1-Formyl-r-2,c-6-bis­(4-methoxy­phen­yl)-t-3,t-5-dimethyl­piperidin-4-one

Kavitha, T.; Sakthivel, P.; Ponnuswamy, S.; Ilango, S.S.; Ponnuswamy, M.N.

doi:10.1107/S1600536809041609

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2818

https://doi.org/10.1107/S1600536809041609

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1-Formyl-r-2,c-6-bis(4-methoxyphenyl)-t-3,t-5-dimethylpiperidin-4-one

T. Kavitha,^a P. Sakthivel,^b S. Ponnuswamy,^b S. S. Ilango ^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, Tamil Nadu, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 12 September 2009; accepted 12 October 2009; online 23 October 2009)

In the title compound, C₂₂H₂₅NO₄, the piperidine ring adopts a distorted boat conformation. The methyl groups at the 3 and 5 positions of the piperidine ring are in axial and equatorial orientations, respectively. Both H and O atoms in the aldehyde group are disordered over two positions with occupancies of 0.534 (5) and 0.466 (5). In the crystal, the molecules are linked into a three-dimensional network by C—H⋯O hydrogen bonds.

Related literature

For general background to piperidine derivatives, see: Escolano & Amat (2006 ); Wang & Wuorola (1992 ); Grishina et al. (1994 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₂H₂₅NO₄
M_r = 367.43
Monoclinic, P 2₁ /n
a = 11.0954 (4) Å
b = 14.5407 (3) Å
c = 12.7050 (4) Å
β = 110.977 (1)°
V = 1913.91 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.974, T_max = 0.974
24720 measured reflections
5524 independent reflections
3703 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.140
S = 1.05
5524 reflections
256 parameters
H-atom parameters constrained
Δρ_max = 0.23 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
C3—H3⋯O1ⁱ	0.98	2.48	3.429 (2)	163
C15—H15C⋯O2ⁱⁱ	0.96	2.53	3.240 (4)	131
C20—H20⋯O1ⁱⁱⁱ	0.93	2.51	3.432 (2)	171
Symmetry codes: (i) -x+2, -y, -z; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); 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 I, global. DOI: https://doi.org/10.1107/S1600536809041609/ci2909sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809041609/ci2909Isup2.hkl

checkCIF report

Comment top

The piperidine ring is a common feature occurring in many biologically active natural products and therapeutic agents. Piperidine containing entities constitute important targets for pharmaceutical research (Escolano & Amat, 2006). Piperidine derivatives, namely 4-piperidones are synthetic intermediates in the preparation of various alkaloids and pharmaceutical products (Wang et al., 1992; Grishina et al., 1994).

In the title molecule (Fig.1), the piperidine ring adopts a distorted boat conformation. The methyl groups at 3 and 5 positions of the piperidine ring are in axial and equatorial orientations [N1—C2—C3—C14 = -63.02 (15)° and N1—C6—C5—C15 = 176.60 (11)°]. The phenyl rings at 2 and 6 positions of the piperidine ring are axially [C4—C3—C2—C8 = -68.32 (14)°] and equatorially [C4—C5—C6—C16 = 176.69 (10)°] oriented. The dihedral angle between the two phenyl rings is 41.97 (8)°.

Centrosymmetrically related molecules form R₂²(8) (Bernstein et al., 1995) dimers through C—H···O hydrogen bonds involving atoms C3 and O1. The dimers are linked into a zigzag C(8) chain running along the b axis by intermolecular C—H···O hydrogen bonds involving atoms C20 and O1 (Table 1). Further, C15—H15C···O2 interactions link the chains along the c axis to form a three-dimensional network.

Related literature top

For general background to piperidine derivatives, see: Escolano & Amat (2006); Wang et al. (1992); Grishina et al. (1994). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

An ice-cold solution of acetic-formic anhydride was prepared from acetic anhydride (10 ml) and 85% formic acid (5 ml) and was added slowly to a cold solution of r-2,c-6-bis(4-methoxyphenyl)-t-3,t-5-dimethylpiperidin-4-one (1.69 g) in benzene (30 ml). The reaction mixture was stirred at room temperature for 5 h. The organic layer was separated, dried over anhydrous Na₂SO₄ and concentrated. The resulting mass was purified by crystallization from benzene-petroleum ether (333–353 K) in the ratio 1:1.

