8-Meth­oxy-3,3,5-trimethyl-3,11-dihydro­pyrano[3,2-a]carbazole

Uvarani, C.; Ramesh, P.; Ravichandran, K.; Mohan, P.S.; Ponnuswamy, M.N.

doi:10.1107/S160053681002074X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1581

doi:10.1107/S160053681002074X

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8-Methoxy-3,3,5-trimethyl-3,11-dihydropyrano[3,2-a]carbazole

C. Uvarani,^a P. Ramesh,^b K. Ravichandran,^b P. S. Mohan ^a and M. N. Ponnuswamy ^b ^*

^aDepartment of Chemistry, School of Chemical Sciences, Bharathiar University, Coimbatore 641 046, India, and ^bCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 17 May 2010; accepted 31 May 2010; online 5 June 2010)

In the title compound, C₁₉H₁₉NO₂, commonly called koenimbine, the pyran ring adopts a sofa conformation. The carbazole ring system is planar [r.m.s. deviation = 0.063 (1) Å]. A C(10) zigzag chain running along the b axis is formed through intermolecular C—H⋯O hydrogen bonds. The chains are linked via weak C—H⋯π and N—H⋯π interactions.

Related literature

For bond-length data, see: Allen et al. (1987 ). For the biological activity of carbazole derivatives, see: Kong et al. (1986 ); Ito (2000 ); Ramsewak et al. (1999 ); Chowdhury et al. (2001 ); Fiebi et al. (1985 ). For puckering parameters, see: Cremer & Pople (1975 ). For asymmetry parameters, see: Nardelli (1983 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₉H₁₉NO₂
M_r = 293.35
Monoclinic, P 2₁ /c
a = 8.290 (5) Å
b = 8.693 (5) Å
c = 21.326 (5) Å
β = 90.742 (5)°
V = 1536.7 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.20 × 0.17 × 0.16 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.984, T_max = 0.987
14325 measured reflections
3803 independent reflections
3050 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.137
S = 1.05
3803 reflections
207 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C2/C7/C8/C16 ring and Cg4 is the centroid of the C8–C11/C15/C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1ⁱ	0.93	2.54	3.333 (2)	143
N1—H1⋯Cg4ⁱⁱ	0.872 (18)	2.744 (17)	3.528 (2)	149.7 (14)
C17—H17C⋯Cg1ⁱⁱⁱ	0.96	3.08	3.489 (3)	107
C17—H17C⋯Cg4ⁱⁱⁱ	0.96	3.00	3.514 (3)	115
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); 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 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681002074X/sj5011sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681002074X/sj5011Isup2.hkl

checkCIF report

Comment top

Murraya koenigii (L.) Spreng (Family of Rutaceae), commonly known as the Indian curry leaf plant, is cultivated for the aromatic and appetizing nature of its leaves. The leaves are used for flavouring southern Asian dishes. Various parts of the plant have been used in traditional or folk medicine for the treatment of head-, tooth-, and stomach aches, influenza, rheumatism, traumatic injury, insect and snake bites, and also as an antidysentric as well as an astringent (Kong et al., 1986). Recently, several biological activities have been reported for carbazole alkaloids. Bioactive coumarins, acridone alkaloids and carbazole alkaloids from the family of Rutaceae were reviewed (Ito, 2000). Mahanimbine, murrayanol, and mahanine compounds isolated from M. koenigii exhibit antioxidant, mosquitocidal and antimicrobial activities (Ramsewak et al.., 1999). Activities of carbazoles from M. koenigii against Gram-positive and Gram-negative bacteria and fungi were reported (Chowdhury et al., 2001). The ethanol extract of M. koenigii displayed cytotoxic activity against cultured KB cells (Fiebi et al., 1985). Against this background and to ascertain the structure and molecular conformation, the X-ray structure determination of the title compound has been carried out.

