# Electronic Supplementary Material (ESI) for ChemComm.
# 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. 
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data_1_NIS
_database_code_depnum_ccdc_archive 'CCDC 1426136'
_audit_update_record             
;
2015-09-21 deposited with the CCDC.
2015-12-15 downloaded from the CCDC.
;
_audit_creation_date             2015-03-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C9 H9 I N2 O3'
_chemical_formula_sum            'C9 H9 I N2 O3'
_chemical_formula_weight         320.08
_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'

_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                   8.1540(16)
_cell_length_b                   11.633(2)
_cell_length_c                   12.467(3)
_cell_angle_alpha                67.55(3)
_cell_angle_beta                 76.11(3)
_cell_angle_gamma                76.47(3)
_cell_volume                     1047.5(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    170
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.046
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0642 before and 0.0441 after correction.
The Ratio of minimum to maximum transmission is 0.7868.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.030
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8919
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.245
_diffrn_reflns_theta_min         2.606
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3465
_reflns_number_total             3754
_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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3754
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0210
_refine_ls_R_factor_gt           0.0187
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+1.2304P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0415
_refine_ls_wR_factor_ref         0.0425
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.56278(2) 0.19005(2) 0.74137(2) 0.01567(6) Uani 1 1 d . . . . .
O1 O 0.7427(2) 0.06280(16) 0.62475(18) 0.0220(4) Uani 1 1 d . . . . .
O2 O 0.3643(2) 0.13809(16) 1.01572(17) 0.0210(4) Uani 1 1 d . . . . .
O3 O 0.4491(2) 0.49641(16) 0.70078(18) 0.0235(4) Uani 1 1 d . . . . .
N1 N 0.6883(2) -0.03171(19) 0.6142(2) 0.0163(5) Uani 1 1 d . . . . .
N2 N 0.4221(2) 0.30052(18) 0.84123(19) 0.0148(4) Uani 1 1 d . . . . .
C1 C 0.6036(3) -0.1130(2) 0.7086(3) 0.0201(6) Uani 1 1 d . . . . .
H1 H 0.5794 -0.1024 0.7830 0.024 Uiso 1 1 calc R . . . .
C2 C 0.5522(3) -0.2118(2) 0.6961(3) 0.0230(6) Uani 1 1 d . . . . .
H2 H 0.4904 -0.2684 0.7617 0.028 Uiso 1 1 calc R . . . .
C3 C 0.5906(3) -0.2280(2) 0.5886(3) 0.0256(7) Uani 1 1 d . . . . .
H3 H 0.5572 -0.2965 0.5797 0.031 Uiso 1 1 calc R . . . .
C4 C 0.6780(3) -0.1438(2) 0.4939(3) 0.0241(6) Uani 1 1 d . . . . .
H4 H 0.7050 -0.1535 0.4191 0.029 Uiso 1 1 calc R . . . .
C5 C 0.7259(3) -0.0458(2) 0.5083(3) 0.0215(6) Uani 1 1 d . . . . .
H5 H 0.7859 0.0125 0.4431 0.026 Uiso 1 1 calc R . . . .
C6 C 0.3995(3) 0.4313(2) 0.8001(2) 0.0169(5) Uani 1 1 d . . . . .
C7 C 0.3045(3) 0.4761(2) 0.9004(3) 0.0229(6) Uani 1 1 d . . . . .
H7A H 0.1926 0.5273 0.8826 0.027 Uiso 1 1 calc R . . . .
H7B H 0.3719 0.5276 0.9151 0.027 Uiso 1 1 calc R . . . .
C8 C 0.2800(3) 0.3565(2) 1.0070(3) 0.0216(6) Uani 1 1 d . . . . .
H8A H 0.3394 0.3517 1.0696 0.026 Uiso 1 1 calc R . . . .
H8B H 0.1570 0.3541 1.0395 0.026 Uiso 1 1 calc R . . . .
C9 C 0.3577(3) 0.2501(2) 0.9602(2) 0.0166(5) Uani 1 1 d . . . . .
I2 I 0.86786(2) 0.39793(2) 0.84356(2) 0.01565(6) Uani 1 1 d . . . . .
O4 O 0.6877(2) 0.27247(15) 1.01654(17) 0.0207(4) Uani 1 1 d . . . . .
O5 O 0.9766(2) 0.68779(16) 0.73054(18) 0.0242(4) Uani 1 1 d . . . . .
O6 O 1.1232(2) 0.34356(18) 0.6164(2) 0.0305(5) Uani 1 1 d . . . . .
N3 N 0.7791(2) 0.16406(18) 1.0749(2) 0.0170(5) Uani 1 1 d . . . . .
N4 N 1.0230(3) 0.50173(19) 0.6944(2) 0.0168(5) Uani 1 1 d . . . . .
C10 C 0.7597(3) 0.0548(2) 1.0682(2) 0.0183(6) Uani 1 1 d . . . . .
H10 H 0.6844 0.0548 1.0208 0.022 Uiso 1 1 calc R . . . .
C11 C 0.8507(3) -0.0566(2) 1.1312(3) 0.0228(6) Uani 1 1 d . . . . .
H11 H 0.8373 -0.1338 1.1271 0.027 Uiso 1 1 calc R . . . .
C12 C 0.9611(3) -0.0576(3) 1.2000(3) 0.0240(6) Uani 1 1 d . . . . .
H12 H 1.0232 -0.1346 1.2437 0.029 Uiso 1 1 calc R . . . .
C13 C 0.9792(3) 0.0557(3) 1.2040(3) 0.0248(6) Uani 1 1 d . . . . .
H13 H 1.0556 0.0576 1.2498 0.030 Uiso 1 1 calc R . . . .
C14 C 0.8864(3) 0.1658(2) 1.1413(3) 0.0207(6) Uani 1 1 d . . . . .
H14 H 0.8978 0.2437 1.1449 0.025 Uiso 1 1 calc R . . . .
C15 C 1.1202(3) 0.4509(2) 0.6104(3) 0.0200(6) Uani 1 1 d . . . . .
C16 C 1.2173(3) 0.5489(2) 0.5159(3) 0.0227(6) Uani 1 1 d . . . . .
H16A H 1.1944 0.5620 0.4373 0.027 Uiso 1 1 calc R . . . .
H16B H 1.3419 0.5237 0.5162 0.027 Uiso 1 1 calc R . . . .
C17 C 1.1507(3) 0.6681(2) 0.5474(3) 0.0234(6) Uani 1 1 d . . . . .
H17A H 1.2467 0.7050 0.5502 0.028 Uiso 1 1 calc R . . . .
H17B H 1.0824 0.7317 0.4888 0.028 Uiso 1 1 calc R . . . .
C18 C 1.0410(3) 0.6264(2) 0.6668(2) 0.0180(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 O1 2.4619(19) . ?
I1 N2 2.089(2) . ?
O1 N1 1.338(3) . ?
O2 C9 1.214(3) . ?
O3 C6 1.207(3) . ?
N1 C1 1.350(3) . ?
N1 C5 1.346(4) . ?
N2 C6 1.389(3) . ?
N2 C9 1.388(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.384(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.376(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.372(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.510(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.527(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.511(3) . ?
I2 O4 2.453(2) . ?
I2 N4 2.094(2) . ?
O4 N3 1.340(3) . ?
O5 C18 1.215(3) . ?
O6 C15 1.217(3) . ?
N3 C10 1.352(3) . ?
N3 C14 1.349(3) . ?
N4 C15 1.389(3) . ?
N4 C18 1.392(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.378(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.380(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.374(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.504(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.527(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.504(4) . ?

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
N2 I1 O1 176.91(7) . . ?
N1 O1 I1 121.83(14) . . ?
O1 N1 C1 120.5(2) . . ?
O1 N1 C5 118.2(2) . . ?
C5 N1 C1 121.3(2) . . ?
C6 N2 I1 123.98(17) . . ?
C9 N2 I1 122.99(16) . . ?
C9 N2 C6 112.7(2) . . ?
N1 C1 H1 120.3 . . ?
N1 C1 C2 119.4(3) . . ?
C2 C1 H1 120.3 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0(3) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.2(2) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 120.4(3) . . ?
N1 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
O3 C6 N2 125.0(2) . . ?
O3 C6 C7 126.6(2) . . ?
N2 C6 C7 108.3(2) . . ?
C6 C7 H7A 110.7 . . ?
C6 C7 H7B 110.7 . . ?
C6 C7 C8 105.4(2) . . ?
H7A C7 H7B 108.8 . . ?
C8 C7 H7A 110.7 . . ?
C8 C7 H7B 110.7 . . ?
C7 C8 H8A 110.8 . . ?
C7 C8 H8B 110.8 . . ?
H8A C8 H8B 108.9 . . ?
C9 C8 C7 104.6(2) . . ?
C9 C8 H8A 110.8 . . ?
C9 C8 H8B 110.8 . . ?
O2 C9 N2 124.5(2) . . ?
O2 C9 C8 126.7(3) . . ?
N2 C9 C8 108.9(2) . . ?
N4 I2 O4 178.71(7) . . ?
N3 O4 I2 111.01(13) . . ?
O4 N3 C10 119.6(2) . . ?
O4 N3 C14 119.2(2) . . ?
C14 N3 C10 121.2(2) . . ?
C15 N4 I2 122.21(16) . . ?
C15 N4 C18 112.4(2) . . ?
C18 N4 I2 125.41(17) . . ?
N3 C10 H10 120.4 . . ?
N3 C10 C11 119.2(2) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.8(2) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 120.7 . . ?
C11 C12 C13 118.5(3) . . ?
C13 C12 H12 120.7 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.8(3) . . ?
C14 C13 H13 120.1 . . ?
N3 C14 C13 120.4(2) . . ?
N3 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
O6 C15 N4 123.6(2) . . ?
O6 C15 C16 127.6(3) . . ?
N4 C15 C16 108.9(2) . . ?
C15 C16 H16A 110.9 . . ?
C15 C16 H16B 110.9 . . ?
C15 C16 C17 104.5(2) . . ?
H16A C16 H16B 108.9 . . ?
C17 C16 H16A 110.9 . . ?
C17 C16 H16B 110.9 . . ?
C16 C17 H17A 110.7 . . ?
C16 C17 H17B 110.7 . . ?
H17A C17 H17B 108.8 . . ?
C18 C17 C16 105.3(2) . . ?
C18 C17 H17A 110.7 . . ?
C18 C17 H17B 110.7 . . ?
O5 C18 N4 124.1(2) . . ?
O5 C18 C17 127.7(2) . . ?
N4 C18 C17 108.2(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 O1 N1 C1 -42.8(3) . . . . ?
I1 O1 N1 C5 139.59(18) . . . . ?
I1 N2 C6 O3 4.6(4) . . . . ?
I1 N2 C6 C7 -175.06(16) . . . . ?
I1 N2 C9 O2 -6.0(3) . . . . ?
I1 N2 C9 C8 173.95(15) . . . . ?
O1 N1 C1 C2 -178.4(2) . . . . ?
O1 N1 C5 C4 177.8(2) . . . . ?
O3 C6 C7 C8 -177.4(2) . . . . ?
N1 C1 C2 C3 1.3(4) . . . . ?
N2 C6 C7 C8 2.3(3) . . . . ?
C1 N1 C5 C4 0.2(4) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 N1 0.2(4) . . . . ?
C5 N1 C1 C2 -0.9(4) . . . . ?
C6 N2 C9 O2 -179.3(2) . . . . ?
C6 N2 C9 C8 0.7(3) . . . . ?
C6 C7 C8 C9 -1.8(3) . . . . ?
C7 C8 C9 O2 -179.3(2) . . . . ?
C7 C8 C9 N2 0.7(3) . . . . ?
C9 N2 C6 O3 177.7(2) . . . . ?
C9 N2 C6 C7 -1.9(3) . . . . ?
I2 O4 N3 C10 -106.4(2) . . . . ?
I2 O4 N3 C14 75.0(2) . . . . ?
I2 N4 C15 O6 0.0(4) . . . . ?
I2 N4 C15 C16 -179.51(16) . . . . ?
I2 N4 C18 O5 5.0(4) . . . . ?
I2 N4 C18 C17 -174.80(17) . . . . ?
O4 N3 C10 C11 -178.2(2) . . . . ?
O4 N3 C14 C13 178.7(2) . . . . ?
O6 C15 C16 C17 174.5(3) . . . . ?
N3 C10 C11 C12 -0.3(4) . . . . ?
N4 C15 C16 C17 -6.0(3) . . . . ?
C10 N3 C14 C13 0.1(4) . . . . ?
C10 C11 C12 C13 -0.4(4) . . . . ?
C11 C12 C13 C14 0.9(4) . . . . ?
C12 C13 C14 N3 -0.8(4) . . . . ?
C14 N3 C10 C11 0.4(4) . . . . ?
C15 N4 C18 O5 -175.4(2) . . . . ?
C15 N4 C18 C17 4.8(3) . . . . ?
C15 C16 C17 C18 8.5(3) . . . . ?
C16 C17 C18 O5 171.9(3) . . . . ?
C16 C17 C18 N4 -8.3(3) . . . . ?
C18 N4 C15 O6 -179.6(3) . . . . ?
C18 N4 C15 C16 0.9(3) . . . . ?

