# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ad783
_audit_block_doi                 10.5517/cc11g29w
_database_code_depnum_ccdc_archive 'CCDC 966837'
_audit_update_record             
;
2015-10-18 deposited with the CCDC.
2015-12-01 downloaded from the CCDC.
;

_audit_creation_date             2013-04-04T14:34:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
(1E,4Z)-1-(9-ethyl-9H-carbazol-3-yl)-6,6,6-trifluoro-5-hydroxyhexa-1,4-dien-3-one
_chemical_formula_moiety         'C20 H16 F3 N1 O2'
_chemical_formula_sum            'C20 H16 F3 N1 O2'
_chemical_formula_weight         359.34
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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'

_cell_length_a                   7.2632(2)
_cell_length_b                   14.5322(4)
_cell_length_c                   16.5698(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.431(1)
_cell_angle_gamma                90
_cell_volume                     1748.40(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    16427
_cell_measurement_theta_min      1.86
_cell_measurement_theta_max      29.02
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.11
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.059
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_number            16427
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         29.02
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.954
_reflns_number_total             4436
_reflns_number_gt                2462
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1028P)²+0.4701P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4436
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1311
_refine_ls_R_factor_gt           0.0676
_refine_ls_wR_factor_ref         0.2309
_refine_ls_wR_factor_gt          0.1843
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.067

