Crystal structure of 2,6-bis­(2,5-di­meth­oxy­phen­yl)-3,5-di­methyl­piperidin-4-one

Park, D.H.; Ramkumar, V.; Parthiban, P.

doi:10.1107/S1600536814022041

organic compounds

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Volume 70| Part 11| November 2014| Page o1160

doi:10.1107/S1600536814022041

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Crystal structure of 2,6-bis(2,5-dimethoxyphenyl)-3,5-dimethylpiperidin-4-one

Dong Ho Park,^a V. Ramkumar ^b and P. Parthiban ^a,^c ^*

^aDepartment of Biomedicinal Chemistry, Inje University, Gimhae, Gyeongnam 621 749, Republic of Korea, ^bDepartment of Chemistry, IIT Madras, Chennai 600 036, TamilNadu, India, and ^cDepartment of Chemistry, VEL TECH, Avadi, Chennai 600 062, India
^*Correspondence e-mail: parthisivam@yahoo.co.in

Edited by V. V. Chernyshev, Moscow State University, Russia (Received 24 July 2014; accepted 7 October 2014; online 15 October 2014)

In the title molecule, C₂₃H₂₉NO₅, the central piperidine ring has a chair conformation. The planes of the two benzene rings are inclined each to other at 61.7 (1)°. The crystal packing exhibits no directional interactions only van der Waals contacts.

Keywords: crystal structure; chair conformation; Mannich base; piperidin-4-one.

CCDC reference: 1027842

1. Related literature

For the synthesis, stereochemistry and biological actions of piperidin-4-ones, see: Sahu et al. (2013 ); Parthiban et al. (2011 ). For a related crystal structure, see: Parthiban et al. (2008 ).

2. Experimental

2.1. Crystal data

C₂₃H₂₉NO₅
M_r = 399.47
Monoclinic, P 2₁ /c
a = 11.1358 (7) Å
b = 9.4756 (5) Å
c = 20.4541 (11) Å
β = 92.271 (2)°
V = 2156.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.25 × 0.20 × 0.15 mm

2.2. Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.979, T_max = 0.987
11151 measured reflections
3536 independent reflections
2262 reflections with I > 2σ(I)
R_int = 0.029

2.3. Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.116
S = 0.98
3536 reflections
272 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

CCDC reference: 1027842

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814022041/cv5470sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814022041/cv5470Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814022041/cv5470Isup3.cml

checkCIF report

Comment top

The piperidin-4-one pharmacophore is responsible for numerous biological actions such as antibacterial, antimycobacterial, antifungal, anticancer, antioxidant, antiinflammatory, neuronal nicotinistinic, and CNS stimulant and depressant. Its activity is further increased by the incorporation of aryl groups on both sides of the hetero atom along with/without the introduction of functionalities on the hetero atom itself. Interestingly, the amino group of the piperidone that is flanked by aryl groups are responsible not only for the increment in activity, but also in suppressing the toxicity (Sahu et al. 2013; Parthiban et al. 2011). Generally, the piperidin-4-one moiety exists in different stereochemistries upon the modifications in their structure. Since the stereochemistry of the molecule is an important key for its biological response, it is of curious to explore the stereochemistry. Hence the present study is caried out to explore the stereochemistry of the title compound (I) (Fig. 1).

The crystallographic parameters viz., torsion angles, asymmetry parameters and ring puckering parameters calculated for (I) show that the piperidone ring adopts a chair conformation. According to Cremer & Pople and Nardelli, the total puckering amplitude, Q_T is 0.5875 (8) Å, the phase angle θ is 0.94 (8)° and phi is 34 (4)°. The smallest displacement asymmetry parameters q₂ and q₃ are 0.0114 (8) and -0.5874 Å, respectively.

The benzene rings of anisyl groups are oriented at an angle of 61.7 (1)°, respect to each other. The torsion angles of C6—C1—C2—C3 and C3—C4—C5—C16 are 174.94 (18) and -174.42 (18)°, respectively. Similarly, the torsion angles of C2—C3—C4—C15 and C14—C2—C3—C4 are -177.8 (2) and 177.1 (2)%, respectively. The torsion angle values also clearly confirm the equatorial orientation of aryl and alkyl groups on the piperidin-4-one moiety.