_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_2_NIS
_database_code_depnum_ccdc_archive 'CCDC 1426137'
_audit_update_record             
;
2015-09-21 deposited with the CCDC.
2015-12-15 downloaded from the CCDC.
;
_audit_creation_date             2015-07-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C10 H11 I N2 O3), H2 O'
_chemical_formula_sum            'C20 H24 I2 N4 O7'
_chemical_formula_weight         686.23
_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'

_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                   9.7294(19)
_cell_length_b                   11.427(2)
_cell_length_c                   11.566(2)
_cell_angle_alpha                90.02(3)
_cell_angle_beta                 110.88(3)
_cell_angle_gamma                93.06(3)
_cell_volume                     1199.4(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    170
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.670
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0712 before and 0.0540 after correction.
The Ratio of minimum to maximum transmission is 0.8132.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.900
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             668
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12583
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.249
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_min         1.785
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3893
_reflns_number_total             4354
_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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4354
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0229
_refine_ls_restrained_S_all      1.044
_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)+1.7921P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0479
_refine_ls_wR_factor_ref         0.0494
_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,H) groups
2.a Free rotating group:
 O7(H7A,H7B)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C18(H18A,H18B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.74709(2) 0.47848(2) 0.61104(2) 0.02033(6) Uani 1 1 d . . . . .
O1 O 0.9032(3) 0.64449(19) 0.7109(2) 0.0307(6) Uani 1 1 d . . . . .
O2 O 0.4738(2) 0.3144(2) 0.6518(2) 0.0279(5) Uani 1 1 d . . . . .
O3 O 0.6888(3) 0.3148(2) 0.3604(2) 0.0314(6) Uani 1 1 d . . . . .
N1 N 1.0038(3) 0.6239(2) 0.8216(2) 0.0232(6) Uani 1 1 d . . . . .
N2 N 0.6038(3) 0.3357(2) 0.5205(2) 0.0189(5) Uani 1 1 d . . . . .
C1 C 1.1227(4) 0.5645(3) 0.8282(3) 0.0275(8) Uani 1 1 d . . . . .
H1 H 1.1321 0.5360 0.7544 0.033 Uiso 1 1 calc R . . . .
C2 C 1.2294(4) 0.5451(3) 0.9399(3) 0.0310(8) Uani 1 1 d . . . . .
H2 H 1.3124 0.5027 0.9440 0.037 Uiso 1 1 calc R . . . .
C3 C 1.2154(4) 0.5876(3) 1.0468(3) 0.0285(8) Uani 1 1 d . . . . .
H3 H 1.2896 0.5766 1.1252 0.034 Uiso 1 1 calc R . . . .
C4 C 1.0925(4) 0.6461(3) 1.0380(3) 0.0266(7) Uani 1 1 d . . . . .
H4 H 1.0815 0.6743 1.1113 0.032 Uiso 1 1 calc R . . . .
C5 C 0.9848(4) 0.6646(3) 0.9252(3) 0.0250(7) Uani 1 1 d . . . . .
C6 C 0.8472(4) 0.7266(3) 0.9071(4) 0.0376(9) Uani 1 1 d . . . . .
H6A H 0.8462 0.7969 0.8585 0.056 Uiso 1 1 calc GR . . . .
H6B H 0.8443 0.7491 0.9880 0.056 Uiso 1 1 calc GR . . . .
H6C H 0.7611 0.6743 0.8632 0.056 Uiso 1 1 calc GR . . . .
C7 C 0.6055(3) 0.2833(3) 0.4139(3) 0.0237(7) Uani 1 1 d . . . . .
C8 C 0.4920(4) 0.1821(3) 0.3776(3) 0.0314(8) Uani 1 1 d . . . . .
H8A H 0.5399 0.1065 0.3884 0.038 Uiso 1 1 calc R . . . .
H8B H 0.4259 0.1878 0.2903 0.038 Uiso 1 1 calc R . . . .
C9 C 0.4067(3) 0.1928(3) 0.4646(3) 0.0264(7) Uani 1 1 d . . . . .
H9A H 0.3056 0.2168 0.4192 0.032 Uiso 1 1 calc R . . . .
H9B H 0.4008 0.1173 0.5052 0.032 Uiso 1 1 calc R . . . .
C10 C 0.4940(3) 0.2856(3) 0.5585(3) 0.0217(7) Uani 1 1 d . . . . .
I2 I 0.79401(2) 0.07659(2) 0.72369(2) 0.01872(6) Uani 1 1 d . . . . .
O4 O 0.6672(3) -0.00604(19) 0.8517(2) 0.0267(5) Uani 1 1 d . . . . .
O5 O 0.7953(2) 0.0344(2) 0.4352(2) 0.0293(5) Uani 1 1 d . . . . .
O6 O 1.0743(2) 0.2670(2) 0.7653(2) 0.0297(5) Uani 1 1 d . . . . .
N3 N 0.6178(3) 0.0718(2) 0.9123(2) 0.0228(6) Uani 1 1 d . . . . .
N4 N 0.9111(3) 0.1450(2) 0.6142(2) 0.0202(6) Uani 1 1 d . . . . .
C11 C 0.4911(4) 0.1247(3) 0.8489(3) 0.0279(8) Uani 1 1 d . . . . .
H11 H 0.4408 0.1066 0.7635 0.033 Uiso 1 1 calc R . . . .
C12 C 0.4360(4) 0.2035(3) 0.9074(3) 0.0307(8) Uani 1 1 d . . . . .
H12 H 0.3493 0.2420 0.8625 0.037 Uiso 1 1 calc R . . . .
C13 C 0.5074(4) 0.2266(3) 1.0328(3) 0.0299(8) Uani 1 1 d . . . . .
H13 H 0.4697 0.2801 1.0753 0.036 Uiso 1 1 calc R . . . .
C14 C 0.6343(4) 0.1708(3) 1.0947(3) 0.0296(8) Uani 1 1 d . . . . .
H14 H 0.6832 0.1858 1.1809 0.036 Uiso 1 1 calc R . . . .
C15 C 0.6920(3) 0.0936(3) 1.0346(3) 0.0248(7) Uani 1 1 d . . . . .
C16 C 0.8306(4) 0.0338(3) 1.0933(3) 0.0350(8) Uani 1 1 d . . . . .
H16A H 0.8102 -0.0512 1.0832 0.053 Uiso 1 1 calc GR . . . .
H16B H 0.8722 0.0548 1.1816 0.053 Uiso 1 1 calc GR . . . .
H16C H 0.9012 0.0583 1.0539 0.053 Uiso 1 1 calc GR . . . .
C17 C 1.0273(3) 0.2285(3) 0.6601(3) 0.0224(7) Uani 1 1 d . . . . .
C18 C 1.0821(4) 0.2607(3) 0.5568(3) 0.0323(8) Uani 1 1 d . . . . .
H18A H 1.1884 0.2474 0.5813 0.039 Uiso 1 1 calc R . . . .
H18B H 1.0670 0.3441 0.5355 0.039 Uiso 1 1 calc R . . . .
C19 C 0.9922(4) 0.1815(3) 0.4481(3) 0.0260(7) Uani 1 1 d . . . . .
H19A H 1.0566 0.1298 0.4242 0.031 Uiso 1 1 calc R . . . .
H19B H 0.9380 0.2284 0.3758 0.031 Uiso 1 1 calc R . . . .
C20 C 0.8859(3) 0.1100(3) 0.4930(3) 0.0220(7) Uani 1 1 d . . . . .
O7 O 0.4566(4) 0.5045(3) 0.8010(3) 0.0599(8) Uani 1 1 d . . . . .
H7A H 0.4080 0.5575 0.7554 0.090 Uiso 1 1 d G . . . .
H7B H 0.4630 0.4478 0.7559 0.090 Uiso 1 1 d G . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 O1 2.383(2) . ?
I1 N2 2.102(3) . ?
O1 N1 1.336(3) . ?
O2 C10 1.212(4) . ?
O3 C7 1.223(4) . ?
N1 C1 1.351(4) . ?
N1 C5 1.361(4) . ?
N2 C7 1.377(4) . ?
N2 C10 1.390(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.366(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.373(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.377(5) . ?
C5 C6 1.496(5) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.504(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.524(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.508(5) . ?
I2 O4 2.405(2) . ?
I2 N4 2.109(2) . ?
O4 N3 1.341(3) . ?
O5 C20 1.212(4) . ?
O6 C17 1.210(4) . ?
N3 C11 1.363(4) . ?
N3 C15 1.356(4) . ?
N4 C17 1.389(4) . ?
N4 C20 1.388(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.366(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.377(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.382(5) . ?
C15 C16 1.480(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.511(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.515(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.517(4) . ?
O7 H7A 0.8493 . ?
O7 H7B 0.8502 . ?

