# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_pyn1816SNQ
_database_code_depnum_ccdc_archive 'CCDC 1904599'
loop_
_audit_author_name
_audit_author_address
'Anthony Willis'
;Australian National University
Australia
;
_audit_update_record             
;
2019-03-21 deposited with the CCDC.	2019-04-30 downloaded from the CCDC.
;
_audit_creation_date             18-09-03
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 'Z:\pyn1816SNQ\Tony_pyn1816SNQ_da At 12:23 on'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   6.8449(1)
_cell_length_b                   13.5001(1)
_cell_length_c                   29.2689(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2704.65(5)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

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 = C28 H40 F1 N1 O3 S1 
# Dc =      1.20 Fooo =   1056.00 Mu =     13.45 M =    489.69
# Found Formula = C28 H40 F1 N1 O3 S1 
# Dc =      1.20 FOOO =   1056.00 Mu =     13.45 M =    489.69

_chemical_formula_sum            'C28 H40 F N O3 S'
_chemical_formula_moiety         'C28 H40 F N O3 S'
_chemical_compound_source        ' from U of Wollongong '
_chemical_formula_weight         489.69


_cell_measurement_reflns_used    20466
_cell_measurement_theta_min      4
_cell_measurement_theta_max      74
_cell_measurement_temperature    150

_exptl_crystal_description       lath
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.021
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_max          0.419

_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1056
_exptl_absorpt_coefficient_mu    1.345

# Sheldrick geometric approximatio 0.91 0.97 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.51
_exptl_absorpt_correction_T_max  0.97
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
#_diffrn_ambient_temperature 150.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_measurement_method       'ω scans'


# If a reference occurs more than once, delete the author 
# and date from subsequent references. 

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'

_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            52258
_reflns_number_total             5480
_diffrn_reflns_av_R_equivalents  0.076
_diffrn_reflns_av_sigmaI/netI    0.0863

# Number of reflections without Friedels Law is 5480 
# Number of reflections with Friedels Law is 3146 
# Theoretical number of reflections is about 2738 


_diffrn_reflns_theta_min         3.606
_diffrn_reflns_theta_max         73.824
_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        73.824
_diffrn_measured_fraction_theta_full 0.999


_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_reflns_limit_h_min              -8
_reflns_limit_h_max              8
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              36

_oxford_diffrn_Wilson_B_factor   2.50
_oxford_diffrn_Wilson_scale      0.04

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

_refine_diff_density_min         -0.30
_refine_diff_density_max         0.36


# 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>-10.0\s(I)
_refine_ls_number_reflns         5480
_refine_ls_number_restraints     3
_refine_ls_number_parameters     308
_oxford_refine_ls_R_factor_ref   0.0439
_refine_ls_wR_factor_ref         0.1133
_refine_ls_goodness_of_fit_ref   0.9997
_refine_ls_shift/su_max          0.0233459
_refine_ls_shift/su_mean         0.0051833


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5480
_refine_ls_R_factor_all          0.0439
_refine_ls_wR_factor_all         0.1133

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                5261
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_gt          0.1113

_refine_ls_abs_structure_Flack   -0.025(14)
_refine_ls_abs_structure_details 'Flack (1983), 2334 Friedel-pairs'
# 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 ad


_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) + ( 0.09P)² + 0.17P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_special_details          
# see also _refine_ls_hydrogen for refinement keywords.                         
;                                                                               

Hydrogen atoms were 
observed in a difference electron density map.
and were included at calculated positions.
The H atoms were initially refined with soft restraints on the 
bond lengths and angles to regularise their geometry 
(C---H in the range 0.93--0.98Å\) and with
Uiso(H) in the range 1.2-1.5 times Ueq of the parent atom. 
and finally refined with riding constraints.



The largest peaks in the final difference electron density map 
were located near the S atom and between bonded atoms.
;

