Zinc(ii)-catalysed cyclocondensation of oxime ethers triggered by polarity inversion: construction of fused pyrroles
Takeda, Norihiko; Fujita, Sora; Murakami, Kaho; Honda, Chihiro; Tomoda, Hina; Yasui, Motohiro; Yamada, Takahiro; Ueda, Masafumi; Chemical Communications 61 (2025) 7995–7998; doi:10.1039/D5CC01362C

data_7134446
_publ_section_title
;
 Zinc(ii)-catalysed cyclocondensation of oxime ethers triggered by
 polarity inversion: construction of fused pyrroles
;
_journal_issue                   44
_journal_name_full               'Chemical Communications'
_journal_page_first              7995
_journal_page_last               7998
_journal_paper_doi               10.1039/D5CC01362C
_journal_volume                  61
_journal_year                    2025
_chemical_formula_sum            'C24 H22 Br N O'
_chemical_formula_weight         420.33
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2025-02-12 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.893(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.5551(4)
_cell_length_b                   6.0134(3)
_cell_length_c                   19.1446(8)
_cell_measurement_temperature    293(2)
_cell_volume                     981.31(8)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            19448
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.993
_diffrn_reflns_theta_min         2.135
_exptl_absorpt_coefficient_mu    2.108
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_F_000             432
_refine_diff_density_max         0.991
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 1566 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4719
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0332P)^2^+0.5228P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0801
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                4124
_reflns_number_total             4719
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc01362c2.cif
_cod_data_source_block           takeda_autored_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7134445--7134446.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7134446
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              4051
_shelx_hkl_checksum              68197