An ORTEP plot of the molecule is shown in Fig. 1. The carbazole ring system is planar (r.m.s. deviation 0.016 Å). The pyran ring in the molecule adopts sofa conformation with the puckering parameters (Cremer & Pople, 1975) and asymmetry parameters (Nardelli, 1983): q₂ = 0.287 (1) Å, q₃ = -0.126 (1) Å, ϕ₂ = 136.6 (3)° and Δ_s(C12 & C15)= 10.9 (2)°. The N—C bond lengths, namely N1—C2 and N1—C16 [1.386 (2) & 1.383 (2) Å] deviate slightly from the mean value reported in the literature 1.370 (12) Å (Allen et al., 1987). The sum of the bond angles around N1 [359.3°] is in accordance with sp² hybridization. The methoxy group substituted at C5 deviates slightly from the plane of the attached carbazole ring system [C6—C5—O2—C17 = 19.3 (2)°].

The crystal packing of the molecules is controlled by C–H···O and C—H··· π types of intermolecular interactions. Atom C8 of the molecule at (x, y, z) donates a proton to atom O1 of the molecule at (-x+2, y+1/2, -z+1/2+1), which form a one dimensional zigzag C(10) chain (Bernstein et al., 1995) running along the b–axis, Fig. 2. The packing of the molecules is further influenced by C—H··· π contacts and an N1—H1···Cg4 interaction of Table 1; Cg4 is the centroid of the C8/C9/C10/C11/C15/C16 benzene ring.

Related literature top

For bond-length data, see: Allen et al. (1987). For the biological activity of carbazole derivatives, see: Kong et al. (1986); Ito (2000); Ramsewak et al. (1999); Chowdhury et al. (2001); Fiebi et al. (1985). For puckering parameters, see: Cremer & Pople (1975). For asymmetry parameters, see: Nardelli (1983). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

The air dried fruit pulps of M. koenigii were extracted with n-hexane in a Soxhlet apparatus. The total extract was concentrated and kept at room temperature. A dirty white solid separated out. This was dissolved in chloroform and chromatographed using a silica gel column and eluted successively with n-hexane and n-hexane- chloroform mixture. The fraction obtained with 7% chloroform in hexane afforded a white crystalline solid. Which on repeated crystallization with methanol:chloroform (3:1) as solvent afforded white crystalline solid koenimbine (3,11-Dihydro-8-methoxy-3,3,5- trimethylpyrano[3,2-a]carbazole).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atomic numbering and with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The crystal packing of the title compound. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.

8-Methoxy-3,3,5-trimethyl-3,11-dihydropyrano[3,2-a]carbazole top

Crystal data top

C₁₉H₁₉NO₂	F(000) = 624
M_r = 293.35	D_x = 1.268 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1546 reflections
a = 8.290 (5) Å	θ = 1.9–28.3°
b = 8.693 (5) Å	µ = 0.08 mm⁻¹
c = 21.326 (5) Å	T = 293 K
β = 90.742 (5)°	Block, colorless
V = 1536.7 (13) Å³	0.20 × 0.17 × 0.16 mm
Z = 4

Data collection top

Bruker SMART APEXII area-detector diffractometer	3803 independent reflections
Radiation source: fine-focus sealed tube	3050 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω and ϕ scans	θ_max = 28.3°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→11
T_min = 0.984, T_max = 0.987	k = −9→11
14325 measured reflections	l = −28→28

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0713P)² + 0.2629P] where P = (F_o² + 2F_c²)/3
3803 reflections	(Δ/σ)_max = 0.004
207 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₉H₁₉NO₂	V = 1536.7 (13) Å³
M_r = 293.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.290 (5) Å	µ = 0.08 mm⁻¹
b = 8.693 (5) Å	T = 293 K
c = 21.326 (5) Å	0.20 × 0.17 × 0.16 mm
β = 90.742 (5)°

