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_7123118
_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         '2(C29 H22 N6 O6), C H2 Cl2'
_chemical_formula_sum            'C59 H46 Cl2 N12 O12'
_chemical_formula_weight         1185.98
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2019-02-18 deposited with the CCDC.    2019-03-05 downloaded from the CCDC.
;
_cell_angle_alpha                95.057(4)
_cell_angle_beta                 95.843(4)
_cell_angle_gamma                90.981(4)
_cell_formula_units_Z            2
_cell_length_a                   11.0997(8)
_cell_length_b                   11.2837(8)
_cell_length_c                   22.4561(16)
_cell_measurement_reflns_used    9901
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      63.9152
_cell_measurement_theta_min      3.9343
_cell_volume                     2786.1(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service vV6.2.9'
_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 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0625
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            37346
_diffrn_reflns_point_group_measured_fraction_full 0.914
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        64.172
_diffrn_reflns_theta_max         64.172
_diffrn_reflns_theta_min         3.934
_diffrn_source                   'I\mS  micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.690
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       prism
_exptl_crystal_F_000             1228
_exptl_crystal_size_max          0.391
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.118
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.693
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details
;
 Flack x determined using 5372 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1531
_refine_ls_number_reflns         16971
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0862
_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^)+(0.1693P)^2^+2.1102P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2326
_refine_ls_wR_factor_ref         0.2439
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_full    0.843
_reflns_Friedel_fraction_max     0.843
_reflns_number_gt                14507
_reflns_number_total             16971
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc06500d2.cif
_cod_data_source_block           fm56_vesely
_cod_database_code               7123118
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.558
_shelx_estimated_absorpt_t_max   0.826
_shelx_res_checksum              61210