#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/06/2230652.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_2230652
loop_
_publ_author_name
'Yaeghoobi, Marzieh'
'Khaledi, Hamid'
'Abdullah, Zanariah'
'Abd.Rahman, Noorsaadah'
_publ_section_title
;
 3-(2-Aminophenylsulfanyl)-1,3-diphenylpropan-1-one
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1693
_journal_paper_doi               10.1107/S1600536811022112
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C21 H19 N O S'
_chemical_formula_moiety         'C21 H19 N O S'
_chemical_formula_sum            'C21 H19 N O S'
_chemical_formula_weight         333.43
_chemical_name_systematic
;
3-(2-Aminophenylsulfanyl)-1,3-diphenylpropan-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                 95.266(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1741(16)
_cell_length_b                   5.6788(8)
_cell_length_c                   27.308(4)
_cell_measurement_reflns_used    713
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.57
_cell_measurement_theta_min      3.03
_cell_volume                     1725.5(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0648
_diffrn_reflns_av_sigmaI/netI    0.0917
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            7303
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  0.9961
_exptl_absorpt_correction_T_min  0.9659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.229
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3195
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.1233
_refine_ls_R_factor_gt           0.0568
_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)+(0.0336P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.1008
_reflns_number_gt                1784
_reflns_number_total             3195
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            go2015.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2230652
_cod_database_fobs_code          2230652
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.80339(6) 0.87951(14) 0.18814(3) 0.0447(2) Uani d . 1 1 . .
O O1 1.0501(2) 0.3126(4) 0.13496(8) 0.0647(7) Uani d . 1 1 . .
N N1 0.6375(2) 0.4530(5) 0.18086(10) 0.0544(8) Uani d . 1 1 . .
H H1A 0.684(3) 0.492(5) 0.2078(11) 0.065 Uiso d . 1 1 . .
H H1B 0.576(3) 0.353(5) 0.1859(10) 0.065 Uiso d . 1 1 . .
C C1 1.0977(3) 0.7137(6) 0.03620(11) 0.0486(8) Uani d . 1 1 . .
H H1 1.0485 0.8384 0.0436 0.058 Uiso calc R 1 1 . .
C C2 1.1576(3) 0.7203(6) -0.00593(11) 0.0583(9) Uani d . 1 1 . .
H H2 1.1483 0.8497 -0.0268 0.070 Uiso calc R 1 1 . .
C C3 1.2307(3) 0.5382(7) -0.01713(11) 0.0576(10) Uani d . 1 1 . .
H H3 1.2698 0.5429 -0.0457 0.069 Uiso calc R 1 1 . .
C C4 1.2458(3) 0.3503(6) 0.01372(11) 0.0567(9) Uani d . 1 1 . .
H H4 1.2970 0.2285 0.0065 0.068 Uiso calc R 1 1 . .
C C5 1.1859(2) 0.3390(5) 0.05554(10) 0.0479(8) Uani d . 1 1 . .
H H5 1.1957 0.2084 0.0761 0.057 Uiso calc R 1 1 . .
C C6 1.1110(2) 0.5215(5) 0.06716(10) 0.0372(7) Uani d . 1 1 . .
C C7 1.0446(3) 0.4961(6) 0.11240(11) 0.0421(8) Uani d . 1 1 . .
C C8 0.9699(2) 0.7008(5) 0.12804(9) 0.0407(8) Uani d . 1 1 . .
H H8A 0.9049 0.7301 0.1027 0.049 Uiso calc R 1 1 . .
H H8B 1.0198 0.8409 0.1310 0.049 Uiso calc R 1 1 . .
C C9 0.9174(2) 0.6565(5) 0.17669(9) 0.0389(7) Uani d . 1 1 . .
H H9 0.8789 0.5013 0.1753 0.047 Uiso calc R 1 1 . .
C C10 1.0071(2) 0.6649(5) 0.22161(9) 0.0330(7) Uani d . 1 1 . .
C C11 1.0841(2) 0.8534(5) 0.23096(10) 0.0397(7) Uani d . 1 1 . .
H H11 1.0841 0.9755 0.2083 0.048 Uiso calc R 1 1 . .
C C12 1.1609(2) 0.8630(6) 0.27341(11) 0.0484(8) Uani d . 1 1 . .
H H12 1.2120 0.9912 0.2792 0.058 Uiso calc R 1 1 . .
C C13 1.1620(3) 0.6835(6) 0.30718(11) 0.0511(9) Uani d . 1 1 . .
H H13 1.2142 0.6889 0.3357 0.061 Uiso calc R 1 1 . .
C C14 1.0852(3) 0.4954(6) 0.29848(11) 0.0502(9) Uani d . 1 1 . .
H H14 1.0850 0.3743 0.3214 0.060 Uiso calc R 1 1 . .
C C15 1.0089(2) 0.4857(5) 0.25623(10) 0.0436(8) Uani d . 1 1 . .
H H15 0.9577 0.3574 0.2507 0.052 Uiso calc R 1 1 . .
C C16 0.6144(2) 0.6174(5) 0.14430(10) 0.0378(7) Uani d . 1 1 . .
C C17 0.5196(3) 0.5843(6) 0.10811(11) 0.0507(9) Uani d . 1 1 . .
H H17 0.4728 0.4490 0.1084 0.061 Uiso calc R 1 1 . .
C C18 0.4949(3) 0.7500(7) 0.07200(11) 0.0577(9) Uani d . 1 1 . .
