Total syntheses of the monoterpene indole alkaloids (±)-alstilobanine A and E and (±)-angustilodine.
Feng, Yiqing; Majireck, Max M.; Weinreb, Steven M.; The Journal of organic chemistry 79 (2014) 7–24; doi:10.1021/jo402495q

data_4029060
_publ_section_title
;
 Total syntheses of the monoterpene indole alkaloids (+-)-alstilobanine A
 and E and (+-)-angustilodine.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7
_journal_page_last               24
_journal_paper_doi               10.1021/jo402495q
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C36 H53 N3 O7 S Si, 2.5H2O'
_chemical_formula_sum            'C32 H40 N3 O9.44 S Si'
_chemical_formula_weight         727.31
_chemical_melting_point          402.0(10)
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   31.296(5)
_cell_length_b                   31.296(5)
_cell_length_c                   18.216(3)
_cell_measurement_reflns_used    7817
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.089
_cell_measurement_theta_min      2.249
_cell_volume                     17841(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'SMART APEX CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0777
_diffrn_reflns_av_sigmaI/netI    0.0564
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            73109
_diffrn_reflns_theta_full        28.84
_diffrn_reflns_theta_max         28.84
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_T_max  0.9746
_exptl_absorpt_correction_T_min  0.9719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.009
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             5736
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.709
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       0.0016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         11604
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.2274
_refine_ls_R_factor_gt           0.1145
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3291
_refine_ls_wR_factor_ref         0.3987
_reflns_number_gt                3414
_reflns_number_total             11604
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402495q_si_002.cif
_cod_data_source_block           yuf1t
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '401-403' was changed to '402.0(10)'
- the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Tetragonal' changed to
'tetragonal' according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      I4(1)/a
_cod_database_code               4029060