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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_
_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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1386(4) -0.1684(2) 0.06224(18) 0.0786(8) Uani 1 1 d . . .
C2 C 0.1202(4) -0.18321(19) 0.15215(16) 0.0626(6) Uani 1 1 d . . .
C3 C 0.1623(3) -0.11196(18) 0.20482(15) 0.0588(6) Uani 1 1 d . . .
H3 H 0.1965 -0.0551 0.1841 0.071 Uiso 1 1 calc R . .
C4 C 0.1548(3) -0.12329(16) 0.28738(14) 0.0524(6) Uani 1 1 d . . .
C5 C 0.2040(3) -0.05213(18) 0.34375(15) 0.0577(6) Uani 1 1 d . . .
H5 H 0.2421 0.0042 0.3235 0.069 Uiso 1 1 calc R . .
C6 C 0.1984(3) -0.06216(17) 0.42371(15) 0.0553(6) Uani 1 1 d . . .
H6 H 0.1593 -0.1192 0.442 0.066 Uiso 1 1 calc R . .
C7 C 0.2460(3) 0.00501(16) 0.48550(14) 0.0522(6) Uani 1 1 d . . .
C8 C 0.2370(3) -0.02129(16) 0.56596(14) 0.0516(6) Uani 1 1 d . . .
H8 H 0.2005 -0.0807 0.5791 0.062 Uiso 1 1 calc R . .
C9 C 0.2823(3) 0.04069(15) 0.62631(14) 0.0495(5) Uani 1 1 d . . .
C10 C 0.2867(3) 0.03546(17) 0.71362(15) 0.0550(6) Uani 1 1 d . . .
C11 C 0.2448(4) -0.0329(2) 0.76835(16) 0.0710(7) Uani 1 1 d . . .
H11 H 0.2056 -0.0905 0.7506 0.085 Uiso 1 1 calc R . .
C12 C 0.2625(5) -0.0139(3) 0.84965(18) 0.0882(10) Uani 1 1 d . . .
H12 H 0.2347 -0.0594 0.8869 0.106 Uiso 1 1 calc R . .
C13 C 0.3205(5) 0.0710(3) 0.87689(19) 0.0871(10) Uani 1 1 d . . .
H13 H 0.3312 0.0816 0.9322 0.105 Uiso 1 1 calc R . .
C14 C 0.3627(4) 0.1406(2) 0.82424(18) 0.0774(9) Uani 1 1 d . . .
H14 H 0.4017 0.1979 0.843 0.093 Uiso 1 1 calc R . .
C15 C 0.3452(3) 0.12223(19) 0.74166(16) 0.0600(6) Uani 1 1 d . . .
C16 C 0.3388(3) 0.13047(16) 0.60625(15) 0.0526(6) Uani 1 1 d . . .
C17 C 0.3466(3) 0.15816(18) 0.52598(16) 0.0628(7) Uani 1 1 d . . .
H17 H 0.382 0.2176 0.5127 0.075 Uiso 1 1 calc R . .
C18 C 0.3007(3) 0.09563(18) 0.46713(16) 0.0606(6) Uani 1 1 d . . .
H18 H 0.3058 0.1134 0.4133 0.073 Uiso 1 1 calc R . .
C19 C 0.4430(4) 0.27349(19) 0.6796(2) 0.0772(8) Uani 1 1 d . . .
H19A H 0.5218 0.2844 0.6342 0.093 Uiso 1 1 calc R . .
H19B H 0.517 0.2818 0.7287 0.093 Uiso 1 1 calc R . .
C20 C 0.2906(5) 0.3436(2) 0.6780(3) 0.1061(13) Uani 1 1 d . . .
H20A H 0.2141 0.3346 0.6306 0.159 Uiso 1 1 calc R . .
H20B H 0.3425 0.4043 0.6773 0.159 Uiso 1 1 calc R . .
H20C H 0.2178 0.3365 0.7252 0.159 Uiso 1 1 calc R . .
N1 N 0.3776(3) 0.17897(15) 0.67623(13) 0.0609(6) Uani 1 1 d . . .
O1 O 0.0695(4) -0.26196(15) 0.17266(13) 0.0879(7) Uani 1 1 d . . .
O2 O 0.1017(3) -0.20284(13) 0.31746(12) 0.0738(6) Uani 1 1 d . . .
H2O H 0.060(5) -0.240(3) 0.271(2) 0.111 Uiso 1 1 calc R . .
F1 F 0.2839(3) -0.2119(2) 0.03570(14) 0.1377(10) Uani 1 1 d . . .
F2 F -0.0017(3) -0.2002(2) 0.02078(12) 0.1370(10) Uani 1 1 d . . .
F3 F 0.1573(5) -0.08279(18) 0.04224(12) 0.1509(12) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 F3 1.296(4) . ?
C1 F2 1.300(4) . ?
C1 F1 1.315(4) . ?
C1 C2 1.514(4) . ?
C2 O1 1.252(3) . ?
C2 C3 1.384(4) . ?
C3 C4 1.380(3) . ?
C3 H3 0.93 . ?
C4 O2 1.320(3) . ?
C4 C5 1.433(3) . ?
C5 C6 1.335(3) . ?
C5 H5 0.93 . ?
C6 C7 1.450(3) . ?
C6 H6 0.93 . ?
C7 C8 1.390(3) . ?
C7 C18 1.411(3) . ?
C8 C9 1.379(3) . ?
C8 H8 0.93 . ?
C9 C16 1.410(3) . ?
C9 C10 1.448(3) . ?
C10 C11 1.384(4) . ?
C10 C15 1.406(4) . ?
C11 C12 1.378(4) . ?
C11 H11 0.93 . ?
C12 C13 1.377(5) . ?
C12 H12 0.93 . ?
C13 C14 1.375(5) . ?
C13 H13 0.93 . ?
C14 C15 1.397(4) . ?
C14 H14 0.93 . ?
C15 N1 1.387(3) . ?
C16 N1 1.380(3) . ?
C16 C17 1.392(4) . ?
C17 C18 1.368(4) . ?
C17 H17 0.93 . ?
C18 H18 0.93 . ?
C19 N1 1.454(3) . ?
C19 C20 1.504(4) . ?
C19 H19A 0.97 . ?
C19 H19B 0.97 . ?
C20 H20A 0.96 . ?
C20 H20B 0.96 . ?
C20 H20C 0.96 . ?
O2 H2O 0.99(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F3 C1 F2 107.0(3) . . ?
F3 C1 F1 106.6(3) . . ?
F2 C1 F1 106.1(3) . . ?
F3 C1 C2 113.6(2) . . ?
F2 C1 C2 112.5(3) . . ?
F1 C1 C2 110.6(3) . . ?
O1 C2 C3 125.1(3) . . ?
O1 C2 C1 115.5(2) . . ?
C3 C2 C1 119.4(3) . . ?
C4 C3 C2 121.5(2) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
O2 C4 C3 119.9(2) . . ?
O2 C4 C5 117.2(2) . . ?
C3 C4 C5 123.0(2) . . ?
C6 C5 C4 123.7(2) . . ?
C6 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
C5 C6 C7 127.9(2) . . ?
C5 C6 H6 116 . . ?
C7 C6 H6 116 . . ?
C8 C7 C18 118.9(2) . . ?
C8 C7 C6 118.4(2) . . ?
C18 C7 C6 122.6(2) . . ?
C9 C8 C7 120.0(2) . . ?
C9 C8 H8 120 . . ?
C7 C8 H8 120 . . ?
C8 C9 C16 119.9(2) . . ?
C8 C9 C10 133.5(2) . . ?
C16 C9 C10 106.5(2) . . ?
C11 C10 C15 119.8(2) . . ?
C11 C10 C9 133.8(2) . . ?
C15 C10 C9 106.4(2) . . ?
C12 C11 C10 118.7(3) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C13 C12 C11 121.4(3) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C14 C13 C12 121.5(3) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 117.7(3) . . ?
C13 C14 H14 121.2 . . ?
C15 C14 H14 121.2 . . ?
N1 C15 C14 129.7(3) . . ?
N1 C15 C10 109.3(2) . . ?
C14 C15 C10 121.0(3) . . ?
N1 C16 C17 130.0(2) . . ?
N1 C16 C9 109.2(2) . . ?
C17 C16 C9 120.8(2) . . ?
C18 C17 C16 118.3(2) . . ?
C18 C17 H17 120.8 . . ?
C16 C17 H17 120.8 . . ?
C17 C18 C7 122.1(2) . . ?
C17 C18 H18 119 . . ?
C7 C18 H18 119 . . ?
N1 C19 C20 113.5(2) . . ?
N1 C19 H19A 108.9 . . ?
C20 C19 H19A 108.9 . . ?
N1 C19 H19B 108.9 . . ?
C20 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 N1 C15 108.6(2) . . ?
C16 N1 C19 125.1(2) . . ?
C15 N1 C19 126.4(2) . . ?
C4 O2 H2O 106(2) . . ?

# END of CIF
_chemical_melting_point          95-97\%C
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethylacetate'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ad801
_audit_block_doi                 10.5517/cc11g2bx
_database_code_depnum_ccdc_archive 'CCDC 966838'
_audit_update_record             
;
2015-10-18 deposited with the CCDC.
2015-12-01 downloaded from the CCDC.
;

_audit_creation_date             2013-05-23T16:43:32-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_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
_chemical_formula_moiety         'C17 H12 B1 F5 O3'
_chemical_formula_sum            'C17 H12 B1 F5 O3'
_chemical_formula_weight         370.08
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
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'

_cell_length_a                   22.4771(8)
_cell_length_b                   12.8997(8)
_cell_length_c                   15.6366(8)
_cell_angle_alpha                90
_cell_angle_beta                 132.732(5)
_cell_angle_gamma                90
_cell_volume                     3330.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    15681
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      26.37
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1504
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.142
_diffrn_reflns_av_unetI/netI     0.08
_diffrn_reflns_number            15681
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.18
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             3394
_reflns_number_gt                1519
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0783P)²+1.0708P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3394
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1608
_refine_ls_R_factor_gt           0.0612
_refine_ls_wR_factor_ref         0.1897
_refine_ls_wR_factor_gt          0.1417
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_restrained_S_all      1.03
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.038

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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_
_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
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
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) . . ?

