# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1482992'
_audit_update_record             
;
2016-06-01 deposited with the CCDC.
2016-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
2,2-difluoro-4-(furan-2-yl)-6-(4'-methoxy-[1,1'-biphenyl]-4-yl)-2H-1,3,2-dioxaborinin-1-ium-2-uide
_chemical_name_common            F3
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H15 B F2  O4'
_chemical_formula_weight         368.13

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.808
_cell_length_b                   13.609
_cell_length_c                   14.247
_cell_angle_alpha                76.62
_cell_angle_beta                 87.56
_cell_angle_gamma                88.26
_cell_volume                     1659.6
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4974
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      27.46

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_min  0.9640
_exptl_absorpt_correction_T_max  0.9640
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12058
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0556
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         27.52
_reflns_number_total             7508
_reflns_number_gt                6113
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_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 > 2sigma(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)+(0.0919P)²+0.2612P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7508
_refine_ls_number_parameters     487
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1535
_refine_ls_wR_factor_gt          0.1430
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
F1 F 0.42107(13) 0.76735(8) 0.32333(7) 0.0334(3) Uani 1 1 d . . .
F2 F 0.43429(12) 0.60313(8) 0.40505(7) 0.0303(2) Uani 1 1 d . . .
O7 O 0.71152(13) 0.88050(8) 0.66977(8) 0.0223(2) Uani 1 1 d . . .
O1 O -0.16523(13) 0.59442(8) 0.46342(8) 0.0235(3) Uani 1 1 d . . .
O5 O 0.31139(13) 0.64457(9) 0.25911(7) 0.0246(3) Uani 1 1 d . . .
O8 O 0.80442(13) 0.94115(9) 0.80519(8) 0.0252(3) Uani 1 1 d . . .
F3 F 0.92876(12) 0.97700(9) 0.65402(8) 0.0379(3) Uani 1 1 d . . .
F4 F 0.93244(13) 0.81580(9) 0.74486(9) 0.0423(3) Uani 1 1 d . . .
O6 O 0.20400(13) 0.69406(9) 0.40301(8) 0.0243(3) Uani 1 1 d . . .
O2 O 0.19438(15) 0.21963(9) -0.26859(8) 0.0307(3) Uani 1 1 d . . .
O3 O 0.33009(13) 0.96291(9) 0.62306(8) 0.0253(3) Uani 1 1 d . . .
O4 O 0.56030(13) 1.39101(9) 1.31243(8) 0.0246(3) Uani 1 1 d . . .
C11 C 0.18679(18) 0.53888(11) 0.17889(10) 0.0193(3) Uani 1 1 d . . .
C5 C 0.18398(18) 0.37921(11) -0.05004(10) 0.0185(3) Uani 1 1 d . . .
C28 C 0.63368(18) 1.15584(11) 1.03295(10) 0.0187(3) Uani 1 1 d . . .
C25 C 0.61784(18) 1.21525(11) 1.10833(10) 0.0185(3) Uani 1 1 d . . .
C35 C 0.56476(19) 0.99273(11) 0.74243(11) 0.0207(3) Uani 1 1 d . . .
H35A H 0.4775 1.0330 0.7421 0.025 Uiso 1 1 calc R . .
C8 C 0.18350(18) 0.43688(11) 0.02691(10) 0.0184(3) Uani 1 1 d . . .
C16 C 0.08630(18) 0.63950(11) 0.39859(10) 0.0192(3) Uani 1 1 d . . .
C10 C 0.08770(18) 0.46030(12) 0.18296(11) 0.0221(3) Uani 1 1 d . . .
H10A H 0.0213 0.4411 0.2362 0.027 Uiso 1 1 calc R . .
C31 C 0.66005(18) 1.04767(11) 0.88573(10) 0.0197(3) Uani 1 1 d . . .
C24 C 0.47968(18) 1.26297(12) 1.12517(10) 0.0201(3) Uani 1 1 d . . .
H24A H 0.3961 1.2556 1.0898 0.024 Uiso 1 1 calc R . .
C23 C 0.46455(19) 1.32084(12) 1.19336(10) 0.0214(3) Uani 1 1 d . . .
H23A H 0.3719 1.3523 1.2029 0.026 Uiso 1 1 calc R . .
