# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_191231c
_database_code_depnum_ccdc_archive 'CCDC 2044615'
loop_
_audit_author_name
_audit_author_address
'Bo Jiang'
;Jiangsu Normal University
China
;
_audit_update_record             
;
2020-11-16 deposited with the CCDC.	2021-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H10 Br Cl3 O'
_chemical_formula_weight         440.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.3649(7)
_cell_length_b                   10.1031(9)
_cell_length_c                   12.6796(11)
_cell_angle_alpha                73.1230(10)
_cell_angle_beta                 89.989(2)
_cell_angle_gamma                85.119(2)
_cell_volume                     899.26(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1371
_cell_measurement_theta_min      3.061
_cell_measurement_theta_max      25.621

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436
_exptl_absorpt_coefficient_mu    2.734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5367
_exptl_absorpt_correction_T_max  0.7350
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4575
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_sigmaI/netI    0.0749
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3115
_reflns_number_gt                1750
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0873P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3115
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0635
_refine_ls_wR_factor_ref         0.1806
_refine_ls_wR_factor_gt          0.1690
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.33271(11) -0.15485(8) 0.61423(7) 0.0861(4) Uani 1 1 d . . .
Cl1 Cl 0.6247(3) 0.8653(2) 0.95859(19) 0.0887(7) Uani 1 1 d . . .
Cl2 Cl 0.6451(3) 0.65004(19) 0.49911(13) 0.0797(6) Uani 1 1 d . . .
Cl3 Cl 0.9710(3) 0.5324(3) 0.63335(15) 0.0930(7) Uani 1 1 d . . .
O1 O 0.5677(6) 0.2149(5) 0.7238(4) 0.0707(13) Uani 1 1 d . . .
C1 C 0.7349(9) 0.5542(6) 0.6290(5) 0.0562(16) Uani 1 1 d . . .
C2 C 0.6369(9) 0.5047(6) 0.7147(5) 0.0588(16) Uani 1 1 d . . .
H2 H 0.5112 0.5240 0.7056 0.071 Uiso 1 1 calc R . .
C3 C 0.7078(8) 0.4203(6) 0.8260(5) 0.0504(15) Uani 1 1 d . . .
C4 C 0.7588(8) 0.2779(6) 0.8493(5) 0.0508(15) Uani 1 1 d . . .
C5 C 0.8318(9) 0.2002(7) 0.9535(5) 0.0592(16) Uani 1 1 d . . .
H5 H 0.8705 0.1067 0.9664 0.071 Uiso 1 1 calc R . .
C6 C 0.8463(9) 0.2615(7) 1.0365(5) 0.0617(17) Uani 1 1 d . . .
H6 H 0.8922 0.2081 1.1055 0.074 Uiso 1 1 calc R . .
C7 C 0.7930(8) 0.4033(7) 1.0192(5) 0.0531(15) Uani 1 1 d . . .
C8 C 0.7241(8) 0.4874(6) 0.9116(5) 0.0514(15) Uani 1 1 d . . .
C9 C 0.6744(8) 0.6309(6) 0.8940(5) 0.0595(17) Uani 1 1 d . . .
H9 H 0.6343 0.6869 0.8246 0.071 Uiso 1 1 calc R . .
C10 C 0.6858(8) 0.6868(7) 0.9808(6) 0.0630(18) Uani 1 1 d . . .
C11 C 0.7465(9) 0.6061(8) 1.0873(6) 0.0679(19) Uani 1 1 d . . .
H11 H 0.7492 0.6461 1.1447 0.081 Uiso 1 1 calc R . .
C12 C 0.8017(9) 0.4679(8) 1.1054(5) 0.0655(18) Uani 1 1 d . . .
H12 H 0.8456 0.4152 1.1751 0.079 Uiso 1 1 calc R . .
C13 C 0.7201(9) 0.2036(6) 0.7650(5) 0.0542(16) Uani 1 1 d . . .
C14 C 0.8718(9) 0.1129(6) 0.7332(5) 0.0532(15) Uani 1 1 d . . .
C15 C 1.0532(9) 0.1258(6) 0.7526(5) 0.0604(17) Uani 1 1 d . . .
H15 H 1.0828 0.1876 0.7906 0.073 Uiso 1 1 calc R . .
