Crystal structure of methyl 3-(3-fluoro­phen­yl)-1-methyl-1,3a,4,9b-tetra­hydro-3H-thio­chromeno[4,3-c]isoxazole-3a-carboxyl­ate

Savithri, M.P.; Suresh, M.; Raghunathan, R.; Vimala, G.; SubbiahPandi, A.

doi:10.1107/S2056989015013651

organic compounds

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ISSN: 2056-9890

Volume 71| Part 8| August 2015| Pages o600-o601

https://doi.org/10.1107/S2056989015013651

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Crystal structure of methyl 3-(3-fluorophenyl)-1-methyl-1,3a,4,9b-tetrahydro-3H-thiochromeno[4,3-c]isoxazole-3a-carboxylate

M. P. Savithri,^a M. Suresh,^b R. Raghunathan,^b G. Vimala ^c and A. SubbiahPandi ^c,^a ^*

^aDepartment of Physics, Queen Mary's College (Autonomous), Chennai 600 004, India, ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and ^cDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India
^*Correspondence e-mail: aspandian59@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 6 July 2015; accepted 17 July 2015; online 25 July 2015)

In the title compound, C₁₉H₁₈FNO₃S, the five-membered oxazolidine ring adopts an envelope conformation with the methine C atom of the fused bond as the flap. Its mean plane is oriented at a dihedral angle of 50.38 (1)° with respect to the fluorophenyl ring. The six-membered thiopyran ring has a half-chair conformation and its mean plane is almost coplanar with the fused benzene ring, making a dihedral angle of 4.94 (10)°. The two aromatic rings are inclined to one another by 85.96 (11)°, and the mean planes of the oxazolidine and thiopyran rings are inclined to one another by 57.64 (12)°. In the crystal, molecules are linked by C—H⋯π interactions, forming a three-dimensional structure.

Keywords: crystal structure; oxazolidine; thiopyran; thiochromenone; C—H⋯π interactions.

CCDC reference: 1413525

1. Related literature

For background on thio-containing heterocyclic rings and for related structures, see for example: Khan et al. (2008a ,b ).

2. Experimental

2.1. Crystal data

C₁₉H₁₈FNO₃S
M_r = 359.40
Monoclinic, P 2₁ /n
a = 10.7729 (8) Å
b = 12.6361 (8) Å
c = 12.625 (1) Å
β = 92.992 (3)°
V = 1716.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 K
0.30 × 0.30 × 0.25 mm

2.2. Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.938, T_max = 0.948
18645 measured reflections
3024 independent reflections
2456 reflections with I > 2σ(I)
R_int = 0.026

2.3. Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.123
S = 0.99
3024 reflections
243 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 and Cg4 are the centroids of rings C2–C7 and C11–C16, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cg4ⁱ	0.93	2.75	3.479 (3)	136
C13—H13⋯Cg3ⁱⁱ	0.93	2.74	3.599 (3)	153
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z+2.

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 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1413525

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989015013651/su5169sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015013651/su5169Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015013651/su5169Isup3.cml

checkCIF report

Structural commentary top

Small substituted heterocyclic compounds play an important role in the development of biologically active substances by offering a high structural diversity. In view of their biological importance, the title compound was synthesized and we report herein on its crystal structure.

The molecular structure of the title compound is illustrated in Fig. 1. The five-membered oxazolidine ring [O1/N1/C8—C10] exhibits an envelope conformation with atom C8 as the flap [asymmetry parameter ΔCs(C8) = 2.6 (2)° and puckering parameters of q₂ = 0.483 (2)Å and φ₂ = 256.6 (3)°]. Its mean pane is oriented at a dihedral angle of 50.38 (13)° with respect to the fluorophenyl ring (C11—C16). The six membered thiopyran ring (S1/C1/C2/C7/C8/C10) has a half-chair conformation and its mean plane is almost coplanar with the fused benzene ring (C2—C7) with a dihedral angle = 4.94 (10) °. This aromatic ring is almost normal to the fluorophenyl ring with a dihedral angle of 85.96 (11) °. The sum of angles at atom N1 of the pyrrolidine ring (320°) is in accordance with sp³ hybridization.

