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_4037268
_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_sum            'C15 H12 O6'
_chemical_formula_weight         288.25
_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   geom
_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                 96.543(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.9412(11)
_cell_length_b                   25.169(6)
_cell_length_c                   10.106(3)
_cell_measurement_reflns_used    6928
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.
_cell_measurement_theta_min      2.
_cell_volume                     1248.6(6)
_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  0.0298
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13785
_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         27.497
_diffrn_reflns_theta_min         1.618
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
'based on measured indexed crystal faces, Bruker SHELXTL2014 (Sheldrick, 2014)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.248
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.024
_exptl_transmission_factor_max   0.997
_exptl_transmission_factor_min   0.978
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2869
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0483P)^2^+0.5414P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0995
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2295
_reflns_number_total             2869
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01867_si_002.cif
_cod_data_source_block           BTP
_cod_original_cell_volume        1248.7(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4037268
_shelx_estimated_absorpt_t_min   0.971
_shelx_estimated_absorpt_t_max   0.997
_shelxl_version_number           2014/6
_shelx_res_checksum              58419
_shelx_hkl_checksum              79742