# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_HDb_a
_database_code_depnum_ccdc_archive 'CCDC 1512675'
_audit_update_record             
;
2016-10-28 deposited with the CCDC.
2016-11-23 downloaded from the CCDC.
;
_audit_creation_date             2016-10-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_shelxl_version_number           2014-3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'I, C16.87 H15.62 N O S'
_chemical_formula_sum            'C17.05 H16.14 I N O S'
_chemical_formula_weight         409.98
_chemical_melting_point          ?
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_diffrn_ambient_temperature      293(2)
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           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                   7.4292(2)
_cell_length_b                   10.7679(2)
_cell_length_c                   20.5682(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.0000(10)
_cell_angle_gamma                90
_cell_volume                     1645.39(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.071
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             810
_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  0.0302
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            27295
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.094
_diffrn_reflns_theta_min         1.980
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3254
_reflns_number_total             4401
_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       ?
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.994
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.0000(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         4401
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0311
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          8.086
_refine_ls_shift/su_mean         0.042
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0414P)²+0.6928P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0860
_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. Uiso/Uaniso restraints and constraints
Uanis(C0AA) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
3. Others
 Sof(C0AA)=Sof(H0AA)=Sof(H0AB)=Sof(H0AC)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
4.b Aromatic/amide H refined with riding coordinates:
 C5BA(H5BA), C2AA(H2AA), C5AA(H5AA), C6AA(H6AA), C3AA(H3AA), C2BA(H2BA),
 C3BA(H3BA), C9AA(H9AA), C0BA(H0BA), C1BA(H1BA)
4.c Idealised Me refined as rotating group:
 C0AA(H0AA,H0AB,H0AC)
4.d Idealised tetrahedral OH refined as rotating group:
 O(H)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I I 0.39572(3) 0.34184(2) 0.60801(2) 0.06975(11) Uani 1 1 d . . . . .
S1AA S 0.83059(10) -0.01097(6) 0.37463(3) 0.04947(16) Uani 1 1 d . . . . .
N3AA N 0.7615(3) 0.20487(18) 0.41787(10) 0.0418(4) Uani 1 1 d . . . . .
C4AA C 0.7721(3) 0.0873(2) 0.43695(11) 0.0419(5) Uani 1 1 d . . . . .
C5BA C 0.6614(3) -0.0714(2) 0.63628(12) 0.0472(5) Uani 1 1 d . . . . .
H5BA H 0.6449 0.0142 0.6344 0.057 Uiso 1 1 calc R . . . .
C1AA C 0.8009(3) 0.2237(2) 0.35206(12) 0.0412(5) Uani 1 1 d . . . . .
C2AA C 0.6371(4) -0.1324(2) 0.69448(13) 0.0494(6) Uani 1 1 d . . . . .
H2AA H 0.6049 -0.0883 0.7316 0.059 Uiso 1 1 calc R . . . .
C5AA C 0.7375(3) 0.0438(2) 0.50192(12) 0.0468(6) Uani 1 1 d . . . . .
H5AA H 0.7108 0.1013 0.5342 0.056 Uiso 1 1 calc R . . . .
C6AA C 0.7426(3) -0.0769(2) 0.51731(11) 0.0446(5) Uani 1 1 d . . . . .
H6AA H 0.7705 -0.1305 0.4833 0.054 Uiso 1 1 calc R . . . .
C3AA C 0.7032(4) -0.3265(2) 0.64201(14) 0.0541(6) Uani 1 1 d . . . . .
H3AA H 0.7155 -0.4124 0.6437 0.065 Uiso 1 1 calc R . . . .
C2BA C 0.8794(4) 0.1092(3) 0.25489(13) 0.0572(7) Uani 1 1 d . . . . .
H2BA H 0.9052 0.0347 0.2340 0.069 Uiso 1 1 calc R . . . .
C3BA C 0.8002(4) 0.3350(2) 0.31774(15) 0.0543(6) Uani 1 1 d . . . . .
