Voatinggine and Tabertinggine, Pentacyclic Indole Alkaloids Derived from an Iboga Precursor via a Common Cleavamine-Type Intermediate
Nge, Choy-Eng; Gan, Chew-Yan; Low, Yun-Yee; Thomas, Noel F.; Kam, Toh-Seok; Organic Letters 15 (2013) 4774–; doi:10.1021/ol4021404

data_1512332
_publ_section_title
;
 Voatinggine and Tabertinggine, Pentacyclic Indole Alkaloids Derived from
 an Iboga Precursor via a Common Cleavamine-Type Intermediate
;
_journal_issue                   18
_journal_name_full               'Organic Letters'
_journal_page_first              4774
_journal_paper_doi               10.1021/ol4021404
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H22 N2 O2'
_chemical_formula_sum            'C19 H22 N2 O2'
_chemical_formula_weight         310.39
_chemical_melting_point          187.0(10)
_chemical_name_common            Voatinggine
_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                 102.188(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.6564(3)
_cell_length_b                   8.3932(2)
_cell_length_c                   9.8414(3)
_cell_measurement_reflns_used    3805
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.0510
_cell_measurement_theta_min      4.5929
_cell_volume                     779.65(4)
_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-97 (Sheldrick, 2008), Olex2 (Dolomanov & Puschmann, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type
'Agilent Technologies SuperNova Dual diffractometer with Atlas detector'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_sigmaI/netI    0.0147
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5115
_diffrn_reflns_theta_full        74.22
_diffrn_reflns_theta_max         74.22
_diffrn_reflns_theta_min         4.60
_exptl_absorpt_coefficient_mu    0.687
_exptl_absorpt_correction_T_max  0.9864
_exptl_absorpt_correction_T_min  0.8749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis PRO (Agilent, 2010)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 1384 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.17(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3066
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0373
_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^)+(0.0764P)^2^+0.1416P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1064
_reflns_number_gt                3040
_reflns_number_total             3066
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol4021404_si_001.cif
_cod_data_source_block           Voatinggine
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '186-188' was changed to '187.0(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 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1512332