# END of CIF
_chemical_melting_point          206-208\%C
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ad762
_audit_block_doi                 10.5517/cc11g2cy
_database_code_depnum_ccdc_archive 'CCDC 966839'
_audit_update_record             
;
2015-10-18 deposited with the CCDC.
2015-12-01 downloaded from the CCDC.
;

_audit_creation_date             2013-10-07T14:33:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
(E)-2,2-difluoro-4-isobutyl-6-(2-(pyren-1-yl)vinyl)-2H-1,3,2-dioxaborinin-1-ium-2-uide
_chemical_formula_moiety         'C25 H21 B1 F2 O2'
_chemical_formula_sum            'C25 H21 B1 F2 O2'
_chemical_formula_weight         402.23
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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'

_cell_length_a                   11.5387(4)
_cell_length_b                   9.8453(4)
_cell_length_c                   19.8519(9)
_cell_angle_alpha                90
_cell_angle_beta                 117.760(1)
_cell_angle_gamma                90
_cell_volume                     1995.65(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    19127
_cell_measurement_theta_min      2.246
_cell_measurement_theta_max      29.022
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  0.992

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0840
_diffrn_reflns_number            19127
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.246
_diffrn_reflns_theta_max         29.022
_diffrn_reflns_theta_full        26
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.965
_reflns_number_total             5138
_reflns_number_gt                2092
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1198P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5138
_refine_ls_number_parameters     271
_refine_ls_number_restraints     12
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.2017
_refine_ls_R_factor_gt           0.0796
_refine_ls_wR_factor_ref         0.2477
_refine_ls_wR_factor_gt          0.2015
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.47
_refine_diff_density_rms         0.05

