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

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

data_1a
_database_code_depnum_ccdc_archive 'CCDC 1409609'
_audit_update_record             
;
2015-06-30 deposited with the CCDC.
2015-08-10 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT971_1a                  
;
PROBLEM: Check Calcd Residual Density  0.65A From      I1       2.65 eA-3  
RESPONSE: The large density fluctuations close to iodine are due to the high resolution (theta_max: 52.383) of the data set; tentative truncation of the intensity data to standard resolution resulted in unexceptionally low residual density.
;
# end Validation Reply Form


_audit_creation_date             2015-04-09
_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         'I, Cl, C10 H11 N4 O2 S'
_chemical_formula_sum            'C10 H11 Cl I N4 O2 S'
_chemical_formula_weight         413.64
_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'
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'
Cl Cl 0.1484 0.1585 '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'

_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                   5.6561(6)
_cell_length_b                   11.4126(12)
_cell_length_c                   12.2064(12)
_cell_angle_alpha                116.6140(10)
_cell_angle_beta                 91.131(2)
_cell_angle_gamma                104.114(2)
_cell_volume                     675.58(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.516
_exptl_absorpt_coefficient_mu    2.725
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    2.033
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             402
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0781
_diffrn_reflns_av_unetI/netI     0.0677
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            52171
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         52.383
_diffrn_reflns_theta_min         3.354
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'SMART CCD area detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                11174
_reflns_number_total             15116
_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         2.851
_refine_diff_density_min         -2.267
_refine_diff_density_rms         0.227
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         15116
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0479
_refine_ls_restrained_S_all      1.035
_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)+(0.0441P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1199
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H,H) groups
;
_atom_sites_solution_hydrogens   difmap
_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 0.58942(2) 0.49876(2) 0.10359(2) 0.01645(3) Uani 1 1 d . . . . .
Cl1 Cl 0.73672(7) 0.48460(4) 0.35449(4) 0.01355(5) Uani 1 1 d . . . . .
S1 S 0.65231(6) 1.05445(3) 0.27490(3) 0.00964(5) Uani 1 1 d . . . . .
O1 O 0.4847(2) 1.13865(12) 0.31274(11) 0.01373(16) Uani 1 1 d . . . . .
O2 O 0.9072(2) 1.12276(12) 0.32847(11) 0.01443(17) Uani 1 1 d . . . . .
N1 N 0.6992(2) 0.87384(13) -0.06693(11) 0.01115(15) Uani 1 1 d . . . . .
H1 H 0.607(6) 0.915(3) -0.084(3) 0.013 Uiso 1 1 d R . . . .
N2 N 0.8914(2) 0.85595(13) 0.09550(12) 0.01234(16) Uani 1 1 d . . . . .
N3 N 0.6031(2) 0.98561(12) 0.12642(11) 0.01104(15) Uani 1 1 d . . . . .
N4 N 0.3231(2) 0.63467(13) 0.44716(12) 0.01208(16) Uani 1 1 d . . . . .
H4A H 0.351(6) 0.680(3) 0.533(3) 0.014 Uiso 1 1 d R . . . .
H4B H 0.178(6) 0.592(3) 0.421(3) 0.014 Uiso 1 1 d R . . . .
H4C H 0.404(6) 0.582(3) 0.421(3) 0.014 Uiso 1 1 d R . . . .
C1 C 0.7347(2) 0.90506(13) 0.05562(12) 0.01006(16) Uani 1 1 d . . . . .
C2 C 0.8168(3) 0.79430(15) -0.15112(13) 0.01265(18) Uani 1 1 d . . . . .
H2 H 0.792(6) 0.787(3) -0.227(3) 0.015 Uiso 1 1 d R . . . .
C3 C 0.9793(3) 0.74348(16) -0.11327(14) 0.0147(2) Uani 1 1 d . . . . .
H3 H 1.063(6) 0.697(3) -0.165(3) 0.018 Uiso 1 1 d R . . . .
C4 C 1.0081(3) 0.77750(16) 0.01206(14) 0.0138(2) Uani 1 1 d . . . . .
H4 H 1.129(6) 0.747(4) 0.041(3) 0.017 Uiso 1 1 d R . . . .
C5 C 0.5522(2) 0.92560(13) 0.32055(12) 0.00969(16) Uani 1 1 d . . . . .
C6 C 0.3033(2) 0.85515(15) 0.29677(13) 0.01158(18) Uani 1 1 d . . . . .
H6 H 0.192(6) 0.880(3) 0.255(3) 0.014 Uiso 1 1 d R . . . .
C7 C 0.2265(3) 0.75688(14) 0.33686(13) 0.01192(18) Uani 1 1 d . . . . .
H7 H 0.065(6) 0.704(3) 0.321(3) 0.014 Uiso 1 1 d R . . . .
C8 C 0.4000(2) 0.73559(13) 0.40264(12) 0.01033(16) Uani 1 1 d . . . . .
C9 C 0.6479(3) 0.80766(14) 0.42888(13) 0.01138(17) Uani 1 1 d . . . . .
H9 H 0.763(6) 0.793(3) 0.472(3) 0.014 Uiso 1 1 d R . . . .
C10 C 0.7248(2) 0.90257(14) 0.38554(13) 0.01113(17) Uani 1 1 d . . . . .
H10 H 0.894(6) 0.954(3) 0.402(3) 0.013 Uiso 1 1 d R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.01616(4) 0.01432(4) 0.01622(4) 0.00607(3) 0.00016(3) 0.00210(3)
Cl1 0.01370(13) 0.01351(11) 0.01605(13) 0.00879(10) 0.00360(9) 0.00436(9)
S1 0.01102(12) 0.01052(10) 0.00870(10) 0.00604(9) 0.00133(8) 0.00218(8)
O1 0.0186(5) 0.0136(4) 0.0123(4) 0.0072(3) 0.0041(3) 0.0076(3)
O2 0.0118(4) 0.0163(4) 0.0142(4) 0.0092(3) -0.0010(3) -0.0016(3)
N1 0.0129(4) 0.0138(4) 0.0094(4) 0.0070(3) 0.0029(3) 0.0052(3)
N2 0.0136(4) 0.0142(4) 0.0115(4) 0.0071(3) 0.0016(3) 0.0055(3)
N3 0.0126(4) 0.0143(4) 0.0091(3) 0.0071(3) 0.0028(3) 0.0054(3)
N4 0.0127(4) 0.0128(4) 0.0137(4) 0.0089(3) 0.0030(3) 0.0032(3)
C1 0.0099(4) 0.0115(4) 0.0106(4) 0.0070(3) 0.0016(3) 0.0025(3)
C2 0.0146(5) 0.0144(5) 0.0107(4) 0.0070(4) 0.0041(3) 0.0048(4)
C3 0.0157(6) 0.0167(5) 0.0137(5) 0.0074(4) 0.0039(4) 0.0073(4)
C4 0.0140(5) 0.0158(5) 0.0136(5) 0.0076(4) 0.0023(4) 0.0062(4)
C5 0.0094(4) 0.0116(4) 0.0097(4) 0.0066(3) 0.0010(3) 0.0023(3)
C6 0.0085(4) 0.0147(4) 0.0143(5) 0.0097(4) 0.0000(3) 0.0023(3)
C7 0.0101(4) 0.0140(4) 0.0135(4) 0.0089(4) 0.0003(3) 0.0016(3)
C8 0.0105(4) 0.0112(4) 0.0111(4) 0.0072(3) 0.0015(3) 0.0023(3)
C9 0.0099(4) 0.0137(4) 0.0127(4) 0.0085(4) 0.0003(3) 0.0025(3)
C10 0.0094(4) 0.0133(4) 0.0128(4) 0.0087(4) 0.0004(3) 0.0018(3)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 I1 2.7195(3) 2_665 ?
S1 O1 1.4487(13) . ?
S1 O2 1.4395(12) . ?
S1 N3 1.6053(12) . ?
S1 C5 1.7703(13) . ?
N1 H1 0.86(3) . ?
N1 C1 1.3714(17) . ?
N1 C2 1.3445(19) . ?
N2 C1 1.3437(17) . ?
N2 C4 1.331(2) . ?
N3 C1 1.3392(19) . ?
N4 H4A 0.93(3) . ?
N4 H4B 0.82(3) . ?
N4 H4C 0.80(3) . ?
N4 C8 1.4617(17) . ?
C2 H2 0.90(3) . ?
C2 C3 1.370(2) . ?
C3 H3 0.86(4) . ?
C3 C4 1.395(2) . ?
C4 H4 0.97(4) . ?
C5 C6 1.3915(18) . ?
C5 C10 1.3899(18) . ?
C6 H6 0.97(3) . ?
C6 C7 1.3959(19) . ?
C7 H7 0.92(3) . ?
C7 C8 1.3883(18) . ?
C8 C9 1.3887(19) . ?
C9 H9 0.92(3) . ?
C9 C10 1.3910(18) . ?
C10 H10 0.96(3) . ?

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
O1 S1 N3 103.26(7) . . ?
O1 S1 C5 106.92(7) . . ?
O2 S1 O1 116.08(8) . . ?
O2 S1 N3 114.31(7) . . ?
O2 S1 C5 107.02(6) . . ?
N3 S1 C5 108.89(6) . . ?
C1 N1 H1 115(2) . . ?
C2 N1 H1 123(2) . . ?
C2 N1 C1 122.23(12) . . ?
C4 N2 C1 117.47(12) . . ?
C1 N3 S1 121.80(10) . . ?
H4A N4 H4B 111(3) . . ?
H4A N4 H4C 110(3) . . ?
H4B N4 H4C 109(3) . . ?
C8 N4 H4A 109(2) . . ?
C8 N4 H4B 110(2) . . ?
C8 N4 H4C 108(2) . . ?
N2 C1 N1 120.20(13) . . ?
N3 C1 N1 114.27(12) . . ?
N3 C1 N2 125.54(12) . . ?
N1 C2 H2 115(2) . . ?
N1 C2 C3 119.02(13) . . ?
C3 C2 H2 125(2) . . ?
C2 C3 H3 120(2) . . ?
C2 C3 C4 116.59(14) . . ?
C4 C3 H3 123(2) . . ?
N2 C4 C3 124.48(14) . . ?
N2 C4 H4 118(2) . . ?
C3 C4 H4 118(2) . . ?
C6 C5 S1 119.78(10) . . ?
C10 C5 S1 118.56(10) . . ?
C10 C5 C6 121.58(12) . . ?
C5 C6 H6 117.2(19) . . ?
C5 C6 C7 119.03(12) . . ?
C7 C6 H6 124(2) . . ?
C6 C7 H7 123(2) . . ?
C8 C7 C6 118.87(12) . . ?
C8 C7 H7 118(2) . . ?
C7 C8 N4 119.81(12) . . ?
C7 C8 C9 122.30(12) . . ?
C9 C8 N4 117.89(12) . . ?
C8 C9 H9 122(2) . . ?
C8 C9 C10 118.61(12) . . ?
C10 C9 H9 119(2) . . ?
C5 C10 C9 119.56(12) . . ?
C5 C10 H10 119(2) . . ?
C9 C10 H10 121(2) . . ?

