Influence of Non-Covalent Interactions in the <i>Exo</i>- and Regioselectivity of Aza-Diels-Alder Reactions: Experimental and DFT Calculations.
Gallardo-Fuentes, Sebastián; Lezana, Nicolás; Lühr, Susan; Galdámez, Antonio; Vilches-Herrera, Marcelo; The Journal of organic chemistry 84 (2019) 10825–10831; doi:10.1021/acs.joc.9b01390

data_4033848
_publ_section_title
;
 Influence of Non-Covalent Interactions in the <i>Exo</i>- and
 Regioselectivity of Aza-Diels-Alder Reactions: Experimental and DFT
 Calculations.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10825
_journal_page_last               10831
_journal_paper_doi               10.1021/acs.joc.9b01390
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C27 H28 N4 O4'
_chemical_formula_sum            'C27 H28 N4 O4'
_chemical_formula_weight         472.53
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_audit_creation_date             2019-03-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_cell_angle_alpha                69.217(7)
_cell_angle_beta                 78.249(7)
_cell_angle_gamma                68.834(7)
_cell_formula_units_Z            2
_cell_length_a                   10.0551(18)
_cell_length_b                   10.1464(18)
_cell_length_c                   14.205(2)
_cell_measurement_reflns_used    6340
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.980
_cell_measurement_theta_min      2.180
_cell_volume                     1258.8(4)
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0974
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            36309
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.098
_diffrn_reflns_theta_max         25.098
_diffrn_reflns_theta_min         1.539
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.2755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1660 before and 0.0954 after correction.
The Ratio of minimum to maximum transmission is 0.3693.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       block
_exptl_crystal_F_000             500
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_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         4453
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0614
_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^)+(0.0836P)^2^+0.5756P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1616
_refine_ls_wR_factor_ref         0.1815
_reflns_number_gt                3228
_reflns_number_total             4453
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01390_si_003.cif
_cod_data_source_block           scd_291_0m
_cod_database_code               4033848
_shelx_shelxl_version_number     2016/6