# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

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

data_2_IODO
_database_code_depnum_ccdc_archive 'CCDC 1046367'
_audit_update_record             
;
2016-07-21 deposited with the CCDC.
2016-08-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H7 I N2 O'
_chemical_formula_sum            'C7 H7 I N2 O'
_chemical_formula_weight         262.05

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.8183(6)
_cell_length_b                   7.9251(4)
_cell_length_c                   8.9570(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.047(3)
_cell_angle_gamma                90
_cell_volume                     838.92(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5909
_cell_measurement_theta_min      3.84
_cell_measurement_theta_max      34.62

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.075
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.320
_exptl_absorpt_coefficient_mu    3.760
_shelx_estimated_absorpt_T_min   0.282
_shelx_estimated_absorpt_T_max   0.379
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.282
_exptl_absorpt_correction_T_max  0.379
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13070
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.842
_diffrn_reflns_theta_max         34.778
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3612
_reflns_number_gt                2975
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0396P)²+0.4754P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3612
_refine_ls_number_parameters     112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0952
_refine_ls_wR_factor_gt          0.0899
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_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_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 0.39038(2) 0.17150(2) -0.04891(2) 0.04647(8) Uani 1 1 d . . . . .
O1 O 0.09066(16) 0.1754(2) -0.06404(16) 0.0369(4) Uani 1 1 d . . . . .
N1 N 0.17022(18) 0.3213(3) 0.1281(2) 0.0352(4) Uani 1 1 d . . . . .
N2 N 0.0683(2) 0.0819(3) 0.1733(2) 0.0415(5) Uani 1 1 d . . . . .
C1 C 0.10825(16) 0.1911(3) 0.0724(2) 0.0286(4) Uani 1 1 d . . . . .
C2 C 0.21973(18) 0.4448(3) 0.0346(2) 0.0304(4) Uani 1 1 d . . . . .
C3 C 0.31501(18) 0.4103(3) -0.0518(2) 0.0301(4) Uani 1 1 d . . . . .
C4 C 0.3626(2) 0.5345(4) -0.1412(3) 0.0426(5) Uani 1 1 d . . . . .
H4 H 0.4267 0.5108 -0.1976 0.051 Uiso 1 1 calc R U . . .
C5 C 0.3147(3) 0.6933(4) -0.1463(4) 0.0511(7) Uani 1 1 d . . . . .
H5 H 0.3454 0.7757 -0.2081 0.061 Uiso 1 1 calc R U . . .
C6 C 0.2217(3) 0.7299(4) -0.0601(4) 0.0529(7) Uani 1 1 d . . . . .
H6 H 0.1911 0.8380 -0.0616 0.063 Uiso 1 1 calc R U . . .
C7 C 0.1735(2) 0.6066(4) 0.0289(3) 0.0440(5) Uani 1 1 d . . . . .
H7 H 0.1097 0.6319 0.0854 0.053 Uiso 1 1 calc R U . . .
H1 H 0.169(4) 0.345(4) 0.227(5) 0.057(11) Uiso 1 1 d . . . . .
H2A H 0.078(3) 0.101(5) 0.267(4) 0.049(9) Uiso 1 1 d . . . . .
H2B H 0.034(3) 0.005(4) 0.148(4) 0.041(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C3 2.092(2) . ?
O1 C1 1.246(2) . ?
N1 C1 1.360(3) . ?
N1 C2 1.415(3) . ?
N1 H1 0.90(4) . ?
N2 C1 1.337(3) . ?
N2 H2A 0.86(4) . ?
N2 H2B 0.77(4) . ?
C2 C3 1.394(3) . ?
C2 C7 1.395(4) . ?
C3 C4 1.389(3) . ?
C4 C5 1.381(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.384(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?

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
C1 N1 C2 122.05(17) . . ?
C1 N1 H1 120(2) . . ?
C2 N1 H1 116(2) . . ?
C1 N2 H2A 120(3) . . ?
C1 N2 H2B 120(3) . . ?
H2A N2 H2B 120(4) . . ?
O1 C1 N2 122.6(2) . . ?
O1 C1 N1 121.67(19) . . ?
N2 C1 N1 115.70(18) . . ?
C3 C2 C7 118.5(2) . . ?
C3 C2 N1 121.8(2) . . ?
C7 C2 N1 119.7(2) . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 I1 118.41(17) . . ?
C2 C3 I1 120.99(16) . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 120.3(3) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C6 C7 C2 120.5(2) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?

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
C2 N1 C1 O1 -1.0(4) . . . . ?
C2 N1 C1 N2 178.7(2) . . . . ?
C1 N1 C2 C3 -74.1(3) . . . . ?
C1 N1 C2 C7 106.6(3) . . . . ?
C7 C2 C3 C4 0.1(3) . . . . ?
N1 C2 C3 C4 -179.2(2) . . . . ?
C7 C2 C3 I1 179.60(17) . . . . ?
N1 C2 C3 I1 0.3(3) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
I1 C3 C4 C5 179.7(2) . . . . ?
C3 C4 C5 C6 1.7(5) . . . . ?
C4 C5 C6 C7 -1.9(5) . . . . ?
C5 C6 C7 C2 1.2(5) . . . . ?
C3 C2 C7 C6 -0.3(4) . . . . ?
N1 C2 C7 C6 179.0(2) . . . . ?

_refine_diff_density_max         1.392
_refine_diff_density_min         -0.987
_refine_diff_density_rms         0.124

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_ABC
_database_code_depnum_ccdc_archive 'CCDC 1046368'
_audit_update_record             
;
2016-07-21 deposited with the CCDC.
2016-08-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H7 I N2 O'
_chemical_formula_sum            'C7 H7 I N2 O'
_chemical_formula_weight         262.05

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y+1/2, z'
'-x, -y, -z'
'-x-1/2, y, z-1/2'
'x, -y-1/2, z-1/2'
'x-1/2, y-1/2, -z'

_cell_length_a                   21.4515(4)
_cell_length_b                   8.44460(10)
_cell_length_c                   8.99770(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1629.93(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9864
_cell_measurement_theta_min      3.44
_cell_measurement_theta_max      36.81

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.136
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    3.871
_shelx_estimated_absorpt_T_min   0.275
_shelx_estimated_absorpt_T_max   0.390
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.275
_exptl_absorpt_correction_T_max  0.390
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            57286
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.442
_diffrn_reflns_theta_max         43.946
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5815
_reflns_number_gt                4231
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0820P)²+3.6784P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5815
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1520
_refine_ls_wR_factor_gt          0.1360
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_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_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 0.26740(2) 0.01688(3) 0.84309(2) 0.02672(7) Uani 1 1 d . . . . .
O1 O 0.45170(8) 0.3322(2) 0.57505(16) 0.0155(3) Uani 1 1 d . . . . .
N2 N 0.46616(9) 0.4109(3) 0.33627(18) 0.0156(3) Uani 1 1 d . . . . .
H2B H 0.4857 0.4977 0.3638 0.019 Uiso 1 1 calc R U . . .
H2A H 0.4605 0.3908 0.2413 0.019 Uiso 1 1 calc R U . . .
N1 N 0.41563(9) 0.1779(2) 0.38498(18) 0.0145(3) Uani 1 1 d . . . . .
H1 H 0.4117 0.1687 0.2880 0.017 Uiso 1 1 calc R U . . .
C1 C 0.44487(8) 0.3089(3) 0.4395(2) 0.0115(3) Uani 1 1 d . . . . .
C2 C 0.39128(9) 0.0564(3) 0.4757(2) 0.0120(3) Uani 1 1 d . . . . .
C3 C 0.34937(9) 0.0920(2) 0.5897(2) 0.0119(3) Uani 1 1 d . . . . .
H3 H 0.3371 0.1982 0.6084 0.014 Uiso 1 1 calc R U . . .
C4 C 0.32601(10) -0.0324(3) 0.6754(2) 0.0130(3) Uani 1 1 d . . . . .
C5 C 0.34152(11) -0.1885(3) 0.6476(2) 0.0162(3) Uani 1 1 d . . . . .
H5 H 0.3244 -0.2713 0.7063 0.019 Uiso 1 1 calc R U . . .
C6 C 0.38271(11) -0.2223(3) 0.5319(3) 0.0188(4) Uani 1 1 d . . . . .
H6 H 0.3936 -0.3291 0.5109 0.023 Uiso 1 1 calc R U . . .
C7 C 0.40779(10) -0.1012(3) 0.4477(2) 0.0168(3) Uani 1 1 d . . . . .
H7 H 0.4364 -0.1250 0.3703 0.020 Uiso 1 1 calc R U . . .


_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 C4 2.008(2) . ?
O1 C1 1.244(2) . ?
N2 C1 1.347(3) . ?
N2 H2B 0.8800 . ?
N2 H2A 0.8800 . ?
N1 C1 1.363(3) . ?
N1 C2 1.412(3) . ?
N1 H1 0.8800 . ?
C2 C3 1.397(3) . ?
C2 C7 1.400(3) . ?
C3 C4 1.396(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(3) . ?
C5 C6 1.395(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(3) . ?
C6 H6 0.9500 . ?
C7 H7 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
C1 N2 H2B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
H2B N2 H2A 120.0 . . ?
C1 N1 C2 123.52(16) . . ?
C1 N1 H1 118.2 . . ?
C2 N1 H1 118.2 . . ?
O1 C1 N2 122.33(19) . . ?
O1 C1 N1 122.39(18) . . ?
N2 C1 N1 115.28(17) . . ?
C3 C2 C7 120.01(19) . . ?
C3 C2 N1 120.39(19) . . ?
C7 C2 N1 119.57(18) . . ?
C4 C3 C2 118.30(19) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C5 C4 C3 122.11(18) . . ?
C5 C4 I1 118.95(15) . . ?
C3 C4 I1 118.94(15) . . ?
C4 C5 C6 118.8(2) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C7 C6 C5 120.3(2) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C2 120.41(19) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 O1 -0.9(3) . . . . ?
C2 N1 C1 N2 178.8(2) . . . . ?
C1 N1 C2 C3 54.0(3) . . . . ?
C1 N1 C2 C7 -128.1(2) . . . . ?
C7 C2 C3 C4 1.4(3) . . . . ?
N1 C2 C3 C4 179.27(18) . . . . ?
C2 C3 C4 C5 -2.1(3) . . . . ?
C2 C3 C4 I1 178.45(14) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
I1 C4 C5 C6 -179.41(17) . . . . ?
C4 C5 C6 C7 0.5(4) . . . . ?
C5 C6 C7 C2 -1.2(4) . . . . ?
C3 C2 C7 C6 0.2(3) . . . . ?
N1 C2 C7 C6 -177.7(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
N2 H2B O1 0.88 2.04 2.906(2) 167.2 5_666
N2 H2A O1 0.88 2.41 3.136(3) 139.8 7_565
N1 H1 O1 0.88 2.10 2.895(2) 150.0 7_565

_refine_diff_density_max         1.579
_refine_diff_density_min         -2.587
_refine_diff_density_rms         0.236

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_4IODO_LT_0m
_database_code_depnum_ccdc_archive 'CCDC 1046369'
_audit_update_record             
;
2016-07-21 deposited with the CCDC.
2016-08-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H7 I N2 O'
_chemical_formula_sum            'C7 H7 I N2 O'
_chemical_formula_weight         262.05

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   4.6211(7)
_cell_length_b                   5.2775(8)
_cell_length_c                   16.932(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.344(2)
_cell_angle_gamma                90
_cell_volume                     410.40(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5733
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      31.44

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.121
_exptl_crystal_F_000             248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.270
_exptl_absorpt_coefficient_mu    3.843
_shelx_estimated_absorpt_T_min   0.309
_shelx_estimated_absorpt_T_max   0.423
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.309
_exptl_absorpt_correction_T_max  0.423
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6434
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.421
_diffrn_reflns_theta_max         31.586
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2567
_reflns_number_gt                2544
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.779
_reflns_Friedel_fraction_max     0.906
_reflns_Friedel_fraction_full    0.998

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0114P)²+0.0464P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1105 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.020(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2567
_refine_ls_number_parameters     100
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0150
_refine_ls_R_factor_gt           0.0148
_refine_ls_wR_factor_ref         0.0359
_refine_ls_wR_factor_gt          0.0358
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_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_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 0.16022(3) 0.14651(5) 0.07668(2) 0.02560(5) Uani 1 1 d . . . . .
O1 O 0.3716(3) 0.9251(4) 0.41485(10) 0.0182(3) Uani 1 1 d . . . . .
N1 N 0.7733(4) 0.8079(4) 0.35602(13) 0.0198(4) Uani 1 1 d . . . . .
H1 H 0.9643 0.8167 0.3587 0.024 Uiso 1 1 calc R U . . .
N2 N 0.8144(4) 1.0743(4) 0.46320(15) 0.0229(4) Uani 1 1 d . . . . .
H2A H 0.7412 1.1587 0.5012 0.028 Uiso 1 1 calc R U . . .
H2B H 1.0027 1.0799 0.4594 0.028 Uiso 1 1 calc R U . . .
C1 C 0.6393(5) 0.9374(4) 0.41121(14) 0.0157(4) Uani 1 1 d . . . . .
C2 C 0.6247(4) 0.6592(9) 0.29435(11) 0.0177(4) Uani 1 1 d . . . . .
C3 C 0.4267(6) 0.4726(5) 0.30964(15) 0.0225(5) Uani 1 1 d . . . . .
H3 H 0.3819 0.4448 0.3624 0.027 Uiso 1 1 calc R U . . .
C4 C 0.2942(6) 0.3267(5) 0.24750(15) 0.0251(5) Uani 1 1 d . . . . .
H4 H 0.1575 0.1997 0.2577 0.030 Uiso 1 1 calc R U . . .
C5 C 0.3612(5) 0.3661(5) 0.17069(15) 0.0204(4) Uani 1 1 d . . . . .
C6 C 0.5597(6) 0.5512(5) 0.15493(15) 0.0245(5) Uani 1 1 d . . . . .
H6 H 0.6057 0.5773 0.1022 0.029 Uiso 1 1 calc R U . . .
C7 C 0.6906(6) 0.6979(5) 0.21680(16) 0.0258(6) Uani 1 1 d . . . . .
H7 H 0.8260 0.8256 0.2063 0.031 Uiso 1 1 calc R U . . .


