Cascade Reaction of Morita-Baylis-Hillman Acetates with 1,1-Enediamines or Heterocyclic Ketene Aminals: Synthesis of Highly Functionalized 2-Aminopyrroles.
Liu, Jin; Li, Qi; Cao, Zheng-Mao; Jin, Yi; Lin, Jun; Yan, Sheng-Jiao; The Journal of organic chemistry 84 (2019) 1797–1807; doi:10.1021/acs.joc.8b02594

data_4033741
_publ_section_title
;
 Cascade Reaction of Morita-Baylis-Hillman Acetates with 1,1-Enediamines
 or Heterocyclic Ketene Aminals: Synthesis of Highly Functionalized
 2-Aminopyrroles.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1797
_journal_page_last               1807
_journal_paper_doi               10.1021/acs.joc.8b02594
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C20 H17 F2 N3 O4'
_chemical_formula_weight         401.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1649(13)
_cell_length_b                   10.6661(15)
_cell_length_c                   19.060(3)
_cell_measurement_reflns_used    1901
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.2808
_cell_measurement_theta_min      2.4659
_cell_volume                     1863.2(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.999
_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  0.0444
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10561
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.137
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.114
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.6(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3280
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0438P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0897
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2302
_reflns_number_total             3280
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02594_si_002.cif
_cod_data_source_block           1
_cod_database_code               4033741
_shelx_estimated_absorpt_t_min   0.960
_shelx_estimated_absorpt_t_max   0.972
_shelxl_version_number           2014-3
_shelx_res_checksum              70421
_shelx_hkl_checksum              61636