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The syntheses of three bis­(benzo[b]thio­phen-2-yl)methane derivatives, namely bis­(benzo[b]thio­phen-2-yl)methanone, C17H10OS2, (I), 1,1-bis­(benzo[b]thio­phen-2-yl)-3-(tri­methyl­sil­yl)prop-2-yn-1-ol, C22H20OS2Si, (II), and 1,1-bis­(benzo[b]thio­phen-2-yl)prop-2-yn-1-ol, C19H12OS2, (III), are described and their crystal structures discussed comparatively. The conformation of ketone (I) and the respective analogues are rather similar for most of the compounds compared. This is true for the inter­planar angles, the Car­yl—Cbridge—Car­yl angles and the dihedral angles. The best resemblance is found for a bioisotere of (I), viz. 2,2′-dinaphthyl ketone, (VII). By way of inter­est, the crystal packings also reveal similarities between (I) and (VII). In (I), the edge-to-face inter­actions seen between two napthyl residues in (VII) are substituted by S...π contacts between the benzo[b]thio­phen-2-yl units in (I). In the structures of the bis­(benzo[b]thio­phen-2-yl)methanols, i.e. (II) and (III), the inter­planar angles are also quite similar compared with analogues and related active pharmaceutical ingredients (APIs) containing the dithiophen-2-yl­methane scaf­fold, though the dihedral angles show a larger variability and produce unsymmetrical mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616012973/eg3204sup1.cif
Contains datablocks I, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616012973/eg3204IIsup3.hkl
Contains datablock II

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616012973/eg3204Isup3.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616012973/eg3204IIsup4.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616012973/eg3204IIIsup5.cml
Supplementary material

CCDC references: 1498665; 1498664; 1498663

Computing details top

For all compounds, data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-NT (Bruker, 2008); data reduction: SAINT-NT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(I) Bis(benzo[b]thiophen-2-yl)methanone top
Crystal data top
C17H10OS2Dx = 1.478 Mg m3
Mr = 294.37Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Aba2Cell parameters from 9041 reflections
a = 18.2186 (4) Åθ = 2.3–35.0°
b = 20.0166 (4) ŵ = 0.39 mm1
c = 7.2534 (2) ÅT = 100 K
V = 2645.13 (11) Å3Plate, colourless
Z = 80.35 × 0.34 × 0.10 mm
F(000) = 1216
Data collection top
Bruker Kappa goniometer with an APEXII CCD area detector
diffractometer
2282 reflections with I > 2σ(I)
phi and ω scansRint = 0.027
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
θmax = 25.0°, θmin = 2.0°
Tmin = 0.875, Tmax = 0.962h = 1821
13345 measured reflectionsk = 2323
2327 independent reflectionsl = 88
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.025 w = 1/[σ2(Fo2) + (0.0377P)2 + 3.9183P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.067(Δ/σ)max = 0.001
S = 0.99Δρmax = 0.42 e Å3
2327 reflectionsΔρmin = 0.28 e Å3
181 parametersAbsolute structure: Flack x determined using 1027 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004)
