Nine-Membered Benzofuran-Fused Heterocycles: Enantioselective Synthesis by Pd-Catalysis and Rearrangement via Transannular Bond Formation.
Rong, Zi-Qiang; Yang, Li-Cheng; Liu, Song; Yu, Zhaoyuan; Wang, Ya-Nong; Tan, Zher Yin; Huang, Rui-Zhi; Lan, Yu; Zhao, Yu; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b09161

data_4126631
_publ_section_title
;
 Nine-Membered Benzofuran-Fused Heterocycles: Enantioselective Synthesis
 by Pd-Catalysis and Rearrangement via Transannular Bond Formation.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b09161
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C36 H28 Cl N O5 S'
_chemical_formula_sum            'C36 H28 Cl N O5 S'
_chemical_formula_weight         622.10
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 101.8790(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.5856(5)
_cell_length_b                   9.1759(4)
_cell_length_c                   14.3288(6)
_cell_measurement_reflns_used    4477
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.526
_cell_measurement_theta_min      3.152
_cell_volume                     1490.65(11)
_computing_cell_refinement
'SHELXTL, Acta Cryst., Sect. A 2008, 64, 112-122.'
_computing_data_collection       'APEX3 v2016.5.0'
_computing_data_reduction        'Saint, APEX v2014.11.0.'
_computing_molecular_graphics    Ortep3
_computing_publication_material  'APEX3 v2016.5.0'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT, Acta Cryst., Sect. A 2015, A71, 3-8.'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker AXS D8 Venture '
_diffrn_measurement_method       'profile data from \q/2\q scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33217
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.526
_diffrn_reflns_theta_min         3.152
_exptl_absorpt_coefficient_mu    2.168
_exptl_absorpt_correction_T_max  0.603
_exptl_absorpt_correction_T_min  0.361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       'prism '
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.590
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.260
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 2501 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.047(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         5712
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0236
_refine_ls_R_factor_gt           0.0235
_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^)+(0.0401P)^2^+0.1766P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0645
_refine_ls_wR_factor_ref         0.0646
_reflns_Friedel_coverage         0.813
_reflns_Friedel_fraction_full    0.939
_reflns_Friedel_fraction_max     0.927
_reflns_number_gt                5660
_reflns_number_total             5712
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b09161_si_003.cif
_cod_data_source_block           g786
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_absolute_configuration' value 'AD' changed to 'ad'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-Scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4126631
_shelx_estimated_absorpt_t_min   0.361
_shelx_estimated_absorpt_t_max   0.603
_shelx_res_checksum              97560
_shelx_hkl_checksum              87632