Crystal structure of 7-bromo-2-(3-fluoro­phen­yl)-1-(methyl­sulfin­yl)naphtho[2,1-b]furan

Choi, H.D.; Lee, U.

doi:10.1107/S160053681401808X

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o1001-o1002

doi:10.1107/S160053681401808X

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Crystal structure of 7-bromo-2-(3-fluorophenyl)-1-(methylsulfinyl)naphtho[2,1-b]furan

Hong Dae Choi ^a and Uk Lee ^b ^*

^aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong, Busanjin-gu, Busan 614-714, Republic of Korea, and ^bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
^*Correspondence e-mail: uklee@pknu.ac.kr

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 6 August 2014; accepted 7 August 2014; online 13 August 2014)

In the title compound, C₁₉H₁₁BrFO₂S, the dihedral angle between the plane of the naphthofuran ring system [r.m.s. deviation = 0.043 (2) Å] and that of the 3-fluorobenzene ring is 39.32 (8)°. In the crystal, molecules are linked by C—H⋯O and C—Br⋯π [3.835 (1) Å] interactions into stacks along the c axis, forming a three-dimensional network. The F atom is disordered over two positions, with site-occupancy factors of 0.851 (3) and 0.149 (3).

Keywords: crystal structure; naphthofuran; 3-fluorobenzene; C—H⋯O interactions; C—Br⋯π interactions.

CCDC reference: 1018271

1. Related literature

For the pharmacological activities of compounds containing a naphthofuran ring, see: Debnath et al. (1993 ); Einhorn et al. (1984 ); Hranjec et al. (2003 ); Mahadevan & Vaidya (2003 ). For the fluorescence properties of compounds having a naphthofuran skeleton, see: Piloto et al. (2005 ). For the synthesis of the starting material 7-bromo-2-(3-fluorophenyl)-1-(methylsulfanyl)naphtho[2,1-b]furan, see: Choi et al. (1999 ). For a related structure, see: Choi et al. (2013 ).

2. Experimental

2.1. Crystal data

C₁₉H₁₂BrFO₂S
M_r = 403.26
Monoclinic, P 2₁ /c
a = 6.1340 (1) Å
b = 23.0602 (5) Å
c = 10.8806 (2) Å
β = 91.166 (1)°
V = 1538.76 (5) Å³
Z = 4
Mo Kα radiation
μ = 2.83 mm⁻¹
T = 173 K
0.74 × 0.45 × 0.38 mm

2.2. Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.229, T_max = 0.413
14935 measured reflections
3834 independent reflections
3033 reflections with I > 2σ(I)
R_int = 0.047

2.3. Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.098
S = 1.04
3834 reflections
228 parameters
14 restraints
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.91 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O2ⁱ	0.95	2.48	3.260 (3)	139
C19—H19B⋯O2ⁱ	0.98	2.56	3.387 (3)	142
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 1018271

Crystal structure: contains datablock I. DOI: 10.1107/S160053681401808X/tk5335sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681401808X/tk5335Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681401808X/tk5335Isup3.cml

checkCIF report

Structural commentary top

Many compounds involving a naphthofuran moiety show potent biological activities such as antibacterial, antitumor, anthelmintic and mutagenic properties (Debnath et al., 1993, Einhorn et al., 1984, Hranjec et al., 2003, Mahadevan et al., 2003). These naphthofuran derivatives are known about their fluorescence properties and potential utility as suitable fluorescent makers (Piloto et al., 2005). As a part of our ongoing project of 7-bromo-2-aryl-1-(methylsulfinyl)naphtho[2,1-b]furan derivatives containing 4-methylphenyl substituent in 2-position (Choi et al., 2013), we report herein on the crystal structure of the title compound.