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
N2 I1 O1 178.12(9) . . ?
N1 O1 I1 114.92(16) . . ?
O1 N1 C1 119.4(3) . . ?
O1 N1 C5 119.1(3) . . ?
C1 N1 C5 121.5(3) . . ?
C7 N2 I1 123.5(2) . . ?
C7 N2 C10 112.2(3) . . ?
C10 N2 I1 124.3(2) . . ?
N1 C1 H1 119.7 . . ?
N1 C1 C2 120.7(3) . . ?
C2 C1 H1 119.7 . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.3(3) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.0(3) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.4(3) . . ?
C5 C4 H4 119.3 . . ?
N1 C5 C4 118.1(3) . . ?
N1 C5 C6 117.0(3) . . ?
C4 C5 C6 124.9(3) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O3 C7 N2 124.2(3) . . ?
O3 C7 C8 126.8(3) . . ?
N2 C7 C8 109.0(3) . . ?
C7 C8 H8A 110.8 . . ?
C7 C8 H8B 110.8 . . ?
C7 C8 C9 104.7(3) . . ?
H8A C8 H8B 108.9 . . ?
C9 C8 H8A 110.8 . . ?
C9 C8 H8B 110.8 . . ?
C8 C9 H9A 110.9 . . ?
C8 C9 H9B 110.9 . . ?
H9A C9 H9B 108.9 . . ?
C10 C9 C8 104.5(3) . . ?
C10 C9 H9A 110.9 . . ?
C10 C9 H9B 110.9 . . ?
O2 C10 N2 124.4(3) . . ?
O2 C10 C9 127.0(3) . . ?
N2 C10 C9 108.7(3) . . ?
N4 I2 O4 178.00(9) . . ?
N3 O4 I2 115.44(16) . . ?
O4 N3 C11 118.5(3) . . ?
O4 N3 C15 119.6(3) . . ?
C15 N3 C11 121.8(3) . . ?
C17 N4 I2 122.0(2) . . ?
C20 N4 I2 124.9(2) . . ?
C20 N4 C17 113.1(2) . . ?
N3 C11 H11 119.8 . . ?
N3 C11 C12 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.4(3) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 120.6 . . ?
C14 C13 C12 118.8(3) . . ?
C14 C13 H13 120.6 . . ?
C13 C14 H14 119.2 . . ?
C13 C14 C15 121.6(3) . . ?
C15 C14 H14 119.2 . . ?
N3 C15 C14 117.8(3) . . ?
N3 C15 C16 117.2(3) . . ?
C14 C15 C16 124.9(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O6 C17 N4 124.7(3) . . ?
O6 C17 C18 127.3(3) . . ?
N4 C17 C18 108.1(3) . . ?
C17 C18 H18A 110.6 . . ?
C17 C18 H18B 110.6 . . ?
C17 C18 C19 105.5(3) . . ?
H18A C18 H18B 108.8 . . ?
C19 C18 H18A 110.6 . . ?
C19 C18 H18B 110.6 . . ?
C18 C19 H19A 110.7 . . ?
C18 C19 H19B 110.7 . . ?
C18 C19 C20 105.2(3) . . ?
H19A C19 H19B 108.8 . . ?
C20 C19 H19A 110.7 . . ?
C20 C19 H19B 110.7 . . ?
O5 C20 N4 125.2(3) . . ?
O5 C20 C19 126.8(3) . . ?
N4 C20 C19 108.0(3) . . ?
H7A O7 H7B 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H7A O3 0.85 2.01 2.860(4) 173.6 2_666
O7 H7B O2 0.85 1.97 2.822(4) 178.7 .

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
I1 O1 N1 C1 74.4(3) . . . . ?
I1 O1 N1 C5 -106.5(3) . . . . ?
I1 N2 C7 O3 -0.9(4) . . . . ?
I1 N2 C7 C8 178.2(2) . . . . ?
I1 N2 C10 O2 -4.2(4) . . . . ?
I1 N2 C10 C9 175.26(19) . . . . ?
O1 N1 C1 C2 178.1(3) . . . . ?
O1 N1 C5 C4 -177.7(3) . . . . ?
O1 N1 C5 C6 2.3(4) . . . . ?
O3 C7 C8 C9 -172.6(3) . . . . ?
N1 C1 C2 C3 -0.5(5) . . . . ?
N2 C7 C8 C9 8.4(4) . . . . ?
C1 N1 C5 C4 1.5(4) . . . . ?
C1 N1 C5 C6 -178.5(3) . . . . ?
C1 C2 C3 C4 1.5(5) . . . . ?
C2 C3 C4 C5 -1.1(5) . . . . ?
C3 C4 C5 N1 -0.4(5) . . . . ?
C3 C4 C5 C6 179.6(3) . . . . ?
C5 N1 C1 C2 -1.0(4) . . . . ?
C7 N2 C10 O2 177.6(3) . . . . ?
C7 N2 C10 C9 -3.0(3) . . . . ?
C7 C8 C9 C10 -9.7(3) . . . . ?
C8 C9 C10 O2 -172.5(3) . . . . ?
C8 C9 C10 N2 8.0(3) . . . . ?
C10 N2 C7 O3 177.4(3) . . . . ?
C10 N2 C7 C8 -3.6(4) . . . . ?
I2 O4 N3 C11 78.9(3) . . . . ?
I2 O4 N3 C15 -102.9(2) . . . . ?
I2 N4 C17 O6 2.1(4) . . . . ?
I2 N4 C17 C18 -178.1(2) . . . . ?
I2 N4 C20 O5 -1.4(4) . . . . ?
I2 N4 C20 C19 179.39(19) . . . . ?
O4 N3 C11 C12 179.2(3) . . . . ?
O4 N3 C15 C14 -177.4(3) . . . . ?
O4 N3 C15 C16 3.5(4) . . . . ?
O6 C17 C18 C19 176.3(3) . . . . ?
N3 C11 C12 C13 -2.0(5) . . . . ?
N4 C17 C18 C19 -3.5(4) . . . . ?
C11 N3 C15 C14 0.8(4) . . . . ?
C11 N3 C15 C16 -178.3(3) . . . . ?
C11 C12 C13 C14 1.2(5) . . . . ?
C12 C13 C14 C15 0.6(5) . . . . ?
C13 C14 C15 N3 -1.6(5) . . . . ?
C13 C14 C15 C16 177.4(3) . . . . ?
C15 N3 C11 C12 1.0(4) . . . . ?
C17 N4 C20 O5 176.3(3) . . . . ?
C17 N4 C20 C19 -2.9(3) . . . . ?
C17 C18 C19 C20 1.8(3) . . . . ?
C18 C19 C20 O5 -178.7(3) . . . . ?
C18 C19 C20 N4 0.4(3) . . . . ?
C20 N4 C17 O6 -175.8(3) . . . . ?
C20 N4 C17 C18 4.1(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_3_NIS
_database_code_depnum_ccdc_archive 'CCDC 1426138'
_audit_update_record             
;
2015-09-21 deposited with the CCDC.
2015-12-15 downloaded from the CCDC.
;
_audit_creation_date             2015-08-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H13 I N2 O3'
_chemical_formula_sum            'C15 H13 I N2 O3'
_chemical_formula_weight         396.17
_chemical_absolute_configuration ?
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.7923(12)
_cell_length_b                   8.4216(17)
_cell_length_c                   29.710(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1449.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    170.0
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.221
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0787 before and 0.0623 after correction.
The Ratio of minimum to maximum transmission is 0.8141.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.816
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            24654
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.247
_diffrn_reflns_theta_max         25.247
_diffrn_reflns_theta_min         2.514
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.683
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2544
_reflns_number_total             2592
_reflns_special_details          
;
 _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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.695
_refine_diff_density_min         -1.388
_refine_diff_density_rms         0.169
_refine_ls_abs_structure_details 
;
 Flack x determined using 1011 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2592
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0383
_refine_ls_restrained_S_all      1.163
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1145P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1375
_refine_special_details          
;
 Refined as a 2-component perfect twin.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I -0.38915(9) -0.70621(6) -0.16308(2) 0.0369(3) Uani 1 1 d . . . . .
O1 O -0.6244(15) -0.5544(8) -0.2140(2) 0.0559(18) Uani 1 1 d . . . . .
O2 O 0.0787(12) -0.9326(9) -0.1668(2) 0.0526(17) Uani 1 1 d . . . . .
O3 O -0.3828(14) -0.7668(10) -0.0527(2) 0.0547(18) Uani 1 1 d . . . . .
N1 N -0.6694(14) -0.6311(8) -0.2527(2) 0.0399(16) Uani 1 1 d . . . . .
N2 N -0.1823(13) -0.8273(9) -0.1165(3) 0.0408(16) Uani 1 1 d . . . . .
C1 C -0.8599(19) -0.7215(12) -0.2555(4) 0.055(2) Uani 1 1 d . . . . .
H1 H -0.9516 -0.7390 -0.2295 0.066 Uiso 1 1 calc R . . . .
C2 C -0.9233(16) -0.7888(12) -0.2958(3) 0.045(2) Uani 1 1 d . . . . .
H2 H -1.0596 -0.8513 -0.2974 0.055 Uiso 1 1 calc R . . . .
C3 C -0.7893(15) -0.7663(9) -0.3342(3) 0.0340(17) Uani 1 1 d . . . . .
C4 C -0.5885(16) -0.6805(12) -0.3291(3) 0.0414(19) Uani 1 1 d . . . . .
H4 H -0.4877 -0.6688 -0.3541 0.050 Uiso 1 1 calc R . . . .
C5 C -0.5305(18) -0.6115(11) -0.2888(3) 0.043(2) Uani 1 1 d . . . . .
H5 H -0.3933 -0.5503 -0.2863 0.052 Uiso 1 1 calc R . . . .
C6 C -0.8616(18) -0.8323(10) -0.3787(3) 0.0373(19) Uani 1 1 d . . . . .
C7 C -1.0645(18) -0.9224(12) -0.3834(3) 0.049(2) Uani 1 1 d . . . . .
H7 H -1.1549 -0.9435 -0.3574 0.059 Uiso 1 1 calc R . . . .
C8 C -1.137(3) -0.9809(13) -0.4241(4) 0.064(3) Uani 1 1 d . . . . .
H8 H -1.2754 -1.0405 -0.4267 0.077 Uiso 1 1 calc R . . . .
C9 C -0.995(2) -0.9489(13) -0.4628(4) 0.057(3) Uani 1 1 d . . . . .
H9 H -1.0388 -0.9899 -0.4914 0.069 Uiso 1 1 calc R . . . .
C10 C -0.802(3) -0.8616(13) -0.4590(4) 0.060(3) Uani 1 1 d . . . . .
H10 H -0.7102 -0.8410 -0.4848 0.072 Uiso 1 1 calc R . . . .
C11 C -0.735(2) -0.8007(12) -0.4171(4) 0.053(3) Uani 1 1 d . . . . .
H11 H -0.6006 -0.7366 -0.4151 0.063 Uiso 1 1 calc R . . . .
C12 C 0.0156(14) -0.9097(11) -0.1286(3) 0.0376(19) Uani 1 1 d . . . . .
C13 C 0.1393(17) -0.9627(12) -0.0860(3) 0.045(2) Uani 1 1 d . . . . .
H13A H 0.2926 -0.9115 -0.0835 0.054 Uiso 1 1 calc R . . . .
H13B H 0.1596 -1.0794 -0.0856 0.054 Uiso 1 1 calc R . . . .
C14 C -0.020(2) -0.9089(13) -0.0479(3) 0.053(2) Uani 1 1 d . . . . .
H14A H -0.0771 -1.0015 -0.0307 0.063 Uiso 1 1 calc R . . . .
H14B H 0.0627 -0.8369 -0.0271 0.063 Uiso 1 1 calc R . . . .
C15 C -0.2174(17) -0.8236(11) -0.0703(3) 0.0412(19) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 O1 2.404(7) . ?
I1 N2 2.094(8) . ?
O1 N1 1.344(9) . ?
O2 C12 1.209(11) . ?
O3 C15 1.192(12) . ?
N1 C1 1.343(12) . ?
N1 C5 1.351(12) . ?
N2 C12 1.387(11) . ?
N2 C15 1.388(11) . ?
C1 H1 0.9500 . ?
C1 C2 1.373(14) . ?
C2 H2 0.9500 . ?
C2 C3 1.394(13) . ?
C3 C4 1.377(13) . ?
C3 C6 1.494(12) . ?
C4 H4 0.9500 . ?
C4 C5 1.373(12) . ?
C5 H5 0.9500 . ?
C6 C7 1.405(14) . ?
C6 C11 1.383(14) . ?
C7 H7 0.9500 . ?
C7 C8 1.373(16) . ?
C8 H8 0.9500 . ?
C8 C9 1.438(18) . ?
C9 H9 0.9500 . ?
C9 C10 1.345(17) . ?
C10 H10 0.9500 . ?
C10 C11 1.399(14) . ?
C11 H11 0.9500 . ?
C12 C13 1.520(13) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.529(14) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.506(15) . ?

