# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_2017acc0012_k1_100k
_database_code_depnum_ccdc_archive 'CCDC 1538124'
_audit_update_record             
;
2017-03-15 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_audit_creation_date             2017-03-15
_audit_creation_method           
;
Olex2 1.2-alpha
(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         'C30 H29 N3 O5 S2'
_chemical_formula_sum            'C30 H29 N3 O5 S2'
_chemical_formula_weight         575.68
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C35 H35 N23 O3 S1'
_chemical_oxdiff_usercomment     'Caffeine Hydrate recollection'
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'
N N 0.0061 0.0033 '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'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.60010(10)
_cell_length_b                   17.1655(2)
_cell_length_c                   9.58080(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.4730(10)
_cell_angle_gamma                90
_cell_volume                     1410.06(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11186
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.4890
_cell_measurement_theta_min      4.0660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78189
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.9g (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             604
_exptl_crystal_recrystallization_method 
'The material was recrystallised from --- by slow evaporation'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17745
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.694
_diffrn_reflns_theta_min         3.879
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -100.00  15.00   1.00    4.00    --  -19.10 -57.00  60.00  115
  2  ω   -104.00  17.00   1.00    4.00    --  -19.10 -72.00 -60.00  121
  3  ω    -43.00  17.00   1.00    4.00    --  -19.10 -72.00 120.00   60
  4  ω    -42.00  -2.00   1.00    4.00    --  -19.10  38.00 -90.00   40
  5  ω      9.00  64.00   1.00    4.00    --  -19.10  38.00 -90.00   55
  6  ω    -54.00  61.00   1.00    4.00    --  -19.10  57.00  30.00  115
;
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-HF'
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0374620000
_diffrn_orient_matrix_UB_12      -0.0367879000
_diffrn_orient_matrix_UB_13      0.0053835000
_diffrn_orient_matrix_UB_21      -0.0734586000
_diffrn_orient_matrix_UB_22      -0.0185191000
_diffrn_orient_matrix_UB_23      0.0026351000
_diffrn_orient_matrix_UB_31      -0.0063782000
_diffrn_orient_matrix_UB_32      -0.0033583000
_diffrn_orient_matrix_UB_33      -0.0740350000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.936
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                7054
_reflns_number_total             7251
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.39.9g (Rigaku OD, 2015) 
;
_computing_data_collection       
;
CrysAlisPro 1.171.39.9g (Rigaku OD, 2015) 
;
_computing_data_reduction        
;
CrysAlisPro 1.171.39.9g (Rigaku OD, 2015) 
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 3183 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         7251
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0310
_refine_ls_restrained_S_all      1.042
_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)+(0.0308P)²+0.2549P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0704
_refine_special_details          ?
_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 Ternary CH refined with riding coordinates:
 C1(H1), C4(H4), C8(H8), C23(H23)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
2.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C)
;
_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
C1 C 1.0923(3) 0.28006(13) 0.3313(2) 0.0197(4) Uani 1 1 d . . . . .
H1 H 1.130623 0.334871 0.325369 0.024 Uiso 1 1 calc R . . . .
C2 C 1.1957(3) 0.22965(15) 0.2451(3) 0.0308(5) Uani 1 1 d . . . . .
H2A H 1.305009 0.236093 0.280202 0.046 Uiso 1 1 calc GR . . . .
H2B H 1.182660 0.245676 0.146666 0.046 Uiso 1 1 calc GR . . . .
H2C H 1.165635 0.174849 0.253019 0.046 Uiso 1 1 calc GR . . . .
C3 C 1.1092(3) 0.25685(15) 0.4856(2) 0.0255(5) Uani 1 1 d . . . . .
H3A H 1.075258 0.202751 0.495332 0.038 Uiso 1 1 calc GR . . . .
H3B H 1.044506 0.291095 0.538902 0.038 Uiso 1 1 calc GR . . . .
H3C H 1.218579 0.261799 0.521447 0.038 Uiso 1 1 calc GR . . . .
C4 C 0.9236(3) 0.27911(12) 0.2671(2) 0.0185(4) Uani 1 1 d . . . . .
H4 H 0.923929 0.292821 0.165725 0.022 Uiso 1 1 calc R . . . .
C5 C 0.8365(3) 0.20204(14) 0.2788(3) 0.0269(5) Uani 1 1 d . . . . .
H5A H 0.911692 0.158508 0.291963 0.032 Uiso 1 1 calc R . . . .
H5B H 0.768785 0.192372 0.192149 0.032 Uiso 1 1 calc R . . . .
C6 C 0.7347(2) 0.30866(13) 0.4367(2) 0.0176(4) Uani 1 1 d . . . . .
C7 C 0.6737(2) 0.35890(12) 0.5265(2) 0.0178(4) Uani 1 1 d . . . . .
C8 C 0.7081(2) 0.44474(12) 0.5217(2) 0.0150(4) Uani 1 1 d . . . . .
H8 H 0.617629 0.472512 0.558548 0.018 Uiso 1 1 calc R . . . .
C9 C 0.7109(2) 0.46688(11) 0.3645(2) 0.0131(4) Uani 1 1 d . . . . .
C10 C 0.8272(2) 0.41502(11) 0.2943(2) 0.0129(4) Uani 1 1 d . . . . .
C11 C 0.8533(2) 0.46689(11) 0.6157(2) 0.0159(4) Uani 1 1 d . . . . .
C12 C 1.0052(3) 0.45819(13) 0.5767(2) 0.0200(4) Uani 1 1 d . . . . .
H12 H 1.021715 0.438296 0.486536 0.024 Uiso 1 1 calc R . . . .
C13 C 1.1329(3) 0.47819(14) 0.6678(2) 0.0227(5) Uani 1 1 d . . . . .
H13 H 1.235694 0.472247 0.639440 0.027 Uiso 1 1 calc R . . . .
C14 C 1.1101(3) 0.50682(13) 0.8001(2) 0.0250(5) Uani 1 1 d . . . . .
H14 H 1.196821 0.520580 0.862746 0.030 Uiso 1 1 calc R . . . .
C15 C 0.9605(3) 0.51509(15) 0.8399(2) 0.0292(5) Uani 1 1 d . . . . .
H15 H 0.944423 0.534335 0.930588 0.035 Uiso 1 1 calc R . . . .
C16 C 0.8328(3) 0.49560(13) 0.7487(2) 0.0228(5) Uani 1 1 d . . . . .
H16 H 0.730417 0.501957 0.777643 0.027 Uiso 1 1 calc R . . . .
C17 C 0.5504(2) 0.45515(11) 0.2864(2) 0.0139(4) Uani 1 1 d . . . . .
C18 C 0.5342(2) 0.41986(12) 0.1553(2) 0.0182(4) Uani 1 1 d . . . . .
H18 H 0.623783 0.399795 0.115555 0.022 Uiso 1 1 calc R . . . .
C19 C 0.3886(3) 0.41352(13) 0.0814(2) 0.0222(4) Uani 1 1 d . . . . .
H19 H 0.379091 0.389544 -0.008233 0.027 Uiso 1 1 calc R . . . .
C20 C 0.2576(3) 0.44244(14) 0.1395(2) 0.0226(5) Uani 1 1 d . . . . .
H20 H 0.157809 0.438029 0.090188 0.027 Uiso 1 1 calc R . . . .
C21 C 0.2730(2) 0.47783(14) 0.2700(2) 0.0212(4) Uani 1 1 d . . . . .
H21 H 0.183142 0.497626 0.309666 0.025 Uiso 1 1 calc R . . . .
C22 C 0.4170(2) 0.48463(13) 0.3428(2) 0.0178(4) Uani 1 1 d . . . . .
H22 H 0.425770 0.509452 0.431659 0.021 Uiso 1 1 calc R . . . .
C23 C 0.7386(2) 0.60178(11) 0.1803(2) 0.0131(4) Uani 1 1 d . . . . .
H23 H 0.757248 0.556682 0.117657 0.016 Uiso 1 1 calc R . . . .
C24 C 0.5710(2) 0.62980(12) 0.1502(2) 0.0161(4) Uani 1 1 d . . . . .
H24A H 0.498289 0.587974 0.173763 0.019 Uiso 1 1 calc R . . . .
H24B H 0.552516 0.675468 0.209787 0.019 Uiso 1 1 calc R . . . .
C25 C 0.8614(2) 0.66380(12) 0.16100(19) 0.0137(4) Uani 1 1 d . . . . .
C26 C 1.0146(2) 0.63935(13) 0.1490(2) 0.0191(4) Uani 1 1 d . . . . .
H26 H 1.038022 0.585262 0.149971 0.023 Uiso 1 1 calc R . . . .
C27 C 1.1326(3) 0.69287(15) 0.1358(2) 0.0250(5) Uani 1 1 d . . . . .
H27 H 1.236556 0.675418 0.129069 0.030 Uiso 1 1 calc R . . . .
C28 C 1.0997(3) 0.77202(15) 0.1324(2) 0.0262(5) Uani 1 1 d . . . . .
H28 H 1.180530 0.808778 0.121778 0.031 Uiso 1 1 calc R . . . .
C29 C 0.9488(3) 0.79697(13) 0.1445(2) 0.0239(5) Uani 1 1 d . . . . .
H29 H 0.925803 0.851108 0.142810 0.029 Uiso 1 1 calc R . . . .
C30 C 0.8300(3) 0.74309(12) 0.1592(2) 0.0184(4) Uani 1 1 d . . . . .
H30 H 0.726628 0.760813 0.168085 0.022 Uiso 1 1 calc R . . . .
N1 N 0.8269(2) 0.33741(10) 0.33536(18) 0.0152(3) Uani 1 1 d . . . . .
N2 N 0.5758(2) 0.33097(12) 0.6277(2) 0.0232(4) Uani 1 1 d . . . . .
N3 N 0.5395(2) 0.65184(11) -0.00152(18) 0.0181(4) Uani 1 1 d . . . . .
O1 O 0.5493(2) 0.25962(11) 0.63082(19) 0.0309(4) Uani 1 1 d . . . . .
O2 O 0.5208(2) 0.37774(11) 0.70888(18) 0.0327(4) Uani 1 1 d . . . . .
O3 O 0.90814(16) 0.43689(9) 0.20415(15) 0.0157(3) Uani 1 1 d . . . . .
O4 O 0.5735(2) 0.60452(11) -0.08928(17) 0.0322(4) Uani 1 1 d . . . . .
O5 O 0.47740(19) 0.71463(10) -0.02882(17) 0.0289(4) Uani 1 1 d . . . . .
S1 S 0.71812(7) 0.20854(3) 0.42919(6) 0.02642(13) Uani 1 1 d . . . . .
S2 S 0.76981(6) 0.56978(3) 0.36394(5) 0.01419(10) Uani 1 1 d . . . . .


_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
C1 H1 1.0000 . ?
C1 C2 1.529(3) . ?
C1 C3 1.527(3) . ?
C1 C4 1.531(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4 1.0000 . ?
C4 C5 1.529(3) . ?
C4 N1 1.485(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 S1 1.831(3) . ?
C6 C7 1.353(3) . ?
C6 N1 1.391(3) . ?
C6 S1 1.726(2) . ?
C7 C8 1.504(3) . ?
C7 N2 1.417(3) . ?
C8 H8 1.0000 . ?
C8 C9 1.555(3) . ?
C8 C11 1.529(3) . ?
C9 C10 1.534(3) . ?
C9 C17 1.531(3) . ?
C9 S2 1.838(2) . ?
C10 N1 1.389(3) . ?
C10 O3 1.211(2) . ?
C11 C12 1.394(3) . ?
C11 C16 1.391(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.392(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.388(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.377(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.389(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.392(3) . ?
C17 C22 1.400(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.394(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.387(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.387(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.378(3) . ?
C22 H22 0.9500 . ?
C23 H23 1.0000 . ?
C23 C24 1.525(3) . ?
C23 C25 1.521(3) . ?
C23 S2 1.8429(19) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 N3 1.506(3) . ?
C25 C26 1.396(3) . ?
C25 C30 1.387(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.382(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.388(4) . ?
C28 H28 0.9500 . ?
C28 C29 1.380(4) . ?
C29 H29 0.9500 . ?
C29 C30 1.393(3) . ?
C30 H30 0.9500 . ?
N2 O1 1.246(3) . ?
N2 O2 1.237(3) . ?
N3 O4 1.221(3) . ?
N3 O5 1.222(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
C2 C1 H1 107.1 . . ?
C2 C1 C4 110.48(19) . . ?
C3 C1 H1 107.1 . . ?
C3 C1 C2 111.10(18) . . ?
C3 C1 C4 113.67(18) . . ?
C4 C1 H1 107.1 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4 108.3 . . ?
C5 C4 C1 115.75(18) . . ?
C5 C4 H4 108.3 . . ?
N1 C4 C1 111.21(16) . . ?
N1 C4 H4 108.3 . . ?
N1 C4 C5 104.87(18) . . ?
C4 C5 H5A 110.1 . . ?
C4 C5 H5B 110.1 . . ?
C4 C5 S1 108.08(15) . . ?
H5A C5 H5B 108.4 . . ?
S1 C5 H5A 110.1 . . ?
S1 C5 H5B 110.1 . . ?
C7 C6 N1 119.22(19) . . ?
C7 C6 S1 128.81(16) . . ?
N1 C6 S1 111.96(16) . . ?
C6 C7 C8 121.22(18) . . ?
C6 C7 N2 120.02(19) . . ?
N2 C7 C8 118.76(19) . . ?
C7 C8 H8 107.2 . . ?
C7 C8 C9 106.67(16) . . ?
C7 C8 C11 112.27(16) . . ?
C9 C8 H8 107.2 . . ?
C11 C8 H8 107.2 . . ?
C11 C8 C9 115.83(16) . . ?
C8 C9 S2 105.25(13) . . ?
C10 C9 C8 110.04(15) . . ?
C10 C9 S2 111.52(13) . . ?
C17 C9 C8 111.10(16) . . ?
C17 C9 C10 107.67(16) . . ?
C17 C9 S2 111.30(13) . . ?
N1 C10 C9 114.63(16) . . ?
O3 C10 C9 124.35(18) . . ?
O3 C10 N1 120.89(18) . . ?
C12 C11 C8 123.70(18) . . ?
C16 C11 C8 118.14(19) . . ?
C16 C11 C12 118.1(2) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.1(2) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 119.9(2) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.4(2) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.7(2) . . ?
C16 C15 H15 119.6 . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.7(2) . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C9 121.41(17) . . ?
C18 C17 C22 118.55(19) . . ?
C22 C17 C9 119.91(17) . . ?
C17 C18 H18 119.5 . . ?
C17 C18 C19 120.99(19) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.6(2) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 120.1 . . ?
C19 C20 C21 119.7(2) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.8(2) . . ?
C22 C21 H21 119.6 . . ?
C17 C22 H22 119.8 . . ?
C21 C22 C17 120.4(2) . . ?
C21 C22 H22 119.8 . . ?
C24 C23 H23 108.9 . . ?
C24 C23 S2 109.85(13) . . ?
C25 C23 H23 108.9 . . ?
C25 C23 C24 114.27(16) . . ?
C25 C23 S2 105.90(13) . . ?
S2 C23 H23 108.9 . . ?
C23 C24 H24A 109.4 . . ?
C23 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
N3 C24 C23 110.98(16) . . ?
N3 C24 H24A 109.4 . . ?
N3 C24 H24B 109.4 . . ?
C26 C25 C23 117.92(18) . . ?
C30 C25 C23 123.53(19) . . ?
C30 C25 C26 118.52(19) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 C25 120.8(2) . . ?
C27 C26 H26 119.6 . . ?
C26 C27 H27 119.9 . . ?
C26 C27 C28 120.2(2) . . ?
C28 C27 H27 119.9 . . ?
C27 C28 H28 120.2 . . ?
C29 C28 C27 119.5(2) . . ?
C29 C28 H28 120.2 . . ?
C28 C29 H29 119.9 . . ?
C28 C29 C30 120.3(2) . . ?
C30 C29 H29 119.9 . . ?
C25 C30 C29 120.6(2) . . ?
C25 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C6 N1 C4 115.94(17) . . ?
C10 N1 C4 120.54(16) . . ?
C10 N1 C6 123.47(17) . . ?
O1 N2 C7 117.93(19) . . ?
O2 N2 C7 119.18(19) . . ?
O2 N2 O1 122.89(19) . . ?
O4 N3 C24 117.57(18) . . ?
O4 N3 O5 124.30(18) . . ?
O5 N3 C24 118.09(17) . . ?
C6 S1 C5 92.54(11) . . ?
C9 S2 C23 105.66(9) . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder silicon oil'
_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 1.646
_oxdiff_exptl_absorpt_empirical_full_min 0.685
####################################################################### 
# 
# 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_2014acc0005
_database_code_depnum_ccdc_archive 'CCDC 1830928'
_audit_update_record             
;
2018-03-19 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_audit_creation_date             2014-10-22
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.10.16 svn.r3037 for OlexSys, GUI svn.r4914)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H17 N O5 S2'
_chemical_formula_sum            'C17 H17 N O5 S2'
_chemical_formula_weight         379.43
_chemical_absolute_configuration ad
_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 0.0033 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'
N N 0.0061 0.0033 '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'

