# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2161374'
loop_
_audit_author_name
_audit_author_address
'Samuel Guieu'
;University of Aveiro
Portugal
;
_audit_update_record             
;
2022-03-23 deposited with the CCDC.	2023-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
(1E,4Z,6E)-5-hydroxy-1,7-bis(4-methoxyphenyl)hepta-1,4,6-trien-3-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H20 O4'
_chemical_formula_sum            'C21 H20 O4'
_chemical_formula_weight         336.37

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   11.6910(19)
_cell_length_b                   10.8177(18)
_cell_length_c                   13.581(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.087(5)
_cell_angle_gamma                90
_cell_volume                     1696.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5722
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      28.30

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   0.6585
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19468
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.580
_diffrn_reflns_theta_max         28.439
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2127
_reflns_number_gt                1602
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0715P)²+0.9850P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2127
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1483
_refine_ls_wR_factor_gt          0.1311
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O01 O 0.89136(10) 0.69879(9) 0.34565(7) 0.0374(3) Uani 1 1 d . . . . .
O02 O 0.55526(9) 0.31554(10) -0.16291(8) 0.0363(3) Uani 1 1 d . . . . .
C11 C 0.95246(13) 0.63140(14) 0.42805(10) 0.0346(3) Uani 1 1 d . . . . .
H11A H 0.902212 0.566504 0.447868 0.052 Uiso 1 1 calc R U . . .
H11C H 0.975302 0.687757 0.484213 0.052 Uiso 1 1 calc R U . . .
H11B H 1.021782 0.593733 0.408586 0.052 Uiso 1 1 calc R U . . .
C08 C 0.84283(11) 0.63323(13) 0.26366(10) 0.0278(3) Uani 1 1 d . . . . .
C09 C 0.77862(13) 0.70242(13) 0.18731(11) 0.0325(3) Uani 1 1 d . . . . .
H09 H 0.773129 0.789536 0.194086 0.039 Uiso 1 1 calc R U . . .
C10 C 0.72336(13) 0.64545(13) 0.10251(10) 0.0313(3) Uani 1 1 d . . . . .
H10 H 0.678629 0.693736 0.052068 0.038 Uiso 1 1 calc R U . . .
C05 C 0.73174(11) 0.51704(12) 0.08894(10) 0.0265(3) Uani 1 1 d . . . . .
C04 C 0.67376(11) 0.45247(13) 0.00062(10) 0.0286(3) Uani 1 1 d . . . . .
H04 H 0.681741 0.365100 -0.000285 0.034 Uiso 1 1 calc R U . . .
C03 C 0.61031(12) 0.50485(14) -0.07933(10) 0.0310(3) Uani 1 1 d . . . . .
H03 H 0.601430 0.592156 -0.079802 0.037 Uiso 1 1 calc R U . . .
C02 C 0.55409(11) 0.43538(14) -0.16569(9) 0.0290(3) Uani 1 1 d . . . . .
C01 C 0.500000 0.49907(18) -0.250000 0.0299(4) Uani 1 2 d S T P . .
H01 H 0.499997 0.586893 -0.249999 0.036 Uiso 1 2 calc R U P . .
C06 C 0.79822(11) 0.45025(12) 0.16479(10) 0.0284(3) Uani 1 1 d . . . . .
H06 H 0.806406 0.363590 0.156975 0.034 Uiso 1 1 calc R U . . .
C07 C 0.85314(11) 0.50642(13) 0.25183(10) 0.0289(3) Uani 1 1 d . . . . .
H07 H 0.897337 0.458346 0.302737 0.035 Uiso 1 1 calc R U . . .
H02 H 0.506(4) 0.290(3) -0.228(3) 0.043 Uiso 0.5 1 d . U P . .


_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
O01 C08 1.3657(16) . ?
O01 C11 1.4288(16) . ?
O02 C02 1.2970(18) . ?
O02 H02 1.01(4) . ?
C11 H11A 0.9800 . ?
C11 H11C 0.9800 . ?
C11 H11B 0.9800 . ?
C08 C07 1.3887(19) . ?
C08 C09 1.3975(18) . ?
C09 C10 1.3742(19) . ?
C09 H09 0.9500 . ?
C10 C05 1.4068(19) . ?
C10 H10 0.9500 . ?
C05 C06 1.3908(17) . ?
C05 C04 1.4592(18) . ?
C04 C03 1.3402(18) . ?
C04 H04 0.9500 . ?
C03 C02 1.4591(18) . ?
C03 H03 0.9500 . ?
C02 C01 1.3989(16) . ?
C01 H01 0.9500 . ?
C06 C07 1.3926(18) . ?
C06 H06 0.9500 . ?
C07 H07 0.9500 . ?