# 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 0.73616(6) 0.59471(3) 0.650549(13) 0.0270 1.0000 Uani . . . . . .
F1 F 0.48264(19) 0.68743(8) 0.50228(4) 0.0370 1.0000 Uani . . . . . .
O1 O 0.88186(19) 0.64815(12) 0.62563(5) 0.0378 1.0000 Uani . . . . . .
O2 O 0.7779(2) 0.49572(10) 0.66477(5) 0.0397 1.0000 Uani . . . . . .
O3 O 0.6305(3) 0.50532(11) 0.76477(6) 0.0459 1.0000 Uani . . . . . .
N1 N 0.5414(2) 0.59017(11) 0.61857(4) 0.0236 1.0000 Uani . . . . . .
C1 C 0.3142(3) 0.82679(14) 0.66153(7) 0.0366 1.0000 Uani . . . . . .
C2 C 0.3059(3) 0.77690(13) 0.62831(7) 0.0308 1.0000 Uani . . . . . .
C3 C 0.3108(3) 0.71699(13) 0.58674(6) 0.0296 1.0000 Uani . . . . . .
C4 C 0.5091(2) 0.66344(11) 0.58199(5) 0.0236 1.0000 Uani . . . . . .
C5 C 0.5340(2) 0.61470(12) 0.53479(6) 0.0255 1.0000 Uani . . . . . .
C6 C 0.7414(3) 0.58412(13) 0.52491(6) 0.0295 1.0000 Uani . . . . . .
C7 C 0.7696(3) 0.53414(13) 0.47864(6) 0.0314 1.0000 Uani . . . . . .
C8 C 0.9866(3) 0.52400(16) 0.46654(7) 0.0378 1.0000 Uani . . . . . .
C9 C 1.0198(3) 0.47763(15) 0.41961(7) 0.0388 1.0000 Uani . . . . . .
C10 C 1.2368(4) 0.47312(18) 0.40595(8) 0.0509 1.0000 Uani . . . . . .
C11 C 1.3240(4) 0.5733(2) 0.39588(10) 0.0590 1.0000 Uani . . . . . .
C12 C 0.3814(3) 0.52462(12) 0.63410(6) 0.0269 1.0000 Uani . . . . . .
C13 C 0.3425(3) 0.43786(12) 0.60264(6) 0.0278 1.0000 Uani . . . . . .
C14 C 0.4953(3) 0.37954(13) 0.58634(7) 0.0355 1.0000 Uani . . . . . .
C15 C 0.4577(4) 0.29811(15) 0.55925(8) 0.0466 1.0000 Uani . . . . . .
C16 C 0.2677(5) 0.27335(15) 0.54805(8) 0.0536 1.0000 Uani . . . . . .
C17 C 0.1155(4) 0.32974(18) 0.56443(10) 0.0558 1.0000 Uani . . . . . .
C18 C 0.1530(3) 0.41284(15) 0.59180(8) 0.0400 1.0000 Uani . . . . . .
C19 C 0.6727(3) 0.66619(13) 0.70015(6) 0.0273 1.0000 Uani . . . . . .
C20 C 0.8110(2) 0.65221(13) 0.74018(6) 0.0269 1.0000 Uani . . . . . .
C21 C 0.7509(3) 0.56834(14) 0.77200(6) 0.0346 1.0000 Uani . . . . . .
C22 C 0.8638(4) 0.5843(2) 0.81622(8) 0.0499 1.0000 Uani . . . . . .
C23 C 0.9696(3) 0.68228(19) 0.80684(7) 0.0435 1.0000 Uani . . . . . .
C24 C 1.1388(3) 0.6596(2) 0.77427(8) 0.0474 1.0000 Uani . . . . . .
C25 C 1.0310(3) 0.63253(16) 0.72939(7) 0.0355 1.0000 Uani . . . . . .
C26 C 0.8237(3) 0.73901(15) 0.77548(7) 0.0356 1.0000 Uani . . . . . .
C27 C 0.6282(3) 0.7624(2) 0.79850(8) 0.0503 1.0000 Uani . . . . . .
C28 C 0.9056(4) 0.83510(17) 0.75580(10) 0.0512 1.0000 Uani . . . . . .
H11 H 0.3262 0.8677 0.6875 0.0438 1.0000 Uiso R . . . . .
H31 H 0.2017 0.6691 0.5866 0.0354 1.0000 Uiso R . . . . .
H32 H 0.2949 0.7609 0.5603 0.0340 1.0000 Uiso R . . . . .
H41 H 0.6127 0.7138 0.5857 0.0282 1.0000 Uiso R . . . . .
H51 H 0.4409 0.5590 0.5312 0.0310 1.0000 Uiso R . . . . .
H61 H 0.8232 0.6421 0.5266 0.0355 1.0000 Uiso R . . . . .
H62 H 0.7804 0.5377 0.5487 0.0350 1.0000 Uiso R . . . . .
H71 H 0.7035 0.5746 0.4561 0.0378 1.0000 Uiso R . . . . .
H72 H 0.7070 0.4692 0.4801 0.0390 1.0000 Uiso R . . . . .
H81 H 1.0515 0.5891 0.4666 0.0447 1.0000 Uiso R . . . . .
H82 H 1.0458 0.4822 0.4887 0.0459 1.0000 Uiso R . . . . .
H91 H 0.9507 0.5161 0.3969 0.0467 1.0000 Uiso R . . . . .
H92 H 0.9623 0.4110 0.4197 0.0466 1.0000 Uiso R . . . . .
H101 H 1.3212 0.4330 0.4284 0.0597 1.0000 Uiso R . . . . .
H102 H 1.2463 0.4344 0.3785 0.0614 1.0000 Uiso R . . . . .
H111 H 1.4632 0.5683 0.3873 0.0880 1.0000 Uiso R . . . . .
H112 H 1.3121 0.6162 0.4234 0.0872 1.0000 Uiso R . . . . .
H113 H 1.2458 0.6074 0.3719 0.0882 1.0000 Uiso R . . . . .
H121 H 0.4208 0.4986 0.6641 0.0320 1.0000 Uiso R . . . . .
H122 H 0.2612 0.5631 0.6364 0.0320 1.0000 Uiso R . . . . .
H141 H 0.6270 0.3931 0.5940 0.0430 1.0000 Uiso R . . . . .
H151 H 0.5609 0.2592 0.5485 0.0558 1.0000 Uiso R . . . . .
H161 H 0.2451 0.2192 0.5289 0.0640 1.0000 Uiso R . . . . .
H171 H -0.0104 0.3126 0.5570 0.0672 1.0000 Uiso R . . . . .
H181 H 0.0467 0.4516 0.6029 0.0483 1.0000 Uiso R . . . . .
H191 H 0.6719 0.7345 0.6902 0.0336 1.0000 Uiso R . . . . .
H192 H 0.5383 0.6452 0.7090 0.0324 1.0000 Uiso R . . . . .
H221 H 0.7747 0.5884 0.8424 0.0597 1.0000 Uiso R . . . . .
H222 H 0.9542 0.5293 0.8228 0.0603 1.0000 Uiso R . . . . .
H231 H 1.0040 0.7219 0.8345 0.0520 1.0000 Uiso R . . . . .
H241 H 1.2223 0.7170 0.7692 0.0573 1.0000 Uiso R . . . . .
H242 H 1.2152 0.6038 0.7857 0.0567 1.0000 Uiso R . . . . .
H251 H 1.0731 0.6744 0.7046 0.0432 1.0000 Uiso R . . . . .
H252 H 1.0528 0.5630 0.7205 0.0436 1.0000 Uiso R . . . . .
H271 H 0.6481 0.8032 0.8250 0.0749 1.0000 Uiso R . . . . .
H272 H 0.5560 0.7053 0.8079 0.0738 1.0000 Uiso R . . . . .
H273 H 0.5456 0.7983 0.7776 0.0746 1.0000 Uiso R . . . . .
H281 H 0.9477 0.8774 0.7806 0.0770 1.0000 Uiso R . . . . .
H282 H 1.0138 0.8230 0.7360 0.0768 1.0000 Uiso R . . . . .
H283 H 0.8039 0.8699 0.7397 0.0762 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          5.25(10)
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 . O1 . 1.4308(15) yes
S1 . O2 . 1.4285(14) yes
S1 . N1 . 1.6300(14) yes
S1 . C19 . 1.7966(17) yes
F1 . C5 . 1.4117(18) yes
O3 . C21 . 1.203(3) yes
N1 . C4 . 1.474(2) yes
N1 . C12 . 1.480(2) yes
C1 . C2 . 1.184(3) yes
C1 . H11 . 0.943 no
C2 . C3 . 1.461(3) yes
C3 . C4 . 1.544(2) yes
C3 . H31 . 0.988 no
C3 . H32 . 0.982 no
C4 . C5 . 1.540(2) yes
C4 . H41 . 0.988 no
C5 . C6 . 1.507(2) yes
C5 . H51 . 0.991 no
C6 . C7 . 1.525(2) yes
C6 . H61 . 0.963 no
C6 . H62 . 0.974 no
C7 . C8 . 1.533(3) yes
C7 . H71 . 0.969 no
C7 . H72 . 0.976 no
C8 . C9 . 1.526(3) yes