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

_cell_length_a                   5.84070(10)
_cell_length_b                   14.9477(4)
_cell_length_c                   19.3104(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1685.90(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13829
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.5
_cell_measurement_theta_min      1.4
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.345
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21760
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.695
_diffrn_reflns_theta_min         2.923
_diffrn_ambient_temperature      120
_diffrn_detector                 'Image Plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'Rigaku IP'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
scan:
	Number of images: 36
	           Slice: 20.0000 - 200.0000
	     Image width: 5.0000
	        Exp time: 780.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 270.0000
	             XTD: 127.4000
	          2theta: -0.0449
scan:
	Number of images: 27
	           Slice: 53.0000 - 188.0000
	     Image width: 5.0000
	        Exp time: 780.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: -0.0449
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku R-AXIS Spider'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Mitegen
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.166520
_diffrn_orient_matrix_UB_12      0.009944
_diffrn_orient_matrix_UB_13      0.038548
_diffrn_orient_matrix_UB_21      -0.004212
_diffrn_orient_matrix_UB_22      -0.057958
_diffrn_orient_matrix_UB_23      0.033147
_diffrn_orient_matrix_UB_31      0.011591
_diffrn_orient_matrix_UB_32      -0.025689
_diffrn_orient_matrix_UB_33      -0.043445
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4287
_reflns_number_total             4321
_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       
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_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    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 1806 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.030(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         4321
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0228
_refine_ls_R_factor_gt           0.0226
_refine_ls_restrained_S_all      1.108
_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)+(0.0322P)²+0.1987P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0601
_refine_ls_wR_factor_ref         0.0602
_refine_special_details          ?
_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 Ternary CH refined with riding coordinates:
 C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C13(H13), C16(H16), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C9(H9A,H9B,H9C)
;
_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
S2 S 0.91339(6) 0.40201(2) 0.42220(2) 0.01442(8) Uani 1 1 d . . . . .
S1 S 0.73459(7) 0.24956(2) 0.32518(2) 0.01758(9) Uani 1 1 d . . . . .
O5 O 0.63727(19) 0.66350(7) 0.31933(6) 0.0176(2) Uani 1 1 d . . . . .
O2 O 0.8000(2) 0.51073(7) 0.21576(6) 0.0211(2) Uani 1 1 d . . . . .
O3 O 0.36351(19) 0.42022(7) 0.50769(5) 0.0177(2) Uani 1 1 d . . . . .
O4 O 0.9727(2) 0.59947(8) 0.34862(6) 0.0227(2) Uani 1 1 d . . . . .
O1 O 1.0107(2) 0.39805(8) 0.25931(6) 0.0246(3) Uani 1 1 d . . . . .
N1 N 0.4895(2) 0.35032(8) 0.40822(6) 0.0151(2) Uani 1 1 d . . . . .
C17 C 0.9116(3) 0.55383(10) 0.53338(8) 0.0199(3) Uani 1 1 d . . . . .
H17 H 1.0208 0.5089 0.5289 0.024 Uiso 1 1 calc R . . . .
C1 C 0.6916(2) 0.35783(9) 0.36356(7) 0.0138(3) Uani 1 1 d . . . . .
C6 C 0.6176(3) 0.51785(9) 0.36310(7) 0.0135(2) Uani 1 1 d . . . . .
H6 H 0.4567 0.5365 0.3625 0.016 Uiso 1 1 calc R . . . .
C10 C 0.7668(3) 0.59693(9) 0.34379(7) 0.0148(3) Uani 1 1 d . . . . .
C8 C 0.8430(3) 0.44493(10) 0.26098(8) 0.0179(3) Uani 1 1 d . . . . .
C12 C 0.7190(3) 0.55387(9) 0.49083(7) 0.0143(3) Uani 1 1 d . . . . .
C4 C 0.4881(2) 0.41527(9) 0.45775(7) 0.0136(3) Uani 1 1 d . . . . .
C13 C 0.5575(3) 0.62226(10) 0.49761(8) 0.0176(3) Uani 1 1 d . . . . .
H13 H 0.4285 0.6227 0.4694 0.021 Uiso 1 1 calc R . . . .
C11 C 0.7638(3) 0.73965(9) 0.29318(8) 0.0206(3) Uani 1 1 d . . . . .
H11A H 0.8564 0.7213 0.2546 0.031 Uiso 1 1 calc GR . . . .
H11B H 0.8604 0.7630 0.3291 0.031 Uiso 1 1 calc GR . . . .
H11C H 0.6585 0.7851 0.2784 0.031 Uiso 1 1 calc GR . . . .
C3 C 0.3667(3) 0.26552(9) 0.40733(8) 0.0180(3) Uani 1 1 d . . . . .
H3A H 0.2429 0.2672 0.3739 0.022 Uiso 1 1 calc R . . . .
H3B H 0.3033 0.2525 0.4526 0.022 Uiso 1 1 calc R . . . .
C5 C 0.6797(2) 0.48200(9) 0.43757(7) 0.0125(2) Uani 1 1 d . . . . .
C7 C 0.6492(3) 0.43594(9) 0.31325(7) 0.0146(3) Uani 1 1 d . . . . .
H7 H 0.5056 0.4254 0.2883 0.018 Uiso 1 1 calc R . . . .
C16 C 0.9411(3) 0.62124(11) 0.58281(9) 0.0241(3) Uani 1 1 d . . . . .
H16 H 1.0692 0.6207 0.6114 0.029 Uiso 1 1 calc R . . . .
C14 C 0.5888(3) 0.68966(10) 0.54639(8) 0.0207(3) Uani 1 1 d . . . . .
H14 H 0.4815 0.7354 0.5502 0.025 Uiso 1 1 calc R . . . .
C15 C 0.7793(3) 0.68909(10) 0.58944(8) 0.0224(3) Uani 1 1 d . . . . .
H15 H 0.7987 0.7337 0.6225 0.027 Uiso 1 1 calc R . . . .
C2 C 0.5437(3) 0.19522(10) 0.38706(9) 0.0207(3) Uani 1 1 d . . . . .
H2A H 0.4698 0.1438 0.3661 0.025 Uiso 1 1 calc R . . . .
H2B H 0.6285 0.1753 0.4274 0.025 Uiso 1 1 calc R . . . .
C9 C 0.9793(3) 0.52607(12) 0.16528(8) 0.0260(4) Uani 1 1 d . . . . .
H9A H 0.9958 0.4741 0.1365 0.039 Uiso 1 1 calc GR . . . .
H9B H 1.1211 0.5376 0.1888 0.039 Uiso 1 1 calc GR . . . .
H9C H 0.9400 0.5767 0.1371 0.039 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
S2 C1 1.8432(15) . ?
S2 C5 1.8388(14) . ?
S1 C1 1.7976(14) . ?
S1 C2 1.8249(17) . ?
O5 C10 1.3363(18) . ?
O5 C11 1.4482(17) . ?
O2 C8 1.3390(18) . ?
O2 C9 1.449(2) . ?
O3 C4 1.2104(18) . ?
O4 C10 1.207(2) . ?
O1 C8 1.205(2) . ?
N1 C1 1.4662(18) . ?
N1 C4 1.3629(18) . ?
N1 C3 1.4563(18) . ?
C17 H17 0.9300 . ?
C17 C12 1.393(2) . ?
C17 C16 1.399(2) . ?
C1 C7 1.5390(19) . ?
C6 H6 0.9800 . ?
C6 C10 1.515(2) . ?
C6 C5 1.5769(19) . ?
C6 C7 1.5685(19) . ?
C8 C7 1.522(2) . ?
C12 C13 1.397(2) . ?
C12 C5 1.5050(18) . ?
C4 C5 1.549(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.391(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C2 1.525(2) . ?
C7 H7 0.9800 . ?
C16 H16 0.9300 . ?
C16 C15 1.392(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.389(2) . ?
C15 H15 0.9300 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
C5 S2 C1 79.06(6) . . ?
C1 S1 C2 92.60(7) . . ?
C10 O5 C11 114.81(12) . . ?
C8 O2 C9 114.77(13) . . ?
C4 N1 C1 111.29(11) . . ?
C4 N1 C3 128.71(13) . . ?
C3 N1 C1 117.13(11) . . ?
C12 C17 H17 120.0 . . ?
C12 C17 C16 120.10(15) . . ?
C16 C17 H17 120.0 . . ?
S1 C1 S2 118.53(8) . . ?
N1 C1 S2 103.41(9) . . ?
N1 C1 S1 106.63(9) . . ?
N1 C1 C7 107.47(11) . . ?
C7 C1 S2 103.23(9) . . ?
C7 C1 S1 116.44(10) . . ?
C10 C6 H6 109.1 . . ?
C10 C6 C5 110.94(11) . . ?
C10 C6 C7 112.96(11) . . ?
C5 C6 H6 109.1 . . ?
C7 C6 H6 109.1 . . ?
C7 C6 C5 105.51(11) . . ?
O5 C10 C6 110.00(13) . . ?
O4 C10 O5 124.63(14) . . ?
O4 C10 C6 125.36(14) . . ?
O2 C8 C7 110.94(13) . . ?
O1 C8 O2 124.23(14) . . ?
O1 C8 C7 124.81(14) . . ?
C17 C12 C13 119.37(13) . . ?
C17 C12 C5 121.75(13) . . ?
C13 C12 C5 118.89(13) . . ?
O3 C4 N1 127.32(13) . . ?
O3 C4 C5 126.54(13) . . ?
N1 C4 C5 106.14(11) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.30(15) . . ?
C14 C13 H13 119.8 . . ?
O5 C11 H11A 109.5 . . ?
O5 C11 H11B 109.5 . . ?
O5 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C3 H3A 110.6 . . ?
N1 C3 H3B 110.6 . . ?
N1 C3 C2 105.61(12) . . ?
H3A C3 H3B 108.8 . . ?
C2 C3 H3A 110.6 . . ?
C2 C3 H3B 110.6 . . ?
C6 C5 S2 104.15(9) . . ?
C12 C5 S2 117.45(10) . . ?
C12 C5 C6 114.57(11) . . ?
C12 C5 C4 113.47(12) . . ?
C4 C5 S2 99.11(9) . . ?
C4 C5 C6 106.39(11) . . ?
C1 C7 C6 102.93(11) . . ?
C1 C7 H7 109.0 . . ?
C6 C7 H7 109.0 . . ?
C8 C7 C1 111.47(12) . . ?
C8 C7 C6 115.20(12) . . ?
C8 C7 H7 109.0 . . ?
C17 C16 H16 119.9 . . ?
C15 C16 C17 120.28(15) . . ?
C15 C16 H16 119.9 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.39(15) . . ?
C15 C14 H14 119.8 . . ?
C16 C15 H15 120.2 . . ?
C14 C15 C16 119.55(14) . . ?
C14 C15 H15 120.2 . . ?
S1 C2 H2A 110.5 . . ?
S1 C2 H2B 110.5 . . ?
C3 C2 S1 105.99(10) . . ?
C3 C2 H2A 110.5 . . ?
C3 C2 H2B 110.5 . . ?
H2A C2 H2B 108.7 . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2014acc0007
_database_code_depnum_ccdc_archive 'CCDC 1830930'
_audit_update_record             
;
2018-03-19 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_audit_creation_date             2014-11-13
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.11.07 svn.r3078 for OlexSys, GUI svn.r4941)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H22 N2 O3 S2'
_chemical_formula_sum            'C24 H22 N2 O3 S2'
_chemical_formula_weight         450.55
_chemical_absolute_configuration ad
_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 0.0033 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'
N N 0.0061 0.0033 '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'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   14.3941(2)
_cell_length_b                   6.92520(11)
_cell_length_c                   21.6163(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.3263(15)
_cell_angle_gamma                90
_cell_volume                     2148.62(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    24195
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.9040
_cell_measurement_theta_min      2.4270
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            26689
_diffrn_reflns_point_group_measured_fraction_full 0.779
_diffrn_reflns_point_group_measured_fraction_max 0.654
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.054
_diffrn_reflns_theta_min         2.276
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -112.00   68.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000    0.0000    0.0000 180

#__ type_ start__ end____ width___ exp.time_
  2 omega  -45.00   57.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000   72.0000  -90.0000 102

#__ type_ start__ end____ width___ exp.time_
  3 omega  -84.00  -21.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000  -54.0000  120.0000 63

