1′-Methyl-4′-phenyldispiro­[indan-2,2′-pyrrolidine-3′,2′′-indan]-1,3,1′′-trione

Wei, A.C.; Ali, M.A.; Choon, T.S.; Quah, C.K.; Fun, H.-K.

doi:10.1107/S1600536811032934

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2383

doi:10.1107/S1600536811032934

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1′-Methyl-4′-phenyldispiro[indan-2,2′-pyrrolidine-3′,2′′-indan]-1,3,1′′-trione

Ang Chee Wei,^a Mohamed Ashraf Ali,^a Tan Soo Choon,^a Ching Kheng Quah ^b ‡ and Hoong-Kun Fun ^b ^*§

^aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 12 August 2011; accepted 14 August 2011; online 27 August 2011)

The conformation of the title compound, C₂₇H₂₁NO₃, is stabilized by a weak intramolecular C—H⋯O hydrogen bond, which generates an S(6) ring motif. The pyrrolidine ring adopts a half-chair conformation. Both of the other five-membered rings are in envelope conformations. No significant intermolecular hydrogen bonds are observed.

Related literature

For general background to and the biological activity of the title compound, see: Amalraj et al. (2003 ); Karthikeyan et al. (2010 ); Chande et al. (2005 ); Sriram et al. (2009 ); Duncan & Barry (2004 ). For reference bond-length data, see: Allen et al. (1987 ). For related structures, see: Kumar et al. (2010 ); Wei et al. (2011 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For ring conformations, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₇H₂₁NO₃
M_r = 407.45
Monoclinic, P 2₁ /c
a = 8.4578 (7) Å
b = 11.6194 (9) Å
c = 22.6360 (16) Å
β = 109.693 (2)°
V = 2094.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.34 × 0.26 × 0.15 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.972, T_max = 0.988
23854 measured reflections
6084 independent reflections
3982 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.163
S = 1.03
6084 reflections
281 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C27—H27A⋯O2	0.97	2.42	3.069 (2)	124

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811032934/wn2448sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811032934/wn2448Isup2.hkl

checkCIF report

Comment top

Heterocyclic compounds, especially those with five- and six-membered rings have received considerable attention as a result of their diverse biological activities (Amalraj et al., 2003). Substituted pyrrolidine analogues have high potential in the treatment of tuberculosis (TB) (Karthikeyan et al., 2010). Tuberculosis, an illness caused by Mycobacterium tuberculosis, is the leading cause of worldwide death from infectious diseases (Chande et al., 2005). Problems arise when patients develop bacterial resistance to the first-line drugs and the second-line drugs are too toxic and cannot be employed simultaneously (Sriram et al., 2009). Therefore, there is an impetus for the development of new antitubercular agents to shorten the treatment regime and which are effective against drug-resistant strains of M. tuberculosis (Duncan & Barry, 2004).

The molecular structure is shown in Fig. 1. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to those in related crystal structures (Kumar et al., 2010; Wei et al., 2011).

The pyrrolidine ring (N1/C7/C8/C10/C19) is twisted about the C10—C19 bond, with puckering parameters (Cremer & Pople, 1975) Q = 0.4335 (17) Å and ϕ = 126.7 (2)°, thereby adopting a half-chair conformation. The two five-membered carbocyclic rings, C10-C12/C17/C18 and C19-C21/C26/C27, are in envelope conformations: puckering parameters Q = 0.1992 (17) Å and ϕ = 179.8 (5)° with atom C10 at the flap; and Q = 0.1879 (16) Å and ϕ = 355.8 (5)° with atom C19 at the flap, respectively.

If the three benzene rings C1–C6, C12–C17 and C21–C26 are denoted by R4, R5, R6 then the dihedral angles for R4^R5, R5^R6 and R4^R6 are 79.88 (11), 34.21 (9) and 82.39 (12)°, respectively.

The molecular structure is stabilized by an intramolecular C27–H27A···O2 hydrogen bond (Table 1), which generates an S(6) ring motif (Fig. 1, Bernstein et al., 1995). No significant intermolecular hydrogen bond is observed. There is a short contact of 1.94 Å between H5A and H8B.

