# 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_str1578
_database_code_depnum_ccdc_archive 'CCDC 1454643'
_audit_update_record             
;
2016-02-18 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;
_audit_creation_date             2014-10-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H16 O3, B F4'
_chemical_formula_sum            'C24 H17 B F4 O3'
_chemical_formula_weight         440.18
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H17 B F4 O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.1387(3)
_cell_length_b                   16.6302(5)
_cell_length_c                   17.1016(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.004(4)
_cell_angle_gamma                90
_cell_volume                     1999.39(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6560
_cell_measurement_temperature    148(80)
_cell_measurement_theta_max      64.6440
_cell_measurement_theta_min      3.7030
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.023
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.4568
_exptl_crystal_size_mid          0.0682
_exptl_crystal_size_min          0.0627
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.920
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15751
_diffrn_reflns_point_group_measured_fraction_full 0.920
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         64.783
_diffrn_reflns_theta_min         3.735
_diffrn_ambient_temperature      148(80)
_diffrn_detector_area_resol_mean 10.4051
_diffrn_measured_fraction_theta_full 0.920
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -48.00   42.00   0.6000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057   37.0000  -90.0000 150

#__ type_ start__ end____ width___ exp.time_
  2 omega  100.00  127.60   0.6000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       37.6057  178.0000  150.0000 46

#__ type_ start__ end____ width___ exp.time_
  3 omega   57.00  123.00   0.6000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       37.6057  178.0000   90.0000 110

#__ type_ start__ end____ width___ exp.time_
  4 omega  -41.00    0.40   0.6000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -68.5000   30.0000 -120.0000 69

#__ type_ start__ end____ width___ exp.time_
  5 omega    9.00  128.40   0.6000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       92.3754  -77.0000   30.0000 199

#__ type_ start__ end____ width___ exp.time_
  6 omega   41.00   98.00   0.6000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       92.3754  -45.0000  120.0000 95

#__ type_ start__ end____ width___ exp.time_
  7 omega   95.00  170.60   0.6000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       92.3754  125.0000   60.0000 126

#__ type_ start__ end____ width___ exp.time_
  8 omega  104.00  170.60   0.6000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       92.3754  125.0000    0.0000 111

#__ type_ start__ end____ width___ exp.time_
  9 omega   63.00  140.40   0.6000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       92.3754   77.0000  -30.0000 129

#__ type_ start__ end____ width___ exp.time_
 10 omega -116.00   -5.00   0.6000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  -57.0000 -180.0000 185

#__ type_ start__ end____ width___ exp.time_
 11 omega -116.00   -5.00   0.6000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  -57.0000  -60.0000 185

#__ type_ start__ end____ width___ exp.time_
 12 omega   54.00  174.00   0.6000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       92.3754   30.0000  150.0000 200

#__ type_ start__ end____ width___ exp.time_
 13 omega   60.00  171.00   0.6000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       92.3754   61.0000   30.0000 185

#__ type_ start__ end____ width___ exp.time_
 14 omega   60.00  171.00   0.6000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       92.3754   61.0000  -60.0000 185

#__ type_ start__ end____ width___ exp.time_
 15 omega   61.00  170.80   0.6000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       92.3754   45.0000 -120.0000 183

#__ type_ start__ end____ width___ exp.time_
 16 omega -115.00  -64.00   0.6000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057 -142.0000  -25.0000 85

#__ type_ start__ end____ width___ exp.time_
 17 omega -116.00   -5.00   0.6000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  -57.0000   60.0000 185

