1-Dichloro­acetyl-r-2,c-6-bis­(4-methoxy­phen­yl)-t-3-methyl­piperidin-4-one

Ravichandran, K.; Ramesh, P.; Sakthivel, P.; Ponnuswamy, S.; Ponnuswamy, M.N.

doi:10.1107/S1600536809054713

organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o262

https://doi.org/10.1107/S1600536809054713

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1-Dichloroacetyl-r-2,c-6-bis(4-methoxyphenyl)-t-3-methylpiperidin-4-one

K. Ravichandran,^a P. Ramesh,^a P. Sakthivel,^b S. Ponnuswamy ^b and M. N. Ponnuswamy ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Chemistry, Government Arts College (Autonomous), Coimbatore 641 018, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 17 December 2009; accepted 19 December 2009; online 9 January 2010)

In the title compound, C₂₂H₂₃Cl₂NO₄, the piperidine ring adopts a distorted boat conformation. The methoxy groups lie in the plane of the benzene rings to which they are attached. The benzene rings are oriented at angles of 84.3 (1) and 76.8 (1)° with respect to the best plane through the piperidine ring. The crystal packing is stabilized by intermolecular C—H⋯O interactions.

Related literature

For general background to piperidine derivatives, see: Perumal et al. (2001 ); Dimmock et al. (2001 ). For asymmetry parameters, see: Nardelli (1983 ). For puckering parameters, see: Cremer & Pople (1975 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₂H₂₃Cl₂NO₄
M_r = 436.31
Monoclinic, P 2₁ /c
a = 19.3021 (16) Å
b = 10.5886 (9) Å
c = 10.3241 (10) Å
β = 91.445 (5)°
V = 2109.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 293 K
0.25 × 0.24 × 0.23 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.919, T_max = 0.926
17272 measured reflections
5140 independent reflections
2632 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.210
S = 1.05
5140 reflections
265 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1ⁱ	0.98	2.31	3.264 (4)	164
C8—H8⋯O1ⁱ	0.98	2.52	3.363 (4)	144
C18—H18⋯O1ⁱ	0.93	2.57	3.391 (4)	147
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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: https://doi.org/10.1107/S1600536809054713/bt5145sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809054713/bt5145Isup2.hkl

checkCIF report

Comment top

Piperidine derivatives are the valued heterocyclic compounds in the field of medicinal chemistry. piperidin-4-ones are reported to possess analgesic, anti-inflammatory, central nervous system (CNS), local anaesthetic, anticancer and antimicrobial activity (Perumal et al. (2001); Dimmock et al., 2001). The crystallographic study of the title compound has been carried out to establish the molecular structure

The ORTEP diagram of the title compound is shown in Fig.1. The piperidine ring in the molecule adopts a distorted boat conformation with the puckering parameters (Cremer & Pople, 1975) and the asymmetry parameters (Nardelli, 1983) are: q₂ = 0.685 (3) Å, q₃ = 0.039 (3) Å, φ₂ = 72.1 (3)° and Δ_s(C2 & C5)= 14.9 (3)°. The methoxy groups lie in the plane of phenyl rings and these phenyl rings are oriented at angles of 84.3 (1)° and 76.8 (1)° with best plane of piperidine ring.The sum of the bond angles around the atom N1(359.7°) of the piperidine ring in the molecule is in accordance with sp² hybridization.

The crystal packing is stabilized by C—H···O types of intra and intermolecular interactions, which link the molecules into a chain extending along the c axis. Atoms C6, C18 and C4 of the molecule at (x, y, z) donate a proton to trifurcated acceptor atom O1 of the molecule at (x, 1/2 - y, -1/2 + z). Intermolecular interactions C6—H6···O1 and C18—H18···O1 form C5 & C7 zigzag chains (Bernstein et al., 1995), whereas the other interaction C8—H8···O1 forms a C4 one-dimensional chain, running along the c axis, as shown in Fig. 2.

Related literature top

For general background to piperidine derivatives, see: Perumal et al. (2001); Dimmock et al. (2001). For asymmetry parameters, see: Nardelli (1983). For puckering parameters, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

To a solution of r-2,c-6-bis(4-methoxyphenyl)-t-3-methylpiperidin-4-one (1.625 g) in anhydrous benzene (60 ml) was added triethylamine (2.1 ml) and dichloroacetylchloride (1.42 ml). The reaction mixture was allowed to stirr at room teperature for 2hrs. The resulting solution was washed with sodium bicarbonate solution (10%) and water. The organic layer was dried over anhydrous sodium sulfate, evaporated and crystallized from benzene: pet-ether (60–80°C) in the ratio of 9:1.

