Four Mechanisms in the Reactions of 3-Aminopyrrole with 1,3,5-Triazines: Inverse Electron Demand Diels-Alder Cycloadditions vs SNAr Reactions via Uncatalyzed and Acid-Catalyzed Pathways
Michael De Rosa; David Arnold; Douglas Hartline; Journal of Organic Chemistry 78 (2013) 8614–8623; doi:10.1021/jo4012915

data_4028546
_publ_section_title
;
 Four Mechanisms in the Reactions of 3-Aminopyrrole with 1,3,5-Triazines:
 Inverse Electron Demand Diels-Alder Cycloadditions vs SNAr Reactions via
 Uncatalyzed and Acid-Catalyzed Pathways
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8614
_journal_page_last               8623
_journal_paper_doi               10.1021/jo4012915
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C10 H4 F4 N8'
_chemical_formula_sum            'C10 H4 F4 N8'
_chemical_formula_weight         312.21
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.571(7)
_cell_length_b                   20.299(11)
_cell_length_c                   4.706(3)
_cell_measurement_reflns_used    2156
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.597
_cell_measurement_theta_min      2.579
_cell_volume                     1200.9(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            7253
_diffrn_reflns_theta_full        28.16
_diffrn_reflns_theta_max         28.16
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2934
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0529P)^2^+0.0130P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.1006
_reflns_number_gt                2374
_reflns_number_total             2934
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4012915_si_003.cif
_cod_data_source_block           mxd9o
_cod_original_cell_volume        1200.8(12)
_cod_database_code               4028546