# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_hyy-tbu-1
_database_code_depnum_ccdc_archive 'CCDC 1583478'
_audit_update_record             
;
2017-11-01 deposited with the CCDC.
2018-06-20 downloaded from the CCDC.
;
_audit_creation_date             2017-11-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H42 N2 O4 S2'
_chemical_formula_sum            'C44 H42 N2 O4 S2'
_chemical_formula_weight         726.91
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2994(2)
_cell_length_b                   9.0319(3)
_cell_length_c                   14.3088(3)
_cell_angle_alpha                84.935(2)
_cell_angle_beta                 77.163(2)
_cell_angle_gamma                84.614(2)
_cell_volume                     913.49(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    6185
_cell_measurement_temperature    293(2)
_cell_measurement_theta_min      4.9190
_cell_measurement_theta_max      73.6550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.695
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7076
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.072
_diffrn_reflns_theta_max         67.072
_diffrn_reflns_theta_min         4.930
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  53.00   0.50    1.00    --    0.00  57.00  90.00  134
  2  ω     59.00  85.00   0.50    1.00    --    0.00  57.00  90.00   52
  3  ω    -36.00 -11.00   0.50    1.00    --  -98.80  72.00-150.00   50
  4  ω    -45.00 -10.00   0.50    1.00    --  -98.80  57.00-120.00   70
  5  ω    -90.00 -47.00   0.50    1.00    --  -98.80  57.00 120.00   86
  6  ω    -42.00  -9.00   0.50    1.00    --  -98.80  57.00 120.00   66
  7  ω   -103.00 -31.00   0.50    1.00    --  -98.80  19.00   0.00  144
  8  ω   -101.00 -75.00   0.50    1.00    --  -98.80  72.00 -30.00   52
  9  ω   -107.00 -36.00   0.50    1.00    --  -98.80  57.00  30.00  142
 10  ω   -106.00 -80.00   0.50    1.00    --  -98.80  72.00 150.00   52
 11  ω   -114.00 -29.00   0.50    1.00    --  -98.80  72.00 120.00  170
 12  ω   -112.00 -32.00   0.50    1.00    --  -98.80  72.00 -90.00  160
 13  ω   -114.00 -53.00   0.50    1.00    --  -98.80  72.00-150.00  122
 14  ω   -112.00 -21.00   0.50    1.00    --  -98.80  72.00  30.00  182
 15  ω   -109.00 -83.00   0.50    1.00    --  -98.80  57.00-120.00   52
 16  ω   -122.00 -92.00   0.50    1.00    --  -98.80 -38.00  30.00   60
 17  ω   -177.00-141.00   0.50    1.00    --  -98.80 -38.00  30.00   72
 18  ω   -188.00-106.00   0.50    1.00    --  -98.80 -38.00  60.00  164
 19  ω   -184.00 -99.00   0.50    1.00    --  -98.80 -19.00 -60.00  170
 20  ω   -188.00-119.00   0.50    1.00    --  -98.80 -19.00   0.00  138
 21  ω    -42.00  12.00   0.50    1.00    --    0.00 -72.00-120.00  108
 22  ω    -89.00 -64.00   0.50    1.00    --    0.00 -19.00-180.00   50
 23  ω    -86.00 -50.00   0.50    1.00    --    0.00 -72.00-120.00   72
 24  ω    -89.00 -19.00   0.50    1.00    --    0.00 -57.00   0.00  140
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1339336000
_diffrn_orient_matrix_UB_12      -0.0979186000
_diffrn_orient_matrix_UB_13      0.0534504000
_diffrn_orient_matrix_UB_21      0.1177288000
_diffrn_orient_matrix_UB_22      -0.0511317000
_diffrn_orient_matrix_UB_23      -0.0966173000
_diffrn_orient_matrix_UB_31      0.1238299000
_diffrn_orient_matrix_UB_32      0.1315004000
_diffrn_orient_matrix_UB_33      -0.0078103000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3066
_reflns_number_total             3202
_reflns_odcompleteness_completeness 97.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.0081(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0637P)²+0.4352P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1114
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C005(H005), C009(H009), C00A(H00A), C00C(H00C), C00D(H00D), C00E(H00E),
 C00F(H00F), C00G(H00G), C00H(H00H), C00J(H00J), C00M(H00M), C00N(H00N)
2.b Idealised Me refined as rotating group:
 C00O(H00B,H00I,H00K), C00P(H00L,H00O,H00P), C00Q(H00Q,H00R,H00S)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S01 S 0.65840(5) 0.14970(4) 1.05906(3) 0.02402(16) Uani 1 1 d . . . . .
