Metal Nitrate Mediated Regioselective Nitration of BN-Substituted Arenes
Zhang, Ying; Dan, Wenyan; Fang, Xiangdong; Organometallics 36 (2017) 1677–; doi:10.1021/acs.organomet.7b00120

data_4089265
_publ_section_title
;
 Metal Nitrate Mediated Regioselective Nitration of BN-Substituted Arenes
;
_journal_issue                   9
_journal_name_full               Organometallics
_journal_page_first              1677
_journal_paper_doi               10.1021/acs.organomet.7b00120
_journal_volume                  36
_journal_year                    2017
_chemical_formula_sum            'C14 H17 B N2 O2'
_chemical_formula_weight         256.10
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.4174(13)
_cell_length_b                   15.627(4)
_cell_length_c                   21.286(5)
_cell_measurement_reflns_used    9972
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      68.28
_cell_measurement_theta_min      3.50
_cell_volume                     2799.9(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-III CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            22641
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.533
_diffrn_reflns_theta_min         3.509
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.150
_exptl_transmission_factor_max   0.7531
_exptl_transmission_factor_min   0.6114
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
; 
 Flack x determined using 1911 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.04(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         5147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0550P)^2^+0.5108P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.0986
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                4783
_reflns_number_total             5147
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om7b00120_si_002.cif
_cod_data_source_block           cu_20151228a
_cod_original_cell_volume        2799.8(10)
_cod_database_code               4089265
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.855
_shelx_estimated_absorpt_t_max   0.909
_shelx_res_checksum              71248
_shelx_hkl_checksum              89518