# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_z
_database_code_depnum_ccdc_archive 'CCDC 1525745'
_audit_update_record             
;
2017-01-05 deposited with the CCDC.
2017-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H25 F3 N O S'
_chemical_formula_weight         456.53

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2

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

_cell_length_a                   23.660(2)
_cell_length_b                   10.2673(10)
_cell_length_c                   10.5398(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2560.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6558
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      22.15

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             956
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9282
_exptl_absorpt_correction_T_max  0.9554
_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  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29756
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4527
_reflns_number_gt                3353
_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)+(0.0969P)²+0.9324P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.16(19)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4527
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0617
_refine_ls_wR_factor_ref         0.1950
_refine_ls_wR_factor_gt          0.1818
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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 0.36410(7) 0.97072(17) 0.21401(14) 0.1053(5) Uani 1 1 d . . .
O1 O 0.57674(10) 0.4757(3) 0.6423(3) 0.0602(7) Uani 1 1 d . . .
H1C H 0.556(2) 0.512(5) 0.570(4) 0.086(14) Uiso 1 1 d . . .
F1 F 0.60501(14) 0.9472(3) 0.7790(4) 0.1103(10) Uani 1 1 d . . .
F2 F 0.64675(13) 0.8318(4) 0.9152(3) 0.1133(11) Uani 1 1 d . . .
F3 F 0.56224(16) 0.9003(4) 0.9487(4) 0.1298(14) Uani 1 1 d . . .
N1 N 0.58234(13) 0.7389(3) 0.5711(3) 0.0571(8) Uani 1 1 d . . .
H1B H 0.5967 0.7415 0.4962 0.069 Uiso 1 1 calc R . .
C1 C 0.50238(19) 0.8168(4) 0.3731(4) 0.0683(11) Uani 1 1 d . . .
H1A H 0.5363 0.7824 0.3437 0.082 Uiso 1 1 calc R . .
C2 C 0.4627(2) 0.8638(5) 0.2880(5) 0.0778(12) Uani 1 1 d . . .
H2A H 0.4706 0.8624 0.2017 0.093 Uiso 1 1 calc R . .
C3 C 0.41129(18) 0.9129(4) 0.3293(4) 0.0670(11) Uani 1 1 d . . .
C4 C 0.39979(17) 0.9139(4) 0.4559(4) 0.0671(11) Uani 1 1 d . . .
H4A H 0.3651 0.9445 0.4848 0.080 Uiso 1 1 calc R . .
C5 C 0.43946(17) 0.8698(4) 0.5411(4) 0.0603(10) Uani 1 1 d . . .
H5A H 0.4309 0.8730 0.6272 0.072 Uiso 1 1 calc R . .
C6 C 0.49101(15) 0.8213(4) 0.5051(4) 0.0575(9) Uani 1 1 d . . .
C7 C 0.53232(15) 0.7750(3) 0.5975(4) 0.0528(9) Uani 1 1 d . . .
C8 C 0.51790(17) 0.7634(5) 0.7355(4) 0.0729(12) Uani 1 1 d . . .
H8A H 0.4898 0.6960 0.7488 0.088 Uiso 1 1 calc R . .
H8B H 0.5033 0.8452 0.7678 0.088 Uiso 1 1 calc R . .
C9 C 0.57241(17) 0.7285(4) 0.8002(4) 0.0664(10) Uani 1 1 d . . .
C10 C 0.61224(15) 0.6929(4) 0.6828(4) 0.0610(10) Uani 1 1 d . . .
H10A H 0.6474 0.7428 0.6908 0.073 Uiso 1 1 calc R . .
C11 C 0.62797(15) 0.5465(4) 0.6625(4) 0.0612(10) Uani 1 1 d . . .
C12 C 0.65742(16) 0.4849(4) 0.7769(4) 0.0665(10) Uani 1 1 d . . .
C13 C 0.70103(18) 0.5499(5) 0.8389(5) 0.0754(12) Uani 1 1 d . . .
H13A H 0.7127 0.6317 0.8115 0.090 Uiso 1 1 calc R . .
C14 C 0.7269(2) 0.4910(6) 0.9423(5) 0.0964(16) Uani 1 1 d . . .
H14A H 0.7559 0.5340 0.9846 0.116 Uiso 1 1 calc R . .
C15 C 0.7102(3) 0.3704(7) 0.9827(7) 0.1056(19) Uani 1 1 d . . .
H15A H 0.7272 0.3336 1.0537 0.127 Uiso 1 1 calc R . .
C16 C 0.6699(3) 0.3050(6) 0.9218(6) 0.1057(19) Uani 1 1 d . . .
H16A H 0.6593 0.2223 0.9490 0.127 Uiso 1 1 calc R . .
C17 C 0.64328(19) 0.3625(5) 0.8154(5) 0.0821(14) Uani 1 1 d . . .
H17A H 0.6158 0.3161 0.7712 0.098 Uiso 1 1 calc R . .
C18 C 0.66743(15) 0.5285(4) 0.5495(4) 0.0588(9) Uani 1 1 d . . .
C19 C 0.67083(19) 0.4054(4) 0.4930(5) 0.0783(13) Uani 1 1 d . . .
H19A H 0.6480 0.3381 0.5225 0.094 Uiso 1 1 calc R . .
C20 C 0.7075(2) 0.3830(6) 0.3946(6) 0.0945(17) Uani 1 1 d . . .
H20A H 0.7088 0.3010 0.3572 0.113 Uiso 1 1 calc R . .
C21 C 0.7422(2) 0.4796(6) 0.3506(5) 0.0855(13) Uani 1 1 d . . .
H21A H 0.7668 0.4628 0.2837 0.103 Uiso 1 1 calc R . .
