#------------------------------------------------------------------------------
#$Date: 2016-02-05 03:03:33 +0200 (Fri, 05 Feb 2016) $
#$Revision: 176149 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/48/7154818.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_7154818
loop_
_publ_author_name
'Kim, Eunsun'
'Felouat, Abdellah'
'Zaborova, Elena'
'Ribierre, Jean-Charles'
'Wu, Jeong Weon'
'Senatore, Sébastien'
'Matthews, Cédric'
'Lenne, Pierre-François'
'Baffert, Carole'
'Karapetyan, Artak'
'Giorgi, Michel'
'Jacquemin, Denis'
'Ponce-Vargas, Miguel'
'Guennic, Boris Le'
'Fages, Frédéric'
'D'Aléo, Anthony'
_publ_section_title
;
 Borondifluoride complexes of hemicurcuminoids as bio-inspired push-pull
 dyes for bioimaging.
;
_journal_issue                   4
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1311
_journal_page_last               1324
_journal_paper_doi               10.1039/c5ob02295a
_journal_volume                  14
_journal_year                    2016
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C17 H12 B1 F5 O3'
_chemical_formula_sum            'C17 H12 B F5 O3'
_chemical_formula_weight         370.08
_chemical_melting_point          480.1(10)
_chemical_name_systematic
(E)-2,2-difluoro-6-(2-(6-methoxynaphthalen-2-yl)vinyl)-4-(trifluoromethyl)-2H-1,3,2-dioxaborinin-1-ium-2-uide
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2013-05-23T16:43:32-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-10-18 deposited with the CCDC.
2015-12-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 132.732(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.4771(8)
_cell_length_b                   12.8997(8)
_cell_length_c                   15.6366(8)
_cell_measurement_reflns_used    15681
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      3.18
_cell_measurement_wavelength     0.71073
_cell_volume                     3330.2(4)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.142
_diffrn_reflns_av_unetI/netI     0.08
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15681
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.18
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1504
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3394
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.1608
_refine_ls_R_factor_gt           0.0612
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0783P)²+1.0708P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1417
_refine_ls_wR_factor_ref         0.1897
_reflns_number_gt                1519
_reflns_number_total             3394
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c5ob02295a2.cif
_cod_data_source_block           ad801
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '206-208\%C' was changed to
'480.1(10)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7154817--7154821.cif.
;
_cod_original_cell_volume        3330.2(3)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C17 H12 B1 F5 O3'
_cod_database_code               7154818
_audit_block_doi                 10.5517/cc11g2bx
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
C1 C 0.5758(3) -0.0856(4) 0.1816(5) 0.0960(12) Uani 1 1 d .
C2 C 0.6412(2) -0.0150(3) 0.2114(3) 0.0677(9) Uani 1 1 d .
C3 C 0.7119(2) -0.0520(3) 0.2525(3) 0.0732(9) Uani 1 1 d .
H3 H 0.7226 -0.1227 0.265 0.088 Uiso 1 1 calc R
C4 C 0.7694(2) 0.0168(2) 0.2763(3) 0.0658(8) Uani 1 1 d .
C5 C 0.8443(2) -0.0209(3) 0.3149(3) 0.0712(9) Uani 1 1 d .
H5 H 0.8544 -0.0919 0.3256 0.085 Uiso 1 1 calc R
C6 C 0.9000(2) 0.0421(3) 0.3358(3) 0.0703(9) Uani 1 1 d .
H6 H 0.8891 0.1128 0.3276 0.084 Uiso 1 1 calc R
C7 C 0.97597(19) 0.0117(3) 0.3700(3) 0.0638(8) Uani 1 1 d .
C8 C 0.9991(2) -0.0932(3) 0.3840(3) 0.0741(9) Uani 1 1 d .
H8 H 0.966 -0.1452 0.3736 0.089 Uiso 1 1 calc R
C9 C 1.0696(2) -0.1187(2) 0.4128(3) 0.0736(9) Uani 1 1 d .
H9 H 1.084 -0.1882 0.4217 0.088 Uiso 1 1 calc R
C10 C 1.12148(19) -0.0417(2) 0.4293(3) 0.0633(8) Uani 1 1 d .
