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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Au-SPhCO2Me
_database_code_depnum_ccdc_archive 'CCDC 1441706'
_audit_update_record             
;
2015-12-10 deposited with the CCDC.
2016-02-18 downloaded from the CCDC.
;


#=============================================================================

# POWDER SPECIMEN AND CRYSTAL DATA

_chemical_formula_sum            'C8 H7 Au O2 S'
_chemical_formula_weight         364.18
_exptl_crystal_colour            Colourless

_cell_length_a                   37.4027(12)
_cell_length_b                   7.01569(12)
_cell_length_c                   6.36593(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1670.454(67)


_cell_formula_units_Z            8
_diffrn_ambient_temperature      293
_cell_measurement_temperature    293
_pd_spec_mounting                'glass capillary'
_pd_spec_mount_mode              transmission
_pd_spec_shape                   cylinder



_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca
loop_
_symmetry_equiv_pos_as_xyz
'-x, -y, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z+1/2'
'x, y, z'
'x+1/2, -y+1/2, -z'
'x+1/2, y, -z+1/2'


#=============================================================================

#  EXPERIMENTAL DATA

_diffrn_source                   'X-ray sealed tube'
_diffrn_radiation_type           'CuKa1 radiation'

_diffrn_radiation_monochromator  'Ge(111) monochromator'
_diffrn_measurement_device_type  'Bruker D8 Advance diffractometer'


#  The following four items give details of the measured (not processed)
#  powder pattern.  Angles are in degrees.

#_pd_meas_number_of_points         9636
_pd_meas_2theta_range_min        2.500
_pd_meas_2theta_range_max        100.00
_pd_meas_2theta_range_inc        0.010119


#=============================================================================


#  REFINEMENT DATA


# Use the next field to give any special details about the fitting of the
# powder pattern.


# The next three items are given as text.

_pd_proc_ls_profile_function     'modified Thompson-Cox-Hastings pseudo-Voigt '
_pd_proc_ls_background_function  'Chebychev polynomial'



#  The following profile R-factors are NOT CORRECTED for background
#  The sum is extended to all non-excluded points.
#  These are the current CIF standard

_pd_proc_ls_prof_R_factor        0.056
_pd_proc_ls_prof_wR_factor       0.076

#  Items related to LS refinement

_refine_ls_R_I_factor            0.038
_refine_ls_goodness_of_fit_all   6.41
_refine_ls_number_reflns         877
_refine_ls_number_structural_parameters 21
_refine_ls_number_profile_parameters 24
_refine_ls_number_restraints     3

# The following four items apply to angular dispersive measurements.
# 2theta minimum, maximum and increment (in degrees) are for the 
# intensities used in the refinement.

_pd_proc_2theta_range_min        3.000
_pd_proc_2theta_range_max        100.000
_pd_proc_2theta_range_inc        0.010
_diffrn_radiation_wavelength     1.5406

_computing_structure_solution    TOPAS
_computing_structure_refinement  TOPAS
_computing_molecular_graphics    DIAMOND

#=============================================================================


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
Au1 Au 8 0.49994(14) 0.27316(15) 0.24162(44) 1 0.005(39)
C11 C 8 0.3536743 0.01716533 -0.01586295 1 3.51(25)
C12 C 8 0.3842028 -0.03883164 -0.1175149 1 3.51(25)
C13 C 8 0.4162541 -0.03836799 -0.01334472 1 3.51(25)
C14 C 8 0.417777 0.01809263 0.1924774 1 3.51(25)
C15 C 8 0.3872485 0.0740896 0.2941293 1 3.51(25)
C16 C 8 0.3551971 0.07362595 0.1899592 1 3.51(25)
C17 C 8 0.3191872 0.01666645 -0.1279495 1 3.51(25)
S18 S 8 0.461058 0.01871872 0.3331451 1 3.51(25)
H12 H 8 0.3831468 -0.07798316 -0.2602383 1 4
H13 H 8 0.4374235 -0.07719801 -0.0838333 1 4
H15 H 8 0.3883045 0.1132411 0.4368527 1 4
H16 H 8 0.3340278 0.112456 0.2604477 1 4
O11 O 8 0.3178712 -0.03246248 -0.3165366 1 3.51(25)
O12 O 8 0.2891144 0.06911291 -0.02722426 1 3.51(25)
C18 C 8 0.2563612 0.06863911 -0.1336755 1 3.51(25)
_chemical_name_systematic        (AuSPhCO2Me)n
_exptl_crystal_description       powder
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1441707'
_audit_update_record             
;
2015-12-10 deposited with the CCDC.
2016-02-18 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   5.9165(4)
_cell_length_b                   7.6653(5)
_cell_length_c                   17.8190(10)
_cell_angle_alpha                79.997(5)
_cell_angle_beta                 85.946(5)
_cell_angle_gamma                75.915(6)
_cell_volume                     771.57(9)

