#------------------------------------------------------------------------------
#$Date: 2019-11-07 23:56:44 +0200 (Thu, 07 Nov 2019) $
#$Revision: 224145 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/85/7048570.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_7048570
loop_
_publ_author_name
'Kitamoto, Yuichi'
'Kobayashi, Fumiaki'
'Suzuki, Takatsugu'
'Miyata, Yasuo'
'Kita, Hiroshi'
'Funaki, Kenji'
'Oi, Shuichi'
_publ_section_title
;
 Investigation of the Lewis acidic behaviour of an oxygen-bridged
 planarized triphenylborane toward amines and the properties of their
 Lewis acid-base adducts.
;
_journal_issue                   6
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2118
_journal_page_last               2127
_journal_paper_doi               10.1039/c8dt00128f
_journal_volume                  48
_journal_year                    2019
_chemical_formula_sum            'C22 H16 B Cl3 N O3'
_chemical_formula_weight         459.52
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-03-22 deposited with the CCDC.
2019-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 113.2150(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.783(3)
_cell_length_b                   9.9498(10)
_cell_length_c                   18.2611(19)
_cell_measurement_reflns_used    7359
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.90
_cell_measurement_theta_min      2.25
_cell_volume                     3971.4(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker APEXII'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material
'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayered confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11025
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.488
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6602
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1880
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.692
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4457
_refine_ls_number_restraints     106
_refine_ls_restrained_S_all      1.219
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0621P)²+8.6185P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1218
_reflns_number_gt                4106
_reflns_number_total             4457
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8dt00128f2.cif
_cod_data_source_block           kitamoto20160322
_cod_depositor_comments
'Adding full bibliography for 7048570--7048572.cif.'
_cod_original_cell_volume        3971.4(7)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7048570
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'
'-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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.35138(8) 0.25141(19) 0.09295(10) 0.0122(4) Uani 1 1 d . . .
C2 C 0.35657(8) 0.19025(19) 0.02737(11) 0.0133(4) Uani 1 1 d . . .
C3 C 0.33255(9) 0.0639(2) 0.00147(11) 0.0163(4) Uani 1 1 d . . .
H1 H 0.3383 0.0209 -0.0415 0.020 Uiso 1 1 calc R . .
C4 C 0.29953(9) 0.0016(2) 0.04083(12) 0.0187(4) Uani 1 1 d . . .
H2 H 0.2849 -0.0873 0.0261 0.022 Uiso 1 1 calc R . .
C5 C 0.28742(9) 0.0661(2) 0.10125(12) 0.0171(4) Uani 1 1 d . . .
H3 H 0.2626 0.0251 0.1250 0.021 Uiso 1 1 calc R . .
C6 C 0.31307(8) 0.19207(19) 0.12501(11) 0.0135(4) Uani 1 1 d . . .
C7 C 0.37723(8) 0.47095(19) 0.04349(11) 0.0121(3) Uani 1 1 d . . .
C8 C 0.36198(8) 0.60663(19) 0.03224(11) 0.0134(4) Uani 1 1 d . . .
C9 C 0.35849(9) 0.6744(2) -0.03606(12) 0.0173(4) Uani 1 1 d . . .
H4 H 0.3509 0.7684 -0.0417 0.021 Uiso 1 1 calc R . .
C10 C 0.36648(9) 0.6004(2) -0.09569(12) 0.0195(4) Uani 1 1 d . . .
H5 H 0.3654 0.6459 -0.1420 0.023 Uiso 1 1 calc R . .
C11 C 0.37604(9) 0.4612(2) -0.09016(12) 0.0185(4) Uani 1 1 d . . .
H6 H 0.3795 0.4116 -0.1326 0.022 Uiso 1 1 calc R . .
C12 C 0.38026(8) 0.39827(19) -0.02021(11) 0.0137(4) Uani 1 1 d . . .
C13 C 0.33124(8) 0.47183(19) 0.14708(10) 0.0121(3) Uani 1 1 d . . .
C14 C 0.29495(8) 0.40061(19) 0.17748(11) 0.0138(4) Uani 1 1 d . . .
C15 C 0.25447(9) 0.4653(2) 0.20366(11) 0.0180(4) Uani 1 1 d . . .
H7 H 0.2316 0.4165 0.2273 0.022 Uiso 1 1 calc R . .
C16 C 0.24866(9) 0.6041(2) 0.19402(12) 0.0195(4) Uani 1 1 d . . .
H8 H 0.2226 0.6506 0.2137 0.023 Uiso 1 1 calc R . .
C17 C 0.27967(9) 0.6773(2) 0.15646(11) 0.0176(4) Uani 1 1 d . . .
