Methyl 3-(4-isopropyl­phen­yl)-1-phenyl-3,3a,4,9b-tetra­hydro-1H-chromeno[4,3-c]isoxazole-3a-carboxyl­ate

Kanchanadevi, J.; Anbalagan, G.; Srinivasan, J.; Bakthadoss, M.; Manivannan, V.

doi:10.1107/S1600536811026365

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1989

doi:10.1107/S1600536811026365

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Methyl 3-(4-isopropylphenyl)-1-phenyl-3,3a,4,9b-tetrahydro-1H-chromeno[4,3-c]isoxazole-3a-carboxylate

J. Kanchanadevi,^a G. Anbalagan,^b J. Srinivasan,^c M. Bakthadoss ^c and V. Manivannan ^d ^*

^aDepartment of Physics, Velammal Institute of Technology, Panchetty, Chennai 601 204, India, ^bDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, ^cDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India, and ^dDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
^*Correspondence e-mail: crystallography2010@gmail.com

(Received 23 June 2011; accepted 3 July 2011; online 9 July 2011)

In the title compound, C₂₇H₂₇NO₄, the five-membered isoxazole ring adopts an envelope conformation and the six-membered pyran ring adopts a half-chair conformation. The dihedral angle between the mean planes of the isoxazole ring and the chromene ring system is 54.95 (4)°.

Related literature

For the biological activity of chromenopyrrole, see: Caine (1993 ) and of benzopyran and isoxazolidine, see: Lin et al. (1996 ); Hu et al. (2004 ). For related structures, see: Gangadharan et al. (2011 ); Swaminathan et al. (2011 ).

Experimental

Crystal data

C₂₇H₂₇NO₄
M_r = 429.50
Triclinic, $[P \overline 1]$
a = 9.3555 (3) Å
b = 10.7247 (4) Å
c = 12.0449 (4) Å
α = 94.707 (1)°
β = 104.730 (1)°
γ = 96.385 (1)°
V = 1153.88 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 K
0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.937, T_max = 0.954
32129 measured reflections
8565 independent reflections
4738 reflections with I=2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.166
S = 1.03
8565 reflections
292 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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.

Supporting information

Crystal structure: contains datablock global. DOI: 10.1107/S1600536811026365/pv2423sup1.cif

checkCIF report

Comment top

Chromenopyrrole compounds are used in the treatment of impulsive disorders (Caine, 1993). It is well known that benzopyran and isoxazolidine derivatives possess interesting biological and pharmacological activities (Lin et al., 1996; Hu et al., 2004).

The geometric parameters of the title molecule (Fig. 1) agree well with the corresponding geometric parameters reported in closely related structures (Gangadharan et al., 2011; Swaminathan et al., 2011). The dihedral angle between the two benzene rings [(C11—C16) and (C17—C22)] is 73.02 (2) °. The sum of bond angles around N1 [335.04 (9) °]indicates the sp³ hybridization state of atom N1 in the molecule. The molecular structure is stabilized by weak intramolecular C—H···O interactions.

Related literature top

For the biological activity of chromenopyrrole, see: Caine et al. (1993) and of benzopyran and isoxazolidine, see: Lin et al. (1996); Hu et al. (2004). For related structures, see: Gangadharan et al. (2011); Swaminathan et al. (2011).

Experimental top

A mixture of (E)-methyl 2-((2-formylphenoxy)methyl)-3-(4-isopropylphenyl) acrylate (2 mmol, 0.68 g) and N-phenylhydroxylamine (3 mmol, 0.33 g) in ethanol (10 ml) was refluxed for 6 h. After the completion of the reaction as indicated by TLC, the reaction mixture was concentrated and the resulting crude mass was diluted with water (15 ml) and extracted with ethyl acetate (3x15 ml). The combined organic layer was washed with brine (3x15 ml) and dried over anhydrous Na₂SO₄, solvent was removed under reduced pressure. The crude mass was purified by column chromatography on silica gel (Acme 100–200 mesh), using ethyl acetate-hexane (0.5: 9.5) to afford the title compound as a colourless solid in 84% yield. The compound was recrystallised from ethyl acetate to produce X-ray diffraction quality crystals.

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).

Figures top

Fig. 1. The molecular structure of the title compound with atom labels and 30% probability displacement ellipsoids for non-H atoms.

