# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_2d
_database_code_depnum_ccdc_archive 'CCDC 2255940'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        4-Piperidinopyridine
_chemical_name_common            OID-113
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H14 N2'
_chemical_formula_sum            'C10 H14 N2'
_chemical_formula_weight         162.23

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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           122
_space_group_name_H-M_alt        'I -4 2 d'
_space_group_name_Hall           'I -4 2bw'

_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, z'
'y, -x, -z'
'-y, x, -z'
'-x+1/2, y, -z+3/4'
'x+1/2, -y, -z+3/4'
'-y+1/2, -x, z+3/4'
'y+1/2, x, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'
'-x+1, y+1/2, -z+5/4'
'x+1, -y+1/2, -z+5/4'
'-y+1, -x+1/2, z+5/4'
'y+1, x+1/2, z+5/4'

_cell_length_a                   12.6737(7)
_cell_length_b                   12.6737(7)
_cell_length_c                   11.6271(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1867.6(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1225
_cell_measurement_theta_min      3.9840
_cell_measurement_theta_max      22.5340

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.070
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.61460
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.785
_oxdiff_exptl_absorpt_empirical_full_max 1.243
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3863
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.215
_diffrn_reflns_theta_max         26.247
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             931
_reflns_number_gt                793
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_max     0.980
_reflns_Friedel_fraction_full    0.986

_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       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0344P)²+0.4920P] 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-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0054(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 254 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         931
_refine_ls_number_parameters     76
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1017
_refine_ls_wR_factor_gt          0.0907
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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
N1 N 0.0148(2) 0.250000 0.125000 0.0311(8) Uani 1 2 d S T P . .
N2 N 0.3483(2) 0.250000 0.125000 0.0342(8) Uani 1 2 d S T P . .
C1 C 0.07268(18) 0.3025(2) 0.2034(2) 0.0287(6) Uani 1 1 d . . . . .
H1 H 0.035621 0.340729 0.260911 0.034 Uiso 1 1 calc R U . . .
C2 C 0.18054(19) 0.30519(19) 0.2070(2) 0.0272(6) Uani 1 1 d . . . . .
H2 H 0.215348 0.344580 0.265287 0.033 Uiso 1 1 calc R U . . .
C3 C 0.2397(3) 0.250000 0.125000 0.0254(8) Uani 1 2 d S T P . .
C4A C 0.4076(10) 0.3087(9) 0.2151(8) 0.035(2) Uani 0.5 1 d . . P . .
H4A1 H 0.419673 0.261870 0.281983 0.042 Uiso 0.5 1 calc R U P . .
H4A2 H 0.364990 0.369548 0.241405 0.042 Uiso 0.5 1 calc R U P . .
C4B C 0.4079(11) 0.3369(9) 0.1727(9) 0.040(2) Uani 0.5 1 d . . P . .
H4B1 H 0.367064 0.369571 0.235960 0.048 Uiso 0.5 1 calc R U P . .
H4B2 H 0.419021 0.391006 0.112595 0.048 Uiso 0.5 1 calc R U P . .
C5A C 0.5115(7) 0.3474(7) 0.1707(7) 0.046(2) Uani 0.5 1 d . . P . .
H5A1 H 0.550965 0.383112 0.233095 0.056 Uiso 0.5 1 calc R U P . .
H5A2 H 0.500121 0.398735 0.107785 0.056 Uiso 0.5 1 calc R U P . .
C5B C 0.5137(6) 0.3007(7) 0.2182(7) 0.048(2) Uani 0.5 1 d . . P . .
H5B1 H 0.552955 0.362009 0.249197 0.057 Uiso 0.5 1 calc R U P . .
H5B2 H 0.502872 0.249759 0.281681 0.057 Uiso 0.5 1 calc R U P . .
C6A C 0.5765(3) 0.250000 0.125000 0.0560(13) Uani 0.5 2 d S T P . .
H6A1 H 0.645601 0.273644 0.094798 0.067 Uiso 0.25 1 calc R U P . .
H6A2 H 0.589157 0.199114 0.188110 0.067 Uiso 0.25 1 calc R U P . .
C6B C 0.5765(3) 0.250000 0.125000 0.0560(13) Uani 0.5 2 d S T P . .
H6B1 H 0.645601 0.226356 0.155203 0.067 Uiso 0.25 1 calc R U P . .
H6B2 H 0.589157 0.300886 0.061890 0.067 Uiso 0.25 1 calc R U P . .


_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
N1 C1 1.346(3) 14_454 ?
N1 C1 1.346(3) . ?
N2 C3 1.376(4) . ?
N2 C4B 1.446(13) . ?
N2 C4B 1.446(13) 14_454 ?
N2 C4A 1.489(11) . ?
N2 C4A 1.489(11) 14_454 ?
C1 C2 1.368(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.401(3) . ?
C2 H2 0.9500 . ?
C4A C5A 1.497(15) . ?
C4A H4A1 0.9900 . ?
C4A H4A2 0.9900 . ?
C4B C5B 1.513(15) . ?
C4B H4B1 0.9900 . ?
C4B H4B2 0.9900 . ?
C5A C6A 1.576(9) . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C5B H5B1 0.9900 . ?
C5B H5B2 0.9900 . ?
C6A H6A1 0.9900 . ?
C6A H6A2 0.9900 . ?
C6A H6A1 0.9900 14_454 ?
C6A H6A2 0.9900 14_454 ?

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 C1 114.0(3) 14_454 . ?
C3 N2 C4B 121.5(5) . . ?
C3 N2 C4B 121.5(5) . 14_454 ?
C4B N2 C4B 117.0(11) . 14_454 ?
C3 N2 C4A 120.3(5) . . ?
C4B N2 C4A 112.8(4) 14_454 . ?
C3 N2 C4A 120.3(5) . 14_454 ?
C4B N2 C4A 112.8(4) . 14_454 ?
C4A N2 C4A 119.4(10) . 14_454 ?
N1 C1 C2 125.3(3) . . ?
N1 C1 H1 117.4 . . ?
C2 C1 H1 117.4 . . ?
C1 C2 C3 120.1(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
N2 C3 C2 122.39(15) . . ?
N2 C3 C2 122.39(15) . 14_454 ?
C2 C3 C2 115.2(3) . 14_454 ?
N2 C4A C5A 111.4(7) . . ?
N2 C4A H4A1 109.3 . . ?
C5A C4A H4A1 109.3 . . ?
N2 C4A H4A2 109.3 . . ?
C5A C4A H4A2 109.3 . . ?
H4A1 C4A H4A2 108.0 . . ?
N2 C4B C5B 111.5(8) . . ?
N2 C4B H4B1 109.3 . . ?
C5B C4B H4B1 109.3 . . ?
N2 C4B H4B2 109.3 . . ?
C5B C4B H4B2 109.3 . . ?
H4B1 C4B H4B2 108.0 . . ?
C4A C5A C6A 108.6(7) . . ?
C4A C5A H5A1 110.0 . . ?
C6A C5A H5A1 110.0 . . ?
C4A C5A H5A2 110.0 . . ?
C6A C5A H5A2 110.0 . . ?
H5A1 C5A H5A2 108.3 . . ?
C4B C5B H5B1 109.6 . . ?
C4B C5B H5B2 109.6 . . ?
H5B1 C5B H5B2 108.1 . . ?
C5B C6A C5A 107.7(4) 14_454 . ?
C5B C6A H6A1 110.2 14_454 . ?
C5A C6A H6A1 110.2 . . ?
C5B C6A H6A2 110.2 14_454 . ?
C5A C6A H6A2 110.2 . . ?
H6A1 C6A H6A2 108.5 . . ?
C5B C6A H6A1 126.8(4) 14_454 14_454 ?
C5A C6A H6A1 125.4(3) . 14_454 ?
H6A1 C6A H6A1 55.6 . 14_454 ?
H6A2 C6A H6A1 52.9 . 14_454 ?
C5B C6A H6A2 80.1(3) 14_454 14_454 ?
C5A C6A H6A2 79.9(3) . 14_454 ?
H6A1 C6A H6A2 52.9 . 14_454 ?
H6A2 C6A H6A2 161.4 . 14_454 ?
H6A1 C6A H6A2 108.5 14_454 14_454 ?

