organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2414-3146

(1E,4E)-1,5-Bis(2,6-di­chloro­phen­yl)penta-1,4-dien-3-one

aPG and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India, bDepartment of Physics, Bharathi Women's College, Chennai-108, Tamilnadu, India, and cPG Department of Physics, Bhaktavatsalam Memorial College for Women, Chennai-80, Tamilnadu, India
*Correspondence e-mail: guqmc@yahoo.com

Edited by P. C. Healy, Griffith University, Australia (Received 28 November 2017; accepted 20 December 2017; online 9 January 2018)

The asymmetric unit of the title compound, C17H10Cl4O, consists of one independent mol­ecule and two mol­ecules each located on twofold symmetry axes through the central C=O bond such that they each contribute half a mol­ecule each to the asymmetric unit. The dihedral angles between the rings in the three molecules are 73.1 (3), 65.3 (3) and 75.4 (3)°. In the crystal, mol­ecules are linked through C—H⋯O hydrogen bonds, generating undulated mol­ecular sheets lying parallel to (110).

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

In the asymmetric unit of the title compound (Fig. 1[link]), one independent mol­ecule and two mol­ecules each located on twofold symmetry axes through the central C=O bond such that they each contribute half a mol­ecule each to the asymmetric unit. The atoms C33 and C34 of the B mol­ecule (C27–C35/Cl1/Cl2/O) are disordered over two sets of sites with occupancy factors of 0.471 (14) and 0.529 (14). No abnormalities are observed in the bond lengths and angles of the asymmetric unit mol­ecules and are typical of such compounds (Huang et al., 2011[Huang, J.-D., Tang, Q.-Q., Chen, X.-Y., Ye, Y. & Wang, Y. (2011). Acta Cryst. E67, o758.]).

[Figure 1]
Figure 1
An ORTEP plot of the title compound with three mol­ecules in the asymmetric unit, with displacement ellipsoids drawn at 20% probability level. Both disorder components are shown. [Symmetry codes: (a) −x, 1 − y, z; (b) −x + [{1\over 2}], −y + [{3\over 2}], z.]

In the crystal, the mol­ecules are linked primarily via C—H⋯O hydrogen bonds, forming mol­ecular chains (Table 1[link] and Fig. 2[link]) with C—H⋯Cl hydrogen bonds also contributing to the cohesion of the crystal.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C14—H14⋯Cl4i 0.93 2.86 3.750 (6) 162
C25—H25⋯O3ii 0.93 2.57 3.444 (8) 156
C30—H30⋯Cl7i 0.93 2.90 3.784 (8) 159
Symmetry codes: (i) [-x+{\script{1\over 4}}, y-{\script{1\over 4}}, z-{\script{1\over 4}}]; (ii) [x-{\script{1\over 4}}, -y+{\script{5\over 4}}, z-{\script{1\over 4}}].
[Figure 2]
Figure 2
Crystal packing of the title compound. The dashed lines indicate hydrogen bonding. Hydrogen atoms not involved in hydrogen bonding are omitted for clarity.

Synthesis and crystallization

The title compound was synthesized by following the published procedure (Lee et al., 2009[Lee, K., Ab Aziz, F. H., Syahida, A., Abas, F., Shaari, K., Israf, D. A. & Lajis, N. H. (2009). Eur. J. Med. Chem. 44, 3195-3200.]). A mixture of 2,6 dicholorobenzaldehyde (4.8 g, 0.027 mol) and acetone (1 ml) in the presence of 10% NaOH along with 50 ml methanol was prepared and the solution was stirred for about 15 h. Ice cubes were added to enhance the precipitation. The resultant precipitate was collected and washed with distilled water to drain excess NaOH from the product. Single crystals of diffraction quality were grown from chloro­form solution by slow evaporation (m.p. 371 K).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. Atoms C33 and C34 are disordered over two sets of sites [occupancy ratio 0.471 (14):0.529 (14)].

