Leucophyllidine, a cytotoxic bisindole alkaloid constituted from the union of an eburnan and a new vinylquinoline alkaloid.
Gan, Chew-Yan; Robinson, Ward T.; Etoh, Tadahiro; Hayashi, Masahiko; Komiyama, Kanki; Kam, Toh-Seok; Organic letters 11 (2009) 3962–3965; doi:10.1021/ol9016172

data_1504128
_publ_section_title
;
 Leucophyllidine, a cytotoxic bisindole alkaloid constituted from the
 union of an eburnan and a new vinylquinoline alkaloid.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              3962
_journal_page_last               3965
_journal_paper_doi               10.1021/ol9016172
_journal_volume                  11
_journal_year                    2009
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C38 H44 N4 O, C4 H8 O2'
_chemical_formula_sum            'C42 H52 N4 O3'
_chemical_formula_weight         660.88
_chemical_melting_point          216.0(10)
_chemical_name_common            Leucophylline
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.811(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.7151(3)
_cell_length_b                   8.5294(3)
_cell_length_c                   17.2463(5)
_cell_measurement_reflns_used    4219
_cell_measurement_temperature    117(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.50
_cell_volume                     1770.50(9)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material
;  
SHELXL-97 (Sheldrick, 2008), enCIFer (Allen et al., 2004),
;
_computing_structure_refinement
;  
SHELXL97 (Sheldrick, 2008), 
;
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      117(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       '\w 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  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16952
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.69
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     447
_refine_ls_number_reflns         4335
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0489
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0842P)^2^+0.5872P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1375
_reflns_number_gt                3796
_reflns_number_total             4335
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol9016172_si_002.cif
_cod_data_source_block           gan_734_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '215-217' was changed to '216.0(10)'
- the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1504128