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_1544318
_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         C20H23N2O2I
_chemical_formula_sum            'C20 H23 I N2 O2'
_chemical_formula_weight         450.30
_chemical_melting_point          489(2)
_chemical_name_common            'Cononuridine methyl iodide'
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   7.6879(8)
_cell_length_b                   13.0251(14)
_cell_length_c                   18.905(2)
_cell_measurement_reflns_used    1529
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.09
_cell_measurement_theta_min      2.66
_cell_volume                     1893.1(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.0987
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5892
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.357
_diffrn_reflns_theta_min         1.899
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    1.707
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 - Bruker'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.020
_refine_diff_density_max         1.003
_refine_diff_density_min         -0.943
_refine_diff_density_rms         0.147
_refine_ls_abs_structure_details
;
 Flack x determined using 903 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3636
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.938
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0439
_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^)+(0.0425P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.1027
_reflns_Friedel_coverage         0.639
_reflns_Friedel_fraction_full    0.891
_reflns_Friedel_fraction_max     0.860
_reflns_number_gt                2899
_reflns_number_total             3636
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np6b00674_si_002.cif
_cod_data_source_block           Cononuridine_methyl_iodide
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '487-491 K' was changed to '489(2)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 1544317--1544318.cif.
;
_cod_original_cell_volume        1893.1(4)
_cod_database_code               1544318
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.726
_shelx_estimated_absorpt_t_max   0.967
_shelx_res_checksum              25606
_shelx_hkl_checksum              64264