#__ type_ start__ end____ width___ exp.time_
  4 omega -112.00   -1.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000    0.0000   30.0000 111
;
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-HF'
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_UB_11      0.0269260000
_diffrn_orient_matrix_UB_12      0.0011782000
_diffrn_orient_matrix_UB_13      -0.0261620000
_diffrn_orient_matrix_UB_21      -0.0285449000
_diffrn_orient_matrix_UB_22      0.0747530000
_diffrn_orient_matrix_UB_23      -0.0134024000
_diffrn_orient_matrix_UB_31      0.0300804000
_diffrn_orient_matrix_UB_32      0.0699844000
_diffrn_orient_matrix_UB_33      0.0147656000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.331
_reflns_Friedel_fraction_full    0.516
_reflns_Friedel_fraction_max     0.351
_reflns_number_gt                9566
_reflns_number_total             9824
_reflns_odcompleteness_completeness 91.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.98
_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, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_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    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 2347 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     563
_refine_ls_number_reflns         9824
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0253
_refine_ls_restrained_S_all      1.038
_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)+(0.0402P)²+0.3568P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0651
_refine_ls_wR_factor_ref         0.0657
_refine_special_details          ?
_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 Ternary CH refined with riding coordinates:
 C101(H101), C104(H104), C107(H107), C108(H108), C201(H201), C204(H204),
 C207(H207), C208(H208)
2.b Secondary CH2 refined with riding coordinates:
 C105(H10G,H10H), C205(H20G,H20H)
2.c Aromatic/amide H refined with riding coordinates:
 C114(H114), C115(H115), C116(H116), C117(H117), C118(H118), C120(H120),
 C121(H121), C122(H122), C123(H123), C124(H124), C214(H214), C215(H215),
 C216(H216), C217(H217), C218(H218), C220(H220), C221(H221), C222(H222),
 C223(H223), C224(H224)
2.d Idealised Me refined as rotating group:
 C102(H10A,H10B,H10C), C103(H10D,H10E,H10F), C202(H20A,H20B,H20C), C203(H20D,
 H20E,H20F)
;
_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
S101 S 0.64418(3) -0.08687(6) 1.07761(2) 0.02068(8) Uani 1 1 d . . . . .
S102 S 0.78444(2) 0.09648(5) 0.99102(2) 0.01594(7) Uani 1 1 d . . . . .
O101 O 0.83926(8) 0.48948(18) 1.10436(5) 0.0208(2) Uani 1 1 d . . . . .
O102 O 0.54011(8) 0.0001(2) 0.94237(6) 0.0260(3) Uani 1 1 d . . . . .
O103 O 0.68302(8) 0.54251(18) 0.87474(5) 0.0212(2) Uani 1 1 d . . . . .
N101 N 0.73097(9) 0.2453(2) 1.09286(6) 0.0179(2) Uani 1 1 d . . . . .
N102 N 0.60845(8) 0.2552(2) 0.89394(6) 0.0166(2) Uani 1 1 d . . . . .
C101 C 0.63889(10) 0.2655(2) 1.18538(6) 0.0169(3) Uani 1 1 d . . . . .
H101 H 0.5819 0.2186 1.1625 0.020 Uiso 1 1 calc R . . . .
C102 C 0.63613(12) 0.2066(3) 1.25336(7) 0.0230(3) Uani 1 1 d . . . . .
H10A H 0.6880 0.2634 1.2773 0.035 Uiso 1 1 calc GR . . . .
H10B H 0.6396 0.0685 1.2567 0.035 Uiso 1 1 calc GR . . . .
H10C H 0.5791 0.2510 1.2688 0.035 Uiso 1 1 calc GR . . . .
C103 C 0.64135(11) 0.4855(2) 1.17996(7) 0.0203(3) Uani 1 1 d . . . . .
H10D H 0.5922 0.5403 1.2019 0.030 Uiso 1 1 calc GR . . . .
H10E H 0.6331 0.5219 1.1370 0.030 Uiso 1 1 calc GR . . . .
H10F H 0.7003 0.5326 1.1975 0.030 Uiso 1 1 calc GR . . . .
C104 C 0.72306(11) 0.1758(2) 1.15633(7) 0.0173(3) Uani 1 1 d . . . . .
H104 H 0.7800 0.2097 1.1817 0.021 Uiso 1 1 calc R . . . .
C105 C 0.71870(12) -0.0442(2) 1.14866(7) 0.0215(3) Uani 1 1 d . . . . .
H10G H 0.6923 -0.1037 1.1840 0.026 Uiso 1 1 calc R . . . .
H10H H 0.7805 -0.0968 1.1449 0.026 Uiso 1 1 calc R . . . .
C106 C 0.68893(10) 0.1257(2) 1.04250(6) 0.0157(3) Uani 1 1 d . . . . .
C107 C 0.61963(9) 0.2543(2) 1.00338(6) 0.0156(3) Uani 1 1 d . . . . .
H107 H 0.5692 0.3015 1.0274 0.019 Uiso 1 1 calc R . . . .
C108 C 0.67974(9) 0.4205(2) 0.98056(6) 0.0150(2) Uani 1 1 d . . . . .
H108 H 0.6637 0.5441 0.9991 0.018 Uiso 1 1 calc R . . . .
C109 C 0.78430(9) 0.3615(2) 0.99994(7) 0.0147(2) Uani 1 1 d . . . . .
C110 C 0.79149(10) 0.3785(2) 1.07229(7) 0.0164(3) Uani 1 1 d . . . . .
C111 C 0.58302(10) 0.1499(2) 0.94497(7) 0.0182(3) Uani 1 1 d . . . . .
C112 C 0.65954(9) 0.4224(2) 0.91050(7) 0.0160(2) Uani 1 1 d . . . . .
C113 C 0.59161(10) 0.1882(2) 0.83126(7) 0.0174(3) Uani 1 1 d . . . . .
C114 C 0.61918(10) 0.0020(3) 0.81702(7) 0.0204(3) Uani 1 1 d . . . . .
H114 H 0.6484 -0.0768 0.8474 0.024 Uiso 1 1 calc R . . . .
C115 C 0.60212(11) -0.0640(3) 0.75635(7) 0.0230(3) Uani 1 1 d . . . . .
H115 H 0.6194 -0.1887 0.7461 0.028 Uiso 1 1 calc R . . . .
C116 C 0.55926(11) 0.0558(3) 0.71109(7) 0.0238(3) Uani 1 1 d . . . . .
H116 H 0.5485 0.0113 0.6706 0.029 Uiso 1 1 calc R . . . .
C117 C 0.53254(11) 0.2407(3) 0.72599(7) 0.0226(3) Uani 1 1 d . . . . .
H117 H 0.5038 0.3198 0.6955 0.027 Uiso 1 1 calc R . . . .
C118 C 0.54849(10) 0.3095(2) 0.78662(7) 0.0196(3) Uani 1 1 d . . . . .
H118 H 0.5306 0.4338 0.7969 0.023 Uiso 1 1 calc R . . . .
C119 C 0.85770(9) 0.4632(2) 0.96623(7) 0.0165(3) Uani 1 1 d . . . . .
C120 C 0.89995(11) 0.3717(3) 0.91820(7) 0.0222(3) Uani 1 1 d . . . . .
H120 H 0.8843 0.2448 0.9080 0.027 Uiso 1 1 calc R . . . .
C121 C 0.96534(11) 0.4686(3) 0.88535(8) 0.0267(4) Uani 1 1 d . . . . .
H121 H 0.9936 0.4059 0.8537 0.032 Uiso 1 1 calc R . . . .
C122 C 0.98835(11) 0.6586(3) 0.89991(8) 0.0248(3) Uani 1 1 d . . . . .
H122 H 1.0315 0.7240 0.8778 0.030 Uiso 1 1 calc R . . . .
C123 C 0.94659(10) 0.7506(3) 0.94772(8) 0.0230(3) Uani 1 1 d . . . . .
H123 H 0.9621 0.8778 0.9576 0.028 Uiso 1 1 calc R . . . .
C124 C 0.88182(10) 0.6539(2) 0.98088(8) 0.0201(3) Uani 1 1 d . . . . .
H124 H 0.8544 0.7165 1.0129 0.024 Uiso 1 1 calc R . . . .
S201 S 0.92334(3) 0.27325(6) 0.40397(2) 0.02014(8) Uani 1 1 d . . . . .
S202 S 0.72760(2) 0.43591(5) 0.43185(2) 0.01569(7) Uani 1 1 d . . . . .
O201 O 0.73952(8) 0.80297(18) 0.30946(5) 0.0209(2) Uani 1 1 d . . . . .
O202 O 0.93523(7) 0.3922(2) 0.54687(5) 0.0236(2) Uani 1 1 d . . . . .
O203 O 0.72050(8) 0.8770(2) 0.55536(5) 0.0249(2) Uani 1 1 d . . . . .
N201 N 0.84294(8) 0.5856(2) 0.35695(6) 0.0170(2) Uani 1 1 d . . . . .
N202 N 0.82563(8) 0.6245(2) 0.56552(6) 0.0172(2) Uani 1 1 d . . . . .
C201 C 0.98022(10) 0.6067(2) 0.29277(7) 0.0172(3) Uani 1 1 d . . . . .
H201 H 1.0266 0.5742 0.3267 0.021 Uiso 1 1 calc R . . . .
C202 C 1.01563(11) 0.5352(3) 0.23167(8) 0.0235(3) Uani 1 1 d . . . . .
H20A H 0.9693 0.5598 0.1983 0.035 Uiso 1 1 calc GR . . . .
H20B H 1.0277 0.3990 0.2345 0.035 Uiso 1 1 calc GR . . . .
H20C H 1.0721 0.6020 0.2240 0.035 Uiso 1 1 calc GR . . . .
C203 C 0.96750(11) 0.8256(2) 0.29119(8) 0.0205(3) Uani 1 1 d . . . . .
H20D H 1.0252 0.8860 0.2827 0.031 Uiso 1 1 calc GR . . . .
H20E H 0.9491 0.8692 0.3306 0.031 Uiso 1 1 calc GR . . . .
H20F H 0.9202 0.8591 0.2593 0.031 Uiso 1 1 calc GR . . . .
C204 C 0.88850(10) 0.5042(2) 0.30425(7) 0.0170(3) Uani 1 1 d . . . . .
H204 H 0.8459 0.5168 0.2669 0.020 Uiso 1 1 calc R . . . .
C205 C 0.89960(11) 0.2891(2) 0.31998(7) 0.0201(3) Uani 1 1 d . . . . .
H20G H 0.9507 0.2340 0.2991 0.024 Uiso 1 1 calc R . . . .
H20H H 0.8430 0.2193 0.3070 0.024 Uiso 1 1 calc R . . . .
C206 C 0.85103(9) 0.4787(2) 0.41531(7) 0.0157(3) Uani 1 1 d . . . . .
C207 C 0.88404(9) 0.6226(2) 0.46650(7) 0.0159(3) Uani 1 1 d . . . . .
H207 H 0.9438 0.6816 0.4584 0.019 Uiso 1 1 calc R . . . .
C208 C 0.80542(9) 0.7746(2) 0.46686(7) 0.0151(2) Uani 1 1 d . . . . .
H208 H 0.8274 0.9026 0.4553 0.018 Uiso 1 1 calc R . . . .
C209 C 0.72573(9) 0.6990(2) 0.41861(7) 0.0143(2) Uani 1 1 d . . . . .
C210 C 0.76762(9) 0.7068(2) 0.35394(7) 0.0159(3) Uani 1 1 d . . . . .
C211 C 0.88758(9) 0.5290(2) 0.52995(7) 0.0173(3) Uani 1 1 d . . . . .
C212 C 0.77605(9) 0.7728(2) 0.53306(7) 0.0175(3) Uani 1 1 d . . . . .
C213 C 0.80947(9) 0.5641(3) 0.62756(7) 0.0194(3) Uani 1 1 d . . . . .
C214 C 0.78448(10) 0.3728(3) 0.63702(8) 0.0240(3) Uani 1 1 d . . . . .
H214 H 0.7774 0.2870 0.6039 0.029 Uiso 1 1 calc R . . . .
C215 C 0.77027(11) 0.3125(3) 0.69695(9) 0.0309(4) Uani 1 1 d . . . . .
H215 H 0.7538 0.1850 0.7041 0.037 Uiso 1 1 calc R . . . .
C216 C 0.78052(11) 0.4415(4) 0.74607(8) 0.0335(4) Uani 1 1 d . . . . .
H216 H 0.7711 0.4001 0.7860 0.040 Uiso 1 1 calc R . . . .
C217 C 0.80464(12) 0.6315(4) 0.73583(8) 0.0316(4) Uani 1 1 d . . . . .
H217 H 0.8108 0.7175 0.7689 0.038 Uiso 1 1 calc R . . . .
C218 C 0.81983(11) 0.6950(3) 0.67622(8) 0.0248(3) Uani 1 1 d . . . . .
H218 H 0.8365 0.8225 0.6692 0.030 Uiso 1 1 calc R . . . .
C219 C 0.63235(9) 0.7955(2) 0.42009(6) 0.0154(3) Uani 1 1 d . . . . .
C220 C 0.55417(10) 0.6967(3) 0.43763(7) 0.0175(3) Uani 1 1 d . . . . .
H220 H 0.5591 0.5673 0.4489 0.021 Uiso 1 1 calc R . . . .
C221 C 0.46825(10) 0.7910(3) 0.43840(7) 0.0216(3) Uani 1 1 d . . . . .
H221 H 0.4163 0.7241 0.4500 0.026 Uiso 1 1 calc R . . . .
C222 C 0.46055(10) 0.9837(3) 0.42184(7) 0.0221(3) Uani 1 1 d . . . . .
H222 H 0.4034 1.0462 0.4221 0.027 Uiso 1 1 calc R . . . .
C223 C 0.53864(10) 1.0840(3) 0.40478(7) 0.0201(3) Uani 1 1 d . . . . .
H223 H 0.5336 1.2138 0.3940 0.024 Uiso 1 1 calc R . . . .
C224 C 0.62404(10) 0.9904(2) 0.40377(7) 0.0170(3) Uani 1 1 d . . . . .
H224 H 0.6758 1.0578 0.3922 0.020 Uiso 1 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
S101 C105 1.8297(16) . ?
S101 C106 1.7977(16) . ?
S102 C106 1.8439(15) . ?
S102 C109 1.8455(16) . ?
O101 C110 1.2135(19) . ?
O102 C111 1.207(2) . ?
O103 C112 1.2012(19) . ?
N101 C104 1.4665(19) . ?
N101 C106 1.4620(19) . ?
N101 C110 1.366(2) . ?
N102 C111 1.3939(19) . ?
N102 C112 1.403(2) . ?
N102 C113 1.4355(19) . ?
C101 H101 0.9800 . ?
C101 C102 1.528(2) . ?
C101 C103 1.529(2) . ?
C101 C104 1.537(2) . ?
C102 H10A 0.9600 . ?
C102 H10B 0.9600 . ?
C102 H10C 0.9600 . ?
C103 H10D 0.9600 . ?
C103 H10E 0.9600 . ?
C103 H10F 0.9600 . ?
C104 H104 0.9800 . ?
C104 C105 1.533(2) . ?
C105 H10G 0.9700 . ?
C105 H10H 0.9700 . ?
C106 C107 1.541(2) . ?
C107 H107 0.9800 . ?
C107 C108 1.543(2) . ?
C107 C111 1.515(2) . ?
C108 H108 0.9800 . ?
C108 C109 1.5850(19) . ?
C108 C112 1.5206(19) . ?
C109 C110 1.564(2) . ?
C109 C119 1.503(2) . ?
C113 C114 1.390(2) . ?
C113 C118 1.390(2) . ?
C114 H114 0.9300 . ?
C114 C115 1.393(2) . ?
C115 H115 0.9300 . ?
C115 C116 1.391(2) . ?
C116 H116 0.9300 . ?
C116 C117 1.382(3) . ?
C117 H117 0.9300 . ?
C117 C118 1.397(2) . ?
C118 H118 0.9300 . ?
C119 C120 1.394(2) . ?
C119 C124 1.396(2) . ?
C120 H120 0.9300 . ?
C120 C121 1.393(2) . ?
C121 H121 0.9300 . ?
C121 C122 1.387(3) . ?
C122 H122 0.9300 . ?
C122 C123 1.389(2) . ?
C123 H123 0.9300 . ?
C123 C124 1.390(2) . ?
C124 H124 0.9300 . ?
S201 C205 1.8252(16) . ?
S201 C206 1.7907(15) . ?
S202 C206 1.8622(14) . ?
S202 C209 1.8444(16) . ?
O201 C210 1.2138(18) . ?
O202 C211 1.2100(19) . ?
O203 C212 1.2043(19) . ?
N201 C204 1.4690(19) . ?
N201 C206 1.4595(19) . ?
N201 C210 1.3688(18) . ?
N202 C211 1.3881(19) . ?
N202 C212 1.408(2) . ?
N202 C213 1.4404(19) . ?
C201 H201 0.9800 . ?
C201 C202 1.533(2) . ?
C201 C203 1.527(2) . ?
C201 C204 1.535(2) . ?
C202 H20A 0.9600 . ?
C202 H20B 0.9600 . ?
C202 H20C 0.9600 . ?
C203 H20D 0.9600 . ?
C203 H20E 0.9600 . ?
C203 H20F 0.9600 . ?
C204 H204 0.9800 . ?
C204 C205 1.534(2) . ?
C205 H20G 0.9700 . ?
C205 H20H 0.9700 . ?
C206 C207 1.537(2) . ?
C207 H207 0.9800 . ?
C207 C208 1.546(2) . ?
C207 C211 1.514(2) . ?
C208 H208 0.9800 . ?
C208 C209 1.5801(19) . ?
C208 C212 1.522(2) . ?
C209 C210 1.565(2) . ?
C209 C219 1.5034(19) . ?
C213 C214 1.392(3) . ?
C213 C218 1.389(2) . ?
C214 H214 0.9300 . ?
C214 C215 1.391(2) . ?
C215 H215 0.9300 . ?
C215 C216 1.387(3) . ?
C216 H216 0.9300 . ?
C216 C217 1.383(3) . ?
C217 H217 0.9300 . ?
C217 C218 1.394(2) . ?
C218 H218 0.9300 . ?
C219 C220 1.394(2) . ?
C219 C224 1.398(2) . ?
C220 H220 0.9300 . ?
C220 C221 1.400(2) . ?
C221 H221 0.9300 . ?
C221 C222 1.384(3) . ?
C222 H222 0.9300 . ?
C222 C223 1.394(2) . ?
C223 H223 0.9300 . ?
C223 C224 1.391(2) . ?
C224 H224 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
C106 S101 C105 90.92(7) . . ?
C106 S102 C109 79.69(7) . . ?
C106 N101 C104 116.98(12) . . ?
C110 N101 C104 128.51(13) . . ?
C110 N101 C106 112.24(12) . . ?
C111 N102 C112 113.18(12) . . ?
C111 N102 C113 122.82(14) . . ?
C112 N102 C113 123.74(13) . . ?
C102 C101 H101 108.4 . . ?
C102 C101 C103 110.00(13) . . ?
C102 C101 C104 111.30(12) . . ?
C103 C101 H101 108.4 . . ?
C103 C101 C104 110.38(13) . . ?
C104 C101 H101 108.4 . . ?
C101 C102 H10A 109.5 . . ?
C101 C102 H10B 109.5 . . ?
C101 C102 H10C 109.5 . . ?
H10A C102 H10B 109.5 . . ?
H10A C102 H10C 109.5 . . ?
H10B C102 H10C 109.5 . . ?
C101 C103 H10D 109.5 . . ?
C101 C103 H10E 109.5 . . ?
C101 C103 H10F 109.5 . . ?
H10D C103 H10E 109.5 . . ?
H10D C103 H10F 109.5 . . ?
H10E C103 H10F 109.5 . . ?
N101 C104 C101 111.63(12) . . ?
N101 C104 H104 109.0 . . ?
N101 C104 C105 103.32(12) . . ?
C101 C104 H104 109.0 . . ?
C105 C104 C101 114.77(14) . . ?
C105 C104 H104 109.0 . . ?
S101 C105 H10G 110.6 . . ?
S101 C105 H10H 110.6 . . ?
C104 C105 S101 105.55(10) . . ?
C104 C105 H10G 110.6 . . ?
C104 C105 H10H 110.6 . . ?
H10G C105 H10H 108.8 . . ?
S101 C106 S102 118.17(8) . . ?
N101 C106 S101 106.91(10) . . ?
N101 C106 S102 103.06(9) . . ?
N101 C106 C107 107.20(12) . . ?
C107 C106 S101 117.84(10) . . ?
C107 C106 S102 102.33(9) . . ?
C106 C107 H107 112.1 . . ?
C106 C107 C108 104.53(11) . . ?
C108 C107 H107 112.1 . . ?
C111 C107 C106 110.60(13) . . ?
C111 C107 H107 112.1 . . ?
C111 C107 C108 104.93(11) . . ?
C107 C108 H108 111.5 . . ?
C107 C108 C109 105.51(12) . . ?
C109 C108 H108 111.5 . . ?
C112 C108 C107 104.79(12) . . ?
C112 C108 H108 111.5 . . ?
C112 C108 C109 111.83(11) . . ?
C108 C109 S102 103.72(10) . . ?
C110 C109 S102 100.29(10) . . ?
C110 C109 C108 103.58(11) . . ?
C119 C109 S102 114.12(10) . . ?
C119 C109 C108 116.06(12) . . ?
C119 C109 C110 116.99(12) . . ?
O101 C110 N101 126.14(14) . . ?
O101 C110 C109 127.64(14) . . ?
N101 C110 C109 106.21(12) . . ?
O102 C111 N102 125.24(15) . . ?
O102 C111 C107 126.42(14) . . ?
N102 C111 C107 108.33(13) . . ?
O103 C112 N102 125.07(13) . . ?
O103 C112 C108 127.23(14) . . ?
N102 C112 C108 107.69(12) . . ?
C114 C113 N102 118.57(14) . . ?
C118 C113 N102 119.64(15) . . ?
C118 C113 C114 121.79(14) . . ?
C113 C114 H114 120.7 . . ?
C113 C114 C115 118.69(15) . . ?
C115 C114 H114 120.7 . . ?
C114 C115 H115 119.9 . . ?
C116 C115 C114 120.21(17) . . ?
C116 C115 H115 119.9 . . ?
C115 C116 H116 119.8 . . ?
C117 C116 C115 120.36(15) . . ?
C117 C116 H116 119.8 . . ?
C116 C117 H117 119.8 . . ?
C116 C117 C118 120.36(15) . . ?
C118 C117 H117 119.8 . . ?
C113 C118 C117 118.58(16) . . ?
C113 C118 H118 120.7 . . ?
C117 C118 H118 120.7 . . ?
C120 C119 C109 120.69(14) . . ?
C120 C119 C124 118.92(15) . . ?
C124 C119 C109 120.33(14) . . ?
C119 C120 H120 119.7 . . ?
C121 C120 C119 120.69(16) . . ?
C121 C120 H120 119.7 . . ?
C120 C121 H121 120.0 . . ?
C122 C121 C120 120.00(16) . . ?
C122 C121 H121 120.0 . . ?
C121 C122 H122 120.2 . . ?
C121 C122 C123 119.65(16) . . ?
C123 C122 H122 120.2 . . ?
C122 C123 H123 119.8 . . ?
C122 C123 C124 120.48(16) . . ?
C124 C123 H123 119.8 . . ?
C119 C124 H124 119.9 . . ?
C123 C124 C119 120.26(15) . . ?
C123 C124 H124 119.9 . . ?
C206 S201 C205 91.23(7) . . ?
C209 S202 C206 79.39(6) . . ?
C206 N201 C204 117.70(12) . . ?
C210 N201 C204 126.62(12) . . ?
C210 N201 C206 111.29(12) . . ?
C211 N202 C212 113.21(13) . . ?
C211 N202 C213 122.22(13) . . ?
C212 N202 C213 124.38(13) . . ?
C202 C201 H201 108.6 . . ?
C202 C201 C204 109.61(13) . . ?
C203 C201 H201 108.6 . . ?
C203 C201 C202 110.39(14) . . ?
C203 C201 C204 111.06(12) . . ?
C204 C201 H201 108.6 . . ?
C201 C202 H20A 109.5 . . ?
C201 C202 H20B 109.5 . . ?
C201 C202 H20C 109.5 . . ?
H20A C202 H20B 109.5 . . ?
H20A C202 H20C 109.5 . . ?
H20B C202 H20C 109.5 . . ?
C201 C203 H20D 109.5 . . ?
C201 C203 H20E 109.5 . . ?
C201 C203 H20F 109.5 . . ?
H20D C203 H20E 109.5 . . ?
H20D C203 H20F 109.5 . . ?
H20E C203 H20F 109.5 . . ?
N201 C204 C201 112.81(12) . . ?
N201 C204 H204 108.5 . . ?
N201 C204 C205 104.22(12) . . ?
C201 C204 H204 108.5 . . ?
C205 C204 C201 114.10(12) . . ?
C205 C204 H204 108.5 . . ?
S201 C205 H20G 110.4 . . ?
S201 C205 H20H 110.4 . . ?
C204 C205 S201 106.69(11) . . ?
C204 C205 H20G 110.4 . . ?
C204 C205 H20H 110.4 . . ?
H20G C205 H20H 108.6 . . ?
S201 C206 S202 118.20(8) . . ?
N201 C206 S201 107.08(10) . . ?
N201 C206 S202 103.40(9) . . ?
N201 C206 C207 107.08(12) . . ?
C207 C206 S201 117.53(9) . . ?
C207 C206 S202 102.27(9) . . ?
C206 C207 H207 111.7 . . ?
C206 C207 C208 104.96(11) . . ?
C208 C207 H207 111.7 . . ?
C211 C207 C206 111.22(13) . . ?
C211 C207 H207 111.7 . . ?
C211 C207 C208 105.15(12) . . ?
C207 C208 H208 111.3 . . ?
C207 C208 C209 105.46(12) . . ?
C209 C208 H208 111.3 . . ?
C212 C208 C207 104.75(12) . . ?
C212 C208 H208 111.3 . . ?
C212 C208 C209 112.25(11) . . ?
C208 C209 S202 102.90(9) . . ?
C210 C209 S202 99.81(10) . . ?
C210 C209 C208 105.60(11) . . ?
C219 C209 S202 115.99(10) . . ?
C219 C209 C208 116.40(12) . . ?
C219 C209 C210 114.16(12) . . ?
O201 C210 N201 126.13(14) . . ?
O201 C210 C209 126.78(13) . . ?
N201 C210 C209 107.09(12) . . ?
O202 C211 N202 125.34(14) . . ?
O202 C211 C207 126.05(14) . . ?
N202 C211 C207 108.60(13) . . ?
O203 C212 N202 124.37(14) . . ?
O203 C212 C208 127.69(14) . . ?
N202 C212 C208 107.94(12) . . ?
C214 C213 N202 118.36(15) . . ?
C218 C213 N202 119.99(16) . . ?
C218 C213 C214 121.65(16) . . ?
C213 C214 H214 120.6 . . ?
C215 C214 C213 118.72(18) . . ?
C215 C214 H214 120.6 . . ?
C214 C215 H215 119.8 . . ?
C216 C215 C214 120.3(2) . . ?
C216 C215 H215 119.8 . . ?
C215 C216 H216 119.9 . . ?
C217 C216 C215 120.26(17) . . ?
C217 C216 H216 119.9 . . ?
C216 C217 H217 119.8 . . ?
C216 C217 C218 120.45(19) . . ?
C218 C217 H217 119.8 . . ?
C213 C218 C217 118.59(19) . . ?
C213 C218 H218 120.7 . . ?
C217 C218 H218 120.7 . . ?
C220 C219 C209 121.96(14) . . ?
C220 C219 C224 119.15(14) . . ?
C224 C219 C209 118.89(13) . . ?
C219 C220 H220 119.8 . . ?
C219 C220 C221 120.44(16) . . ?
C221 C220 H220 119.8 . . ?
C220 C221 H221 120.0 . . ?
C222 C221 C220 120.02(15) . . ?
C222 C221 H221 120.0 . . ?
C221 C222 H222 120.1 . . ?
C221 C222 C223 119.89(14) . . ?
C223 C222 H222 120.1 . . ?
C222 C223 H223 119.9 . . ?
C224 C223 C222 120.20(16) . . ?
C224 C223 H223 119.9 . . ?
C219 C224 H224 119.8 . . ?
C223 C224 C219 120.31(14) . . ?
C223 C224 H224 119.8 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_submission    08/11/2014
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id caqnphrfalto
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2015acc0009_k_100k
_database_code_depnum_ccdc_archive 'CCDC 1830933'
_audit_update_record             
;
2018-03-19 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_audit_creation_date             2015-03-23
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H16 N2 O3 S2'
_chemical_formula_sum            'C19 H16 N2 O3 S2'
_chemical_formula_weight         384.46
_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 0.0033 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'
N N 0.0061 0.0033 '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'