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
N2 I1 O1 176.9(2) . . ?
N1 O1 I1 113.1(5) . . ?
O1 N1 C5 120.3(8) . . ?
C1 N1 O1 119.1(8) . . ?
C1 N1 C5 120.6(8) . . ?
C12 N2 I1 123.1(6) . . ?
C12 N2 C15 112.8(8) . . ?
C15 N2 I1 123.9(6) . . ?
N1 C1 H1 119.7 . . ?
N1 C1 C2 120.6(9) . . ?
C2 C1 H1 119.7 . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.5(9) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 C6 121.2(8) . . ?
C4 C3 C2 116.9(8) . . ?
C4 C3 C6 122.0(8) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 C3 121.6(8) . . ?
C5 C4 H4 119.2 . . ?
N1 C5 C4 119.7(9) . . ?
N1 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C7 C6 C3 121.6(8) . . ?
C11 C6 C3 120.7(9) . . ?
C11 C6 C7 117.7(9) . . ?
C6 C7 H7 118.8 . . ?
C8 C7 C6 122.4(10) . . ?
C8 C7 H7 118.8 . . ?
C7 C8 H8 121.2 . . ?
C7 C8 C9 117.7(12) . . ?
C9 C8 H8 121.2 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.6(10) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.4(11) . . ?
C11 C10 H10 119.8 . . ?
C6 C11 C10 121.1(11) . . ?
C6 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
O2 C12 N2 124.9(9) . . ?
O2 C12 C13 126.3(9) . . ?
N2 C12 C13 108.8(7) . . ?
C12 C13 H13A 110.9 . . ?
C12 C13 H13B 110.9 . . ?
C12 C13 C14 104.1(8) . . ?
H13A C13 H13B 108.9 . . ?
C14 C13 H13A 110.9 . . ?
C14 C13 H13B 110.9 . . ?
C13 C14 H14A 110.6 . . ?
C13 C14 H14B 110.6 . . ?
H14A C14 H14B 108.7 . . ?
C15 C14 C13 105.8(8) . . ?
C15 C14 H14A 110.6 . . ?
C15 C14 H14B 110.6 . . ?
O3 C15 N2 124.1(9) . . ?
O3 C15 C14 127.4(9) . . ?
N2 C15 C14 108.4(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 O1 N1 C1 90.9(8) . . . . ?
I1 O1 N1 C5 -92.1(8) . . . . ?
I1 N2 C12 O2 -6.8(13) . . . . ?
I1 N2 C12 C13 172.2(6) . . . . ?
I1 N2 C15 O3 9.0(14) . . . . ?
I1 N2 C15 C14 -173.7(6) . . . . ?
O1 N1 C1 C2 173.6(9) . . . . ?
O1 N1 C5 C4 -174.9(8) . . . . ?
O2 C12 C13 C14 -177.7(9) . . . . ?
N1 C1 C2 C3 0.9(15) . . . . ?
N2 C12 C13 C14 3.3(10) . . . . ?
C1 N1 C5 C4 2.1(13) . . . . ?
C1 C2 C3 C4 2.8(13) . . . . ?
C1 C2 C3 C6 -177.1(9) . . . . ?
C2 C3 C4 C5 -4.2(13) . . . . ?
C2 C3 C6 C7 -1.4(13) . . . . ?
C2 C3 C6 C11 175.9(9) . . . . ?
C3 C4 C5 N1 1.8(14) . . . . ?
C3 C6 C7 C8 178.4(9) . . . . ?
C3 C6 C11 C10 -179.8(9) . . . . ?
C4 C3 C6 C7 178.7(8) . . . . ?
C4 C3 C6 C11 -4.1(13) . . . . ?
C5 N1 C1 C2 -3.4(14) . . . . ?
C6 C3 C4 C5 175.7(8) . . . . ?
C6 C7 C8 C9 0.8(16) . . . . ?
C7 C6 C11 C10 -2.4(15) . . . . ?
C7 C8 C9 C10 -1.4(16) . . . . ?
C8 C9 C10 C11 0.2(16) . . . . ?
C9 C10 C11 C6 1.8(17) . . . . ?
C11 C6 C7 C8 1.1(15) . . . . ?
C12 N2 C15 O3 -175.8(9) . . . . ?
C12 N2 C15 C14 1.5(10) . . . . ?
C12 C13 C14 C15 -2.3(10) . . . . ?
C13 C14 C15 O3 177.8(10) . . . . ?
C13 C14 C15 N2 0.6(11) . . . . ?
C15 N2 C12 O2 177.9(9) . . . . ?
C15 N2 C12 C13 -3.1(10) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_1_NISac
_database_code_depnum_ccdc_archive 'CCDC 1426139'
_audit_update_record             
;
2015-09-21 deposited with the CCDC.
2015-12-15 downloaded from the CCDC.
;
_audit_creation_date             2015-08-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H9 I N2 O4 S'
_chemical_formula_sum            'C12 H9 I N2 O4 S'
_chemical_formula_weight         404.17
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   7.1370(14)
_cell_length_b                   22.707(5)
_cell_length_c                   8.8248(18)
_cell_angle_alpha                90
_cell_angle_beta                 90.68(3)
_cell_angle_gamma                90
_cell_volume                     1430.1(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    170
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.398
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.5339
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0839 before and 0.0636 after correction.
The Ratio of minimum to maximum transmission is 0.7159.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.877
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_av_unetI/netI     0.0753
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8791
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.246
_diffrn_reflns_theta_min         1.794
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1946
_reflns_number_total             2576
_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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.797
_refine_diff_density_min         -0.779
_refine_diff_density_rms         0.129
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2576
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0614
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0204P)²+10.8462P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1217
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.719(2) 0.281(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C4) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C5) \\sim Ueq, Uanis(C1) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.04
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C1(H1), C2(H2), C9(H9), C10(H10), C11(H11), C12(H12)
4.b Fitted hexagon refined as free rotating group:
 C3(C4,C5,N1,C1,C2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.31779(14) 0.37302(3) 0.16408(9) 0.0474(2) Uani 1 1 d . . . . .
S1 S 0.2785(4) 0.38875(11) 0.5344(3) 0.0414(7) Uani 1 1 d . . . . .
O1 O 0.3701(11) 0.3242(4) -0.0635(9) 0.057(2) Uani 1 1 d . . . . .
O2 O 0.2597(12) 0.5143(3) 0.2652(9) 0.061(2) Uani 1 1 d . . . . .
O3 O 0.4545(12) 0.3621(3) 0.5647(8) 0.052(2) Uani 1 1 d . . . . .
O4 O 0.1207(11) 0.3517(3) 0.5488(9) 0.053(2) Uani 1 1 d . . . . .
N2 N 0.2758(12) 0.4217(3) 0.3684(9) 0.041(2) Uani 1 1 d . . . . .
C3 C 0.9219(9) 0.2873(5) -0.1162(11) 0.091(5) Uani 1 1 d . . . . .
H3 H 1.0509 0.2785 -0.1288 0.109 Uiso 1 1 calc R . . . .
C4 C 0.8534(10) 0.3428(4) -0.1540(9) 0.067(3) Uani 1 1 d G U . . .
H4 H 0.9357 0.3719 -0.1926 0.080 Uiso 1 1 calc R . . . .
C5 C 0.6647(11) 0.3556(2) -0.1355(8) 0.057(3) Uani 1 1 d G U . . .
H5 H 0.6179 0.3935 -0.1614 0.068 Uiso 1 1 calc R . . . .
N1 N 0.5443(8) 0.3130(3) -0.0792(8) 0.043(2) Uani 1 1 d G . . . .
C1 C 0.6127(12) 0.2575(3) -0.0413(9) 0.072(4) Uani 1 1 d G U . . .
H1 H 0.5305 0.2284 -0.0027 0.086 Uiso 1 1 calc R . . . .
C2 C 0.8015(13) 0.2447(3) -0.0598(11) 0.099(5) Uani 1 1 d G . . . .
H2 H 0.8482 0.2068 -0.0339 0.119 Uiso 1 1 calc R . . . .
C6 C 0.2586(14) 0.4820(5) 0.3746(12) 0.042(3) Uani 1 1 d . . . . .
C7 C 0.2423(16) 0.5014(4) 0.5343(13) 0.045(3) Uani 1 1 d . . . . .
C8 C 0.2503(14) 0.4553(4) 0.6349(12) 0.039(3) Uani 1 1 d . . . . .
C9 C 0.2322(17) 0.4624(5) 0.7898(12) 0.053(3) Uani 1 1 d . . . . .
H9 H 0.2349 0.4297 0.8570 0.064 Uiso 1 1 calc R . . . .
C10 C 0.2104(18) 0.5186(5) 0.8414(16) 0.059(3) Uani 1 1 d . . . . .
H10 H 0.2063 0.5254 0.9475 0.071 Uiso 1 1 calc R . . . .
C11 C 0.194(2) 0.5664(5) 0.7423(14) 0.057(3) Uani 1 1 d . . . . .
H11 H 0.1645 0.6044 0.7802 0.068 Uiso 1 1 calc R . . . .
C12 C 0.2203(17) 0.5582(4) 0.5907(15) 0.054(3) Uani 1 1 d . . . . .
H12 H 0.2236 0.5911 0.5241 0.065 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 O1 2.328(8) . ?
I1 N2 2.139(8) . ?
S1 O3 1.417(8) . ?
S1 O4 1.413(8) . ?
S1 N2 1.646(8) . ?
S1 C8 1.765(10) . ?
O1 N1 1.278(9) . ?
O2 C6 1.213(11) . ?
N2 C6 1.375(12) . ?
C3 H3 0.9500 . ?
C3 C4 1.3900 . ?
C3 C2 1.3900 . ?
C4 H4 0.9500 . ?
C4 C5 1.3900 . ?
C5 H5 0.9500 . ?
C5 N1 1.3900 . ?
N1 C1 1.3900 . ?
C1 H1 0.9500 . ?
C1 C2 1.3900 . ?
C2 H2 0.9500 . ?
C6 C7 1.482(15) . ?
C7 C8 1.374(14) . ?
C7 C12 1.392(14) . ?
C8 C9 1.384(14) . ?
C9 H9 0.9500 . ?
C9 C10 1.365(14) . ?
C10 H10 0.9500 . ?
C10 C11 1.398(16) . ?
C11 H11 0.9500 . ?
C11 C12 1.367(16) . ?
C12 H12 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 I1 O1 177.2(3) . . ?
O3 S1 N2 111.3(5) . . ?
O3 S1 C8 112.2(5) . . ?
O4 S1 O3 115.7(5) . . ?
O4 S1 N2 110.5(5) . . ?
O4 S1 C8 111.7(5) . . ?
N2 S1 C8 93.3(4) . . ?
N1 O1 I1 110.7(5) . . ?
S1 N2 I1 121.0(4) . . ?
C6 N2 I1 124.2(6) . . ?
C6 N2 S1 114.7(7) . . ?
C4 C3 H3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.0 . . ?
N1 C5 C4 120.0 . . ?
N1 C5 H5 120.0 . . ?
O1 N1 C5 120.4(7) . . ?
O1 N1 C1 119.6(7) . . ?
C1 N1 C5 120.0 . . ?
N1 C1 H1 120.0 . . ?
C2 C1 N1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2 120.0 . . ?
O2 C6 N2 124.6(10) . . ?
O2 C6 C7 125.4(10) . . ?
N2 C6 C7 110.0(8) . . ?
C8 C7 C6 112.6(9) . . ?
C8 C7 C12 118.7(11) . . ?
C12 C7 C6 128.7(10) . . ?
C7 C8 S1 109.4(8) . . ?
C7 C8 C9 123.1(10) . . ?
C9 C8 S1 127.5(8) . . ?
C8 C9 H9 121.6 . . ?
C10 C9 C8 116.8(11) . . ?
C10 C9 H9 121.6 . . ?
C9 C10 H10 119.1 . . ?
C9 C10 C11 121.8(12) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.7(11) . . ?
C12 C11 H11 120.2 . . ?
C7 C12 H12 120.2 . . ?
C11 C12 C7 119.6(11) . . ?
C11 C12 H12 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 O1 N1 C5 -83.1(7) . . . . ?
I1 O1 N1 C1 97.7(6) . . . . ?
I1 N2 C6 O2 2.2(15) . . . . ?
I1 N2 C6 C7 -176.7(7) . . . . ?
S1 N2 C6 O2 177.6(9) . . . . ?
S1 N2 C6 C7 -1.3(11) . . . . ?
S1 C8 C9 C10 -179.5(9) . . . . ?
O1 N1 C1 C2 179.2(8) . . . . ?
O2 C6 C7 C8 -178.3(11) . . . . ?
O2 C6 C7 C12 2(2) . . . . ?
O3 S1 N2 I1 61.5(6) . . . . ?
O3 S1 N2 C6 -114.1(8) . . . . ?
O3 S1 C8 C7 113.8(8) . . . . ?
O3 S1 C8 C9 -68.2(11) . . . . ?
O4 S1 N2 I1 -68.6(6) . . . . ?
O4 S1 N2 C6 115.9(8) . . . . ?
O4 S1 C8 C7 -114.4(8) . . . . ?
O4 S1 C8 C9 63.6(11) . . . . ?
N2 S1 C8 C7 -0.8(8) . . . . ?
N2 S1 C8 C9 177.2(11) . . . . ?
N2 C6 C7 C8 0.6(13) . . . . ?
N2 C6 C7 C12 -179.1(11) . . . . ?
C3 C4 C5 N1 0.0 . . . . ?
C4 C3 C2 C1 0.0 . . . . ?
C4 C5 N1 O1 -179.1(8) . . . . ?
C4 C5 N1 C1 0.0 . . . . ?
C5 N1 C1 C2 0.0 . . . . ?
N1 C1 C2 C3 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C6 C7 C8 S1 0.2(12) . . . . ?
C6 C7 C8 C9 -177.9(11) . . . . ?
C6 C7 C12 C11 175.1(13) . . . . ?
C7 C8 C9 C10 -1.7(18) . . . . ?
C8 S1 N2 I1 176.8(6) . . . . ?
C8 S1 N2 C6 1.2(8) . . . . ?
C8 C7 C12 C11 -5(2) . . . . ?
C8 C9 C10 C11 4.3(19) . . . . ?
C9 C10 C11 C12 -7(2) . . . . ?
C10 C11 C12 C7 7(2) . . . . ?
C12 C7 C8 S1 180.0(9) . . . . ?
C12 C7 C8 C9 1.9(18) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.719(2)
2 0.281(2)