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
N1 H1 N3 0.86(3) 2.03(3) 2.8908(17) 179(3) 2_675
N4 H4A O1 0.93(3) 2.05(3) 2.8589(18) 145(3) 2_676
N4 H4B Cl1 0.82(3) 2.43(3) 3.2495(14) 175(3) 1_455
N4 H4C Cl1 0.80(3) 2.39(4) 3.1635(14) 163(3) .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N3 C1 N1 -169.34(10) . . . . ?
S1 N3 C1 N2 10.5(2) . . . . ?
S1 C5 C6 C7 -178.00(11) . . . . ?
S1 C5 C10 C9 176.13(11) . . . . ?
O1 S1 N3 C1 176.11(11) . . . . ?
O1 S1 C5 C6 46.03(13) . . . . ?
O1 S1 C5 C10 -130.61(12) . . . . ?
O2 S1 N3 C1 49.09(14) . . . . ?
O2 S1 C5 C6 171.03(12) . . . . ?
O2 S1 C5 C10 -5.61(14) . . . . ?
N1 C2 C3 C4 0.9(2) . . . . ?
N3 S1 C5 C6 -64.92(13) . . . . ?
N3 S1 C5 C10 118.44(12) . . . . ?
N4 C8 C9 C10 179.02(13) . . . . ?
C1 N1 C2 C3 -0.6(2) . . . . ?
C1 N2 C4 C3 0.2(2) . . . . ?
C2 N1 C1 N2 0.0(2) . . . . ?
C2 N1 C1 N3 179.91(13) . . . . ?
C2 C3 C4 N2 -0.7(2) . . . . ?
C4 N2 C1 N1 0.1(2) . . . . ?
C4 N2 C1 N3 -179.73(14) . . . . ?
C5 S1 N3 C1 -70.51(13) . . . . ?
C5 C6 C7 C8 2.0(2) . . . . ?
C6 C5 C10 C9 -0.4(2) . . . . ?
C6 C7 C8 N4 179.07(13) . . . . ?
C6 C7 C8 C9 -0.7(2) . . . . ?
C7 C8 C9 C10 -1.2(2) . . . . ?
C8 C9 C10 C5 1.8(2) . . . . ?
C10 C5 C6 C7 -1.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
####################################################################### 
# 
# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 1409610'
_audit_update_record             
;
2015-06-30 deposited with the CCDC.
2015-08-10 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT971_2a                  
;
PROBLEM: Check Calcd Residual Density  0.50A From      I1       3.27 eA-3  
RESPONSE: The large density fluctuations close to iodine are due to the high resolution (theta_max: 52.314) of the data set; tentative truncation of the intensity data to standard resolution resulted in unexceptionally low residual density.
;
# end Validation Reply Form

_audit_creation_date             2015-04-10
_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         'I, Br, C10 H11 N4 O2 S'
_chemical_formula_sum            'C10 H11 Br I N4 O2 S'
_chemical_formula_weight         458.10
_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'
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'
Br Br -0.2901 2.4595 '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'

_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                   5.7185(3)
_cell_length_b                   11.6440(6)
_cell_length_c                   12.3493(6)
_cell_angle_alpha                116.6971(6)
_cell_angle_beta                 91.7117(6)
_cell_angle_gamma                104.1699(7)
_cell_volume                     702.93(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.858
_shelx_estimated_absorpt_T_min   0.419
_exptl_absorpt_coefficient_mu    5.271
_exptl_absorpt_correction_T_max  0.7503
_exptl_absorpt_correction_T_min  0.5431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    2.164
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             438
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            32221
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         52.314
_diffrn_reflns_theta_min         3.313
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'SMART CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                11601
_reflns_number_total             15396
_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         3.150
_refine_diff_density_min         -1.933
_refine_diff_density_rms         0.184
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         15396
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      0.983
_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)+(0.0392P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0965
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H,H) groups
;
_atom_sites_solution_hydrogens   difmap
_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 0.58670(2) 0.49731(2) 0.10306(2) 0.01803(2) Uani 1 1 d . . . A 1
Br1 Br 0.73467(2) 0.48085(2) 0.35361(2) 0.01286(2) Uani 1 1 d . . . . .
S1 S 0.65234(6) 1.05216(3) 0.27278(3) 0.01023(4) Uani 1 1 d . . . . .
O1 O 0.4847(2) 1.13359(10) 0.31024(10) 0.01407(15) Uani 1 1 d . . . . .
O2 O 0.90558(19) 1.12122(11) 0.32689(10) 0.01508(16) Uani 1 1 d . . . . .
N1 N 0.6984(2) 0.87734(11) -0.06549(10) 0.01159(15) Uani 1 1 d . . . . .
H1 H 0.590(4) 0.920(2) -0.091(2) 0.014 Uiso 1 1 d R . . . .
N2 N 0.8863(2) 0.85753(12) 0.09559(11) 0.01331(16) Uani 1 1 d . . . . .
N3 N 0.6019(2) 0.98487(11) 0.12561(10) 0.01152(15) Uani 1 1 d . . . . .
N4 N 0.3318(2) 0.64853(11) 0.45163(12) 0.01295(16) Uani 1 1 d . . . . .
H4A H 0.369(4) 0.694(2) 0.530(2) 0.016 Uiso 1 1 d R . . . .
H4B H 0.170(4) 0.600(2) 0.429(2) 0.016 Uiso 1 1 d R . . . .
H4C H 0.425(4) 0.591(2) 0.428(2) 0.016 Uiso 1 1 d R . . . .
C1 C 0.7324(2) 0.90688(12) 0.05588(11) 0.01045(16) Uani 1 1 d . . . . .
C2 C 0.8163(2) 0.80052(13) -0.14801(13) 0.01328(18) Uani 1 1 d . . . . .
H2 H 0.782(4) 0.781(2) -0.223(2) 0.016 Uiso 1 1 d R . . . .
C3 C 0.9744(3) 0.74894(15) -0.11061(14) 0.0154(2) Uani 1 1 d . . . . .
H3 H 1.066(4) 0.697(2) -0.168(2) 0.019 Uiso 1 1 d R . . . .
C4 C 1.0006(3) 0.78071(14) 0.01340(14) 0.0151(2) Uani 1 1 d . . . . .
H4 H 1.110(4) 0.748(2) 0.043(2) 0.018 Uiso 1 1 d R . . . .
C5 C 0.5561(2) 0.92606(12) 0.31807(11) 0.01054(16) Uani 1 1 d . . . . .
C6 C 0.3087(2) 0.85722(13) 0.29572(13) 0.01248(18) Uani 1 1 d . . . . .
H6 H 0.194(4) 0.880(2) 0.261(2) 0.015 Uiso 1 1 d R . . . .
C7 C 0.2343(2) 0.76295(13) 0.33732(13) 0.01289(18) Uani 1 1 d . . . . .
H7 H 0.068(4) 0.711(2) 0.321(2) 0.015 Uiso 1 1 d R . . . .
C8 C 0.4073(2) 0.74363(12) 0.40344(12) 0.01085(16) Uani 1 1 d . . . . .
C9 C 0.6537(2) 0.81352(13) 0.42808(13) 0.01191(17) Uani 1 1 d . . . . .
H9 H 0.762(4) 0.799(2) 0.477(2) 0.014 Uiso 1 1 d R . . . .
C10 C 0.7282(2) 0.90439(13) 0.38321(12) 0.01192(17) Uani 1 1 d . . . . .
H10 H 0.881(4) 0.954(2) 0.395(2) 0.014 Uiso 1 1 d R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.01805(4) 0.01609(4) 0.01708(4) 0.00714(3) -0.00108(3) 0.00193(3)
Br1 0.01280(5) 0.01299(5) 0.01537(5) 0.00846(4) 0.00251(4) 0.00446(4)
S1 0.01104(10) 0.01101(10) 0.00999(10) 0.00636(8) 0.00056(8) 0.00275(8)
O1 0.0183(4) 0.0139(3) 0.0131(4) 0.0073(3) 0.0032(3) 0.0077(3)
O2 0.0125(3) 0.0167(4) 0.0149(4) 0.0094(3) -0.0019(3) -0.0011(3)
N1 0.0123(4) 0.0142(4) 0.0107(4) 0.0072(3) 0.0020(3) 0.0053(3)
N2 0.0135(4) 0.0157(4) 0.0139(4) 0.0086(3) 0.0010(3) 0.0063(3)
N3 0.0124(4) 0.0145(4) 0.0097(3) 0.0068(3) 0.0014(3) 0.0051(3)
N4 0.0139(4) 0.0126(4) 0.0144(4) 0.0081(3) 0.0019(3) 0.0037(3)
C1 0.0100(4) 0.0120(4) 0.0111(4) 0.0070(3) 0.0009(3) 0.0033(3)
C2 0.0133(4) 0.0154(4) 0.0125(4) 0.0074(4) 0.0028(4) 0.0046(4)
C3 0.0154(5) 0.0176(5) 0.0154(5) 0.0075(4) 0.0038(4) 0.0085(4)
C4 0.0150(5) 0.0162(5) 0.0161(5) 0.0080(4) 0.0006(4) 0.0072(4)
C5 0.0101(4) 0.0119(4) 0.0110(4) 0.0068(3) 0.0005(3) 0.0029(3)
C6 0.0104(4) 0.0151(4) 0.0147(5) 0.0094(4) 0.0003(3) 0.0037(3)
C7 0.0107(4) 0.0145(4) 0.0156(5) 0.0095(4) 0.0001(4) 0.0026(3)
C8 0.0112(4) 0.0107(4) 0.0119(4) 0.0067(3) 0.0008(3) 0.0027(3)
C9 0.0105(4) 0.0135(4) 0.0144(5) 0.0090(4) -0.0002(3) 0.0032(3)
C10 0.0098(4) 0.0145(4) 0.0132(4) 0.0084(4) -0.0005(3) 0.0030(3)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 I1 2.7368(2) 2_665 ?
S1 O1 1.4523(11) . ?
S1 O2 1.4421(10) . ?
S1 N3 1.6058(11) . ?
S1 C5 1.7698(12) . ?
N1 H1 1.00(2) . ?
N1 C1 1.3746(16) . ?
N1 C2 1.3457(18) . ?
N2 C1 1.3488(16) . ?
N2 C4 1.3295(19) . ?
N3 C1 1.3385(17) . ?
N4 H4A 0.85(2) . ?
N4 H4B 0.92(2) . ?
N4 H4C 0.91(2) . ?
N4 C8 1.4629(16) . ?
C2 H2 0.86(2) . ?
C2 C3 1.3718(19) . ?
C3 H3 0.96(2) . ?
C3 C4 1.398(2) . ?
C4 H4 0.95(2) . ?
C5 C6 1.3939(17) . ?
C5 C10 1.3914(16) . ?
C6 H6 0.92(2) . ?
C6 C7 1.3932(18) . ?
C7 H7 0.95(2) . ?
C7 C8 1.3863(17) . ?
C8 C9 1.3897(17) . ?
C9 H9 0.95(2) . ?
C9 C10 1.3886(17) . ?
C10 H10 0.89(2) . ?

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
O1 S1 N3 103.26(6) . . ?
O1 S1 C5 106.55(6) . . ?
O2 S1 O1 115.96(7) . . ?
O2 S1 N3 114.27(6) . . ?
O2 S1 C5 107.08(6) . . ?
N3 S1 C5 109.39(6) . . ?
C1 N1 H1 118.2(13) . . ?
C2 N1 H1 119.6(13) . . ?
C2 N1 C1 122.07(11) . . ?
C4 N2 C1 117.49(12) . . ?
C1 N3 S1 121.67(9) . . ?
H4A N4 H4B 111(2) . . ?
H4A N4 H4C 106(2) . . ?
H4B N4 H4C 109(2) . . ?
C8 N4 H4A 106.4(16) . . ?
C8 N4 H4B 115.1(14) . . ?
C8 N4 H4C 109.2(15) . . ?
N2 C1 N1 120.15(12) . . ?
N3 C1 N1 114.43(10) . . ?
N3 C1 N2 125.42(12) . . ?
N1 C2 H2 118.1(15) . . ?
N1 C2 C3 119.26(13) . . ?
C3 C2 H2 122.5(15) . . ?
C2 C3 H3 120.4(14) . . ?
C2 C3 C4 116.43(13) . . ?
C4 C3 H3 123.1(14) . . ?
N2 C4 C3 124.59(12) . . ?
N2 C4 H4 116.2(15) . . ?
C3 C4 H4 119.2(15) . . ?
C6 C5 S1 119.73(9) . . ?
C10 C5 S1 118.88(9) . . ?
C10 C5 C6 121.23(11) . . ?
C5 C6 H6 120.6(15) . . ?
C7 C6 C5 119.08(11) . . ?
C7 C6 H6 120.0(15) . . ?
C6 C7 H7 121.4(14) . . ?
C8 C7 C6 119.04(11) . . ?
C8 C7 H7 119.6(14) . . ?
C7 C8 N4 119.93(11) . . ?
C7 C8 C9 122.28(11) . . ?
C9 C8 N4 117.79(11) . . ?
C8 C9 H9 118.3(14) . . ?
C10 C9 C8 118.48(11) . . ?
C10 C9 H9 123.2(14) . . ?
C5 C10 H10 115.0(15) . . ?
C9 C10 C5 119.84(11) . . ?
C9 C10 H10 125.1(15) . . ?