#__ type_ start__ end____ width___ exp.time_
 18 omega   23.00   65.60   0.6000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       92.3754 -125.0000   30.0000 71
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0223948000
_diffrn_orient_matrix_UB_12      -0.0038821000
_diffrn_orient_matrix_UB_13      -0.0912167000
_diffrn_orient_matrix_UB_21      -0.0709364000
_diffrn_orient_matrix_UB_22      -0.0873767000
_diffrn_orient_matrix_UB_23      0.0014310000
_diffrn_orient_matrix_UB_31      -0.2060255000
_diffrn_orient_matrix_UB_32      0.0304734000
_diffrn_orient_matrix_UB_33      -0.0075401000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2810
_reflns_number_total             3341
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.80
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         3341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0442
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0782P)²+0.5492P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1275
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O1 O 0.42875(17) 0.66826(7) 0.50670(7) 0.0293(3) Uani 1 1 d . . . . .
F3 F 0.9430(3) 0.59374(11) 0.81909(9) 0.0911(6) Uani 1 1 d . . . . .
O3 O 0.0843(2) 0.60705(8) -0.02880(7) 0.0418(4) Uani 1 1 d . . . . .
F1 F 0.7752(2) 0.59604(10) 0.69633(7) 0.0711(5) Uani 1 1 d . . . . .
O2 O 0.0485(2) 0.74031(8) -0.02945(8) 0.0435(4) Uani 1 1 d . . . . .
F4 F 0.7708(3) 0.70357(8) 0.77818(9) 0.0813(5) Uani 1 1 d . . . . .
F2 F 0.6241(3) 0.59019(11) 0.80047(11) 0.0967(7) Uani 1 1 d . . . . .
C1 C 0.1586(2) 0.67516(10) 0.09389(10) 0.0296(4) Uani 1 1 d . . . . .
C8 C 0.2975(2) 0.54056(10) 0.52285(10) 0.0286(4) Uani 1 1 d . . . . .
C20 C 0.4760(2) 0.73354(10) 0.46756(10) 0.0290(4) Uani 1 1 d . . . . .
C19 C 0.5712(2) 0.79561(10) 0.52020(10) 0.0292(4) Uani 1 1 d . . . . .
C7 C 0.3384(2) 0.60417(10) 0.46913(10) 0.0289(4) Uani 1 1 d . . . . .
C24 C 0.0907(3) 0.67850(10) 0.00627(10) 0.0310(4) Uani 1 1 d . . . . .
C4 C 0.2768(3) 0.67359(10) 0.25763(10) 0.0311(4) Uani 1 1 d . . . . .
C5 C 0.3342(3) 0.67186(10) 0.34492(10) 0.0313(4) Uani 1 1 d . . . . .
C13 C 0.3316(3) 0.55172(11) 0.60502(10) 0.0363(4) Uani 1 1 d . . . . .
C9 C 0.2220(3) 0.46722(10) 0.49138(11) 0.0334(4) Uani 1 1 d . . . . .
C21 C 0.4302(3) 0.73601(10) 0.38638(10) 0.0325(4) Uani 1 1 d . . . . .
C6 C 0.2904(3) 0.60497(11) 0.38826(10) 0.0317(4) Uani 1 1 d . . . . .
C22 C 0.2197(3) 0.74588(11) 0.21856(11) 0.0349(4) Uani 1 1 d . . . . .
C14 C 0.6357(3) 0.77994(11) 0.60065(11) 0.0347(4) Uani 1 1 d . . . . .
C2 C 0.2162(3) 0.60331(11) 0.13240(11) 0.0329(4) Uani 1 1 d . . . . .
C23 C 0.1592(3) 0.74576(11) 0.13729(11) 0.0341(4) Uani 1 1 d . . . . .
C3 C 0.2742(3) 0.60264(11) 0.21397(11) 0.0344(4) Uani 1 1 d . . . . .
C18 C 0.5940(3) 0.87280(11) 0.49076(11) 0.0373(4) Uani 1 1 d . . . . .
C10 C 0.1798(3) 0.40726(11) 0.54158(13) 0.0397(5) Uani 1 1 d . . . . .
C15 C 0.7182(3) 0.84028(12) 0.65017(11) 0.0392(4) Uani 1 1 d . . . . .
C17 C 0.6784(3) 0.93249(12) 0.54109(12) 0.0423(5) Uani 1 1 d . . . . .
C12 C 0.2873(3) 0.49138(13) 0.65450(12) 0.0441(5) Uani 1 1 d . . . . .
C16 C 0.7393(3) 0.91682(12) 0.62056(12) 0.0402(5) Uani 1 1 d . . . . .
C11 C 0.2112(3) 0.41940(13) 0.62278(13) 0.0443(5) Uani 1 1 d . . . . .
