Enantioselective Suzuki cross-coupling of 1,2-diboryl cyclopropanes.
Teresa, Javier; Velado, Marina; Fernández de la Pradilla, Roberto; Viso, Alma; Lozano, Blanca; Tortosa, Mariola; Chemical science 14 (2023) 1575–1581; doi:10.1039/d2sc05789a

data_1568272
_publ_section_title
;
 Enantioselective Suzuki cross-coupling of 1,2-diboryl cyclopropanes.
;
_journal_issue                   6
_journal_name_full               'Chemical science'
_journal_page_first              1575
_journal_page_last               1581
_journal_paper_doi               10.1039/d2sc05789a
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_sum            'C26 H21 Br2 N O2'
_chemical_formula_weight         539.26
_chemical_name_systematic
'(1R,2S,3R)-2-methyl-3-(1-methyl-1H-indol-5-yl)-2-phenylcyclopropyl 3,5-dibromobenzoate'
_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
_audit_update_record
;
2022-07-18 deposited with the CCDC.	2023-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.609(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6562(7)
_cell_length_b                   23.5435(18)
_cell_length_c                   11.2698(9)
_cell_measurement_reflns_used    9045
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      20.7894
_cell_measurement_theta_min      2.9264
_cell_volume                     2276.5(3)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1328)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            73125
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.17
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    3.584
_exptl_absorpt_correction_T_max  0.67
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1080
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.124
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.441
_refine_ls_abs_structure_details
;

Flack x determined using 2732 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.006(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     563
_refine_ls_number_reflns         8334
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0319
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0272P)^2^+1.1307P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0627
_refine_ls_wR_factor_ref         0.0698
_reflns_number_gt                6626
_reflns_number_total             8334
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05789a2.cif
_cod_data_source_block           03534_grande
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 1568272.cif.
;
_cod_database_code               1568272
_shelx_res_checksum              12411
_shelx_hkl_checksum              2989