Cu/Pd-Catalyzed Synthesis of Fully Decorated Polycyclic Triazoles: Introducing C–H Functionalization to Multicomponent Multicatalytic Reactions ((MC)2R)
Qureshi, Zafar; Kim, Jung Yun; Bruun, Theodora; Lam, Heather; Lautens, Mark; ACS Catalysis 6 (2016) 4946–; doi:10.1021/acscatal.6b00858

data_4516694
_publ_section_title
;
 Cu/Pd-Catalyzed Synthesis of Fully Decorated Polycyclic Triazoles:
 Introducing C--H Functionalization to Multicomponent Multicatalytic
 Reactions ((MC)2R)
;
_journal_issue                   8
_journal_name_full               'ACS Catalysis'
_journal_page_first              4946
_journal_paper_doi               10.1021/acscatal.6b00858
_journal_volume                  6
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H25 N3 O2'
_chemical_formula_sum            'C24 H25 N3 O2'
_chemical_formula_weight         387.47
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.1839(2)
_cell_length_b                   17.3160(5)
_cell_length_c                   23.0197(7)
_cell_measurement_reflns_used    9120
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      67.03
_cell_measurement_theta_min      3.19
_cell_volume                     2066.35(12)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            32138
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.235
_diffrn_reflns_theta_max         67.235
_diffrn_reflns_theta_min         3.193
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_exptl_absorpt_coefficient_mu    0.639
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.6608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       needle
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
; 
 Flack x determined using 1418 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3655
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0296
_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^)+(0.0362P)^2^+0.4501P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0762
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                3525
_reflns_number_total             3655
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b00858_si_002.cif
_cod_data_source_block           d1619
_cod_database_code               4516694
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.872
_shelx_estimated_absorpt_t_max   0.963
_shelx_res_checksum              1455
_shelx_hkl_checksum              70595