Data collection top

Bruker SMART APEXII area-detector diffractometer	3803 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3050 reflections with I > 2σ(I)
T_min = 0.984, T_max = 0.987	R_int = 0.026
14325 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.24 e Å⁻³
3803 reflections	Δρ_min = −0.22 e Å⁻³
207 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 > 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
O1	1.12605 (11)	0.25969 (10)	0.57699 (4)	0.0444 (2)
O2	0.32475 (14)	0.26609 (14)	0.86787 (5)	0.0676 (3)
N1	0.93165 (14)	0.40700 (14)	0.78439 (5)	0.0436 (3)
C2	0.78388 (15)	0.37981 (14)	0.81195 (6)	0.0396 (3)
C3	0.72718 (17)	0.42649 (16)	0.87003 (6)	0.0468 (3)
H3	0.7911	0.4851	0.8971	0.056*
C4	0.57398 (18)	0.38336 (16)	0.88612 (6)	0.0487 (3)
H4	0.5338	0.4134	0.9248	0.058*
C5	0.47677 (16)	0.29541 (15)	0.84589 (6)	0.0451 (3)
C6	0.53268 (16)	0.24753 (14)	0.78823 (6)	0.0407 (3)
H6	0.4684	0.1883	0.7616	0.049*
C7	0.68785 (15)	0.29046 (14)	0.77121 (5)	0.0368 (3)
C8	0.78297 (14)	0.26342 (13)	0.71591 (5)	0.0360 (3)
C9	0.75455 (14)	0.18608 (15)	0.65939 (6)	0.0381 (3)
H9	0.6579	0.1337	0.6532	0.046*
C10	0.86873 (15)	0.18656 (14)	0.61251 (5)	0.0381 (3)
C11	1.01461 (15)	0.26595 (13)	0.62376 (6)	0.0364 (3)
C12	1.25668 (16)	0.37274 (16)	0.57659 (7)	0.0472 (3)
C13	1.31224 (18)	0.40802 (18)	0.64208 (8)	0.0561 (4)
H13	1.4190	0.4368	0.6492	0.067*
C14	1.21332 (16)	0.39936 (17)	0.69017 (7)	0.0493 (3)
H14	1.2471	0.4319	0.7298	0.059*
C15	1.05153 (14)	0.33853 (14)	0.68064 (6)	0.0377 (3)
C16	0.93148 (14)	0.33859 (14)	0.72584 (5)	0.0369 (3)
C17	0.23594 (19)	0.1452 (2)	0.84007 (8)	0.0625 (4)
H17A	0.2161	0.1681	0.7966	0.094*
H17B	0.1350	0.1338	0.8611	0.094*
H17C	0.2963	0.0512	0.8435	0.094*
C18	0.83971 (18)	0.10395 (18)	0.55133 (6)	0.0512 (3)
H18A	0.8971	0.0081	0.5517	0.077*
H18B	0.8771	0.1665	0.5174	0.077*
H18C	0.7264	0.0846	0.5459	0.077*
C19	1.38727 (19)	0.2969 (2)	0.53819 (8)	0.0624 (4)
H19A	1.4205	0.2029	0.5582	0.094*
H19B	1.4780	0.3650	0.5352	0.094*
H19C	1.3459	0.2747	0.4969	0.094*
C20	1.1956 (2)	0.5186 (2)	0.54519 (9)	0.0694 (5)
H20A	1.1633	0.4962	0.5028	0.104*
H20B	1.2800	0.5943	0.5452	0.104*
H20C	1.1049	0.5577	0.5678	0.104*
H1	1.005 (2)	0.469 (2)	0.7994 (8)	0.063 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0402 (5)	0.0453 (5)	0.0480 (5)	−0.0053 (4)	0.0115 (4)	−0.0031 (4)
O2	0.0550 (7)	0.0727 (8)	0.0759 (7)	−0.0199 (5)	0.0296 (6)	−0.0240 (6)
N1	0.0379 (6)	0.0484 (6)	0.0446 (6)	−0.0083 (5)	0.0010 (4)	−0.0095 (5)
C2	0.0392 (7)	0.0376 (6)	0.0421 (6)	−0.0015 (5)	0.0011 (5)	−0.0026 (5)
C3	0.0519 (8)	0.0456 (7)	0.0431 (6)	−0.0064 (6)	0.0028 (5)	−0.0091 (5)
C4	0.0566 (8)	0.0456 (7)	0.0443 (6)	−0.0036 (6)	0.0118 (6)	−0.0081 (5)
C5	0.0427 (7)	0.0412 (7)	0.0516 (7)	−0.0026 (5)	0.0115 (6)	−0.0022 (5)
C6	0.0379 (7)	0.0389 (6)	0.0454 (6)	−0.0027 (5)	0.0032 (5)	−0.0035 (5)
C7	0.0363 (6)	0.0348 (6)	0.0392 (6)	0.0008 (5)	0.0012 (5)	−0.0017 (5)
C8	0.0325 (6)	0.0352 (6)	0.0402 (6)	−0.0010 (4)	0.0010 (4)	0.0000 (4)
C9	0.0320 (6)	0.0406 (6)	0.0419 (6)	−0.0044 (5)	0.0003 (5)	−0.0033 (5)
C10	0.0371 (6)	0.0372 (6)	0.0400 (6)	−0.0011 (5)	0.0007 (5)	−0.0031 (5)
C11	0.0335 (6)	0.0343 (6)	0.0416 (6)	0.0012 (4)	0.0049 (5)	0.0017 (5)
C12	0.0375 (7)	0.0454 (7)	0.0589 (8)	−0.0043 (5)	0.0118 (6)	0.0042 (6)
C13	0.0379 (7)	0.0620 (9)	0.0686 (9)	−0.0139 (6)	0.0062 (6)	−0.0086 (7)
C14	0.0383 (7)	0.0537 (8)	0.0558 (7)	−0.0093 (6)	0.0009 (6)	−0.0077 (6)
C15	0.0331 (6)	0.0359 (6)	0.0443 (6)	−0.0015 (5)	0.0004 (5)	−0.0009 (5)
C16	0.0343 (6)	0.0356 (6)	0.0409 (6)	−0.0012 (4)	−0.0012 (5)	−0.0016 (5)
C17	0.0472 (9)	0.0626 (10)	0.0781 (11)	−0.0123 (7)	0.0114 (7)	−0.0048 (8)
C18	0.0496 (8)	0.0590 (9)	0.0450 (7)	−0.0091 (6)	0.0049 (6)	−0.0127 (6)
C19	0.0458 (8)	0.0706 (10)	0.0714 (10)	0.0002 (7)	0.0205 (7)	0.0012 (8)
C20	0.0619 (10)	0.0536 (9)	0.0931 (12)	−0.0001 (8)	0.0121 (9)	0.0182 (9)