Methyl 3-(4-isopropylphenyl)-1-phenyl-3,3a,4,9b-tetrahydro- 1H-chromeno[4,3-c]isoxazole-3a-carboxylate top

Crystal data top

C₂₇H₂₇NO₄	Z = 2
M_r = 429.50	F(000) = 456
Triclinic, P1	D_x = 1.236 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3555 (3) Å	Cell parameters from 8942 reflections
b = 10.7247 (4) Å	θ = 2.3–27.5°
c = 12.0449 (4) Å	µ = 0.08 mm⁻¹
α = 94.707 (1)°	T = 295 K
β = 104.730 (1)°	Block, colourless
γ = 96.385 (1)°	0.35 × 0.30 × 0.25 mm
V = 1153.88 (7) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	8565 independent reflections
Radiation source: fine-focus sealed tube	4738 reflections with I=2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 0 pixels mm^-1	θ_max = 33.0°, θ_min = 2.3°
ω and ϕ scans	h = −14→14
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −16→16
T_min = 0.937, T_max = 0.954	l = −18→17
32129 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.166	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0735P)² + 0.1032P] where P = (F_o² + 2F_c²)/3
8565 reflections	(Δ/σ)_max = 0.001
292 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₇H₂₇NO₄	γ = 96.385 (1)°
M_r = 429.50	V = 1153.88 (7) Å³
Triclinic, P1	Z = 2
a = 9.3555 (3) Å	Mo Kα radiation
b = 10.7247 (4) Å	µ = 0.08 mm⁻¹
c = 12.0449 (4) Å	T = 295 K
α = 94.707 (1)°	0.35 × 0.30 × 0.25 mm
β = 104.730 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	8565 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4738 reflections with I=2σ(I)
T_min = 0.937, T_max = 0.954	R_int = 0.030
32129 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.166	H-atom parameters constrained
S = 1.03	Δρ_max = 0.21 e Å⁻³
8565 reflections	Δρ_min = −0.23 e Å⁻³
292 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.60704 (18)	0.16741 (14)	0.53375 (12)	0.0569 (3)
H1	0.5311	0.2173	0.5296	0.068*
C2	0.6510 (2)	0.13476 (16)	0.43502 (13)	0.0680 (4)
H2	0.6063	0.1639	0.3656	0.082*
C3	0.7615 (2)	0.05886 (15)	0.44040 (14)	0.0676 (4)
H3	0.7895	0.0350	0.3738	0.081*
C4	0.83058 (18)	0.01821 (14)	0.54304 (14)	0.0614 (4)
H4	0.9048	−0.0333	0.5461	0.074*
C5	0.78884 (15)	0.05468 (12)	0.64292 (12)	0.0487 (3)
C6	0.87307 (13)	0.10646 (12)	0.84153 (11)	0.0460 (3)
H6A	0.9191	0.1884	0.8303	0.055*
H6B	0.9345	0.0801	0.9110	0.055*
C7	0.71742 (12)	0.11725 (10)	0.85621 (10)	0.0375 (2)
C8	0.61543 (13)	0.15211 (10)	0.74339 (10)	0.0389 (2)
H8	0.5169	0.1021	0.7291	0.047*
C9	0.67386 (14)	0.12726 (11)	0.63853 (10)	0.0439 (3)
C10	0.71737 (13)	0.23270 (10)	0.94285 (10)	0.0395 (2)
H10	0.6250	0.2215	0.9674	0.047*
C11	0.45688 (14)	0.31910 (11)	0.77135 (10)	0.0430 (3)
C12	0.32924 (15)	0.25929 (14)	0.69002 (12)	0.0537 (3)
H12	0.3366	0.1947	0.6362	0.064*
C13	0.19070 (17)	0.29527 (17)	0.68844 (14)	0.0670 (4)
H13	0.1060	0.2542	0.6338	0.080*
C14	0.1775 (2)	0.39055 (19)	0.76652 (15)	0.0755 (5)
H14	0.0845	0.4138	0.7659	0.091*
C15	0.3036 (2)	0.45114 (18)	0.84575 (15)	0.0786 (5)
H15	0.2955	0.5166	0.8985	0.094*
C16	0.44312 (18)	0.41693 (14)	0.84892 (13)	0.0611 (4)
H16	0.5274	0.4596	0.9030	0.073*
C17	0.84729 (13)	0.26602 (11)	1.04857 (11)	0.0421 (3)
C18	0.97498 (14)	0.34429 (12)	1.04776 (12)	0.0487 (3)
H18	0.9834	0.3755	0.9796	0.058*
C19	1.09029 (15)	0.37650 (13)	1.14762 (13)	0.0552 (3)
H19	1.1746	0.4302	1.1455	0.066*
C20	1.08295 (16)	0.33070 (13)	1.25029 (13)	0.0587 (4)
C21	0.95492 (18)	0.25349 (16)	1.25008 (14)	0.0690 (4)
