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COMMUNICATIONS
ISSN: 2056-9890

1-(4-Bromo­phenyl­sulfon­yl)-2-methyl­naphtho­[2,1-b]furan

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

(Received 25 June 2012; accepted 28 June 2012; online 4 July 2012)

In the title compound, C19H13BrO3S, the 4-bromo­phenyl ring makes a dihedral angle of 64.11 (2)° with the mean plane [r.m.s. deviation = 0.01 (2) Å] of the naphtho­furan ring. In the crystal, mol­ecules are linked by weak C—H⋯O and C—H⋯π inter­actions. The crystal structure also exhibits slipped ππ inter­actions between the central naphtho­furan benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.559 (2), slippage = 1.036 (2) Å], and between the central naphtho­furan benzene ring and the furan ring of neighbouring mol­ecules [centroid–centroid distance = 3.655 (2), slippage = 1.136 (2) Å].

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2008[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008). Acta Cryst. E64, o727.], 2012[Choi, H. D., Seo, P. J. & Lee, U. (2012). Acta Cryst. E68, o1193.]).

[Scheme 1]

Experimental

Crystal data
  • C19H13BrO3S

  • Mr = 401.26

  • Triclinic, [P \overline 1]

  • a = 6.9579 (2) Å

  • b = 10.9709 (4) Å

  • c = 11.4207 (4) Å

  • α = 110.510 (2)°

  • β = 105.886 (2)°

  • γ = 91.656 (2)°

  • V = 777.77 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 2.79 mm−1

  • T = 173 K

  • 0.29 × 0.13 × 0.10 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.555, Tmax = 0.746

  • 14423 measured reflections

  • 3876 independent reflections

  • 3201 reflections with I > 2σ(I)

  • Rint = 0.036

Refinement
  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.084

  • S = 1.05

  • 3876 reflections

  • 218 parameters

  • H-atom parameters constrained

  • Δρmax = 0.49 e Å−3

  • Δρmin = −0.35 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

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

D—H⋯A D—H H⋯A DA D—H⋯A
C16—H16⋯O2i 0.95 2.49 3.197 (2) 131
C19—H19⋯O3ii 0.95 2.47 3.177 (2) 132
C9—H9⋯Cg1iii 0.95 2.96 3.782 (2) 120
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y+2, -z+2; (iii) -x-1, -y-1, -z-1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

As a part of our ongoing study of 2-methylnaphtho[2,1-b]furan derivatives containing 1-phenylsulfonyl (Choi et al., 2008) and 1-(4-methylphenylsulfonyl) (Choi et al., 2012) substituents, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the naphthofuran unit is essentially planar, with a mean deviation of 0.017 (2) Å from the least-squares plane defined by the thirteen constituent atoms. The dihedral angle between the 4-bromophenyl ring and the mean plane of the naphthofuran ring is 64.11 (2)°. In the crystal structure (Fig. 2), molecules are connected by weak intermolecular C—H···O and C—H···π interactions (Table 1, Cg1 is the centroid of the C14–C19 4-bromophenyl ring). In the crystal structure (Fig. 3), molecules are connected ππ interactions; the first one between the central naphthofuran benzene rings of neighbouring molecules, with a Cg2···Cg2ii distance of 3.559 (2) Å and an interplanar distance of 3.405 (2) Å resulting in a slippage of 1.036 (2) Å (Cg2 is the centroid of the C2/C3/C8/C9/C10/C11 benzene ring), and the second one between the central naphthofuran benzene ring and the furan ring of neighbouring molecules, with a Cg2···Cg3i distance of 3.655 (2) Å and an interplanar distance of 3.474 (2) Å resulting in a slippage of 1.136 (2) Å (Cg3 is the centroid of the C1/C2/C11/O1/C12 furan ring).

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2008, 2012).

Experimental top

3-Chloroperoxybenzoic acid (77%, 448 mg, 2.0 mmol) was added in small portions to a stirred solution of 1-(4-bromophenylsulfanyl)-2-methylnaphtho [2,1-b]furan (332 mg, 0.9 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 8h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (benzene) to afford the title compound as a colorless solid [yield 71%, m.p. 452–453 K; Rf = 0.69 (benzene)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in acetone 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. Uiso(H) = 1.2Ueq(C) for aryl and 1.5Ueq(C) for methyl H atoms. The positions of methyl hydrogens were optimized rotationally.

