Methyl 5-phenyl-1,2,3,4,4a,5,5a,13c-octahydro-6H-benzo[f]chromeno[3,4-b]indolizine-5a-carboxyl­ate

Kamala, E.T.S.; Nirmala, S.; Sudha, L.; Kathiravan, S.; Raghunathan, R.

doi:10.1107/S1600536809026774

Methyl 5-phenyl-1,2,3,4,4a,5,5a,13c-octahydro-6H-benzo[f]chromeno[3,4-b]indolizine-5a-carboxylate

E. T. S. Kamala, S. Nirmala, L. Sudha, S. Kathiravan and R. Raghunathan

In the title compound, C₂₇H₂₇NO₃, the pyrrolidine ring exhibits a twist conformation and the piperidine ring exhibits a chair conformation. The pyrrolidine ring makes dihedral angles of 54.47 (5), 51.50 (5) and 73.37 (6)° with the napthalene ring system and the tetrahydropyran and phenyl rings, respectively. The structure is stabilized by intramolecular C—H

O and C—H

N interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809026774/bt2988sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536809026774/bt2988Isup2.hkl Contains datablock I

CCDC reference: 744426

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R factor = 0.044
wR factor = 0.122
Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)         30 Ang.

Alert level G
PLAT066_ALERT_1_G Predicted and Reported Transmissions Identical .          ?
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal  (x 10000)        200 Deg.
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT793_ALERT_4_G The Model has Chirality at C5      (Verify) ....          S
PLAT793_ALERT_4_G The Model has Chirality at C6      (Verify) ....          S
PLAT793_ALERT_4_G The Model has Chirality at C7      (Verify) ....          S
PLAT793_ALERT_4_G The Model has Chirality at C8      (Verify) ....          S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   8 ALERT level G = General alerts; check

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Indolizines, the nitrogen containing heterocyclic systems, are widely distributed in nature; in particular, indolizine derivatives are an important class of heterocyclic bioactive compounds with a wide range of applications, such as pharmaceutical drugs, potential central nervous system depressants, calcium entry blockers, cardiovascular agents, spectral sensitizers and novel dyes(Gubin et al., 1992; Gupta et al., 2003; Poty et al., 1994; Hema et al., 2003).Moreover indolizine derivatives have been found to possess a variety of biological activities such as antiinflammatory (Malonne et al., 1998), antiviral (Medda et al., 2003).

Fig 1 shows the ORTEP plot of compound (I). Bond lengths and angles are comparable with other reported values.

In the molecule the pyrrolidine ring N1/C5/C6/C7/C8 exhibits twist conformation with assymetry parameters (Nardelli, 1983) ΔC_s(N1) =23.66 (1)/ (C8) = 14.95 (1) and with the puckering parameters (Cremer and Pople, 1975) q2 = 0.4749 (1)Å and ϕ2 = 155.74 (2)°. The six membered ring N1/C1—C5 exhibits chair conformation with assymetry parameters ΔC_s(N1) = 2.78 (1)/(C3) = 2.78 (1) and with the puckering parameters Q = 0.5788 (2) Å, Θ = 175.62 (2)° and ϕ = 145 (2)°. The sum of bond angles around N1 [331.99 (3)°] indicates sp³ hybridization. The pyrrolidine ring makes dihedral angles of 54.47 (5)°, 51.50 (5)° and 73.37 (6)° with the napthalene,tetrahydro pyran and phenyl rings respectively. The napthalene and tetrahydro pyran rings are almost planar with each other with a dihedral angle of 8.88 (4)°,

In the crystal packing, atom O3 is involved in intramolecular C - H···O interactions and atom N1 contributes to C - H···N intramolecular interactions.

Related literature top

For general background to the applications and biological activity of indolizine derivatives, see: Gubin et al. (1992); Gupta et al. (2003); Poty et al. (1994); Hema et al. (2003); Malonne et al. (1998); Medda et al. (2003). For puckering parameters, see: Cremer and Pople (1975). For asymmetry parameters, see: Nardelli (1983).

Experimental top

A mixture of (Z)-methyl 2-(1-formylnaphthalen-2-yloxy)-3-p-tolylacrylate and pipecolinic acid were refluxed in benzene for 20 h and the solvent was removed under reduced pressure. The crude product was subjected to column chromatography to get the pure product. The product was recrystallized from dry benzene by slow evaporation.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: APEX2 and 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: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids.
	Fig. 2. The packing of the molecules viewed along b axis.

