# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_11-300K
_database_code_depnum_ccdc_archive 'CCDC 2074459'
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2021-03-31 deposited with the CCDC.	2021-04-27 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2019-11-26
_audit_creation_method           'CRYSTALS_ver_14.61_build_7356 '

_oxford_structure_analysis_title '7248 or 7246 Andie 300K'
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   6.2560(3)
_cell_length_b                   7.6732(3)
_cell_length_c                   28.1296(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1350.32(9)

_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,z+1/2
x+1/2,-y+1/2,-z
-x,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'
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 = C16 H14 O2 S1 
# Dc =      1.33 Fooo =    568.00 Mu =     20.81 M =    270.35
# Found Formula = C16 H14 O2 S1 
# Dc =      1.33 FOOO =    568.00 Mu =     20.81 M =    270.35

_chemical_formula_sum            'C16 H14 O2 S'
_chemical_formula_moiety         'C16 H14 O2 S'
_chemical_compound_source        .
_chemical_formula_weight         270.35


_cell_measurement_reflns_used    2206
_cell_measurement_theta_min      3.16
_cell_measurement_theta_max      76.82
_cell_measurement_temperature    300

_exptl_crystal_description       plate
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.08
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_max          0.14

_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    2.081

# Sheldrick geometric approximatio 0.81 0.85 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  0.85
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_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 (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_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      300
_diffrn_reflns_number            4335
_diffrn_reflns_av_unetI/netI     0.029
_reflns_number_total             2516
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_av_sigmaI/netI    0.0294
# Number of reflections without Friedels Law is 2516 
# Number of reflections with Friedels Law is 1669 
# Theoretical number of reflections is about 1429 

_diffrn_reflns_theta_min         3.142
_diffrn_reflns_theta_max         77.094
_diffrn_measured_fraction_theta_max 0.988

_diffrn_reflns_theta_full        74.781
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       25
_reflns_limit_h_min              -7
_reflns_limit_h_max              7
_reflns_limit_k_min              0
_reflns_limit_k_max              9
_reflns_limit_l_min              0
_reflns_limit_l_max              35

_oxford_diffrn_Wilson_B_factor   5.15
_oxford_diffrn_Wilson_scale      0.03

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

_refine_diff_density_min         -0.13
_refine_diff_density_max         0.13


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

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2515
_oxford_refine_ls_R_factor_ref   0.0388
_refine_ls_wR_factor_ref         0.0943
_refine_ls_goodness_of_fit_ref   1.0021
_refine_ls_shift/su_max          0.0009521
_refine_ls_shift/su_mean         0.0000540


# Computed with no filters except I/sigma = -10 
_oxford_reflns_number_all        2516
_refine_ls_R_factor_all          0.0389
_refine_ls_wR_factor_all         0.0947

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2252
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_gt          0.0884

# For an explanation, see Cooper & Watkin, Acta Cryst. (2016). B72, 661-683 
_oxford_Hooft_y                  -0.037(10) # for 813 Friedel pairs 
_oxford_Bijvoet_difference       -0.032(12) # for 813 Friedel pairs 
# (Similar to the Parsons(q).) 
_oxford_refined_Flack_x          -0.02(2) # for 847 Friedel pairs 
_refine_ls_abs_structure_Flack   -0.032(12)
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 813 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) + ( 0.05P)² + 0.09P] 
 ,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
C1 C 0.6095(5) 0.6321(4) 0.27277(9) 0.0833 1.0000 Uani . . . . . .
C2 C 0.5755(6) 0.6175(5) 0.22398(11) 0.1092 1.0000 Uani . . . . . .
C3 C 0.7282(8) 0.5455(4) 0.19574(9) 0.1163 1.0000 Uani . . . . . .
C4 C 0.9191(7) 0.4921(4) 0.21390(10) 0.1080 1.0000 Uani . . . . . .
C5 C 0.9581(5) 0.5075(4) 0.26231(9) 0.0846 1.0000 Uani . . . . . .
C6 C 0.8012(4) 0.5768(3) 0.29094(7) 0.0625 1.0000 Uani . . . . . .
S7 S 0.84612(10) 0.59323(8) 0.352723(18) 0.0659 1.0000 Uani . . . . . .
O8 O 0.7268(3) 0.7397(2) 0.36981(6) 0.0853 1.0000 Uani . . . . . .
O9 O 1.0723(3) 0.5882(3) 0.36100(6) 0.0908 1.0000 Uani . . . . . .
C10 C 0.7349(4) 0.4059(3) 0.37486(7) 0.0697 1.0000 Uani . . . . . .
C11 C 0.5161(4) 0.3765(4) 0.39444(8) 0.0774 1.0000 Uani . . . . . .
C12 C 0.7033(4) 0.3552(3) 0.42663(8) 0.0653 1.0000 Uani . . . . . .
C13 C 0.8427(6) 0.2471(3) 0.39489(8) 0.0818 1.0000 Uani . . . . . .
C14 C 0.7480(4) 0.4449(3) 0.47175(7) 0.0596 1.0000 Uani . . . . . .
C15 C 0.9513(4) 0.4465(4) 0.49098(9) 0.0802 1.0000 Uani . . . . . .
C16 C 0.9871(5) 0.5302(4) 0.53401(10) 0.0944 1.0000 Uani . . . . . .
C17 C 0.8237(5) 0.6089(3) 0.55822(8) 0.0852 1.0000 Uani . . . . . .
C18 C 0.6234(5) 0.6054(4) 0.53947(9) 0.0871 1.0000 Uani . . . . . .
C19 C 0.5852(4) 0.5233(4) 0.49636(9) 0.0787 1.0000 Uani . . . . . .
H11 H 0.5056 0.6706 0.2917 0.0999 1.0000 Uiso R . . . . .
H21 H 0.4484 0.6570 0.2114 0.1310 1.0000 Uiso R . . . . .
H31 H 0.7039 0.5329 0.1629 0.1401 1.0000 Uiso R . . . . .
H41 H 1.0268 0.4492 0.1940 0.1303 1.0000 Uiso R . . . . .
H51 H 1.0902 0.4733 0.2753 0.1025 1.0000 Uiso R . . . . .
H111 H 0.4251 0.4758 0.3996 0.0935 1.0000 Uiso R . . . . .
H112 H 0.4397 0.2742 0.3854 0.0938 1.0000 Uiso R . . . . .
H131 H 0.9971 0.2501 0.4006 0.0982 1.0000 Uiso R . . . . .
H132 H 0.7948 0.1334 0.3850 0.0972 1.0000 Uiso R . . . . .
H151 H 1.0653 0.3885 0.4746 0.0961 1.0000 Uiso R . . . . .
H161 H 1.1248 0.5332 0.5474 0.1134 1.0000 Uiso R . . . . .
H171 H 0.8456 0.6646 0.5878 0.1018 1.0000 Uiso R . . . . .
H181 H 0.5167 0.6593 0.5545 0.1053 1.0000 Uiso R . . . . .
H191 H 0.4467 0.5214 0.4834 0.0939 1.0000 Uiso R . . . . .

_refine_ls_extinction_coef       20(4)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          6.53(18)
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
C1 . C2 . 1.394(4) yes
C1 . C6 . 1.371(3) yes
C1 . H11 . 0.890 no
C2 . C3 . 1.360(5) yes
C2 . H21 . 0.922 no
C3 . C4 . 1.362(5) yes
C3 . H31 . 0.942 no
C4 . C5 . 1.389(4) yes
C4 . H41 . 0.937 no
C5 . C6 . 1.376(3) yes
C5 . H51 . 0.941 no
C6 . S7 . 1.7651(19) yes
S7 . O8 . 1.4320(18) yes
S7 . O9 . 1.4344(17) yes
S7 . C10 . 1.714(3) yes
C10 . C11 . 1.492(3) yes
C10 . C12 . 1.520(3) yes
C10 . C13 . 1.503(4) yes
C11 . C12 . 1.489(3) yes
C11 . H111 . 0.962 no
C11 . H112 . 0.954 no
C12 . C13 . 1.499(3) yes
C12 . C14 . 1.471(3) yes
C13 . H131 . 0.979 no
C13 . H132 . 0.963 no
C14 . C15 . 1.382(3) yes
C14 . C19 . 1.371(3) yes
C15 . C16 . 1.388(4) yes
C15 . H151 . 0.959 no
C16 . C17 . 1.369(4) yes
C16 . H161 . 0.941 no
C17 . C18 . 1.360(4) yes
C17 . H171 . 0.946 no
C18 . C19 . 1.387(4) yes
C18 . H181 . 0.892 no
C19 . H191 . 0.940 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 . C1 . C6 . 118.4(3) yes
C2 . C1 . H11 . 120.2 no
C6 . C1 . H11 . 121.3 no
C1 . C2 . C3 . 120.0(3) yes
C1 . C2 . H21 . 119.0 no
C3 . C2 . H21 . 121.0 no
C2 . C3 . C4 . 121.3(3) yes
C2 . C3 . H31 . 120.1 no
C4 . C3 . H31 . 118.6 no
C3 . C4 . C5 . 119.8(3) yes
C3 . C4 . H41 . 120.8 no
C5 . C4 . H41 . 119.4 no
C4 . C5 . C6 . 118.8(3) yes
C4 . C5 . H51 . 120.8 no
C6 . C5 . H51 . 120.4 no
C5 . C6 . C1 . 121.7(2) yes
C5 . C6 . S7 . 119.36(19) yes
C1 . C6 . S7 . 118.95(18) yes
C6 . S7 . O8 . 107.67(11) yes
C6 . S7 . O9 . 108.35(11) yes
O8 . S7 . O9 . 118.74(13) yes
C6 . S7 . C10 . 103.48(10) yes
O8 . S7 . C10 . 108.94(12) yes
O9 . S7 . C10 . 108.60(13) yes
S7 . C10 . C11 . 129.3(2) yes
S7 . C10 . C12 . 127.96(18) yes
C11 . C10 . C12 . 59.24(15) yes
S7 . C10 . C13 . 129.3(2) yes
C11 . C10 . C13 . 98.7(2) yes
C12 . C10 . C13 . 59.46(15) yes
C10 . C11 . C12 . 61.31(15) yes
C10 . C11 . H111 . 118.6 no
C12 . C11 . H111 . 117.5 no
C10 . C11 . H112 . 119.0 no
C12 . C11 . H112 . 117.8 no
H111 . C11 . H112 . 113.3 no
C10 . C12 . C11 . 59.45(15) yes
C10 . C12 . C13 . 59.69(15) yes
C11 . C12 . C13 . 99.0(2) yes
C10 . C12 . C14 . 133.0(2) yes
C11 . C12 . C14 . 128.5(2) yes
C13 . C12 . C14 . 131.5(2) yes
C10 . C13 . C12 . 60.85(16) yes
C10 . C13 . H131 . 119.0 no
C12 . C13 . H131 . 117.5 no
C10 . C13 . H132 . 119.0 no
C12 . C13 . H132 . 119.5 no
H131 . C13 . H132 . 112.1 no
C12 . C14 . C15 . 121.2(2) yes
C12 . C14 . C19 . 120.0(2) yes
C15 . C14 . C19 . 118.8(2) yes
C14 . C15 . C16 . 119.6(3) yes
C14 . C15 . H151 . 119.6 no
C16 . C15 . H151 . 120.8 no
C15 . C16 . C17 . 121.1(3) yes
C15 . C16 . H161 . 120.6 no
C17 . C16 . H161 . 118.2 no
C16 . C17 . C18 . 119.1(2) yes
C16 . C17 . H171 . 121.9 no
C18 . C17 . H171 . 118.9 no
C17 . C18 . C19 . 120.4(3) yes
C17 . C18 . H181 . 119.7 no
C19 . C18 . H181 . 119.8 no
C18 . C19 . C14 . 120.9(3) yes
C18 . C19 . H191 . 120.3 no
C14 . C19 . H191 . 118.8 no

####################################################################### 
# 
# 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_16
_database_code_depnum_ccdc_archive 'CCDC 2074462'
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2021-03-31 deposited with the CCDC.	2021-04-27 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2020-03-16
_audit_creation_method           'CRYSTALS_ver_14.61_build_7453 '

_oxford_structure_analysis_title 7305
_chemical_name_systematic        .
_chemical_melting_point          'not measured'


