Crystal structure and Hirshfeld surface analysis of a conformationally unsymmetrical bis­chalcone: (1E,4E)-1,5-bis­(4-bromo­phen­yl)penta-1,4-dien-3-one

Arif Tawfeeq, N.; Kwong, H.C.; Mohamed Tahir, M.I.; Ravoof, T.B.S.A.

doi:10.1107/S2056989019006480

Crystal structure and Hirshfeld surface analysis of a conformationally unsymmetrical bischalcone: (1E,4E)-1,5-bis(4-bromophenyl)penta-1,4-dien-3-one

N. Arif Tawfeeq, H. C. Kwong, M. I. Mohamed Tahir and T. B. S. A. Ravoof

The title bischalcone shows s-trans and s-cis conformations for its C=C—C=O bonds.

Keywords: crystal structure; bischalcone; pentadienone bridge; C—H

π interactions; Hirshfeld surface analysis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019006480/hb7821sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989019006480/hb7821Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019006480/hb7821Isup3.cml Supplementary material

CCDC reference: 1914420

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R factor = 0.022
wR factor = 0.056
Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.214 Check

Alert level G
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        91% Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT953_ALERT_1_G Reported (CIF) and Actual (FCF) Hmax Differ by .          1 Units
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          9 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXL2013 (Sheldrick, 2015) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015) and PLATON (Spek, 2009).

(1E,4E)-1,5-Bis(4-bromophenyl)penta-1,4-dien-3-one top

Crystal data top

C₁₇H₁₂Br₂O	F(000) = 768
M_r = 392.09	D_x = 1.836 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 17.5920 (2) Å	Cell parameters from 11112 reflections
b = 14.0777 (3) Å	θ = 4–76°
c = 5.7956 (1) Å	µ = 7.17 mm⁻¹
β = 98.742 (1)°	T = 100 K
V = 1418.63 (4) Å³	Block, yellow
Z = 4	0.12 × 0.06 × 0.03 mm

