# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_ad600
_database_code_depnum_ccdc_archive 'CCDC 1578963'
_audit_update_record             
;
2017-10-09 deposited with the CCDC.
2018-11-07 downloaded from the CCDC.
;

_audit_creation_date             2012-12-13T10:18:12-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H11 B1 Br1 Cl1 F2 O3'
_chemical_formula_sum            'C16 H11 B1 Br1 Cl1 F2 O3'
_chemical_formula_weight         415.42
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.5791(2)
_cell_length_b                   15.1383(4)
_cell_length_c                   14.0950(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.118(2)
_cell_angle_gamma                90
_cell_volume                     1592.04(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    16729
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      29.01
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    2.783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_absorpt_correction_T_min  0.694
_exptl_absorpt_correction_T_max  0.7

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.0713
_diffrn_reflns_number            16729
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.73
_diffrn_reflns_theta_max         29.01
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.952
_reflns_number_total             4043
_reflns_number_gt                2439
_reflns_threshold_expression     >2σ(I)
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

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

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

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0326P)²+0.9764P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4043
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1076
_refine_ls_wR_factor_gt          0.0951
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_restrained_S_all      1.02
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.991
_refine_diff_density_min         -0.856
_refine_diff_density_rms         0.069

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7733(4) 0.35354(19) 0.60235(19) 0.0364(7) Uani 1 1 d . . .
C2 C 0.6872(4) 0.3197(2) 0.51339(19) 0.0374(7) Uani 1 1 d . . .
C3 C 0.6848(4) 0.2312(2) 0.4940(2) 0.0413(7) Uani 1 1 d . . .
H3 H 0.6268 0.21 0.4347 0.05 Uiso 1 1 calc R . .
C4 C 0.7704(4) 0.1732(2) 0.5641(2) 0.0452(8) Uani 1 1 d . . .
C5 C 0.8541(4) 0.2024(2) 0.6524(2) 0.0424(7) Uani 1 1 d . . .
H5 H 0.9092 0.1626 0.6985 0.051 Uiso 1 1 calc R . .
C6 C 0.8559(4) 0.29310(19) 0.67243(18) 0.0349(7) Uani 1 1 d . . .
C7 C 0.9439(4) 0.3287(2) 0.7638(2) 0.0375(7) Uani 1 1 d . . .
C8 C 1.0236(4) 0.2749(2) 0.84302(19) 0.0413(7) Uani 1 1 d . . .
H8 H 1.0159 0.2137 0.838 0.05 Uiso 1 1 calc R . .
C9 C 1.1098(4) 0.3120(2) 0.9251(2) 0.0435(8) Uani 1 1 d . . .
H9 H 1.1151 0.3734 0.9257 0.052 Uiso 1 1 calc R . .
C10 C 1.1951(4) 0.2682(2) 1.01206(19) 0.0409(7) Uani 1 1 d . . .
C11 C 1.1943(4) 0.1772(2) 1.0247(2) 0.0426(7) Uani 1 1 d . . .
H11 H 1.1376 0.1418 0.9746 0.051 Uiso 1 1 calc R . .
C12 C 1.2754(4) 0.1380(2) 1.1096(2) 0.0449(8) Uani 1 1 d . . .
H12 H 1.2724 0.077 1.1169 0.054 Uiso 1 1 calc R . .
C13 C 1.3619(4) 0.1913(2) 1.1843(2) 0.0451(8) Uani 1 1 d . . .
C14 C 1.3635(5) 0.2821(2) 1.1739(2) 0.0536(9) Uani 1 1 d . . .
H14 H 1.4201 0.3174 1.2242 0.064 Uiso 1 1 calc R . .
C15 C 1.2813(5) 0.3201(2) 1.0891(2) 0.0504(9) Uani 1 1 d . . .
H15 H 1.2828 0.3812 1.0826 0.06 Uiso 1 1 calc R . .
C16 C 1.4325(6) 0.0676(3) 1.2899(3) 0.0682(11) Uani 1 1 d . . .
H16A H 1.3085 0.0517 1.2847 0.102 Uiso 1 1 calc R . .
H16B H 1.4945 0.055 1.3538 0.102 Uiso 1 1 calc R . .
H16C H 1.4851 0.0341 1.2441 0.102 Uiso 1 1 calc R . .
O1 O 0.7719(3) 0.43960(14) 0.61748(15) 0.0549(6) Uani 1 1 d . . .
O2 O 0.9517(3) 0.41313(14) 0.77575(15) 0.0520(6) Uani 1 1 d . . .
O3 O 1.4463(3) 0.15944(17) 1.27055(15) 0.0591(7) Uani 1 1 d . . .
F1 F 1.0223(3) 0.52455(15) 0.67566(16) 0.0706(6) Uani 1 1 d . . .
F2 F 0.7783(3) 0.53836(15) 0.74216(15) 0.0729(7) Uani 1 1 d . . .
Cl1 Cl 0.77461(19) 0.06170(6) 0.53587(7) 0.0864(4) Uani 1 1 d . . .
Br1 Br 0.56951(5) 0.39798(2) 0.41977(2) 0.05898(15) Uani 1 1 d . . .
B1 B 0.8799(6) 0.4812(2) 0.7006(3) 0.0484(10) Uani 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.320(4) . ?
C1 C2 1.405(4) . ?
C1 C6 1.410(4) . ?
C2 C3 1.366(4) . ?
C2 Br1 1.878(3) . ?
C3 C4 1.394(4) . ?
C3 H3 0.93 . ?
C4 C5 1.367(4) . ?
C4 Cl1 1.736(3) . ?
C5 C6 1.402(4) . ?
C5 H5 0.93 . ?
C6 C7 1.446(4) . ?
C7 O2 1.289(4) . ?
C7 C8 1.428(4) . ?
C8 C9 1.347(4) . ?
C8 H8 0.93 . ?
C9 C10 1.443(4) . ?
C9 H9 0.93 . ?
C10 C11 1.390(4) . ?
C10 C15 1.405(4) . ?
C11 C12 1.379(4) . ?
C11 H11 0.93 . ?
C12 C13 1.396(4) . ?
C12 H12 0.93 . ?
C13 O3 1.358(3) . ?
C13 C14 1.383(5) . ?
C14 C15 1.374(4) . ?
C14 H14 0.93 . ?
C15 H15 0.93 . ?
C16 O3 1.424(5) . ?
C16 H16A 0.96 . ?
C16 H16B 0.96 . ?
C16 H16C 0.96 . ?
O1 B1 1.450(4) . ?
O2 B1 1.509(4) . ?
F1 B1 1.361(5) . ?
F2 B1 1.358(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 119.2(2) . . ?
O1 C1 C6 122.8(2) . . ?
C2 C1 C6 117.9(3) . . ?
C3 C2 C1 121.6(3) . . ?
C3 C2 Br1 119.3(2) . . ?
C1 C2 Br1 119.1(2) . . ?
C2 C3 C4 119.2(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 121.7(3) . . ?
C5 C4 Cl1 119.9(2) . . ?
C3 C4 Cl1 118.4(2) . . ?
C4 C5 C6 119.1(3) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 120.5(2) . . ?
C5 C6 C7 122.1(3) . . ?
C1 C6 C7 117.4(3) . . ?
O2 C7 C8 117.4(2) . . ?
O2 C7 C6 119.3(2) . . ?
C8 C7 C6 123.3(3) . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 127.9(3) . . ?
C8 C9 H9 116 . . ?
C10 C9 H9 116 . . ?
C11 C10 C15 117.8(3) . . ?
C11 C10 C9 123.6(3) . . ?
C15 C10 C9 118.6(3) . . ?
C12 C11 C10 121.8(3) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 119.0(3) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
O3 C13 C14 115.9(3) . . ?
O3 C13 C12 123.7(3) . . ?
C14 C13 C12 120.4(3) . . ?
C15 C14 C13 119.8(3) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C10 121.1(3) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 O1 B1 122.7(2) . . ?
C7 O2 B1 125.6(2) . . ?
C13 O3 C16 118.6(3) . . ?
F2 B1 F1 109.9(3) . . ?
F2 B1 O1 110.1(3) . . ?
F1 B1 O1 111.2(3) . . ?
F2 B1 O2 107.1(3) . . ?
F1 B1 O2 107.8(3) . . ?
O1 B1 O2 110.7(3) . . ?

