research communications
The crystal structures of six (2E)-3-aryl-1-(5-halogenothiophen-2-yl)prop-2-en-1-ones
aDepartment of Physics, Government First Grade College, Kumta 581 343, India, Research and Development Centre, Bharathiar University, Coimbatore 641 046, India, bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, cDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and dSchool of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, Scotland
*Correspondence e-mail: jpjasinski@hotmail.com
The structures of six E)-1-(5-chlorothiophen-2-yl)-3-(4-ethylphenyl)prop-2-en-1-one, C15H13ClOS, (I), and (2E)-1-(5-bromothiophen-2-yl)-3-(4-ethylphenyl)prop-2-en-1-one, C15H13BrOS, (II), are isostructural in P-1, while (2E)-1-(5-chlorothiophen-2-yl)-3-(4-ethoxyphenyl)prop-2-en-1-one, C15H13ClO2S, (III), and (2E)-1-(5-bromothiophen-2-yl)-3-(4-ethoxyphenyl)prop-2-en-1-one C15H13BrO2S, (IV), are isostructural in P21/c. There are no hydrogen bonds of any kind in the structures of compounds (I) and (II), but in the structures of compounds (III) and (IV), the molecules are linked into C(7) chains by means of C—H⋯O hydrogen bonds. In the structure of (2E)-3-(4-bromophenyl)-1-(5-chlorothiophen-2-yl)prop-2-en-1-one, C13H8BrClOS, (V), there are again no hydrogen bonds nor π–π stacking interactions but in that of (2E)-1-(5-bromothiophen-2-yl)-3-(3-methoxyphenyl)prop-2-en-1-one, C14H11BrO2S, (VI), the molecules are linked into C(5) chains by C—H⋯O hydrogen bonds. In each of compounds (I)–(VI), the molecular skeletons are close to planarity, and there are short halogen⋯halogen contacts in the structures of compounds (II) and (V) and a short Br⋯O contact in the structure of compound (VI). Comparisons are made with the structures of some similar compounds.
containing 5-halogenothiophen-2-yl substituents are reported: (21. Chemical context
et al., 2008; Kumar et al., 2013a), anticancer (Shin et al., 2013), antifungal (Domínguez et al., 2001; Kumar et al., 2013a,b), antimalarial (Li et al., 1995) and antitubercular (Lin et al., 2002) activity. In addition, chalcone derivatives are also important materials in photonic applications because of their excellent blue-light transmittance and good crystallization ability (Goto et al., 1991; Uchida et al.,1998; Indira et al., 2002; Sarojini et al., 2006). In a continuation of our work on containing a thiophen moiety (Naik et al., 2015), six new of this type, compounds (I)–(VI) (Figs. 1–6) have now been synthesized and we report herein on their molecular structures and supramolecular assembly. Compounds (I)–(VI) were all prepared using condensation reactions, under basic conditions, between 2-acetyl-5-halogenothiophens and substituted benzaldehydes.
are important constituents of many natural products, and they are abundant in edible plants where they are considered to be precursors of and They display a wide range of pharmacological properties including antibacterial (Tang2. Structural commentary
Compounds (I) and (II) are isostructural in P, while compounds (III) and (IV) are isostructural in P21/c. Although the unit-cell dimensions for compound (V) are similar to those for compounds (I) and (II), a detailed comparison of the atomic coordinates for compounds (I), (II) and (V) indicates that there is no simple relationship between those of (I) and (II) on the one hand and those of (V) on the other. Although compound (VI) crystallizes in the same as compounds (III) and (IV), the unit-cell dimensions for (VI) are very different from those for (III) and (IV).
Although the molecules of compounds (I)–(VI) all lie in general positions, the non-H atoms of the molecular skeletons are quite close to being co-planar, apart from the terminal C atoms of the ethyl groups in compounds (I)–(IV), as shown by the dihedral angles in Table 1. The values of these angles demonstrate the very close conformational similarity between the molecules of the three compounds, (I), (II) and (V), which crystallize in P, and between those of the three compounds, (III), (IV) and (VI), in P21/c. In the molecules of each of (I)–(V), the 5-halogenothienyl unit adopts the same orientation, with S11—C12—C1—C2 torsion angles close to 180° (Table 1). There is no evidence in any of the structures reported here for orientational disorder of the type commonly observed with otherwise unsubstituted thienyl units; this is presumably a direct consequence of the presence of the halogen substituent.
In each of compounds (III), (IV) and (VI), all of which carry an alkoxy substituent, the atom C37 (Figs. 3, 4 and 6) lies close to the plane of the adjacent aryl ring: the displacements of the atoms C37 from these planes are 0.117 (3), 0.097 (4) and 0.186 (4) Å, respectively. Consistent with these observations, the corresponding pairs of exocyclic C—C—O angles (Table 1) differ significantly, as typically found for alkoxybenzenes with near-planar molecular skeletons (Seip & Seip, 1973; Ferguson et al., 1996). Whereas the whole ethoxy group in each of compounds (III) and (IV) is nearly coplanar with the adjacent aryl ring, this is far from the case for compounds (I) and (II) (Table 1, Figs. 1–4).
The bond distances in compounds (I)–(VI) all lie within the usual ranges (Allen et al., 1987).
3. Supramolecular interactions
There are no direction-specific intermolecular interactions in the structure of compound (I); hydrogen bonds of C—H⋯O and C—H⋯π types are absent, as are π–π stacking interactions. Hydrogen bonds and π–π stacking interactions are also absent from the structure of compound (II), but in this structure there is a short intermolecular Br⋯Br contact, with parameters Br15⋯Br15i = 3.4917 (5) Å and C15—Br15⋯Br15i = 151.37 (8)° [symmetry code: (i) −x + 1, −y + 1, −z + 2]. The Br ⋯Br distance is significantly shorter than the van der Waals contact distance of 3.70 Å (Bondi, 1964; Rowland & Taylor, 1996), while the observed C—Br⋯Br angle is consistent with the results of a database analysis of such contacts (Ramasubbu et al., 1986), which found that such angles were, in general, clustered around 165°.
In each of compounds (III) and (IV), a single C—H⋯O hydrogen bond having the carbonyl O atom as the acceptor (Table 2) links molecules related by c-glide symmetry into zigzag C(7) (Bernstein et al., 1995) chains running parallel to the [001] direction (Fig. 7). Two chains of this type, related to one another by inversion, pass through each but there are no direction-specific interactions between adjacent chains: in particular there are no short intermolecular Br⋯Br contacts in the structure of compound (IV), thus differing in this respect from compound (II).
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There are neither hydrogen bonds nor π–π stacking interactions in the structure of compound (V). However, the structure contains a fairly short intermolecular Cl⋯Cl contact, although, rather surprisingly, there are no short contacts of either Br⋯Br or Br⋯Cl types. For the contact C15—Cl15⋯Cl15ii [symmetry code: (ii) −x + 1, −y, −z + 2], the geometrical parameters are Cl⋯Clii = 3.4825 (11) Å and C—Cl⋯Clii = 167.83 (10)°. The Cl⋯Cl distances is thus just at the van der Waals contact distance 3.48 Å (Rowland & Taylor, 1996) and so this contact cannot be regarded as structurally significant: however, it may be noted that the angle C—Cl⋯Clii is entirely consistent with the results of a database analysis (Ramasubbu et al., 1986).
A single C—H⋯O hydrogen bond (Table 2) links the molecules of compound (VI) which are related by the 21 screw axis along (, y, ) into a C(5) chain running parallel to the [010] direction (Fig. 8). Two chains of this type, related to one another by inversion, pass through each but there are no direction-specific interactions between adjacent chains. Not only are C—H⋯π hydrogen bonds and π–π stacking interactions absent from the of compound (VI), but neither are there any short Br⋯Br contacts of the type found in compound (II). There is however a short intermolecular Br⋯O contact with parameters Br15⋯O33iii = 2.9770 (16) Å and C15—Br15⋯O33iii = 167.21 (7)° [symmetry code: (iii) x − , y, z + 1].
All of the compounds reported here crystallize either in P or in P21/c, and there appear to be some interesting connections between the space groups and the nature of the direction-specific intermolecular interactions manifested in the various structures. Thus although all six of the compounds described here contain carbonyl groups, only in compounds (III), (IV) and (VI) do the O atoms of these units participate as acceptors in C—H⋯O hydrogen bonds: these happen to be the three examples which crystallize in P21/c. Of the three 5-bromothienyl derivatives reported here, a short Br⋯Br contact occurs only in compound (II), the only example of this group which crystallizes in P.
4. Database survey
The structures of a number of (2E)-3-aryl-1-(5-chlorothiophen-2-yl)-prop-2-en-1-one derivatives closely related to compounds (I)–(VI) have been reported recently, usually in the form of brief reports on single structures in which no comparisons with related compounds were made, and sometimes with little or no mention of the supramolecular assembly. It is thus of interest briefly to compare the supramolecular assembly in these compounds with that in compounds (I)–(VI). Compound (VII) (see Scheme below) is isomeric with compound (V), and these two compounds differ only in the exchange of the halogen location. Despite this, they are not isomorphous as compound (VII) crystallizes in P21/c (Kavitha et al., 2013), as opposed to P for compound (V). There are two C—H⋯π contacts in the structure of compound (VII), but both of these have long H⋯D distances and small D—H⋯A angles, and so are probably not structurally significant. There is, however, a short intermolecular Br⋯Cl contact for which the Br⋯Cl distance of 3.5746 (11) Å (not 3.698 (1) Å as stated in the original report), is larger than the sum, 3.55 Å (Rowland & Taylor (1996), of the van der Waals radii.
For compound (VIII) (Vepuri et al., 2012), which provides a genuine example of Z′ = 2 in Cc (Baur & Kassner, 1992; Marsh, 1997, 2004), there are no significant direction interactions in the structure: in particular there are neither C—H⋯O hydrogen bonds nor short Br⋯Br contacts. Compounds (IX) (Prabhu et al., 2011b) and (X) (Prabhu et al., 2014) are isostructural, and (X) was described as forming chains built from two independent C—H⋯O hydrogen bonds. However, one of these contacts involves a methyl C—H bond and the other has a C—H⋯O angle of only 130° (cf. Wood et al., 2009), so that neither can be regarded as structurally significant. On the other hand the structure of (IX) contains a significant aromatic π–π stacking interaction between the phenyl rings of inversion-related molecules, although this was apparently overlooked in the original report. The phenyl rings of the molecules at (x, y, z) and (−x + 2, −y + 2, −z + 2) are strictly parallel with an interplanar spacing of 3.5113 (8) Å: the ring centroid separation is 3.6535 (11) Å, corresponding to a ring-centroid offset of 1.009 (2) Å, so leading to the formation of a centrosymmetric π-stacked dimer (Fig. 9).
The original report on compound (XI) (Sunitha et al., 2012) provides no analysis or description of the supramolecular assembly. Examination of the original atomic coordinates shows firstly that molecules related by a c-glide plane are linked by a nearly linear C—H⋯O hydrogen bond, forming a C(6) chain running parallel to the [001] direction, and secondly that inversion-related pairs of molecules are linked by a π–π stacking interaction involving the phenyl rings of the molecules at (x, y, z) and (−x + 1, −y + 1, −z), with interplanar spacing 3.4465 (10) Å, ring-centroid separation 3.749 (3) Å and ring-centroid offset 1.475 (3) Å. The combined effect of these two types of interaction is the formation of a sheet lying parallel to (100); see Fig. 10.
