Chiral Brønsted Acid Catalyzed Enantioselective Dehydrative Nazarov-Type Electrocyclization of Aryl and 2-Thienyl Vinyl Alcohols.
Jin, Jianwen; Zhao, Yichao; Gouranourimi, Ali; Ariafard, Alireza; Hong Chan, Philip Wai; Journal of the American Chemical Society 140 (2018) 5834–5841; doi:10.1021/jacs.8b02339

data_4132197
_publ_section_title
;
 Chiral Br\/onsted Acid Catalyzed Enantioselective Dehydrative
 Nazarov-Type Electrocyclization of Aryl and 2-Thienyl Vinyl Alcohols.
;
_journal_issue                   17
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5834
_journal_page_last               5841
_journal_paper_doi               10.1021/jacs.8b02339
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H29 N O4'
_chemical_formula_sum            'C28 H29 N O4'
_chemical_formula_weight         443.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-06-23
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.87(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.2640(11)
_cell_length_b                   20.199(4)
_cell_length_c                   11.328(2)
_cell_measurement_reflns_used    16218
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.377
_cell_measurement_theta_min      1.825
_cell_volume                     1186.7(4)
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1034
_diffrn_reflns_av_unetI/netI     0.0719
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16218
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.377
_diffrn_reflns_theta_min         1.825
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 1967 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.2(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4624
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0628
_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^)+(0.0949P)^2^+0.3717P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1678
_refine_ls_wR_factor_ref         0.1693
_reflns_Friedel_coverage         0.940
_reflns_Friedel_fraction_full    0.956
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                4469
_reflns_number_total             4624
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b02339_si_001.cif
_cod_data_source_block           2_a
_cod_original_cell_volume        1186.6(4)
_cod_database_code               4132197
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.984
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C20(H20), C17(H17), C27(H27), C19(H19), C24(H24), C23(H23), C26(H26),
 C9(H9), C6(H6), C8(H8), C7(H7), C11(H11)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C3(H3A,H3B,H3C), C28(H28A,H28B,H28C), C2(H2A,H2B,H2C),
 C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'