7-Bromo-1-(4-chloro-phenyl-sulfan-yl)-2-phenyl-naphtho[2,1-b]furan.

In the title compound, C(24)H(14)BrClOS, the S-bound 4-chloro-phenyl ring is nearly perpendicular to the plane of the naphthofuran fragment [dihedral angle = 83.34 (3)°] and the phenyl ring in the 2-position is rotated out of the naphthofuran plane by a dihedral angle of 15.23 (5)°. The crystal structure is stabilized by aromatic π-π inter-actions between the furan and the central benzene rings of the neighbouring naphthofuran fragments, and between the outer benzene rings of the neighbouring naphthofuran fragments; the centroid-centroid distances within the stack are 3.879 (2) and 3.857 (2) Å. In addition, inter-molecular C-Cl⋯π inter-actions [3.505 (2) Å] between the Cl atom and the 2-phenyl ring are present.

Related literature

For the crystal structures of similar 7-bromo-2-phenyl­naphtho[2,1-b]furan derivatives, see: Choi et al. (2009a ▶,b ▶). For the biological activity of naphthofuran compounds, see: Hagiwara et al. (1999 ▶); Hranjec et al. (2003 ▶); Mahadevan & Vaidya (2003 ▶).

Experimental

Crystal data

C24H14BrClOS

M = 465.77

Triclinic,

a = 8.2479 (3) Å

b = 8.3136 (4) Å

c = 13.9805 (6) Å

α = 93.530 (2)°

β = 99.317 (2)°

γ = 90.342 (2)°

V = 944.07 (7) Å3

Z = 2

Mo Kα radiation

μ = 2.44 mm−1

T = 173 K

0.40 × 0.20 × 0.05 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.560, T max = 0.887

16830 measured reflections

4364 independent reflections

3912 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.068

S = 1.05

4364 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.33 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/S1600536809052945/bg2314sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052945/bg2314Isup2.hkl

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

C24H14BrClOS	Z = 2
Mr = 465.77	F(000) = 468
Triclinic, P1	Dx = 1.639 Mg m−3
Hall symbol: -p 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2479 (3) Å	Cell parameters from 2528 reflections
b = 8.3136 (4) Å	θ = 2.3–25.7°
c = 13.9805 (6) Å	µ = 2.44 mm−1
α = 93.530 (2)°	T = 173 K
β = 99.317 (2)°	Block, colourless
γ = 90.342 (2)°	0.40 × 0.20 × 0.05 mm
V = 944.07 (7) Å3

Bruker SMART APEXII CCD diffractometer	4364 independent reflections
Radiation source: Rotating Anode	3912 reflections with I > 2σ(I)
HELIOS	Rint = 0.024
Detector resolution: 10.0 pixels mm-1	θmax = 27.6°, θmin = 1.5°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −10→10
Tmin = 0.560, Tmax = 0.887	l = −18→18
16830 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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0368P)2 + 0.2823P] where P = (Fo2 + 2Fc2)/3
4364 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.33 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
Br	0.16900 (2)	−0.00651 (2)	0.696104 (13)	0.03934 (7)
S	0.32781 (5)	0.41585 (5)	0.26003 (3)	0.02372 (9)
Cl	0.23890 (5)	−0.23943 (5)	0.00792 (3)	0.03551 (11)
O	0.79044 (13)	0.43650 (13)	0.39137 (8)	0.0236 (2)
C1	0.52090 (18)	0.40291 (18)	0.33320 (11)	0.0215 (3)
C2	0.55319 (19)	0.33416 (17)	0.42666 (11)	0.0220 (3)
C3	0.45931 (19)	0.25242 (17)	0.48592 (11)	0.0226 (3)
C4	0.2890 (2)	0.21797 (19)	0.46150 (12)	0.0271 (3)
H4	0.2308	0.2497	0.4015	0.033*
C6	0.2914 (2)	0.09476 (19)	0.61175 (12)	0.0292 (3)
C7	0.4563 (2)	0.12282 (19)	0.63870 (12)	0.0286 (3)
H7	0.5114	0.0886	0.6989	0.034*
C8	0.5445 (2)	0.20304 (18)	0.57655 (11)	0.0252 (3)
C9	0.7169 (2)	0.2345 (2)	0.60430 (11)	0.0282 (3)
H9	0.7712	0.1995	0.6645	0.034*
C10	0.8055 (2)	0.3132 (2)	0.54683 (11)	0.0267 (3)
H10	0.9197	0.3355	0.5659	0.032*
C5	0.2067 (2)	0.1400 (2)	0.52255 (13)	0.0295 (3)
H5	0.0926	0.1165	0.5047	0.035*
C11	0.71960 (19)	0.35948 (18)	0.45816 (11)	0.0232 (3)
C12	0.66752 (19)	0.46116 (18)	0.31452 (11)	0.0225 (3)
C13	0.72391 (19)	0.52879 (18)	0.23142 (11)	0.0227 (3)
C14	0.6152 (2)	0.5820 (2)	0.15241 (12)	0.0294 (3)
H14	0.5004	0.5809	0.1537	0.035*
C15	0.6734 (2)	0.6363 (2)	0.07257 (12)	0.0304 (4)
H15	0.5982	0.6708	0.0192	0.037*
C16	0.8403 (2)	0.6409 (2)	0.06961 (12)	0.0289 (3)
H16	0.8797	0.6781	0.0146	0.035*
C17	0.9493 (2)	0.5907 (2)	0.14774 (13)	0.0324 (4)
H17	1.0641	0.5944	0.1464	0.039*
C18	0.8923 (2)	0.5350 (2)	0.22773 (12)	0.0281 (3)
H18	0.9685	0.5007	0.2807	0.034*
C19	0.30880 (19)	0.22538 (18)	0.19376 (11)	0.0219 (3)
C20	0.1534 (2)	0.1543 (2)	0.16982 (12)	0.0271 (3)
H20	0.0622	0.2044	0.1923	0.033*
C21	0.1313 (2)	0.0107 (2)	0.11338 (12)	0.0295 (3)
H21	0.0251	−0.0377	0.0965	0.035*
C22	0.2658 (2)	−0.06179 (19)	0.08176 (11)	0.0257 (3)
C23	0.4219 (2)	0.0055 (2)	0.10721 (11)	0.0255 (3)
H23	0.5135	−0.0471	0.0868	0.031*
C24	0.44322 (19)	0.15046 (19)	0.16274 (11)	0.0241 (3)
H24	0.5496	0.1986	0.1796	0.029*