There are two intermolecular C—H⋯O contacts in the structure of compound (XII) which were described (Prabhu et al., 2011a) as joining the molecules into chains: however, for these two contacts the H⋯O distances, 2.68 and 2.71 Å, both exceed the sum of the van der Waals radii, 2.65 Å (Rowland & Taylor, 1996), so that these contacts certainly cannot be regarded as hydrogen bonds. Simple C(11) chains are formed in the structure of compound (XIII) built from C—H⋯O hydrogen bonds (Vepuri et al., 2011), but there are no short Br⋯Br contacts in either of (XI) and (XIII).
5. Synthesis and crystallization
For the synthesis of each compound, an equimolar mixture (0.01 mol of each component) of the appropriate 2-acetyl-5-halogenothiophen and the appropriately-substituted benzaldehyde was dissolved in a mixture of methanol (20 ml) and aqueous sodium hydroxide solution (5 ml of 30% w/v solution). The mixtures were all stirred at ambient temperature for 4 h, and then poured into ice-cold water (250 ml): the resulting solid products were collected by filtration and dried in air at 323 K. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation, at ambient temperature and in the presence of air, of solutions in acetone: melting points: (I) 384 K, (II) 423 K, (III) 415 K. (IV) 403 K, (V) 423 K and (VI) 390 K.
6. Refinement
Crystal data, data collection and structure . All H atoms were located in difference Fourier maps and subsequently treated as riding atoms in geometrically idealized positions with C—H distances 0.95 Å (alkenyl, aromatic and heteroaromatic), 0.98 Å (CH3) or 0.99 Å (CH2), and with Uiso(H) = kUeq(C), where k = 1.5 for the methyl groups, which were permitted to rotate but not to tilt, and 1.2 for other H atoms. The low-angle reflections (,2,1) for compound (III) and (2,1,2) for compound (VI), which had been attenuated by the beam stop, were omitted from the final refinements for these structures.
details are summarized in Table 3
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Supporting information
https://doi.org/10.1107/S2056989015015534/su5193sup1.cif
contains datablocks global, I, II, III, IV, V, VI. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015015534/su5193Isup2.hkl
Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989015015534/su5193IIsup3.hkl
Structure factors: contains datablock III. DOI: https://doi.org/10.1107/S2056989015015534/su5193IIIsup4.hkl
Structure factors: contains datablock IV. DOI: https://doi.org/10.1107/S2056989015015534/su5193IVsup5.hkl
Structure factors: contains datablock V. DOI: https://doi.org/10.1107/S2056989015015534/su5193Vsup6.hkl
Structure factors: contains datablock VI. DOI: https://doi.org/10.1107/S2056989015015534/su5193VIsup7.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989015015534/su5193Isup8.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989015015534/su5193IIsup9.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989015015534/su5193IIIsup10.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989015015534/su5193IVsup11.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989015015534/su5193Vsup12.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989015015534/su5193VIsup13.cml
For all compounds, data collection: CrysAlis PRO (Agilent, 2012); cell
CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 and PLATON.C15H13ClOS | Z = 2 |
Mr = 276.76 | F(000) = 288 |
Triclinic, P1 | Dx = 1.390 Mg m−3 |
a = 6.0154 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.6358 (5) Å | Cell parameters from 4320 reflections |
c = 14.0548 (9) Å | θ = 3.4–32.6° |
α = 74.428 (5)° | µ = 0.43 mm−1 |
β = 88.225 (6)° | T = 173 K |
γ = 70.417 (6)° | Needle, colourless |
V = 661.23 (8) Å3 | 0.58 × 0.32 × 0.29 mm |
Agilent Eos Gemini diffractometer | 3262 reflections with I > 2σ(I) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.028 |
ω scans | θmax = 30.0°, θmin = 3.4° |
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012) | h = −7→8 |
Tmin = 0.750, Tmax = 0.883 | k = −11→12 |
6596 measured reflections | l = −19→19 |
3861 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.042 | w = 1/[σ2(Fo2) + (0.0573P)2 + 0.1938P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.119 | (Δ/σ)max = 0.001 |
S = 1.06 | Δρmax = 0.57 e Å−3 |
3861 reflections | Δρmin = −0.34 e Å−3 |
165 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.019 (5) |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.6919 (3) | 0.25997 (18) | 0.55004 (11) | 0.0231 (3) | |
O1 | 0.9071 (2) | 0.23082 (16) | 0.54537 (9) | 0.0327 (3) | |
C2 | 0.5468 (3) | 0.22773 (19) | 0.47997 (11) | 0.0238 (3) | |
H2 | 0.3798 | 0.2644 | 0.4831 | 0.029* | |
C3 | 0.6465 (3) | 0.14771 (18) | 0.41211 (11) | 0.0240 (3) | |
H3 | 0.8144 | 0.1055 | 0.4146 | 0.029* | |
S11 | 0.73786 (7) | 0.36484 (5) | 0.71337 (3) | 0.02478 (12) | |
C12 | 0.5682 (3) | 0.33247 (18) | 0.62836 (11) | 0.0213 (3) | |
C13 | 0.3333 (3) | 0.38074 (19) | 0.64782 (11) | 0.0240 (3) | |
H13 | 0.2138 | 0.3719 | 0.6091 | 0.029* | |
C14 | 0.2884 (3) | 0.4450 (2) | 0.73162 (11) | 0.0261 (3) | |
H14 | 0.1363 | 0.4845 | 0.7557 | 0.031* | |
C15 | 0.4915 (3) | 0.44302 (19) | 0.77353 (11) | 0.0236 (3) | |
Cl15 | 0.51445 (8) | 0.51198 (6) | 0.87520 (3) | 0.03470 (13) | |
C31 | 0.5211 (3) | 0.11904 (18) | 0.33424 (11) | 0.0224 (3) | |
C32 | 0.6526 (3) | 0.03119 (19) | 0.26918 (11) | 0.0263 (3) | |
H32 | 0.8199 | −0.0166 | 0.2795 | 0.032* | |
C33 | 0.5411 (3) | 0.0132 (2) | 0.18973 (12) | 0.0282 (3) | |
H33 | 0.6337 | −0.0465 | 0.1464 | 0.034* | |
C34 | 0.2974 (3) | 0.08041 (19) | 0.17246 (11) | 0.0264 (3) | |
C35 | 0.1656 (3) | 0.1642 (2) | 0.23891 (12) | 0.0292 (3) | |
H35 | −0.0019 | 0.2096 | 0.2291 | 0.035* | |
C36 | 0.2743 (3) | 0.1824 (2) | 0.31864 (12) | 0.0272 (3) | |
H36 | 0.1806 | 0.2385 | 0.3632 | 0.033* | |
C37 | 0.1759 (4) | 0.0704 (2) | 0.08306 (13) | 0.0344 (4) | |
H37A | 0.0277 | 0.0476 | 0.1022 | 0.041* | |
H37B | 0.2794 | −0.0259 | 0.0594 | 0.041* | |
C38 | 0.1187 (4) | 0.2345 (3) | −0.00031 (15) | 0.0464 (5) | |
H38A | 0.0401 | 0.2232 | −0.0568 | 0.070* | |
H38B | 0.2653 | 0.2563 | −0.0204 | 0.070* | |
H38C | 0.0138 | 0.3299 | 0.0225 | 0.070* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0237 (7) | 0.0227 (6) | 0.0224 (7) | −0.0066 (5) | −0.0010 (5) | −0.0066 (5) |
O1 | 0.0225 (5) | 0.0439 (7) | 0.0342 (6) | −0.0081 (5) | 0.0011 (5) | −0.0188 (5) |
C2 | 0.0226 (7) | 0.0257 (7) | 0.0240 (7) | −0.0077 (6) | −0.0001 (5) | −0.0085 (6) |
C3 | 0.0240 (7) | 0.0246 (7) | 0.0234 (7) | −0.0078 (6) | −0.0003 (5) | −0.0067 (5) |
S11 | 0.02067 (19) | 0.0317 (2) | 0.0247 (2) | −0.00974 (15) | −0.00090 (13) | −0.01084 (15) |
C12 | 0.0220 (7) | 0.0211 (6) | 0.0211 (6) | −0.0077 (5) | −0.0015 (5) | −0.0057 (5) |
C13 | 0.0218 (7) | 0.0289 (7) | 0.0248 (7) | −0.0108 (6) | −0.0001 (5) | −0.0102 (6) |
