371 (3)	C2—H2	0.9800
O19—C20	1.416 (4)	C3—H3A	0.9700
O21—C16	1.391 (3)	C3—H3B	0.9700
O21—C22	1.422 (4)	C5—H5	0.9800
O23—C15	1.366 (4)	C6—H6	0.9800
O23—C24	1.418 (4)	C8—H8A	0.9600
O31—C29	1.366 (4)	C8—H8B	0.9600
O31—C32	1.419 (4)	C8—H8C	0.9600
O33—C28	1.377 (4)	C11—H11A	0.9700
O33—C34	1.428 (5)	C11—H11B	0.9700
O35—C27	1.362 (4)	C14—H14	0.9300
O35—C36	1.400 (5)	C18—H18	0.9300
N1—C2	1.485 (4)	C20—H20A	0.9600
N1—C6	1.492 (4)	C20—H20B	0.9600
N1—C9	1.355 (4)	C20—H20C	0.9600
C2—C3	1.520 (5)	C22—H22A	0.9600
C2—C25	1.529 (4)	C22—H22B	0.9600
C3—C4	1.476 (5)	C22—H22C	0.9600
C4—C5	1.520 (6)	C24—H24A	0.9600
C5—C6	1.535 (4)	C24—H24B	0.9600
C5—C8	1.517 (6)	C24—H24C	0.9600
C6—C13	1.523 (4)	C26—H26	0.9300
C9—C11	1.514 (5)	C30—H30	0.9300
C13—C14	1.382 (4)	C32—H32A	0.9600
C13—C18	1.393 (4)	C32—H32B	0.9600
C14—C15	1.383 (4)	C32—H32C	0.9600
C15—C16	1.390 (4)	C34—H34A	0.9600
C16—C17	1.387 (4)	C34—H34B	0.9600
C17—C18	1.385 (4)	C34—H34C	0.9600
C25—C26	1.373 (5)	C36—H36A	0.9600
C25—C30	1.392 (4)	C36—H36B	0.9600
C26—C27	1.394 (5)	C36—H36C	0.9600