1 restraintAbsolute structure parameter: 0.03 (2)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.75309 (12)0.69981 (10)1.0553 (3)0.0223 (5)
S10.76808 (4)0.55431 (4)1.10846 (11)0.01741 (19)
S20.84820 (4)0.80488 (3)0.88387 (12)0.01572 (18)
C10.82947 (16)0.60759 (14)0.9991 (4)0.0131 (6)
C20.88343 (17)0.57534 (13)0.8931 (4)0.0153 (6)
H20.92140.59700.82590.018*
C30.87191 (15)0.50314 (15)0.9026 (4)0.0141 (6)
C40.91093 (16)0.45231 (15)0.8115 (4)0.0168 (6)
H40.95110.46320.73350.020*
C50.89051 (16)0.38673 (15)0.8364 (4)0.0173 (7)
H50.91710.35230.77590.021*
C60.83086 (17)0.37018 (15)0.9502 (4)0.0170 (6)
H60.81750.32460.96530.020*
C70.79150 (16)0.41898 (15)1.0403 (4)0.0161 (6)
H70.75120.40771.11720.019*
C80.81227 (15)0.48537 (14)1.0158 (4)0.0138 (6)
C90.87383 (16)0.72714 (13)0.9694 (4)0.0129 (6)
C100.94780 (16)0.72143 (14)1.0019 (4)0.0139 (6)
H100.97080.68211.04720.017*
C110.98609 (16)0.78209 (14)0.9592 (4)0.0134 (6)
C121.06093 (17)0.79737 (14)0.9823 (4)0.0152 (6)
H121.09370.76511.03160.018*
C131.08617 (17)0.85968 (15)0.9327 (4)0.0170 (7)
H131.13660.87030.94930.020*
C141.03856 (18)0.90768 (15)0.8579 (4)0.0186 (7)
H141.05740.95000.82240.022*
C150.96454 (17)0.89438 (15)0.8351 (4)0.0161 (6)
H150.93240.92690.78440.019*
C160.93852 (15)0.83169 (14)0.8887 (4)0.0136 (6)
C170.81376 (16)0.67971 (15)1.0119 (4)0.0145 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0143 (10)0.0178 (10)0.0348 (14)0.0010 (9)0.0053 (10)0.0023 (10)
S10.0166 (3)0.0166 (3)0.0191 (4)0.0012 (3)0.0029 (3)0.0007 (3)
S20.0132 (3)0.0129 (3)0.0210 (4)0.0014 (3)0.0003 (3)0.0016 (3)
C10.0111 (13)0.0164 (14)0.0117 (15)0.0034 (11)0.0003 (11)0.0015 (12)
C20.0275 (16)0.0070 (13)0.0114 (14)0.0034 (11)0.0136 (14)0.0020 (12)
C30.0131 (13)0.0169 (14)0.0121 (15)0.0016 (11)0.0040 (13)0.0013 (12)
C40.0128 (14)0.0233 (15)0.0143 (15)0.0018 (12)0.0010 (13)0.0016 (12)
C50.0155 (15)0.0194 (15)0.0169 (16)0.0041 (12)0.0041 (12)0.0046 (12)
C60.0199 (15)0.0129 (14)0.0182 (15)0.0017 (12)0.0076 (13)0.0008 (11)
C70.0128 (14)0.0202 (15)0.0152 (15)0.0023 (12)0.0022 (12)0.0046 (12)
C80.0119 (14)0.0178 (14)0.0117 (14)0.0001 (11)0.0022 (11)0.0015 (12)
C90.0151 (14)0.0105 (13)0.0131 (14)0.0012 (11)0.0014 (11)0.0020 (11)
C100.0188 (14)0.0124 (13)0.0107 (15)0.0033 (12)0.0000 (12)0.0002 (11)
C110.0167 (14)0.0136 (13)0.0101 (13)0.0013 (11)0.0007 (11)0.0014 (11)
C120.0159 (15)0.0173 (14)0.0123 (15)0.0016 (11)0.0004 (12)0.0012 (12)
C130.0147 (14)0.0195 (15)0.0167 (16)0.0046 (12)0.0015 (11)0.0058 (12)
C140.0243 (16)0.0122 (13)0.0193 (16)0.0054 (12)0.0039 (12)0.0018 (12)
C150.0200 (15)0.0115 (14)0.0168 (16)0.0013 (12)0.0014 (12)0.0005 (11)
C160.0132 (13)0.0140 (13)0.0137 (13)0.0016 (11)0.0015 (12)0.0023 (13)
C170.0135 (15)0.0162 (14)0.0138 (15)0.0011 (11)0.0004 (11)0.0011 (12)
Geometric parameters (Å, º) top
O1—C171.217 (4)C7—C81.393 (4)
S1—C81.733 (3)C7—H70.9500
S1—C11.737 (3)C9—C101.373 (4)
S2—C161.731 (3)C9—C171.481 (4)
S2—C91.739 (3)C10—C111.434 (4)
C1—C21.405 (4)C10—H100.9500
