[3 + 2] Cycloaddition of α-Aryl-α-diazoacetates with Terminal Alkynes via the Cooperative Catalysis of Palladium and Acid
Guo, Hongyu; Zhang, Sheng; Yu, Xiaoqiang; Feng, Xiujuan; Yamamoto, Yoshinori; Bao, Ming; ACS Catalysis  (2021) 10789–10795; doi:10.1021/acscatal.1c02533

data_4518958
_publ_section_title
;
 [3 + 2] Cycloaddition of \a-Aryl-\a-diazoacetates with Terminal Alkynes
 via the Cooperative Catalysis of Palladium and Acid
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              10789
_journal_page_last               10795
_journal_paper_doi               10.1021/acscatal.1c02533
_journal_year                    2021
_chemical_formula_moiety         'C18 H13 F3 O2'
_chemical_formula_sum            'C18 H13 F3 O2'
_chemical_formula_weight         318.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-16
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_cell_angle_alpha                90
_cell_angle_beta                 101.044(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.918(4)
_cell_length_b                   5.5061(8)
_cell_length_c                   10.7277(15)
_cell_measurement_reflns_used    2447
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      23.892
_cell_measurement_theta_min      2.263
_cell_volume                     1502.6(4)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      120.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0746
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7052
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.738
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.0946 before and 0.0538 after correction. 
The Ratio of minimum to maximum transmission is 0.8923. 
The \l/2 correction factor is Not present. 
;
_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    1.407
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
; 
 Flack x determined using 662 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.5(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3238
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1083
_refine_ls_R_factor_gt           0.0597
_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^)+(0.0490P)^2^+0.9897P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1397
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_full    0.896
_reflns_Friedel_fraction_max     0.882
_reflns_number_gt                2153
_reflns_number_total             3238
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c02533_si_002.cif
_cod_data_source_block           zhl
_cod_original_cell_volume        1502.5(4)
_cod_database_code               4518958
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.977
_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: 
 C008(H008), C009(H009), C00B(H00B), C00E(H00E), C00G(H00G), C00H(H00H), 
 C00I(H00I), C00J(H00J), C00K(H00K), C00M(H00M) 
2.b Idealised Me refined as rotating group: 
 C00L(H00A,H00C,H00D) 
;
_shelx_res_checksum              58048
_shelx_hkl_checksum              15347
_olex2_submission_special_instructions 'No special instructions were received'