Highly Functionalized Tricyclic Oxazinanones via Pairwise Oxidative Dearomatization and N-Hydroxycarbamate Dehydrogenation: Molecular Diversity Inspired by Tetrodotoxin.
Good, Steffen N.; Sharpe, Robert J.; Johnson, Jeffrey S.; Journal of the American Chemical Society 139 (2017) 12422–12425; doi:10.1021/jacs.7b07745

data_4131640
_publ_section_title
;
 Highly Functionalized Tricyclic Oxazinanones via Pairwise Oxidative
 Dearomatization and N-Hydroxycarbamate Dehydrogenation: Molecular
 Diversity Inspired by Tetrodotoxin.
;
_journal_issue                   36
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12422
_journal_page_last               12425
_journal_paper_doi               10.1021/jacs.7b07745
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C29 H22 N4 O11'
_chemical_formula_sum            'C29 H22 N4 O11'
_chemical_formula_weight         602.50
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-05-06
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.176(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.461(3)
_cell_length_b                   12.567(2)
_cell_length_c                   12.991(2)
_cell_measurement_reflns_used    9656
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.45
_cell_measurement_theta_min      2.72
_cell_volume                     2653.0(8)
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0782
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            30174
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.488
_diffrn_reflns_theta_min         2.719
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.004
_exptl_absorpt_correction_T_max  0.98397
_exptl_absorpt_correction_T_min  0.81263
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0960 before and 0.0657 after correction.
The Ratio of minimum to maximum transmission is 0.7983.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_description       needle
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.606
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.041
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         5012
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0439
_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^)+(0.0471P)^2^+0.5983P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1092
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3554
_reflns_number_total             5012
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b07745_si_003.cif
_cod_data_source_block           x1605001
_cod_original_cell_volume        2652.9(8)
_cod_database_code               4131640
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.581
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C16(H16), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C32(H32A,H32B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C24(H24),
 C25(H25), C27(H27), C28(H28), C37(H37), C38(H38), C40(H40), C41(H41)
;
_shelx_res_checksum              74547
_shelx_hkl_checksum              46963
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-05-05
_olex2_date_sample_submission    2016-05-05
_olex2_submission_original_sample_id ER1728
_olex2_submission_special_instructions 'No special instructions were received'