# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_ll_170506
_database_code_depnum_ccdc_archive 'CCDC 1831051'
_audit_update_record             
;
2018-03-20 deposited with the CCDC.
2019-02-01 downloaded from the CCDC.
;
_audit_creation_date             2017-05-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H19 N O4 S'
_chemical_formula_sum            'C21 H19 N O4 S'
_chemical_formula_weight         381.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.07481(16)
_cell_length_b                   15.0220(2)
_cell_length_c                   12.7620(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.1959(16)
_cell_angle_gamma                90
_cell_volume                     1717.38(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6687
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.8990
_cell_measurement_theta_min      4.5640
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.924
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56671
_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_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10760
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         4.581
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4741
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   11.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5672   57.0000  -30.0000 43

#__ type_ start__ end____ width___ exp.time_
  2 omega   33.00   86.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -30.0000 -150.0000 53

#__ type_ start__ end____ width___ exp.time_
  3 omega   46.00   88.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -45.0000 -180.0000 42

#__ type_ start__ end____ width___ exp.time_
  4 omega   60.00  107.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -94.0000 -150.0000 47

#__ type_ start__ end____ width___ exp.time_
  5 omega   54.00   89.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -30.0000  -60.0000 35

#__ type_ start__ end____ width___ exp.time_
  6 omega   49.00  108.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -94.0000  -60.0000 59

#__ type_ start__ end____ width___ exp.time_
  7 omega   50.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -94.0000   30.0000 42

#__ type_ start__ end____ width___ exp.time_
  8 omega   40.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -45.0000    0.0000 58

#__ type_ start__ end____ width___ exp.time_
  9 omega   79.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.8067   30.0000  -30.0000 99

#__ type_ start__ end____ width___ exp.time_
 10 omega  127.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.8067   61.0000  -90.0000 49

#__ type_ start__ end____ width___ exp.time_
 11 omega   85.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.8067   45.0000 -120.0000 93

#__ type_ start__ end____ width___ exp.time_
 12 omega   44.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5672 -125.0000 -180.0000 52

#__ type_ start__ end____ width___ exp.time_
 13 omega   26.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5672 -125.0000  -90.0000 58

#__ type_ start__ end____ width___ exp.time_
 14 omega   38.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -45.0000  -90.0000 60

#__ type_ start__ end____ width___ exp.time_
 15 omega   36.00  116.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -61.0000   90.0000 80

#__ type_ start__ end____ width___ exp.time_
 16 omega   73.00  120.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.8067 -125.0000  150.0000 47

#__ type_ start__ end____ width___ exp.time_
 17 omega   32.00   66.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -30.0000  150.0000 34

#__ type_ start__ end____ width___ exp.time_
 18 omega  -48.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5672   37.0000  -30.0000 84

#__ type_ start__ end____ width___ exp.time_
 19 omega  -48.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5672   37.0000  150.0000 83

