Tandem process of asymmetric organocatalysis and selective post-functionalization: enantiodivergent synthesis of bioactive indane-1-carboxylic acid derivatives.
Zhanabaeva, Madina; Kovalevsky, Ruslan A.; Kucherenko, Alexander S.; Korlyukov, Alexander A.; Zlotin, Sergei G.; Organic & biomolecular chemistry 23 (2025) 5611–5615; doi:10.1039/d5ob00551e

data_7160529
_publ_section_title
;
 Tandem process of asymmetric organocatalysis and selective
 post-functionalization: enantiodivergent synthesis of bioactive
 indane-1-carboxylic acid derivatives.
;
_journal_issue                   23
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5611
_journal_page_last               5615
_journal_paper_doi               10.1039/d5ob00551e
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H7 F O3'
_chemical_formula_sum            'C10 H7 F O3'
_chemical_formula_weight         194.16
_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             2024-09-30
_audit_creation_method
;
Olex2 1.5
(compiled 2023.11.24 svn.r209d9fb for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-01-07 deposited with the CCDC.	2025-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.0058(9)
_cell_length_b                   14.041(2)
_cell_length_c                   19.541(3)
_cell_measurement_reflns_used    1948
_cell_measurement_temperature    120
_cell_measurement_theta_max      19.795
_cell_measurement_theta_min      2.901
_cell_volume                     1647.8(4)
_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  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0923
_diffrn_reflns_av_unetI/netI     0.1291
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            20899
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.530
_diffrn_reflns_theta_min         1.786
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1581 before and 0.0680 after correction.
The Ratio of minimum to maximum transmission is 0.7858.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_description       rhombohedral
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 1003 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.0(9)
_refine_ls_extinction_coef       0.0099(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         5037
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.976
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0543
_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^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1124
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3234
_reflns_number_total             5037
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00551e2.cif
_cod_data_source_block           ruskov2
_cod_depositor_comments          'Adding full bibliography for 7160529.cif.'
_cod_database_code               7160529
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.958
_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:
 C1(H1A), C1A(H1AB)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C2A(H2AA,H2AB)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C5A(H5A), C7A(H7A), C8A(H8A)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O1A(H1AA)
;
_shelx_res_checksum              14453
_olex2_submission_special_instructions 'No special instructions were received'