Selective and Sequential Aminolysis of Benzotrifuranone: Synergism of Electronic Effects and Ring Strain Gradient.
Baker, Matthew B.; Ferreira, Renan B.; Tasseroul, Jonathan; Lampkins, Andrew J.; Al Abbas, Alexandre; Abboud, Khalil A.; Castellano, Ronald K.; The Journal of organic chemistry 81 (2016) 9279–9288; doi:10.1021/acs.joc.6b01867

data_4037270
_publ_section_title
;
 Selective and Sequential Aminolysis of Benzotrifuranone: Synergism of
 Electronic Effects and Ring Strain Gradient.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9279
_journal_page_last               9288
_journal_paper_doi               10.1021/acs.joc.6b01867
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C17 H13 N O7, 0.5(C6 H6)'
_chemical_formula_sum            'C20 H16 N O7'
_chemical_formula_weight         382.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2016-06-30 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 100.698(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.2630(7)
_cell_length_b                   4.8365(2)
_cell_length_c                   19.3532(7)
_cell_measurement_reflns_used    9826
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.
_cell_measurement_theta_min      2.
_cell_volume                     1679.74(11)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2008)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2008)'
_computing_data_reduction        'Bruker Apex2 SAINT (Bruker, 2008)'
_computing_molecular_graphics    'XP in SHELXTL-plus, Bruker 2014'
_computing_publication_material  'SHELXL2014/7, Sheldrick, G. M. 2014'
_computing_structure_refinement  'SHELXL2014/7, Sheldrick G. M. 2014'
_computing_structure_solution    'SHELXL2014/7, Sheldrick G. M. 2014'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16071
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         1.699
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.9956
_exptl_absorpt_correction_T_min  0.9820
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
'based on measured indexed crystal faces, Bruker SHELXTL2014 (Sheldrick, 2014)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_description       needle
_exptl_crystal_F_000             796
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3866
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0829P)^2^+0.4568P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1367
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3028
_reflns_number_total             3866
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01867_si_002.cif
_cod_data_source_block           1c
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4037270
_shelx_estimated_absorpt_t_min   0.968
_shelx_estimated_absorpt_t_max   0.996
_shelxl_version_number           2014/6
_shelx_res_checksum              6853
_shelx_hkl_checksum              1688