#__ type_ start__ end____ width___ exp.time_
 20 omega -116.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5672  -77.0000    0.0000 106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1617285000
_diffrn_orient_matrix_UB_12      0.0255658000
_diffrn_orient_matrix_UB_13      0.0465582000
_diffrn_orient_matrix_UB_21      -0.0490342000
_diffrn_orient_matrix_UB_22      0.0972997000
_diffrn_orient_matrix_UB_23      0.0110434000
_diffrn_orient_matrix_UB_31      -0.0323423000
_diffrn_orient_matrix_UB_32      -0.0200520000
_diffrn_orient_matrix_UB_33      0.1124212000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2966
_reflns_number_total             3057
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3057
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.024
_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)+(0.0681P)²+0.9419P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1068
_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:
 C20(H20), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C16(H16A,H16B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C12(H12), C6(H6), C5(H5), C11(H11), C2(H2), C9(H9)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.81380(4) 0.57412(3) 0.25540(3) 0.01810(15) Uani 1 1 d . . . . .
O2 O 0.81834(13) 0.66738(8) 0.23544(9) 0.0235(3) Uani 1 1 d . . . . .
O1 O 0.92863(13) 0.51772(8) 0.22833(9) 0.0236(3) Uani 1 1 d . . . . .
O4 O 0.69482(13) 0.76718(8) 0.65310(9) 0.0228(3) Uani 1 1 d . . . . .
O3 O 0.89495(13) 0.69748(8) 0.73872(9) 0.0246(3) Uani 1 1 d . . . . .
N1 N 0.81348(15) 0.56074(9) 0.38559(10) 0.0177(3) Uani 1 1 d . . . . .
C13 C 0.78365(17) 0.48310(11) 0.53336(12) 0.0171(3) Uani 1 1 d . . . . .
C14 C 0.73988(18) 0.57364(10) 0.54553(12) 0.0172(3) Uani 1 1 d . . . . .
C15 C 0.75283(17) 0.61990(11) 0.45607(12) 0.0173(3) Uani 1 1 d . . . . .
C3 C 0.63177(19) 0.44702(11) 0.15108(13) 0.0201(3) Uani 1 1 d . . . . .
H3 H 0.7175 0.4126 0.1539 0.024 Uiso 1 1 calc R . . . .
C8 C 0.82670(17) 0.47508(11) 0.43301(12) 0.0175(3) Uani 1 1 d . . . . .
C19 C 0.52710(18) 0.64879(12) 0.61647(13) 0.0225(4) Uani 1 1 d . . . . .
H19A H 0.4669 0.6158 0.5598 0.027 Uiso 1 1 calc R . . . .
H19B H 0.4777 0.6487 0.6785 0.027 Uiso 1 1 calc R . . . .
C7 C 0.36475(19) 0.46478(11) 0.09845(12) 0.0210(4) Uani 1 1 d . . . . .
C4 C 0.63951(18) 0.53198(11) 0.19450(12) 0.0184(3) Uani 1 1 d . . . . .
C21 C 0.77384(19) 0.69304(11) 0.68487(12) 0.0191(3) Uani 1 1 d . . . . .
C10 C 0.86996(18) 0.32057(11) 0.46144(14) 0.0221(4) Uani 1 1 d . . . . .
H10 H 0.8966 0.2652 0.4378 0.027 Uiso 1 1 calc R . . . .
C12 C 0.78741(18) 0.40853(11) 0.59957(13) 0.0195(3) Uani 1 1 d . . . . .
H12 H 0.7617 0.4133 0.6670 0.023 Uiso 1 1 calc R . . . .
C6 C 0.37676(19) 0.55063(12) 0.14198(13) 0.0214(4) Uani 1 1 d . . . . .
H6 H 0.2915 0.5856 0.1383 0.026 Uiso 1 1 calc R . . . .
C16 C 0.72653(19) 0.71754(11) 0.43734(13) 0.0207(3) Uani 1 1 d . . . . .
H16A H 0.7270 0.7296 0.3627 0.025 Uiso 1 1 calc R . . . .
H16B H 0.8095 0.7498 0.4774 0.025 Uiso 1 1 calc R . . . .
C5 C 0.51203(19) 0.58449(11) 0.19014(13) 0.0205(4) Uani 1 1 d . . . . .
H5 H 0.5181 0.6414 0.2192 0.025 Uiso 1 1 calc R . . . .
C11 C 0.83024(19) 0.32758(11) 0.56248(13) 0.0220(4) Uani 1 1 d . . . . .
H11 H 0.8326 0.2773 0.6052 0.026 Uiso 1 1 calc R . . . .
C2 C 0.4942(2) 0.41415(11) 0.10343(13) 0.0211(4) Uani 1 1 d . . . . .
H2 H 0.4885 0.3573 0.0743 0.025 Uiso 1 1 calc R . . . .
C20 C 0.68509(18) 0.61071(10) 0.64206(12) 0.0184(3) Uani 1 1 d . . . . .
H20 H 0.6899 0.5651 0.6974 0.022 Uiso 1 1 calc R . . . .
C9 C 0.87071(18) 0.39384(11) 0.39545(13) 0.0196(3) Uani 1 1 d . . . . .
H9 H 0.8994 0.3890 0.3289 0.024 Uiso 1 1 calc R . . . .
C18 C 0.55682(18) 0.74322(12) 0.58187(13) 0.0226(4) Uani 1 1 d . . . . .
H18 H 0.4756 0.7823 0.5957 0.027 Uiso 1 1 calc R . . . .
C17 C 0.58091(19) 0.75464(12) 0.46717(13) 0.0235(4) Uani 1 1 d . . . . .
H17A H 0.5765 0.8177 0.4509 0.028 Uiso 1 1 calc R . . . .
H17B H 0.4981 0.7265 0.4217 0.028 Uiso 1 1 calc R . . . .
C1 C 0.2149(2) 0.42901(12) 0.04893(14) 0.0264(4) Uani 1 1 d . . . . .
H1A H 0.1569 0.4155 0.1036 0.040 Uiso 1 1 calc GR . . . .
H1B H 0.2284 0.3759 0.0098 0.040 Uiso 1 1 calc GR . . . .
H1C H 0.1636 0.4728 0.0018 0.040 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 O2 1.4257(13) . ?
S1 O1 1.4276(12) . ?
S1 N1 1.6741(13) . ?
S1 C4 1.7645(16) . ?
O4 C21 1.351(2) . ?
O4 C18 1.470(2) . ?
O3 C21 1.201(2) . ?
N1 C15 1.435(2) . ?
N1 C8 1.419(2) . ?
C13 C14 1.432(2) . ?
C13 C8 1.403(2) . ?
C13 C12 1.400(2) . ?
C14 C15 1.358(2) . ?
C14 C20 1.507(2) . ?
C15 C16 1.499(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.389(2) . ?
C3 C2 1.389(2) . ?
C8 C9 1.393(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.530(2) . ?
C19 C18 1.522(2) . ?
C7 C6 1.402(2) . ?
C7 C2 1.392(2) . ?
C7 C1 1.505(2) . ?
C4 C5 1.394(2) . ?
C21 C20 1.528(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.397(2) . ?
C10 C9 1.387(2) . ?
C12 H12 0.9300 . ?
C12 C11 1.383(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.379(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.537(2) . ?
C5 H5 0.9300 . ?
C11 H11 0.9300 . ?
C2 H2 0.9300 . ?
C20 H20 0.9800 . ?
C9 H9 0.9300 . ?
C18 H18 0.9800 . ?
C18 C17 1.524(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
O2 S1 O1 119.79(7) . . ?
O2 S1 N1 107.46(7) . . ?
O2 S1 C4 108.86(7) . . ?
O1 S1 N1 106.62(7) . . ?
O1 S1 C4 108.55(7) . . ?
N1 S1 C4 104.51(7) . . ?
C21 O4 C18 110.03(12) . . ?
C15 N1 S1 127.54(11) . . ?
C8 N1 S1 121.25(11) . . ?
C8 N1 C15 108.00(12) . . ?
C8 C13 C14 107.65(14) . . ?
C12 C13 C14 132.43(15) . . ?
C12 C13 C8 119.92(15) . . ?
C13 C14 C20 124.96(14) . . ?
C15 C14 C13 109.40(14) . . ?
C15 C14 C20 125.63(14) . . ?
N1 C15 C16 124.97(14) . . ?
C14 C15 N1 107.66(14) . . ?
C14 C15 C16 127.01(14) . . ?
C4 C3 H3 120.5 . . ?
C4 C3 C2 119.08(15) . . ?
C2 C3 H3 120.5 . . ?
C13 C8 N1 107.13(13) . . ?
C9 C8 N1 131.08(14) . . ?
C9 C8 C13 121.78(15) . . ?
H19A C19 H19B 109.2 . . ?
C20 C19 H19A 111.4 . . ?
C20 C19 H19B 111.4 . . ?
C18 C19 H19A 111.4 . . ?
C18 C19 H19B 111.4 . . ?
C18 C19 C20 101.94(13) . . ?
C6 C7 C1 120.19(16) . . ?
C2 C7 C6 118.22(15) . . ?
C2 C7 C1 121.59(16) . . ?
C3 C4 S1 119.34(13) . . ?
C3 C4 C5 121.03(15) . . ?
C5 C4 S1 119.63(13) . . ?
O4 C21 C20 109.61(14) . . ?
O3 C21 O4 121.26(15) . . ?
O3 C21 C20 129.13(15) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C9 C10 C11 121.86(15) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 C13 118.55(15) . . ?
C11 C12 H12 120.7 . . ?
C7 C6 H6 119.2 . . ?
C5 C6 C7 121.55(16) . . ?
C5 C6 H6 119.2 . . ?
C15 C16 H16A 108.3 . . ?
C15 C16 H16B 108.3 . . ?
C15 C16 C17 115.88(14) . . ?
H16A C16 H16B 107.4 . . ?
C17 C16 H16A 108.3 . . ?
C17 C16 H16B 108.3 . . ?
C4 C5 H5 120.6 . . ?
C6 C5 C4 118.88(15) . . ?
C6 C5 H5 120.6 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.67(15) . . ?
C12 C11 H11 119.7 . . ?
C3 C2 C7 121.24(15) . . ?
C3 C2 H2 119.4 . . ?
C7 C2 H2 119.4 . . ?
C14 C20 C19 112.59(13) . . ?
C14 C20 C21 111.55(13) . . ?
C14 C20 H20 110.4 . . ?
C19 C20 H20 110.4 . . ?
C21 C20 C19 101.31(13) . . ?
C21 C20 H20 110.4 . . ?
C8 C9 H9 121.4 . . ?
C10 C9 C8 117.19(15) . . ?
C10 C9 H9 121.4 . . ?
O4 C18 C19 102.81(13) . . ?
O4 C18 H18 109.4 . . ?
O4 C18 C17 109.13(13) . . ?
C19 C18 H18 109.4 . . ?
C19 C18 C17 116.28(14) . . ?
C17 C18 H18 109.4 . . ?
C16 C17 H17A 108.0 . . ?
C16 C17 H17B 108.0 . . ?
C18 C17 C16 117.26(14) . . ?
C18 C17 H17A 108.0 . . ?
C18 C17 H17B 108.0 . . ?
H17A C17 H17B 107.2 . . ?
C7 C1 H1A 109.5 . . ?
C7 C1 H1B 109.5 . . ?
C7 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and ethyl acetatete'
####################################################################### 
# 
# 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_y1214m
_database_code_depnum_ccdc_archive 'CCDC 1831053'
_audit_update_record             
;
2018-03-20 deposited with the CCDC.
2019-02-01 downloaded from the CCDC.
;
_audit_creation_date             2018-01-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H21 N O4 S'
_chemical_formula_sum            'C22 H21 N O4 S'
_chemical_formula_weight         395.46
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.780(3)
_cell_length_b                   9.3801(19)
_cell_length_c                   14.410(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.893(4)
_cell_angle_gamma                90
_cell_volume                     1860.2(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4468
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      2.59
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
SADABS v.2.03 (Bruker,2002) was used for absorption correction.
R(int) was 0.1003 before and 0.0329 after correction.
The Ratio of minimum to maximum transmission is 0.9124.
The λ/2 correction factor is 0.0015.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15652
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         1.995
_diffrn_ambient_temperature      273(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3644
_reflns_number_total             4240
_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       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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    'Bruker SHELXTL'
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0530
_refine_ls_restrained_S_all      1.070
_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)+(0.0674P)²+0.7351P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1365
_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:
 C18(H18), C19(H19), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16a,H16b), C20(H20a,H20b)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C17(H17a,H17b,H17c)
;
_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 0.27916(3) 0.85025(5) 0.60072(3) 0.03250(15) Uani 1 1 d . . . . .
O1 O 0.24834(11) 0.96770(16) 0.54505(11) 0.0443(4) Uani 1 1 d . . . . .
O2 O 0.27297(11) 0.85743(17) 0.69856(10) 0.0436(4) Uani 1 1 d . . . . .
O3 O 0.65348(10) 0.62953(16) 0.77180(10) 0.0401(4) Uani 1 1 d . . . . .
O4 O 0.72578(11) 0.81124(18) 0.70581(12) 0.0525(4) Uani 1 1 d . . . . .
N1 N 0.39505(11) 0.82245(17) 0.57853(11) 0.0301(4) Uani 1 1 d . . . . .
C1 C 0.08731(19) 0.3174(3) 0.44847(19) 0.0550(6) Uani 1 1 d . . . . .
H1A H 0.1155 0.2361 0.4801 0.083 Uiso 1 1 calc GR . . . .
H1B H 0.0991 0.3115 0.3835 0.083 Uiso 1 1 calc GR . . . .
H1C H 0.0186 0.3189 0.4564 0.083 Uiso 1 1 calc GR . . . .
C2 C 0.13227(15) 0.4510(2) 0.48816(15) 0.0382(5) Uani 1 1 d . . . . .
C3 C 0.16932(16) 0.4564(2) 0.57933(15) 0.0421(5) Uani 1 1 d . . . . .
H3 H 0.1647 0.3763 0.6169 0.050 Uiso 1 1 calc R . . . .
C4 C 0.21283(15) 0.5776(2) 0.61544(14) 0.0383(5) Uani 1 1 d . . . . .
H4 H 0.2375 0.5795 0.6767 0.046 Uiso 1 1 calc R . . . .
C5 C 0.21940(13) 0.6965(2) 0.55947(13) 0.0292(4) Uani 1 1 d . . . . .
C6 C 0.18203(14) 0.6945(2) 0.46871(14) 0.0352(4) Uani 1 1 d . . . . .
H6 H 0.1859 0.7749 0.4314 0.042 Uiso 1 1 calc R . . . .
C7 C 0.13915(15) 0.5720(2) 0.43433(14) 0.0395(5) Uani 1 1 d . . . . .
H7 H 0.1141 0.5705 0.3732 0.047 Uiso 1 1 calc R . . . .
C8 C 0.39005(17) 0.9087(2) 0.41054(15) 0.0400(5) Uani 1 1 d . . . . .
H8 H 0.3290 0.9510 0.4101 0.048 Uiso 1 1 calc R . . . .
C9 C 0.44457(19) 0.9091(3) 0.33296(16) 0.0487(6) Uani 1 1 d . . . . .
H9 H 0.4190 0.9519 0.2789 0.058 Uiso 1 1 calc R . . . .
C10 C 0.53612(19) 0.8480(3) 0.33265(16) 0.0483(6) Uani 1 1 d . . . . .
H10 H 0.5707 0.8508 0.2789 0.058 Uiso 1 1 calc R . . . .
C11 C 0.57612(16) 0.7834(2) 0.41087(15) 0.0399(5) Uani 1 1 d . . . . .
H11 H 0.6379 0.7434 0.4110 0.048 Uiso 1 1 calc R . . . .
C12 C 0.52246(14) 0.7790(2) 0.49007(14) 0.0313(4) Uani 1 1 d . . . . .
C13 C 0.43045(14) 0.8423(2) 0.48919(13) 0.0315(4) Uani 1 1 d . . . . .
C14 C 0.46401(13) 0.73942(19) 0.63162(13) 0.0282(4) Uani 1 1 d . . . . .
C15 C 0.54127(13) 0.7166(2) 0.57944(13) 0.0297(4) Uani 1 1 d . . . . .
C16 C 0.45387(14) 0.6999(2) 0.73133(14) 0.0337(4) Uani 1 1 d . . . . .
H16A H 0.3862 0.7115 0.7453 0.040 Uiso 1 1 calc R . . . .
H16B H 0.4911 0.7678 0.7694 0.040 Uiso 1 1 calc R . . . .
C17 C 0.47005(19) 0.5331(3) 0.86441(18) 0.0542(6) Uani 1 1 d . . . . .
H17A H 0.5150 0.5930 0.8993 0.081 Uiso 1 1 calc GR . . . .
H17B H 0.4804 0.4355 0.8823 0.081 Uiso 1 1 calc GR . . . .
H17C H 0.4048 0.5604 0.8767 0.081 Uiso 1 1 calc GR . . . .
C18 C 0.48569(15) 0.5495(2) 0.76146(15) 0.0386(5) Uani 1 1 d . . . . .
H18 H 0.4430 0.4813 0.7279 0.046 Uiso 1 1 calc R . . . .
C19 C 0.59014(15) 0.5109(2) 0.74233(16) 0.0392(5) Uani 1 1 d . . . . .
H19 H 0.6091 0.4258 0.7783 0.047 Uiso 1 1 calc R . . . .
C20 C 0.61327(15) 0.4882(2) 0.64274(15) 0.0393(5) Uani 1 1 d . . . . .
H20A H 0.5589 0.4457 0.6075 0.047 Uiso 1 1 calc R . . . .
H20B H 0.6701 0.4282 0.6378 0.047 Uiso 1 1 calc R . . . .
C21 C 0.63254(14) 0.6389(2) 0.61017(14) 0.0335(4) Uani 1 1 d . . . . .
H21 H 0.6789 0.6387 0.5608 0.040 Uiso 1 1 calc R . . . .
C22 C 0.67741(13) 0.7061(2) 0.69787(15) 0.0357(5) 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
S1 O1 1.4153(16) . ?
S1 O2 1.4183(16) . ?
S1 N1 1.6650(16) . ?
S1 C5 1.750(2) . ?
O3 C19 1.464(3) . ?
O3 C22 1.340(3) . ?
O4 C22 1.192(3) . ?
N1 C13 1.412(2) . ?
N1 C14 1.422(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.499(3) . ?
C2 C3 1.386(3) . ?
C2 C7 1.381(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(3) . ?
C5 C6 1.381(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.373(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.378(3) . ?
C8 C13 1.385(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.386(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.371(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.391(3) . ?
C12 C13 1.400(3) . ?
C12 C15 1.426(3) . ?
C14 C15 1.351(3) . ?
C14 C16 1.497(3) . ?
C15 C21 1.501(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C18 1.534(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C17 C18 1.518(3) . ?
C18 H18 0.9800 . ?
C18 C19 1.523(3) . ?
C19 H19 0.9800 . ?
C19 C20 1.501(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.517(3) . ?
C21 H21 0.9800 . ?
C21 C22 1.516(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 119.68(9) . . ?
O1 S1 N1 106.04(9) . . ?
O1 S1 C5 109.04(9) . . ?
O2 S1 N1 107.74(9) . . ?
O2 S1 C5 109.02(10) . . ?
N1 S1 C5 104.19(8) . . ?
C22 O3 C19 110.12(15) . . ?
C13 N1 S1 122.23(13) . . ?
C13 N1 C14 108.10(15) . . ?
C14 N1 S1 127.15(14) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 121.2(2) . . ?
C7 C2 C1 120.8(2) . . ?
C7 C2 C3 118.0(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.4(2) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.12(19) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 S1 120.70(15) . . ?
C6 C5 S1 118.68(15) . . ?
C6 C5 C4 120.58(19) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 C5 119.12(19) . . ?
C7 C6 H6 120.4 . . ?
C2 C7 H7 119.1 . . ?
C6 C7 C2 121.71(19) . . ?
C6 C7 H7 119.1 . . ?
C9 C8 H8 121.6 . . ?
C9 C8 C13 116.9(2) . . ?
C13 C8 H8 121.6 . . ?
C8 C9 H9 118.8 . . ?
C8 C9 C10 122.3(2) . . ?
C10 C9 H9 118.8 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.7 . . ?
C10 C11 C12 118.6(2) . . ?
C12 C11 H11 120.7 . . ?
C11 C12 C13 119.91(19) . . ?
C11 C12 C15 132.30(19) . . ?
C13 C12 C15 107.79(17) . . ?
C8 C13 N1 131.49(19) . . ?
C8 C13 C12 121.64(19) . . ?
C12 C13 N1 106.87(17) . . ?
N1 C14 C16 124.04(16) . . ?
C15 C14 N1 108.13(17) . . ?
C15 C14 C16 127.54(17) . . ?
C12 C15 C21 125.24(17) . . ?
C14 C15 C12 108.98(17) . . ?
C14 C15 C21 125.78(18) . . ?
C14 C16 H16A 108.0 . . ?
C14 C16 H16B 108.0 . . ?
C14 C16 C18 117.39(16) . . ?
H16A C16 H16B 107.2 . . ?
C18 C16 H16A 108.0 . . ?
C18 C16 H16B 108.0 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
C16 C18 H18 107.7 . . ?
C17 C18 C16 108.50(18) . . ?
C17 C18 H18 107.7 . . ?
C17 C18 C19 109.57(18) . . ?
C19 C18 C16 115.28(17) . . ?
C19 C18 H18 107.7 . . ?
O3 C19 C18 108.76(17) . . ?
O3 C19 H19 109.1 . . ?
O3 C19 C20 103.46(17) . . ?
C18 C19 H19 109.1 . . ?
C20 C19 C18 117.07(18) . . ?
C20 C19 H19 109.1 . . ?
C19 C20 H20A 111.3 . . ?
C19 C20 H20B 111.3 . . ?
C19 C20 C21 102.28(16) . . ?
H20A C20 H20B 109.2 . . ?
C21 C20 H20A 111.3 . . ?
C21 C20 H20B 111.3 . . ?
C15 C21 C20 112.75(17) . . ?
C15 C21 H21 110.7 . . ?
C15 C21 C22 110.14(15) . . ?
C20 C21 H21 110.7 . . ?
C22 C21 C20 101.54(17) . . ?
C22 C21 H21 110.7 . . ?
O3 C22 C21 109.47(17) . . ?
O4 C22 O3 121.7(2) . . ?
O4 C22 C21 128.8(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and ethyl acetate'
####################################################################### 
# 
# 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_ll-20180827
_database_code_depnum_ccdc_archive 'CCDC 1864037'
_audit_update_record             
;
2018-08-27 deposited with the CCDC.
2019-02-01 downloaded from the CCDC.
;
_audit_creation_date             2018-08-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C28 H24 N2 O7 S'
_chemical_formula_sum            'C28 H24 N2 O7 S'
_chemical_formula_weight         532.55
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   9.68936(19)
_cell_length_b                   16.6569(4)
_cell_length_c                   15.2343(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.933(2)
_cell_angle_gamma                90
_cell_volume                     2449.63(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4231
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.5160
_cell_measurement_theta_min      3.9690
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53165
_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_crystal_colour            ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9116
_diffrn_reflns_point_group_measured_fraction_full 0.698
_diffrn_reflns_point_group_measured_fraction_max 0.707
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         3.940
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4741
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   35.00   88.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -30.0000    0.0000 53

