# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_Structure-2gh
_database_code_depnum_ccdc_archive 'CCDC 1474239'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-09-30 downloaded from the CCDC.
;
#============================================================================
_audit_creation_date             2016-01-27
_audit_creation_method           CRYSTALS_ver_14.43

_oxford_structure_analysis_title 108lp15
_chemical_name_systematic        .
_chemical_melting_point          '>523 K'

_cell_length_a                   6.8480(1)
_cell_length_b                   20.4301(3)
_cell_length_c                   17.0570(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.3040(11)
_cell_angle_gamma                90
_cell_volume                     2386.33(6)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,-y+1/2,z+1/2
-x+1/2,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C18 H16 F3 N3 O1 S1 
# Dc =      1.06 Fooo =   1128.00 Mu =     14.94 M =    379.40
# Found Formula = C25 H20 F3 N3 O4 S2 
# Dc =      1.52 FOOO =   1128.00 Mu =     25.86 M =    547.58

_chemical_formula_sum            'C25 H20 F3 N3 O4 S2'
_chemical_formula_moiety         'C25 H20 F3 N3 O4 S2'
_chemical_compound_source        ?
_chemical_formula_weight         547.58


_cell_measurement_reflns_used    15563
_cell_measurement_theta_min      4
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       prism
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_max          0.25

_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1128
_exptl_absorpt_coefficient_mu    2.586

# Sheldrick geometric approximatio 0.77 0.77 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.54
_exptl_absorpt_correction_T_max  0.77
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            29782
_reflns_number_total             4979
_diffrn_reflns_av_R_equivalents  0.027
# Number of reflections with Friedels Law is 4979 
# Theoretical number of reflections is about 10002 


_diffrn_reflns_theta_min         3.375
_diffrn_reflns_theta_max         76.279
_diffrn_measured_fraction_theta_max 0.994

_diffrn_reflns_theta_full        74.753
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       16
_reflns_limit_h_min              -8
_reflns_limit_h_max              8
_reflns_limit_k_min              0
_reflns_limit_k_max              25
_reflns_limit_l_min              0
_reflns_limit_l_max              21

_oxford_diffrn_Wilson_B_factor   2.20
_oxford_diffrn_Wilson_scale      0.04

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.39
_refine_diff_density_max         0.28


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         4958
_refine_ls_number_restraints     0
_refine_ls_number_parameters     334
_oxford_refine_ls_R_factor_ref   0.0326
_refine_ls_wR_factor_ref         0.0824
_refine_ls_goodness_of_fit_ref   0.9995
_refine_ls_shift/su_max          0.0014022
_refine_ls_shift/su_mean         0.0000615


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4958
_refine_ls_R_factor_all          0.0326
_refine_ls_wR_factor_all         0.0824

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4681
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_gt          0.0812

