#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/18/2211850.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2211850
loop_
_publ_author_name
'Ray J. Butcher'
'Yathirajan, H. S.'
'Narayana, B.'
'Mithun, A.'
'Sarojini, B. K.'
_publ_section_title
(2E)-1-(2,4-Dichlorophenyl)-3-[4-(methylsulfanyl)phenyl]prop-2-en-1-one
_journal_coeditor_code           HK2154
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o30
_journal_page_last               o32
_journal_paper_doi               10.1107/S1600536806050069
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C16 H12 Cl2 O S'
_chemical_formula_moiety         'C16 H12 Cl2 O S'
_chemical_formula_sum            'C16 H12 Cl2 O S'
_chemical_formula_weight         323.22
_chemical_name_systematic
;
(2E)-1-(2,4-Dichlorophenyl)-3-[4-(methylsulfanyl)phenyl]prop-2-en-1-one
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 97.736(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.957(3)
_cell_length_b                   3.8920(8)
_cell_length_c                   14.135(3)
_cell_measurement_reflns_used    3886
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      28.10
_cell_measurement_theta_min      2.91
_cell_volume                     706.3(3)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'SMART (Bruker, 2006)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2003)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6061
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.11
_diffrn_reflns_theta_min         1.45
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_T_max  0.9371
_exptl_absorpt_correction_T_min  0.7118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.345
_refine_ls_abs_structure_details 'Flack (1983), with 926 Friedel pairs'
_refine_ls_abs_structure_Flack   0.16(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2893
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0284
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0419P)²+0.1565P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0708
_reflns_number_gt                2811
_reflns_number_total             2893
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2154.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2211850
_cod_database_fobs_code          2211850
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
Cl Cl1 -0.00538(3) 0.37572(13) 0.89930(3) 0.01717(11) Uani d . 1
Cl Cl2 -0.18050(4) -0.19704(15) 0.57168(3) 0.02374(14) Uani d . 1
S S 0.47612(4) 0.18582(14) 1.38761(3) 0.01730(12) Uani d . 1
O O 0.27298(11) 0.4264(5) 0.77095(10) 0.0233(4) Uani d . 1
C C1 0.10934(14) 0.1597(6) 0.76136(12) 0.0142(4) Uani d . 1
C C2 0.01142(14) 0.1855(6) 0.79079(12) 0.0138(4) Uani d . 1
C C3 -0.07867(15) 0.0779(6) 0.73320(13) 0.0164(4) Uani d . 1
H H3A -0.1451 0.1013 0.7539 0.020 Uiso calc R 1
C C4 -0.06879(15) -0.0640(6) 0.64492(12) 0.0159(4) Uani d . 1
C C5 0.02720(14) -0.0971(6) 0.61312(12) 0.0172(4) Uani d . 1
H H5A 0.0328 -0.1983 0.5529 0.021 Uiso calc R 1
C C6 0.11498(15) 0.0205(6) 0.67111(13) 0.0170(4) Uani d . 1
H H6A 0.1808 0.0060 0.6488 0.020 Uiso calc R 1
C C7 0.21045(14) 0.2845(6) 0.81600(12) 0.0160(4) Uani d . 1
C C8 0.23343(14) 0.2203(6) 0.91937(12) 0.0153(4) Uani d . 1
H H8A 0.1887 0.0781 0.9504 0.018 Uiso calc R 1
C C9 0.31791(13) 0.3638(6) 0.96960(12) 0.0145(4) Uani d . 1
H H9A 0.3587 0.5072 0.9348 0.017 Uiso calc R 1
C C10 0.35436(13) 0.3250(6) 1.07136(12) 0.0140(4) Uani d . 1
C C11 0.29612(14) 0.1612(6) 1.13499(13) 0.0160(4) Uani d . 1
H H11A 0.2289 0.0734 1.1123 0.019 Uiso calc R 1
C C12 0.33543(14) 0.1260(6) 1.23055(13) 0.0163(4) Uani d . 1
H H12A 0.2949 0.0155 1.2728 0.020 Uiso calc R 1
C C13 0.43522(14) 0.2531(5) 1.26544(12) 0.0142(4) Uani d . 1
C C14 0.49327(14) 0.4181(6) 1.20340(12) 0.0155(4) Uani d . 1
H H14A 0.5605 0.5057 1.2261 0.019 Uiso calc R 1
C C15 0.45252(14) 0.4548(6) 1.10765(13) 0.0150(4) Uani d . 1
H H15A 0.4924 0.5709 1.0658 0.018 Uiso calc R 1
C C16 0.60977(14) 0.3260(6) 1.40322(13) 0.0188(4) Uani d . 1
H H16A 0.6418 0.2757 1.4686 0.028 Uiso calc R 1
H H16B 0.6125 0.5739 1.3917 0.028 Uiso calc R 1
H H16C 0.6478 0.2047 1.3579 0.028 Uiso calc R 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
_geom_angle_publ_flag
C13 S C16 103.49(9) y
C2 C1 C6 117.58(16) ?