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
N1 H1 N3 1.00(2) 1.90(2) 2.9010(15) 174(2) 2_675
N4 H4A O1 0.85(2) 2.04(2) 2.8274(16) 154(2) 2_676
N4 H4B Br1 0.92(2) 2.45(2) 3.3618(12) 174(2) 1_455
N4 H4C Br1 0.91(2) 2.40(2) 3.2910(12) 165(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
S1 N3 C1 N1 -168.64(9) . . . . ?
S1 N3 C1 N2 11.78(18) . . . . ?
S1 C5 C6 C7 -176.83(11) . . . . ?
S1 C5 C10 C9 174.91(11) . . . . ?
O1 S1 N3 C1 176.30(10) . . . . ?
O1 S1 C5 C6 45.05(12) . . . . ?
O1 S1 C5 C10 -130.47(11) . . . . ?
O2 S1 N3 C1 49.46(12) . . . . ?
O2 S1 C5 C6 169.73(11) . . . . ?
O2 S1 C5 C10 -5.79(13) . . . . ?
N1 C2 C3 C4 0.2(2) . . . . ?
N3 S1 C5 C6 -65.94(12) . . . . ?
N3 S1 C5 C10 118.54(11) . . . . ?
N4 C8 C9 C10 -179.85(12) . . . . ?
C1 N1 C2 C3 0.50(19) . . . . ?
C1 N2 C4 C3 0.7(2) . . . . ?
C2 N1 C1 N2 -0.63(19) . . . . ?
C2 N1 C1 N3 179.77(12) . . . . ?
C2 C3 C4 N2 -0.9(2) . . . . ?
C4 N2 C1 N1 0.00(18) . . . . ?
C4 N2 C1 N3 179.57(13) . . . . ?
C5 S1 N3 C1 -70.55(11) . . . . ?
C5 C6 C7 C8 2.2(2) . . . . ?
C6 C5 C10 C9 -0.5(2) . . . . ?
C6 C7 C8 N4 177.88(13) . . . . ?
C6 C7 C8 C9 -1.1(2) . . . . ?
C7 C8 C9 C10 -0.9(2) . . . . ?
C8 C9 C10 C5 1.7(2) . . . . ?
C10 C5 C6 C7 -1.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
####################################################################### 
# 
# 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_2b
_database_code_depnum_ccdc_archive 'CCDC 1409611'
_audit_update_record             
;
2015-06-30 deposited with the CCDC.
2015-08-10 downloaded from the CCDC.
;
_audit_creation_date             2015-06-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H11 N4 O2 S, C H3 O, Br'
_chemical_formula_sum            'C11 H14 Br N4 O3 S'
_chemical_formula_weight         362.23
_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'
Br Br -0.2901 2.4595 '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                   5.7078(5)
_cell_length_b                   11.5383(10)
_cell_length_c                   12.1980(10)
_cell_angle_alpha                62.8640(10)
_cell_angle_beta                 79.4180(12)
_cell_angle_gamma                76.9800(12)
_cell_volume                     693.50(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3215
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      30.14
_cell_measurement_theta_min      3.42
_shelx_estimated_absorpt_T_max   0.669
_shelx_estimated_absorpt_T_min   0.434
_exptl_absorpt_coefficient_mu    3.127
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.5549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1365 before and 0.0419 after correction.
The Ratio of minimum to maximum transmission is 0.7436.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             366
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10816
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         3.298
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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                3652
_reflns_number_total             4018
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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         1.748
_refine_diff_density_min         -1.003
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         4018
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.053
_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)+(0.0325P)²+0.9881P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0848
_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 O(H) groups
2.a Riding coordinates:
 O3(H3A), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C2(H2), C6(H6), C7(H7), C9(H9), C10(H10)
;
_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 0.10198(10) 0.77756(5) 0.27242(5) 0.01216(11) Uani 1 1 d . . . . .
O1 O -0.1461(3) 0.81773(17) 0.31178(16) 0.0159(3) Uani 1 1 d . . . . .
O2 O 0.2853(3) 0.79408(17) 0.32874(16) 0.0170(3) Uani 1 1 d . . . . .
N1 N 0.3167(4) 0.94391(19) -0.06698(18) 0.0128(4) Uani 1 1 d . . . . .
N3 N 0.1157(4) 0.85815(19) 0.12492(17) 0.0132(4) Uani 1 1 d . . . . .
N4 N 0.1814(4) 0.1965(2) 0.4493(2) 0.0137(4) Uani 1 1 d . . . . .
H4A H 0.165(6) 0.166(4) 0.527(4) 0.031(9) Uiso 1 1 d . . . . .
H4B H 0.312(7) 0.162(4) 0.427(4) 0.039(10) Uiso 1 1 d . . . . .
H4C H 0.059(8) 0.177(4) 0.428(4) 0.043(11) Uiso 1 1 d . . . . .
N2 N 0.5236(4) 0.7622(2) 0.09207(19) 0.0154(4) Uani 1 1 d . . . . .
C3 C 0.7135(4) 0.8609(2) -0.1167(2) 0.0174(5) Uani 1 1 d . . . . .
H3 H 0.8520 0.8620 -0.1737 0.021 Uiso 1 1 calc R . . . .
C4 C 0.7113(5) 0.7686(2) 0.0070(2) 0.0177(5) Uani 1 1 d . . . . .
H4 H 0.8534 0.7058 0.0326 0.021 Uiso 1 1 calc R . . . .
C1 C 0.3227(4) 0.8508(2) 0.0536(2) 0.0130(4) Uani 1 1 d . . . . .
C2 C 0.5060(4) 0.9500(2) -0.1519(2) 0.0150(4) Uani 1 1 d . . . . .
H2 H 0.4962 1.0149 -0.2351 0.018 Uiso 1 1 calc R . . . .
C5 C 0.1328(4) 0.6067(2) 0.3148(2) 0.0120(4) Uani 1 1 d . . . . .
C6 C -0.0457(4) 0.5586(2) 0.2912(2) 0.0145(4) Uani 1 1 d . . . . .
H6 H -0.1783 0.6173 0.2477 0.017 Uiso 1 1 calc R . . . .
C7 C -0.0267(4) 0.4225(2) 0.3325(2) 0.0150(4) Uani 1 1 d . . . . .
H7 H -0.1436 0.3875 0.3154 0.018 Uiso 1 1 calc R . . . .
C8 C 0.1650(4) 0.3397(2) 0.3989(2) 0.0128(4) Uani 1 1 d . . . . .
C9 C 0.3424(4) 0.3870(2) 0.4236(2) 0.0147(4) Uani 1 1 d . . . . .
H9 H 0.4716 0.3279 0.4699 0.018 Uiso 1 1 calc R . . . .
C10 C 0.3272(4) 0.5225(2) 0.3793(2) 0.0141(4) Uani 1 1 d . . . . .
H10 H 0.4489 0.5574 0.3931 0.017 Uiso 1 1 calc R . . . .
O3 O 0.7166(5) 0.3483(2) 0.0648(2) 0.0409(6) Uani 1 1 d . . . . .
H3A H 0.7121 0.2841 0.1443 0.061 Uiso 1 1 d R . . . .
C11 C 0.5187(8) 0.4440(4) 0.0692(3) 0.0477(10) Uani 1 1 d . . . . .
H11A H 0.5721 0.4850 0.1144 0.057 Uiso 1 1 d R . . . .
H11B H 0.3717 0.4066 0.0906 0.057 Uiso 1 1 d R . . . .
Br1 Br 0.74542(4) 0.12280(2) 0.35540(2) 0.01531(7) Uani 1 1 d . . . . .
H1 H 0.189(6) 1.000(3) -0.083(3) 0.024(8) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0147(3) 0.0088(2) 0.0113(2) -0.0026(2) -0.00214(19) -0.00191(19)
O1 0.0169(8) 0.0131(8) 0.0148(8) -0.0050(6) 0.0008(6) -0.0007(6)
O2 0.0222(9) 0.0133(8) 0.0158(8) -0.0040(7) -0.0060(7) -0.0051(7)
N1 0.0122(9) 0.0101(9) 0.0138(9) -0.0033(7) -0.0020(7) -0.0012(7)
N3 0.0148(9) 0.0110(9) 0.0105(9) -0.0014(7) -0.0011(7) -0.0029(7)
N4 0.0149(10) 0.0104(9) 0.0151(10) -0.0051(8) -0.0012(8) -0.0016(7)
N2 0.0145(10) 0.0138(9) 0.0159(9) -0.0043(8) -0.0019(7) -0.0025(7)
C3 0.0154(11) 0.0184(11) 0.0167(11) -0.0064(9) 0.0007(9) -0.0042(9)
C4 0.0157(11) 0.0160(11) 0.0196(12) -0.0061(9) -0.0027(9) -0.0018(9)
C1 0.0156(11) 0.0091(10) 0.0137(10) -0.0033(8) -0.0029(8) -0.0029(8)
C2 0.0183(11) 0.0136(10) 0.0132(10) -0.0044(8) -0.0002(8) -0.0067(9)
C5 0.0134(10) 0.0096(10) 0.0107(10) -0.0028(8) -0.0005(8) -0.0013(8)
C6 0.0145(11) 0.0124(10) 0.0153(10) -0.0046(8) -0.0036(8) -0.0014(8)
C7 0.0152(11) 0.0137(11) 0.0157(11) -0.0052(9) -0.0031(8) -0.0031(8)
C8 0.0148(11) 0.0091(10) 0.0125(10) -0.0038(8) -0.0005(8) -0.0007(8)
C9 0.0136(11) 0.0135(10) 0.0146(10) -0.0037(9) -0.0042(8) -0.0003(8)
C10 0.0137(11) 0.0137(10) 0.0142(10) -0.0045(9) -0.0033(8) -0.0027(8)
O3 0.0414(14) 0.0357(13) 0.0320(12) -0.0019(10) -0.0094(10) -0.0043(11)
C11 0.056(2) 0.061(2) 0.048(2) -0.039(2) 0.0193(18) -0.033(2)
Br1 0.01383(12) 0.01318(12) 0.01918(12) -0.00742(9) -0.00098(8) -0.00224(8)

_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 O1 1.4519(18) . ?
S1 O2 1.4411(18) . ?
S1 N3 1.601(2) . ?
S1 C5 1.770(2) . ?
N1 C1 1.371(3) . ?
N1 C2 1.343(3) . ?
N1 H1 0.85(3) . ?
N3 C1 1.343(3) . ?
N4 H4A 0.84(4) . ?
N4 H4B 0.82(4) . ?
N4 H4C 0.89(4) . ?
N4 C8 1.463(3) . ?
N2 C4 1.337(3) . ?
N2 C1 1.346(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.394(3) . ?
C3 C2 1.371(3) . ?
C4 H4 0.9500 . ?
C2 H2 0.9500 . ?
C5 C6 1.392(3) . ?
C5 C10 1.390(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.397(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.384(3) . ?
C8 C9 1.387(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.389(3) . ?
C10 H10 0.9500 . ?
O3 H3A 0.9137 . ?
O3 C11 1.402(5) . ?
C11 C11 1.608(8) 2_665 ?
C11 H11A 0.9931 . ?
C11 H11B 0.9687 . ?

