# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_151228_tyn306_3rd
_database_code_depnum_ccdc_archive 'CCDC 1447653'
_audit_update_record             
;
2016-01-15 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;
_audit_creation_date             2015-12-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H16 Al Br O2 S'
_chemical_formula_sum            'C15 H16 Al Br O2 S'
_chemical_formula_weight         367.23
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 O2 s1 Al1 Br1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   8.0842(5)
_cell_length_b                   12.4461(8)
_cell_length_c                   16.7654(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1686.88(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2960
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4673
_cell_measurement_theta_min      2.9986
_exptl_absorpt_coefficient_mu    2.610
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11251
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.00
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0652661000
_diffrn_orient_matrix_UB_12      -0.0124823000
_diffrn_orient_matrix_UB_13      0.0266940000
_diffrn_orient_matrix_UB_21      0.0441722000
_diffrn_orient_matrix_UB_22      0.0249432000
_diffrn_orient_matrix_UB_23      0.0315441000
_diffrn_orient_matrix_UB_31      -0.0385521000
_diffrn_orient_matrix_UB_32      0.0496902000
_diffrn_orient_matrix_UB_33      -0.0091088000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2327
_reflns_number_total             3071
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack (1983), 1296 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.017(12)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.827
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3071
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0381
_refine_ls_restrained_S_all      0.827
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1249
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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:
 C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br1 Br 0.33766(8) 0.68925(5) 0.12796(3) 0.0796(2) Uani 1 d . . .
S1 S 0.26269(15) 0.72498(10) 0.45801(7) 0.0610(3) Uani 1 d . . .
Al1 Al 0.05243(19) 0.58436(12) 0.35056(9) 0.0622(4) Uani 1 d . . .
O1 O 0.0955(4) 0.6708(3) 0.43868(19) 0.0667(9) Uani 1 d . . .
O2 O 0.2309(4) 0.6216(3) 0.29410(17) 0.0598(8) Uani 1 d . . .
C1 C 0.3140(5) 0.7135(4) 0.2958(3) 0.0521(10) Uani 1 d . . .
C2 C 0.3831(5) 0.7574(4) 0.2255(3) 0.0563(11) Uani 1 d . . .
C3 C 0.4771(7) 0.8488(5) 0.2288(4) 0.0767(15) Uani 1 d . . .
H3 H 0.5228 0.8755 0.1819 0.092 Uiso 1 calc . . R
C4 C 0.5056(8) 0.9016(5) 0.2983(4) 0.0843(19) Uani 1 d . . .
H4 H 0.5709 0.9631 0.2988 0.101 Uiso 1 calc . . R
C5 C 0.4375(7) 0.8635(4) 0.3677(4) 0.0726(14) Uani 1 d . . .
H5 H 0.4529 0.9006 0.4153 0.087 Uiso 1 calc . . R
C6 C 0.3452(6) 0.7691(4) 0.3665(3) 0.0586(10) Uani 1 d . . .
C7 C 0.3969(5) 0.6187(4) 0.4865(3) 0.0536(11) Uani 1 d . . .
C8 C 0.5006(6) 0.5653(4) 0.4359(3) 0.0636(13) Uani 1 d . . .
H8 H 0.5040 0.5832 0.3821 0.076 Uiso 1 calc . . R
C9 C 0.6004(6) 0.4843(4) 0.4653(3) 0.0670(13) Uani 1 d . . .
H9 H 0.6724 0.4490 0.4309 0.080 Uiso 1 calc . . R
C10 C 0.5959(6) 0.4543(4) 0.5450(3) 0.0638(12) Uani 1 d . . .
C11 C 0.4928(7) 0.5111(5) 0.5948(3) 0.0794(16) Uani 1 d . . .
H11 H 0.4887 0.4936 0.6487 0.095 Uiso 1 calc . . R
C12 C 0.3958(6) 0.5932(5) 0.5666(3) 0.0709(14) Uani 1 d . . .
H12 H 0.3292 0.6318 0.6016 0.085 Uiso 1 calc . . R
C13 C 0.7012(9) 0.3652(5) 0.5745(4) 0.097(2) Uani 1 d . . .
H13A H 0.7539 0.3865 0.6233 0.146 Uiso 1 calc . . GR
H13B H 0.7839 0.3485 0.5354 0.146 Uiso 1 calc . . GR
H13C H 0.6338 0.3029 0.5840 0.146 Uiso 1 calc . . GR
C14 C -0.1509(7) 0.6410(6) 0.3047(3) 0.0874(17) Uani 1 d . . .
H14A H -0.1247 0.6976 0.2679 0.131 Uiso 1 calc . . GR
H14B H -0.2199 0.6689 0.3465 0.131 Uiso 1 calc . . GR
H14C H -0.2084 0.5846 0.2772 0.131 Uiso 1 calc . . GR
C15 C 0.0724(9) 0.4331(5) 0.3809(5) 0.103(2) Uani 1 d . . .
H15A H 0.0377 0.3885 0.3372 0.154 Uiso 1 calc . . GR
H15B H 0.0039 0.4191 0.4265 0.154 Uiso 1 calc . . GR
H15C H 0.1856 0.4173 0.3938 0.154 Uiso 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
Br1 C2 1.878(5) . ?
S1 O1 1.545(4) . ?
S1 C6 1.760(5) . ?
S1 C7 1.776(5) . ?
Al1 O1 1.860(4) . ?
Al1 O2 1.786(3) . ?
Al1 C14 1.947(6) . ?
Al1 C15 1.957(6) . ?
O2 C1 1.328(5) . ?
C1 C2 1.414(6) . ?
C1 C6 1.396(6) . ?
C2 C3 1.369(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.357(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.392(7) . ?
C7 C8 1.366(6) . ?
C7 C12 1.380(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.382(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.387(7) . ?
C10 C11 1.376(7) . ?
C10 C13 1.483(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.372(7) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
O1 S1 C6 106.6(2) . . ?
O1 S1 C7 105.4(2) . . ?
C6 S1 C7 103.6(2) . . ?
O1 Al1 C14 105.2(2) . . ?
O1 Al1 C15 109.5(3) . . ?
O2 Al1 O1 96.87(15) . . ?
O2 Al1 C14 112.3(2) . . ?
O2 Al1 C15 108.7(2) . . ?
C14 Al1 C15 121.4(3) . . ?
S1 O1 Al1 125.66(18) . . ?
C1 O2 Al1 128.4(3) . . ?
O2 C1 C2 121.0(4) . . ?
O2 C1 C6 122.4(4) . . ?
C6 C1 C2 116.5(4) . . ?
C1 C2 Br1 118.3(3) . . ?
C3 C2 Br1 121.2(4) . . ?
C3 C2 C1 120.4(5) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 122.1(5) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.5(5) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.7(5) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 S1 121.2(3) . . ?
C5 C6 S1 117.0(4) . . ?
C5 C6 C1 121.8(5) . . ?
C8 C7 S1 124.8(4) . . ?
C8 C7 C12 119.8(5) . . ?
C12 C7 S1 115.4(4) . . ?
C7 C8 H8 120.3 . . ?
C7 C8 C9 119.4(5) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 H9 119.2 . . ?
C8 C9 C10 121.7(5) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 C13 120.5(5) . . ?
C11 C10 C9 117.5(5) . . ?
C11 C10 C13 122.0(5) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.3(5) . . ?
C12 C11 H11 119.3 . . ?
C7 C12 H12 119.9 . . ?
C11 C12 C7 120.2(5) . . ?
C11 C12 H12 119.9 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Al1 C14 H14A 109.5 . . ?
Al1 C14 H14B 109.5 . . ?
Al1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
Al1 C15 H15A 109.5 . . ?
Al1 C15 H15B 109.5 . . ?
Al1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C2 C3 C4 177.3(5) . . . . ?
S1 C7 C8 C9 179.5(4) . . . . ?
S1 C7 C12 C11 178.9(4) . . . . ?
Al1 O2 C1 C2 -143.6(4) . . . . ?
Al1 O2 C1 C6 39.7(6) . . . . ?
O1 S1 C6 C1 -31.4(5) . . . . ?
O1 S1 C6 C5 146.3(4) . . . . ?
