#------------------------------------------------------------------------------
#$Date: 2016-03-26 12:56:19 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180217 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/03/7110345.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_7110345
loop_
_publ_author_name
'Hui Liu'
'Hua Lu'
'Jing Xu'
'Zhipeng Liu'
'Zhifang Li'
'John Mack'
'Zhen Shen'
_publ_section_title
;
 Boron-pyridyl-imino-isoindoline dyes: facile synthesis and photophysical
 properties
;
_journal_name_full               Chem.Commun.
_journal_page_first              1074
_journal_paper_doi               10.1039/c3cc48316a
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C17 H10 B F2 N3 O'
_chemical_formula_weight         321.09
_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                 106.164(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.575(2)
_cell_length_b                   12.611(3)
_cell_length_c                   13.588(3)
_cell_measurement_temperature    296(2)
_cell_volume                     1411.3(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9279
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.114
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.256
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3203
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.256
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0397
_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)+(0.0563P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1150
_reflns_number_gt                2456
_reflns_number_total             3203
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc48316a.txt
_cod_data_source_block           mo_20130701b_0m
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7110345
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
O1 O 0.94713(13) 0.05929(9) 0.24701(7) 0.0540(3) Uani 1 1 d .
F1 F 0.63491(12) 0.19760(6) 0.21962(6) 0.0516(3) Uani 1 1 d .
F2 F 0.81343(11) 0.28878(7) 0.15502(6) 0.0515(3) Uani 1 1 d .
C2 C 0.49396(18) 0.39702(11) 0.15125(10) 0.0401(3) Uani 1 1 d .
H2 H 0.5786 0.3732 0.2057 0.048 Uiso 1 1 calc R
C7 C 0.30185(17) 0.33509(12) -0.12344(10) 0.0423(3) Uani 1 1 d .
H7 H 0.2218 0.3616 -0.1790 0.051 Uiso 1 1 calc R
C8 C 0.38540(17) 0.24743(12) -0.13478(9) 0.0406(3) Uani 1 1 d .
H8 H 0.3626 0.2140 -0.1982 0.049 Uiso 1 1 calc R
N2 N 0.57824(13) 0.11248(9) -0.07057(7) 0.0360(3) Uani 1 1 d .
C12 C 0.76183(18) -0.10024(11) -0.08456(11) 0.0433(3) Uani 1 1 d .
H12 H 0.6865 -0.0894 -0.1478 0.052 Uiso 1 1 calc R
N1 N 0.54729(12) 0.25538(8) 0.04112(7) 0.0301(2) Uani 1 1 d .
C16 C 0.88690(16) -0.04673(10) 0.09062(10) 0.0378(3) Uani 1 1 d .
C14 C 0.9779(2) -0.20270(12) 0.02737(14) 0.0535(4) Uani 1 1 d .
H14 H 1.0467 -0.2611 0.0367 0.064 Uiso 1 1 calc R
C5 C 0.2444(2) 0.47506(12) -0.01119(12) 0.0484(4) Uani 1 1 d .
H5 H 0.1626 0.5024 -0.0653 0.058 Uiso 1 1 calc R
C11 C 0.77517(16) -0.03029(10) -0.00389(10) 0.0351(3) Uani 1 1 d .
C4 C 0.2756(2) 0.52060(13) 0.08357(12) 0.0531(4) Uani 1 1 d .
H4 H 0.2134 0.5776 0.0942 0.064 Uiso 1 1 calc R
C3 C 0.4011(2) 0.48135(12) 0.16444(11) 0.0485(4) Uani 1 1 d .
H3 H 0.4221 0.5132 0.2286 0.058 Uiso 1 1 calc R
N3 N 0.74767(13) 0.10926(9) 0.10017(7) 0.0339(3) Uani 1 1 d .
C15 C 0.99036(19) -0.13306(12) 0.10844(12) 0.0490(4) Uani 1 1 d .
