Insight into and Computational Studies of the Selective Synthesis of 6H-Dibenzo[b,h]xanthenes.
Carneiro, Paula F.; Pinto, Maria do Carmo F R; Marra, Roberta K. F.; Campos, Vinícius R; Resende, Jackson Antônio L C; Delarmelina, Maicon; Carneiro, José Walkimar M; Lima, Emerson S.; da Silva, Fernando de C; Ferreira, Vitor F.; The Journal of organic chemistry 81 (2016) 5525–5537; doi:10.1021/acs.joc.6b00864

data_4036903
_publ_section_title
;
 Insight into and Computational Studies of the Selective Synthesis of
 6H-Dibenzo[b,h]xanthenes.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5525
_journal_page_last               5537
_journal_paper_doi               10.1021/acs.joc.6b00864
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C33 H18 N2 O3'
_chemical_formula_sum            'C33 H18 N2 O3'
_chemical_formula_weight         490.49
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-05-16
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                81.299(2)
_cell_angle_beta                 66.4970(10)
_cell_angle_gamma                62.7020(10)
_cell_formula_units_Z            2
_cell_length_a                   10.6689(4)
_cell_length_b                   10.9978(5)
_cell_length_c                   11.8961(6)
_cell_measurement_reflns_used    7704
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.69
_cell_measurement_theta_min      2.32
_cell_volume                     1136.62(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'Photon 100 detector'
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker D8 Venture diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Quazar multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            31178
_diffrn_reflns_theta_full        25.71
_diffrn_reflns_theta_max         25.71
_diffrn_reflns_theta_min         2.09
_diffrn_source                   'Microfocus sealed tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABAS
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.431
_exptl_crystal_size_mid          0.251
_exptl_crystal_size_min          0.122
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0386
_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^)+(0.0548P)^2^+0.3431P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1088
_reflns_number_gt                3384
_reflns_number_total             4323
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b00864_si_002.cif
_cod_data_source_block           pfc103
_cod_database_code               4036903
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C5(H5), C6(H6), C24(H24), C16(H16), C23(H23), C18(H18),
 C25(H25), C15(H15), C26(H26), C17(H17), C33(H33), C32(H32), C29(H29), C31(H31),
  C30(H30)
;
_olex2_submission_special_instructions 'No special instructions were received'