C22 C 0.7409(2) 0.5991(5) 0.4039(5) 0.0849(14) Uani 1 1 d . . .
H22A H 0.7652 0.6636 0.3746 0.102 Uiso 1 1 calc R . .
C23 C 0.70321(16) 0.6270(4) 0.5032(5) 0.0691(11) Uani 1 1 d . . .
H23A H 0.7019 0.7101 0.5381 0.083 Uiso 1 1 calc R . .
C24 C 0.5978(2) 0.8518(6) 0.8581(6) 0.0897(15) Uani 1 1 d . . .
C25 C 0.3236(2) 1.0902(5) 0.2991(6) 0.1008(17) Uani 1 1 d . . .
H25A H 0.2960 1.1278 0.2434 0.151 Uiso 1 1 calc R . .
H25B H 0.3484 1.1573 0.3298 0.151 Uiso 1 1 calc R . .
H25C H 0.3049 1.0495 0.3694 0.151 Uiso 1 1 calc R . .
C26 C 0.5643(2) 0.6275(6) 0.9018(6) 0.1039(17) Uani 1 1 d . . .
H26A H 0.5390 0.6605 0.9653 0.156 Uiso 1 1 calc R . .
H26B H 0.6001 0.6075 0.9400 0.156 Uiso 1 1 calc R . .
H26C H 0.5486 0.5500 0.8649 0.156 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
S1 C3 1.754(4) . ?
S1 C25 1.796(6) . ?
O1 C11 1.429(4) . ?
O1 H1C 0.98(5) . ?
F1 C24 1.298(7) . ?
F2 C24 1.321(6) . ?
F3 C24 1.366(6) . ?
N1 C7 1.271(5) . ?
N1 C10 1.452(5) . ?
N1 H1B 0.8600 . ?
C1 C2 1.385(6) . ?
C1 C6 1.418(6) . ?
C1 H1A 0.9300 . ?
C2 C3 1.386(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.362(6) . ?
C4 C5 1.376(6) . ?
C4 H4A 0.9300 . ?
C5 C6 1.371(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.460(5) . ?
C7 C8 1.498(6) . ?
C8 C9 1.502(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C26 1.503(7) . ?
C9 C24 1.528(7) . ?
C9 C10 1.598(6) . ?
C10 C11 1.563(5) . ?
C10 H10A 0.9800 . ?
C11 C18 1.524(6) . ?
C11 C12 1.530(5) . ?
C12 C17 1.363(6) . ?
C12 C13 1.392(6) . ?
C13 C14 1.389(7) . ?
C13 H13A 0.9300 . ?
C14 C15 1.367(8) . ?
C14 H14A 0.9300 . ?
C15 C16 1.331(8) . ?
C15 H15A 0.9300 . ?
C16 C17 1.415(7) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 C19 1.400(6) . ?
C18 C23 1.406(6) . ?
C19 C20 1.372(8) . ?
C19 H19A 0.9300 . ?
C20 C21 1.368(8) . ?
C20 H20A 0.9300 . ?
C21 C22 1.350(7) . ?
C21 H21A 0.9300 . ?
C22 C23 1.405(7) . ?
C22 H22A 0.9300 . ?
C23 H23A 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 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
C3 S1 C25 103.0(3) . . ?
C11 O1 H1C 110(3) . . ?
C7 N1 C10 111.8(3) . . ?
C7 N1 H1B 124.1 . . ?
C10 N1 H1B 124.1 . . ?
C2 C1 C6 119.6(4) . . ?
C2 C1 H1A 120.2 . . ?
C6 C1 H1A 120.2 . . ?
C1 C2 C3 121.3(4) . . ?
C1 C2 H2A 119.4 . . ?
C3 C2 H2A 119.4 . . ?
C4 C3 C2 119.0(4) . . ?
C4 C3 S1 123.3(3) . . ?
C2 C3 S1 117.7(4) . . ?
C3 C4 C5 120.0(4) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C6 C5 C4 123.1(4) . . ?
C6 C5 H5A 118.5 . . ?
C4 C5 H5A 118.5 . . ?
C5 C6 C1 116.9(4) . . ?
C5 C6 C7 121.9(4) . . ?
C1 C6 C7 121.2(3) . . ?
N1 C7 C6 124.9(4) . . ?
N1 C7 C8 113.7(4) . . ?
C6 C7 C8 121.4(3) . . ?
C7 C8 C9 105.3(3) . . ?
C7 C8 H8A 110.7 . . ?
C9 C8 H8A 110.7 . . ?
C7 C8 H8B 110.7 . . ?
C9 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?
C8 C9 C26 112.2(4) . . ?
C8 C9 C24 108.7(4) . . ?
C26 C9 C24 109.7(4) . . ?
C8 C9 C10 102.1(3) . . ?
C26 C9 C10 118.0(4) . . ?
C24 C9 C10 105.5(4) . . ?
N1 C10 C11 108.5(3) . . ?
N1 C10 C9 105.4(3) . . ?
C11 C10 C9 117.8(3) . . ?
N1 C10 H10A 108.2 . . ?
C11 C10 H10A 108.2 . . ?
C9 C10 H10A 108.2 . . ?
O1 C11 C18 110.0(3) . . ?
O1 C11 C12 107.0(3) . . ?
C18 C11 C12 106.6(3) . . ?
O1 C11 C10 107.9(3) . . ?
C18 C11 C10 111.7(3) . . ?
C12 C11 C10 113.4(3) . . ?
C17 C12 C13 119.0(4) . . ?
C17 C12 C11 120.3(4) . . ?
C13 C12 C11 120.6(4) . . ?
C14 C13 C12 119.1(5) . . ?
C14 C13 H13A 120.4 . . ?
