Literature DB >> 23424553

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

M Kayalvizhi1, G Vasuki, Shriniwas D Samant, Kailas K Sanap.   

Abstract

In the racemic title compound, C(22)H(21)NO(3), the nitro-gen-containing ring of the pyran-oquinoline 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 inter-actions link the mol-ecules into chains extending along the a-axis direction.

Entities:  

Year:  2013        PMID： 23424553      PMCID： PMC3569807          DOI： 10.1107/S1600536813001876

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


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 = 347.40 Triclinic, 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[F 2 > 2σ(F 2)] = 0.055 wR(F 2) = 0.177 S = 1.03 5009 reflections 235 parameters H-atom parameters constrained Δρmax = 0.41 e Å−3 Δρmin = −0.27 e Å−3 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 ▶). Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813001876/zs2247sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001876/zs2247Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C22H21NO3Z = 2
Mr = 347.40F(000) = 368
Triclinic, P1Dx = 1.338 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.7529 (4) ÅCell parameters from 6950 reflections
b = 11.2790 (7) Åθ = 2.1–30.2°
c = 11.7563 (11) ŵ = 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
Bruker Kappa APEXII CCD diffractometer5009 independent reflections
Radiation source: fine-focus sealed tube3544 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
ω and φ scanθmax = 30.2°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker 1999)h = −10→10
Tmin = 0.984, Tmax = 0.987k = −15→15
18945 measured reflectionsl = −16→16
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.177H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0832P)2 + 0.3474P] where P = (Fo2 + 2Fc2)/3
5009 reflections(Δ/σ)max = 0.001
235 parametersΔρmax = 0.41 e Å−3
0 restraintsΔρmin = −0.27 e Å−3
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.
xyzUiso*/Ueq
O10.69639 (15)0.63713 (13)0.02296 (11)0.0385 (3)
C130.9273 (2)0.64223 (15)−0.13810 (14)0.0305 (3)
C211.0013 (2)0.66621 (15)−0.00600 (14)0.0306 (3)
N10.95359 (19)0.59869 (13)−0.35976 (12)0.0343 (3)
H10.94250.5149−0.41990.041*
C160.8806 (2)0.66458 (16)0.07070 (15)0.0321 (3)
C140.7463 (2)0.61512 (17)−0.18120 (16)0.0363 (3)
H140.69820.5978−0.26650.044*
C91.0532 (2)0.65038 (16)−0.22402 (14)0.0320 (3)