_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 C5 2.101(2) . ?
O1 C1 1.247(3) . ?
N1 C1 1.361(3) . ?
N1 C2 1.421(3) . ?
N1 H1 0.8800 . ?
N2 C1 1.340(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
C2 C3 1.388(4) . ?
C2 C7 1.395(3) . ?
C3 C4 1.390(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(4) . ?
C6 C7 1.386(4) . ?
C6 H6 0.9500 . ?
C7 H7 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
C1 N1 C2 124.23(19) . . ?
C1 N1 H1 117.9 . . ?
C2 N1 H1 117.9 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
O1 C1 N2 121.7(2) . . ?
O1 C1 N1 122.5(2) . . ?
N2 C1 N1 115.76(19) . . ?
C3 C2 C7 119.7(3) . . ?
C3 C2 N1 122.0(2) . . ?
C7 C2 N1 118.2(3) . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 I1 120.17(18) . . ?
C6 C5 I1 119.31(19) . . ?
C5 C6 C7 119.4(2) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C6 C7 C2 120.5(2) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 O1 4.0(4) . . . . ?
C2 N1 C1 N2 -177.8(3) . . . . ?
C1 N1 C2 C3 -52.3(4) . . . . ?
C1 N1 C2 C7 130.2(3) . . . . ?
C7 C2 C3 C4 -0.4(4) . . . . ?
N1 C2 C3 C4 -177.9(3) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C3 C4 C5 I1 -179.8(2) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
I1 C5 C6 C7 179.4(2) . . . . ?
C5 C6 C7 C2 0.3(4) . . . . ?
C3 C2 C7 C6 0.0(4) . . . . ?
N1 C2 C7 C6 177.6(3) . . . . ?

_refine_diff_density_max         0.534
_refine_diff_density_min         -0.761
_refine_diff_density_rms         0.069

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_10april
_database_code_depnum_ccdc_archive 'CCDC 1483978'
_audit_update_record             
;
2016-06-07 deposited with the CCDC.
2016-08-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 I N2 S'
_chemical_formula_sum            'C13 H11 I N2 S'
_chemical_formula_weight         354.20

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'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.7772(11)
_cell_length_b                   5.1405(4)
_cell_length_c                   20.7792(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.085(5)
_cell_angle_gamma                90.00
_cell_volume                     1347.68(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4408
_cell_measurement_theta_min      3.97
_cell_measurement_theta_max      28.85

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.746
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    2.510
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.3979
_exptl_absorpt_correction_T_max  0.5614
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7967
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0402
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2301
_reflns_number_gt                2065
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0199P)²+3.6192P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2301
_refine_ls_number_parameters     162
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.0793
_refine_ls_wR_factor_gt          0.0770
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_restrained_S_all      1.186
_refine_ls_shift/su_max          0.001
_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
I1 I 0.63763(3) 0.65510(7) 0.755136(16) 0.02957(13) Uani 1 1 d . . .
S1 S 0.44884(10) 0.5921(2) 0.89717(5) 0.0243(3) Uani 1 1 d . . .
N1 N 0.5427(3) 0.2093(9) 0.84167(17) 0.0221(9) Uani 1 1 d . . .
N2 N 0.5963(3) 0.2650(8) 0.95142(19) 0.0222(9) Uani 1 1 d . . .
C1 C 0.5340(4) 0.3425(9) 0.8965(2) 0.0196(10) Uani 1 1 d . . .
C2 C 0.4738(4) 0.2510(9) 0.7811(2) 0.0183(10) Uani 1 1 d . . .
C3 C 0.4980(4) 0.4350(9) 0.7363(2) 0.0217(11) Uani 1 1 d . . .
C4 C 0.4306(4) 0.4708(10) 0.6779(2) 0.0280(12) Uani 1 1 d . . .
H4 H 0.4449 0.5987 0.6488 0.034 Uiso 1 1 calc R . .
C5 C 0.3420(4) 0.3143(11) 0.6632(2) 0.0311(12) Uani 1 1 d . . .
H5 H 0.2974 0.3344 0.6236 0.037 Uiso 1 1 calc R . .
C6 C 0.3193(4) 0.1289(10) 0.7068(2) 0.0273(11) Uani 1 1 d . . .
H6 H 0.2586 0.0276 0.6966 0.033 Uiso 1 1 calc R . .
C7 C 0.3840(4) 0.0913(10) 0.7647(2) 0.0259(12) Uani 1 1 d . . .
H7 H 0.3691 -0.0384 0.7931 0.031 Uiso 1 1 calc R . .
C8 C 0.6793(4) 0.0805(9) 0.9589(2) 0.0209(11) Uani 1 1 d . . .
C9 C 0.7575(4) 0.0847(11) 0.9201(3) 0.0359(14) Uani 1 1 d . . .
H9 H 0.7546 0.2054 0.8865 0.043 Uiso 1 1 calc R . .
C10 C 0.8395(5) -0.0900(13) 0.9313(3) 0.0495(17) Uani 1 1 d . . .
H10 H 0.8917 -0.0878 0.9048 0.059 Uiso 1 1 calc R . .
C11 C 0.8457(5) -0.2693(13) 0.9813(3) 0.0477(16) Uani 1 1 d . . .
H11 H 0.9010 -0.3887 0.9880 0.057 Uiso 1 1 calc R . .
C12 C 0.7691(5) -0.2695(11) 1.0212(3) 0.0363(13) Uani 1 1 d . . .
H12 H 0.7739 -0.3852 1.0559 0.044 Uiso 1 1 calc R . .
C13 C 0.6854(4) -0.0978(10) 1.0093(2) 0.0268(12) Uani 1 1 d . . .
H13 H 0.6327 -0.1016 1.0354 0.032 Uiso 1 1 calc R . .
H1 H 0.571(4) 0.059(12) 0.842(3) 0.034(16) Uiso 1 1 d . . .
H2 H 0.581(4) 0.321(10) 0.985(3) 0.024(14) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C3 2.096(5) . ?
S1 C1 1.684(5) . ?
N1 C1 1.349(6) . ?
N1 C2 1.433(6) . ?
N1 H1 0.85(6) . ?
N2 C1 1.344(6) . ?
N2 C8 1.413(6) . ?
N2 H2 0.80(5) . ?
C2 C3 1.395(7) . ?
C2 C7 1.408(7) . ?
C3 C4 1.385(7) . ?
C4 C5 1.384(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.362(7) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.379(7) . ?
C8 C13 1.385(6) . ?
C9 C10 1.372(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(7) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?

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
C1 N1 C2 123.0(4) . . ?
C1 N1 H1 123(4) . . ?
C2 N1 H1 110(4) . . ?
C1 N2 C8 128.7(4) . . ?
C1 N2 H2 116(4) . . ?
C8 N2 H2 115(4) . . ?
N2 C1 N1 116.7(4) . . ?
N2 C1 S1 121.1(3) . . ?
N1 C1 S1 122.2(3) . . ?
C3 C2 C7 119.4(4) . . ?
C3 C2 N1 121.2(4) . . ?
C7 C2 N1 119.3(4) . . ?
C4 C3 C2 120.2(5) . . ?
C4 C3 I1 119.0(4) . . ?
C2 C3 I1 120.9(3) . . ?
C5 C4 C3 119.3(5) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C6 C5 C4 120.5(5) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 121.2(5) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C2 119.3(5) . . ?
C6 C7 H7 120.4 . . ?
C2 C7 H7 120.4 . . ?
C9 C8 C13 119.5(5) . . ?
C9 C8 N2 121.7(4) . . ?
C13 C8 N2 118.6(4) . . ?
C10 C9 C8 119.7(5) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 121.1(5) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 119.4(5) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 119.8(5) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C8 120.5(5) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?

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
C8 N2 C1 N1 8.0(7) . . . . ?
C8 N2 C1 S1 -172.6(4) . . . . ?
C2 N1 C1 N2 173.2(4) . . . . ?
C2 N1 C1 S1 -6.2(7) . . . . ?
C1 N1 C2 C3 89.5(6) . . . . ?
C1 N1 C2 C7 -94.8(6) . . . . ?
C7 C2 C3 C4 3.9(7) . . . . ?
N1 C2 C3 C4 179.6(4) . . . . ?
C7 C2 C3 I1 -174.7(3) . . . . ?
N1 C2 C3 I1 0.9(6) . . . . ?
C2 C3 C4 C5 -2.9(7) . . . . ?
I1 C3 C4 C5 175.7(4) . . . . ?
C3 C4 C5 C6 1.6(8) . . . . ?
C4 C5 C6 C7 -1.2(8) . . . . ?
C5 C6 C7 C2 2.2(8) . . . . ?
C3 C2 C7 C6 -3.5(7) . . . . ?
N1 C2 C7 C6 -179.2(4) . . . . ?
C1 N2 C8 C9 48.1(8) . . . . ?
C1 N2 C8 C13 -136.2(5) . . . . ?
C13 C8 C9 C10 1.0(8) . . . . ?
N2 C8 C9 C10 176.7(5) . . . . ?
C8 C9 C10 C11 -0.6(10) . . . . ?
C9 C10 C11 C12 -1.1(10) . . . . ?
C10 C11 C12 C13 2.3(9) . . . . ?
C11 C12 C13 C8 -2.0(8) . . . . ?
C9 C8 C13 C12 0.3(7) . . . . ?
N2 C8 C13 C12 -175.5(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7 S1 0.93 2.94 3.759(5) 148.1 1_545
N2 H2 S1 0.80(5) 2.59(5) 3.368(4) 168(5) 3_667
N1 H1 I1 0.85(6) 2.96(6) 3.676(4) 143(4) 1_545

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.693
_refine_diff_density_min         -1.552
_refine_diff_density_rms         0.112
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 
'Dimethyl Formamide-Ethyl Acetate Mixture'
####################################################################### 
# 
# 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_RPG_04
_database_code_depnum_ccdc_archive 'CCDC 1483979'
_audit_update_record             
;
2016-07-21 deposited with the CCDC.
2016-08-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 I N2 O'
_chemical_formula_sum            'C13 H11 I N2 O'
_chemical_formula_weight         338.14

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   21.0485(13)
_cell_length_b                   4.6303(3)
_cell_length_c                   12.8294(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.835(4)
_cell_angle_gamma                90
_cell_volume                     1219.12(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6827
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      30.56