####################################################################### 
# 
# 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_ad538
_database_code_depnum_ccdc_archive 'CCDC 1578964'
_audit_update_record             
;
2017-10-09 deposited with the CCDC.
2018-11-07 downloaded from the CCDC.
;

_audit_creation_date             2012-10-09T17:05:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H11 B1 Br1 Cl1 F2 O3'
_chemical_formula_sum            'C16 H11 B1 Br1 Cl1 F2 O3'
_chemical_formula_weight         415.42
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.5301(3)
_cell_length_b                   15.2840(7)
_cell_length_c                   13.7542(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.581(3)
_cell_angle_gamma                90
_cell_volume                     1565.25(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    16091
_cell_measurement_theta_min      3.57
_cell_measurement_theta_max      29.03
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       red
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    2.83
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.4973
_exptl_absorpt_correction_T_max  0.599

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

_diffrn_ambient_temperature      203(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_number            16091
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.57
_diffrn_reflns_theta_max         29.03
_diffrn_reflns_theta_full        29.03
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_reflns_number_total             3976
_reflns_number_gt                2632
_reflns_threshold_expression     >2σ(I)

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

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

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0322P)²+5.1255P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3976
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.105
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.1389
_refine_ls_wR_factor_gt          0.1204
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.893
_refine_diff_density_min         -1.183
_refine_diff_density_rms         0.097