In the crystal, molecules are linked by C—H···π interactions forming a three-dimensional structure (Table 1).

The crystal structures of 7-nitro-5H-1-benzothiopyrano[2,3-b]- pyridin-5-one (Khan et al., 2008a) and 5H-1-benzothiopyrano[2,3-b] pyridin-5-one (Khan et al., 2008b), are similar to that of the title compound.

Synthesis and crystallization top

To a solution of methyl (Z)-2-(((2-formylphenyl)thio)methyl)-3-phenylacrylate (1 mmol) and N-methyl hydroxylamine hydrochloride (1.1 mmol) in acetonitrile (10 ml) was added pyridine (0.2 mmol). The solution was refluxed until the completion of the reaction (monitored by TLC). The solvent was then removed under vacuum. The crude product was subjected to column chromatography on silica gel (100-200 mesh) using petroleum ether-ethyl acetate (9:1) as eluent, which successfully provided the pure product as a colorless solid. The product was dissolved in chloroform and heated for 2 min. The resulting solution was subjected to crystallization by slow evaporation of the solvent for 48 h resulting in the formation of single crystals of the title compound.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. The H atoms attached to atom C1 were freely refined. All other H atoms were fixed geometrically and allowed to ride on their parent atoms: C—H = 0.93–0.98 Å with U_iso(H) = 1.5U_eq(C) for methyl H atoms and 1.2U_eq(C) for other H atoms.

Related literature top

For background on thio-containing heterocyclic rings and for related structures, see for example: Khan et al. (2008a,b).

Structure description top

In the crystal, molecules are linked by C—H···π interactions forming a three-dimensional structure (Table 1).

For background on thio-containing heterocyclic rings and for related structures, see for example: Khan et al. (2008a,b).

Synthesis and crystallization top

Refinement details top

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 for Windows (Farrugia, 2012); 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 the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Methyl 3-(3-fluorophenyl)-1-methyl-1,3a,4,9b-tetrahydro-3H-thiochromeno[4,3-c]isoxazole-3a-carboxylate top

Crystal data top

C₁₉H₁₈FNO₃S	F(000) = 752
M_r = 359.40	D_x = 1.391 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3024 reflections
a = 10.7729 (8) Å	θ = 2.3–25.0°
b = 12.6361 (8) Å	µ = 0.22 mm⁻¹
c = 12.625 (1) Å	T = 293 K
β = 92.992 (3)°	Block, colourless
V = 1716.3 (2) Å³	0.30 × 0.30 × 0.25 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3024 independent reflections
Radiation source: fine-focus sealed tube	2456 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω and φ scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→12
T_min = 0.938, T_max = 0.948	k = −15→15
18645 measured reflections	l = −15→13

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)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.123	w = 1/[σ²(F_o²) + (0.0547P)² + 1.7913P] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max < 0.001
3024 reflections	Δρ_max = 0.52 e Å⁻³
243 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0079 (14)

