#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/80/7118019.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_7118019
loop_
_publ_author_name
'Aslam C. Shaikh'
'Dnyanesh S. Ranade'
'Shridhar Thorat'
'Arunava Maity'
'Prasad P. Kulkarni'
'Rajesh G. Gonnade'
'Parthapratim Munshi'
'Nitin T. Patil'
_publ_section_title
;
 Highly emissive organic solids with remarkably broad color tunability
 based on N,C-chelate, four-coordinate organoborons
;
_journal_name_full               Chem.Commun.
_journal_page_first              16115
_journal_paper_doi               10.1039/C5cc06351e
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C21 H25 B N2'
_chemical_formula_sum            'C21 H25 B N2'
_chemical_formula_weight         316.24
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-06-25 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;
_cell_angle_alpha                106.476(2)
_cell_angle_beta                 90.570(2)
_cell_angle_gamma                116.512(2)
_cell_formula_units_Z            2
_cell_length_a                   7.9636(2)
_cell_length_b                   8.8054(2)
_cell_length_c                   14.8492(5)
_cell_measurement_reflns_used    6662
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      33.66
_cell_measurement_theta_min      2.65
_cell_volume                     882.12(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II 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  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12311
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.45
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.9857
_exptl_absorpt_correction_T_min  0.9764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)
_exptl_crystal_colour            ORANGE
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             340
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3115
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0417
_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)+(0.0448P)²+0.3717P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1044
_reflns_number_gt                2747
_reflns_number_total             3115
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc06351e2.cif
_cod_data_source_block           bn_602_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed to 'constr'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 4093 2015-10-18 17:28:56Z antanas 
;
_cod_original_cell_volume        882.12(4)
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               7118019
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.11592(16) 0.16192(14) 0.29181(8) 0.0234(3) Uani 1 1 d . . .
N2 N 0.52163(19) 0.24100(17) -0.05091(9) 0.0342(3) Uani 1 1 d . . .
B1 B 0.3000(2) 0.3335(2) 0.27638(11) 0.0243(3) Uani 1 1 d . . .
C1 C 0.05535(19) 0.01526(18) 0.21398(10) 0.0249(3) Uani 1 1 d . . .
C2 C -0.0963(2) -0.15065(19) 0.21265(11) 0.0308(3) Uani 1 1 d . . .
H2 H -0.1345 -0.2541 0.1584 0.037 Uiso 1 1 calc R . .
C3 C -0.1867(2) -0.16133(19) 0.28887(11) 0.0327(4) Uani 1 1 d . . .
H3 H -0.2887 -0.2727 0.2879 0.039 Uiso 1 1 calc R . .
C4 C -0.1311(2) -0.00851(19) 0.37017(11) 0.0288(3) Uani 1 1 d . . .
C5 C 0.0256(2) 0.15433(19) 0.37060(10) 0.0255(3) Uani 1 1 d . . .
C6 C 0.0863(2) 0.3065(2) 0.45196(10) 0.0309(3) Uani 1 1 d . . .
H6 H 0.1922 0.4161 0.4537 0.037 Uiso 1 1 calc R . .
C7 C -0.0075(2) 0.2965(2) 0.52884(11) 0.0344(4) Uani 1 1 d . . .
H7 H 0.0344 0.4000 0.5834 0.041 Uiso 1 1 calc R . .
C8 C -0.1635(2) 0.1371(2) 0.52826(12) 0.0369(4) Uani 1 1 d . . .
H8 H -0.2274 0.1328 0.5819 0.044 Uiso 1 1 calc R . .
C9 C -0.2238(2) -0.0124(2) 0.45062(12) 0.0351(4) Uani 1 1 d . . .
H9 H -0.3297 -0.1207 0.4506 0.042 Uiso 1 1 calc R . .
C10 C 0.16353(19) 0.05306(18) 0.13886(10) 0.0244(3) Uani 1 1 d . . .
C11 C 0.30748(19) 0.23179(18) 0.16875(10) 0.0235(3) Uani 1 1 d . . .
C12 C 0.4871(2) 0.39288(18) 0.35041(10) 0.0278(3) Uani 1 1 d . . .
H12A H 0.6001 0.4741 0.3292 0.033 Uiso 1 1 calc R . .
H12B H 0.4773 0.4627 0.4135 0.033 Uiso 1 1 calc R . .
C13 C 0.5216(2) 0.2428(2) 0.36267(12) 0.0392(4) Uani 1 1 d . . .
H13A H 0.4144 0.1645 0.3872 0.059 Uiso 1 1 calc R . .
H13B H 0.6388 0.2943 0.4076 0.059 Uiso 1 1 calc R . .
H13C H 0.5337 0.1729 0.3011 0.059 Uiso 1 1 calc R . .
C14 C 0.2512(2) 0.49717(18) 0.28257(10) 0.0269(3) Uani 1 1 d . . .
H14A H 0.2581 0.5600 0.3504 0.032 Uiso 1 1 calc R . .
H14B H 0.3512 0.5838 0.2574 0.032 Uiso 1 1 calc R . .