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2769(6) 0.1376(3) 0.0955(3) 0.0287(8) Uani 1 1 d . . .
C2 C 0.1862(5) 0.1705(3) 0.0064(3) 0.0282(8) Uani 1 1 d . . .
C3 C 0.1802(5) 0.2585(3) -0.0133(3) 0.0294(9) Uani 1 1 d . . .
H3 H 0.1207 0.2795 -0.0728 0.035 Uiso 1 1 calc R . .
C4 C 0.2649(6) 0.3161(3) 0.0577(3) 0.0324(9) Uani 1 1 d . . .
C5 C 0.3520(6) 0.2873(3) 0.1462(3) 0.0310(9) Uani 1 1 d . . .
H5 H 0.4058 0.3271 0.1927 0.037 Uiso 1 1 calc R . .
C6 C 0.3595(5) 0.1970(3) 0.1664(3) 0.0279(8) Uani 1 1 d . . .
C7 C 0.4496(5) 0.1628(3) 0.2583(3) 0.0287(9) Uani 1 1 d . . .
C8 C 0.5281(6) 0.2168(3) 0.3373(3) 0.0315(9) Uani 1 1 d . . .
H8 H 0.5181 0.2773 0.3314 0.038 Uiso 1 1 calc R . .
C9 C 0.6174(6) 0.1815(3) 0.4210(3) 0.0327(9) Uani 1 1 d . . .
H9 H 0.6255 0.1208 0.4227 0.039 Uiso 1 1 calc R . .
C10 C 0.7013(6) 0.2270(3) 0.5077(3) 0.0304(9) Uani 1 1 d . . .
C11 C 0.7029(6) 0.3181(3) 0.5158(3) 0.0322(9) Uani 1 1 d . . .
H11 H 0.6491 0.3516 0.4631 0.039 Uiso 1 1 calc R . .
C12 C 0.7830(6) 0.3592(3) 0.6007(3) 0.0332(9) Uani 1 1 d . . .
H12 H 0.7826 0.4199 0.6053 0.04 Uiso 1 1 calc R . .
C13 C 0.8645(6) 0.3087(3) 0.6793(3) 0.0323(9) Uani 1 1 d . . .
C14 C 0.8627(6) 0.2178(3) 0.6735(3) 0.0393(11) Uani 1 1 d . . .
H14 H 0.915 0.1843 0.7266 0.047 Uiso 1 1 calc R . .
C15 C 0.7827(6) 0.1779(3) 0.5882(3) 0.0375(10) Uani 1 1 d . . .
H15 H 0.7828 0.1172 0.584 0.045 Uiso 1 1 calc R . .
C16 C 0.9415(7) 0.4353(3) 0.7784(3) 0.0480(12) Uani 1 1 d . . .
H16A H 1.0054 0.4635 0.7317 0.072 Uiso 1 1 calc R . .
H16B H 0.9962 0.4502 0.8438 0.072 Uiso 1 1 calc R . .
H16C H 0.8188 0.4545 0.7682 0.072 Uiso 1 1 calc R . .
O1 O 0.2791(5) 0.05187(19) 0.1107(2) 0.0414(8) Uani 1 1 d . . .
O2 O 0.4604(5) 0.07897(18) 0.2702(2) 0.0392(8) Uani 1 1 d . . .
O3 O 0.9478(4) 0.3426(2) 0.7656(2) 0.0403(8) Uani 1 1 d . . .
F1 F 0.5358(4) -0.0294(2) 0.1656(2) 0.0591(8) Uani 1 1 d . . .
F2 F 0.2924(4) -0.0473(2) 0.2381(2) 0.0579(8) Uani 1 1 d . . .
Cl1 Cl 0.07734(16) 0.09830(7) -0.08047(7) 0.0372(3) Uani 1 1 d . . .
Br1 Br 0.26346(9) 0.43684(3) 0.02812(4) 0.0609(2) Uani 1 1 d . . .
B1 B 0.3914(7) 0.0116(3) 0.1942(4) 0.0352(11) Uani 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.327(5) . ?
C1 C2 1.404(5) . ?
C1 C6 1.408(5) . ?
C2 C3 1.371(6) . ?
C2 Cl1 1.739(4) . ?
C3 C4 1.396(5) . ?
C3 H3 0.93 . ?
C4 C5 1.366(5) . ?
C4 Br1 1.890(4) . ?
C5 C6 1.407(5) . ?
C5 H5 0.93 . ?
C6 C7 1.441(5) . ?
C7 O2 1.293(5) . ?
C7 C8 1.420(5) . ?
C8 C9 1.356(5) . ?
C8 H8 0.93 . ?
C9 C10 1.442(5) . ?
C9 H9 0.93 . ?
C10 C11 1.397(6) . ?
C10 C15 1.400(5) . ?
C11 C12 1.384(5) . ?
C11 H11 0.93 . ?
C12 C13 1.394(5) . ?
C12 H12 0.93 . ?
C13 O3 1.359(5) . ?
C13 C14 1.391(6) . ?
C14 C15 1.378(6) . ?
C14 H14 0.93 . ?
C15 H15 0.93 . ?
C16 O3 1.431(6) . ?
C16 H16A 0.96 . ?
C16 H16B 0.96 . ?
C16 H16C 0.96 . ?
O1 B1 1.458(5) . ?
O2 B1 1.504(5) . ?
F1 B1 1.363(6) . ?
F2 B1 1.365(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 119.0(3) . . ?
O1 C1 C6 122.3(3) . . ?
C2 C1 C6 118.7(4) . . ?
C3 C2 C1 121.4(4) . . ?
C3 C2 Cl1 119.3(3) . . ?
C1 C2 Cl1 119.3(3) . . ?
C2 C3 C4 118.8(3) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 122.0(4) . . ?
C5 C4 Br1 119.5(3) . . ?
C3 C4 Br1 118.5(3) . . ?
C4 C5 C6 119.4(4) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 119.7(3) . . ?
C5 C6 C7 121.9(4) . . ?
C1 C6 C7 118.4(3) . . ?
O2 C7 C8 117.9(3) . . ?
O2 C7 C6 118.9(3) . . ?
C8 C7 C6 123.2(4) . . ?
C9 C8 C7 121.0(4) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 127.7(4) . . ?
C8 C9 H9 116.1 . . ?
C10 C9 H9 116.1 . . ?
C11 C10 C15 118.3(4) . . ?
C11 C10 C9 122.9(4) . . ?
C15 C10 C9 118.8(4) . . ?
C12 C11 C10 121.2(4) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 119.2(4) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
O3 C13 C14 115.5(4) . . ?
O3 C13 C12 123.9(4) . . ?
C14 C13 C12 120.6(4) . . ?
C15 C14 C13 119.3(4) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C10 121.4(4) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 O1 B1 122.3(3) . . ?
C7 O2 B1 125.6(3) . . ?
C13 O3 C16 117.8(3) . . ?
F1 B1 F2 109.7(4) . . ?
F1 B1 O1 111.1(4) . . ?
F2 B1 O1 109.6(4) . . ?
F1 B1 O2 107.9(4) . . ?
F2 B1 O2 107.4(4) . . ?
O1 B1 O2 111.0(3) . . ?