C14 | 0.0223 (7) | 0.0310 (7) | 0.0279 (8) | −0.0099 (6) | 0.0043 (6) | −0.0122 (6) |
C15 | 0.0272 (7) | 0.0247 (6) | 0.0211 (7) | −0.0104 (6) | 0.0009 (5) | −0.0077 (5) |
Cl15 | 0.0419 (2) | 0.0431 (2) | 0.0267 (2) | −0.01768 (19) | 0.00181 (16) | −0.01764 (17) |
C31 | 0.0260 (7) | 0.0221 (6) | 0.0194 (6) | −0.0084 (6) | 0.0016 (5) | −0.0061 (5) |
C32 | 0.0276 (7) | 0.0250 (7) | 0.0251 (7) | −0.0061 (6) | 0.0031 (6) | −0.0086 (6) |
C33 | 0.0358 (8) | 0.0268 (7) | 0.0261 (7) | −0.0114 (6) | 0.0069 (6) | −0.0137 (6) |
C34 | 0.0373 (9) | 0.0252 (7) | 0.0220 (7) | −0.0161 (6) | 0.0021 (6) | −0.0080 (6) |
C35 | 0.0271 (8) | 0.0344 (8) | 0.0314 (8) | −0.0129 (7) | 0.0024 (6) | −0.0144 (7) |
C36 | 0.0268 (7) | 0.0322 (7) | 0.0269 (7) | −0.0109 (6) | 0.0052 (6) | −0.0145 (6) |
C37 | 0.0424 (10) | 0.0422 (9) | 0.0284 (8) | −0.0219 (8) | 0.0006 (7) | −0.0155 (7) |
C38 | 0.0593 (13) | 0.0413 (10) | 0.0343 (10) | −0.0091 (9) | −0.0109 (9) | −0.0118 (8) |
C1—O1 | 1.2361 (19) | C31—C36 | 1.401 (2) |
C1—C12 | 1.471 (2) | C32—C33 | 1.390 (2) |
C1—C2 | 1.474 (2) | C32—H32 | 0.9500 |
C2—C3 | 1.337 (2) | C33—C34 | 1.386 (2) |
C2—H2 | 0.9500 | C33—H33 | 0.9500 |
C3—C31 | 1.466 (2) | C34—C35 | 1.399 (2) |
C3—H3 | 0.9500 | C34—C37 | 1.509 (2) |
S11—C15 | 1.7105 (16) | C35—C36 | 1.385 (2) |
S11—C12 | 1.7300 (14) | C35—H35 | 0.9500 |
C12—C13 | 1.374 (2) | C36—H36 | 0.9500 |
C13—C14 | 1.414 (2) | C37—C38 | 1.519 (3) |
C13—H13 | 0.9500 | C37—H37A | 0.9900 |
C14—C15 | 1.365 (2) | C37—H37B | 0.9900 |
C14—H14 | 0.9500 | C38—H38A | 0.9800 |
C15—Cl15 | 1.7146 (15) | C38—H38B | 0.9800 |
C31—C32 | 1.401 (2) | C38—H38C | 0.9800 |
O1—C1—C12 | 119.59 (13) | C33—C32—H32 | 119.6 |
O1—C1—C2 | 123.61 (14) | C31—C32—H32 | 119.6 |
C12—C1—C2 | 116.79 (13) | C34—C33—C32 | 121.34 (14) |
C3—C2—C1 | 121.02 (14) | C34—C33—H33 | 119.3 |
C3—C2—H2 | 119.5 | C32—C33—H33 | 119.3 |
C1—C2—H2 | 119.5 | C33—C34—C35 | 117.93 (14) |
C2—C3—C31 | 126.11 (14) | C33—C34—C37 | 121.69 (15) |
C2—C3—H3 | 116.9 | C35—C34—C37 | 120.34 (16) |
C31—C3—H3 | 116.9 | C36—C35—C34 | 121.33 (16) |
C15—S11—C12 | 90.59 (7) | C36—C35—H35 | 119.3 |
C13—C12—C1 | 131.06 (13) | C34—C35—H35 | 119.3 |
C13—C12—S11 | 111.68 (11) | C35—C36—C31 | 120.66 (14) |
C1—C12—S11 | 117.26 (11) | C35—C36—H36 | 119.7 |
C12—C13—C14 | 112.81 (13) | C31—C36—H36 | 119.7 |
C12—C13—H13 | 123.6 | C34—C37—C38 | 111.86 (14) |
C14—C13—H13 | 123.6 | C34—C37—H37A | 109.2 |
C15—C14—C13 | 111.43 (14) | C38—C37—H37A | 109.2 |
C15—C14—H14 | 124.3 | C34—C37—H37B | 109.2 |
C13—C14—H14 | 124.3 | C38—C37—H37B | 109.2 |
C14—C15—S11 | 113.49 (11) | H37A—C37—H37B | 107.9 |
C14—C15—Cl15 | 126.35 (13) | C37—C38—H38A | 109.5 |
S11—C15—Cl15 | 120.16 (9) | C37—C38—H38B | 109.5 |
C32—C31—C36 | 117.93 (14) | H38A—C38—H38B | 109.5 |
C32—C31—C3 | 119.01 (14) | C37—C38—H38C | 109.5 |
C36—C31—C3 | 122.99 (13) | H38A—C38—H38C | 109.5 |
C33—C32—C31 | 120.75 (15) | H38B—C38—H38C | 109.5 |
O1—C1—C2—C3 | 6.9 (2) | C12—S11—C15—Cl15 | −179.17 (9) |
C12—C1—C2—C3 | −173.77 (13) | C2—C3—C31—C32 | −179.46 (15) |
C1—C2—C3—C31 | −175.39 (13) | C2—C3—C31—C36 | 3.6 (2) |
O1—C1—C12—C13 | 177.79 (15) | C36—C31—C32—C33 | 2.2 (2) |
C2—C1—C12—C13 | −1.6 (2) | C3—C31—C32—C33 | −174.90 (13) |
O1—C1—C12—S11 | −2.53 (19) | C31—C32—C33—C34 | −0.3 (2) |
C2—C1—C12—S11 | 178.07 (10) | C32—C33—C34—C35 | −1.4 (2) |
C15—S11—C12—C13 | −0.13 (12) | C32—C33—C34—C37 | 176.37 (14) |
C15—S11—C12—C1 | −179.87 (11) | C33—C34—C35—C36 | 1.1 (2) |
C1—C12—C13—C14 | 179.89 (14) | C37—C34—C35—C36 | −176.71 (15) |
S11—C12—C13—C14 | 0.20 (17) | C34—C35—C36—C31 | 0.9 (2) |
C12—C13—C14—C15 | −0.18 (19) | C32—C31—C36—C35 | −2.5 (2) |
C13—C14—C15—S11 | 0.07 (17) | C3—C31—C36—C35 | 174.48 (14) |
C13—C14—C15—Cl15 | 179.21 (11) | C33—C34—C37—C38 | −97.5 (2) |
C12—S11—C15—C14 | 0.03 (12) | C35—C34—C37—C38 | 80.2 (2) |
C15H13BrOS | Z = 2 |
Mr = 321.21 | F(000) = 324 |
Triclinic, P1 | Dx = 1.589 Mg m−3 |
a = 5.9745 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.6636 (7) Å | Cell parameters from 4444 reflections |
c = 14.3039 (12) Å | θ = 3.4–32.8° |
α = 74.731 (7)° | µ = 3.20 mm−1 |
β = 88.146 (7)° | T = 173 K |
γ = 70.334 (8)° | Needle, colourless |
V = 671.29 (11) Å3 | 0.45 × 0.22 × 0.16 mm |
Agilent Eos Gemini diffractometer | 3089 reflections with I > 2σ(I) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.042 |
ω scans | θmax = 30.0°, θmin = 3.4° |
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012) | h = −6→8 |
Tmin = 0.326, Tmax = 0.599 | k = −12→12 |
6997 measured reflections | l = −20→17 |
3915 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.041 | w = 1/[σ2(Fo2) + (0.0284P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.090 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.59 e Å−3 |
3915 reflections | Δρmin = −0.63 e Å−3 |
165 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0046 (13) |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.6905 (4) | 0.2599 (3) | 0.54692 (19) | 0.0229 (5) | |
O1 | 0.9055 (3) | 0.2306 (3) | 0.54185 (14) | 0.0324 (4) | |
C2 | 0.5458 (4) | 0.2270 (3) | 0.47838 (18) | 0.0243 (5) | |
H2 | 0.3775 | 0.2652 | 0.4813 | 0.029* | |
C3 | 0.6430 (4) | 0.1457 (3) | 0.41244 (19) | 0.0245 (5) | |
H3 | 0.8121 | 0.1024 | 0.4149 | 0.029* | |
S11 | 0.73910 (10) | 0.36381 (8) | 0.70722 (5) | 0.02472 (15) | |
C12 | 0.5672 (4) | 0.3334 (3) | 0.62337 (18) | 0.0201 (5) | |
C13 | 0.3321 (4) | 0.3826 (3) | 0.64308 (19) | 0.0237 (5) | |
H13 | 0.2105 | 0.3752 | 0.6051 | 0.028* | |
C14 | 0.2892 (4) | 0.4455 (3) | 0.72571 (19) | 0.0257 (5) | |
H14 | 0.1361 | 0.4855 | 0.7496 | 0.031* | |
C15 | 0.4928 (4) | 0.4419 (3) | 0.76705 (18) | 0.0226 (5) | |
Br15 | 0.52162 (5) | 0.51602 (4) | 0.87603 (2) | 0.03340 (11) | |
C31 | 0.5186 (4) | 0.1155 (3) | 0.33650 (18) | 0.0228 (5) | |
C32 | 0.6500 (4) | 0.0257 (3) | 0.27336 (19) | 0.0260 (5) | |
H32 | 0.8183 | −0.0232 | 0.2839 | 0.031* | |
C33 | 0.5396 (5) | 0.0066 (3) | 0.1957 (2) | 0.0287 (6) | |
H33 | 0.6335 | −0.0542 | 0.1535 | 0.034* | |
C34 | 0.2949 (5) | 0.0745 (3) | 0.17838 (19) | 0.0269 (5) | |
C35 | 0.1633 (4) | 0.1596 (4) | 0.2431 (2) | 0.0294 (6) | |
H35 | −0.0053 | 0.2054 | 0.2335 | 0.035* | |
C36 | 0.2716 (4) | 0.1791 (3) | 0.32083 (19) | 0.0270 (5) | |
H36 | 0.1767 | 0.2365 | 0.3641 | 0.032* | |
C37 | 0.1733 (5) | 0.0654 (4) | 0.0903 (2) | 0.0368 (7) | |
H37A | 0.2707 | −0.0368 | 0.0703 | 0.044* | |
H37B | 0.0168 | 0.0536 | 0.1074 | 0.044* | |
C38 | 0.1372 (6) | 0.2197 (4) | 0.0072 (2) | 0.0462 (8) | |
H38A | 0.0542 | 0.2101 | −0.0479 | 0.069* | |
H38B | 0.2921 | 0.2290 | −0.0119 | 0.069* | |
H38C | 0.0414 | 0.3212 | 0.0268 | 0.069* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0230 (11) | 0.0202 (12) | 0.0231 (13) | −0.0046 (10) | 0.0008 (10) | −0.0051 (10) |
O1 | 0.0224 (9) | 0.0440 (12) | 0.0324 (11) | −0.0077 (8) | 0.0034 (8) | −0.0176 (10) |
C2 | 0.0209 (11) | 0.0284 (14) | 0.0249 (13) | −0.0083 (10) | 0.0031 (10) | −0.0096 (11) |
