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

In the title compound, C(19)H(12)BrFO(3)S, the 4-fluoro-phenyl ring makes a dihedral angle of 80.32 (5)° with the mean plane of the naphtho-furan fragment. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O and C-H⋯π inter-actions. The crystal structure also exhibits aromatic π-π inter-actions between the central benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.564 (3) Å].

Related literature

For the pharmacological activity of naphtho­furan compounds, see: Einhorn et al. (1984 ▶); Hranjec et al. (2003 ▶); Mahadevan & Vaidya (2003 ▶). For our previous structural studies of related 1-aryl­sulfonyl-7-bromo-2-methyl­naphtho­[2,1-b]furan derivatives, see: Choi et al. (2008a ▶,b ▶).

Experimental

Crystal data

C19H12BrFO3S

M = 419.26

Monoclinic,

a = 12.0415 (2) Å

b = 8.1579 (1) Å

c = 17.4578 (3) Å

β = 105.325 (1)°

V = 1653.96 (5) Å3

Z = 4

Mo Kα radiation

μ = 2.64 mm−1

T = 173 K

0.25 × 0.21 × 0.12 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.553, T max = 0.744

14803 measured reflections

3803 independent reflections

3026 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.078

S = 1.02

3803 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.41 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/S160053681005436X/rk2255sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681005436X/rk2255Isup2.hkl

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

C19H12BrFO3S	F(000) = 840
Mr = 419.26	Dx = 1.684 Mg m−3
Monoclinic, P21/n	Melting point = 485–486 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 12.0415 (2) Å	Cell parameters from 4448 reflections
b = 8.1579 (1) Å	θ = 2.4–27.4°
c = 17.4578 (3) Å	µ = 2.64 mm−1
β = 105.325 (1)°	T = 173 K
V = 1653.96 (5) Å3	Block, colourless
Z = 4	0.25 × 0.21 × 0.12 mm

Bruker SMART APEXII CCD diffractometer	3803 independent reflections
Radiation source: rotating anode	3026 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.032
Detector resolution: 10.0 pixels mm-1	θmax = 27.6°, θmin = 1.9°
φ and ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −10→10
Tmin = 0.553, Tmax = 0.744	l = −22→22
14803 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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0385P)2 + 0.6504P] where P = (Fo2 + 2Fc2)/3
3803 reflections	(Δ/σ)max = 0.001
227 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Br1	0.23409 (2)	0.55058 (3)	0.595181 (15)	0.04881 (10)
S1	0.40951 (4)	0.07887 (6)	0.25320 (3)	0.02349 (12)
F1	0.52925 (15)	0.6513 (2)	0.09244 (10)	0.0670 (5)
O1	0.68915 (11)	0.0164 (2)	0.42360 (8)	0.0308 (3)
O2	0.42383 (14)	−0.06341 (18)	0.20874 (9)	0.0363 (4)
O3	0.29924 (11)	0.1077 (2)	0.26702 (8)	0.0316 (3)
C1	0.51536 (16)	0.0748 (2)	0.34372 (11)	0.0240 (4)
C2	0.52174 (16)	0.1490 (3)	0.42090 (10)	0.0234 (4)
C3	0.44999 (16)	0.2428 (2)	0.45819 (10)	0.0236 (4)
C4	0.33609 (16)	0.2927 (3)	0.42204 (11)	0.0285 (4)
H4	0.3021	0.2637	0.3682	0.034*
C5	0.27304 (18)	0.3815 (3)	0.46198 (12)	0.0327 (5)
H5	0.1963	0.4132	0.4363	0.039*
C6	0.32294 (19)	0.4253 (3)	0.54121 (13)	0.0322 (5)
C7	0.43192 (19)	0.3815 (3)	0.57901 (12)	0.0329 (5)
H7	0.4638	0.4137	0.6326	0.040*
C8	0.49895 (17)	0.2882 (3)	0.53949 (11)	0.0277 (4)
C9	0.61271 (18)	0.2411 (3)	0.58063 (11)	0.0331 (5)
H9	0.6429	0.2747	0.6342	0.040*
C10	0.67917 (17)	0.1498 (3)	0.54546 (12)	0.0323 (5)
H10	0.7547	0.1165	0.5731	0.039*
C11	0.63028 (16)	0.1071 (3)	0.46594 (11)	0.0269 (4)
C12	0.61837 (17)	−0.0014 (3)	0.34912 (12)	0.0280 (4)
C13	0.6701 (2)	−0.0921 (3)	0.29391 (14)	0.0407 (6)
H13A	0.7321	−0.0267	0.2826	0.061*
H13B	0.6110	−0.1136	0.2443	0.061*
H13C	0.7014	−0.1964	0.3182	0.061*
C14	0.44463 (15)	0.2512 (3)	0.20340 (10)	0.0219 (4)
C15	0.49975 (17)	0.2294 (3)	0.14369 (11)	0.0327 (5)
H15	0.5180	0.1225	0.1292	0.039*
C16	0.5279 (2)	0.3660 (4)	0.10549 (13)	0.0423 (6)
H16	0.5651	0.3549	0.0641	0.051*
C17	0.5005 (2)	0.5172 (3)	0.12903 (14)	0.0400 (6)
C18	0.44494 (19)	0.5411 (3)	0.18684 (13)	0.0344 (5)
H18	0.4264	0.6484	0.2007	0.041*
C19	0.41645 (17)	0.4054 (3)	0.22448 (11)	0.0268 (4)
H19	0.3775	0.4180	0.2649	0.032*

