# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_p-1
_database_code_depnum_ccdc_archive 'CCDC 1056057'
_audit_update_record             
;
2015-03-25 deposited with the CCDC.
2015-05-18 downloaded from the CCDC.
;
_audit_creation_date             2015-03-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_formula_moiety         'I, C20 H22 N O3 S, O'
_chemical_formula_sum            'C20 H22 I N O4 S'
_chemical_formula_weight         499.37
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.7237(5)
_cell_length_b                   10.2576(6)
_cell_length_c                   13.6801(8)
_cell_angle_alpha                78.320(2)
_cell_angle_beta                 84.144(2)
_cell_angle_gamma                76.520(2)
_cell_volume                     1030.43(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9901
_cell_measurement_temperature    123.15
_cell_measurement_theta_max      30.591
_cell_measurement_theta_min      2.338
_exptl_absorpt_coefficient_mu    1.680
_exptl_absorpt_correction_T_max  0.9916
_exptl_absorpt_correction_T_min  0.7192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadbs
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.6093
_exptl_crystal_density_meas      .
_exptl_crystal_description       plate
_exptl_crystal_F_000             499.6365
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.005
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_unetI/netI     0.0740
_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       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15967
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         30.60
_diffrn_reflns_theta_min         2.34
_diffrn_ambient_temperature      123.15
_diffrn_measured_fraction_theta_full 0.9877
_diffrn_measured_fraction_theta_max 0.9864
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -10
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                5329
_reflns_number_total             6250
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         2.8840
_refine_diff_density_min         -1.0084
_refine_diff_density_rms         0.2827
_refine_ls_d_res_high            0.6982
_refine_ls_d_res_low             8.7111
_refine_ls_goodness_of_fit_ref   0.9894
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    35
_refine_ls_number_parameters     244
_refine_ls_number_reflns         6250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0637
_refine_ls_restrained_S_all      0.9894
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1144P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1517
_refine_ls_wR_factor_ref         0.1615
_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:
 C19(H19a,H19b)
2.b Me refined with riding coordinates:
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c), C20(H20a,H20b,H20c)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C8(H8), C9(H9), C14(H14), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
I1 I 0.14009(3) 0.13110(2) 0.309073(16) 0.02404(11) Uani 1.000000 .
S1 S 0.12191(11) 0.53045(8) 0.63369(6) 0.01911(18) Uani 1.000000 .
O1 O 0.6475(4) 0.3422(3) 0.1317(2) 0.0245(5) Uani 1.000000 .
O2 O 0.6785(4) 0.5830(3) 0.0481(2) 0.0266(6) Uani 1.000000 .
O3 O -0.1887(4) 0.1622(3) 0.9476(2) 0.0274(6) Uani 1.000000 .
N1 N 0.1346(4) 0.2822(3) 0.6265(2) 0.0178(5) Uani 1.000000 .
C1 C 0.1851(5) 0.3933(4) 0.5742(3) 0.0181(6) Uani 1.000000 .
C2 C 0.2815(5) 0.3988(4) 0.4786(3) 0.0205(6) Uani 1.000000 .
H2 H 0.3133(5) 0.3187(4) 0.4501(3) 0.0245(8) Uiso 1.000000 R
C3 C 0.3285(5) 0.5136(4) 0.4276(3) 0.0204(6) Uani 1.000000 .
H3 H 0.2962(5) 0.5917(4) 0.4584(3) 0.0244(8) Uiso 1.000000 R
C4 C 0.4234(5) 0.5293(4) 0.3305(3) 0.0202(6) Uani 1.000000 .
C5 C 0.4906(5) 0.4195(3) 0.2800(3) 0.0199(6) Uani 1.000000 .
H5 H 0.4765(5) 0.3305(3) 0.3104(3) 0.0239(7) Uiso 1.000000 R
C6 C 0.5769(5) 0.4410(4) 0.1866(3) 0.0202(6) Uani 1.000000 .
C7 C 0.5974(5) 0.5730(4) 0.1406(3) 0.0210(6) Uani 1.000000 .
C8 C 0.5363(5) 0.6806(4) 0.1913(3) 0.0213(6) Uani 1.000000 .
H8 H 0.5534(5) 0.7691(4) 0.1616(3) 0.0256(8) Uiso 1.000000 R
C9 C 0.4500(5) 0.6592(4) 0.2856(3) 0.0208(6) Uani 1.000000 .
H9 H 0.4087(5) 0.7333(4) 0.3200(3) 0.0249(8) Uiso 1.000000 R
C10 C 0.6533(6) 0.2037(4) 0.1809(3) 0.0259(7) Uani 1.000000 .
H10a H 0.7064(6) 0.1421(4) 0.1344(3) 0.0388(11) Uiso 1.000000 R
H10b H 0.7256(6) 0.1823(4) 0.2392(3) 0.0388(11) Uiso 1.000000 R
H10c H 0.5320(6) 0.1922(4) 0.2025(3) 0.0388(11) Uiso 1.000000 R
C11 C 0.6931(6) 0.7160(4) -0.0023(3) 0.0313(8) Uani 1.000000 .
H11a H 0.7538(6) 0.7108(4) -0.0683(3) 0.0470(13) Uiso 1.000000 R
H11b H 0.5736(6) 0.7748(4) -0.0101(3) 0.0470(13) Uiso 1.000000 R
H11c H 0.7617(6) 0.7541(4) 0.0369(3) 0.0470(13) Uiso 1.000000 R
C12 C 0.0279(5) 0.4328(3) 0.7335(3) 0.0187(6) Uani 1.000000 .
C13 C 0.0445(4) 0.3007(4) 0.7184(3) 0.0190(6) Uani 1.000000 .
C14 C -0.0240(5) 0.2028(4) 0.7878(3) 0.0198(6) Uani 1.000000 .
H14 H -0.0121(5) 0.1126(4) 0.7767(3) 0.0238(7) Uiso 1.000000 R
C15 C -0.1108(5) 0.2444(4) 0.8741(3) 0.0207(6) Uani 1.000000 .
C16 C -0.1259(5) 0.3769(4) 0.8910(3) 0.0229(7) Uani 1.000000 .
H16 H -0.1843(5) 0.4015(4) 0.9513(3) 0.0275(8) Uiso 1.000000 R
C17 C -0.0578(5) 0.4717(4) 0.8221(3) 0.0219(7) Uani 1.000000 .
H17 H -0.0683(5) 0.5614(4) 0.8339(3) 0.0262(8) Uiso 1.000000 R
C18 C -0.1948(6) 0.0311(4) 0.9299(3) 0.0312(8) Uani 1.000000 .
H18a H -0.254(4) 0.0416(4) 0.8680(14) 0.0467(12) Uiso 1.000000 GR
H18b H -0.0731(6) -0.0233(13) 0.924(3) 0.0467(12) Uiso 1.000000 GR
H18c H -0.261(4) -0.0151(15) 0.9860(13) 0.0467(12) Uiso 1.000000 GR
C19 C 0.1794(5) 0.1486(4) 0.5938(3) 0.0217(7) Uani 1.000000 .
H19a H 0.0943(5) 0.0926(4) 0.6273(3) 0.0260(8) Uiso 1.000000 R
H19b H 0.1684(5) 0.1628(4) 0.5208(3) 0.0260(8) Uiso 1.000000 R
C20 C 0.3667(5) 0.0743(4) 0.6188(3) 0.0282(8) Uani 1.000000 .
H20a H 0.3937(5) -0.0137(4) 0.5966(3) 0.0422(12) Uiso 1.000000 R
H20b H 0.4510(5) 0.1291(4) 0.5848(3) 0.0422(12) Uiso 1.000000 R
H20c H 0.3770(5) 0.0590(4) 0.6913(3) 0.0422(12) Uiso 1.000000 R
O1W O 0.7679(4) 0.1758(3) 0.4970(3) 0.0367(7) Uani 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.715(3) . ?
S1 C12 1.726(3) . ?
O1 C6 1.362(4) . ?
O1 C10 1.436(4) . ?
O2 C7 1.350(4) . ?
O2 C11 1.423(5) . ?
O3 C15 1.361(4) . ?
O3 C18 1.426(5) . ?
N1 C1 1.335(5) . ?
N1 C13 1.398(4) . ?
N1 C19 1.482(4) . ?
C1 C2 1.436(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.349(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.449(5) . ?
C4 C5 1.408(5) . ?
C4 C9 1.401(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.381(5) . ?
C6 C7 1.410(5) . ?
C7 C8 1.386(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.392(5) . ?
C9 H9 0.9500 . ?
C10 H10a 0.9800 . ?
C10 H10b 0.9800 . ?
C10 H10c 0.9800 . ?
C11 H11a 0.9800 . ?
C11 H11b 0.9800 . ?
C11 H11c 0.9800 . ?
C12 C13 1.386(5) . ?
C12 C17 1.405(5) . ?
C13 C14 1.396(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.391(5) . ?
C15 C16 1.400(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.370(5) . ?
C17 H17 0.9500 . ?
C18 H18a 0.9800 . ?
C18 H18b 0.9800 . ?
C18 H18c 0.9800 . ?
C19 H19a 0.9900 . ?
C19 H19b 0.9900 . ?
C19 C20 1.507(5) . ?
C20 H20a 0.9800 . ?
C20 H20b 0.9800 . ?
C20 H20c 0.9800 . ?

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
C12 S1 C1 90.53(17) . . ?
C10 O1 C6 116.7(3) . . ?
C11 O2 C7 116.7(3) . . ?
C18 O3 C15 117.5(3) . . ?
C13 N1 C1 114.0(3) . . ?
C19 N1 C1 123.3(3) . . ?
C19 N1 C13 122.6(3) . . ?
N1 C1 S1 112.6(2) . . ?
C2 C1 S1 123.2(3) . . ?
C2 C1 N1 124.2(3) . . ?
H2 C2 C1 118.8(2) . . ?
C3 C2 C1 122.3(3) . . ?
C3 C2 H2 118.8(2) . . ?
H3 C3 C2 116.9(2) . . ?
C4 C3 C2 126.2(3) . . ?