On the whole, the complete crystallographic analysis of the title compound, C₂₃H₂₉NO₅, exhibits a chair conformation with equatorial orientations of all the aryl and alkyl substituents.

Related literature top

For the synthesis, stereochemistry and biological actions of piperidin-4-ones, see: Sahu et al. (2013); Parthiban et al. (2011). For a related crystal structure, see: Parthiban et al. (2008).

Experimental top

The 2,6-bis(2,5-dimethoxyphenyl)-3,5-dimethylpiperidin-4-one was synthesized by a modified and an optimized Mannich condensation in one-pot, using 2,5-dimethoxybenzaldehyde (0.1 mol, 16.618 g), 2-pentanone (0.05 mol) and ammonium acetate (0.075 mol, 5.78 g) in a 50 ml of absolute ethanol (Parthiban et al., 2011). The mixture was gently warmed on a hot plate at 303–308 K (30–35° C) with moderate stirring till the complete consumption of the starting materials, which was monitored by TLC. At the end, the crude azabicyclic ketone was separated by filtration and gently washed with 1:5 cold ethanol-ether mixture. X-ray diffraction quality crystals of the title compound were obtained by slow evaporation from ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Figure 1. View of (I) showing the atomic numbering and 30% probability displacement ellipsoids.

2,6-Bis(2,5-dimethoxyphenyl)-3,5-dimethylpiperidin-4-one top

Crystal data top

C₂₃H₂₉NO₅	Z = 4
M_r = 399.47	F(000) = 856
Monoclinic, P2₁/c	D_x = 1.230 Mg m⁻³
a = 11.1358 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.4756 (5) Å	µ = 0.09 mm⁻¹
c = 20.4541 (11) Å	T = 298 K
β = 92.271 (2)°	Block, yellow
V = 2156.6 (2) Å³	0.25 × 0.20 × 0.15 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	2262 reflections with I > 2σ(I)
phi and ω scans	R_int = 0.029
Absorption correction: multi-scan (SADABS; Bruker, 2004)	θ_max = 25.0°, θ_min = 2.4°
T_min = 0.979, T_max = 0.987	h = −12→12
11151 measured reflections	k = −11→10
3536 independent reflections	l = −20→24