Crystal data top

C₁₉H₁₈FNO₃S	V = 1716.3 (2) Å³
M_r = 359.40	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.7729 (8) Å	µ = 0.22 mm⁻¹
b = 12.6361 (8) Å	T = 293 K
c = 12.625 (1) Å	0.30 × 0.30 × 0.25 mm
β = 92.992 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3024 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2456 reflections with I > 2σ(I)
T_min = 0.938, T_max = 0.948	R_int = 0.026
18645 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.52 e Å⁻³
3024 reflections	Δρ_min = −0.24 e Å⁻³
243 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
S1	0.38912 (6)	−0.09256 (5)	0.73827 (6)	0.0484 (2)
O3	0.14448 (16)	0.08198 (17)	0.72833 (14)	0.0580 (6)
O1	0.44199 (15)	0.19965 (17)	0.95772 (13)	0.0560 (5)
F1	−0.09742 (14)	0.14114 (17)	1.01633 (15)	0.0759 (6)
C7	0.54244 (19)	0.08164 (16)	0.70941 (16)	0.0285 (5)
C2	0.5127 (2)	−0.02335 (18)	0.68520 (17)	0.0344 (5)
C10	0.34366 (18)	0.10865 (17)	0.81229 (16)	0.0288 (5)
C9	0.3219 (2)	0.18273 (19)	0.90866 (17)	0.0342 (5)
C8	0.47396 (19)	0.14639 (17)	0.78729 (16)	0.0285 (5)
C17	0.25020 (19)	0.13405 (18)	0.72143 (16)	0.0331 (5)
C11	0.2322 (2)	0.14500 (17)	0.98805 (16)	0.0314 (5)
C1	0.3454 (2)	−0.00741 (18)	0.84444 (18)	0.0344 (5)
C16	0.1063 (2)	0.16036 (18)	0.96619 (18)	0.0370 (5)
H16	0.0780	0.1928	0.9034	0.044*
C14	0.0609 (3)	0.0799 (2)	1.1315 (2)	0.0494 (7)
H14	0.0030	0.0583	1.1791	0.059*
C6	0.6370 (2)	0.12968 (19)	0.65535 (18)	0.0359 (5)
H6	0.6571	0.1999	0.6700	0.043*
C12	0.2719 (2)	0.0969 (2)	1.08214 (19)	0.0435 (6)
H12	0.3562	0.0861	1.0977	0.052*
C4	0.6718 (2)	−0.0280 (2)	0.55821 (19)	0.0455 (6)
H4	0.7149	−0.0649	0.5081	0.055*
C5	0.7016 (2)	0.0757 (2)	0.58066 (19)	0.0426 (6)
H5	0.7647	0.1091	0.5459	0.051*
C3	0.5789 (2)	−0.0770 (2)	0.60926 (19)	0.0442 (6)
H3	0.5594	−0.1472	0.5933	0.053*
C15	0.0242 (2)	0.1273 (2)	1.0381 (2)	0.0443 (6)
C13	0.1858 (3)	0.0649 (2)	1.1532 (2)	0.0525 (7)
H13	0.2130	0.0328	1.2165	0.063*
C19	0.6429 (2)	0.2148 (2)	0.9055 (2)	0.0502 (7)
H19A	0.6781	0.2105	0.9768	0.075*
H19B	0.6183	0.2864	0.8902	0.075*
H19C	0.7036	0.1929	0.8570	0.075*
C18	0.0474 (3)	0.1068 (3)	0.6484 (3)	0.0771 (11)
H18A	−0.0251	0.0652	0.6606	0.116*
H18B	0.0759	0.0911	0.5794	0.116*
H18C	0.0270	0.1806	0.6524	0.116*
N1	0.53515 (17)	0.14612 (15)	0.89425 (14)	0.0357 (5)
O2	0.26780 (16)	0.19605 (16)	0.65350 (14)	0.0534 (5)
H1B	0.264 (2)	−0.0329 (19)	0.8609 (18)	0.038 (6)*
H1A	0.403 (2)	−0.0170 (19)	0.902 (2)	0.039 (6)*
H8	0.469 (2)	0.2167 (19)	0.7624 (17)	0.030 (6)*
H9	0.294 (2)	0.249 (2)	0.8768 (19)	0.037 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0561 (4)	0.0372 (4)	0.0531 (4)	−0.0166 (3)	0.0129 (3)	−0.0116 (3)
O3	0.0359 (9)	0.0920 (15)	0.0446 (10)	−0.0205 (9)	−0.0129 (8)	0.0205 (10)
O1	0.0364 (9)	0.0935 (15)	0.0382 (10)	−0.0165 (9)	0.0046 (7)	−0.0286 (10)
F1	0.0360 (9)	0.1030 (15)	0.0885 (13)	0.0088 (9)	0.0031 (8)	−0.0189 (11)
C7	0.0278 (10)	0.0316 (11)	0.0257 (10)	0.0021 (8)	−0.0016 (8)	0.0039 (8)
C2	0.0364 (12)	0.0367 (12)	0.0299 (11)	0.0004 (10)	−0.0013 (9)	−0.0009 (9)
C10	0.0277 (11)	0.0351 (11)	0.0234 (10)	−0.0018 (9)	0.0002 (8)	0.0002 (9)
C9	0.0367 (12)	0.0381 (13)	0.0276 (11)	0.0003 (10)	−0.0007 (9)	−0.0011 (10)
C8	0.0299 (11)	0.0270 (11)	0.0283 (11)	−0.0015 (8)	−0.0019 (9)	0.0013 (9)
C17	0.0294 (11)	0.0443 (13)	0.0255 (11)	0.0005 (9)	0.0013 (9)	−0.0022 (10)
C11	0.0343 (11)	0.0336 (11)	0.0263 (11)	0.0049 (9)	0.0027 (9)	−0.0032 (9)
C1	0.0346 (12)	0.0361 (12)	0.0325 (12)	−0.0065 (10)	0.0030 (10)	0.0011 (10)
C16	0.0376 (12)	0.0389 (13)	0.0342 (12)	0.0084 (10)	−0.0017 (10)	−0.0039 (10)
C14	0.0585 (17)	0.0457 (15)	0.0462 (15)	−0.0087 (12)	0.0220 (13)	−0.0039 (12)
C6	0.0331 (11)	0.0378 (12)	0.0368 (12)	0.0033 (9)	0.0017 (9)	0.0067 (10)
C12	0.0433 (14)	0.0528 (15)	0.0343 (13)	0.0136 (11)	0.0031 (10)	0.0062 (11)
C4	0.0452 (14)	0.0588 (16)	0.0329 (13)	0.0151 (12)	0.0067 (11)	−0.0033 (11)
C5	0.0375 (13)	0.0552 (15)	0.0358 (13)	0.0082 (11)	0.0084 (10)	0.0105 (11)
C3	0.0521 (15)	0.0423 (14)	0.0382 (13)	0.0043 (11)	0.0015 (11)	−0.0095 (11)
C15	0.0309 (12)	0.0481 (14)	0.0545 (16)	0.0000 (10)	0.0071 (11)	−0.0169 (12)
C13	0.0671 (18)	0.0536 (16)	0.0377 (14)	0.0109 (14)	0.0107 (13)	0.0133 (12)
C19	0.0375 (13)	0.0671 (18)	0.0456 (15)	−0.0126 (12)	−0.0028 (11)	−0.0141 (13)
C18	0.0421 (16)	0.127 (3)	0.0600 (19)	−0.0163 (18)	−0.0212 (14)	0.0236 (19)
N1	0.0334 (10)	0.0433 (11)	0.0299 (10)	−0.0046 (8)	−0.0039 (8)	−0.0046 (8)
O2	0.0442 (10)	0.0722 (13)	0.0432 (10)	−0.0029 (9)	−0.0048 (8)	0.0240 (9)