O002 O 0.76866(18) 0.01194(13) 1.07214(9) 0.0320(3) Uani 1 1 d . . . . .
O003 O 0.46433(16) 0.16735(14) 1.10942(9) 0.0305(3) Uani 1 1 d . . . . .
N004 N 0.3469(2) 0.35800(16) 0.78135(10) 0.0288(3) Uani 1 1 d . . . . .
C005 C 0.5085(2) 0.25978(18) 0.90738(12) 0.0240(4) Uani 1 1 d . . . . .
H005 H 0.405731 0.293532 0.953561 0.029 Uiso 1 1 calc R . . . .
C006 C 0.3104(2) 0.33336(19) 0.69021(12) 0.0253(4) Uani 1 1 d . . . . .
C007 C 0.2233(2) 0.70614(18) 0.90902(11) 0.0235(4) Uani 1 1 d . . . . .
C008 C 0.6645(2) 0.18459(17) 0.93489(12) 0.0231(3) Uani 1 1 d . . . . .
C009 C 0.8213(2) 0.13112(18) 0.86826(13) 0.0268(4) Uani 1 1 d . . . . .
H009 H 0.924937 0.080742 0.887805 0.032 Uiso 1 1 calc R . . . .
C00A C 0.3006(2) 0.18963(19) 0.66530(12) 0.0289(4) Uani 1 1 d . . . . .
H00A H 0.311990 0.108869 0.709222 0.035 Uiso 1 1 calc R . . . .
C00B C 0.2414(2) 0.47748(18) 0.83233(11) 0.0246(4) Uani 1 1 d . . . . .
C00C C 0.0276(2) 0.72000(19) 0.92316(12) 0.0262(4) Uani 1 1 d . . . . .
H00C H -0.042763 0.800782 0.952913 0.031 Uiso 1 1 calc R . . . .
C00D C 0.3313(2) 0.58613(18) 0.86448(11) 0.0243(4) Uani 1 1 d . . . . .
H00D H 0.461731 0.578651 0.856321 0.029 Uiso 1 1 calc R . . . .
C00E C 0.0454(2) 0.49027(19) 0.84659(12) 0.0270(4) Uani 1 1 d . . . . .
H00E H -0.015274 0.417658 0.825606 0.032 Uiso 1 1 calc R . . . .
C00F C -0.0595(2) 0.6092(2) 0.89140(12) 0.0285(4) Uani 1 1 d . . . . .
H00F H -0.190108 0.615515 0.900550 0.034 Uiso 1 1 calc R . . . .
C00G C 0.2738(3) 0.1666(2) 0.57491(12) 0.0293(4) Uani 1 1 d . . . . .
H00G H 0.268009 0.069625 0.559198 0.035 Uiso 1 1 calc R . . . .
C00H C 0.6635(2) 0.23105(19) 0.74268(12) 0.0272(4) Uani 1 1 d . . . . .
H00H H 0.664496 0.246400 0.677447 0.033 Uiso 1 1 calc R . . . .
C00I C 0.5066(2) 0.28449(17) 0.81015(12) 0.0242(4) Uani 1 1 d . . . . .
C00J C 0.8167(2) 0.15582(19) 0.77217(13) 0.0291(4) Uani 1 1 d . . . . .