Related literature top

For general background to and the biological activity of the title compound, see: Amalraj et al. (2003); Karthikeyan et al. (2010); Chande et al. (2005); Sriram et al. (2009); Duncan & Barry (2004). For reference bond-length data, see: Allen et al. (1987). For related structures, see: Kumar et al. (2010); Wei et al. (2011). For hydrogen-bond motifs, see: Bernstein et al. (1995). For ring conformations, see: Cremer & Pople (1975).

Experimental top

A mixture of (E)-(2-benzylidene)-2,3-dihydro-IH-indene-1-one (0.001 mmol), ninhydrin (0.001 mmol) and sarcosine (0.002 mmol) (1:1:2) was dissolved in methanol (10 ml) and refluxed for 4 h. After completion of the reaction, as evident from TLC, the mixture was poured into water (50 ml). The precipitated solid was filtered, washed with water and recrystallised from a pet. ether - ethyl acetate mixture (1:1) to yield the title compound as yellow crystals.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids for non-H atoms. The intramolecular hydrogen bond is shown as a dashed line.

1'-Methyl-4'-phenyldispiro[indan-2,2'-pyrrolidine-3',2''-indan]-1,3,1''-trione top

Crystal data top

C₂₇H₂₁NO₃	F(000) = 856
M_r = 407.45	D_x = 1.292 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5963 reflections
a = 8.4578 (7) Å	θ = 2.6–28.2°
b = 11.6194 (9) Å	µ = 0.08 mm⁻¹
c = 22.6360 (16) Å	T = 296 K
β = 109.693 (2)°	Block, yellow
V = 2094.4 (3) Å³	0.34 × 0.26 × 0.15 mm
Z = 4

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	6084 independent reflections
Radiation source: fine-focus sealed tube	3982 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 30.1°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
T_min = 0.972, T_max = 0.988	k = −15→16
23854 measured reflections	l = −31→31

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.163	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0731P)² + 0.4081P] where P = (F_o² + 2F_c²)/3
6084 reflections	(Δ/σ)_max = 0.001
281 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₇H₂₁NO₃	V = 2094.4 (3) Å³
M_r = 407.45	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.4578 (7) Å	µ = 0.08 mm⁻¹
b = 11.6194 (9) Å	T = 296 K
c = 22.6360 (16) Å	0.34 × 0.26 × 0.15 mm
β = 109.693 (2)°