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
O O 0.0106 0.006 '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_
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1023(4) -0.1274(3) -1.11826(19) 0.0717(9) Uani 1 d . .
H1A H -0.1871 -0.0833 -1.1443 0.086 Uiso 1 calc . .
H1B H -0.0381 -0.057 -1.092 0.086 Uiso 1 calc . .
C2 C -0.1051(3) -0.2196(3) -1.06020(17) 0.0545(7) Uani 1 d . .
C3 C -0.2108(3) -0.2995(3) -1.07318(17) 0.0587(8) Uani 1 d . .
H3 H -0.2871 -0.2924 -1.1192 0.07 Uiso 1 calc . .
C4 C -0.2057(3) -0.3903(2) -1.01896(17) 0.0494(7) Uani 1 d . .
C5 C -0.3142(3) -0.4803(3) -1.03448(17) 0.0582(8) Uani 1 d . .
H5 H -0.387 -0.4765 -1.0823 0.07 Uiso 1 calc . .
C6 C -0.3156(3) -0.5679(3) -0.98430(17) 0.0544(7) Uani 1 d . .
H6 H -0.2422 -0.5685 -0.9367 0.065 Uiso 1 calc . .
C7 C -0.4189(3) -0.6632(2) -0.99537(16) 0.0514(7) Uani 1 d . .
C8 C -0.5247(3) -0.6830(3) -1.06784(18) 0.0608(8) Uani 1 d . .
H8 H -0.5286 -0.6318 -1.1082 0.073 Uiso 1 calc . .
C9 C -0.6230(3) -0.7752(3) -1.08175(18) 0.0630(8) Uani 1 d . .
H9 H -0.6915 -0.7846 -1.1308 0.076 Uiso 1 calc . .
C10 C -0.6208(3) -0.8543(3) -1.02322(17) 0.0532(7) Uani 1 d . .
C11 C -0.7197(3) -0.9529(3) -1.0358(2) 0.0640(8) Uani 1 d . .
H11 H -0.7882 -0.9647 -1.0847 0.077 Uiso 1 calc . .
C12 C -0.7160(3) -1.0290(3) -0.9786(2) 0.0662(9) Uani 1 d . .
H12 H -0.7817 -1.0926 -0.9888 0.079 Uiso 1 calc . .
C13 C -0.6138(3) -1.0143(3) -0.90281(19) 0.0596(8) Uani 1 d . .
C14 C -0.6075(3) -1.0921(3) -0.8421(2) 0.0739(10) Uani 1 d . .
H14 H -0.672 -1.1565 -0.8511 0.089 Uiso 1 calc . .
C15 C -0.5078(4) -1.0748(4) -0.7698(2) 0.0832(11) Uani 1 d . .
H15 H -0.5059 -1.1268 -0.7302 0.1 Uiso 1 calc . .
C16 C -0.4100(3) -0.9808(3) -0.7551(2) 0.0733(9) Uani 1 d . .
H16 H -0.3431 -0.9702 -0.7057 0.088 Uiso 1 calc . .
C17 C -0.4104(3) -0.9019(3) -0.81309(17) 0.0574(8) Uani 1 d . .
C18 C -0.3105(3) -0.8046(3) -0.80006(18) 0.0613(8) Uani 1 d . .
H18 H -0.2415 -0.7943 -0.7512 0.074 Uiso 1 calc . .
C19 C -0.3138(3) -0.7270(3) -0.85728(17) 0.0583(8) Uani 1 d . .
H19 H -0.2479 -0.6633 -0.8463 0.07 Uiso 1 calc . .
C20 C -0.4158(3) -0.7397(2) -0.93446(16) 0.0467(7) Uani 1 d . .
C21 C -0.5169(3) -0.8366(2) -0.94844(17) 0.0495(7) Uani 1 d . .
C22 C -0.5144(3) -0.9168(2) -0.88850(17) 0.0507(7) Uani 1 d . .
C23 C -0.0734(8) -0.1852(4) -1.1741(3) 0.1534(19) Uani 1 d . .
H23 H 0.0217 -0.1809 -1.1424 0.184 Uiso 1 calc . .
C24 C -0.0764(7) -0.0819(4) -1.2330(3) 0.156(2) Uani 1 d . .
H24A H -0.0329 -0.1197 -1.2598 0.234 Uiso 1 calc . .
H24B H -0.0325 -0.0002 -1.2075 0.234 Uiso 1 calc . .
H24C H -0.1656 -0.0615 -1.2685 0.234 Uiso 1 calc . .
C25 C -0.0742(5) -0.3193(4) -1.1940(3) 0.1140(15) Uani 1 d . .
H25A H -0.0464 -0.3753 -1.1495 0.171 Uiso 1 calc . .
H25B H -0.0155 -0.3313 -1.2154 0.171 Uiso 1 calc . .
H25C H -0.1612 -0.3447 -1.2308 0.171 Uiso 1 calc . .
B1 B 0.0101(4) -0.3047(3) -0.9301(2) 0.0609(9) Uani 1 d . .
O1 O -0.0001(2) -0.2221(2) -0.99559(13) 0.0723(7) Uani 1 d . .
O2 O -0.1033(2) -0.3976(2) -0.95352(12) 0.0679(6) Uani 1 d . .
F1 F 0.0122(2) -0.21786(18) -0.87600(11) 0.0867(6) Uani 1 d . .
F2 F 0.12105(18) -0.37821(19) -0.90302(12) 0.0868(6) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C23 1.417(5) . ?
C1 C2 1.479(4) . ?
C1 H1A 0.97 . ?
C1 H1B 0.97 . ?
C2 O1 1.291(3) . ?
C2 C3 1.372(4) . ?
C3 C4 1.379(4) . ?
C3 H3 0.93 . ?
C4 O2 1.288(3) . ?
C4 C5 1.445(4) . ?
C5 C6 1.323(4) . ?
C5 H5 0.93 . ?
C6 C7 1.451(4) . ?
C6 H6 0.93 . ?
C7 C8 1.401(4) . ?
C7 C20 1.411(4) . ?
C8 C9 1.377(4) . ?
C8 H8 0.93 . ?
C9 C10 1.389(4) . ?
C9 H9 0.93 . ?
C10 C21 1.419(4) . ?
C10 C11 1.428(4) . ?
C11 C12 1.344(4) . ?
C11 H11 0.93 . ?
C12 C13 1.422(4) . ?
C12 H12 0.93 . ?
C13 C14 1.401(4) . ?
C13 C22 1.419(4) . ?
C14 C15 1.368(5) . ?
C14 H14 0.93 . ?
C15 C16 1.381(5) . ?
C15 H15 0.93 . ?
C16 C17 1.386(4) . ?
C16 H16 0.93 . ?
C17 C22 1.424(4) . ?
C17 C18 1.427(4) . ?
C18 C19 1.355(4) . ?
C18 H18 0.93 . ?
C19 C20 1.438(4) . ?
C19 H19 0.93 . ?
C20 C21 1.430(4) . ?
C21 C22 1.417(4) . ?
C23 C25 1.377(5) . ?
C23 C24 1.538(5) . ?
C23 H23 0.98 . ?
C24 H24A 0.96 . ?
C24 H24B 0.96 . ?
C24 H24C 0.96 . ?
C25 H25A 0.96 . ?
C25 H25B 0.96 . ?
C25 H25C 0.96 . ?
B1 F2 1.346(4) . ?
B1 F1 1.364(4) . ?
B1 O2 1.483(4) . ?
B1 O1 1.491(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C23 C1 C2 117.4(3) . . ?
C23 C1 H1A 107.9 . . ?
C2 C1 H1A 107.9 . . ?
C23 C1 H1B 107.9 . . ?
C2 C1 H1B 107.9 . . ?
H1A C1 H1B 107.2 . . ?
O1 C2 C3 121.1(3) . . ?
O1 C2 C1 115.8(3) . . ?
C3 C2 C1 123.1(3) . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
O2 C4 C3 120.6(3) . . ?
O2 C4 C5 118.5(2) . . ?
C3 C4 C5 120.9(3) . . ?
C6 C5 C4 123.5(3) . . ?
C6 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
C5 C6 C7 127.2(3) . . ?
C5 C6 H6 116.4 . . ?
C7 C6 H6 116.4 . . ?
C8 C7 C20 117.9(2) . . ?
C8 C7 C6 120.5(3) . . ?
C20 C7 C6 121.6(3) . . ?
C9 C8 C7 122.7(3) . . ?
C9 C8 H8 118.6 . . ?
C7 C8 H8 118.6 . . ?
C8 C9 C10 120.7(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C21 118.9(2) . . ?
C9 C10 C11 122.2(3) . . ?
C21 C10 C11 118.9(3) . . ?
C12 C11 C10 121.5(3) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 121.5(3) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 C13 C22 119.0(3) . . ?
C14 C13 C12 122.7(3) . . ?
C22 C13 C12 118.4(3) . . ?
C15 C14 C13 121.0(3) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 120.6(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C17 120.9(3) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C22 119.4(3) . . ?
C16 C17 C18 122.4(3) . . ?
C22 C17 C18 118.2(3) . . ?
C19 C18 C17 121.4(3) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C20 122.3(3) . . ?
C18 C19 H19 118.9 . . ?
C20 C19 H19 118.9 . . ?
C7 C20 C21 119.8(3) . . ?
C7 C20 C19 123.2(2) . . ?
C21 C20 C19 117.0(2) . . ?
C22 C21 C10 119.1(2) . . ?
C22 C21 C20 120.8(3) . . ?
C10 C21 C20 120.0(3) . . ?
C21 C22 C13 120.7(3) . . ?
C21 C22 C17 120.2(2) . . ?
C13 C22 C17 119.1(3) . . ?
C25 C23 C1 129.6(4) . . ?
C25 C23 C24 114.9(4) . . ?
C1 C23 C24 113.5(3) . . ?
C25 C23 H23 94.7 . . ?
C1 C23 H23 94.7 . . ?
C24 C23 H23 94.7 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
F2 B1 F1 110.9(3) . . ?
F2 B1 O2 109.3(3) . . ?
F1 B1 O2 108.8(3) . . ?
F2 B1 O1 108.4(3) . . ?
F1 B1 O1 108.1(3) . . ?
O2 B1 O1 111.3(3) . . ?
C2 O1 B1 122.2(2) . . ?
C4 O2 B1 122.9(2) . . ?