####################################################################### 
# 
# 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_ad173
_database_code_depnum_ccdc_archive 'CCDC 1578966'
_audit_update_record             
;
2017-10-09 deposited with the CCDC.
2018-11-07 downloaded from the CCDC.
;

_audit_creation_date             2012-02-20T15:08:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H11 B1 Br2 F2 O3'
_chemical_formula_sum            'C16 H11 B1 Br2 F2 O3'
_chemical_formula_weight         459.88
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.6071(2)
_cell_length_b                   15.4687(4)
_cell_length_c                   13.9718(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.939(1)
_cell_angle_gamma                90
_cell_volume                     1624.12(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    19090
_cell_measurement_theta_min      1.98
_cell_measurement_theta_max      28.98
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.881
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    5.024
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_absorpt_correction_T_min  0.698
_exptl_absorpt_correction_T_max  0.704

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_number            19090
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         28.98
_diffrn_reflns_theta_full        28.98
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_reflns_number_total             4211
_reflns_number_gt                2528
_reflns_threshold_expression     >2σ(I)
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

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

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

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0558P)²+2.0981P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4211
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.052
_refine_ls_wR_factor_ref         0.1481
_refine_ls_wR_factor_gt          0.1286
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.133
_refine_diff_density_min         -1.354
_refine_diff_density_rms         0.09

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.42428(8) 0.09847(3) 0.41706(3) 0.0649(2) Uani 1 1 d . . .
Br2 Br -0.24353(11) 0.43851(4) 0.53488(4) 0.0930(3) Uani 1 1 d . . .
O1 O -0.0477(5) 0.0845(2) 0.7733(2) 0.0574(8) Uani 1 1 d . . .
F2 F 0.0241(4) -0.0255(2) 0.6742(3) 0.0851(10) Uani 1 1 d . . .
O3 O 0.4375(5) 0.3361(2) 1.2657(2) 0.0621(9) Uani 1 1 d . . .
F1 F -0.2218(5) -0.0367(2) 0.7411(2) 0.0834(10) Uani 1 1 d . . .
O2 O -0.2196(5) 0.0581(2) 0.6140(2) 0.0605(9) Uani 1 1 d . . .
C12 C 0.2732(6) 0.3556(3) 1.1043(3) 0.0473(10) Uani 1 1 d . . .
H12 H 0.2733 0.4155 1.1103 0.057 Uiso 1 1 calc R . .
C2 C -0.3123(6) 0.1760(3) 0.5114(3) 0.0420(9) Uani 1 1 d . . .
C5 C -0.1556(6) 0.2904(3) 0.6518(3) 0.0460(10) Uani 1 1 d . . .
H5 H -0.1044 0.3295 0.6985 0.055 Uiso 1 1 calc R . .
C1 C -0.2254(6) 0.1421(3) 0.6002(3) 0.0422(10) Uani 1 1 d . . .
B1 B -0.1158(8) 0.0178(4) 0.6989(4) 0.0548(14) Uani 1 1 d . . .
C13 C 0.3539(6) 0.3043(3) 1.1803(3) 0.0474(10) Uani 1 1 d . . .
C6 C -0.1481(5) 0.2019(3) 0.6711(3) 0.0391(9) Uani 1 1 d . . .
C11 C 0.1926(6) 0.3166(3) 1.0195(3) 0.0483(11) Uani 1 1 d . . .
H11 H 0.1402 0.3511 0.9684 0.058 Uiso 1 1 calc R . .
C4 C -0.2389(6) 0.3193(3) 0.5637(3) 0.0480(11) Uani 1 1 d . . .
C9 C 0.1031(6) 0.1840(3) 0.9231(3) 0.0479(11) Uani 1 1 d . . .
H9 H 0.1068 0.1239 0.9248 0.057 Uiso 1 1 calc R . .
C3 C -0.3201(5) 0.2622(3) 0.4935(3) 0.0437(10) Uani 1 1 d . . .
H3 H -0.3792 0.283 0.4347 0.052 Uiso 1 1 calc R . .
C7 C -0.0583(6) 0.1672(3) 0.7620(3) 0.0439(10) Uani 1 1 d . . .
C10 C 0.1878(6) 0.2281(3) 1.0088(3) 0.0465(10) Uani 1 1 d . . .
C15 C 0.2687(7) 0.1774(3) 1.0874(3) 0.0555(12) Uani 1 1 d . . .
H15 H 0.267 0.1174 1.0821 0.067 Uiso 1 1 calc R . .
C8 C 0.0187(6) 0.2201(3) 0.8404(3) 0.0463(10) Uani 1 1 d . . .
H8 H 0.0111 0.2799 0.8349 0.056 Uiso 1 1 calc R . .
C14 C 0.3497(7) 0.2152(3) 1.1716(3) 0.0596(13) Uani 1 1 d . . .
H14 H 0.4018 0.1809 1.223 0.072 Uiso 1 1 calc R . .
C16 C 0.4313(9) 0.4262(4) 1.2822(4) 0.0769(17) Uani 1 1 d . . .
H16A H 0.4953 0.4559 1.238 0.115 Uiso 1 1 calc R . .
H16B H 0.4847 0.4387 1.3475 0.115 Uiso 1 1 calc R . .
H16C H 0.3096 0.4452 1.2721 0.115 Uiso 1 1 calc R . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C2 1.885(4) . ?
Br2 C4 1.886(4) . ?
O1 C7 1.291(5) . ?
O1 B1 1.498(6) . ?
F2 B1 1.347(7) . ?
O3 C13 1.354(5) . ?
O3 C16 1.415(7) . ?
F1 B1 1.362(7) . ?
O2 C1 1.314(5) . ?
O2 B1 1.460(6) . ?
C12 C11 1.385(6) . ?
C12 C13 1.391(6) . ?
C12 H12 0.93 . ?
C2 C3 1.357(6) . ?
C2 C1 1.413(5) . ?
C5 C4 1.369(6) . ?
C5 C6 1.395(6) . ?
C5 H5 0.93 . ?
C1 C6 1.414(5) . ?
C13 C14 1.384(7) . ?
C6 C7 1.448(5) . ?
C11 C10 1.377(6) . ?
C11 H11 0.93 . ?
C4 C3 1.392(6) . ?
C9 C8 1.351(6) . ?
C9 C10 1.440(6) . ?
C9 H9 0.93 . ?
C3 H3 0.93 . ?
C7 C8 1.419(6) . ?
C10 C15 1.411(6) . ?
C15 C14 1.371(6) . ?
C15 H15 0.93 . ?
C8 H8 0.93 . ?
C14 H14 0.93 . ?
C16 H16A 0.96 . ?
C16 H16B 0.96 . ?
C16 H16C 0.96 . ?