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	6084 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3982 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.988	R_int = 0.035
23854 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.163	H-atom parameters constrained
S = 1.03	Δρ_max = 0.20 e Å⁻³
6084 reflections	Δρ_min = −0.21 e Å⁻³
281 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	1.34827 (16)	0.31094 (11)	0.95641 (6)	0.0717 (4)
O2	1.00814 (19)	0.39487 (11)	0.75292 (5)	0.0679 (4)
O3	0.98637 (17)	0.36481 (11)	0.97255 (5)	0.0622 (3)
N1	1.15973 (17)	0.19994 (11)	0.83324 (7)	0.0517 (3)
C1	0.7927 (4)	0.0968 (2)	0.94738 (12)	0.0926 (8)
H1A	0.8054	0.1696	0.9654	0.111*
C2	0.6731 (4)	0.0227 (2)	0.95567 (14)	0.1032 (9)
H2A	0.6047	0.0476	0.9778	0.124*
C3	0.6549 (3)	−0.0845 (2)	0.93209 (12)	0.0863 (7)
H3A	0.5778	−0.1352	0.9390	0.104*
C4	0.7512 (4)	−0.1166 (2)	0.89819 (17)	0.1153 (10)
H4A	0.7393	−0.1902	0.8812	0.138*
C5	0.8678 (3)	−0.04216 (18)	0.88813 (14)	0.0938 (8)
H5A	0.9306	−0.0661	0.8637	0.113*
C6	0.89185 (19)	0.06577 (13)	0.91353 (7)	0.0457 (3)
C7	1.02348 (18)	0.14830 (12)	0.90680 (7)	0.0415 (3)
H7A	1.0976	0.1668	0.9494	0.050*
C8	1.1369 (2)	0.10356 (15)	0.87084 (10)	0.0607 (5)
H8A	1.2442	0.0783	0.8999	0.073*
H8B	1.0839	0.0394	0.8441	0.073*
C9	1.3153 (3)	0.2003 (2)	0.81922 (12)	0.0852 (7)
H9A	1.3127	0.2618	0.7906	0.128*
H9B	1.3275	0.1282	0.8005	0.128*
H9C	1.4084	0.2112	0.8573	0.128*
C10	1.11262 (17)	0.30515 (12)	0.85686 (7)	0.0414 (3)
C11	1.24588 (18)	0.36203 (13)	0.91420 (7)	0.0466 (3)
C12	1.22771 (17)	0.48842 (13)	0.90556 (7)	0.0424 (3)
C13	1.2992 (2)	0.57672 (14)	0.94769 (8)	0.0504 (4)
H13A	1.3671	0.5608	0.9886	0.060*
C14	1.2661 (2)	0.68821 (15)	0.92684 (9)	0.0575 (4)
H14A	1.3126	0.7485	0.9542	0.069*
C15	1.1648 (2)	0.71263 (15)	0.86571 (9)	0.0599 (4)
H15A	1.1453	0.7889	0.8529	0.072*
C16	1.0922 (2)	0.62575 (14)	0.82347 (8)	0.0523 (4)
H16A	1.0239	0.6422	0.7826	0.063*
C17	1.12528 (18)	0.51301 (13)	0.84439 (7)	0.0428 (3)
C18	1.07040 (19)	0.40499 (14)	0.80921 (7)	0.0461 (3)
C19	0.95609 (16)	0.26431 (12)	0.87430 (6)	0.0378 (3)
C20	0.91217 (19)	0.35346 (12)	0.91692 (7)	0.0428 (3)
C21	0.76765 (19)	0.42024 (13)	0.87730 (8)	0.0477 (4)
C22	0.7002 (3)	0.52158 (15)	0.89235 (11)	0.0663 (5)
H22A	0.7461	0.5559	0.9316	0.080*
C23	0.5639 (3)	0.5683 (2)	0.84708 (15)	0.0856 (7)
H23A	0.5155	0.6354	0.8555	0.103*
C24	0.4974 (3)	0.5161 (2)	0.78866 (14)	0.0898 (8)
H24A	0.4044	0.5491	0.7588	0.108*
C25	0.5656 (2)	0.41625 (19)	0.77349 (10)	0.0710 (6)