# END of CIF
_chemical_melting_point          150-152\%C
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethylacetate'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ad759
_audit_block_doi                 10.5517/cc11g2dz
_database_code_depnum_ccdc_archive 'CCDC 966840'
_audit_update_record             
;
2015-10-18 deposited with the CCDC.
2015-12-01 downloaded from the CCDC.
;

_audit_creation_date             2013-10-03T15:28:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
(E)-2,2-difluoro-6-(2-(pyren-1-yl)vinyl)-4-(trifluoromethyl)-2H-1,3,2-dioxaborinin-1-ium-2-uide
_chemical_formula_moiety         'C22.12 H12 B Cl0.38 F5 O2'
_chemical_formula_sum            'C22.12 H12 B Cl0.38 F5 O2'
_chemical_formula_weight         428.92
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
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'

_cell_length_a                   21.523(1)
_cell_length_b                   13.3264(9)
_cell_length_c                   14.604(1)
_cell_angle_alpha                90
_cell_angle_beta                 95.233(7)
_cell_angle_gamma                90
_cell_volume                     4171.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    19024
_cell_measurement_theta_min      2.333
_cell_measurement_theta_max      28.589
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1737
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_T_max  0.987


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_reflns_number            19024
_diffrn_reflns_av_R_equivalents  0.1260
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.333
_diffrn_reflns_theta_max         28.589
_diffrn_reflns_theta_full        26
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.943
_reflns_number_total             5015
_reflns_number_gt                1654
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1735P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5015
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.2664
_refine_ls_R_factor_gt           0.111
_refine_ls_wR_factor_ref         0.3379
_refine_ls_wR_factor_gt          0.2749
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_restrained_S_all      0.922
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.063

