#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:58:25 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178708 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/19/4081967.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_4081967
loop_
_publ_author_name
'Xie, Liang'
'Zhang, Jianying'
'Hu, Hongfan'
'Cui, Chunming'
_publ_section_title
;
 Synthesis and Reactions of π-Conjugated Iminoboranes Stabilized by
 Intramolecular Imine Groups
;
_journal_issue                   23
_journal_name_full               Organometallics
_journal_page_first              6875
_journal_paper_doi               10.1021/om4008407
_journal_volume                  32
_journal_year                    2013
_chemical_formula_moiety         'C27 H37 B N2'
_chemical_formula_sum            'C27 H37 B N2'
_chemical_formula_weight         400.40
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                   19.302(5)
_cell_length_b                   11.162(3)
_cell_length_c                   11.311(3)
_cell_measurement_reflns_used    8457
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      1.8
_cell_volume                     2436.9(11)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r2'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r2'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.6
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn 724CCD camera'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  Multilayer
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24065
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         2.09
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  0.9889
_exptl_absorpt_correction_T_min  0.9864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Crystalclear
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.091
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         3048
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0456
_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)+(0.0625P)²+0.3589P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1213
_reflns_number_gt                2722
_reflns_number_total             3048
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om4008407_si_002.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        2437.0(10)
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               4081967
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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
B1 B 0.07310(8) 0.2500 0.12037(14) 0.0209(3) Uani 1 2 d S
N1 N 0.14248(6) 0.2500 0.12324(10) 0.0239(3) Uani 1 2 d S
N2 N 0.03363(6) 0.2500 0.24164(10) 0.0208(3) Uani 1 2 d S
C1 C 0.18849(7) 0.2500 0.02974(12) 0.0240(3) Uani 1 2 d S
C2 C 0.21335(5) 0.14059(10) -0.01668(9) 0.0284(3) Uani 1 1 d .
C3 C 0.25678(5) 0.14274(13) -0.11510(10) 0.0360(3) Uani 1 1 d .
H3 H 0.2725 0.0693 -0.1481 0.043 Uiso 1 1 calc R
C4 C 0.27748(8) 0.2500 -0.16564(14) 0.0408(5) Uani 1 2 d S
H4 H 0.3057 0.2500 -0.2345 0.049 Uiso 1 2 calc SR
C5 C 0.19126(6) 0.02436(11) 0.03845(11) 0.0351(3) Uani 1 1 d .
H5A H 0.1415 0.0126 0.0258 0.053 Uiso 1 1 calc R
H5B H 0.2009 0.0264 0.1235 0.053 Uiso 1 1 calc R
H5C H 0.2169 -0.0418 0.0021 0.053 Uiso 1 1 calc R
C6 C 0.07145(7) 0.2500 0.35198(12) 0.0219(3) Uani 1 2 d S
C7 C 0.09174(5) 0.14052(10) 0.40016(9) 0.0264(2) Uani 1 1 d .
C8 C 0.13157(6) 0.14271(11) 0.50277(10) 0.0344(3) Uani 1 1 d .
H8 H 0.1455 0.0694 0.5381 0.041 Uiso 1 1 calc R
C9 C 0.15109(9) 0.2500 0.55405(14) 0.0399(4) Uani 1 2 d S
H9 H 0.1779 0.2500 0.6245 0.048 Uiso 1 2 calc SR
C10 C 0.07052(6) 0.02436(10) 0.34384(11) 0.0339(3) Uani 1 1 d .
H10A H 0.0209 0.0110 0.3570 0.051 Uiso 1 1 calc R
H10B H 0.0970 -0.0415 0.3790 0.051 Uiso 1 1 calc R
H10C H 0.0798 0.0278 0.2587 0.051 Uiso 1 1 calc R
C11 C 0.00994(7) 0.2500 0.02935(12) 0.0211(3) Uani 1 2 d S
C12 C -0.04781(7) 0.2500 0.09631(13) 0.0237(3) Uani 1 2 d S
H12 H -0.0933 0.2500 0.0642 0.028 Uiso 1 2 calc SR
C13 C -0.03344(7) 0.2500 0.22347(12) 0.0219(3) Uani 1 2 d S
C14 C 0.01013(7) 0.2500 -0.10455(12) 0.0223(3) Uani 1 2 d S
C15 C -0.06353(7) 0.2500 -0.15550(13) 0.0255(3) Uani 1 2 d S
H15A H -0.0612 0.2500 -0.2421 0.038 Uiso 1 2 calc SR
H15B H -0.0882 0.3217 -0.1285 0.038 Uiso 0.50 1 calc PR
H15C H -0.0882 0.1783 -0.1285 0.038 Uiso 0.50 1 calc PR
C16 C 0.04807(5) 0.13835(10) -0.14947(9) 0.0283(3) Uani 1 1 d .