_refine_diff_density_max         0.110
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.031



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

data_3a
_database_code_depnum_ccdc_archive 'CCDC 2255941'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        THY-518
_chemical_name_common            (NISac+4-Ethylpyridine)+DMAP
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 I N3 O3 S'
_chemical_formula_sum            'C14 H14 I N3 O3 S'
_chemical_formula_weight         431.24

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/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                   9.0129(2)
_cell_length_b                   12.312(4)
_cell_length_c                   14.5193(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.6110(10)
_cell_angle_gamma                90
_cell_volume                     1578.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    4074
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      30.508

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    2.177
_shelx_estimated_absorpt_T_min   0.581
_shelx_estimated_absorpt_T_max   0.765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6226
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12440
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.188
_diffrn_reflns_theta_max         30.859
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4891
_reflns_number_gt                3756
_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0086P)²+1.8201P] 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         4891
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0710
_refine_ls_wR_factor_gt          0.0659
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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 0.37002(2) 0.36081(2) 0.38521(2) 0.03100(6) Uani 1 1 d . . . . .
S1 S 0.49093(8) 0.46644(5) 0.19999(5) 0.02767(14) Uani 1 1 d . . . . .
O1 O 0.4968(2) 0.57411(15) 0.23846(16) 0.0387(5) Uani 1 1 d . . . . .
O2 O 0.3536(2) 0.43877(16) 0.13545(15) 0.0350(5) Uani 1 1 d . . . . .
O3 O 0.7070(3) 0.24290(16) 0.33612(15) 0.0404(5) Uani 1 1 d . . . . .
N1 N 0.5313(3) 0.37613(18) 0.28421(17) 0.0323(5) Uani 1 1 d . . . . .
N2 N 0.2052(3) 0.35851(18) 0.48078(17) 0.0317(5) Uani 1 1 d . . . . .
N3 N -0.1110(3) 0.37363(19) 0.65321(19) 0.0343(5) Uani 1 1 d . . . . .
C1 C 0.6507(3) 0.4378(2) 0.1522(2) 0.0262(5) Uani 1 1 d . . . . .
C2 C 0.6953(3) 0.4858(2) 0.0760(2) 0.0325(6) Uani 1 1 d . . . . .
H2 H 0.640290 0.544616 0.043079 0.039 Uiso 1 1 calc R U . . .
C3 C 0.8235(3) 0.4445(2) 0.0498(2) 0.0359(7) Uani 1 1 d . . . . .
H3 H 0.856842 0.474717 -0.002781 0.043 Uiso 1 1 calc R U . . .
C4 C 0.9039(4) 0.3597(2) 0.0991(2) 0.0389(7) Uani 1 1 d . . . . .
H4 H 0.991893 0.333154 0.079957 0.047 Uiso 1 1 calc R U . . .
C5 C 0.8588(3) 0.3125(2) 0.1762(2) 0.0341(6) Uani 1 1 d . . . . .
H5 H 0.914620 0.254357 0.209645 0.041 Uiso 1 1 calc R U . . .
C6 C 0.7299(3) 0.3529(2) 0.2025(2) 0.0283(6) Uani 1 1 d . . . . .
C7 C 0.6587(3) 0.3154(2) 0.2812(2) 0.0303(6) Uani 1 1 d . . . . .
C8 C 0.0720(3) 0.3043(2) 0.4582(2) 0.0340(6) Uani 1 1 d . . . . .
H8 H 0.051917 0.262471 0.402113 0.041 Uiso 1 1 calc R U . . .
C9 C -0.0343(3) 0.3073(2) 0.5129(2) 0.0324(6) Uani 1 1 d . . . . .
H9 H -0.126427 0.268331 0.494081 0.039 Uiso 1 1 calc R U . . .
C10 C -0.0089(3) 0.3680(2) 0.5975(2) 0.0292(6) Uani 1 1 d . . . . .
C11 C 0.1322(3) 0.4229(2) 0.6194(2) 0.0341(6) Uani 1 1 d . . . . .
H11 H 0.157147 0.464530 0.675472 0.041 Uiso 1 1 calc R U . . .
C12 C 0.2316(3) 0.4165(2) 0.5609(2) 0.0339(6) Uani 1 1 d . . . . .
H12 H 0.324563 0.454995 0.577241 0.041 Uiso 1 1 calc R U . . .
C13 C -0.2581(3) 0.3209(2) 0.6265(3) 0.0412(8) Uani 1 1 d . . . . .
H13A H -0.309284 0.347029 0.564454 0.062 Uiso 1 1 calc R U . . .
H13B H -0.319923 0.338163 0.672899 0.062 Uiso 1 1 calc R U . . .
H13C H -0.244062 0.242109 0.624182 0.062 Uiso 1 1 calc R U . . .
C14 C -0.0772(4) 0.4324(3) 0.7423(2) 0.0393(7) Uani 1 1 d . . . . .
H14A H 0.015822 0.403314 0.781334 0.059 Uiso 1 1 calc R U . . .
H14B H -0.161282 0.423587 0.775219 0.059 Uiso 1 1 calc R U . . .
H14C H -0.063358 0.509645 0.730198 0.059 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 N2 2.228(2) . ?
I1 N1 2.271(2) . ?
S1 O2 1.435(2) . ?
S1 O1 1.435(2) . ?
S1 N1 1.639(2) . ?
S1 C1 1.755(3) . ?
O3 C7 1.218(3) . ?
N1 C7 1.378(4) . ?
N2 C12 1.344(4) . ?
N2 C8 1.355(4) . ?
N3 C10 1.344(4) . ?
N3 C13 1.457(4) . ?
N3 C14 1.460(4) . ?
C1 C2 1.383(4) . ?
C1 C6 1.388(4) . ?
C2 C3 1.384(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.491(4) . ?
C8 C9 1.362(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.416(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.419(4) . ?
C11 C12 1.356(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
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
N2 I1 N1 175.59(8) . . ?
O2 S1 O1 115.63(13) . . ?
O2 S1 N1 111.03(12) . . ?
O1 S1 N1 110.56(13) . . ?
O2 S1 C1 111.25(13) . . ?
O1 S1 C1 111.75(12) . . ?
N1 S1 C1 94.72(13) . . ?
C7 N1 S1 113.9(2) . . ?
C7 N1 I1 128.40(19) . . ?
S1 N1 I1 117.61(13) . . ?
C12 N2 C8 117.7(3) . . ?
C12 N2 I1 120.51(19) . . ?
C8 N2 I1 121.70(19) . . ?
C10 N3 C13 120.9(3) . . ?
C10 N3 C14 120.9(3) . . ?
C13 N3 C14 118.2(3) . . ?
C2 C1 C6 122.8(3) . . ?
C2 C1 S1 128.6(2) . . ?
C6 C1 S1 108.6(2) . . ?
C1 C2 C3 117.1(3) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 H2 121.4 . . ?
C2 C3 C4 120.9(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 121.6(3) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 117.9(3) . . ?
C6 C5 H5 121.1 . . ?
C4 C5 H5 121.1 . . ?
C5 C6 C1 119.7(3) . . ?
C5 C6 C7 127.8(3) . . ?
C1 C6 C7 112.4(2) . . ?
O3 C7 N1 124.6(3) . . ?
O3 C7 C6 125.2(3) . . ?
N1 C7 C6 110.2(2) . . ?
N2 C8 C9 122.6(3) . . ?
N2 C8 H8 118.7 . . ?
C9 C8 H8 118.7 . . ?
C8 C9 C10 120.6(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
N3 C10 C9 122.6(3) . . ?
N3 C10 C11 122.1(3) . . ?
C9 C10 C11 115.3(3) . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
N2 C12 C11 123.3(3) . . ?
N2 C12 H12 118.4 . . ?
C11 C12 H12 118.4 . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_refine_diff_density_max         0.452
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.100



