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_4033492
_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         'C56 H58 N2 O4 S2'
_chemical_formula_sum            'C56 H58 N2 O4 S2'
_chemical_formula_weight         887.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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     dual
_audit_creation_date             2017-03-02
_audit_creation_method
;
Olex2 1.2
(compiled Feb 23 2017 12:29:26 for OlexSys, GUI svn.r5320)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.358(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8231(12)
_cell_length_b                   26.649(3)
_cell_length_c                   18.153(2)
_cell_measurement_reflns_used    9327
_cell_measurement_temperature    100.1(1)
_cell_measurement_theta_max      26.66
_cell_measurement_theta_min      2.17
_cell_volume                     4603.6(9)
_computing_cell_refinement       'APEX2 v2012.4-3 (Bruker AXS)'
_computing_data_collection       'APEX2 v2012.4-3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_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    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.1(1)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker kappa APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.1190
_diffrn_reflns_av_unetI/netI     0.0732
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            84140
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.800
_diffrn_reflns_theta_min         1.387
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9554
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0683 before and 0.0618 after correction. The Ratio of minimum to maximum transmission is 0.9554. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       plate
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     591
_refine_ls_number_reflns         7933
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1400
_refine_ls_R_factor_gt           0.0690
_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^)+(0.0979P)^2^+5.7994P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1732
_refine_ls_wR_factor_ref         0.2124
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4512
_reflns_number_total             7933
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02867_si_010.cif
_cod_data_source_block           mwit00164ab
_cod_depositor_comments
'Adding full bibliography for 4033490--4033495.cif.'
_cod_original_cell_volume        4603.6(10)
_cod_database_code               4033492
_shelxl_version_number           2013-2
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C49(H49A,H49B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C8(H8), C10(H10), C13(H13), C33(H33), C34(H34), C36(H36),
 C38(H38), C40(H40), C41(H41), C43(H43)
2.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), C50(H50A,
 H50B,H50C), C52(H52A,H52B,H52C), C53(H53A,H53B,H53C), C54(H54A,H54B,H54C),
 C56(H56A,H56B,H56C), C57(H57A,H57B,H57C), C58(H58A,H58B,H58C)
;
_olex2_submission_special_instructions 'No special instructions were received'