H21	0.9470	0.2217	1.3181	0.083*
C22	0.83775 (16)	0.22189 (14)	1.15152 (12)	0.0588 (4)
H22	0.7521	0.1707	1.1545	0.071*
C23	1.2070 (2)	0.36685 (18)	1.36204 (16)	0.0839 (6)
H23	1.1953	0.3028	1.4138	0.101*
C24	1.3610 (2)	0.3669 (3)	1.3421 (2)	0.1332 (10)
H24A	1.3655	0.2878	1.3005	0.200*
H24B	1.4349	0.3785	1.4151	0.200*
H24C	1.3798	0.4345	1.2979	0.200*
C25	1.1916 (3)	0.4915 (3)	1.4210 (2)	0.1299 (10)
H25A	1.2074	0.5571	1.3740	0.195*
H25B	1.2643	0.5086	1.4946	0.195*
H25C	1.0933	0.4887	1.4321	0.195*
C26	0.64937 (13)	−0.00295 (11)	0.89318 (10)	0.0404 (3)
C27	0.6998 (2)	−0.16605 (17)	1.01174 (18)	0.0825 (6)
H27A	0.6501	−0.1412	1.0689	0.124*
H27B	0.7834	−0.2070	1.0468	0.124*
H27C	0.6315	−0.2233	0.9510	0.124*
N1	0.59985 (11)	0.28810 (9)	0.76661 (9)	0.0423 (2)
O1	0.86540 (10)	0.01709 (9)	0.74473 (9)	0.0559 (2)
O2	0.71185 (9)	0.33448 (8)	0.87192 (8)	0.0470 (2)
O3	0.75166 (11)	−0.05530 (10)	0.96424 (10)	0.0651 (3)
O4	0.51902 (11)	−0.04183 (10)	0.86632 (9)	0.0648 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0691 (9)	0.0559 (8)	0.0467 (7)	0.0098 (7)	0.0167 (6)	0.0054 (6)
C2	0.0911 (12)	0.0681 (10)	0.0451 (7)	0.0029 (9)	0.0221 (7)	0.0055 (7)
C3	0.0884 (11)	0.0617 (9)	0.0595 (9)	−0.0048 (8)	0.0418 (8)	−0.0040 (7)
C4	0.0672 (9)	0.0558 (8)	0.0708 (10)	0.0050 (7)	0.0401 (8)	−0.0014 (7)
C5	0.0512 (7)	0.0446 (7)	0.0552 (7)	0.0037 (5)	0.0250 (6)	0.0035 (5)
C6	0.0371 (6)	0.0510 (7)	0.0523 (7)	0.0081 (5)	0.0145 (5)	0.0092 (5)
C7	0.0348 (5)	0.0371 (5)	0.0421 (6)	0.0062 (4)	0.0121 (4)	0.0057 (4)
C8	0.0386 (5)	0.0354 (5)	0.0438 (6)	0.0066 (4)	0.0123 (5)	0.0049 (4)
C9	0.0498 (7)	0.0398 (6)	0.0435 (6)	0.0036 (5)	0.0169 (5)	0.0025 (5)
C10	0.0362 (5)	0.0372 (6)	0.0443 (6)	0.0033 (4)	0.0099 (5)	0.0053 (5)
C11	0.0502 (7)	0.0420 (6)	0.0387 (6)	0.0168 (5)	0.0095 (5)	0.0088 (5)
C12	0.0521 (7)	0.0584 (8)	0.0479 (7)	0.0177 (6)	0.0057 (6)	0.0019 (6)
C13	0.0533 (8)	0.0830 (11)	0.0625 (9)	0.0245 (8)	0.0038 (7)	0.0109 (8)
C14	0.0684 (10)	0.0972 (13)	0.0708 (10)	0.0476 (10)	0.0190 (8)	0.0172 (9)
C15	0.0887 (12)	0.0819 (11)	0.0700 (10)	0.0486 (10)	0.0180 (9)	−0.0039 (9)
C16	0.0691 (9)	0.0578 (8)	0.0535 (8)	0.0260 (7)	0.0070 (7)	−0.0044 (6)
C17	0.0391 (6)	0.0373 (6)	0.0470 (6)	0.0030 (5)	0.0071 (5)	0.0037 (5)
C18	0.0443 (6)	0.0479 (7)	0.0510 (7)	−0.0009 (5)	0.0094 (5)	0.0095 (5)
C19	0.0431 (7)	0.0484 (7)	0.0655 (9)	−0.0052 (5)	0.0028 (6)	0.0107 (6)
C20	0.0564 (8)	0.0504 (8)	0.0573 (8)	−0.0019 (6)	−0.0054 (6)	0.0135 (6)
C21	0.0689 (10)	0.0738 (10)	0.0526 (8)	−0.0130 (8)	−0.0008 (7)	0.0245 (7)
C22	0.0522 (7)	0.0617 (8)	0.0551 (8)	−0.0108 (6)	0.0064 (6)	0.0146 (6)
C23	0.0793 (12)	0.0758 (11)	0.0705 (11)	−0.0177 (9)	−0.0212 (9)	0.0270 (9)
C24	0.0680 (13)	0.171 (3)	0.129 (2)	0.0246 (15)	−0.0369 (13)	0.0206 (19)
C25	0.1180 (19)	0.143 (2)	0.0866 (15)	−0.0023 (17)	−0.0268 (14)	−0.0302 (15)
C26	0.0416 (6)	0.0378 (6)	0.0444 (6)	0.0072 (5)	0.0154 (5)	0.0044 (5)
C27	0.0738 (11)	0.0735 (11)	0.1208 (16)	0.0249 (9)	0.0416 (11)	0.0604 (11)
N1	0.0438 (5)	0.0388 (5)	0.0418 (5)	0.0082 (4)	0.0063 (4)	0.0032 (4)
O1	0.0552 (5)	0.0592 (6)	0.0633 (6)	0.0236 (4)	0.0262 (5)	0.0091 (5)
O2	0.0469 (5)	0.0359 (4)	0.0518 (5)	0.0033 (3)	0.0024 (4)	0.0053 (4)
O3	0.0478 (5)	0.0641 (6)	0.0934 (8)	0.0159 (4)	0.0223 (5)	0.0444 (6)
O4	0.0472 (5)	0.0686 (6)	0.0718 (7)	−0.0101 (5)	0.0062 (5)	0.0244 (5)

