Catalytic Enantioselective Hetero-[6+4] and -[6+2] Cycloadditions for the Construction of Condensed Polycyclic Pyrroles, Imidazoles, and Pyrazoles.
Bertuzzi, Giulio; Thøgersen, Mathias Kirk; Giardinetti, Maxime; Vidal-Albalat, Andreu; Simon, Adam; Houk, K. N.; Jørgensen, Karl Anker; Journal of the American Chemical Society 141 (2019) 3288–3297; doi:10.1021/jacs.8b13659

data_4128459
_publ_section_title
;
 Catalytic Enantioselective Hetero-[6+4] and -[6+2] Cycloadditions for the
 Construction of Condensed Polycyclic Pyrroles, Imidazoles, and Pyrazoles.
;
_journal_issue                   7
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3288
_journal_page_last               3297
_journal_paper_doi               10.1021/jacs.8b13659
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C25 H19 N O2 S'
_chemical_formula_sum            'C25 H19 N O2 S'
_chemical_formula_weight         397.50
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_Int_Tables_number      19
_audit_creation_date             2018-10-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4263(3)
_cell_length_b                   12.1889(6)
_cell_length_c                   24.4609(13)
_cell_measurement_reflns_used    9998
_cell_measurement_temperature    100
_cell_measurement_theta_max      21.95
_cell_measurement_theta_min      2.63
_cell_volume                     1916.01(17)
_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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9971
_diffrn_measured_fraction_theta_max 0.9971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Ag K\a'
_diffrn_radiation_wavelength     0.56086
_diffrn_reflns_av_R_equivalents  0.0772
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            60380
_diffrn_reflns_theta_full        22.0525
_diffrn_reflns_theta_max         22.05
_diffrn_reflns_theta_min         1.31
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9566
_exptl_absorpt_correction_T_min  0.9068
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0913 before and 0.0495 after correction.
The Ratio of minimum to maximum transmission is 0.9479.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.3779
_exptl_crystal_description       Block
_exptl_crystal_F_000             832.4388
_exptl_crystal_size_max          0.303
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.175
_refine_diff_density_max         0.8979
_refine_diff_density_min         -0.3435
_refine_diff_density_rms         0.0650
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.10(13)
_refine_ls_d_res_high            0.7469
_refine_ls_d_res_low             12.2305
_refine_ls_goodness_of_fit_ref   1.0516
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0516
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0279P)^2^+1.1719P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0973
_reflns_Friedel_coverage         0.997
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              16
_reflns_limit_k_min              -16
_reflns_limit_l_max              32
_reflns_limit_l_min              -32
_reflns_number_gt                4066
_reflns_number_total             4816
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ja8b13659_si_001.cif
_cod_data_source_block           JDE23GB03
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               4128459
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11a,H11b), C10(H10a,H10b)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C16(H16), C15(H15), C17(H17), C1(H1), C19(H19), C3(H3),
 C25(H25), C18(H18), C24(H24), C21(H21), C22(H22), C23(H23)
;
_olex2_submission_special_instructions 'No special instructions were received'