# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

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

data_rb31
_database_code_depnum_ccdc_archive 'CCDC 1488802'
_audit_update_record             
;
2016-06-29 deposited with the CCDC.
2016-08-04 downloaded from the CCDC.
;
_audit_creation_date             2016-06-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H21 I N2 O7 S'
_chemical_formula_sum            'C19 H21 I N2 O7 S'
_chemical_formula_weight         548.34
_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'
I I -0.4742 1.8119 '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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   14.1684(3)
_cell_length_b                   6.6657(2)
_cell_length_c                   47.1845(14)
_cell_angle_alpha                90
_cell_angle_beta                 91.503(2)
_cell_angle_gamma                90
_cell_volume                     4454.7(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7075
_cell_measurement_temperature    292.87(11)
_cell_measurement_theta_max      28.7130
_cell_measurement_theta_min      4.1850
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.573
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             2192
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.887
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -65
_diffrn_reflns_number            18178
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.684
_diffrn_reflns_theta_min         3.743
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.87(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.887
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     34.00  74.28   0.38   10.00    --   12.10 -38.00   0.00  106
  2  ω     36.00  62.22   0.38   10.00    --   12.10 -38.00  30.00   69
  3  ω     50.00  83.06   0.38   10.00    --   12.10  77.00 -90.00   87
  4  ω     50.00  77.36   0.38   10.00    --   12.10  77.00 -60.00   72
  5  ω     50.00  80.78   0.38   10.00    --   12.10  77.00-180.00   81
  6  ω    -59.00  28.02   0.38   10.00    --  -12.70 -82.00  30.00  229
  7  ω    -66.00   6.20   0.38   10.00    --   12.10 -38.00  30.00  190
  8  ω    -77.00 -46.60   0.38   10.00    --   12.10 -38.00   0.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0027113000
_diffrn_orient_matrix_UB_12      -0.0055551000
_diffrn_orient_matrix_UB_13      -0.0149662000
_diffrn_orient_matrix_UB_21      0.0487331000
_diffrn_orient_matrix_UB_22      -0.0235635000
_diffrn_orient_matrix_UB_23      0.0013518000
_diffrn_orient_matrix_UB_31      -0.0112157000
_diffrn_orient_matrix_UB_32      -0.1036330000
_diffrn_orient_matrix_UB_33      0.0004982000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4191
_reflns_number_total             5599
_reflns_odcompleteness_completeness 99.17
_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 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7b (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         0.520
_refine_diff_density_min         -0.938
_refine_diff_density_rms         0.203
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         5599
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.061
_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)+(0.0486P)²+2.6402P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1027
_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:
 C3(H3), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16), C18(H18),
 C19(H19)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C6(H6A,H6B,H6C)
;
_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
I1 I 0.50246(2) 0.62365(4) 0.59326(2) 0.07903(11) Uani 1 1 d . . . . .
S1 S 0.27949(4) 1.01991(8) 0.62575(2) 0.04357(14) Uani 1 1 d . . . . .
O1 O 0.22092(11) 0.7500(3) 0.56457(3) 0.0510(4) Uani 1 1 d . . . . .
O2 O 0.4945(2) 0.9089(5) 0.75114(5) 0.1011(9) Uani 1 1 d . . . . .
O3 O 0.61404(17) 0.9408(5) 0.72524(5) 0.1015(9) Uani 1 1 d . . . . .
O4 O 0.3977(2) 0.7098(5) 0.52766(5) 0.0964(8) Uani 1 1 d . . . . .
O5 O 0.36177(17) 0.3890(4) 0.53485(6) 0.0865(8) Uani 1 1 d . . . . .
O6 O 0.32273(16) 1.1570(2) 0.60692(4) 0.0615(5) Uani 1 1 d . . . . .
O7 O 0.18555(13) 1.0581(3) 0.63467(4) 0.0595(5) Uani 1 1 d . . . . .
N1 N 0.28553(12) 0.7955(3) 0.61121(4) 0.0383(4) Uani 1 1 d . . . . .
N2 N 0.53007(19) 0.9342(4) 0.72839(5) 0.0660(6) Uani 1 1 d . . . . .