Table 2
Experimental details

Crystal data
Chemical formula C17H10Cl4O
Mr 372.05
Crystal system, space group Orthorhombic, Fdd2
Temperature (K) 296
a, b, c (Å) 28.1477 (8), 17.3385 (7), 26.1837 (10)
V3) 12778.7 (8)
Z 32
Radiation type Mo Kα
μ (mm−1) 0.74
Crystal size (mm) 0.20 × 0.20 × 0.15
 
Data collection
Diffractometer Bruker Kappa APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.863, 0.895
No. of measured, independent and observed [I > 2σ(I)] reflections 37791, 5641, 4336
Rint 0.056
(sin θ/λ)max−1) 0.595
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.085, 1.03
No. of reflections 5633
No. of parameters 418
No. of restraints 64
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.46, −0.47
Absolute structure Flack x determined using 1755 quotients [(I+)−(I)]/[(I+)+(I)] (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.])
Absolute structure parameter −0.01 (2)
Computer programs: APEX2, SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXT2014 (Sheldrick, 2015a[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), SHELXL2014 (Sheldrick, 2015b[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]) and ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Structural data


Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b).

(1E,4E)-1,5-Bis(2,6-dichlorophenyl)penta-1,4-dien-3-one top
Crystal data top
C17H10Cl4ODx = 1.547 Mg m3
Mr = 372.05Melting point: 371 K
Orthorhombic, Fdd2Mo Kα radiation, λ = 0.71073 Å
a = 28.1477 (8) ÅCell parameters from 6475 reflections
b = 17.3385 (7) Åθ = 2.7–21.9°
c = 26.1837 (10) ŵ = 0.74 mm1
V = 12778.7 (8) Å3T = 296 K
Z = 32Block, yellow
F(000) = 60160.20 × 0.20 × 0.15 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
5641 independent reflections
Radiation source: fine-focus sealed tube4336 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
ω and φ scanθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 3233
Tmin = 0.863, Tmax = 0.895k = 2020
37791 measured reflectionsl = 3131
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.040 w = 1/[σ2(Fo2) + (0.0294P)2 + 21.0031P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.085(Δ/σ)max < 0.001
S = 1.03Δρmax = 0.46 e Å3
5633 reflectionsΔρmin = 0.47 e Å3
418 parametersAbsolute structure: Flack x determined using 1755 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
64 restraintsAbsolute structure parameter: 0.01 (2)
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.

