Sequential Oxidative and Reductive Radical Cyclization Approach toward Asperparaline C and Synthesis of Its 8-Oxo Analogue.
Amatov, Tynchtyk; Pohl, Radek; Cisařová, Ivana; Jahn, Ullrich; Organic letters 19 (2017) 1152–1155; doi:10.1021/acs.orglett.7b00187

data_1545278
_publ_section_title
;
 Sequential Oxidative and Reductive Radical Cyclization Approach toward
 Asperparaline C and Synthesis of Its 8-Oxo Analogue.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1152
_journal_page_last               1155
_journal_paper_doi               10.1021/acs.orglett.7b00187
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesized by the authors'
_chemical_formula_moiety         'C19 H25 N3 O4'
_chemical_formula_sum            'C19 H25 N3 O4'
_chemical_formula_weight         359.42
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 101.6930(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.3152(3)
_cell_length_b                   16.8108(8)
_cell_length_c                   8.4777(4)
_cell_measurement_reflns_used    9789
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      72.1275
_cell_measurement_theta_min      5.9447
_cell_volume                     881.35(7)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection       'Bruker Instrument Service vV6.2.1'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            21469
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.121
_diffrn_reflns_theta_min         5.328
_diffrn_source                   'I\mS  micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.785
_exptl_absorpt_correction_T_max  0.86
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       prism
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.268
_exptl_crystal_size_mid          0.247
_exptl_crystal_size_min          0.203
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1624 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_coef       0.0165(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3443
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0271
_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^)+(0.0326P)^2^+0.2197P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0681
_reflns_Friedel_coverage         0.914
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                3431
_reflns_number_total             3443
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00187_si_005.cif
_cod_data_source_block           cu_tsyn774_01_jahn
_cod_depositor_comments
'Adding full bibliography for 1545277--1545278.cif.'
_cod_original_cell_volume        881.34(7)
_cod_database_code               1545278
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.817
_shelx_estimated_absorpt_t_max   0.857
_shelx_res_checksum              62919
_shelx_hkl_checksum              46619