#__ type_ start__ end____ width___ exp.time_
  2 omega   63.00   89.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -45.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   39.00   93.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -45.0000 -180.0000 54

#__ type_ start__ end____ width___ exp.time_
  4 omega   34.00  107.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -94.0000 -150.0000 73

#__ type_ start__ end____ width___ exp.time_
  5 omega   33.00   86.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -30.0000  -90.0000 53

#__ type_ start__ end____ width___ exp.time_
  6 omega  130.00  175.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      109.8067   45.0000 -180.0000 45

#__ type_ start__ end____ width___ exp.time_
  7 omega   92.00  118.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      109.8067   45.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega   24.00   81.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7547 -125.0000  -60.0000 57

#__ type_ start__ end____ width___ exp.time_
  9 omega   32.00   90.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -30.0000   60.0000 58

#__ type_ start__ end____ width___ exp.time_
 10 omega  116.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  125.0000   60.0000 62

#__ type_ start__ end____ width___ exp.time_
 11 omega   75.00  103.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7547  167.0000   83.0000 28

#__ type_ start__ end____ width___ exp.time_
 12 omega    3.00   32.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7547   37.0000 -180.0000 29

#__ type_ start__ end____ width___ exp.time_
 13 omega -119.00   -8.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7547  -19.0000    0.0000 111