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.116	w = 1/[σ²(F_o²) + (0.0405P)² + 0.9547P] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max < 0.001
3536 reflections	Δρ_max = 0.17 e Å⁻³
272 parameters	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₃H₂₉NO₅	V = 2156.6 (2) Å³
M_r = 399.47	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.1358 (7) Å	µ = 0.09 mm⁻¹
b = 9.4756 (5) Å	T = 298 K
c = 20.4541 (11) Å	0.25 × 0.20 × 0.15 mm
β = 92.271 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3536 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2262 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.987	R_int = 0.029
11151 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	Δρ_max = 0.17 e Å⁻³
3536 reflections	Δρ_min = −0.18 e Å⁻³
272 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.54320 (17)	0.4952 (2)	0.14728 (9)	0.0380 (5)
H1	0.5445	0.3918	0.1468	0.046*
C2	0.59048 (18)	0.5485 (2)	0.21515 (10)	0.0439 (5)
H2	0.5876	0.6519	0.2147	0.053*
C3	0.50346 (19)	0.4971 (2)	0.26472 (10)	0.0447 (6)
C4	0.37508 (18)	0.5434 (3)	0.25295 (10)	0.0465 (6)
H4	0.3737	0.6469	0.2526	0.056*
C5	0.33417 (17)	0.4916 (2)	0.18398 (9)	0.0413 (5)
H5	0.3343	0.3882	0.1834	0.050*
C6	0.61644 (17)	0.5504 (2)	0.09201 (9)	0.0369 (5)
C7	0.6022 (2)	0.6895 (2)	0.07205 (10)	0.0461 (6)
H7	0.5514	0.7484	0.0946	0.055*
C8	0.6620 (2)	0.7426 (2)	0.01924 (11)	0.0510 (6)
C9	0.7397 (2)	0.6581 (3)	−0.01319 (10)	0.0520 (6)
H9	0.7807	0.6936	−0.0484	0.062*
C10	0.7570 (2)	0.5200 (3)	0.00665 (10)	0.0495 (6)
H10	0.8106	0.4631	−0.0150	0.059*
C11	0.69529 (18)	0.4653 (2)	0.05833 (9)	0.0404 (5)
C12	0.6457 (4)	0.9225 (3)	−0.06178 (14)	0.1112 (13)
H12A	0.7285	0.9324	−0.0725	0.167*
H12B	0.6053	1.0112	−0.0681	0.167*
H12C	0.6080	0.8525	−0.0896	0.167*
C13	0.7419 (4)	0.2273 (3)	0.03408 (15)	0.1146 (14)
H13A	0.6913	0.2362	−0.0048	0.172*
H13B	0.7329	0.1347	0.0523	0.172*
H13C	0.8242	0.2416	0.0233	0.172*
C14	0.7187 (2)	0.5047 (3)	0.23158 (12)	0.0684 (8)
H14A	0.7390	0.5282	0.2763	0.103*
H14B	0.7718	0.5533	0.2034	0.103*
H14C	0.7266	0.4047	0.2255	0.103*
C15	0.2921 (2)	0.4933 (3)	0.30574 (12)	0.0722 (8)
H15A	0.2847	0.3924	0.3037	0.108*
H15B	0.2143	0.5355	0.2988	0.108*
H15C	0.3251	0.5203	0.3480	0.108*
C16	0.20999 (18)	0.5443 (2)	0.16386 (10)	0.0425 (5)
C17	0.10969 (19)	0.4552 (3)	0.16077 (11)	0.0487 (6)
C18	0.0001 (2)	0.5069 (3)	0.13831 (12)	0.0595 (7)
H18	−0.0658	0.4466	0.1353	0.071*
C19	−0.0138 (2)	0.6459 (3)	0.12020 (12)	0.0610 (7)
H19	−0.0886	0.6794	0.1055	0.073*
C20	0.0835 (2)	0.7349 (3)	0.12398 (11)	0.0534 (6)
C21	0.1949 (2)	0.6839 (3)	0.14593 (10)	0.0480 (6)
H21	0.2604	0.7448	0.1486	0.058*
C22	0.0276 (3)	0.2382 (4)	0.19599 (19)	0.1093 (13)
H22A	−0.0150	0.2881	0.2287	0.164*
H22B	0.0536	0.1484	0.2131	0.164*
H22C	−0.0244	0.2240	0.1580	0.164*
C23	−0.0296 (3)	0.9292 (4)	0.08139 (18)	0.1084 (12)
H23A	−0.0539	0.8772	0.0428	0.163*
H23B	−0.0200	1.0270	0.0704	0.163*
H23C	−0.0897	0.9201	0.1135	0.163*
N1	0.41929 (15)	0.5441 (2)	0.13674 (9)	0.0418 (5)
O1	0.6391 (2)	0.88138 (18)	0.00307 (9)	0.0849 (6)
O2	0.70918 (15)	0.32842 (17)	0.07975 (7)	0.0610 (5)
O3	0.53408 (14)	0.4179 (2)	0.30899 (8)	0.0667 (5)
O4	0.12791 (14)	0.31712 (18)	0.17881 (9)	0.0684 (5)
O5	0.08013 (16)	0.8756 (2)	0.10695 (10)	0.0790 (6)
H1N	0.3918 (19)	0.522 (2)	0.0956 (11)	0.054 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0316 (12)	0.0430 (13)	0.0398 (12)	−0.0014 (10)	0.0056 (9)	−0.0003 (9)
C2	0.0343 (13)	0.0565 (14)	0.0410 (12)	−0.0045 (11)	0.0012 (9)	0.0011 (10)
C3	0.0425 (14)	0.0560 (15)	0.0355 (12)	−0.0051 (11)	0.0007 (10)	−0.0054 (11)
C4	0.0396 (14)	0.0601 (15)	0.0405 (12)	0.0024 (11)	0.0086 (10)	−0.0017 (11)
C5	0.0325 (13)	0.0491 (14)	0.0428 (12)	−0.0005 (10)	0.0065 (9)	−0.0020 (10)
C6	0.0293 (12)	0.0436 (13)	0.0378 (11)	−0.0002 (10)	0.0020 (9)	−0.0019 (9)
C7	0.0478 (14)	0.0469 (15)	0.0442 (13)	0.0044 (11)	0.0081 (10)	−0.0026 (10)
C8	0.0621 (16)	0.0460 (15)	0.0452 (13)	−0.0051 (13)	0.0062 (12)	0.0016 (11)
C9	0.0586 (16)	0.0618 (17)	0.0364 (12)	−0.0123 (13)	0.0106 (11)	0.0012 (11)
C10	0.0435 (14)	0.0636 (17)	0.0422 (13)	0.0039 (12)	0.0122 (10)	−0.0060 (11)
C11	0.0377 (13)	0.0461 (14)	0.0374 (11)	0.0030 (11)	0.0028 (10)	−0.0005 (10)
C12	0.191 (4)	0.077 (2)	0.065 (2)	0.003 (2)	0.001 (2)	0.0232 (16)
C13	0.212 (4)	0.059 (2)	0.075 (2)	0.041 (2)	0.034 (2)	−0.0018 (16)
C14	0.0398 (15)	0.111 (2)	0.0547 (15)	−0.0071 (15)	−0.0020 (11)	0.0093 (15)
C15	0.0505 (16)	0.117 (2)	0.0500 (15)	0.0073 (16)	0.0181 (12)	0.0062 (15)
C16	0.0325 (13)	0.0549 (15)	0.0407 (12)	0.0019 (11)	0.0079 (9)	−0.0023 (10)
C17	0.0326 (14)	0.0611 (17)	0.0530 (14)	0.0022 (12)	0.0087 (10)	−0.0008 (12)
C18	0.0338 (15)	0.0736 (19)	0.0712 (17)	−0.0039 (13)	0.0049 (12)	0.0005 (14)
C19	0.0351 (15)	0.083 (2)	0.0648 (17)	0.0121 (15)	0.0022 (12)	0.0024 (14)
C20	0.0474 (16)	0.0579 (17)	0.0556 (15)	0.0122 (14)	0.0087 (12)	0.0018 (12)
C21	0.0368 (14)	0.0584 (16)	0.0494 (13)	0.0013 (12)	0.0085 (10)	−0.0027 (11)
C22	0.065 (2)	0.098 (3)	0.165 (3)	−0.0243 (19)	0.002 (2)	0.051 (2)
C23	0.096 (3)	0.102 (3)	0.128 (3)	0.043 (2)	0.012 (2)	0.030 (2)
N1	0.0293 (10)	0.0615 (13)	0.0347 (10)	0.0010 (9)	0.0031 (8)	−0.0022 (9)
O1	0.1432 (19)	0.0502 (12)	0.0627 (12)	0.0013 (11)	0.0232 (11)	0.0144 (9)
O2	0.0819 (12)	0.0503 (10)	0.0522 (10)	0.0217 (9)	0.0209 (8)	0.0043 (8)
O3	0.0544 (11)	0.0958 (14)	0.0499 (10)	0.0008 (10)	0.0020 (8)	0.0231 (9)
O4	0.0420 (10)	0.0605 (12)	0.1031 (14)	−0.0078 (9)	0.0086 (9)	0.0132 (10)
O5	0.0660 (13)	0.0680 (13)	0.1032 (15)	0.0206 (10)	0.0044 (10)	0.0128 (11)

