Enantioselective Total Synthesis and Assignment of the Absolute Configuration of the Furo[3,2- a]carbazole Alkaloid Furoclausine-B.
Spindler, Benedikt; Kataeva, Olga; Knölker, Hans-Joachim; The Journal of organic chemistry 83 (2018) 15136–15143; doi:10.1021/acs.joc.8b02426

data_4034760
_publ_section_title
;
 Enantioselective Total Synthesis and Assignment of the Absolute
 Configuration of the Furo[3,2- a]carbazole Alkaloid Furoclausine-B.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              15136
_journal_page_last               15143
_journal_paper_doi               10.1021/acs.joc.8b02426
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H15 N O4'
_chemical_formula_sum            'C12 H15 N O4'
_chemical_formula_weight         237.25
_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   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.48940(10)
_cell_length_b                   11.0722(2)
_cell_length_c                   12.8612(2)
_cell_measurement_reflns_used    9996
_cell_measurement_temperature    198(2)
_cell_measurement_theta_max      68.09
_cell_measurement_theta_min      5.27
_cell_volume                     1208.91(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    Ortep
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      198(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'Bruker AXS Kappa Apex Duo'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14656
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.218
_diffrn_reflns_theta_min         5.271
_diffrn_source                   'microfocus X-ray-tube'
_exptl_absorpt_coefficient_mu    0.820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.368
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.090
_exptl_transmission_factor_max   0.3618
_exptl_transmission_factor_min   0.2666
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.111
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 886 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(3)
_refine_ls_extinction_coef       0.0025(6)
_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   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2207
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0276
_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^)+(0.0494P)^2^+0.1068P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0766
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                2157
_reflns_number_total             2207
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02426_si_002.cif
_cod_data_source_block           kno294
_cod_database_code               4034760
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.752
_shelx_estimated_absorpt_t_max   0.930
_shelx_res_checksum              83156
_shelx_hkl_checksum              21988