C12 C13 H13A 120.4 . . ?
C15 C14 C13 120.7(5) . . ?
C15 C14 H14A 119.7 . . ?
C13 C14 H14A 119.7 . . ?
C16 C15 C14 121.0(6) . . ?
C16 C15 H15A 119.5 . . ?
C14 C15 H15A 119.5 . . ?
C15 C16 C17 119.4(6) . . ?
C15 C16 H16A 120.3 . . ?
C17 C16 H16A 120.3 . . ?
C12 C17 C16 120.7(5) . . ?
C12 C17 H17A 119.6 . . ?
C16 C17 H17A 119.6 . . ?
C19 C18 C23 117.8(4) . . ?
C19 C18 C11 118.5(4) . . ?
C23 C18 C11 123.6(4) . . ?
C20 C19 C18 120.6(5) . . ?
C20 C19 H19A 119.7 . . ?
C18 C19 H19A 119.7 . . ?
C21 C20 C19 120.9(5) . . ?
C21 C20 H20A 119.5 . . ?
C19 C20 H20A 119.5 . . ?
C22 C21 C20 120.3(5) . . ?
C22 C21 H21A 119.9 . . ?
C20 C21 H21A 119.9 . . ?
C21 C22 C23 120.6(5) . . ?
C21 C22 H22A 119.7 . . ?
C23 C22 H22A 119.7 . . ?
C22 C23 C18 119.6(4) . . ?
C22 C23 H23A 120.2 . . ?
C18 C23 H23A 120.2 . . ?
F1 C24 F2 107.1(5) . . ?
F1 C24 F3 104.8(5) . . ?
F2 C24 F3 106.2(4) . . ?
F1 C24 C9 114.8(4) . . ?
F2 C24 C9 113.4(5) . . ?
F3 C24 C9 109.9(5) . . ?
S1 C25 H25A 109.5 . . ?
S1 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
S1 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C9 C26 H26A 109.5 . . ?
C9 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C9 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
C6 C1 C2 C3 -1.4(7) . . . . ?
C1 C2 C3 C4 -0.4(7) . . . . ?
C1 C2 C3 S1 179.7(4) . . . . ?
C25 S1 C3 C4 27.2(5) . . . . ?
C25 S1 C3 C2 -152.9(4) . . . . ?
C2 C3 C4 C5 1.6(6) . . . . ?
S1 C3 C4 C5 -178.4(3) . . . . ?
C3 C4 C5 C6 -1.2(6) . . . . ?
C4 C5 C6 C1 -0.6(6) . . . . ?
C4 C5 C6 C7 -179.9(4) . . . . ?
C2 C1 C6 C5 1.8(6) . . . . ?
C2 C1 C6 C7 -178.8(4) . . . . ?
C10 N1 C7 C6 -177.5(3) . . . . ?
C10 N1 C7 C8 1.2(4) . . . . ?
C5 C6 C7 N1 -174.0(4) . . . . ?
C1 C6 C7 N1 6.6(6) . . . . ?
C5 C6 C7 C8 7.3(6) . . . . ?
C1 C6 C7 C8 -172.0(4) . . . . ?
N1 C7 C8 C9 7.6(5) . . . . ?
C6 C7 C8 C9 -173.5(3) . . . . ?
C7 C8 C9 C26 -139.1(4) . . . . ?
C7 C8 C9 C24 99.3(4) . . . . ?
C7 C8 C9 C10 -11.9(4) . . . . ?
C7 N1 C10 C11 118.0(3) . . . . ?
C7 N1 C10 C9 -9.1(4) . . . . ?
C8 C9 C10 N1 12.8(4) . . . . ?
C26 C9 C10 N1 136.2(4) . . . . ?
C24 C9 C10 N1 -100.8(4) . . . . ?
C8 C9 C10 C11 -108.5(4) . . . . ?
C26 C9 C10 C11 15.0(5) . . . . ?
C24 C9 C10 C11 138.0(4) . . . . ?
N1 C10 C11 O1 -58.9(4) . . . . ?
C9 C10 C11 O1 60.7(4) . . . . ?
N1 C10 C11 C18 62.1(4) . . . . ?
C9 C10 C11 C18 -178.3(3) . . . . ?
N1 C10 C11 C12 -177.3(3) . . . . ?
C9 C10 C11 C12 -57.7(4) . . . . ?
O1 C11 C12 C17 18.9(5) . . . . ?
C18 C11 C12 C17 -98.8(5) . . . . ?
C10 C11 C12 C17 137.8(4) . . . . ?
O1 C11 C12 C13 -164.6(4) . . . . ?
C18 C11 C12 C13 77.7(5) . . . . ?
C10 C11 C12 C13 -45.7(5) . . . . ?
C17 C12 C13 C14 -3.3(7) . . . . ?
C11 C12 C13 C14 -179.9(4) . . . . ?
C12 C13 C14 C15 0.3(9) . . . . ?
C13 C14 C15 C16 2.0(10) . . . . ?
C14 C15 C16 C17 -1.3(10) . . . . ?
C13 C12 C17 C16 4.0(7) . . . . ?
C11 C12 C17 C16 -179.4(5) . . . . ?
C15 C16 C17 C12 -1.7(9) . . . . ?
O1 C11 C18 C19 -39.5(5) . . . . ?
C12 C11 C18 C19 76.2(4) . . . . ?
C10 C11 C18 C19 -159.3(4) . . . . ?
O1 C11 C18 C23 144.3(4) . . . . ?
C12 C11 C18 C23 -100.0(4) . . . . ?
C10 C11 C18 C23 24.5(5) . . . . ?
C23 C18 C19 C20 -0.8(6) . . . . ?
C11 C18 C19 C20 -177.3(4) . . . . ?
