Facile access to chiral chromanone-2-carboxylic acids enabled by Rhodium-catalyzed chemo- and enantioselective hydrogenation
Nie, Zhuang; Liu, Song; Wang, Tonglin; Shen, Zhanhong; Nie, Huifang; Xi, Jiayue; Zhang, Dongxu; Zheng, Xiao Hui; Zhang, Shengyong; Yao, Lin; Chemical Communications  (2022) –; doi:10.1039/D2CC00589A

data_7129925
_publ_section_title
;
 Facile access to chiral chromanone-2-carboxylic acids enabled by
 Rhodium-catalyzed chemo- and enantioselective hydrogenation
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC00589A
_journal_year                    2022
_chemical_formula_moiety         'C10 H6 Br O4'
_chemical_formula_sum            'C10 H5 Br O4'
_chemical_formula_weight         269.05
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-06-14 deposited with the CCDC.	2022-03-30 downloaded from the CCDC.
;
_cell_angle_alpha                61.559(2)
_cell_angle_beta                 86.409(2)
_cell_angle_gamma                78.824(2)
_cell_formula_units_Z            2
_cell_length_a                   5.1151(4)
_cell_length_b                   10.2380(7)
_cell_length_c                   10.7004(8)
_cell_measurement_reflns_used    7560
_cell_measurement_temperature    195(2)
_cell_measurement_theta_max      52.989
_cell_measurement_theta_min      4.090
_cell_volume                     483.10(6)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      195.0
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6954
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        52.990
_diffrn_reflns_theta_max         52.990
_diffrn_reflns_theta_min         4.334
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.953
_exptl_absorpt_correction_T_max  0.7505
_exptl_absorpt_correction_T_min  0.4010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1207 before and 0.0711 after correction. The Ratio of minimum to maximum transmission is 0.5343. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.850
_exptl_crystal_description       plate
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.792
_refine_diff_density_min         -0.766
_refine_diff_density_rms         0.142
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.274
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1680
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.287
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0623
_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^)+4.7410P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1685
_refine_ls_wR_factor_ref         0.1685
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1673
_reflns_number_total             1680
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00589a2.cif
_cod_data_source_block           20210611_5_0m_a
_cod_database_code               7129925
_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
 At 1.5 times of:
  All O(H) groups
2. Rigid bond restraints
 C2, C8, C9, C10, C10', O2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C2 \\sim C8 \\sim C9 \\sim C10 \\sim C10' \\sim O2: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(C10')=Sof(H10C)=Sof(H10D)=1-FVAR(1)
 Sof(C10)=Sof(H10A)=Sof(H10B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C10'(H10C,H10D)
5.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4A), C7(H7)
5.c Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_shelx_res_checksum              50904
_olex2_submission_special_instructions 'No special instructions were received'