#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/67/1516746.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_1516746
loop_
_publ_author_name
'Yasuda, Makoto'
'Yoshioka, Sachiko'
'Yamasaki, Satoshi'
'Somyo, Toshio'
'Chiba, Kouji'
'Baba, Akio'
_publ_section_title
;
 Cage-shaped borate esters with enhanced Lewis acidity and catalytic
 activity.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              761
_journal_page_last               764
_journal_paper_doi               10.1021/ol053026+
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C24 H18 B N O3 '
_chemical_formula_sum            'C24 H18 B N O3'
_chemical_formula_weight         379.22
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.8638(6)
_cell_length_b                   15.4624(6)
_cell_length_c                   16.3768(6)
_cell_measurement_reflns_used    36289
_cell_measurement_temperature    277.2
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      1.3
_cell_volume                     3763.9(3)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 5.00
_diffrn_measured_fraction_theta_full 0.9998
_diffrn_measured_fraction_theta_max 0.9998
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.111
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            33660
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.52
_refine_diff_density_min         -0.47
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4303
_refine_ls_R_factor_gt           0.0677
_refine_ls_shift/su_max          0.0911
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.06000(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1602
_reflns_number_gt                1757
_reflns_number_total             4303
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ol053026%2Bsi20051227_043319.cif
_cod_data_source_block           5
_cod_original_cell_volume        3763.9(2)
_cod_original_formula_sum        'C24 H18 B N O3 '
_cod_database_code               1516746
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2+x,1/2-y,-z
-x,1/2+y,1/2-z
1/2-x,-y,1/2+z
-x,-y,-z
1/2-x,1/2+y,z
x,1/2-y,1/2+z
1/2+x,y,1/2-z
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_calc_flag
O(1) O 0.1854(2) 0.1414(1) 0.5957(1) 0.0381(7) Uani 1.00 d
O(2) O 0.0746(2) 0.1842(1) 0.6956(1) 0.0384(7) Uani 1.00 d
O(3) O 0.1808(2) 0.0695(1) 0.7272(1) 0.0365(7) Uani 1.00 d
N(1) N 0.0636(2) 0.0423(2) 0.6305(2) 0.0375(9) Uani 1.00 d
C(1) C 0.2757(2) 0.1554(2) 0.6043(2) 0.0341(10) Uani 1.00 d
C(2) C 0.3127(2) 0.1989(2) 0.6706(2) 0.0335(10) Uani 1.00 d
C(3) C 0.4063(3) 0.2057(2) 0.6721(3) 0.044(1) Uani 1.00 d
