A Hexacyclic, Iboga-Derived Monoterpenoid Indole with a Contracted Tetrahydroazepine C-Ring and Incorporation of an Isoxazolidine Moiety, a Seco-Corynanthean, an Aspidosperma-Aspidosperma Bisindole with Anticancer Properties, and the Absolute Configuration of the Pyridopyrimidine Indole Alkaloid, Vernavosine.
Nge, Choy-Eng; Sim, Kae-Shin; Lim, Siew-Huah; Thomas, Noel F.; Low, Yun-Yee; Kam, Toh-Seok; Journal of natural products 79 (2016) 2709–2717; doi:10.1021/acs.jnatprod.6b00674

data_1544484
_publ_section_title
;
 A Hexacyclic, Iboga-Derived Monoterpenoid Indole with a Contracted
 Tetrahydroazepine C-Ring and Incorporation of an Isoxazolidine Moiety, a
 Seco-Corynanthean, an Aspidosperma-Aspidosperma Bisindole with Anticancer
 Properties, and the Absolute Configuration of the Pyridopyrimidine Indole
 Alkaloid, Vernavosine.
;
_journal_issue                   10
_journal_name_full               'Journal of natural products'
_journal_page_first              2709
_journal_page_last               2717
_journal_paper_doi               10.1021/acs.jnatprod.6b00674
_journal_volume                  79
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         C44H50N4O10.CH3OH
_chemical_formula_sum            'C45 H54 N4 O11'
_chemical_formula_weight         826.92
_chemical_name_common            Conofolidine
_chemical_temperature_decomposition_gt 476
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_space_group_name_H-M_alt        'P 43 21 2'
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.2628(3)
_cell_length_b                   16.2628(3)
_cell_length_c                   35.9975(10)
_cell_measurement_reflns_used    11643
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.0170
_cell_measurement_theta_min      3.9630
_cell_volume                     9520.6(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'enCIFer (Allen et al., 2004)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 5.2020
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            38161
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.911
_diffrn_reflns_theta_min         3.844
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.682
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52407
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_description       prism
_exptl_crystal_F_000             3520
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 2304 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.416
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     550
_refine_ls_number_reflns         9522
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.416
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0808
_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^+0.4537P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2285
_refine_ls_wR_factor_ref         0.2397
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                6935
_reflns_number_total             9522
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np6b00674_si_003.cif
_cod_data_source_block           Conofolidine
_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 ' >476 K
dec' was changed to '476' - it should be numeric and without a unit
designator.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_cell_volume        9520.6(5)
_cod_database_code               1544484
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              83427
_shelx_hkl_checksum              33887