C4 C3 H3 116.9(2) . . ?
C5 C4 C3 122.7(3) . . ?
C9 C4 C3 118.3(3) . . ?
C9 C4 C5 119.0(3) . . ?
H5 C5 C4 119.9(2) . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9(2) . . ?
C5 C6 O1 125.0(3) . . ?
C7 C6 O1 114.7(3) . . ?
C7 C6 C5 120.3(3) . . ?
C6 C7 O2 115.4(3) . . ?
C8 C7 O2 125.0(3) . . ?
C8 C7 C6 119.6(3) . . ?
H8 C8 C7 120.0(2) . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H8 120.0(2) . . ?
C8 C9 C4 120.7(3) . . ?
H9 C9 C4 119.7(2) . . ?
H9 C9 C8 119.7(2) . . ?
H10a C10 O1 109.5 . . ?
H10b C10 O1 109.5 . . ?
H10b C10 H10a 109.5 . . ?
H10c C10 O1 109.5 . . ?
H10c C10 H10a 109.5 . . ?
H10c C10 H10b 109.5 . . ?
H11a C11 O2 109.5 . . ?
H11b C11 O2 109.5 . . ?
H11b C11 H11a 109.5 . . ?
H11c C11 O2 109.5 . . ?
H11c C11 H11a 109.5 . . ?
H11c C11 H11b 109.5 . . ?
C13 C12 S1 111.6(3) . . ?
C17 C12 S1 128.3(3) . . ?
C17 C12 C13 120.1(3) . . ?
C12 C13 N1 111.3(3) . . ?
C14 C13 N1 126.3(3) . . ?
C14 C13 C12 122.4(3) . . ?
H14 C14 C13 121.8(2) . . ?
C15 C14 C13 116.4(3) . . ?
C15 C14 H14 121.8(2) . . ?
C14 C15 O3 123.5(3) . . ?
C16 C15 O3 114.9(3) . . ?
C16 C15 C14 121.6(3) . . ?
H16 C16 C15 119.4(2) . . ?
C17 C16 C15 121.2(3) . . ?
C17 C16 H16 119.4(2) . . ?
C16 C17 C12 118.3(3) . . ?
H17 C17 C12 120.9(2) . . ?
H17 C17 C16 120.9(2) . . ?
H18a C18 O3 109.5 . . ?
H18b C18 O3 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 O3 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 109.5 . . ?
H19a C19 N1 109.50(18) . . ?
H19b C19 N1 109.50(18) . . ?
H19b C19 H19a 108.1 . . ?
C20 C19 N1 110.7(3) . . ?
C20 C19 H19a 109.5(2) . . ?
C20 C19 H19b 109.5(2) . . ?
H20a C20 C19 109.5 . . ?
H20b C20 C19 109.5 . . ?
H20b C20 H20a 109.5 . . ?
H20c C20 C19 109.5 . . ?
H20c C20 H20a 109.5 . . ?
H20c C20 H20b 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p-1
_database_code_depnum_ccdc_archive 'CCDC 1056058'
_audit_update_record             
;
2015-03-25 deposited with the CCDC.
2015-05-18 downloaded from the CCDC.
;
_audit_creation_date             2015-03-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_formula_moiety         'I, C20 H22 N O3 S, 0.5(O)'
_chemical_formula_sum            'C20 H22 I N O3.5 S'
_chemical_formula_weight         491.37
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.4692(4)
_cell_length_b                   15.9898(9)
_cell_length_c                   18.4114(11)
_cell_angle_alpha                110.533(2)
_cell_angle_beta                 91.966(2)
_cell_angle_gamma                94.712(2)
_cell_volume                     2047.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9899
_cell_measurement_theta_max      30.585
_cell_measurement_theta_min      2.368
_exptl_absorpt_coefficient_mu    1.688
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6223
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.5939
_exptl_crystal_density_meas      .
_exptl_crystal_description       prism
_exptl_crystal_F_000             983.2515
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            31145
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.28
_diffrn_ambient_temperature      123.15
_diffrn_measured_fraction_theta_full 0.9828
_diffrn_measured_fraction_theta_max 0.9845
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              20
_reflns_limit_k_min              -21
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                9654
_reflns_number_total             10716
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         4.1516
_refine_diff_density_min         -0.8272
_refine_diff_density_rms         0.3028
_refine_ls_d_res_high            0.7330
_refine_ls_d_res_low             8.9506
_refine_ls_goodness_of_fit_ref   1.0103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    70
_refine_ls_number_parameters     485
_refine_ls_number_reflns         10716
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0582
_refine_ls_restrained_S_all      1.0103
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1090P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1366
_refine_ls_wR_factor_ref         0.1421
_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:
 C19(H19a,H19b), C19A(H19c,H19d)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C8(H8), C9(H9), C14(H14), C16(H16), C17(H17),
 C2A(H2A), C3A(H3A), C5A(H5A), C8A(H8A), C9A(H9A), C14A(H14A), C16A(H16A),
 C17A(H17A)
2.c Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c), C18(H18a,H18b,H18c), C20(H20a,H20b,
 H20c), C10A(H10d,H10e,H10f), C11A(H11d,H11e,H11f), C18A(H18d,H18e,H18f),
 C20A(H20d,H20e,H20f)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
I1 I -0.10556(2) 0.735902(11) 0.386537(9) 0.02269(8) Uani 1.000000 .
I2 I 0.58320(2) 0.779174(11) 0.105386(9) 0.02296(8) Uani 1.000000 .
S1 S 0.15792(8) 1.14266(4) 0.39494(3) 0.02115(13) Uani 1.000000 .
O1 O 0.3666(3) 0.77860(12) 0.58069(11) 0.0304(4) Uani 1.000000 .
O2 O 0.4716(3) 0.88826(13) 0.71803(10) 0.0250(4) Uani 1.000000 .
O3 O -0.1700(3) 1.08034(14) 0.08620(12) 0.0335(5) Uani 1.000000 .
N1 N 0.0322(3) 0.98864(14) 0.30117(12) 0.0181(4) Uani 1.000000 .
C1 C 0.1156(3) 1.02925(17) 0.37176(15) 0.0179(5) Uani 1.000000 .
C2 C 0.1675(3) 0.98369(17) 0.42288(14) 0.0195(5) Uani 1.000000 .
H2 H 0.1441(3) 0.92026(17) 0.40634(14) 0.0234(6) Uiso 1.000000 R
C3 C 0.2489(3) 1.02975(17) 0.49402(14) 0.0184(4) Uani 1.000000 .
H3 H 0.2690(3) 1.09307(17) 0.50823(14) 0.0221(5) Uiso 1.000000 R
C4 C 0.3092(3) 0.99233(18) 0.55130(15) 0.0192(5) Uani 1.000000 .
C5 C 0.3057(3) 0.89883(17) 0.53448(14) 0.0207(5) Uani 1.000000 .
H5 H 0.2644(3) 0.85799(17) 0.48417(14) 0.0248(6) Uiso 1.000000 R
C6 C 0.3626(3) 0.86663(17) 0.59150(15) 0.0226(5) Uani 1.000000 .
C7 C 0.4229(3) 0.92706(17) 0.66662(14) 0.0196(5) Uani 1.000000 .
C8 C 0.4291(3) 1.01855(18) 0.68263(15) 0.0215(5) Uani 1.000000 .
H8 H 0.4715(3) 1.05936(18) 0.73280(15) 0.0257(6) Uiso 1.000000 R
C9 C 0.3731(3) 1.05121(17) 0.62516(14) 0.0204(5) Uani 1.000000 .
H9 H 0.3787(3) 1.11414(17) 0.63658(14) 0.0245(5) Uiso 1.000000 R
C10 C 0.3348(5) 0.7163(2) 0.50313(17) 0.0437(8) Uani 1.000000 .
H10a H 0.423(2) 0.7311(11) 0.4702(4) 0.0656(12) Uiso 1.000000 GR
H10b H 0.346(3) 0.6554(3) 0.5026(3) 0.0656(12) Uiso 1.000000 GR
H10c H 0.2131(14) 0.7194(13) 0.4832(6) 0.0656(12) Uiso 1.000000 GR
C11 C 0.5429(4) 0.9468(2) 0.79303(15) 0.0259(5) Uani 1.000000 .
H11a H 0.6571(15) 0.9787(11) 0.7883(2) 0.0389(8) Uiso 1.000000 GR
H11b H 0.4572(14) 0.9903(9) 0.8163(6) 0.0389(8) Uiso 1.000000 GR
H11c H 0.563(3) 0.9116(3) 0.8262(4) 0.0389(8) Uiso 1.000000 GR
C12 C 0.0643(3) 1.13480(17) 0.30526(14) 0.0208(5) Uani 1.000000 .
C13 C 0.0018(3) 1.04664(18) 0.26128(15) 0.0192(5) Uani 1.000000 .
C14 C -0.0778(3) 1.02255(17) 0.18581(14) 0.0209(5) Uani 1.000000 .
H14 H -0.1190(3) 0.96204(17) 0.15555(14) 0.0251(6) Uiso 1.000000 R
C15 C -0.0934(4) 1.09167(18) 0.15754(15) 0.0249(5) Uani 1.000000 .
C16 C -0.0310(4) 1.18137(19) 0.20202(16) 0.0311(6) Uani 1.000000 .
H16 H -0.0435(4) 1.22705(19) 0.18085(16) 0.0373(7) Uiso 1.000000 R
C17 C 0.0477(4) 1.20339(17) 0.27572(15) 0.0273(5) Uani 1.000000 .
H17 H 0.0899(4) 1.26381(17) 0.30586(15) 0.0328(6) Uiso 1.000000 R
C18 C -0.2327(4) 0.99044(19) 0.03545(15) 0.0306(6) Uani 1.000000 .
H18a H -0.279(3) 0.9916(3) -0.0147(5) 0.0458(9) Uiso 1.000000 GR
H18b H -0.1330(9) 0.9527(4) 0.0274(11) 0.0458(9) Uiso 1.000000 GR
H18c H -0.329(2) 0.9658(6) 0.0591(6) 0.0458(9) Uiso 1.000000 GR
C19 C -0.0217(3) 0.89087(16) 0.26556(14) 0.0200(4) Uani 1.000000 .