Refinement. H atoms were positioned geometrically and treated as riding on their parent atoms and refined with, C—H distance of 0.93 Å.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.11267 (18)1.0169 (3)0.15237 (19)0.0423 (13)
C20.15359 (19)1.0469 (3)0.1311 (2)0.0496 (14)
H20.15181.07930.10290.060*
C30.1968 (2)1.0285 (3)0.1519 (2)0.0572 (16)
H30.22451.04890.13800.069*
C40.19913 (18)0.9798 (3)0.1935 (2)0.0525 (15)
H40.22840.96610.20710.063*
C50.15811 (18)0.9516 (3)0.2146 (2)0.0446 (13)
C60.11302 (17)0.9690 (3)0.19511 (19)0.0389 (12)
C70.06800 (17)0.9365 (3)0.2143 (2)0.0404 (12)
H70.04690.91850.18960.049*
C80.05401 (16)0.9301 (3)0.2622 (2)0.0407 (12)
H80.07450.94840.28730.049*
C90.00870 (15)0.8964 (3)0.2793 (2)0.0394 (12)
C100.02339 (18)0.8609 (3)0.2416 (2)0.0453 (13)
H100.01330.85480.20800.054*
C110.06613 (17)0.8379 (3)0.2548 (2)0.0403 (12)
H110.07340.84330.28930.048*
C120.10397 (16)0.8048 (3)0.22319 (19)0.0398 (12)
C130.09792 (18)0.7573 (3)0.1799 (2)0.0478 (14)
C140.1352 (2)0.7286 (4)0.1525 (2)0.0584 (16)
H140.12970.69730.12430.070*
C150.18132 (19)0.7462 (4)0.1668 (2)0.0590 (17)
H150.20680.72710.14800.071*
C160.18946 (18)0.7915 (3)0.2083 (2)0.0510 (14)
H160.22040.80330.21790.061*
C170.15191 (17)0.8196 (3)0.23576 (19)0.0403 (12)
C180.16222 (18)0.4241 (3)0.3399 (2)0.0491 (14)
C190.2023 (2)0.4001 (3)0.3140 (3)0.0608 (17)
H190.23220.41660.32440.073*
C200.1977 (2)0.3517 (4)0.2729 (3)0.0699 (19)
H200.22460.33570.25510.084*
C210.1535 (2)0.3268 (4)0.2580 (2)0.0608 (17)
H210.15030.29340.23040.073*
C220.11380 (17)0.3517 (3)0.2843 (2)0.0513 (15)
C230.11649 (17)0.4019 (3)0.3262 (2)0.0431 (13)
C240.07580 (18)0.4322 (3)0.3552 (2)0.0490 (14)
H240.07720.42890.39070.059*
C250.03839 (19)0.4629 (3)0.3354 (2)0.0507 (14)
H250.03510.46200.30000.061*
C260.00000.50000.3665 (4)0.057 (2)
C270.09628 (19)0.6931 (3)0.3546 (2)0.0588 (16)
C280.05807 (18)0.6714 (3)0.3254 (2)0.0537 (15)
H280.02750.68580.33500.064*
C290.0650 (2)0.6288 (4)0.2826 (3)0.0643 (17)
H290.03910.61390.26290.077*
C300.1100 (2)0.6077 (4)0.2681 (3)0.0722 (19)
H300.11460.57790.23900.087*
C310.1477 (2)0.6308 (4)0.2967 (3)0.074 (2)
C320.14291 (19)0.6749 (4)0.3408 (3)0.071 (2)
C330.1775 (4)0.6990 (8)0.3877 (6)0.045 (4)0.471 (14)
H330.16910.68700.42110.054*0.471 (14)
C340.2169 (4)0.7348 (8)0.3785 (6)0.052 (4)0.471 (14)
H340.22350.75100.34540.063*0.471 (14)
C33'0.1895 (4)0.7043 (6)0.3532 (5)0.050 (3)0.529 (14)
H33'0.21070.71750.32740.060*0.529 (14)