B1 B 0.7777(4) 0.62208(14) 0.77263(12) 0.0451(6) Uani 1 1 d . . . . .
H6 H 0.227(3) 0.5604(13) 0.3616(12) 0.036(5) Uiso 1 1 d . . . . .
H21 H 0.468(3) 0.7834(14) 0.3581(13) 0.042(5) Uiso 1 1 d . . . . .
H23 H 0.118(3) 0.7943(14) 0.1101(13) 0.045(6) Uiso 1 1 d . . . . .
H2 H 0.216(3) 0.5533(13) 0.1015(12) 0.038(5) Uiso 1 1 d . . . . .
H9 H 0.198(3) 0.4590(13) 0.4358(13) 0.039(5) Uiso 1 1 d . . . . .
H13 H 0.390(3) 0.6044(14) 0.6288(13) 0.047(6) Uiso 1 1 d . . . . .
H12 H 0.313(3) 0.5002(13) 0.7154(14) 0.048(6) Uiso 1 1 d . . . . .
H14 H 0.625(3) 0.7258(14) 0.6220(12) 0.040(5) Uiso 1 1 d . . . . .
H18 H 0.551(3) 0.8835(14) 0.4362(15) 0.047(6) Uiso 1 1 d . . . . .
H22 H 0.217(3) 0.7968(14) 0.2497(13) 0.051(6) Uiso 1 1 d . . . . .
H10 H 0.126(3) 0.3581(15) 0.5203(13) 0.047(6) Uiso 1 1 d . . . . .
H16 H 0.802(3) 0.9597(14) 0.6579(13) 0.046(6) Uiso 1 1 d . . . . .
H11 H 0.191(3) 0.3739(15) 0.6575(14) 0.052(6) Uiso 1 1 d . . . . .
H3 H 0.317(3) 0.5526(15) 0.2406(13) 0.047(6) Uiso 1 1 d . . . . .
H17 H 0.697(4) 0.9864(16) 0.5190(14) 0.059(7) Uiso 1 1 d . . . . .
H15 H 0.767(3) 0.8273(14) 0.7047(15) 0.050(6) Uiso 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
O1 C20 1.349(2) . ?
O1 C7 1.349(2) . ?
F3 B1 1.386(3) . ?
O3 C24 1.328(2) . ?
F1 B1 1.372(3) . ?
O2 C24 1.207(2) . ?
F4 B1 1.360(3) . ?
F2 B1 1.375(3) . ?
C1 C24 1.494(2) . ?
C1 C2 1.391(2) . ?
C1 C23 1.389(2) . ?
C8 C7 1.463(2) . ?
C8 C13 1.396(3) . ?
C8 C9 1.403(2) . ?
C20 C19 1.458(2) . ?
C20 C21 1.371(2) . ?
C19 C14 1.397(3) . ?
C19 C18 1.399(2) . ?
C7 C6 1.366(3) . ?
C4 C5 1.478(2) . ?
C4 C22 1.401(3) . ?
C4 C3 1.395(2) . ?
C5 C21 1.393(3) . ?
C5 C6 1.402(2) . ?
C13 C12 1.384(3) . ?
C9 C10 1.383(3) . ?
C22 C23 1.382(3) . ?
C14 C15 1.378(3) . ?
C2 C3 1.384(3) . ?
C18 C17 1.382(3) . ?
C10 C11 1.382(3) . ?
C15 C16 1.388(3) . ?
C17 C16 1.378(3) . ?
C12 C11 1.386(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
C20 O1 C7 122.65(13) . . ?
C2 C1 C24 121.63(15) . . ?
C23 C1 C24 118.36(15) . . ?
C23 C1 C2 119.99(16) . . ?
C13 C8 C7 121.12(16) . . ?
C13 C8 C9 119.34(16) . . ?
C9 C8 C7 119.53(15) . . ?
O1 C20 C19 113.17(14) . . ?
O1 C20 C21 119.40(15) . . ?
C21 C20 C19 127.43(15) . . ?
C14 C19 C20 120.96(15) . . ?
C14 C19 C18 119.11(16) . . ?
C18 C19 C20 119.90(15) . . ?
O1 C7 C8 113.76(14) . . ?
O1 C7 C6 119.31(15) . . ?
C6 C7 C8 126.91(16) . . ?
O3 C24 C1 113.55(14) . . ?
O2 C24 O3 123.18(16) . . ?
O2 C24 C1 123.26(16) . . ?
C22 C4 C5 120.32(15) . . ?
C3 C4 C5 119.99(15) . . ?
C3 C4 C22 119.66(16) . . ?
C21 C5 C4 121.64(15) . . ?
C21 C5 C6 118.27(16) . . ?
C6 C5 C4 120.08(16) . . ?
C12 C13 C8 120.03(18) . . ?
C10 C9 C8 119.97(18) . . ?
C20 C21 C5 120.14(16) . . ?
C7 C6 C5 120.22(16) . . ?
C23 C22 C4 119.51(16) . . ?
C15 C14 C19 120.13(17) . . ?
C3 C2 C1 119.72(16) . . ?
C22 C23 C1 120.68(16) . . ?
C2 C3 C4 120.43(16) . . ?
C17 C18 C19 120.04(17) . . ?
C11 C10 C9 120.24(18) . . ?
C14 C15 C16 120.37(18) . . ?
C16 C17 C18 120.48(18) . . ?
C13 C12 C11 120.18(18) . . ?
C17 C16 C15 119.86(18) . . ?
C10 C11 C12 120.23(17) . . ?
F1 B1 F3 107.9(2) . . ?
F1 B1 F2 109.2(2) . . ?
F4 B1 F3 109.7(2) . . ?
F4 B1 F1 112.72(18) . . ?
F4 B1 F2 108.6(2) . . ?
F2 B1 F3 108.7(2) . . ?