O1 S1 C7 C8 93.0(4) . . . . ?
O1 S1 C7 C12 -89.0(4) . . . . ?
O1 Al1 O2 C1 -28.4(4) . . . . ?
O2 Al1 O1 S1 -15.3(3) . . . . ?
O2 C1 C2 Br1 5.7(6) . . . . ?
O2 C1 C2 C3 -176.0(4) . . . . ?
O2 C1 C6 S1 -4.7(7) . . . . ?
O2 C1 C6 C5 177.7(4) . . . . ?
C1 C2 C3 C4 -1.0(8) . . . . ?
C2 C1 C6 S1 178.6(3) . . . . ?
C2 C1 C6 C5 0.9(7) . . . . ?
C2 C3 C4 C5 -0.7(9) . . . . ?
C3 C4 C5 C6 2.4(9) . . . . ?
C4 C5 C6 S1 179.7(4) . . . . ?
C4 C5 C6 C1 -2.6(8) . . . . ?
C6 S1 O1 Al1 38.8(3) . . . . ?
C6 S1 C7 C8 -18.7(5) . . . . ?
C6 S1 C7 C12 159.3(4) . . . . ?
C6 C1 C2 Br1 -177.5(3) . . . . ?
C6 C1 C2 C3 0.8(7) . . . . ?
C7 S1 O1 Al1 -70.8(3) . . . . ?
C7 S1 C6 C1 79.5(4) . . . . ?
C7 S1 C6 C5 -102.7(4) . . . . ?
C7 C8 C9 C10 1.2(8) . . . . ?
C8 C7 C12 C11 -3.0(8) . . . . ?
C8 C9 C10 C11 -2.5(8) . . . . ?
C8 C9 C10 C13 178.4(5) . . . . ?
C9 C10 C11 C12 1.1(8) . . . . ?
C10 C11 C12 C7 1.7(9) . . . . ?
C12 C7 C8 C9 1.6(7) . . . . ?
C13 C10 C11 C12 -179.9(5) . . . . ?
C14 Al1 O1 S1 -130.6(3) . . . . ?
C14 Al1 O2 C1 81.1(4) . . . . ?
C15 Al1 O1 S1 97.4(3) . . . . ?
C15 Al1 O2 C1 -141.8(4) . . . . ?

####################################################################### 
# 
# 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_151125_tyn0288
_database_code_depnum_ccdc_archive 'CCDC 1447654'
_audit_update_record             
;
2016-01-15 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;
_audit_creation_date             2015-11-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H22 O3 S'
_chemical_formula_sum            'C18 H22 O3 S'
_chemical_formula_weight         318.42
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8 S1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   8.2836(9)
_cell_length_b                   10.3728(11)
_cell_length_c                   19.708(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.303(12)
_cell_angle_gamma                90.00
_cell_volume                     1693.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1841
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5551
_cell_measurement_theta_min      3.1413
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.36
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6680
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.15
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0673524000
_diffrn_orient_matrix_UB_12      -0.0421520000
_diffrn_orient_matrix_UB_13      -0.0006638000
_diffrn_orient_matrix_UB_21      0.0453297000
_diffrn_orient_matrix_UB_22      -0.0461759000
_diffrn_orient_matrix_UB_23      -0.0180412000
_diffrn_orient_matrix_UB_31      0.0272364000
_diffrn_orient_matrix_UB_32      -0.0277738000
_diffrn_orient_matrix_UB_33      0.0311346000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2386
_reflns_number_total             3259
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.112
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.103
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.13(16)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         3259
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0801
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1388P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1990
_refine_ls_wR_factor_ref         0.2265
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C29(H29A,H29B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C22(H22), C23(H23), C24(H24), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C),
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C30(H30A,H30B,
 H30C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.0988(2) 0.14123(15) 0.16011(10) 0.0527(6) Uani 1 d . . .
O1 O 0.1253(8) 0.0225(6) 0.2019(3) 0.0791(18) Uani 1 d . . .
O2 O 0.1809(5) 0.4199(4) 0.1208(2) 0.0454(10) Uani 1 d . . .
O3 O 0.1447(7) 0.5695(5) 0.2078(2) 0.0596(14) Uani 1 d . . .
C1 C 0.2968(7) 0.2157(6) 0.1563(3) 0.0438(15) Uani 1 d . . .
C2 C 0.3136(6) 0.3449(6) 0.1396(3) 0.0376(14) Uani 1 d . . .
C3 C 0.4692(7) 0.4012(7) 0.1388(3) 0.0434(15) Uani 1 d . . .
C4 C 0.5996(7) 0.3225(8) 0.1585(3) 0.0533(18) Uani 1 d . . .
H4 H 0.7032 0.3572 0.1587 0.064 Uiso 1 calc . . R
C5 C 0.5807(9) 0.1969(8) 0.1775(4) 0.0596(19) Uani 1 d . . .
H5 H 0.6699 0.1484 0.1913 0.071 Uiso 1 calc . . R
C6 C 0.4262(8) 0.1409(7) 0.1760(3) 0.0545(17) Uani 1 d . . .
H6 H 0.4120 0.0550 0.1881 0.065 Uiso 1 calc . . R
C7 C 0.0707(8) 0.0815(7) 0.0713(3) 0.0536(17) Uani 1 d . . .
C8 C -0.0873(9) 0.0068(8) 0.0735(5) 0.080(3) Uani 1 d . . .
H8A H -0.0767 -0.0625 0.1056 0.120 Uiso 1 calc . . GR
H8B H -0.1125 -0.0277 0.0293 0.120 Uiso 1 calc . . GR
H8C H -0.1725 0.0635 0.0869 0.120 Uiso 1 calc . . GR
C9 C 0.0591(12) 0.1959(8) 0.0243(4) 0.081(3) Uani 1 d . . .
H9A H -0.0311 0.2485 0.0365 0.121 Uiso 1 calc . . GR
H9B H 0.0443 0.1664 -0.0216 0.121 Uiso 1 calc . . GR
H9C H 0.1566 0.2456 0.0281 0.121 Uiso 1 calc . . GR
C10 C 0.2075(9) -0.0072(7) 0.0536(4) 0.066(2) Uani 1 d . . .
H10A H 0.3044 0.0424 0.0484 0.099 Uiso 1 calc . . GR
H10B H 0.1815 -0.0511 0.0119 0.099 Uiso 1 calc . . GR
H10C H 0.2239 -0.0692 0.0893 0.099 Uiso 1 calc . . GR
C11 C 0.0844(8) 0.4651(7) 0.1759(4) 0.0574(18) Uani 1 d . . .
H11A H -0.0229 0.4854 0.1583 0.069 Uiso 1 calc . . R
H11B H 0.0740 0.3961 0.2087 0.069 Uiso 1 calc . . R
C12 C 0.1213(10) 0.6858(6) 0.1680(4) 0.062(2) Uani 1 d . . .
H12A H 0.1795 0.6787 0.1266 0.092 Uiso 1 calc . . GR
H12B H 0.1606 0.7587 0.1934 0.092 Uiso 1 calc . . GR
H12C H 0.0084 0.6969 0.1576 0.092 Uiso 1 calc . . GR
C13 C 0.4959(7) 0.5351(6) 0.1205(3) 0.0427(14) Uani 1 d . . .
C14 C 0.4424(8) 0.5845(7) 0.0583(3) 0.0539(18) Uani 1 d . . .
H14 H 0.3842 0.5316 0.0286 0.065 Uiso 1 calc . . R
C15 C 0.4738(8) 0.7107(8) 0.0398(4) 0.0596(19) Uani 1 d . . .
H15 H 0.4390 0.7417 -0.0023 0.072 Uiso 1 calc . . R
C16 C 0.5573(9) 0.7898(8) 0.0846(4) 0.067(2) Uani 1 d . . .
H16 H 0.5760 0.8753 0.0729 0.080 Uiso 1 calc . . R
C17 C 0.6121(10) 0.7447(9) 0.1449(4) 0.072(2) Uani 1 d . . .
H17 H 0.6707 0.7984 0.1742 0.087 Uiso 1 calc . . R
C18 C 0.5820(9) 0.6208(9) 0.1632(4) 0.063(2) Uani 1 d . . .