Geometric parameters (Å, º) top

S1—C2	1.755 (2)	C1—H1A	0.94 (3)
S1—C1	1.801 (2)	C16—C15	1.366 (3)
O3—C17	1.322 (3)	C16—H16	0.9300
O3—C18	1.449 (3)	C14—C15	1.363 (4)
O1—C9	1.422 (3)	C14—C13	1.372 (4)
O1—N1	1.480 (2)	C14—H14	0.9300
F1—C15	1.336 (3)	C6—C5	1.381 (3)
C7—C6	1.395 (3)	C6—H6	0.9300
C7—C2	1.395 (3)	C12—C13	1.383 (4)
C7—C8	1.502 (3)	C12—H12	0.9300
C2—C3	1.400 (3)	C4—C3	1.367 (4)
C10—C17	1.520 (3)	C4—C5	1.375 (4)
C10—C1	1.522 (3)	C4—H4	0.9300
C10—C8	1.531 (3)	C5—H5	0.9300
C10—C9	1.562 (3)	C3—H3	0.9300
C9—C11	1.505 (3)	C13—H13	0.9300
C9—H9	0.97 (3)	C19—N1	1.450 (3)
C8—N1	1.471 (3)	C19—H19A	0.9600
C8—H8	0.94 (2)	C19—H19B	0.9600
C17—O2	1.184 (3)	C19—H19C	0.9600
C11—C12	1.382 (3)	C18—H18A	0.9600
C11—C16	1.384 (3)	C18—H18B	0.9600
C1—H1B	0.97 (2)	C18—H18C	0.9600