In the title molecule (Fig. 1), the naphtho[2,1-b]furan unit is essentially planar, with a mean deviation of 0.043 (2) Å from the least-squares plane defined by the thirteen constituent atoms. The 3-fluorophenyl ring is essentially planar, with a mean deviation of 0.008 (2) Å from the least-squares plane defined by the six constituent atoms. In the 3-fluorophenyl ring, the F atom is disordered over two positions with site-occupancy factors, from refinement, of 0.851 (3) (part A) and 0.149 (3) (part B). The dihedral angle formed by the naphtho[2,1-bb]furan ring system and the 3-fluorophenyl ring is 39.32 (8)°. In the crystal structure (Fig. 2), molecules are linked by C—H···O hydrogen bonds (Table 1) and C6—Br1···π interactions between the bromine atom and the central benzene ring of a neighbouring molecule with a Br1···Cg1ⁱⁱ being 3.835 (1) Å (Cg1 is the centroid of the C2/C3/C8/C9/C10/C11 benzene ring), into stacks along the c-axis direction, forming a three-dimensional network.

Synthesis and crystallization top

The starting material 7-bromo-2-(3-fluorophenyl)-1-(methylsulfanyl)naphtho[2,1-b]furan was prepared by literature method (Choi et al., 1999). 3-Chloroperoxybenzoic acid (77%, 224 mg, 1.0 mmol) was added in small portions to a stirred solution of the starting material (355 mg, 0.9 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 4 h, the mixture was washed with saturated sodium bicarbonate solution (2 x 20 mL) and the organic layer was separated, dried over Mg₂SO₄, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane–ethyl acetate, 1:1 v/v) to afford the title compound as a colorless solid [yield 71% (258 mg); M.pt: 483–484 K; R_f = 0.48 (hexane–ethyl acetate, 1:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of an acetone solution (15 mL) of the title compound (23 mg) held at room temperature.

Refinement top

All H atoms were positioned geometrically and refined using a riding model with C—H = 0.95 Å for aryl and 0.98 Å for methyl H atoms, and with U_iso (H) = 1.2U_eq (C) for aryl and 1.5U_eq (C) for methyl H atoms. The positions of methyl hydrogens were optimized using the SHELXL-97 command AFIX 137 (Sheldrick, 2008). The F1 atom of the 3-fluorobenzene ring is disordered over two positions with site occupancy factors, from refinement, of 0.851 (3) (part A) and 0.149 (3) (part B). For the proper treatment of H-atoms, carbon atoms C15 and C17 were divided with equalized coordinates and displacement parameters. The distance of equivalent C—F pairs were restrained to 1.330 (5) Å using command DFIX, and displacement ellipsoids of F1 set were restrained to be approximately spherical using the ISOR command (parameter = 0.01).

Related literature top

For the pharmacological activities of compounds containing a naphthofuran ring, see: Debnath et al. (1993); Einhorn et al. (1984); Hranjec et al. (2003); Mahadevan & Vaidya (2003). For the fluorescence properties of compounds having a naphthofuran skeleton, see: Piloto et al. (2005). For the synthesis of the starting material 7-bromo-2-(3-fluorophenyl)-1-(methylsulfanyl)naphtho[2,1-b]furan, see: Choi et al. (1999). For a related structure, see: Choi et al. (2013).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius. The F atom of the 3-fluorobenzene ring is disordered over two positions with site occupancy factors, from refinement of 0.851 (3) (part A) and 0.149 (3) (part B).
	Fig. 2. A view of the C—H···O and C—Br···π interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding are omitted for clarity [Symmetry codes: (i) x, - y + 1/2, z + 1/2; (ii) x - 1, y, z; (iii) x, - y + 1/2, z - 1/2].

7-bromo-2-(3-fluorophenyl)-1-(methylsulfinyl) naphtho[2,1-b]furan top

Crystal data top

C₁₉H₁₂BrFO₂S	F(000) = 808
M_r = 403.26	D_x = 1.741 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 484 K–483 K K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 6.1340 (1) Å	Cell parameters from 5530 reflections
b = 23.0602 (5) Å	θ = 2.6–28.3°
c = 10.8806 (2) Å	µ = 2.83 mm⁻¹
β = 91.166 (1)°	T = 173 K
V = 1538.76 (5) Å³	Block, colourless
Z = 4	0.74 × 0.45 × 0.38 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3834 independent reflections
Radiation source: rotating anode	3033 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.047
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.4°, θ_min = 1.8°
ϕ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −30→19
T_min = 0.229, T_max = 0.413	l = −14→11
14935 measured reflections

