Methyl 3-(4-fluoro­phen­yl)-1-methyl-1,2,3,3a,4,9b-hexa­hydro­chromeno[4,3-b]pyrrole-3a-carboxyl­ate

Chitra Devi, G.; Bhaskaran, S.; Usha, G.; Murugan, G.; Bakthadoss, M.

doi:10.1107/S1600536810054036

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o349

doi:10.1107/S1600536810054036

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Methyl 3-(4-fluorophenyl)-1-methyl-1,2,3,3a,4,9b-hexahydrochromeno[4,3-b]pyrrole-3a-carboxylate

G. Chitra Devi,^a Sundari Bhaskaran,^a G. Usha,^a ^* G. Murugan ^b and M. Bakthadoss ^b

^aDepartment of Physics, Queen Mary's College (A), Chennai-4, Tamilnadu, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai-25, Tamilnadu, India
^*Correspondence e-mail: guqmc@yahoo.com

(Received 9 December 2010; accepted 24 December 2010; online 12 January 2011)

In the title compound, C₂₀H₂₀FNO₃, the pyrrolidine and benzopyran rings adopt half chair and twisted half chair conformations, respectively. The carboxylate group is almost perpendicular to the pyran ring [89.4 (1)°].

Related literature

Chromanone derivatives are used as intermediates in the synthesis of natural products calonlide (A) and inophyllum (B) (Ellis et al., 1977 ), which have been suggested to have activity against anti-human immuno deficiency virus type 1 (HIV-1) (Hussain & Amir, 1986 ). Chromanone derivatives dilate the heart and act as remedies for angina pectoris, see: Hasegnaida (1967 ). Pyrrolidine derivatives possess anti-influenza (Stylianakis et al., 2003 ) and anti-convulsant (Obniska et al., 2002 ) activity. For related structures, see: Abdul Ajees et al. (2002 ); Usha et al. (2003 ). For asymmetry parameters, see: Nardelli (1983 ).

Experimental

Crystal data

C₂₀H₂₀FNO₃
M_r = 341.37
Monoclinic, P 2₁ /c
a = 10.4519 (4) Å
b = 20.6778 (8) Å
c = 7.8508 (3) Å
β = 91.535 (2)°
V = 1696.12 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.22 × 0.20 × 0.19 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
16737 measured reflections
4237 independent reflections
2844 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.219
S = 0.81
4237 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ); cell refinement: 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 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810054036/bx2338sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810054036/bx2338Isup2.hkl

checkCIF report

Comment top

Chromanone derivatives are used as a varsatile intermediate in the synthesis of natural products calonlide(A) and inophyllum(B), (Ellis et al., 1977) which have been suggested to have activity against anti-human immuno deficiency virus type1 (HIV-1) (Hussain et al., 1986). Chromanone derivatives dilate the heart and act as remedies for angina pectoris (Hasegnaida, 1967). Spiropyrrolidine derivatives are often used in the synthesis of biologically active compounds. Spiro ring system is also very interesting from a biogenetic point of view. Synthetic pyrrolidine derivatives have activity against the aldose reductase enzyme, which controls influenza. Pyrrolidine derivatives possess anti-influenza (Stylianakis et al., 2003) and anti- convulsant (Obniska et al., 2002) activity. We report here the crystal structure of the title compound, Fig.1. The C—C, N—C, C—O bond lengths in the structure are close to those found in the related structures (Usha et al., 2003; Abdul Ajees et al., 2002). The sum of the angle around atom N (332°) indicates sp³ hybridization. The carboxylate group is perpendicular to the pyran ring [89.4 (1)°].The pyran ring adopts twist-half chair conformation with lowest asymmetry parameters (Nardelli, 1983) of Δ (C9—C5) =0.033 (1) and the pyrrole ring adopts half chair conformation Δs(C8) = 0.008 (1). The molecular conformation is stabilizaed by two weak C—H···N and C—H···O intramolecular interactions, Table 1. The crystal packing is stabilized by van der Waals forces.