C16 C 1.1930(10) 0.0486(7) 0.7167(6) 0.0664(18) Uani 1 1 d . . .
H16 H 1.3147 0.0603 0.7280 0.080 Uiso 1 1 calc R . .
C17 C 1.1452(9) -0.0457(6) 0.6639(5) 0.0566(16) Uani 1 1 d . . .
C18 C 0.9660(11) -0.0652(7) 0.6463(5) 0.0694(19) Uani 1 1 d . . .
H18 H 0.9368 -0.1310 0.6122 0.083 Uiso 1 1 calc R . .
C19 C 0.8299(9) 0.0158(7) 0.6807(5) 0.0645(18) Uani 1 1 d . . .
H19 H 0.7084 0.0049 0.6683 0.077 Uiso 1 1 calc R . .


_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 C17 1.914(6) . ?
Cl1 C10 1.761(7) . ?
Cl2 C1 1.747(6) . ?
Cl3 C1 1.733(7) . ?
O1 C13 1.220(7) . ?
C1 C2 1.303(8) . ?
C2 C3 1.489(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.400(8) . ?
C3 C8 1.447(8) . ?
C4 C5 1.406(8) . ?
C4 C13 1.513(8) . ?
C5 C6 1.376(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.406(9) . ?
C6 H6 0.9300 . ?
C7 C12 1.431(9) . ?
C7 C8 1.448(8) . ?
C8 C9 1.416(8) . ?
C9 C10 1.381(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.410(9) . ?
C11 C12 1.373(9) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.513(9) . ?
C14 C15 1.383(9) . ?
C14 C19 1.390(8) . ?
C15 C16 1.395(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.382(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.379(9) . ?
C18 C19 1.390(9) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Cl3 122.7(5) . . ?
C2 C1 Cl2 124.3(5) . . ?
Cl3 C1 Cl2 112.9(3) . . ?
C1 C2 C3 126.0(6) . . ?
C1 C2 H2 117.0 . . ?
C3 C2 H2 117.0 . . ?
C4 C3 C8 119.5(5) . . ?
C4 C3 C2 121.4(5) . . ?
C8 C3 C2 119.0(5) . . ?
C3 C4 C5 120.9(6) . . ?
C3 C4 C13 119.7(5) . . ?
C5 C4 C13 119.1(5) . . ?
C6 C5 C4 120.5(6) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 121.3(6) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C6 C7 C12 122.1(6) . . ?
C6 C7 C8 119.6(6) . . ?
C12 C7 C8 118.4(6) . . ?
C9 C8 C3 122.6(6) . . ?
C9 C8 C7 119.3(6) . . ?
C3 C8 C7 118.1(6) . . ?
C10 C9 C8 119.5(6) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 122.3(7) . . ?
C9 C10 Cl1 119.4(6) . . ?
C11 C10 Cl1 118.4(6) . . ?
C12 C11 C10 119.3(6) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C7 121.2(7) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
O1 C13 C14 120.1(5) . . ?
O1 C13 C4 120.6(6) . . ?
C14 C13 C4 119.3(5) . . ?
C15 C14 C19 118.4(6) . . ?
C15 C14 C13 121.8(5) . . ?
C19 C14 C13 119.8(6) . . ?
C14 C15 C16 121.7(6) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C17 C16 C15 118.0(6) . . ?
C17 C16 H16 121.0 . . ?
C15 C16 H16 121.0 . . ?
C18 C17 C16 122.2(6) . . ?
C18 C17 Br1 118.4(5) . . ?
C16 C17 Br1 119.3(5) . . ?
C17 C18 C19 118.4(6) . . ?
C17 C18 H18 120.8 . . ?
C19 C18 H18 120.8 . . ?
C18 C19 C14 121.4(6) . . ?
C18 C19 H19 119.3 . . ?
C14 C19 H19 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl3 C1 C2 C3 -2.1(9) . . . . ?
Cl2 C1 C2 C3 178.7(5) . . . . ?
C1 C2 C3 C4 -80.2(8) . . . . ?
C1 C2 C3 C8 99.8(8) . . . . ?
C8 C3 C4 C5 -2.3(9) . . . . ?
C2 C3 C4 C5 177.7(6) . . . . ?
C8 C3 C4 C13 172.3(5) . . . . ?
C2 C3 C4 C13 -7.7(9) . . . . ?