Structure description top

For general background to piperidine derivatives, see: Perumal et al. (2001); Dimmock et al. (2001). For asymmetry parameters, see: Nardelli (1983). For puckering parameters, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

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. H atoms have been omitted for clarity.
	Fig. 2. The crystal packing of the molecules viewed down a–axis. H atoms not involved in hydrogen bonding have been omitted for clarity.

1-Dichloroacetyl-r-2,c-6-bis(4-methoxyphenyl)-t- 3-methylpiperidin-4-one top

Crystal data top

C₂₂H₂₃Cl₂NO₄	F(000) = 912
M_r = 436.31	D_x = 1.374 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2564 reflections
a = 19.3021 (16) Å	θ = 1.1–28.7°
b = 10.5886 (9) Å	µ = 0.34 mm⁻¹
c = 10.3241 (10) Å	T = 293 K
β = 91.445 (5)°	Block, colorless
V = 2109.4 (3) Å³	0.25 × 0.24 × 0.23 mm
Z = 4

Data collection top

Bruker SMART APEXII area-detector diffractometer	5140 independent reflections
Radiation source: fine-focus sealed tube	2632 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ω and φ scans	θ_max = 28.7°, θ_min = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −25→25
T_min = 0.919, T_max = 0.926	k = −13→14
17272 measured reflections	l = −13→10

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.210	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.1035P)² + 0.3613P] where P = (F_o² + 2F_c²)/3
5140 reflections	(Δ/σ)_max = 0.001
265 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₂₂H₂₃Cl₂NO₄	V = 2109.4 (3) Å³
M_r = 436.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 19.3021 (16) Å	µ = 0.34 mm⁻¹
b = 10.5886 (9) Å	T = 293 K
c = 10.3241 (10) Å	0.25 × 0.24 × 0.23 mm
β = 91.445 (5)°