C2—S1—C1	102.68 (11)	C11—C16—H16	120.4
C17—O3—C18	116.1 (2)	C15—C14—C13	118.1 (2)
C9—O1—N1	108.84 (15)	C15—C14—H14	121.0
C6—C7—C2	118.2 (2)	C13—C14—H14	121.0
C6—C7—C8	118.65 (19)	C5—C6—C7	121.7 (2)
C2—C7—C8	123.12 (19)	C5—C6—H6	119.1
C7—C2—C3	119.4 (2)	C7—C6—H6	119.1
C7—C2—S1	124.10 (17)	C11—C12—C13	119.9 (2)
C3—C2—S1	116.34 (18)	C11—C12—H12	120.1
C17—C10—C1	113.77 (18)	C13—C12—H12	120.1
C17—C10—C8	110.91 (17)	C3—C4—C5	120.3 (2)
C1—C10—C8	110.89 (18)	C3—C4—H4	119.9
C17—C10—C9	109.91 (17)	C5—C4—H4	119.9
C1—C10—C9	111.71 (17)	C4—C5—C6	119.4 (2)
C8—C10—C9	98.67 (16)	C4—C5—H5	120.3
O1—C9—C11	111.01 (18)	C6—C5—H5	120.3
O1—C9—C10	105.01 (17)	C4—C3—C2	121.0 (2)
C11—C9—C10	117.17 (19)	C4—C3—H3	119.5
O1—C9—H9	108.1 (14)	C2—C3—H3	119.5
C11—C9—H9	110.6 (14)	F1—C15—C14	118.2 (2)
C10—C9—H9	104.4 (14)	F1—C15—C16	119.1 (2)
N1—C8—C7	112.81 (17)	C14—C15—C16	122.7 (2)
N1—C8—C10	100.47 (16)	C14—C13—C12	120.9 (2)
C7—C8—C10	116.89 (17)	C14—C13—H13	119.5
N1—C8—H8	108.8 (13)	C12—C13—H13	119.5
C7—C8—H8	108.5 (13)	N1—C19—H19A	109.5
C10—C8—H8	109.0 (13)	N1—C19—H19B	109.5
O2—C17—O3	123.2 (2)	H19A—C19—H19B	109.5
O2—C17—C10	124.1 (2)	N1—C19—H19C	109.5
O3—C17—C10	112.58 (19)	H19A—C19—H19C	109.5
C12—C11—C16	119.3 (2)	H19B—C19—H19C	109.5
C12—C11—C9	122.1 (2)	O3—C18—H18A	109.5
C16—C11—C9	118.6 (2)	O3—C18—H18B	109.5
C10—C1—S1	112.17 (15)	H18A—C18—H18B	109.5
C10—C1—H1B	112.2 (14)	O3—C18—H18C	109.5
S1—C1—H1B	103.7 (14)	H18A—C18—H18C	109.5
C10—C1—H1A	109.2 (15)	H18B—C18—H18C	109.5
S1—C1—H1A	108.2 (15)	C19—N1—C8	113.99 (19)
H1B—C1—H1A	111 (2)	C19—N1—O1	103.60 (17)
C15—C16—C11	119.1 (2)	C8—N1—O1	102.23 (15)
C15—C16—H16	120.4

