(2E,2′E)-1,1′-(1,4-Phenyl­ene)bis­[3-(3-chloro­phen­yl)prop-2-en-1-one]

The title bis-chalcone compound, C₂₄H₁₆Cl₂O₂, crystallizes with one half-mol­ecule in the asymmetric unit. The mol­ecule has crystallographic inversion symmetry and lies about an inversion centre at the centroid of the central benzene ring. The olefinic double bonds adopt E configurations. The s-trans conformation of the central C—C bond of the enone group is confirmed by a C—C—C=C torsion angle of −162.88 (17)°.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.056
• wR factor = 0.166
• Data-to-parameter ratio = 28.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      9.308 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.049 Check

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         14 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         13 Note

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   1 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: CrystalClear SM-Expert (Rigaku, 2011); cell refinement: CrystalClear SM-Expert (Rigaku, 2011); data reduction: CrystalClear SM-Expert (Rigaku, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: Mercury (Macrae et al., 2008).

(2E,2'E)-1,1'-(1,4-Phenylene)bis[3-(3-chlorophenyl)prop-2-en-1-one]

Crystal data

C24H16Cl2O2	F(000) = 420
Mr = 407.27	Dx = 1.423 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2542 reflections
a = 22.6336 (13) Å	θ = 2.7–33.3°
b = 7.0895 (4) Å	µ = 0.36 mm^−1
c = 5.9515 (3) Å	T = 294 K
β = 95.485 (2)°	Rectangle, white
V = 950.61 (9) Å^3	0.44 × 0.26 × 0.14 mm
Z = 2

Data collection

Rigaku Saturn724+ diffractometer	3656 independent reflections
Radiation source: fine-focus sealed tube	2542 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 18.4 pixels mm^-1	θmax = 33.3°, θmin = 2.7°
profile data from ω–scans	h = −34→34
Absorption correction: multi-scan (NUMABS; Rigaku, 1999)	k = −10→10
Tmin = 0.859, Tmax = 0.951	l = −9→9
27758 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.166	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0803P)^2 + 0.2606P] where P = (Fo^2 + 2Fc^2)/3
3656 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2sigma(F²) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
Cl1	0.04854 (2)	0.08183 (9)	0.31155 (9)	0.0694 (2)
O1	0.36614 (6)	0.0056 (3)	0.7913 (2)	0.0676 (6)
C1	0.16738 (6)	0.0708 (2)	0.3479 (2)	0.0351 (4)
C2	0.11601 (6)	0.0359 (2)	0.2094 (3)	0.0404 (4)
C3	0.11768 (7)	−0.0401 (2)	−0.0040 (3)	0.0447 (5)
C4	0.17253 (8)	−0.0790 (2)	−0.0789 (3)	0.0428 (5)
C5	0.22454 (7)	−0.0476 (2)	0.0578 (3)	0.0399 (4)
C6	0.22246 (6)	0.0251 (2)	0.2750 (2)	0.0343 (4)
C7	0.27480 (6)	0.0426 (2)	0.4386 (3)	0.0390 (4)
C8	0.32993 (6)	−0.0063 (3)	0.4068 (3)	0.0446 (5)
C9	0.37737 (6)	−0.0004 (3)	0.5956 (3)	0.0427 (4)
C10	0.44036 (6)	−0.0027 (2)	0.5403 (2)	0.0368 (4)
C11	0.45674 (6)	0.0564 (2)	0.3326 (3)	0.0399 (4)
C12	0.51588 (6)	0.0598 (2)	0.2924 (3)	0.0402 (4)
H1A	0.16530	0.12460	0.48940	0.0420*
H3A	0.08280	−0.06450	−0.09520	0.0540*
H4A	0.17440	−0.12700	−0.22350	0.0510*
H5A	0.26100	−0.07490	0.00500	0.0480*
H7A	0.26880	0.09300	0.57880	0.0470*
H8A	0.33880	−0.04460	0.26450	0.0540*
H11A	0.42780	0.09370	0.22000	0.0480*
H12A	0.52660	0.10040	0.15330	0.0480*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0279 (2)	0.1097 (5)	0.0716 (3)	0.0012 (2)	0.0101 (2)	−0.0044 (3)
O1	0.0364 (6)	0.1204 (14)	0.0466 (7)	0.0026 (7)	0.0066 (5)	0.0003 (8)
C1	0.0278 (6)	0.0424 (7)	0.0354 (6)	0.0011 (5)	0.0044 (5)	−0.0001 (5)
C2	0.0273 (6)	0.0482 (8)	0.0456 (8)	−0.0009 (5)	0.0038 (5)	0.0042 (6)
C3	0.0387 (8)	0.0496 (9)	0.0440 (8)	−0.0044 (6)	−0.0055 (6)	0.0008 (6)
C4	0.0496 (9)	0.0444 (8)	0.0340 (7)	0.0013 (6)	0.0014 (6)	−0.0025 (6)
C5	0.0364 (7)	0.0446 (8)	0.0396 (7)	0.0032 (6)	0.0082 (5)	−0.0006 (6)
C6	0.0280 (6)	0.0378 (7)	0.0371 (6)	−0.0001 (5)	0.0035 (5)	0.0012 (5)
C7	0.0289 (6)	0.0471 (8)	0.0407 (7)	0.0004 (5)	0.0023 (5)	−0.0023 (6)
C8	0.0275 (6)	0.0599 (10)	0.0463 (8)	0.0002 (6)	0.0025 (5)	−0.0070 (7)
C9	0.0271 (6)	0.0542 (9)	0.0467 (8)	−0.0004 (6)	0.0029 (5)	−0.0019 (7)
C10	0.0249 (6)	0.0423 (7)	0.0425 (7)	0.0000 (5)	0.0001 (5)	−0.0021 (6)
C11	0.0276 (6)	0.0482 (8)	0.0426 (7)	0.0025 (5)	−0.0035 (5)	0.0046 (6)
C12	0.0312 (6)	0.0505 (8)	0.0385 (7)	−0.0006 (6)	0.0010 (5)	0.0028 (6)