Geometric parameters (Å, º) top

C1—C9	1.3846 (19)	C14—H14	0.9300
C1—C2	1.385 (2)	C15—C16	1.386 (2)
C1—H1	0.9300	C15—H15	0.9300
C2—C3	1.377 (2)	C16—H16	0.9300
C2—H2	0.9300	C17—C22	1.3831 (19)
C3—C4	1.371 (2)	C17—C18	1.3841 (17)
C3—H3	0.9300	C18—C19	1.3853 (18)
C4—C5	1.3959 (18)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.382 (2)
C5—O1	1.3703 (17)	C19—H19	0.9300
C5—C9	1.3893 (18)	C20—C21	1.378 (2)
C6—O1	1.4289 (16)	C20—C23	1.526 (2)
C6—C7	1.5265 (16)	C21—C22	1.3840 (19)
C6—H6A	0.9700	C21—H21	0.9300
C6—H6B	0.9700	C22—H22	0.9300
C7—C26	1.5235 (16)	C23—C25	1.501 (3)
C7—C8	1.5492 (16)	C23—C24	1.520 (3)
C7—C10	1.5525 (16)	C23—H23	0.9800
C8—N1	1.4925 (15)	C24—H24A	0.9600
C8—C9	1.5144 (16)	C24—H24B	0.9600
C8—H8	0.9800	C24—H24C	0.9600
C10—O2	1.4378 (14)	C25—H25A	0.9600
C10—C17	1.5060 (16)	C25—H25B	0.9600
C10—H10	0.9800	C25—H25C	0.9600
C11—C16	1.3858 (18)	C26—O4	1.1957 (14)
C11—C12	1.3887 (18)	C26—O3	1.3211 (15)
C11—N1	1.4274 (16)	C27—O3	1.4484 (17)
C12—C13	1.389 (2)	C27—H27A	0.9600
C12—H12	0.9300	C27—H27B	0.9600
C13—C14	1.369 (2)	C27—H27C	0.9600
C13—H13	0.9300	N1—O2	1.4350 (13)
C14—C15	1.371 (3)

