Literature DB >> 23125809

7-Bromo-1-(3-fluoro-phenyl-sulfon-yl)-2-methyl-naphtho-[2,1-b]furan.

Hong Dae Choi1, Pil Ja Seo, Uk Lee.   

Abstract

In the title compound, C(19)H(12)BrFO(3)S, the 3-fluoro-phenyl ring makes a dihedral angle of 80.85 (5)° with the mean plane [r.m.s. deviation = 0.009 (2)Å] of the naphtho-furan fragment. In the crystal, mol-ecules are linked by slipped π-π inter-actions between the furan and the outer benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.756 (3) Å and slippage of 1.189 (3) Å].

Entities:  

Year:  2012        PMID： 23125809      PMCID： PMC3470396          DOI： 10.1107/S1600536812040470

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2008 ▶, 2011 ▶).

Experimental

Crystal data

C19H12BrFO3S M = 419.26 Triclinic, a = 7.7141 (2) Å b = 8.1619 (2) Å c = 13.4046 (4) Å α = 74.277 (2)° β = 86.410 (2)° γ = 89.044 (2)° V = 810.80 (4) Å3 Z = 2 Mo Kα radiation μ = 2.69 mm−1 T = 173 K 0.28 × 0.24 × 0.23 mm

Data collection

Bruker SMART APEX II CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.573, T max = 0.746 15010 measured reflections 4031 independent reflections 3483 reflections with I > 2σ(I) R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.030 wR(F 2) = 0.075 S = 1.06 4031 reflections 227 parameters H-atom parameters constrained Δρmax = 0.49 e Å−3 Δρmin = −0.40 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, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536812040470/rk2381sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040470/rk2381Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812040470/rk2381Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C19H12BrFO3SZ = 2
Mr = 419.26F(000) = 420
Triclinic, P1Dx = 1.717 Mg m−3
Hall symbol: -P 1Melting point = 472–473 K
a = 7.7141 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.1619 (2) ÅCell parameters from 7012 reflections
c = 13.4046 (4) Åθ = 2.6–28.3°
α = 74.277 (2)°µ = 2.69 mm−1
β = 86.410 (2)°T = 173 K
γ = 89.044 (2)°Block, colourless
V = 810.80 (4) Å30.28 × 0.24 × 0.23 mm
Bruker SMART APEX II CCD diffractometer4031 independent reflections
Radiation source: rotating anode3483 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.047
Detector resolution: 10.0 pixels mm-1θmax = 28.3°, θmin = 1.6°
φ– and ω–scansh = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)k = −10→10
Tmin = 0.573, Tmax = 0.746l = −17→16
