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_1565823
_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         'C33 H27 N O3'
_chemical_formula_sum            'C33 H27 N O3'
_chemical_formula_weight         485.55
_chemical_name_systematic
1-hydroxy-N-(4-((2R,3S)-2-methyl-2-phenyl-2,3-dihydrobenzofurna-3-yl)benzyl)-2-napthamide
_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   difmap
_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                85.4422(16)
_cell_angle_beta                 85.4490(17)
_cell_angle_gamma                86.8128(17)
_cell_formula_units_Z            2
_cell_length_a                   6.3151(4)
_cell_length_b                   11.1980(7)
_cell_length_c                   17.7567(10)
_cell_measurement_reflns_used    9992
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      69.49
_cell_measurement_theta_min      3.97
_cell_volume                     1246.24(13)
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_collection       'Apex2 (2014.9-1) (Bruker, 2014)'
_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      90(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.939
_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  0.0229
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20993
_diffrn_reflns_point_group_measured_fraction_full 0.909
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.434
_diffrn_reflns_theta_min         2.503
_exptl_absorpt_coefficient_mu    0.653
_exptl_absorpt_correction_T_max  0.8692
_exptl_absorpt_correction_T_min  0.7714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       Block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.491
_exptl_crystal_size_mid          0.283
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
; 
 Flack x determined using 3857 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.05(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     883
_refine_ls_number_reflns         8303
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0289
_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^)+(0.0585P)^2^+0.1182P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0778
_reflns_Friedel_coverage         0.888
_reflns_Friedel_fraction_full    0.862
_reflns_Friedel_fraction_max     0.834
_reflns_number_gt                8280
_reflns_number_total             8303
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc04622e2.cif
_cod_data_source_block           JF2920F
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_absolute_configuration' value 'AD' was changed
to 'ad' 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.

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               1565823
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.740
_shelx_estimated_absorpt_t_max   0.932
_shelx_res_checksum              67713
_shelx_hkl_checksum              84422