(E)-1-(Benzo[d][1,3]dioxol-5-yl)-3-([2,2′-bi­thio­phen]-5-yl)prop-2-en-1-one: crystal structure, UV–Vis analysis and theoretical studies of a new π-conjugated chalcone

The essentially planar chalcone unit adopts an s-cis configuration with respect to the carbonyl group within the ethyl­enic bridge. In the crystal, weak C—H...π inter­actions connect the mol­ecules into zigzag chains along the a-axis direction.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.058
• wR factor = 0.164
• Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C16      --C17      .       14.3 s.u.

Alert level C
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of         S2 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C16 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00524 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      9.429 Check

Alert level G
PLAT013_ALERT_1_G N.O.K.   _shelx_hkl_checksum Found in CIF ......     Please Check
PLAT128_ALERT_4_G Alternate Setting for Input Space Group  P21/c        P21/n Note
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O1             105.6 Degree
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O2             105.3 Degree
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          8 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(E)-1-(Benzo[d][1,3]dioxol-5-yl)-3-([2,2'-bithiophen]-5-yl)prop-2-en-1-one

Crystal data

C18H12O3S2	F(000) = 704
Mr = 340.40	Dx = 1.471 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.030 (1) Å	Cell parameters from 3229 reflections
b = 24.875 (5) Å	θ = 2.6–19.6°
c = 11.239 (2) Å	µ = 0.36 mm^−1
β = 114.249 (2)°	T = 296 K
V = 1537.1 (5) Å^3	Plate, yellow
Z = 4	0.19 × 0.15 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer	2096 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.078
Absorption correction: multi-scan (SADABS; Bruker, 2009)	θmax = 26.0°, θmin = 2.2°
Tmin = 0.875, Tmax = 0.924	h = −7→7
30820 measured reflections	k = −30→30
3024 independent reflections	l = −13→13

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.058	H-atom parameters constrained
wR(F^2) = 0.164	w = 1/[σ^2(Fo^2) + (0.074P)^2 + 1.2156P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
3024 reflections	Δρmax = 0.41 e Å^−3
208 parameters	Δρmin = −0.47 e Å^−3

Special details

Experimental. The following wavelength and cell were deduced by SADABS from the direction cosines etc. They are given here for emergency use only: CELL 0.71075 11.261 24.951 12.083 90.028 114.196 90.000

