#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/80/7118018.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_7118018
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         'C25 H20 B N'
_chemical_formula_sum            'C25 H20 B N'
_chemical_formula_weight         345.23
_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
_audit_update_record
;
2015-06-25 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.128(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.9351(7)
_cell_length_b                   9.0239(5)
_cell_length_c                   14.1194(8)
_cell_measurement_reflns_used    9474
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.74
_cell_measurement_theta_min      2.68
_cell_volume                     1774.28(17)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0478
_diffrn_reflns_av_sigmaI/netI    0.0276
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22665
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9927
_exptl_absorpt_correction_T_min  0.9712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             728
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Pet Ether Ethyl Acetate MIxture'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.146
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.212
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3108
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.212
_refine_ls_R_factor_all          0.1655
_refine_ls_R_factor_gt           0.1623
_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)+(0.0891P)²+32.5990P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4284
_refine_ls_wR_factor_ref         0.4295
_reflns_number_gt                2911
_reflns_number_total             3108
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc06351e2.cif
_cod_data_source_block           bn_501_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_sg_symbol_H-M      'P2(1)/n  '
_cod_database_code               7118018
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5035(5) 0.9046(8) 0.1676(5) 0.0202(16) Uani 1 1 d . . .
B1 B 0.5681(7) 0.8026(11) 0.2401(7) 0.025(2) Uani 1 1 d . . .
C1 C 0.4219(6) 0.8352(9) 0.1396(6) 0.0208(18) Uani 1 1 d . . .
C2 C 0.3494(6) 0.9110(9) 0.0872(6) 0.0240(19) Uani 1 1 d . . .
H2 H 0.2905 0.8632 0.0705 0.029 Uiso 1 1 calc R . .
C3 C 0.3651(6) 1.0537(10) 0.0609(6) 0.0237(19) Uani 1 1 d . . .
H3 H 0.3168 1.1050 0.0247 0.028 Uiso 1 1 calc R . .
C4 C 0.4509(6) 1.1264(9) 0.0861(6) 0.0223(19) Uani 1 1 d . . .
C5 C 0.5209(6) 1.0497(10) 0.1414(6) 0.0239(19) Uani 1 1 d . . .
C6 C 0.6083(7) 1.1221(10) 0.1691(7) 0.030(2) Uani 1 1 d . . .
H6 H 0.6566 1.0706 0.2052 0.036 Uiso 1 1 calc R . .
C7 C 0.6218(7) 1.2654(10) 0.1436(7) 0.031(2) Uani 1 1 d . . .
H7 H 0.6795 1.3140 0.1637 0.037 Uiso 1 1 calc R . .
C8 C 0.5528(7) 1.3444(10) 0.0881(6) 0.028(2) Uani 1 1 d . . .
H8 H 0.5646 1.4440 0.0701 0.034 Uiso 1 1 calc R . .
C9 C 0.4695(7) 1.2764(10) 0.0607(6) 0.027(2) Uani 1 1 d . . .
H9 H 0.4227 1.3297 0.0239 0.033 Uiso 1 1 calc R . .
C10 C 0.4199(6) 0.6855(9) 0.1790(6) 0.0223(19) Uani 1 1 d . . .
C11 C 0.4957(6) 0.6634(9) 0.2417(6) 0.0213(18) Uani 1 1 d . . .
C12 C 0.5827(7) 0.8885(10) 0.3397(7) 0.029(2) Uani 1 1 d . . .
H12A H 0.5198 0.9139 0.3641 0.043 Uiso 1 1 calc R . .
H12B H 0.6197 0.9794 0.3302 0.043 Uiso 1 1 calc R . .
H12C H 0.6175 0.8245 0.3853 0.043 Uiso 1 1 calc R . .
C13 C 0.6690(6) 0.7549(11) 0.1896(6) 0.028(2) Uani 1 1 d . . .
H13A H 0.7012 0.6768 0.2271 0.042 Uiso 1 1 calc R . .
H13B H 0.7113 0.8414 0.1865 0.042 Uiso 1 1 calc R . .
