Enantioselective deprotometalation of alkyl ferrocenecarboxylates using bimetallic bases
Dayaker, Gandrath; Erb, William; Hedidi, Madani; Chevallier, Floris; Blot, Marielle; Gros, Philippe C.; Hilmersson, Göran; Roisnel, Thierry; Dorcet, Vincent; Bentabed-Ababsa, Ghenia; Mongin, Florence; New Journal of Chemistry 45 (2021) 22579–22590; doi:10.1039/D1NJ04526A

data_7061073
_publ_section_title
;
 Enantioselective deprotometalation of alkyl ferrocenecarboxylates using
 bimetallic bases
;
_journal_issue                   48
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              22579
_journal_page_last               22590
_journal_paper_doi               10.1039/D1NJ04526A
_journal_volume                  45
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C18 H30 N, Cl'
_chemical_formula_sum            'C18 H30 Cl N'
_chemical_formula_weight         295.88
_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
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2021-09-16 deposited with the CCDC.	2021-11-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.636(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4383(9)
_cell_length_b                   10.9604(14)
_cell_length_c                   14.2059(13)
_cell_measurement_reflns_used    2278
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      21.56
_cell_measurement_theta_min      2.36
_cell_measurement_wavelength     0.71073
_cell_volume                     1760.8(3)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_molecular_graphics
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_structure_solution    'SIR97 (A. Altomare et al., 1999)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_orient_matrix_UB_11      -0.0524112
_diffrn_orient_matrix_UB_12      -0.0623085
_diffrn_orient_matrix_UB_13      0.0236617
_diffrn_orient_matrix_UB_21      -0.0588688
_diffrn_orient_matrix_UB_22      0.0650731
_diffrn_orient_matrix_UB_23      0.0081885
_diffrn_orient_matrix_UB_31      -0.0400066
_diffrn_orient_matrix_UB_32      -0.0141253
_diffrn_orient_matrix_UB_33      -0.0666516
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0957
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13274
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_min         3.096
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.116
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
Flack x determined using 1586 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         7320
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0533
_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^)+(0.0401P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1121
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    0.853
_reflns_Friedel_fraction_max     0.813
_reflns_number_gt                5011
_reflns_number_total             7320
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1nj04526a2.cif
_cod_data_source_block           DG181C
_cod_depositor_comments
'Adding full bibliography for 7061069--7061073.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7061073
_shelx_res_checksum              26401