# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_SJ_768
_database_code_depnum_ccdc_archive 'CCDC 1526058'
_audit_update_record             
;
2017-01-07 deposited with the CCDC.
2017-07-10 downloaded from the CCDC.
;

_audit_creation_date             2017-01-02T11:17:36-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C18  H14  F3  N1  O2'
_chemical_formula_sum            'C18 H14 F3 N O2'
_chemical_formula_weight         333.3
_chemical_absolute_configuration unk

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.8605(8)
_cell_length_b                   12.7157(14)
_cell_length_c                   13.9809(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1575.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    24
_cell_measurement_theta_min      2.722
_cell_measurement_theta_max      25.114
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688

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

_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.994
_shelx_estimated_absorpt_T_max   0.998

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

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.07
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_number            12288
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.722
_diffrn_reflns_theta_max         25.114
_diffrn_reflns_theta_full        25.114
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.99
_diffrn_reflns_point_group_measured_fraction_max 0.99
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_coverage         0.726
_reflns_number_total             2788
_reflns_number_gt                2198
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0432P)²+0.0635P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2788
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.0914
_refine_ls_wR_factor_gt          0.0826
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 746 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(5)
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.047

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 0.6960(2) 0.57490(18) 0.28827(16) 0.0395(6) Uani 1 1 d . . . . .
F3 F 0.7961(2) 0.7193(2) 0.33671(16) 0.0460(7) Uani 1 1 d . . . . .
O1 O 0.3976(2) 0.55518(19) 0.18801(16) 0.0240(6) Uani 1 1 d . . . . .
F1 F 0.8601(2) 0.6534(2) 0.20056(17) 0.0475(7) Uani 1 1 d . . . . .
O2 O -0.0791(3) 0.3334(2) 0.45866(18) 0.0372(7) Uani 1 1 d . . . . .
N1 N 0.4793(3) 0.8491(2) 0.31826(19) 0.0236(7) Uani 1 1 d . . . . .
H1 H 0.544591 0.898909 0.313589 0.028 Uiso 1 1 calc R U . . .
C1 C 0.4903(4) 0.7554(3) 0.2740(2) 0.0192(8) Uani 1 1 d . . . . .
C8 C 0.3480(4) 0.8544(3) 0.3726(2) 0.0208(8) Uani 1 1 d . . . . .
C14 C 0.1317(4) 0.4421(3) 0.4581(2) 0.0230(8) Uani 1 1 d . . . . .
H14 H 0.138035 0.43223 0.523902 0.028 Uiso 1 1 calc R U . . .
C13 C 0.2337(4) 0.5072(3) 0.4118(2) 0.0225(8) Uani 1 1 d . . . . .
H13 H 0.306651 0.542541 0.447121 0.027 Uiso 1 1 calc R U . . .
C11 C 0.3368(3) 0.5890(3) 0.2624(2) 0.0188(8) Uani 1 1 d . . . . .
C2 C 0.3670(3) 0.6932(3) 0.2994(2) 0.0190(8) Uani 1 1 d . . . . .
C12 C 0.2283(3) 0.5201(3) 0.3133(2) 0.0183(8) Uani 1 1 d . . . . .
C3 C 0.2745(3) 0.7571(3) 0.3623(2) 0.0174(8) Uani 1 1 d . . . . .
C5 C 0.0772(4) 0.8272(3) 0.4605(2) 0.0271(9) Uani 1 1 d . . . . .
H5 H -0.015364 0.819471 0.491142 0.033 Uiso 1 1 calc R U . . .
C4 C 0.1335(4) 0.7452(3) 0.4081(2) 0.0229(8) Uani 1 1 d . . . . .
H4 H 0.079761 0.682636 0.40275 0.028 Uiso 1 1 calc R U . . .
C15 C 0.0199(4) 0.3919(3) 0.4055(3) 0.0238(8) Uani 1 1 d . . . . .
C16 C 0.0130(4) 0.4036(3) 0.3069(2) 0.0263(9) Uani 1 1 d . . . . .
H16 H -0.061939 0.369962 0.271837 0.032 Uiso 1 1 calc R U . . .
C9 C 0.6220(4) 0.7322(3) 0.2102(2) 0.0239(8) Uani 1 1 d . . . . .
H9A H 0.586976 0.693181 0.154853 0.029 Uiso 1 1 calc R U . . .
H9B H 0.664364 0.798043 0.187529 0.029 Uiso 1 1 calc R U . . .
C17 C 0.1191(3) 0.4659(3) 0.2615(2) 0.0224(8) Uani 1 1 d . . . . .
H17 H 0.117384 0.471599 0.195193 0.027 Uiso 1 1 calc R U . . .
C7 C 0.2923(4) 0.9374(3) 0.4246(2) 0.0265(8) Uani 1 1 d . . . . .
H7 H 0.344199 1.000663 0.429701 0.032 Uiso 1 1 calc R U . . .
C10 C 0.7430(4) 0.6704(3) 0.2592(3) 0.0321(10) Uani 1 1 d . . . . .
C6 C 0.1544(4) 0.9216(3) 0.4692(3) 0.0302(9) Uani 1 1 d . . . . .
H6 H 0.112765 0.975493 0.505682 0.036 Uiso 1 1 calc R U . . .
C18 C -0.2033(5) 0.2870(4) 0.4087(3) 0.0580(14) Uani 1 1 d . . . . .
H18A H -0.255954 0.340375 0.373422 0.087 Uiso 1 1 calc R U . . .
H18B H -0.27093 0.255143 0.453882 0.087 Uiso 1 1 calc R U . . .
H18C H -0.166443 0.234398 0.365383 0.087 Uiso 1 1 calc R U . . .



