Sequential Glaser reaction – diastereoselective cyclocarboxylation of propargylamines with CO2: a green catalytic access to bis-oxazolidinonedienes and their topochemical polymerization
Mele, Francesco; Constantin, Ana Maria; Sacchelli, Filippo; Schiroli, Debora; Mazzeo, Paolo Pio; Maestri, Giovanni; Motti, Elena; Maggi, Raimondo; Mancuso, Raffaella; Gabriele, Bartolo; Pancrazzi, Francesco; Della Ca’, Nicola; Green Chemistry 26 (2024) 6429–6435; doi:10.1039/D4GC00818A

data_7248592
_publ_section_title
;
 Sequential Glaser reaction -- diastereoselective cyclocarboxylation of
 propargylamines with CO2: a green catalytic access to
 bis-oxazolidinonedienes and their topochemical polymerization
;
_journal_issue                   11
_journal_name_full               'Green Chemistry'
_journal_page_first              6429
_journal_page_last               6435
_journal_paper_doi               10.1039/D4GC00818A
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C24 H24 N2 O6'
_chemical_formula_sum            'C24 H24 N2 O6'
_chemical_formula_weight         436.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-24
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-12-24 deposited with the CCDC.	2024-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.2560(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   40.9802(7)
_cell_length_b                   5.98560(10)
_cell_length_c                   8.7293(2)
_cell_measurement_reflns_used    7591
_cell_measurement_temperature    200.00
_cell_measurement_theta_max      72.046
_cell_measurement_theta_min      2.174
_cell_volume                     2124.07(7)
_computing_cell_refinement       SHELXT
_computing_data_reduction        SHELXT
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      200.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13280
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.042
_diffrn_reflns_theta_min         2.174
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.818
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1194 before and 0.0517 after correction.
The Ratio of minimum to maximum transmission is 0.7793.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       needle
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0343
_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^)+(0.0489P)^2^+0.9281P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0901
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1872
_reflns_number_total             2013
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc00818a2.cif
_cod_data_source_block           3b
_cod_depositor_comments
'Adding full bibliography for 7248591--7248593.cif.'
_cod_database_code               7248592
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
;
_shelx_res_checksum              65588
_shelx_hkl_checksum              34324
_olex2_exptl_crystal_mounting_method CryoLoop
_olex2_submission_special_instructions 'No special instructions were received'