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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
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'
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'


_cell_formula_units_Z            2

# Given Formula = C7.50 H19.50 N10.50 O2 S3 
# Dc =      1.66 Fooo =    348.00 Mu =     46.71 M =    385.00
# Found Formula = C16 H14 O4 S2 
# Dc =      1.44 FOOO =    348.00 Mu =     32.67 M =    334.42

_chemical_formula_sum            'C16 H14 O4 S2'
_chemical_formula_moiety         'C16 H14 O4 S2'
_chemical_compound_source        ?
_chemical_formula_weight         334.42


_cell_measurement_reflns_used    3851
_cell_measurement_theta_min      5.0070
_cell_measurement_theta_max      66.5800
_cell_measurement_temperature    150

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.053
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_max          0.481

_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             348
_exptl_absorpt_coefficient_mu    3.267

# Sheldrick geometric approximatio 0.72 0.84 
_exptl_absorpt_correction_T_min  0.452
_exptl_absorpt_correction_T_max  0.843
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector_area_resol_mean 10.4678
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_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            8184
_reflns_number_total             2691
_diffrn_reflns_av_R_equivalents  0.028
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2691 
# Theoretical number of reflections is about 5466 


_diffrn_reflns_theta_min         5.043
_diffrn_reflns_theta_max         66.700
_diffrn_measured_fraction_theta_max 0.988

_diffrn_reflns_theta_full        66.690
_diffrn_measured_fraction_theta_full 0.988


_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_reflns_limit_h_min              -6
_reflns_limit_h_max              7
_reflns_limit_k_min              -8
_reflns_limit_k_max              9
_reflns_limit_l_min              0
_reflns_limit_l_max              21

_oxford_diffrn_Wilson_B_factor   2.95
_oxford_diffrn_Wilson_scale      0.02

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

_refine_diff_density_min         -0.25
_refine_diff_density_max         0.23


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


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns         2691
_refine_ls_number_restraints     0
_refine_ls_number_parameters     199
_oxford_refine_ls_R_factor_ref   0.0400
_refine_ls_wR_factor_ref         0.0633
_refine_ls_goodness_of_fit_ref   0.9835
_refine_ls_shift/su_max          0.0007521
_refine_ls_shift/su_mean         0.0000309


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2691
_refine_ls_R_factor_all          0.0400
_refine_ls_wR_factor_all         0.0633

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2401
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_gt          0.0605

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


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 845. 0.128E+04 659. 177. 
;

