# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_ef240
_database_code_depnum_ccdc_archive 'CCDC 1024823'
_audit_update_record             
;
2014-09-17 deposited with the CCDC.
2015-01-06 downloaded from the CCDC.
;

_audit_creation_date             2014-05-05T10:52:12-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H20 F5 N1 O2 S1'
_chemical_formula_sum            'C20 H20 F5 N O4 S'
_chemical_formula_weight         465.43
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.7359(6)
_cell_length_b                   14.0228(15)
_cell_length_c                   12.8595(14)
_cell_angle_alpha                90
_cell_angle_beta                 97.839(2)
_cell_angle_gamma                90
_cell_volume                     1024.67(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_number            8195
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.6
_diffrn_reflns_theta_max         26.45
_diffrn_reflns_theta_full        26.45
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_reflns_number_total             4155
_reflns_number_gt                3811
_reflns_threshold_expression     >2σ(I)

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

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

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0568P)²+0.0495P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4155
_refine_ls_number_parameters     322
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.039
_refine_ls_wR_factor_ref         0.0991
_refine_ls_wR_factor_gt          0.0958
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(7)
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.036

#----------------------------------------------------------------------------#
#                   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'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1243(4) 0.19877(18) 0.73574(18) 0.0558(5) Uani 1 1 d . . .
H1 H -0.2481 0.199 0.6809 0.067 Uiso 1 1 calc R . .
C2 C -0.1468(5) 0.1495(2) 0.8274(2) 0.0680(7) Uani 1 1 d . . .
H2 H -0.2858 0.1172 0.834 0.082 Uiso 1 1 calc R . .
C3 C 0.0350(5) 0.1483(2) 0.9082(2) 0.0731(7) Uani 1 1 d . . .
H3 H 0.0208 0.1147 0.9693 0.088 Uiso 1 1 calc R . .
C4 C 0.2380(5) 0.1969(2) 0.89869(19) 0.0712(7) Uani 1 1 d . . .
H4 H 0.3615 0.1964 0.9536 0.085 Uiso 1 1 calc R . .
C5 C 0.2604(4) 0.2467(2) 0.80800(17) 0.0568(5) Uani 1 1 d . . .
H5 H 0.3982 0.2801 0.8025 0.068 Uiso 1 1 calc R . .
C6 C 0.0794(3) 0.24725(15) 0.72541(15) 0.0453(4) Uani 1 1 d . . .
C7 C 0.1030(5) 0.30231(17) 0.62760(19) 0.0565(5) Uani 1 1 d . . .
H7A H -0.0469 0.3025 0.5824 0.068 Uiso 1 1 calc R . .
H7B H 0.1438 0.3679 0.646 0.068 Uiso 1 1 calc R . .
C8 C 0.2144(3) 0.19291(15) 0.50285(15) 0.0443(4) Uani 1 1 d . . .
C9 C 0.4101(3) 0.16125(15) 0.44275(15) 0.0433(4) Uani 1 1 d . . .
H9 H 0.5339 0.2099 0.4492 0.052 Uiso 1 1 calc R . .
C10 C 0.5206(4) 0.06226(16) 0.47775(16) 0.0488(5) Uani 1 1 d . . .
H10 H 0.674 0.073 0.52 0.059 Uiso 1 1 calc R . .
C11 C 0.5092(4) 0.07565(17) 0.29202(17) 0.0496(5) Uani 1 1 d . . .
H11 H 0.6521 0.1124 0.2862 0.06 Uiso 1 1 calc R . .
C12 C 0.3226(3) 0.14361(15) 0.32645(16) 0.0424(4) Uani 1 1 d . A .
H12 H 0.1755 0.1075 0.3229 0.051 Uiso 1 1 calc R . .
C13 C 0.4447(3) 0.02008(16) 0.19207(16) 0.0480(5) Uani 1 1 d . . .
C14 C 0.3711(4) 0.00297(17) 0.54056(18) 0.0545(5) Uani 1 1 d . . .
C15 C 0.2454(4) -0.03681(18) 0.17719(18) 0.0574(6) Uani 1 1 d . . .
H15 H 0.1459 -0.0386 0.2285 0.069 Uiso 1 1 calc R . .
