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_4034562
_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 H18 N2 O S'
_chemical_formula_sum            'C25 H18 N2 O S'
_chemical_formula_weight         394.47
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-08-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.6911(13)
_cell_length_b                   20.5795(9)
_cell_length_c                   8.1911(4)
_cell_measurement_reflns_used    5036
_cell_measurement_temperature    293.9(4)
_cell_measurement_theta_max      24.4540
_cell_measurement_theta_min      2.8140
_cell_volume                     3825.0(3)
_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_environment      air
_diffrn_ambient_temperature      293.9(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9631
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_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   60.00    --  -17.15 -99.00-120.00   45
  2  \w    -90.00  56.00   1.00   60.00    --  -17.15   0.00 120.00  146
  3  \w    -54.00  44.00   1.00   60.00    --   18.79 -38.00-150.00   98
;
_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      0.0291389000
_diffrn_orient_matrix_UB_12      0.0217745000
_diffrn_orient_matrix_UB_13      -0.0088963000
_diffrn_orient_matrix_UB_21      -0.0110904000
_diffrn_orient_matrix_UB_22      0.0662292000
_diffrn_orient_matrix_UB_23      -0.0185394000
_diffrn_orient_matrix_UB_31      0.0019535000
_diffrn_orient_matrix_UB_32      0.0513897000
_diffrn_orient_matrix_UB_33      0.0276790000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            21414
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.364
_diffrn_reflns_theta_min         2.672
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51806
_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_colour_primary    yellow
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       needle
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1517 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_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     525
_refine_ls_number_reflns         7467
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0981
_refine_ls_R_factor_gt           0.0603
_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^)+(0.0601P)^2^+0.8948P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1343
_refine_ls_wR_factor_ref         0.1553
_reflns_Friedel_coverage         0.781
_reflns_Friedel_fraction_full    0.914
_reflns_Friedel_fraction_max     0.904
_reflns_number_gt                4947
_reflns_number_total             7467
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {646e7e9c-f8b6-416b-8b6e-f12bee972c65}
_cod_data_source_file            jo9b01793_si_002.cif
_cod_data_source_block           10e
_cod_database_code               4034562
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C25 H18 N2 O1 S1'
_chemical_oxdiff_usercomment     'MD0178 #17 klein'
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.912
_reflns_odcompleteness_completeness 99.84
_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, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N29(H29A,H29B), N58(H58A,H58B)
2.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C54(H54A,H54B)
2.c 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), C33(H33), C34(H34), C35(H35), C36(H36), C41(H41),
  C42(H42), C43(H43), C49(H49), C50(H50), C51(H51), C52(H52)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C55(H55A,H55B,H55C)
;
_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 2.001
_oxdiff_exptl_absorpt_empirical_full_min 0.673