C1 C 0.0822(3) 0.8853(6) 0.54227(9) 0.0911(12) Uani 1 1 d . . . . .
H1A H 0.0458 0.7872 0.5521 0.137 Uiso 1 1 calc GR . . . .
H1B H 0.0988 0.8336 0.5241 0.137 Uiso 1 1 calc GR . . . .
H1C H 0.0457 1.0056 0.5398 0.137 Uiso 1 1 calc GR . . . .
C2 C 0.1672(2) 0.9298(5) 0.55867(8) 0.0780(9) Uani 1 1 d . . . . .
H2A H 0.2056 1.0235 0.5483 0.094 Uiso 1 1 calc R . . . .
H2B H 0.1506 0.9928 0.5764 0.094 Uiso 1 1 calc R . . . .
C3 C 0.30401(15) 0.7793(4) 0.58074(4) 0.0411(5) Uani 1 1 d . . . . .
H3 H 0.3360 0.9008 0.5743 0.049 Uiso 1 1 calc R . . . .
C4 C 0.36392(18) 0.5964(4) 0.57438(5) 0.0495(6) Uani 1 1 d . . . . .
H4 H 0.3333 0.4757 0.5816 0.059 Uiso 1 1 calc R . . . .
C5 C 0.37647(19) 0.5760(5) 0.54283(7) 0.0636(7) Uani 1 1 d . . . . .
C6 C 0.3754(3) 0.3463(9) 0.50480(11) 0.135(2) Uani 1 1 d . . . . .
H6A H 0.4417 0.3373 0.5013 0.203 Uiso 1 1 calc GR . . . .
H6B H 0.3480 0.4522 0.4935 0.203 Uiso 1 1 calc GR . . . .
H6C H 0.3454 0.2215 0.4999 0.203 Uiso 1 1 calc GR . . . .
C7 C 0.21911(17) 0.6427(3) 0.62217(5) 0.0458(5) Uani 1 1 d . . . . .
H7A H 0.2226 0.5233 0.6105 0.055 Uiso 1 1 calc R . . . .
H7B H 0.1553 0.6945 0.6203 0.055 Uiso 1 1 calc R . . . .
C8 C 0.23837(18) 0.5849(3) 0.65269(5) 0.0470(5) Uani 1 1 d . . . . .
C9 C 0.1651(2) 0.5840(4) 0.67141(7) 0.0660(8) Uani 1 1 d . . . . .
H9 H 0.1043 0.6177 0.6652 0.079 Uiso 1 1 calc R . . . .
C10 C 0.1830(3) 0.5322(6) 0.69961(7) 0.0895(11) Uani 1 1 d . . . . .
H10 H 0.1335 0.5312 0.7122 0.107 Uiso 1 1 calc R . . . .
C11 C 0.2707(3) 0.4836(5) 0.70904(7) 0.0859(11) Uani 1 1 d . . . . .
H11 H 0.2814 0.4510 0.7280 0.103 Uiso 1 1 calc R . . . .
C12 C 0.3438(3) 0.4821(4) 0.69072(6) 0.0699(8) Uani 1 1 d . . . . .
H12 H 0.4043 0.4487 0.6972 0.084 Uiso 1 1 calc R . . . .
C13 C 0.3277(2) 0.5304(4) 0.66247(5) 0.0533(6) Uani 1 1 d . . . . .
H13 H 0.3774 0.5261 0.6500 0.064 Uiso 1 1 calc R . . . .
C14 C 0.35304(15) 1.0020(3) 0.65647(5) 0.0401(5) Uani 1 1 d . . . . .
C15 C 0.31369(16) 0.9974(4) 0.68306(5) 0.0463(5) Uani 1 1 d . . . . .
H15 H 0.2487 1.0081 0.6848 0.056 Uiso 1 1 calc R . . . .
C16 C 0.37137(18) 0.9769(4) 0.70683(5) 0.0500(5) Uani 1 1 d . . . . .
H16 H 0.3461 0.9731 0.7248 0.060 Uiso 1 1 calc R . . . .
C17 C 0.46737(17) 0.9622(4) 0.70335(5) 0.0486(5) Uani 1 1 d . . . . .
C18 C 0.50770(18) 0.9702(5) 0.67710(5) 0.0587(7) Uani 1 1 d . . . . .
