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

data_7132165
_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 Br2 N2 O2'
_chemical_formula_sum            'C8 H5 B Br2 N2 O2'
_chemical_formula_weight         331.77
_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             2021-04-13
_audit_creation_method
;
FinalCif V85 by Daniel Kratzert, Freiburg 2021,
https://github.com/dkratzert/FinalCif
;
_audit_update_record
;
2023-08-23 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                98.209(4)
_cell_angle_beta                 97.619(4)
_cell_angle_gamma                98.727(4)
_cell_formula_units_Z            6
_cell_length_a                   10.6162(12)
_cell_length_b                   10.7945(11)
_cell_length_c                   13.7859(16)
_cell_measurement_reflns_used    6992
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      25.26
_cell_measurement_theta_min      2.65
_cell_volume                     1526.2(3)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      190.0
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_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       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15784
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.351
_diffrn_reflns_theta_min         2.647
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.944
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5135
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1130 before and 0.0572 after correction.
The Ratio of minimum to maximum transmission is 0.6891.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.166
_exptl_crystal_description       block
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.748
_refine_diff_density_min         -0.823
_refine_diff_density_rms         0.142
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     802
_refine_ls_number_reflns         5532
_refine_ls_number_restraints     1467
_refine_ls_restrained_S_all      0.930
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0581
_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^)+(0.0858P)^2^+11.2837P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1562
_refine_ls_wR_factor_ref         0.1685
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4474
_reflns_number_total             5532
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04359b2.cif
_cod_data_source_block           210322b_a
_cod_database_code               7132165
_shelx_shelxl_version_number     2018/3
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_estimated_absorpt_t_min   0.382
_shelx_estimated_absorpt_t_max   0.504
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.8629(14)
 0.1371(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 N4A-O4A
 1.24 with sigma of 0.01
 C10-C11 \\sim C10-C9
 with sigma of 0.01
 C14-N4 \\sim C11A-N4A
 with sigma of 0.01
 C22-N6 \\sim C19A-N6A
 with sigma of 0.02
 C6-N2 \\sim C3A-N2A
 with sigma of 0.01
 N4A-O3A \\sim N4A-O4A \\sim N4-O3 \\sim N4-O4
 with sigma of 0.006
 N6A-O5A \\sim N6A-O6A
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.02 and sigma
for terminal atoms of 0.04 within 2A
Uanis(Br1A) \\sim Ueq: with sigma of 0.006 and sigma for terminal atoms of 0.012
Uanis(Br4A) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.006
Uanis(O6) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(N6A) \\sim Ueq, Uanis(O3A) \\sim Ueq, Uanis(O4A) \\sim Ueq, Uanis(O2A)
\\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.006
Uanis(O1A) \\sim Ueq: with sigma of 0.006 and sigma for terminal atoms of 0.012
5. Same fragment restrains
{C9, C10, C11, C12, B2, N3, C13, C14, C15, C16, Br3, Br4} sigma for 1-2: 0.02,
1-3: 0.04
as in
{C9A, C10A, C11A, C12A, B2A, N3A, C13A, C14A, C15A, C16A, Br3A, Br4A}
{C17, C18, C19, C20, B3, N5, C21, C22, C23, C24, Br5, Br6} sigma for 1-2: 0.02,
1-3: 0.04
as in
{C17A, C18A, C19A, C20A, B3A, N5A, C21A, C22A, C23A, C24A, Br5A, Br6A}
{C1, C2, C3, C4, B1, N1, C5, C6, C7, C8, Br1, Br2} sigma for 1-2: 0.02, 1-3:
0.04
as in
{C1A, C2A, C3A, C4A, B1A, N1A, C5A, C6A, C7A, C8A, Br1A, Br2A}
6. Others
 Sof(C1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(C4A)=Sof(H4A)=Sof(B1A)=Sof(N1A)=
 Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(Br1A)=
 Sof(Br2A)=Sof(N2A)=Sof(O1A)=Sof(O2A)=1-FVAR(1)
 Sof(C1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4)=Sof(B1)=Sof(N1)=
 Sof(C5)=Sof(H5)=Sof(C6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(Br1)=Sof(Br2)=Sof(N2)=
 Sof(O1)=Sof(O2)=FVAR(1)
 Sof(C17A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(C20A)=Sof(H20A)=Sof(B3A)=Sof(N5A)=
 Sof(C21A)=Sof(H21A)=Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(H23A)=Sof(C24A)=
 Sof(Br5A)=Sof(Br6A)=Sof(N6A)=Sof(O5A)=Sof(O6A)=1-FVAR(2)
 Sof(C17)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=Sof(C20)=Sof(H20)=Sof(B3)=
 Sof(N5)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(C23)=Sof(H23)=Sof(C24)=Sof(Br5)=
 Sof(Br6)=Sof(N6)=Sof(O5)=Sof(O6)=FVAR(2)
 Sof(C9A)=Sof(C10A)=Sof(H10A)=Sof(C11A)=Sof(C12A)=Sof(H12A)=Sof(B2A)=Sof(N3A)=
 Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=
 Sof(Br3A)=Sof(Br4A)=Sof(N4A)=Sof(O3A)=Sof(O4A)=1-FVAR(3)
 Sof(C9)=Sof(C10)=Sof(H10)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12)=Sof(B2)=Sof(N3)=
 Sof(C13)=Sof(H13)=Sof(C14)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(Br3)=Sof(Br4)=
 Sof(N4)=Sof(O3)=Sof(O4)=FVAR(3)
7.a Free rotating group:
 N6A(O5A,O6A)
7.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C10A(H10A), C12A(H12A),
 C13A(H13A), C14A(H14A), C15A(H15A), C18(H18), C19(H19), C20(H20), C21(H21),
 C23(H23), C18A(H18A), C20A(H20A), C21A(H21A), C22A(H22A), C23A(H23A), C2(H2),
 C3(H3), C4(H4), C5(H5), C7(H7), C2A(H2A), C4A(H4A), C5A(H5A), C6A(H6A),
 C7A(H7A)
;
_shelx_res_checksum              17288
_shelx_hkl_checksum              5760