Literature DB >> 25309219

Crystal structure of (Z)-2,3-di-chloro-1,4-bis-(4-meth-oxy-phen-yl)but-2-ene-1,4-dione.

Ram K Tittal1, Satish Kumar2, R N Ram1.   

Abstract

The title compound, C18H14Cl2O4, adopts a Z conformation around the cental C=C bond. The two aromatic rings of the mol-ecule are nearly perpendicular to each other, with a dihedral angle between of 86.22 (14)°. The meth-oxy substituents lie close to the plane of the attached benzene rings. The C(ar)-C(ar)-O-C(Me) torsion angles are -2.4 (7) and 7.5 (6)°. Weak C-H⋯O inter-actions link the mol-ecules forming a three-dimensional network. The crystal packing also displays short [3.160 (3) Å] Cl⋯O halogen-bonding contacts between mol-ecules related by the screw axis. The structure exhibits disorder of one carbonyl O atom with a refined occupancy ratio of 0.21 (6):0.79 (6).

Entities:  

Keywords:  2,3-di­chloro­but-2-ene-1,4-dione; CuCl/bpy; crystal structure; di­chloro­methyl radical; stereoselectivity; tri­chloro­methyl groups

Year:  2014        PMID： 25309219      PMCID： PMC4186131          DOI： 10.1107/S1600536814018790

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


Related literature

For a review of radical reactions, see: Clark (2002 ▶); Ram & Tittal (2014a ▶,b ▶); Pintauer & Matyjaszewski (2008 ▶). For details of the synthesis, see: Kurosawa & Yamaguchi (1981 ▶); Ram et al. (2007 ▶). For halogen-bond inter­actions, see: Agarwal et al. (2014 ▶). For a similar structure and short aromatic contacts, see: Tittal et al. (2014 ▶).

Experimental

Crystal data

C18H14Cl2O4 M = 365.19 Monoclinic, a = 8.877 (3) Å b = 9.914 (3) Å c = 10.294 (3) Å β = 110.565 (5)° V = 848.3 (5) Å3 Z = 2 Mo Kα radiation μ = 0.40 mm−1 T = 273 K 0.31 × 0.23 × 0.14 mm

Data collection

Bruker SMART APEX CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.860, T max = 1.000 9879 measured reflections 4012 independent reflections 3755 reflections with I > 2σ(I) R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.057 wR(F 2) = 0.134 S = 1.17 4012 reflections 223 parameters 2 restraints H-atom parameters constrained Δρmax = 0.41 e Å−3 Δρmin = −0.17 e Å−3 Absolute structure: Flack x determined using 1548 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▶) Absolute structure parameter: 0.01 (2)