H16A H 0.0961 0.1394 -0.1211 0.042 Uiso 1 1 calc R
H16B H 0.0477 0.1378 -0.2361 0.042 Uiso 1 1 calc R
H16C H 0.0247 0.0664 -0.1199 0.042 Uiso 1 1 calc R
C17 C -0.09288(7) 0.2500 0.31090(13) 0.0263(3) Uani 1 2 d S
C18 C -0.13702(6) 0.13799(11) 0.28549(11) 0.0364(3) Uani 1 1 d .
H18A H -0.1533 0.1403 0.2035 0.055 Uiso 1 1 calc R
H18B H -0.1769 0.1365 0.3390 0.055 Uiso 1 1 calc R
H18C H -0.1089 0.0660 0.2978 0.055 Uiso 1 1 calc R
C19 C -0.07244(8) 0.2500 0.44129(14) 0.0365(4) Uani 1 2 d S
H19A H -0.1143 0.2500 0.4903 0.055 Uiso 1 2 calc SR
H19B H -0.0449 0.3217 0.4586 0.055 Uiso 0.50 1 calc PR
H19C H -0.0449 0.1783 0.4586 0.055 Uiso 0.50 1 calc PR
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'
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
N1 B1 N2 117.65(12) . .
N1 B1 C11 141.21(13) . .
N2 B1 C11 101.14(11) . .
B1 N1 C1 128.63(12) . .
C13 N2 C6 129.34(12) . .
C13 N2 B1 110.02(11) . .
C6 N2 B1 120.64(11) . .
N1 C1 C2 120.19(7) . .
N1 C1 C2 120.19(7) . 7_565
C2 C1 C2 119.57(13) . 7_565
C3 C2 C1 119.08(11) . .
C3 C2 C5 121.16(11) . .
C1 C2 C5 119.74(10) . .
C4 C3 C2 121.18(12) . .
C4 C3 H3 119.4 . .
C2 C3 H3 119.4 . .
C3 C4 C3 119.56(15) . 7_565
C3 C4 H4 120.2 . .
C3 C4 H4 120.2 7_565 .
C2 C5 H5A 109.5 . .
C2 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C2 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
C7 C6 C7 122.45(13) . 7_565
C7 C6 N2 118.63(7) . .
C7 C6 N2 118.63(7) 7_565 .
C8 C7 C6 117.75(10) . .
C8 C7 C10 121.29(10) . .
C6 C7 C10 120.96(10) . .
C9 C8 C7 121.01(11) . .
C9 C8 H8 119.5 . .
C7 C8 H8 119.5 . .
C8 C9 C8 119.99(15) . 7_565
C8 C9 H9 120.0 . .
C8 C9 H9 120.0 7_565 .
C7 C10 H10A 109.5 . .
C7 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C7 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C12 C11 C14 124.33(13) . .
C12 C11 B1 105.63(12) . .
C14 C11 B1 130.05(12) . .
C11 C12 C13 113.27(12) . .
C11 C12 H12 123.4 . .
C13 C12 H12 123.4 . .
N2 C13 C12 109.94(12) . .
N2 C13 C17 130.22(13) . .
C12 C13 C17 119.84(12) . .
C11 C14 C16 109.43(7) . .
C11 C14 C16 109.43(7) . 7_565
C16 C14 C16 108.85(12) . 7_565
C11 C14 C15 111.93(11) . .
C16 C14 C15 108.57(8) . .
C16 C14 C15 108.57(8) 7_565 .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C14 C16 H16A 109.5 . .
C14 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C14 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C13 C17 C19 115.78(12) . .