H91.13250.5922−0.22530.038*
C10.8757 (2)0.68235 (16)−0.39430 (14)0.0315 (3)
C170.9383 (2)0.69114 (17)0.19930 (16)0.0377 (3)
H170.85380.68980.24760.045*
C181.1206 (2)0.71958 (17)0.25613 (16)0.0375 (3)
C191.2429 (2)0.71608 (18)0.17925 (17)0.0394 (4)
H191.36590.73220.21540.047*
C201.1850 (2)0.68931 (18)0.05130 (16)0.0372 (3)
H201.26910.68650.00200.045*
O31.16897 (19)1.03131 (13)−0.12889 (13)0.0526 (4)
C81.1758 (2)0.80019 (17)−0.16807 (15)0.0363 (3)
H81.23890.8366−0.07480.044*
O20.45952 (18)0.58805 (17)−0.13623 (15)0.0564 (4)
C150.6228 (2)0.61153 (18)−0.10156 (17)0.0377 (3)
C71.0589 (2)0.89261 (16)−0.17287 (16)0.0384 (4)
H70.98580.9001−0.11000.046*
C60.9262 (2)0.82680 (16)−0.30839 (16)0.0359 (3)
C101.3203 (2)0.8037 (2)−0.24303 (18)0.0419 (4)
H10A1.40400.7555−0.22800.050*
H10B1.26140.7557−0.33760.050*
C20.7472 (2)0.62255 (19)−0.51719 (17)0.0415 (4)
H20.71210.5264−0.57440.050*
C221.1856 (3)0.7542 (2)0.39765 (18)0.0518 (5)
H22A1.31550.77090.42090.078*
H22B1.12630.67750.40720.078*
H22C1.15660.83650.45530.078*
C121.2970 (3)1.03446 (19)−0.2043 (2)0.0537 (5)
H12A1.36621.1307−0.17120.064*
H12B1.23110.9952−0.29650.064*
C50.8472 (3)0.9065 (2)−0.3492 (2)0.0514 (5)
H50.87961.0026−0.29280.062*
C40.7226 (3)0.8466 (3)−0.4707 (3)0.0616 (6)
H40.67240.9019−0.49640.074*
C30.6725 (3)0.7046 (2)−0.5542 (2)0.0542 (5)
H30.58740.6638−0.63620.065*
C111.4262 (3)0.9538 (2)−0.1964 (2)0.0541 (5)
H11A1.50020.9976−0.10550.065*
H11B1.50730.9547−0.25170.065*
U11U22U33U12U13U23
O10.0341 (6)0.0493 (7)0.0405 (6)0.0154 (5)0.0186 (5)0.0257 (5)
C130.0329 (7)0.0325 (7)0.0300 (7)0.0116 (6)0.0133 (6)0.0168 (6)
C210.0330 (7)0.0326 (7)0.0307 (7)0.0112 (6)0.0127 (6)0.0179 (6)
N10.0461 (8)0.0300 (6)0.0254 (6)0.0145 (5)0.0118 (5)0.0110 (5)
C160.0333 (8)0.0330 (7)0.0347 (7)0.0117 (6)0.0140 (6)0.0188 (6)
C140.0354 (8)0.0440 (9)0.0344 (8)0.0131 (6)0.0123 (6)0.0221 (7)
C90.0336 (8)0.0388 (8)0.0285 (7)0.0134 (6)0.0134 (6)0.0185 (6)
C10.0342 (8)0.0345 (7)0.0290 (7)0.0109 (6)0.0135 (6)0.0166 (6)
C170.0450 (9)0.0409 (8)0.0358 (8)0.0145 (7)0.0202 (7)0.0227 (7)
C180.0469 (9)0.0359 (8)0.0328 (7)0.0104 (7)0.0119 (6)0.0202 (6)
C190.0349 (8)0.0485 (9)0.0399 (8)0.0119 (7)0.0084 (6)0.0270 (8)
C200.0350 (8)0.0480 (9)0.0387 (8)0.0145 (7)0.0162 (6)0.0270 (7)
O30.0595 (8)0.0312 (6)0.0472 (7)0.0018 (5)0.0232 (6)0.0061 (5)
C80.0350 (8)0.0436 (9)0.0263 (7)0.0046 (6)0.0087 (6)0.0170 (6)
O20.0334 (7)0.0876 (11)0.0619 (9)0.0234 (7)0.0187 (6)0.0447 (8)
