4,9-Dioxa-1,3(1,2)-dibenzena-2(4,5)-1,3-oxazolidinacyclononaphane

Balakrishnan, B.; Seshadri, P.R.; Purushothaman, S.; Raghunathan, R.

doi:10.1107/S1600536810052517

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o469

doi:10.1107/S1600536810052517

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4,9-Dioxa-1,3(1,2)-dibenzena-2(4,5)-1,3-oxazolidinacyclononaphane

B. Balakrishnan,^a P. R. Seshadri,^b ^* S. Purushothaman ^c and R. Raghunathan ^c

^aDepartment of Physics, P. T. Lee Chengalvaraya Naicker College of Engineering & Technology, Kancheepuram 631 502, India, ^bPostGraduate & Research Department of Physics, Agurchand Manmull Jain College, Chennai 600 114, India, and ^cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: seshadri_pr@yahoo.com

(Received 30 November 2010; accepted 14 December 2010; online 22 January 2011)

The oxazole ring in the title compound, C₂₀H₂₃NO₃, adopts an envelope conformation while the 12-membered ring is in a chair conformation. The dihedral angle between the benzene rings is 37.8 (1)°. The crystal structure displays intermolecular C—H⋯O hydrogen bonding.

Related literature

For general background to cyclophanes and 1,3-dipolar cycloaddition reactions, see: Whelligan et al. (2006 ); Poornachandran et al. (2008 ). For the chemistry of azomethine ylides, see; Longeon et al. (1990 ). For descriptions of ring conformations, see: Cremer & Pople (1975 ); Nardelli (1983 ).

Experimental

Crystal data

C₂₀H₂₃NO₃
M_r = 325.39
Monoclinic, P 2₁ /c
a = 9.5193 (7) Å
b = 13.0996 (8) Å
c = 13.6000 (9) Å
β = 96.704 (3)°
V = 1684.3 (2) 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 area-detector diffractometer
33618 measured reflections
3864 independent reflections
2937 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.146
S = 1.02
3864 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.30 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
C14—H14⋯O1ⁱ	0.93	2.56	3.396 (2)	150
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810052517/bt5428sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810052517/bt5428Isup2.hkl

checkCIF report

Comment top

Cyclophanes can act as a ligand in asymmetric catalysis (Whelligan et al., 2006) and can as host molecules for the incorporation of guest molecules or ions. 1,3-dipolar cycloaddition (1,3-DC) reactions are efficient methods for the construction of heterocyclic units in a highly regio- and stereoselective manner (Poornachandran et al., 2008). In particular the chemistry of azomethine ylides has gained importance in recent years as it serves as an expedient route for the construction of nitrogen heterocycles (Longeon et al., 1990).

In the crystal structure of the title compound the oxazole ring is twisted along N1 - C9 and adopts an envelope conformation with the atom C9 displaced by -0.360 (0) \%A from the plane of the other ring atoms N1/O1//C7/C8. The puckering parameters (Cremer & Pople, 1975) and asymmetry parameters (Nardelli, 1983) are q~2~ =0.388 (2) Å, ϕ = 130.5 (2)°, Δ~S~ (C9) = 0.073 (1)° and Δ~2~ (C9) = 0.223 (1)°. In addition to van der Waals interactions the crystal structure is stabilized by C—H···O, hydrogen bonds.

Related literature top

For general background to cyclophanes and 1,3-dipolar cycloaddition reactions, see: Whelligan et al. (2006); Poornachandran et al. (2008). For the chemistry of azomethine ylides, see; Longeon et al. (1990). For descriptions of ring conformations, see: Cremer & Pople (1975); Nardelli (1983).

Experimental top

A solution of O,O' coupled salicylaldehyde (bis aldehyde) using 1,4-dibromobutane (2 mmol) and sarcosine 2 (1 eq.) was refluxed in dry acetonitrile (20 ml) for about 6hrs under N2 atm. After the completion of reaction as indicated by TLC, acetonitrile was evaporated under reduced pressure.The crude product was purified by column chromatography using hexane: EtOAc (8:2) as eluent.

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

Figures top

Fig. 1. Molecular structure of the title compound, showing 30% probability displacement ellipsoids.

