#------------------------------------------------------------------------------
#$Date: 2016-03-25 23:13:35 +0200 (Fri, 25 Mar 2016) $
#$Revision: 180030 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/24/7032461.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_7032461
loop_
_publ_author_name
'Du, Mei-Ling'
'Hu, Chun-Yan'
'Wang, Liu-Fang'
'Li, Cong'
'Han, Yang-Yang'
'Gan, Xin'
'Chen, Yong'
'Mu, Wei-Hua'
'Huang, Michael L.'
'Fu, Wen-Fu'
_publ_section_title
;
 New members of fluorescent 1,8-naphthyridine-based BF2 compounds:
 selective binding of BF2 with terminal bidentate NNO and NCO groups
 and tunable spectroscopy properties.
;
_journal_issue                   37
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              13924
_journal_page_last               13931
_journal_paper_doi               10.1039/c4dt01735h
_journal_volume                  43
_journal_year                    2014
_chemical_formula_moiety         'C12 H12 B F2 N3 O'
_chemical_formula_sum            'C12 H12 B F2 N3 O'
_chemical_formula_weight         263.06
_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
_cell_angle_alpha                93.34(2)
_cell_angle_beta                 107.60(2)
_cell_angle_gamma                94.49(3)
_cell_formula_units_Z            2
_cell_length_a                   7.2978(8)
_cell_length_b                   8.1140(10)
_cell_length_c                   10.4990(13)
_cell_measurement_reflns_used    2719
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      31.40
_cell_measurement_theta_min      2.00
_cell_volume                     588.57(14)
_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    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.222
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8233
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         2.04
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.9746
_exptl_absorpt_correction_T_min  0.9633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3324
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0476
_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)+(0.0834P)²+0.1530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1337
_refine_ls_wR_factor_ref         0.1369
_reflns_number_gt                3079
_reflns_number_total             3324
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7031750
_cod_data_source_file            c4dt01735h2.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        588.57(12)
_cod_database_code               7032461
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
F1 F 0.32138(9) 0.60150(7) 0.67046(6) 0.02060(16) Uani 1 1 d .
F2 F 0.26703(9) 0.61477(7) 0.87366(6) 0.02048(16) Uani 1 1 d .
O1 O 0.57827(11) 0.66088(9) 0.86353(8) 0.02028(18) Uani 1 1 d .
N1 N 0.69147(12) 0.94023(11) 0.90323(9) 0.01891(19) Uani 1 1 d .
N2 N 0.35315(12) 0.87442(10) 0.78949(8) 0.01514(18) Uani 1 1 d .
N3 N 0.02685(12) 0.80698(11) 0.67950(9) 0.01697(19) Uani 1 1 d .
C1 C 0.91064(15) 0.73022(14) 0.97229(11) 0.0216(2) Uani 1 1 d .
H1A H 0.9031 0.6455 1.0339 0.026 Uiso 1 1 calc R
H1B H 0.9982 0.8262 1.0220 0.026 Uiso 1 1 calc R
H1C H 0.9595 0.6842 0.9019 0.026 Uiso 1 1 calc R
C2 C 0.71473(14) 0.78298(13) 0.91012(10) 0.0174(2) Uani 1 1 d .
C3 C 0.51031(14) 0.98539(13) 0.84181(10) 0.0166(2) Uani 1 1 d .
C4 C 0.49378(15) 1.15830(13) 0.83515(10) 0.0195(2) Uani 1 1 d .
H4 H 0.6050 1.2354 0.8720 0.023 Uiso 1 1 calc R
C5 C 0.31981(15) 1.21384(12) 0.77643(10) 0.0191(2) Uani 1 1 d .
H5 H 0.3097 1.3296 0.7729 0.023 Uiso 1 1 calc R
C6 C 0.15260(14) 1.09919(12) 0.72022(10) 0.0163(2) Uani 1 1 d .
C7 C 0.17317(14) 0.92796(12) 0.72846(9) 0.01522(19) Uani 1 1 d .
C8 C -0.14668(15) 0.85292(13) 0.61878(10) 0.0180(2) Uani 1 1 d .
C9 C -0.18151(15) 1.02046(13) 0.60524(10) 0.0193(2) Uani 1 1 d .
H9 H -0.3083 1.0469 0.5605 0.023 Uiso 1 1 calc R
C10 C -0.03460(15) 1.14651(13) 0.65585(10) 0.0182(2) Uani 1 1 d .
C11 C -0.30792(15) 0.71631(13) 0.56354(11) 0.0228(2) Uani 1 1 d .
H11A H -0.2828 0.6489 0.4912 0.027 Uiso 1 1 calc R
H11B H -0.4303 0.7646 0.5283 0.027 Uiso 1 1 calc R
H11C H -0.3158 0.6463 0.6350 0.027 Uiso 1 1 calc R
C12 C -0.07162(16) 1.32478(13) 0.64202(11) 0.0236(2) Uani 1 1 d .