H00J H 0.919227 0.120968 0.726227 0.035 Uiso 1 1 calc R . . . .
C00K C 0.2554(2) 0.28441(19) 0.50664(12) 0.0273(4) Uani 1 1 d . . . . .
C00L C 0.2331(3) 0.2537(2) 0.40604(13) 0.0339(4) Uani 1 1 d . . . . .
C00M C 0.2613(3) 0.4270(2) 0.53434(13) 0.0318(4) Uani 1 1 d . . . . .
H00M H 0.246503 0.508248 0.491284 0.038 Uiso 1 1 calc R . . . .
C00N C 0.2887(3) 0.4518(2) 0.62426(13) 0.0314(4) Uani 1 1 d . . . . .
H00N H 0.292552 0.548780 0.640442 0.038 Uiso 1 1 calc R . . . .
C00O C 0.2396(3) 0.3951(2) 0.33882(13) 0.0363(4) Uani 1 1 d . . . . .
H00B H 0.134860 0.463926 0.363017 0.054 Uiso 1 1 calc GR . . . .
H00I H 0.232801 0.370289 0.275878 0.054 Uiso 1 1 calc GR . . . .
H00K H 0.355227 0.440107 0.335311 0.054 Uiso 1 1 calc GR . . . .
C00P C 0.0426(4) 0.1890(3) 0.41313(17) 0.0512(6) Uani 1 1 d . . . . .
H00L H 0.042494 0.092323 0.446925 0.077 Uiso 1 1 calc GR . . . .
H00O H 0.023171 0.180328 0.349709 0.077 Uiso 1 1 calc GR . . . .
H00P H -0.056815 0.253949 0.447190 0.077 Uiso 1 1 calc GR . . . .
C00Q C 0.3933(4) 0.1426(3) 0.36157(15) 0.0547(6) Uani 1 1 d . . . . .
H00Q H 0.512153 0.180580 0.360793 0.082 Uiso 1 1 calc GR . . . .
H00R H 0.384427 0.128632 0.297026 0.082 Uiso 1 1 calc GR . . . .
H00S H 0.383718 0.048955 0.398967 0.082 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S01 O002 1.4383(12) . ?
S01 O003 1.4407(12) . ?
S01 C007 1.7722(17) 2_667 ?
S01 C008 1.7682(17) . ?
N004 C006 1.428(2) . ?
N004 C00B 1.422(2) . ?
N004 C00I 1.411(2) . ?
C005 H005 0.9300 . ?
C005 C008 1.385(2) . ?
C005 C00I 1.392(2) . ?
C006 C00A 1.388(2) . ?
C006 C00N 1.384(2) . ?
C007 C00C 1.392(2) . ?
C007 C00D 1.393(2) . ?
C008 C009 1.394(2) . ?
C009 H009 0.9300 . ?
C009 C00J 1.381(2) . ?
C00A H00A 0.9300 . ?
C00A C00G 1.386(2) . ?
C00B C00D 1.393(2) . ?
C00B C00E 1.395(2) . ?
C00C H00C 0.9300 . ?
C00C C00F 1.393(2) . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9300 . ?
C00E C00F 1.378(2) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00G C00K 1.398(2) . ?
C00H H00H 0.9300 . ?
C00H C00I 1.401(2) . ?
C00H C00J 1.381(2) . ?
C00J H00J 0.9300 . ?
C00K C00L 1.536(2) . ?
C00K C00M 1.388(2) . ?
C00L C00O 1.528(3) . ?
C00L C00P 1.538(3) . ?
C00L C00Q 1.530(3) . ?
C00M H00M 0.9300 . ?
C00M C00N 1.385(2) . ?
C00N H00N 0.9300 . ?
C00O H00B 0.9600 . ?
C00O H00I 0.9600 . ?
C00O H00K 0.9600 . ?
C00P H00L 0.9600 . ?
C00P H00O 0.9600 . ?
C00P H00P 0.9600 . ?
C00Q H00Q 0.9600 . ?