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

_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
F2 C10 1.347(4) . ?
F3 C10 1.335(4) . ?
O1 C11 1.248(4) . ?
F1 C10 1.340(4) . ?
O2 C15 1.369(4) . ?
O2 C18 1.431(4) . ?
N1 C1 1.346(4) . ?
N1 C8 1.391(4) . ?
N1 H1 0.86 . ?
C1 C2 1.395(5) . ?
C1 C9 1.499(5) . ?
C8 C7 1.373(5) . ?
C8 C3 1.407(5) . ?
C14 C13 1.385(5) . ?
C14 C15 1.390(5) . ?
C14 H14 0.93 . ?
C13 C12 1.388(5) . ?
C13 H13 0.93 . ?
C11 C2 1.447(5) . ?
C11 C12 1.481(4) . ?
C2 C3 1.451(4) . ?
C12 C17 1.392(4) . ?
C3 C4 1.412(4) . ?
C5 C4 1.370(5) . ?
C5 C6 1.387(5) . ?
C5 H5 0.93 . ?
C4 H4 0.93 . ?
C15 C16 1.387(5) . ?
C16 C17 1.384(5) . ?
C16 H16 0.93 . ?
C9 C10 1.496(5) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C17 H17 0.93 . ?
C7 C6 1.386(5) . ?
C7 H7 0.93 . ?
C6 H6 0.93 . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 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
C15 O2 C18 116.9(3) . . ?
C1 N1 C8 110.8(3) . . ?
C1 N1 H1 124.6 . . ?
C8 N1 H1 124.6 . . ?
N1 C1 C2 109.2(3) . . ?
N1 C1 C9 120.3(3) . . ?
C2 C1 C9 130.6(3) . . ?
C7 C8 N1 128.9(3) . . ?
C7 C8 C3 124.3(3) . . ?
N1 C8 C3 106.8(3) . . ?
C13 C14 C15 119.4(3) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C14 C13 C12 120.9(3) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
O1 C11 C2 122.2(3) . . ?
O1 C11 C12 118.5(3) . . ?
C2 C11 C12 119.3(3) . . ?
C1 C2 C11 125.0(3) . . ?
C1 C2 C3 106.2(3) . . ?
C11 C2 C3 128.6(3) . . ?
C13 C12 C17 118.7(3) . . ?
C13 C12 C11 121.6(3) . . ?
C17 C12 C11 119.7(3) . . ?
C8 C3 C4 117.2(3) . . ?
C8 C3 C2 107.0(3) . . ?
C4 C3 C2 135.6(3) . . ?
C4 C5 C6 121.8(3) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C4 C3 118.9(3) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
O2 C15 C16 124.7(3) . . ?
O2 C15 C14 114.8(3) . . ?
C16 C15 C14 120.5(3) . . ?
C17 C16 C15 119.2(3) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C10 C9 C1 112.9(3) . . ?
C10 C9 H9A 109 . . ?
C1 C9 H9A 109 . . ?
C10 C9 H9B 109 . . ?
C1 C9 H9B 109 . . ?
H9A C9 H9B 107.8 . . ?
C16 C17 C12 121.2(3) . . ?
C16 C17 H17 119.4 . . ?
C12 C17 H17 119.4 . . ?
C8 C7 C6 116.4(3) . . ?
C8 C7 H7 121.8 . . ?
C6 C7 H7 121.8 . . ?
F3 C10 F1 107.4(3) . . ?
F3 C10 F2 106.5(3) . . ?
F1 C10 F2 106.2(3) . . ?
F3 C10 C9 112.3(3) . . ?
F1 C10 C9 111.1(3) . . ?
F2 C10 C9 113.0(3) . . ?
C7 C6 C5 121.4(3) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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_SJ_639
_database_code_depnum_ccdc_archive 'CCDC 1526060'
_audit_update_record             
;
2017-01-07 deposited with the CCDC.
2017-07-10 downloaded from the CCDC.
;

_audit_creation_date             2016-05-02T19:14:35-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C17  H11  F3  O3'
_chemical_formula_sum            'C17 H11 F3 O3'
_chemical_formula_weight         320.26

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.159(4)
_cell_length_b                   9.480(4)
_cell_length_c                   29.456(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2836.9(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    24
_cell_measurement_theta_min      2.435
_cell_measurement_theta_max      25.856
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    1.5
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312

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

_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0992
_diffrn_reflns_av_unetI/netI     0.0666
_diffrn_reflns_number            18646
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.435
_diffrn_reflns_theta_max         25.856
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.989
_reflns_Friedel_coverage         0
_reflns_number_total             2709
_reflns_number_gt                1850
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0412P)²+3.0550P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2709
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1075
_refine_ls_R_factor_gt           0.0635
_refine_ls_wR_factor_ref         0.1409
_refine_ls_wR_factor_gt          0.1258
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.25
_refine_diff_density_rms         0.054

