Enantioselective synthesis of <i>Iboga</i> alkaloids and vinblastine <i>via</i> rearrangements of quaternary ammoniums.
Zhang, Yun; Xue, Yibin; Li, Gang; Yuan, Haosen; Luo, Tuoping; Chemical science 7 (2016) 5530–5536; doi:10.1039/c6sc00932h

data_1553642
_publ_section_title
;
 Enantioselective synthesis of <i>Iboga</i> alkaloids and vinblastine
 <i>via</i> rearrangements of quaternary ammoniums.
;
_journal_issue                   8
_journal_name_full               'Chemical science'
_journal_page_first              5530
_journal_page_last               5536
_journal_paper_doi               10.1039/c6sc00932h
_journal_volume                  7
_journal_year                    2016
_chemical_formula_moiety         'C18 H19 N3'
_chemical_formula_sum            'C18 H19 N3'
_chemical_formula_weight         277.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           41
_space_group_name_Hall           'A 2 -2ab'
_space_group_name_H-M_alt        'A e a 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-05-16
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-10-26 deposited with the CCDC.
2016-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   12.2491(9)
_cell_length_b                   35.949(3)
_cell_length_c                   13.0880(13)
_cell_measurement_reflns_used    4911
_cell_measurement_temperature    100.02(18)
_cell_measurement_theta_max      28.5210
_cell_measurement_theta_min      3.1760
_cell_volume                     5763.2(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100.02(18)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega   34.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017 -178.0000  -90.0000 64

  2 omega  -40.00  -13.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -57.0000  -90.0000 27

  3 omega  -18.00   19.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -38.0000   60.0000 37

  4 omega   -2.00   26.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  -99.0000 -120.0000 28

  5 omega  -36.00   22.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  -77.0000    0.0000 58
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0015519000
_diffrn_orient_matrix_UB_12      -0.0138871000
_diffrn_orient_matrix_UB_13      0.0384684000
_diffrn_orient_matrix_UB_21      0.0193888000
_diffrn_orient_matrix_UB_22      0.0133120000
_diffrn_orient_matrix_UB_23      0.0356358000
_diffrn_orient_matrix_UB_31      -0.0545346000
_diffrn_orient_matrix_UB_32      0.0043400000
_diffrn_orient_matrix_UB_33      0.0137169000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14143
_diffrn_reflns_point_group_measured_fraction_full 0.893
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_min         2.842
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_F_000             2368
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1634 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.6(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5020
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0588P)^2^+2.2613P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1160
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_full    0.781
_reflns_Friedel_fraction_max     0.764
_reflns_number_gt                4322
_reflns_number_total             5020
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc00932h2.cif
_cod_data_source_block           exp_5273
_cod_original_cell_volume        5763.2(8)
_cod_original_sg_symbol_Hall     'A 2 -2ac'
_cod_database_code               1553642
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C15 H20 N3'
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.989
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C13(H13), C14(H14), C15(H15), C29(H29), C31(H31), C33(H33), C34(H34)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B), C17(H17A,H17B),
 C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B), C30(H30A,H30B), C35(H35A,H35B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C20(H20), C21(H21), C22(H22), C23(H23),
 N1(H1), N4(H4A)
;
_olex2_submission_special_instructions 'No special instructions were received'