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

Kavitha, T.; Ponnuswamy, S.; Sakthivel, P.; Karthik, K.; Ponnuswamy, M.N.

doi:10.1107/S1600536809010010

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o856

doi:10.1107/S1600536809010010

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

T. Kavitha,^a S. Ponnuswamy,^b P. Sakthivel,^b K. Karthik ^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, Tamilnadu, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 13 March 2009; accepted 18 March 2009; online 25 March 2009)

In the title compound, C₂₂H₂₅NO₄, the piperidine ring adopts a distorted boat conformation. The two benzene rings are approximately perpendicular to each other, making a dihedral angle of 86.2 (8)°. The crystal packing is stabilized by C—H⋯O and C—H⋯π interactions.

Related literature

For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ). For ring conformational analysis, see: Cremer & Pople (1975 ); Nardelli (1983 ).

Experimental

Crystal data

C₂₂H₂₅NO₄
M_r = 367.43
Monoclinic, P 2₁ /c
a = 11.7274 (3) Å
b = 18.8556 (4) Å
c = 9.7178 (3) Å
β = 113.507 (1)°
V = 1970.54 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.25 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.979, T_max = 0.983
26804 measured reflections
6250 independent reflections
4080 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.142
S = 1.03
6250 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O3ⁱ	0.97	2.44	3.3446 (16)	155
C6—H6⋯O2ⁱⁱ	0.98	2.41	3.3708 (16)	168
C18—H18⋯O1ⁱⁱⁱ	0.93	2.53	3.3018 (17)	140
C10—H10⋯Cg1^iv	0.93	2.90	3.6627 (17)	140
Symmetry codes: (i) x, y, z-1; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z+1; (iv) -x+1, -y, -z+2. Cg(1) is the centroid of the C16–C21 ring.

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: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1983).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809010010/bt2903sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809010010/bt2903Isup2.hkl

checkCIF report

Comment top

Piperidine, a basic component of the piper alkaloid piper nigrum is a monocyclic cyclohexane with a hetero atom affixed in the first position. The skeletal ring of piperidine is contained in the molecules of many synthetic and natural medicaments. A significant industrial application of piperidine is for the production of dipiperidinyl dithiuram tetrasulfide, which can be used as a rubber vulcanization accelerator.

The piperidine ring adopts distorted boat conformation with puckering parameters (Cremer & Pople, 1975) q2 = 0.630 (1) Å, q3 =0.070 (1)Å and ϕ2= 87.2 (1)° and the asymmetry parameters ΔC₂(N1) and ΔC₂(C4) = 14.78 (12)Å (Nardelli, 1983). The angles between the best plane of the piperidine ring (N1,C3,C4,C6) and the phenyl rings (C8—C13 and C16—C21) are 84.17 (7)° and 80.70 (7)°, respectively. The two phenyl rings are approximately perpendicular to each other as can be seen from the dihedral angle of 86.23 (8)°. The methyl substituents C14 and C15 are oriented equatorially [N1—C2—C3—C14 =] -178.88 (11)° and axially [N1—C2—C3—C15 =] -59.52 (13) ° with respect to the piperidine ring. The sum of the bond angles around N1 atom (359.3°) indicates sp² hybridization.

The packing of the molecules is controlled by C—H···O types of intermolecular interactions. The symmetry related molecules form a dimer with the graph-set motif of R²₂(16) (Bernstein et al., 1995) through hydrogen bonds. Further a C—H··· π interaction also leads to the formation of a dimer [C10—H10 = 0.9301 Å, H10···Cg(1) =2.9035 Å, C10···Cg(1) = 3.6627 (17) Å and C10—H10···Cg(1) = 139.71°, where Cg(1) is the centroid of the ring (C16—C21) at (1 - x,-y,2 - z)] .

Related literature top

For details of hydrogen-bond motifs, see: Bernstein et al. (1995). For ring conformational analysis, see: Cremer & Pople (1975); Nardelli (1983). Cg(1) is the centroid of the C16–C21 ring.