C(4) C 0.4607(3) 0.1734(3) 0.6118(3) 0.057(1) Uani 1.00 d
C(5) C 0.4224(3) 0.1338(3) 0.5447(3) 0.053(1) Uani 1.00 d
C(6) C 0.3308(3) 0.1256(2) 0.5416(3) 0.045(1) Uani 1.00 d
C(7) C 0.0974(2) 0.2696(2) 0.6866(2) 0.037(1) Uani 1.00 d
C(8) C 0.1829(2) 0.3000(2) 0.7069(2) 0.0324(10) Uani 1.00 d
C(9) C 0.1976(3) 0.3892(2) 0.7006(2) 0.042(1) Uani 1.00 d
C(10) C 0.1317(3) 0.4457(2) 0.6755(3) 0.049(1) Uani 1.00 d
C(11) C 0.0489(3) 0.4143(2) 0.6559(3) 0.049(1) Uani 1.00 d
C(12) C 0.0312(3) 0.3261(2) 0.6605(2) 0.044(1) Uani 1.00 d
C(13) C 0.1966(2) 0.1045(2) 0.8022(2) 0.0331(10) Uani 1.00 d
C(14) C 0.2336(2) 0.1872(2) 0.8100(2) 0.034(1) Uani 1.00 d
C(15) C 0.2452(3) 0.2188(2) 0.8892(2) 0.044(1) Uani 1.00 d
C(16) C 0.2233(3) 0.1712(3) 0.9570(3) 0.055(1) Uani 1.00 d
C(17) C 0.1887(3) 0.0887(3) 0.9481(2) 0.048(1) Uani 1.00 d
C(18) C 0.1768(3) 0.0552(2) 0.8711(2) 0.042(1) Uani 1.00 d
C(19) C 0.2590(2) 0.2436(2) 0.7378(2) 0.0328(10) Uani 1.00 d
C(20) C 0.0991(3) -0.0259(2) 0.5913(3) 0.052(1) Uani 1.00 d
C(21) C 0.0478(4) -0.0951(3) 0.5661(3) 0.060(2) Uani 1.00 d
C(22) C -0.0428(4) -0.0946(3) 0.5810(3) 0.067(2) Uani 1.00 d
C(23) C -0.0807(3) -0.0238(3) 0.6217(3) 0.067(2) Uani 1.00 d
C(24) C -0.0258(3) 0.0432(3) 0.6456(2) 0.051(1) Uani 1.00 d
B(1) B 0.1312(3) 0.1162(2) 0.6659(3) 0.035(1) Uani 1.00 d
H(1) H 0.431(2) 0.238(2) 0.717(2) 0.041(9) Uiso 1.00 calc
H(2) H 0.525(3) 0.177(2) 0.611(2) 0.063(9) Uiso 1.00 calc
H(3) H 0.464(3) 0.106(3) 0.498(3) 0.089(9) Uiso 1.00 calc
H(4) H 0.300(2) 0.098(2) 0.499(2) 0.046(9) Uiso 1.00 calc
H(5) H 0.253(2) 0.413(2) 0.714(2) 0.048(9) Uiso 1.00 calc
H(6) H 0.141(3) 0.509(2) 0.672(2) 0.059(9) Uiso 1.00 calc
H(7) H 0.002(2) 0.457(2) 0.633(2) 0.050(9) Uiso 1.00 calc
H(8) H -0.029(2) 0.304(2) 0.650(2) 0.019(7) Uiso 1.00 calc
H(9) H 0.266(2) 0.283(2) 0.891(2) 0.035(8) Uiso 1.00 calc
H(10) H 0.230(3) 0.191(2) 1.011(3) 0.064(9) Uiso 1.00 calc
H(11) H 0.162(2) 0.056(2) 1.002(2) 0.059(9) Uiso 1.00 calc
H(12) H 0.153(2) 0.001(2) 0.864(2) 0.015(7) Uiso 1.00 calc
H(13) H 0.302(2) 0.284(2) 0.758(2) 0.027(8) Uiso 1.00 calc
H(14) H 0.171(3) -0.022(2) 0.581(3) 0.082(8) Uiso 1.00 calc
H(15) H 0.084(3) -0.144(2) 0.535(2) 0.075(9) Uiso 1.00 calc
H(16) H -0.085(3) -0.142(3) 0.565(3) 0.083(9) Uiso 1.00 calc
H(17) H -0.158(4) -0.021(3) 0.638(3) 0.150(6) Uiso 1.00 calc
H(18) H -0.044(3) 0.099(3) 0.688(3) 0.093(8) Uiso 1.00 calc
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
N N 0.006 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
B B 0.001 0.001
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(1) O(1) B(1) 120.3(3) yes
C(7) O(2) B(1) 121.7(3) yes