H3BA H 0.7740 0.4098 0.3382 0.065 Uiso 1 1 calc R . . . .
C4BA C 0.7105(3) -0.1356(2) 0.57988(11) 0.0422(5) Uani 1 1 d . . . . .
C7AA C 0.6611(3) -0.2607(2) 0.69747(12) 0.0463(5) Uani 1 1 d . . . . .
C8AA C 0.8412(3) 0.1130(2) 0.32072(12) 0.0430(5) Uani 1 1 d . . . . .
C9AA C 0.7270(4) -0.2641(2) 0.58402(12) 0.0493(6) Uani 1 1 d . . . . .
H9AA H 0.7547 -0.3091 0.5468 0.059 Uiso 1 1 calc R . . . .
C0AA C 0.8581(5) 0.3641(4) 0.4983(2) 0.0762(14) Uani 0.873(8) 1 d . U P A 1
H0AA H 0.9167 0.3007 0.5234 0.114 Uiso 0.873(8) 1 calc GR . P A 1
H0AB H 0.8125 0.4272 0.5269 0.114 Uiso 0.873(8) 1 calc GR . P A 1
H0AC H 0.9428 0.4003 0.4686 0.114 Uiso 0.873(8) 1 calc GR . P A 1
C0BA C 0.8777(4) 0.2206(3) 0.22161(14) 0.0641(7) Uani 1 1 d . . . . .
H0BA H 0.9029 0.2214 0.1773 0.077 Uiso 1 1 calc R . . . .
C1BA C 0.8393(4) 0.3303(3) 0.25302(16) 0.0618(7) Uani 1 1 d . . . . .
H1BA H 0.8401 0.4038 0.2293 0.074 Uiso 1 1 calc R . . . .
O O 0.6423(4) -0.32686(18) 0.75299(10) 0.0662(6) Uani 1 1 d . . . . .
H H 0.6188 -0.2797 0.7831 0.099 Uiso 1 1 calc GR . . . .
C3 C 0.7054(4) 0.3080(2) 0.46086(14) 0.0533(6) Uani 1 1 d . . . . .
H3A H 0.6160 0.2774 0.4913 0.064 Uiso 1 1 calc R . . A .
H3B H 0.6492 0.3721 0.4347 0.064 Uiso 1 1 calc R . . A .


_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
S1AA C4AA 1.718(2) . ?
S1AA C8AA 1.737(2) . ?
N3AA C4AA 1.328(3) . ?
N3AA C1AA 1.400(3) . ?
N3AA C3 1.480(3) . ?
C4AA C5AA 1.439(3) . ?
C5BA H5BA 0.9300 . ?
C5BA C2AA 1.377(4) . ?
C5BA C4BA 1.399(3) . ?
C1AA C3BA 1.391(3) . ?
C1AA C8AA 1.388(3) . ?
C2AA H2AA 0.9300 . ?
C2AA C7AA 1.395(4) . ?
C5AA H5AA 0.9300 . ?
C5AA C6AA 1.338(4) . ?
C6AA H6AA 0.9300 . ?
C6AA C4BA 1.454(3) . ?
C3AA H3AA 0.9300 . ?
C3AA C7AA 1.379(4) . ?
C3AA C9AA 1.380(4) . ?
C2BA H2BA 0.9300 . ?
C2BA C8AA 1.384(3) . ?
C2BA C0BA 1.381(4) . ?
C3BA H3BA 0.9300 . ?
C3BA C1BA 1.363(4) . ?
C4BA C9AA 1.391(3) . ?
C7AA O 1.353(3) . ?
C9AA H9AA 0.9300 . ?
C0AA H0AA 0.9600 . ?
C0AA H0AB 0.9600 . ?
C0AA H0AC 0.9600 . ?
C0AA C3 1.498(4) . ?
C0BA H0BA 0.9300 . ?
C0BA C1BA 1.377(4) . ?
C1BA H1BA 0.9300 . ?
O H 0.8200 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?

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
C4AA S1AA C8AA 90.84(12) . . ?
