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_4036454
_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            'C10 H14 Br2 O3'
_chemical_formula_weight         342.03
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 111.066(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1597(12)
_cell_length_b                   24.878(5)
_cell_length_c                   7.5576(15)
_cell_measurement_reflns_used    1907
_cell_measurement_temperature    130.0(2)
_cell_measurement_theta_max      27.22
_cell_measurement_theta_min      3.28
_cell_volume                     1080.7(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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0307
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5580
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.637
_exptl_absorpt_coefficient_mu    7.484
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.102
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.681
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         1899
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0300
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0402P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0726
_refine_ls_wR_factor_ref         0.0747
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1655
_reflns_number_total             1899
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02037_si_002.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4036454
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              65905
_shelx_hkl_checksum              2839