Methyl 5-phenyl-1,2,3,4,4a,5,5a,13c-octahydro-6H- benzo[f]chromeno[3,4-b]indolizine-5a-carboxylate top

Crystal data top

C₂₇H₂₇NO₃	Z = 2
M_r = 413.50	F(000) = 440
Triclinic, P1	D_x = 1.288 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4201 (3) Å	Cell parameters from 22685 reflections
b = 10.6752 (3) Å	θ = 2.0–27.0°
c = 11.0761 (3) Å	µ = 0.08 mm⁻¹
α = 78.262 (2)°	T = 293 K
β = 77.911 (2)°	Needle, colourless
γ = 87.346 (2)°	0.30 × 0.20 × 0.15 mm
V = 1066.34 (5) Å³

Data collection top

Bruker Kappa APEXII diffractometer	4641 independent reflections
Radiation source: fine-focus sealed tube	3461 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω and ϕ scans	θ_max = 27.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→12
T_min = 0.975, T_max = 0.988	k = −13→13
22685 measured reflections	l = −14→14

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.122	w = 1/[σ²(F_o²) + (0.0534P)² + 0.3168P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
4641 reflections	Δρ_max = 0.34 e Å⁻³
281 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.012 (2)

Crystal data top

C₂₇H₂₇NO₃	γ = 87.346 (2)°
M_r = 413.50	V = 1066.34 (5) Å³
Triclinic, P1	Z = 2
a = 9.4201 (3) Å	Mo Kα radiation
b = 10.6752 (3) Å	µ = 0.08 mm⁻¹
c = 11.0761 (3) Å	T = 293 K
α = 78.262 (2)°	0.30 × 0.20 × 0.15 mm
β = 77.911 (2)°