Data collection top

Bruker SMART APEXII area-detector diffractometer	5140 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2632 reflections with I > 2σ(I)
T_min = 0.919, T_max = 0.926	R_int = 0.050
17272 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.210	H-atom parameters constrained
S = 1.05	Δρ_max = 0.37 e Å⁻³
5140 reflections	Δρ_min = −0.34 e Å⁻³
265 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
Cl1	0.06236 (4)	0.37763 (8)	0.02208 (10)	0.0600 (3)
Cl2	0.10261 (5)	0.12850 (8)	−0.06850 (10)	0.0618 (3)
O1	0.18680 (12)	0.2296 (2)	0.1496 (2)	0.0611 (7)
O2	0.37098 (13)	0.6870 (3)	0.4740 (3)	0.0714 (8)
O3	0.43242 (15)	0.3729 (4)	−0.1711 (4)	0.1125 (13)
O4	0.06912 (12)	0.8442 (2)	−0.1071 (3)	0.0607 (7)
N1	0.24905 (12)	0.3470 (2)	0.0117 (2)	0.0378 (6)
C2	0.31270 (15)	0.3183 (3)	0.0888 (3)	0.0433 (8)
H2	0.3025	0.2422	0.1388	0.052*
C3	0.36826 (17)	0.2806 (3)	−0.0059 (4)	0.0568 (9)
H3A	0.4110	0.2633	0.0423	0.068*
H3B	0.3541	0.2032	−0.0493	0.068*
C4	0.38194 (18)	0.3784 (4)	−0.1054 (4)	0.0617 (10)
C5	0.32820 (16)	0.4799 (3)	−0.1204 (3)	0.0481 (8)
H5	0.3364	0.5402	−0.0496	0.058*
C6	0.25383 (14)	0.4284 (3)	−0.1064 (3)	0.0379 (7)
H6	0.2431	0.3755	−0.1821	0.046*
C7	0.19106 (15)	0.2871 (3)	0.0469 (3)	0.0407 (7)
C8	0.12870 (15)	0.2872 (3)	−0.0465 (3)	0.0413 (7)
H8	0.1416	0.3238	−0.1297	0.050*
C9	0.33116 (14)	0.4193 (3)	0.1869 (3)	0.0424 (7)
C10	0.28014 (16)	0.4676 (3)	0.2662 (3)	0.0502 (8)
H10	0.2348	0.4393	0.2548	0.060*
C11	0.29471 (17)	0.5556 (4)	0.3605 (3)	0.0562 (9)
H11	0.2595	0.5863	0.4117	0.067*
C12	0.36200 (18)	0.5987 (3)	0.3792 (3)	0.0530 (9)
C13	0.41367 (17)	0.5519 (4)	0.3030 (4)	0.0584 (10)
H13	0.4591	0.5795	0.3151	0.070*
C14	0.39748 (16)	0.4635 (4)	0.2082 (3)	0.0543 (9)
H14	0.4327	0.4328	0.1571	0.065*
C15	0.4393 (2)	0.7283 (4)	0.5030 (5)	0.0878 (14)
H15A	0.4678	0.6569	0.5255	0.132*
H15B	0.4389	0.7863	0.5744	0.132*
H15C	0.4577	0.7698	0.4286	0.132*
C16	0.3347 (2)	0.5526 (4)	−0.2460 (4)	0.0691 (11)
H16A	0.3821	0.5770	−0.2566	0.104*
H16B	0.3061	0.6267	−0.2436	0.104*
H16C	0.3199	0.5001	−0.3173	0.104*
C17	0.20227 (14)	0.5359 (3)	−0.1064 (3)	0.0348 (7)
C18	0.15426 (15)	0.5514 (3)	−0.2067 (3)	0.0399 (7)
H18	0.1529	0.4928	−0.2738	0.048*
C19	0.10828 (16)	0.6511 (3)	−0.2103 (3)	0.0428 (7)
H19	0.0759	0.6581	−0.2781	0.051*
C20	0.11057 (16)	0.7406 (3)	−0.1126 (3)	0.0425 (7)
C21	0.15861 (16)	0.7270 (3)	−0.0128 (3)	0.0456 (8)
H21	0.1608	0.7871	0.0528	0.055*
C22	0.20341 (16)	0.6263 (3)	−0.0083 (3)	0.0419 (7)
H22	0.2348	0.6183	0.0610	0.050*
C23	0.0234 (2)	0.8678 (3)	−0.2145 (5)	0.0703 (11)
H23A	0.0497	0.8761	−0.2917	0.105*
H23B	−0.0018	0.9444	−0.1999	0.105*
H23C	−0.0085	0.7987	−0.2243	0.105*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0590 (5)	0.0573 (5)	0.0641 (7)	0.0081 (4)	0.0103 (4)	0.0020 (4)
Cl2	0.0749 (6)	0.0441 (5)	0.0665 (7)	−0.0149 (4)	0.0003 (5)	−0.0053 (4)
O1	0.0674 (15)	0.0703 (16)	0.0452 (15)	−0.0148 (12)	−0.0051 (12)	0.0270 (13)
O2	0.0731 (17)	0.0837 (18)	0.0570 (18)	−0.0107 (14)	−0.0054 (14)	−0.0164 (15)
O3	0.0646 (18)	0.161 (3)	0.114 (3)	0.0281 (19)	0.0481 (19)	0.042 (2)
O4	0.0657 (15)	0.0398 (12)	0.076 (2)	0.0079 (11)	−0.0022 (14)	−0.0061 (12)
N1	0.0424 (13)	0.0422 (14)	0.0288 (15)	0.0000 (11)	0.0011 (11)	0.0049 (11)
C2	0.0434 (17)	0.0500 (18)	0.037 (2)	0.0071 (14)	−0.0012 (14)	0.0052 (15)
C3	0.0512 (19)	0.068 (2)	0.051 (2)	0.0129 (17)	0.0018 (16)	−0.0085 (19)
C4	0.0458 (19)	0.088 (3)	0.052 (2)	−0.0024 (18)	0.0091 (17)	−0.006 (2)
C5	0.0497 (18)	0.058 (2)	0.037 (2)	−0.0090 (15)	0.0100 (14)	−0.0009 (16)
C6	0.0457 (16)	0.0459 (17)	0.0223 (16)	−0.0058 (13)	0.0028 (12)	−0.0004 (13)
C7	0.0467 (17)	0.0386 (16)	0.0367 (19)	−0.0007 (13)	0.0002 (14)	0.0030 (14)
C8	0.0463 (16)	0.0394 (15)	0.0382 (19)	−0.0059 (13)	0.0011 (14)	0.0018 (13)
C9	0.0397 (16)	0.0568 (19)	0.0307 (18)	0.0009 (14)	−0.0018 (13)	0.0029 (15)
C10	0.0420 (17)	0.068 (2)	0.041 (2)	−0.0006 (15)	−0.0010 (14)	−0.0059 (17)
C11	0.0478 (19)	0.077 (2)	0.043 (2)	0.0032 (17)	0.0017 (15)	−0.0102 (19)
C12	0.060 (2)	0.065 (2)	0.033 (2)	−0.0035 (17)	−0.0043 (16)	−0.0014 (17)
C13	0.0459 (19)	0.083 (3)	0.046 (2)	−0.0115 (18)	−0.0030 (16)	0.001 (2)
C14	0.0411 (17)	0.083 (3)	0.038 (2)	−0.0005 (17)	0.0037 (14)	−0.0004 (19)
C15	0.086 (3)	0.098 (3)	0.078 (3)	−0.025 (3)	−0.013 (3)	−0.022 (3)
C16	0.079 (3)	0.078 (3)	0.051 (3)	−0.019 (2)	0.019 (2)	0.010 (2)
C17	0.0474 (16)	0.0344 (15)	0.0228 (16)	−0.0052 (12)	0.0054 (12)	0.0021 (12)
C18	0.0579 (18)	0.0344 (15)	0.0276 (18)	−0.0022 (13)	0.0029 (14)	−0.0015 (13)
C19	0.0543 (18)	0.0383 (16)	0.0356 (19)	−0.0048 (13)	−0.0026 (14)	0.0099 (14)
C20	0.0512 (17)	0.0336 (16)	0.043 (2)	−0.0036 (13)	0.0078 (15)	0.0030 (14)
C21	0.0567 (18)	0.0443 (17)	0.036 (2)	−0.0033 (15)	0.0074 (15)	−0.0106 (15)
C22	0.0478 (17)	0.0485 (18)	0.0294 (18)	−0.0010 (14)	−0.0010 (13)	−0.0004 (14)
C23	0.068 (2)	0.051 (2)	0.090 (3)	0.0093 (18)	−0.012 (2)	0.014 (2)