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: OLEX2, PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶). Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814018790/fy2117sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814018790/fy2117Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814018790/fy2117Isup3.cml Click here for additional data file. . DOI: 10.1107/S1600536814018790/fy2117fig1.tif Mol­ecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms. Click here for additional data file. . DOI: 10.1107/S1600536814018790/fy2117fig2.tif A view of the crystal packing of the title compound. A weak C—H⋯O hydrogen bond is shown as a dashed line. Click here for additional data file. . DOI: 10.1107/S1600536814018790/fy2117fig3.tif Part of the structure of the title compound showing O⋯·Cl and C—H⋯·O inter­actions. CCDC reference: 1019996 Additional supporting information: crystallographic information; 3D view; checkCIF report
C18H14Cl2O4F(000) = 376
Mr = 365.19Dx = 1.430 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 8.877 (3) ÅCell parameters from 5754 reflections
b = 9.914 (3) Åθ = 3.2–26.1°
c = 10.294 (3) ŵ = 0.40 mm−1
β = 110.565 (5)°T = 273 K
V = 848.3 (5) Å3Block, colorless
Z = 20.31 × 0.23 × 0.14 mm
Bruker SMART APEX CCD diffractometer3755 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
φ and ω scansθmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −11→11
Tmin = 0.860, Tmax = 1.000k = −12→13
9879 measured reflectionsl = −13→13
4012 independent reflections
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.057w = 1/[σ2(Fo2) + (0.0741P)2 + 0.0555P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.134(Δ/σ)max < 0.001
S = 1.17Δρmax = 0.41 e Å−3
4012 reflectionsΔρmin = −0.17 e Å−3
223 parametersAbsolute structure: Flack x determined using 1548 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
2 restraintsAbsolute structure parameter: 0.01 (2)
Primary atom site location: structure-invariant direct methods
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
xyzUiso*/UeqOcc. (<1)
C10.6776 (4)0.5542 (4)0.2160 (4)0.0447 (8)
C20.5707 (5)0.6341 (4)0.1270 (4)0.0443 (8)
C30.6859 (4)0.3333 (4)0.3536 (4)0.0424 (7)
C40.1894 (4)1.0044 (4)0.1824 (4)0.0456 (8)
C60.3256 (4)0.7652 (4)0.1360 (4)0.0420 (7)
C70.7162 (5)0.1437 (5)0.5065 (4)0.0505 (9)
H70.70530.10590.58540.061*
C80.7473 (4)0.2551 (4)0.2713 (3)0.0444 (8)
H80.75670.29250.19160.053*
C90.7798 (4)0.0673 (4)0.4242 (4)0.0449 (8)
C110.0916 (5)0.9011 (5)0.1102 (5)0.0544 (10)
H11−0.01960.91190.07690.065*
C120.1581 (4)0.7821 (4)0.0872 (4)0.0507 (9)
H120.09160.71250.03910.061*
C130.6700 (5)0.2740 (4)0.4710 (4)0.0494 (9)
H130.62710.32420.52610.059*
C140.7946 (5)0.1233 (4)0.3056 (4)0.0463 (8)
H140.83600.07250.24990.056*
C150.6357 (5)0.4749 (4)0.3229 (4)0.0535 (9)
O4A0.516 (5)0.509 (5)0.347 (7)0.088 (5)0.20 (6)
O4B0.569 (3)0.5385 (17)0.390 (2)0.088 (5)0.80 (6)
