rac-4a,10b-cis,10b,5c-trans-5-(7-Methyl-2-oxo-2H-chromen-4-yl)-3,4,4a,5,6,10b-hexa­hydro-2H-pyrano[3,2-c]quinoline

Kayalvizhi, M.; Vasuki, G.; Samant, S.D.; Sanap, K.K.

doi:10.1107/S1600536813001876

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o280

doi:10.1107/S1600536813001876

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rac-4a,10b-cis,10b,5c-trans-5-(7-Methyl-2-oxo-2H-chromen-4-yl)-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline

M. Kayalvizhi,^a G. Vasuki,^a ^* Shriniwas D. Samant ^b and Kailas K. Sanap ^b

^aDepartment of Physics, Kunthavai Naachiar Government Arts College (W) (Autonomous), Thanjavur-7, India, and ^bDepartment of Chemistry, Institute of Chemical Technology, N.M. Parekh Road, Matunga, Mumbai 400 019, India
^*Correspondence e-mail: vasuki.arasi@yahoo.com

(Received 17 December 2012; accepted 18 January 2013; online 23 January 2013)

In the racemic title compound, C₂₂H₂₁NO₃, the nitrogen-containing ring of the pyranoquinoline moiety adopts a slightly distorted half-chair conformation and the oxygen-containing ring adopts a slightly distorted chair conformation. The benzene rings make a dihedral angle of 84.97 (8)°. In the crystal, weak C—H⋯O interactions link the molecules into chains extending along the a-axis direction.

Related literature

For general background and related coumarin compounds, see: Aazam et al. (2006 ); Chinnakali et al. (2009 ); Du et al. (2010 ); Pereira Silva et al. (2010 ). For ring conformational analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₂H₂₁NO₃
M_r = 347.40
Triclinic, $[P \overline 1]$
a = 7.7529 (4) Å
b = 11.2790 (7) Å
c = 11.7563 (11) Å
α = 117.232 (3)°
β = 98.475 (3)°
γ = 101.301 (2)°
V = 862.60 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.20 × 0.15 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker 1999 ) T_min = 0.984, T_max = 0.987
18945 measured reflections
5009 independent reflections
3544 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.177
S = 1.03
5009 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O1ⁱ	0.97	2.59	3.307 (3)	131
C20—H20⋯O2ⁱⁱ	0.93	2.40	3.275 (2)	157
Symmetry codes: (i) -x+2, -y+2, -z; (ii) x+1, y, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (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, 2012 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813001876/zs2247sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813001876/zs2247Isup2.hkl

checkCIF report

Comment top

Coumarin is the simplest member of the group of oxygen heterocyclic compounds called benzo-2-pyrones. Coumarins are an important class of compound due to their presence in natural products as well as their medicinal applications, e.g. as anti-inflammatory, anti-viral, antioxidant, antibacterial, antifungal, anti-HIV and as anti-carcinogenic agents (Pereira Silva et al., 2010). Coumarin and its derivatives also have applications as fluorescent dyes for synthetic fibres and daylight fluorescent pigments (Aazam et al., 2006) and as cosmetics, optical brightening agents and laser dyes (Pereira Silva et al., 2010). The synthesis of pyranoquinoline derivatives has been the focus of great interest, because it was reported that these possess a broad spectrum of biological properties such as psychotropic activity and anti-allergenic activity and they are also used for the treatment of proliferative diseases, such as cancer (Du et al., 2010). Compounds containing pyranoquinolone motifs also exhibit antiproliferative and antitubulin activities and it includes antibacterial and antifungal activities. Some of the pyranoquinoline derivatives have been found to block acetylcholinesterase and cell calcium signals, and cause neuroprotection against calcium overload and free radicals (Chinnakali et al., 2009).

