Enantioselective Construction of Bicyclic Pyran and Hydrindane Scaffolds via Intramolecular Rauhut–Currier Reactions Catalyzed by Thiourea-Phosphines
Li, Kaizhi; Jin, Zhichao; Chan, Wai-Lun; Lu, Yixin; ACS Catalysis 8 (2018) 8810–; doi:10.1021/acscatal.8b02706

data_4515707
_publ_section_title
;
 Enantioselective Construction of Bicyclic Pyran and Hydrindane Scaffolds
 via Intramolecular Rauhut--Currier Reactions Catalyzed by
 Thiourea-Phosphines
;
_journal_issue                   9
_journal_name_full               'ACS Catalysis'
_journal_page_first              8810
_journal_paper_doi               10.1021/acscatal.8b02706
_journal_volume                  8
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H15 N O5'
_chemical_formula_weight         313.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 113.464(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.4471(10)
_cell_length_b                   6.4084(3)
_cell_length_c                   12.0690(5)
_cell_measurement_reflns_used    9446
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.23
_cell_measurement_theta_min      3.99
_cell_volume                     1521.62(12)
_computing_cell_refinement       'APEX3 v2016.1-0 (Bruker AXS)'
_computing_data_collection       'APEX3 (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 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0422
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            27977
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.218
_diffrn_reflns_theta_min         3.993
_exptl_absorpt_coefficient_mu    0.849
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.301
_exptl_crystal_size_mid          0.249
_exptl_crystal_size_min          0.235
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
; 
 Flack x determined using 1300 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2902
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0247
_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^)+(0.0409P)^2^+0.4319P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0652
_refine_ls_wR_factor_ref         0.0653
_reflns_Friedel_coverage         0.819
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                2896
_reflns_number_total             2902
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b02706_si_001.cif
_cod_data_source_block           I432
_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/current/ACS/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 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4515707
_shelx_shelxl_version_number     2017/1
_computing_bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_shelx_res_checksum              28842
_shelx_hkl_checksum              46226