C3 C4 C5 C6 3.2(9) . . . . ?
C13 C4 C5 C6 -171.5(6) . . . . ?
C4 C5 C6 C7 -1.5(10) . . . . ?
C5 C6 C7 C12 178.0(6) . . . . ?
C5 C6 C7 C8 -1.0(9) . . . . ?
C4 C3 C8 C9 -179.7(5) . . . . ?
C2 C3 C8 C9 0.3(8) . . . . ?
C4 C3 C8 C7 -0.1(8) . . . . ?
C2 C3 C8 C7 179.9(5) . . . . ?
C6 C7 C8 C9 -178.6(5) . . . . ?
C12 C7 C8 C9 2.4(8) . . . . ?
C6 C7 C8 C3 1.7(8) . . . . ?
C12 C7 C8 C3 -177.3(5) . . . . ?
C3 C8 C9 C10 177.1(6) . . . . ?
C7 C8 C9 C10 -2.5(9) . . . . ?
C8 C9 C10 C11 0.3(9) . . . . ?
C8 C9 C10 Cl1 179.7(4) . . . . ?
C9 C10 C11 C12 2.0(10) . . . . ?
Cl1 C10 C11 C12 -177.4(5) . . . . ?
C10 C11 C12 C7 -2.1(10) . . . . ?
C6 C7 C12 C11 -179.0(6) . . . . ?
C8 C7 C12 C11 -0.1(9) . . . . ?
C3 C4 C13 O1 -51.1(8) . . . . ?
C5 C4 C13 O1 123.6(7) . . . . ?
C3 C4 C13 C14 129.9(6) . . . . ?
C5 C4 C13 C14 -55.4(8) . . . . ?
O1 C13 C14 C15 161.8(6) . . . . ?
C4 C13 C14 C15 -19.1(8) . . . . ?
O1 C13 C14 C19 -16.6(9) . . . . ?
C4 C13 C14 C19 162.5(5) . . . . ?
C19 C14 C15 C16 2.8(9) . . . . ?
C13 C14 C15 C16 -175.7(6) . . . . ?
C14 C15 C16 C17 -2.2(10) . . . . ?
C15 C16 C17 C18 -0.1(10) . . . . ?
C15 C16 C17 Br1 -179.5(5) . . . . ?
C16 C17 C18 C19 1.6(10) . . . . ?
Br1 C17 C18 C19 -178.9(5) . . . . ?
C17 C18 C19 C14 -1.0(10) . . . . ?
C15 C14 C19 C18 -1.1(9) . . . . ?
C13 C14 C19 C18 177.3(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.865
_refine_diff_density_rms         0.102
####################################################################### 
# 
# 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_191231b
_database_code_depnum_ccdc_archive 'CCDC 2044618'
loop_
_audit_author_name
_audit_author_address
'Bo Jiang'
;Jiangsu Normal University
China
;
_audit_update_record             
;
2020-11-16 deposited with the CCDC.	2021-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 Br Cl F2 I O3'
_chemical_formula_weight         609.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.0114(8)
_cell_length_b                   10.0086(9)
_cell_length_c                   12.9721(11)
_cell_angle_alpha                99.895(2)
_cell_angle_beta                 92.6680(10)
_cell_angle_gamma                107.318(3)
_cell_volume                     1094.37(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2291
_cell_measurement_theta_min      3.506
_cell_measurement_theta_max      24.074

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.850
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    3.449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0080
_exptl_absorpt_correction_T_max  0.4451
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5588
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_sigmaI/netI    0.0606
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3794
_reflns_number_gt                2707
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1247P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3794
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0642
_refine_ls_wR_factor_ref         0.1958
_refine_ls_wR_factor_gt          0.1806
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.89743(12) -0.04005(13) 0.21140(8) 0.0835(4) Uani 1 1 d . . .
Cl1 Cl 0.7407(3) 0.0390(3) 0.9228(2) 0.0793(7) Uani 1 1 d . . .
F1 F 1.0123(7) 0.2990(7) 0.6413(5) 0.0906(19) Uani 1 1 d . . .
F2 F 1.0708(6) 0.5177(7) 0.6230(4) 0.0912(19) Uani 1 1 d . . .
I1 I 0.26824(6) 0.22559(7) 0.39598(4) 0.0647(3) Uani 1 1 d . . .
