Synthesis of trifluoroethoxy/aryloxy cinnolines, cinnolinones and indazoles from <i>o</i>-alkynylanilines <i>via</i> metal-free diazotization reagent.
Kumar, Madan; Goswami, Avijit; Organic & biomolecular chemistry 22 (2024) 2608–2619; doi:10.1039/d4ob00058g

data_7159839
_publ_section_title
;
 Synthesis of trifluoroethoxy/aryloxy cinnolines, cinnolinones and
 indazoles from <i>o</i>-alkynylanilines <i>via</i> metal-free
 diazotization reagent.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2608
_journal_page_last               2619
_journal_paper_doi               10.1039/d4ob00058g
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C20 H13 Br N2 O'
_chemical_formula_sum            'C20 H13 Br N2 O'
_chemical_formula_weight         377.23
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-18
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-04-19 deposited with the CCDC.	2024-02-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.646(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1714(6)
_cell_length_b                   10.7451(6)
_cell_length_c                   15.1448(10)
_cell_measurement_reflns_used    3012
_cell_measurement_temperature    298
_cell_measurement_theta_max      25.28
_cell_measurement_theta_min      2.69
_cell_volume                     1654.53(17)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10102
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.407
_diffrn_reflns_theta_min         2.324
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.493
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1094 before and 0.0453 after correction.
The Ratio of minimum to maximum transmission is 0.7503.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3388
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0454
_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^)+(0.0367P)^2^+1.3965P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1126
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2256
_reflns_number_total             3388
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00058g2.cif
_cod_data_source_block           agmk_498a_0m
_cod_depositor_comments
'Adding full bibliography for 7159839--7159843.cif.'
_cod_database_code               7159839
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.873
_shelx_estimated_absorpt_t_min   0.592
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C20(H20), C16(H16), C2(H2), C17(H17), C10(H10), C5(H5), C12(H12),
 C19(H19), C3(H3), C11(H11), C18(H18), C4(H4)
;
_shelx_res_checksum              48990
_olex2_submission_special_instructions 'No special instructions were received'