Organocatalytic Nonclassical Trienamine Activation in the Remote Alkylation of Furan Derivatives.
Skrzyńska, Anna; Przydacz, Artur; Albrecht, Łukasz; Organic letters 17 (2015) 5682–5685; doi:10.1021/acs.orglett.5b02979

data_1540596
_publ_section_title
;
 Organocatalytic Nonclassical Trienamine Activation in the Remote
 Alkylation of Furan Derivatives.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5682
_journal_page_last               5685
_journal_paper_doi               10.1021/acs.orglett.5b02979
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H16 Br N O4'
_chemical_formula_sum            'C20 H16 Br N O4'
_chemical_formula_weight         414.25
_chemical_name_systematic
(6R,7S)-5-(3-Nitro-1-(3-bromophenyl)2-phenylpropyl)-2-furfural
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1709(2)
_cell_length_b                   8.6771(2)
_cell_length_c                   25.4706(6)
_cell_measurement_temperature    100(2)
_cell_volume                     1805.86(7)
_computing_cell_refinement       'APEX2 (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'APEX2 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 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 Smart APEX2'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            14649
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.952
_diffrn_reflns_theta_min         3.470
_diffrn_source                   'microfocus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    3.322
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/4'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.015
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1401 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3429
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0206
_refine_ls_R_factor_gt           0.0201
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0323P)^2^+0.5950P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0532
_refine_ls_wR_factor_ref         0.0536
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3368
_reflns_number_total             3429
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b02979_si_002.cif
_cod_data_source_block           I
_cod_database_code               1540596
_shelx_shelxl_version_number     2014/7