H15 H 1.0650 -0.1440 0.1719 0.059 Uiso 1 1 calc R
C9 C 0.50715(15) 0.20604(10) -0.05119(9) 0.0325(3) Uani 1 1 d .
C13 C 0.8658(2) -0.18734(12) -0.06698(13) 0.0509(4) Uani 1 1 d .
H13 H 0.8599 -0.2359 -0.1194 0.061 Uiso 1 1 calc R
C1 C 0.46113(16) 0.34617(10) 0.05507(9) 0.0323(3) Uani 1 1 d .
B1 B 0.69222(19) 0.21388(12) 0.13547(10) 0.0341(3) Uani 1 1 d .
C17 C 0.87192(16) 0.04267(11) 0.15931(10) 0.0380(3) Uani 1 1 d .
C6 C 0.33546(16) 0.38674(10) -0.02749(10) 0.0368(3) Uani 1 1 d .
C10 C 0.68928(15) 0.06958(10) 0.00350(9) 0.0322(3) 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'
B B 0.0013 0.0007 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 C2 C1 120.02(12)
C3 C2 H2 120.0
C1 C2 H2 120.0
C8 C7 C6 120.30(11)
C8 C7 H7 119.9
C6 C7 H7 119.9
C7 C8 C9 120.56(12)
C7 C8 H8 119.7
C9 C8 H8 119.7
C10 N2 C9 118.35(10)
C11 C12 C13 117.26(13)
C11 C12 H12 121.4
C13 C12 H12 121.4
C9 N1 C1 119.45(10)
C9 N1 B1 122.01(10)
C1 N1 B1 118.54(10)
C15 C16 C11 121.59(13)
C15 C16 C17 130.42(12)
C11 C16 C17 107.98(11)
C13 C14 C15 121.70(14)
C13 C14 H14 119.1
C15 C14 H14 119.1
C4 C5 C6 120.49(13)
C4 C5 H5 119.8
C6 C5 H5 119.8
C12 C11 C16 121.36(13)
C12 C11 C10 131.56(12)
C16 C11 C10 107.07(11)
C5 C4 C3 119.85(14)
C5 C4 H4 120.1
C3 C4 H4 120.1
C2 C3 C4 121.38(13)
C2 C3 H3 119.3
C4 C3 H3 119.3
C10 N3 C17 110.18(11)
C10 N3 B1 123.89(10)
C17 N3 B1 125.83(10)
C16 C15 C14 117.07(14)
C16 C15 H15 121.5
C14 C15 H15 121.5
N1 C9 N2 123.66(10)
N1 C9 C8 121.01(12)
N2 C9 C8 115.32(10)
C14 C13 C12 121.02(15)
C14 C13 H13 119.5
C12 C13 H13 119.5
N1 C1 C2 121.24(11)
N1 C1 C6 120.02(11)
C2 C1 C6 118.72(12)
F2 B1 F1 111.51(11)
F2 B1 N3 111.73(12)
F1 B1 N3 110.25(11)
F2 B1 N1 107.83(10)
F1 B1 N1 109.59(12)
N3 B1 N1 105.72(9)
O1 C17 N3 124.64(13)
O1 C17 C16 129.39(13)
N3 C17 C16 105.97(10)
C5 C6 C7 121.89(12)
C5 C6 C1 119.48(12)
C7 C6 C1 118.60(12)
N2 C10 N3 126.03(12)
N2 C10 C11 125.17(11)
N3 C10 C11 108.79(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C17 1.2051(15)
F1 B1 1.3799(17)
F2 B1 1.3745(17)
C2 C3 1.370(2)
C2 C1 1.4119(17)
C2 H2 0.9300
C7 C8 1.349(2)
C7 C6 1.4134(19)
C7 H7 0.9300