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 1.13P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
S1 S 0.66067(4) 0.622276(15) 0.660034(18) 0.0252 1.0000 Uani . . . . . .
O2 O 0.55241(14) 0.68200(5) 0.65512(6) 0.0305 1.0000 Uani . . . . . .
O3 O 0.84485(14) 0.61628(5) 0.62225(6) 0.0333 1.0000 Uani . . . . . .
N4 N 0.69315(16) 0.61030(5) 0.75565(7) 0.0265 1.0000 Uani . . . . . .
C5 C 0.58392(19) 0.64863(6) 0.81343(8) 0.0257 1.0000 Uani . . . . . .
C6 C 0.69755(19) 0.64469(6) 0.89166(8) 0.0259 1.0000 Uani . . . . . .
S7 S 0.79956(5) 0.561059(16) 0.889851(19) 0.0299 1.0000 Uani . . . . . .
C8 C 0.79546(19) 0.55625(6) 0.78607(8) 0.0270 1.0000 Uani . . . . . .
N9 N 0.86406(17) 0.51257(6) 0.74234(7) 0.0301 1.0000 Uani . . . . . .
C10 C 0.9886(2) 0.46204(7) 0.76963(8) 0.0310 1.0000 Uani . . . . . .
C11 C 0.9494(2) 0.39840(7) 0.74573(9) 0.0365 1.0000 Uani . . . . . .
C12 C 1.0817(3) 0.34885(8) 0.76366(10) 0.0470 1.0000 Uani . . . . . .
C13 C 1.2490(3) 0.36159(10) 0.80435(10) 0.0552 1.0000 Uani . . . . . .
C14 C 1.2887(3) 0.42467(11) 0.82851(12) 0.0583 1.0000 Uani . . . . . .
C15 C 1.1591(3) 0.47518(9) 0.81108(11) 0.0465 1.0000 Uani . . . . . .
C16 C 0.8651(2) 0.69549(7) 0.90043(9) 0.0327 1.0000 Uani . . . . . .
C17 C 1.0015(2) 0.70425(8) 0.83153(11) 0.0428 1.0000 Uani . . . . . .
F18 F 1.15299(16) 0.74240(6) 0.85210(8) 0.0640 1.0000 Uani . . . . . .
F19 F 1.08229(13) 0.64889(5) 0.80389(6) 0.0475 1.0000 Uani . . . . . .
F20 F 0.91459(15) 0.73381(5) 0.76967(6) 0.0513 1.0000 Uani . . . . . .
C21 C 0.7844(3) 0.76274(7) 0.92371(11) 0.0438 1.0000 Uani . . . . . .
C22 C 0.6937(3) 0.75830(8) 1.00422(10) 0.0488 1.0000 Uani . . . . . .
C23 C 0.5444(3) 0.70491(8) 1.00828(9) 0.0412 1.0000 Uani . . . . . .
C24 C 0.5513(2) 0.65015(7) 0.95917(8) 0.0317 1.0000 Uani . . . . . .
C25 C 0.4098(2) 0.60121(9) 0.96769(10) 0.0410 1.0000 Uani . . . . . .
C26 C 0.2619(3) 0.60710(12) 1.02268(12) 0.0572 1.0000 Uani . . . . . .
C27 C 0.2538(3) 0.66252(13) 1.06960(11) 0.0655 1.0000 Uani . . . . . .
C28 C 0.3923(3) 0.70968(11) 1.06251(10) 0.0580 1.0000 Uani . . . . . .
C29 C 0.50839(19) 0.55747(6) 0.62859(7) 0.0253 1.0000 Uani . . . . . .
C30 C 0.3080(2) 0.56697(7) 0.62769(8) 0.0293 1.0000 Uani . . . . . .
C31 C 0.18807(19) 0.51597(7) 0.60433(8) 0.0303 1.0000 Uani . . . . . .
C32 C 0.2717(2) 0.45713(7) 0.58384(8) 0.0281 1.0000 Uani . . . . . .
N33 N 0.14345(18) 0.40218(6) 0.56159(7) 0.0324 1.0000 Uani . . . . . .
O34 O -0.03185(15) 0.41335(6) 0.55370(7) 0.0411 1.0000 Uani . . . . . .
O35 O 0.21701(18) 0.34840(6) 0.55299(8) 0.0479 1.0000 Uani . . . . . .
C36 C 0.4718(2) 0.44722(7) 0.58332(8) 0.0308 1.0000 Uani . . . . . .
C37 C 0.5915(2) 0.49837(7) 0.60531(8) 0.0296 1.0000 Uani . . . . . .
H51 H 0.5723 0.6936 0.7951 0.0310 1.0000 Uiso R . . . . .
H52 H 0.4528 0.6301 0.8199 0.0304 1.0000 Uiso R . . . . .
H111 H 0.8277 0.3896 0.7180 0.0449 1.0000 Uiso R . . . . .
H121 H 1.0524 0.3040 0.7475 0.0588 1.0000 Uiso R . . . . .
H131 H 1.3384 0.3269 0.8155 0.0640 1.0000 Uiso R . . . . .
H141 H 1.4084 0.4339 0.8565 0.0708 1.0000 Uiso R . . . . .
H151 H 1.1894 0.5196 0.8266 0.0566 1.0000 Uiso R . . . . .
H161 H 0.9487 0.6799 0.9442 0.0391 1.0000 Uiso R . . . . .
H211 H 0.8957 0.7937 0.9243 0.0530 1.0000 Uiso R . . . . .
H212 H 0.6837 0.7758 0.8858 0.0519 1.0000 Uiso R . . . . .
H221 H 0.6293 0.7997 1.0166 0.0578 1.0000 Uiso R . . . . .
H222 H 0.7978 0.7495 1.0438 0.0571 1.0000 Uiso R . . . . .
H251 H 0.4203 0.5627 0.9353 0.0504 1.0000 Uiso R . . . . .
H261 H 0.1655 0.5724 1.0272 0.0702 1.0000 Uiso R . . . . .
H271 H 0.1472 0.6669 1.1075 0.0805 1.0000 Uiso R . . . . .
H281 H 0.3870 0.7474 1.0963 0.0711 1.0000 Uiso R . . . . .
H301 H 0.2500 0.6081 0.6432 0.0352 1.0000 Uiso R . . . . .
H311 H 0.0483 0.5221 0.6039 0.0363 1.0000 Uiso R . . . . .
H361 H 0.5253 0.4062 0.5680 0.0375 1.0000 Uiso R . . . . .
H371 H 0.7310 0.4935 0.6048 0.0361 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.30(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 . O2 . 1.4299(10) yes
S1 . O3 . 1.4248(10) yes
S1 . N4 . 1.6630(11) yes
S1 . C29 . 1.7670(14) yes
N4 . C5 . 1.4670(16) yes
N4 . C8 . 1.4054(16) yes
C5 . C6 . 1.5431(18) yes
C5 . H51 . 0.974 no
C5 . H52 . 0.981 no
C6 . S7 . 1.8463(13) yes
C6 . C16 . 1.5536(19) yes
C6 . C24 . 1.5343(19) yes
S7 . C8 . 1.7731(14) yes
C8 . N9 . 1.2559(18) yes
N9 . C10 . 1.4160(17) yes
C10 . C11 . 1.388(2) yes
C10 . C15 . 1.388(2) yes
C11 . C12 . 1.391(2) yes
C11 . H111 . 0.973 no
C12 . C13 . 1.362(3) yes
C12 . H121 . 0.977 no
C13 . C14 . 1.380(3) yes
C13 . H131 . 0.954 no
C14 . C15 . 1.392(2) yes
C14 . H141 . 0.966 no
C15 . H151 . 0.968 no
C16 . C17 . 1.516(2) yes
C16 . C21 . 1.534(2) yes
C16 . H161 . 0.991 no
C17 . F18 . 1.3429(18) yes
C17 . F19 . 1.345(2) yes
C17 . F20 . 1.351(2) yes
C21 . C22 . 1.513(3) yes
C21 . H211 . 0.991 no
C21 . H212 . 0.979 no
C22 . C23 . 1.497(3) yes
C22 . H221 . 0.977 no
C22 . H222 . 0.996 no
C23 . C24 . 1.399(2) yes
C23 . C28 . 1.400(3) yes
C24 . C25 . 1.401(2) yes
C25 . C26 . 1.389(2) yes
C25 . H251 . 0.965 no
C26 . C27 . 1.388(3) yes
C26 . H261 . 0.972 no
C27 . C28 . 1.358(3) yes
C27 . H271 . 0.982 no
C28 . H281 . 0.963 no
C29 . C30 . 1.3858(18) yes
C29 . C37 . 1.3935(19) yes
C30 . C31 . 1.384(2) yes
C30 . H301 . 0.967 no
C31 . C32 . 1.377(2) yes
C31 . H311 . 0.965 no
C32 . N33 . 1.4737(18) yes
C32 . C36 . 1.3858(19) yes
N33 . O34 . 1.2286(16) yes
N33 . O35 . 1.2180(17) yes
C36 . C37 . 1.379(2) yes
C36 . H361 . 0.951 no
C37 . H371 . 0.961 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 . S1 . O3 . 120.45(6) yes
O2 . S1 . N4 . 104.46(6) yes
O3 . S1 . N4 . 108.48(6) yes
O2 . S1 . C29 . 108.46(6) yes
O3 . S1 . C29 . 108.70(6) yes
N4 . S1 . C29 . 105.25(6) yes
S1 . N4 . C5 . 120.95(9) yes
S1 . N4 . C8 . 122.78(9) yes
C5 . N4 . C8 . 115.24(11) yes
N4 . C5 . C6 . 107.25(10) yes
N4 . C5 . H51 . 109.2 no
C6 . C5 . H51 . 111.5 no
N4 . C5 . H52 . 109.8 no
C6 . C5 . H52 . 109.9 no
H51 . C5 . H52 . 109.1 no
C5 . C6 . S7 . 102.88(9) yes
C5 . C6 . C16 . 114.65(11) yes
S7 . C6 . C16 . 109.91(9) yes
C5 . C6 . C24 . 108.48(10) yes
S7 . C6 . C24 . 109.17(9) yes
C16 . C6 . C24 . 111.34(11) yes
C6 . S7 . C8 . 93.67(6) yes
S7 . C8 . N4 . 109.29(9) yes
S7 . C8 . N9 . 128.92(10) yes
N4 . C8 . N9 . 121.76(13) yes
C8 . N9 . C10 . 123.33(12) yes
N9 . C10 . C11 . 118.09(13) yes
N9 . C10 . C15 . 122.01(14) yes
C11 . C10 . C15 . 119.44(14) yes
C10 . C11 . C12 . 119.48(16) yes
C10 . C11 . H111 . 118.6 no
C12 . C11 . H111 . 121.9 no
C11 . C12 . C13 . 121.21(17) yes
C11 . C12 . H121 . 119.2 no
C13 . C12 . H121 . 119.5 no
C12 . C13 . C14 . 119.64(15) yes
C12 . C13 . H131 . 119.8 no
C14 . C13 . H131 . 120.6 no
C13 . C14 . C15 . 120.29(18) yes
C13 . C14 . H141 . 119.8 no
C15 . C14 . H141 . 119.9 no
C14 . C15 . C10 . 119.93(17) yes
C14 . C15 . H151 . 120.1 no
C10 . C15 . H151 . 120.0 no
C6 . C16 . C17 . 117.51(12) yes
C6 . C16 . C21 . 110.87(12) yes
C17 . C16 . C21 . 108.63(13) yes
C6 . C16 . H161 . 106.4 no
C17 . C16 . H161 . 105.4 no
C21 . C16 . H161 . 107.4 no
C16 . C17 . F18 . 110.15(14) yes
C16 . C17 . F19 . 115.39(13) yes
F18 . C17 . F19 . 105.11(13) yes
C16 . C17 . F20 . 112.81(13) yes
F18 . C17 . F20 . 106.32(13) yes
F19 . C17 . F20 . 106.41(14) yes
C16 . C21 . C22 . 109.37(13) yes
C16 . C21 . H211 . 107.3 no
C22 . C21 . H211 . 110.4 no
C16 . C21 . H212 . 109.0 no
C22 . C21 . H212 . 109.0 no
H211 . C21 . H212 . 111.9 no
C21 . C22 . C23 . 111.68(13) yes
C21 . C22 . H221 . 109.4 no
C23 . C22 . H221 . 108.1 no
C21 . C22 . H222 . 109.3 no
C23 . C22 . H222 . 108.9 no
H221 . C22 . H222 . 109.4 no
C22 . C23 . C24 . 122.01(15) yes
C22 . C23 . C28 . 119.38(17) yes
C24 . C23 . C28 . 118.62(18) yes
C6 . C24 . C23 . 122.14(14) yes
C6 . C24 . C25 . 118.74(13) yes
C23 . C24 . C25 . 118.90(15) yes
C24 . C25 . C26 . 121.03(18) yes
C24 . C25 . H251 . 118.0 no
C26 . C25 . H251 . 121.0 no
C25 . C26 . C27 . 119.5(2) yes
C25 . C26 . H261 . 119.2 no
C27 . C26 . H261 . 121.3 no
C26 . C27 . C28 . 119.82(18) yes
C26 . C27 . H271 . 119.1 no
C28 . C27 . H271 . 121.1 no
C23 . C28 . C27 . 122.14(19) yes
C23 . C28 . H281 . 118.8 no
C27 . C28 . H281 . 119.1 no
S1 . C29 . C30 . 118.76(10) yes
S1 . C29 . C37 . 119.64(10) yes
C30 . C29 . C37 . 121.60(13) yes
C29 . C30 . C31 . 118.93(13) yes
C29 . C30 . H301 . 121.8 no
C31 . C30 . H301 . 119.3 no
C30 . C31 . C32 . 118.90(12) yes
C30 . C31 . H311 . 119.4 no
C32 . C31 . H311 . 121.7 no
C31 . C32 . N33 . 118.85(12) yes
C31 . C32 . C36 . 122.79(13) yes
N33 . C32 . C36 . 118.36(12) yes
C32 . N33 . O34 . 117.85(12) yes
C32 . N33 . O35 . 118.17(12) yes
O34 . N33 . O35 . 123.97(13) yes
C32 . C36 . C37 . 118.29(13) yes
C32 . C36 . H361 . 120.8 no
C37 . C36 . H361 . 120.9 no
C29 . C37 . C36 . 119.43(12) yes
C29 . C37 . H371 . 120.0 no
C36 . C37 . H371 . 120.5 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C31 . H311 . O3 1_455 132.86 0.965 2.397 3.134(2) yes
C37 . H371 . O34 1_655 136.76 0.961 2.468 3.236(2) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 27/01/16 at 16:30:35
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   5,X'S) H   (  51,X'S) H   (  52,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) H   ( 212,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 222,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) 
END                                                                             
;