Experimental top

The 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)-c-3,t-3-dimethylpiperidine-4-one (1.69 g) in benzene (30 ml). The reaction mixture was stirred at room temperature for 5 hrs. 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.

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: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PARST (Nardelli, 1983).

Figures top

	Fig. 1. ORTEP plot of the molecule showing that the thermal ellipsoids are drawn at 30% probability level. H atoms have been omitted for clarity.
	Fig. 2. The molecular packing of the compound viewed down the b axis is shown. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted.

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

Crystal data top

C₂₂H₂₅NO₄	F(000) = 784
M_r = 367.43	D_x = 1.239 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6250 reflections
a = 11.7274 (3) Å	θ = 2.2–31.0°
b = 18.8556 (4) Å	µ = 0.09 mm⁻¹
c = 9.7178 (3) Å	T = 293 K
β = 113.507 (1)°	Block, colourless
V = 1970.54 (9) Å³	0.25 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII diffractometer	6250 independent reflections
Radiation source: fine-focus sealed tube	4080 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω and ϕ scans	θ_max = 31.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −16→16
T_min = 0.979, T_max = 0.983	k = −27→26
26804 measured reflections	l = −14→14

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0615P)² + 0.3342P] where P = (F_o² + 2F_c²)/3
6250 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₂H₂₅NO₄	V = 1970.54 (9) Å³
M_r = 367.43	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.7274 (3) Å	µ = 0.09 mm⁻¹
b = 18.8556 (4) Å	T = 293 K
c = 9.7178 (3) Å	0.25 × 0.20 × 0.20 mm
β = 113.507 (1)°

