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#$Date: 2025-08-21 14:21:36 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301847 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/01/58/7015836.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_7015836
loop_
_publ_author_name
'Barnes, Stephanie S.'
'Vogels, Christopher M.'
'Decken, Andreas'
'Westcott, Stephen A.'
_publ_section_title
;
 Addition of boranes to N-aryl-salicylaldimines: intramolecular
 hydrogenation of imines.
;
_journal_issue                   17
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4707
_journal_page_last               4714
_journal_paper_doi               10.1039/c1dt10132c
_journal_volume                  40
_journal_year                    2011
_chemical_formula_moiety         'C21 H18 B N O3'
_chemical_formula_sum            'C21 H18 B N O3'
_chemical_formula_weight         343.17
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.931(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.124(6)
_cell_length_b                   7.653(3)
_cell_length_c                   14.192(5)
_cell_measurement_reflns_used    5733
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      28.2325
_cell_measurement_theta_min      2.5575
_cell_volume                     1730.0(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker AXS SMART1000/P4'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11611
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.28
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              K760
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9935
_exptl_absorpt_correction_T_min  0.9537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Shard
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3860
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0380
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0403P)²+0.4779P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.1045
_reflns_number_gt                2745
_reflns_number_total             3860
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c1dt10132c.txt
_cod_data_source_block           sw080138
_cod_original_sg_symbol_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7015836
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.19127(11) 0.6572(2) 0.72747(11) 0.0293(4) Uani 1 1 d . . .
N1 N 0.22712(7) 0.63038(16) 0.62891(8) 0.0250(3) Uani 1 1 d . . .
O1 O 0.12841(7) 0.52547(15) 0.73503(7) 0.0378(3) Uani 1 1 d . . .
O2 O 0.15753(6) 0.83568(14) 0.72776(7) 0.0327(3) Uani 1 1 d . . .
O3 O 0.26084(6) 0.64885(13) 0.80632(7) 0.0298(3) Uani 1 1 d . . .
C1 C 0.08866(9) 0.4329(2) 0.66124(10) 0.0301(3) Uani 1 1 d . . .
C2 C 0.01998(10) 0.3303(2) 0.67418(12) 0.0382(4) Uani 1 1 d . . .
C3 C -0.01974(11) 0.2313(2) 0.59981(13) 0.0395(4) Uani 1 1 d . . .
C4 C 0.00725(10) 0.2304(2) 0.51081(13) 0.0363(4) Uani 1 1 d . . .
C5 C 0.07507(10) 0.3309(2) 0.49744(11) 0.0312(3) Uani 1 1 d . . .
C6 C 0.11696(9) 0.4329(2) 0.57236(10) 0.0267(3) Uani 1 1 d . . .
C7 C 0.18972(9) 0.53301(19) 0.56104(10) 0.0254(3) Uani 1 1 d . . .
C8 C 0.30539(9) 0.71846(19) 0.61825(9) 0.0251(3) Uani 1 1 d . . .
C9 C 0.30334(9) 0.8870(2) 0.58090(10) 0.0288(3) Uani 1 1 d . . .
C10 C 0.38061(11) 0.9673(2) 0.57667(12) 0.0374(4) Uani 1 1 d . . .
C11 C 0.45530(11) 0.8833(3) 0.60815(12) 0.0427(4) Uani 1 1 d . . .
C12 C 0.45499(10) 0.7141(3) 0.64328(11) 0.0385(4) Uani 1 1 d . . .
C13 C 0.37999(9) 0.6278(2) 0.64830(10) 0.0300(3) Uani 1 1 d . . .
C14 C 0.22309(11) 0.9799(3) 0.54245(13) 0.0372(4) Uani 1 1 d . . .
C15 C 0.37990(12) 0.4416(2) 0.68273(13) 0.0391(4) Uani 1 1 d . . .
C16 C 0.21509(10) 0.9290(2) 0.78843(10) 0.0304(3) Uani 1 1 d . . .
C21 C 0.21764(12) 1.1062(2) 0.80423(12) 0.0400(4) Uani 1 1 d . . .
C20 C 0.28515(13) 1.1720(3) 0.86778(12) 0.0455(5) Uani 1 1 d . . .
C19 C 0.34652(12) 1.0625(3) 0.91316(12) 0.0433(4) Uani 1 1 d . . .
