Total syntheses of the bilirubin oxidation end product Z-BOX C and its isomeric form Z-BOX D.
Schulze, Daniel; Traber, Juliane; Ritter, Marcel; Görls, Helmar; Pohnert, Georg; Westerhausen, Matthias; Organic & biomolecular chemistry 17 (2019) 6489–6496; doi:10.1039/c9ob01117j

data_7156913
_publ_section_title
;
 Total syntheses of the bilirubin oxidation end product Z-BOX C and its
 isomeric form Z-BOX D.
;
_journal_issue                   26
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6489
_journal_page_last               6496
_journal_paper_doi               10.1039/c9ob01117j
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C15 H15 N O6 S'
_chemical_formula_sum            'C15 H15 N O6 S'
_chemical_formula_weight         337.34
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2019-05-13 deposited with the CCDC.    2019-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                68.144(3)
_cell_angle_beta                 73.035(3)
_cell_angle_gamma                76.069(3)
_cell_formula_units_Z            2
_cell_length_a                   7.7698(4)
_cell_length_b                   9.8328(6)
_cell_length_c                   11.4487(7)
_cell_measurement_reflns_used    6957
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.97
_cell_volume                     767.82(8)
_computing_cell_refinement       DENZO
_computing_data_collection       COLLECT
_computing_data_reduction        DENZO
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_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  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6957
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2002'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.108
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.088
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3396
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0215P)^2^+0.6131P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0985
_reflns_number_gt                3006
_reflns_number_total             3396
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ob01117j2.cif
_cod_data_source_block           FO6807
_cod_depositor_comments
'Adding full bibliography for 7156910--7156913.cif.'
_cod_database_code               7156913