Data collection top

Bruker Kappa APEXII diffractometer	6250 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	4080 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.983	R_int = 0.031
26804 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.142	H-atom parameters constrained
S = 1.03	Δρ_max = 0.23 e Å⁻³
6250 reflections	Δρ_min = −0.19 e Å⁻³
244 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
C2	0.17408 (11)	0.62041 (6)	0.40308 (14)	0.0338 (3)
H2	0.1120	0.6538	0.4087	0.041*
C3	0.10682 (11)	0.57637 (7)	0.25999 (14)	0.0381 (3)
C4	0.19953 (12)	0.53109 (7)	0.22723 (13)	0.0363 (3)
C5	0.33023 (12)	0.55897 (7)	0.27795 (15)	0.0366 (3)
H5A	0.3623	0.5459	0.2036	0.044*
H5B	0.3812	0.5353	0.3709	0.044*
C6	0.34585 (11)	0.63892 (6)	0.30324 (13)	0.0323 (2)
H6	0.3138	0.6621	0.2048	0.039*
C7	0.28230 (12)	0.73249 (7)	0.42790 (15)	0.0398 (3)
H7	0.3400	0.7599	0.4081	0.048*
C8	0.22360 (11)	0.58092 (7)	0.55153 (14)	0.0352 (3)
C9	0.26574 (13)	0.51168 (7)	0.57097 (15)	0.0429 (3)
H9	0.2638	0.4863	0.4880	0.052*
C10	0.31075 (14)	0.47894 (8)	0.70986 (16)	0.0446 (3)
H10	0.3396	0.4325	0.7196	0.054*
C11	0.31275 (14)	0.51526 (8)	0.83330 (15)	0.0446 (3)
C12	0.26964 (16)	0.58424 (8)	0.81650 (17)	0.0530 (4)
H12	0.2700	0.6092	0.8993	0.064*
C13	0.22628 (14)	0.61613 (8)	0.67819 (16)	0.0462 (3)
H13	0.1979	0.6627	0.6690	0.055*
C14	0.00369 (14)	0.53174 (9)	0.2744 (2)	0.0553 (4)
H14A	−0.0532	0.5621	0.2953	0.083*
H14B	0.0393	0.4983	0.3548	0.083*
H14C	−0.0400	0.5067	0.1822	0.083*
C15	0.04780 (14)	0.62642 (8)	0.12465 (17)	0.0513 (4)
H15A	−0.0123	0.6563	0.1401	0.077*
H15B	0.0076	0.5989	0.0351	0.077*
H15C	0.1114	0.6553	0.1143	0.077*
C16	0.48138 (11)	0.65875 (6)	0.38343 (14)	0.0332 (3)
C17	0.55115 (11)	0.63584 (7)	0.52784 (14)	0.0368 (3)
H17	0.5134	0.6082	0.5770	0.044*
C18	0.67579 (12)	0.65292 (7)	0.60132 (16)	0.0418 (3)
H18	0.7212	0.6366	0.6982	0.050*
C19	0.73163 (13)	0.69426 (8)	0.52933 (19)	0.0511 (4)
C20	0.66322 (15)	0.71813 (10)	0.3859 (2)	0.0623 (5)
H20	0.7008	0.7464	0.3375	0.075*
C21	0.53942 (14)	0.70045 (8)	0.31376 (17)	0.0488 (4)
H21	0.4943	0.7168	0.2168	0.059*
C22	0.3775 (2)	0.41457 (10)	0.9928 (2)	0.0736 (5)
H22A	0.4042	0.4023	1.0969	0.110*
H22B	0.4416	0.4027	0.9590	0.110*
H22C	0.3032	0.3887	0.9349	0.110*
C23	0.92890 (16)	0.68961 (11)	0.7357 (3)	0.0787 (6)
H23A	1.0117	0.7079	0.7651	0.118*
H23B	0.9311	0.6387	0.7350	0.118*
H23C	0.8951	0.7053	0.8056	0.118*
N1	0.27207 (9)	0.66443 (5)	0.38626 (11)	0.0321 (2)
O1	0.17227 (10)	0.47451 (5)	0.16419 (12)	0.0515 (3)
O2	0.22263 (10)	0.76191 (5)	0.48956 (13)	0.0524 (3)
O3	0.35310 (13)	0.48797 (6)	0.97457 (12)	0.0646 (3)
O4	0.85343 (11)	0.71456 (8)	0.59033 (17)	0.0816 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0292 (5)	0.0337 (6)	0.0364 (6)	−0.0019 (5)	0.0109 (5)	−0.0052 (5)
C3	0.0320 (6)	0.0379 (6)	0.0374 (7)	−0.0076 (5)	0.0065 (5)	−0.0049 (5)
C4	0.0435 (7)	0.0340 (6)	0.0260 (6)	−0.0071 (5)	0.0080 (5)	−0.0030 (5)
C5	0.0382 (6)	0.0353 (6)	0.0354 (6)	−0.0023 (5)	0.0137 (5)	−0.0077 (5)
C6	0.0317 (6)	0.0327 (6)	0.0288 (6)	−0.0019 (5)	0.0081 (5)	−0.0006 (4)
C7	0.0364 (6)	0.0301 (6)	0.0448 (7)	−0.0007 (5)	0.0076 (6)	−0.0040 (5)
C8	0.0340 (6)	0.0369 (6)	0.0361 (6)	−0.0041 (5)	0.0155 (5)	−0.0055 (5)
C9	0.0548 (8)	0.0413 (7)	0.0374 (7)	0.0031 (6)	0.0234 (6)	−0.0050 (5)
C10	0.0556 (8)	0.0411 (7)	0.0425 (7)	0.0052 (6)	0.0252 (7)	0.0025 (6)
C11	0.0527 (8)	0.0492 (8)	0.0360 (7)	−0.0079 (6)	0.0220 (6)	−0.0009 (6)
C12	0.0787 (11)	0.0465 (8)	0.0418 (8)	−0.0045 (7)	0.0323 (8)	−0.0108 (6)
C13	0.0609 (9)	0.0382 (7)	0.0454 (8)	−0.0004 (6)	0.0275 (7)	−0.0072 (6)
C14	0.0413 (8)	0.0585 (9)	0.0620 (10)	−0.0193 (7)	0.0162 (7)	−0.0103 (8)
C15	0.0406 (7)	0.0506 (8)	0.0431 (8)	−0.0029 (6)	−0.0039 (6)	−0.0003 (6)
C16	0.0305 (5)	0.0305 (6)	0.0351 (6)	−0.0017 (4)	0.0094 (5)	0.0001 (5)
C17	0.0337 (6)	0.0379 (6)	0.0359 (6)	−0.0024 (5)	0.0108 (5)	0.0017 (5)
C18	0.0347 (6)	0.0400 (7)	0.0406 (7)	0.0003 (5)	0.0042 (5)	−0.0002 (5)
C19	0.0328 (7)	0.0457 (8)	0.0640 (10)	−0.0071 (6)	0.0081 (7)	0.0027 (7)
C20	0.0453 (8)	0.0647 (10)	0.0719 (11)	−0.0151 (7)	0.0182 (8)	0.0234 (9)
C21	0.0437 (8)	0.0492 (8)	0.0470 (8)	−0.0054 (6)	0.0113 (6)	0.0152 (6)
C22	0.1037 (15)	0.0640 (11)	0.0502 (10)	0.0027 (10)	0.0277 (10)	0.0144 (8)
C23	0.0342 (8)	0.0782 (13)	0.0957 (15)	−0.0048 (8)	−0.0036 (9)	0.0030 (11)
N1	0.0293 (5)	0.0279 (5)	0.0341 (5)	−0.0019 (4)	0.0076 (4)	−0.0031 (4)
O1	0.0621 (6)	0.0396 (5)	0.0481 (6)	−0.0136 (5)	0.0169 (5)	−0.0155 (4)
O2	0.0531 (6)	0.0367 (5)	0.0643 (7)	0.0024 (4)	0.0204 (5)	−0.0136 (5)
O3	0.1002 (9)	0.0585 (7)	0.0396 (6)	0.0004 (6)	0.0326 (6)	0.0052 (5)
O4	0.0371 (6)	0.0867 (9)	0.0976 (10)	−0.0224 (6)	0.0023 (6)	0.0220 (8)