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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'
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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.5869(2) 0.6605(2) 0.35824(6) 0.0330(5) Uani 1 1 d . . . . .
O2 O 0.29344(19) 0.5137(2) 0.17568(6) 0.0328(5) Uani 1 1 d . . . . .
H02 H 0.2283 0.5611 0.1669 0.049 Uiso 1 1 calc R U . . .
O1 O 0.3445(2) 0.9351(2) 0.43250(6) 0.0337(5) Uani 1 1 d . . . . .
F3 F 0.5318(2) 0.8350(2) 0.50033(6) 0.0610(6) Uani 1 1 d . . . . .
F2 F 0.7328(2) 0.8645(3) 0.48207(7) 0.0669(7) Uani 1 1 d . . . . .
F1 F 0.6287(3) 0.6828(2) 0.45917(7) 0.0723(7) Uani 1 1 d . . . . .
C11 C 0.4729(3) 0.6908(3) 0.34738(9) 0.0259(7) Uani 1 1 d . . . . .
C13 C 0.3294(3) 0.7259(3) 0.27848(9) 0.0259(7) Uani 1 1 d . . . . .
H13 H 0.2956 0.8098 0.2917 0.031 Uiso 1 1 calc R U . . .
C15 C 0.3336(3) 0.5612(3) 0.21681(9) 0.0248(7) Uani 1 1 d . . . . .
C12 C 0.4201(3) 0.6453(3) 0.30257(9) 0.0245(6) Uani 1 1 d . . . . .
C6 C 0.2476(3) 0.7873(3) 0.38172(9) 0.0284(7) Uani 1 1 d . . . . .
C7 C 0.3909(3) 0.7757(3) 0.37775(9) 0.0272(7) Uani 1 1 d . . . . .
C1 C 0.2265(3) 0.8864(3) 0.41545(9) 0.0307(7) Uani 1 1 d . . . . .
C8 C 0.4411(3) 0.8651(3) 0.40968(9) 0.0285(7) Uani 1 1 d . . . . .
C17 C 0.4686(3) 0.5229(3) 0.28238(10) 0.0280(7) Uani 1 1 d . . . . .
H17 H 0.5321 0.4676 0.298 0.034 Uiso 1 1 calc R U . . .
C14 C 0.2876(3) 0.6858(3) 0.23559(9) 0.0264(7) Uani 1 1 d . . . . .
H14 H 0.2278 0.7435 0.2192 0.032 Uiso 1 1 calc R U . . .
C16 C 0.4259(3) 0.4813(3) 0.24026(10) 0.0287(7) Uani 1 1 d . . . . .
H16 H 0.4596 0.3973 0.2271 0.034 Uiso 1 1 calc R U . . .
C9 C 0.5775(3) 0.9004(3) 0.42476(9) 0.0324(7) Uani 1 1 d . . . . .
H09B H 0.5829 1.0028 0.4312 0.039 Uiso 1 1 calc R U . . .
H09A H 0.6399 0.8791 0.3999 0.039 Uiso 1 1 calc R U . . .
C5 C 0.1372(3) 0.7219(3) 0.36261(10) 0.0363(8) Uani 1 1 d . . . . .
H5 H 0.1469 0.6502 0.3403 0.044 Uiso 1 1 calc R U . . .
C4 C 0.0138(3) 0.7640(4) 0.37692(11) 0.0429(9) Uani 1 1 d . . . . .
H4 H -0.062 0.7207 0.3641 0.051 Uiso 1 1 calc R U . . .
C2 C 0.1043(3) 0.9320(3) 0.42985(10) 0.0399(8) Uani 1 1 d . . . . .
H2 H 0.0944 1.0031 0.4523 0.048 Uiso 1 1 calc R U . . .
C10 C 0.6175(3) 0.8200(4) 0.46628(11) 0.0408(8) Uani 1 1 d . . . . .
C3 C -0.0017(3) 0.8685(4) 0.40968(11) 0.0441(9) Uani 1 1 d . . . . .
H3 H -0.088 0.8964 0.4183 0.053 Uiso 1 1 calc R U . . .



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

_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
O3 C11 1.235(3) . ?
O2 C15 1.355(3) . ?
O2 H02 0.84 . ?
O1 C8 1.362(3) . ?
O1 C1 1.379(4) . ?
F3 C10 1.335(4) . ?
F2 C10 1.329(4) . ?
F1 C10 1.323(4) . ?
C11 C7 1.464(4) . ?
C11 C12 1.489(4) . ?
C13 C14 1.386(4) . ?
C13 C12 1.391(4) . ?
C13 H13 0.95 . ?
C15 C14 1.386(4) . ?
C15 C16 1.389(4) . ?
C12 C17 1.394(4) . ?
C6 C1 1.384(4) . ?
C6 C5 1.399(4) . ?
C6 C7 1.465(4) . ?
C7 C8 1.365(4) . ?
C1 C2 1.381(4) . ?
C8 C9 1.493(4) . ?
C17 C16 1.372(4) . ?
C17 H17 0.95 . ?
C14 H14 0.95 . ?
C16 H16 0.95 . ?
C9 C10 1.497(4) . ?
C9 H09B 0.99 . ?
C9 H09A 0.99 . ?
C5 C4 1.382(4) . ?
C5 H5 0.95 . ?
C4 C3 1.392(5) . ?
C4 H4 0.95 . ?
C2 C3 1.370(5) . ?
C2 H2 0.95 . ?
C3 H3 0.95 . ?