H18 H 0.6196 0.5917 0.2053 0.076 Uiso 1 calc . . R
S2 S 0.9059(2) 0.41057(15) 0.34623(8) 0.0485(5) Uani 1 d . . .
O4 O 0.8896(7) 0.2955(5) 0.3004(3) 0.0697(15) Uani 1 d . . .
O5 O 0.8147(5) 0.6863(4) 0.3802(2) 0.0427(10) Uani 1 d A . .
O6 O 0.8283(7) 0.8288(5) 0.2887(2) 0.0687(16) Uani 1 d A 1 .
C19 C 0.7062(7) 0.4806(7) 0.3487(3) 0.0447(14) Uani 1 d . . .
C20 C 0.6821(7) 0.6086(6) 0.3630(3) 0.0393(13) Uani 1 d . . .
C21 C 0.5272(7) 0.6609(7) 0.3628(3) 0.0440(14) Uani 1 d . . .
C22 C 0.4009(8) 0.5799(7) 0.3444(3) 0.0526(17) Uani 1 d . . .
H22 H 0.2964 0.6129 0.3437 0.063 Uiso 1 calc . . R
C23 C 0.4228(9) 0.4541(8) 0.3272(4) 0.060(2) Uani 1 d . . .
H23 H 0.3348 0.4038 0.3138 0.072 Uiso 1 calc . . R
C24 C 0.5759(8) 0.4012(7) 0.3297(3) 0.0536(16) Uani 1 d . . .
H24 H 0.5922 0.3150 0.3189 0.064 Uiso 1 calc . . R
C25 C 0.9301(7) 0.3477(6) 0.4336(3) 0.0462(15) Uani 1 d . . .
C26 C 0.7965(9) 0.2534(7) 0.4495(4) 0.0620(19) Uani 1 d . . .
H26A H 0.6946 0.2975 0.4482 0.093 Uiso 1 calc . . GR
H26B H 0.8154 0.2178 0.4939 0.093 Uiso 1 calc . . GR
H26C H 0.7949 0.1853 0.4165 0.093 Uiso 1 calc . . GR
C27 C 1.0902(8) 0.2745(9) 0.4326(5) 0.077(2) Uani 1 d . . .
H27A H 1.0825 0.2056 0.4002 0.116 Uiso 1 calc . . GR
H27B H 1.1136 0.2397 0.4769 0.116 Uiso 1 calc . . GR
H27C H 1.1751 0.3323 0.4202 0.116 Uiso 1 calc . . GR
C28 C 0.9357(11) 0.4598(8) 0.4813(4) 0.073(2) Uani 1 d . . .
H28A H 1.0141 0.5211 0.4664 0.110 Uiso 1 calc . . GR
H28B H 0.9652 0.4303 0.5261 0.110 Uiso 1 calc . . GR
H28C H 0.8313 0.5000 0.4821 0.110 Uiso 1 calc . . GR
C29 C 0.9029(9) 0.7333(7) 0.3226(4) 0.0560(18) Uani 1 d . . .
H29A H 1.0080 0.7636 0.3384 0.067 Uiso 1 calc A . R
H29B H 0.9204 0.6623 0.2916 0.067 Uiso 1 calc A . R
C30 C 0.8481(12) 0.9503(8) 0.3204(5) 0.080(3) Uani 1 d . . .
H30A H 0.7901 1.0145 0.2946 0.121 Uiso 1 calc A . GR
H30B H 0.9607 0.9722 0.3226 0.121 Uiso 1 calc A . GR
H30C H 0.8068 0.9467 0.3654 0.121 Uiso 1 calc A . GR
C31 C 0.4951(7) 0.7978(6) 0.3792(3) 0.0443(15) Uani 1 d . . .
C32 C 0.5548(7) 0.8518(7) 0.4397(3) 0.0461(15) Uani 1 d . . .
H32 H 0.6178 0.8015 0.4690 0.055 Uiso 1 calc . . R
C33 C 0.5228(8) 0.9769(7) 0.4570(4) 0.0559(17) Uani 1 d . . .
H33 H 0.5623 1.0102 0.4979 0.067 Uiso 1 calc . . R
C34 C 0.4308(9) 1.0542(8) 0.4130(4) 0.069(2) Uani 1 d . . .
H34 H 0.4108 1.1401 0.4236 0.083 Uiso 1 calc . . R
C35 C 0.3707(10) 1.0015(9) 0.3541(4) 0.069(2) Uani 1 d . . .
H35 H 0.3064 1.0520 0.3254 0.083 Uiso 1 calc . . R
C36 C 0.4016(8) 0.8785(8) 0.3363(3) 0.058(2) Uani 1 d . . .
H36 H 0.3607 0.8467 0.2953 0.069 Uiso 1 calc . . R


_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
S1 O1 1.494(6) . ?
S1 C1 1.816(6) . ?
S1 C7 1.866(7) . ?
O2 C2 1.390(7) . ?
O2 C11 1.441(8) . ?
O3 C11 1.343(9) . ?
O3 C12 1.450(8) . ?
C1 C2 1.387(9) . ?
C1 C6 1.373(9) . ?
C2 C3 1.416(8) . ?
C3 C4 1.402(9) . ?
C3 C13 1.453(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.366(11) . ?
C5 H5 0.9300 . ?
C5 C6 1.405(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.523(10) . ?
C7 C9 1.508(10) . ?
C7 C10 1.506(10) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.391(9) . ?
C13 C18 1.407(10) . ?
C14 H14 0.9300 . ?
C14 C15 1.385(11) . ?
C15 H15 0.9300 . ?
C15 C16 1.379(11) . ?
C16 H16 0.9300 . ?
C16 C17 1.348(11) . ?
C17 H17 0.9300 . ?
C17 C18 1.359(13) . ?
C18 H18 0.9300 . ?
S2 O4 1.501(5) . ?
S2 C19 1.809(6) . ?
S2 C25 1.847(6) . ?
O5 C20 1.398(7) . ?
O5 C29 1.448(8) . ?
O6 C29 1.338(9) . ?
O6 C30 1.414(10) . ?
C19 C20 1.372(9) . ?
C19 C24 1.402(9) . ?
C20 C21 1.394(8) . ?
C21 C22 1.384(9) . ?
C21 C31 1.481(10) . ?
C22 H22 0.9300 . ?
C22 C23 1.362(11) . ?
C23 H23 0.9300 . ?
C23 C24 1.382(10) . ?
C24 H24 0.9300 . ?
C25 C26 1.515(9) . ?
C25 C27 1.528(9) . ?
C25 C28 1.496(9) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 C32 1.399(9) . ?
C31 C36 1.410(9) . ?
C32 H32 0.9300 . ?
C32 C33 1.369(10) . ?
C33 H33 0.9300 . ?
C33 C34 1.394(11) . ?
C34 H34 0.9300 . ?
C34 C35 1.368(12) . ?
C35 H35 0.9300 . ?
C35 C36 1.349(13) . ?
C36 H36 0.9300 . ?

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
O1 S1 C1 104.6(3) . . ?
O1 S1 C7 104.8(4) . . ?
C1 S1 C7 101.3(3) . . ?
C2 O2 C11 115.5(5) . . ?
C11 O3 C12 111.9(6) . . ?
C2 C1 S1 121.1(5) . . ?
C6 C1 S1 116.6(5) . . ?
C6 C1 C2 122.1(6) . . ?
O2 C2 C3 118.8(5) . . ?
C1 C2 O2 121.4(5) . . ?
C1 C2 C3 119.8(6) . . ?
C2 C3 C13 122.7(6) . . ?
C4 C3 C2 116.9(6) . . ?
C4 C3 C13 120.3(6) . . ?
C3 C4 H4 118.7 . . ?
C5 C4 C3 122.6(6) . . ?
C5 C4 H4 118.7 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0(6) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 118.5(7) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
C8 C7 S1 103.4(5) . . ?
C9 C7 S1 108.7(5) . . ?
C9 C7 C8 112.0(6) . . ?
C10 C7 S1 110.0(5) . . ?
C10 C7 C8 110.3(6) . . ?