C18 C19 C20 C21 1.0(8) . . . . ?
C19 C20 C21 C22 0.1(8) . . . . ?
C20 C21 C22 C23 -1.4(8) . . . . ?
C21 C22 C23 C18 1.5(7) . . . . ?
C19 C18 C23 C22 -0.4(6) . . . . ?
C11 C18 C23 C22 175.8(4) . . . . ?
C8 C9 C24 F1 -55.0(6) . . . . ?
C26 C9 C24 F1 -178.0(4) . . . . ?
C10 C9 C24 F1 53.9(5) . . . . ?
C8 C9 C24 F2 -178.6(4) . . . . ?
C26 C9 C24 F2 58.4(6) . . . . ?
C10 C9 C24 F2 -69.7(6) . . . . ?
C8 C9 C24 F3 62.8(6) . . . . ?
C26 C9 C24 F3 -60.2(6) . . . . ?
C10 C9 C24 F3 171.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.043


# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.821 226 52 ' '
2 0.500 0.500 0.178 226 52 ' '
_platon_squeeze_details          
;
;
####################################################################### 
# 
# 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 1504965'
_audit_update_record             
;
2016-09-19 deposited with the CCDC.
2017-05-25 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 H23 Cl F3 N O3'
_chemical_formula_weight         501.91

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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                   8.5817(2)
_cell_length_b                   10.4128(3)
_cell_length_c                   27.6259(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2468.64(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8505
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      23.16

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9387
_exptl_absorpt_correction_T_max  0.9697
_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  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28833
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4355
_reflns_number_gt                3714
_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)+(0.0345P)²+0.4812P] 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   -0.06(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4355
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0828
_refine_ls_wR_factor_gt          0.0770
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
Cl1 Cl 0.08519(8) 0.55829(5) 0.81950(3) 0.06750(19) Uani 1 1 d . . .
F1 F -0.2643(2) -0.19721(18) 0.74799(7) 0.1196(8) Uani 1 1 d . . .
F2 F -0.5030(3) -0.1350(2) 0.74936(6) 0.1014(6) Uani 1 1 d . . .
F3 F -0.4422(3) -0.32300(17) 0.77430(7) 0.1210(8) Uani 1 1 d . . .
O1 O -0.66972(18) 0.02110(13) 0.84236(6) 0.0590(4) Uani 1 1 d . . .
O2 O -0.76373(19) -0.16606(14) 0.81640(6) 0.0597(4) Uani 1 1 d . . .
O3 O -0.2862(2) 0.03857(17) 0.90063(6) 0.0748(5) Uani 1 1 d . . .
N1 N -0.5385(2) -0.29476(15) 0.87034(6) 0.0465(4) Uani 1 1 d . . .
C1 C -0.6930(3) -0.22176(19) 0.93971(8) 0.0453(5) Uani 1 1 d . . .
C2 C -0.6107(4) -0.1711(2) 0.97769(9) 0.0685(7) Uani 1 1 d . . .
H2A H -0.5109 -0.2007 0.9846 0.082 Uiso 1 1 calc R . .
C3 C -0.6772(5) -0.0753(3) 1.00582(12) 0.0930(10) Uani 1 1 d . . .
H3A H -0.6219 -0.0416 1.0318 0.112 Uiso 1 1 calc R . .
C4 C -0.8232(5) -0.0300(3) 0.99566(14) 0.0909(10) Uani 1 1 d . . .
H4A H -0.8667 0.0351 1.0144 0.109 Uiso 1 1 calc R . .
C5 C -0.9040(4) -0.0806(3) 0.95807(11) 0.0799(8) Uani 1 1 d . . .
H5A H -1.0034 -0.0502 0.9511 0.096 Uiso 1 1 calc R . .
C6 C -0.8404(3) -0.1766(2) 0.93025(9) 0.0616(6) Uani 1 1 d . . .
H6A H -0.8975 -0.2112 0.9048 0.074 Uiso 1 1 calc R . .
C7 C -0.6381(2) -0.45915(19) 0.92092(8) 0.0463(5) Uani 1 1 d . . .
C8 C -0.7177(3) -0.4965(2) 0.96208(9) 0.0573(6) Uani 1 1 d . . .
H8A H -0.7635 -0.4346 0.9817 0.069 Uiso 1 1 calc R . .
C9 C -0.7301(4) -0.6250(3) 0.97447(11) 0.0759(8) Uani 1 1 d . . .
H9A H -0.7836 -0.6489 1.0023 0.091 Uiso 1 1 calc R . .
C10 C -0.6635(4) -0.7164(3) 0.94568(14) 0.0863(10) Uani 1 1 d . . .
H10A H -0.6712 -0.8027 0.9540 0.104 Uiso 1 1 calc R . .
C11 C -0.5854(4) -0.6811(2) 0.90454(12) 0.0827(9) Uani 1 1 d . . .
H11A H -0.5404 -0.7437 0.8850 0.099 Uiso 1 1 calc R . .
C12 C -0.5730(3) -0.5537(2) 0.89186(10) 0.0640(6) Uani 1 1 d . . .
H12A H -0.5207 -0.5309 0.8637 0.077 Uiso 1 1 calc R . .
C13 C -0.1762(3) 0.2470(2) 0.80194(8) 0.0511(5) Uani 1 1 d . . .
H13A H -0.2240 0.2046 0.7763 0.061 Uiso 1 1 calc R . .
C14 C -0.0943(3) 0.3582(2) 0.79317(9) 0.0563(6) Uani 1 1 d . . .
H14A H -0.0874 0.3910 0.7619 0.068 Uiso 1 1 calc R . .
C15 C -0.0232(2) 0.42010(19) 0.83073(9) 0.0494(5) Uani 1 1 d . . .