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
C7 O1 B1 126.1(3) . . ?
C13 O3 C16 118.5(4) . . ?
C1 O2 B1 122.9(3) . . ?
C11 C12 C13 119.3(4) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C3 C2 C1 121.9(4) . . ?
C3 C2 Br1 119.6(3) . . ?
C1 C2 Br1 118.5(3) . . ?
C4 C5 C6 119.6(4) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
O2 C1 C2 119.7(4) . . ?
O2 C1 C6 122.9(3) . . ?
C2 C1 C6 117.4(4) . . ?
F2 B1 F1 110.4(5) . . ?
F2 B1 O2 110.7(5) . . ?
F1 B1 O2 109.5(4) . . ?
F2 B1 O1 108.6(4) . . ?
F1 B1 O1 106.8(4) . . ?
O2 B1 O1 110.8(4) . . ?
O3 C13 C14 116.1(4) . . ?
O3 C13 C12 123.9(4) . . ?
C14 C13 C12 120.0(4) . . ?
C5 C6 C1 120.4(4) . . ?
C5 C6 C7 122.2(4) . . ?
C1 C6 C7 117.4(4) . . ?
C10 C11 C12 121.8(4) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C5 C4 C3 121.3(4) . . ?
C5 C4 Br2 120.1(3) . . ?
C3 C4 Br2 118.6(3) . . ?
C8 C9 C10 127.3(4) . . ?
C8 C9 H9 116.3 . . ?
C10 C9 H9 116.3 . . ?
C2 C3 C4 119.4(4) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
O1 C7 C8 117.8(4) . . ?
O1 C7 C6 119.2(4) . . ?
C8 C7 C6 123.1(4) . . ?
C11 C10 C15 117.8(4) . . ?
C11 C10 C9 124.2(4) . . ?
C15 C10 C9 117.9(4) . . ?
C14 C15 C10 121.0(5) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
C9 C8 C7 120.4(4) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C15 C14 C13 120.1(4) . . ?
C15 C14 H14 120 . . ?
C13 C14 H14 120 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

####################################################################### 
# 
# 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_ad293bf2
_database_code_depnum_ccdc_archive 'CCDC 1578967'
_audit_update_record             
;
2017-10-09 deposited with the CCDC.
2018-11-07 downloaded from the CCDC.
;

_audit_creation_date             2011-09-29T13:58:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H11 B1 F2 I2 O3'
_chemical_formula_sum            'C16 H11 B F2 I2 O3'
_chemical_formula_weight         553.86
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.0064(3)
_cell_length_b                   16.5194(5)
_cell_length_c                   15.5770(5)
_cell_angle_alpha                90
_cell_angle_beta                 123.517(2)
_cell_angle_gamma                90
_cell_volume                     1717.66(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    15471
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      28.7
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    2.142
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    3.693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.4882
_exptl_absorpt_correction_T_max  0.552

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_number            15111
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         28.7
_diffrn_reflns_theta_full        28.7
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_reflns_number_total             4285
_reflns_number_gt                2912
_reflns_threshold_expression     >2σ(I)