Geometric parameters (Å, º) top

Cl1—C8	1.762 (3)	C10—C11	1.372 (5)
Cl2—C8	1.768 (3)	C10—H10	0.9300
O1—C7	1.228 (4)	C11—C12	1.385 (4)
O2—C12	1.362 (4)	C11—H11	0.9300
O2—C15	1.415 (4)	C12—C13	1.378 (5)
O3—C4	1.203 (4)	C13—C14	1.383 (5)
O4—C20	1.360 (4)	C13—H13	0.9300
O4—C23	1.422 (4)	C14—H14	0.9300
N1—C7	1.344 (4)	C15—H15A	0.9600
N1—C2	1.479 (4)	C15—H15B	0.9600
N1—C6	1.498 (4)	C15—H15C	0.9600
C2—C9	1.509 (4)	C16—H16A	0.9600
C2—C3	1.523 (4)	C16—H16B	0.9600
C2—H2	0.9800	C16—H16C	0.9600
C3—C4	1.487 (5)	C17—C18	1.382 (4)
C3—H3A	0.9700	C17—C22	1.394 (4)
C3—H3B	0.9700	C18—C19	1.379 (4)
C4—C5	1.499 (5)	C18—H18	0.9300
C5—C16	1.516 (5)	C19—C20	1.384 (4)
C5—C6	1.546 (4)	C19—H19	0.9300
C5—H5	0.9800	C20—C21	1.377 (4)
C6—C17	1.512 (4)	C21—C22	1.372 (4)
C6—H6	0.9800	C21—H21	0.9300
C7—C8	1.523 (4)	C22—H22	0.9300
C8—H8	0.9800	C23—H23A	0.9600
C9—C14	1.375 (4)	C23—H23B	0.9600
C9—C10	1.393 (4)	C23—H23C	0.9600