We report herein the crystal structure of the racemic title compound, a pyranoquinoline-substituted methyl coumarin derivative, C₂₂H₂₁NO₃ (Fig. 1). The dihedral angle between the phenyl rings of the coumarin molecule and the pyranoquinoline moiety is 84.97 (8)° . The C15 atom of the carbonyl group has a distorted trigonal geometry with O2—C15—O1 [117.36 (14)°] and O2—C15—C14 [125.26 (16)°], deviating significantly from the ideal sp² value of 120°, which is consistent with the values observed in a related structure (Pereira Silva et al., 2010). In the crystal, weak intermolecular C20—H···O2ⁱⁱ hydrogen bonds together with C12—H···O1ⁱ hydrogen bonds between inversion-related molecules (Table 1), give one-dimensional chain structures which extend along the a axis (Fig. 2). Present also in the crystal packing are C5—H···π ring interactions [minimum C···Cg separation, 3.910 (3) Å] (for symmetry codes, see Table 1). The substituent ring defined by (N1, C1, C6–C9) adopts a slightly distorted half-chair conformation with Q = 0.4852 (18) Å, θ = 48.0 (2)° and ϕ = 259.3 (3)° while the ring defined by (O3, C7–C12) adopts a slightly distorted chair conformation with Q = 0.548 (2) Å, θ = 2.8 (2)° and ϕ = 300 (5)° (Cremer & Pople, 1975).

Related literature top

For general background and related coumarin compounds, see: Aazam et al. (2006); Chinnakali et al. (2009); Du et al. (2010); Pereira Silva et al. (2010). For ring conformational analysis, see: Cremer & Pople (1975).

Experimental top

7-Methylcoumarin-4-azadiene (0.263 g, 1 mmol) and ZnCl₂ (0.136 g, 1 mmol) were stirred in dichloroethane (5 ml) for 15 minutes and dihydropyran (0.252 g, 3 mmol) was added slowly at room temperature. The solution was heated till complete consumption of the coumarin reagent. The solution was cooled to room temperature, quenched with water and the product was extracted with chloroform. The extract was dried over anhydrous Na₂SO₄ and the solvent evaporated to obtain a sticky mass which was purified by column chromatography on silica gel using chloroform.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (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, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound showing atom numbering, with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A view of the crystal packing of the title compound looking down the a axis, showing C—H···O interactions as dashed lines.

rac-4a,10-cis,10b,5c-trans-5-(7-Methyl-2-oxo-2H-chromen-4-yl)-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline top

Crystal data top

C₂₂H₂₁NO₃	Z = 2
M_r = 347.40	F(000) = 368
Triclinic, P1	D_x = 1.338 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7529 (4) Å	Cell parameters from 6950 reflections
b = 11.2790 (7) Å	θ = 2.1–30.2°
c = 11.7563 (11) Å	µ = 0.09 mm⁻¹
α = 117.232 (3)°	T = 296 K
β = 98.475 (3)°	Block, colourless
γ = 101.301 (2)°	0.20 × 0.15 × 0.15 mm
V = 862.60 (11) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	5009 independent reflections
Radiation source: fine-focus sealed tube	3544 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω and ϕ scan	θ_max = 30.2°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker 1999)	h = −10→10
T_min = 0.984, T_max = 0.987	k = −15→15
18945 measured reflections	l = −16→16