Related literature top

Chromanone derivatives are used as intermediates in the synthesis of natural products calonlide (A) and inophyllum (B) (Ellis et al., 1977), which have been suggested to have activity against anti-human immuno deficiency virus type 1 (HIV-1) (Hussain & Amir, 1986). Chromanone derivatives dilate the heart and act as remedies for angina pectoris, see: Hasegnaida (1967). Pyrrolidine derivatives possess anti-influenza (Stylianakis et al., 2003) and anti-convulsant (Obniska et al., 2002) activity. For related structures, see: Abdul Ajees et al. (2002); Usha et al. (2003). For related literature, see: Nardelli (1983).

Experimental top

A mixture of (E)-methyl2-((2-formylphenoxy) methyl)-3-(4-fluorophenyl)acrylate(2 mmol) and sarcosine (2 mmol) in acetonitrile (8 ml) was refluxed for 5h. After the completion of the reaction mixture was concentrated and the resulting crude mass was diluted with water (15 ml). The combined organic layer was washed with brine (2x10ml) and dried over anhydrous Na₂SO_4.The organic layer was concentrated and purified by column chromatographyon silica gel (Acme 100–200 mesh), using ethyl acetate-hexanes (1:9) to afford the pure title of the compound as a colourless solid in 65% yield.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: 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 for Windows (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, with displacement ellipsoids drawn at the 30% probability level.

Methyl 3-(4-fluorophenyl)-1-methyl-1,2,3,3a,4,9b- hexahydrochromeno[4,3-b]pyrrole-3a-carboxylate top

Crystal data top

C₂₀H₂₀FNO₃	F(000) = 720
M_r = 341.37	D_x = 1.337 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4237 reflections
a = 10.4519 (4) Å	θ = 2–28°
b = 20.6778 (8) Å	µ = 0.10 mm⁻¹
c = 7.8508 (3) Å	T = 293 K
β = 91.535 (2)°	Block, colourless
V = 1696.12 (11) Å³	0.22 × 0.20 × 0.19 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	2844 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.035
Graphite monochromator	θ_max = 28.4°, θ_min = 2.0°
ω and ϕ scan	h = −13→13
16737 measured reflections	k = −27→27
4237 independent reflections	l = −10→10