C18 C 0.34381(10) 0.8817(2) 0.89707(11) 0.0349(4) Uani 1 1 d . . .
C17 C 0.27698(9) 0.8184(2) 0.83461(10) 0.0287(3) Uani 1 1 d . . .
H21 H 0.1740(12) 1.179(3) 0.7713(13) 0.049(5) Uiso 1 1 d . . .
H18 H 0.3870(10) 0.802(2) 0.9283(12) 0.037(5) Uiso 1 1 d . . .
H20 H 0.2900(12) 1.299(3) 0.8798(13) 0.055(6) Uiso 1 1 d . . .
H19 H 0.3929(11) 1.115(2) 0.9566(13) 0.046(5) Uiso 1 1 d . . .
H5 H 0.0963(10) 0.333(2) 0.4361(13) 0.041(5) Uiso 1 1 d . . .
H4 H -0.0216(11) 0.160(2) 0.4598(12) 0.041(5) Uiso 1 1 d . . .
H3 H -0.0664(11) 0.161(2) 0.6097(12) 0.040(5) Uiso 1 1 d . . .
H2 H 0.0014(11) 0.332(2) 0.7370(13) 0.047(5) Uiso 1 1 d . . .
H7 H 0.2133(9) 0.5248(19) 0.5011(11) 0.026(4) Uiso 1 1 d . . .
H12 H 0.5069(12) 0.655(2) 0.6631(12) 0.045(5) Uiso 1 1 d . . .
H10 H 0.3803(11) 1.086(3) 0.5501(13) 0.047(5) Uiso 1 1 d . . .
H11 H 0.5100(12) 0.938(3) 0.6068(13) 0.053(5) Uiso 1 1 d . . .
H14A H 0.1764(14) 0.950(3) 0.5737(16) 0.073(7) Uiso 1 1 d . . .
H14B H 0.2046(14) 0.958(3) 0.4731(18) 0.083(7) Uiso 1 1 d . . .
H14C H 0.2319(15) 1.105(4) 0.5463(18) 0.096(9) Uiso 1 1 d . . .
H15A H 0.3602(12) 0.436(3) 0.7427(14) 0.056(6) Uiso 1 1 d . . .
H15B H 0.4361(13) 0.394(3) 0.6917(14) 0.060(6) Uiso 1 1 d . . .
H15C H 0.3427(13) 0.361(3) 0.6346(14) 0.060(6) Uiso 1 1 d . . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 B1 O3 112.17(13) . . ?
O1 B1 O2 112.56(13) . . ?
O3 B1 O2 106.22(13) . . ?
O1 B1 N1 109.07(12) . . ?
O3 B1 N1 108.95(12) . . ?
O2 B1 N1 107.71(12) . . ?
C7 N1 C8 120.04(12) . . ?
C7 N1 B1 122.25(12) . . ?
C8 N1 B1 117.70(11) . . ?
C1 O1 B1 124.45(12) . . ?
C16 O2 B1 105.80(12) . . ?
C17 O3 B1 105.77(12) . . ?
O1 C1 C2 119.20(14) . . ?
O1 C1 C6 121.18(13) . . ?
C2 C1 C6 119.57(14) . . ?
C3 C2 C1 119.66(15) . . ?
C3 C2 H2 122.2(11) . . ?
C1 C2 H2 118.1(11) . . ?
C2 C3 C4 121.56(16) . . ?
C2 C3 H3 118.9(10) . . ?
C4 C3 H3 119.5(10) . . ?
C5 C4 C3 119.19(16) . . ?
C5 C4 H4 120.7(11) . . ?
C3 C4 H4 120.1(11) . . ?
C4 C5 C6 120.40(15) . . ?
C4 C5 H5 121.6(10) . . ?
C6 C5 H5 118.0(10) . . ?
C5 C6 C1 119.61(14) . . ?
C5 C6 C7 121.25(13) . . ?
C1 C6 C7 119.11(13) . . ?
N1 C7 C6 121.43(13) . . ?
N1 C7 H7 118.9(9) . . ?
C6 C7 H7 119.7(9) . . ?
C9 C8 C13 122.99(14) . . ?
C9 C8 N1 119.83(13) . . ?
C13 C8 N1 117.17(13) . . ?