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

data_3c
_database_code_depnum_ccdc_archive 'CCDC 2255943'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        OID-004-3
_chemical_name_common            NISac+4-Morpholinopyridine
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 I N3 O4 S'
_chemical_formula_sum            'C16 H16 I N3 O4 S'
_chemical_formula_weight         473.28

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.1810(3)
_cell_length_b                   8.3001(4)
_cell_length_c                   15.0946(9)
_cell_angle_alpha                94.226(2)
_cell_angle_beta                 101.222(2)
_cell_angle_gamma                118.108(3)
_cell_volume                     870.45(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    1756
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      28.700

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.806
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    1.986
_shelx_estimated_absorpt_T_min   0.597
_shelx_estimated_absorpt_T_max   0.692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6210
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5984
_diffrn_reflns_av_unetI/netI     0.1105
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.803
_diffrn_reflns_theta_max         26.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3476
_reflns_number_gt                2633
_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0013P)²+4.0056P] 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         3476
_refine_ls_number_parameters     226
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0593
_refine_ls_wR_factor_ref         0.1343
_refine_ls_wR_factor_gt          0.1162
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.098
_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 0.30501(7) 0.55135(7) 0.37756(4) 0.02091(17) Uani 1 1 d . . . . .
S1 S 0.0980(3) 0.2794(2) 0.16106(14) 0.0200(4) Uani 1 1 d . . . . .
O1 O 0.2310(7) 0.2114(7) 0.1622(4) 0.0251(13) Uani 1 1 d . . . . .
O2 O 0.1349(8) 0.4359(7) 0.1174(4) 0.0307(14) Uani 1 1 d . . . . .
O3 O -0.1581(8) 0.2086(8) 0.3442(4) 0.0332(15) Uani 1 1 d . . . . .
O4 O 1.2506(8) 1.5324(7) 0.8332(4) 0.0332(14) Uani 1 1 d . . . . .
N1 N 0.0726(8) 0.3162(8) 0.2638(5) 0.0228(15) Uani 1 1 d . . . . .
N2 N 0.5338(9) 0.7899(8) 0.4899(5) 0.0226(15) Uani 1 1 d . . . . .
N3 N 0.9858(9) 1.2055(8) 0.7013(5) 0.0222(15) Uani 1 1 d . . . . .
C1 C -0.1396(10) 0.0952(9) 0.1156(6) 0.0198(17) Uani 1 1 d . . . . .
C2 C -0.2252(11) -0.0101(10) 0.0278(6) 0.0233(18) Uani 1 1 d . . . . .
H2 H -0.158887 0.014237 -0.019049 0.028 Uiso 1 1 calc R U . . .
C3 C -0.4150(11) -0.1548(11) 0.0113(6) 0.029(2) Uani 1 1 d . . . . .
H3 H -0.479449 -0.232879 -0.047705 0.035 Uiso 1 1 calc R U . . .
C4 C -0.5107(11) -0.1853(11) 0.0816(7) 0.030(2) Uani 1 1 d . . . . .
H4 H -0.640363 -0.282042 0.068786 0.036 Uiso 1 1 calc R U . . .
C5 C -0.4199(10) -0.0774(10) 0.1687(6) 0.0237(18) Uani 1 1 d . . . . .
H5 H -0.484678 -0.100915 0.216167 0.028 Uiso 1 1 calc R U . . .
C6 C -0.2331(10) 0.0655(9) 0.1855(5) 0.0194(17) Uani 1 1 d . . . . .
C7 C -0.1090(11) 0.2012(10) 0.2741(6) 0.0206(17) Uani 1 1 d . . . . .
C8 C 0.8418(11) 1.0656(10) 0.5389(6) 0.0259(19) Uani 1 1 d . . . . .
H8 H 0.947842 1.160246 0.522363 0.031 Uiso 1 1 calc R U . . .
C9 C 0.6934(11) 0.9234(10) 0.4722(6) 0.0240(18) Uani 1 1 d . . . . .
H9 H 0.703399 0.918609 0.410488 0.029 Uiso 1 1 calc R U . . .
C10 C 0.5254(11) 0.7986(10) 0.5773(6) 0.026(2) Uani 1 1 d . . . . .
H10 H 0.413968 0.705154 0.590719 0.031 Uiso 1 1 calc R U . . .
C11 C 0.6654(11) 0.9320(10) 0.6486(6) 0.0257(19) Uani 1 1 d . . . . .
H11 H 0.648940 0.932569 0.709177 0.031 Uiso 1 1 calc R U . . .
C12 C 0.8373(11) 1.0714(10) 0.6315(6) 0.0224(18) Uani 1 1 d . . . . .
C13 C 1.1401(10) 1.3629(10) 0.6748(6) 0.0229(18) Uani 1 1 d . . . . .
H13A H 1.090434 1.441270 0.647628 0.027 Uiso 1 1 calc R U . . .
H13B H 1.184039 1.315076 0.627876 0.027 Uiso 1 1 calc R U . . .
C14 C 1.3084(12) 1.4796(11) 0.7590(6) 0.035(2) Uani 1 1 d . . . . .
H14A H 1.371980 1.407411 0.778944 0.042 Uiso 1 1 calc R U . . .
H14B H 1.403330 1.592921 0.741854 0.042 Uiso 1 1 calc R U . . .
C15 C 1.1302(12) 1.3667(10) 0.8634(6) 0.0293(19) Uani 1 1 d . . . . .
H15A H 1.099128 1.401341 0.919492 0.035 Uiso 1 1 calc R U . . .
H15B H 1.200352 1.298532 0.879380 0.035 Uiso 1 1 calc R U . . .
C16 C 0.9473(11) 1.2421(10) 0.7903(6) 0.0244(18) Uani 1 1 d . . . . .
H16A H 0.875530 1.122690 0.810046 0.029 Uiso 1 1 calc R U . . .
H16B H 0.866347 1.301409 0.782354 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 N2 2.253(6) . ?
I1 N1 2.261(6) . ?
S1 O2 1.430(5) . ?
S1 O1 1.441(5) . ?
S1 N1 1.630(7) . ?
S1 C1 1.765(7) . ?
O3 C7 1.209(9) . ?
O4 C14 1.414(11) . ?
O4 C15 1.436(9) . ?
N1 C7 1.386(9) . ?
N2 C10 1.334(10) . ?
N2 C9 1.349(10) . ?
N3 C12 1.371(10) . ?
N3 C13 1.476(9) . ?
N3 C16 1.481(10) . ?
C1 C2 1.379(11) . ?
C1 C6 1.391(11) . ?
C2 C3 1.401(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.406(12) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(12) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(10) . ?
C5 H5 0.9500 . ?
C6 C7 1.504(11) . ?
C8 C9 1.371(11) . ?
C8 C12 1.403(12) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.358(11) . ?
C10 H10 0.9500 . ?
C11 C12 1.427(11) . ?
C11 H11 0.9500 . ?
C13 C14 1.526(11) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.503(11) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 I1 N1 178.7(2) . . ?
O2 S1 O1 115.7(3) . . ?
O2 S1 N1 111.5(3) . . ?
O1 S1 N1 111.2(4) . . ?
O2 S1 C1 111.6(3) . . ?
O1 S1 C1 110.1(3) . . ?
N1 S1 C1 94.9(4) . . ?
C14 O4 C15 108.0(6) . . ?
C7 N1 S1 114.6(5) . . ?
C7 N1 I1 122.0(5) . . ?
S1 N1 I1 123.2(3) . . ?
C10 N2 C9 117.0(7) . . ?
C10 N2 I1 122.0(5) . . ?
C9 N2 I1 120.8(6) . . ?
C12 N3 C13 117.2(7) . . ?
C12 N3 C16 118.7(6) . . ?
C13 N3 C16 117.2(6) . . ?
C2 C1 C6 123.3(7) . . ?
C2 C1 S1 128.4(6) . . ?
C6 C1 S1 108.2(6) . . ?
C1 C2 C3 116.5(8) . . ?
C1 C2 H2 121.7 . . ?
C3 C2 H2 121.7 . . ?
C2 C3 C4 120.5(8) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 121.3(7) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C6 C5 C4 118.6(8) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C1 119.8(7) . . ?
C5 C6 C7 127.5(7) . . ?
C1 C6 C7 112.8(6) . . ?
O3 C7 N1 124.9(8) . . ?
O3 C7 C6 125.7(7) . . ?
N1 C7 C6 109.4(7) . . ?
C9 C8 C12 120.1(7) . . ?
C9 C8 H8 120.0 . . ?
C12 C8 H8 120.0 . . ?
N2 C9 C8 123.2(8) . . ?
N2 C9 H9 118.4 . . ?
C8 C9 H9 118.4 . . ?
N2 C10 C11 124.5(7) . . ?
N2 C10 H10 117.8 . . ?
C11 C10 H10 117.8 . . ?
C10 C11 C12 119.3(8) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
N3 C12 C8 122.4(7) . . ?
N3 C12 C11 121.7(8) . . ?
C8 C12 C11 115.8(7) . . ?
N3 C13 C14 110.1(7) . . ?
N3 C13 H13A 109.6 . . ?
C14 C13 H13A 109.6 . . ?
N3 C13 H13B 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.2 . . ?
O4 C14 C13 112.5(7) . . ?
O4 C14 H14A 109.1 . . ?
C13 C14 H14A 109.1 . . ?
O4 C14 H14B 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
O4 C15 C16 111.4(7) . . ?
O4 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
O4 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
N3 C16 C15 111.5(7) . . ?
N3 C16 H16A 109.3 . . ?
C15 C16 H16A 109.3 . . ?
N3 C16 H16B 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?

