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_4514908
_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_sum            'C13 H9 N3 O2 S'
_chemical_formula_weight         271.29
_space_group_crystal_system      monoclinic
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_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
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_atom_sites_solution_hydrogens   geom
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_cell_angle_gamma                90
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_cell_length_c                   25.427(15)
_cell_measurement_reflns_used    6010
_cell_measurement_temperature    296(2)
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_cell_measurement_theta_min      3.14
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_computing_cell_refinement       'Bruker SAINT'
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_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 0.980
_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  0.0752
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
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_diffrn_reflns_limit_l_min       -33
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_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.980
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_diffrn_reflns_theta_max         28.558
_diffrn_reflns_theta_min         3.142
_diffrn_source                   x-ray
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_description       block
_exptl_crystal_F_000             800
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_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.37
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_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         6047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0564
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0888P)^2^+0.2738P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1733
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3807
_reflns_number_total             6047
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            co9b00004_si_002.cif
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_cod_database_code               4514908
_shelx_shelxl_version_number     2018/1
_shelx_res_checksum              50609
_shelx_hkl_checksum              89522