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.177	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0832P)² + 0.3474P] where P = (F_o² + 2F_c²)/3
5009 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₂H₂₁NO₃	γ = 101.301 (2)°
M_r = 347.40	V = 862.60 (11) Å³
Triclinic, P1	Z = 2
a = 7.7529 (4) Å	Mo Kα radiation
b = 11.2790 (7) Å	µ = 0.09 mm⁻¹
c = 11.7563 (11) Å	T = 296 K
α = 117.232 (3)°	0.20 × 0.15 × 0.15 mm
β = 98.475 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	5009 independent reflections
Absorption correction: multi-scan (SADABS; Bruker 1999)	3544 reflections with I > 2σ(I)
T_min = 0.984, T_max = 0.987	R_int = 0.030
18945 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.177	H-atom parameters constrained
S = 1.03	Δρ_max = 0.41 e Å⁻³
5009 reflections	Δρ_min = −0.27 e Å⁻³
235 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
O1	0.69639 (15)	0.63713 (13)	0.02296 (11)	0.0385 (3)
C13	0.9273 (2)	0.64223 (15)	−0.13810 (14)	0.0305 (3)
C21	1.0013 (2)	0.66621 (15)	−0.00600 (14)	0.0306 (3)
N1	0.95359 (19)	0.59869 (13)	−0.35976 (12)	0.0343 (3)
H1	0.9425	0.5149	−0.4199	0.041*
C16	0.8806 (2)	0.66458 (16)	0.07070 (15)	0.0321 (3)
C14	0.7463 (2)	0.61512 (17)	−0.18120 (16)	0.0363 (3)
H14	0.6982	0.5978	−0.2665	0.044*
C9	1.0532 (2)	0.65038 (16)	−0.22402 (14)	0.0320 (3)
H9	1.1325	0.5922	−0.2253	0.038*
C1	0.8757 (2)	0.68235 (16)	−0.39430 (14)	0.0315 (3)
C17	0.9383 (2)	0.69114 (17)	0.19930 (16)	0.0377 (3)
H17	0.8538	0.6898	0.2476	0.045*
C18	1.1206 (2)	0.71958 (17)	0.25613 (16)	0.0375 (3)
C19	1.2429 (2)	0.71608 (18)	0.17925 (17)	0.0394 (4)
H19	1.3659	0.7322	0.2154	0.047*
C20	1.1850 (2)	0.68931 (18)	0.05130 (16)	0.0372 (3)
H20	1.2691	0.6865	0.0020	0.045*
O3	1.16897 (19)	1.03131 (13)	−0.12889 (13)	0.0526 (4)
C8	1.1758 (2)	0.80019 (17)	−0.16807 (15)	0.0363 (3)
H8	1.2389	0.8366	−0.0748	0.044*
O2	0.45952 (18)	0.58805 (17)	−0.13623 (15)	0.0564 (4)
C15	0.6228 (2)	0.61153 (18)	−0.10156 (17)	0.0377 (3)
C7	1.0589 (2)	0.89261 (16)	−0.17287 (16)	0.0384 (4)
H7	0.9858	0.9001	−0.1100	0.046*
C6	0.9262 (2)	0.82680 (16)	−0.30839 (16)	0.0359 (3)
C10	1.3203 (2)	0.8037 (2)	−0.24303 (18)	0.0419 (4)
H10A	1.4040	0.7555	−0.2280	0.050*
H10B	1.2614	0.7557	−0.3376	0.050*
C2	0.7472 (2)	0.62255 (19)	−0.51719 (17)	0.0415 (4)
H2	0.7121	0.5264	−0.5744	0.050*
C22	1.1856 (3)	0.7542 (2)	0.39765 (18)	0.0518 (5)
H22A	1.3155	0.7709	0.4209	0.078*
H22B	1.1263	0.6775	0.4072	0.078*
H22C	1.1566	0.8365	0.4553	0.078*
C12	1.2970 (3)	1.03446 (19)	−0.2043 (2)	0.0537 (5)
H12A	1.3662	1.1307	−0.1712	0.064*
H12B	1.2311	0.9952	−0.2965	0.064*
C5	0.8472 (3)	0.9065 (2)	−0.3492 (2)	0.0514 (5)
H5	0.8796	1.0026	−0.2928	0.062*
C4	0.7226 (3)	0.8466 (3)	−0.4707 (3)	0.0616 (6)
H4	0.6724	0.9019	−0.4964	0.074*
C3	0.6725 (3)	0.7046 (2)	−0.5542 (2)	0.0542 (5)
H3	0.5874	0.6638	−0.6362	0.065*
C11	1.4262 (3)	0.9538 (2)	−0.1964 (2)	0.0541 (5)
H11A	1.5002	0.9976	−0.1055	0.065*
H11B	1.5073	0.9547	−0.2517	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0341 (6)	0.0493 (7)	0.0405 (6)	0.0154 (5)	0.0186 (5)	0.0257 (5)
C13	0.0329 (7)	0.0325 (7)	0.0300 (7)	0.0116 (6)	0.0133 (6)	0.0168 (6)
C21	0.0330 (7)	0.0326 (7)	0.0307 (7)	0.0112 (6)	0.0127 (6)	0.0179 (6)
N1	0.0461 (8)	0.0300 (6)	0.0254 (6)	0.0145 (5)	0.0118 (5)	0.0110 (5)
C16	0.0333 (8)	0.0330 (7)	0.0347 (7)	0.0117 (6)	0.0140 (6)	0.0188 (6)
C14	0.0354 (8)	0.0440 (9)	0.0344 (8)	0.0131 (6)	0.0123 (6)	0.0221 (7)
C9	0.0336 (8)	0.0388 (8)	0.0285 (7)	0.0134 (6)	0.0134 (6)	0.0185 (6)
C1	0.0342 (8)	0.0345 (7)	0.0290 (7)	0.0109 (6)	0.0135 (6)	0.0166 (6)
C17	0.0450 (9)	0.0409 (8)	0.0358 (8)	0.0145 (7)	0.0202 (7)	0.0227 (7)
C18	0.0469 (9)	0.0359 (8)	0.0328 (7)	0.0104 (7)	0.0119 (6)	0.0202 (6)
C19	0.0349 (8)	0.0485 (9)	0.0399 (8)	0.0119 (7)	0.0084 (6)	0.0270 (8)
C20	0.0350 (8)	0.0480 (9)	0.0387 (8)	0.0145 (7)	0.0162 (6)	0.0270 (7)
O3	0.0595 (8)	0.0312 (6)	0.0472 (7)	0.0018 (5)	0.0232 (6)	0.0061 (5)
C8	0.0350 (8)	0.0436 (9)	0.0263 (7)	0.0046 (6)	0.0087 (6)	0.0170 (6)
O2	0.0334 (7)	0.0876 (11)	0.0619 (9)	0.0234 (7)	0.0187 (6)	0.0447 (8)
C15	0.0333 (8)	0.0444 (9)	0.0429 (8)	0.0150 (6)	0.0142 (6)	0.0253 (7)
C7	0.0426 (9)	0.0307 (7)	0.0318 (7)	0.0051 (6)	0.0161 (6)	0.0082 (6)
C6	0.0373 (8)	0.0332 (8)	0.0372 (8)	0.0117 (6)	0.0148 (6)	0.0158 (6)
C10	0.0372 (9)	0.0538 (10)	0.0450 (9)	0.0143 (7)	0.0179 (7)	0.0307 (8)
C2	0.0387 (9)	0.0463 (9)	0.0346 (8)	0.0095 (7)	0.0088 (7)	0.0179 (7)
C22	0.0595 (12)	0.0614 (12)	0.0362 (9)	0.0124 (9)	0.0112 (8)	0.0287 (9)
C12	0.0603 (12)	0.0368 (9)	0.0536 (11)	0.0000 (8)	0.0229 (9)	0.0179 (8)
C5	0.0519 (11)	0.0411 (9)	0.0682 (13)	0.0204 (8)	0.0198 (9)	0.0294 (9)
C4	0.0565 (13)	0.0700 (14)	0.0808 (15)	0.0291 (11)	0.0165 (11)	0.0524 (13)
C3	0.0425 (10)	0.0737 (14)	0.0523 (11)	0.0169 (9)	0.0072 (8)	0.0381 (11)
C11	0.0416 (10)	0.0625 (12)	0.0491 (10)	−0.0022 (8)	0.0143 (8)	0.0271 (9)

