#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/20/2212066.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_2212066
loop_
_publ_author_name
'Yazıcı, Serap'
'Türköz, Nalan'
'Kütük, Halil '
'Şenel, İsmet '
'Büyükgüngör, Orhan'
_publ_section_title
;
 N-(p-Methoxyphenylsulfanyl)phthalimide
;
_journal_coeditor_code           BT2248
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o813
_journal_page_last               o814
_journal_paper_doi               10.1107/S1600536807002541
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C15 H11 N1 O3 S'
_chemical_formula_moiety         'C15 H11 N1 O3 S'
_chemical_formula_sum            'C15 H11 N O3 S'
_chemical_formula_weight         285.31
_chemical_name_systematic
;
N-(p-Methoxyphenylsulfanyl)phthalimide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                109.586(9)
_cell_angle_beta                 93.093(9)
_cell_angle_gamma                112.998(9)
_cell_formula_units_Z            2
_cell_length_a                   8.2600(9)
_cell_length_b                   8.4479(10)
_cell_length_c                   11.4776(13)
_cell_measurement_reflns_used    13815
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.99
_cell_measurement_theta_min      2.74
_cell_volume                     678.61(16)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       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  0.0588
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10429
_diffrn_reflns_theta_full        27.81
_diffrn_reflns_theta_max         27.81
_diffrn_reflns_theta_min         2.74
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  0.9901
_exptl_absorpt_correction_T_min  0.8950
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.680
_exptl_crystal_size_mid          0.377
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.230
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3185
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0427
_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)+(0.0376P)²+0.1535P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1051
_reflns_number_gt                2443
_reflns_number_total             3185
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2248.cif
_cod_data_source_block           I
_cod_original_cell_volume        678.61(13)
_cod_original_formula_sum        'C15 H11 N1 O3 S'
_cod_database_code               2212066
_cod_database_fobs_code          2212066
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C C1 0.4144(3) -0.1867(3) 0.67768(18) 0.0558(4) Uani d . 1
C C2 0.3187(2) -0.3709(2) 0.57289(17) 0.0506(4) Uani d . 1
C C3 0.3076(3) -0.5418(3) 0.5630(2) 0.0664(5) Uani d . 1
H H3 0.3654 -0.5553 0.6284 0.080 Uiso calc R 1
C C4 0.2068(3) -0.6930(3) 0.4518(2) 0.0720(6) Uani d . 1
H H4 0.1967 -0.8105 0.4423 0.086 Uiso calc R 1
C C5 0.1208(3) -0.6734(3) 0.3545(2) 0.0691(6) Uani d . 1
H H5 0.0538 -0.7776 0.2809 0.083 Uiso calc R 1
C C6 0.1331(3) -0.5008(3) 0.36490(18) 0.0599(5) Uani d . 1
H H6 0.0763 -0.4865 0.2995 0.072 Uiso calc R 1
C C7 0.2322(2) -0.3518(2) 0.47553(16) 0.0473(4) Uani d . 1
C C8 0.2695(2) -0.1538(2) 0.51383(16) 0.0499(4) Uani d . 1
C C9 0.3100(3) 0.1927(2) 0.81749(17) 0.0528(4) Uani d . 1
C C10 0.1468(3) 0.1829(3) 0.77111(17) 0.0554(4) Uani d . 1
H H10 0.1158 0.1608 0.6862 0.066 Uiso calc R 1
C C11 0.0296(3) 0.2055(3) 0.84908(17) 0.0565(4) Uani d . 1
H H11 -0.0808 0.1962 0.8165 0.068 Uiso calc R 1
C C12 0.0768(3) 0.2420(3) 0.97576(17) 0.0610(5) Uani d . 1
C C13 0.2396(3) 0.2512(4) 1.0224(2) 0.0854(8) Uani d . 1
