BODIPY as electron withdrawing group for the activation of double bonds in asymmetric cycloaddition reactions
Guerrero-Corella, Andrea; Asenjo-Pascual, Juan; Pawar, Tushar Janardan; Díaz-Tendero, Sergio; Martín-Sómer, Ana; Gómez, Clarisa Villegas; Belmonte-Vázquez, José L.; Ramírez-Ornelas, Diana E.; Peña-Cabrera, Eduardo; Fraile, Alberto; Cruz, David Cruz; Alemán, José; Chemical Science  (2019) –; doi:10.1039/C9SC00959K

data_1550764
_publ_section_title
;
 BODIPY as electron withdrawing group for the activation of double bonds
 in asymmetric cycloaddition reactions
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC00959K
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C25.5 H25 B Br3 Cl F2 N2'
_chemical_formula_weight         683.46
_chemical_name_common            JA-58-cristal1
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_space_group_name_H-M_alt        'P 43 21 2'
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2018-11-20 deposited with the CCDC.    2019-03-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.0614(4)
_cell_length_b                   12.0614(4)
_cell_length_c                   37.3048(13)
_cell_measurement_reflns_used    9243
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      19.7756
_cell_measurement_theta_min      2.3524
_cell_volume                     5427.0(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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            92650
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    4.590
_exptl_absorpt_correction_T_max  0.49
_exptl_absorpt_correction_T_min  0.39
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'clear intense orange-red'
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             2696
_exptl_crystal_size_max          0.324
_exptl_crystal_size_mid          0.306
_exptl_crystal_size_min          0.182
_refine_diff_density_max         1.046
_refine_diff_density_min         -0.774
_refine_ls_abs_structure_details
;

Flack x determined using 1281 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         4987
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0606
_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^)+(0.0909P)^2^+9.9164P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1550
_refine_ls_wR_factor_ref         0.1720
_reflns_number_gt                3915
_reflns_number_total             4987
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc00959k2.cif
_cod_data_source_block           02446AndreaGuerrero
_cod_original_cell_volume        5427.0(4)
_cod_original_formula_sum        'C25.50 H25 B Br3 Cl F2 N2'
_cod_database_code               1550764
_shelx_res_checksum              84103