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
O1 C20 C19 C14 11.2(2) . . . . ?
O1 C20 C19 C18 -166.86(16) . . . . ?
O1 C20 C21 C5 0.6(3) . . . . ?
O1 C7 C6 C5 -0.2(3) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C8 C7 C6 C5 177.82(17) . . . . ?
C8 C13 C12 C11 0.8(3) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C20 O1 C7 C8 -178.91(15) . . . . ?
C20 O1 C7 C6 -0.6(2) . . . . ?
C20 C19 C14 C15 -177.24(17) . . . . ?
C20 C19 C18 C17 177.80(18) . . . . ?
C19 C20 C21 C5 -178.36(17) . . . . ?
C19 C14 C15 C16 -0.5(3) . . . . ?
C19 C18 C17 C16 -0.6(3) . . . . ?
C7 O1 C20 C19 179.54(14) . . . . ?
C7 O1 C20 C21 0.4(2) . . . . ?
C7 C8 C13 C12 178.39(18) . . . . ?
C7 C8 C9 C10 -178.91(17) . . . . ?
C24 C1 C2 C3 -178.56(17) . . . . ?
C24 C1 C23 C22 179.65(17) . . . . ?
C4 C5 C21 C20 177.92(17) . . . . ?
C4 C5 C6 C7 -178.13(16) . . . . ?
C4 C22 C23 C1 -1.5(3) . . . . ?
C5 C4 C22 C23 -177.40(17) . . . . ?
C5 C4 C3 C2 178.43(17) . . . . ?
C13 C8 C7 O1 6.9(2) . . . . ?
C13 C8 C7 C6 -171.26(18) . . . . ?
C13 C8 C9 C10 0.8(3) . . . . ?
C13 C12 C11 C10 0.3(3) . . . . ?
C9 C8 C7 O1 -173.42(15) . . . . ?
C9 C8 C7 C6 8.5(3) . . . . ?
C9 C8 C13 C12 -1.3(3) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C21 C20 C19 C14 -169.74(18) . . . . ?
C21 C20 C19 C18 12.2(3) . . . . ?
C21 C5 C6 C7 1.2(3) . . . . ?
C6 C5 C21 C20 -1.4(3) . . . . ?
C22 C4 C5 C21 -34.9(3) . . . . ?
C22 C4 C5 C6 144.34(19) . . . . ?
C22 C4 C3 C2 0.2(3) . . . . ?
C14 C19 C18 C17 -0.3(3) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C2 C1 C24 O3 2.6(3) . . . . ?
C2 C1 C24 O2 -176.32(18) . . . . ?
C2 C1 C23 C22 1.1(3) . . . . ?
C23 C1 C24 O3 -175.90(16) . . . . ?
C23 C1 C24 O2 5.2(3) . . . . ?
C23 C1 C2 C3 -0.1(3) . . . . ?
C3 C4 C5 C21 146.88(19) . . . . ?
C3 C4 C5 C6 -33.8(3) . . . . ?
C3 C4 C22 C23 0.8(3) . . . . ?
C18 C19 C14 C15 0.9(3) . . . . ?
C18 C17 C16 C15 0.9(3) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 -1 -11 0.0282 -0.0021 -0.9843 -10.9987 1.0071 0.0704 0.0534
-4 3 0 0.2258 -3.9988 2.9993 0.0101 0.0770 0.0216 0.9152
4 -3 0 0.2258 3.9988 -2.9993 -0.0101 -0.0770 -0.0216 -0.9152
1 11 -1 0.0322 1.0072 10.9960 -1.0018 0.0261 -1.0337 0.1351
0 1 11 0.0399 0.0021 0.9843 10.9987 -1.0071 -0.0704 -0.0534
-4 -4 -6 0.2048 -4.0041 -3.9890 -5.9895 0.6515 0.6240 0.7486
0 -11 1 0.0488 -0.0070 -10.9962 0.9993 -0.0483 0.9627 -0.3412
0 11 0 0.0179 0.0072 10.9948 0.0005 -0.0429 -0.9612 0.3336
0 0 -11 0.0185 -0.0015 0.0152 -10.9986 1.0032 -0.0170 0.0837
-1 1 11 0.0300 -0.9981 0.9845 11.0011 -0.9850 0.0005 0.1527
-1 -10 3 0.0368 -1.0063 -9.9992 3.0016 -0.2124 0.9494 -0.1200
-1 -10 3 0.0368 -1.0063 -9.9992 3.0016 -0.2124 0.9494 -0.1200
-1 -10 3 0.0368 -1.0063 -9.9992 3.0016 -0.2124 0.9494 -0.1200

