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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615014205/dt3034sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615014205/dt3034Isup2.hkl
Contains datablock I

cdx

Chemdraw file https://doi.org/10.1107/S2053229615014205/dt3034Isup3.cdx
Supplementary material

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229615014205/dt3034sup4.pdf
Supplementary material

CCDC reference: 1062147

Computing details top

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).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
(2E)-1-(5-Chlorothiophen-2-yl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one top
Crystal data top
C15H14ClNOSF(000) = 608
Mr = 291.78Dx = 1.421 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 7.4534 (3) ÅCell parameters from 4889 reflections
b = 17.4357 (5) Åθ = 3.3–36.7°
c = 10.7079 (4) ŵ = 0.42 mm1
β = 101.479 (4)°T = 100 K
V = 1363.71 (9) Å3Block, clear light orange
Z = 40.3 × 0.28 × 0.25 mm
Data collection top
Oxford Xcalibur, Sapphire3
diffractometer
4168 independent reflections
Radiation source: Enhance (Mo) X-ray Source3566 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
Detector resolution: 16.0839 pixels mm-1θmax = 30.5°, θmin = 3.0°
ω scansh = 1010
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
k = 2423
Tmin = 0.621, Tmax = 1.000l = 1515
14824 measured reflections
Refinement top
Refinement on F2Primary atom site location: iterative
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H-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 reflectionsΔρmax = 0.47 e Å3
174 parametersΔρmin = 0.33 e Å3
0 restraints
Crystal data top
C15H14ClNOSV = 1363.71 (9) Å3
Mr = 291.78Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.4534 (3) ŵ = 0.42 mm1
b = 17.4357 (5) ÅT = 100 K
c = 10.7079 (4) Å0.3 × 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 = 1.000Rint = 0.044
14824 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.121H-atom parameters constrained
S = 1.11Δρmax = 0.47 e Å3
4168 reflectionsΔρmin = 0.33 e Å3
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
xyzUiso*/Ueq
S10.40034 (6)0.91323 (2)0.62777 (4)0.02111 (11)
Cl10.46365 (6)1.06406 (2)0.75786 (5)0.02994 (13)
O10.35358 (18)0.75891 (7)0.52462 (11)0.0265 (3)
C110.5722 (2)0.39297 (9)0.81616 (16)0.0203 (3)
C80.4997 (2)0.54205 (9)0.70788 (16)0.0189 (3)
C40.4696 (2)0.82923 (9)0.70938 (15)0.0178 (3)
C30.5490 (2)0.84343 (9)0.83443 (16)0.0207 (3)
H30.59490.80520.89260.025*
C20.5535 (2)0.92254 (9)0.86530 (16)0.0219 (3)
H20.60110.94230.94570.026*
C60.4996 (2)0.68607 (9)0.70502 (15)0.0191 (3)
