#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:50:16 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180278 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/64/7116462.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_7116462
loop_
_publ_author_name
'Liao, Chia-Wei'
'Rao M, Rajeswara'
'Sun, Shih-Sheng'
_publ_section_title
;
 Structural diversity of new solid-state luminophores based on
 quinoxaline-β-ketoiminate boron difluoride complexes with remarkable
 fluorescence switching properties.
;
_journal_issue                   13
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2656
_journal_page_last               2659
_journal_paper_doi               10.1039/c4cc08958h
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C17 H13 B F2 N2 O'
_chemical_formula_sum            'C17 H13 B F2 N2 O'
_chemical_formula_weight         310.1
_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_update_record
;
2013-07-30 deposited with the CCDC.
2014-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                86.948(2)
_cell_angle_beta                 70.9880(10)
_cell_angle_gamma                86.6970(10)
_cell_formula_units_Z            2
_cell_length_a                   7.0915(3)
_cell_length_b                   10.1014(5)
_cell_length_c                   10.3857(5)
_cell_measurement_reflns_used    5101
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.66
_cell_measurement_theta_min      2.84
_cell_volume                     701.75(6)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10745
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    0.11
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.9674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2862
_refine_ls_number_restraints     65
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0465P)²+0.1398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0956
_reflns_number_gt                2204
_reflns_number_total             2862
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc08958h2.cif
_cod_data_source_block           i14573
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7116462
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 0.63148(11) 0.27800(7) 0.86942(8) 0.0218(2) Uani 1 1 d U
F2 F 0.96415(11) 0.26969(8) 0.83669(8) 0.0241(2) Uani 1 1 d U
O2 O 0.81497(14) 0.07853(9) 0.81803(9) 0.0217(2) Uani 1 1 d U
N7 N 0.64851(15) 0.12369(11) 1.32923(11) 0.0177(3) Uani 1 1 d U
N14 N 0.74366(15) 0.17384(11) 1.04786(11) 0.0153(3) Uani 1 1 d U
B B 0.7895(2) 0.20223(15) 0.88865(15) 0.0174(3) Uani 1 1 d U
C3 C 0.78296(18) -0.04145(13) 0.87737(13) 0.0156(3) Uani 1 1 d U
C4 C 0.73312(18) -0.05895(13) 1.01486(13) 0.0167(3) Uani 1 1 d U
H4 H 0.7111 -0.146 1.0544 0.02 Uiso 1 1 calc R
C5 C 0.71301(18) 0.04906(13) 1.10132(13) 0.0149(3) Uani 1 1 d U
C6 C 0.65830(18) 0.02717(13) 1.24837(13) 0.0161(3) Uani 1 1 d U
C8 C 0.68338(19) 0.24991(13) 1.27393(13) 0.0174(3) Uani 1 1 d U
C9 C 0.6681(2) 0.35397(14) 1.36252(14) 0.0213(3) Uani 1 1 d U
H9 H 0.6412 0.3349 1.4572 0.026 Uiso 1 1 calc R
C10 C 0.6919(2) 0.48205(14) 1.31302(15) 0.0242(3) Uani 1 1 d U
H10 H 0.6805 0.5519 1.3732 0.029 Uiso 1 1 calc R
C11 C 0.7331(2) 0.51036(14) 1.17297(15) 0.0234(3) Uani 1 1 d U
H11 H 0.7487 0.5998 1.1394 0.028 Uiso 1 1 calc R
C12 C 0.7515(2) 0.41120(13) 1.08349(14) 0.0209(3) Uani 1 1 d U
H12 H 0.7803 0.4319 0.9889 0.025 Uiso 1 1 calc R
C13 C 0.72731(18) 0.27896(13) 1.13305(13) 0.0168(3) Uani 1 1 d U
C15 C 0.6069(2) -0.10847(13) 1.31135(13) 0.0209(3) Uani 1 1 d U
H15A H 0.4989 -0.141 1.2836 0.031 Uiso 1 1 calc R
H15B H 0.5635 -0.1041 1.4108 0.031 Uiso 1 1 calc R
H15C H 0.7246 -0.169 1.2808 0.031 Uiso 1 1 calc R
C16 C 0.80677(18) -0.14896(13) 0.78121(13) 0.0162(3) Uani 1 1 d U
C17 C 0.8702(2) -0.11854(14) 0.64113(14) 0.0212(3) Uani 1 1 d U
H17 H 0.8972 -0.0296 0.609 0.025 Uiso 1 1 calc R
