##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'PLATON <TABLE ACC> option'
_journal_date_recd_electronic     2016-12-23
_journal_date_accepted     2016-12-28
_journal_name_full     'IUCrData'
_journal_year     2017
_journal_volume     2
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314616020563
_journal_coeditor_code     SU4118
_publ_contact_author_name     'Dr. Manjunath, H. R.'
_publ_contact_author_address
;
Department of Physics
Acharya Institute of Technology
Soldevanahalli
Bengaluru 560 107
India
;
_publ_contact_author_email
                        'manjunathhr@acharya.ac.in, naveen@ioe.uni-mysore.ac.in'
_publ_contact_author_fax     '+91 821 2419485'
_publ_contact_author_phone     '+91 9886464177'
_publ_section_title
;
(E)-3-(2,3-Dichlorophenyl)-1-(2-methoxyphenyl)prop-2-en-1-one
;
loop_
    _publ_author_name
    _publ_author_address
    'Sunitha, V. M.'
;
Department of Physics,
Shri Pillappa College of Engineering,
Bengaluru 560 089, India
Department of Physics,
Prist University, Vallam,
Tanjavur 513 403, India
;
    'Naveen, S.'
;
Institution of Excellence,
University of Mysore,
Manasagangotri,
Mysuru 570 006, India
;
    'Vagish, C. B.'
;
Department of Chemistry,
Yuvaraja's College
University of Mysore,
Mysuru 570 005, India
;
    'Ajay Kumar, K.'
;
Department of Chemistry,
Yuvaraja's College
University of Mysore,
Mysuru 570 005, India
;
    'Lokanath, N. K.'
;
Department of Studies in Physics,
University of Mysore,
Manasagangotri,
Mysuru 570 006, India
;
    'Manjunath, H. R.'
;
Department of Physics
Acharya Institute of Technology
Soldevanahalli
Bengaluru 560 107
India
;
_publ_section_synopsis
;
In the crystal of the title chalcone derivative, molecules are linked
via weak C---H...O hydrogen bonds, forming zigzag chains along the
c axis.
;
data_I
_chemical_name_systematic
;
(E)-3-(2,3-Dichlorophenyl)-1-(2-methoxyphenyl)prop-2-en-1-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H12 Cl2 O2'
_chemical_formula_sum     'C16 H12 Cl2 O2'
_chemical_formula_structural     ?
_chemical_formula_iupac     'C16 H12 Cl2 O2'
_chemical_formula_weight     307.16
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P n a 21'
_symmetry_space_group_name_Hall     'P 2c -2n'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 -x,-y,1/2+z
    3 1/2-x,1/2+y,1/2+z
    4 1/2+x,1/2-y,z
_cell_length_a     24.7531(9)
_cell_length_b     3.9036(2)
_cell_length_c     14.3360(6)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1385.23(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1893
_cell_measurement_theta_min     3.57
_cell_measurement_theta_max     64.64
_cell_measurement_temperature     296
_cell_special_details
;
;
_exptl_crystal_description     'block'
_exptl_crystal_colour     'Yellow'
_exptl_crystal_size_max     0.28
_exptl_crystal_size_mid     0.26
_exptl_crystal_size_min     0.25
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.473
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'Not Measured'
_exptl_crystal_F_000     632
_exptl_absorpt_coefficient_mu     4.197
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_absorpt_correction_T_min     0.386
_exptl_absorpt_correction_T_max     0.420
_exptl_special_details
;
;
_diffrn_ambient_temperature     296
_diffrn_radiation_type     'CuK\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source     'Bruker MicroStar microfocus rotating anode'
_diffrn_radiation_monochromator     'Helios multilayer optics'
_diffrn_measurement_device_type     'Bruker X8 Proteum'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     18.4
_diffrn_reflns_number     7897
_diffrn_reflns_av_R_equivalents     0.0674
_diffrn_reflns_av_sigmaI/netI     0.0840
_diffrn_reflns_theta_min     3.57
_diffrn_reflns_theta_max     64.64
_diffrn_reflns_theta_full     64.64
_diffrn_measured_fraction_theta_max     0.979
_diffrn_measured_fraction_theta_full     0.979
_diffrn_reflns_limit_h_min     -28
_diffrn_reflns_limit_h_max     27
_diffrn_reflns_limit_k_min     -4
_diffrn_reflns_limit_k_max     4
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_diffrn_reflns_reduction_process
;
;
_refine_special_details
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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.
