Diastereoselective synthesis of tetrahydropyrrolo[1,2-<i>d</i>]oxadiazoles from functionalized Δ<sup>1</sup>-pyrrolines and <i>in situ</i> generated nitrile oxides.
Ivanova, Evgeniya E.; Shabalin, Dmitrii A.; Ushakov, Igor' A.; Vashchenko, Alexander V.; Schmidt, Elena Yu; Trofimov, Boris A.; Organic & biomolecular chemistry 21 (2023) 1725–1736; doi:10.1039/d2ob02230c

data_7159097
_publ_section_title
;
 Diastereoselective synthesis of
 tetrahydropyrrolo[1,2-<i>d</i>]oxadiazoles from functionalized
 &#x394;<sup>1</sup>-pyrrolines and <i>in situ</i> generated nitrile
 oxides.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1725
_journal_page_last               1736
_journal_paper_doi               10.1039/d2ob02230c
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C19 H19 Cl N2 O2'
_chemical_formula_sum            'C19 H19 Cl N2 O2'
_chemical_formula_weight         342.81
_chemical_name_systematic
(5R,7aS)-3-(4-Chlorophenyl)-7,7-dimethyl-7a-phenyl-5,6,7,7a-tetrahydropyrrolo[1,2-d][1,2,4]oxadiazol-5-ol
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2021-01-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-11-21 deposited with the CCDC.	2023-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.84(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.286(6)
_cell_length_b                   21.161(16)
_cell_length_c                   18.146(13)
_cell_measurement_reflns_used    1577
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4
_cell_measurement_theta_min      2.4
_cell_volume                     3565(4)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_monochromator  No
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1269
_diffrn_reflns_av_unetI/netI     0.0595
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            72219
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.075
_diffrn_reflns_theta_min         2.228
_diffrn_source                   IuS
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1497 before and 0.0700 after correction.
The Ratio of minimum to maximum transmission is 0.8715.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       'colorless, prizm'
_exptl_crystal_F_000             1440
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
_exptl_crystal_size_max          0.394
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     444
_refine_ls_number_reflns         7036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1210
_refine_ls_R_factor_gt           0.0500
_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^+1.2825P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1172
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3969
_reflns_number_total             7036
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02230c2.cif
_cod_data_source_block           a_a
_cod_depositor_comments
;
          Adding full bibliography for 7159097.cif.

2024-10-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C38 H38 Cl2 N4 O4'
_cod_original_formula_weight         685.62
_cod_original_formula_moiety         '2(C19 H19 Cl N2 O2)'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        3566(4)
_cod_database_code               7159097
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.916
_olex2_refinement_description
;
1. 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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14), C36(H36)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C35(H35A,H35B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C8(H8), C9(H9), C10(H10), C16(H16), C17(H17), C18(H18),
 C19(H19), C21(H21), C22(H22), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31),
  C37(H37), C38(H38)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C15(H15A,H15B,H15C), C33(H33A,H33B,H33C), C34(H34A,H34B,
 H34C)
;
_shelx_res_checksum              71368
_olex2_submission_special_instructions 'No special instructions were received'
_publcif_funding_html
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;