Machine-Learning-Assisted Synthesis of Polar Racemates.
Nisbet, Matthew L.; Pendleton, Ian M.; Nolis, Gene M.; Griffith, Kent J.; Schrier, Joshua; Cabana, Jordi; Norquist, Alexander J.; Poeppelmeier, Kenneth R.; Journal of the American Chemical Society 142 (2020) 7555–7566; doi:10.1021/jacs.0c01239

data_4134676
_publ_section_title
;
 Machine-Learning-Assisted Synthesis of Polar Racemates.
;
_journal_issue                   16
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7555
_journal_page_last               7566
_journal_paper_doi               10.1021/jacs.0c01239
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C20 H18 Cu N4 O, F6 Zr, 1.5(O)'
_chemical_formula_sum            'C20 H18 Cu F6 N4 O2.5 Zr'
_chemical_formula_weight         623.14
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.5390(19)
_cell_length_b                   14.8908(14)
_cell_length_c                   15.0531(15)
_cell_measurement_reflns_used    9787
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.40
_cell_measurement_theta_min      3.38
_cell_volume                     4603.9(8)
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2017)'
_computing_data_collection       'APEX2 V2017.3 (Bruker, 2017)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      99.93
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'MX optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            276593
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.417
_diffrn_reflns_theta_min         1.689
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    1.453
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.6958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0651 before and 0.0616 after correction. The Ratio of minimum to maximum transmission is 0.9313. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.798
_exptl_crystal_description       block
_exptl_crystal_F_000             2472
_exptl_crystal_size_max          0.429
_exptl_crystal_size_mid          0.358
_exptl_crystal_size_min          0.316
_refine_diff_density_max         1.667
_refine_diff_density_min         -1.381
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details
;
 Flack x determined using 9739 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0219(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     634
_refine_ls_number_reflns         22418
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0317
_refine_ls_shift/su_max          0.064
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0340P)^2^+4.7444P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.0800
_reflns_Friedel_coverage         0.936
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                21382
_reflns_number_total             22418
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c01239_si_009.cif
_cod_data_source_block           work
_cod_depositor_comments
'Adding full bibliography for 4134676--4134681.cif.'
_cod_original_formula_sum        'C20 H18 Cu F6 N4 O2.50 Zr'
_cod_database_code               4134676
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.657
_shelx_estimated_absorpt_t_min   0.575
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Sof(O7)=1-FVAR(1)
 Sof(O6)=FVAR(1)
3.a Rotating group:
 O2(H2A,H2B), O1(H1A,H1B)
3.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C22(H22), C23(H23), C24(H24), C27(H27), C28(H28), C29(H29),
 C30(H30), C31(H31), C32(H32), C33(H33), C34(H34), C37(H37), C38(H38), C39(H39),
  C40(H40), C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10),
 C11(H11), C12(H12), C13(H13), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20)
;
_shelx_res_checksum              27313
_shelx_hkl_checksum              63133
_shelx_fab_checksum              73716
_olex2_submission_original_sample_id MLN60E
_olex2_submission_special_instructions 'No special instructions were received'