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#$Date: 2025-08-20 17:59:05 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301833 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/40/4114005.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_4114005
loop_
_publ_author_name
'Cory A. Jaska'
'Karen Temple'
'Alan J. Lough'
'Ian Manners'
_publ_section_title
;
 Transition Metal-Catalyzed Formation of Boron-Nitrogen Bonds: Catalytic
 Dehydrocoupling of Amine-Borane Adducts to Form Aminoboranes and
 Borazines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9424
_journal_page_last               9434
_journal_paper_doi               10.1021/ja030160l
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C18 H18 B3 N3'
_chemical_formula_weight         308.78
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7831(2)
_cell_length_b                   19.9186(3)
_cell_length_c                   10.9654(7)
_cell_measurement_reflns_used    1684
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.6
_cell_volume                     1699.95(12)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2002)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SHELXTL V6.12 (Sheldrick, 2001)'
_computing_publication_material  'SHELXTL V6.12 (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXTL V6.12 (Sheldrick, 2001)'
_computing_structure_solution    'SHELXTL V6.12 (Sheldrick, 2001)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1572
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         2.81
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.111
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       0.024(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         1572
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0291
_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)+(0.0409P)²+0.1397P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0719
_reflns_number_gt                1481
_reflns_number_total             1572
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja030160l_2.cif
_cod_data_source_block           k01197a
_cod_database_code               4114005
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, 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
N3 N 0.28556(18) 0.11091(7) 0.67596(14) 0.0280(3) Uani 1 1 d .
N2 N 0.25384(17) 0.23431(7) 0.67761(14) 0.0283(4) Uani 1 1 d .
N1 N 0.21881(18) 0.17177(7) 0.48560(13) 0.0273(3) Uani 1 1 d .
C13 C 0.3237(2) 0.04865(8) 0.73766(17) 0.0282(4) Uani 1 1 d .
B2 B 0.2839(3) 0.17271(10) 0.7423(2) 0.0290(5) Uani 1 1 d .
C1 C 0.1782(2) 0.17031(8) 0.35703(17) 0.0265(4) Uani 1 1 d .
C8 C 0.3360(2) 0.35294(9) 0.69592(19) 0.0362(4) Uani 1 1 d .
H8A H 0.3919 0.3503 0.6191 0.043 Uiso 1 1 calc R
C12 C 0.1730(3) 0.30167(10) 0.85599(18) 0.0366(4) Uani 1 1 d .
H12A H 0.1154 0.2638 0.8891 0.044 Uiso 1 1 calc R
C7 C 0.2543(2) 0.29674(9) 0.74361(17) 0.0291(4) Uani 1 1 d .
C15 C 0.4683(3) -0.05836(9) 0.7423(2) 0.0412(5) Uani 1 1 d .
H15A H 0.5411 -0.0904 0.7043 0.049 Uiso 1 1 calc R
B1 B 0.2193(3) 0.23435(10) 0.54938(19) 0.0290(5) Uani 1 1 d .
B3 B 0.2496(3) 0.10994(11) 0.54790(19) 0.0279(4) Uani 1 1 d .
C18 C 0.2545(2) 0.03529(10) 0.85212(18) 0.0347(4) Uani 1 1 d .
H18A H 0.1808 0.0670 0.8902 0.042 Uiso 1 1 calc R
C9 C 0.3360(3) 0.41273(10) 0.7602(2) 0.0451(5) Uani 1 1 d .
H9A H 0.3914 0.4510 0.7268 0.054 Uiso 1 1 calc R
C5 C 0.0159(3) 0.12379(10) 0.19039(18) 0.0389(5) Uani 1 1 d .
H5A H -0.0676 0.0929 0.1613 0.047 Uiso 1 1 calc R
C11 C 0.1756(3) 0.36181(11) 0.9201(2) 0.0481(6) Uani 1 1 d .
H11A H 0.1214 0.3647 0.9976 0.058 Uiso 1 1 calc R
C17 C 0.2940(3) -0.02484(11) 0.91049(19) 0.0414(5) Uani 1 1 d .
H17A H 0.2475 -0.0338 0.9889 0.050 Uiso 1 1 calc R
C16 C 0.4000(3) -0.07158(10) 0.8557(2) 0.0439(5) Uani 1 1 d .