O1 O 0.9208(7) 0.5669(6) 0.8063(4) 0.0592(14) Uani 1 1 d . . .
O2 O 1.0569(8) 0.4220(8) 0.8364(5) 0.0752(18) Uani 1 1 d . . .
O3 O 0.3876(8) 0.5105(7) 0.8098(6) 0.0750(18) Uani 1 1 d . . .
H3 H 0.3094 0.4460 0.8159 0.112 Uiso 1 1 calc R . .
C1 C 0.9867(9) 0.4668(9) 0.7792(6) 0.0529(19) Uani 1 1 d . . .
C2 C 0.9628(9) 0.4164(10) 0.6605(6) 0.055(2) Uani 1 1 d . . .
C3 C 0.8084(9) 0.3889(8) 0.6037(6) 0.0483(17) Uani 1 1 d . . .
H3A H 0.8073 0.4142 0.5380 0.058 Uiso 1 1 calc R . .
C4 C 0.6704(7) 0.3316(7) 0.6365(5) 0.0370(14) Uani 1 1 d . . .
C5 C 0.5234(8) 0.3162(7) 0.5751(5) 0.0428(16) Uani 1 1 d . . .
C6 C 0.4133(9) 0.3788(8) 0.6383(6) 0.0517(18) Uani 1 1 d . . .
H6A H 0.3183 0.3031 0.6422 0.062 Uiso 1 1 calc R . .
H6B H 0.3853 0.4468 0.6026 0.062 Uiso 1 1 calc R . .
C7 C 0.4879(10) 0.4533(9) 0.7496(6) 0.0512(18) Uani 1 1 d . . .
H7 H 0.5791 0.5332 0.7431 0.061 Uiso 1 1 calc R . .
C8 C 0.5466(8) 0.3511(8) 0.7988(6) 0.0446(16) Uani 1 1 d . . .
C9 C 0.6437(8) 0.2894(7) 0.7396(5) 0.0413(15) Uani 1 1 d . . .
C10 C 0.7031(8) 0.1934(8) 0.7781(6) 0.0465(17) Uani 1 1 d . . .
H10 H 0.7664 0.1508 0.7387 0.056 Uiso 1 1 calc R . .
C11 C 0.6687(10) 0.1610(9) 0.8746(6) 0.0543(19) Uani 1 1 d . . .
C12 C 0.5753(10) 0.2231(10) 0.9340(7) 0.062(2) Uani 1 1 d . . .
H12 H 0.5526 0.2003 0.9992 0.074 Uiso 1 1 calc R . .
C13 C 0.5159(10) 0.3185(9) 0.8965(6) 0.058(2) Uani 1 1 d . . .
H13 H 0.4544 0.3618 0.9371 0.070 Uiso 1 1 calc R . .
C14 C 0.4900(8) 0.2495(7) 0.4750(6) 0.0452(16) Uani 1 1 d . . .
C15 C 0.5840(8) 0.1785(7) 0.4092(5) 0.0400(15) Uani 1 1 d . . .
C16 C 0.6599(9) 0.0921(8) 0.4503(6) 0.0469(17) Uani 1 1 d . . .
H16 H 0.6479 0.0782 0.5189 0.056 Uiso 1 1 calc R . .
C17 C 0.7520(10) 0.0274(8) 0.3909(7) 0.0548(19) Uani 1 1 d . . .
H17 H 0.8001 -0.0308 0.4186 0.066 Uiso 1 1 calc R . .
C18 C 0.7712(9) 0.0502(9) 0.2915(6) 0.0526(19) Uani 1 1 d . . .
C19 C 0.6999(11) 0.1325(10) 0.2480(7) 0.064(2) Uani 1 1 d . . .
H19 H 0.7137 0.1457 0.1794 0.077 Uiso 1 1 calc R . .
C20 C 0.6063(9) 0.1966(9) 0.3075(6) 0.0541(19) Uani 1 1 d . . .
H20 H 0.5575 0.2530 0.2779 0.065 Uiso 1 1 calc R . .
C21 C 0.9341(15) 0.6252(12) 0.9189(7) 0.088(3) Uani 1 1 d . . .
H21A H 0.8949 0.5486 0.9570 0.105 Uiso 1 1 calc R . .
H21B H 1.0427 0.6746 0.9450 0.105 Uiso 1 1 calc R . .