C16 C 0.2270(6) -0.0091(2) 0.7028(3) 0.0829(9) Uani 1 1 d . . .
H16A H 0.0657 0.0015 0.674 0.124 Uiso 1 1 calc R . .
H16B H 0.2558 0.0173 0.7723 0.124 Uiso 1 1 calc R . .
H16C H 0.2585 -0.0763 0.7058 0.124 Uiso 1 1 calc R . .
C17 C 0.1925(5) -0.09088(19) 0.0872(2) 0.0655(6) Uani 1 1 d . . .
H17 H 0.0582 -0.1288 0.0784 0.079 Uiso 1 1 calc R . .
C18 C 0.3384(5) -0.0886(2) 0.01091(19) 0.0660(7) Uani 1 1 d . . .
H18 H 0.303 -0.1249 -0.0498 0.079 Uiso 1 1 calc R . .
C19 C 0.5358(5) -0.0330(2) 0.02462(19) 0.0694(7) Uani 1 1 d . . .
H19 H 0.6354 -0.0317 -0.0267 0.083 Uiso 1 1 calc R . .
C20 C 0.5878(4) 0.0213(2) 0.11422(19) 0.0597(6) Uani 1 1 d . . .
H20 H 0.7217 0.0594 0.1223 0.072 Uiso 1 1 calc R . .
N1 N 0.5568(4) 0.01122(18) 0.38227(16) 0.0605(5) Uani 1 1 d . . .
O1 O 0.2839(2) 0.26125(11) 0.57057(11) 0.0494(3) Uani 1 1 d . . .
O2 O 0.0209(3) 0.15965(15) 0.48889(14) 0.0665(5) Uani 1 1 d . . .
O3 O 0.3785(3) 0.03643(12) 0.63729(12) 0.0616(4) Uani 1 1 d . . .
O4 O 0.2627(4) -0.06552(16) 0.50836(17) 0.0894(7) Uani 1 1 d . . .
S1 S 0.25768(11) 0.25265(5) 0.24748(4) 0.06009(17) Uani 1 1 d . . .
F1 F 0.388(3) 0.3193(5) 0.3253(6) 0.141(5) Uani 0.577(12) 1 d P A 1
F2 F 0.0321(18) 0.2677(6) 0.3015(7) 0.117(3) Uani 0.577(12) 1 d P A 1
F3 F 0.4640(15) 0.2385(8) 0.1866(8) 0.113(3) Uani 0.577(12) 1 d P A 1
F4 F 0.1077(17) 0.1902(4) 0.1625(5) 0.100(2) Uani 0.577(12) 1 d P A 1
F1A F 0.5240(14) 0.2823(9) 0.262(2) 0.152(6) Uani 0.423(12) 1 d P A 2
F2A F 0.0032(14) 0.2374(11) 0.225(2) 0.174(8) Uani 0.423(12) 1 d P A 2
F3A F 0.307(6) 0.2052(8) 0.1461(6) 0.164(8) Uani 0.423(12) 1 d P A 2
F4A F 0.237(4) 0.3152(7) 0.3430(6) 0.123(6) Uani 0.423(12) 1 d P A 2
F5 F 0.1954(4) 0.34434(13) 0.17781(14) 0.1005(6) Uani 1 1 d . A .
H1N H 0.458(5) -0.029(2) 0.372(2) 0.059(8) Uiso 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.374(3) . ?
C1 C2 1.388(4) . ?
C1 H1 0.93 . ?
C2 C3 1.368(4) . ?
C2 H2 0.93 . ?
C3 C4 1.369(4) . ?
C3 H3 0.93 . ?
C4 C5 1.380(4) . ?
C4 H4 0.93 . ?
C5 C6 1.380(3) . ?
C5 H5 0.93 . ?
C6 C7 1.498(3) . ?
C7 O1 1.467(3) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 O2 1.195(2) . ?
C8 O1 1.319(3) . ?
C8 C9 1.514(3) . ?
C9 C12 1.531(3) . ?
C9 C10 1.566(3) . ?
C9 H9 0.98 . ?
C10 N1 1.460(3) . ?
C10 C14 1.506(3) . ?
C10 H10 0.98 . ?
C11 N1 1.467(3) . ?
C11 C13 1.505(3) . ?
