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The title compound, C19H13BrOS, was prepared by the Lewis acid-catalyzed reaction of 6-bromo-2-naphthol and α-chloro-α-(phenyl­sulfan­yl)acetone. There are two symmetry-independent mol­ecules in the asymmetric unit. The phenyl rings are nearly perpendicular to the naphthofuran systems, with dihedral angles of 72.9 (1) and 80.5 (1)°. The crystal structure is stabilized by π–π stacking inter­actions between the brominated benzene ring and the furan fragment of the naphthofuran system from two symmetry-independent mol­ecules; the centroid-to-centroid distances within the stack are 3.594 (9) and 3.658 (9) Å. Additionally, the stacked mol­ecules exhibit short C—H...π contacts between the methyl H atoms and the central benzene ring of the naphthofuran system.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680704562X/gk2104sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680704562X/gk2104Isup2.hkl
Contains datablock I

CCDC reference: 663797

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.058
  • wR factor = 0.152
  • Data-to-parameter ratio = 13.1

checkCIF/PLATON results

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Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.48 PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 200 Ang. PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 9
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

As part of our ongoing studies on the synthesis and structure of 2-methylnaphtho[2,1-b]furan analogues, we have recently described the crystal structures of 2-methyl-1-(methylsulfinyl)naphtho[2,1-b]furan (Choi et al., 2006) and 2-methyl-1-(phenylsulfinyl)naphtho[2,1-b]furan (Choi et al., 2007). Herein we report the molecular and crystal structure of the title compound, (Fig. 1).

The phenyl rings (C13—C18 in unit A and C32—C37 in unit B) are tilted towards the plane of the naphthofuran systems [72.9 (9)° (unit A) and 80.5 (1)° (unit B)]. The molecular packing (Fig. 2) is stabilized by two different π···π interactions within each stack of molecules; one between the benzene ring (Cg4) and an adjacent furan ring (Cg1) of benzofuran unit {distance; 3.594 (9) Å}, and a second between the benzene ring (Cg6) and an adjacent furan ring (Cg2) of benzofuran unit {distance; 3.658 (9) Å} (Cg1, Cg2, Cg4, and Cg6 are the centroids of the O1/C12/C1/C2/C11 furan ring, the O2/C31/C20/C21/C30 furan ring, the C22—C27 benzene ring, and the C3—C8 benzene ring, respectively; symmetry code as in Fig. 2). The crystal packing (Fig. 2) is further stabilized by CH2—H···π interactions; one between the methyl group (unit B) and the benzene ring (unit A) of benzofuran unit, with a C38—H38A···Cg5 separation of 2.60 Å, and a second between the methyl group (Unit A) and the benzene ring (Unit B) of benzofuran unit, with a C19—H19C···Cg3 separation of 2.77 Å (Fig. 2 and Table 1; Cg3 and Cg5 are the centroids of the C21/C22/C27/C28/C29/C30 benzene ring and the C2/C3/C8/C9/C10/C11 benzene ring, respectively; symmetry code as in Fig. 2). In addition, the crystal packing (Fig. 2) is further stabilized by weak C—Br···π interactions: one between the Br atom (Unit B) and the phenyl ring (Unit A) with a C25—Br2···Cg8 separation of 3.718 (6) Å, and a second between the Br atom (Unit A) and the phenyl ring (Unit B) with a C6—Br1···Cg7 separation of 4.015 (6) Å (Fig. 2; Cg7 and Cg8 are the centroids of the C32—C37 benzene ring and the C13—C18 benzene ring, respectively; symmetry code as in Fig. 2).

Related literature top

For the crystal structures of similar naphthofuran compounds, see: Choi et al. (2006, 2007).