C00Q H00R 0.9600 . ?
C00Q H00S 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O002 S01 O003 119.89(8) . . ?
O002 S01 C007 107.19(7) . 2_667 ?
O002 S01 C008 107.99(7) . . ?
O003 S01 C007 107.39(8) . 2_667 ?
O003 S01 C008 107.66(7) . . ?
C008 S01 C007 105.92(7) . 2_667 ?
C00B N004 C006 118.07(13) . . ?
C00I N004 C006 119.85(13) . . ?
C00I N004 C00B 120.98(13) . . ?
C008 C005 H005 120.2 . . ?
C008 C005 C00I 119.58(15) . . ?
C00I C005 H005 120.2 . . ?
C00A C006 N004 120.47(15) . . ?
C00N C006 N004 120.68(15) . . ?
C00N C006 C00A 118.83(15) . . ?
C00C C007 S01 119.63(12) . 2_667 ?
C00C C007 C00D 121.87(16) . . ?
C00D C007 S01 118.36(13) . 2_667 ?
C005 C008 S01 118.27(12) . . ?
C005 C008 C009 122.22(15) . . ?
C009 C008 S01 119.46(12) . . ?
C008 C009 H009 121.3 . . ?
C00J C009 C008 117.47(15) . . ?
C00J C009 H009 121.3 . . ?
C006 C00A H00A 120.0 . . ?
C00G C00A C006 119.97(16) . . ?
C00G C00A H00A 120.0 . . ?
C00D C00B N004 120.97(15) . . ?
C00D C00B C00E 119.28(15) . . ?
C00E C00B N004 119.68(15) . . ?
C007 C00C H00C 121.0 . . ?
C007 C00C C00F 118.00(15) . . ?
C00F C00C H00C 121.0 . . ?
C007 C00D H00D 120.4 . . ?
C00B C00D C007 119.17(15) . . ?
C00B C00D H00D 120.4 . . ?
C00B C00E H00E 119.6 . . ?
C00F C00E C00B 120.83(16) . . ?
C00F C00E H00E 119.6 . . ?
C00C C00F H00F 119.6 . . ?
C00E C00F C00C 120.84(16) . . ?
C00E C00F H00F 119.6 . . ?
C00A C00G H00G 119.0 . . ?
C00A C00G C00K 122.07(16) . . ?
C00K C00G H00G 119.0 . . ?
C00I C00H H00H 119.7 . . ?
C00J C00H H00H 119.7 . . ?
C00J C00H C00I 120.60(15) . . ?
C005 C00I N004 120.07(14) . . ?
C005 C00I C00H 118.58(14) . . ?
C00H C00I N004 121.32(15) . . ?
C009 C00J C00H 121.54(15) . . ?
C009 C00J H00J 119.2 . . ?
C00H C00J H00J 119.2 . . ?
C00G C00K C00L 120.43(16) . . ?
C00M C00K C00G 116.68(15) . . ?
C00M C00K C00L 122.88(16) . . ?
C00K C00L C00P 109.79(16) . . ?
C00O C00L C00K 112.11(15) . . ?
C00O C00L C00P 107.84(16) . . ?
C00O C00L C00Q 107.99(17) . . ?
C00Q C00L C00K 109.44(15) . . ?
C00Q C00L C00P 109.62(18) . . ?
C00K C00M H00M 119.0 . . ?
C00N C00M C00K 121.92(16) . . ?
C00N C00M H00M 119.0 . . ?
C006 C00N C00M 120.51(16) . . ?
C006 C00N H00N 119.7 . . ?
C00M C00N H00N 119.7 . . ?
C00L C00O H00B 109.5 . . ?
C00L C00O H00I 109.5 . . ?
C00L C00O H00K 109.5 . . ?
H00B C00O H00I 109.5 . . ?
H00B C00O H00K 109.5 . . ?
H00I C00O H00K 109.5 . . ?
C00L C00P H00L 109.5 . . ?
C00L C00P H00O 109.5 . . ?