H9 H 0.2736 0.7714 0.1482 0.021 Uiso 1 1 calc R . .
C18 C 0.31967(8) 0.60812(19) 0.13145(11) 0.0139(4) Uani 1 1 d . . .
O1 O 0.29834(6) 0.26048(14) 0.18224(8) 0.0157(3) Uani 1 1 d . . .
O2 O 0.34788(6) 0.67856(14) 0.08872(8) 0.0152(3) Uani 1 1 d . . .
O3 O 0.38572(6) 0.25795(14) -0.01587(8) 0.0155(3) Uani 1 1 d . . .
N1 N 0.44617(7) 0.39411(15) 0.19214(9) 0.0098(3) Uani 1 1 d . . .
B1 B 0.37673(9) 0.3962(2) 0.11878(12) 0.0109(4) Uani 1 1 d . . .
C19 C 0.44550(9) 0.3236(2) 0.26413(12) 0.0225(5) Uani 1 1 d . . .
H10 H 0.4317 0.2297 0.2500 0.027 Uiso 1 1 calc R . .
H11 H 0.4160 0.3686 0.2819 0.027 Uiso 1 1 calc R . .
C20 C 0.49169(9) 0.3237(2) 0.16826(12) 0.0194(4) Uani 1 1 d . . .
H12 H 0.4940 0.3691 0.1213 0.023 Uiso 1 1 calc R . .
H13 H 0.4782 0.2299 0.1531 0.023 Uiso 1 1 calc R . .
C21 C 0.46867(9) 0.5339(2) 0.21634(13) 0.0218(4) Uani 1 1 d . . .
H14 H 0.4395 0.5821 0.2335 0.026 Uiso 1 1 calc R . .
H15 H 0.4706 0.5822 0.1700 0.026 Uiso 1 1 calc R . .
C22 C 0.44988(11) 0.0945(2) -0.12609(14) 0.0302(5) Uani 1 1 d DU . .
Cl1 Cl 0.43754(3) -0.06871(6) -0.10088(4) 0.03694(18) Uani 1 1 d DU A .
Cl2A Cl 0.40231(13) 0.0894(4) -0.23485(16) 0.0478(7) Uani 0.30 1 d PDU A 2
Cl3A Cl 0.52668(6) 0.1020(2) -0.12091(14) 0.0372(4) Uani 0.70 1 d PDU A 1
Cl3B Cl 0.5226(3) 0.1424(9) -0.1110(5) 0.068(3) Uani 0.20 1 d PDU A 2
Cl3C Cl 0.5068(4) 0.2066(9) -0.0887(6) 0.052(2) Uani 0.10 1 d PDU A 3
Cl2B Cl 0.39980(5) 0.15373(14) -0.21569(7) 0.0390(3) Uani 0.70 1 d PDU A 1
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'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 118.09(17) . .
C2 C1 B1 120.58(16) . .
C6 C1 B1 120.17(16) . .
C3 C2 C1 121.75(18) . .
C3 C2 O3 118.04(17) . .
C1 C2 O3 120.20(16) . .
C2 C3 C4 117.76(18) . .
C2 C3 H1 121.1 . .
C4 C3 H1 121.1 . .
C5 C4 C3 122.17(18) . .
C5 C4 H2 118.9 . .
C3 C4 H2 118.9 . .
C6 C5 C4 117.31(18) . .
C6 C5 H3 121.3 . .
C4 C5 H3 121.3 . .
C5 C6 C1 122.09(18) . .
C5 C6 O1 117.62(17) . .
C1 C6 O1 120.28(17) . .
C8 C7 C12 118.41(17) . .
C8 C7 B1 119.87(16) . .
C12 C7 B1 120.40(17) . .
C9 C8 C7 121.50(18) . .
C9 C8 O2 117.74(17) . .
C7 C8 O2 120.74(16) . .
C10 C9 C8 117.88(18) . .
C10 C9 H4 121.1 . .
C8 C9 H4 121.1 . .
C9 C10 C11 122.44(18) . .
C9 C10 H5 118.8 . .
C11 C10 H5 118.8 . .
C12 C11 C10 117.54(18) . .
C12 C11 H6 121.2 . .
C10 C11 H6 121.2 . .
C11 C12 C7 121.59(18) . .
C11 C12 O3 118.16(17) . .
C7 C12 O3 120.21(16) . .
C14 C13 C18 118.37(17) . .
C14 C13 B1 120.39(17) . .
C18 C13 B1 120.55(17) . .
C15 C14 C13 121.64(18) . .
C15 C14 O1 118.11(17) . .
C13 C14 O1 120.25(16) . .
C14 C15 C16 117.60(19) . .
C14 C15 H7 121.2 . .
C16 C15 H7 121.2 . .
