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

The title bis-chalcone compound, C₂₄H₁₆F₂O₂, crystallizes with one half-mol­ecule in the asymmetric unit. The mol­ecule lies about an inversion centre at the centroid of the central benzene ring. The olefinic double bonds adopt E conformations. In the crystal, C—H...O hydrogen bonds form sheets of mol­ecules in the ac plane and C—H...F hydrogen bonds form zigzag chains along the a-axis direction. These combine to generate a three-dimensional network of mol­ecules stacked along the c-axis direction.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.069
• wR factor = 0.203
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      8.583 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          7 Report

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
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.12 Report
PLAT093_ALERT_1_G No s.u.'s on H-positions, Refinement Reported as      mixed Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          6 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 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
   7 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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)-3,3'-(1,4-Phenylene)bis[1-(4-fluorophenyl)prop-2-en-1-one]

Crystal data

C24H16F2O2	F(000) = 388
Mr = 374.37	Dx = 1.422 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1379 reflections
a = 20.405 (6) Å	θ = 2.0–27.4°
b = 3.8237 (11) Å	µ = 0.10 mm^−1
c = 11.233 (3) Å	T = 100 K
β = 93.989 (5)°	Rectangle, white
V = 874.3 (4) Å^3	0.22 × 0.15 × 0.13 mm
Z = 2

Data collection

Rigaku Saturn724+ diffractometer	1963 independent reflections
Radiation source: fine-focus sealed tube	1379 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 18.4 pixels mm^-1	θmax = 27.4°, θmin = 2.0°
profile data from ω–scans	h = −25→26
Absorption correction: multi-scan (NUMABS; Rigaku, 1999)	k = −4→4
Tmin = 0.977, Tmax = 0.987	l = −14→14
6328 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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.203	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.1169P)^2 + 0.1724P] where P = (Fo^2 + 2Fc^2)/3
1963 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.37 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
F1	0.02041 (7)	0.3368 (4)	0.88439 (14)	0.0309 (5)
O1	0.29100 (8)	0.6037 (5)	0.66903 (15)	0.0296 (6)
C1	0.16568 (12)	0.4078 (6)	0.7220 (2)	0.0217 (7)
C2	0.10182 (12)	0.3342 (6)	0.7470 (2)	0.0239 (8)
C3	0.08291 (11)	0.4157 (6)	0.8586 (2)	0.0223 (7)
C4	0.12399 (11)	0.5737 (6)	0.9452 (2)	0.0227 (8)
C5	0.18808 (11)	0.6453 (6)	0.9197 (2)	0.0215 (7)
C6	0.20983 (11)	0.5648 (6)	0.8074 (2)	0.0195 (7)
C7	0.27745 (12)	0.6434 (6)	0.7722 (2)	0.0218 (7)
C8	0.32763 (12)	0.7663 (6)	0.8654 (2)	0.0213 (7)
C9	0.39052 (11)	0.7978 (6)	0.8397 (2)	0.0204 (7)
C10	0.44537 (11)	0.9062 (6)	0.9229 (2)	0.0203 (7)
C11	0.43665 (12)	1.0668 (6)	1.0322 (2)	0.0219 (7)
C12	0.50979 (12)	0.8414 (6)	0.8921 (2)	0.0207 (7)
H1A	0.18000	0.35110	0.64570	0.0260*
H2A	0.07190	0.23040	0.68880	0.0290*
H4A	0.10870	0.63200	1.02070	0.0270*
H5A	0.21740	0.74970	0.97870	0.0260*
H8A	0.31510	0.82230	0.94300	0.0260*
H9A	0.40050	0.74510	0.76030	0.0250*
H11A	0.39350	1.11350	1.05480	0.0260*
H12A	0.51670	0.73270	0.81800	0.0250*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0202 (8)	0.0400 (9)	0.0327 (9)	−0.0027 (6)	0.0033 (6)	0.0003 (7)
O1	0.0271 (10)	0.0471 (12)	0.0147 (9)	−0.0049 (8)	0.0016 (7)	−0.0024 (8)
C1	0.0273 (13)	0.0205 (12)	0.0170 (12)	0.0007 (9)	−0.0015 (9)	0.0007 (9)
C2	0.0233 (13)	0.0247 (13)	0.0225 (13)	−0.0004 (10)	−0.0068 (9)	−0.0015 (10)
C3	0.0203 (12)	0.0194 (12)	0.0271 (14)	0.0010 (9)	0.0004 (9)	0.0044 (9)
C4	0.0243 (13)	0.0256 (14)	0.0180 (12)	0.0020 (10)	0.0008 (9)	0.0004 (9)
C5	0.0249 (13)	0.0230 (12)	0.0161 (12)	0.0004 (10)	−0.0013 (9)	0.0012 (9)
C6	0.0236 (12)	0.0180 (12)	0.0163 (12)	0.0009 (9)	−0.0020 (9)	0.0010 (8)
C7	0.0264 (13)	0.0226 (12)	0.0159 (12)	0.0002 (10)	−0.0019 (9)	0.0006 (9)
C8	0.0224 (12)	0.0253 (13)	0.0157 (12)	−0.0008 (9)	−0.0016 (9)	−0.0006 (9)
C9	0.0226 (13)	0.0241 (13)	0.0144 (12)	−0.0013 (9)	−0.0001 (9)	0.0003 (9)
C10	0.0213 (12)	0.0217 (12)	0.0175 (12)	−0.0029 (9)	−0.0017 (9)	0.0036 (9)
C11	0.0226 (12)	0.0238 (13)	0.0191 (12)	−0.0008 (9)	0.0007 (9)	0.0025 (9)
C12	0.0258 (13)	0.0227 (12)	0.0136 (12)	−0.0013 (9)	0.0009 (9)	0.0000 (9)