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
O O 0.0106 0.006 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3582(4) 0.4466(7) 0.3754(6) 0.136(3) Uani 1 d . .
C2 C 0.2963(3) 0.4178(5) 0.3298(4) 0.1000(18) Uani 1 d . .
C3 C 0.2541(2) 0.4888(4) 0.2992(3) 0.0811(14) Uani 1 d . .
H3 H 0.2636 0.5567 0.3047 0.097 Uiso 1 calc . .
C4 C 0.1958(2) 0.4568(4) 0.2594(3) 0.0690(12) Uani 1 d . .
C5 C 0.1473(2) 0.5263(3) 0.2291(3) 0.0662(12) Uani 1 d . .
H5 H 0.1546 0.5946 0.2379 0.079 Uiso 1 calc . .
C6 C 0.0918(2) 0.4968(3) 0.1887(2) 0.0648(12) Uani 1 d . .
H6 H 0.0856 0.4278 0.1837 0.078 Uiso 1 calc . .
C7 C 0.0408(2) 0.5590(3) 0.1523(2) 0.0620(11) Uani 1 d . .
C8 C 0.0472(2) 0.6643(3) 0.1537(3) 0.0683(12) Uani 1 d . .
H8 H 0.0843 0.6926 0.1794 0.082 Uiso 1 calc . .
C9 C 0.0003(2) 0.7254(3) 0.1182(3) 0.0726(13) Uani 1 d . .
H9 H 0.006 0.7946 0.1203 0.087 Uiso 1 calc . .
C10 C -0.0568(2) 0.6859(3) 0.0783(3) 0.0655(11) Uani 1 d . .
C11 C -0.1051(2) 0.7485(4) 0.0376(3) 0.0798(14) Uani 1 d . .
H11 H -0.0992 0.8176 0.037 0.096 Uiso 1 calc . .
C12 C -0.1590(2) 0.7097(4) -0.0001(3) 0.0815(14) Uani 1 d . .
H12 H -0.1897 0.753 -0.0257 0.098 Uiso 1 calc . .
C13 C -0.1710(2) 0.6043(3) -0.0024(3) 0.0677(12) Uani 1 d . .
C14 C -0.2255(2) 0.5637(4) -0.0402(3) 0.0812(14) Uani 1 d . .
H14 H -0.2572 0.6058 -0.0649 0.097 Uiso 1 calc . .
C15 C -0.2344(3) 0.4613(5) -0.0424(3) 0.0922(16) Uani 1 d . .
H15 H -0.2713 0.4349 -0.0704 0.111 Uiso 1 calc . .
C16 C -0.1898(3) 0.3993(4) -0.0044(3) 0.0816(14) Uani 1 d . .
H16 H -0.1973 0.3306 -0.0048 0.098 Uiso 1 calc . .
C17 C -0.1326(2) 0.4351(4) 0.0357(3) 0.0701(12) Uani 1 d . .
C18 C -0.0841(2) 0.3734(4) 0.0744(3) 0.0720(12) Uani 1 d . .
H18 H -0.09 0.3043 0.0737 0.086 Uiso 1 calc . .
C19 C -0.0292(2) 0.4106(3) 0.1125(3) 0.0720(13) Uani 1 d . .
H19 H 0.0012 0.3666 0.1379 0.086 Uiso 1 calc . .
C20 C -0.0167(2) 0.5158(3) 0.1147(3) 0.0622(11) Uani 1 d . .
C21 C -0.0652(2) 0.5805(3) 0.0767(3) 0.0629(11) Uani 1 d . .
C22 C -0.1230(2) 0.5405(3) 0.0368(3) 0.0679(12) Uani 1 d . .
B1 B 0.2315(4) 0.2813(5) 0.2766(5) 0.099(2) Uani 1 d . .
O1 O 0.2878(2) 0.3224(3) 0.3244(3) 0.1204(15) Uani 1 d . .
O2 O 0.18472(15) 0.3614(2) 0.2489(2) 0.0824(10) Uani 1 d . .
F1 F 0.24668(17) 0.2363(2) 0.1975(2) 0.1249(13) Uani 1 d . .
F2 F 0.20452(19) 0.2176(3) 0.3334(3) 0.1362(14) Uani 1 d . .
F3 F 0.4031(2) 0.4229(4) 0.3215(4) 0.182(2) Uani 1 d . .
F4 F 0.3740(2) 0.3956(4) 0.4510(3) 0.186(2) Uani 1 d . .
F5 F 0.3652(2) 0.5413(4) 0.3946(4) 0.210(3) Uani 1 d . .
C23 C 0.0346(18) 0.176(2) 0.251(2) 0.099(11) Uani 0.175 d . .
Cl1 Cl -0.0115(13) 0.1157(19) 0.1593(15) 0.58(2) Uani 0.35 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 F5 1.299(8) . ?
C1 F4 1.315(9) . ?
C1 F3 1.340(9) . ?
C1 C2 1.484(9) . ?
C2 O1 1.287(6) . ?
C2 C3 1.359(7) . ?
C3 C4 1.399(6) . ?
C3 H3 0.93 . ?
C4 O2 1.300(5) . ?
C4 C5 1.435(6) . ?
C5 C6 1.342(6) . ?
C5 H5 0.93 . ?
C6 C7 1.438(6) . ?
C6 H6 0.93 . ?
C7 C8 1.411(6) . ?
C7 C20 1.430(6) . ?
C8 C9 1.363(6) . ?
C8 H8 0.93 . ?
C9 C10 1.413(6) . ?
C9 H9 0.93 . ?
C10 C21 1.417(6) . ?
C10 C11 1.420(6) . ?
C11 C12 1.343(6) . ?
C11 H11 0.93 . ?
C12 C13 1.427(6) . ?
C12 H12 0.93 . ?
C13 C14 1.362(6) . ?
C13 C22 1.418(6) . ?
C14 C15 1.378(7) . ?
C14 H14 0.93 . ?
C15 C16 1.347(7) . ?
C15 H15 0.93 . ?
C16 C17 1.399(6) . ?
C16 H16 0.93 . ?
C17 C18 1.405(6) . ?
C17 C22 1.420(6) . ?
C18 C19 1.354(6) . ?
C18 H18 0.93 . ?
C19 C20 1.427(6) . ?
C19 H19 0.93 . ?
C20 C21 1.425(6) . ?
C21 C22 1.428(6) . ?
B1 F2 1.356(8) . ?
B1 F1 1.367(7) . ?
B1 O1 1.449(8) . ?
B1 O2 1.498(7) . ?
C23 C23 1.49(8) 2 ?
C23 Cl1 1.65(4) 2 ?
C23 Cl1 1.79(4) . ?
Cl1 C23 1.65(4) 2 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F5 C1 F4 107.8(7) . . ?
F5 C1 F3 106.3(8) . . ?
F4 C1 F3 103.1(6) . . ?
F5 C1 C2 115.4(6) . . ?
F4 C1 C2 113.4(8) . . ?
F3 C1 C2 110.0(7) . . ?
O1 C2 C3 125.5(5) . . ?
O1 C2 C1 113.5(5) . . ?
C3 C2 C1 120.9(6) . . ?
C2 C3 C4 118.2(5) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
O2 C4 C3 119.6(4) . . ?
O2 C4 C5 118.3(4) . . ?
C3 C4 C5 122.1(5) . . ?
C6 C5 C4 122.7(4) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C5 C6 C7 127.7(4) . . ?
C5 C6 H6 116.1 . . ?
C7 C6 H6 116.1 . . ?
C8 C7 C20 119.0(4) . . ?
C8 C7 C6 119.9(4) . . ?
C20 C7 C6 121.1(4) . . ?
C9 C8 C7 121.5(4) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 121.4(4) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C9 C10 C21 118.8(4) . . ?
C9 C10 C11 122.0(4) . . ?
C21 C10 C11 119.2(4) . . ?
C12 C11 C10 121.2(5) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 122.4(5) . . ?
C11 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C14 C13 C22 119.6(5) . . ?
C14 C13 C12 123.2(5) . . ?
C22 C13 C12 117.2(4) . . ?
C13 C14 C15 121.0(5) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C16 C15 C14 120.4(5) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 122.0(5) . . ?
C15 C16 H16 119 . . ?
C17 C16 H16 119 . . ?
C16 C17 C18 124.2(5) . . ?
C16 C17 C22 117.6(5) . . ?
C18 C17 C22 118.2(4) . . ?
C19 C18 C17 122.6(4) . . ?
C19 C18 H18 118.7 . . ?
C17 C18 H18 118.7 . . ?
C18 C19 C20 121.6(4) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C21 C20 C19 117.1(4) . . ?
C21 C20 C7 119.0(4) . . ?
C19 C20 C7 123.9(4) . . ?
C10 C21 C20 120.4(4) . . ?
C10 C21 C22 118.8(4) . . ?
C20 C21 C22 120.8(4) . . ?
C13 C22 C17 119.3(4) . . ?
C13 C22 C21 121.1(4) . . ?
C17 C22 C21 119.6(4) . . ?
F2 B1 F1 113.0(5) . . ?
F2 B1 O1 109.1(5) . . ?
F1 B1 O1 108.7(6) . . ?
F2 B1 O2 107.2(6) . . ?
F1 B1 O2 107.0(5) . . ?
O1 B1 O2 111.9(5) . . ?
C2 O1 B1 120.7(4) . . ?
C4 O2 B1 123.6(4) . . ?
C23 C23 Cl1 69(2) 2 2 ?
C23 C23 Cl1 59.5(19) 2 . ?
Cl1 C23 Cl1 101(2) 2 . ?
C23 Cl1 C23 51(3) 2 . ?