C11 C12 1.542(3) . ?
C11 H11 0.98 . ?
C12 S1 1.845(2) . ?
C12 H12 0.98 . ?
C13 C20 1.378(3) . ?
C13 C15 1.386(3) . ?
C14 O4 1.188(3) . ?
C14 O3 1.325(3) . ?
C15 C17 1.382(3) . ?
C15 H15 0.93 . ?
C16 O3 1.439(3) . ?
C16 H16A 0.96 . ?
C16 H16B 0.96 . ?
C16 H16C 0.96 . ?
C17 C18 1.374(4) . ?
C17 H17 0.93 . ?
C18 C19 1.367(4) . ?
C18 H18 0.93 . ?
C19 C20 1.379(4) . ?
C19 H19 0.93 . ?
C20 H20 0.93 . ?
N1 H1N 0.80(3) . ?
S1 F2A 1.465(6) . ?
S1 F1 1.493(5) . ?
S1 F3 1.519(5) . ?
S1 F3A 1.524(6) . ?
S1 F4A 1.528(7) . ?
S1 F2 1.564(5) . ?
S1 F4 1.564(4) . ?
S1 F1A 1.570(9) . ?
S1 F5 1.5798(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.5(2) . . ?
C6 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 120 . . ?
C1 C2 H2 120 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.9(2) . . ?
C1 C6 C7 120.8(2) . . ?
C5 C6 C7 120.3(2) . . ?
O1 C7 C6 111.63(18) . . ?
O1 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
O1 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108 . . ?
O2 C8 O1 124.99(19) . . ?
O2 C8 C9 123.17(19) . . ?
O1 C8 C9 111.84(16) . . ?
C8 C9 C12 112.28(15) . . ?
C8 C9 C10 114.37(17) . . ?
C12 C9 C10 101.73(17) . . ?
C8 C9 H9 109.4 . . ?
C12 C9 H9 109.4 . . ?
C10 C9 H9 109.4 . . ?
N1 C10 C14 109.7(2) . . ?
N1 C10 C9 106.93(17) . . ?
C14 C10 C9 113.91(17) . . ?
N1 C10 H10 108.7 . . ?
C14 C10 H10 108.7 . . ?
C9 C10 H10 108.7 . . ?
N1 C11 C13 110.75(19) . . ?
N1 C11 C12 102.43(16) . . ?
C13 C11 C12 117.76(17) . . ?
N1 C11 H11 108.5 . . ?
C13 C11 H11 108.5 . . ?
C12 C11 H11 108.5 . . ?
C9 C12 C11 103.45(16) . . ?
C9 C12 S1 114.73(15) . . ?
C11 C12 S1 116.74(14) . . ?
C9 C12 H12 107.1 . . ?
C11 C12 H12 107.1 . . ?
S1 C12 H12 107.1 . . ?
C20 C13 C15 117.9(2) . . ?
C20 C13 C11 120.83(19) . . ?
C15 C13 C11 121.19(18) . . ?
O4 C14 O3 124.2(2) . . ?
O4 C14 C10 124.7(2) . . ?
O3 C14 C10 111.11(19) . . ?
C17 C15 C13 121.0(2) . . ?
C17 C15 H15 119.5 . . ?
C13 C15 H15 119.5 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C15 120.0(2) . . ?
C18 C17 H17 120 . . ?
C15 C17 H17 120 . . ?
C19 C18 C17 119.7(2) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 120.3(2) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C13 C20 C19 121.2(2) . . ?
C13 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C10 N1 C11 109.32(19) . . ?
C10 N1 H1N 108(2) . . ?
C11 N1 H1N 105(2) . . ?
C8 O1 C7 116.39(17) . . ?
C14 O3 C16 116.6(2) . . ?
F2A S1 F1 128.1(9) . . ?
F2A S1 F3 134.9(9) . . ?
F1 S1 F3 94.2(5) . . ?
F2A S1 F3A 93.7(10) . . ?
F1 S1 F3A 135.4(10) . . ?
F3 S1 F3A 41.7(8) . . ?
F2A S1 F4A 93.2(9) . . ?
F1 S1 F4A 35.7(5) . . ?
F3 S1 F4A 129.9(7) . . ?