C38 C 0.46793(19) 0.86474(11) 0.54341(11) 0.0222(3) Uani 1 1 d . . .
H38A H 0.5478 0.8269 0.5238 0.027 Uiso 1 1 calc R . .
C13 C 0.2799(2) 0.51794(12) 0.02220(10) 0.0244(3) Uani 1 1 d . . .
H13A H 0.3432 0.5390 -0.0323 0.029 Uiso 1 1 calc R . .
C27 C 0.72633(18) 1.28425(12) 1.23369(10) 0.0208(3) Uani 1 1 d . . .
H27A H 0.8090 1.2908 1.2702 0.025 Uiso 1 1 calc R . .
C37 C 0.46831(18) 0.91665(11) 0.61494(10) 0.0191(3) Uani 1 1 d . . .
C15 C 0.07902(18) 0.58084(11) 0.33116(10) 0.0203(3) Uani 1 1 d . . .
H15A H -0.0008 0.5370 0.3338 0.024 Uiso 1 1 calc R . .
C22 C 0.58822(18) 1.33187(11) 1.24762(10) 0.0194(3) Uani 1 1 d . . .
C36 C 0.58541(18) 0.93084(11) 0.67727(10) 0.0187(3) Uani 1 1 d . . .
C9 C 0.08677(19) 0.41025(12) 0.10868(10) 0.0219(3) Uani 1 1 d . . .
H9A H 0.0200 0.3575 0.1133 0.026 Uiso 1 1 calc R . .
C7 C 0.2815(2) 0.34938(12) -0.20390(11) 0.0244(3) Uani 1 1 d . . .
H7A H 0.3467 0.3672 -0.2579 0.029 Uiso 1 1 calc R . .
C29 C 0.52634(19) 1.16864(12) 0.96077(11) 0.0226(3) Uani 1 1 d . . .
H29A H 0.4451 1.2138 0.9613 0.027 Uiso 1 1 calc R . .
C14 C 0.19348(18) 0.58883(11) 0.25941(10) 0.0190(3) Uani 1 1 d . . .
C2 C 0.18578(19) 0.26822(12) -0.19459(10) 0.0223(3) Uani 1 1 d . . .
C6 C 0.28005(19) 0.40382(12) -0.13278(11) 0.0224(3) Uani 1 1 d . . .
H6A H 0.3445 0.4582 -0.1401 0.027 Uiso 1 1 calc R . .
C12 C 0.2836(2) 0.56764(12) 0.09678(11) 0.0233(3) Uani 1 1 d . . .
H12A H 0.3504 0.6203 0.0924 0.028 Uiso 1 1 calc R . .
C3 C 0.0892(2) 0.24216(13) -0.11398(12) 0.0303(4) Uani 1 1 d . . .
H3A H 0.0243 0.1881 -0.1072 0.036 Uiso 1 1 calc R . .
C4 C 0.0899(2) 0.29748(13) -0.04287(12) 0.0307(4) Uani 1 1 d . . .
H4A H 0.0250 0.2790 0.0112 0.037 Uiso 1 1 calc R . .
C33 C 0.75374(19) 1.08712(12) 1.02986(11) 0.0237(3) Uani 1 1 d . . .
H33A H 0.8255 1.0766 1.0774 0.028 Uiso 1 1 calc R . .
C26 C 0.73977(18) 1.22659(12) 1.16445(10) 0.0199(3) Uani 1 1 d . . .
H26A H 0.8324 1.1948 1.1553 0.024 Uiso 1 1 calc R . .
C34 C 0.67721(18) 0.99299(11) 0.80789(10) 0.0195(3) Uani 1 1 d . . .
C21 C 0.6836(2) 1.40534(13) 1.36947(11) 0.0263(4) Uani 1 1 d . . .
H21A H 0.6504 1.4479 1.4118 0.039 Uiso 1 1 calc R . .
H21B H 0.7657 1.4367 1.3279 0.039 Uiso 1 1 calc R . .
H21C H 0.7176 1.3411 1.4070 0.039 Uiso 1 1 calc R . .
C32 C 0.76848(19) 1.03413(12) 0.95758(11) 0.0237(3) Uani 1 1 d . . .