C15 C 0.0578(2) 0.4437(2) 0.22926(11) 0.0339(4) Uani 1 1 d . . .
H15A H 0.0457 0.3755 0.1626 0.051 Uiso 1 1 calc R . .
H15B H 0.0472 0.5518 0.2327 0.051 Uiso 1 1 calc R . .
H15C H -0.0434 0.3696 0.2584 0.051 Uiso 1 1 calc R . .
C16 C 0.4276(2) 0.29269(19) 0.10573(10) 0.0262(3) Uani 1 1 d . . .
H16 H 0.5268 0.4129 0.1256 0.031 Uiso 1 1 calc R . .
C17 C 0.4050(2) 0.17903(19) 0.01244(10) 0.0276(3) Uani 1 1 d . . .
C18 C 0.2574(2) 0.0001(2) -0.01497(10) 0.0296(3) Uani 1 1 d . . .
H18 H 0.2405 -0.0783 -0.0773 0.036 Uiso 1 1 calc R . .
C19 C 0.1384(2) -0.06200(19) 0.04697(10) 0.0283(3) Uani 1 1 d . . .
H19 H 0.0395 -0.1823 0.0276 0.034 Uiso 1 1 calc R . .
C20 C 0.6946(2) 0.4099(2) -0.01640(12) 0.0390(4) Uani 1 1 d . . .
H20A H 0.6625 0.5076 0.0087 0.058 Uiso 1 1 calc R . .
H20B H 0.7666 0.4296 -0.0688 0.058 Uiso 1 1 calc R . .
H20C H 0.7717 0.4067 0.0342 0.058 Uiso 1 1 calc R . .
C21 C 0.5084(2) 0.1156(2) -0.14249(10) 0.0366(4) Uani 1 1 d . . .
H21A H 0.5335 0.0219 -0.1323 0.055 Uiso 1 1 calc R . .
H21B H 0.6023 0.1797 -0.1782 0.055 Uiso 1 1 calc R . .
H21C H 0.3806 0.0608 -0.1786 0.055 Uiso 1 1 calc R . .
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 N1 C5 120.41(12) . .
C1 N1 B1 111.00(11) . .
C5 N1 B1 128.60(11) . .
C17 N2 C20 119.47(12) . .
C17 N2 C21 119.53(13) . .
C20 N2 C21 117.75(13) . .
C11 B1 C12 112.77(11) . .
C11 B1 C14 111.99(11) . .
C12 B1 C14 113.36(11) . .
C11 B1 N1 96.40(10) . .
C12 B1 N1 110.20(11) . .
C14 B1 N1 110.91(11) . .
N1 C1 C2 120.91(13) . .
N1 C1 C10 111.66(12) . .
C2 C1 C10 127.42(13) . .
C3 C2 C1 119.69(14) . .
C3 C2 H2 120.2 . .
C1 C2 H2 120.2 . .
C2 C3 C4 120.73(13) . .
C2 C3 H3 119.6 . .
C4 C3 H3 119.6 . .
C9 C4 C3 122.73(14) . .
C9 C4 C5 119.05(14) . .
C3 C4 C5 118.22(13) . .
N1 C5 C6 121.02(13) . .
N1 C5 C4 119.96(13) . .
C6 C5 C4 119.02(13) . .
C7 C6 C5 119.98(14) . .
C7 C6 H6 120.0 . .
C5 C6 H6 120.0 . .
C6 C7 C8 121.21(15) . .
C6 C7 H7 119.4 . .
C8 C7 H7 119.4 . .
C9 C8 C7 119.84(14) . .
C9 C8 H8 120.1 . .
C7 C8 H8 120.1 . .
C8 C9 C4 120.89(15) . .
C8 C9 H9 119.6 . .
C4 C9 H9 119.6 . .
C19 C10 C11 121.21(13) . .
C19 C10 C1 128.35(13) . .
C11 C10 C1 110.44(12) . .
C16 C11 C10 118.72(13) . .
C16 C11 B1 130.84(12) . .
C10 C11 B1 110.44(12) . .
C13 C12 B1 116.72(12) . .
C13 C12 H12A 108.1 . .
B1 C12 H12A 108.1 . .
C13 C12 H12B 108.1 . .
B1 C12 H12B 108.1 . .
H12A C12 H12B 107.3 . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C15 C14 B1 115.93(12) . .
C15 C14 H14A 108.3 . .
B1 C14 H14A 108.3 . .
C15 C14 H14B 108.3 . .
B1 C14 H14B 108.3 . .
H14A C14 H14B 107.4 . .
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 . .
C11 C16 C17 121.15(13) . .
C11 C16 H16 119.4 . .
C17 C16 H16 119.4 . .
N2 C17 C16 121.09(13) . .
N2 C17 C18 120.61(13) . .
C16 C17 C18 118.29(13) . .
C19 C18 C17 121.07(13) . .
C19 C18 H18 119.5 . .
C17 C18 H18 119.5 . .
C18 C19 C10 119.55(13) . .
C18 C19 H19 120.2 . .
C10 C19 H19 120.2 . .