C8 C9 1.4115(17)
C8 H8 0.9300
N2 C10 1.2957(15)
N2 C9 1.3865(16)
C12 C11 1.3867(19)
C12 C13 1.393(2)
C12 H12 0.9300
N1 C9 1.3560(15)
N1 C1 1.4038(17)
N1 B1 1.6047(16)
C16 C15 1.383(2)
C16 C11 1.3876(18)
C16 C17 1.492(2)
C14 C13 1.385(2)
C14 C15 1.390(2)
C14 H14 0.9300
C5 C4 1.367(2)
C5 C6 1.413(2)
C5 H5 0.9300
C11 C10 1.4764(18)
C4 C3 1.398(2)
C4 H4 0.9300
C3 H3 0.9300
N3 C10 1.3640(15)
N3 C17 1.4176(16)
N3 B1 1.5244(19)
C15 H15 0.9300
C13 H13 0.9300
C1 C6 1.4172(17)
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
C6 C7 C8 C9 0.1(2)
C13 C12 C11 C16 -0.4(2)
C13 C12 C11 C10 178.17(14)
C15 C16 C11 C12 0.4(2)
C17 C16 C11 C12 179.23(13)
C15 C16 C11 C10 -178.48(13)
C17 C16 C11 C10 0.38(15)
C6 C5 C4 C3 1.6(3)
C1 C2 C3 C4 -1.6(2)
C5 C4 C3 C2 -0.5(3)
C11 C16 C15 C14 0.2(2)
C17 C16 C15 C14 -178.41(14)
C13 C14 C15 C16 -0.7(2)
C1 N1 C9 N2 -175.90(12)
B1 N1 C9 N2 4.69(19)
C1 N1 C9 C8 3.06(19)
B1 N1 C9 C8 -176.35(12)
C10 N2 C9 N1 -0.01(19)
C10 N2 C9 C8 -179.02(13)
C7 C8 C9 N1 -2.5(2)
C7 C8 C9 N2 176.51(13)
C15 C14 C13 C12 0.7(3)
C11 C12 C13 C14 -0.2(2)
C9 N1 C1 C2 177.01(12)
B1 N1 C1 C2 -3.56(18)
C9 N1 C1 C6 -1.22(18)
B1 N1 C1 C6 178.21(12)
C3 C2 C1 N1 -175.80(13)
C3 C2 C1 C6 2.5(2)
C10 N3 B1 F2 -111.84(13)
C17 N3 B1 F2 64.19(17)
C10 N3 B1 F1 123.56(13)
C17 N3 B1 F1 -60.41(17)
C10 N3 B1 N1 5.19(17)
C17 N3 B1 N1 -178.77(11)
C9 N1 B1 F2 113.00(13)
C1 N1 B1 F2 -66.41(15)
C9 N1 B1 F1 -125.44(12)
C1 N1 B1 F1 55.14(14)
C9 N1 B1 N3 -6.64(17)
C1 N1 B1 N3 173.95(11)
C10 N3 C17 O1 178.68(14)
B1 N3 C17 O1 2.2(2)
C10 N3 C17 C16 -0.87(14)
B1 N3 C17 C16 -177.36(12)
C15 C16 C17 O1 -0.5(3)
C11 C16 C17 O1 -179.25(15)
C15 C16 C17 N3 178.99(14)
C11 C16 C17 N3 0.27(15)
C4 C5 C6 C7 177.31(15)
C4 C5 C6 C1 -0.7(2)
C8 C7 C6 C5 -176.34(14)
C8 C7 C6 C1 1.7(2)
N1 C1 C6 C5 176.94(12)
C2 C1 C6 C5 -1.3(2)
N1 C1 C6 C7 -1.1(2)
C2 C1 C6 C7 -179.42(13)
C9 N2 C10 N3 -1.8(2)
C9 N2 C10 C11 179.16(12)
C17 N3 C10 N2 -178.09(13)
B1 N3 C10 N2 -1.5(2)
C17 N3 C10 C11 1.12(15)
B1 N3 C10 C11 177.70(12)
C12 C11 C10 N2 -0.4(2)
C16 C11 C10 N2 178.29(13)
C12 C11 C10 N3 -179.62(14)
C16 C11 C10 N3 -0.93(15)
