Crystal structures of functional building blocks derived from bis­(benzo[b]thio­phen-2-yl)methane

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 C_ar­yl—C_bridge—C_ar­yl 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.

Computing details

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

Crystal data

C17H10OS2	Dx = 1.478 Mg m^−3
Mr = 294.37	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Aba2	Cell parameters from 9041 reflections
a = 18.2186 (4) Å	θ = 2.3–35.0°
b = 20.0166 (4) Å	µ = 0.39 mm^−1
c = 7.2534 (2) Å	T = 100 K
V = 2645.13 (11) Å^3	Plate, colourless
Z = 8	0.35 × 0.34 × 0.10 mm
F(000) = 1216

Data collection

Bruker Kappa goniometer with an APEXII CCD area detector diffractometer	2282 reflections with I > 2σ(I)
phi and ω scans	Rint = 0.027
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	θmax = 25.0°, θmin = 2.0°
Tmin = 0.875, Tmax = 0.962	h = −18→21
13345 measured reflections	k = −23→23
2327 independent reflections	l = −8→8

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.025	w = 1/[σ^2(Fo^2) + (0.0377P)^2 + 3.9183P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.067	(Δ/σ)max = 0.001
S = 0.99	Δρmax = 0.42 e Å^−3
2327 reflections	Δρmin = −0.28 e Å^−3
181 parameters	Absolute structure: Flack x determined using 1027 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004)
1 restraint	Absolute structure parameter: 0.03 (2)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.75309 (12)	0.69981 (10)	1.0553 (3)	0.0223 (5)
S1	0.76808 (4)	0.55431 (4)	1.10846 (11)	0.01741 (19)
S2	0.84820 (4)	0.80488 (3)	0.88387 (12)	0.01572 (18)
C1	0.82947 (16)	0.60759 (14)	0.9991 (4)	0.0131 (6)
C2	0.88343 (17)	0.57534 (13)	0.8931 (4)	0.0153 (6)
H2	0.9214	0.5970	0.8259	0.018*
C3	0.87191 (15)	0.50314 (15)	0.9026 (4)	0.0141 (6)
C4	0.91093 (16)	0.45231 (15)	0.8115 (4)	0.0168 (6)
H4	0.9511	0.4632	0.7335	0.020*
C5	0.89051 (16)	0.38673 (15)	0.8364 (4)	0.0173 (7)
H5	0.9171	0.3523	0.7759	0.021*
C6	0.83086 (17)	0.37018 (15)	0.9502 (4)	0.0170 (6)
H6	0.8175	0.3246	0.9653	0.020*
C7	0.79150 (16)	0.41898 (15)	1.0403 (4)	0.0161 (6)
H7	0.7512	0.4077	1.1172	0.019*
C8	0.81227 (15)	0.48537 (14)	1.0158 (4)	0.0138 (6)
C9	0.87383 (16)	0.72714 (13)	0.9694 (4)	0.0129 (6)
C10	0.94780 (16)	0.72143 (14)	1.0019 (4)	0.0139 (6)
H10	0.9708	0.6821	1.0472	0.017*
C11	0.98609 (16)	0.78209 (14)	0.9592 (4)	0.0134 (6)
C12	1.06093 (17)	0.79737 (14)	0.9823 (4)	0.0152 (6)
H12	1.0937	0.7651	1.0316	0.018*
C13	1.08617 (17)	0.85968 (15)	0.9327 (4)	0.0170 (7)
H13	1.1366	0.8703	0.9493	0.020*
C14	1.03856 (18)	0.90768 (15)	0.8579 (4)	0.0186 (7)
H14	1.0574	0.9500	0.8224	0.022*
C15	0.96454 (17)	0.89438 (15)	0.8351 (4)	0.0161 (6)
H15	0.9324	0.9269	0.7844	0.019*
C16	0.93852 (15)	0.83169 (14)	0.8887 (4)	0.0136 (6)
C17	0.81376 (16)	0.67971 (15)	1.0119 (4)	0.0145 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0143 (10)	0.0178 (10)	0.0348 (14)	0.0010 (9)	0.0053 (10)	−0.0023 (10)
S1	0.0166 (3)	0.0166 (3)	0.0191 (4)	−0.0012 (3)	0.0029 (3)	0.0007 (3)
S2	0.0132 (3)	0.0129 (3)	0.0210 (4)	0.0014 (3)	−0.0003 (3)	0.0016 (3)
C1	0.0111 (13)	0.0164 (14)	0.0117 (15)	−0.0034 (11)	0.0003 (11)	0.0015 (12)
C2	0.0275 (16)	0.0070 (13)	0.0114 (14)	0.0034 (11)	−0.0136 (14)	−0.0020 (12)
C3	0.0131 (13)	0.0169 (14)	0.0121 (15)	−0.0016 (11)	−0.0040 (13)	0.0013 (12)
C4	0.0128 (14)	0.0233 (15)	0.0143 (15)	−0.0018 (12)	0.0010 (13)	−0.0016 (12)
C5	0.0155 (15)	0.0194 (15)	0.0169 (16)	0.0041 (12)	−0.0041 (12)	−0.0046 (12)
C6	0.0199 (15)	0.0129 (14)	0.0182 (15)	−0.0017 (12)	−0.0076 (13)	0.0008 (11)
C7	0.0128 (14)	0.0202 (15)	0.0152 (15)	−0.0023 (12)	−0.0022 (12)	0.0046 (12)
C8	0.0119 (14)	0.0178 (14)	0.0117 (14)	0.0001 (11)	−0.0022 (11)	0.0015 (12)
C9	0.0151 (14)	0.0105 (13)	0.0131 (14)	0.0012 (11)	0.0014 (11)	−0.0020 (11)
C10	0.0188 (14)	0.0124 (13)	0.0107 (15)	−0.0033 (12)	0.0000 (12)	−0.0002 (11)
C11	0.0167 (14)	0.0136 (13)	0.0101 (13)	0.0013 (11)	0.0007 (11)	−0.0014 (11)
C12	0.0159 (15)	0.0173 (14)	0.0123 (15)	0.0016 (11)	0.0004 (12)	−0.0012 (12)
C13	0.0147 (14)	0.0195 (15)	0.0167 (16)	−0.0046 (12)	−0.0015 (11)	−0.0058 (12)
C14	0.0243 (16)	0.0122 (13)	0.0193 (16)	−0.0054 (12)	0.0039 (12)	−0.0018 (12)
C15	0.0200 (15)	0.0115 (14)	0.0168 (16)	0.0013 (12)	0.0014 (12)	−0.0005 (11)
C16	0.0132 (13)	0.0140 (13)	0.0137 (13)	0.0016 (11)	0.0015 (12)	−0.0023 (13)
C17	0.0135 (15)	0.0162 (14)	0.0138 (15)	−0.0011 (11)	−0.0004 (11)	0.0011 (12)

