Organocatalytic hydroboration of olefins in pyrrolidinium ionic liquids
Huninik, Paweł; Szyling, Jakub; Czapik, Agnieszka; Walkowiak, Jędrzej; Green Chemistry 25 (2023) 3715–3722; doi:10.1039/D2GC04163D

data_7246660
_publ_section_title
;
 Organocatalytic hydroboration of olefins in pyrrolidinium ionic liquids
;
_journal_issue                   9
_journal_name_full               'Green Chemistry'
_journal_page_first              3715
_journal_page_last               3722
_journal_paper_doi               10.1039/D2GC04163D
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C16 H25 B O4'
_chemical_formula_sum            'C16 H25 B O4'
_chemical_formula_weight         292.17
_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     direct
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-11-01 deposited with the CCDC.	2023-03-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.899(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4643(2)
_cell_length_b                   21.3155(7)
_cell_length_c                   11.9798(4)
_cell_measurement_reflns_used    8028
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.4470
_cell_measurement_theta_min      3.6920
_cell_volume                     1649.79(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.118a'
_computing_data_collection       'CrysAlisPro 1.171.41.118a'
_computing_data_reduction        'CrysAlisPro 1.171.41.118a'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12931
_diffrn_reflns_point_group_measured_fraction_full 0.867
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.218
_diffrn_reflns_theta_min         3.692
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.118a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_description       irregular
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.647
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details
;
 Flack x determined using 1912 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.41(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         5241
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0686
_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^)+(0.1281P)^2^+0.8994P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1812
_refine_ls_wR_factor_ref         0.1823
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_full    0.729
_reflns_Friedel_fraction_max     0.726
_reflns_number_gt                5091
_reflns_number_total             5241
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc04163d2.cif
_cod_data_source_block           DATA
_cod_depositor_comments          'Adding full bibliography for 7246660.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7246660
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.735
_shelx_estimated_absorpt_t_max   0.968
_shelx_res_checksum              30933