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
C15 O2 H02 109.5 . . ?
C8 O1 C1 106.5(2) . . ?
O3 C11 C7 120.2(2) . . ?
O3 C11 C12 120.0(2) . . ?
C7 C11 C12 119.7(3) . . ?
C14 C13 C12 121.2(3) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
O2 C15 C14 122.6(3) . . ?
O2 C15 C16 117.8(2) . . ?
C14 C15 C16 119.6(3) . . ?
C13 C12 C17 118.3(3) . . ?
C13 C12 C11 122.1(2) . . ?
C17 C12 C11 119.4(3) . . ?
C1 C6 C5 117.8(3) . . ?
C1 C6 C7 105.2(3) . . ?
C5 C6 C7 137.0(3) . . ?
C8 C7 C11 123.4(3) . . ?
C8 C7 C6 105.6(2) . . ?
C11 C7 C6 131.0(3) . . ?
O1 C1 C2 124.4(3) . . ?
O1 C1 C6 110.7(3) . . ?
C2 C1 C6 124.9(3) . . ?
O1 C8 C7 111.9(2) . . ?
O1 C8 C9 114.4(2) . . ?
C7 C8 C9 133.7(3) . . ?
C16 C17 C12 120.9(3) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
C15 C14 C13 119.6(3) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C17 C16 C15 120.4(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C8 C9 C10 112.4(3) . . ?
C8 C9 H09B 109.1 . . ?
C10 C9 H09B 109.1 . . ?
C8 C9 H09A 109.1 . . ?
C10 C9 H09A 109.1 . . ?
H09B C9 H09A 107.9 . . ?
C4 C5 C6 118.4(3) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C3 C2 C1 115.9(3) . . ?
C3 C2 H2 122.1 . . ?
C1 C2 H2 122.1 . . ?
F1 C10 F2 107.0(3) . . ?
F1 C10 F3 106.2(3) . . ?
F2 C10 F3 106.1(3) . . ?
F1 C10 C9 113.3(3) . . ?
F2 C10 C9 111.3(3) . . ?
F3 C10 C9 112.5(3) . . ?
C2 C3 C4 121.6(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?

####################################################################### 
# 
# 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_SJ_694
_database_code_depnum_ccdc_archive 'CCDC 1526059'
_audit_update_record             
;
2017-01-07 deposited with the CCDC.
2017-07-10 downloaded from the CCDC.
;

_audit_creation_date             2016-12-04T22:03:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C21  H13  F3  O1  S1'
_chemical_formula_sum            'C21 H13 F3 O S'
_chemical_formula_weight         370.37
_chemical_absolute_configuration unk

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   5.4622(3)
_cell_length_b                   15.8611(10)
_cell_length_c                   19.1121(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1655.81(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    139(2)
_cell_measurement_reflns_used    24
_cell_measurement_theta_min      2.488
_cell_measurement_theta_max      25.026
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760

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

_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      139(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.069
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_number            11543
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.488
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.026
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_coverage         0.695
_reflns_number_total             2917
_reflns_number_gt                2365
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0339P)²+0.1420P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2917
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.064
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.0826
_refine_ls_wR_factor_gt          0.0755
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 811 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(6)
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.048

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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'
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'
S S 0.1246 0.1234 '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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.30581(19) 0.54499(6) 0.18254(5) 0.0290(3) Uani 1 1 d . . . . .
F1 F 0.5056(5) 0.69836(16) -0.01681(10) 0.0516(8) Uani 1 1 d . . . . .
F2 F 0.3981(6) 0.57734(18) 0.02152(11) 0.0725(10) Uani 1 1 d . . . . .
F3 F 0.7640(5) 0.62025(16) 0.03685(11) 0.0527(8) Uani 1 1 d . . . . .
O1 O 0.9382(5) 0.73756(18) 0.16419(12) 0.0357(7) Uani 1 1 d . . . . .
C17 C 0.8305(8) 0.9089(3) 0.5174(2) 0.0367(11) Uani 1 1 d . . . . .
H17 H 0.854924 0.94276 0.55777 0.044 Uiso 1 1 calc R U . . .
C18 C 0.9947(8) 0.9120(2) 0.46402(19) 0.0326(10) Uani 1 1 d . . . . .
H18 H 1.132754 0.948133 0.467502 0.039 Uiso 1 1 calc R U . . .
C19 C 0.9628(7) 0.8618(2) 0.40305(19) 0.0243(9) Uani 1 1 d . . . . .
C20 C 1.1273(8) 0.8641(3) 0.3458(2) 0.0305(10) Uani 1 1 d . . . . .
H20 H 1.265895 0.900237 0.347545 0.037 Uiso 1 1 calc R U . . .
C21 C 1.0888(7) 0.8150(3) 0.28814(19) 0.0288(10) Uani 1 1 d . . . . .
H21 H 1.200004 0.817769 0.249995 0.035 Uiso 1 1 calc R U . . .
C12 C 0.8853(7) 0.7601(2) 0.28458(17) 0.0205(9) Uani 1 1 d . . . . .
C11 C 0.8439(7) 0.7125(2) 0.21793(18) 0.0233(9) Uani 1 1 d . . . . .
C2 C 0.6733(7) 0.6392(2) 0.21736(16) 0.0215(8) Uani 1 1 d . . . . .
C3 C 0.6645(7) 0.5724(2) 0.26899(16) 0.0200(8) Uani 1 1 d . . . . .
C8 C 0.4689(7) 0.5170(2) 0.25702(16) 0.0225(9) Uani 1 1 d . . . . .
C7 C 0.4248(7) 0.4478(2) 0.30015(17) 0.0281(9) Uani 1 1 d . . . . .
H7 H 0.289708 0.411355 0.291896 0.034 Uiso 1 1 calc R U . . .
C6 C 0.5830(8) 0.4336(2) 0.35516(18) 0.0305(10) Uani 1 1 d . . . . .
H6 H 0.553421 0.387878 0.386083 0.037 Uiso 1 1 calc R U . . .
C16 C 0.6261(8) 0.8563(2) 0.51309(19) 0.0309(10) Uani 1 1 d . . . . .
H16 H 0.51185 0.855044 0.550553 0.037 Uiso 1 1 calc R U . . .
C15 C 0.5883(7) 0.8066(2) 0.45576(18) 0.0254(9) Uani 1 1 d . . . . .
H15 H 0.44892 0.770792 0.453683 0.03 Uiso 1 1 calc R U . . .
C14 C 0.7563(7) 0.8082(2) 0.39948(17) 0.0216(9) Uani 1 1 d . . . . .
C13 C 0.7229(7) 0.7570(2) 0.33899(16) 0.0210(9) Uani 1 1 d . . . . .
H13 H 0.585984 0.720183 0.336429 0.025 Uiso 1 1 calc R U . . .
C5 C 0.7849(8) 0.4853(2) 0.36610(18) 0.0291(10) Uani 1 1 d . . . . .
H5 H 0.895505 0.472771 0.403037 0.035 Uiso 1 1 calc R U . . .
C4 C 0.8269(7) 0.5543(2) 0.32406(16) 0.0237(8) Uani 1 1 d . . . . .
H4 H 0.964674 0.589557 0.332235 0.028 Uiso 1 1 calc R U . . .
C1 C 0.4979(7) 0.6299(2) 0.16708(16) 0.0234(9) Uani 1 1 d . . . . .
C9 C 0.4541(8) 0.6853(2) 0.10439(16) 0.0288(10) Uani 1 1 d . . . . .
H9B H 0.277707 0.699311 0.101861 0.035 Uiso 1 1 calc R U . . .
H9A H 0.545607 0.738649 0.110504 0.035 Uiso 1 1 calc R U . . .
C10 C 0.5302(9) 0.6453(3) 0.0371(2) 0.0383(11) Uani 1 1 d . . . . .