F3A S1 F4A 169.3(8) . . ?
F2A S1 F2 40.9(8) . . ?
F1 S1 F2 89.2(5) . . ?
F3 S1 F2 175.4(4) . . ?
F3A S1 F2 134.4(10) . . ?
F4A S1 F2 53.5(5) . . ?
F2A S1 F4 48.9(8) . . ?
F1 S1 F4 175.1(4) . . ?
F3 S1 F4 87.7(4) . . ?
F3A S1 F4 46.1(9) . . ?
F4A S1 F4 142.0(7) . . ?
F2 S1 F4 88.6(4) . . ?
F2A S1 F1A 171.9(4) . . ?
F1 S1 F1A 50.6(6) . . ?
F3 S1 F1A 44.1(6) . . ?
F3A S1 F1A 85.7(8) . . ?
F4A S1 F1A 86.2(8) . . ?
F2 S1 F1A 139.7(8) . . ?
F4 S1 F1A 131.7(8) . . ?
F2A S1 F5 82.3(3) . . ?
F1 S1 F5 85.6(3) . . ?
F3 S1 F5 86.9(2) . . ?
F3A S1 F5 85.6(3) . . ?
F4A S1 F5 87.3(3) . . ?
F2 S1 F5 90.30(19) . . ?
F4 S1 F5 90.0(2) . . ?
F1A S1 F5 89.6(4) . . ?
F2A S1 C12 96.2(3) . . ?
F1 S1 C12 96.0(2) . . ?
F3 S1 C12 93.6(2) . . ?
F3A S1 C12 93.6(3) . . ?
F4A S1 C12 93.8(3) . . ?
F2 S1 C12 89.11(19) . . ?
F4 S1 C12 88.31(19) . . ?
F1A S1 C12 91.9(3) . . ?
F5 S1 C12 178.21(12) . . ?

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 -0.5(4) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
C2 C1 C6 C7 -178.7(2) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
C4 C5 C6 C7 179.3(2) . . . . ?
C1 C6 C7 O1 -114.7(2) . . . . ?
C5 C6 C7 O1 67.1(3) . . . . ?
O2 C8 C9 C12 40.3(3) . . . . ?
O1 C8 C9 C12 -139.19(18) . . . . ?
O2 C8 C9 C10 -75.0(3) . . . . ?
O1 C8 C9 C10 105.5(2) . . . . ?
C8 C9 C10 N1 138.6(2) . . . . ?
C12 C9 C10 N1 17.3(2) . . . . ?
C8 C9 C10 C14 17.2(2) . . . . ?
C12 C9 C10 C14 -104.06(19) . . . . ?
C8 C9 C12 C11 -157.52(17) . . . . ?
C10 C9 C12 C11 -34.80(19) . . . . ?
C8 C9 C12 S1 74.21(19) . . . . ?
C10 C9 C12 S1 -163.08(13) . . . . ?
N1 C11 C12 C9 40.3(2) . . . . ?
C13 C11 C12 C9 162.05(18) . . . . ?
N1 C11 C12 S1 167.33(15) . . . . ?
C13 C11 C12 S1 -70.9(2) . . . . ?
N1 C11 C13 C20 -114.7(2) . . . . ?
C12 C11 C13 C20 127.9(2) . . . . ?
N1 C11 C13 C15 62.6(3) . . . . ?
C12 C11 C13 C15 -54.7(3) . . . . ?
N1 C10 C14 O4 -13.3(3) . . . . ?
C9 C10 C14 O4 106.5(3) . . . . ?
N1 C10 C14 O3 165.85(19) . . . . ?
C9 C10 C14 O3 -74.4(2) . . . . ?
C20 C13 C15 C17 0.3(4) . . . . ?
C11 C13 C15 C17 -177.2(2) . . . . ?
C13 C15 C17 C18 -0.1(4) . . . . ?
C15 C17 C18 C19 0.2(4) . . . . ?
C17 C18 C19 C20 -0.5(4) . . . . ?
C15 C13 C20 C19 -0.6(4) . . . . ?
C11 C13 C20 C19 176.9(2) . . . . ?
C18 C19 C20 C13 0.7(4) . . . . ?
C14 C10 N1 C11 132.0(2) . . . . ?