Geometric parameters (Å, º) top

C1—N1	1.463 (2)	C13—O2	1.396 (3)
C1—C6	1.513 (3)	C13—H13A	0.9600
C1—C2	1.550 (3)	C13—H13B	0.9600
C1—H1	0.9800	C13—H13C	0.9600
C2—C14	1.511 (3)	C14—H14A	0.9600
C2—C3	1.511 (3)	C14—H14B	0.9600
C2—H2	0.9800	C14—H14C	0.9600
C3—O3	1.215 (2)	C15—H15A	0.9600
C3—C4	1.506 (3)	C15—H15B	0.9600
C4—C15	1.525 (3)	C15—H15C	0.9600
C4—C5	1.545 (3)	C16—C21	1.381 (3)
C4—H4	0.9800	C16—C17	1.399 (3)
C5—N1	1.467 (2)	C17—O4	1.373 (3)
C5—C16	1.512 (3)	C17—C18	1.377 (3)
C5—H5	0.9800	C18—C19	1.376 (3)
C6—C7	1.388 (3)	C18—H18	0.9300
C6—C11	1.394 (3)	C19—C20	1.372 (3)
C7—C8	1.386 (3)	C19—H19	0.9300
C7—H7	0.9300	C20—O5	1.378 (3)
C8—C9	1.369 (3)	C20—C21	1.389 (3)
C8—O1	1.378 (3)	C21—H21	0.9300
C9—C10	1.381 (3)	C22—O4	1.400 (3)
C9—H9	0.9300	C22—H22A	0.9600
C10—C11	1.384 (3)	C22—H22B	0.9600
C10—H10	0.9300	C22—H22C	0.9600
C11—O2	1.376 (2)	C23—O5	1.405 (3)
C12—O1	1.387 (3)	C23—H23A	0.9600
C12—H12A	0.9600	C23—H23B	0.9600
C12—H12B	0.9600	C23—H23C	0.9600
C12—H12C	0.9600	N1—H1N	0.91 (2)