H60.57110.68880.78670.023*
C130.4376 (2)0.47510 (9)0.63943 (16)0.0213 (3)
H130.37050.47980.55670.026*
C10.4793 (2)0.96594 (9)0.76231 (16)0.0210 (3)
N10.6078 (2)0.32169 (8)0.86870 (15)0.0259 (3)
C150.6982 (3)0.31351 (10)1.00153 (17)0.0277 (4)
H15A0.82000.33401.01320.042*
H15B0.70400.26021.02440.042*
H15C0.63040.34091.05460.042*
C120.4727 (2)0.40269 (9)0.69053 (16)0.0217 (3)
H120.43030.35990.64170.026*
C140.5438 (3)0.25365 (10)0.79621 (19)0.0288 (4)
H14A0.41240.25250.77940.043*
H14B0.59080.20890.84410.043*
H14C0.58560.25430.71700.043*
C100.6336 (2)0.46014 (9)0.88655 (16)0.0204 (3)
H100.69830.45570.97000.024*
C90.5988 (2)0.53181 (9)0.83301 (16)0.0204 (3)
H90.64220.57480.88110.025*
C50.4359 (2)0.75694 (9)0.63720 (15)0.0193 (3)
C70.4563 (2)0.61662 (9)0.65096 (16)0.0199 (3)
H70.39090.61690.56740.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0247 (2)0.01391 (18)0.0229 (2)0.00022 (14)0.00031 (15)0.00165 (13)
Cl10.0324 (2)0.01186 (19)0.0449 (3)0.00114 (15)0.00595 (19)0.00224 (15)
O10.0354 (7)0.0188 (6)0.0220 (6)0.0035 (5)0.0021 (5)0.0006 (4)
C110.0198 (8)0.0149 (7)0.0273 (8)0.0005 (6)0.0070 (6)0.0005 (6)
C80.0183 (7)0.0147 (7)0.0239 (7)0.0000 (6)0.0044 (6)0.0018 (6)
C40.0176 (7)0.0137 (7)0.0212 (7)0.0007 (5)0.0019 (6)0.0009 (5)
C30.0214 (8)0.0155 (7)0.0234 (7)0.0013 (6)0.0000 (6)0.0004 (6)
C20.0202 (8)0.0173 (7)0.0258 (8)0.0008 (6)0.0013 (6)0.0051 (6)
C60.0208 (8)0.0157 (7)0.0207 (7)0.0011 (6)0.0039 (6)0.0004 (5)
C130.0203 (8)0.0180 (7)0.0247 (8)0.0013 (6)0.0021 (6)0.0025 (6)
C10.0195 (8)0.0125 (7)0.0307 (8)0.0008 (6)0.0042 (6)0.0036 (6)
N10.0322 (8)0.0124 (6)0.0319 (8)0.0029 (5)0.0035 (6)0.0011 (5)
C150.0381 (10)0.0195 (8)0.0270 (8)0.0024 (7)0.0098 (7)0.0040 (6)
C120.0230 (8)0.0143 (7)0.0273 (8)0.0021 (6)0.0037 (6)0.0035 (6)
C140.0306 (9)0.0132 (7)0.0413 (10)0.0027 (7)0.0037 (8)0.0021 (7)
C100.0231 (8)0.0165 (7)0.0217 (7)0.0008 (6)0.0047 (6)0.0016 (6)
C90.0226 (8)0.0143 (7)0.0242 (7)0.0003 (6)0.0043 (6)0.0047 (6)
C50.0200 (8)0.0148 (7)0.0228 (7)0.0021 (6)0.0034 (6)0.0008 (5)
C70.0188 (7)0.0169 (7)0.0235 (8)0.0006 (6)0.0032 (6)0.0011 (6)
Geometric parameters (Å, º) top
S1—C41.7309 (16)C6—C51.464 (2)
S1—C11.7114 (17)C6—C71.353 (2)
Cl1—C11.7148 (16)C13—H130.9300
O1—C51.2397 (19)C13—C121.380 (2)
C11—N11.368 (2)N1—C151.455 (2)
C11—C121.411 (2)N1—C141.446 (2)
C11—C101.418 (2)C15—H15A0.9600
C8—C131.407 (2)C15—H15B0.9600
C8—C91.407 (2)C15—H15C0.9600
C8—C71.445 (2)C12—H120.9300
C4—C31.374 (2)C14—H14A0.9600
C4—C51.474 (2)C14—H14B0.9600
C3—H30.9300C14—H14C0.9600
C3—C21.417 (2)C10—H100.9300
C2—H20.9300C10—C91.378 (2)
C2—C11.361 (2)C9—H90.9300
C6—H60.9300C7—H70.9300