####################################################################### 
# 
# 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_2_NISac
_database_code_depnum_ccdc_archive 'CCDC 1426140'
_audit_update_record             
;
2015-09-21 deposited with the CCDC.
2015-12-15 downloaded from the CCDC.
;
_audit_creation_date             2015-08-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H11 I N2 O4 S'
_chemical_formula_sum            'C13 H11 I N2 O4 S'
_chemical_formula_weight         418.20
_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                   7.2705(15)
_cell_length_b                   8.7631(18)
_cell_length_c                   12.765(3)
_cell_angle_alpha                109.12(3)
_cell_angle_beta                 99.97(3)
_cell_angle_gamma                90.54(3)
_cell_volume                     754.9(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    170
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.275
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0687 before and 0.0511 after correction.
The Ratio of minimum to maximum transmission is 0.7845.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.840
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7107
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         25.243
_diffrn_reflns_theta_min         1.719
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2489
_reflns_number_total             2738
_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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2738
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0264
_refine_ls_restrained_S_all      1.063
_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)+(0.0184P)²+0.8524P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0593
_refine_ls_wR_factor_ref         0.0606
_refine_special_details          ?
_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.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.25647(3) 0.70967(3) 0.25876(2) 0.03745(9) Uani 1 1 d . . . . .
S1 S 0.23006(11) 0.35762(10) 0.29508(7) 0.0344(2) Uani 1 1 d . . . . .
O1 O 0.2830(3) 0.8814(3) 0.1568(2) 0.0480(7) Uani 1 1 d . . . . .
O2 O 0.2538(4) 0.7466(3) 0.5311(2) 0.0494(6) Uani 1 1 d . . . . .
O3 O 0.0577(3) 0.3021(3) 0.2170(2) 0.0477(6) Uani 1 1 d . . . . .
O4 O 0.3975(3) 0.3109(3) 0.2524(2) 0.0465(6) Uani 1 1 d . . . . .
N1 N 0.2397(4) 0.5560(3) 0.3570(3) 0.0375(7) Uani 1 1 d . . . . .
N2 N 0.4601(4) 0.8908(4) 0.1395(3) 0.0397(7) Uani 1 1 d . . . . .
C1 C 0.2450(4) 0.6064(4) 0.4714(3) 0.0348(8) Uani 1 1 d . . . . .
C2 C 0.2352(4) 0.4625(4) 0.5084(3) 0.0337(7) Uani 1 1 d . . . . .
C3 C 0.2279(4) 0.3174(4) 0.4201(3) 0.0350(8) Uani 1 1 d . . . . .
C4 C 0.2174(5) 0.1688(4) 0.4355(3) 0.0424(9) Uani 1 1 d . . . . .
H4 H 0.2124 0.0706 0.3742 0.051 Uiso 1 1 calc R . . . .
C5 C 0.2143(5) 0.1685(5) 0.5433(4) 0.0505(10) Uani 1 1 d . . . . .
H5 H 0.2081 0.0684 0.5568 0.061 Uiso 1 1 calc R . . . .
C6 C 0.2201(5) 0.3125(5) 0.6320(4) 0.0485(10) Uani 1 1 d . . . . .
H6 H 0.2164 0.3091 0.7052 0.058 Uiso 1 1 calc R . . . .
C7 C 0.2313(4) 0.4606(5) 0.6166(3) 0.0422(9) Uani 1 1 d . . . . .
H7 H 0.2361 0.5586 0.6781 0.051 Uiso 1 1 calc R . . . .
C8 C 0.5862(5) 0.9962(4) 0.2218(3) 0.0422(8) Uani 1 1 d . . . . .
H8 H 0.5491 1.0598 0.2898 0.051 Uiso 1 1 calc R . . . .
C9 C 0.7656(5) 1.0124(5) 0.2086(4) 0.0508(10) Uani 1 1 d . . . . .
H9 H 0.8541 1.0871 0.2667 0.061 Uiso 1 1 calc R . . . .
C10 C 0.8178(5) 0.9199(6) 0.1106(4) 0.0591(12) Uani 1 1 d . . . . .
H10 H 0.9429 0.9293 0.0999 0.071 Uiso 1 1 calc R . . . .
C11 C 0.6865(6) 0.8131(6) 0.0279(4) 0.0664(13) Uani 1 1 d . . . . .
H11 H 0.7219 0.7497 -0.0407 0.080 Uiso 1 1 calc R . . . .
C12 C 0.5038(5) 0.7959(5) 0.0420(3) 0.0487(9) Uani 1 1 d . . . . .
C13 C 0.3537(7) 0.6815(7) -0.0432(4) 0.0785(15) Uani 1 1 d . . . . .
H13A H 0.3052 0.6071 -0.0099 0.118 Uiso 1 1 calc GR . . . .
H13B H 0.4055 0.6196 -0.1092 0.118 Uiso 1 1 calc GR . . . .
H13C H 0.2519 0.7429 -0.0663 0.118 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
I1 O1 2.316(3) . ?
I1 N1 2.135(3) . ?
S1 O3 1.428(3) . ?
S1 O4 1.428(2) . ?
S1 N1 1.652(3) . ?
S1 C3 1.746(4) . ?
O1 N2 1.349(3) . ?
O2 C1 1.210(4) . ?
N1 C1 1.374(4) . ?
N2 C8 1.346(5) . ?
N2 C12 1.345(5) . ?
C1 C2 1.489(5) . ?
C2 C3 1.389(5) . ?
C2 C7 1.392(5) . ?
C3 C4 1.382(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(6) . ?
C6 H6 0.9500 . ?
C6 C7 1.378(5) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.356(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.368(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.374(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(5) . ?
C12 C13 1.494(6) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
N1 I1 O1 178.08(10) . . ?
O3 S1 O4 116.54(16) . . ?
O3 S1 N1 110.43(16) . . ?
O3 S1 C3 111.67(15) . . ?
O4 S1 N1 110.35(15) . . ?
O4 S1 C3 111.84(16) . . ?
N1 S1 C3 93.71(16) . . ?
N2 O1 I1 110.28(18) . . ?
S1 N1 I1 119.18(16) . . ?
C1 N1 I1 125.9(2) . . ?
C1 N1 S1 114.9(2) . . ?
C8 N2 O1 118.0(3) . . ?
C12 N2 O1 119.3(3) . . ?
C12 N2 C8 122.7(3) . . ?
O2 C1 N1 124.4(3) . . ?
O2 C1 C2 126.2(3) . . ?
N1 C1 C2 109.4(3) . . ?
C3 C2 C1 112.6(3) . . ?
C3 C2 C7 119.7(3) . . ?
C7 C2 C1 127.7(3) . . ?
C2 C3 S1 109.3(3) . . ?
C4 C3 S1 128.3(3) . . ?
C4 C3 C2 122.3(3) . . ?
C3 C4 H4 121.3 . . ?
C5 C4 C3 117.5(4) . . ?
C5 C4 H4 121.3 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.8(4) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.7(4) . . ?
C7 C6 H6 119.2 . . ?
C2 C7 H7 121.0 . . ?
C6 C7 C2 118.1(4) . . ?
C6 C7 H7 121.0 . . ?
N2 C8 H8 119.7 . . ?
N2 C8 C9 120.6(4) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 120.4 . . ?
C8 C9 C10 119.3(4) . . ?
C10 C9 H9 120.4 . . ?
C9 C10 H10 120.5 . . ?
C9 C10 C11 119.0(4) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.5(4) . . ?
C12 C11 H11 119.2 . . ?
N2 C12 C11 116.8(4) . . ?
N2 C12 C13 118.4(4) . . ?
C11 C12 C13 124.8(4) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
I1 O1 N2 C8 -83.9(3) . . . . ?
I1 O1 N2 C12 96.1(3) . . . . ?
I1 N1 C1 O2 2.6(5) . . . . ?
I1 N1 C1 C2 -178.27(19) . . . . ?
S1 N1 C1 O2 179.3(3) . . . . ?
S1 N1 C1 C2 -1.5(3) . . . . ?
S1 C3 C4 C5 -178.8(3) . . . . ?
O1 N2 C8 C9 -179.2(3) . . . . ?
O1 N2 C12 C11 178.7(3) . . . . ?
O1 N2 C12 C13 -0.8(5) . . . . ?
O2 C1 C2 C3 -179.5(3) . . . . ?
O2 C1 C2 C7 1.2(5) . . . . ?
O3 S1 N1 I1 -67.3(2) . . . . ?
O3 S1 N1 C1 115.8(2) . . . . ?
O3 S1 C3 C2 -113.8(2) . . . . ?
O3 S1 C3 C4 65.0(3) . . . . ?
O4 S1 N1 I1 63.0(2) . . . . ?
O4 S1 N1 C1 -113.9(2) . . . . ?
O4 S1 C3 C2 113.6(2) . . . . ?
O4 S1 C3 C4 -67.6(3) . . . . ?
N1 S1 C3 C2 -0.1(2) . . . . ?
N1 S1 C3 C4 178.8(3) . . . . ?
N1 C1 C2 C3 1.4(4) . . . . ?
N1 C1 C2 C7 -178.0(3) . . . . ?
N2 C8 C9 C10 -0.2(6) . . . . ?
C1 C2 C3 S1 -0.7(3) . . . . ?
C1 C2 C3 C4 -179.7(3) . . . . ?
C1 C2 C7 C6 179.4(3) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C3 S1 N1 I1 177.98(16) . . . . ?
C3 S1 N1 C1 1.0(2) . . . . ?
C3 C2 C7 C6 0.0(4) . . . . ?
C3 C4 C5 C6 0.5(5) . . . . ?
C4 C5 C6 C7 -0.7(5) . . . . ?
C5 C6 C7 C2 0.4(5) . . . . ?
C7 C2 C3 S1 178.7(2) . . . . ?
C7 C2 C3 C4 -0.2(5) . . . . ?
C8 N2 C12 C11 -1.3(6) . . . . ?
C8 N2 C12 C13 179.2(4) . . . . ?
C8 C9 C10 C11 0.2(6) . . . . ?
C9 C10 C11 C12 -0.8(7) . . . . ?
C10 C11 C12 N2 1.3(7) . . . . ?
C10 C11 C12 C13 -179.3(5) . . . . ?
C12 N2 C8 C9 0.8(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_3_NISac
_database_code_depnum_ccdc_archive 'CCDC 1426141'
_audit_update_record             
;
2015-09-21 deposited with the CCDC.
2015-12-15 downloaded from the CCDC.
;
_audit_creation_date             2015-08-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H13 I N2 O4 S'
_chemical_formula_sum            'C18 H13 I N2 O4 S'
_chemical_formula_weight         480.26
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.277(3)
_cell_length_b                   10.283(2)
_cell_length_c                   14.972(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.71(3)
_cell_angle_gamma                90
_cell_volume                     1810.3(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    170
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.910
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0784 before and 0.0636 after correction.
The Ratio of minimum to maximum transmission is 0.7805.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16159
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.248
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_min         1.732
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2144
_reflns_number_total             3276
_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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0151P)²+2.1819P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0637
