7-Bromo-2-(4-fluoro-phen-yl)-1-(methyl-sulfin-yl)naphtho[2,1-b]furan.

In the title compound, C(19)H(12)BrFO(2)S, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane through the naphthofuran fragment. The 4-fluoro-phenyl ring is rotated out of the naphthofuran plane, making a dihedral angle of 41.65 (7)°. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O and C-H⋯π inter-actions, and a short Br⋯F contact [3.046 (2) Å] occurs. The O atom of the sulfinyl group is disordered over two positions, with refined site-occupancy factors of 0.912 (4) and 0.088 (4).

Related literature

For the crystal structures of similar 7-bromo-2-phenyl­naphtho[2,1-b]furan derivatives, see: Choi et al. (2006 ▶, 2009 ▶). For the biological activity of naphthofuran compounds, see: Einhorn et al. (1984 ▶); Hranjec et al. (2003 ▶); Mahadevan & Vaidya (2003 ▶).

Experimental

Crystal data

C19H12BrFO2S

M = 403.26

Monoclinic,

a = 6.0155 (2) Å

b = 22.7143 (6) Å

c = 11.4364 (3) Å

β = 91.716 (1)°

V = 1561.94 (8) Å3

Z = 4

Mo Kα radiation

μ = 2.79 mm−1

T = 173 K

0.31 × 0.28 × 0.16 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.515, T max = 0.746

14194 measured reflections

3547 independent reflections

3086 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.078

S = 1.09

3547 reflections

228 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.66 e Å−3

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 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810011645/zl2274sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011645/zl2274Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H12BrFO2S	F(000) = 808
Mr = 403.26	Dx = 1.715 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6681 reflections
a = 6.0155 (2) Å	θ = 2.5–27.3°
b = 22.7143 (6) Å	µ = 2.79 mm−1
c = 11.4364 (3) Å	T = 173 K
β = 91.716 (1)°	Block, colourless
V = 1561.94 (8) Å3	0.31 × 0.28 × 0.16 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3547 independent reflections
Radiation source: Rotating Anode	3086 reflections with I > 2σ(I)
Bruker HELIOS graded multilayer optics	Rint = 0.031
Detector resolution: 10.0 pixels mm-1	θmax = 27.4°, θmin = 1.8°
φ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −29→28
Tmin = 0.515, Tmax = 0.746	l = −14→14
14194 measured reflections

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)] = 0.032	Hydrogen site location: difference Fourier map
wR(F2) = 0.078	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0285P)2 + 1.3174P] where P = (Fo2 + 2Fc2)/3
3547 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.55 e Å−3
1 restraint	Δρmin = −0.66 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br	−0.48150 (5)	0.382579 (12)	1.04709 (2)	0.03916 (10)
S	0.47791 (10)	0.28043 (2)	0.66043 (5)	0.02628 (13)
F	1.2163 (3)	0.36776 (7)	0.25403 (14)	0.0483 (4)
O1	0.5560 (3)	0.45183 (6)	0.62399 (13)	0.0243 (3)
O2A	0.4525 (3)	0.25792 (7)	0.78045 (15)	0.0328 (5)	0.912 (4)
O2B	0.6982 (13)	0.2602 (6)	0.6238 (14)	0.024 (5)	0.088 (4)
C1	0.4554 (4)	0.35832 (9)	0.66166 (18)	0.0218 (4)
C2	0.3135 (4)	0.39689 (9)	0.72727 (18)	0.0218 (4)
C3	0.1281 (4)	0.39074 (9)	0.80143 (17)	0.0224 (4)
C4	0.0413 (4)	0.33627 (10)	0.84002 (19)	0.0267 (5)
H4	0.1074	0.3013	0.8168	0.032*
C5	−0.1380 (4)	0.33420 (10)	0.9107 (2)	0.0302 (5)
H5	−0.1931	0.2982	0.9353	0.036*
C6	−0.2378 (4)	0.38667 (10)	0.94578 (19)	0.0284 (5)
C7	−0.1620 (4)	0.44040 (10)	0.91127 (18)	0.0281 (5)
H7	−0.2329	0.4746	0.9349	0.034*
C8	0.0242 (4)	0.44381 (9)	0.83966 (18)	0.0245 (4)
C9	0.1093 (4)	0.49995 (9)	0.80711 (18)	0.0272 (5)
H9	0.0393	0.5338	0.8332	0.033*
C10	0.2894 (4)	0.50541 (9)	0.73923 (18)	0.0265 (5)
H10	0.3465	0.5420	0.7197	0.032*
C11	0.3846 (4)	0.45309 (9)	0.70009 (17)	0.0226 (4)
C12	0.5951 (4)	0.39335 (9)	0.60055 (18)	0.0222 (4)
C13	0.7632 (4)	0.38339 (9)	0.51270 (18)	0.0227 (4)
C14	0.7334 (4)	0.34109 (10)	0.42469 (19)	0.0275 (5)
H14	0.6091	0.3167	0.4245	0.033*
C15	0.8873 (4)	0.33521 (10)	0.3378 (2)	0.0314 (5)
H15	0.8682	0.3072	0.2791	0.038*
C16	1.0688 (4)	0.37188 (10)	0.3406 (2)	0.0322 (5)
C17	1.1043 (4)	0.41416 (10)	0.4261 (2)	0.0295 (5)
H17	1.2296	0.4382	0.4256	0.035*
C18	0.9504 (4)	0.41994 (9)	0.51190 (19)	0.0252 (4)
H18	0.9708	0.4483	0.5698	0.030*
C19	0.2271 (4)	0.26380 (10)	0.5786 (2)	0.0328 (5)
H19A	0.2018	0.2221	0.5796	0.049*
H19B	0.2409	0.2768	0.4993	0.049*
H19C	0.1042	0.2836	0.6131	0.049*

