1,5-Bis(4-chloro-phen-yl)-3-(4-methyl-phen-yl)pentane-1,5-dione.

In the title mol-ecule, C24H20Cl2O2, the central methyl-benzene ring forms dihedral angles of 42.47 (10) and 34.34 (10)° with the terminal 4-chloro-phenyl fragments. The dihedral angle between the chloro-benzene rings is 34.45 (11)°. A weak intra-molecular C-H⋯O inter-action generates an S(6) ring motif. The crystal packing exhibits weak C-H⋯O hydrogen bonds and C-H⋯π inter-actions.

Related literature

For the synthesis of 1,5-diketones, see: Yang et al. (2005 ▶); Hirsch & Bailey (1978 ▶). For the crystal structures of related compounds, see: Qiu et al. (2006 ▶); Insuasty et al. (2006 ▶); Jasinski et al. (2007 ▶); Huang et al. (2008 ▶); Lei & Bai (2009 ▶); Dutkiewicz et al. (2010 ▶); Fun et al. (2011 ▶). For the applications of delocalized π-systems, see: Burroughes et al. (1990 ▶); Smith et al. (2005 ▶); Li et al. (2004 ▶); Sariciftci et al. (1992 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C24H20Cl2O2

M = 411.30

Monoclinic,

a = 18.6794 (11) Å

b = 7.5477 (4) Å

c = 15.5196 (8) Å

β = 103.622 (5)°

V = 2126.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 296 K

0.51 × 0.42 × 0.37 mm

Data collection

Agilent Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.443, T max = 1.000

14252 measured reflections

4341 independent reflections

3735 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.146

S = 1.07

4341 reflections

255 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.37 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: DIRDIF2008 (Beurskens et al., 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL2013 and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813024355/jj2174sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813024355/jj2174Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813024355/jj2174Isup3.cdx

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813024355/jj2174Isup4.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C24H20Cl2O2	F(000) = 856
Mr = 411.30	Dx = 1.285 Mg m−3
Monoclinic, P21/c	Melting point: 327(2) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 18.6794 (11) Å	Cell parameters from 5569 reflections
b = 7.5477 (4) Å	θ = 3.3–75.4°
c = 15.5196 (8) Å	µ = 0.32 mm−1
β = 103.622 (5)°	T = 296 K
V = 2126.5 (2) Å3	Prism, colourless
Z = 4	0.51 × 0.42 × 0.37 mm

Agilent Xcalibur Ruby Gemini diffractometer	4341 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3735 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 10.5081 pixels mm-1	θmax = 26.5°, θmin = 2.2°
ω scans	h = −23→21
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −9→8
Tmin = 0.443, Tmax = 1.000	l = −19→15
14252 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.050	w = 1/[σ2(Fo2) + (0.0627P)2 + 0.5487P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.146	(Δ/σ)max = 0.001
S = 1.07	Δρmax = 0.33 e Å−3
4341 reflections	Δρmin = −0.37 e Å−3
255 parameters	Extinction correction: SHELXL2013 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0227 (17)

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 e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