C16 C -0.0335(3) 0.3743(2) 0.87710(9) 0.0572(6) Uani 1 1 d . . .
H16A H 0.0145 0.4178 0.9024 0.069 Uiso 1 1 calc R . .
C17 C -0.1159(3) 0.2631(2) 0.88585(8) 0.0576(6) Uani 1 1 d . . .
H17A H -0.1228 0.2316 0.9173 0.069 Uiso 1 1 calc R . .
C18 C -0.1889(2) 0.19708(18) 0.84829(8) 0.0426(5) Uani 1 1 d . . .
C19 C -0.2684(2) 0.0730(2) 0.85891(8) 0.0481(5) Uani 1 1 d . . .
C20 C -0.3227(3) -0.0045(2) 0.81612(8) 0.0498(5) Uani 1 1 d . . .
H20A H -0.2407 -0.0030 0.7920 0.060 Uiso 1 1 calc R . .
H20B H -0.4123 0.0388 0.8022 0.060 Uiso 1 1 calc R . .
C21 C -0.3679(2) -0.1458(2) 0.82485(9) 0.0532(6) Uani 1 1 d . . .
C22 C -0.5153(2) -0.15930(18) 0.85746(8) 0.0429(5) Uani 1 1 d . . .
H22A H -0.4949 -0.1122 0.8875 0.052 Uiso 1 1 calc R . .
C23 C -0.6635(3) -0.10539(19) 0.83574(8) 0.0445(5) Uani 1 1 d . . .
C24 C -0.6189(2) -0.32134(18) 0.90774(8) 0.0420(5) Uani 1 1 d . . .
C25 C -0.8130(3) 0.0824(2) 0.82678(12) 0.0829(9) Uani 1 1 d . . .
H25A H -0.8067 0.1730 0.8328 0.124 Uiso 1 1 calc R . .
H25B H -0.8992 0.0469 0.8444 0.124 Uiso 1 1 calc R . .
H25C H -0.8279 0.0678 0.7928 0.124 Uiso 1 1 calc R . .
C26 C -0.2335(3) -0.2196(3) 0.84883(15) 0.0892(10) Uani 1 1 d . . .
H26A H -0.1417 -0.2124 0.8292 0.134 Uiso 1 1 calc R . .
H26B H -0.2616 -0.3084 0.8520 0.134 Uiso 1 1 calc R . .
H26C H -0.2133 -0.1841 0.8803 0.134 Uiso 1 1 calc R . .
C27 C -0.3964(4) -0.2012(3) 0.77450(12) 0.0824(10) 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
Cl1 C15 1.741(2) . ?
F1 C27 1.351(3) . ?
F2 C27 1.339(4) . ?
F3 C27 1.328(3) . ?
O1 C23 1.331(2) . ?
O1 C25 1.451(3) . ?
O2 C23 1.193(3) . ?
O3 C19 1.217(3) . ?
N1 C24 1.273(3) . ?
N1 C22 1.468(2) . ?
C1 C2 1.370(3) . ?
C1 C6 1.375(3) . ?
C1 C24 1.503(3) . ?
C2 C3 1.386(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.369(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.355(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.373(4) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.382(3) . ?
C7 C12 1.388(3) . ?
C7 C24 1.490(3) . ?
C8 C9 1.384(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.366(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.370(5) . ?
C10 H10A 0.9300 . ?
C11 C12 1.376(3) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 C14 1.377(3) . ?
C13 C18 1.386(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.365(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.370(3) . ?
C16 C17 1.378(3) . ?
C16 H16A 0.9300 . ?
C17 C18 1.393(3) . ?
C17 H17A 0.9300 . ?
C18 C19 1.490(3) . ?
C19 C20 1.506(3) . ?
C20 C21 1.540(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C27 1.526(4) . ?
C21 C26 1.536(4) . ?
C21 C22 1.559(3) . ?
C22 C23 1.514(3) . ?
C22 H22A 0.9800 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 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
C23 O1 C25 115.4(2) . . ?
C24 N1 C22 118.64(17) . . ?
C2 C1 C6 119.2(2) . . ?
C2 C1 C24 119.8(2) . . ?
C6 C1 C24 120.9(2) . . ?
C1 C2 C3 119.6(3) . . ?
C1 C2 H2A 120.2 . . ?
C3 C2 H2A 120.2 . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4A 120.3 . . ?
C3 C4 H4A 120.3 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C5 C6 C1 120.6(3) . . ?
C5 C6 H6A 119.7 . . ?
C1 C6 H6A 119.7 . . ?
C8 C7 C12 118.4(2) . . ?
C8 C7 C24 121.8(2) . . ?
C12 C7 C24 119.8(2) . . ?
C7 C8 C9 120.9(3) . . ?
C7 C8 H8A 119.6 . . ?
C9 C8 H8A 119.6 . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
C9 C10 C11 120.1(2) . . ?
C9 C10 H10A 120.0 . . ?
C11 C10 H10A 120.0 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11A 119.7 . . ?
C12 C11 H11A 119.7 . . ?
C11 C12 C7 120.4(3) . . ?
C11 C12 H12A 119.8 . . ?
C7 C12 H12A 119.8 . . ?
C14 C13 C18 121.2(2) . . ?
C14 C13 H13A 119.4 . . ?
C18 C13 H13A 119.4 . . ?
C15 C14 C13 119.4(2) . . ?
C15 C14 H14A 120.3 . . ?
C13 C14 H14A 120.3 . . ?
C14 C15 C16 121.2(2) . . ?
C14 C15 Cl1 119.55(18) . . ?
C16 C15 Cl1 119.28(17) . . ?
C15 C16 C17 119.3(2) . . ?