C(13) O(3) B(1) 121.2(3) yes
C(20) N(1) C(24) 118.9(3) yes
C(20) N(1) B(1) 118.6(3) yes
C(24) N(1) B(1) 122.2(3) yes
O(1) C(1) C(2) 123.1(3) yes
O(1) C(1) C(6) 116.6(3) yes
C(2) C(1) C(6) 120.2(4) yes
C(1) C(2) C(3) 116.4(3) yes
C(1) C(2) C(19) 125.1(3) yes
C(3) C(2) C(19) 118.4(3) yes
C(2) C(3) C(4) 123.3(4) yes
C(3) C(4) C(5) 119.4(4) yes
C(4) C(5) C(6) 118.8(4) yes
C(1) C(6) C(5) 121.7(4) yes
O(2) C(7) C(8) 121.6(3) yes
O(2) C(7) C(12) 117.7(3) yes
C(8) C(7) C(12) 120.6(3) yes
C(7) C(8) C(9) 117.1(3) yes
C(7) C(8) C(19) 124.5(3) yes
C(9) C(8) C(19) 118.4(3) yes
C(8) C(9) C(10) 122.5(4) yes
C(9) C(10) C(11) 119.1(4) yes
C(10) C(11) C(12) 120.6(4) yes
C(7) C(12) C(11) 120.1(4) yes
O(3) C(13) C(14) 120.9(3) yes
O(3) C(13) C(18) 118.5(3) yes
C(14) C(13) C(18) 120.6(3) yes
C(13) C(14) C(15) 116.9(3) yes
C(13) C(14) C(19) 123.5(3) yes
C(15) C(14) C(19) 119.6(3) yes
C(14) C(15) C(16) 122.4(4) yes
C(15) C(16) C(17) 119.9(4) yes
C(16) C(17) C(18) 119.4(4) yes
C(13) C(18) C(17) 120.7(4) yes
C(2) C(19) C(8) 114.2(3) yes
C(2) C(19) C(14) 115.7(3) yes
C(8) C(19) C(14) 113.9(3) yes
N(1) C(20) C(21) 122.3(4) yes
C(20) C(21) C(22) 119.1(5) yes
C(21) C(22) C(23) 119.1(4) yes
C(22) C(23) C(24) 119.1(5) yes
N(1) C(24) C(23) 121.5(4) yes
O(1) B(1) O(2) 113.4(3) yes
O(1) B(1) O(3) 113.7(3) yes
O(1) B(1) N(1) 104.4(3) yes
O(2) B(1) O(3) 115.6(3) yes
O(2) B(1) N(1) 105.9(3) yes
O(3) B(1) N(1) 102.2(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(1) 1.366(4) yes
O(1) B(1) 1.457(5) yes
O(2) C(7) 1.371(4) yes
O(2) B(1) 1.431(4) yes
O(3) C(13) 1.362(4) yes
O(3) B(1) 1.441(4) yes
N(1) C(20) 1.343(5) yes
N(1) C(24) 1.352(5) yes
N(1) B(1) 1.630(4) yes
C(1) C(2) 1.391(5) yes
C(1) C(6) 1.393(5) yes
C(2) C(3) 1.395(5) yes
C(2) C(19) 1.525(5) yes
C(3) C(4) 1.371(6) yes
C(4) C(5) 1.381(6) yes
C(5) C(6) 1.369(6) yes
C(7) C(8) 1.395(5) yes
C(7) C(12) 1.384(5) yes
C(8) C(9) 1.401(4) yes
C(8) C(19) 1.515(4) yes
C(9) C(10) 1.375(5) yes
C(10) C(11) 1.362(6) yes
C(11) C(12) 1.390(5) yes
C(13) C(14) 1.399(4) yes
C(13) C(18) 1.392(5) yes
C(14) C(15) 1.397(5) yes
C(14) C(19) 1.516(4) yes
C(15) C(16) 1.370(5) yes
C(16) C(17) 1.383(6) yes
C(17) C(18) 1.376(5) yes
C(20) C(21) 1.378(6) yes
C(21) C(22) 1.369(6) yes
C(22) C(23) 1.400(7) yes
C(23) C(24) 1.376(6) yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
O(2) C(3) 3.326(5) 8_456
O(2) C(4) 3.584(6) 8_456
O(3) C(9) 3.351(4) 6_545
O(3) C(10) 3.485(5) 6_545
N(1) C(22) 3.570(5) 5_556
C(6) C(10) 3.586(5) 6_545
C(10) C(23) 3.438(6) 3_556
C(20) C(22) 3.483(6) 5_556
C(20) C(23) 3.582(6) 5_556
C(21) C(24) 3.575(6) 5_556
