Asymmetric Synthesis of P-Stereogenic Compounds via Thulium(III)-Catalyzed Desymmetrization of Dialkynylphosphine Oxides
Zhang, Yu; Zhang, Fengcai; Chen, Long; Xu, Jian; Liu, Xiaohua; Feng, Xiaoming; ACS Catalysis 9 (2019) 4834–; doi:10.1021/acscatal.9b00860

data_4514778
_publ_section_title
;
 Asymmetric Synthesis of P-Stereogenic Compounds via
 Thulium(III)-Catalyzed Desymmetrization of Dialkynylphosphine Oxides
;
_journal_issue                   6
_journal_name_full               'ACS Catalysis'
_journal_page_first              4834
_journal_paper_doi               10.1021/acscatal.9b00860
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration syn
_chemical_formula_sum            'C51 H84 F9 N4 O18 Pr S3'
_chemical_formula_weight         1449.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 101.368(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.1823(13)
_cell_length_b                   16.5445(19)
_cell_length_c                   16.4080(19)
_cell_measurement_reflns_used    9917
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      2.76
_cell_volume                     3242.2(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            43205
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.409
_diffrn_reflns_theta_min         2.760
_exptl_absorpt_coefficient_mu    0.941
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6471
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1500
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.080
_refine_diff_density_max         1.287
_refine_diff_density_min         -0.927
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details
;
 Flack x determined using 6463 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     780
_refine_ls_number_reflns         15913
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0619P)^2^+2.6963P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1141
_reflns_Friedel_coverage         0.910
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                14852
_reflns_number_total             15913
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b00860_si_004.cif
_cod_data_source_block           mo_ZY_20180919_Pr_0m_b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-Scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4514778
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.746
_shelx_estimated_absorpt_t_max   0.928
_shelx_res_checksum              3038
_shelx_hkl_checksum              2112