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_4036193
_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_absolute_configuration relative
_chemical_formula_sum            'C15 H18 N2 O'
_chemical_formula_weight         242.31
_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            4
_cell_length_a                   7.2130(3)
_cell_length_b                   12.9671(5)
_cell_length_c                   14.1141(6)
_cell_measurement_reflns_used    9556
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      3.14
_cell_volume                     1320.12(9)
_computing_data_collection       APEX2
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_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  0.0237
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25537
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.531
_diffrn_reflns_theta_min         2.886
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.569
_exptl_crystal_size_mid          0.541
_exptl_crystal_size_min          0.424
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details
;
 Flack x determined using 1151 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.3(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         3050
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0337
_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^)+(0.0527P)^2^+0.1162P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0931
_reflns_Friedel_coverage         0.728
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2808
_reflns_number_total             3050
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00433_si_005.cif
_cod_data_source_block           bs1cms_0m
_cod_database_code               4036193
_shelx_estimated_absorpt_t_min   0.957
_shelx_estimated_absorpt_t_max   0.968
_shelxl_version_number           2013-4
_shelx_res_checksum              3256
_shelx_hkl_checksum              12256