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Orange rectangular blocks suitable for X-ray diffraction analysis were obtained for the previously reported [Ahmad & Bano (2011). Int. J. ChemTech Res. 3, 1470–1478] title chalcone, C15H14ClNOS. This solid-emissive chalcone exhibits a planar structure and the bond parameters are compared with related compounds already described in the literature. The determination of the structure of this chalcone is quite relevant because it will play an important role in theoretical calculations to investigate potential two-photon absorption processes and could also be useful for studying the interaction of such compounds with a biological target.
Supporting information
CCDC reference: 1062147
Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: olex2.solve (Bourhis et al., 2013); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
(2
E)-1-(5-Chlorothiophen-2-yl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one
top
Crystal data top
C15H14ClNOS | F(000) = 608 |
Mr = 291.78 | Dx = 1.421 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.4534 (3) Å | Cell parameters from 4889 reflections |
b = 17.4357 (5) Å | θ = 3.3–36.7° |
c = 10.7079 (4) Å | µ = 0.42 mm−1 |
β = 101.479 (4)° | T = 100 K |
V = 1363.71 (9) Å3 | Block, clear light orange |
Z = 4 | 0.3 × 0.28 × 0.25 mm |
Data collection top
Oxford Xcalibur, Sapphire3 diffractometer | 4168 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3566 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
Detector resolution: 16.0839 pixels mm-1 | θmax = 30.5°, θmin = 3.0° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | k = −24→23 |
Tmin = 0.621, Tmax = 1.000 | l = −15→15 |
14824 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.050 | H-atom parameters constrained |
wR(F2) = 0.121 | w = 1/[σ2(Fo2) + (0.0571P)2 + 0.4304P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max = 0.002 |
4168 reflections | Δρmax = 0.47 e Å−3 |
174 parameters | Δρmin = −0.33 e Å−3 |
0 restraints | |
Crystal data top
C15H14ClNOS | V = 1363.71 (9) Å3 |
Mr = 291.78 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.4534 (3) Å | µ = 0.42 mm−1 |
b = 17.4357 (5) Å | T = 100 K |
c = 10.7079 (4) Å | 0.3 × 0.28 × 0.25 mm |
β = 101.479 (4)° | |
Data collection top
Oxford Xcalibur, Sapphire3 diffractometer | 4168 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | 3566 reflections with I > 2σ(I) |
Tmin = 0.621, Tmax = 1.000 | Rint = 0.044 |
14824 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.11 | Δρmax = 0.47 e Å−3 |