C34'0.2015 (5)0.7121 (9)0.4010 (5)0.054 (4)0.529 (14)
H34'0.18080.69470.42610.064*0.529 (14)
C350.25000.75000.4180 (3)0.056 (2)
O10.00129 (11)0.8985 (2)0.32475 (14)0.0559 (10)
O20.00000.50000.4127 (3)0.081 (2)
O30.25000.75000.4629 (2)0.0734 (18)
Cl10.05851 (5)1.04252 (9)0.12522 (6)0.0594 (4)
Cl20.16449 (5)0.88981 (11)0.26605 (7)0.0744 (5)
Cl30.04160 (5)0.72921 (11)0.16049 (7)0.0731 (5)
Cl40.16511 (5)0.87707 (9)0.28818 (6)0.0567 (4)
Cl50.16975 (6)0.48515 (9)0.39223 (6)0.0666 (5)
Cl60.05927 (5)0.31438 (10)0.26448 (6)0.0669 (4)
Cl70.08458 (7)0.74969 (13)0.40754 (9)0.1053 (8)
Cl80.20421 (6)0.60238 (12)0.27670 (11)0.1188 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.045 (3)0.048 (3)0.034 (3)0.001 (3)0.002 (2)0.001 (3)
C20.052 (3)0.052 (3)0.045 (4)0.007 (3)0.007 (3)0.010 (3)
C30.046 (3)0.061 (4)0.065 (4)0.007 (3)0.019 (3)0.007 (3)
C40.035 (3)0.059 (4)0.064 (4)0.005 (3)0.005 (3)0.006 (3)
C50.039 (3)0.045 (3)0.050 (3)0.003 (2)0.007 (2)0.009 (3)
C60.038 (3)0.038 (3)0.040 (3)0.005 (2)0.003 (2)0.002 (2)
C70.036 (3)0.042 (3)0.043 (3)0.008 (2)0.003 (2)0.003 (3)
C80.036 (3)0.051 (3)0.035 (3)0.007 (2)0.004 (2)0.002 (3)
C90.032 (3)0.047 (3)0.039 (3)0.004 (2)0.002 (2)0.004 (3)
C100.041 (3)0.061 (4)0.034 (3)0.012 (3)0.001 (2)0.008 (3)
C110.037 (3)0.043 (3)0.040 (3)0.002 (2)0.000 (2)0.005 (2)
C120.035 (3)0.045 (3)0.039 (3)0.007 (2)0.004 (2)0.005 (3)
C130.037 (3)0.058 (4)0.048 (4)0.005 (3)0.005 (2)0.001 (3)
C140.056 (4)0.075 (4)0.044 (4)0.007 (3)0.002 (3)0.013 (3)
C150.038 (3)0.078 (4)0.061 (4)0.015 (3)0.007 (3)0.010 (4)
C160.034 (3)0.062 (4)0.057 (4)0.004 (3)0.000 (3)0.003 (3)
C170.033 (3)0.042 (3)0.046 (3)0.005 (2)0.002 (2)0.001 (3)
C180.043 (3)0.047 (3)0.058 (4)0.000 (3)0.003 (3)0.007 (3)
C190.036 (3)0.055 (4)0.091 (5)0.000 (3)0.001 (3)0.003 (4)
C200.048 (4)0.066 (4)0.096 (6)0.003 (3)0.011 (4)0.000 (4)
C210.060 (4)0.057 (4)0.066 (4)0.007 (3)0.010 (3)0.003 (3)
C220.038 (3)0.054 (3)0.062 (4)0.003 (3)0.001 (3)0.010 (3)
C230.039 (3)0.042 (3)0.049 (3)0.000 (2)0.002 (2)0.008 (3)
C240.043 (3)0.055 (4)0.048 (4)0.001 (3)0.002 (3)0.006 (3)
C250.045 (3)0.059 (4)0.049 (4)0.001 (3)0.005 (3)0.004 (3)
C260.034 (4)0.063 (6)0.074 (7)0.001 (4)0.0000.000
C270.041 (3)0.052 (4)0.083 (5)0.005 (3)0.016 (3)0.002 (3)
C280.034 (3)0.056 (4)0.070 (4)0.005 (3)0.004 (3)0.003 (3)
C290.051 (4)0.074 (5)0.067 (5)0.005 (3)0.006 (3)0.007 (4)
C300.076 (5)0.064 (4)0.077 (5)0.002 (4)0.019 (4)0.013 (4)
C310.042 (4)0.057 (4)0.123 (7)0.001 (3)0.024 (4)0.028 (4)