_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.4140(3)
_cell_length_b                   15.8099(4)
_cell_length_c                   21.1096(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3475.57(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9202
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.7140
_cell_measurement_theta_min      2.5130
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.329
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1600
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            18670
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.811
_diffrn_reflns_theta_min         1.929
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -109.00   71.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0000    0.0000 -180.0000 180

#__ type_ start__ end____ width___ exp.time_
  2 omega   52.00   62.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0000   72.0000 -120.0000 10

#__ type_ start__ end____ width___ exp.time_
  3 omega -109.00  -77.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.0000    0.0000  120.0000 32
;
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-HF'
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_UB_11      -0.0550570000
_diffrn_orient_matrix_UB_12      0.0124904000
_diffrn_orient_matrix_UB_13      -0.0174137000
_diffrn_orient_matrix_UB_21      -0.0138859000
_diffrn_orient_matrix_UB_22      0.0311486000
_diffrn_orient_matrix_UB_23      0.0231854000
_diffrn_orient_matrix_UB_31      0.0376133000
_diffrn_orient_matrix_UB_32      0.0297811000
_diffrn_orient_matrix_UB_33      -0.0169723000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4044
_reflns_number_total             4978
_reflns_odcompleteness_completeness 91.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.74
_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, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4978
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0377P)²+2.5535P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0948
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C15(H15), C10(H10), C13(H13), C19(H19), C16(H16), C11(H11),
 C18(H18), C17(H17)
;
_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
S2 S 0.90568(4) 0.59671(2) 0.63319(2) 0.01573(9) Uani 1 1 d . . . . .
S1 S 1.03082(4) 0.44020(3) 0.69724(2) 0.01744(9) Uani 1 1 d . . . . .
O1 O 0.83354(11) 0.47085(7) 0.48882(5) 0.0179(2) Uani 1 1 d . . . . .
O3 O 0.76252(12) 0.35856(7) 0.74420(5) 0.0223(3) Uani 1 1 d . . . . .
O2 O 0.68558(13) 0.34058(7) 0.64957(6) 0.0258(3) Uani 1 1 d . . . . .
N1 N 0.90358(12) 0.44158(8) 0.59011(6) 0.0146(3) Uani 1 1 d . . . . .
N2 N 0.73209(13) 0.38467(8) 0.69148(6) 0.0171(3) Uani 1 1 d . . . . .
C8 C 0.72384(15) 0.62865(9) 0.53632(7) 0.0145(3) Uani 1 1 d . . . . .
C6 C 0.67582(14) 0.51687(9) 0.62647(7) 0.0142(3) Uani 1 1 d . . . . .
H6 H 0.6353 0.4706 0.6029 0.017 Uiso 1 1 calc R . . . .
C4 C 0.84129(14) 0.48700(9) 0.54496(7) 0.0145(3) Uani 1 1 d . . . . .
C14 C 0.56975(15) 0.57308(10) 0.65164(7) 0.0147(3) Uani 1 1 d . . . . .
C3 C 0.90110(15) 0.48318(10) 0.65179(7) 0.0146(3) Uani 1 1 d . . . . .
C7 C 0.76205(15) 0.47672(9) 0.67831(7) 0.0141(3) Uani 1 1 d . . . . .
H7 H 0.7552 0.5095 0.7176 0.017 Uiso 1 1 calc R . . . .
C9 C 0.78100(15) 0.70800(10) 0.53227(8) 0.0182(3) Uani 1 1 d . . . . .
H9 H 0.8479 0.7218 0.5596 0.022 Uiso 1 1 calc R . . . .
C5 C 0.77490(14) 0.56204(9) 0.58031(7) 0.0138(3) Uani 1 1 d . . . . .
C1 C 1.10813(15) 0.39790(11) 0.62605(7) 0.0190(3) Uani 1 1 d . . . . .
H1A H 1.1629 0.4402 0.6066 0.023 Uiso 1 1 calc R . . . .
H1B H 1.1597 0.3486 0.6363 0.023 Uiso 1 1 calc R . . . .
C12 C 0.58032(17) 0.66887(11) 0.45152(8) 0.0217(3) Uani 1 1 d . . . . .
H12 H 0.5124 0.6558 0.4246 0.026 Uiso 1 1 calc R . . . .
C15 C 0.59465(16) 0.64656(10) 0.68632(8) 0.0198(3) Uani 1 1 d . . . . .
H15 H 0.6790 0.6620 0.6949 0.024 Uiso 1 1 calc R . . . .
C10 C 0.73941(16) 0.76701(10) 0.48794(8) 0.0218(3) Uani 1 1 d . . . . .
H10 H 0.7788 0.8197 0.4855 0.026 Uiso 1 1 calc R . . . .
C13 C 0.62207(16) 0.60962(10) 0.49568(8) 0.0195(3) Uani 1 1 d . . . . .
H13 H 0.5820 0.5571 0.4981 0.023 Uiso 1 1 calc R . . . .
C2 C 0.99806(15) 0.37416(10) 0.58207(7) 0.0172(3) Uani 1 1 d . . . . .
H2A H 1.0272 0.3713 0.5385 0.021 Uiso 1 1 calc R . . . .
H2B H 0.9619 0.3198 0.5938 0.021 Uiso 1 1 calc R . . . .
C19 C 0.44265(16) 0.55119(11) 0.63983(8) 0.0204(3) Uani 1 1 d . . . . .
H19 H 0.4246 0.5021 0.6172 0.024 Uiso 1 1 calc R . . . .
C16 C 0.49439(17) 0.69665(11) 0.70807(8) 0.0232(4) Uani 1 1 d . . . . .
H16 H 0.5120 0.7453 0.7313 0.028 Uiso 1 1 calc R . . . .
C11 C 0.63935(17) 0.74723(11) 0.44739(8) 0.0223(3) Uani 1 1 d . . . . .
H11 H 0.6118 0.7864 0.4175 0.027 Uiso 1 1 calc R . . . .
C18 C 0.34170(17) 0.60182(12) 0.66137(9) 0.0256(4) Uani 1 1 d . . . . .
H18 H 0.2572 0.5866 0.6528 0.031 Uiso 1 1 calc R . . . .
C17 C 0.36767(18) 0.67452(11) 0.69537(8) 0.0230(4) Uani 1 1 d . . . . .
H17 H 0.3008 0.7085 0.7097 0.028 Uiso 1 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
S2 C3 1.8380(16) . ?
S2 C5 1.8443(15) . ?
S1 C3 1.7909(16) . ?
S1 C1 1.8314(16) . ?
O1 C4 1.2149(18) . ?
O3 N2 1.2286(17) . ?
O2 N2 1.2260(17) . ?
N1 C4 1.3584(19) . ?
N1 C3 1.4589(19) . ?
N1 C2 1.4605(19) . ?
N2 C7 1.514(2) . ?
C8 C9 1.391(2) . ?
C8 C5 1.501(2) . ?
C8 C13 1.396(2) . ?
C6 H6 0.9800 . ?
C6 C14 1.514(2) . ?
C6 C7 1.551(2) . ?
C6 C5 1.589(2) . ?
C4 C5 1.563(2) . ?
C14 C15 1.397(2) . ?
C14 C19 1.391(2) . ?
C3 C7 1.556(2) . ?
C7 H7 0.9800 . ?
C9 H9 0.9300 . ?
C9 C10 1.391(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.522(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.391(2) . ?
C12 C11 1.386(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.389(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.384(2) . ?
C13 H13 0.9300 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C19 H19 0.9300 . ?
C19 C18 1.397(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.391(3) . ?
C11 H11 0.9300 . ?
C18 H18 0.9300 . ?
C18 C17 1.382(3) . ?
C17 H17 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
C3 S2 C5 79.62(7) . . ?
C3 S1 C1 91.75(7) . . ?
C4 N1 C3 112.30(12) . . ?
C4 N1 C2 128.76(12) . . ?
C3 N1 C2 116.40(12) . . ?
O3 N2 C7 115.86(13) . . ?
O2 N2 O3 124.36(14) . . ?
O2 N2 C7 119.70(12) . . ?
C9 C8 C5 121.26(14) . . ?
C9 C8 C13 118.77(14) . . ?
C13 C8 C5 119.85(14) . . ?
C14 C6 H6 107.6 . . ?
C14 C6 C7 114.52(12) . . ?
C14 C6 C5 115.17(12) . . ?
C7 C6 H6 107.6 . . ?
C7 C6 C5 103.92(12) . . ?
C5 C6 H6 107.6 . . ?
O1 C4 N1 127.23(14) . . ?
O1 C4 C5 126.58(14) . . ?
N1 C4 C5 106.11(12) . . ?
C15 C14 C6 122.44(14) . . ?
C19 C14 C6 119.03(14) . . ?
C19 C14 C15 118.52(14) . . ?
S1 C3 S2 117.73(8) . . ?
N1 C3 S2 104.43(10) . . ?
N1 C3 S1 107.08(10) . . ?
N1 C3 C7 107.94(12) . . ?
C7 C3 S2 99.50(10) . . ?
C7 C3 S1 118.97(10) . . ?
N2 C7 C6 113.80(12) . . ?
N2 C7 C3 108.72(12) . . ?
N2 C7 H7 109.7 . . ?
C6 C7 C3 104.96(11) . . ?
C6 C7 H7 109.7 . . ?
C3 C7 H7 109.7 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.87(15) . . ?
C10 C9 H9 119.6 . . ?
C8 C5 S2 115.30(11) . . ?
C8 C5 C6 117.69(12) . . ?
C8 C5 C4 113.19(12) . . ?
C6 C5 S2 104.01(9) . . ?
C4 C5 S2 100.83(10) . . ?
C4 C5 C6 103.83(11) . . ?
S1 C1 H1A 110.7 . . ?
S1 C1 H1B 110.7 . . ?
H1A C1 H1B 108.8 . . ?
C2 C1 S1 105.04(10) . . ?
C2 C1 H1A 110.7 . . ?
C2 C1 H1B 110.7 . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.36(16) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.52(16) . . ?
C16 C15 H15 119.7 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 119.93(15) . . ?
C11 C10 H10 120.0 . . ?
C8 C13 H13 119.9 . . ?
C12 C13 C8 120.25(15) . . ?
C12 C13 H13 119.9 . . ?
N1 C2 C1 104.86(12) . . ?
N1 C2 H2A 110.8 . . ?
N1 C2 H2B 110.8 . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
C14 C19 H19 119.5 . . ?
C14 C19 C18 121.01(16) . . ?
C18 C19 H19 119.5 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.40(16) . . ?
C17 C16 H16 119.8 . . ?
C12 C11 H11 120.1 . . ?
C10 C11 C12 119.81(15) . . ?
C10 C11 H11 120.1 . . ?
C19 C18 H18 120.1 . . ?
C17 C18 C19 119.88(17) . . ?
C17 C18 H18 120.1 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.67(16) . . ?
C18 C17 H17 120.2 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id caNO2
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2015acc0007
_database_code_depnum_ccdc_archive 'CCDC 1830931'
_audit_update_record             
;
2018-03-19 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_audit_creation_date             2015-02-20
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H12 N2 O S2'
_chemical_formula_sum            'C14 H12 N2 O S2'
_chemical_formula_weight         288.38
_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 0.0033 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'
N N 0.0061 0.0033 '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'

_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.3634(2)
_cell_length_b                   12.0468(3)
_cell_length_c                   21.0449(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2627.36(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    15838
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.8640
_cell_measurement_theta_min      1.9120
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.397
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90161
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1200
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            24439
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.984
_diffrn_reflns_theta_min         1.935
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -112.00   50.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000    0.0000  120.0000 162

#__ type_ start__ end____ width___ exp.time_
  2 omega  -26.00   68.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000   72.0000  -60.0000 94

#__ type_ start__ end____ width___ exp.time_
  3 omega -112.00  -10.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000    0.0000    0.0000 102
;
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-HF'
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_UB_11      -0.0402973000
_diffrn_orient_matrix_UB_12      0.0302395000
_diffrn_orient_matrix_UB_13      -0.0210337000
_diffrn_orient_matrix_UB_21      0.0172891000
_diffrn_orient_matrix_UB_22      -0.0362852000
_diffrn_orient_matrix_UB_23      -0.0251164000
_diffrn_orient_matrix_UB_31      -0.0525661000
_diffrn_orient_matrix_UB_32      -0.0351856000
_diffrn_orient_matrix_UB_33      0.0078470000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3840
_reflns_number_total             4330
_reflns_odcompleteness_completeness 95.19
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.91
_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, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         4330
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0298
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0442P)²+0.9514P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0798
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
;
_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
S1 S 0.38608(2) 0.71852(2) 0.65882(2) 0.01517(7) Uani 1 1 d . . . . .
S2 S 0.42720(2) 0.50002(2) 0.57980(2) 0.01342(6) Uani 1 1 d . . . . .
O1 O 0.74780(7) 0.45720(7) 0.65705(3) 0.01751(15) Uani 1 1 d . . . . .
N1 N 0.57757(7) 0.57810(7) 0.66780(4) 0.01353(15) Uani 1 1 d . . . . .
N2 N 0.12654(9) 0.49493(8) 0.69102(5) 0.01979(18) Uani 1 1 d . . . . .
C1 C 0.63799(10) 0.68683(9) 0.67401(5) 0.01736(18) Uani 1 1 d . . . . .
H1A H 0.7232 0.6869 0.6549 0.021 Uiso 1 1 calc R . . . .
H1B H 0.6458 0.7076 0.7184 0.021 Uiso 1 1 calc R . . . .
C2 C 0.54811(10) 0.76644(9) 0.63887(5) 0.01895(19) Uani 1 1 d . . . . .
H2A H 0.5626 0.7629 0.5934 0.023 Uiso 1 1 calc R . . . .
H2B H 0.5612 0.8422 0.6531 0.023 Uiso 1 1 calc R . . . .
C3 C 0.43907(9) 0.57716(8) 0.65534(4) 0.01224(16) Uani 1 1 d . . . . .
C4 C 0.37757(9) 0.49615(8) 0.70402(5) 0.01324(17) Uani 1 1 d . . . . .
H4 H 0.4016 0.5175 0.7474 0.016 Uiso 1 1 calc R . . . .
C5 C 0.43793(9) 0.38138(8) 0.68699(5) 0.01385(17) Uani 1 1 d . . . . .
H5A H 0.4889 0.3534 0.7222 0.017 Uiso 1 1 calc R . . . .
H5B H 0.3709 0.3278 0.6772 0.017 Uiso 1 1 calc R . . . .
C6 C 0.52470(9) 0.40209(8) 0.62795(4) 0.01237(16) Uani 1 1 d . . . . .
C7 C 0.63411(9) 0.48029(8) 0.65153(4) 0.01321(17) Uani 1 1 d . . . . .
C8 C 0.23638(10) 0.49534(8) 0.69726(5) 0.01498(18) Uani 1 1 d . . . . .
C9 C 0.56943(9) 0.30215(8) 0.59129(5) 0.01440(17) Uani 1 1 d . . . . .
C10 C 0.51827(10) 0.19666(8) 0.60192(5) 0.01830(19) Uani 1 1 d . . . . .
H10 H 0.4567 0.1865 0.6335 0.022 Uiso 1 1 calc R . . . .
C11 C 0.55870(11) 0.10645(9) 0.56556(6) 0.0225(2) Uani 1 1 d . . . . .
H11 H 0.5237 0.0365 0.5729 0.027 Uiso 1 1 calc R . . . .
C12 C 0.65104(11) 0.12066(9) 0.51847(5) 0.0227(2) Uani 1 1 d . . . . .
H12 H 0.6773 0.0605 0.4940 0.027 Uiso 1 1 calc R . . . .
C13 C 0.70412(11) 0.22491(9) 0.50800(5) 0.0204(2) Uani 1 1 d . . . . .
H13 H 0.7667 0.2343 0.4768 0.025 Uiso 1 1 calc R . . . .
C14 C 0.66388(10) 0.31550(9) 0.54416(5) 0.01718(18) Uani 1 1 d . . . . .
H14 H 0.6998 0.3851 0.5370 0.021 Uiso 1 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 C2 1.8246(11) . ?
S1 C3 1.7908(10) . ?
S2 C3 1.8454(9) . ?
S2 C6 1.8546(9) . ?
O1 C7 1.2161(12) . ?
N1 C1 1.4576(13) . ?
N1 C3 1.4592(12) . ?
N1 C7 1.3597(12) . ?
N2 C8 1.1459(14) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.5278(15) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.5518(13) . ?
C4 H4 0.9800 . ?
C4 C5 1.5592(13) . ?
C4 C8 1.4701(14) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.5539(13) . ?
C6 C7 1.5554(13) . ?
C6 C9 1.5033(13) . ?
C9 C10 1.3950(14) . ?
C9 C14 1.4027(14) . ?
C10 H10 0.9300 . ?
C10 C11 1.3935(15) . ?
C11 H11 0.9300 . ?
C11 C12 1.3882(16) . ?
C12 H12 0.9300 . ?
C12 C13 1.3887(16) . ?
C13 H13 0.9300 . ?
C13 C14 1.3942(14) . ?
C14 H14 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
C3 S1 C2 90.53(5) . . ?
C3 S2 C6 79.24(4) . . ?
C1 N1 C3 116.46(8) . . ?
C7 N1 C1 128.04(8) . . ?
C7 N1 C3 111.83(8) . . ?
N1 C1 H1A 110.7 . . ?
N1 C1 H1B 110.7 . . ?
N1 C1 C2 105.00(8) . . ?
H1A C1 H1B 108.8 . . ?
C2 C1 H1A 110.7 . . ?
C2 C1 H1B 110.7 . . ?
S1 C2 H2A 110.8 . . ?
S1 C2 H2B 110.8 . . ?
C1 C2 S1 104.54(7) . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
S1 C3 S2 119.58(5) . . ?
N1 C3 S1 106.67(6) . . ?
N1 C3 S2 102.96(6) . . ?
N1 C3 C4 106.88(7) . . ?
C4 C3 S1 116.43(6) . . ?
C4 C3 S2 102.98(6) . . ?
C3 C4 H4 110.2 . . ?
C3 C4 C5 103.95(7) . . ?
C5 C4 H4 110.2 . . ?
C8 C4 C3 110.43(8) . . ?
C8 C4 H4 110.2 . . ?
C8 C4 C5 111.79(8) . . ?
C4 C5 H5A 110.6 . . ?
C4 C5 H5B 110.6 . . ?
H5A C5 H5B 108.7 . . ?
C6 C5 C4 105.88(7) . . ?
C6 C5 H5A 110.6 . . ?
C6 C5 H5B 110.6 . . ?
C5 C6 S2 102.93(6) . . ?
C5 C6 C7 105.31(7) . . ?
C7 C6 S2 100.73(6) . . ?
C9 C6 S2 113.39(6) . . ?
C9 C6 C5 117.40(8) . . ?
C9 C6 C7 115.09(8) . . ?
O1 C7 N1 126.27(9) . . ?
O1 C7 C6 126.74(9) . . ?
N1 C7 C6 106.92(8) . . ?
N2 C8 C4 178.95(11) . . ?
C10 C9 C6 122.01(9) . . ?
C10 C9 C14 118.88(9) . . ?
C14 C9 C6 119.09(9) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.54(10) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.20(10) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.86(10) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.18(10) . . ?
C14 C13 H13 119.9 . . ?
C9 C14 H14 119.8 . . ?
C13 C14 C9 120.33(10) . . ?
C13 C14 H14 119.8 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_submission    2015-02-18
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id AcrCN-bajo
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2015acc0008
_database_code_depnum_ccdc_archive 'CCDC 1830932'
_audit_update_record             
;
2018-03-19 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_audit_creation_date             2015-03-03
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H12 N2 O S2'
_chemical_formula_sum            'C14 H12 N2 O S2'
_chemical_formula_weight         288.38
_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 0.0033 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'
N N 0.0061 0.0033 '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'