Structure description top

For general background to piperidine derivatives, see: Escolano & Amat (2006); Wang et al. (1992); Grishina et al. (1994). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. Both disorder components are shown. H atoms have been omitted for clarity.
	Fig. 2. The crystal packing of the title compound. H atoms not involved in hydrogen bonding (dashed lines) have been omitted.

1-Formyl-r-2,c-6-bis(4-methoxyphenyl)- t-3,t-5-dimethylpiperidin-4-one top

Crystal data top

C₂₂H₂₅NO₄	F(000) = 784
M_r = 367.43	D_x = 1.275 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5524 reflections
a = 11.0954 (4) Å	θ = 2.1–29.9°
b = 14.5407 (3) Å	µ = 0.09 mm⁻¹
c = 12.7050 (4) Å	T = 293 K
β = 110.977 (1)°	Block, colourless
V = 1913.91 (10) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	5524 independent reflections
Radiation source: fine-focus sealed tube	3703 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω and φ scans	θ_max = 29.9°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −15→12
T_min = 0.974, T_max = 0.974	k = −20→19
24720 measured reflections	l = −17→17

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0598P)² + 0.3189P] where P = (F_o² + 2F_c²)/3
5524 reflections	(Δ/σ)_max = 0.001
256 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₂H₂₅NO₄	V = 1913.91 (10) Å³
M_r = 367.43	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.0954 (4) Å	µ = 0.09 mm⁻¹
b = 14.5407 (3) Å	T = 293 K
c = 12.7050 (4) Å	0.30 × 0.20 × 0.20 mm
β = 110.977 (1)°