H25A	0.5206	0.3829	0.7340	0.085*
C26	0.70320 (18)	0.36772 (13)	0.81919 (8)	0.0477 (4)
C27	0.79686 (18)	0.25889 (13)	0.81565 (7)	0.0456 (3)
H27A	0.8256	0.2571	0.7776	0.055*
H27B	0.7304	0.1914	0.8167	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0569 (7)	0.0572 (7)	0.0736 (8)	−0.0085 (6)	−0.0143 (6)	0.0166 (6)
O2	0.0945 (10)	0.0639 (8)	0.0383 (6)	−0.0176 (7)	0.0131 (6)	0.0000 (5)
O3	0.0805 (8)	0.0580 (7)	0.0440 (7)	−0.0050 (6)	0.0155 (6)	−0.0125 (5)
N1	0.0550 (7)	0.0446 (7)	0.0638 (9)	−0.0008 (6)	0.0309 (7)	−0.0027 (6)
C1	0.128 (2)	0.0670 (13)	0.119 (2)	−0.0339 (13)	0.0878 (18)	−0.0193 (13)
C2	0.122 (2)	0.0954 (19)	0.125 (2)	−0.0344 (16)	0.0859 (18)	−0.0022 (16)
C3	0.0723 (13)	0.0836 (16)	0.0965 (17)	−0.0276 (12)	0.0200 (12)	0.0272 (13)
C4	0.119 (2)	0.0597 (14)	0.181 (3)	−0.0419 (14)	0.069 (2)	−0.0216 (17)
C5	0.0971 (16)	0.0507 (11)	0.155 (2)	−0.0228 (11)	0.0698 (17)	−0.0251 (13)
C6	0.0477 (7)	0.0391 (7)	0.0461 (8)	−0.0035 (6)	0.0103 (6)	0.0053 (6)
C7	0.0449 (7)	0.0352 (7)	0.0431 (8)	−0.0017 (5)	0.0130 (6)	0.0005 (6)
C8	0.0684 (11)	0.0437 (9)	0.0810 (13)	0.0068 (8)	0.0396 (10)	0.0044 (8)
C9	0.0804 (14)	0.0779 (14)	0.122 (2)	0.0045 (11)	0.0670 (14)	0.0036 (13)
C10	0.0420 (7)	0.0378 (7)	0.0428 (8)	−0.0054 (5)	0.0120 (6)	−0.0010 (6)
C11	0.0398 (7)	0.0463 (8)	0.0475 (8)	−0.0071 (6)	0.0064 (6)	0.0056 (7)
C12	0.0391 (6)	0.0417 (7)	0.0457 (8)	−0.0060 (6)	0.0131 (6)	0.0017 (6)
C13	0.0497 (8)	0.0520 (9)	0.0476 (8)	−0.0098 (7)	0.0139 (7)	−0.0029 (7)
C14	0.0677 (10)	0.0469 (9)	0.0613 (11)	−0.0081 (8)	0.0260 (9)	−0.0119 (8)
C15	0.0736 (11)	0.0420 (9)	0.0670 (11)	0.0037 (8)	0.0275 (9)	0.0034 (8)
C16	0.0571 (9)	0.0498 (9)	0.0498 (9)	0.0016 (7)	0.0176 (7)	0.0083 (7)
C17	0.0429 (7)	0.0429 (8)	0.0426 (8)	−0.0046 (6)	0.0146 (6)	0.0033 (6)
C18	0.0485 (8)	0.0489 (8)	0.0396 (8)	−0.0080 (6)	0.0132 (6)	0.0010 (6)
C19	0.0380 (6)	0.0349 (7)	0.0383 (7)	−0.0038 (5)	0.0098 (5)	−0.0032 (5)
C20	0.0477 (7)	0.0362 (7)	0.0453 (8)	−0.0065 (6)	0.0170 (6)	−0.0035 (6)
C21	0.0480 (8)	0.0405 (8)	0.0611 (10)	0.0006 (6)	0.0267 (7)	0.0062 (7)
C22	0.0780 (12)	0.0463 (9)	0.0926 (14)	0.0087 (8)	0.0524 (11)	0.0089 (9)
C23	0.0805 (14)	0.0618 (13)	0.134 (2)	0.0262 (11)	0.0619 (16)	0.0306 (14)
C24	0.0582 (11)	0.0838 (16)	0.129 (2)	0.0260 (11)	0.0339 (13)	0.0571 (16)
C25	0.0481 (9)	0.0771 (13)	0.0796 (13)	0.0005 (9)	0.0108 (9)	0.0307 (11)
C26	0.0370 (7)	0.0469 (8)	0.0578 (9)	−0.0028 (6)	0.0141 (6)	0.0135 (7)
C27	0.0434 (7)	0.0443 (8)	0.0428 (8)	−0.0079 (6)	0.0064 (6)	−0.0026 (6)