C10 C7 C9 112.1(7) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 H11A 108.7 . . ?
O2 C11 H11B 108.7 . . ?
O3 C11 O2 114.1(6) . . ?
O3 C11 H11A 108.7 . . ?
O3 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C3 121.6(6) . . ?
C14 C13 C18 116.1(6) . . ?
C18 C13 C3 122.2(6) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 C13 121.5(6) . . ?
C15 C14 H14 119.2 . . ?
C14 C15 H15 120.4 . . ?
C16 C15 C14 119.2(7) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.9(7) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.1(7) . . ?
C18 C17 H17 120.0 . . ?
C13 C18 H18 118.9 . . ?
C17 C18 C13 122.2(7) . . ?
C17 C18 H18 118.9 . . ?
O4 S2 C19 105.4(3) . . ?
O4 S2 C25 106.6(3) . . ?
C19 S2 C25 101.3(3) . . ?
C20 O5 C29 114.4(5) . . ?
C29 O6 C30 113.1(6) . . ?
C20 C19 S2 122.1(5) . . ?
C20 C19 C24 120.6(6) . . ?
C24 C19 S2 117.1(5) . . ?
C19 C20 O5 119.4(5) . . ?
C19 C20 C21 121.0(6) . . ?
C21 C20 O5 119.6(5) . . ?
C20 C21 C31 122.9(6) . . ?
C22 C21 C20 117.0(6) . . ?
C22 C21 C31 120.1(6) . . ?
C21 C22 H22 118.6 . . ?
C23 C22 C21 122.9(7) . . ?
C23 C22 H22 118.6 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 120.0(6) . . ?
C24 C23 H23 120.0 . . ?
C19 C24 H24 120.8 . . ?
C23 C24 C19 118.5(7) . . ?
C23 C24 H24 120.8 . . ?
C26 C25 S2 110.9(4) . . ?
C26 C25 C27 108.7(6) . . ?
C27 C25 S2 103.9(5) . . ?
C28 C25 S2 108.2(5) . . ?
C28 C25 C26 112.5(6) . . ?
C28 C25 C27 112.3(6) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O5 C29 H29A 108.8 . . ?
O5 C29 H29B 108.8 . . ?
O6 C29 O5 113.9(6) . . ?
O6 C29 H29A 108.8 . . ?
O6 C29 H29B 108.8 . . ?
H29A C29 H29B 107.7 . . ?
C32 C31 C21 120.5(6) . . ?
C32 C31 C36 116.9(7) . . ?
C36 C31 C21 122.5(6) . . ?
C31 C32 H32 119.2 . . ?
C33 C32 C31 121.7(6) . . ?
C33 C32 H32 119.2 . . ?
C32 C33 H33 120.1 . . ?
C32 C33 C34 119.9(7) . . ?
C34 C33 H33 120.1 . . ?
C33 C34 H34 120.7 . . ?
C35 C34 C33 118.7(7) . . ?
C35 C34 H34 120.7 . . ?
C34 C35 H35 118.9 . . ?
C36 C35 C34 122.2(7) . . ?
C36 C35 H35 118.9 . . ?
C31 C36 H36 119.6 . . ?
C35 C36 C31 120.7(7) . . ?
C35 C36 H36 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C2 O2 -4.3(8) . . . . ?
S1 C1 C2 C3 178.3(4) . . . . ?
S1 C1 C6 C5 -176.5(5) . . . . ?
O1 S1 C1 C2 -160.6(5) . . . . ?
O1 S1 C1 C6 14.2(6) . . . . ?
O1 S1 C7 C8 66.3(6) . . . . ?
O1 S1 C7 C9 -174.6(6) . . . . ?
O1 S1 C7 C10 -51.6(6) . . . . ?
O2 C2 C3 C4 179.5(5) . . . . ?
O2 C2 C3 C13 1.2(8) . . . . ?
C1 S1 C7 C8 174.9(5) . . . . ?
C1 S1 C7 C9 -66.0(6) . . . . ?
C1 S1 C7 C10 57.0(6) . . . . ?
C1 C2 C3 C4 -3.0(8) . . . . ?
C1 C2 C3 C13 178.8(5) . . . . ?
C2 O2 C11 O3 80.7(7) . . . . ?
C2 C1 C6 C5 -1.7(10) . . . . ?
C2 C3 C4 C5 0.4(10) . . . . ?
C2 C3 C13 C14 -56.7(8) . . . . ?
C2 C3 C13 C18 125.7(7) . . . . ?
C3 C4 C5 C6 1.6(11) . . . . ?
C3 C13 C14 C15 -177.3(6) . . . . ?
C3 C13 C18 C17 177.5(7) . . . . ?
C4 C3 C13 C14 125.1(7) . . . . ?
C4 C3 C13 C18 -52.5(9) . . . . ?
C4 C5 C6 C1 -1.0(11) . . . . ?
C6 C1 C2 O2 -178.9(5) . . . . ?
C6 C1 C2 C3 3.7(9) . . . . ?
C7 S1 C1 C2 90.6(5) . . . . ?
C7 S1 C1 C6 -94.6(5) . . . . ?
C11 O2 C2 C1 78.8(7) . . . . ?
C11 O2 C2 C3 -103.7(6) . . . . ?
C12 O3 C11 O2 75.0(7) . . . . ?
C13 C3 C4 C5 178.7(6) . . . . ?
C13 C14 C15 C16 -1.3(11) . . . . ?
C14 C13 C18 C17 -0.3(11) . . . . ?
C14 C15 C16 C17 1.9(12) . . . . ?
C15 C16 C17 C18 -1.7(13) . . . . ?
C16 C17 C18 C13 0.9(13) . . . . ?
C18 C13 C14 C15 0.5(10) . . . . ?
S2 C19 C20 O5 -3.9(8) . . . . ?
S2 C19 C20 C21 178.2(4) . . . . ?
S2 C19 C24 C23 -176.2(5) . . . . ?
O4 S2 C19 C20 -154.9(5) . . . . ?
O4 S2 C19 C24 19.7(6) . . . . ?
O4 S2 C25 C26 -52.4(5) . . . . ?
O4 S2 C25 C27 64.2(5) . . . . ?
O4 S2 C25 C28 -176.3(5) . . . . ?
O5 C20 C21 C22 179.0(5) . . . . ?
O5 C20 C21 C31 0.9(8) . . . . ?
C19 S2 C25 C26 57.7(5) . . . . ?
C19 S2 C25 C27 174.3(5) . . . . ?
C19 S2 C25 C28 -66.2(5) . . . . ?
C19 C20 C21 C22 -3.1(9) . . . . ?
C19 C20 C21 C31 178.8(5) . . . . ?
C20 O5 C29 O6 75.2(7) . . . . ?
C20 C19 C24 C23 -1.5(9) . . . . ?
C20 C21 C22 C23 0.3(10) . . . . ?
C20 C21 C31 C32 -53.6(8) . . . . ?
C20 C21 C31 C36 127.9(7) . . . . ?
C21 C22 C23 C24 1.9(11) . . . . ?
C21 C31 C32 C33 -178.0(6) . . . . ?
C21 C31 C36 C35 177.8(7) . . . . ?
C22 C21 C31 C32 128.4(7) . . . . ?
C22 C21 C31 C36 -50.1(9) . . . . ?
C22 C23 C24 C19 -1.3(10) . . . . ?
C24 C19 C20 O5 -178.3(5) . . . . ?
C24 C19 C20 C21 3.8(9) . . . . ?
C25 S2 C19 C20 94.1(5) . . . . ?
C25 S2 C19 C24 -91.3(5) . . . . ?
C29 O5 C20 C19 81.7(7) . . . . ?
C29 O5 C20 C21 -100.4(6) . . . . ?
C30 O6 C29 O5 79.8(8) . . . . ?
C31 C21 C22 C23 178.4(6) . . . . ?
C31 C32 C33 C34 -1.1(10) . . . . ?
C32 C31 C36 C35 -0.8(10) . . . . ?
C32 C33 C34 C35 1.8(11) . . . . ?
C33 C34 C35 C36 -2.1(13) . . . . ?
C34 C35 C36 C31 1.6(12) . . . . ?
