Domino 1,3-dipolar cycloaddition/ring-opening/ring-cleavage: synthesis of trisubstituted pyrrole and chiral dihydropyrrole-3-carbaldehydes
Pandidurai, Solai; Chinababu, Maddala; Sekar, Govindasamy; Chemical Communications 61 (2025) 5806–5809; doi:10.1039/D4CC06706A

data_7134331
_publ_section_title
;
 Domino 1,3-dipolar cycloaddition/ring-opening/ring-cleavage: synthesis of
 trisubstituted pyrrole and chiral dihydropyrrole-3-carbaldehydes
;
_journal_issue                   31
_journal_name_full               'Chemical Communications'
_journal_page_first              5806
_journal_page_last               5809
_journal_paper_doi               10.1039/D4CC06706A
_journal_volume                  61
_journal_year                    2025
_chemical_formula_sum            'C19 H12 F3 N O2'
_chemical_formula_weight         343.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2024-05-12 deposited with the CCDC.	2025-03-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.679(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.4749(4)
_cell_length_b                   9.2492(5)
_cell_length_c                   11.6066(8)
_cell_measurement_reflns_used    3556
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.39
_cell_measurement_theta_min      2.82
_cell_volume                     799.77(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5036
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.734
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_description       Block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
; 
 Flack x determined using 1085 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_coef       0.029(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2750
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0320
_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^)+(0.0339P)^2^+0.1728P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0792
_reflns_Friedel_coverage         0.839
_reflns_Friedel_fraction_full    0.959
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                2533
_reflns_number_total             2750
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc06706a2.cif
_cod_data_source_block           198
_cod_depositor_comments          'Adding full bibliography for 7134331.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7134331
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.986
_shelx_res_checksum              34769
_shelx_hkl_checksum              15970