C4AA N3AA C1AA 114.3(2) . . ?
C4AA N3AA C3 123.8(2) . . ?
C1AA N3AA C3 121.9(2) . . ?
N3AA C4AA S1AA 112.43(17) . . ?
N3AA C4AA C5AA 125.0(2) . . ?
C5AA C4AA S1AA 122.53(19) . . ?
C2AA C5BA H5BA 119.4 . . ?
C2AA C5BA C4BA 121.3(2) . . ?
C4BA C5BA H5BA 119.4 . . ?
C3BA C1AA N3AA 128.0(2) . . ?
C8AA C1AA N3AA 111.7(2) . . ?
C8AA C1AA C3BA 120.3(2) . . ?
C5BA C2AA H2AA 120.2 . . ?
C5BA C2AA C7AA 119.6(2) . . ?
C7AA C2AA H2AA 120.2 . . ?
C4AA C5AA H5AA 119.0 . . ?
C6AA C5AA C4AA 122.0(2) . . ?
C6AA C5AA H5AA 119.0 . . ?
C5AA C6AA H6AA 115.6 . . ?
C5AA C6AA C4BA 128.9(2) . . ?
C4BA C6AA H6AA 115.6 . . ?
C7AA C3AA H3AA 120.2 . . ?
C7AA C3AA C9AA 119.6(2) . . ?
C9AA C3AA H3AA 120.2 . . ?
C8AA C2BA H2BA 121.4 . . ?
C0BA C2BA H2BA 121.4 . . ?
C0BA C2BA C8AA 117.2(3) . . ?
C1AA C3BA H3BA 121.2 . . ?
C1BA C3BA C1AA 117.6(3) . . ?
C1BA C3BA H3BA 121.2 . . ?
C5BA C4BA C6AA 124.2(2) . . ?
C9AA C4BA C5BA 117.6(2) . . ?
C9AA C4BA C6AA 118.2(2) . . ?
C3AA C7AA C2AA 120.1(2) . . ?
O C7AA C2AA 123.1(2) . . ?
O C7AA C3AA 116.8(2) . . ?
C1AA C8AA S1AA 110.72(18) . . ?
C2BA C8AA S1AA 127.7(2) . . ?
C2BA C8AA C1AA 121.6(2) . . ?
C3AA C9AA C4BA 121.7(2) . . ?
C3AA C9AA H9AA 119.1 . . ?
C4BA C9AA H9AA 119.1 . . ?
H0AA C0AA H0AB 109.5 . . ?
H0AA C0AA H0AC 109.5 . . ?
H0AB C0AA H0AC 109.5 . . ?
C3 C0AA H0AA 109.5 . . ?
C3 C0AA H0AB 109.5 . . ?
C3 C0AA H0AC 109.5 . . ?
C2BA C0BA H0BA 119.5 . . ?
C1BA C0BA C2BA 121.0(3) . . ?
C1BA C0BA H0BA 119.5 . . ?
C3BA C1BA C0BA 122.3(3) . . ?
C3BA C1BA H1BA 118.9 . . ?
C0BA C1BA H1BA 118.9 . . ?
C7AA O H 109.5 . . ?
N3AA C3 C0AA 113.3(2) . . ?
N3AA C3 H3A 108.9 . . ?
N3AA C3 H3B 108.9 . . ?
C0AA C3 H3A 108.9 . . ?
C0AA C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?

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
S1AA C4AA C5AA C6AA -2.4(3) . . . . ?
N3AA C4AA C5AA C6AA 176.9(2) . . . . ?
N3AA C1AA C3BA C1BA -178.5(3) . . . . ?
N3AA C1AA C8AA S1AA -0.5(3) . . . . ?
N3AA C1AA C8AA C2BA 178.2(2) . . . . ?
C4AA S1AA C8AA C1AA 0.27(19) . . . . ?
C4AA S1AA C8AA C2BA -178.4(3) . . . . ?
C4AA N3AA C1AA C3BA 179.5(2) . . . . ?