Geometric parameters (Å, º)

O1—C17	1.217 (4)	C7—C8	1.393 (4)
S1—C8	1.733 (3)	C7—H7	0.9500
S1—C1	1.737 (3)	C9—C10	1.373 (4)
S2—C16	1.731 (3)	C9—C17	1.481 (4)
S2—C9	1.739 (3)	C10—C11	1.434 (4)
C1—C2	1.405 (4)	C10—H10	0.9500
C1—C17	1.475 (4)	C11—C12	1.407 (4)
C2—C3	1.462 (4)	C11—C16	1.414 (4)
C2—H2	0.9500	C12—C13	1.377 (4)
C3—C4	1.406 (4)	C12—H12	0.9500
C3—C8	1.408 (4)	C13—C14	1.404 (4)
C4—C5	1.376 (4)	C13—H13	0.9500
C4—H4	0.9500	C14—C15	1.384 (4)
C5—C6	1.405 (4)	C14—H14	0.9500
C5—H5	0.9500	C15—C16	1.397 (4)
C6—C7	1.376 (4)	C15—H15	0.9500
C6—H6	0.9500
C8—S1—C1	90.71 (14)	C10—C9—S2	113.5 (2)
C16—S2—C9	90.85 (14)	C17—C9—S2	116.7 (2)
C2—C1—C17	128.3 (3)	C9—C10—C11	111.7 (3)
C2—C1—S1	114.7 (2)	C9—C10—H10	124.1
C17—C1—S1	116.6 (2)	C11—C10—H10	124.1
C1—C2—C3	109.1 (3)	C12—C11—C16	119.0 (3)
C1—C2—H2	125.4	C12—C11—C10	129.0 (3)
C3—C2—H2	125.4	C16—C11—C10	112.0 (3)
C4—C3—C8	118.8 (3)	C13—C12—C11	119.3 (3)
C4—C3—C2	128.4 (3)	C13—C12—H12	120.4
C8—C3—C2	112.8 (3)	C11—C12—H12	120.4
C5—C4—C3	119.5 (3)	C12—C13—C14	121.0 (3)
C5—C4—H4	120.3	C12—C13—H13	119.5
C3—C4—H4	120.3	C14—C13—H13	119.5
C4—C5—C6	120.7 (3)	C15—C14—C13	121.1 (3)
C4—C5—H5	119.6	C15—C14—H14	119.5
C6—C5—H5	119.6	C13—C14—H14	119.5
C7—C6—C5	121.0 (3)	C14—C15—C16	118.0 (3)
C7—C6—H6	119.5	C14—C15—H15	121.0
C5—C6—H6	119.5	C16—C15—H15	121.0
C6—C7—C8	118.4 (3)	C15—C16—C11	121.6 (3)
C6—C7—H7	120.8	C15—C16—S2	126.5 (2)
C8—C7—H7	120.8	C11—C16—S2	111.9 (2)
C7—C8—C3	121.7 (3)	O1—C17—C1	121.1 (3)
C7—C8—S1	125.7 (2)	O1—C17—C9	120.8 (3)
C3—C8—S1	112.6 (2)	C1—C17—C9	118.1 (3)
C10—C9—C17	129.5 (3)
C8—S1—C1—C2	−0.1 (2)	C9—C10—C11—C12	176.5 (3)
C8—S1—C1—C17	173.4 (2)	C9—C10—C11—C16	−2.0 (4)
C17—C1—C2—C3	−171.8 (3)	C16—C11—C12—C13	−1.2 (4)
S1—C1—C2—C3	0.8 (3)	C10—C11—C12—C13	−179.5 (3)
C1—C2—C3—C4	177.0 (3)	C11—C12—C13—C14	−0.7 (4)
C1—C2—C3—C8	−1.3 (3)	C12—C13—C14—C15	1.3 (5)
C8—C3—C4—C5	−0.6 (4)	C13—C14—C15—C16	0.0 (4)
C2—C3—C4—C5	−178.8 (3)	C14—C15—C16—C11	−1.9 (4)
C3—C4—C5—C6	0.5 (5)	C14—C15—C16—S2	176.8 (3)
C4—C5—C6—C7	−0.2 (5)	C12—C11—C16—C15	2.5 (4)
C5—C6—C7—C8	0.0 (4)	C10—C11—C16—C15	−178.9 (3)
C6—C7—C8—C3	−0.1 (4)	C12—C11—C16—S2	−176.4 (2)
C6—C7—C8—S1	177.2 (2)	C10—C11—C16—S2	2.3 (3)
C4—C3—C8—C7	0.4 (4)	C9—S2—C16—C15	179.7 (3)
C2—C3—C8—C7	178.9 (3)	C9—S2—C16—C11	−1.5 (2)
C4—C3—C8—S1	−177.3 (2)	C2—C1—C17—O1	154.8 (3)
C2—C3—C8—S1	1.2 (3)	S1—C1—C17—O1	−17.6 (4)
C1—S1—C8—C7	−178.2 (3)	C2—C1—C17—C9	−24.8 (4)
C1—S1—C8—C3	−0.6 (2)	S1—C1—C17—C9	162.8 (2)
C16—S2—C9—C10	0.4 (2)	C10—C9—C17—O1	145.8 (3)
C16—S2—C9—C17	175.1 (2)	S2—C9—C17—O1	−27.9 (4)
C17—C9—C10—C11	−173.1 (3)	C10—C9—C17—C1	−34.5 (5)
S2—C9—C10—C11	0.8 (3)	S2—C9—C17—C1	151.7 (2)