_cell_length_a                   7.5201(2)
_cell_length_b                   6.1363(2)
_cell_length_c                   29.1109(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.778(2)
_cell_angle_gamma                90
_cell_volume                     1340.42(7)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P c '
_symmetry_space_group_name_Hall  'P -2yc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x,-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'
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 = C16 H13 F1 O2 S1 
# Dc =      1.43 Fooo =    600.00 Mu =     22.45 M =    288.34
# Found Formula = C16 H13 F1 O2 S1 
# Dc =      1.43 FOOO =    600.00 Mu =     22.45 M =    288.34

_chemical_formula_sum            'C16 H13 F O2 S'
_chemical_formula_moiety         'C16 H13 F O2 S'
_chemical_compound_source        .
_chemical_formula_weight         288.34


_cell_measurement_reflns_used    5640
_cell_measurement_theta_min      5.87
_cell_measurement_theta_max      76.93
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.05
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_max          0.20

_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    2.245

# Sheldrick geometric approximatio 0.80 0.89 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.89
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_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 (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_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            11889
_diffrn_reflns_av_unetI/netI     0.050
_reflns_number_total             3740
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_av_sigmaI/netI    0.0507
# Number of reflections without Friedels Law is 3740 
# Number of reflections with Friedels Law is 2824 
# Theoretical number of reflections is about 2838 

_diffrn_reflns_theta_min         3.043
_diffrn_reflns_theta_max         77.111
_diffrn_measured_fraction_theta_max 0.989

_diffrn_reflns_theta_full        75.569
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       33
_reflns_limit_h_min              -7
_reflns_limit_h_max              9
_reflns_limit_k_min              0
_reflns_limit_k_max              7
_reflns_limit_l_min              -36
_reflns_limit_l_max              33

_oxford_diffrn_Wilson_B_factor   2.42
_oxford_diffrn_Wilson_scale      0.02

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

_refine_diff_density_min         -0.21
_refine_diff_density_max         0.18


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

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_restraints     2
_refine_ls_number_parameters     362
_refine_ls_number_reflns         3738
_oxford_refine_ls_R_factor_ref   0.0318
_refine_ls_R_factor_all          0.0318
_refine_ls_wR_factor_ref         0.0754 #Calculated the Oxford way
_refine_ls_wR_factor_all         0.0754
_refine_ls_goodness_of_fit_ref   1.0019
_refine_ls_shift/su_max          0.0003583
_refine_ls_shift/su_mean         0.0000466


# Computed with no filters except I/sigma = -10 
_oxford_reflns_number_all        3738
_oxford_refine_ls_R_factor_all   0.0318
_oxford_refine_ls_wR_factor_all  0.0754

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3539
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_gt          0.0734

# For an explanation, see Cooper & Watkin, Acta Cryst. (2016). B72, 661-683 
_oxford_Hooft_y                  -0.013(14) # for 758 Friedel pairs 
_oxford_Bijvoet_difference       0.008(14) # for 758 Friedel pairs 
# (Similar to the Parsons(q).) 
_oxford_refined_Flack_x          0.009(19) # for 916 Friedel pairs 
_refine_ls_abs_structure_Flack   0.008(14)
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 758 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 + 0.14P] 
 ,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
C1 C 0.4982(3) 0.2825(4) 0.71671(10) 0.0353 1.0000 Uani . . . . . .
C2 C 0.4639(4) 0.2545(5) 0.66968(10) 0.0401 1.0000 Uani . . . . . .
C3 C 0.4915(3) 0.4243(5) 0.63962(9) 0.0401 1.0000 Uani . . . . . .
C4 C 0.5554(3) 0.6242(5) 0.65624(9) 0.0392 1.0000 Uani . . . . . .
C5 C 0.5879(3) 0.6553(4) 0.70314(9) 0.0344 1.0000 Uani . . . . . .
C6 C 0.5572(3) 0.4839(4) 0.73297(8) 0.0289 1.0000 Uani . . . . . .
S7 S 0.58059(11) 0.52892(9) 0.79330(4) 0.0287 1.0000 Uani . . . . . .
O8 O 0.4484(3) 0.6862(4) 0.80488(7) 0.0422 1.0000 Uani . . . . . .
O9 O 0.5832(3) 0.3203(3) 0.81603(7) 0.0384 1.0000 Uani . . . . . .
C10 C 0.7868(3) 0.6489(4) 0.80266(9) 0.0321 1.0000 Uani . . . . . .
C11 C 0.8250(4) 0.8824(5) 0.81499(10) 0.0424 1.0000 Uani . . . . . .
C12 C 0.8627(3) 0.7107(4) 0.85070(9) 0.0320 1.0000 Uani . . . . . .
C13 C 0.9569(3) 0.5480(5) 0.82276(9) 0.0374 1.0000 Uani . . . . . .
C14 C 0.7932(3) 0.6890(4) 0.89632(8) 0.0281 1.0000 Uani . . . . . .
C15 C 0.6972(3) 0.8580(4) 0.91513(9) 0.0330 1.0000 Uani . . . . . .
C16 C 0.6386(3) 0.8413(4) 0.9590(1) 0.0365 1.0000 Uani . . . . . .
C17 C 0.6760(3) 0.6535(5) 0.98370(9) 0.0369 1.0000 Uani . . . . . .
C18 C 0.7712(4) 0.4836(5) 0.96675(9) 0.0375 1.0000 Uani . . . . . .
C19 C 0.8305(3) 0.5021(4) 0.92281(9) 0.0324 1.0000 Uani . . . . . .
F20 F 0.6163(2) 0.6350(3) 1.02649(6) 0.0499 1.0000 Uani . . . . . .
C51 C 0.1716(3) 1.0499(4) 0.45243(9) 0.0332 1.0000 Uani . . . . . .
C52 C 0.2067(4) 1.0039(5) 0.40745(10) 0.0400 1.0000 Uani . . . . . .
C53 C 0.2795(3) 0.8055(5) 0.39575(9) 0.0385 1.0000 Uani . . . . . .
C54 C 0.3189(3) 0.6501(5) 0.42955(10) 0.0378 1.0000 Uani . . . . . .
C55 C 0.2867(3) 0.6931(4) 0.47517(9) 0.0332 1.0000 Uani . . . . . .
C56 C 0.2148(3) 0.8929(4) 0.48614(8) 0.0281 1.0000 Uani . . . . . .
S57 S 0.18827(11) 0.95852(9) 0.54450(4) 0.0295 1.0000 Uani . . . . . .
O58 O 0.3373(2) 0.8666(4) 0.57137(7) 0.0411 1.0000 Uani . . . . . .
O59 O 0.1533(3) 1.1887(3) 0.54760(8) 0.0438 1.0000 Uani . . . . . .
C60 C -0.0014(3) 0.8199(4) 0.55849(9) 0.0299 1.0000 Uani . . . . . .
C61 C -0.0119(3) 0.6112(4) 0.58478(9) 0.0336 1.0000 Uani . . . . . .
C62 C -0.0713(3) 0.8168(4) 0.60639(8) 0.0292 1.0000 Uani . . . . . .
C63 C -0.1820(3) 0.9110(5) 0.56648(9) 0.0365 1.0000 Uani . . . . . .
C64 C -0.0078(3) 0.9206(4) 0.65013(8) 0.0265 1.0000 Uani . . . . . .
C65 C 0.1061(3) 0.8088(4) 0.68163(8) 0.0283 1.0000 Uani . . . . . .
C66 C 0.1627(3) 0.9026(4) 0.72339(8) 0.0331 1.0000 Uani . . . . . .
C67 C 0.1017(3) 1.1084(4) 0.73288(9) 0.0352 1.0000 Uani . . . . . .
C68 C -0.0117(4) 1.2235(4) 0.70330(10) 0.0374 1.0000 Uani . . . . . .
C69 C -0.0679(3) 1.1279(4) 0.66140(9) 0.0334 1.0000 Uani . . . . . .
F70 F 0.1589(2) 1.2014(3) 0.77380(7) 0.0496 1.0000 Uani . . . . . .
H11 H 0.4822 0.1682 0.7372 0.0424 1.0000 Uiso R . . . . .
H21 H 0.4252 0.1218 0.6580 0.0484 1.0000 Uiso R . . . . .
H31 H 0.4679 0.4039 0.6083 0.0471 1.0000 Uiso R . . . . .
H41 H 0.5735 0.7361 0.6351 0.0466 1.0000 Uiso R . . . . .
H51 H 0.6295 0.7895 0.7146 0.0410 1.0000 Uiso R . . . . .
H111 H 0.7220 0.9769 0.8178 0.0508 1.0000 Uiso R . . . . .
H112 H 0.9250 0.9568 0.8018 0.0513 1.0000 Uiso R . . . . .
H132 H 0.9575 0.3966 0.8320 0.0451 1.0000 Uiso R . . . . .
H131 H 1.0682 0.5852 0.8093 0.0445 1.0000 Uiso R . . . . .
H151 H 0.6717 0.9835 0.8979 0.0404 1.0000 Uiso R . . . . .
H161 H 0.5746 0.9508 0.9716 0.0442 1.0000 Uiso R . . . . .
H181 H 0.7946 0.3576 0.9847 0.0438 1.0000 Uiso R . . . . .
H191 H 0.8965 0.3899 0.9108 0.0387 1.0000 Uiso R . . . . .
H511 H 0.1227 1.1827 0.4611 0.0394 1.0000 Uiso R . . . . .
H521 H 0.1820 1.1109 0.3847 0.0484 1.0000 Uiso R . . . . .
H531 H 0.3009 0.7785 0.3649 0.0458 1.0000 Uiso R . . . . .
H541 H 0.3674 0.5168 0.4222 0.0453 1.0000 Uiso R . . . . .
H551 H 0.3146 0.5942 0.4981 0.0404 1.0000 Uiso R . . . . .
H611 H 0.1001 0.5407 0.5974 0.0403 1.0000 Uiso R . . . . .
H612 H -0.1006 0.5030 0.5735 0.0404 1.0000 Uiso R . . . . .
H632 H -0.2002 1.0699 0.5644 0.0441 1.0000 Uiso R . . . . .
H631 H -0.2850 0.8291 0.5535 0.0446 1.0000 Uiso R . . . . .
H651 H 0.1472 0.6673 0.6745 0.0340 1.0000 Uiso R . . . . .
H661 H 0.2421 0.8291 0.7441 0.0401 1.0000 Uiso R . . . . .
H681 H -0.0494 1.3624 0.7112 0.0460 1.0000 Uiso R . . . . .
H691 H -0.1462 1.2024 0.6411 0.0408 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          6.76(12)
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
C1 . C2 . 1.387(3) yes
C1 . C6 . 1.386(3) yes
C1 . H11 . 0.934 no
C2 . C3 . 1.385(4) yes
C2 . H21 . 0.922 no
C3 . C4 . 1.392(4) yes
C3 . H31 . 0.925 no
C4 . C5 . 1.384(3) yes
C4 . H41 . 0.937 no
C5 . C6 . 1.393(3) yes
C5 . H51 . 0.935 no
C6 . S7 . 1.775(2) yes
S7 . O8 . 1.441(2) yes
S7 . O9 . 1.4404(19) yes
S7 . C10 . 1.722(3) yes
C10 . C11 . 1.501(3) yes
C10 . C12 . 1.524(3) yes
C10 . C13 . 1.505(3) yes
C11 . C12 . 1.494(4) yes
C11 . H111 . 0.975 no
C11 . H112 . 0.980 no
C12 . C13 . 1.496(3) yes
C12 . C14 . 1.465(3) yes
C13 . H132 . 0.966 no
C13 . H131 . 0.974 no
C14 . C15 . 1.396(3) yes
C14 . C19 . 1.400(3) yes
C15 . C16 . 1.383(4) yes
C15 . H151 . 0.933 no
C16 . C17 . 1.377(4) yes
C16 . H161 . 0.917 no
C17 . C18 . 1.375(4) yes
C17 . F20 . 1.356(3) yes
C18 . C19 . 1.387(4) yes
C18 . H181 . 0.944 no
C19 . H191 . 0.930 no
C51 . C52 . 1.382(4) yes
C51 . C56 . 1.398(3) yes
C51 . H511 . 0.935 no
C52 . C53 . 1.387(4) yes
C52 . H521 . 0.942 no
C53 . C54 . 1.388(4) yes
C53 . H531 . 0.936 no
C54 . C55 . 1.391(3) yes
C54 . H541 . 0.926 no
C55 . C56 . 1.385(3) yes
C55 . H551 . 0.916 no
C56 . S57 . 1.770(2) yes
S57 . O58 . 1.4391(19) yes
S57 . O59 . 1.4405(19) yes
S57 . C60 . 1.732(3) yes
C60 . C61 . 1.497(3) yes
C60 . C62 . 1.522(3) yes
C60 . C63 . 1.501(3) yes
C61 . C62 . 1.491(3) yes
C61 . H611 . 0.996 no
C61 . H612 . 0.982 no
C62 . C63 . 1.500(3) yes
C62 . C64 . 1.475(3) yes
C63 . H632 . 0.985 no
C63 . H631 . 0.978 no
C64 . C65 . 1.393(3) yes
C64 . C69 . 1.396(3) yes
C65 . C66 . 1.387(3) yes
C65 . H651 . 0.949 no
C66 . C67 . 1.377(4) yes
C66 . H661 . 0.936 no
C67 . C68 . 1.368(4) yes
C67 . F70 . 1.365(3) yes
C68 . C69 . 1.394(4) yes
C68 . H681 . 0.932 no
C69 . H691 . 0.927 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 . C1 . C6 . 118.8(2) yes
C2 . C1 . H11 . 120.9 no
C6 . C1 . H11 . 120.2 no
C1 . C2 . C3 . 120.3(3) yes
C1 . C2 . H21 . 120.4 no
C3 . C2 . H21 . 119.3 no
C2 . C3 . C4 . 120.4(2) yes
C2 . C3 . H31 . 119.6 no
C4 . C3 . H31 . 120.0 no
C3 . C4 . C5 . 119.9(3) yes
C3 . C4 . H41 . 118.7 no
C5 . C4 . H41 . 121.4 no
C4 . C5 . C6 . 119.0(2) yes
C4 . C5 . H51 . 120.5 no
C6 . C5 . H51 . 120.5 no
C5 . C6 . C1 . 121.5(2) yes
C5 . C6 . S7 . 119.30(19) yes
C1 . C6 . S7 . 119.05(19) yes
C6 . S7 . O8 . 108.10(11) yes
C6 . S7 . O9 . 108.28(11) yes
O8 . S7 . O9 . 118.43(13) yes
C6 . S7 . C10 . 104.64(11) yes
O8 . S7 . C10 . 107.74(12) yes
O9 . S7 . C10 . 108.81(12) yes
S7 . C10 . C11 . 127.1(2) yes
S7 . C10 . C12 . 122.08(17) yes
C11 . C10 . C12 . 59.20(16) yes
S7 . C10 . C13 . 128.28(19) yes
C11 . C10 . C13 . 98.9(2) yes
C12 . C10 . C13 . 59.19(16) yes
C10 . C11 . C12 . 61.16(17) yes
C10 . C11 . H111 . 116.5 no
C12 . C11 . H111 . 118.4 no
C10 . C11 . H112 . 119.4 no
C12 . C11 . H112 . 119.1 no
H111 . C11 . H112 . 113.0 no
C10 . C12 . C11 . 59.64(17) yes
C10 . C12 . C13 . 59.78(16) yes
C11 . C12 . C13 . 99.6(2) yes
C10 . C12 . C14 . 132.4(2) yes
C11 . C12 . C14 . 129.2(2) yes
C13 . C12 . C14 . 130.0(2) yes
C10 . C13 . C12 . 61.03(16) yes
C10 . C13 . H132 . 119.4 no
C12 . C13 . H132 . 119.0 no
C10 . C13 . H131 . 118.6 no
C12 . C13 . H131 . 120.8 no
H132 . C13 . H131 . 110.4 no
C12 . C14 . C15 . 120.8(2) yes
C12 . C14 . C19 . 120.2(2) yes
C15 . C14 . C19 . 118.9(2) yes
C14 . C15 . C16 . 120.8(2) yes
C14 . C15 . H151 . 119.7 no
C16 . C15 . H151 . 119.5 no
C15 . C16 . C17 . 118.5(2) yes
C15 . C16 . H161 . 121.5 no
C17 . C16 . H161 . 120.0 no
C16 . C17 . C18 . 122.7(2) yes
C16 . C17 . F20 . 118.7(2) yes
C18 . C17 . F20 . 118.6(3) yes
C17 . C18 . C19 . 118.4(2) yes
C17 . C18 . H181 . 120.3 no
C19 . C18 . H181 . 121.3 no
C14 . C19 . C18 . 120.7(2) yes
C14 . C19 . H191 . 119.5 no
C18 . C19 . H191 . 119.8 no
C52 . C51 . C56 . 118.3(2) yes
C52 . C51 . H511 . 122.4 no
C56 . C51 . H511 . 119.2 no
C51 . C52 . C53 . 121.0(2) yes
C51 . C52 . H521 . 118.8 no
C53 . C52 . H521 . 120.2 no
C52 . C53 . C54 . 119.9(2) yes
C52 . C53 . H531 . 119.1 no
C54 . C53 . H531 . 121.0 no
C53 . C54 . C55 . 120.3(2) yes
C53 . C54 . H541 . 120.8 no
C55 . C54 . H541 . 118.9 no
C54 . C55 . C56 . 118.9(2) yes
C54 . C55 . H551 . 121.5 no
C56 . C55 . H551 . 119.5 no
C51 . C56 . C55 . 121.6(2) yes
C51 . C56 . S57 . 118.78(19) yes
C55 . C56 . S57 . 119.52(18) yes
C56 . S57 . O58 . 107.42(11) yes
C56 . S57 . O59 . 108.39(12) yes
O58 . S57 . O59 . 119.29(13) yes
C56 . S57 . C60 . 105.11(11) yes
O58 . S57 . C60 . 107.68(12) yes
O59 . S57 . C60 . 108.07(12) yes
S57 . C60 . C61 . 127.78(18) yes
S57 . C60 . C62 . 124.12(17) yes
C61 . C60 . C62 . 59.19(15) yes
S57 . C60 . C63 . 128.41(19) yes
C61 . C60 . C63 . 99.2(2) yes
C62 . C60 . C63 . 59.47(15) yes
C60 . C61 . C62 . 61.27(15) yes
C60 . C61 . H611 . 119.2 no
C62 . C61 . H611 . 118.7 no
C60 . C61 . H612 . 117.7 no
C62 . C61 . H612 . 119.9 no
H611 . C61 . H612 . 111.7 no
C60 . C62 . C61 . 59.55(15) yes
C60 . C62 . C63 . 59.56(15) yes
C61 . C62 . C63 . 99.5(2) yes
C60 . C62 . C64 . 132.3(2) yes
C61 . C62 . C64 . 129.8(2) yes
C63 . C62 . C64 . 129.3(2) yes
C60 . C63 . C62 . 60.97(15) yes
C60 . C63 . H632 . 118.8 no
C62 . C63 . H632 . 119.7 no
C60 . C63 . H631 . 116.8 no
C62 . C63 . H631 . 119.1 no
H632 . C63 . H631 . 112.5 no
C62 . C64 . C65 . 120.4(2) yes
C62 . C64 . C69 . 120.3(2) yes
C65 . C64 . C69 . 119.2(2) yes
C64 . C65 . C66 . 120.8(2) yes
C64 . C65 . H651 . 120.2 no
C66 . C65 . H651 . 119.0 no
C65 . C66 . C67 . 118.0(2) yes
C65 . C66 . H661 . 120.7 no
C67 . C66 . H661 . 121.3 no
C66 . C67 . C68 . 123.3(2) yes
C66 . C67 . F70 . 117.9(2) yes
C68 . C67 . F70 . 118.8(2) yes
C67 . C68 . C69 . 118.3(2) yes
C67 . C68 . H681 . 120.3 no
C69 . C68 . H681 . 121.4 no
C64 . C69 . C68 . 120.3(2) yes
C64 . C69 . H691 . 120.1 no
C68 . C69 . H691 . 119.6 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
C11 . H111 . O9 1_565 152 0.98 2.35 3.246(4) yes
C66 . H661 . O8 . 172 0.94 2.44 3.367(4) yes