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
C08 O01 C11 117.75(11) . . ?
C02 O02 H02 104.2(17) . . ?
O01 C11 H11A 109.5 . . ?
O01 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
O01 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11C C11 H11B 109.5 . . ?
O01 C08 C07 125.08(12) . . ?
O01 C08 C09 115.60(12) . . ?
C07 C08 C09 119.31(12) . . ?
C10 C09 C08 120.53(13) . . ?
C10 C09 H09 119.7 . . ?
C08 C09 H09 119.7 . . ?
C09 C10 C05 121.29(12) . . ?
C09 C10 H10 119.4 . . ?
C05 C10 H10 119.4 . . ?
C06 C05 C10 117.28(12) . . ?
C06 C05 C04 119.53(12) . . ?
C10 C05 C04 123.19(12) . . ?
C03 C04 C05 126.12(13) . . ?
C03 C04 H04 116.9 . . ?
C05 C04 H04 116.9 . . ?
C04 C03 C02 123.71(14) . . ?
C04 C03 H03 118.1 . . ?
C02 C03 H03 118.1 . . ?
O02 C02 C01 121.16(13) . . ?
O02 C02 C03 119.35(12) . . ?
C01 C02 C03 119.49(14) . . ?
C02 C01 C02 120.99(18) . 2_654 ?
C02 C01 H01 119.5 . . ?
C02 C01 H01 119.5 2_654 . ?
C05 C06 C07 122.07(12) . . ?
C05 C06 H06 119.0 . . ?
C07 C06 H06 119.0 . . ?
C08 C07 C06 119.50(12) . . ?
C08 C07 H07 120.3 . . ?
C06 C07 H07 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 O01 C08 C07 -3.5(2) . . . . ?
C11 O01 C08 C09 176.60(12) . . . . ?
O01 C08 C09 C10 -178.22(12) . . . . ?
C07 C08 C09 C10 1.9(2) . . . . ?
C08 C09 C10 C05 -1.5(2) . . . . ?
C09 C10 C05 C06 0.0(2) . . . . ?
C09 C10 C05 C04 179.42(12) . . . . ?
C06 C05 C04 C03 -177.72(13) . . . . ?
C10 C05 C04 C03 2.9(2) . . . . ?
C05 C04 C03 C02 -179.93(12) . . . . ?
C04 C03 C02 O02 6.7(2) . . . . ?
C04 C03 C02 C01 -173.24(11) . . . . ?
O02 C02 C01 C02 -0.34(9) . . . 2_654 ?
C03 C02 C01 C02 179.60(13) . . . 2_654 ?
C10 C05 C06 C07 1.09(19) . . . . ?
C04 C05 C06 C07 -178.37(11) . . . . ?
O01 C08 C07 C06 179.29(12) . . . . ?
C09 C08 C07 C06 -0.8(2) . . . . ?
C05 C06 C07 C08 -0.7(2) . . . . ?

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.048


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: tetrahydrofuran'
_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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2161375'
loop_
_audit_author_name
_audit_author_address
'Samuel Guieu'
;University of Aveiro
Portugal
;
_audit_update_record             
;
2022-03-23 deposited with the CCDC.	2023-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
2,2-difluoro-4,6-bis((E)-4-methoxystyryl)-2H-1l3,3,2l4-dioxaborinine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H23 B F2 O4.50'
_chemical_formula_weight         420.22

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.84(2)
_cell_length_b                   10.70(3)
_cell_length_c                   11.53(3)
_cell_angle_alpha                66.33(5)
_cell_angle_beta                 75.73(7)
_cell_angle_gamma                85.18(5)
_cell_volume                     968(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2723
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      27.43