H18 H 0.5728 0.9608 0.6754 0.070 Uiso 1 1 calc R . . . .
C19 C 0.44979(17) 0.9923(4) 0.65341(5) 0.0538(6) Uani 1 1 d . . . . .
H19 H 0.4755 1.0007 0.6355 0.065 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
I1 C4 2.142(3) . ?
S1 O6 1.424(2) . ?
S1 O7 1.4294(19) . ?
S1 N1 1.6488(19) . ?
S1 C14 1.767(2) . ?
O1 C2 1.443(3) . ?
O1 C3 1.400(3) . ?
O2 N2 1.209(3) . ?
O3 N2 1.204(3) . ?
O4 C5 1.187(4) . ?
O5 C5 1.317(4) . ?
O5 C6 1.464(5) . ?
N1 C3 1.472(3) . ?
N1 C7 1.489(3) . ?
N2 C17 1.472(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.445(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3 0.9800 . ?
C3 C4 1.520(3) . ?
C4 H4 0.9800 . ?
C4 C5 1.510(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.509(3) . ?
C8 C9 1.381(4) . ?
C8 C13 1.385(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.391(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.348(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.366(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.384(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.387(3) . ?
C14 C19 1.384(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.377(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(3) . ?
C17 C18 1.378(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.377(4) . ?
C19 H19 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
O6 S1 O7 119.24(12) . . ?
O6 S1 N1 107.15(10) . . ?
O6 S1 C14 107.52(12) . . ?
O7 S1 N1 110.07(11) . . ?
O7 S1 C14 107.70(11) . . ?
N1 S1 C14 104.11(10) . . ?
C3 O1 C2 114.9(2) . . ?
C5 O5 C6 115.9(3) . . ?
C3 N1 S1 119.03(15) . . ?
C3 N1 C7 114.79(17) . . ?
C7 N1 S1 115.86(14) . . ?
O2 N2 C17 118.3(3) . . ?
O3 N2 O2 123.4(3) . . ?
O3 N2 C17 118.3(3) . . ?
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 . . ?
O1 C2 C1 111.1(3) . . ?
O1 C2 H2A 109.4 . . ?
O1 C2 H2B 109.4 . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
O1 C3 N1 111.97(17) . . ?
O1 C3 H3 109.7 . . ?
O1 C3 C4 104.27(19) . . ?
N1 C3 H3 109.7 . . ?
N1 C3 C4 111.49(18) . . ?
C4 C3 H3 109.7 . . ?
I1 C4 H4 109.5 . . ?
C3 C4 I1 111.11(16) . . ?
C3 C4 H4 109.5 . . ?
C5 C4 I1 106.70(17) . . ?
C5 C4 C3 110.3(2) . . ?
C5 C4 H4 109.5 . . ?
O4 C5 O5 125.4(3) . . ?
O4 C5 C4 124.4(3) . . ?
O5 C5 C4 110.2(3) . . ?
O5 C6 H6A 109.5 . . ?
O5 C6 H6B 109.5 . . ?
O5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 H7A 108.8 . . ?
N1 C7 H7B 108.8 . . ?
N1 C7 C8 113.95(19) . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
C9 C8 C7 119.4(3) . . ?
C9 C8 C13 118.8(3) . . ?
C13 C8 C7 121.7(2) . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.5(4) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.2(3) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.0(3) . . ?
C13 C12 H12 120.0 . . ?
C8 C13 H13 119.8 . . ?
C12 C13 C8 120.5(3) . . ?
C12 C13 H13 119.8 . . ?
C15 C14 S1 120.09(17) . . ?
C19 C14 S1 118.84(17) . . ?
C19 C14 C15 121.1(2) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.7(2) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 120.8 . . ?
C15 C16 C17 118.4(2) . . ?
C17 C16 H16 120.8 . . ?
C16 C17 N2 119.3(2) . . ?
C16 C17 C18 122.6(2) . . ?
C18 C17 N2 118.1(2) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 C17 118.8(2) . . ?
C19 C18 H18 120.6 . . ?
C14 C19 H19 120.3 . . ?
C18 C19 C14 119.4(2) . . ?