C15 C16 H16A 120.3 . . ?
C17 C16 H16A 120.3 . . ?
C16 C17 C18 121.0(2) . . ?
C16 C17 H17A 119.5 . . ?
C18 C17 H17A 119.5 . . ?
C13 C18 C17 117.88(19) . . ?
C13 C18 C19 122.87(19) . . ?
C17 C18 C19 119.1(2) . . ?
O3 C19 C18 120.0(2) . . ?
O3 C19 C20 123.1(2) . . ?
C18 C19 C20 116.90(19) . . ?
C19 C20 C21 117.9(2) . . ?
C19 C20 H20A 107.8 . . ?
C21 C20 H20A 107.8 . . ?
C19 C20 H20B 107.8 . . ?
C21 C20 H20B 107.8 . . ?
H20A C20 H20B 107.2 . . ?
C27 C21 C26 108.9(2) . . ?
C27 C21 C20 105.0(2) . . ?
C26 C21 C20 110.88(19) . . ?
C27 C21 C22 111.25(19) . . ?
C26 C21 C22 108.3(2) . . ?
C20 C21 C22 112.40(17) . . ?
N1 C22 C23 109.74(16) . . ?
N1 C22 C21 109.71(16) . . ?
C23 C22 C21 114.75(17) . . ?
N1 C22 H22A 107.4 . . ?
C23 C22 H22A 107.4 . . ?
C21 C22 H22A 107.4 . . ?
O2 C23 O1 123.8(2) . . ?
O2 C23 C22 125.92(18) . . ?
O1 C23 C22 110.25(18) . . ?
N1 C24 C7 117.90(19) . . ?
N1 C24 C1 123.79(18) . . ?
C7 C24 C1 118.30(18) . . ?
O1 C25 H25A 109.5 . . ?
O1 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O1 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C21 C26 H26A 109.5 . . ?
C21 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C21 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
F3 C27 F2 106.7(3) . . ?
F3 C27 F1 106.0(2) . . ?
F2 C27 F1 106.1(3) . . ?
F3 C27 C21 114.4(3) . . ?
F2 C27 C21 112.8(2) . . ?
F1 C27 C21 110.3(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.0(4) . . . . ?
C24 C1 C2 C3 177.3(2) . . . . ?
C1 C2 C3 C4 -0.8(5) . . . . ?
C2 C3 C4 C5 0.9(5) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C4 C5 C6 C1 -0.8(4) . . . . ?
C2 C1 C6 C5 0.8(4) . . . . ?
C24 C1 C6 C5 -176.5(2) . . . . ?
C12 C7 C8 C9 1.0(3) . . . . ?
C24 C7 C8 C9 -178.0(2) . . . . ?
C7 C8 C9 C10 -0.2(4) . . . . ?
C8 C9 C10 C11 -0.3(5) . . . . ?
C9 C10 C11 C12 0.1(5) . . . . ?
C10 C11 C12 C7 0.7(5) . . . . ?
C8 C7 C12 C11 -1.3(4) . . . . ?
C24 C7 C12 C11 177.8(2) . . . . ?
C18 C13 C14 C15 0.5(4) . . . . ?
C13 C14 C15 C16 -0.8(4) . . . . ?
C13 C14 C15 Cl1 178.18(18) . . . . ?
C14 C15 C16 C17 0.7(4) . . . . ?
Cl1 C15 C16 C17 -178.32(18) . . . . ?
C15 C16 C17 C18 -0.2(4) . . . . ?
C14 C13 C18 C17 0.0(3) . . . . ?
C14 C13 C18 C19 -176.3(2) . . . . ?
C16 C17 C18 C13 -0.1(3) . . . . ?
C16 C17 C18 C19 176.3(2) . . . . ?
C13 C18 C19 O3 -174.5(2) . . . . ?
C17 C18 C19 O3 9.3(3) . . . . ?
C13 C18 C19 C20 5.8(3) . . . . ?
C17 C18 C19 C20 -170.4(2) . . . . ?
O3 C19 C20 C21 -14.4(3) . . . . ?
C18 C19 C20 C21 165.30(18) . . . . ?
C19 C20 C21 C27 -172.9(2) . . . . ?
C19 C20 C21 C26 -55.4(3) . . . . ?
C19 C20 C21 C22 66.0(3) . . . . ?
C24 N1 C22 C23 -74.9(2) . . . . ?
C24 N1 C22 C21 158.13(18) . . . . ?
C27 C21 C22 N1 70.9(3) . . . . ?
C26 C21 C22 N1 -48.8(2) . . . . ?
C20 C21 C22 N1 -171.62(19) . . . . ?
C27 C21 C22 C23 -53.1(3) . . . . ?
C26 C21 C22 C23 -172.84(19) . . . . ?
C20 C21 C22 C23 64.3(2) . . . . ?
C25 O1 C23 O2 3.4(3) . . . . ?
C25 O1 C23 C22 -174.9(2) . . . . ?
N1 C22 C23 O2 -24.0(3) . . . . ?
C21 C22 C23 O2 100.0(2) . . . . ?
N1 C22 C23 O1 154.20(17) . . . . ?
C21 C22 C23 O1 -81.7(2) . . . . ?
C22 N1 C24 C7 -178.56(17) . . . . ?
C22 N1 C24 C1 0.4(3) . . . . ?
C8 C7 C24 N1 177.1(2) . . . . ?
C12 C7 C24 N1 -1.9(3) . . . . ?
C8 C7 C24 C1 -1.9(3) . . . . ?
C12 C7 C24 C1 179.1(2) . . . . ?
C2 C1 C24 N1 -88.5(3) . . . . ?
C6 C1 C24 N1 88.7(3) . . . . ?
C2 C1 C24 C7 90.4(3) . . . . ?