Structure description top

As a part of our ongoing study of 2-methylnaphtho[2,1-b]furan derivatives containing 1-phenylsulfonyl (Choi et al., 2008) and 1-(4-methylphenylsulfonyl) (Choi et al., 2012) substituents, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the naphthofuran unit is essentially planar, with a mean deviation of 0.017 (2) Å from the least-squares plane defined by the thirteen constituent atoms. The dihedral angle between the 4-bromophenyl ring and the mean plane of the naphthofuran ring is 64.11 (2)°. In the crystal structure (Fig. 2), molecules are connected by weak intermolecular C—H···O and C—H···π interactions (Table 1, Cg1 is the centroid of the C14–C19 4-bromophenyl ring). In the crystal structure (Fig. 3), molecules are connected ππ interactions; the first one between the central naphthofuran benzene rings of neighbouring molecules, with a Cg2···Cg2ii distance of 3.559 (2) Å and an interplanar distance of 3.405 (2) Å resulting in a slippage of 1.036 (2) Å (Cg2 is the centroid of the C2/C3/C8/C9/C10/C11 benzene ring), and the second one between the central naphthofuran benzene ring and the furan ring of neighbouring molecules, with a Cg2···Cg3i distance of 3.655 (2) Å and an interplanar distance of 3.474 (2) Å resulting in a slippage of 1.136 (2) Å (Cg3 is the centroid of the C1/C2/C11/O1/C12 furan ring).

For background information and the crystal structures of related compounds, see: Choi et al. (2008, 2012).

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 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] 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.
[Figure 2] Fig. 2. A view of the C—H···O and C—H···π interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) - x + 1, - y + 1, - z + 2; (ii) - x + 1, - y + 2, - z + 2; (iii) - x + 1, - y + 1, - z + 1.]
[Figure 3] Fig. 3. A view of the ππ interactions (dotted lines) in the crystal structure of the title compound. All H atoms were omitted for clarity. [Symmetry codes: (i) - x , - y + 1, - z + 1; (ii)- x + 1, - y + 1, - z + 1.]
1-(4-Bromophenylsulfonyl)-2-methylnaphtho[2,1-b]furan top
Crystal data top
C19H13BrO3SZ = 2
Mr = 401.26F(000) = 404
Triclinic, P1Dx = 1.713 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.9579 (2) ÅCell parameters from 6011 reflections
b = 10.9709 (4) Åθ = 2.2–27.9°
c = 11.4207 (4) ŵ = 2.79 mm1
α = 110.510 (2)°T = 173 K
β = 105.886 (2)°Block, colourless
γ = 91.656 (2)°0.29 × 0.13 × 0.10 mm
V = 777.77 (5) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer
3876 independent reflections
Radiation source: rotating anode3201 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.036
Detector resolution: 10.0 pixels mm-1θmax = 28.3°, θmin = 2.0°
φ and ω scansh = 98
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1414
Tmin = 0.555, Tmax = 0.746l = 1515
14423 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)] = 0.032Hydrogen site location: difference Fourier map
wR(F2) = 0.084H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0411P)2 + 0.2709P]
where P = (Fo2 + 2Fc2)/3
3876 reflections(Δ/σ)max = 0.001
218 parametersΔρmax = 0.49 e Å3
0 restraintsΔρmin = 0.35 e Å3
Crystal data top
C19H13BrO3Sγ = 91.656 (2)°
Mr = 401.26V = 777.77 (5) Å3
Triclinic, P1Z = 2
a = 6.9579 (2) ÅMo Kα radiation
b = 10.9709 (4) ŵ = 2.79 mm1
c = 11.4207 (4) ÅT = 173 K
α = 110.510 (2)°0.29 × 0.13 × 0.10 mm
β = 105.886 (2)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
3876 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
3201 reflections with I > 2σ(I)
Tmin = 0.555, Tmax = 0.746Rint = 0.036
14423 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.084H-atom parameters constrained
S = 1.05Δρmax = 0.49 e Å3
3876 reflectionsΔρmin = 0.35 e Å3
218 parameters
Special details top