H13C H 0.6543 0.7182 0.1254 0.042 Uiso 1 1 calc R . .
C14 C 0.5025(6) 0.5329(10) 0.2978(6) 0.0251(19) Uani 1 1 d . . .
C15 C 0.5810(7) 0.5077(11) 0.3625(7) 0.033(2) Uani 1 1 d . . .
H15 H 0.6324 0.5769 0.3652 0.039 Uiso 1 1 calc R . .
C16 C 0.5852(8) 0.3871(11) 0.4213(7) 0.034(2) Uani 1 1 d . . .
H16 H 0.6386 0.3733 0.4641 0.040 Uiso 1 1 calc R . .
C17 C 0.5095(8) 0.2837(13) 0.4177(7) 0.041(3) Uani 1 1 d . . .
H17 H 0.5116 0.2000 0.4585 0.049 Uiso 1 1 calc R . .
C18 C 0.4323(7) 0.3038(11) 0.3549(7) 0.033(2) Uani 1 1 d . . .
H18 H 0.3812 0.2340 0.3537 0.040 Uiso 1 1 calc R . .
C19 C 0.4276(7) 0.4252(10) 0.2929(6) 0.026(2) Uani 1 1 d . . .
C20 C 0.3495(6) 0.4451(9) 0.2216(6) 0.0227(19) Uani 1 1 d . . .
C21 C 0.3465(6) 0.5693(9) 0.1604(6) 0.0209(18) Uani 1 1 d . . .
C22 C 0.2794(6) 0.5701(9) 0.0849(6) 0.0219(18) Uani 1 1 d . . .
H22 H 0.2800 0.6500 0.0411 0.026 Uiso 1 1 calc R . .
C23 C 0.2129(7) 0.4603(11) 0.0714(7) 0.030(2) Uani 1 1 d . . .
H23 H 0.1684 0.4643 0.0188 0.036 Uiso 1 1 calc R . .
C24 C 0.2104(6) 0.3417(10) 0.1353(6) 0.027(2) Uani 1 1 d . . .
H24 H 0.1622 0.2676 0.1290 0.032 Uiso 1 1 calc R . .
C25 C 0.2791(7) 0.3352(10) 0.2071(7) 0.030(2) Uani 1 1 d . . .
H25 H 0.2791 0.2527 0.2489 0.036 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 121.1(7) . .
C1 N1 B1 111.4(7) . .
C5 N1 B1 127.3(7) . .
C11 B1 C12 114.9(7) . .
C11 B1 N1 96.8(7) . .
C12 B1 N1 109.0(7) . .
C11 B1 C13 110.2(8) . .
C12 B1 C13 114.7(8) . .
N1 B1 C13 109.6(7) . .
N1 C1 C2 120.7(8) . .
N1 C1 C10 110.3(7) . .
C2 C1 C10 128.7(8) . .
C3 C2 C1 119.0(8) . .
C3 C2 H2 120.5 . .
C1 C2 H2 120.5 . .
C2 C3 C4 121.3(8) . .
C2 C3 H3 119.4 . .
C4 C3 H3 119.4 . .
C3 C4 C5 118.6(8) . .
C3 C4 C9 122.9(8) . .
C5 C4 C9 118.5(8) . .
N1 C5 C4 119.2(8) . .
N1 C5 C6 121.1(8) . .
C4 C5 C6 119.7(8) . .
C7 C6 C5 119.3(9) . .
C7 C6 H6 120.4 . .
C5 C6 H6 120.4 . .
C6 C7 C8 122.0(9) . .
C6 C7 H7 119.0 . .
C8 C7 H7 119.0 . .
C9 C8 C7 119.2(9) . .
C9 C8 H8 120.4 . .
C7 C8 H8 120.4 . .
C8 C9 C4 121.3(9) . .
C8 C9 H9 119.4 . .
C4 C9 H9 119.4 . .
C11 C10 C1 110.8(8) . .
C11 C10 C21 121.6(8) . .