Hydrogen-bond geometry (Å, º)

Cg4 and Cg2 are the centroids of the C9–C11/C16/S2 and C11–C16 rings, respectively; see Fig. 1(a).

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1^i	0.95	2.66	3.385 (3)	134
C5—H5···Cg4^ii	0.95	2.90	3.694 (11)	142
C10—H10···Cg2^iii	0.95	2.70	3.324 (12)	124

Symmetry codes: (i) x+1/2, −y+3/2, z; (ii) x, y−1/2, z−1/2; (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

Crystal data

C22H20OS2Si	Dx = 1.319 Mg m^−3
Mr = 392.59	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pnma	Cell parameters from 4265 reflections
a = 19.3755 (5) Å	θ = 2.4–33.4°
b = 17.0998 (4) Å	µ = 0.34 mm^−1
c = 5.9656 (1) Å	T = 100 K
V = 1976.51 (8) Å^3	Block, colourless
Z = 4	0.58 × 0.44 × 0.19 mm
F(000) = 824

Data collection

Bruker Kappa goniometer with an APEXII CCD area detector diffractometer	1991 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.016
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	θmax = 27.5°, θmin = 2.1°
Tmin = 0.828, Tmax = 0.939	h = −24→0
4278 measured reflections	k = −22→17
2345 independent reflections	l = 0→7