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_str1520
_database_code_depnum_ccdc_archive 'CCDC 1454644'
_audit_update_record             
;
2016-02-18 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;
_audit_creation_date             2014-10-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H16 Br O, B F4'
_chemical_formula_sum            'C23 H16 B Br F4 O'
_chemical_formula_weight         475.08
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H16 B F4 O Br'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.5265(4)
_cell_length_b                   9.8137(3)
_cell_length_c                   15.2162(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.234(3)
_cell_angle_gamma                90
_cell_volume                     2011.44(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6897
_cell_measurement_temperature    298
_cell_measurement_theta_max      71.7740
_cell_measurement_theta_min      4.1640
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.225
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             952
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.295
_exptl_crystal_size_mid          0.041
_exptl_crystal_size_min          0.034
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0879
_diffrn_reflns_av_unetI/netI     0.0905
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18214
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.748
_diffrn_reflns_theta_min         4.188
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 10.4051
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9852
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -61.00   30.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057   57.0000 -180.0000 91

#__ type_ start__ end____ width___ exp.time_
  2 omega  -48.00   -2.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057   37.0000  150.0000 46

#__ type_ start__ end____ width___ exp.time_
  3 omega  -37.00   38.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057   37.0000   60.0000 75

#__ type_ start__ end____ width___ exp.time_
  4 omega   39.00   66.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       37.6057 -107.0000 -101.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega -119.00  -81.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -68.5000 -111.0000 -180.0000 38

#__ type_ start__ end____ width___ exp.time_
  6 omega   54.00  107.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3308  -94.0000  -30.0000 53

#__ type_ start__ end____ width___ exp.time_
  7 omega  148.00  178.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3308  111.0000  -60.0000 30

#__ type_ start__ end____ width___ exp.time_
  8 omega   30.00   77.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3308  -30.0000 -150.0000 47

#__ type_ start__ end____ width___ exp.time_
  9 omega  153.00  178.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3308  107.0000   -3.0000 25

#__ type_ start__ end____ width___ exp.time_
 10 omega  121.00  148.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3308  107.0000   -3.0000 27

#__ type_ start__ end____ width___ exp.time_
 11 omega   51.00   99.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3308  -45.0000  150.0000 48

#__ type_ start__ end____ width___ exp.time_
 12 omega   36.00   63.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3308  -30.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 13 omega   39.00   92.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3308  -45.0000   90.0000 53

#__ type_ start__ end____ width___ exp.time_
 14 omega   23.00  177.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3308  -15.0000  -90.0000 154

#__ type_ start__ end____ width___ exp.time_
 15 omega -116.00   -5.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  -57.0000  -60.0000 111

#__ type_ start__ end____ width___ exp.time_
 16 omega -116.00   -5.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  -57.0000   60.0000 111

#__ type_ start__ end____ width___ exp.time_
 17 omega -116.00   -5.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  -57.0000 -180.0000 111

#__ type_ start__ end____ width___ exp.time_
 18 omega   55.00  129.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       37.6057 -178.0000   30.0000 74

#__ type_ start__ end____ width___ exp.time_
 19 omega -153.00  -86.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -68.5000  -77.0000 -120.0000 67

#__ type_ start__ end____ width___ exp.time_
 20 omega   70.00  178.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3308   30.0000   90.0000 108

#__ type_ start__ end____ width___ exp.time_
 21 omega   30.00   99.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3308  -45.0000   30.0000 69

#__ type_ start__ end____ width___ exp.time_
 22 omega   72.00  178.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3308   77.0000   90.0000 106

#__ type_ start__ end____ width___ exp.time_
 23 omega   70.00  178.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3308   30.0000    0.0000 108

#__ type_ start__ end____ width___ exp.time_
 24 omega   27.00  115.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3308 -111.0000   90.0000 88

#__ type_ start__ end____ width___ exp.time_
 25 omega   72.00  178.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3308   77.0000  -90.0000 106

