# Electronic Supplementary Material (ESI) for Organic 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_z
_database_code_depnum_ccdc_archive 'CCDC 1832272'
_audit_update_record             
;
2018-03-24 deposited with the CCDC.
2018-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H25 F N2 O5 S'
_chemical_formula_weight         508.55

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   13.420(2)
_cell_length_b                   5.3749(8)
_cell_length_c                   17.821(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.381(5)
_cell_angle_gamma                90.00
_cell_volume                     1239.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             532
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9334
_exptl_absorpt_correction_T_max  0.9840
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14532
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_av_sigmaI/netI    0.0771
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4154
_reflns_number_gt                2290
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0987P)²+0.1454P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(18)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4154
_refine_ls_number_parameters     325
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.1349
_refine_ls_R_factor_gt           0.0661
_refine_ls_wR_factor_ref         0.1967
_refine_ls_wR_factor_gt          0.1551
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.040
_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
S1 S 0.42560(12) 0.4336(3) 0.14491(8) 0.0676(5) Uani 1 1 d . . .
O1 O 0.3690(3) 0.5947(9) 0.1818(2) 0.0819(13) Uani 1 1 d . . .
O2 O 0.4952(3) 0.5321(8) 0.1043(2) 0.0769(13) Uani 1 1 d . . .
O3 O 0.1752(5) -0.4349(17) -0.0928(4) 0.153(3) Uani 1 1 d . . .
O4 O 0.0692(5) -0.3673(16) -0.0278(4) 0.144(3) Uani 1 1 d . . .
O5 O 0.6026(3) 0.0833(9) 0.1459(2) 0.0741(12) Uani 1 1 d . . .
F1 F 0.8168(3) 0.2829(8) 0.2859(2) 0.0980(13) Uani 1 1 d . . .
N1 N 0.4942(3) 0.2511(10) 0.2153(2) 0.0618(13) Uani 1 1 d . . .
C1 C 0.7532(4) 0.1408(12) 0.4427(3) 0.0667(17) Uani 1 1 d . . .
H1A H 0.7075 0.2637 0.4177 0.080 Uiso 1 1 calc R . .
C2 C 0.7997(5) 0.1584(16) 0.5209(3) 0.089(2) Uani 1 1 d . . .
H2A H 0.7833 0.2916 0.5487 0.107 Uiso 1 1 calc R . .
C3 C 0.8703(5) -0.0162(16) 0.5594(4) 0.082(2) Uani 1 1 d . . .
C4 C 0.8907(5) -0.2073(17) 0.5172(4) 0.090(2) Uani 1 1 d . . .
H4A H 0.9390 -0.3252 0.5419 0.109 Uiso 1 1 calc R . .
C5 C 0.8434(4) -0.2369(13) 0.4392(3) 0.0729(18) Uani 1 1 d . . .
H5A H 0.8582 -0.3754 0.4128 0.088 Uiso 1 1 calc R . .
C6 C 0.7747(4) -0.0632(13) 0.4006(3) 0.0570(13) Uani 1 1 d . . .
C7 C 0.7313(4) -0.0775(13) 0.3136(3) 0.0568(13) Uani 1 1 d . . .
C8 C 0.6700(4) -0.2940(12) 0.2765(3) 0.0706(17) Uani 1 1 d . . .
H8A H 0.6584 -0.4263 0.3103 0.085 Uiso 1 1 calc R . .
H8B H 0.6792 -0.3502 0.2271 0.085 Uiso 1 1 calc R . .
C9 C 0.6119(4) -0.0490(13) 0.2770(3) 0.0561(14) Uani 1 1 d . . .
C10 C 0.5747(4) 0.0930(12) 0.2045(3) 0.0551(14) Uani 1 1 d . . .
C11 C 0.4690(4) 0.1776(12) 0.2867(3) 0.0600(15) Uani 1 1 d . . .
C12 C 0.5372(4) -0.0061(12) 0.3229(3) 0.0605(16) Uani 1 1 d . . .
C13 C 0.5264(5) -0.1135(13) 0.3903(3) 0.0706(19) Uani 1 1 d . . .
H13A H 0.5713 -0.2381 0.4151 0.085 Uiso 1 1 calc R . .
C14 C 0.4465(6) -0.0308(19) 0.4205(4) 0.090(2) Uani 1 1 d . . .
H14A H 0.4370 -0.1032 0.4655 0.108 Uiso 1 1 calc R . .
C15 C 0.3817(5) 0.1570(19) 0.3844(4) 0.096(3) Uani 1 1 d . . .
H15A H 0.3306 0.2146 0.4065 0.115 Uiso 1 1 calc R . .
C16 C 0.3910(5) 0.2601(15) 0.3168(4) 0.082(2) Uani 1 1 d . . .
H16A H 0.3456 0.3832 0.2917 0.099 Uiso 1 1 calc R . .
C17 C 0.3411(4) 0.2241(12) 0.0851(3) 0.0588(15) Uani 1 1 d . . .
C18 C 0.3702(4) 0.0994(14) 0.0269(3) 0.0673(17) Uani 1 1 d . . .
H18A H 0.4333 0.1357 0.0171 0.081 Uiso 1 1 calc R . .
C19 C 0.3067(5) -0.0787(16) -0.0168(3) 0.0740(18) Uani 1 1 d . . .
H19A H 0.3262 -0.1649 -0.0559 0.089 Uiso 1 1 calc R . .
C20 C 0.2134(5) -0.1253(13) -0.0009(4) 0.0693(19) Uani 1 1 d . . .
C21 C 0.1817(5) 0.0001(16) 0.0553(4) 0.082(2) Uani 1 1 d . . .
H21A H 0.1175 -0.0322 0.0638 0.098 Uiso 1 1 calc R . .