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.842
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    2.611
_shelx_estimated_absorpt_T_min   0.489
_shelx_estimated_absorpt_T_max   0.651
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.489
_exptl_absorpt_correction_T_max  0.651
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11390
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.985
_diffrn_reflns_theta_max         30.753
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.804
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.804
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.804
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             3066
_reflns_number_gt                2743
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0130P)²+3.1709P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3066
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.0713
_refine_ls_wR_factor_gt          0.0691
_refine_ls_goodness_of_fit_ref   1.225
_refine_ls_restrained_S_all      1.225
_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_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 0.58583(2) -0.33108(5) 0.47179(2) 0.02217(8) Uani 1 1 d . . . . .
O1 O 0.77425(13) 0.2961(5) 0.5484(2) 0.0229(6) Uani 1 1 d . . . . .
N1 N 0.73221(15) -0.1254(7) 0.4709(3) 0.0195(7) Uani 1 1 d . . . . .
N2 N 0.81048(16) -0.1332(7) 0.6259(3) 0.0223(7) Uani 1 1 d . . . . .
C1 C 0.77252(17) 0.0299(8) 0.5486(3) 0.0184(7) Uani 1 1 d . . . . .
C2 C 0.68718(17) 0.0024(8) 0.3846(3) 0.0181(7) Uani 1 1 d . . . . .
C3 C 0.62106(18) -0.0670(7) 0.3646(3) 0.0161(7) Uani 1 1 d . . . . .
C4 C 0.57795(19) 0.0492(8) 0.2766(3) 0.0194(8) Uani 1 1 d . . . . .
C5 C 0.60010(19) 0.2443(8) 0.2114(3) 0.0205(8) Uani 1 1 d . . . . .
C6 C 0.6649(2) 0.3204(9) 0.2325(3) 0.0230(8) Uani 1 1 d . . . . .
C7 C 0.70852(19) 0.1993(8) 0.3175(3) 0.0203(8) Uani 1 1 d . . . . .
C8 C 0.85344(17) -0.0210(8) 0.7183(3) 0.0184(7) Uani 1 1 d . . . . .
C9 C 0.89838(19) 0.1930(9) 0.7095(3) 0.0242(8) Uani 1 1 d . . . . .
C10 C 0.9406(2) 0.2909(9) 0.8017(4) 0.0309(10) Uani 1 1 d . . . . .
C11 C 0.9382(2) 0.1806(10) 0.9003(4) 0.0354(11) Uani 1 1 d . . . . .
C12 C 0.8938(2) -0.0335(10) 0.9081(3) 0.0311(10) Uani 1 1 d . . . . .
C13 C 0.8513(2) -0.1312(9) 0.8172(3) 0.0238(8) Uani 1 1 d . . . . .
H1 H 0.733(2) -0.294(11) 0.480(4) 0.032(13) Uiso 1 1 d . . . . .
H2 H 0.8055(19) -0.307(9) 0.620(3) 0.018(11) Uiso 1 1 d . . . . .
H4 H 0.534(2) 0.003(10) 0.263(3) 0.026(11) Uiso 1 1 d . . . . .
H5 H 0.572(2) 0.313(9) 0.154(3) 0.024(11) Uiso 1 1 d . . . . .
H6 H 0.6794(19) 0.447(9) 0.189(3) 0.022(11) Uiso 1 1 d . . . . .
H7 H 0.754(2) 0.243(10) 0.333(4) 0.032(13) Uiso 1 1 d . . . . .
H9 H 0.900(2) 0.258(10) 0.637(4) 0.031(12) Uiso 1 1 d . . . . .
H10 H 0.970(2) 0.427(11) 0.789(4) 0.042(14) Uiso 1 1 d . . . . .
H11 H 0.968(2) 0.242(9) 0.961(4) 0.028(12) Uiso 1 1 d . . . . .
H12 H 0.889(2) -0.109(10) 0.978(4) 0.039(13) Uiso 1 1 d . . . . .
H13 H 0.822(2) -0.270(9) 0.821(3) 0.023(11) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C3 2.095(4) . ?
O1 C1 1.233(4) . ?
N1 C1 1.362(5) . ?
N1 C2 1.417(4) . ?
N1 H1 0.79(5) . ?
N2 C1 1.357(5) . ?
N2 C8 1.419(5) . ?
N2 H2 0.81(4) . ?
C2 C3 1.395(5) . ?
C2 C7 1.395(5) . ?
C3 C4 1.391(5) . ?
C4 C5 1.381(6) . ?
C4 H4 0.93(4) . ?
C5 C6 1.377(6) . ?
C5 H5 0.90(4) . ?
C6 C7 1.379(5) . ?
C6 H6 0.91(4) . ?
C7 H7 0.95(4) . ?
C8 C13 1.379(5) . ?
C8 C9 1.392(5) . ?
C9 C10 1.389(6) . ?
C9 H9 0.98(5) . ?
C10 C11 1.376(7) . ?
C10 H10 0.93(5) . ?
C11 C12 1.382(7) . ?
C11 H11 0.93(4) . ?
C12 C13 1.378(6) . ?
C12 H12 0.98(5) . ?
C13 H13 0.90(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 123.4(3) . . ?
C1 N1 H1 115(3) . . ?
C2 N1 H1 121(3) . . ?
C1 N2 C8 124.7(3) . . ?
C1 N2 H2 116(3) . . ?
C8 N2 H2 119(3) . . ?
O1 C1 N2 123.0(3) . . ?
O1 C1 N1 122.7(3) . . ?
N2 C1 N1 114.3(3) . . ?
C3 C2 C7 118.8(3) . . ?
C3 C2 N1 120.9(3) . . ?
C7 C2 N1 120.3(3) . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 I1 119.8(3) . . ?
C2 C3 I1 119.9(3) . . ?
C5 C4 C3 119.9(4) . . ?
C5 C4 H4 120(3) . . ?
C3 C4 H4 121(3) . . ?
C6 C5 C4 120.1(4) . . ?
C6 C5 H5 121(3) . . ?
C4 C5 H5 118(3) . . ?
C5 C6 C7 120.5(4) . . ?
C5 C6 H6 120(2) . . ?
C7 C6 H6 120(2) . . ?
C6 C7 C2 120.3(4) . . ?
C6 C7 H7 123(3) . . ?
C2 C7 H7 117(3) . . ?
C13 C8 C9 120.0(3) . . ?
C13 C8 N2 119.2(3) . . ?
C9 C8 N2 120.8(3) . . ?
C10 C9 C8 118.8(4) . . ?
C10 C9 H9 124(3) . . ?
C8 C9 H9 117(3) . . ?
C11 C10 C9 121.0(4) . . ?
C11 C10 H10 125(3) . . ?
C9 C10 H10 114(3) . . ?
C10 C11 C12 119.8(4) . . ?
C10 C11 H11 121(3) . . ?
C12 C11 H11 119(3) . . ?
C13 C12 C11 119.8(4) . . ?
C13 C12 H12 119(3) . . ?
C11 C12 H12 121(3) . . ?
C12 C13 C8 120.6(4) . . ?
C12 C13 H13 121(3) . . ?
C8 C13 H13 118(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
C8 N2 C1 O1 4.0(6) . . . . ?
C8 N2 C1 N1 -176.1(3) . . . . ?
C2 N1 C1 O1 -2.1(6) . . . . ?
C2 N1 C1 N2 178.0(3) . . . . ?
C1 N1 C2 C3 -124.6(4) . . . . ?
C1 N1 C2 C7 55.9(5) . . . . ?
C7 C2 C3 C4 2.7(5) . . . . ?
N1 C2 C3 C4 -176.8(3) . . . . ?
C7 C2 C3 I1 -174.3(3) . . . . ?
N1 C2 C3 I1 6.2(5) . . . . ?
C2 C3 C4 C5 -3.0(5) . . . . ?
I1 C3 C4 C5 174.0(3) . . . . ?
C3 C4 C5 C6 1.0(6) . . . . ?
C4 C5 C6 C7 1.1(6) . . . . ?
C5 C6 C7 C2 -1.4(6) . . . . ?
C3 C2 C7 C6 -0.6(6) . . . . ?
N1 C2 C7 C6 179.0(4) . . . . ?
C1 N2 C8 C13 130.6(4) . . . . ?
C1 N2 C8 C9 -50.9(6) . . . . ?
C13 C8 C9 C10 0.2(6) . . . . ?
N2 C8 C9 C10 -178.3(4) . . . . ?
C8 C9 C10 C11 -0.3(6) . . . . ?
C9 C10 C11 C12 0.9(7) . . . . ?
C10 C11 C12 C13 -1.3(7) . . . . ?
C11 C12 C13 C8 1.2(6) . . . . ?
C9 C8 C13 C12 -0.6(6) . . . . ?
N2 C8 C13 C12 177.9(4) . . . . ?

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
N2 H2 O1 0.81(4) 2.09(4) 2.866(4) 158(4) 1_545
N1 H1 O1 0.79(5) 2.19(5) 2.925(4) 155(4) 1_545

_refine_diff_density_max         1.110
_refine_diff_density_min         -1.830
_refine_diff_density_rms         0.125

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_ASD
_database_code_depnum_ccdc_archive 'CCDC 1483980'
_audit_update_record             
;
2016-07-21 deposited with the CCDC.
2016-08-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 I N2 S'
_chemical_formula_sum            'C13 H11 I N2 S'
_chemical_formula_weight         354.20

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.6626(17)
_cell_length_b                   7.0591(10)
_cell_length_c                   15.395(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.006(2)
_cell_angle_gamma                90
_cell_volume                     1372.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9917
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      31.24

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.380
_exptl_absorpt_coefficient_mu    2.464
_shelx_estimated_absorpt_T_min   0.397
_shelx_estimated_absorpt_T_max   0.454
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.397
_exptl_absorpt_correction_T_max  0.454
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19962
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.015
_diffrn_reflns_theta_max         31.568
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4367
_reflns_number_gt                3650
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0499P)²+3.3352P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4367
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1354
_refine_ls_wR_factor_gt          0.1309
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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_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 0.86077(3) 0.77465(5) 0.46100(2) 0.06354(14) Uani 1 1 d . . . . .
S1 S 0.98860(9) 0.91644(14) 0.13481(6) 0.0433(2) Uani 1 1 d . . . . .
N1 N 0.8515(2) 0.6318(4) 0.11131(18) 0.0366(6) Uani 1 1 d . . . . .
H1 H 0.8037 0.5724 0.0771 0.044 Uiso 1 1 d R U . . .
N2 N 0.8758(3) 0.8148(5) -0.0078(2) 0.0454(8) Uani 1 1 d . . . . .
H2 H 0.9023 0.9181 -0.0297 0.054 Uiso 1 1 d R U . . .
C1 C 0.9003(3) 0.7797(5) 0.0770(2) 0.0339(6) Uani 1 1 d . . . . .
C2 C 0.8695(3) 0.5605(5) 0.1979(2) 0.0339(6) Uani 1 1 d . . . . .
C3 C 0.8566(3) 0.6765(5) 0.2695(2) 0.0354(7) Uani 1 1 d . . . . .
H3 H 0.8366 0.8054 0.2617 0.042 Uiso 1 1 calc R U . . .
C4 C 0.8733(3) 0.6010(6) 0.3520(2) 0.0398(7) Uani 1 1 d . . . . .
C5 C 0.8997(3) 0.4123(6) 0.3647(3) 0.0477(9) Uani 1 1 d . . . . .
H5 H 0.9105 0.3619 0.4219 0.057 Uiso 1 1 calc R U . . .
C6 C 0.9100(4) 0.2979(6) 0.2925(3) 0.0495(9) Uani 1 1 d . . . . .
H6 H 0.9272 0.1677 0.3004 0.059 Uiso 1 1 calc R U . . .
C7 C 0.8956(3) 0.3713(5) 0.2088(3) 0.0416(7) Uani 1 1 d . . . . .
H7 H 0.9035 0.2925 0.1597 0.050 Uiso 1 1 calc R U . . .
C8 C 0.8096(3) 0.7002(6) -0.0656(2) 0.0384(7) Uani 1 1 d . . . . .
C9 C 0.7108(4) 0.7639(7) -0.0965(3) 0.0526(11) Uani 1 1 d . . . . .
H9 H 0.6853 0.8829 -0.0782 0.063 Uiso 1 1 calc R U . . .
C10 C 0.6491(4) 0.6522(9) -0.1548(3) 0.0603(13) Uani 1 1 d . . . . .
H10 H 0.5811 0.6956 -0.1760 0.072 Uiso 1 1 calc R U . . .
C11 C 0.6851(4) 0.4807(8) -0.1818(3) 0.0564(11) Uani 1 1 d . . . . .
H11 H 0.6426 0.4065 -0.2221 0.068 Uiso 1 1 calc R U . . .
C12 C 0.7827(4) 0.4158(8) -0.1508(3) 0.0588(12) Uani 1 1 d . . . . .
H12 H 0.8074 0.2959 -0.1688 0.071 Uiso 1 1 calc R U . . .
C13 C 0.8451(3) 0.5258(7) -0.0930(3) 0.0496(9) Uani 1 1 d . . . . .
H13 H 0.9130 0.4813 -0.0719 0.060 Uiso 1 1 calc R U . . .


_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 C4 2.094(4) . ?
S1 C1 1.684(4) . ?
N1 C1 1.340(5) . ?
N1 C2 1.428(4) . ?
N1 H1 0.8803 . ?
N2 C1 1.345(4) . ?
N2 C8 1.430(5) . ?
N2 H2 0.8797 . ?
C2 C7 1.384(5) . ?
C2 C3 1.391(5) . ?
C3 C4 1.380(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(6) . ?
C5 C6 1.388(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(6) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.382(6) . ?
C8 C13 1.386(6) . ?
C9 C10 1.392(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.369(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.372(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(6) . ?
C12 H12 0.9500 . ?
C13 H13 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
C1 N1 C2 126.4(3) . . ?
C1 N1 H1 116.9 . . ?
C2 N1 H1 116.7 . . ?
C1 N2 C8 125.8(3) . . ?
C1 N2 H2 117.2 . . ?
C8 N2 H2 117.0 . . ?
N1 C1 N2 116.4(3) . . ?
N1 C1 S1 123.1(2) . . ?
N2 C1 S1 120.5(3) . . ?
C7 C2 C3 120.8(3) . . ?
C7 C2 N1 118.3(3) . . ?
C3 C2 N1 120.8(3) . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 121.5(4) . . ?
C3 C4 I1 119.8(3) . . ?
C5 C4 I1 118.8(3) . . ?
C4 C5 C6 118.8(4) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C7 120.8(4) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C2 C7 C6 119.2(4) . . ?
C2 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C9 C8 C13 119.3(4) . . ?
C9 C8 N2 120.4(4) . . ?
C13 C8 N2 120.2(3) . . ?
C8 C9 C10 119.4(4) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 120.9(4) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 120.0(4) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 119.7(5) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C8 C13 C12 120.7(4) . . ?
C8 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?

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
C2 N1 C1 N2 175.9(4) . . . . ?
C2 N1 C1 S1 -3.7(5) . . . . ?
C8 N2 C1 N1 -5.4(6) . . . . ?
C8 N2 C1 S1 174.2(3) . . . . ?
C1 N1 C2 C7 -124.9(4) . . . . ?
C1 N1 C2 C3 57.9(5) . . . . ?
C7 C2 C3 C4 1.9(5) . . . . ?
N1 C2 C3 C4 179.0(3) . . . . ?
C2 C3 C4 C5 -1.7(6) . . . . ?
C2 C3 C4 I1 177.4(3) . . . . ?
C3 C4 C5 C6 0.4(6) . . . . ?
I1 C4 C5 C6 -178.7(3) . . . . ?
C4 C5 C6 C7 0.8(7) . . . . ?
C3 C2 C7 C6 -0.7(6) . . . . ?
N1 C2 C7 C6 -177.9(4) . . . . ?
C5 C6 C7 C2 -0.7(7) . . . . ?
C1 N2 C8 C9 110.1(5) . . . . ?
C1 N2 C8 C13 -71.6(5) . . . . ?
C13 C8 C9 C10 -0.3(7) . . . . ?
N2 C8 C9 C10 178.1(4) . . . . ?
C8 C9 C10 C11 -0.1(7) . . . . ?
C9 C10 C11 C12 0.7(8) . . . . ?
C10 C11 C12 C13 -0.9(8) . . . . ?
C9 C8 C13 C12 0.1(6) . . . . ?
N2 C8 C13 C12 -178.3(4) . . . . ?
C11 C12 C13 C8 0.5(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
C7 H7 S1 0.95 2.90 3.631(4) 134.6 1_545
N2 H2 S1 0.88 2.49 3.292(4) 151.8 3_775
N1 H1 I1 0.88 2.99 3.795(3) 153.3 2_645

_refine_diff_density_max         2.441
_refine_diff_density_min         -1.578
_refine_diff_density_rms         0.106

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_ABC
_database_code_depnum_ccdc_archive 'CCDC 1483981'
_audit_update_record             
;
2016-07-21 deposited with the CCDC.
2016-08-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 F I N2 O'
_chemical_formula_sum            'C13 H10 F I N2 O'
_chemical_formula_weight         356.13

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   27.607(6)
_cell_length_b                   4.6224(11)
_cell_length_c                   9.750(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.235(3)
_cell_angle_gamma                90
_cell_volume                     1242.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    8176
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      31.50

