The solid-state emmissive chalcone (2E)-1-(5-chloro­thiophen-2-yl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one

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.

Computing details

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

(2E)-1-(5-Chlorothiophen-2-yl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one

Crystal data

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) Å^3	Block, clear light orange
Z = 4	0.3 × 0.28 × 0.25 mm

Data collection

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

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.121	w = 1/[σ^2(Fo^2) + (0.0571P)^2 + 0.4304P] where P = (Fo^2 + 2Fc^2)/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

Special details

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)