Literature DB >> 21579502

1,4-Bis(4-chloro-phen-yl)-2-hydroxy-butane-1,4-dione.

Yongjun Liu¹, Kuiwei Yang, Weiling Song, Yan Qi.

Abstract

In the title compound, C(16)H(12)Cl(2)O(3), the benzene rings form a dihedral angle of 2.0 (3)°. Within the central O=C-CH(2)C(H)OH-C=O unit, the carbonyl groups are coplanar and lie to opposite sides [O-C⋯C-O = -170.1 (6)°]. In the crystal, inter-molecular O-H⋯O hydrogen bonds formed between the hydr-oxy groups lead to a supra-molecular chain along the c axis. In addition, the crystal packing features some very weak C-H⋯π inter-actions.

Entities: CellLine Chemical Disease Gene

Year: 2010 PMID： 21579502 PMCID： PMC2979451 DOI： 10.1107/S1600536810018027

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For the synthesis and applications of 1,4-dicarbonyl compounds, see: Ellison (1973 ▶); Hassner (1991 ▶); Ohno et al. (2001 ▶).

Experimental

Crystal data

C16H12Cl2O3 M = 323.16 Monoclinic, a = 34.800 (8) Å b = 7.4221 (14) Å c = 5.6535 (13) Å β = 95.925 (2)° V = 1452.4 (5) Å3 Z = 4 Mo Kα radiation μ = 0.45 mm−1 T = 273 K 0.12 × 0.10 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.947, T max = 0.964 3531 measured reflections 1256 independent reflections 998 reflections with I > 2σ(I) R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.057 wR(F 2) = 0.163 S = 1.05 1256 reflections 190 parameters 9 restraints H-atom parameters constrained Δρmax = 0.40 e Å−3 Δρmin = −0.21 e Å−3 Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810018027/tk2670sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018027/tk2670Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₆H₁₂Cl₂O₃	F(000) = 664
M_r = 323.16	D_x = 1.478 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1044 reflections
a = 34.800 (8) Å	θ = 2.4–24.4°
b = 7.4221 (14) Å	µ = 0.45 mm⁻¹
c = 5.6535 (13) Å	T = 273 K
β = 95.925 (2)°	Column, colourless
V = 1452.4 (5) Å³	0.12 × 0.10 × 0.08 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1256 independent reflections
Radiation source: fine-focus sealed tube	998 reflections with I > 2σ(I)
graphite	R_int = 0.025
phi and ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −38→40
T_min = 0.947, T_max = 0.964	k = −7→8
3531 measured reflections	l = −6→6

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.057	H-atom parameters constrained
wR(F²) = 0.163	w = 1/[σ²(F_o²) + (0.1063P)² + 0.4654P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
1256 reflections	Δρ_max = 0.40 e Å⁻³
190 parameters	Δρ_min = −0.21 e Å⁻³
9 restraints	Absolute structure: nd
Primary atom site location: structure-invariant direct methods

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) 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.