H16A H 0.4257 -0.1126 0.8960 0.053 Uiso 1 1 calc R
C14 C 0.4309(2) 0.00164(9) 0.68343(19) 0.0344(4) Uani 1 1 d .
H14A H 0.4790 0.0105 0.6055 0.041 Uiso 1 1 calc R
C3 C 0.2191(3) 0.21102(11) 0.15291(19) 0.0387(5) Uani 1 1 d .
H3A H 0.2755 0.2404 0.0975 0.046 Uiso 1 1 calc R
C6 C 0.0562(2) 0.12572(9) 0.31340(17) 0.0334(4) Uani 1 1 d .
H6A H -0.0003 0.0962 0.3683 0.040 Uiso 1 1 calc R
C4 C 0.0969(3) 0.16665(10) 0.11015(17) 0.0388(5) Uani 1 1 d .
H4A H 0.0687 0.1657 0.0259 0.047 Uiso 1 1 calc R
C10 C 0.2563(3) 0.41721(11) 0.8720(2) 0.0500(6) Uani 1 1 d .
H10A H 0.2571 0.4584 0.9157 0.060 Uiso 1 1 calc R
C2 C 0.2606(2) 0.21321(10) 0.27590(18) 0.0323(4) Uani 1 1 d .
H2A H 0.3448 0.2439 0.3045 0.039 Uiso 1 1 calc R
H1B H 0.188(2) 0.2840(9) 0.5021(18) 0.030(5) Uiso 1 1 d .
H2B H 0.309(3) 0.1731(9) 0.838(2) 0.033(5) Uiso 1 1 d .
H3B H 0.241(2) 0.0613(10) 0.4977(18) 0.033(5) 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 '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
B2 N3 B3 120.59(16)
B2 N3 C13 120.18(15)
B3 N3 C13 119.23(15)
B1 N2 B2 121.09(16)
B1 N2 C7 119.61(15)
B2 N2 C7 119.29(14)
B3 N1 B1 121.16(15)
B3 N1 C1 119.06(15)
B1 N1 C1 119.71(15)
C14 C13 C18 119.33(17)
C14 C13 N3 120.15(16)
C18 C13 N3 120.52(16)
N3 B2 N2 119.02(17)
C6 C1 C2 119.28(17)
C6 C1 N1 119.98(16)
C2 C1 N1 120.75(16)
C9 C8 C7 120.1(2)
C7 C12 C11 120.2(2)
C12 C7 C8 119.04(18)
C12 C7 N2 120.41(16)
C8 C7 N2 120.54(17)
C16 C15 C14 120.22(19)
N1 B1 N2 118.73(17)
N1 B3 N3 119.34(17)
C13 C18 C17 119.59(18)
C10 C9 C8 120.6(2)
C4 C5 C6 120.05(18)
C10 C11 C12 120.3(2)
C16 C17 C18 120.8(2)
C15 C16 C17 119.60(18)
C13 C14 C15 120.48(19)
C4 C3 C2 120.70(19)
C1 C6 C5 120.61(18)
C5 C4 C3 119.64(18)
C11 C10 C9 119.71(19)
C3 C2 C1 119.71(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N3 B2 1.430(3)
N3 B3 1.432(3)
N3 C13 1.443(2)
N2 B1 1.432(3)
N2 B2 1.437(2)
N2 C7 1.439(2)
N1 B3 1.429(3)
N1 B1 1.429(2)
N1 C1 1.445(2)
C13 C14 1.388(3)
C13 C18 1.391(3)
C1 C6 1.385(3)
C1 C2 1.390(3)
C8 C9 1.384(3)
C8 C7 1.389(3)
C12 C7 1.389(3)
C12 C11 1.389(3)
C15 C16 1.377(3)
C15 C14 1.389(3)
C18 C17 1.392(3)
C9 C10 1.377(3)
C5 C4 1.378(3)
C5 C6 1.385(3)
C11 C10 1.375(4)
C17 C16 1.382(3)
C3 C4 1.381(3)
C3 C2 1.387(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 545565
2 PubChem 628132