Refinement

Refinement on F^2	5 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.082	w = 1/[σ^2(Fo^2) + (0.0349P)^2 + 0.8238P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
2345 reflections	Δρmax = 0.31 e Å^−3
151 parameters	Δρmin = −0.32 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Si1	0.49457 (2)	0.7500	0.27063 (8)	0.02004 (13)
S1	0.18173 (4)	0.64903 (5)	0.72862 (13)	0.02106 (16)	0.64
S1B	0.25524 (8)	0.62932 (10)	0.2747 (2)	0.0179 (3)	0.36
C1	0.28354 (9)	0.7500	0.5884 (3)	0.0201 (4)
O1	0.29528 (7)	0.7500	0.8252 (2)	0.0271 (3)
H1	0.3138 (19)	0.7922 (13)	0.865 (6)	0.052 (12)*	0.5
C2	0.24199 (6)	0.67730 (8)	0.5315 (2)	0.0181 (3)
C3	0.24152 (18)	0.6339 (3)	0.3446 (6)	0.0244 (8)	0.64
H3	0.2710	0.6445	0.2212	0.029*	0.64
C3B	0.1927 (3)	0.6387 (3)	0.6495 (8)	0.0258 (13)	0.36
H3B	0.1816	0.6547	0.7976	0.031*	0.36
C4	0.19188 (6)	0.56845 (8)	0.3441 (2)	0.0240 (3)
C5	0.17515 (8)	0.50935 (9)	0.1933 (3)	0.0316 (3)
H5	0.1988	0.5052	0.0544	0.038*
C6	0.12397 (9)	0.45706 (9)	0.2476 (3)	0.0362 (4)
H6	0.1122	0.4167	0.1452	0.043*
C7	0.08915 (8)	0.46275 (9)	0.4518 (3)	0.0358 (4)
H7	0.0537	0.4263	0.4860	0.043*
C8	0.10537 (7)	0.52028 (9)	0.6043 (3)	0.0284 (3)
H8	0.0817	0.5237	0.7435	0.034*
C9	0.15736 (7)	0.57358 (8)	0.5501 (2)	0.0210 (3)
C10	0.34990 (9)	0.7500	0.4663 (3)	0.0226 (4)
C11	0.40588 (9)	0.7500	0.3796 (3)	0.0210 (4)
C12	0.49279 (11)	0.7500	−0.0405 (3)	0.0293 (4)
H12A	0.4822	0.6972	−0.0946	0.044*	0.5
H12B	0.5379	0.7663	−0.0980	0.044*	0.5
H12C	0.4573	0.7865	−0.0931	0.044*	0.5
C13	0.53701 (10)	0.83950 (13)	0.3775 (3)	0.0549 (6)
H13A	0.5136	0.8857	0.3168	0.082*
H13B	0.5855	0.8399	0.3308	0.082*
H13C	0.5344	0.8403	0.5416	0.082*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Si1	0.0120 (2)	0.0312 (3)	0.0169 (2)	0.000	0.00120 (18)	0.000
S1	0.0191 (3)	0.0254 (3)	0.0187 (4)	−0.0036 (2)	0.0057 (3)	0.0020 (3)
S1B	0.0156 (7)	0.0208 (5)	0.0172 (7)	−0.0021 (5)	0.0032 (5)	0.0035 (5)
C1	0.0148 (8)	0.0296 (10)	0.0158 (8)	0.000	−0.0005 (7)	0.000
O1	0.0242 (7)	0.0393 (9)	0.0179 (7)	0.000	−0.0056 (6)	0.000
C2	0.0125 (5)	0.0254 (7)	0.0162 (6)	0.0037 (5)	0.0010 (4)	0.0029 (5)
C3	0.0103 (15)	0.0362 (16)	0.027 (2)	0.0044 (11)	0.0061 (12)	0.0153 (16)
C3B	0.027 (3)	0.039 (3)	0.012 (3)	0.0108 (19)	0.005 (2)	−0.002 (2)
C4	0.0141 (6)	0.0306 (7)	0.0272 (7)	0.0084 (5)	0.0018 (5)	0.0102 (6)
C5	0.0313 (8)	0.0383 (8)	0.0251 (7)	0.0201 (6)	0.0026 (6)	0.0001 (6)
C6	0.0430 (9)	0.0249 (7)	0.0408 (9)	0.0104 (7)	−0.0100 (7)	−0.0111 (7)
C7	0.0298 (8)	0.0240 (7)	0.0537 (10)	−0.0055 (6)	0.0011 (7)	0.0001 (7)
C8	0.0247 (7)	0.0293 (7)	0.0313 (8)	−0.0004 (5)	0.0080 (6)	0.0020 (6)
C9	0.0193 (6)	0.0202 (6)	0.0236 (7)	0.0029 (5)	−0.0010 (5)	0.0016 (5)
C10	0.0159 (9)	0.0258 (10)	0.0262 (10)	0.000	−0.0013 (7)	0.000
C11	0.0156 (8)	0.0214 (9)	0.0259 (9)	0.000	−0.0012 (7)	0.000
C12	0.0340 (11)	0.0353 (12)	0.0186 (9)	0.000	0.0003 (8)	0.000
C13	0.0603 (12)	0.0809 (14)	0.0235 (8)	−0.0531 (11)	−0.0021 (8)	0.0002 (9)

Geometric parameters (Å, º)