	x	y	z	U_iso*/U_eq
C1	1.04214 (18)	0.1713 (8)	0.3400 (11)	0.0369 (15)
H1	1.0356	0.1204	0.4809	0.044*
C2	1.0810 (2)	0.1845 (10)	0.2991 (14)	0.053 (2)
H2	1.1002	0.1385	0.4089	0.063*
C3	1.0905 (2)	0.2672 (9)	0.0921 (14)	0.049 (2)
C4	1.0605 (2)	0.3249 (10)	−0.0726 (13)	0.049 (2)
H4	1.0664	0.3745	−0.2154	0.058*
C5	1.0234 (2)	0.3116 (8)	−0.0327 (12)	0.0403 (16)
H5	1.0043	0.3556	−0.1448	0.048*
C6	1.0133 (2)	0.2332 (8)	0.1732 (12)	0.0357 (16)
C7	0.9724 (2)	0.2035 (8)	0.2253 (12)	0.0374 (16)
C8	0.9403 (2)	0.2685 (8)	0.0412 (13)	0.0383 (14)
H8	0.9443	0.2140	−0.1121	0.046*
C9	0.9007 (2)	0.2137 (9)	0.1027 (12)	0.0412 (15)
H9A	0.8999	0.0839	0.1210	0.049*
H9B	0.8961	0.2678	0.2533	0.049*
C10	0.8693 (2)	0.2712 (9)	−0.0860 (13)	0.0454 (18)
C11	0.8287 (2)	0.2621 (8)	−0.0279 (12)	0.0362 (16)
C12	0.8185 (2)	0.1854 (9)	0.1838 (11)	0.0444 (18)
H12	0.8377	0.1432	0.2964	0.053*
C13	0.7794 (2)	0.1712 (10)	0.2287 (12)	0.0465 (19)
H13	0.7725	0.1146	0.3649	0.056*
C14	0.7524 (2)	0.2427 (10)	0.0672 (14)	0.053 (2)
C15	0.7606 (2)	0.3157 (9)	−0.1456 (15)	0.0489 (18)
H15	0.7409	0.3558	−0.2564	0.059*
C16	0.7982 (2)	0.3280 (9)	−0.1908 (12)	0.0473 (18)
H16	0.8040	0.3809	−0.3319	0.057*
Cl1	1.13745 (6)	0.2822 (4)	0.0298 (3)	0.0922 (9)
Cl2	0.70386 (6)	0.2245 (4)	0.1208 (4)	0.0948 (10)
O1	0.96490 (15)	0.1328 (6)	0.4095 (9)	0.0515 (12)
O2	0.94303 (14)	0.4587 (5)	0.0178 (8)	0.0501 (10)
H2A	0.9434	0.5058	0.1492	0.075*
O3	0.87583 (16)	0.3179 (10)	−0.2824 (10)	0.084 (2)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.043 (4)	0.037 (3)	0.030 (3)	−0.007 (3)	0.002 (3)	−0.001 (3)
C2	0.066 (5)	0.056 (5)	0.035 (4)	0.005 (4)	0.000 (4)	0.001 (3)
C3	0.060 (6)	0.047 (4)	0.040 (4)	−0.008 (3)	0.000 (4)	−0.012 (3)
C4	0.057 (6)	0.053 (4)	0.037 (4)	−0.006 (3)	0.008 (4)	−0.001 (3)
C5	0.047 (4)	0.033 (3)	0.040 (4)	−0.009 (3)	0.001 (3)	0.002 (3)
C6	0.042 (4)	0.033 (3)	0.033 (4)	0.009 (3)	0.008 (3)	−0.001 (3)
C7	0.057 (4)	0.026 (3)	0.030 (4)	0.006 (3)	0.009 (3)	−0.001 (3)
C8	0.048 (3)	0.033 (3)	0.033 (3)	0.011 (2)	0.000 (3)	0.002 (3)
C9	0.047 (3)	0.047 (4)	0.031 (3)	−0.007 (3)	0.008 (3)	0.003 (3)
C10	0.043 (4)	0.057 (4)	0.037 (4)	0.006 (3)	0.008 (3)	0.003 (3)
C11	0.047 (4)	0.029 (3)	0.032 (4)	−0.010 (2)	0.003 (3)	−0.004 (3)
C12	0.053 (5)	0.055 (4)	0.026 (3)	0.013 (3)	0.004 (3)	0.006 (3)
C13	0.054 (5)	0.058 (4)	0.029 (3)	−0.017 (4)	0.013 (3)	0.005 (3)
C14	0.034 (4)	0.069 (5)	0.058 (6)	−0.011 (3)	0.014 (4)	−0.004 (4)
C15	0.027 (3)	0.055 (4)	0.062 (5)	−0.008 (3)	−0.011 (3)	0.003 (4)
C16	0.061 (5)	0.042 (3)	0.037 (4)	0.001 (3)	−0.002 (4)	0.004 (3)
Cl1	0.0472 (14)	0.147 (3)	0.0842 (18)	−0.0177 (14)	0.0152 (13)	0.0093 (17)
Cl2	0.0469 (15)	0.150 (3)	0.089 (2)	−0.0122 (14)	0.0178 (13)	0.0072 (17)
O1	0.052 (3)	0.057 (3)	0.047 (3)	0.002 (2)	0.012 (2)	0.019 (2)
O2	0.064 (3)	0.039 (2)	0.048 (2)	0.0037 (19)	0.0072 (18)	0.0049 (19)
O3	0.048 (3)	0.172 (6)	0.033 (3)	0.010 (3)	0.011 (2)	0.033 (3)