Geometric parameters (Å, º) top

O1—C15	1.362 (2)	C8—C7	1.523 (2)
O1—C16	1.3720 (19)	C8—C10	1.529 (2)
C13—C14	1.342 (2)	C8—H8	0.9800
C13—C21	1.451 (2)	O2—C15	1.207 (2)
C13—C9	1.5237 (19)	C7—C6	1.511 (2)
C21—C16	1.3948 (19)	C7—H7	0.9800
C21—C20	1.401 (2)	C6—C5	1.391 (2)
N1—C1	1.386 (2)	C10—C11	1.522 (3)
N1—C9	1.4463 (19)	C10—H10A	0.9700
N1—H1	0.8600	C10—H10B	0.9700
C16—C17	1.382 (2)	C2—C3	1.373 (3)
C14—C15	1.442 (2)	C2—H2	0.9300
C14—H14	0.9300	C22—H22A	0.9600
C9—C8	1.536 (2)	C22—H22B	0.9600
C9—H9	0.9800	C22—H22C	0.9600
C1—C2	1.398 (2)	C12—C11	1.499 (3)
C1—C6	1.398 (2)	C12—H12A	0.9700
C17—C18	1.377 (2)	C12—H12B	0.9700
C17—H17	0.9300	C5—C4	1.373 (3)
C18—C19	1.397 (2)	C5—H5	0.9300
C18—C22	1.502 (2)	C4—C3	1.372 (3)
C19—C20	1.374 (2)	C4—H4	0.9300
C19—H19	0.9300	C3—H3	0.9300
C20—H20	0.9300	C11—H11A	0.9700
O3—C12	1.431 (2)	C11—H11B	0.9700
O3—C7	1.4316 (19)