	U11	U22	U33	U12	U13	U23
Br	0.04043 (12)	0.04369 (12)	0.03854 (11)	−0.00180 (8)	0.01701 (8)	0.01182 (8)
S	0.02033 (18)	0.02376 (19)	0.02618 (19)	0.00233 (14)	0.00094 (14)	0.00188 (14)
Cl	0.0318 (2)	0.0343 (2)	0.0391 (2)	−0.00495 (17)	0.00692 (18)	−0.01079 (17)
O	0.0224 (5)	0.0263 (6)	0.0215 (5)	−0.0027 (4)	0.0017 (4)	0.0017 (4)
C1	0.0211 (7)	0.0209 (7)	0.0220 (7)	0.0008 (6)	0.0022 (6)	0.0002 (5)
C2	0.0248 (8)	0.0188 (7)	0.0218 (7)	0.0015 (6)	0.0027 (6)	−0.0015 (5)
C3	0.0267 (8)	0.0178 (7)	0.0235 (7)	0.0013 (6)	0.0060 (6)	−0.0014 (5)
C4	0.0266 (8)	0.0278 (8)	0.0269 (8)	0.0012 (6)	0.0043 (6)	0.0025 (6)
C6	0.0369 (9)	0.0229 (8)	0.0310 (8)	0.0010 (7)	0.0145 (7)	0.0022 (6)
C7	0.0366 (9)	0.0261 (8)	0.0244 (8)	0.0021 (7)	0.0082 (7)	0.0027 (6)
C8	0.0317 (8)	0.0211 (7)	0.0233 (7)	0.0022 (6)	0.0061 (6)	−0.0002 (6)
C9	0.0331 (9)	0.0291 (8)	0.0211 (7)	0.0020 (7)	0.0006 (6)	0.0015 (6)
C10	0.0266 (8)	0.0290 (8)	0.0226 (7)	0.0003 (6)	−0.0006 (6)	−0.0008 (6)
C5	0.0272 (8)	0.0284 (8)	0.0343 (9)	−0.0007 (7)	0.0090 (7)	0.0020 (7)
C11	0.0265 (8)	0.0213 (7)	0.0215 (7)	−0.0006 (6)	0.0040 (6)	−0.0010 (6)
C12	0.0233 (7)	0.0206 (7)	0.0222 (7)	0.0006 (6)	0.0002 (6)	−0.0008 (6)
C13	0.0247 (8)	0.0185 (7)	0.0247 (7)	−0.0009 (6)	0.0038 (6)	0.0002 (6)
C14	0.0228 (8)	0.0340 (9)	0.0319 (8)	0.0010 (7)	0.0035 (7)	0.0073 (7)
C15	0.0311 (9)	0.0308 (9)	0.0289 (8)	0.0011 (7)	0.0012 (7)	0.0086 (7)
C16	0.0317 (9)	0.0289 (8)	0.0272 (8)	−0.0033 (7)	0.0069 (7)	0.0057 (6)
C17	0.0240 (8)	0.0412 (10)	0.0325 (9)	−0.0022 (7)	0.0051 (7)	0.0056 (7)
C18	0.0235 (8)	0.0341 (9)	0.0260 (8)	−0.0004 (6)	0.0007 (6)	0.0048 (6)
C19	0.0225 (7)	0.0245 (7)	0.0185 (7)	−0.0001 (6)	0.0026 (6)	0.0036 (5)
C20	0.0230 (8)	0.0324 (9)	0.0267 (8)	−0.0009 (6)	0.0070 (6)	0.0007 (6)
C21	0.0222 (8)	0.0349 (9)	0.0307 (8)	−0.0053 (7)	0.0043 (6)	−0.0019 (7)
C22	0.0285 (8)	0.0261 (8)	0.0223 (7)	−0.0025 (6)	0.0043 (6)	−0.0003 (6)
C23	0.0237 (8)	0.0301 (8)	0.0232 (7)	0.0014 (6)	0.0058 (6)	0.0021 (6)
C24	0.0210 (7)	0.0280 (8)	0.0230 (7)	−0.0014 (6)	0.0022 (6)	0.0029 (6)