C160.3938 (5)0.6362 (4)0.1112 (5)0.0496 (9)
C180.4208 (4)0.8699 (4)0.2085 (4)0.0463 (8)
H180.53200.85980.24170.056*
C200.9065 (6)−0.1371 (5)0.3997 (6)0.0724 (14)
H20A0.8372−0.15260.30550.109*
H20B0.9380−0.22210.44600.109*
H20C1.0004−0.08880.40030.109*
C210.3548 (4)0.9895 (4)0.2329 (4)0.0456 (8)
H210.42081.05870.28260.055*
C220.2043 (6)1.2268 (6)0.2784 (6)0.0742 (14)
H22A0.27951.25710.23670.111*
H22B0.26171.19720.37150.111*
H22C0.13371.29960.28000.111*
O10.1126 (4)1.1181 (3)0.2000 (4)0.0633 (8)
O20.8234 (4)−0.0603 (3)0.4692 (3)0.0620 (8)
O30.3164 (4)0.5356 (4)0.0744 (6)0.0929 (14)
Cl10.62060 (13)0.74187 (12)0.01732 (11)0.0625 (3)
Cl20.87618 (12)0.54992 (12)0.22528 (13)0.0651 (3)
U11U22U33U12U13U23
C10.0420 (17)0.0381 (17)0.0560 (19)0.0057 (16)0.0198 (15)−0.0067 (16)
C20.0487 (19)0.0387 (18)0.0471 (19)−0.0001 (15)0.0186 (16)−0.0032 (14)
C30.0382 (16)0.0429 (19)0.0446 (17)0.0046 (15)0.0126 (14)−0.0020 (14)
C40.0460 (18)0.0446 (19)0.048 (2)0.0078 (15)0.0193 (16)0.0042 (15)
C60.0404 (17)0.0397 (19)0.0452 (17)0.0031 (15)0.0141 (13)0.0032 (14)
C70.052 (2)0.053 (2)0.049 (2)−0.0062 (18)0.0214 (17)0.0025 (17)
C80.0446 (18)0.048 (2)0.0401 (16)0.0033 (17)0.0146 (14)−0.0021 (15)
C90.0390 (16)0.0403 (19)0.0507 (19)−0.0057 (15)0.0098 (15)−0.0021 (15)
C110.0343 (18)0.061 (3)0.064 (2)0.0039 (17)0.0122 (17)−0.0033 (19)
C120.0400 (18)0.050 (2)0.058 (2)−0.0061 (16)0.0123 (16)−0.0080 (17)
C130.050 (2)0.052 (2)0.052 (2)0.0006 (17)0.0252 (16)−0.0062 (17)
C140.0454 (19)0.0433 (19)0.0496 (19)0.0016 (16)0.0161 (16)−0.0090 (16)
C150.060 (2)0.049 (2)0.056 (2)0.0144 (19)0.0261 (19)0.0014 (18)
O4A0.131 (10)0.066 (5)0.099 (8)0.046 (6)0.079 (8)0.018 (5)
O4B0.131 (10)0.066 (5)0.099 (8)0.046 (6)0.079 (8)0.018 (5)
C160.0439 (19)0.0402 (19)0.061 (2)0.0017 (16)0.0140 (17)−0.0052 (17)
C180.0321 (16)0.047 (2)0.055 (2)0.0029 (15)0.0091 (15)0.0002 (16)
C200.073 (3)0.046 (2)0.086 (3)0.019 (2)0.013 (2)−0.001 (2)
C210.0411 (18)0.0391 (18)0.053 (2)−0.0010 (15)0.0124 (16)−0.0070 (15)
C220.074 (3)0.060 (3)0.089 (3)0.014 (3)0.029 (3)−0.018 (3)
O10.0521 (16)0.0538 (19)0.083 (2)0.0161 (14)0.0219 (15)−0.0103 (16)
O20.072 (2)0.0416 (16)0.0703 (19)0.0056 (14)0.0220 (15)0.0056 (13)
O30.0590 (18)0.050 (2)0.166 (4)−0.0067 (17)0.035 (2)−0.032 (2)
Cl10.0694 (6)0.0620 (6)0.0619 (6)0.0065 (6)0.0302 (5)0.0126 (5)
Cl20.0461 (5)0.0549 (6)0.0968 (8)0.0105 (5)0.0284 (5)0.0012 (6)
C1—C21.326 (5)C9—O21.356 (5)
C1—C151.502 (6)C11—H110.9300
C1—Cl21.732 (3)C11—C121.377 (6)
C2—C161.521 (5)C12—H120.9300
C2—Cl11.722 (4)C13—H130.9300
C3—C81.393 (5)C14—H140.9300
C3—C131.395 (6)C15—O4A1.219 (13)
C3—C151.473 (6)C15—O4B1.229 (8)
C4—C111.379 (6)C16—O31.195 (5)
C4—C211.383 (5)C18—H180.9300
C4—O11.362 (5)C18—C211.384 (6)
C6—C121.402 (5)C20—H20A0.9600
C6—C161.476 (5)C20—H20B0.9600
C6—C181.380 (5)C20—H20C0.9600
C7—H70.9300C20—O21.417 (6)
C7—C91.395 (6)C21—H210.9300
C7—C131.367 (6)C22—H22A0.9600
