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_7129926
_publ_section_title
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 Facile access to chiral chromanone-2-carboxylic acids enabled by
 Rhodium-catalyzed chemo- and enantioselective hydrogenation
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_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC00589A
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H10 O4'
_chemical_formula_sum            'C10 H10 O4'
_chemical_formula_weight         194.18
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-12
_audit_creation_method
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
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_audit_update_record
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2021-11-15 deposited with the CCDC.	2022-03-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.031(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4217(16)
_cell_length_b                   5.7877(7)
_cell_length_c                   12.7894(17)
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    200.00
_cell_measurement_theta_max      56.996
_cell_measurement_theta_min      3.099
_cell_volume                     892.0(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_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  0.0374
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14204
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         56.997
_diffrn_reflns_theta_min         3.099
_diffrn_source_current           2.23
_diffrn_source_power             0.1557878
_diffrn_source_voltage           69.86
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.606
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.6022
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1220 before and 0.0561 after correction.
The Ratio of minimum to maximum transmission is 0.8017.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_description       needle
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1413 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3518
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0276
_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^)+(0.0363P)^2^+0.1040P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0703
_refine_ls_wR_factor_ref         0.0712
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_full    0.962
_reflns_Friedel_fraction_max     0.934
_reflns_number_gt                3381
_reflns_number_total             3518
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00589a2.cif
_cod_data_source_block           20211112al_0m_a
_cod_database_code               7129926
_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.a Ternary CH refined with riding coordinates:
 C9(H9), C11(H11), C16(H16), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C13(H13), C14(H14), C15(H15), C18(H18), C19(H19), C1A(H1A)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4), O8(H8), O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'