#__ type_ start__ end____ width___ exp.time_
 14 omega -119.00  -92.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7547 -167.0000   62.0000 27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0144513000
_diffrn_orient_matrix_UB_12      0.0262810000
_diffrn_orient_matrix_UB_13      -0.0957956000
_diffrn_orient_matrix_UB_21      -0.0310676000
_diffrn_orient_matrix_UB_22      0.0873528000
_diffrn_orient_matrix_UB_23      0.0248675000
_diffrn_orient_matrix_UB_31      0.1558207000
_diffrn_orient_matrix_UB_32      0.0150286000
_diffrn_orient_matrix_UB_33      0.0228516000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.368
_reflns_Friedel_fraction_full    0.391
_reflns_Friedel_fraction_max     0.396
_reflns_number_gt                5742
_reflns_number_total             6188
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 
;
 Flack x determined using 1413 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.05(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     687
_refine_ls_number_reflns         6188
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0570
_refine_ls_restrained_S_all      1.026
_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)+(0.1151P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1522
_refine_ls_wR_factor_ref         0.1593
_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:
 C9(H9), C37(H37)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B), C36(H36A,H36B),
 C38(H38A,H38B), C40(H40A,H40B), C41(H41A,H41B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C6(H6), C17(H17), C18(H18), C19(H19), C20(H20),
 C23(H23), C24(H24), C27(H27), C28(H28), C30(H30), C31(H31), C33(H33), C34(H34),
  C46(H46), C47(H47), C48(H48), C49(H49), C51(H51), C52(H52), C55(H55), C56(H56)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C54(H54A,H54B,H54C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.02222(12) 0.42571(7) 0.43386(8) 0.0272(3) Uani 1 1 d . . . . .
O1 O 0.6325(4) 1.1839(2) 0.3571(3) 0.0384(9) Uani 1 1 d . . . . .
O2 O 0.8430(4) 1.1450(2) 0.3476(3) 0.0364(9) Uani 1 1 d . . . . .
O3 O 0.6199(4) 0.7483(2) 0.3653(3) 0.0346(9) Uani 1 1 d . . . . .
O4 O 0.4083(4) 0.7984(2) 0.3219(3) 0.0317(8) Uani 1 1 d . . . . .
O5 O 0.0575(4) 0.8237(2) 0.3426(3) 0.0359(9) Uani 1 1 d . . . . .
O6 O -0.0790(4) 0.4628(2) 0.4838(2) 0.0337(8) Uani 1 1 d . . . . .
O7 O 0.0845(4) 0.3527(2) 0.4648(3) 0.0338(8) Uani 1 1 d . . . . .
N1 N 0.1498(4) 0.4926(3) 0.4261(3) 0.0289(9) Uani 1 1 d . . . . .
N006 N 0.7195(5) 1.1316(3) 0.3526(3) 0.0298(10) Uani 1 1 d . . . . .
C1 C 0.5341(6) 1.0313(4) 0.3471(4) 0.0349(12) Uani 1 1 d . . . . .
H1 H 0.4684 1.0737 0.3439 0.042 Uiso 1 1 calc R . . . .
C2 C 0.6747(5) 1.0473(3) 0.3529(3) 0.0283(11) Uani 1 1 d . . . . .
C3 C 0.7731(5) 0.9873(3) 0.3581(3) 0.0286(11) Uani 1 1 d . . . . .
H3 H 0.8690 0.9999 0.3613 0.034 Uiso 1 1 calc R . . . .
C4 C 0.7292(5) 0.9086(3) 0.3584(3) 0.0271(10) Uani 1 1 d . . . . .
H4 H 0.7954 0.8664 0.3633 0.033 Uiso 1 1 calc R . . . .
C5 C 0.5874(5) 0.8906(3) 0.3517(3) 0.0279(10) Uani 1 1 d . . . . .
C6 C 0.4919(5) 0.9524(4) 0.3460(4) 0.0357(12) Uani 1 1 d . . . . .
H6 H 0.3957 0.9402 0.3413 0.043 Uiso 1 1 calc R . . . .
C7 C 0.5448(5) 0.8048(3) 0.3484(3) 0.0279(10) Uani 1 1 d . . . . .
C8 C 0.3515(5) 0.7178(3) 0.3210(3) 0.0278(10) Uani 1 1 d . . . . .
H8A H 0.4204 0.6793 0.3014 0.033 Uiso 1 1 calc R . . . .
H8B H 0.2678 0.7151 0.2790 0.033 Uiso 1 1 calc R . . . .
C9 C 0.3142(5) 0.6952(3) 0.4129(4) 0.0281(11) Uani 1 1 d . . . . .
H9 H 0.4016 0.6987 0.4527 0.034 Uiso 1 1 calc R . . . .
C10 C 0.2112(5) 0.7563(3) 0.4484(3) 0.0284(10) Uani 1 1 d . . . . .
H10A H 0.1865 0.7385 0.5070 0.034 Uiso 1 1 calc R . . . .
H10B H 0.2569 0.8094 0.4556 0.034 Uiso 1 1 calc R . . . .
C11 C 0.0804(5) 0.7646(3) 0.3869(3) 0.0284(11) Uani 1 1 d . . . . .
C12 C -0.0187(5) 0.6943(3) 0.3791(4) 0.0293(11) Uani 1 1 d . . . . .
H12A H -0.0216 0.6741 0.3179 0.035 Uiso 1 1 calc R . . . .
H12B H -0.1123 0.7150 0.3879 0.035 Uiso 1 1 calc R . . . .
C13 C 0.0087(5) 0.6225(3) 0.4408(4) 0.0301(11) Uani 1 1 d . . . . .
H13A H 0.0133 0.6416 0.5025 0.036 Uiso 1 1 calc R . . . .
H13B H -0.0701 0.5847 0.4320 0.036 Uiso 1 1 calc R . . . .
C14 C 0.1410(5) 0.5781(3) 0.4266(3) 0.0260(10) Uani 1 1 d . . . . .
C15 C 0.2677(5) 0.6083(3) 0.4136(3) 0.0250(10) Uani 1 1 d . . . . .
C16 C 0.3603(5) 0.5422(3) 0.4021(3) 0.0271(10) Uani 1 1 d . . . . .
C17 C 0.5015(5) 0.5390(4) 0.3883(3) 0.0323(11) Uani 1 1 d . . . . .
H17 H 0.5533 0.5870 0.3837 0.039 Uiso 1 1 calc R . . . .
C18 C 0.5638(6) 0.4653(4) 0.3814(4) 0.0391(13) Uani 1 1 d . . . . .
H18 H 0.6597 0.4626 0.3729 0.047 Uiso 1 1 calc R . . . .
C19 C 0.4883(6) 0.3946(4) 0.3866(4) 0.0378(12) Uani 1 1 d . . . . .
H19 H 0.5333 0.3446 0.3801 0.045 Uiso 1 1 calc R . . . .
C20 C 0.3487(6) 0.3956(3) 0.4012(4) 0.0338(12) Uani 1 1 d . . . . .
H20 H 0.2977 0.3472 0.4053 0.041 Uiso 1 1 calc R . . . .
C21 C 0.2866(5) 0.4705(3) 0.4095(3) 0.0284(10) Uani 1 1 d . . . . .
C22 C -0.0510(5) 0.4106(3) 0.3233(3) 0.0269(10) Uani 1 1 d . . . . .
C23 C -0.1024(6) 0.3340(4) 0.3061(4) 0.0365(12) Uani 1 1 d . . . . .
H23 H -0.0915 0.2927 0.3491 0.044 Uiso 1 1 calc R . . . .
C24 C -0.1700(6) 0.3201(4) 0.2241(4) 0.0424(14) Uani 1 1 d . . . . .
H24 H -0.2067 0.2682 0.2109 0.051 Uiso 1 1 calc R . . . .
C25 C -0.1859(6) 0.3791(4) 0.1607(4) 0.0350(12) Uani 1 1 d . . . . .
C26 C -0.2553(7) 0.3594(5) 0.0706(4) 0.0465(15) Uani 1 1 d . . . . .
H26A H -0.2688 0.4089 0.0361 0.070 Uiso 1 1 calc GR . . . .
H26B H -0.3453 0.3343 0.0770 0.070 Uiso 1 1 calc GR . . . .
H26C H -0.1967 0.3223 0.0404 0.070 Uiso 1 1 calc GR . . . .
C27 C -0.1334(5) 0.4556(4) 0.1802(3) 0.0308(11) Uani 1 1 d . . . . .
H27 H -0.1430 0.4969 0.1371 0.037 Uiso 1 1 calc R . . . .
C28 C -0.0665(5) 0.4713(3) 0.2635(3) 0.0296(10) Uani 1 1 d . . . . .
H28 H -0.0325 0.5235 0.2781 0.036 Uiso 1 1 calc R . . . .
S2 S -0.01807(13) 0.56073(8) 0.91121(8) 0.0310(3) Uani 1 1 d . . . . .
O8 O 0.6178(5) -0.1825(3) 0.8296(3) 0.0479(11) Uani 1 1 d . . . . .
O9 O 0.8332(5) -0.1489(3) 0.8511(4) 0.0626(15) Uani 1 1 d . . . . .
O10 O 0.6319(4) 0.2475(2) 0.9011(3) 0.0424(10) Uani 1 1 d . . . . .
O11 O 0.4290(4) 0.1951(3) 0.9344(3) 0.0385(9) Uani 1 1 d . . . . .
O12 O 0.0498(5) 0.1560(3) 0.8453(3) 0.0457(10) Uani 1 1 d . . . . .
O13 O -0.1193(4) 0.5128(3) 0.9496(3) 0.0418(10) Uani 1 1 d . . . . .
O14 O 0.0336(4) 0.6309(2) 0.9563(3) 0.0411(10) Uani 1 1 d . . . . .
N2 N 0.7100(6) -0.1325(3) 0.8441(3) 0.0385(11) Uani 1 1 d . . . . .
N3 N 0.1174(5) 0.5014(3) 0.8980(3) 0.0311(10) Uani 1 1 d . . . . .
C29 C 0.6702(6) -0.0476(3) 0.8549(3) 0.0322(11) Uani 1 1 d . . . . .
C30 C 0.5306(6) -0.0300(4) 0.8517(5) 0.0430(14) Uani 1 1 d . . . . .
H30 H 0.4623 -0.0699 0.8375 0.052 Uiso 1 1 calc R . . . .
C31 C 0.4941(6) 0.0488(4) 0.8701(5) 0.0432(14) Uani 1 1 d . . . . .
H31 H 0.3992 0.0628 0.8713 0.052 Uiso 1 1 calc R . . . .
C32 C 0.5947(6) 0.1062(3) 0.8866(4) 0.0321(11) Uani 1 1 d . . . . .
C33 C 0.7326(6) 0.0867(4) 0.8849(4) 0.0353(12) Uani 1 1 d . . . . .
H33 H 0.8011 0.1274 0.8935 0.042 Uiso 1 1 calc R . . . .
C34 C 0.7719(6) 0.0086(4) 0.8708(4) 0.0363(12) Uani 1 1 d . . . . .
H34 H 0.8670 -0.0057 0.8721 0.044 Uiso 1 1 calc R . . . .
C35 C 0.5572(6) 0.1915(4) 0.9073(4) 0.0361(12) Uani 1 1 d . . . . .
