N-Heterocyclic Imino Catalyzed 1,4-Regioselective Azide-Alkyne Cycloaddition (AAC): A Metal-free Approach
Revathi, Shanmugam; Lalasaheb, Aditya Shinde; Mulimani, Rajashekhar K.; Mandal, Debasish; Maity, Amit Ranjan; Garai, Somenath; Ghatak, Tapas; Chemical Communications  (2023) –; doi:10.1039/D3CC04065H

data_7132142
_publ_section_title
;
 N-Heterocyclic Imino Catalyzed 1,4-Regioselective Azide-Alkyne
 Cycloaddition (AAC): A Metal-free Approach
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04065H
_journal_year                    2023
_chemical_formula_moiety         'C25 H28 N4 O'
_chemical_formula_sum            'C25 H28 N4 O'
_chemical_formula_weight         400.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2023-07-02 deposited with the CCDC.	2023-09-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.917(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0389(17)
_cell_length_b                   31.902(7)
_cell_length_c                   9.109(2)
_cell_measurement_reflns_used    9998
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      21.69
_cell_measurement_theta_min      2.70
_cell_volume                     2196.3(8)
_computing_cell_refinement       'Bruker APEX4/SAINT'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
'Bruker D8 QUEST  diffractometer with PHOTON II detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            45071
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.019
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_min         2.699
_diffrn_source                   'i-mu-s microfocus source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.7033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3857
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0457
_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^)+(0.0470P)^2^+0.7257P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1192
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2814
_reflns_number_total             3857
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04065h3.cif
_cod_data_source_block           SRM54_0m_a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7132142
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.985
_shelx_estimated_absorpt_t_max   0.993
_shelx_res_checksum              93351
_shelx_hkl_checksum              76190