Catalytic Atroposelective Synthesis of N-Aryl Quinoid Compounds.
Vaidya, Sagar Dilip; Toenjes, Sean T.; Yamamoto, Nobuyuki; Maddox, Sean M.; Gustafson, Jeffrey L.; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.9b12994

data_4134055
_publ_section_title
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 Catalytic Atroposelective Synthesis of N-Aryl Quinoid Compounds.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b12994
_journal_year                    2020
_chemical_formula_moiety         'C H Cl3, C34 H31 N O4'
_chemical_formula_sum            'C35 H32 Cl3 N O4'
_chemical_formula_weight         636.96
_chemical_name_systematic
2-((5'-(tert-butyl)-4,4"-dimethoxy-[1,1':3',1"-terphenyl]-4'-yl)amino)naphthalene-1,4-dione
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2019-11-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.381(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8613(18)
_cell_length_b                   13.099(2)
_cell_length_c                   21.740(4)
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.40
_cell_measurement_theta_min      2.52
_cell_volume                     3051.6(9)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 MoK\a
_diffrn_detector_type            graphite
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0066
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            125568
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         2.454
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.342
_exptl_absorpt_correction_T_max  0.8750
_exptl_absorpt_correction_T_min  0.8011
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0556 before and 0.0295 after correction.
The Ratio of minimum to maximum transmission is 0.9155.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         6723
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0291
_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^)+(0.0413P)^2^+1.9174P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0798
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6403
_reflns_number_total             6723
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b12994_si_003.cif
_cod_data_source_block           sdv_02_105_0m
_cod_database_code               4134055
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.893
_shelx_estimated_absorpt_t_min   0.850
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C3(H3), C8(H8), C29(H29), C21(H21), C25(H25), C22(H22), C9(H9),
 C19(H19), C7(H7), C6(H6), C13(H13), C18(H18), C28(H28), C26(H26)
2.b Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C32(H32A,H32B,H32C), C23(H23A,H23B,
 H23C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              76813
_shelx_hkl_checksum              40257
_olex2_date_sample_completion    2019-08-09
_olex2_date_sample_data_collection 2019-08-07
_olex2_date_sample_submission    2019-08-07
_olex2_submission_special_instructions 'No special instructions were received'