Efficient synthesis of chiral γ-aminobutyric esters via direct rhodium-catalysed enantioselective hydroaminomethylation of acrylates
Cunillera, Anton; de los Bernardos, Miriam Díaz; Urrutigoïty, Martine; Claver, Carmen; Ruiz, Aurora; Godard, Cyril; Catalysis Science & Technology 10 (2020) 630–634; doi:10.1039/C9CY01797F

data_1557058
_publ_section_title
;
 Efficient synthesis of chiral \g-aminobutyric esters via direct
 rhodium-catalysed enantioselective hydroaminomethylation of acrylates
;
_journal_issue                   3
_journal_name_full               'Catalysis Science &amp; Technology'
_journal_page_first              630
_journal_page_last               634
_journal_paper_doi               10.1039/C9CY01797F
_journal_volume                  10
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C36.5 H57 B Cl F4 N4 P4 Rh'
_chemical_formula_weight         900.91
_space_group_IT_number           152
_space_group_name_Hall           'P 31 2"'
_space_group_name_H-M_alt        'P 31 2 1'
_symmetry_cell_setting           trigonal
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-09-05 deposited with the CCDC.	2020-01-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   13.824(3)
_cell_length_b                   13.824(3)
_cell_length_c                   40.089(8)
_cell_measurement_reflns_used    9834
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.67
_cell_measurement_theta_min      2.29
_cell_volume                     6635(2)
_computing_cell_refinement       'Bruker APEX2 v2014.9-0'
_computing_data_collection       'Bruker APEX2 v2014.9-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    Sir2011
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            58300
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.034
_diffrn_reflns_theta_min         1.524
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_current           0.6
_diffrn_source_power             50
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_source_type              'Bruker APEX DUO'
_exptl_absorpt_coefficient_mu    0.638
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       block
_exptl_crystal_F_000             2802
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.493
_refine_diff_density_min         -0.734
_refine_diff_density_rms         0.106
_refine_ls_abs_structure_details
;
 Flack x determined using 3582 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     885
_refine_ls_number_reflns         11429
_refine_ls_number_restraints     1215
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0567
_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^)+(0.0621P)^2^+8.4450P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1458
_reflns_Friedel_coverage         0.772
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.955
_reflns_number_gt                9617
_reflns_number_total             11429
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cy01797f2.cif
_cod_data_source_block           mo_ACM497_0m
_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.

data item '_symmetry_cell_setting' value 'Trigonal' was changed to
'trigonal' 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 1557058--1557059.cif.

 Adding full bibliography for 1557058--1557059.cif.
;
_cod_original_cell_volume        6635(3)
_cod_original_formula_sum        'C36.50 H57 B Cl F4 N4 P4 Rh'
_cod_database_code               1557058
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.939
_shelx_estimated_absorpt_t_max   0.969
_shelx_res_checksum              35007