N1—C1—C6	108.28 (16)	H13A—C13—H13B	109.5
N1—C1—C2	108.30 (16)	O2—C13—H13C	109.5
C6—C1—C2	112.50 (16)	H13A—C13—H13C	109.5
N1—C1—H1	109.2	H13B—C13—H13C	109.5
C6—C1—H1	109.2	C2—C14—H14A	109.5
C2—C1—H1	109.2	C2—C14—H14B	109.5
C14—C2—C3	112.79 (18)	H14A—C14—H14B	109.5
C14—C2—C1	113.20 (18)	C2—C14—H14C	109.5
C3—C2—C1	106.98 (16)	H14A—C14—H14C	109.5
C14—C2—H2	107.9	H14B—C14—H14C	109.5
C3—C2—H2	107.9	C4—C15—H15A	109.5
C1—C2—H2	107.9	C4—C15—H15B	109.5
O3—C3—C4	122.4 (2)	H15A—C15—H15B	109.5
O3—C3—C2	122.1 (2)	C4—C15—H15C	109.5
C4—C3—C2	115.40 (18)	H15A—C15—H15C	109.5
C3—C4—C15	113.20 (19)	H15B—C15—H15C	109.5
C3—C4—C5	107.28 (16)	C21—C16—C17	118.5 (2)
C15—C4—C5	112.49 (19)	C21—C16—C5	119.26 (19)
C3—C4—H4	107.9	C17—C16—C5	122.2 (2)
C15—C4—H4	107.9	O4—C17—C18	123.2 (2)
C5—C4—H4	107.9	O4—C17—C16	117.0 (2)
N1—C5—C16	108.48 (17)	C18—C17—C16	119.8 (2)
N1—C5—C4	108.59 (17)	C17—C18—C19	121.3 (2)
C16—C5—C4	112.15 (17)	C17—C18—H18	119.4
N1—C5—H5	109.2	C19—C18—H18	119.4
C16—C5—H5	109.2	C20—C19—C18	119.5 (2)
C4—C5—H5	109.2	C20—C19—H19	120.2
C7—C6—C11	118.11 (19)	C18—C19—H19	120.2
C7—C6—C1	119.29 (18)	C19—C20—O5	124.5 (2)
C11—C6—C1	122.56 (19)	C19—C20—C21	119.8 (2)
C8—C7—C6	121.4 (2)	O5—C20—C21	115.7 (2)
C8—C7—H7	119.3	C16—C21—C20	121.1 (2)
C6—C7—H7	119.3	C16—C21—H21	119.4
C9—C8—O1	123.8 (2)	C20—C21—H21	119.4
C9—C8—C7	119.9 (2)	O4—C22—H22A	109.5
O1—C8—C7	116.3 (2)	O4—C22—H22B	109.5
C8—C9—C10	119.6 (2)	H22A—C22—H22B	109.5
C8—C9—H9	120.2	O4—C22—H22C	109.5
C10—C9—H9	120.2	H22A—C22—H22C	109.5
C11—C10—C9	120.8 (2)	H22B—C22—H22C	109.5
C11—C10—H10	119.6	O5—C23—H23A	109.5
C9—C10—H10	119.6	O5—C23—H23B	109.5
O2—C11—C10	122.92 (19)	H23A—C23—H23B	109.5
O2—C11—C6	116.93 (18)	O5—C23—H23C	109.5
C10—C11—C6	120.1 (2)	H23A—C23—H23C	109.5
O1—C12—H12A	109.5	H23B—C23—H23C	109.5
O1—C12—H12B	109.5	C1—N1—C5	115.22 (16)
H12A—C12—H12B	109.5	C1—N1—H1N	110.3 (13)
O1—C12—H12C	109.5	C5—N1—H1N	109.3 (13)
H12A—C12—H12C	109.5	C8—O1—C12	118.8 (2)
H12B—C12—H12C	109.5	C11—O2—C13	117.55 (19)
O2—C13—H13A	109.5	C17—O4—C22	117.8 (2)
O2—C13—H13B	109.5	C20—O5—C23	117.3 (2)