C3 | 0.0253 (12) | 0.0258 (13) | 0.0232 (13) | −0.0095 (10) | 0.0025 (10) | −0.0070 (11) |
S11 | 0.0193 (3) | 0.0315 (4) | 0.0256 (3) | −0.0089 (3) | 0.0004 (2) | −0.0111 (3) |
C12 | 0.0205 (10) | 0.0213 (12) | 0.0208 (12) | −0.0090 (9) | 0.0006 (9) | −0.0071 (10) |
C13 | 0.0216 (11) | 0.0272 (13) | 0.0261 (13) | −0.0106 (10) | 0.0011 (10) | −0.0107 (11) |
C14 | 0.0216 (11) | 0.0295 (14) | 0.0293 (14) | −0.0096 (10) | 0.0062 (10) | −0.0131 (12) |
C15 | 0.0275 (11) | 0.0215 (12) | 0.0207 (12) | −0.0095 (10) | 0.0039 (10) | −0.0073 (10) |
Br15 | 0.04273 (18) | 0.03937 (19) | 0.02491 (16) | −0.01791 (13) | 0.00177 (11) | −0.01472 (13) |
C31 | 0.0266 (12) | 0.0234 (13) | 0.0202 (12) | −0.0100 (10) | 0.0046 (10) | −0.0074 (10) |
C32 | 0.0278 (12) | 0.0226 (13) | 0.0275 (14) | −0.0060 (10) | 0.0044 (10) | −0.0105 (11) |
C33 | 0.0382 (14) | 0.0253 (14) | 0.0280 (15) | −0.0127 (11) | 0.0095 (11) | −0.0146 (12) |
C34 | 0.0360 (13) | 0.0277 (14) | 0.0248 (13) | −0.0197 (11) | 0.0042 (11) | −0.0088 (11) |
C35 | 0.0262 (12) | 0.0346 (15) | 0.0329 (15) | −0.0138 (11) | 0.0044 (11) | −0.0140 (13) |
C36 | 0.0271 (12) | 0.0309 (14) | 0.0271 (14) | −0.0113 (11) | 0.0070 (10) | −0.0136 (12) |
C37 | 0.0421 (15) | 0.0477 (19) | 0.0337 (16) | −0.0244 (14) | 0.0052 (13) | −0.0212 (15) |
C38 | 0.0543 (19) | 0.048 (2) | 0.0350 (18) | −0.0118 (16) | −0.0089 (15) | −0.0155 (16) |
C1—O1 | 1.226 (3) | C31—C32 | 1.397 (3) |
C1—C12 | 1.464 (3) | C32—C33 | 1.383 (3) |
C1—C2 | 1.468 (3) | C32—H32 | 0.9500 |
C2—C3 | 1.328 (3) | C33—C34 | 1.383 (4) |
C2—H2 | 0.9500 | C33—H33 | 0.9500 |
C3—C31 | 1.461 (3) | C34—C35 | 1.394 (3) |
C3—H3 | 0.9500 | C34—C37 | 1.507 (3) |
S11—C15 | 1.705 (2) | C35—C36 | 1.379 (3) |
S11—C12 | 1.729 (2) | C35—H35 | 0.9500 |
C12—C13 | 1.367 (3) | C36—H36 | 0.9500 |
C13—C14 | 1.409 (3) | C37—C38 | 1.494 (5) |
C13—H13 | 0.9500 | C37—H37A | 0.9900 |
C14—C15 | 1.358 (3) | C37—H37B | 0.9900 |
C14—H14 | 0.9500 | C38—H38A | 0.9800 |
C15—Br15 | 1.868 (2) | C38—H38B | 0.9800 |
C31—C36 | 1.393 (3) | C38—H38C | 0.9800 |
O1—C1—C12 | 119.6 (2) | C33—C32—H32 | 119.4 |
O1—C1—C2 | 123.1 (2) | C31—C32—H32 | 119.4 |
C12—C1—C2 | 117.3 (2) | C34—C33—C32 | 121.2 (2) |
C3—C2—C1 | 122.0 (2) | C34—C33—H33 | 119.4 |
C3—C2—H2 | 119.0 | C32—C33—H33 | 119.4 |
C1—C2—H2 | 119.0 | C33—C34—C35 | 117.6 (2) |
C2—C3—C31 | 127.2 (2) | C33—C34—C37 | 121.8 (2) |
C2—C3—H3 | 116.4 | C35—C34—C37 | 120.5 (2) |
C31—C3—H3 | 116.4 | C36—C35—C34 | 121.7 (2) |
C15—S11—C12 | 90.81 (11) | C36—C35—H35 | 119.2 |
C13—C12—C1 | 131.3 (2) | C34—C35—H35 | 119.2 |
C13—C12—S11 | 111.33 (17) | C35—C36—C31 | 120.7 (2) |
C1—C12—S11 | 117.35 (16) | C35—C36—H36 | 119.6 |
C12—C13—C14 | 112.9 (2) | C31—C36—H36 | 119.6 |
C12—C13—H13 | 123.6 | C38—C37—C34 | 112.1 (2) |
C14—C13—H13 | 123.6 | C38—C37—H37A | 109.2 |
C15—C14—C13 | 111.9 (2) | C34—C37—H37A | 109.2 |
C15—C14—H14 | 124.1 | C38—C37—H37B | 109.2 |
C13—C14—H14 | 124.1 | C34—C37—H37B | 109.2 |
C14—C15—S11 | 113.11 (17) | H37A—C37—H37B | 107.9 |
C14—C15—Br15 | 126.95 (18) | C37—C38—H38A | 109.5 |
S11—C15—Br15 | 119.93 (13) | C37—C38—H38B | 109.5 |
C36—C31—C32 | 117.6 (2) | H38A—C38—H38B | 109.5 |
C36—C31—C3 | 122.8 (2) | C37—C38—H38C | 109.5 |
C32—C31—C3 | 119.5 (2) | H38A—C38—H38C | 109.5 |
C33—C32—C31 | 121.2 (2) | H38B—C38—H38C | 109.5 |
O1—C1—C2—C3 | 7.6 (4) | C12—S11—C15—Br15 | −178.81 (16) |
C12—C1—C2—C3 | −173.3 (3) | C2—C3—C31—C36 | 3.5 (4) |
C1—C2—C3—C31 | −175.6 (2) | C2—C3—C31—C32 | −179.5 (3) |
O1—C1—C12—C13 | 177.6 (3) | C36—C31—C32—C33 | 2.6 (4) |
C2—C1—C12—C13 | −1.5 (4) | C3—C31—C32—C33 | −174.6 (2) |
O1—C1—C12—S11 | −3.5 (3) | C31—C32—C33—C34 | −0.6 (4) |
C2—C1—C12—S11 | 177.34 (18) | C32—C33—C34—C35 | −1.3 (4) |
C15—S11—C12—C13 | 0.0 (2) | C32—C33—C34—C37 | 175.7 (2) |
C15—S11—C12—C1 | −179.1 (2) | C33—C34—C35—C36 | 1.2 (4) |
C1—C12—C13—C14 | 179.0 (3) | C37—C34—C35—C36 | −175.8 (3) |
S11—C12—C13—C14 | 0.1 (3) | C34—C35—C36—C31 | 0.8 (4) |
C12—C13—C14—C15 | −0.2 (3) | C32—C31—C36—C35 | −2.7 (4) |
C13—C14—C15—S11 | 0.2 (3) | C3—C31—C36—C35 | 174.4 (2) |
C13—C14—C15—Br15 | 178.79 (19) | C33—C34—C37—C38 | −92.6 (3) |
C12—S11—C15—C14 | −0.1 (2) | C35—C34—C37—C38 | 84.4 (3) |
C15H13ClO2S | F(000) = 608 |
Mr = 292.76 | Dx = 1.440 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.3577 (6) Å | Cell parameters from 4472 reflections |
b = 7.4518 (4) Å | θ = 3.6–32.8° |
c = 11.0892 (4) Å | µ = 0.43 mm−1 |
β = 92.260 (3)° | T = 173 K |
V = 1350.66 (10) Å3 | Needle, colourless |
Z = 4 | 0.50 × 0.28 × 0.17 mm |
Agilent Eos Gemini diffractometer | 3102 reflections with I > 2σ(I) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.038 |
ω scans | θmax = 30.0°, θmin = 3.6° |
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012) | h = −23→12 |
Tmin = 0.789, Tmax = 0.929 | k = −9→10 |
7925 measured reflections | l = −15→15 |
3933 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.111 | w = 1/[σ2(Fo2) + (0.0511P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
3933 reflections | Δρmax = 0.28 e Å−3 |
173 parameters | Δρmin = −0.39 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.48158 (9) | 0.8068 (2) | 0.36984 (12) | 0.0216 (3) | |
O1 | 0.46622 (7) | 0.8563 (2) | 0.26556 (9) | 0.0323 (3) | |
C2 | 0.42015 (9) | 0.7307 (2) | 0.44768 (12) | 0.0224 (3) | |
H2 | 0.4360 | 0.6950 | 0.5275 | 0.027* | |
C3 | 0.34250 (9) | 0.7104 (2) | 0.40898 (12) | 0.0203 (3) | |
H3 | 0.3296 | 0.7470 | 0.3284 | 0.024* | |
S11 | 0.63794 (2) | 0.91918 (6) | 0.33294 (3) | 0.02406 (12) | |
C12 | 0.56528 (9) | 0.8246 (2) | 0.42167 (12) | 0.0200 (3) | |
C13 | 0.59796 (9) | 0.7742 (2) | 0.53208 (13) | 0.0219 (3) | |
H313 | 0.5670 | 0.7205 | 0.5932 | 0.026* | |
C14 | 0.68245 (9) | 0.8104 (2) | 0.54546 (13) | 0.0233 (3) | |
H14 | 0.7151 | 0.7840 | 0.6160 | 0.028* | |
C15 | 0.71118 (9) | 0.8880 (2) | 0.44464 (13) | 0.0217 (3) | |
Cl15 | 0.81004 (2) | 0.95089 (6) | 0.42162 (4) | 0.03018 (12) | |
C31 | 0.27552 (9) | 0.6388 (2) | 0.47614 (12) | 0.0189 (3) | |
C32 | 0.19780 (9) | 0.6176 (2) | 0.41992 (13) | 0.0229 (3) | |
H32 | 0.1900 | 0.6488 | 0.3372 | 0.027* | |
C33 | 0.13266 (9) | 0.5529 (2) | 0.48145 (14) | 0.0245 (3) | |
H33 | 0.0807 | 0.5394 | 0.4412 | 0.029* | |
C34 | 0.14307 (9) | 0.5074 (2) | 0.60284 (13) | 0.0215 (3) | |
C35 | 0.21977 (9) | 0.5257 (2) | 0.66077 (13) | 0.0220 (3) | |
H35 | 0.2274 | 0.4940 | 0.7434 | 0.026* | |
C36 | 0.28472 (9) | 0.5902 (2) | 0.59763 (13) | 0.0212 (3) | |
H36 | 0.3369 | 0.6017 | 0.6377 | 0.025* | |
O34 | 0.07523 (7) | 0.44649 (17) | 0.65798 (10) | 0.0274 (3) | |
C37 | 0.08278 (10) | 0.4097 (3) | 0.78481 (14) | 0.0304 (4) | |
H37A | 0.1087 | 0.5125 | 0.8281 | 0.036* | |
H37B | 0.1170 | 0.3019 | 0.7999 | 0.036* | |
C38 | −0.00225 (12) | 0.3790 (3) | 0.82785 (18) | 0.0427 (5) | |
H38A | −0.0281 | 0.2806 | 0.7817 | 0.064* | |
H38B | −0.0347 | 0.4886 | 0.8161 | 0.064* | |