C00L C00P H00P 109.5 . . ?
H00L C00P H00O 109.5 . . ?
H00L C00P H00P 109.5 . . ?
H00O C00P H00P 109.5 . . ?
C00L C00Q H00Q 109.5 . . ?
C00L C00Q H00R 109.5 . . ?
C00L C00Q H00S 109.5 . . ?
H00Q C00Q H00R 109.5 . . ?
H00Q C00Q H00S 109.5 . . ?
H00R C00Q H00S 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.749
_oxdiff_exptl_absorpt_empirical_full_min 0.485
####################################################################### 
# 
# 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_hyy-och3-1
_database_code_depnum_ccdc_archive 'CCDC 1583482'
_audit_update_record             
;
2017-11-01 deposited with the CCDC.
2018-06-20 downloaded from the CCDC.
;
_audit_creation_date             2017-11-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C38 H30 N2 O6 S2'
_chemical_formula_sum            'C38 H30 N2 O6 S2'
_chemical_formula_weight         674.76
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.5501(6)
_cell_length_b                   4.9755(2)
_cell_length_c                   23.1851(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.243(4)
_cell_angle_gamma                90
_cell_volume                     1538.19(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3773
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.2530
_cell_measurement_theta_min      4.6620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.021
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.8a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            5881
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.063
_diffrn_reflns_theta_max         67.063
_diffrn_reflns_theta_min         3.314
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00   8.00   0.50    0.50    --    0.00 -38.00-120.00   96
  2  ω    -49.00  11.00   0.50    0.50    --    0.00 -57.00-180.00  120
  3  ω    -47.00 -21.00   0.50    0.59    --  -98.80  38.00 -90.00   52
  4  ω    -69.00 -12.00   0.50    0.59    --  -98.80  57.00 150.00  114
  5  ω     -1.00  38.00   0.50    0.59    --    5.00  72.00  30.00   78
  6  ω     65.00  90.00   0.50    0.59    --    5.00  72.00  30.00   50
  7  ω   -114.00 -50.00   0.50    0.59    --  -98.80  72.00 -90.00  128
  8  ω   -112.00  -9.00   0.50    0.59    --  -98.80  19.00   0.00  206
  9  ω   -108.00 -16.00   0.50    0.59    --  -98.80  19.00 -90.00  184
 10  ω   -113.00 -32.00   0.50    0.59    --  -98.80  72.00   0.00  162
 11  ω   -109.00 -80.00   0.50    0.59    --  -98.80  72.00 -30.00   58
 12  ω   -110.00 -85.00   0.50    0.59    --  -98.80  38.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0973035000
_diffrn_orient_matrix_UB_12      -0.0067048000
_diffrn_orient_matrix_UB_13      0.0458532000
_diffrn_orient_matrix_UB_21      0.0619688000
_diffrn_orient_matrix_UB_22      -0.0126703000
_diffrn_orient_matrix_UB_23      -0.0495684000
_diffrn_orient_matrix_UB_31      0.0046883000
_diffrn_orient_matrix_UB_32      0.3094501000
_diffrn_orient_matrix_UB_33      -0.0010903000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2477
_reflns_number_total             2706
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.8a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.8a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.8a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2706
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0720P)²+0.4530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1190
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4AA(H4AA), C(H), C3(H3), C8AA(H8AA), C9AA(H9AA), C0BA(H0BA), C2BA(H2BA),
 C3BA(H3BA), C4BA(H4BA), C8BA(H8BA), C1(H1), C0AA(H0AA)
2.b Idealised Me refined as rotating group:
 C5AA(H5AA,H5AB,H5AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 0.14610(3) 0.56177(8) 0.43656(2) 0.02432(18) Uani 1 1 d . . . . .
O0AA O 0.21822(10) 0.4520(3) 0.40426(6) 0.0321(3) Uani 1 1 d . . . . .
O O 0.08443(9) 0.3872(2) 0.46398(5) 0.0301(3) Uani 1 1 d . . . . .