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
O1 S1 N3 103.28(10) . . ?
O1 S1 C5 106.02(10) . . ?
O2 S1 O1 115.93(11) . . ?
O2 S1 N3 114.46(11) . . ?
O2 S1 C5 106.99(11) . . ?
N3 S1 C5 109.81(10) . . ?
C1 N1 H1 116(2) . . ?
C2 N1 C1 122.3(2) . . ?
C2 N1 H1 122(2) . . ?
C1 N3 S1 121.45(17) . . ?
H4A N4 H4B 110(3) . . ?
H4A N4 H4C 107(3) . . ?
H4B N4 H4C 111(4) . . ?
C8 N4 H4A 107(2) . . ?
C8 N4 H4B 112(3) . . ?
C8 N4 H4C 110(3) . . ?
C4 N2 C1 116.8(2) . . ?
C4 C3 H3 121.7 . . ?
C2 C3 H3 121.7 . . ?
C2 C3 C4 116.7(2) . . ?
N2 C4 C3 124.7(2) . . ?
N2 C4 H4 117.7 . . ?
C3 C4 H4 117.7 . . ?
N3 C1 N1 114.1(2) . . ?
N3 C1 N2 125.3(2) . . ?
N2 C1 N1 120.6(2) . . ?
N1 C2 C3 118.9(2) . . ?
N1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C6 C5 S1 119.64(17) . . ?
C10 C5 S1 118.63(18) . . ?
C10 C5 C6 121.6(2) . . ?
C5 C6 H6 120.5 . . ?
C5 C6 C7 118.9(2) . . ?
C7 C6 H6 120.5 . . ?
C6 C7 H7 120.5 . . ?
C8 C7 C6 118.9(2) . . ?
C8 C7 H7 120.5 . . ?
C7 C8 N4 120.0(2) . . ?
C7 C8 C9 122.4(2) . . ?
C9 C8 N4 117.7(2) . . ?
C8 C9 H9 120.7 . . ?
C8 C9 C10 118.7(2) . . ?
C10 C9 H9 120.7 . . ?
C5 C10 H10 120.2 . . ?
C9 C10 C5 119.5(2) . . ?
C9 C10 H10 120.2 . . ?
C11 O3 H3A 102.8 . . ?
O3 C11 C11 108.8(3) . 2_665 ?
O3 C11 H11A 104.2 . . ?
O3 C11 H11B 109.1 . . ?
C11 C11 H11A 107.3 2_665 . ?
C11 C11 H11B 101.4 2_665 . ?
H11A C11 H11B 125.4 . . ?

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
S1 N3 C1 N1 -168.04(16) . . . . ?
S1 N3 C1 N2 12.0(3) . . . . ?
S1 C5 C6 C7 -175.77(18) . . . . ?
S1 C5 C10 C9 173.94(18) . . . . ?
O1 S1 N3 C1 177.64(18) . . . . ?
O1 S1 C5 C6 44.9(2) . . . . ?
O1 S1 C5 C10 -130.41(19) . . . . ?
O2 S1 N3 C1 50.7(2) . . . . ?
O2 S1 C5 C6 169.14(18) . . . . ?
O2 S1 C5 C10 -6.1(2) . . . . ?
N3 S1 C5 C6 -66.1(2) . . . . ?
N3 S1 C5 C10 118.64(19) . . . . ?
N4 C8 C9 C10 -178.4(2) . . . . ?
C4 N2 C1 N1 -1.2(3) . . . . ?
C4 N2 C1 N3 178.8(2) . . . . ?
C4 C3 C2 N1 0.4(3) . . . . ?
C1 N1 C2 C3 -0.7(3) . . . . ?
C1 N2 C4 C3 0.9(4) . . . . ?
C2 N1 C1 N3 -178.8(2) . . . . ?
C2 N1 C1 N2 1.2(3) . . . . ?
C2 C3 C4 N2 -0.5(4) . . . . ?
C5 S1 N3 C1 -69.6(2) . . . . ?
C5 C6 C7 C8 2.0(3) . . . . ?
C6 C5 C10 C9 -1.2(4) . . . . ?
C6 C7 C8 N4 176.5(2) . . . . ?
C6 C7 C8 C9 -1.5(4) . . . . ?
C7 C8 C9 C10 -0.4(4) . . . . ?
C8 C9 C10 C5 1.7(3) . . . . ?
C10 C5 C6 C7 -0.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeOH and ethylene glycol'
####################################################################### 
# 
# 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_2c
_database_code_depnum_ccdc_archive 'CCDC 1409612'
_audit_update_record             
;
2015-06-30 deposited with the CCDC.
2015-08-10 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT223_2c                  
;
PROBLEM: Large Solvent/Anion H Ueq(max)/Ueq(min) ..... 4.3 Ratio
RESPONSE: The ethanol solvent molecule is disordered.
;
# end Validation Reply Form


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C10 H11 N4 O2 S), C2 H6 O, 2(Br)'
_chemical_formula_sum            'C22 H28 Br2 N8 O5 S2'
_chemical_formula_weight         708.46

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.709(3)
_cell_length_b                   11.532(6)
_cell_length_c                   12.116(6)
_cell_angle_alpha                62.675(8)
_cell_angle_beta                 79.693(9)
_cell_angle_gamma                77.507(9)
_cell_volume                     689.0(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    638
_cell_measurement_theta_min      3.4360
_cell_measurement_theta_max      19.3433

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             358
_exptl_absorpt_coefficient_mu    3.143
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5866
_exptl_absorpt_correction_T_max  0.9398
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Incoatec microsource'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8218
_diffrn_reflns_av_R_equivalents  0.0916
_diffrn_reflns_av_sigmaI/netI    0.1053
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         26.57
_reflns_number_total             2849
_reflns_number_gt                2084
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0442P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2849
_refine_ls_number_parameters     190
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1182
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.24558(9) 0.87643(5) 0.14855(5) 0.02360(18) Uani 1 1 d . . .
S1 S 0.4022(2) 0.22411(12) 0.22589(12) 0.0188(3) Uani 1 1 d . . .
O1 O 0.6485(6) 0.1857(3) 0.1867(3) 0.0217(8) Uani 1 1 d . . .
O2 O 0.2204(6) 0.2069(3) 0.1691(3) 0.0228(8) Uani 1 1 d . . .
N1 N 0.1847(7) 0.0547(4) 0.5662(4) 0.0178(9) Uani 1 1 d . . .
H1A H 0.3172 -0.0056 0.5901 0.021 Uiso 1 1 d R . .
N2 N -0.0199(7) 0.2376(4) 0.4070(4) 0.0208(10) Uani 1 1 d . . .
N3 N 0.3867(7) 0.1427(4) 0.3749(4) 0.0186(9) Uani 1 1 d . . .
N4 N 0.3155(7) 0.8054(4) 0.0530(4) 0.0193(9) Uani 1 1 d . . .
H4A H 0.3248 0.8333 -0.0318 0.023 Uiso 1 1 d R . .
H4B H 0.4467 0.8229 0.0736 0.023 Uiso 1 1 d R . .
H4C H 0.1743 0.8412 0.0794 0.023 Uiso 1 1 d R . .
C1 C 0.1797(9) 0.1487(5) 0.4463(5) 0.0172(11) Uani 1 1 d . . .
C2 C -0.0040(9) 0.0468(5) 0.6519(5) 0.0213(12) Uani 1 1 d . . .
H2 H 0.0049 -0.0193 0.7355 0.026 Uiso 1 1 calc R . .
C3 C -0.2111(9) 0.1366(5) 0.6159(5) 0.0217(12) Uani 1 1 d . . .
H3 H -0.3493 0.1352 0.6731 0.026 Uiso 1 1 calc R . .
C4 C -0.2073(9) 0.2289(5) 0.4923(5) 0.0249(13) Uani 1 1 d . . .
H4 H -0.3493 0.2909 0.4660 0.030 Uiso 1 1 calc R . .
C5 C 0.3710(9) 0.3951(5) 0.1838(5) 0.0194(11) Uani 1 1 d . . .
C6 C 0.1774(9) 0.4779(5) 0.1214(5) 0.0216(12) Uani 1 1 d . . .
H6 H 0.0557 0.4425 0.1077 0.026 Uiso 1 1 calc R . .
C7 C 0.1597(9) 0.6135(5) 0.0783(5) 0.0195(11) Uani 1 1 d . . .
H7 H 0.0286 0.6719 0.0332 0.023 Uiso 1 1 calc R . .
C8 C 0.3354(9) 0.6613(5) 0.1021(5) 0.0184(11) Uani 1 1 d . . .
C9 C 0.5263(9) 0.5801(5) 0.1670(5) 0.0201(12) Uani 1 1 d . . .
H9 H 0.6425 0.6157 0.1846 0.024 Uiso 1 1 calc R . .
C10 C 0.5476(9) 0.4447(5) 0.2069(5) 0.0206(12) Uani 1 1 d . . .
H10 H 0.6818 0.3869 0.2494 0.025 Uiso 1 1 calc R . .
O3 O -0.2360(15) 0.6560(8) 0.4401(9) 0.051(3) Uani 0.50 1 d PD A -1
H3O H -0.2560 0.7147 0.3671 0.076 Uiso 0.50 1 calc PR A -1
C11 C -0.040(2) 0.5526(11) 0.4364(14) 0.033(3) Uani 0.50 1 d PDU A -1
H111 H -0.0824 0.5101 0.3868 0.040 Uiso 0.50 1 d PR A -1
H112 H 0.1104 0.5879 0.3958 0.040 Uiso 0.50 1 d PR A -1
C12 C -0.077(5) 0.481(3) 0.553(3) 0.141(11) Uani 0.50 1 d PU A -1
H121 H -0.2252 0.4437 0.5684 0.170 Uiso 0.50 1 d PR A -1
H122 H -0.0839 0.5209 0.6128 0.170 Uiso 0.50 1 d PR A -1
H123 H 0.0669 0.4121 0.5630 0.170 Uiso 0.50 1 d PR A -1

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0127(3) 0.0243(3) 0.0348(3) -0.0139(2) -0.0021(2) -0.0027(2)
S1 0.0142(7) 0.0174(7) 0.0218(7) -0.0053(6) -0.0027(5) -0.0033(5)
O1 0.0150(19) 0.0204(19) 0.025(2) -0.0073(16) 0.0010(16) -0.0026(15)
O2 0.018(2) 0.0212(19) 0.026(2) -0.0043(16) -0.0085(16) -0.0056(15)
N1 0.011(2) 0.020(2) 0.021(2) -0.0075(19) -0.0028(18) -0.0015(17)
N2 0.009(2) 0.020(2) 0.027(3) -0.004(2) -0.0011(19) -0.0034(18)
N3 0.015(2) 0.018(2) 0.020(2) -0.0042(19) -0.0010(18) -0.0047(18)
N4 0.014(2) 0.018(2) 0.024(2) -0.0080(19) -0.0014(19) -0.0030(18)
C1 0.010(3) 0.016(3) 0.023(3) -0.003(2) -0.003(2) -0.006(2)
C2 0.020(3) 0.020(3) 0.022(3) -0.007(2) -0.001(2) -0.006(2)
C3 0.011(3) 0.025(3) 0.030(3) -0.013(2) -0.001(2) -0.004(2)
C4 0.015(3) 0.024(3) 0.032(3) -0.009(3) -0.006(2) 0.001(2)
C5 0.018(3) 0.017(3) 0.021(3) -0.006(2) -0.001(2) -0.005(2)
C6 0.018(3) 0.021(3) 0.024(3) -0.007(2) -0.007(2) -0.002(2)
C7 0.011(3) 0.024(3) 0.022(3) -0.009(2) -0.006(2) 0.002(2)
C8 0.014(3) 0.019(3) 0.021(3) -0.008(2) -0.001(2) -0.004(2)
C9 0.014(3) 0.022(3) 0.023(3) -0.007(2) -0.003(2) -0.005(2)
C10 0.011(3) 0.022(3) 0.021(3) -0.004(2) -0.003(2) 0.001(2)
O3 0.029(5) 0.047(6) 0.056(6) -0.008(5) -0.006(5) 0.003(4)
C11 0.042(5) 0.029(5) 0.033(5) -0.014(4) -0.016(4) -0.001(4)
C12 0.144(12) 0.140(12) 0.144(12) -0.067(7) -0.007(5) -0.024(5)

_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 1.436(4) . ?
S1 O1 1.443(4) . ?
S1 N3 1.604(4) . ?
S1 C5 1.771(5) . ?
N1 C2 1.342(6) . ?
N1 C1 1.357(6) . ?
N1 H1A 0.8973 . ?
N2 C4 1.334(6) . ?
N2 C1 1.348(6) . ?
N3 C1 1.343(6) . ?
N4 C8 1.471(6) . ?
N4 H4A 0.9194 . ?
N4 H4B 0.9181 . ?
N4 H4C 0.8984 . ?
C2 C3 1.379(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(7) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C5 C6 1.373(7) . ?
C5 C10 1.385(7) . ?
C6 C7 1.389(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.373(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.369(7) . ?
C9 C10 1.390(7) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
O3 C11 1.461(5) . ?
O3 H3O 0.8400 . ?
C11 C12 1.28(2) . ?
C11 H111 1.0164 . ?
C11 H112 0.9788 . ?
C12 H121 0.9772 . ?
C12 H122 1.0141 . ?
C12 H123 0.9926 . ?