Br—C6	1.902 (2)	C5—H5	0.9500
S—C1	1.756 (2)	C12—C13	1.461 (2)
S—C19	1.778 (2)	C13—C18	1.399 (2)
Cl—C22	1.741 (2)	C13—C14	1.402 (2)
O—C11	1.367 (2)	C14—C15	1.383 (2)
O—C12	1.379 (2)	C14—H14	0.9500
C1—C12	1.370 (2)	C15—C16	1.384 (2)
C1—C2	1.444 (2)	C15—H15	0.9500
C2—C11	1.383 (2)	C16—C17	1.385 (2)
C2—C3	1.421 (2)	C16—H16	0.9500
C3—C4	1.414 (2)	C17—C18	1.385 (2)
C3—C8	1.431 (2)	C17—H17	0.9500
C4—C5	1.363 (2)	C18—H18	0.9500
C4—H4	0.9500	C19—C20	1.390 (2)
C6—C7	1.366 (2)	C19—C24	1.391 (2)
C6—C5	1.401 (2)	C20—C21	1.384 (2)
C7—C8	1.414 (2)	C20—H20	0.9500
C7—H7	0.9500	C21—C22	1.387 (2)
C8—C9	1.430 (2)	C21—H21	0.9500
C9—C10	1.363 (2)	C22—C23	1.384 (2)
C9—H9	0.9500	C23—C24	1.387 (2)
C10—C11	1.402 (2)	C23—H23	0.9500
C10—H10	0.9500	C24—H24	0.9500
C1—S—C19	102.09 (7)	O—C12—C13	114.55 (13)
C11—O—C12	106.90 (12)	C18—C13—C14	118.09 (15)
C12—C1—C2	107.21 (13)	C18—C13—C12	119.32 (14)
C12—C1—S	126.72 (12)	C14—C13—C12	122.53 (14)
C2—C1—S	126.02 (12)	C15—C14—C13	120.62 (15)
C11—C2—C3	119.11 (14)	C15—C14—H14	119.7
C11—C2—C1	104.92 (14)	C13—C14—H14	119.7
C3—C2—C1	135.96 (14)	C14—C15—C16	120.68 (15)
C4—C3—C2	124.52 (14)	C14—C15—H15	119.7
C4—C3—C8	118.44 (15)	C16—C15—H15	119.7
C2—C3—C8	117.04 (14)	C15—C16—C17	119.32 (16)
C5—C4—C3	121.19 (15)	C15—C16—H16	120.3
C5—C4—H4	119.4	C17—C16—H16	120.3
C3—C4—H4	119.4	C18—C17—C16	120.50 (16)
C7—C6—C5	121.77 (16)	C18—C17—H17	119.7
C7—C6—Br	120.34 (13)	C16—C17—H17	119.7
C5—C6—Br	117.89 (13)	C17—C18—C13	120.78 (15)
C6—C7—C8	119.65 (15)	C17—C18—H18	119.6
C6—C7—H7	120.2	C13—C18—H18	119.6
C8—C7—H7	120.2	C20—C19—C24	120.00 (15)
C7—C8—C9	120.21 (15)	C20—C19—S	118.20 (12)
C7—C8—C3	119.26 (15)	C24—C19—S	121.76 (12)
C9—C8—C3	120.53 (15)	C21—C20—C19	120.17 (15)
C10—C9—C8	121.84 (15)	C21—C20—H20	119.9
C10—C9—H9	119.1	C19—C20—H20	119.9
C8—C9—H9	119.1	C20—C21—C22	119.34 (15)
C9—C10—C11	116.57 (15)	C20—C21—H21	120.3
C9—C10—H10	121.7	C22—C21—H21	120.3