Experimental top

Zinc chloride (273 mg, 2.0 mmol) was added at room temperature to a stirred solution of 6-bromo-2-naphthol (446 mg, 2.0 mmol) and α-chloro-α-(phenylsulfanyl)acetone (401 mg, 2.0 mmol) in dichloromethane (30 ml), and stirred for 1 h. The mixture was quenched with water and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by column chromatography (CCl4) to afford the title compound as a colorless solid [yield 63%, m.p. 436–437 K; Rf = 0.68 (CCl4)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a dilute solution of the title compound in chloroform at room temperature.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å for aromatic H atoms and 0.98 Å for methyl H atoms, respectively, and with Uiso(H) = 1.2Ueq(C) for aromatic H atoms and Uiso(H) = 1.5Ueq(C) for methyl H atoms. The highest peak in the difference map is 1.13 Å from Br2 and the largest hole is 0.88 Å from Br1.

Structure description top

As part of our ongoing studies on the synthesis and structure of 2-methylnaphtho[2,1-b]furan analogues, we have recently described the crystal structures of 2-methyl-1-(methylsulfinyl)naphtho[2,1-b]furan (Choi et al., 2006) and 2-methyl-1-(phenylsulfinyl)naphtho[2,1-b]furan (Choi et al., 2007). Herein we report the molecular and crystal structure of the title compound, (Fig. 1).

The phenyl rings (C13—C18 in unit A and C32—C37 in unit B) are tilted towards the plane of the naphthofuran systems [72.9 (9)° (unit A) and 80.5 (1)° (unit B)]. The molecular packing (Fig. 2) is stabilized by two different π···π interactions within each stack of molecules; one between the benzene ring (Cg4) and an adjacent furan ring (Cg1) of benzofuran unit {distance; 3.594 (9) Å}, and a second between the benzene ring (Cg6) and an adjacent furan ring (Cg2) of benzofuran unit {distance; 3.658 (9) Å} (Cg1, Cg2, Cg4, and Cg6 are the centroids of the O1/C12/C1/C2/C11 furan ring, the O2/C31/C20/C21/C30 furan ring, the C22—C27 benzene ring, and the C3—C8 benzene ring, respectively; symmetry code as in Fig. 2). The crystal packing (Fig. 2) is further stabilized by CH2—H···π interactions; one between the methyl group (unit B) and the benzene ring (unit A) of benzofuran unit, with a C38—H38A···Cg5 separation of 2.60 Å, and a second between the methyl group (Unit A) and the benzene ring (Unit B) of benzofuran unit, with a C19—H19C···Cg3 separation of 2.77 Å (Fig. 2 and Table 1; Cg3 and Cg5 are the centroids of the C21/C22/C27/C28/C29/C30 benzene ring and the C2/C3/C8/C9/C10/C11 benzene ring, respectively; symmetry code as in Fig. 2). In addition, the crystal packing (Fig. 2) is further stabilized by weak C—Br···π interactions: one between the Br atom (Unit B) and the phenyl ring (Unit A) with a C25—Br2···Cg8 separation of 3.718 (6) Å, and a second between the Br atom (Unit A) and the phenyl ring (Unit B) with a C6—Br1···Cg7 separation of 4.015 (6) Å (Fig. 2; Cg7 and Cg8 are the centroids of the C32—C37 benzene ring and the C13—C18 benzene ring, respectively; symmetry code as in Fig. 2).