O1 O 0.46296(10) 0.9100(3) 0.85427(6) 0.0382(4) Uani 1 1 d . . . . .
N1AA N 0.19865(11) 1.0050(3) 0.64076(6) 0.0294(4) Uani 1 1 d . . . . .
C2AA C 0.21300(12) 0.7758(3) 0.49090(7) 0.0235(4) Uani 1 1 d . . . . .
C3AA C 0.09528(12) 1.0253(4) 0.64344(7) 0.0245(4) Uani 1 1 d . . . . .
C4AA C 0.26266(12) 1.1684(4) 0.73920(7) 0.0274(4) Uani 1 1 d . . . . .
H4AA H 0.215742 1.306465 0.732782 0.033 Uiso 1 1 calc R . . . .
C2 C 0.06705(12) 0.7798(3) 0.38888(7) 0.0236(4) Uani 1 1 d . . . . .
C C -0.04385(13) 0.9166(4) 0.69163(8) 0.0299(4) Uani 1 1 d . . . . .
H H -0.069078 0.821044 0.720284 0.036 Uiso 1 1 calc R . . . .
C3 C 0.03256(12) 1.1903(3) 0.60438(7) 0.0246(4) Uani 1 1 d . . . . .
H3 H 0.056701 1.278793 0.574395 0.030 Uiso 1 1 calc R . . . .
C8AA C 0.30224(13) 0.8908(4) 0.48160(7) 0.0270(4) Uani 1 1 d . . . . .
H8AA H 0.325686 0.862565 0.446749 0.032 Uiso 1 1 calc R . . . .
C9AA C 0.32509(13) 1.1481(4) 0.79329(7) 0.0287(4) Uani 1 1 d . . . . .
H9AA H 0.318964 1.268696 0.823102 0.034 Uiso 1 1 calc R . . . .
C0BA C 0.17608(12) 0.8153(3) 0.54250(7) 0.0247(4) Uani 1 1 d . . . . .
H0BA H 0.115494 0.738817 0.547418 0.030 Uiso 1 1 calc R . . . .
C1BA C 0.39656(13) 0.9470(4) 0.80250(7) 0.0275(4) Uani 1 1 d . . . . .
C2BA C 0.35512(13) 1.0482(4) 0.52549(8) 0.0302(4) Uani 1 1 d . . . . .
H2BA H 0.414661 1.128593 0.519904 0.036 Uiso 1 1 calc R . . . .
C3BA C 0.32104(13) 1.0887(4) 0.57782(8) 0.0286(4) Uani 1 1 d . . . . .
H3BA H 0.358056 1.194247 0.607014 0.034 Uiso 1 1 calc R . . . .
C4BA C 0.34098(13) 0.7869(4) 0.70426(7) 0.0289(4) Uani 1 1 d . . . . .
H4BA H 0.346490 0.664285 0.674723 0.035 Uiso 1 1 calc R . . . .
C6BA C 0.26851(12) 0.9880(4) 0.69454(7) 0.0257(4) Uani 1 1 d . . . . .
C7BA C 0.23147(13) 0.9716(4) 0.58682(7) 0.0248(4) Uani 1 1 d . . . . .
C8BA C 0.40496(13) 0.7689(4) 0.75788(8) 0.0303(4) Uani 1 1 d . . . . .
H8BA H 0.453945 0.635895 0.763873 0.036 Uiso 1 1 calc R . . . .
C1 C 0.05590(13) 0.8858(4) 0.68632(7) 0.0282(4) Uani 1 1 d . . . . .
H1 H 0.096944 0.770849 0.711641 0.034 Uiso 1 1 calc R . . . .
C0AA C -0.10615(13) 1.0878(4) 0.65482(7) 0.0278(4) Uani 1 1 d . . . . .
H0AA H -0.172408 1.113588 0.659153 0.033 Uiso 1 1 calc R . . . .