C320.037 (3)0.047 (4)0.129 (6)0.007 (3)0.016 (4)0.014 (4)
C330.042 (7)0.060 (7)0.034 (8)0.008 (6)0.003 (6)0.015 (7)
C340.042 (7)0.080 (9)0.034 (8)0.022 (6)0.012 (6)0.014 (7)
C33'0.043 (7)0.049 (6)0.058 (8)0.003 (5)0.004 (6)0.013 (6)
C34'0.050 (9)0.071 (8)0.040 (8)0.008 (7)0.007 (7)0.013 (6)
C350.042 (5)0.083 (6)0.042 (5)0.012 (4)0.0000.000
O10.044 (2)0.087 (3)0.038 (2)0.0066 (19)0.0018 (17)0.001 (2)
O20.060 (4)0.118 (6)0.066 (5)0.016 (4)0.0000.000
O30.074 (4)0.106 (5)0.040 (4)0.001 (3)0.0000.000
Cl10.0509 (8)0.0797 (11)0.0476 (9)0.0002 (7)0.0032 (7)0.0106 (8)
Cl20.0428 (8)0.0948 (13)0.0857 (12)0.0048 (8)0.0023 (8)0.0453 (11)
Cl30.0445 (9)0.0937 (12)0.0811 (12)0.0003 (8)0.0166 (8)0.0252 (10)
Cl40.0433 (8)0.0685 (10)0.0581 (9)0.0003 (7)0.0047 (7)0.0120 (8)
Cl50.0561 (9)0.0670 (10)0.0768 (12)0.0040 (7)0.0114 (8)0.0088 (9)
Cl60.0511 (8)0.0788 (11)0.0707 (11)0.0064 (8)0.0010 (8)0.0184 (9)
Cl70.0755 (14)0.1122 (16)0.1282 (18)0.0179 (11)0.0433 (12)0.0494 (14)
Cl80.0568 (10)0.0889 (15)0.211 (3)0.0153 (10)0.0501 (14)0.0386 (17)
Geometric parameters (Å, º) top
C1—C21.381 (7)C20—C211.374 (8)
C1—C61.394 (7)C20—H200.9300
C1—Cl11.740 (5)C21—C221.383 (7)
C2—C31.370 (8)C21—H210.9300
C2—H20.9300C22—C231.402 (8)
C3—C41.380 (8)C22—Cl61.745 (5)
C3—H30.9300C23—C241.472 (7)
C4—C51.370 (7)C24—C251.290 (7)
C4—H40.9300C24—H240.9300
C5—C61.401 (7)C25—C261.498 (8)
C5—Cl21.731 (5)C25—H250.9300
C6—C71.474 (7)C26—O21.211 (10)
C7—C81.320 (7)C26—C25i1.498 (8)
C7—H70.9300C27—C281.371 (7)
C8—C91.473 (7)C27—C321.397 (8)
C8—H80.9300C27—Cl71.731 (7)
C9—O11.224 (6)C28—C291.357 (8)
C9—C101.473 (7)C28—H280.9300
C10—C111.314 (7)C29—C301.371 (8)
C10—H100.9300C29—H290.9300
C11—C121.466 (7)C30—C311.360 (9)
C11—H110.9300C30—H300.9300
C12—C131.411 (7)C31—C321.393 (10)
C12—C171.413 (7)C31—Cl81.744 (6)
C13—C141.367 (7)C32—C33'1.444 (11)
C13—Cl31.735 (5)C32—C331.622 (15)
C14—C151.385 (8)C33—C341.293 (16)
C14—H140.9300C33—H330.9300
C15—C161.360 (8)C34—C351.418 (12)
C15—H150.9300C34—C34ii1.94 (2)
C16—C171.368 (7)C34—H340.9300
C16—H160.9300C33'—C34'1.303 (16)
C17—Cl41.736 (5)C33'—H33'0.9300
C18—C191.380 (8)C34'—C351.578 (13)
C18—C231.391 (7)C34'—H34'0.9300
C18—Cl51.744 (6)C35—O31.177 (9)
C19—C201.371 (9)C35—C34ii1.418 (12)
C19—H190.9300C35—C34'ii1.578 (13)
C2—C1—C6122.8 (5)C20—C21—C22119.5 (6)
C2—C1—Cl1118.0 (4)C20—C21—H21120.3
C6—C1—Cl1119.1 (4)C22—C21—H21120.3
C3—C2—C1119.6 (5)C21—C22—C23122.8 (5)
C3—C2—H2120.2C21—C22—Cl6116.5 (5)
C1—C2—H2120.2C23—C22—Cl6120.7 (4)