Geometric parameters (Å, º)

Cl1—C2	1.7277 (15)	C10—C11	1.389 (2)
O1—C9	1.216 (2)	C10—C12^i	1.396 (2)
C1—C2	1.382 (2)	C11—C12	1.382 (2)
C1—C6	1.3967 (19)	C1—H1A	0.9300
C2—C3	1.384 (2)	C3—H3A	0.9300
C3—C4	1.386 (2)	C4—H4A	0.9300
C4—C5	1.384 (2)	C5—H5A	0.9300
C5—C6	1.397 (2)	C7—H7A	0.9300
C6—C7	1.465 (2)	C8—H8A	0.9300
C7—C8	1.326 (2)	C11—H11A	0.9300
C8—C9	1.479 (2)	C12—H12A	0.9300
C9—C10	1.4936 (19)
C2—C1—C6	119.89 (12)	C10—C11—C12	120.31 (15)
Cl1—C2—C1	118.55 (12)	C10^i—C12—C11	120.29 (15)
Cl1—C2—C3	119.94 (12)	C2—C1—H1A	120.00
C1—C2—C3	121.47 (13)	C6—C1—H1A	120.00
C2—C3—C4	118.46 (15)	C2—C3—H3A	121.00
C3—C4—C5	121.11 (16)	C4—C3—H3A	121.00
C4—C5—C6	120.11 (15)	C3—C4—H4A	119.00
C1—C6—C5	118.89 (12)	C5—C4—H4A	119.00
C1—C6—C7	117.58 (12)	C4—C5—H5A	120.00
C5—C6—C7	123.35 (13)	C6—C5—H5A	120.00
C6—C7—C8	126.53 (16)	C6—C7—H7A	117.00
C7—C8—C9	120.60 (16)	C8—C7—H7A	117.00
O1—C9—C8	121.71 (14)	C7—C8—H8A	120.00
O1—C9—C10	120.17 (14)	C9—C8—H8A	120.00
C8—C9—C10	118.12 (14)	C10—C11—H11A	120.00
C9—C10—C11	122.31 (13)	C12—C11—H11A	120.00
C9—C10—C12^i	118.24 (13)	C11—C12—H12A	120.00
C11—C10—C12^i	119.40 (13)	C10^i—C12—H12A	120.00
C6—C1—C2—Cl1	176.37 (11)	C6—C7—C8—C9	−173.15 (16)
C6—C1—C2—C3	−1.5 (2)	C7—C8—C9—O1	17.4 (3)
C2—C1—C6—C5	2.9 (2)	C7—C8—C9—C10	−162.88 (17)
C2—C1—C6—C7	−172.42 (13)	O1—C9—C10—C11	−156.71 (19)
Cl1—C2—C3—C4	−178.63 (12)	O1—C9—C10—C12^i	20.8 (3)
C1—C2—C3—C4	−0.8 (2)	C8—C9—C10—C11	23.5 (3)
C2—C3—C4—C5	1.7 (2)	C8—C9—C10—C12^i	−158.96 (16)
C3—C4—C5—C6	−0.2 (2)	C9—C10—C11—C12	177.09 (15)
C4—C5—C6—C1	−2.1 (2)	C12^i—C10—C11—C12	−0.4 (2)
C4—C5—C6—C7	172.97 (14)	C9—C10—C12^i—C11^i	−177.19 (15)
C1—C6—C7—C8	174.96 (17)	C11—C10—C12^i—C11^i	0.4 (2)
C5—C6—C7—C8	−0.1 (2)	C10—C11—C12—C10^i	0.4 (2)

Symmetry code: (i) −x+1, −y, −z+1.