Switching the Regioselectivity Access to Pyrroles and Isoquinolines from Ketoxime Acetates and Ynals
Liu, Tanggao; Xu, Fan; Liu, Xiaojuan; Huang, Zhiqing; Long, Lipeng; Xu, Guohai; Xiao, Hong; Chen, Zhengwang; ACS Omega  (2020) –; doi:10.1021/acsomega.0c05272

data_4518262
_publ_section_title
;
 Switching the Regioselectivity Access to Pyrroles and Isoquinolines from
 Ketoxime Acetates and Ynals
;
_journal_name_full               'ACS Omega'
_journal_paper_doi               10.1021/acsomega.0c05272
_journal_year                    2020
_chemical_formula_moiety         'C17 H13 N O'
_chemical_formula_sum            'C17 H13 N O'
_chemical_formula_weight         247.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-08-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                103.5340(10)
_cell_angle_beta                 93.3480(10)
_cell_angle_gamma                107.2230(10)
_cell_formula_units_Z            4
_cell_length_a                   9.6559(3)
_cell_length_b                   10.0445(3)
_cell_length_c                   14.3756(5)
_cell_measurement_reflns_used    9915
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.402
_cell_measurement_theta_min      2.953
_cell_volume                     1282.47(7)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18950
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         27.438
_diffrn_reflns_theta_min         2.953
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       strip
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5781
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0441
_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^)+(0.0402P)^2^+0.3990P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1138
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4614
_reflns_number_total             5781
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao0c05272_si_002.cif
_cod_data_source_block           cjl20200715pdsy1_0m
_cod_depositor_comments
;

2025-07-29
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C17 H13 N O)'
_cod_original_formula_sum        'C34 H26 N2 O2'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     494.57
_cod_database_code               4518262
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C26(H26), C18(H18), C20(H20), C31(H31), C34(H34), C33(H33), C22(H22),
 C30(H30), C32(H32), C27(H27), C19(H19), C21(H21), N1(H1), C2(H2A), C5(H5),
 C1(H1A), C15(H15), C13(H13), C17(H17), C4(H4), C10(H10), C16(H16), C9(H9),
 C3(H3), C14(H14)
;
_olex2_submission_special_instructions 'No special instructions were received'