1-Chloro­acetyl-2,6-bis­(2-methoxy­phen­yl)-3,5-dimethyl­piperidin-4-one

Aridoss, G.; Gayathri, D.; Velmurugan, D.; Kim, M.S.; Jeong, Y.T.

doi:10.1107/S1600536809033674

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 9| September 2009| Pages o2276-o2277

doi:10.1107/S1600536809033674

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1-Chloroacetyl-2,6-bis(2-methoxyphenyl)-3,5-dimethylpiperidin-4-one

G. Aridoss,^a D. Gayathri,^b ‡ D. Velmurugan,^b M. S. Kim ^a and Yeon Tae Jeong ^a ^*

^aDivision of Image Science and Information 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 17 August 2009; accepted 24 August 2009; online 29 August 2009)

The piperidone ring in the title compound, C₂₃H₂₆ClNO₄, adopts a boat conformation with its two out-of-plane C atoms deviating by 0.597 (2) and 0.630 (2) Å from the least-squares plane of the rest of atoms in the ring. The two aromatic rings are roughly perpendicular to each other, making a dihedral angle of 75.1 (1)°, and a C—H⋯π intramolecular interaction is observed. The crystal packing is stabilized by a C—H⋯O intermolecular interaction, generating a chain with a C(9) motif along the a axis.

Related literature

For the biological activity of the piperidine nucleus, see: Weintraub et al. (2003 ). For the biological activity of piperidones and their N-acyl derivatives, see: Perumal et al. (2001 ); Weintraub et al. (2003); Aridoss et al. (2008 , 2009 ); Aridoss, Balasubramanian, Parthiban, Ramachandran & Kabilan (2007 ). For a related structure, see: Ramachandran et al. (2008 ). For the synthesis, see: Aridoss, Balasubramanian, Parthiban & Kabilan (2007 ). For ring conformational analysis, see: Cremer & Pople (1975 ); Nardelli (1983 ).

Experimental

Crystal data

C₂₃H₂₆ClNO₄
M_r = 415.90
Triclinic, $[P \overline 1]$
a = 8.9921 (6) Å
b = 11.3725 (8) Å
c = 11.9373 (8) Å
α = 71.630 (1)°
β = 68.465 (1)°
γ = 72.903 (1)°
V = 1055.45 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 293 K
0.27 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: none
11114 measured reflections
4603 independent reflections
4054 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.145
S = 1.05
4603 reflections
266 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C23—H23C⋯O1ⁱ	0.96	2.50	3.321 (3)	144
C9—H9⋯Cg	0.93	2.69	3.621 (2)	177
Symmetry code: (i) x+1, y, z. Cg is the centroid of the C17–C22 ring.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809033674/is2452sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809033674/is2452Isup2.hkl

checkCIF report

Comment top

Nitrogen containing heterocycles possess important biological profiles. For instance, the piperidine sub-structure is ubiquitous structural feature of many alkaloids, natural products and drug candidates (Weintraub et al., 2003). During the last decade, there were thousands of piperidine compounds mentioned in clinical and preclinical studies. As well owing to the relevance of piperidone-containing bioactive compounds, synthesis of piperidone derivatives have also attracted considerable attention among chemists and biologist (Perumal et al., 2001). It has been recognized well by our earlier studies that N-chloroacetyl and the further functionalized derivatives of 2,6-diarylpiperidin-4-one showed moderate to good antimicrobial, analgesic, antipyretic and antimycobacterial activities (Aridoss, Balasubramanian, Parthiban, Ramachandran & Kabilan, 2007; Aridoss et al., 2008,2009). As an extension to our studies on stereochemistry (Aridoss, Balasubramanian, Parthiban & Kabilan, 2007) and crystal studies (Ramachandran et al., 2008), we report here the X-ray crystallographic study of 1-chloroacetyl-2,6-bis (2-methoxyphenyl)-3,5-dimethylpiperidin-4-one.