C36 C31 C32 C33 0.5(9) . . . . ?

####################################################################### 
# 
# 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_151030_tyn0278
_database_code_depnum_ccdc_archive 'CCDC 1447655'
_audit_update_record             
;
2016-01-15 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;
_audit_creation_date             2015-10-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C26 H24 O3 S'
_chemical_formula_sum            'C26 H24 O3 S'
_chemical_formula_weight         416.51
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8 S1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   10.6640(7)
_cell_length_b                   9.2330(6)
_cell_length_c                   11.3470(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.158(6)
_cell_angle_gamma                90.00
_cell_volume                     1110.79(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1627
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3500
_cell_measurement_theta_min      2.8451
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95366
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.26
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4821
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         2.85
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0169796000
_diffrn_orient_matrix_UB_12      0.0202308000
_diffrn_orient_matrix_UB_13      0.0564480000
_diffrn_orient_matrix_UB_21      -0.0587866000
_diffrn_orient_matrix_UB_22      0.0259631000
_diffrn_orient_matrix_UB_23      -0.0269917000
_diffrn_orient_matrix_UB_31      -0.0270119000
_diffrn_orient_matrix_UB_32      -0.0694027000
_diffrn_orient_matrix_UB_33      0.0064277000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1835
_reflns_number_total             2153
_reflns_odcompleteness_completeness 99.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(10)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         2153
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0420
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0532P)²+0.0142P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.1015
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C11(H11), C13(H13), C17(H17), C18(H18),
 C19(H19), C22(H22), C23(H23), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C15(H15A,H15B,H15C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.12661(8) 0.16947(10) 0.06458(8) 0.0502(3) Uani 1 d . . .
O1 O 0.1026(2) 0.0816(3) -0.0456(2) 0.0662(8) Uani 1 d . . .
O2 O 0.2660(2) 0.3066(2) 0.2696(2) 0.0522(6) Uani 1 d . . .
O3 O 0.3243(3) 0.5146(3) 0.1703(3) 0.0775(9) Uani 1 d . . .
C1 C 0.0379(3) 0.0864(4) 0.1729(3) 0.0435(8) Uani 1 d . . .
C2 C -0.0066(3) 0.1692(5) 0.2592(3) 0.0546(9) Uani 1 d . . .
H2 H 0.0131 0.2672 0.2652 0.065 Uiso 1 calc . . R
C3 C -0.0818(3) 0.1054(5) 0.3383(4) 0.0605(10) Uani 1 d . . .
H3 H -0.1123 0.1619 0.3968 0.073 Uiso 1 calc . . R
C4 C -0.1118(3) -0.0390(4) 0.3314(3) 0.0550(9) Uani 1 d . . .
C5 C -0.0671(4) -0.1203(4) 0.2424(4) 0.0601(10) Uani 1 d . . .
H5 H -0.0874 -0.2182 0.2360 0.072 Uiso 1 calc . . R
C6 C 0.0070(3) -0.0596(4) 0.1629(3) 0.0546(9) Uani 1 d . . .
H6 H 0.0360 -0.1157 0.1034 0.066 Uiso 1 calc . . R
C7 C -0.1917(5) -0.1050(6) 0.4192(5) 0.0815(14) Uani 1 d . . .
H7A H -0.2359 -0.1875 0.3840 0.122 Uiso 1 calc . . GR
H7B H -0.2514 -0.0347 0.4408 0.122 Uiso 1 calc . . GR
H7C H -0.1386 -0.1349 0.4886 0.122 Uiso 1 calc . . GR
C8 C 0.2835(3) 0.1217(3) 0.1278(3) 0.0415(8) Uani 1 d . . .
C9 C 0.3402(3) 0.2013(3) 0.2235(3) 0.0425(8) Uani 1 d . . .
C10 C 0.4624(3) 0.1686(4) 0.2706(3) 0.0459(7) Uani 1 d . . .
C11 C 0.5251(3) 0.0584(4) 0.2154(3) 0.0497(9) Uani 1 d . . .
H11 H 0.6083 0.0384 0.2438 0.060 Uiso 1 calc . . R
C12 C 0.4694(3) -0.0228(4) 0.1200(3) 0.0486(8) Uani 1 d . . .
C13 C 0.3462(3) 0.0104(4) 0.0778(3) 0.0471(8) Uani 1 d . . .
H13 H 0.3053 -0.0427 0.0154 0.057 Uiso 1 calc . . R
C14 C 0.3166(4) 0.4511(4) 0.2780(4) 0.0590(10) Uani 1 d . . .
H14A H 0.2638 0.5104 0.3231 0.071 Uiso 1 calc . . R
H14B H 0.4001 0.4480 0.3211 0.071 Uiso 1 calc . . R
C15 C 0.2082(7) 0.5676(7) 0.1146(7) 0.150(3) Uani 1 d . . .
H15A H 0.2010 0.5443 0.0317 0.225 Uiso 1 calc . . GR
H15B H 0.2049 0.6708 0.1242 0.225 Uiso 1 calc . . GR
H15C H 0.1398 0.5237 0.1502 0.225 Uiso 1 calc . . GR
C16 C 0.5233(3) 0.2323(4) 0.3853(3) 0.0452(8) Uani 1 d . . .
C17 C 0.4770(3) 0.1998(4) 0.4889(3) 0.0485(8) Uani 1 d . . .
H17 H 0.4034 0.1453 0.4864 0.058 Uiso 1 calc . . R
C18 C 0.5353(4) 0.2446(4) 0.5994(3) 0.0549(9) Uani 1 d . . .
H18 H 0.5007 0.2205 0.6687 0.066 Uiso 1 calc . . R
C19 C 0.6449(4) 0.3250(4) 0.6040(3) 0.0548(9) Uani 1 d . . .
H19 H 0.6860 0.3531 0.6768 0.066 Uiso 1 calc . . R
C20 C 0.6947(3) 0.3648(3) 0.4980(3) 0.0440(8) Uani 1 d . . .
C21 C 0.6317(3) 0.3191(4) 0.3874(3) 0.0460(8) Uani 1 d . . .
C22 C 0.6802(3) 0.3711(4) 0.2809(3) 0.0536(9) Uani 1 d . . .
H22 H 0.6401 0.3460 0.2069 0.064 Uiso 1 calc . . R
C23 C 0.7847(4) 0.4569(4) 0.2890(4) 0.0630(11) Uani 1 d . . .
H23 H 0.8140 0.4914 0.2200 0.076 Uiso 1 calc . . R
C24 C 0.8486(4) 0.4943(5) 0.3985(5) 0.0699(12) Uani 1 d . . .
H24 H 0.9214 0.5501 0.4017 0.084 Uiso 1 calc . . R
C25 C 0.8054(4) 0.4499(4) 0.4996(4) 0.0603(10) Uani 1 d . . .
H25 H 0.8490 0.4756 0.5719 0.072 Uiso 1 calc . . R
C26 C 0.5394(4) -0.1445(5) 0.0678(4) 0.0729(12) Uani 1 d . . .
H26A H 0.4829 -0.2242 0.0490 0.109 Uiso 1 calc . . GR
H26B H 0.6078 -0.1755 0.1241 0.109 Uiso 1 calc . . GR
H26C H 0.5722 -0.1116 -0.0031 0.109 Uiso 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
S1 O1 1.489(3) . ?
S1 C1 1.801(4) . ?
S1 C8 1.803(3) . ?
O2 C9 1.390(4) . ?
O2 C14 1.438(4) . ?
O3 C14 1.366(5) . ?
O3 C15 1.416(6) . ?
C1 C2 1.366(5) . ?
C1 C6 1.390(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.397(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.371(6) . ?
C4 C5 1.383(5) . ?
C4 C7 1.507(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(5) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.395(4) . ?
C8 C13 1.381(5) . ?
C9 C10 1.387(4) . ?
C10 C11 1.402(5) . ?
C10 C16 1.510(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.396(5) . ?
C12 C13 1.384(5) . ?
C12 C26 1.505(5) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.356(5) . ?
C16 C21 1.405(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.402(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.382(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.413(5) . ?
C20 C21 1.423(4) . ?