C9 C10 N1 C11 8.0(2) . . . . ?
C13 C11 N1 C10 -156.27(19) . . . . ?
C12 C11 N1 C10 -29.9(2) . . . . ?
O2 C8 O1 C7 -3.8(3) . . . . ?
C9 C8 O1 C7 175.60(17) . . . . ?
C6 C7 O1 C8 87.4(2) . . . . ?
O4 C14 O3 C16 -6.0(4) . . . . ?
C10 C14 O3 C16 174.9(2) . . . . ?
C9 C12 S1 F2A -113.2(12) . . . . ?
C11 C12 S1 F2A 125.6(12) . . . . ?
C9 C12 S1 F1 16.3(7) . . . . ?
C11 C12 S1 F1 -104.9(7) . . . . ?
C9 C12 S1 F3 111.0(6) . . . . ?
C11 C12 S1 F3 -10.3(6) . . . . ?
C9 C12 S1 F3A 152.7(12) . . . . ?
C11 C12 S1 F3A 31.5(12) . . . . ?
C9 C12 S1 F4A -19.5(8) . . . . ?
C11 C12 S1 F4A -140.7(8) . . . . ?
C9 C12 S1 F2 -72.8(5) . . . . ?
C11 C12 S1 F2 165.9(5) . . . . ?
C9 C12 S1 F4 -161.5(5) . . . . ?
C11 C12 S1 F4 77.3(5) . . . . ?
C9 C12 S1 F1A 66.8(10) . . . . ?
C11 C12 S1 F1A -54.4(10) . . . . ?
C9 C12 S1 F5 -144(3) . . . . ?
C11 C12 S1 F5 95(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O4 0.80(3) 2.26(3) 2.717(3) 116(2) .

# END of CIF
####################################################################### 
# 
# 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_ef253
_database_code_depnum_ccdc_archive 'CCDC 1024824'
_audit_update_record             
;
2014-09-17 deposited with the CCDC.
2015-01-06 downloaded from the CCDC.
;

_audit_creation_date             2014-04-25T16:56:40-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H21 F5 N2 O1 S1'
_chemical_formula_sum            'C19 H21 F5 N2 O S'
_chemical_formula_weight         420.44
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n 21 a'
_symmetry_space_group_name_Hall  'P -2ac -2n'
_symmetry_Int_Tables_number      33
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, y, -z+1/2'
'-x+1/2, y+1/2, z+1/2'
'-x, y+1/2, -z'

_cell_length_a                   9.2994(9)
_cell_length_b                   12.5496(12)
_cell_length_c                   17.0351(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1988.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.22
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_number            15188
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_full        26.39
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             4061
_reflns_number_gt                2671
_reflns_threshold_expression     >2σ(I)

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

_computing_structure_solution    'SHELXD (Sheldrick, 2002)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0747P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4061
_refine_ls_number_parameters     253
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1393
_refine_ls_wR_factor_gt          0.1212
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_restrained_S_all      0.952
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.10(11)
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.039

#----------------------------------------------------------------------------#
#                   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'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3526(4) 1.0392(3) 0.9313(2) 0.0665(11) Uani 1 1 d . . .
H1 H 0.4034 1.0056 0.8913 0.08 Uiso 1 1 calc R . .
C2 C 0.3283(5) 1.1464(4) 0.9262(3) 0.0685(11) Uani 1 1 d . . .
H2 H 0.3641 1.1844 0.8836 0.082 Uiso 1 1 calc R . .
C3 C 0.2518(5) 1.1983(4) 0.9830(3) 0.0748(12) Uani 1 1 d . . .
H3 H 0.2339 1.271 0.9792 0.09 Uiso 1 1 calc R . .
C4 C 0.2023(5) 1.1410(4) 1.0456(3) 0.0829(14) Uani 1 1 d . . .
H4 H 0.1513 1.1753 1.0852 0.1 Uiso 1 1 calc R . .
C5 C 0.2270(5) 1.0332(4) 1.0506(2) 0.0792(13) Uani 1 1 d . . .
H5 H 0.191 0.9952 1.0931 0.095 Uiso 1 1 calc R . .
C6 C 0.3050(4) 0.9802(3) 0.9930(2) 0.0581(10) Uani 1 1 d . . .