N2 C20 H20A 109.5 . .
N2 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
N2 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
N2 C21 H21A 109.5 . .
N2 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
N2 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.3499(17) .
N1 C5 1.3817(18) .
N1 B1 1.6463(19) .
N2 C17 1.3787(19) .
N2 C20 1.448(2) .
N2 C21 1.4565(19) .
B1 C11 1.612(2) .
B1 C12 1.627(2) .
B1 C14 1.631(2) .
C1 C2 1.415(2) .
C1 C10 1.439(2) .
C2 C3 1.350(2) .
C2 H2 0.9500 .
C3 C4 1.414(2) .
C3 H3 0.9500 .
C4 C9 1.411(2) .
C4 C5 1.418(2) .
C5 C6 1.407(2) .
C6 C7 1.373(2) .
C6 H6 0.9500 .
C7 C8 1.397(2) .
C7 H7 0.9500 .
C8 C9 1.362(2) .
C8 H8 0.9500 .
C9 H9 0.9500 .
C10 C19 1.3991(19) .
C10 C11 1.4039(19) .
C11 C16 1.387(2) .
C12 C13 1.522(2) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 C15 1.529(2) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 C17 1.4146(19) .
C16 H16 0.9500 .
C17 C18 1.415(2) .
C18 C19 1.373(2) .
C18 H18 0.9500 .
C19 H19 0.9500 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 N1 B1 C11 1.78(13) . . . .
C5 N1 B1 C11 -178.51(12) . . . .
C1 N1 B1 C12 -115.36(12) . . . .
C5 N1 B1 C12 64.34(16) . . . .
C1 N1 B1 C14 118.28(12) . . . .
C5 N1 B1 C14 -62.01(17) . . . .
C5 N1 C1 C2 -2.56(19) . . . .
B1 N1 C1 C2 177.17(12) . . . .
C5 N1 C1 C10 177.82(11) . . . .
B1 N1 C1 C10 -2.45(15) . . . .
N1 C1 C2 C3 2.5(2) . . . .
C10 C1 C2 C3 -177.97(13) . . . .
C1 C2 C3 C4 -0.1(2) . . . .
C2 C3 C4 C9 178.63(14) . . . .
C2 C3 C4 C5 -2.0(2) . . . .
C1 N1 C5 C6 -179.52(12) . . . .
B1 N1 C5 C6 0.8(2) . . . .
C1 N1 C5 C4 0.34(19) . . . .
B1 N1 C5 C4 -179.34(12) . . . .
C9 C4 C5 N1 -178.69(12) . . . .
C3 C4 C5 N1 1.91(19) . . . .
C9 C4 C5 C6 1.2(2) . . . .
C3 C4 C5 C6 -178.22(13) . . . .
N1 C5 C6 C7 178.96(13) . . . .
C4 C5 C6 C7 -0.9(2) . . . .
C5 C6 C7 C8 0.1(2) . . . .
C6 C7 C8 C9 0.5(2) . . . .
C7 C8 C9 C4 -0.2(2) . . . .
C3 C4 C9 C8 178.75(14) . . . .
C5 C4 C9 C8 -0.6(2) . . . .
N1 C1 C10 C19 -177.28(13) . . . .
C2 C1 C10 C19 3.1(2) . . . .
N1 C1 C10 C11 2.07(16) . . . .
C2 C1 C10 C11 -177.52(13) . . . .
C19 C10 C11 C16 -0.97(19) . . . .
C1 C10 C11 C16 179.62(12) . . . .
C19 C10 C11 B1 178.65(12) . . . .
C1 C10 C11 B1 -0.76(15) . . . .
C12 B1 C11 C16 -65.90(18) . . . .
C14 B1 C11 C16 63.39(19) . . . .
N1 B1 C11 C16 179.02(13) . . . .
C12 B1 C11 C10 114.54(13) . . . .
C14 B1 C11 C10 -116.17(13) . . . .
N1 B1 C11 C10 -0.54(13) . . . .
C11 B1 C12 C13 -62.49(17) . . . .
C14 B1 C12 C13 168.93(13) . . . .
N1 B1 C12 C13 43.96(16) . . . .
C11 B1 C14 C15 62.26(16) . . . .
C12 B1 C14 C15 -168.76(12) . . . .
N1 B1 C14 C15 -44.17(16) . . . .
C10 C11 C16 C17 1.0(2) . . . .
B1 C11 C16 C17 -178.54(13) . . . .
C20 N2 C17 C16 14.0(2) . . . .
C21 N2 C17 C16 173.16(13) . . . .
C20 N2 C17 C18 -166.99(13) . . . .
C21 N2 C17 C18 -7.8(2) . . . .
C11 C16 C17 N2 178.40(12) . . . .
C11 C16 C17 C18 -0.6(2) . . . .
N2 C17 C18 C19 -178.78(13) . . . .
C16 C17 C18 C19 0.3(2) . . . .
C17 C18 C19 C10 -0.3(2) . . . .
C11 C10 C19 C18 0.6(2) . . . .
C1 C10 C19 C18 179.90(13) . . . .