C6—C7—C2—C3	0.8 (3)	O1—C9—C11—C12	−22.1 (3)
C8—C7—C2—C3	178.1 (2)	C10—C9—C11—C12	98.5 (3)
C6—C7—C2—S1	−175.09 (16)	O1—C9—C11—C16	157.1 (2)
C8—C7—C2—S1	2.2 (3)	C10—C9—C11—C16	−82.3 (3)
C1—S1—C2—C7	−12.6 (2)	C17—C10—C1—S1	61.9 (2)
C1—S1—C2—C3	171.40 (18)	C8—C10—C1—S1	−63.9 (2)
N1—O1—C9—C11	130.75 (19)	C9—C10—C1—S1	−172.93 (15)
N1—O1—C9—C10	3.2 (2)	C2—S1—C1—C10	42.50 (19)
C17—C10—C9—O1	−146.89 (19)	C12—C11—C16—C15	−0.2 (3)
C1—C10—C9—O1	85.8 (2)	C9—C11—C16—C15	−179.4 (2)
C8—C10—C9—O1	−30.8 (2)	C2—C7—C6—C5	−0.9 (3)
C17—C10—C9—C11	89.4 (2)	C8—C7—C6—C5	−178.3 (2)
C1—C10—C9—C11	−37.9 (3)	C16—C11—C12—C13	−0.1 (4)
C8—C10—C9—C11	−154.55 (19)	C9—C11—C12—C13	179.1 (2)
C6—C7—C8—N1	−87.2 (2)	C3—C4—C5—C6	0.1 (4)
C2—C7—C8—N1	95.5 (2)	C7—C6—C5—C4	0.4 (3)
C6—C7—C8—C10	157.06 (19)	C5—C4—C3—C2	−0.1 (4)
C2—C7—C8—C10	−20.2 (3)	C7—C2—C3—C4	−0.3 (4)
C17—C10—C8—N1	162.34 (17)	S1—C2—C3—C4	175.88 (19)
C1—C10—C8—N1	−70.2 (2)	C13—C14—C15—F1	179.4 (2)
C9—C10—C8—N1	47.06 (19)	C13—C14—C15—C16	−0.2 (4)
C17—C10—C8—C7	−75.3 (2)	C11—C16—C15—F1	−179.3 (2)
C1—C10—C8—C7	52.1 (2)	C11—C16—C15—C14	0.3 (4)
C9—C10—C8—C7	169.45 (17)	C15—C14—C13—C12	−0.1 (4)
C18—O3—C17—O2	−1.6 (4)	C11—C12—C13—C14	0.2 (4)
C18—O3—C17—C10	176.2 (2)	C7—C8—N1—C19	77.3 (2)
C1—C10—C17—O2	−142.9 (2)	C10—C8—N1—C19	−157.50 (19)
C8—C10—C17—O2	−17.1 (3)	C7—C8—N1—O1	−171.62 (16)
C9—C10—C17—O2	90.9 (3)	C10—C8—N1—O1	−46.41 (19)
C1—C10—C17—O3	39.4 (3)	C9—O1—N1—C19	146.0 (2)
C8—C10—C17—O3	165.18 (19)	C9—O1—N1—C8	27.3 (2)
C9—C10—C17—O3	−86.8 (2)

Hydrogen-bond geometry (Å, º) top

Cg3 and Cg4 are the centroids of rings C2–C7 and C11–C16, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cg4ⁱ	0.93	2.75	3.479 (3)	136
C13—H13···Cg3ⁱⁱ	0.93	2.74	3.599 (3)	153

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

Hydrogen-bond geometry (Å, º) top

Cg3 and Cg4 are the centroids of rings C2–C7 and C11–C16, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cg4ⁱ	0.93	2.75	3.479 (3)	136
C13—H13···Cg3ⁱⁱ	0.93	2.74	3.599 (3)	153

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

Acknowledgements

MPS and ASP thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

References

Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Khan, M. N., Tahir, M. N., Khan, M. A., Khan, I. U. & Arshad, M. N. (2008a). Acta Cryst. E64, o730. Web of Science CSD CrossRef IUCr Journals Google Scholar
Khan, M. N., Tahir, M. N., Khan, M. A., Khan, I. U. & Arshad, M. N. (2008b). Acta Cryst. E64, o1704. 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

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Volume 71| Part 8| August 2015| Pages o600-o601

https://doi.org/10.1107/S2056989015013651

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

Crystal structure of methyl 3-(3-fluoro­phen­yl)-1-methyl-1,3a,4,9b-tetra­hydro-3H-thio­chromeno[4,3-c]isoxazole-3a-carboxyl­ate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of methyl 3-(3-fluorophenyl)-1-methyl-1,3a,4,9b-tetrahydro-3H-thiochromeno[4,3-c]isoxazole-3a-carboxylate