#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/76/4117675.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_4117675
loop_
_publ_author_name
'Zhiguo Zhou'
'Atsushi Wakamiya'
'Tomokatsu Kushida'
'Shigehiro Yamaguchi'
_publ_section_title
;
 Planarized Triarylboranes: Stabilization by Structural Constraint and
 Their Plane-to-Bowl Conversion
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4529
_journal_page_last               4532
_journal_paper_doi               10.1021/ja211944q
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C25 H21 B O'
_chemical_formula_weight         348.23
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 92.182(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.223(2)
_cell_length_b                   9.4772(16)
_cell_length_c                   15.291(3)
_cell_measurement_reflns_used    2829
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.5050
_cell_measurement_theta_min      2.0143
_cell_volume                     1770.0(5)
_computing_molecular_graphics    'ORTEP 3 for windows'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APAX '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0600
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8981
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_correction_T_min  0.9848
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3297
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0449
_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/[?²(Fo²)+(0.0250P)²+0.0060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0854
_reflns_number_gt                2136
_reflns_number_total             3297
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja211944q_si_002_3.cif
_cod_data_source_block           compd6
_cod_original_cell_volume        1770.1(5)
_cod_database_code               4117675
loop_
_publ_contact_author_name
_publ_contact_author_address
_publ_contact_author_email
_publ_contact_author_fax
_publ_contact_author_phone
' Atsushi Wakamiya '
; 
    Institute for Chemical Research, Kyoto Unversity, and JST-PRESTO,
  Uji, Kyoto 611-0011, Japan 
;
' wakamiya@chem.nagoya-u.ac.jp' ' +81-774-38-3173 ' ' +81-774-38-3178 '
' Shigehiro Yamaguchi '
; 
    Department of Chemistry, Graduate School of Science, Nagoya University, 
    Furo, Chikusa, Nagoya 464-8602, Japan
;
' yamaguchi@chem.nagoya-u.ac.jp' ' +81-52-789-2291 ' ' +81-52-789-5947 '
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
B1 B 0.94135(15) 0.0418(2) 0.66038(13) 0.0190(5) Uani 1 1 d .
C1 C 0.99854(13) 0.02931(17) 0.74899(11) 0.0178(4) Uani 1 1 d .
C2 C 0.96308(13) -0.07300(17) 0.80901(11) 0.0190(4) Uani 1 1 d .
C3 C 1.01684(13) -0.08234(18) 0.88997(11) 0.0211(4) Uani 1 1 d .
H1 H 0.9953 -0.1517 0.9308 0.025 Uiso 1 1 calc R
C4 C 1.10206(13) 0.00917(18) 0.91182(12) 0.0223(4) Uani 1 1 d .
H2 H 1.1384 0.0013 0.9676 0.027 Uiso 1 1 calc R
C5 C 1.13537(13) 0.11174(18) 0.85413(12) 0.0223(4) Uani 1 1 d .
H3 H 1.1925 0.1751 0.8712 0.027 Uiso 1 1 calc R
C6 C 1.08546(13) 0.12214(17) 0.77136(11) 0.0186(4) Uani 1 1 d .
C7 C 0.97915(13) 0.14965(17) 0.59466(11) 0.0179(4) Uani 1 1 d .
C8 C 1.06833(13) 0.23773(18) 0.61672(11) 0.0196(4) Uani 1 1 d .
C9 C 1.10210(14) 0.33327(18) 0.55313(12) 0.0236(4) Uani 1 1 d .
H4 H 1.1624 0.3938 0.5663 0.028 Uiso 1 1 calc R
C10 C 1.04940(14) 0.34111(18) 0.47175(12) 0.0242(4) Uani 1 1 d .
H5 H 1.0750 0.4054 0.4295 0.029 Uiso 1 1 calc R
C11 C 0.95953(14) 0.25623(18) 0.45089(12) 0.0234(4) Uani 1 1 d .
H6 H 0.9227 0.2634 0.3952 0.028 Uiso 1 1 calc R
C12 C 0.92444(13) 0.16079(17) 0.51260(11) 0.0193(4) Uani 1 1 d .
C13 C 0.84153(13) -0.05028(17) 0.63795(11) 0.0193(4) Uani 1 1 d .
C14 C 0.78566(13) -0.03334(18) 0.55672(12) 0.0210(4) Uani 1 1 d .
C15 C 0.69312(14) -0.11373(19) 0.53576(12) 0.0256(5) Uani 1 1 d .
H7 H 0.6543 -0.1013 0.4813 0.031 Uiso 1 1 calc R
C16 C 0.65852(14) -0.21238(19) 0.59585(12) 0.0272(5) Uani 1 1 d .
H8 H 0.5956 -0.2682 0.5821 0.033 Uiso 1 1 calc R
C17 C 0.71412(14) -0.23049(19) 0.67520(12) 0.0260(5) Uani 1 1 d .