H38C | 0.0007 | 0.3476 | 0.9137 | 0.064* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0198 (7) | 0.0260 (8) | 0.0190 (6) | 0.0008 (7) | 0.0008 (5) | −0.0012 (6) |
O1 | 0.0234 (6) | 0.0528 (9) | 0.0206 (5) | −0.0050 (6) | −0.0009 (4) | 0.0065 (5) |
C2 | 0.0215 (7) | 0.0261 (8) | 0.0196 (6) | −0.0009 (7) | 0.0016 (5) | 0.0003 (6) |
C3 | 0.0214 (7) | 0.0216 (8) | 0.0180 (6) | 0.0004 (6) | 0.0018 (5) | −0.0024 (5) |
S11 | 0.02107 (19) | 0.0335 (2) | 0.01778 (18) | −0.00399 (17) | 0.00259 (14) | 0.00242 (15) |
C12 | 0.0185 (7) | 0.0230 (8) | 0.0185 (6) | −0.0016 (6) | 0.0033 (5) | −0.0008 (5) |
C13 | 0.0212 (7) | 0.0255 (8) | 0.0192 (6) | −0.0018 (7) | 0.0026 (5) | 0.0020 (6) |
C14 | 0.0216 (7) | 0.0250 (8) | 0.0231 (7) | −0.0011 (7) | −0.0022 (5) | 0.0013 (6) |
C15 | 0.0185 (7) | 0.0209 (8) | 0.0258 (7) | −0.0007 (6) | 0.0014 (6) | −0.0041 (6) |
Cl15 | 0.01899 (19) | 0.0340 (3) | 0.0378 (2) | −0.00428 (17) | 0.00436 (16) | −0.00219 (17) |
C31 | 0.0175 (6) | 0.0190 (8) | 0.0202 (6) | 0.0008 (6) | 0.0009 (5) | −0.0031 (6) |
C32 | 0.0214 (7) | 0.0276 (9) | 0.0195 (7) | 0.0005 (7) | −0.0018 (5) | −0.0001 (6) |
C33 | 0.0176 (7) | 0.0297 (9) | 0.0260 (7) | −0.0006 (7) | −0.0040 (6) | −0.0026 (6) |
C34 | 0.0172 (7) | 0.0217 (8) | 0.0257 (7) | −0.0007 (6) | 0.0032 (6) | −0.0024 (6) |
C35 | 0.0202 (7) | 0.0269 (8) | 0.0188 (7) | 0.0010 (7) | 0.0008 (5) | −0.0003 (6) |
C36 | 0.0174 (7) | 0.0247 (8) | 0.0213 (7) | −0.0003 (6) | −0.0021 (5) | −0.0021 (6) |
O34 | 0.0190 (5) | 0.0351 (7) | 0.0283 (6) | −0.0048 (5) | 0.0039 (4) | 0.0023 (5) |
C37 | 0.0279 (8) | 0.0358 (10) | 0.0279 (8) | −0.0025 (8) | 0.0072 (7) | 0.0027 (7) |
C38 | 0.0357 (10) | 0.0494 (13) | 0.0440 (10) | −0.0071 (10) | 0.0159 (8) | 0.0049 (9) |
C1—O1 | 1.2302 (17) | C32—C33 | 1.375 (2) |
C1—C2 | 1.465 (2) | C32—H32 | 0.9500 |
C1—C12 | 1.4698 (19) | C33—C34 | 1.392 (2) |
C2—C3 | 1.333 (2) | C33—H33 | 0.9500 |
C2—H2 | 0.9500 | C34—O34 | 1.3654 (19) |
C3—C31 | 1.451 (2) | C34—C35 | 1.394 (2) |
C3—H3 | 0.9500 | C35—C36 | 1.381 (2) |
S11—C15 | 1.7049 (15) | C35—H35 | 0.9500 |
S11—C12 | 1.7233 (15) | C36—H36 | 0.9500 |
C12—C13 | 1.369 (2) | O34—C37 | 1.4335 (19) |
C13—C14 | 1.410 (2) | C37—C38 | 1.506 (2) |
C13—H313 | 0.9500 | C37—H37A | 0.9900 |
C14—C15 | 1.359 (2) | C37—H37B | 0.9900 |
C14—H14 | 0.9500 | C38—H38A | 0.9800 |
C15—Cl15 | 1.7125 (15) | C38—H38B | 0.9800 |
C31—C36 | 1.398 (2) | C38—H38C | 0.9800 |
C31—C32 | 1.4027 (19) | ||
O1—C1—C2 | 123.41 (13) | C31—C32—H32 | 119.2 |
O1—C1—C12 | 119.55 (13) | C32—C33—C34 | 119.86 (14) |
C2—C1—C12 | 117.04 (12) | C32—C33—H33 | 120.1 |
C3—C2—C1 | 121.42 (13) | C34—C33—H33 | 120.1 |
C3—C2—H2 | 119.3 | O34—C34—C33 | 116.33 (13) |
C1—C2—H2 | 119.3 | O34—C34—C35 | 123.98 (13) |
C2—C3—C31 | 127.28 (13) | C33—C34—C35 | 119.69 (14) |
C2—C3—H3 | 116.4 | C36—C35—C34 | 119.79 (14) |
C31—C3—H3 | 116.4 | C36—C35—H35 | 120.1 |
C15—S11—C12 | 90.58 (7) | C34—C35—H35 | 120.1 |
C13—C12—C1 | 130.54 (14) | C35—C36—C31 | 121.54 (14) |
C13—C12—S11 | 111.66 (11) | C35—C36—H36 | 119.2 |
C1—C12—S11 | 117.79 (10) | C31—C36—H36 | 119.2 |
C12—C13—C14 | 112.83 (13) | C34—O34—C37 | 117.57 (12) |
C12—C13—H313 | 123.6 | O34—C37—C38 | 107.17 (14) |
C14—C13—H313 | 123.6 | O34—C37—H37A | 110.3 |
C15—C14—C13 | 111.36 (13) | C38—C37—H37A | 110.3 |
C15—C14—H14 | 124.3 | O34—C37—H37B | 110.3 |
C13—C14—H14 | 124.3 | C38—C37—H37B | 110.3 |
C14—C15—S11 | 113.57 (11) | H37A—C37—H37B | 108.5 |
C14—C15—Cl15 | 126.75 (12) | C37—C38—H38A | 109.5 |
S11—C15—Cl15 | 119.67 (9) | C37—C38—H38B | 109.5 |
C36—C31—C32 | 117.42 (13) | H38A—C38—H38B | 109.5 |
C36—C31—C3 | 122.39 (13) | C37—C38—H38C | 109.5 |
C32—C31—C3 | 120.20 (12) | H38A—C38—H38C | 109.5 |
C33—C32—C31 | 121.70 (13) | H38B—C38—H38C | 109.5 |
C33—C32—H32 | 119.2 | ||
O1—C1—C2—C3 | 0.0 (3) | C2—C3—C31—C36 | 4.0 (3) |
C12—C1—C2—C3 | 179.55 (15) | C2—C3—C31—C32 | −176.64 (16) |
C1—C2—C3—C31 | −179.46 (15) | C36—C31—C32—C33 | 0.5 (2) |
O1—C1—C12—C13 | −177.31 (17) | C3—C31—C32—C33 | −178.92 (15) |
C2—C1—C12—C13 | 3.1 (3) | C31—C32—C33—C34 | 0.2 (3) |
O1—C1—C12—S11 | 1.2 (2) | C32—C33—C34—O34 | 179.12 (15) |
C2—C1—C12—S11 | −178.36 (12) | C32—C33—C34—C35 | −0.7 (2) |
C15—S11—C12—C13 | 0.49 (13) | O34—C34—C35—C36 | −179.38 (15) |
C15—S11—C12—C1 | −178.32 (13) | C33—C34—C35—C36 | 0.5 (2) |
C1—C12—C13—C14 | 178.12 (16) | C34—C35—C36—C31 | 0.3 (2) |
S11—C12—C13—C14 | −0.50 (18) | C32—C31—C36—C35 | −0.8 (2) |
C12—C13—C14—C15 | 0.2 (2) | C3—C31—C36—C35 | 178.63 (15) |
C13—C14—C15—S11 | 0.15 (19) | C33—C34—O34—C37 | −175.99 (15) |
C13—C14—C15—Cl15 | −179.02 (12) | C35—C34—O34—C37 | 3.9 (2) |
C12—S11—C15—C14 | −0.37 (14) | C34—O34—C37—C38 | 169.60 (16) |
C12—S11—C15—Cl15 | 178.87 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
C36—H36···O1i | 0.95 | 2.52 | 3.4649 (18) | 173 |
Symmetry code: (i) x, −y+3/2, z+1/2. |
C15H13BrO2S | F(000) = 680 |
Mr = 337.21 | Dx = 1.617 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.5498 (7) Å | Cell parameters from 4590 reflections |
b = 7.5069 (4) Å | θ = 3.3–32.8° |
c = 11.1574 (5) Å | µ = 3.11 mm−1 |
β = 92.618 (4)° | T = 173 K |
V = 1384.72 (11) Å3 | Needle, colourless |
Z = 4 | 0.58 × 0.32 × 0.29 mm |
Agilent Eos Gemini diffractometer | 3189 reflections with I > 2σ(I) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.037 |
ω scans | θmax = 30.0°, θmin = 3.3° |
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012) | h = −23→23 |
Tmin = 0.261, Tmax = 0.405 | k = −10→7 |
8866 measured reflections | l = −15→10 |
4040 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.038 | w = 1/[σ2(Fo2) + (0.027P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.078 | (Δ/σ)max = 0.002 |
S = 1.03 | Δρmax = 0.54 e Å−3 |
4040 reflections | Δρmin = −0.43 e Å−3 |
174 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0142 (6) |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.47683 (13) | 0.8021 (3) | 0.37094 (19) | 0.0214 (5) | |
O1 | 0.46163 (10) | 0.8474 (2) | 0.26618 (14) | 0.0325 (4) | |
C2 | 0.41612 (13) | 0.7286 (3) | 0.44882 (19) | 0.0219 (5) | |
H2 | 0.4316 | 0.6977 | 0.5292 | 0.026* | |
C3 | 0.33987 (13) | 0.7040 (3) | 0.40968 (19) | 0.0198 (4) | |
H3 | 0.3274 | 0.7351 | 0.3284 | 0.024* | |
S11 | 0.63142 (3) | 0.91205 (8) | 0.33350 (5) | 0.02358 (14) | |
C12 | 0.55978 (13) | 0.8208 (3) | 0.42271 (19) | 0.0197 (4) | |
C13 | 0.59275 (14) | 0.7744 (3) | 0.5328 (2) | 0.0237 (5) | |
H313 | 0.5625 | 0.7231 | 0.5943 | 0.028* | |
C14 | 0.67601 (13) | 0.8103 (3) | 0.5458 (2) | 0.0227 (5) | |
H14 | 0.7083 | 0.7865 | 0.6165 | 0.027* | |
C15 | 0.70441 (13) | 0.8830 (3) | 0.44500 (19) | 0.0197 (4) | |
Br15 | 0.81072 (2) | 0.95080 (3) | 0.41891 (2) | 0.02718 (9) | |
C31 | 0.27341 (12) | 0.6353 (3) | 0.47671 (18) | 0.0174 (4) | |
C32 | 0.19658 (13) | 0.6155 (3) | 0.42083 (19) | 0.0220 (5) | |
H32 | 0.1888 | 0.6455 | 0.3384 | 0.026* | |