C17—O19—C20	118.0 (3)	C4—C5—H5	107.00
C16—O21—C22	113.8 (2)	C6—C5—H5	107.00
C15—O23—C24	117.4 (2)	C8—C5—H5	107.00
C29—O31—C32	117.8 (3)	N1—C6—H6	108.00
C28—O33—C34	113.9 (3)	C5—C6—H6	108.00
C27—O35—C36	118.5 (3)	C13—C6—H6	108.00
C2—N1—C6	119.3 (2)	C5—C8—H8A	109.00
C2—N1—C9	116.6 (2)	C5—C8—H8B	109.00
C6—N1—C9	123.0 (2)	C5—C8—H8C	109.00
N1—C2—C3	108.7 (2)	H8A—C8—H8B	109.00
N1—C2—C25	112.3 (2)	H8A—C8—H8C	110.00
C3—C2—C25	116.5 (3)	H8B—C8—H8C	109.00
C2—C3—C4	114.2 (3)	Cl12—C11—H11A	109.00
O7—C4—C3	122.1 (4)	Cl12—C11—H11B	109.00
O7—C4—C5	121.6 (4)	C9—C11—H11A	109.00
C3—C4—C5	116.3 (3)	C9—C11—H11B	109.00
C4—C5—C6	112.6 (3)	H11A—C11—H11B	108.00
C4—C5—C8	112.0 (3)	C13—C14—H14	120.00
C6—C5—C8	110.9 (3)	C15—C14—H14	120.00
N1—C6—C5	112.1 (2)	C13—C18—H18	120.00
N1—C6—C13	112.1 (2)	C17—C18—H18	120.00
C5—C6—C13	108.9 (3)	O19—C20—H20A	109.00
O10—C9—N1	122.5 (3)	O19—C20—H20B	110.00
O10—C9—C11	120.2 (3)	O19—C20—H20C	109.00
N1—C9—C11	117.3 (3)	H20A—C20—H20B	109.00
Cl12—C11—C9	112.4 (3)	H20A—C20—H20C	109.00
C6—C13—C14	119.7 (2)	H20B—C20—H20C	110.00
C6—C13—C18	120.2 (2)	O21—C22—H22A	110.00
C14—C13—C18	120.1 (3)	O21—C22—H22B	109.00
C13—C14—C15	120.3 (3)	O21—C22—H22C	109.00
O23—C15—C14	124.3 (3)	H22A—C22—H22B	110.00
O23—C15—C16	115.8 (2)	H22A—C22—H22C	109.00
C14—C15—C16	119.9 (3)	H22B—C22—H22C	109.00
O21—C16—C15	120.1 (3)	O23—C24—H24A	109.00
O21—C16—C17	120.2 (3)	O23—C24—H24B	110.00
C15—C16—C17	119.7 (3)	O23—C24—H24C	110.00
O19—C17—C16	115.8 (2)	H24A—C24—H24B	109.00
O19—C17—C18	123.7 (3)	H24A—C24—H24C	109.00
C16—C17—C18	120.5 (3)	H24B—C24—H24C	109.00
C13—C18—C17	119.4 (3)	C25—C26—H26	120.00
C2—C25—C26	123.2 (3)	C27—C26—H26	120.00
C2—C25—C30	117.2 (3)	C25—C30—H30	120.00
C26—C25—C30	119.6 (3)	C29—C30—H30	120.00
C25—C26—C27	120.2 (3)	O31—C32—H32A	109.00
O35—C27—C26	124.2 (3)	O31—C32—H32B	109.00
O35—C27—C28	115.4 (3)	O31—C32—H32C	110.00
C26—C27—C28	120.4 (3)	H32A—C32—H32B	110.00
O33—C28—C27	120.5 (3)	H32A—C32—H32C	109.00
O33—C28—C29	120.1 (3)	H32B—C32—H32C	109.00
C27—C28—C29	119.3 (3)	O33—C34—H34A	110.00
O31—C29—C28	116.3 (3)	O33—C34—H34B	110.00
O31—C29—C30	123.4 (3)	O33—C34—H34C	109.00
C28—C29—C30	120.2 (3)	H34A—C34—H34B	110.00
C25—C30—C29	120.3 (3)	H34A—C34—H34C	109.00
N1—C2—H2	106.00	H34B—C34—H34C	109.00
C3—C2—H2	106.00	O35—C36—H36A	109.00
C25—C2—H2	106.00	O35—C36—H36B	109.00
C2—C3—H3A	109.00	O35—C36—H36C	110.00
C2—C3—H3B	109.00	H36A—C36—H36B	109.00
C4—C3—H3A	109.00	H36A—C36—H36C	110.00
C4—C3—H3B	109.00	H36B—C36—H36C	109.00
H3A—C3—H3B	108.00