C22 C 0.2463(5) 0.1745(15) 0.0990(3) 0.075(2) Uani 1 1 d . . .
H22A H 0.2265 0.2598 0.1381 0.090 Uiso 1 1 calc R . .
C23 C 0.8015(5) 0.0331(14) 0.2691(4) 0.0724(18) Uani 1 1 d . . .
H23A H 0.8674 -0.0528 0.2828 0.087 Uiso 1 1 calc R . .
H23B H 0.7710 0.0116 0.2137 0.087 Uiso 1 1 calc R . .
C24 C 0.9270(7) 0.012(3) 0.6464(5) 0.170(6) Uani 1 1 d DU . .
H24A H 0.9465 -0.1534 0.6672 0.204 Uiso 1 1 calc R . .
H24B H 0.9905 0.1030 0.6500 0.204 Uiso 1 1 calc R . .
C25 C 0.8737(11) 0.132(4) 0.6959(6) 0.267(9) Uani 1 1 d DU . .
H25A H 0.8165 0.0227 0.6969 0.321 Uiso 1 1 calc R . .
H25B H 0.8433 0.2800 0.6681 0.321 Uiso 1 1 calc R . .
C26 C 0.9202(13) 0.215(5) 0.7815(7) 0.275(10) Uani 1 1 d DU . .
H26A H 0.9625 0.3625 0.7838 0.330 Uiso 1 1 calc R . .
H26B H 0.8659 0.2500 0.8066 0.330 Uiso 1 1 calc R . .
C27 C 0.9830(14) 0.004(5) 0.8186(9) 0.305(13) Uani 1 1 d DU . .
H27A H 1.0137 0.0410 0.8725 0.457 Uiso 1 1 calc R . .
H27B H 1.0364 -0.0274 0.7930 0.457 Uiso 1 1 calc R . .
H27C H 0.9400 -0.1412 0.8147 0.457 Uiso 1 1 calc R . .
N2 N 0.1480(5) -0.3221(16) -0.0447(4) 0.098(2) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.422(5) . ?
S1 O2 1.427(4) . ?
S1 N1 1.664(5) . ?
S1 C17 1.747(6) . ?
O3 N2 1.185(8) . ?
O4 N2 1.198(7) . ?
O5 C10 1.200(6) . ?
F1 C23 1.379(8) . ?
N1 C10 1.427(7) . ?
N1 C11 1.455(7) . ?
C1 C2 1.370(7) . ?
C1 C6 1.402(8) . ?
C1 H1A 0.9300 . ?
C2 C3 1.381(10) . ?
C2 H2A 0.9300 . ?
C3 C4 1.343(10) . ?
C3 C24 1.542(9) . ?
C4 C5 1.376(9) . ?
C4 H4A 0.9300 . ?
C5 C6 1.363(8) . ?
C5 H5A 0.9300 . ?
C6 C7 1.507(7) . ?
C7 C8 1.477(8) . ?
C7 C23 1.505(9) . ?
C7 C9 1.570(7) . ?
C8 C9 1.532(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.470(7) . ?
C9 C12 1.470(7) . ?
C11 C16 1.370(8) . ?
C11 C12 1.385(8) . ?
C12 C13 1.374(8) . ?
C13 C14 1.394(9) . ?
C13 H13A 0.9300 . ?
C14 C15 1.376(11) . ?
C14 H14A 0.9300 . ?
C15 C16 1.362(9) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 C18 1.375(8) . ?
C17 C22 1.384(7) . ?
C18 C19 1.378(9) . ?
C18 H18A 0.9300 . ?
C19 C20 1.378(8) . ?
C19 H19A 0.9300 . ?
C20 C21 1.367(9) . ?
C20 N2 1.460(9) . ?
C21 C22 1.371(9) . ?
C21 H21A 0.9300 . ?
C22 H22A 0.9300 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.428(9) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.553(9) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.463(10) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 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
O1 S1 O2 120.7(3) . . ?
O1 S1 N1 105.5(2) . . ?
O2 S1 N1 107.2(2) . . ?
O1 S1 C17 109.6(3) . . ?
O2 S1 C17 109.7(3) . . ?
N1 S1 C17 102.7(3) . . ?
C10 N1 C11 108.5(5) . . ?
C10 N1 S1 122.4(4) . . ?
C11 N1 S1 127.5(4) . . ?
C2 C1 C6 119.6(6) . . ?
C2 C1 H1A 120.2 . . ?
C6 C1 H1A 120.2 . . ?
C1 C2 C3 121.8(7) . . ?
C1 C2 H2A 119.1 . . ?
C3 C2 H2A 119.1 . . ?
C4 C3 C2 117.1(6) . . ?
C4 C3 C24 121.2(8) . . ?
C2 C3 C24 121.7(9) . . ?
C3 C4 C5 123.1(7) . . ?
C3 C4 H4A 118.4 . . ?
C5 C4 H4A 118.4 . . ?
C6 C5 C4 120.0(7) . . ?
C6 C5 H5A 120.0 . . ?
C4 C5 H5A 120.0 . . ?
C5 C6 C1 118.3(5) . . ?
C5 C6 C7 120.6(6) . . ?
C1 C6 C7 120.8(5) . . ?
C8 C7 C23 115.3(5) . . ?
C8 C7 C6 121.2(5) . . ?
C23 C7 C6 113.4(5) . . ?
C8 C7 C9 60.3(4) . . ?
C23 C7 C9 117.1(5) . . ?
C6 C7 C9 119.7(4) . . ?
C7 C8 C9 62.9(4) . . ?
C7 C8 H8A 117.5 . . ?
C9 C8 H8A 117.5 . . ?
C7 C8 H8B 117.5 . . ?
