Ibogan, tacaman, and cytotoxic bisindole alkaloids from tabernaemontana. Cononusine, an iboga alkaloid with unusual incorporation of a pyrrolidone moiety.
Lim, Kuan-Hon; Raja, Vijay J.; Bradshaw, Tracey D.; Lim, Siew-Huah; Low, Yun-Yee; Kam, Toh-Seok; Journal of natural products 78 (2015) 1129–1138; doi:10.1021/acs.jnatprod.5b00117

data_1519686
_publ_section_title
;
 Ibogan, tacaman, and cytotoxic bisindole alkaloids from tabernaemontana.
 Cononusine, an iboga alkaloid with unusual incorporation of a pyrrolidone
 moiety.
;
_journal_issue                   5
_journal_name_full               'Journal of natural products'
_journal_page_first              1129
_journal_page_last               1138
_journal_paper_doi               10.1021/acs.jnatprod.5b00117
_journal_volume                  78
_journal_year                    2015
_chemical_formula_moiety         'C42 H52 N4 O4, C H Cl3. 3H2 O'
_chemical_formula_sum            'C43 H59 Cl3 N4 O7'
_chemical_formula_weight         850.29
_chemical_temperature_decomposition_gt 463
_space_group_crystal_system      hexagonal
_space_group_IT_number           170
_space_group_name_Hall           'P 65'
_space_group_name_H-M_alt        'P 65'
_symmetry_space_group_name_Hall  'P 65'
_symmetry_space_group_name_H-M   'P 65'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   25.987(3)
_cell_length_b                   25.987(3)
_cell_length_c                   12.7789(12)
_cell_measurement_reflns_used    2168
_cell_measurement_temperature    100.1(5)
_cell_measurement_theta_max      18.9670
_cell_measurement_theta_min      3.5310
_cell_volume                     7473.7(14)
_computing_cell_refinement       'CrysAlis PRO'
_computing_data_collection       'CrysAlis PRO  (Agilent, 2010)'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.1(5)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_av_unetI/netI     0.1270
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13170
_diffrn_reflns_point_group_measured_fraction_full 0.787
_diffrn_reflns_point_group_measured_fraction_max 0.787
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         3.149
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_description       block
_exptl_crystal_F_000             2712
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 954 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     517
_refine_ls_number_reflns         6910
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.184
_refine_ls_R_factor_all          0.1952
_refine_ls_R_factor_gt           0.1011
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2296
_refine_ls_wR_factor_ref         0.2847
_reflns_Friedel_coverage         0.572
_reflns_Friedel_fraction_full    0.602
_reflns_Friedel_fraction_max     0.602
_reflns_number_gt                3366
_reflns_number_total             6910
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np5b00117_si_002.cif
_cod_data_source_block           exp_4715
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_temperature_decomposition_gt' since the value was
specified 'more than' ('>') a certain temperature. The value '>463
dec' was changed to '463' - it should be numeric and without a unit
designator.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 1519686.cif.
;
_cod_original_cell_volume        7473.6(17)
_cod_database_code               1519686
_shelxl_version_number           2014/6
_shelx_res_checksum              55226
_shelx_hkl_checksum              45675