An asymmetric metal-templated route to amino acids with an isoquinolone core via a Rh(iii)-catalyzed coupling of aryl hydroxamates with chiral propargylglycine Ni(ii) complexes
Arsenov, Mikhail A.; Stoletova, Nadezhda V.; Savel'yeva, Tat'yana F.; Smol'yakov, Alexander F.; Maleev, Victor I.; Loginov, Dmitry A.; Larionov, Vladimir A.; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01970A

data_7158999
_publ_section_title
;
 An asymmetric metal-templated route to amino acids with an isoquinolone
 core via a Rh(iii)-catalyzed coupling of aryl hydroxamates with chiral
 propargylglycine Ni(ii) complexes
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01970A
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C45 H37 F3 N4 Ni O4, 0.5(C H Cl3)'
_chemical_formula_sum            'C45.5 H37.5 Cl1.5 F3 N4 Ni O4'
_chemical_formula_weight         873.18
_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     dual
_audit_creation_date             2022-08-16
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-08-24 deposited with the CCDC.	2022-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.529(2)
_cell_length_b                   19.627(3)
_cell_length_c                   31.278(4)
_cell_measurement_reflns_used    9844
_cell_measurement_temperature    120
_cell_measurement_theta_max      28.212
_cell_measurement_theta_min      2.21
_cell_volume                     9533(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1473
_diffrn_reflns_av_unetI/netI     0.0918
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            172297
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         1.464
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.545
_exptl_absorpt_correction_T_max  0.3803
_exptl_absorpt_correction_T_min  0.2599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1624 before and 0.1031 after correction.
The Ratio of minimum to maximum transmission is 0.6834.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description       plate
_exptl_crystal_F_000             3608
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.908
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.136
_refine_ls_abs_structure_details
;
 Flack x determined using 5249 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.139(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1051
_refine_ls_number_reflns         18714
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1194
_refine_ls_R_factor_gt           0.0998
_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^)+(0.1388P)^2^+50.8436P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2545
_refine_ls_wR_factor_ref         0.2693
_reflns_Friedel_coverage         0.839
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                14927
_reflns_number_total             18714
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01970a2.cif
_cod_data_source_block           sr_4ha
_cod_depositor_comments
;

2024-10-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C91 H75 Cl3 F6 N8 Ni2 O8'
_cod_original_formula_weight         1746.36
_cod_original_formula_moiety         '2(C45 H37 F3 N4 Ni O4), C H Cl3'
_cod_original_formula_units_Z            4
_cod_database_code               7158999
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C26B) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(F2B) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
3.a Ternary CH refined with riding coordinates:
 C34A(H34A), C36B(H36B), C1S(H1S)
3.b Secondary CH2 refined with riding coordinates:
 C13B(H13A,H13B), C3A(H3AA,H3AB), C13A(H13C,H13D), C40B(H40A,H40B), C36A(H36A,
 H36C), C35A(H35A,H35B), C37A(H37C,H37D), C37B(H37A,H37B), C38A(H38C,H38D),
 C3B(H3BA,H3BB), C38B(H38A,H38B), C39B(H39A,H39B)
3.c Aromatic/amide H refined with riding coordinates:
 C19A(H19A), C18A(H18A), C11B(H11B), C11A(H11A), N4B(H4B), C42B(H42B),
 C20B(H20B), C26A(H26A), C44A(H44A), C22A(H22A), C5A(H5A), C16B(H16B),
 C15A(H15A), C5B(H5B), C45A(H45A), N4A(H4A), C15B(H15B), C33B(H33B), C8A(H8A),
 C30A(H30A), C43B(H43B), C29A(H29A), C10A(H10A), C8B(H8B), C16A(H16A), C9B(H9B),
  C10B(H10B), C19B(H19B), C9A(H9A), C44B(H44B), C28A(H28A), C25A(H25A),
 C30B(H30B), C31A(H31A), C46B(H46B), C45B(H45B), C23A(H23A), C31B(H31B),
 C43A(H43A), C32B(H32B), C26B(H26B), C27B(H27B), C23B(H23B), C24B(H24B),
 C25B(H25B), C24A(H24A), C40A(H40C), C41A(H41A)
3.d Fitted hexagon refined as free rotating group:
 C26B(C27B,C22B,C23B,C24B,C25B)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              97041
_shelx_fab_checksum              36354
_olex2_submission_special_instructions 'No special instructions were received'