Controllable synthesis of 3-iodo-2H-quinolizin-2-ones and 1,3-diiodo-2H-quinolizin-2-ones via electrophilic cyclization of azacyclic ynones
Wang, Yan-Bo; Yang, Wan-Wan; Zhang, Jing-Wen; Chen, Lu-Lu; Fu, Ji-Ya; Zhu, Jun-Yan; Chemical Communications  (2019) –; doi:10.1039/C9CC06250E

data_7124176
_publ_section_title
;
 Controllable synthesis of 3-iodo-2H-quinolizin-2-ones and
 1,3-diiodo-2H-quinolizin-2-ones via electrophilic cyclization of
 azacyclic ynones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC06250E
_journal_year                    2019
_chemical_formula_moiety         'C15 H9 I2 N O'
_chemical_formula_sum            'C15 H9 I2 N O'
_chemical_formula_weight         473.03
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-16 deposited with the CCDC.    2019-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.219(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9008(15)
_cell_length_b                   17.581(3)
_cell_length_c                   9.4398(16)
_cell_measurement_reflns_used    4702
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.32
_cell_volume                     1449.0(4)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8190
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.317
_exptl_absorpt_coefficient_mu    4.331
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1120 before and 0.0372 after correction. The Ratio of minimum to maximum transmission is 0.6806. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    2.168
_exptl_crystal_description       prism
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.961
_refine_diff_density_min         -0.802
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2949
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0233
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0216P)^2^+1.2262P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0531
_refine_ls_wR_factor_ref         0.0554
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2573
_reflns_number_total             2949
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc06250e2.cif
_cod_data_source_block           a_CCDC1
_cod_database_code               7124176
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.624
_shelx_estimated_absorpt_t_min   0.263
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15)
;
_olex2_submission_special_instructions 'No special instructions were received'