C8 . H81 . 0.985 no
C8 . H82 . 0.951 no
C9 . C10 . 1.540(3) yes
C9 . H91 . 0.967 no
C9 . H92 . 0.981 no
C10 . C11 . 1.507(4) yes
C10 . H101 . 1.029 no
C10 . H102 . 0.959 no
C11 . H111 . 0.988 no
C11 . H112 . 0.995 no
C11 . H113 . 0.996 no
C12 . C13 . 1.514(2) yes
C12 . H121 . 0.984 no
C12 . H122 . 0.975 no
C13 . C14 . 1.393(3) yes
C13 . C18 . 1.377(3) yes
C14 . C15 . 1.380(3) yes
C14 . H141 . 0.947 no
C15 . C16 . 1.382(4) yes
C15 . H151 . 0.934 no
C16 . C17 . 1.377(4) yes
C16 . H161 . 0.935 no
C17 . C18 . 1.402(3) yes
C17 . H171 . 0.919 no
C18 . H181 . 0.954 no
C19 . C20 . 1.518(2) yes
C19 . H191 . 0.967 no
C19 . H192 . 0.998 no
C20 . C21 . 1.523(2) yes
C20 . C25 . 1.561(2) yes
C20 . C26 . 1.565(2) yes
C21 . C22 . 1.523(3) yes
C22 . C23 . 1.533(3) yes
C22 . H221 . 0.980 no
C22 . H222 . 0.986 no
C23 . C24 . 1.531(3) yes
C23 . C26 . 1.558(3) yes
C23 . H231 . 1.000 no
C24 . C25 . 1.550(3) yes
C24 . H241 . 0.975 no
C24 . H242 . 0.975 no
C25 . H251 . 0.965 no
C25 . H252 . 0.985 no
C26 . C27 . 1.531(3) yes
C26 . C28 . 1.526(3) yes
C27 . H271 . 0.960 no
C27 . H272 . 0.956 no
C27 . H273 . 0.963 no
C28 . H281 . 0.966 no
C28 . H282 . 0.954 no
C28 . H283 . 0.963 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
O1 . S1 . O2 . 118.73(10) yes
O1 . S1 . N1 . 107.23(8) yes
O2 . S1 . N1 . 107.20(8) yes
O1 . S1 . C19 . 108.04(9) yes
O2 . S1 . C19 . 108.39(8) yes
N1 . S1 . C19 . 106.66(7) yes
S1 . N1 . C4 . 120.95(11) yes
S1 . N1 . C12 . 116.83(11) yes
C4 . N1 . C12 . 120.89(13) yes
C2 . C1 . H11 . 177.4 no
C1 . C2 . C3 . 175.8(2) yes
C2 . C3 . C4 . 110.76(15) yes
C2 . C3 . H31 . 110.4 no
C4 . C3 . H31 . 111.0 no
C2 . C3 . H32 . 108.7 no
C4 . C3 . H32 . 108.0 no
H31 . C3 . H32 . 107.9 no
C3 . C4 . N1 . 112.37(13) yes
C3 . C4 . C5 . 112.20(14) yes
N1 . C4 . C5 . 110.38(12) yes
C3 . C4 . H41 . 107.4 no
N1 . C4 . H41 . 105.9 no
C5 . C4 . H41 . 108.3 no
C4 . C5 . F1 . 106.27(12) yes
C4 . C5 . C6 . 113.16(14) yes
F1 . C5 . C6 . 107.20(13) yes
C4 . C5 . H51 . 110.5 no
F1 . C5 . H51 . 107.2 no
C6 . C5 . H51 . 112.1 no
C5 . C6 . C7 . 114.25(15) yes
C5 . C6 . H61 . 108.4 no
C7 . C6 . H61 . 109.4 no
C5 . C6 . H62 . 107.3 no
C7 . C6 . H62 . 108.4 no
H61 . C6 . H62 . 109.1 no
C6 . C7 . C8 . 111.54(16) yes
C6 . C7 . H71 . 107.3 no
C8 . C7 . H71 . 110.2 no
C6 . C7 . H72 . 107.6 no
C8 . C7 . H72 . 110.8 no
H71 . C7 . H72 . 109.3 no
C7 . C8 . C9 . 112.88(18) yes
C7 . C8 . H81 . 110.9 no
C9 . C8 . H81 . 107.5 no
C7 . C8 . H82 . 108.0 no
C9 . C8 . H82 . 107.9 no
H81 . C8 . H82 . 109.6 no
C8 . C9 . C10 . 113.18(19) yes
C8 . C9 . H91 . 109.0 no
C10 . C9 . H91 . 108.3 no
C8 . C9 . H92 . 108.3 no
C10 . C9 . H92 . 110.5 no
H91 . C9 . H92 . 107.4 no
C9 . C10 . C11 . 113.43(19) yes
C9 . C10 . H101 . 113.4 no
C11 . C10 . H101 . 112.0 no
C9 . C10 . H102 . 107.7 no
C11 . C10 . H102 . 107.3 no
H101 . C10 . H102 . 102.1 no
C10 . C11 . H111 . 111.7 no
C10 . C11 . H112 . 109.4 no
H111 . C11 . H112 . 108.9 no
C10 . C11 . H113 . 109.8 no
H111 . C11 . H113 . 111.8 no
H112 . C11 . H113 . 105.0 no
N1 . C12 . C13 . 113.94(13) yes
N1 . C12 . H121 . 106.6 no
C13 . C12 . H121 . 108.3 no
N1 . C12 . H122 . 109.1 no
C13 . C12 . H122 . 107.8 no
H121 . C12 . H122 . 111.1 no
C12 . C13 . C14 . 120.93(17) yes
C12 . C13 . C18 . 119.69(16) yes
C14 . C13 . C18 . 119.30(17) yes
C13 . C14 . C15 . 120.5(2) yes
C13 . C14 . H141 . 121.7 no
C15 . C14 . H141 . 117.8 no
C14 . C15 . C16 . 120.3(2) yes
C14 . C15 . H151 . 120.0 no
C16 . C15 . H151 . 119.7 no
C15 . C16 . C17 . 119.7(2) yes
C15 . C16 . H161 . 119.2 no
C17 . C16 . H161 . 121.1 no
C16 . C17 . C18 . 120.2(2) yes
C16 . C17 . H171 . 119.2 no
C18 . C17 . H171 . 120.6 no
C17 . C18 . C13 . 120.0(2) yes
C17 . C18 . H181 . 119.6 no
C13 . C18 . H181 . 120.4 no
S1 . C19 . C20 . 113.96(12) yes
S1 . C19 . H191 . 105.6 no
C20 . C19 . H191 . 110.8 no
S1 . C19 . H192 . 106.3 no
C20 . C19 . H192 . 109.8 no
H191 . C19 . H192 . 110.2 no
C19 . C20 . C21 . 113.31(15) yes
C19 . C20 . C25 . 117.81(15) yes
C21 . C20 . C25 . 104.95(15) yes
C19 . C20 . C26 . 116.81(15) yes
C21 . C20 . C26 . 99.66(15) yes
C25 . C20 . C26 . 101.99(14) yes
C20 . C21 . O3 . 127.12(17) yes
C20 . C21 . C22 . 106.11(16) yes
O3 . C21 . C22 . 126.66(18) yes
C21 . C22 . C23 . 102.11(16) yes
C21 . C22 . H221 . 110.9 no
C23 . C22 . H221 . 112.7 no
C21 . C22 . H222 . 112.2 no
C23 . C22 . H222 . 112.8 no
H221 . C22 . H222 . 106.3 no
C22 . C23 . C24 . 107.2(2) yes
C22 . C23 . C26 . 103.08(16) yes
C24 . C23 . C26 . 102.52(17) yes
C22 . C23 . H231 . 115.3 no
C24 . C23 . H231 . 115.7 no
C26 . C23 . H231 . 111.5 no
C23 . C24 . C25 . 102.41(16) yes
C23 . C24 . H241 . 112.3 no
C25 . C24 . H241 . 109.7 no
C23 . C24 . H242 . 110.3 no
C25 . C24 . H242 . 111.3 no
H241 . C24 . H242 . 110.6 no
C24 . C25 . C20 . 104.33(16) yes
C24 . C25 . H251 . 111.0 no
C20 . C25 . H251 . 109.9 no
C24 . C25 . H252 . 112.1 no
C20 . C25 . H252 . 111.2 no
H251 . C25 . H252 . 108.4 no
C23 . C26 . C20 . 93.23(16) yes
C23 . C26 . C27 . 113.76(19) yes
C20 . C26 . C27 . 113.41(15) yes
C23 . C26 . C28 . 113.86(18) yes
C20 . C26 . C28 . 114.05(17) yes
C27 . C26 . C28 . 108.1(2) yes
C26 . C27 . H271 . 110.5 no
C26 . C27 . H272 . 114.3 no
H271 . C27 . H272 . 107.7 no
C26 . C27 . H273 . 109.7 no
H271 . C27 . H273 . 107.9 no
H272 . C27 . H273 . 106.5 no
C26 . C28 . H281 . 109.2 no
C26 . C28 . H282 . 111.6 no
H281 . C28 . H282 . 108.9 no
C26 . C28 . H283 . 109.5 no
H281 . C28 . H283 . 107.1 no
H282 . C28 . H283 . 110.4 no


loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 N1 C4 -22.55(14) . . . . no
O1 S1 N1 C12 170.44(12) . . . . no
O2 S1 N1 C4 -151.09(12) . . . . no
O2 S1 N1 C12 41.90(14) . . . . no
C19 S1 N1 C4 92.99(13) . . . . no
C19 S1 N1 C12 -74.02(13) . . . . no
O1 S1 C19 C20 -83.11(14) . . . . no
O2 S1 C19 C20 46.77(15) . . . . no
N1 S1 C19 C20 161.89(12) . . . . no
S1 N1 C4 C3 -124.91(13) . . . . no
S1 N1 C4 C5 108.99(12) . . . . no
C12 N1 C4 C3 41.58(19) . . . . no
C12 N1 C4 C5 -84.52(16) . . . . no
S1 N1 C12 C13 -114.56(15) . . . . no
C4 N1 C12 C13 78.41(19) . . . . no
C2 C3 C4 N1 65.06(18) . . . . no
C2 C3 C4 C5 -169.85(14) . . . . no
N1 C4 C5 F1 174.61(11) . . . . no
N1 C4 C5 C6 -67.99(16) . . . . no
C3 C4 C5 F1 48.43(16) . . . . no
C3 C4 C5 C6 165.83(14) . . . . no
F1 C5 C6 C7 -64.07(18) . . . . no
C4 C5 C6 C7 179.09(14) . . . . no
C5 C6 C7 C8 168.49(15) . . . . no
C6 C7 C8 C9 -177.91(16) . . . . no
C7 C8 C9 C10 176.43(17) . . . . no
C8 C9 C10 C11 -69.9(3) . . . . no
N1 C12 C13 C14 47.3(2) . . . . no
N1 C12 C13 C18 -136.08(18) . . . . no
C12 C13 C14 C15 177.24(18) . . . . no
C18 C13 C14 C15 0.6(3) . . . . no
C12 C13 C18 C17 -177.0(2) . . . . no
C14 C13 C18 C17 -0.3(3) . . . . no
C13 C14 C15 C16 -0.1(3) . . . . no
C14 C15 C16 C17 -0.7(3) . . . . no
C15 C16 C17 C18 1.0(4) . . . . no
C16 C17 C18 C13 -0.5(4) . . . . no
S1 C19 C20 C21 -89.95(16) . . . . no
S1 C19 C20 C25 33.1(2) . . . . no
S1 C19 C20 C26 155.02(13) . . . . no
C19 C20 C21 O3 12.9(3) . . . . no
C19 C20 C21 C22 -163.30(17) . . . . no
C25 C20 C21 O3 -117.0(2) . . . . no
C25 C20 C21 C22 66.85(19) . . . . no
C26 C20 C21 O3 137.8(2) . . . . no
C26 C20 C21 C22 -38.42(19) . . . . no
C19 C20 C25 C24 160.13(17) . . . . no
C21 C20 C25 C24 -72.71(19) . . . . no
C26 C20 C25 C24 30.8(2) . . . . no
C19 C20 C26 C23 177.59(15) . . . . no
C19 C20 C26 C27 60.0(2) . . . . no
C19 C20 C26 C28 -64.4(2) . . . . no
C21 C20 C26 C23 55.16(15) . . . . no
C21 C20 C26 C27 -62.45(19) . . . . no
C21 C20 C26 C28 173.15(18) . . . . no
C25 C20 C26 C23 -52.50(16) . . . . no
C25 C20 C26 C27 -170.12(17) . . . . no
C25 C20 C26 C28 65.5(2) . . . . no
O3 C21 C22 C23 -172.2(2) . . . . no
C20 C21 C22 C23 4.0(2) . . . . no
C21 C22 C23 C24 -75.4(2) . . . . no
C21 C22 C23 C26 32.4(2) . . . . no
C22 C23 C24 C25 68.6(2) . . . . no
C26 C23 C24 C25 -39.6(2) . . . . no
C22 C23 C26 C20 -54.32(18) . . . . no
C22 C23 C26 C27 63.0(2) . . . . no
C22 C23 C26 C28 -172.47(19) . . . . no
C24 C23 C26 C20 56.98(19) . . . . no
C24 C23 C26 C27 174.28(19) . . . . no
C24 C23 C26 C28 -61.2(2) . . . . no
C23 C24 C25 C20 5.0(2) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
S1 C6 3.6803(18) . . no
O1 C2 3.384(2) . 1_655 no
O1 C3 3.283(2) . 1_655 no
O1 C6 3.219(2) . . no
O1 C25 3.211(3) . . no
O2 C21 3.293(2) . . no
O2 C25 3.161(3) . . no
O2 O3 3.099(2) . . no
O2 C14 3.387(2) . . no
O3 C1 3.257(3) . 3_646 no
C1 C19 3.464(3) . . no
C2 C19 3.600(3) . . no
C2 C12 3.449(2) . . no
C5 C14 3.525(2) . . no
C5 C13 3.371(2) . . no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 03/09/18 at 12:51:27
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   1,X'S) H   (  11,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) H   (  32,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) H   (  62,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'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   (  10,X'S) H   ( 101,X'S) H   ( 102,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) H   ( 113,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,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   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 222,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) H   ( 242,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) H   ( 252,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) H   ( 272,X'S) H   ( 273,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) H   ( 282,X'S) H   ( 283,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 03/09/18 at 12:51:27
#
#LIST     16                                                                    
LIMIT  F(1,U[23]) 
LIMIT  C(14,U[23]) 
LIMIT  C(15,U[23]) 
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;