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

_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
S1 C1 1.733(4) . ?
S1 C8 1.737(4) . ?
F1 C10 1.338(5) . ?
F2 C10 1.331(5) . ?
F3 C10 1.338(5) . ?
O1 C11 1.216(4) . ?
C17 C18 1.358(6) . ?
C17 C16 1.397(6) . ?
C17 H17 0.95 . ?
C18 C19 1.422(5) . ?
C18 H18 0.95 . ?
C19 C14 1.413(5) . ?
C19 C20 1.416(5) . ?
C20 C21 1.366(5) . ?
C20 H20 0.95 . ?
C21 C12 1.414(5) . ?
C21 H21 0.95 . ?
C12 C13 1.368(5) . ?
C12 C11 1.498(5) . ?
C11 C2 1.491(5) . ?
C2 C1 1.365(5) . ?
C2 C3 1.449(5) . ?
C3 C8 1.402(5) . ?
C3 C4 1.406(5) . ?
C8 C7 1.394(5) . ?
C7 C6 1.379(5) . ?
C7 H7 0.95 . ?
C6 C5 1.390(5) . ?
C6 H6 0.95 . ?
C16 C15 1.366(5) . ?
C16 H16 0.95 . ?
C15 C14 1.414(5) . ?
C15 H15 0.95 . ?
C14 C13 1.425(4) . ?
C13 H13 0.95 . ?
C5 C4 1.378(5) . ?
C5 H5 0.95 . ?
C4 H4 0.95 . ?
C1 C9 1.504(5) . ?
C9 C10 1.492(5) . ?
C9 H9B 0.99 . ?
C9 H9A 0.99 . ?

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 S1 C8 91.62(18) . . ?
C18 C17 C16 120.3(4) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 120.9(4) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C14 C19 C20 119.0(3) . . ?
C14 C19 C18 118.3(4) . . ?
C20 C19 C18 122.7(4) . . ?
C21 C20 C19 120.7(4) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C12 120.7(4) . . ?
C20 C21 H21 119.6 . . ?
C12 C21 H21 119.6 . . ?
C13 C12 C21 119.7(3) . . ?
C13 C12 C11 122.0(3) . . ?
C21 C12 C11 118.0(3) . . ?
O1 C11 C2 120.9(3) . . ?
O1 C11 C12 119.3(3) . . ?
C2 C11 C12 119.6(3) . . ?
C1 C2 C3 112.2(3) . . ?
C1 C2 C11 121.8(3) . . ?
C3 C2 C11 125.9(3) . . ?
C8 C3 C4 118.4(3) . . ?
C8 C3 C2 111.9(3) . . ?
C4 C3 C2 129.6(4) . . ?
C7 C8 C3 121.9(3) . . ?
C7 C8 S1 126.7(3) . . ?
C3 C8 S1 111.4(3) . . ?
C6 C7 C8 118.1(4) . . ?
C6 C7 H7 121 . . ?
C8 C7 H7 121 . . ?
C7 C6 C5 121.1(4) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C15 C16 C17 120.9(4) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C15 C14 120.1(4) . . ?
C16 C15 H15 120 . . ?
C14 C15 H15 120 . . ?
C19 C14 C15 119.5(3) . . ?
C19 C14 C13 119.0(3) . . ?
C15 C14 C13 121.5(3) . . ?
C12 C13 C14 120.9(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C4 C5 C6 120.9(4) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C4 C3 119.5(4) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C2 C1 C9 127.6(4) . . ?
C2 C1 S1 112.8(3) . . ?
C9 C1 S1 119.6(3) . . ?
C10 C9 C1 113.2(3) . . ?
C10 C9 H9B 108.9 . . ?
C1 C9 H9B 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C1 C9 H9A 108.9 . . ?
H9B C9 H9A 107.8 . . ?
F2 C10 F1 106.4(3) . . ?
F2 C10 F3 106.1(4) . . ?
F1 C10 F3 106.2(3) . . ?
F2 C10 C9 112.7(3) . . ?
F1 C10 C9 111.6(4) . . ?
F3 C10 C9 113.3(4) . . ?