5-methyl-3,13,18-trioxa-5-azatetracyclo[17.4.0.0^2,6.07,12]tricosa- 1(19),7,9,11,20,22-hexaene top

Crystal data top

C₂₀H₂₃NO₃	F(000) = 696
M_r = 325.39	D_x = 1.283 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.5193 (7) Å	Cell parameters from 5405 reflections
b = 13.0996 (8) Å	θ = 2.2–27.5°
c = 13.6000 (9) Å	µ = 0.09 mm⁻¹
β = 96.704 (3)°	T = 293 K
V = 1684.3 (2) Å³	Block, colourless
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker Kappa APEXII area-detector diffractometer	2937 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.053
Graphite monochromator	θ_max = 27.5°, θ_min = 2.2°
ω scans	h = −12→12
33618 measured reflections	k = −17→11
3864 independent 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0761P)² + 0.5036P] where P = (F_o² + 2F_c²)/3
3864 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₀H₂₃NO₃	V = 1684.3 (2) Å³
M_r = 325.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.5193 (7) Å	µ = 0.09 mm⁻¹
b = 13.0996 (8) Å	T = 293 K
c = 13.6000 (9) Å	0.30 × 0.20 × 0.20 mm
β = 96.704 (3)°

Data collection top

Bruker Kappa APEXII area-detector diffractometer	2937 reflections with I > 2σ(I)
33618 measured reflections	R_int = 0.053
3864 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.02	Δρ_max = 0.30 e Å⁻³
3864 reflections	Δρ_min = −0.19 e Å⁻³
218 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	1.03220 (16)	0.21959 (11)	0.36089 (11)	0.0333 (3)
C2	1.17864 (17)	0.22294 (13)	0.37457 (13)	0.0425 (4)
H2	1.2308	0.1756	0.3431	0.051*
C3	1.24706 (18)	0.29660 (15)	0.43489 (15)	0.0501 (4)
H3	1.3454	0.2989	0.4436	0.060*
C4	1.17130 (19)	0.36634 (14)	0.48207 (14)	0.0507 (5)
H4	1.2177	0.4161	0.5224	0.061*
C5	1.02488 (18)	0.36210 (13)	0.46926 (13)	0.0420 (4)
H5	0.9736	0.4091	0.5019	0.050*
C6	0.95331 (15)	0.28944 (11)	0.40890 (11)	0.0324 (3)
C7	0.79349 (16)	0.28849 (11)	0.39086 (12)	0.0347 (3)
H7	0.7647	0.2910	0.3193	0.042*
C8	0.72211 (15)	0.19497 (11)	0.43422 (11)	0.0328 (3)
H8	0.7910	0.1597	0.4817	0.039*
C9	0.6768 (2)	0.33945 (15)	0.51895 (15)	0.0530 (5)
H9A	0.6059	0.3865	0.5377	0.064*
H9B	0.7489	0.3302	0.5748	0.064*
C10	0.5729 (2)	0.18140 (19)	0.56714 (16)	0.0649 (6)
H10A	0.6546	0.1667	0.6133	0.097*
H10B	0.5324	0.1187	0.5406	0.097*
H10C	0.5045	0.2175	0.6004	0.097*
C11	0.65494 (15)	0.11940 (12)	0.35916 (11)	0.0353 (3)
C12	0.53468 (18)	0.14587 (15)	0.29742 (13)	0.0479 (4)
H12	0.4966	0.2109	0.3018	0.058*
C13	0.46994 (19)	0.0771 (2)	0.22916 (15)	0.0600 (6)
H13	0.3890	0.0958	0.1881	0.072*
C14	0.5258 (2)	−0.01856 (18)	0.22248 (15)	0.0601 (6)
H14	0.4822	−0.0649	0.1768	0.072*
C15	0.6455 (2)	−0.04689 (15)	0.28250 (14)	0.0511 (5)