C18 C19 H19 120.3 . . ?

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
I1 C4 C5 O4 -73.9(3) . . . . ?
I1 C4 C5 O5 105.2(2) . . . . ?
S1 N1 C3 O1 -98.5(2) . . . . ?
S1 N1 C3 C4 145.13(17) . . . . ?
S1 N1 C7 C8 -66.2(2) . . . . ?
S1 C14 C15 C16 177.92(19) . . . . ?
S1 C14 C19 C18 -177.4(2) . . . . ?
O1 C3 C4 I1 173.50(14) . . . . ?
O1 C3 C4 C5 55.4(3) . . . . ?
O2 N2 C17 C16 5.8(4) . . . . ?
O2 N2 C17 C18 -173.4(3) . . . . ?
O3 N2 C17 C16 -173.1(3) . . . . ?
O3 N2 C17 C18 7.7(4) . . . . ?
O6 S1 N1 C3 -17.76(19) . . . . ?
O6 S1 N1 C7 -161.06(16) . . . . ?
O6 S1 C14 C15 138.44(19) . . . . ?
O6 S1 C14 C19 -41.7(2) . . . . ?
O7 S1 N1 C3 113.32(16) . . . . ?
O7 S1 N1 C7 -29.98(18) . . . . ?
O7 S1 C14 C15 8.8(2) . . . . ?
O7 S1 C14 C19 -171.4(2) . . . . ?
N1 S1 C14 C15 -108.09(19) . . . . ?
N1 S1 C14 C19 71.8(2) . . . . ?
N1 C3 C4 I1 -65.5(2) . . . . ?
N1 C3 C4 C5 176.3(2) . . . . ?
N1 C7 C8 C9 130.7(2) . . . . ?
N1 C7 C8 C13 -50.0(3) . . . . ?
N2 C17 C18 C19 178.7(3) . . . . ?
C2 O1 C3 N1 80.7(3) . . . . ?
C2 O1 C3 C4 -158.6(2) . . . . ?
C3 O1 C2 C1 -179.2(3) . . . . ?
C3 N1 C7 C8 149.0(2) . . . . ?
C3 C4 C5 O4 46.9(4) . . . . ?
C3 C4 C5 O5 -133.9(2) . . . . ?
C6 O5 C5 O4 1.5(5) . . . . ?
C6 O5 C5 C4 -177.6(3) . . . . ?
C7 N1 C3 O1 45.2(3) . . . . ?
C7 N1 C3 C4 -71.2(2) . . . . ?
C7 C8 C9 C10 -179.5(3) . . . . ?
C7 C8 C13 C12 178.6(2) . . . . ?
C8 C9 C10 C11 0.2(5) . . . . ?
C9 C8 C13 C12 -2.1(4) . . . . ?
C9 C10 C11 C12 -0.8(6) . . . . ?
C10 C11 C12 C13 -0.1(5) . . . . ?
C11 C12 C13 C8 1.5(4) . . . . ?
C13 C8 C9 C10 1.2(4) . . . . ?
C14 S1 N1 C3 -131.49(16) . . . . ?
C14 S1 N1 C7 85.21(17) . . . . ?
C14 C15 C16 C17 0.2(4) . . . . ?
C15 C14 C19 C18 2.5(4) . . . . ?
C15 C16 C17 N2 -178.2(2) . . . . ?
C15 C16 C17 C18 1.0(4) . . . . ?
C16 C17 C18 C19 -0.5(4) . . . . ?
C17 C18 C19 C14 -1.3(4) . . . . ?
C19 C14 C15 C16 -2.0(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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 1.700
_oxdiff_exptl_absorpt_empirical_full_min 0.747
####################################################################### 
# 
# 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_mtbe051_juin2016
_database_code_depnum_ccdc_archive 'CCDC 1488803'
_audit_update_record             
;
2016-06-29 deposited with the CCDC.
2016-08-04 downloaded from the CCDC.
