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_1552884
_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 H20 O'
_chemical_formula_sum            'C23 H20 O'
_chemical_formula_weight         312.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_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                 111.6606(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.3724(8)
_cell_length_b                   5.5677(3)
_cell_length_c                   18.8919(12)
_cell_measurement_reflns_used    6581
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      69.29
_cell_measurement_theta_min      4.35
_cell_volume                     1698.27(16)
_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 0.991
_diffrn_measured_fraction_theta_max 0.978
_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  0.0156
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            4368
_diffrn_reflns_point_group_measured_fraction_full 0.961
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_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.279
_diffrn_reflns_theta_min         2.956
_exptl_absorpt_coefficient_mu    0.562
_exptl_absorpt_correction_T_max  0.9369
_exptl_absorpt_correction_T_min  0.8379
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_description       Plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
; 
 Flack x determined using 1233 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.05(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         2996
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0301
_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^)+(0.0509P)^2^+0.4204P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0800
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    0.924
_reflns_Friedel_fraction_max     0.902
_reflns_number_gt                2931
_reflns_number_total             2996
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc05111b3.cif
_cod_data_source_block           JF2822FMI
_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_original_sg_symbol_H-M      'I 2'
_cod_database_code               1552884
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.877
_shelx_estimated_absorpt_t_max   0.966
_shelx_res_checksum              96318