Mechanistic insights for the transprotection of tertiary amines with Boc2O via charged carbamates: access to both enantiomers of 2-azanorbornane-3-exo-carboxylic acids
Sampaio-Dias, Ivo E.; Silva-Reis, Sara C.; Pinto da Silva, Luís; García-Mera, Xerardo; Maestro, Miguel A.; Rodríguez-Borges, José E.; Organic Chemistry Frontiers 6 (2019) 3540–; doi:10.1039/C9QO00957D

data_1555150
_publ_section_title
;
 Mechanistic insights for the transprotection of tertiary amines with
 Boc2O via charged carbamates: access to both enantiomers of
 2-azanorbornane-3-exo-carboxylic acids
;
_journal_issue                   20
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3540
_journal_paper_doi               10.1039/C9QO00957D
_journal_volume                  6
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H34 N O2, C2 F3 O2, 0.25(H2 O)'
_chemical_formula_sum            'C25 H34.5 F3 N O1.25'
_chemical_formula_weight         474.04
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2018-03-19 deposited with the CCDC.	2019-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 123.325(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.6626(8)
_cell_length_b                   10.3356(4)
_cell_length_c                   13.6724(5)
_cell_measurement_reflns_used    40520?
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      52.471
_cell_measurement_theta_min      4.593
_cell_volume                     2439.76(17)
_computing_cell_refinement
'SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite.'
_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_data_reduction
'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_molecular_graphics
'Bruker SHEXTL Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_publication_material
'Bruker SHEXTL Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_structure_refinement
'XL Version 2008/4 (George M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_structure_solution
'XS Version 2008/1 (George M. Sheldrick, Acta Cryst. (2008). A64, 112-122) '
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            40491
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_correction_T_min  0.9663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS program multi-scan
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.611
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         5001
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.736
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0719P)^2^+1.3923P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1181
_reflns_number_gt                4772
_reflns_number_total             5001
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9qo00957d2.cif
_cod_data_source_block           opo1
_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/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/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 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/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 6909 2019-04-08 15:41:33Z antanas 

2022-11-30
Formula fixed to values more according to usual
chemical conventions and to be consistent with given Z.
                 miguel
;
_cod_original_formula_sum            'C100 H136 F12 N4 O5'
_cod_original_formula_moiety         '4(C23 H34 N O2) 4(C2 F3 O2), (H2 O)'
_cod_original_cell_volume        2439.76(16)
_cod_original_sg_symbol_H-M      C2
_cod_database_code               1555150