	U11	U22	U33	U12	U13	U23
Br1	0.06439 (18)	0.04182 (17)	0.05384 (16)	−0.00541 (13)	0.03959 (13)	−0.00784 (12)
S1	0.0259 (2)	0.0209 (3)	0.0210 (2)	−0.00233 (19)	0.00152 (17)	−0.00073 (19)
F1	0.0806 (11)	0.0562 (11)	0.0654 (10)	−0.0212 (9)	0.0216 (9)	0.0257 (9)
O1	0.0236 (7)	0.0369 (9)	0.0295 (7)	0.0027 (6)	0.0025 (6)	0.0064 (7)
O2	0.0475 (9)	0.0228 (8)	0.0324 (7)	0.0016 (7)	0.0001 (7)	−0.0057 (7)
O3	0.0245 (7)	0.0399 (9)	0.0282 (7)	−0.0059 (7)	0.0031 (5)	0.0003 (7)
C1	0.0260 (9)	0.0230 (11)	0.0215 (8)	−0.0011 (8)	0.0035 (7)	0.0048 (8)
C2	0.0254 (9)	0.0204 (10)	0.0220 (8)	−0.0053 (8)	0.0019 (7)	0.0044 (8)
C3	0.0282 (9)	0.0200 (10)	0.0208 (8)	−0.0053 (8)	0.0034 (7)	0.0045 (8)
C4	0.0303 (10)	0.0307 (12)	0.0235 (9)	−0.0016 (9)	0.0054 (8)	0.0011 (9)
C5	0.0320 (10)	0.0350 (13)	0.0316 (10)	0.0018 (10)	0.0095 (8)	0.0037 (10)
C6	0.0453 (12)	0.0250 (12)	0.0328 (10)	−0.0040 (10)	0.0217 (9)	−0.0015 (9)
C7	0.0460 (12)	0.0310 (12)	0.0233 (9)	−0.0120 (10)	0.0116 (9)	−0.0008 (9)
C8	0.0342 (10)	0.0240 (11)	0.0235 (9)	−0.0085 (9)	0.0049 (8)	0.0018 (9)
C9	0.0374 (11)	0.0355 (13)	0.0210 (9)	−0.0114 (10)	−0.0017 (8)	0.0019 (9)
C10	0.0262 (10)	0.0376 (13)	0.0263 (9)	−0.0054 (9)	−0.0048 (8)	0.0076 (10)
C11	0.0258 (9)	0.0260 (11)	0.0269 (9)	−0.0033 (8)	0.0037 (8)	0.0058 (9)
C12	0.0286 (10)	0.0283 (11)	0.0252 (9)	−0.0005 (9)	0.0036 (8)	0.0062 (9)
C13	0.0378 (12)	0.0487 (16)	0.0375 (12)	0.0106 (11)	0.0131 (9)	0.0027 (11)
C14	0.0200 (8)	0.0243 (11)	0.0187 (8)	0.0015 (8)	0.0004 (6)	0.0014 (8)
C15	0.0360 (11)	0.0347 (13)	0.0292 (10)	0.0052 (10)	0.0116 (9)	−0.0006 (10)
C16	0.0404 (12)	0.0553 (18)	0.0359 (11)	0.0010 (12)	0.0183 (10)	0.0100 (12)
C17	0.0396 (12)	0.0381 (14)	0.0387 (12)	−0.0108 (11)	0.0040 (10)	0.0151 (11)
C18	0.0394 (12)	0.0222 (12)	0.0366 (11)	−0.0024 (10)	0.0012 (9)	0.0004 (10)
C19	0.0283 (10)	0.0259 (11)	0.0242 (9)	0.0014 (9)	0.0036 (7)	−0.0016 (9)

