#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/86/2208615.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_2208615
loop_
_publ_author_name
'Ray J. Butcher'
'Yathirajan, H. S.'
'Anilkumar, H. G.'
'Sarojini, B. K.'
'Narayana, B.'
_publ_section_title
;
 2-Bromo-1-(4-methylphenyl)-3-[4-(methylsulfanyl)phenyl]prop-2-en-1-one
;
_journal_coeditor_code           HG2019
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1659
_journal_page_last               o1661
_journal_paper_doi               10.1107/S1600536806011160
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C17 H15 Br O S'
_chemical_formula_moiety         'C17 H15 Br O S'
_chemical_formula_sum            'C17 H15 Br O S'
_chemical_formula_weight         347.26
_chemical_name_systematic
;
2-Bromo-1-(4-methylphenyl)-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                 98.291(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.9708(9)
_cell_length_b                   5.5031(6)
_cell_length_c                   16.9923(18)
_cell_measurement_reflns_used    6302
_cell_measurement_temperature    366(2)
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      2.42
_cell_volume                     737.56(14)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.925
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measurement_device_type  'Bruker SMART 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  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0531
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8184
_diffrn_reflns_theta_full        30.75
_diffrn_reflns_theta_max         30.75
_diffrn_reflns_theta_min         2.42
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.920
_exptl_absorpt_correction_T_max  0.482
_exptl_absorpt_correction_T_min  0.230
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.171
_refine_diff_density_min         -0.518
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.029(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         4028
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0238
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0541
_refine_ls_wR_factor_ref         0.0545
_reflns_number_gt                3821
_reflns_number_total             4028
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2019.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2208615
_cod_database_fobs_code          2208615
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
Br Br 0.96840(2) -0.00274(4) 0.775087(9) 0.01950(5) Uani d . 1
S S 0.70913(6) 0.13574(8) 1.17103(3) 0.01365(9) Uani d . 1
O O 0.9237(2) 0.3919(3) 0.64877(8) 0.0249(3) Uani d . 1
C C1 0.5891(3) 0.3869(4) 1.20207(11) 0.0174(4) Uani d . 1
H H1A 0.5657 0.3585 1.2552 0.026 Uiso calc R 1
H H1B 0.4843 0.4019 1.1667 0.026 Uiso calc R 1
H H1C 0.6534 0.5340 1.2009 0.026 Uiso calc R 1
C C2 0.7288(3) 0.2139(3) 1.07225(10) 0.0128(4) Uani d . 1
C C3 0.8147(2) 0.0511(3) 1.02957(11) 0.0147(4) Uani d . 1
H H3A 0.8639 -0.0869 1.0547 0.018 Uiso calc R 1
C C4 0.8282(3) 0.0916(3) 0.94990(11) 0.0150(4) Uani d . 1
H H4A 0.8862 -0.0191 0.9225 0.018 Uiso calc R 1
C C5 0.7544(2) 0.2997(3) 0.91034(11) 0.0129(4) Uani d . 1
C C6 0.6733(2) 0.4639(4) 0.95536(10) 0.0136(4) Uani d . 1
H H6A 0.6263 0.6045 0.9310 0.016 Uiso calc R 1
C C7 0.6604(3) 0.4248(3) 1.03493(11) 0.0144(4) Uani d . 1
H H7A 0.6065 0.5383 1.0632 0.017 Uiso calc R 1
C C8 0.7491(2) 0.3614(3) 0.82629(10) 0.0133(4) Uani d . 1
H H8A 0.6812 0.4957 0.8111 0.016 Uiso calc R 1
C C9 0.8206(3) 0.2674(4) 0.76608(11) 0.0151(4) Uani d . 1
C C10 0.8046(3) 0.3912(4) 0.68660(11) 0.0170(4) Uani d . 1
C C11 0.6408(2) 0.5098(5) 0.65509(9) 0.0138(3) Uani d . 1
C C12 0.4857(3) 0.4050(3) 0.66474(11) 0.0149(4) Uani d . 1
H H12A 0.4840 0.2640 0.6948 0.018 Uiso calc R 1
C C13 0.3341(2) 0.5077(5) 0.63022(9) 0.0164(3) Uani d . 1
H H13A 0.2321 0.4324 0.6359 0.020 Uiso calc R 1
C C14 0.3334(3) 0.7240(4) 0.58690(11) 0.0167(4) Uani d . 1
C C15 0.4891(3) 0.8284(4) 0.57676(11) 0.0172(4) Uani d . 1
H H15A 0.4905 0.9712 0.5476 0.021 Uiso calc R 1
C C16 0.6410(3) 0.7230(4) 0.60942(11) 0.0158(4) Uani d . 1
H H16A 0.7432 0.7932 0.6012 0.019 Uiso calc R 1
C C17 0.1689(3) 0.8443(5) 0.55354(12) 0.0253(5) Uani d . 1
H H17A 0.0765 0.7352 0.5576 0.038 Uiso calc R 1
H H17B 0.1707 0.8848 0.4987 0.038 Uiso calc R 1
H H17C 0.1544 0.9897 0.5831 0.038 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'
Br Br -0.2901 2.4595 '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
C2 S C1 102.45(9) y
S C1 H1A 109.5 ?
S C1 H1B 109.5 ?