The molecular structure of the title compound (I) is shown in Fig.1. The sum of the angles at N1 (358.9 (3)°) is in accordance with sp² hybridization. The two phenyl rings in the title compound (I) are nearly perpendicular with the dihedral angle being 75.1 (1)°. Methoxy group attached to the phenyl rings is planar as evident from the torsion angle [(C14—O2—C13—C12 (-3.7 (3)°) and C23—O4—C22—C21 (-1.4 (2)°)]. The torsion angle around O1—C6—C7—Cl1 [0.0 (2)°] indicates the planarity of chloroacetyl moiety. The piperidone ring in the title compound (I) adopts boat conformation with atoms C2 and C5 deviating by -0.597 (2) and -0.630 (2) Å, respectively, from the least-squares plane defined by rest of the atoms (N1/C1/C3/C4) in the ring. The puckering parameters (Cremer & Pople, 1975) and the smallest displacement asymmetry parameters (Nardelli, 1983) for piperidone ring are q₂ = 0.709 (2) Å, q₃ = 0.022 (2) Å; Q_T = 0.710 (2) Å and θ = 88.3 (1)°.

The molecule of (I) is stabilized by weak C—H···O and C—H···π intramolecular interactions. In C—H···π intramolecular interaction, atom C9 acts as donor to the centroid (Cg) of the phenyl ring C17–C22 with H···Cg distance of 2.69 Å. The crystal packing is stabilized by C—H···O intermolecular interaction, wherein atom C23 acts as donor to O1 (1 + x, y, z) generating a chain C(9) along the a axis.

Related literature top

For the biological activity of the piperidine nucleus, see: Weintraub et al. (2003). For the biological activity of piperidones and their N-acyl derivatives, see: Perumal et al. (2001); Weintraub et al. (2003); Aridoss et al. (2008, 2009); Aridoss, Balasubramanian, Parthiban, Ramachandran & Kabilan (2007). For a related structure, see: Ramachandran et al. (2008). For the synthesis, see: Aridoss, Balasubramanian, Parthiban & Kabilan (2007). For ring conformational analysis, see: Cremer & Pople (1975); Nardelli (1983). Cg is the centroid of the C17–C22 ring.

Experimental top

The title compound was obtained by adopting our earlier method (Aridoss, Balasubramanian, Parthiban & Kabilan, 2007). To a solution of 2,6-bis(2- methoxyphenyl)-3,5-dimethylpiperidin-4-one (1 equiv.) and NEt₃ (1.5 equiv.) in freshly distilled benzene, chloroacetyl chloride (1 equiv.) in benzene was added in drop wise. Stirring was continued until the completion of reaction. Later, it was poured into water and extracted with ethyl acetate. The combined organic extracts was then washed well with 3% sodium bicarbonate solution, brine and dried over anhydrous sodium sulfate. This upon evaporation and subsequent recrystallization of title compound in distilled ethanol afforded fine white crystals suitable for X-ray diffraction study.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PARST (Nardelli, 1995).

Figures top

	Fig. 1. The molecular structure of title compound, (I), showing 30% probability displacement ellipsoids.
	Fig. 2. The molecular packing of (I), showing intramolecular C—H···π and intermolecular C—H···O interactions. For clarity, hydrogen atoms which are not involved in hydrogen bonding are omitted.

1-Chloroacetyl-2,6-bis(2-methoxyphenyl)-3,5-dimethylpiperidin-4-one top

Crystal data top

C₂₃H₂₆ClNO₄	Z = 2
M_r = 415.90	F(000) = 440
Triclinic, P1	D_x = 1.309 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9921 (6) Å	Cell parameters from 3104 reflections
b = 11.3725 (8) Å	θ = 1.9–28.0°
c = 11.9373 (8) Å	µ = 0.21 mm⁻¹
α = 71.630 (1)°	T = 293 K
β = 68.465 (1)°	Block, colourless
γ = 72.903 (1)°	0.27 × 0.22 × 0.20 mm
V = 1055.45 (12) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4054 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.026
Graphite monochromator	θ_max = 28.0°, θ_min = 1.9°
ω scans	h = −11→11
11114 measured reflections	k = −15→14
4603 independent reflections	l = −15→15