H19a H -0.0426(3) 0.86605(16) 0.30717(14) 0.0240(5) Uiso 1.000000 R
H19b H -0.1361(3) 0.88061(16) 0.23352(14) 0.0240(5) Uiso 1.000000 R
C20 C 0.1199(4) 0.84226(19) 0.21544(17) 0.0300(6) Uani 1.000000 .
H20a H 0.146(2) 0.8689(10) 0.1759(9) 0.0450(9) Uiso 1.000000 GR
H20b H 0.2301(11) 0.8476(13) 0.2479(3) 0.0450(9) Uiso 1.000000 GR
H20c H 0.0759(13) 0.7787(4) 0.1899(11) 0.0450(9) Uiso 1.000000 GR
S1A S 0.36122(9) 0.36715(4) 0.11681(4) 0.02186(13) Uani 1.000000 .
O1A O 0.0936(3) 0.71002(12) -0.08238(10) 0.0254(4) Uani 1.000000 .
O2A O 0.0215(3) 0.59749(13) -0.22223(11) 0.0266(4) Uani 1.000000 .
O3A O 0.6769(3) 0.46182(15) 0.43344(12) 0.0363(5) Uani 1.000000 .
N1A N 0.4570(3) 0.52765(14) 0.20667(12) 0.0184(4) Uani 1.000000 .
C1A C 0.3823(3) 0.48064(18) 0.13563(15) 0.0198(5) Uani 1.000000 .
C2A C 0.3243(3) 0.51987(18) 0.08078(15) 0.0204(5) Uani 1.000000 .
H2A H 0.3314(3) 0.58338(18) 0.09623(15) 0.0245(6) Uiso 1.000000 R
C3A C 0.2595(3) 0.46859(17) 0.00733(14) 0.0194(5) Uani 1.000000 .
H3A H 0.2559(3) 0.40534(17) -0.00662(14) 0.0233(5) Uiso 1.000000 R
C4A C 0.1952(3) 0.50185(17) -0.05167(15) 0.0188(5) Uani 1.000000 .
C5A C 0.1773(3) 0.59366(17) -0.03522(14) 0.0197(5) Uani 1.000000 .
H5A H 0.2070(3) 0.63560(17) 0.01587(14) 0.0236(5) Uiso 1.000000 R
C6A C 0.1168(3) 0.62284(16) -0.09306(14) 0.0194(5) Uani 1.000000 .
C7A C 0.0754(3) 0.56172(18) -0.16905(15) 0.0203(5) Uani 1.000000 .
C8A C 0.0891(3) 0.47070(17) -0.18517(14) 0.0204(5) Uani 1.000000 .
H8A H 0.0587(3) 0.42867(17) -0.23617(14) 0.0245(6) Uiso 1.000000 R
C9A C 0.1476(3) 0.44148(17) -0.12616(14) 0.0205(5) Uani 1.000000 .
H9A H 0.1548(3) 0.37923(17) -0.13721(14) 0.0246(6) Uiso 1.000000 R
C10A C 0.0853(4) 0.76914(17) -0.00349(15) 0.0265(5) Uani 1.000000 .
H10d H 0.059(3) 0.8284(4) -0.00284(16) 0.0398(8) Uiso 1.000000 GR
H10e H -0.010(2) 0.7447(7) 0.0210(4) 0.0398(8) Uiso 1.000000 GR
H10f H 0.2012(10) 0.7747(11) 0.0252(4) 0.0398(8) Uiso 1.000000 GR
C11A C -0.0369(4) 0.5367(2) -0.29804(15) 0.0282(6) Uani 1.000000 .
H11d H -0.071(3) 0.5705(2) -0.3308(4) 0.0422(8) Uiso 1.000000 GR
H11e H 0.0610(11) 0.5008(11) -0.3207(5) 0.0422(8) Uiso 1.000000 GR
H11f H -0.1410(19) 0.4969(10) -0.2949(2) 0.0422(8) Uiso 1.000000 GR
C12A C 0.4500(3) 0.38471(17) 0.20958(14) 0.0218(5) Uani 1.000000 .
C13A C 0.4951(3) 0.47560(18) 0.25108(15) 0.0201(5) Uani 1.000000 .
C14A C 0.5712(3) 0.50693(18) 0.32791(14) 0.0228(5) Uani 1.000000 .
H14A H 0.6018(3) 0.56911(18) 0.35607(14) 0.0274(6) Uiso 1.000000 R
C15A C 0.5997(4) 0.4426(2) 0.36063(15) 0.0274(6) Uani 1.000000 .
C16A C 0.5530(4) 0.35034(19) 0.31872(16) 0.0306(6) Uani 1.000000 .
H16A H 0.5732(4) 0.30790(19) 0.34278(16) 0.0368(7) Uiso 1.000000 R
C17A C 0.4791(4) 0.32108(19) 0.24387(16) 0.0282(5) Uani 1.000000 .
H17A H 0.4482(4) 0.25889(19) 0.21582(16) 0.0339(7) Uiso 1.000000 R
C18A C 0.7277(5) 0.5535(2) 0.47962(17) 0.0371(7) Uani 1.000000 .
H18d H 0.810(3) 0.5805(5) 0.4516(6) 0.0556(10) Uiso 1.000000 GR
H18e H 0.6200(6) 0.5858(4) 0.4902(12) 0.0556(10) Uiso 1.000000 GR
H18f H 0.788(3) 0.5572(2) 0.5288(6) 0.0556(10) Uiso 1.000000 GR
C19A C 0.4996(3) 0.62634(16) 0.23658(14) 0.0208(5) Uani 1.000000 .
H19c H 0.6117(3) 0.64239(16) 0.27084(14) 0.0250(6) Uiso 1.000000 R
H19d H 0.5208(3) 0.64678(16) 0.19241(14) 0.0250(6) Uiso 1.000000 R
C20A C 0.3493(4) 0.6743(2) 0.28160(18) 0.0316(6) Uani 1.000000 .
H20d H 0.2404(10) 0.6623(13) 0.2468(4) 0.0473(9) Uiso 1.000000 GR
H20e H 0.325(2) 0.6526(12) 0.3242(9) 0.0473(9) Uiso 1.000000 GR
H20f H 0.3855(13) 0.7390(2) 0.3029(12) 0.0473(9) Uiso 1.000000 GR
O1W O 0.4945(3) 0.17497(16) 0.07220(12) 0.0441(5) Uani 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.710(3) . ?
S1 C12 1.730(2) . ?
O1 C6 1.354(3) . ?
O1 C10 1.424(3) . ?
O2 C7 1.356(3) . ?
O2 C11 1.424(3) . ?
O3 C15 1.360(3) . ?
O3 C18 1.441(3) . ?
N1 C1 1.336(3) . ?
N1 C13 1.397(3) . ?
N1 C19 1.482(3) . ?
C1 C2 1.438(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.350(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.458(3) . ?
C4 C5 1.414(4) . ?
C4 C9 1.395(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(3) . ?
C6 C7 1.414(4) . ?
C7 C8 1.384(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.400(3) . ?
C9 H9 0.9500 . ?
C10 H10a 0.9800 . ?
C10 H10b 0.9800 . ?
C10 H10c 0.9800 . ?
C11 H11a 0.9800 . ?
C11 H11b 0.9800 . ?
C11 H11c 0.9800 . ?
C12 C13 1.388(4) . ?
C12 C17 1.396(3) . ?
C13 C14 1.401(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(3) . ?
C15 C16 1.409(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.374(4) . ?
C17 H17 0.9500 . ?
C18 H18a 0.9800 . ?
C18 H18b 0.9800 . ?
C18 H18c 0.9800 . ?
C19 H19a 0.9900 . ?
C19 H19b 0.9900 . ?
C19 C20 1.508(4) . ?
C20 H20a 0.9800 . ?
C20 H20b 0.9800 . ?
C20 H20c 0.9800 . ?
S1A C1A 1.716(3) . ?
S1A C12A 1.730(3) . ?
O1A C6A 1.364(3) . ?
O1A C10A 1.435(3) . ?
O2A C7A 1.361(3) . ?
O2A C11A 1.421(3) . ?
O3A C15A 1.361(3) . ?
O3A C18A 1.423(4) . ?
N1A C1A 1.334(3) . ?
N1A C13A 1.394(3) . ?
N1A C19A 1.480(3) . ?
C1A C2A 1.435(3) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.359(4) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.451(3) . ?
C4A C5A 1.410(3) . ?
C4A C9A 1.386(3) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.381(3) . ?
C6A C7A 1.403(3) . ?
C7A C8A 1.393(4) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.395(3) . ?
C9A H9A 0.9500 . ?
C10A H10d 0.9800 . ?
C10A H10e 0.9800 . ?
C10A H10f 0.9800 . ?
C11A H11d 0.9800 . ?
C11A H11e 0.9800 . ?
C11A H11f 0.9800 . ?
C12A C13A 1.390(3) . ?
C12A C17A 1.399(3) . ?
C13A C14A 1.406(3) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.388(4) . ?
C15A C16A 1.412(4) . ?
C16A H16A 0.9500 . ?
C16A C17A 1.370(4) . ?
C17A H17A 0.9500 . ?
C18A H18d 0.9800 . ?
C18A H18e 0.9800 . ?
C18A H18f 0.9800 . ?
C19A H19c 0.9900 . ?
C19A H19d 0.9900 . ?
C19A C20A 1.515(4) . ?
C20A H20d 0.9800 . ?
C20A H20e 0.9800 . ?
C20A H20f 0.9800 . ?

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
C12 S1 C1 90.99(12) . . ?
C10 O1 C6 117.2(2) . . ?
C11 O2 C7 116.9(2) . . ?
C18 O3 C15 118.0(2) . . ?
C13 N1 C1 114.0(2) . . ?
C19 N1 C1 124.6(2) . . ?
C19 N1 C13 121.4(2) . . ?