C20 C25 1.416(5) . ?
C21 C22 1.446(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.362(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.395(6) . ?
C24 H24 0.9300 . ?
C24 C25 1.345(6) . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 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
O1 S1 C1 106.58(16) . . ?
O1 S1 C8 105.64(16) . . ?
C1 S1 C8 99.08(14) . . ?
C9 O2 C14 116.7(3) . . ?
C14 O3 C15 114.5(4) . . ?
C2 C1 S1 119.9(3) . . ?
C2 C1 C6 120.2(4) . . ?
C6 C1 S1 119.6(3) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.5(4) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.3(4) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 118.3(4) . . ?
C3 C4 C7 120.0(4) . . ?
C5 C4 C7 121.8(4) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.5(4) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 H6 120.4 . . ?
C5 C6 C1 119.2(4) . . ?
C5 C6 H6 120.4 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 S1 119.1(2) . . ?
C13 C8 S1 119.2(2) . . ?
C13 C8 C9 121.6(3) . . ?
O2 C9 C8 116.4(3) . . ?
C10 C9 O2 123.8(3) . . ?
C10 C9 C8 119.7(3) . . ?
C9 C10 C11 117.3(3) . . ?
C9 C10 C16 123.1(3) . . ?
C11 C10 C16 119.1(3) . . ?
C10 C11 H11 118.2 . . ?
C12 C11 C10 123.6(3) . . ?
C12 C11 H11 118.2 . . ?
C11 C12 C26 121.2(3) . . ?
C13 C12 C11 117.3(3) . . ?
C13 C12 C26 121.4(3) . . ?
C8 C13 C12 120.4(3) . . ?
C8 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
O2 C14 H14A 108.9 . . ?
O2 C14 H14B 108.9 . . ?
O3 C14 O2 113.4(3) . . ?
O3 C14 H14A 108.9 . . ?
O3 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C10 119.8(3) . . ?
C17 C16 C21 119.2(3) . . ?
C21 C16 C10 120.9(3) . . ?
C16 C17 H17 118.6 . . ?
C16 C17 C18 122.8(3) . . ?
C18 C17 H17 118.6 . . ?
C17 C18 H18 120.5 . . ?
C19 C18 C17 119.0(4) . . ?
C19 C18 H18 120.5 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.1(3) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C21 119.3(3) . . ?
C19 C20 C25 121.5(3) . . ?
C25 C20 C21 119.3(3) . . ?
C16 C21 C20 119.6(3) . . ?
C16 C21 C22 122.9(3) . . ?
C20 C21 C22 117.5(3) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 120.0(4) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.3 . . ?
C22 C23 C24 121.4(4) . . ?
C24 C23 H23 119.3 . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.3(4) . . ?
C25 C24 H24 119.8 . . ?
C20 C25 H25 119.3 . . ?
C24 C25 C20 121.3(4) . . ?
C24 C25 H25 119.3 . . ?
C12 C26 H26A 109.5 . . ?
C12 C26 H26B 109.5 . . ?
C12 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C2 C3 176.1(3) . . . . ?
S1 C1 C6 C5 -176.3(3) . . . . ?
S1 C8 C9 O2 4.8(4) . . . . ?
S1 C8 C9 C10 -178.0(3) . . . . ?
S1 C8 C13 C12 176.1(3) . . . . ?
O1 S1 C1 C2 -150.4(3) . . . . ?
O1 S1 C1 C6 24.8(3) . . . . ?
O1 S1 C8 C9 171.1(3) . . . . ?
O1 S1 C8 C13 -6.8(3) . . . . ?
O2 C9 C10 C11 179.3(3) . . . . ?
O2 C9 C10 C16 7.0(5) . . . . ?
C1 S1 C8 C9 -78.7(3) . . . . ?
C1 S1 C8 C13 103.3(3) . . . . ?
C1 C2 C3 C4 0.2(6) . . . . ?
C2 C1 C6 C5 -1.1(5) . . . . ?
C2 C3 C4 C5 -1.0(6) . . . . ?
C2 C3 C4 C7 179.1(3) . . . . ?
C3 C4 C5 C6 0.8(6) . . . . ?
C4 C5 C6 C1 0.3(5) . . . . ?
C6 C1 C2 C3 0.9(5) . . . . ?
C7 C4 C5 C6 -179.4(4) . . . . ?
C8 S1 C1 C2 100.2(3) . . . . ?
C8 S1 C1 C6 -84.6(3) . . . . ?
C8 C9 C10 C11 2.4(5) . . . . ?
C8 C9 C10 C16 -170.0(3) . . . . ?
C9 O2 C14 O3 68.1(4) . . . . ?
C9 C8 C13 C12 -1.8(5) . . . . ?
C9 C10 C11 C12 -2.9(5) . . . . ?
C9 C10 C16 C17 65.3(5) . . . . ?
C9 C10 C16 C21 -118.1(4) . . . . ?
C10 C11 C12 C13 1.0(5) . . . . ?
C10 C11 C12 C26 -177.1(4) . . . . ?
C10 C16 C17 C18 174.2(3) . . . . ?
C10 C16 C21 C20 -173.3(3) . . . . ?
C10 C16 C21 C22 9.8(5) . . . . ?
C11 C10 C16 C17 -106.9(4) . . . . ?
C11 C10 C16 C21 69.7(5) . . . . ?
C11 C12 C13 C8 1.3(5) . . . . ?
C13 C8 C9 O2 -177.3(3) . . . . ?
C13 C8 C9 C10 -0.2(5) . . . . ?
C14 O2 C9 C8 -125.9(3) . . . . ?
C14 O2 C9 C10 57.1(4) . . . . ?
C15 O3 C14 O2 77.8(5) . . . . ?
C16 C10 C11 C12 169.8(3) . . . . ?
C16 C17 C18 C19 -0.2(5) . . . . ?
C16 C21 C22 C23 178.9(3) . . . . ?
C17 C16 C21 C20 3.3(5) . . . . ?
C17 C16 C21 C22 -173.6(3) . . . . ?
C17 C18 C19 C20 1.9(5) . . . . ?
C18 C19 C20 C21 -0.9(5) . . . . ?
C18 C19 C20 C25 178.6(3) . . . . ?
C19 C20 C21 C16 -1.7(5) . . . . ?
C19 C20 C21 C22 175.4(3) . . . . ?
C19 C20 C25 C24 -176.2(4) . . . . ?
C20 C21 C22 C23 1.9(5) . . . . ?
C21 C16 C17 C18 -2.4(5) . . . . ?
C21 C20 C25 C24 3.3(5) . . . . ?
C21 C22 C23 C24 1.3(6) . . . . ?
C22 C23 C24 C25 -2.3(7) . . . . ?
C23 C24 C25 C20 0.0(6) . . . . ?
C25 C20 C21 C16 178.8(3) . . . . ?
C25 C20 C21 C22 -4.1(5) . . . . ?
C26 C12 C13 C8 179.4(3) . . . . ?

####################################################################### 
# 
# 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_150914_tyn0245b
_database_code_depnum_ccdc_archive 'CCDC 1447656'
_audit_update_record             
;
2016-01-15 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;
_audit_creation_date             2015-09-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13 H11 Br O2 S'
_chemical_formula_sum            'C13 H11 Br O2 S'
_chemical_formula_weight         311.19
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Br2 C30 H20 s8 O10'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   9.1301(4)
_cell_length_b                   10.8900(6)
_cell_length_c                   13.3698(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1329.31(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2832
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4358
_cell_measurement_theta_min      2.9056
_exptl_absorpt_coefficient_mu    3.236
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8502
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         2.91
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0584624000
_diffrn_orient_matrix_UB_12      -0.0416553000
_diffrn_orient_matrix_UB_13      -0.0085827000
_diffrn_orient_matrix_UB_21      -0.0060554000
_diffrn_orient_matrix_UB_22      0.0212931000
_diffrn_orient_matrix_UB_23      -0.0499210000
_diffrn_orient_matrix_UB_31      0.0507776000
_diffrn_orient_matrix_UB_32      -0.0454003000
_diffrn_orient_matrix_UB_33      -0.0156562000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2012
_reflns_number_total             2418
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack (1983), 1008 Friedel pairs'
_refine_ls_abs_structure_Flack   0.006(10)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2418
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0334
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0300P)²+0.3701P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0677
_refine_ls_wR_factor_ref         0.0737
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br1 Br 0.91328(5) 0.35267(5) 0.81562(4) 0.0855(2) Uani 1 d . . .
