Total Syntheses of Aporphine Alkaloids via Benzyne Chemistry: An Approach to the Formation of Aporphine Cores.
Rossini, Allan F. C.; Muraca, Ana Carolina A.; Casagrande, Gleison A.; Raminelli, Cristiano; The Journal of organic chemistry 80 (2015) 10033–10040; doi:10.1021/acs.joc.5b01634

data_4031532
_publ_section_title
;
 Total Syntheses of Aporphine Alkaloids via Benzyne Chemistry: An Approach
 to the Formation of Aporphine Cores.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10033
_journal_page_last               10040
_journal_paper_doi               10.1021/acs.joc.5b01634
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C21 H20 F3 N O4'
_chemical_formula_sum            'C21 H20 F3 N O4'
_chemical_formula_weight         407.38
_chemical_name_common            'Trifluormethilamide like-cumeno system'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2014-12-05T10:52:14-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                102.743(2)
_cell_angle_beta                 93.346(2)
_cell_angle_gamma                96.979(2)
_cell_formula_units_Z            2
_cell_length_a                   8.5712(7)
_cell_length_b                   9.4277(8)
_cell_length_c                   11.6959(9)
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      133.439
_cell_measurement_theta_min      10.439
_cell_volume                     911.45(13)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'ORTEP 3'
_computing_publication_material  WINGX
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.019
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24395
_diffrn_reflns_theta_full        66.71
_diffrn_reflns_theta_max         66.71
_diffrn_reflns_theta_min         5.22
_exptl_absorpt_coefficient_mu    1.05
_exptl_absorpt_correction_T_max  0.8584
_exptl_absorpt_correction_T_min  0.7576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        SADABS-2014/2 (Bruker,2014) was used for absorption correction.
        wR2(int) was 0.0536 before and 0.0350 after correction.
        The Ratio of minimum to maximum transmission is 0.8069.
        The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.735
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.08
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.08
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0585P)^2^+0.7909P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1168
_reflns_number_gt                3100
_reflns_number_total             3138
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo5b01634_si_002.cif
_cod_data_source_block           p-1
_cod_depositor_comments          'Adding full bibliography for 4031532.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4031532