C150.0333 (8)0.0444 (9)0.0429 (8)0.0150 (6)0.0142 (6)0.0253 (7)
C70.0426 (9)0.0307 (7)0.0318 (7)0.0051 (6)0.0161 (6)0.0082 (6)
C60.0373 (8)0.0332 (8)0.0372 (8)0.0117 (6)0.0148 (6)0.0158 (6)
C100.0372 (9)0.0538 (10)0.0450 (9)0.0143 (7)0.0179 (7)0.0307 (8)
C20.0387 (9)0.0463 (9)0.0346 (8)0.0095 (7)0.0088 (7)0.0179 (7)
C220.0595 (12)0.0614 (12)0.0362 (9)0.0124 (9)0.0112 (8)0.0287 (9)
C120.0603 (12)0.0368 (9)0.0536 (11)0.0000 (8)0.0229 (9)0.0179 (8)
C50.0519 (11)0.0411 (9)0.0682 (13)0.0204 (8)0.0198 (9)0.0294 (9)
C40.0565 (13)0.0700 (14)0.0808 (15)0.0291 (11)0.0165 (11)0.0524 (13)
C30.0425 (10)0.0737 (14)0.0523 (11)0.0169 (9)0.0072 (8)0.0381 (11)
C110.0416 (10)0.0625 (12)0.0491 (10)−0.0022 (8)0.0143 (8)0.0271 (9)
O1—C151.362 (2)C8—C71.523 (2)
O1—C161.3720 (19)C8—C101.529 (2)
C13—C141.342 (2)C8—H80.9800
C13—C211.451 (2)O2—C151.207 (2)
C13—C91.5237 (19)C7—C61.511 (2)
C21—C161.3948 (19)C7—H70.9800
C21—C201.401 (2)C6—C51.391 (2)
N1—C11.386 (2)C10—C111.522 (3)
N1—C91.4463 (19)C10—H10A0.9700
N1—H10.8600C10—H10B0.9700
C16—C171.382 (2)C2—C31.373 (3)
C14—C151.442 (2)C2—H20.9300
C14—H140.9300C22—H22A0.9600
C9—C81.536 (2)C22—H22B0.9600
C9—H90.9800C22—H22C0.9600
C1—C21.398 (2)C12—C111.499 (3)
C1—C61.398 (2)C12—H12A0.9700
C17—C181.377 (2)C12—H12B0.9700
C17—H170.9300C5—C41.373 (3)
C18—C191.397 (2)C5—H50.9300
C18—C221.502 (2)C4—C31.372 (3)
C19—C201.374 (2)C4—H40.9300
C19—H190.9300C3—H30.9300
C20—H200.9300C11—H11A0.9700
O3—C121.431 (2)C11—H11B0.9700
O3—C71.4316 (19)
C15—O1—C16121.40 (12)O1—C15—C14117.37 (14)
C14—C13—C21118.25 (13)O3—C7—C6112.52 (14)
C14—C13—C9121.18 (13)O3—C7—C8111.57 (14)
C21—C13—C9120.56 (13)C6—C7—C8111.58 (12)
C16—C21—C20116.62 (13)O3—C7—H7106.9
C16—C21—C13117.98 (13)C6—C7—H7106.9
C20—C21—C13125.39 (13)C8—C7—H7106.9
C1—N1—C9120.93 (12)C5—C6—C1118.48 (16)
C1—N1—H1119.5C5—C6—C7121.39 (15)
C9—N1—H1119.5C1—C6—C7120.10 (14)
O1—C16—C17115.72 (13)C11—C10—C8110.52 (15)
O1—C16—C21121.83 (13)C11—C10—H10A109.5
C17—C16—C21122.45 (15)C8—C10—H10A109.5
C13—C14—C15123.12 (14)C11—C10—H10B109.5
C13—C14—H14118.4C8—C10—H10B109.5
C15—C14—H14118.4H10A—C10—H10B108.1
N1—C9—C13112.47 (12)C3—C2—C1120.53 (17)
N1—C9—C8108.27 (12)C3—C2—H2119.7
C13—C9—C8112.04 (12)C1—C2—H2119.7
N1—C9—H9108.0C18—C22—H22A109.5
C13—C9—H9108.0C18—C22—H22B109.5
C8—C9—H9108.0H22A—C22—H22B109.5
N1—C1—C2119.91 (14)C18—C22—H22C109.5
N1—C1—C6120.76 (14)H22A—C22—H22C109.5
C2—C1—C6119.33 (15)H22B—C22—H22C109.5
C18—C17—C16120.12 (14)O3—C12—C11111.81 (16)