_exptl_crystal_description       flake
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   0.5588
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11794
_diffrn_reflns_av_unetI/netI     0.0694
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.079
_diffrn_reflns_theta_max         28.792
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4937
_reflns_number_gt                3272
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0566P)²+0.2084P] 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         4937
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1442
_refine_ls_wR_factor_gt          0.1264
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.29074(13) 0.63167(11) 0.32627(11) 0.0343(3) Uani 1 1 d . . . . .
F2 F 0.40825(13) 0.82068(11) 0.16698(10) 0.0341(3) Uani 1 1 d . . . . .
O04 O 1.29900(16) 0.15252(14) 0.21594(13) 0.0354(3) Uani 1 1 d . . . . .
O01 O 0.06781(15) 1.16331(14) 0.89815(12) 0.0305(3) Uani 1 1 d . . . . .
O03 O 0.55698(15) 0.65695(14) 0.28337(13) 0.0307(3) Uani 1 1 d . . . . .
O02 O 0.37979(15) 0.79209(14) 0.37969(12) 0.0301(3) Uani 1 1 d . . . . .
C21 C 1.3391(3) 0.1269(2) 0.1007(2) 0.0392(5) Uani 1 1 d . . . . .
H21A H 1.251848 0.079714 0.095954 0.059 Uiso 1 1 calc R U . . .
H21C H 1.431655 0.069581 0.101752 0.059 Uiso 1 1 calc R U . . .
H21B H 1.361432 0.213586 0.024648 0.059 Uiso 1 1 calc R U . . .
C18 C 1.1773(2) 0.23437(18) 0.22708(18) 0.0253(4) Uani 1 1 d . . . . .
C17 C 1.1467(2) 0.26518(19) 0.33522(18) 0.0285(4) Uani 1 1 d . . . . .
H17 H 1.209071 0.227300 0.397195 0.034 Uiso 1 1 calc R U . . .
C16 C 1.0288(2) 0.34891(19) 0.35436(17) 0.0269(4) Uani 1 1 d . . . . .
H16 H 1.009437 0.369755 0.429383 0.032 Uiso 1 1 calc R U . . .
C15 C 0.9355(2) 0.40476(18) 0.26550(17) 0.0231(4) Uani 1 1 d . . . . .
C14 C 0.8090(2) 0.49369(18) 0.27915(17) 0.0255(4) Uani 1 1 d . . . . .
H14 H 0.751900 0.523214 0.213152 0.031 Uiso 1 1 calc R U . . .
C13 C 0.7614(2) 0.53998(18) 0.37239(17) 0.0249(4) Uani 1 1 d . . . . .
H13 H 0.817712 0.516176 0.438462 0.030 Uiso 1 1 calc R U . . .
C12 C 0.6284(2) 0.62450(18) 0.37700(17) 0.0242(4) Uani 1 1 d . . . . .
C11 C 0.5780(2) 0.67126(18) 0.47376(17) 0.0248(4) Uani 1 1 d . . . . .
H11 H 0.627693 0.642333 0.544360 0.030 Uiso 1 1 calc R U . . .
C10 C 0.4563(2) 0.75958(18) 0.46986(17) 0.0235(4) Uani 1 1 d . . . . .
C09 C 0.4103(2) 0.82040(18) 0.56189(17) 0.0241(4) Uani 1 1 d . . . . .
H09 H 0.470055 0.803120 0.624742 0.029 Uiso 1 1 calc R U . . .
C08 C 0.2877(2) 0.90028(18) 0.56391(17) 0.0242(4) Uani 1 1 d . . . . .
H08 H 0.230014 0.914107 0.500386 0.029 Uiso 1 1 calc R U . . .
C05 C 0.2319(2) 0.96811(17) 0.65039(16) 0.0221(4) Uani 1 1 d . . . . .
C06 C 0.0907(2) 1.03262(19) 0.64937(17) 0.0256(4) Uani 1 1 d . . . . .
H06 H 0.032763 1.030869 0.590730 0.031 Uiso 1 1 calc R U . . .
C07 C 0.0306(2) 1.09929(19) 0.72972(17) 0.0254(4) Uani 1 1 d . . . . .
H07 H -0.067236 1.143052 0.726867 0.030 Uiso 1 1 calc R U . . .
C02 C 0.1142(2) 1.10177(18) 0.81441(16) 0.0234(4) Uani 1 1 d . . . . .
C01 C -0.0775(2) 1.2300(2) 0.8969(2) 0.0347(5) Uani 1 1 d . . . . .
H01A H -0.073012 1.302759 0.810654 0.052 Uiso 1 1 calc R U . . .
H01C H -0.099781 1.269528 0.962627 0.052 Uiso 1 1 calc R U . . .
H01B H -0.160079 1.164005 0.916639 0.052 Uiso 1 1 calc R U . . .
C19 C 1.0857(2) 0.28671(19) 0.13828(18) 0.0271(4) Uani 1 1 d . . . . .
H19 H 1.105180 0.265219 0.063619 0.033 Uiso 1 1 calc R U . . .
C20 C 0.9664(2) 0.37018(18) 0.15955(17) 0.0260(4) Uani 1 1 d . . . . .
H20 H 0.902228 0.405676 0.098793 0.031 Uiso 1 1 calc R U . . .
C03 C 0.2569(2) 1.03883(19) 0.81659(17) 0.0260(4) Uani 1 1 d . . . . .
H03 H 0.315122 1.041475 0.874733 0.031 Uiso 1 1 calc R U . . .
C04 C 0.3144(2) 0.97336(18) 0.73641(17) 0.0252(4) Uani 1 1 d . . . . .
H04 H 0.412752 0.930376 0.739020 0.030 Uiso 1 1 calc R U . . .
B1 B 0.4071(3) 0.7252(2) 0.2879(2) 0.0282(5) Uani 1 1 d . . . . .
C22 C 0.4971(3) 0.4727(3) 0.1107(3) 0.0668(8) Uani 1 1 d . . . . .
H22A H 0.494906 0.506846 0.179180 0.080 Uiso 1 1 calc R U . . .
H22B H 0.459196 0.376707 0.155931 0.080 Uiso 1 1 calc R U . . .
C23 C 0.6163(3) 0.4511(3) -0.0394(3) 0.0575(7) Uani 1 1 d . . . . .
H23B H 0.589383 0.353207 -0.007818 0.069 Uiso 1 1 calc R U . . .
H23A H 0.718571 0.466765 -0.102608 0.069 Uiso 1 1 calc R U . . .
O05 O 0.6357(4) 0.4709(4) 0.0549(3) 0.0464(8) Uani 0.5 1 d . . P . .


