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#$Date: 2016-03-21 03:43:19 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178440 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/61/4026164.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_4026164
loop_
_publ_author_name
'Yuichi Hirano'
'Satoshi Kojima'
'Yohsuke Yamamoto'
_publ_contact_author             'Dr. Satoshi Kojima'
_publ_contact_author_email       skojima@sci.hiroshima-u.ac.jp
_publ_section_title
;
 A Hypervalent Pentacoordinate Boron Compound with an N-B-N Three-Center
 Four-Electron Bond
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2123
_journal_page_last               2131
_journal_paper_doi               10.1021/jo1024656
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C20 H20 B Cl N4 O2'
_chemical_formula_weight         394.66
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           36
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2c -2'
_symmetry_space_group_name_H-M   'C m c 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                   16.1669(9)
_cell_length_b                   9.9131(5)
_cell_length_c                   11.3102(6)
_cell_measurement_reflns_used    30
_cell_measurement_temperature    173
_cell_measurement_theta_max      26.135
_cell_measurement_theta_min      2.995
_cell_volume                     1812.62(17)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_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    SIR-97
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku SCXmini'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  Graphite
_diffrn_radiation_source         'long-fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9205
_diffrn_reflns_theta_full        27.32
_diffrn_reflns_theta_max         27.32
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 'ABSCOR (Higashi, 1995)'
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_description       plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2113
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0261
_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)+(0.0360P)²+0.7252P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0668
_reflns_number_gt                2047
_reflns_number_total             2113
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1024656_si_002.cif
_cod_data_source_block           yh768
_cod_database_code               4026164
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, 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'
'-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
C1 C 0.0000 0.21716(17) 0.03557(17) 0.0157(3) Uani 1 2 d S
C2 C 0.07463(8) 0.26935(14) -0.01056(12) 0.0175(3) Uani 1 1 d .
C3 C 0.07429(8) 0.36950(14) -0.09790(12) 0.0191(3) Uani 1 1 d .
H3 H 0.1249 0.4046 -0.1275 0.023 Uiso 1 1 calc R
C4 C 0.0000 0.41660(19) -0.14040(17) 0.0191(4) Uani 1 2 d S
C5 C 0.15650(9) 0.21483(13) 0.02685(13) 0.0176(3) Uani 1 1 d .
N1 N 0.15583(7) 0.11996(11) 0.11062(10) 0.0210(2) Uani 1 1 d .
C6 C 0.22952(9) 0.06678(14) 0.14122(13) 0.0218(3) Uani 1 1 d .
C7 C 0.30156(9) 0.10973(14) 0.08689(13) 0.0242(3) Uani 1 1 d .
H7 H 0.3534 0.0712 0.1074 0.029 Uiso 1 1 calc R
C8 C 0.29649(9) 0.21005(15) 0.00191(12) 0.0216(3) Uani 1 1 d .
N2 N 0.22329(7) 0.26365(12) -0.02853(10) 0.0206(3) Uani 1 1 d .
C9 C 0.23016(9) -0.03835(15) 0.23620(16) 0.0288(3) Uani 1 1 d .
H9 H 0.2239 0.0051 0.3135 0.043 Uiso 1 1 calc R
H9A H 0.2827 -0.0876 0.2338 0.043 Uiso 1 1 calc R
H9B H 0.1843 -0.1014 0.2235 0.043 Uiso 1 1 calc R
C10 C 0.37178(10) 0.26386(18) -0.05850(15) 0.0304(4) Uani 1 1 d .
H10 H 0.3614 0.2702 -0.1437 0.046 Uiso 1 1 calc R
H10A H 0.4185 0.2031 -0.0442 0.046 Uiso 1 1 calc R
H10B H 0.3848 0.3536 -0.0272 0.046 Uiso 1 1 calc R
Cl1 Cl 0.0000 0.53621(5) -0.25369(5) 0.02711(12) Uani 1 2 d S
B1 B 0.0000 0.0977(2) 0.12870(19) 0.0191(4) Uani 1 2 d S
O1 O 0.0000 0.11574(12) 0.24840(13) 0.0212(3) Uani 1 2 d S
C11 C 0.0000 -0.0161(2) 0.30134(19) 0.0260(4) Uani 1 2 d S
H11 H -0.0498 -0.0288 0.3511 0.031 Uiso 0.50 1 calc PR
H11A H 0.0498 -0.0288 0.3511 0.031 Uiso 0.50 1 calc PR
C12 C 0.0000 -0.1158(2) 0.19763(19) 0.0248(4) Uani 1 2 d S
H12 H 0.0498 -0.1739 0.2002 0.030 Uiso 0.50 1 calc PR
H12A H -0.0498 -0.1739 0.2002 0.030 Uiso 0.50 1 calc PR
O2 O 0.0000 -0.03450(12) 0.09293(11) 0.0202(3) Uani 1 2 d S
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 C2 117.32(17) 3 .
C2 C1 B1 121.27(8) 3 .
C2 C1 B1 121.27(8) . .
C3 C2 C1 121.12(12) . .