Geometric parameters (Å, º) top

C2—N1	1.4785 (15)	C12—H12	0.9300
C2—C8	1.5181 (18)	C13—H13	0.9300
C2—C3	1.5395 (17)	C14—H14A	0.9600
C2—H2	0.9800	C14—H14B	0.9600
C3—C4	1.5128 (19)	C14—H14C	0.9600
C3—C14	1.5250 (19)	C15—H15A	0.9600
C3—C15	1.541 (2)	C15—H15B	0.9600
C4—O1	1.2081 (15)	C15—H15C	0.9600
C4—C5	1.5053 (18)	C16—C21	1.3811 (18)
C5—C6	1.5267 (17)	C16—C17	1.3818 (17)
C5—H5A	0.9700	C17—C18	1.3847 (18)
C5—H5B	0.9700	C17—H17	0.9300
C6—N1	1.4791 (15)	C18—C19	1.375 (2)
C6—C16	1.5117 (16)	C18—H18	0.9300
C6—H6	0.9800	C19—O4	1.3648 (17)
C7—O2	1.2211 (17)	C19—C20	1.377 (2)
C7—N1	1.3365 (16)	C20—C21	1.378 (2)
C7—H7	0.9300	C20—H20	0.9300
C8—C9	1.3821 (18)	C21—H21	0.9300
C8—C13	1.3877 (18)	C22—O3	1.410 (2)
C9—C10	1.3831 (19)	C22—H22A	0.9600
C9—H9	0.9300	C22—H22B	0.9600
C10—C11	1.3734 (19)	C22—H22C	0.9600
C10—H10	0.9300	C23—O4	1.415 (2)
C11—O3	1.3621 (17)	C23—H23A	0.9600
C11—C12	1.381 (2)	C23—H23B	0.9600
C12—C13	1.372 (2)	C23—H23C	0.9600