C18—C17—H17119.9O3—C12—H12A109.3
C16—C17—H17119.9C11—C12—H12A109.3
C17—C18—C19118.40 (14)O3—C12—H12B109.3
C17—C18—C22120.50 (15)C11—C12—H12B109.3
C19—C18—C22121.10 (16)H12A—C12—H12B107.9
C20—C19—C18121.31 (15)C4—C5—C6121.58 (18)
C20—C19—H19119.3C4—C5—H5119.2
C18—C19—H19119.3C6—C5—H5119.2
C19—C20—C21120.98 (14)C3—C4—C5119.68 (18)
C19—C20—H20119.5C3—C4—H4120.2
C21—C20—H20119.5C5—C4—H4120.2
C12—O3—C7112.87 (13)C4—C3—C2120.39 (18)
C7—C8—C10110.95 (13)C4—C3—H3119.8
C7—C8—C9109.85 (13)C2—C3—H3119.8
C10—C8—C9111.42 (13)C12—C11—C10110.22 (15)
C7—C8—H8108.2C12—C11—H11A109.6
C10—C8—H8108.2C10—C11—H11A109.6
C9—C8—H8108.2C12—C11—H11B109.6
O2—C15—O1117.36 (14)C10—C11—H11B109.6
O2—C15—C14125.26 (16)H11A—C11—H11B108.1
C14—C13—C21—C16−2.2 (2)C13—C9—C8—C10171.57 (13)
C9—C13—C21—C16176.72 (13)C16—O1—C15—O2179.89 (15)
C14—C13—C21—C20176.89 (15)C16—O1—C15—C14−0.3 (2)
C9—C13—C21—C20−4.2 (2)C13—C14—C15—O2179.75 (18)
C15—O1—C16—C17178.94 (14)C13—C14—C15—O10.0 (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—C857.39 (19)
C13—C21—C16—O12.0 (2)C10—C8—C7—O3−52.89 (17)
C20—C21—C16—C173.2 (2)C9—C8—C7—O3−176.54 (12)
C13—C21—C16—C17−177.65 (14)C10—C8—C7—C673.92 (16)
C21—C13—C14—C151.3 (2)C9—C8—C7—C6−49.72 (16)
C9—C13—C14—C15−177.63 (14)N1—C1—C6—C5178.45 (15)
C1—N1—C9—C1381.22 (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—C7177.48 (14)
C21—C13—C9—N1169.30 (13)O3—C7—C6—C5−33.6 (2)
C14—C13—C9—C8110.44 (17)C8—C7—C6—C5−159.93 (15)
C21—C13—C9—C8−68.46 (18)O3—C7—C6—C1148.42 (14)
C9—N1—C1—C2−165.72 (14)C8—C7—C6—C122.1 (2)
C9—N1—C1—C615.3 (2)C7—C8—C10—C1151.00 (19)
O1—C16—C17—C18179.88 (14)C9—C8—C10—C11173.74 (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—C30.7 (2)
C16—C17—C18—C22177.53 (16)C7—O3—C12—C11−59.8 (2)
C17—C18—C19—C202.0 (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—C210.8 (3)C6—C5—C4—C30.7 (3)
C16—C21—C20—C19−3.3 (2)C5—C4—C3—C2−0.5 (3)
C13—C21—C20—C19177.62 (15)C1—C2—C3—C4−0.2 (3)
N1—C9—C8—C759.54 (15)O3—C12—C11—C1056.8 (2)
C13—C9—C8—C7−65.06 (16)C8—C10—C11—C12−52.7 (2)
N1—C9—C8—C10−63.82 (17)
D—H···AD—HH···AD···AD—H···A
C10—H10B···N10.972.582.947 (2)103
C12—H12A···O1i0.972.593.307 (3)131
C14—H14···N10.932.402.789 (2)105
C20—H20···O2ii0.932.403.275 (2)157
C5—H5···Cg5iii0.932.983.910 (3)173
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C12—H12A⋯O1i 0.972.593.307 (3)131
C20—H20⋯O2ii 0.932.403.275 (2)157

Symmetry codes: (i) ; (ii) .

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