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.904
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.270
_exptl_absorpt_coefficient_mu    2.579
_shelx_estimated_absorpt_T_min   0.377
_shelx_estimated_absorpt_T_max   0.543
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.377
_exptl_absorpt_correction_T_max  0.543
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18098
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.217
_diffrn_reflns_theta_max         31.636
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3985
_reflns_number_gt                3323
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0381P)²+0.7356P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3985
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.0834
_refine_ls_wR_factor_gt          0.0792
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_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_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 0.45271(2) 0.73638(3) 0.15065(2) 0.04412(7) Uani 1 1 d . . . . .
F1 F 0.02928(7) 0.2447(3) 0.4659(2) 0.0515(4) Uani 1 1 d . . . . .
O1 O 0.22112(5) 0.3269(3) 0.17274(15) 0.0271(3) Uani 1 1 d . . . . .
N1 N 0.25630(6) 0.7548(3) 0.11617(19) 0.0247(3) Uani 1 1 d . . . . .
H1 H 0.2532 0.9441 0.1126 0.030 Uiso 1 1 calc R U . . .
N2 N 0.18464(7) 0.7528(3) 0.22467(19) 0.0259(3) Uani 1 1 d . . . . .
H2 H 0.1860 0.9427 0.2198 0.031 Uiso 1 1 calc R U . . .
C4 C 0.38510(6) 0.5948(4) 0.06677(19) 0.0259(3) Uani 1 1 d . . . . .
C3 C 0.34355(7) 0.7161(3) 0.11719(19) 0.0233(3) Uani 1 1 d . . . . .
H3 H 0.3462 0.8589 0.1873 0.028 Uiso 1 1 calc R U . . .
C2 C 0.29815(6) 0.6267(3) 0.06422(17) 0.0204(3) Uani 1 1 d . . . . .
C7 C 0.29469(7) 0.4177(4) -0.03911(18) 0.0254(3) Uani 1 1 d . . . . .
H7 H 0.2638 0.3584 -0.0770 0.031 Uiso 1 1 calc R U . . .
C6 C 0.33668(9) 0.2971(4) -0.0862(2) 0.0302(4) Uani 1 1 d . . . . .
H6 H 0.3342 0.1524 -0.1554 0.036 Uiso 1 1 calc R U . . .
C5 C 0.38204(7) 0.3835(4) -0.0343(2) 0.0301(4) Uani 1 1 d . . . . .
H5 H 0.4106 0.2997 -0.0672 0.036 Uiso 1 1 calc R U . . .
C1 C 0.22066(6) 0.5954(3) 0.17149(17) 0.0207(3) Uani 1 1 d . . . . .
C8 C 0.14479(6) 0.6234(3) 0.28785(17) 0.0212(3) Uani 1 1 d . . . . .
C9 C 0.15267(7) 0.4195(4) 0.39198(18) 0.0261(3) Uani 1 1 d . . . . .
H9 H 0.1849 0.3686 0.4222 0.031 Uiso 1 1 calc R U . . .
C10 C 0.11370(9) 0.2908(4) 0.4515(2) 0.0313(4) Uani 1 1 d . . . . .
H10 H 0.1188 0.1484 0.5210 0.038 Uiso 1 1 calc R U . . .
C11 C 0.06742(7) 0.3731(4) 0.4081(2) 0.0312(4) Uani 1 1 d . . . . .
C12 C 0.05841(7) 0.5792(5) 0.3084(2) 0.0335(4) Uani 1 1 d . . . . .
H12 H 0.0261 0.6358 0.2821 0.040 Uiso 1 1 calc R U . . .
C13 C 0.09772(8) 0.7035(4) 0.2469(2) 0.0288(4) Uani 1 1 d . . . . .
H13 H 0.0923 0.8437 0.1765 0.035 Uiso 1 1 calc R U . . .


_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 C4 2.0996(18) . ?
F1 C11 1.358(2) . ?
O1 C1 1.241(2) . ?
N1 C1 1.364(2) . ?
N1 C2 1.417(2) . ?
N1 H1 0.8800 . ?
N2 C1 1.359(2) . ?
N2 C8 1.423(2) . ?
N2 H2 0.8800 . ?
C4 C5 1.386(3) . ?
C4 C3 1.391(3) . ?
C3 C2 1.391(2) . ?
C3 H3 0.9500 . ?
C2 C7 1.395(2) . ?
C7 C6 1.387(3) . ?
C7 H7 0.9500 . ?
C6 C5 1.383(3) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
C8 C13 1.388(3) . ?
C8 C9 1.393(2) . ?
C9 C10 1.385(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.374(3) . ?
C12 C13 1.393(3) . ?
C12 H12 0.9500 . ?
C13 H13 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
C1 N1 C2 122.44(13) . . ?
C1 N1 H1 118.8 . . ?
C2 N1 H1 118.8 . . ?
C1 N2 C8 122.72(13) . . ?
C1 N2 H2 118.6 . . ?
C8 N2 H2 118.6 . . ?
C5 C4 C3 121.10(17) . . ?
C5 C4 I1 120.90(14) . . ?
C3 C4 I1 117.99(13) . . ?
C2 C3 C4 119.52(16) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C2 C7 119.80(16) . . ?
C3 C2 N1 118.62(15) . . ?
C7 C2 N1 121.57(16) . . ?
C6 C7 C2 119.52(17) . . ?
C6 C7 H7 120.2 . . ?
C2 C7 H7 120.2 . . ?
C5 C6 C7 121.28(18) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C6 C5 C4 118.75(18) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
O1 C1 N2 122.63(16) . . ?
O1 C1 N1 122.46(16) . . ?
N2 C1 N1 114.91(14) . . ?
C13 C8 C9 119.68(17) . . ?
C13 C8 N2 119.84(16) . . ?
C9 C8 N2 120.48(16) . . ?
C10 C9 C8 120.19(17) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 118.81(18) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
F1 C11 C12 118.87(19) . . ?
F1 C11 C10 118.66(19) . . ?
C12 C11 C10 122.47(18) . . ?
C11 C12 C13 118.44(18) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C8 C13 C12 120.37(17) . . ?
C8 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C4 C3 C2 -0.8(3) . . . . ?
I1 C4 C3 C2 -179.82(12) . . . . ?
C4 C3 C2 C7 -0.3(3) . . . . ?
C4 C3 C2 N1 -179.47(15) . . . . ?
C1 N1 C2 C3 -123.72(19) . . . . ?
C1 N1 C2 C7 57.1(2) . . . . ?
C3 C2 C7 C6 1.2(3) . . . . ?
N1 C2 C7 C6 -179.61(16) . . . . ?
C2 C7 C6 C5 -1.1(3) . . . . ?
C7 C6 C5 C4 0.0(3) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
I1 C4 C5 C6 179.90(14) . . . . ?
C8 N2 C1 O1 0.9(3) . . . . ?
C8 N2 C1 N1 -179.30(17) . . . . ?
C2 N1 C1 O1 -4.3(3) . . . . ?
C2 N1 C1 N2 175.86(17) . . . . ?
C1 N2 C8 C13 -128.84(19) . . . . ?
C1 N2 C8 C9 52.0(3) . . . . ?
C13 C8 C9 C10 1.9(3) . . . . ?
N2 C8 C9 C10 -178.94(16) . . . . ?
C8 C9 C10 C11 -1.5(3) . . . . ?
C9 C10 C11 F1 179.47(18) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
F1 C11 C12 C13 -178.13(19) . . . . ?
C10 C11 C12 C13 1.7(3) . . . . ?
C9 C8 C13 C12 -0.6(3) . . . . ?
N2 C8 C13 C12 -179.71(17) . . . . ?
C11 C12 C13 C8 -1.2(3) . . . . ?

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
N2 H2 O1 0.88 2.09 2.8932(19) 152.0 1_565
N1 H1 O1 0.88 2.08 2.8813(19) 151.4 1_565

_refine_diff_density_max         1.378
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.085

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_10_2116_0m
_database_code_depnum_ccdc_archive 'CCDC 1483982'
_audit_update_record             
;
2016-07-21 deposited with the CCDC.
2016-08-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H13 I N2 O S'
_chemical_formula_sum            'C14 H13 I N2 O S'
_chemical_formula_weight         384.22

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.481(2)
_cell_length_b                   9.9446(16)
_cell_length_c                   23.867(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.736(2)
_cell_angle_gamma                90
_cell_volume                     2941.9(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9970
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      31.18

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_F_000             1504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.260
_exptl_absorpt_coefficient_mu    2.312
_shelx_estimated_absorpt_T_min   0.490
_shelx_estimated_absorpt_T_max   0.585
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.490
_exptl_absorpt_correction_T_max  0.585
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43395
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.221
_diffrn_reflns_theta_max         31.578
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9334
_reflns_number_gt                8270
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0338P)²+11.9042P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9334
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1300
_refine_ls_wR_factor_gt          0.1265
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_restrained_S_all      1.181
_refine_ls_shift/su_max          0.001
_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_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 0.36402(2) 0.76453(3) 0.73180(2) 0.03429(9) Uani 1 1 d . . . . .
I1' I 1.08510(3) 0.70738(4) 0.10836(2) 0.04359(10) Uani 1 1 d . . . . .
S1 S 0.28231(7) 0.85752(10) 0.50693(4) 0.02401(18) Uani 1 1 d . . . . .
S1' S 1.19951(8) 0.84601(13) 0.32902(4) 0.0306(2) Uani 1 1 d . . . . .
O1 O 0.7728(2) 0.6904(3) 0.32469(11) 0.0242(5) Uani 1 1 d . . . . .
O1' O 0.7108(2) 0.6501(3) 0.50711(12) 0.0268(6) Uani 1 1 d . . . . .
N1 N 0.4920(2) 0.7826(4) 0.51763(13) 0.0227(6) Uani 1 1 d . . . . .
H1 H 0.5462 0.7541 0.5003 0.027 Uiso 1 1 calc R U . . .
N2 N 0.4017(2) 0.7813(3) 0.42866(13) 0.0223(6) Uani 1 1 d . . . . .
H2 H 0.3400 0.7840 0.4067 0.027 Uiso 1 1 calc R U . . .
N1' N 0.9863(3) 0.8021(4) 0.32236(13) 0.0253(7) Uani 1 1 d . . . . .
H1' H 0.9306 0.7831 0.3404 0.030 Uiso 1 1 calc R U . . .
N2' N 1.0830(3) 0.7704(4) 0.40852(14) 0.0296(8) Uani 1 1 d . . . . .
H2' H 1.1455 0.7680 0.4298 0.035 Uiso 1 1 calc R U . . .
C4 C 0.4750(3) 0.7913(4) 0.67269(16) 0.0264(8) Uani 1 1 d . . . . .
C3 C 0.4418(3) 0.7718(4) 0.61547(15) 0.0216(7) Uani 1 1 d . . . . .
H3 H 0.3711 0.7406 0.6029 0.026 Uiso 1 1 calc R U . . .
C2 C 0.5151(3) 0.7992(4) 0.57697(15) 0.0207(6) Uani 1 1 d . . . . .
C7 C 0.6200(3) 0.8397(4) 0.59659(16) 0.0267(8) Uani 1 1 d . . . . .
H7 H 0.6697 0.8589 0.5704 0.032 Uiso 1 1 calc R U . . .
C6 C 0.6520(3) 0.8520(5) 0.65395(19) 0.0349(10) Uani 1 1 d . . . . .
H6 H 0.7242 0.8767 0.6669 0.042 Uiso 1 1 calc R U . . .
C5 C 0.5794(4) 0.8285(5) 0.69245(18) 0.0358(10) Uani 1 1 d . . . . .
H5 H 0.6008 0.8379 0.7318 0.043 Uiso 1 1 calc R U . . .
C1 C 0.3985(3) 0.8041(4) 0.48378(14) 0.0190(6) Uani 1 1 d . . . . .
C8 C 0.4967(3) 0.7530(4) 0.40233(14) 0.0183(6) Uani 1 1 d . . . . .
C9 C 0.5678(3) 0.8574(4) 0.39413(17) 0.0259(7) Uani 1 1 d . . . . .
H9 H 0.5531 0.9456 0.4065 0.031 Uiso 1 1 calc R U . . .
C10 C 0.6594(3) 0.8343(4) 0.36822(17) 0.0268(8) Uani 1 1 d . . . . .
H10 H 0.7079 0.9057 0.3633 0.032 Uiso 1 1 calc R U . . .
C11 C 0.6801(3) 0.7040(4) 0.34913(14) 0.0199(6) Uani 1 1 d . . . . .
C12 C 0.6083(3) 0.5991(4) 0.35632(15) 0.0223(7) Uani 1 1 d . . . . .
H12 H 0.6216 0.5112 0.3432 0.027 Uiso 1 1 calc R U . . .
C13 C 0.5166(3) 0.6257(4) 0.38309(15) 0.0220(7) Uani 1 1 d . . . . .
H13 H 0.4673 0.5551 0.3881 0.026 Uiso 1 1 calc R U . . .
C14 C 0.7983(3) 0.5588(4) 0.30532(18) 0.0291(8) Uani 1 1 d . . . . .
H14A H 0.8055 0.4961 0.3372 0.044 Uiso 1 1 calc R U . . .
H14B H 0.8664 0.5624 0.2887 0.044 Uiso 1 1 calc R U . . .
H14C H 0.7404 0.5282 0.2769 0.044 Uiso 1 1 calc R U . . .
C4' C 0.9906(4) 0.7886(5) 0.16754(17) 0.0300(8) Uani 1 1 d . . . . .
C3' C 1.0222(3) 0.7660(4) 0.22448(16) 0.0267(7) Uani 1 1 d . . . . .
H3' H 1.0825 0.7105 0.2365 0.032 Uiso 1 1 calc R U . . .
C2' C 0.9629(3) 0.8270(4) 0.26357(16) 0.0255(7) Uani 1 1 d . . . . .
C7' C 0.8741(3) 0.9068(5) 0.24569(18) 0.0337(9) Uani 1 1 d . . . . .
H7' H 0.8351 0.9494 0.2726 0.040 Uiso 1 1 calc R U . . .
C6' C 0.8426(4) 0.9241(6) 0.1884(2) 0.0405(11) Uani 1 1 d . . . . .
H6' H 0.7811 0.9774 0.1761 0.049 Uiso 1 1 calc R U . . .
C5' C 0.9005(4) 0.8642(5) 0.14887(18) 0.0369(10) Uani 1 1 d . . . . .
H5' H 0.8785 0.8749 0.1097 0.044 Uiso 1 1 calc R U . . .
C1' C 1.0833(3) 0.8038(4) 0.35397(15) 0.0230(7) Uani 1 1 d . . . . .
C8' C 0.9881(3) 0.7381(4) 0.43452(15) 0.0215(7) Uani 1 1 d . . . . .
C13' C 0.9292(3) 0.8383(4) 0.45737(17) 0.0286(8) Uani 1 1 d . . . . .
H13' H 0.9523 0.9293 0.4565 0.034 Uiso 1 1 calc R U . . .
C12' C 0.8372(3) 0.8064(4) 0.48136(18) 0.0279(8) Uani 1 1 d . . . . .
H12' H 0.7961 0.8755 0.4961 0.033 Uiso 1 1 calc R U . . .
C11' C 0.8048(3) 0.6742(4) 0.48396(14) 0.0192(6) Uani 1 1 d . . . . .
C10' C 0.8643(3) 0.5715(4) 0.46217(16) 0.0237(7) Uani 1 1 d . . . . .
H10' H 0.8423 0.4804 0.4642 0.028 Uiso 1 1 calc R U . . .
C9' C 0.9561(3) 0.6053(4) 0.43755(17) 0.0272(8) Uani 1 1 d . . . . .
H9' H 0.9974 0.5365 0.4227 0.033 Uiso 1 1 calc R U . . .
C14' C 0.6789(4) 0.5142(5) 0.5136(2) 0.0357(10) Uani 1 1 d . . . . .
H14D H 0.6659 0.4714 0.4764 0.053 Uiso 1 1 calc R U . . .
H14E H 0.6126 0.5118 0.5319 0.053 Uiso 1 1 calc R U . . .
H14F H 0.7363 0.4659 0.5369 0.053 Uiso 1 1 calc R U . . .