C12—O2—C15	117.7 (3)	C10—C11—H11	120.1
C20—O4—C23	117.6 (3)	C12—C11—H11	120.1
C7—N1—C2	116.4 (2)	O2—C12—C13	125.2 (3)
C7—N1—C6	124.0 (2)	O2—C12—C11	115.3 (3)
C2—N1—C6	119.3 (2)	C13—C12—C11	119.4 (3)
N1—C2—C9	113.3 (2)	C12—C13—C14	119.5 (3)
N1—C2—C3	107.3 (3)	C12—C13—H13	120.2
C9—C2—C3	117.3 (3)	C14—C13—H13	120.2
N1—C2—H2	106.1	C9—C14—C13	122.4 (3)
C9—C2—H2	106.1	C9—C14—H14	118.8
C3—C2—H2	106.1	C13—C14—H14	118.8
C4—C3—C2	113.6 (3)	O2—C15—H15A	109.5
C4—C3—H3A	108.8	O2—C15—H15B	109.5
C2—C3—H3A	108.8	H15A—C15—H15B	109.5
C4—C3—H3B	108.8	O2—C15—H15C	109.5
C2—C3—H3B	108.8	H15A—C15—H15C	109.5
H3A—C3—H3B	107.7	H15B—C15—H15C	109.5
O3—C4—C3	121.1 (4)	C5—C16—H16A	109.5
O3—C4—C5	123.0 (4)	C5—C16—H16B	109.5
C3—C4—C5	115.9 (3)	H16A—C16—H16B	109.5
C4—C5—C16	112.4 (3)	C5—C16—H16C	109.5
C4—C5—C6	112.3 (3)	H16A—C16—H16C	109.5
C16—C5—C6	110.9 (3)	H16B—C16—H16C	109.5
C4—C5—H5	107.0	C18—C17—C22	117.5 (3)
C16—C5—H5	107.0	C18—C17—C6	121.2 (3)
C6—C5—H5	107.0	C22—C17—C6	121.3 (3)
N1—C6—C17	112.3 (2)	C19—C18—C17	122.0 (3)
N1—C6—C5	110.8 (2)	C19—C18—H18	119.0
C17—C6—C5	110.3 (2)	C17—C18—H18	119.0
N1—C6—H6	107.7	C18—C19—C20	119.7 (3)
C17—C6—H6	107.7	C18—C19—H19	120.1
C5—C6—H6	107.7	C20—C19—H19	120.1
O1—C7—N1	122.8 (3)	O4—C20—C21	116.0 (3)
O1—C7—C8	118.6 (3)	O4—C20—C19	125.1 (3)
N1—C7—C8	118.6 (3)	C21—C20—C19	118.9 (3)
C7—C8—Cl1	108.5 (2)	C22—C21—C20	121.3 (3)
C7—C8—Cl2	107.4 (2)	C22—C21—H21	119.4
Cl1—C8—Cl2	111.14 (16)	C20—C21—H21	119.4
C7—C8—H8	109.9	C21—C22—C17	120.7 (3)
Cl1—C8—H8	109.9	C21—C22—H22	119.7
Cl2—C8—H8	109.9	C17—C22—H22	119.7
C14—C9—C10	116.7 (3)	O4—C23—H23A	109.5
C14—C9—C2	123.5 (3)	O4—C23—H23B	109.5
C10—C9—C2	119.7 (3)	H23A—C23—H23B	109.5
C11—C10—C9	122.1 (3)	O4—C23—H23C	109.5
C11—C10—H10	119.0	H23A—C23—H23C	109.5
C9—C10—H10	119.0	H23B—C23—H23C	109.5
C10—C11—C12	119.8 (3)