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)] = 0.037	Hydrogen site location: difference Fourier map
wR(F²) = 0.098	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0539P)² + 0.2694P] where P = (F_o² + 2F_c²)/3
3834 reflections	(Δ/σ)_max = 0.001
228 parameters	Δρ_max = 0.47 e Å⁻³
14 restraints	Δρ_min = −0.91 e Å⁻³

Crystal data top

C₁₉H₁₂BrFO₂S	V = 1538.76 (5) Å³
M_r = 403.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.1340 (1) Å	µ = 2.83 mm⁻¹
b = 23.0602 (5) Å	T = 173 K
c = 10.8806 (2) Å	0.74 × 0.45 × 0.38 mm
β = 91.166 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3834 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3033 reflections with I > 2σ(I)
T_min = 0.229, T_max = 0.413	R_int = 0.047
14935 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	14 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.04	Δρ_max = 0.47 e Å⁻³
3834 reflections	Δρ_min = −0.91 e Å⁻³
228 parameters

Special details top

Experimental. ¹H NMR (δ p.p.m., CDCl₃, 400 Hz): 8.08-8.13 (m, 1H), 7.67-7.87 (m, 5H), 7.48-7.55 (m, 2H), 7.19-7.24 (m, 1H), 3.07 (s, 3H).

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	Occ. (<1)
Br1	−0.54910 (4)	0.387149 (11)	−0.05723 (2)	0.03031 (11)
S1	0.42612 (9)	0.27925 (2)	0.34599 (5)	0.01784 (14)
O1	0.5270 (3)	0.44696 (6)	0.37648 (14)	0.0183 (3)
O2	0.3848 (3)	0.25673 (7)	0.21917 (14)	0.0241 (4)
C1	0.4108 (4)	0.35599 (9)	0.34160 (19)	0.0149 (4)
C2	0.2686 (4)	0.39476 (9)	0.2724 (2)	0.0146 (5)
C3	0.0780 (4)	0.38989 (9)	0.1956 (2)	0.0153 (5)
C4	−0.0172 (4)	0.33718 (9)	0.1568 (2)	0.0184 (5)
H4	0.0479	0.3016	0.1821	0.022*
C5	−0.2012 (4)	0.33605 (10)	0.0835 (2)	0.0213 (5)
H5	−0.2627	0.3002	0.0574	0.026*
C6	−0.2975 (4)	0.38870 (9)	0.0474 (2)	0.0204 (5)
C7	−0.2122 (4)	0.44064 (10)	0.0813 (2)	0.0202 (5)
H7	−0.2804	0.4756	0.0548	0.024*
C8	−0.0216 (4)	0.44276 (9)	0.1562 (2)	0.0173 (5)
C9	0.0723 (4)	0.49734 (10)	0.1878 (2)	0.0208 (5)
H9	0.0030	0.5318	0.1595	0.025*
C10	0.2587 (4)	0.50152 (10)	0.2573 (2)	0.0206 (5)
H10	0.3233	0.5379	0.2767	0.025*
C11	0.3494 (4)	0.44945 (9)	0.2984 (2)	0.0169 (5)
C12	0.5593 (4)	0.38974 (9)	0.4033 (2)	0.0166 (5)
C13	0.7303 (4)	0.37854 (9)	0.4959 (2)	0.0170 (5)
C14	0.9160 (4)	0.41338 (10)	0.4996 (2)	0.0187 (5)
H14	0.9354	0.4434	0.4410	0.022*
C15A	1.0699 (4)	0.40315 (11)	0.5903 (2)	0.0253 (6)	0.851 (3)
F1A	1.2485 (3)	0.43617 (7)	0.59705 (16)	0.0334 (5)	0.851 (3)
C15B	1.0699 (4)	0.40315 (11)	0.5903 (2)	0.0253 (6)	0.15
H15B	1.1971	0.4267	0.5927	0.030*	0.149 (3)
C16	1.0499 (4)	0.36077 (11)	0.6776 (2)	0.0278 (6)
H16	1.1607	0.3544	0.7384	0.033*