_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 C4 2.107(4) . ?
I1' C4' 2.104(4) . ?
S1 C1 1.696(4) . ?
S1' C1' 1.685(4) . ?
O1 C11 1.362(4) . ?
O1 C14 1.436(5) . ?
O1' C11' 1.375(4) . ?
O1' C14' 1.422(5) . ?
N1 C1 1.356(5) . ?
N1 C2 1.421(5) . ?
N1 H1 0.8800 . ?
N2 C1 1.340(4) . ?
N2 C8 1.434(4) . ?
N2 H2 0.8800 . ?
N1' C1' 1.349(5) . ?
N1' C2' 1.421(5) . ?
N1' H1' 0.8800 . ?
N2' C1' 1.344(5) . ?
N2' C8' 1.436(4) . ?
N2' H2' 0.8800 . ?
C4 C5 1.383(6) . ?
C4 C3 1.393(5) . ?
C3 C2 1.398(5) . ?
C3 H3 0.9500 . ?
C2 C7 1.397(5) . ?
C7 C6 1.386(6) . ?
C7 H7 0.9500 . ?
C6 C5 1.385(6) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
C8 C13 1.379(5) . ?
C8 C9 1.394(5) . ?
C9 C10 1.381(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.408(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.398(5) . ?
C12 C13 1.401(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C4' C5' 1.383(7) . ?
C4' C3' 1.388(5) . ?
C3' C2' 1.395(6) . ?
C3' H3' 0.9500 . ?
C2' C7' 1.389(6) . ?
C7' C6' 1.389(6) . ?
C7' H7' 0.9500 . ?
C6' C5' 1.388(7) . ?
C6' H6' 0.9500 . ?
C5' H5' 0.9500 . ?
C8' C9' 1.385(6) . ?
C8' C13' 1.388(6) . ?
C13' C12' 1.379(5) . ?
C13' H13' 0.9500 . ?
C12' C11' 1.379(5) . ?
C12' H12' 0.9500 . ?
C11' C10' 1.398(5) . ?
C10' C9' 1.389(5) . ?
C10' H10' 0.9500 . ?
C9' H9' 0.9500 . ?
C14' H14D 0.9800 . ?
C14' H14E 0.9800 . ?
C14' H14F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C14 117.3(3) . . ?
C11' O1' C14' 118.1(3) . . ?
C1 N1 C2 129.4(3) . . ?
C1 N1 H1 115.3 . . ?
C2 N1 H1 115.3 . . ?
C1 N2 C8 125.8(3) . . ?
C1 N2 H2 117.1 . . ?
C8 N2 H2 117.1 . . ?
C1' N1' C2' 128.1(3) . . ?
C1' N1' H1' 116.0 . . ?
C2' N1' H1' 116.0 . . ?
C1' N2' C8' 124.7(3) . . ?
C1' N2' H2' 117.6 . . ?
C8' N2' H2' 117.6 . . ?
C5 C4 C3 122.1(4) . . ?
C5 C4 I1 118.2(3) . . ?
C3 C4 I1 119.7(3) . . ?
C4 C3 C2 118.3(3) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C7 C2 C3 119.7(3) . . ?
C7 C2 N1 116.1(3) . . ?
C3 C2 N1 124.1(3) . . ?
C6 C7 C2 120.5(4) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
C5 C6 C7 120.3(4) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C4 C5 C6 118.9(4) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
N2 C1 N1 115.8(3) . . ?
N2 C1 S1 119.8(3) . . ?
N1 C1 S1 124.3(3) . . ?
C13 C8 C9 119.7(3) . . ?
C13 C8 N2 121.1(3) . . ?
C9 C8 N2 119.2(3) . . ?
C10 C9 C8 120.8(4) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 119.5(4) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
O1 C11 C12 124.6(3) . . ?
O1 C11 C10 115.3(3) . . ?
C12 C11 C10 120.1(3) . . ?
C11 C12 C13 119.0(3) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C8 C13 C12 120.9(3) . . ?
C8 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5' C4' C3' 122.0(4) . . ?
C5' C4' I1' 119.4(3) . . ?
C3' C4' I1' 118.6(3) . . ?
C4' C3' C2' 118.2(4) . . ?
C4' C3' H3' 120.9 . . ?
C2' C3' H3' 120.9 . . ?
C7' C2' C3' 120.6(4) . . ?
C7' C2' N1' 117.8(4) . . ?
C3' C2' N1' 121.4(4) . . ?
C2' C7' C6' 119.8(4) . . ?
C2' C7' H7' 120.1 . . ?
C6' C7' H7' 120.1 . . ?
C5' C6' C7' 120.4(4) . . ?
C5' C6' H6' 119.8 . . ?
C7' C6' H6' 119.8 . . ?
C4' C5' C6' 118.9(4) . . ?
C4' C5' H5' 120.5 . . ?
C6' C5' H5' 120.5 . . ?
N2' C1' N1' 115.8(3) . . ?
N2' C1' S1' 120.3(3) . . ?
N1' C1' S1' 124.0(3) . . ?
C9' C8' C13' 119.7(3) . . ?
C9' C8' N2' 119.5(4) . . ?
C13' C8' N2' 120.8(4) . . ?
C12' C13' C8' 120.2(4) . . ?
C12' C13' H13' 119.9 . . ?
C8' C13' H13' 119.9 . . ?
C13' C12' C11' 120.1(4) . . ?
C13' C12' H12' 120.0 . . ?
C11' C12' H12' 120.0 . . ?
O1' C11' C12' 116.9(3) . . ?
O1' C11' C10' 122.5(3) . . ?
C12' C11' C10' 120.5(3) . . ?
C9' C10' C11' 118.8(4) . . ?
C9' C10' H10' 120.6 . . ?
C11' C10' H10' 120.6 . . ?
C8' C9' C10' 120.7(4) . . ?
C8' C9' H9' 119.7 . . ?
C10' C9' H9' 119.7 . . ?
O1' C14' H14D 109.5 . . ?
O1' C14' H14E 109.5 . . ?
H14D C14' H14E 109.5 . . ?
O1' C14' H14F 109.5 . . ?
H14D C14' H14F 109.5 . . ?
H14E C14' H14F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C4 C3 C2 -4.1(6) . . . . ?
I1 C4 C3 C2 175.7(3) . . . . ?
C4 C3 C2 C7 2.6(6) . . . . ?
C4 C3 C2 N1 179.5(4) . . . . ?
C1 N1 C2 C7 -147.0(4) . . . . ?
C1 N1 C2 C3 36.1(6) . . . . ?
C3 C2 C7 C6 0.4(6) . . . . ?
N1 C2 C7 C6 -176.7(4) . . . . ?
C2 C7 C6 C5 -2.1(7) . . . . ?
C3 C4 C5 C6 2.4(8) . . . . ?
I1 C4 C5 C6 -177.3(4) . . . . ?
C7 C6 C5 C4 0.7(8) . . . . ?
C8 N2 C1 N1 -8.1(5) . . . . ?
C8 N2 C1 S1 171.5(3) . . . . ?
C2 N1 C1 N2 179.0(4) . . . . ?
C2 N1 C1 S1 -0.6(6) . . . . ?
C1 N2 C8 C13 107.4(5) . . . . ?
C1 N2 C8 C9 -75.2(5) . . . . ?
C13 C8 C9 C10 -1.6(6) . . . . ?
N2 C8 C9 C10 -179.1(4) . . . . ?
C8 C9 C10 C11 1.0(6) . . . . ?
C14 O1 C11 C12 -0.3(5) . . . . ?
C14 O1 C11 C10 179.1(3) . . . . ?
C9 C10 C11 O1 -179.3(4) . . . . ?
C9 C10 C11 C12 0.1(6) . . . . ?
O1 C11 C12 C13 178.8(3) . . . . ?
C10 C11 C12 C13 -0.5(6) . . . . ?
C9 C8 C13 C12 1.2(6) . . . . ?
N2 C8 C13 C12 178.6(3) . . . . ?
C11 C12 C13 C8 -0.1(6) . . . . ?
C5' C4' C3' C2' -2.8(6) . . . . ?
I1' C4' C3' C2' 176.2(3) . . . . ?
C4' C3' C2' C7' 0.7(6) . . . . ?
C4' C3' C2' N1' 176.2(4) . . . . ?
C1' N1' C2' C7' -136.8(5) . . . . ?
C1' N1' C2' C3' 47.6(6) . . . . ?
C3' C2' C7' C6' 1.2(7) . . . . ?
N1' C2' C7' C6' -174.4(4) . . . . ?
C2' C7' C6' C5' -1.2(8) . . . . ?
C3' C4' C5' C6' 2.9(7) . . . . ?
I1' C4' C5' C6' -176.1(4) . . . . ?
C7' C6' C5' C4' -0.9(8) . . . . ?
C8' N2' C1' N1' -2.0(6) . . . . ?
C8' N2' C1' S1' 177.4(3) . . . . ?
C2' N1' C1' N2' -177.1(4) . . . . ?
C2' N1' C1' S1' 3.6(7) . . . . ?
C1' N2' C8' C9' 93.2(5) . . . . ?
C1' N2' C8' C13' -87.8(5) . . . . ?
C9' C8' C13' C12' -2.1(6) . . . . ?
N2' C8' C13' C12' 178.9(4) . . . . ?
C8' C13' C12' C11' 1.6(7) . . . . ?
C14' O1' C11' C12' -176.1(4) . . . . ?
C14' O1' C11' C10' 5.9(5) . . . . ?
C13' C12' C11' O1' -178.3(4) . . . . ?
C13' C12' C11' C10' -0.3(6) . . . . ?
O1' C11' C10' C9' 177.5(4) . . . . ?
C12' C11' C10' C9' -0.4(6) . . . . ?
C13' C8' C9' C10' 1.4(6) . . . . ?
N2' C8' C9' C10' -179.6(4) . . . . ?
C11' C10' C9' C8' -0.1(6) . . . . ?

_refine_diff_density_max         3.494
_refine_diff_density_min         -1.133
_refine_diff_density_rms         0.140

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_3iodo_nphenyl_3ome_lt_0m
_database_code_depnum_ccdc_archive 'CCDC 1483984'
_audit_update_record             
;
2016-07-21 deposited with the CCDC.
2016-08-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H13 I N2 O S'
_chemical_formula_sum            'C14 H13 I N2 O S'
_chemical_formula_weight         384.22

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'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.1518(6)
_cell_length_b                   18.2688(13)
_cell_length_c                   9.5334(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.6720(10)
_cell_angle_gamma                90
_cell_volume                     1416.83(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9987
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      31.51