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2372 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω scans	θ_max = 67.1°, θ_min = 4.0°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −21→18
T_min = 0.64, T_max = 0.79	k = −16→16
17456 measured reflections	l = −6→6
2524 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.022	H-atom parameters constrained
wR(F²) = 0.056	w = 1/[σ²(F_o²) + (0.0179P)² + 1.9865P] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max = 0.003
2524 reflections	Δρ_max = 0.42 e Å⁻³
181 parameters	Δρ_min = −0.40 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.14690 (2)	0.38377 (2)	−0.19437 (5)	0.02381 (9)
Br2	1.00765 (2)	0.35118 (2)	0.21721 (5)	0.02140 (9)
O1	0.58973 (11)	0.35870 (14)	0.9112 (3)	0.0230 (4)
C1	0.33281 (15)	0.33927 (19)	0.3232 (4)	0.0190 (5)
H1A	0.341393	0.310601	0.469408	0.023*
C2	0.25910 (14)	0.34239 (19)	0.2021 (4)	0.0193 (5)
H2A	0.218193	0.316997	0.266165	0.023*
C3	0.24703 (14)	0.38441 (19)	−0.0186 (4)	0.0192 (5)
C4	0.30666 (15)	0.42466 (18)	−0.1141 (4)	0.0193 (5)
H4A	0.297492	0.453469	−0.260084	0.023*
C5	0.38031 (14)	0.42161 (18)	0.0103 (4)	0.0187 (5)
H5A	0.420665	0.448675	−0.053317	0.022*
C6	0.39517 (14)	0.37826 (18)	0.2313 (4)	0.0176 (5)
C7	0.47449 (15)	0.37678 (18)	0.3537 (4)	0.0187 (5)
H7A	0.512770	0.395031	0.268379	0.022*
C8	0.49705 (15)	0.35175 (18)	0.5758 (4)	0.0188 (5)
H8A	0.460021	0.328563	0.659851	0.023*
C9	0.57702 (15)	0.35856 (18)	0.6962 (4)	0.0194 (5)
C10	0.64033 (14)	0.36427 (18)	0.5544 (4)	0.0186 (5)
H10A	0.630488	0.349029	0.396510	0.022*
C11	0.71104 (14)	0.39078 (18)	0.6484 (4)	0.0169 (5)
H11A	0.717134	0.413278	0.800928	0.020*
C12	0.78029 (14)	0.38804 (18)	0.5353 (4)	0.0165 (5)
C13	0.77978 (14)	0.34717 (18)	0.3144 (4)	0.0166 (5)
H13A	0.733445	0.327076	0.229449	0.020*
C14	0.84699 (14)	0.33627 (18)	0.2209 (4)	0.0174 (5)
H14A	0.846014	0.308769	0.074547	0.021*
C15	0.91600 (14)	0.36684 (18)	0.3479 (4)	0.0180 (5)
C16	0.91859 (14)	0.40921 (18)	0.5654 (4)	0.0180 (5)
H16A	0.964994	0.430278	0.647991	0.022*
C17	0.85050 (14)	0.41952 (19)	0.6572 (4)	0.0171 (5)
H17A	0.851669	0.447926	0.802583	0.021*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.01735 (14)	0.02515 (16)	0.02724 (15)	0.00374 (11)	−0.00210 (10)	0.00155 (11)
Br2	0.01568 (14)	0.02560 (16)	0.02334 (15)	−0.00101 (10)	0.00433 (10)	−0.00280 (11)
O1	0.0235 (9)	0.0274 (11)	0.0181 (9)	−0.0039 (8)	0.0034 (7)	0.0004 (7)
C1	0.0212 (13)	0.0189 (13)	0.0173 (12)	0.0008 (10)	0.0041 (10)	−0.0004 (10)
C2	0.0175 (12)	0.0185 (13)	0.0225 (13)	−0.0010 (10)	0.0054 (10)	0.0002 (10)
C3	0.0182 (12)	0.0179 (13)	0.0209 (12)	0.0038 (10)	0.0009 (10)	−0.0009 (10)
C4	0.0252 (13)	0.0153 (13)	0.0174 (12)	0.0039 (11)	0.0040 (10)	−0.0002 (10)
C5	0.0203 (12)	0.0163 (13)	0.0208 (12)	−0.0001 (10)	0.0074 (10)	−0.0009 (10)
C6	0.0200 (13)	0.0141 (12)	0.0192 (12)	0.0006 (10)	0.0048 (10)	−0.0035 (10)
C7	0.0183 (12)	0.0165 (13)	0.0225 (12)	−0.0013 (10)	0.0067 (10)	−0.0013 (10)
C8	0.0183 (12)	0.0169 (13)	0.0220 (13)	−0.0023 (10)	0.0054 (10)	−0.0026 (10)
C9	0.0218 (13)	0.0157 (13)	0.0213 (13)	0.0002 (10)	0.0050 (10)	−0.0005 (10)
C10	0.0194 (13)	0.0193 (14)	0.0168 (12)	0.0009 (10)	0.0022 (10)	−0.0008 (10)
C11	0.0190 (12)	0.0144 (13)	0.0171 (11)	0.0020 (10)	0.0022 (9)	0.0001 (9)
C12	0.0170 (12)	0.0147 (12)	0.0175 (12)	0.0007 (10)	0.0014 (9)	0.0031 (10)
C13	0.0151 (12)	0.0175 (13)	0.0157 (11)	−0.0007 (10)	−0.0022 (9)	0.0009 (9)
C14	0.0201 (12)	0.0166 (13)	0.0147 (11)	0.0000 (10)	0.0005 (10)	−0.0002 (10)
C15	0.0177 (12)	0.0179 (13)	0.0187 (12)	0.0021 (10)	0.0034 (10)	0.0034 (10)
C16	0.0166 (12)	0.0188 (13)	0.0172 (12)	−0.0013 (10)	−0.0019 (9)	0.0005 (10)
C17	0.0195 (12)	0.0173 (13)	0.0137 (11)	−0.0015 (10)	−0.0007 (9)	0.0003 (10)

Geometric parameters (Å, º) top

Br1—C3	1.896 (3)	C8—H8A	0.9300
Br2—C15	1.895 (2)	C9—C10	1.484 (4)
O1—C9	1.232 (3)	C10—C11	1.333 (4)
C1—C2	1.378 (4)	C10—H10A	0.9300
C1—C6	1.402 (4)	C11—C12	1.469 (3)
C1—H1A	0.9300	C11—H11A	0.9300
C2—C3	1.396 (4)	C12—C17	1.399 (3)
C2—H2A	0.9300	C12—C13	1.402 (3)
C3—C4	1.380 (4)	C13—C14	1.382 (4)
C4—C5	1.384 (4)	C13—H13A	0.9300
C4—H4A	0.9300	C14—C15	1.389 (4)
C5—C6	1.407 (4)	C14—H14A	0.9300
C5—H5A	0.9300	C15—C16	1.389 (4)
C6—C7	1.466 (4)	C16—C17	1.390 (4)
C7—C8	1.336 (4)	C16—H16A	0.9300
C7—H7A	0.9300	C17—H17A	0.9300
C8—C9	1.475 (4)

