Total synthesis of the tetracyclic indole alkaloid ht-13-B.
Zhang, Yilin; Hubbard, Jeremiah W.; Akhmedov, Novruz G.; Petersen, Jeffrey L.; Söderberg, Björn C G; The Journal of organic chemistry 80 (2015) 4783–4790; doi:10.1021/acs.joc.5b00433

data_4036194
_publ_section_title
;
 Total synthesis of the tetracyclic indole alkaloid ht-13-B.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4783
_journal_page_last               4790
_journal_paper_doi               10.1021/acs.joc.5b00433
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C16 H18 N2 O5'
_chemical_formula_weight         318.32
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 97.7471(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.5978(2)
_cell_length_b                   8.3479(2)
_cell_length_c                   12.4229(3)
_cell_measurement_temperature    296(2)
_cell_volume                     780.74(3)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker AXS D8 Venture fixed chi'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14410
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        27.539
_diffrn_reflns_theta_max         27.539
_diffrn_reflns_theta_min         2.948
_exptl_absorpt_coefficient_mu    0.102
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.486
_exptl_crystal_size_mid          0.374
_exptl_crystal_size_min          0.158
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1409 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.3(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3579
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0483P)^2^+0.1519P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.1029
_reflns_Friedel_coverage         0.867
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                3253
_reflns_number_total             3579
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00433_si_007.cif
_cod_data_source_block           bs3cms
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4036194
_shelx_estimated_absorpt_t_min   0.952
_shelx_estimated_absorpt_t_max   0.984
_shelxl_version_number           2013-4
_shelx_res_checksum              99107
_shelx_hkl_checksum              25769