;
_reflns_number_total     2175
_reflns_number_gt     1893
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0584
_refine_ls_R_factor_gt     0.0485
_refine_ls_wR_factor_gt     0.1209
_refine_ls_wR_factor_ref     0.1267
_refine_ls_goodness_of_fit_ref     1.027
_refine_ls_restrained_S_all     1.027
_refine_ls_number_reflns     2175
_refine_ls_number_parameters     182
_refine_ls_number_restraints     1
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0694P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.331
_refine_diff_density_min     -0.366
_refine_ls_extinction_method     'none'
_refine_ls_abs_structure_details
;
971 (86%) Friedel pairs; Flack (1983)
;
_refine_ls_abs_structure_Flack     0.03(2)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C C 0.0181 0.0091 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    H H 0.0000 0.0000 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    Cl Cl 0.3639 0.7018 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    O O 0.0492 0.0322 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 0.80662(4) 1.1660(3) 0.33612(8) 0.0407(3) Uani d . 1.000 . .
    Cl Cl2 0.69437(4) 0.8842(3) 0.26987(7) 0.0381(3) Uani d . 1.000 . .
    O O1 0.51800(11) 0.4104(7) 0.3625(2) 0.0379(10) Uani d . 1.000 . .
    O O2 0.55245(10) 0.1930(7) 0.6377(2) 0.0327(8) Uani d . 1.000 . .
    C C1 0.70987(16) 0.8885(10) 0.3882(3) 0.0287(12) Uani d . 1.000 . .
    C C2 0.67209(15) 0.7666(10) 0.4528(3) 0.0285(11) Uani d . 1.000 . .
    C C3 0.68707(15) 0.7817(13) 0.5468(3) 0.0328(11) Uani d . 1.000 . .
    C C4 0.73578(17) 0.9109(11) 0.5754(3) 0.0363(14) Uani d . 1.000 . .
    C C5 0.77279(16) 1.0284(11) 0.5106(3) 0.0357(14) Uani d . 1.000 . .
    C C6 0.75962(15) 1.0168(11) 0.4167(3) 0.0318(11) Uani d . 1.000 . .
    C C7 0.62046(16) 0.6269(10) 0.4238(3) 0.0307(12) Uani d . 1.000 . .
    C C8 0.57938(16) 0.5491(11) 0.4795(3) 0.0315(11) Uani d . 1.000 . .
    C C9 0.52915(15) 0.3920(10) 0.4451(3) 0.0277(11) Uani d . 1.000 . .
    C C10 0.49098(15) 0.2178(9) 0.5104(3) 0.0266(11) Uani d . 1.000 . .
    C C11 0.44040(15) 0.1365(10) 0.4748(3) 0.0313(11) Uani d . 1.000 . .
    C C12 0.40200(15) -0.0369(10) 0.5257(3) 0.0352(13) Uani d . 1.000 . .
    C C13 0.41414(17) -0.1308(10) 0.6165(3) 0.0383(14) Uani d . 1.000 . .
    C C14 0.46347(17) -0.0531(11) 0.6552(3) 0.0360(12) Uani d . 1.000 . .
    C C15 0.50218(16) 0.1218(9) 0.6032(3) 0.0291(11) Uani d . 1.000 . .
    C C16 0.56561(19) 0.0802(11) 0.7298(3) 0.0373(14) Uani d . 1.000 . .
    H H3 0.66300 0.70090 0.59150 0.0390 Uiso c R 1.000 . .
    H H4 0.74400 0.91970 0.63870 0.0440 Uiso c R 1.000 . .