_refine_ls_wR_factor_ref         0.0734
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11),
 C15(H15), C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.18396(3) 0.12157(3) 0.15788(2) 0.05913(13) Uani 1 1 d . . . . .
S1 S 0.40300(12) -0.07289(13) 0.19487(8) 0.0624(4) Uani 1 1 d . . . . .
O1 O 0.0816(3) 0.2820(3) 0.2068(2) 0.0680(10) Uani 1 1 d . . . . .
O2 O 0.2064(3) -0.0158(3) -0.0417(2) 0.0724(10) Uani 1 1 d . . . . .
O3 O 0.4662(3) 0.0346(4) 0.2430(2) 0.0791(11) Uani 1 1 d . . . . .
O4 O 0.3750(4) -0.1723(4) 0.2503(2) 0.0876(12) Uani 1 1 d . . . . .
N1 N 0.0200(3) 0.2389(4) 0.2622(3) 0.0573(11) Uani 1 1 d . . . . .
N2 N 0.2870(3) -0.0210(4) 0.1165(2) 0.0570(11) Uani 1 1 d . . . . .
C1 C -0.0648(4) 0.1519(5) 0.2303(4) 0.0628(14) Uani 1 1 d . . . . .
H1 H -0.0805 0.1198 0.1684 0.075 Uiso 1 1 calc R . . . .
C2 C -0.1273(4) 0.1103(5) 0.2854(3) 0.0611(13) Uani 1 1 d . . . . .
H2 H -0.1869 0.0496 0.2614 0.073 Uiso 1 1 calc R . . . .
C3 C -0.1063(4) 0.1546(5) 0.3775(3) 0.0556(13) Uani 1 1 d . . . . .
C4 C -0.0202(5) 0.2459(5) 0.4060(4) 0.0672(15) Uani 1 1 d . . . . .
H4 H -0.0049 0.2822 0.4667 0.081 Uiso 1 1 calc R . . . .
C5 C 0.0432(5) 0.2851(5) 0.3494(4) 0.0670(15) Uani 1 1 d . . . . .
H5 H 0.1038 0.3450 0.3719 0.080 Uiso 1 1 calc R . . . .
C6 C -0.1733(4) 0.1110(5) 0.4389(3) 0.0582(13) Uani 1 1 d . . . . .
C7 C -0.2869(5) 0.0766(5) 0.4044(4) 0.0629(14) Uani 1 1 d . . . . .
H7 H -0.3222 0.0789 0.3390 0.075 Uiso 1 1 calc R . . . .
C8 C -0.3488(5) 0.0395(5) 0.4626(4) 0.0707(15) Uani 1 1 d . . . . .
H8 H -0.4265 0.0162 0.4375 0.085 Uiso 1 1 calc R . . . .
C9 C -0.2994(5) 0.0357(5) 0.5573(4) 0.0752(16) Uani 1 1 d . . . . .
H9 H -0.3430 0.0121 0.5979 0.090 Uiso 1 1 calc R . . . .
C10 C -0.1860(6) 0.0663(6) 0.5927(4) 0.0809(17) Uani 1 1 d . . . . .
H10 H -0.1508 0.0607 0.6580 0.097 Uiso 1 1 calc R . . . .
C11 C -0.1229(5) 0.1048(5) 0.5351(4) 0.0739(16) Uani 1 1 d . . . . .
H11 H -0.0451 0.1273 0.5607 0.089 Uiso 1 1 calc R . . . .
C12 C 0.2843(4) -0.0486(5) 0.0257(3) 0.0560(13) Uani 1 1 d . . . . .
C13 C 0.3885(4) -0.1167(4) 0.0227(3) 0.0521(12) Uani 1 1 d . . . . .
C14 C 0.4634(4) -0.1354(5) 0.1112(3) 0.0549(12) Uani 1 1 d . . . . .
C15 C 0.5691(5) -0.1904(5) 0.1246(4) 0.0702(15) Uani 1 1 d . . . . .
H15 H 0.6191 -0.2030 0.1855 0.084 Uiso 1 1 calc R . . . .
C16 C 0.6000(5) -0.2267(5) 0.0459(4) 0.0722(15) Uani 1 1 d . . . . .
H16 H 0.6730 -0.2632 0.0526 0.087 Uiso 1 1 calc R . . . .
C17 C 0.5250(5) -0.2102(5) -0.0423(4) 0.0709(15) Uani 1 1 d . . . . .
H17 H 0.5471 -0.2370 -0.0953 0.085 Uiso 1 1 calc R . . . .
C18 C 0.4203(5) -0.1562(5) -0.0547(3) 0.0629(14) Uani 1 1 d . . . . .
H18 H 0.3697 -0.1459 -0.1156 0.076 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 O1 2.317(3) . ?
I1 N2 2.141(4) . ?
S1 O3 1.421(4) . ?
S1 O4 1.420(4) . ?
S1 N2 1.652(4) . ?
S1 C14 1.752(5) . ?
O1 N1 1.348(5) . ?
O2 C12 1.221(5) . ?
N1 C1 1.352(6) . ?
N1 C5 1.340(6) . ?
N2 C12 1.380(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.348(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.404(6) . ?
C3 C4 1.385(7) . ?
C3 C6 1.470(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.366(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(7) . ?
C6 C11 1.396(7) . ?
C7 H7 0.9500 . ?
C7 C8 1.366(7) . ?
C8 H8 0.9500 . ?
C8 C9 1.373(7) . ?
C9 H9 0.9500 . ?
C9 C10 1.376(8) . ?
C10 H10 0.9500 . ?
C10 C11 1.373(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.471(7) . ?
C13 C14 1.392(6) . ?
C13 C18 1.385(6) . ?
C14 C15 1.376(7) . ?
C15 H15 0.9500 . ?
C15 C16 1.390(7) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(7) . ?
C17 H17 0.9500 . ?
C17 C18 1.363(7) . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 I1 O1 176.86(13) . . ?
O3 S1 N2 110.0(2) . . ?
O3 S1 C14 111.5(2) . . ?
O4 S1 O3 116.9(2) . . ?
O4 S1 N2 110.1(2) . . ?
O4 S1 C14 112.2(2) . . ?
N2 S1 C14 93.8(2) . . ?
N1 O1 I1 114.3(3) . . ?
O1 N1 C1 120.7(4) . . ?
C5 N1 O1 118.9(4) . . ?
C5 N1 C1 120.3(5) . . ?
S1 N2 I1 118.42(19) . . ?
C12 N2 I1 125.3(3) . . ?
C12 N2 S1 113.9(3) . . ?
N1 C1 H1 119.7 . . ?
C2 C1 N1 120.6(5) . . ?
C2 C1 H1 119.7 . . ?
C1 C2 H2 119.3 . . ?
C1 C2 C3 121.4(5) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 C6 122.5(4) . . ?
C4 C3 C2 115.5(5) . . ?
C4 C3 C6 121.9(4) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 C3 121.9(5) . . ?
C5 C4 H4 119.0 . . ?
N1 C5 C4 120.0(5) . . ?
N1 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C7 C6 C3 121.9(4) . . ?
C7 C6 C11 118.2(5) . . ?
C11 C6 C3 119.8(5) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.2(5) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.3(5) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.4 . . ?
C8 C9 C10 119.3(5) . . ?
C10 C9 H9 120.4 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.0(5) . . ?
C11 C10 H10 119.5 . . ?
C6 C11 H11 120.0 . . ?
C10 C11 C6 119.9(5) . . ?
C10 C11 H11 120.0 . . ?
O2 C12 N2 123.2(5) . . ?
O2 C12 C13 126.0(4) . . ?
N2 C12 C13 110.7(4) . . ?
C14 C13 C12 112.3(4) . . ?
C18 C13 C12 128.5(4) . . ?
C18 C13 C14 119.2(5) . . ?
C13 C14 S1 109.3(4) . . ?
C15 C14 S1 128.4(4) . . ?
C15 C14 C13 122.2(5) . . ?
C14 C15 H15 121.2 . . ?
C14 C15 C16 117.5(5) . . ?
C16 C15 H15 121.2 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.5(5) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.3 . . ?
C18 C17 C16 121.4(5) . . ?
C18 C17 H17 119.3 . . ?
C13 C18 H18 120.4 . . ?
C17 C18 C13 119.2(5) . . ?
C17 C18 H18 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 O1 N1 C1 -62.5(5) . . . . ?
I1 O1 N1 C5 118.3(4) . . . . ?
I1 N2 C12 O2 -16.8(7) . . . . ?
I1 N2 C12 C13 161.0(3) . . . . ?
S1 N2 C12 O2 -178.6(4) . . . . ?
S1 N2 C12 C13 -0.8(5) . . . . ?
S1 C14 C15 C16 -176.6(4) . . . . ?
O1 N1 C1 C2 -179.1(4) . . . . ?
O1 N1 C5 C4 178.1(4) . . . . ?
O2 C12 C13 C14 177.3(5) . . . . ?
O2 C12 C13 C18 0.6(8) . . . . ?
O3 S1 N2 I1 -47.3(3) . . . . ?
O3 S1 N2 C12 115.9(4) . . . . ?
O3 S1 C14 C13 -114.8(4) . . . . ?
O3 S1 C14 C15 62.5(5) . . . . ?
O4 S1 N2 I1 82.9(3) . . . . ?
O4 S1 N2 C12 -113.9(4) . . . . ?
O4 S1 C14 C13 111.9(4) . . . . ?
O4 S1 C14 C15 -70.7(5) . . . . ?
N1 C1 C2 C3 -0.5(8) . . . . ?
N2 S1 C14 C13 -1.6(4) . . . . ?
N2 S1 C14 C15 175.8(5) . . . . ?
N2 C12 C13 C14 -0.4(6) . . . . ?
N2 C12 C13 C18 -177.2(5) . . . . ?
C1 N1 C5 C4 -1.1(7) . . . . ?
C1 C2 C3 C4 1.9(7) . . . . ?
C1 C2 C3 C6 179.9(5) . . . . ?
C2 C3 C4 C5 -3.0(8) . . . . ?
C2 C3 C6 C7 -30.8(7) . . . . ?
C2 C3 C6 C11 149.9(5) . . . . ?
C3 C4 C5 N1 2.7(8) . . . . ?
C3 C6 C7 C8 -178.3(5) . . . . ?
C3 C6 C11 C10 178.8(5) . . . . ?
C4 C3 C6 C7 147.0(5) . . . . ?
C4 C3 C6 C11 -32.2(7) . . . . ?
C5 N1 C1 C2 0.1(7) . . . . ?
C6 C3 C4 C5 179.0(5) . . . . ?
C6 C7 C8 C9 0.1(8) . . . . ?
C7 C6 C11 C10 -0.4(8) . . . . ?
C7 C8 C9 C10 -1.7(8) . . . . ?
C8 C9 C10 C11 2.3(9) . . . . ?
C9 C10 C11 C6 -1.2(9) . . . . ?
C11 C6 C7 C8 1.0(8) . . . . ?
C12 C13 C14 S1 1.4(5) . . . . ?
C12 C13 C14 C15 -176.2(5) . . . . ?
C12 C13 C18 C17 175.3(5) . . . . ?
C13 C14 C15 C16 0.4(8) . . . . ?
C14 S1 N2 I1 -161.8(2) . . . . ?
C14 S1 N2 C12 1.4(4) . . . . ?
C14 C13 C18 C17 -1.3(7) . . . . ?
C14 C15 C16 C17 -1.4(8) . . . . ?
C15 C16 C17 C18 1.1(8) . . . . ?
C16 C17 C18 C13 0.3(8) . . . . ?
C18 C13 C14 S1 178.5(4) . . . . ?
C18 C13 C14 C15 0.9(8) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_1_NSacH
_database_code_depnum_ccdc_archive 'CCDC 1426142'
_audit_update_record             
;
2015-09-21 deposited with the CCDC.
2015-12-15 downloaded from the CCDC.
;
_audit_creation_date             2015-09-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H5 N O3 S, C5 H5 N O'
_chemical_formula_sum            'C12 H10 N2 O4 S'
_chemical_formula_weight         278.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H10 N2 S1 O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   6.8571(4)
_cell_length_b                   8.4482(5)
_cell_length_c                   11.3117(6)
_cell_angle_alpha                98.755(5)
_cell_angle_beta                 106.766(5)
_cell_angle_gamma                93.582(5)
_cell_volume                     616.19(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2588
_cell_measurement_temperature    123
_cell_measurement_theta_max      28.6700
_cell_measurement_theta_min      3.8180
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88977
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.2357
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.0497
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4086
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.246
_diffrn_reflns_theta_min         3.122
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0053
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -87.00   12.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.1368  -77.0000   30.0000 99

