#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/58/2015895.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_2015895
loop_
_publ_author_name
'Betül Şen'
'Gülsiye Öztürk'
'Serap Alp'
'Aygün, Muhittin'
'Büyükgüngör, Orhan'
_publ_section_title
;
 2-Methoxy-4-[(5-oxo-2-phenyl-4,5-dihydro-1,3-oxazol-4-ylidene)methyl]phenyl
 4-methylbenzenesulfonate
;
_journal_coeditor_code           GD3084
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o223
_journal_page_last               o224
_journal_paper_doi               10.1107/S0108270107005720
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C24 H19 N O6 S'
_chemical_formula_moiety         'C24 H19 N O6 S'
_chemical_formula_sum            'C24 H19 N O6 S'
_chemical_formula_weight         449.46
_chemical_name_systematic
;
2-Methoxy-4-[(5-oxo-2-phenyl-4,5-dihydrooxazol-4-ylidene)methyl]phenyl
4-methylphenylsulfonate
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.338(8)
_cell_angle_beta                 94.775(8)
_cell_angle_gamma                99.492(8)
_cell_formula_units_Z            2
_cell_length_a                   6.7854(7)
_cell_length_b                   10.2766(11)
_cell_length_c                   16.0242(15)
_cell_measurement_reflns_used    10980
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      2.1
_cell_volume                     1072.82(19)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics
'ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2003)'
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       'rotation method'
_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  0.0674
_diffrn_reflns_av_sigmaI/netI    0.0663
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9923
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.06
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.9900
_exptl_absorpt_correction_T_min  0.9131
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.297
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4206
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0503
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0655P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1325
_reflns_number_gt                2745
_reflns_number_total             4206
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd3084.cif
_cod_data_source_block           I
_cod_database_code               2015895
_cod_database_fobs_code          2015895
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
S S1 1.29957(10) 0.66402(7) 0.32696(4) 0.0530(2) Uani d . 1
O O1 1.1203(3) 0.7162(2) 0.31612(14) 0.0707(6) Uani d . 1
O O2 1.4398(3) 0.7151(2) 0.40157(11) 0.0712(6) Uani d . 1
O O3 1.2439(2) 0.50631(19) 0.32655(10) 0.0510(4) Uani d . 1
O O4 0.9025(2) 0.4826(2) 0.39867(10) 0.0568(5) Uani d . 1
O O5 0.0760(3) -0.0186(2) 0.17185(11) 0.0604(5) Uani d . 1
O O6 0.2011(3) -0.0574(3) 0.04480(12) 0.0784(7) Uani d . 1
N N1 0.3301(3) 0.1362(2) 0.25366(12) 0.0530(5) Uani d . 1