C15 C16 C17 122.34(18) . .
C15 C16 H8 118.8 . .
C17 C16 H8 118.8 . .
C18 C17 C16 117.81(18) . .
C18 C17 H9 121.1 . .
C16 C17 H9 121.1 . .
C17 C18 C13 121.43(18) . .
C17 C18 O2 118.39(17) . .
C13 C18 O2 120.17(16) . .
C14 O1 C6 117.59(14) . .
C8 O2 C18 117.44(14) . .
C12 O3 C2 116.90(14) . .
C20 N1 C21 107.90(16) . .
C20 N1 C19 107.27(15) . .
C21 N1 C19 107.68(16) . .
C20 N1 B1 111.97(13) . .
C21 N1 B1 110.63(13) . .
C19 N1 B1 111.21(14) . .
C1 B1 C13 107.99(15) . .
C1 B1 C7 107.96(15) . .
C13 B1 C7 107.87(15) . .
C1 B1 N1 111.95(14) . .
C13 B1 N1 109.62(14) . .
C7 B1 N1 111.30(14) . .
N1 C19 C20 111.51(16) . 2_655
N1 C19 H10 109.3 . .
C20 C19 H10 109.3 2_655 .
N1 C19 H11 109.3 . .
C20 C19 H11 109.3 2_655 .
H10 C19 H11 108.0 . .
N1 C20 C19 110.95(15) . 2_655
N1 C20 H12 109.4 . .
C19 C20 H12 109.4 2_655 .
N1 C20 H13 109.4 . .
C19 C20 H13 109.4 2_655 .
H12 C20 H13 108.0 . .
N1 C21 C21 111.34(9) . 2_655
N1 C21 H14 109.4 . .
C21 C21 H14 109.4 2_655 .
N1 C21 H15 109.4 . .
C21 C21 H15 109.4 2_655 .
H14 C21 H15 108.0 . .
Cl3C C22 Cl2B 107.9(4) . .
Cl3C C22 Cl3B 31.3(4) . .
Cl2B C22 Cl3B 109.8(3) . .
Cl3C C22 Cl1 134.8(4) . .
Cl2B C22 Cl1 116.66(14) . .
Cl3B C22 Cl1 118.9(3) . .
Cl3C C22 Cl3A 46.3(4) . .
Cl2B C22 Cl3A 110.36(15) . .
Cl3B C22 Cl3A 15.1(3) . .
Cl1 C22 Cl3A 107.39(14) . .
Cl3C C22 Cl2A 120.4(4) . .
Cl2B C22 Cl2A 23.57(10) . .
Cl3B C22 Cl2A 109.3(3) . .
Cl1 C22 Cl2A 99.31(17) . .
Cl3A C22 Cl2A 103.64(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.392(3) .
C1 C6 1.394(3) .
C1 B1 1.561(3) .
C2 C3 1.385(3) .
C2 O3 1.410(2) .
C3 C4 1.401(3) .
C3 H1 0.9500 .
C4 C5 1.401(3) .
C4 H2 0.9500 .
C5 C6 1.387(3) .
C5 H3 0.9500 .
C6 O1 1.402(2) .
C7 C8 1.392(3) .
C7 C12 1.395(3) .
C7 B1 1.567(3) .
C8 C9 1.392(3) .
C8 O2 1.400(2) .
C9 C10 1.388(3) .
C9 H4 0.9500 .
C10 C11 1.401(3) .
C10 H5 0.9500 .
C11 C12 1.390(3) .
C11 H6 0.9500 .
C12 O3 1.401(2) .
C13 C14 1.390(3) .
C13 C18 1.391(3) .
C13 B1 1.564(3) .
C14 C15 1.390(3) .
C14 O1 1.397(2) .
C15 C16 1.393(3) .
C15 H7 0.9500 .
C16 C17 1.394(3) .
C16 H8 0.9500 .
C17 C18 1.389(3) .
C17 H9 0.9500 .
C18 O2 1.401(2) .
N1 C20 1.492(2) .
N1 C21 1.493(2) .
N1 C19 1.496(2) .
N1 B1 1.667(2) .
C19 C20 1.517(3) 2_655
C19 H10 0.9900 .
C19 H11 0.9900 .
C20 C19 1.517(3) 2_655
C20 H12 0.9900 .
C20 H13 0.9900 .
C21 C21 1.513(4) 2_655
C21 H14 0.9900 .
C21 H15 0.9900 .
C22 Cl3C 1.677(6) .
C22 Cl2B 1.705(2) .
C22 Cl3B 1.708(6) .
C22 Cl1 1.744(2) .
C22 Cl3A 1.793(3) .
C22 Cl2A 1.859(3) .