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	5524 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	3703 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.974	R_int = 0.029
24720 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.05	Δρ_max = 0.23 e Å⁻³
5524 reflections	Δρ_min = −0.23 e Å⁻³
256 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	Occ. (<1)
O1	0.87856 (11)	0.03534 (7)	0.05971 (10)	0.0574 (3)
O2	1.0929 (3)	0.3733 (2)	0.3086 (2)	0.1143 (15)	0.534 (5)
O2'	1.2050 (3)	0.3881 (2)	0.2198 (3)	0.1036 (16)	0.466 (5)
O3	0.92438 (12)	0.33025 (8)	−0.37580 (9)	0.0647 (3)
O4	0.60958 (11)	0.58982 (7)	0.13202 (9)	0.0600 (3)
N1	1.03399 (11)	0.28962 (8)	0.15129 (9)	0.0446 (3)
C2	1.08936 (13)	0.22990 (9)	0.08641 (11)	0.0433 (3)
H2	1.1831	0.2389	0.1177	0.052*
C3	1.06451 (13)	0.13017 (10)	0.10905 (12)	0.0455 (3)
H3	1.0976	0.0906	0.0631	0.055*
C4	0.92172 (13)	0.11238 (9)	0.07622 (11)	0.0408 (3)
C5	0.83662 (12)	0.19522 (9)	0.06811 (11)	0.0397 (3)
H5	0.8182	0.2227	−0.0064	0.048*
C6	0.90568 (13)	0.26797 (9)	0.15605 (10)	0.0402 (3)
H6	0.9198	0.2415	0.2305	0.048*
C7	1.1102 (2)	0.34871 (18)	0.22651 (19)	0.0930 (7)
H7	1.1815	0.3720	0.2133	0.112*	0.534 (5)
H7'	1.0887	0.3619	0.2918	0.112*	0.466 (5)
C8	1.04508 (12)	0.25691 (9)	−0.03708 (11)	0.0405 (3)
C9	1.01446 (16)	0.19282 (10)	−0.12353 (13)	0.0536 (4)
H9	1.0200	0.1305	−0.1062	0.064*
C10	0.97608 (17)	0.21971 (11)	−0.23422 (13)	0.0582 (4)
H10	0.9554	0.1753	−0.2906	0.070*
C11	0.96764 (14)	0.31160 (10)	−0.26313 (12)	0.0472 (3)
C12	1.00016 (15)	0.37652 (10)	−0.17907 (13)	0.0517 (4)
H12	0.9968	0.4387	−0.1968	0.062*
C13	1.03795 (14)	0.34869 (10)	−0.06774 (13)	0.0496 (3)
H13	1.0593	0.3932	−0.0115	0.060*
C14	1.13194 (17)	0.10344 (14)	0.23312 (14)	0.0675 (5)
H14A	1.2219	0.1187	0.2568	0.101*
H14B	1.1227	0.0385	0.2417	0.101*
H14C	1.0934	0.1364	0.2786	0.101*
C15	0.70806 (15)	0.16822 (11)	0.07688 (17)	0.0619 (4)
H15A	0.6531	0.2213	0.0637	0.093*
H15B	0.7224	0.1444	0.1509	0.093*
H15C	0.6675	0.1219	0.0216	0.093*
C16	0.82499 (13)	0.35393 (9)	0.14503 (11)	0.0406 (3)
C17	0.79081 (14)	0.40931 (9)	0.05079 (11)	0.0435 (3)
H17	0.8174	0.3932	−0.0084	0.052*
C18	0.71800 (14)	0.48820 (9)	0.04184 (11)	0.0444 (3)
H18	0.6960	0.5246	−0.0225	0.053*
C19	0.67825 (13)	0.51235 (9)	0.12957 (11)	0.0433 (3)
C20	0.70878 (16)	0.45640 (11)	0.22319 (12)	0.0533 (4)
H20	0.6803	0.4715	0.2815	0.064*
C21	0.78103 (16)	0.37843 (10)	0.23047 (12)	0.0518 (4)
H21	0.8009	0.3413	0.2940	0.062*
C22	0.9119 (2)	0.42401 (13)	−0.40951 (16)	0.0748 (5)
H22A	0.8799	0.4276	−0.4903	0.112*
H22B	0.9946	0.4535	−0.3797	0.112*
H22C	0.8527	0.4543	−0.3813	0.112*
C23	0.58744 (18)	0.65403 (12)	0.04332 (15)	0.0655 (5)
H23A	0.5442	0.7070	0.0578	0.098*
H23B	0.5346	0.6263	−0.0265	0.098*
H23C	0.6685	0.6723	0.0386	0.098*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0733 (7)	0.0333 (5)	0.0769 (7)	−0.0017 (5)	0.0407 (6)	−0.0034 (5)
O2	0.096 (2)	0.140 (3)	0.085 (2)	0.0135 (19)	0.0052 (15)	−0.072 (2)
O2'	0.0510 (18)	0.085 (2)	0.156 (3)	−0.0229 (15)	0.0140 (18)	−0.046 (2)
O3	0.0798 (8)	0.0614 (7)	0.0550 (6)	0.0062 (6)	0.0265 (6)	0.0104 (5)
O4	0.0746 (7)	0.0486 (6)	0.0589 (6)	0.0254 (5)	0.0266 (5)	0.0045 (5)
N1	0.0411 (6)	0.0452 (6)	0.0437 (6)	−0.0008 (5)	0.0105 (5)	−0.0090 (5)
C2	0.0353 (6)	0.0446 (8)	0.0507 (7)	0.0034 (5)	0.0162 (6)	−0.0003 (6)
C3	0.0479 (8)	0.0426 (8)	0.0514 (8)	0.0141 (6)	0.0243 (6)	0.0085 (6)
C4	0.0526 (8)	0.0337 (7)	0.0423 (7)	0.0041 (6)	0.0244 (6)	0.0024 (5)
C5	0.0399 (6)	0.0335 (6)	0.0467 (7)	0.0032 (5)	0.0166 (5)	0.0013 (5)
C6	0.0479 (7)	0.0379 (7)	0.0366 (6)	0.0073 (6)	0.0173 (5)	0.0014 (5)
C7	0.0728 (13)	0.1154 (18)	0.0846 (14)	−0.0275 (13)	0.0205 (11)	−0.0533 (13)
C8	0.0373 (6)	0.0380 (7)	0.0518 (7)	0.0001 (5)	0.0227 (6)	0.0001 (6)
C9	0.0768 (11)	0.0344 (7)	0.0575 (9)	0.0039 (7)	0.0337 (8)	0.0006 (6)
C10	0.0841 (12)	0.0440 (8)	0.0535 (9)	0.0016 (8)	0.0330 (8)	−0.0051 (7)
C11	0.0452 (7)	0.0494 (8)	0.0525 (8)	0.0033 (6)	0.0242 (6)	0.0044 (6)
C12	0.0569 (9)	0.0368 (7)	0.0652 (9)	−0.0021 (6)	0.0264 (7)	0.0065 (7)
C13	0.0550 (8)	0.0379 (7)	0.0588 (8)	−0.0072 (6)	0.0237 (7)	−0.0043 (6)
C14	0.0601 (10)	0.0778 (12)	0.0615 (10)	0.0226 (9)	0.0179 (8)	0.0232 (9)
C15	0.0469 (8)	0.0496 (9)	0.0950 (13)	0.0020 (7)	0.0323 (8)	−0.0004 (8)
C16	0.0500 (7)	0.0346 (7)	0.0385 (6)	0.0058 (5)	0.0175 (5)	−0.0017 (5)
C17	0.0535 (8)	0.0428 (7)	0.0378 (6)	0.0063 (6)	0.0208 (6)	−0.0009 (5)
C18	0.0526 (8)	0.0398 (7)	0.0402 (7)	0.0050 (6)	0.0159 (6)	0.0042 (6)
C19	0.0473 (7)	0.0361 (7)	0.0460 (7)	0.0059 (6)	0.0160 (6)	−0.0032 (5)
C20	0.0732 (10)	0.0496 (9)	0.0462 (8)	0.0149 (7)	0.0324 (7)	0.0006 (6)
C21	0.0746 (10)	0.0454 (8)	0.0412 (7)	0.0165 (7)	0.0280 (7)	0.0066 (6)
C22	0.0856 (13)	0.0710 (12)	0.0707 (11)	0.0147 (10)	0.0316 (10)	0.0259 (9)
C23	0.0765 (11)	0.0466 (9)	0.0673 (10)	0.0210 (8)	0.0183 (9)	0.0075 (8)