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

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

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0457P)²+7.5428P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4285
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.097
_refine_ls_R_factor_gt           0.0608
_refine_ls_wR_factor_ref         0.15
_refine_ls_wR_factor_gt          0.1353
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.622
_refine_diff_density_min         -1.13
_refine_diff_density_rms         0.144

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.3034(9) -0.0501(4) 1.0417(5) 0.0449(15) Uani 1 1 d . . .
C2 C 1.4409(10) -0.1063(4) 1.1164(5) 0.0474(15) Uani 1 1 d . . .
C3 C 1.6325(9) -0.0784(4) 1.1926(5) 0.0451(15) Uani 1 1 d . . .
C4 C 1.6819(10) 0.0015(4) 1.2004(5) 0.0472(15) Uani 1 1 d . . .
H4 H 1.8086 0.019 1.2527 0.057 Uiso 1 1 calc R . .
C5 C 1.5420(11) 0.0566(4) 1.1298(5) 0.0478(15) Uani 1 1 d . . .
C6 C 1.3574(10) 0.0315(4) 1.0495(5) 0.0457(15) Uani 1 1 d . . .
H6 H 1.2683 0.0685 1.0005 0.055 Uiso 1 1 calc R . .
C7 C 1.1121(10) -0.0808(5) 0.9576(5) 0.0478(16) Uani 1 1 d . . .
C8 C 0.9773(10) -0.0351(5) 0.8692(5) 0.0498(16) Uani 1 1 d . . .
H8 H 1.0144 0.0164 0.8615 0.06 Uiso 1 1 calc R . .
C9 C 0.7953(10) -0.0644(5) 0.7952(5) 0.0496(16) Uani 1 1 d . . .
H9 H 0.7675 -0.1171 0.8049 0.059 Uiso 1 1 calc R . .
C10 C 0.6418(10) -0.0248(4) 0.7050(5) 0.0459(15) Uani 1 1 d . . .
C11 C 0.6584(10) 0.0531(5) 0.6785(6) 0.0527(17) Uani 1 1 d . . .
H11 H 0.7771 0.0813 0.7213 0.063 Uiso 1 1 calc R . .
C12 C 0.5050(11) 0.0907(5) 0.5907(6) 0.0587(19) Uani 1 1 d . . .
H12 H 0.5222 0.1426 0.5736 0.07 Uiso 1 1 calc R . .
C13 C 0.3241(11) 0.0498(5) 0.5282(6) 0.0552(18) Uani 1 1 d . . .
C14 C 0.3012(11) -0.0275(5) 0.5534(6) 0.0580(19) Uani 1 1 d . . .
H14 H 0.1798 -0.0543 0.5122 0.07 Uiso 1 1 calc R . .
C15 C 0.4574(10) -0.0651(5) 0.6393(5) 0.0532(17) Uani 1 1 d . . .
H15 H 0.4415 -0.1178 0.6545 0.064 Uiso 1 1 calc R . .
C16 C 0.1817(15) 0.1624(6) 0.4134(8) 0.087(3) Uani 1 1 d . . .
H16A H 0.1977 0.1991 0.4653 0.13 Uiso 1 1 calc R . .
H16B H 0.0626 0.1761 0.3483 0.13 Uiso 1 1 calc R . .
H16C H 0.2958 0.1663 0.4085 0.13 Uiso 1 1 calc R . .
O1 O 1.0628(8) -0.1545(3) 0.9631(4) 0.0609(13) Uani 1 1 d . . .
O2 O 1.3922(8) -0.1826(3) 1.1148(4) 0.0600(14) Uani 1 1 d . . .
O3 O 0.1652(8) 0.0811(4) 0.4406(4) 0.0714(16) Uani 1 1 d . . .
F1 F 1.1020(8) -0.1813(3) 1.1186(4) 0.0805(15) Uani 1 1 d . . .
F2 F 1.1517(8) -0.2807(3) 1.0342(4) 0.0876(17) Uani 1 1 d . . .
I1 I 1.83846(7) -0.16177(3) 1.30161(4) 0.0627(2) Uani 1 1 d . . .
I2 I 1.61295(9) 0.18003(3) 1.14872(5) 0.0708(2) Uani 1 1 d . . .
B1 B 1.1817(14) -0.2017(5) 1.0618(8) 0.061(2) Uani 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.400(10) . ?
C1 C2 1.419(9) . ?
C1 C7 1.450(9) . ?
C2 O2 1.316(8) . ?
C2 C3 1.401(9) . ?
C3 C4 1.363(10) . ?
C3 I1 2.100(7) . ?
C4 C5 1.390(10) . ?
C4 H4 0.93 . ?
C5 C6 1.371(10) . ?
C5 I2 2.094(7) . ?
C6 H6 0.93 . ?
C7 O1 1.297(9) . ?
C7 C8 1.411(10) . ?
C8 C9 1.353(10) . ?
C8 H8 0.93 . ?
C9 C10 1.416(10) . ?
C9 H9 0.93 . ?
C10 C11 1.380(11) . ?
C10 C15 1.414(10) . ?
C11 C12 1.382(10) . ?
C11 H11 0.93 . ?
C12 C13 1.395(11) . ?
C12 H12 0.93 . ?
C13 O3 1.353(9) . ?
C13 C14 1.377(12) . ?
C14 C15 1.376(10) . ?
C14 H14 0.93 . ?
C15 H15 0.93 . ?
C16 O3 1.436(12) . ?
C16 H16A 0.96 . ?
C16 H16B 0.96 . ?
C16 H16C 0.96 . ?
O1 B1 1.503(11) . ?
O2 B1 1.444(11) . ?
F1 B1 1.389(12) . ?
F2 B1 1.354(10) . ?