    H H5 0.80600 1.11400 0.52980 0.0430 Uiso c R 1.000 . .
    H H7 0.61570 0.58820 0.36030 0.0370 Uiso c R 1.000 . .
    H H8 0.58250 0.59580 0.54290 0.0380 Uiso c R 1.000 . .
    H H11 0.43210 0.20190 0.41410 0.0370 Uiso c R 1.000 . .
    H H12 0.36860 -0.09000 0.49960 0.0420 Uiso c R 1.000 . .
    H H13 0.38860 -0.24780 0.65180 0.0460 Uiso c R 1.000 . .
    H H14 0.47100 -0.11760 0.71620 0.0430 Uiso c R 1.000 . .
    H H16A 0.54100 0.18170 0.77370 0.0560 Uiso c R 1.000 . .
    H H16B 0.60190 0.14790 0.74470 0.0560 Uiso c R 1.000 . .
    H H16C 0.56270 -0.16480 0.73300 0.0560 Uiso c R 1.000 . .
_geom_special_details
;
 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 esds are taken into account in the estimation of
 distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Cl1 C6 . . 1.740(4) no
    Cl2 C1 . . 1.739(4) no
    O1 C9 . . 1.218(5) no
    O2 C15 . . 1.368(5) no
    O2 C16 . . 1.429(5) no
    C1 C2 . . 1.400(6) no
    C1 C6 . . 1.391(6) no
    C2 C3 . . 1.399(6) no
    C2 C7 . . 1.450(5) no
    C3 C4 . . 1.370(6) no
    C4 C5 . . 1.383(6) no
    C5 C6 . . 1.386(6) no
    C7 C8 . . 1.328(6) no
    C8 C9 . . 1.472(6) no
    C9 C10 . . 1.494(6) no
    C10 C11 . . 1.389(5) no
    C10 C15 . . 1.410(6) no
    C11 C12 . . 1.376(6) no
    C12 C13 . . 1.385(6) no
    C13 C14 . . 1.375(6) no
    C14 C15 . . 1.393(6) no
    C3 H3 . . 0.9300 no
    C4 H4 . . 0.9300 no
    C5 H5 . . 0.9300 no
    C7 H7 . . 0.9300 no
    C8 H8 . . 0.9300 no
    C11 H11 . . 0.9300 no
    C12 H12 . . 0.9300 no
    C13 H13 . . 0.9300 no
    C14 H14 . . 0.9300 no
    C16 H16A . . 0.9600 no
    C16 H16B . . 0.9600 no
    C16 H16C . . 0.9600 no
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C15 O2 C16 . . . 118.6(3) no
    Cl2 C1 C2 . . . 119.7(3) no
    Cl2 C1 C6 . . . 119.0(3) no
    C2 C1 C6 . . . 121.3(4) no
    C1 C2 C3 . . . 116.5(4) no
    C1 C2 C7 . . . 121.8(4) no
    C3 C2 C7 . . . 121.7(4) no
    C2 C3 C4 . . . 122.5(4) no
    C3 C4 C5 . . . 120.3(4) no
    C4 C5 C6 . . . 119.1(4) no
    Cl1 C6 C1 . . . 121.2(3) no
    Cl1 C6 C5 . . . 118.5(3) no
    C1 C6 C5 . . . 120.4(4) no
    C2 C7 C8 . . . 126.0(4) no
    C7 C8 C9 . . . 122.7(4) no
    O1 C9 C8 . . . 119.5(4) no
    O1 C9 C10 . . . 119.5(3) no
    C8 C9 C10 . . . 120.9(4) no
    C9 C10 C11 . . . 116.4(4) no
    C9 C10 C15 . . . 126.0(3) no
    C11 C10 C15 . . . 117.6(4) no
    C10 C11 C12 . . . 122.7(4) no
    C11 C12 C13 . . . 118.6(4) no
