Synthesis of exo-Imidazolidin-2-one Dienes, Their Isomerization, and Selectivity in Diels-Alder Cycloadditions.
Espinoza-Hicks, Carlos; Montoya, Pablo; Bautista, Rafael; Jiménez-Vázquez, Hugo A; Rodríguez-Valdez, Luz M; Camacho-Dávila, Alejandro A; Cossío, Fernando P; Delgado, Francisco; Tamariz, Joaquín; The Journal of organic chemistry 83 (2018) 5347–5364; doi:10.1021/acs.joc.7b02344

data_4034805
_publ_section_title
;
 Synthesis of exo-Imidazolidin-2-one Dienes, Their Isomerization, and
 Selectivity in Diels-Alder Cycloadditions.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5347
_journal_page_last               5364
_journal_paper_doi               10.1021/acs.joc.7b02344
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C17 H14 N2 O'
_chemical_formula_sum            'C17 H14 N2 O'
_chemical_formula_weight         262.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-10-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.7477(13)
_cell_length_b                   7.4516(3)
_cell_length_c                   7.8082(4)
_cell_measurement_reflns_used    1935
_cell_measurement_temperature    292
_cell_measurement_theta_max      31.4060
_cell_measurement_theta_min      3.1340
_cell_volume                     1381.73(12)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      292
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_device_type  XcalSMo
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7092
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.581
_diffrn_reflns_theta_min         2.865
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.56
_exptl_crystal_size_min          0.54
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         2303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0577
_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^)+(0.0430P)^2^+0.3590P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1384
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1664
_reflns_number_total             2303
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02344_si_002.cif
_cod_data_source_block           0073-jt
_cod_original_cell_volume        1381.71(12)
_cod_database_code               4034805
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.955
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6'(H6'), C2'(H2'), C5'(H5'), C3'(H3'), C4'(H4')
;
_olex2_submission_special_instructions 'No special instructions were received'