_refine_diff_density_max         1.137
_refine_diff_density_min         -1.129
_refine_diff_density_rms         0.222



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

data_3b
_database_code_depnum_ccdc_archive 'CCDC 2255942'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        TIG-191
_chemical_name_common            NISac+4-Pyrrolidinopyridine
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 I N3 O3 S'
_chemical_formula_sum            'C16 H16 I N3 O3 S'
_chemical_formula_weight         457.28

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.9856(2)
_cell_length_b                   8.3116(4)
_cell_length_c                   13.2390(6)
_cell_angle_alpha                78.2750(10)
_cell_angle_beta                 89.168(2)
_cell_angle_gamma                75.7100(10)
_cell_volume                     833.17(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    2003
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      28.700

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_F_000             452
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    2.067
_shelx_estimated_absorpt_T_min   0.523
_shelx_estimated_absorpt_T_max   0.869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5998
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6421
_diffrn_reflns_av_unetI/netI     0.0780
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.584
_diffrn_reflns_theta_max         26.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3353
_reflns_number_gt                2766
_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0189P)²+3.8591P] 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         3353
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1088
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.72147(5) 0.57265(5) 0.63335(3) 0.02396(14) Uani 1 1 d . . . . .
S1 S 0.76296(19) 0.2769(2) 0.86244(12) 0.0247(3) Uani 1 1 d . . . . .
O1 O 0.6890(6) 0.3833(6) 0.9325(4) 0.0373(11) Uani 1 1 d . . . . .
O2 O 0.9487(5) 0.2424(6) 0.8538(4) 0.0346(11) Uani 1 1 d . . . . .
O3 O 0.4980(5) 0.2695(6) 0.6370(3) 0.0294(10) Uani 1 1 d . . . . .
N1 N 0.6672(6) 0.3476(6) 0.7481(4) 0.0237(11) Uani 1 1 d . . . . .
N2 N 0.7779(6) 0.7926(7) 0.5213(4) 0.0266(12) Uani 1 1 d . . . . .
N3 N 0.8460(6) 1.2055(7) 0.3052(4) 0.0249(11) Uani 1 1 d . . . . .
C1 C 0.6953(7) 0.0870(8) 0.8865(5) 0.0234(13) Uani 1 1 d . . . . .
C2 C 0.7384(8) -0.0496(8) 0.9692(5) 0.0300(15) Uani 1 1 d . . . . .
H2 H 0.810292 -0.048599 1.025559 0.036 Uiso 1 1 calc R U . . .
C3 C 0.6722(8) -0.1872(8) 0.9661(5) 0.0320(15) Uani 1 1 d . . . . .
H3 H 0.700714 -0.283818 1.021009 0.038 Uiso 1 1 calc R U . . .
C4 C 0.5649(8) -0.1873(9) 0.8845(6) 0.0360(16) Uani 1 1 d . . . . .
H4 H 0.517806 -0.281999 0.885663 0.043 Uiso 1 1 calc R U . . .
C5 C 0.5258(8) -0.0506(8) 0.8014(5) 0.0269(14) Uani 1 1 d . . . . .
H5 H 0.454735 -0.051772 0.744766 0.032 Uiso 1 1 calc R U . . .
C6 C 0.5927(7) 0.0871(7) 0.8029(5) 0.0210(13) Uani 1 1 d . . . . .
C7 C 0.5768(7) 0.2432(8) 0.7187(5) 0.0232(13) Uani 1 1 d . . . . .
C8 C 0.8556(8) 0.7715(8) 0.4322(5) 0.0278(14) Uani 1 1 d . . . . .
H8 H 0.892077 0.660241 0.418865 0.033 Uiso 1 1 calc R U . . .
C9 C 0.8832(8) 0.9034(8) 0.3611(5) 0.0291(15) Uani 1 1 d . . . . .
H9 H 0.941356 0.882672 0.300167 0.035 Uiso 1 1 calc R U . . .
C10 C 0.8270(7) 1.0710(7) 0.3762(5) 0.0205(12) Uani 1 1 d . . . . .
C11 C 0.7481(8) 1.0897(8) 0.4715(5) 0.0268(14) Uani 1 1 d . . . . .
H11 H 0.711276 1.198912 0.487713 0.032 Uiso 1 1 calc R U . . .
C12 C 0.7257(8) 0.9526(9) 0.5386(5) 0.0303(15) Uani 1 1 d . . . . .
H12 H 0.670601 0.968407 0.601146 0.036 Uiso 1 1 calc R U . . .
C13 C 0.7905(8) 1.3821(8) 0.3177(5) 0.0296(15) Uani 1 1 d . . . . .
H13A H 0.873755 1.408201 0.362729 0.036 Uiso 1 1 calc R U . . .
H13B H 0.674599 1.405505 0.347327 0.036 Uiso 1 1 calc R U . . .
C14 C 0.7867(8) 1.4833(8) 0.2085(5) 0.0327(15) Uani 1 1 d . . . . .
H14A H 0.809836 1.595082 0.207974 0.039 Uiso 1 1 calc R U . . .
H14B H 0.673431 1.500855 0.172878 0.039 Uiso 1 1 calc R U . . .
C15 C 0.9319(8) 1.3718(9) 0.1574(5) 0.0341(16) Uani 1 1 d . . . . .
H15A H 0.910948 1.395669 0.081652 0.041 Uiso 1 1 calc R U . . .
H15B H 1.045485 1.391440 0.172239 0.041 Uiso 1 1 calc R U . . .
C16 C 0.9254(9) 1.1914(9) 0.2053(5) 0.0346(16) Uani 1 1 d . . . . .
H16A H 0.854174 1.148431 0.161570 0.042 Uiso 1 1 calc R U . . .
H16B H 1.043041 1.114642 0.215163 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 N2 2.243(5) . ?
I1 N1 2.285(5) . ?
S1 O1 1.432(5) . ?
S1 O2 1.447(4) . ?
S1 N1 1.635(5) . ?
S1 C1 1.760(7) . ?
O3 C7 1.212(7) . ?
N1 C7 1.371(8) . ?
N2 C8 1.348(8) . ?
N2 C12 1.356(8) . ?
N3 C10 1.344(8) . ?
N3 C13 1.468(8) . ?
N3 C16 1.472(8) . ?
C1 C2 1.385(9) . ?
C1 C6 1.386(8) . ?
C2 C3 1.381(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(10) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.509(8) . ?
C8 C9 1.353(9) . ?
C8 H8 0.9500 . ?
C9 C10 1.409(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.422(8) . ?
C11 C12 1.343(9) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.514(9) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.537(9) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.518(10) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 I1 N1 179.35(18) . . ?
O1 S1 O2 116.5(3) . . ?
O1 S1 N1 111.1(3) . . ?
O2 S1 N1 110.2(3) . . ?
O1 S1 C1 111.4(3) . . ?
O2 S1 C1 110.7(3) . . ?
N1 S1 C1 94.9(3) . . ?
C7 N1 S1 114.5(4) . . ?
C7 N1 I1 121.5(4) . . ?
S1 N1 I1 122.9(3) . . ?
C8 N2 C12 118.0(6) . . ?
C8 N2 I1 121.1(4) . . ?
C12 N2 I1 120.8(4) . . ?
C10 N3 C13 124.4(5) . . ?
C10 N3 C16 123.4(5) . . ?
C13 N3 C16 112.2(5) . . ?
C2 C1 C6 122.4(6) . . ?
C2 C1 S1 129.2(5) . . ?
C6 C1 S1 108.3(5) . . ?
C3 C2 C1 117.0(6) . . ?
C3 C2 H2 121.5 . . ?
C1 C2 H2 121.5 . . ?
C2 C3 C4 121.5(6) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 120.7(6) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C6 C5 C4 118.4(6) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C5 C6 C1 120.0(6) . . ?
C5 C6 C7 127.4(6) . . ?
C1 C6 C7 112.5(5) . . ?
O3 C7 N1 125.7(6) . . ?
O3 C7 C6 124.6(6) . . ?
N1 C7 C6 109.7(5) . . ?
N2 C8 C9 122.2(6) . . ?
N2 C8 H8 118.9 . . ?
C9 C8 H8 118.9 . . ?
C8 C9 C10 120.9(6) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
N3 C10 C9 122.4(5) . . ?
N3 C10 C11 121.8(5) . . ?
C9 C10 C11 115.7(6) . . ?
C12 C11 C10 119.9(6) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 N2 123.2(6) . . ?
C11 C12 H12 118.4 . . ?
N2 C12 H12 118.4 . . ?
N3 C13 C14 103.3(5) . . ?
N3 C13 H13A 111.1 . . ?
C14 C13 H13A 111.1 . . ?
N3 C13 H13B 111.1 . . ?
C14 C13 H13B 111.1 . . ?
H13A C13 H13B 109.1 . . ?
C13 C14 C15 103.5(5) . . ?
C13 C14 H14A 111.1 . . ?
C15 C14 H14A 111.1 . . ?
C13 C14 H14B 111.1 . . ?
C15 C14 H14B 111.1 . . ?
H14A C14 H14B 109.0 . . ?
C16 C15 C14 104.4(5) . . ?
C16 C15 H15A 110.9 . . ?
C14 C15 H15A 110.9 . . ?
C16 C15 H15B 110.9 . . ?
C14 C15 H15B 110.9 . . ?
H15A C15 H15B 108.9 . . ?
N3 C16 C15 103.8(5) . . ?
N3 C16 H16A 111.0 . . ?
C15 C16 H16A 111.0 . . ?
N3 C16 H16B 111.0 . . ?
C15 C16 H16B 111.0 . . ?
H16A C16 H16B 109.0 . . ?

_refine_diff_density_max         0.744
_refine_diff_density_min         -0.734
_refine_diff_density_rms         0.167



####################################################################### 
# 
# 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_3d
_database_code_depnum_ccdc_archive 'CCDC 2255944'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        OID-003-4
_chemical_name_common            NISac+4-Piperidinopyridine
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H18 I N3 O3 S'
_chemical_formula_sum            'C17 H18 I N3 O3 S'
_chemical_formula_weight         471.30

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.2544(4)
_cell_length_b                   8.3834(5)
_cell_length_c                   13.5305(9)
_cell_angle_alpha                78.889(2)
_cell_angle_beta                 91.709(3)
_cell_angle_gamma                77.131(2)
_cell_volume                     893.09(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    2505
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      28.700