C1 C10 C21 127.6(8) . .
C10 C11 C14 121.0(8) . .
C10 C11 B1 110.3(7) . .
C14 C11 B1 128.7(8) . .
B1 C12 H12A 109.5 . .
B1 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
B1 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
B1 C13 H13A 109.5 . .
B1 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
B1 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C15 C14 C11 121.7(8) . .
C15 C14 C19 117.9(8) . .
C11 C14 C19 120.3(8) . .
C16 C15 C14 122.2(9) . .
C16 C15 H15 118.9 . .
C14 C15 H15 118.9 . .
C15 C16 C17 119.4(9) . .
C15 C16 H16 120.3 . .
C17 C16 H16 120.3 . .
C18 C17 C16 120.1(9) . .
C18 C17 H17 120.0 . .
C16 C17 H17 120.0 . .
C17 C18 C19 121.3(10) . .
C17 C18 H18 119.3 . .
C19 C18 H18 119.3 . .
C18 C19 C14 119.1(9) . .
C18 C19 C20 122.7(9) . .
C14 C19 C20 118.2(8) . .
C25 C20 C21 117.7(8) . .
C25 C20 C19 120.7(8) . .
C21 C20 C19 121.4(8) . .
C22 C21 C20 118.4(8) . .
C22 C21 C10 124.9(8) . .
C20 C21 C10 116.6(8) . .
C23 C22 C21 122.4(8) . .
C23 C22 H22 118.8 . .
C21 C22 H22 118.8 . .
C22 C23 C24 119.8(9) . .
C22 C23 H23 120.1 . .
C24 C23 H23 120.1 . .
C25 C24 C23 118.5(8) . .
C25 C24 H24 120.8 . .
C23 C24 H24 120.8 . .
C24 C25 C20 122.9(8) . .
C24 C25 H25 118.6 . .
C20 C25 H25 118.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.344(11) .
N1 C5 1.385(11) .
N1 B1 1.624(11) .
B1 C11 1.611(12) .
B1 C12 1.612(14) .
B1 C13 1.657(14) .
C1 C2 1.407(12) .
C1 C10 1.462(12) .
C2 C3 1.361(12) .
C2 H2 0.9500 .
C3 C4 1.398(13) .
C3 H3 0.9500 .
C4 C5 1.408(12) .
C4 C9 1.427(12) .
C5 C6 1.424(13) .
C6 C7 1.358(13) .
C6 H6 0.9500 .
C7 C8 1.410(13) .
C7 H7 0.9500 .
C8 C9 1.356(13) .
C8 H8 0.9500 .
C9 H9 0.9500 .
C10 C11 1.368(12) .
C10 C21 1.481(12) .
C11 C14 1.420(12) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 C15 1.417(13) .
C14 C19 1.425(13) .
C15 C16 1.368(14) .
C15 H15 0.9500 .
C16 C17 1.407(15) .
C16 H16 0.9500 .
C17 C18 1.380(14) .
C17 H17 0.9500 .
C18 C19 1.403(13) .
C18 H18 0.9500 .
C19 C20 1.466(13) .
C20 C25 1.405(13) .
C20 C21 1.415(12) .
C21 C22 1.392(12) .
C22 C23 1.365(13) .
C22 H22 0.9500 .
C23 C24 1.401(14) .
C23 H23 0.9500 .
C24 C25 1.369(14) .
C24 H24 0.9500 .
C25 H25 0.9500 .
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 -0.6(9) . . . .
C5 N1 B1 C11 173.8(8) . . . .
C1 N1 B1 C12 -120.0(8) . . . .
C5 N1 B1 C12 54.5(11) . . . .
C1 N1 B1 C13 113.7(8) . . . .
C5 N1 B1 C13 -71.9(11) . . . .
C5 N1 C1 C2 -3.7(12) . . . .
B1 N1 C1 C2 171.2(8) . . . .
C5 N1 C1 C10 -178.3(7) . . . .
B1 N1 C1 C10 -3.4(9) . . . .