C9—C1—C2	121.34 (14)	C16—C15—H15	119.3
C9—C1—H1	119.3	C11—C16—C15	119.93 (15)
C2—C1—H1	119.3	C11—C16—H16	120.0
C3—C2—C1	119.49 (15)	C15—C16—H16	120.0
C3—C2—H2	120.3	C22—C17—C18	118.30 (12)
C1—C2—H2	120.3	C22—C17—C10	119.56 (11)
C4—C3—C2	120.59 (14)	C18—C17—C10	122.09 (11)
C4—C3—H3	119.7	C17—C18—C19	120.57 (12)
C2—C3—H3	119.7	C17—C18—H18	119.7
C3—C4—C5	119.60 (14)	C19—C18—H18	119.7
C3—C4—H4	120.2	C20—C19—C18	121.50 (13)
C5—C4—H4	120.2	C20—C19—H19	119.3
O1—C5—C9	121.49 (11)	C18—C19—H19	119.3
O1—C5—C4	117.81 (12)	C21—C20—C19	117.34 (13)
C9—C5—C4	120.70 (13)	C21—C20—C23	120.08 (14)
O1—C6—C7	110.68 (10)	C19—C20—C23	122.53 (14)
O1—C6—H6A	109.5	C20—C21—C22	121.90 (14)
C7—C6—H6A	109.5	C20—C21—H21	119.0
O1—C6—H6B	109.5	C22—C21—H21	119.0
C7—C6—H6B	109.5	C17—C22—C21	120.37 (13)
H6A—C6—H6B	108.1	C17—C22—H22	119.8
C26—C7—C6	111.81 (9)	C21—C22—H22	119.8
C26—C7—C8	111.35 (9)	C25—C23—C24	111.4 (2)
C6—C7—C8	110.09 (9)	C25—C23—C20	110.72 (16)
C26—C7—C10	110.01 (9)	C24—C23—C20	112.07 (18)
C6—C7—C10	111.99 (9)	C25—C23—H23	107.5
C8—C7—C10	101.13 (8)	C24—C23—H23	107.5
N1—C8—C9	111.90 (9)	C20—C23—H23	107.5
N1—C8—C7	105.99 (9)	C23—C24—H24A	109.5
C9—C8—C7	113.50 (9)	C23—C24—H24B	109.5
N1—C8—H8	108.4	H24A—C24—H24B	109.5
C9—C8—H8	108.4	C23—C24—H24C	109.5
C7—C8—H8	108.4	H24A—C24—H24C	109.5
C1—C9—C5	118.20 (12)	H24B—C24—H24C	109.5
C1—C9—C8	121.15 (11)	C23—C25—H25A	109.5
C5—C9—C8	120.46 (11)	C23—C25—H25B	109.5
O2—C10—C17	109.26 (9)	H25A—C25—H25B	109.5
O2—C10—C7	102.26 (9)	C23—C25—H25C	109.5
C17—C10—C7	118.65 (9)	H25A—C25—H25C	109.5
O2—C10—H10	108.7	H25B—C25—H25C	109.5
C17—C10—H10	108.7	O4—C26—O3	123.99 (11)
C7—C10—H10	108.7	O4—C26—C7	124.51 (11)
C16—C11—C12	118.53 (12)	O3—C26—C7	111.39 (10)
C16—C11—N1	121.18 (12)	O3—C27—H27A	109.5
C12—C11—N1	119.98 (11)	O3—C27—H27B	109.5
C11—C12—C13	120.50 (13)	H27A—C27—H27B	109.5
C11—C12—H12	119.7	O3—C27—H27C	109.5
C13—C12—H12	119.7	H27A—C27—H27C	109.5
C14—C13—C12	120.70 (15)	H27B—C27—H27C	109.5
C14—C13—H13	119.7	C11—N1—O2	111.46 (9)
C12—C13—H13	119.7	C11—N1—C8	118.02 (10)
C13—C14—C15	118.93 (15)	O2—N1—C8	105.56 (8)
C13—C14—H14	120.5	C5—O1—C6	111.86 (9)
C15—C14—H14	120.5	N1—O2—C10	105.57 (8)
C14—C15—C16	121.40 (15)	C26—O3—C27	116.86 (11)
C14—C15—H15	119.3