C13 C17 C18 107.29(8) . .
C19 C17 C18 108.86(9) . .
C13 C17 C18 107.29(8) . 7_565
C19 C17 C18 108.86(9) . 7_565
C18 C17 C18 108.55(13) . 7_565
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C17 C19 H19A 109.5 . .
C17 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C17 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 N1 1.3396(19) .
B1 N2 1.5690(19) .
B1 C11 1.596(2) .
N1 C1 1.3810(18) .
N2 C13 1.3109(17) .
N2 C6 1.4458(18) .
C1 C2 1.4132(13) .
C1 C2 1.4132(13) 7_565
C2 C3 1.3938(15) .
C2 C5 1.5013(17) .
C3 C4 1.3856(16) .
C3 H3 0.9500 .
C4 C3 1.3856(16) 7_565
C4 H4 0.9500 .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 C7 1.3942(12) .
C6 C7 1.3942(12) 7_565
C7 C8 1.3923(16) .
C7 C10 1.5016(16) .
C8 C9 1.3830(15) .
C8 H8 0.9500 .
C9 C8 1.3830(15) 7_565
C9 H9 0.9500 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 C12 1.3478(19) .
C11 C14 1.514(2) .
C12 C13 1.465(2) .
C12 H12 0.9500 .
C13 C17 1.5147(19) .
C14 C16 1.5323(13) .
C14 C16 1.5323(13) 7_565
C14 C15 1.5340(19) .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 C19 1.527(2) .
C17 C18 1.5400(14) .
C17 C18 1.5400(14) 7_565
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
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
N2 B1 N1 C1 180.0 . .
C11 B1 N1 C1 0.0 . .
N1 B1 N2 C13 180.0 . .
C11 B1 N2 C13 0.0 . .
N1 B1 N2 C6 0.0 . .
C11 B1 N2 C6 180.0 . .
B1 N1 C1 C2 -91.39(11) . .
B1 N1 C1 C2 91.39(11) . 7_565
N1 C1 C2 C3 176.55(10) . .
C2 C1 C2 C3 -6.22(19) 7_565 .
N1 C1 C2 C5 -1.89(17) . .
C2 C1 C2 C5 175.34(8) 7_565 .
C1 C2 C3 C4 1.93(17) . .
C5 C2 C3 C4 -179.66(11) . .
C2 C3 C4 C3 2.4(2) . 7_565
C13 N2 C6 C7 92.96(10) . .
B1 N2 C6 C7 -87.04(10) . .
C13 N2 C6 C7 -92.96(11) . 7_565
B1 N2 C6 C7 87.04(11) . 7_565
C7 C6 C7 C8 2.5(2) 7_565 .
N2 C6 C7 C8 176.33(10) . .
C7 C6 C7 C10 -178.25(8) 7_565 .
N2 C6 C7 C10 -4.41(17) . .
C6 C7 C8 C9 -0.91(18) . .
C10 C7 C8 C9 179.83(12) . .
C7 C8 C9 C8 -0.6(2) . 7_565
N1 B1 C11 C12 180.0 . .
N2 B1 C11 C12 0.0 . .
N1 B1 C11 C14 0.0 . .
N2 B1 C11 C14 180.0 . .
C14 C11 C12 C13 180.0 . .
B1 C11 C12 C13 0.0 . .
C6 N2 C13 C12 180.0 . .
B1 N2 C13 C12 0.0 . .
C6 N2 C13 C17 0.0 . .
B1 N2 C13 C17 180.0 . .
C11 C12 C13 N2 0.0 . .
C11 C12 C13 C17 180.0 . .
C12 C11 C14 C16 -120.40(8) . .
B1 C11 C14 C16 59.60(8) . .
C12 C11 C14 C16 120.40(8) . 7_565
B1 C11 C14 C16 -59.60(8) . 7_565
C12 C11 C14 C15 0.0 . .
B1 C11 C14 C15 180.0 . .
N2 C13 C17 C19 0.0 . .
C12 C13 C17 C19 180.0 . .
N2 C13 C17 C18 -121.76(9) . .
C12 C13 C17 C18 58.24(9) . .
N2 C13 C17 C18 121.76(9) . 7_565
C12 C13 C17 C18 -58.24(9) . 7_565
