Acetic Acid Promoted Redox Annulations with Dual C-H Functionalization.
Zhu, Zhengbo; Seidel, Daniel; Organic letters 19 (2017) 2841–2844; doi:10.1021/acs.orglett.7b01047

data_1546239
_publ_section_title
;
 Acetic Acid Promoted Redox Annulations with Dual C-H Functionalization.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2841
_journal_page_last               2844
_journal_paper_doi               10.1021/acs.orglett.7b01047
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_sum            'C21 H20 N2'
_chemical_formula_weight         300.39
_space_group_crystal_system      trigonal
_space_group_IT_number           159
_space_group_name_Hall           'P 3 -2c'
_space_group_name_H-M_alt        'P 3 1 c'
_symmetry_space_group_name_Hall  'P 3 -2c'
_symmetry_space_group_name_H-M   'P 3 1 c'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   18.6655(11)
_cell_length_b                   18.6655(11)
_cell_length_c                   8.1126(5)
_cell_measurement_reflns_used    8205
_cell_measurement_temperature    195(2)
_cell_measurement_theta_max      30.46
_cell_measurement_theta_min      2.52
_cell_volume                     2447.8(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  SHELXL-2014/7
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      195(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11857
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.714
_diffrn_reflns_theta_min         2.182
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  .9999
_exptl_absorpt_correction_T_min  .8815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SAINT (SADABS)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_description       rod
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
; 
 Flack x determined using 1495 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -2.9(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4088
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0449
_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^)+(0.0486P)^2^+0.1210P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1035
_reflns_Friedel_coverage         0.991
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3718
_reflns_number_total             4088
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01047_si_004.cif
_cod_data_source_block           c21h20n2_P31c
_cod_database_code               1546239
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.990
_shelx_res_checksum              34962
_shelx_hkl_checksum              24822