C4AA N3AA C1AA C8AA 0.6(3) . . . . ?
C4AA N3AA C3 C0AA 87.6(3) . . . . ?
C4AA C5AA C6AA C4BA -179.7(2) . . . . ?
C5BA C2AA C7AA C3AA -2.1(4) . . . . ?
C5BA C2AA C7AA O 179.0(3) . . . . ?
C5BA C4BA C9AA C3AA -2.6(4) . . . . ?
C1AA N3AA C4AA S1AA -0.4(3) . . . . ?
C1AA N3AA C4AA C5AA -179.8(2) . . . . ?
C1AA N3AA C3 C0AA -95.2(3) . . . . ?
C1AA C3BA C1BA C0BA 0.3(5) . . . . ?
C2AA C5BA C4BA C6AA -178.5(2) . . . . ?
C2AA C5BA C4BA C9AA 2.5(4) . . . . ?
C5AA C6AA C4BA C5BA 2.1(4) . . . . ?
C5AA C6AA C4BA C9AA -178.9(3) . . . . ?
C6AA C4BA C9AA C3AA 178.3(2) . . . . ?
C2BA C0BA C1BA C3BA -0.5(5) . . . . ?
C3BA C1AA C8AA S1AA -179.5(2) . . . . ?
C3BA C1AA C8AA C2BA -0.8(4) . . . . ?
C4BA C5BA C2AA C7AA -0.2(4) . . . . ?
C7AA C3AA C9AA C4BA 0.4(4) . . . . ?
C8AA S1AA C4AA N3AA 0.08(19) . . . . ?
C8AA S1AA C4AA C5AA 179.5(2) . . . . ?
C8AA C1AA C3BA C1BA 0.3(4) . . . . ?
C8AA C2BA C0BA C1BA 0.0(5) . . . . ?
C9AA C3AA C7AA C2AA 2.0(4) . . . . ?
C9AA C3AA C7AA O -179.0(3) . . . . ?
C0BA C2BA C8AA S1AA 179.1(2) . . . . ?
C0BA C2BA C8AA C1AA 0.6(4) . . . . ?
C3 N3AA C4AA S1AA 176.99(18) . . . . ?
C3 N3AA C4AA C5AA -2.4(4) . . . . ?
C3 N3AA C1AA C3BA 2.1(4) . . . . ?
C3 N3AA C1AA C8AA -176.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_symmetry_cell_setting           ?
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_HDa_a
_database_code_depnum_ccdc_archive 'CCDC 1512676'
_audit_update_record             
;
2016-10-28 deposited with the CCDC.
2016-11-23 downloaded from the CCDC.
;
_audit_creation_date             2016-10-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'I, C18 H18 N O S'
_chemical_formula_sum            'C18 H18 I N O S'
_chemical_formula_weight         423.29
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7022(8)
_cell_length_b                   10.3394(11)
_cell_length_c                   11.3339(12)
_cell_angle_alpha                97.090(4)
_cell_angle_beta                 99.284(4)
_cell_angle_gamma                91.950(4)
_cell_volume                     882.61(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.933
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             420
_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  0.0284
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            37226
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.614
_diffrn_reflns_theta_min         1.836
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4776
_reflns_number_total             5427
_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       ?
_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    'XM (Sheldrick, 2008)'
_refine_diff_density_max         0.943
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.182
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         5427
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0225
_refine_ls_restrained_S_all      1.182
_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)+(0.0431P)²+0.1170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0610
_refine_ls_wR_factor_ref         0.0774
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C010(H01A,H01B)
2.b Aromatic/amide H refined with riding coordinates:
 C005(H005), C007(H007), C011(H011), C012(H012), C013(H013), C015(H015),
 C016(H016), C018(H018), C019(H019), C1(H1)
2.c Idealised Me refined as rotating group:
 C020(H02A,H02B,H02C), C(HA,HB,HC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I001 I 0.14678(2) 0.34567(2) 0.21513(2) 0.04590(6) Uani 1 1 d . . . . .