_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                   5.6439(3)
_cell_length_b                   10.3733(3)
_cell_length_c                   11.1733(4)
_cell_angle_alpha                88.811(3)
_cell_angle_beta                 76.205(4)
_cell_angle_gamma                88.281(3)
_cell_volume                     634.93(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8494
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.1200
_cell_measurement_theta_min      2.7230
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.411
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             300
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12461
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.334
_diffrn_reflns_theta_min         2.698
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -39.00   67.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0000   72.0000  150.0000 106

#__ type_ start__ end____ width___ exp.time_
  2 omega  -73.00   15.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0000  -72.0000   30.0000 88

#__ type_ start__ end____ width___ exp.time_
  3 omega  -73.00   16.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0000  -72.0000 -150.0000 89

#__ type_ start__ end____ width___ exp.time_
  4 omega  -68.00   11.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0000    0.0000 -180.0000 79

#__ type_ start__ end____ width___ exp.time_
  5 omega  -38.00   -9.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0000   54.0000    0.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega  -62.00  -52.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0000   72.0000  120.0000 10

#__ type_ start__ end____ width___ exp.time_
  7 omega -113.00   67.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0000    0.0000 -150.0000 180

#__ type_ start__ end____ width___ exp.time_
  8 omega  -60.00   16.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0000  -72.0000    0.0000 76

#__ type_ start__ end____ width___ exp.time_
  9 omega  -69.00   16.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0000  -72.0000 -180.0000 85
;
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-VHF'
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_UB_11      0.0706167000
_diffrn_orient_matrix_UB_12      -0.0228365000
_diffrn_orient_matrix_UB_13      0.0411124000
_diffrn_orient_matrix_UB_21      -0.0611902000
_diffrn_orient_matrix_UB_22      -0.0593985000
_diffrn_orient_matrix_UB_23      0.0065626000
_diffrn_orient_matrix_UB_31      0.0895932000
_diffrn_orient_matrix_UB_32      -0.0251180000
_diffrn_orient_matrix_UB_33      -0.0504025000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3796
_reflns_number_total             4143
_reflns_odcompleteness_completeness 91.28
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.26
_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, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         4143
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0313
_refine_ls_restrained_S_all      1.043
_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)+(0.0532P)²+0.1930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0864
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
;
_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
S1 S 0.18748(5) 0.90355(2) 0.58347(2) 0.01834(7) Uani 1 1 d . . . . .
S2 S -0.00779(4) 0.64516(2) 0.70462(2) 0.01601(7) Uani 1 1 d . . . . .
O1 O 0.60053(13) 0.48930(7) 0.61622(6) 0.01446(13) Uani 1 1 d . . . . .
N1 N 0.45051(15) 0.69904(8) 0.61776(7) 0.01228(15) Uani 1 1 d . . . . .
N2 N 0.62114(19) 0.93334(9) 0.81789(9) 0.02246(19) Uani 1 1 d . . . . .
C1 C 0.3836(2) 0.82436(10) 0.44973(10) 0.0212(2) Uani 1 1 d . . . . .
H1A H 0.2920 0.7642 0.4143 0.025 Uiso 1 1 calc R . . . .
H1B H 0.4549 0.8873 0.3871 0.025 Uiso 1 1 calc R . . . .
C2 C 0.57994(19) 0.75396(10) 0.49979(9) 0.01682(18) Uani 1 1 d . . . . .
H2A H 0.6592 0.6866 0.4442 0.020 Uiso 1 1 calc R . . . .
H2B H 0.7022 0.8132 0.5111 0.020 Uiso 1 1 calc R . . . .
C3 C 0.22681(17) 0.76808(9) 0.67997(9) 0.01330(16) Uani 1 1 d . . . . .
C4 C 0.4568(2) 0.87199(9) 0.81523(9) 0.01629(18) Uani 1 1 d . . . . .
C5 C 0.24592(18) 0.79291(9) 0.81351(9) 0.01409(17) Uani 1 1 d . . . . .
H5 H 0.0958 0.8360 0.8595 0.017 Uiso 1 1 calc R . . . .
C6 C 0.26767(19) 0.65395(9) 0.86720(8) 0.01447(17) Uani 1 1 d . . . . .
H6A H 0.4278 0.6388 0.8832 0.017 Uiso 1 1 calc R . . . .
H6B H 0.1452 0.6421 0.9436 0.017 Uiso 1 1 calc R . . . .
C7 C 0.22677(16) 0.56032(8) 0.76715(8) 0.01119(15) Uani 1 1 d . . . . .
C8 C 0.45089(17) 0.57338(9) 0.65632(8) 0.01124(16) Uani 1 1 d . . . . .
C9 C 0.17567(17) 0.42307(8) 0.80805(8) 0.01165(16) Uani 1 1 d . . . . .
C10 C -0.00919(18) 0.35639(9) 0.77525(9) 0.01438(17) Uani 1 1 d . . . . .
H10 H -0.1087 0.3982 0.7305 0.017 Uiso 1 1 calc R . . . .
C11 C -0.04583(19) 0.22681(9) 0.80934(9) 0.01674(18) Uani 1 1 d . . . . .
H11 H -0.1705 0.1829 0.7878 0.020 Uiso 1 1 calc R . . . .
C12 C 0.10296(19) 0.16367(9) 0.87508(9) 0.01657(18) Uani 1 1 d . . . . .
H12 H 0.0786 0.0773 0.8973 0.020 Uiso 1 1 calc R . . . .
C13 C 0.2886(2) 0.22912(10) 0.90785(10) 0.01790(19) Uani 1 1 d . . . . .
H13 H 0.3890 0.1866 0.9518 0.021 Uiso 1 1 calc R . . . .
C14 C 0.32398(18) 0.35860(9) 0.87473(9) 0.01604(18) Uani 1 1 d . . . . .
H14 H 0.4476 0.4025 0.8973 0.019 Uiso 1 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 C1 1.8278(12) . ?
S1 C3 1.7942(9) . ?
S2 C3 1.8350(9) . ?
S2 C7 1.8333(9) . ?
O1 C8 1.2110(11) . ?
N1 C2 1.4595(12) . ?
N1 C3 1.4621(12) . ?
N1 C8 1.3645(12) . ?
N2 C4 1.1469(14) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.5178(16) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C5 1.5487(14) . ?
C4 C5 1.4697(14) . ?
C5 H5 0.9800 . ?
C5 C6 1.5625(13) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.5582(13) . ?
C7 C8 1.5518(13) . ?
C7 C9 1.5012(12) . ?
C9 C10 1.3920(13) . ?
C9 C14 1.3951(13) . ?
C10 H10 0.9300 . ?
C10 C11 1.3973(13) . ?
C11 H11 0.9300 . ?
C11 C12 1.3839(15) . ?
C12 H12 0.9300 . ?
C12 C13 1.3888(15) . ?
C13 H13 0.9300 . ?
C13 C14 1.3931(13) . ?
C14 H14 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
C3 S1 C1 90.57(5) . . ?
C7 S2 C3 79.54(4) . . ?
C2 N1 C3 115.83(8) . . ?
C8 N1 C2 127.87(8) . . ?
C8 N1 C3 111.43(7) . . ?
S1 C1 H1A 110.8 . . ?
S1 C1 H1B 110.8 . . ?
H1A C1 H1B 108.9 . . ?
C2 C1 S1 104.72(7) . . ?
C2 C1 H1A 110.8 . . ?
C2 C1 H1B 110.8 . . ?
N1 C2 C1 104.78(8) . . ?
N1 C2 H2A 110.8 . . ?
N1 C2 H2B 110.8 . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
S1 C3 S2 116.71(5) . . ?
N1 C3 S1 107.10(6) . . ?
N1 C3 S2 104.09(6) . . ?
N1 C3 C5 107.28(7) . . ?
C5 C3 S1 118.75(7) . . ?
C5 C3 S2 101.71(6) . . ?
N2 C4 C5 179.26(11) . . ?
C3 C5 H5 109.7 . . ?
C3 C5 C6 103.16(7) . . ?
C4 C5 C3 111.38(8) . . ?
C4 C5 H5 109.7 . . ?
C4 C5 C6 112.87(8) . . ?
C6 C5 H5 109.7 . . ?
C5 C6 H6A 110.6 . . ?
C5 C6 H6B 110.6 . . ?
H6A C6 H6B 108.7 . . ?
C7 C6 C5 105.80(7) . . ?
C7 C6 H6A 110.6 . . ?
C7 C6 H6B 110.6 . . ?
C6 C7 S2 103.14(6) . . ?
C8 C7 S2 100.25(6) . . ?
C8 C7 C6 106.23(7) . . ?
C9 C7 S2 116.05(6) . . ?
C9 C7 C6 116.19(7) . . ?
C9 C7 C8 113.20(7) . . ?
O1 C8 N1 127.40(9) . . ?
O1 C8 C7 126.28(8) . . ?
N1 C8 C7 106.26(8) . . ?
C10 C9 C7 121.27(8) . . ?
C10 C9 C14 119.09(8) . . ?
C14 C9 C7 119.55(8) . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.27(9) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.15(9) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.06(9) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.81(9) . . ?
C14 C13 H13 120.1 . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.61(9) . . ?
C13 C14 H14 119.7 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_submission    2015-03-02
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id acrCNalto
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2014acc0006
_database_code_depnum_ccdc_archive 'CCDC 1830929'
_audit_update_record             
;
2018-03-19 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_audit_creation_date             2014-11-11
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.11.07 svn.r3078 for OlexSys, GUI svn.r4941)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H21 N O3 S2'
_chemical_formula_sum            'C19 H21 N O3 S2'
_chemical_formula_weight         375.49
_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 0.0033 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'
N N 0.0061 0.0033 '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'

_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.13571(13)
_cell_length_b                   13.38135(18)
_cell_length_c                   30.0335(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3671.54(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    30472
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.8930
_cell_measurement_theta_min      2.2170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       slab
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            40740
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.963
_diffrn_reflns_theta_min         2.713
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -112.00   39.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000  -18.0000   90.0000 151

#__ type_ start__ end____ width___ exp.time_
  2 omega -111.00  -14.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000  -72.0000   90.0000 97

#__ type_ start__ end____ width___ exp.time_
  3 omega  -61.00  -51.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000    0.0000 -180.0000 10

#__ type_ start__ end____ width___ exp.time_
  4 omega -112.00   50.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000    0.0000   60.0000 162

#__ type_ start__ end____ width___ exp.time_
  5 omega  -68.00  -57.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000  -72.0000  150.0000 11
;
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-HF'
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_UB_11      0.0234996000
_diffrn_orient_matrix_UB_12      0.0113344000
_diffrn_orient_matrix_UB_13      0.0219316000
_diffrn_orient_matrix_UB_21      -0.0327278000
_diffrn_orient_matrix_UB_22      0.0479171000
_diffrn_orient_matrix_UB_23      -0.0016647000
_diffrn_orient_matrix_UB_31      -0.0664000000
_diffrn_orient_matrix_UB_32      -0.0196067000
_diffrn_orient_matrix_UB_33      0.0085880000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5697
_reflns_number_total             6097
_reflns_odcompleteness_completeness 95.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.97
_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, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_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    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         6097
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0296
_refine_ls_restrained_S_all      1.042
_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)+(0.0436P)²+1.4444P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0815
_refine_special_details          ?
_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:
 C1(H1A,H1B), C2(H2A,H2B), C5(H5A,H5B), C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C19(H19A,H19B,H19C)
;
_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
S1 S 0.35906(2) 0.24369(2) 0.48429(2) 0.01480(6) Uani 1 1 d . . . . .
S2 S 0.56595(2) 0.32547(2) 0.33632(2) 0.01491(6) Uani 1 1 d . . . . .
O1 O 0.29918(8) 0.43932(5) 0.47466(2) 0.01942(13) Uani 1 1 d . . . . .
O2 O 0.76562(7) 0.15823(5) 0.38945(2) 0.01556(12) Uani 1 1 d . . . . .
O3 O 0.71652(8) 0.08851(6) 0.23858(3) 0.02805(17) Uani 1 1 d . . . . .
N1 N 0.59134(8) 0.21742(5) 0.43576(2) 0.01241(13) Uani 1 1 d . . . . .
C1 C 0.45342(10) 0.12346(6) 0.48886(3) 0.01615(15) Uani 1 1 d . . . . .
H1A H 0.5113 0.1211 0.5159 0.019 Uiso 1 1 calc R . . . .
H1B H 0.3831 0.0691 0.4895 0.019 Uiso 1 1 calc R . . . .
C2 C 0.55133(10) 0.11458(6) 0.44834(3) 0.01536(15) Uani 1 1 d . . . . .
H2A H 0.6382 0.0760 0.4554 0.018 Uiso 1 1 calc R . . . .
H2B H 0.4998 0.0819 0.4242 0.018 Uiso 1 1 calc R . . . .
C3 C 0.49572(9) 0.29158(6) 0.44984(3) 0.01189(14) Uani 1 1 d . . . . .
C4 C 0.51345(9) 0.38902(6) 0.43771(3) 0.01267(14) Uani 1 1 d . . . . .
C5 C 0.65161(9) 0.41562(6) 0.41303(3) 0.01347(14) Uani 1 1 d . . . . .
H5A H 0.7284 0.4293 0.4345 0.016 Uiso 1 1 calc R . . . .
H5B H 0.6349 0.4763 0.3961 0.016 Uiso 1 1 calc R . . . .
C6 C 0.70412(9) 0.33315(6) 0.38111(3) 0.01263(14) Uani 1 1 d . . . . .
C7 C 0.69468(9) 0.22985(6) 0.40236(3) 0.01229(14) Uani 1 1 d . . . . .
C8 C 0.40802(9) 0.46345(6) 0.45249(3) 0.01386(14) Uani 1 1 d . . . . .
C9 C 0.43395(11) 0.57093(7) 0.43999(3) 0.01932(17) Uani 1 1 d . . . . .
H9A H 0.4252 0.5784 0.4083 0.029 Uiso 1 1 calc GR . . . .
H9B H 0.5304 0.5905 0.4492 0.029 Uiso 1 1 calc GR . . . .
H9C H 0.3627 0.6125 0.4545 0.029 Uiso 1 1 calc GR . . . .
C10 C 0.85794(9) 0.35834(6) 0.36512(3) 0.01445(15) Uani 1 1 d . . . . .
C11 C 0.97966(10) 0.32473(7) 0.38912(3) 0.01792(16) Uani 1 1 d . . . . .
H11 H 0.9661 0.2833 0.4136 0.022 Uiso 1 1 calc R . . . .
C12 C 1.12097(11) 0.35254(8) 0.37680(4) 0.02329(19) Uani 1 1 d . . . . .
H12 H 1.2009 0.3295 0.3930 0.028 Uiso 1 1 calc R . . . .
C13 C 1.14247(11) 0.41482(8) 0.34028(4) 0.0258(2) Uani 1 1 d . . . . .
H13 H 1.2367 0.4328 0.3317 0.031 Uiso 1 1 calc R . . . .
C14 C 1.02231(11) 0.44992(8) 0.31670(4) 0.0250(2) Uani 1 1 d . . . . .
H14 H 1.0363 0.4923 0.2925 0.030 Uiso 1 1 calc R . . . .
C15 C 0.88050(10) 0.42209(7) 0.32891(3) 0.02001(17) Uani 1 1 d . . . . .
H15 H 0.8008 0.4461 0.3129 0.024 Uiso 1 1 calc R . . . .
C16 C 0.64684(10) 0.23263(8) 0.29980(3) 0.02020(18) Uani 1 1 d . . . . .
H16A H 0.7417 0.2557 0.2895 0.024 Uiso 1 1 calc R . . . .
H16B H 0.6609 0.1706 0.3159 0.024 Uiso 1 1 calc R . . . .
C17 C 0.54690(10) 0.21508(7) 0.26026(3) 0.01854(16) Uani 1 1 d . . . . .
H17A H 0.4500 0.1976 0.2709 0.022 Uiso 1 1 calc R . . . .
H17B H 0.5387 0.2764 0.2432 0.022 Uiso 1 1 calc R . . . .
C18 C 0.60339(10) 0.13242(7) 0.23031(3) 0.01712(16) Uani 1 1 d . . . . .
C19 C 0.51116(12) 0.10711(8) 0.19068(3) 0.0246(2) Uani 1 1 d . . . . .
H19A H 0.5009 0.1651 0.1721 0.037 Uiso 1 1 calc GR . . . .
H19B H 0.4163 0.0854 0.2005 0.037 Uiso 1 1 calc GR . . . .
H19C H 0.5572 0.0545 0.1740 0.037 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
S1 C1 1.8304(9) . ?
S1 C3 1.7435(8) . ?
S2 C6 1.8475(8) . ?
S2 C16 1.8145(9) . ?
O1 C8 1.2394(11) . ?
O2 C7 1.2201(10) . ?
O3 C18 1.2145(12) . ?
N1 C2 1.4730(10) . ?
N1 C3 1.3880(10) . ?
N1 C7 1.3876(10) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.5150(12) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.3634(11) . ?
C4 C5 1.5064(11) . ?
C4 C8 1.4549(11) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.5385(11) . ?
C6 C7 1.5249(11) . ?
C6 C10 1.5227(12) . ?
C8 C9 1.5052(12) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.3993(12) . ?
C10 C15 1.3976(12) . ?
C11 H11 0.9300 . ?
C11 C12 1.3936(13) . ?
C12 H12 0.9300 . ?
C12 C13 1.3915(15) . ?
C13 H13 0.9300 . ?
C13 C14 1.3882(15) . ?
C14 H14 0.9300 . ?
C14 C15 1.3970(13) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.5163(13) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.5163(13) . ?
C18 C19 1.4971(13) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C3 S1 C1 91.74(4) . . ?
C16 S2 C6 101.53(4) . . ?
C3 N1 C2 115.70(7) . . ?
C7 N1 C2 117.79(7) . . ?
C7 N1 C3 124.24(7) . . ?
S1 C1 H1A 110.4 . . ?
S1 C1 H1B 110.4 . . ?
H1A C1 H1B 108.6 . . ?
C2 C1 S1 106.66(6) . . ?
C2 C1 H1A 110.4 . . ?
C2 C1 H1B 110.4 . . ?
N1 C2 C1 106.22(7) . . ?
N1 C2 H2A 110.5 . . ?
N1 C2 H2B 110.5 . . ?
C1 C2 H2A 110.5 . . ?
C1 C2 H2B 110.5 . . ?
H2A C2 H2B 108.7 . . ?
N1 C3 S1 111.63(6) . . ?
C4 C3 S1 126.52(6) . . ?
C4 C3 N1 121.84(7) . . ?
C3 C4 C5 117.19(7) . . ?
C3 C4 C8 119.64(7) . . ?
C8 C4 C5 122.90(7) . . ?
C4 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
C4 C5 C6 113.48(7) . . ?
H5A C5 H5B 107.7 . . ?
C6 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C5 C6 S2 106.29(5) . . ?
C7 C6 S2 102.46(5) . . ?
C7 C6 C5 111.83(7) . . ?
C10 C6 S2 114.41(6) . . ?
C10 C6 C5 108.99(7) . . ?
C10 C6 C7 112.63(7) . . ?
O2 C7 N1 119.79(8) . . ?
O2 C7 C6 123.30(7) . . ?
N1 C7 C6 116.72(7) . . ?
O1 C8 C4 121.11(8) . . ?
O1 C8 C9 120.61(8) . . ?
C4 C8 C9 118.28(7) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C6 119.99(8) . . ?
C15 C10 C6 121.11(8) . . ?
C15 C10 C11 118.67(8) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 120.91(9) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.00(9) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.55(9) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.61(9) . . ?
C15 C14 H14 119.7 . . ?
C10 C15 H15 119.9 . . ?
C14 C15 C10 120.25(9) . . ?
C14 C15 H15 119.9 . . ?
S2 C16 H16A 109.8 . . ?
S2 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?
C17 C16 S2 109.52(6) . . ?
C17 C16 H16A 109.8 . . ?
C17 C16 H16B 109.8 . . ?
C16 C17 H17A 109.2 . . ?
C16 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 C16 111.88(7) . . ?
C18 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
O3 C18 C17 121.42(8) . . ?
O3 C18 C19 122.15(9) . . ?
C19 C18 C17 116.43(8) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_submission    06/11/2014
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id mvcrfbajo
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2014acc0003
_database_code_depnum_ccdc_archive 'CCDC 1830927'
_audit_update_record             
;
2018-03-19 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_audit_creation_date             2014-04-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C21 H16 N2 O3 S2'
_chemical_formula_sum            'C21 H16 N2 O3 S2'
_chemical_formula_weight         408.48
_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 0.0033 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'
N N 0.0061 0.0033 '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'