C1—C171.475 (4)C11—C121.407 (4)
C2—C31.462 (4)C11—C161.414 (4)
C2—H20.9500C12—C131.377 (4)
C3—C41.406 (4)C12—H120.9500
C3—C81.408 (4)C13—C141.404 (4)
C4—C51.376 (4)C13—H130.9500
C4—H40.9500C14—C151.384 (4)
C5—C61.405 (4)C14—H140.9500
C5—H50.9500C15—C161.397 (4)
C6—C71.376 (4)C15—H150.9500
C6—H60.9500
C8—S1—C190.71 (14)C10—C9—S2113.5 (2)
C16—S2—C990.85 (14)C17—C9—S2116.7 (2)
C2—C1—C17128.3 (3)C9—C10—C11111.7 (3)
C2—C1—S1114.7 (2)C9—C10—H10124.1
C17—C1—S1116.6 (2)C11—C10—H10124.1
C1—C2—C3109.1 (3)C12—C11—C16119.0 (3)
C1—C2—H2125.4C12—C11—C10129.0 (3)
C3—C2—H2125.4C16—C11—C10112.0 (3)
C4—C3—C8118.8 (3)C13—C12—C11119.3 (3)
C4—C3—C2128.4 (3)C13—C12—H12120.4
C8—C3—C2112.8 (3)C11—C12—H12120.4
C5—C4—C3119.5 (3)C12—C13—C14121.0 (3)
C5—C4—H4120.3C12—C13—H13119.5
C3—C4—H4120.3C14—C13—H13119.5
C4—C5—C6120.7 (3)C15—C14—C13121.1 (3)
C4—C5—H5119.6C15—C14—H14119.5
C6—C5—H5119.6C13—C14—H14119.5
C7—C6—C5121.0 (3)C14—C15—C16118.0 (3)
C7—C6—H6119.5C14—C15—H15121.0
C5—C6—H6119.5C16—C15—H15121.0
C6—C7—C8118.4 (3)C15—C16—C11121.6 (3)
C6—C7—H7120.8C15—C16—S2126.5 (2)
C8—C7—H7120.8C11—C16—S2111.9 (2)
C7—C8—C3121.7 (3)O1—C17—C1121.1 (3)
C7—C8—S1125.7 (2)O1—C17—C9120.8 (3)
C3—C8—S1112.6 (2)C1—C17—C9118.1 (3)
C10—C9—C17129.5 (3)
C8—S1—C1—C20.1 (2)C9—C10—C11—C12176.5 (3)
C8—S1—C1—C17173.4 (2)C9—C10—C11—C162.0 (4)
C17—C1—C2—C3171.8 (3)C16—C11—C12—C131.2 (4)
S1—C1—C2—C30.8 (3)C10—C11—C12—C13179.5 (3)
C1—C2—C3—C4177.0 (3)C11—C12—C13—C140.7 (4)
C1—C2—C3—C81.3 (3)C12—C13—C14—C151.3 (5)
C8—C3—C4—C50.6 (4)C13—C14—C15—C160.0 (4)
C2—C3—C4—C5178.8 (3)C14—C15—C16—C111.9 (4)
C3—C4—C5—C60.5 (5)C14—C15—C16—S2176.8 (3)
C4—C5—C6—C70.2 (5)C12—C11—C16—C152.5 (4)
C5—C6—C7—C80.0 (4)C10—C11—C16—C15178.9 (3)
C6—C7—C8—C30.1 (4)C12—C11—C16—S2176.4 (2)
C6—C7—C8—S1177.2 (2)C10—C11—C16—S22.3 (3)
C4—C3—C8—C70.4 (4)C9—S2—C16—C15179.7 (3)
C2—C3—C8—C7178.9 (3)C9—S2—C16—C111.5 (2)
C4—C3—C8—S1177.3 (2)C2—C1—C17—O1154.8 (3)
C2—C3—C8—S11.2 (3)S1—C1—C17—O117.6 (4)
C1—S1—C8—C7178.2 (3)C2—C1—C17—C924.8 (4)
C1—S1—C8—C30.6 (2)S1—C1—C17—C9162.8 (2)
C16—S2—C9—C100.4 (2)C10—C9—C17—O1145.8 (3)
C16—S2—C9—C17175.1 (2)S2—C9—C17—O127.9 (4)
C17—C9—C10—C11173.1 (3)C10—C9—C17—C134.5 (5)
S2—C9—C10—C110.8 (3)S2—C9—C17—C1151.7 (2)
Hydrogen-bond geometry (Å, º) top
Cg4 and Cg2 are the centroids of the C9–C11/C16/S2 and C11–C16 rings, respectively; see Fig. 1(a).
D—H···AD—HH···AD···AD—H···A
C13—H13···O1i0.952.663.385 (3)134
C5—H5···Cg4ii0.952.903.694 (11)142
C10—H10···Cg2iii0.952.703.324 (12)124
Symmetry codes: (i) x+1/2, y+3/2, z; (ii) x, y1/2, z1/2; (iii) x+2, y+3/2, z+1/2.
(II) 1,1-Bis(benzo[b]thiophen-2-yl)-3-(trimethylsilyl)prop-2-yn-1-ol top
Crystal data top
C22H20OS2SiDx = 1.319 Mg m3
Mr = 392.59Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PnmaCell parameters from 4265 reflections
a = 19.3755 (5) Åθ = 2.4–33.4°
b = 17.0998 (4) ŵ = 0.34 mm1
c = 5.9656 (1) ÅT = 100 K
V = 1976.51 (8) Å3Block, colourless
Z = 40.58 × 0.44 × 0.19 mm
F(000) = 824
Data collection top
Bruker Kappa goniometer with an APEXII CCD area detector