Geometric parameters (Å, º) top

O1—C11	1.3693 (15)	C10—C18	1.5059 (17)
O1—C12	1.4625 (17)	C11—C15	1.3977 (17)
O2—C5	1.3741 (18)	C12—C13	1.497 (2)
O2—C17	1.410 (2)	C12—C19	1.517 (2)
N1—C16	1.3830 (16)	C12—C20	1.518 (2)
N1—C2	1.3859 (18)	C13—C14	1.323 (2)
N1—H1	0.872 (18)	C13—H13	0.9300
C2—C3	1.3911 (18)	C14—C15	1.4535 (19)
C2—C7	1.4050 (17)	C14—H14	0.9300
C3—C4	1.372 (2)	C15—C16	1.3945 (18)
C3—H3	0.9300	C17—H17A	0.9600
C4—C5	1.397 (2)	C17—H17B	0.9600
C4—H4	0.9300	C17—H17C	0.9600
C5—C6	1.3838 (18)	C18—H18A	0.9600
C6—C7	1.3920 (19)	C18—H18B	0.9600
C6—H6	0.9300	C18—H18C	0.9600
C7—C8	1.4463 (17)	C19—H19A	0.9600
C8—C9	1.3975 (16)	C19—H19B	0.9600
C8—C16	1.4075 (18)	C19—H19C	0.9600
C9—C10	1.3856 (17)	C20—H20A	0.9600
C9—H9	0.9300	C20—H20B	0.9600
C10—C11	1.4102 (18)	C20—H20C	0.9600