C33 | 0.13207 (14) | 0.5537 (3) | 0.4821 (2) | 0.0228 (5) | |
H33 | 0.0806 | 0.5404 | 0.4420 | 0.027* | |
C34 | 0.14246 (13) | 0.5107 (3) | 0.6032 (2) | 0.0201 (4) | |
C35 | 0.21844 (14) | 0.5284 (3) | 0.6608 (2) | 0.0214 (5) | |
H35 | 0.2259 | 0.4987 | 0.7433 | 0.026* | |
C36 | 0.28283 (13) | 0.5889 (3) | 0.59792 (19) | 0.0195 (4) | |
H36 | 0.3346 | 0.5993 | 0.6378 | 0.023* | |
O34 | 0.07528 (9) | 0.4517 (2) | 0.65781 (15) | 0.0260 (4) | |
C37 | 0.08296 (15) | 0.4163 (3) | 0.7841 (2) | 0.0294 (5) | |
H37A | 0.1074 | 0.5198 | 0.8270 | 0.035* | |
H37B | 0.1180 | 0.3111 | 0.7997 | 0.035* | |
C38 | −0.00045 (16) | 0.3818 (4) | 0.8261 (3) | 0.0414 (7) | |
H38A | −0.0259 | 0.2861 | 0.7780 | 0.062* | |
H38B | −0.0330 | 0.4904 | 0.8172 | 0.062* | |
H38C | 0.0031 | 0.3462 | 0.9107 | 0.062* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0219 (11) | 0.0234 (11) | 0.0191 (11) | −0.0007 (9) | 0.0017 (8) | −0.0020 (9) |
O1 | 0.0238 (9) | 0.0546 (11) | 0.0189 (8) | −0.0044 (8) | −0.0014 (7) | 0.0074 (8) |
C2 | 0.0217 (11) | 0.0276 (12) | 0.0164 (11) | −0.0005 (9) | 0.0019 (8) | 0.0022 (9) |
C3 | 0.0230 (11) | 0.0200 (10) | 0.0164 (10) | 0.0005 (9) | 0.0033 (8) | −0.0013 (9) |
S11 | 0.0220 (3) | 0.0332 (3) | 0.0157 (3) | −0.0040 (2) | 0.0026 (2) | 0.0027 (2) |
C12 | 0.0191 (11) | 0.0228 (11) | 0.0173 (10) | −0.0009 (9) | 0.0041 (8) | −0.0003 (9) |
C13 | 0.0237 (12) | 0.0246 (11) | 0.0228 (12) | −0.0026 (10) | 0.0019 (9) | 0.0039 (10) |
C14 | 0.0225 (11) | 0.0236 (11) | 0.0216 (11) | −0.0020 (9) | −0.0033 (9) | 0.0020 (9) |
C15 | 0.0169 (10) | 0.0189 (10) | 0.0233 (11) | 0.0011 (9) | 0.0015 (8) | −0.0016 (9) |
Br15 | 0.01970 (13) | 0.02854 (14) | 0.03363 (15) | −0.00331 (9) | 0.00473 (9) | −0.00198 (10) |
C31 | 0.0179 (10) | 0.0166 (10) | 0.0176 (10) | 0.0017 (8) | 0.0012 (8) | −0.0029 (8) |
C32 | 0.0235 (12) | 0.0252 (11) | 0.0170 (11) | 0.0002 (10) | −0.0024 (9) | −0.0011 (9) |
C33 | 0.0162 (11) | 0.0269 (12) | 0.0250 (12) | −0.0015 (9) | −0.0024 (9) | −0.0018 (10) |
C34 | 0.0177 (11) | 0.0195 (10) | 0.0232 (11) | 0.0006 (9) | 0.0030 (9) | −0.0028 (9) |
C35 | 0.0224 (11) | 0.0247 (11) | 0.0170 (11) | 0.0004 (9) | 0.0006 (8) | 0.0014 (9) |
C36 | 0.0162 (10) | 0.0229 (11) | 0.0194 (11) | −0.0002 (9) | −0.0009 (8) | −0.0013 (9) |
O34 | 0.0185 (8) | 0.0340 (9) | 0.0259 (9) | −0.0048 (7) | 0.0041 (6) | 0.0010 (7) |
C37 | 0.0293 (13) | 0.0333 (13) | 0.0261 (12) | −0.0032 (11) | 0.0074 (10) | 0.0028 (11) |
C38 | 0.0353 (15) | 0.0489 (16) | 0.0414 (16) | −0.0083 (13) | 0.0154 (12) | 0.0042 (14) |
C1—O1 | 1.232 (3) | C32—C33 | 1.375 (3) |
C1—C2 | 1.466 (3) | C32—H32 | 0.9500 |
C1—C12 | 1.472 (3) | C33—C34 | 1.392 (3) |
C2—C3 | 1.329 (3) | C33—H33 | 0.9500 |
C2—H2 | 0.9500 | C34—O34 | 1.366 (3) |
C3—C31 | 1.453 (3) | C34—C35 | 1.392 (3) |
C3—H3 | 0.9500 | C35—C36 | 1.379 (3) |
S11—C15 | 1.708 (2) | C35—H35 | 0.9500 |
S11—C12 | 1.724 (2) | C36—H36 | 0.9500 |
C12—C13 | 1.366 (3) | O34—C37 | 1.434 (3) |
C13—C14 | 1.405 (3) | C37—C38 | 1.501 (3) |
C13—H313 | 0.9500 | C37—H37A | 0.9900 |
C14—C15 | 1.353 (3) | C37—H37B | 0.9900 |
C14—H14 | 0.9500 | C38—H38A | 0.9800 |
C15—Br15 | 1.867 (2) | C38—H38B | 0.9800 |
C31—C36 | 1.398 (3) | C38—H38C | 0.9800 |
C31—C32 | 1.398 (3) | ||
O1—C1—C2 | 123.4 (2) | C31—C32—H32 | 119.2 |
O1—C1—C12 | 119.5 (2) | C32—C33—C34 | 119.8 (2) |
C2—C1—C12 | 117.09 (19) | C32—C33—H33 | 120.1 |
C3—C2—C1 | 121.6 (2) | C34—C33—H33 | 120.1 |
C3—C2—H2 | 119.2 | O34—C34—C33 | 116.2 (2) |
C1—C2—H2 | 119.2 | O34—C34—C35 | 124.2 (2) |
C2—C3—C31 | 127.6 (2) | C33—C34—C35 | 119.7 (2) |
C2—C3—H3 | 116.2 | C36—C35—C34 | 120.0 (2) |
C31—C3—H3 | 116.2 | C36—C35—H35 | 120.0 |
C15—S11—C12 | 90.62 (10) | C34—C35—H35 | 120.0 |
C13—C12—C1 | 131.0 (2) | C35—C36—C31 | 121.3 (2) |
C13—C12—S11 | 111.31 (17) | C35—C36—H36 | 119.4 |
C1—C12—S11 | 117.70 (16) | C31—C36—H36 | 119.4 |
C12—C13—C14 | 113.2 (2) | C34—O34—C37 | 117.45 (18) |
C12—C13—H313 | 123.4 | O34—C37—C38 | 107.3 (2) |
C14—C13—H313 | 123.4 | O34—C37—H37A | 110.2 |
C15—C14—C13 | 111.6 (2) | C38—C37—H37A | 110.2 |
C15—C14—H14 | 124.2 | O34—C37—H37B | 110.2 |
C13—C14—H14 | 124.2 | C38—C37—H37B | 110.2 |
C14—C15—S11 | 113.31 (16) | H37A—C37—H37B | 108.5 |
C14—C15—Br15 | 127.23 (17) | C37—C38—H38A | 109.5 |
S11—C15—Br15 | 119.46 (12) | C37—C38—H38B | 109.5 |
C36—C31—C32 | 117.6 (2) | H38A—C38—H38B | 109.5 |
C36—C31—C3 | 122.2 (2) | C37—C38—H38C | 109.5 |
C32—C31—C3 | 120.17 (19) | H38A—C38—H38C | 109.5 |
C33—C32—C31 | 121.7 (2) | H38B—C38—H38C | 109.5 |
C33—C32—H32 | 119.2 | ||
O1—C1—C2—C3 | 0.8 (4) | C2—C3—C31—C36 | 1.7 (4) |
C12—C1—C2—C3 | −178.9 (2) | C2—C3—C31—C32 | −179.1 (2) |
C1—C2—C3—C31 | −179.0 (2) | C36—C31—C32—C33 | 0.4 (3) |
O1—C1—C12—C13 | −176.9 (2) | C3—C31—C32—C33 | −178.9 (2) |
C2—C1—C12—C13 | 2.9 (4) | C31—C32—C33—C34 | 0.6 (3) |
O1—C1—C12—S11 | 1.8 (3) | C32—C33—C34—O34 | 179.5 (2) |
C2—C1—C12—S11 | −178.48 (16) | C32—C33—C34—C35 | −0.9 (3) |
C15—S11—C12—C13 | 0.85 (18) | O34—C34—C35—C36 | 179.9 (2) |
C15—S11—C12—C1 | −178.06 (17) | C33—C34—C35—C36 | 0.3 (3) |
C1—C12—C13—C14 | 178.1 (2) | C34—C35—C36—C31 | 0.6 (3) |
S11—C12—C13—C14 | −0.6 (3) | C32—C31—C36—C35 | −1.0 (3) |
C12—C13—C14—C15 | −0.1 (3) | C3—C31—C36—C35 | 178.3 (2) |
C13—C14—C15—S11 | 0.8 (3) | C33—C34—O34—C37 | −176.45 (19) |
C13—C14—C15—Br15 | −179.32 (16) | C35—C34—O34—C37 | 4.0 (3) |
C12—S11—C15—C14 | −0.92 (18) | C34—O34—C37—C38 | 171.3 (2) |
C12—S11—C15—Br15 | 179.15 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
C36—H36···O1i | 0.95 | 2.52 | 3.464 (2) | 172 |
Symmetry code: (i) x, −y+3/2, z+1/2. |
C13H8BrClOS | Z = 2 |
Mr = 327.60 | F(000) = 324 |
Triclinic, P1 | Dx = 1.763 Mg m−3 |
a = 6.0152 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.5691 (12) Å | Cell parameters from 4058 reflections |
c = 13.1824 (9) Å | θ = 3.2–32.8° |
α = 75.25 (1)° | µ = 3.69 mm−1 |
β = 81.446 (8)° | T = 173 K |
γ = 70.281 (12)° | Needle, colourless |
V = 617.09 (14) Å3 | 0.41 × 0.20 × 0.18 mm |
Agilent Eos Gemini diffractometer | 2817 reflections with I > 2σ(I) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.026 |
ω scans | θmax = 30.0°, θmin = 3.2° |
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012) | h = −8→8 |
Tmin = 0.298, Tmax = 0.514 | k = −10→12 |
6674 measured reflections | l = −18→18 |
3599 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.100 | w = 1/[σ2(Fo2) + (0.0428P)2 + 0.3839P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3599 reflections | Δρmax = 1.43 e Å−3 |
154 parameters | Δρmin = −0.53 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.3079 (5) | 0.7031 (4) | 0.5481 (2) | 0.0219 (5) | |
O1 | 0.0931 (3) | 0.7382 (3) | 0.54196 (16) | 0.0316 (5) | |
C2 | 0.4552 (5) | 0.7932 (4) | 0.4740 (2) | 0.0233 (5) | |
H2 | 0.6221 | 0.7524 | 0.4781 | 0.028* | |
C3 | 0.3594 (5) | 0.9316 (4) | 0.4008 (2) | 0.0235 (5) | |
H3 | 0.1914 | 0.9731 | 0.4024 | 0.028* | |