Si1—C11	1.8372 (19)	C3B—H3B	0.9500
Si1—C13^i	1.8508 (17)	C4—C5	1.391 (2)
Si1—C13	1.8508 (17)	C4—C9	1.4018 (19)
Si1—C12	1.856 (2)	C5—C6	1.374 (2)
S1—C2	1.7263 (14)	C5—H5	0.9500
S1—C9	1.7384 (15)	C6—C7	1.396 (2)
S1B—C4	1.662 (2)	C6—H6	0.9500
S1B—C2	1.7567 (19)	C7—C8	1.377 (2)
C1—O1	1.431 (2)	C7—H7	0.9500
C1—C10	1.478 (3)	C8—C9	1.3965 (19)
C1—C2^i	1.5193 (16)	C8—H8	0.9500
C1—C2	1.5194 (16)	C10—C11	1.202 (3)
O1—H1	0.839 (10)	C12—H12A	0.9800
C2—C3	1.339 (4)	C12—H12B	0.9800
C2—C3B	1.358 (5)	C12—H12C	0.9800
C3—C4	1.476 (4)	C13—H13A	0.9800
C3—H3	0.9500	C13—H13B	0.9800
C3B—C9	1.435 (5)	C13—H13C	0.9800
C11—Si1—C13^i	107.08 (8)	C6—C5—C4	119.22 (14)
C11—Si1—C13	107.08 (8)	C6—C5—H5	120.4
C13^i—Si1—C13	111.57 (15)	C4—C5—H5	120.4
C11—Si1—C12	109.66 (10)	C5—C6—C7	120.62 (14)
C13^i—Si1—C12	110.66 (7)	C5—C6—H6	119.7
C13—Si1—C12	110.66 (7)	C7—C6—H6	119.7
C2—S1—C9	88.52 (7)	C8—C7—C6	121.10 (14)
C4—S1B—C2	88.13 (9)	C8—C7—H7	119.4
O1—C1—C10	110.37 (15)	C6—C7—H7	119.4
O1—C1—C2^i	107.74 (10)	C7—C8—C9	118.54 (14)
C10—C1—C2^i	110.54 (10)	C7—C8—H8	120.7
O1—C1—C2	107.74 (10)	C9—C8—H8	120.7
C10—C1—C2	110.55 (10)	C8—C9—C4	120.43 (13)
C2^i—C1—C2	109.82 (14)	C8—C9—C3B	139.0 (2)
C1—O1—H1	110 (3)	C4—C9—C3B	100.6 (2)
C3—C2—C1	130.00 (19)	C8—C9—S1	122.57 (11)
C3B—C2—C1	130.9 (2)	C4—C9—S1	116.99 (11)
C3—C2—S1	114.04 (17)	C11—C10—C1	176.0 (2)
C1—C2—S1	115.81 (10)	C10—C11—Si1	175.22 (18)
C3B—C2—S1B	109.1 (2)	Si1—C12—H12A	109.5
C1—C2—S1B	119.97 (11)	Si1—C12—H12B	109.5
C2—C3—C4	115.2 (2)	H12A—C12—H12B	109.5
C2—C3—H3	122.4	Si1—C12—H12C	109.5
C4—C3—H3	122.4	H12A—C12—H12C	109.5
C2—C3B—C9	119.9 (4)	H12B—C12—H12C	109.5
C2—C3B—H3B	120.0	Si1—C13—H13A	109.5
C9—C3B—H3B	120.0	Si1—C13—H13B	109.5
C5—C4—C9	120.08 (13)	H13A—C13—H13B	109.5
C5—C4—C3	134.76 (17)	Si1—C13—H13C	109.5
C9—C4—C3	105.16 (17)	H13A—C13—H13C	109.5
C5—C4—S1B	117.77 (12)	H13B—C13—H13C	109.5
C9—C4—S1B	122.12 (12)
O1—C1—C2—C3	−149.3 (3)	C2—S1B—C4—C5	−179.69 (11)
C10—C1—C2—C3	−28.6 (3)	C2—S1B—C4—C9	−1.93 (15)
C2^i—C1—C2—C3	93.6 (3)	C9—C4—C5—C6	0.9 (2)
O1—C1—C2—C3B	33.6 (4)	C3—C4—C5—C6	−179.2 (3)
C10—C1—C2—C3B	154.3 (3)	S1B—C4—C5—C6	178.67 (13)
C2^i—C1—C2—C3B	−83.5 (4)	C4—C5—C6—C7	−0.2 (2)
O1—C1—C2—S1	35.55 (14)	C5—C6—C7—C8	−0.5 (2)
C10—C1—C2—S1	156.23 (11)	C6—C7—C8—C9	0.4 (2)
C2^i—C1—C2—S1	−81.53 (15)	C7—C8—C9—C4	0.2 (2)
O1—C1—C2—S1B	−146.19 (12)	C7—C8—C9—C3B	−177.5 (4)
C10—C1—C2—S1B	−25.51 (17)	C7—C8—C9—S1	179.50 (12)
C2^i—C1—C2—S1B	96.73 (15)	C5—C4—C9—C8	−0.89 (19)
C9—S1—C2—C3	1.7 (2)	C3—C4—C9—C8	179.1 (2)
C9—S1—C2—C1	177.66 (10)	S1B—C4—C9—C8	−178.61 (13)
C4—S1B—C2—C3B	3.4 (3)	C5—C4—C9—C3B	177.6 (3)
C4—S1B—C2—C1	−176.76 (11)	S1B—C4—C9—C3B	−0.1 (3)
C1—C2—C3—C4	−177.48 (16)	C5—C4—C9—S1	179.80 (11)
S1—C2—C3—C4	−2.2 (3)	C3—C4—C9—S1	−0.2 (2)
C1—C2—C3B—C9	175.6 (2)	C2—C3B—C9—C8	−178.9 (2)
S1B—C2—C3B—C9	−4.6 (5)	C2—C3B—C9—C4	3.1 (5)
C2—C3—C4—C5	−178.47 (17)	C2—S1—C9—C8	179.90 (12)
C2—C3—C4—C9	1.5 (3)	C2—S1—C9—C4	−0.82 (11)

Symmetry code: (i) x, −y+3/2, z.

Hydrogen-bond geometry (Å, º)

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···A	D—H	H···A	D···A	D—H···A
O1—H1···S1B^ii	0.84 (1)	3.01 (4)	3.4717 (19)	117 (3)
C5—H5···S1B^iii	0.95	2.98	3.698 (2)	134

Symmetry codes: (ii) x, −y+3/2, z+1; (iii) −x+1/2, −y+1, z−1/2.