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

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

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


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
S1 S 0.44266(10) 0.61814(8) 0.72937(3) 0.0403 1.0000 Uani . . . . . .
S2 S 0.71835(9) 0.44565(8) 0.78449(3) 0.0394 1.0000 Uani . . . . . .
C3 C 0.6117(3) 0.3684(3) 0.87671(12) 0.0314 1.0000 Uani . . . . . .
C4 C 0.7802(3) 0.2550(3) 0.92514(12) 0.0336 1.0000 Uani . . . . . .
C5 C 0.7183(3) 0.1852(3) 0.99831(12) 0.0344 1.0000 Uani . . . . . .
C6 C 0.4858(3) 0.2266(3) 1.02392(11) 0.0292 1.0000 Uani . . . . . .
C7 C 0.3191(3) 0.3401(3) 0.97508(12) 0.0310 1.0000 Uani . . . . . .
C8 C 0.3798(3) 0.4116(3) 0.90184(12) 0.0336 1.0000 Uani . . . . . .
H81 H 0.2673 0.4885 0.8690 0.0400 1.0000 Uiso R . . . . .
H71 H 0.1625 0.3667 0.9926 0.0371 1.0000 Uiso R . . . . .
C9 C 0.4262(4) 0.1464(3) 1.10247(12) 0.0332 1.0000 Uani . . . . . .
O10 O 0.1951(2) 0.1857(2) 1.11735(8) 0.0379 1.0000 Uani . . . . . .
C11 C 0.1211(4) 0.1094(3) 1.19245(12) 0.0429 1.0000 Uani . . . . . .
H111 H -0.0486 0.1371 1.1943 0.0643 1.0000 Uiso R . . . . .
H113 H 0.1765 0.1608 1.2310 0.0646 1.0000 Uiso R . . . . .
H112 H 0.1788 -0.0244 1.2021 0.0630 1.0000 Uiso R . . . . .
O12 O 0.5667(3) 0.0551(2) 1.14811(9) 0.0469 1.0000 Uani . . . . . .
H51 H 0.8334 0.1095 1.0309 0.0409 1.0000 Uiso R . . . . .
H41 H 0.9349 0.2274 0.9076 0.0397 1.0000 Uiso R . . . . .
C13 C 0.2954(4) 0.4778(3) 0.69129(12) 0.0353 1.0000 Uani . . . . . .
C14 C 0.1233(4) 0.5715(3) 0.64008(12) 0.0384 1.0000 Uani . . . . . .
C15 C -0.0051(4) 0.4758(3) 0.60802(12) 0.0385 1.0000 Uani . . . . . .
C16 C 0.0357(4) 0.2869(3) 0.62744(12) 0.0357 1.0000 Uani . . . . . .
C17 C 0.2065(4) 0.1957(3) 0.67974(12) 0.0376 1.0000 Uani . . . . . .
C18 C 0.3371(4) 0.2905(3) 0.71176(12) 0.0378 1.0000 Uani . . . . . .
H181 H 0.4529 0.2279 0.7474 0.0455 1.0000 Uiso R . . . . .
H171 H 0.2315 0.0658 0.6950 0.0448 1.0000 Uiso R . . . . .
C19 C -0.1010(4) 0.1809(3) 0.59496(13) 0.0401 1.0000 Uani . . . . . .
O20 O -0.2609(3) 0.2868(2) 0.54705(9) 0.0472 1.0000 Uani . . . . . .
C21 C -0.3998(4) 0.1939(4) 0.51210(15) 0.0568 1.0000 Uani . . . . . .
H211 H -0.5061 0.2860 0.4784 0.0852 1.0000 Uiso R . . . . .
H213 H -0.4821 0.1275 0.5508 0.0852 1.0000 Uiso R . . . . .
H212 H -0.2968 0.1083 0.4823 0.0844 1.0000 Uiso R . . . . .
O22 O -0.0718(3) 0.0177(2) 0.60980(11) 0.0582 1.0000 Uani . . . . . .
H151 H -0.1211 0.5375 0.5723 0.0460 1.0000 Uiso R . . . . .
H141 H 0.0925 0.6991 0.6274 0.0456 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0409(3) 0.0351(3) 0.0417(3) -0.0015(2) 0.0035(2) -0.0074(2)
S2 0.0308(3) 0.0453(3) 0.0392(3) -0.0037(2) 0.0066(2) -0.0079(2)
C3 0.0288(11) 0.0310(11) 0.0358(11) -0.0086(9) 0.0025(9) -0.0083(8)
C4 0.0225(10) 0.0383(12) 0.0407(12) -0.0116(9) 0.0030(9) -0.0062(9)
C5 0.0251(10) 0.0369(12) 0.0403(12) -0.0097(9) -0.0040(9) -0.0021(9)
C6 0.0277(10) 0.0286(10) 0.0333(11) -0.0090(8) -0.0007(8) -0.0076(8)
C7 0.0222(10) 0.0335(11) 0.0366(11) -0.0080(9) 0.0024(8) -0.0045(8)
C8 0.0267(11) 0.0351(11) 0.0368(12) -0.0051(9) -0.0034(9) -0.0027(9)
C9 0.0301(11) 0.0328(11) 0.0379(12) -0.0078(9) -0.0019(9) -0.0079(9)
O10 0.0301(8) 0.0450(9) 0.0343(8) -0.0027(7) 0.0046(6) -0.0048(7)
C11 0.0424(13) 0.0458(13) 0.0371(12) -0.0018(10) 0.0081(10) -0.0101(11)
O12 0.0351(9) 0.0579(10) 0.0428(9) 0.0066(8) -0.0072(7) -0.0104(8)
C13 0.0334(11) 0.0367(12) 0.0308(11) -0.0014(9) 0.0077(9) -0.0040(9)
C14 0.0417(13) 0.0298(11) 0.0358(12) 0.0026(9) 0.0052(10) -0.0007(9)
C15 0.0405(12) 0.0358(12) 0.0311(11) 0.0015(9) 0.0016(9) 0.0009(10)
C16 0.0350(12) 0.0351(12) 0.0312(11) -0.0027(9) 0.0060(9) -0.0010(9)