Data collection top

Bruker Kappa APEXII diffractometer	4641 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3461 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.988	R_int = 0.026
22685 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.00	Δρ_max = 0.34 e Å⁻³
4641 reflections	Δρ_min = −0.23 e Å⁻³
281 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	0.54853 (15)	0.76212 (14)	0.13837 (13)	0.0396 (3)
H1A	0.4898	0.7171	0.2165	0.047*
H1B	0.5454	0.8527	0.1403	0.047*
C2	0.70388 (16)	0.71426 (15)	0.12642 (15)	0.0453 (4)
H2A	0.7052	0.6221	0.1343	0.054*
H2B	0.7439	0.7339	0.1943	0.054*
C3	0.79742 (17)	0.77508 (18)	0.00095 (16)	0.0540 (4)
H3A	0.8930	0.7357	−0.0077	0.065*
H3B	0.8089	0.8655	−0.0016	0.065*
C4	0.72958 (17)	0.75893 (18)	−0.10770 (16)	0.0504 (4)
H4A	0.7854	0.8056	−0.1864	0.060*
H4B	0.7295	0.6692	−0.1125	0.060*
C5	0.57534 (15)	0.80960 (13)	−0.08654 (13)	0.0366 (3)
H5	0.5812	0.8987	−0.0780	0.044*
C6	0.47933 (16)	0.80945 (13)	−0.18463 (13)	0.0378 (3)
H6	0.4643	0.8996	−0.2206	0.045*
C7	0.32917 (15)	0.76056 (13)	−0.10062 (13)	0.0365 (3)
C8	0.33931 (14)	0.78431 (12)	0.02922 (13)	0.0340 (3)
H8	0.3313	0.8762	0.0288	0.041*
C9	0.22386 (15)	0.71384 (13)	0.13304 (13)	0.0376 (3)
C10	0.17673 (15)	0.75355 (14)	0.25133 (14)	0.0412 (3)
C11	0.23444 (18)	0.86035 (16)	0.28129 (15)	0.0476 (4)
H11	0.3068	0.9082	0.2220	0.057*
C12	0.1870 (2)	0.8954 (2)	0.39497 (17)	0.0612 (5)
H12	0.2275	0.9661	0.4118	0.073*
C13	0.0784 (2)	0.8262 (2)	0.48593 (17)	0.0714 (6)
H13	0.0478	0.8495	0.5638	0.086*
C14	0.0178 (2)	0.7247 (2)	0.46007 (17)	0.0658 (5)
H14	−0.0558	0.6797	0.5205	0.079*
C15	0.06357 (17)	0.68546 (16)	0.34362 (15)	0.0501 (4)
C16	−0.00152 (18)	0.58123 (17)	0.31539 (17)	0.0572 (5)
H16	−0.0748	0.5357	0.3758	0.069*
C17	0.04018 (17)	0.54627 (16)	0.20290 (18)	0.0540 (4)
H17	−0.0050	0.4782	0.1857	0.065*
C18	0.15284 (16)	0.61359 (14)	0.11133 (15)	0.0431 (4)
C19	0.30894 (17)	0.61779 (14)	−0.08800 (15)	0.0441 (4)
H19A	0.3044	0.6000	−0.1696	0.053*
H19B	0.3921	0.5724	−0.0612	0.053*
C20	0.53277 (16)	0.74536 (14)	−0.29578 (14)	0.0413 (3)
C21	0.59051 (17)	0.62247 (15)	−0.28796 (15)	0.0478 (4)
H21	0.6021	0.5754	−0.2102	0.057*
C22	0.63086 (19)	0.56903 (18)	−0.39354 (18)	0.0571 (4)
H22	0.6691	0.4866	−0.3863	0.069*
C23	0.6149 (2)	0.6367 (2)	−0.50911 (18)	0.0688 (5)
H23	0.6415	0.6004	−0.5801	0.083*
C24	0.5594 (2)	0.7582 (2)	−0.51919 (17)	0.0750 (6)
H24	0.5486	0.8048	−0.5974	0.090*
C25	0.5192 (2)	0.81199 (18)	−0.41372 (15)	0.0589 (5)
H25	0.4823	0.8949	−0.4222	0.071*
C26	0.20768 (16)	0.83093 (14)	−0.15768 (14)	0.0420 (4)
C27	0.0803 (2)	1.02515 (18)	−0.1933 (2)	0.0728 (6)
H27A	0.0737	1.1075	−0.1703	0.109*
H27B	−0.0126	0.9839	−0.1656	0.109*
H27C	0.1093	1.0355	−0.2832	0.109*
N1	0.49017 (12)	0.74134 (10)	0.03267 (10)	0.0349 (3)
O1	0.17989 (12)	0.57199 (10)	0.00045 (11)	0.0524 (3)
O2	0.13962 (15)	0.78741 (13)	−0.21840 (14)	0.0738 (4)
O3	0.18643 (13)	0.94760 (11)	−0.13447 (13)	0.0610 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0406 (8)	0.0426 (8)	0.0360 (8)	0.0003 (6)	−0.0123 (6)	−0.0045 (6)
C2	0.0417 (8)	0.0485 (8)	0.0495 (9)	0.0022 (7)	−0.0186 (7)	−0.0092 (7)
C3	0.0359 (8)	0.0718 (11)	0.0571 (11)	−0.0019 (8)	−0.0116 (7)	−0.0172 (9)
C4	0.0384 (8)	0.0672 (10)	0.0466 (9)	−0.0003 (7)	−0.0068 (7)	−0.0153 (8)
C5	0.0401 (8)	0.0355 (7)	0.0331 (7)	−0.0035 (6)	−0.0068 (6)	−0.0042 (6)
C6	0.0427 (8)	0.0346 (7)	0.0344 (8)	0.0016 (6)	−0.0092 (6)	−0.0020 (6)
C7	0.0380 (7)	0.0355 (7)	0.0368 (8)	0.0032 (6)	−0.0112 (6)	−0.0062 (6)
C8	0.0354 (7)	0.0320 (6)	0.0348 (7)	0.0028 (5)	−0.0116 (6)	−0.0035 (5)
C9	0.0332 (7)	0.0377 (7)	0.0384 (8)	0.0052 (6)	−0.0093 (6)	0.0010 (6)
C10	0.0353 (7)	0.0467 (8)	0.0377 (8)	0.0105 (6)	−0.0105 (6)	0.0016 (6)
C11	0.0452 (9)	0.0583 (9)	0.0393 (8)	0.0089 (7)	−0.0116 (7)	−0.0083 (7)
C12	0.0594 (11)	0.0808 (13)	0.0485 (10)	0.0128 (9)	−0.0170 (9)	−0.0209 (9)
C13	0.0698 (13)	0.1044 (17)	0.0372 (10)	0.0179 (12)	−0.0085 (9)	−0.0145 (10)
C14	0.0548 (11)	0.0877 (14)	0.0406 (10)	0.0156 (10)	0.0001 (8)	0.0062 (9)
C15	0.0393 (8)	0.0583 (10)	0.0431 (9)	0.0113 (7)	−0.0065 (7)	0.0075 (7)
C16	0.0392 (9)	0.0582 (10)	0.0591 (11)	0.0025 (8)	0.0005 (8)	0.0119 (8)
C17	0.0380 (8)	0.0464 (9)	0.0707 (12)	−0.0031 (7)	−0.0078 (8)	0.0018 (8)
C18	0.0356 (7)	0.0408 (8)	0.0492 (9)	0.0031 (6)	−0.0088 (7)	−0.0013 (7)
C19	0.0437 (8)	0.0409 (8)	0.0480 (9)	−0.0014 (6)	−0.0076 (7)	−0.0113 (7)
C20	0.0406 (8)	0.0486 (8)	0.0342 (8)	−0.0004 (6)	−0.0088 (6)	−0.0058 (6)
C21	0.0476 (9)	0.0520 (9)	0.0443 (9)	0.0055 (7)	−0.0102 (7)	−0.0111 (7)
C22	0.0482 (9)	0.0654 (11)	0.0605 (11)	0.0050 (8)	−0.0059 (8)	−0.0255 (9)
C23	0.0632 (12)	0.0998 (16)	0.0486 (11)	0.0020 (11)	−0.0046 (9)	−0.0338 (11)
C24	0.0890 (15)	0.1004 (16)	0.0344 (10)	0.0088 (13)	−0.0153 (10)	−0.0098 (10)
C25	0.0689 (12)	0.0660 (11)	0.0385 (9)	0.0091 (9)	−0.0128 (8)	−0.0031 (8)
C26	0.0432 (8)	0.0482 (8)	0.0380 (8)	0.0029 (7)	−0.0154 (7)	−0.0098 (6)
C27	0.0742 (13)	0.0566 (11)	0.0990 (16)	0.0198 (9)	−0.0548 (12)	−0.0080 (10)
N1	0.0328 (6)	0.0373 (6)	0.0334 (6)	0.0007 (5)	−0.0090 (5)	−0.0022 (5)
O1	0.0482 (6)	0.0477 (6)	0.0609 (7)	−0.0112 (5)	−0.0050 (5)	−0.0140 (5)
O2	0.0823 (10)	0.0762 (9)	0.0850 (10)	0.0176 (7)	−0.0542 (8)	−0.0328 (8)
O3	0.0680 (8)	0.0456 (6)	0.0851 (9)	0.0183 (5)	−0.0509 (7)	−0.0167 (6)