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 O1 116.0(2) . . ?
O2 S1 N3 114.2(2) . . ?
O1 S1 N3 103.6(2) . . ?
O2 S1 C5 107.2(2) . . ?
O1 S1 C5 106.0(2) . . ?
N3 S1 C5 109.6(2) . . ?
C2 N1 C1 122.4(4) . . ?
C2 N1 H1A 117.9 . . ?
C1 N1 H1A 119.7 . . ?
C4 N2 C1 116.4(4) . . ?
C1 N3 S1 121.6(4) . . ?
C8 N4 H4A 102.6 . . ?
C8 N4 H4B 108.0 . . ?
H4A N4 H4B 110.2 . . ?
C8 N4 H4C 112.1 . . ?
H4A N4 H4C 110.2 . . ?
H4B N4 H4C 113.2 . . ?
N3 C1 N2 125.2(5) . . ?
N3 C1 N1 113.9(4) . . ?
N2 C1 N1 121.0(5) . . ?
N1 C2 C3 118.6(5) . . ?
N1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C2 C3 C4 116.6(5) . . ?
C2 C3 H3 121.7 . . ?
C4 C3 H3 121.7 . . ?
N2 C4 C3 125.1(5) . . ?
N2 C4 H4 117.5 . . ?
C3 C4 H4 117.5 . . ?
C6 C5 C10 120.9(5) . . ?
C6 C5 S1 118.8(4) . . ?
C10 C5 S1 120.2(4) . . ?
C5 C6 C7 119.9(5) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 118.6(5) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
C9 C8 C7 122.3(5) . . ?
C9 C8 N4 120.1(4) . . ?
C7 C8 N4 117.6(4) . . ?
C8 C9 C10 119.0(5) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C5 C10 C9 119.3(5) . . ?
C5 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C11 O3 H3O 109.5 . . ?
C12 C11 O3 92.1(16) . . ?
C12 C11 H111 110.4 . . ?
O3 C11 H111 109.7 . . ?
C12 C11 H112 124.2 . . ?
O3 C11 H112 111.7 . . ?
H111 C11 H112 107.4 . . ?
C11 C12 H121 108.7 . . ?
C11 C12 H122 118.6 . . ?
H121 C12 H122 109.3 . . ?
C11 C12 H123 98.2 . . ?
H121 C12 H123 111.1 . . ?
H122 C12 H123 110.7 . . ?

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
O2 S1 N3 C1 -50.6(4) . . . . ?
O1 S1 N3 C1 -177.6(4) . . . . ?
C5 S1 N3 C1 69.6(4) . . . . ?
S1 N3 C1 N2 -12.6(7) . . . . ?
S1 N3 C1 N1 167.2(3) . . . . ?
C4 N2 C1 N3 -179.2(5) . . . . ?
C4 N2 C1 N1 1.1(7) . . . . ?
C2 N1 C1 N3 178.7(4) . . . . ?
C2 N1 C1 N2 -1.6(7) . . . . ?
C1 N1 C2 C3 0.9(7) . . . . ?
N1 C2 C3 C4 0.1(7) . . . . ?
C1 N2 C4 C3 -0.1(8) . . . . ?
C2 C3 C4 N2 -0.5(8) . . . . ?
O2 S1 C5 C6 7.2(5) . . . . ?
O1 S1 C5 C6 131.7(4) . . . . ?
N3 S1 C5 C6 -117.2(4) . . . . ?
O2 S1 C5 C10 -168.7(4) . . . . ?
O1 S1 C5 C10 -44.3(5) . . . . ?
N3 S1 C5 C10 66.9(5) . . . . ?
C10 C5 C6 C7 1.3(8) . . . . ?
S1 C5 C6 C7 -174.6(4) . . . . ?
C5 C6 C7 C8 -1.5(8) . . . . ?
C6 C7 C8 C9 -0.2(8) . . . . ?
C6 C7 C8 N4 178.7(4) . . . . ?
C7 C8 C9 C10 2.1(8) . . . . ?
N4 C8 C9 C10 -176.7(4) . . . . ?
C6 C5 C10 C9 0.6(8) . . . . ?
S1 C5 C10 C9 176.5(4) . . . . ?
C8 C9 C10 C5 -2.3(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        26.57
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.702
_refine_diff_density_min         -0.764
_refine_diff_density_rms         0.126
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOH'
####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 1409613'
_audit_update_record             
;
2015-06-30 deposited with the CCDC.
2015-08-10 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT434_3a                  
;
PROBLEM: Short Inter HL..HL Contact I1     ..  I2      ..       3.37 Ang.  
RESPONSE: The short contact indicates interaction between I1 and I2.
;
_vrf_PLAT971_3a                  
;
PROBLEM: Check Calcd Residual Density  0.53A From      I1       2.68 eA-3  
RESPONSE: The large density fluctuations close to iodine are due to the high resolution (theta_max: 52.100) of the data set; tentative truncation of the intensity data to standard resolution resulted in unexceptionally low residual density.
;
# end Validation Reply Form


_audit_creation_date             2015-04-10
_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         'C10 H11 N4 O2 S, 2(I)'
_chemical_formula_sum            'C10 H11 I2 N4 O2 S'
_chemical_formula_weight         505.65
_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                   5.7879(14)
_cell_length_b                   11.983(3)
_cell_length_c                   12.568(3)
_cell_angle_alpha                61.725(3)
_cell_angle_beta                 87.456(2)
_cell_angle_gamma                76.227(2)
_cell_volume                     743.2(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3468
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      39.94
_cell_measurement_theta_min      22.43
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.384
_exptl_absorpt_correction_T_max  0.8799
_exptl_absorpt_correction_T_min  0.7210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    2.260
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             474
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            58775
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         52.100
_diffrn_reflns_theta_min         1.966
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'SMART CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                12136
_reflns_number_total             16488
_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         2.654
_refine_diff_density_min         -1.028
_refine_diff_density_rms         0.223
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         16488
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0428
_refine_ls_restrained_S_all      1.028
_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)+(0.0313P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0969
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
C1 C 0.8200(3) 0.90946(15) 0.44366(13) 0.01195(19) Uani 1 1 d . . . . .
C2 C 1.0053(3) 0.80912(17) 0.64342(14) 0.0151(2) Uani 1 1 d . . . . .
H2 H 0.991(6) 0.793(3) 0.723(3) 0.019(8) Uiso 1 1 d . . . . .
C3 C 1.2094(3) 0.75719(19) 0.60662(16) 0.0178(3) Uani 1 1 d . . . . .
H3 H 1.345(6) 0.697(3) 0.665(3) 0.016(7) Uiso 1 1 d . . . . .
C4 C 1.2045(3) 0.78529(19) 0.48513(16) 0.0172(2) Uani 1 1 d . . . . .
H4 H 1.332(6) 0.750(3) 0.462(3) 0.015(7) Uiso 1 1 d . . . . .
C5 C 0.6355(3) 0.92749(15) 0.18538(13) 0.01176(18) Uani 1 1 d . . . . .
C6 C 0.4569(3) 0.86101(17) 0.20598(14) 0.0144(2) Uani 1 1 d . . . . .
H6 H 0.347(6) 0.877(3) 0.247(3) 0.014(7) Uiso 1 1 d . . . . .
C7 C 0.4742(3) 0.77170(17) 0.16266(15) 0.0149(2) Uani 1 1 d . . . . .
H7 H 0.361(6) 0.721(3) 0.177(3) 0.017(7) Uiso 1 1 d . . . . .
C8 C 0.6655(3) 0.75565(15) 0.09616(13) 0.01260(19) Uani 1 1 d . . . . .
C9 C 0.8425(3) 0.82267(17) 0.07382(15) 0.0144(2) Uani 1 1 d . . . . .
H9 H 0.976(6) 0.811(3) 0.027(3) 0.022(8) Uiso 1 1 d . . . . .
C10 C 0.8283(3) 0.90808(17) 0.12087(14) 0.0142(2) Uani 1 1 d . . . . .
H10 H 0.933(7) 0.959(4) 0.099(3) 0.031(10) Uiso 1 1 d . . . . .
N1 N 0.8149(2) 0.88385(14) 0.56189(12) 0.01325(18) Uani 1 1 d . . . . .
H1 H 0.675(6) 0.920(3) 0.582(3) 0.018(7) Uiso 1 1 d . . . . .
N2 N 1.0181(3) 0.86019(16) 0.40422(13) 0.0154(2) Uani 1 1 d . . . . .
N3 N 0.6155(2) 0.98499(14) 0.37481(11) 0.01334(18) Uani 1 1 d . . . . .
N4 N 0.6803(3) 0.66813(15) 0.04408(13) 0.01461(19) Uani 1 1 d . . . . .
H4A H 0.670(6) 0.709(4) -0.031(3) 0.024(8) Uiso 1 1 d . . . . .
H4B H 0.561(6) 0.627(4) 0.065(3) 0.024(8) Uiso 1 1 d . . . . .
H4C H 0.815(6) 0.613(4) 0.063(3) 0.024(8) Uiso 1 1 d . . . . .
O2 O 0.7866(2) 1.11852(14) 0.17621(12) 0.01655(19) Uani 1 1 d . . . . .
O1 O 0.3585(2) 1.12661(13) 0.19276(11) 0.01579(18) Uani 1 1 d . . . . .
S1 S 0.60422(7) 1.04947(4) 0.23023(3) 0.01167(5) Uani 1 1 d . . . . .
I1 I 1.08752(3) 0.49567(2) 0.39747(2) 0.02315(3) Uani 1 1 d . . . . .
I2 I 1.25918(2) 0.47639(2) 0.14582(2) 0.01460(2) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0135(5) 0.0132(5) 0.0103(4) -0.0065(4) 0.0007(3) -0.0034(4)
C2 0.0162(5) 0.0169(6) 0.0125(5) -0.0074(5) -0.0003(4) -0.0035(4)
C3 0.0149(6) 0.0201(7) 0.0161(6) -0.0075(5) -0.0010(4) -0.0021(5)
C4 0.0144(5) 0.0181(6) 0.0165(5) -0.0076(5) 0.0019(4) -0.0012(5)
C5 0.0127(5) 0.0133(5) 0.0113(4) -0.0075(4) 0.0017(3) -0.0032(4)
C6 0.0142(5) 0.0172(6) 0.0155(5) -0.0102(5) 0.0048(4) -0.0060(4)
C7 0.0152(5) 0.0171(6) 0.0168(5) -0.0107(5) 0.0038(4) -0.0062(4)
C8 0.0139(5) 0.0131(5) 0.0127(4) -0.0075(4) 0.0013(4) -0.0035(4)
C9 0.0147(5) 0.0160(6) 0.0166(5) -0.0107(5) 0.0051(4) -0.0052(4)
C10 0.0145(5) 0.0170(6) 0.0155(5) -0.0104(5) 0.0049(4) -0.0062(4)
N1 0.0143(4) 0.0158(5) 0.0109(4) -0.0076(4) 0.0010(3) -0.0032(4)
N2 0.0139(5) 0.0182(5) 0.0142(4) -0.0092(4) 0.0015(4) -0.0013(4)
N3 0.0127(4) 0.0171(5) 0.0112(4) -0.0083(4) 0.0007(3) -0.0020(4)
N4 0.0164(5) 0.0142(5) 0.0153(5) -0.0091(4) 0.0006(4) -0.0027(4)
O2 0.0205(5) 0.0178(5) 0.0164(4) -0.0101(4) 0.0056(4) -0.0099(4)
O1 0.0161(4) 0.0158(5) 0.0140(4) -0.0079(4) -0.0014(3) 0.0007(4)
S1 0.01361(13) 0.01268(13) 0.01007(11) -0.00665(10) 0.00118(9) -0.00296(10)
I1 0.03173(6) 0.02132(5) 0.01847(5) -0.00935(4) 0.00591(4) -0.01118(5)
I2 0.01523(4) 0.01472(4) 0.01546(4) -0.00894(3) 0.00038(3) -0.00253(3)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.3680(18) . ?
C1 N2 1.347(2) . ?
C1 N3 1.3446(19) . ?
C2 H2 0.93(3) . ?
C2 C3 1.368(2) . ?
C2 N1 1.352(2) . ?
C3 H3 0.98(3) . ?
C3 C4 1.399(2) . ?
C4 H4 0.87(3) . ?
C4 N2 1.332(2) . ?
C5 C6 1.394(2) . ?
C5 C10 1.390(2) . ?
C5 S1 1.7699(15) . ?
C6 H6 0.85(3) . ?
C6 C7 1.396(2) . ?
C7 H7 0.95(3) . ?
C7 C8 1.389(2) . ?
C8 C9 1.388(2) . ?
C8 N4 1.462(2) . ?
C9 H9 0.97(3) . ?
C9 C10 1.390(2) . ?
C10 H10 0.90(4) . ?
N1 H1 0.91(3) . ?
N3 S1 1.5998(14) . ?
N4 H4A 0.83(4) . ?
N4 H4B 0.91(4) . ?
N4 H4C 0.85(4) . ?
O2 S1 1.4421(13) . ?
O1 S1 1.4563(13) . ?
I1 I1 2.7662(7) 2_766 ?

