Synthesis of the Tetracyclic Core (ABCE Rings) of Daphenylline
Bowen Fang; Huaiji Zheng; Changgui Zhao; Peng Jing; Huilin Li; Xingang Xie; Xuegong She; Journal of Organic Chemistry 77 (2012) 8367–8373; doi:10.1021/jo301533f

data_4027523
_publ_section_title
;
 Synthesis of the Tetracyclic Core (ABCE Rings) of Daphenylline
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8367
_journal_page_last               8373
_journal_paper_doi               10.1021/jo301533f
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C21 H22 N2 O7 S'
_chemical_formula_weight         446.47
_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                74.892(5)
_cell_angle_beta                 75.847(5)
_cell_angle_gamma                80.987(5)
_cell_formula_units_Z            2
_cell_length_a                   7.866(4)
_cell_length_b                   11.435(6)
_cell_length_c                   13.934(7)
_cell_measurement_reflns_used    2682
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.68
_cell_volume                     1167.5(10)
_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_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0559
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7430
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.68
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.9631
_exptl_absorpt_correction_T_min  0.9512
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_platon_squeeze_details
;
;
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4237
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0533
_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^)+(0.0901P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1427
_refine_ls_wR_factor_ref         0.1585
_reflns_number_gt                2874
_reflns_number_total             4237
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301533f_si_003.cif
_cod_data_source_block           p-1
_cod_original_cell_volume        1167.6(10)
_cod_database_code               4027523