# 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
3 1 33 x .
0 7 15 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_14
_database_code_depnum_ccdc_archive 'CCDC 2074461'
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2021-03-31 deposited with the CCDC.	2021-04-27 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2020-03-19
_audit_creation_method           'CRYSTALS_ver_14.61_build_7453 '

_oxford_structure_analysis_title 7307
_chemical_name_systematic        .
_chemical_melting_point          'not measured'


_cell_length_a                   7.22830(10)
_cell_length_b                   19.74990(10)
_cell_length_c                   21.88370(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.4390(5)
_cell_angle_gamma                90
_cell_volume                     3123.99(5)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-x,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'
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            8

# Given Formula = C18 H16 O4 S1 
# Dc =      1.40 Fooo =   1376.00 Mu =     20.01 M =    328.39
# Found Formula = C18 H16 O4 S1 
# Dc =      1.40 FOOO =   1376.00 Mu =     20.01 M =    328.39

_chemical_formula_sum            'C18 H16 O4 S'
_chemical_formula_moiety         'C18 H16 O4 S'
_chemical_compound_source        .
_chemical_formula_weight         328.39


_cell_measurement_reflns_used    48133
_cell_measurement_theta_min      3.98
_cell_measurement_theta_max      76.17
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_max          0.20

_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1376
_exptl_absorpt_coefficient_mu    2.001

# Sheldrick geometric approximatio 0.70 0.82 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_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  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_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 (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_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            86693
_diffrn_reflns_av_unetI/netI     0.032
_reflns_number_total             6514
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_av_sigmaI/netI    0.0318
# Number of reflections with Friedels Law is 6514 
# Theoretical number of reflections is about 13129 

_diffrn_reflns_theta_min         4.040
_diffrn_reflns_theta_max         76.500
_diffrn_measured_fraction_theta_max 0.995

_diffrn_reflns_theta_full        76.500
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              0
_reflns_limit_k_max              24
_reflns_limit_l_min              0
_reflns_limit_l_max              27

_oxford_diffrn_Wilson_B_factor   1.87
_oxford_diffrn_Wilson_scale      0.18

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

_refine_diff_density_min         -0.37
_refine_diff_density_max         0.30


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

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     416
_refine_ls_number_reflns         6513
_oxford_refine_ls_R_factor_ref   0.0298
_refine_ls_R_factor_all          0.0298
_refine_ls_wR_factor_ref         0.0832 #Calculated the Oxford way
_refine_ls_wR_factor_all         0.0832
_refine_ls_goodness_of_fit_ref   0.9991
_refine_ls_shift/su_max          0.0012062
_refine_ls_shift/su_mean         0.0000569


# Computed with no filters except I/sigma = -10 
_oxford_reflns_number_all        6514
_oxford_refine_ls_R_factor_all   0.0298
_oxford_refine_ls_wR_factor_all  0.0833

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                6156
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_gt          0.0820