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 C1 N1 120.55(14) . . ?
N3 C1 N1 114.48(13) . . ?
N3 C1 N2 124.97(13) . . ?
C3 C2 H2 122(2) . . ?
N1 C2 H2 119(2) . . ?
N1 C2 C3 118.96(14) . . ?
C2 C3 H3 120.7(19) . . ?
C2 C3 C4 116.68(15) . . ?
C4 C3 H3 122.3(19) . . ?
C3 C4 H4 117(2) . . ?
N2 C4 C3 124.49(16) . . ?
N2 C4 H4 118(2) . . ?
C6 C5 S1 119.59(11) . . ?
C10 C5 C6 121.25(14) . . ?
C10 C5 S1 118.92(12) . . ?
C5 C6 H6 116(2) . . ?
C5 C6 C7 119.34(14) . . ?
C7 C6 H6 125(2) . . ?
C6 C7 H7 123.0(19) . . ?
C8 C7 C6 118.58(14) . . ?
C8 C7 H7 118.4(19) . . ?
C7 C8 N4 119.59(14) . . ?
C9 C8 C7 122.47(14) . . ?
C9 C8 N4 117.91(13) . . ?
C8 C9 H9 122(2) . . ?
C8 C9 C10 118.57(14) . . ?
C10 C9 H9 119(2) . . ?
C5 C10 C9 119.73(14) . . ?
C5 C10 H10 121(2) . . ?
C9 C10 H10 119(2) . . ?
C1 N1 H1 116(2) . . ?
C2 N1 C1 122.10(14) . . ?
C2 N1 H1 122(2) . . ?
C4 N2 C1 117.22(14) . . ?
C1 N3 S1 121.36(11) . . ?
C8 N4 H4A 111(2) . . ?
C8 N4 H4B 112(2) . . ?
C8 N4 H4C 112(2) . . ?
H4A N4 H4B 106(3) . . ?
H4A N4 H4C 104(3) . . ?
H4B N4 H4C 110(3) . . ?
N3 S1 C5 110.21(7) . . ?
O2 S1 C5 107.09(8) . . ?
O2 S1 N3 114.09(8) . . ?
O2 S1 O1 116.16(9) . . ?
O1 S1 C5 105.69(7) . . ?
O1 S1 N3 103.28(7) . . ?

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
N1 H1 N3 0.91(3) 2.00(3) 2.908(2) 174(3) 2_676
N4 H4A O1 0.83(4) 2.03(4) 2.796(2) 154(3) 2_675
N4 H4B I2 0.91(4) 2.63(4) 3.5302(16) 172(3) 1_455
N4 H4C I2 0.85(4) 2.65(4) 3.4742(16) 165(3) .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N3 S1 C5 70.20(15) . . . . ?
C1 N3 S1 O2 -50.29(16) . . . . ?
C1 N3 S1 O1 -177.29(13) . . . . ?
C2 C3 C4 N2 1.3(3) . . . . ?
C3 C2 N1 C1 -0.2(3) . . . . ?
C3 C4 N2 C1 -1.5(3) . . . . ?
C5 C6 C7 C8 -2.4(2) . . . . ?
C6 C5 C10 C9 1.2(2) . . . . ?
C6 C5 S1 N3 66.92(14) . . . . ?
C6 C5 S1 O2 -168.47(13) . . . . ?
C6 C5 S1 O1 -44.03(15) . . . . ?
C6 C7 C8 C9 1.6(3) . . . . ?
C6 C7 C8 N4 -176.60(15) . . . . ?
C7 C8 C9 C10 0.6(3) . . . . ?
C8 C9 C10 C5 -2.0(2) . . . . ?
C10 C5 C6 C7 1.0(2) . . . . ?
C10 C5 S1 N3 -118.58(13) . . . . ?
C10 C5 S1 O2 6.04(15) . . . . ?
C10 C5 S1 O1 130.47(13) . . . . ?
N1 C1 N2 C4 0.8(2) . . . . ?
N1 C1 N3 S1 167.09(12) . . . . ?
N1 C2 C3 C4 -0.5(3) . . . . ?
N2 C1 N1 C2 0.0(2) . . . . ?
N2 C1 N3 S1 -13.2(2) . . . . ?
N3 C1 N1 C2 179.77(15) . . . . ?
N3 C1 N2 C4 -178.96(17) . . . . ?
N4 C8 C9 C10 178.83(15) . . . . ?
S1 C5 C6 C7 175.41(13) . . . . ?
S1 C5 C10 C9 -173.22(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
####################################################################### 
# 
# 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_3b
_database_code_depnum_ccdc_archive 'CCDC 1409614'
_audit_update_record             
;
2015-06-30 deposited with the CCDC.
2015-08-10 downloaded from the CCDC.
;
_audit_creation_date             2015-04-10
_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         'I3, C10 H11 N4 O2 S, C2 H6 O2'
_chemical_formula_sum            'C12 H17 I3 N4 O4 S'
_chemical_formula_weight         694.05
_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                   8.0577(9)
_cell_length_b                   10.8694(12)
_cell_length_c                   11.7471(13)
_cell_angle_alpha                84.291(2)
_cell_angle_beta                 74.230(2)
_cell_angle_gamma                85.792(2)
_cell_volume                     984.05(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2167
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.82
_cell_measurement_theta_min      2.63
_shelx_estimated_absorpt_T_max   0.908
_shelx_estimated_absorpt_T_min   0.374
_exptl_absorpt_coefficient_mu    4.894
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4316
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1334 before and 0.0585 after correction.
The Ratio of minimum to maximum transmission is 0.5785.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.342
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14607
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.672
_diffrn_reflns_theta_min         2.502
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_device_type  'SMART CCD area detector'
_diffrn_measurement_method       'φ and 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                4921
_reflns_number_total             5581
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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         1.466
_refine_diff_density_min         -0.971
_refine_diff_density_rms         0.155
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         5581
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0312
_refine_ls_restrained_S_all      1.025
_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)+(0.0233P)²+0.6523P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0788
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O4-H4D = O3-H3A
 0.9 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10)
;
_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 0.37874(2) 0.66162(2) 0.37869(2) 0.01899(6) Uani 1 1 d . . . . .
I2 I 0.32311(3) 0.49592(2) 0.20208(2) 0.02279(7) Uani 1 1 d . . . . .
I3 I 0.41079(3) 0.82932(2) 0.53919(2) 0.03256(7) Uani 1 1 d . . . . .
S4 S 0.12809(9) 1.04045(6) 0.21246(6) 0.01338(13) Uani 1 1 d . . . . .
O1 O 0.1491(3) 1.16989(18) 0.21897(18) 0.0176(4) Uani 1 1 d . . . . .
O2 O 0.0396(3) 1.01369(19) 0.12664(17) 0.0164(4) Uani 1 1 d . . . . .
N1 N -0.0597(3) 0.8373(2) 0.4925(2) 0.0164(5) Uani 1 1 d . . . . .
H1 H -0.058(5) 0.892(3) 0.545(3) 0.020 Uiso 1 1 d R . . . .
N2 N -0.0376(3) 0.7958(2) 0.2963(2) 0.0172(5) Uani 1 1 d . . . . .
N3 N 0.0405(3) 0.9876(2) 0.3455(2) 0.0144(5) Uani 1 1 d . . . . .
N4 N 0.8441(3) 0.8123(3) 0.0814(2) 0.0169(5) Uani 1 1 d . . . . .
H4A H 0.916(6) 0.849(4) 0.016(4) 0.043(13) Uiso 1 1 d . . . . .
H4B H 0.909(5) 0.821(4) 0.127(4) 0.031(11) Uiso 1 1 d . . . . .
H4C H 0.847(4) 0.740(4) 0.066(3) 0.015(9) Uiso 1 1 d . . . . .
C1 C -0.0163(3) 0.8734(3) 0.3736(2) 0.0133(5) Uani 1 1 d . . . . .
C2 C -0.1164(4) 0.7247(3) 0.5353(3) 0.0194(6) Uani 1 1 d . . . . .
H2 H -0.1441 0.7021 0.6183 0.023 Uiso 1 1 calc R . . . .
C3 C -0.1342(4) 0.6423(3) 0.4592(3) 0.0224(6) Uani 1 1 d . . . . .
H3 H -0.1724 0.5614 0.4866 0.027 Uiso 1 1 calc R . . . .
C4 C -0.0935(4) 0.6835(3) 0.3398(3) 0.0211(6) Uani 1 1 d . . . . .
H4 H -0.1062 0.6282 0.2854 0.025 Uiso 1 1 calc R . . . .
C5 C 0.3377(3) 0.9685(3) 0.1734(2) 0.0141(5) Uani 1 1 d . . . . .
C6 C 0.4605(4) 1.0093(3) 0.2220(3) 0.0181(6) Uani 1 1 d . . . . .
H6 H 0.4306 1.0724 0.2755 0.022 Uiso 1 1 calc R . . . .
C7 C 0.6271(4) 0.9571(3) 0.1921(3) 0.0176(6) Uani 1 1 d . . . . .
H7 H 0.7130 0.9844 0.2241 0.021 Uiso 1 1 calc R . . . .
C8 C 0.6661(4) 0.8650(3) 0.1152(2) 0.0156(5) Uani 1 1 d . . . . .
C9 C 0.5447(4) 0.8233(3) 0.0663(2) 0.0156(5) Uani 1 1 d . . . . .
H9 H 0.5757 0.7604 0.0127 0.019 Uiso 1 1 calc R . . . .
C10 C 0.3762(4) 0.8747(3) 0.0967(2) 0.0148(5) Uani 1 1 d . . . . .
H10 H 0.2899 0.8462 0.0658 0.018 Uiso 1 1 calc R . . . .
O3 O 0.8532(3) 0.3134(2) 0.0029(2) 0.0289(5) Uani 1 1 d D . . . .
H3A H 0.797(7) 0.377(4) -0.028(5) 0.09(2) Uiso 1 1 d D . . . .
O4 O 0.7711(3) 0.5500(2) 0.1111(2) 0.0296(5) Uani 1 1 d D . . . .
H4D H 0.6573(17) 0.539(4) 0.131(4) 0.044 Uiso 1 1 d DR . . . .
C11 C 0.7870(5) 0.3232(3) 0.1274(3) 0.0271(7) Uani 1 1 d . . . . .
H11A H 0.8314 0.2510 0.1707 0.032 Uiso 1 1 calc R . . . .
H11B H 0.6596 0.3211 0.1490 0.032 Uiso 1 1 calc R . . . .
C12 C 0.8362(5) 0.4398(3) 0.1658(3) 0.0308(8) Uani 1 1 d . . . . .
H12A H 0.7915 0.4399 0.2531 0.037 Uiso 1 1 calc R . . . .
H12B H 0.9637 0.4407 0.1460 0.037 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.01947(11) 0.01924(11) 0.01832(10) 0.00170(8) -0.00565(8) -0.00342(8)
I2 0.02334(11) 0.02196(11) 0.02384(11) -0.00192(8) -0.00672(8) -0.00429(8)
I3 0.03394(14) 0.03805(14) 0.03058(13) -0.01381(10) -0.01337(10) -0.00023(10)
S4 0.0130(3) 0.0147(3) 0.0124(3) 0.0002(2) -0.0038(2) -0.0007(2)
O1 0.0194(10) 0.0126(9) 0.0205(10) 0.0008(8) -0.0051(8) -0.0031(8)
O2 0.0164(10) 0.0209(10) 0.0132(9) -0.0002(8) -0.0064(8) -0.0023(8)
N1 0.0208(12) 0.0153(12) 0.0128(11) -0.0012(9) -0.0038(9) -0.0018(10)
N2 0.0190(12) 0.0159(12) 0.0176(12) -0.0025(9) -0.0063(10) -0.0010(9)
N3 0.0153(11) 0.0149(11) 0.0122(11) -0.0010(9) -0.0019(9) -0.0020(9)
N4 0.0149(12) 0.0182(13) 0.0179(12) -0.0029(10) -0.0048(10) 0.0021(10)
C1 0.0125(12) 0.0140(12) 0.0126(12) -0.0006(10) -0.0026(10) 0.0001(10)
C2 0.0250(15) 0.0156(14) 0.0158(13) 0.0015(11) -0.0020(11) -0.0048(12)
C3 0.0274(16) 0.0153(14) 0.0235(15) -0.0001(12) -0.0038(13) -0.0066(12)
C4 0.0255(16) 0.0189(14) 0.0219(15) -0.0017(12) -0.0108(13) -0.0041(12)
C5 0.0120(12) 0.0156(13) 0.0139(12) 0.0020(10) -0.0026(10) -0.0022(10)
C6 0.0158(13) 0.0225(15) 0.0166(13) -0.0058(11) -0.0039(11) -0.0012(11)
C7 0.0170(14) 0.0219(14) 0.0155(13) -0.0018(11) -0.0064(11) -0.0039(11)
C8 0.0147(13) 0.0159(13) 0.0155(13) 0.0022(10) -0.0044(10) 0.0009(10)
C9 0.0189(14) 0.0142(13) 0.0138(13) -0.0021(10) -0.0046(11) 0.0007(11)
C10 0.0137(13) 0.0176(13) 0.0135(12) -0.0015(10) -0.0038(10) -0.0019(10)
O3 0.0288(13) 0.0273(13) 0.0322(13) -0.0099(10) -0.0100(11) 0.0061(10)
O4 0.0230(12) 0.0215(12) 0.0430(15) -0.0073(10) -0.0050(11) -0.0015(10)
C11 0.0267(17) 0.0210(16) 0.0349(18) -0.0079(14) -0.0098(14) 0.0031(13)
C12 0.0333(19) 0.0261(17) 0.038(2) -0.0111(15) -0.0164(16) 0.0018(15)