diffractometer
1991 reflections with I > 2σ(I)
φ and ω scansRint = 0.016
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
θmax = 27.5°, θmin = 2.1°
Tmin = 0.828, Tmax = 0.939h = 240
4278 measured reflectionsk = 2217
2345 independent reflectionsl = 07
Refinement top
Refinement on F25 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.033H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.082 w = 1/[σ2(Fo2) + (0.0349P)2 + 0.8238P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
2345 reflectionsΔρmax = 0.31 e Å3
151 parametersΔρmin = 0.32 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Si10.49457 (2)0.75000.27063 (8)0.02004 (13)
S10.18173 (4)0.64903 (5)0.72862 (13)0.02106 (16)0.64
S1B0.25524 (8)0.62932 (10)0.2747 (2)0.0179 (3)0.36
C10.28354 (9)0.75000.5884 (3)0.0201 (4)
O10.29528 (7)0.75000.8252 (2)0.0271 (3)
H10.3138 (19)0.7922 (13)0.865 (6)0.052 (12)*0.5
C20.24199 (6)0.67730 (8)0.5315 (2)0.0181 (3)
C30.24152 (18)0.6339 (3)0.3446 (6)0.0244 (8)0.64
H30.27100.64450.22120.029*0.64
C3B0.1927 (3)0.6387 (3)0.6495 (8)0.0258 (13)0.36
H3B0.18160.65470.79760.031*0.36
C40.19188 (6)0.56845 (8)0.3441 (2)0.0240 (3)
C50.17515 (8)0.50935 (9)0.1933 (3)0.0316 (3)
H50.19880.50520.05440.038*
C60.12397 (9)0.45706 (9)0.2476 (3)0.0362 (4)
H60.11220.41670.14520.043*
C70.08915 (8)0.46275 (9)0.4518 (3)0.0358 (4)
H70.05370.42630.48600.043*
C80.10537 (7)0.52028 (9)0.6043 (3)0.0284 (3)
H80.08170.52370.74350.034*
C90.15736 (7)0.57358 (8)0.5501 (2)0.0210 (3)
C100.34990 (9)0.75000.4663 (3)0.0226 (4)
C110.40588 (9)0.75000.3796 (3)0.0210 (4)
C120.49279 (11)0.75000.0405 (3)0.0293 (4)
H12A0.48220.69720.09460.044*0.5
H12B0.53790.76630.09800.044*0.5
H12C0.45730.78650.09310.044*0.5
C130.53701 (10)0.83950 (13)0.3775 (3)0.0549 (6)
H13A0.51360.88570.31680.082*
H13B0.58550.83990.33080.082*
H13C0.53440.84030.54160.082*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Si10.0120 (2)0.0312 (3)0.0169 (2)0.0000.00120 (18)0.000
S10.0191 (3)0.0254 (3)0.0187 (4)0.0036 (2)0.0057 (3)0.0020 (3)
S1B0.0156 (7)0.0208 (5)0.0172 (7)0.0021 (5)0.0032 (5)0.0035 (5)
C10.0148 (8)0.0296 (10)0.0158 (8)0.0000.0005 (7)0.000
O10.0242 (7)0.0393 (9)0.0179 (7)0.0000.0056 (6)0.000
C20.0125 (5)0.0254 (7)0.0162 (6)0.0037 (5)0.0010 (4)0.0029 (5)
C30.0103 (15)0.0362 (16)0.027 (2)0.0044 (11)0.0061 (12)0.0153 (16)
C3B0.027 (3)0.039 (3)0.012 (3)0.0108 (19)0.005 (2)0.002 (2)
C40.0141 (6)0.0306 (7)0.0272 (7)0.0084 (5)0.0018 (5)0.0102 (6)
C50.0313 (8)0.0383 (8)0.0251 (7)0.0201 (6)0.0026 (6)0.0001 (6)
C60.0430 (9)0.0249 (7)0.0408 (9)0.0104 (7)0.0100 (7)0.0111 (7)
C70.0298 (8)0.0240 (7)0.0537 (10)0.0055 (6)0.0011 (7)0.0001 (7)
C80.0247 (7)0.0293 (7)0.0313 (8)0.0004 (5)0.0080 (6)0.0020 (6)
C90.0193 (6)0.0202 (6)0.0236 (7)0.0029 (5)0.0010 (5)0.0016 (5)
C100.0159 (9)0.0258 (10)0.0262 (10)0.0000.0013 (7)0.000
C110.0156 (8)0.0214 (9)0.0259 (9)0.0000.0012 (7)0.000
C120.0340 (11)0.0353 (12)0.0186 (9)0.0000.0003 (8)0.000
C130.0603 (12)0.0809 (14)0.0235 (8)0.0531 (11)0.0021 (8)0.0002 (9)
Geometric parameters (Å, º) top