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.28791 (16)	0.61675 (4)	−0.12250 (9)	0.0500 (3)
S2	0.7476 (2)	0.71610 (5)	−0.24635 (12)	0.0759 (4)
O1	0.3608 (5)	0.35799 (12)	0.5854 (3)	0.0715 (8)
O2	0.7813 (5)	0.35937 (12)	0.6897 (3)	0.0693 (8)
O3	0.1080 (4)	0.48699 (11)	0.1984 (3)	0.0628 (8)
C1	0.3315 (6)	0.42199 (14)	0.4126 (3)	0.0458 (8)
H1A	0.1626	0.4211	0.3711	0.055*
C2	0.4540 (6)	0.39239 (14)	0.5213 (3)	0.0468 (8)
C3	0.5656 (8)	0.33666 (17)	0.6914 (4)	0.0681 (11)
H3A	0.5690	0.2979	0.6837	0.082*
H3B	0.5551	0.3452	0.7731	0.082*
C4	0.7034 (7)	0.39318 (14)	0.5843 (3)	0.0495 (9)
C5	0.8413 (6)	0.42354 (15)	0.5408 (4)	0.0549 (9)
H5A	1.0100	0.4239	0.5838	0.066*
C6	0.7201 (6)	0.45425 (14)	0.4288 (3)	0.0478 (8)
H6A	0.8102	0.4754	0.3965	0.057*
C7	0.4692 (6)	0.45409 (13)	0.3647 (3)	0.0388 (7)
C8	0.3316 (6)	0.48707 (13)	0.2464 (3)	0.0439 (8)
C9	0.4651 (6)	0.52000 (14)	0.1886 (3)	0.0472 (8)
H9A	0.6341	0.5210	0.2290	0.057*
C10	0.3511 (6)	0.54804 (13)	0.0810 (3)	0.0443 (8)
H10A	0.1824	0.5455	0.0418	0.053*
C11	0.4651 (6)	0.58250 (13)	0.0185 (3)	0.0420 (8)
C12	0.7044 (6)	0.59448 (15)	0.0536 (3)	0.0502 (9)
H12A	0.8296	0.5800	0.1266	0.060*
C13	0.7433 (6)	0.63090 (15)	−0.0313 (4)	0.0514 (9)
H13A	0.8971	0.6429	−0.0195	0.062*
C14	0.5365 (6)	0.64701 (13)	−0.1323 (3)	0.0406 (8)
C15	0.5055 (6)	0.68374 (13)	−0.2391 (3)	0.0440 (8)
C16	0.2850 (6)	0.69828 (13)	−0.3490 (3)	0.0414 (8)
H16A	0.1299	0.6861	−0.3641	0.050*
C17	0.3416 (9)	0.73361 (17)	−0.4296 (4)	0.0707 (12)
H17A	0.2237	0.7470	−0.5069	0.085*
C18	0.5754 (9)	0.74663 (17)	−0.3879 (4)	0.0745 (13)
H18A	0.6365	0.7699	−0.4319	0.089*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0423 (5)	0.0579 (6)	0.0427 (5)	−0.0005 (4)	0.0104 (4)	0.0114 (4)
S2	0.0742 (8)	0.0772 (8)	0.0827 (9)	−0.0029 (6)	0.0389 (7)	0.0186 (6)
O1	0.0704 (18)	0.0748 (19)	0.0736 (19)	0.0013 (15)	0.0338 (16)	0.0314 (16)
O2	0.0705 (18)	0.0690 (19)	0.0551 (17)	0.0058 (15)	0.0124 (14)	0.0231 (14)
O3	0.0410 (14)	0.0757 (19)	0.0598 (17)	−0.0031 (12)	0.0086 (12)	0.0221 (14)
C1	0.0394 (18)	0.050 (2)	0.046 (2)	0.0012 (15)	0.0160 (15)	0.0002 (16)
C2	0.053 (2)	0.043 (2)	0.048 (2)	−0.0008 (16)	0.0243 (17)	0.0030 (16)
C3	0.094 (3)	0.057 (3)	0.054 (2)	0.003 (2)	0.031 (2)	0.011 (2)
C4	0.058 (2)	0.044 (2)	0.0394 (19)	0.0029 (17)	0.0126 (17)	0.0026 (15)
C5	0.0418 (19)	0.058 (2)	0.053 (2)	−0.0009 (17)	0.0081 (17)	0.0032 (19)
C6	0.0446 (19)	0.049 (2)	0.046 (2)	−0.0024 (15)	0.0139 (16)	0.0039 (16)
C7	0.0427 (17)	0.0354 (17)	0.0361 (17)	−0.0030 (14)	0.0139 (14)	−0.0039 (14)
C8	0.0471 (19)	0.0412 (19)	0.0389 (18)	−0.0015 (15)	0.0131 (15)	−0.0026 (15)
C9	0.0430 (18)	0.049 (2)	0.046 (2)	−0.0044 (15)	0.0148 (16)	0.0025 (17)
C10	0.0440 (18)	0.0462 (19)	0.0408 (19)	−0.0014 (15)	0.0155 (15)	0.0005 (16)
C11	0.0443 (18)	0.0437 (19)	0.0364 (18)	0.0052 (14)	0.0152 (15)	0.0000 (15)
C12	0.0418 (19)	0.061 (2)	0.042 (2)	0.0075 (16)	0.0112 (15)	0.0116 (17)
C13	0.0394 (18)	0.059 (2)	0.055 (2)	0.0030 (16)	0.0191 (17)	0.0067 (18)
C14	0.0456 (18)	0.0368 (18)	0.0411 (18)	0.0019 (14)	0.0196 (15)	−0.0016 (14)
C15	0.056 (2)	0.0369 (18)	0.0430 (19)	0.0032 (15)	0.0236 (16)	−0.0011 (15)
C16	0.0505 (19)	0.0413 (19)	0.0311 (17)	−0.0042 (15)	0.0155 (15)	0.0005 (14)
C17	0.091 (3)	0.067 (3)	0.048 (2)	0.024 (2)	0.021 (2)	0.006 (2)
C18	0.115 (4)	0.059 (3)	0.066 (3)	0.004 (3)	0.055 (3)	0.014 (2)

Geometric parameters (Å, º)