_iucr_refine_instructions_details_restraints 
;
#
# Punched on 27/01/16 at 16:30:35
#
#LIST     16                                                                    
NO 
END                                                                             
;

# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
1 0 3 x .
####################################################################### 
# 
# 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_Structure-2kb
_database_code_depnum_ccdc_archive 'CCDC 1474240'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-09-30 downloaded from the CCDC.
;
#============================================================================
_audit_creation_date             2016-01-27
_audit_creation_method           CRYSTALS_ver_14.43

_oxford_structure_analysis_title 109lp15
_chemical_name_systematic        .
_chemical_melting_point          '414-415 K'

_cell_length_a                   7.4653(2)
_cell_length_b                   9.9343(4)
_cell_length_c                   17.6618(5)
_cell_angle_alpha                89.239(3)
_cell_angle_beta                 85.681(2)
_cell_angle_gamma                72.865(3)
_cell_volume                     1248.09(7)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C26 H22 F3 N3 O4 S2 
# Dc =      1.49 Fooo =    580.00 Mu =     24.87 M =    561.60
# Found Formula = C26 H22 F3 N3 O4 S2 
# Dc =      1.49 FOOO =    580.00 Mu =     24.87 M =    561.60

_chemical_formula_sum            'C26 H22 F3 N3 O4 S2'
_chemical_formula_moiety         'C26 H22 F3 N3 O4 S2'
_chemical_compound_source        .
_chemical_formula_weight         561.60


_cell_measurement_reflns_used    15005
_cell_measurement_theta_min      5
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.12
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_max          0.19

_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             580
_exptl_absorpt_coefficient_mu    2.487

# Sheldrick geometric approximatio 0.72 0.74 
# No experimental values of Tmin/max available 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_T_max  0.74
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            25529
_reflns_number_total             5208
_diffrn_reflns_av_R_equivalents  0.048
# Number of reflections with Friedels Law is 5208 
# Theoretical number of reflections is about 10463 


_diffrn_reflns_theta_min         4.658
_diffrn_reflns_theta_max         76.282
_diffrn_measured_fraction_theta_max 0.993

_diffrn_reflns_theta_full        74.757
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              -12
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              22

_oxford_diffrn_Wilson_B_factor   1.84
_oxford_diffrn_Wilson_scale      0.02

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.54
_refine_diff_density_max         0.58


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         5188
_refine_ls_number_restraints     0
_refine_ls_number_parameters     343
_oxford_refine_ls_R_factor_ref   0.0363
_refine_ls_wR_factor_ref         0.0978
_refine_ls_goodness_of_fit_ref   1.0039
_refine_ls_shift/su_max          0.0004761
_refine_ls_shift/su_mean         0.0000375


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5188
_refine_ls_R_factor_all          0.0363
_refine_ls_wR_factor_all         0.0978

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                5042
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_gt          0.0970