Geometric parameters (Å, º) top

O1—C11	1.2073 (18)	C11—C12	1.483 (2)
O2—C18	1.2092 (18)	C12—C13	1.393 (2)
O3—C20	1.2102 (18)	C12—C17	1.393 (2)
N1—C10	1.4432 (19)	C13—C14	1.375 (2)
N1—C9	1.454 (2)	C13—H13A	0.9300
N1—C8	1.459 (2)	C14—C15	1.389 (3)
C1—C6	1.362 (3)	C14—H14A	0.9300
C1—C2	1.388 (3)	C15—C16	1.384 (2)
C1—H1A	0.9300	C15—H15A	0.9300
C2—C3	1.344 (4)	C16—C17	1.389 (2)
C2—H2A	0.9300	C16—H16A	0.9300
C3—C4	1.346 (4)	C17—C18	1.475 (2)
C3—H3A	0.9300	C19—C27	1.5411 (19)
C4—C5	1.387 (3)	C19—C20	1.5438 (19)
C4—H4A	0.9300	C20—C21	1.470 (2)
C5—C6	1.366 (3)	C21—C26	1.384 (2)
C5—H5A	0.9300	C21—C22	1.400 (2)
C6—C7	1.515 (2)	C22—C23	1.370 (3)
C7—C8	1.542 (2)	C22—H22A	0.9300
C7—C19	1.549 (2)	C23—C24	1.390 (4)
C7—H7A	0.9800	C23—H23A	0.9300
C8—H8A	0.9700	C24—C25	1.390 (3)
C8—H8B	0.9700	C24—H24A	0.9300
C9—H9A	0.9600	C25—C26	1.389 (2)
C9—H9B	0.9600	C25—H25A	0.9300
C9—H9C	0.9600	C26—C27	1.508 (2)
C10—C18	1.542 (2)	C27—H27A	0.9700
C10—C11	1.551 (2)	C27—H27B	0.9700
C10—C19	1.5766 (19)

C10—N1—C9	117.49 (14)	C14—C13—C12	117.91 (16)
C10—N1—C8	109.06 (12)	C14—C13—H13A	121.0
C9—N1—C8	115.95 (15)	C12—C13—H13A	121.0
C6—C1—C2	121.8 (2)	C13—C14—C15	121.34 (16)
C6—C1—H1A	119.1	C13—C14—H14A	119.3
C2—C1—H1A	119.1	C15—C14—H14A	119.3
C3—C2—C1	120.8 (2)	C16—C15—C14	121.36 (16)
C3—C2—H2A	119.6	C16—C15—H15A	119.3
C1—C2—H2A	119.6	C14—C15—H15A	119.3
C2—C3—C4	118.2 (2)	C15—C16—C17	117.45 (15)
C2—C3—H3A	120.9	C15—C16—H16A	121.3
C4—C3—H3A	120.9	C17—C16—H16A	121.3
C3—C4—C5	121.4 (2)	C16—C17—C12	121.24 (14)
C3—C4—H4A	119.3	C16—C17—C18	128.89 (14)
C5—C4—H4A	119.3	C12—C17—C18	109.83 (13)
C6—C5—C4	121.1 (2)	O2—C18—C17	126.70 (14)
C6—C5—H5A	119.4	O2—C18—C10	125.44 (14)
C4—C5—H5A	119.4	C17—C18—C10	107.82 (12)
C1—C6—C5	116.57 (17)	C27—C19—C20	103.96 (11)
C1—C6—C7	120.11 (15)	C27—C19—C7	116.64 (11)
C5—C6—C7	123.30 (16)	C20—C19—C7	114.48 (12)
C6—C7—C8	116.63 (13)	C27—C19—C10	111.13 (11)
C6—C7—C19	115.67 (12)	C20—C19—C10	110.71 (11)
C8—C7—C19	103.73 (12)	C7—C19—C10	100.09 (11)
C6—C7—H7A	106.7	O3—C20—C21	127.61 (14)
C8—C7—H7A	106.7	O3—C20—C19	125.02 (14)
C19—C7—H7A	106.7	C21—C20—C19	107.37 (12)
N1—C8—C7	106.11 (12)	C26—C21—C22	122.67 (16)
N1—C8—H8A	110.5	C26—C21—C20	109.10 (13)
C7—C8—H8A	110.5	C22—C21—C20	128.23 (17)
N1—C8—H8B	110.5	C23—C22—C21	117.4 (2)
C7—C8—H8B	110.5	C23—C22—H22A	121.3
H8A—C8—H8B	108.7	C21—C22—H22A	121.3
N1—C9—H9A	109.5	C22—C23—C24	120.5 (2)
N1—C9—H9B	109.5	C22—C23—H23A	119.7
H9A—C9—H9B	109.5	C24—C23—H23A	119.7
N1—C9—H9C	109.5	C23—C24—C25	122.1 (2)
H9A—C9—H9C	109.5	C23—C24—H24A	119.0
H9B—C9—H9C	109.5	C25—C24—H24A	119.0
N1—C10—C18	113.94 (12)	C26—C25—C24	117.9 (2)
N1—C10—C11	117.22 (13)	C26—C25—H25A	121.0
C18—C10—C11	101.33 (11)	C24—C25—H25A	121.0
N1—C10—C19	101.41 (11)	C21—C26—C25	119.43 (17)
C18—C10—C19	112.68 (12)	C21—C26—C27	111.98 (13)
C11—C10—C19	110.70 (11)	C25—C26—C27	128.58 (17)
O1—C11—C12	127.32 (14)	C26—C27—C19	104.01 (12)
O1—C11—C10	125.30 (15)	C26—C27—H27A	111.0
C12—C11—C10	107.33 (12)	C19—C27—H27A	111.0
C13—C12—C17	120.70 (14)	C26—C27—H27B	111.0
C13—C12—C11	129.62 (14)	C19—C27—H27B	111.0
C17—C12—C11	109.66 (13)	H27A—C27—H27B	109.0