C9—C1—C2—C3	1.2 (2)	O2—C10—C17—C18	−29.12 (15)
C1—C2—C3—C4	−1.7 (2)	C7—C10—C17—C18	87.45 (14)
C2—C3—C4—C5	−0.3 (2)	C22—C17—C18—C19	0.4 (2)
C3—C4—C5—O1	−176.94 (13)	C10—C17—C18—C19	177.75 (12)
C3—C4—C5—C9	2.7 (2)	C17—C18—C19—C20	0.9 (2)
O1—C6—C7—C26	68.26 (13)	C18—C19—C20—C21	−1.2 (2)
O1—C6—C7—C8	−56.07 (13)	C18—C19—C20—C23	−178.72 (15)
O1—C6—C7—C10	−167.75 (9)	C19—C20—C21—C22	0.3 (3)
C26—C7—C8—N1	130.21 (10)	C23—C20—C21—C22	177.81 (16)
C6—C7—C8—N1	−105.20 (10)	C18—C17—C22—C21	−1.4 (2)
C10—C7—C8—N1	13.38 (11)	C10—C17—C22—C21	−178.79 (14)
C26—C7—C8—C9	−106.59 (11)	C20—C21—C22—C17	1.1 (3)
C6—C7—C8—C9	18.01 (13)	C21—C20—C23—C25	−94.8 (2)
C10—C7—C8—C9	136.58 (10)	C19—C20—C23—C25	82.6 (3)
C2—C1—C9—C5	1.1 (2)	C21—C20—C23—C24	140.1 (2)
C2—C1—C9—C8	−173.87 (13)	C19—C20—C23—C24	−42.5 (2)
O1—C5—C9—C1	176.55 (12)	C6—C7—C26—O4	−147.55 (13)
C4—C5—C9—C1	−3.1 (2)	C8—C7—C26—O4	−23.93 (16)
O1—C5—C9—C8	−8.42 (19)	C10—C7—C26—O4	87.35 (15)
C4—C5—C9—C8	171.93 (11)	C6—C7—C26—O3	36.03 (14)
N1—C8—C9—C1	−51.91 (15)	C8—C7—C26—O3	159.65 (10)
C7—C8—C9—C1	−171.81 (11)	C10—C7—C26—O3	−89.07 (12)
N1—C8—C9—C5	133.21 (12)	C16—C11—N1—O2	20.92 (16)
C7—C8—C9—C5	13.31 (16)	C12—C11—N1—O2	−165.45 (11)
C26—C7—C10—O2	−152.76 (9)	C16—C11—N1—C8	143.32 (13)
C6—C7—C10—O2	82.24 (11)	C12—C11—N1—C8	−43.05 (16)
C8—C7—C10—O2	−34.95 (10)	C9—C8—N1—C11	123.40 (11)
C26—C7—C10—C17	87.01 (12)	C7—C8—N1—C11	−112.39 (11)
C6—C7—C10—C17	−37.99 (14)	C9—C8—N1—O2	−111.26 (10)
C8—C7—C10—C17	−155.18 (10)	C7—C8—N1—O2	12.96 (11)
C16—C11—C12—C13	−1.4 (2)	C9—C5—O1—C6	−30.67 (16)
N1—C11—C12—C13	−175.17 (13)	C4—C5—O1—C6	148.99 (12)
C11—C12—C13—C14	0.3 (2)	C7—C6—O1—C5	63.65 (13)
C12—C13—C14—C15	0.7 (3)	C11—N1—O2—C10	92.31 (10)
C13—C14—C15—C16	−0.7 (3)	C8—N1—O2—C10	−37.00 (11)
C12—C11—C16—C15	1.4 (2)	C17—C10—O2—N1	171.97 (9)
N1—C11—C16—C15	175.13 (14)	C7—C10—O2—N1	45.40 (10)
C14—C15—C16—C11	−0.4 (3)	O4—C26—O3—C27	−0.3 (2)
O2—C10—C17—C22	148.15 (12)	C7—C26—O3—C27	176.14 (13)
C7—C10—C17—C22	−95.27 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6B···O3	0.97	2.37	2.706 (2)	100
C8—H8···O4	0.98	2.35	2.846 (2)	111
C16—H16···O2	0.93	2.38	2.713 (2)	101

Experimental details

Crystal data
Chemical formula	C₂₇H₂₇NO₄
M_r	429.50
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	9.3555 (3), 10.7247 (4), 12.0449 (4)
α, β, γ (°)	94.707 (1), 104.730 (1), 96.385 (1)
V (Å³)	1153.88 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.35 × 0.30 × 0.25

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.937, 0.954
No. of measured, independent and observed [I=2σ(I)] reflections	32129, 8565, 4738
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.766

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.166, 1.03
No. of reflections	8565
No. of parameters	292
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.23

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

References

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