_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                   11.8815(12)
_cell_length_b                   6.2795(6)
_cell_length_c                   23.859(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.940(3)
_cell_angle_gamma                90
_cell_volume                     1770.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4324
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.328
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            15920
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.531
_diffrn_reflns_theta_min         2.555
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  Kat
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.075657
_diffrn_orient_matrix_UB_12      -0.025836
_diffrn_orient_matrix_UB_13      -0.027728
_diffrn_orient_matrix_UB_21      0.024494
_diffrn_orient_matrix_UB_22      -0.076089
_diffrn_orient_matrix_UB_23      0.137734
_diffrn_orient_matrix_UB_31      -0.013731
_diffrn_orient_matrix_UB_32      -0.035856
_diffrn_orient_matrix_UB_33      -0.017366
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3608
_reflns_number_total             4058
_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       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_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    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4058
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0294
_refine_ls_restrained_S_all      1.058
_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)+(0.0435P)²+0.5158P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0810
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C17(H17), C14(H14), C12(H12), C13(H13), C19(H19), C21(H21),
 C18(H18), C15(H15), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
S2 S 0.24891(3) 0.93101(5) 0.58944(2) 0.01913(9) Uani 1 1 d . . . . .
S1 S 0.36718(3) 0.98109(6) 0.48183(2) 0.02532(10) Uani 1 1 d . . . . .
O1 O -0.01458(7) 0.74439(14) 0.50687(4) 0.01929(19) Uani 1 1 d . . . . .
O3 O 0.25518(7) 0.36761(15) 0.67074(4) 0.02083(19) Uani 1 1 d . . . . .
O2 O 0.51793(8) 0.62632(17) 0.56190(4) 0.0288(2) Uani 1 1 d . . . . .
N2 N 0.40656(9) 0.46030(17) 0.62240(5) 0.0188(2) Uani 1 1 d . . . . .
N1 N 0.16916(8) 0.80402(18) 0.48866(4) 0.0188(2) Uani 1 1 d . . . . .
C8 C 0.42639(11) 0.5660(2) 0.57284(6) 0.0208(3) Uani 1 1 d . . . . .
C11 C 0.54516(11) 0.5309(2) 0.70366(6) 0.0218(3) Uani 1 1 d . . . . .
H11 H 0.5141 0.6692 0.7070 0.026 Uiso 1 1 calc R . . . .
C16 C 0.06331(10) 0.7075(2) 0.62611(5) 0.0182(2) Uani 1 1 d . . . . .
C4 C 0.08639(10) 0.75542(19) 0.52155(5) 0.0169(2) Uani 1 1 d . . . . .
C6 C 0.22349(10) 0.5124(2) 0.57495(5) 0.0166(2) Uani 1 1 d . . . . .
H6 H 0.1781 0.3922 0.5568 0.020 Uiso 1 1 calc R . . . .
C2 C 0.15850(11) 0.9138(2) 0.43445(5) 0.0200(3) Uani 1 1 d . . . . .
H2A H 0.0806 0.9684 0.4252 0.024 Uiso 1 1 calc R . . . .
H2B H 0.1771 0.8170 0.4040 0.024 Uiso 1 1 calc R . . . .
C3 C 0.28021(10) 0.8180(2) 0.52133(5) 0.0194(3) Uani 1 1 d . . . . .
C5 C 0.14608(10) 0.71132(19) 0.58228(5) 0.0165(2) Uani 1 1 d . . . . .
C10 C 0.49882(10) 0.3919(2) 0.66244(5) 0.0185(2) Uani 1 1 d . . . . .
C17 C -0.01267(11) 0.5387(2) 0.62717(6) 0.0232(3) Uani 1 1 d . . . . .
H17 H -0.0069 0.4198 0.6030 0.028 Uiso 1 1 calc R . . . .
C9 C 0.29163(10) 0.43835(19) 0.62918(5) 0.0173(2) Uani 1 1 d . . . . .
C14 C 0.63560(11) 0.1254(2) 0.69328(6) 0.0251(3) Uani 1 1 d . . . . .
H14 H 0.6666 -0.0129 0.6899 0.030 Uiso 1 1 calc R . . . .
C12 C 0.63777(11) 0.4652(2) 0.74003(6) 0.0240(3) Uani 1 1 d . . . . .
H12 H 0.6700 0.5587 0.7686 0.029 Uiso 1 1 calc R . . . .
C13 C 0.68309(11) 0.2636(2) 0.73466(6) 0.0248(3) Uani 1 1 d . . . . .
H13 H 0.7468 0.2199 0.7593 0.030 Uiso 1 1 calc R . . . .
C7 C 0.31433(10) 0.5875(2) 0.53688(5) 0.0181(2) Uani 1 1 d . . . . .
H7 H 0.3129 0.4969 0.5024 0.022 Uiso 1 1 calc R . . . .
C1 C 0.24272(11) 1.0962(2) 0.44188(6) 0.0222(3) Uani 1 1 d . . . . .
H1A H 0.2121 1.2152 0.4629 0.027 Uiso 1 1 calc R . . . .
H1B H 0.2613 1.1494 0.4049 0.027 Uiso 1 1 calc R . . . .
C19 C -0.10656(11) 0.7181(2) 0.69876(6) 0.0253(3) Uani 1 1 d . . . . .
H19 H -0.1650 0.7221 0.7231 0.030 Uiso 1 1 calc R . . . .
C21 C 0.05407(11) 0.8798(2) 0.66231(5) 0.0219(3) Uani 1 1 d . . . . .
H21 H 0.1062 0.9945 0.6624 0.026 Uiso 1 1 calc R . . . .
C18 C -0.09698(12) 0.5441(2) 0.66360(6) 0.0269(3) Uani 1 1 d . . . . .
H18 H -0.1482 0.4282 0.6644 0.032 Uiso 1 1 calc R . . . .
C15 C 0.54265(11) 0.1891(2) 0.65676(6) 0.0223(3) Uani 1 1 d . . . . .
H15 H 0.5098 0.0952 0.6284 0.027 Uiso 1 1 calc R . . . .
C20 C -0.03110(11) 0.8850(2) 0.69837(6) 0.0250(3) Uani 1 1 d . . . . .
H20 H -0.0372 1.0035 0.7226 0.030 Uiso 1 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
S2 C3 1.8460(14) . ?
S2 C5 1.8391(12) . ?
S1 C3 1.7908(13) . ?
S1 C1 1.8237(13) . ?
O1 C4 1.2165(14) . ?
O3 C9 1.2072(16) . ?
O2 C8 1.2054(16) . ?
N2 C8 1.3973(17) . ?
N2 C10 1.4428(15) . ?
N2 C9 1.3984(16) . ?
N1 C4 1.3548(16) . ?
N1 C2 1.4597(16) . ?
N1 C3 1.4641(15) . ?
C8 C7 1.5135(17) . ?
C11 H11 0.9500 . ?
C11 C10 1.3857(19) . ?
C11 C12 1.3916(18) . ?
C16 C5 1.5081(17) . ?
C16 C17 1.3945(18) . ?
C16 C21 1.3956(18) . ?
C4 C5 1.5705(16) . ?
C6 H6 1.0000 . ?
C6 C5 1.5718(17) . ?
C6 C9 1.5261(16) . ?
C6 C7 1.5542(17) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.5188(18) . ?
C3 C7 1.5378(18) . ?
C10 C15 1.3882(19) . ?
C17 H17 0.9500 . ?
C17 C18 1.3930(19) . ?
C14 H14 0.9500 . ?
C14 C13 1.390(2) . ?
C14 C15 1.3928(18) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(2) . ?
C13 H13 0.9500 . ?
C7 H7 1.0000 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C19 H19 0.9500 . ?
C19 C18 1.389(2) . ?
C19 C20 1.380(2) . ?
C21 H21 0.9500 . ?
C21 C20 1.3947(19) . ?
C18 H18 0.9500 . ?
C15 H15 0.9500 . ?
C20 H20 0.9500 . ?

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
C5 S2 C3 79.76(6) . . ?
C3 S1 C1 91.20(6) . . ?
C8 N2 C10 121.24(10) . . ?
C8 N2 C9 113.38(10) . . ?
C9 N2 C10 125.32(10) . . ?
C4 N1 C2 128.17(10) . . ?
C4 N1 C3 111.92(10) . . ?
C2 N1 C3 115.74(10) . . ?
O2 C8 N2 124.57(12) . . ?
O2 C8 C7 127.58(12) . . ?
N2 C8 C7 107.85(10) . . ?
C10 C11 H11 120.5 . . ?
C10 C11 C12 119.08(13) . . ?
C12 C11 H11 120.5 . . ?
C17 C16 C5 119.62(11) . . ?
C17 C16 C21 119.05(12) . . ?
C21 C16 C5 121.05(12) . . ?
O1 C4 N1 126.83(11) . . ?
O1 C4 C5 126.39(11) . . ?
N1 C4 C5 106.77(10) . . ?
C5 C6 H6 110.6 . . ?
C9 C6 H6 110.6 . . ?
C9 C6 C5 114.40(10) . . ?
C9 C6 C7 104.38(9) . . ?
C7 C6 H6 110.6 . . ?
C7 C6 C5 105.86(10) . . ?
N1 C2 H2A 110.8 . . ?
N1 C2 H2B 110.8 . . ?
N1 C2 C1 104.90(10) . . ?
H2A C2 H2B 108.8 . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
S1 C3 S2 115.04(7) . . ?
N1 C3 S2 103.84(8) . . ?
N1 C3 S1 106.94(8) . . ?
N1 C3 C7 105.82(10) . . ?
C7 C3 S2 102.80(8) . . ?
C7 C3 S1 120.87(9) . . ?
C16 C5 S2 114.96(9) . . ?
C16 C5 C4 112.21(10) . . ?
C16 C5 C6 119.72(10) . . ?
C4 C5 S2 100.71(8) . . ?
C4 C5 C6 104.54(9) . . ?
C6 C5 S2 102.46(8) . . ?
C11 C10 N2 120.08(12) . . ?
C11 C10 C15 121.46(12) . . ?
C15 C10 N2 118.39(11) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.09(13) . . ?
C18 C17 H17 120.0 . . ?
O3 C9 N2 124.68(11) . . ?
O3 C9 C6 127.20(11) . . ?
N2 C9 C6 108.10(10) . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.17(13) . . ?
C15 C14 H14 119.9 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.18(13) . . ?
C13 C12 H12 119.9 . . ?
C14 C13 H13 119.9 . . ?
C12 C13 C14 120.18(12) . . ?
C12 C13 H13 119.9 . . ?
C8 C7 C6 105.37(10) . . ?
C8 C7 C3 114.53(10) . . ?
C8 C7 H7 110.8 . . ?
C6 C7 H7 110.8 . . ?
C3 C7 C6 104.19(10) . . ?
C3 C7 H7 110.8 . . ?
S1 C1 H1A 110.8 . . ?
S1 C1 H1B 110.8 . . ?
C2 C1 S1 104.54(9) . . ?
C2 C1 H1A 110.8 . . ?
C2 C1 H1B 110.8 . . ?
H1A C1 H1B 108.9 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C20 C19 C18 119.95(13) . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.57(13) . . ?
C20 C21 H21 119.7 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.35(13) . . ?
C19 C18 H18 119.8 . . ?
C10 C15 C14 118.92(13) . . ?
C10 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C19 C20 C21 119.97(13) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?

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
S2 C3 C7 C8 -69.47(11) . . . . ?
S2 C3 C7 C6 45.11(10) . . . . ?
S1 C3 C7 C8 60.43(14) . . . . ?
S1 C3 C7 C6 175.01(9) . . . . ?
O1 C4 C5 S2 -137.72(11) . . . . ?
O1 C4 C5 C16 -14.96(17) . . . . ?
O1 C4 C5 C6 116.26(13) . . . . ?
O2 C8 C7 C6 -172.11(14) . . . . ?
O2 C8 C7 C3 -58.22(19) . . . . ?
N2 C8 C7 C6 8.26(14) . . . . ?
N2 C8 C7 C3 122.15(12) . . . . ?
N2 C10 C15 C14 176.61(12) . . . . ?
N1 C4 C5 S2 43.38(11) . . . . ?
N1 C4 C5 C16 166.13(10) . . . . ?
N1 C4 C5 C6 -62.64(12) . . . . ?
N1 C2 C1 S1 40.99(11) . . . . ?
N1 C3 C7 C8 -178.09(10) . . . . ?
N1 C3 C7 C6 -63.51(12) . . . . ?
C8 N2 C10 C11 86.27(16) . . . . ?
C8 N2 C10 C15 -90.70(15) . . . . ?
C8 N2 C9 O3 -173.88(12) . . . . ?
C8 N2 C9 C6 7.76(14) . . . . ?
C11 C10 C15 C14 -0.3(2) . . . . ?
C11 C12 C13 C14 -0.6(2) . . . . ?
C16 C17 C18 C19 0.5(2) . . . . ?
C16 C21 C20 C19 0.55(19) . . . . ?
C4 N1 C2 C1 126.54(13) . . . . ?
C4 N1 C3 S2 -35.11(12) . . . . ?
C4 N1 C3 S1 -157.16(9) . . . . ?
C4 N1 C3 C7 72.76(13) . . . . ?
C2 N1 C4 O1 20.0(2) . . . . ?
C2 N1 C4 C5 -161.07(12) . . . . ?
C2 N1 C3 S2 123.89(10) . . . . ?
C2 N1 C3 S1 1.83(14) . . . . ?
C2 N1 C3 C7 -128.24(11) . . . . ?
C3 S2 C5 C16 -172.58(10) . . . . ?
C3 S2 C5 C4 -51.76(8) . . . . ?
C3 S2 C5 C6 55.91(8) . . . . ?
C3 S1 C1 C2 -35.89(9) . . . . ?
C3 N1 C4 O1 175.78(12) . . . . ?
C3 N1 C4 C5 -5.32(14) . . . . ?
C3 N1 C2 C1 -28.44(14) . . . . ?
C5 S2 C3 S1 167.19(8) . . . . ?
C5 S2 C3 N1 50.68(8) . . . . ?
C5 S2 C3 C7 -59.43(8) . . . . ?
C5 C16 C17 C18 -173.42(12) . . . . ?
C5 C16 C21 C20 172.81(11) . . . . ?
C5 C6 C9 O3 64.49(17) . . . . ?
C5 C6 C9 N2 -117.21(11) . . . . ?
C5 C6 C7 C8 117.34(11) . . . . ?
C5 C6 C7 C3 -3.56(12) . . . . ?
C10 N2 C8 O2 -7.4(2) . . . . ?
C10 N2 C8 C7 172.24(11) . . . . ?
C10 N2 C9 O3 3.5(2) . . . . ?
C10 N2 C9 C6 -174.87(11) . . . . ?
C10 C11 C12 C13 0.4(2) . . . . ?
C17 C16 C5 S2 -175.12(10) . . . . ?
C17 C16 C5 C4 70.59(15) . . . . ?
C17 C16 C5 C6 -52.46(16) . . . . ?
C17 C16 C21 C20 -1.12(19) . . . . ?
C9 N2 C8 O2 170.09(13) . . . . ?
C9 N2 C8 C7 -10.27(15) . . . . ?
C9 N2 C10 C11 -90.91(16) . . . . ?
C9 N2 C10 C15 92.13(15) . . . . ?
C9 C6 C5 S2 75.10(11) . . . . ?
C9 C6 C5 C16 -53.48(14) . . . . ?
C9 C6 C5 C4 179.81(10) . . . . ?
C9 C6 C7 C8 -3.73(13) . . . . ?
C9 C6 C7 C3 -124.64(10) . . . . ?
C12 C11 C10 N2 -176.78(11) . . . . ?
C12 C11 C10 C15 0.09(19) . . . . ?
C13 C14 C15 C10 0.1(2) . . . . ?
C7 C6 C5 S2 -39.25(10) . . . . ?
C7 C6 C5 C16 -167.84(10) . . . . ?
C7 C6 C5 C4 65.46(11) . . . . ?
C7 C6 C9 O3 179.71(12) . . . . ?
C7 C6 C9 N2 -1.99(13) . . . . ?
C1 S1 C3 S2 -94.60(8) . . . . ?
C1 S1 C3 N1 20.13(10) . . . . ?
C1 S1 C3 C7 141.06(11) . . . . ?
C21 C16 C5 S2 10.99(15) . . . . ?
C21 C16 C5 C4 -103.31(13) . . . . ?
C21 C16 C5 C6 133.65(12) . . . . ?
C21 C16 C17 C18 0.60(19) . . . . ?
C18 C19 C20 C21 0.6(2) . . . . ?
C15 C14 C13 C12 0.4(2) . . . . ?
C20 C19 C18 C17 -1.1(2) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perflourotether oil'
####################################################################### 
# 
# 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_2014acc0001
_database_code_depnum_ccdc_archive 'CCDC 1830926'
_audit_update_record             
;
2018-03-19 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
#VD-1