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.932
_shelx_estimated_absorpt_T_min   0.735
_shelx_estimated_absorpt_T_max   0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6489
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6963
_diffrn_reflns_av_unetI/netI     0.1148
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.538
_diffrn_reflns_theta_max         26.247
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3581
_reflns_number_gt                2558
_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0543P)²+3.7925P] 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         3581
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1066
_refine_ls_R_factor_gt           0.0673
_refine_ls_wR_factor_ref         0.1409
_refine_ls_wR_factor_gt          0.1233
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 0.79019(7) 0.45276(7) 0.37260(4) 0.02708(19) Uani 1 1 d . . . . .
S1 S 0.7349(3) 0.7282(3) 0.14682(15) 0.0293(5) Uani 1 1 d . . . . .
O1 O 0.5571(8) 0.7624(8) 0.1491(5) 0.0431(16) Uani 1 1 d . . . . .
O2 O 0.8086(8) 0.6093(7) 0.0889(4) 0.0417(16) Uani 1 1 d . . . . .
O3 O 0.9888(7) 0.7781(7) 0.3641(4) 0.0343(14) Uani 1 1 d . . . . .
N1 N 0.8252(8) 0.6792(8) 0.2614(5) 0.0246(15) Uani 1 1 d . . . . .
N2 N 0.7369(8) 0.2336(8) 0.4786(5) 0.0260(15) Uani 1 1 d . . . . .
N3 N 0.6098(10) -0.1687(9) 0.6676(6) 0.045(2) Uani 1 1 d . . . . .
C1 C 0.8020(10) 0.9154(9) 0.1132(6) 0.0243(18) Uani 1 1 d . . . . .
C2 C 0.7670(11) 1.0336(10) 0.0255(7) 0.035(2) Uani 1 1 d . . . . .
H2 H 0.700008 1.020927 -0.029464 0.042 Uiso 1 1 calc R U . . .
C3 C 0.8333(13) 1.1723(11) 0.0202(8) 0.044(2) Uani 1 1 d . . . . .
H3 H 0.810760 1.257026 -0.039518 0.053 Uiso 1 1 calc R U . . .
C4 C 0.9307(13) 1.1900(11) 0.0989(8) 0.045(3) Uani 1 1 d . . . . .
H4 H 0.974768 1.286678 0.092554 0.054 Uiso 1 1 calc R U . . .
C5 C 0.9669(11) 1.0703(11) 0.1882(7) 0.037(2) Uani 1 1 d . . . . .
H5 H 1.035358 1.082316 0.242689 0.045 Uiso 1 1 calc R U . . .
C6 C 0.8982(10) 0.9329(10) 0.1937(6) 0.0262(18) Uani 1 1 d . . . . .
C7 C 0.9122(10) 0.7917(10) 0.2825(6) 0.0260(18) Uani 1 1 d . . . . .
C8 C 0.7578(10) -0.0602(10) 0.5269(6) 0.0247(18) Uani 1 1 d . . . . .
H8 H 0.802452 -0.169010 0.515212 0.030 Uiso 1 1 calc R U . . .
C9 C 0.7925(10) 0.0754(10) 0.4657(6) 0.0273(19) Uani 1 1 d . . . . .
H9 H 0.859191 0.057669 0.411023 0.033 Uiso 1 1 calc R U . . .
C10 C 0.6451(10) 0.2548(10) 0.5570(6) 0.0277(19) Uani 1 1 d . . . . .
H10 H 0.607622 0.364714 0.568738 0.033 Uiso 1 1 calc R U . . .
C11 C 0.6031(10) 0.1271(10) 0.6204(6) 0.0291(19) Uani 1 1 d . . . . .
H11 H 0.536852 0.150132 0.674459 0.035 Uiso 1 1 calc R U . . .
C12 C 0.6556(10) -0.0399(10) 0.6081(6) 0.0303(19) Uani 1 1 d . . . . .
C13 C 0.6724(11) -0.3433(10) 0.6637(7) 0.035(2) Uani 1 1 d . . . . .
H13A H 0.746627 -0.351736 0.607857 0.042 Uiso 1 1 calc R U . . .
H13B H 0.577898 -0.392747 0.649948 0.042 Uiso 1 1 calc R U . . .
C14 C 0.7664(13) -0.4388(11) 0.7611(7) 0.050(3) Uani 1 1 d . . . . .
H14A H 0.870937 -0.401553 0.768922 0.060 Uiso 1 1 calc R U . . .
H14B H 0.796693 -0.559155 0.759113 0.060 Uiso 1 1 calc R U . . .
C15 C 0.6663(16) -0.4149(12) 0.8510(7) 0.064(3) Uani 1 1 d . . . . .
H15A H 0.573423 -0.471787 0.850295 0.076 Uiso 1 1 calc R U . . .
H15B H 0.738324 -0.466965 0.913976 0.076 Uiso 1 1 calc R U . . .
C16 C 0.5974(12) -0.2334(11) 0.8501(7) 0.043(2) Uani 1 1 d . . . . .
H16A H 0.689584 -0.179432 0.861368 0.051 Uiso 1 1 calc R U . . .
H16B H 0.522402 -0.221845 0.905403 0.051 Uiso 1 1 calc R U . . .
C17 C 0.5028(12) -0.1490(12) 0.7508(7) 0.042(2) Uani 1 1 d . . . . .
H17A H 0.406123 -0.197969 0.741850 0.050 Uiso 1 1 calc R U . . .
H17B H 0.460274 -0.028564 0.749939 0.050 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 N2 2.238(6) . ?
I1 N1 2.263(6) . ?
S1 O2 1.427(6) . ?
S1 O1 1.433(6) . ?
S1 N1 1.636(6) . ?
S1 C1 1.762(7) . ?
O3 C7 1.228(9) . ?
N1 C7 1.371(9) . ?
N2 C10 1.339(10) . ?
N2 C9 1.351(10) . ?
N3 C12 1.350(11) . ?
N3 C13 1.451(10) . ?
N3 C17 1.462(11) . ?
C1 C2 1.368(11) . ?
C1 C6 1.379(11) . ?
C2 C3 1.382(12) . ?
C2 H2 0.9500 . ?
C3 C4 1.367(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(13) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(11) . ?
C5 H5 0.9500 . ?
C6 C7 1.497(11) . ?
C8 C9 1.363(11) . ?
C8 C12 1.418(11) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.353(11) . ?
C10 H10 0.9500 . ?
C11 C12 1.414(11) . ?
C11 H11 0.9500 . ?
C13 C14 1.495(12) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.511(14) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.499(13) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.497(13) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 I1 N1 176.0(2) . . ?
O2 S1 O1 116.8(4) . . ?
O2 S1 N1 110.5(4) . . ?
O1 S1 N1 110.8(4) . . ?
O2 S1 C1 111.2(4) . . ?
O1 S1 C1 110.6(4) . . ?
N1 S1 C1 94.7(3) . . ?
C7 N1 S1 113.7(5) . . ?
C7 N1 I1 125.3(5) . . ?
S1 N1 I1 120.9(3) . . ?
C10 N2 C9 117.0(7) . . ?
C10 N2 I1 121.0(5) . . ?
C9 N2 I1 122.0(5) . . ?
C12 N3 C13 124.6(7) . . ?
C12 N3 C17 123.3(7) . . ?
C13 N3 C17 111.8(7) . . ?
C2 C1 C6 121.9(7) . . ?
C2 C1 S1 129.3(6) . . ?
C6 C1 S1 108.7(6) . . ?
C1 C2 C3 117.2(9) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 H2 121.4 . . ?
C4 C3 C2 121.4(9) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 121.7(8) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 116.7(9) . . ?
C6 C5 H5 121.7 . . ?
C4 C5 H5 121.7 . . ?
C1 C6 C5 121.0(8) . . ?
C1 C6 C7 112.1(6) . . ?
C5 C6 C7 126.9(8) . . ?
O3 C7 N1 124.0(7) . . ?
O3 C7 C6 125.2(7) . . ?
N1 C7 C6 110.7(7) . . ?
C9 C8 C12 120.4(7) . . ?
C9 C8 H8 119.8 . . ?
C12 C8 H8 119.8 . . ?
N2 C9 C8 123.4(7) . . ?
N2 C9 H9 118.3 . . ?
C8 C9 H9 118.3 . . ?
N2 C10 C11 123.2(7) . . ?
N2 C10 H10 118.4 . . ?
C11 C10 H10 118.4 . . ?
C10 C11 C12 121.5(8) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
N3 C12 C11 122.8(8) . . ?
N3 C12 C8 122.8(7) . . ?
C11 C12 C8 114.4(7) . . ?
N3 C13 C14 110.9(7) . . ?
N3 C13 H13A 109.5 . . ?
C14 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 112.1(8) . . ?
C13 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C14 111.5(8) . . ?
C16 C15 H15A 109.3 . . ?
C14 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C15 C16 C17 109.9(8) . . ?
C15 C16 H16A 109.7 . . ?
C17 C16 H16A 109.7 . . ?
C15 C16 H16B 109.7 . . ?
C17 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
N3 C17 C16 110.7(8) . . ?
N3 C17 H17A 109.5 . . ?
C16 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?