Geometric parameters (Å, º) top

O1—C4	1.2067 (16)	C10—C11	1.380 (2)
O2—C7	1.182 (3)	C10—H10	0.93
O2'—C7	1.227 (4)	C11—C12	1.373 (2)
O3—C11	1.3642 (18)	C12—C13	1.384 (2)
O3—C22	1.421 (2)	C12—H12	0.93
O4—C19	1.3665 (16)	C13—H13	0.93
O4—C23	1.416 (2)	C14—H14A	0.96
N1—C7	1.337 (2)	C14—H14B	0.96
N1—C2	1.4743 (17)	C14—H14C	0.96
N1—C6	1.4803 (17)	C15—H15A	0.96
C2—C8	1.5183 (19)	C15—H15B	0.96
C2—C3	1.523 (2)	C15—H15C	0.96
C2—H2	0.98	C16—C17	1.3787 (18)
C3—C4	1.509 (2)	C16—C21	1.3865 (18)
C3—C14	1.533 (2)	C17—C18	1.3840 (19)
C3—H3	0.98	C17—H17	0.93
C4—C5	1.5111 (18)	C18—C19	1.3829 (19)
C5—C15	1.521 (2)	C18—H18	0.93
C5—C6	1.5302 (18)	C19—C20	1.379 (2)
C5—H5	0.98	C20—C21	1.372 (2)
C6—C16	1.5145 (18)	C20—H20	0.93
C6—H6	0.98	C21—H21	0.93
C7—H7	0.93	C22—H22A	0.96
C7—H7'	0.96	C22—H22B	0.96
C8—C13	1.385 (2)	C22—H22C	0.96
C8—C9	1.387 (2)	C23—H23A	0.96
C9—C10	1.372 (2)	C23—H23B	0.96
C9—H9	0.93	C23—H23C	0.96

