Medium-Ring Effects on the Endo/Exo Selectivity of the Organocatalytic Intramolecular Diels-Alder Reaction.
Hooper, Joel F.; James, Natalie C.; Bozkurt, Esra; Aviyente, Viktorya; White, Jonathan M.; Holland, Mareike C.; Gilmour, Ryan; Holmes, Andrew B.; Houk, K. N.; The Journal of organic chemistry 80 (2015) 12058–12075; doi:10.1021/acs.joc.5b02037

data_4036453
_publ_section_title
;
 Medium-Ring Effects on the Endo/Exo Selectivity of the Organocatalytic
 Intramolecular Diels-Alder Reaction.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12058
_journal_page_last               12075
_journal_paper_doi               10.1021/acs.joc.5b02037
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C20 H22 N4 O5'
_chemical_formula_weight         398.41
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_space_group_name_H-M_alt        'P 43 21 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.7298(4)
_cell_length_b                   10.7298(4)
_cell_length_c                   35.040(3)
_cell_measurement_reflns_used    2338
_cell_measurement_temperature    130.0(2)
_cell_measurement_theta_max      19.34
_cell_measurement_theta_min      2.23
_cell_volume                     4034.1(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      130.0(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Apex CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_av_unetI/netI     0.0737
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            21393
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.983
_diffrn_reflns_theta_max         24.983
_diffrn_reflns_theta_min         1.985
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       prism
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 737 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.0(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.888
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3556
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.888
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0444
_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^)+(0.0352P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0891
_reflns_Friedel_coverage         0.657
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2465
_reflns_number_total             3556
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02037_si_003.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        4034.2(4)
_cod_database_code               4036453
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              44223
_shelx_hkl_checksum              2879