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)] = 0.045	H-atom parameters constrained
wR(F²) = 0.219	w = 1/[σ²(F_o²) + (0.2P)²] where P = (F_o² + 2F_c²)/3
S = 0.81	(Δ/σ)_max < 0.001
4237 reflections	Δρ_max = 0.24 e Å⁻³
227 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 constraints	Extinction coefficient: 0.013 (4)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₂₀H₂₀FNO₃	V = 1696.12 (11) Å³
M_r = 341.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.4519 (4) Å	µ = 0.10 mm⁻¹
b = 20.6778 (8) Å	T = 293 K
c = 7.8508 (3) Å	0.22 × 0.20 × 0.19 mm
β = 91.535 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2844 reflections with I > 2σ(I)
16737 measured reflections	R_int = 0.035
4237 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.219	H-atom parameters constrained
S = 0.81	Δρ_max = 0.24 e Å⁻³
4237 reflections	Δρ_min = −0.18 e Å⁻³
227 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
C20	0.1861 (2)	0.22098 (11)	0.9717 (3)	0.0645 (6)
H20A	0.1703	0.2651	0.9389	0.097*
H20B	0.2338	0.2201	1.0780	0.097*
H20C	0.1060	0.1990	0.9845	0.097*
O1	0.53935 (13)	0.05675 (7)	0.87998 (17)	0.0559 (4)
F	−0.01102 (13)	−0.15643 (6)	0.7317 (2)	0.0775 (5)
C1	0.63732 (18)	0.20543 (10)	0.6667 (2)	0.0505 (5)
H1	0.6080	0.2352	0.5858	0.061*
C2	0.7536 (2)	0.21569 (12)	0.7493 (3)	0.0655 (6)
H2	0.8025	0.2518	0.7236	0.079*
C3	0.7969 (2)	0.17199 (14)	0.8701 (3)	0.0737 (7)
H3	0.8757	0.1785	0.9253	0.088*
C4	0.7248 (2)	0.11893 (12)	0.9099 (3)	0.0640 (6)
H4	0.7545	0.0898	0.9922	0.077*
C5	0.60721 (17)	0.10867 (9)	0.8271 (2)	0.0458 (4)
C6	0.42920 (17)	0.03806 (8)	0.7786 (2)	0.0422 (4)
H6A	0.3763	0.0094	0.8447	0.051*
H6B	0.4569	0.0143	0.6796	0.051*
C7	0.35015 (15)	0.09573 (8)	0.72016 (18)	0.0357 (4)
C8	0.43498 (15)	0.14033 (8)	0.61491 (19)	0.0359 (4)
H8	0.3916	0.1818	0.5955	0.043*
C9	0.56300 (16)	0.15160 (8)	0.7018 (2)	0.0398 (4)
C10	0.24295 (16)	0.07657 (8)	0.58563 (19)	0.0383 (4)
H10	0.1776	0.1105	0.5884	0.046*
C11	0.30986 (18)	0.08318 (10)	0.4144 (2)	0.0485 (5)
H11A	0.3104	0.0420	0.3554	0.058*
H11B	0.2657	0.1146	0.3425	0.058*
C12	0.17597 (15)	0.01306 (8)	0.62225 (18)	0.0373 (4)
C13	0.06850 (16)	0.01298 (9)	0.7231 (2)	0.0440 (4)
H13	0.0382	0.0520	0.7649	0.053*
C14	0.00570 (18)	−0.04361 (10)	0.7628 (2)	0.0515 (5)
H14	−0.0650	−0.0433	0.8323	0.062*
C15	0.05039 (18)	−0.09990 (9)	0.6970 (2)	0.0503 (5)
C16	0.1548 (2)	−0.10261 (9)	0.5965 (3)	0.0540 (5)
H16	0.1828	−0.1418	0.5532	0.065*
C17	0.21785 (17)	−0.04557 (9)	0.5604 (2)	0.0475 (4)
H17	0.2898	−0.0467	0.4932	0.057*
C18	0.49406 (18)	0.14114 (10)	0.3144 (2)	0.0501 (5)
H18A	0.4949	0.1146	0.2141	0.075*
H18B	0.5799	0.1542	0.3444	0.075*
H18C	0.4424	0.1788	0.2925	0.075*
C19	0.28728 (16)	0.12722 (8)	0.87041 (19)	0.0397 (4)
N	0.44108 (14)	0.10458 (7)	0.45389 (16)	0.0395 (4)
O2	0.25895 (16)	0.09942 (7)	0.99746 (16)	0.0637 (5)
O3	0.25839 (14)	0.18923 (6)	0.84246 (17)	0.0556 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C20	0.0666 (14)	0.0625 (13)	0.0655 (13)	0.0059 (10)	0.0216 (11)	−0.0122 (10)
O1	0.0514 (8)	0.0618 (8)	0.0535 (8)	−0.0039 (6)	−0.0194 (6)	0.0170 (6)
F	0.0686 (9)	0.0619 (8)	0.1021 (11)	−0.0257 (6)	0.0022 (8)	0.0114 (7)
C1	0.0503 (10)	0.0546 (11)	0.0470 (10)	−0.0087 (8)	0.0096 (8)	−0.0091 (8)
C2	0.0541 (12)	0.0807 (15)	0.0623 (13)	−0.0264 (11)	0.0128 (10)	−0.0206 (11)
C3	0.0476 (12)	0.111 (2)	0.0623 (14)	−0.0190 (13)	−0.0064 (10)	−0.0203 (13)
C4	0.0501 (12)	0.0916 (17)	0.0497 (11)	−0.0018 (11)	−0.0114 (9)	−0.0022 (10)
C5	0.0411 (9)	0.0571 (11)	0.0391 (9)	0.0006 (8)	−0.0026 (7)	−0.0023 (7)
C6	0.0451 (9)	0.0424 (9)	0.0387 (8)	−0.0015 (7)	−0.0065 (7)	0.0064 (6)
C7	0.0374 (8)	0.0414 (9)	0.0281 (7)	−0.0010 (6)	−0.0008 (6)	0.0035 (6)
C8	0.0375 (8)	0.0386 (8)	0.0316 (7)	0.0014 (6)	0.0028 (6)	0.0048 (6)
C9	0.0382 (9)	0.0447 (10)	0.0364 (8)	−0.0022 (7)	0.0028 (7)	−0.0052 (6)
C10	0.0396 (8)	0.0442 (9)	0.0309 (8)	−0.0015 (7)	−0.0031 (6)	0.0040 (6)
C11	0.0512 (10)	0.0646 (12)	0.0294 (8)	−0.0137 (9)	−0.0015 (7)	0.0043 (7)
C12	0.0343 (8)	0.0473 (10)	0.0300 (7)	−0.0023 (7)	−0.0021 (6)	0.0005 (6)
C13	0.0386 (9)	0.0537 (11)	0.0398 (9)	−0.0001 (7)	0.0023 (7)	−0.0068 (7)
C14	0.0385 (9)	0.0679 (13)	0.0481 (10)	−0.0096 (8)	0.0047 (8)	−0.0005 (8)
C15	0.0448 (10)	0.0505 (11)	0.0554 (11)	−0.0122 (8)	−0.0055 (8)	0.0064 (8)
C16	0.0533 (11)	0.0453 (11)	0.0632 (12)	0.0009 (8)	−0.0009 (9)	−0.0061 (8)
C17	0.0401 (9)	0.0540 (11)	0.0486 (10)	0.0000 (8)	0.0077 (7)	−0.0046 (8)
C18	0.0481 (10)	0.0679 (12)	0.0345 (8)	−0.0039 (9)	0.0060 (7)	0.0094 (8)
C19	0.0403 (9)	0.0481 (10)	0.0305 (8)	−0.0058 (7)	−0.0014 (6)	0.0015 (7)
N	0.0420 (8)	0.0486 (8)	0.0280 (6)	−0.0016 (6)	0.0018 (5)	0.0029 (5)
O2	0.0889 (12)	0.0667 (10)	0.0364 (7)	0.0026 (7)	0.0172 (7)	0.0078 (6)
O3	0.0688 (9)	0.0489 (8)	0.0502 (7)	0.0061 (6)	0.0222 (6)	0.0000 (6)