C22 C 0.8433(16) 0.7236(13) 0.9348(9) 0.107(4) Uani 1 1 d . . .
H22A H 0.8805 0.7972 0.8949 0.160 Uiso 1 1 calc R . .
H22B H 0.8542 0.7658 1.0081 0.160 Uiso 1 1 calc R . .
H22C H 0.7352 0.6730 0.9118 0.160 Uiso 1 1 calc R . .


_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 C18 1.894(8) . ?
Cl1 C11 1.732(8) . ?
F1 C2 1.365(10) . ?
F2 C2 1.356(10) . ?
I1 C14 2.131(7) . ?
O1 C1 1.317(10) . ?
O1 C21 1.462(10) . ?
O2 C1 1.180(10) . ?
O3 C7 1.405(9) . ?
O3 H3 0.8200 . ?
C1 C2 1.519(10) . ?
C2 C3 1.470(11) . ?
C3 C4 1.328(10) . ?
C3 H3A 0.9300 . ?
C4 C5 1.466(9) . ?
C4 C9 1.480(9) . ?
C5 C14 1.329(10) . ?
C5 C6 1.523(10) . ?
C6 C7 1.527(11) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.500(11) . ?
C7 H7 0.9800 . ?
C8 C13 1.382(10) . ?
C8 C9 1.399(9) . ?
C9 C10 1.380(10) . ?
C10 C11 1.373(11) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(12) . ?
C12 C13 1.369(12) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.473(10) . ?
C15 C20 1.379(10) . ?
C15 C16 1.405(10) . ?
C16 C17 1.382(11) . ?
C16 H16 0.9300 . ?
C17 C18 1.359(11) . ?
C17 H17 0.9300 . ?
C18 C19 1.360(12) . ?
C19 C20 1.390(12) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.452(16) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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
C1 O1 C21 116.1(7) . . ?
C7 O3 H3 109.5 . . ?
O2 C1 O1 126.4(7) . . ?
O2 C1 C2 123.5(8) . . ?
O1 C1 C2 110.1(7) . . ?
F2 C2 F1 104.5(7) . . ?
F2 C2 C3 109.6(7) . . ?
F1 C2 C3 111.2(7) . . ?
F2 C2 C1 104.9(6) . . ?
F1 C2 C1 105.9(7) . . ?
C3 C2 C1 119.6(6) . . ?
C4 C3 C2 126.7(7) . . ?
C4 C3 H3A 116.6 . . ?
C2 C3 H3A 116.6 . . ?
C3 C4 C5 121.8(6) . . ?
C3 C4 C9 126.1(6) . . ?
C5 C4 C9 111.8(6) . . ?
C14 C5 C4 122.3(6) . . ?
C14 C5 C6 124.3(7) . . ?
C4 C5 C6 113.4(6) . . ?
C5 C6 C7 111.7(6) . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
O3 C7 C8 113.7(6) . . ?
O3 C7 C6 112.7(7) . . ?
C8 C7 C6 108.3(6) . . ?
O3 C7 H7 107.3 . . ?
C8 C7 H7 107.3 . . ?
C6 C7 H7 107.3 . . ?
C13 C8 C9 119.4(7) . . ?
C13 C8 C7 125.4(7) . . ?
C9 C8 C7 115.2(6) . . ?
C10 C9 C8 119.5(6) . . ?
C10 C9 C4 125.0(6) . . ?
C8 C9 C4 115.4(6) . . ?
C11 C10 C9 119.9(7) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.8(7) . . ?
C10 C11 Cl1 120.2(6) . . ?
C12 C11 Cl1 119.0(6) . . ?
C13 C12 C11 119.7(7) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C8 120.6(7) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
C5 C14 C15 128.4(7) . . ?
C5 C14 I1 118.9(5) . . ?
C15 C14 I1 112.7(5) . . ?
C20 C15 C16 117.1(7) . . ?
C20 C15 C14 122.5(6) . . ?
C16 C15 C14 120.3(6) . . ?
C17 C16 C15 121.4(7) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C18 C17 C16 119.0(8) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C19 C18 C17 121.9(8) . . ?
C19 C18 Br1 119.9(6) . . ?
C17 C18 Br1 118.2(6) . . ?
C18 C19 C20 119.1(8) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C15 C20 C19 121.5(7) . . ?