	x	y	z	Uiso*/Ueq
Cl14	0.50733 (5)	0.76817 (14)	0.95387 (6)	0.1283 (4)
Cl54	0.08862 (5)	1.03187 (11)	0.11762 (5)	0.1154 (3)
O1	0.32422 (10)	0.76750 (19)	0.53035 (12)	0.0873 (6)
O5	0.27979 (11)	0.3043 (2)	0.26076 (12)	0.0939 (7)
C1	0.32982 (10)	0.6468 (3)	0.58359 (14)	0.0638 (6)
C2	0.29189 (10)	0.4711 (2)	0.55773 (13)	0.0621 (6)
C3	0.25188 (9)	0.4591 (2)	0.46011 (12)	0.0555 (5)
C4	0.30797 (10)	0.4435 (3)	0.40126 (13)	0.0647 (6)
C5	0.27264 (11)	0.4342 (3)	0.30405 (14)	0.0644 (6)
C11	0.37394 (9)	0.6711 (3)	0.67653 (14)	0.0626 (6)
C12	0.40855 (12)	0.8328 (3)	0.70082 (17)	0.0809 (8)
C13	0.44906 (13)	0.8624 (4)	0.7860 (2)	0.0933 (10)
C14	0.45523 (12)	0.7294 (4)	0.84725 (17)	0.0838 (9)
C15	0.42146 (13)	0.5692 (3)	0.82660 (16)	0.0813 (8)
C16	0.38072 (11)	0.5404 (3)	0.74081 (14)	0.0705 (7)
C31	0.19689 (9)	0.3081 (2)	0.44168 (11)	0.0525 (5)
C32	0.21576 (10)	0.1365 (2)	0.46994 (12)	0.0596 (5)
C33	0.16507 (11)	0.0008 (3)	0.45037 (13)	0.0649 (6)
C34	0.09424 (12)	0.0296 (3)	0.40097 (13)	0.0676 (6)
C35	0.07564 (11)	0.1993 (3)	0.37249 (15)	0.0754 (7)
C36	0.12561 (10)	0.3367 (3)	0.39251 (14)	0.0668 (6)
C37	0.04025 (16)	−0.1219 (4)	0.3772 (2)	0.1036 (10)
C51	0.22673 (10)	0.5860 (2)	0.25994 (12)	0.0591 (6)
C52	0.17530 (13)	0.5558 (3)	0.18151 (14)	0.0766 (8)
C53	0.13217 (14)	0.6916 (4)	0.13849 (15)	0.0844 (9)
C54	0.14217 (13)	0.8596 (3)	0.17322 (14)	0.0739 (7)
C55	0.19288 (12)	0.8948 (3)	0.25063 (14)	0.0701 (7)
C56	0.23502 (11)	0.7562 (2)	0.29495 (13)	0.0619 (6)
H2A	0.25663	0.45128	0.59369	0.0745*
H2B	0.32834	0.37735	0.57095	0.0745*
H3	0.22450	0.56978	0.44428	0.0666*
H4A	0.34075	0.54492	0.41221	0.0776*
H4B	0.33758	0.33800	0.41830	0.0776*
H12	0.40425	0.92255	0.65885	0.0970*
H13	0.47188	0.97108	0.80159	0.1118*
H15	0.42573	0.48107	0.86937	0.0975*
H16	0.35758	0.43174	0.72612	0.0846*
H32	0.26327	0.11248	0.50255	0.0714*
H33	0.17890	−0.11285	0.47092	0.0778*
H35	0.02834	0.22220	0.33896	0.0905*
H36	0.11120	0.45041	0.37267	0.0802*
H37A	0.01457	−0.13765	0.42342	0.1553*
H37B	0.06642	−0.22851	0.37049	0.1553*
H37C	0.00548	−0.09558	0.32250	0.1553*
H52	0.16976	0.44229	0.15749	0.0920*
H53	0.09667	0.66994	0.08653	0.1012*
H55	0.19902	1.00942	0.27314	0.0842*