H15	0.6830	−0.1120	0.2772	0.061*
C16	0.71063 (17)	0.02175 (12)	0.35126 (12)	0.0381 (4)
C17	0.9048 (2)	−0.09245 (13)	0.40456 (14)	0.0490 (4)
H17A	0.8388	−0.1491	0.4015	0.059*
H17B	0.9719	−0.1016	0.4633	0.059*
C18	0.9838 (2)	−0.09675 (14)	0.31489 (14)	0.0507 (5)
H18A	0.9151	−0.0983	0.2564	0.061*
H18B	1.0360	−0.1605	0.3168	0.061*
C19	1.0867 (2)	−0.01005 (13)	0.30337 (14)	0.0503 (4)
H19A	1.1248	0.0131	0.3688	0.060*
H19B	1.1650	−0.0367	0.2714	0.060*
C20	1.0258 (2)	0.08130 (14)	0.24472 (13)	0.0482 (4)
H20A	1.1022	0.1162	0.2172	0.058*
H20B	0.9604	0.0569	0.1897	0.058*
N1	0.61418 (14)	0.24377 (11)	0.48733 (10)	0.0425 (3)
O1	0.73653 (13)	0.37542 (9)	0.43567 (10)	0.0488 (3)
O2	0.82817 (12)	0.00023 (8)	0.41494 (8)	0.0418 (3)
O3	0.95377 (12)	0.15360 (8)	0.29970 (9)	0.0398 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0358 (8)	0.0314 (7)	0.0331 (7)	−0.0014 (6)	0.0058 (6)	0.0058 (6)
C2	0.0354 (8)	0.0427 (9)	0.0509 (10)	0.0030 (7)	0.0114 (7)	0.0064 (7)
C3	0.0323 (8)	0.0550 (11)	0.0620 (11)	−0.0054 (7)	0.0012 (8)	0.0121 (9)
C4	0.0467 (10)	0.0496 (10)	0.0527 (11)	−0.0123 (8)	−0.0067 (8)	−0.0007 (8)
C5	0.0433 (9)	0.0390 (9)	0.0431 (9)	−0.0012 (7)	0.0021 (7)	−0.0025 (7)
C6	0.0322 (7)	0.0319 (7)	0.0333 (7)	−0.0001 (6)	0.0042 (6)	0.0055 (6)
C7	0.0344 (8)	0.0326 (7)	0.0367 (8)	0.0047 (6)	0.0026 (6)	0.0009 (6)
C8	0.0291 (7)	0.0375 (8)	0.0318 (7)	0.0037 (6)	0.0042 (6)	0.0007 (6)
C9	0.0487 (10)	0.0550 (11)	0.0568 (11)	0.0091 (8)	0.0124 (8)	−0.0136 (9)
C10	0.0673 (13)	0.0814 (15)	0.0513 (12)	0.0039 (11)	0.0287 (10)	0.0040 (10)
C11	0.0303 (7)	0.0439 (8)	0.0325 (8)	−0.0055 (6)	0.0071 (6)	0.0007 (6)
C12	0.0339 (8)	0.0651 (12)	0.0442 (9)	−0.0007 (8)	0.0023 (7)	−0.0005 (8)
C13	0.0363 (9)	0.0961 (17)	0.0455 (10)	−0.0113 (10)	−0.0039 (8)	−0.0031 (10)
C14	0.0527 (11)	0.0779 (15)	0.0492 (11)	−0.0288 (10)	0.0047 (9)	−0.0154 (10)
C15	0.0552 (11)	0.0491 (10)	0.0496 (10)	−0.0175 (8)	0.0088 (8)	−0.0093 (8)
C16	0.0405 (8)	0.0405 (8)	0.0340 (8)	−0.0097 (6)	0.0078 (6)	0.0005 (6)
C17	0.0680 (12)	0.0342 (9)	0.0441 (9)	0.0083 (8)	0.0040 (8)	0.0021 (7)
C18	0.0648 (12)	0.0383 (9)	0.0485 (10)	0.0084 (8)	0.0043 (9)	−0.0104 (7)
C19	0.0559 (11)	0.0435 (10)	0.0518 (10)	0.0095 (8)	0.0071 (8)	−0.0102 (8)
C20	0.0598 (11)	0.0477 (10)	0.0387 (9)	0.0055 (8)	0.0124 (8)	−0.0061 (7)
N1	0.0366 (7)	0.0511 (8)	0.0415 (8)	0.0051 (6)	0.0124 (6)	−0.0044 (6)
O1	0.0459 (7)	0.0345 (6)	0.0667 (8)	0.0107 (5)	0.0093 (6)	−0.0020 (5)
O2	0.0524 (7)	0.0364 (6)	0.0357 (6)	0.0058 (5)	0.0010 (5)	−0.0028 (5)
O3	0.0401 (6)	0.0356 (6)	0.0442 (6)	0.0002 (4)	0.0069 (5)	−0.0042 (5)

