Divergent stereochemical outcomes in the insertion of donor/donor carbenes into the C–H bonds of stereogenic centers
Dishman, Sarah N.; Laconsay, Croix J.; Fettinger, James C.; Tantillo, Dean J.; Shaw, Jared T.; Chemical Science 13 (2022) 1030–1036; doi:10.1039/D1SC04622E

data_1565822
_publ_section_title
;
 Divergent stereochemical outcomes in the insertion of donor/donor
 carbenes into the C--H bonds of stereogenic centers
;
_journal_issue                   4
_journal_name_full               'Chemical Science'
_journal_page_first              1030
_journal_page_last               1036
_journal_paper_doi               10.1039/D1SC04622E
_journal_volume                  13
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H20 I N O2'
_chemical_formula_sum            'C23 H20 I N O2'
_chemical_formula_weight         469.30
_chemical_name_systematic
Trans-N-(4-iodophenyl)-2-2-methyl-3-phenyl-2,3-dihydrobenzofuran-2-yl)acetamide
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-07-12 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                99.2233(18)
_cell_angle_beta                 96.0361(18)
_cell_angle_gamma                91.1970(17)
_cell_formula_units_Z            2
_cell_length_a                   8.7754(5)
_cell_length_b                   8.8984(6)
_cell_length_c                   12.8772(8)
_cell_measurement_reflns_used    9172
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.68
_cell_measurement_theta_min      2.34
_cell_volume                     986.31(11)
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_collection       'Apex3 (2017.3) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Photon100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            49290
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_min         2.336
_exptl_absorpt_coefficient_mu    1.641
_exptl_absorpt_correction_T_max  0.8365
_exptl_absorpt_correction_T_min  0.7842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_description       Plate
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.308
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
; 
 Flack x determined using 5250 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.034(4)
_refine_ls_extinction_coef       0.0076(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     530
_refine_ls_number_reflns         11503
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0217
_refine_ls_R_factor_gt           0.0194
_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^)+(0.0165P)^2^+0.3992P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0399
_refine_ls_wR_factor_ref         0.0408
_reflns_Friedel_coverage         0.997
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                10996
_reflns_number_total             11503
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc04622e2.cif
_cod_data_source_block           JF2873FF
_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/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 1565821--1565823.cif.
;
_cod_database_code               1565822
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              73133
_shelx_hkl_checksum              36805