C8—H80.9300C22—H22B0.9600
C8—C141.380 (6)C22—H22C0.9600
C9—C141.389 (6)C22—O11.419 (6)
C2—C1—C15121.2 (3)C7—C13—H13119.4
C2—C1—Cl2121.4 (3)C8—C14—C9119.3 (3)
C15—C1—Cl2117.1 (3)C8—C14—H14120.4
C1—C2—C16122.9 (4)C9—C14—H14120.4
C1—C2—Cl1122.5 (3)C3—C15—C1121.4 (3)
C16—C2—Cl1114.6 (3)O4A—C15—C1117 (2)
C8—C3—C13118.3 (3)O4A—C15—C3116 (2)
C8—C3—C15123.6 (4)O4B—C15—C1115.8 (6)
C13—C3—C15118.2 (3)O4B—C15—C3122.5 (6)
C11—C4—C21120.5 (4)C6—C16—C2117.7 (3)
O1—C4—C11115.9 (3)O3—C16—C2118.7 (4)
O1—C4—C21123.6 (4)O3—C16—C6123.6 (4)
C12—C6—C16119.3 (3)C6—C18—H18119.2
C18—C6—C12118.4 (3)C6—C18—C21121.6 (3)
C18—C6—C16122.3 (3)C21—C18—H18119.2
C9—C7—H7120.0H20A—C20—H20B109.5
C13—C7—H7120.0H20A—C20—H20C109.5
C13—C7—C9119.9 (4)H20B—C20—H20C109.5
C3—C8—H8119.3O2—C20—H20A109.5
C14—C8—C3121.3 (4)O2—C20—H20B109.5
C14—C8—H8119.3O2—C20—H20C109.5
C14—C9—C7120.0 (4)C4—C21—C18119.0 (3)
O2—C9—C7115.3 (3)C4—C21—H21120.5
O2—C9—C14124.7 (4)C18—C21—H21120.5
C4—C11—H11119.9H22A—C22—H22B109.5
C12—C11—C4120.1 (3)H22A—C22—H22C109.5
C12—C11—H11119.9H22B—C22—H22C109.5
C6—C12—H12119.8O1—C22—H22A109.5
C11—C12—C6120.4 (4)O1—C22—H22B109.5
C11—C12—H12119.8O1—C22—H22C109.5
C3—C13—H13119.4C4—O1—C22119.3 (3)
C7—C13—C3121.2 (4)C9—O2—C20117.7 (4)
C1—C2—C16—C6121.1 (4)C13—C7—C9—C14−0.6 (6)
C1—C2—C16—O3−61.8 (6)C13—C7—C9—O2179.4 (4)
C2—C1—C15—C3137.3 (4)C14—C9—O2—C207.5 (6)
C2—C1—C15—O4A−17 (4)C15—C1—C2—C16−9.4 (6)
C2—C1—C15—O4B−48.1 (18)C15—C1—C2—Cl1171.9 (3)
C3—C8—C14—C90.3 (6)C15—C3—C8—C14179.1 (4)
C4—C11—C12—C6−0.5 (7)C15—C3—C13—C7−179.1 (4)
C6—C18—C21—C4−0.5 (6)C16—C6—C12—C11179.4 (4)
C7—C9—C14—C80.6 (6)C16—C6—C18—C21−178.9 (4)
C7—C9—O2—C20−172.5 (4)C18—C6—C12—C110.7 (6)
C8—C3—C13—C71.3 (6)C18—C6—C16—C2−18.6 (6)
C8—C3—C15—C1−12.4 (6)C18—C6—C16—O3164.4 (5)
C8—C3—C15—O4A142 (4)C21—C4—C11—C12−0.3 (7)
C8—C3—C15—O4B173.5 (19)C21—C4—O1—C22−2.4 (7)
C9—C7—C13—C3−0.4 (6)O1—C4—C11—C12−180.0 (4)
C11—C4—C21—C180.8 (6)O1—C4—C21—C18−179.6 (4)
C11—C4—O1—C22177.3 (4)O2—C9—C14—C8−179.4 (3)
C12—C6—C16—C2162.7 (4)Cl1—C2—C16—C6−60.1 (4)
C12—C6—C16—O3−14.2 (7)Cl1—C2—C16—O3117.0 (5)
C12—C6—C18—C21−0.2 (6)Cl2—C1—C2—C16177.2 (3)
C13—C3—C8—C14−1.3 (5)Cl2—C1—C2—Cl1−1.5 (5)
C13—C3—C15—C1168.0 (4)Cl2—C1—C15—C3−49.0 (5)
C13—C3—C15—O4A−38 (4)Cl2—C1—C15—O4A157 (4)
C13—C3—C15—O4B−6.1 (19)Cl2—C1—C15—O4B125.5 (17)
D—H···AD—HH···AD···AD—H···A
C7—H7···O4Ai0.932.493.23 (3)137
C7—H7···O4Bi0.932.623.245 (9)125
C12—H12···O1ii0.932.663.488 (5)149
C14—H14···O1iii0.932.723.363 (5)127
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C7—H7⋯O4A i 0.932.493.23 (3)137
C7—H7⋯O4B i 0.932.623.245 (9)125
C12—H12⋯O1ii 0.932.663.488 (5)149
C14—H14⋯O1iii 0.932.723.363 (5)127

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

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7.  (Z)-2,3-Di-chloro-1,4-bis-(4-chloro-phen-yl)but-2-ene-1,4-dione.

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