Synthesis of Benz-Fused Azoles via C-Heteroatom Coupling Reactions Catalyzed by Cu(I) in the Presence of Glycosyltriazole Ligands.
Mishra, Nidhi; Singh, Anoop S.; Agrahari, Anand K.; Singh, Sumit K.; Singh, Mala; Tiwari, Vinod K.; ACS combinatorial science 21 (2019) 389–399; doi:10.1021/acscombsci.9b00004

data_4514906
_publ_section_title
;
 Synthesis of Benz-Fused Azoles via C-Heteroatom Coupling Reactions
 Catalyzed by Cu(I) in the Presence of Glycosyltriazole Ligands.
;
_journal_issue                   5
_journal_name_full               'ACS combinatorial science'
_journal_page_first              389
_journal_page_last               399
_journal_paper_doi               10.1021/acscombsci.9b00004
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C13 H9 F N2'
_chemical_formula_sum            'C13 H9 F N2'
_chemical_formula_weight         212.22
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 90.000(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.608(3)
_cell_length_b                   7.1350(9)
_cell_length_c                   10.0478(11)
_cell_measurement_reflns_used    4234
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.60
_cell_measurement_theta_min      2.75
_cell_volume                     2122.6(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
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_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1131
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            30642
_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         28.285
_diffrn_reflns_theta_min         2.752
_diffrn_source                   x-ray
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       block
_exptl_crystal_F_000             880.0
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2646
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0540
_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^)+(0.0724P)^2^+0.7109P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1762
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1508
_reflns_number_total             2648
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            co9b00004_si_003.cif
_cod_data_source_block           shelx
_cod_database_code               4514906
_shelx_shelxl_version_number     2018/1
_shelx_res_checksum              74605
_shelx_hkl_checksum              21094