H32A H 0.8503 0.9895 0.9566 0.028 Uiso 1 1 calc R . .
C39 C 0.3207(2) 0.88039(12) 0.50518(11) 0.0256(4) Uani 1 1 d . . .
H39A H 0.2852 0.8548 0.4553 0.031 Uiso 1 1 calc R . .
C18 C -0.05577(19) 0.70416(12) 0.53416(11) 0.0236(3) Uani 1 1 d . . .
H18A H 0.0143 0.7470 0.5499 0.028 Uiso 1 1 calc R . .
C17 C -0.03687(18) 0.64816(12) 0.46591(10) 0.0204(3) Uani 1 1 d . . .
C30 C 0.53921(19) 1.11527(12) 0.88879(11) 0.0224(3) Uani 1 1 d . . .
H30A H 0.4663 1.1248 0.8420 0.027 Uiso 1 1 calc R . .
C19 C -0.2033(2) 0.68364(12) 0.57594(11) 0.0253(3) Uani 1 1 d . . .
H19A H -0.2493 0.7103 0.6248 0.030 Uiso 1 1 calc R . .
C20 C -0.2645(2) 0.61771(13) 0.53097(11) 0.0256(3) Uani 1 1 d . . .
H20A H -0.3615 0.5918 0.5445 0.031 Uiso 1 1 calc R . .
C1 C 0.0942(3) 0.13792(14) -0.26356(13) 0.0365(4) Uani 1 1 d . . .
H1A H 0.1117 0.1105 -0.3195 0.055 Uiso 1 1 calc R . .
H1B H -0.0091 0.1620 -0.2613 0.055 Uiso 1 1 calc R . .
H1C H 0.1129 0.0863 -0.2065 0.055 Uiso 1 1 calc R . .
C40 C 0.2425(2) 0.93931(14) 0.55505(12) 0.0277(4) Uani 1 1 d . . .
H40A H 0.1422 0.9610 0.5446 0.033 Uiso 1 1 calc R . .
B1 B 0.3480(2) 0.67832(14) 0.34799(12) 0.0227(4) Uani 1 1 d . . .
B2 B 0.8487(2) 0.90288(14) 0.71794(14) 0.0254(4) Uani 1 1 d . . .


_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
F1 B1 1.355(2) . ?
F2 B1 1.381(2) . ?
O7 C36 1.3008(19) . ?
O7 B2 1.488(2) . ?
O1 C20 1.3579(18) . ?
O1 C17 1.3712(18) . ?
O5 C14 1.3038(18) . ?
O5 B1 1.4938(17) . ?
O8 C34 1.310(2) . ?
O8 B2 1.4881(19) . ?
F3 B2 1.381(2) . ?
F4 B2 1.362(2) . ?
O6 C16 1.3053(18) . ?
O6 B1 1.499(2) . ?
O2 C2 1.3665(16) . ?
O2 C1 1.427(2) . ?
O3 C40 1.3640(18) . ?
O3 C37 1.3664(19) . ?
O4 C22 1.3686(16) . ?
O4 C21 1.4279(18) . ?
C11 C10 1.390(2) . ?
C11 C12 1.404(2) . ?
C11 C14 1.4665(17) . ?
C5 C4 1.390(2) . ?
C5 C6 1.403(2) . ?
C5 C8 1.4884(17) . ?
C28 C33 1.396(2) . ?
C28 C29 1.404(2) . ?
C28 C25 1.4862(18) . ?
C25 C26 1.399(2) . ?
C25 C24 1.400(2) . ?
C35 C34 1.390(2) . ?
C35 C36 1.3938(18) . ?
C8 C9 1.398(2) . ?
C8 C13 1.400(2) . ?
C16 C15 1.3884(18) . ?
C16 C17 1.438(2) . ?
C10 C9 1.3851(18) . ?
C31 C30 1.391(2) . ?
C31 C32 1.407(2) . ?
C31 C34 1.4721(18) . ?
C24 C23 1.3850(19) . ?
C23 C22 1.394(2) . ?
C38 C37 1.3679(18) . ?
C38 C39 1.419(2) . ?
C13 C12 1.3872(19) . ?
C27 C22 1.389(2) . ?
C27 C26 1.3948(19) . ?
C37 C36 1.435(2) . ?