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.145	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0778P)² + 0.248P] where P = (F_o² + 2F_c²)/3
4603 reflections	(Δ/σ)_max < 0.001
266 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₃H₂₆ClNO₄	γ = 72.903 (1)°
M_r = 415.90	V = 1055.45 (12) Å³
Triclinic, P1	Z = 2
a = 8.9921 (6) Å	Mo Kα radiation
b = 11.3725 (8) Å	µ = 0.21 mm⁻¹
c = 11.9373 (8) Å	T = 293 K
α = 71.630 (1)°	0.27 × 0.22 × 0.20 mm
β = 68.465 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4054 reflections with I > 2σ(I)
11114 measured reflections	R_int = 0.026
4603 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.145	H-atom parameters constrained
S = 1.05	Δρ_max = 0.27 e Å⁻³
4603 reflections	Δρ_min = −0.35 e Å⁻³
266 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	0.62492 (17)	0.76769 (12)	0.18450 (12)	0.0365 (3)
H1	0.5887	0.7813	0.1125	0.044*
C2	0.75304 (18)	0.84927 (13)	0.14741 (13)	0.0409 (3)
H2	0.7983	0.8264	0.2164	0.049*
C3	0.6724 (2)	0.98870 (15)	0.13142 (15)	0.0493 (4)
C4	0.51873 (19)	1.02296 (13)	0.23286 (14)	0.0435 (3)
H4	0.5333	1.0870	0.2648	0.052*
C5	0.47941 (17)	0.90843 (12)	0.34028 (13)	0.0376 (3)
H5	0.3655	0.9344	0.3879	0.045*
C6	0.33625 (18)	0.76953 (14)	0.31911 (14)	0.0415 (3)
C7	0.3312 (2)	0.6876 (2)	0.2420 (2)	0.0677 (5)
H7A	0.4139	0.6108	0.2494	0.081*
H7B	0.3572	0.7327	0.1556	0.081*
C8	0.70453 (17)	0.62802 (13)	0.21844 (13)	0.0391 (3)
C9	0.7535 (2)	0.57969 (14)	0.32461 (14)	0.0457 (3)
H9	0.7322	0.6323	0.3769	0.055*
C10	0.8335 (2)	0.45490 (16)	0.35465 (17)	0.0557 (4)
H10	0.8653	0.4242	0.4261	0.067*
C11	0.8647 (2)	0.37779 (16)	0.27738 (19)	0.0609 (5)
H11	0.9186	0.2942	0.2968	0.073*
C12	0.8177 (2)	0.42187 (16)	0.17127 (19)	0.0591 (4)
H12	0.8392	0.3681	0.1201	0.071*
C13	0.73780 (19)	0.54777 (15)	0.14083 (15)	0.0465 (3)
C14	0.7241 (3)	0.5234 (2)	−0.0467 (2)	0.0764 (6)
H14A	0.8404	0.4997	−0.0800	0.115*
H14B	0.6782	0.5702	−0.1128	0.115*
H14C	0.6792	0.4486	−0.0045	0.115*
C15	0.8945 (2)	0.82148 (18)	0.03379 (16)	0.0550 (4)
H15A	0.8536	0.8374	−0.0345	0.083*
H15B	0.9488	0.7345	0.0516	0.083*
H15C	0.9704	0.8751	0.0128	0.083*
C16	0.3767 (2)	1.08034 (17)	0.17668 (17)	0.0568 (4)
H16A	0.4010	1.1535	0.1113	0.085*
H16B	0.2784	1.1045	0.2397	0.085*
H16C	0.3621	1.0188	0.1440	0.085*
C17	0.57351 (18)	0.85534 (13)	0.43542 (13)	0.0380 (3)
C18	0.51132 (19)	0.76226 (14)	0.53789 (13)	0.0431 (3)
H18	0.4129	0.7432	0.5475	0.052*
C19	0.5920 (2)	0.69789 (16)	0.62510 (15)	0.0516 (4)
H19	0.5477	0.6372	0.6930	0.062*
C20	0.7387 (2)	0.72462 (17)	0.61039 (16)	0.0541 (4)
H20	0.7966	0.6782	0.6662	0.065*
C21	0.8006 (2)	0.81951 (16)	0.51375 (15)	0.0491 (4)
H21	0.8982	0.8386	0.5060	0.059*
