#------------------------------------------------------------------------------
#$Date: 2016-03-25 23:13:35 +0200 (Fri, 25 Mar 2016) $
#$Revision: 180030 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/24/7032462.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_7032462
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         'C10 H20 B F2 N3 O2'
_chemical_formula_sum            'C10 H20 B F2 N3 O2'
_chemical_formula_weight         263.10
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 96.136(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.6470(8)
_cell_length_b                   19.055(3)
_cell_length_c                   11.3230(18)
_cell_measurement_reflns_used    3191
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.90
_cell_measurement_theta_min      2.10
_cell_volume                     996.9(3)
_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 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10375
_diffrn_reflns_theta_full        27.89
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         2.10
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  0.9928
_exptl_absorpt_correction_T_min  0.9661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0368
_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)+(0.0493P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0910
_reflns_number_gt                1737
_reflns_number_total             2350
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7031751
_cod_data_source_file            c4dt01735h2.cif
_cod_data_source_block           shelxl
_cod_database_code               7032462
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
F1 F 0.44476(17) 0.41803(4) 0.37036(7) 0.0207(2) Uani 1 1 d .
F2 F 0.00538(17) 0.36858(4) 0.38296(6) 0.0200(2) Uani 1 1 d .
O1 O 0.0437(2) 0.48961(5) 0.35127(8) 0.0192(2) Uani 1 1 d .
O2 O 0.8089(2) 0.23225(5) 0.22630(9) 0.0220(3) Uani 1 1 d .
N1 N -0.2472(3) 0.49714(6) 0.17234(10) 0.0171(3) Uani 1 1 d .
N2 N 0.1086(2) 0.40548(6) 0.19043(9) 0.0139(3) Uani 1 1 d .
N3 N 0.4642(2) 0.31692(6) 0.20323(10) 0.0153(3) Uani 1 1 d .
C1 C -0.2937(3) 0.58197(8) 0.32752(13) 0.0234(3) Uani 1 1 d .
H1A H -0.3930 0.5686 0.3963 0.028 Uiso 1 1 calc R
H1B H -0.4333 0.6028 0.2664 0.028 Uiso 1 1 calc R
H1C H -0.1418 0.6162 0.3521 0.028 Uiso 1 1 calc R
C2 C -0.1623(3) 0.51888(7) 0.27879(12) 0.0177(3) Uani 1 1 d .
C3 C -0.1082(3) 0.44168(7) 0.12517(11) 0.0150(3) Uani 1 1 d .
C4 C -0.1945(3) 0.42320(7) 0.00742(11) 0.0167(3) Uani 1 1 d .
H4 H -0.3428 0.4490 -0.0377 0.020 Uiso 1 1 calc R
C5 C -0.0650(3) 0.36789(7) -0.04274(11) 0.0165(3) Uani 1 1 d .
H5 H -0.1273 0.3546 -0.1222 0.020 Uiso 1 1 calc R
C6 C 0.1586(3) 0.33067(7) 0.02201(11) 0.0151(3) Uani 1 1 d .
C7 C 0.2430(3) 0.35174(7) 0.13863(11) 0.0142(3) Uani 1 1 d .
C8 C 0.6109(3) 0.25936(7) 0.16182(12) 0.0169(3) Uani 1 1 d .
C9 C 0.5120(3) 0.23671(7) 0.04238(12) 0.0184(3) Uani 1 1 d .
H9 H 0.5987 0.1969 0.0100 0.022 Uiso 1 1 calc R
C10 C 0.2989(3) 0.27113(7) -0.02357(12) 0.0177(3) Uani 1 1 d .
H10 H 0.2402 0.2556 -0.1022 0.021 Uiso 1 1 calc R
B1 B 0.1538(4) 0.42042(8) 0.32946(13) 0.0159(3) Uani 1 1 d .