C6—C1—C2—C3	2.3 (5)	N1—C10—C18—O2	32.0 (2)
C1—C2—C3—C4	−2.5 (5)	C11—C10—C18—O2	158.81 (16)
C2—C3—C4—C5	0.7 (5)	C19—C10—C18—O2	−82.9 (2)
C3—C4—C5—C6	1.5 (5)	N1—C10—C18—C17	−145.92 (13)
C2—C1—C6—C5	0.0 (4)	C11—C10—C18—C17	−19.09 (15)
C2—C1—C6—C7	−178.7 (2)	C19—C10—C18—C17	99.24 (14)
C4—C5—C6—C1	−1.8 (4)	C6—C7—C19—C27	−42.73 (18)
C4—C5—C6—C7	176.8 (2)	C8—C7—C19—C27	86.27 (15)
C1—C6—C7—C8	176.65 (19)	C6—C7—C19—C20	78.95 (15)
C5—C6—C7—C8	−1.9 (3)	C8—C7—C19—C20	−152.06 (13)
C1—C6—C7—C19	−61.0 (2)	C6—C7—C19—C10	−162.65 (12)
C5—C6—C7—C19	120.5 (2)	C8—C7—C19—C10	−33.65 (14)
C10—N1—C8—C7	16.59 (18)	N1—C10—C19—C27	−80.25 (14)
C9—N1—C8—C7	151.92 (17)	C18—C10—C19—C27	41.96 (16)
C6—C7—C8—N1	140.91 (14)	C11—C10—C19—C27	154.64 (12)
C19—C7—C8—N1	12.50 (17)	N1—C10—C19—C20	164.75 (12)
C9—N1—C10—C18	66.1 (2)	C18—C10—C19—C20	−73.04 (15)
C8—N1—C10—C18	−159.39 (14)	C11—C10—C19—C20	39.63 (16)
C9—N1—C10—C11	−52.0 (2)	N1—C10—C19—C7	43.60 (13)
C8—N1—C10—C11	82.57 (16)	C18—C10—C19—C7	165.81 (12)
C9—N1—C10—C19	−172.61 (16)	C11—C10—C19—C7	−81.52 (13)
C8—N1—C10—C19	−38.06 (16)	C27—C19—C20—O3	162.64 (14)
N1—C10—C11—O1	−34.0 (2)	C7—C19—C20—O3	34.26 (19)
C18—C10—C11—O1	−158.66 (17)	C10—C19—C20—O3	−77.95 (18)
C19—C10—C11—O1	81.6 (2)	C27—C19—C20—C21	−17.88 (14)
N1—C10—C11—C12	143.58 (13)	C7—C19—C20—C21	−146.26 (12)
C18—C10—C11—C12	18.94 (15)	C10—C19—C20—C21	101.54 (13)
C19—C10—C11—C12	−100.80 (14)	O3—C20—C21—C26	−169.99 (15)
O1—C11—C12—C13	−13.2 (3)	C19—C20—C21—C26	10.55 (16)
C10—C11—C12—C13	169.23 (15)	O3—C20—C21—C22	10.7 (3)
O1—C11—C12—C17	165.01 (17)	C19—C20—C21—C22	−168.81 (15)
C10—C11—C12—C17	−12.52 (16)	C26—C21—C22—C23	0.6 (2)
C17—C12—C13—C14	−0.4 (2)	C20—C21—C22—C23	179.92 (17)
C11—C12—C13—C14	177.69 (16)	C21—C22—C23—C24	−0.3 (3)
C12—C13—C14—C15	0.0 (2)	C22—C23—C24—C25	−0.5 (3)
C13—C14—C15—C16	0.4 (3)	C23—C24—C25—C26	0.9 (3)
C14—C15—C16—C17	−0.3 (3)	C22—C21—C26—C25	−0.2 (2)
C15—C16—C17—C12	0.0 (2)	C20—C21—C26—C25	−179.63 (14)
C15—C16—C17—C18	−177.50 (16)	C22—C21—C26—C27	−179.01 (14)
C13—C12—C17—C16	0.4 (2)	C20—C21—C26—C27	1.59 (17)
C11—C12—C17—C16	−178.01 (14)	C24—C25—C26—C21	−0.5 (3)
C13—C12—C17—C18	178.31 (13)	C24—C25—C26—C27	178.03 (16)
C11—C12—C17—C18	−0.12 (17)	C21—C26—C27—C19	−12.89 (16)
C16—C17—C18—O2	12.6 (3)	C25—C26—C27—C19	168.47 (16)
C12—C17—C18—O2	−165.04 (16)	C20—C19—C27—C26	18.05 (14)
C16—C17—C18—C10	−169.50 (15)	C7—C19—C27—C26	145.09 (12)
C12—C17—C18—C10	12.82 (16)	C10—C19—C27—C26	−101.08 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C27—H27A···O2	0.97	2.42	3.069 (2)	124