C7 C 0.3330(5) 0.8624(3) 1.0007(2) 0.0732(12) Uani 1 1 d . . .
H7A H 0.4249 0.8516 1.0265 0.088 Uiso 1 1 calc R . .
H7B H 0.2591 0.8308 1.0335 0.088 Uiso 1 1 calc R . .
C8 C 0.3618(4) 0.6942(3) 0.9330(2) 0.0625(10) Uani 1 1 d . . .
H8A H 0.2974 0.6618 0.9709 0.075 Uiso 1 1 calc R . .
H8B H 0.4605 0.6802 0.9482 0.075 Uiso 1 1 calc R . .
C9 C 0.3310(4) 0.6544(3) 0.8498(2) 0.0503(8) Uani 1 1 d . . .
H9 H 0.4192 0.6639 0.8191 0.06 Uiso 1 1 calc R . .
C10 C 0.2184(3) 0.7318(3) 0.81663(19) 0.0439(8) Uani 1 1 d . . .
H10 H 0.1284 0.6943 0.8051 0.053 Uiso 1 1 calc R . .
C11 C 0.1968(4) 0.8120(3) 0.8838(2) 0.0532(9) Uani 1 1 d . . .
H11A H 0.1772 0.8828 0.8636 0.064 Uiso 1 1 calc R . .
H11B H 0.1185 0.7905 0.9179 0.064 Uiso 1 1 calc R . .
C12 C 0.2736(3) 0.7884(3) 0.74409(19) 0.0448(8) Uani 1 1 d . . .
C13 C 0.2102(4) 0.9000(3) 0.6328(2) 0.0566(10) Uani 1 1 d . . .
H13A H 0.1279 0.9023 0.5979 0.068 Uiso 1 1 calc R . .
H13B H 0.2885 0.8662 0.6046 0.068 Uiso 1 1 calc R . .
C14 C 0.2534(4) 1.0120(4) 0.65225(18) 0.0520(8) Uani 1 1 d . . .
C15 C 0.1735(4) 1.0742(4) 0.7026(2) 0.0663(11) Uani 1 1 d . . .
H15 H 0.0928 1.0452 0.7268 0.08 Uiso 1 1 calc R . .
C16 C 0.2109(5) 1.1790(4) 0.7180(3) 0.0818(14) Uani 1 1 d . . .
H16 H 0.1544 1.2202 0.7513 0.098 Uiso 1 1 calc R . .
C17 C 0.3297(5) 1.2213(4) 0.6844(3) 0.0841(14) Uani 1 1 d . . .
H17 H 0.3564 1.291 0.6959 0.101 Uiso 1 1 calc R . .
C18 C 0.4108(5) 1.1622(4) 0.6338(3) 0.0849(14) Uani 1 1 d . . .
H18 H 0.4909 1.1922 0.6098 0.102 Uiso 1 1 calc R . .
C19 C 0.3735(4) 1.0572(4) 0.6181(2) 0.0708(12) Uani 1 1 d . . .
H19 H 0.4301 1.0169 0.5843 0.085 Uiso 1 1 calc R . .
F1 F 0.1293(3) 0.5344(2) 0.87905(18) 0.1025(9) Uani 1 1 d . . .
F2 F 0.3387(3) 0.48622(19) 0.92844(17) 0.1074(10) Uani 1 1 d . . .
F3 F 0.2376(4) 0.3924(2) 0.83713(19) 0.1169(11) Uani 1 1 d . . .
F4 F 0.4309(3) 0.4806(2) 0.8102(2) 0.1284(12) Uani 1 1 d . . .
F5 F 0.2219(4) 0.5289(2) 0.75887(15) 0.1091(10) Uani 1 1 d . . .
N1 N 0.3346(3) 0.8087(2) 0.92508(17) 0.0558(7) Uani 1 1 d . . .
N2 N 0.1740(3) 0.8345(2) 0.70019(17) 0.0497(8) Uani 1 1 d . . .
H2A H 0.0849 0.8254 0.712 0.06 Uiso 1 1 calc R . .
O1 O 0.4016(2) 0.7942(2) 0.72693(14) 0.0612(7) Uani 1 1 d . . .
