Chasing the Elusive Benzofuran Impurity of the THR Antagonist NH-3: Synthesis, Isotope Labeling, and Biological Activity.
Singh, Latika; Pressly, Brandon; Mengeling, Brenda J.; Fettinger, James C.; Furlow, J. David; Lein, Pamela J.; Wulff, Heike; Singh, Vikrant; The Journal of organic chemistry 81 (2016) 1870–1876; doi:10.1021/acs.joc.5b02665

data_4036544
_publ_section_title
;
 Chasing the Elusive Benzofuran Impurity of the THR Antagonist NH-3:
 Synthesis, Isotope Labeling, and Biological Activity.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1870
_journal_page_last               1876
_journal_paper_doi               10.1021/acs.joc.5b02665
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C28 H27 N O6, C H Cl3'
_chemical_formula_sum            'C29 H28 Cl3 N O6'
_chemical_formula_weight         592.87
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 91.4288(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   40.9253(8)
_cell_length_b                   5.52760(10)
_cell_length_c                   24.9684(5)
_cell_measurement_reflns_used    9914
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      73.44
_cell_measurement_theta_min      5.66
_cell_volume                     5646.56(19)
_computing_cell_refinement       'SAINT (8.34a) (Bruker, 2013)'
_computing_data_collection       'Apex2 (2014.9-1) (Bruker, 2014)'
_computing_data_reduction        'SAINT (8.34a) (Bruker, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -50
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            14463
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.437
_diffrn_reflns_theta_min         3.541
_exptl_absorpt_coefficient_mu    3.307
_exptl_absorpt_correction_T_max  0.7618
_exptl_absorpt_correction_T_min  0.6229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5 (Sheldrick, 2014)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_description       Rod
_exptl_crystal_F_000             2464
_exptl_crystal_size_max          0.329
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.602
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     402
_refine_ls_number_reflns         5463
_refine_ls_number_restraints     52
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0510P)^2^+6.9907P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1087
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4866
_reflns_number_total             5463
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02665_si_003.cif
_cod_data_source_block           JF2452FMI
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4036544
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.409
_shelx_estimated_absorpt_t_max   0.885
_shelx_res_checksum              69853
_shelx_hkl_checksum              29880