H56	0.26892	0.77754	0.34828	0.0742*

	U11	U22	U33	U12	U13	U23
Cl14	0.1032 (5)	0.1647 (9)	0.1004 (5)	−0.0240 (5)	−0.0091 (4)	−0.0387 (5)
Cl54	0.1193 (6)	0.1104 (6)	0.1139 (6)	0.0419 (4)	0.0225 (4)	0.0407 (4)
O1	0.0932 (11)	0.0590 (8)	0.0993 (11)	−0.0099 (8)	0.0019 (9)	0.0133 (8)
O5	0.1211 (14)	0.0656 (9)	0.1022 (12)	0.0217 (9)	0.0405 (11)	−0.0103 (8)
C1	0.0529 (9)	0.0552 (10)	0.0820 (12)	0.0002 (8)	0.0131 (8)	0.0033 (9)
C2	0.0566 (10)	0.0565 (10)	0.0712 (11)	−0.0045 (8)	0.0112 (8)	0.0022 (8)
C3	0.0497 (8)	0.0505 (9)	0.0668 (10)	0.0040 (7)	0.0150 (7)	0.0062 (7)
C4	0.0532 (9)	0.0616 (10)	0.0823 (12)	0.0055 (8)	0.0222 (9)	0.0091 (9)
C5	0.0671 (11)	0.0552 (10)	0.0787 (12)	0.0025 (8)	0.0326 (9)	0.0011 (9)
C11	0.0463 (9)	0.0605 (10)	0.0822 (12)	−0.0050 (8)	0.0174 (8)	−0.0064 (9)
C12	0.0711 (13)	0.0719 (13)	0.1003 (16)	−0.0206 (10)	0.0214 (11)	−0.0078 (12)
C13	0.0734 (14)	0.0910 (17)	0.115 (2)	−0.0313 (13)	0.0215 (13)	−0.0300 (15)
C14	0.0568 (11)	0.1059 (18)	0.0862 (15)	−0.0097 (11)	0.0121 (10)	−0.0243 (14)
C15	0.0712 (13)	0.0886 (15)	0.0796 (14)	−0.0029 (11)	0.0088 (10)	−0.0025 (12)
C16	0.0611 (11)	0.0675 (12)	0.0801 (13)	−0.0088 (9)	0.0109 (9)	−0.0048 (10)
C31	0.0515 (8)	0.0530 (9)	0.0538 (9)	0.0018 (7)	0.0142 (7)	0.0021 (7)
C32	0.0578 (9)	0.0564 (9)	0.0618 (10)	0.0035 (8)	0.0088 (7)	0.0024 (8)
C33	0.0763 (12)	0.0512 (9)	0.0673 (11)	−0.0017 (8)	0.0174 (9)	0.0012 (8)
C34	0.0693 (11)	0.0680 (11)	0.0656 (11)	−0.0139 (9)	0.0161 (9)	−0.0065 (9)
C35	0.0532 (10)	0.0831 (14)	0.0836 (14)	−0.0055 (10)	0.0034 (9)	0.0072 (11)
C36	0.0554 (10)	0.0615 (10)	0.0802 (12)	0.0041 (8)	0.0094 (9)	0.0126 (9)
C37	0.0965 (18)	0.0865 (16)	0.120 (2)	−0.0326 (15)	0.0096 (15)	−0.0107 (15)
C51	0.0632 (10)	0.0577 (10)	0.0627 (10)	0.0011 (8)	0.0274 (8)	0.0007 (8)
C52	0.0894 (15)	0.0721 (13)	0.0706 (12)	0.0036 (11)	0.0232 (11)	−0.0134 (10)
C53	0.0842 (15)	0.1014 (17)	0.0645 (12)	0.0120 (13)	0.0116 (10)	−0.0041 (12)
C54	0.0799 (13)	0.0783 (13)	0.0691 (12)	0.0179 (11)	0.0291 (10)	0.0167 (10)
C55	0.0856 (13)	0.0558 (10)	0.0752 (12)	0.0018 (9)	0.0313 (10)	0.0071 (9)
C56	0.0692 (11)	0.0561 (10)	0.0632 (10)	−0.0044 (8)	0.0214 (8)	0.0026 (8)