C20—O19—C17—C18	5.9 (4)	C4—C5—C6—C13	171.4 (3)
C20—O19—C17—C16	−176.3 (3)	C5—C6—C13—C18	−69.9 (3)
C22—O21—C16—C17	−97.6 (3)	N1—C6—C13—C18	54.7 (4)
C22—O21—C16—C15	83.5 (4)	N1—C6—C13—C14	−126.7 (3)
C24—O23—C15—C14	16.4 (4)	C5—C6—C13—C14	108.6 (3)
C24—O23—C15—C16	−163.9 (3)	N1—C9—C11—Cl12	175.0 (2)
C32—O31—C29—C30	19.2 (4)	O10—C9—C11—Cl12	−4.3 (4)
C32—O31—C29—C28	−160.1 (3)	C6—C13—C18—C17	179.4 (3)
C34—O33—C28—C29	−100.9 (4)	C18—C13—C14—C15	−2.3 (5)
C34—O33—C28—C27	82.9 (4)	C14—C13—C18—C17	0.8 (4)
C36—O35—C27—C28	179.3 (3)	C6—C13—C14—C15	179.2 (3)
C36—O35—C27—C26	−0.2 (5)	C13—C14—C15—C16	1.7 (5)
C9—N1—C2—C25	−103.5 (3)	C13—C14—C15—O23	−178.6 (3)
C6—N1—C9—C11	0.7 (4)	O23—C15—C16—O21	−0.6 (4)
C2—N1—C6—C5	−7.8 (3)	O23—C15—C16—C17	−179.5 (3)
C2—N1—C9—O10	11.9 (4)	C14—C15—C16—O21	179.2 (3)
C9—N1—C2—C3	126.2 (3)	C14—C15—C16—C17	0.3 (5)
C6—N1—C2—C3	−42.4 (3)	C15—C16—C17—O19	−179.6 (3)
C2—N1—C9—C11	−167.4 (3)	C15—C16—C17—C18	−1.7 (5)
C6—N1—C9—O10	−180.0 (3)	O21—C16—C17—C18	179.4 (3)
C9—N1—C6—C5	−175.6 (3)	O21—C16—C17—O19	1.5 (4)
C6—N1—C2—C25	88.0 (3)	O19—C17—C18—C13	178.9 (3)
C9—N1—C6—C13	61.6 (3)	C16—C17—C18—C13	1.2 (4)
C2—N1—C6—C13	−130.7 (3)	C2—C25—C30—C29	179.2 (3)
C3—C2—C25—C26	−1.1 (4)	C30—C25—C26—C27	−1.0 (5)
C3—C2—C25—C30	−178.8 (3)	C26—C25—C30—C29	1.4 (4)
N1—C2—C3—C4	55.7 (4)	C2—C25—C26—C27	−178.7 (3)
N1—C2—C25—C26	−127.3 (3)	C25—C26—C27—C28	−0.5 (5)
C25—C2—C3—C4	−72.3 (4)	C25—C26—C27—O35	179.0 (3)
N1—C2—C25—C30	55.0 (3)	O35—C27—C28—O33	−1.7 (5)
C2—C3—C4—C5	−17.8 (4)	O35—C27—C28—C29	−177.9 (3)
C2—C3—C4—O7	160.5 (4)	C26—C27—C28—C29	1.6 (5)
C3—C4—C5—C8	−159.8 (3)	C26—C27—C28—O33	177.9 (3)
O7—C4—C5—C6	147.7 (4)	O33—C28—C29—O31	1.8 (4)
C3—C4—C5—C6	−34.0 (4)	C27—C28—C29—C30	−1.2 (4)
O7—C4—C5—C8	21.9 (5)	O33—C28—C29—C30	−177.5 (3)
C8—C5—C6—C13	−62.2 (4)	C27—C28—C29—O31	178.1 (3)
C8—C5—C6—N1	173.2 (3)	O31—C29—C30—C25	−179.6 (3)
C4—C5—C6—N1	46.8 (3)	C28—C29—C30—C25	−0.3 (4)

Experimental details

Crystal data
Chemical formula	C₂₆H₃₂ClNO₈
M_r	521.98
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	13.8720 (8), 16.5110 (11), 22.8120 (16)
V (Å³)	5224.9 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.30 × 0.27 × 0.25

Data collection
Diffractometer	MacScience DIPLabo 32001 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8214, 4464, 3146
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.186, 1.05
No. of reflections	4464
No. of parameters	332
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.39

Computer programs: XPRESS (MacScience, 2002), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and ORTEPII (Johnson, 1976), PLATON (Spek, 2009).

Acknowledgements

The authors are grateful to the DST and Government of India project SP/I2/FOO/93 and the University of Mysore for financial assistance.

References

Baliah, V., Jeyaraman, R. & Chandrashekaran, L. (1983). Chem. Rev. 83, 379—423. CrossRef Web of Science Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Ganellin, C. R. & Spickett, R. G. (1965). J. Med. Chem. 8, 619–625. CrossRef CAS PubMed Web of Science Google Scholar
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
MacScience (2002). XPRESS. MacScience Co. Ltd, Yokohama, Japan. Google Scholar
Mobio, I. G., Soldatenkov, A. T., Federov, V. O., Ageev, E. A., Sergeeva, N. D., Lin, S., Stashenko, E. E., Prostakov, N. S. & Andreeva, E. I. (1989). Khim. Farm. Zh. 23, 421–427. CAS Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Prostakov, N. S. & Gaivoronskaya, L. A. (1978). Russ. Chem. Rev. 47, 447—469. CrossRef 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

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.