Geometric parameters (Å, º)

F1—C3	1.361 (3)	C10—C11	1.395 (3)
O1—C7	1.220 (3)	C10—C12	1.404 (3)
C1—C2	1.381 (3)	C11—C12^i	1.383 (3)
C1—C6	1.404 (3)	C1—H1A	0.9500
C2—C3	1.373 (3)	C2—H2A	0.9500
C3—C4	1.379 (3)	C4—H4A	0.9500
C4—C5	1.385 (3)	C5—H5A	0.9500
C5—C6	1.400 (3)	C8—H8A	0.9500
C6—C7	1.492 (3)	C9—H9A	0.9500
C7—C8	1.489 (3)	C11—H11A	0.9500
C8—C9	1.340 (3)	C12—H12A	0.9500
C9—C10	1.467 (3)
C2—C1—C6	121.2 (2)	C10—C11—C12^i	120.6 (2)
C1—C2—C3	117.9 (2)	C10—C12—C11^i	121.1 (2)
F1—C3—C2	118.1 (2)	C2—C1—H1A	119.00
F1—C3—C4	118.7 (2)	C6—C1—H1A	119.00
C2—C3—C4	123.2 (2)	C1—C2—H2A	121.00
C3—C4—C5	118.5 (2)	C3—C2—H2A	121.00
C4—C5—C6	120.4 (2)	C3—C4—H4A	121.00
C1—C6—C5	118.7 (2)	C5—C4—H4A	121.00
C1—C6—C7	117.8 (2)	C4—C5—H5A	120.00
C5—C6—C7	123.5 (2)	C6—C5—H5A	120.00
O1—C7—C6	120.1 (2)	C7—C8—H8A	120.00
O1—C7—C8	121.2 (2)	C9—C8—H8A	120.00
C6—C7—C8	118.7 (2)	C8—C9—H9A	117.00
C7—C8—C9	119.9 (2)	C10—C9—H9A	117.00
C8—C9—C10	126.0 (2)	C10—C11—H11A	120.00
C9—C10—C11	123.1 (2)	C12^i—C11—H11A	120.00
C9—C10—C12	118.6 (2)	C10—C12—H12A	119.00
C11—C10—C12	118.3 (2)	C11^i—C12—H12A	119.00
C6—C1—C2—C3	−0.7 (3)	C5—C6—C7—O1	−171.6 (2)
C2—C1—C6—C5	0.3 (3)	C5—C6—C7—C8	9.1 (3)
C2—C1—C6—C7	−178.6 (2)	O1—C7—C8—C9	−7.5 (4)
C1—C2—C3—F1	−178.6 (2)	C6—C7—C8—C9	171.9 (2)
C1—C2—C3—C4	1.5 (4)	C7—C8—C9—C10	−178.3 (2)
F1—C3—C4—C5	178.3 (2)	C8—C9—C10—C11	−15.2 (4)
C2—C3—C4—C5	−1.8 (4)	C8—C9—C10—C12	163.9 (2)
C3—C4—C5—C6	1.3 (3)	C9—C10—C11—C12^i	179.0 (2)
C4—C5—C6—C1	−0.6 (3)	C12—C10—C11—C12^i	−0.1 (3)
C4—C5—C6—C7	178.2 (2)	C9—C10—C12—C11^i	−179.1 (2)
C1—C6—C7—O1	7.2 (3)	C11—C10—C12—C11^i	0.1 (3)
C1—C6—C7—C8	−172.1 (2)	C10—C11—C12^i—C10^i	0.1 (3)

Symmetry code: (i) −x+1, −y+2, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···F1^ii	0.95	2.50	3.392 (3)	155
C5—H5A···O1^iii	0.95	2.59	3.515 (3)	166
C8—H8A···O1^iii	0.95	2.63	3.577 (3)	171

Symmetry codes: (ii) −x, y−1/2, −z+3/2; (iii) x, −y+3/2, z+1/2.