Bipleiophylline, an unprecedented cytotoxic bisindole alkaloid constituted from the bridging of two indole moieties by an aromatic spacer unit.
Kam, Toh-Seok; Tan, Shin-Jowl; Ng, Seik-Weng; Komiyama, Kanki; Organic letters 10 (2008) 3749–3752; doi:10.1021/ol801354s

data_1504817
_publ_section_title
;
 Bipleiophylline, an unprecedented cytotoxic bisindole alkaloid
 constituted from the bridging of two indole moieties by an aromatic
 spacer unit.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              3749
_journal_page_last               3752
_journal_paper_doi               10.1021/ol801354s
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C47 H46 N4 O8. C2 H6 O'
_chemical_formula_sum            'C49 H52 N4 O9'
_chemical_formula_weight         840.95
_chemical_melting_point_gt       220
_chemical_name_common            Bipleiophylline
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                79.1190(10)
_cell_angle_beta                 81.7560(10)
_cell_angle_gamma                72.9240(10)
_cell_formula_units_Z            1
_cell_length_a                   9.16020(10)
_cell_length_b                   9.9973(2)
_cell_length_c                   12.4147(2)
_cell_measurement_reflns_used    6941
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      31.5939
_cell_measurement_theta_min      2.1571
_cell_volume                     1062.55(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16501
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale red'
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'triangular plate'
_exptl_crystal_F_000             446
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.883
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     566
_refine_ls_number_reflns         4841
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0569
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1161P)^2^+0.3230P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1569
_refine_ls_wR_factor_ref         0.1707
_reflns_number_gt                4190
_reflns_number_total             4841
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol801354s_si_001.cif
_cod_data_source_block           biple-renumbering
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_melting_point_gt' since the value was specified 'more
than' ('>') a certain temperature. The value '>220' was changed to
'220' - it should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_Hall     P1
_cod_original_sg_symbol_H-M      P1
_cod_database_code               1504817