Photoassisted Synthesis of Enantiopure Alkaloid Mimics Possessing Unprecedented Polyheterocyclic Cores
N.N. Bhuvan Kumar; Olga A. Mukhina; Andrei G. Kutateladze; Journal of the American Chemical Society 135 (2013) 9608–9611; doi:10.1021/ja4042109

data_4120045
_publ_contact_author_address
;Department of Chemistry and Biochemistry
University of Denver
FW Olin Hall, 202
2190 E. Iliff Ave
Denver, CO 80208
;
_publ_contact_author_email       akutatel.edu
_publ_contact_author_fax         303-871-2254
_publ_contact_author_name        'Andrei Kutateladze'
_publ_contact_author_phone       303-871-2995
_publ_section_title
;
 Photoassisted Synthesis of Enantiopure Alkaloid Mimics Possessing
 Unprecedented Polyheterocyclic Cores
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9608
_journal_page_last               9611
_journal_paper_doi               10.1021/ja4042109
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C26 H23 N3 O4 S'
_chemical_formula_sum            'C26 H23 N3 O4 S'
_chemical_formula_weight         473.53
_chemical_name_systematic
;
3R,7S,8S,11S-8-Hydroxy-3-phenyl-5-(4-methylbenzenesulfonylimino)
-9,10-benzo-2-oxo-1,4-diazatricyclo[5.3.1.0^4,11^]undec-9-ene 
;
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.075(2)
_cell_angle_beta                 110.344(2)
_cell_angle_gamma                93.560(2)
_cell_formula_units_Z            2
_cell_length_a                   9.7606(4)
_cell_length_b                   11.2605(4)
_cell_length_c                   13.1835(5)
_cell_measurement_reflns_used    9872
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.33
_cell_measurement_theta_min      2.25
_cell_volume                     1300.57(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 APEX II Diffractometer'
_diffrn_measurement_method       '\f and \w 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  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0089
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            67895
_diffrn_reflns_theta_full        25.36
_diffrn_reflns_theta_max         25.36
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.9643
_exptl_absorpt_correction_T_min  0.9190
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_description       Diamond
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.23
_platon_squeeze_details
;
;
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4757
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0599P)^2^+0.2510P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1087
_reflns_number_gt                4326
_reflns_number_total             4757
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja4042109_si_002_04.cif
_cod_data_source_block           12g
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4120045