C17A	0.8625 (4)	0.32773 (11)	0.6738 (2)	0.0273 (6)	0.851 (3)
H17A	0.8433	0.2984	0.7340	0.033*	0.851 (3)
C17B	0.8625 (4)	0.32773 (11)	0.6738 (2)	0.0273 (6)	0.15
F1B	0.8601 (17)	0.2943 (4)	0.7701 (6)	0.034 (3)	0.149 (3)
C18	0.7026 (4)	0.33614 (10)	0.5852 (2)	0.0204 (5)
H18	0.5741	0.3131	0.5850	0.025*
C19	0.1839 (4)	0.26492 (10)	0.4306 (2)	0.0236 (5)
H19A	0.0615	0.2866	0.3941	0.035*
H19B	0.2065	0.2770	0.5163	0.035*
H19C	0.1514	0.2233	0.4276	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02564 (16)	0.03656 (18)	0.02825 (17)	−0.00225 (11)	−0.01109 (11)	0.00308 (11)
S1	0.0209 (3)	0.0138 (3)	0.0187 (3)	0.0028 (2)	−0.0025 (2)	−0.0023 (2)
O1	0.0201 (8)	0.0164 (8)	0.0184 (8)	−0.0024 (6)	−0.0026 (7)	−0.0005 (6)
O2	0.0306 (10)	0.0204 (8)	0.0213 (9)	0.0033 (7)	−0.0002 (7)	−0.0066 (7)
C1	0.0173 (11)	0.0149 (10)	0.0127 (11)	0.0003 (9)	0.0011 (8)	−0.0005 (8)
C2	0.0183 (12)	0.0142 (10)	0.0114 (11)	−0.0001 (8)	0.0016 (9)	−0.0015 (8)
C3	0.0174 (11)	0.0181 (11)	0.0105 (10)	0.0019 (8)	0.0015 (9)	−0.0012 (8)
C4	0.0219 (12)	0.0151 (11)	0.0183 (11)	−0.0002 (9)	−0.0008 (9)	0.0002 (9)
C5	0.0219 (13)	0.0218 (12)	0.0202 (12)	−0.0023 (10)	−0.0017 (9)	−0.0018 (10)
C6	0.0180 (12)	0.0287 (13)	0.0144 (11)	0.0000 (10)	−0.0023 (9)	−0.0002 (9)
C7	0.0220 (12)	0.0228 (12)	0.0156 (11)	0.0043 (10)	−0.0017 (9)	0.0031 (9)
C8	0.0211 (12)	0.0186 (11)	0.0123 (11)	0.0025 (9)	0.0003 (8)	0.0006 (9)
C9	0.0307 (14)	0.0140 (11)	0.0175 (11)	0.0038 (9)	−0.0011 (10)	0.0011 (9)
C10	0.0290 (13)	0.0138 (11)	0.0191 (12)	−0.0013 (9)	0.0025 (10)	−0.0003 (9)
C11	0.0171 (11)	0.0195 (11)	0.0141 (11)	−0.0009 (9)	0.0004 (9)	0.0009 (9)
C12	0.0189 (12)	0.0157 (11)	0.0151 (11)	0.0012 (9)	0.0025 (9)	0.0014 (8)
C13	0.0172 (12)	0.0191 (11)	0.0149 (11)	0.0017 (9)	0.0002 (9)	−0.0045 (9)
C14	0.0202 (12)	0.0184 (11)	0.0175 (12)	0.0003 (9)	0.0015 (9)	−0.0047 (9)
C15A	0.0181 (13)	0.0272 (13)	0.0304 (14)	−0.0002 (10)	−0.0025 (10)	−0.0156 (11)
F1A	0.0217 (10)	0.0360 (10)	0.0424 (11)	−0.0107 (8)	−0.0036 (8)	−0.0071 (8)
C15B	0.0181 (13)	0.0272 (13)	0.0304 (14)	−0.0002 (10)	−0.0025 (10)	−0.0156 (11)
C16	0.0300 (15)	0.0291 (14)	0.0240 (13)	0.0119 (11)	−0.0108 (11)	−0.0091 (11)
C17A	0.0320 (15)	0.0277 (13)	0.0219 (13)	0.0057 (11)	−0.0043 (11)	−0.0012 (11)
C17B	0.0320 (15)	0.0277 (13)	0.0219 (13)	0.0057 (11)	−0.0043 (11)	−0.0012 (11)
F1B	0.040 (6)	0.037 (5)	0.024 (5)	−0.005 (4)	−0.017 (4)	0.000 (4)
C18	0.0218 (13)	0.0219 (12)	0.0176 (12)	−0.0013 (10)	−0.0001 (9)	−0.0003 (9)
C19	0.0306 (14)	0.0180 (11)	0.0222 (13)	−0.0029 (10)	0.0011 (10)	0.0005 (10)