C36 C 0.3759(6) 0.2741(4) 0.9517(4) 0.0404(13) Uani 1 1 d . . . . .
H36A H 0.4520 0.3084 0.9781 0.048 Uiso 1 1 calc R . . . .
H36B H 0.3047 0.2699 0.9944 0.048 Uiso 1 1 calc R . . . .
C37 C 0.3126(6) 0.3124(3) 0.8665(4) 0.0330(12) Uani 1 1 d . . . . .
H37 H 0.3910 0.3205 0.8288 0.040 Uiso 1 1 calc R . . . .
C38 C 0.2101(6) 0.2561(3) 0.8145(3) 0.0314(11) Uani 1 1 d . . . . .
H38A H 0.1715 0.2852 0.7613 0.038 Uiso 1 1 calc R . . . .
H38B H 0.2632 0.2099 0.7941 0.038 Uiso 1 1 calc R . . . .
C39 C 0.0898(6) 0.2232(3) 0.8608(4) 0.0338(12) Uani 1 1 d . . . . .
C40 C 0.0175(6) 0.2781(4) 0.9197(4) 0.0395(13) Uani 1 1 d . . . . .
H40A H 0.0724 0.2804 0.9776 0.047 Uiso 1 1 calc R . . . .
H40B H -0.0735 0.2543 0.9295 0.047 Uiso 1 1 calc R . . . .
C41 C -0.0062(6) 0.3642(4) 0.8860(5) 0.0397(13) Uani 1 1 d . . . . .
H41A H -0.0463 0.3619 0.8240 0.048 Uiso 1 1 calc R . . . .
H41B H -0.0751 0.3903 0.9210 0.048 Uiso 1 1 calc R . . . .
C42 C 0.1231(5) 0.4158(3) 0.8905(3) 0.0301(11) Uani 1 1 d . . . . .
C43 C 0.2561(5) 0.3950(3) 0.8830(3) 0.0306(11) Uani 1 1 d . . . . .
C44 C 0.3396(6) 0.4661(4) 0.8853(3) 0.0328(11) Uani 1 1 d . . . . .
C45 C 0.2527(5) 0.5322(3) 0.8897(3) 0.0303(11) Uani 1 1 d . . . . .
C46 C 0.3014(7) 0.6107(4) 0.8860(4) 0.0384(13) Uani 1 1 d . . . . .
H46 H 0.2414 0.6555 0.8896 0.046 Uiso 1 1 calc R . . . .
C47 C 0.4400(7) 0.6204(4) 0.8768(4) 0.0488(16) Uani 1 1 d . . . . .
H47 H 0.4754 0.6731 0.8710 0.059 Uiso 1 1 calc R . . . .
C48 C 0.5309(7) 0.5554(5) 0.8758(4) 0.0499(16) Uani 1 1 d . . . . .
H48 H 0.6272 0.5647 0.8731 0.060 Uiso 1 1 calc R . . . .
C49 C 0.4815(6) 0.4776(4) 0.8785(4) 0.0391(13) Uani 1 1 d . . . . .
H49 H 0.5423 0.4331 0.8759 0.047 Uiso 1 1 calc R . . . .
C50 C -0.0840(5) 0.5889(3) 0.8042(3) 0.0282(10) Uani 1 1 d . . . . .
C51 C -0.1165(6) 0.6689(4) 0.7904(4) 0.0369(12) Uani 1 1 d . . . . .
H51 H -0.0959 0.7072 0.8359 0.044 Uiso 1 1 calc R . . . .
C52 C -0.1789(6) 0.6925(4) 0.7102(4) 0.0362(12) Uani 1 1 d . . . . .
H52 H -0.2035 0.7473 0.7011 0.043 Uiso 1 1 calc R . . . .
C53 C -0.2069(5) 0.6379(4) 0.6421(4) 0.0328(12) Uani 1 1 d . . . . .
C54 C -0.2796(6) 0.6662(4) 0.5556(4) 0.0405(13) Uani 1 1 d . . . . .
H54A H -0.3754 0.6809 0.5645 0.061 Uiso 1 1 calc GR . . . .
H54B H -0.2795 0.6230 0.5120 0.061 Uiso 1 1 calc GR . . . .
H54C H -0.2311 0.7131 0.5345 0.061 Uiso 1 1 calc GR . . . .
C55 C -0.1703(5) 0.5585(4) 0.6569(3) 0.0309(11) Uani 1 1 d . . . . .
H55 H -0.1878 0.5205 0.6108 0.037 Uiso 1 1 calc R . . . .
C56 C -0.1090(5) 0.5334(3) 0.7371(4) 0.0316(11) Uani 1 1 d . . . . .
H56 H -0.0842 0.4787 0.7462 0.038 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 O6 1.433(4) . ?
S1 O7 1.421(4) . ?
S1 N1 1.676(5) . ?
S1 C22 1.788(5) . ?
O1 N006 1.218(6) . ?
O2 N006 1.227(6) . ?
O3 C7 1.204(7) . ?
O4 C7 1.353(6) . ?
O4 C8 1.452(6) . ?
O5 C11 1.204(7) . ?
N1 C14 1.426(7) . ?
N1 C21 1.419(7) . ?
N006 C2 1.470(7) . ?
C1 H1 0.9500 . ?
C1 C2 1.383(8) . ?
C1 C6 1.376(9) . ?
C2 C3 1.379(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.378(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.402(7) . ?
C5 C6 1.382(8) . ?
C5 C7 1.487(8) . ?
C6 H6 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.524(7) . ?
C9 H9 1.0000 . ?
C9 C10 1.554(7) . ?
C9 C15 1.516(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.516(7) . ?
C11 C12 1.512(7) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.530(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.512(7) . ?
C14 C15 1.357(7) . ?
C15 C16 1.441(7) . ?
C16 C17 1.403(7) . ?
C16 C21 1.402(7) . ?
C17 H17 0.9500 . ?
C17 C18 1.377(8) . ?
C18 H18 0.9500 . ?
C18 C19 1.392(9) . ?
C19 H19 0.9500 . ?
C19 C20 1.389(8) . ?
C20 H20 0.9500 . ?
C20 C21 1.396(8) . ?
C22 C23 1.387(8) . ?
C22 C28 1.360(7) . ?
C23 H23 0.9500 . ?
C23 C24 1.380(9) . ?
C24 H24 0.9500 . ?
C24 C25 1.377(9) . ?
C25 C26 1.512(8) . ?
C25 C27 1.394(8) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27 0.9500 . ?
C27 C28 1.399(7) . ?
C28 H28 0.9500 . ?
S2 O13 1.428(4) . ?
S2 O14 1.425(4) . ?
S2 N3 1.669(5) . ?
S2 C50 1.762(5) . ?
O8 N2 1.228(7) . ?
O9 N2 1.220(7) . ?
O10 C35 1.190(7) . ?
O11 C35 1.344(7) . ?
O11 C36 1.446(7) . ?
O12 C39 1.201(7) . ?
N2 C29 1.479(7) . ?
N3 C42 1.432(7) . ?
N3 C45 1.423(7) . ?
C29 C30 1.381(8) . ?
C29 C34 1.366(9) . ?
C30 H30 0.9500 . ?
C30 C31 1.394(9) . ?
C31 H31 0.9500 . ?
C31 C32 1.374(9) . ?
C32 C33 1.377(8) . ?
C32 C35 1.506(8) . ?
C33 H33 0.9500 . ?
C33 C34 1.377(9) . ?
C34 H34 0.9500 . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C36 C37 1.527(8) . ?
C37 H37 1.0000 . ?
C37 C38 1.535(7) . ?
C37 C43 1.511(7) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C38 C39 1.516(8) . ?
C39 C40 1.497(8) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C40 C41 1.534(8) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C41 C42 1.516(8) . ?
C42 C43 1.348(7) . ?
C43 C44 1.433(8) . ?
C44 C45 1.391(8) . ?
C44 C49 1.400(8) . ?
C45 C46 1.393(8) . ?
C46 H46 0.9500 . ?
C46 C47 1.372(9) . ?
C47 H47 0.9500 . ?
C47 C48 1.396(11) . ?
C48 H48 0.9500 . ?
C48 C49 1.383(10) . ?
C49 H49 0.9500 . ?
C50 C51 1.381(8) . ?
C50 C56 1.384(8) . ?
C51 H51 0.9500 . ?
C51 C52 1.374(8) . ?
C52 H52 0.9500 . ?
C52 C53 1.388(8) . ?
C53 C54 1.515(8) . ?
C53 C55 1.382(8) . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
C55 H55 0.9500 . ?
C55 C56 1.377(8) . ?
C56 H56 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
O6 S1 N1 107.1(2) . . ?
O6 S1 C22 109.1(2) . . ?
O7 S1 O6 118.9(2) . . ?
O7 S1 N1 107.4(2) . . ?
O7 S1 C22 108.4(2) . . ?
N1 S1 C22 105.2(2) . . ?
C7 O4 C8 115.9(4) . . ?
C14 N1 S1 128.2(4) . . ?
C21 N1 S1 123.0(4) . . ?
C21 N1 C14 108.5(4) . . ?
O1 N006 O2 123.8(5) . . ?
O1 N006 C2 118.5(4) . . ?
O2 N006 C2 117.6(4) . . ?
C2 C1 H1 120.8 . . ?
C6 C1 H1 120.8 . . ?
C6 C1 C2 118.4(5) . . ?
C1 C2 N006 118.3(5) . . ?
C3 C2 N006 119.3(4) . . ?
C3 C2 C1 122.4(5) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 C2 118.6(5) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.3(5) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C7 118.4(5) . . ?
C6 C5 C4 119.5(5) . . ?
C6 C5 C7 122.1(5) . . ?
C1 C6 C5 120.9(5) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
O3 C7 O4 124.0(5) . . ?
O3 C7 C5 125.7(5) . . ?
O4 C7 C5 110.3(4) . . ?
O4 C8 H8A 109.7 . . ?
O4 C8 H8B 109.7 . . ?
O4 C8 C9 109.8(4) . . ?
H8A C8 H8B 108.2 . . ?
C9 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
C8 C9 H9 106.7 . . ?
C8 C9 C10 111.6(4) . . ?
C10 C9 H9 106.7 . . ?
C15 C9 C8 109.6(4) . . ?
C15 C9 H9 106.7 . . ?
C15 C9 C10 115.0(4) . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 C9 111.9(4) . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
O5 C11 C10 121.6(5) . . ?
O5 C11 C12 120.3(5) . . ?
C12 C11 C10 118.0(4) . . ?
C11 C12 H12A 107.6 . . ?
C11 C12 H12B 107.6 . . ?
C11 C12 C13 118.8(4) . . ?
H12A C12 H12B 107.0 . . ?
C13 C12 H12A 107.6 . . ?
C13 C12 H12B 107.6 . . ?
C12 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 C12 113.6(4) . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
N1 C14 C13 122.8(5) . . ?
C15 C14 N1 108.3(4) . . ?
C15 C14 C13 128.9(5) . . ?
C14 C15 C9 128.9(5) . . ?
C14 C15 C16 108.3(4) . . ?
C16 C15 C9 122.7(4) . . ?
C17 C16 C15 132.3(5) . . ?