    C12 C13 C14 . . . 120.9(4) no
    C13 C14 C15 . . . 120.2(4) no
    O2 C15 C10 . . . 117.8(3) no
    O2 C15 C14 . . . 122.1(4) no
    C10 C15 C14 . . . 120.0(4) no
    C2 C3 H3 . . . 119.00 no
    C4 C3 H3 . . . 119.00 no
    C3 C4 H4 . . . 120.00 no
    C5 C4 H4 . . . 120.00 no
    C4 C5 H5 . . . 120.00 no
    C6 C5 H5 . . . 121.00 no
    C2 C7 H7 . . . 117.00 no
    C8 C7 H7 . . . 117.00 no
    C7 C8 H8 . . . 119.00 no
    C9 C8 H8 . . . 119.00 no
    C10 C11 H11 . . . 119.00 no
    C12 C11 H11 . . . 119.00 no
    C11 C12 H12 . . . 121.00 no
    C13 C12 H12 . . . 121.00 no
    C12 C13 H13 . . . 120.00 no
    C14 C13 H13 . . . 120.00 no
    C13 C14 H14 . . . 120.00 no
    C15 C14 H14 . . . 120.00 no
    O2 C16 H16A . . . 109.00 no
    O2 C16 H16B . . . 110.00 no
    O2 C16 H16C . . . 110.00 no
    H16A C16 H16B . . . 109.00 no
    H16A C16 H16C . . . 109.00 no
    H16B C16 H16C . . . 109.00 no
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C16 O2 C15 C10 . . . . -176.5(3) no
    C16 O2 C15 C14 . . . . 0.7(5) no
    Cl2 C1 C2 C3 . . . . -179.3(3) no
    Cl2 C1 C2 C7 . . . . 1.7(5) no
    C6 C1 C2 C3 . . . . 0.1(6) no
    C6 C1 C2 C7 . . . . -178.9(4) no
    Cl2 C1 C6 Cl1 . . . . -1.0(5) no
    Cl2 C1 C6 C5 . . . . 179.0(3) no
    C2 C1 C6 Cl1 . . . . 179.7(3) no
    C2 C1 C6 C5 . . . . -0.4(6) no
    C1 C2 C3 C4 . . . . 0.6(7) no
    C7 C2 C3 C4 . . . . 179.6(4) no
    C1 C2 C7 C8 . . . . -170.2(4) no
    C3 C2 C7 C8 . . . . 10.8(7) no
    C2 C3 C4 C5 . . . . -1.0(7) no
    C3 C4 C5 C6 . . . . 0.7(7) no
    C4 C5 C6 Cl1 . . . . 180.0(3) no
    C4 C5 C6 C1 . . . . 0.0(6) no
    C2 C7 C8 C9 . . . . -176.9(4) no
    C7 C8 C9 O1 . . . . -19.3(6) no
    C7 C8 C9 C10 . . . . 162.3(4) no
    O1 C9 C10 C11 . . . . -10.4(5) no
    O1 C9 C10 C15 . . . . 167.8(4) no
    C8 C9 C10 C11 . . . . 168.1(4) no
    C8 C9 C10 C15 . . . . -13.7(6) no
    C9 C10 C11 C12 . . . . 177.2(4) no
    C15 C10 C11 C12 . . . . -1.2(6) no
    C9 C10 C15 O2 . . . . 0.0(6) no
    C9 C10 C15 C14 . . . . -177.2(4) no
    C11 C10 C15 O2 . . . . 178.3(3) no
    C11 C10 C15 C14 . . . . 1.0(5) no
    C10 C11 C12 C13 . . . . 0.7(6) no
    C11 C12 C13 C14 . . . . 0.0(6) no
    C12 C13 C14 C15 . . . . -0.1(6) no
    C13 C14 C15 O2 . . . . -177.5(4) no
    C13 C14 C15 C10 . . . . -0.4(6) no
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    C14 H14 O1 2_655 0.93 2.40 3.315(5) 167 yes
    C16 H16A O1 2_665 0.96 2.51 3.443(5) 164 yes