C22	0.71660 (18)	0.88681 (13)	0.42754 (13)	0.0400 (3)
C23	0.9135 (3)	1.0185 (2)	0.3189 (2)	0.0691 (5)
H23A	0.9001	1.0448	0.3915	0.104*
H23B	0.9348	1.0872	0.2475	0.104*
H23C	1.0034	0.9479	0.3092	0.104*
N1	0.48009 (14)	0.80640 (11)	0.28696 (11)	0.0365 (3)
O1	0.21671 (13)	0.80127 (12)	0.40297 (11)	0.0529 (3)
O2	0.68636 (18)	0.59924 (13)	0.03773 (12)	0.0640 (4)
O3	0.7251 (2)	1.06760 (13)	0.04061 (15)	0.0806 (5)
O4	0.76967 (14)	0.98287 (11)	0.33137 (11)	0.0502 (3)
Cl1	0.14021 (6)	0.64709 (5)	0.28760 (5)	0.06999 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0373 (7)	0.0359 (6)	0.0342 (6)	−0.0015 (5)	−0.0113 (5)	−0.0103 (5)
C2	0.0401 (7)	0.0400 (7)	0.0398 (7)	−0.0062 (6)	−0.0100 (6)	−0.0097 (5)
C3	0.0534 (9)	0.0401 (7)	0.0506 (8)	−0.0103 (7)	−0.0156 (7)	−0.0050 (6)
C4	0.0497 (8)	0.0330 (6)	0.0496 (8)	−0.0015 (6)	−0.0221 (7)	−0.0102 (6)
C5	0.0380 (7)	0.0351 (6)	0.0411 (7)	0.0000 (5)	−0.0148 (6)	−0.0141 (5)
C6	0.0367 (7)	0.0406 (7)	0.0468 (7)	−0.0039 (5)	−0.0136 (6)	−0.0123 (6)
C7	0.0475 (9)	0.0809 (13)	0.0896 (14)	−0.0185 (9)	−0.0085 (9)	−0.0493 (11)
C8	0.0366 (7)	0.0360 (7)	0.0405 (7)	−0.0016 (5)	−0.0091 (6)	−0.0116 (5)
C9	0.0485 (8)	0.0411 (7)	0.0434 (7)	−0.0006 (6)	−0.0147 (6)	−0.0111 (6)
C10	0.0561 (10)	0.0452 (8)	0.0555 (9)	−0.0002 (7)	−0.0205 (8)	−0.0028 (7)
C11	0.0588 (10)	0.0362 (8)	0.0769 (12)	0.0015 (7)	−0.0197 (9)	−0.0103 (8)
C12	0.0591 (10)	0.0432 (8)	0.0741 (11)	−0.0007 (7)	−0.0146 (9)	−0.0279 (8)
C13	0.0449 (8)	0.0453 (8)	0.0484 (8)	−0.0033 (6)	−0.0105 (6)	−0.0194 (6)
C14	0.0947 (16)	0.0851 (14)	0.0634 (12)	−0.0154 (12)	−0.0221 (11)	−0.0406 (11)
C15	0.0466 (9)	0.0614 (10)	0.0490 (9)	−0.0118 (7)	−0.0026 (7)	−0.0154 (7)
C16	0.0626 (11)	0.0490 (9)	0.0594 (10)	0.0032 (8)	−0.0331 (9)	−0.0098 (7)
C17	0.0393 (7)	0.0368 (6)	0.0383 (7)	−0.0021 (5)	−0.0119 (6)	−0.0139 (5)
C18	0.0432 (8)	0.0455 (7)	0.0399 (7)	−0.0105 (6)	−0.0098 (6)	−0.0111 (6)
C19	0.0613 (10)	0.0489 (8)	0.0395 (7)	−0.0107 (7)	−0.0135 (7)	−0.0059 (6)
C20	0.0576 (10)	0.0576 (9)	0.0464 (8)	−0.0006 (8)	−0.0244 (7)	−0.0109 (7)
C21	0.0462 (8)	0.0541 (9)	0.0503 (8)	−0.0037 (7)	−0.0206 (7)	−0.0154 (7)
C22	0.0411 (7)	0.0388 (7)	0.0406 (7)	−0.0053 (6)	−0.0115 (6)	−0.0134 (5)
C23	0.0613 (11)	0.0673 (12)	0.0800 (13)	−0.0300 (9)	−0.0246 (10)	0.0006 (10)
N1	0.0355 (6)	0.0358 (5)	0.0386 (6)	−0.0020 (4)	−0.0116 (5)	−0.0134 (4)
O1	0.0377 (6)	0.0646 (7)	0.0567 (7)	−0.0090 (5)	−0.0075 (5)	−0.0240 (6)
O2	0.0806 (9)	0.0622 (7)	0.0563 (7)	0.0056 (7)	−0.0293 (7)	−0.0315 (6)
O3	0.0860 (11)	0.0505 (7)	0.0731 (9)	−0.0167 (7)	−0.0029 (8)	0.0063 (6)
O4	0.0521 (7)	0.0488 (6)	0.0535 (6)	−0.0188 (5)	−0.0211 (5)	−0.0029 (5)
Cl1	0.0555 (3)	0.0834 (4)	0.0871 (4)	−0.0249 (2)	−0.0184 (2)	−0.0350 (3)

