Synthesis, Characterization, and Properties of Diazapyrenes via Bischler-Napieralski Reaction.
Han, Yi; Hu, Zhenzhu; Liu, Meifang; Li, Mengwei; Wang, Tingting; Chen, Yulan; The Journal of organic chemistry 84 (2019) 3953–3959; doi:10.1021/acs.joc.8b03096

data_4034296
_publ_section_title
;
 Synthesis, Characterization, and Properties of Diazapyrenes via
 Bischler-Napieralski Reaction.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3953
_journal_page_last               3959
_journal_paper_doi               10.1021/acs.joc.8b03096
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         '2(C8 H5 Br N)'
_chemical_formula_sum            'C16 H10 Br2 N2'
_chemical_formula_weight         390.08
_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
_audit_creation_date             2018-10-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
????
;
_cell_angle_alpha                110.57(3)
_cell_angle_beta                 103.01(3)
_cell_angle_gamma                93.22(3)
_cell_formula_units_Z            2
_cell_length_a                   7.9089(16)
_cell_length_b                   8.3573(17)
_cell_length_c                   11.052(2)
_cell_measurement_reflns_used    2143
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.8704
_cell_measurement_theta_min      2.0395
_cell_volume                     659.0(3)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      113.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_av_unetI/netI     0.0786
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6381
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.017
_diffrn_reflns_theta_max         25.017
_diffrn_reflns_theta_min         2.039
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.140
_exptl_absorpt_correction_T_max  0.5788
_exptl_absorpt_correction_T_min  0.1926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.966
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.257
_refine_diff_density_min         -0.660
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.934
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0343
_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^)+(0.0283P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0795
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1727
_reflns_number_total             2323
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03096_si_002.cif
_cod_data_source_block           r20171229a1
_cod_database_code               4034296
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.579
_shelx_estimated_absorpt_t_min   0.193
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C10(H10), C14(H14)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              22193
_shelx_hkl_checksum              7622
_olex2_submission_special_instructions 'No special instructions were received'