C15 C14 1.393(2) . ?
C7 C6 1.3861(19) . ?
C7 C2 1.389(2) . ?
C29 C30 1.3863(19) . ?
C2 C3 1.384(2) . ?
C3 C4 1.395(2) . ?
C33 C32 1.387(2) . ?
C39 C40 1.346(2) . ?
C18 C17 1.3694(18) . ?
C18 C19 1.414(2) . ?
C19 C20 1.353(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
C36 O7 B2 119.60(11) . . ?
C20 O1 C17 106.23(11) . . ?
C14 O5 B1 120.12(12) . . ?
C34 O8 B2 119.98(12) . . ?
C16 O6 B1 119.37(11) . . ?
C2 O2 C1 117.75(13) . . ?
C40 O3 C37 106.17(12) . . ?
C22 O4 C21 117.17(12) . . ?
C10 C11 C12 118.39(13) . . ?
C10 C11 C14 120.97(13) . . ?
C12 C11 C14 120.61(14) . . ?
C4 C5 C6 116.66(12) . . ?
C4 C5 C8 121.46(13) . . ?
C6 C5 C8 121.88(13) . . ?
C33 C28 C29 117.62(13) . . ?
C33 C28 C25 122.43(13) . . ?
C29 C28 C25 119.95(14) . . ?
C26 C25 C24 117.40(13) . . ?
C26 C25 C28 121.67(14) . . ?
C24 C25 C28 120.93(13) . . ?
C34 C35 C36 118.64(15) . . ?
C9 C8 C13 117.12(12) . . ?
C9 C8 C5 120.51(13) . . ?
C13 C8 C5 122.37(13) . . ?
O6 C16 C15 122.19(14) . . ?
O6 C16 C17 114.95(12) . . ?
C15 C16 C17 122.81(14) . . ?
C9 C10 C11 120.75(14) . . ?
C30 C31 C32 118.61(13) . . ?
C30 C31 C34 121.12(13) . . ?
C32 C31 C34 120.25(14) . . ?
C23 C24 C25 121.50(13) . . ?
C24 C23 C22 119.99(14) . . ?
C37 C38 C39 105.90(14) . . ?
C12 C13 C8 121.65(14) . . ?
C22 C27 C26 119.32(13) . . ?
C38 C37 O3 110.26(13) . . ?
C38 C37 C36 131.57(15) . . ?
O3 C37 C36 118.16(12) . . ?
C16 C15 C14 118.81(14) . . ?
O4 C22 C27 125.16(13) . . ?
O4 C22 C23 114.90(14) . . ?
C27 C22 C23 119.94(13) . . ?
O7 C36 C35 122.32(14) . . ?
O7 C36 C37 115.22(12) . . ?
C35 C36 C37 122.45(14) . . ?
C10 C9 C8 121.74(14) . . ?
C6 C7 C2 120.05(14) . . ?
C30 C29 C28 121.26(15) . . ?
O5 C14 C15 121.01(12) . . ?
O5 C14 C11 116.27(13) . . ?
C15 C14 C11 122.69(14) . . ?
O2 C2 C3 124.53(14) . . ?
O2 C2 C7 115.88(14) . . ?
C3 C2 C7 119.58(13) . . ?
C7 C6 C5 121.82(14) . . ?
C13 C12 C11 120.32(14) . . ?
C2 C3 C4 119.57(15) . . ?
C5 C4 C3 122.31(15) . . ?
C32 C33 C28 121.56(14) . . ?
C27 C26 C25 121.83(15) . . ?
O8 C34 C35 121.12(13) . . ?
O8 C34 C31 115.93(13) . . ?
C35 C34 C31 122.92(14) . . ?
C33 C32 C31 120.21(15) . . ?
C40 C39 C38 106.83(13) . . ?
C17 C18 C19 106.13(14) . . ?
C18 C17 O1 110.04(13) . . ?
C18 C17 C16 132.16(15) . . ?
O1 C17 C16 117.77(12) . . ?
C29 C30 C31 120.73(14) . . ?
C20 C19 C18 106.68(13) . . ?
C19 C20 O1 110.92(15) . . ?
C39 C40 O3 110.84(16) . . ?
F1 B1 F2 112.18(14) . . ?