H9 H 0.6891 -0.2994 0.7149 0.031 Uiso 1 1 calc R
C18 C 0.80639(13) -0.14996(18) 0.69866(11) 0.0204(4) Uani 1 1 d .
C19 C 0.86579(13) -0.17313(18) 0.78781(11) 0.0210(4) Uani 1 1 d .
C20 C 0.90967(14) -0.32615(18) 0.78999(12) 0.0281(5) Uani 1 1 d .
H10 H 0.9636 -0.3379 0.7447 0.042 Uiso 1 1 calc R
H11 H 0.8489 -0.3920 0.7791 0.042 Uiso 1 1 calc R
H12 H 0.9444 -0.3456 0.8476 0.042 Uiso 1 1 calc R
C21 C 0.78129(13) -0.15448(19) 0.85994(12) 0.0269(5) Uani 1 1 d .
H13 H 0.8148 -0.1815 0.9167 0.040 Uiso 1 1 calc R
H14 H 0.7175 -0.2146 0.8467 0.040 Uiso 1 1 calc R
H15 H 0.7581 -0.0556 0.8620 0.040 Uiso 1 1 calc R
C22 C 1.12256(13) 0.23884(17) 0.70855(11) 0.0202(4) Uani 1 1 d .
C23 C 1.24849(13) 0.22930(19) 0.70204(12) 0.0259(5) Uani 1 1 d .
H16 H 1.2681 0.1372 0.6781 0.039 Uiso 1 1 calc R
H17 H 1.2833 0.2405 0.7604 0.039 Uiso 1 1 calc R
H18 H 1.2738 0.3042 0.6635 0.039 Uiso 1 1 calc R
C24 C 1.09232(14) 0.38231(17) 0.74994(12) 0.0272(5) Uani 1 1 d .
H19 H 1.1191 0.4594 0.7138 0.041 Uiso 1 1 calc R
H20 H 1.1261 0.3889 0.8090 0.041 Uiso 1 1 calc R
H21 H 1.0126 0.3893 0.7532 0.041 Uiso 1 1 calc R
C25 C 0.82452(14) 0.07256(18) 0.49146(12) 0.0218(4) Uani 1 1 d .
O1 O 0.77448(10) 0.08756(13) 0.42116(8) 0.0309(3) Uani 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'
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
C1 B1 C7 120.40(16)
C1 B1 C13 119.78(17)
C7 B1 C13 119.77(17)
C6 C1 C2 121.10(16)
C6 C1 B1 119.25(16)
C2 C1 B1 119.64(16)
C3 C2 C1 118.56(16)
C3 C2 C19 118.95(16)
C1 C2 C19 122.48(15)
C2 C3 C4 120.20(17)
C5 C4 C3 121.48(17)
C4 C5 C6 120.09(16)
C5 C6 C1 118.53(16)
C5 C6 C22 119.27(15)
C1 C6 C22 122.13(15)
C8 C7 C12 120.63(16)
C8 C7 B1 119.64(16)
C12 C7 B1 119.73(16)
C7 C8 C9 117.62(16)
C7 C8 C22 122.01(15)
C9 C8 C22 120.22(16)
C10 C9 C8 121.33(17)
C9 C10 C11 120.90(17)
C12 C11 C10 118.94(17)
C11 C12 C7 120.55(16)
C11 C12 C25 119.05(16)
C7 C12 C25 120.37(16)
C14 C13 C18 120.77(16)
C14 C13 B1 119.38(16)
C18 C13 B1 119.85(16)
C15 C14 C13 120.34(17)
C15 C14 C25 119.14(16)
C13 C14 C25 120.52(16)
C16 C15 C14 118.81(17)
C17 C16 C15 120.94(17)
C16 C17 C18 121.60(17)
C17 C18 C13 117.53(17)
C17 C18 C19 119.97(16)
C13 C18 C19 122.50(15)
C18 C19 C20 107.77(14)
C18 C19 C2 115.61(14)
C20 C19 C2 107.93(14)
C18 C19 C21 108.06(14)
C20 C19 C21 109.37(14)
C2 C19 C21 108.00(13)
C8 C22 C6 116.02(14)
C8 C22 C23 109.73(14)
C6 C22 C23 108.31(13)
C8 C22 C24 106.20(14)
C6 C22 C24 107.09(14)
C23 C22 C24 109.29(14)
O1 C25 C12 119.88(16)
O1 C25 C14 119.98(16)
C12 C25 C14 120.14(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
B1 C1 1.506(3)
B1 C7 1.518(2)
B1 C13 1.528(2)
C1 C6 1.411(2)