For the crystal structures of similar naphthofuran compounds, see: Choi et al. (2006, 2007).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing displacement ellipsoides drawn at the 50% probability level.
[Figure 2] Fig. 2. π···π, C—H···π and C—-Br···π intreactions (dotted lines) in the title compound. Cg denotes ring centroids. [Symmetry code: (i) x, 1 + y, z; (ii) -x, 1 - y, 2 - z; (iii) 1 - x, 1 - y, 2 - z.]
7-Bromo-2-methyl-1-(phenylsulfanyl)naphtho[2,1-b]furan top
Crystal data top
C19H13BrOSZ = 4
Mr = 369.26F(000) = 744
Triclinic, P1Dx = 1.603 Mg m3
Hall symbol: -p 1Mo Kα radiation, λ = 0.71073 Å
a = 10.947 (2) ÅCell parameters from 4034 reflections
b = 11.130 (2) Åθ = 2.4–28.1°
c = 13.636 (2) ŵ = 2.82 mm1
α = 112.798 (2)°T = 173 K
β = 91.999 (3)°Plate, colorless
γ = 90.908 (2)°0.35 × 0.25 × 0.10 mm
V = 1529.9 (5) Å3
Data collection top
Bruker SMART CCD
diffractometer
5209 independent reflections
Radiation source: fine-focus sealed tube4269 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
Detector resolution: 10.00 pixels mm-1θmax = 25.0°, θmin = 1.9°
φ and ω scansh = 1213
Absorption correction: multi-scan
(SADABS; Sheldrick, 1999)
k = 1313
Tmin = 0.442, Tmax = 0.760l = 616
7613 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H-atom parameters constrained
S = 1.14 w = 1/[σ2(Fo2) + (0.0494P)2 + 8.0396P]
where P = (Fo2 + 2Fc2)/3
5209 reflections(Δ/σ)max < 0.001
398 parametersΔρmax = 1.62 e Å3
0 restraintsΔρmin = 0.65 e Å3
Crystal data top
C19H13BrOSγ = 90.908 (2)°
Mr = 369.26V = 1529.9 (5) Å3
Triclinic, P1Z = 4
a = 10.947 (2) ÅMo Kα radiation
b = 11.130 (2) ŵ = 2.82 mm1
c = 13.636 (2) ÅT = 173 K
α = 112.798 (2)°0.35 × 0.25 × 0.10 mm
β = 91.999 (3)°
Data collection top
Bruker SMART CCD
diffractometer
5209 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1999)
4269 reflections with I > 2σ(I)
Tmin = 0.442, Tmax = 0.760Rint = 0.025
7613 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0580 restraints
wR(F2) = 0.152H-atom parameters constrained
S = 1.14Δρmax = 1.62 e Å3
5209 reflectionsΔρmin = 0.65 e Å3
398 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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
xyzUiso*/Ueq
Br10.30246 (6)0.23787 (6)1.08462 (5)0.0340 (2)
Br20.21489 (7)0.73817 (6)1.09288 (5)0.0372 (2)
S10.03179 (14)0.56857 (14)0.75823 (13)0.0264 (3)
S20.49841 (14)1.06833 (14)0.75250 (13)0.0271 (3)