_audit_creation_date             2014-04-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C21 H16 N2 O3 S2'
_chemical_formula_sum            'C21 H16 N2 O3 S2'
_chemical_formula_weight         408.50
_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 0.0033 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'
N N 0.0061 0.0033 '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'

_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                   11.0765(11)
_cell_length_b                   18.7037(19)
_cell_length_c                   17.8788(18)
_cell_angle_alpha                90
_cell_angle_beta                 91.808(2)
_cell_angle_gamma                90
_cell_volume                     3702.1(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9635
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.3
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.314
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1696
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            33998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.522
_diffrn_reflns_theta_min         2.279
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       XPlain
_diffrn_orient_matrix_UB_11      -0.088048
_diffrn_orient_matrix_UB_12      0.013858
_diffrn_orient_matrix_UB_13      -0.014643
_diffrn_orient_matrix_UB_21      0.011712
_diffrn_orient_matrix_UB_22      0.042606
_diffrn_orient_matrix_UB_23      -0.030101
_diffrn_orient_matrix_UB_31      0.000673
_diffrn_orient_matrix_UB_32      -0.032411
_diffrn_orient_matrix_UB_33      -0.045614
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7402
_reflns_number_total             8515
_reflns_shell_number_unique_all  8787
_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       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_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    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.821
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         8515
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0315
_refine_ls_restrained_S_all      1.049
_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)+(0.0404P)²+1.2548P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0829
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C106(H106), C107(H107), C206(H206), C207(H207)
2.b Secondary CH2 refined with riding coordinates:
 C101(H10A,H10B), C102(H10C,H10D), C201(H20A,H20B), C202(H20C,H20D)
2.c Aromatic/amide H refined with riding coordinates:
 C111(H111), C112(H112), C113(H113), C114(H114), C115(H115), C117(H117),
 C118(H118), C119(H119), C120(H120), C121(H121), C211(H211), C212(H212),
 C213(H213), C214(H214), C215(H215), C217(H217), C218(H218), C219(H219),
 C220(H220), C221(H221)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
S101 S 0.11389(3) 0.40609(2) 0.71424(2) 0.01606(8) Uani 1 1 d . . . . .
S102 S 0.36816(3) 0.44824(2) 0.78279(2) 0.01494(8) Uani 1 1 d . . . . .
O101 O 0.43589(9) 0.25657(5) 0.82060(5) 0.0183(2) Uani 1 1 d . . . . .
O102 O 0.21573(9) 0.32678(6) 0.56146(6) 0.0226(2) Uani 1 1 d . . . . .
O103 O 0.58813(9) 0.26287(6) 0.65830(6) 0.0203(2) Uani 1 1 d . . . . .
N101 N 0.28880(10) 0.31936(6) 0.75539(6) 0.0141(2) Uani 1 1 d . . . . .
N102 N 0.40032(10) 0.27948(6) 0.60065(6) 0.0157(2) Uani 1 1 d . . . . .
C101 C 0.08125(13) 0.33334(8) 0.77896(8) 0.0194(3) Uani 1 1 d . . . . .
H10A H 0.0837 0.3507 0.8313 0.023 Uiso 1 1 calc R . . . .
H10B H 0.0004 0.3128 0.7674 0.023 Uiso 1 1 calc R . . . .
C102 C 0.17937(12) 0.27808(8) 0.76742(8) 0.0180(3) Uani 1 1 d . . . . .
H10C H 0.1897 0.2471 0.8121 0.022 Uiso 1 1 calc R . . . .
H10D H 0.1592 0.2477 0.7234 0.022 Uiso 1 1 calc R . . . .
C103 C 0.27371(12) 0.39031(7) 0.72151(7) 0.0135(3) Uani 1 1 d . . . . .
C104 C 0.40119(12) 0.30911(7) 0.78610(7) 0.0136(3) Uani 1 1 d . . . . .
C105 C 0.47704(12) 0.37520(7) 0.76428(7) 0.0136(3) Uani 1 1 d . . . . .
C106 C 0.47732(12) 0.37442(7) 0.67627(7) 0.0145(3) Uani 1 1 d . . . . .
H106 H 0.5361 0.4100 0.6570 0.017 Uiso 1 1 calc R . . . .
C107 C 0.34753(12) 0.39188(7) 0.64869(7) 0.0140(3) Uani 1 1 d . . . . .
H107 H 0.3423 0.4394 0.6231 0.017 Uiso 1 1 calc R . . . .
C108 C 0.30991(12) 0.33136(8) 0.59708(7) 0.0159(3) Uani 1 1 d . . . . .
C109 C 0.50125(12) 0.29995(8) 0.64523(7) 0.0153(3) Uani 1 1 d . . . . .
C110 C 0.38166(12) 0.20927(8) 0.57023(8) 0.0173(3) Uani 1 1 d . . . . .
C111 C 0.40246(15) 0.14988(9) 0.61527(9) 0.0258(3) Uani 1 1 d . . . . .
H111 H 0.4351 0.1553 0.6647 0.031 Uiso 1 1 calc R . . . .
C112 C 0.37489(16) 0.08228(9) 0.58713(10) 0.0309(4) Uani 1 1 d . . . . .
H112 H 0.3896 0.0412 0.6173 0.037 Uiso 1 1 calc R . . . .
C113 C 0.32594(16) 0.07462(9) 0.51511(9) 0.0296(4) Uani 1 1 d . . . . .
H113 H 0.3068 0.0284 0.4962 0.036 Uiso 1 1 calc R . . . .
C114 C 0.30510(14) 0.13440(9) 0.47099(8) 0.0255(3) Uani 1 1 d . . . . .
H114 H 0.2703 0.1290 0.4221 0.031 Uiso 1 1 calc R . . . .
C115 C 0.33451(13) 0.20222(8) 0.49751(8) 0.0201(3) Uani 1 1 d . . . . .
H115 H 0.3227 0.2431 0.4666 0.024 Uiso 1 1 calc R . . . .
C116 C 0.59367(12) 0.38416(7) 0.80840(7) 0.0147(3) Uani 1 1 d . . . . .
C117 C 0.58994(13) 0.38221(8) 0.88664(8) 0.0189(3) Uani 1 1 d . . . . .
H117 H 0.5153 0.3740 0.9099 0.023 Uiso 1 1 calc R . . . .
C118 C 0.69380(14) 0.39215(8) 0.93040(8) 0.0228(3) Uani 1 1 d . . . . .
H118 H 0.6903 0.3900 0.9834 0.027 Uiso 1 1 calc R . . . .
C119 C 0.80294(14) 0.40530(8) 0.89708(9) 0.0249(3) Uani 1 1 d . . . . .
H119 H 0.8744 0.4122 0.9270 0.030 Uiso 1 1 calc R . . . .
C120 C 0.80686(14) 0.40829(8) 0.81966(9) 0.0247(3) Uani 1 1 d . . . . .
H120 H 0.8812 0.4183 0.7967 0.030 Uiso 1 1 calc R . . . .
C121 C 0.70331(13) 0.39680(8) 0.77512(8) 0.0197(3) Uani 1 1 d . . . . .
H121 H 0.7076 0.3976 0.7221 0.024 Uiso 1 1 calc R . . . .
S201 S 0.09562(3) 0.65555(2) 0.69084(2) 0.02105(9) Uani 1 1 d . . . . .
S202 S 0.14690(3) 0.53427(2) 0.57728(2) 0.01645(8) Uani 1 1 d . . . . .
O201 O 0.37813(9) 0.64181(6) 0.48705(6) 0.0215(2) Uani 1 1 d . . . . .
O202 O -0.03532(10) 0.77072(5) 0.56069(5) 0.0207(2) Uani 1 1 d . . . . .
O203 O 0.12988(9) 0.67634(5) 0.35048(5) 0.0174(2) Uani 1 1 d . . . . .
N201 N 0.22970(10) 0.66471(6) 0.57207(6) 0.0156(2) Uani 1 1 d . . . . .
N202 N 0.05081(10) 0.73920(6) 0.44895(6) 0.0146(2) Uani 1 1 d . . . . .
C201 C 0.25525(15) 0.67785(9) 0.70378(8) 0.0270(3) Uani 1 1 d . . . . .
H20A H 0.2674 0.7134 0.7444 0.032 Uiso 1 1 calc R . . . .
H20B H 0.3034 0.6346 0.7163 0.032 Uiso 1 1 calc R . . . .
C202 C 0.29142(14) 0.70889(8) 0.62886(8) 0.0230(3) Uani 1 1 d . . . . .
H20C H 0.2655 0.7594 0.6242 0.028 Uiso 1 1 calc R . . . .
H20D H 0.3801 0.7065 0.6237 0.028 Uiso 1 1 calc R . . . .
C203 C 0.11783(12) 0.63049(7) 0.59556(7) 0.0158(3) Uani 1 1 d . . . . .
C204 C 0.28021(12) 0.62993(7) 0.51330(7) 0.0163(3) Uani 1 1 d . . . . .
C205 C 0.18662(12) 0.57291(7) 0.48567(7) 0.0148(3) Uani 1 1 d . . . . .
C206 C 0.06748(12) 0.61411(7) 0.46341(7) 0.0138(3) Uani 1 1 d . . . . .
H206 H 0.0070 0.5807 0.4398 0.017 Uiso 1 1 calc R . . . .
C207 C 0.01805(12) 0.64636(7) 0.53557(7) 0.0142(3) Uani 1 1 d . . . . .
H207 H -0.0607 0.6242 0.5486 0.017 Uiso 1 1 calc R . . . .
C208 C 0.00485(12) 0.72584(7) 0.51999(7) 0.0152(3) Uani 1 1 d . . . . .
C209 C 0.08829(12) 0.67769(7) 0.41236(7) 0.0140(3) Uani 1 1 d . . . . .
C210 C 0.06196(13) 0.81002(7) 0.41913(7) 0.0160(3) Uani 1 1 d . . . . .
C211 C 0.17471(13) 0.83399(8) 0.39789(7) 0.0179(3) Uani 1 1 d . . . . .
H211 H 0.2430 0.8033 0.4005 0.022 Uiso 1 1 calc R . . . .
C212 C 0.18514(15) 0.90400(8) 0.37271(8) 0.0238(3) Uani 1 1 d . . . . .
H212 H 0.2614 0.9214 0.3580 0.029 Uiso 1 1 calc R . . . .
C213 C 0.08540(17) 0.94866(8) 0.36893(9) 0.0295(4) Uani 1 1 d . . . . .
H213 H 0.0938 0.9967 0.3525 0.035 Uiso 1 1 calc R . . . .
C214 C -0.02674(17) 0.92343(9) 0.38905(9) 0.0298(4) Uani 1 1 d . . . . .
H214 H -0.0952 0.9540 0.3857 0.036 Uiso 1 1 calc R . . . .
C215 C -0.03920(14) 0.85350(8) 0.41405(8) 0.0227(3) Uani 1 1 d . . . . .
H215 H -0.1160 0.8358 0.4274 0.027 Uiso 1 1 calc R . . . .
C216 C 0.23321(13) 0.51746(7) 0.43257(8) 0.0167(3) Uani 1 1 d . . . . .
C217 C 0.33984(14) 0.48112(8) 0.45204(8) 0.0219(3) Uani 1 1 d . . . . .
H217 H 0.3840 0.4940 0.4964 0.026 Uiso 1 1 calc R . . . .
C218 C 0.38216(15) 0.42642(9) 0.40741(9) 0.0277(3) Uani 1 1 d . . . . .
H218 H 0.4545 0.4020 0.4216 0.033 Uiso 1 1 calc R . . . .
C219 C 0.31899(16) 0.40733(8) 0.34202(9) 0.0278(3) Uani 1 1 d . . . . .
H219 H 0.3478 0.3698 0.3115 0.033 Uiso 1 1 calc R . . . .
C220 C 0.21352(15) 0.44350(8) 0.32168(9) 0.0242(3) Uani 1 1 d . . . . .
H220 H 0.1702 0.4309 0.2769 0.029 Uiso 1 1 calc R . . . .
C221 C 0.17099(13) 0.49827(8) 0.36680(8) 0.0195(3) Uani 1 1 d . . . . .
H221 H 0.0987 0.5227 0.3525 0.023 Uiso 1 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
S101 C101 1.8295(14) . ?
S101 C103 1.7953(14) . ?
S102 C103 1.8429(14) . ?
S102 C105 1.8589(14) . ?
O101 C104 1.2163(16) . ?
O102 C108 1.2079(17) . ?
O103 C109 1.2032(17) . ?
N101 C102 1.4588(17) . ?
N101 C103 1.4662(17) . ?
N101 C104 1.3581(17) . ?
N102 C108 1.3945(18) . ?
N102 C109 1.4055(17) . ?
N102 C110 1.4337(18) . ?
C101 H10A 0.9900 . ?
C101 H10B 0.9900 . ?
C101 C102 1.519(2) . ?
C102 H10C 0.9900 . ?
C102 H10D 0.9900 . ?
C103 C107 1.5593(17) . ?
C104 C105 1.5512(18) . ?
C105 C106 1.5737(17) . ?
C105 C116 1.5017(18) . ?
C106 H106 1.0000 . ?
C106 C107 1.5400(18) . ?
C106 C109 1.5257(19) . ?
C107 H107 1.0000 . ?
C107 C108 1.5106(19) . ?
C110 C111 1.387(2) . ?
C110 C115 1.3920(19) . ?
C111 H111 0.9500 . ?
C111 C112 1.391(2) . ?
C112 H112 0.9500 . ?
C112 C113 1.389(2) . ?
C113 H113 0.9500 . ?
C113 C114 1.383(2) . ?
C114 H114 0.9500 . ?
C114 C115 1.389(2) . ?
C115 H115 0.9500 . ?
C116 C117 1.4012(18) . ?
C116 C121 1.389(2) . ?
C117 H117 0.9500 . ?
C117 C118 1.383(2) . ?
C118 H118 0.9500 . ?
C118 C119 1.386(2) . ?
C119 H119 0.9500 . ?
C119 C120 1.387(2) . ?
C120 H120 0.9500 . ?
C120 C121 1.392(2) . ?
C121 H121 0.9500 . ?
S201 C201 1.8242(17) . ?
S201 C203 1.7913(14) . ?
S202 C203 1.8590(15) . ?
S202 C205 1.8558(14) . ?
O201 C204 1.2159(17) . ?
O202 C208 1.2051(17) . ?
O203 C209 1.2120(16) . ?
N201 C202 1.4618(17) . ?
N201 C203 1.4678(18) . ?
N201 C204 1.3702(18) . ?
N202 C208 1.4055(16) . ?
N202 C209 1.3932(17) . ?
N202 C210 1.4346(17) . ?
C201 H20A 0.9900 . ?
C201 H20B 0.9900 . ?
C201 C202 1.525(2) . ?
C202 H20C 0.9900 . ?
C202 H20D 0.9900 . ?
C203 C207 1.5444(18) . ?
C204 C205 1.5567(19) . ?
C205 C206 1.5686(18) . ?
C205 C216 1.5080(19) . ?
C206 H206 1.0000 . ?
C206 C207 1.5402(18) . ?
C206 C209 1.5211(18) . ?
C207 H207 1.0000 . ?
C207 C208 1.5187(19) . ?
C210 C211 1.391(2) . ?
C210 C215 1.385(2) . ?
C211 H211 0.9500 . ?
C211 C212 1.391(2) . ?
C212 H212 0.9500 . ?
C212 C213 1.385(2) . ?
C213 H213 0.9500 . ?
C213 C214 1.387(3) . ?
C214 H214 0.9500 . ?
C214 C215 1.391(2) . ?
C215 H215 0.9500 . ?
C216 C217 1.397(2) . ?
C216 C221 1.391(2) . ?
C217 H217 0.9500 . ?
C217 C218 1.388(2) . ?
C218 H218 0.9500 . ?
C218 C219 1.390(2) . ?
C219 H219 0.9500 . ?
C219 C220 1.388(2) . ?
C220 H220 0.9500 . ?
C220 C221 1.395(2) . ?
C221 H221 0.9500 . ?

