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_7248593
_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         'C36 H36 N3 O9'
_chemical_formula_sum            'C36 H36 N3 O9'
_chemical_formula_weight         654.68
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-02-10
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-02-10 deposited with the CCDC.	2024-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                97.433(5)
_cell_angle_beta                 91.503(4)
_cell_angle_gamma                92.772(4)
_cell_formula_units_Z            2
_cell_length_a                   6.0202(3)
_cell_length_b                   13.4077(7)
_cell_length_c                   19.4725(12)
_cell_measurement_reflns_used    4278
_cell_measurement_temperature    293.00(10)
_cell_measurement_theta_max      66.5710
_cell_measurement_theta_min      4.5500
_cell_volume                     1555.89(15)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f   -349.73  10.27   0.80   80.00 -97.45-107.50 -31.50    --   450
  2  \w    212.57 326.97   0.80   80.00    -- -107.50  89.85  47.34  143
  3  \w    212.57 326.97   0.80   80.00    -- -107.50  89.85-112.66  143
  4  \f    -10.27 349.73   0.80   56.00  37.96  48.14  31.50    --   450
  5  \w    212.57 326.97   0.80   80.00    -- -107.50  89.85 167.34  143
  6  \w     -7.25  87.95   0.80   56.00    --   48.14 -89.85  83.67  119
  7  \w    212.57 326.97   0.80   80.00    -- -107.50  89.85 -32.67  143
  8  \f    -10.27 349.73   0.80   80.00 -21.69-107.50  31.50    --   450
  9  \f   -339.92  20.08   0.80   64.00 -55.51 -77.50 -59.25    --   450
 10  \w    212.57 326.97   0.80   80.00    -- -107.50  89.85 -72.67  143
 11  \f   -339.92  20.08   0.80   80.00 -85.51-107.50 -59.25    --   450
 12  \w    212.57 326.97   0.80   80.00    -- -107.50  89.85 127.33  143
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1104
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            27348
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         3.329
_exptl_absorpt_coefficient_mu    0.837
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47188
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       needle
_exptl_crystal_F_000             690
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.624
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         5448
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1246
_refine_ls_R_factor_gt           0.0919
_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^)+(0.1682P)^2^+0.6499P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2498
_refine_ls_wR_factor_ref         0.2952
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3461
_reflns_number_total             5448
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc00818a2.cif
_cod_data_source_block           5b
_cod_depositor_comments
'Adding full bibliography for 7248591--7248593.cif.'
_cod_database_code               7248593
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.850
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O48B-C49B
 1.4 with sigma of 0.02
 C41B-C42A \\sim C41B-C42B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C49B) = Uanis(O48B) = Uanis(C45B) = Uanis(C44B) = Uanis(C43B) =
Uanis(C42B) = Uanis(C47B) = Uanis(C46B)
4. Others
 Fixed Sof: H41A(0.85) H41B(0.85) H41C(0.15) H41D(0.15) O48A(0.85) C42A(0.85)
 C43A(0.85) H43A(0.85) C49A(0.85) H49A(0.85) H49B(0.85) H49C(0.85) C45A(0.85)
 C44A(0.85) H44A(0.85) C46A(0.85) H46A(0.85) C47A(0.85) H47A(0.85) O48B(0.15)
 C43B(0.15) H43B(0.15) C44B(0.15) H44B(0.15) C45B(0.15) C46B(0.15) H46B(0.15)
 C47B(0.15) H47B(0.15) C42B(0.15) C49B(0.15) H49D(0.15) H49E(0.15) H49F(0.15)
5.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C22(H22A,H22B), C40(H40A,H40B), C24(H24A,H24B), C9(H9A,H9B),
 C41B(H41A,H41B), C41B(H41C,H41D)
5.b Aromatic/amide H refined with riding coordinates:
 C34(H34), C17(H17), C33(H33), C5(H5), C26(H26), C30(H30), C4(H4), C27(H27),
 C29(H29), C8(H8), C7(H7), C43A(H43A), C44A(H44A), C46A(H46A), C47A(H47A),
 C43B(H43B), C44B(H44B), C46B(H46B), C47B(H47B)
5.c Fitted hexagon refined as free rotating group:
 C43B(C44B,C45B,C46B,C47B,C42B)
5.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C32(H32A,H32B,H32C), C49A(H49A,H49B,H49C), C49B(H49D,H49E,
 H49F)
;
_shelx_res_checksum              80020
_shelx_hkl_checksum              2655
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;