N1 C1 S1 112.45(19) . . ?
C2 C1 S1 123.0(2) . . ?
C2 C1 N1 124.5(2) . . ?
H2 C2 C1 119.52(15) . . ?
C3 C2 C1 121.0(2) . . ?
C3 C2 H2 119.52(15) . . ?
H3 C3 C2 116.64(15) . . ?
C4 C3 C2 126.7(2) . . ?
C4 C3 H3 116.64(15) . . ?
C5 C4 C3 122.4(2) . . ?
C9 C4 C3 118.6(2) . . ?
C9 C4 C5 119.1(2) . . ?
H5 C5 C4 119.97(14) . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 H5 119.97(15) . . ?
C5 C6 O1 124.4(2) . . ?
C7 C6 O1 115.4(2) . . ?
C7 C6 C5 120.2(2) . . ?
C6 C7 O2 115.2(2) . . ?
C8 C7 O2 125.1(2) . . ?
C8 C7 C6 119.7(2) . . ?
H8 C8 C7 119.87(15) . . ?
C9 C8 C7 120.3(2) . . ?
C9 C8 H8 119.87(15) . . ?
C8 C9 C4 120.7(2) . . ?
H9 C9 C4 119.65(15) . . ?
H9 C9 C8 119.65(15) . . ?
H10a C10 O1 109.5 . . ?
H10b C10 O1 109.5 . . ?
H10b C10 H10a 109.5 . . ?
H10c C10 O1 109.5 . . ?
H10c C10 H10a 109.5 . . ?
H10c C10 H10b 109.5 . . ?
H11a C11 O2 109.5 . . ?
H11b C11 O2 109.5 . . ?
H11b C11 H11a 109.5 . . ?
H11c C11 O2 109.5 . . ?
H11c C11 H11a 109.5 . . ?
H11c C11 H11b 109.5 . . ?
C13 C12 S1 110.91(18) . . ?
C17 C12 S1 128.4(2) . . ?
C17 C12 C13 120.7(2) . . ?
C12 C13 N1 111.6(2) . . ?
C14 C13 N1 126.5(2) . . ?
C14 C13 C12 121.9(2) . . ?
H14 C14 C13 121.73(15) . . ?
C15 C14 C13 116.5(2) . . ?
C15 C14 H14 121.73(16) . . ?
C14 C15 O3 124.2(2) . . ?
C16 C15 O3 114.0(2) . . ?
C16 C15 C14 121.9(2) . . ?
H16 C16 C15 119.70(15) . . ?
C17 C16 C15 120.6(2) . . ?
C17 C16 H16 119.70(16) . . ?
C16 C17 C12 118.4(2) . . ?
H17 C17 C12 120.80(15) . . ?
H17 C17 C16 120.80(16) . . ?
H18a C18 O3 109.5 . . ?
H18b C18 O3 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 O3 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 109.5 . . ?
H19a C19 N1 109.25(12) . . ?
H19b C19 N1 109.25(12) . . ?
H19b C19 H19a 107.9 . . ?
C20 C19 N1 111.8(2) . . ?
C20 C19 H19a 109.25(15) . . ?
C20 C19 H19b 109.25(15) . . ?
H20a C20 C19 109.5 . . ?
H20b C20 C19 109.5 . . ?
H20b C20 H20a 109.5 . . ?
H20c C20 C19 109.5 . . ?
H20c C20 H20a 109.5 . . ?
H20c C20 H20b 109.5 . . ?
C12A S1A C1A 90.68(13) . . ?
C10A O1A C6A 116.33(19) . . ?
C11A O2A C7A 117.3(2) . . ?
C18A O3A C15A 118.1(2) . . ?
C13A N1A C1A 114.2(2) . . ?
C19A N1A C1A 123.8(2) . . ?
C19A N1A C13A 122.0(2) . . ?
N1A C1A S1A 112.46(19) . . ?
C2A C1A S1A 123.3(2) . . ?
C2A C1A N1A 124.2(2) . . ?
H2A C2A C1A 119.12(15) . . ?
C3A C2A C1A 121.8(2) . . ?
C3A C2A H2A 119.12(15) . . ?
H3A C3A C2A 117.09(15) . . ?
C4A C3A C2A 125.8(2) . . ?
C4A C3A H3A 117.09(14) . . ?
C5A C4A C3A 122.0(2) . . ?
C9A C4A C3A 119.1(2) . . ?
C9A C4A C5A 119.0(2) . . ?
H5A C5A C4A 119.87(14) . . ?
C6A C5A C4A 120.3(2) . . ?
C6A C5A H5A 119.87(15) . . ?
C5A C6A O1A 124.4(2) . . ?
C7A C6A O1A 115.3(2) . . ?
C7A C6A C5A 120.4(2) . . ?
C6A C7A O2A 115.9(2) . . ?
C8A C7A O2A 124.6(2) . . ?
C8A C7A C6A 119.5(2) . . ?
H8A C8A C7A 120.12(15) . . ?
C9A C8A C7A 119.8(2) . . ?
C9A C8A H8A 120.12(15) . . ?
C8A C9A C4A 121.0(2) . . ?
H9A C9A C4A 119.49(15) . . ?
H9A C9A C8A 119.49(15) . . ?
H10d C10A O1A 109.5 . . ?
H10e C10A O1A 109.5 . . ?
H10e C10A H10d 109.5 . . ?
H10f C10A O1A 109.5 . . ?
H10f C10A H10d 109.5 . . ?
H10f C10A H10e 109.5 . . ?
H11d C11A O2A 109.5 . . ?
H11e C11A O2A 109.5 . . ?
H11e C11A H11d 109.5 . . ?
H11f C11A O2A 109.5 . . ?
H11f C11A H11d 109.5 . . ?
H11f C11A H11e 109.5 . . ?
C13A C12A S1A 111.12(19) . . ?
C17A C12A S1A 128.5(2) . . ?
C17A C12A C13A 120.4(2) . . ?
C12A C13A N1A 111.5(2) . . ?
C14A C13A N1A 126.6(2) . . ?
C14A C13A C12A 121.9(2) . . ?
H14A C14A C13A 121.61(15) . . ?
C15A C14A C13A 116.8(2) . . ?
C15A C14A H14A 121.61(16) . . ?
C14A C15A O3A 123.9(3) . . ?
C16A C15A O3A 114.6(2) . . ?
C16A C15A C14A 121.4(2) . . ?
H16A C16A C15A 119.52(15) . . ?
C17A C16A C15A 121.0(2) . . ?
C17A C16A H16A 119.52(16) . . ?
C16A C17A C12A 118.6(3) . . ?
H17A C17A C12A 120.70(16) . . ?
H17A C17A C16A 120.70(16) . . ?
H18d C18A O3A 109.5 . . ?
H18e C18A O3A 109.5 . . ?
H18e C18A H18d 109.5 . . ?
H18f C18A O3A 109.5 . . ?
H18f C18A H18d 109.5 . . ?
H18f C18A H18e 109.5 . . ?
H19c C19A N1A 109.21(12) . . ?
H19d C19A N1A 109.21(12) . . ?
H19d C19A H19c 107.9 . . ?
C20A C19A N1A 112.0(2) . . ?
C20A C19A H19c 109.21(15) . . ?
C20A C19A H19d 109.21(15) . . ?
H20d C20A C19A 109.5 . . ?
H20e C20A C19A 109.5 . . ?
H20e C20A H20d 109.5 . . ?
H20f C20A C19A 109.5 . . ?
H20f C20A H20d 109.5 . . ?
H20f C20A H20e 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p-1
_database_code_depnum_ccdc_archive 'CCDC 1056059'
_audit_update_record             
;
2015-05-13 deposited with the CCDC.
2015-05-18 downloaded from the CCDC.
;
_audit_creation_date             2015-05-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_formula_moiety         'I, C20 H22 N O3 S, 0.4(O)'
_chemical_formula_sum            'C20 H22 I N O3.4 S'
_chemical_formula_weight         489.77
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.484(5)
_cell_length_b                   10.197(7)
_cell_length_c                   14.512(10)
_cell_angle_alpha                94.449(10)
_cell_angle_beta                 103.752(11)
_cell_angle_gamma                105.623(10)
_cell_volume                     1024.1(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4064
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      29.87
_cell_measurement_theta_min      2.37
_exptl_absorpt_coefficient_mu    1.687
_exptl_absorpt_correction_T_max  0.84352
_exptl_absorpt_correction_T_min  0.68431
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.5882
_exptl_crystal_density_meas      .
_exptl_crystal_description       plate
_exptl_crystal_F_000             490.0236
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.02
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0448
_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       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9357
_diffrn_reflns_theta_full        26.9996
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.37
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.9696
_diffrn_measured_fraction_theta_max 0.9696
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              12
_reflns_limit_k_min              -13
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                3637
_reflns_number_total             4331
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_refine_diff_density_max         0.8092
_refine_diff_density_min         -0.9617
_refine_diff_density_rms         0.1015
_refine_ls_d_res_high            0.7828
_refine_ls_d_res_low             8.5984
_refine_ls_goodness_of_fit_ref   1.0314
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    52
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4331
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0319
_refine_ls_restrained_S_all      1.0314
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0301P)²+1.1149P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0783
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: I1b(0.5) S1b(0.5) N1b(0.5) C10A(0.5) H10a(0.5) H10b(0.5) H10c(0.5)
 C10B(0.5) H10d(0.5) H10e(0.5) H10f(0.5) C12A(0.5) C13A(0.5) C14A(0.5)
 H14A(0.5) C15A(0.5) C16A(0.5) H16A(0.5) C17A(0.5) H17A(0.5) C18A(0.5)
 H18a(0.5) H18b(0.5) H18c(0.5) O3A(0.5) C12B(0.5) C13B(0.5) C14B(0.5) H14B(0.5)
 C15B(0.5) C16B(0.5) H16B(0.5) C17B(0.5) H17B(0.5) C18B(0.5) H18d(0.5)
 H18e(0.5) H18f(0.5) O3B(0.5) H19c(0.5) H19d(0.5) H19a(0.5) H19b(0.5) O1W(0.4)
 I1a(0.5) N1a(0.5) S1a(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C19(H19c,H19d), C19(H19a,H19b)
3.b Me refined with riding coordinates:
 C10A(H10a,H10b,H10c), C10B(H10d,H10e,H10f), C11(H11a,H11b,H11c), C18A(H18a,
 H18b,H18c), C20(H20a,H20b,H20c)
3.c Me refined as rotating group:
 C18B(H18d,H18e,H18f)
3.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C8(H8), C9(H9), C14A(H14A), C16A(H16A), C17A(H17A),
 C14B(H14B), C16B(H16B), C17B(H17B)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
_atom_site_disorder_group
I1b I 0.3023(4) -0.3850(4) -0.1720(2) 0.0317(4) Uani 0.500000 . 2
S1b S 0.5044(4) 0.0220(3) 0.2477(2) 0.0320(9) Uiso 0.500000 . 2
O1 O -0.1051(4) -0.1333(2) -0.29693(17) 0.0453(6) Uani 1.000000 . .