O10.2948 (4)0.5907 (4)0.6588 (3)0.0273 (9)
O20.1570 (4)1.0853 (4)0.6640 (3)0.0286 (10)
C10.1213 (6)0.5505 (5)0.7258 (5)0.0243 (13)
C20.2219 (5)0.5038 (5)0.7717 (5)0.0232 (12)
C30.2368 (5)0.4429 (5)0.8456 (5)0.0252 (13)
C40.1379 (5)0.4037 (6)0.8922 (5)0.0267 (13)
H40.05650.41960.87500.032*
C50.1577 (6)0.3435 (6)0.9615 (5)0.0304 (14)
H50.09060.31710.99170.036*
C60.2774 (6)0.3212 (6)0.9875 (5)0.0276 (13)
C70.3755 (6)0.3548 (6)0.9445 (5)0.0293 (14)
H70.45570.33700.96290.035*
C80.3579 (5)0.4172 (6)0.8714 (5)0.0256 (13)
C90.4605 (6)0.4532 (6)0.8254 (5)0.0288 (14)
H90.54070.43650.84460.035*
C100.4449 (6)0.5118 (6)0.7538 (5)0.0316 (14)
H100.51260.53650.72320.038*
C110.3257 (6)0.5329 (5)0.7284 (5)0.0253 (13)
C120.1696 (6)0.5981 (6)0.6569 (5)0.0270 (13)
C130.1025 (5)0.4098 (6)0.6961 (5)0.0235 (12)
C140.2286 (6)0.4044 (6)0.7031 (5)0.0302 (14)
H140.27120.48140.74030.036*
C150.2910 (6)0.2868 (7)0.6559 (6)0.0377 (16)
H150.37720.28310.66070.045*
C160.2308 (6)0.1740 (6)0.6014 (5)0.0367 (16)
H160.27490.09310.56890.044*
C170.1065 (7)0.1805 (6)0.5950 (5)0.0353 (16)
H170.06460.10320.55680.042*
C180.0398 (6)0.2987 (6)0.6434 (5)0.0319 (15)
H180.04670.30200.63990.038*
C190.1166 (6)0.6575 (6)0.5860 (5)0.0348 (15)
H19A0.02720.64970.58440.052*
H19B0.14540.61240.51400.052*
H19C0.14210.74980.61270.052*
C200.3396 (5)1.0475 (5)0.7246 (5)0.0228 (12)
C210.2475 (5)0.9976 (5)0.7729 (5)0.0254 (13)
C220.2450 (5)0.9334 (5)0.8445 (5)0.0242 (13)
C230.3499 (6)0.8997 (6)0.8901 (5)0.0300 (14)
H230.42840.91780.87050.036*
C240.3419 (6)0.8417 (6)0.9618 (5)0.0314 (14)
H240.41370.81870.99090.038*
C250.2254 (6)0.8166 (6)0.9917 (5)0.0285 (14)
C260.1205 (6)0.8471 (6)0.9498 (5)0.0308 (14)
H260.04310.82900.97130.037*
C270.1272 (6)0.9054 (6)0.8748 (5)0.0269 (13)
C280.0182 (6)0.9375 (6)0.8317 (6)0.0341 (15)
H280.05880.91820.85320.041*
C290.0217 (6)0.9958 (6)0.7599 (5)0.0320 (15)
H290.05091.01630.73020.038*
C300.1372 (6)1.0235 (6)0.7324 (5)0.0293 (14)
C310.2818 (6)1.0986 (6)0.6610 (5)0.0262 (13)
C320.5543 (5)0.9086 (6)0.6865 (5)0.0251 (13)
C330.6747 (6)0.8905 (7)0.7109 (5)0.0346 (15)
H330.72200.96070.76200.041*
C340.7264 (6)0.7704 (7)0.6608 (6)0.0371 (16)
H340.80910.75860.67800.045*
C350.6599 (7)0.6687 (6)0.5871 (6)0.0372 (16)
H350.69580.58650.55300.045*
C360.5391 (7)0.6866 (6)0.5625 (6)0.0372 (16)
H360.49270.61630.51080.045*
C370.4854 (6)0.8059 (6)0.6127 (5)0.0306 (14)