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
C16 C17 C18 C19 -0.2(6) . . . . ?
C17 C18 C19 C14 -0.3(6) . . . . ?
C17 C18 C19 C20 178.9(4) . . . . ?
C14 C19 C20 C21 -0.5(6) . . . . ?
C18 C19 C20 C21 -179.7(4) . . . . ?
C19 C20 C21 C12 -0.6(6) . . . . ?
C20 C21 C12 C13 1.0(6) . . . . ?
C20 C21 C12 C11 175.8(3) . . . . ?
C13 C12 C11 O1 154.9(4) . . . . ?
C21 C12 C11 O1 -19.9(5) . . . . ?
C13 C12 C11 C2 -20.5(5) . . . . ?
C21 C12 C11 C2 164.8(3) . . . . ?
O1 C11 C2 C1 -42.9(5) . . . . ?
C12 C11 C2 C1 132.4(4) . . . . ?
O1 C11 C2 C3 139.4(4) . . . . ?
C12 C11 C2 C3 -45.3(5) . . . . ?
C1 C2 C3 C8 -3.4(4) . . . . ?
C11 C2 C3 C8 174.5(3) . . . . ?
C1 C2 C3 C4 172.7(3) . . . . ?
C11 C2 C3 C4 -9.5(6) . . . . ?
C4 C3 C8 C7 3.4(5) . . . . ?
C2 C3 C8 C7 179.9(3) . . . . ?
C4 C3 C8 S1 -174.8(3) . . . . ?
C2 C3 C8 S1 1.7(4) . . . . ?
C1 S1 C8 C7 -177.9(3) . . . . ?
C1 S1 C8 C3 0.2(3) . . . . ?
C3 C8 C7 C6 -1.2(5) . . . . ?
S1 C8 C7 C6 176.7(3) . . . . ?
C8 C7 C6 C5 -2.0(5) . . . . ?
C18 C17 C16 C15 0.5(6) . . . . ?
C17 C16 C15 C14 -0.4(6) . . . . ?
C20 C19 C14 C15 -178.8(3) . . . . ?
C18 C19 C14 C15 0.4(5) . . . . ?
C20 C19 C14 C13 1.3(5) . . . . ?
C18 C19 C14 C13 -179.5(3) . . . . ?
C16 C15 C14 C19 -0.1(5) . . . . ?
C16 C15 C14 C13 179.8(3) . . . . ?
C21 C12 C13 C14 -0.2(5) . . . . ?
C11 C12 C13 C14 -174.8(3) . . . . ?
C19 C14 C13 C12 -1.0(5) . . . . ?
C15 C14 C13 C12 179.1(3) . . . . ?
C7 C6 C5 C4 2.9(6) . . . . ?
C6 C5 C4 C3 -0.6(5) . . . . ?
C8 C3 C4 C5 -2.4(5) . . . . ?
C2 C3 C4 C5 -178.2(3) . . . . ?
C3 C2 C1 C9 -178.4(3) . . . . ?
C11 C2 C1 C9 3.6(6) . . . . ?
C3 C2 C1 S1 3.5(4) . . . . ?
C11 C2 C1 S1 -174.4(3) . . . . ?
C8 S1 C1 C2 -2.2(3) . . . . ?
C8 S1 C1 C9 179.6(3) . . . . ?
C2 C1 C9 C10 107.3(4) . . . . ?
S1 C1 C9 C10 -74.8(4) . . . . ?
C1 C9 C10 F2 64.9(5) . . . . ?
C1 C9 C10 F1 -175.4(4) . . . . ?
C1 C9 C10 F3 -55.6(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_SJ_741
_database_code_depnum_ccdc_archive 'CCDC 1526057'
_audit_update_record             
;
2017-01-07 deposited with the CCDC.
2017-07-10 downloaded from the CCDC.
;

_audit_creation_date             2016-10-27T10:19:46-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C17  H11  Br1  F3  N1  O1'
_chemical_formula_sum            'C17 H11 Br F3 N O'
_chemical_formula_weight         382.18
_chemical_absolute_configuration unk

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   8.8354(4)
_cell_length_b                   12.2152(5)
_cell_length_c                   14.1439(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1526.50(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    24
_cell_measurement_theta_min      2.718
_cell_measurement_theta_max      25.717
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760

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

_exptl_absorpt_coefficient_mu    2.728
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
        wR2(int) was 0.0758 before and 0.0460 after correction.
        The Ratio of minimum to maximum transmission is 0.9178.
        The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_correction_T_min  0.5710
_exptl_absorpt_correction_T_max  0.7453

