Cu-catalysed direct C-H (hetero)arylation of [1,2,4]triazolo[4,3-a]pyridine to construct deep-blue-emitting luminophores.
Wu, Jie; You, Qiulin; Lan, Jingbo; Guo, Qiang; Li, Xiaoyu; Xue, Ying; You, Jingsong; Organic & biomolecular chemistry 13 (2015) 5372–5375; doi:10.1039/c5ob00552c

data_7154416
_publ_section_title
;
 Cu-catalysed direct C-H (hetero)arylation of
 [1,2,4]triazolo[4,3-a]pyridine to construct deep-blue-emitting
 luminophores.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5372
_journal_page_last               5375
_journal_paper_doi               10.1039/c5ob00552c
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C12 H9 N3'
_chemical_formula_sum            'C12 H9 N3'
_chemical_formula_weight         195.22
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-11-05
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2014-11-05 deposited with the CCDC.
2015-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2050(5)
_cell_length_b                   10.6112(6)
_cell_length_c                   10.8283(6)
_cell_measurement_reflns_used    1270
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      72.3820
_cell_measurement_theta_min      7.9570
_cell_volume                     942.76(9)
_computing_cell_refinement
'CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48)'
_computing_data_collection
'CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48)'
_computing_data_reduction
'CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -77.0000 -150.0000 94

  2 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000   90.0000 74

  3 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000  -60.0000 84

  4 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000   30.0000 84

  5 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -38.0000 -150.0000 88

  6 omega   70.00  178.00   1.0000    6.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -120.0000 108

  7 omega   38.00   91.00   1.0000    6.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

  8 omega   48.00  105.00   1.0000    6.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 57

  9 omega   48.00   78.00   1.0000    6.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 30

 10 omega   75.00  133.00   1.0000    6.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   30.0000 58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1876144000
_diffrn_orient_matrix_UB_12      -0.0059976000
_diffrn_orient_matrix_UB_13      0.0026478000
_diffrn_orient_matrix_UB_21      0.0079415000
_diffrn_orient_matrix_UB_22      0.1449019000
_diffrn_orient_matrix_UB_23      0.0036777000
_diffrn_orient_matrix_UB_31      -0.0036998000
_diffrn_orient_matrix_UB_32      -0.0036993000
_diffrn_orient_matrix_UB_33      0.1422615000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2725
_diffrn_reflns_point_group_measured_fraction_full 0.738
_diffrn_reflns_point_group_measured_fraction_max 0.748
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.978
_diffrn_reflns_theta_min         6.821
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71219
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 337 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1259
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0456
_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^)+(0.0820P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1197
_reflns_Friedel_coverage         0.411
_reflns_Friedel_fraction_full    0.458
_reflns_Friedel_fraction_max     0.465
_reflns_number_gt                1205
_reflns_number_total             1259
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob00552c2.cif
_cod_data_source_block           wj002
_cod_depositor_comments          'Adding full bibliography for 7154416.cif.'
_cod_original_cell_volume        942.77(10)
_cod_database_code               7154416
_shelxl_version_number           2014-1
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12)
;
_shelx_res_checksum              87577
_olex2_submission_special_instructions 'No special instructions were received'