_refine_diff_density_max         0.910
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.176



####################################################################### 
# 
# 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_4a_2
_database_code_depnum_ccdc_archive 'CCDC 2255946'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        THY-510
_chemical_name_common            (NISac+DMAP)+DMAP
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 I N4, C7 H4 N O3 S'
_chemical_formula_sum            'C21 H24 I N5 O3 S'
_chemical_formula_weight         553.41

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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                   9.1690(3)
_cell_length_b                   15.4714(4)
_cell_length_c                   31.9040(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4525.8(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    6111
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      28.283

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_F_000             2224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    1.540
_shelx_estimated_absorpt_T_min   0.791
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6507
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35212
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.554
_diffrn_reflns_theta_max         26.246
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4565
_reflns_number_gt                3063
_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0171P)²+4.4594P] 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         4565
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.0733
_refine_ls_wR_factor_gt          0.0656
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.004
_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 -0.00967(3) 0.60310(2) 0.73934(2) 0.03369(9) Uani 1 1 d . . . . .
N1 N 0.0212(3) 0.6304(2) 0.80796(9) 0.0326(8) Uani 1 1 d . . . . .
N2 N 0.0493(3) 0.6909(2) 0.93475(9) 0.0307(8) Uani 1 1 d . . . . .
N3 N -0.0501(3) 0.5774(2) 0.67090(10) 0.0315(8) Uani 1 1 d . . . . .
N4 N -0.1557(3) 0.5509(2) 0.54513(9) 0.0323(8) Uani 1 1 d . . . . .
C1 C 0.1324(4) 0.7094(2) 0.86338(11) 0.0297(9) Uani 1 1 d . . . . .
H1 H 0.203994 0.750137 0.871972 0.036 Uiso 1 1 calc R U . . .
C2 C 0.1210(4) 0.6877(2) 0.82216(12) 0.0310(9) Uani 1 1 d . . . . .
H2 H 0.185593 0.713740 0.802623 0.037 Uiso 1 1 calc R U . . .
C3 C -0.0701(4) 0.5947(3) 0.83609(13) 0.0370(10) Uani 1 1 d . . . . .
H3 H -0.141029 0.554674 0.826379 0.044 Uiso 1 1 calc R U . . .
C4 C -0.0657(4) 0.6133(2) 0.87798(12) 0.0337(9) Uani 1 1 d . . . . .
H4 H -0.133097 0.586788 0.896578 0.040 Uiso 1 1 calc R U . . .
C5 C 0.0386(4) 0.6719(2) 0.89352(12) 0.0281(9) Uani 1 1 d . . . . .
C6 C 0.1452(4) 0.7601(3) 0.94896(12) 0.0389(10) Uani 1 1 d . . . . .
H6A H 0.242538 0.752025 0.936903 0.058 Uiso 1 1 calc R U . . .
H6B H 0.151735 0.758915 0.979611 0.058 Uiso 1 1 calc R U . . .
H6C H 0.105719 0.815950 0.939909 0.058 Uiso 1 1 calc R U . . .
C7 C -0.0584(4) 0.6590(3) 0.96451(12) 0.0363(10) Uani 1 1 d . . . . .
H7A H -0.150660 0.689815 0.960408 0.054 Uiso 1 1 calc R U . . .
H7B H -0.023324 0.668686 0.993148 0.054 Uiso 1 1 calc R U . . .
H7C H -0.073667 0.596989 0.960013 0.054 Uiso 1 1 calc R U . . .
C8 C -0.1870(4) 0.5078(2) 0.61734(11) 0.0266(9) Uani 1 1 d . . . . .
H8 H -0.257795 0.465678 0.609914 0.032 Uiso 1 1 calc R U . . .
C9 C -0.1513(4) 0.5204(2) 0.65834(11) 0.0302(9) Uani 1 1 d . . . . .
H9 H -0.200494 0.487277 0.679029 0.036 Uiso 1 1 calc R U . . .
C10 C 0.0209(4) 0.6229(2) 0.64102(12) 0.0341(9) Uani 1 1 d . . . . .
H10 H 0.094263 0.662572 0.649553 0.041 Uiso 1 1 calc R U . . .
C11 C -0.0073(4) 0.6148(2) 0.59948(12) 0.0349(9) Uani 1 1 d . . . . .
H11 H 0.047145 0.647203 0.579617 0.042 Uiso 1 1 calc R U . . .
C12 C -0.1181(4) 0.5577(2) 0.58588(11) 0.0268(8) Uani 1 1 d . . . . .
C13 C -0.2770(4) 0.4961(2) 0.53230(12) 0.0342(10) Uani 1 1 d . . . . .
H13A H -0.249698 0.435285 0.535672 0.051 Uiso 1 1 calc R U . . .
H13B H -0.300529 0.507475 0.502852 0.051 Uiso 1 1 calc R U . . .
H13C H -0.362273 0.508796 0.549765 0.051 Uiso 1 1 calc R U . . .
C14 C -0.0840(4) 0.6030(3) 0.51294(12) 0.0416(10) Uani 1 1 d . . . . .