C15—O1—C16	121.40 (12)	O1—C15—C14	117.37 (14)
C14—C13—C21	118.25 (13)	O3—C7—C6	112.52 (14)
C14—C13—C9	121.18 (13)	O3—C7—C8	111.57 (14)
C21—C13—C9	120.56 (13)	C6—C7—C8	111.58 (12)
C16—C21—C20	116.62 (13)	O3—C7—H7	106.9
C16—C21—C13	117.98 (13)	C6—C7—H7	106.9
C20—C21—C13	125.39 (13)	C8—C7—H7	106.9
C1—N1—C9	120.93 (12)	C5—C6—C1	118.48 (16)
C1—N1—H1	119.5	C5—C6—C7	121.39 (15)
C9—N1—H1	119.5	C1—C6—C7	120.10 (14)
O1—C16—C17	115.72 (13)	C11—C10—C8	110.52 (15)
O1—C16—C21	121.83 (13)	C11—C10—H10A	109.5
C17—C16—C21	122.45 (15)	C8—C10—H10A	109.5
C13—C14—C15	123.12 (14)	C11—C10—H10B	109.5
C13—C14—H14	118.4	C8—C10—H10B	109.5
C15—C14—H14	118.4	H10A—C10—H10B	108.1
N1—C9—C13	112.47 (12)	C3—C2—C1	120.53 (17)
N1—C9—C8	108.27 (12)	C3—C2—H2	119.7
C13—C9—C8	112.04 (12)	C1—C2—H2	119.7
N1—C9—H9	108.0	C18—C22—H22A	109.5
C13—C9—H9	108.0	C18—C22—H22B	109.5
C8—C9—H9	108.0	H22A—C22—H22B	109.5
N1—C1—C2	119.91 (14)	C18—C22—H22C	109.5
N1—C1—C6	120.76 (14)	H22A—C22—H22C	109.5
C2—C1—C6	119.33 (15)	H22B—C22—H22C	109.5
C18—C17—C16	120.12 (14)	O3—C12—C11	111.81 (16)
C18—C17—H17	119.9	O3—C12—H12A	109.3
C16—C17—H17	119.9	C11—C12—H12A	109.3
C17—C18—C19	118.40 (14)	O3—C12—H12B	109.3
C17—C18—C22	120.50 (15)	C11—C12—H12B	109.3
C19—C18—C22	121.10 (16)	H12A—C12—H12B	107.9
C20—C19—C18	121.31 (15)	C4—C5—C6	121.58 (18)
C20—C19—H19	119.3	C4—C5—H5	119.2
C18—C19—H19	119.3	C6—C5—H5	119.2
C19—C20—C21	120.98 (14)	C3—C4—C5	119.68 (18)
C19—C20—H20	119.5	C3—C4—H4	120.2
C21—C20—H20	119.5	C5—C4—H4	120.2
C12—O3—C7	112.87 (13)	C4—C3—C2	120.39 (18)
C7—C8—C10	110.95 (13)	C4—C3—H3	119.8
C7—C8—C9	109.85 (13)	C2—C3—H3	119.8
C10—C8—C9	111.42 (13)	C12—C11—C10	110.22 (15)
C7—C8—H8	108.2	C12—C11—H11A	109.6
C10—C8—H8	108.2	C10—C11—H11A	109.6
C9—C8—H8	108.2	C12—C11—H11B	109.6
O2—C15—O1	117.36 (14)	C10—C11—H11B	109.6
O2—C15—C14	125.26 (16)	H11A—C11—H11B	108.1

