Synthesis of NBN-Type Zigzag-Edged Polycyclic Aromatic Hydrocarbons: 1,9-Diaza-9a-boraphenalene as a Structural Motif.
Wang, Xinyang; Zhang, Fan; Schellhammer, Karl Sebastian; Machata, Peter; Ortmann, Frank; Cuniberti, Gianaurelio; Fu, Yubin; Hunger, Jens; Tang, Ruizhi; Popov, Alexey A.; Berger, Reinhard; Müllen, Klaus; Feng, Xinliang; Journal of the American Chemical Society 138 (2016) 11606–11615; doi:10.1021/jacs.6b04445

data_4125225
_publ_section_title
;
 Synthesis of NBN-Type Zigzag-Edged Polycyclic Aromatic Hydrocarbons:
 1,9-Diaza-9a-boraphenalene as a Structural Motif.
;
_journal_issue                   36
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11606
_journal_page_last               11615
_journal_paper_doi               10.1021/jacs.6b04445
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C42 H45 B N2'
_chemical_formula_sum            'C42 H45 B N2'
_chemical_formula_weight         588.61
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-10-06
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                92.270(2)
_cell_angle_beta                 92.092(2)
_cell_angle_gamma                93.949(2)
_cell_formula_units_Z            2
_cell_length_a                   9.3703(4)
_cell_length_b                   9.8045(4)
_cell_length_c                   17.2896(8)
_cell_measurement_reflns_used    8858
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.568
_cell_measurement_theta_min      2.351
_cell_volume                     1582.17(12)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0836
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            47381
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         2.084
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30
_diffrn_source_target            Mo
_diffrn_source_voltage           50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8717
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0652 before and 0.0558 after correction. The Ratio of minimum to maximum transmission is 0.8717. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of chloroform and methanol by slow evaporation'
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.234
_exptl_crystal_size_min          0.153
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         7632
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.950
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0736P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1244
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5449
_reflns_number_total             7632
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b04445_si_004.cif
_cod_data_source_block           wxy150727-2_100k
_cod_depositor_comments
'Adding full bibliography for 4125225--4125226.cif.'
_cod_database_code               4125225
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,
 H35B), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B), C40(H40A,H40B),
 C41(H41A,H41B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C8(H8), C9(H9), C10(H10), C13(H13), C15(H15),
 C16(H16), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26), C27(H27),
  C28(H28), C29(H29), C30(H30)
2.c Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C42(H42A,H42B,H42C)
;
_olex2_date_sample_data_collection 2015-10-05
_olex2_date_sample_submission    2015-09-17
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a glass fibre with two-component glue'
_olex2_submission_original_sample_id wxy150727-2
_olex2_submission_special_instructions 'No special instructions were received'