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
xyzUiso*/Ueq
Br11.25056 (3)0.78521 (2)1.20765 (2)0.04071 (10)
S10.33058 (8)0.71206 (4)0.86111 (5)0.02364 (12)
O10.2860 (2)0.71224 (15)0.51468 (15)0.0292 (3)
O20.2305 (2)0.60540 (13)0.87692 (14)0.0279 (3)
O30.2685 (2)0.83982 (14)0.90608 (16)0.0316 (3)
C10.3103 (3)0.67109 (19)0.6958 (2)0.0239 (4)
C20.2740 (3)0.54502 (19)0.5872 (2)0.0230 (4)
C30.2529 (3)0.40719 (19)0.5655 (2)0.0237 (4)
C40.2678 (3)0.3548 (2)0.6634 (2)0.0290 (4)
H40.29240.41280.75180.035*
C50.2476 (4)0.2215 (2)0.6336 (2)0.0337 (5)
H50.25870.18860.70150.040*
C60.2108 (4)0.1340 (2)0.5044 (2)0.0366 (5)
H60.19700.04190.48440.044*
C70.1949 (3)0.1816 (2)0.4076 (2)0.0342 (5)
H70.16940.12150.31990.041*
C80.2153 (3)0.3179 (2)0.4338 (2)0.0270 (4)
C90.1972 (3)0.3626 (2)0.3291 (2)0.0321 (5)
H90.16900.30010.24220.038*
C100.2193 (3)0.4924 (2)0.3507 (2)0.0310 (5)
H100.20820.52290.28120.037*
C110.2592 (3)0.5787 (2)0.4802 (2)0.0270 (4)
C120.3190 (3)0.7668 (2)0.6459 (2)0.0272 (4)
C130.3533 (4)0.9123 (2)0.6993 (2)0.0350 (5)
H13A0.42140.94300.64810.053*
H13B0.43760.94440.79110.053*
H13C0.22340.94580.69400.053*
C140.5890 (3)0.72911 (18)0.94600 (19)0.0234 (4)
C150.6697 (3)0.62392 (19)0.9740 (2)0.0274 (4)
H150.58880.54080.94050.033*
C160.8677 (3)0.6410 (2)1.0507 (2)0.0284 (4)
H160.92310.57041.07170.034*
C170.9844 (3)0.7619 (2)1.0966 (2)0.0280 (4)
C180.9081 (3)0.8657 (2)1.0663 (2)0.0310 (5)
H180.99150.94741.09650.037*
C190.7094 (3)0.84936 (19)0.9916 (2)0.0280 (4)
H190.65480.92050.97130.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.03136 (14)0.04733 (16)0.03750 (15)0.00121 (10)0.00038 (10)0.01757 (12)
S10.0257 (2)0.0192 (2)0.0267 (3)0.00392 (18)0.0099 (2)0.00780 (19)
O10.0271 (8)0.0331 (8)0.0317 (8)0.0034 (6)0.0083 (7)0.0178 (7)
O20.0308 (8)0.0245 (7)0.0309 (8)0.0017 (6)0.0122 (7)0.0113 (6)
O30.0346 (8)0.0241 (7)0.0386 (9)0.0103 (6)0.0165 (7)0.0102 (6)
C10.0223 (10)0.0236 (9)0.0261 (10)0.0041 (8)0.0067 (8)0.0100 (8)
C20.0161 (9)0.0265 (9)0.0263 (10)0.0037 (7)0.0062 (8)0.0101 (8)
C30.0161 (9)0.0245 (9)0.0269 (10)0.0035 (7)0.0041 (8)0.0072 (8)
C40.0297 (11)0.0254 (10)0.0304 (11)0.0052 (8)0.0068 (9)0.0100 (9)
C50.0369 (12)0.0254 (10)0.0367 (13)0.0050 (9)0.0075 (10)0.0119 (10)
C60.0354 (12)0.0223 (10)0.0458 (14)0.0048 (9)0.0109 (11)0.0064 (10)
C70.0295 (11)0.0288 (11)0.0328 (12)0.0015 (9)0.0077 (10)0.0007 (9)
C80.0176 (9)0.0305 (10)0.0292 (11)0.0035 (8)0.0067 (8)0.0070 (9)
C90.0243 (10)0.0408 (12)0.0245 (11)0.0016 (9)0.0066 (9)0.0050 (9)
C100.0241 (10)0.0431 (12)0.0275 (11)0.0044 (9)0.0077 (9)0.0153 (10)
C110.0190 (9)0.0314 (10)0.0325 (11)0.0056 (8)0.0079 (8)0.0139 (9)
C120.0233 (10)0.0285 (10)0.0319 (11)0.0046 (8)0.0088 (9)0.0134 (9)