H370.40220.81700.59650.037*
C380.3258 (6)1.1671 (6)0.5937 (5)0.0328 (15)
H38A0.31821.26140.63170.049*
H38B0.27641.13760.52680.049*
H38C0.41161.14750.57840.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0461 (4)0.0292 (3)0.0315 (4)0.0040 (3)0.0021 (3)0.0168 (3)
Br20.0543 (5)0.0316 (4)0.0308 (4)0.0065 (3)0.0025 (3)0.0180 (3)
S10.0264 (8)0.0206 (7)0.0322 (9)0.0028 (6)0.0041 (6)0.0099 (6)
S20.0259 (8)0.0203 (7)0.0341 (9)0.0029 (6)0.0014 (6)0.0096 (6)
O10.033 (2)0.026 (2)0.026 (2)0.0006 (17)0.0070 (18)0.0125 (18)
O20.032 (2)0.027 (2)0.031 (2)0.0031 (18)0.0012 (18)0.0158 (19)
C10.038 (3)0.012 (3)0.022 (3)0.004 (2)0.002 (3)0.007 (2)
C20.028 (3)0.017 (3)0.023 (3)0.000 (2)0.006 (2)0.006 (2)
C30.028 (3)0.020 (3)0.021 (3)0.004 (2)0.001 (2)0.002 (2)
C40.023 (3)0.033 (3)0.026 (3)0.002 (2)0.002 (2)0.014 (3)
C50.032 (3)0.032 (3)0.028 (3)0.006 (3)0.005 (3)0.012 (3)
C60.037 (4)0.023 (3)0.022 (3)0.003 (3)0.003 (3)0.007 (3)
C70.034 (4)0.028 (3)0.023 (3)0.003 (3)0.000 (3)0.007 (3)
C80.027 (3)0.027 (3)0.018 (3)0.001 (2)0.001 (2)0.004 (2)
C90.027 (3)0.032 (3)0.021 (3)0.000 (3)0.001 (2)0.004 (3)
C100.025 (3)0.036 (4)0.031 (4)0.006 (3)0.006 (3)0.010 (3)
C110.037 (4)0.021 (3)0.016 (3)0.001 (2)0.005 (3)0.005 (2)
C120.031 (3)0.021 (3)0.029 (3)0.001 (2)0.003 (3)0.008 (3)
C130.029 (3)0.024 (3)0.019 (3)0.001 (2)0.005 (2)0.010 (2)
C140.026 (3)0.031 (3)0.031 (4)0.002 (3)0.004 (3)0.009 (3)
C150.032 (4)0.037 (4)0.046 (4)0.005 (3)0.004 (3)0.018 (3)
C160.046 (4)0.028 (3)0.032 (4)0.012 (3)0.007 (3)0.008 (3)
C170.052 (4)0.021 (3)0.030 (4)0.001 (3)0.008 (3)0.008 (3)
C180.027 (3)0.029 (3)0.040 (4)0.004 (3)0.002 (3)0.014 (3)
C190.045 (4)0.029 (3)0.034 (4)0.004 (3)0.004 (3)0.017 (3)
C200.027 (3)0.016 (3)0.022 (3)0.005 (2)0.000 (2)0.004 (2)
C210.025 (3)0.019 (3)0.030 (3)0.002 (2)0.004 (3)0.007 (3)
C220.031 (3)0.019 (3)0.020 (3)0.003 (2)0.001 (2)0.005 (2)
C230.032 (3)0.026 (3)0.036 (4)0.002 (3)0.004 (3)0.016 (3)
C240.037 (4)0.026 (3)0.032 (4)0.003 (3)0.000 (3)0.012 (3)
C250.040 (4)0.022 (3)0.024 (3)0.005 (3)0.001 (3)0.010 (3)
C260.034 (4)0.029 (3)0.027 (3)0.004 (3)0.007 (3)0.007 (3)
C270.031 (3)0.023 (3)0.024 (3)0.005 (2)0.002 (3)0.006 (3)
C280.025 (3)0.033 (3)0.041 (4)0.002 (3)0.005 (3)0.011 (3)
C290.022 (3)0.030 (3)0.040 (4)0.003 (3)0.000 (3)0.010 (3)
C300.030 (3)0.028 (3)0.032 (4)0.004 (3)0.004 (3)0.013 (3)
