Tabernaesines A-I, Cytotoxic Aspidosperma-Aspidosperma-Type Bisindole Alkaloids from <i>Tabernaemontana pachysiphon</i>.
Yi, Wen-Fang; Ding, Xiao; Chen, Yuan-Zhi; Adelakun, Tiwalade A.; Zhang, Yu; Hao, Xiao-Jiang; Journal of natural products  (2020) –; doi:10.1021/acs.jnatprod.9b00768

data_1559418
_publ_section_title
;
 Tabernaesines A-I, Cytotoxic Aspidosperma-Aspidosperma-Type Bisindole
 Alkaloids from <i>Tabernaemontana pachysiphon</i>.
;
_journal_name_full               'Journal of natural products'
_journal_paper_doi               10.1021/acs.jnatprod.9b00768
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C42 H48 N4 O4, C H2 Cl2, 2(H2 O)'
_chemical_formula_sum            'C43 H54 Cl2 N4 O6'
_chemical_formula_weight         793.80
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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                   11.2750(3)
_cell_length_b                   14.6945(5)
_cell_length_c                   24.4728(7)
_cell_measurement_reflns_used    9678
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.50
_cell_measurement_theta_min      3.51
_cell_volume                     4054.7(2)
_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-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.945
_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  0.0636
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19623
_diffrn_reflns_point_group_measured_fraction_full 0.894
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.585
_diffrn_reflns_theta_min         3.508
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       blcok
_exptl_crystal_F_000             1688
_exptl_crystal_size_max          1.050
_exptl_crystal_size_mid          0.900
_exptl_crystal_size_min          0.600
_exptl_transmission_factor_max   0.2732
_exptl_transmission_factor_min   0.0900
_refine_diff_density_max         1.533
_refine_diff_density_min         -1.117
_refine_diff_density_rms         0.152
_refine_ls_abs_structure_details
;
 Flack x determined using 2492 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.128(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     498
_refine_ls_number_reflns         6600
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0968
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1788P)^2^+11.2905P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2739
_refine_ls_wR_factor_ref         0.2747
_reflns_Friedel_coverage         0.667
_reflns_Friedel_fraction_full    0.816
_reflns_Friedel_fraction_max     0.799
_reflns_number_gt                6484
_reflns_number_total             6600
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00768_si_002.cif
_cod_data_source_block           cu_htb7_0m
_cod_database_code               1559418
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.245
_shelx_estimated_absorpt_t_max   0.401
_shelx_res_checksum              24442
_shelx_hkl_checksum              16588