Total Synthesis of the Caged Indole Alkaloid Arboridinine Enabled by aza-Prins and Metal-Mediated Cyclizations.
Gan, Pei; Pitzen, Jennifer; Qu, Pei; Snyder, Scott A.; Journal of the American Chemical Society  (2018) –; doi:10.1021/jacs.7b07724

data_4127007
_publ_section_title
;
 Total Synthesis of the Caged Indole Alkaloid Arboridinine Enabled by
 aza-Prins and Metal-Mediated Cyclizations.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b07724
_journal_year                    2018
_chemical_formula_moiety         'C18 H19 Cl N2 O'
_chemical_formula_sum            'C18 H19 Cl N2 O'
_chemical_formula_weight         314.80
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2016-06-10
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.3950(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7605(5)
_cell_length_b                   11.0783(4)
_cell_length_c                   12.4037(5)
_cell_measurement_reflns_used    9969
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.61
_cell_measurement_theta_min      2.47
_cell_volume                     1476.03(11)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.01
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24612
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.743
_diffrn_reflns_theta_min         2.467
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.7030
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1204 before and 0.0460 after correction.
The Ratio of minimum to maximum transmission is 0.9426.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3687
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0365
_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^)+(0.0412P)^2^+0.7347P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0886
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2975
_reflns_number_total             3687
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b07724_si_003.cif
_cod_data_source_block           0247_peigan
_cod_database_code               4127007
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.921
_olex2_refinement_description
;
;
_shelx_res_checksum              71752
_shelx_hkl_checksum              90417
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'