O2 O -0.0836(3) 0.1154(2) -0.32448(16) 0.0378(5) Uani 1.000000 . .
N1b N 0.4312(11) -0.2337(8) 0.1793(6) 0.023(2) Uiso 0.500000 . 2
C1 C 0.4096(4) -0.1069(3) 0.1547(2) 0.0254(6) Uani 1.000000 . .
C2 C 0.3115(4) -0.0960(3) 0.0606(2) 0.0266(6) Uani 1.000000 . .
H2 H 0.2622(4) -0.1758(3) 0.0131(2) 0.0319(7) Uiso 1.000000 R .
C3 C 0.2862(4) 0.0233(3) 0.0364(2) 0.0258(6) Uani 1.000000 . .
H3 H 0.3385(4) 0.1010(3) 0.0856(2) 0.0309(7) Uiso 1.000000 R .
C4 C 0.1876(4) 0.0463(3) -0.0567(2) 0.0234(6) Uani 1.000000 . .
C5 C 0.0880(4) -0.0614(3) -0.1325(2) 0.0268(6) Uani 1.000000 . .
H5 H 0.0832(4) -0.1534(3) -0.1234(2) 0.0321(7) Uiso 1.000000 R .
C6 C -0.0029(4) -0.0356(3) -0.2198(2) 0.0293(6) Uani 1.000000 . .
C7 C 0.0065(4) 0.1015(3) -0.2344(2) 0.0262(6) Uani 1.000000 . .
C8 C 0.1020(4) 0.2076(3) -0.1596(2) 0.0292(6) Uani 1.000000 . .
H8 H 0.1070(4) 0.2996(3) -0.1686(2) 0.0350(8) Uiso 1.000000 R .
C9 C 0.1912(4) 0.1802(3) -0.0710(2) 0.0289(6) Uani 1.000000 . .
H9 H 0.2554(4) 0.2539(3) -0.0194(2) 0.0346(8) Uiso 1.000000 R .
C10A C -0.1165(12) -0.2779(8) -0.2865(6) 0.0413(17) Uiso 0.500000 . 1
H10a H -0.1939(12) -0.3377(8) -0.3469(6) 0.062(3) Uiso 0.500000 R 1
H10b H 0.0136(12) -0.2878(8) -0.2708(6) 0.062(3) Uiso 0.500000 R 1
H10c H -0.1766(12) -0.3042(8) -0.2350(6) 0.062(3) Uiso 0.500000 R 1
C10B C -0.1848(10) -0.2684(6) -0.2730(5) 0.0284(13) Uiso 0.500000 . 2
H10d H -0.2563(10) -0.3330(6) -0.3320(5) 0.043(2) Uiso 0.500000 R 2
H10e H -0.0800(10) -0.3007(6) -0.2377(5) 0.043(2) Uiso 0.500000 R 2
H10f H -0.2719(10) -0.2626(6) -0.2330(5) 0.043(2) Uiso 0.500000 R 2
C11 C -0.0896(5) 0.2508(4) -0.3404(3) 0.0403(8) Uani 1.000000 . .
H11a H -0.1577(5) 0.2482(4) -0.4075(3) 0.0604(12) Uiso 1.000000 R .
H11b H -0.1573(5) 0.2845(4) -0.2981(3) 0.0604(12) Uiso 1.000000 R .
H11c H 0.0421(5) 0.3125(4) -0.3266(3) 0.0604(12) Uiso 1.000000 R .
C12A C 0.5707(10) -0.0617(8) 0.3278(5) 0.021(2) Uiso 0.500000 . 1
C13A C 0.5447(10) -0.1922(9) 0.2836(5) 0.0185(19) Uiso 0.500000 . 1
C14A C 0.6026(10) -0.2926(8) 0.3357(5) 0.0247(16) Uiso 0.500000 . 1
H14A H 0.5847(10) -0.3829(8) 0.3054(5) 0.030(2) Uiso 0.500000 R 1
C15A C 0.6864(10) -0.2516(10) 0.4327(5) 0.0281(16) Uiso 0.500000 . 1
C16A C 0.7126(11) -0.1196(10) 0.4770(6) 0.037(2) Uiso 0.500000 . 1
H16A H 0.7725(11) -0.0952(10) 0.5440(6) 0.045(2) Uiso 0.500000 R 1
C17A C 0.6537(12) -0.0237(10) 0.4262(6) 0.037(2) Uiso 0.500000 . 1
H17A H 0.6690(12) 0.0658(10) 0.4572(6) 0.044(3) Uiso 0.500000 R 1
C18A C 0.7237(11) -0.4742(10) 0.4538(6) 0.0395(17) Uiso 0.500000 . 1
H18a H 0.7786(11) -0.5216(10) 0.5044(6) 0.059(3) Uiso 0.500000 R 1
H18b H 0.5854(11) -0.5207(10) 0.4283(6) 0.059(3) Uiso 0.500000 R 1
H18c H 0.7871(11) -0.4761(10) 0.4021(6) 0.059(3) Uiso 0.500000 R 1
O3A O 0.7527(8) -0.3367(6) 0.4920(4) 0.0422(13) Uiso 0.500000 . 1
C12B C 0.5683(12) -0.0957(10) 0.3236(6) 0.030(2) Uiso 0.500000 . 2
C13B C 0.5230(11) -0.2267(9) 0.2756(6) 0.026(2) Uiso 0.500000 . 2
C14B C 0.5667(11) -0.3329(8) 0.3202(5) 0.0273(17) Uiso 0.500000 . 2
H14B H 0.5353(11) -0.4230(8) 0.2860(5) 0.033(2) Uiso 0.500000 R 2
C15B C 0.6586(10) -0.3014(9) 0.4173(5) 0.0300(17) Uiso 0.500000 . 2
C16B C 0.7039(11) -0.1694(11) 0.4670(7) 0.039(2) Uiso 0.500000 . 2
H16B H 0.7641(11) -0.1529(11) 0.5340(7) 0.047(2) Uiso 0.500000 R 2
C17B C 0.6649(12) -0.0611(10) 0.4227(6) 0.038(2) Uiso 0.500000 . 2
H17B H 0.7004(12) 0.0298(10) 0.4562(6) 0.046(3) Uiso 0.500000 R 2
C18B C 0.6762(12) -0.5288(9) 0.4280(6) 0.0453(19) Uiso 0.500000 . 2
H18d H 0.7236(12) -0.5827(9) 0.4761(6) 0.068(3) Uiso 0.500000 GR 2
H18e H 0.5371(12) -0.5700(9) 0.4004(6) 0.068(3) Uiso 0.500000 GR 2
H18f H 0.7419(12) -0.5286(9) 0.3771(6) 0.068(3) Uiso 0.500000 GR 2
O3B O 0.7131(8) -0.3937(7) 0.4715(4) 0.0444(14) Uiso 0.500000 . 2
C19 C 0.3946(5) -0.3528(3) 0.1174(2) 0.0335(7) Uani 1.000000 . .
H19c H 0.3943(5) -0.3311(3) 0.0520(2) 0.0402(8) Uiso 0.500000 R 2
H19d H 0.4962(5) -0.3976(3) 0.1387(2) 0.0402(8) Uiso 0.500000 R 2
H19a H 0.4934(5) -0.4003(3) 0.1376(2) 0.0402(8) Uiso 0.500000 R 1
H19b H 0.3921(5) -0.3346(3) 0.0511(2) 0.0402(8) Uiso 0.500000 R 1
C20 C 0.2019(6) -0.4478(4) 0.1163(3) 0.0488(9) Uani 1.000000 . .
H20a H 0.1743(6) -0.5331(4) 0.0723(3) 0.0732(14) Uiso 1.000000 R .
H20b H 0.2036(6) -0.4693(4) 0.1811(3) 0.0732(14) Uiso 1.000000 R .
H20c H 0.1020(6) -0.4031(4) 0.0947(3) 0.0732(14) Uiso 1.000000 R .
O1W O 0.8202(10) 0.2541(7) 0.3971(5) 0.0501(16) Uani 0.400000 . .
I1a I 0.3399(4) -0.3786(4) -0.1533(2) 0.0298(4) Uani 0.500000 . 1
N1a N 0.4578(11) -0.2103(8) 0.1853(6) 0.021(2) Uiso 0.500000 . 1
S1a S 0.4800(4) 0.0316(3) 0.2475(2) 0.0274(8) Uiso 0.500000 . 1


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
S1b C1 1.678(4) . ?
S1b C12B 1.774(9) . ?
O1 C6 1.356(4) . ?
O1 C10A 1.475(7) . ?
O1 C10B 1.450(6) . ?
O2 C7 1.358(4) . ?
O2 C11 1.427(4) . ?
N1b C1 1.408(8) . ?
N1b C13B 1.390(11) . ?
N1b C19 1.375(9) . ?
C1 C2 1.417(4) . ?
C1 N1a 1.280(8) . ?
C1 S1a 1.747(4) . ?
C2 C3 1.341(4) . ?
C3 C4 1.447(4) . ?
C4 C5 1.398(4) . ?
C4 C9 1.391(4) . ?