_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) + ( 0.05P)² + 1.03P] 
 ,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
C1 C 0.68037(15) 0.65348(6) 0.37984(5) 0.0245 1.0000 Uani . . . . . .
C2 C 0.76580(17) 0.71341(6) 0.36285(6) 0.0288 1.0000 Uani . . . . . .
C3 C 0.82633(17) 0.72161(6) 0.30332(6) 0.0306 1.0000 Uani . . . . . .
C4 C 0.80503(17) 0.67031(7) 0.26086(5) 0.0305 1.0000 Uani . . . . . .
C5 C 0.72154(16) 0.60956(6) 0.27727(5) 0.0256 1.0000 Uani . . . . . .
C6 C 0.65942(14) 0.60219(5) 0.33670(5) 0.0206 1.0000 Uani . . . . . .
S7 S 0.54387(3) 0.527661(13) 0.358961(11) 0.0207 1.0000 Uani . . . . . .
O8 O 0.62489(12) 0.50358(4) 0.41514(4) 0.0306 1.0000 Uani . . . . . .
O9 O 0.53347(12) 0.48308(4) 0.30708(4) 0.0296 1.0000 Uani . . . . . .
C10 C 0.32479(15) 0.55714(5) 0.37491(5) 0.0240 1.0000 Uani . . . . . .
C11 C 0.15414(16) 0.55573(6) 0.33593(6) 0.0322 1.0000 Uani . . . . . .
C12 C 0.15973(16) 0.51473(6) 0.39355(6) 0.0263 1.0000 Uani . . . . . .
C13 C 0.23715(18) 0.56720(6) 0.43624(6) 0.0324 1.0000 Uani . . . . . .
C14 C 0.14148(15) 0.44145(6) 0.40332(5) 0.0229 1.0000 Uani . . . . . .
C15 C 0.13209(17) 0.39596(6) 0.35450(5) 0.0286 1.0000 Uani . . . . . .
C16 C 0.11869(17) 0.32696(6) 0.36485(5) 0.0284 1.0000 Uani . . . . . .
C17 C 0.11088(15) 0.30218(6) 0.42443(5) 0.0226 1.0000 Uani . . . . . .
C18 C 0.11486(15) 0.34747(6) 0.47296(5) 0.0246 1.0000 Uani . . . . . .
C19 C 0.13137(15) 0.41641(6) 0.46279(5) 0.0249 1.0000 Uani . . . . . .
C20 C 0.10024(16) 0.22867(6) 0.43933(5) 0.0255 1.0000 Uani . . . . . .
O21 O 0.08479(16) 0.20677(5) 0.49040(4) 0.0421 1.0000 Uani . . . . . .
O22 O 0.11066(14) 0.18931(4) 0.39001(4) 0.0334 1.0000 Uani . . . . . .
C23 C 0.1095(2) 0.11680(6) 0.40115(6) 0.0346 1.0000 Uani . . . . . .
C51 C -0.18179(15) 0.31340(6) 0.12629(5) 0.0237 1.0000 Uani . . . . . .
C52 C -0.27151(16) 0.25430(6) 0.14276(5) 0.0278 1.0000 Uani . . . . . .
C53 C -0.32396(17) 0.24404(6) 0.20295(6) 0.0304 1.0000 Uani . . . . . .
C54 C -0.28982(17) 0.29308(6) 0.24689(5) 0.0301 1.0000 Uani . . . . . .
C55 C -0.20214(15) 0.35315(6) 0.23106(5) 0.0250 1.0000 Uani . . . . . .
C56 C -0.14822(14) 0.36236(5) 0.17101(5) 0.0207 1.0000 Uani . . . . . .
S57 S -0.02823(4) 0.436583(13) 0.150018(12) 0.0213 1.0000 Uani . . . . . .
O58 O -0.10288(13) 0.46039(4) 0.09301(4) 0.0329 1.0000 Uani . . . . . .
O59 O -0.02293(12) 0.48133(4) 0.20192(4) 0.0301 1.0000 Uani . . . . . .
C60 C 0.19361(15) 0.40754(6) 0.13737(5) 0.0244 1.0000 Uani . . . . . .
C61 C 0.36266(16) 0.41611(6) 0.17655(6) 0.0319 1.0000 Uani . . . . . .
C62 C 0.35312(16) 0.45190(6) 0.11627(6) 0.0264 1.0000 Uani . . . . . .
C63 C 0.28573(19) 0.39447(6) 0.07733(6) 0.0343 1.0000 Uani . . . . . .
C64 C 0.36059(15) 0.52437(6) 0.10169(5) 0.0225 1.0000 Uani . . . . . .
C65 C 0.39162(17) 0.57282(6) 0.14711(5) 0.0271 1.0000 Uani . . . . . .
C66 C 0.40081(17) 0.64100(6) 0.13255(5) 0.0274 1.0000 Uani . . . . . .
C67 C 0.38253(15) 0.66214(6) 0.07202(5) 0.0237 1.0000 Uani . . . . . .
C68 C 0.35322(16) 0.61388(6) 0.02662(5) 0.0254 1.0000 Uani . . . . . .
C69 C 0.34155(15) 0.54586(6) 0.04118(5) 0.0249 1.0000 Uani . . . . . .
C70 C 0.39133(16) 0.73471(6) 0.05369(5) 0.0274 1.0000 Uani . . . . . .
O71 O 0.39830(19) 0.75436(5) 0.00183(4) 0.0525 1.0000 Uani . . . . . .
O72 O 0.39025(13) 0.77605(4) 0.10177(4) 0.0328 1.0000 Uani . . . . . .
C73 C 0.39169(19) 0.84800(6) 0.08868(6) 0.0336 1.0000 Uani . . . . . .
H11 H 0.6322 0.6475 0.4195 0.0297 1.0000 Uiso R . . . . .
H21 H 0.7823 0.7485 0.3916 0.0353 1.0000 Uiso R . . . . .
H31 H 0.8852 0.7626 0.2914 0.0378 1.0000 Uiso R . . . . .
H41 H 0.8488 0.6767 0.2213 0.0366 1.0000 Uiso R . . . . .
H51 H 0.7104 0.5727 0.2495 0.0320 1.0000 Uiso R . . . . .
H111 H 0.0791 0.5965 0.3345 0.0409 1.0000 Uiso R . . . . .
H112 H 0.1574 0.5310 0.2977 0.0371 1.0000 Uiso R . . . . .
H131 H 0.1703 0.6090 0.4424 0.0397 1.0000 Uiso R . . . . .
H132 H 0.3036 0.5506 0.4724 0.0387 1.0000 Uiso R . . . . .
H151 H 0.1363 0.4123 0.3140 0.0346 1.0000 Uiso R . . . . .
H161 H 0.1171 0.2963 0.3318 0.0357 1.0000 Uiso R . . . . .
H181 H 0.1063 0.3310 0.5127 0.0297 1.0000 Uiso R . . . . .
H191 H 0.1384 0.4470 0.4967 0.0310 1.0000 Uiso R . . . . .
H232 H 0.0952 0.0964 0.3619 0.0527 1.0000 Uiso R . . . . .
H233 H 0.0110 0.1042 0.4271 0.0523 1.0000 Uiso R . . . . .
H231 H 0.2267 0.1032 0.4188 0.0517 1.0000 Uiso R . . . . .
H511 H -0.1413 0.3203 0.0852 0.0284 1.0000 Uiso R . . . . .
H521 H -0.2975 0.2208 0.1130 0.0345 1.0000 Uiso R . . . . .
H531 H -0.3856 0.2033 0.2139 0.0368 1.0000 Uiso R . . . . .
H541 H -0.3274 0.2866 0.2874 0.0372 1.0000 Uiso R . . . . .
H551 H -0.1845 0.3881 0.2595 0.0306 1.0000 Uiso R . . . . .
H611 H 0.3515 0.4437 0.2129 0.0361 1.0000 Uiso R . . . . .
H612 H 0.4442 0.3780 0.1810 0.0389 1.0000 Uiso R . . . . .
H631 H 0.2137 0.4063 0.0398 0.0415 1.0000 Uiso R . . . . .
H632 H 0.3624 0.3543 0.0739 0.0417 1.0000 Uiso R . . . . .
H651 H 0.4055 0.5595 0.1889 0.0330 1.0000 Uiso R . . . . .
H661 H 0.4201 0.6732 0.1630 0.0352 1.0000 Uiso R . . . . .
H681 H 0.3405 0.6272 -0.0145 0.0310 1.0000 Uiso R . . . . .
H691 H 0.3180 0.5139 0.0106 0.0306 1.0000 Uiso R . . . . .
H732 H 0.4027 0.8703 0.1281 0.0504 1.0000 Uiso R . . . . .
H733 H 0.4935 0.8595 0.0629 0.0490 1.0000 Uiso R . . . . .
H731 H 0.2769 0.8601 0.0696 0.0505 1.0000 Uiso R . . . . .

