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_1553640
_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_absolute_configuration syn
_chemical_formula_moiety         'C19 H18 N2 O3'
_chemical_formula_sum            'C19 H18 N2 O3'
_chemical_formula_weight         322.35
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_space_group_name_H-M_alt        'P 43 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-09-28
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_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            8
_cell_length_a                   9.37666(19)
_cell_length_b                   9.37666(19)
_cell_length_c                   36.6305(12)
_cell_measurement_reflns_used    2261
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      65.5110
_cell_measurement_theta_min      4.8390
_cell_volume                     3220.62(14)
_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
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      180.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9987
_diffrn_measured_fraction_theta_max 0.9370
_diffrn_measurement_details
;
  1 omega  -60.00   33.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7931   57.0000 -120.0000 93

  2 omega   47.00   81.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.9350  -30.0000  -60.0000 34

  3 omega  101.00  162.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.9350  125.0000  -90.0000 61

  4 omega   62.00  159.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       90.9350   30.0000  -90.0000 97
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0022823000
_diffrn_orient_matrix_UB_12      0.0846279000
_diffrn_orient_matrix_UB_13      0.0360541000
_diffrn_orient_matrix_UB_21      -0.0533230000
_diffrn_orient_matrix_UB_22      -0.1338542000
_diffrn_orient_matrix_UB_23      0.0202672000
_diffrn_orient_matrix_UB_31      0.1551892000
_diffrn_orient_matrix_UB_32      -0.0446541000
_diffrn_orient_matrix_UB_33      0.0075538000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.939
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            5710
_diffrn_reflns_point_group_measured_fraction_full 0.890
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         65.529
_diffrn_reflns_theta_min         4.829
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67835
_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_colour            white
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_F_000             1360
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM MeOH'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 816 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2598
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0510P)^2^+0.5727P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1052
_reflns_Friedel_coverage         0.541
_reflns_Friedel_fraction_full    0.812
_reflns_Friedel_fraction_max     0.860
_reflns_number_gt                2382
_reflns_number_total             2598
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc00932h2.cif
_cod_data_source_block           1
_cod_original_cell_volume        3220.62(17)
_cod_database_code               1553640
_chemical_oxdiff_formula         'C19 H20 O3 N2'
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C7(H7A,H7B), C8(H8A,H8B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
2.e :
 C19(H19)
;
_shelx_estimated_absorpt_t_max   0.930
_shelx_estimated_absorpt_t_min   0.866
_shelxl_version_number           2013-3