S1 S 0.28229(13) 0.51402(8) 0.84414(6) 0.0704(3) Uani 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.360(5) . ?
C1 C2 1.367(5) . ?
C1 H1 0.93 . ?
C2 C3 1.366(6) . ?
C2 H2 0.93 . ?
C3 C4 1.366(7) . ?
C3 H3 0.93 . ?
C4 C5 1.375(7) . ?
C4 H4 0.93 . ?
C5 C6 1.389(5) . ?
C5 H5 0.93 . ?
C6 C7 1.508(5) . ?
C7 N1 1.454(5) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 N1 1.466(5) . ?
C8 C9 1.530(5) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 C10 1.536(5) . ?
C9 S1 1.821(4) . ?
C9 H9 0.98 . ?
C10 C12 1.515(5) . ?
C10 C11 1.537(5) . ?
C10 H10 0.98 . ?
C11 N1 1.462(4) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 O1 1.228(4) . ?
C12 N2 1.324(4) . ?
C13 N2 1.451(5) . ?
C13 C14 1.499(5) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C14 C15 1.377(5) . ?
C14 C19 1.382(6) . ?
C15 C16 1.386(6) . ?
C15 H15 0.93 . ?
C16 C17 1.352(7) . ?
C16 H16 0.93 . ?
C17 C18 1.365(7) . ?
C17 H17 0.93 . ?
C18 C19 1.388(6) . ?
C18 H18 0.93 . ?
C19 H19 0.93 . ?
F1 S1 1.563(3) . ?
F2 S1 1.568(3) . ?
F3 S1 1.587(3) . ?
F4 S1 1.556(3) . ?
F5 S1 1.568(3) . ?
N2 H2A 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
C6 C1 C2 122.1(4) . . ?
C6 C1 H1 119 . . ?
C2 C1 H1 119 . . ?
C3 C2 C1 120.7(4) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 118.5(4) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 120.6(4) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 121.0(4) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 117.1(4) . . ?
C1 C6 C7 123.1(4) . . ?
C5 C6 C7 119.9(4) . . ?
N1 C7 C6 112.3(3) . . ?
N1 C7 H7A 109.2 . . ?
C6 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
N1 C8 C9 101.7(3) . . ?
N1 C8 H8A 111.4 . . ?
C9 C8 H8A 111.4 . . ?
N1 C8 H8B 111.4 . . ?
C9 C8 H8B 111.4 . . ?
H8A C8 H8B 109.3 . . ?
C8 C9 C10 105.2(3) . . ?
C8 C9 S1 114.3(3) . . ?
C10 C9 S1 115.0(2) . . ?
C8 C9 H9 107.3 . . ?
C10 C9 H9 107.3 . . ?
S1 C9 H9 107.3 . . ?
C12 C10 C9 111.4(3) . . ?
C12 C10 C11 110.1(3) . . ?
C9 C10 C11 103.3(3) . . ?
C12 C10 H10 110.6 . . ?
C9 C10 H10 110.6 . . ?
C11 C10 H10 110.6 . . ?
N1 C11 C10 103.0(3) . . ?
N1 C11 H11A 111.2 . . ?
C10 C11 H11A 111.2 . . ?
N1 C11 H11B 111.2 . . ?
C10 C11 H11B 111.2 . . ?
H11A C11 H11B 109.1 . . ?
O1 C12 N2 121.2(3) . . ?
O1 C12 C10 123.4(3) . . ?
N2 C12 C10 115.4(3) . . ?
N2 C13 C14 114.7(3) . . ?
N2 C13 H13A 108.6 . . ?
C14 C13 H13A 108.6 . . ?
N2 C13 H13B 108.6 . . ?
C14 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C15 C14 C19 117.7(4) . . ?
C15 C14 C13 121.7(4) . . ?
C19 C14 C13 120.6(3) . . ?
C14 C15 C16 121.4(4) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C17 C16 C15 119.8(5) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 120.3(5) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C19 120.0(4) . . ?
C17 C18 H18 120 . . ?
C19 C18 H18 120 . . ?
C14 C19 C18 120.7(4) . . ?
C14 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C7 N1 C11 113.9(3) . . ?
C7 N1 C8 112.0(3) . . ?
C11 N1 C8 102.9(3) . . ?