_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 I2 3.0193(4) . ?
I1 I3 2.8217(4) . ?
S4 O1 1.441(2) . ?
S4 O2 1.445(2) . ?
S4 N3 1.598(2) . ?
S4 C5 1.769(3) . ?
N1 H1 0.90(4) . ?
N1 C1 1.369(4) . ?
N1 C2 1.340(4) . ?
N2 C1 1.350(4) . ?
N2 C4 1.336(4) . ?
N3 C1 1.334(4) . ?
N4 H4A 0.90(5) . ?
N4 H4B 0.86(4) . ?
N4 H4C 0.82(4) . ?
N4 C8 1.469(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.367(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(4) . ?
C5 C10 1.390(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.385(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.377(4) . ?
C8 C9 1.384(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.395(4) . ?
C10 H10 0.9500 . ?
O3 H3A 0.900(10) . ?
O3 C11 1.426(4) . ?
O4 H4D 0.897(10) . ?
O4 C12 1.436(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.501(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?

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
I3 I1 I2 175.548(9) . . ?
O1 S4 O2 115.27(12) . . ?
O1 S4 N3 105.53(13) . . ?
O1 S4 C5 106.88(13) . . ?
O2 S4 N3 114.49(13) . . ?
O2 S4 C5 108.01(13) . . ?
N3 S4 C5 106.05(13) . . ?
C1 N1 H1 120(2) . . ?
C2 N1 H1 118(2) . . ?
C2 N1 C1 122.1(3) . . ?
C4 N2 C1 117.7(3) . . ?
C1 N3 S4 123.1(2) . . ?
H4A N4 H4B 94(4) . . ?
H4A N4 H4C 104(4) . . ?
H4B N4 H4C 111(4) . . ?
C8 N4 H4A 117(3) . . ?
C8 N4 H4B 118(3) . . ?
C8 N4 H4C 111(2) . . ?
N2 C1 N1 119.6(3) . . ?
N3 C1 N1 114.6(2) . . ?
N3 C1 N2 125.7(3) . . ?
N1 C2 H2 120.1 . . ?
N1 C2 C3 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 121.8 . . ?
C2 C3 C4 116.3(3) . . ?
C4 C3 H3 121.8 . . ?
N2 C4 C3 124.4(3) . . ?
N2 C4 H4 117.8 . . ?
C3 C4 H4 117.8 . . ?
C6 C5 S4 117.5(2) . . ?
C6 C5 C10 121.8(3) . . ?
C10 C5 S4 120.7(2) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 C5 119.4(3) . . ?
C7 C6 H6 120.3 . . ?
C6 C7 H7 120.6 . . ?
C8 C7 C6 118.9(3) . . ?
C8 C7 H7 120.6 . . ?
C7 C8 N4 118.6(3) . . ?
C7 C8 C9 122.2(3) . . ?
C9 C8 N4 119.1(3) . . ?
C8 C9 H9 120.4 . . ?
C8 C9 C10 119.3(3) . . ?
C10 C9 H9 120.4 . . ?
C5 C10 C9 118.4(3) . . ?
C5 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
C11 O3 H3A 103(4) . . ?
C12 O4 H4D 102(3) . . ?
O3 C11 H11A 109.1 . . ?
O3 C11 H11B 109.1 . . ?
O3 C11 C12 112.5(3) . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
O4 C12 C11 113.1(3) . . ?
O4 C12 H12A 109.0 . . ?
O4 C12 H12B 109.0 . . ?
C11 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?

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
N1 H1 N3 0.90(4) 1.96(4) 2.862(3) 177(3) 2_576
N4 H4A O2 0.90(5) 2.10(5) 2.919(3) 150(4) 2_675
N4 H4B N2 0.86(4) 2.13(4) 2.916(4) 151(4) 1_655

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
S4 N3 C1 N1 169.2(2) . . . . ?
S4 N3 C1 N2 -12.7(4) . . . . ?
S4 C5 C6 C7 -178.8(2) . . . . ?
S4 C5 C10 C9 178.3(2) . . . . ?
O1 S4 N3 C1 172.6(2) . . . . ?
O1 S4 C5 C6 37.8(3) . . . . ?
O1 S4 C5 C10 -142.3(2) . . . . ?
O2 S4 N3 C1 44.7(3) . . . . ?
O2 S4 C5 C6 162.4(2) . . . . ?
O2 S4 C5 C10 -17.7(3) . . . . ?
N1 C2 C3 C4 -1.0(5) . . . . ?
N3 S4 C5 C6 -74.5(3) . . . . ?
N3 S4 C5 C10 105.5(2) . . . . ?
N4 C8 C9 C10 -178.9(3) . . . . ?
C1 N1 C2 C3 -0.8(5) . . . . ?
C1 N2 C4 C3 1.3(5) . . . . ?
C2 N1 C1 N2 2.9(4) . . . . ?
C2 N1 C1 N3 -178.9(3) . . . . ?
C2 C3 C4 N2 0.7(5) . . . . ?
C4 N2 C1 N1 -3.0(4) . . . . ?
C4 N2 C1 N3 179.0(3) . . . . ?
C5 S4 N3 C1 -74.2(3) . . . . ?
C5 C6 C7 C8 -0.5(4) . . . . ?
C6 C5 C10 C9 -1.7(4) . . . . ?
C6 C7 C8 N4 178.5(3) . . . . ?
C6 C7 C8 C9 0.4(5) . . . . ?
C7 C8 C9 C10 -0.9(4) . . . . ?
C8 C9 C10 C5 1.5(4) . . . . ?
C10 C5 C6 C7 1.3(4) . . . . ?
O3 C11 C12 O4 61.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeOH and Ethylene glycol'
####################################################################### 
# 
# 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_3c
_database_code_depnum_ccdc_archive 'CCDC 1409615'
_audit_update_record             
;
2015-06-30 deposited with the CCDC.
2015-08-10 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT434_3c                  
;
PROBLEM: Short Inter HL..HL Contact I3 .. I4 .. 3.22 Ang.
RESPONSE: The short interatomic distance indicates the
interaction between the two iodine atoms.
;
_vrf_PLAT971_3c                  
;
PROBLEM: Check Calcd Residual Density 0.86A From I1 3.12 eA-3
RESPONSE: The relatively large residual density is close to
heavy halogen atom, which might be caused by the electronic
polarization of the corresponding halogen atom, or unsuitable
absorption correction.
;
# end Validation Reply Form