H14A H -0.096012 0.664413 0.519531 0.062 Uiso 1 1 calc R U . . .
H14B H -0.128091 0.590649 0.485596 0.062 Uiso 1 1 calc R U . . .
H14C H 0.020071 0.588707 0.512093 0.062 Uiso 1 1 calc R U . . .
S1 S 0.61639(11) 0.86192(6) 0.91187(3) 0.0276(2) Uani 1 1 d . . . . .
O1 O 0.6546(3) 0.78643(16) 0.93638(8) 0.0344(6) Uani 1 1 d . . . . .
O2 O 0.6393(3) 0.94253(17) 0.93378(8) 0.0376(7) Uani 1 1 d . . . . .
O3 O 0.3487(3) 0.84986(17) 0.82739(8) 0.0335(7) Uani 1 1 d . . . . .
N5 N 0.4545(3) 0.8546(2) 0.89262(9) 0.0297(7) Uani 1 1 d . . . . .
C15 C 0.7135(4) 0.8620(2) 0.86364(10) 0.0245(8) Uani 1 1 d . . . . .
C16 C 0.8600(4) 0.8680(2) 0.85517(12) 0.0333(9) Uani 1 1 d . . . . .
H16 H 0.929824 0.873338 0.877004 0.040 Uiso 1 1 calc R U . . .
C17 C 0.9016(4) 0.8661(3) 0.81347(12) 0.0383(10) Uani 1 1 d . . . . .
H17 H 1.002124 0.869375 0.806491 0.046 Uiso 1 1 calc R U . . .
C18 C 0.7993(4) 0.8593(3) 0.78186(13) 0.0391(10) Uani 1 1 d . . . . .
H18 H 0.830678 0.858301 0.753482 0.047 Uiso 1 1 calc R U . . .
C19 C 0.6520(4) 0.8541(2) 0.79084(11) 0.0313(9) Uani 1 1 d . . . . .
H19 H 0.581903 0.849144 0.769037 0.038 Uiso 1 1 calc R U . . .
C20 C 0.6094(4) 0.8562(2) 0.83247(11) 0.0237(8) Uani 1 1 d . . . . .
C21 C 0.4576(4) 0.8529(2) 0.84983(11) 0.0262(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 N1 2.248(3) . ?
I1 N3 2.250(3) . ?
N1 C3 1.346(5) . ?
N1 C2 1.351(5) . ?
N2 C5 1.352(4) . ?
N2 C7 1.456(5) . ?
N2 C6 1.457(5) . ?
N3 C9 1.342(4) . ?
N3 C10 1.352(5) . ?
N4 C12 1.349(4) . ?
N4 C13 1.457(4) . ?
N4 C14 1.461(5) . ?
C1 C2 1.361(5) . ?
C1 C5 1.415(5) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C4 1.368(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.407(5) . ?
C4 H4 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.362(5) . ?
C8 C12 1.414(5) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.356(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.415(5) . ?
C11 H11 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
S1 O2 1.445(3) . ?
S1 O1 1.448(3) . ?
S1 N5 1.610(3) . ?
S1 C15 1.778(3) . ?
O3 C21 1.230(4) . ?
N5 C21 1.366(4) . ?
C15 C16 1.373(5) . ?
C15 C20 1.381(5) . ?
C16 C17 1.384(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.381(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.383(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.385(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.498(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 I1 N3 177.67(11) . . ?
C3 N1 C2 117.8(3) . . ?
C3 N1 I1 119.6(3) . . ?
C2 N1 I1 122.3(2) . . ?
C5 N2 C7 120.7(3) . . ?
C5 N2 C6 120.4(3) . . ?
C7 N2 C6 117.1(3) . . ?
C9 N3 C10 117.7(3) . . ?
C9 N3 I1 121.3(2) . . ?
C10 N3 I1 120.9(2) . . ?
C12 N4 C13 120.7(3) . . ?
C12 N4 C14 121.4(3) . . ?
C13 N4 C14 117.8(3) . . ?
C2 C1 C5 120.5(4) . . ?
C2 C1 H1 119.7 . . ?
C5 C1 H1 119.7 . . ?
N1 C2 C1 122.6(4) . . ?
N1 C2 H2 118.7 . . ?
C1 C2 H2 118.7 . . ?
N1 C3 C4 123.1(4) . . ?
N1 C3 H3 118.4 . . ?
C4 C3 H3 118.4 . . ?
C3 C4 C5 120.0(4) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
N2 C5 C4 122.2(3) . . ?
N2 C5 C1 121.8(3) . . ?
C4 C5 C1 116.0(3) . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C12 119.7(3) . . ?
C9 C8 H8 120.1 . . ?
C12 C8 H8 120.1 . . ?
N3 C9 C8 123.2(4) . . ?
N3 C9 H9 118.4 . . ?
C8 C9 H9 118.4 . . ?
N3 C10 C11 123.3(4) . . ?
N3 C10 H10 118.4 . . ?
C11 C10 H10 118.4 . . ?
C10 C11 C12 119.7(4) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
N4 C12 C8 121.9(3) . . ?
N4 C12 C11 121.8(3) . . ?
C8 C12 C11 116.3(3) . . ?
N4 C13 H13A 109.5 . . ?
N4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 S1 O1 113.55(15) . . ?
O2 S1 N5 112.29(16) . . ?
O1 S1 N5 111.86(16) . . ?
O2 S1 C15 110.19(17) . . ?
O1 S1 C15 110.28(16) . . ?
N5 S1 C15 97.56(16) . . ?
C21 N5 S1 111.3(2) . . ?
C16 C15 C20 122.6(3) . . ?
C16 C15 S1 131.3(3) . . ?
C20 C15 S1 106.1(3) . . ?
C15 C16 C17 117.2(4) . . ?
C15 C16 H16 121.4 . . ?
C17 C16 H16 121.4 . . ?
C18 C17 C16 121.1(4) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 121.1(4) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C18 C19 C20 118.2(4) . . ?
C18 C19 H19 120.9 . . ?
C20 C19 H19 120.9 . . ?
C15 C20 C19 119.8(3) . . ?
C15 C20 C21 112.2(3) . . ?
C19 C20 C21 128.0(3) . . ?
O3 C21 N5 124.4(3) . . ?
O3 C21 C20 122.7(3) . . ?
N5 C21 C20 112.8(3) . . ?

