Stereoselective synthesis of pyrano[2,3-<i>c</i>]pyrazolone derivatives <i>via</i> light-induced NHC catalyzed [4 + 2] annulations.
Miao, Siyan; Li, Xian; Chen, Yao; Yu, Chenxia; Wang, Jiaomei; Yao, Changsheng; Zhang, Kai; Organic & biomolecular chemistry 23 (2025) 6644–6651; doi:10.1039/d5ob00586h

data_7160607
_publ_section_title
;
 Stereoselective synthesis of pyrano[2,3-<i>c</i>]pyrazolone derivatives
 <i>via</i> light-induced NHC catalyzed [4 + 2] annulations.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6644
_journal_page_last               6651
_journal_paper_doi               10.1039/d5ob00586h
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H21 Br N2 O2'
_chemical_formula_sum            'C26 H21 Br N2 O2'
_chemical_formula_weight         473.36
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-06-20
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_audit_update_record
;
2025-06-20 deposited with the CCDC.	2025-06-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.044(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.932(4)
_cell_length_b                   14.231(7)
_cell_length_c                   9.581(5)
_cell_measurement_reflns_used    4140
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.728
_cell_measurement_theta_min      2.538
_cell_volume                     1094.2(9)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7906
_diffrn_reflns_point_group_measured_fraction_full 0.829
_diffrn_reflns_point_group_measured_fraction_max 0.801
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.986
_diffrn_reflns_theta_min         2.366
_exptl_absorpt_coefficient_mu    1.904
_exptl_absorpt_correction_type   none
_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    1.437
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.757
_refine_diff_density_min         -0.656
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1156 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.045(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4217
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0354
_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^)+(0.0267P)^2^+0.3514P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.0902
_reflns_Friedel_coverage         0.575
_reflns_Friedel_fraction_full    0.651
_reflns_Friedel_fraction_max     0.609
_reflns_number_gt                3647
_reflns_number_total             4217
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00586h2.cif
_cod_data_source_block           3a
_cod_depositor_comments          'Adding full bibliography for 7160607.cif.'
_cod_database_code               7160607
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C14(H14)
1.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C26(H26)
1.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C7(H7A,H7B,H7C)
;
_shelx_res_checksum              97291
_olex2_submission_special_instructions 'No special instructions were received'