S1 S 0.44057(8) 0.63586(7) 0.68717(7) 0.0437(2) Uani 1 d . . .
O1 O 0.4240(3) 0.74121(19) 0.61563(19) 0.0562(6) Uani 1 d . . .
O2 O 0.5948(2) 0.46475(19) 0.81321(19) 0.0509(6) Uani 1 d . . .
H2 H 0.6220 0.3972 0.8329 0.076 Uiso 1 calc . . GR
C1 C 0.6849(3) 0.5041(3) 0.7398(3) 0.0395(8) Uani 1 d . . .
C2 C 0.8308(4) 0.4705(3) 0.7283(3) 0.0472(9) Uani 1 d . . .
C3 C 0.9149(4) 0.5198(4) 0.6537(3) 0.0604(10) Uani 1 d . . .
H3 H 1.0122 0.4957 0.6474 0.073 Uiso 1 calc . . R
C4 C 0.8583(4) 0.6042(3) 0.5882(3) 0.0587(10) Uani 1 d . . .
H4 H 0.9165 0.6372 0.5378 0.070 Uiso 1 calc . . R
C5 C 0.7126(4) 0.6399(3) 0.5981(3) 0.0487(9) Uani 1 d . . .
H5 H 0.6729 0.6980 0.5549 0.058 Uiso 1 calc . . R
C6 C 0.6279(3) 0.5886(3) 0.6722(2) 0.0376(7) Uani 1 d . . .
C7 C 0.3514(3) 0.5084(3) 0.6273(3) 0.0398(8) Uani 1 d . . .
C8 C 0.3137(3) 0.4063(3) 0.6823(3) 0.0512(9) Uani 1 d . . .
H8 H 0.3353 0.4025 0.7502 0.061 Uiso 1 calc . . R
C9 C 0.2432(4) 0.3091(3) 0.6357(4) 0.0598(11) Uani 1 d . . .
H9 H 0.2188 0.2397 0.6725 0.072 Uiso 1 calc . . R
C10 C 0.2091(4) 0.3143(4) 0.5358(4) 0.0623(12) Uani 1 d . . .
C11 C 0.2438(4) 0.4181(4) 0.4826(4) 0.0704(12) Uani 1 d . . .
H11 H 0.2196 0.4230 0.4151 0.085 Uiso 1 calc . . R
C12 C 0.3147(4) 0.5160(4) 0.5285(3) 0.0571(10) Uani 1 d . . .
H12 H 0.3370 0.5864 0.4921 0.069 Uiso 1 calc . . R
C13 C 0.1327(6) 0.2067(4) 0.4850(5) 0.1022(19) Uani 1 d . . .
H13A H 0.1913 0.1341 0.4922 0.153 Uiso 1 calc . . GR
H13B H 0.1199 0.2246 0.4152 0.153 Uiso 1 calc . . GR
H13C H 0.0387 0.1937 0.5154 0.153 Uiso 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
Br1 C2 1.891(3) . ?
S1 O1 1.501(2) . ?
S1 C6 1.798(3) . ?
S1 C7 1.797(3) . ?
O2 H2 0.8200 . ?
O2 C1 1.350(4) . ?
C1 C2 1.390(4) . ?
C1 C6 1.391(4) . ?
C2 C3 1.368(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.371(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.392(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(4) . ?
C7 C8 1.377(5) . ?
C7 C12 1.365(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.386(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.372(6) . ?
C10 C11 1.373(6) . ?
C10 C13 1.523(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.390(5) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
O1 S1 C6 104.10(15) . . ?
O1 S1 C7 105.12(16) . . ?
C7 S1 C6 99.23(13) . . ?
C1 O2 H2 109.5 . . ?
O2 C1 C2 125.5(3) . . ?
O2 C1 C6 117.0(3) . . ?
C2 C1 C6 117.4(3) . . ?
C1 C2 Br1 119.4(3) . . ?
C3 C2 Br1 119.5(3) . . ?
C3 C2 C1 121.0(3) . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.2(4) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.1(4) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.5(3) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 S1 118.2(2) . . ?
C5 C6 S1 119.9(3) . . ?
C5 C6 C1 121.8(3) . . ?
C8 C7 S1 120.0(3) . . ?
C12 C7 S1 119.7(3) . . ?
C12 C7 C8 120.3(3) . . ?
C7 C8 H8 120.3 . . ?
C7 C8 C9 119.5(4) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.8(4) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C11 119.0(4) . . ?
C9 C10 C13 120.5(4) . . ?
C11 C10 C13 120.5(4) . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.7(4) . . ?
C12 C11 H11 119.7 . . ?
C7 C12 C11 119.7(4) . . ?
C7 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C2 C3 C4 179.1(3) . . . . ?
S1 C7 C8 C9 179.2(3) . . . . ?
S1 C7 C12 C11 -179.1(3) . . . . ?
O1 S1 C6 C1 170.2(2) . . . . ?
O1 S1 C6 C5 -7.0(3) . . . . ?
O1 S1 C7 C8 -163.5(2) . . . . ?
O1 S1 C7 C12 13.1(3) . . . . ?
O2 C1 C2 Br1 4.1(5) . . . . ?
O2 C1 C2 C3 -177.1(3) . . . . ?
O2 C1 C6 S1 -0.9(4) . . . . ?
O2 C1 C6 C5 176.2(3) . . . . ?
C1 C2 C3 C4 0.3(6) . . . . ?
C2 C1 C6 S1 -178.7(2) . . . . ?
C2 C1 C6 C5 -1.6(5) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C3 C4 C5 C6 -1.0(5) . . . . ?
C4 C5 C6 S1 178.9(3) . . . . ?
C4 C5 C6 C1 1.8(5) . . . . ?
C6 S1 C7 C8 89.1(3) . . . . ?
C6 S1 C7 C12 -94.3(3) . . . . ?
C6 C1 C2 Br1 -178.3(2) . . . . ?
C6 C1 C2 C3 0.5(5) . . . . ?
C7 S1 C6 C1 -81.5(3) . . . . ?
C7 S1 C6 C5 101.3(3) . . . . ?
C7 C8 C9 C10 -0.8(5) . . . . ?
C8 C7 C12 C11 -2.4(5) . . . . ?
C8 C9 C10 C11 -1.0(6) . . . . ?
C8 C9 C10 C13 179.5(3) . . . . ?
C9 C10 C11 C12 1.1(6) . . . . ?
C10 C11 C12 C7 0.6(6) . . . . ?
C12 C7 C8 C9 2.5(5) . . . . ?
C13 C10 C11 C12 -179.4(4) . . . . ?

####################################################################### 
# 
# 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_160226_tyn322_2
_database_code_depnum_ccdc_archive 'CCDC 1462873'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;
_audit_creation_date             2016-02-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C30 H30 O6 S2'
_chemical_formula_sum            'C30 H30 O6 S2'
_chemical_formula_weight         550.66
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8 S1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z'

_cell_length_a                   13.3030(11)
_cell_length_b                   10.8154(10)
_cell_length_c                   10.2401(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.676(11)
_cell_angle_gamma                90.00
_cell_volume                     1387.3(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1004
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3834
_cell_measurement_theta_min      3.2208
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.28
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2692
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.23
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0439251000
_diffrn_orient_matrix_UB_12      0.0378950000
_diffrn_orient_matrix_UB_13      -0.0016699000
_diffrn_orient_matrix_UB_21      0.0179110000
_diffrn_orient_matrix_UB_22      0.0005867000
_diffrn_orient_matrix_UB_23      0.0735385000
_diffrn_orient_matrix_UB_31      0.0309321000
_diffrn_orient_matrix_UB_32      0.0535171000
_diffrn_orient_matrix_UB_33      0.0003837000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1176
_reflns_number_total             1336
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.16(13)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         1336
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0383
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0596P)²+0.1782P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.1005
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.19044(6) 0.16373(10) 0.41542(10) 0.0530(3) Uani 1 d . . .