4168 reflections | Δρmin = −0.33 e Å−3 |
174 parameters | |
Special details top
Experimental. Absorption correction: CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb 1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.40034 (6) | 0.91323 (2) | 0.62777 (4) | 0.02111 (11) | |
Cl1 | 0.46365 (6) | 1.06406 (2) | 0.75786 (5) | 0.02994 (13) | |
O1 | 0.35358 (18) | 0.75891 (7) | 0.52462 (11) | 0.0265 (3) | |
C11 | 0.5722 (2) | 0.39297 (9) | 0.81616 (16) | 0.0203 (3) | |
C8 | 0.4997 (2) | 0.54205 (9) | 0.70788 (16) | 0.0189 (3) | |
C4 | 0.4696 (2) | 0.82923 (9) | 0.70938 (15) | 0.0178 (3) | |
C3 | 0.5490 (2) | 0.84343 (9) | 0.83443 (16) | 0.0207 (3) | |
H3 | 0.5949 | 0.8052 | 0.8926 | 0.025* | |
C2 | 0.5535 (2) | 0.92254 (9) | 0.86530 (16) | 0.0219 (3) | |
H2 | 0.6011 | 0.9423 | 0.9457 | 0.026* | |
C6 | 0.4996 (2) | 0.68607 (9) | 0.70502 (15) | 0.0191 (3) | |
H6 | 0.5711 | 0.6888 | 0.7867 | 0.023* | |
C13 | 0.4376 (2) | 0.47510 (9) | 0.63943 (16) | 0.0213 (3) | |
H13 | 0.3705 | 0.4798 | 0.5567 | 0.026* | |
C1 | 0.4793 (2) | 0.96594 (9) | 0.76231 (16) | 0.0210 (3) | |
N1 | 0.6078 (2) | 0.32169 (8) | 0.86870 (15) | 0.0259 (3) | |
C15 | 0.6982 (3) | 0.31351 (10) | 1.00153 (17) | 0.0277 (4) | |
H15A | 0.8200 | 0.3340 | 1.0132 | 0.042* | |
H15B | 0.7040 | 0.2602 | 1.0244 | 0.042* | |
H15C | 0.6304 | 0.3409 | 1.0546 | 0.042* | |
C12 | 0.4727 (2) | 0.40269 (9) | 0.69053 (16) | 0.0217 (3) | |
H12 | 0.4303 | 0.3599 | 0.6417 | 0.026* | |
C14 | 0.5438 (3) | 0.25365 (10) | 0.79621 (19) | 0.0288 (4) | |
H14A | 0.4124 | 0.2525 | 0.7794 | 0.043* | |
H14B | 0.5908 | 0.2089 | 0.8441 | 0.043* | |
H14C | 0.5856 | 0.2543 | 0.7170 | 0.043* | |
C10 | 0.6336 (2) | 0.46014 (9) | 0.88655 (16) | 0.0204 (3) | |
H10 | 0.6983 | 0.4557 | 0.9700 | 0.024* | |
C9 | 0.5988 (2) | 0.53181 (9) | 0.83301 (16) | 0.0204 (3) | |
H9 | 0.6422 | 0.5748 | 0.8811 | 0.025* | |
C5 | 0.4359 (2) | 0.75694 (9) | 0.63720 (15) | 0.0193 (3) | |
C7 | 0.4563 (2) | 0.61662 (9) | 0.65096 (16) | 0.0199 (3) | |
H7 | 0.3909 | 0.6169 | 0.5674 | 0.024* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0247 (2) | 0.01391 (18) | 0.0229 (2) | 0.00022 (14) | 0.00031 (15) | 0.00165 (13) |
Cl1 | 0.0324 (2) | 0.01186 (19) | 0.0449 (3) | 0.00114 (15) | 0.00595 (19) | −0.00224 (15) |
O1 | 0.0354 (7) | 0.0188 (6) | 0.0220 (6) | −0.0035 (5) | −0.0021 (5) | −0.0006 (4) |
C11 | 0.0198 (8) | 0.0149 (7) | 0.0273 (8) | −0.0005 (6) | 0.0070 (6) | −0.0005 (6) |