Geometric parameters (Å, º) top

C1—N1	1.4896 (17)	C12—C13	1.399 (2)
C1—C8	1.5291 (18)	C12—H12	0.9300
C1—C2	1.542 (2)	C13—O2	1.370 (2)
C1—H1	0.9800	C14—O2	1.414 (2)
C2—C3	1.520 (2)	C14—H14A	0.9600
C2—C15	1.525 (2)	C14—H14B	0.9600
C2—H2	0.9800	C14—H14C	0.9600
C3—O3	1.210 (2)	C15—H15A	0.9600
C3—C4	1.510 (2)	C15—H15B	0.9600
C4—C5	1.533 (2)	C15—H15C	0.9600
C4—C16	1.539 (2)	C16—H16A	0.9600
C4—H4	0.9800	C16—H16B	0.9600
C5—N1	1.4866 (17)	C16—H16C	0.9600
C5—C17	1.5308 (18)	C17—C22	1.397 (2)
C5—H5	0.9800	C17—C18	1.400 (2)
C6—O1	1.2238 (18)	C18—C19	1.381 (2)
C6—N1	1.3598 (19)	C18—H18	0.9300
C6—C7	1.521 (2)	C19—C20	1.377 (3)
C7—Cl1	1.755 (2)	C19—H19	0.9300
C7—H7A	0.9700	C20—C21	1.379 (3)
C7—H7B	0.9700	C20—H20	0.9300
C8—C9	1.390 (2)	C21—C22	1.397 (2)
C8—C13	1.396 (2)	C21—H21	0.9300
C9—C10	1.389 (2)	C22—O4	1.3612 (18)
C9—H9	0.9300	C23—O4	1.410 (2)
C10—C11	1.369 (3)	C23—H23A	0.9600
C10—H10	0.9300	C23—H23B	0.9600
C11—C12	1.379 (3)	C23—H23C	0.9600
C11—H11	0.9300