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

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_number            12899
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.718
_diffrn_reflns_theta_max         25.717
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.984
_reflns_Friedel_coverage         0.722
_reflns_number_total             2889
_reflns_number_gt                2566
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0159P)²+0.1415P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2889
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.059
_refine_ls_wR_factor_gt          0.0566
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 960 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.020(7)
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.064

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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'
N N 0.0061 0.0033 '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'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4787(4) 0.2419(3) 0.2811(3) 0.0111(8) Uani 1 1 d . . . . .
C2 C 0.3522(4) 0.3052(3) 0.3041(3) 0.0091(8) Uani 1 1 d . . . . .
C3 C 0.2628(4) 0.2415(3) 0.3698(2) 0.0101(8) Uani 1 1 d . . . . .
C4 C 0.1219(4) 0.2524(3) 0.4142(2) 0.0123(8) Uani 1 1 d . . . . .
H4 H 0.066199 0.316569 0.407722 0.015 Uiso 1 1 calc R U . . .
C5 C 0.0668(5) 0.1669(3) 0.4675(3) 0.0147(10) Uani 1 1 d . . . . .
H5 H -0.026289 0.174627 0.497523 0.018 Uiso 1 1 calc R U . . .
C6 C 0.1468(5) 0.0688(3) 0.4778(3) 0.0165(9) Uani 1 1 d . . . . .
H6 H 0.105836 0.012396 0.513733 0.02 Uiso 1 1 calc R U . . .
C7 C 0.2851(4) 0.0550(3) 0.4354(3) 0.0144(9) Uani 1 1 d . . . . .
H7 H 0.339435 -0.009785 0.442238 0.017 Uiso 1 1 calc R U . . .
C8 C 0.3412(4) 0.1414(3) 0.3816(3) 0.0101(9) Uani 1 1 d . . . . .
C9 C 0.6105(4) 0.2665(3) 0.2180(3) 0.0145(8) Uani 1 1 d . . . . .
H9A H 0.57424 0.304087 0.162025 0.017 Uiso 1 1 calc R U . . .
H9B H 0.656168 0.198172 0.197947 0.017 Uiso 1 1 calc R U . . .
C10 C 0.7291(5) 0.3359(3) 0.2651(3) 0.0199(10) Uani 1 1 d . . . . .
C11 C 0.3184(4) 0.4110(3) 0.2623(3) 0.0120(9) Uani 1 1 d . . . . .
C12 C 0.2076(4) 0.4847(3) 0.3091(3) 0.0110(9) Uani 1 1 d . . . . .
C13 C 0.2152(5) 0.5066(3) 0.4059(3) 0.0129(9) Uani 1 1 d . . . . .
H13 H 0.287019 0.470857 0.442757 0.015 Uiso 1 1 calc R U . . .
C14 C 0.1168(4) 0.5811(3) 0.4480(3) 0.0121(8) Uani 1 1 d . . . . .
H14 H 0.122857 0.597117 0.512116 0.015 Uiso 1 1 calc R U . . .
C15 C 0.0091(5) 0.6306(3) 0.3905(3) 0.0151(10) Uani 1 1 d . . . . .
C16 C -0.0027(5) 0.6100(3) 0.2952(3) 0.0181(10) Uani 1 1 d . . . . .
H16 H -0.077371 0.643561 0.259034 0.022 Uiso 1 1 calc R U . . .
C17 C 0.0995(4) 0.5380(3) 0.2542(3) 0.0154(9) Uani 1 1 d . . . . .
H17 H 0.095775 0.525137 0.189418 0.018 Uiso 1 1 calc R U . . .
N1 N 0.4721(4) 0.1462(3) 0.3288(2) 0.0125(8) Uani 1 1 d . . . . .
H1 H 0.539764 0.095679 0.326541 0.015 Uiso 1 1 calc R U . . .
F1 F 0.8465(3) 0.3529(2) 0.20649(19) 0.0293(7) Uani 1 1 d . . . . .
F2 F 0.7846(3) 0.2878(2) 0.34283(19) 0.0266(6) Uani 1 1 d . . . . .
F3 F 0.6778(2) 0.43463(19) 0.29091(18) 0.0223(6) Uani 1 1 d . . . . .
BR1 Br -0.12868(6) 0.73242(4) 0.44573(3) 0.03101(15) Uani 1 1 d . . . . .
O1 O 0.3766(3) 0.4421(2) 0.18689(18) 0.0134(6) Uani 1 1 d . . . . .



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

_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
C1 N1 1.350(5) . ?
C1 C2 1.398(5) . ?
C1 C9 1.497(5) . ?
C2 C3 1.447(5) . ?
C2 C11 1.452(5) . ?
C3 C4 1.401(5) . ?
C3 C8 1.414(5) . ?
C4 C5 1.377(5) . ?
C4 H4 0.93 . ?
C5 C6 1.399(6) . ?
C5 H5 0.93 . ?
C6 C7 1.372(6) . ?
C6 H6 0.93 . ?
C7 C8 1.392(5) . ?
C7 H7 0.93 . ?
C8 N1 1.378(5) . ?
C9 C10 1.503(6) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 F3 1.339(5) . ?
C10 F2 1.339(5) . ?
C10 F1 1.344(5) . ?
C11 O1 1.243(5) . ?
C11 C12 1.486(5) . ?
C12 C17 1.393(5) . ?
C12 C13 1.396(5) . ?
C13 C14 1.393(5) . ?
C13 H13 0.93 . ?
C14 C15 1.389(5) . ?
C14 H14 0.93 . ?
C15 C16 1.376(6) . ?
C15 BR1 1.908(4) . ?
C16 C17 1.388(6) . ?
C16 H16 0.93 . ?
C17 H17 0.93 . ?
N1 H1 0.86 . ?