C8 | 0.0183 (7) | 0.0147 (7) | 0.0239 (7) | 0.0000 (6) | 0.0044 (6) | −0.0018 (6) |
C4 | 0.0176 (7) | 0.0137 (7) | 0.0212 (7) | −0.0007 (5) | 0.0019 (6) | 0.0009 (5) |
C3 | 0.0214 (8) | 0.0155 (7) | 0.0234 (7) | 0.0013 (6) | 0.0000 (6) | −0.0004 (6) |
C2 | 0.0202 (8) | 0.0173 (7) | 0.0258 (8) | 0.0008 (6) | −0.0013 (6) | −0.0051 (6) |
C6 | 0.0208 (8) | 0.0157 (7) | 0.0207 (7) | −0.0011 (6) | 0.0039 (6) | −0.0004 (5) |
C13 | 0.0203 (8) | 0.0180 (7) | 0.0247 (8) | −0.0013 (6) | 0.0021 (6) | −0.0025 (6) |
C1 | 0.0195 (8) | 0.0125 (7) | 0.0307 (8) | −0.0008 (6) | 0.0042 (6) | −0.0036 (6) |
N1 | 0.0322 (8) | 0.0124 (6) | 0.0319 (8) | −0.0029 (5) | 0.0035 (6) | 0.0011 (5) |
C15 | 0.0381 (10) | 0.0195 (8) | 0.0270 (8) | 0.0024 (7) | 0.0098 (7) | 0.0040 (6) |
C12 | 0.0230 (8) | 0.0143 (7) | 0.0273 (8) | −0.0021 (6) | 0.0037 (6) | −0.0035 (6) |
C14 | 0.0306 (9) | 0.0132 (7) | 0.0413 (10) | −0.0027 (7) | 0.0037 (8) | −0.0021 (7) |
C10 | 0.0231 (8) | 0.0165 (7) | 0.0217 (7) | 0.0008 (6) | 0.0047 (6) | −0.0016 (6) |
C9 | 0.0226 (8) | 0.0143 (7) | 0.0242 (7) | −0.0003 (6) | 0.0043 (6) | −0.0047 (6) |
C5 | 0.0200 (8) | 0.0148 (7) | 0.0228 (7) | −0.0021 (6) | 0.0034 (6) | −0.0008 (5) |
C7 | 0.0188 (7) | 0.0169 (7) | 0.0235 (8) | −0.0006 (6) | 0.0032 (6) | −0.0011 (6) |
Geometric parameters (Å, º) top
S1—C4 | 1.7309 (16) | C6—C5 | 1.464 (2) |
S1—C1 | 1.7114 (17) | C6—C7 | 1.353 (2) |
Cl1—C1 | 1.7148 (16) | C13—H13 | 0.9300 |
O1—C5 | 1.2397 (19) | C13—C12 | 1.380 (2) |
C11—N1 | 1.368 (2) | N1—C15 | 1.455 (2) |
C11—C12 | 1.411 (2) | N1—C14 | 1.446 (2) |
C11—C10 | 1.418 (2) | C15—H15A | 0.9600 |
C8—C13 | 1.407 (2) | C15—H15B | 0.9600 |
C8—C9 | 1.407 (2) | C15—H15C | 0.9600 |
C8—C7 | 1.445 (2) | C12—H12 | 0.9300 |
C4—C3 | 1.374 (2) | C14—H14A | 0.9600 |
C4—C5 | 1.474 (2) | C14—H14B | 0.9600 |
C3—H3 | 0.9300 | C14—H14C | 0.9600 |
C3—C2 | 1.417 (2) | C10—H10 | 0.9300 |
C2—H2 | 0.9300 | C10—C9 | 1.378 (2) |
C2—C1 | 1.361 (2) | C9—H9 | 0.9300 |
C6—H6 | 0.9300 | C7—H7 | 0.9300 |
| | | |
C1—S1—C4 | 90.65 (8) | N1—C15—H15A | 109.5 |
N1—C11—C12 | 121.54 (15) | N1—C15—H15B | 109.5 |
N1—C11—C10 | 121.05 (15) | N1—C15—H15C | 109.5 |
C12—C11—C10 | 117.41 (14) | H15A—C15—H15B | 109.5 |
C13—C8—C9 | 116.55 (15) | H15A—C15—H15C | 109.5 |
C13—C8—C7 | 120.27 (15) | H15B—C15—H15C | 109.5 |
C9—C8—C7 | 123.15 (14) | C11—C12—H12 | 119.7 |
C3—C4—S1 | 111.52 (12) | C13—C12—C11 | 120.66 (15) |
C3—C4—C5 | 131.33 (14) | C13—C12—H12 | 119.7 |
C5—C4—S1 | 117.16 (12) | N1—C14—H14A | 109.5 |
C4—C3—H3 | 123.6 | N1—C14—H14B | 109.5 |