S002 S -0.44202(6) -0.01580(5) -0.22542(4) 0.03793(10) Uani 1 1 d . . . . .
N1 N -0.34132(19) 0.21721(15) -0.13223(14) 0.0343(3) Uani 1 1 d . . . . .
C005 C -0.2269(2) -0.06555(18) 0.02540(16) 0.0345(3) Uani 1 1 d . . . . .
H005 H -0.2829 -0.1315 -0.0330 0.041 Uiso 1 1 calc R . . . .
C006 C -0.4412(2) 0.23082(19) -0.24410(16) 0.0349(3) Uani 1 1 d . . . . .
C007 C -0.0588(2) -0.01089(17) 0.23425(17) 0.0363(3) Uani 1 1 d . . . . .
H007 H -0.0636 0.0776 0.2272 0.044 Uiso 1 1 calc R . . . .
C008 C -0.3300(2) 0.09358(18) -0.10956(15) 0.0329(3) Uani 1 1 d . . . . .
C009 C 0.0331(2) -0.18205(19) 0.35186(16) 0.0372(4) Uani 1 1 d . . . . .
C010 C -0.2629(3) 0.33093(19) -0.04435(19) 0.0431(4) Uani 1 1 d . . . . .
H01A H -0.2530 0.4064 -0.0864 0.052 Uiso 1 1 calc R . . . .
H01B H -0.1453 0.3122 -0.0078 0.052 Uiso 1 1 calc R . . . .
C011 C -0.6110(2) 0.1012(2) -0.42036(17) 0.0437(4) Uani 1 1 d . . . . .
H011 H -0.6574 0.0207 -0.4612 0.052 Uiso 1 1 calc R . . . .
C012 C -0.2356(2) 0.05759(19) -0.00016(16) 0.0362(3) Uani 1 1 d . . . . .
H012 H -0.1766 0.1236 0.0568 0.043 Uiso 1 1 calc R . . . .
C013 C -0.4734(3) 0.3462(2) -0.2937(2) 0.0449(4) Uani 1 1 d . . . . .
H013 H -0.4291 0.4268 -0.2522 0.054 Uiso 1 1 calc R . . . .
C014 C -0.1367(2) -0.10334(17) 0.13704(15) 0.0314(3) Uani 1 1 d . . . . .
C015 C -0.1262(3) -0.23536(18) 0.15145(17) 0.0380(4) Uani 1 1 d . . . . .
H015 H -0.1773 -0.2980 0.0882 0.046 Uiso 1 1 calc R . . . .
C016 C -0.5743(3) 0.3355(3) -0.4076(2) 0.0525(5) Uani 1 1 d . . . . .
H016 H -0.5974 0.4107 -0.4433 0.063 Uiso 1 1 calc R . . . .
O017 O 0.1175(2) -0.20765(17) 0.46029(14) 0.0554(4) Uani 1 1 d . . . . .
C018 C -0.6423(3) 0.2146(3) -0.4704(2) 0.0501(5) Uani 1 1 d . . . . .
H018 H -0.7093 0.2109 -0.5469 0.060 Uiso 1 1 calc R . . . .
C019 C 0.0242(3) -0.04977(19) 0.33942(17) 0.0394(4) Uani 1 1 d . . . . .
H019 H 0.0750 0.0126 0.4030 0.047 Uiso 1 1 calc R . . . .
C020 C -0.3742(4) 0.3621(3) 0.0538(3) 0.0619(6) Uani 1 1 d . . . . .
H02A H -0.4910 0.3799 0.0177 0.093 Uiso 1 1 calc GR . . . .
H02B H -0.3221 0.4372 0.1078 0.093 Uiso 1 1 calc GR . . . .
H02C H -0.3799 0.2889 0.0977 0.093 Uiso 1 1 calc GR . . . .
C1 C -0.0420(3) -0.27570(18) 0.25716(18) 0.0404(4) Uani 1 1 d . . . . .
H1 H -0.0358 -0.3641 0.2646 0.048 Uiso 1 1 calc R . . . .
