Exploration of flow reaction conditions using machine-learning for enantioselective organocatalyzed Rauhut-Currier and [3+2] annulation sequence.
Kondo, Masaru; Wathsala, H. D. P.; Sako, Makoto; Hanatani, Yutaro; Ishikawa, Kazunori; Hara, Satoshi; Takaai, Takayuki; Washio, Takashi; Takizawa, Shinobu; Sasai, Hiroaki; Chemical communications (Cambridge, England) 56 (2020) 1259–1262; doi:10.1039/c9cc08526b

data_7125902
_publ_section_title
;
 Exploration of flow reaction conditions using machine-learning for
 enantioselective organocatalyzed Rauhut-Currier and [3+2] annulation
 sequence.
;
_journal_issue                   8
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1259
_journal_page_last               1262
_journal_paper_doi               10.1039/c9cc08526b
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C28 H27 N O6 S'
_chemical_formula_sum            'C28 H27 N O6 S'
_chemical_formula_weight         505.58
_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     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2019-04-15 deposited with the CCDC.	2019-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   9.34005(17)
_cell_length_b                   9.81274(18)
_cell_length_c                   26.8301(19)
_cell_measurement_reflns_used    40513
_cell_measurement_temperature    150
_cell_measurement_theta_max      68.31
_cell_measurement_theta_min      3.29
_cell_volume                     2459.02(19)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2017)'
_computing_structure_refinement  'SHELXL Version 2017/1 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID 191R'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            48371
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.248
_diffrn_reflns_theta_min         3.294
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.547
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_correction_T_min  0.793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1064.00
_exptl_crystal_size_max          0.091
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.24
_refine_ls_abs_structure_details
;
 Flack x determined using 1625 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.006(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4509
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0448P)^2^+0.5304P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0824
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4196
_reflns_number_total             4509
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c9cc08526b2.cif
_cod_data_source_block           No9_1_2
_cod_original_cell_volume        2459.01(18)
_cod_database_code               7125902
_shelx_res_checksum              52450