C310.035 (3)0.022 (3)0.024 (3)0.001 (2)0.002 (3)0.012 (3)
C320.025 (3)0.023 (3)0.033 (3)0.002 (2)0.010 (3)0.017 (3)
C330.037 (4)0.036 (4)0.032 (4)0.002 (3)0.000 (3)0.014 (3)
C340.034 (4)0.048 (4)0.035 (4)0.013 (3)0.007 (3)0.023 (3)
C350.054 (4)0.028 (3)0.035 (4)0.011 (3)0.015 (3)0.017 (3)
C360.048 (4)0.027 (3)0.036 (4)0.005 (3)0.009 (3)0.010 (3)
C370.032 (3)0.030 (3)0.033 (4)0.005 (3)0.005 (3)0.015 (3)
C380.048 (4)0.022 (3)0.034 (4)0.001 (3)0.002 (3)0.017 (3)
Geometric parameters (Å, º) top
Br1—C61.904 (6)C17—H170.9500
Br2—C251.903 (6)C18—H180.9500
S1—C11.743 (6)C19—H19A0.9800
S1—C131.786 (6)C19—H19B0.9800
S2—C201.758 (6)C19—H19C0.9800
S2—C321.782 (6)C20—C311.353 (8)
O1—C111.373 (7)C20—C211.439 (8)
O1—C121.374 (7)C21—C301.391 (9)
O2—C311.376 (8)C21—C221.416 (8)
O2—C301.378 (7)C22—C231.412 (9)
C1—C121.362 (8)C22—C271.434 (8)
C1—C21.447 (8)C23—C241.368 (9)
C2—C111.389 (8)C23—H230.9500
C2—C31.422 (8)C24—C251.409 (9)
C3—C41.420 (8)C24—H240.9500
C3—C81.421 (8)C25—C261.371 (9)
C4—C51.367 (9)C26—C271.411 (9)
C4—H40.9500C26—H260.9500
C5—C61.397 (9)C27—C281.423 (9)
C5—H50.9500C28—C291.37 (1)
C6—C71.356 (9)C28—H280.9500
C7—C81.428 (9)C29—C301.395 (9)
C7—H70.9500C29—H290.9500
C8—C91.431 (9)C31—C381.489 (8)
C9—C101.376 (9)C32—C331.385 (9)
C9—H90.9500C32—C371.385 (9)
C10—C111.385 (9)C33—C341.385 (9)
C10—H100.9500C33—H330.9500
C12—C191.475 (9)C34—C351.37 (1)
C13—C181.375 (8)C34—H340.9500
C13—C141.389 (9)C35—C361.39 (1)
C14—C151.371 (9)C35—H350.9500
C14—H140.9500C36—C371.387 (9)
C15—C161.38 (1)C36—H360.9500
C15—H150.9500C37—H370.9500
C16—C171.37 (1)C38—H38A0.9800
C16—H160.9500C38—H38B0.9800
C17—C181.401 (9)C38—H38C0.9800
C1—S1—C13105.9 (3)H19A—C19—H19C109.5
C20—S2—C32103.8 (3)H19B—C19—H19C109.5
C11—O1—C12106.9 (4)C31—C20—C21107.7 (5)
C31—O2—C30106.2 (4)C31—C20—S2121.9 (5)
C12—C1—C2107.1 (5)C21—C20—S2129.7 (5)
C12—C1—S1122.1 (5)C30—C21—C22118.7 (5)
C2—C1—S1130.3 (4)C30—C21—C20104.6 (5)
C11—C2—C3118.2 (5)C22—C21—C20136.7 (6)
C11—C2—C1105.0 (5)C23—C22—C21124.5 (6)
C3—C2—C1136.8 (5)C23—C22—C27118.4 (5)
C4—C3—C8118.7 (6)C21—C22—C27117.0 (5)
C4—C3—C2123.7 (6)C24—C23—C22121.9 (6)
C8—C3—C2117.6 (5)C24—C23—H23119.0
C5—C4—C3121.1 (6)C22—C23—H23119.0
C5—C4—H4119.4C23—C24—C25118.8 (6)
C3—C4—H4119.4C23—C24—H24120.6
C4—C5—C6119.4 (6)C25—C24—H24120.6
C4—C5—H5120.3C26—C25—C24121.7 (6)
C6—C5—H5120.3C26—C25—Br2119.6 (5)
C7—C6—C5122.2 (6)C24—C25—Br2118.7 (5)