N1—C1—C8	112.28 (11)	O2—C13—C8	116.34 (13)
N1—C1—C2	110.76 (11)	O2—C13—C12	123.70 (15)
C8—C1—C2	109.21 (11)	C8—C13—C12	119.96 (15)
N1—C1—H1	108.2	O2—C14—H14A	109.5
C8—C1—H1	108.2	O2—C14—H14B	109.5
C2—C1—H1	108.2	H14A—C14—H14B	109.5
C3—C2—C15	112.61 (13)	O2—C14—H14C	109.5
C3—C2—C1	110.45 (12)	H14A—C14—H14C	109.5
C15—C2—C1	111.99 (12)	H14B—C14—H14C	109.5
C3—C2—H2	107.2	C2—C15—H15A	109.5
C15—C2—H2	107.2	C2—C15—H15B	109.5
C1—C2—H2	107.2	H15A—C15—H15B	109.5
O3—C3—C4	121.64 (15)	C2—C15—H15C	109.5
O3—C3—C2	122.00 (16)	H15A—C15—H15C	109.5
C4—C3—C2	116.32 (13)	H15B—C15—H15C	109.5
C3—C4—C5	112.21 (11)	C4—C16—H16A	109.5
C3—C4—C16	108.41 (13)	C4—C16—H16B	109.5
C5—C4—C16	110.13 (14)	H16A—C16—H16B	109.5
C3—C4—H4	108.7	C4—C16—H16C	109.5
C5—C4—H4	108.7	H16A—C16—H16C	109.5
C16—C4—H4	108.7	H16B—C16—H16C	109.5
N1—C5—C17	110.48 (10)	C22—C17—C18	117.60 (13)
N1—C5—C4	107.60 (11)	C22—C17—C5	126.74 (13)
C17—C5—C4	121.40 (12)	C18—C17—C5	115.61 (13)
N1—C5—H5	105.4	C19—C18—C17	121.83 (15)
C17—C5—H5	105.4	C19—C18—H18	119.1
C4—C5—H5	105.4	C17—C18—H18	119.1
O1—C6—N1	122.87 (14)	C20—C19—C18	119.29 (15)
O1—C6—C7	121.45 (14)	C20—C19—H19	120.4
N1—C6—C7	115.66 (13)	C18—C19—H19	120.4
C6—C7—Cl1	112.67 (13)	C19—C20—C21	120.68 (15)
C6—C7—H7A	109.1	C19—C20—H20	119.7
Cl1—C7—H7A	109.1	C21—C20—H20	119.7
C6—C7—H7B	109.1	C20—C21—C22	119.85 (16)
Cl1—C7—H7B	109.1	C20—C21—H21	120.1
H7A—C7—H7B	107.8	C22—C21—H21	120.1
C9—C8—C13	118.37 (13)	O4—C22—C21	122.75 (14)
C9—C8—C1	120.37 (12)	O4—C22—C17	116.74 (13)
C13—C8—C1	121.17 (13)	C21—C22—C17	120.49 (14)
C10—C9—C8	121.73 (15)	O4—C23—H23A	109.5
C10—C9—H9	119.1	O4—C23—H23B	109.5
C8—C9—H9	119.1	H23A—C23—H23B	109.5
C11—C10—C9	118.96 (16)	O4—C23—H23C	109.5
C11—C10—H10	120.5	H23A—C23—H23C	109.5
C9—C10—H10	120.5	H23B—C23—H23C	109.5
C10—C11—C12	121.17 (15)	C6—N1—C5	117.12 (11)
C10—C11—H11	119.4	C6—N1—C1	122.55 (11)
C12—C11—H11	119.4	C5—N1—C1	119.22 (11)
C11—C12—C13	119.81 (16)	C13—O2—C14	118.37 (15)
C11—C12—H12	120.1	C22—O4—C23	119.13 (13)
C13—C12—H12	120.1