H1A C1 H1B 109.5 ?
S C1 H1C 109.5 ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
C3 C2 C7 119.17(16) ?
C3 C2 S 117.20(14) ?
C7 C2 S 123.61(14) ?
C4 C3 C2 121.06(17) ?
C4 C3 H3A 119.5 ?
C2 C3 H3A 119.5 ?
C3 C4 C5 120.53(17) ?
C3 C4 H4A 119.7 ?
C5 C4 H4A 119.7 ?
C6 C5 C4 117.16(16) ?
C6 C5 C8 115.64(16) ?
C4 C5 C8 127.18(17) ?
C7 C6 C5 122.46(18) ?
C7 C6 H6A 118.8 ?
C5 C6 H6A 118.8 ?
C6 C7 C2 119.55(17) ?
C6 C7 H7A 120.2 ?
C2 C7 H7A 120.2 ?
C9 C8 C5 134.27(18) ?
C9 C8 H8A 112.9 ?
C5 C8 H8A 112.9 ?
C8 C9 C10 121.31(18) ?
C8 C9 Br 124.68(15) y
C10 C9 Br 113.62(13) y
O C10 C11 121.15(17) y
O C10 C9 120.26(19) y
C11 C10 C9 118.59(17) ?
C12 C11 C16 118.78(18) ?
C12 C11 C10 121.5(2) ?
C16 C11 C10 119.55(18) ?
C13 C12 C11 120.99(19) ?
C13 C12 H12A 119.5 ?
C11 C12 H12A 119.5 ?
C12 C13 C14 120.48(19) ?
C12 C13 H13A 119.8 ?
C14 C13 H13A 119.8 ?
C13 C14 C15 118.51(18) ?
C13 C14 C17 120.65(19) ?
C15 C14 C17 120.83(19) ?
C16 C15 C14 121.20(18) ?
C16 C15 H15A 119.4 ?
C14 C15 H15A 119.4 ?
C15 C16 C11 119.99(19) ?
C15 C16 H16A 120.0 ?
C11 C16 H16A 120.0 ?
C14 C17 H17A 109.5 ?
C14 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
C14 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br C9 1.889(2) y
S C2 1.7613(18) y
S C1 1.803(2) y
O C10 1.220(2) y
C1 H1A 0.9600 ?
C1 H1B 0.9600 ?
C1 H1C 0.9600 ?
C2 C3 1.393(2) ?
C2 C7 1.395(3) ?
C3 C4 1.391(3) ?
C3 H3A 0.9300 ?
C4 C5 1.412(3) ?
C4 H4A 0.9300 ?
C5 C6 1.401(3) ?
C5 C8 1.463(2) y
C6 C7 1.388(2) ?
C6 H6A 0.9300 ?
C7 H7A 0.9300 ?
C8 C9 1.344(2) y
C8 H8A 0.9300 ?
C9 C10 1.502(3) y
C10 C11 1.489(3) y
C11 C12 1.395(3) ?
C11 C16 1.407(3) ?
C12 C13 1.385(3) ?
C12 H12A 0.9300 ?
C13 C14 1.399(3) ?
C13 H13A 0.9300 ?
C14 C15 1.401(3) ?
C14 C17 1.505(3) ?
C15 C16 1.385(3) ?
C15 H15A 0.9300 ?
C16 H16A 0.9300 ?
C17 H17A 0.9600 ?
C17 H17B 0.9600 ?
C17 H17C 0.9600 ?
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
C13 H13A O 1_455 0.93 2.51 3.392(2) 158.6
C17 H17B O 2_656 0.96 2.51 3.420(3) 158.1
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
C1 S C2 C3 -178.89(16)
C1 S C2 C7 -0.30(19)
C7 C2 C3 C4 -2.2(3)
S C2 C3 C4 176.44(16)
C2 C3 C4 C5 -0.1(3)
C3 C4 C5 C6 2.0(3)
C3 C4 C5 C8 -176.37(19)
C4 C5 C6 C7 -1.7(3)
C8 C5 C6 C7 176.86(18)
C5 C6 C7 C2 -0.6(3)
C3 C2 C7 C6 2.5(3)
S C2 C7 C6 -176.05(15)
C6 C5 C8 C9 173.5(2)
C4 C5 C8 C9 -8.1(4)
C5 C8 C9 C10 -173.3(2)
C5 C8 C9 Br -0.9(3)
C8 C9 C10 O 142.4(2)
Br C9 C10 O -30.8(3)
C8 C9 C10 C11 -38.2(3)
Br C9 C10 C11 148.63(16)
O C10 C11 C12 140.4(2)
C9 C10 C11 C12 -39.0(3)
O C10 C11 C16 -34.8(3)
C9 C10 C11 C16 145.81(18)
C16 C11 C12 C13 0.0(3)
C10 C11 C12 C13 -175.25(18)
C11 C12 C13 C14 -2.1(3)
C12 C13 C14 C15 2.4(3)
C12 C13 C14 C17 -176.25(18)
C13 C14 C15 C16 -0.7(3)
C17 C14 C15 C16 177.91(18)
C14 C15 C16 C11 -1.3(3)
C12 C11 C16 C15 1.7(3)
C10 C11 C16 C15 177.00(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21179537
