Multicomponent Reaction through Cooperative Trio Catalysis Incorporating Enamine, Brønsted Acid and Metal Lewis Acid Catalysis: A Concise Route to Access Chromans
Karunaratne, Chamini; Sarkisian, Ryan G.; Reeves, Jennifer; Deng, Yongming; Wheeler, Kraig A.; Wang, Hong; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB00753A

data_7155571
_publ_section_title
;
 Multicomponent Reaction through Cooperative Trio Catalysis Incorporating
 Enamine, Br\/onsted Acid and Metal Lewis Acid Catalysis: A Concise Route
 to Access Chromans
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB00753A
_journal_year                    2017
_chemical_formula_moiety         'C20 H23 N O3'
_chemical_formula_sum            'C20 H23 N O3'
_chemical_formula_weight         325.39
_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   mixed
_audit_creation_method           SHELXL-2012
_audit_update_record
;
2016-11-21 deposited with the CCDC.
2017-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.443(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6820(6)
_cell_length_b                   7.2674(4)
_cell_length_c                   20.0741(10)
_cell_measurement_reflns_used    4019
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.899
_cell_measurement_theta_min      3.593
_cell_volume                     1657.55(15)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction
;
SAINT (Bruker, 2008) and XPREP (Bruker, 2008)
;
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10702
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.431
_diffrn_reflns_theta_min         4.021
_exptl_absorpt_coefficient_mu    0.699
_exptl_absorpt_correction_T_max  0.8299
_exptl_absorpt_correction_T_min  0.7490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2010)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       'transparent prism'
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2980
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0634
_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^)+(0.0597P)^2^+2.7815P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1481
_refine_ls_wR_factor_ref         0.1652
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2206
_reflns_number_total             2980
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00753a2.cif
_cod_data_source_block           hwang10
_cod_database_code               7155571
_shelxl_version_number           2012-9
_shelx_res_checksum              39244