#===END


####################################################################### 
# 
# 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_pyn1821SNMQ
_database_code_depnum_ccdc_archive 'CCDC 1904600'
loop_
_audit_author_name
_audit_author_address
'Anthony Willis'
;Australian National University
Australia
;
_audit_update_record             
;
2019-03-21 deposited with the CCDC.	2019-04-30 downloaded from the CCDC.
;
_audit_creation_date             18-10-29
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 'Z:\pyn1821SNMQ\Tony_pyn1821SNMQ_ At 12: 4 on'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   8.0413(3)
_cell_length_b                   11.5956(3)
_cell_length_c                   10.5319(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.192(4)
_cell_angle_gamma                90
_cell_volume                     909.29(6)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1 '
_symmetry_space_group_name_Hall  'P 2yb'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-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 0.0033 0.0016 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 0.0171 0.0103 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 0.0061 0.0033 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 0.0106 0.0060 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 0.1246 0.1234 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 = C20 H22 F1 N1 O2 S1 
# Dc =      1.31 Fooo =    380.00 Mu =      2.01 M =    359.46
# Found Formula = C20 H22 F1 N1 O2 S1 
# Dc =      1.31 FOOO =    380.00 Mu =      2.01 M =    359.46

_chemical_formula_sum            'C20 H22 F N O2 S'
_chemical_formula_moiety         'C20 H22 F1 N1 O2 S1'
_chemical_compound_source        ' from U of Wollongong '
_chemical_formula_weight         359.46


_cell_measurement_reflns_used    10321
_cell_measurement_theta_min      4
_cell_measurement_theta_max      29
_cell_measurement_temperature    150

_exptl_crystal_description       lath
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.105
_exptl_crystal_size_mid          0.251
_exptl_crystal_size_max          0.570