Br1—C6	1.900 (2)	C7—H7	0.9500
S1—O3	1.4303 (14)	C8—C9	1.421 (3)
S1—O2	1.4319 (16)	C9—C10	1.354 (3)
S1—C1	1.7487 (18)	C9—H9	0.9500
S1—C14	1.762 (2)	C10—C11	1.401 (3)
F1—C17	1.357 (3)	C10—H10	0.9500
O1—C12	1.361 (2)	C12—C13	1.477 (3)
O1—C11	1.369 (3)	C13—H13A	0.9800
C1—C12	1.368 (3)	C13—H13B	0.9800
C1—C2	1.461 (3)	C13—H13C	0.9800
C2—C11	1.378 (3)	C14—C19	1.378 (3)
C2—C3	1.433 (3)	C14—C15	1.387 (3)
C3—C4	1.410 (3)	C15—C16	1.386 (3)
C3—C8	1.434 (3)	C15—H15	0.9500
C4—C5	1.367 (3)	C16—C17	1.367 (4)
C4—H4	0.9500	C16—H16	0.9500
C5—C6	1.401 (3)	C17—C18	1.364 (3)
C5—H5	0.9500	C18—C19	1.376 (3)
C6—C7	1.352 (3)	C18—H18	0.9500
C7—C8	1.415 (3)	C19—H19	0.9500
O3—S1—O2	118.34 (10)	C9—C10—C11	116.25 (18)
O3—S1—C1	109.76 (9)	C9—C10—H10	121.9
O2—S1—C1	108.13 (9)	C11—C10—H10	121.9
O3—S1—C14	107.86 (9)	O1—C11—C2	112.00 (17)
O2—S1—C14	107.47 (9)	O1—C11—C10	121.84 (18)
C1—S1—C14	104.37 (9)	C2—C11—C10	126.2 (2)
C12—O1—C11	106.89 (15)	O1—C12—C1	110.17 (18)
C12—C1—C2	107.40 (16)	O1—C12—C13	114.29 (17)
C12—C1—S1	120.12 (15)	C1—C12—C13	135.52 (19)
C2—C1—S1	132.37 (15)	C12—C13—H13A	109.5
C11—C2—C3	117.91 (17)	C12—C13—H13B	109.5
C11—C2—C1	103.54 (17)	H13A—C13—H13B	109.5
C3—C2—C1	138.54 (17)	C12—C13—H13C	109.5
C4—C3—C2	125.66 (17)	H13A—C13—H13C	109.5
C4—C3—C8	117.73 (18)	H13B—C13—H13C	109.5
C2—C3—C8	116.61 (17)	C19—C14—C15	121.19 (19)
C5—C4—C3	122.05 (18)	C19—C14—S1	119.23 (14)
C5—C4—H4	119.0	C15—C14—S1	119.57 (17)
C3—C4—H4	119.0	C16—C15—C14	119.0 (2)
C4—C5—C6	119.2 (2)	C16—C15—H15	120.5
C4—C5—H5	120.4	C14—C15—H15	120.5
C6—C5—H5	120.4	C17—C16—C15	118.1 (2)
C7—C6—C5	121.5 (2)	C17—C16—H16	120.9
C7—C6—Br1	120.08 (16)	C15—C16—H16	120.9
C5—C6—Br1	118.42 (17)	F1—C17—C18	117.9 (2)
C6—C7—C8	120.63 (19)	F1—C17—C16	118.3 (2)
C6—C7—H7	119.7	C18—C17—C16	123.8 (2)
C8—C7—H7	119.7	C17—C18—C19	118.1 (2)
C7—C8—C9	119.80 (18)	C17—C18—H18	121.0
C7—C8—C3	118.90 (18)	C19—C18—H18	121.0
C9—C8—C3	121.30 (19)	C18—C19—C14	119.79 (19)
C10—C9—C8	121.73 (18)	C18—C19—H19	120.1
C10—C9—H9	119.1	C14—C19—H19	120.1
