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_4033494
_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         'C28 H31 N O3 S'
_chemical_formula_sum            'C28 H31 N O3 S'
_chemical_formula_weight         461.60
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-02-22
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                88.443(2)
_cell_angle_beta                 80.206(2)
_cell_angle_gamma                70.222(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6888(2)
_cell_length_b                   8.7220(2)
_cell_length_c                   16.7794(4)
_cell_measurement_reflns_used    27099
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      33.8810
_cell_measurement_theta_min      2.4330
_cell_volume                     1178.52(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_details
;
  1 omega  -11.00  126.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       32.1364   57.0000 -150.0000 137

  2 omega  -60.00   71.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       32.1364  -37.0000  -30.0000 131

  3 omega  -12.00  135.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       32.1364   77.0000  -90.0000 147

  4 omega  -11.00  126.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       32.1364   57.0000   90.0000 137

  5 omega   35.00  135.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       32.1364  178.0000 -180.0000 100

  6 omega  -12.00  135.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       32.1364   77.0000  -30.0000 147

  7 omega -136.00  -57.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.3864 -178.0000 -180.0000 79

  8 omega    2.00   33.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.3864 -125.0000   32.1735 31

  9 omega  -76.00   61.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.3864   57.0000 -120.0000 137

 10 omega  -70.00  134.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       32.1364    0.0000 -120.0000 204

 11 omega  -70.00  134.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       32.1364    0.0000 -150.0000 204

 12 omega  -11.00  126.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       32.1364   57.0000 -180.0000 137

 13 omega  -70.00  134.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       32.1364    0.0000 -180.0000 204

 14 omega    4.00   26.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.3864 -128.0000  -79.1511 22
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0623294000
_diffrn_orient_matrix_UB_12      -0.0758157000
_diffrn_orient_matrix_UB_13      0.0040931000
_diffrn_orient_matrix_UB_21      0.0620315000
_diffrn_orient_matrix_UB_22      0.0327578000
_diffrn_orient_matrix_UB_23      -0.0173369000
_diffrn_orient_matrix_UB_31      0.0044520000
_diffrn_orient_matrix_UB_32      0.0256044000
_diffrn_orient_matrix_UB_33      0.0390492000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            58217
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.134
_diffrn_reflns_theta_min         2.465
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description
;
;
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         9247
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0382
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0502P)^2^+0.4571P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1083
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8173
_reflns_number_total             9247
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02867_si_004.cif
_cod_data_source_block           exp_630
_cod_depositor_comments
'Adding full bibliography for 4033490--4033495.cif.'
_cod_original_cell_volume        1178.51(6)
_cod_database_code               4033494
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.50
_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:
 C19(H19A,H19B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C8(H8), C10(H10), C12(H12), C13(H13)
3.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C)
;
_olex2_date_sample_data_collection 2016-02-16
_olex2_submission_special_instructions 'No special instructions were received'