C21 C16 C15 108.4(4) . . ?
C21 C16 C17 119.3(5) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 C16 119.0(5) . . ?
C18 C17 H17 120.5 . . ?
C17 C18 H18 119.5 . . ?
C17 C18 C19 120.9(5) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 H19 119.2 . . ?
C20 C19 C18 121.6(5) . . ?
C20 C19 H19 119.2 . . ?
C19 C20 H20 121.4 . . ?
C19 C20 C21 117.3(5) . . ?
C21 C20 H20 121.4 . . ?
C16 C21 N1 106.4(4) . . ?
C20 C21 N1 131.7(5) . . ?
C20 C21 C16 121.9(4) . . ?
C23 C22 S1 114.5(4) . . ?
C28 C22 S1 122.6(4) . . ?
C28 C22 C23 122.6(5) . . ?
C22 C23 H23 121.3 . . ?
C24 C23 C22 117.4(5) . . ?
C24 C23 H23 121.3 . . ?
C23 C24 H24 119.0 . . ?
C25 C24 C23 122.1(6) . . ?
C25 C24 H24 119.0 . . ?
C24 C25 C26 119.7(6) . . ?
C24 C25 C27 119.1(5) . . ?
C27 C25 C26 121.1(6) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27 120.2 . . ?
C25 C27 C28 119.7(5) . . ?
C28 C27 H27 120.2 . . ?
C22 C28 C27 119.0(5) . . ?
C22 C28 H28 120.5 . . ?
C27 C28 H28 120.5 . . ?
O13 S2 N3 107.1(2) . . ?
O13 S2 C50 108.7(2) . . ?
O14 S2 O13 119.1(3) . . ?
O14 S2 N3 107.2(2) . . ?
O14 S2 C50 108.1(3) . . ?
N3 S2 C50 105.8(2) . . ?
C35 O11 C36 116.7(5) . . ?
O8 N2 C29 118.5(5) . . ?
O9 N2 O8 123.7(5) . . ?
O9 N2 C29 117.9(5) . . ?
C42 N3 S2 129.4(4) . . ?
C45 N3 S2 122.5(4) . . ?
C45 N3 C42 108.0(4) . . ?
C30 C29 N2 117.6(5) . . ?
C34 C29 N2 119.0(5) . . ?
C34 C29 C30 123.4(6) . . ?
C29 C30 H30 121.4 . . ?
C29 C30 C31 117.2(6) . . ?
C31 C30 H30 121.4 . . ?
C30 C31 H31 119.9 . . ?
C32 C31 C30 120.2(5) . . ?
C32 C31 H31 119.9 . . ?
C31 C32 C33 120.5(5) . . ?
C31 C32 C35 121.0(5) . . ?
C33 C32 C35 118.6(5) . . ?
C32 C33 H33 119.8 . . ?
C34 C33 C32 120.5(5) . . ?
C34 C33 H33 119.8 . . ?
C29 C34 C33 118.1(5) . . ?
C29 C34 H34 121.0 . . ?
C33 C34 H34 121.0 . . ?
O10 C35 O11 125.0(5) . . ?
O10 C35 C32 124.3(5) . . ?
O11 C35 C32 110.7(5) . . ?
O11 C36 H36A 109.6 . . ?
O11 C36 H36B 109.6 . . ?
O11 C36 C37 110.3(5) . . ?
H36A C36 H36B 108.1 . . ?
C37 C36 H36A 109.6 . . ?
C37 C36 H36B 109.6 . . ?
C36 C37 H37 106.0 . . ?
C36 C37 C38 112.3(5) . . ?
C38 C37 H37 106.0 . . ?
C43 C37 C36 111.3(5) . . ?
C43 C37 H37 106.0 . . ?
C43 C37 C38 114.5(4) . . ?
C37 C38 H38A 107.8 . . ?
C37 C38 H38B 107.8 . . ?
H38A C38 H38B 107.1 . . ?
C39 C38 C37 118.0(5) . . ?
C39 C38 H38A 107.8 . . ?
C39 C38 H38B 107.8 . . ?
O12 C39 C38 119.5(5) . . ?
O12 C39 C40 121.8(5) . . ?
C40 C39 C38 118.5(5) . . ?
C39 C40 H40A 108.3 . . ?
C39 C40 H40B 108.3 . . ?
C39 C40 C41 115.7(5) . . ?
H40A C40 H40B 107.4 . . ?
C41 C40 H40A 108.3 . . ?
C41 C40 H40B 108.3 . . ?
C40 C41 H41A 108.6 . . ?
C40 C41 H41B 108.6 . . ?
H41A C41 H41B 107.6 . . ?
C42 C41 C40 114.6(5) . . ?
C42 C41 H41A 108.6 . . ?
C42 C41 H41B 108.6 . . ?
N3 C42 C41 122.1(5) . . ?
C43 C42 N3 107.8(5) . . ?
C43 C42 C41 130.0(5) . . ?
C42 C43 C37 127.6(5) . . ?
C42 C43 C44 109.1(5) . . ?
C44 C43 C37 123.0(5) . . ?
C45 C44 C43 108.2(4) . . ?
C45 C44 C49 119.8(6) . . ?
C49 C44 C43 131.9(6) . . ?
C44 C45 N3 106.6(5) . . ?
C44 C45 C46 122.2(5) . . ?
C46 C45 N3 131.3(5) . . ?
C45 C46 H46 121.6 . . ?
C47 C46 C45 116.9(6) . . ?
C47 C46 H46 121.6 . . ?
C46 C47 H47 118.9 . . ?
C46 C47 C48 122.3(6) . . ?
C48 C47 H47 118.9 . . ?
C47 C48 H48 119.8 . . ?
C49 C48 C47 120.4(6) . . ?
C49 C48 H48 119.8 . . ?
C44 C49 H49 120.8 . . ?
C48 C49 C44 118.4(6) . . ?
C48 C49 H49 120.8 . . ?
C51 C50 S2 117.2(4) . . ?
C51 C50 C56 120.6(5) . . ?
C56 C50 S2 122.1(4) . . ?
C50 C51 H51 120.4 . . ?
C52 C51 C50 119.3(5) . . ?
C52 C51 H51 120.4 . . ?
C51 C52 H52 119.3 . . ?
C51 C52 C53 121.3(5) . . ?
C53 C52 H52 119.3 . . ?
C52 C53 C54 119.5(5) . . ?
C55 C53 C52 118.3(5) . . ?
C55 C53 C54 122.2(5) . . ?
C53 C54 H54A 109.5 . . ?
C53 C54 H54B 109.5 . . ?
C53 C54 H54C 109.5 . . ?
H54A C54 H54B 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C53 C55 H55 119.3 . . ?
C56 C55 C53 121.4(5) . . ?
C56 C55 H55 119.3 . . ?
C50 C56 H56 120.4 . . ?
C55 C56 C50 119.2(5) . . ?
C55 C56 H56 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C14 C13 4.1(8) . . . . ?
S1 N1 C14 C15 -176.5(4) . . . . ?
S1 N1 C21 C16 176.4(4) . . . . ?
S1 N1 C21 C20 -4.0(8) . . . . ?
S1 C22 C23 C24 175.1(5) . . . . ?
S1 C22 C28 C27 -175.7(4) . . . . ?
O1 N006 C2 C1 7.9(7) . . . . ?
O1 N006 C2 C3 -172.6(5) . . . . ?
O2 N006 C2 C1 -171.9(5) . . . . ?
O2 N006 C2 C3 7.6(7) . . . . ?
O4 C8 C9 C10 56.7(5) . . . . ?
O4 C8 C9 C15 -174.7(4) . . . . ?
O5 C11 C12 C13 -176.0(5) . . . . ?
O6 S1 N1 C14 -28.6(5) . . . . ?
O6 S1 N1 C21 157.3(4) . . . . ?
O6 S1 C22 C23 -97.4(4) . . . . ?
O6 S1 C22 C28 76.8(5) . . . . ?
O7 S1 N1 C14 -157.4(4) . . . . ?
O7 S1 N1 C21 28.6(5) . . . . ?
O7 S1 C22 C23 33.4(5) . . . . ?
O7 S1 C22 C28 -152.4(4) . . . . ?
N1 S1 C22 C23 148.0(4) . . . . ?
N1 S1 C22 C28 -37.8(5) . . . . ?
N1 C14 C15 C9 -176.8(5) . . . . ?
N1 C14 C15 C16 1.5(6) . . . . ?
N006 C2 C3 C4 179.8(5) . . . . ?
C1 C2 C3 C4 -0.7(8) . . . . ?
C2 C1 C6 C5 0.8(9) . . . . ?
C2 C3 C4 C5 1.4(8) . . . . ?
C3 C4 C5 C6 -1.0(8) . . . . ?
C3 C4 C5 C7 177.4(5) . . . . ?
C4 C5 C6 C1 -0.1(9) . . . . ?
C4 C5 C7 O3 12.9(8) . . . . ?
C4 C5 C7 O4 -166.0(4) . . . . ?
C6 C1 C2 N006 179.1(5) . . . . ?
C6 C1 C2 C3 -0.4(9) . . . . ?
C6 C5 C7 O3 -168.8(5) . . . . ?
C6 C5 C7 O4 12.3(7) . . . . ?
C7 O4 C8 C9 83.2(5) . . . . ?
C7 C5 C6 C1 -178.4(5) . . . . ?
C8 O4 C7 O3 4.6(7) . . . . ?
C8 O4 C7 C5 -176.4(4) . . . . ?
C8 C9 C10 C11 56.6(5) . . . . ?
C8 C9 C15 C14 -114.5(6) . . . . ?
C8 C9 C15 C16 67.4(6) . . . . ?
C9 C10 C11 O5 -107.6(5) . . . . ?
C9 C10 C11 C12 69.5(6) . . . . ?
C9 C15 C16 C17 -0.4(8) . . . . ?
C9 C15 C16 C21 177.8(5) . . . . ?
C10 C9 C15 C14 12.2(8) . . . . ?
C10 C9 C15 C16 -165.9(4) . . . . ?
C10 C11 C12 C13 6.9(7) . . . . ?
C11 C12 C13 C14 -64.7(6) . . . . ?
C12 C13 C14 N1 -137.5(5) . . . . ?
C12 C13 C14 C15 43.3(7) . . . . ?
C13 C14 C15 C9 2.4(9) . . . . ?
C13 C14 C15 C16 -179.2(5) . . . . ?
C14 N1 C21 C16 1.3(5) . . . . ?
C14 N1 C21 C20 -179.1(5) . . . . ?
C14 C15 C16 C17 -178.8(5) . . . . ?
C14 C15 C16 C21 -0.7(5) . . . . ?
C15 C9 C10 C11 -69.1(6) . . . . ?
C15 C16 C17 C18 178.6(5) . . . . ?
C15 C16 C21 N1 -0.4(5) . . . . ?
C15 C16 C21 C20 179.9(5) . . . . ?
C16 C17 C18 C19 1.0(8) . . . . ?
C17 C16 C21 N1 178.0(4) . . . . ?
C17 C16 C21 C20 -1.6(7) . . . . ?
C17 C18 C19 C20 -1.6(9) . . . . ?
C18 C19 C20 C21 0.6(8) . . . . ?
C19 C20 C21 N1 -178.5(5) . . . . ?
C19 C20 C21 C16 1.0(8) . . . . ?
C21 N1 C14 C13 178.9(4) . . . . ?
C21 N1 C14 C15 -1.8(6) . . . . ?
C21 C16 C17 C18 0.6(7) . . . . ?
C22 S1 N1 C14 87.3(5) . . . . ?
C22 S1 N1 C21 -86.7(4) . . . . ?
C22 C23 C24 C25 0.4(9) . . . . ?
C23 C22 C28 C27 -1.9(8) . . . . ?
C23 C24 C25 C26 177.3(6) . . . . ?
C23 C24 C25 C27 -0.6(9) . . . . ?
C24 C25 C27 C28 -0.4(8) . . . . ?
C25 C27 C28 C22 1.7(8) . . . . ?
C26 C25 C27 C28 -178.3(5) . . . . ?
C28 C22 C23 C24 0.9(9) . . . . ?
S2 N3 C42 C41 5.4(8) . . . . ?
S2 N3 C42 C43 -178.4(4) . . . . ?
S2 N3 C45 C44 176.4(4) . . . . ?
S2 N3 C45 C46 -3.6(8) . . . . ?
S2 C50 C51 C52 -174.6(4) . . . . ?
S2 C50 C56 C55 175.1(4) . . . . ?
O8 N2 C29 C30 2.8(8) . . . . ?
O8 N2 C29 C34 -179.8(5) . . . . ?
O9 N2 C29 C30 -176.6(6) . . . . ?
O9 N2 C29 C34 0.8(8) . . . . ?
O11 C36 C37 C38 50.0(6) . . . . ?
O11 C36 C37 C43 179.9(5) . . . . ?
O12 C39 C40 C41 -134.9(6) . . . . ?
O13 S2 N3 C42 23.4(6) . . . . ?