F1 B1 O5 109.85(13) . . ?
F2 B1 O5 108.19(13) . . ?
F1 B1 O6 108.13(13) . . ?
F2 B1 O6 108.76(13) . . ?
O5 B1 O6 109.71(13) . . ?
F4 B2 F3 112.01(16) . . ?
F4 B2 O8 109.13(14) . . ?
F3 B2 O8 108.43(13) . . ?
F4 B2 O7 108.31(13) . . ?
F3 B2 O7 108.38(14) . . ?
O8 B2 O7 110.59(13) . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.075
_exptl_crystal_recrystallization_method 'solvent diffusion'
_chemical_properties_physical    Heat-sensitive
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1486089'
_audit_update_record             
;
2016-06-16 deposited with the CCDC.
2016-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
2,2-difluoro-4-(furan-2-yl)-6-(4-(naphthalen-2-yl)phenyl)-2H-1,3,2-dioxaborinin-1-ium-2-uide
_chemical_name_common            F2
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H15 B F2 O3'
_chemical_formula_weight         388.16

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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                   16.880
_cell_length_b                   9.056
_cell_length_c                   11.782
_cell_angle_alpha                90.00
_cell_angle_beta                 97.50
_cell_angle_gamma                90.00
_cell_volume                     1785.6
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1409
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      23.35

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_min  0.9663
_exptl_absorpt_correction_T_max  0.9663
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8561
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_sigmaI/netI    0.0479
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3136
_reflns_number_gt                2022
_reflns_threshold_expression     >2sigma(I)

__computing_data_collection      'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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 > 2sigma(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)+(0.0809P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3136
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1469
_refine_ls_wR_factor_gt          0.1301
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O6 O 0.37967(10) 0.31620(18) 0.33440(14) 0.0368(5) Uani 1 1 d . . .
O1 O 0.40561(10) 0.67260(17) 0.45783(15) 0.0398(5) Uani 1 1 d . . .
O5 O 0.25237(9) 0.21073(17) 0.37116(14) 0.0367(4) Uani 1 1 d . . .
F1 F 0.37186(9) 0.08596(15) 0.42097(14) 0.0537(5) Uani 1 1 d . . .
C7 C -0.07953(15) 0.4096(3) 0.69777(19) 0.0326(6) Uani 1 1 d . . .
H5A H -0.0474 0.4926 0.7127 0.039 Uiso 1 1 calc R . .
F2 F 0.32409(9) 0.11367(17) 0.23340(14) 0.0560(5) Uani 1 1 d . . .
C18 C 0.29728(14) 0.4356(3) 0.45303(19) 0.0314(6) Uani 1 1 d . . .
H7A H 0.2905 0.5129 0.5028 0.038 Uiso 1 1 calc R . .
C17 C 0.24095(14) 0.3257(2) 0.43478(19) 0.0298(6) Uani 1 1 d . . .
C6 C -0.19885(14) 0.2701(2) 0.7276(2) 0.0311(6) Uani 1 1 d . . .
C14 C 0.16410(14) 0.3280(2) 0.4805(2) 0.0298(6) Uani 1 1 d . . .
C12 C 0.08043(14) 0.4102(2) 0.6187(2) 0.0317(6) Uani 1 1 d . . .
H11A H 0.0735 0.4697 0.6810 0.038 Uiso 1 1 calc R . .
C8 C -0.05676(14) 0.3030(3) 0.6266(2) 0.0314(6) Uani 1 1 d . . .
C11 C 0.01825(14) 0.3168(2) 0.5732(2) 0.0300(6) Uani 1 1 d . . .
C1 C -0.27050(15) 0.2571(3) 0.7799(2) 0.0402(7) Uani 1 1 d . . .
H14A H -0.3023 0.1734 0.7668 0.048 Uiso 1 1 calc R . .
C19 C 0.36440(14) 0.4304(2) 0.3965(2) 0.0305(6) Uani 1 1 d . . .
C5 C -0.15109(15) 0.3976(2) 0.7500(2) 0.0315(6) Uani 1 1 d . . .
C13 C 0.15179(14) 0.4162(2) 0.5734(2) 0.0315(6) Uani 1 1 d . . .