(III) 1,1-Bis(benzo[b]thiophen-2-yl)prop-2-yn-1-ol

Crystal data

C19H12OS2	F(000) = 664
Mr = 320.41	Dx = 1.398 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9905 reflections
a = 9.4426 (3) Å	θ = 3.0–40.2°
b = 19.5197 (6) Å	µ = 0.35 mm^−1
c = 8.4323 (3) Å	T = 100 K
β = 101.539 (2)°	Block, colourless
V = 1522.80 (9) Å^3	0.42 × 0.39 × 0.24 mm
Z = 4

Data collection

Bruker Kappa goniometer with an APEXII CCD area detector diffractometer	2673 independent reflections
Radiation source: fine-focus sealed tube	2567 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −11→11
Tmin = 0.868, Tmax = 0.921	k = −23→23
29484 measured reflections	l = −10→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.067	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0306P)^2 + 0.8696P] where P = (Fo^2 + 2Fc^2)/3
2673 reflections	(Δ/σ)max = 0.001
210 parameters	Δρmax = 0.52 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.87719 (10)	0.14944 (5)	0.63203 (12)	0.0192 (2)
H1	0.9266	0.1503	0.5596	0.029*
S1	0.97650 (3)	0.017169 (17)	0.79264 (4)	0.01571 (12)	0.9648 (15)
S1B	0.7585 (15)	−0.0370 (8)	0.5105 (18)	0.015 (4)*	0.0352 (15)
S2	0.64591 (4)	0.192805 (18)	0.77639 (4)	0.01717 (13)	0.9250 (14)
S2B	0.5665 (6)	0.0391 (3)	0.7355 (7)	0.0115 (16)*	0.0750 (14)
C1	0.83728 (14)	0.02681 (7)	0.62486 (15)	0.0143 (3)
C2	0.8000 (2)	−0.03234 (10)	0.5456 (2)	0.0196 (4)
H2	0.7275	−0.0355	0.4499	0.023*
C3	0.88078 (14)	−0.09012 (7)	0.62027 (16)	0.0164 (3)
C4	0.87069 (15)	−0.15970 (7)	0.57672 (17)	0.0211 (3)
H4	0.8036	−0.1743	0.4833	0.025*
C5	0.95946 (16)	−0.20676 (7)	0.67126 (18)	0.0224 (3)
H5	0.9526	−0.2539	0.6425	0.027*
C6	1.05924 (15)	−0.18589 (7)	0.80878 (17)	0.0212 (3)
H6	1.1189	−0.2191	0.8723	0.025*
C7	1.07217 (14)	−0.11790 (7)	0.85328 (17)	0.0188 (3)
H7	1.1404	−0.1037	0.9461	0.023*
C8	0.98227 (14)	−0.07031 (7)	0.75833 (16)	0.0155 (3)
C9	0.66590 (14)	0.10978 (6)	0.70964 (15)	0.0143 (3)
C10	0.57303 (17)	0.06420 (12)	0.7569 (2)	0.0207 (4)
H10	0.5713	0.0167	0.7320	0.025*
C11	0.47804 (14)	0.09599 (7)	0.84862 (16)	0.0167 (3)
C12	0.36824 (15)	0.06735 (8)	0.91738 (17)	0.0217 (3)
H12	0.3466	0.0199	0.9052	0.026*
C13	0.29201 (15)	0.10872 (8)	1.00276 (18)	0.0256 (3)
H13	0.2181	0.0894	1.0503	0.031*
C14	0.32179 (16)	0.17870 (8)	1.02058 (17)	0.0256 (3)
H14	0.2682	0.2062	1.0806	0.031*
C15	0.42754 (16)	0.20856 (8)	0.95255 (17)	0.0234 (3)
H15	0.4465	0.2563	0.9634	0.028*
C16	0.50620 (14)	0.16674 (7)	0.86702 (16)	0.0181 (3)
C17	0.76939 (14)	0.09720 (7)	0.59569 (16)	0.0151 (3)
C18	0.68690 (15)	0.10377 (7)	0.42813 (16)	0.0181 (3)
C19	0.61967 (16)	0.11146 (8)	0.29504 (18)	0.0250 (3)
H19	0.5657	0.1176	0.1882	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0191 (5)	0.0150 (5)	0.0256 (5)	−0.0044 (4)	0.0096 (4)	−0.0018 (4)
S1	0.01606 (19)	0.01347 (19)	0.0162 (2)	0.00202 (12)	−0.00010 (13)	−0.00188 (12)
S2	0.0200 (2)	0.0140 (2)	0.0183 (2)	0.00157 (13)	0.00596 (14)	0.00061 (13)
C1	0.0140 (6)	0.0161 (7)	0.0132 (6)	0.0002 (5)	0.0034 (5)	0.0002 (5)
C2	0.0175 (10)	0.0219 (9)	0.0182 (9)	−0.0004 (8)	0.0012 (8)	−0.0013 (7)
C3	0.0161 (6)	0.0171 (7)	0.0176 (7)	−0.0001 (5)	0.0075 (5)	−0.0004 (5)
C4	0.0218 (7)	0.0191 (7)	0.0231 (7)	−0.0024 (5)	0.0065 (6)	−0.0040 (6)
C5	0.0267 (7)	0.0127 (6)	0.0308 (8)	−0.0002 (6)	0.0130 (6)	−0.0016 (6)
C6	0.0224 (7)	0.0182 (7)	0.0252 (7)	0.0066 (5)	0.0102 (6)	0.0047 (6)
C7	0.0177 (7)	0.0203 (7)	0.0194 (7)	0.0038 (5)	0.0057 (5)	0.0004 (5)
C8	0.0164 (6)	0.0142 (6)	0.0180 (6)	0.0005 (5)	0.0084 (5)	−0.0012 (5)
C9	0.0155 (6)	0.0126 (6)	0.0139 (6)	0.0017 (5)	0.0008 (5)	0.0003 (5)
C10	0.0209 (9)	0.0218 (10)	0.0195 (9)	−0.0004 (7)	0.0043 (6)	−0.0001 (8)
C11	0.0152 (6)	0.0208 (7)	0.0131 (6)	0.0018 (5)	0.0000 (5)	0.0004 (5)
C12	0.0198 (7)	0.0256 (7)	0.0199 (7)	−0.0046 (6)	0.0041 (6)	−0.0014 (6)
C13	0.0160 (7)	0.0402 (9)	0.0215 (7)	−0.0010 (6)	0.0057 (6)	−0.0002 (6)
C14	0.0225 (7)	0.0351 (8)	0.0192 (7)	0.0118 (6)	0.0041 (6)	−0.0021 (6)
C15	0.0279 (7)	0.0209 (7)	0.0194 (7)	0.0070 (6)	0.0000 (6)	−0.0001 (6)
C16	0.0172 (6)	0.0207 (7)	0.0147 (6)	0.0012 (5)	−0.0006 (5)	0.0036 (5)
C17	0.0159 (6)	0.0132 (6)	0.0165 (6)	−0.0010 (5)	0.0039 (5)	0.0001 (5)
C18	0.0206 (7)	0.0147 (6)	0.0209 (7)	0.0022 (5)	0.0084 (6)	0.0021 (5)
C19	0.0289 (8)	0.0264 (8)	0.0188 (8)	0.0035 (6)	0.0026 (6)	0.0045 (6)