O13 S2 N3 C45 -158.5(4) . . . . ?
O13 S2 C50 C51 110.8(5) . . . . ?
O13 S2 C50 C56 -66.2(5) . . . . ?
O14 S2 N3 C42 152.3(5) . . . . ?
O14 S2 N3 C45 -29.6(5) . . . . ?
O14 S2 C50 C51 -19.8(5) . . . . ?
O14 S2 C50 C56 163.1(4) . . . . ?
N2 C29 C30 C31 174.1(6) . . . . ?
N2 C29 C34 C33 -176.9(5) . . . . ?
N3 S2 C50 C51 -134.5(4) . . . . ?
N3 S2 C50 C56 48.5(5) . . . . ?
N3 C42 C43 C37 -174.9(5) . . . . ?
N3 C42 C43 C44 -0.2(6) . . . . ?
N3 C45 C46 C47 -179.4(5) . . . . ?
C29 C30 C31 C32 2.9(10) . . . . ?
C30 C29 C34 C33 0.4(9) . . . . ?
C30 C31 C32 C33 0.1(10) . . . . ?
C30 C31 C32 C35 -179.5(6) . . . . ?
C31 C32 C33 C34 -3.1(9) . . . . ?
C31 C32 C35 O10 -160.8(6) . . . . ?
C31 C32 C35 O11 19.7(8) . . . . ?
C32 C33 C34 C29 2.8(9) . . . . ?
C33 C32 C35 O10 19.6(9) . . . . ?
C33 C32 C35 O11 -159.9(5) . . . . ?
C34 C29 C30 C31 -3.3(10) . . . . ?
C35 O11 C36 C37 84.2(6) . . . . ?
C35 C32 C33 C34 176.5(5) . . . . ?
C36 O11 C35 O10 4.1(8) . . . . ?
C36 O11 C35 C32 -176.5(5) . . . . ?
C36 C37 C38 C39 56.1(6) . . . . ?
C36 C37 C43 C42 -100.2(6) . . . . ?
C36 C37 C43 C44 85.7(6) . . . . ?
C37 C38 C39 O12 -144.1(6) . . . . ?
C37 C38 C39 C40 40.4(7) . . . . ?
C37 C43 C44 C45 171.9(5) . . . . ?
C37 C43 C44 C49 -3.7(9) . . . . ?
C38 C37 C43 C42 28.5(8) . . . . ?
C38 C37 C43 C44 -145.6(5) . . . . ?
C38 C39 C40 C41 40.6(8) . . . . ?
C39 C40 C41 C42 -73.3(7) . . . . ?
C40 C41 C42 N3 -153.4(5) . . . . ?
C40 C41 C42 C43 31.3(9) . . . . ?
C41 C42 C43 C37 0.9(10) . . . . ?
C41 C42 C43 C44 175.7(6) . . . . ?
C42 N3 C45 C44 -5.1(6) . . . . ?
C42 N3 C45 C46 174.9(6) . . . . ?
C42 C43 C44 C45 -3.1(6) . . . . ?
C42 C43 C44 C49 -178.7(6) . . . . ?
C43 C37 C38 C39 -72.1(6) . . . . ?
C43 C44 C45 N3 5.0(6) . . . . ?
C43 C44 C45 C46 -175.0(5) . . . . ?
C43 C44 C49 C48 174.7(6) . . . . ?
C44 C45 C46 C47 0.6(8) . . . . ?
C45 N3 C42 C41 -173.0(5) . . . . ?
C45 N3 C42 C43 3.3(6) . . . . ?
C45 C44 C49 C48 -0.5(8) . . . . ?
C45 C46 C47 C48 -3.3(9) . . . . ?
C46 C47 C48 C49 4.1(10) . . . . ?
C47 C48 C49 C44 -2.0(9) . . . . ?
C49 C44 C45 N3 -178.7(5) . . . . ?
C49 C44 C45 C46 1.2(8) . . . . ?
C50 S2 N3 C42 -92.4(5) . . . . ?
C50 S2 N3 C45 85.7(5) . . . . ?
C50 C51 C52 C53 -1.6(9) . . . . ?
C51 C50 C56 C55 -1.8(8) . . . . ?
C51 C52 C53 C54 178.2(5) . . . . ?
C51 C52 C53 C55 0.1(8) . . . . ?
C52 C53 C55 C56 0.6(7) . . . . ?
C53 C55 C56 C50 0.2(7) . . . . ?
C54 C53 C55 C56 -177.5(5) . . . . ?
C56 C50 C51 C52 2.5(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and ethyl acetate'
####################################################################### 
# 
# 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_ll-20171007-a
_database_code_depnum_ccdc_archive 'CCDC 1831054'
_audit_update_record             
;
2018-03-20 deposited with the CCDC.
2019-02-01 downloaded from the CCDC.
;
_audit_creation_date             2017-10-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C28 H25 N O4 S'
_chemical_formula_sum            'C28 H25 N O4 S'
_chemical_formula_weight         471.55
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.3488(2)
_cell_length_b                   9.82302(14)
_cell_length_c                   19.2566(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.549(2)
_cell_angle_gamma                90
_cell_volume                     2214.53(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6370
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.5740
_cell_measurement_theta_min      4.8410
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.606
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74423
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41o (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.936
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11619
_diffrn_reflns_point_group_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.583
_diffrn_reflns_theta_min         3.776
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4741
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.936
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     29.00  79.00   1.00   10.00    --   94.84 -30.00   0.00   50
  2  ω     26.00  97.00   1.00   10.00    --   94.84 -45.00 -60.00   71
  3  ω     22.00  89.00   1.00   10.00    --   94.84 -30.00-180.00   67
  4  ω      9.00 177.00   1.00   10.00    --   94.84   0.00-150.00  168
  5  ω    -45.00  30.00   1.00    3.50    --  -40.75  37.00  90.00   75
  6  ω   -115.00 -15.00   1.00    3.50    --  -40.75 -37.00 150.00  100
  7  ω    -79.00 -16.00   1.00    3.50    --  -40.75 -57.00-120.00   63
  8  ω    -42.00  35.00   1.00    3.50    --  -40.75  37.00 -30.00   77
  9  ω     51.00  87.00   1.00    3.50    --   40.75-125.00 -30.00   36
 10  ω     65.00 109.00   1.00   10.00    --  109.81 -94.00  90.00   44
 11  ω     46.00  96.00   1.00   10.00    --  109.81 -45.00  90.00   50
 12  ω     92.00 118.00   1.00   10.00    --  109.81  30.00  30.00   26
 13  ω     60.00 118.00   1.00   10.00    --  109.81-125.00  90.00   58
 14  ω     51.00  94.00   1.00   10.00    --  109.81 -45.00  30.00   43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1229993000
_diffrn_orient_matrix_UB_12      -0.0196684000
_diffrn_orient_matrix_UB_13      -0.0014492000
_diffrn_orient_matrix_UB_21      0.0009477000
_diffrn_orient_matrix_UB_22      0.1476614000
_diffrn_orient_matrix_UB_23      -0.0267768000
_diffrn_orient_matrix_UB_31      0.0466155000
_diffrn_orient_matrix_UB_32      0.0489909000
_diffrn_orient_matrix_UB_33      0.0800394000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3502
_reflns_number_total             3742
_reflns_odcompleteness_completeness 94.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41o (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41o (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41o (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    ?
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         3742
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0479
_refine_ls_restrained_S_all      1.156
_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)+(0.0388P)²+2.7061P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1277
_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:
 C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C18(H18A,H18B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C4(H4), C14(H14), C10(H10), C3(H3), C28(H28), C7(H7), C6(H6),
 C24(H24), C26(H26), C27(H27), C25(H25)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.88064(5) 0.48890(7) 0.34491(4) 0.02879(19) Uani 1 1 d . . . . .
O3 O 0.39353(14) 0.56495(17) 0.16734(10) 0.0291(4) Uani 1 1 d . . . . .
O2 O 0.95722(14) 0.43177(18) 0.41023(10) 0.0306(4) Uani 1 1 d . . . . .
O4 O 0.35479(15) 0.64294(19) 0.26596(11) 0.0350(5) Uani 1 1 d . . . . .
O1 O 0.88869(15) 0.4493(2) 0.27572(10) 0.0357(5) Uani 1 1 d . . . . .
N1 N 0.74905(17) 0.4511(2) 0.34619(12) 0.0278(5) Uani 1 1 d . . . . .
C13 C 0.7212(2) 0.4185(3) 0.41042(15) 0.0280(6) Uani 1 1 d . . . . .
C12 C 0.6021(2) 0.4006(2) 0.38872(14) 0.0272(6) Uani 1 1 d . . . . .
C5 C 0.8892(2) 0.6672(3) 0.35151(14) 0.0293(6) Uani 1 1 d . . . . .
C11 C 0.5501(2) 0.3699(3) 0.44132(15) 0.0296(6) Uani 1 1 d . . . . .
H11 H 0.4699 0.3560 0.4275 0.036 Uiso 1 1 calc R . . . .