	U11	U22	U33	U12	U13	U23
Br	0.03555 (15)	0.05091 (17)	0.03161 (14)	−0.01198 (11)	0.01077 (10)	−0.00502 (11)
S	0.0273 (3)	0.0176 (2)	0.0338 (3)	0.0016 (2)	−0.0020 (2)	0.0026 (2)
F	0.0514 (10)	0.0486 (9)	0.0464 (9)	0.0068 (8)	0.0279 (8)	−0.0001 (7)
O1	0.0293 (8)	0.0186 (7)	0.0251 (7)	−0.0030 (6)	0.0028 (6)	0.0004 (6)
O2A	0.0417 (12)	0.0238 (9)	0.0326 (10)	−0.0001 (8)	−0.0051 (8)	0.0102 (7)
O2B	0.036 (11)	0.010 (7)	0.025 (9)	−0.003 (7)	0.003 (7)	0.007 (6)
C1	0.0228 (11)	0.0192 (9)	0.0233 (10)	0.0001 (8)	−0.0023 (8)	0.0019 (8)
C2	0.0258 (11)	0.0199 (10)	0.0193 (9)	0.0000 (8)	−0.0033 (8)	0.0016 (7)
C3	0.0263 (11)	0.0229 (10)	0.0177 (9)	−0.0020 (8)	−0.0031 (8)	0.0008 (8)
C4	0.0294 (12)	0.0228 (10)	0.0277 (11)	−0.0014 (9)	−0.0008 (9)	0.0027 (8)
C5	0.0323 (13)	0.0297 (11)	0.0285 (11)	−0.0081 (10)	−0.0003 (9)	0.0042 (9)
C6	0.0257 (12)	0.0389 (13)	0.0207 (10)	−0.0049 (10)	0.0013 (8)	0.0001 (9)
C7	0.0320 (13)	0.0304 (11)	0.0218 (10)	0.0015 (9)	0.0009 (9)	−0.0005 (9)
C8	0.0298 (12)	0.0257 (10)	0.0178 (9)	0.0006 (9)	−0.0012 (8)	0.0001 (8)
C9	0.0392 (14)	0.0205 (10)	0.0219 (10)	0.0034 (9)	0.0031 (9)	−0.0010 (8)
C10	0.0378 (13)	0.0184 (10)	0.0234 (10)	−0.0017 (9)	0.0014 (9)	0.0006 (8)
C11	0.0254 (11)	0.0227 (10)	0.0198 (10)	−0.0024 (8)	0.0004 (8)	0.0006 (8)
C12	0.0254 (11)	0.0187 (10)	0.0222 (10)	−0.0003 (8)	−0.0032 (8)	−0.0007 (7)
C13	0.0237 (11)	0.0220 (10)	0.0222 (10)	0.0012 (8)	−0.0008 (8)	0.0030 (8)
C14	0.0298 (12)	0.0241 (10)	0.0286 (11)	−0.0009 (9)	−0.0007 (9)	−0.0006 (9)
C15	0.0408 (14)	0.0267 (11)	0.0269 (11)	0.0049 (10)	0.0028 (10)	−0.0031 (9)
C16	0.0353 (14)	0.0326 (12)	0.0294 (12)	0.0094 (10)	0.0094 (10)	0.0058 (9)
C17	0.0255 (12)	0.0281 (11)	0.0349 (12)	−0.0001 (9)	0.0015 (9)	0.0082 (9)
C18	0.0271 (12)	0.0231 (10)	0.0250 (11)	0.0002 (9)	−0.0032 (9)	0.0011 (8)
C19	0.0353 (14)	0.0251 (11)	0.0375 (13)	−0.0045 (10)	−0.0070 (10)	−0.0012 (9)