Geometric parameters (Å, º)

O1—C17	1.4301 (16)	C6—H6	0.9500
O1—H1	0.8400	C7—C8	1.3974 (19)
S1—C8	1.7346 (13)	C7—H7	0.9500
S1—C1	1.7381 (13)	C9—C10	1.364 (2)
S1B—C1	1.658 (15)	C9—C17	1.5213 (18)
S1B—C3	1.685 (15)	C10—C11	1.437 (2)
S2—C16	1.7282 (14)	C10—H10	0.9500
S2—C9	1.7381 (13)	C11—C12	1.4016 (19)
S2B—C9	1.707 (6)	C11—C16	1.409 (2)
S2B—C11	1.777 (6)	C12—C13	1.377 (2)
C1—C2	1.345 (2)	C12—H12	0.9500
C1—C17	1.5152 (18)	C13—C14	1.397 (2)
C2—C3	1.435 (2)	C13—H13	0.9500
C2—H2	0.9500	C14—C15	1.377 (2)
C3—C4	1.4051 (19)	C14—H14	0.9500
C3—C8	1.4060 (19)	C15—C16	1.397 (2)
C4—C5	1.384 (2)	C15—H15	0.9500
C4—H4	0.9500	C17—C18	1.4762 (18)
C5—C6	1.401 (2)	C18—C19	1.183 (2)
C5—H5	0.9500	C19—H19	0.9500
C6—C7	1.378 (2)
C17—O1—H1	109.5	C10—C9—S2	113.32 (12)
C8—S1—C1	90.85 (6)	C17—C9—S2	118.69 (9)
C1—S1B—C3	87.9 (7)	S2B—C9—S2	127.9 (2)
C16—S2—C9	90.61 (6)	C9—C10—C11	112.49 (19)
C9—S2B—C11	83.8 (3)	C9—C10—H10	123.8
C2—C1—C17	129.59 (14)	C11—C10—H10	123.8
C17—C1—S1B	117.4 (5)	C12—C11—C16	118.97 (13)
C2—C1—S1	113.06 (12)	C12—C11—C10	130.04 (15)
C17—C1—S1	117.19 (9)	C16—C11—C10	110.99 (14)
S1B—C1—S1	124.8 (5)	C12—C11—S2B	116.0 (2)
C1—C2—C3	113.15 (18)	C16—C11—S2B	125.0 (2)
C1—C2—H2	123.4	C13—C12—C11	119.32 (14)
C3—C2—H2	123.4	C13—C12—H12	120.3
C4—C3—C8	118.78 (12)	C11—C12—H12	120.3
C4—C3—C2	130.00 (15)	C12—C13—C14	120.98 (14)
C8—C3—C2	111.21 (14)	C12—C13—H13	119.5
C4—C3—S1B	116.6 (5)	C14—C13—H13	119.5
C8—C3—S1B	124.4 (5)	C15—C14—C13	121.09 (13)
C5—C4—C3	119.31 (13)	C15—C14—H14	119.5
C5—C4—H4	120.3	C13—C14—H14	119.5
C3—C4—H4	120.3	C14—C15—C16	118.20 (14)
C4—C5—C6	120.90 (13)	C14—C15—H15	120.9
C4—C5—H5	119.5	C16—C15—H15	120.9
C6—C5—H5	119.5	C15—C16—C11	121.42 (13)
C7—C6—C5	120.93 (13)	C15—C16—S2	126.00 (11)
C7—C6—H6	119.5	C11—C16—S2	112.57 (10)
C5—C6—H6	119.5	O1—C17—C18	111.09 (11)
C6—C7—C8	118.27 (13)	O1—C17—C1	110.60 (10)
C6—C7—H7	120.9	C18—C17—C1	111.05 (11)
C8—C7—H7	120.9	O1—C17—C9	105.61 (10)
C7—C8—C3	121.80 (12)	C18—C17—C9	107.93 (10)
C7—C8—S1	126.48 (11)	C1—C17—C9	110.38 (10)
C3—C8—S1	111.71 (10)	C19—C18—C17	177.58 (15)
C10—C9—C17	127.67 (14)	C18—C19—H19	180.0
C17—C9—S2B	112.9 (2)
C3—S1B—C1—C2	16 (2)	C9—C10—C11—C12	179.65 (14)
C3—S1B—C1—C17	−176.2 (2)	C9—C10—C11—C16	−0.33 (17)
C3—S1B—C1—S1	−5.3 (8)	C9—C10—C11—S2B	169.8 (10)