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_publ_flag
O(1) C(1) C(2) C(3) 178.0(3) yes
O(1) C(1) C(2) C(19) -5.8(5) yes
O(1) C(1) C(6) C(5) -178.2(3) yes
O(1) B(1) O(2) C(7) -28.3(5) yes
O(1) B(1) O(3) C(13) 112.7(3) yes
O(1) B(1) N(1) C(20) 53.7(4) yes
O(1) B(1) N(1) C(24) -132.5(3) yes
O(2) C(7) C(8) C(9) -175.9(3) yes
O(2) C(7) C(8) C(19) 2.0(5) yes
O(2) C(7) C(12) C(11) 175.4(3) yes
O(2) B(1) O(1) C(1) 106.6(3) yes
O(2) B(1) O(3) C(13) -21.0(4) yes
O(2) B(1) N(1) C(20) 173.6(3) yes
O(2) B(1) N(1) C(24) -12.6(5) yes
O(3) C(13) C(14) C(15) 178.3(3) yes
O(3) C(13) C(14) C(19) -0.2(5) yes
O(3) C(13) C(18) C(17) -177.9(3) yes
O(3) B(1) O(1) C(1) -28.2(4) yes
O(3) B(1) O(2) C(7) 105.4(4) yes
O(3) B(1) N(1) C(20) -64.9(4) yes
O(3) B(1) N(1) C(24) 108.8(4) yes
N(1) C(20) C(21) C(22) 0.4(7) yes
N(1) C(24) C(23) C(22) 0.3(7) yes
N(1) B(1) O(1) C(1) -138.7(3) yes
N(1) B(1) O(2) C(7) -142.2(3) yes
N(1) B(1) O(3) C(13) -135.5(3) yes
C(1) C(2) C(3) C(4) 1.2(5) yes
C(1) C(2) C(19) C(8) -46.5(4) yes
C(1) C(2) C(19) C(14) 88.7(4) yes
C(1) C(6) C(5) C(4) -0.4(6) yes
C(2) C(1) O(1) B(1) -41.4(4) yes
C(2) C(1) C(6) C(5) 3.3(6) yes
C(2) C(3) C(4) C(5) 1.7(6) yes
C(2) C(19) C(8) C(7) 83.9(4) yes
C(2) C(19) C(8) C(9) -98.3(4) yes
C(2) C(19) C(14) C(13) -46.9(5) yes
C(2) C(19) C(14) C(15) 134.6(4) yes
C(3) C(2) C(1) C(6) -3.6(5) yes
C(3) C(2) C(19) C(8) 129.6(3) yes
C(3) C(2) C(19) C(14) -95.2(4) yes
C(3) C(4) C(5) C(6) -2.1(6) yes
C(4) C(3) C(2) C(19) -175.3(3) yes
C(6) C(1) O(1) B(1) 140.1(3) yes
C(6) C(1) C(2) C(19) 172.6(3) yes
C(7) C(8) C(9) C(10) 0.0(6) yes
C(7) C(8) C(19) C(14) -52.1(5) yes
C(7) C(12) C(11) C(10) 1.2(6) yes
C(8) C(7) O(2) B(1) -48.3(5) yes
C(8) C(7) C(12) C(11) -1.2(6) yes
C(8) C(9) C(10) C(11) -0.1(6) yes
C(8) C(19) C(14) C(13) 88.4(4) yes
C(8) C(19) C(14) C(15) -90.1(4) yes
C(9) C(8) C(7) C(12) 0.7(5) yes
C(9) C(8) C(19) C(14) 125.7(3) yes
C(9) C(10) C(11) C(12) -0.5(6) yes
C(10) C(9) C(8) C(19) -178.0(4) yes
C(12) C(7) O(2) B(1) 135.0(4) yes
C(12) C(7) C(8) C(19) 178.5(3) yes
C(13) C(14) C(15) C(16) 1.2(5) yes
C(13) C(18) C(17) C(16) -1.9(6) yes
C(14) C(13) O(3) B(1) -51.3(4) yes
C(14) C(13) C(18) C(17) 3.4(5) yes
C(14) C(15) C(16) C(17) 0.3(6) yes
C(15) C(14) C(13) C(18) -3.0(5) yes
C(15) C(16) C(17) C(18) 0.0(6) yes
C(16) C(15) C(14) C(19) 179.8(4) yes
C(18) C(13) O(3) B(1) 130.1(3) yes
C(18) C(13) C(14) C(19) 178.4(3) yes
C(20) N(1) C(24) C(23) -0.2(6) yes
C(20) C(21) C(22) C(23) -0.3(7) yes
C(21) C(20) N(1) C(24) -0.1(6) yes
C(21) C(20) N(1) B(1) 173.8(4) yes
C(21) C(22) C(23) C(24) -0.1(7) yes
C(23) C(24) N(1) B(1) -173.9(4) yes
C(23) C(24) N(1) B(1) -173.9(4) yes