C4—C3—C2 | 112.84 (14) | N1—C14—H14C | 109.5 |
C2—C3—H3 | 123.6 | H14A—C14—H14B | 109.5 |
C3—C2—H2 | 124.3 | H14A—C14—H14C | 109.5 |
C1—C2—C3 | 111.42 (14) | H14B—C14—H14C | 109.5 |
C1—C2—H2 | 124.3 | C11—C10—H10 | 119.5 |
C5—C6—H6 | 119.4 | C9—C10—C11 | 120.90 (15) |
C7—C6—H6 | 119.4 | C9—C10—H10 | 119.5 |
C7—C6—C5 | 121.13 (15) | C8—C9—H9 | 119.0 |
C8—C13—H13 | 118.8 | C10—C9—C8 | 122.08 (15) |
C12—C13—C8 | 122.39 (16) | C10—C9—H9 | 119.0 |
C12—C13—H13 | 118.8 | O1—C5—C4 | 119.08 (14) |
S1—C1—Cl1 | 120.15 (10) | O1—C5—C6 | 123.69 (14) |
C2—C1—S1 | 113.57 (12) | C6—C5—C4 | 117.21 (14) |
C2—C1—Cl1 | 126.27 (13) | C8—C7—H7 | 116.2 |
C11—N1—C15 | 120.35 (14) | C6—C7—C8 | 127.62 (15) |
C11—N1—C14 | 120.56 (15) | C6—C7—H7 | 116.2 |
C14—N1—C15 | 118.92 (14) | | |
| | | |
S1—C4—C3—C2 | 0.32 (19) | N1—C11—C12—C13 | 179.75 (16) |
S1—C4—C5—O1 | −3.2 (2) | N1—C11—C10—C9 | 179.49 (16) |
S1—C4—C5—C6 | 178.11 (12) | C12—C11—N1—C15 | −175.22 (16) |
C11—C10—C9—C8 | 0.8 (3) | C12—C11—N1—C14 | 0.0 (3) |
C8—C13—C12—C11 | 0.7 (3) | C12—C11—C10—C9 | −0.8 (2) |
C4—S1—C1—Cl1 | 178.52 (11) | C10—C11—N1—C15 | 4.5 (3) |
C4—S1—C1—C2 | −0.55 (14) | C10—C11—N1—C14 | 179.73 (16) |
C4—C3—C2—C1 | −0.7 (2) | C10—C11—C12—C13 | 0.0 (3) |
C3—C4—C5—O1 | 176.95 (17) | C9—C8—C13—C12 | −0.7 (2) |
C3—C4—C5—C6 | −1.8 (3) | C9—C8—C7—C6 | −0.5 (3) |
C3—C2—C1—S1 | 0.8 (2) | C5—C4—C3—C2 | −179.78 (17) |
C3—C2—C1—Cl1 | −178.19 (13) | C5—C6—C7—C8 | −176.23 (16) |
C13—C8—C9—C10 | −0.1 (2) | C7—C8—C13—C12 | −178.80 (16) |
C13—C8—C7—C6 | 177.51 (16) | C7—C8—C9—C10 | 177.96 (16) |
C1—S1—C4—C3 | 0.12 (14) | C7—C6—C5—O1 | −6.3 (3) |
C1—S1—C4—C5 | −179.80 (13) | C7—C6—C5—C4 | 172.34 (15) |
Experimental details
Crystal data |
Chemical formula | C15H14ClNOS |
Mr | 291.78 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 100 |
a, b, c (Å) | 7.4534 (3), 17.4357 (5), 10.7079 (4) |
β (°) | 101.479 (4) |
V (Å3) | 1363.71 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.42 |
Crystal size (mm) | 0.3 × 0.28 × 0.25 |
|
Data collection |
Diffractometer | Oxford Xcalibur, Sapphire3 diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2013) |
Tmin, Tmax | 0.621, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14824, 4168, 3566 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.714 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.121, 1.11 |
No. of reflections | 4168 |
No. of parameters | 174 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.47, −0.33 |
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