C2 C1 C7 126.01(17) ?
C6 C1 C7 116.34(16) ?
C1 C2 C3 121.96(17) ?
C1 C2 Cl1 121.38(14) ?
C3 C2 Cl1 116.58(14) ?
C4 C3 C2 118.27(17) ?
C4 C3 H3A 120.9 ?
C2 C3 H3A 120.9 ?
C5 C4 C3 121.69(16) ?
C5 C4 Cl2 119.38(14) ?
C3 C4 Cl2 118.92(15) ?
C4 C5 C6 118.58(17) ?
C4 C5 H5A 120.7 ?
C6 C5 H5A 120.7 ?
C5 C6 C1 121.88(17) ?
C5 C6 H6A 119.1 ?
C1 C6 H6A 119.1 ?
O C7 C8 122.12(17) y
O C7 C1 117.89(16) y
C8 C7 C1 119.93(17) y
C9 C8 C7 119.70(18) y
C9 C8 H8A 120.2 ?
C7 C8 H8A 120.2 ?
C8 C9 C10 127.60(18) y
C8 C9 H9A 116.2 ?
C10 C9 H9A 116.2 ?
C15 C10 C11 118.00(16) ?
C15 C10 C9 118.75(17) ?
C11 C10 C9 123.24(17) ?
C12 C11 C10 120.77(18) ?
C12 C11 H11A 119.6 ?
C10 C11 H11A 119.6 ?
C11 C12 C13 120.40(18) ?
C11 C12 H12A 119.8 ?
C13 C12 H12A 119.8 ?
C14 C13 C12 119.39(17) ?
C14 C13 S 124.96(14) ?
C12 C13 S 115.64(14) ?
C13 C14 C15 119.67(17) ?
C13 C14 H14A 120.2 ?
C15 C14 H14A 120.2 ?
C14 C15 C10 121.75(18) ?
C14 C15 H15A 119.1 ?
C10 C15 H15A 119.1 ?
S C16 H16A 109.5 ?
S C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
S C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C2 1.7430(19) y
Cl2 C4 1.7411(19) y
S C13 1.7564(18) y
S C16 1.801(2) y
O C7 1.227(2) y
C1 C2 1.391(2) ?
C1 C6 1.397(3) ?
C1 C7 1.509(2) y
C2 C3 1.395(3) ?
C3 C4 1.386(3) ?
C3 H3A 0.9500 ?
C4 C5 1.384(3) ?
C5 C6 1.387(3) ?
C5 H5A 0.9500 ?
C6 H6A 0.9500 ?
C7 C8 1.473(2) y
C8 C9 1.343(3) y
C8 H8A 0.9500 ?
C9 C10 1.460(2) ?
C9 H9A 0.9500 ?
C10 C15 1.400(3) ?
C10 C11 1.403(3) ?
C11 C12 1.385(2) ?
C11 H11A 0.9500 ?
C12 C13 1.410(3) ?
C12 H12A 0.9500 ?
C13 C14 1.387(3) ?
C14 C15 1.392(2) ?
C14 H14A 0.9500 ?
C15 H15A 0.9500 ?
C16 H16A 0.9800 ?
C16 H16B 0.9800 ?
C16 H16C 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
C16 H16B O 2_657 0.98 3.21 3.852(3) 124.8
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
C6 C1 C2 C3 -0.1(3)
C7 C1 C2 C3 176.7(2)
C6 C1 C2 Cl1 -176.58(16)
C7 C1 C2 Cl1 0.2(3)
C1 C2 C3 C4 1.2(3)
Cl1 C2 C3 C4 177.84(17)
C2 C3 C4 C5 -0.6(3)
C2 C3 C4 Cl2 -179.57(17)
C3 C4 C5 C6 -1.0(3)
Cl2 C4 C5 C6 177.92(17)
C4 C5 C6 C1 2.2(3)
C2 C1 C6 C5 -1.6(3)
C7 C1 C6 C5 -178.8(2)
C2 C1 C7 O -139.1(2)
C6 C1 C7 O 37.8(3)
C2 C1 C7 C8 43.7(3)
C6 C1 C7 C8 -139.5(2)
O C7 C8 C9 10.2(3)
C1 C7 C8 C9 -172.7(2)
C7 C8 C9 C10 -178.69(19)
C8 C9 C10 C15 170.7(2)
C8 C9 C10 C11 -8.8(4)
C15 C10 C11 C12 -0.8(3)
C9 C10 C11 C12 178.8(2)
C10 C11 C12 C13 -0.3(3)
C11 C12 C13 C14 0.9(3)
C11 C12 C13 S -179.15(17)
C16 S C13 C14 -7.2(2)
C16 S C13 C12 172.80(16)
C12 C13 C14 C15 -0.3(3)
S C13 C14 C15 179.74(16)
C13 C14 C15 C10 -0.9(3)
C11 C10 C15 C14 1.4(3)
C9 C10 C15 C14 -178.2(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655136