Geometric parameters (Å, º) top

C20—O3	1.440 (2)	C8—C9	1.504 (2)
C20—H20A	0.9600	C8—H8	0.9800
C20—H20B	0.9600	C10—C12	1.519 (2)
C20—H20C	0.9600	C10—C11	1.538 (2)
O1—C5	1.358 (2)	C10—H10	0.9800
O1—C6	1.435 (2)	C11—N	1.466 (2)
F—C15	1.364 (2)	C11—H11A	0.9700
C1—C2	1.379 (3)	C11—H11B	0.9700
C1—C9	1.389 (2)	C12—C17	1.382 (3)
C1—H1	0.9300	C12—C13	1.392 (2)
C2—C3	1.378 (4)	C13—C14	1.381 (3)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.371 (4)	C14—C15	1.361 (3)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.391 (3)	C15—C16	1.365 (3)
C4—H4	0.9300	C16—C17	1.384 (3)
C5—C9	1.395 (3)	C16—H16	0.9300
C6—C7	1.515 (2)	C17—H17	0.9300
C6—H6A	0.9700	C18—N	1.453 (2)
C6—H6B	0.9700	C18—H18A	0.9600
C7—C19	1.513 (2)	C18—H18B	0.9600
C7—C8	1.536 (2)	C18—H18C	0.9600
C7—C10	1.570 (2)	C19—O2	1.1953 (19)
C8—N	1.467 (2)	C19—O3	1.334 (2)