Si1—C111.8372 (19)C3B—H3B0.9500
Si1—C13i1.8508 (17)C4—C51.391 (2)
Si1—C131.8508 (17)C4—C91.4018 (19)
Si1—C121.856 (2)C5—C61.374 (2)
S1—C21.7263 (14)C5—H50.9500
S1—C91.7384 (15)C6—C71.396 (2)
S1B—C41.662 (2)C6—H60.9500
S1B—C21.7567 (19)C7—C81.377 (2)
C1—O11.431 (2)C7—H70.9500
C1—C101.478 (3)C8—C91.3965 (19)
C1—C2i1.5193 (16)C8—H80.9500
C1—C21.5194 (16)C10—C111.202 (3)
O1—H10.839 (10)C12—H12A0.9800
C2—C31.339 (4)C12—H12B0.9800
C2—C3B1.358 (5)C12—H12C0.9800
C3—C41.476 (4)C13—H13A0.9800
C3—H30.9500C13—H13B0.9800
C3B—C91.435 (5)C13—H13C0.9800
C11—Si1—C13i107.08 (8)C6—C5—C4119.22 (14)
C11—Si1—C13107.08 (8)C6—C5—H5120.4
C13i—Si1—C13111.57 (15)C4—C5—H5120.4
C11—Si1—C12109.66 (10)C5—C6—C7120.62 (14)
C13i—Si1—C12110.66 (7)C5—C6—H6119.7
C13—Si1—C12110.66 (7)C7—C6—H6119.7
C2—S1—C988.52 (7)C8—C7—C6121.10 (14)
C4—S1B—C288.13 (9)C8—C7—H7119.4
O1—C1—C10110.37 (15)C6—C7—H7119.4
O1—C1—C2i107.74 (10)C7—C8—C9118.54 (14)
C10—C1—C2i110.54 (10)C7—C8—H8120.7
O1—C1—C2107.74 (10)C9—C8—H8120.7
C10—C1—C2110.55 (10)C8—C9—C4120.43 (13)
C2i—C1—C2109.82 (14)C8—C9—C3B139.0 (2)
C1—O1—H1110 (3)C4—C9—C3B100.6 (2)
C3—C2—C1130.00 (19)C8—C9—S1122.57 (11)
C3B—C2—C1130.9 (2)C4—C9—S1116.99 (11)
C3—C2—S1114.04 (17)C11—C10—C1176.0 (2)
C1—C2—S1115.81 (10)C10—C11—Si1175.22 (18)
C3B—C2—S1B109.1 (2)Si1—C12—H12A109.5
C1—C2—S1B119.97 (11)Si1—C12—H12B109.5
C2—C3—C4115.2 (2)H12A—C12—H12B109.5
C2—C3—H3122.4Si1—C12—H12C109.5
C4—C3—H3122.4H12A—C12—H12C109.5
C2—C3B—C9119.9 (4)H12B—C12—H12C109.5
C2—C3B—H3B120.0Si1—C13—H13A109.5
C9—C3B—H3B120.0Si1—C13—H13B109.5
C5—C4—C9120.08 (13)H13A—C13—H13B109.5
C5—C4—C3134.76 (17)Si1—C13—H13C109.5
C9—C4—C3105.16 (17)H13A—C13—H13C109.5
C5—C4—S1B117.77 (12)H13B—C13—H13C109.5
C9—C4—S1B122.12 (12)
O1—C1—C2—C3149.3 (3)C2—S1B—C4—C5179.69 (11)
C10—C1—C2—C328.6 (3)C2—S1B—C4—C91.93 (15)
C2i—C1—C2—C393.6 (3)C9—C4—C5—C60.9 (2)
O1—C1—C2—C3B33.6 (4)C3—C4—C5—C6179.2 (3)
C10—C1—C2—C3B154.3 (3)S1B—C4—C5—C6178.67 (13)
C2i—C1—C2—C3B83.5 (4)C4—C5—C6—C70.2 (2)
O1—C1—C2—S135.55 (14)C5—C6—C7—C80.5 (2)
C10—C1—C2—S1156.23 (11)C6—C7—C8—C90.4 (2)
C2i—C1—C2—S181.53 (15)C7—C8—C9—C40.2 (2)
O1—C1—C2—S1B146.19 (12)C7—C8—C9—C3B177.5 (4)
C10—C1—C2—S1B25.51 (17)C7—C8—C9—S1179.50 (12)
C2i—C1—C2—S1B96.73 (15)C5—C4—C9—C80.89 (19)
C9—S1—C2—C31.7 (2)C3—C4—C9—C8179.1 (2)
C9—S1—C2—C1177.66 (10)S1B—C4—C9—C8178.61 (13)
C4—S1B—C2—C3B3.4 (3)C5—C4—C9—C3B177.6 (3)
C4—S1B—C2—C1176.76 (11)S1B—C4—C9—C3B0.1 (3)
C1—C2—C3—C4177.48 (16)C5—C4—C9—S1179.80 (11)
S1—C2—C3—C42.2 (3)C3—C4—C9—S10.2 (2)
C1—C2—C3B—C9175.6 (2)C2—C3B—C9—C8178.9 (2)
S1B—C2—C3B—C94.6 (5)C2—C3B—C9—C43.1 (5)
C2—C3—C4—C5178.47 (17)C2—S1—C9—C8179.90 (12)
C2—C3—C4—C91.5 (3)C2—S1—C9—C40.82 (11)
Symmetry code: (i) x, y+3/2, z.
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the tiophene ring S1-C2-C3-C4-C9 and the benzene ring C4-C5-C6-C7-C8-C9, respectively; see Fig. 1b.
D—H···AD—HH···AD···AD—H···A
O1—H1···S1Bii0.84 (1)3.01 (4)3.4717 (19)117 (3)
C5—H5···S1Biii0.952.983.698 (2)134
Symmetry codes: (ii) x, y+3/2, z+1; (iii) x+1/2, y+1, z1/2.