C18 C 0.8939(2) -0.21761(15) 0.54872(14) 0.0242(3) Uani 1 1 d U
H18 H 0.9383 -0.1964 0.4537 0.029 Uiso 1 1 calc R
C19 C 0.8530(2) -0.34687(14) 0.59483(15) 0.0229(3) Uani 1 1 d U
H19 H 0.869 -0.4143 0.5313 0.027 Uiso 1 1 calc R
C20 C 0.7886(2) -0.37881(14) 0.73341(15) 0.0238(3) Uani 1 1 d U
H20 H 0.7603 -0.4679 0.7648 0.029 Uiso 1 1 calc R
C21 C 0.7657(2) -0.28022(14) 0.82625(14) 0.0204(3) Uani 1 1 d U
H21 H 0.7219 -0.3022 0.9211 0.024 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
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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
C3 O2 B 125.52(10)
C6 N7 C8 118.73(11)
C5 N14 C13 119.91(11)
C5 N14 B 120.24(11)
C13 N14 B 119.79(11)
F2 B F1 110.21(11)
F2 B O2 108.32(11)
F1 B O2 109.87(11)
F2 B N14 109.41(11)
F1 B N14 108.36(11)
O2 B N14 110.65(11)
O2 C3 C4 120.93(12)
O2 C3 C16 114.08(11)
C4 C3 C16 124.98(12)
C3 C4 C5 122.01(12)
C3 C4 H4 119
C5 C4 H4 119
N14 C5 C4 120.24(12)
N14 C5 C6 119.05(11)
C4 C5 C6 120.71(12)
N7 C6 C5 121.83(12)
N7 C6 C15 118.01(12)
C5 C6 C15 120.15(11)
N7 C8 C9 118.29(12)
N7 C8 C13 122.28(12)
C9 C8 C13 119.40(13)
C10 C9 C8 120.39(13)
C10 C9 H9 119.8
C8 C9 H9 119.8
C9 C10 C11 119.88(13)
C9 C10 H10 120.1
C11 C10 H10 120.1
C12 C11 C10 121.27(13)
C12 C11 H11 119.4
C10 C11 H11 119.4
C11 C12 C13 119.45(13)
C11 C12 H12 120.3
C13 C12 H12 120.3
N14 C13 C12 122.33(12)
N14 C13 C8 118.08(12)
C12 C13 C8 119.60(12)
C6 C15 H15A 109.5
C6 C15 H15B 109.5
H15A C15 H15B 109.5
C6 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C21 C16 C17 118.82(12)
C21 C16 C3 121.92(12)
C17 C16 C3 119.26(12)
C18 C17 C16 120.41(13)
C18 C17 H17 119.8
C16 C17 H17 119.8
C19 C18 C17 120.08(13)
C19 C18 H18 120
C17 C18 H18 120
C18 C19 C20 120.34(13)
C18 C19 H19 119.8
C20 C19 H19 119.8
C19 C20 C21 119.81(13)
C19 C20 H20 120.1
C21 C20 H20 120.1
C20 C21 C16 120.54(13)
C20 C21 H21 119.7
C16 C21 H21 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 B 1.3829(17)
F2 B 1.3827(17)
O2 C3 1.3271(15)
O2 B 1.4551(17)
N7 C6 1.3046(16)
N7 C8 1.3720(17)
N14 C5 1.3501(17)
N14 C13 1.3939(16)
N14 B 1.5912(18)
C3 C4 1.3589(18)
C3 C16 1.4799(18)
C4 C5 1.4212(18)
C4 H4 0.95
C5 C6 1.4559(18)
C6 C15 1.4983(18)
C8 C9 1.4101(18)
C8 C13 1.4113(18)
C9 C10 1.365(2)
C9 H9 0.95
C10 C11 1.404(2)
C10 H10 0.95
C11 C12 1.3745(19)
C11 H11 0.95
C12 C13 1.4052(19)
C12 H12 0.95
C15 H15A 0.98
C15 H15B 0.98
C15 H15C 0.98
C16 C21 1.3968(19)
C16 C17 1.3983(18)
C17 C18 1.3887(19)
C17 H17 0.95
C18 C19 1.380(2)
C18 H18 0.95
C19 C20 1.387(2)
C19 H19 0.95
C20 C21 1.3891(19)
C20 H20 0.95
C21 H21 0.95
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 O2 B F2 127.04(12)
C3 O2 B F1 -112.51(13)
C3 O2 B N14 7.11(17)
C5 N14 B F2 -126.05(12)
C13 N14 B F2 56.49(15)
C5 N14 B F1 113.75(13)
C13 N14 B F1 -63.70(14)
C5 N14 B O2 -6.78(16)
C13 N14 B O2 175.77(10)
B O2 C3 C4 -4.16(19)
B O2 C3 C16 175.88(11)
O2 C3 C4 C5 0.0(2)
C16 C3 C4 C5 179.92(11)
C13 N14 C5 C4 -178.81(11)
B N14 C5 C4 3.74(17)
C13 N14 C5 C6 1.49(17)
B N14 C5 C6 -175.96(10)
C3 C4 C5 N14 -0.05(19)
C3 C4 C5 C6 179.64(11)
C8 N7 C6 C5 2.57(18)
C8 N7 C6 C15 -176.12(11)
N14 C5 C6 N7 -3.74(18)
C4 C5 C6 N7 176.56(11)
N14 C5 C6 C15 174.92(11)
C4 C5 C6 C15 -4.78(18)
C6 N7 C8 C9 178.63(11)
C6 N7 C8 C13 0.68(18)
N7 C8 C9 C10 -176.77(12)
C13 C8 C9 C10 1.24(19)
C8 C9 C10 C11 -0.5(2)
C9 C10 C11 C12 -0.4(2)
C10 C11 C12 C13 0.4(2)
C5 N14 C13 C12 -177.97(12)
B N14 C13 C12 -0.51(18)
C5 N14 C13 C8 1.55(17)
B N14 C13 C8 179.01(11)
C11 C12 C13 N14 179.89(12)
C11 C12 C13 C8 0.38(19)
N7 C8 C13 N14 -2.79(18)
C9 C8 C13 N14 179.28(11)
N7 C8 C13 C12 176.74(12)
C9 C8 C13 C12 -1.19(19)
O2 C3 C16 C21 -175.60(11)
C4 C3 C16 C21 4.4(2)
O2 C3 C16 C17 3.74(17)
C4 C3 C16 C17 -176.21(12)
C21 C16 C17 C18 -0.7(2)
C3 C16 C17 C18 179.95(11)
C16 C17 C18 C19 0.6(2)
C17 C18 C19 C20 -0.2(2)
C18 C19 C20 C21 -0.2(2)
C19 C20 C21 C16 0.1(2)
C17 C16 C21 C20 0.34(19)
C3 C16 C21 C20 179.68(12)