C11—O3—C22	117.82 (13)	C12—C11—C10	118.99 (14)
C19—O4—C23	117.70 (12)	C11—C12—C13	119.53 (14)
C7—N1—C2	119.66 (14)	C11—C12—H12	120.2
C7—N1—C6	118.59 (14)	C13—C12—H12	120.2
C2—N1—C6	119.80 (10)	C12—C13—C8	122.36 (14)
N1—C2—C8	112.33 (11)	C12—C13—H13	118.8
N1—C2—C3	108.39 (11)	C8—C13—H13	118.8
C8—C2—C3	115.34 (12)	C3—C14—H14A	109.5
N1—C2—H2	106.8	C3—C14—H14B	109.5
C8—C2—H2	106.8	H14A—C14—H14B	109.5
C3—C2—H2	106.8	C3—C14—H14C	109.5
C4—C3—C2	110.75 (11)	H14A—C14—H14C	109.5
C4—C3—C14	108.56 (12)	H14B—C14—H14C	109.5
C2—C3—C14	112.39 (13)	C5—C15—H15A	109.5
C4—C3—H3	108.3	C5—C15—H15B	109.5
C2—C3—H3	108.3	H15A—C15—H15B	109.5
C14—C3—H3	108.3	C5—C15—H15C	109.5
O1—C4—C3	121.28 (12)	H15A—C15—H15C	109.5
O1—C4—C5	121.92 (13)	H15B—C15—H15C	109.5
C3—C4—C5	116.79 (11)	C17—C16—C21	117.74 (12)
C4—C5—C15	111.63 (11)	C17—C16—C6	122.14 (11)
C4—C5—C6	111.35 (11)	C21—C16—C6	120.11 (12)
C15—C5—C6	111.25 (12)	C16—C17—C18	121.77 (12)
C4—C5—H5	107.5	C16—C17—H17	119.1
C15—C5—H5	107.5	C18—C17—H17	119.1
C6—C5—H5	107.5	C19—C18—C17	119.31 (12)
N1—C6—C16	111.47 (11)	C19—C18—H18	120.3
N1—C6—C5	110.78 (10)	C17—C18—H18	120.3
C16—C6—C5	112.22 (10)	O4—C19—C20	115.68 (12)
N1—C6—H6	107.4	O4—C19—C18	124.68 (12)
C16—C6—H6	107.4	C20—C19—C18	119.63 (12)
C5—C6—H6	107.4	C21—C20—C19	120.17 (12)
O2—C7—O2'	109.5 (3)	C21—C20—H20	119.9
O2—C7—N1	124.4 (3)	C19—C20—H20	119.9
O2'—C7—N1	126.1 (3)	C20—C21—C16	121.34 (13)
O2—C7—H7	117.8	C20—C21—H21	119.3
N1—C7—H7	117.8	C16—C21—H21	119.3
O2'—C7—H7'	116.8	O3—C22—H22A	109.5
N1—C7—H7'	117.2	O3—C22—H22B	109.5
C13—C8—C9	116.86 (13)	H22A—C22—H22B	109.5
C13—C8—C2	120.31 (12)	O3—C22—H22C	109.5
C9—C8—C2	122.79 (12)	H22A—C22—H22C	109.5
C10—C9—C8	121.23 (14)	H22B—C22—H22C	109.5
C10—C9—H9	119.4	O4—C23—H23A	109.5
C8—C9—H9	119.4	O4—C23—H23B	109.5
C9—C10—C11	121.01 (14)	H23A—C23—H23B	109.5
C9—C10—H10	119.5	O4—C23—H23C	109.5
C11—C10—H10	119.5	H23A—C23—H23C	109.5
O3—C11—C12	125.11 (13)	H23B—C23—H23C	109.5
O3—C11—C10	115.89 (13)