_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 1.360(4) . ?
F2 B1 1.356(4) . ?
O04 C18 1.344(3) . ?
O04 C21 1.418(4) . ?
O01 C02 1.343(3) . ?
O01 C01 1.416(4) . ?
O03 C12 1.297(3) . ?
O03 B1 1.458(4) . ?
O02 C10 1.294(3) . ?
O02 B1 1.464(3) . ?
C21 H21A 0.9800 . ?
C21 H21C 0.9800 . ?
C21 H21B 0.9800 . ?
C18 C17 1.373(4) . ?
C18 C19 1.374(3) . ?
C17 C16 1.352(3) . ?
C17 H17 0.9500 . ?
C16 C15 1.388(3) . ?
C16 H16 0.9500 . ?
C15 C20 1.373(4) . ?
C15 C14 1.427(3) . ?
C14 C13 1.322(3) . ?
C14 H14 0.9500 . ?
C13 C12 1.426(3) . ?
C13 H13 0.9500 . ?
C12 C11 1.363(3) . ?
C11 C10 1.368(3) . ?
C11 H11 0.9500 . ?
C10 C09 1.418(3) . ?
C09 C08 1.325(3) . ?
C09 H09 0.9500 . ?
C08 C05 1.429(3) . ?
C08 H08 0.9500 . ?
C05 C06 1.375(4) . ?
C05 C04 1.389(3) . ?
C06 C07 1.369(3) . ?
C06 H06 0.9500 . ?
C07 C02 1.371(3) . ?
C07 H07 0.9500 . ?
C02 C03 1.380(4) . ?
C01 H01A 0.9800 . ?
C01 H01C 0.9800 . ?
C01 H01B 0.9800 . ?
C19 C20 1.364(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C03 C04 1.354(3) . ?
C03 H03 0.9500 . ?
C04 H04 0.9500 . ?
C22 O05 1.238(5) . ?
C22 C23 1.441(4) 2_665 ?
C22 C23 1.881(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 O05 1.240(5) . ?
C23 H23B 0.9900 . ?
C23 H23A 0.9900 . ?