H17A H 0.1920 0.4798 0.6052 0.038 Uiso 1 1 calc R . .
C21 C 0.48719(15) 0.5691(3) 0.3453(2) 0.0370(6) Uani 1 1 d . . .
H18A H 0.5096 0.5019 0.2989 0.044 Uiso 1 1 calc R . .
C4 C -0.17573(16) 0.5099(3) 0.8200(2) 0.0397(7) Uani 1 1 d . . .
H19A H -0.1449 0.5947 0.8340 0.048 Uiso 1 1 calc R . .
C20 C 0.42002(14) 0.5490(3) 0.3962(2) 0.0315(6) Uani 1 1 d . . .
C16 C 0.02984(14) 0.2339(3) 0.4765(2) 0.0348(6) Uani 1 1 d . . .
H21A H -0.0115 0.1750 0.4417 0.042 Uiso 1 1 calc R . .
C9 C -0.10667(16) 0.1770(3) 0.6046(2) 0.0399(7) Uani 1 1 d . . .
H22A H -0.0925 0.1040 0.5555 0.048 Uiso 1 1 calc R . .
C10 C -0.17512(16) 0.1609(3) 0.6539(2) 0.0415(7) Uani 1 1 d . . .
H23A H -0.2064 0.0769 0.6386 0.050 Uiso 1 1 calc R . .
C2 C -0.29218(16) 0.3666(3) 0.8486(2) 0.0417(7) Uani 1 1 d . . .
H24A H -0.3384 0.3566 0.8831 0.050 Uiso 1 1 calc R . .
C15 C 0.10132(15) 0.2376(3) 0.4317(2) 0.0345(6) Uani 1 1 d . . .
H25A H 0.1079 0.1796 0.3685 0.041 Uiso 1 1 calc R . .
C3 C -0.24549(15) 0.4944(3) 0.8678(2) 0.0444(7) Uani 1 1 d . . .
H26A H -0.2618 0.5695 0.9134 0.053 Uiso 1 1 calc R . .
C23 C 0.51630(16) 0.7115(3) 0.3765(2) 0.0416(7) Uani 1 1 d . . .
H27A H 0.5616 0.7564 0.3551 0.050 Uiso 1 1 calc R . .
C22 C 0.46539(16) 0.7692(3) 0.4433(2) 0.0464(7) Uani 1 1 d . . .
H28A H 0.4703 0.8631 0.4754 0.056 Uiso 1 1 calc R . .
B1 B 0.33268(18) 0.1781(3) 0.3391(3) 0.0388(7) Uani 1 1 d . . .


_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
O6 C19 1.312(3) . ?
O6 B1 1.485(3) . ?
O1 C22 1.363(3) . ?
O1 C20 1.373(3) . ?
O5 C17 1.312(3) . ?
O5 B1 1.484(3) . ?
F1 B1 1.378(3) . ?
C7 C8 1.367(3) . ?
C7 C5 1.429(3) . ?
C7 H5A 0.9300 . ?
F2 B1 1.366(3) . ?
C18 C17 1.374(3) . ?
C18 C19 1.388(3) . ?
C18 H7A 0.9300 . ?
C17 C14 1.468(3) . ?
C6 C10 1.408(3) . ?
C6 C5 1.413(3) . ?
C6 C1 1.432(3) . ?
C14 C13 1.392(3) . ?
C14 C15 1.402(3) . ?
C12 C13 1.381(3) . ?
C12 C11 1.399(3) . ?
C12 H11A 0.9300 . ?
C8 C9 1.422(3) . ?
C8 C11 1.491(3) . ?
C11 C16 1.400(3) . ?
C1 C2 1.360(3) . ?
C1 H14A 0.9300 . ?
C19 C20 1.427(3) . ?
C5 C4 1.406(3) . ?
C13 H17A 0.9300 . ?
C21 C20 1.362(3) . ?
C21 C23 1.412(3) . ?
C21 H18A 0.9300 . ?
C4 C3 1.377(3) . ?
C4 H19A 0.9300 . ?
C16 C15 1.379(3) . ?
C16 H21A 0.9300 . ?
C9 C10 1.367(3) . ?
C9 H22A 0.9300 . ?
C10 H23A 0.9300 . ?
C2 C3 1.402(4) . ?