C130.0399 (13)0.0276 (11)0.0429 (14)0.0050 (9)0.0135 (11)0.0186 (10)
C140.0263 (10)0.0204 (9)0.0231 (10)0.0033 (7)0.0085 (8)0.0068 (8)
C150.0298 (11)0.0200 (9)0.0318 (11)0.0026 (8)0.0103 (9)0.0084 (8)
C160.0311 (11)0.0257 (10)0.0304 (11)0.0060 (8)0.0101 (9)0.0120 (9)
C170.0263 (10)0.0319 (11)0.0250 (11)0.0020 (8)0.0076 (9)0.0100 (9)
C180.0335 (11)0.0259 (10)0.0287 (11)0.0037 (9)0.0056 (9)0.0079 (9)
C190.0344 (11)0.0207 (9)0.0278 (11)0.0032 (8)0.0080 (9)0.0091 (8)
Geometric parameters (Å, º) top
Br1—C171.888 (2)C7—H70.9500
S1—O21.4340 (14)C8—C91.421 (3)
S1—O31.4376 (15)C9—C101.354 (3)
S1—C11.744 (2)C9—H90.9500
S1—C141.763 (2)C10—C111.393 (3)
O1—C121.353 (3)C10—H100.9500
O1—C111.370 (2)C12—C131.482 (3)
C1—C121.366 (3)C13—H13A0.9800
C1—C21.457 (3)C13—H13B0.9800
C2—C111.375 (3)C13—H13C0.9800
C2—C31.440 (3)C14—C191.389 (3)
C3—C41.407 (3)C14—C151.396 (3)
C3—C81.424 (3)C15—C161.382 (3)
C4—C51.374 (3)C15—H150.9500
C4—H40.9500C16—C171.383 (3)
C5—C61.396 (3)C16—H160.9500
C5—H50.9500C17—C181.381 (3)
C6—C71.360 (3)C18—C191.380 (3)
C6—H60.9500C18—H180.9500
C7—C81.413 (3)C19—H190.9500
O2—S1—O3118.77 (9)C9—C10—C11116.5 (2)
O2—S1—C1109.36 (9)C9—C10—H10121.8
O3—S1—C1107.02 (9)C11—C10—H10121.8
O2—S1—C14107.25 (9)O1—C11—C2111.59 (18)
O3—S1—C14106.85 (9)O1—C11—C10121.95 (19)
C1—S1—C14107.03 (9)C2—C11—C10126.4 (2)
C12—O1—C11107.05 (16)O1—C12—C1110.30 (18)
C12—C1—C2107.19 (18)O1—C12—C13113.74 (18)
C12—C1—S1120.68 (16)C1—C12—C13136.0 (2)
C2—C1—S1132.06 (15)C12—C13—H13A109.5
C11—C2—C3117.54 (19)C12—C13—H13B109.5
C11—C2—C1103.83 (17)H13A—C13—H13B109.5
C3—C2—C1138.62 (19)C12—C13—H13C109.5
C4—C3—C8118.08 (19)H13A—C13—H13C109.5
C4—C3—C2125.39 (19)H13B—C13—H13C109.5
C8—C3—C2116.52 (19)C19—C14—C15120.02 (19)
C5—C4—C3121.3 (2)C19—C14—S1119.99 (16)
C5—C4—H4119.4C15—C14—S1119.88 (15)
C3—C4—H4119.4C16—C15—C14119.82 (18)
C4—C5—C6120.6 (2)C16—C15—H15120.1
C4—C5—H5119.7C14—C15—H15120.1
C6—C5—H5119.7C15—C16—C17119.3 (2)
C7—C6—C5119.4 (2)C15—C16—H16120.4
C7—C6—H6120.3C17—C16—H16120.4
C5—C6—H6120.3C18—C17—C16121.5 (2)
C6—C7—C8121.9 (2)C18—C17—Br1119.98 (16)
C6—C7—H7119.1C16—C17—Br1118.51 (17)
C8—C7—H7119.1C19—C18—C17119.25 (19)
C7—C8—C9119.7 (2)C19—C18—H18120.4
C7—C8—C3118.7 (2)C17—C18—H18120.4
C9—C8—C3121.7 (2)C18—C19—C14120.12 (19)
C10—C9—C8121.3 (2)C18—C19—H19119.9
C10—C9—H9119.3C14—C19—H19119.9
C8—C9—H9119.3
O2—S1—C1—C12154.18 (16)C12—O1—C11—C10179.18 (19)
O3—S1—C1—C1224.32 (19)C3—C2—C11—O1178.77 (16)
C14—S1—C1—C1289.95 (18)C1—C2—C11—O10.9 (2)
O2—S1—C1—C222.4 (2)C3—C2—C11—C102.2 (3)
O3—S1—C1—C2152.26 (19)C1—C2—C11—C10178.2 (2)
C14—S1—C1—C293.5 (2)C9—C10—C11—O1179.53 (18)
C12—C1—C2—C111.5 (2)C9—C10—C11—C21.5 (3)