S11 | 0.25627 (12) | 0.46020 (9) | 0.72271 (5) | 0.02442 (15) | |
C12 | 0.4287 (5) | 0.5637 (3) | 0.63199 (19) | 0.0209 (5) | |
C13 | 0.6614 (5) | 0.4996 (4) | 0.6548 (2) | 0.0230 (5) | |
H13 | 0.7821 | 0.5412 | 0.6141 | 0.028* | |
C14 | 0.7041 (5) | 0.3649 (4) | 0.7453 (2) | 0.0234 (5) | |
H14 | 0.8555 | 0.3055 | 0.7719 | 0.028* | |
C15 | 0.5014 (5) | 0.3316 (3) | 0.7890 (2) | 0.0228 (5) | |
Cl15 | 0.47267 (14) | 0.18017 (10) | 0.89894 (5) | 0.03458 (18) | |
C31 | 0.4883 (5) | 1.0255 (3) | 0.3183 (2) | 0.0215 (5) | |
C32 | 0.3621 (5) | 1.1691 (3) | 0.2476 (2) | 0.0236 (5) | |
H32 | 0.1943 | 1.2092 | 0.2575 | 0.028* | |
C33 | 0.4754 (5) | 1.2549 (4) | 0.1632 (2) | 0.0250 (5) | |
H33 | 0.3868 | 1.3509 | 0.1151 | 0.030* | |
C34 | 0.7182 (5) | 1.1974 (4) | 0.1513 (2) | 0.0247 (6) | |
Br34 | 0.87986 (6) | 1.31203 (4) | 0.03812 (2) | 0.03776 (12) | |
C35 | 0.8519 (5) | 1.0562 (4) | 0.2200 (2) | 0.0268 (6) | |
H35 | 1.0197 | 1.0177 | 0.2099 | 0.032* | |
C36 | 0.7356 (5) | 0.9725 (4) | 0.3037 (2) | 0.0255 (6) | |
H36 | 0.8255 | 0.8775 | 0.3519 | 0.031* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0238 (13) | 0.0213 (13) | 0.0195 (12) | −0.0059 (10) | −0.0023 (10) | −0.0036 (10) |
O1 | 0.0206 (10) | 0.0337 (12) | 0.0348 (11) | −0.0058 (9) | −0.0044 (8) | 0.0004 (9) |
C2 | 0.0221 (12) | 0.0250 (14) | 0.0221 (12) | −0.0089 (11) | −0.0016 (10) | −0.0022 (10) |
C3 | 0.0238 (13) | 0.0227 (14) | 0.0232 (12) | −0.0067 (11) | −0.0019 (10) | −0.0043 (10) |
S11 | 0.0193 (3) | 0.0278 (4) | 0.0247 (3) | −0.0094 (3) | 0.0003 (2) | −0.0015 (3) |
C12 | 0.0232 (13) | 0.0203 (13) | 0.0196 (11) | −0.0090 (10) | −0.0011 (10) | −0.0023 (9) |
C13 | 0.0223 (12) | 0.0255 (14) | 0.0226 (12) | −0.0108 (11) | −0.0015 (10) | −0.0031 (10) |
C14 | 0.0216 (12) | 0.0241 (14) | 0.0231 (12) | −0.0054 (11) | −0.0050 (10) | −0.0029 (10) |
C15 | 0.0259 (13) | 0.0216 (13) | 0.0206 (12) | −0.0084 (11) | −0.0022 (10) | −0.0025 (10) |
Cl15 | 0.0439 (4) | 0.0324 (4) | 0.0251 (3) | −0.0175 (3) | −0.0011 (3) | 0.0046 (3) |
C31 | 0.0228 (13) | 0.0213 (13) | 0.0206 (12) | −0.0070 (10) | −0.0027 (10) | −0.0043 (10) |
C32 | 0.0227 (13) | 0.0203 (14) | 0.0237 (12) | −0.0013 (10) | −0.0050 (10) | −0.0035 (10) |
C33 | 0.0279 (14) | 0.0201 (13) | 0.0242 (13) | −0.0045 (11) | −0.0082 (11) | −0.0005 (10) |
C34 | 0.0307 (14) | 0.0243 (14) | 0.0206 (12) | −0.0133 (12) | −0.0031 (10) | −0.0005 (10) |
Br34 | 0.03904 (19) | 0.0438 (2) | 0.02867 (17) | −0.02171 (15) | −0.00236 (12) | 0.00715 (13) |
C35 | 0.0224 (13) | 0.0262 (15) | 0.0302 (14) | −0.0080 (11) | −0.0060 (11) | −0.0005 (11) |
C36 | 0.0217 (13) | 0.0247 (14) | 0.0259 (13) | −0.0054 (11) | −0.0061 (10) | 0.0018 (10) |
C1—O1 | 1.234 (3) | C14—H14 | 0.9500 |
C1—C12 | 1.469 (4) | C15—Cl15 | 1.712 (3) |
C1—C2 | 1.469 (4) | C31—C32 | 1.398 (4) |
C2—C3 | 1.338 (4) | C31—C36 | 1.400 (4) |
C2—H2 | 0.9500 | C32—C33 | 1.393 (4) |
C3—C31 | 1.469 (4) | C32—H32 | 0.9500 |
C3—H3 | 0.9500 | C33—C34 | 1.374 (4) |
S11—C15 | 1.718 (3) | C33—H33 | 0.9500 |
S11—C12 | 1.733 (3) | C34—C35 | 1.390 (4) |
C12—C13 | 1.369 (4) | C34—Br34 | 1.898 (3) |
C13—C14 | 1.418 (4) | C35—C36 | 1.388 (4) |
C13—H13 | 0.9500 | C35—H35 | 0.9500 |
C14—C15 | 1.357 (4) | C36—H36 | 0.9500 |
O1—C1—C12 | 120.0 (2) | C14—C15—S11 | 113.4 (2) |
O1—C1—C2 | 123.2 (2) | Cl15—C15—S11 | 119.76 (16) |
C12—C1—C2 | 116.8 (2) | C32—C31—C36 | 117.8 (2) |
C3—C2—C1 | 121.4 (2) | C32—C31—C3 | 119.6 (2) |
C3—C2—H2 | 119.3 | C36—C31—C3 | 122.6 (2) |
C1—C2—H2 | 119.3 | C33—C32—C31 | 121.8 (3) |
C2—C3—C31 | 126.4 (3) | C33—C32—H32 | 119.1 |
C2—C3—H3 | 116.8 | C31—C32—H32 | 119.1 |
C31—C3—H3 | 116.8 | C34—C33—C32 | 118.4 (2) |
C15—S11—C12 | 90.62 (13) | C34—C33—H33 | 120.8 |
C13—C12—C1 | 131.2 (2) | C32—C33—H33 | 120.8 |
C13—C12—S11 | 111.4 (2) | C33—C34—C35 | 122.0 (2) |
C1—C12—S11 | 117.45 (19) | C33—C34—Br34 | 119.8 (2) |
C12—C13—C14 | 113.2 (2) | C35—C34—Br34 | 118.3 (2) |
C12—C13—H13 | 123.4 | C36—C35—C34 | 118.7 (3) |
C14—C13—H13 | 123.4 | C36—C35—H35 | 120.6 |
C15—C14—C13 | 111.4 (2) | C34—C35—H35 | 120.6 |
C15—C14—H14 | 124.3 | C35—C36—C31 | 121.3 (3) |
C13—C14—H14 | 124.3 | C35—C36—H36 | 119.4 |
C14—C15—Cl15 | 126.9 (2) | C31—C36—H36 | 119.4 |
O1—C1—C2—C3 | 6.9 (4) | C12—S11—C15—C14 | 0.1 (2) |
C12—C1—C2—C3 | −173.8 (3) | C12—S11—C15—Cl15 | −179.89 (18) |
C1—C2—C3—C31 | −175.7 (2) | C2—C3—C31—C32 | −179.7 (3) |
O1—C1—C12—C13 | 179.2 (3) | C2—C3—C31—C36 | 3.6 (4) |
C2—C1—C12—C13 | −0.1 (4) | C36—C31—C32—C33 | 1.9 (4) |
O1—C1—C12—S11 | −2.7 (4) | C3—C31—C32—C33 | −175.0 (2) |
C2—C1—C12—S11 | 177.99 (19) | C31—C32—C33—C34 | −1.3 (4) |
C15—S11—C12—C13 | −0.4 (2) | C32—C33—C34—C35 | 0.7 (4) |
C15—S11—C12—C1 | −178.8 (2) | C32—C33—C34—Br34 | −179.3 (2) |
C1—C12—C13—C14 | 178.7 (3) | C33—C34—C35—C36 | −0.7 (4) |
S11—C12—C13—C14 | 0.6 (3) | Br34—C34—C35—C36 | 179.3 (2) |
C12—C13—C14—C15 | −0.5 (3) | C34—C35—C36—C31 | 1.4 (4) |
C13—C14—C15—Cl15 | −179.8 (2) | C32—C31—C36—C35 | −2.0 (4) |
C13—C14—C15—S11 | 0.1 (3) | C3—C31—C36—C35 | 174.9 (3) |
C14H11BrO2S | F(000) = 648 |
Mr = 323.19 | Dx = 1.675 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.2726 (6) Å | Cell parameters from 4224 reflections |
b = 11.3948 (8) Å | θ = 3.4–32.7° |
c = 12.1472 (7) Å | µ = 3.36 mm−1 |
β = 93.273 (6)° | T = 173 K |
V = 1281.37 (14) Å3 | Block, colourless |
Z = 4 | 0.54 × 0.42 × 0.31 mm |
Agilent Eos Gemini diffractometer | 2914 reflections with I > 2σ(I) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.035 |
ω scans | θmax = 30.0°, θmin = 3.4° |
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012) | h = −13→12 |
Tmin = 0.216, Tmax = 0.353 | k = −15→16 |
8260 measured reflections | l = −16→17 |
3722 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.075 | w = 1/[σ2(Fo2) + (0.0293P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.003 |
3722 reflections | Δρmax = 0.49 e Å−3 |
164 parameters | Δρmin = −0.46 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.4180 (2) | 0.29186 (18) | 0.72203 (17) | 0.0205 (4) | |
O1 | 0.41175 (17) | 0.39954 (13) | 0.71617 (13) | 0.0310 (4) | |
C2 | 0.5005 (2) | 0.22053 (19) | 0.64696 (17) | 0.0217 (4) | |
H2 | 0.5078 | 0.1382 | 0.6584 | 0.026* | |
C3 | 0.5653 (2) | 0.26916 (19) | 0.56325 (15) | 0.0204 (4) | |
H3 | 0.5545 | 0.3516 | 0.5549 | 0.024* | |
S11 | 0.22557 (6) | 0.31118 (4) | 0.88317 (4) | 0.02124 (12) | |
C12 | 0.3390 (2) | 0.23001 (18) | 0.80567 (16) | 0.0180 (4) | |
C13 | 0.3392 (2) | 0.11390 (18) | 0.83642 (17) | 0.0232 (4) | |
H13 | 0.3952 | 0.0553 | 0.8031 | 0.028* | |
C14 | 0.2474 (2) | 0.09085 (19) | 0.92288 (17) | 0.0245 (5) | |
H14 | 0.2342 | 0.0155 | 0.9542 | 0.029* | |
C15 | 0.1805 (2) | 0.18936 (17) | 0.95556 (16) | 0.0192 (4) | |
Br15 | 0.05413 (2) | 0.20408 (2) | 1.06918 (2) | 0.02654 (8) | |
C31 | 0.6513 (2) | 0.20960 (18) | 0.48261 (16) | 0.0178 (4) | |
C32 | 0.7142 (2) | 0.27779 (18) | 0.40207 (16) | 0.0185 (4) | |