N1—C1—C2—C14	−179.85 (19)	C7—C6—C11—C10	0.1 (3)
C6—C1—C2—C14	−60.2 (2)	C1—C6—C11—C10	177.74 (19)
N1—C1—C2—C3	55.3 (2)	N1—C5—C16—C21	−45.6 (3)
C6—C1—C2—C3	174.94 (18)	C4—C5—C16—C21	74.4 (2)
C14—C2—C3—O3	−6.6 (3)	N1—C5—C16—C17	132.4 (2)
C1—C2—C3—O3	118.5 (2)	C4—C5—C16—C17	−107.7 (2)
C14—C2—C3—C4	177.1 (2)	C21—C16—C17—O4	179.87 (19)
C1—C2—C3—C4	−57.8 (2)	C5—C16—C17—O4	1.9 (3)
O3—C3—C4—C15	5.9 (3)	C21—C16—C17—C18	1.9 (3)
C2—C3—C4—C15	−177.8 (2)	C5—C16—C17—C18	−176.0 (2)
O3—C3—C4—C5	−118.8 (2)	O4—C17—C18—C19	−179.4 (2)
C2—C3—C4—C5	57.5 (2)	C16—C17—C18—C19	−1.6 (4)
C3—C4—C5—N1	−54.6 (2)	C17—C18—C19—C20	0.6 (4)
C15—C4—C5—N1	−179.68 (19)	C18—C19—C20—O5	179.7 (2)
C3—C4—C5—C16	−174.42 (18)	C18—C19—C20—C21	0.1 (4)
C15—C4—C5—C16	60.5 (3)	C17—C16—C21—C20	−1.3 (3)
N1—C1—C6—C7	44.2 (2)	C5—C16—C21—C20	176.73 (19)
C2—C1—C6—C7	−75.5 (2)	C19—C20—C21—C16	0.3 (3)
N1—C1—C6—C11	−133.4 (2)	O5—C20—C21—C16	−179.4 (2)
C2—C1—C6—C11	106.9 (2)	C6—C1—N1—C5	176.09 (17)
C11—C6—C7—C8	1.5 (3)	C2—C1—N1—C5	−61.6 (2)
C1—C6—C7—C8	−176.22 (19)	C16—C5—N1—C1	−176.60 (17)
C6—C7—C8—C9	−1.9 (3)	C4—C5—N1—C1	61.3 (2)
C6—C7—C8—O1	178.8 (2)	C9—C8—O1—C12	30.9 (4)
O1—C8—C9—C10	179.9 (2)	C7—C8—O1—C12	−149.8 (3)
C7—C8—C9—C10	0.7 (3)	C10—C11—O2—C13	−28.2 (3)
C8—C9—C10—C11	0.9 (3)	C6—C11—O2—C13	153.0 (3)
C9—C10—C11—O2	179.8 (2)	C18—C17—O4—C22	−21.9 (4)
C9—C10—C11—C6	−1.3 (3)	C16—C17—O4—C22	160.3 (2)
C7—C6—C11—O2	179.04 (18)	C19—C20—O5—C23	−2.8 (4)
C1—C6—C11—O2	−3.3 (3)	C21—C20—O5—C23	176.8 (2)

Experimental details

Crystal data
Chemical formula	C₂₃H₂₉NO₅
M_r	399.47
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	11.1358 (7), 9.4756 (5), 20.4541 (11)
β (°)	92.271 (2)
V (Å³)	2156.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.979, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	11151, 3536, 2262
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.116, 0.98
No. of reflections	3536
No. of parameters	272
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.18

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), SHELXTL (Sheldrick, 2008).

Acknowledgements

This research was supported by Inje University Research Grant 2013. The authors acknowledge the Department of Chemistry, IIT Madras, for the X-ray data collection.

References

Bruker (2004). APEXII, XPREP, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
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