# END of CIF

_chemical_melting_point          223-225\%C
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ad741
_audit_block_doi                 10.5517/cc1k232t
_database_code_depnum_ccdc_archive 'CCDC 1431985'
_audit_update_record             
;
2015-10-18 deposited with the CCDC.
2015-12-01 downloaded from the CCDC.
;

_audit_creation_date             2013-10-01T16:13:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
(E)-2,2-difluoro-6-(4-(methylthio)styryl)-4-phenyl-2H-1,3,2-dioxaborinin-1-ium-2-uide
_chemical_formula_moiety         'C18 H15 B1 F2 O2 S1'
_chemical_formula_sum            'C18 H15 B1 F2 O2 S1'
_chemical_formula_weight         344.17
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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'

_cell_length_a                   8.0580(2)
_cell_length_b                   11.8497(3)
_cell_length_c                   17.4330(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.565(1)
_cell_angle_gamma                90
_cell_volume                     1611.09(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    15748
_cell_measurement_theta_min      3.106
_cell_measurement_theta_max      29.013
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.067
_diffrn_reflns_number            15748
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.106
_diffrn_reflns_theta_max         29.013
_diffrn_reflns_theta_full        26
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.967
_reflns_number_total             4145
_reflns_number_gt                2616
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0537P)²+0.5137P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4145
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1385
_refine_ls_wR_factor_gt          0.1161
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_restrained_S_all      1.04
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.04

