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_1553641
_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         '0.5(C H Cl3), C19 H24 N2'
_chemical_formula_sum            'C19.5 H24.5 Cl1.5 N2'
_chemical_formula_weight         340.08
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-05-04
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 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                 90.541(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.0230(11)
_cell_length_b                   21.0779(16)
_cell_length_c                   12.8028(9)
_cell_measurement_reflns_used    3295
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      27.8940
_cell_measurement_theta_min      3.2870
_cell_volume                     3514.2(5)
_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
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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      180.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.930
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_details
;
  1 omega  -54.00   36.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -57.0000  150.0000 90

  2 omega  -81.00    0.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  -57.0000  -90.0000 81
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0125775000
_diffrn_orient_matrix_UB_12      -0.0321887000
_diffrn_orient_matrix_UB_13      0.0099332000
_diffrn_orient_matrix_UB_21      -0.0525650000
_diffrn_orient_matrix_UB_22      -0.0068573000
_diffrn_orient_matrix_UB_23      0.0087522000
_diffrn_orient_matrix_UB_31      -0.0067364000
_diffrn_orient_matrix_UB_32      -0.0070122000
_diffrn_orient_matrix_UB_33      -0.0538028000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_unetI/netI     0.0952
_diffrn_reflns_Laue_measured_fraction_full 0.930
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12429
_diffrn_reflns_point_group_measured_fraction_full 0.930
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         3.129
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61316
_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            'light yellow'
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             1448
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CHCl3, Acetone'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.764
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     429
_refine_ls_number_reflns         5920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.1306
_refine_ls_R_factor_gt           0.0896
_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^)+(0.1042P)^2^+3.0406P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2077
_refine_ls_wR_factor_ref         0.2393
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3872
_reflns_number_total             5920
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc00932h2.cif
_cod_data_source_block           exp_5207
_cod_depositor_comments
;

2022-05-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     'C H Cl3, 2(C19 H24 N2)'
_cod_original_formula_sum        'C39 H49 Cl3 N4'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     680.17
_cod_database_code               1553641
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C19 H10 N2'
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.957
_reflns_odcompleteness_completeness 99.21
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C39(H39), C31(H31), C35(H35), C12(H12), C11(H11), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C28(H28A,H28B), C34(H34A,H34B), C37(H37A,H37B), C36(H36A,
 H36B), C33(H33A,H33B), C9(H9A,H9B), C18(H18A,H18B), C16(H16A,H16B), C15(H15A,
 H15B), C14(H14A,H14B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C23(H23), C22(H22), C24(H24), C21(H21), N1(H1), C4(H4), C5(H5),
 C3(H3A), C2(H2)
2.d Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C19(H19A,H19B,H19C)
;
_olex2_submission_special_instructions 'No special instructions were received'