C9 C8 H8B 117.5 . . ?
H8A C8 H8B 114.5 . . ?
C10 C9 C12 106.6(5) . . ?
C10 C9 C8 119.7(5) . . ?
C12 C9 C8 124.1(5) . . ?
C10 C9 C7 119.1(5) . . ?
C12 C9 C7 123.8(4) . . ?
C8 C9 C7 56.9(4) . . ?
O5 C10 N1 124.5(5) . . ?
O5 C10 C9 129.1(6) . . ?
N1 C10 C9 106.4(4) . . ?
C16 C11 C12 121.8(6) . . ?
C16 C11 N1 129.3(6) . . ?
C12 C11 N1 108.8(5) . . ?
C13 C12 C11 119.8(6) . . ?
C13 C12 C9 131.7(6) . . ?
C11 C12 C9 108.5(5) . . ?
C12 C13 C14 118.3(7) . . ?
C12 C13 H13A 120.9 . . ?
C14 C13 H13A 120.9 . . ?
C15 C14 C13 120.6(7) . . ?
C15 C14 H14A 119.7 . . ?
C13 C14 H14A 119.7 . . ?
C16 C15 C14 121.1(7) . . ?
C16 C15 H15A 119.4 . . ?
C14 C15 H15A 119.4 . . ?
C15 C16 C11 118.3(7) . . ?
C15 C16 H16A 120.8 . . ?
C11 C16 H16A 120.8 . . ?
C18 C17 C22 119.9(6) . . ?
C18 C17 S1 120.4(5) . . ?
C22 C17 S1 119.6(5) . . ?
C17 C18 C19 120.6(6) . . ?
C17 C18 H18A 119.7 . . ?
C19 C18 H18A 119.7 . . ?
C18 C19 C20 118.0(6) . . ?
C18 C19 H19A 121.0 . . ?
C20 C19 H19A 121.0 . . ?
C21 C20 C19 122.5(6) . . ?
C21 C20 N2 119.3(6) . . ?
C19 C20 N2 118.2(6) . . ?
C20 C21 C22 118.7(6) . . ?
C20 C21 H21A 120.6 . . ?
C22 C21 H21A 120.6 . . ?
C21 C22 C17 120.2(6) . . ?
C21 C22 H22A 119.9 . . ?
C17 C22 H22A 119.9 . . ?
F1 C23 C7 110.3(5) . . ?
F1 C23 H23A 109.6 . . ?
C7 C23 H23A 109.6 . . ?
F1 C23 H23B 109.6 . . ?
C7 C23 H23B 109.6 . . ?
H23A C23 H23B 108.1 . . ?
C25 C24 C3 118.0(8) . . ?
C25 C24 H24A 107.8 . . ?
C3 C24 H24A 107.8 . . ?
C25 C24 H24B 107.8 . . ?
C3 C24 H24B 107.8 . . ?
H24A C24 H24B 107.1 . . ?
C24 C25 C26 126.9(12) . . ?
C24 C25 H25A 105.6 . . ?
C26 C25 H25A 105.6 . . ?
C24 C25 H25B 105.6 . . ?
C26 C25 H25B 105.6 . . ?
H25A C25 H25B 106.1 . . ?
C27 C26 C25 104.7(13) . . ?
C27 C26 H26A 110.8 . . ?
C25 C26 H26A 110.8 . . ?
C27 C26 H26B 110.8 . . ?
C25 C26 H26B 110.8 . . ?
H26A C26 H26B 108.9 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O3 N2 O4 122.7(8) . . ?
O3 N2 C20 120.0(6) . . ?
O4 N2 C20 117.3(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 N1 C10 -168.7(4) . . . . ?
O2 S1 N1 C10 -39.0(5) . . . . ?
C17 S1 N1 C10 76.5(5) . . . . ?
O1 S1 N1 C11 27.6(5) . . . . ?
O2 S1 N1 C11 157.4(5) . . . . ?
C17 S1 N1 C11 -87.1(5) . . . . ?
C6 C1 C2 C3 2.0(10) . . . . ?
C1 C2 C3 C4 -0.9(11) . . . . ?
C1 C2 C3 C24 176.6(8) . . . . ?
C2 C3 C4 C5 -1.2(12) . . . . ?
C24 C3 C4 C5 -178.7(8) . . . . ?
C3 C4 C5 C6 2.2(11) . . . . ?
C4 C5 C6 C1 -1.0(9) . . . . ?
C4 C5 C6 C7 173.1(6) . . . . ?
C2 C1 C6 C5 -1.0(9) . . . . ?
C2 C1 C6 C7 -175.1(6) . . . . ?
C5 C6 C7 C8 61.1(7) . . . . ?
C1 C6 C7 C8 -124.9(6) . . . . ?
C5 C6 C7 C23 -82.8(7) . . . . ?
C1 C6 C7 C23 91.2(7) . . . . ?
C5 C6 C7 C9 132.3(6) . . . . ?
C1 C6 C7 C9 -53.7(8) . . . . ?
C23 C7 C8 C9 -108.0(5) . . . . ?
C6 C7 C8 C9 108.7(6) . . . . ?
C7 C8 C9 C10 107.3(6) . . . . ?
C7 C8 C9 C12 -111.1(5) . . . . ?
C8 C7 C9 C10 -108.3(6) . . . . ?
C23 C7 C9 C10 -3.2(8) . . . . ?
C6 C7 C9 C10 140.5(6) . . . . ?
C8 C7 C9 C12 111.7(7) . . . . ?
C23 C7 C9 C12 -143.2(6) . . . . ?
C6 C7 C9 C12 0.5(10) . . . . ?
C23 C7 C9 C8 105.1(6) . . . . ?
C6 C7 C9 C8 -111.2(7) . . . . ?