;
_audit_creation_date             2016-06-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H21 I N2 O6 S'
_chemical_formula_sum            'C18 H21 I N2 O6 S'
_chemical_formula_weight         520.33
_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'
I I -0.4742 1.8119 '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                   6.7507(4)
_cell_length_b                   14.1829(7)
_cell_length_c                   43.847(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4198.1(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5883
_cell_measurement_temperature    292.8(2)
_cell_measurement_theta_max      26.8810
_cell_measurement_theta_min      3.5150
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.661
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59437
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2080
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            19785
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.718
_diffrn_reflns_theta_min         3.374
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.8(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  84.86   0.38   60.00    --   12.50  19.00-120.00  247
  2  ω    -76.00 -22.80   0.38   60.00    --   12.50  19.00-120.00  140
  3  ω     -1.00  24.46   0.38   60.00    --  -12.90 -77.00  60.00   67
  4  ω    -60.00 -28.08   0.38   60.00    --  -12.90 -77.00  60.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0711964000
_diffrn_orient_matrix_UB_12      -0.0352658000
_diffrn_orient_matrix_UB_13      0.0033853000
_diffrn_orient_matrix_UB_21      0.0187260000
_diffrn_orient_matrix_UB_22      -0.0059230000
_diffrn_orient_matrix_UB_23      -0.0158013000
_diffrn_orient_matrix_UB_31      0.0750048000
_diffrn_orient_matrix_UB_32      0.0349451000
_diffrn_orient_matrix_UB_33      0.0007342000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3243
_reflns_number_total             5384
_reflns_odcompleteness_completeness 99.37
_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 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7b (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         0.732
_refine_diff_density_min         -1.061
_refine_diff_density_rms         0.166
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         5384
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1043
_refine_ls_R_factor_gt           0.0597
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0823P)²+4.6521P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1650
_refine_ls_wR_factor_ref         0.1827
_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, All O(H) groups
2. Others
 Sof(O5)=Sof(H5)=Sof(H4B)=Sof(C5)=Sof(H5A)=Sof(H5B)=1-FVAR(1)
 Sof(O4)=Sof(H4)=Sof(H4A)=Sof(C6)=Sof(H6A)=Sof(H6B)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4A), C4(H4B)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
3.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16), C18(H18),
 C19(H19)
3.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
3.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5)
;
_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
I1 I 0.61557(7) 0.23312(3) 0.66912(2) 0.0813(2) Uani 1 1 d . . . . .
S1 S 0.23241(16) 0.45894(8) 0.63322(3) 0.0436(3) Uani 1 1 d . . . . .
O1 O 0.4954(5) 0.5125(2) 0.69962(7) 0.0483(8) Uani 1 1 d . . . . .
O2 O 0.3528(9) 0.2548(4) 0.49854(11) 0.105(2) Uani 1 1 d . . . . .
O3 O 0.3128(10) 0.1331(3) 0.52614(10) 0.1050(18) Uani 1 1 d . . . . .
O4 O 0.765(2) 0.4317(10) 0.7370(3) 0.104(6) Uani 0.52(2) 1 d . . P A 1
H4 H 0.8508 0.4545 0.7260 0.157 Uiso 0.52(2) 1 calc GR . P A 1
O5 O 0.620(3) 0.3531(14) 0.7397(4) 0.135(10) Uani 0.48(2) 1 d . . P A 2
H5 H 0.5666 0.3975 0.7484 0.203 Uiso 0.48(2) 1 calc GR . P A 2
O6 O 0.1896(6) 0.5525(2) 0.62355(8) 0.0617(9) Uani 1 1 d . . . . .
O7 O 0.1004(4) 0.4124(3) 0.65386(8) 0.0578(9) Uani 1 1 d . . . . .
N1 N 0.4531(5) 0.4550(2) 0.64891(8) 0.0391(8) Uani 1 1 d . . . . .
N2 N 0.3203(8) 0.2168(4) 0.52308(11) 0.0685(13) Uani 1 1 d . . . . .
C1 C 0.3612(10) 0.6450(5) 0.72479(16) 0.0805(19) Uani 1 1 d . . . . .
H1A H 0.4678 0.6832 0.7172 0.121 Uiso 1 1 calc GR . . . .
H1B H 0.3977 0.6185 0.7441 0.121 Uiso 1 1 calc GR . . . .
H1C H 0.2449 0.6832 0.7272 0.121 Uiso 1 1 calc GR . . . .