#__ type_ start__ end____ width___ exp.time_
  2 omega  -86.00    7.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.1368  -19.0000 -150.0000 93

#__ type_ start__ end____ width___ exp.time_
  3 omega  -44.00   46.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.1368   77.0000  150.0000 90

#__ type_ start__ end____ width___ exp.time_
  4 omega  -93.00  -40.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.1368 -178.0000  120.0000 53

#__ type_ start__ end____ width___ exp.time_
  5 omega   24.00   61.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       19.3868  -99.0000  -60.0000 37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0291600000
_diffrn_orient_matrix_UB_12      0.0829525000
_diffrn_orient_matrix_UB_13      0.0258948000
_diffrn_orient_matrix_UB_21      -0.0958153000
_diffrn_orient_matrix_UB_22      0.0055450000
_diffrn_orient_matrix_UB_23      0.0116434000
_diffrn_orient_matrix_UB_31      0.0423024000
_diffrn_orient_matrix_UB_32      -0.0199203000
_diffrn_orient_matrix_UB_33      0.0601937000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1968
_reflns_number_total             2224
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2224
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0374
_refine_ls_restrained_S_all      1.162
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0434P)²+0.3115P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1015
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N2-H2
 1 with sigma of 0.001
3.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C1(H1), C2(H2A), C3(H3), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.38030(7) 0.49120(6) 0.26281(5) 0.01801(17) Uani 1 1 d . . . . .
O2 O 0.2472(2) 0.15618(17) -0.01102(13) 0.0210(3) Uani 1 1 d . . . . .
O3 O 0.5919(2) 0.5361(2) 0.33182(14) 0.0276(4) Uani 1 1 d . . . . .
O4 O 0.2353(2) 0.51862(19) 0.33139(14) 0.0253(4) Uani 1 1 d . . . . .
N2 N 0.3440(3) 0.3032(2) 0.18868(16) 0.0180(4) Uani 1 1 d D . . . .
H2 H 0.385(5) 0.213(2) 0.235(2) 0.067(10) Uiso 1 1 d D . . . .
C6 C 0.2797(3) 0.2845(2) 0.05945(18) 0.0149(4) Uani 1 1 d . . . . .
C7 C 0.2586(3) 0.4450(2) 0.02169(18) 0.0148(4) Uani 1 1 d . . . . .
C8 C 0.3111(3) 0.5700(2) 0.12368(19) 0.0168(4) Uani 1 1 d . . . . .
C9 C 0.3040(3) 0.7300(3) 0.1113(2) 0.0213(5) Uani 1 1 d . . . . .
H9 H 0.3395 0.8141 0.1824 0.026 Uiso 1 1 calc R . . . .
C10 C 0.2421(3) 0.7619(3) -0.0104(2) 0.0231(5) Uani 1 1 d . . . . .
H10 H 0.2358 0.8703 -0.0230 0.028 Uiso 1 1 calc R . . . .
C11 C 0.1896(3) 0.6381(3) -0.1135(2) 0.0215(5) Uani 1 1 d . . . . .
H11 H 0.1480 0.6632 -0.1955 0.026 Uiso 1 1 calc R . . . .
C12 C 0.1966(3) 0.4779(3) -0.09905(19) 0.0174(4) Uani 1 1 d . . . . .
H12 H 0.1601 0.3934 -0.1699 0.021 Uiso 1 1 calc R . . . .
O1 O 0.4803(2) 0.07461(17) 0.31081(13) 0.0201(3) Uani 1 1 d . . . . .
N1 N 0.6847(2) 0.1054(2) 0.34812(15) 0.0153(4) Uani 1 1 d . . . . .
C1 C 0.7774(3) 0.2221(3) 0.44706(19) 0.0204(5) Uani 1 1 d . . . . .
H1 H 0.6974 0.2812 0.4902 0.025 Uiso 1 1 calc R . . . .
C2 C 0.9867(3) 0.2566(3) 0.4863(2) 0.0248(5) Uani 1 1 d . . . . .
H2A H 1.0512 0.3401 0.5558 0.030 Uiso 1 1 calc R . . . .
C3 C 1.1032(3) 0.1696(3) 0.4246(2) 0.0281(5) Uani 1 1 d . . . . .
H3 H 1.2485 0.1909 0.4517 0.034 Uiso 1 1 calc R . . . .
C4 C 1.0045(3) 0.0508(3) 0.3224(2) 0.0280(5) Uani 1 1 d . . . . .
H4 H 1.0820 -0.0095 0.2782 0.034 Uiso 1 1 calc R . . . .
C5 C 0.7942(3) 0.0198(3) 0.2847(2) 0.0208(5) Uani 1 1 d . . . . .
H5 H 0.7264 -0.0615 0.2143 0.025 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4305(15) . ?
S1 O4 1.4361(15) . ?
S1 N2 1.6466(18) . ?
S1 C8 1.753(2) . ?
O2 C6 1.210(2) . ?
N2 H2 1.0000(10) . ?
N2 C6 1.380(3) . ?
C6 C7 1.486(3) . ?
C7 C8 1.385(3) . ?
C7 C12 1.385(3) . ?
C8 C9 1.382(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.392(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.390(3) . ?
C12 H12 0.9500 . ?
O1 N1 1.338(2) . ?
N1 C1 1.343(3) . ?
N1 C5 1.350(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.372(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.381(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.376(3) . ?
C5 H5 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O4 116.59(9) . . ?
O3 S1 N2 110.48(9) . . ?
O3 S1 C8 111.92(9) . . ?
O4 S1 N2 110.64(9) . . ?
O4 S1 C8 111.32(9) . . ?
N2 S1 C8 93.56(9) . . ?
S1 N2 H2 120.9(16) . . ?
C6 N2 S1 114.87(14) . . ?
C6 N2 H2 123.7(17) . . ?
O2 C6 N2 124.57(18) . . ?
O2 C6 C7 125.91(18) . . ?
N2 C6 C7 109.52(17) . . ?
C8 C7 C6 112.56(18) . . ?
C8 C7 C12 120.00(19) . . ?
C12 C7 C6 127.44(18) . . ?
C7 C8 S1 109.48(15) . . ?
C9 C8 S1 127.69(17) . . ?
C9 C8 C7 122.8(2) . . ?
C8 C9 H9 121.6 . . ?
C8 C9 C10 116.7(2) . . ?
C10 C9 H9 121.6 . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.13(19) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.2(2) . . ?
C12 C11 H11 119.4 . . ?
C7 C12 C11 118.08(19) . . ?
C7 C12 H12 121.0 . . ?
C11 C12 H12 121.0 . . ?
O1 N1 C1 119.50(16) . . ?
O1 N1 C5 119.42(17) . . ?
C1 N1 C5 121.07(18) . . ?
N1 C1 H1 119.7 . . ?
N1 C1 C2 120.5(2) . . ?
C2 C1 H1 119.7 . . ?
C1 C2 H2A 120.1 . . ?
C1 C2 C3 119.8(2) . . ?
C3 C2 H2A 120.1 . . ?
C2 C3 H3 120.7 . . ?
C2 C3 C4 118.7(2) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
N1 C5 C4 119.8(2) . . ?
N1 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-9 3 3 0.1126 -9.0000 3.0000 3.0000 0.0641 0.9139 -0.2599
10 -3 -3 0.1070 10.0000 -3.0000 -3.0000 -0.0349 -1.0097 0.3022
1 12 -2 0.0295 1.0000 12.0000 -2.0000 0.9728 -0.0526 -0.3171
0 -12 6 0.0400 -0.0000 -12.0000 6.0000 -0.8401 0.0033 0.6002
2 -4 14 0.0558 2.0000 -4.0000 14.0000 0.0890 -0.0508 1.0070
0 10 -10 0.0410 0.0000 10.0000 -10.0000 0.5706 -0.0610 -0.8011
-1 -11 -3 0.0541 -1.0000 -11.0000 -3.0000 -1.0193 -0.0001 -0.0038
2 7 10 0.0523 2.0000 7.0000 10.0000 0.8979 -0.0364 0.5471
6 -7 -9 0.0663 6.0000 -7.0000 -9.0000 -0.6388 -0.7185 -0.1485
0 3 -15 0.0473 0.0000 3.0000 -15.0000 -0.1396 -0.1580 -0.9627
-6 9 2 0.0612 -6.0000 9.0000 2.0000 0.6234 0.6481 -0.3127
-1 -1 16 0.0418 -1.0000 -1.0000 16.0000 0.3022 0.2766 0.9407
1 -12 1 0.0295 1.0000 -12.0000 1.0000 -0.9404 -0.1507 0.3415
-1 12 0 0.0171 -1.0000 12.0000 -0.0000 0.9663 0.1624 -0.2813
-7 -7 1 0.1037 -7.0000 -7.0000 1.0000 -0.7589 0.6435 -0.0965