_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             380
_exptl_absorpt_coefficient_mu    0.201

# Sheldrick geometric approximatio 0.95 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.98
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
#_diffrn_ambient_temperature 150.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_source         
'SuperMova (Mo) X-ray Source' ################
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_measurement_method       'ω scans'


# If a reference occurs more than once, delete the author 
# and date from subsequent references. 

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'

_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            15813
_reflns_number_total             4405
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_av_sigmaI/netI    0.0350
# Number of reflections without Friedels Law is 4405 
# Number of reflections with Friedels Law is 2419 
# Theoretical number of reflections is about 2505 


_diffrn_reflns_theta_min         3.514
_diffrn_reflns_theta_max         29.377
_diffrn_measured_fraction_theta_max 0.919

_diffrn_reflns_theta_full        27.345
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_reflns_limit_h_min              -10
_reflns_limit_h_max              10
_reflns_limit_k_min              -14
_reflns_limit_k_max              15
_reflns_limit_l_min              0
_reflns_limit_l_max              14

_oxford_diffrn_Wilson_B_factor   2.27
_oxford_diffrn_Wilson_scale      0.01

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

_refine_diff_density_min         -0.27
_refine_diff_density_max         0.19


# 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>-10.0\s(I)
_refine_ls_number_reflns         4405
_refine_ls_number_restraints     1
_refine_ls_number_parameters     227
_oxford_refine_ls_R_factor_ref   0.0308
_refine_ls_wR_factor_ref         0.0735
_refine_ls_goodness_of_fit_ref   1.0017
_refine_ls_shift/su_max          0.0005528
_refine_ls_shift/su_mean         0.0001139


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4405
_refine_ls_R_factor_all          0.0308
_refine_ls_wR_factor_all         0.0735

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4253
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_gt          0.0723

_refine_ls_abs_structure_Flack   -0.03(5)
_refine_ls_abs_structure_details 'Flack (1983), 1986 Friedel-pairs'
# 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 ad


_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 + 0.20P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_special_details          
# see also _refine_ls_hydrogen for refinement keywords.                         
;                                                                               

Hydrogen atoms were 
observed in a difference electron density map.
and were included at calculated positions.
The H atoms were initially refined with soft restraints on the 
bond lengths and angles to regularise their geometry 
(C---H in the range 0.93--0.98Å\) and with
Uiso(H) in the range 1.2-1.5 times Ueq of the parent atom. 
and finally refined with riding constraints.



The largest peaks in the final difference electron density map 
were located near the S atom and between bonded atoms.
;

