Convergent Strategy for the Synthesis of Oxa-, Thia-, and Selena[5]helicenes by Acetylene-Activated S<sub>N</sub>Ar Reactions.
Hoenig, Samuel M.; Yan, Youmian; Dougherty, Emily A.; Hudson, Reuben; Petovic, Sava; Lee, Christopher K.; Hu, Yusheng; Gomez, Lucas S.; Katz, Jeffrey L.; The Journal of organic chemistry 85 (2020) 4553–4559; doi:10.1021/acs.joc.0c00052

data_4038057
_publ_section_title
;
 Convergent Strategy for the Synthesis of Oxa-, Thia-, and
 Selena[5]helicenes by Acetylene-Activated S<sub>N</sub>Ar Reactions.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4553
_journal_page_last               4559
_journal_paper_doi               10.1021/acs.joc.0c00052
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C26 H15 F S'
_chemical_formula_sum            'C26 H15 F S'
_chemical_formula_weight         378.47
_chemical_name_systematic
5-fluoro-2-phenylbenzo[5,6]phenanthro[4,3-b]thiophene
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-10-03
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.048(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8863(5)
_cell_length_b                   18.6245(7)
_cell_length_c                   7.6360(3)
_cell_measurement_reflns_used    9731
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      2.69
_cell_measurement_theta_min      27.05
_cell_volume                     1818.80(12)
_computing_cell_refinement       'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_collection       'APEX3 Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015b)'
_computing_structure_solution    'XT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      173.03
_diffrn.ambient_temp_esd         2.0
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker Photon 50'
_diffrn_measured_fraction_theta_full 0.9985
_diffrn_measured_fraction_theta_max 0.9985
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST ECO diffractometer'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_detector       'Bruker Photon 50'
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            26983
_diffrn_reflns_theta_full        27.0755
_diffrn_reflns_theta_max         27.08
_diffrn_reflns_theta_min         2.90
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Siemens KFFMO2K--90C'
_diffrn_standards_number         0
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3821
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             784.8399
_exptl_crystal_recrystallization_method
'vapor diffusion from chloroform-hexanes'
_exptl_crystal_size_max          0.73
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.2330
_refine_diff_density_min         -0.3075
_refine_diff_density_rms         0.0530
_refine_ls_d_res_high            0.7807
_refine_ls_d_res_low             7.0195
_refine_ls_goodness_of_fit_ref   0.9850
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3987
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9850
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.0539
_refine_ls_shift/su_mean         0.0108
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1P)^2^+0.3008P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1323
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              23
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                3485
_reflns_number_total             3987
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo0c00052_si_003.cif
_cod_data_source_block           JLKIII49_2_0ma_a
_cod_depositor_comments
'Adding full bibliography for 4038056--4038057.cif.'
_cod_original_sg_symbol_H-M      'P 2(1)/c'
_cod_database_code               4038057
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P),
 C00Q(H00Q), C00R(H00R), C00S(H00S)
;
_olex2_exptl_crystal_mounting_method 'paratone oil on a 500 micron loop'
_olex2_submission_original_sample_id JLKIII49_2_0ma_a
_olex2_submission_special_instructions 'No special instructions were received'