C C1 1.3347(4) 0.6999(3) 0.16492(18) 0.0651(8) Uani d . 1
H H1 1.2066 0.7209 0.1646 0.078 Uiso calc R 1
C C2 1.4368(5) 0.7012(4) 0.09410(19) 0.0760(9) Uani d . 1
H H2 1.3762 0.7239 0.0461 0.091 Uiso calc R 1
C C3 1.6271(4) 0.6696(3) 0.09266(17) 0.0645(8) Uani d . 1
C C4 1.7129(4) 0.6370(4) 0.16481(18) 0.0687(8) Uani d . 1
H H4 1.8402 0.6145 0.1650 0.082 Uiso calc R 1
C C5 1.6156(4) 0.6368(3) 0.23640(17) 0.0619(7) Uani d . 1
H H5 1.6777 0.6165 0.2850 0.074 Uiso calc R 1
C C6 1.4252(4) 0.6670(3) 0.23591(15) 0.0479(6) Uani d . 1
C C7 1.7383(6) 0.6747(5) 0.0155(2) 0.0956(12) Uani d . 1
H H7A 1.6455 0.6407 -0.0358 0.143 Uiso calc R 1
H H7B 1.8404 0.6203 0.0160 0.143 Uiso calc R 1
H H7C 1.7998 0.7664 0.0170 0.143 Uiso calc R 1
C C8 1.0672(4) 0.4275(3) 0.27784(14) 0.0462(6) Uani d . 1
C C9 1.0740(4) 0.3604(3) 0.19517(15) 0.0530(6) Uani d . 1
H H9 1.1914 0.3746 0.1695 0.064 Uiso calc R 1
C C10 0.9064(4) 0.2724(3) 0.15071(15) 0.0556(7) Uani d . 1
H H10 0.9103 0.2278 0.0946 0.067 Uiso calc R 1
C C11 0.7307(4) 0.2496(3) 0.18934(14) 0.0501(6) Uani d . 1
C C12 0.7265(4) 0.3201(3) 0.27343(14) 0.0491(6) Uani d . 1
H H12 0.6095 0.3060 0.2994 0.059 Uiso calc R 1
C C13 0.8925(3) 0.4095(3) 0.31802(13) 0.0460(6) Uani d . 1
C C14 0.7296(4) 0.4603(3) 0.44316(15) 0.0595(7) Uani d . 1
H H14A 0.7555 0.5176 0.4994 0.089 Uiso calc R 1
H H14B 0.7018 0.3675 0.4479 0.089 Uiso calc R 1
H H14C 0.6157 0.4807 0.4120 0.089 Uiso calc R 1
C C15 0.5599(4) 0.1491(3) 0.14287(15) 0.0551(7) Uani d . 1
H H15 0.5716 0.1131 0.0859 0.066 Uiso calc R 1
C C16 0.3884(4) 0.1021(3) 0.17160(15) 0.0529(6) Uani d . 1
C C17 0.2233(4) 0.0023(3) 0.11840(16) 0.0576(7) Uani d . 1
C C18 0.1535(4) 0.0662(3) 0.25011(16) 0.0527(6) Uani d . 1
C C19 0.0275(4) 0.0699(3) 0.31908(17) 0.0572(7) Uani d . 1
C C20 -0.1704(5) 0.0005(3) 0.3049(2) 0.0704(8) Uani d . 1
H H20 -0.2228 -0.0530 0.2513 0.085 Uiso calc R 1
C C21 -0.2878(6) 0.0117(4) 0.3710(3) 0.0874(11) Uani d . 1
H H21 -0.4204 -0.0343 0.3618 0.105 Uiso calc R 1
C C22 -0.2112(6) 0.0901(4) 0.4504(3) 0.0902(11) Uani d . 1
H H22 -0.2921 0.0966 0.4946 0.108 Uiso calc R 1
C C23 -0.0155(6) 0.1591(4) 0.4650(2) 0.0877(11) Uani d . 1
H H23 0.0358 0.2123 0.5188 0.105 Uiso calc R 1
C C24 0.1038(5) 0.1491(4) 0.39950(18) 0.0723(8) Uani d . 1
H H24 0.2362 0.1956 0.4092 0.087 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'
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
_geom_angle_publ_flag
O1 S1 O2 120.99(14) y
O1 S1 O3 109.56(12) y
O2 S1 O3 103.03(12) y
O1 S1 C6 109.18(13) y
O2 S1 C6 109.30(12) y
O3 S1 C6 103.23(11) y
C8 O3 S1 119.98(16) y
C13 O4 C14 117.48(19) ?
C17 O5 C18 105.00(19) ?
C18 N1 C16 105.8(2) ?
C2 C1 C6 119.0(3) ?
C2 C1 H1 120.5 ?
C6 C1 H1 120.5 ?
C1 C2 C3 121.7(3) ?
C1 C2 H2 119.2 ?
C3 C2 H2 119.2 ?
C2 C3 C4 117.7(2) ?
C2 C3 C7 120.9(3) ?
C4 C3 C7 121.3(3) ?
C5 C4 C3 121.7(3) ?
C5 C4 H4 119.2 ?
C3 C4 H4 119.2 ?
C4 C5 C6 119.5(3) ?
C4 C5 H5 120.2 ?
C6 C5 H5 120.2 ?
C1 C6 C5 120.4(2) ?