# 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 0.54345(4) 0.33157(7) 0.53630(3) 0.0267 1.0000 Uani . . . . . .
F1 F 0.85777(14) 0.35543(10) 0.22630(10) 0.0444 1.0000 Uani . . . . . .
O1 O 0.43962(14) 0.26661(12) 0.41718(11) 0.0374 1.0000 Uani . . . . . .
O2 O 0.45639(14) 0.41236(11) 0.59299(12) 0.0361 1.0000 Uani . . . . . .
N1 N 0.68933(16) 0.40459(12) 0.49703(12) 0.0281 1.0000 Uani . . . . . .
C1 C 0.7759(2) 0.50575(15) 0.57853(17) 0.0365 1.0000 Uani . . . . . .
C2 C 0.9758(2) 0.49667(18) 0.63860(17) 0.0434 1.0000 Uani . . . . . .
C3 C 1.0650(2) 0.4099(2) 0.61330(18) 0.0470 1.0000 Uani . . . . . .
C4 C 0.9773(2) 0.31437(17) 0.51838(18) 0.0419 1.0000 Uani . . . . . .
C5 C 0.7873(2) 0.34600(14) 0.42196(15) 0.0307 1.0000 Uani . . . . . .
C6 C 0.7892(2) 0.42386(15) 0.30510(15) 0.0311 1.0000 Uani . . . . . .
C7 C 0.6071(2) 0.46925(15) 0.21376(16) 0.0350 1.0000 Uani . . . . . .
C8 C 0.61750(19) 0.54849(15) 0.10378(15) 0.0294 1.0000 Uani . . . . . .
C9 C 0.7070(2) 0.65264(15) 0.13921(16) 0.0347 1.0000 Uani . . . . . .
C10 C 0.7255(3) 0.72499(16) 0.0413(2) 0.0439 1.0000 Uani . . . . . .
C11 C 0.6503(3) 0.69423(17) -0.09514(19) 0.0470 1.0000 Uani . . . . . .
C12 C 0.5562(3) 0.59293(18) -0.13226(17) 0.0455 1.0000 Uani . . . . . .
C13 C 0.5396(2) 0.51975(16) -0.03380(16) 0.0364 1.0000 Uani . . . . . .
C14 C 0.65979(18) 0.23270(13) 0.66543(14) 0.0249 1.0000 Uani . . . . . .
C15 C 0.7127(2) 0.26485(14) 0.80241(15) 0.0315 1.0000 Uani . . . . . .
C16 C 0.8072(2) 0.18666(15) 0.90253(16) 0.0348 1.0000 Uani . . . . . .
C17 C 0.8509(2) 0.07777(14) 0.86940(16) 0.0315 1.0000 Uani . . . . . .
C18 C 0.7954(2) 0.04795(14) 0.73225(16) 0.0305 1.0000 Uani . . . . . .
C19 C 0.69950(19) 0.12369(14) 0.62986(15) 0.0281 1.0000 Uani . . . . . .
C20 C 0.9557(2) -0.00627(17) 0.97887(19) 0.0445 1.0000 Uani . . . . . .
H11 H 0.7323 0.5146 0.6506 0.0451 1.0000 Uiso R . . . . .
H12 H 0.7383 0.5754 0.5200 0.0426 1.0000 Uiso R . . . . .
H21 H 1.0386 0.5561 0.6979 0.0510 1.0000 Uiso R . . . . .
H31 H 1.1906 0.4096 0.6530 0.0570 1.0000 Uiso R . . . . .
H41 H 1.0484 0.2955 0.4670 0.0491 1.0000 Uiso R . . . . .
H42 H 0.9730 0.2484 0.5723 0.0508 1.0000 Uiso R . . . . .
H51 H 0.7210 0.2761 0.3804 0.0352 1.0000 Uiso R . . . . .
H61 H 0.8747 0.4910 0.3427 0.0347 1.0000 Uiso R . . . . .
H71 H 0.5564 0.5092 0.2705 0.0426 1.0000 Uiso R . . . . .
H72 H 0.5280 0.4043 0.1716 0.0426 1.0000 Uiso R . . . . .
H91 H 0.7554 0.6757 0.2319 0.0420 1.0000 Uiso R . . . . .
H101 H 0.7895 0.7931 0.0674 0.0522 1.0000 Uiso R . . . . .
H111 H 0.6627 0.7426 -0.1635 0.0566 1.0000 Uiso R . . . . .
H121 H 0.5035 0.5719 -0.2259 0.0548 1.0000 Uiso R . . . . .
H131 H 0.4732 0.4501 -0.0621 0.0438 1.0000 Uiso R . . . . .
H151 H 0.6845 0.3363 0.8261 0.0385 1.0000 Uiso R . . . . .
H161 H 0.8472 0.2075 0.9965 0.0411 1.0000 Uiso R . . . . .
H181 H 0.8190 -0.0274 0.7067 0.0364 1.0000 Uiso R . . . . .
H191 H 0.6635 0.1037 0.5353 0.0334 1.0000 Uiso R . . . . .
H201 H 0.9486 -0.0846 0.9411 0.0666 1.0000 Uiso R . . . . .
H202 H 1.0783 0.0168 1.0225 0.0688 1.0000 Uiso R . . . . .
H203 H 0.9028 -0.0083 1.0466 0.0677 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          9.4(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 . O1 . 1.4308(12) yes
S1 . O2 . 1.4283(11) yes
S1 . N1 . 1.6218(12) yes
S1 . C14 . 1.7545(14) yes
F1 . C6 . 1.4027(17) yes
N1 . C1 . 1.465(2) yes
N1 . C5 . 1.4756(18) yes
C1 . C2 . 1.493(2) yes
C1 . H11 . 0.954 no
C1 . H12 . 0.992 no
C2 . C3 . 1.320(3) yes
C2 . H21 . 0.938 no
C3 . C4 . 1.480(3) yes
C3 . H31 . 0.936 no
C4 . C5 . 1.526(2) yes
C4 . H41 . 0.949 no
C4 . H42 . 0.961 no
C5 . C6 . 1.531(2) yes
C5 . H51 . 0.977 no
C6 . C7 . 1.511(2) yes
C6 . H61 . 1.015 no
C7 . C8 . 1.505(2) yes
C7 . H71 . 0.961 no
C7 . H72 . 0.978 no
C8 . C9 . 1.383(2) yes
C8 . C13 . 1.385(2) yes
C9 . C10 . 1.380(2) yes
C9 . H91 . 0.943 no
C10 . C11 . 1.379(3) yes
C10 . H101 . 0.926 no
C11 . C12 . 1.372(3) yes
C11 . H111 . 0.947 no
C12 . C13 . 1.385(2) yes
C12 . H121 . 0.947 no
C13 . H131 . 0.952 no
C14 . C15 . 1.392(2) yes
C14 . C19 . 1.389(2) yes
C15 . C16 . 1.381(2) yes
C15 . H151 . 0.919 no
C16 . C17 . 1.390(2) yes
C16 . H161 . 0.949 no
C17 . C18 . 1.385(2) yes
C17 . C20 . 1.502(2) yes
C18 . C19 . 1.379(2) yes
C18 . H181 . 0.954 no
C19 . H191 . 0.955 no
C20 . H201 . 0.984 no
C20 . H202 . 0.955 no
C20 . H203 . 0.959 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
O1 . S1 . O2 . 119.74(7) yes
O1 . S1 . N1 . 106.86(7) yes
O2 . S1 . N1 . 106.27(6) yes
O1 . S1 . C14 . 107.42(7) yes
O2 . S1 . C14 . 107.85(7) yes
N1 . S1 . C14 . 108.27(7) yes
S1 . N1 . C1 . 119.87(10) yes
S1 . N1 . C5 . 118.69(10) yes
C1 . N1 . C5 . 116.80(12) yes
N1 . C1 . C2 . 112.91(15) yes
