Polycyclic Aromatic N-Ethoxycarbonyl Thioamide S-Oxides and Their Triflic Acid Promoted Cyclization to Fluorescent Thiophene Imine-Fused Arenes.
Witalewska, Marzena; Wrona-Piotrowicz, Anna; Makal, Anna; Zakrzewski, Janusz; The Journal of organic chemistry 83 (2018) 1933–1939; doi:10.1021/acs.joc.7b02867

data_4033491
_publ_section_title
;
 Polycyclic Aromatic N-Ethoxycarbonyl Thioamide S-Oxides and Their Triflic
 Acid Promoted Cyclization to Fluorescent Thiophene Imine-Fused Arenes.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1933
_journal_page_last               1939
_journal_paper_doi               10.1021/acs.joc.7b02867
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C24 H17 N O3 S'
_chemical_formula_sum            'C24 H17 N O3 S'
_chemical_formula_weight         399.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-04
_audit_creation_method
;
Olex2 1.2
(compiled Mar  2 2017 14:00:58 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.975(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   28.823(3)
_cell_length_b                   6.1859(6)
_cell_length_c                   10.1655(10)
_cell_measurement_reflns_used    1182
_cell_measurement_temperature    198(130)
_cell_measurement_theta_max      75.0600
_cell_measurement_theta_min      3.1060
_cell_volume                     1790.3(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      198(130)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4391
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_details
'List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames -------------------------------------------------------------------------- 1 \w 28.00 161.00 1.00 60.00 -- 77.29 50.00-150.00 133 2 \w 118.00 163.00 1.00 60.00 -- 77.29 111.00-120.00 45 3 \w 146.00 174.00 1.00 60.00 -- 77.29 111.00 -90.00 28 4 \w 126.00 162.00 1.00 90.00 -- 127.00 104.00 -90.00 36 5 \w 116.00 175.00 1.00 90.00 -- 127.00 77.00 0.00 59 6 \w 126.00 164.00 1.00 60.00 -- 77.29 111.00 30.00 38 7 \w 114.00 160.00 1.00 90.00 -- 127.00 85.00 21.00 46 8 \w 117.00 172.00 1.00 90.00 -- 127.00 104.00 60.00 55 9 \w 120.00 153.00 1.00 90.00 -- 127.00 104.00 120.00 33 10 \w 104.00 178.00 1.00 90.00 -- 127.00 77.00 90.00 74 11 \w 100.00 139.00 1.00 60.00 -- 77.29 111.00 0.00 39 12 \w 103.00 130.00 1.00 60.00 -- 77.29 111.00 -90.00 27 13 \w 78.00 141.00 1.00 60.00 -- 77.29 178.00-180.00 63 14 \w 106.00 133.00 1.00 90.00 -- 127.00 104.00-120.00 27 15 \w 101.00 161.00 1.00 90.00 -- 127.00 104.00 -30.00 60 16 \w 77.00 151.00 1.00 90.00 -- 127.00 77.00 -30.00 74 17 \w 76.00 109.00 1.00 90.00 -- 127.00 77.00 0.00 33 18 \w 58.00 136.00 1.00 60.00 -- 77.29 178.00 120.00 78 19 \w 28.00 80.00 1.00 90.00 -- 127.00 -77.00 -90.00 52 20 \w -62.00 -35.00 1.00 30.00 -- 27.59-178.00-120.00 27 21 \w -129.00 -84.00 1.00 30.00 -- -27.59 -99.00-120.00 45 22 \w -130.00 20.00 1.00 30.00 -- -27.59 -37.00 150.00 150 23 \w -75.00 -44.00 1.00 30.00 -- 27.59 178.00 90.00 31'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0314258682
_diffrn_orient_matrix_UB_12      0.1722542159
_diffrn_orient_matrix_UB_13      0.0512600940
_diffrn_orient_matrix_UB_21      -0.0437277449
_diffrn_orient_matrix_UB_22      -0.1375471621
_diffrn_orient_matrix_UB_23      -0.0502543312
_diffrn_orient_matrix_UB_31      0.0051554298
_diffrn_orient_matrix_UB_32      -0.1160079614
_diffrn_orient_matrix_UB_33      0.1355855085
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_Laue_measured_fraction_full 0.927
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6196
_diffrn_reflns_point_group_measured_fraction_full 0.927
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.237
_diffrn_reflns_theta_min         3.104
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.837
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3413
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1061
_refine_ls_R_factor_gt           0.0748
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.1325P)^2^+0.6828P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2011
_refine_ls_wR_factor_ref         0.2250
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2309
_reflns_number_total             3413
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02867_si_005.cif
_cod_data_source_block           mwit00159
_cod_depositor_comments
'Adding full bibliography for 4033490--4033495.cif.'
_cod_database_code               4033491
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C24 H20 N O3 S'
_chemical_oxdiff_usercomment     '100 K, colourless prism'
_reflns_odcompleteness_completeness 90.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1
 0.86 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12),
 C15(H15), C16(H16), C17(H17)
3.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_olex2_date_sample_data_collection 2017-03-02
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
'Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling'
_oxdiff_exptl_absorpt_empirical_full_max 1.790
_oxdiff_exptl_absorpt_empirical_full_min 0.680