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H H 0 0 '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'
O O 0.0106 0.006 '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'
S S 0.1246 0.1234 '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_
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3476(2) -0.09628(16) 0.85035(11) 0.0447(4) Uani 1 d . .
C2 C 0.3670(2) -0.06575(16) 0.77183(11) 0.0457(4) Uani 1 d . .
C3 C 0.4136(3) -0.14839(18) 0.72419(12) 0.0537(5) Uani 1 d . .
H3 H 0.4306 -0.2223 0.7425 0.064 Uiso 1 calc . .
C4 C 0.4346(3) -0.1216(2) 0.65034(13) 0.0623(6) Uani 1 d . .
H4 H 0.4661 -0.1772 0.6191 0.075 Uiso 1 calc . .
C5 C 0.4089(3) -0.0127(2) 0.62277(13) 0.0639(6) Uani 1 d . .
H5 H 0.4227 0.005 0.5728 0.077 Uiso 1 calc . .
C6 C 0.3631(3) 0.0704(2) 0.66873(14) 0.0652(6) Uani 1 d . .
H6 H 0.3461 0.1439 0.6498 0.078 Uiso 1 calc . .
C7 C 0.3421(3) 0.04424(18) 0.74327(13) 0.0563(5) Uani 1 d . .
H7 H 0.3113 0.1004 0.7743 0.068 Uiso 1 calc . .
C8 C 0.3049(2) -0.02299(16) 0.90361(11) 0.0480(4) Uani 1 d . .
H8 H 0.2899 0.0532 0.891 0.058 Uiso 1 calc . .
C9 C 0.2840(2) -0.06106(15) 0.97543(11) 0.0456(4) Uani 1 d . .
C10 C 0.2331(2) 0.01180(16) 1.03147(12) 0.0484(4) Uani 1 d . .
H10 H 0.2081 0.0869 1.0179 0.058 Uiso 1 calc . .
C11 C 0.2207(2) -0.02458(16) 1.10228(11) 0.0467(4) Uani 1 d . .
H11 H 0.247 -0.1002 1.1133 0.056 Uiso 1 calc . .
C12 C 0.1713(2) 0.03880(15) 1.16440(11) 0.0430(4) Uani 1 d . .
C13 C 0.1134(2) 0.15032(16) 1.15544(12) 0.0490(5) Uani 1 d . .
H13 H 0.1042 0.1872 1.1075 0.059 Uiso 1 calc . .
C14 C 0.0700(2) 0.20607(16) 1.21657(12) 0.0507(5) Uani 1 d . .
H14 H 0.0306 0.28 1.2092 0.061 Uiso 1 calc . .
C15 C 0.0837(2) 0.15369(15) 1.28966(11) 0.0447(4) Uani 1 d . .
C16 C 0.1394(2) 0.04220(16) 1.29903(12) 0.0484(4) Uani 1 d . .
H16 H 0.1482 0.0052 1.3469 0.058 Uiso 1 calc . .
C17 C 0.1814(2) -0.01337(16) 1.23682(11) 0.0476(4) Uani 1 d . .
H17 H 0.2176 -0.088 1.2436 0.057 Uiso 1 calc . .
C18 C 0.0428(3) 0.1379(2) 1.44368(14) 0.0760(7) Uani 1 d . .
H18A H -0.0257 0.0727 1.4243 0.114 Uiso 1 calc . .
H18B H 0.0001 0.1735 1.4843 0.114 Uiso 1 calc . .
H18C H 0.1596 0.1152 1.4652 0.114 Uiso 1 calc . .
O1 O 0.3723(2) -0.20272(12) 0.86824(8) 0.0628(4) Uani 1 d . .
O2 O 0.3079(2) -0.16678(11) 0.99537(9) 0.0644(4) Uani 1 d . .
F1 F 0.2684(2) -0.34044(12) 0.93642(8) 0.0864(5) Uani 1 d . .
F2 F 0.53701(19) -0.27648(14) 0.98487(8) 0.0868(5) Uani 1 d . .
S1 S 0.03224(8) 0.23481(5) 1.36425(3) 0.0622(2) Uani 1 d . .
B1 B 0.3727(4) -0.2493(2) 0.94687(14) 0.0555(6) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.303(2) . ?
C1 C8 1.377(3) . ?
C1 C2 1.462(3) . ?
C2 C7 1.392(3) . ?
C2 C3 1.395(3) . ?
C3 C4 1.377(3) . ?
C3 H3 0.93 . ?
C4 C5 1.375(3) . ?
C4 H4 0.93 . ?
C5 C6 1.377(3) . ?
C5 H5 0.93 . ?
C6 C7 1.387(3) . ?
C6 H6 0.93 . ?
C7 H7 0.93 . ?
C8 C9 1.380(3) . ?
C8 H8 0.93 . ?
C9 O2 1.301(2) . ?
C9 C10 1.438(3) . ?
C10 C11 1.335(3) . ?
C10 H10 0.93 . ?
C11 C12 1.453(3) . ?
C11 H11 0.93 . ?
C12 C17 1.390(3) . ?
C12 C13 1.397(3) . ?
C13 C14 1.372(3) . ?
C13 H13 0.93 . ?
C14 C15 1.396(3) . ?
C14 H14 0.93 . ?
C15 C16 1.391(3) . ?
C15 S1 1.7489(19) . ?
C16 C17 1.382(3) . ?
C16 H16 0.93 . ?
C17 H17 0.93 . ?
C18 S1 1.785(3) . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
O1 B1 1.477(3) . ?
O2 B1 1.471(3) . ?
F1 B1 1.353(3) . ?
F2 B1 1.362(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C8 119.91(17) . . ?
O1 C1 C2 114.69(16) . . ?
C8 C1 C2 125.39(18) . . ?
C7 C2 C3 118.73(18) . . ?
C7 C2 C1 121.80(18) . . ?
C3 C2 C1 119.47(18) . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120 . . ?
C3 C4 H4 120 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C7 120.0(2) . . ?
C5 C6 H6 120 . . ?
C7 C6 H6 120 . . ?
C6 C7 C2 120.2(2) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
C1 C8 C9 120.91(18) . . ?
C1 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
O2 C9 C8 120.87(17) . . ?
O2 C9 C10 116.42(17) . . ?
C8 C9 C10 122.71(17) . . ?
C11 C10 C9 122.33(18) . . ?
C11 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
C10 C11 C12 128.36(19) . . ?
C10 C11 H11 115.8 . . ?
C12 C11 H11 115.8 . . ?
C17 C12 C13 117.65(17) . . ?
C17 C12 C11 118.86(17) . . ?
C13 C12 C11 123.49(18) . . ?
C14 C13 C12 120.79(18) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 121.16(18) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C16 C15 C14 118.59(17) . . ?
C16 C15 S1 124.35(16) . . ?
C14 C15 S1 117.05(14) . . ?
C17 C16 C15 119.71(18) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C12 122.08(17) . . ?
C16 C17 H17 119 . . ?
C12 C17 H17 119 . . ?
S1 C18 H18A 109.5 . . ?
S1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
S1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1 O1 B1 123.26(16) . . ?
C9 O2 B1 122.43(16) . . ?
C15 S1 C18 104.43(11) . . ?
F1 B1 F2 111.8(2) . . ?
F1 B1 O2 108.03(19) . . ?
F2 B1 O2 108.65(19) . . ?
F1 B1 O1 108.48(19) . . ?
F2 B1 O1 108.36(18) . . ?
O2 B1 O1 111.53(17) . . ?

# END of CIF
_chemical_melting_point          262-265\%C
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethylacetate'