Geometric parameters (Å, º) top

C1—O3	1.3610 (19)	C10—H10C	0.9600
C1—C2	1.385 (2)	C11—C12	1.382 (2)
C1—C6	1.394 (2)	C11—C16	1.394 (2)
C2—C3	1.380 (3)	C12—C13	1.385 (3)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.369 (3)	C13—C14	1.368 (3)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.385 (2)	C14—C15	1.373 (3)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.383 (2)	C15—C16	1.390 (2)
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.513 (2)	C16—O2	1.362 (2)
C7—O1	1.4281 (18)	C17—O2	1.432 (2)
C7—C8	1.550 (2)	C17—C18	1.507 (3)
C7—H7	0.9800	C17—H17A	0.9700
C8—N1	1.4694 (19)	C17—H17B	0.9700
C8—C11	1.509 (2)	C18—C19	1.520 (3)
C8—H8	0.9800	C18—H18A	0.9700
C9—O1	1.406 (2)	C18—H18B	0.9700
C9—N1	1.432 (2)	C19—C20	1.515 (3)
C9—H9A	0.9700	C19—H19A	0.9700
C9—H9B	0.9700	C19—H19B	0.9700
C10—N1	1.449 (2)	C20—O3	1.430 (2)
C10—H10A	0.9600	C20—H20A	0.9700
C10—H10B	0.9600	C20—H20B	0.9700

O3—C1—C2	125.02 (14)	C11—C12—C13	121.06 (19)
O3—C1—C6	114.61 (13)	C11—C12—H12	119.5
C2—C1—C6	120.33 (14)	C13—C12—H12	119.5
C3—C2—C1	119.99 (16)	C14—C13—C12	119.61 (18)
C3—C2—H2	120.0	C14—C13—H13	120.2
C1—C2—H2	120.0	C12—C13—H13	120.2
C4—C3—C2	120.49 (16)	C13—C14—C15	120.65 (18)
C4—C3—H3	119.8	C13—C14—H14	119.7
C2—C3—H3	119.8	C15—C14—H14	119.7
C3—C4—C5	119.45 (16)	C14—C15—C16	119.94 (19)
C3—C4—H4	120.3	C14—C15—H15	120.0
C5—C4—H4	120.3	C16—C15—H15	120.0
C6—C5—C4	121.39 (16)	O2—C16—C15	124.24 (16)
C6—C5—H5	119.3	O2—C16—C11	115.64 (13)
C4—C5—H5	119.3	C15—C16—C11	120.12 (16)
C5—C6—C1	118.35 (14)	O2—C17—C18	114.82 (14)
C5—C6—C7	121.23 (14)	O2—C17—H17A	108.6
C1—C6—C7	120.36 (13)	C18—C17—H17A	108.6
O1—C7—C6	110.43 (12)	O2—C17—H17B	108.6
O1—C7—C8	105.22 (12)	C18—C17—H17B	108.6
C6—C7—C8	114.96 (12)	H17A—C17—H17B	107.5
O1—C7—H7	108.7	C17—C18—C19	116.37 (15)
C6—C7—H7	108.7	C17—C18—H18A	108.2
C8—C7—H7	108.7	C19—C18—H18A	108.2
N1—C8—C11	110.64 (12)	C17—C18—H18B	108.2
N1—C8—C7	101.88 (12)	C19—C18—H18B	108.2
C11—C8—C7	115.52 (12)	H18A—C18—H18B	107.3
N1—C8—H8	109.5	C20—C19—C18	115.66 (16)
C11—C8—H8	109.5	C20—C19—H19A	108.4
C7—C8—H8	109.5	C18—C19—H19A	108.4
O1—C9—N1	104.16 (14)	C20—C19—H19B	108.4
O1—C9—H9A	110.9	C18—C19—H19B	108.4
N1—C9—H9A	110.9	H19A—C19—H19B	107.4
O1—C9—H9B	110.9	O3—C20—C19	115.15 (14)
N1—C9—H9B	110.9	O3—C20—H20A	108.5
H9A—C9—H9B	108.9	C19—C20—H20A	108.5
N1—C10—H10A	109.5	O3—C20—H20B	108.5
N1—C10—H10B	109.5	C19—C20—H20B	108.5
H10A—C10—H10B	109.5	H20A—C20—H20B	107.5
N1—C10—H10C	109.5	C9—N1—C10	114.09 (16)
H10A—C10—H10C	109.5	C9—N1—C8	103.75 (13)
H10B—C10—H10C	109.5	C10—N1—C8	112.89 (15)
C12—C11—C16	118.61 (15)	C9—O1—C7	106.60 (12)
C12—C11—C8	120.11 (15)	C16—O2—C17	120.20 (13)
C16—C11—C8	121.28 (14)	C1—O3—C20	118.54 (13)

