Diastereoselective synthesis of atropisomeric pyrazolyl pyrrolo[3,4-d]isoxazolidines via pyrazolyl nitrone cycloaddition to facially divergent maleimides: intensive NMR and DFT studies
Said, Awad I.; El-Emary, Talaat I.; RSC Advances 10 (2020) 845–850; doi:10.1039/C9RA10039C

data_7239877
_publ_section_title
;
 Diastereoselective synthesis of atropisomeric pyrazolyl
 pyrrolo[3,4-d]isoxazolidines via pyrazolyl nitrone cycloaddition to
 facially divergent maleimides: intensive NMR and DFT studies
;
_journal_issue                   2
_journal_name_full               'RSC Advances'
_journal_page_first              845
_journal_page_last               850
_journal_paper_doi               10.1039/C9RA10039C
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C22 H17 N3 O'
_chemical_formula_sum            'C22 H17 N3 O'
_chemical_formula_weight         339.38
_chemical_name_systematic
;
(NZ)-N-[(1,3-diphenyl-1<i>H</i>-pyrazol-4-yl)methylidene]-N-
oxidoanilinium
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc1z4qxr
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-02-03 deposited with the CCDC.	2019-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.060(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1084(8)
_cell_length_b                   10.8314(9)
_cell_length_c                   17.2226(14)
_cell_measurement_reflns_used    9914
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      74.6307
_cell_measurement_theta_min      4.8266
_cell_volume                     1694.9(2)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        '<i>SAINT</i>  (Bruker, 2016)'
_computing_molecular_graphics    '<i>DIAMOND</i> (Brandenburg & Putz, 2012)'
_computing_publication_material  '<i>SHELXTL</i> (Bruker, 2016)'
_computing_structure_refinement
'<i>SHELXL</i> 2016/6 (Sheldrick, 2015<i>b</i>)'
_computing_structure_solution    '<i>SHELXT</i> (Sheldrick, 2015<i>a</i>)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12691
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         74.622
_diffrn_reflns_theta_min         4.826
_diffrn_source                   'INCOATEC I\mS micro--focus source'
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '<i>SADABS</i> (Krause <i>et al.</i>, 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slab
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.242
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.098
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.781
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0046(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
'<i>SHELXL</i> 2016/6 (Sheldrick, 2015<i>b</i>)'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         3366
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0346
_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^)+(0.0366P)^2^+0.5699P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0864
_reflns_number_gt                3115
_reflns_number_total             3366
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra10039c2.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 7239877.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7239877
_publcif_datablock.id            {75547d80-8e1e-4857-9ce8-ee35942131ef}
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.856
_shelx_estimated_absorpt_t_max   0.938
_iucr_geom_hbonds_special_details
;
Cg2 and Cg3 are, respectively, the centroids of the C4--C9 
and C11--C16 benzene rings.
;
_shelx_res_checksum              36265