C15 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C22 C21 O1 108.4(9) . . ?
C22 C21 H21A 110.0 . . ?
O1 C21 H21A 110.0 . . ?
C22 C21 H21B 110.0 . . ?
O1 C21 H21B 110.0 . . ?
H21A C21 H21B 108.4 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 O1 C1 O2 -1.4(13) . . . . ?
C21 O1 C1 C2 179.7(8) . . . . ?
O2 C1 C2 F2 -99.8(10) . . . . ?
O1 C1 C2 F2 79.1(8) . . . . ?
O2 C1 C2 F1 10.4(11) . . . . ?
O1 C1 C2 F1 -170.7(7) . . . . ?
O2 C1 C2 C3 136.8(9) . . . . ?
O1 C1 C2 C3 -44.3(10) . . . . ?
F2 C2 C3 C4 -158.5(8) . . . . ?
F1 C2 C3 C4 86.5(9) . . . . ?
C1 C2 C3 C4 -37.5(12) . . . . ?
C2 C3 C4 C5 176.7(7) . . . . ?
C2 C3 C4 C9 2.9(12) . . . . ?
C3 C4 C5 C14 54.4(10) . . . . ?
C9 C4 C5 C14 -131.0(7) . . . . ?
C3 C4 C5 C6 -127.7(7) . . . . ?
C9 C4 C5 C6 46.9(8) . . . . ?
C14 C5 C6 C7 -177.9(7) . . . . ?
C4 C5 C6 C7 4.2(9) . . . . ?
C5 C6 C7 O3 -179.3(6) . . . . ?
C5 C6 C7 C8 -52.6(8) . . . . ?
O3 C7 C8 C13 -3.5(12) . . . . ?
C6 C7 C8 C13 -129.6(8) . . . . ?
O3 C7 C8 C9 178.5(7) . . . . ?
C6 C7 C8 C9 52.4(9) . . . . ?
C13 C8 C9 C10 2.1(11) . . . . ?
C7 C8 C9 C10 -179.7(7) . . . . ?
C13 C8 C9 C4 -179.6(7) . . . . ?
C7 C8 C9 C4 -1.4(9) . . . . ?
C3 C4 C9 C10 -57.6(11) . . . . ?
C5 C4 C9 C10 128.1(7) . . . . ?
C3 C4 C9 C8 124.2(8) . . . . ?
C5 C4 C9 C8 -50.1(8) . . . . ?
C8 C9 C10 C11 -1.0(11) . . . . ?
C4 C9 C10 C11 -179.1(7) . . . . ?
C9 C10 C11 C12 0.0(12) . . . . ?
C9 C10 C11 Cl1 179.2(6) . . . . ?
C10 C11 C12 C13 0.0(13) . . . . ?
Cl1 C11 C12 C13 -179.2(7) . . . . ?
C11 C12 C13 C8 1.2(14) . . . . ?
C9 C8 C13 C12 -2.2(13) . . . . ?
C7 C8 C13 C12 179.9(8) . . . . ?
C4 C5 C14 C15 1.5(11) . . . . ?
C6 C5 C14 C15 -176.2(7) . . . . ?
C4 C5 C14 I1 177.3(5) . . . . ?
C6 C5 C14 I1 -0.4(10) . . . . ?
C5 C14 C15 C20 -135.1(8) . . . . ?
I1 C14 C15 C20 48.9(8) . . . . ?
C5 C14 C15 C16 42.6(11) . . . . ?
I1 C14 C15 C16 -133.3(6) . . . . ?
C20 C15 C16 C17 -0.4(11) . . . . ?
C14 C15 C16 C17 -178.3(7) . . . . ?
C15 C16 C17 C18 1.1(12) . . . . ?
C16 C17 C18 C19 -1.3(13) . . . . ?
C16 C17 C18 Br1 -179.8(6) . . . . ?
C17 C18 C19 C20 0.8(13) . . . . ?
Br1 C18 C19 C20 179.3(6) . . . . ?
C16 C15 C20 C19 -0.1(12) . . . . ?
C14 C15 C20 C19 177.7(7) . . . . ?
C18 C19 C20 C15 -0.1(13) . . . . ?
C1 O1 C21 C22 -174.8(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         1.223
_refine_diff_density_min         -1.971
_refine_diff_density_rms         0.189