C5 C6 1.370(4) . ?
C6 C7 1.416(4) . ?
C7 C8 1.376(4) . ?
C8 C9 1.387(4) . ?
C12A C13A 1.373(11) . ?
C12A C17A 1.392(12) . ?
C12A S1a 1.694(8) . ?
C13A C14A 1.419(10) . ?
C13A N1a 1.395(11) . ?
C14A C15A 1.378(11) . ?
C15A C16A 1.388(12) . ?
C15A O3A 1.372(9) . ?
C16A C17A 1.373(12) . ?
C18A O3A 1.407(11) . ?
C12B C13B 1.372(12) . ?
C12B C17B 1.416(13) . ?
C13B C14B 1.377(10) . ?
C14B C15B 1.383(11) . ?
C15B C16B 1.391(12) . ?
C15B O3B 1.357(9) . ?
C16B C17B 1.383(13) . ?
C18B O3B 1.396(11) . ?
C19 C20 1.501(5) . ?
C19 N1a 1.578(9) . ?

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
C11 O2 C7 116.7(3) . . ?
C19 N1b C1 127.0(6) . . ?
N1b C1 S1b 113.1(4) . . ?
S1a C1 N1a 111.0(4) . . ?
C3 C2 C1 122.1(3) . . ?
C4 C3 C2 126.9(3) . . ?
C5 C4 C3 122.3(3) . . ?
C9 C4 C3 118.8(3) . . ?
C9 C4 C5 119.0(3) . . ?
C6 C5 C4 120.6(3) . . ?
C5 C6 O1 124.8(3) . . ?
C7 C6 O1 115.2(3) . . ?
C7 C6 C5 119.9(3) . . ?
C6 C7 O2 114.9(3) . . ?
C8 C7 O2 125.5(3) . . ?
C8 C7 C6 119.5(3) . . ?
C9 C8 C7 120.1(3) . . ?
C8 C9 C4 120.8(3) . . ?
C17A C12A C13A 120.9(8) . . ?
S1a C12A C13A 110.4(6) . . ?
S1a C12A C17A 128.6(7) . . ?
C14A C13A C12A 121.7(7) . . ?
N1a C13A C12A 112.2(7) . . ?
N1a C13A C14A 126.2(8) . . ?
C15A C14A C13A 116.2(8) . . ?
C16A C15A C14A 121.9(7) . . ?
O3A C15A C14A 122.8(8) . . ?
O3A C15A C16A 115.3(7) . . ?
C17A C16A C15A 121.5(8) . . ?
C16A C17A C12A 117.9(9) . . ?
C18A O3A C15A 119.0(7) . . ?
C13B C12B S1b 113.1(6) . . ?
C17B C12B S1b 125.1(8) . . ?
C17B C12B C13B 121.7(8) . . ?
C12B C13B N1b 110.7(7) . . ?
C14B C13B N1b 126.7(8) . . ?
C14B C13B C12B 122.6(8) . . ?
C15B C14B C13B 116.5(8) . . ?
C16B C15B C14B 121.6(7) . . ?
O3B C15B C14B 123.8(8) . . ?
O3B C15B C16B 114.6(7) . . ?
C17B C16B C15B 122.5(8) . . ?
C16B C17B C12B 115.1(9) . . ?
C18B O3B C15B 119.1(7) . . ?
C19 N1a C1 120.8(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p-1
_database_code_depnum_ccdc_archive 'CCDC 1056060'
_audit_update_record             
;
2015-03-25 deposited with the CCDC.
2015-05-18 downloaded from the CCDC.
;
_audit_creation_date             2015-01-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.19 svn.r3143 for OlexSys, GUI svn.r4992)
;
_chemical_formula_moiety         'I2, C40 H46 N O7 S2'
_chemical_formula_sum            'C40 H46 I2 N O7 S2'
_chemical_formula_weight         982.74
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
I -0.19193 6.94384 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03376 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.33536 0.55132 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.808(4)
_cell_length_b                   10.354(6)
_cell_length_c                   13.780(7)
_cell_angle_alpha                93.69(2)
_cell_angle_beta                 103.61(2)
_cell_angle_gamma                105.59(2)
_cell_volume                     1033.3(10)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    979
_cell_measurement_theta_max      54.712
_cell_measurement_theta_min      9.988
_exptl_absorpt_coefficient_mu    13.304
_exptl_absorpt_correction_T_max  0.9654
_exptl_absorpt_correction_T_min  0.3641
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.5792
_exptl_crystal_density_meas      .
_exptl_crystal_F_000             493.6866
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.005
_diffrn_reflns_av_R_equivalents  0.0846
_diffrn_reflns_av_unetI/netI     0.1684
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2646
_diffrn_reflns_theta_full        59.8358
_diffrn_reflns_theta_max         59.84
_diffrn_reflns_theta_min         9.99
_diffrn_ambient_temperature      103.15
_diffrn_measured_fraction_theta_full 0.6690
_diffrn_measured_fraction_theta_max 0.6690
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                1266
_reflns_number_total             2045
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.9329
_refine_diff_density_min         -1.7573
_refine_diff_density_rms         0.3287
_refine_ls_d_res_high            0.8916
_refine_ls_d_res_low             4.4448
_refine_ls_goodness_of_fit_ref   1.1164
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    35
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2045
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1565
_refine_ls_R_factor_gt           0.0871
_refine_ls_restrained_S_all      1.1164
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1902
_refine_ls_wR_factor_ref         0.2280
_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. Others
 Fixed Sof: O1W(0.5)
3.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C19(H19a,H19b)
3.c Me refined with riding coordinates:
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c), C18(H18a,H18b,H18c), C20(H20a,H20b,
 H20c)
3.d Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C9(H9), C14(H14), C16(H16), C17(H17)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
I1 I -0.2323(2) 0.10302(13) -0.17756(10) 0.0524(7) Uani 1.000000 .
S1 S 0.0479(8) 0.5316(5) 0.2422(4) 0.0524(17) Uani 1.000000 .
O1 O -0.6707(18) 0.3760(15) -0.2614(10) 0.056(4) Uani 1.000000 .
O2 O -0.677(2) 0.6217(16) -0.2884(13) 0.098(7) Uani 1.000000 .
O3 O 0.232(2) 0.1426(15) 0.5060(11) 0.067(5) Uani 1.000000 .
N1 N -0.010(2) 0.2833(16) 0.1791(11) 0.045(5) Uani 1.000000 .
C1 C -0.021(3) 0.4011(19) 0.1465(13) 0.036(5) Uiso 1.000000 .
C2 C -0.076(3) 0.419(2) 0.0403(14) 0.053(7) Uani 1.000000 .
H2 H -0.186(3) 0.344(2) 0.0017(14) 0.064(8) Uiso 1.000000 R
C3 C -0.096(3) 0.558(2) 0.0158(14) 0.054(7) Uani 1.000000 .
H3 H -0.057(3) 0.623(2) 0.0794(14) 0.065(8) Uiso 1.000000 R
C4 C -0.273(3) 0.569(2) -0.0497(13) 0.035(6) Uani 1.000000 .
C5 C -0.397(2) 0.4571(19) -0.1188(15) 0.038(6) Uani 1.000000 .
H5 H -0.384(2) 0.3691(19) -0.1146(15) 0.046(7) Uiso 1.000000 R
C6 C -0.544(3) 0.477(2) -0.1949(15) 0.050(6) Uani 1.000000 .
C7 C -0.546(3) 0.607(2) -0.2063(18) 0.051(7) Uani 1.000000 .
C8 C -0.430(3) 0.712(2) -0.1358(15) 0.045(6) Uani 1.000000 .
H8 H -0.443(3) 0.801(2) -0.1393(15) 0.054(7) Uiso 1.000000 R
C9 C -0.293(3) 0.691(2) -0.0591(15) 0.054(7) Uani 1.000000 .
H9 H -0.212(3) 0.766(2) -0.0121(15) 0.065(8) Uiso 1.000000 R
C10 C -0.690(3) 0.243(2) -0.2401(15) 0.059(7) Uani 1.000000 .
H10a H -0.786(3) 0.180(2) -0.2944(15) 0.089(11) Uiso 1.000000 R
H10b H -0.573(3) 0.222(2) -0.2345(15) 0.089(11) Uiso 1.000000 R
H10c H -0.724(3) 0.234(2) -0.1763(15) 0.089(11) Uiso 1.000000 R
C11 C -0.631(3) 0.735(2) -0.3385(15) 0.064(8) Uani 1.000000 .
H11a H -0.736(3) 0.732(2) -0.3949(15) 0.096(11) Uiso 1.000000 R
H11b H -0.601(3) 0.818(2) -0.2914(15) 0.096(11) Uiso 1.000000 R
H11c H -0.524(3) 0.734(2) -0.3642(15) 0.096(11) Uiso 1.000000 R
C12 C 0.100(3) 0.4292(19) 0.3330(15) 0.040(6) Uani 1.000000 .
C13 C 0.061(3) 0.295(2) 0.2864(14) 0.043(6) Uani 1.000000 .
C14 C 0.101(3) 0.1932(19) 0.3390(14) 0.041(6) Uani 1.000000 .
H14 H 0.079(3) 0.1042(19) 0.3066(14) 0.049(7) Uiso 1.000000 R
C15 C 0.176(3) 0.228(2) 0.4412(15) 0.064(8) Uani 1.000000 .
C16 C 0.213(3) 0.363(2) 0.4897(17) 0.064(7) Uani 1.000000 .
H16 H 0.268(3) 0.385(2) 0.5602(17) 0.077(9) Uiso 1.000000 R
C17 C 0.170(3) 0.458(2) 0.4346(15) 0.054(7) Uani 1.000000 .
H17 H 0.189(3) 0.547(2) 0.4672(15) 0.064(8) Uiso 1.000000 R
C18 C 0.213(3) 0.010(2) 0.4656(16) 0.058(7) Uani 1.000000 .