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
C18 O04 C21 116.80(16) . . ?
C02 O01 C01 116.77(16) . . ?
C12 O03 B1 121.61(18) . . ?
C10 O02 B1 121.87(19) . . ?
O04 C21 H21A 109.5 . . ?
O04 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
O04 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21C C21 H21B 109.5 . . ?
O04 C18 C17 115.91(17) . . ?
O04 C18 C19 124.1(2) . . ?
C17 C18 C19 120.0(2) . . ?
C16 C17 C18 120.63(17) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C16 C15 120.7(2) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C20 C15 C16 117.6(2) . . ?
C20 C15 C14 118.51(17) . . ?
C16 C15 C14 123.9(2) . . ?
C13 C14 C15 127.93(18) . . ?
C13 C14 H14 116.0 . . ?
C15 C14 H14 116.0 . . ?
C14 C13 C12 122.13(18) . . ?
C14 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
O03 C12 C11 120.8(2) . . ?
O03 C12 C13 116.91(19) . . ?
C11 C12 C13 122.31(18) . . ?
C12 C11 C10 120.43(18) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
O02 C10 C11 120.57(19) . . ?
O02 C10 C09 117.5(2) . . ?
C11 C10 C09 121.96(18) . . ?
C08 C09 C10 122.78(18) . . ?
C08 C09 H09 118.6 . . ?
C10 C09 H09 118.6 . . ?
C09 C08 C05 127.66(18) . . ?
C09 C08 H08 116.2 . . ?
C05 C08 H08 116.2 . . ?
C06 C05 C04 117.5(2) . . ?
C06 C05 C08 119.52(18) . . ?
C04 C05 C08 123.0(2) . . ?
C07 C06 C05 122.43(18) . . ?
C07 C06 H06 118.8 . . ?
C05 C06 H06 118.8 . . ?
C06 C07 C02 118.8(2) . . ?
C06 C07 H07 120.6 . . ?
C02 C07 H07 120.6 . . ?
O01 C02 C07 124.5(2) . . ?
O01 C02 C03 115.59(17) . . ?
C07 C02 C03 119.9(2) . . ?
O01 C01 H01A 109.5 . . ?
O01 C01 H01C 109.5 . . ?
H01A C01 H01C 109.5 . . ?
O01 C01 H01B 109.5 . . ?
H01A C01 H01B 109.5 . . ?
H01C C01 H01B 109.5 . . ?
C20 C19 C18 118.6(2) . . ?
C20 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
C19 C20 C15 122.44(17) . . ?
C19 C20 H20 118.8 . . ?
C15 C20 H20 118.8 . . ?
C04 C03 C02 120.41(18) . . ?
C04 C03 H03 119.8 . . ?
C02 C03 H03 119.8 . . ?
C03 C04 C05 121.0(2) . . ?
C03 C04 H04 119.5 . . ?
C05 C04 H04 119.5 . . ?
F2 B1 F1 110.36(19) . . ?
F2 B1 O03 108.13(19) . . ?
F1 B1 O03 109.3(2) . . ?
F2 B1 O02 109.0(3) . . ?
F1 B1 O02 108.6(2) . . ?
O03 B1 O02 111.46(16) . . ?
O05 C22 C23 121.2(3) . 2_665 ?
O05 C22 C23 40.67(18) . . ?
C23 C22 C23 90.1(3) 2_665 . ?
O05 C22 H22A 107.0 . . ?
C23 C22 H22A 107.0 2_665 . ?
C23 C22 H22A 146.4 . . ?
O05 C22 H22B 107.0 . . ?
C23 C22 H22B 107.0 2_665 . ?
C23 C22 H22B 94.9 . . ?
H22A C22 H22B 106.8 . . ?
O05 C23 C22 120.9(3) . 2_665 ?
O05 C23 C22 40.6(2) . . ?
C22 C23 C22 89.9(3) 2_665 . ?
O05 C23 H23B 107.1 . . ?
C22 C23 H23B 107.1 2_665 . ?
C22 C23 H23B 95.0 . . ?