N1—C1—C2—C3	−47.55 (15)	C11—C12—C13—C8	−0.6 (3)
C8—C1—C2—C3	−171.71 (12)	N1—C5—C17—C22	116.22 (15)
N1—C1—C2—C15	−173.93 (12)	C4—C5—C17—C22	−11.1 (2)
C8—C1—C2—C15	61.92 (15)	N1—C5—C17—C18	−61.14 (16)
C15—C2—C3—O3	−4.8 (2)	C4—C5—C17—C18	171.55 (12)
C1—C2—C3—O3	−130.78 (19)	C22—C17—C18—C19	−3.6 (2)
C15—C2—C3—C4	172.96 (14)	C5—C17—C18—C19	173.98 (13)
C1—C2—C3—C4	46.93 (18)	C17—C18—C19—C20	−0.8 (2)
O3—C3—C4—C5	−177.97 (18)	C18—C19—C20—C21	3.7 (3)
C2—C3—C4—C5	4.31 (19)	C19—C20—C21—C22	−2.0 (2)
O3—C3—C4—C16	60.2 (2)	C20—C21—C22—O4	178.85 (14)
C2—C3—C4—C16	−117.54 (16)	C20—C21—C22—C17	−2.6 (2)
C3—C4—C5—N1	−52.29 (16)	C18—C17—C22—O4	−176.08 (12)
C16—C4—C5—N1	68.57 (14)	C5—C17—C22—O4	6.6 (2)
C3—C4—C5—C17	76.29 (16)	C18—C17—C22—C21	5.3 (2)
C16—C4—C5—C17	−162.84 (12)	C5—C17—C22—C21	−171.99 (13)
O1—C6—C7—Cl1	0.0 (2)	O1—C6—N1—C5	−12.0 (2)
N1—C6—C7—Cl1	−178.78 (13)	C7—C6—N1—C5	166.80 (14)
N1—C1—C8—C9	−54.71 (18)	O1—C6—N1—C1	−179.81 (13)
C2—C1—C8—C9	68.55 (17)	C7—C6—N1—C1	−1.0 (2)
N1—C1—C8—C13	128.78 (15)	C17—C5—N1—C6	109.92 (14)
C2—C1—C8—C13	−107.96 (16)	C4—C5—N1—C6	−115.50 (13)
C13—C8—C9—C10	−0.1 (2)	C17—C5—N1—C1	−81.81 (14)
C1—C8—C9—C10	−176.73 (15)	C4—C5—N1—C1	52.77 (15)
C8—C9—C10—C11	0.0 (3)	C8—C1—N1—C6	−72.11 (16)
C9—C10—C11—C12	−0.2 (3)	C2—C1—N1—C6	165.51 (12)
C10—C11—C12—C13	0.5 (3)	C8—C1—N1—C5	120.29 (13)
C9—C8—C13—O2	179.59 (15)	C2—C1—N1—C5	−2.09 (15)
C1—C8—C13—O2	−3.8 (2)	C8—C13—O2—C14	177.07 (18)
C9—C8—C13—C12	0.4 (2)	C12—C13—O2—C14	−3.7 (3)
C1—C8—C13—C12	176.96 (15)	C21—C22—O4—C23	−1.4 (2)
C11—C12—C13—O2	−179.72 (18)	C17—C22—O4—C23	−179.98 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23C···O1ⁱ	0.96	2.50	3.321 (3)	144
C9—H9···Cg	0.93	2.69	3.621 (2)	177

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₆ClNO₄
M_r	415.90
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.9921 (6), 11.3725 (8), 11.9373 (8)
α, β, γ (°)	71.630 (1), 68.465 (1), 72.903 (1)
V (Å³)	1055.45 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.27 × 0.22 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11114, 4603, 4054
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.145, 1.05
No. of reflections	4603
No. of parameters	266
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.35

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and PARST (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23C···O1ⁱ	0.96	2.50	3.321 (3)	144
C9—H9···Cg	0.93	2.69	3.621 (2)	177

Symmetry code: (i) x+1, y, z.

Footnotes

‡Present address: Institute of Structural Biology and Biophysics-2, Forschungszentrum Jülich, D-52425 Jülich, Germany.

Acknowledgements

The authors thank Dr K. Ravikumar, Indian Institute of Chemical Technology, Hyderabad, India, for providing the X-ray data collection facility. GA and YTJ acknowledge the support provided by the second stage of the BK21 program, Republic of Korea. Financial support from the University Grants Commission (UGC–SAP) and the Department of Science & Technology (DST-FIST), Government of India, are acknowledged by DV for providing facilities to the department.

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