Formal [3+2] cycloaddition of vinylcyclopropane azlactones to enals using synergistic catalysis
Kamlar, Martin; Franc, Michael; Cisarova, Ivana; Gyepes, Robert; Vesely, Jan; Chemical Communications  (2019) –; doi:10.1039/C8CC06500D

data_7123117
_publ_section_title
;
 Formal [3+2] cycloaddition of vinylcyclopropane azlactones to enals using
 synergistic catalysis
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC06500D
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesized by the authors'
_chemical_formula_moiety         'C22 H18 Br N O3'
_chemical_formula_sum            'C22 H18 Br N O3'
_chemical_formula_weight         424.28
_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-2018/1
_audit_update_record
;
2019-02-17 deposited with the CCDC.    2019-03-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.017(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.3124(6)
_cell_length_b                   6.3961(3)
_cell_length_c                   12.5551(6)
_cell_measurement_reflns_used    7483
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      63.9711
_cell_measurement_theta_min      3.5203
_cell_volume                     988.73(8)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service vV6.2.6'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Helios Cu  multilayer optic'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13789
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        65.606
_diffrn_reflns_theta_max         65.606
_diffrn_reflns_theta_min         3.520
_diffrn_source                   'I\mS  micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.009
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.363
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Flack x determined using 1094 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3381
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0602
_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^)+(0.0609P)^2^+1.4441P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1450
_refine_ls_wR_factor_ref         0.1528
_reflns_Friedel_coverage         0.817
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                2908
_reflns_number_total             3381
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc06500d2.cif
_cod_data_source_block           fm591_2_minor_vesely
_cod_database_code               7123117
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.408
_shelx_estimated_absorpt_t_max   0.910
_shelx_res_checksum              25311