C1 C6 S1 120.2(2) ?
C5 C6 S1 119.4(2) ?
C3 C7 H7A 109.5 ?
C3 C7 H7B 109.5 ?
H7A C7 H7B 109.5 ?
C3 C7 H7C 109.5 ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
C9 C8 C13 121.6(2) ?
C9 C8 O3 119.8(2) ?
C13 C8 O3 118.4(2) ?
C8 C9 C10 119.7(2) ?
C8 C9 H9 120.1 ?
C10 C9 H9 120.1 ?
C9 C10 C11 120.3(2) ?
C9 C10 H10 119.8 ?
C11 C10 H10 119.8 ?
C10 C11 C12 119.0(2) ?
C10 C11 C15 119.2(2) ?
C12 C11 C15 121.8(2) ?
C13 C12 C11 121.1(2) ?
C13 C12 H12 119.5 ?
C11 C12 H12 119.5 ?
O4 C13 C12 125.4(2) ?
O4 C13 C8 116.3(2) ?
C12 C13 C8 118.3(2) ?
O4 C14 H14A 109.5 ?
O4 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
O4 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
C11 C15 C16 128.3(2) y
C16 C15 H15 115.8 ?
C11 C15 H15 115.8 ?
C15 C16 N1 128.6(2) ?
C15 C16 C17 123.8(2) ?
N1 C16 C17 107.6(2) ?
O6 C17 O5 121.4(3) ?
O6 C17 C16 133.0(3) ?
O5 C17 C16 105.6(2) ?
N1 C18 O5 116.0(2) ?
N1 C18 C19 126.3(2) ?
O5 C18 C19 117.6(2) ?
C24 C19 C20 119.7(3) ?
C24 C19 C18 119.2(3) ?
C20 C19 C18 121.1(3) ?
C19 C20 C21 119.2(3) ?
C19 C20 H20 120.4 ?
C21 C20 H20 120.4 ?
C22 C21 C20 120.7(3) ?
C22 C21 H21 119.6 ?
C20 C21 H21 119.6 ?
C23 C22 C21 120.4(3) ?
C23 C22 H22 119.8 ?
C21 C22 H22 119.8 ?
C22 C23 C24 119.7(3) ?
C22 C23 H23 120.2 ?
C24 C23 H23 120.2 ?
C23 C24 C19 120.3(3) ?
C23 C24 H24 119.9 ?
C19 C24 H24 119.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O1 1.419(2) ?
S1 O2 1.418(2) ?
S1 O3 1.601(2) ?
S1 C6 1.753(2) ?
O3 C8 1.407(3) ?
O4 C13 1.351(3) ?
O4 C14 1.432(3) ?
O5 C17 1.387(3) y
O5 C18 1.385(3) y
O6 C17 1.202(3) y
N1 C16 1.400(3) y
N1 C18 1.283(3) y
C1 C2 1.379(4) ?
C1 C6 1.374(4) ?
C1 H1 0.9300 ?
C2 C3 1.383(4) ?
C2 H2 0.9300 ?
C3 C4 1.376(4) ?
C3 C7 1.507(4) ?
C4 C5 1.371(4) ?
C4 H4 0.9300 ?
C5 C6 1.377(4) ?
C5 H5 0.9300 ?
C7 H7A 0.9600 ?
C7 H7B 0.9600 ?
C7 H7C 0.9600 ?
C8 C9 1.376(3) ?
C8 C13 1.398(3) ?
C9 C10 1.375(4) ?
C9 H9 0.9300 ?
C10 C11 1.395(4) ?
C10 H10 0.9300 ?
C11 C12 1.404(3) ?
C11 C15 1.457(4) y
C12 C13 1.375(3) ?
C12 H12 0.9300 ?
C14 H14A 0.9600 ?
C14 H14B 0.9600 ?
C14 H14C 0.9600 ?
C15 C16 1.339(4) y
C15 H15 0.9300 ?
C16 C17 1.467(4) y
C18 C19 1.451(4) ?
C19 C24 1.389(4) ?