C2—C3—C4119.8 (5)C18—C23—C22115.1 (5)
C2—C3—H3120.1C18—C23—C24119.2 (5)
C4—C3—H3120.1C22—C23—C24125.7 (5)
C5—C4—C3119.8 (5)C25—C24—C23125.1 (5)
C5—C4—H4120.1C25—C24—H24117.5
C3—C4—H4120.1C23—C24—H24117.5
C4—C5—C6122.7 (5)C24—C25—C26123.1 (6)
C4—C5—Cl2116.6 (4)C24—C25—H25118.4
C6—C5—Cl2120.7 (4)C26—C25—H25118.4
C1—C6—C5115.3 (4)O2—C26—C25122.9 (4)
C1—C6—C7119.6 (5)O2—C26—C25i122.9 (4)
C5—C6—C7125.0 (5)C25—C26—C25i114.1 (8)
C8—C7—C6127.8 (5)C28—C27—C32122.1 (6)
C8—C7—H7116.1C28—C27—Cl7116.9 (5)
C6—C7—H7116.1C32—C27—Cl7120.9 (5)
C7—C8—C9125.5 (5)C29—C28—C27119.7 (5)
C7—C8—H8117.2C29—C28—H28120.1
C9—C8—H8117.2C27—C28—H28120.1
O1—C9—C8118.9 (4)C28—C29—C30120.5 (6)
O1—C9—C10121.6 (4)C28—C29—H29119.8
C8—C9—C10119.5 (5)C30—C29—H29119.8
C11—C10—C9120.7 (5)C31—C30—C29119.3 (7)
C11—C10—H10119.6C31—C30—H30120.3
C9—C10—H10119.6C29—C30—H30120.3
C10—C11—C12129.4 (5)C30—C31—C32122.8 (6)
C10—C11—H11115.3C30—C31—Cl8117.6 (7)
C12—C11—H11115.3C32—C31—Cl8119.5 (6)
C13—C12—C17114.1 (4)C31—C32—C27115.4 (6)
C13—C12—C11126.4 (5)C31—C32—C33'107.0 (8)
C17—C12—C11119.4 (5)C27—C32—C33'135.7 (8)
C14—C13—C12122.8 (5)C31—C32—C33135.3 (7)
C14—C13—Cl3116.5 (4)C27—C32—C33108.1 (8)
C12—C13—Cl3120.7 (4)C34—C33—C32119.8 (12)
C13—C14—C15119.8 (5)C34—C33—H33120.1
C13—C14—H14120.1C32—C33—H33120.1
C15—C14—H14120.1C33—C34—C35121.1 (13)
C16—C15—C14120.1 (5)C33—C34—C34ii162.7 (14)
C16—C15—H15119.9C35—C34—C34ii46.9 (6)
C14—C15—H15119.9C33—C34—H34119.4
C15—C16—C17119.7 (5)C35—C34—H34119.4
C15—C16—H16120.1C34ii—C34—H3474.0
C17—C16—H16120.1C34'—C33'—C32119.3 (13)
C16—C17—C12123.4 (5)C34'—C33'—H33'120.3
C16—C17—Cl4117.0 (4)C32—C33'—H33'120.3
C12—C17—Cl4119.5 (4)C33'—C34'—C35122.6 (13)
C19—C18—C23123.0 (5)C33'—C34'—H34'118.7
C19—C18—Cl5118.1 (4)C35—C34'—H34'118.7
C23—C18—Cl5118.9 (4)O3—C35—C34ii136.9 (6)
C20—C19—C18119.7 (5)O3—C35—C34136.9 (6)
C20—C19—H19120.2C34ii—C35—C3486.3 (12)
C18—C19—H19120.2O3—C35—C34'106.4 (6)
C19—C20—C21120.0 (6)O3—C35—C34'ii106.4 (6)
C19—C20—H20120.0C34'—C35—C34'ii147.3 (12)
C21—C20—H20120.0
C6—C1—C2—C31.0 (8)C19—C18—C23—C221.2 (8)
Cl1—C1—C2—C3179.3 (4)Cl5—C18—C23—C22178.9 (4)
C1—C2—C3—C40.6 (9)C19—C18—C23—C24178.3 (5)
C2—C3—C4—C51.7 (9)Cl5—C18—C23—C241.6 (7)
C3—C4—C5—C61.3 (9)C21—C22—C23—C180.9 (8)
C3—C4—C5—Cl2179.1 (4)Cl6—C22—C23—C18176.5 (4)
C2—C1—C6—C51.4 (8)C21—C22—C23—C24178.5 (5)
Cl1—C1—C6—C5179.7 (4)Cl6—C22—C23—C244.1 (8)
C2—C1—C6—C7177.4 (5)C18—C23—C24—C25130.7 (6)
Cl1—C1—C6—C74.3 (7)C22—C23—C24—C2548.8 (9)