C2—C1—C6	121.6 (2)	C8—C9—C10	118.9 (2)
C2—C1—H1A	119.2	C11—C10—C9	121.4 (2)
C6—C1—H1A	119.2	C11—C10—H10A	119.3
C1—C2—C3	118.7 (2)	C9—C10—H10A	119.3
C1—C2—H2A	120.6	C10—C11—C12	126.6 (2)
C3—C2—H2A	120.6	C10—C11—H11A	116.7
C4—C3—C2	121.5 (2)	C12—C11—H11A	116.7
C4—C3—Br1	119.17 (19)	C17—C12—C13	118.3 (2)
C2—C3—Br1	119.33 (19)	C17—C12—C11	119.7 (2)
C3—C4—C5	119.1 (2)	C13—C12—C11	121.8 (2)
C3—C4—H4A	120.4	C14—C13—C12	121.1 (2)
C5—C4—H4A	120.4	C14—C13—H13A	119.5
C4—C5—C6	121.2 (2)	C12—C13—H13A	119.5
C4—C5—H5A	119.4	C13—C14—C15	119.3 (2)
C6—C5—H5A	119.4	C13—C14—H14A	120.4
C1—C6—C5	117.9 (2)	C15—C14—H14A	120.4
C1—C6—C7	123.6 (2)	C16—C15—C14	121.3 (2)
C5—C6—C7	118.5 (2)	C16—C15—Br2	119.99 (19)
C8—C7—C6	126.3 (2)	C14—C15—Br2	118.71 (19)
C8—C7—H7A	116.9	C15—C16—C17	118.7 (2)
C6—C7—H7A	116.9	C15—C16—H16A	120.6
C7—C8—C9	124.1 (2)	C17—C16—H16A	120.6
C7—C8—H8A	117.9	C16—C17—C12	121.3 (2)
C9—C8—H8A	117.9	C16—C17—H17A	119.3
O1—C9—C8	119.5 (2)	C12—C17—H17A	119.3
O1—C9—C10	121.6 (2)

C6—C1—C2—C3	0.9 (4)	O1—C9—C10—C11	−15.2 (4)
C1—C2—C3—C4	−1.7 (4)	C8—C9—C10—C11	165.4 (2)
C1—C2—C3—Br1	176.9 (2)	C9—C10—C11—C12	171.9 (2)
C2—C3—C4—C5	1.2 (4)	C10—C11—C12—C17	179.3 (3)
Br1—C3—C4—C5	−177.34 (19)	C10—C11—C12—C13	−6.2 (4)
C3—C4—C5—C6	0.0 (4)	C17—C12—C13—C14	1.4 (4)
C2—C1—C6—C5	0.3 (4)	C11—C12—C13—C14	−173.2 (2)
C2—C1—C6—C7	179.9 (2)	C12—C13—C14—C15	−0.3 (4)
C4—C5—C6—C1	−0.8 (4)	C13—C14—C15—C16	−0.8 (4)
C4—C5—C6—C7	179.6 (2)	C13—C14—C15—Br2	179.91 (19)
C1—C6—C7—C8	−10.2 (4)	C14—C15—C16—C17	0.9 (4)
C5—C6—C7—C8	169.4 (3)	Br2—C15—C16—C17	−179.82 (19)
C6—C7—C8—C9	−175.0 (2)	C15—C16—C17—C12	0.1 (4)
C7—C8—C9—O1	160.7 (3)	C13—C12—C17—C16	−1.3 (4)
C7—C8—C9—C10	−19.8 (4)	C11—C12—C17—C16	173.4 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C16 and C12–C17 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Cg1ⁱ	0.93	2.86	3.539 (3)	131
C14—H14A···Cg2ⁱⁱ	0.93	2.74	3.428 (3)	131