C8—C9—H9	119.1
O3—S1—C1—C12	158.70 (17)	C12—O1—C11—C2	0.2 (2)
O2—S1—C1—C12	28.3 (2)	C12—O1—C11—C10	−179.3 (2)
C14—S1—C1—C12	−85.93 (18)	C3—C2—C11—O1	179.30 (17)
O3—S1—C1—C2	−25.7 (2)	C1—C2—C11—O1	0.2 (2)
O2—S1—C1—C2	−156.10 (19)	C3—C2—C11—C10	−1.1 (3)
C14—S1—C1—C2	89.7 (2)	C1—C2—C11—C10	179.8 (2)
C12—C1—C2—C11	−0.6 (2)	C9—C10—C11—O1	179.38 (19)
S1—C1—C2—C11	−176.64 (17)	C9—C10—C11—C2	−0.1 (3)
C12—C1—C2—C3	−179.4 (2)	C11—O1—C12—C1	−0.7 (2)
S1—C1—C2—C3	4.6 (4)	C11—O1—C12—C13	177.91 (19)
C11—C2—C3—C4	−178.3 (2)	C2—C1—C12—O1	0.8 (2)
C1—C2—C3—C4	0.4 (4)	S1—C1—C12—O1	177.41 (14)
C11—C2—C3—C8	1.3 (3)	C2—C1—C12—C13	−177.3 (3)
C1—C2—C3—C8	180.0 (2)	S1—C1—C12—C13	−0.7 (4)
C2—C3—C4—C5	179.7 (2)	O3—S1—C14—C19	38.53 (17)
C8—C3—C4—C5	0.1 (3)	O2—S1—C14—C19	167.16 (15)
C3—C4—C5—C6	0.3 (3)	C1—S1—C14—C19	−78.17 (16)
C4—C5—C6—C7	−0.1 (3)	O3—S1—C14—C15	−141.32 (15)
C4—C5—C6—Br1	179.40 (17)	O2—S1—C14—C15	−12.69 (18)
C5—C6—C7—C8	−0.6 (3)	C1—S1—C14—C15	101.98 (16)
Br1—C6—C7—C8	179.98 (16)	C19—C14—C15—C16	0.7 (3)
C6—C7—C8—C9	−179.0 (2)	S1—C14—C15—C16	−179.40 (16)
C6—C7—C8—C3	0.9 (3)	C14—C15—C16—C17	0.5 (3)
C4—C3—C8—C7	−0.7 (3)	C15—C16—C17—F1	179.2 (2)
C2—C3—C8—C7	179.70 (18)	C15—C16—C17—C18	−1.5 (4)
C4—C3—C8—C9	179.25 (19)	F1—C17—C18—C19	−179.53 (19)
C2—C3—C8—C9	−0.4 (3)	C16—C17—C18—C19	1.1 (3)
C7—C8—C9—C10	179.0 (2)	C17—C18—C19—C14	0.2 (3)
C3—C8—C9—C10	−0.9 (3)	C15—C14—C19—C18	−1.1 (3)
C8—C9—C10—C11	1.2 (3)	S1—C14—C19—C18	179.04 (15)

Cg1 is the centroid of the C14–C19 4-fluorophenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2i	0.95	2.57	3.312 (3)	135.
C18—H18···O2ii	0.95	2.36	3.266 (3)	160.
C19—H19···O3i	0.95	2.57	3.113 (2)	117.
C10—H10···Cg1iii	0.95	2.69	3.609 (2)	152.

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C14–C19 4-fluoro­phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2i	0.95	2.57	3.312 (3)	135
C18—H18⋯O2ii	0.95	2.36	3.266 (3)	160
C19—H19⋯O3i	0.95	2.57	3.113 (2)	117
C10—H10⋯Cg1iii	0.95	2.69	3.609 (2)	152

Symmetry codes: (i) ; (ii) ; (iii) .