_refine_ls_extinction_coef       21(3)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          2.407(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
C1 . C2 . 1.3871(16) yes
C1 . C6 . 1.3921(15) yes
C1 . H11 . 0.946 no
C2 . C3 . 1.3871(17) yes
C2 . H21 . 0.942 no
C3 . C4 . 1.3824(17) yes
C3 . H31 . 0.951 no
C4 . C5 . 1.3916(16) yes
C4 . H41 . 0.932 no
C5 . C6 . 1.3867(15) yes
C5 . H51 . 0.950 no
C6 . S7 . 1.7629(11) yes
S7 . O8 . 1.4385(8) yes
S7 . O9 . 1.4382(8) yes
S7 . C10 . 1.7254(11) yes
C10 . C11 . 1.4945(16) yes
C10 . C12 . 1.5163(15) yes
C10 . C13 . 1.5018(16) yes
C11 . C12 . 1.4988(17) yes
C11 . H111 . 0.971 no
C11 . H112 . 0.969 no
C12 . C13 . 1.5007(17) yes
C12 . C14 . 1.4691(16) yes
C13 . H131 . 0.968 no
C13 . H132 . 0.980 no
C14 . C15 . 1.3971(16) yes
C14 . C19 . 1.3946(16) yes
C15 . C16 . 1.3849(17) yes
C15 . H151 . 0.944 no
C16 . C17 . 1.3942(15) yes
C16 . H161 . 0.945 no
C17 . C18 . 1.3888(15) yes
C17 . C20 . 1.4901(15) yes
C18 . C19 . 1.3850(16) yes
C18 . H181 . 0.930 no
C19 . H191 . 0.957 no
C20 . O21 . 1.2044(14) yes
C20 . O22 . 1.3327(14) yes
O22 . C23 . 1.4526(14) yes
C23 . H232 . 0.953 no
C23 . H233 . 0.948 no
C23 . H231 . 0.966 no
C51 . C52 . 1.3844(16) yes
C51 . C56 . 1.3958(15) yes
C51 . H511 . 0.957 no
C52 . C53 . 1.3882(17) yes
C52 . H521 . 0.946 no
C53 . C54 . 1.3856(17) yes
C53 . H531 . 0.951 no
C54 . C55 . 1.3901(17) yes
C54 . H541 . 0.939 no
C55 . C56 . 1.3855(15) yes
C55 . H551 . 0.938 no
C56 . S57 . 1.7659(11) yes
S57 . O58 . 1.4348(9) yes
S57 . O59 . 1.4394(8) yes
S57 . C60 . 1.7273(11) yes
C60 . C61 . 1.4970(16) yes
C60 . C62 . 1.5225(15) yes
C60 . C63 . 1.4998(16) yes
C61 . C62 . 1.4977(17) yes
C61 . H611 . 0.968 no
C61 . H612 . 0.960 no
C62 . C63 . 1.4977(16) yes
C62 . C64 . 1.4676(16) yes
C63 . H631 . 0.996 no
C63 . H632 . 0.970 no
C64 . C65 . 1.3966(15) yes
C64 . C69 . 1.3963(16) yes
C65 . C66 . 1.3854(16) yes
C65 . H651 . 0.957 no
C66 . C67 . 1.3942(16) yes
C66 . H661 . 0.931 no
C67 . C68 . 1.3918(15) yes
C67 . C70 . 1.4897(16) yes
C68 . C69 . 1.3834(16) yes
C68 . H681 . 0.942 no
C69 . H691 . 0.935 no
C70 . O71 . 1.2009(15) yes
C70 . O72 . 1.3320(14) yes
O72 . C73 . 1.4497(14) yes
C73 . H732 . 0.971 no
C73 . H733 . 0.958 no
C73 . H731 . 0.956 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 . C1 . C6 . 119.05(10) yes
C2 . C1 . H11 . 121.3 no
C6 . C1 . H11 . 119.6 no
C1 . C2 . C3 . 119.71(11) yes
C1 . C2 . H21 . 120.2 no
C3 . C2 . H21 . 120.1 no
C2 . C3 . C4 . 120.75(11) yes
C2 . C3 . H31 . 120.1 no
C4 . C3 . H31 . 119.1 no
C3 . C4 . C5 . 120.32(11) yes
C3 . C4 . H41 . 119.2 no
C5 . C4 . H41 . 120.4 no
C4 . C5 . C6 . 118.47(10) yes
C4 . C5 . H51 . 122.0 no
C6 . C5 . H51 . 119.5 no
C1 . C6 . C5 . 121.69(10) yes
C1 . C6 . S7 . 118.00(8) yes
C5 . C6 . S7 . 120.28(8) yes
C6 . S7 . O8 . 108.76(5) yes
C6 . S7 . O9 . 108.37(5) yes
O8 . S7 . O9 . 119.38(5) yes
C6 . S7 . C10 . 102.22(5) yes
O8 . S7 . C10 . 107.88(5) yes
O9 . S7 . C10 . 108.89(5) yes
S7 . C10 . C11 . 129.28(9) yes
S7 . C10 . C12 . 126.39(8) yes
C11 . C10 . C12 . 59.70(8) yes
S7 . C10 . C13 . 128.27(9) yes
C11 . C10 . C13 . 99.24(10) yes
C12 . C10 . C13 . 59.63(8) yes
C10 . C11 . C12 . 60.87(8) yes
C10 . C11 . H111 . 117.5 no
C12 . C11 . H111 . 119.1 no
C10 . C11 . H112 . 118.5 no
C12 . C11 . H112 . 117.0 no
H111 . C11 . H112 . 114.0 no
C10 . C12 . C11 . 59.43(8) yes
C10 . C12 . C13 . 59.71(7) yes
C11 . C12 . C13 . 99.11(10) yes
C10 . C12 . C14 . 130.93(10) yes
C11 . C12 . C14 . 130.76(11) yes
C13 . C12 . C14 . 128.54(11) yes
C10 . C13 . C12 . 60.66(7) yes
C10 . C13 . H131 . 116.9 no
C12 . C13 . H131 . 119.5 no
C10 . C13 . H132 . 118.1 no
C12 . C13 . H132 . 116.8 no
H131 . C13 . H132 . 114.5 no
C12 . C14 . C15 . 121.74(10) yes
C12 . C14 . C19 . 119.37(10) yes
C15 . C14 . C19 . 118.88(10) yes
C14 . C15 . C16 . 120.71(11) yes
C14 . C15 . H151 . 119.7 no
C16 . C15 . H151 . 119.6 no
C15 . C16 . C17 . 120.12(11) yes
C15 . C16 . H161 . 120.4 no
C17 . C16 . H161 . 119.4 no
C16 . C17 . C18 . 119.23(10) yes
C16 . C17 . C20 . 123.32(10) yes
C18 . C17 . C20 . 117.45(10) yes
C17 . C18 . C19 . 120.77(10) yes
C17 . C18 . H181 . 119.2 no
C19 . C18 . H181 . 120.0 no
C14 . C19 . C18 . 120.25(10) yes
C14 . C19 . H191 . 119.7 no
C18 . C19 . H191 . 120.0 no
C17 . C20 . O21 . 123.93(11) yes
C17 . C20 . O22 . 112.81(9) yes
O21 . C20 . O22 . 123.25(11) yes
C20 . O22 . C23 . 116.01(9) yes
O22 . C23 . H232 . 105.4 no
O22 . C23 . H233 . 111.4 no
H232 . C23 . H233 . 110.6 no
O22 . C23 . H231 . 109.6 no
H232 . C23 . H231 . 109.4 no
H233 . C23 . H231 . 110.3 no
C52 . C51 . C56 . 118.74(10) yes
C52 . C51 . H511 . 120.8 no
C56 . C51 . H511 . 120.5 no
C51 . C52 . C53 . 120.13(11) yes
C51 . C52 . H521 . 120.1 no
C53 . C52 . H521 . 119.8 no
C52 . C53 . C54 . 120.53(11) yes
C52 . C53 . H531 . 119.6 no
C54 . C53 . H531 . 119.9 no
C53 . C54 . C55 . 120.18(11) yes
C53 . C54 . H541 . 120.6 no
C55 . C54 . H541 . 119.2 no
C54 . C55 . C56 . 118.72(10) yes
C54 . C55 . H551 . 121.6 no
C56 . C55 . H551 . 119.6 no
C51 . C56 . C55 . 121.69(10) yes
C51 . C56 . S57 . 118.41(8) yes
C55 . C56 . S57 . 119.88(8) yes
C56 . S57 . O58 . 108.43(5) yes
C56 . S57 . O59 . 108.33(5) yes
O58 . S57 . O59 . 119.51(5) yes
C56 . S57 . C60 . 102.97(5) yes
O58 . S57 . C60 . 108.23(6) yes
O59 . S57 . C60 . 108.13(5) yes
S57 . C60 . C61 . 128.71(9) yes
S57 . C60 . C62 . 124.31(8) yes
C61 . C60 . C62 . 59.46(8) yes
S57 . C60 . C63 . 128.06(10) yes
C61 . C60 . C63 . 98.93(10) yes
C62 . C60 . C63 . 59.41(7) yes
C60 . C61 . C62 . 61.11(8) yes
C60 . C61 . H611 . 117.5 no
C62 . C61 . H611 . 117.0 no
C60 . C61 . H612 . 117.8 no
C62 . C61 . H612 . 118.9 no
H611 . C61 . H612 . 114.4 no
C60 . C62 . C61 . 59.42(8) yes
C60 . C62 . C63 . 59.54(7) yes
C61 . C62 . C63 . 99.00(10) yes
C60 . C62 . C64 . 131.02(10) yes
C61 . C62 . C64 . 130.56(11) yes
C63 . C62 . C64 . 128.84(11) yes
C60 . C63 . C62 . 61.05(7) yes
C60 . C63 . H631 . 116.6 no
C62 . C63 . H631 . 117.2 no
C60 . C63 . H632 . 117.8 no
C62 . C63 . H632 . 118.7 no
H631 . C63 . H632 . 115.0 no
C62 . C64 . C65 . 121.29(10) yes
C62 . C64 . C69 . 119.94(10) yes
C65 . C64 . C69 . 118.74(10) yes
C64 . C65 . C66 . 120.66(11) yes
C64 . C65 . H651 . 120.5 no
C66 . C65 . H651 . 118.9 no
C65 . C66 . C67 . 120.35(11) yes
C65 . C66 . H661 . 120.4 no
C67 . C66 . H661 . 119.2 no
C66 . C67 . C68 . 119.07(10) yes
C66 . C67 . C70 . 122.69(10) yes
C68 . C67 . C70 . 118.24(10) yes
C67 . C68 . C69 . 120.65(10) yes
C67 . C68 . H681 . 120.3 no
C69 . C68 . H681 . 119.1 no
C64 . C69 . C68 . 120.52(10) yes
C64 . C69 . H691 . 119.4 no
C68 . C69 . H691 . 120.1 no
C67 . C70 . O71 . 124.58(11) yes
C67 . C70 . O72 . 112.12(10) yes
O71 . C70 . O72 . 123.30(11) yes
C70 . O72 . C73 . 116.41(9) yes
O72 . C73 . H732 . 105.7 no
O72 . C73 . H733 . 110.8 no
H732 . C73 . H733 . 111.0 no
O72 . C73 . H731 . 108.9 no
H732 . C73 . H731 . 109.9 no
H733 . C73 . H731 . 110.6 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
C4 . H41 . O22 4_655 167 0.93 2.47 3.3829(17) yes
C54 . H541 . O72 4_545 173 0.94 2.48 3.4125(17) yes
C61 . H611 . O9 . 142 0.97 2.56 3.3734(17) yes


####################################################################### 
# 
# 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_11-150K
_database_code_depnum_ccdc_archive 'CCDC 2074460'
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2021-03-31 deposited with the CCDC.	2021-04-27 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2019-11-26
_audit_creation_method           'CRYSTALS_ver_14.61_build_7356 '

_oxford_structure_analysis_title '7246 Cassie 150K'
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   6.19930(10)
_cell_length_b                   22.8971(3)
_cell_length_c                   27.5542(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3911.21(9)

_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,z+1/2
x+1/2,-y+1/2,-z
-x,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'
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            12

# Given Formula = C16 H14 O2 S1 
# Dc =      1.38 Fooo =   1704.00 Mu =     21.56 M =    270.35
# Found Formula = C16 H14 O2 S1 
# Dc =      1.38 FOOO =   1704.00 Mu =     21.56 M =    270.35

_chemical_formula_sum            'C16 H14 O2 S'
_chemical_formula_moiety         'C16 H14 O2 S'
_chemical_compound_source        .
_chemical_formula_weight         270.35


_cell_measurement_reflns_used    10878
_cell_measurement_theta_min      3.82
_cell_measurement_theta_max      76.13
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.04
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_max          0.22

_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1704
_exptl_absorpt_coefficient_mu    2.156

# Sheldrick geometric approximatio 0.68 0.92 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.92
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_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 (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_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            22609
_diffrn_reflns_av_unetI/netI     0.049
_reflns_number_total             8095
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_av_sigmaI/netI    0.0491
# Number of reflections without Friedels Law is 8095 
# Number of reflections with Friedels Law is 4625 
# Theoretical number of reflections is about 4099 

_diffrn_reflns_theta_min         3.744
_diffrn_reflns_theta_max         76.292
_diffrn_measured_fraction_theta_max 0.992

_diffrn_reflns_theta_full        74.767
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_reflns_limit_h_min              -7
_reflns_limit_h_max              7
_reflns_limit_k_min              0
_reflns_limit_k_max              28
_reflns_limit_l_min              0
_reflns_limit_l_max              34

_oxford_diffrn_Wilson_B_factor   1.78
_oxford_diffrn_Wilson_scale      0.24

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

_refine_diff_density_min         -0.26
_refine_diff_density_max         0.32


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

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
_oxford_refine_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     515
_refine_ls_number_reflns         8095
_oxford_refine_ls_R_factor_ref   0.0342
_refine_ls_wR_factor_ref         0.0824
_refine_ls_goodness_of_fit_ref   1.0069
_refine_ls_shift/su_max          0.0010746
_refine_ls_shift/su_mean         0.0000786


# Computed with no filters except I/sigma = -10 
_oxford_reflns_number_all        8095
_refine_ls_R_factor_all          0.0342
_refine_ls_wR_factor_all         0.0824

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                7636
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_gt          0.0783

