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_7248591
_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         'C10 H12 N2 O4'
_chemical_formula_sum            'C10 H12 N2 O4'
_chemical_formula_weight         224.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-14
_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                 116.973(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.6549(3)
_cell_length_b                   12.8056(5)
_cell_length_c                   6.6575(3)
_cell_measurement_reflns_used    4910
_cell_measurement_temperature    200.00
_cell_measurement_theta_max      26.402
_cell_measurement_theta_min      3.182
_cell_volume                     505.64(4)
_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    'XS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      200.00
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 Venture, Photon II, Microfocus'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4910
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.402
_diffrn_reflns_theta_min         3.182
_exptl_absorpt_coefficient_mu    0.115
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_description       prism
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     75
_refine_ls_number_reflns         1022
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0403P)^2^+0.0972P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0868
_reflns_Friedel_coverage         0.000
_reflns_number_gt                988
_reflns_number_total             1022
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc00818a2.cif
_cod_data_source_block           3i
_cod_depositor_comments
'Adding full bibliography for 7248591--7248593.cif.'
_cod_database_code               7248591
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.670(2)
 0.330(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1)
3.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_shelx_res_checksum              48312
_shelx_hkl_checksum              27799
_olex2_submission_special_instructions 'No special instructions were received'