Experimental details

Crystal data
Chemical formula	C₂₇H₂₁NO₃
M_r	407.45
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.4578 (7), 11.6194 (9), 22.6360 (16)
β (°)	109.693 (2)
V (Å³)	2094.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.34 × 0.26 × 0.15

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.972, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	23854, 6084, 3982
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.163, 1.03
No. of reflections	6084
No. of parameters	281
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.21

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C27—H27A···O2	0.97	2.42	3.069 (2)	124

Footnotes

‡Thomson Reuters ResearcherID: A-5525-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM), Penang, Malaysia for providing research facilities. HKF and CKQ also thank USM for the Research University Grant (No. 1001/PFIZIK/811160).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Amalraj, A., Raghunathan, R., Sridevi Kumari, M. R. & Raman, N. (2003). Bioorg. Med. Chem. 11, 407–419. Web of Science PubMed Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chamg, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chande, M. S., Verma, R. S., Barve, P. A. & Khanwelkar, R. R. (2005). Eur. J. Med. Chem. 40, 1143–1148. Web of Science CrossRef PubMed CAS Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Duncan, K. & Barry, C. E. (2004). Curr Opin Microbiol. 7, 460–465. CrossRef CAS Google Scholar
Karthikeyan, S. V., Devi Bala, B., Alex Raja, V. P., Perumal, S., Yogeeswari, P. & Sriram, D. (2010). Bioorg. Med. Chem. Lett. 20, 350–353. CrossRef CAS Google Scholar
Kumar, R. S., Osman, H., Ali, M. A., Quah, C. K. & Fun, H.-K. (2010). Acta Cryst. E66, o1540–o1541. Web of Science CSD CrossRef IUCr Journals 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
Sriram, D., Yogeeswari, P. & Priya, D. Y. (2009). Biomed. Pharmacother. 63, 36–39. CAS Google Scholar
Wei, A. C., Ali, M. A., Ismail, R., Quah, C. K. & Fun, H.-K. (2011). Acta Cryst. E67, o2381–o2382. Web of Science CSD CrossRef IUCr Journals Google Scholar

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