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.06P)² + 0.68P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
S1 S 0.46594(5) 0.83087(4) 0.356594(19) 0.0234 1.0000 Uani . . . . . .
O2 O 0.36561(15) 0.96265(12) 0.39281(6) 0.0304 1.0000 Uani . . . . . .
O3 O 0.36892(15) 0.75351(13) 0.31732(6) 0.0316 1.0000 Uani . . . . . .
N4 N 0.62488(17) 0.86910(13) 0.29619(7) 0.0242 1.0000 Uani . . . . . .
C5 C 0.73982(19) 0.76438(15) 0.24383(8) 0.0214 1.0000 Uani . . . . . .
S6 S 0.82697(5) 0.84914(4) 0.166727(19) 0.0235 1.0000 Uani . . . . . .
C7 C 0.99140(18) 0.69631(14) 0.11495(7) 0.0183 1.0000 Uani . . . . . .
C8 C 0.89866(19) 0.57692(14) 0.11957(8) 0.0200 1.0000 Uani . . . . . .
C9 C 0.8640(2) 0.52810(15) 0.20010(8) 0.0218 1.0000 Uani . . . . . .
N10 N 0.75916(17) 0.63595(13) 0.25529(7) 0.0230 1.0000 Uani . . . . . .
C11 C 1.1827(2) 0.65904(15) 0.15202(8) 0.0224 1.0000 Uani . . . . . .
C12 C 1.3169(2) 0.51624(16) 0.12616(9) 0.0271 1.0000 Uani . . . . . .
F13 F 1.27968(13) 0.40677(10) 0.16262(6) 0.0337 1.0000 Uani . . . . . .
F14 F 1.31811(13) 0.48932(10) 0.05171(5) 0.0333 1.0000 Uani . . . . . .
F15 F 1.49543(13) 0.50560(11) 0.13946(7) 0.0432 1.0000 Uani . . . . . .
C16 C 1.2780(2) 0.77477(17) 0.13650(9) 0.0280 1.0000 Uani . . . . . .
C17 C 1.3258(2) 0.78719(17) 0.05209(10) 0.0295 1.0000 Uani . . . . . .
C18 C 1.1633(2) 0.79158(15) 0.00520(8) 0.0238 1.0000 Uani . . . . . .
C19 C 1.00568(19) 0.75355(14) 0.03441(8) 0.0198 1.0000 Uani . . . . . .
C20 C 0.8546(2) 0.77312(16) -0.01104(8) 0.0255 1.0000 Uani . . . . . .
C21 C 0.8634(3) 0.82120(16) -0.08494(9) 0.0311 1.0000 Uani . . . . . .
C22 C 1.0242(3) 0.84999(17) -0.11491(9) 0.0339 1.0000 Uani . . . . . .
C23 C 1.1708(2) 0.83662(17) -0.06981(9) 0.0318 1.0000 Uani . . . . . .
C24 C 0.6811(2) 0.99428(15) 0.30974(8) 0.0235 1.0000 Uani . . . . . .
C25 C 0.8473(2) 0.98146(17) 0.34269(9) 0.0308 1.0000 Uani . . . . . .
C26 C 0.9072(3) 1.10028(19) 0.35050(10) 0.0361 1.0000 Uani . . . . . .
C27 C 0.8008(3) 1.23016(17) 0.32548(10) 0.0332 1.0000 Uani . . . . . .
C28 C 0.6339(2) 1.24207(17) 0.29345(9) 0.0329 1.0000 Uani . . . . . .
C29 C 0.5727(2) 1.12412(17) 0.28519(9) 0.0284 1.0000 Uani . . . . . .
C30 C 0.5885(2) 0.72094(16) 0.42758(8) 0.0238 1.0000 Uani . . . . . .
C31 C 0.6267(2) 0.78321(17) 0.49168(9) 0.0296 1.0000 Uani . . . . . .
C32 C 0.7141(2) 0.69831(18) 0.54933(9) 0.0309 1.0000 Uani . . . . . .
C33 C 0.7627(2) 0.55416(17) 0.53982(8) 0.0269 1.0000 Uani . . . . . .
N34 N 0.85418(19) 0.46306(17) 0.60108(8) 0.0350 1.0000 Uani . . . . . .
O35 O 0.93359(19) 0.33960(14) 0.58632(8) 0.0444 1.0000 Uani . . . . . .
O36 O 0.8443(2) 0.51632(18) 0.66346(8) 0.0558 1.0000 Uani . . . . . .
C37 C 0.7284(2) 0.49006(16) 0.47565(9) 0.0276 1.0000 Uani . . . . . .
C38 C 0.6381(2) 0.57540(17) 0.41871(8) 0.0259 1.0000 Uani . . . . . .
H81 H 0.9760 0.4968 0.0890 0.0240 1.0000 Uiso R . . . . .
H82 H 0.7774 0.6101 0.0967 0.0238 1.0000 Uiso R . . . . .
H91 H 0.9866 0.4817 0.2216 0.0258 1.0000 Uiso R . . . . .
H92 H 0.7926 0.4599 0.1974 0.0266 1.0000 Uiso R . . . . .
H111 H 1.1580 0.6538 0.2071 0.0238 1.0000 Uiso R . . . . .
H161 H 1.3912 0.7554 0.1646 0.0336 1.0000 Uiso R . . . . .
H162 H 1.1896 0.8640 0.1555 0.0339 1.0000 Uiso R . . . . .
H171 H 1.3622 0.8725 0.0434 0.0348 1.0000 Uiso R . . . . .
H172 H 1.4330 0.7060 0.0356 0.0355 1.0000 Uiso R . . . . .
H201 H 0.7451 0.7525 0.0094 0.0303 1.0000 Uiso R . . . . .
H211 H 0.7568 0.8322 -0.1142 0.0374 1.0000 Uiso R . . . . .
H221 H 1.0353 0.8799 -0.1666 0.0403 1.0000 Uiso R . . . . .
H231 H 1.2843 0.8591 -0.0891 0.0372 1.0000 Uiso R . . . . .
H251 H 0.9192 0.8945 0.3592 0.0368 1.0000 Uiso R . . . . .
H261 H 1.0209 1.0929 0.3728 0.0442 1.0000 Uiso R . . . . .
H271 H 0.8486 1.3105 0.3306 0.0384 1.0000 Uiso R . . . . .
H281 H 0.5591 1.3317 0.2752 0.0400 1.0000 Uiso R . . . . .
H291 H 0.4571 1.1310 0.2617 0.0340 1.0000 Uiso R . . . . .
H311 H 0.5930 0.8809 0.4967 0.0356 1.0000 Uiso R . . . . .
H321 H 0.7413 0.7373 0.5950 0.0373 1.0000 Uiso R . . . . .
H371 H 0.7648 0.3914 0.4714 0.0331 1.0000 Uiso R . . . . .
H381 H 0.6091 0.5357 0.3755 0.0296 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          6.67(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 . O2 . 1.4340(11) yes
S1 . O3 . 1.4191(12) yes
S1 . N4 . 1.6597(12) yes
S1 . C30 . 1.7745(15) yes
N4 . C5 . 1.4331(18) yes
N4 . C24 . 1.4528(19) yes
C5 . S6 . 1.7736(14) yes
C5 . N10 . 1.2565(19) yes
S6 . C7 . 1.8488(14) yes
C7 . C8 . 1.5381(18) yes
C7 . C11 . 1.5580(18) yes
C7 . C19 . 1.5328(18) yes
C8 . C9 . 1.5249(18) yes
C8 . H81 . 0.975 no
C8 . H82 . 0.984 no
C9 . N10 . 1.4591(18) yes
C9 . H91 . 0.997 no
C9 . H92 . 0.981 no
C11 . C12 . 1.528(2) yes
C11 . C16 . 1.532(2) yes
C11 . H111 . 0.980 no
C12 . F13 . 1.3441(18) yes
C12 . F14 . 1.3442(19) yes
C12 . F15 . 1.3442(17) yes
C16 . C17 . 1.519(2) yes
C16 . H161 . 0.982 no
C16 . H162 . 0.982 no
C17 . C18 . 1.509(2) yes
C17 . H171 . 0.970 no
C17 . H172 . 0.983 no
C18 . C19 . 1.400(2) yes
C18 . C23 . 1.395(2) yes
C19 . C20 . 1.399(2) yes
C20 . C21 . 1.387(2) yes
C20 . H201 . 0.945 no
C21 . C22 . 1.380(3) yes
C21 . H211 . 0.959 no
C22 . C23 . 1.376(3) yes
C22 . H221 . 0.962 no
C23 . H231 . 0.974 no
C24 . C25 . 1.382(2) yes
C24 . C29 . 1.389(2) yes
C25 . C26 . 1.392(2) yes
C25 . H251 . 0.929 no
C26 . C27 . 1.387(2) yes
C26 . H261 . 0.945 no
C27 . C28 . 1.380(3) yes
C27 . H271 . 0.973 no
C28 . C29 . 1.390(2) yes
C28 . H281 . 0.967 no
C29 . H291 . 0.970 no
C30 . C31 . 1.385(2) yes
C30 . C38 . 1.391(2) yes
C31 . C32 . 1.388(2) yes
C31 . H311 . 0.932 no
C32 . C33 . 1.379(2) yes
C32 . H321 . 0.960 no
C33 . N34 . 1.4756(19) yes
C33 . C37 . 1.384(2) yes
N34 . O35 . 1.217(2) yes
N34 . O36 . 1.216(2) yes
C37 . C38 . 1.388(2) yes
C37 . H371 . 0.939 no
C38 . H381 . 0.932 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 . S1 . O3 . 120.45(7) yes
O2 . S1 . N4 . 104.55(7) yes
O3 . S1 . N4 . 108.76(7) yes
O2 . S1 . C30 . 106.74(7) yes
O3 . S1 . C30 . 108.18(7) yes
N4 . S1 . C30 . 107.51(6) yes
S1 . N4 . C5 . 120.31(10) yes
S1 . N4 . C24 . 118.97(9) yes
C5 . N4 . C24 . 118.76(11) yes
N4 . C5 . S6 . 109.06(10) yes
N4 . C5 . N10 . 120.47(13) yes
S6 . C5 . N10 . 130.41(11) yes
C5 . S6 . C7 . 101.00(6) yes
S6 . C7 . C8 . 106.87(9) yes
S6 . C7 . C11 . 108.14(9) yes
C8 . C7 . C11 . 113.50(11) yes
S6 . C7 . C19 . 102.41(9) yes
C8 . C7 . C19 . 112.97(11) yes
C11 . C7 . C19 . 112.09(11) yes
C7 . C8 . C9 . 114.20(11) yes
C7 . C8 . H81 . 109.4 no
C9 . C8 . H81 . 109.3 no
C7 . C8 . H82 . 108.3 no
C9 . C8 . H82 . 108.5 no
H81 . C8 . H82 . 106.8 no
C8 . C9 . N10 . 117.01(11) yes
C8 . C9 . H91 . 109.6 no
N10 . C9 . H91 . 106.0 no
C8 . C9 . H92 . 107.8 no
N10 . C9 . H92 . 106.8 no
H91 . C9 . H92 . 109.4 no
C9 . N10 . C5 . 121.50(12) yes
C7 . C11 . C12 . 113.27(11) yes
C7 . C11 . C16 . 110.44(12) yes
C12 . C11 . C16 . 109.93(12) yes
C7 . C11 . H111 . 108.4 no
C12 . C11 . H111 . 106.8 no
C16 . C11 . H111 . 107.8 no
C11 . C12 . F13 . 113.47(12) yes
C11 . C12 . F14 . 113.93(12) yes
F13 . C12 . F14 . 105.89(12) yes
C11 . C12 . F15 . 111.65(12) yes
F13 . C12 . F15 . 104.98(12) yes
F14 . C12 . F15 . 106.21(13) yes
C11 . C16 . C17 . 111.19(12) yes
C11 . C16 . H161 . 109.7 no
C17 . C16 . H161 . 110.8 no
C11 . C16 . H162 . 107.6 no
C17 . C16 . H162 . 109.2 no
H161 . C16 . H162 . 108.2 no
C16 . C17 . C18 . 112.55(12) yes
C16 . C17 . H171 . 108.9 no
C18 . C17 . H171 . 109.0 no
C16 . C17 . H172 . 108.9 no
C18 . C17 . H172 . 108.9 no
H171 . C17 . H172 . 108.5 no
C17 . C18 . C19 . 122.47(13) yes
C17 . C18 . C23 . 118.40(14) yes
C19 . C18 . C23 . 119.12(14) yes
C7 . C19 . C18 . 122.16(12) yes
C7 . C19 . C20 . 119.44(12) yes
C18 . C19 . C20 . 118.37(13) yes
C19 . C20 . C21 . 121.39(14) yes
C19 . C20 . H201 . 118.7 no
C21 . C20 . H201 . 119.9 no
C20 . C21 . C22 . 119.78(15) yes
C20 . C21 . H211 . 118.5 no
C22 . C21 . H211 . 121.7 no
C21 . C22 . C23 . 119.39(14) yes
C21 . C22 . H221 . 121.3 no
C23 . C22 . H221 . 119.4 no
C18 . C23 . C22 . 121.74(15) yes
C18 . C23 . H231 . 117.2 no
C22 . C23 . H231 . 121.0 no
N4 . C24 . C25 . 119.57(13) yes
N4 . C24 . C29 . 119.46(14) yes
C25 . C24 . C29 . 120.85(14) yes
C24 . C25 . C26 . 119.29(15) yes
C24 . C25 . H251 . 120.6 no
C26 . C25 . H251 . 120.1 no
C25 . C26 . C27 . 120.25(16) yes
C25 . C26 . H261 . 120.1 no
C27 . C26 . H261 . 119.6 no
C26 . C27 . C28 . 119.98(15) yes
C26 . C27 . H271 . 118.0 no
C28 . C27 . H271 . 122.0 no
C27 . C28 . C29 . 120.33(15) yes
C27 . C28 . H281 . 120.8 no
C29 . C28 . H281 . 118.8 no
C28 . C29 . C24 . 119.30(15) yes
C28 . C29 . H291 . 120.9 no
C24 . C29 . H291 . 119.8 no
S1 . C30 . C31 . 118.67(12) yes
S1 . C30 . C38 . 119.50(11) yes
C31 . C30 . C38 . 121.80(14) yes
C30 . C31 . C32 . 119.23(15) yes
C30 . C31 . H311 . 120.8 no
C32 . C31 . H311 . 119.9 no
C31 . C32 . C33 . 118.38(15) yes
C31 . C32 . H321 . 121.9 no
C33 . C32 . H321 . 119.8 no
C32 . C33 . N34 . 118.77(14) yes
C32 . C33 . C37 . 123.20(14) yes
N34 . C33 . C37 . 118.03(14) yes
C33 . N34 . O35 . 118.20(14) yes
C33 . N34 . O36 . 117.69(15) yes
O35 . N34 . O36 . 124.12(15) yes
C33 . C37 . C38 . 118.19(14) yes
C33 . C37 . H371 . 120.4 no
C38 . C37 . H371 . 121.4 no
C30 . C38 . C37 . 119.18(14) yes
C30 . C38 . H381 . 120.4 no
C37 . C38 . H381 . 120.4 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C9 . H91 . O36 2_766 140.98 0.997 2.473 3.308(2) yes
C25 . H251 . O35 2_766 171.32 0.929 2.477 3.398(2) yes
C26 . H261 . O2 1_655 151.46 0.945 2.566 3.426(2) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 27/01/16 at 16:41:46
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  82,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  92,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) H   ( 162,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) 
END                                                                             
;