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

Torsion angles τ1, τ2, τ3 and τ4 (°) top

Compound	R₁	R₂	τ₁	τ₂	τ₃	τ₄
Symmetrical
AMEXUN (Mark et al., 2016)	4-(benzyloxy)-3-methoxyphenyl	4-(benzyloxy)-3-methoxyphenyl	27.4	19.3	20.4	22.5
COGNOD01 (Rawal et al., 2016)	4-(diethylamino)phenyl	4-(diethylamino)phenyl	1.2, 4.0	11.0, 4.2	1.3, 2.9	0.7, 1.6
DUMWIS (Fun et al., 2010)	2,4,5-trimethoxyphenyl	2,4,5-trimethoxyphenyl	11.6, 0.4, 11.8	0.7, 4.0, 5.5	3.0, 8.2, 6.0	9.8, 2.9, 3.7
EDUSEE (Rawal et al., 2016)	4-(diethylamino)phenyl	4-benzonitrile	15.6, 5.9	0.1, 6.4	8.1, 7.7	3.7, 3.2
GOLGOD (Shan et al., 1999)	4-methoxyphenyl	4-methoxyphenyl	3.2	153.4	152.9	2.7
GOLGOD02 (Harrison et al., 2006)	4-methoxyphenyl	4-methoxyphenyl	2.4	152.2	152.2	2.4
HIDMIQ (Zhou et al., 1999)	2-methoxyphenyl	2-methoxyphenyl	0.2	1.4	1.2	8.8
HUDLEY (Feng et al., 2009)	2,4-dimethylpheny	2,4-dimethylpheny	26.1	3.1	1.1	24.6
KOFCEO (Arshad et al., 2008)	4-methylphenyl	4-methylphenyl	16.6	4.0	13	180
LEJNOE (Butcher et al., 2006)	4-chlorophenyl	4-chlorophenyl	17.8	9.8	9.8	17.8
LESGAT (Park et al., 2013)	2-(trifluoromethyl)phenyl	2-(trifluoromethyl)phenyl	0.5	0.3	2.9	13.7
SAFZOQ (Samshuddin et al., 2012)	3-nitropheny	phenyl	6.1	11.3	21.9	10.4
SIMTUE (Nizam Mohideen et al., 2007)	2-chlorophenyl	2-chlorophenyl	8.8	3.4	0.9	0.5
UPAWEO (Huang et al., 2011)	2,6-difluorophenyl	2,6-difluorophenyl	2.3	4.4	0.8	178
UPAWEO01 (Schwarzer & Weber, 2014a)	2,6-difluorophenyl	2,6-difluorophenyl	2.3	4.4	0.8	0.5
WACXON (Hubig et al., 1992)	o-tolyl	o-tolyl	10.3	1.1	2.8	1.5
XOHVOH (Schwarzer & Weber, 2014b)	pentafluorophenyl	pentafluorophenyl	3.0, 7.9	1.0, 5.7	1.6, 3.4	5.7, 2.3
XOHVUN (Schwarzer & Weber, 2014b)	pentafluorophenyl	phenyl	5.6	2.4	3.3	7.8

Unsymmetrical
(I)	4-bromophenyl	4-bromophenyl	10.2	160.7	15.2	6.2
IFAQAJ (Kapdi et al., 2013)	3,5-dimethoxyphenyl	3,5-dimethoxyphenyl	5.4	173.1	0.6	3.2
LEJNOE01 (Maluleka & Mphahlele, 2017)	4-chlorophenyl	4-chlorophenyl	11.2	160.2	13.6	6.6
MESXEQ (Dravida et al., 2018)	2,6-dichlorophenyl	2,6-dichlorophenyl	46.8, 48.7, 51.8	175.3, 4.3, 178.7	7.5, 4.3, 15.5	32.7, 48.7, 51.8
QAJNOG (Ruanwas et al., 2011)	2,4,6-trimethoxyphenyl	2,4,6-trimethoxyphenyl	6.6, 0.5	176.8, 169.4	1.2, 0.5	3.7, 11.8
WIHBUL (Butcher et al., 2007a)	4-fluorophenyl	4-fluorophenyl	18.2, 18.7	169.0, 166.3	10.4, 8.8	21.8, 21.4
XIFTOW (Butcher et al., 2007b)	3,4-dimethoxyphenyl	3,4-dimethoxyphenyl	1.6, 1.6	162.8, 170.8	23.3, 23.7	3.1, 20.3
ZAPKIN (Chantrapromma et al., 2016)	4-ethoxyphenyl	4-ethoxyphenyl	17.2	168.4	17.1	13.8

Multiple sets of torsion angles are stated for compounds COGNOD01, DUMWIS, EDUSEE, XOHVOH, MESXEQ, QAJNOG, WIHBUL and XIFTOW because there is more than one independent molecule in their asymmetric units. A third molecule with full molecule disorder in compound WIHBUL was excluded from this table.

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Crystal structure and Hirshfeld surface analysis of a conformationally unsymmetrical bis­chalcone: (1E,4E)-1,5-bis­(4-bromo­phen­yl)penta-1,4-dien-3-one

Supporting information

Key indicators

checkCIF/PLATON results

Crystal structure and Hirshfeld surface analysis of a conformationally unsymmetrical bischalcone: (1E,4E)-1,5-bis(4-bromophenyl)penta-1,4-dien-3-one