H18a H 0.258(3) -0.039(2) 0.5199(16) 0.087(11) Uiso 1.000000 R
H18b H 0.083(3) -0.036(2) 0.4326(16) 0.087(11) Uiso 1.000000 R
H18c H 0.286(3) 0.013(2) 0.4161(16) 0.087(11) Uiso 1.000000 R
C19 C -0.072(3) 0.1513(16) 0.1141(14) 0.047(6) Uani 1.000000 .
H19a H -0.076(3) 0.1673(16) 0.0437(14) 0.056(8) Uiso 1.000000 R
H19b H 0.019(3) 0.1014(16) 0.1352(14) 0.056(8) Uiso 1.000000 R
C20 C -0.255(3) 0.066(2) 0.1179(15) 0.051(6) Uani 1.000000 .
H20a H -0.289(3) -0.020(2) 0.0735(15) 0.077(10) Uiso 1.000000 R
H20b H -0.252(3) 0.048(2) 0.1872(15) 0.077(10) Uiso 1.000000 R
H20c H -0.347(3) 0.114(2) 0.0956(15) 0.077(10) Uiso 1.000000 R
O1W O -0.354(3) 0.241(2) -0.4044(15) 0.031(7) Uani 0.500000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.703(19) . ?
S1 C12 1.737(19) . ?
O1 C6 1.34(2) . ?
O1 C10 1.40(2) . ?
O2 C7 1.38(2) . ?
O2 C11 1.41(2) . ?
O3 C15 1.38(2) . ?
O3 C18 1.41(2) . ?
N1 C1 1.34(2) . ?
N1 C13 1.44(2) . ?
N1 C19 1.48(2) . ?
C1 C2 1.46(2) . ?
C2 H2 1.0000 . ?
C2 C3 1.53(3) . ?
C2 C3 1.68(3) 2_565 ?
C3 H3 1.0000 . ?
C3 C4 1.50(3) . ?
C4 C5 1.42(2) . ?
C4 C9 1.33(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.43(2) . ?
C6 C7 1.37(3) . ?
C7 C8 1.37(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.39(3) . ?
C9 H9 0.9500 . ?
C10 H10a 0.9800 . ?
C10 H10b 0.9800 . ?
C10 H10c 0.9800 . ?
C11 H11a 0.9800 . ?
C11 H11b 0.9800 . ?
C11 H11c 0.9800 . ?
C12 C13 1.42(3) . ?
C12 C17 1.36(2) . ?
C13 C14 1.38(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.37(2) . ?
C15 C16 1.43(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.35(3) . ?
C17 H17 0.9500 . ?
C18 H18a 0.9800 . ?
C18 H18b 0.9800 . ?
C18 H18c 0.9800 . ?
C19 H19a 0.9900 . ?
C19 H19b 0.9900 . ?
C19 C20 1.48(3) . ?
C20 H20a 0.9800 . ?
C20 H20b 0.9800 . ?
C20 H20c 0.9800 . ?

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
C12 S1 C1 92.7(10) . . ?
C10 O1 C6 118.1(15) . . ?
C11 O2 C7 118.3(15) . . ?
C18 O3 C15 118.4(16) . . ?
C13 N1 C1 113.4(16) . . ?
C19 N1 C1 124.8(14) . . ?
C19 N1 C13 121.7(16) . . ?
N1 C1 S1 112.7(13) . . ?
C2 C1 S1 122.7(15) . . ?
C2 C1 N1 124.5(17) . . ?
H2 C2 C1 111.5(11) . . ?
C3 C2 C1 118.0(18) . . ?
C3 C2 C1 113.4(17) 2_565 . ?
C3 C2 H2 111.5(11) . . ?
C3 C2 H2 111.5(9) 2_565 . ?
H3 C3 C2 109.9(10) . . ?
H3 C3 C2 109.9(9) . 2_565 ?
C4 C3 C2 120.5(18) . . ?
C4 C3 C2 114.2(16) . 2_565 ?
C4 C3 H3 109.9(10) . . ?
C5 C4 C3 120.9(17) . . ?
C9 C4 C3 118.5(17) . . ?
C9 C4 C5 118.9(17) . . ?
H5 C5 C4 120.1(11) . . ?
C6 C5 C4 119.7(18) . . ?
C6 C5 H5 120.1(12) . . ?
C5 C6 O1 123.3(19) . . ?
C7 C6 O1 118.2(18) . . ?
C7 C6 C5 118.1(18) . . ?
C6 C7 O2 115.7(19) . . ?
C8 C7 O2 124(2) . . ?
C8 C7 C6 120.1(19) . . ?
H8 C8 C7 119.6(12) . . ?
C9 C8 C7 121(2) . . ?
C9 C8 H8 119.6(13) . . ?
C8 C9 C4 121.5(19) . . ?
H9 C9 C4 119.2(11) . . ?
H9 C9 C8 119.2(13) . . ?
H10a C10 O1 109.5 . . ?
H10b C10 O1 109.5 . . ?
H10b C10 H10a 109.5 . . ?
H10c C10 O1 109.5 . . ?
H10c C10 H10a 109.5 . . ?
H10c C10 H10b 109.5 . . ?
H11a C11 O2 109.5 . . ?
H11b C11 O2 109.5 . . ?
H11b C11 H11a 109.5 . . ?
H11c C11 O2 109.5 . . ?
H11c C11 H11a 109.5 . . ?
H11c C11 H11b 109.5 . . ?
C13 C12 S1 109.8(14) . . ?
C17 C12 S1 131.1(17) . . ?
C17 C12 C13 119.1(18) . . ?
C12 C13 N1 111.4(17) . . ?
C14 C13 N1 125.7(19) . . ?
C14 C13 C12 122.7(18) . . ?
H14 C14 C13 122.0(12) . . ?
C15 C14 C13 116.0(19) . . ?
C15 C14 H14 122.0(14) . . ?
C14 C15 O3 125(2) . . ?
C16 C15 O3 113.2(17) . . ?
C16 C15 C14 122(2) . . ?
H16 C16 C15 120.2(12) . . ?
C17 C16 C15 120(2) . . ?
C17 C16 H16 120.2(13) . . ?
C16 C17 C12 121(2) . . ?
H17 C17 C12 119.7(13) . . ?
H17 C17 C16 119.7(13) . . ?
H18a C18 O3 109.5 . . ?
H18b C18 O3 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 O3 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 109.5 . . ?
H19a C19 N1 108.9(10) . . ?
H19b C19 N1 108.9(10) . . ?
H19b C19 H19a 107.7 . . ?
C20 C19 N1 113.4(19) . . ?
C20 C19 H19a 108.9(10) . . ?
C20 C19 H19b 108.9(11) . . ?
H20a C20 C19 109.5 . . ?
H20b C20 C19 109.5 . . ?
H20b C20 H20a 109.5 . . ?
H20c C20 C19 109.5 . . ?
H20c C20 H20a 109.5 . . ?
H20c C20 H20b 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p-1
_database_code_depnum_ccdc_archive 'CCDC 1056061'
_audit_update_record             
;
2015-03-25 deposited with the CCDC.
2015-05-18 downloaded from the CCDC.
;
_audit_creation_date             2015-01-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.19 svn.r3143 for OlexSys, GUI svn.r4992)
;
_chemical_formula_moiety         'I, C20 H16 N O3 S, 0.5(O)'
_chemical_formula_sum            'C20 H16 I N O3.5 S'
_chemical_formula_weight         485.33
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.564(4)
_cell_length_b                   10.338(5)
_cell_length_c                   14.496(7)
_cell_angle_alpha                93.619(5)
_cell_angle_beta                 104.077(5)
_cell_angle_gamma                105.686(5)
_cell_volume                     1048.4(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6820
_cell_measurement_theta_max      27.538
_cell_measurement_theta_min      2.789
_exptl_absorpt_coefficient_mu    1.647
_exptl_absorpt_correction_T_max  0.9921
_exptl_absorpt_correction_T_min  0.9803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1340 before and 0.0849 after correction.
The Ratio of minimum to maximum transmission is 0.7732.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellowish
_exptl_crystal_colour_primary    yellowish
_exptl_crystal_density_diffrn    1.5372
_exptl_crystal_density_meas      .
_exptl_crystal_description       needle
_exptl_crystal_F_000             479.6267
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.005
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.0859
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8048
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         28.49
_diffrn_reflns_theta_min         2.07
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.8850
_diffrn_measured_fraction_theta_max 0.8564
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -10
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                3915
_reflns_number_total             5306
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         2.1443
_refine_diff_density_min         -2.5322
_refine_diff_density_rms         0.2422
_refine_ls_d_res_high            0.7450
_refine_ls_d_res_low             9.8577
_refine_ls_goodness_of_fit_ref   1.0319
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    24
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4544
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0696
_refine_ls_restrained_S_all      1.0319
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0000P)²+13.9291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1629
_refine_ls_wR_factor_ref         0.1682
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: S1a(0.7) N1a(0.7) C1a(0.7) C2(0.7) C3(0.7) C4a(0.7) S1b(0.3)
 N1b(0.3) C1b(0.3) C2'(0.3) C3'(0.3) C4b(0.3) O1W(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C14(H14), C16(H16), C17(H17)
3.b Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c), C18(H18a,H18b,H18c), C20(H20a,H20b,
 H20c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
_atom_site_disorder_group
I1 I 0.19278(8) 0.88574(5) 0.66693(4) 0.02770(16) Uani 1.000000 . .
O1 O -0.6265(9) 0.3665(5) 0.2076(4) 0.0345(13) Uani 1.000000 . .
O2 O -0.6077(10) 0.6132(6) 0.1753(4) 0.0415(15) Uani 1.000000 . .
O3 O 0.2339(11) 0.1434(7) 0.9897(4) 0.0477(16) Uani 1.000000 . .