_iucr_refine_instructions_details_restraints 
;
#
# Punched on 27/01/16 at 16:41:46
#
#LIST     16                                                                    
NO 
END                                                                             
;

# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
1 0 3 x .
####################################################################### 
# 
# 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_Structure-2oa
_database_code_depnum_ccdc_archive 'CCDC 1474241'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-09-30 downloaded from the CCDC.
;
#============================================================================
_audit_creation_date             2016-04-14
_audit_creation_method           CRYSTALS_ver_14.61_build_5555

_oxford_structure_analysis_title 107lp15
_chemical_name_systematic        .
_chemical_melting_point          136-138

_refine_special_details          
;
Although the structure solved well, on initial refinement 
the displacement ellipsoids were found to be highly prolate.
The non-centro-symmetric subgroups of the space group, P2₁/n 
(i.e. P2₁ and Pn) were considered.  Both space groups were 
examined, but particularly P2₁ as the molecule is chiral.  In
both cases, twinning was also considered, but in each case, 
there was no improvement in the displacement ellipsoids.  The
raw diffraction data were also examined for additional 
reflections, and precession images constructed but there was no
evidence of any non-Bragg scattering.  For these reasons, the 
final structure was refined in the centrosymmetric space group
P2₁/n.  This was also tested for twinning using ROTAX, but 
although a tentative twin law was found, the twin scale factor 
refined to zero.

In order to maintain sensible geometric parameters, the final 
model was refined with "whole molecule disorder", leading to a
poor data to parameter ratio and an unstable refinement.  So, in 
order to prevent the refinement diverging, copious same distance,
thermal similarity and vibrational restraints were used.  In the 
case were two atoms were in particularly close proximity, the 
ADPs were constrained to be identical.  Despite this, there is 
still a significant residual peak in the difference Fourier map
close to the sulphur atom, which, together with the high 
R-indices suggest that the model is not ideal.  Nevertheless,
despite the poor result, the structure is in agreement with the
spectroscopic data and other structures and is included for
completeness.
;

_cell_length_a                   15.2695(4)
_cell_length_b                   5.9545(2)
_cell_length_c                   19.0281(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.540(3)
_cell_angle_gamma                90
_cell_volume                     1729.45(10)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,-y+1/2,z+1/2
-x+1/2,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C18 H17 F3 N2 O1 S1 
# Dc =      1.41 Fooo =    760.00 Mu =     20.22 M =    366.41
# Found Formula = C18 H17 F3 N2.00 O1.00 S1.00 
# Dc =      1.41 FOOO =    760.00 Mu =     20.22 M =    366.41

_chemical_formula_sum            'C18 H17 F3 N2 O1 S1'
_chemical_formula_moiety         'C18 H17 F3 N2 O1 S1'
_chemical_compound_source        .
_chemical_formula_weight         366.41


_cell_measurement_reflns_used    3913
_cell_measurement_theta_min      4
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       needle
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.100
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_max          0.180

_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             760.000
_exptl_absorpt_coefficient_mu    2.022

# Sheldrick geometric approximatio 0.75 0.82 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.82
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            3587
_reflns_number_total             3587
_diffrn_reflns_av_R_equivalents  0.017
# Number of reflections with Friedels Law is 3587 
# Theoretical number of reflections is about 7229 


_diffrn_reflns_theta_min         3.664
_diffrn_reflns_theta_max         76.067
_diffrn_measured_fraction_theta_max 0.987

_diffrn_reflns_theta_full        73.785
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       23
_reflns_limit_h_min              -19
_reflns_limit_h_max              19
_reflns_limit_k_min              0
_reflns_limit_k_max              7
_reflns_limit_l_min              0
_reflns_limit_l_max              23

_oxford_diffrn_Wilson_B_factor   3.74
_oxford_diffrn_Wilson_scale      0.05

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.86
_refine_diff_density_max         1.22


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         3575
_refine_ls_number_restraints     949
_refine_ls_number_parameters     422
_oxford_refine_ls_R_factor_ref   0.1033
_refine_ls_wR_factor_ref         0.2648
_refine_ls_goodness_of_fit_ref   0.9831
_refine_ls_shift/su_max          0.0028015
_refine_ls_shift/su_mean         0.0003353


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3575
_refine_ls_R_factor_all          0.1033
_refine_ls_wR_factor_all         0.2648

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3209
_refine_ls_R_factor_gt           0.0976
_refine_ls_wR_factor_gt          0.2580