15010 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0258P)2 + 0.4345P] where P = (Fo2 + 2Fc2)/3
4031 reflections(Δ/σ)max = 0.001
227 parametersΔρmax = 0.49 e Å−3
0 restraintsΔρmin = −0.40 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.
xyzUiso*/Ueq
Br10.57980 (3)0.18645 (3)0.314671 (17)0.03502 (8)
S10.84031 (6)0.35008 (6)0.82867 (4)0.02420 (11)
F10.3382 (2)−0.0623 (2)0.89171 (12)0.0539 (4)
O10.90963 (19)0.80950 (18)0.64831 (11)0.0290 (3)
O20.92123 (19)0.21364 (19)0.79427 (12)0.0314 (3)
O30.90169 (19)0.3885 (2)0.91876 (11)0.0325 (3)
C10.8517 (2)0.5360 (2)0.72789 (15)0.0234 (4)
C20.8204 (2)0.5642 (2)0.61823 (15)0.0225 (4)
C30.7631 (2)0.4684 (2)0.55178 (15)0.0215 (4)
C40.7185 (3)0.2941 (2)0.58317 (15)0.0261 (4)
H40.72720.23230.65380.031*
C50.6630 (3)0.2119 (3)0.51466 (16)0.0275 (4)
H50.63250.09480.53760.033*
C60.6516 (2)0.3023 (3)0.41023 (16)0.0253 (4)
C70.6938 (3)0.4703 (3)0.37573 (16)0.0270 (4)
H70.68520.52860.30450.032*
C80.7502 (2)0.5582 (2)0.44463 (15)0.0234 (4)
C90.7940 (3)0.7335 (3)0.40720 (16)0.0274 (4)
H90.78450.78930.33570.033*
C100.8488 (3)0.8229 (3)0.47063 (16)0.0276 (4)
H100.87900.93990.44560.033*
C110.8588 (2)0.7340 (2)0.57511 (16)0.0247 (4)
C120.9047 (3)0.6874 (3)0.74099 (16)0.0277 (4)
C130.9565 (3)0.7507 (3)0.82888 (19)0.0394 (5)
H13A1.07690.71760.84360.059*
H13B0.88010.70120.89060.059*
H13C0.94670.87510.81040.059*
C140.6173 (2)0.2986 (3)0.85656 (14)0.0238 (4)
C150.5063 (3)0.4128 (3)0.88799 (16)0.0289 (4)
H150.54630.52230.88790.035*
C160.3356 (3)0.3642 (3)0.91954 (17)0.0354 (5)
H160.25750.44160.94040.043*
C170.2788 (3)0.2043 (3)0.92085 (17)0.0363 (5)
H170.16230.17040.94310.044*
C180.3928 (3)0.0953 (3)0.88949 (17)0.0349 (5)
C190.5630 (3)0.1383 (3)0.85604 (16)0.0298 (4)
H190.63940.06120.83360.036*
U11U22U33U12U13U23
Br10.04802 (14)0.03053 (13)0.02960 (12)−0.00014 (9)−0.00906 (9)−0.01191 (9)
S10.0227 (2)0.0285 (3)0.0205 (2)0.00142 (18)−0.00143 (18)−0.00511 (19)
F10.0640 (10)0.0522 (9)0.0498 (9)−0.0291 (8)0.0038 (8)−0.0209 (7)
O10.0344 (8)0.0268 (7)0.0263 (7)−0.0069 (6)0.0010 (6)−0.0084 (6)
O20.0297 (7)0.0319 (8)0.0309 (8)0.0074 (6)−0.0006 (6)−0.0064 (6)
O30.0311 (7)0.0439 (9)0.0238 (7)−0.0008 (7)−0.0066 (6)−0.0101 (7)
C10.0226 (9)0.0264 (10)0.0206 (9)−0.0019 (7)0.0018 (7)−0.0061 (8)
C20.0218 (9)0.0231 (9)0.0219 (9)0.0006 (7)0.0024 (7)−0.0055 (7)
C30.0180 (8)0.0241 (9)0.0217 (9)0.0011 (7)0.0024 (7)−0.0056 (7)
