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

data_7132166
_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 H5 B I2 N2 O2'
_chemical_formula_sum            'C8 H5 B I2 N2 O2'
_chemical_formula_weight         425.75
_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
_audit_creation_date             2023-05-22
_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                82.588(3)
_cell_angle_beta                 89.880(3)
_cell_angle_gamma                85.833(3)
_cell_formula_units_Z            4
_cell_length_a                   7.8145(7)
_cell_length_b                   8.1585(7)
_cell_length_c                   17.1814(15)
_cell_measurement_reflns_used    8884
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.377
_cell_measurement_theta_min      2.614
_cell_volume                     1083.34(16)
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0531
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_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       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16757
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.397
_diffrn_reflns_theta_min         2.650
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.784
_exptl_absorpt_correction_T_max  0.2590
_exptl_absorpt_correction_T_min  0.1906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0901 before and 0.0644 after correction.
The Ratio of minimum to maximum transmission is 0.7359.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    2.610
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.591
_refine_diff_density_min         -0.788
_refine_diff_density_rms         0.187
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3980
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0110P)^2^+8.1145P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0762
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3261
_reflns_number_total             3980
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04359b2.cif
_cod_data_source_block           fang230328b_a
_cod_depositor_comments
;

2025-01-11
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C16 H10 B2 I4 N4 O4'
_cod_original_formula_weight         851.50
_cod_original_formula_moiety         '2(C8 H5 B I2 N2 O2)'
_cod_original_formula_units_Z            2
_cod_database_code               7132166
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.655
_shelx_estimated_absorpt_t_min   0.458
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15)
;
_shelx_res_checksum              59210
_shelx_hkl_checksum              52680
_olex2_submission_special_instructions 'No special instructions were received'