H32 | 0.6980 | 0.3601 | 0.3996 | 0.022* | |
C33 | 0.7994 (2) | 0.22577 (18) | 0.32643 (16) | 0.0192 (4) | |
C34 | 0.8214 (2) | 0.10536 (18) | 0.32844 (17) | 0.0242 (5) | |
H34 | 0.8796 | 0.0695 | 0.2761 | 0.029* | |
C35 | 0.7583 (2) | 0.0380 (2) | 0.40685 (17) | 0.0279 (5) | |
H35 | 0.7730 | −0.0445 | 0.4078 | 0.034* | |
C36 | 0.6737 (2) | 0.08920 (18) | 0.48427 (17) | 0.0237 (5) | |
H36 | 0.6314 | 0.0420 | 0.5382 | 0.028* | |
O33 | 0.86717 (16) | 0.28429 (13) | 0.24569 (13) | 0.0256 (3) | |
C37 | 0.8641 (3) | 0.40869 (19) | 0.24766 (19) | 0.0309 (5) | |
H37A | 0.9166 | 0.4394 | 0.1861 | 0.046* | |
H37B | 0.9099 | 0.4368 | 0.3174 | 0.046* | |
H37C | 0.7637 | 0.4358 | 0.2408 | 0.046* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0191 (10) | 0.0234 (11) | 0.0194 (10) | 0.0018 (8) | 0.0043 (8) | −0.0007 (9) |
O1 | 0.0368 (9) | 0.0211 (8) | 0.0371 (9) | 0.0005 (7) | 0.0201 (7) | 0.0008 (7) |
C2 | 0.0216 (10) | 0.0232 (10) | 0.0208 (10) | 0.0029 (9) | 0.0072 (8) | −0.0020 (9) |
C3 | 0.0200 (10) | 0.0211 (10) | 0.0204 (10) | 0.0034 (8) | 0.0038 (8) | −0.0012 (9) |
S11 | 0.0244 (3) | 0.0195 (2) | 0.0210 (3) | 0.0029 (2) | 0.0104 (2) | −0.0005 (2) |
C12 | 0.0177 (10) | 0.0208 (10) | 0.0161 (9) | 0.0013 (8) | 0.0051 (7) | −0.0045 (8) |
C13 | 0.0277 (11) | 0.0197 (10) | 0.0229 (11) | 0.0033 (9) | 0.0071 (8) | −0.0024 (9) |
C14 | 0.0305 (12) | 0.0203 (10) | 0.0237 (11) | 0.0000 (9) | 0.0099 (9) | 0.0023 (9) |
C15 | 0.0179 (10) | 0.0249 (11) | 0.0152 (9) | −0.0025 (8) | 0.0042 (7) | 0.0017 (8) |
Br15 | 0.02519 (12) | 0.03558 (14) | 0.01992 (12) | 0.00135 (9) | 0.01063 (8) | 0.00304 (9) |
C31 | 0.0153 (9) | 0.0249 (10) | 0.0133 (9) | −0.0004 (8) | 0.0020 (7) | −0.0016 (8) |
C32 | 0.0194 (10) | 0.0184 (9) | 0.0179 (9) | 0.0011 (8) | 0.0026 (7) | −0.0005 (8) |
C33 | 0.0175 (10) | 0.0233 (10) | 0.0169 (9) | 0.0017 (8) | 0.0029 (7) | 0.0029 (9) |
C34 | 0.0296 (11) | 0.0234 (10) | 0.0206 (10) | 0.0044 (9) | 0.0100 (8) | −0.0038 (9) |
C35 | 0.0384 (13) | 0.0199 (10) | 0.0265 (11) | 0.0052 (9) | 0.0103 (9) | 0.0017 (9) |
C36 | 0.0306 (11) | 0.0214 (11) | 0.0197 (10) | −0.0008 (9) | 0.0079 (8) | 0.0025 (9) |
O33 | 0.0301 (8) | 0.0232 (8) | 0.0252 (8) | 0.0013 (6) | 0.0166 (6) | 0.0030 (7) |
C37 | 0.0375 (13) | 0.0220 (11) | 0.0346 (13) | −0.0010 (10) | 0.0147 (10) | 0.0066 (10) |
C1—O1 | 1.230 (2) | C31—C36 | 1.388 (3) |
C1—C12 | 1.467 (3) | C31—C32 | 1.402 (3) |
C1—C2 | 1.469 (3) | C32—C33 | 1.380 (3) |
C2—C3 | 1.331 (3) | C32—H32 | 0.9500 |
C2—H2 | 0.9500 | C33—O33 | 1.368 (2) |
C3—C31 | 1.465 (3) | C33—C34 | 1.387 (3) |
C3—H3 | 0.9500 | C34—C35 | 1.379 (3) |
S11—C15 | 1.708 (2) | C34—H34 | 0.9500 |
S11—C12 | 1.7206 (19) | C35—C36 | 1.387 (3) |
C12—C13 | 1.375 (3) | C35—H35 | 0.9500 |
C13—C14 | 1.414 (3) | C36—H36 | 0.9500 |
C13—H13 | 0.9500 | O33—C37 | 1.418 (2) |
C14—C15 | 1.353 (3) | C37—H37A | 0.9800 |
C14—H14 | 0.9500 | C37—H37B | 0.9800 |
C15—Br15 | 1.8681 (18) | C37—H37C | 0.9800 |
O1—C1—C12 | 119.71 (18) | C32—C31—C3 | 118.29 (19) |
O1—C1—C2 | 122.72 (19) | C33—C32—C31 | 120.24 (19) |
C12—C1—C2 | 117.57 (19) | C33—C32—H32 | 119.9 |
C3—C2—C1 | 121.2 (2) | C31—C32—H32 | 119.9 |
C3—C2—H2 | 119.4 | O33—C33—C32 | 124.89 (19) |
C1—C2—H2 | 119.4 | O33—C33—C34 | 114.96 (17) |
C2—C3—C31 | 127.2 (2) | C32—C33—C34 | 120.15 (18) |
C2—C3—H3 | 116.4 | C35—C34—C33 | 119.68 (18) |
C31—C3—H3 | 116.4 | C35—C34—H34 | 120.2 |
C15—S11—C12 | 91.15 (10) | C33—C34—H34 | 120.2 |
C13—C12—C1 | 131.11 (18) | C34—C35—C36 | 120.8 (2) |
C13—C12—S11 | 111.13 (14) | C34—C35—H35 | 119.6 |
C1—C12—S11 | 117.76 (15) | C36—C35—H35 | 119.6 |
C12—C13—C14 | 112.87 (18) | C35—C36—C31 | 119.76 (19) |
C12—C13—H13 | 123.6 | C35—C36—H36 | 120.1 |
C14—C13—H13 | 123.6 | C31—C36—H36 | 120.1 |
C15—C14—C13 | 111.69 (18) | C33—O33—C37 | 117.69 (16) |
C15—C14—H14 | 124.2 | O33—C37—H37A | 109.5 |
C13—C14—H14 | 124.2 | O33—C37—H37B | 109.5 |
C14—C15—S11 | 113.17 (15) | H37A—C37—H37B | 109.5 |
C14—C15—Br15 | 127.49 (15) | O33—C37—H37C | 109.5 |
S11—C15—Br15 | 119.32 (11) | H37A—C37—H37C | 109.5 |
C36—C31—C32 | 119.33 (18) | H37B—C37—H37C | 109.5 |
C36—C31—C3 | 122.38 (18) | ||
O1—C1—C2—C3 | −4.7 (4) | C12—S11—C15—Br15 | 178.16 (13) |
C12—C1—C2—C3 | 174.42 (19) | C2—C3—C31—C36 | 1.0 (3) |
C1—C2—C3—C31 | 179.66 (19) | C2—C3—C31—C32 | −178.2 (2) |
O1—C1—C12—C13 | −172.7 (2) | C36—C31—C32—C33 | −1.0 (3) |
C2—C1—C12—C13 | 8.2 (4) | C3—C31—C32—C33 | 178.14 (18) |
O1—C1—C12—S11 | 6.5 (3) | C31—C32—C33—O33 | −179.10 (19) |
C2—C1—C12—S11 | −172.61 (16) | C31—C32—C33—C34 | 1.1 (3) |
C15—S11—C12—C13 | 0.11 (17) | O33—C33—C34—C35 | 179.8 (2) |
C15—S11—C12—C1 | −179.23 (17) | C32—C33—C34—C35 | −0.4 (3) |
C1—C12—C13—C14 | 179.2 (2) | C33—C34—C35—C36 | −0.4 (4) |
S11—C12—C13—C14 | 0.0 (2) | C34—C35—C36—C31 | 0.5 (4) |
C12—C13—C14—C15 | −0.2 (3) | C32—C31—C36—C35 | 0.2 (3) |
C13—C14—C15—S11 | 0.3 (3) | C3—C31—C36—C35 | −178.9 (2) |
C13—C14—C15—Br15 | −177.96 (15) | C32—C33—O33—C37 | 7.9 (3) |
C12—S11—C15—C14 | −0.22 (18) | C34—C33—O33—C37 | −172.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···O1i | 0.95 | 2.54 | 3.446 (3) | 159 |
Symmetry code: (i) −x+1, y−1/2, −z+3/2. |
Parameter | (I) | (II) | (III) | (IV) | (V) | (VI) |
Dihedral 1 | 2.74 (9) | 3.46 (18) | 2.80 (14) | 3.11 (18) | 3.66 (16) | 7.70 (13) |
Dihedral 2 | 10.23 (11) | 10.5 (2) | 3.71 (12) | 2.99915) | 9.74 (19) | 3.10 (11) |
Dihedral 3 | 11.62 (9) | 11.78 (16) | 6.49 (7) | 6.03 (9) | 11.96 (14) | 5.20 (13) |
C32—C33—O33 | 124.89 (19) | |||||
C34—C33—O33 | 114.96 (17) | |||||
C33—O33—C37 | 117.69 (16) | |||||
C33—C34—O34 | 116.33 (13) | 116.2 (2) | ||||
C35—C34—O34 | 123.98 (13) | 124.2 (2) | ||||
C34—O34—C37 | 117.57 (12) | 117.45 (18) | ||||
S11—C12—C1—C2 | ||||||
178.07 (10) | 177.34 (18) | -178.36 (12) | -178.48 (16) | 177.99 (19) | -172.61 (16) | |
C32—C33—O33—C37 | 7.9 (3) | |||||
C33—C34—C37—C38 | -97.5 (2) | -92.6 (3) | ||||
C33—C34—O34—C37 | -175.99 (15) | -176.45 (19) | ||||
C34—O34—C37—C38 | 169.60 (16) | 171.3 (2) |
`Dihedral 1' represents the dihedral angle between the spacer unit (C12,C1,C2,C3,C31) and the thienyl ring. `Dihedral 2' represents the dihedral angle between the spacer unit (C12,C1,C2,C3,C31) and the aryl ring. `Dihedral 3' represents the dihedral angle between the thienyl and aryl rings. |
Compound | D—H···A | D—H | H···A | D···A | D—H···A |
(III) | C36—H36···O6i | 0.95 | 2.52 | 3.4649 (18) | 173 |
(IV) | C36—H36···O6i | 0.95 | 2.52 | 3.464 (2) | 172 |
(VI) | C13—H13···O1ii | 0.95 | 2.54 | 3.446 (3) | 159 |
Symmetry codes: (i) x, -y + 3/2, z + 1/2; (ii) -x + 1, y - 1/2, -z + 3/2. |
Acknowledgements
VSN thanks the Government First Grade College, Kumta for research facilities. JPJ acknowledges the NSF–MRI program (grant No. 1039027) for funds to purchase the X-ray diffractometer.
References
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