N1 . C1 . H11 . 108.4 no
C2 . C1 . H11 . 109.3 no
N1 . C1 . H12 . 108.8 no
C2 . C1 . H12 . 110.3 no
H11 . C1 . H12 . 106.9 no
C1 . C2 . C3 . 123.27(17) yes
C1 . C2 . H21 . 116.9 no
C3 . C2 . H21 . 119.8 no
C2 . C3 . C4 . 123.40(15) yes
C2 . C3 . H31 . 119.3 no
C4 . C3 . H31 . 117.2 no
C3 . C4 . C5 . 111.79(14) yes
C3 . C4 . H41 . 108.8 no
C5 . C4 . H41 . 110.1 no
C3 . C4 . H42 . 108.1 no
C5 . C4 . H42 . 109.5 no
H41 . C4 . H42 . 108.5 no
C4 . C5 . N1 . 110.93(13) yes
C4 . C5 . C6 . 111.39(12) yes
N1 . C5 . C6 . 109.20(12) yes
C4 . C5 . H51 . 109.8 no
N1 . C5 . H51 . 108.1 no
C6 . C5 . H51 . 107.4 no
C5 . C6 . F1 . 105.53(12) yes
C5 . C6 . C7 . 114.54(12) yes
F1 . C6 . C7 . 108.86(12) yes
C5 . C6 . H61 . 110.4 no
F1 . C6 . H61 . 107.8 no
C7 . C6 . H61 . 109.4 no
C6 . C7 . C8 . 112.37(13) yes
C6 . C7 . H71 . 108.0 no
C8 . C7 . H71 . 110.2 no
C6 . C7 . H72 . 109.2 no
C8 . C7 . H72 . 109.7 no
H71 . C7 . H72 . 107.3 no
C7 . C8 . C9 . 119.99(14) yes
C7 . C8 . C13 . 121.57(15) yes
C9 . C8 . C13 . 118.44(15) yes
C8 . C9 . C10 . 121.42(15) yes
C8 . C9 . H91 . 119.8 no
C10 . C9 . H91 . 118.8 no
C9 . C10 . C11 . 119.52(18) yes
C9 . C10 . H101 . 120.1 no
C11 . C10 . H101 . 120.4 no
C10 . C11 . C12 . 119.73(16) yes
C10 . C11 . H111 . 120.6 no
C12 . C11 . H111 . 119.7 no
C11 . C12 . C13 . 120.67(16) yes
C11 . C12 . H121 . 120.0 no
C13 . C12 . H121 . 119.4 no
C12 . C13 . C8 . 120.17(16) yes
C12 . C13 . H131 . 119.1 no
C8 . C13 . H131 . 120.7 no
S1 . C14 . C15 . 119.55(11) yes
S1 . C14 . C19 . 119.67(11) yes
C15 . C14 . C19 . 120.78(13) yes
C14 . C15 . C16 . 118.70(14) yes
C14 . C15 . H151 . 120.9 no
C16 . C15 . H151 . 120.4 no
C15 . C16 . C17 . 121.55(14) yes
C15 . C16 . H161 . 120.1 no
C17 . C16 . H161 . 118.3 no
C16 . C17 . C18 . 118.44(14) yes
C16 . C17 . C20 . 121.23(15) yes
C18 . C17 . C20 . 120.33(15) yes
C17 . C18 . C19 . 121.43(14) yes
C17 . C18 . H181 . 120.2 no
C19 . C18 . H181 . 118.4 no
C14 . C19 . C18 . 119.09(13) yes
C14 . C19 . H191 . 119.5 no
C18 . C19 . H191 . 121.4 no
C17 . C20 . H201 . 111.0 no
C17 . C20 . H202 . 111.4 no
H201 . C20 . H202 . 110.2 no
C17 . C20 . H203 . 108.0 no
H201 . C20 . H203 . 107.7 no
H202 . C20 . H203 . 108.5 no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 N1 C1 160.38(12) . . . . no
O1 S1 N1 C5 -44.52(13) . . . . no
O2 S1 N1 C1 31.45(14) . . . . no
O2 S1 N1 C5 -173.45(11) . . . . no
C14 S1 N1 C1 -84.19(13) . . . . no
C14 S1 N1 C5 70.92(12) . . . . no
O1 S1 C14 C15 -154.76(13) . . . . no
O1 S1 C14 C19 25.83(15) . . . . no
O2 S1 C14 C15 -24.43(16) . . . . no
O2 S1 C14 C19 156.17(13) . . . . no
N1 S1 C14 C15 90.17(14) . . . . no
N1 S1 C14 C19 -89.23(14) . . . . no
S1 N1 C1 C2 122.42(14) . . . . no
C5 N1 C1 C2 -33.15(19) . . . . no
S1 N1 C5 C4 -102.13(14) . . . . no
S1 N1 C5 C6 134.71(11) . . . . no
C1 N1 C5 C4 53.73(18) . . . . no
C1 N1 C5 C6 -69.43(16) . . . . no
N1 C1 C2 C3 4.2(2) . . . . no
C1 C2 C3 C4 2.5(3) . . . . no
C2 C3 C4 C5 18.1(3) . . . . no
C3 C4 C5 N1 -43.95(19) . . . . no
C3 C4 C5 C6 77.92(18) . . . . no
N1 C5 C6 F1 -170.69(12) . . . . no
N1 C5 C6 C7 -50.96(18) . . . . no
C4 C5 C6 F1 66.45(16) . . . . no
C4 C5 C6 C7 -173.83(14) . . . . no
F1 C6 C7 C8 -64.16(18) . . . . no
C5 C6 C7 C8 178.00(13) . . . . no
C6 C7 C8 C9 -65.0(2) . . . . no
C6 C7 C8 C13 114.75(18) . . . . no
C7 C8 C9 C10 177.22(18) . . . . no
C13 C8 C9 C10 -2.6(3) . . . . no
C7 C8 C13 C12 -178.04(18) . . . . no
C9 C8 C13 C12 1.7(3) . . . . no
C8 C9 C10 C11 1.3(3) . . . . no
C9 C10 C11 C12 0.8(4) . . . . no
C10 C11 C12 C13 -1.6(4) . . . . no
C11 C12 C13 C8 0.3(3) . . . . no
S1 C14 C15 C16 -178.74(13) . . . . no
C19 C14 C15 C16 0.7(2) . . . . no
S1 C14 C19 C18 178.19(13) . . . . no
C15 C14 C19 C18 -1.2(2) . . . . no
C14 C15 C16 C17 0.4(3) . . . . no
C15 C16 C17 C18 -0.8(3) . . . . no
C15 C16 C17 C20 179.24(16) . . . . no
C16 C17 C18 C19 0.2(3) . . . . no
C20 C17 C18 C19 -179.81(16) . . . . no
C17 C18 C19 C14 0.8(3) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 C11 3.298(2) . 2_645 no
O2 C12 3.413(2) . 1_556 no
O2 C19 3.296(2) . 2_656 no
O2 C3 3.234(2) . 1_455 no
C1 C7 3.584(2) . . no
C2 C6 3.365(2) . . no
C4 C14 3.578(2) . . no



_iucr_refine_instruction_details_constraints 
;
#
# Punched on 29/10/18 at 15:25:59
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   1,X'S) H   (  11,X'S) H   (  12,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) H   (  42,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,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   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) H   ( 203,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 29/10/18 at 15:25:59
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
#===END

