Copper-catalyzed cross-coupling and sequential allene-mediated cyclization for the synthesis of 1,2,3-triazolo[1,5-<i>a</i>]quinolines.
Yang, Jianhua; Xiong, Shaoqi; Ren, Yongsheng; Xiao, Tiebo; Jiang, Yubo; Organic & biomolecular chemistry 18 (2020) 7174–7182; doi:10.1039/d0ob00435a

data_7157685
_publ_section_title
;
 Copper-catalyzed cross-coupling and sequential allene-mediated
 cyclization for the synthesis of 1,2,3-triazolo[1,5-<i>a</i>]quinolines.
;
_journal_issue                   36
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7174
_journal_page_last               7182
_journal_paper_doi               10.1039/d0ob00435a
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C24 H19 N3'
_chemical_formula_sum            'C24 H19 N3'
_chemical_formula_weight         349.42
_chemical_name_systematic
4-benzyl-3-(p-tolyl)-[1,2,3]triazolo[1,5-a]quinoline
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc249jss
_audit_creation_date             2019-12-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-25 deposited with the CCDC.	2020-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.571(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.4957(13)
_cell_length_b                   7.8032(5)
_cell_length_c                   25.760(2)
_cell_measurement_reflns_used    3304
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.6830
_cell_measurement_theta_min      2.9340
_cell_volume                     3714.1(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -26.60   0.00   0.70    7.50    --  -16.28 -57.00-120.00   38
  2  \w    -88.00   2.30   0.70    7.50    --  -16.28 -19.00 -30.00  129
  3  \w    -12.00  20.90   0.70    7.50    --  -16.28 -99.00  90.00   47
  4  \w    -10.00  48.10   0.70    7.50    --  -16.28  38.00 120.00   83
  5  \w     38.00  87.00   0.70    7.50    --   15.65 178.00 -90.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0337688000
_diffrn_orient_matrix_UB_12      -0.0331279000
_diffrn_orient_matrix_UB_13      0.0095206000
_diffrn_orient_matrix_UB_21      -0.0110483000
_diffrn_orient_matrix_UB_22      0.0095757000
_diffrn_orient_matrix_UB_23      0.0258629000
_diffrn_orient_matrix_UB_31      -0.0145703000
_diffrn_orient_matrix_UB_32      -0.0840386000
_diffrn_orient_matrix_UB_33      -0.0008132000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0717
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            19282
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         2.656
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.250
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         7966
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1387
_refine_ls_R_factor_gt           0.0668
_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^)+(0.0645P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1772
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3860
_reflns_number_total             7966
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00435a2.cif
_cod_data_source_block           exp_7760
_cod_depositor_comments          'Adding full bibliography for 7157685.cif.'
_cod_original_cell_volume        3714.0(5)
_cod_database_code               7157685
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.978
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18a,H18b), C42(H42a,H42b)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C7(H7), C16(H16), C2(H2), C20(H20), C40(H40), C31(H31), C36(H36),
 C15(H15), C13(H13), C37(H37), C39(H39), C3(H3), C5(H5), C24(H24), C44(H44),
 C4(H4), C48(H48), C21(H21), C29(H29), C26(H26), C22(H22), C23(H23), C45(H45),
 C28(H28), C27(H27), C47(H47), C46(H46)
2.c Idealised Me refined as rotating group:
 C17(H17a,H17b,H17c), C41(H41a,H41b,H41c)
;
_olex2_date_sample_data_collection 2019-12-13
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.182
_oxdiff_exptl_absorpt_empirical_full_min 0.481