#__ type_ start__ end____ width___ exp.time_
 26 omega   72.00  178.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3308   77.0000  150.0000 106
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0715132000
_diffrn_orient_matrix_UB_12      0.0695102000
_diffrn_orient_matrix_UB_13      -0.0592709000
_diffrn_orient_matrix_UB_21      0.0799546000
_diffrn_orient_matrix_UB_22      0.0075545000
_diffrn_orient_matrix_UB_23      0.0787188000
_diffrn_orient_matrix_UB_31      0.0396482000
_diffrn_orient_matrix_UB_32      -0.1405505000
_diffrn_orient_matrix_UB_33      -0.0250619000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2849
_reflns_number_total             3939
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_refine_diff_density_max         1.140
_refine_diff_density_min         -0.815
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.439
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3939
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1292
_refine_ls_R_factor_gt           0.0740
_refine_ls_restrained_S_all      1.439
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1377P)²+2.5801P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2916
_refine_ls_wR_factor_ref         0.3051
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H22(0.057) H23(0.064) H9(0.057) H13(0.056) H6(0.05) H15(0.066)
 H2(0.065) H14(0.062) H21(0.054) H11(0.062) H10(0.062) H16(0.064) H12(0.062)
 H18(0.062) H3(0.062) H17(0.07)
 Fixed X: H22(0.2033) H23(0.2925) H9(-0.129) H13(-0.1623) H6(-0.0142) H15(-
 0.0597) H2(0.1508) H14(-0.0473) H21(0.1224) H11(-0.318) H10(-0.2434)
 H16(0.0009) H12(-0.2792) H18(0.0818) H3(0.0607) H17(0.0733)
 Fixed Y: H22(-0.0158) H23(-0.157) H9(0.4071) H13(0.5147) H6(0.2664)
 H15(0.4353) H2(0.0014) H14(0.4369) H21(0.1072) H11(0.7053) H10(0.5719)
 H16(0.2542) H12(0.6753) H18(0.0677) H3(0.141) H17(0.0732)
 Fixed Z: H22(0.598) H23(0.5128) H9(0.4) H13(0.6514) H6(0.4507) H15(0.945)
 H2(0.2931) H14(0.7942) H21(0.6737) H11(0.451) H10(0.3511) H16(1.0299)
 H12(0.6003) H18(0.8136) H3(0.3784) H17(0.9648)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br1 Br 0.30454(6) -0.20295(9) 0.32554(5) 0.0639(4) Uani 1 1 d . . . . .
F2 F 0.5182(3) -0.1582(5) 0.2047(3) 0.0624(12) Uani 1 1 d . . . . .
O1 O -0.0457(3) 0.3349(5) 0.6510(3) 0.0402(10) Uani 1 1 d . . . . .
F4 F 0.5420(6) -0.2999(8) 0.3215(4) 0.116(3) Uani 1 1 d . . . . .
F3 F 0.6606(6) -0.1529(8) 0.2914(6) 0.144(4) Uani 1 1 d . . . . .
F1 F 0.6252(5) -0.3316(7) 0.2072(4) 0.0977(19) Uani 1 1 d . . . . .
C22 C 0.1926(5) -0.0119(8) 0.5368(4) 0.0475(15) Uani 1 1 d . . . . .
H22 H 0.2033 -0.0158 0.5980 0.057 Uiso 1 1 calc R U . . .
C23 C 0.2461(5) -0.0966(9) 0.4860(5) 0.0531(17) Uani 1 1 d . . . . .
H23 H 0.2925 -0.1570 0.5128 0.064 Uiso 1 1 calc R U . . .
C1 C 0.2300(5) -0.0905(7) 0.3952(4) 0.0458(15) Uani 1 1 d . . . . .
C9 C -0.1582(5) 0.4616(8) 0.4405(4) 0.0471(15) Uani 1 1 d . . . . .
H9 H -0.1290 0.4071 0.4000 0.057 Uiso 1 1 calc R U . . .
C13 C -0.1785(5) 0.5256(7) 0.5911(4) 0.0469(15) Uani 1 1 d . . . . .
H13 H -0.1623 0.5147 0.6514 0.056 Uiso 1 1 calc R U . . .
C7 C -0.0587(5) 0.3433(7) 0.5618(4) 0.0397(14) Uani 1 1 d . . . . .
C20 C 0.0201(5) 0.2477(7) 0.6920(4) 0.0401(13) Uani 1 1 d . . . . .
C8 C -0.1326(4) 0.4447(7) 0.5310(4) 0.0398(13) Uani 1 1 d . . . . .
C4 C 0.1226(4) 0.0795(7) 0.4976(4) 0.0420(14) Uani 1 1 d . . . . .
C6 C -0.0048(5) 0.2610(7) 0.5119(4) 0.0416(14) Uani 1 1 d . . . . .
H6 H -0.0142 0.2664 0.4507 0.050 Uiso 1 1 calc R U . . .
C5 C 0.0646(5) 0.1685(7) 0.5513(4) 0.0408(14) Uani 1 1 d . . . . .
C15 C -0.0306(6) 0.3620(9) 0.9184(4) 0.0552(18) Uani 1 1 d . . . . .
H15 H -0.0597 0.4353 0.9450 0.066 Uiso 1 1 calc R U . . .
C19 C 0.0176(5) 0.2521(7) 0.7883(4) 0.0436(14) Uani 1 1 d . . . . .
C2 C 0.1611(5) -0.0020(8) 0.3544(5) 0.0541(17) Uani 1 1 d . . . . .
H2 H 0.1508 0.0014 0.2931 0.065 Uiso 1 1 calc R U . . .
C14 C -0.0240(6) 0.3626(8) 0.8280(4) 0.0514(16) Uani 1 1 d . . . . .
H14 H -0.0473 0.4369 0.7942 0.062 Uiso 1 1 calc R U . . .
C21 C 0.0761(5) 0.1657(7) 0.6446(4) 0.0453(15) Uani 1 1 d . . . . .
H21 H 0.1224 0.1072 0.6737 0.054 Uiso 1 1 calc R U . . .
C11 C -0.2718(5) 0.6395(8) 0.4711(5) 0.0517(17) Uani 1 1 d . . . . .
H11 H -0.3180 0.7053 0.4510 0.062 Uiso 1 1 calc R U . . .
C10 C -0.2271(5) 0.5597(8) 0.4113(4) 0.0513(17) Uani 1 1 d . . . . .
H10 H -0.2434 0.5719 0.3511 0.062 Uiso 1 1 calc R U . . .
C16 C 0.0055(5) 0.2538(9) 0.9693(4) 0.0536(17) Uani 1 1 d . . . . .
H16 H 0.0009 0.2542 1.0299 0.064 Uiso 1 1 calc R U . . .
C12 C -0.2482(5) 0.6221(8) 0.5604(5) 0.0519(17) Uani 1 1 d . . . . .
H12 H -0.2792 0.6753 0.6003 0.062 Uiso 1 1 calc R U . . .
C18 C 0.0539(6) 0.1424(8) 0.8397(4) 0.0518(17) Uani 1 1 d . . . . .
H18 H 0.0818 0.0677 0.8136 0.062 Uiso 1 1 calc R U . . .
C3 C 0.1076(6) 0.0818(8) 0.4057(4) 0.0518(17) Uani 1 1 d . . . . .
H3 H 0.0607 0.1410 0.3784 0.062 Uiso 1 1 calc R U . . .
B1 B 0.5875(6) -0.2321(10) 0.2585(5) 0.053(2) Uani 1 1 d . . . . .
C17 C 0.0480(6) 0.1455(9) 0.9302(5) 0.0584(19) Uani 1 1 d . . . . .
H17 H 0.0733 0.0732 0.9648 0.070 Uiso 1 1 calc R U . . .