C2 C -0.5082(2) 0.11089(19) -0.30701(16) 0.0343(3) Uani 1 1 d . . . . .
C C 0.1149(4) -0.3399(3) 0.4854(2) 0.0645(7) Uani 1 1 d . . . . .
HA H 0.1747 -0.3919 0.4301 0.097 Uiso 1 1 calc GR . . . .
HB H -0.0050 -0.3734 0.4766 0.097 Uiso 1 1 calc GR . . . .
HC H 0.1731 -0.3431 0.5664 0.097 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
S002 C008 1.7173(18) . ?
S002 C2 1.7387(19) . ?
N1 C006 1.398(2) . ?
N1 C008 1.337(2) . ?
N1 C010 1.486(2) . ?
C005 H005 0.9300 . ?
C005 C012 1.342(3) . ?
C005 C014 1.447(2) . ?
C006 C013 1.393(3) . ?
C006 C2 1.390(3) . ?
C007 H007 0.9300 . ?
C007 C014 1.405(2) . ?
C007 C019 1.372(3) . ?
C008 C012 1.430(2) . ?
C009 O017 1.355(2) . ?
C009 C019 1.395(3) . ?
C009 C1 1.389(3) . ?
C010 H01A 0.9700 . ?
C010 H01B 0.9700 . ?
C010 C020 1.521(3) . ?
C011 H011 0.9300 . ?
C011 C018 1.377(3) . ?
C011 C2 1.387(3) . ?
C012 H012 0.9300 . ?
C013 H013 0.9300 . ?
C013 C016 1.384(3) . ?
C014 C015 1.398(2) . ?
C015 H015 0.9300 . ?
C015 C1 1.386(3) . ?
C016 H016 0.9300 . ?
C016 C018 1.400(4) . ?
O017 C 1.431(3) . ?
C018 H018 0.9300 . ?
C019 H019 0.9300 . ?
C020 H02A 0.9600 . ?
C020 H02B 0.9600 . ?
C020 H02C 0.9600 . ?
C1 H1 0.9300 . ?
C HA 0.9600 . ?
C HB 0.9600 . ?
C HC 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
C008 S002 C2 90.72(9) . . ?
C006 N1 C010 122.62(15) . . ?
C008 N1 C006 114.02(16) . . ?
C008 N1 C010 123.29(15) . . ?
C012 C005 H005 117.6 . . ?
C012 C005 C014 124.83(17) . . ?
C014 C005 H005 117.6 . . ?
C013 C006 N1 127.27(18) . . ?
C2 C006 N1 111.76(16) . . ?
C2 C006 C013 120.96(17) . . ?
C014 C007 H007 119.6 . . ?
C019 C007 H007 119.6 . . ?
C019 C007 C014 120.73(16) . . ?
N1 C008 S002 112.58(13) . . ?
N1 C008 C012 123.29(17) . . ?
C012 C008 S002 124.13(14) . . ?
O017 C009 C019 114.84(18) . . ?
O017 C009 C1 125.13(18) . . ?
C1 C009 C019 120.02(16) . . ?
N1 C010 H01A 109.4 . . ?
N1 C010 H01B 109.4 . . ?
N1 C010 C020 111.39(17) . . ?
H01A C010 H01B 108.0 . . ?
C020 C010 H01A 109.4 . . ?
C020 C010 H01B 109.4 . . ?
C018 C011 H011 121.1 . . ?
C018 C011 C2 117.7(2) . . ?
C2 C011 H011 121.1 . . ?
C005 C012 C008 124.07(18) . . ?
C005 C012 H012 118.0 . . ?
C008 C012 H012 118.0 . . ?
C006 C013 H013 121.5 . . ?
C016 C013 C006 117.0(2) . . ?
C016 C013 H013 121.5 . . ?
C007 C014 C005 122.10(16) . . ?
C015 C014 C005 120.15(16) . . ?
C015 C014 C007 117.75(16) . . ?
C014 C015 H015 119.0 . . ?
C1 C015 C014 121.97(18) . . ?