S1—C14	1.720 (3)	C6—H6A	0.9300
S1—C11	1.728 (3)	C7—C8	1.491 (4)
S2—C18	1.682 (4)	C8—C9	1.473 (5)
S2—C15	1.698 (3)	C9—C10	1.318 (5)
O1—C2	1.378 (4)	C9—H9A	0.9300
O1—C3	1.420 (5)	C10—C11	1.448 (4)
O2—C4	1.369 (4)	C10—H10A	0.9300
O2—C3	1.425 (5)	C11—C12	1.364 (5)
O3—C8	1.229 (4)	C12—C13	1.404 (5)
C1—C2	1.356 (5)	C12—H12A	0.9300
C1—C7	1.409 (5)	C13—C14	1.357 (5)
C1—H1A	0.9300	C13—H13A	0.9300
C2—C4	1.375 (5)	C14—C15	1.458 (5)
C3—H3A	0.9700	C15—C16	1.441 (5)
C3—H3B	0.9700	C16—C17	1.401 (5)
C4—C5	1.355 (5)	C16—H16A	0.9300
C5—C6	1.395 (5)	C17—C18	1.330 (6)
C5—H5A	0.9300	C17—H17A	0.9300
C6—C7	1.383 (4)	C18—H18A	0.9300
C14—S1—C11	92.72 (16)	C10—C9—C8	121.6 (3)
C18—S2—C15	92.9 (2)	C10—C9—H9A	119.2
C2—O1—C3	105.6 (3)	C8—C9—H9A	119.2
C4—O2—C3	105.3 (3)	C9—C10—C11	125.8 (3)
C2—C1—C7	117.6 (3)	C9—C10—H10A	117.1
C2—C1—H1A	121.2	C11—C10—H10A	117.1
C7—C1—H1A	121.2	C12—C11—C10	130.2 (3)
C1—C2—C4	122.1 (3)	C12—C11—S1	109.9 (3)
C1—C2—O1	128.3 (3)	C10—C11—S1	119.9 (2)
C4—C2—O1	109.6 (3)	C11—C12—C13	113.4 (3)
O1—C3—O2	109.0 (3)	C11—C12—H12A	123.3
O1—C3—H3A	109.9	C13—C12—H12A	123.3
O2—C3—H3A	109.9	C14—C13—C12	113.9 (3)
O1—C3—H3B	109.9	C14—C13—H13A	123.0
O2—C3—H3B	109.9	C12—C13—H13A	123.0
H3A—C3—H3B	108.3	C13—C14—C15	129.5 (3)
C5—C4—O2	127.7 (3)	C13—C14—S1	110.1 (3)
C5—C4—C2	121.7 (3)	C15—C14—S1	120.4 (3)
O2—C4—C2	110.5 (3)	C16—C15—C14	128.6 (3)
C4—C5—C6	117.3 (3)	C16—C15—S2	110.4 (2)
C4—C5—H5A	121.3	C14—C15—S2	121.0 (3)
C6—C5—H5A	121.3	C17—C16—C15	109.2 (3)
C7—C6—C5	121.6 (3)	C17—C16—H16A	125.4
C7—C6—H6A	119.2	C15—C16—H16A	125.4
C5—C6—H6A	119.2	C18—C17—C16	115.4 (4)
C6—C7—C1	119.6 (3)	C18—C17—H17A	122.3
C6—C7—C8	123.5 (3)	C16—C17—H17A	122.3
C1—C7—C8	116.9 (3)	C17—C18—S2	112.1 (3)
O3—C8—C9	120.5 (3)	C17—C18—H18A	123.9
O3—C8—C7	119.9 (3)	S2—C18—H18A	123.9
C9—C8—C7	119.6 (3)
C7—C1—C2—C4	0.2 (5)	C7—C8—C9—C10	177.2 (3)
C7—C1—C2—O1	−179.5 (3)	C8—C9—C10—C11	178.5 (3)
C3—O1—C2—C1	179.0 (4)	C9—C10—C11—C12	−0.8 (6)
C3—O1—C2—C4	−0.6 (4)	C9—C10—C11—S1	−179.8 (3)
C2—O1—C3—O2	0.5 (4)	C14—S1—C11—C12	−0.3 (3)
C4—O2—C3—O1	−0.2 (4)	C14—S1—C11—C10	178.8 (3)
C3—O2—C4—C5	−179.0 (4)	C10—C11—C12—C13	−178.6 (3)
C3—O2—C4—C2	−0.2 (4)	S1—C11—C12—C13	0.4 (4)
C1—C2—C4—C5	−0.2 (6)	C11—C12—C13—C14	−0.3 (5)
O1—C2—C4—C5	179.5 (3)	C12—C13—C14—C15	−179.5 (3)
C1—C2—C4—O2	−179.2 (3)	C12—C13—C14—S1	0.1 (4)
O1—C2—C4—O2	0.5 (4)	C11—S1—C14—C13	0.1 (3)
O2—C4—C5—C6	178.7 (3)	C11—S1—C14—C15	179.8 (3)
C2—C4—C5—C6	0.0 (6)	C13—C14—C15—C16	176.6 (3)
C4—C5—C6—C7	0.3 (6)	S1—C14—C15—C16	−3.0 (5)
C5—C6—C7—C1	−0.4 (5)	C13—C14—C15—S2	−3.2 (5)
C5—C6—C7—C8	178.7 (3)	S1—C14—C15—S2	177.20 (19)
C2—C1—C7—C6	0.1 (5)	C18—S2—C15—C16	−1.2 (3)
C2—C1—C7—C8	−179.0 (3)	C18—S2—C15—C14	178.6 (3)
C6—C7—C8—O3	−176.3 (3)	C14—C15—C16—C17	−178.2 (3)
C1—C7—C8—O3	2.9 (5)	S2—C15—C16—C17	1.6 (4)
C6—C7—C8—C9	3.1 (5)	C15—C16—C17—C18	−1.4 (5)
C1—C7—C8—C9	−177.8 (3)	C16—C17—C18—S2	0.5 (5)
O3—C8—C9—C10	−3.5 (5)	C15—S2—C18—C17	0.4 (4)

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the S2/C15–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···Cg^i	0.97	2.74	3.472 (5)	132

Symmetry code: (i) −x+1, y−1/2, −z+1/2.