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_7159842
_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         'C17 H11 Br N2 O'
_chemical_formula_sum            'C17 H11 Br N2 O'
_chemical_formula_weight         339.19
_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             2023-07-18
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-07-18 deposited with the CCDC.	2024-02-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.934(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.1247(5)
_cell_length_b                   13.5141(15)
_cell_length_c                   20.781(2)
_cell_measurement_reflns_used    3184
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.31
_cell_measurement_theta_min      2.48
_cell_volume                     1433.9(3)
_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  'XL  (Sheldrick, 2008)'
_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 0.988
_diffrn_measured_fraction_theta_max 0.968
_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  0.0547
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12448
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.335
_diffrn_reflns_theta_min         2.478
_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    2.866
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.3908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1126 before and 0.0685 after correction.
The Ratio of minimum to maximum transmission is 0.5241.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.258
_exptl_crystal_size_mid          0.231
_exptl_crystal_size_min          0.137
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.849
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3463
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0462P)^2^+0.8731P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1172
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2606
_reflns_number_total             3463
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00058g2.cif
_cod_data_source_block           agmk_591_0m
_cod_depositor_comments
'Adding full bibliography for 7159839--7159843.cif.'
_cod_original_cell_volume        1433.8(3)
_cod_database_code               7159842
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.695
_shelx_estimated_absorpt_t_min   0.525
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
1.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C8(H8), C5(H5), C6(H6), C17(H17), C16(H16), C14(H14), C15(H15)
1.c :
 C1(H1)
;
_shelx_res_checksum              17930
_olex2_submission_special_instructions 'No special instructions were received'