C11 C 1.1939(2) -0.0669(3) 0.4565(3) 0.0689(9) Uani 1 1 d .
H11 H 1.2097 -0.1358 0.4664 0.083 Uiso 1 1 calc R
C12 C 1.2406(2) 0.0105(3) 0.4680(3) 0.0689(9) Uani 1 1 d .
C13 C 1.2167(2) 0.1148(3) 0.4514(3) 0.0741(9) Uani 1 1 d .
H13 H 1.248 0.1665 0.4567 0.089 Uiso 1 1 calc R
C14 C 1.1485(2) 0.1403(3) 0.4279(3) 0.0731(9) Uani 1 1 d .
H14 H 1.1343 0.2097 0.4198 0.088 Uiso 1 1 calc R
C15 C 1.09854(19) 0.0634(2) 0.4154(2) 0.0618(8) Uani 1 1 d .
C16 C 1.02627(19) 0.0871(3) 0.3875(2) 0.0670(9) Uani 1 1 d .
H16 H 1.0119 0.1563 0.3805 0.08 Uiso 1 1 calc R
C17 C 1.3451(2) -0.1056(3) 0.5245(3) 0.0926(12) Uani 1 1 d .
H17A H 1.3529 -0.1297 0.5896 0.139 Uiso 1 1 calc R
H17B H 1.3962 -0.104 0.5452 0.139 Uiso 1 1 calc R
H17C H 1.3089 -0.1516 0.4597 0.139 Uiso 1 1 calc R
B1 B 0.6776(3) 0.1623(3) 0.2178(4) 0.0754(11) Uani 1 1 d .
F1 F 0.64307(13) 0.21512(17) 0.11832(18) 0.1047(7) Uani 1 1 d .
F2 F 0.69534(13) 0.22666(16) 0.30111(19) 0.1032(7) Uani 1 1 d .
F3 F 0.5949(7) -0.1811(6) 0.2015(19) 0.172(8) Uani 0.63(2) 1 d P
F4 F 0.5098(8) -0.0759(12) 0.0803(8) 0.170(7) Uani 0.63(2) 1 d P
F5 F 0.5605(9) -0.0609(13) 0.2464(13) 0.198(6) Uani 0.63(2) 1 d P
F6 F 0.5471(12) -0.145(2) 0.0860(18) 0.136(7) Uani 0.37(2) 1 d P
F8 F 0.5130(15) -0.0437(13) 0.140(4) 0.237(18) Uani 0.37(2) 1 d P
F7 F 0.5998(13) -0.149(2) 0.2536(15) 0.201(14) Uani 0.37(2) 1 d P
O1 O 0.62139(13) 0.08157(18) 0.1942(2) 0.0872(7) Uani 1 1 d .
O2 O 0.75488(13) 0.11505(16) 0.26177(19) 0.0763(7) Uani 1 1 d .
O3 O 1.31117(14) -0.00364(19) 0.4930(2) 0.0881(7) 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 0 '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'
O O 0.0106 0.006 '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
F7 C1 F4 131.4(9)
F7 C1 F8 115.5(19)
F4 C1 F8 47.1(14)
F7 C1 F3 40.3(14)
F4 C1 F3 108.9(8)
F8 C1 F3 129.9(9)
F7 C1 F5 67.8(15)
F4 C1 F5 104.3(10)
F8 C1 F5 58.9(18)
F3 C1 F5 105.5(9)
F7 C1 F6 102.5(13)
F4 C1 F6 53.4(7)
F8 C1 F6 98.6(14)
F3 C1 F6 63.8(8)
F5 C1 F6 142.2(7)
F7 C1 C2 113.8(9)
F4 C1 C2 113.9(5)
F8 C1 C2 115.7(9)
F3 C1 C2 114.4(6)
F5 C1 C2 109.0(6)
F6 C1 C2 108.2(6)
O1 C2 C3 125.2(3)
O1 C2 C1 113.2(3)
C3 C2 C1 121.7(4)
