Bay-Substituted Thiaza[5]helicenes: Synthesis and Implications on Structural and Spectroscopic Properties.
Daniels, Mathias; de Jong, Flip; Vandermeeren, Tom; Van Meervelt, Luc; Van der Auweraer, Mark; Dehaen, Wim; The Journal of organic chemistry 84 (2019) 13528–13539; doi:10.1021/acs.joc.9b01793

data_4034558
_publ_section_title
;
 Bay-Substituted Thiaza[5]helicenes: Synthesis and Implications on
 Structural and Spectroscopic Properties.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13528
_journal_page_last               13539
_journal_paper_doi               10.1021/acs.joc.9b01793
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C24 H17 N S'
_chemical_formula_sum            'C24 H17 N S'
_chemical_formula_weight         351.44
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-11-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-12 # Formatted by publCIF

;
_cell_angle_alpha                73.9262(19)
_cell_angle_beta                 79.3366(16)
_cell_angle_gamma                79.3046(16)
_cell_formula_units_Z            4
_cell_length_a                   11.04919(18)
_cell_length_b                   12.5553(3)
_cell_length_c                   13.5552(3)
_cell_measurement_reflns_used    26703
_cell_measurement_temperature    294.1(2)
_cell_measurement_theta_max      27.7910
_cell_measurement_theta_min      3.0490
_cell_volume                     1757.67(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      294.1(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9631
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -86.00   4.00   1.00    5.00    --  -17.15 -57.00-180.00   90
  2  \w    -87.00  13.00   1.00    5.00    --  -17.15 -77.00  90.00  100
  3  \w    -39.00  52.00   1.00    5.00    --  -17.15  57.00  30.00   91
  4  \w    -39.00  52.00   1.00    5.00    --  -17.15  57.00-150.00   91
  5  \w    -86.00   4.00   1.00    5.00    --  -17.15 -57.00 -60.00   90
  6  \w    -61.00  56.00   1.00    5.00    --  -17.15  19.00   0.00  117
  7  \w    -39.00  52.00   1.00    5.00    --  -17.15  57.00  90.00   91
  8  \w    -86.00   4.00   1.00    5.00    --  -17.15 -57.00  30.00   90
  9  \w      4.00  78.00   1.00    5.00    --   18.79-128.00 -27.79   74
 10  \w      8.00  82.00   1.00    5.00    --   18.79-134.00 146.27   74
 11  \w    -20.00  25.00   1.00    5.00    --  -17.15 -99.00-150.00   45
 12  \w    -93.00 -35.00   1.00    5.00    --  -17.15-178.00  30.00   58
 13  \w    -20.00  61.00   1.00    5.00    --   18.79 -99.00-150.00   81
 14  \w    -54.00  92.00   1.00    5.00    --   18.79   0.00-180.00  146
 15  \w    -54.00  92.00   1.00    5.00    --   18.79   0.00-150.00  146
 16  \w    -54.00  92.00   1.00    5.00    --   18.79   0.00-120.00  146
 17  \w    -54.00  92.00   1.00    5.00    --   18.79   0.00 -90.00  146
 18  \w    -25.00  92.00   1.00    5.00    --   18.79  19.00 -60.00  117
 19  \w    -54.00  62.00   1.00    5.00    --   18.79   0.00 -30.00  116
 20  \w    -54.00  92.00   1.00    5.00    --   18.79   0.00 -60.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0015018000
_diffrn_orient_matrix_UB_12      -0.0487053000
_diffrn_orient_matrix_UB_13      0.0417997000
_diffrn_orient_matrix_UB_21      -0.0211132000
_diffrn_orient_matrix_UB_22      -0.0290979000
_diffrn_orient_matrix_UB_23      -0.0300561000
_diffrn_orient_matrix_UB_31      0.0625076000
_diffrn_orient_matrix_UB_32      -0.0175804000
_diffrn_orient_matrix_UB_33      -0.0193774000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            72352
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.424
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90481
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         7170
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0501
_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^)+(0.0568P)^2^+0.9082P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1324
_refine_ls_wR_factor_ref         0.1421
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5766
_reflns_number_total             7170
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01793_si_002.cif
_cod_data_source_block           10a
_cod_original_cell_volume        1757.67(6)
_cod_database_code               4034558
_publcif_datablock.id            {a622269d-9768-4e50-9f93-cf3850955e42}
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C24 H17 N1 S1'
_chemical_oxdiff_usercomment     MD0209
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C25(H25A,H25B), C51(H51A,H51B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15),
 C20(H20), C21(H21), C22(H22), C23(H23), C30(H30), C31(H31), C32(H32), C33(H33),
  C38(H38), C39(H39), C40(H40), C41(H41), C46(H46), C47(H47), C48(H48), C49(H49)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C52(H52A,H52B,H52C)
;
_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 1.187
_oxdiff_exptl_absorpt_empirical_full_min 0.883