H H18 0.4307 0.7263 0.0483 0.069 Uiso calc R 1 1 . .
C C19 0.5635(3) 0.9510(6) 0.07023(11) 0.0559(9) Uani d . 1 1 . .
H H19 0.5454 1.0636 0.0460 0.067 Uiso calc R 1 1 . .
C C20 0.6588(3) 0.9817(6) 0.10486(10) 0.0465(8) Uani d . 1 1 . .
H H20 0.7062 1.1157 0.1035 0.056 Uiso calc R 1 1 . .
C C21 0.6864(2) 0.8180(5) 0.14189(9) 0.0338(7) Uani d . 1 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'
N N 0.0061 0.0033 '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'
O O 0.0106 0.0060 '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
C21 S1 C9 . . 102.73(12) ?
C16 N1 H1A . . 119(2) ?
C16 N1 H1B . . 116.2(19) ?
H1A N1 H1B . . 115(3) ?
C6 C1 C2 . . 119.8(3) ?
C6 C1 H1 . . 120.1 ?
C2 C1 H1 . . 120.1 ?
C3 C2 C1 . . 120.6(3) ?
C3 C2 H2 . . 119.7 ?
C1 C2 H2 . . 119.7 ?
C4 C3 C2 . . 119.8(3) ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
C3 C4 C5 . . 120.5(3) ?
C3 C4 H4 . . 119.7 ?
C5 C4 H4 . . 119.7 ?
C4 C5 C6 . . 120.3(3) ?
C4 C5 H5 . . 119.9 ?
C6 C5 H5 . . 119.9 ?
C1 C6 C5 . . 118.9(3) ?
C1 C6 C7 . . 123.0(3) ?
C5 C6 C7 . . 118.0(3) ?
O1 C7 C6 . . 119.7(3) ?
O1 C7 C8 . . 121.4(3) ?
C6 C7 C8 . . 118.9(3) ?
C7 C8 C9 . . 112.7(2) ?
C7 C8 H8A . . 109.1 ?
C9 C8 H8A . . 109.1 ?
C7 C8 H8B . . 109.1 ?
C9 C8 H8B . . 109.1 ?
H8A C8 H8B . . 107.8 ?
C10 C9 C8 . . 115.0(2) ?
C10 C9 S1 . . 104.94(17) ?
C8 C9 S1 . . 111.25(19) ?
C10 C9 H9 . . 108.5 ?
C8 C9 H9 . . 108.5 ?
S1 C9 H9 . . 108.5 ?
C11 C10 C15 . . 118.2(3) ?
C11 C10 C9 . . 121.9(2) ?
C15 C10 C9 . . 119.8(3) ?
C12 C11 C10 . . 121.0(3) ?
C12 C11 H11 . . 119.5 ?
C10 C11 H11 . . 119.5 ?
C13 C12 C11 . . 120.1(3) ?
C13 C12 H12 . . 120.0 ?
C11 C12 H12 . . 120.0 ?
C12 C13 C14 . . 119.5(3) ?
C12 C13 H13 . . 120.2 ?
C14 C13 H13 . . 120.2 ?
C15 C14 C13 . . 120.4(3) ?
C15 C14 H14 . . 119.8 ?
C13 C14 H14 . . 119.8 ?
C14 C15 C10 . . 120.8(3) ?
C14 C15 H15 . . 119.6 ?
C10 C15 H15 . . 119.6 ?
N1 C16 C17 . . 120.2(3) ?
N1 C16 C21 . . 121.1(3) ?
C17 C16 C21 . . 118.7(3) ?
C18 C17 C16 . . 120.5(3) ?
C18 C17 H17 . . 119.8 ?
C16 C17 H17 . . 119.8 ?
C17 C18 C19 . . 121.1(3) ?
C17 C18 H18 . . 119.4 ?
C19 C18 H18 . . 119.4 ?
C20 C19 C18 . . 118.8(3) ?
C20 C19 H19 . . 120.6 ?
C18 C19 H19 . . 120.6 ?
C19 C20 C21 . . 121.7(3) ?
C19 C20 H20 . . 119.1 ?
C21 C20 H20 . . 119.1 ?
C20 C21 C16 . . 119.3(3) ?
C20 C21 S1 . . 119.3(2) ?
C16 C21 S1 . . 121.2(2) ?
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
S1 C21 . 1.767(3) ?
S1 C9 . 1.843(3) ?
O1 C7 . 1.209(3) ?
N1 C16 . 1.374(4) ?
N1 H1A . 0.89(3) ?
N1 H1B . 0.91(3) ?
C1 C6 . 1.380(4) ?
C1 C2 . 1.384(4) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.370(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.360(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.377(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.387(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.505(4) ?
C7 C8 . 1.515(4) ?
C8 C9 . 1.522(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.512(3) ?
C9 H9 . 0.9800 ?
C10 C11 . 1.382(3) ?
C10 C15 . 1.388(4) ?
C11 C12 . 1.379(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.374(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.377(4) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.371(4) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
C16 C17 . 1.393(4) ?
C16 C21 . 1.400(4) ?
C17 C18 . 1.373(4) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.378(4) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.369(4) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.387(4) ?
C20 H20 . 0.9300 ?
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
N1 H1B Cg1 2_645 0.91(3) 2.55(3) 3.400(3) 155(2)
C12 H12 Cg1 2_755 0.93 2.86 3.581(4) 135
C14 H14 Cg2 2_645 0.93 2.93 3.587(3) 128
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 272500