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
C103 S101 C101 92.64(6) . . ?
C103 S102 C105 79.71(6) . . ?
C102 N101 C103 117.10(11) . . ?
C104 N101 C102 128.39(11) . . ?
C104 N101 C103 112.69(11) . . ?
C108 N102 C109 113.18(11) . . ?
C108 N102 C110 121.69(11) . . ?
C109 N102 C110 124.55(12) . . ?
S101 C101 H10A 110.7 . . ?
S101 C101 H10B 110.7 . . ?
H10A C101 H10B 108.8 . . ?
C102 C101 S101 105.29(9) . . ?
C102 C101 H10A 110.7 . . ?
C102 C101 H10B 110.7 . . ?
N101 C102 C101 105.15(11) . . ?
N101 C102 H10C 110.7 . . ?
N101 C102 H10D 110.7 . . ?
C101 C102 H10C 110.7 . . ?
C101 C102 H10D 110.7 . . ?
H10C C102 H10D 108.8 . . ?
S101 C103 S102 119.10(7) . . ?
N101 C103 S101 106.14(9) . . ?
N101 C103 S102 103.38(8) . . ?
N101 C103 C107 107.82(10) . . ?
C107 C103 S101 118.57(9) . . ?
C107 C103 S102 100.51(9) . . ?
O101 C104 N101 126.16(12) . . ?
O101 C104 C105 127.33(12) . . ?
N101 C104 C105 106.42(11) . . ?
C104 C105 S102 100.45(8) . . ?
C104 C105 C106 105.20(10) . . ?
C106 C105 S102 101.92(8) . . ?
C116 C105 S102 112.13(9) . . ?
C116 C105 C104 114.88(11) . . ?
C116 C105 C106 119.83(11) . . ?
C105 C106 H106 111.1 . . ?
C107 C106 C105 106.67(10) . . ?
C107 C106 H106 111.1 . . ?
C109 C106 C105 112.21(11) . . ?
C109 C106 H106 111.1 . . ?
C109 C106 C107 104.37(11) . . ?
C103 C107 H107 112.0 . . ?
C106 C107 C103 103.74(10) . . ?
C106 C107 H107 112.0 . . ?
C108 C107 C103 110.74(11) . . ?
C108 C107 C106 105.87(11) . . ?
C108 C107 H107 112.0 . . ?
O102 C108 N102 125.57(13) . . ?
O102 C108 C107 126.31(13) . . ?
N102 C108 C107 108.03(11) . . ?
O103 C109 N102 124.76(13) . . ?
O103 C109 C106 127.07(12) . . ?
N102 C109 C106 108.11(11) . . ?
C111 C110 N102 119.60(12) . . ?
C111 C110 C115 121.13(14) . . ?
C115 C110 N102 119.10(13) . . ?
C110 C111 H111 120.4 . . ?
C110 C111 C112 119.17(14) . . ?
C112 C111 H111 120.4 . . ?
C111 C112 H112 119.9 . . ?
C113 C112 C111 120.26(16) . . ?
C113 C112 H112 119.9 . . ?
C112 C113 H113 120.0 . . ?
C114 C113 C112 119.91(15) . . ?
C114 C113 H113 120.0 . . ?
C113 C114 H114 119.7 . . ?
C113 C114 C115 120.67(14) . . ?
C115 C114 H114 119.7 . . ?
C110 C115 H115 120.6 . . ?
C114 C115 C110 118.83(14) . . ?
C114 C115 H115 120.6 . . ?
C117 C116 C105 118.00(12) . . ?
C121 C116 C105 122.89(12) . . ?
C121 C116 C117 119.06(13) . . ?
C116 C117 H117 119.6 . . ?
C118 C117 C116 120.73(14) . . ?
C118 C117 H117 119.6 . . ?
C117 C118 H118 119.9 . . ?
C117 C118 C119 120.11(14) . . ?
C119 C118 H118 119.9 . . ?
C118 C119 H119 120.3 . . ?
C118 C119 C120 119.41(14) . . ?
C120 C119 H119 120.3 . . ?
C119 C120 H120 119.6 . . ?
C119 C120 C121 120.89(14) . . ?
C121 C120 H120 119.6 . . ?
C116 C121 C120 119.78(14) . . ?
C116 C121 H121 120.1 . . ?
C120 C121 H121 120.1 . . ?
C203 S201 C201 91.08(7) . . ?
C205 S202 C203 79.94(6) . . ?
C202 N201 C203 115.36(11) . . ?
C204 N201 C202 127.42(12) . . ?
C204 N201 C203 112.40(11) . . ?
C208 N202 C210 122.53(11) . . ?
C209 N202 C208 113.54(11) . . ?
C209 N202 C210 123.89(11) . . ?
S201 C201 H20A 110.8 . . ?
S201 C201 H20B 110.8 . . ?
H20A C201 H20B 108.9 . . ?
C202 C201 S201 104.84(10) . . ?
C202 C201 H20A 110.8 . . ?
C202 C201 H20B 110.8 . . ?
N201 C202 C201 105.36(12) . . ?
N201 C202 H20C 110.7 . . ?
N201 C202 H20D 110.7 . . ?
C201 C202 H20C 110.7 . . ?
C201 C202 H20D 110.7 . . ?
H20C C202 H20D 108.8 . . ?
S201 C203 S202 116.76(7) . . ?
N201 C203 S201 107.49(9) . . ?
N201 C203 S202 102.67(9) . . ?
N201 C203 C207 108.04(11) . . ?
C207 C203 S201 119.57(10) . . ?
C207 C203 S202 100.84(9) . . ?
O201 C204 N201 126.87(13) . . ?
O201 C204 C205 126.58(13) . . ?
N201 C204 C205 106.55(11) . . ?
C204 C205 S202 99.25(8) . . ?
C204 C205 C206 106.89(11) . . ?
C206 C205 S202 101.20(9) . . ?
C216 C205 S202 112.53(9) . . ?
C216 C205 C204 115.67(11) . . ?
C216 C205 C206 118.69(11) . . ?
C205 C206 H206 110.3 . . ?
C207 C206 C205 107.36(10) . . ?
C207 C206 H206 110.3 . . ?
C209 C206 C205 113.20(11) . . ?
C209 C206 H206 110.3 . . ?
C209 C206 C207 105.13(11) . . ?
C203 C207 H207 111.6 . . ?
C206 C207 C203 103.94(11) . . ?
C206 C207 H207 111.6 . . ?
C208 C207 C203 112.22(11) . . ?
C208 C207 C206 105.33(10) . . ?
C208 C207 H207 111.6 . . ?
O202 C208 N202 124.96(13) . . ?
O202 C208 C207 127.32(12) . . ?
N202 C208 C207 107.71(11) . . ?
O203 C209 N202 124.98(13) . . ?
O203 C209 C206 126.91(12) . . ?
N202 C209 C206 108.11(11) . . ?
C211 C210 N202 119.19(13) . . ?
C215 C210 N202 119.17(13) . . ?
C215 C210 C211 121.61(13) . . ?
C210 C211 H211 120.8 . . ?
C212 C211 C210 118.45(14) . . ?
C212 C211 H211 120.8 . . ?
C211 C212 H212 119.7 . . ?
C213 C212 C211 120.63(15) . . ?
C213 C212 H212 119.7 . . ?
C212 C213 H213 119.9 . . ?
C212 C213 C214 120.11(15) . . ?
C214 C213 H213 119.9 . . ?
C213 C214 H214 119.9 . . ?
C213 C214 C215 120.15(15) . . ?
C215 C214 H214 119.9 . . ?
C210 C215 C214 119.02(15) . . ?
C210 C215 H215 120.5 . . ?
C214 C215 H215 120.5 . . ?
C217 C216 C205 118.76(13) . . ?
C221 C216 C205 122.64(12) . . ?
C221 C216 C217 118.51(13) . . ?
C216 C217 H217 119.6 . . ?
C218 C217 C216 120.90(14) . . ?
C218 C217 H217 119.6 . . ?
C217 C218 H218 119.9 . . ?
C217 C218 C219 120.18(15) . . ?
C219 C218 H218 119.9 . . ?
C218 C219 H219 120.3 . . ?
C220 C219 C218 119.48(14) . . ?
C220 C219 H219 120.3 . . ?
C219 C220 H220 119.9 . . ?
C219 C220 C221 120.20(14) . . ?
C221 C220 H220 119.9 . . ?
C216 C221 C220 120.73(14) . . ?
C216 C221 H221 119.6 . . ?
C220 C221 H221 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
S101 C101 C102 N101 37.62(12) . . . . ?
S101 C103 C107 C106 -178.51(9) . . . . ?
S101 C103 C107 C108 -65.33(13) . . . . ?
S102 C103 C107 C106 49.86(11) . . . . ?
S102 C103 C107 C108 163.04(9) . . . . ?
S102 C105 C106 C107 -35.57(11) . . . . ?
S102 C105 C106 C109 -149.28(9) . . . . ?
S102 C105 C116 C117 62.70(14) . . . . ?
S102 C105 C116 C121 -114.88(13) . . . . ?
O101 C104 C105 S102 -139.00(12) . . . . ?
O101 C104 C105 C106 115.48(14) . . . . ?
O101 C104 C105 C116 -18.48(19) . . . . ?
N101 C103 C107 C106 -58.01(13) . . . . ?
N101 C103 C107 C108 55.17(13) . . . . ?
N101 C104 C105 S102 44.35(11) . . . . ?
N101 C104 C105 C106 -61.18(13) . . . . ?
N101 C104 C105 C116 164.86(11) . . . . ?
N102 C110 C111 C112 174.88(14) . . . . ?
N102 C110 C115 C114 -173.51(13) . . . . ?
C101 S101 C103 S102 -100.48(8) . . . . ?
C101 S101 C103 N101 15.42(9) . . . . ?
C101 S101 C103 C107 136.77(11) . . . . ?
C102 N101 C103 S101 5.66(13) . . . . ?
C102 N101 C103 S102 131.76(10) . . . . ?
C102 N101 C103 C107 -122.36(12) . . . . ?
C102 N101 C104 O101 12.4(2) . . . . ?
C102 N101 C104 C105 -170.88(12) . . . . ?
C103 S101 C101 C102 -31.40(10) . . . . ?
C103 S102 C105 C104 -52.55(8) . . . . ?
C103 S102 C105 C106 55.60(8) . . . . ?
C103 S102 C105 C116 -175.01(10) . . . . ?
C103 N101 C102 C101 -28.97(15) . . . . ?
C103 N101 C104 O101 176.41(12) . . . . ?
C103 N101 C104 C105 -6.88(14) . . . . ?
C103 C107 C108 O102 71.61(17) . . . . ?
C103 C107 C108 N102 -105.24(12) . . . . ?
C104 N101 C102 C101 134.43(14) . . . . ?
C104 N101 C103 S101 -160.29(9) . . . . ?
C104 N101 C103 S102 -34.19(12) . . . . ?
C104 N101 C103 C107 71.69(13) . . . . ?
C104 C105 C106 C107 68.87(13) . . . . ?
C104 C105 C106 C109 -44.84(14) . . . . ?
C104 C105 C116 C117 -51.14(16) . . . . ?
C104 C105 C116 C121 131.27(14) . . . . ?
C105 S102 C103 S101 167.25(9) . . . . ?
C105 S102 C103 N101 49.90(8) . . . . ?
C105 S102 C103 C107 -61.44(8) . . . . ?
C105 C106 C107 C103 -8.47(13) . . . . ?
C105 C106 C107 C108 -125.12(11) . . . . ?
C105 C106 C109 O103 -58.15(18) . . . . ?
C105 C106 C109 N102 118.91(12) . . . . ?
C105 C116 C117 C118 -178.16(13) . . . . ?
C105 C116 C121 C120 176.65(13) . . . . ?
C106 C105 C116 C117 -177.94(12) . . . . ?
C106 C105 C116 C121 4.5(2) . . . . ?
C106 C107 C108 O102 -176.57(13) . . . . ?
C106 C107 C108 N102 6.58(14) . . . . ?
C107 C106 C109 O103 -173.27(13) . . . . ?
C107 C106 C109 N102 3.79(13) . . . . ?
C108 N102 C109 O103 177.46(13) . . . . ?
C108 N102 C109 C106 0.31(15) . . . . ?
C108 N102 C110 C111 -125.57(15) . . . . ?
C108 N102 C110 C115 49.78(18) . . . . ?
C109 N102 C108 O102 178.69(13) . . . . ?
C109 N102 C108 C107 -4.43(15) . . . . ?
C109 N102 C110 C111 45.07(19) . . . . ?
C109 N102 C110 C115 -139.58(13) . . . . ?
C109 C106 C107 C103 110.48(11) . . . . ?
C109 C106 C107 C108 -6.17(13) . . . . ?
C110 N102 C108 O102 -9.7(2) . . . . ?
C110 N102 C108 C107 167.19(11) . . . . ?
C110 N102 C109 O103 6.1(2) . . . . ?
C110 N102 C109 C106 -171.03(11) . . . . ?
C110 C111 C112 C113 -0.7(3) . . . . ?
C111 C110 C115 C114 1.8(2) . . . . ?
C111 C112 C113 C114 0.4(3) . . . . ?
C112 C113 C114 C115 1.1(2) . . . . ?
C113 C114 C115 C110 -2.1(2) . . . . ?
C115 C110 C111 C112 -0.4(2) . . . . ?
C116 C105 C106 C107 -159.96(12) . . . . ?
C116 C105 C106 C109 86.32(15) . . . . ?
C116 C117 C118 C119 1.0(2) . . . . ?
C117 C116 C121 C120 -0.9(2) . . . . ?
C117 C118 C119 C120 -0.1(2) . . . . ?
C118 C119 C120 C121 -1.4(2) . . . . ?
C119 C120 C121 C116 1.9(2) . . . . ?
C121 C116 C117 C118 -0.5(2) . . . . ?
S201 C201 C202 N201 -39.88(14) . . . . ?
S201 C203 C207 C206 -177.31(9) . . . . ?
S201 C203 C207 C208 69.38(14) . . . . ?
S202 C203 C207 C206 -47.84(11) . . . . ?
S202 C203 C207 C208 -161.15(9) . . . . ?
S202 C205 C206 C207 37.27(11) . . . . ?
S202 C205 C206 C209 152.84(9) . . . . ?
S202 C205 C216 C217 -62.68(15) . . . . ?
S202 C205 C216 C221 113.80(13) . . . . ?
O201 C204 C205 S202 134.48(13) . . . . ?
O201 C204 C205 C206 -120.74(14) . . . . ?
O201 C204 C205 C216 13.89(19) . . . . ?
N201 C203 C207 C206 59.45(13) . . . . ?
N201 C203 C207 C208 -53.86(14) . . . . ?
N201 C204 C205 S202 -46.48(11) . . . . ?
N201 C204 C205 C206 58.30(13) . . . . ?
N201 C204 C205 C216 -167.07(11) . . . . ?
N202 C210 C211 C212 -176.75(12) . . . . ?
N202 C210 C215 C214 176.45(13) . . . . ?
C201 S201 C203 S202 94.02(9) . . . . ?
C201 S201 C203 N201 -20.58(10) . . . . ?
C201 S201 C203 C207 -144.09(12) . . . . ?
C202 N201 C203 S201 -0.51(14) . . . . ?
C202 N201 C203 S202 -124.20(11) . . . . ?
C202 N201 C203 C207 129.79(12) . . . . ?
C202 N201 C204 O201 -18.3(2) . . . . ?
C202 N201 C204 C205 162.65(13) . . . . ?
C203 S201 C201 C202 35.34(12) . . . . ?
C203 S202 C205 C204 53.83(9) . . . . ?
C203 S202 C205 C206 -55.58(9) . . . . ?
C203 S202 C205 C216 176.70(11) . . . . ?
C203 N201 C202 C201 26.73(17) . . . . ?
C203 N201 C204 O201 -172.31(13) . . . . ?
C203 N201 C204 C205 8.65(14) . . . . ?
C203 C207 C208 O202 -70.56(18) . . . . ?
C203 C207 C208 N202 108.18(12) . . . . ?
C204 N201 C202 C201 -126.62(15) . . . . ?
C204 N201 C203 S201 156.82(9) . . . . ?
C204 N201 C203 S202 33.14(12) . . . . ?
C204 N201 C203 C207 -72.88(14) . . . . ?
C204 C205 C206 C207 -66.10(13) . . . . ?
C204 C205 C206 C209 49.47(14) . . . . ?
C204 C205 C216 C217 50.42(17) . . . . ?
C204 C205 C216 C221 -133.10(14) . . . . ?
C205 S202 C203 S201 -167.87(9) . . . . ?
C205 S202 C203 N201 -50.60(8) . . . . ?
C205 S202 C203 C207 60.88(9) . . . . ?
C205 C206 C207 C203 6.52(14) . . . . ?
C205 C206 C207 C208 124.68(11) . . . . ?
C205 C206 C209 O203 61.00(17) . . . . ?
C205 C206 C209 N202 -119.10(12) . . . . ?
C205 C216 C217 C218 175.79(14) . . . . ?
C205 C216 C221 C220 -175.90(13) . . . . ?
C206 C205 C216 C217 179.50(13) . . . . ?
C206 C205 C216 C221 -4.01(19) . . . . ?
C206 C207 C208 O202 176.99(13) . . . . ?
C206 C207 C208 N202 -4.27(14) . . . . ?
C207 C206 C209 O203 177.88(13) . . . . ?
C207 C206 C209 N202 -2.22(14) . . . . ?
C208 N202 C209 O203 179.39(12) . . . . ?
C208 N202 C209 C206 -0.52(15) . . . . ?
C208 N202 C210 C211 122.51(14) . . . . ?
C208 N202 C210 C215 -55.80(18) . . . . ?
C209 N202 C208 O202 -178.12(13) . . . . ?
C209 N202 C208 C207 3.10(15) . . . . ?
C209 N202 C210 C211 -54.84(18) . . . . ?
C209 N202 C210 C215 126.84(14) . . . . ?
C209 C206 C207 C203 -114.29(11) . . . . ?
C209 C206 C207 C208 3.88(13) . . . . ?
C210 N202 C208 O202 4.3(2) . . . . ?
C210 N202 C208 C207 -174.50(12) . . . . ?
C210 N202 C209 O203 -3.0(2) . . . . ?
C210 N202 C209 C206 177.05(12) . . . . ?
C210 C211 C212 C213 0.0(2) . . . . ?
C211 C210 C215 C214 -1.8(2) . . . . ?
C211 C212 C213 C214 -1.2(2) . . . . ?
C212 C213 C214 C215 0.9(2) . . . . ?
C213 C214 C215 C210 0.6(2) . . . . ?
C215 C210 C211 C212 1.5(2) . . . . ?
C216 C205 C206 C207 160.88(11) . . . . ?
C216 C205 C206 C209 -83.55(15) . . . . ?
C216 C217 C218 C219 0.5(2) . . . . ?
C217 C216 C221 C220 0.6(2) . . . . ?
C217 C218 C219 C220 0.1(3) . . . . ?
C218 C219 C220 C221 -0.4(2) . . . . ?
C219 C220 C221 C216 0.0(2) . . . . ?
C221 C216 C217 C218 -0.8(2) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perflourotether oil'