F—Bri	3.0457 (15)	C7—H7	0.9300
Br—C6	1.898 (2)	C8—C9	1.428 (3)
S—O2B	1.475 (3)	C9—C10	1.357 (3)
S—O2A	1.4769 (18)	C9—H9	0.9300
S—C1	1.775 (2)	C10—C11	1.399 (3)
S—C19	1.792 (2)	C10—H10	0.9300
F—C16	1.352 (3)	C12—C13	1.464 (3)
O1—C11	1.370 (3)	C13—C18	1.399 (3)
O1—C12	1.377 (2)	C13—C14	1.399 (3)
C1—C12	1.365 (3)	C14—C15	1.385 (3)
C1—C2	1.448 (3)	C14—H14	0.9300
C2—C11	1.384 (3)	C15—C16	1.373 (4)
C2—C3	1.428 (3)	C15—H15	0.9300
C3—C4	1.419 (3)	C16—C17	1.383 (3)
C3—C8	1.432 (3)	C17—C18	1.376 (3)
C4—C5	1.368 (3)	C17—H17	0.9300
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.398 (3)	C19—H19A	0.9600
C5—H5	0.9300	C19—H19B	0.9600
C6—C7	1.365 (3)	C19—H19C	0.9600
C7—C8	1.409 (3)
C16—F—Bri	168.86 (14)	C8—C9—H9	119.0
O2B—S—O2A	106.0 (6)	C9—C10—C11	116.5 (2)
O2B—S—C1	112.5 (6)	C9—C10—H10	121.7
O2A—S—C1	109.13 (10)	C11—C10—H10	121.7
O2B—S—C19	122.4 (7)	O1—C11—C2	111.52 (18)
O2A—S—C19	107.67 (12)	O1—C11—C10	122.99 (19)
C1—S—C19	98.68 (11)	C2—C11—C10	125.4 (2)
C11—O1—C12	106.28 (16)	C1—C12—O1	110.56 (19)
C12—C1—C2	107.11 (18)	C1—C12—C13	135.23 (19)
C12—C1—S	121.91 (17)	O1—C12—C13	114.09 (17)
C2—C1—S	130.82 (16)	C18—C13—C14	119.3 (2)
C11—C2—C3	118.38 (19)	C18—C13—C12	119.03 (19)
C11—C2—C1	104.53 (18)	C14—C13—C12	121.5 (2)
C3—C2—C1	137.00 (19)	C15—C14—C13	120.5 (2)
C4—C3—C2	124.9 (2)	C15—C14—H14	119.7
C4—C3—C8	118.1 (2)	C13—C14—H14	119.7
C2—C3—C8	117.05 (18)	C16—C15—C14	118.3 (2)
C5—C4—C3	121.2 (2)	C16—C15—H15	120.9
C5—C4—H4	119.4	C14—C15—H15	120.9
C3—C4—H4	119.4	F—C16—C15	118.7 (2)
C4—C5—C6	119.5 (2)	F—C16—C17	118.4 (2)
C4—C5—H5	120.2	C15—C16—C17	122.9 (2)
C6—C5—H5	120.2	C18—C17—C16	118.5 (2)
C7—C6—C5	121.9 (2)	C18—C17—H17	120.7
C7—C6—Br	119.41 (18)	C16—C17—H17	120.7
C5—C6—Br	118.63 (17)	C17—C18—C13	120.5 (2)
C6—C7—C8	119.7 (2)	C17—C18—H18	119.8
C6—C7—H7	120.2	C13—C18—H18	119.8
C8—C7—H7	120.2	S—C19—H19A	109.5
C7—C8—C9	119.9 (2)	S—C19—H19B	109.5
