Bioinspired Collective Syntheses of Iboga-Type Indole Alkaloids.
Zhao, Gaoyuan; Xie, Xingang; Sun, Haiyu; Yuan, Ziyun; Zhong, Zhuliang; Tang, Shouchu; She, Xuegong; Organic letters 18 (2016) 2447–2450; doi:10.1021/acs.orglett.6b00989

data_1543825
_publ_section_title
;
 Bioinspired Collective Syntheses of Iboga-Type Indole Alkaloids.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2447
_journal_page_last               2450
_journal_paper_doi               10.1021/acs.orglett.6b00989
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C19 H20 N2 O, H2 O'
_chemical_formula_sum            'C19 H22 N2 O2'
_chemical_formula_weight         310.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-05-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                106.944(16)
_cell_angle_beta                 95.85(2)
_cell_angle_gamma                98.867(13)
_cell_formula_units_Z            2
_cell_length_a                   7.1942(16)
_cell_length_b                   10.7514(12)
_cell_length_c                   13.461(4)
_cell_measurement_reflns_used    1177
_cell_measurement_temperature    294.06(10)
_cell_measurement_theta_max      22.3730
_cell_measurement_theta_min      3.9710
_cell_volume                     972.1(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.06(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details
;
  1 omega   -9.00   23.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   77.0000   90.0000 16

  2 omega  -52.00   86.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854    0.0000 -150.0000 69

  3 omega   21.00   47.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -38.0000 -180.0000 13

  4 omega  -17.00   13.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000 -180.0000 15

  5 omega    7.00   61.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -99.0000  -30.0000 27

  6 omega   65.00   95.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854 -178.0000 -150.0000 15

  7 omega  -51.00    7.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -38.0000 -180.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0346760000
_diffrn_orient_matrix_UB_12      -0.0037405000
_diffrn_orient_matrix_UB_13      -0.0522459000
_diffrn_orient_matrix_UB_21      -0.0939725000
_diffrn_orient_matrix_UB_22      -0.0034855000
_diffrn_orient_matrix_UB_23      0.0120912000
_diffrn_orient_matrix_UB_31      0.0130434000
_diffrn_orient_matrix_UB_32      0.0701047000
_diffrn_orient_matrix_UB_33      0.0152848000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.1091
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_number            3740
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.496
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.060
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_platon_squeeze_details
;
;
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3740
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.1707
_refine_ls_R_factor_gt           0.0991
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1878P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2898
_refine_ls_wR_factor_ref         0.3492
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1702
_reflns_number_total             3740
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00989_si_002.cif
_cod_data_source_block           zhaogy_1125-sr
_cod_database_code               1543825
_reflns_odcompleteness_completeness 98.16
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O2(H2A,H2B)
2.b Ternary CH refined with riding coordinates:
 C13(H13)
2.c Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C14(H14A,H14B), C15(H15A,H15B), C10(H10A,H10B)
2.d Aromatic/amide H refined with riding coordinates:
 N1(H1), C17(H17), C5(H5), C2(H2), C4(H4), C3(H3)
2.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'