C11 N1 C10 O5 169.1(6) . . . . ?
S1 N1 C10 O5 2.8(8) . . . . ?
C11 N1 C10 C9 -10.0(6) . . . . ?
S1 N1 C10 C9 -176.4(4) . . . . ?
C12 C9 C10 O5 -167.8(6) . . . . ?
C8 C9 C10 O5 -20.2(9) . . . . ?
C7 C9 C10 O5 46.1(9) . . . . ?
C12 C9 C10 N1 11.3(6) . . . . ?
C8 C9 C10 N1 158.9(5) . . . . ?
C7 C9 C10 N1 -134.8(5) . . . . ?
C10 N1 C11 C16 -173.5(6) . . . . ?
S1 N1 C11 C16 -8.0(9) . . . . ?
C10 N1 C11 C12 4.9(6) . . . . ?
S1 N1 C11 C12 170.4(4) . . . . ?
C16 C11 C12 C13 1.1(9) . . . . ?
N1 C11 C12 C13 -177.4(5) . . . . ?
C16 C11 C12 C9 -179.1(6) . . . . ?
N1 C11 C12 C9 2.4(6) . . . . ?
C10 C9 C12 C13 171.2(6) . . . . ?
C8 C9 C12 C13 25.5(9) . . . . ?
C7 C9 C12 C13 -44.6(10) . . . . ?
C10 C9 C12 C11 -8.5(6) . . . . ?
C8 C9 C12 C11 -154.3(5) . . . . ?
C7 C9 C12 C11 135.6(6) . . . . ?
C11 C12 C13 C14 -0.5(9) . . . . ?
C9 C12 C13 C14 179.7(6) . . . . ?
C12 C13 C14 C15 -1.3(11) . . . . ?
C13 C14 C15 C16 2.6(12) . . . . ?
C14 C15 C16 C11 -2.1(12) . . . . ?
C12 C11 C16 C15 0.2(10) . . . . ?
N1 C11 C16 C15 178.4(6) . . . . ?
O1 S1 C17 C18 161.1(5) . . . . ?
O2 S1 C17 C18 26.5(6) . . . . ?
N1 S1 C17 C18 -87.2(5) . . . . ?
O1 S1 C17 C22 -22.2(6) . . . . ?
O2 S1 C17 C22 -156.7(5) . . . . ?
N1 S1 C17 C22 89.6(5) . . . . ?
C22 C17 C18 C19 -1.3(9) . . . . ?
S1 C17 C18 C19 175.4(5) . . . . ?
C17 C18 C19 C20 0.6(10) . . . . ?
C18 C19 C20 C21 0.9(10) . . . . ?
C18 C19 C20 N2 -177.2(6) . . . . ?
C19 C20 C21 C22 -1.7(11) . . . . ?
N2 C20 C21 C22 176.3(6) . . . . ?
C20 C21 C22 C17 1.0(11) . . . . ?
C18 C17 C22 C21 0.5(9) . . . . ?
S1 C17 C22 C21 -176.3(5) . . . . ?
C8 C7 C23 F1 152.1(5) . . . . ?
C6 C7 C23 F1 -61.8(7) . . . . ?
C9 C7 C23 F1 84.1(7) . . . . ?
C4 C3 C24 C25 -150.5(13) . . . . ?
C2 C3 C24 C25 32.1(18) . . . . ?
C3 C24 C25 C26 -170.2(19) . . . . ?
C24 C25 C26 C27 -45(3) . . . . ?
C21 C20 N2 O3 -178.9(8) . . . . ?
C19 C20 N2 O3 -0.8(11) . . . . ?
C21 C20 N2 O4 -1.2(10) . . . . ?
C19 C20 N2 O4 176.9(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_z_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1832274'
_audit_update_record             
;
2018-03-24 deposited with the CCDC.
2018-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 Br F O2'
_chemical_formula_weight         363.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   6.6841(6)
_cell_length_b                   8.7074(8)
_cell_length_c                   14.4482(13)
_cell_angle_alpha                87.391(3)
_cell_angle_beta                 81.591(2)
_cell_angle_gamma                78.532(3)
_cell_volume                     815.14(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    2.535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5070
_exptl_absorpt_correction_T_max  0.7507
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9422
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0609
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.42
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4504
_reflns_number_gt                4096
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1042P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.041(15)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4504
_refine_ls_number_parameters     398
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1463
_refine_ls_wR_factor_gt          0.1409
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
Br2 Br 0.86797(8) 0.60035(7) 0.46495(5) 0.0381(2) Uani 1 1 d . . .
O3 O -0.1148(9) 0.7000(8) 0.8701(5) 0.0561(17) Uani 1 1 d . . .
O4 O 0.2241(9) 0.5992(6) 0.8523(3) 0.0352(12) Uani 1 1 d . . .
F2 F -0.1350(8) 1.1884(5) 0.8997(3) 0.0440(11) Uani 1 1 d . . .
C19 C 0.2710(12) 0.7549(9) 0.5971(5) 0.0307(16) Uani 1 1 d . . .
H19A H 0.1387 0.7751 0.5807 0.037 Uiso 1 1 calc R . .
C20 C 0.4418(12) 0.7052(8) 0.5303(5) 0.0290(15) Uani 1 1 d . . .
H20A H 0.4261 0.6936 0.4683 0.035 Uiso 1 1 calc R . .
C21 C 0.6358(13) 0.6734(9) 0.5585(5) 0.0292(18) Uani 1 1 d . . .
C22 C 0.6670(12) 0.6880(8) 0.6483(5) 0.0290(15) Uani 1 1 d . . .
H22A H 0.7992 0.6648 0.6648 0.035 Uiso 1 1 calc R . .
