#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/78/2227827.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227827
loop_
_publ_author_name
'Harrison, William T. A.'
'Chidan Kumar, C. S.'
'Yathirajan, H. S.'
'Mayekar, A. N.'
'Narayana, B.'
_publ_section_title
;
 (E)-1-(2,5-Dichloro-3-thienyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one
;
_journal_coeditor_code           NG5014
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2479
_journal_paper_doi               10.1107/S1600536810035142
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H12 Cl2 O3 S'
_chemical_formula_moiety         'C15 H12 Cl2 O3 S'
_chemical_formula_sum            'C15 H12 Cl2 O3 S'
_chemical_formula_weight         343.21
_chemical_name_systematic
;
(E)-1-(2,5-Dichloro-3-thienyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.1810(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9331(2)
_cell_length_b                   8.9997(2)
_cell_length_c                   18.8210(5)
_cell_measurement_reflns_used    20728
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1489.29(6)
_computing_cell_refinement       'COLLECT (Nonius, 1998)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'DENZO (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 ( Farrugia (1997)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22032
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         3.16
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.582
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '[SADABS (Bruker, 2003) and Blessing (1995)]'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.719
_refine_diff_density_min         -0.413
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3424
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0482
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0340P)²+1.9239P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1125
_reflns_number_gt                2834
_reflns_number_total             3424
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng5014.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2227827
_cod_database_fobs_code          2227827
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4943(3) 0.2226(3) 0.72975(12) 0.0218(5) Uani d . 1 . .
C C2 0.5681(3) 0.2506(3) 0.67246(14) 0.0253(5) Uani d . 1 . .
H H2 0.6632 0.2050 0.6705 0.030 Uiso calc R 1 . .
C C3 0.5013(3) 0.3471(3) 0.61723(14) 0.0273(5) Uani d . 1 . .
H H3 0.5512 0.3644 0.5774 0.033 Uiso calc R 1 . .
C C4 0.3644(3) 0.4175(3) 0.61939(13) 0.0248(5) Uani d . 1 . .
C C5 0.2908(3) 0.3901(3) 0.67817(13) 0.0227(5) Uani d . 1 . .
H H5 0.1977 0.4388 0.6809 0.027 Uiso calc R 1 . .
C C6 0.3533(3) 0.2927(3) 0.73192(12) 0.0207(5) Uani d . 1 . .
C C7 0.2948(3) 0.5123(3) 0.55890(14) 0.0269(5) Uani d . 1 . .
H H7 0.3459 0.5142 0.5187 0.032 Uiso calc R 1 . .
C C8 0.1686(3) 0.5971(3) 0.55235(13) 0.0232(5) Uani d . 1 . .
H H8 0.1154 0.6027 0.5918 0.028 Uiso calc R 1 . .
C C9 0.1115(3) 0.6799(3) 0.48719(13) 0.0230(5) Uani d . 1 . .
C C10 -0.0865(3) 0.8706(3) 0.43372(13) 0.0217(5) Uani d . 1 . .
C C11 -0.0291(3) 0.7698(3) 0.48589(12) 0.0213(5) Uani d . 1 . .
C C12 -0.1241(3) 0.7591(3) 0.53941(13) 0.0265(5) Uani d . 1 . .
H H12 -0.1035 0.6955 0.5803 0.032 Uiso calc R 1 . .
C C13 -0.2457(3) 0.8490(3) 0.52538(14) 0.0298(6) Uani d . 1 . .
C C14 0.6852(3) 0.0533(3) 0.78546(16) 0.0382(7) Uani d . 1 . .
H H14A 0.7073 -0.0128 0.8274 0.057 Uiso calc R 1 . .
H H14B 0.7672 0.1264 0.7875 0.057 Uiso calc R 1 . .
H H14C 0.6776 -0.0053 0.7411 0.057 Uiso calc R 1 . .
C C15 0.1441(3) 0.3186(3) 0.79360(15) 0.0317(6) Uani d . 1 . .
H H15A 0.1087 0.2819 0.8368 0.047 Uiso calc R 1 . .
H H15B 0.0709 0.2905 0.7505 0.047 Uiso calc R 1 . .
H H15C 0.1532 0.4270 0.7960 0.047 Uiso calc R 1 . .
O O1 0.5440(2) 0.1289(2) 0.78610(9) 0.0284(4) Uani d . 1 . .
O O2 0.28886(19) 0.25494(19) 0.78990(9) 0.0265(4) Uani d . 1 . .
O O3 0.1727(2) 0.6738(2) 0.43354(10) 0.0417(5) Uani d . 1 . .
S S1 -0.25196(7) 0.95280(7) 0.44816(4) 0.02811(19) Uani d . 1 . .
Cl Cl1 -0.01562(8) 0.92675(7) 0.35926(3) 0.03212(19) Uani d . 1 . .
Cl Cl2 -0.38786(8) 0.86816(11) 0.57543(4) 0.0513(3) Uani d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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_3
_geom_angle
_geom_angle_publ_flag
O1 C1 C2 . . 125.7(2) ?
O1 C1 C6 . . 114.9(2) ?
C2 C1 C6 . . 119.4(2) ?
C1 C2 C3 . . 119.4(2) ?
C1 C2 H2 . . 120.3 ?
C3 C2 H2 . . 120.3 ?
C4 C3 C2 . . 121.5(2) ?
C4 C3 H3 . . 119.2 ?
C2 C3 H3 . . 119.2 ?
C3 C4 C5 . . 118.8(2) ?