O1 O 0.07879(19) 0.1962(3) 0.3295(4) 0.0711(9) Uani 1 d . . .
O2 O 0.41763(16) 0.2074(2) 0.5762(2) 0.0425(6) Uani 1 d . . .
O3 O 0.4466(2) 0.1529(4) 0.8013(3) 0.0704(8) Uani 1 d . . .
C1 C 0.4420(2) 0.3916(3) 0.4573(3) 0.0378(7) Uani 1 d . . .
C2 C 0.3964(3) 0.4822(3) 0.3577(4) 0.0449(8) Uani 1 d . . .
H2 H 0.4380 0.5471 0.3452 0.054 Uiso 1 calc . . R
C3 C 0.2897(3) 0.4756(4) 0.2777(4) 0.0489(9) Uani 1 d . . .
H3 H 0.2601 0.5366 0.2120 0.059 Uiso 1 calc . . R
C4 C 0.2267(3) 0.3806(4) 0.2936(4) 0.0474(9) Uani 1 d . . .
H4 H 0.1550 0.3770 0.2391 0.057 Uiso 1 calc . . R
C5 C 0.2706(2) 0.2909(3) 0.3906(4) 0.0419(8) Uani 1 d . . .
C6 C 0.3773(2) 0.2969(3) 0.4755(3) 0.0379(8) Uani 1 d . . .
C7 C 0.4058(3) 0.2422(5) 0.7051(4) 0.0613(12) Uani 1 d . . .
H7A H 0.4428 0.3196 0.7370 0.074 Uiso 1 calc . . R
H7B H 0.3308 0.2543 0.6922 0.074 Uiso 1 calc . . R
C8 C 0.5586(3) 0.1571(7) 0.8559(5) 0.0938(18) Uani 1 d . . .
H8A H 0.5878 0.1223 0.7902 0.141 Uiso 1 calc . . GR
H8B H 0.5830 0.1105 0.9406 0.141 Uiso 1 calc . . GR
H8C H 0.5816 0.2414 0.8743 0.141 Uiso 1 calc . . GR
C9 C 0.2358(3) 0.0497(4) 0.3202(4) 0.0490(9) Uani 1 d . . .
C10 C 0.1798(3) 0.0344(4) 0.1801(4) 0.0555(10) Uani 1 d . . .
H10 H 0.1196 0.0819 0.1361 0.067 Uiso 1 calc . . R
C11 C 0.2154(3) -0.0533(4) 0.1072(4) 0.0624(11) Uani 1 d . . .
H11 H 0.1783 -0.0638 0.0130 0.075 Uiso 1 calc . . R
C12 C 0.3038(3) -0.1253(4) 0.1692(4) 0.0553(10) Uani 1 d . . .
C13 C 0.3574(3) -0.1111(4) 0.3107(4) 0.0581(10) Uani 1 d . . .
H13 H 0.4159 -0.1610 0.3553 0.070 Uiso 1 calc . . R
C14 C 0.3238(3) -0.0221(4) 0.3859(4) 0.0537(9) Uani 1 d . . .
H14 H 0.3607 -0.0114 0.4800 0.064 Uiso 1 calc . . R
C15 C 0.3428(4) -0.2184(5) 0.0866(5) 0.0798(14) Uani 1 d . . .
H15A H 0.4175 -0.2058 0.1034 0.120 Uiso 1 calc . . GR
H15B H 0.3039 -0.2079 -0.0105 0.120 Uiso 1 calc . . GR
H15C H 0.3315 -0.3006 0.1143 0.120 Uiso 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
S1 O1 1.491(3) . ?
S1 C5 1.810(4) . ?
S1 C9 1.798(4) . ?
O2 C6 1.384(4) . ?
O2 C7 1.432(4) . ?
O3 C7 1.355(5) . ?
O3 C8 1.405(5) . ?
C1 C1 1.496(6) 2_656 ?
C1 C2 1.397(5) . ?
C1 C6 1.390(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.369(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.370(5) . ?
C5 C6 1.394(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.386(6) . ?
C9 C14 1.377(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.374(6) . ?
C12 C13 1.391(6) . ?
C12 C15 1.515(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.397(6) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
O1 S1 C5 104.78(17) . . ?
O1 S1 C9 106.91(18) . . ?
C9 S1 C5 97.12(15) . . ?
C6 O2 C7 111.5(3) . . ?
C7 O3 C8 112.2(4) . . ?
C2 C1 C1 122.4(2) . 2_656 ?
C6 C1 C1 119.0(2) . 2_656 ?
C6 C1 C2 118.6(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.3(3) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 S1 120.8(3) . . ?
C4 C5 C6 121.0(3) . . ?
C6 C5 S1 118.2(3) . . ?
O2 C6 C1 120.8(3) . . ?
O2 C6 C5 119.3(3) . . ?
C1 C6 C5 119.8(3) . . ?
O2 C7 H7A 109.7 . . ?
O2 C7 H7B 109.7 . . ?
O3 C7 O2 109.9(3) . . ?
O3 C7 H7A 109.7 . . ?
O3 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
O3 C8 H8A 109.5 . . ?
O3 C8 H8B 109.5 . . ?
O3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 S1 118.8(3) . . ?
C14 C9 S1 120.5(3) . . ?
C14 C9 C10 120.7(4) . . ?
C9 C10 H10 120.8 . . ?
C9 C10 C11 118.5(4) . . ?
C11 C10 H10 120.8 . . ?
C10 C11 H11 118.9 . . ?
C12 C11 C10 122.2(4) . . ?
C12 C11 H11 118.9 . . ?
C11 C12 C13 118.6(4) . . ?
C11 C12 C15 121.2(4) . . ?
C13 C12 C15 120.2(4) . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.1(4) . . ?
C14 C13 H13 119.9 . . ?
C9 C14 C13 119.8(4) . . ?
C9 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C5 C6 O2 -0.9(4) . . . . ?
S1 C5 C6 C1 178.5(3) . . . . ?
S1 C9 C10 C11 179.7(3) . . . . ?
S1 C9 C14 C13 179.4(3) . . . . ?
O1 S1 C5 C4 -8.3(3) . . . . ?
O1 S1 C5 C6 170.0(3) . . . . ?
O1 S1 C9 C10 16.4(3) . . . . ?
O1 S1 C9 C14 -162.8(3) . . . . ?
C1 C1 C2 C3 177.5(3) 2_656 . . . ?
C1 C1 C6 O2 3.6(5) 2_656 . . . ?
C1 C1 C6 C5 -175.8(3) 2_656 . . . ?
C1 C2 C3 C4 -0.3(6) . . . . ?
C2 C1 C6 O2 -177.7(3) . . . . ?
C2 C1 C6 C5 3.0(5) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C3 C4 C5 S1 179.9(3) . . . . ?
C3 C4 C5 C6 1.7(5) . . . . ?
C4 C5 C6 O2 177.4(3) . . . . ?
C4 C5 C6 C1 -3.3(5) . . . . ?
C5 S1 C9 C10 -91.5(3) . . . . ?
C5 S1 C9 C14 89.4(3) . . . . ?
C6 O2 C7 O3 -179.7(3) . . . . ?
C6 C1 C2 C3 -1.2(5) . . . . ?
C7 O2 C6 C1 90.5(4) . . . . ?
C7 O2 C6 C5 -90.2(4) . . . . ?
C8 O3 C7 O2 77.8(5) . . . . ?
C9 S1 C5 C4 101.3(3) . . . . ?
C9 S1 C5 C6 -80.4(3) . . . . ?
C9 C10 C11 C12 0.3(6) . . . . ?
C10 C9 C14 C13 0.3(6) . . . . ?
C10 C11 C12 C13 1.5(6) . . . . ?
C10 C11 C12 C15 -178.5(4) . . . . ?
C11 C12 C13 C14 -2.3(6) . . . . ?
C12 C13 C14 C9 1.5(6) . . . . ?
C14 C9 C10 C11 -1.1(5) . . . . ?
C15 C12 C13 C14 177.7(4) . . . . ?