C1 C015 H015 119.0 . . ?
C013 C016 H016 119.1 . . ?
C013 C016 C018 121.9(2) . . ?
C018 C016 H016 119.1 . . ?
C009 O017 C 118.3(2) . . ?
C011 C018 C016 120.73(19) . . ?
C011 C018 H018 119.6 . . ?
C016 C018 H018 119.6 . . ?
C007 C019 C009 120.56(18) . . ?
C007 C019 H019 119.7 . . ?
C009 C019 H019 119.7 . . ?
C010 C020 H02A 109.5 . . ?
C010 C020 H02B 109.5 . . ?
C010 C020 H02C 109.5 . . ?
H02A C020 H02B 109.5 . . ?
H02A C020 H02C 109.5 . . ?
H02B C020 H02C 109.5 . . ?
C009 C1 H1 120.5 . . ?
C015 C1 C009 118.96(17) . . ?
C015 C1 H1 120.5 . . ?
C006 C2 S002 110.91(13) . . ?
C011 C2 S002 127.44(16) . . ?
C011 C2 C006 121.64(18) . . ?
O017 C HA 109.5 . . ?
O017 C HB 109.5 . . ?
O017 C HC 109.5 . . ?
HA C HB 109.5 . . ?
HA C HC 109.5 . . ?
HB C HC 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S002 C008 C012 C005 -1.4(3) . . . . ?
N1 C006 C013 C016 178.87(19) . . . . ?
N1 C006 C2 S002 -0.79(19) . . . . ?
N1 C006 C2 C011 -179.91(16) . . . . ?
N1 C008 C012 C005 178.14(17) . . . . ?
C005 C014 C015 C1 -179.63(17) . . . . ?
C006 N1 C008 S002 0.15(19) . . . . ?
C006 N1 C008 C012 -179.48(16) . . . . ?
C006 N1 C010 C020 99.7(2) . . . . ?
C006 C013 C016 C018 0.4(3) . . . . ?
C007 C014 C015 C1 -0.2(3) . . . . ?
C008 S002 C2 C006 0.74(13) . . . . ?
C008 S002 C2 C011 179.79(17) . . . . ?
C008 N1 C006 C013 -178.57(18) . . . . ?
C008 N1 C006 C2 0.4(2) . . . . ?
C008 N1 C010 C020 -77.1(2) . . . . ?
C010 N1 C006 C013 4.4(3) . . . . ?
C010 N1 C006 C2 -176.63(16) . . . . ?
C010 N1 C008 S002 177.18(14) . . . . ?
C010 N1 C008 C012 -2.4(3) . . . . ?
C012 C005 C014 C007 4.6(3) . . . . ?
C012 C005 C014 C015 -175.94(18) . . . . ?
C013 C006 C2 S002 178.28(15) . . . . ?
C013 C006 C2 C011 -0.8(3) . . . . ?
C013 C016 C018 C011 0.1(3) . . . . ?
C014 C005 C012 C008 -177.95(17) . . . . ?
C014 C007 C019 C009 0.1(3) . . . . ?
C014 C015 C1 C009 0.5(3) . . . . ?
O017 C009 C019 C007 -179.57(18) . . . . ?
O017 C009 C1 C015 179.27(19) . . . . ?
C018 C011 C2 S002 -177.62(15) . . . . ?
C018 C011 C2 C006 1.3(3) . . . . ?
C019 C007 C014 C005 179.33(17) . . . . ?
C019 C007 C014 C015 -0.1(3) . . . . ?
C019 C009 O017 C 172.9(2) . . . . ?
C019 C009 C1 C015 -0.5(3) . . . . ?
C1 C009 O017 C -6.8(3) . . . . ?
C1 C009 C019 C007 0.2(3) . . . . ?
C2 S002 C008 N1 -0.51(13) . . . . ?
C2 S002 C008 C012 179.12(16) . . . . ?
C2 C006 C013 C016 -0.1(3) . . . . ?
C2 C011 C018 C016 -1.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

