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#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/31/4033114.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4033114
loop_
_publ_author_name
'Zhang, Ying'
'Sun, Feiye'
'Dan, Wenyan'
'Fang, Xiangdong'
_publ_section_title
;
 Friedel-Crafts Acylation Reactions of BN-Substituted Arenes.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12877
_journal_page_last               12887
_journal_paper_doi               10.1021/acs.joc.7b02343
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C16 H19 B I N O'
_chemical_formula_weight         379.03
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 105.564(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.233(6)
_cell_length_b                   7.758(3)
_cell_length_c                   16.663(7)
_cell_measurement_reflns_used    9964
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      3.08
_cell_volume                     1647.9(12)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-III CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            48387
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_min         2.916
_exptl_absorpt_coefficient_mu    1.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_transmission_factor_max   1.0000
_exptl_transmission_factor_min   0.8019
_refine_diff_density_max         1.202
_refine_diff_density_min         -1.175
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3757
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0431P)²+2.1587P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0944
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3234
_reflns_number_total             3757
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b02343_si_002.cif
_cod_data_source_block           mo_160112a_compound_9f
_cod_depositor_comments
'Adding full bibliography for 4033111--4033119.cif.'
_cod_database_code               4033114
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.760
_shelx_estimated_absorpt_t_max   0.815
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
I1 I 0.89996(2) 0.29294(4) 0.69133(2) 0.05698(11) Uani 1 1 d . .
N1 N 0.58448(19) 0.4680(3) 0.70490(15) 0.0380(5) Uani 1 1 d . .
O1 O 0.5270(2) 0.1759(4) 0.44740(16) 0.0697(8) Uani 1 1 d . .
B1 B 0.6969(3) 0.4465(4) 0.73001(19) 0.0348(6) Uani 1 1 d . .
C1 C 0.7640(2) 0.5283(4) 0.81429(17) 0.0363(6) Uani 1 1 d . .
C2 C 0.7893(2) 0.4318(4) 0.88829(18) 0.0380(6) Uani 1 1 d . .
C3 C 0.8462(2) 0.5080(5) 0.96292(19) 0.0463(7) Uani 1 1 d . .
H3 H 0.8633 0.4423 1.0114 0.056 Uiso 1 1 calc R U
C4 C 0.8776(3) 0.6778(5) 0.9664(2) 0.0487(8) Uani 1 1 d . .
C5 C 0.8541(3) 0.7720(4) 0.8930(2) 0.0499(8) Uani 1 1 d . .
H5 H 0.8764 0.8860 0.8943 0.060 Uiso 1 1 calc R U
C6 C 0.7983(3) 0.7008(4) 0.8173(2) 0.0453(7) Uani 1 1 d . .
C7 C 0.7559(3) 0.2460(5) 0.8881(2) 0.0531(8) Uani 1 1 d . .
H7A H 0.6823 0.2407 0.8845 0.080 Uiso 1 1 calc R U
H7B H 0.7949 0.1912 0.9385 0.080 Uiso 1 1 calc R U
H7C H 0.7691 0.1879 0.8410 0.080 Uiso 1 1 calc R U
C8 C 0.9352(4) 0.7602(7) 1.0485(3) 0.0758(13) Uani 1 1 d . .
H8A H 0.9931 0.8268 1.0409 0.114 Uiso 1 1 calc R U
H8B H 0.9609 0.6719 1.0892 0.114 Uiso 1 1 calc R U
H8C H 0.8880 0.8341 1.0673 0.114 Uiso 1 1 calc R U
C9 C 0.7756(4) 0.8077(5) 0.7390(3) 0.0693(12) Uani 1 1 d . .
H9A H 0.7960 0.7449 0.6962 0.104 Uiso 1 1 calc R U
H9B H 0.8144 0.9135 0.7500 0.104 Uiso 1 1 calc R U
H9C H 0.7019 0.8328 0.7208 0.104 Uiso 1 1 calc R U
C10 C 0.7381(2) 0.3409(4) 0.66834(17) 0.0355(6) Uani 1 1 d . .
C11 C 0.6710(3) 0.2761(4) 0.59737(18) 0.0384(6) Uani 1 1 d . .
H11 H 0.6977 0.2119 0.5606 0.046 Uiso 1 1 calc R U
C12 C 0.5615(2) 0.3055(4) 0.57917(17) 0.0365(6) Uani 1 1 d . .
C13 C 0.5221(2) 0.4002(4) 0.63306(17) 0.0375(6) Uani 1 1 d . .
H13 H 0.4502 0.4191 0.6203 0.045 Uiso 1 1 calc R U
C14 C 0.5292(3) 0.5682(5) 0.7577(2) 0.0563(9) Uani 1 1 d . .
H14A H 0.5575 0.6828 0.7662 0.084 Uiso 1 1 calc R U
H14B H 0.5391 0.5120 0.8106 0.084 Uiso 1 1 calc R U
H14C H 0.4556 0.5740 0.7301 0.084 Uiso 1 1 calc R U
C15 C 0.4896(3) 0.2357(5) 0.5010(2) 0.0456(7) Uani 1 1 d . .
