Catalytic Asymmetric Construction of the Tryptanthrin Skeleton via an Enantioselective Decarboxylative [4 + 2] Cyclization.
Mei, Guang-Jian; Bian, Chen-Yu; Li, Guo-Hao; Xu, Shao-Li; Zheng, Wen-Qin; Shi, Feng; Organic letters 19 (2017) 3219–3222; doi:10.1021/acs.orglett.7b01336

data_1556056
_publ_section_title
;
 Catalytic Asymmetric Construction of the Tryptanthrin Skeleton via an
 Enantioselective Decarboxylative [4 + 2] Cyclization.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3219
_journal_page_last               3222
_journal_paper_doi               10.1021/acs.orglett.7b01336
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17.5 H14 N2 O1.5'
_chemical_formula_weight         276.30
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.1969(2)
_cell_length_b                   9.8840(3)
_cell_length_c                   38.6328(12)
_cell_measurement_reflns_used    6073
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      137.032
_cell_measurement_theta_min      9.156
_cell_volume                     2748.11(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.933
_diffrn_measured_fraction_theta_max 0.975
_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  0.0392
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.933
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            12574
_diffrn_reflns_point_group_measured_fraction_full 0.925
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         65.486
_diffrn_reflns_theta_min         4.578
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
; 
 Flack x determined using 1763 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.08(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         4605
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0556P)^2^+1.1177P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1077
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    0.915
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                4376
_reflns_number_total             4605
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01336_si_002.cif
_cod_data_source_block           cu_dm16746_0m
_cod_depositor_comments
;

2022-05-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum        'C35 H28 N4 O3'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     552.61
_cod_database_code               1556056
_shelx_estimated_absorpt_t_min   0.874
_shelx_estimated_absorpt_t_max   0.928
_shelxl_version_number           2013-4
_shelx_res_checksum              23704
_shelx_hkl_checksum              24935