C2 C 0.3207(8) 0.5699(4) 0.70338(12) 0.0580(13) Uani 1 1 d . . . . .
H2A H 0.2123 0.5314 0.7109 0.070 Uiso 1 1 calc R . . . .
H2B H 0.2819 0.5963 0.6839 0.070 Uiso 1 1 calc R . . . .
C3 C 0.4748(7) 0.4314(3) 0.68123(9) 0.0396(9) Uani 1 1 d . . . . .
H3 H 0.3575 0.3963 0.6879 0.048 Uiso 1 1 calc R . . . .
C4 C 0.6582(8) 0.3717(4) 0.68720(11) 0.0536(12) Uani 1 1 d . . . . .
H4A H 0.7781 0.4014 0.6790 0.064 Uiso 0.52(2) 1 calc R . P A 1
H4B H 0.7579 0.3992 0.6736 0.064 Uiso 0.48(2) 1 calc R . P A 2
C5 C 0.751(4) 0.385(2) 0.7198(6) 0.082(8) Uani 0.48(2) 1 d . . P A 2
H5A H 0.8740 0.3508 0.7215 0.098 Uiso 0.48(2) 1 calc R . P A 2
H5B H 0.7771 0.4517 0.7236 0.098 Uiso 0.48(2) 1 calc R . P A 2
C6 C 0.681(3) 0.3478(14) 0.7221(5) 0.062(5) Uani 0.52(2) 1 d . . P A 1
H6A H 0.5527 0.3327 0.7309 0.075 Uiso 0.52(2) 1 calc R . P A 1
H6B H 0.7678 0.2941 0.7248 0.075 Uiso 0.52(2) 1 calc R . P A 1
C7 C 0.6019(7) 0.5235(4) 0.63684(11) 0.0511(12) Uani 1 1 d . . . . .
H7A H 0.7191 0.5211 0.6496 0.061 Uiso 1 1 calc R . . . .
H7B H 0.5474 0.5866 0.6384 0.061 Uiso 1 1 calc R . . . .
C8 C 0.6624(7) 0.5060(4) 0.60433(10) 0.0454(11) Uani 1 1 d . . . . .
C9 C 0.7220(7) 0.4176(4) 0.59470(11) 0.0527(12) Uani 1 1 d . . . . .
H9 H 0.7264 0.3679 0.6085 0.063 Uiso 1 1 calc R . . . .
C10 C 0.7753(8) 0.4029(5) 0.56444(13) 0.0700(16) Uani 1 1 d . . . . .
H10 H 0.8106 0.3427 0.5580 0.084 Uiso 1 1 calc R . . . .
C11 C 0.7764(10) 0.4747(7) 0.54447(14) 0.088(2) Uani 1 1 d . . . . .
H11 H 0.8134 0.4641 0.5243 0.105 Uiso 1 1 calc R . . . .
C12 C 0.7231(12) 0.5640(7) 0.55373(14) 0.092(2) Uani 1 1 d . . . . .
H12 H 0.7257 0.6138 0.5399 0.110 Uiso 1 1 calc R . . . .
C13 C 0.6644(9) 0.5797(5) 0.58423(13) 0.0702(16) Uani 1 1 d . . . . .
H13 H 0.6274 0.6397 0.5906 0.084 Uiso 1 1 calc R . . . .
C14 C 0.2514(7) 0.3878(3) 0.60009(9) 0.0411(10) Uani 1 1 d . . . . .
C15 C 0.2609(9) 0.2912(3) 0.60328(11) 0.0559(13) Uani 1 1 d . . . . .
H15 H 0.2512 0.2640 0.6225 0.067 Uiso 1 1 calc R . . . .
C16 C 0.2844(10) 0.2351(4) 0.57808(11) 0.0619(15) Uani 1 1 d . . . . .
H16 H 0.2940 0.1700 0.5799 0.074 Uiso 1 1 calc R . . . .
C17 C 0.2936(8) 0.2782(3) 0.54985(11) 0.0494(11) Uani 1 1 d . . . . .
C18 C 0.2800(7) 0.3736(4) 0.54606(11) 0.0505(12) Uani 1 1 d . . . . .
H18 H 0.2851 0.4003 0.5267 0.061 Uiso 1 1 calc R . . . .
C19 C 0.2583(7) 0.4297(3) 0.57176(10) 0.0465(10) Uani 1 1 d . . . . .
H19 H 0.2485 0.4948 0.5699 0.056 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
I1 C4 2.139(5) . ?
S1 O6 1.422(4) . ?
S1 O7 1.431(4) . ?
S1 N1 1.642(4) . ?
S1 C14 1.774(4) . ?
O1 C2 1.442(6) . ?
O1 C3 1.412(5) . ?
O2 N2 1.224(7) . ?
O3 N2 1.196(6) . ?
O4 H4 0.8200 . ?
O4 C6 1.47(3) . ?
O5 H5 0.8200 . ?
O5 C5 1.32(4) . ?
N1 C3 1.463(6) . ?
N1 C7 1.495(6) . ?
N2 C17 1.473(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.446(8) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3 0.9800 . ?
C3 C4 1.523(7) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 C5 1.57(3) . ?
C4 C6 1.57(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.504(7) . ?
C8 C9 1.383(7) . ?
C8 C13 1.367(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.391(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.343(10) . ?
C11 H11 0.9300 . ?
C11 C12 1.377(11) . ?
C12 H12 0.9300 . ?
C12 C13 1.413(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.379(7) . ?
C14 C19 1.378(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.370(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(7) . ?
C17 C18 1.365(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.387(7) . ?
C19 H19 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
O6 S1 O7 119.5(2) . . ?
O6 S1 N1 110.0(2) . . ?
O6 S1 C14 107.5(2) . . ?
O7 S1 N1 106.49(19) . . ?
O7 S1 C14 107.5(2) . . ?
N1 S1 C14 105.0(2) . . ?
C3 O1 C2 116.4(4) . . ?
C6 O4 H4 109.5 . . ?
C5 O5 H5 109.5 . . ?
C3 N1 S1 120.3(3) . . ?
C3 N1 C7 115.1(3) . . ?
C7 N1 S1 116.1(3) . . ?
O2 N2 C17 117.5(5) . . ?
O3 N2 O2 123.0(5) . . ?
O3 N2 C17 119.5(5) . . ?
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 . . ?
O1 C2 C1 109.6(5) . . ?
O1 C2 H2A 109.8 . . ?
O1 C2 H2B 109.8 . . ?
C1 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
O1 C3 N1 112.2(3) . . ?
O1 C3 H3 108.9 . . ?
O1 C3 C4 105.9(4) . . ?
N1 C3 H3 108.9 . . ?
N1 C3 C4 112.0(4) . . ?
C4 C3 H3 108.9 . . ?
I1 C4 H4A 111.7 . . ?
I1 C4 H4B 103.4 . . ?
C3 C4 I1 109.7(3) . . ?
C3 C4 H4A 111.7 . . ?
C3 C4 H4B 103.4 . . ?
C3 C4 C5 114.2(10) . . ?
C3 C4 C6 111.4(9) . . ?
C5 C4 I1 120.3(10) . . ?
C5 C4 H4B 103.4 . . ?
C6 C4 I1 100.1(8) . . ?
C6 C4 H4A 111.7 . . ?
O5 C5 C4 107(2) . . ?
O5 C5 H5A 110.3 . . ?
O5 C5 H5B 110.3 . . ?
C4 C5 H5A 110.3 . . ?
C4 C5 H5B 110.3 . . ?
H5A C5 H5B 108.6 . . ?
O4 C6 C4 107.0(16) . . ?
O4 C6 H6A 110.3 . . ?
O4 C6 H6B 110.3 . . ?
C4 C6 H6A 110.3 . . ?
C4 C6 H6B 110.3 . . ?
H6A C6 H6B 108.6 . . ?
N1 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
N1 C7 C8 114.2(4) . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C9 C8 C7 121.2(4) . . ?
C13 C8 C7 119.2(5) . . ?
C13 C8 C9 119.6(5) . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.2(5) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.6(6) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.2(6) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.8(7) . . ?
C13 C12 H12 120.1 . . ?
C8 C13 C12 119.5(7) . . ?
C8 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C15 C14 S1 119.1(3) . . ?
C19 C14 S1 119.7(3) . . ?
C19 C14 C15 121.2(4) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0(4) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 121.0 . . ?
C15 C16 C17 118.1(5) . . ?
C17 C16 H16 121.0 . . ?
C16 C17 N2 117.2(5) . . ?
C18 C17 N2 119.8(5) . . ?
C18 C17 C16 123.0(5) . . ?
C17 C18 H18 120.8 . . ?
C17 C18 C19 118.4(4) . . ?
C19 C18 H18 120.8 . . ?
C14 C19 C18 119.2(4) . . ?
C14 C19 H19 120.4 . . ?
C18 C19 H19 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
I1 C4 C5 O5 -67.8(18) . . . . ?
I1 C4 C6 O4 164.8(12) . . . . ?
S1 N1 C3 O1 -97.9(4) . . . . ?
S1 N1 C3 C4 143.1(4) . . . . ?
S1 N1 C7 C8 -66.6(5) . . . . ?
S1 C14 C15 C16 -177.1(5) . . . . ?
S1 C14 C19 C18 177.8(4) . . . . ?
O1 C3 C4 I1 166.8(3) . . . . ?
O1 C3 C4 C5 28.3(15) . . . . ?
O1 C3 C4 C6 56.9(10) . . . . ?
O2 N2 C17 C16 -171.3(6) . . . . ?
O2 N2 C17 C18 8.4(8) . . . . ?
O3 N2 C17 C16 7.6(9) . . . . ?
O3 N2 C17 C18 -172.7(6) . . . . ?
O6 S1 N1 C3 115.5(3) . . . . ?
O6 S1 N1 C7 -30.8(4) . . . . ?
O6 S1 C14 C15 -169.7(4) . . . . ?
O6 S1 C14 C19 10.8(4) . . . . ?
O7 S1 N1 C3 -15.3(4) . . . . ?
O7 S1 N1 C7 -161.6(3) . . . . ?
O7 S1 C14 C15 -39.9(5) . . . . ?
O7 S1 C14 C19 140.7(4) . . . . ?
N1 S1 C14 C15 73.2(4) . . . . ?
N1 S1 C14 C19 -106.2(4) . . . . ?
N1 C3 C4 I1 -70.6(4) . . . . ?
N1 C3 C4 C5 150.9(14) . . . . ?
N1 C3 C4 C6 179.5(9) . . . . ?
N1 C7 C8 C9 -50.2(6) . . . . ?
N1 C7 C8 C13 131.9(5) . . . . ?
N2 C17 C18 C19 -178.9(5) . . . . ?
C2 O1 C3 N1 71.2(5) . . . . ?
C2 O1 C3 C4 -166.3(4) . . . . ?
C3 O1 C2 C1 175.1(5) . . . . ?
C3 N1 C7 C8 145.4(4) . . . . ?
C3 C4 C5 O5 66(2) . . . . ?
C3 C4 C6 O4 -79.2(16) . . . . ?
C7 N1 C3 O1 48.7(5) . . . . ?
C7 N1 C3 C4 -70.3(5) . . . . ?
C7 C8 C9 C10 179.4(4) . . . . ?
C7 C8 C13 C12 179.3(5) . . . . ?
C8 C9 C10 C11 2.4(8) . . . . ?
C9 C8 C13 C12 1.4(8) . . . . ?
C9 C10 C11 C12 -0.5(10) . . . . ?
C10 C11 C12 C13 -0.9(11) . . . . ?
C11 C12 C13 C8 0.4(10) . . . . ?
C13 C8 C9 C10 -2.8(7) . . . . ?
C14 S1 N1 C3 -129.1(3) . . . . ?
C14 S1 N1 C7 84.6(3) . . . . ?
C14 C15 C16 C17 -1.4(9) . . . . ?
C15 C14 C19 C18 -1.6(7) . . . . ?
C15 C16 C17 N2 179.6(5) . . . . ?
C15 C16 C17 C18 -0.1(9) . . . . ?
C16 C17 C18 C19 0.8(8) . . . . ?
C17 C18 C19 C14 0.1(7) . . . . ?
C19 C14 C15 C16 2.3(8) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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 1.412
_oxdiff_exptl_absorpt_empirical_full_min 0.774