Cl14—C14	1.736 (3)	C51—C56	1.389 (2)
Cl54—C54	1.741 (2)	C52—C53	1.376 (4)
O1—C1	1.218 (3)	C53—C54	1.373 (4)
O5—C5	1.214 (3)	C54—C55	1.369 (3)
C1—C2	1.513 (3)	C55—C56	1.390 (3)
C1—C11	1.495 (3)	C2—H2A	0.9700
C2—C3	1.526 (3)	C2—H2B	0.9700
C3—C4	1.548 (3)	C3—H3	0.9800
C3—C31	1.516 (2)	C4—H4A	0.9700
C4—C5	1.499 (3)	C4—H4B	0.9700
C5—C51	1.497 (3)	C12—H12	0.9300
C11—C12	1.391 (3)	C13—H13	0.9300
C11—C16	1.387 (3)	C15—H15	0.9300
C12—C13	1.378 (4)	C16—H16	0.9300
C13—C14	1.369 (4)	C32—H32	0.9300
C14—C15	1.367 (4)	C33—H33	0.9300
C15—C16	1.386 (3)	C35—H35	0.9300
C31—C32	1.386 (2)	C36—H36	0.9300
C31—C36	1.387 (3)	C37—H37A	0.9600
C32—C33	1.379 (3)	C37—H37B	0.9600
C33—C34	1.381 (3)	C37—H37C	0.9600
C34—C35	1.373 (3)	C52—H52	0.9300
C34—C37	1.512 (4)	C53—H53	0.9300
C35—C36	1.381 (3)	C55—H55	0.9300
C51—C52	1.381 (3)	C56—H56	0.9300
O1—C1—C2	121.06 (19)	C1—C2—H2B	109.00
O1—C1—C11	120.2 (2)	C3—C2—H2A	109.00
C2—C1—C11	118.76 (18)	C3—C2—H2B	109.00
C1—C2—C3	113.88 (15)	H2A—C2—H2B	108.00
C2—C3—C4	110.43 (15)	C2—C3—H3	108.00
C2—C3—C31	112.56 (14)	C4—C3—H3	108.00
C4—C3—C31	110.75 (14)	C31—C3—H3	108.00
C3—C4—C5	113.49 (16)	C3—C4—H4A	109.00
O5—C5—C4	121.0 (2)	C3—C4—H4B	109.00
O5—C5—C51	119.42 (19)	C5—C4—H4A	109.00
C4—C5—C51	119.57 (18)	C5—C4—H4B	109.00
C1—C11—C12	119.0 (2)	H4A—C4—H4B	108.00
C1—C11—C16	122.9 (2)	C11—C12—H12	119.00
C12—C11—C16	118.1 (2)	C13—C12—H12	119.00
C11—C12—C13	121.2 (2)	C12—C13—H13	120.00
C12—C13—C14	119.0 (3)	C14—C13—H13	121.00
Cl14—C14—C13	118.4 (2)	C14—C15—H15	121.00
Cl14—C14—C15	119.8 (2)	C16—C15—H15	121.00
C13—C14—C15	121.8 (2)	C11—C16—H16	119.00
C14—C15—C16	118.9 (2)	C15—C16—H16	119.00
C11—C16—C15	121.0 (2)	C31—C32—H32	120.00
C3—C31—C32	122.17 (15)	C33—C32—H32	120.00
C3—C31—C36	120.46 (15)	C32—C33—H33	119.00
C32—C31—C36	117.34 (17)	C34—C33—H33	119.00
C31—C32—C33	120.93 (18)	C34—C35—H35	119.00
C32—C33—C34	121.6 (2)	C36—C35—H35	119.00
C33—C34—C35	117.5 (2)	C31—C36—H36	119.00
C33—C34—C37	120.9 (2)	C35—C36—H36	119.00
C35—C34—C37	121.6 (2)	C34—C37—H37A	109.00
C34—C35—C36	121.5 (2)	C34—C37—H37B	109.00
C31—C36—C35	121.2 (2)	C34—C37—H37C	109.00
C5—C51—C52	118.80 (17)	H37A—C37—H37B	110.00
C5—C51—C56	122.00 (17)	H37A—C37—H37C	109.00
C52—C51—C56	119.20 (17)	H37B—C37—H37C	109.00
C51—C52—C53	120.8 (2)	C51—C52—H52	120.00
C52—C53—C54	119.2 (2)	C53—C52—H52	120.00
Cl54—C54—C53	119.08 (18)	C52—C53—H53	120.00
Cl54—C54—C55	119.21 (18)	C54—C53—H53	120.00
C53—C54—C55	121.7 (2)	C54—C55—H55	121.00
C54—C55—C56	118.8 (2)	C56—C55—H55	121.00
C51—C56—C55	120.30 (18)	C51—C56—H56	120.00
C1—C2—H2A	109.00	C55—C56—H56	120.00
O1—C1—C2—C3	3.7 (3)	C12—C13—C14—Cl14	179.28 (19)
C11—C1—C2—C3	−177.04 (16)	C12—C13—C14—C15	−1.0 (4)
O1—C1—C11—C12	−0.3 (3)	Cl14—C14—C15—C16	−179.36 (18)
O1—C1—C11—C16	178.2 (2)	C13—C14—C15—C16	0.9 (4)
C2—C1—C11—C12	−179.59 (18)	C14—C15—C16—C11	−0.1 (3)
C2—C1—C11—C16	−1.1 (3)	C3—C31—C32—C33	−178.41 (17)
C1—C2—C3—C4	72.49 (19)	C36—C31—C32—C33	−0.6 (3)
C1—C2—C3—C31	−163.18 (15)	C3—C31—C36—C35	177.69 (18)
C2—C3—C4—C5	−179.02 (16)	C32—C31—C36—C35	−0.1 (3)
C31—C3—C4—C5	55.6 (2)	C31—C32—C33—C34	1.0 (3)
C2—C3—C31—C32	−51.0 (2)	C32—C33—C34—C35	−0.6 (3)
C2—C3—C31—C36	131.25 (18)	C32—C33—C34—C37	177.7 (2)
C4—C3—C31—C32	73.1 (2)	C33—C34—C35—C36	−0.2 (3)
C4—C3—C31—C36	−104.60 (19)	C37—C34—C35—C36	−178.4 (2)
C3—C4—C5—O5	−117.3 (2)	C34—C35—C36—C31	0.5 (3)
C3—C4—C5—C51	61.6 (2)	C5—C51—C52—C53	−179.7 (2)
O5—C5—C51—C52	20.8 (3)	C56—C51—C52—C53	−0.5 (3)
O5—C5—C51—C56	−158.4 (2)	C5—C51—C56—C55	178.05 (19)
C4—C5—C51—C52	−158.1 (2)	C52—C51—C56—C55	−1.1 (3)
C4—C5—C51—C56	22.7 (3)	C51—C52—C53—C54	1.8 (4)
C1—C11—C12—C13	179.2 (2)	C52—C53—C54—Cl54	178.90 (19)
C16—C11—C12—C13	0.6 (3)	C52—C53—C54—C55	−1.4 (4)
C1—C11—C16—C15	−179.2 (2)	Cl54—C54—C55—C56	179.52 (17)
C12—C11—C16—C15	−0.7 (3)	C53—C54—C55—C56	−0.1 (4)
C11—C12—C13—C14	0.2 (4)	C54—C55—C56—C51	1.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O1	0.97	2.56	3.130 (3)	118
C16—H16···O5i	0.93	2.44	3.270 (3)	149
C55—H55···Cg2ii	0.93	2.97	3.629 (2)	129

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C31–C36 methyl­benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O1	0.97	2.56	3.130 (3)	118
C16—H16⋯O5i	0.93	2.44	3.270 (3)	149
C55—H55⋯Cg2ii	0.93	2.97	3.629 (2)	129

Symmetry codes: (i) ; (ii) .