H2 H 0.537(3) 0.3327(9) 0.2747(15) 0.030(5) 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'
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 121.81(11)
C2 N1 C3 119.85(12)
C7 N2 C3 119.34(11)
C7 N2 B1 122.78(11)
C3 N2 B1 117.07(11)
C7 N3 C8 124.51(12)
C7 N3 H2 120.7(10)
C8 N3 H2 114.5(11)
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 124.99(13)
N1 C2 C1 120.62(12)
O1 C2 C1 114.39(12)
N2 C3 N1 121.73(12)
N2 C3 C4 120.51(12)
N1 C3 C4 117.76(12)
C5 C4 C3 119.81(12)
C5 C4 H4 120.1
C3 C4 H4 120.1
C4 C5 C6 120.56(12)
C4 C5 H5 119.7
C6 C5 H5 119.7
C7 C6 C5 117.90(13)
C7 C6 C10 118.43(12)
C5 C6 C10 123.65(12)
N2 C7 N3 119.12(12)
N2 C7 C6 121.83(12)
N3 C7 C6 119.05(13)
O2 C8 N3 119.51(12)
O2 C8 C9 125.06(13)
N3 C8 C9 115.43(12)
C10 C9 C8 121.00(13)
C10 C9 H9 119.5
C8 C9 H9 119.5
C9 C10 C6 121.51(12)
C9 C10 H10 119.2
C6 C10 H10 119.2
F2 B1 F1 110.24(11)
F2 B1 O1 112.03(13)
F1 B1 O1 108.92(12)
F2 B1 N2 106.65(11)
F1 B1 N2 110.27(12)
O1 B1 N2 108.70(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 B1 1.3823(18)
F2 B1 1.3812(18)
O1 C2 1.3167(16)
O1 B1 1.4448(18)
O2 C8 1.2256(16)
N1 C2 1.2956(17)
N1 C3 1.3760(18)
N2 C7 1.3643(17)
N2 C3 1.3703(17)
N2 B1 1.5915(18)
N3 C7 1.3678(17)
N3 C8 1.3987(18)
N3 H2 0.895(17)
C1 C2 1.481(2)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C3 C4 1.3958(17)
C4 C5 1.3669(19)
C4 H4 0.9500
C5 C6 1.3989(19)
C5 H5 0.9500
C6 C7 1.3958(18)
C6 C10 1.4320(19)
C8 C9 1.4470(19)
C9 C10 1.3453(19)
C9 H9 0.9500
C10 H10 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H2 F2 0.895(17) 2.477(16) 3.2159(14) 140.1(14) 1_655
N3 H2 F1 0.895(17) 2.025(17) 2.7089(14) 132.2(14) .
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 -3.6(2)
C3 N1 C2 C1 175.11(13)
B1 O1 C2 N1 -14.2(2)
B1 O1 C2 C1 166.95(13)
C7 N2 C3 N1 -178.77(12)
B1 N2 C3 N1 11.20(19)
C7 N2 C3 C4 1.0(2)
B1 N2 C3 C4 -169.00(12)
C2 N1 C3 N2 4.1(2)
C2 N1 C3 C4 -175.75(13)
N2 C3 C4 C5 1.0(2)
N1 C3 C4 C5 -179.18(13)
C3 C4 C5 C6 -1.6(2)
C4 C5 C6 C7 0.2(2)
C4 C5 C6 C10 178.30(14)
C3 N2 C7 N3 178.38(12)
B1 N2 C7 N3 -12.2(2)
C3 N2 C7 C6 -2.5(2)
B1 N2 C7 C6 166.93(12)
C8 N3 C7 N2 177.37(12)
C8 N3 C7 C6 -1.8(2)
C5 C6 C7 N2 1.9(2)
C10 C6 C7 N2 -176.31(12)
C5 C6 C7 N3 -178.98(12)
C10 C6 C7 N3 2.8(2)
C7 N3 C8 O2 179.15(13)
C7 N3 C8 C9 -0.6(2)
O2 C8 C9 C10 -177.76(14)
N3 C8 C9 C10 2.0(2)
C8 C9 C10 C6 -1.0(2)
C7 C6 C10 C9 -1.5(2)
C5 C6 C10 C9 -179.58(14)
C2 O1 B1 F2 -91.07(15)
C2 O1 B1 F1 146.71(12)
C2 O1 B1 N2 26.53(18)
C7 N2 B1 F2 -73.38(16)
C3 N2 B1 F2 96.28(13)
C7 N2 B1 F1 46.32(17)
C3 N2 B1 F1 -144.03(12)
C7 N2 B1 O1 165.65(12)
C3 N2 B1 O1 -24.69(17)