C7—N1—C2—C8	−109.80 (19)	N1—C2—C8—C9	−140.48 (13)
C6—N1—C2—C8	86.30 (14)	C3—C2—C8—C9	−15.60 (18)
C7—N1—C2—C3	121.58 (18)	C13—C8—C9—C10	−1.5 (2)
C6—N1—C2—C3	−42.33 (16)	C2—C8—C9—C10	−179.28 (14)
N1—C2—C3—C4	58.59 (14)	C8—C9—C10—C11	0.5 (3)
C8—C2—C3—C4	−68.32 (14)	C22—O3—C11—C12	0.1 (2)
N1—C2—C3—C14	−63.02 (15)	C22—O3—C11—C10	178.86 (15)
C8—C2—C3—C14	170.07 (11)	C9—C10—C11—O3	−177.91 (14)
C2—C3—C4—O1	160.79 (13)	C9—C10—C11—C12	0.9 (2)
C14—C3—C4—O1	−75.37 (17)	O3—C11—C12—C13	177.39 (14)
C2—C3—C4—C5	−20.74 (16)	C10—C11—C12—C13	−1.3 (2)
C14—C3—C4—C5	103.09 (14)	C11—C12—C13—C8	0.3 (2)
O1—C4—C5—C15	19.05 (19)	C9—C8—C13—C12	1.1 (2)
C3—C4—C5—C15	−159.40 (12)	C2—C8—C13—C12	178.93 (13)
O1—C4—C5—C6	144.05 (13)	N1—C6—C16—C17	60.77 (17)
C3—C4—C5—C6	−34.40 (15)	C5—C6—C16—C17	−64.16 (17)
C7—N1—C6—C16	57.6 (2)	N1—C6—C16—C21	−120.35 (14)
C2—N1—C6—C16	−138.34 (12)	C5—C6—C16—C21	114.73 (15)
C7—N1—C6—C5	−176.69 (17)	C21—C16—C17—C18	1.7 (2)
C2—N1—C6—C5	−12.62 (16)	C6—C16—C17—C18	−179.42 (13)
C4—C5—C6—N1	51.38 (14)	C16—C17—C18—C19	0.0 (2)
C15—C5—C6—N1	176.60 (11)	C23—O4—C19—C20	173.65 (15)
C4—C5—C6—C16	176.69 (10)	C23—O4—C19—C18	−5.9 (2)
C15—C5—C6—C16	−58.09 (15)	C17—C18—C19—O4	177.91 (13)
C2—N1—C7—O2	−150.5 (3)	C17—C18—C19—C20	−1.7 (2)
C6—N1—C7—O2	13.6 (4)	O4—C19—C20—C21	−177.95 (15)
C2—N1—C7—O2'	32.2 (4)	C18—C19—C20—C21	1.7 (2)
C6—N1—C7—O2'	−163.7 (3)	C19—C20—C21—C16	0.0 (3)
N1—C2—C8—C13	41.78 (17)	C17—C16—C21—C20	−1.7 (2)
C3—C2—C8—C13	166.66 (12)	C6—C16—C21—C20	179.39 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.98	2.48	3.429 (2)	163
C15—H15C···O2ⁱⁱ	0.96	2.53	3.240 (4)	131
C20—H20···O1ⁱⁱⁱ	0.93	2.51	3.432 (2)	171

Symmetry codes: (i) −x+2, −y, −z; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+3/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₅NO₄
M_r	367.43
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	11.0954 (4), 14.5407 (3), 12.7050 (4)
β (°)	110.977 (1)
V (Å³)	1913.91 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.974, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	24720, 5524, 3703
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.702

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.140, 1.05
No. of reflections	5524
No. of parameters	256
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.23

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), 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
C3—H3···O1ⁱ	0.98	2.48	3.429 (2)	163
C15—H15C···O2ⁱⁱ	0.96	2.53	3.240 (4)	131
C20—H20···O1ⁱⁱⁱ	0.93	2.51	3.432 (2)	171

Symmetry codes: (i) −x+2, −y, −z; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+3/2, y+1/2, −z+1/2.

Acknowledgements

TK thanks Dr Babu Varghese, SAIF, IIT-Madras, Chennai, India, for his help with the data collection. SP thanks the UGC, India, for financial support.

References

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