C23 C 0.4971(11) 0.7382(8) 0.7147(5) 0.0239(16) Uani 1 1 d . . .
H23A H 0.5154 0.7476 0.7766 0.029 Uiso 1 1 calc R . .
C24 C 0.3019(11) 0.7742(8) 0.6900(5) 0.0248(16) Uani 1 1 d . . .
C25 C 0.1124(10) 0.8266(8) 0.7622(4) 0.0254(14) Uani 1 1 d . . .
C26 C -0.0695(10) 0.9384(8) 0.7355(5) 0.0276(14) Uani 1 1 d . . .
H26A H -0.0649 0.9722 0.6705 0.033 Uiso 1 1 calc R . .
H26B H -0.2046 0.9255 0.7660 0.033 Uiso 1 1 calc R . .
C27 C 0.0635(10) 0.9997(8) 0.7923(5) 0.0263(14) Uani 1 1 d . . .
C29 C 0.3762(11) 1.1208(9) 0.7804(5) 0.0277(15) Uani 1 1 d . . .
H29A H 0.4196 1.0535 0.8286 0.033 Uiso 1 1 calc R . .
C30 C 0.4969(13) 1.2281(9) 0.7429(6) 0.0356(18) Uani 1 1 d . . .
H30A H 0.6186 1.2313 0.7661 0.043 Uiso 1 1 calc R . .
C31 C 0.4378(16) 1.3280(11) 0.6724(7) 0.041(2) Uani 1 1 d . . .
H31A H 0.5169 1.4007 0.6476 0.049 Uiso 1 1 calc R . .
C32 C 0.2504(15) 1.3189(11) 0.6369(7) 0.045(2) Uani 1 1 d . . .
H32A H 0.2080 1.3851 0.5882 0.054 Uiso 1 1 calc R . .
C33 C 0.1337(13) 1.2119(9) 0.6752(5) 0.0326(18) Uani 1 1 d . . .
H33A H 0.0126 1.2066 0.6520 0.039 Uiso 1 1 calc R . .
C34 C -0.0232(15) 1.0365(11) 0.8939(6) 0.035(2) Uani 1 1 d . . .
H34A H -0.1115 0.9638 0.9184 0.042 Uiso 1 1 calc R . .
H34B H 0.0886 1.0248 0.9312 0.042 Uiso 1 1 calc R . .
C35 C 0.0591(12) 0.7051(9) 0.8335(5) 0.0301(16) Uani 1 1 d . . .
C36 C 0.1781(16) 0.4694(9) 0.9136(5) 0.047(2) Uani 1 1 d . . .
H36A H 0.3044 0.3999 0.9231 0.070 Uiso 1 1 calc R . .
H36B H 0.0933 0.4135 0.8853 0.070 Uiso 1 1 calc R . .
H36C H 0.1064 0.5094 0.9727 0.070 Uiso 1 1 calc R . .
C38 C 0.1946(13) 1.1112(9) 0.7485(5) 0.0294(18) Uani 1 1 d . . .
Br1 Br -0.26891(9) 1.09606(7) 0.49926(5) 0.0412(2) Uani 1 1 d . . .
F1 F 0.7554(7) 0.6752(7) 0.1124(4) 0.0567(14) Uani 1 1 d . . .
O1 O 0.4673(10) 0.9784(7) 0.0039(3) 0.0462(14) Uani 1 1 d . . .
O2 O 0.4625(9) 1.0662(6) 0.1469(3) 0.0292(11) Uani 1 1 d . . .
C1 C -0.0541(11) 0.9512(9) 0.2278(5) 0.0316(16) Uani 1 1 d . . .
H1A H -0.1130 0.9416 0.1743 0.038 Uiso 1 1 calc R . .
C2 C -0.1778(12) 1.0078(9) 0.3087(5) 0.0333(16) Uani 1 1 d . . .
H2A H -0.3194 1.0377 0.3089 0.040 Uiso 1 1 calc R . .
C3 C -0.0970(12) 1.0207(9) 0.3874(5) 0.0289(17) Uani 1 1 d . . .
C4 C 0.1185(11) 0.9765(9) 0.3895(5) 0.0274(15) Uani 1 1 d . . .
H4A H 0.1753 0.9849 0.4436 0.033 Uiso 1 1 calc R . .
C5 C 0.2398(12) 0.9208(9) 0.3081(6) 0.0318(18) Uani 1 1 d . . .
H5A H 0.3814 0.8904 0.3081 0.038 Uiso 1 1 calc R . .
C6 C 0.1590(11) 0.9080(8) 0.2258(5) 0.0214(14) Uani 1 1 d . . .
C7 C 0.2956(10) 0.8549(8) 0.1354(4) 0.0254(14) Uani 1 1 d . . .
C8 C 0.2203(11) 0.7546(8) 0.0719(5) 0.0294(15) Uani 1 1 d . . .
H8A H 0.0861 0.7280 0.0914 0.035 Uiso 1 1 calc R . .
H8B H 0.2532 0.7713 0.0050 0.035 Uiso 1 1 calc R . .
C9 C 0.3914(11) 0.6793(8) 0.1236(5) 0.0275(15) Uani 1 1 d . . .
C10 C 0.3599(12) 0.5690(9) 0.2062(5) 0.0246(16) Uani 1 1 d . . .
C11 C 0.1908(12) 0.4894(9) 0.2137(5) 0.0277(16) Uani 1 1 d . . .
H11A H 0.0954 0.5100 0.1717 0.033 Uiso 1 1 calc R . .
C12 C 0.1740(14) 0.3795(10) 0.2864(7) 0.036(2) Uani 1 1 d . . .
H12A H 0.0643 0.3270 0.2929 0.043 Uiso 1 1 calc R . .