O3—C20—H20A	109.5	C12—C10—C11	117.71 (14)
O3—C20—H20B	109.5	C12—C10—C7	114.52 (12)
H20A—C20—H20B	109.5	C11—C10—C7	103.45 (12)
O3—C20—H20C	109.5	C12—C10—H10	106.8
H20A—C20—H20C	109.5	C11—C10—H10	106.8
H20B—C20—H20C	109.5	C7—C10—H10	106.8
C5—O1—C6	117.45 (13)	N—C11—C10	106.67 (12)
C2—C1—C9	121.4 (2)	N—C11—H11A	110.4
C2—C1—H1	119.3	C10—C11—H11A	110.4
C9—C1—H1	119.3	N—C11—H11B	110.4
C3—C2—C1	119.4 (2)	C10—C11—H11B	110.4
C3—C2—H2	120.3	H11A—C11—H11B	108.6
C1—C2—H2	120.3	C17—C12—C13	117.85 (16)
C2—C3—C4	120.6 (2)	C17—C12—C10	122.69 (15)
C2—C3—H3	119.7	C13—C12—C10	119.46 (15)
C4—C3—H3	119.7	C14—C13—C12	121.66 (17)
C3—C4—C5	119.9 (2)	C14—C13—H13	119.2
C3—C4—H4	120.0	C12—C13—H13	119.2
C5—C4—H4	120.0	C15—C14—C13	117.96 (16)
O1—C5—C4	116.08 (17)	C15—C14—H14	121.0
O1—C5—C9	123.58 (16)	C13—C14—H14	121.0
C4—C5—C9	120.30 (18)	C14—C15—C16	122.85 (17)
O1—C6—C7	112.27 (14)	C14—C15—F	119.26 (17)
O1—C6—H6A	109.1	C16—C15—F	117.89 (17)
C7—C6—H6A	109.1	C15—C16—C17	118.42 (17)
O1—C6—H6B	109.1	C15—C16—H16	120.8
C7—C6—H6B	109.1	C17—C16—H16	120.8
H6A—C6—H6B	107.9	C12—C17—C16	121.23 (17)
C19—C7—C6	110.33 (13)	C12—C17—H17	119.4
C19—C7—C8	115.48 (13)	C16—C17—H17	119.4
C6—C7—C8	108.52 (13)	N—C18—H18A	109.5
C19—C7—C10	108.43 (13)	N—C18—H18B	109.5
C6—C7—C10	112.26 (13)	H18A—C18—H18B	109.5
C8—C7—C10	101.62 (12)	N—C18—H18C	109.5
N—C8—C9	114.21 (13)	H18A—C18—H18C	109.5
N—C8—C7	101.54 (12)	H18B—C18—H18C	109.5
C9—C8—C7	111.63 (13)	O2—C19—O3	122.65 (16)
N—C8—H8	109.7	O2—C19—C7	124.48 (17)
C9—C8—H8	109.7	O3—C19—C7	112.74 (13)
C7—C8—H8	109.7	C18—N—C8	114.43 (14)
C1—C9—C5	118.24 (16)	C18—N—C11	111.78 (13)
C1—C9—C8	122.01 (16)	C8—N—C11	105.79 (13)
C5—C9—C8	119.69 (15)	C19—O3—C20	116.29 (15)

C9—C1—C2—C3	−0.5 (3)	C8—C7—C10—C11	26.42 (16)
C1—C2—C3—C4	−0.6 (4)	C12—C10—C11—N	−127.87 (15)
C2—C3—C4—C5	0.4 (4)	C7—C10—C11—N	−0.45 (18)
C6—O1—C5—C4	−169.32 (16)	C11—C10—C12—C17	31.4 (2)
C6—O1—C5—C9	12.9 (3)	C7—C10—C12—C17	−90.51 (19)
C3—C4—C5—O1	−176.91 (19)	C11—C10—C12—C13	−149.15 (15)
C3—C4—C5—C9	1.0 (3)	C7—C10—C12—C13	88.96 (18)
C5—O1—C6—C7	−42.6 (2)	C17—C12—C13—C14	0.8 (2)
O1—C6—C7—C19	−68.27 (17)	C10—C12—C13—C14	−178.74 (15)
O1—C6—C7—C8	59.16 (17)	C12—C13—C14—C15	−1.4 (3)
O1—C6—C7—C10	170.67 (13)	C13—C14—C15—C16	0.9 (3)
C19—C7—C8—N	−160.23 (13)	C13—C14—C15—F	−178.91 (17)
C6—C7—C8—N	75.34 (14)	C14—C15—C16—C17	0.1 (3)
C10—C7—C8—N	−43.13 (15)	F—C15—C16—C17	179.98 (17)
C19—C7—C8—C9	77.68 (16)	C13—C12—C17—C16	0.4 (3)
C6—C7—C8—C9	−46.75 (17)	C10—C12—C17—C16	179.85 (16)
C10—C7—C8—C9	−165.22 (13)	C15—C16—C17—C12	−0.8 (3)
C2—C1—C9—C5	1.8 (3)	C6—C7—C19—O2	−28.0 (2)
C2—C1—C9—C8	178.95 (16)	C8—C7—C19—O2	−151.46 (17)
O1—C5—C9—C1	175.64 (16)	C10—C7—C19—O2	95.34 (19)
C4—C5—C9—C1	−2.1 (3)	C6—C7—C19—O3	156.20 (14)
O1—C5—C9—C8	−1.5 (3)	C8—C7—C19—O3	32.72 (18)
C4—C5—C9—C8	−179.23 (16)	C10—C7—C19—O3	−80.49 (16)
N—C8—C9—C1	88.40 (19)	C9—C8—N—C18	−71.69 (18)
C7—C8—C9—C1	−157.13 (15)	C7—C8—N—C18	168.03 (13)
N—C8—C9—C5	−94.54 (18)	C9—C8—N—C11	164.82 (14)
C7—C8—C9—C5	19.9 (2)	C7—C8—N—C11	44.53 (15)
C19—C7—C10—C12	−82.09 (17)	C10—C11—N—C18	−152.67 (15)
C6—C7—C10—C12	40.05 (19)	C10—C11—N—C8	−27.52 (18)
C8—C7—C10—C12	155.80 (13)	O2—C19—O3—C20	−2.3 (3)
C19—C7—C10—C11	148.52 (14)	C7—C19—O3—C20	173.64 (16)
C6—C7—C10—C11	−89.33 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6B···N	0.97	2.58	2.902 (2)	100
C8—H8···O3	0.98	2.42	2.792 (2)	102