C12 N2 C13 122.1(3) . . ?
C12 N2 H2A 118.9 . . ?
C13 N2 H2A 118.9 . . ?
F4 S1 F1 173.79(17) . . ?
F4 S1 F5 90.3(2) . . ?
F1 S1 F5 90.41(18) . . ?
F4 S1 F2 89.1(2) . . ?
F1 S1 F2 89.58(18) . . ?
F5 S1 F2 173.88(16) . . ?
F4 S1 F3 86.86(18) . . ?
F1 S1 F3 87.01(17) . . ?
F5 S1 F3 87.18(17) . . ?
F2 S1 F3 86.70(16) . . ?
F4 S1 C9 93.40(18) . . ?
F1 S1 C9 92.75(16) . . ?
F5 S1 C9 91.32(15) . . ?
F2 S1 C9 94.79(16) . . ?
F3 S1 C9 178.48(19) . . ?

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 -1.2(7) . . . . ?
C1 C2 C3 C4 1.0(7) . . . . ?
C2 C3 C4 C5 -1.0(8) . . . . ?
C3 C4 C5 C6 1.1(7) . . . . ?
C2 C1 C6 C5 1.4(6) . . . . ?
C2 C1 C6 C7 -178.8(4) . . . . ?
C4 C5 C6 C1 -1.3(6) . . . . ?
C4 C5 C6 C7 178.8(4) . . . . ?
C1 C6 C7 N1 -34.0(6) . . . . ?
C5 C6 C7 N1 145.8(4) . . . . ?
N1 C8 C9 C10 -29.3(4) . . . . ?
N1 C8 C9 S1 -156.3(3) . . . . ?
C8 C9 C10 C12 119.6(3) . . . . ?
S1 C9 C10 C12 -113.8(3) . . . . ?
C8 C9 C10 C11 1.4(4) . . . . ?
S1 C9 C10 C11 128.0(3) . . . . ?
C12 C10 C11 N1 -92.0(3) . . . . ?
C9 C10 C11 N1 27.1(3) . . . . ?
C9 C10 C12 O1 -18.5(5) . . . . ?
C11 C10 C12 O1 95.5(4) . . . . ?
C9 C10 C12 N2 163.1(3) . . . . ?
C11 C10 C12 N2 -82.9(3) . . . . ?
N2 C13 C14 C15 -48.1(5) . . . . ?
N2 C13 C14 C19 133.7(4) . . . . ?
C19 C14 C15 C16 0.8(6) . . . . ?
C13 C14 C15 C16 -177.5(4) . . . . ?
C14 C15 C16 C17 -1.4(7) . . . . ?
C15 C16 C17 C18 1.8(8) . . . . ?
C16 C17 C18 C19 -1.7(8) . . . . ?
C15 C14 C19 C18 -0.7(6) . . . . ?
C13 C14 C19 C18 177.6(4) . . . . ?
C17 C18 C19 C14 1.1(7) . . . . ?
C6 C7 N1 C11 -63.8(4) . . . . ?
C6 C7 N1 C8 -180.0(4) . . . . ?
C10 C11 N1 C7 -168.5(3) . . . . ?
C10 C11 N1 C8 -47.1(4) . . . . ?
C9 C8 N1 C7 170.1(3) . . . . ?
C9 C8 N1 C11 47.4(4) . . . . ?
O1 C12 N2 C13 -4.2(5) . . . . ?
C10 C12 N2 C13 174.3(3) . . . . ?
C14 C13 N2 C12 -80.7(4) . . . . ?
C8 C9 S1 F4 -105.4(3) . . . . ?
C10 C9 S1 F4 132.8(3) . . . . ?
C8 C9 S1 F1 73.7(3) . . . . ?
C10 C9 S1 F1 -48.1(3) . . . . ?
C8 C9 S1 F5 164.2(3) . . . . ?
C10 C9 S1 F5 42.4(3) . . . . ?
C8 C9 S1 F2 -16.1(3) . . . . ?
C10 C9 S1 F2 -137.9(3) . . . . ?
C8 C9 S1 F3 154(8) . . . . ?
C10 C9 S1 F3 33(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O1 0.86 2.04 2.866(4) 162.1 2_456

# END of CIF