C3 C2 C5 117.42(11) . .
C1 C2 C5 121.38(13) . .
C4 C3 C2 119.38(12) . .
C4 C3 H3 120.3 . .
C2 C3 H3 120.3 . .
C3 C4 C3 121.68(18) . 3
C3 C4 Cl1 119.15(9) . .
C3 C4 Cl1 119.15(9) 3 .
N1 C5 N2 126.39(13) . .
N1 C5 C2 116.71(12) . .
N2 C5 C2 116.88(12) . .
C5 N1 C6 116.77(12) . .
N1 C6 C7 120.63(13) . .
N1 C6 C9 117.56(12) . .
C7 C6 C9 121.81(13) . .
C6 C7 C8 118.63(13) . .
C6 C7 H7 120.7 . .
C8 C7 H7 120.7 . .
N2 C8 C7 120.95(13) . .
N2 C8 C10 117.36(13) . .
C7 C8 C10 121.69(14) . .
C5 N2 C8 116.62(12) . .
C6 C9 H9 109.5 . .
C6 C9 H9A 109.5 . .
H9 C9 H9A 109.5 . .
C6 C9 H9B 109.5 . .
H9 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C8 C10 H10 109.5 . .
C8 C10 H10A 109.5 . .
H10 C10 H10A 109.5 . .
C8 C10 H10B 109.5 . .
H10 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
O1 B1 O2 114.69(17) . .
O1 B1 C1 124.11(17) . .
O2 B1 C1 121.20(17) . .
B1 O1 C11 107.08(16) . .
O1 C11 C12 105.51(16) . .
O1 C11 H11 110.6 . .
C12 C11 H11 110.6 . .
O1 C11 H11A 110.6 . .
C12 C11 H11A 110.6 . .
H11 C11 H11A 108.8 . .
O2 C12 C11 105.64(15) . .
O2 C12 H12 110.6 . .
C11 C12 H12 110.6 . .
O2 C12 H12A 110.6 . .
C11 C12 H12A 110.6 . .
H12 C12 H12A 108.7 . .
B1 O2 C12 107.09(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.4127(16) 3
C1 C2 1.4127(16) .
C1 B1 1.585(3) .
C2 C3 1.4006(18) .
C2 C5 1.4909(18) .
C3 C4 1.3754(16) .
C3 H3 0.9500 .
C4 C3 1.3754(16) 3
C4 Cl1 1.7458(19) .
C5 N1 1.3351(17) .
C5 N2 1.3388(19) .
N1 C6 1.3480(18) .
C6 C7 1.384(2) .
C6 C9 1.497(2) .
C7 C8 1.385(2) .
C7 H7 0.9500 .
C8 N2 1.3422(19) .
C8 C10 1.494(2) .
C9 H9 0.9800 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C10 H10 0.9800 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
B1 O1 1.366(3) .
B1 O2 1.371(2) .
O1 C11 1.438(2) .
C11 C12 1.534(3) .
C11 H11 0.9900 .
C11 H11A 0.9900 .
C12 O2 1.433(2) .
C12 H12 0.9900 .
C12 H12A 0.9900 .
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_1
_geom_torsion_site_symmetry_4
C2 C1 C2 C3 0.4(3) 3 .
B1 C1 C2 C3 176.24(14) . .
C2 C1 C2 C5 -176.13(10) 3 .
B1 C1 C2 C5 -0.3(2) . .
C1 C2 C3 C4 -0.8(2) . .
C5 C2 C3 C4 175.93(14) . .
C2 C3 C4 C3 1.1(3) . 3
C2 C3 C4 Cl1 -177.29(11) . .
C3 C2 C5 N1 179.65(12) . .
C1 C2 C5 N1 -3.65(19) . .
C3 C2 C5 N2 -1.73(18) . .
C1 C2 C5 N2 174.97(14) . .
N2 C5 N1 C6 -1.0(2) . .
C2 C5 N1 C6 177.46(12) . .
C5 N1 C6 C7 -0.2(2) . .
C5 N1 C6 C9 179.16(12) . .
N1 C6 C7 C8 1.1(2) . .
C9 C6 C7 C8 -178.27(13) . .
C6 C7 C8 N2 -0.8(2) . .
C6 C7 C8 C10 178.54(13) . .
N1 C5 N2 C8 1.2(2) . .
C2 C5 N2 C8 -177.22(11) . .
C7 C8 N2 C5 -0.26(19) . .
C10 C8 N2 C5 -179.66(13) . .
C2 C1 B1 O1 -92.18(15) 3 .
C2 C1 B1 O1 92.18(15) . .
C2 C1 B1 O2 87.82(15) 3 .
C2 C1 B1 O2 -87.82(15) . .
O2 B1 O1 C11 0.0 . .
C1 B1 O1 C11 180.0 . .
B1 O1 C11 C12 0.0 . .
O1 C11 C12 O2 0.0 . .
O1 B1 O2 C12 0.0 . .
C1 B1 O2 C12 180.0 . .
C11 C12 O2 B1 0.0 . .