N1—C2—C8	111.15 (9)	C3—C14—H14A	109.5
N1—C2—C3	110.11 (10)	C3—C14—H14B	109.5
C8—C2—C3	117.24 (10)	H14A—C14—H14B	109.5
N1—C2—H2	105.8	C3—C14—H14C	109.5
C8—C2—H2	105.8	H14A—C14—H14C	109.5
C3—C2—H2	105.8	H14B—C14—H14C	109.5
C4—C3—C14	111.76 (11)	C3—C15—H15A	109.5
C4—C3—C2	110.01 (10)	C3—C15—H15B	109.5
C14—C3—C2	110.73 (11)	H15A—C15—H15B	109.5
C4—C3—C15	106.37 (11)	C3—C15—H15C	109.5
C14—C3—C15	108.28 (12)	H15A—C15—H15C	109.5
C2—C3—C15	109.55 (11)	H15B—C15—H15C	109.5
O1—C4—C5	120.22 (12)	C21—C16—C17	117.89 (12)
O1—C4—C3	122.55 (12)	C21—C16—C6	120.70 (11)
C5—C4—C3	117.22 (10)	C17—C16—C6	121.41 (11)
C4—C5—C6	116.02 (11)	C16—C17—C18	121.78 (12)
C4—C5—H5A	108.3	C16—C17—H17	119.1
C6—C5—H5A	108.3	C18—C17—H17	119.1
C4—C5—H5B	108.3	C19—C18—C17	119.24 (13)
C6—C5—H5B	108.3	C19—C18—H18	120.4
H5A—C5—H5B	107.4	C17—C18—H18	120.4
N1—C6—C16	111.21 (9)	O4—C19—C18	124.49 (15)
N1—C6—C5	110.49 (10)	O4—C19—C20	115.74 (14)
C16—C6—C5	111.18 (10)	C18—C19—C20	119.77 (13)
N1—C6—H6	107.9	C19—C20—C21	120.42 (14)
C16—C6—H6	107.9	C19—C20—H20	119.8
C5—C6—H6	107.9	C21—C20—H20	119.8
O2—C7—N1	125.80 (13)	C20—C21—C16	120.90 (14)
O2—C7—H7	117.1	C20—C21—H21	119.6
N1—C7—H7	117.1	C16—C21—H21	119.6
C9—C8—C13	116.76 (12)	O3—C22—H22A	109.5
C9—C8—C2	125.00 (11)	O3—C22—H22B	109.5
C13—C8—C2	118.23 (12)	H22A—C22—H22B	109.5
C8—C9—C10	122.10 (12)	O3—C22—H22C	109.5
C8—C9—H9	118.9	H22A—C22—H22C	109.5
C10—C9—H9	118.9	H22B—C22—H22C	109.5
C11—C10—C9	119.78 (13)	O4—C23—H23A	109.5
C11—C10—H10	120.1	O4—C23—H23B	109.5
C9—C10—H10	120.1	H23A—C23—H23B	109.5
O3—C11—C10	124.75 (14)	O4—C23—H23C	109.5
O3—C11—C12	116.01 (12)	H23A—C23—H23C	109.5
C10—C11—C12	119.23 (13)	H23B—C23—H23C	109.5
C13—C12—C11	120.24 (13)	C7—N1—C2	119.04 (10)
C13—C12—H12	119.9	C7—N1—C6	118.42 (10)
C11—C12—H12	119.9	C2—N1—C6	121.82 (9)
C12—C13—C8	121.86 (13)	C11—O3—C22	117.96 (12)
C12—C13—H13	119.1	C19—O4—C23	118.02 (14)
C8—C13—H13	119.1

