Copper-catalyzed propargylic [3+3] cycloaddition with 1H-pyrazol-5(4H)-ones: enantioselective access to optically active dihydropyrano[2,3-c]pyrazoles.
Li, Ling; Liu, Zhen-Ting; Hu, Xiang-Ping; Chemical communications (Cambridge, England) 54 (2018) 12033–12036; doi:10.1039/c8cc05706k

data_7122398
_publ_section_title
;
 Copper-catalyzed propargylic [3+3] cycloaddition with
 1H-pyrazol-5(4H)-ones: enantioselective access to optically active
 dihydropyrano[2,3-c]pyrazoles.
;
_journal_issue                   85
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12033
_journal_page_last               12036
_journal_paper_doi               10.1039/c8cc05706k
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H17 Br N2 O'
_chemical_formula_weight         429.30
_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
;
2018-07-10 deposited with the CCDC.
2018-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.482(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.080(8)
_cell_length_b                   5.727(4)
_cell_length_c                   14.056(8)
_cell_measurement_reflns_used    1545
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      41.465
_cell_measurement_theta_min      5.483
_cell_volume                     965.7(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0804
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5535
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         1.580
_exptl_absorpt_coefficient_mu    2.145
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
; 
 Flack x determined using 968 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.010(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3466
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0441
_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=exp[1.0000(sin\q/\l)^2^)]/[\s^2^(Fo^2^)+(0.0354P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1083
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    0.938
_reflns_Friedel_fraction_max     0.936
_reflns_number_gt                2771
_reflns_number_total             3466
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc05706k2.cif
_cod_data_source_block           cd17259
_cod_depositor_comments          'Adding full bibliography for 7122398.cif.'
_cod_original_cell_volume        965.6(10)
_cod_database_code               7122398
_shelx_estimated_absorpt_t_min   0.674
_shelx_estimated_absorpt_t_max   0.882
_shelxl_version_number           2013-4
_shelx_res_checksum              40990