C7—C6—Br1119.3 (5)C25—C26—C27120.1 (6)
C5—C6—Br1118.5 (5)C25—C26—H26119.9
C6—C7—C8119.8 (6)C27—C26—H26119.9
C6—C7—H7120.1C26—C27—C28120.1 (6)
C8—C7—H7120.1C26—C27—C22119.0 (6)
C3—C8—C7118.8 (6)C28—C27—C22120.9 (6)
C3—C8—C9120.8 (6)C29—C28—C27121.5 (6)
C7—C8—C9120.4 (6)C29—C28—H28119.3
C10—C9—C8121.1 (6)C27—C28—H28119.3
C10—C9—H9119.4C28—C29—C30116.7 (6)
C8—C9—H9119.4C28—C29—H29121.7
C9—C10—C11116.7 (6)C30—C29—H29121.7
C9—C10—H10121.6O2—C30—C21110.8 (5)
C11—C10—H10121.6O2—C30—C29124.1 (6)
O1—C11—C10123.9 (5)C21—C30—C29125.1 (6)
O1—C11—C2110.5 (5)C20—C31—O2110.7 (5)
C10—C11—C2125.5 (6)C20—C31—C38133.3 (6)
C1—C12—O1110.4 (5)O2—C31—C38116.0 (5)
C1—C12—C19133.8 (6)C33—C32—C37119.8 (6)
O1—C12—C19115.7 (5)C33—C32—S2116.4 (5)
C18—C13—C14120.8 (6)C37—C32—S2123.7 (5)
C18—C13—S1123.9 (5)C34—C33—C32120.1 (6)
C14—C13—S1115.4 (4)C34—C33—H33120.0
C15—C14—C13119.4 (6)C32—C33—H33120.0
C15—C14—H14120.3C35—C34—C33120.7 (6)
C13—C14—H14120.3C35—C34—H34119.7
C14—C15—C16121.1 (6)C33—C34—H34119.7
C14—C15—H15119.4C34—C35—C36119.3 (6)
C16—C15—H15119.4C34—C35—H35120.3
C17—C16—C15119.0 (6)C36—C35—H35120.3
C17—C16—H16120.5C37—C36—C35120.8 (6)
C15—C16—H16120.5C37—C36—H36119.6
C16—C17—C18121.4 (6)C35—C36—H36119.6
C16—C17—H17119.3C32—C37—C36119.3 (6)
C18—C17—H17119.3C32—C37—H37120.4
C13—C18—C17118.3 (6)C36—C37—H37120.4
C13—C18—H18120.8C31—C38—H38A109.5
C17—C18—H18120.8C31—C38—H38B109.5
C12—C19—H19A109.5H38A—C38—H38B109.5
C12—C19—H19B109.5C31—C38—H38C109.5
H19A—C19—H19B109.5H38A—C38—H38C109.5
C12—C19—H19C109.5H38B—C38—H38C109.5
C13—S1—C1—C12109.2 (5)C32—S2—C20—C31111.8 (5)
C13—S1—C1—C280.1 (6)C32—S2—C20—C2179.3 (6)
C12—C1—C2—C112.4 (6)C31—C20—C21—C300.2 (7)
S1—C1—C2—C11169.4 (5)S2—C20—C21—C30170.3 (5)
C12—C1—C2—C3179.0 (7)C31—C20—C21—C22179.5 (7)
S1—C1—C2—C39.2 (11)S2—C20—C21—C2210.4 (11)
C11—C2—C3—C4177.5 (6)C30—C21—C22—C23179.1 (6)
C1—C2—C3—C44.0 (11)C20—C21—C22—C230.1 (11)
C11—C2—C3—C80.8 (8)C30—C21—C22—C273.2 (8)
C1—C2—C3—C8177.7 (6)C20—C21—C22—C27177.6 (6)
C8—C3—C4—C50.6 (9)C21—C22—C23—C24177.7 (6)
C2—C3—C4—C5178.9 (6)C27—C22—C23—C240.1 (9)
C3—C4—C5—C60.5 (9)C22—C23—C24—C250.8 (9)
C4—C5—C6—C71.4 (10)C23—C24—C25—C260.9 (9)
C4—C5—C6—Br1179.7 (5)C23—C24—C25—Br2179.2 (5)
C5—C6—C7—C81.0 (9)C24—C25—C26—C270.1 (9)
Br1—C6—C7—C8179.9 (4)Br2—C25—C26—C27180.0 (5)
C4—C3—C8—C71.0 (8)C25—C26—C27—C28179.7 (6)
C2—C3—C8—C7179.3 (5)C25—C26—C27—C220.8 (9)