C17 0.0386(12) 0.0302(11) 0.0364(12) 0.0000(9) 0.0049(9) 0.0007(9)
C18 0.0358(12) 0.0367(12) 0.0328(11) 0.0020(9) 0.0013(9) 0.0010(9)
C19 0.0380(12) 0.0419(13) 0.0349(12) -0.0047(10) 0.0083(9) -0.0026(10)
O20 0.0423(9) 0.0496(10) 0.0471(10) -0.0036(8) -0.0054(7) -0.0080(8)
C21 0.0453(15) 0.0761(19) 0.0533(16) -0.0138(14) -0.0018(12) -0.0200(14)
O22 0.0675(12) 0.0376(10) 0.0680(12) -0.0072(9) -0.0101(10) -0.0084(9)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          7.92(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 . S2 . 2.0246(8) yes
S1 . C13 . 1.781(2) yes
S2 . C3 . 1.774(2) yes
C3 . C4 . 1.391(3) yes
C3 . C8 . 1.391(3) yes
C4 . C5 . 1.380(3) yes
C4 . H41 . 0.932 no
C5 . C6 . 1.396(3) yes
C5 . H51 . 0.940 no
C6 . C7 . 1.389(3) yes
C6 . C9 . 1.482(3) yes
C7 . C8 . 1.383(3) yes
C7 . H71 . 0.941 no
C8 . H81 . 0.936 no
C9 . O10 . 1.344(2) yes
C9 . O12 . 1.207(2) yes
O10 . C11 . 1.447(2) yes
C11 . H111 . 0.974 no
C11 . H113 . 0.962 no
C11 . H112 . 0.987 no
C13 . C14 . 1.390(3) yes
C13 . C18 . 1.383(3) yes
C14 . C15 . 1.386(3) yes
C14 . H141 . 0.940 no
C15 . C16 . 1.393(3) yes
C15 . H151 . 0.949 no
C16 . C17 . 1.394(3) yes
C16 . C19 . 1.483(3) yes
C17 . C18 . 1.389(3) yes
C17 . H171 . 0.963 no
C18 . H181 . 0.948 no
C19 . O20 . 1.335(3) yes
C19 . O22 . 1.205(3) yes
O20 . C21 . 1.442(3) yes
C21 . H211 . 0.972 no
C21 . H213 . 0.961 no
C21 . H212 . 0.982 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
S2 . S1 . C13 . 105.75(7) yes
S1 . S2 . C3 . 106.21(7) yes
S2 . C3 . C4 . 114.78(15) yes
S2 . C3 . C8 . 125.17(16) yes
C4 . C3 . C8 . 120.05(19) yes
C3 . C4 . C5 . 120.18(19) yes
C3 . C4 . H41 . 119.1 no
C5 . C4 . H41 . 120.7 no
C4 . C5 . C6 . 120.25(19) yes
C4 . C5 . H51 . 119.7 no
C6 . C5 . H51 . 120.1 no
C5 . C6 . C7 . 119.06(19) yes
C5 . C6 . C9 . 118.53(18) yes
C7 . C6 . C9 . 122.41(18) yes
C6 . C7 . C8 . 121.08(18) yes
C6 . C7 . H71 . 118.6 no
C8 . C7 . H71 . 120.3 no
C3 . C8 . C7 . 119.38(19) yes
C3 . C8 . H81 . 119.6 no
C7 . C8 . H81 . 121.0 no
C6 . C9 . O10 . 112.11(17) yes
C6 . C9 . O12 . 124.58(19) yes
O10 . C9 . O12 . 123.3(2) yes
C9 . O10 . C11 . 115.74(16) yes
O10 . C11 . H111 . 107.8 no
O10 . C11 . H113 . 110.6 no
H111 . C11 . H113 . 110.1 no
O10 . C11 . H112 . 111.0 no
H111 . C11 . H112 . 108.0 no
H113 . C11 . H112 . 109.3 no
S1 . C13 . C14 . 114.81(17) yes
S1 . C13 . C18 . 124.32(17) yes
C14 . C13 . C18 . 120.8(2) yes
C13 . C14 . C15 . 119.6(2) yes
C13 . C14 . H141 . 120.6 no
C15 . C14 . H141 . 119.8 no
C14 . C15 . C16 . 120.4(2) yes
C14 . C15 . H151 . 120.6 no
C16 . C15 . H151 . 119.0 no
C15 . C16 . C17 . 119.2(2) yes
C15 . C16 . C19 . 121.7(2) yes
C17 . C16 . C19 . 119.1(2) yes
C16 . C17 . C18 . 120.8(2) yes
C16 . C17 . H171 . 119.7 no
C18 . C17 . H171 . 119.5 no
C17 . C18 . C13 . 119.2(2) yes
C17 . C18 . H181 . 120.5 no
C13 . C18 . H181 . 120.3 no
C16 . C19 . O20 . 112.4(2) yes
C16 . C19 . O22 . 124.1(2) yes
O20 . C19 . O22 . 123.5(2) yes
C19 . O20 . C21 . 115.9(2) yes
O20 . C21 . H211 . 107.3 no
O20 . C21 . H213 . 109.9 no
H211 . C21 . H213 . 111.7 no
O20 . C21 . H212 . 109.1 no
H211 . C21 . H212 . 109.7 no
H213 . C21 . H212 . 109.1 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
C14 . H141 . O22 1_565 166.45(7) 0.940 2.372 3.293(3) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 12/02/13 at 13:52:56
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 113,X'S) H   ( 112,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) H   ( 213,X'S) H   ( 212,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 12/02/13 at 13:52:56
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_chemical_name_systematic        (SPhCO2Me)2
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