N1—C2—C3—C4	57.08 (13)	C2—C8—C13—C12	−179.98 (13)
C8—C2—C3—C4	−71.28 (13)	N1—C6—C16—C21	−120.55 (13)
N1—C2—C3—C14	−178.88 (11)	C5—C6—C16—C21	115.87 (14)
C8—C2—C3—C14	52.76 (15)	N1—C6—C16—C17	59.60 (15)
N1—C2—C3—C15	−59.52 (13)	C5—C6—C16—C17	−63.98 (15)
C8—C2—C3—C15	172.12 (11)	C21—C16—C17—C18	−0.8 (2)
C14—C3—C4—O1	26.68 (18)	C6—C16—C17—C18	179.06 (12)
C2—C3—C4—O1	150.13 (12)	C16—C17—C18—C19	0.5 (2)
C15—C3—C4—O1	−91.31 (15)	C17—C18—C19—O4	179.89 (15)
C14—C3—C4—C5	−152.76 (12)	C17—C18—C19—C20	0.1 (2)
C2—C3—C4—C5	−29.32 (15)	O4—C19—C20—C21	179.76 (17)
C15—C3—C4—C5	89.25 (13)	C18—C19—C20—C21	−0.4 (3)
O1—C4—C5—C6	158.68 (12)	C19—C20—C21—C16	0.2 (3)
C3—C4—C5—C6	−21.86 (16)	C17—C16—C21—C20	0.4 (2)
C4—C5—C6—N1	44.33 (14)	C6—C16—C21—C20	−179.41 (15)
C4—C5—C6—C16	168.32 (10)	O2—C7—N1—C2	5.3 (2)
N1—C2—C8—C9	−96.55 (14)	O2—C7—N1—C6	175.84 (12)
C3—C2—C8—C9	31.31 (17)	C8—C2—N1—C7	−93.80 (13)
N1—C2—C8—C13	84.08 (14)	C3—C2—N1—C7	134.58 (12)
C3—C2—C8—C13	−148.07 (12)	C8—C2—N1—C6	96.04 (12)
C13—C8—C9—C10	−1.2 (2)	C3—C2—N1—C6	−35.59 (14)
C2—C8—C9—C10	179.46 (13)	C16—C6—N1—C7	51.11 (14)
C8—C9—C10—C11	0.9 (2)	C5—C6—N1—C7	175.08 (11)
C9—C10—C11—O3	178.92 (14)	C16—C6—N1—C2	−138.67 (11)
C9—C10—C11—C12	−0.1 (2)	C5—C6—N1—C2	−14.70 (15)
O3—C11—C12—C13	−179.56 (15)	C10—C11—O3—C22	−9.8 (2)
C10—C11—C12—C13	−0.5 (2)	C12—C11—O3—C22	169.20 (16)
C11—C12—C13—C8	0.2 (2)	C18—C19—O4—C23	2.2 (3)
C9—C8—C13—C12	0.6 (2)	C20—C19—O4—C23	−178.04 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O3ⁱ	0.97	2.44	3.3446 (16)	155
C6—H6···O2ⁱⁱ	0.98	2.41	3.3708 (16)	168
C18—H18···O1ⁱⁱⁱ	0.93	2.53	3.3018 (17)	140
C10—H10···Cg1^iv	0.93	2.90	3.6627 (17)	140

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

Experimental details

Crystal data
Chemical formula	C₂₂H₂₅NO₄
M_r	367.43
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.7274 (3), 18.8556 (4), 9.7178 (3)
β (°)	113.507 (1)
V (Å³)	1970.54 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.979, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	26804, 6250, 4080
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.725

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.142, 1.03
No. of reflections	6250
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.19

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and PARST (Nardelli, 1983).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O3ⁱ	0.97	2.44	3.3446 (16)	154.6
C6—H6···O2ⁱⁱ	0.98	2.41	3.3708 (16)	168.1
C18—H18···O1ⁱⁱⁱ	0.93	2.53	3.3018 (17)	140.4
C10—H10···Cg1^iv	0.93	2.90	3.6627 (17)	139.7

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

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 (2004). SAINT and APEX2. 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
Nardelli, M. (1983). Acta Cryst. C39, 1141–1142. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany. 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