C3 C4 C7 . . 119.9(2) ?
C5 C4 C7 . . 121.3(2) ?
C6 C5 C4 . . 120.3(2) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
O2 C6 C5 . . 124.9(2) ?
O2 C6 C1 . . 114.6(2) ?
C5 C6 C1 . . 120.6(2) ?
C8 C7 C4 . . 129.2(2) ?
C8 C7 H7 . . 115.4 ?
C4 C7 H7 . . 115.4 ?
C7 C8 C9 . . 122.1(2) ?
C7 C8 H8 . . 118.9 ?
C9 C8 H8 . . 118.9 ?
O3 C9 C8 . . 122.1(2) ?
O3 C9 C11 . . 120.4(2) ?
C8 C9 C11 . . 117.5(2) ?
C11 C10 Cl1 . . 129.58(18) ?
C11 C10 S1 . . 113.31(18) ?
Cl1 C10 S1 . . 117.10(14) ?
C10 C11 C12 . . 110.9(2) ?
C10 C11 C9 . . 125.4(2) ?
C12 C11 C9 . . 123.7(2) ?
C13 C12 C11 . . 112.4(2) ?
C13 C12 H12 . . 123.8 ?
C11 C12 H12 . . 123.8 ?
C12 C13 Cl2 . . 127.1(2) ?
C12 C13 S1 . . 113.43(19) ?
Cl2 C13 S1 . . 119.47(16) ?
O1 C14 H14A . . 109.5 ?
O1 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
O1 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
O2 C15 H15A . . 109.5 ?
O2 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O2 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C1 O1 C14 . . 116.9(2) ?
C6 O2 C15 . . 116.97(19) ?
C10 S1 C13 . . 89.97(12) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 . 1.367(3) ?
C1 C2 . 1.383(3) ?
C1 C6 . 1.415(3) ?
C2 C3 . 1.404(4) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.385(4) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.405(3) ?
C4 C7 . 1.470(3) ?
C5 C6 . 1.380(3) ?
C5 H5 . 0.9500 ?
C6 O2 . 1.364(3) ?
C7 C8 . 1.348(3) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.448(3) ?
C8 H8 . 0.9500 ?
C9 O3 . 1.231(3) ?
C9 C11 . 1.491(3) ?
C10 C11 . 1.368(3) ?
C10 Cl1 . 1.713(2) ?
C10 S1 . 1.717(2) ?
C11 C12 . 1.430(3) ?
C12 C13 . 1.343(4) ?
C12 H12 . 0.9500 ?
C13 Cl2 . 1.718(3) ?
C13 S1 . 1.720(3) ?
C14 O1 . 1.435(3) ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
C15 O2 . 1.427(3) ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
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
C3 H3 O3 3_666 0.95 2.53 3.227(3) 130
C12 H12 O1 2_556 0.95 2.55 3.441(3) 157
C14 H14A O3 4_666 0.98 2.53 3.474(3) 161
C15 H15B Cl1 3_566 0.98 2.82 3.647(3) 142
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
O1 C1 C2 C3 . . . . 178.3(2) ?
C6 C1 C2 C3 . . . . -0.5(4) ?
C1 C2 C3 C4 . . . . 1.3(4) ?
C2 C3 C4 C5 . . . . -0.5(4) ?
C2 C3 C4 C7 . . . . -177.2(2) ?
C3 C4 C5 C6 . . . . -1.1(4) ?
C7 C4 C5 C6 . . . . 175.6(2) ?
C4 C5 C6 O2 . . . . -177.8(2) ?
C4 C5 C6 C1 . . . . 1.9(4) ?
O1 C1 C6 O2 . . . . -0.3(3) ?
C2 C1 C6 O2 . . . . 178.7(2) ?
O1 C1 C6 C5 . . . . 179.9(2) ?
C2 C1 C6 C5 . . . . -1.1(3) ?
C3 C4 C7 C8 . . . . -175.4(3) ?
C5 C4 C7 C8 . . . . 8.0(4) ?
C4 C7 C8 C9 . . . . -177.4(2) ?
C7 C8 C9 O3 . . . . 2.2(4) ?
C7 C8 C9 C11 . . . . 179.9(2) ?
Cl1 C10 C11 C12 . . . . 178.78(19) ?
S1 C10 C11 C12 . . . . 0.2(3) ?
Cl1 C10 C11 C9 . . . . -2.3(4) ?
S1 C10 C11 C9 . . . . 179.10(19) ?
O3 C9 C11 C10 . . . . -12.1(4) ?
C8 C9 C11 C10 . . . . 170.1(2) ?
O3 C9 C11 C12 . . . . 166.6(3) ?
C8 C9 C11 C12 . . . . -11.1(4) ?
C10 C11 C12 C13 . . . . 0.4(3) ?
C9 C11 C12 C13 . . . . -178.6(2) ?
C11 C12 C13 Cl2 . . . . 179.3(2) ?
C11 C12 C13 S1 . . . . -0.8(3) ?
C2 C1 O1 C14 . . . . 0.1(4) ?
C6 C1 O1 C14 . . . . 178.9(2) ?
C5 C6 O2 C15 . . . . 1.8(3) ?
C1 C6 O2 C15 . . . . -178.0(2) ?
C11 C10 S1 C13 . . . . -0.5(2) ?
Cl1 C10 S1 C13 . . . . -179.29(16) ?
C12 C13 S1 C10 . . . . 0.7(2) ?
Cl2 C13 S1 C10 . . . . -179.34(18) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 22844563