_audit_creation_date             2015-04-10
_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         '1.67(I3), C10 H11 N4 O2 S'
_chemical_formula_sum            'C10 H11 I5 N4 O2 S'
_chemical_formula_weight         885.79
_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                   8.004(2)
_cell_length_b                   11.247(3)
_cell_length_c                   11.473(3)
_cell_angle_alpha                83.925(4)
_cell_angle_beta                 89.442(4)
_cell_angle_gamma                72.371(4)
_cell_volume                     978.6(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3982
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.07
_cell_measurement_theta_min      2.47
_shelx_estimated_absorpt_T_max   0.739
_shelx_estimated_absorpt_T_min   0.189
_exptl_absorpt_coefficient_mu    8.062
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.4903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1443 before and 0.0657 after correction.
The Ratio of minimum to maximum transmission is 0.6572.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    3.006
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13904
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.338
_diffrn_reflns_theta_min         1.911
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device_type  'SMART CCD area detector'
_diffrn_measurement_method       'φ and 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                4298
_reflns_number_total             5420
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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         2.942
_refine_diff_density_min         -1.406
_refine_diff_density_rms         0.299
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         5420
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0475
_refine_ls_restrained_S_all      1.070
_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)+(0.0470P)²+4.6929P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1252
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N4-H4B
 0.9 with sigma of 0.02
 N4-H4C
 0.9 with sigma of 0.02
 N4-H4A
 0.9 with sigma of 0.02
 H1-N1
 0.95 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10)
;
_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 0.10015(7) 0.50727(5) 0.35561(5) 0.02526(13) Uani 1 1 d . . . . .
I2 I 0.18374(6) 0.64391(5) 0.15247(4) 0.02192(13) Uani 1 1 d . . . . .
I3 I 0.31625(7) 0.78035(5) -0.05187(5) 0.02510(13) Uani 1 1 d . . . . .
I5 I 0.18239(7) 1.25172(5) 0.18036(5) 0.03062(15) Uani 1 1 d . . . . .
I4 I 0.24430(7) 1.04113(5) 0.06065(5) 0.02611(14) Uani 1 1 d . . . . .
S1 S 0.3644(2) 0.79035(16) 0.51750(15) 0.0150(3) Uani 1 1 d . . . . .
O1 O 0.3433(6) 0.7612(5) 0.6416(5) 0.0190(10) Uani 1 1 d . . . . .
O2 O 0.4465(6) 0.8880(5) 0.4873(5) 0.0190(10) Uani 1 1 d . . . . .
N1 N 0.5901(8) 0.5237(6) 0.3400(5) 0.0169(12) Uani 1 1 d D . . . .
H1 H 0.577(14) 0.474(8) 0.410(5) 0.05(3) Uiso 1 1 d D . . . .
N2 N 0.5642(8) 0.7370(6) 0.2888(6) 0.0186(12) Uani 1 1 d . . . . .
N3 N 0.4618(7) 0.6597(6) 0.4710(5) 0.0170(12) Uani 1 1 d . . . . .
N4 N -0.3626(8) 0.9705(6) 0.3111(6) 0.0185(12) Uani 1 1 d D . . . .
H4A H -0.420(10) 1.017(7) 0.367(5) 0.02(2) Uiso 1 1 d D . . . .
H4B H -0.401(15) 0.907(8) 0.292(11) 0.06(4) Uiso 1 1 d D . . . .
H4C H -0.365(12) 1.025(7) 0.248(5) 0.03(2) Uiso 1 1 d D . . . .
C1 C 0.5376(9) 0.6446(7) 0.3658(6) 0.0169(14) Uani 1 1 d . . . . .
C2 C 0.6657(9) 0.4916(7) 0.2379(7) 0.0210(15) Uani 1 1 d . . . . .
H2 H 0.7016 0.4063 0.2225 0.025 Uiso 1 1 calc R . . . .
C3 C 0.6905(10) 0.5814(8) 0.1570(7) 0.0247(16) Uani 1 1 d . . . . .
H3 H 0.7419 0.5618 0.0838 0.030 Uiso 1 1 calc R . . . .
C4 C 0.6370(9) 0.7032(7) 0.1869(7) 0.0202(15) Uani 1 1 d . . . . .
H4 H 0.6530 0.7674 0.1312 0.024 Uiso 1 1 calc R . . . .
C5 C 0.1532(8) 0.8417(6) 0.4527(6) 0.0163(14) Uani 1 1 d . . . . .
C6 C 0.0243(10) 0.7961(7) 0.5038(7) 0.0249(17) Uani 1 1 d . . . . .
H6 H 0.0509 0.7376 0.5721 0.030 Uiso 1 1 calc R . . . .
C7 C -0.1431(10) 0.8361(7) 0.4550(7) 0.0230(16) Uani 1 1 d . . . . .
H7 H -0.2317 0.8038 0.4885 0.028 Uiso 1 1 calc R . . . .
C8 C -0.1804(9) 0.9224(7) 0.3580(7) 0.0173(14) Uani 1 1 d . . . . .
C9 C -0.0543(10) 0.9682(8) 0.3047(7) 0.0257(17) Uani 1 1 d . . . . .
H9 H -0.0821 1.0256 0.2356 0.031 Uiso 1 1 calc R . . . .
C10 C 0.1165(10) 0.9288(8) 0.3541(7) 0.0252(17) Uani 1 1 d . . . . .
H10 H 0.2049 0.9613 0.3207 0.030 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.0231(3) 0.0277(3) 0.0266(3) -0.0010(2) 0.00150(19) -0.0109(2)
I2 0.0192(2) 0.0213(2) 0.0258(3) -0.00256(19) -0.00101(18) -0.00701(18)
I3 0.0278(3) 0.0246(3) 0.0221(3) 0.00036(19) -0.00019(19) -0.0077(2)
I5 0.0301(3) 0.0295(3) 0.0350(3) -0.0017(2) 0.0060(2) -0.0139(2)
I4 0.0231(3) 0.0280(3) 0.0264(3) 0.0031(2) 0.00463(19) -0.0088(2)
S1 0.0109(7) 0.0123(8) 0.0213(9) -0.0011(6) 0.0005(6) -0.0030(6)
O1 0.017(2) 0.018(3) 0.023(3) -0.005(2) -0.0002(19) -0.0049(19)
O2 0.017(2) 0.015(2) 0.029(3) -0.003(2) 0.002(2) -0.0099(19)
N1 0.018(3) 0.017(3) 0.017(3) 0.001(2) 0.000(2) -0.006(2)
N2 0.020(3) 0.016(3) 0.022(3) -0.003(2) 0.002(2) -0.008(2)
N3 0.013(3) 0.018(3) 0.021(3) -0.001(2) -0.001(2) -0.006(2)
N4 0.014(3) 0.016(3) 0.026(3) -0.001(2) 0.003(2) -0.007(2)
C1 0.015(3) 0.015(3) 0.023(4) -0.003(3) 0.000(3) -0.010(3)
C2 0.018(3) 0.019(4) 0.029(4) -0.006(3) 0.006(3) -0.008(3)
C3 0.023(4) 0.029(4) 0.021(4) -0.004(3) 0.006(3) -0.006(3)
C4 0.019(3) 0.022(4) 0.019(4) 0.007(3) -0.002(3) -0.007(3)
C5 0.009(3) 0.014(3) 0.026(4) -0.001(3) 0.001(2) -0.004(2)
C6 0.021(4) 0.021(4) 0.029(4) 0.013(3) -0.001(3) -0.006(3)
C7 0.021(4) 0.019(4) 0.030(4) 0.004(3) 0.000(3) -0.010(3)
C8 0.011(3) 0.014(3) 0.027(4) -0.003(3) 0.000(3) -0.003(2)
C9 0.020(4) 0.028(4) 0.030(4) 0.007(3) 0.000(3) -0.011(3)
C10 0.016(3) 0.030(4) 0.031(4) 0.000(3) 0.009(3) -0.011(3)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 I2 2.8419(9) . ?
I2 I3 3.0252(9) . ?
I5 I4 2.7761(10) . ?
S1 O1 1.447(5) . ?
S1 O2 1.453(5) . ?
S1 N3 1.586(6) . ?
S1 C5 1.757(7) . ?
N1 H1 0.95(2) . ?
N1 C1 1.361(9) . ?
N1 C2 1.346(9) . ?
N2 C1 1.357(9) . ?
N2 C4 1.341(9) . ?
N3 C1 1.349(9) . ?
N4 H4A 0.90(2) . ?
N4 H4B 0.90(2) . ?
N4 H4C 0.90(2) . ?
N4 C8 1.478(9) . ?
C2 H2 0.9500 . ?
C2 C3 1.356(11) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(11) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(10) . ?
C5 C10 1.387(11) . ?
C6 H6 0.9500 . ?
C6 C7 1.381(11) . ?
C7 H7 0.9500 . ?
C7 C8 1.368(10) . ?
C8 C9 1.377(10) . ?
C9 H9 0.9500 . ?
C9 C10 1.408(11) . ?
C10 H10 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
I1 I2 I3 173.25(2) . . ?
O1 S1 O2 115.3(3) . . ?
O1 S1 N3 105.2(3) . . ?
O1 S1 C5 106.8(3) . . ?
O2 S1 N3 114.7(3) . . ?
O2 S1 C5 107.6(3) . . ?
N3 S1 C5 106.6(3) . . ?
C1 N1 H1 106(7) . . ?
C2 N1 H1 132(6) . . ?
C2 N1 C1 122.0(6) . . ?
C4 N2 C1 116.9(6) . . ?
C1 N3 S1 125.5(5) . . ?
H4A N4 H4B 118(10) . . ?
H4A N4 H4C 106(8) . . ?
H4B N4 H4C 111(10) . . ?
C8 N4 H4A 103(5) . . ?
C8 N4 H4B 111(8) . . ?
C8 N4 H4C 108(6) . . ?
N2 C1 N1 120.1(6) . . ?
N3 C1 N1 113.9(6) . . ?
N3 C1 N2 125.9(6) . . ?
N1 C2 H2 120.1 . . ?
N1 C2 C3 119.9(7) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 121.7 . . ?
C2 C3 C4 116.5(7) . . ?
C4 C3 H3 121.7 . . ?
N2 C4 C3 124.6(7) . . ?
N2 C4 H4 117.7 . . ?
C3 C4 H4 117.7 . . ?
C6 C5 S1 118.7(6) . . ?
C6 C5 C10 121.1(7) . . ?
C10 C5 S1 120.2(5) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.7(7) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.5(7) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 N4 119.0(6) . . ?
C7 C8 C9 122.0(7) . . ?
C9 C8 N4 119.0(7) . . ?
C8 C9 H9 120.5 . . ?
C8 C9 C10 119.0(7) . . ?
C10 C9 H9 120.5 . . ?
C5 C10 C9 118.7(7) . . ?
C5 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?

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
N1 H1 N3 0.95(2) 2.02(4) 2.946(8) 165(10) 2_666
N4 H4A O2 0.90(2) 2.05(4) 2.904(9) 156(8) 2_576
N4 H4B N2 0.90(2) 2.02(4) 2.895(9) 163(11) 1_455

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 N3 C1 N1 -171.0(5) . . . . ?
S1 N3 C1 N2 9.4(11) . . . . ?
S1 C5 C6 C7 179.4(6) . . . . ?
S1 C5 C10 C9 -179.8(6) . . . . ?
O1 S1 N3 C1 -166.6(6) . . . . ?
O1 S1 C5 C6 -29.0(7) . . . . ?
O1 S1 C5 C10 149.2(6) . . . . ?
O2 S1 N3 C1 -38.8(7) . . . . ?
O2 S1 C5 C6 -153.4(6) . . . . ?
O2 S1 C5 C10 24.8(7) . . . . ?
N1 C2 C3 C4 1.0(11) . . . . ?
N3 S1 C5 C6 83.1(7) . . . . ?
N3 S1 C5 C10 -98.7(7) . . . . ?
N4 C8 C9 C10 175.7(7) . . . . ?
C1 N1 C2 C3 -0.3(11) . . . . ?
C1 N2 C4 C3 -1.9(11) . . . . ?
C2 N1 C1 N2 -1.5(11) . . . . ?
C2 N1 C1 N3 178.9(7) . . . . ?
C2 C3 C4 N2 0.2(12) . . . . ?
C4 N2 C1 N1 2.5(10) . . . . ?
C4 N2 C1 N3 -178.0(7) . . . . ?
C5 S1 N3 C1 80.2(7) . . . . ?
C5 C6 C7 C8 -1.4(12) . . . . ?
C6 C5 C10 C9 -1.6(12) . . . . ?
C6 C7 C8 N4 -176.1(7) . . . . ?
C6 C7 C8 C9 2.1(12) . . . . ?
C7 C8 C9 C10 -2.5(13) . . . . ?
C8 C9 C10 C5 2.2(12) . . . . ?
C10 C5 C6 C7 1.2(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOH'