C16 C 0.3742(3) 0.2360(6) 0.4895(2) 0.0632(10) Uani 1 1 d . .
H16A H 0.3482 0.3518 0.4801 0.095 Uiso 1 1 calc R U
H16B H 0.3590 0.1906 0.5386 0.095 Uiso 1 1 calc R U
H16C H 0.3410 0.1657 0.4424 0.095 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C13 N1 B1 122.9(2)
C13 N1 C14 116.0(3)
B1 N1 C14 121.1(3)
N1 B1 C10 113.2(2)
N1 B1 C1 120.1(3)
C10 B1 C1 126.7(3)
C2 C1 C6 118.5(3)
C2 C1 B1 120.7(3)
C6 C1 B1 120.8(3)
C3 C2 C1 120.0(3)
C3 C2 C7 119.6(3)
C1 C2 C7 120.5(3)
C4 C3 C2 121.7(3)
C4 C3 H3 119.2
C2 C3 H3 119.2
C3 C4 C5 118.3(3)
C3 C4 C8 120.9(4)
C5 C4 C8 120.9(4)
C4 C5 C6 121.9(3)
C4 C5 H5 119.1
C6 C5 H5 119.1
C5 C6 C1 119.7(3)
C5 C6 C9 120.0(3)
C1 C6 C9 120.3(3)
C2 C7 H7A 109.5
C2 C7 H7B 109.5
H7A C7 H7B 109.5
C2 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C4 C8 H8A 109.5
C4 C8 H8B 109.5
H8A C8 H8B 109.5
C4 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C6 C9 H9A 109.5
C6 C9 H9B 109.5
H9A C9 H9B 109.5
C6 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C11 C10 B1 120.9(3)
C11 C10 I1 119.0(2)
B1 C10 I1 120.1(2)
C10 C11 C12 121.0(3)
C10 C11 H11 119.5
C12 C11 H11 119.5
C13 C12 C11 119.6(3)
C13 C12 C15 120.1(3)
C11 C12 C15 120.3(3)
N1 C13 C12 122.5(3)
N1 C13 H13 118.8
C12 C13 H13 118.8
N1 C14 H14A 109.5
N1 C14 H14B 109.5
H14A C14 H14B 109.5
N1 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
O1 C15 C16 120.6(3)
O1 C15 C12 119.1(3)
C16 C15 C12 120.2(3)
C15 C16 H16A 109.5
C15 C16 H16B 109.5
H16A C16 H16B 109.5
C15 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C10 2.105(3)
N1 C13 1.364(4)
N1 B1 1.443(4)
N1 C14 1.504(4)
O1 C15 1.222(5)
B1 C10 1.525(4)
B1 C1 1.579(4)
C1 C2 1.404(4)
C1 C6 1.409(4)
C2 C3 1.400(4)
C2 C7 1.508(5)
C3 C4 1.378(5)
C3 H3 0.9300
C4 C5 1.387(6)
C4 C8 1.517(5)
C5 C6 1.394(5)
C5 H5 0.9300
C6 C9 1.506(5)
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 C11 1.369(4)
C11 C12 1.417(4)
C11 H11 0.9300
C12 C13 1.367(4)
C12 C15 1.494(4)
C13 H13 0.9300
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C15 C16 1.486(5)
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C13 N1 B1 C10 -0.1(4)
C14 N1 B1 C10 179.9(3)
C13 N1 B1 C1 -179.8(3)
C14 N1 B1 C1 0.2(4)
N1 B1 C1 C2 93.4(4)
C10 B1 C1 C2 -86.3(4)
N1 B1 C1 C6 -85.4(4)
C10 B1 C1 C6 94.9(4)
C6 C1 C2 C3 0.7(4)
B1 C1 C2 C3 -178.1(3)
C6 C1 C2 C7 -179.1(3)
B1 C1 C2 C7 2.1(4)
C1 C2 C3 C4 0.8(5)
C7 C2 C3 C4 -179.3(3)
C2 C3 C4 C5 -2.0(5)
C2 C3 C4 C8 177.4(3)
C3 C4 C5 C6 1.5(5)
C8 C4 C5 C6 -177.8(4)
C4 C5 C6 C1 0.0(5)
C4 C5 C6 C9 -179.4(4)
C2 C1 C6 C5 -1.2(5)
B1 C1 C6 C5 177.7(3)
C2 C1 C6 C9 178.3(3)
B1 C1 C6 C9 -2.9(5)
N1 B1 C10 C11 -0.1(4)
C1 B1 C10 C11 179.6(3)
N1 B1 C10 I1 179.8(2)
C1 B1 C10 I1 -0.5(4)
B1 C10 C11 C12 0.1(5)
I1 C10 C11 C12 -179.8(2)
C10 C11 C12 C13 0.2(4)
C10 C11 C12 C15 179.3(3)
B1 N1 C13 C12 0.3(4)
C14 N1 C13 C12 -179.7(3)
C11 C12 C13 N1 -0.3(4)
C15 C12 C13 N1 -179.5(3)
C13 C12 C15 O1 168.3(3)
C11 C12 C15 O1 -10.8(5)
C13 C12 C15 C16 -12.9(5)
C11 C12 C15 C16 168.0(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139095662
