Enantioselective copper-catalyzed B-H bond insertion reaction of α-diazo phosphonates to access chiral α-boryl phosphonates.
Li, Longlong; Yu, Kui; An, Hejun; Cai, Xinping; Song, Qiuling; Chemical science 15 (2024) 7130–7135; doi:10.1039/d4sc01271b

data_1571425
_publ_section_title
;
 Enantioselective copper-catalyzed B-H bond insertion reaction of
 &#x3b1;-diazo phosphonates to access chiral &#x3b1;-boryl phosphonates.
;
_journal_issue                   19
_journal_name_full               'Chemical science'
_journal_page_first              7130
_journal_page_last               7135
_journal_paper_doi               10.1039/d4sc01271b
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H27 B O3 P2'
_chemical_formula_sum            'C22 H27 B O3 P2'
_chemical_formula_weight         412.18
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-12-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2023-12-07 deposited with the CCDC.	2024-04-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.183(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.778(2)
_cell_length_b                   9.8031(17)
_cell_length_c                   11.594(3)
_cell_measurement_reflns_used    9583
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      29.013
_cell_measurement_theta_min      2.879
_cell_volume                     1089.7(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.842
_diffrn_measurement_device_type  'BrukerD8 venture microsource'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.842
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20561
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.751
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.890
_diffrn_reflns_theta_min         1.975
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6499
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.014
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Flack x determined using 1839 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         5636
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0470P)^2^+0.2648P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.1020
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.650
_reflns_number_gt                4743
_reflns_number_total             5636
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01271b2.cif
_cod_data_source_block           lll00011_0m
_cod_depositor_comments          'Adding full bibliography for 1571425.cif.'
_cod_original_cell_volume        1089.8(4)
_cod_database_code               1571425
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.968
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00J(H00J)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C008(H008), C009(H009), C00C(H00C), C00D(H00D), C00E(H00E),
 C00F(H00F), C00G(H00G), C00H(H00H), C00K(H00K), C00L(H00L), C00N(H00P),
 C00O(H00Q), C00P(H00R), C00Q(H00S)
2.c Idealised Me refined as rotating group:
 C00I(H00A,H00B,H00I), C00M(H00M,H00N,H00O), C00S(H00V,H00W,H00X)
;
_shelx_res_checksum              94936
_olex2_submission_special_instructions 'No special instructions were received'