_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
Br1 C1 1.884(6) . ?
F2 B1 1.392(9) . ?
O1 C7 1.355(7) . ?
O1 C20 1.346(8) . ?
F4 B1 1.359(11) . ?
F3 B1 1.321(12) . ?
F1 B1 1.378(10) . ?
C22 C23 1.384(10) . ?
C22 C4 1.398(9) . ?
C23 C1 1.381(9) . ?
C1 C2 1.380(10) . ?
C9 C8 1.400(8) . ?
C9 C10 1.385(10) . ?
C13 C8 1.398(9) . ?
C13 C12 1.388(9) . ?
C7 C8 1.457(9) . ?
C7 C6 1.365(9) . ?
C20 C19 1.470(8) . ?
C20 C21 1.357(10) . ?
C4 C5 1.472(9) . ?
C4 C3 1.394(9) . ?
C6 C5 1.401(9) . ?
C5 C21 1.414(9) . ?
C15 C14 1.387(9) . ?
C15 C16 1.376(11) . ?
C19 C14 1.386(10) . ?
C19 C18 1.394(10) . ?
C2 C3 1.383(10) . ?
C11 C10 1.381(11) . ?
C11 C12 1.378(10) . ?
C16 C17 1.370(12) . ?
C18 C17 1.386(9) . ?