Experimental details

Crystal data
Chemical formula	C₂₀H₂₀FNO₃
M_r	341.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.4519 (4), 20.6778 (8), 7.8508 (3)
β (°)	91.535 (2)
V (Å³)	1696.12 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.22 × 0.20 × 0.19

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	16737, 4237, 2844
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.219, 0.81
No. of reflections	4237
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.18

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6B···N	0.97	2.58	2.902 (2)	100
C8—H8···O3	0.98	2.42	2.792 (2)	102

Acknowledgements

The authors thank Professor D. Velmurugan, Centre for Advanced Study in Crystallography and Biophysics, University of Madras, for providing data-collection and computing facilities.

References

Abdul Ajees, A., Manikandan, S. & Raghunathan, R. (2002). Acta Cryst. E58, o802–o804. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2004). APEX2 and SAINT. BrukerAXS Inc., Madison,Wisconsin, USA. Google Scholar
Ellis, G. P., Lockhart, I. M., Meeder-Nyez, D. & Schweizer, E. E. (1977). Chromenes, Chromanones and Chromones, edited by G. P. Ellis. New York: John Wiley and Sons, Inc. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hasegnaida, G. (1967). Chem. Abst. 69, 67221. Google Scholar
Hussain, M. I. & Amir, M. (1986). J. Indian Chem. Soc. 63, 317–320. Google Scholar
Nardelli, M. (1983). Acta Cryst. C39, 1141–1142. CrossRef CAS Web of Science IUCr Journals Google Scholar
Obniska, J., Zeic, A. & Zagorska, A. (2002). Acta Pol. Pharm. 59, 209–213. 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
Stylianakis, I., Kolocouris, N., Fytas, G., Foscolos, G. B., Padalko, E., Neyts, J. & Declereq, E. (2003). Bioorg. Med. Chem. Lett. 10, 1699–1703. Web of Science CrossRef Google Scholar
Usha, G., Selvanayagam, S., Yogavel, M., Velmurugan, D., Amalraj, A., Raghunathan, R., Shanmuga Sundara Raj, S. & Fun, H.-K. (2003). Acta Cryst. E59, o1572–o1574. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 2| February 2011| Page o349

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

Methyl 3-(4-fluoro­phen­yl)-1-methyl-1,2,3,3a,4,9b-hexa­hydro­chromeno[4,3-b]pyrrole-3a-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Methyl 3-(4-fluorophenyl)-1-methyl-1,2,3,3a,4,9b-hexahydrochromeno[4,3-b]pyrrole-3a-carboxylate