Domino Acylation/Diels-Alder Synthesis of N-Alkyl-octahydroisoquinolin-1-one-8-carboxylic Acids under Low-Solvent Conditions.
Slauson, Stephen R.; Pemberton, Ryan; Ghosh, Partha; Tantillo, Dean J.; Aubé, Jeffrey; The Journal of organic chemistry 80 (2015) 5260–5271; doi:10.1021/acs.joc.5b00804

data_4031063
_publ_section_title
;
 Domino Acylation/Diels-Alder Synthesis of
 N-Alkyl-octahydroisoquinolin-1-one-8-carboxylic Acids under Low-Solvent
 Conditions.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5260
_journal_page_last               5271
_journal_paper_doi               10.1021/acs.joc.5b00804
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C23 H23 N O3'
_chemical_formula_weight         361.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 92.7960(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7262(2)
_cell_length_b                   17.1531(5)
_cell_length_c                   11.8482(3)
_cell_measurement_reflns_used    9932
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.85
_cell_measurement_theta_min      3.73
_cell_volume                     1771.34(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16750
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        66.000
_diffrn_reflns_theta_max         69.843
_diffrn_reflns_theta_min         4.539
_diffrn_source                   'Bruker MicroStar microfocus rotating anode'
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       Irregular
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0027(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         3155
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0313
_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^)+(0.0288P)^2^+0.7796P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0748
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3137
_reflns_number_total             3155
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00804_si_003.cif
_cod_data_source_block           q99c
_cod_database_code               4031063
_shelx_estimated_absorpt_t_min   0.853
_shelx_estimated_absorpt_t_max   0.925
_shelxl_version_number           2013-4
_shelx_res_checksum              96730
_shelx_hkl_checksum              41748