C13 C 0.3116(15) 0.3471(10) 0.3473(5) 0.041(2) Uani 1 1 d . . .
H13A H 0.2979 0.2716 0.3942 0.049 Uiso 1 1 calc R . .
C14 C 0.4724(13) 0.4257(9) 0.3402(5) 0.0366(17) Uani 1 1 d . . .
H14A H 0.5661 0.4049 0.3830 0.044 Uiso 1 1 calc R . .
C15 C 0.4946(13) 0.5363(9) 0.2690(5) 0.0334(17) Uani 1 1 d . . .
H15A H 0.6041 0.5888 0.2645 0.040 Uiso 1 1 calc R . .
C16 C 0.5995(12) 0.6396(10) 0.0639(6) 0.0303(18) Uani 1 1 d . . .
H16A H 0.6302 0.5290 0.0492 0.036 Uiso 1 1 calc R . .
H16B H 0.5971 0.6992 0.0056 0.036 Uiso 1 1 calc R . .
C17 C 0.4136(11) 0.9713(8) 0.0867(5) 0.0293(15) Uani 1 1 d . . .
C18 C 0.5677(14) 1.1884(9) 0.1046(6) 0.0402(19) Uani 1 1 d . . .
H18A H 0.5952 1.2503 0.1528 0.060 Uiso 1 1 calc R . .
H18B H 0.4819 1.2542 0.0648 0.060 Uiso 1 1 calc R . .
H18C H 0.6952 1.1414 0.0681 0.060 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
Br2 C21 1.926(7) . ?
O3 C35 1.213(9) . ?
O4 C35 1.342(10) . ?
O4 C36 1.457(9) . ?
F2 C34 1.383(11) . ?
C19 C20 1.393(10) . ?
C19 C24 1.410(10) . ?
C19 H19A 0.9300 . ?
C20 C21 1.388(12) . ?
C20 H20A 0.9300 . ?
C21 C22 1.359(11) . ?
C22 C23 1.387(10) . ?
C22 H22A 0.9300 . ?
C23 C24 1.375(11) . ?
C23 H23A 0.9300 . ?
C24 C25 1.526(10) . ?
C25 C26 1.486(10) . ?
C25 C35 1.500(10) . ?
C25 C27 1.546(10) . ?
C26 C27 1.480(10) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C38 1.494(9) . ?
C27 C34 1.521(11) . ?
C29 C38 1.379(11) . ?
C29 C30 1.394(10) . ?
C29 H29A 0.9300 . ?
C30 C31 1.360(13) . ?
C30 H30A 0.9300 . ?
C31 C32 1.439(15) . ?
C31 H31A 0.9300 . ?
C32 C33 1.377(12) . ?
C32 H32A 0.9300 . ?
C33 C38 1.399(11) . ?
C33 H33A 0.9300 . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
Br1 C3 1.902(8) . ?
F1 C16 1.427(9) . ?
O1 C17 1.200(8) . ?
O2 C17 1.343(9) . ?
O2 C18 1.453(9) . ?
C1 C2 1.379(10) . ?
C1 C6 1.395(10) . ?
C1 H1A 0.9300 . ?
C2 C3 1.347(11) . ?
C2 H2A 0.9300 . ?
C3 C4 1.419(11) . ?
C4 C5 1.375(11) . ?
C4 H4A 0.9300 . ?
C5 C6 1.395(11) . ?
C5 H5A 0.9300 . ?
C6 C7 1.514(9) . ?
C7 C17 1.496(9) . ?
C7 C8 1.497(10) . ?
C7 C9 1.543(10) . ?
C8 C9 1.484(10) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C16 1.510(11) . ?
C9 C10 1.515(10) . ?
C10 C15 1.352(11) . ?
C10 C11 1.428(11) . ?
C11 C12 1.395(12) . ?
C11 H11A 0.9300 . ?
C12 C13 1.346(13) . ?
C12 H12A 0.9300 . ?
C13 C14 1.374(12) . ?
C13 H13A 0.9300 . ?
C14 C15 1.389(11) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C35 O4 C36 115.1(6) . . ?
C20 C19 C24 118.9(7) . . ?
C20 C19 H19A 120.5 . . ?
C24 C19 H19A 120.5 . . ?
C21 C20 C19 118.5(7) . . ?
C21 C20 H20A 120.8 . . ?
C19 C20 H20A 120.8 . . ?
C22 C21 C20 123.0(7) . . ?
C22 C21 Br2 119.5(6) . . ?
C20 C21 Br2 117.4(6) . . ?
C21 C22 C23 118.5(8) . . ?
C21 C22 H22A 120.7 . . ?
C23 C22 H22A 120.7 . . ?
C24 C23 C22 120.7(7) . . ?
C24 C23 H23A 119.7 . . ?
C22 C23 H23A 119.7 . . ?
C23 C24 C19 120.3(7) . . ?
C23 C24 C25 121.6(6) . . ?
C19 C24 C25 118.0(7) . . ?
C26 C25 C35 114.0(6) . . ?
C26 C25 C24 120.5(6) . . ?
C35 C25 C24 116.0(6) . . ?
C26 C25 C27 58.4(5) . . ?
C35 C25 C27 118.1(6) . . ?
C24 C25 C27 117.7(5) . . ?
C27 C26 C25 62.8(4) . . ?
C27 C26 H26A 117.5 . . ?
C25 C26 H26A 117.5 . . ?
C27 C26 H26B 117.5 . . ?
C25 C26 H26B 117.5 . . ?
H26A C26 H26B 114.6 . . ?
C26 C27 C38 119.4(6) . . ?
C26 C27 C34 117.1(6) . . ?
C38 C27 C34 112.9(6) . . ?
C26 C27 C25 58.8(4) . . ?
