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_4034560
_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         'C25 H16 N2 S'
_chemical_formula_sum            'C25 H16 N2 S'
_chemical_formula_weight         376.45
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_audit_creation_date             2018-08-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.932(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.1121(3)
_cell_length_b                   14.1893(3)
_cell_length_c                   21.9733(6)
_cell_measurement_reflns_used    14834
_cell_measurement_temperature    293.9(3)
_cell_measurement_theta_max      28.6740
_cell_measurement_theta_min      2.8520
_cell_volume                     3648.86(16)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.9(3)
_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    -20.00  25.00   1.00    7.50    --  -17.15 -99.00-120.00   45
  2  \w    -25.00  92.00   1.00    7.50    --   18.79  19.00 -30.00  117
  3  \w     -7.00  91.00   1.00    7.50    --   18.79  38.00  30.00   98
  4  \w    -94.00 -34.00   1.00    7.50    --  -17.15 178.00  90.00   60
  5  \w     -3.00  88.00   1.00    7.50    --   18.79  57.00 120.00   91
  6  \w     34.00  81.00   1.00    7.50    --   18.79-178.00 150.00   47
  7  \w    -20.00  61.00   1.00    7.50    --   18.79 -99.00 -30.00   81
;
_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      0.0242280000
_diffrn_orient_matrix_UB_12      0.0094004000
_diffrn_orient_matrix_UB_13      -0.0255303000
_diffrn_orient_matrix_UB_21      0.0531574000
_diffrn_orient_matrix_UB_22      0.0103594000
_diffrn_orient_matrix_UB_23      0.0215435000
_diffrn_orient_matrix_UB_31      0.0162086000
_diffrn_orient_matrix_UB_32      -0.0479723000
_diffrn_orient_matrix_UB_33      -0.0003397000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            38167
_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         26.373
_diffrn_reflns_theta_min         2.621
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77752
_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            yellow
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         7453
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0455P)^2^+1.3079P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1106
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5900
_reflns_number_total             7453
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {cd78dc5c-7180-4152-bc9e-9523f384d437}
_cod_data_source_file            jo9b01793_si_002.cif
_cod_data_source_block           10c
_cod_depositor_comments
;

2020-04-07
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        3648.89(16)
_cod_original_formula_moiety     '2(C25 H16 N2 S)'
_cod_original_formula_sum        'C50 H32 N4 S2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     752.91
_cod_database_code               4034560
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_usercomment     'MD0192 #2'
_shelx_estimated_absorpt_t_max   0.954
_shelx_estimated_absorpt_t_min   0.911
_reflns_odcompleteness_completeness 99.86
_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), C53(H53A,H53B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C20(H20),
 C21(H21), C22(H22), C23(H23), C32(H32), C33(H33), C34(H34), C35(H35), C40(H40),
  C41(H41), C42(H42), C48(H48), C49(H49), C50(H50), C51(H51)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C54(H54A,H54B,H54C)
;
_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 1.491
_oxdiff_exptl_absorpt_empirical_full_min 0.762