S1—C1—C2—C11175.45 (16)C11—O1—C12—C11.1 (2)
C12—C1—C2—C3178.0 (2)C11—O1—C12—C13179.40 (17)
S1—C1—C2—C35.0 (4)C2—C1—C12—O11.6 (2)
C11—C2—C3—C4178.58 (19)S1—C1—C12—O1175.75 (14)
C1—C2—C3—C40.9 (4)C2—C1—C12—C13179.0 (2)
C11—C2—C3—C80.9 (3)S1—C1—C12—C133.7 (4)
C1—C2—C3—C8179.6 (2)O2—S1—C14—C19155.16 (16)
C8—C3—C4—C50.2 (3)O3—S1—C14—C1926.80 (19)
C2—C3—C4—C5179.3 (2)C1—S1—C14—C1987.57 (18)
C3—C4—C5—C60.2 (4)O2—S1—C14—C1521.08 (19)
C4—C5—C6—C70.0 (4)O3—S1—C14—C15149.44 (16)
C5—C6—C7—C80.2 (3)C1—S1—C14—C1596.18 (17)
C6—C7—C8—C9179.9 (2)C19—C14—C15—C162.1 (3)
C6—C7—C8—C30.2 (3)S1—C14—C15—C16174.17 (15)
C4—C3—C8—C70.0 (3)C14—C15—C16—C171.2 (3)
C2—C3—C8—C7179.52 (18)C15—C16—C17—C180.7 (3)
C4—C3—C8—C9179.72 (19)C15—C16—C17—Br1177.18 (15)
C2—C3—C8—C90.7 (3)C16—C17—C18—C191.8 (3)
C7—C8—C9—C10178.8 (2)Br1—C17—C18—C19176.05 (16)
C3—C8—C9—C101.4 (3)C17—C18—C19—C141.0 (3)
C8—C9—C10—C110.4 (3)C15—C14—C19—C181.0 (3)
C12—O1—C11—C20.1 (2)S1—C14—C19—C18175.27 (16)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C14–C19 4-bromophenyl ring.
D—H···AD—HH···AD···AD—H···A
C16—H16···O2i0.952.493.197 (2)131
C19—H19···O3ii0.952.473.177 (2)132
C9—H9···Cg1iii0.952.963.782 (2)120
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+1, y+2, z+2; (iii) x1, y1, z1.

Experimental details

Crystal data
Chemical formulaC19H13BrO3S
Mr401.26
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)6.9579 (2), 10.9709 (4), 11.4207 (4)
α, β, γ (°)110.510 (2), 105.886 (2), 91.656 (2)
V3)777.77 (5)
Z2
Radiation typeMo Kα
µ (mm1)2.79
Crystal size (mm)0.29 × 0.13 × 0.10
Data collection
DiffractometerBruker SMART APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.555, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
14423, 3876, 3201
Rint0.036
(sin θ/λ)max1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.084, 1.05
No. of reflections3876
No. of parameters218
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.49, 0.35

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C14–C19 4-bromophenyl ring.
D—H···AD—HH···AD···AD—H···A
C16—H16···O2i0.952.493.197 (2)130.8
C19—H19···O3ii0.952.473.177 (2)131.5
C9—H9···Cg1iii0.952.963.782 (2)119.6
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+1, y+2, z+2; (iii) x1, y1, z1.
 

References

First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationBruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChoi, H. D., Seo, P. J. & Lee, U. (2012). Acta Cryst. E68, o1193.  CSD CrossRef IUCr Journals Google Scholar
First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008). Acta Cryst. E64, o727.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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