C7—N1—C2—C9	−101.3 (3)	N1—C2—C9—C10	46.9 (4)
C6—N1—C2—C9	84.8 (3)	C3—C2—C9—C10	172.8 (3)
C7—N1—C2—C3	127.6 (3)	C14—C9—C10—C11	0.5 (5)
C6—N1—C2—C3	−46.3 (3)	C2—C9—C10—C11	177.3 (3)
N1—C2—C3—C4	57.2 (4)	C9—C10—C11—C12	−0.2 (6)
C9—C2—C3—C4	−71.6 (4)	C15—O2—C12—C13	−4.4 (6)
C2—C3—C4—O3	166.1 (4)	C15—O2—C12—C11	176.0 (3)
C2—C3—C4—C5	−15.7 (4)	C10—C11—C12—O2	179.3 (3)
O3—C4—C5—C16	14.5 (5)	C10—C11—C12—C13	−0.3 (6)
C3—C4—C5—C16	−163.6 (3)	O2—C12—C13—C14	−179.0 (3)
O3—C4—C5—C6	140.2 (4)	C11—C12—C13—C14	0.6 (6)
C3—C4—C5—C6	−37.8 (4)	C10—C9—C14—C13	−0.2 (5)
C7—N1—C6—C17	57.7 (4)	C2—C9—C14—C13	−176.9 (3)
C2—N1—C6—C17	−128.9 (3)	C12—C13—C14—C9	−0.3 (6)
C7—N1—C6—C5	−178.4 (3)	N1—C6—C17—C18	−122.7 (3)
C2—N1—C6—C5	−5.1 (4)	C5—C6—C17—C18	113.1 (3)
C4—C5—C6—N1	48.3 (4)	N1—C6—C17—C22	60.2 (3)
C16—C5—C6—N1	174.9 (3)	C5—C6—C17—C22	−64.0 (3)
C4—C5—C6—C17	173.3 (3)	C22—C17—C18—C19	−0.8 (4)
C16—C5—C6—C17	−60.1 (3)	C6—C17—C18—C19	−178.0 (3)
C2—N1—C7—O1	12.7 (4)	C17—C18—C19—C20	1.4 (4)
C6—N1—C7—O1	−173.7 (3)	C23—O4—C20—C21	174.2 (3)
C2—N1—C7—C8	−165.4 (3)	C23—O4—C20—C19	−5.0 (4)
C6—N1—C7—C8	8.2 (4)	C18—C19—C20—O4	178.5 (3)
O1—C7—C8—Cl1	69.3 (3)	C18—C19—C20—C21	−0.7 (4)
N1—C7—C8—Cl1	−112.5 (3)	O4—C20—C21—C22	−179.8 (3)
O1—C7—C8—Cl2	−50.9 (3)	C19—C20—C21—C22	−0.6 (4)
N1—C7—C8—Cl2	127.3 (3)	C20—C21—C22—C17	1.2 (4)
N1—C2—C9—C14	−136.5 (3)	C18—C17—C22—C21	−0.5 (4)
C3—C2—C9—C14	−10.6 (5)	C6—C17—C22—C21	176.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ⁱ	0.98	2.31	3.264 (4)	164
C8—H8···O1ⁱ	0.98	2.52	3.363 (4)	144
C18—H18···O1ⁱ	0.93	2.57	3.391 (4)	147

Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₃Cl₂NO₄
M_r	436.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	19.3021 (16), 10.5886 (9), 10.3241 (10)
β (°)	91.445 (5)
V (Å³)	2109.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.25 × 0.24 × 0.23

Data collection
Diffractometer	Bruker SMART APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.919, 0.926
No. of measured, independent and observed [I > 2σ(I)] reflections	17272, 5140, 2632
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.675

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.210, 1.05
No. of reflections	5140
No. of parameters	265
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.34

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
C6—H6···O1ⁱ	0.98	2.31	3.264 (4)	163.9
C8—H8···O1ⁱ	0.98	2.52	3.363 (4)	143.5
C18—H18···O1ⁱ	0.93	2.57	3.391 (4)	146.8

Symmetry code: (i) x, −y+1/2, z−1/2.

Acknowledgements

KR thanks the GNR X-ray Facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection and the management of Kandaswami Kandar's College, Velur, Namakkal, TN, India, for the encouragement to pursue the programme.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science 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
Dimmock, J. R., Padmanilayam, M. P., Puthucode, R. N., Nazarali, A. J., Motaganahalli, N. L., Zello, G. A., Quail, J. W., Oloo, E. O., Kraatz, H. B., Prisciak, J. S., Allen, T. M., Santhos, C. L., Balsarini, J., Clercq, E. D. & Manavathu, E. K. (2001). J. Med. Chem. 44, 586–593. Web of Science CSD CrossRef PubMed CAS 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
Perumal, R. V., Adiraj, M. & Shanmugapandiyan, P. (2001). Indian Drugs, 38, 156–159 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