Copper-Catalyzed Nitration of Electron-Deficient BN-Naphthalene
Fang, Xiangdong; Chemical Communications  (2023) –; doi:10.1039/D3CC04359B

data_7132163
_publ_section_title
;
 Copper-Catalyzed Nitration of Electron-Deficient BN-Naphthalene
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04359B
_journal_year                    2023
_chemical_formula_moiety         'C8 H6 B I2 N'
_chemical_formula_sum            'C8 H6 B I2 N'
_chemical_formula_weight         380.75
_chemical_melting_point          436.35
_chemical_name_systematic        1,8-Diiodo-9,10-BN-Naphthalene
_chemical_properties_physical    Light-sensitive,Photo-sensitive
_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     dual
_audit_creation_date             2022-12-15
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_audit_update_record
;
2023-08-22 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                109.617(9)
_cell_angle_beta                 106.009(9)
_cell_angle_gamma                102.214(7)
_cell_formula_units_Z            6
_cell_length_a                   8.561(4)
_cell_length_b                   13.824(6)
_cell_length_c                   14.980(5)
_cell_measurement_reflns_used    8550
_cell_measurement_temperature    283(2)
_cell_measurement_theta_max      25.791
_cell_measurement_theta_min      2.628
_cell_volume                     1511.9(11)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      283.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-III CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25929
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.029
_diffrn_reflns_theta_min         2.712
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.183
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.4908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1326 before and 0.0632 after correction.
The Ratio of minimum to maximum transmission is 0.6585.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.509
_exptl_crystal_description       sheet
_exptl_crystal_F_000             1032
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.139
_refine_diff_density_min         -1.801
_refine_diff_density_rms         0.183
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5961
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0487
_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^)+(0.0347P)^2^+7.8748P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1142
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3878
_reflns_number_total             5961
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04359b2.cif
_cod_data_source_block           221205a_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '163.2oC' was changed to
'436.35' -- it was converted from degrees Celsius (C) to kelvins (K).

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

2025-01-11
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C24 H18 B3 I6 N3'
_cod_original_formula_weight         1142.24
_cod_original_formula_moiety         '3(C8 H6 B I2 N)'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        1512.0(11)
_cod_database_code               7132163
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.747
_shelx_estimated_absorpt_t_min   0.402
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N2-C13 \\sim N2-C12
 with sigma of 0.01
 C12-C11 \\sim C14-C13
 with sigma of 0.01
 C15-C14 \\sim C11-C10
 with sigma of 0.01
 C9-C10 \\sim C16-C15
 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22),
  C23(H23)
;
_shelx_res_checksum              79336
_shelx_hkl_checksum              2959
_olex2_submission_special_instructions 'No special instructions were received'