O3—C1—C2—C3	176.77 (15)	C12—C13—C14—C15	−0.2 (3)
C6—C1—C2—C3	−0.9 (2)	C13—C14—C15—C16	0.4 (3)
C1—C2—C3—C4	0.4 (3)	C14—C15—C16—O2	178.93 (16)
C2—C3—C4—C5	0.4 (3)	C14—C15—C16—C11	−0.2 (3)
C3—C4—C5—C6	−0.7 (3)	C12—C11—C16—O2	−179.29 (14)
C4—C5—C6—C1	0.2 (2)	C8—C11—C16—O2	−0.2 (2)
C4—C5—C6—C7	−176.75 (15)	C12—C11—C16—C15	−0.1 (2)
O3—C1—C6—C5	−177.30 (13)	C8—C11—C16—C15	179.04 (15)
C2—C1—C6—C5	0.6 (2)	O2—C17—C18—C19	54.9 (2)
O3—C1—C6—C7	−0.3 (2)	C17—C18—C19—C20	−90.5 (2)
C2—C1—C6—C7	177.57 (14)	C18—C19—C20—O3	83.15 (19)
C5—C6—C7—O1	5.6 (2)	O1—C9—N1—C10	167.06 (15)
C1—C6—C7—O1	−171.33 (13)	O1—C9—N1—C8	43.82 (17)
C5—C6—C7—C8	−113.29 (16)	C11—C8—N1—C9	−154.70 (14)
C1—C6—C7—C8	69.83 (18)	C7—C8—N1—C9	−31.35 (16)
O1—C7—C8—N1	8.90 (15)	C11—C8—N1—C10	81.28 (18)
C6—C7—C8—N1	130.61 (13)	C7—C8—N1—C10	−155.38 (15)
O1—C7—C8—C11	128.87 (13)	N1—C9—O1—C7	−38.20 (17)
C6—C7—C8—C11	−109.42 (15)	C6—C7—O1—C9	−107.21 (15)
N1—C8—C11—C12	45.81 (19)	C8—C7—O1—C9	17.41 (16)
C7—C8—C11—C12	−69.25 (18)	C15—C16—O2—C17	9.1 (2)
N1—C8—C11—C16	−133.28 (15)	C11—C16—O2—C17	−171.70 (14)
C7—C8—C11—C16	111.66 (15)	C18—C17—O2—C16	70.1 (2)
C16—C11—C12—C13	0.2 (2)	C2—C1—O3—C20	0.2 (2)
C8—C11—C12—C13	−178.90 (16)	C6—C1—O3—C20	177.96 (13)
C11—C12—C13—C14	−0.1 (3)	C19—C20—O3—C1	77.49 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1	0.93	2.37	2.735 (2)	103
C8—H8···O2	0.98	2.32	2.767 (2)	107
C14—H14···O1ⁱ	0.93	2.56	3.396 (2)	150

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₃NO₃
M_r	325.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.5193 (7), 13.0996 (8), 13.6000 (9)
β (°)	96.704 (3)
V (Å³)	1684.3 (2)
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 area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	33618, 3864, 2937
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.146, 1.02
No. of reflections	3864
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.19

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), 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
C5—H5···O1	0.93	2.37	2.735 (2)	103
C8—H8···O2	0.98	2.32	2.767 (2)	107
C14—H14···O1ⁱ	0.93	2.56	3.396 (2)	150

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Acknowledgements

BB thanks Dr Babu Varghese, SAIF, IIT-Madras, India, for his help with the data collection.

References

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