C7—C8—C3	119.5 (2)	H19A—C19—H19B	109.5
C9—C8—C3	120.6 (2)	S—C19—H19C	109.5
C10—C9—C8	122.0 (2)	H19A—C19—H19C	109.5
C10—C9—H9	119.0	H19B—C19—H19C	109.5
O2B—S—C1—C12	19.7 (7)	C8—C9—C10—C11	1.6 (3)
O2A—S—C1—C12	137.02 (18)	C12—O1—C11—C2	0.6 (2)
C19—S—C1—C12	−110.77 (19)	C12—O1—C11—C10	−176.4 (2)
O2B—S—C1—C2	−155.0 (7)	C3—C2—C11—O1	−177.03 (17)
O2A—S—C1—C2	−37.8 (2)	C1—C2—C11—O1	0.1 (2)
C19—S—C1—C2	74.5 (2)	C3—C2—C11—C10	−0.1 (3)
C12—C1—C2—C11	−0.7 (2)	C1—C2—C11—C10	177.0 (2)
S—C1—C2—C11	174.62 (17)	C9—C10—C11—O1	174.94 (19)
C12—C1—C2—C3	175.5 (2)	C9—C10—C11—C2	−1.7 (3)
S—C1—C2—C3	−9.1 (4)	C2—C1—C12—O1	1.2 (2)
C11—C2—C3—C4	−177.8 (2)	S—C1—C12—O1	−174.72 (14)
C1—C2—C3—C4	6.3 (4)	C2—C1—C12—C13	−174.4 (2)
C11—C2—C3—C8	1.9 (3)	S—C1—C12—C13	9.8 (4)
C1—C2—C3—C8	−174.0 (2)	C11—O1—C12—C1	−1.1 (2)
C2—C3—C4—C5	−179.7 (2)	C11—O1—C12—C13	175.45 (17)
C8—C3—C4—C5	0.7 (3)	C1—C12—C13—C18	−146.4 (2)
C3—C4—C5—C6	0.0 (3)	O1—C12—C13—C18	38.2 (3)
C4—C5—C6—C7	0.2 (4)	C1—C12—C13—C14	38.3 (4)
C4—C5—C6—Br	−178.44 (17)	O1—C12—C13—C14	−137.1 (2)
C5—C6—C7—C8	−1.0 (4)	C18—C13—C14—C15	0.2 (3)
Br—C6—C7—C8	177.61 (16)	C12—C13—C14—C15	175.5 (2)
C6—C7—C8—C9	−177.6 (2)	C13—C14—C15—C16	0.0 (3)
C6—C7—C8—C3	1.6 (3)	C14—C15—C16—F	−177.9 (2)
C4—C3—C8—C7	−1.5 (3)	C14—C15—C16—C17	0.1 (4)
C2—C3—C8—C7	178.87 (19)	F—C16—C17—C18	177.6 (2)
C4—C3—C8—C9	177.7 (2)	C15—C16—C17—C18	−0.3 (4)
C2—C3—C8—C9	−2.0 (3)	C16—C17—C18—C13	0.5 (3)
C7—C8—C9—C10	179.4 (2)	C14—C13—C18—C17	−0.5 (3)
C3—C8—C9—C10	0.2 (3)	C12—C13—C18—C17	−175.9 (2)

Cg is the centroid of the C2/C3/C8/C9/C10/C11 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O2Aii	0.93	2.53	3.235 (3)	133
C18—H18···Cgiii	0.93	2.65	3.347 (3)	132

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2/C3/C8/C9/C10/C11 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O2Ai	0.93	2.53	3.235 (3)	133
C18—H18⋯Cgii	0.93	2.65	3.347 (3)	132

Symmetry codes: (i) ; (ii) .