C4—C5—C6—C10.3 (8)C23—C24—C25—C26173.8 (4)
Cl2—C5—C6—C1177.5 (4)C24—C25—C26—O24.3 (6)
C4—C5—C6—C7176.0 (5)C24—C25—C26—C25i175.7 (6)
Cl2—C5—C6—C71.7 (8)C32—C27—C28—C292.1 (9)
C1—C6—C7—C8137.8 (6)Cl7—C27—C28—C29178.1 (5)
C5—C6—C7—C846.6 (9)C27—C28—C29—C300.4 (10)
C6—C7—C8—C9179.3 (5)C28—C29—C30—C310.9 (10)
C7—C8—C9—O1175.2 (5)C29—C30—C31—C320.5 (10)
C7—C8—C9—C104.9 (8)C29—C30—C31—Cl8179.9 (5)
O1—C9—C10—C117.4 (8)C30—C31—C32—C271.2 (10)
C8—C9—C10—C11172.7 (5)Cl8—C31—C32—C27178.3 (5)
C9—C10—C11—C12177.0 (5)C30—C31—C32—C33'165.8 (7)
C10—C11—C12—C1332.9 (9)Cl8—C31—C32—C33'14.8 (8)
C10—C11—C12—C17147.6 (6)C30—C31—C32—C33167.2 (9)
C17—C12—C13—C140.3 (8)Cl8—C31—C32—C3312.2 (12)
C11—C12—C13—C14179.9 (5)C28—C27—C32—C312.5 (9)
C17—C12—C13—Cl3177.0 (4)Cl7—C27—C32—C31178.3 (5)
C11—C12—C13—Cl32.5 (7)C28—C27—C32—C33'159.5 (9)
C12—C13—C14—C150.3 (9)Cl7—C27—C32—C33'16.3 (13)
Cl3—C13—C14—C15177.7 (5)C28—C27—C32—C33172.2 (7)
C13—C14—C15—C160.5 (9)Cl7—C27—C32—C3312.0 (8)
C14—C15—C16—C170.1 (9)C31—C32—C33—C3457.6 (17)
C15—C16—C17—C120.6 (9)C27—C32—C33—C34135.7 (13)
C15—C16—C17—Cl4179.9 (5)C32—C33—C34—C35173.8 (9)
C13—C12—C17—C160.8 (7)C32—C33—C34—C34ii132 (4)
C11—C12—C17—C16179.7 (5)C31—C32—C33'—C34'145.2 (11)
C13—C12—C17—Cl4179.9 (4)C27—C32—C33'—C34'51.7 (16)
C11—C12—C17—Cl40.3 (7)C32—C33'—C34'—C35174.9 (9)
C23—C18—C19—C200.5 (9)C33—C34—C35—O315.6 (19)
Cl5—C18—C19—C20179.6 (5)C34ii—C34—C35—O3179.999 (1)
C18—C19—C20—C210.6 (10)C33—C34—C35—C34ii164.4 (19)
C19—C20—C21—C220.9 (10)C33'—C34'—C35—O3178.7 (11)
C20—C21—C22—C230.1 (9)C33'—C34'—C35—C34'ii1.3 (11)
C20—C21—C22—Cl6177.6 (5)
Symmetry codes: (i) x, y+1, z; (ii) x+1/2, y+3/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···Cl30.932.633.160 (6)117
C14—H14···Cl4iii0.932.863.750 (6)162
C25—H25···O3iv0.932.573.444 (8)156
C30—H30···Cl7iii0.932.903.784 (8)159
C34—H34···Cl70.932.913.361 (14)111
Symmetry codes: (iii) x+1/4, y1/4, z1/4; (iv) x1/4, y+5/4, z1/4.
 

Acknowledgements

The authors thank the Central Instrumentation Facility(DST-FIST), Queen Mary's College, Chennai-4 for computing facilities and SAIF, IIT, Madras, for X-ray data collection facilities.

References

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First citationLee, K., Ab Aziz, F. H., Syahida, A., Abas, F., Shaari, K., Israf, D. A. & Lajis, N. H. (2009). Eur. J. Med. Chem. 44, 3195–3200.  Web of Science CrossRef PubMed CAS Google Scholar
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