(III) 1,1-Bis(benzo[b]thiophen-2-yl)prop-2-yn-1-ol top
Crystal data top
C19H12OS2F(000) = 664
Mr = 320.41Dx = 1.398 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9905 reflections
a = 9.4426 (3) Åθ = 3.0–40.2°
b = 19.5197 (6) ŵ = 0.35 mm1
c = 8.4323 (3) ÅT = 100 K
β = 101.539 (2)°Block, colourless
V = 1522.80 (9) Å30.42 × 0.39 × 0.24 mm
Z = 4
Data collection top
Bruker Kappa goniometer with an APEXII CCD area detector
diffractometer
2673 independent reflections
Radiation source: fine-focus sealed tube2567 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
φ and ω scansθmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 1111
Tmin = 0.868, Tmax = 0.921k = 2323
29484 measured reflectionsl = 1010
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)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.067H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0306P)2 + 0.8696P]
where P = (Fo2 + 2Fc2)/3
2673 reflections(Δ/σ)max = 0.001
210 parametersΔρmax = 0.52 e Å3
0 restraintsΔρmin = 0.25 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.87719 (10)0.14944 (5)0.63203 (12)0.0192 (2)
H10.92660.15030.55960.029*
S10.97650 (3)0.017169 (17)0.79264 (4)0.01571 (12)0.9648 (15)
S1B0.7585 (15)0.0370 (8)0.5105 (18)0.015 (4)*0.0352 (15)
S20.64591 (4)0.192805 (18)0.77639 (4)0.01717 (13)0.9250 (14)
S2B0.5665 (6)0.0391 (3)0.7355 (7)0.0115 (16)*0.0750 (14)
C10.83728 (14)0.02681 (7)0.62486 (15)0.0143 (3)
C20.8000 (2)0.03234 (10)0.5456 (2)0.0196 (4)
H20.72750.03550.44990.023*
C30.88078 (14)0.09012 (7)0.62027 (16)0.0164 (3)
C40.87069 (15)0.15970 (7)0.57672 (17)0.0211 (3)
H40.80360.17430.48330.025*
C50.95946 (16)0.20676 (7)0.67126 (18)0.0224 (3)
H50.95260.25390.64250.027*
C61.05924 (15)0.18589 (7)0.80878 (17)0.0212 (3)
H61.11890.21910.87230.025*
C71.07217 (14)0.11790 (7)0.85328 (17)0.0188 (3)
H71.14040.10370.94610.023*
C80.98227 (14)0.07031 (7)0.75833 (16)0.0155 (3)
C90.66590 (14)0.10978 (6)0.70964 (15)0.0143 (3)
C100.57303 (17)0.06420 (12)0.7569 (2)0.0207 (4)
H100.57130.01670.73200.025*
C110.47804 (14)0.09599 (7)0.84862 (16)0.0167 (3)
C120.36824 (15)0.06735 (8)0.91738 (17)0.0217 (3)
H120.34660.01990.90520.026*
C130.29201 (15)0.10872 (8)1.00276 (18)0.0256 (3)
H130.21810.08941.05030.031*
C140.32179 (16)0.17870 (8)1.02058 (17)0.0256 (3)
H140.26820.20621.08060.031*
C150.42754 (16)0.20856 (8)0.95255 (17)0.0234 (3)
H150.44650.25630.96340.028*
C160.50620 (14)0.16674 (7)0.86702 (16)0.0181 (3)
C170.76939 (14)0.09720 (7)0.59569 (16)0.0151 (3)
C180.68690 (15)0.10377 (7)0.42813 (16)0.0181 (3)
C190.61967 (16)0.11146 (8)0.29504 (18)0.0250 (3)
H190.56570.11760.18820.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0191 (5)0.0150 (5)0.0256 (5)0.0044 (4)0.0096 (4)0.0018 (4)
S10.01606 (19)0.01347 (19)0.0162 (2)0.00202 (12)0.00010 (13)0.00188 (12)
S20.0200 (2)0.0140 (2)0.0183 (2)0.00157 (13)0.00596 (14)0.00061 (13)
C10.0140 (6)0.0161 (7)0.0132 (6)0.0002 (5)0.0034 (5)0.0002 (5)
C20.0175 (10)0.0219 (9)0.0182 (9)0.0004 (8)0.0012 (8)0.0013 (7)
C30.0161 (6)0.0171 (7)0.0176 (7)0.0001 (5)0.0075 (5)0.0004 (5)
C40.0218 (7)0.0191 (7)0.0231 (7)0.0024 (5)0.0065 (6)0.0040 (6)
C50.0267 (7)0.0127 (6)0.0308 (8)0.0002 (6)0.0130 (6)0.0016 (6)
C60.0224 (7)0.0182 (7)0.0252 (7)0.0066 (5)0.0102 (6)0.0047 (6)