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
C6 C1 C2 119.7(6) . . ?
C6 C1 C7 122.4(6) . . ?
C2 C1 C7 117.8(7) . . ?
O2 C2 C3 120.4(6) . . ?
O2 C2 C1 121.6(6) . . ?
C3 C2 C1 118.0(6) . . ?
C4 C3 C2 121.5(6) . . ?
C4 C3 I1 120.2(5) . . ?
C2 C3 I1 118.2(5) . . ?
C3 C4 C5 119.7(6) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 121.0(7) . . ?
C6 C5 I2 119.7(5) . . ?
C4 C5 I2 119.3(5) . . ?
C5 C6 C1 119.8(6) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
O1 C7 C8 118.0(6) . . ?
O1 C7 C1 118.4(6) . . ?
C8 C7 C1 123.5(7) . . ?
C9 C8 C7 121.5(7) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 128.0(7) . . ?
C8 C9 H9 116 . . ?
C10 C9 H9 116 . . ?
C11 C10 C15 117.2(6) . . ?
C11 C10 C9 123.6(6) . . ?
C15 C10 C9 119.2(7) . . ?
C10 C11 C12 122.4(7) . . ?
C10 C11 H11 118.8 . . ?
C12 C11 H11 118.8 . . ?
C11 C12 C13 119.1(8) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
O3 C13 C14 116.3(7) . . ?
O3 C13 C12 123.7(8) . . ?
C14 C13 C12 120.0(7) . . ?
C15 C14 C13 120.2(7) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C10 121.1(7) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C7 O1 B1 120.7(6) . . ?
C2 O2 B1 117.3(6) . . ?
C13 O3 C16 117.8(7) . . ?
F2 B1 F1 111.9(8) . . ?
F2 B1 O2 109.8(8) . . ?
F1 B1 O2 112.6(7) . . ?
F2 B1 O1 105.9(7) . . ?
F1 B1 O1 105.8(7) . . ?
O2 B1 O1 110.6(7) . . ?

####################################################################### 
# 
# 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_ad506
_database_code_depnum_ccdc_archive 'CCDC 1578965'
_audit_update_record             
;
2017-10-09 deposited with the CCDC.
2018-11-07 downloaded from the CCDC.
;

_audit_creation_date             2012-02-13T13:22:08-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H11 B1 Cl2 F2 O3'
_chemical_formula_sum            'C16 H11 B1 Cl2 F2 O3'
_chemical_formula_weight         370.96
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.5861(2)
_cell_length_b                   15.0190(4)
_cell_length_c                   13.8849(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.782(1)
_cell_angle_gamma                90
_cell_volume                     1558.98(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    17359
_cell_measurement_theta_min      2.01
_cell_measurement_theta_max      29
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.58
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.45
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.06
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_number            17359
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         29
_diffrn_reflns_theta_full        29
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_reflns_number_total             4044
_reflns_number_gt                2899
_reflns_threshold_expression     >2σ(I)

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

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

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1199P)²+1.2955P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4044
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0658
_refine_ls_wR_factor_ref         0.2363
_refine_ls_wR_factor_gt          0.2026
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.127
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.832
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.127