_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_2_NSacH
_database_code_depnum_ccdc_archive 'CCDC 1426143'
_audit_update_record             
;
2015-09-21 deposited with the CCDC.
2015-12-15 downloaded from the CCDC.
;
_audit_creation_date             2015-09-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H5 N O3 S, C6 H7 N O'
_chemical_formula_sum            'C13 H12 N2 O4 S'
_chemical_formula_weight         292.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C26 H16 S1 N1 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   14.1204(10)
_cell_length_b                   6.8482(4)
_cell_length_c                   14.7897(13)
_cell_angle_alpha                90
_cell_angle_beta                 112.860(10)
_cell_angle_gamma                90
_cell_volume                     1317.83(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1225
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.2830
_cell_measurement_theta_min      3.8660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38342
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.3164
_exptl_crystal_size_mid          0.0472
_exptl_crystal_size_min          0.0361
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4484
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_min         3.329
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0053
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -92.00    7.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.9470  -77.0000  -90.0000 99

#__ type_ start__ end____ width___ exp.time_
  2 omega  -92.00   19.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.9470  -19.0000  -90.0000 111
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0068655000
_diffrn_orient_matrix_UB_12      0.0362410000
_diffrn_orient_matrix_UB_13      0.0420087000
_diffrn_orient_matrix_UB_21      0.0533697000
_diffrn_orient_matrix_UB_22      -0.0108611000
_diffrn_orient_matrix_UB_23      0.0281460000
_diffrn_orient_matrix_UB_31      0.0086605000
_diffrn_orient_matrix_UB_32      0.0963481000
_diffrn_orient_matrix_UB_33      -0.0125695000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1695
_reflns_number_total             2377
_reflns_odcompleteness_completeness 99.12
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.656
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2377
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0527
_refine_ls_restrained_S_all      1.067
_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)+(0.0620P)²+0.1591P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1302
_refine_ls_wR_factor_ref         0.1483
_refine_special_details          ?
_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. Restrained distances
 N2-H2
 1 with sigma of 0.001
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
3.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.71818(6) 0.24775(11) 0.65268(5) 0.0192(3) Uani 1 1 d . . . . .
O2 O 0.75786(16) 0.0655(3) 0.69985(15) 0.0275(6) Uani 1 1 d . . . . .
O3 O 0.75697(16) 0.4206(3) 0.70973(16) 0.0294(6) Uani 1 1 d . . . . .
O4 O 0.63670(18) 0.2789(3) 0.38191(16) 0.0287(6) Uani 1 1 d . . . . .
N2 N 0.73198(19) 0.2627(3) 0.54776(19) 0.0200(6) Uani 1 1 d D . . . .
H2 H 0.8037(11) 0.290(6) 0.553(3) 0.083(15) Uiso 1 1 d D . . . .
C1 C 0.6411(2) 0.2660(4) 0.4654(2) 0.0203(7) Uani 1 1 d . . . . .
C2 C 0.5522(2) 0.2531(4) 0.4957(2) 0.0171(7) Uani 1 1 d . . . . .
C3 C 0.5833(2) 0.2453(4) 0.5970(2) 0.0175(7) Uani 1 1 d . . . . .
C4 C 0.5154(2) 0.2354(4) 0.6439(3) 0.0246(8) Uani 1 1 d . . . . .
H4 H 0.5382 0.2296 0.7133 0.030 Uiso 1 1 calc R . . . .
C5 C 0.4111(3) 0.2345(4) 0.5823(3) 0.0283(8) Uani 1 1 d . . . . .
H5 H 0.3613 0.2283 0.6107 0.034 Uiso 1 1 calc R . . . .
C6 C 0.3781(3) 0.2425(4) 0.4808(3) 0.0270(8) Uani 1 1 d . . . . .
H6 H 0.3066 0.2412 0.4412 0.032 Uiso 1 1 calc R . . . .
C7 C 0.4486(2) 0.2524(4) 0.4364(2) 0.0228(7) Uani 1 1 d . . . . .
H7 H 0.4261 0.2586 0.3670 0.027 Uiso 1 1 calc R . . . .
O1 O 0.90806(15) 0.3661(3) 0.55154(15) 0.0201(5) Uani 1 1 d . . . . .
N1 N 0.89258(17) 0.5480(3) 0.51526(18) 0.0165(6) Uani 1 1 d . . . . .
C8 C 0.8467(2) 0.5713(4) 0.4167(2) 0.0194(7) Uani 1 1 d . . . . .
H8 H 0.8263 0.4596 0.3755 0.023 Uiso 1 1 calc R . . . .
C9 C 0.8295(2) 0.7529(4) 0.3760(2) 0.0222(7) Uani 1 1 d . . . . .
H9 H 0.7978 0.7679 0.3068 0.027 Uiso 1 1 calc R . . . .
C10 C 0.8584(2) 0.9149(4) 0.4360(2) 0.0235(7) Uani 1 1 d . . . . .
H10 H 0.8464 1.0426 0.4088 0.028 Uiso 1 1 calc R . . . .
C11 C 0.9049(2) 0.8886(5) 0.5364(2) 0.0236(7) Uani 1 1 d . . . . .
H11 H 0.9252 0.9995 0.5781 0.028 Uiso 1 1 calc R . . . .
C12 C 0.9224(2) 0.7038(4) 0.5771(2) 0.0192(7) Uani 1 1 d . . . . .
C13 C 0.9706(2) 0.6605(5) 0.6841(2) 0.0260(8) Uani 1 1 d . . . . .
H13A H 0.9212 0.5914 0.7042 0.039 Uiso 1 1 calc GR . . . .
H13B H 0.9909 0.7829 0.7209 0.039 Uiso 1 1 calc GR . . . .
H13C H 1.0315 0.5785 0.6976 0.039 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.433(2) . ?
S1 O3 1.433(2) . ?
S1 N2 1.641(3) . ?
S1 C3 1.757(3) . ?
O4 C1 1.215(4) . ?
N2 H2 1.0000(11) . ?
N2 C1 1.384(4) . ?
C1 C2 1.492(4) . ?
C2 C3 1.388(4) . ?
C2 C7 1.383(4) . ?
C3 C4 1.386(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.399(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.390(5) . ?
C7 H7 0.9500 . ?
O1 N1 1.340(3) . ?
N1 C8 1.355(4) . ?
N1 C12 1.362(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.362(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.380(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.381(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(4) . ?
C12 C13 1.490(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
O2 S1 O3 116.41(14) . . ?
O2 S1 N2 110.32(13) . . ?
O2 S1 C3 111.56(13) . . ?
O3 S1 N2 110.27(13) . . ?
O3 S1 C3 112.36(13) . . ?
N2 S1 C3 93.61(14) . . ?
S1 N2 H2 115(2) . . ?
C1 N2 S1 115.0(2) . . ?
C1 N2 H2 129(2) . . ?
O4 C1 N2 124.0(3) . . ?
O4 C1 C2 126.4(3) . . ?
N2 C1 C2 109.6(3) . . ?
C3 C2 C1 112.1(3) . . ?
C7 C2 C1 128.0(3) . . ?
C7 C2 C3 119.8(3) . . ?
C2 C3 S1 109.6(2) . . ?
C4 C3 S1 126.9(3) . . ?
C4 C3 C2 123.5(3) . . ?
C3 C4 H4 122.2 . . ?
C3 C4 C5 115.6(3) . . ?
C5 C4 H4 122.2 . . ?
C4 C5 H5 119.0 . . ?
C6 C5 C4 122.0(3) . . ?
C6 C5 H5 119.0 . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.7(3) . . ?
C7 C6 H6 119.7 . . ?
C2 C7 C6 118.4(3) . . ?
C2 C7 H7 120.8 . . ?
C6 C7 H7 120.8 . . ?
O1 N1 C8 118.4(2) . . ?
O1 N1 C12 120.0(2) . . ?
C8 N1 C12 121.6(3) . . ?
N1 C8 H8 119.6 . . ?
N1 C8 C9 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.5(3) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 120.5 . . ?
C9 C10 C11 119.0(3) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
N1 C12 C11 117.9(3) . . ?
N1 C12 C13 116.9(3) . . ?
C11 C12 C13 125.2(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
S1 N2 C1 O4 179.1(2) . . . . ?
S1 N2 C1 C2 -0.4(3) . . . . ?
S1 C3 C4 C5 -179.6(2) . . . . ?
O2 S1 N2 C1 114.2(2) . . . . ?
O2 S1 C3 C2 -112.5(2) . . . . ?
O2 S1 C3 C4 67.0(3) . . . . ?
O3 S1 N2 C1 -115.8(2) . . . . ?
O3 S1 C3 C2 114.7(2) . . . . ?
O3 S1 C3 C4 -65.9(3) . . . . ?
O4 C1 C2 C3 -178.3(3) . . . . ?
O4 C1 C2 C7 0.3(5) . . . . ?
N2 S1 C3 C2 1.0(2) . . . . ?
N2 S1 C3 C4 -179.5(3) . . . . ?
N2 C1 C2 C3 1.2(3) . . . . ?
N2 C1 C2 C7 179.8(3) . . . . ?
C1 C2 C3 S1 -1.4(3) . . . . ?
C1 C2 C3 C4 179.1(3) . . . . ?
C1 C2 C7 C6 -178.9(3) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 S1 N2 C1 -0.3(2) . . . . ?
C3 C2 C7 C6 -0.4(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C7 -0.2(5) . . . . ?
C5 C6 C7 C2 0.3(4) . . . . ?
C7 C2 C3 S1 179.9(2) . . . . ?
C7 C2 C3 C4 0.4(4) . . . . ?
O1 N1 C8 C9 -179.8(2) . . . . ?
O1 N1 C12 C11 180.0(2) . . . . ?
O1 N1 C12 C13 -0.7(4) . . . . ?
N1 C8 C9 C10 -0.6(4) . . . . ?
C8 N1 C12 C11 -0.2(4) . . . . ?
C8 N1 C12 C13 179.1(3) . . . . ?
C8 C9 C10 C11 0.5(4) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C10 C11 C12 N1 0.1(4) . . . . ?
C10 C11 C12 C13 -179.1(3) . . . . ?
C12 N1 C8 C9 0.4(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-16 0 -6 0.0214 -16.0000 -0.0000 -6.0000 -0.1422 -1.0228 -0.0632
15 -1 6 0.0098 15.0000 -1.0000 6.0000 0.1128 0.9803 -0.0419
5 9 -7 0.1377 5.0000 9.0000 -7.0000 -0.0022 -0.0279 0.9984
-6 -9 6 0.1412 -6.0000 -9.0000 6.0000 -0.0329 -0.0536 -0.9945
-13 0 20 0.0192 -13.0000 -0.0000 20.0000 0.9294 -0.1309 -0.3640
13 0 -20 0.0280 13.0000 0.0000 -20.0000 -0.9294 0.1309 0.3640
-20 1 7 0.0216 -20.0000 1.0000 7.0000 0.4676 -0.8812 -0.1648
-2 1 -18 0.0207 -2.0000 1.0000 -18.0000 -0.7062 -0.6242 0.3053

_olex2_submission_special_instructions 'No special instructions were received'
