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_7061069
_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 rm/ad/rmad/syn/unk/.
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C25 H30 N2 O3'
_chemical_formula_sum            'C25 H30 N2 O3'
_chemical_formula_weight         406.51
_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
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4497(2)
_cell_length_b                   15.2211(5)
_cell_length_c                   19.6694(6)
_cell_measurement_reflns_used    4668
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.05
_cell_measurement_theta_min      2.47
_cell_measurement_wavelength     0.71073
_cell_volume                     2230.36(12)
_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, 2020)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_orient_matrix_UB_11      0.1283597
_diffrn_orient_matrix_UB_12      0.0054145
_diffrn_orient_matrix_UB_13      -0.0142730
_diffrn_orient_matrix_UB_21      -0.0218035
_diffrn_orient_matrix_UB_22      -0.0426087
_diffrn_orient_matrix_UB_23      -0.0378067
_diffrn_orient_matrix_UB_31      -0.0326675
_diffrn_orient_matrix_UB_32      0.0497135
_diffrn_orient_matrix_UB_33      -0.0308491
_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  0.0383
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14181
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_min         1.692
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.881
_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    1.211
_exptl_crystal_description       fragment
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
Flack x determined using 1567 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.8(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4968
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.170
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0402P)^2^+0.2401P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.1042
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                4331
_reflns_number_total             4968
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1nj04526a2.cif
_cod_data_source_block           DG180F1
_cod_depositor_comments
'Adding full bibliography for 7061069--7061073.cif.'
_cod_original_cell_volume        2230.37(12)
_cod_database_code               7061069
_shelx_res_checksum              74259