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
N1 C1 C2 109.1(3) . . ?
N1 C1 C9 120.4(3) . . ?
C2 C1 C9 130.5(3) . . ?
C1 C2 C3 106.8(3) . . ?
C1 C2 C11 124.2(4) . . ?
C3 C2 C11 128.9(3) . . ?
C4 C3 C8 117.7(3) . . ?
C4 C3 C2 136.2(4) . . ?
C8 C3 C2 105.9(3) . . ?
C5 C4 C3 119.2(4) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.8(4) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C7 C6 C5 120.7(4) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 117.5(4) . . ?
C6 C7 H7 121.2 . . ?
C8 C7 H7 121.2 . . ?
N1 C8 C7 128.8(4) . . ?
N1 C8 C3 108.1(3) . . ?
C7 C8 C3 123.1(3) . . ?
C1 C9 C10 113.1(3) . . ?
C1 C9 H9A 109 . . ?
C10 C9 H9A 109 . . ?
C1 C9 H9B 109 . . ?
C10 C9 H9B 109 . . ?
H9A C9 H9B 107.8 . . ?
F3 C10 F2 107.2(4) . . ?
F3 C10 F1 106.9(3) . . ?
F2 C10 F1 106.9(3) . . ?
F3 C10 C9 113.1(3) . . ?
F2 C10 C9 111.8(3) . . ?
F1 C10 C9 110.6(4) . . ?
O1 C11 C2 122.4(4) . . ?
O1 C11 C12 118.0(3) . . ?
C2 C11 C12 119.6(4) . . ?
C17 C12 C13 119.4(4) . . ?
C17 C12 C11 119.1(4) . . ?
C13 C12 C11 121.4(4) . . ?
C14 C13 C12 120.9(4) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C15 C14 C13 117.5(4) . . ?
C15 C14 H14 121.2 . . ?
C13 C14 H14 121.2 . . ?
C16 C15 C14 123.1(4) . . ?
C16 C15 BR1 118.2(3) . . ?
C14 C15 BR1 118.8(3) . . ?
C15 C16 C17 118.4(4) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 H16 120.8 . . ?
C16 C17 C12 120.6(4) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C1 N1 C8 110.1(3) . . ?
C1 N1 H1 124.9 . . ?
C8 N1 H1 124.9 . . ?

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
N1 C1 C2 C3 -0.6(4) . . . . ?
C9 C1 C2 C3 -178.7(4) . . . . ?
N1 C1 C2 C11 -176.9(4) . . . . ?
C9 C1 C2 C11 5.0(6) . . . . ?
C1 C2 C3 C4 -174.6(4) . . . . ?
C11 C2 C3 C4 1.4(7) . . . . ?
C1 C2 C3 C8 -0.8(4) . . . . ?
C11 C2 C3 C8 175.2(4) . . . . ?
C8 C3 C4 C5 0.6(5) . . . . ?
C2 C3 C4 C5 173.9(4) . . . . ?
C3 C4 C5 C6 -0.8(6) . . . . ?
C4 C5 C6 C7 0.7(6) . . . . ?
C5 C6 C7 C8 -0.5(6) . . . . ?
C6 C7 C8 N1 -176.6(4) . . . . ?
C6 C7 C8 C3 0.4(6) . . . . ?
C4 C3 C8 N1 177.1(3) . . . . ?
C2 C3 C8 N1 1.9(4) . . . . ?
C4 C3 C8 C7 -0.4(6) . . . . ?
C2 C3 C8 C7 -175.6(4) . . . . ?
N1 C1 C9 C10 -97.1(4) . . . . ?
C2 C1 C9 C10 80.8(5) . . . . ?
C1 C9 C10 F3 -61.9(5) . . . . ?
C1 C9 C10 F2 59.2(4) . . . . ?
C1 C9 C10 F1 178.2(3) . . . . ?
C1 C2 C11 O1 18.4(6) . . . . ?
C3 C2 C11 O1 -157.0(4) . . . . ?
C1 C2 C11 C12 -163.2(3) . . . . ?
C3 C2 C11 C12 21.4(6) . . . . ?
O1 C11 C12 C17 42.8(5) . . . . ?
C2 C11 C12 C17 -135.7(4) . . . . ?
O1 C11 C12 C13 -133.4(4) . . . . ?
C2 C11 C12 C13 48.1(5) . . . . ?
C17 C12 C13 C14 -0.3(6) . . . . ?
C11 C12 C13 C14 175.9(3) . . . . ?
C12 C13 C14 C15 1.4(6) . . . . ?
C13 C14 C15 C16 -0.7(6) . . . . ?
C13 C14 C15 BR1 179.6(3) . . . . ?
C14 C15 C16 C17 -1.2(6) . . . . ?
BR1 C15 C16 C17 178.5(3) . . . . ?
C15 C16 C17 C12 2.4(6) . . . . ?
C13 C12 C17 C16 -1.7(6) . . . . ?
C11 C12 C17 C16 -178.0(3) . . . . ?
C2 C1 N1 C8 1.9(4) . . . . ?
C9 C1 N1 C8 -179.8(3) . . . . ?
C7 C8 N1 C1 174.9(4) . . . . ?
C3 C8 N1 C1 -2.4(4) . . . . ?