Geometric parameters (Å, º) top

C1—N1	1.4521 (18)	C12—H12	0.9300
C1—C2	1.5157 (19)	C13—C14	1.355 (3)
C1—H1A	0.9700	C13—H13	0.9300
C1—H1B	0.9700	C14—C15	1.412 (3)
C2—C3	1.517 (2)	C14—H14	0.9300
C2—H2A	0.9700	C15—C16	1.413 (3)
C2—H2B	0.9700	C16—C17	1.348 (3)
C3—C4	1.518 (2)	C16—H16	0.9300
C3—H3A	0.9700	C17—C18	1.412 (2)
C3—H3B	0.9700	C17—H17	0.9300
C4—C5	1.515 (2)	C18—O1	1.3604 (19)
C4—H4A	0.9700	C19—O1	1.4276 (18)
C4—H4B	0.9700	C19—H19A	0.9700
C5—N1	1.4618 (17)	C19—H19B	0.9700
C5—C6	1.553 (2)	C20—C25	1.383 (2)
C5—H5	0.9800	C20—C21	1.390 (2)
C6—C20	1.5128 (19)	C21—C22	1.379 (2)
C6—C7	1.568 (2)	C21—H21	0.9300
C6—H6	0.9800	C22—C23	1.370 (3)
C7—C26	1.5178 (19)	C22—H22	0.9300
C7—C19	1.5191 (19)	C23—C24	1.368 (3)
C7—C8	1.5328 (19)	C23—H23	0.9300
C8—N1	1.4788 (16)	C24—C25	1.380 (3)
C8—C9	1.5070 (19)	C24—H24	0.9300
C8—H8	0.9800	C25—H25	0.9300
C9—C18	1.375 (2)	C26—O2	1.1892 (18)
C9—C10	1.435 (2)	C26—O3	1.3203 (18)
C10—C11	1.412 (2)	C27—O3	1.4445 (18)
C10—C15	1.422 (2)	C27—H27A	0.9600
C11—C12	1.366 (2)	C27—H27B	0.9600
C11—H11	0.9300	C27—H27C	0.9600
C12—C13	1.393 (3)

