Copper-catalyzed atroposelective synthesis of C-O axially chiral compounds enabled by chiral 1,8-naphthyridine based ligands.
Dai, Lei; Zhou, Xueting; Guo, Jiami; Huang, Qingqin; Lu, Yixin; Chemical science 15 (2024) 5993–6001; doi:10.1039/d4sc01074d

data_1571261
_publ_section_title
;
 Copper-catalyzed atroposelective synthesis of C-O axially chiral
 compounds enabled by chiral 1,8-naphthyridine based ligands.
;
_journal_issue                   16
_journal_name_full               'Chemical science'
_journal_page_first              5993
_journal_page_last               6001
_journal_paper_doi               10.1039/d4sc01074d
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_sum            'C33 H31 N3 O'
_chemical_formula_weight         485.61
_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   geom
_atom_sites_solution_primary     'Dual Space'
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2023-12-27 deposited with the CCDC.	2024-03-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8263(4)
_cell_length_b                   11.6180(6)
_cell_length_c                   28.9031(15)
_cell_measurement_reflns_used    9733
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.97
_cell_measurement_theta_min      3.06
_cell_volume                     2628.0(2)
_computing_cell_refinement       'APEX4 v2021.10-1 (Bruker AXS)'
_computing_data_collection       'APEX4 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL--2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXT--(Sheldrick 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0099
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            129942
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.293
_diffrn_reflns_theta_min         3.058
_diffrn_source                   'Microfocus Sealed Tube'
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS-2016 (Bruker,2016). wR2(int)= 0.1226 before correction 
and =0.0410 after correction. 
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.251
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.063
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
; 
 Flack x determined using 2195 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         5185
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0251
_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^)+(0.0366P)^2^+0.4155P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0637
_refine_ls_wR_factor_ref         0.0639
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                5153
_reflns_number_total             5185
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01074d2.cif
_cod_data_source_block           N182
_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.

data item '_exptl_crystal_density_meas' value 'Not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1571261.cif.
;
_cod_database_code               1571261
_shelx_shelxl_version_number     2019/1
_computing_bruker_data_scaling   'SADABS V2016/2 (Bruker AXS Inc.)'
_shelx_res_checksum              92673