# For an explanation, see Cooper & Watkin, Acta Cryst. (2016). B72, 661-683 
_oxford_Hooft_y                  0.033(6) # for 3403 Friedel pairs 
_oxford_Bijvoet_difference       0.028(6) # for 3403 Friedel pairs 
# (Similar to the Parsons(q).) 
_oxford_refined_Flack_x          0.017(9) # for 3470 Friedel pairs 
_refine_ls_abs_structure_Flack   0.028(6)
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 3403 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) + ( 0.05P)² + 0.05P] 
 ,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
C1 C 0.4492(3) 0.67303(8) 0.74448(6) 0.0327 1.0000 Uani . . . . . .
C2 C 0.3945(5) 0.67552(8) 0.79338(7) 0.0446 1.0000 Uani . . . . . .
C3 C 0.1978(5) 0.65499(9) 0.80914(7) 0.0452 1.0000 Uani . . . . . .
C4 C 0.0526(4) 0.63107(9) 0.77659(8) 0.0421 1.0000 Uani . . . . . .
C5 C 0.1035(3) 0.62810(8) 0.72748(7) 0.0317 1.0000 Uani . . . . . .
C6 C 0.3021(3) 0.64888(7) 0.71224(5) 0.0231 1.0000 Uani . . . . . .
S7 S 0.36854(6) 0.644725(16) 0.649869(14) 0.0212 1.0000 Uani . . . . . .
O8 O 0.5996(2) 0.64900(6) 0.64501(5) 0.0319 1.0000 Uani . . . . . .
O9 O 0.2604(2) 0.59444(5) 0.63034(4) 0.0283 1.0000 Uani . . . . . .
C10 C 0.2547(3) 0.70666(7) 0.62510(6) 0.0228 1.0000 Uani . . . . . .
C11 C 0.3672(3) 0.75967(7) 0.60524(6) 0.0262 1.0000 Uani . . . . . .
C12 C 0.2410(3) 0.72116(7) 0.57157(6) 0.0219 1.0000 Uani . . . . . .
C13 C 0.0397(3) 0.71455(7) 0.60071(6) 0.0252 1.0000 Uani . . . . . .
C14 C 0.3022(2) 0.68896(6) 0.52736(5) 0.0206 1.0000 Uani . . . . . .
C15 C 0.5142(3) 0.67122(7) 0.51811(6) 0.0247 1.0000 Uani . . . . . .
C16 C 0.5622(3) 0.63993(7) 0.47647(6) 0.0269 1.0000 Uani . . . . . .
C17 C 0.4007(3) 0.62605(6) 0.44335(6) 0.0242 1.0000 Uani . . . . . .
C18 C 0.1900(3) 0.64405(7) 0.45217(6) 0.0250 1.0000 Uani . . . . . .
C19 C 0.1420(3) 0.67556(7) 0.49369(6) 0.0235 1.0000 Uani . . . . . .
C25 C 0.6427(3) 0.53941(8) 0.27530(7) 0.0357 1.0000 Uani . . . . . .
C24 C 0.6024(5) 0.53304(10) 0.22593(8) 0.0526 1.0000 Uani . . . . . .
C23 C 0.7573(6) 0.50900(9) 0.19577(7) 0.0562 1.0000 Uani . . . . . .
C22 C 0.9544(5) 0.49227(9) 0.21365(7) 0.0516 1.0000 Uani . . . . . .
C21 C 0.9993(4) 0.49791(8) 0.26290(7) 0.0371 1.0000 Uani . . . . . .
C26 C 0.8421(3) 0.52139(7) 0.29282(6) 0.0241 1.0000 Uani . . . . . .
S27 S 0.89511(6) 0.528347(15) 0.355571(13) 0.0215 1.0000 Uani . . . . . .
O28 O 1.1251(2) 0.52537(6) 0.36288(5) 0.0336 1.0000 Uani . . . . . .
O29 O 0.7793(2) 0.57873(5) 0.37285(4) 0.0290 1.0000 Uani . . . . . .
C30 C 0.7797(3) 0.46657(7) 0.38003(6) 0.0236 1.0000 Uani . . . . . .
C33 C 0.5568(3) 0.45795(7) 0.40032(6) 0.0259 1.0000 Uani . . . . . .
C32 C 0.7479(3) 0.45192(7) 0.43304(6) 0.0228 1.0000 Uani . . . . . .
C31 C 0.8869(3) 0.41360(7) 0.40156(6) 0.0289 1.0000 Uani . . . . . .
C34 C 0.7955(3) 0.48417(6) 0.47812(6) 0.0209 1.0000 Uani . . . . . .
C39 C 0.6287(3) 0.49574(7) 0.51045(6) 0.0236 1.0000 Uani . . . . . .
C38 C 0.6665(3) 0.52639(7) 0.55322(6) 0.0254 1.0000 Uani . . . . . .
C37 C 0.8734(3) 0.54580(7) 0.56386(6) 0.0249 1.0000 Uani . . . . . .
C36 C 1.0419(3) 0.53431(7) 0.53174(6) 0.0270 1.0000 Uani . . . . . .
C35 C 1.0038(3) 0.50349(7) 0.48916(6) 0.0258 1.0000 Uani . . . . . .
C45 C 0.0604(3) 0.29513(8) 0.72996(7) 0.0336 1.0000 Uani . . . . . .
C44 C 0.0342(4) 0.30061(10) 0.77985(7) 0.0460 1.0000 Uani . . . . . .
C43 C 0.2004(5) 0.32339(9) 0.80796(7) 0.0477 1.0000 Uani . . . . . .
C42 C 0.3935(5) 0.34021(8) 0.78681(7) 0.0432 1.0000 Uani . . . . . .
C41 C 0.4212(3) 0.33513(7) 0.73699(7) 0.0324 1.0000 Uani . . . . . .
C46 C 0.2535(3) 0.31254(6) 0.70924(5) 0.0235 1.0000 Uani . . . . . .
S47 S 0.28528(6) 0.307121(16) 0.645700(13) 0.0224 1.0000 Uani . . . . . .
O49 O 0.1579(2) 0.25847(5) 0.62934(4) 0.0325 1.0000 Uani . . . . . .
O48 O 0.5125(2) 0.30830(6) 0.63509(5) 0.0340 1.0000 Uani . . . . . .
C50 C 0.1723(3) 0.37094(7) 0.62398(6) 0.0247 1.0000 Uani . . . . . .
C53 C -0.0492(3) 0.38114(8) 0.60382(6) 0.0300 1.0000 Uani . . . . . .
C52 C 0.1408(3) 0.38620(7) 0.57074(6) 0.0248 1.0000 Uani . . . . . .
C51 C 0.2851(3) 0.42259(7) 0.60205(6) 0.0292 1.0000 Uani . . . . . .
C54 C 0.1833(3) 0.35384(7) 0.52559(6) 0.0223 1.0000 Uani . . . . . .
C59 C 0.0158(3) 0.32345(7) 0.50322(6) 0.0264 1.0000 Uani . . . . . .
C58 C 0.0517(3) 0.29231(7) 0.46068(6) 0.0280 1.0000 Uani . . . . . .
C57 C 0.2556(3) 0.29173(7) 0.43956(6) 0.0292 1.0000 Uani . . . . . .
C56 C 0.4226(3) 0.32280(7) 0.46134(6) 0.0299 1.0000 Uani . . . . . .
C55 C 0.3878(3) 0.35355(7) 0.50400(6) 0.0269 1.0000 Uani . . . . . .
H11 H 0.5844 0.6861 0.7332 0.0390 1.0000 Uiso R . . . . .
H21 H 0.4885 0.6912 0.8163 0.0553 1.0000 Uiso R . . . . .
H31 H 0.1655 0.6563 0.8423 0.0534 1.0000 Uiso R . . . . .
H41 H -0.0801 0.6159 0.7878 0.0500 1.0000 Uiso R . . . . .
H51 H 0.0085 0.6132 0.7049 0.0387 1.0000 Uiso R . . . . .
H111 H 0.3104 0.7983 0.6135 0.0316 1.0000 Uiso R . . . . .
H112 H 0.5193 0.7595 0.6021 0.0325 1.0000 Uiso R . . . . .
H131 H -0.0496 0.7485 0.6085 0.0307 1.0000 Uiso R . . . . .
H132 H -0.0454 0.6797 0.5956 0.0295 1.0000 Uiso R . . . . .
H151 H 0.6218 0.6795 0.5399 0.0301 1.0000 Uiso R . . . . .
H161 H 0.7053 0.6278 0.4702 0.0317 1.0000 Uiso R . . . . .
H171 H 0.4332 0.6046 0.4154 0.0295 1.0000 Uiso R . . . . .
H181 H 0.0843 0.6351 0.4301 0.0304 1.0000 Uiso R . . . . .
H191 H 0.0014 0.6894 0.4990 0.0269 1.0000 Uiso R . . . . .
H251 H 0.5424 0.5543 0.2964 0.0431 1.0000 Uiso R . . . . .
H241 H 0.4705 0.5453 0.2128 0.0639 1.0000 Uiso R . . . . .
H231 H 0.7301 0.5047 0.1623 0.0665 1.0000 Uiso R . . . . .
H221 H 1.0608 0.4761 0.1927 0.0616 1.0000 Uiso R . . . . .
H211 H 1.1317 0.4862 0.2756 0.0451 1.0000 Uiso R . . . . .
H331 H 0.4658 0.4923 0.4032 0.0306 1.0000 Uiso R . . . . .
H332 H 0.4782 0.4231 0.3909 0.0313 1.0000 Uiso R . . . . .
H311 H 1.0410 0.4139 0.4068 0.0343 1.0000 Uiso R . . . . .
H312 H 0.8334 0.3753 0.3929 0.0355 1.0000 Uiso R . . . . .
H391 H 0.4944 0.4819 0.5029 0.0286 1.0000 Uiso R . . . . .
H381 H 0.5543 0.5341 0.5746 0.0303 1.0000 Uiso R . . . . .
H371 H 0.9000 0.5665 0.5927 0.0298 1.0000 Uiso R . . . . .
H361 H 1.1830 0.5471 0.5386 0.0323 1.0000 Uiso R . . . . .
H351 H 1.1164 0.4971 0.4677 0.0319 1.0000 Uiso R . . . . .
H451 H -0.0520 0.2812 0.7107 0.0415 1.0000 Uiso R . . . . .
H441 H -0.0960 0.2885 0.7947 0.0555 1.0000 Uiso R . . . . .
H431 H 0.1858 0.3267 0.8415 0.0571 1.0000 Uiso R . . . . .
H421 H 0.5070 0.3550 0.8060 0.0528 1.0000 Uiso R . . . . .
H411 H 0.5532 0.3463 0.7213 0.0389 1.0000 Uiso R . . . . .
H531 H -0.1258 0.4150 0.6135 0.0362 1.0000 Uiso R . . . . .
H532 H -0.1436 0.3478 0.6000 0.0355 1.0000 Uiso R . . . . .
H511 H 0.2391 0.4610 0.6115 0.0349 1.0000 Uiso R . . . . .
H512 H 0.4405 0.4202 0.5968 0.0348 1.0000 Uiso R . . . . .
H591 H -0.1242 0.3235 0.5168 0.0322 1.0000 Uiso R . . . . .
H581 H -0.0600 0.2720 0.4464 0.0350 1.0000 Uiso R . . . . .
H571 H 0.2799 0.2709 0.4115 0.0344 1.0000 Uiso R . . . . .
H561 H 0.5603 0.3219 0.4471 0.0367 1.0000 Uiso R . . . . .
H551 H 0.4986 0.3742 0.5178 0.0322 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          2.106(11)
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
C1 . C2 . 1.391(3) yes
C1 . C6 . 1.388(2) yes
C1 . H11 . 0.942 no
C2 . C3 . 1.377(4) yes
C2 . H21 . 0.932 no
C3 . C4 . 1.384(3) yes
C3 . H31 . 0.937 no
C4 . C5 . 1.391(3) yes
C4 . H41 . 0.944 no
C5 . C6 . 1.385(3) yes
C5 . H51 . 0.922 no
C6 . S7 . 1.7698(16) yes
S7 . O8 . 1.4422(13) yes
S7 . O9 . 1.4369(12) yes
S7 . C10 . 1.7247(16) yes
C10 . C11 . 1.503(2) yes
C10 . C12 . 1.514(2) yes
C10 . C13 . 1.504(2) yes
C11 . C12 . 1.500(2) yes
C11 . H111 . 0.979 no
C11 . H112 . 0.947 no
C12 . C13 . 1.491(2) yes
C12 . C14 . 1.473(2) yes
C13 . H131 . 0.978 no
C13 . H132 . 0.967 no
C14 . C15 . 1.399(2) yes
C14 . C19 . 1.393(2) yes
C15 . C16 . 1.385(2) yes
C15 . H151 . 0.917 no
C16 . C17 . 1.392(2) yes
C16 . H161 . 0.946 no
C17 . C18 . 1.391(2) yes
C17 . H171 . 0.937 no
C18 . C19 . 1.385(2) yes
C18 . H181 . 0.917 no
C19 . H191 . 0.939 no
C25 . C24 . 1.391(3) yes
C25 . C26 . 1.390(3) yes
