Unified strategy to monoterpene indole alkaloids: total syntheses of (±)-goniomitine, (±)-1,2-dehydroaspidospermidine, (±)-aspidospermidine, (±)-vincadifformine, and (±)-kopsihainanine a.
Wagnières, Olivier; Xu, Zhengren; Wang, Qian; Zhu, Jieping; Journal of the American Chemical Society 136 (2014) 15102–15108; doi:10.1021/ja509329x

data_4122798
_publ_section_title
;
 Unified strategy to monoterpene indole alkaloids: total syntheses of
 (+-)-goniomitine, (+-)-1,2-dehydroaspidospermidine,
 (+-)-aspidospermidine, (+-)-vincadifformine, and (+-)-kopsihainanine a.
;
_journal_issue                   42
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15102
_journal_page_last               15108
_journal_paper_doi               10.1021/ja509329x
_journal_volume                  136
_journal_year                    2014
_chemical_formula_moiety         'C25 H29 N3 O6 S'
_chemical_formula_sum            'C25 H29 N3 O6 S'
_chemical_formula_weight         499.57
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
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_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2013-06-27 # Formatted by publCIF
;
_cell_angle_alpha                86.976(4)
_cell_angle_beta                 78.153(4)
_cell_angle_gamma                73.826(4)
_cell_formula_units_Z            2
_cell_length_a                   8.0074(3)
_cell_length_b                   11.6089(6)
_cell_length_c                   13.7965(8)
_cell_measurement_reflns_used    5688
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      72.4100
_cell_measurement_theta_min      3.9460
_cell_volume                     1205.47(11)
_computing_cell_refinement
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      140(2)
_diffrn_detector_area_resol_mean 10.2665
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_av_sigmaI/netI    0.0171
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8180
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         73.00
_diffrn_reflns_theta_min         3.96
_exptl_absorpt_coefficient_mu    1.589
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4658
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0521P)^2^+0.5453P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.0977
_reflns_number_gt                4456
_reflns_number_total             4658
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja509329x_si_001.cif
_cod_data_source_block           ow331
_cod_depositor_comments          'Adding full bibliography for 4122798.cif.'
_cod_original_cell_volume        1205.46(10)
_cod_database_code               4122798