C1—S1—C490.65 (8)N1—C15—H15A109.5
N1—C11—C12121.54 (15)N1—C15—H15B109.5
N1—C11—C10121.05 (15)N1—C15—H15C109.5
C12—C11—C10117.41 (14)H15A—C15—H15B109.5
C13—C8—C9116.55 (15)H15A—C15—H15C109.5
C13—C8—C7120.27 (15)H15B—C15—H15C109.5
C9—C8—C7123.15 (14)C11—C12—H12119.7
C3—C4—S1111.52 (12)C13—C12—C11120.66 (15)
C3—C4—C5131.33 (14)C13—C12—H12119.7
C5—C4—S1117.16 (12)N1—C14—H14A109.5
C4—C3—H3123.6N1—C14—H14B109.5
C4—C3—C2112.84 (14)N1—C14—H14C109.5
C2—C3—H3123.6H14A—C14—H14B109.5
C3—C2—H2124.3H14A—C14—H14C109.5
C1—C2—C3111.42 (14)H14B—C14—H14C109.5
C1—C2—H2124.3C11—C10—H10119.5
C5—C6—H6119.4C9—C10—C11120.90 (15)
C7—C6—H6119.4C9—C10—H10119.5
C7—C6—C5121.13 (15)C8—C9—H9119.0
C8—C13—H13118.8C10—C9—C8122.08 (15)
C12—C13—C8122.39 (16)C10—C9—H9119.0
C12—C13—H13118.8O1—C5—C4119.08 (14)
S1—C1—Cl1120.15 (10)O1—C5—C6123.69 (14)
C2—C1—S1113.57 (12)C6—C5—C4117.21 (14)
C2—C1—Cl1126.27 (13)C8—C7—H7116.2
C11—N1—C15120.35 (14)C6—C7—C8127.62 (15)
C11—N1—C14120.56 (15)C6—C7—H7116.2
C14—N1—C15118.92 (14)
S1—C4—C3—C20.32 (19)N1—C11—C12—C13179.75 (16)
S1—C4—C5—O13.2 (2)N1—C11—C10—C9179.49 (16)
S1—C4—C5—C6178.11 (12)C12—C11—N1—C15175.22 (16)
C11—C10—C9—C80.8 (3)C12—C11—N1—C140.0 (3)
C8—C13—C12—C110.7 (3)C12—C11—C10—C90.8 (2)
C4—S1—C1—Cl1178.52 (11)C10—C11—N1—C154.5 (3)
C4—S1—C1—C20.55 (14)C10—C11—N1—C14179.73 (16)
C4—C3—C2—C10.7 (2)C10—C11—C12—C130.0 (3)
C3—C4—C5—O1176.95 (17)C9—C8—C13—C120.7 (2)
C3—C4—C5—C61.8 (3)C9—C8—C7—C60.5 (3)
C3—C2—C1—S10.8 (2)C5—C4—C3—C2179.78 (17)
C3—C2—C1—Cl1178.19 (13)C5—C6—C7—C8176.23 (16)
C13—C8—C9—C100.1 (2)C7—C8—C13—C12178.80 (16)
C13—C8—C7—C6177.51 (16)C7—C8—C9—C10177.96 (16)
C1—S1—C4—C30.12 (14)C7—C6—C5—O16.3 (3)
C1—S1—C4—C5179.80 (13)C7—C6—C5—C4172.34 (15)

Experimental details

Crystal data
Chemical formulaC15H14ClNOS
Mr291.78
Crystal system, space groupMonoclinic, P21/n
Temperature (K)100
a, b, c (Å)7.4534 (3), 17.4357 (5), 10.7079 (4)
β (°) 101.479 (4)
V3)1363.71 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.42
Crystal size (mm)0.3 × 0.28 × 0.25
Data collection
DiffractometerOxford Xcalibur, Sapphire3
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2013)
Tmin, Tmax0.621, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
14824, 4168, 3566
Rint0.044
(sin θ/λ)max1)0.714
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.121, 1.11
No. of reflections4168
No. of parameters174
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.47, 0.33

Computer programs: CrysAlis PRO (Agilent, 2013), olex2.solve (Bourhis et al., 2013), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

 

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