C40.0311 (10)0.0240 (10)0.0215 (9)0.0004 (8)0.0007 (8)−0.0039 (8)
C50.0335 (10)0.0218 (10)0.0264 (10)−0.0009 (8)−0.0005 (8)−0.0052 (8)
C60.0244 (9)0.0295 (10)0.0245 (10)0.0013 (8)−0.0028 (8)−0.0114 (8)
C70.0288 (10)0.0285 (10)0.0223 (10)0.0029 (8)−0.0028 (8)−0.0044 (8)
C80.0220 (9)0.0249 (10)0.0219 (9)0.0014 (7)0.0005 (7)−0.0047 (8)
C90.0302 (10)0.0261 (10)0.0224 (10)0.0008 (8)−0.0013 (8)−0.0007 (8)
C100.0286 (10)0.0228 (10)0.0288 (10)−0.0038 (8)0.0022 (8)−0.0030 (8)
C110.0233 (9)0.0248 (10)0.0263 (10)−0.0028 (7)0.0017 (8)−0.0081 (8)
C120.0275 (10)0.0310 (11)0.0249 (10)−0.0034 (8)0.0034 (8)−0.0090 (8)
C130.0503 (14)0.0389 (13)0.0328 (12)−0.0120 (11)−0.0007 (10)−0.0160 (10)
C140.0245 (9)0.0287 (10)0.0161 (9)−0.0011 (8)−0.0013 (7)−0.0021 (7)
C150.0287 (10)0.0309 (11)0.0250 (10)0.0022 (8)−0.0013 (8)−0.0041 (8)
C160.0276 (10)0.0470 (14)0.0281 (11)0.0073 (10)0.0001 (9)−0.0050 (10)
C170.0250 (10)0.0559 (15)0.0252 (11)−0.0068 (10)−0.0041 (8)−0.0053 (10)
C180.0413 (12)0.0402 (12)0.0224 (10)−0.0150 (10)−0.0042 (9)−0.0056 (9)
C190.0363 (11)0.0321 (11)0.0209 (10)−0.0009 (9)−0.0005 (8)−0.0075 (8)
Br1—C61.8986 (19)C7—H70.9500
S1—O21.4358 (15)C8—C91.421 (3)
S1—O31.4363 (15)C9—C101.351 (3)
S1—C11.736 (2)C9—H90.9500
S1—C141.770 (2)C10—C111.398 (3)
F1—C181.352 (3)C10—H100.9500
O1—C121.365 (3)C12—C131.487 (3)
O1—C111.371 (2)C13—H13A0.9800
C1—C121.367 (3)C13—H13B0.9800
C1—C21.460 (3)C13—H13C0.9800
C2—C111.378 (3)C14—C191.382 (3)
C2—C31.428 (3)C14—C151.386 (3)
C3—C41.412 (3)C15—C161.388 (3)
C3—C81.434 (3)C15—H150.9500
C4—C51.367 (3)C16—C171.379 (3)
C4—H40.9500C16—H160.9500
C5—C61.402 (3)C17—C181.369 (3)
C5—H50.9500C17—H170.9500
C6—C71.361 (3)C18—C191.380 (3)
C7—C81.406 (3)C19—H190.9500
O2—S1—O3118.58 (9)C9—C10—C11116.43 (19)
O2—S1—C1109.57 (9)C9—C10—H10121.8
O3—S1—C1107.58 (9)C11—C10—H10121.8
O2—S1—C14107.07 (9)O1—C11—C2111.44 (17)
O3—S1—C14106.73 (9)O1—C11—C10122.61 (18)
C1—S1—C14106.70 (9)C2—C11—C10125.94 (19)
C12—O1—C11107.20 (15)O1—C12—C1109.96 (17)
C12—C1—C2107.40 (17)O1—C12—C13113.53 (18)
C12—C1—S1122.42 (15)C1—C12—C13136.5 (2)
C2—C1—S1130.10 (15)C12—C13—H13A109.5
C11—C2—C3118.08 (18)C12—C13—H13B109.5
C11—C2—C1104.00 (17)H13A—C13—H13B109.5
C3—C2—C1137.92 (18)C12—C13—H13C109.5
C4—C3—C2125.37 (18)H13A—C13—H13C109.5
C4—C3—C8117.97 (18)H13B—C13—H13C109.5
C2—C3—C8116.66 (17)C19—C14—C15121.94 (19)
C5—C4—C3121.73 (18)C19—C14—S1118.52 (15)