C1 C2 1.414(2)
C2 C3 1.382(2)
C2 C19 1.546(2)
C3 C4 1.386(2)
C4 C5 1.384(2)
C5 C6 1.387(2)
C6 C22 1.544(2)
C7 C8 1.404(2)
C7 C12 1.403(2)
C8 C9 1.402(2)
C8 C22 1.530(2)
C9 C10 1.381(2)
C10 C11 1.389(2)
C11 C12 1.387(2)
C12 C25 1.505(2)
C13 C14 1.404(2)
C13 C18 1.403(2)
C14 C15 1.391(2)
C14 C25 1.505(2)
C15 C16 1.388(2)
C16 C17 1.379(2)
C17 C18 1.397(2)
C18 C19 1.536(2)
C19 C20 1.546(2)
C19 C21 1.550(2)
C22 C23 1.549(2)
C22 C24 1.550(2)
C25 O1 1.2247(19)
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
C7 B1 C1 C6 2.0(2)
C13 B1 C1 C6 -175.27(14)
C7 B1 C1 C2 -179.22(14)
C13 B1 C1 C2 3.5(2)
C6 C1 C2 C3 -1.2(2)
B1 C1 C2 C3 -179.97(15)
C6 C1 C2 C19 177.99(14)
B1 C1 C2 C19 -0.7(2)
C1 C2 C3 C4 1.3(2)
C19 C2 C3 C4 -177.90(14)
C2 C3 C4 C5 0.2(2)
C3 C4 C5 C6 -1.9(3)
C4 C5 C6 C1 2.0(2)
C4 C5 C6 C22 179.01(15)
C2 C1 C6 C5 -0.4(2)
B1 C1 C6 C5 178.31(15)
C2 C1 C6 C22 -177.37(15)
B1 C1 C6 C22 1.4(2)
C1 B1 C7 C8 0.3(2)
C13 B1 C7 C8 177.60(15)
C1 B1 C7 C12 -179.47(15)
C13 B1 C7 C12 -2.2(2)
C12 C7 C8 C9 -1.8(2)
B1 C7 C8 C9 178.39(15)
C12 C7 C8 C22 173.75(15)
B1 C7 C8 C22 -6.0(2)
C7 C8 C9 C10 0.3(2)
C22 C8 C9 C10 -175.41(15)
C8 C9 C10 C11 1.3(3)
C9 C10 C11 C12 -1.3(2)
C10 C11 C12 C7 -0.3(2)
C10 C11 C12 C25 177.71(15)
C8 C7 C12 C11 1.9(2)
B1 C7 C12 C11 -178.34(15)
C8 C7 C12 C25 -176.10(14)
B1 C7 C12 C25 3.7(2)
C1 B1 C13 C14 177.05(15)
C7 B1 C13 C14 -0.3(2)
C1 B1 C13 C18 -2.6(2)
C7 B1 C13 C18 -179.92(15)
C18 C13 C14 C15 1.1(2)
B1 C13 C14 C15 -178.52(15)
C18 C13 C14 C25 -179.29(15)
B1 C13 C14 C25 1.1(2)
C13 C14 C15 C16 -1.2(2)
C25 C14 C15 C16 179.24(15)
C14 C15 C16 C17 0.3(3)
C15 C16 C17 C18 0.6(3)
C16 C17 C18 C13 -0.7(2)
C16 C17 C18 C19 179.82(16)
C14 C13 C18 C17 -0.2(2)
B1 C13 C18 C17 179.44(15)
C14 C13 C18 C19 179.30(15)
B1 C13 C18 C19 -1.0(2)
C17 C18 C19 C20 62.31(19)
C13 C18 C19 C20 -117.19(17)
C17 C18 C19 C2 -176.89(14)
C13 C18 C19 C2 3.6(2)
C17 C18 C19 C21 -55.8(2)
C13 C18 C19 C21 124.72(16)
C3 C2 C19 C18 176.53(15)
C1 C2 C19 C18 -2.7(2)
C3 C2 C19 C20 -62.76(19)
C1 C2 C19 C20 118.02(17)
C3 C2 C19 C21 55.4(2)
C1 C2 C19 C21 -123.83(17)
C7 C8 C22 C6 9.0(2)
C9 C8 C22 C6 -175.53(14)
C7 C8 C22 C23 132.12(16)
C9 C8 C22 C23 -52.4(2)
C7 C8 C22 C24 -109.86(17)
C9 C8 C22 C24 65.62(19)
C5 C6 C22 C8 176.50(15)
C1 C6 C22 C8 -6.6(2)
C5 C6 C22 C23 52.6(2)
C1 C6 C22 C23 -130.46(16)
C5 C6 C22 C24 -65.14(19)
C1 C6 C22 C24 111.77(17)
C11 C12 C25 O1 -1.3(2)
C7 C12 C25 O1 176.74(16)
C11 C12 C25 C14 179.09(15)
C7 C12 C25 C14 -2.9(2)
C15 C14 C25 O1 0.4(2)
C13 C14 C25 O1 -179.21(16)
C15 C14 C25 C12 180.00(15)
C13 C14 C25 C12 0.4(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660604
