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_1544317
_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         'C22 H29 I N2 O5'
_chemical_formula_sum            'C22 H29 I N2 O5'
_chemical_formula_weight         528.37
_chemical_name_common            'vernavosine methyl iodide'
_chemical_temperature_decomposition_gt 452
_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                   8.4155(5)
_cell_length_b                   10.1342(6)
_cell_length_c                   25.9099(15)
_cell_measurement_reflns_used    5399
_cell_measurement_temperature    100.2(8)
_cell_measurement_theta_max      29.9090
_cell_measurement_theta_min      3.4920
_cell_volume                     2209.7(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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(8)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            13272
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.288
_diffrn_reflns_theta_min         2.886
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.485
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78746
_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            'clear light yellow'
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_description       needle
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.3000
_exptl_crystal_size_mid          0.0200
_exptl_crystal_size_min          0.0200
_refine_diff_density_max         0.983
_refine_diff_density_min         -0.776
_refine_diff_density_rms         0.117
_refine_ls_abs_structure_details
;
 Flack x determined using 2026 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         5813
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0386P)^2^+0.7528P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0861
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.827
_reflns_number_gt                5368
_reflns_number_total             5813
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np6b00674_si_004.cif
_cod_data_source_block           Vernavosine_methyl_iodide
_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 '>452 K
dec' was changed to '452' - it should be numeric and without a unit
designator.

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

 Adding full bibliography for 1544317--1544318.cif.
;
_cod_database_code               1544317
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              10881
_shelx_hkl_checksum              95987