C38 C27 C25 120.2(6) . . ?
C34 C27 C25 118.3(6) . . ?
C38 C29 C30 122.1(7) . . ?
C38 C29 H29A 119.0 . . ?
C30 C29 H29A 119.0 . . ?
C31 C30 C29 120.4(8) . . ?
C31 C30 H30A 119.8 . . ?
C29 C30 H30A 119.8 . . ?
C30 C31 C32 118.6(8) . . ?
C30 C31 H31A 120.7 . . ?
C32 C31 H31A 120.7 . . ?
C33 C32 C31 119.9(8) . . ?
C33 C32 H32A 120.0 . . ?
C31 C32 H32A 120.0 . . ?
C32 C33 C38 120.9(8) . . ?
C32 C33 H33A 119.5 . . ?
C38 C33 H33A 119.5 . . ?
F2 C34 C27 109.4(7) . . ?
F2 C34 H34A 109.8 . . ?
C27 C34 H34A 109.8 . . ?
F2 C34 H34B 109.8 . . ?
C27 C34 H34B 109.8 . . ?
H34A C34 H34B 108.2 . . ?
O3 C35 O4 122.6(7) . . ?
O3 C35 C25 124.2(8) . . ?
O4 C35 C25 113.1(6) . . ?
O4 C36 H36A 109.5 . . ?
O4 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
O4 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C29 C38 C33 118.1(7) . . ?
C29 C38 C27 121.2(7) . . ?
C33 C38 C27 120.8(7) . . ?
C17 O2 C18 115.5(6) . . ?
C2 C1 C6 120.2(7) . . ?
C2 C1 H1A 119.9 . . ?
C6 C1 H1A 119.9 . . ?
C3 C2 C1 121.1(7) . . ?
C3 C2 H2A 119.4 . . ?
C1 C2 H2A 119.4 . . ?
C2 C3 C4 120.9(7) . . ?
C2 C3 Br1 120.9(6) . . ?
C4 C3 Br1 118.2(6) . . ?
C5 C4 C3 117.3(7) . . ?
C5 C4 H4A 121.4 . . ?
C3 C4 H4A 121.4 . . ?
C4 C5 C6 122.6(7) . . ?
C4 C5 H5A 118.7 . . ?
C6 C5 H5A 118.7 . . ?
C5 C6 C1 117.9(7) . . ?
C5 C6 C7 121.9(6) . . ?
C1 C6 C7 120.1(6) . . ?
C17 C7 C8 114.9(6) . . ?
C17 C7 C6 116.0(6) . . ?
C8 C7 C6 118.3(6) . . ?
C17 C7 C9 117.9(6) . . ?
C8 C7 C9 58.4(5) . . ?
C6 C7 C9 118.9(5) . . ?
C9 C8 C7 62.3(5) . . ?
C9 C8 H8A 117.5 . . ?
C7 C8 H8A 117.5 . . ?
C9 C8 H8B 117.5 . . ?
C7 C8 H8B 117.5 . . ?
H8A C8 H8B 114.6 . . ?
C8 C9 C16 114.7(6) . . ?
C8 C9 C10 122.2(6) . . ?
C16 C9 C10 114.6(7) . . ?
C8 C9 C7 59.2(5) . . ?
C16 C9 C7 116.7(6) . . ?
C10 C9 C7 118.4(6) . . ?
C15 C10 C11 119.4(7) . . ?
C15 C10 C9 121.9(7) . . ?
C11 C10 C9 118.6(7) . . ?
C12 C11 C10 117.6(7) . . ?
C12 C11 H11A 121.2 . . ?
C10 C11 H11A 121.2 . . ?
C13 C12 C11 122.1(8) . . ?
C13 C12 H12A 119.0 . . ?
C11 C12 H12A 119.0 . . ?
C12 C13 C14 120.0(7) . . ?
C12 C13 H13A 120.0 . . ?
C14 C13 H13A 120.0 . . ?
C13 C14 C15 119.8(8) . . ?
C13 C14 H14A 120.1 . . ?
C15 C14 H14A 120.1 . . ?
C10 C15 C14 121.2(8) . . ?
C10 C15 H15A 119.4 . . ?
C14 C15 H15A 119.4 . . ?
F1 C16 C9 110.1(6) . . ?
F1 C16 H16A 109.6 . . ?
C9 C16 H16A 109.6 . . ?
F1 C16 H16B 109.6 . . ?
C9 C16 H16B 109.6 . . ?
H16A C16 H16B 108.2 . . ?
O1 C17 O2 122.4(6) . . ?
O1 C17 C7 125.3(7) . . ?
O2 C17 C7 112.2(6) . . ?
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 . . ?

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
C24 C19 C20 C21 1.3(10) . . . . ?
C19 C20 C21 C22 0.2(11) . . . . ?
C19 C20 C21 Br2 178.6(5) . . . . ?
C20 C21 C22 C23 -0.5(11) . . . . ?
Br2 C21 C22 C23 -178.9(5) . . . . ?
C21 C22 C23 C24 -0.8(10) . . . . ?
C22 C23 C24 C19 2.4(11) . . . . ?
C22 C23 C24 C25 178.8(6) . . . . ?
C20 C19 C24 C23 -2.6(10) . . . . ?
C20 C19 C24 C25 -179.2(6) . . . . ?
C23 C24 C25 C26 148.1(7) . . . . ?
C19 C24 C25 C26 -35.4(9) . . . . ?
C23 C24 C25 C35 -67.6(9) . . . . ?
C19 C24 C25 C35 108.9(8) . . . . ?
C23 C24 C25 C27 80.3(9) . . . . ?
C19 C24 C25 C27 -103.2(8) . . . . ?