C6 C1 C24 C7 -92.3(2) . . . . ?
C26 C21 C27 F3 63.2(3) . . . . ?
C20 C21 C27 F3 -178.0(3) . . . . ?
C22 C21 C27 F3 -56.1(4) . . . . ?
C26 C21 C27 F2 -174.6(2) . . . . ?
C20 C21 C27 F2 -55.8(3) . . . . ?
C22 C21 C27 F2 66.1(3) . . . . ?
C26 C21 C27 F1 -56.2(3) . . . . ?
C20 C21 C27 F1 62.7(3) . . . . ?
C22 C21 C27 F1 -175.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.028
####################################################################### 
# 
# 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 1504966'
_audit_update_record             
;
2016-09-19 deposited with the CCDC.
2017-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 F3 N O2 S'
_chemical_formula_weight         331.35

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'
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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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                   6.2282(2)
_cell_length_b                   7.0351(2)
_cell_length_c                   36.2461(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1588.16(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6174
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      23.13

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8934
_exptl_absorpt_correction_T_max  0.9380
_exptl_absorpt_process_details   ?

_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  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18524
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         1.12
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2804
_reflns_number_gt                2496
_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)+(0.0553P)²+0.4445P] 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   0.00(12)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2804
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1119
_refine_ls_wR_factor_gt          0.1071
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.003
_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 0.84255(15) 0.46780(10) 0.930253(18) 0.0693(2) Uani 1 1 d . . .
O2 O 0.9126(4) 0.3447(3) 1.21257(5) 0.0749(6) Uani 1 1 d . . .
O1 O 0.9243(4) 0.1477(3) 1.16487(6) 0.0824(7) Uani 1 1 d . . .
F1 F 0.5303(4) 0.6104(6) 1.21497(6) 0.1533(14) Uani 1 1 d . . .
F2 F 0.2957(3) 0.7009(4) 1.17521(6) 0.1141(9) Uani 1 1 d . . .
F3 F 0.6055(5) 0.8161(4) 1.17356(11) 0.1660(14) Uani 1 1 d . . .
N1 N 0.8943(3) 0.4570(3) 1.11702(5) 0.0541(5) Uani 1 1 d . . .
C1 C 0.9496(4) 0.4299(4) 1.03834(7) 0.0510(6) Uani 1 1 d . . .
H1A H 1.0623 0.3868 1.0529 0.061 Uiso 1 1 calc R . .
C2 C 0.9685(4) 0.4245(4) 1.00065(7) 0.0539(6) Uani 1 1 d . . .
H2A H 1.0931 0.3763 0.9900 0.065 Uiso 1 1 calc R . .
C3 C 0.8039(5) 0.4902(3) 0.97807(6) 0.0521(6) Uani 1 1 d . . .
C4 C 0.6211(5) 0.5627(4) 0.99432(7) 0.0579(7) Uani 1 1 d . . .
H4A H 0.5108 0.6094 0.9796 0.069 Uiso 1 1 calc R . .
C5 C 0.6003(4) 0.5666(4) 1.03238(7) 0.0559(6) Uani 1 1 d . . .
H5A H 0.4756 0.6150 1.0429 0.067 Uiso 1 1 calc R . .
C6 C 0.7639(4) 0.4990(3) 1.05506(6) 0.0464(6) Uani 1 1 d . . .
C7 C 0.7396(4) 0.4994(3) 1.09555(7) 0.0473(6) Uani 1 1 d . . .
C8 C 0.5357(4) 0.5526(5) 1.11391(7) 0.0641(7) Uani 1 1 d . . .
H8A H 0.4163 0.4806 1.1039 0.077 Uiso 1 1 calc R . .
H8B H 0.5066 0.6871 1.1110 0.077 Uiso 1 1 calc R . .
C9 C 0.5735(4) 0.5030(4) 1.15444(6) 0.0525(6) Uani 1 1 d . . .
C10 C 0.8234(4) 0.4747(4) 1.15524(6) 0.0502(6) Uani 1 1 d . . .
H10A H 0.8898 0.5879 1.1661 0.060 Uiso 1 1 calc R . .
C11 C 0.8925(4) 0.3027(5) 1.17694(7) 0.0562(7) Uani 1 1 d . . .
C12 C 0.9672(8) 0.1855(7) 1.23631(9) 0.1030(13) Uani 1 1 d . . .
H12A H 0.9773 0.2284 1.2614 0.155 Uiso 1 1 calc R . .
H12B H 1.1025 0.1330 1.2288 0.155 Uiso 1 1 calc R . .
H12C H 0.8578 0.0898 1.2345 0.155 Uiso 1 1 calc R . .
C13 C 0.5041(6) 0.6587(7) 1.17921(10) 0.0875(11) Uani 1 1 d . . .
C14 C 0.4533(5) 0.3187(6) 1.16309(11) 0.0974(13) Uani 1 1 d . . .
H14A H 0.3014 0.3416 1.1623 0.146 Uiso 1 1 calc R . .
H14B H 0.4925 0.2751 1.1873 0.146 Uiso 1 1 calc R . .
H14C H 0.4905 0.2237 1.1452 0.146 Uiso 1 1 calc R . .
C15 C 0.5983(7) 0.5517(5) 0.91069(8) 0.0905(12) Uani 1 1 d . . .
H15A H 0.6067 0.5447 0.8843 0.136 Uiso 1 1 calc R . .
H15B H 0.5750 0.6812 0.9180 0.136 Uiso 1 1 calc R . .
H15C H 0.4812 0.4745 0.9192 0.136 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
S1 C3 1.757(2) . ?
S1 C15 1.779(4) . ?
O2 C11 1.331(3) . ?
O2 C12 1.453(4) . ?