C11—O1—C12	118.95 (10)	C13—C12—C20	109.71 (14)
C5—O2—C17	118.11 (12)	C19—C12—C20	111.18 (13)
C16—N1—C2	108.60 (10)	C14—C13—C12	121.68 (13)
C16—N1—H1	126.3 (11)	C14—C13—H13	119.2
C2—N1—H1	124.4 (11)	C12—C13—H13	119.2
N1—C2—C3	129.69 (12)	C13—C14—C15	119.48 (13)
N1—C2—C7	109.20 (11)	C13—C14—H14	120.3
C3—C2—C7	121.11 (12)	C15—C14—H14	120.3
C4—C3—C2	117.87 (12)	C16—C15—C11	116.73 (11)
C4—C3—H3	121.1	C16—C15—C14	124.66 (12)
C2—C3—H3	121.1	C11—C15—C14	118.49 (11)
C3—C4—C5	121.62 (12)	N1—C16—C15	129.19 (11)
C3—C4—H4	119.2	N1—C16—C8	109.03 (11)
C5—C4—H4	119.2	C15—C16—C8	121.78 (11)
O2—C5—C6	124.51 (13)	O2—C17—H17A	109.5
O2—C5—C4	114.60 (12)	O2—C17—H17B	109.5
C6—C5—C4	120.87 (13)	H17A—C17—H17B	109.5
C5—C6—C7	118.19 (12)	O2—C17—H17C	109.5
C5—C6—H6	120.9	H17A—C17—H17C	109.5
C7—C6—H6	120.9	H17B—C17—H17C	109.5
C6—C7—C2	120.34 (12)	C10—C18—H18A	109.5
C6—C7—C8	133.19 (11)	C10—C18—H18B	109.5
C2—C7—C8	106.47 (11)	H18A—C18—H18B	109.5
C9—C8—C16	119.37 (11)	C10—C18—H18C	109.5
C9—C8—C7	133.94 (11)	H18A—C18—H18C	109.5
C16—C8—C7	106.68 (10)	H18B—C18—H18C	109.5
C10—C9—C8	120.78 (11)	C12—C19—H19A	109.5
C10—C9—H9	119.6	C12—C19—H19B	109.5
C8—C9—H9	119.6	H19A—C19—H19B	109.5
C9—C10—C11	118.11 (11)	C12—C19—H19C	109.5
C9—C10—C18	121.38 (11)	H19A—C19—H19C	109.5
C11—C10—C18	120.51 (11)	H19B—C19—H19C	109.5
O1—C11—C15	120.52 (11)	C12—C20—H20A	109.5
O1—C11—C10	116.22 (11)	C12—C20—H20B	109.5
C15—C11—C10	123.10 (11)	H20A—C20—H20B	109.5
O1—C12—C13	110.56 (11)	C12—C20—H20C	109.5
O1—C12—C19	104.16 (12)	H20A—C20—H20C	109.5
C13—C12—C19	112.32 (13)	H20B—C20—H20C	109.5
O1—C12—C20	108.74 (12)