C14—C13—C21—C16	−2.2 (2)	C13—C9—C8—C10	171.57 (13)
C9—C13—C21—C16	176.72 (13)	C16—O1—C15—O2	179.89 (15)
C14—C13—C21—C20	176.89 (15)	C16—O1—C15—C14	−0.3 (2)
C9—C13—C21—C20	−4.2 (2)	C13—C14—C15—O2	179.75 (18)
C15—O1—C16—C17	178.94 (14)	C13—C14—C15—O1	0.0 (2)
C15—O1—C16—C21	−0.7 (2)	C12—O3—C7—C6	−68.9 (2)
C20—C21—C16—O1	−177.22 (14)	C12—O3—C7—C8	57.39 (19)
C13—C21—C16—O1	2.0 (2)	C10—C8—C7—O3	−52.89 (17)
C20—C21—C16—C17	3.2 (2)	C9—C8—C7—O3	−176.54 (12)
C13—C21—C16—C17	−177.65 (14)	C10—C8—C7—C6	73.92 (16)
C21—C13—C14—C15	1.3 (2)	C9—C8—C7—C6	−49.72 (16)
C9—C13—C14—C15	−177.63 (14)	N1—C1—C6—C5	178.45 (15)
C1—N1—C9—C13	81.22 (17)	C2—C1—C6—C5	−0.5 (2)
C1—N1—C9—C8	−43.13 (18)	N1—C1—C6—C7	−3.5 (2)
C14—C13—C9—N1	−11.8 (2)	C2—C1—C6—C7	177.48 (14)
C21—C13—C9—N1	169.30 (13)	O3—C7—C6—C5	−33.6 (2)
C14—C13—C9—C8	110.44 (17)	C8—C7—C6—C5	−159.93 (15)
C21—C13—C9—C8	−68.46 (18)	O3—C7—C6—C1	148.42 (14)
C9—N1—C1—C2	−165.72 (14)	C8—C7—C6—C1	22.1 (2)
C9—N1—C1—C6	15.3 (2)	C7—C8—C10—C11	51.00 (19)
O1—C16—C17—C18	179.88 (14)	C9—C8—C10—C11	173.74 (14)
C21—C16—C17—C18	−0.5 (2)	N1—C1—C2—C3	−178.30 (15)
C16—C17—C18—C19	−2.1 (2)	C6—C1—C2—C3	0.7 (2)
C16—C17—C18—C22	177.53 (16)	C7—O3—C12—C11	−59.8 (2)
C17—C18—C19—C20	2.0 (3)	C1—C6—C5—C4	−0.1 (3)
C22—C18—C19—C20	−177.66 (16)	C7—C6—C5—C4	−178.11 (18)
C18—C19—C20—C21	0.8 (3)	C6—C5—C4—C3	0.7 (3)
C16—C21—C20—C19	−3.3 (2)	C5—C4—C3—C2	−0.5 (3)
C13—C21—C20—C19	177.62 (15)	C1—C2—C3—C4	−0.2 (3)
N1—C9—C8—C7	59.54 (15)	O3—C12—C11—C10	56.8 (2)
C13—C9—C8—C7	−65.06 (16)	C8—C10—C11—C12	−52.7 (2)
N1—C9—C8—C10	−63.82 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···N1	0.97	2.58	2.947 (2)	103
C12—H12A···O1ⁱ	0.97	2.59	3.307 (3)	131
C14—H14···N1	0.93	2.40	2.789 (2)	105
C20—H20···O2ⁱⁱ	0.93	2.40	3.275 (2)	157
C5—H5···Cg5ⁱⁱⁱ	0.93	2.98	3.910 (3)	173

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

Experimental details

Crystal data
Chemical formula	C₂₂H₂₁NO₃
M_r	347.40
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.7529 (4), 11.2790 (7), 11.7563 (11)
α, β, γ (°)	117.232 (3), 98.475 (3), 101.301 (2)
V (Å³)	862.60 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.15 × 0.15

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker 1999)
T_min, T_max	0.984, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	18945, 5009, 3544
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.707

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.177, 1.03
No. of reflections	5009
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.27

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O1ⁱ	0.97	2.59	3.307 (3)	131
C20—H20···O2ⁱⁱ	0.93	2.40	3.275 (2)	157

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

Acknowledgements

The authors thank the Sophisticated Analytical Instrument Facility, IIT-Madras, Chennai, for the data collection.

References

Aazam, E. S., Fawazy, A. & Hitchcock, P. B. (2006). Acta Cryst. E62, o4285–o4287. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (1999). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2 SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chinnakali, K., Sudha, D., Jayagobi, M., Raghunathan, R. & Fun, H.-K. (2009). Acta Cryst. E65, o2099–o2100. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Du, B.-X., Zhou, J., Li, Y.-L. & Wang, X.-S. (2010). Acta Cryst. E66, o1622. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Pereira Silva, P. S., Parveen, M., Khanam, Z., Ali, A. & Ramos Silva, M. (2010). Acta Cryst. E66, o988. Web of Science 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

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Volume 69| Part 2| February 2013| Page o280

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

rac-4a,10b-cis,10b,5c-trans-5-(7-Methyl-2-oxo-2H-chromen-4-yl)-3,4,4a,5,6,10b-hexa­hydro-2H-pyrano[3,2-c]quinoline

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

rac-4a,10b-cis,10b,5c-trans-5-(7-Methyl-2-oxo-2H-chromen-4-yl)-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline