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

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

data_a
_audit_block_doi                 10.5517/ccdc.csd.cc1q5lp5
_database_code_depnum_ccdc_archive 'CCDC 1584307'
_audit_update_record             
;
2017-11-07 deposited with the CCDC.
2018-02-14 downloaded from the CCDC.
;
_audit_creation_date             2017-10-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H23 N2 O S, 2(C H4 O), I'
_chemical_formula_sum            'C21 H27 I N2 O4 S'
_chemical_formula_weight         530.41
_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'
I I -0.3257 6.8362 '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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   7.9761(3)
_cell_length_b                   18.6330(6)
_cell_length_c                   15.9637(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.406(3)
_cell_angle_gamma                90.00
_cell_volume                     2372.44(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6449
_cell_measurement_temperature    150
_cell_measurement_theta_max      61.2120
_cell_measurement_theta_min      3.6750
_exptl_absorpt_coefficient_mu    11.657
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.05658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'metallic grayish gray'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   grayish
_exptl_crystal_colour_primary    gray
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0704
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23391
_diffrn_reflns_theta_full        61.65
_diffrn_reflns_theta_max         61.65
_diffrn_reflns_theta_min         3.65
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3299
_reflns_number_total             3672
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         1.662
_refine_diff_density_min         -0.942
_refine_diff_density_rms         0.176
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         3672
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0583
_refine_ls_restrained_S_all      1.194
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0848P)²+10.8975P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1816
_refine_ls_wR_factor_ref         0.1853
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13), C15(H15)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C33(H33A,H33B,H33C), C21(H21A,H21B,
 H21C), C1(H1A,H1B,H1C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3A), O4(H4A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.1744(3) 0.01573(10) 0.32052(11) 0.0420(5) Uani 1 d . . .
O1 O 0.0945(10) 0.1688(4) 0.5624(4) 0.0638(18) Uani 1 d . . .
N1 N 0.2970(8) -0.1064(3) 0.3590(4) 0.0355(14) Uani 1 d . . .
N2 N 0.2740(8) 0.1336(4) 0.8465(4) 0.0382(14) Uani 1 d . . .
C2 C 0.2618(9) -0.1111(4) 0.2736(5) 0.0355(16) Uani 1 d . . .
C3 C 0.2898(10) -0.1696(4) 0.2214(5) 0.0400(18) Uani 1 d . . .
C4 C 0.2453(11) -0.1628(4) 0.1375(5) 0.0439(19) Uani 1 d . . .
C5 C 0.1735(10) -0.0995(5) 0.1063(5) 0.0437(19) Uani 1 d . . .
C6 C 0.1488(10) -0.0421(5) 0.1582(5) 0.0413(18) Uani 1 d . . .
C7 C 0.1924(9) -0.0478(4) 0.2423(5) 0.0366(16) Uani 1 d . . .
C8 C 0.2572(9) -0.0434(4) 0.3938(5) 0.0358(16) Uani 1 d . . .
C9 C 0.2798(10) -0.0249(4) 0.4793(5) 0.0402(17) Uani 1 d . . .
C10 C 0.2258(10) 0.0376(4) 0.5128(5) 0.0407(17) Uani 1 d . . .
C11 C 0.2399(10) 0.0609(4) 0.5970(5) 0.0395(17) Uani 1 d . . .
C12 C 0.3197(10) 0.0199(4) 0.6607(5) 0.0413(18) Uani 1 d . . .
C13 C 0.3298(10) 0.0430(4) 0.7416(5) 0.0383(17) Uani 1 d . . .
C14 C 0.2629(9) 0.1101(4) 0.7663(4) 0.0357(16) Uani 1 d . . .
C15 C 0.1829(10) 0.1522(4) 0.7036(5) 0.0383(17) Uani 1 d . . .
C16 C 0.1732(10) 0.1271(4) 0.6228(5) 0.0377(17) Uani 1 d . . .
C17 C 0.1936(10) 0.2001(4) 0.8752(5) 0.0404(17) Uani 1 d . . .
C18 C 0.3071(13) 0.2649(5) 0.8695(6) 0.059(2) Uani 1 d . . .
C19 C 0.3691(10) 0.0932(4) 0.9104(5) 0.0405(17) Uani 1 d . . .
C20 C 0.2653(11) 0.0368(5) 0.9546(5) 0.049(2) Uani 1 d . . .
C33 C 0.3712(11) -0.1676(4) 0.4046(5) 0.0419(19) Uani 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0587(12) 0.0367(10) 0.0307(10) -0.0010(7) 0.0041(8) 0.0064(8)
O1 0.097(5) 0.059(4) 0.036(3) -0.003(3) -0.003(3) 0.017(3)
N1 0.043(3) 0.031(3) 0.032(3) 0.002(3) 0.004(3) 0.000(3)
N2 0.047(4) 0.043(4) 0.025(3) 0.002(3) 0.003(3) 0.000(3)
C2 0.038(4) 0.038(4) 0.030(4) 0.001(3) 0.003(3) -0.005(3)
C3 0.047(5) 0.033(4) 0.040(4) 0.001(3) 0.004(3) -0.002(3)
C4 0.053(5) 0.042(5) 0.038(4) -0.010(3) 0.009(4) -0.007(3)
C5 0.052(5) 0.048(5) 0.032(4) -0.001(3) 0.002(3) -0.009(4)
C6 0.046(4) 0.046(5) 0.032(4) 0.003(3) -0.001(3) 0.001(3)
C7 0.041(4) 0.033(4) 0.036(4) -0.004(3) 0.006(3) -0.004(3)
C8 0.043(4) 0.027(4) 0.037(4) 0.003(3) 0.007(3) -0.001(3)
C9 0.048(4) 0.043(4) 0.030(4) 0.000(3) 0.004(3) 0.000(3)
C10 0.045(4) 0.044(5) 0.033(4) -0.001(3) 0.001(3) 0.000(3)
C11 0.045(4) 0.045(5) 0.028(4) 0.000(3) 0.003(3) -0.002(3)
C12 0.041(4) 0.041(4) 0.042(4) -0.001(3) 0.003(3) 0.002(3)
C13 0.044(4) 0.040(4) 0.031(4) 0.002(3) 0.000(3) 0.003(3)
C14 0.042(4) 0.037(4) 0.028(4) 0.000(3) 0.006(3) -0.004(3)
C15 0.049(5) 0.033(4) 0.033(4) 0.002(3) 0.007(3) 0.001(3)
C16 0.050(4) 0.032(4) 0.031(4) 0.001(3) 0.001(3) 0.001(3)
C17 0.046(4) 0.041(4) 0.035(4) -0.003(3) 0.007(3) 0.002(3)
C18 0.069(6) 0.047(5) 0.060(6) -0.010(4) 0.015(5) -0.003(4)
C19 0.053(5) 0.042(4) 0.026(4) -0.001(3) -0.002(3) -0.001(3)
C20 0.054(5) 0.055(5) 0.038(4) 0.014(4) 0.001(4) -0.001(4)
C33 0.058(5) 0.031(4) 0.037(4) 0.003(3) 0.003(4) 0.004(3)

_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 C7 1.727(8) . ?
S1 C8 1.734(8) . ?
O1 C16 1.385(10) . ?
N1 C2 1.393(10) . ?
N1 C8 1.338(10) . ?
N1 C33 1.475(10) . ?
N2 C14 1.356(10) . ?
N2 C17 1.470(10) . ?
N2 C19 1.473(10) . ?
C2 C3 1.391(11) . ?
C2 C7 1.395(11) . ?
C3 C4 1.389(13) . ?
C4 C5 1.400(12) . ?
C5 C6 1.368(12) . ?
C6 C7 1.389(11) . ?
C8 C9 1.419(11) . ?
C9 C10 1.353(12) . ?
C10 C11 1.415(11) . ?
C11 C12 1.419(12) . ?
C11 C16 1.406(11) . ?
C12 C13 1.364(11) . ?
C13 C14 1.416(11) . ?
C14 C15 1.420(11) . ?
C15 C16 1.374(11) . ?
C17 C18 1.513(12) . ?
C19 C20 1.516(12) . ?

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
C7 S1 C8 91.1(4) . . ?
C2 N1 C33 120.8(6) . . ?
C8 N1 C2 114.5(6) . . ?
C8 N1 C33 124.7(6) . . ?
C14 N2 C17 122.7(6) . . ?
C14 N2 C19 121.3(7) . . ?
C17 N2 C19 116.0(6) . . ?
N1 C2 C7 111.9(6) . . ?
C3 C2 N1 127.1(7) . . ?
C3 C2 C7 120.9(7) . . ?
C4 C3 C2 117.7(7) . . ?
C3 C4 C5 121.4(7) . . ?
C6 C5 C4 120.2(8) . . ?
C5 C6 C7 119.3(8) . . ?
C2 C7 S1 110.9(6) . . ?
C6 C7 S1 128.7(6) . . ?
C6 C7 C2 120.4(7) . . ?
N1 C8 S1 111.6(6) . . ?
N1 C8 C9 125.7(7) . . ?
C9 C8 S1 122.7(6) . . ?
C10 C9 C8 123.4(8) . . ?
C9 C10 C11 128.0(8) . . ?
C10 C11 C12 123.2(8) . . ?
C16 C11 C10 121.3(7) . . ?
C16 C11 C12 115.5(7) . . ?
C13 C12 C11 122.1(8) . . ?
C12 C13 C14 121.4(7) . . ?
N2 C14 C13 121.7(7) . . ?
N2 C14 C15 120.9(7) . . ?
C13 C14 C15 117.4(7) . . ?
C16 C15 C14 119.7(7) . . ?
O1 C16 C11 117.3(7) . . ?
C15 C16 O1 119.0(7) . . ?
C15 C16 C11 123.7(7) . . ?
N2 C17 C18 113.1(7) . . ?
N2 C19 C20 113.4(7) . . ?

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 C8 C9 C10 6.0(11) . . . . ?
N1 C2 C3 C4 -179.9(7) . . . . ?
N1 C2 C7 S1 0.3(8) . . . . ?
N1 C2 C7 C6 180.0(7) . . . . ?
N1 C8 C9 C10 -174.8(8) . . . . ?
N2 C14 C15 C16 -179.9(7) . . . . ?
C2 N1 C8 S1 -0.9(8) . . . . ?
C2 N1 C8 C9 179.8(7) . . . . ?
C2 C3 C4 C5 -0.5(12) . . . . ?
C3 C2 C7 S1 -179.3(6) . . . . ?
C3 C2 C7 C6 0.3(11) . . . . ?
C3 C4 C5 C6 1.4(13) . . . . ?
C4 C5 C6 C7 -1.4(12) . . . . ?
C5 C6 C7 S1 -179.9(6) . . . . ?
C5 C6 C7 C2 0.5(12) . . . . ?
C7 S1 C8 N1 0.9(6) . . . . ?
C7 S1 C8 C9 -179.8(7) . . . . ?
C7 C2 C3 C4 -0.3(11) . . . . ?
C8 S1 C7 C2 -0.7(6) . . . . ?
C8 S1 C7 C6 179.7(8) . . . . ?
C8 N1 C2 C3 180.0(7) . . . . ?
C8 N1 C2 C7 0.4(9) . . . . ?
C8 C9 C10 C11 179.2(8) . . . . ?
C9 C10 C11 C12 1.2(14) . . . . ?
C9 C10 C11 C16 -178.3(8) . . . . ?
C10 C11 C12 C13 -179.1(8) . . . . ?
C10 C11 C16 O1 -0.6(12) . . . . ?
C10 C11 C16 C15 179.8(8) . . . . ?
C11 C12 C13 C14 -1.0(12) . . . . ?
C12 C11 C16 O1 179.9(7) . . . . ?
C12 C11 C16 C15 0.3(12) . . . . ?
C12 C13 C14 N2 -179.4(7) . . . . ?
C12 C13 C14 C15 0.7(11) . . . . ?
C13 C14 C15 C16 0.0(11) . . . . ?
C14 N2 C17 C18 -91.8(9) . . . . ?
C14 N2 C19 C20 -88.4(9) . . . . ?
C14 C15 C16 O1 179.9(7) . . . . ?
C14 C15 C16 C11 -0.5(12) . . . . ?
C16 C11 C12 C13 0.5(12) . . . . ?
C17 N2 C14 C13 -174.8(7) . . . . ?
C17 N2 C14 C15 5.1(11) . . . . ?
C17 N2 C19 C20 91.7(8) . . . . ?
C19 N2 C14 C13 5.4(11) . . . . ?
C19 N2 C14 C15 -174.7(7) . . . . ?
C19 N2 C17 C18 88.0(9) . . . . ?
C33 N1 C2 C3 -0.4(11) . . . . ?
C33 N1 C2 C7 180.0(7) . . . . ?
C33 N1 C8 S1 179.5(6) . . . . ?
C33 N1 C8 C9 0.2(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