Geometric parameters (Å, º) top

Br1—C6	1.899 (2)	C9—C10	1.361 (3)
S1—O2	1.4912 (16)	C9—H9	0.9500
S1—C1	1.773 (2)	C10—C11	1.393 (3)
S1—C19	1.795 (2)	C10—H10	0.9500
O1—C12	1.365 (2)	C12—C13	1.463 (3)
O1—C11	1.369 (3)	C13—C18	1.391 (3)
C1—C12	1.364 (3)	C13—C14	1.393 (3)
C1—C2	1.449 (3)	C14—C15A	1.373 (3)
C2—C11	1.382 (3)	C14—H14	0.9500
C2—C3	1.428 (3)	C15A—F1A	1.335 (3)
C3—C4	1.409 (3)	C15A—C16	1.370 (4)
C3—C8	1.426 (3)	C16—C17A	1.379 (4)
C4—C5	1.369 (3)	C16—H16	0.9500
C4—H4	0.9500	C17A—C18	1.375 (3)
C5—C6	1.403 (3)	C17A—H17A	0.9500
C5—H5	0.9500	C18—H18	0.9500
C6—C7	1.355 (3)	C19—H19A	0.9800
C7—C8	1.412 (3)	C19—H19B	0.9800
C7—H7	0.9500	C19—H19C	0.9800
C8—C9	1.424 (3)

O2—S1—C1	108.36 (10)	C9—C10—H10	121.9
O2—S1—C19	106.48 (11)	C11—C10—H10	121.9
C1—S1—C19	98.85 (11)	O1—C11—C2	111.47 (19)
C12—O1—C11	106.47 (17)	O1—C11—C10	122.9 (2)
C12—C1—C2	107.00 (18)	C2—C11—C10	125.6 (2)
C12—C1—S1	121.46 (17)	C1—C12—O1	110.71 (19)
C2—C1—S1	131.36 (16)	C1—C12—C13	134.5 (2)
C11—C2—C3	118.51 (19)	O1—C12—C13	114.64 (18)
C11—C2—C1	104.32 (19)	C18—C13—C14	119.8 (2)
C3—C2—C1	137.10 (19)	C18—C13—C12	120.6 (2)
C4—C3—C8	118.3 (2)	C14—C13—C12	119.5 (2)
C4—C3—C2	124.92 (19)	C15A—C14—C13	118.1 (2)
C8—C3—C2	116.73 (19)	C15A—C14—H14	120.9
C5—C4—C3	121.5 (2)	C13—C14—H14	120.9
C5—C4—H4	119.3	F1A—C15A—C16	117.0 (2)
C3—C4—H4	119.3	F1A—C15A—C14	119.6 (2)
C4—C5—C6	119.0 (2)	C16—C15A—C14	123.4 (2)
C4—C5—H5	120.5	C15A—C16—C17A	117.4 (2)
C6—C5—H5	120.5	C15A—C16—H16	121.3
C7—C6—C5	122.0 (2)	C17A—C16—H16	121.3
C7—C6—Br1	118.98 (17)	C18—C17A—C16	121.7 (2)
C5—C6—Br1	118.93 (17)	C18—C17A—H17A	119.2
C6—C7—C8	119.9 (2)	C16—C17A—H17A	119.2
C6—C7—H7	120.1	C17A—C18—C13	119.6 (2)
C8—C7—H7	120.1	C17A—C18—H18	120.2
C7—C8—C9	119.8 (2)	C13—C18—H18	120.2
C7—C8—C3	119.3 (2)	S1—C19—H19A	109.5
C9—C8—C3	121.0 (2)	S1—C19—H19B	109.5
C10—C9—C8	121.9 (2)	H19A—C19—H19B	109.5
C10—C9—H9	119.1	S1—C19—H19C	109.5
C8—C9—H9	119.1	H19A—C19—H19C	109.5
C9—C10—C11	116.3 (2)	H19B—C19—H19C	109.5