C5—C4—H4119.1C15—C14—S1119.23 (16)
C3—C4—H4119.1C14—C15—C16118.7 (2)
C4—C5—C6119.28 (19)C14—C15—H15120.6
C4—C5—H5120.4C16—C15—H15120.6
C6—C5—H5120.4C17—C16—C15120.5 (2)
C7—C6—C5121.39 (18)C17—C16—H16119.8
C7—C6—Br1119.44 (15)C15—C16—H16119.8
C5—C6—Br1119.15 (15)C18—C17—C16118.9 (2)
C6—C7—C8120.53 (18)C18—C17—H17120.5
C6—C7—H7119.7C16—C17—H17120.5
C8—C7—H7119.7F1—C18—C17119.1 (2)
C7—C8—C9119.75 (18)F1—C18—C19118.0 (2)
C7—C8—C3119.09 (18)C17—C18—C19122.9 (2)
C9—C8—C3121.16 (18)C18—C19—C14117.1 (2)
C10—C9—C8121.72 (19)C18—C19—H19121.5
C10—C9—H9119.1C14—C19—H19121.5
C8—C9—H9119.1
O2—S1—C1—C12−132.60 (17)C12—O1—C11—C20.1 (2)
O3—S1—C1—C12−2.4 (2)C12—O1—C11—C10179.98 (18)
C14—S1—C1—C12111.81 (17)C3—C2—C11—O1179.17 (16)
O2—S1—C1—C243.6 (2)C1—C2—C11—O1−0.1 (2)
O3—S1—C1—C2173.78 (17)C3—C2—C11—C10−0.7 (3)
C14—S1—C1—C2−72.00 (19)C1—C2—C11—C10−179.99 (19)
C12—C1—C2—C110.1 (2)C9—C10—C11—O1−178.91 (18)
S1—C1—C2—C11−176.57 (15)C9—C10—C11—C21.0 (3)
C12—C1—C2—C3−178.9 (2)C11—O1—C12—C10.0 (2)
S1—C1—C2—C34.4 (3)C11—O1—C12—C13−179.86 (17)
C11—C2—C3—C4−179.95 (18)C2—C1—C12—O10.0 (2)
C1—C2—C3—C4−1.0 (4)S1—C1—C12—O1176.92 (13)
C11—C2—C3—C80.0 (3)C2—C1—C12—C13179.8 (2)
C1—C2—C3—C8178.9 (2)S1—C1—C12—C13−3.3 (4)
C2—C3—C4—C5179.37 (18)O2—S1—C14—C198.63 (18)
C8—C3—C4—C5−0.5 (3)O3—S1—C14—C19−119.31 (16)
C3—C4—C5—C60.6 (3)C1—S1—C14—C19125.89 (16)
C4—C5—C6—C7−0.3 (3)O2—S1—C14—C15−177.62 (15)
C4—C5—C6—Br1178.52 (15)O3—S1—C14—C1554.44 (18)
C5—C6—C7—C8−0.1 (3)C1—S1—C14—C15−60.36 (18)
Br1—C6—C7—C8−178.92 (14)C19—C14—C15—C16−0.1 (3)
C6—C7—C8—C9179.91 (18)S1—C14—C15—C16−173.67 (16)
C6—C7—C8—C30.2 (3)C14—C15—C16—C170.9 (3)
C4—C3—C8—C70.1 (3)C15—C16—C17—C18−0.7 (3)
C2—C3—C8—C7−179.79 (17)C16—C17—C18—F1179.29 (19)
C4—C3—C8—C9−179.58 (17)C16—C17—C18—C19−0.3 (3)
C2—C3—C8—C90.5 (3)F1—C18—C19—C14−178.59 (18)
C7—C8—C9—C10−179.96 (19)C17—C18—C19—C141.0 (3)
C3—C8—C9—C10−0.2 (3)C15—C14—C19—C18−0.7 (3)
C8—C9—C10—C11−0.5 (3)S1—C14—C19—C18172.82 (15)
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1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  7-Bromo-2-methyl-1-tosyl-naphtho[2,1-b]furan.

Authors:  Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-05-24

3.  7-Bromo-1-(4-fluoro-phenyl-sulfon-yl)-2-methyl-naphtho-[2,1-b]furan.

Authors:  Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-01-08
  3 in total

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