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_1512333
_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 H20 N2 O, C H Cl3, H2 O'
_chemical_formula_sum            'C20 H23 Cl3 N2 O2'
_chemical_formula_weight         429.75
_chemical_melting_point          114.0(10)
_chemical_name_common            Tabertinggine
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.7462(2)
_cell_length_b                   9.3007(3)
_cell_length_c                   32.0517(9)
_cell_measurement_reflns_used    1601
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.25
_cell_measurement_theta_min      2.53
_cell_volume                     2011.06(10)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material
;  
SHELXL-97 (Sheldrick, 2008), enCIFer (Allen et al., 2004),
;
_computing_structure_refinement
;  
SHELXL97 (Sheldrick, 2008), Olex2 (Dolomanov & Puschmann, 2009)
;
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1101
_diffrn_reflns_av_sigmaI/netI    0.1006
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            18791
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.474
_exptl_absorpt_correction_T_max  0.9906
_exptl_absorpt_correction_T_min  0.8479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4605
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.951
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_gt           0.0588
_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^)+(0.0592P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1228
_reflns_number_gt                3332
_reflns_number_total             4605
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol4021404_si_001.cif
_cod_data_source_block           Tabertinggine
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '113-115' was changed to '114.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
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_cod_database_code               1512333