C19 C20 1.390(4) ?
C20 C21 1.376(5) ?
C20 H20 0.9300 ?
C21 C22 1.374(5) ?
C21 H21 0.9300 ?
C22 C23 1.376(5) ?
C22 H22 0.9300 ?
C23 C24 1.376(5) ?
C23 H23 0.9300 ?
C24 H24 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
C10 H10 O6 2_655 0.93 2.52 3.405(3) 158
C12 H12 N1 . 0.93 2.31 2.975(4) 128
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
_geom_torsion_publ_flag
O1 S1 O3 C8 31.07(19) ?
O2 S1 O3 C8 161.09(16) ?
C6 S1 O3 C8 -85.14(18) y
C6 C1 C2 C3 0.3(5) ?
C1 C2 C3 C4 -0.3(5) ?
C1 C2 C3 C7 -178.6(4) ?
C2 C3 C4 C5 -0.7(5) ?
C7 C3 C4 C5 177.7(3) ?
C3 C4 C5 C6 1.5(5) ?
C2 C1 C6 C5 0.5(5) ?
C2 C1 C6 S1 -179.9(3) ?
C4 C5 C6 C1 -1.4(5) ?
C4 C5 C6 S1 179.0(3) ?
O1 S1 C6 C1 -7.7(3) ?
O2 S1 C6 C1 -142.1(2) ?
O3 S1 C6 C1 108.8(2) ?
O1 S1 C6 C5 171.9(2) ?
O2 S1 C6 C5 37.5(3) ?
O3 S1 C6 C5 -71.6(2) ?
S1 O3 C8 C9 92.3(3) ?
S1 O3 C8 C13 -93.6(3) ?
C13 C8 C9 C10 -0.7(4) ?
O3 C8 C9 C10 173.2(2) ?
C8 C9 C10 C11 -0.7(4) ?
C9 C10 C11 C12 1.4(4) ?
C9 C10 C11 C15 -175.9(3) ?
C10 C11 C12 C13 -0.6(4) ?
C15 C11 C12 C13 176.6(3) ?
C14 O4 C13 C12 3.4(4) ?
C14 O4 C13 C8 -176.4(2) ?
C11 C12 C13 O4 179.4(3) ?
C11 C12 C13 C8 -0.7(4) ?
C9 C8 C13 O4 -178.8(2) ?
O3 C8 C13 O4 7.3(4) ?
C9 C8 C13 C12 1.4(4) ?
O3 C8 C13 C12 -172.6(2) ?
C10 C11 C15 C16 172.0(3) ?
C12 C11 C15 C16 -5.2(5) ?
C11 C15 C16 N1 -0.7(5) ?
C11 C15 C16 C17 178.6(3) ?
C18 N1 C16 C15 179.4(3) ?
C18 N1 C16 C17 0.0(3) ?
C18 O5 C17 O6 -179.9(3) ?
C18 O5 C17 C16 0.7(3) ?
C15 C16 C17 O6 0.9(6) ?
N1 C16 C17 O6 -179.7(3) ?
C15 C16 C17 O5 -180.0(3) ?
N1 C16 C17 O5 -0.5(3) ?
C16 N1 C18 O5 0.6(3) ?
C16 N1 C18 C19 -178.0(3) ?
C17 O5 C18 N1 -0.9(3) ?
C17 O5 C18 C19 177.8(3) ?
N1 C18 C19 C24 -4.4(5) ?
O5 C18 C19 C24 177.1(3) ?
N1 C18 C19 C20 172.7(3) ?
O5 C18 C19 C20 -5.8(4) ?
C24 C19 C20 C21 0.2(5) ?
C18 C19 C20 C21 -177.0(3) ?
C19 C20 C21 C22 -0.2(6) ?
C20 C21 C22 C23 0.2(6) ?
C21 C22 C23 C24 -0.1(6) ?
C22 C23 C24 C19 0.0(6) ?
C20 C19 C24 C23 -0.1(5) ?
C18 C19 C24 C23 177.1(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1418112