S1a S -0.0000(5) 0.5252(4) 0.7480(3) 0.0271(9) Uiso 0.700000 . 1
N1a N -0.0509(18) 0.2769(12) 0.6846(9) 0.020(3) Uiso 0.700000 . 1
C1a C -0.0865(15) 0.3905(11) 0.6572(8) 0.018(2) Uiso 0.700000 . 1
C2 C -0.1859(14) 0.4030(10) 0.5616(6) 0.0188(17) Uiso 0.700000 . 1
C3 C -0.2123(13) 0.5222(9) 0.5378(6) 0.0183(17) Uiso 0.700000 . 1
C4a C -0.3193(17) 0.5446(12) 0.4437(8) 0.017(3) Uiso 0.700000 . 1
S1b S 0.0110(12) 0.5300(9) 0.7288(7) 0.029(2) Uiso 0.300000 . 2
N1b N -0.032(4) 0.283(3) 0.671(2) 0.020(7) Uiso 0.300000 . 2
C1b C -0.062(3) 0.394(2) 0.6332(18) 0.015(5) Uiso 0.300000 . 2
C2' C -0.089(3) 0.414(2) 0.5304(16) 0.023(4) Uiso 0.300000 . 2
C3' C -0.098(3) 0.561(2) 0.5056(16) 0.023(4) Uiso 0.300000 . 2
C4b C -0.287(4) 0.562(3) 0.430(2) 0.023(7) Uiso 0.300000 . 2
C5 C -0.4144(11) 0.4412(7) 0.3681(5) 0.0251(14) Uani 1.000000 . .
C6 C -0.5171(11) 0.4652(7) 0.2816(5) 0.0256(14) Uani 1.000000 . .
C7 C -0.5110(12) 0.6013(8) 0.2646(5) 0.0281(15) Uani 1.000000 . .
C8 C -0.4112(11) 0.7071(8) 0.3379(5) 0.0274(15) Uani 1.000000 . .
H8 H -0.4101(11) 0.7954(8) 0.3282(5) 0.0329(18) Uiso 1.000000 R .
C9 C -0.3127(10) 0.6827(7) 0.4258(5) 0.0247(14) Uani 1.000000 . .
C10 C -0.6816(13) 0.2292(8) 0.2297(6) 0.0372(19) Uani 1.000000 . .
H10a H -0.776(7) 0.1719(16) 0.1753(19) 0.056(3) Uiso 1.000000 GR .
H10b H -0.572(2) 0.197(3) 0.244(5) 0.056(3) Uiso 1.000000 GR .
H10c H -0.733(9) 0.2280(14) 0.284(3) 0.056(3) Uiso 1.000000 GR .
C11 C -0.6031(13) 0.7477(8) 0.1547(6) 0.0352(18) Uani 1.000000 . .
H11a H -0.665(8) 0.7443(11) 0.0881(13) 0.053(3) Uiso 1.000000 GR .
H11b H -0.668(8) 0.786(3) 0.194(4) 0.053(3) Uiso 1.000000 GR .
H11c H -0.4730(13) 0.8031(19) 0.169(4) 0.053(3) Uiso 1.000000 GR .
C12 C 0.0781(13) 0.4261(9) 0.8259(6) 0.0352(18) Uani 1.000000 . .
C13 C 0.0385(11) 0.2916(8) 0.7799(5) 0.0266(15) Uani 1.000000 . .
C14 C 0.0899(12) 0.1908(9) 0.8307(5) 0.0315(17) Uani 1.000000 . .
H14 H 0.0680(12) 0.1036(9) 0.8007(5) 0.038(2) Uiso 1.000000 R .
C15 C 0.1767(16) 0.2288(10) 0.9297(6) 0.045(2) Uani 1.000000 . .
C16 C 0.2086(17) 0.3595(10) 0.9758(6) 0.051(3) Uani 1.000000 . .
H16 H 0.2624(17) 0.3795(10) 1.0419(6) 0.062(3) Uiso 1.000000 R .
C17 C 0.1617(17) 0.4583(10) 0.9250(6) 0.048(2) Uani 1.000000 . .
H17 H 0.1851(17) 0.5453(10) 0.9559(6) 0.058(3) Uiso 1.000000 R .
C18 C 0.2136(14) 0.0095(10) 0.9505(6) 0.042(2) Uani 1.000000 . .
H18a H 0.275(9) 0.0124(10) 0.900(3) 0.063(3) Uiso 1.000000 GR .
H18b H 0.272(9) -0.036(3) 0.9997(14) 0.063(3) Uiso 1.000000 GR .
H18c H 0.0806(14) -0.039(2) 0.926(5) 0.063(3) Uiso 1.000000 GR .
C19 C -0.0959(12) 0.1485(7) 0.6163(5) 0.0271(15) Uani 1.000000 . .
C20 C -0.2896(12) 0.0570(8) 0.6161(6) 0.0326(17) Uani 1.000000 . .
H20a H -0.318(4) -0.027(3) 0.575(4) 0.049(2) Uiso 1.000000 GR .
H20b H -0.289(3) 0.038(5) 0.6802(9) 0.049(2) Uiso 1.000000 GR .
H20c H -0.3851(17) 0.101(3) 0.593(4) 0.049(2) Uiso 1.000000 GR .
O1W O 0.3319(15) 0.7586(10) 0.8942(7) 0.025(2) Uani 0.500000 . .


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
O1 C6 1.360(9) . ?
O1 C10 1.447(9) . ?
O2 C7 1.355(9) . ?
O2 C11 1.433(9) . ?
O3 C15 1.359(11) . ?
O3 C18 1.416(12) . ?
S1a C1a 1.720(12) . ?
S1a C12 1.680(9) . ?
N1a C1a 1.336(16) . ?
N1a C13 1.360(14) . ?
N1a C19 1.512(14) . ?
C1a C2 1.439(14) . ?
C2 C3 1.353(13) . ?
C3 C4a 1.474(14) . ?
C4a C5 1.383(13) . ?
C4a C9 1.456(14) . ?
S1b C1b 1.78(3) . ?
S1b C12 1.879(12) . ?
N1b C1b 1.35(4) . ?
N1b C13 1.53(3) . ?
N1b C19 1.45(3) . ?
C1b C2' 1.49(3) . ?
C2' C3' 1.60(3) . ?
C2' C3' 1.58(3) 2_566 ?
C3' C4b 1.58(4) . ?
C4b C5 1.44(3) . ?
C4b C9 1.32(3) . ?
C5 C6 1.382(9) . ?
C6 C7 1.434(10) . ?
C7 C8 1.383(11) . ?
C8 H8 0.9300 . ?
C8 C9 1.387(10) . ?
C10 H10a 0.9600 . ?
C10 H10b 0.9600 . ?
C10 H10c 0.9600 . ?
C11 H11a 0.9600 . ?
C11 H11b 0.9600 . ?
C11 H11c 0.9600 . ?
C12 C13 1.424(11) . ?
C12 C17 1.399(12) . ?
C13 C14 1.399(10) . ?
C14 H14 0.9300 . ?
C14 C15 1.406(12) . ?
C15 C16 1.400(14) . ?
C16 H16 0.9300 . ?
C16 C17 1.369(14) . ?
C17 H17 0.9300 . ?
C18 H18a 0.9600 . ?
C18 H18b 0.9600 . ?
C18 H18c 0.9600 . ?
C19 C20 1.513(11) . ?
C20 H20a 0.9600 . ?
C20 H20b 0.9600 . ?
C20 H20c 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
C10 O1 C6 117.1(5) . . ?
C11 O2 C7 116.9(6) . . ?
C18 O3 C15 118.7(7) . . ?
C19 N1a C13 123.7(9) . . ?
N1a C1a S1a 113.5(9) . . ?
C2 C1a S1a 121.8(8) . . ?
C2 C1a N1a 124.8(10) . . ?
C3 C2 C1a 121.8(9) . . ?
C4a C3 C2 126.2(9) . . ?
C9 C4a C5 117.7(9) . . ?
C19 N1b C13 116.2(19) . . ?
N1b C1b S1b 108.0(19) . . ?
C2' C1b S1b 123.3(17) . . ?
C2' C1b N1b 126(2) . . ?
C3' C2' C1b 116.5(19) . . ?
C3' C2' C1b 115.0(19) 2_566 . ?
C4b C3' C2' 115(2) . . ?
C4b C3' C2' 117.1(19) . 2_566 ?
C9 C4b C5 123(2) . . ?
C5 C6 O1 124.3(6) . . ?
C7 C6 O1 115.5(6) . . ?
C7 C6 C5 120.2(7) . . ?
C6 C7 O2 115.0(7) . . ?
C8 C7 O2 125.7(7) . . ?
C8 C7 C6 119.2(6) . . ?
H8 C8 C7 119.7(4) . . ?
C9 C8 C7 120.5(7) . . ?
C9 C8 H8 119.7(4) . . ?
H10a C10 O1 109.5 . . ?
H10b C10 O1 109.5 . . ?
H10b C10 H10a 109.5 . . ?
H10c C10 O1 109.5 . . ?
H10c C10 H10a 109.5 . . ?
H10c C10 H10b 109.5 . . ?
H11a C11 O2 109.5 . . ?
H11b C11 O2 109.5 . . ?
H11b C11 H11a 109.5 . . ?
H11c C11 O2 109.5 . . ?
H11c C11 H11a 109.5 . . ?
H11c C11 H11b 109.5 . . ?
C17 C12 C13 120.1(8) . . ?
C14 C13 C12 121.4(7) . . ?
H14 C14 C13 121.9(4) . . ?
C15 C14 C13 116.2(8) . . ?
C15 C14 H14 121.9(5) . . ?
C14 C15 O3 123.9(8) . . ?
C16 C15 O3 113.8(8) . . ?
C16 C15 C14 122.4(8) . . ?
H16 C16 C15 119.5(5) . . ?
C17 C16 C15 120.9(9) . . ?
C17 C16 H16 119.5(5) . . ?
C16 C17 C12 118.9(8) . . ?
H17 C17 C12 120.6(5) . . ?
H17 C17 C16 120.6(5) . . ?
H18a C18 O3 109.5 . . ?
H18b C18 O3 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 O3 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 109.5 . . ?
H20a C20 C19 109.5 . . ?
H20b C20 C19 109.5 . . ?
H20b C20 H20a 109.5 . . ?
H20c C20 C19 109.5 . . ?
H20c C20 H20a 109.5 . . ?
H20c C20 H20b 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