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
C20 O1 C7 121.5(5) . . ?
C23 C22 C4 121.0(6) . . ?
C1 C23 C22 119.4(7) . . ?
C23 C1 Br1 119.6(5) . . ?
C2 C1 Br1 119.3(5) . . ?
C2 C1 C23 121.1(6) . . ?
C10 C9 C8 119.8(7) . . ?
C12 C13 C8 119.7(6) . . ?
O1 C7 C8 112.7(5) . . ?
O1 C7 C6 119.6(6) . . ?
C6 C7 C8 127.7(5) . . ?
O1 C20 C19 111.6(6) . . ?
O1 C20 C21 120.6(5) . . ?
C21 C20 C19 127.7(6) . . ?
C9 C8 C7 119.8(6) . . ?
C13 C8 C9 119.5(6) . . ?
C13 C8 C7 120.7(5) . . ?
C22 C4 C5 121.2(6) . . ?
C3 C4 C22 118.0(6) . . ?
C3 C4 C5 120.8(6) . . ?
C7 C6 C5 121.0(6) . . ?
C6 C5 C4 121.1(5) . . ?
C6 C5 C21 116.9(6) . . ?
C21 C5 C4 122.1(6) . . ?
C16 C15 C14 120.6(7) . . ?
C14 C19 C20 120.3(6) . . ?
C14 C19 C18 119.7(6) . . ?
C18 C19 C20 119.9(6) . . ?
C1 C2 C3 119.1(6) . . ?
C15 C14 C19 119.7(7) . . ?
C20 C21 C5 120.3(6) . . ?
C10 C11 C12 120.2(6) . . ?
C11 C10 C9 120.4(6) . . ?
C17 C16 C15 119.7(6) . . ?
C11 C12 C13 120.4(7) . . ?
C17 C18 C19 119.4(7) . . ?
C2 C3 C4 121.4(7) . . ?
F4 B1 F2 110.3(7) . . ?
F4 B1 F1 105.5(8) . . ?
F3 B1 F2 111.0(8) . . ?
F3 B1 F4 113.1(8) . . ?
F3 B1 F1 109.2(8) . . ?
F1 B1 F2 107.5(6) . . ?
C16 C17 C18 120.8(7) . . ?

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
Br1 C1 C2 C3 -179.0(6) . . . . ?
O1 C7 C8 C9 -177.0(6) . . . . ?
O1 C7 C8 C13 3.0(8) . . . . ?
O1 C7 C6 C5 -0.6(10) . . . . ?
O1 C20 C19 C14 -18.8(9) . . . . ?
O1 C20 C19 C18 158.9(6) . . . . ?
O1 C20 C21 C5 -1.4(10) . . . . ?
C22 C23 C1 Br1 178.7(5) . . . . ?
C22 C23 C1 C2 -0.3(11) . . . . ?
C22 C4 C5 C6 179.3(6) . . . . ?
C22 C4 C5 C21 -0.4(10) . . . . ?
C22 C4 C3 C2 -0.9(11) . . . . ?
C23 C22 C4 C5 179.2(6) . . . . ?
C23 C22 C4 C3 0.6(11) . . . . ?
C23 C1 C2 C3 0.0(11) . . . . ?
C1 C2 C3 C4 0.6(12) . . . . ?
C7 O1 C20 C19 -177.2(6) . . . . ?
C7 O1 C20 C21 0.5(9) . . . . ?
C7 C6 C5 C4 179.9(6) . . . . ?
C7 C6 C5 C21 -0.4(10) . . . . ?
C20 O1 C7 C8 -179.6(5) . . . . ?
C20 O1 C7 C6 0.6(9) . . . . ?
C20 C19 C14 C15 176.5(7) . . . . ?
C20 C19 C18 C17 -177.8(7) . . . . ?
C8 C9 C10 C11 -1.0(11) . . . . ?
C8 C13 C12 C11 -0.6(11) . . . . ?
C8 C7 C6 C5 179.6(6) . . . . ?
C4 C22 C23 C1 0.0(11) . . . . ?
C4 C5 C21 C20 -178.9(6) . . . . ?
C6 C7 C8 C9 2.8(10) . . . . ?
C6 C7 C8 C13 -177.1(7) . . . . ?
C6 C5 C21 C20 1.4(10) . . . . ?
C5 C4 C3 C2 -179.5(7) . . . . ?
C15 C16 C17 C18 -1.1(12) . . . . ?
C19 C20 C21 C5 175.8(7) . . . . ?
C19 C18 C17 C16 1.2(12) . . . . ?
C14 C15 C16 C17 -0.2(12) . . . . ?
C14 C19 C18 C17 -0.1(11) . . . . ?
C21 C20 C19 C14 163.7(7) . . . . ?
C21 C20 C19 C18 -18.6(11) . . . . ?
C10 C9 C8 C13 1.2(10) . . . . ?
C10 C9 C8 C7 -178.8(6) . . . . ?
C10 C11 C12 C13 0.9(11) . . . . ?
C16 C15 C14 C19 1.3(12) . . . . ?
C12 C13 C8 C9 -0.4(10) . . . . ?
C12 C13 C8 C7 179.6(6) . . . . ?
C12 C11 C10 C9 -0.1(11) . . . . ?
C18 C19 C14 C15 -1.1(11) . . . . ?
C3 C4 C5 C6 -2.1(10) . . . . ?
C3 C4 C5 C21 178.2(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