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.801
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.260
_exptl_absorpt_coefficient_mu    2.401
_shelx_estimated_absorpt_T_min   0.425
_shelx_estimated_absorpt_T_max   0.574
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.425
_exptl_absorpt_correction_T_max  0.574
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22086
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.230
_diffrn_reflns_theta_max         31.753
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4463
_reflns_number_gt                4335
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0178P)²+1.7585P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4463
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0584
_refine_ls_wR_factor_gt          0.0580
_refine_ls_goodness_of_fit_ref   1.228
_refine_ls_restrained_S_all      1.228
_refine_ls_shift/su_max          0.003
_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_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 1.46291(2) 0.32718(2) 0.96768(2) 0.02160(4) Uani 1 1 d . . . . .
S1 S 0.82760(6) 0.43216(3) 1.06389(5) 0.01801(9) Uani 1 1 d . . . . .
O1 O 0.34197(17) 0.62490(8) 0.49180(14) 0.0200(3) Uani 1 1 d . . . . .
N1 N 0.8377(2) 0.40432(9) 0.78735(16) 0.0162(3) Uani 1 1 d . . . . .
H1 H 0.7882 0.4112 0.7036 0.019 Uiso 1 1 calc R U . . .
N2 N 0.6993(2) 0.50741(9) 0.84838(17) 0.0169(3) Uani 1 1 d . . . . .
H2 H 0.6478 0.5300 0.9143 0.020 Uiso 1 1 calc R U . . .
C1 C 0.7907(2) 0.44840(10) 0.89134(19) 0.0144(3) Uani 1 1 d . . . . .
C2 C 0.9584(2) 0.34814(10) 0.79852(19) 0.0147(3) Uani 1 1 d . . . . .
C3 C 1.1103(2) 0.36078(10) 0.87012(19) 0.0156(3) Uani 1 1 d . . . . .
H3 H 1.1318 0.4054 0.9190 0.019 Uiso 1 1 calc R U . . .
C4 C 1.2295(2) 0.30651(11) 0.86815(19) 0.0162(3) Uani 1 1 d . . . . .
C5 C 1.2025(2) 0.24115(11) 0.7955(2) 0.0197(4) Uani 1 1 d . . . . .
H5 H 1.2856 0.2047 0.7954 0.024 Uiso 1 1 calc R U . . .
C6 C 1.0509(3) 0.23047(11) 0.7230(2) 0.0215(4) Uani 1 1 d . . . . .
H6 H 1.0308 0.1865 0.6715 0.026 Uiso 1 1 calc R U . . .
C7 C 0.9284(2) 0.28330(10) 0.7248(2) 0.0183(3) Uani 1 1 d . . . . .
H7 H 0.8247 0.2752 0.6760 0.022 Uiso 1 1 calc R U . . .
C8 C 0.6757(2) 0.53764(10) 0.71071(19) 0.0147(3) Uani 1 1 d . . . . .
C9 C 0.5191(2) 0.56431(10) 0.67127(19) 0.0149(3) Uani 1 1 d . . . . .
H9 H 0.4326 0.5600 0.7329 0.018 Uiso 1 1 calc R U . . .
C10 C 0.4916(2) 0.59729(10) 0.54033(19) 0.0157(3) Uani 1 1 d . . . . .
C11 C 0.6178(2) 0.60340(11) 0.4491(2) 0.0197(4) Uani 1 1 d . . . . .
H11 H 0.5982 0.6257 0.3596 0.024 Uiso 1 1 calc R U . . .
C12 C 0.7721(2) 0.57645(12) 0.4907(2) 0.0218(4) Uani 1 1 d . . . . .
H12 H 0.8581 0.5800 0.4283 0.026 Uiso 1 1 calc R U . . .
C13 C 0.8038(2) 0.54432(11) 0.6218(2) 0.0197(4) Uani 1 1 d . . . . .
H13 H 0.9109 0.5272 0.6502 0.024 Uiso 1 1 calc R U . . .
C14 C 0.2220(2) 0.63279(15) 0.5894(2) 0.0277(5) Uani 1 1 d . . . . .
H14A H 0.1890 0.5844 0.6216 0.042 Uiso 1 1 calc R U . . .
H14B H 0.1261 0.6581 0.5450 0.042 Uiso 1 1 calc R U . . .
H14C H 0.2669 0.6615 0.6698 0.042 Uiso 1 1 calc R U . . .


_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 C4 2.1049(19) . ?
S1 C1 1.6797(18) . ?
O1 C10 1.373(2) . ?
O1 C14 1.400(2) . ?
N1 C1 1.352(2) . ?
N1 C2 1.421(2) . ?
N1 H1 0.8800 . ?
N2 C1 1.359(2) . ?
N2 C8 1.426(2) . ?
N2 H2 0.8800 . ?
C2 C7 1.391(3) . ?
C2 C3 1.395(3) . ?
C3 C4 1.389(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(3) . ?
C5 C6 1.391(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.390(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C13 1.392(3) . ?
C8 C9 1.395(2) . ?
C9 C10 1.391(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(3) . ?
C11 C12 1.385(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.390(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 C14 117.23(15) . . ?
C1 N1 C2 127.08(16) . . ?
C1 N1 H1 116.5 . . ?
C2 N1 H1 116.5 . . ?
C1 N2 C8 128.60(16) . . ?
C1 N2 H2 115.7 . . ?
C8 N2 H2 115.7 . . ?
N1 C1 N2 115.31(16) . . ?
N1 C1 S1 124.87(14) . . ?
N2 C1 S1 119.72(14) . . ?
C7 C2 C3 120.68(17) . . ?
C7 C2 N1 118.60(16) . . ?
C3 C2 N1 120.39(16) . . ?
C4 C3 C2 118.38(17) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 122.05(17) . . ?
C3 C4 I1 118.60(14) . . ?
C5 C4 I1 119.24(14) . . ?
C6 C5 C4 118.40(18) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C7 C6 C5 120.85(18) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C2 119.63(18) . . ?
C6 C7 H7 120.2 . . ?
C2 C7 H7 120.2 . . ?
C13 C8 C9 120.97(17) . . ?
C13 C8 N2 122.17(17) . . ?
C9 C8 N2 116.77(16) . . ?
C10 C9 C8 119.01(16) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
O1 C10 C9 123.37(17) . . ?
O1 C10 C11 115.82(16) . . ?
C9 C10 C11 120.80(17) . . ?
C12 C11 C10 119.05(17) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 121.40(18) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C8 118.75(18) . . ?
C12 C13 H13 120.6 . . ?
C8 C13 H13 120.6 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 N2 166.61(17) . . . . ?
C2 N1 C1 S1 -17.2(3) . . . . ?
C8 N2 C1 N1 -14.7(3) . . . . ?
C8 N2 C1 S1 168.87(15) . . . . ?
C1 N1 C2 C7 140.48(19) . . . . ?
C1 N1 C2 C3 -46.0(3) . . . . ?
C7 C2 C3 C4 -1.2(3) . . . . ?
N1 C2 C3 C4 -174.57(17) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C2 C3 C4 I1 177.09(13) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
I1 C4 C5 C6 -175.99(15) . . . . ?
C4 C5 C6 C7 -1.0(3) . . . . ?
C5 C6 C7 C2 0.9(3) . . . . ?
C3 C2 C7 C6 0.3(3) . . . . ?
N1 C2 C7 C6 173.74(18) . . . . ?
C1 N2 C8 C13 -41.2(3) . . . . ?
C1 N2 C8 C9 142.26(19) . . . . ?
C13 C8 C9 C10 0.6(3) . . . . ?
N2 C8 C9 C10 177.19(17) . . . . ?
C14 O1 C10 C9 12.8(3) . . . . ?
C14 O1 C10 C11 -167.85(19) . . . . ?
C8 C9 C10 O1 179.71(17) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
O1 C10 C11 C12 -179.73(18) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C10 C11 C12 C13 -0.7(3) . . . . ?
C11 C12 C13 C8 1.7(3) . . . . ?
C9 C8 C13 C12 -1.7(3) . . . . ?
N2 C8 C13 C12 -178.03(18) . . . . ?

_refine_diff_density_max         0.806
_refine_diff_density_min         -0.828
_refine_diff_density_rms         0.087

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_abc
_database_code_depnum_ccdc_archive 'CCDC 1483985'
_audit_update_record             
;
2016-06-07 deposited with the CCDC.
2016-08-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 I N3 O2 S'
_chemical_formula_sum            'C13 H10 I N3 O2 S'
_chemical_formula_weight         399.20

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'Pna2(1) '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   14.2167(19)
_cell_length_b                   14.5308(18)
_cell_length_c                   6.8955(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1424.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7445
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      30.33

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.861
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    2.399
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.4324
_exptl_absorpt_correction_T_max  0.6328
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15137
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2508
_reflns_number_gt                2415
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0314P)²+1.8463P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.12(3)
_refine_ls_number_reflns         2508
_refine_ls_number_parameters     181
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.0709
_refine_ls_wR_factor_gt          0.0701
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_restrained_S_all      1.159
_refine_ls_shift/su_max          0.001
_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
I1 I 0.91895(2) 0.427728(18) 0.58122(7) 0.04202(13) Uani 1 1 d . . .
S1 S 0.85949(8) 0.06528(7) 0.68599(17) 0.0216(2) Uani 1 1 d . . .
O1 O 0.7464(2) -0.4427(2) 0.6552(6) 0.0376(10) Uani 1 1 d . . .
O2 O 0.6245(2) -0.3553(2) 0.6596(5) 0.0289(8) Uani 1 1 d . . .
N1 N 1.0209(3) 0.0689(2) 0.4807(6) 0.0222(8) Uani 1 1 d . . .
H1 H 1.0606 0.0376 0.4084 0.027 Uiso 1 1 calc R . .
N2 N 0.9427(3) -0.0652(2) 0.4703(6) 0.0211(8) Uani 1 1 d . . .
H2 H 0.9875 -0.0790 0.3872 0.025 Uiso 1 1 calc R . .
N3 N 0.7087(3) -0.3671(3) 0.6391(5) 0.0230(10) Uani 1 1 d . . .
C1 C 0.9435(3) 0.0226(3) 0.5370(6) 0.0161(9) Uani 1 1 d . . .
C2 C 1.0474(3) 0.1613(3) 0.5214(6) 0.0181(10) Uani 1 1 d . . .
C3 C 0.9845(3) 0.2331(3) 0.5285(6) 0.0191(10) Uani 1 1 d . . .
H3 H 0.9191 0.2223 0.5130 0.023 Uiso 1 1 calc R . .
C4 C 1.0179(3) 0.3211(3) 0.5586(9) 0.0263(10) Uani 1 1 d . . .
C5 C 1.1127(3) 0.3389(3) 0.5807(9) 0.0286(9) Uani 1 1 d . . .
H5 H 1.1344 0.3998 0.6039 0.034 Uiso 1 1 calc R . .
C6 C 1.1752(3) 0.2668(3) 0.5685(10) 0.0252(9) Uani 1 1 d . . .
H6 H 1.2408 0.2784 0.5794 0.030 Uiso 1 1 calc R . .
C7 C 1.1436(3) 0.1776(3) 0.5405(6) 0.0226(11) Uani 1 1 d . . .
H7 H 1.1870 0.1280 0.5343 0.027 Uiso 1 1 calc R . .
C8 C 0.8797(3) -0.1382(3) 0.5155(6) 0.0177(9) Uani 1 1 d . . .
C9 C 0.9200(3) -0.2253(3) 0.5382(6) 0.0197(12) Uani 1 1 d . . .
H9 H 0.9861 -0.2327 0.5262 0.024 Uiso 1 1 calc R . .
C10 C 0.8642(3) -0.3002(3) 0.5777(9) 0.0234(9) Uani 1 1 d . . .
H10 H 0.8911 -0.3596 0.5932 0.028 Uiso 1 1 calc R . .
C11 C 0.7685(3) -0.2874(3) 0.5944(10) 0.0222(9) Uani 1 1 d . . .
C12 C 0.7275(3) -0.2020(3) 0.5643(9) 0.0245(10) Uani 1 1 d . . .
H12 H 0.6610 -0.1955 0.5709 0.029 Uiso 1 1 calc R . .
C13 C 0.7827(3) -0.1269(3) 0.5250(7) 0.0243(11) Uani 1 1 d . . .
H13 H 0.7552 -0.0681 0.5047 0.029 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C4 2.098(4) . ?
S1 C1 1.693(4) . ?
O1 N3 1.227(5) . ?
O2 N3 1.217(5) . ?
N1 C1 1.346(5) . ?
N1 C2 1.423(5) . ?
N1 H1 0.8800 . ?
N2 C1 1.356(5) . ?
N2 C8 1.423(5) . ?
N2 H2 0.8800 . ?
N3 C11 1.469(5) . ?
C2 C3 1.375(6) . ?
C2 C7 1.394(6) . ?
C3 C4 1.379(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(6) . ?
C5 C6 1.375(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(6) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C13 1.390(6) . ?
C8 C9 1.398(6) . ?
C9 C10 1.375(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.378(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.387(6) . ?
C12 C13 1.372(6) . ?
C12 H12 0.9500 . ?
C13 H13 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
C1 N1 C2 129.1(4) . . ?
C1 N1 H1 115.4 . . ?
C2 N1 H1 115.4 . . ?
C1 N2 C8 129.3(4) . . ?
C1 N2 H2 115.4 . . ?
C8 N2 H2 115.4 . . ?
O2 N3 O1 123.0(4) . . ?
O2 N3 C11 118.9(4) . . ?
O1 N3 C11 118.2(4) . . ?
N1 C1 N2 112.3(4) . . ?
N1 C1 S1 124.6(3) . . ?
N2 C1 S1 122.9(3) . . ?
C3 C2 C7 120.4(4) . . ?
C3 C2 N1 123.4(4) . . ?
C7 C2 N1 116.0(4) . . ?
C2 C3 C4 119.0(4) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 121.7(4) . . ?
C3 C4 I1 117.7(3) . . ?
C5 C4 I1 120.5(3) . . ?
C6 C5 C4 118.7(4) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C5 C6 C7 120.8(4) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C2 119.3(4) . . ?
C6 C7 H7 120.3 . . ?
C2 C7 H7 120.3 . . ?
C13 C8 C9 120.6(4) . . ?
C13 C8 N2 123.1(4) . . ?
C9 C8 N2 116.2(4) . . ?
C10 C9 C8 120.2(4) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 118.7(4) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
C10 C11 C12 121.6(4) . . ?
C10 C11 N3 118.9(4) . . ?
C12 C11 N3 119.5(4) . . ?
C13 C12 C11 120.0(4) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C8 118.9(4) . . ?
C12 C13 H13 120.6 . . ?
C8 C13 H13 120.6 . . ?