O05 C23 H23A 107.1 . . ?
C22 C23 H23A 107.1 2_665 . ?
C22 C23 H23A 146.3 . . ?
H23B C23 H23A 106.8 . . ?
C22 O05 C23 98.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 O04 C18 C17 -175.88(17) . . . . ?
C21 O04 C18 C19 4.0(3) . . . . ?
O04 C18 C17 C16 178.68(17) . . . . ?
C19 C18 C17 C16 -1.2(3) . . . . ?
C18 C17 C16 C15 0.4(3) . . . . ?
C17 C16 C15 C20 0.9(3) . . . . ?
C17 C16 C15 C14 179.92(18) . . . . ?
C20 C15 C14 C13 -179.28(18) . . . . ?
C16 C15 C14 C13 1.7(3) . . . . ?
C15 C14 C13 C12 -177.41(18) . . . . ?
B1 O03 C12 C11 -10.1(3) . . . . ?
B1 O03 C12 C13 170.67(17) . . . . ?
C14 C13 C12 O03 -1.5(3) . . . . ?
C14 C13 C12 C11 179.28(17) . . . . ?
O03 C12 C11 C10 -3.7(3) . . . . ?
C13 C12 C11 C10 175.56(17) . . . . ?
B1 O02 C10 C11 7.1(3) . . . . ?
B1 O02 C10 C09 -173.80(16) . . . . ?
C12 C11 C10 O02 5.2(3) . . . . ?
C12 C11 C10 C09 -173.88(17) . . . . ?
O02 C10 C09 C08 4.7(3) . . . . ?
C11 C10 C09 C08 -176.25(18) . . . . ?
C10 C09 C08 C05 -179.13(17) . . . . ?
C09 C08 C05 C06 -171.47(19) . . . . ?
C09 C08 C05 C04 9.0(3) . . . . ?
C04 C05 C06 C07 -0.5(3) . . . . ?
C08 C05 C06 C07 179.95(16) . . . . ?
C05 C06 C07 C02 0.0(3) . . . . ?
C01 O01 C02 C07 -0.3(3) . . . . ?
C01 O01 C02 C03 179.31(17) . . . . ?
C06 C07 C02 O01 -179.84(16) . . . . ?
C06 C07 C02 C03 0.6(3) . . . . ?
O04 C18 C19 C20 -179.21(18) . . . . ?
C17 C18 C19 C20 0.7(3) . . . . ?
C18 C19 C20 C15 0.7(3) . . . . ?
C16 C15 C20 C19 -1.5(3) . . . . ?
C14 C15 C20 C19 179.47(17) . . . . ?
O01 C02 C03 C04 179.77(16) . . . . ?
C07 C02 C03 C04 -0.6(3) . . . . ?
C02 C03 C04 C05 0.1(3) . . . . ?
C06 C05 C04 C03 0.5(3) . . . . ?
C08 C05 C04 C03 -179.99(17) . . . . ?
C12 O03 B1 F2 140.0(2) . . . . ?
C12 O03 B1 F1 -99.9(2) . . . . ?
C12 O03 B1 O02 20.1(3) . . . . ?
C10 O02 B1 F2 -137.97(19) . . . . ?
C10 O02 B1 F1 101.7(3) . . . . ?
C10 O02 B1 O03 -18.7(3) . . . . ?
C23 C22 C23 O05 142.3(4) 2_665 . . . ?
O05 C22 C23 C22 -142.3(4) . . . 2_665 ?
C23 C22 C23 C22 0.002(2) 2_665 . . 2_665 ?
C23 C22 O05 C23 -45.6(5) 2_665 . . . ?
C22 C23 O05 C22 45.4(5) 2_665 . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C21 H21C F2 0.98 2.47 3.094(8) 121.1 1_645 yes
C13 H13 F1 0.95 2.51 3.144(8) 124.1 2_666 yes
C01 H01B F2 0.98 2.57 3.323(7) 133.2 2_576 yes
C21 H21C F2 0.98 2.47 3.094(8) 121.1 1_645 yes
C13 H13 F1 0.95 2.51 3.144(8) 124.1 2_666 yes
C01 H01B F2 0.98 2.57 3.323(7) 133.2 2_576 yes

_refine_diff_density_max         0.245
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.055


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: tetrahydrofuran'
_exptl_crystal_preparation       Luminescent