O2—S1—C1—C12	−136.65 (19)	C12—O1—C11—C2	−1.1 (3)
C19—S1—C1—C12	112.6 (2)	C12—O1—C11—C10	175.8 (2)
O2—S1—C1—C2	37.8 (2)	C3—C2—C11—O1	177.72 (19)
C19—S1—C1—C2	−73.0 (2)	C1—C2—C11—O1	0.1 (2)
C12—C1—C2—C11	0.9 (2)	C3—C2—C11—C10	1.0 (4)
S1—C1—C2—C11	−174.17 (18)	C1—C2—C11—C10	−176.6 (2)
C12—C1—C2—C3	−176.0 (3)	C9—C10—C11—O1	−175.0 (2)
S1—C1—C2—C3	9.0 (4)	C9—C10—C11—C2	1.4 (4)
C11—C2—C3—C4	177.0 (2)	C2—C1—C12—O1	−1.6 (3)
C1—C2—C3—C4	−6.4 (4)	S1—C1—C12—O1	174.03 (15)
C11—C2—C3—C8	−3.0 (3)	C2—C1—C12—C13	173.1 (2)
C1—C2—C3—C8	173.5 (2)	S1—C1—C12—C13	−11.2 (4)
C8—C3—C4—C5	−0.3 (3)	C11—O1—C12—C1	1.7 (3)
C2—C3—C4—C5	179.7 (2)	C11—O1—C12—C13	−174.20 (19)
C3—C4—C5—C6	−0.6 (4)	C1—C12—C13—C18	−34.8 (4)
C4—C5—C6—C7	1.0 (4)	O1—C12—C13—C18	139.7 (2)
C4—C5—C6—Br1	178.65 (18)	C1—C12—C13—C14	149.5 (3)
C5—C6—C7—C8	−0.6 (4)	O1—C12—C13—C14	−35.9 (3)
Br1—C6—C7—C8	−178.20 (17)	C18—C13—C14—C15A	2.0 (3)
C6—C7—C8—C9	177.6 (2)	C12—C13—C14—C15A	177.7 (2)
C6—C7—C8—C3	−0.3 (4)	C13—C14—C15A—F1A	−179.3 (2)
C4—C3—C8—C7	0.7 (3)	C13—C14—C15A—C16	−0.4 (4)
C2—C3—C8—C7	−179.2 (2)	F1A—C15A—C16—C17A	177.9 (2)
C4—C3—C8—C9	−177.1 (2)	C14—C15A—C16—C17A	−1.1 (4)
C2—C3—C8—C9	2.9 (3)	C15A—C16—C17A—C18	0.9 (4)
C7—C8—C9—C10	−178.4 (2)	C16—C17A—C18—C13	0.7 (4)
C3—C8—C9—C10	−0.6 (4)	C14—C13—C18—C17A	−2.2 (3)
C8—C9—C10—C11	−1.6 (3)	C12—C13—C18—C17A	−177.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O2ⁱ	0.95	2.48	3.260 (3)	139
C19—H19B···O2ⁱ	0.98	2.56	3.387 (3)	142

Symmetry code: (i) x, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O2ⁱ	0.95	2.48	3.260 (3)	139.4
C19—H19B···O2ⁱ	0.98	2.56	3.387 (3)	141.5

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

The X-ray centre of the Gyeongsang National University is acknowledged for providing access to the single-crystal diffractometer.

References

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Volume 70| Part 9| September 2014| Pages o1001-o1002

doi:10.1107/S160053681401808X

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

Crystal structure of 7-bromo-2-(3-fluoro­phen­yl)-1-(methyl­sulfin­yl)naphtho[2,1-b]furan

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 7-bromo-2-(3-fluorophenyl)-1-(methylsulfinyl)naphtho[2,1-b]furan