Catalytic Asymmetric [4+2] Cycloaddition of in Situ Generated o-Quinone Methide Imines with o-Hydroxystyrenes: Diastereo- and Enantioselective Construction of Tetrahydroquinoline Frameworks.
Li, Lin-Zhi; Wang, Cong-Shuai; Guo, Wei-Feng; Mei, Guang-Jian; Shi, Feng; The Journal of organic chemistry 83 (2018) 614–623; doi:10.1021/acs.joc.7b02533

data_4033347
_publ_section_title
;
 Catalytic Asymmetric [4+2] Cycloaddition of in Situ Generated o-Quinone
 Methide Imines with o-Hydroxystyrenes: Diastereo- and Enantioselective
 Construction of Tetrahydroquinoline Frameworks.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              614
_journal_page_last               623
_journal_paper_doi               10.1021/acs.joc.7b02533
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C28 H24 F N O'
_chemical_formula_sum            'C28 H24 F N O'
_chemical_formula_weight         409.48
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-06-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6532(3)
_cell_length_b                   21.5744(4)
_cell_length_c                   6.15200(10)
_cell_measurement_reflns_used    9980
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      70.123
_cell_measurement_theta_min      2.654
_cell_volume                     2210.31(7)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      301.02
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.973
_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  0.0348
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            16457
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.117
_diffrn_reflns_theta_min         7.677
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1461 before and 0.0644 after correction. The Ratio of minimum to maximum transmission is 0.6937. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.023
_refine_ls_abs_structure_details
;
 Flack x determined using 1544 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4100
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0530P)^2^+0.2659P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1088
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                3847
_reflns_number_total             4100
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02533_si_002.cif
_cod_data_source_block           cu_d8v17098_0m
_cod_depositor_comments          'Adding full bibliography for 4033347.cif.'
_cod_database_code               4033347
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.857
_shelx_estimated_absorpt_t_min   0.818
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C24(H24), C26(H26), C27(H27),
  C28(H28)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              95104
_shelx_hkl_checksum              48127
_olex2_submission_special_instructions 'No special instructions were received'