C19 C 0.4300(2) 0.4363(2) 0.14212(14) 0.0266(5) Uani 1 1 d . . . . .
C15 C 0.6452(2) 0.4593(3) 0.28610(14) 0.0283(6) Uani 1 1 d . . . . .
C23 C 0.3550(2) 0.4128(3) 0.06365(15) 0.0299(6) Uani 1 1 d . . . . .
C16 C 0.5573(2) 0.4250(3) 0.31100(15) 0.0283(6) Uani 1 1 d . . . . .
C4 C 0.9053(2) 0.7295(3) 0.41887(14) 0.0285(6) Uani 1 1 d . . . . .
H4 H 0.9127 0.6764 0.4614 0.034 Uiso 1 1 calc R . . . .
C22 C 0.3879(2) 0.5521(3) 0.23577(15) 0.0289(6) Uani 1 1 d . . . . .
C20 C 0.5547(2) 0.4496(3) 0.14447(14) 0.0289(6) Uani 1 1 d . . . . .
H20A H 0.5561 0.5032 0.1012 0.035 Uiso 1 1 calc R . . . .
H20B H 0.5832 0.3574 0.1390 0.035 Uiso 1 1 calc R . . . .
C14 C 0.7883(2) 0.4070(3) 0.48323(15) 0.0315(6) Uani 1 1 d . . . . .
H14 H 0.8688 0.4180 0.4971 0.038 Uiso 1 1 calc R . . . .
C9 C 0.7350(2) 0.3790(3) 0.53551(15) 0.0324(6) Uani 1 1 d . . . . .
C10 C 0.6165(2) 0.3602(3) 0.51353(15) 0.0322(6) Uani 1 1 d . . . . .
H10 H 0.5811 0.3402 0.5495 0.039 Uiso 1 1 calc R . . . .
C17 C 0.4328(2) 0.4135(3) 0.26602(15) 0.0290(6) Uani 1 1 d . . . . .
H17 H 0.3874 0.3761 0.2964 0.035 Uiso 1 1 calc R . . . .
C3 C 0.9103(2) 0.8701(3) 0.42304(16) 0.0320(6) Uani 1 1 d . . . . .
H3 H 0.9206 0.9129 0.4689 0.038 Uiso 1 1 calc R . . . .
C18 C 0.4111(2) 0.3310(3) 0.19583(14) 0.0293(6) Uani 1 1 d . . . . .
H18A H 0.3322 0.2949 0.1787 0.035 Uiso 1 1 calc R . . . .
H18B H 0.4657 0.2544 0.2029 0.035 Uiso 1 1 calc R . . . .
C21 C 0.6392(2) 0.5152(3) 0.21246(15) 0.0322(6) Uani 1 1 d . . . . .
H21A H 0.7165 0.5084 0.2076 0.039 Uiso 1 1 calc R . . . .
H21B H 0.6204 0.6132 0.2120 0.039 Uiso 1 1 calc R . . . .
C28 C 0.3402(2) 0.2817(3) 0.03513(16) 0.0354(6) Uani 1 1 d . . . . .
H28 H 0.3776 0.2074 0.0646 0.042 Uiso 1 1 calc R . . . .
C2 C 0.9007(2) 0.9507(3) 0.36170(16) 0.0349(6) Uani 1 1 d . . . . .
C7 C 0.8881(2) 0.8857(3) 0.29579(17) 0.0406(7) Uani 1 1 d . . . . .
H7 H 0.8835 0.9386 0.2536 0.049 Uiso 1 1 calc R . . . .
C6 C 0.8820(2) 0.7451(3) 0.29005(16) 0.0372(7) Uani 1 1 d . . . . .
H6 H 0.8731 0.7022 0.2443 0.045 Uiso 1 1 calc R . . . .
C24 C 0.3022(2) 0.5211(3) 0.01927(16) 0.0363(6) Uani 1 1 d . . . . .
H24 H 0.3136 0.6115 0.0377 0.044 Uiso 1 1 calc R . . . .
C26 C 0.2170(3) 0.3674(4) -0.07922(18) 0.0529(9) Uani 1 1 d . . . . .
H26 H 0.1686 0.3518 -0.1279 0.063 Uiso 1 1 calc R . . . .
C8 C 0.8053(2) 0.3715(4) 0.61543(16) 0.0428(7) Uani 1 1 d . . . . .
H8A H 0.8600 0.2964 0.6229 0.064 Uiso 1 1 calc GR . . . .
H8B H 0.7548 0.3559 0.6450 0.064 Uiso 1 1 calc GR . . . .
H8C H 0.8466 0.4573 0.6303 0.064 Uiso 1 1 calc GR . . . .
C1 C 0.9033(2) 1.1035(3) 0.36727(19) 0.0452(8) Uani 1 1 d . . . . .
H1A H 0.8413 1.1345 0.3850 0.068 Uiso 1 1 calc GR . . . .
H1B H 0.8934 1.1429 0.3189 0.068 Uiso 1 1 calc GR . . . .
H1C H 0.9768 1.1326 0.4015 0.068 Uiso 1 1 calc GR . . . .
C27 C 0.2710(3) 0.2591(4) -0.03625(18) 0.0478(8) Uani 1 1 d . . . . .
H27 H 0.2608 0.1694 -0.0556 0.057 Uiso 1 1 calc R . . . .
C25 C 0.2329(3) 0.4972(4) -0.05189(18) 0.0484(8) Uani 1 1 d . . . . .
H25 H 0.1962 0.5713 -0.0819 0.058 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 O2 1.4264(19) . ?
S1 O1 1.421(2) . ?
S1 N1 1.675(2) . ?
S1 C5 1.756(3) . ?
O3 C19 1.475(3) . ?
O3 C22 1.347(3) . ?
O4 C22 1.205(3) . ?
N1 C13 1.422(3) . ?
N1 C15 1.431(3) . ?
C13 C12 1.406(3) . ?
C13 C14 1.388(4) . ?
C12 C11 1.394(4) . ?
C12 C16 1.441(4) . ?
C5 C4 1.390(4) . ?
C5 C6 1.388(4) . ?
C11 H11 0.9500 . ?
C11 C10 1.375(4) . ?
C19 C23 1.518(4) . ?
C19 C20 1.532(3) . ?
C19 C18 1.532(4) . ?
C15 C16 1.361(4) . ?
C15 C21 1.501(4) . ?
C23 C28 1.389(4) . ?
C23 C24 1.390(4) . ?
C16 C17 1.510(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.384(4) . ?
C22 C17 1.515(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.533(4) . ?
C14 H14 0.9500 . ?
C14 C9 1.394(4) . ?
C9 C10 1.399(4) . ?
C9 C8 1.509(4) . ?
C10 H10 0.9500 . ?
C17 H17 1.0000 . ?
C17 C18 1.525(4) . ?
C3 H3 0.9500 . ?
C3 C2 1.395(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C28 H28 0.9500 . ?
C28 C27 1.386(4) . ?
C2 C7 1.385(4) . ?
C2 C1 1.504(4) . ?
C7 H7 0.9500 . ?
C7 C6 1.386(4) . ?
C6 H6 0.9500 . ?
C24 H24 0.9500 . ?
C24 C25 1.385(4) . ?
C26 H26 0.9500 . ?
C26 C27 1.382(5) . ?
C26 C25 1.369(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C27 H27 0.9500 . ?
C25 H25 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
O2 S1 N1 105.90(11) . . ?
O2 S1 C5 108.71(11) . . ?
O1 S1 O2 119.64(11) . . ?
O1 S1 N1 108.10(11) . . ?
O1 S1 C5 108.65(12) . . ?
N1 S1 C5 104.86(11) . . ?
C22 O3 C19 110.97(19) . . ?
C13 N1 S1 124.57(17) . . ?
C13 N1 C15 108.3(2) . . ?
C15 N1 S1 126.88(18) . . ?
C12 C13 N1 106.8(2) . . ?
C14 C13 N1 131.7(2) . . ?
C14 C13 C12 121.5(2) . . ?
C13 C12 C16 107.9(2) . . ?
C11 C12 C13 119.4(2) . . ?
C11 C12 C16 132.7(2) . . ?
C4 C5 S1 119.6(2) . . ?
C6 C5 S1 120.1(2) . . ?
C6 C5 C4 120.3(3) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 C12 119.1(2) . . ?
C10 C11 H11 120.5 . . ?
O3 C19 C23 107.73(19) . . ?
O3 C19 C20 109.04(19) . . ?
O3 C19 C18 103.20(19) . . ?
C23 C19 C20 109.4(2) . . ?
C23 C19 C18 113.2(2) . . ?
C20 C19 C18 113.9(2) . . ?
N1 C15 C21 123.1(2) . . ?
C16 C15 N1 108.1(2) . . ?
C16 C15 C21 128.3(2) . . ?
C28 C23 C19 119.8(2) . . ?
C28 C23 C24 119.3(3) . . ?
C24 C23 C19 120.9(2) . . ?
C12 C16 C17 124.6(2) . . ?
C15 C16 C12 108.8(2) . . ?
C15 C16 C17 126.6(2) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 H4 120.5 . . ?
O3 C22 C17 109.5(2) . . ?
O4 C22 O3 122.2(2) . . ?
O4 C22 C17 128.2(3) . . ?
C19 C20 H20A 107.9 . . ?
C19 C20 H20B 107.9 . . ?
C19 C20 C21 117.8(2) . . ?
H20A C20 H20B 107.2 . . ?
C21 C20 H20A 107.9 . . ?
C21 C20 H20B 107.9 . . ?
C13 C14 H14 120.7 . . ?
C13 C14 C9 118.6(2) . . ?
C9 C14 H14 120.7 . . ?
C14 C9 C10 119.7(2) . . ?
C14 C9 C8 119.7(2) . . ?
C10 C9 C8 120.6(2) . . ?
C11 C10 C9 121.8(2) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C16 C17 C22 109.6(2) . . ?
C16 C17 H17 110.5 . . ?
C16 C17 C18 114.1(2) . . ?
C22 C17 H17 110.5 . . ?
C22 C17 C18 101.4(2) . . ?
C18 C17 H17 110.5 . . ?
C4 C3 H3 119.1 . . ?
C4 C3 C2 121.8(3) . . ?
C2 C3 H3 119.1 . . ?
C19 C18 H18A 111.2 . . ?
C19 C18 H18B 111.2 . . ?
C17 C18 C19 102.6(2) . . ?
C17 C18 H18A 111.2 . . ?
C17 C18 H18B 111.2 . . ?
H18A C18 H18B 109.2 . . ?
C15 C21 C20 117.9(2) . . ?
C15 C21 H21A 107.8 . . ?
C15 C21 H21B 107.8 . . ?
C20 C21 H21A 107.8 . . ?
C20 C21 H21B 107.8 . . ?
H21A C21 H21B 107.2 . . ?
C23 C28 H28 119.9 . . ?
C27 C28 C23 120.2(3) . . ?
C27 C28 H28 119.9 . . ?
C3 C2 C1 120.8(3) . . ?
C7 C2 C3 118.0(3) . . ?
C7 C2 C1 121.3(3) . . ?
C2 C7 H7 119.3 . . ?
C2 C7 C6 121.4(3) . . ?
C6 C7 H7 119.3 . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.6(3) . . ?
C7 C6 H6 120.2 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 120.0(3) . . ?
C25 C24 H24 120.0 . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C25 C26 C27 120.2(3) . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C28 C27 H27 120.1 . . ?
C26 C27 C28 119.9(3) . . ?
C26 C27 H27 120.1 . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.4(3) . . ?
C26 C25 H25 119.8 . . ?

_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 1.454
_oxdiff_exptl_absorpt_empirical_full_min 0.722
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and ethyl acetate'