C8—S1—C1—C2	−1.43 (12)	C9—S2B—C11—C12	−179.18 (14)
C8—S1—C1—C17	174.39 (10)	C9—S2B—C11—C16	3.7 (3)
C8—S1—C1—S1B	3.5 (6)	C9—S2B—C11—C10	−7.6 (7)
C17—C1—C2—C3	−173.51 (12)	C16—C11—C12—C13	−0.8 (2)
S1B—C1—C2—C3	−159 (3)	C10—C11—C12—C13	179.20 (14)
S1—C1—C2—C3	1.67 (18)	S2B—C11—C12—C13	−178.1 (2)
C1—C2—C3—C4	178.14 (14)	C11—C12—C13—C14	0.5 (2)
C1—C2—C3—C8	−1.03 (19)	C12—C13—C14—C15	0.4 (2)
C1—C2—C3—S1B	162 (2)	C13—C14—C15—C16	−1.0 (2)
C1—S1B—C3—C4	−179.5 (3)	C14—C15—C16—C11	0.7 (2)
C1—S1B—C3—C8	6.0 (8)	C14—C15—C16—S2	−178.37 (11)
C1—S1B—C3—C2	−13.5 (18)	C12—C11—C16—C15	0.25 (19)
C8—C3—C4—C5	0.62 (19)	C10—C11—C16—C15	−179.77 (13)
C2—C3—C4—C5	−178.49 (15)	S2B—C11—C16—C15	177.3 (2)
S1B—C3—C4—C5	−174.2 (6)	C12—C11—C16—S2	179.39 (10)
C3—C4—C5—C6	−0.3 (2)	C10—C11—C16—S2	−0.63 (15)
C4—C5—C6—C7	−0.3 (2)	S2B—C11—C16—S2	−3.6 (3)
C5—C6—C7—C8	0.5 (2)	C9—S2—C16—C15	−179.84 (12)
C6—C7—C8—C3	−0.2 (2)	C9—S2—C16—C11	1.06 (10)
C6—C7—C8—S1	178.61 (10)	C2—C1—C17—O1	−146.09 (15)
C4—C3—C8—C7	−0.41 (19)	S1B—C1—C17—O1	−149.5 (6)
C2—C3—C8—C7	178.87 (13)	S1—C1—C17—O1	38.90 (13)
S1B—C3—C8—C7	174.0 (6)	C2—C1—C17—C18	−22.3 (2)
C4—C3—C8—S1	−179.34 (10)	S1B—C1—C17—C18	−25.7 (6)
C2—C3—C8—S1	−0.06 (15)	S1—C1—C17—C18	162.72 (9)
S1B—C3—C8—S1	−5.0 (6)	C2—C1—C17—C9	97.40 (17)
C1—S1—C8—C7	−178.06 (12)	S1B—C1—C17—C9	94.0 (6)
C1—S1—C8—C3	0.81 (10)	S1—C1—C17—C9	−77.61 (12)
C11—S2B—C9—C10	7.7 (7)	C10—C9—C17—O1	−158.65 (13)
C11—S2B—C9—C17	−174.53 (13)	S2B—C9—C17—O1	−159.4 (2)
C11—S2B—C9—S2	−2.9 (3)	S2—C9—C17—O1	28.18 (13)
C16—S2—C9—C10	−1.27 (11)	C10—C9—C17—C18	82.46 (17)
C16—S2—C9—C17	172.84 (10)	S2B—C9—C17—C18	81.8 (2)
C16—S2—C9—S2B	1.6 (3)	S2—C9—C17—C18	−90.71 (12)
C17—C9—C10—C11	−172.33 (12)	C10—C9—C17—C1	−39.07 (18)
S2B—C9—C10—C11	−169.8 (10)	S2B—C9—C17—C1	−39.8 (2)
S2—C9—C10—C11	1.15 (16)	S2—C9—C17—C1	147.75 (9)

Hydrogen-bond geometry (Å, º)

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···A	D—H	H···A	D···A	D—H···A
C6—H6···O1^i	0.95	2.57	3.2896 (17)	133
C2—H2···S2B^ii	0.95	2.90	3.785 (6)	155
O1—H1···Cg1^iii	0.84	2.69	3.5126 (10)	166
C13—H13···Cg5^iv	0.95	2.82	3.7041 (14)	155
C19—H19···Cg2^v	0.95	2.42	3.3614 (15)	172

Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) −x+1, −y, −z+1; (iii) −x+2, −y, −z+1; (iv) −x+1, −y, −z+2; (v) x, y, z−1.