N1 C1 C2 C3 3.4(13) . . . .
C10 C1 C2 C3 177.0(8) . . . .
C1 C2 C3 C4 -1.0(13) . . . .
C2 C3 C4 C5 -1.2(13) . . . .
C2 C3 C4 C9 -179.3(8) . . . .
C1 N1 C5 C4 1.4(12) . . . .
B1 N1 C5 C4 -172.6(8) . . . .
C1 N1 C5 C6 -178.5(8) . . . .
B1 N1 C5 C6 7.5(13) . . . .
C3 C4 C5 N1 1.0(12) . . . .
C9 C4 C5 N1 179.2(8) . . . .
C3 C4 C5 C6 -179.1(8) . . . .
C9 C4 C5 C6 -0.8(13) . . . .
N1 C5 C6 C7 -178.7(9) . . . .
C4 C5 C6 C7 1.4(14) . . . .
C5 C6 C7 C8 -1.6(15) . . . .
C6 C7 C8 C9 1.3(15) . . . .
C7 C8 C9 C4 -0.7(14) . . . .
C3 C4 C9 C8 178.6(9) . . . .
C5 C4 C9 C8 0.5(13) . . . .
N1 C1 C10 C11 6.9(10) . . . .
C2 C1 C10 C11 -167.2(9) . . . .
N1 C1 C10 C21 -175.5(8) . . . .
C2 C1 C10 C21 10.4(14) . . . .
C1 C10 C11 C14 172.2(7) . . . .
C21 C10 C11 C14 -5.6(12) . . . .
C1 C10 C11 B1 -7.3(10) . . . .
C21 C10 C11 B1 175.0(7) . . . .
C12 B1 C11 C10 119.5(8) . . . .
N1 B1 C11 C10 4.8(9) . . . .
C13 B1 C11 C10 -109.0(8) . . . .
C12 B1 C11 C14 -60.0(12) . . . .
N1 B1 C11 C14 -174.6(8) . . . .
C13 B1 C11 C14 71.5(11) . . . .
C10 C11 C14 C15 179.4(8) . . . .
B1 C11 C14 C15 -1.2(14) . . . .
C10 C11 C14 C19 -3.0(12) . . . .
B1 C11 C14 C19 176.3(8) . . . .
C11 C14 C15 C16 175.6(9) . . . .
C19 C14 C15 C16 -1.9(14) . . . .
C14 C15 C16 C17 0.2(15) . . . .
C15 C16 C17 C18 0.4(16) . . . .
C16 C17 C18 C19 0.8(16) . . . .
C17 C18 C19 C14 -2.6(14) . . . .
C17 C18 C19 C20 176.3(9) . . . .
C15 C14 C19 C18 3.1(12) . . . .
C11 C14 C19 C18 -174.5(8) . . . .
C15 C14 C19 C20 -175.9(8) . . . .
C11 C14 C19 C20 6.5(12) . . . .
C18 C19 C20 C25 -5.4(13) . . . .
C14 C19 C20 C25 173.5(8) . . . .
C18 C19 C20 C21 179.6(8) . . . .
C14 C19 C20 C21 -1.5(12) . . . .
C25 C20 C21 C22 -5.2(11) . . . .
C19 C20 C21 C22 170.0(8) . . . .
C25 C20 C21 C10 178.3(7) . . . .
C19 C20 C21 C10 -6.5(11) . . . .
C11 C10 C21 C22 -166.0(8) . . . .
C1 C10 C21 C22 16.6(13) . . . .
C11 C10 C21 C20 10.2(11) . . . .
C1 C10 C21 C20 -167.2(8) . . . .
C20 C21 C22 C23 4.2(12) . . . .
C10 C21 C22 C23 -179.6(8) . . . .
C21 C22 C23 C24 0.3(13) . . . .
C22 C23 C24 C25 -3.7(13) . . . .
C23 C24 C25 C20 2.6(13) . . . .
C21 C20 C25 C24 1.9(13) . . . .
C19 C20 C25 C24 -173.3(8) . . . .