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2219(4) 0.14101(19) 0.4035(2) 0.0351(6) Uani 1 1 d . . .
C2 C 0.3131(4) 0.1750(2) 0.4927(2) 0.0373(6) Uani 1 1 d . . .
C3 C 0.3171(4) 0.2645(2) 0.5121(2) 0.0400(7) Uani 1 1 d . . .
H3 H 0.3767 0.2861 0.5716 0.048 Uiso 1 1 calc R . .
C4 C 0.2302(5) 0.3229(2) 0.4411(2) 0.0446(8) Uani 1 1 d . . .
C5 C 0.1431(5) 0.2933(2) 0.3526(2) 0.0406(7) Uani 1 1 d . . .
H5 H 0.0875 0.3334 0.3062 0.049 Uiso 1 1 calc R . .
C6 C 0.1384(4) 0.20167(18) 0.3325(2) 0.0326(6) Uani 1 1 d . . .
C7 C 0.0496(4) 0.16603(19) 0.2409(2) 0.0354(6) Uani 1 1 d . . .
C8 C -0.0302(4) 0.2205(2) 0.1609(2) 0.0395(7) Uani 1 1 d . . .
H8 H -0.022 0.2822 0.1662 0.047 Uiso 1 1 calc R . .
C9 C -0.1174(4) 0.1834(2) 0.0777(2) 0.0389(7) Uani 1 1 d . . .
H9 H -0.1228 0.1216 0.0763 0.047 Uiso 1 1 calc R . .
C10 C -0.2031(4) 0.2290(2) -0.0091(2) 0.0383(7) Uani 1 1 d . . .
C11 C -0.2038(4) 0.3218(2) -0.0194(2) 0.0403(7) Uani 1 1 d . . .
H11 H -0.148 0.3567 0.0323 0.048 Uiso 1 1 calc R . .
C12 C -0.2855(5) 0.3625(2) -0.1044(2) 0.0427(7) Uani 1 1 d . . .
H12 H -0.2849 0.4242 -0.1099 0.051 Uiso 1 1 calc R . .
C13 C -0.3690(4) 0.3103(2) -0.1820(2) 0.0417(7) Uani 1 1 d . . .
C14 C -0.3675(5) 0.2181(2) -0.1742(2) 0.0509(8) Uani 1 1 d . . .
H14 H -0.4213 0.1834 -0.2265 0.061 Uiso 1 1 calc R . .
C15 C -0.2867(5) 0.1784(2) -0.0893(2) 0.0483(8) Uani 1 1 d . . .
H15 H -0.2871 0.1167 -0.0845 0.058 Uiso 1 1 calc R . .
C16 C -0.4426(6) 0.4374(3) -0.2840(3) 0.0627(11) Uani 1 1 d . . .
H16A H -0.4984 0.4686 -0.2368 0.094 Uiso 1 1 calc R . .
H16B H -0.503 0.4517 -0.3486 0.094 Uiso 1 1 calc R . .
H16C H -0.3194 0.455 -0.2771 0.094 Uiso 1 1 calc R . .
B1 B 0.1109(6) 0.0125(2) 0.3050(3) 0.0449(9) Uani 1 1 d . . .
Cl1 Cl 0.42186(14) 0.10255(6) 0.57863(6) 0.0575(3) Uani 1 1 d . . .
Cl2 Cl 0.2309(2) 0.43560(6) 0.46846(8) 0.0860(5) Uani 1 1 d . . .
F1 F -0.0324(3) -0.02905(17) 0.33180(19) 0.0707(7) Uani 1 1 d . . .
F2 F 0.2087(4) -0.04720(16) 0.26353(18) 0.0704(7) Uani 1 1 d . . .
O1 O 0.0398(4) 0.08076(14) 0.22896(17) 0.0503(6) Uani 1 1 d . . .
O2 O 0.2217(4) 0.05419(14) 0.38827(18) 0.0542(7) Uani 1 1 d . . .
O3 O -0.4529(4) 0.34416(17) -0.26819(17) 0.0551(7) Uani 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.321(3) . ?
C1 C2 1.408(4) . ?
C1 C6 1.411(4) . ?
C2 C3 1.371(4) . ?
C2 Cl1 1.718(3) . ?
C3 C4 1.398(4) . ?
C3 H3 0.93 . ?
C4 C5 1.366(4) . ?
C4 Cl2 1.735(3) . ?
C5 C6 1.403(4) . ?
C5 H5 0.93 . ?
C6 C7 1.438(4) . ?
C7 O1 1.292(4) . ?
C7 C8 1.429(4) . ?
C8 C9 1.350(4) . ?
C8 H8 0.93 . ?
C9 C10 1.442(4) . ?
C9 H9 0.93 . ?
C10 C11 1.400(4) . ?
C10 C15 1.406(4) . ?
C11 C12 1.380(4) . ?
C11 H11 0.93 . ?
C12 C13 1.395(4) . ?
C12 H12 0.93 . ?
C13 O3 1.355(4) . ?
C13 C14 1.389(5) . ?
C14 C15 1.370(5) . ?
C14 H14 0.93 . ?
C15 H15 0.93 . ?
C16 O3 1.422(5) . ?
C16 H16A 0.96 . ?
C16 H16B 0.96 . ?
C16 H16C 0.96 . ?
B1 F2 1.353(4) . ?
B1 F1 1.359(5) . ?
B1 O2 1.451(4) . ?
B1 O1 1.504(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 C2 119.0(3) . . ?
O2 C1 C6 122.5(3) . . ?
C2 C1 C6 118.4(3) . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 Cl1 119.5(2) . . ?
C1 C2 Cl1 119.2(2) . . ?
C2 C3 C4 119.0(3) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 121.9(3) . . ?
C5 C4 Cl2 119.8(2) . . ?
C3 C4 Cl2 118.3(2) . . ?
C4 C5 C6 119.3(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 C7 122.2(3) . . ?
C1 C6 C7 117.7(3) . . ?
O1 C7 C8 117.4(3) . . ?
O1 C7 C6 119.4(3) . . ?
C8 C7 C6 123.2(3) . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 127.3(3) . . ?
C8 C9 H9 116.4 . . ?
C10 C9 H9 116.4 . . ?
C11 C10 C15 117.6(3) . . ?
C11 C10 C9 123.4(3) . . ?
C15 C10 C9 118.9(3) . . ?
C12 C11 C10 121.4(3) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 119.4(3) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
O3 C13 C14 116.1(3) . . ?
O3 C13 C12 123.6(3) . . ?
C14 C13 C12 120.3(3) . . ?
C15 C14 C13 119.8(3) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C10 121.5(3) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
F2 B1 F1 109.5(3) . . ?
F2 B1 O2 109.9(3) . . ?
F1 B1 O2 111.2(3) . . ?
F2 B1 O1 108.1(3) . . ?
F1 B1 O1 107.3(3) . . ?
O2 B1 O1 110.8(3) . . ?
C7 O1 B1 125.4(2) . . ?
C1 O2 B1 122.6(2) . . ?
C13 O3 C16 118.4(3) . . ?