C2 H24A 0.9300 . ?
C15 H25A 0.9300 . ?
C3 H26A 0.9300 . ?
C23 C22 1.344(3) . ?
C23 H27A 0.9300 . ?
C22 H28A 0.9300 . ?

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
C19 O6 B1 119.87(19) . . ?
C22 O1 C20 105.75(19) . . ?
C17 O5 B1 120.70(19) . . ?
C8 C7 C5 122.1(2) . . ?
C8 C7 H5A 118.9 . . ?
C5 C7 H5A 118.9 . . ?
C17 C18 C19 119.5(2) . . ?
C17 C18 H7A 120.3 . . ?
C19 C18 H7A 120.3 . . ?
O5 C17 C18 120.9(2) . . ?
O5 C17 C14 115.1(2) . . ?
C18 C17 C14 124.0(2) . . ?
C10 C6 C5 119.2(2) . . ?
C10 C6 C1 122.1(2) . . ?
C5 C6 C1 118.7(2) . . ?
C13 C14 C15 118.4(2) . . ?
C13 C14 C17 121.8(2) . . ?
C15 C14 C17 119.9(2) . . ?
C13 C12 C11 121.6(2) . . ?
C13 C12 H11A 119.2 . . ?
C11 C12 H11A 119.2 . . ?
C7 C8 C9 118.1(2) . . ?
C7 C8 C11 121.5(2) . . ?
C9 C8 C11 120.4(2) . . ?
C12 C11 C16 117.3(2) . . ?
C12 C11 C8 121.7(2) . . ?
C16 C11 C8 121.0(2) . . ?
C2 C1 C6 120.3(2) . . ?
C2 C1 H14A 119.9 . . ?
C6 C1 H14A 119.9 . . ?
O6 C19 C18 121.8(2) . . ?
O6 C19 C20 114.5(2) . . ?
C18 C19 C20 123.6(2) . . ?
C4 C5 C6 119.7(2) . . ?
C4 C5 C7 121.9(2) . . ?
C6 C5 C7 118.4(2) . . ?
C12 C13 C14 120.5(2) . . ?
C12 C13 H17A 119.7 . . ?
C14 C13 H17A 119.7 . . ?
C20 C21 C23 106.8(2) . . ?
C20 C21 H18A 126.6 . . ?
C23 C21 H18A 126.6 . . ?
C3 C4 C5 120.0(2) . . ?
C3 C4 H19A 120.0 . . ?
C5 C4 H19A 120.0 . . ?
C21 C20 O1 109.8(2) . . ?
C21 C20 C19 133.4(2) . . ?
O1 C20 C19 116.8(2) . . ?
C15 C16 C11 121.3(2) . . ?
C15 C16 H21A 119.3 . . ?
C11 C16 H21A 119.3 . . ?
C10 C9 C8 121.4(2) . . ?
C10 C9 H22A 119.3 . . ?
C8 C9 H22A 119.3 . . ?
C9 C10 C6 120.7(2) . . ?
C9 C10 H23A 119.6 . . ?
C6 C10 H23A 119.6 . . ?
C1 C2 C3 120.6(2) . . ?
C1 C2 H24A 119.7 . . ?
C3 C2 H24A 119.7 . . ?
C16 C15 C14 120.7(2) . . ?
C16 C15 H25A 119.7 . . ?
C14 C15 H25A 119.7 . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H26A 119.7 . . ?
C2 C3 H26A 119.7 . . ?
C22 C23 C21 106.3(2) . . ?
C22 C23 H27A 126.9 . . ?
C21 C23 H27A 126.9 . . ?
C23 C22 O1 111.4(2) . . ?
C23 C22 H28A 124.3 . . ?
O1 C22 H28A 124.3 . . ?
F2 B1 F1 111.3(2) . . ?
F2 B1 O5 109.0(2) . . ?
F1 B1 O5 108.3(2) . . ?
F2 B1 O6 108.6(2) . . ?
F1 B1 O6 109.0(2) . . ?
O5 B1 O6 110.6(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.055
_exptl_crystal_recrystallization_method 'Solvent diffusion'
_chemical_properties_physical    ', Light-sensitive,Photo-sensitive'
_exptl_crystal_preparation       ', Luminescent'