C11—C10—H10	121.7	C23—C22—C21	121.09 (15)
C4—C5—C6	119.68 (16)	C23—C22—Cl	119.07 (12)
C4—C5—H5	120.2	C21—C22—Cl	119.84 (12)
C6—C5—H5	120.2	C22—C23—C24	119.38 (15)
O—C11—C2	111.08 (13)	C22—C23—H23	120.3
O—C11—C10	124.03 (14)	C24—C23—H23	120.3
C2—C11—C10	124.88 (15)	C23—C24—C19	119.98 (14)
C1—C12—O	109.87 (13)	C23—C24—H24	120.0
C1—C12—C13	135.35 (14)	C19—C24—H24	120.0
C19—S—C1—C12	96.64 (14)	C9—C10—C11—O	−178.71 (14)
C19—S—C1—C2	−86.08 (14)	C9—C10—C11—C2	1.5 (2)
C12—C1—C2—C11	1.00 (17)	C2—C1—C12—O	−1.22 (17)
S—C1—C2—C11	−176.71 (11)	S—C1—C12—O	176.48 (10)
C12—C1—C2—C3	−177.97 (16)	C2—C1—C12—C13	172.70 (16)
S—C1—C2—C3	4.3 (3)	S—C1—C12—C13	−9.6 (3)
C11—C2—C3—C4	−179.42 (14)	C11—O—C12—C1	0.94 (16)
C1—C2—C3—C4	−0.6 (3)	C11—O—C12—C13	−174.37 (12)
C11—C2—C3—C8	0.9 (2)	C1—C12—C13—C18	−162.13 (17)
C1—C2—C3—C8	179.78 (16)	O—C12—C13—C18	11.6 (2)
C2—C3—C4—C5	−179.47 (15)	C1—C12—C13—C14	15.1 (3)
C8—C3—C4—C5	0.2 (2)	O—C12—C13—C14	−171.21 (14)
C5—C6—C7—C8	1.5 (2)	C18—C13—C14—C15	1.2 (2)
Br—C6—C7—C8	−177.91 (11)	C12—C13—C14—C15	−176.09 (15)
C6—C7—C8—C9	179.43 (15)	C13—C14—C15—C16	−0.8 (3)
C6—C7—C8—C3	−0.5 (2)	C14—C15—C16—C17	−0.1 (3)
C4—C3—C8—C7	−0.4 (2)	C15—C16—C17—C18	0.6 (3)
C2—C3—C8—C7	179.30 (13)	C16—C17—C18—C13	−0.2 (3)
C4—C3—C8—C9	179.72 (14)	C14—C13—C18—C17	−0.7 (2)
C2—C3—C8—C9	−0.6 (2)	C12—C13—C18—C17	176.65 (15)
C7—C8—C9—C10	−179.19 (15)	C1—S—C19—C20	145.84 (13)
C3—C8—C9—C10	0.7 (2)	C1—S—C19—C24	−36.64 (14)
C8—C9—C10—C11	−1.1 (2)	C24—C19—C20—C21	−1.4 (2)
C3—C4—C5—C6	0.8 (2)	S—C19—C20—C21	176.17 (13)
C7—C6—C5—C4	−1.7 (3)	C19—C20—C21—C22	0.5 (3)
Br—C6—C5—C4	177.73 (12)	C20—C21—C22—C23	1.2 (3)
C12—O—C11—C2	−0.27 (16)	C20—C21—C22—Cl	−178.21 (13)
C12—O—C11—C10	179.87 (14)	C21—C22—C23—C24	−2.0 (2)
C3—C2—C11—O	178.73 (12)	Cl—C22—C23—C24	177.39 (12)
C1—C2—C11—O	−0.45 (17)	C22—C23—C24—C19	1.1 (2)
C3—C2—C11—C10	−1.4 (2)	C20—C19—C24—C23	0.6 (2)
C1—C2—C11—C10	179.41 (14)	S—C19—C24—C23	−176.92 (12)