C70.0177 (7)0.0203 (7)0.0194 (7)0.0038 (5)0.0057 (5)0.0004 (5)
C80.0164 (6)0.0142 (6)0.0180 (6)0.0005 (5)0.0084 (5)0.0012 (5)
C90.0155 (6)0.0126 (6)0.0139 (6)0.0017 (5)0.0008 (5)0.0003 (5)
C100.0209 (9)0.0218 (10)0.0195 (9)0.0004 (7)0.0043 (6)0.0001 (8)
C110.0152 (6)0.0208 (7)0.0131 (6)0.0018 (5)0.0000 (5)0.0004 (5)
C120.0198 (7)0.0256 (7)0.0199 (7)0.0046 (6)0.0041 (6)0.0014 (6)
C130.0160 (7)0.0402 (9)0.0215 (7)0.0010 (6)0.0057 (6)0.0002 (6)
C140.0225 (7)0.0351 (8)0.0192 (7)0.0118 (6)0.0041 (6)0.0021 (6)
C150.0279 (7)0.0209 (7)0.0194 (7)0.0070 (6)0.0000 (6)0.0001 (6)
C160.0172 (6)0.0207 (7)0.0147 (6)0.0012 (5)0.0006 (5)0.0036 (5)
C170.0159 (6)0.0132 (6)0.0165 (6)0.0010 (5)0.0039 (5)0.0001 (5)
C180.0206 (7)0.0147 (6)0.0209 (7)0.0022 (5)0.0084 (6)0.0021 (5)
C190.0289 (8)0.0264 (8)0.0188 (8)0.0035 (6)0.0026 (6)0.0045 (6)
Geometric parameters (Å, º) top
O1—C171.4301 (16)C6—H60.9500
O1—H10.8400C7—C81.3974 (19)
S1—C81.7346 (13)C7—H70.9500
S1—C11.7381 (13)C9—C101.364 (2)
S1B—C11.658 (15)C9—C171.5213 (18)
S1B—C31.685 (15)C10—C111.437 (2)
S2—C161.7282 (14)C10—H100.9500
S2—C91.7381 (13)C11—C121.4016 (19)
S2B—C91.707 (6)C11—C161.409 (2)
S2B—C111.777 (6)C12—C131.377 (2)
C1—C21.345 (2)C12—H120.9500
C1—C171.5152 (18)C13—C141.397 (2)
C2—C31.435 (2)C13—H130.9500
C2—H20.9500C14—C151.377 (2)
C3—C41.4051 (19)C14—H140.9500
C3—C81.4060 (19)C15—C161.397 (2)
C4—C51.384 (2)C15—H150.9500
C4—H40.9500C17—C181.4762 (18)
C5—C61.401 (2)C18—C191.183 (2)
C5—H50.9500C19—H190.9500
C6—C71.378 (2)
C17—O1—H1109.5C10—C9—S2113.32 (12)
C8—S1—C190.85 (6)C17—C9—S2118.69 (9)
C1—S1B—C387.9 (7)S2B—C9—S2127.9 (2)
C16—S2—C990.61 (6)C9—C10—C11112.49 (19)
C9—S2B—C1183.8 (3)C9—C10—H10123.8
C2—C1—C17129.59 (14)C11—C10—H10123.8
C17—C1—S1B117.4 (5)C12—C11—C16118.97 (13)
C2—C1—S1113.06 (12)C12—C11—C10130.04 (15)
C17—C1—S1117.19 (9)C16—C11—C10110.99 (14)
S1B—C1—S1124.8 (5)C12—C11—S2B116.0 (2)
C1—C2—C3113.15 (18)C16—C11—S2B125.0 (2)
C1—C2—H2123.4C13—C12—C11119.32 (14)
C3—C2—H2123.4C13—C12—H12120.3
C4—C3—C8118.78 (12)C11—C12—H12120.3
C4—C3—C2130.00 (15)C12—C13—C14120.98 (14)
C8—C3—C2111.21 (14)C12—C13—H13119.5
C4—C3—S1B116.6 (5)C14—C13—H13119.5
C8—C3—S1B124.4 (5)C15—C14—C13121.09 (13)
C5—C4—C3119.31 (13)C15—C14—H14119.5
C5—C4—H4120.3C13—C14—H14119.5
C3—C4—H4120.3C14—C15—C16118.20 (14)
C4—C5—C6120.90 (13)C14—C15—H15120.9
C4—C5—H5119.5C16—C15—H15120.9
C6—C5—H5119.5C15—C16—C11121.42 (13)
C7—C6—C5120.93 (13)C15—C16—S2126.00 (11)
C7—C6—H6119.5C11—C16—S2112.57 (10)
C5—C6—H6119.5O1—C17—C18111.09 (11)
C6—C7—C8118.27 (13)O1—C17—C1110.60 (10)
C6—C7—H7120.9C18—C17—C1111.05 (11)
C8—C7—H7120.9O1—C17—C9105.61 (10)
C7—C8—C3121.80 (12)C18—C17—C9107.93 (10)
C7—C8—S1126.48 (11)C1—C17—C9110.38 (10)
C3—C8—S1111.71 (10)C19—C18—C17177.58 (15)
C10—C9—C17127.67 (14)C18—C19—H19180.0
C17—C9—S2B112.9 (2)
C3—S1B—C1—C216 (2)C9—C10—C11—C12179.65 (14)
C3—S1B—C1—C17176.2 (2)C9—C10—C11—C160.33 (17)
C3—S1B—C1—S15.3 (8)C9—C10—C11—S2B169.8 (10)
C8—S1—C1—C21.43 (12)C9—S2B—C11—C12179.18 (14)
C8—S1—C1—C17174.39 (10)C9—S2B—C11—C163.7 (3)
C8—S1—C1—S1B3.5 (6)C9—S2B—C11—C107.6 (7)
C17—C1—C2—C3173.51 (12)C16—C11—C12—C130.8 (2)
S1B—C1—C2—C3159 (3)C10—C11—C12—C13179.20 (14)
S1—C1—C2—C31.67 (18)S2B—C11—C12—C13178.1 (2)
C1—C2—C3—C4178.14 (14)C11—C12—C13—C140.5 (2)