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.430E+04 0.726E+04 0.443E+04 0.182E+04 407. 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
S1 S 0.4518(8) 0.362(2) 0.6644(8) 0.0430 0.513(4) Uani . . P 1 1 .
C2 C 0.4741(4) 0.2123(13) 0.5832(4) 0.0501 0.513(4) Uani D . P 1 1 .
N3 N 0.5443(5) 0.2526(11) 0.5456(3) 0.0532 0.513(4) Uani D . P 1 1 .
C4 C 0.6245(8) 0.378(3) 0.5635(6) 0.0651 0.513(4) Uani D . P 1 1 .
C5 C 0.6288(4) 0.4621(11) 0.6381(3) 0.0621 0.513(4) Uani D . P 1 1 .
C6 C 0.5465(4) 0.5425(13) 0.6726(3) 0.0546 0.513(4) Uani D . P 1 1 .
N7 N 0.4189(4) 0.0287(9) 0.5714(3) 0.0496 0.513(4) Uani D . P 1 1 .
C8 C 0.3369(3) 0.0214(8) 0.6056(3) 0.0413 0.513(4) Uani D . P 1 1 .
C9 C 0.3089(4) -0.1716(9) 0.6361(4) 0.0612 0.513(4) Uani D . P 1 1 .
C10 C 0.2269(4) -0.1795(9) 0.6666(4) 0.0675 0.513(4) Uani D . P 1 1 .
C11 C 0.1729(2) -0.0010(9) 0.6640(3) 0.0669 0.513(4) Uani D . P 1 1 .
C12 C 0.2004(3) 0.1921(9) 0.6348(3) 0.0560 0.513(4) Uani D . P 1 1 .
C13 C 0.2808(3) 0.2042(8) 0.6032(3) 0.0488 0.513(4) Uani D . P 1 1 .
C14 C 0.7014(2) 0.6311(7) 0.6410(2) 0.0743 0.513(4) Uani D . P 1 1 .
F15 F 0.6746(4) 0.8328(9) 0.6185(4) 0.0898 0.513(4) Uani D . P 1 1 .
F16 F 0.7679(3) 0.5707(9) 0.6010(3) 0.0733 0.513(4) Uani D . P 1 1 .
F17 F 0.7341(3) 0.6583(11) 0.7064(3) 0.0872 0.513(4) Uani D . P 1 1 .
C18 C 0.5516(5) 0.6215(10) 0.7476(3) 0.0436 0.513(4) Uani D . P 1 1 .
C19 C 0.5857(6) 0.4833(10) 0.8007(4) 0.0471 0.513(4) Uani D . P 1 1 .
C20 C 0.5882(7) 0.5513(11) 0.8696(3) 0.0508 0.513(4) Uani D . P 1 1 .
C21 C 0.5606(8) 0.7696(11) 0.8859(3) 0.0535 0.513(4) Uani D . P 1 1 .
C22 C 0.5294(8) 0.9112(11) 0.8332(4) 0.0496 0.513(4) Uani D . P 1 1 .
C23 C 0.5187(7) 0.8287(13) 0.7660(3) 0.0457 0.513(4) Uani D . P 1 1 .
O24 O 0.5602(8) 0.8392(13) 0.9547(4) 0.0752 0.513(4) Uani D . P 1 1 .
C25 C 0.6030(16) 0.713(3) 1.0066(5) 0.0983 0.513(4) Uani D . P 1 1 .
S31 S 0.4650(9) 0.328(2) 0.6696(9) 0.0430 0.487(4) Uani . . P 1 2 .
C32 C 0.4791(4) 0.1857(14) 0.5946(4) 0.0494 0.487(4) Uani D . P 1 2 .
N33 N 0.5534(5) 0.1860(10) 0.5652(4) 0.0468 0.487(4) Uani D . P 1 2 .
C34 C 0.6047(9) 0.396(2) 0.5620(7) 0.0651 0.487(4) Uani D . P 1 2 .
C35 C 0.6094(4) 0.5481(11) 0.6255(3) 0.0631 0.487(4) Uani D . P 1 2 .
C36 C 0.5732(4) 0.4272(11) 0.6895(3) 0.0449 0.487(4) Uani D . P 1 2 .
N37 N 0.4104(4) 0.0819(10) 0.5595(3) 0.0496 0.487(4) Uani D . P 1 2 .
C38 C 0.3295(3) 0.0532(9) 0.5947(3) 0.0496 0.487(4) Uani D . P 1 2 .
C39 C 0.3185(4) -0.1216(11) 0.6415(4) 0.0632 0.487(4) Uani D . P 1 2 .
C40 C 0.2386(4) -0.1483(10) 0.6750(4) 0.0679 0.487(4) Uani D . P 1 2 .
C41 C 0.1711(3) -0.0111(11) 0.6607(3) 0.0635 0.487(4) Uani D . P 1 2 .
C42 C 0.1810(3) 0.1596(11) 0.6145(4) 0.0708 0.487(4) Uani D . P 1 2 .
C43 C 0.2611(4) 0.1956(10) 0.5821(4) 0.0623 0.487(4) Uani D . P 1 2 .
C44 C 0.6959(2) 0.6635(7) 0.6390(2) 0.0758 0.487(4) Uani D . P 1 2 .
F45 F 0.7523(4) 0.5329(10) 0.6745(4) 0.0885 0.487(4) Uani D . P 1 2 .
F46 F 0.6870(3) 0.8519(8) 0.6765(3) 0.0739 0.487(4) Uani D . P 1 2 .
F47 F 0.7340(4) 0.7210(12) 0.5793(3) 0.0907 0.487(4) Uani D . P 1 2 .
C48 C 0.5695(6) 0.5587(11) 0.7576(3) 0.0439 0.487(4) Uani D . P 1 2 .
C49 C 0.6051(7) 0.4715(11) 0.8198(4) 0.0526 0.487(4) Uani D . P 1 2 .
C50 C 0.6036(8) 0.5912(13) 0.8818(4) 0.0567 0.487(4) Uani D . P 1 2 .
C51 C 0.5630(8) 0.8013(13) 0.8821(3) 0.0566 0.487(4) Uani D . P 1 2 .
C52 C 0.5208(7) 0.8823(13) 0.8217(4) 0.0500 0.487(4) Uani D . P 1 2 .
C53 C 0.5303(7) 0.7685(13) 0.7594(3) 0.0478 0.487(4) Uani D . P 1 2 .
O54 O 0.5614(7) 0.9243(12) 0.9434(3) 0.0588 0.487(4) Uani D . P 1 2 .
C55 C 0.5977(15) 0.834(2) 1.0061(6) 0.1027 0.487(4) Uani D . P 1 2 .
H41 H 0.6747 0.2817 0.5575 0.0782 0.513(4) Uiso R . P 1 1 .
H42 H 0.6265 0.5090 0.5329 0.0781 0.513(4) Uiso R . P 1 1 .
H51 H 0.6488 0.3361 0.6672 0.0752 0.513(4) Uiso R . P 1 1 .
H61 H 0.5293 0.6784 0.6463 0.0652 0.513(4) Uiso R . P 1 1 .
H91 H 0.3448 -0.2992 0.6364 0.0740 0.513(4) Uiso R . P 1 1 .
H101 H 0.2096 -0.3114 0.6889 0.0821 0.513(4) Uiso R . P 1 1 .
H111 H 0.1172 -0.0114 0.6826 0.0801 0.513(4) Uiso R . P 1 1 .
H121 H 0.1652 0.3208 0.6356 0.0672 0.513(4) Uiso R . P 1 1 .
H131 H 0.2970 0.3372 0.5810 0.0584 0.513(4) Uiso R . P 1 1 .
H191 H 0.6069 0.3409 0.7887 0.0571 0.513(4) Uiso R . P 1 1 .
H201 H 0.6083 0.4545 0.9043 0.0611 0.513(4) Uiso R . P 1 1 .
H221 H 0.5160 1.0600 0.8432 0.0589 0.513(4) Uiso R . P 1 1 .
H231 H 0.4894 0.9141 0.7318 0.0542 0.513(4) Uiso R . P 1 1 .
H251 H 0.6037 0.7960 1.0497 0.1469 0.513(4) Uiso R . P 1 1 .
H252 H 0.6626 0.6836 0.9938 0.1470 0.513(4) Uiso R . P 1 1 .
H253 H 0.5727 0.5733 1.0138 0.1470 0.513(4) Uiso R . P 1 1 .
H341 H 0.6641 0.3578 0.5503 0.0782 0.487(4) Uiso R . P 1 2 .
H342 H 0.5783 0.4882 0.5253 0.0784 0.487(4) Uiso R . P 1 2 .
H351 H 0.5676 0.6679 0.6140 0.0763 0.487(4) Uiso R . P 1 2 .
H361 H 0.6090 0.2943 0.6990 0.0539 0.487(4) Uiso R . P 1 2 .
H391 H 0.3640 -0.2223 0.6506 0.0762 0.487(4) Uiso R . P 1 2 .
H401 H 0.2318 -0.2639 0.7072 0.0821 0.487(4) Uiso R . P 1 2 .
H411 H 0.1180 -0.0334 0.6827 0.0761 0.487(4) Uiso R . P 1 2 .
H421 H 0.1347 0.2552 0.6040 0.0850 0.487(4) Uiso R . P 1 2 .
H431 H 0.2671 0.3167 0.5514 0.0752 0.487(4) Uiso R . P 1 2 .
H491 H 0.6303 0.3289 0.8198 0.0632 0.487(4) Uiso R . P 1 2 .
H501 H 0.6296 0.5327 0.9225 0.0680 0.487(4) Uiso R . P 1 2 .
H521 H 0.4873 1.0120 0.8236 0.0601 0.487(4) Uiso R . P 1 2 .
H531 H 0.5102 0.8341 0.7167 0.0584 0.487(4) Uiso R . P 1 2 .
H551 H 0.5923 0.9429 1.0432 0.1518 0.487(4) Uiso R . P 1 2 .
H552 H 0.6590 0.8016 1.0004 0.1519 0.487(4) Uiso R . P 1 2 .
H553 H 0.5674 0.6998 1.0193 0.1519 0.487(4) Uiso R . P 1 2 .
H71 H 0.4357 -0.0898 0.5411 0.0591 0.513(4) Uiso R . P 1 1 .
H371 H 0.4166 0.0300 0.5127 0.0591 0.487(4) Uiso R . P 1 2 .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          5.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 . C2 . 1.83(2) yes
S1 . C6 . 1.804(17) yes
C2 . N3 . 1.327(7) yes
C2 . N7 . 1.394(5) yes
N3 . C4 . 1.467(8) yes
C4 . C5 . 1.506(8) yes
C4 . H41 . 0.966 no
C4 . H42 . 0.973 no
C5 . C6 . 1.510(7) yes
C5 . C14 . 1.497(4) yes
C5 . H51 . 0.976 no
C6 . C18 . 1.502(6) yes
C6 . H61 . 0.984 no
N7 . C8 . 1.427(5) yes
N7 . H71 . 0.950 no
C8 . C9 . 1.362(5) yes
C8 . C13 . 1.386(5) yes
C9 . C10 . 1.395(5) yes
C9 . H91 . 0.937 no
C10 . C11 . 1.345(5) yes
C10 . H101 . 0.934 no
C11 . C12 . 1.349(5) yes
C11 . H111 . 0.932 no
C12 . C13 . 1.383(5) yes
C12 . H121 . 0.936 no
C13 . H131 . 0.934 no