C35 C25 C26 C27 109.3(6) . . . . ?
C24 C25 C26 C27 -105.7(7) . . . . ?
C25 C26 C27 C38 109.5(7) . . . . ?
C25 C26 C27 C34 -108.3(7) . . . . ?
C35 C25 C27 C26 -102.3(7) . . . . ?
C24 C25 C27 C26 110.5(7) . . . . ?
C26 C25 C27 C38 -108.1(7) . . . . ?
C35 C25 C27 C38 149.6(7) . . . . ?
C24 C25 C27 C38 2.3(10) . . . . ?
C26 C25 C27 C34 106.1(7) . . . . ?
C35 C25 C27 C34 3.8(10) . . . . ?
C24 C25 C27 C34 -143.4(7) . . . . ?
C38 C29 C30 C31 0.0(12) . . . . ?
C29 C30 C31 C32 -0.8(13) . . . . ?
C30 C31 C32 C33 0.9(14) . . . . ?
C31 C32 C33 C38 0.0(14) . . . . ?
C26 C27 C34 F2 -87.5(8) . . . . ?
C38 C27 C34 F2 57.0(9) . . . . ?
C25 C27 C34 F2 -154.8(6) . . . . ?
C36 O4 C35 O3 5.2(11) . . . . ?
C36 O4 C35 C25 -173.8(6) . . . . ?
C26 C25 C35 O3 -3.0(10) . . . . ?
C24 C25 C35 O3 -149.6(8) . . . . ?
C27 C25 C35 O3 62.6(10) . . . . ?
C26 C25 C35 O4 176.0(6) . . . . ?
C24 C25 C35 O4 29.4(9) . . . . ?
C27 C25 C35 O4 -118.4(7) . . . . ?
C30 C29 C38 C33 0.9(11) . . . . ?
C30 C29 C38 C27 -177.6(7) . . . . ?
C32 C33 C38 C29 -0.9(12) . . . . ?
C32 C33 C38 C27 177.6(8) . . . . ?
C26 C27 C38 C29 -152.3(7) . . . . ?
C34 C27 C38 C29 64.0(10) . . . . ?
C25 C27 C38 C29 -83.5(9) . . . . ?
C26 C27 C38 C33 29.3(10) . . . . ?
C34 C27 C38 C33 -114.4(8) . . . . ?
C25 C27 C38 C33 98.1(9) . . . . ?
C6 C1 C2 C3 -1.0(11) . . . . ?
C1 C2 C3 C4 0.2(11) . . . . ?
C1 C2 C3 Br1 -179.1(5) . . . . ?
C2 C3 C4 C5 0.1(11) . . . . ?
Br1 C3 C4 C5 179.3(5) . . . . ?
C3 C4 C5 C6 0.5(11) . . . . ?
C4 C5 C6 C1 -1.3(10) . . . . ?
C4 C5 C6 C7 176.6(6) . . . . ?
C2 C1 C6 C5 1.5(10) . . . . ?
C2 C1 C6 C7 -176.4(6) . . . . ?
C5 C6 C7 C17 -73.8(8) . . . . ?
C1 C6 C7 C17 104.0(7) . . . . ?
C5 C6 C7 C8 143.6(7) . . . . ?
C1 C6 C7 C8 -38.6(9) . . . . ?
C5 C6 C7 C9 76.0(8) . . . . ?
C1 C6 C7 C9 -106.2(8) . . . . ?
C17 C7 C8 C9 108.7(6) . . . . ?
C6 C7 C8 C9 -108.3(6) . . . . ?
C7 C8 C9 C16 -107.6(6) . . . . ?
C7 C8 C9 C10 106.2(7) . . . . ?
C17 C7 C9 C8 -103.5(7) . . . . ?
C6 C7 C9 C8 107.3(7) . . . . ?
C17 C7 C9 C16 0.6(10) . . . . ?
C8 C7 C9 C16 104.1(7) . . . . ?
C6 C7 C9 C16 -148.6(7) . . . . ?
C17 C7 C9 C10 143.9(7) . . . . ?
C8 C7 C9 C10 -112.5(7) . . . . ?
C6 C7 C9 C10 -5.3(10) . . . . ?
C8 C9 C10 C15 -160.6(7) . . . . ?
C16 C9 C10 C15 53.2(10) . . . . ?
C7 C9 C10 C15 -90.9(9) . . . . ?
C8 C9 C10 C11 23.9(10) . . . . ?
C16 C9 C10 C11 -122.3(8) . . . . ?
C7 C9 C10 C11 93.6(8) . . . . ?
C15 C10 C11 C12 -0.4(11) . . . . ?
C9 C10 C11 C12 175.2(7) . . . . ?
C10 C11 C12 C13 -0.6(12) . . . . ?
C11 C12 C13 C14 1.4(13) . . . . ?
C12 C13 C14 C15 -1.2(13) . . . . ?
C11 C10 C15 C14 0.6(12) . . . . ?
C9 C10 C15 C14 -174.9(7) . . . . ?
C13 C14 C15 C10 0.2(13) . . . . ?
C8 C9 C16 F1 139.0(7) . . . . ?
C10 C9 C16 F1 -72.2(8) . . . . ?
C7 C9 C16 F1 72.5(9) . . . . ?
C18 O2 C17 O1 5.8(11) . . . . ?
C18 O2 C17 C7 -176.8(6) . . . . ?
C8 C7 C17 O1 -7.7(11) . . . . ?
C6 C7 C17 O1 -151.7(7) . . . . ?
C9 C7 C17 O1 58.2(10) . . . . ?
C8 C7 C17 O2 174.9(6) . . . . ?
C6 C7 C17 O2 31.0(9) . . . . ?
C9 C7 C17 O2 -119.1(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.594
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.151