C4—C3—C8—C9179.2 (6)C23—C22—C27—C260.9 (8)
C2—C3—C8—C90.8 (8)C21—C22—C27—C26177.0 (5)
C6—C7—C8—C30.1 (9)C23—C22—C27—C28179.8 (6)
C6—C7—C8—C9180.0 (6)C21—C22—C27—C281.9 (8)
C3—C8—C9—C101.0 (9)C26—C27—C28—C29179.1 (6)
C7—C8—C9—C10179.1 (6)C22—C27—C28—C290.2 (9)
C8—C9—C10—C110.4 (9)C27—C28—C29—C300.9 (10)
C12—O1—C11—C10178.2 (6)C31—O2—C30—C210.1 (7)
C12—O1—C11—C20.3 (6)C31—O2—C30—C29177.8 (6)
C9—C10—C11—O1179.7 (5)C22—C21—C30—O2179.6 (5)
C9—C10—C11—C22.2 (9)C20—C21—C30—O20.2 (7)
C3—C2—C11—O1179.8 (5)C22—C21—C30—C292.7 (9)
C1—C2—C11—O11.3 (6)C20—C21—C30—C29177.9 (6)
C3—C2—C11—C102.4 (9)C28—C29—C30—O2178.0 (6)
C1—C2—C11—C10176.5 (6)C28—C29—C30—C210.6 (10)
C2—C1—C12—O12.7 (6)C21—C20—C31—O20.2 (7)
S1—C1—C12—O1169.9 (4)S2—C20—C31—O2171.2 (4)
C2—C1—C12—C19179.5 (7)C21—C20—C31—C38177.8 (6)
S1—C1—C12—C197.9 (10)S2—C20—C31—C386.7 (10)
C11—O1—C12—C11.9 (6)C30—O2—C31—C200.1 (6)
C11—O1—C12—C19179.8 (5)C30—O2—C31—C38178.3 (5)
C1—S1—C13—C185.5 (6)C20—S2—C32—C33168.5 (5)
C1—S1—C13—C14173.8 (5)C20—S2—C32—C3712.8 (6)
C18—C13—C14—C150.7 (10)C37—C32—C33—C340.6 (10)
S1—C13—C14—C15178.7 (5)S2—C32—C33—C34178.1 (5)
C13—C14—C15—C160.1 (10)C32—C33—C34—C350.0 (10)
C14—C15—C16—C170.0 (11)C33—C34—C35—C360.0 (10)
C15—C16—C17—C180.8 (10)C34—C35—C36—C370.6 (10)
C14—C13—C18—C171.4 (9)C33—C32—C37—C361.2 (9)
S1—C13—C18—C17177.9 (5)S2—C32—C37—C36177.4 (5)
C16—C17—C18—C131.5 (10)C35—C36—C37—C321.3 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C19—H19C···Cg30.982.773.551 (6)137
C38—H38A···Cg50.982.603.498 (6)153

Experimental details

Crystal data
Chemical formulaC19H13BrOS
Mr369.26
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)10.947 (2), 11.130 (2), 13.636 (2)
α, β, γ (°)112.798 (2), 91.999 (3), 90.908 (2)
V3)1529.9 (5)
Z4
Radiation typeMo Kα
µ (mm1)2.82
Crystal size (mm)0.35 × 0.25 × 0.10
Data collection
DiffractometerBruker SMART CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1999)
Tmin, Tmax0.442, 0.760
No. of measured, independent and
observed [I > 2σ(I)] reflections
7613, 5209, 4269
Rint0.025
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.152, 1.14
No. of reflections5209
No. of parameters398
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.62, 0.65

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C19—H19C···Cg30.982.773.551 (6)136.5
C38—H38A···Cg50.982.603.498 (6)152.5
 

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