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
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 -9.9(3) .
B1 C1 C2 C3 -177.66(16) .
C6 C1 C2 O3 168.70(16) .
B1 C1 C2 O3 0.9(3) .
C1 C2 C3 C4 3.5(3) .
O3 C2 C3 C4 -175.13(16) .
C2 C3 C4 C5 3.8(3) .
C3 C4 C5 C6 -4.3(3) .
C4 C5 C6 C1 -2.5(3) .
C4 C5 C6 O1 176.47(16) .
C2 C1 C6 C5 9.4(3) .
B1 C1 C6 C5 177.19(17) .
C2 C1 C6 O1 -169.52(16) .
B1 C1 C6 O1 -1.7(3) .
C12 C7 C8 C9 -9.3(3) .
B1 C7 C8 C9 -176.25(17) .
C12 C7 C8 O2 168.82(16) .
B1 C7 C8 O2 1.9(3) .
C7 C8 C9 C10 4.5(3) .
O2 C8 C9 C10 -173.74(17) .
C8 C9 C10 C11 1.8(3) .
C9 C10 C11 C12 -3.0(3) .
C10 C11 C12 C7 -2.1(3) .
C10 C11 C12 O3 175.81(17) .
C8 C7 C12 C11 8.1(3) .
B1 C7 C12 C11 174.98(17) .
C8 C7 C12 O3 -169.77(16) .
B1 C7 C12 O3 -2.9(3) .
C18 C13 C14 C15 -10.0(3) .
B1 C13 C14 C15 179.48(17) .
C18 C13 C14 O1 169.86(16) .
B1 C13 C14 O1 -0.7(3) .
C13 C14 C15 C16 3.8(3) .
O1 C14 C15 C16 -176.05(17) .
C14 C15 C16 C17 2.8(3) .
C15 C16 C17 C18 -3.0(3) .
C16 C17 C18 C13 -3.5(3) .
C16 C17 C18 O2 175.61(16) .
C14 C13 C18 C17 9.8(3) .
B1 C13 C18 C17 -179.64(17) .
C14 C13 C18 O2 -169.31(16) .
B1 C13 C18 O2 1.2(3) .
C15 C14 O1 C6 149.42(17) .
C13 C14 O1 C6 -30.4(2) .
C5 C6 O1 C14 -147.24(17) .
C1 C6 O1 C14 31.7(2) .
C9 C8 O2 C18 146.48(17) .
C7 C8 O2 C18 -31.7(2) .
C17 C18 O2 C8 -149.12(17) .
C13 C18 O2 C8 30.0(2) .
C11 C12 O3 C2 -144.81(17) .
C7 C12 O3 C2 33.2(2) .
C3 C2 O3 C12 146.44(17) .
C1 C2 O3 C12 -32.2(2) .
C2 C1 B1 C13 142.03(17) .
C6 C1 B1 C13 -25.5(2) .
C2 C1 B1 C7 25.6(2) .
C6 C1 B1 C7 -141.86(17) .
C2 C1 B1 N1 -97.20(19) .
C6 C1 B1 N1 95.29(19) .
C14 C13 B1 C1 26.8(2) .
C18 C13 B1 C1 -143.58(16) .
C14 C13 B1 C7 143.21(16) .
C18 C13 B1 C7 -27.1(2) .
C14 C13 B1 N1 -95.44(19) .
C18 C13 B1 N1 94.21(19) .
C8 C7 B1 C1 141.96(17) .
C12 C7 B1 C1 -24.7(2) .
C8 C7 B1 C13 25.5(2) .
C12 C7 B1 C13 -141.17(17) .
C8 C7 B1 N1 -94.80(19) .
C12 C7 B1 N1 98.53(19) .
C20 N1 B1 C1 60.5(2) .
C21 N1 B1 C1 -179.08(16) .
C19 N1 B1 C1 -59.5(2) .
C20 N1 B1 C13 -179.67(16) .
C21 N1 B1 C13 -59.3(2) .
C19 N1 B1 C13 60.3(2) .
C20 N1 B1 C7 -60.4(2) .
C21 N1 B1 C7 60.0(2) .
C19 N1 B1 C7 179.60(16) .
C20 N1 C19 C20 58.4(2) 2_655
C21 N1 C19 C20 -57.5(2) 2_655
B1 N1 C19 C20 -178.89(17) 2_655
C21 N1 C20 C19 57.8(2) 2_655
C19 N1 C20 C19 -57.94(19) 2_655
B1 N1 C20 C19 179.79(17) 2_655
C20 N1 C21 C21 -58.0(3) 2_655
C19 N1 C21 C21 57.5(3) 2_655
B1 N1 C21 C21 179.2(2) 2_655