C1—C6	1.384 (10)	C9—C10	1.507 (11)
C1—C2	1.398 (10)	C9—H9A	0.9700
C1—H1	0.9300	C9—H9B	0.9700
C2—C3	1.391 (12)	C10—O3	1.206 (9)
C2—H2	0.9300	C10—C11	1.485 (10)
C3—C4	1.393 (11)	C11—C12	1.404 (9)
C3—Cl1	1.711 (8)	C11—C16	1.419 (10)
C4—C5	1.334 (9)	C12—C13	1.413 (9)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.380 (9)	C13—C14	1.349 (11)
C5—H5	0.9300	C13—H13	0.9300
C6—C7	1.499 (10)	C14—C15	1.376 (12)
C7—O1	1.218 (8)	C14—Cl2	1.753 (8)
C7—C8	1.525 (10)	C15—C16	1.361 (10)
C8—O2	1.422 (7)	C15—H15	0.9300
C8—C9	1.509 (7)	C16—H16	0.9300
C8—H8	0.9800	O2—H2A	0.8200

C6—C1—C2	120.7 (6)	C10—C9—H9A	109.3
C6—C1—H1	119.7	C8—C9—H9A	109.3
C2—C1—H1	119.7	C10—C9—H9B	109.3
C3—C2—C1	119.2 (7)	C8—C9—H9B	109.3
C3—C2—H2	120.4	H9A—C9—H9B	107.9
C1—C2—H2	120.4	O3—C10—C11	119.3 (6)
C2—C3—C4	118.1 (8)	O3—C10—C9	122.8 (6)
C2—C3—Cl1	121.1 (6)	C11—C10—C9	117.8 (6)
C4—C3—Cl1	120.6 (6)	C12—C11—C16	117.0 (7)
C5—C4—C3	122.3 (7)	C12—C11—C10	122.6 (6)
C5—C4—H4	118.8	C16—C11—C10	120.4 (6)
C3—C4—H4	118.8	C11—C12—C13	121.2 (6)
C4—C5—C6	120.7 (7)	C11—C12—H12	119.4
C4—C5—H5	119.7	C13—C12—H12	119.4
C6—C5—H5	119.7	C14—C13—C12	117.7 (6)
C5—C6—C1	118.9 (7)	C14—C13—H13	121.2
C5—C6—C7	124.0 (6)	C12—C13—H13	121.2
C1—C6—C7	117.1 (6)	C13—C14—C15	123.6 (7)
O1—C7—C6	121.4 (6)	C13—C14—Cl2	117.9 (6)
O1—C7—C8	120.9 (7)	C15—C14—Cl2	118.2 (6)
C6—C7—C8	117.6 (6)	C16—C15—C14	118.8 (7)
O2—C8—C9	111.2 (5)	C16—C15—H15	120.6
O2—C8—C7	109.0 (5)	C14—C15—H15	120.6
C9—C8—C7	112.3 (5)	C15—C16—C11	121.6 (7)
O2—C8—H8	108.1	C15—C16—H16	119.2
C9—C8—H8	108.1	C11—C16—H16	119.2
C7—C8—H8	108.1	C8—O2—H2A	109.5
C10—C9—C8	111.8 (5)

Cg1 and Cg2 are the centroids of the C1—C6 and C11—C16 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O2ⁱ	0.82	2.10	2.894 (6)	163
C1—H1···Cg1ⁱⁱ	0.93	2.89	3.507 (6)	125
C4—H4···Cg1ⁱⁱⁱ	0.93	2.97	3.600 (6)	126
C13—H13···Cg2ⁱⁱ	0.93	2.88	3.517 (6)	127
C16—H16···Cg2ⁱⁱⁱ	0.93	2.90	3.544 (6)	128

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1—C6 and C11—C16 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O2ⁱ	0.82	2.10	2.894 (6)	163
C1—H1⋯Cg1ⁱⁱ	0.93	2.89	3.507 (6)	125
C4—H4⋯Cg1ⁱⁱⁱ	0.93	2.97	3.600 (6)	126
C13—H13⋯Cg2ⁱⁱ	0.93	2.88	3.517 (6)	127
C16—H16⋯Cg2ⁱⁱⁱ	0.93	2.90	3.544 (6)	128

Symmetry codes: (i) ; (ii) ; (iii) .

2 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. Mg-promoted regio- and stereoselective C-acylation of aromatic alpha,beta-unsaturated carbonyl compounds.

Authors: T Ohno; M Sakai; Y Ishino; T Shibata; H Maekawa; I Nishiguchi
Journal: Org Lett Date: 2001-11-01 Impact factor: 6.005

2 in total