C25 . H251 . 0.916 no
C24 . C23 . 1.384(4) yes
C24 . H241 . 0.937 no
C23 . C22 . 1.372(4) yes
C23 . H231 . 0.942 no
C22 . C21 . 1.391(3) yes
C22 . H221 . 0.951 no
C21 . C26 . 1.385(3) yes
C21 . H211 . 0.932 no
C26 . S27 . 1.7672(16) yes
S27 . O28 . 1.4414(13) yes
S27 . O29 . 1.4398(12) yes
S27 . C30 . 1.7224(17) yes
C30 . C33 . 1.504(2) yes
C30 . C32 . 1.512(2) yes
C30 . C31 . 1.505(2) yes
C33 . C32 . 1.495(2) yes
C33 . H331 . 0.972 no
C33 . H332 . 0.970 no
C32 . C31 . 1.505(2) yes
C32 . C34 . 1.475(2) yes
C31 . H311 . 0.966 no
C31 . H312 . 0.967 no
C34 . C39 . 1.390(2) yes
C34 . C35 . 1.398(2) yes
C39 . C38 . 1.391(2) yes
C39 . H391 . 0.915 no
C38 . C37 . 1.389(2) yes
C38 . H381 . 0.929 no
C37 . C36 . 1.394(2) yes
C37 . H371 . 0.940 no
C36 . C35 . 1.390(2) yes
C36 . H361 . 0.941 no
C35 . H351 . 0.927 no
C45 . C44 . 1.390(3) yes
C45 . C46 . 1.385(2) yes
C45 . H451 . 0.932 no
C44 . C43 . 1.391(4) yes
C44 . H441 . 0.946 no
C43 . C42 . 1.386(4) yes
C43 . H431 . 0.931 no
C42 . C41 . 1.388(3) yes
C42 . H421 . 0.944 no
C41 . C46 . 1.391(2) yes
C41 . H411 . 0.960 no
C46 . S47 . 1.7663(16) yes
S47 . O49 . 1.4379(13) yes
S47 . O48 . 1.4389(13) yes
S47 . C50 . 1.7273(17) yes
C50 . C53 . 1.500(2) yes
C50 . C52 . 1.521(2) yes
C50 . C51 . 1.501(2) yes
C53 . C52 . 1.494(2) yes
C53 . H531 . 0.948 no
C53 . H532 . 0.967 no
C52 . C51 . 1.496(2) yes
C52 . C54 . 1.472(2) yes
C51 . H511 . 0.961 no
C51 . H512 . 0.975 no
C54 . C59 . 1.394(2) yes
C54 . C55 . 1.400(2) yes
C59 . C58 . 1.390(2) yes
C59 . H591 . 0.945 no
C58 . C57 . 1.392(3) yes
C58 . H581 . 0.923 no
C57 . C56 . 1.392(3) yes
C57 . H571 . 0.921 no
C56 . C55 . 1.387(2) yes
C56 . H561 . 0.939 no
C55 . H551 . 0.917 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 . C1 . C6 . 118.43(19) yes
C2 . C1 . H11 . 121.5 no
C6 . C1 . H11 . 120.0 no
C1 . C2 . C3 . 120.50(19) yes
C1 . C2 . H21 . 121.4 no
C3 . C2 . H21 . 118.1 no
C2 . C3 . C4 . 120.46(18) yes
C2 . C3 . H31 . 119.1 no
C4 . C3 . H31 . 120.4 no
C3 . C4 . C5 . 120.1(2) yes
C3 . C4 . H41 . 120.1 no
C5 . C4 . H41 . 119.8 no
C4 . C5 . C6 . 118.69(19) yes
C4 . C5 . H51 . 121.9 no
C6 . C5 . H51 . 119.4 no
C1 . C6 . C5 . 121.79(16) yes
C1 . C6 . S7 . 119.33(14) yes
C5 . C6 . S7 . 118.88(13) yes
C6 . S7 . O8 . 108.53(8) yes
C6 . S7 . O9 . 107.33(8) yes
O8 . S7 . O9 . 118.90(8) yes
C6 . S7 . C10 . 104.17(7) yes
O8 . S7 . C10 . 108.29(8) yes
O9 . S7 . C10 . 108.65(7) yes
S7 . C10 . C11 . 128.20(12) yes
S7 . C10 . C12 . 126.07(11) yes
C11 . C10 . C12 . 59.62(10) yes
S7 . C10 . C13 . 129.67(12) yes
C11 . C10 . C13 . 98.70(13) yes
C12 . C10 . C13 . 59.23(10) yes
C10 . C11 . C12 . 60.57(10) yes
C10 . C11 . H111 . 118.6 no
C12 . C11 . H111 . 119.2 no
C10 . C11 . H112 . 119.4 no
C12 . C11 . H112 . 117.4 no
H111 . C11 . H112 . 112.5 no
C10 . C12 . C11 . 59.81(10) yes
C10 . C12 . C13 . 60.02(10) yes
C11 . C12 . C13 . 99.38(13) yes
C10 . C12 . C14 . 132.92(14) yes
C11 . C12 . C14 . 132.16(14) yes
C13 . C12 . C14 . 127.56(14) yes
C10 . C13 . C12 . 60.75(10) yes
C10 . C13 . H131 . 119.9 no
C12 . C13 . H131 . 120.8 no
C10 . C13 . H132 . 116.7 no
C12 . C13 . H132 . 117.5 no
H131 . C13 . H132 . 112.2 no
C12 . C14 . C15 . 122.53(14) yes
C12 . C14 . C19 . 118.51(14) yes
C15 . C14 . C19 . 118.96(14) yes
C14 . C15 . C16 . 120.19(15) yes
C14 . C15 . H151 . 120.3 no
C16 . C15 . H151 . 119.5 no
C15 . C16 . C17 . 120.46(15) yes
C15 . C16 . H161 . 120.3 no
C17 . C16 . H161 . 119.2 no
C16 . C17 . C18 . 119.56(15) yes
C16 . C17 . H171 . 120.3 no
C18 . C17 . H171 . 120.1 no
C17 . C18 . C19 . 120.02(15) yes
C17 . C18 . H181 . 119.3 no
C19 . C18 . H181 . 120.7 no
C14 . C19 . C18 . 120.79(15) yes
C14 . C19 . H191 . 119.0 no
C18 . C19 . H191 . 120.2 no
C24 . C25 . C26 . 117.9(2) yes
C24 . C25 . H251 . 122.4 no
C26 . C25 . H251 . 119.6 no
C25 . C24 . C23 . 120.3(2) yes
C25 . C24 . H241 . 120.2 no
C23 . C24 . H241 . 119.6 no
C24 . C23 . C22 . 120.90(19) yes
C24 . C23 . H231 . 120.2 no
C22 . C23 . H231 . 118.8 no
C23 . C22 . C21 . 120.2(2) yes
C23 . C22 . H221 . 120.6 no
C21 . C22 . H221 . 119.2 no
C22 . C21 . C26 . 118.4(2) yes
C22 . C21 . H211 . 121.1 no
C26 . C21 . H211 . 120.5 no
C25 . C26 . C21 . 122.30(17) yes
C25 . C26 . S27 . 118.59(14) yes
C21 . C26 . S27 . 119.11(14) yes
C26 . S27 . O28 . 108.44(8) yes
C26 . S27 . O29 . 107.64(8) yes
O28 . S27 . O29 . 119.00(8) yes
C26 . S27 . C30 . 103.39(8) yes
O28 . S27 . C30 . 108.49(8) yes
O29 . S27 . C30 . 108.76(8) yes
S27 . C30 . C33 . 129.41(12) yes
S27 . C30 . C32 . 127.92(12) yes
C33 . C30 . C32 . 59.46(10) yes
S27 . C30 . C31 . 129.26(13) yes
C33 . C30 . C31 . 98.83(13) yes
C32 . C30 . C31 . 59.85(10) yes
C30 . C33 . C32 . 60.52(10) yes
C30 . C33 . H331 . 117.2 no
C32 . C33 . H331 . 119.0 no
C30 . C33 . H332 . 118.0 no
C32 . C33 . H332 . 118.8 no
H331 . C33 . H332 . 113.4 no
C30 . C32 . C33 . 60.02(10) yes
C30 . C32 . C31 . 59.85(10) yes
C33 . C32 . C31 . 99.21(13) yes
C30 . C32 . C34 . 132.58(14) yes
C33 . C32 . C34 . 128.32(14) yes
C31 . C32 . C34 . 131.51(15) yes
C32 . C31 . C30 . 60.30(10) yes
C32 . C31 . H311 . 118.3 no
C30 . C31 . H311 . 119.3 no
C32 . C31 . H312 . 118.3 no
C30 . C31 . H312 . 118.8 no
H311 . C31 . H312 . 112.6 no
C32 . C34 . C39 . 119.08(15) yes
C32 . C34 . C35 . 121.76(15) yes
C39 . C34 . C35 . 119.15(15) yes
C34 . C39 . C38 . 120.89(15) yes
C34 . C39 . H391 . 117.7 no
C38 . C39 . H391 . 121.4 no
C39 . C38 . C37 . 119.73(15) yes
C39 . C38 . H381 . 120.5 no
C37 . C38 . H381 . 119.8 no
C38 . C37 . C36 . 119.82(15) yes
C38 . C37 . H371 . 120.1 no
C36 . C37 . H371 . 120.1 no
C37 . C36 . C35 . 120.30(15) yes
C37 . C36 . H361 . 120.7 no
C35 . C36 . H361 . 119.0 no
C34 . C35 . C36 . 120.10(15) yes
C34 . C35 . H351 . 120.4 no
C36 . C35 . H351 . 119.4 no
C44 . C45 . C46 . 118.85(19) yes
C44 . C45 . H451 . 120.4 no
C46 . C45 . H451 . 120.7 no
C45 . C44 . C43 . 119.9(2) yes
C45 . C44 . H441 . 120.0 no
C43 . C44 . H441 . 120.1 no
C44 . C43 . C42 . 120.66(18) yes
C44 . C43 . H431 . 120.7 no
C42 . C43 . H431 . 118.6 no
C43 . C42 . C41 . 120.0(2) yes
C43 . C42 . H421 . 120.5 no
C41 . C42 . H421 . 119.5 no
C42 . C41 . C46 . 118.82(19) yes
C42 . C41 . H411 . 121.9 no
C46 . C41 . H411 . 119.3 no
C41 . C46 . C45 . 121.80(16) yes
C41 . C46 . S47 . 119.19(13) yes
C45 . C46 . S47 . 118.99(13) yes
C46 . S47 . O49 . 107.70(7) yes
C46 . S47 . O48 . 108.01(8) yes
O49 . S47 . O48 . 119.24(8) yes
C46 . S47 . C50 . 103.81(8) yes
O49 . S47 . C50 . 108.92(8) yes
O48 . S47 . C50 . 108.10(8) yes
S47 . C50 . C53 . 129.14(13) yes
S47 . C50 . C52 . 125.49(12) yes
C53 . C50 . C52 . 59.29(11) yes
S47 . C50 . C51 . 128.10(13) yes
C53 . C50 . C51 . 98.91(14) yes
C52 . C50 . C51 . 59.36(11) yes
C50 . C53 . C52 . 61.05(11) yes
C50 . C53 . H531 . 118.8 no
C52 . C53 . H531 . 120.3 no
C50 . C53 . H532 . 118.1 no
C52 . C53 . H532 . 118.2 no
H531 . C53 . H532 . 111.9 no
C50 . C52 . C53 . 59.66(11) yes
C50 . C52 . C51 . 59.67(11) yes
C53 . C52 . C51 . 99.37(14) yes
C50 . C52 . C54 . 132.60(14) yes
C53 . C52 . C54 . 128.15(15) yes
C51 . C52 . C54 . 131.35(16) yes
C50 . C51 . C52 . 60.98(11) yes
C50 . C51 . H511 . 118.3 no
C52 . C51 . H511 . 119.2 no
C50 . C51 . H512 . 118.4 no
C52 . C51 . H512 . 118.3 no
H511 . C51 . H512 . 112.6 no
C52 . C54 . C59 . 119.45(15) yes
C52 . C54 . C55 . 121.57(15) yes
C59 . C54 . C55 . 118.96(15) yes
C54 . C59 . C58 . 120.63(17) yes
C54 . C59 . H591 . 120.5 no
C58 . C59 . H591 . 118.8 no
C59 . C58 . C57 . 120.21(16) yes
C59 . C58 . H581 . 119.9 no
C57 . C58 . H581 . 119.9 no
C58 . C57 . C56 . 119.36(16) yes
C58 . C57 . H571 . 120.3 no
C56 . C57 . H571 . 120.4 no
C57 . C56 . C55 . 120.61(17) yes
C57 . C56 . H561 . 119.0 no
C55 . C56 . H561 . 120.4 no
C54 . C55 . C56 . 120.22(16) yes
C54 . C55 . H551 . 120.0 no
C56 . C55 . H551 . 119.8 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
C17 . H171 . O29 . 134 0.94 2.51 3.234(3) yes
C33 . H331 . O28 1_455 134 0.97 2.50 3.257(3) yes
C37 . H371 . O9 1_655 129 0.94 2.54 3.217(3) yes
C53 . H532 . O48 1_455 139 0.97 2.51 3.302(3) yes