H H13 0.2715 0.2750 1.1076 0.103 Uiso calc R 1
C C14 0.3539(3) 0.2258(4) 0.9442(2) 0.0764(6) Uani d . 1
H H14 0.4623 0.2307 0.9763 0.092 Uiso calc R 1
C C15 -0.1962(3) 0.2593(4) 1.0200(2) 0.0830(7) Uani d . 1
H H15A -0.2527 0.2839 1.0906 0.124 Uiso calc R 1
H H15B -0.2701 0.1362 0.9580 0.124 Uiso calc R 1
H H15C -0.1817 0.3491 0.9829 0.124 Uiso calc R 1
N N1 0.3781(2) -0.0616(2) 0.63636(14) 0.0519(3) Uani d . 1
O O1 0.5043(2) -0.1442(2) 0.77865(15) 0.0841(5) Uani d . 1
O O2 0.2202(2) -0.0804(2) 0.45546(14) 0.0729(4) Uani d . 1
O O3 -0.0244(2) 0.2724(3) 1.06214(13) 0.0872(5) Uani d . 1
S S1 0.46624(7) 0.17248(7) 0.72051(5) 0.06249(16) 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'
N N 0.0061 0.0033 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 N1 124.98(19)
O1 C1 C2 129.63(18)
N1 C1 C2 105.39(15)
C3 C2 C7 121.13(18)
C3 C2 C1 129.92(18)
C7 C2 C1 108.95(15)
C2 C3 C4 117.2(2)
C2 C3 H3 121.4
C4 C3 H3 121.4
C5 C4 C3 121.49(19)
C5 C4 H4 119.3
C3 C4 H4 119.3
C4 C5 C6 120.9(2)
C4 C5 H5 119.5
C6 C5 H5 119.5
C7 C6 C5 117.31(19)
C7 C6 H6 121.3
C5 C6 H6 121.3
C6 C7 C2 121.88(16)
C6 C7 C8 129.68(16)
C2 C7 C8 108.44(15)
O2 C8 N1 125.16(17)
O2 C8 C7 128.90(17)
N1 C8 C7 105.93(14)
C10 C9 C14 118.73(17)
C10 C9 S1 121.70(14)
C14 C9 S1 119.53(15)
C11 C10 C9 120.89(17)
C11 C10 H10 119.6
C9 C10 H10 119.6
C10 C11 C12 119.71(17)
C10 C11 H11 120.1
C12 C11 H11 120.1
O3 C12 C11 125.06(17)
O3 C12 C13 115.36(17)
C11 C12 C13 119.57(18)
C14 C13 C12 120.41(19)
C14 C13 H13 119.8
C12 C13 H13 119.8
C13 C14 C9 120.67(19)
C13 C14 H14 119.7
C9 C14 H14 119.7
O3 C15 H15A 109.5
O3 C15 H15B 109.5
H15A C15 H15B 109.5
O3 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C8 N1 C1 111.28(15)
C8 N1 S1 124.43(12)
C1 N1 S1 124.17(13)
C12 O3 C15 118.39(17)
N1 S1 C9 102.52(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.201(2)
C1 N1 1.414(2)
C1 C2 1.475(3)
C2 C3 1.376(3)
C2 C7 1.382(2)
C3 C4 1.384(3)
C3 H3 0.9300
C4 C5 1.382(3)
C4 H4 0.9300
C5 C6 1.385(3)
C5 H5 0.9300
C6 C7 1.370(3)
C6 H6 0.9300
C7 C8 1.475(2)
C8 O2 1.202(2)
C8 N1 1.405(2)
C9 C10 1.383(3)
C9 C14 1.384(3)
C9 S1 1.7700(19)
C10 C11 1.377(3)
C10 H10 0.9300
C11 C12 1.380(3)
C11 H11 0.9300
C12 O3 1.354(2)
C12 C13 1.383(3)
C13 C14 1.365(3)
C13 H13 0.9300
C14 H14 0.9300
C15 O3 1.424(3)
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
N1 S1 1.7004(15)
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
C4 H4 O2 1_545 0.93 2.42 3.332(3) 168.4
C15 H15B O1 1_455 0.96 2.49 3.428(3) 166
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
O1 C1 C2 C3 -0.3(3)
N1 C1 C2 C3 -179.64(18)
O1 C1 C2 C7 179.7(2)
N1 C1 C2 C7 0.37(19)
C7 C2 C3 C4 0.1(3)
C1 C2 C3 C4 -179.90(18)
C2 C3 C4 C5 0.1(3)
C3 C4 C5 C6 0.2(3)
C4 C5 C6 C7 -0.5(3)
C5 C6 C7 C2 0.6(3)
C5 C6 C7 C8 179.92(17)
C3 C2 C7 C6 -0.5(3)
C1 C2 C7 C6 179.54(16)
C3 C2 C7 C8 -179.87(16)
C1 C2 C7 C8 0.12(19)
C6 C7 C8 O2 0.0(3)
C2 C7 C8 O2 179.34(19)
C6 C7 C8 N1 -179.92(18)
C2 C7 C8 N1 -0.57(19)
C14 C9 C10 C11 0.0(3)
S1 C9 C10 C11 -177.71(14)
C9 C10 C11 C12 1.3(3)
C10 C11 C12 O3 177.89(19)
C10 C11 C12 C13 -1.5(3)
O3 C12 C13 C14 -179.0(2)
C11 C12 C13 C14 0.5(4)
C12 C13 C14 C9 0.8(4)
C10 C9 C14 C13 -1.0(4)
S1 C9 C14 C13 176.7(2)
O2 C8 N1 C1 -179.09(18)
C7 C8 N1 C1 0.82(19)
O2 C8 N1 S1 -2.9(3)
C7 C8 N1 S1 177.05(11)
O1 C1 N1 C8 179.84(19)
C2 C1 N1 C8 -0.7(2)
O1 C1 N1 S1 3.6(3)
C2 C1 N1 S1 -176.99(11)
C11 C12 O3 C15 2.5(3)
C13 C12 O3 C15 -178.1(2)
C8 N1 S1 C9 96.92(15)
C1 N1 S1 C9 -87.33(16)
C10 C9 S1 N1 -78.45(16)
C14 C9 S1 N1 103.88(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21125499