C2 C3 C4 119.2(3)
C2 C3 H3 120.4
C4 C3 H3 120.4
O2 C4 C3 120.0(3)
O2 C4 C5 119.5(3)
C3 C4 C5 120.6(3)
C6 C5 C4 122.3(3)
C6 C5 H5 118.8
C4 C5 H5 118.8
C5 C6 C7 126.7(3)
C5 C6 H6 116.7
C7 C6 H6 116.7
C16 C7 C8 118.8(3)
C16 C7 C6 119.1(3)
C8 C7 C6 122.1(3)
C9 C8 C7 120.4(3)
C9 C8 H8 119.8
C7 C8 H8 119.8
C8 C9 C10 121.4(3)
C8 C9 H9 119.3
C10 C9 H9 119.3
C11 C10 C15 119.5(3)
C11 C10 C9 122.1(3)
C15 C10 C9 118.4(3)
C12 C11 C10 119.8(3)
C12 C11 H11 120.1
C10 C11 H11 120.1
O3 C12 C11 125.4(3)
O3 C12 C13 113.9(3)
C11 C12 C13 120.7(3)
C14 C13 C12 120.2(3)
C14 C13 H13 119.9
C12 C13 H13 119.9
C13 C14 C15 121.1(3)
C13 C14 H14 119.4
C15 C14 H14 119.4
C16 C15 C14 122.5(3)
C16 C15 C10 118.8(3)
C14 C15 C10 118.7(3)
C7 C16 C15 122.2(3)
C7 C16 H16 118.9
C15 C16 H16 118.9
O3 C17 H17A 109.5
O3 C17 H17B 109.5
H17A C17 H17B 109.5
O3 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
F2 B1 F1 111.1(3)
F2 B1 O1 108.3(3)
F1 B1 O1 109.9(3)
F2 B1 O2 108.4(3)
F1 B1 O2 108.3(3)
O1 B1 O2 110.9(3)
F7 F3 C1 64.4(13)
F7 F3 F6 123.8(19)
C1 F3 F6 62.2(7)
F8 F4 F6 131(2)
F8 F4 C1 64.9(15)
F6 F4 C1 69.9(9)
F7 F5 C1 51.8(7)
F7 F5 F8 100.1(11)
C1 F5 F8 56.5(8)
F4 F6 F3 103.2(11)
F4 F6 C1 56.7(7)
F3 F6 C1 54.0(6)
F4 F8 C1 68.0(10)
F4 F8 F5 130(2)
C1 F8 F5 64.7(16)
F3 F7 C1 75.3(12)
F3 F7 F5 131(2)
C1 F7 F5 60.4(12)
C2 O1 B1 120.9(3)
C4 O2 B1 123.9(3)
C12 O3 C17 117.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 F7 1.186(12)
C1 F4 1.239(9)
C1 F8 1.210(15)
C1 F3 1.273(9)
C1 F5 1.312(10)
C1 F6 1.391(13)
C1 C2 1.508(5)
C2 O1 1.288(4)
C2 C3 1.335(4)
C3 C4 1.395(4)
C3 H3 0.93
C4 O2 1.291(3)
C4 C5 1.434(4)
C5 C6 1.333(4)
C5 H5 0.93
C6 C7 1.455(4)
C6 H6 0.93
C7 C16 1.371(4)
C7 C8 1.412(4)
C8 C9 1.362(5)
C8 H8 0.93
C9 C10 1.416(4)
C9 H9 0.93
C10 C11 1.413(4)
C10 C15 1.414(4)
C11 C12 1.369(4)
C11 H11 0.93
C12 O3 1.363(4)
C12 C13 1.407(4)
C13 C14 1.353(4)
C13 H13 0.93
C14 C15 1.409(4)
C14 H14 0.93
C15 C16 1.400(4)
C16 H16 0.93
C17 O3 1.430(4)
C17 H17A 0.96
C17 H17B 0.96
C17 H17C 0.96
B1 F2 1.357(4)
B1 F1 1.359(4)
B1 O1 1.479(4)
B1 O2 1.497(5)
F3 F7 0.85(3)
F3 F6 1.412(15)
F4 F8 0.98(3)
F4 F6 1.190(13)
F5 F7 1.40(3)
F5 F8 1.24(4)