####################################################################### 
# 
# 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_18
_database_code_depnum_ccdc_archive 'CCDC 2074463'
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2021-03-31 deposited with the CCDC.	2021-04-27 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2020-03-13
_audit_creation_method           'CRYSTALS_ver_14.61_build_7453 '

_oxford_structure_analysis_title 7304
_chemical_name_systematic        .
_chemical_melting_point          'not measured'


_cell_length_a                   5.91440(10)
_cell_length_b                   16.5154(2)
_cell_length_c                   14.7712(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.2702(14)
_cell_angle_gamma                90
_cell_volume                     1436.73(4)

_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'
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 = C17 H16 O2 S1 
# Dc =      1.31 Fooo =    600.00 Mu =     19.81 M =    284.38
# Found Formula = C17 H16 O2 S1 
# Dc =      1.31 FOOO =    600.00 Mu =     19.81 M =    284.38

_chemical_formula_sum            'C17 H16 O2 S'
_chemical_formula_moiety         'C17 H16 O2 S'
_chemical_compound_source        .
_chemical_formula_weight         284.38


_cell_measurement_reflns_used    7909
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      77.11
_cell_measurement_temperature    150

_exptl_crystal_description       needles
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.08
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_max          0.25

_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    1.981

# Sheldrick geometric approximatio 0.82 0.85 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_T_max  0.85
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_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 (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_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            11872
_diffrn_reflns_av_unetI/netI     0.025
_reflns_number_total             3022
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_av_sigmaI/netI    0.0248
# Number of reflections with Friedels Law is 3022 
# Theoretical number of reflections is about 6082 

_diffrn_reflns_theta_min         4.025
_diffrn_reflns_theta_max         77.086
_diffrn_measured_fraction_theta_max 0.991

_diffrn_reflns_theta_full        75.545
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_reflns_limit_h_min              -7
_reflns_limit_h_max              7
_reflns_limit_k_min              0
_reflns_limit_k_max              20
_reflns_limit_l_min              0
_reflns_limit_l_max              18

_oxford_diffrn_Wilson_B_factor   2.02
_oxford_diffrn_Wilson_scale      0.02

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

_refine_diff_density_min         -0.33
_refine_diff_density_max         0.35


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

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3022
_oxford_refine_ls_R_factor_ref   0.0308
_refine_ls_R_factor_all          0.0308
_refine_ls_wR_factor_ref         0.0820 #Calculated the Oxford way
_refine_ls_wR_factor_all         0.0820
_refine_ls_goodness_of_fit_ref   1.0022
_refine_ls_shift/su_max          0.0005902
_refine_ls_shift/su_mean         0.0000336


# Computed with no filters except I/sigma = -10 
_oxford_reflns_number_all        3022
_oxford_refine_ls_R_factor_all   0.0308
_oxford_refine_ls_wR_factor_all  0.0820

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2881
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_gt          0.0806


_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) + ( 0.05P)² + 0.49P] 
 ,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
C1 C 0.5382(2) 0.27781(7) -0.06551(8) 0.0254 1.0000 Uani . . . . . .
C2 C 0.5655(2) 0.26265(8) -0.15637(9) 0.0313 1.0000 Uani . . . . . .
C3 C 0.3917(3) 0.28093(8) -0.22289(8) 0.0347 1.0000 Uani . . . . . .
C4 C 0.1904(2) 0.31478(8) -0.19943(9) 0.0344 1.0000 Uani . . . . . .
C5 C 0.1600(2) 0.32959(7) -0.10908(9) 0.0274 1.0000 Uani . . . . . .
C6 C 0.33439(19) 0.31050(7) -0.04282(7) 0.0213 1.0000 Uani . . . . . .
S7 S 0.29589(5) 0.328391(16) 0.072523(18) 0.0230 1.0000 Uani . . . . . .
O8 O 0.05579(16) 0.33112(6) 0.08202(7) 0.0340 1.0000 Uani . . . . . .
O9 O 0.43643(18) 0.27225(6) 0.12649(6) 0.0369 1.0000 Uani . . . . . .
C10 C 0.40322(19) 0.42471(7) 0.09221(8) 0.0242 1.0000 Uani . . . . . .
C11 C 0.6379(2) 0.44924(8) 0.12884(9) 0.0318 1.0000 Uani . . . . . .
C12 C 0.44285(19) 0.46730(7) 0.18348(8) 0.0252 1.0000 Uani . . . . . .
C13 C 0.2815(2) 0.50209(7) 0.10944(8) 0.0283 1.0000 Uani . . . . . .
C14 C 0.4064(2) 0.44458(7) 0.27714(8) 0.0247 1.0000 Uani . . . . . .
C15 C 0.2088(2) 0.46685(8) 0.31555(8) 0.0305 1.0000 Uani . . . . . .
C16 C 0.1815(2) 0.44832(9) 0.40555(9) 0.0349 1.0000 Uani . . . . . .
C17 C 0.3499(3) 0.40834(8) 0.46028(9) 0.0335 1.0000 Uani . . . . . .
C18 C 0.5460(3) 0.38636(8) 0.42146(9) 0.0356 1.0000 Uani . . . . . .
C19 C 0.5750(2) 0.40392(8) 0.33145(9) 0.0310 1.0000 Uani . . . . . .
C20 C 0.3235(3) 0.39024(9) 0.55854(9) 0.0468 1.0000 Uani . . . . . .
H11 H 0.6575 0.2660 -0.0198 0.0332 1.0000 Uiso R . . . . .
H21 H 0.7005 0.2387 -0.1717 0.0380 1.0000 Uiso R . . . . .
H31 H 0.4101 0.2690 -0.2846 0.0415 1.0000 Uiso R . . . . .
H41 H 0.0743 0.3266 -0.2436 0.0413 1.0000 Uiso R . . . . .
H51 H 0.0244 0.3515 -0.0924 0.0348 1.0000 Uiso R . . . . .
H111 H 0.7112 0.4937 0.0978 0.0383 1.0000 Uiso R . . . . .
H112 H 0.7398 0.4067 0.1505 0.0373 1.0000 Uiso R . . . . .
H131 H 0.3284 0.5505 0.0790 0.0350 1.0000 Uiso R . . . . .
H132 H 0.1157 0.4996 0.1167 0.0330 1.0000 Uiso R . . . . .
H151 H 0.0904 0.4945 0.2797 0.0378 1.0000 Uiso R . . . . .
H161 H 0.0461 0.4636 0.4304 0.0416 1.0000 Uiso R . . . . .
H181 H 0.6637 0.3585 0.4582 0.0447 1.0000 Uiso R . . . . .
H191 H 0.7115 0.3888 0.3060 0.0374 1.0000 Uiso R . . . . .
H202 H 0.4159 0.3450 0.5781 0.0716 1.0000 Uiso R . . . . .
H203 H 0.3667 0.4359 0.5970 0.0708 1.0000 Uiso R . . . . .
H201 H 0.1678 0.3775 0.5681 0.0706 1.0000 Uiso R . . . . .

_refine_ls_extinction_coef       24(4)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          6.49(16)
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
C1 . C2 . 1.3892(17) yes
C1 . C6 . 1.3898(16) yes
C1 . H11 . 0.950 no
C2 . C3 . 1.3883(19) yes
C2 . H21 . 0.937 no
C3 . C4 . 1.388(2) yes
C3 . H31 . 0.948 no
C4 . C5 . 1.3846(18) yes
C4 . H41 . 0.924 no
C5 . C6 . 1.3912(16) yes
C5 . H51 . 0.934 no
C6 . S7 . 1.7644(11) yes
S7 . O8 . 1.4404(9) yes
S7 . O9 . 1.4367(9) yes
S7 . C10 . 1.7274(12) yes
C10 . C11 . 1.4986(16) yes
C10 . C12 . 1.5197(15) yes
C10 . C13 . 1.4999(16) yes
C11 . C12 . 1.4975(15) yes
C11 . H111 . 0.987 no
C11 . H112 . 0.961 no
C12 . C13 . 1.4983(17) yes
C12 . C14 . 1.4684(16) yes
C13 . H131 . 0.971 no
C13 . H132 . 0.998 no
C14 . C15 . 1.3941(16) yes
C14 . C19 . 1.3939(17) yes
C15 . C16 . 1.3881(18) yes
C15 . H151 . 0.955 no
C16 . C17 . 1.390(2) yes
C16 . H161 . 0.945 no
C17 . C18 . 1.389(2) yes
C17 . C20 . 1.5039(18) yes
C18 . C19 . 1.3868(19) yes
C18 . H181 . 0.959 no
C19 . H191 . 0.954 no
C20 . H202 . 0.955 no
C20 . H203 . 0.964 no
C20 . H201 . 0.967 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 . C1 . C6 . 118.90(11) yes
C2 . C1 . H11 . 120.3 no
C6 . C1 . H11 . 120.8 no
C1 . C2 . C3 . 120.04(12) yes
C1 . C2 . H21 . 119.1 no
C3 . C2 . H21 . 120.9 no
C2 . C3 . C4 . 120.47(12) yes
C2 . C3 . H31 . 119.5 no
C4 . C3 . H31 . 120.0 no
C3 . C4 . C5 . 120.14(12) yes
C3 . C4 . H41 . 120.5 no
C5 . C4 . H41 . 119.3 no
C4 . C5 . C6 . 118.99(11) yes
C4 . C5 . H51 . 120.9 no
C6 . C5 . H51 . 120.1 no
C5 . C6 . C1 . 121.45(11) yes
C5 . C6 . S7 . 119.23(9) yes
C1 . C6 . S7 . 119.32(9) yes
C6 . S7 . O8 . 108.37(6) yes
C6 . S7 . O9 . 107.96(5) yes
O8 . S7 . O9 . 119.44(6) yes
C6 . S7 . C10 . 103.81(5) yes
O8 . S7 . C10 . 107.76(5) yes
O9 . S7 . C10 . 108.42(6) yes
S7 . C10 . C11 . 128.58(9) yes
S7 . C10 . C12 . 126.87(8) yes
C11 . C10 . C12 . 59.49(7) yes
S7 . C10 . C13 . 129.69(9) yes
C11 . C10 . C13 . 98.70(10) yes
C12 . C10 . C13 . 59.49(8) yes
C10 . C11 . C12 . 60.96(7) yes
C10 . C11 . H111 . 117.7 no
C12 . C11 . H111 . 119.7 no
C10 . C11 . H112 . 117.0 no
C12 . C11 . H112 . 117.2 no
H111 . C11 . H112 . 114.2 no
C10 . C12 . C11 . 59.56(7) yes
C10 . C12 . C13 . 59.60(8) yes
C11 . C12 . C13 . 98.82(10) yes
C10 . C12 . C14 . 133.91(10) yes
C11 . C12 . C14 . 130.10(11) yes
C13 . C12 . C14 . 130.31(10) yes
C10 . C13 . C12 . 60.91(8) yes
C10 . C13 . H131 . 117.5 no
C12 . C13 . H131 . 117.7 no
C10 . C13 . H132 . 118.3 no
C12 . C13 . H132 . 118.2 no
H131 . C13 . H132 . 114.2 no
C12 . C14 . C15 . 121.14(11) yes
C12 . C14 . C19 . 120.40(11) yes
C15 . C14 . C19 . 118.37(11) yes
C14 . C15 . C16 . 120.49(12) yes
C14 . C15 . H151 . 120.0 no
C16 . C15 . H151 . 119.5 no
C15 . C16 . C17 . 121.41(12) yes
C15 . C16 . H161 . 119.4 no
C17 . C16 . H161 . 119.2 no
C16 . C17 . C18 . 117.71(12) yes
C16 . C17 . C20 . 121.56(13) yes
C18 . C17 . C20 . 120.73(14) yes
C17 . C18 . C19 . 121.52(12) yes
C17 . C18 . H181 . 118.8 no
C19 . C18 . H181 . 119.7 no
C14 . C19 . C18 . 120.49(12) yes
C14 . C19 . H191 . 119.0 no
C18 . C19 . H191 . 120.5 no
C17 . C20 . H202 . 109.9 no
C17 . C20 . H203 . 111.6 no
H202 . C20 . H203 . 108.7 no
C17 . C20 . H201 . 111.6 no
H202 . C20 . H201 . 108.1 no
H203 . C20 . H201 . 106.7 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
C4 . H41 . O9 3_454 124 0.92 2.59 3.1976(18) yes
C11 . H112 . O8 1_655 134 0.96 2.53 3.2720(18) yes