N1—C1—C2	110.04 (12)	C11—C12—H12	119.7
N1—C1—H1A	109.7	C13—C12—H12	119.7
C2—C1—H1A	109.7	C14—C13—C12	119.46 (18)
N1—C1—H1B	109.7	C14—C13—H13	120.3
C2—C1—H1B	109.7	C12—C13—H13	120.3
H1A—C1—H1B	108.2	C13—C14—C15	121.63 (18)
C1—C2—C3	111.46 (13)	C13—C14—H14	119.2
C1—C2—H2A	109.3	C15—C14—H14	119.2
C3—C2—H2A	109.3	C14—C15—C16	121.75 (17)
C1—C2—H2B	109.3	C14—C15—C10	119.33 (18)
C3—C2—H2B	109.3	C16—C15—C10	118.91 (15)
H2A—C2—H2B	108.0	C17—C16—C15	121.48 (16)
C2—C3—C4	110.99 (14)	C17—C16—H16	119.3
C2—C3—H3A	109.4	C15—C16—H16	119.3
C4—C3—H3A	109.4	C16—C17—C18	119.65 (17)
C2—C3—H3B	109.4	C16—C17—H17	120.2
C4—C3—H3B	109.4	C18—C17—H17	120.2
H3A—C3—H3B	108.0	O1—C18—C9	124.15 (14)
C5—C4—C3	108.85 (13)	O1—C18—C17	113.58 (14)
C5—C4—H4A	109.9	C9—C18—C17	122.24 (15)
C3—C4—H4A	109.9	O1—C19—C7	111.98 (12)
C5—C4—H4B	109.9	O1—C19—H19A	109.2
C3—C4—H4B	109.9	C7—C19—H19A	109.2
H4A—C4—H4B	108.3	O1—C19—H19B	109.2
N1—C5—C4	110.61 (12)	C7—C19—H19B	109.2
N1—C5—C6	104.91 (11)	H19A—C19—H19B	107.9
C4—C5—C6	120.75 (12)	C25—C20—C21	117.25 (15)
N1—C5—H5	106.6	C25—C20—C6	117.84 (14)
C4—C5—H5	106.6	C21—C20—C6	124.88 (13)
C6—C5—H5	106.6	C22—C21—C20	121.16 (16)
C20—C6—C5	120.22 (12)	C22—C21—H21	119.4
C20—C6—C7	115.04 (12)	C20—C21—H21	119.4
C5—C6—C7	103.10 (11)	C23—C22—C21	120.37 (17)
C20—C6—H6	105.8	C23—C22—H22	119.8
C5—C6—H6	105.8	C21—C22—H22	119.8
C7—C6—H6	105.8	C24—C23—C22	119.46 (17)
C26—C7—C19	108.51 (12)	C24—C23—H23	120.3
C26—C7—C8	115.68 (11)	C22—C23—H23	120.3
C19—C7—C8	107.65 (11)	C23—C24—C25	120.25 (18)
C26—C7—C6	109.40 (11)	C23—C24—H24	119.9
C19—C7—C6	112.66 (11)	C25—C24—H24	119.9
C8—C7—C6	102.97 (11)	C24—C25—C20	121.49 (18)
N1—C8—C9	115.59 (10)	C24—C25—H25	119.3
N1—C8—C7	99.80 (10)	C20—C25—H25	119.3
C9—C8—C7	112.33 (12)	O2—C26—O3	123.07 (14)
N1—C8—H8	109.6	O2—C26—C7	124.22 (14)
C9—C8—H8	109.6	O3—C26—C7	112.70 (12)
C7—C8—H8	109.6	O3—C27—H27A	109.5
C18—C9—C10	118.14 (13)	O3—C27—H27B	109.5
C18—C9—C8	119.29 (13)	H27A—C27—H27B	109.5
C10—C9—C8	122.39 (13)	O3—C27—H27C	109.5
C11—C10—C15	117.06 (15)	H27A—C27—H27C	109.5
C11—C10—C9	123.40 (14)	H27B—C27—H27C	109.5
C15—C10—C9	119.52 (15)	C1—N1—C5	110.91 (11)
C12—C11—C10	121.81 (17)	C1—N1—C8	116.93 (11)
C12—C11—H11	119.1	C5—N1—C8	104.15 (10)
C10—C11—H11	119.1	C18—O1—C19	116.88 (12)
C11—C12—C13	120.7 (2)	C26—O3—C27	116.46 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O3	0.98	2.47	2.8240 (19)	101
C19—H19B···N1	0.97	2.55	2.885 (2)	100

Experimental details

Crystal data
Chemical formula	C₂₇H₂₇NO₃
M_r	413.50
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.4201 (3), 10.6752 (3), 11.0761 (3)
α, β, γ (°)	78.262 (2), 77.911 (2), 87.346 (2)
V (Å³)	1066.34 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.20 × 0.15

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.975, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	22685, 4641, 3461
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.122, 1.00
No. of reflections	4641
No. of parameters	281
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.23

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).