C16—N1—C2—C3	−179.35 (13)	C9—C10—C11—O1	178.11 (11)
C16—N1—C2—C7	1.02 (15)	C18—C10—C11—O1	−1.39 (17)
N1—C2—C3—C4	179.97 (14)	C9—C10—C11—C15	2.60 (19)
C7—C2—C3—C4	−0.4 (2)	C18—C10—C11—C15	−176.90 (12)
C2—C3—C4—C5	0.0 (2)	C11—O1—C12—C13	36.86 (16)
C17—O2—C5—C6	19.3 (2)	C11—O1—C12—C19	157.72 (12)
C17—O2—C5—C4	−162.32 (14)	C11—O1—C12—C20	−83.65 (15)
C3—C4—C5—O2	−177.91 (13)	O1—C12—C13—C14	−29.5 (2)
C3—C4—C5—C6	0.5 (2)	C19—C12—C13—C14	−145.39 (16)
O2—C5—C6—C7	177.72 (13)	C20—C12—C13—C14	90.42 (18)
C4—C5—C6—C7	−0.5 (2)	C12—C13—C14—C15	6.7 (2)
C5—C6—C7—C2	0.09 (19)	O1—C11—C15—C16	−179.54 (10)
C5—C6—C7—C8	−179.29 (13)	C10—C11—C15—C16	−4.22 (18)
N1—C2—C7—C6	−179.94 (11)	O1—C11—C15—C14	−3.37 (18)
C3—C2—C7—C6	0.4 (2)	C10—C11—C15—C14	171.96 (12)
N1—C2—C7—C8	−0.40 (14)	C13—C14—C15—C16	−172.97 (14)
C3—C2—C7—C8	179.92 (12)	C13—C14—C15—C11	11.2 (2)
C6—C7—C8—C9	0.6 (2)	C2—N1—C16—C15	178.26 (13)
C2—C7—C8—C9	−178.84 (13)	C2—N1—C16—C8	−1.24 (14)
C6—C7—C8—C16	179.10 (13)	C11—C15—C16—N1	−176.68 (12)
C2—C7—C8—C16	−0.34 (13)	C14—C15—C16—N1	7.4 (2)
C16—C8—C9—C10	−1.93 (18)	C11—C15—C16—C8	2.77 (18)
C7—C8—C9—C10	176.42 (12)	C14—C15—C16—C8	−173.14 (12)
C8—C9—C10—C11	0.59 (18)	C9—C8—C16—N1	179.73 (11)
C8—C9—C10—C18	−179.91 (12)	C7—C8—C16—N1	0.97 (14)
C12—O1—C11—C15	−22.17 (17)	C9—C8—C16—C15	0.18 (18)
C12—O1—C11—C10	162.20 (11)	C7—C8—C16—C15	−178.58 (11)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1/C2/C7/C8/C16 ring and Cg4 is the centroid of the C8–C11/C15/C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.93	2.54	3.333 (2)	143
N1—H1···Cg4ⁱⁱ	0.872 (18)	2.744 (17)	3.528 (2)	149.7 (14)
C17—H17C···Cg1ⁱⁱⁱ	0.96	3.08	3.489 (3)	107
C17—H17C···Cg4ⁱⁱⁱ	0.96	3.00	3.514 (3)	115

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉NO₂
M_r	293.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.290 (5), 8.693 (5), 21.326 (5)
β (°)	90.742 (5)
V (Å³)	1536.7 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.17 × 0.16

Data collection
Diffractometer	Bruker SMART APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.984, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	14325, 3803, 3050
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.137, 1.05
No. of reflections	3803
No. of parameters	207
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.22

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1/C2/C7/C8/C16 ring and Cg4 is the centroid of the C8–C11/C15/C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.93	2.54	3.333 (2)	143.0
N1—H1···Cg4ⁱⁱ	0.872 (18)	2.744 (17)	3.528 (2)	149.7 (14)
C17—H17C···Cg1ⁱⁱⁱ	0.9600	3.0797	3.489 (3)	107.37
C17—H17C···Cg4ⁱⁱⁱ	0.9600	3.0002	3.514 (3)	114.87

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

Acknowledgements

The authors wish to thank the TBI Consultancy, University of Madras, Chennai, for the data collection.

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
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 (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chowdhury, B. K., Jha, S., Bhattacharya, P. & Mukherjee, J. (2001). Indian J. Chem. Sect. B, 40, 490–494. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Fiebi, M., Pezzuto, J. M., Soejarto, D. D. & Kinghorn, A. D. (1985). Phytochemistry, 24, 3041–3043. Google Scholar
Ito, C. (2000). Nat. Med. 54, 117–122. CAS Google Scholar
Kong, Y. C., Ng, K. H., But, P. P. H., li, Q., Yu, S. X., Zhang, H. T., Cheng, K. F., Soejarto, D. D., Kan, W. S. & Waterman, P. G. (1986). J. Ethanopharmacol. 15,195–200. CAS Google Scholar
Nardelli, M. (1983). Acta Cryst. C39, 1141–1142. CrossRef CAS Web of Science IUCr Journals Google Scholar
Ramsewak, R. S., Nair, M. G., Strasburg, G. M., DeWirr, D. L. & Nitiss, J. L. (1999). J. Agric. Food Chem. 47, 444–447. Web of Science CrossRef PubMed CAS 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

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Volume 66| Part 7| July 2010| Page o1581

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