C8 C9 C10 117.03(14) . . ?
C8 C9 C14 122.99(14) . . ?
C10 C9 C14 119.94(15) . . ?
C11 C10 C9 121.40(16) . . ?
C11 C10 H10 120.5(11) . . ?
C9 C10 H10 118.1(11) . . ?
C10 C11 C12 120.02(16) . . ?
C10 C11 H11 122.5(11) . . ?
C12 C11 H11 117.5(11) . . ?
C11 C12 C13 120.91(16) . . ?
C11 C12 H12 119.8(11) . . ?
C13 C12 H12 119.2(11) . . ?
C12 C13 C8 117.60(15) . . ?
C12 C13 C15 120.73(15) . . ?
C8 C13 C15 121.65(14) . . ?
C9 C14 H14A 114.5(13) . . ?
C9 C14 H14B 112.8(13) . . ?
H14A C14 H14B 106.2(18) . . ?
C9 C14 H14C 109.7(15) . . ?
H14A C14 H14C 109(2) . . ?
H14B C14 H14C 104.0(19) . . ?
C13 C15 H15A 110.5(12) . . ?
C13 C15 H15B 110.6(12) . . ?
H15A C15 H15B 107.5(16) . . ?
C13 C15 H15C 112.4(11) . . ?
H15A C15 H15C 108.6(16) . . ?
H15B C15 H15C 107.1(16) . . ?
O2 C16 C21 128.27(15) . . ?
O2 C16 C17 110.22(14) . . ?
C21 C16 C17 121.49(15) . . ?
C16 C21 C20 117.51(17) . . ?
C16 C21 H21 119.5(12) . . ?
C20 C21 H21 123.0(11) . . ?
C19 C20 C21 120.97(18) . . ?
C19 C20 H20 119.1(11) . . ?
C21 C20 H20 120.0(11) . . ?
C20 C19 C18 121.47(18) . . ?
C20 C19 H19 117.7(11) . . ?
C18 C19 H19 120.8(11) . . ?
C17 C18 C19 117.07(17) . . ?
C17 C18 H18 120.3(10) . . ?
C19 C18 H18 122.6(10) . . ?
O3 C17 C18 128.12(15) . . ?
O3 C17 C16 110.37(13) . . ?
C18 C17 C16 121.49(15) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 O1 1.445(2) . ?
B1 O3 1.458(2) . ?
B1 O2 1.471(2) . ?
B1 N1 1.6074(19) . ?
N1 C7 1.2907(18) . ?
N1 C8 1.4592(18) . ?
O1 C1 1.3419(19) . ?
O2 C16 1.3657(19) . ?
O3 C17 1.3711(19) . ?
C1 C2 1.393(2) . ?
C1 C6 1.406(2) . ?
C2 C3 1.374(2) . ?
C2 H2 0.983(19) . ?
C3 C4 1.398(2) . ?
C3 H3 0.956(18) . ?
C4 C5 1.374(2) . ?
C4 H4 0.961(17) . ?
C5 C6 1.405(2) . ?
C5 H5 0.983(18) . ?
C6 C7 1.431(2) . ?
C7 H7 0.986(15) . ?
C8 C9 1.393(2) . ?
C8 C13 1.397(2) . ?
C9 C10 1.399(2) . ?
C9 C14 1.503(2) . ?
C10 C11 1.377(3) . ?
C10 H10 0.984(19) . ?
C11 C12 1.388(3) . ?
C11 H11 0.98(2) . ?
C12 C13 1.390(2) . ?
C12 H12 0.956(18) . ?
C13 C15 1.507(2) . ?
C14 H14A 0.96(2) . ?
C14 H14B 1.00(3) . ?
C14 H14C 0.97(3) . ?
C15 H15A 0.95(2) . ?
C15 H15B 0.97(2) . ?
C15 H15C 1.04(2) . ?
C16 C21 1.374(2) . ?
C16 C17 1.393(2) . ?
C21 C20 1.395(3) . ?
C21 H21 0.960(19) . ?
C20 C19 1.378(3) . ?
C20 H20 0.99(2) . ?
C19 C18 1.402(3) . ?
C19 H19 0.979(18) . ?
C18 C17 1.373(2) . ?
C18 H18 0.978(17) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139156572