C14 . F15 . 1.336(5) yes
C14 . F16 . 1.334(4) yes
C14 . F17 . 1.339(5) yes
C18 . C19 . 1.393(5) yes
C18 . C23 . 1.381(5) yes
C19 . C20 . 1.372(5) yes
C19 . H191 . 0.937 no
C20 . C21 . 1.404(5) yes
C20 . H201 . 0.922 no
C21 . C22 . 1.384(5) yes
C21 . O24 . 1.374(5) yes
C22 . C23 . 1.376(5) yes
C22 . H221 . 0.930 no
C23 . H231 . 0.931 no
O24 . C25 . 1.390(9) yes
C25 . H251 . 0.958 no
C25 . H252 . 0.964 no
C25 . H253 . 0.963 no
S31 . C32 . 1.68(2) yes
S31 . C36 . 1.787(17) yes
C32 . N33 . 1.280(7) yes
C32 . N37 . 1.375(5) yes
N33 . C34 . 1.480(9) yes
C34 . C35 . 1.509(8) yes
C34 . H341 . 0.967 no
C34 . H342 . 0.966 no
C35 . C36 . 1.531(7) yes
C35 . C44 . 1.505(4) yes
C35 . H351 . 0.978 no
C36 . C48 . 1.516(6) yes
C36 . H361 . 0.976 no
N37 . C38 . 1.431(5) yes
N37 . H371 . 0.950 no
C38 . C39 . 1.383(5) yes
C38 . C43 . 1.362(5) yes
C39 . C40 . 1.400(5) yes
C39 . H391 . 0.930 no
C40 . C41 . 1.338(6) yes
C40 . H401 . 0.930 no
C41 . C42 . 1.354(6) yes
C41 . H411 . 0.932 no
C42 . C43 . 1.401(5) yes
C42 . H421 . 0.925 no
C43 . H431 . 0.935 no
C44 . F45 . 1.331(5) yes
C44 . F46 . 1.338(5) yes
C44 . F47 . 1.335(5) yes
C48 . C49 . 1.391(5) yes
C48 . C53 . 1.386(5) yes
C49 . C50 . 1.378(5) yes
C49 . H491 . 0.932 no
C50 . C51 . 1.396(5) yes
C50 . H501 . 0.928 no
C51 . C52 . 1.389(5) yes
C51 . O54 . 1.378(5) yes
C52 . C53 . 1.377(5) yes
C52 . H521 . 0.928 no
C53 . H531 . 0.945 no
O54 . C55 . 1.409(9) yes
C55 . H551 . 0.962 no
C55 . H552 . 0.965 no
C55 . H553 . 0.962 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . S1 . C6 . 101.4(8) yes
S1 . C2 . N3 . 122.6(7) yes
S1 . C2 . N7 . 113.2(6) yes
N3 . C2 . N7 . 123.3(6) yes
C2 . N3 . C4 . 130.5(7) yes
N3 . C4 . C5 . 113.7(8) yes
N3 . C4 . H41 . 109.2 no
C5 . C4 . H41 . 107.1 no
N3 . C4 . H42 . 108.0 no
C5 . C4 . H42 . 107.2 no
H41 . C4 . H42 . 111.6 no
C4 . C5 . C6 . 120.0(7) yes
C4 . C5 . C14 . 105.7(5) yes
C6 . C5 . C14 . 113.3(4) yes
C4 . C5 . H51 . 106.5 no
C6 . C5 . H51 . 104.4 no
C14 . C5 . H51 . 106.0 no
C5 . C6 . S1 . 116.6(7) yes
C5 . C6 . C18 . 119.3(5) yes
S1 . C6 . C18 . 106.8(7) yes
C5 . C6 . H61 . 104.7 no
S1 . C6 . H61 . 104.0 no
C18 . C6 . H61 . 103.3 no
C2 . N7 . C8 . 118.96(7) yes
C2 . N7 . H71 . 120.5 no
C8 . N7 . H71 . 120.5 no
N7 . C8 . C9 . 120.65(6) yes
N7 . C8 . C13 . 120.74(6) yes
C9 . C8 . C13 . 118.38(6) yes
C8 . C9 . C10 . 120.13(7) yes
C8 . C9 . H91 . 119.8 no
C10 . C9 . H91 . 120.1 no
C9 . C10 . C11 . 120.93(7) yes
C9 . C10 . H101 . 119.0 no
C11 . C10 . H101 . 120.1 no
C10 . C11 . C12 . 119.42(7) yes
C10 . C11 . H111 . 119.8 no
C12 . C11 . H111 . 120.7 no
C11 . C12 . C13 . 120.89(7) yes
C11 . C12 . H121 . 120.4 no
C13 . C12 . H121 . 118.8 no
C8 . C13 . C12 . 120.05(7) yes
C8 . C13 . H131 . 120.6 no
C12 . C13 . H131 . 119.3 no
C5 . C14 . F15 . 111.86(5) yes
C5 . C14 . F16 . 111.88(5) yes
F15 . C14 . F16 . 106.96(5) yes
C5 . C14 . F17 . 111.84(5) yes
F15 . C14 . F17 . 106.99(5) yes
F16 . C14 . F17 . 106.99(5) yes
C6 . C18 . C19 . 120.82(6) yes
C6 . C18 . C23 . 120.76(6) yes
C19 . C18 . C23 . 118.36(6) yes
C18 . C19 . C20 . 121.28(7) yes
C18 . C19 . H191 . 118.9 no
C20 . C19 . H191 . 119.8 no
C19 . C20 . C21 . 118.88(7) yes
C19 . C20 . H201 . 120.0 no
C21 . C20 . H201 . 121.1 no
C20 . C21 . C22 . 120.26(6) yes
C20 . C21 . O24 . 119.89(7) yes
C22 . C21 . O24 . 119.76(7) yes
C21 . C22 . C23 . 119.02(7) yes
C21 . C22 . H221 . 120.4 no
C23 . C22 . H221 . 120.6 no
C18 . C23 . C22 . 121.38(7) yes
C18 . C23 . H231 . 118.8 no
C22 . C23 . H231 . 119.8 no
C21 . O24 . C25 . 120.001(11) yes
O24 . C25 . H251 . 108.9 no
O24 . C25 . H252 . 110.4 no
H251 . C25 . H252 . 108.7 no
O24 . C25 . H253 . 110.5 no
H251 . C25 . H253 . 108.5 no
H252 . C25 . H253 . 109.8 no
C32 . S31 . C36 . 102.0(9) yes
S31 . C32 . N33 . 120.5(8) yes
S31 . C32 . N37 . 121.8(6) yes
N33 . C32 . N37 . 117.5(7) yes
C32 . N33 . C34 . 119.7(8) yes
N33 . C34 . C35 . 119.2(9) yes
N33 . C34 . H341 . 108.0 no
C35 . C34 . H341 . 107.6 no
N33 . C34 . H342 . 107.3 no
C35 . C34 . H342 . 104.5 no
H341 . C34 . H342 . 110.2 no
C34 . C35 . C36 . 110.2(7) yes
C34 . C35 . C44 . 115.6(5) yes
C36 . C35 . C44 . 114.4(4) yes
C34 . C35 . H351 . 104.0 no
C36 . C35 . H351 . 105.8 no
C44 . C35 . H351 . 105.6 no
C35 . C36 . S31 . 109.8(6) yes
C35 . C36 . C48 . 117.3(5) yes
S31 . C36 . C48 . 107.3(8) yes
C35 . C36 . H361 . 108.5 no
S31 . C36 . H361 . 106.3 no
C48 . C36 . H361 . 107.1 no
C32 . N37 . C38 . 118.88(7) yes
C32 . N37 . H371 . 120.5 no
C38 . N37 . H371 . 120.6 no
N37 . C38 . C39 . 120.81(6) yes
N37 . C38 . C43 . 120.75(6) yes
C39 . C38 . C43 . 118.44(6) yes
C38 . C39 . C40 . 120.04(7) yes
C38 . C39 . H391 . 120.2 no
C40 . C39 . H391 . 119.8 no
C39 . C40 . C41 . 120.97(9) yes
C39 . C40 . H401 . 120.0 no
C41 . C40 . H401 . 119.1 no
C40 . C41 . C42 . 119.44(9) yes
C40 . C41 . H411 . 119.8 no
C42 . C41 . H411 . 120.8 no
C41 . C42 . C43 . 120.94(9) yes
C41 . C42 . H421 . 120.4 no
C43 . C42 . H421 . 118.7 no
C42 . C43 . C38 . 120.11(7) yes
C42 . C43 . H431 . 119.7 no
C38 . C43 . H431 . 120.2 no
C35 . C44 . F45 . 111.86(5) yes
C35 . C44 . F46 . 111.86(5) yes
F45 . C44 . F46 . 106.98(5) yes
C35 . C44 . F47 . 111.88(5) yes
F45 . C44 . F47 . 106.97(5) yes
F46 . C44 . F47 . 106.97(5) yes
C36 . C48 . C49 . 120.81(6) yes
C36 . C48 . C53 . 120.82(6) yes
C49 . C48 . C53 . 118.37(6) yes
C48 . C49 . C50 . 121.35(7) yes
C48 . C49 . H491 . 119.4 no
C50 . C49 . H491 . 119.2 no
C49 . C50 . C51 . 118.97(7) yes
C49 . C50 . H501 . 120.2 no
C51 . C50 . H501 . 120.9 no
C50 . C51 . C52 . 120.28(7) yes
C50 . C51 . O54 . 119.84(6) yes
C52 . C51 . O54 . 119.81(6) yes
C51 . C52 . C53 . 118.97(7) yes
C51 . C52 . H521 . 120.0 no
C53 . C52 . H521 . 121.0 no
C48 . C53 . C52 . 121.33(7) yes
C48 . C53 . H531 . 118.8 no
C52 . C53 . H531 . 119.8 no
C51 . O54 . C55 . 120.000(11) yes
O54 . C55 . H551 . 109.1 no
O54 . C55 . H552 . 109.9 no
H551 . C55 . H552 . 108.8 no
O54 . C55 . H553 . 110.9 no
H551 . C55 . H553 . 108.5 no
H552 . C55 . H553 . 109.6 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C20 . H501 . C25 . 121 1.18 1.98 2.782(11) yes
N7 . H71 . N3 2_656 159 0.95 1.95 2.853(11) yes
N7 . H71 . N33 2_656 144 0.95 2.11 2.937(11) yes
N37 . H71 . N3 2_656 140 1.15 1.95 2.919(11) yes
N37 . H71 . N33 2_656 125 1.15 2.11 2.924(11) yes
N7 . H371 . N3 2_656 121 1.12 2.11 2.853(11) yes
N7 . H371 . N33 2_656 137 1.12 2.02 2.937(11) yes
N37 . H371 . N3 2_656 142 0.95 2.11 2.919(11) yes
N37 . H371 . N33 2_656 157 0.95 2.02 2.924(11) yes