H12A H -0.0245 1.3869 0.7305 0.028 Uiso 1 1 calc R
H12B H -0.2107 1.3319 0.6036 0.028 Uiso 1 1 calc R
H12C H -0.0039 1.3720 0.5829 0.028 Uiso 1 1 calc R
B1 B 0.37280(16) 0.68174(14) 0.79738(11) 0.0166(2) Uani 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
C2 O1 B1 124.60(8)
C2 N1 C3 118.82(9)
C3 N2 C7 120.45(9)
C3 N2 B1 120.07(9)
C7 N2 B1 119.48(8)
C8 N3 C7 117.30(9)
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N1 C2 O1 125.46(9)
N1 C2 C1 119.99(10)
O1 C2 C1 114.54(9)
N2 C3 N1 123.14(9)
N2 C3 C4 120.39(9)
N1 C3 C4 116.47(9)
C5 C4 C3 120.35(10)
C5 C4 H4 119.8
C3 C4 H4 119.8
C4 C5 C6 120.22(9)
C4 C5 H5 119.9
C6 C5 H5 119.9
C7 C6 C10 117.86(9)
C7 C6 C5 118.24(9)
C10 C6 C5 123.90(9)
N3 C7 N2 115.48(9)
N3 C7 C6 124.16(9)
N2 C7 C6 120.36(9)
N3 C8 C9 122.71(10)
N3 C8 C11 116.62(9)
C9 C8 C11 120.67(9)
C10 C9 C8 121.05(10)
C10 C9 H9 119.5
C8 C9 H9 119.5
C9 C10 C6 116.90(9)
C9 C10 C12 121.10(10)
C6 C10 C12 121.99(10)
C8 C11 H11A 109.5
C8 C11 H11B 109.5
H11A C11 H11B 109.5
C8 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C10 C12 H12A 109.5
C10 C12 H12B 109.5
H12A C12 H12B 109.5
C10 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
F2 B1 F1 112.04(9)
F2 B1 O1 107.97(8)
F1 B1 O1 107.44(8)
F2 B1 N2 110.87(8)
F1 B1 N2 110.47(8)
O1 B1 N2 107.87(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 B1 1.3780(12)
F2 B1 1.3753(13)
O1 C2 1.3066(13)
O1 B1 1.4775(13)
N1 C2 1.3035(14)
N1 C3 1.3732(13)
N2 C3 1.3519(13)
N2 C7 1.3918(13)
N2 B1 1.5858(14)
N3 C8 1.3276(13)
N3 C7 1.3466(13)
C1 C2 1.4891(14)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C3 C4 1.4215(14)
C4 C5 1.3578(15)
C4 H4 0.9500
C5 C6 1.4232(14)
C5 H5 0.9500
C6 C7 1.4139(14)
C6 C10 1.4228(14)
C8 C9 1.4099(14)
C8 C11 1.5026(15)
C9 C10 1.3778(15)
C9 H9 0.9500
C10 C12 1.4995(14)
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 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
C3 N1 C2 O1 -0.39(16)
C3 N1 C2 C1 178.06(8)
B1 O1 C2 N1 -1.36(16)
B1 O1 C2 C1 -179.89(8)
C7 N2 C3 N1 179.98(8)
B1 N2 C3 N1 0.00(14)
C7 N2 C3 C4 0.00(15)
B1 N2 C3 C4 -179.98(8)
C2 N1 C3 N2 1.02(15)
C2 N1 C3 C4 -179.00(9)
N2 C3 C4 C5 0.15(16)
N1 C3 C4 C5 -179.83(9)
C3 C4 C5 C6 -0.41(16)
C4 C5 C6 C7 0.51(15)
C4 C5 C6 C10 -179.40(9)
C8 N3 C7 N2 -179.05(8)
C8 N3 C7 C6 0.64(15)
C3 N2 C7 N3 179.82(8)
B1 N2 C7 N3 -0.20(13)
C3 N2 C7 C6 0.11(14)
B1 N2 C7 C6 -179.91(8)
C10 C6 C7 N3 -0.13(15)
C5 C6 C7 N3 179.96(9)
C10 C6 C7 N2 179.55(8)
C5 C6 C7 N2 -0.36(14)
C7 N3 C8 C9 -0.43(15)
C7 N3 C8 C11 179.42(8)
N3 C8 C9 C10 -0.30(16)
C11 C8 C9 C10 179.85(9)
C8 C9 C10 C6 0.80(15)
C8 C9 C10 C12 -179.75(9)
C7 C6 C10 C9 -0.59(14)
C5 C6 C10 C9 179.31(9)
C7 C6 C10 C12 179.96(9)
C5 C6 C10 C12 -0.13(16)
C2 O1 B1 F2 -117.79(10)
C2 O1 B1 F1 121.19(10)
C2 O1 B1 N2 2.08(13)
C3 N2 B1 F2 116.63(10)
C7 N2 B1 F2 -63.35(11)
C3 N2 B1 F1 -118.56(10)
C7 N2 B1 F1 61.47(11)
C3 N2 B1 O1 -1.40(12)
C7 N2 B1 O1 178.63(8)