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
C2 N1 C1 N2 -179.7(4) . . . . ?
C2 N1 C1 S1 -3.4(7) . . . . ?
C8 N2 C1 N1 172.1(4) . . . . ?
C8 N2 C1 S1 -4.2(6) . . . . ?
C1 N1 C2 C3 -38.0(7) . . . . ?
C1 N1 C2 C7 146.6(4) . . . . ?
C7 C2 C3 C4 -1.3(6) . . . . ?
N1 C2 C3 C4 -176.5(4) . . . . ?
C2 C3 C4 C5 0.3(8) . . . . ?
C2 C3 C4 I1 -177.2(3) . . . . ?
C3 C4 C5 C6 1.3(9) . . . . ?
I1 C4 C5 C6 178.8(5) . . . . ?
C4 C5 C6 C7 -2.0(9) . . . . ?
C5 C6 C7 C2 1.1(8) . . . . ?
C3 C2 C7 C6 0.6(6) . . . . ?
N1 C2 C7 C6 176.1(4) . . . . ?
C1 N2 C8 C13 44.3(7) . . . . ?
C1 N2 C8 C9 -139.8(5) . . . . ?
C13 C8 C9 C10 -2.5(7) . . . . ?
N2 C8 C9 C10 -178.6(4) . . . . ?
C8 C9 C10 C11 0.0(8) . . . . ?
C9 C10 C11 C12 2.7(10) . . . . ?
C9 C10 C11 N3 -179.2(5) . . . . ?
O2 N3 C11 C10 177.8(5) . . . . ?
O1 N3 C11 C10 -1.7(8) . . . . ?
O2 N3 C11 C12 -4.1(8) . . . . ?
O1 N3 C11 C12 176.3(5) . . . . ?
C10 C11 C12 C13 -2.8(10) . . . . ?
N3 C11 C12 C13 179.1(5) . . . . ?
C11 C12 C13 C8 0.2(8) . . . . ?
C9 C8 C13 C12 2.4(7) . . . . ?
N2 C8 C13 C12 178.2(4) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.127
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.085
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 
'Dimethyl Formamide-Ethyl Acetate Mixture'
####################################################################### 
# 
# 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_RPG_09
_database_code_depnum_ccdc_archive 'CCDC 1483986'
_audit_update_record             
;
2016-07-21 deposited with the CCDC.
2016-08-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 I N2 S'
_chemical_formula_sum            'C13 H11 I N2 S'
_chemical_formula_weight         354.20

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'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.3895(12)
_cell_length_b                   5.4985(5)
_cell_length_c                   17.1612(15)
_cell_angle_alpha                90
_cell_angle_beta                 116.180(4)
_cell_angle_gamma                90
_cell_volume                     1303.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9835
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      38.22

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.805
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    2.596
_shelx_estimated_absorpt_T_min   0.375
_shelx_estimated_absorpt_T_max   0.612
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.375
_exptl_absorpt_correction_T_max  0.612
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33486
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.484
_diffrn_reflns_theta_max         40.969
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.696
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.696
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.696
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5966
_reflns_number_gt                5352
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0320P)²+3.8915P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5966
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1126
_refine_ls_wR_factor_gt          0.1094
_refine_ls_goodness_of_fit_ref   1.240
_refine_ls_restrained_S_all      1.240
_refine_ls_shift/su_max          0.001
_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_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 0.87286(2) 0.19264(5) 0.96840(2) 0.02867(7) Uani 1 1 d . . . . .
S1 S 0.97149(5) -0.07942(14) 0.61139(5) 0.02038(13) Uani 1 1 d . . . . .
N1 N 0.8680(2) 0.3207(5) 0.60343(16) 0.0215(4) Uani 1 1 d . . . . .
H1 H 0.8381 0.4526 0.5754 0.026 Uiso 1 1 calc R U . . .
N2 N 0.88557(18) 0.2252(5) 0.48068(15) 0.0202(4) Uani 1 1 d . . . . .
H2 H 0.9199 0.1493 0.4586 0.024 Uiso 1 1 calc R U . . .
C1 C 0.90379(18) 0.1658(5) 0.56246(16) 0.0159(4) Uani 1 1 d . . . . .
C2 C 0.87551(19) 0.2844(5) 0.68730(16) 0.0165(4) Uani 1 1 d . . . . .
C3 C 0.8371(2) 0.0786(5) 0.70672(18) 0.0192(5) Uani 1 1 d . . . . .
H3 H 0.8089 -0.0445 0.6641 0.023 Uiso 1 1 calc R U . . .
C4 C 0.8395(2) 0.0505(5) 0.78801(18) 0.0203(5) Uani 1 1 d . . . . .
H4 H 0.8139 -0.0921 0.8014 0.024 Uiso 1 1 calc R U . . .
C5 C 0.8796(2) 0.2329(5) 0.84946(17) 0.0187(5) Uani 1 1 d . . . . .
C6 C 0.9183(2) 0.4403(6) 0.83117(18) 0.0232(5) Uani 1 1 d . . . . .
H6 H 0.9459 0.5639 0.8737 0.028 Uiso 1 1 calc R U . . .
C7 C 0.9165(2) 0.4655(6) 0.74955(18) 0.0214(5) Uani 1 1 d . . . . .
H7 H 0.9433 0.6065 0.7365 0.026 Uiso 1 1 calc R U . . .
C8 C 0.81665(19) 0.3976(5) 0.42608(16) 0.0177(4) Uani 1 1 d . . . . .
C9 C 0.7185(2) 0.3666(6) 0.40275(19) 0.0227(5) Uani 1 1 d . . . . .
H9 H 0.6972 0.2336 0.4252 0.027 Uiso 1 1 calc R U . . .
C10 C 0.6519(2) 0.5309(7) 0.34649(19) 0.0272(6) Uani 1 1 d . . . . .
H10 H 0.5849 0.5108 0.3306 0.033 Uiso 1 1 calc R U . . .
C11 C 0.6830(3) 0.7249(6) 0.3132(2) 0.0283(6) Uani 1 1 d . . . . .
H11 H 0.6376 0.8393 0.2756 0.034 Uiso 1 1 calc R U . . .
C12 C 0.7806(3) 0.7505(6) 0.3352(2) 0.0268(6) Uani 1 1 d . . . . .
H12 H 0.8016 0.8805 0.3112 0.032 Uiso 1 1 calc R U . . .
C13 C 0.8481(2) 0.5880(6) 0.39197(19) 0.0239(5) Uani 1 1 d . . . . .
H13 H 0.9150 0.6073 0.4072 0.029 Uiso 1 1 calc R U . . .


_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 C5 2.101(3) . ?
S1 C1 1.684(3) . ?
N1 C1 1.366(3) . ?
N1 C2 1.406(3) . ?
N1 H1 0.8800 . ?
N2 C1 1.344(3) . ?
N2 C8 1.423(3) . ?
N2 H2 0.8800 . ?
C2 C3 1.384(4) . ?
C2 C7 1.392(4) . ?
C3 C4 1.388(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(4) . ?
C6 C7 1.396(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C13 1.387(4) . ?
C8 C9 1.392(4) . ?
C9 C10 1.387(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.391(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(4) . ?
C12 H12 0.9500 . ?
C13 H13 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
C1 N1 C2 124.7(2) . . ?
C1 N1 H1 117.7 . . ?
C2 N1 H1 117.7 . . ?
C1 N2 C8 126.9(2) . . ?
C1 N2 H2 116.5 . . ?
C8 N2 H2 116.5 . . ?
N2 C1 N1 116.1(2) . . ?
N2 C1 S1 120.9(2) . . ?
N1 C1 S1 123.0(2) . . ?
C3 C2 C7 119.8(2) . . ?
C3 C2 N1 120.8(3) . . ?
C7 C2 N1 119.3(3) . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 I1 121.2(2) . . ?
C4 C5 I1 117.8(2) . . ?
C5 C6 C7 119.3(3) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C2 C7 C6 120.1(3) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C13 C8 C9 120.5(3) . . ?
C13 C8 N2 118.9(3) . . ?
C9 C8 N2 120.4(3) . . ?
C10 C9 C8 119.6(3) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 120.2(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 119.6(3) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 120.7(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C8 C13 C12 119.3(3) . . ?
C8 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N2 C1 N1 -14.9(4) . . . . ?
C8 N2 C1 S1 167.9(2) . . . . ?
C2 N1 C1 N2 176.9(3) . . . . ?
C2 N1 C1 S1 -5.9(4) . . . . ?
C1 N1 C2 C3 -58.9(4) . . . . ?
C1 N1 C2 C7 125.3(3) . . . . ?
C7 C2 C3 C4 -0.3(4) . . . . ?
N1 C2 C3 C4 -176.1(3) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
C3 C4 C5 I1 175.9(2) . . . . ?
C4 C5 C6 C7 0.2(5) . . . . ?
I1 C5 C6 C7 -176.5(2) . . . . ?
C3 C2 C7 C6 -0.4(4) . . . . ?
N1 C2 C7 C6 175.5(3) . . . . ?
C5 C6 C7 C2 0.4(5) . . . . ?
C1 N2 C8 C13 123.1(3) . . . . ?
C1 N2 C8 C9 -61.0(4) . . . . ?
C13 C8 C9 C10 -1.5(4) . . . . ?
N2 C8 C9 C10 -177.3(3) . . . . ?
C8 C9 C10 C11 0.3(5) . . . . ?
C9 C10 C11 C12 1.3(5) . . . . ?
C10 C11 C12 C13 -1.7(5) . . . . ?
C9 C8 C13 C12 1.1(4) . . . . ?
N2 C8 C13 C12 176.9(3) . . . . ?
C11 C12 C13 C8 0.5(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 S1 0.88 2.48 3.323(2) 160.6 3_756
C7 H7 S1 0.95 2.93 3.791(3) 150.8 1_565
C3 H3 I1 0.95 3.08 3.925(3) 149.5 2_646

_refine_diff_density_max         2.651
_refine_diff_density_min         -1.510
_refine_diff_density_rms         0.155

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_azx
_database_code_depnum_ccdc_archive 'CCDC 1483987'
_audit_update_record             
;
2016-06-07 deposited with the CCDC.
2016-08-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 I N2 O'
_chemical_formula_sum            'C13 H11 I N2 O'
_chemical_formula_weight         338.14

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   26.1800(17)
_cell_length_b                   4.6273(3)
_cell_length_c                   9.9779(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.646(3)
_cell_angle_gamma                90.00
_cell_volume                     1208.25(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4903
_cell_measurement_theta_min      3.89
_cell_measurement_theta_max      28.72

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.859
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    2.635
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.4506
_exptl_absorpt_correction_T_max  0.6208
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6668
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2056
_reflns_number_gt                1829
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0875P)²+0.1074P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2056
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.1324
_refine_ls_wR_factor_gt          0.0853
_refine_ls_goodness_of_fit_ref   1.187
_refine_ls_restrained_S_all      1.187
_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
I1 I 0.049609(10) 0.26831(7) 1.16736(3) 0.0330(2) Uani 1 1 d . . .
O1 O 0.27828(12) 0.3313(7) 0.8227(3) 0.0281(7) Uani 1 1 d . . .
N2 N 0.31671(16) 0.7530(7) 0.7676(4) 0.0271(10) Uani 1 1 d . . .
H2 H 0.3155 0.9428 0.7718 0.032 Uiso 1 1 calc R . .
N1 N 0.24212(16) 0.7599(7) 0.8790(5) 0.0247(9) Uani 1 1 d . . .
H1 H 0.2449 0.9492 0.8748 0.030 Uiso 1 1 calc R . .
C1 C 0.27887(13) 0.5990(10) 0.8238(3) 0.0203(8) Uani 1 1 d . . .
C2 C 0.19911(14) 0.6423(10) 0.9436(4) 0.0201(8) Uani 1 1 d . . .
C3 C 0.20477(13) 0.4328(10) 1.0433(3) 0.0239(9) Uani 1 1 d . . .
H3 H 0.2379 0.3643 1.0686 0.029 Uiso 1 1 calc R . .
C4 C 0.16197(17) 0.3233(10) 1.1062(4) 0.0253(9) Uani 1 1 d . . .
H4 H 0.1657 0.1773 1.1727 0.030 Uiso 1 1 calc R . .
C5 C 0.11399(13) 0.4291(10) 1.0710(3) 0.0229(9) Uani 1 1 d . . .
C6 C 0.10801(14) 0.6407(11) 0.9737(4) 0.0269(9) Uani 1 1 d . . .
H6 H 0.0750 0.7143 0.9509 0.032 Uiso 1 1 calc R . .
C7 C 0.1507(2) 0.7442(8) 0.9098(5) 0.0269(12) Uani 1 1 d . . .
H7 H 0.1467 0.8869 0.8419 0.032 Uiso 1 1 calc R . .
C8 C 0.35844(13) 0.6215(10) 0.7020(3) 0.0214(8) Uani 1 1 d . . .
C13 C 0.40820(19) 0.6950(10) 0.7387(5) 0.0294(11) Uani 1 1 d . . .
H13 H 0.4146 0.8321 0.8081 0.035 Uiso 1 1 calc R . .
C12 C 0.44863(14) 0.5684(11) 0.6741(4) 0.0335(10) Uani 1 1 d . . .
H12 H 0.4826 0.6219 0.6988 0.040 Uiso 1 1 calc R . .
C11 C 0.44028(16) 0.3660(12) 0.5744(4) 0.0321(10) Uani 1 1 d . . .
H11 H 0.4681 0.2773 0.5314 0.038 Uiso 1 1 calc R . .
C10 C 0.3900(2) 0.2944(10) 0.5382(5) 0.0332(12) Uani 1 1 d . . .
H10 H 0.3836 0.1550 0.4699 0.040 Uiso 1 1 calc R . .
C9 C 0.34961(14) 0.4226(10) 0.5999(3) 0.0271(9) Uani 1 1 d . . .
H9 H 0.3156 0.3750 0.5727 0.033 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C5 2.101(4) . ?
O1 C1 1.239(5) . ?
N2 C1 1.355(6) . ?
N2 C8 1.426(6) . ?
N1 C1 1.347(6) . ?
N1 C2 1.422(6) . ?
C2 C7 1.384(6) . ?
C2 C3 1.394(6) . ?
C3 C4 1.395(6) . ?
C4 C5 1.384(6) . ?
C5 C6 1.384(6) . ?
C6 C7 1.388(7) . ?
C8 C13 1.385(6) . ?
C8 C9 1.387(6) . ?
C13 C12 1.385(7) . ?
C12 C11 1.379(7) . ?
C11 C10 1.396(7) . ?
C10 C9 1.373(7) . ?