#==============================================================================
# start Validation Reply Form
#==============================================================================
_vrf_DIFMX01_Structure-2oa       
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*0.75
RESPONSE: The residual electron density is close to the heaviest atom 
(sulphur) and is thought to be the result of inadequacies in modelling 
the disorder.  See _refine_special_details section for more details.
;
_vrf_DIFMX02_Structure-2oa       
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*0.75
RESPONSE: The residual electron density is close to the heaviest atom 
(sulphur) and is thought to be the result of inadequacies in modelling 
the disorder.  See _refine_special_details section for more details.
;
_vrf_RFACR01_Structure-2oa       
;
PROBLEM: The value of the weighted R factor is > 0.25
RESPONSE: The high R-indices are thought to be the result of inadequacies 
in modelling the complex whole molecule disorder.  See _refine_special_details 
section for more details.
;
_vrf_PLAT084_Structure-2oa       
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.26 Report
RESPONSE: The high R-indices are thought to be the result of inadequacies 
in modelling the complex whole molecule disorder.  See _refine_special_details 
section for more details.
;
_vrf_PLAT088_Structure-2oa       
;
PROBLEM: Poor Data / Parameter Ratio ....................       8.61 Note  
RESPONSE: The poor data to parameter ratio is due to the whole molecule 
disorder which introduces twice as many atoms as would normally be expected 
for this type of structure.  Restraints and constraints were included to
counter the correlation effects; see _refine_special_details section for 
more details.
;
_vrf_PLAT097_Structure-2oa       
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.22 eA-3  
RESPONSE: The residual electron density is close to the heaviest atom 
(sulphur) and is thought to be the result of inadequacies in modelling 
the disorder.  See _refine_special_details section for more details.
;
_vrf_PLAT250_Structure-2oa       
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.2 Note  
RESPONSE: The structure appears to exhibit whole molecule disorder.  Despite
considerable efforts to model it it appears that the ADPs retain 
directionality. See _refine_special_details section for more details.
;
_vrf_PLAT331_Structure-2oa       
;
PROBLEM: Small Average Phenyl   C-C Dist. C8     -C13           1.37 Ang.
RESPONSE: The structure appears to exhibit whole molecule disorder; the slightly
short average phenyl bond distance is probably a function of inadequacies in the
model.  See _refine_special_details section for more details.
;
#==============================================================================
# end Validation Reply Form
#==============================================================================
