#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:15:01 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178695 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/06/4080663.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_4080663
loop_
_publ_author_name
'Sudhakar, Pagidi'
'Mukherjee, Sanjoy'
'Thilagar, Pakkirisamy'
_publ_section_title
;
 Revisiting Borylanilines: Unique Solid-State Structures and Insight into
 Photophysical Properties
;
_journal_issue                   10
_journal_name_full               Organometallics
_journal_page_first              3129
_journal_paper_doi               10.1021/om301197f
_journal_volume                  32
_journal_year                    2013
_chemical_formula_sum            'C26 H32 B N'
_chemical_formula_weight         369.34
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 107.555(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6020(10)
_cell_length_b                   11.6688(9)
_cell_length_c                   16.4915(15)
_cell_measurement_reflns_used    3285
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.46
_cell_measurement_theta_min      2.54
_cell_volume                     2128.7(3)
_computing_cell_refinement       'bruker saint'
_computing_data_collection       'Bruker Kappa Apex ccd'
_computing_data_reduction        'bruker saint'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  WinGXv1.80.05
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 0.3
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker kappa apex ccd'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_sigmaI/netI    0.0515
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21479
_diffrn_reflns_theta_full        30.52
_diffrn_reflns_theta_max         30.52
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  0.9961
_exptl_absorpt_correction_T_min  0.9935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         3250
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1064
_refine_ls_R_factor_gt           0.0645
_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)+(0.0792P)²+2.0714P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1651
_refine_ls_wR_factor_ref         0.1890
_reflns_number_gt                2106
_reflns_number_total             3250
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om301197f_si_003.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4080663
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
B1 B 0.0000 0.0682(2) 0.2500 0.0223(5) Uani 1 2 d S
N1 N 0.0000 -0.4398(2) 0.2500 0.0454(7) Uani 1 2 d S
C1 C -0.01941(15) 0.13864(14) 0.16545(11) 0.0225(4) Uani 1 1 d .
C2 C 0.04919(15) 0.11708(14) 0.10900(11) 0.0226(4) Uani 1 1 d .
C3 C 0.04151(16) 0.18967(16) 0.04117(12) 0.0269(4) Uani 1 1 d .
H3 H 0.0893 0.1752 0.0061 0.032 Uiso 1 1 calc R
C4 C -0.03576(18) 0.28360(17) 0.02409(12) 0.0323(4) Uani 1 1 d .
C5 C -0.10807(17) 0.30184(16) 0.07643(12) 0.0309(4) Uani 1 1 d .
H5 H -0.1635 0.3618 0.0641 0.037 Uiso 1 1 calc R
C6 C -0.09983(16) 0.23286(15) 0.14682(12) 0.0266(4) Uani 1 1 d .
C7 C 0.13602(16) 0.01762(15) 0.12185(12) 0.0273(4) Uani 1 1 d .
H7A H 0.1798 0.0219 0.0809 0.041 Uiso 1 1 calc R
H7B H 0.0917 -0.0530 0.1146 0.041 Uiso 1 1 calc R
H7C H 0.1918 0.0208 0.1782 0.041 Uiso 1 1 calc R
C8 C -0.0409(2) 0.3596(2) -0.04650(14) 0.0456(6) Uani 1 1 d .
H8A H -0.0967 0.4207 -0.0476 0.068 Uiso 1 1 calc R
H8B H -0.0672 0.3174 -0.0989 0.068 Uiso 1 1 calc R
H8C H 0.0380 0.3909 -0.0398 0.068 Uiso 1 1 calc R
C9 C -0.18158(19) 0.26106(17) 0.20011(15) 0.0379(5) Uani 1 1 d .
H9A H -0.1381 0.3067 0.2480 0.057 Uiso 1 1 calc R
H9B H -0.2080 0.1914 0.2199 0.057 Uiso 1 1 calc R
H9C H -0.2506 0.3030 0.1663 0.057 Uiso 1 1 calc R
C10 C 0.0000 -0.06703(19) 0.2500 0.0216(5) Uani 1 2 d S
C11 C -0.09645(15) -0.12972(14) 0.19489(11) 0.0221(4) Uani 1 1 d .
C12 C -0.09541(15) -0.24908(14) 0.19634(11) 0.0230(4) Uani 1 1 d .
H12 H -0.1604 -0.2887 0.1604 0.028 Uiso 1 1 calc R
C13 C 0.0000 -0.3108(2) 0.2500 0.0244(5) Uani 1 2 d S
C14 C -0.20474(16) -0.07079(16) 0.13506(13) 0.0289(4) Uani 1 1 d .
H14A H -0.2641 -0.1271 0.1077 0.043 Uiso 1 1 calc R
H14B H -0.1801 -0.0293 0.0928 0.043 Uiso 1 1 calc R
H14C H -0.2388 -0.0186 0.1665 0.043 Uiso 1 1 calc R
H1 H -0.071(4) -0.480(4) 0.281(3) 0.135(15) Uiso 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'
N N 0.0061 0.0033 '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'
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
C1 B1 C1 117.1(2) 2 .
C1 B1 C10 121.46(10) 2 .
C1 B1 C10 121.46(10) . .
C6 C1 C2 117.35(16) . .
C6 C1 B1 120.45(14) . .
C2 C1 B1 122.00(14) . .
C3 C2 C1 120.65(15) . .
C3 C2 C7 117.49(15) . .
C1 C2 C7 121.82(15) . .
C2 C3 C4 121.78(16) . .
C5 C4 C3 117.92(17) . .
C5 C4 C8 121.25(17) . .
C3 C4 C8 120.83(18) . .
C4 C5 C6 121.80(16) . .
C5 C6 C1 120.37(16) . .
C5 C6 C9 117.51(16) . .
C1 C6 C9 122.11(16) . .
C11 C10 C11 117.7(2) . 2
C11 C10 B1 121.15(10) . .
C11 C10 B1 121.15(10) 2 .
C12 C11 C10 120.34(17) . .
C12 C11 C14 117.91(16) . .
C10 C11 C14 121.73(15) . .
C13 C12 C11 121.97(17) . .
C12 C13 C12 117.7(2) 2 .
C12 C13 N1 121.17(11) 2 .
C12 C13 N1 121.17(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 C1 1.575(2) 2
B1 C1 1.575(2) .
B1 C10 1.578(3) .
N1 C13 1.505(3) .
C1 C6 1.415(2) .
C1 C2 1.418(2) .
C2 C3 1.384(2) .
C2 C7 1.509(2) .
C3 C4 1.390(2) .
C4 C5 1.390(3) .
C4 C8 1.450(3) .
C5 C6 1.392(3) .
C6 C9 1.511(3) .
C10 C11 1.414(2) .
C10 C11 1.414(2) 2
C11 C12 1.393(2) .
C11 C14 1.509(2) .
C12 C13 1.392(2) .
C13 C12 1.392(2) 2
