Copper-catalyzed enantioselective alkynylation of pyrazole-4,5-diones with terminal alkynes
Lu, Jian; Luo, Ling-Shan; Sha, Feng; Li, Qiong; Wu, Xin-Yan; Chemical Communications  (2019) –; doi:10.1039/C9CC05252F

data_7124095
_publ_section_title
;
 Copper-catalyzed enantioselective alkynylation of pyrazole-4,5-diones
 with terminal alkynes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC05252F
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H16 N2 O3'
_chemical_formula_weight         320.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2019-03-28 deposited with the CCDC.    2019-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.4420(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.2047(2)
_cell_length_b                   4.92460(10)
_cell_length_c                   14.6571(3)
_cell_measurement_reflns_used    9930
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      140.213
_cell_measurement_theta_min      11.671
_cell_volume                     825.46(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12251
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.485
_diffrn_reflns_theta_min         9.573
_exptl_absorpt_coefficient_mu    0.721
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details
; 
 Flack x determined using 1203 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.03(7)
_refine_ls_extinction_coef       0.059(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2826
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0312
_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^)+(0.0549P)^2^+0.0445P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0865
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_full    0.945
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                2789
_reflns_number_total             2826
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc05252f2.cif
_cod_data_source_block           cu_d8v19258_0m
_cod_database_code               7124095
_shelx_estimated_absorpt_t_min   0.869
_shelx_estimated_absorpt_t_max   0.918
_shelxl_version_number           2013-4
_shelx_res_checksum              60973