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
C1 N2 C8 123.0(4) . . ?
C1 N1 C2 123.9(3) . . ?
O1 C1 N1 123.2(4) . . ?
O1 C1 N2 122.1(4) . . ?
N1 C1 N2 114.7(4) . . ?
C7 C2 C3 119.3(4) . . ?
C7 C2 N1 119.3(4) . . ?
C3 C2 N1 121.4(3) . . ?
C2 C3 C4 120.2(3) . . ?
C5 C4 C3 119.5(4) . . ?
C4 C5 C6 120.8(4) . . ?
C4 C5 I1 119.5(3) . . ?
C6 C5 I1 119.7(3) . . ?
C5 C6 C7 119.3(4) . . ?
C2 C7 C6 120.9(4) . . ?
C13 C8 C9 119.5(4) . . ?
C13 C8 N2 120.1(4) . . ?
C9 C8 N2 120.4(3) . . ?
C12 C13 C8 119.9(4) . . ?
C11 C12 C13 121.0(4) . . ?
C12 C11 C10 118.5(4) . . ?
C9 C10 C11 120.9(4) . . ?
C10 C9 C8 120.1(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
C2 N1 C1 O1 1.0(6) . . . . ?
C2 N1 C1 N2 -179.7(4) . . . . ?
C8 N2 C1 O1 0.6(6) . . . . ?
C8 N2 C1 N1 -178.7(4) . . . . ?
C1 N1 C2 C7 -131.0(5) . . . . ?
C1 N1 C2 C3 51.0(6) . . . . ?
C7 C2 C3 C4 1.3(6) . . . . ?
N1 C2 C3 C4 179.3(4) . . . . ?
C2 C3 C4 C5 -1.5(6) . . . . ?
C3 C4 C5 C6 0.4(6) . . . . ?
C3 C4 C5 I1 -179.2(3) . . . . ?
C4 C5 C6 C7 0.9(6) . . . . ?
I1 C5 C6 C7 -179.5(3) . . . . ?
C3 C2 C7 C6 0.0(7) . . . . ?
N1 C2 C7 C6 -178.0(4) . . . . ?
C5 C6 C7 C2 -1.1(7) . . . . ?
C1 N2 C8 C13 -127.3(5) . . . . ?
C1 N2 C8 C9 53.6(6) . . . . ?
C9 C8 C13 C12 -0.4(7) . . . . ?
N2 C8 C13 C12 -179.5(4) . . . . ?
C8 C13 C12 C11 -0.9(7) . . . . ?
C13 C12 C11 C10 1.1(7) . . . . ?
C12 C11 C10 C9 0.1(7) . . . . ?
C11 C10 C9 C8 -1.5(7) . . . . ?
C13 C8 C9 C10 1.6(6) . . . . ?
N2 C8 C9 C10 -179.3(4) . . . . ?

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 O1 0.88 2.05 2.869(5) 155.3 1_565
N2 H2 O1 0.88 2.11 2.917(5) 151.4 1_565

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         1.193
_refine_diff_density_min         -1.060
_refine_diff_density_rms         0.255
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 
'Dimethyl Formamide-Ethyl Acetate Mixture'
####################################################################### 
# 
# 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_ABC
_database_code_depnum_ccdc_archive 'CCDC 1484013'
_audit_update_record             
;
2016-07-21 deposited with the CCDC.
2016-08-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 I N2 O'
_chemical_formula_sum            'C13 H11 I N2 O'
_chemical_formula_weight         338.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   27.253(5)
_cell_length_b                   4.6408(9)
_cell_length_c                   9.8532(18)
_cell_angle_alpha                90
_cell_angle_beta                 91.991(6)
_cell_angle_gamma                90
_cell_volume                     1245.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7496
_cell_measurement_theta_min      3.25
_cell_measurement_theta_max      68.24

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.803
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    20.081
_shelx_estimated_absorpt_T_min   0.052
_shelx_estimated_absorpt_T_max   0.086
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.052
_exptl_absorpt_correction_T_max  0.086
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   Cu
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11283
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.871
_diffrn_reflns_theta_max         68.388
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 0.942
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.942
_reflns_number_total             2158
_reflns_number_gt                1859
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0839P)²+3.3102P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2158
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0570
_refine_ls_wR_factor_ref         0.1728
_refine_ls_wR_factor_gt          0.1608
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.150
_refine_ls_shift/su_max          0.001
_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_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 0.95164(2) 0.73464(12) 0.65377(7) 0.0725(3) Uani 1 1 d . . . . .
O1 O 0.71779(16) 0.3178(8) 0.6875(5) 0.0417(10) Uani 1 1 d . . . . .
N1 N 0.7528(2) 0.7427(9) 0.6310(6) 0.0417(13) Uani 1 1 d . . . . .
H1 H 0.7494 0.9313 0.6295 0.050 Uiso 1 1 calc R U . . .
N2 N 0.6801(2) 0.7388(10) 0.7370(6) 0.0432(13) Uani 1 1 d . . . . .
H2 H 0.6812 0.9276 0.7297 0.052 Uiso 1 1 calc R U . . .
C1 C 0.71680(18) 0.5809(12) 0.6857(6) 0.0309(11) Uani 1 1 d . . . . .
C2 C 0.79571(19) 0.6194(12) 0.5759(6) 0.0336(12) Uani 1 1 d . . . . .
C3 C 0.8415(2) 0.7081(13) 0.6271(7) 0.0397(13) Uani 1 1 d . . . . .
H3 H 0.8440 0.8481 0.6973 0.048 Uiso 1 1 calc R U . . .
C4 C 0.88329(19) 0.5901(14) 0.5744(6) 0.0413(14) Uani 1 1 d . . . . .
C5 C 0.8810(2) 0.3880(15) 0.4742(7) 0.0490(16) Uani 1 1 d . . . . .
H5 H 0.9102 0.3084 0.4396 0.059 Uiso 1 1 calc R U . . .
C6 C 0.8349(3) 0.2998(14) 0.4230(7) 0.0477(16) Uani 1 1 d . . . . .
H6 H 0.8325 0.1592 0.3531 0.057 Uiso 1 1 calc R U . . .
C7 C 0.7929(2) 0.4160(13) 0.4738(6) 0.0407(13) Uani 1 1 d . . . . .
H7 H 0.7617 0.3558 0.4383 0.049 Uiso 1 1 calc R U . . .
C8 C 0.63962(19) 0.6117(12) 0.8022(6) 0.0346(12) Uani 1 1 d . . . . .
C9 C 0.5922(2) 0.6929(15) 0.7644(7) 0.0472(15) Uani 1 1 d . . . . .
H9 H 0.5867 0.8321 0.6948 0.057 Uiso 1 1 calc R U . . .
C10 C 0.5527(2) 0.5716(18) 0.8278(8) 0.0564(18) Uani 1 1 d . . . . .
H10 H 0.5203 0.6299 0.8021 0.068 Uiso 1 1 calc R U . . .
C11 C 0.5598(2) 0.3687(18) 0.9271(8) 0.0570(19) Uani 1 1 d . . . . .
H11 H 0.5326 0.2840 0.9697 0.068 Uiso 1 1 calc R U . . .
C12 C 0.6067(3) 0.2895(15) 0.9642(8) 0.0564(19) Uani 1 1 d . . . . .
H12 H 0.6119 0.1477 1.0327 0.068 Uiso 1 1 calc R U . . .
C13 C 0.6466(2) 0.4132(14) 0.9034(6) 0.0431(14) Uani 1 1 d . . . . .
H13 H 0.6790 0.3598 0.9321 0.052 Uiso 1 1 calc R U . . .


_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 C4 2.105(6) . ?
O1 C1 1.222(7) . ?
N1 C1 1.361(7) . ?
N1 C2 1.427(7) . ?
N1 H1 0.8800 . ?
N2 C1 1.352(7) . ?
N2 C8 1.423(7) . ?
N2 H2 0.8800 . ?
C2 C7 1.380(9) . ?
C2 C3 1.393(9) . ?
C3 C4 1.380(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.362(10) . ?
C5 C6 1.400(11) . ?
C5 H5 0.9500 . ?
C6 C7 1.374(9) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C13 1.366(9) . ?
C8 C9 1.386(9) . ?
C9 C10 1.382(10) . ?
C9 H9 0.9500 . ?
C10 C11 1.367(11) . ?
C10 H10 0.9500 . ?
C11 C12 1.367(12) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(10) . ?
C12 H12 0.9500 . ?
C13 H13 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
C1 N1 C2 122.8(5) . . ?
C1 N1 H1 118.6 . . ?
C2 N1 H1 118.6 . . ?
C1 N2 C8 122.6(5) . . ?
C1 N2 H2 118.7 . . ?
C8 N2 H2 118.7 . . ?
O1 C1 N2 123.5(5) . . ?
O1 C1 N1 122.8(5) . . ?
N2 C1 N1 113.7(5) . . ?
C7 C2 C3 119.5(5) . . ?
C7 C2 N1 121.8(5) . . ?
C3 C2 N1 118.7(5) . . ?
C4 C3 C2 119.2(6) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 121.9(6) . . ?
C5 C4 I1 120.4(4) . . ?
C3 C4 I1 117.7(5) . . ?
C4 C5 C6 118.7(5) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C7 C6 C5 120.2(6) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C2 120.6(6) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
C13 C8 C9 119.0(5) . . ?
C13 C8 N2 121.2(5) . . ?
C9 C8 N2 119.8(6) . . ?
C10 C9 C8 120.1(7) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 120.7(6) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 119.0(6) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C13 120.9(7) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C8 C13 C12 120.2(6) . . ?
C8 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?

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
C8 N2 C1 O1 2.1(10) . . . . ?
C8 N2 C1 N1 -178.2(6) . . . . ?
C2 N1 C1 O1 -2.6(10) . . . . ?
C2 N1 C1 N2 177.7(6) . . . . ?
C1 N1 C2 C7 56.4(9) . . . . ?
C1 N1 C2 C3 -123.6(7) . . . . ?
C7 C2 C3 C4 0.0(9) . . . . ?
N1 C2 C3 C4 180.0(5) . . . . ?
C2 C3 C4 C5 -0.3(9) . . . . ?
C2 C3 C4 I1 179.4(4) . . . . ?
C3 C4 C5 C6 0.4(10) . . . . ?
I1 C4 C5 C6 -179.3(5) . . . . ?
C4 C5 C6 C7 -0.1(10) . . . . ?
C5 C6 C7 C2 -0.3(10) . . . . ?
C3 C2 C7 C6 0.3(9) . . . . ?
N1 C2 C7 C6 -179.7(6) . . . . ?
C1 N2 C8 C13 50.4(9) . . . . ?
C1 N2 C8 C9 -130.6(7) . . . . ?
C13 C8 C9 C10 -0.6(10) . . . . ?
N2 C8 C9 C10 -179.6(6) . . . . ?
C8 C9 C10 C11 -0.7(11) . . . . ?
C9 C10 C11 C12 0.8(12) . . . . ?
C10 C11 C12 C13 0.4(11) . . . . ?
C9 C8 C13 C12 1.8(10) . . . . ?
N2 C8 C13 C12 -179.2(6) . . . . ?
C11 C12 C13 C8 -1.8(11) . . . . ?

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
N2 H2 O1 0.88 2.12 2.924(6) 152.5 1_565
N1 H1 O1 0.88 2.08 2.895(6) 153.9 1_565
N2 H2 O1 0.88 2.12 2.924(6) 152.5 1_565
N1 H1 O1 0.88 2.08 2.895(6) 153.9 1_565
N2 H2 O1 0.88 2.12 2.924(6) 152.5 1_565
N1 H1 O1 0.88 2.08 2.895(6) 153.9 1_565
N2 H2 O1 0.88 2.12 2.924(6) 152.5 1_565
N1 H1 O1 0.88 2.08 2.895(6) 153.9 1_565
N2 H2 O1 0.88 2.12 2.924(6) 152.5 1_565
N1 H1 O1 0.88 2.08 2.895(6) 153.9 1_565
N1 H1 O1 0.88 2.08 2.895(6) 153.9 1_565
N2 H2 O1 0.88 2.12 2.924(6) 152.5 1_565
N2 H2 O1 0.88 2.12 2.924(6) 152.5 1_565
N1 H1 O1 0.88 2.08 2.895(6) 153.9 1_565
N2 H2 O1 0.88 2.12 2.924(6) 152.5 1_565
N1 H1 O1 0.88 2.08 2.895(6) 153.9 1_565
N2 H2 O1 0.88 2.12 2.924(6) 152.5 1_565
N1 H1 O1 0.88 2.08 2.895(6) 153.9 1_565
N2 H2 O1 0.88 2.12 2.924(6) 152.5 1_565
N1 H1 O1 0.88 2.08 2.895(6) 153.9 1_565
N1 H1 O1 0.88 2.08 2.895(6) 153.9 1_565
N2 H2 O1 0.88 2.12 2.924(6) 152.5 1_565
N1 H1 O1 0.88 2.08 2.895(6) 153.9 1_565
N2 H2 O1 0.88 2.12 2.924(6) 152.5 1_565
N1 H1 O1 0.88 2.08 2.895(6) 153.9 1_565
N2 H2 O1 0.88 2.12 2.924(6) 152.5 1_565
N1 H1 O1 0.88 2.08 2.895(6) 153.9 1_565
N2 H2 O1 0.88 2.12 2.924(6) 152.5 1_565
N1 H1 O1 0.88 2.08 2.895(6) 153.9 1_565
N2 H2 O1 0.88 2.12 2.924(6) 152.5 1_565
N2 H2 O1 0.88 2.12 2.924(6) 152.5 1_565
N1 H1 O1 0.88 2.08 2.895(6) 153.9 1_565
N1 H1 O1 0.88 2.08 2.895(6) 153.9 1_565
N2 H2 O1 0.88 2.12 2.924(6) 152.5 1_565
N1 H1 O1 0.88 2.08 2.895(6) 153.9 1_565
N2 H2 O1 0.88 2.12 2.924(6) 152.5 1_565
N1 H1 O1 0.88 2.08 2.895(6) 153.9 1_565
N2 H2 O1 0.88 2.12 2.924(6) 152.5 1_565
N1 H1 O1 0.88 2.08 2.895(6) 153.9 1_565
N2 H2 O1 0.88 2.12 2.924(6) 152.5 1_565
N1 H1 O1 0.88 2.08 2.895(6) 153.9 1_565
N2 H2 O1 0.88 2.12 2.924(6) 152.5 1_565

_refine_diff_density_max         0.659
_refine_diff_density_min         -0.744
_refine_diff_density_rms         0.137

_shelxl_version_number           2013-3