C5AA C 0.46568(15) 1.1136(5) 0.89741(8) 0.0389(5) Uani 1 1 d . . . . .
H5AA H 0.476868 1.284803 0.880600 0.058 Uiso 1 1 calc GR . . . .
H5AB H 0.519043 1.076794 0.929603 0.058 Uiso 1 1 calc GR . . . .
H5AC H 0.402950 1.116862 0.911203 0.058 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S O0AA 1.4404(13) . ?
S O 1.4303(13) . ?
S C2AA 1.7711(17) . ?
S C2 1.7677(17) . ?
O1 C1BA 1.378(2) . ?
O1 C5AA 1.419(2) . ?
N1AA C3AA 1.417(2) . ?
N1AA C6BA 1.428(2) . ?
N1AA C7BA 1.410(2) . ?
C2AA C8AA 1.389(2) . ?
C2AA C0BA 1.390(2) . ?
C3AA C3 1.394(2) . ?
C3AA C1 1.394(2) . ?
C4AA C9AA 1.386(2) . ?
C4AA C6BA 1.383(2) . ?
C2 C3 1.394(2) 3_576 ?
C2 C0AA 1.390(2) 3_576 ?
C C1 1.387(3) . ?
C C0AA 1.382(3) . ?
C8AA C2BA 1.379(3) . ?
C9AA C1BA 1.383(3) . ?
C0BA C7BA 1.396(2) . ?
C1BA C8BA 1.382(3) . ?
C2BA C3BA 1.388(3) . ?
C3BA C7BA 1.395(2) . ?
C4BA C6BA 1.392(2) . ?
C4BA C8BA 1.386(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O0AA S C2AA 106.81(8) . . ?
O0AA S C2 107.41(8) . . ?
O S O0AA 120.31(8) . . ?
O S C2AA 108.33(8) . . ?
O S C2 108.28(8) . . ?
C2 S C2AA 104.63(8) . . ?
C1BA O1 C5AA 116.72(15) . . ?
C3AA N1AA C6BA 118.24(14) . . ?
C7BA N1AA C3AA 121.17(14) . . ?
C7BA N1AA C6BA 120.20(14) . . ?
C8AA C2AA S 119.14(12) . . ?
C8AA C2AA C0BA 122.13(15) . . ?
C0BA C2AA S 118.69(13) . . ?
C3 C3AA N1AA 120.45(15) . . ?
C3 C3AA C1 119.35(16) . . ?
C1 C3AA N1AA 120.17(16) . . ?
C6BA C4AA C9AA 121.55(16) . . ?
C3 C2 S 119.11(12) 3_576 . ?
C0AA C2 S 118.67(13) 3_576 . ?
C0AA C2 C3 122.22(15) 3_576 3_576 ?
C0AA C C1 120.72(16) . . ?
C3AA C3 C2 118.73(15) . 3_576 ?
C2BA C8AA C2AA 118.15(15) . . ?
C1BA C9AA C4AA 119.36(16) . . ?
C2AA C0BA C7BA 118.90(15) . . ?
O1 C1BA C9AA 124.18(16) . . ?
O1 C1BA C8BA 116.01(15) . . ?
C8BA C1BA C9AA 119.81(16) . . ?
C8AA C2BA C3BA 121.16(16) . . ?
C2BA C3BA C7BA 120.26(16) . . ?
C8BA C4BA C6BA 120.16(16) . . ?
C4AA C6BA N1AA 119.86(16) . . ?
C4AA C6BA C4BA 118.54(16) . . ?
C4BA C6BA N1AA 121.56(16) . . ?
C0BA C7BA N1AA 120.36(15) . . ?
C3BA C7BA N1AA 120.23(16) . . ?
C3BA C7BA C0BA 119.38(15) . . ?
C1BA C8BA C4BA 120.55(16) . . ?
C C1 C3AA 120.71(16) . . ?
C C0AA C2 118.18(16) . 3_576 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.286
_oxdiff_exptl_absorpt_empirical_full_min 0.675
