A transition-metal-free azide–alkyne cycloaddition/hydroamination cascade reaction for the construction of triazole-fused piperazin-2-ones
Qiu, Kongxi; Wu, Kaifu; Ma, Haowen; Ao, Yunlin; Zhou, Wei; Cai, Qian; Organic & Biomolecular Chemistry 22 (2024) 1176–1180; doi:10.1039/D3OB01999C

data_7159748
_publ_section_title
;
 A transition-metal-free azide--alkyne cycloaddition/hydroamination
 cascade reaction for the construction of triazole-fused piperazin-2-ones
;
_journal_issue                   6
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              1176
_journal_page_last               1180
_journal_paper_doi               10.1039/D3OB01999C
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C18 H14 N4 O'
_chemical_formula_sum            'C18 H14 N4 O'
_chemical_formula_weight         302.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-21
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-10-06 deposited with the CCDC.	2024-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.52660(10)
_cell_length_b                   12.2496(3)
_cell_length_c                   21.7057(5)
_cell_measurement_reflns_used    3490
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.6500
_cell_measurement_theta_min      4.0620
_cell_volume                     1469.45(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_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    -69.00  32.00   1.00    1.00    --  -40.73  57.00-180.00  101
  2  \w     29.00  55.00   1.00    1.00    --   40.73-125.00  90.00   26
  3  \w     24.00  82.00   1.00    1.00    --   40.73 -99.00-120.00   58
  4  \w     58.00  95.00   1.00    1.00    --   40.73-125.00 150.00   37
  5  \w     35.00 133.00   1.00    2.05    --  107.58 -45.00 -90.00   98
  6  \w    119.00 149.00   1.00    2.05    --  107.58  88.00  71.00   30
  7  \w     83.00 163.00   1.00    2.05    --  107.58  45.00-150.00   80
  8  \w    153.00 178.00   1.00    2.05    --  107.58  15.00 150.00   25
  9  \w     55.00 126.00   1.00    2.05    --  107.58  15.00-180.00   71
 10  \w    130.00 162.00   1.00    2.05    --  107.58  15.00-180.00   32
 11  \w     55.00  87.00   1.00    2.05    --  107.58  15.00 150.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1321779000
_diffrn_orient_matrix_UB_12      -0.1105018000
_diffrn_orient_matrix_UB_13      -0.0043440000
_diffrn_orient_matrix_UB_21      -0.1342289000
_diffrn_orient_matrix_UB_22      -0.0252792000
_diffrn_orient_matrix_UB_23      -0.0605281000
_diffrn_orient_matrix_UB_31      0.2052930000
_diffrn_orient_matrix_UB_32      0.0546125000
_diffrn_orient_matrix_UB_33      -0.0368045000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5181
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.772
_diffrn_reflns_theta_min         4.073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.714
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1057 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.26(19)
_refine_ls_extinction_coef       0.0057(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2873
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0318
_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^)+(0.0448P)^2^+0.0738P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0828
_reflns_Friedel_coverage         0.669
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.943
_reflns_number_gt                2712
_reflns_number_total             2873
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01999c2.cif
_cod_data_source_block           qkx-1020
_cod_depositor_comments          'Adding full bibliography for 7159748.cif.'
_cod_database_code               7159748
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.932
_shelx_estimated_absorpt_t_min   0.907
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_res_checksum              20196
_olex2_date_sample_data_collection 2022-10-20
_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 1.472
_oxdiff_exptl_absorpt_empirical_full_min 0.470