C1—C2—C3—C81.03 (19)C12—C13—C14—C150.4 (2)
C1—C2—C3—S1B162 (2)C13—C14—C15—C161.0 (2)
C1—S1B—C3—C4179.5 (3)C14—C15—C16—C110.7 (2)
C1—S1B—C3—C86.0 (8)C14—C15—C16—S2178.37 (11)
C1—S1B—C3—C213.5 (18)C12—C11—C16—C150.25 (19)
C8—C3—C4—C50.62 (19)C10—C11—C16—C15179.77 (13)
C2—C3—C4—C5178.49 (15)S2B—C11—C16—C15177.3 (2)
S1B—C3—C4—C5174.2 (6)C12—C11—C16—S2179.39 (10)
C3—C4—C5—C60.3 (2)C10—C11—C16—S20.63 (15)
C4—C5—C6—C70.3 (2)S2B—C11—C16—S23.6 (3)
C5—C6—C7—C80.5 (2)C9—S2—C16—C15179.84 (12)
C6—C7—C8—C30.2 (2)C9—S2—C16—C111.06 (10)
C6—C7—C8—S1178.61 (10)C2—C1—C17—O1146.09 (15)
C4—C3—C8—C70.41 (19)S1B—C1—C17—O1149.5 (6)
C2—C3—C8—C7178.87 (13)S1—C1—C17—O138.90 (13)
S1B—C3—C8—C7174.0 (6)C2—C1—C17—C1822.3 (2)
C4—C3—C8—S1179.34 (10)S1B—C1—C17—C1825.7 (6)
C2—C3—C8—S10.06 (15)S1—C1—C17—C18162.72 (9)
S1B—C3—C8—S15.0 (6)C2—C1—C17—C997.40 (17)
C1—S1—C8—C7178.06 (12)S1B—C1—C17—C994.0 (6)
C1—S1—C8—C30.81 (10)S1—C1—C17—C977.61 (12)
C11—S2B—C9—C107.7 (7)C10—C9—C17—O1158.65 (13)
C11—S2B—C9—C17174.53 (13)S2B—C9—C17—O1159.4 (2)
C11—S2B—C9—S22.9 (3)S2—C9—C17—O128.18 (13)
C16—S2—C9—C101.27 (11)C10—C9—C17—C1882.46 (17)
C16—S2—C9—C17172.84 (10)S2B—C9—C17—C1881.8 (2)
C16—S2—C9—S2B1.6 (3)S2—C9—C17—C1890.71 (12)
C17—C9—C10—C11172.33 (12)C10—C9—C17—C139.07 (18)
S2B—C9—C10—C11169.8 (10)S2B—C9—C17—C139.8 (2)
S2—C9—C10—C111.15 (16)S2—C9—C17—C1147.75 (9)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of ring C3–C8 and ring C11-C-C16, respectively. Cg5 is the centroid of bond C7-C8; see Fig. 1c.
D—H···AD—HH···AD···AD—H···A
C6—H6···O1i0.952.573.2896 (17)133
C2—H2···S2Bii0.952.903.785 (6)155
O1—H1···Cg1iii0.842.693.5126 (10)166
C13—H13···Cg5iv0.952.823.7041 (14)155
C19—H19···Cg2v0.952.423.3614 (15)172
Symmetry codes: (i) x+2, y1/2, z+3/2; (ii) x+1, y, z+1; (iii) x+2, y, z+1; (iv) x+1, y, z+2; (v) x, y, z1.
Non-hydrogen-bonding interactions in the X-ray structures of (I)–(III). top
Cg3 is defined as the centroid of the C1–C3/C8/S1 thiophene ring (see Fig. 1).
InteractionsDistances (Å)
(I)(II)(III)
S1···O12.951 (3)2.861 (2)2.979 (2)
S2···O12.995 (8)2.845 (2)2.834 (2)
S1···Cg3i3.292 (3)
S1···S1ii3.501 (2)
Symmetry codes: (i) -x+1/2, y, z+1/2; (ii) -x+2, -y, -z+2.
Selected torsion angles (°) of the host conformations in the crystal structures of diaryl ketones (I) and (IV)–(VII) (Fig. 3) top
(I)(IV) (Benassi et al., 1989)(V) (Benassi et al., 1989)(VI) (Assadi et al., 2012)(VII) (Assadi et al., 2012)(VIII)a (Kutzke et al., 2000)
Interplanary angle (°)52.3 (3)46.137.884.0/77.951.154.4
Caryl—Cbridge—Caryl angle (°)118.11 (19)119.9120.9117.6/119.4120.6121.4
τ1 (°)-17.6 (4)-21.6-156.5139.1/137.6-25.028.1
τ2 (°)-27.9 (4)-21.6-156.5127.8/137.6-25.026.9
Note: (a) the stable polymorph at 223 K.
Selected torsion angles of the host conformations in the crystal structures of diaryl alcohols (II), (III), (IX) and (X) top
(II)(III)(IX) (Sieger & Werthmann, 2003)(IX).H2O (Banholzer et al., 2004)(X) (Meyerhöffer, 1970)
Interplanary angle (°)73.7 (8)84.9 (7)75.873.983.2
Caryl-Cbridge-Caryl angle (°)109.82 (14)110.38 (10)109.4109.5109.5
τ1 (°)35.55 (14)38.90 (10) /-149.5 (6)30.317.528.6
τ2 (°)-35.55 (14)28.18 (13) /-159.4 (2)169.6169.250.9
 

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