O1 C11 1.191(4) . ?
F1 C13 1.350(4) . ?
F2 C13 1.339(4) . ?
F3 C13 1.291(5) . ?
N1 C7 1.274(3) . ?
N1 C10 1.459(3) . ?
C1 C2 1.372(3) . ?
C1 C6 1.393(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.391(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.379(4) . ?
C4 C5 1.386(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.393(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.475(3) . ?
C7 C8 1.481(3) . ?
C8 C9 1.528(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C13 1.481(5) . ?
C9 C14 1.530(5) . ?
C9 C10 1.569(3) . ?
C10 C11 1.506(4) . ?
C10 H10A 0.9800 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C3 S1 C15 104.25(15) . . ?
C11 O2 C12 115.2(3) . . ?
C7 N1 C10 109.3(2) . . ?
C2 C1 C6 121.0(2) . . ?
C2 C1 H1A 119.5 . . ?
C6 C1 H1A 119.5 . . ?
C1 C2 C3 120.9(2) . . ?
C1 C2 H2A 119.6 . . ?
C3 C2 H2A 119.6 . . ?
C4 C3 C2 118.7(2) . . ?
C4 C3 S1 124.6(2) . . ?
C2 C3 S1 116.7(2) . . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C4 C5 C6 120.8(2) . . ?
C4 C5 H5A 119.6 . . ?
C6 C5 H5A 119.6 . . ?
C1 C6 C5 118.0(2) . . ?
C1 C6 C7 121.2(2) . . ?
C5 C6 C7 120.7(2) . . ?
N1 C7 C6 122.0(2) . . ?
N1 C7 C8 115.6(2) . . ?
C6 C7 C8 122.4(2) . . ?
C7 C8 C9 104.0(2) . . ?
C7 C8 H8A 111.0 . . ?
C9 C8 H8A 111.0 . . ?
C7 C8 H8B 111.0 . . ?
C9 C8 H8B 111.0 . . ?
H8A C8 H8B 109.0 . . ?
C13 C9 C8 111.7(3) . . ?
C13 C9 C14 111.1(3) . . ?
C8 C9 C14 108.4(3) . . ?
C13 C9 C10 111.8(2) . . ?
C8 C9 C10 101.51(19) . . ?
C14 C9 C10 112.0(3) . . ?
N1 C10 C11 109.9(2) . . ?
N1 C10 C9 107.05(18) . . ?
C11 C10 C9 113.3(2) . . ?
N1 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
O1 C11 O2 123.0(3) . . ?
O1 C11 C10 126.2(3) . . ?
O2 C11 C10 110.8(3) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
F3 C13 F2 105.5(4) . . ?
F3 C13 F1 108.0(4) . . ?
F2 C13 F1 106.1(3) . . ?
F3 C13 C9 113.3(3) . . ?
F2 C13 C9 112.4(3) . . ?
F1 C13 C9 111.1(4) . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
S1 C15 H15A 109.5 . . ?
S1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
S1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C6 C1 C2 C3 0.8(4) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C1 C2 C3 S1 -177.7(2) . . . . ?
C15 S1 C3 C4 -1.4(3) . . . . ?
C15 S1 C3 C2 176.7(2) . . . . ?
C2 C3 C4 C5 -1.2(4) . . . . ?
S1 C3 C4 C5 176.9(2) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C2 C1 C6 C5 -1.5(4) . . . . ?
C2 C1 C6 C7 178.0(2) . . . . ?
C4 C5 C6 C1 0.8(4) . . . . ?
C4 C5 C6 C7 -178.6(2) . . . . ?
C10 N1 C7 C6 178.5(2) . . . . ?
C10 N1 C7 C8 -0.3(3) . . . . ?
C1 C6 C7 N1 7.9(4) . . . . ?
C5 C6 C7 N1 -172.6(3) . . . . ?
C1 C6 C7 C8 -173.3(3) . . . . ?
C5 C6 C7 C8 6.2(4) . . . . ?
N1 C7 C8 C9 -9.7(4) . . . . ?
C6 C7 C8 C9 171.4(2) . . . . ?
C7 C8 C9 C13 133.4(3) . . . . ?
C7 C8 C9 C14 -103.9(3) . . . . ?
C7 C8 C9 C10 14.1(3) . . . . ?
C7 N1 C10 C11 133.5(2) . . . . ?
C7 N1 C10 C9 10.1(3) . . . . ?
C13 C9 C10 N1 -134.1(3) . . . . ?
C8 C9 C10 N1 -15.0(3) . . . . ?
C14 C9 C10 N1 100.4(3) . . . . ?
C13 C9 C10 C11 104.5(3) . . . . ?
C8 C9 C10 C11 -136.3(2) . . . . ?
C14 C9 C10 C11 -20.9(3) . . . . ?
C12 O2 C11 O1 -2.7(4) . . . . ?
C12 O2 C11 C10 176.7(3) . . . . ?
N1 C10 C11 O1 -26.5(4) . . . . ?
C9 C10 C11 O1 93.2(3) . . . . ?
N1 C10 C11 O2 154.1(2) . . . . ?
C9 C10 C11 O2 -86.2(3) . . . . ?
C8 C9 C13 F3 -60.6(4) . . . . ?
C14 C9 C13 F3 178.3(3) . . . . ?
C10 C9 C13 F3 52.4(4) . . . . ?
C8 C9 C13 F2 58.8(4) . . . . ?
C14 C9 C13 F2 -62.3(4) . . . . ?
C10 C9 C13 F2 171.8(3) . . . . ?
C8 C9 C13 F1 177.6(3) . . . . ?
C14 C9 C13 F1 56.5(4) . . . . ?
C10 C9 C13 F1 -69.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.039
