Enantioselective synthesis of isochromans and tetrahydroisoquinolines by C-H insertion of donor/donor carbenes.
Nickerson, Leslie A.; Bergstrom, Benjamin D.; Gao, Mingchun; Shiue, Yuan-Shin; Laconsay, Croix J.; Culberson, Matthew R.; Knauss, Walker A.; Fettinger, James C.; Tantillo, Dean J.; Shaw, Jared T.; Chemical science 11 (2020) 494–498; doi:10.1039/c9sc05111b

data_1552886
_publ_section_title
;
 Enantioselective synthesis of isochromans and tetrahydroisoquinolines by
 C-H insertion of donor/donor carbenes.
;
_journal_issue                   2
_journal_name_full               'Chemical science'
_journal_page_first              494
_journal_page_last               498
_journal_paper_doi               10.1039/c9sc05111b
_journal_volume                  11
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H19 N O2'
_chemical_formula_sum            'C23 H19 N O2'
_chemical_formula_weight         341.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-06-28 deposited with the CCDC.	2019-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5431(2)
_cell_length_b                   17.2727(6)
_cell_length_c                   17.7127(6)
_cell_measurement_reflns_used    9462
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.09
_cell_measurement_theta_min      2.56
_cell_volume                     1695.89(10)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Photon100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10237
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.081
_diffrn_reflns_theta_min         3.574
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_T_max  0.9370
_exptl_absorpt_correction_T_min  0.8744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       Block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.076
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
; 
 Flack x determined using 1342 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.08(6)
_refine_ls_extinction_coef       0.0042(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   1.043
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         3335
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0250
_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^)+(0.0378P)^2^+0.3293P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0645
_refine_ls_wR_factor_ref         0.0651
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3267
_reflns_number_total             3335
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc05111b3.cif
_cod_data_source_block           JF2831FMI
_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 6909 2019-04-08 15:41:33Z antanas 

 Adding full bibliography for 1552883--1552886.cif.

 Adding full bibliography for 1552883--1552886.cif.
;
_cod_database_code               1552886
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.869
_shelx_estimated_absorpt_t_max   0.950
_shelx_res_checksum              42689