_refine_diff_density_max         0.353
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.090



####################################################################### 
# 
# 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_4a_1
_database_code_depnum_ccdc_archive 'CCDC 2255945'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        OID-009-3
_chemical_name_common            (NISac+DMAP)+DMAP
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 I N4, C7 H4 N O3 S'
_chemical_formula_sum            'C21 H24 I N5 O3 S'
_chemical_formula_weight         553.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   16.2893(14)
_cell_length_b                   7.8087(7)
_cell_length_c                   19.0946(19)
_cell_angle_alpha                90
_cell_angle_beta                 109.270(3)
_cell_angle_gamma                90
_cell_volume                     2292.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    3722
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      28.283

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    1.520
_shelx_estimated_absorpt_T_min   0.741
_shelx_estimated_absorpt_T_max   0.875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4332
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13217
_diffrn_reflns_av_unetI/netI     0.2828
_diffrn_reflns_av_R_equivalents  0.1620
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.210
_diffrn_reflns_theta_max         25.247
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             4115
_reflns_number_gt                1353
_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0202P)²] 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         4115
_refine_ls_number_parameters     304
_refine_ls_number_restraints     99
_refine_ls_R_factor_all          0.2721
_refine_ls_R_factor_gt           0.0922
_refine_ls_wR_factor_ref         0.1805
_refine_ls_wR_factor_gt          0.1401
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      0.999
_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 0.48996(5) 0.25117(16) 0.47452(6) 0.0592(4) Uani 1 1 d . . . . .
N1 N 0.6255(7) 0.1454(12) 0.5010(7) 0.047(3) Uani 1 1 d . . . . .
N2 N 0.8708(8) -0.0680(14) 0.5526(8) 0.063(4) Uani 1 1 d . . . . .
N3 N 0.3530(9) 0.3511(13) 0.4446(9) 0.056(4) Uani 1 1 d . . . . .
N4 N 0.1013(9) 0.5374(16) 0.3882(9) 0.067(4) Uani 1 1 d . . . . .
C1 C 0.7330(9) 0.0055(14) 0.4657(9) 0.050(4) Uani 1 1 d . . . . .
H1 H 0.750908 -0.041374 0.427100 0.060 Uiso 1 1 calc R U . . .
C2 C 0.6521(9) 0.0749(16) 0.4467(8) 0.050(4) Uani 1 1 d . . . . .
H2 H 0.614678 0.074361 0.396586 0.060 Uiso 1 1 calc R U . . .
C3 C 0.6791(9) 0.1453(14) 0.5704(9) 0.051(4) Uani 1 1 d . . . . .
H3 H 0.659825 0.195648 0.607531 0.061 Uiso 1 1 calc R U . . .
C4 C 0.7600(9) 0.0770(15) 0.5911(9) 0.048(4) Uani 1 1 d . . . . .
H4 H 0.796032 0.081542 0.641613 0.058 Uiso 1 1 calc R U . . .
C5 C 0.7915(10) -0.0016(16) 0.5378(11) 0.048(4) Uani 1 1 d . . . . .
C6 C 0.9012(9) -0.1370(16) 0.4966(9) 0.071(5) Uani 1 1 d . . . . .
H6A H 0.866585 -0.238018 0.474532 0.107 Uiso 1 1 calc R U . . .
H6B H 0.962418 -0.169829 0.518568 0.107 Uiso 1 1 calc R U . . .
H6C H 0.895467 -0.050575 0.458018 0.107 Uiso 1 1 calc R U . . .
C7 C 0.9292(9) -0.0710(18) 0.6289(9) 0.067(5) Uani 1 1 d . . . . .
H7A H 0.956119 0.041981 0.642087 0.101 Uiso 1 1 calc R U . . .
H7B H 0.974634 -0.157022 0.633922 0.101 Uiso 1 1 calc R U . . .
H7C H 0.896396 -0.099850 0.661976 0.101 Uiso 1 1 calc R U . . .
C8 C 0.2401(11) 0.4784(15) 0.4835(10) 0.057(5) Uani 1 1 d . . . . .
H8 H 0.221063 0.519124 0.522407 0.069 Uiso 1 1 calc R U . . .
C9 C 0.3251(10) 0.4105(15) 0.4989(9) 0.050(4) Uani 1 1 d . . . . .
H9 H 0.363224 0.407080 0.548781 0.060 Uiso 1 1 calc R U . . .
C10 C 0.3003(10) 0.3521(15) 0.3770(10) 0.054(5) Uani 1 1 d . . . . .
H10 H 0.320689 0.307023 0.339610 0.064 Uiso 1 1 calc R U . . .
C11 C 0.2177(12) 0.4132(18) 0.3560(10) 0.067(5) Uani 1 1 d . . . . .
H11 H 0.182562 0.407536 0.305264 0.081 Uiso 1 1 calc R U . . .
C12 C 0.1834(12) 0.4842(18) 0.4076(12) 0.059(6) Uani 1 1 d . . . . .
C13 C 0.0465(11) 0.545(2) 0.3107(11) 0.097(7) Uani 1 1 d . . . . .
H13A H 0.064182 0.642371 0.286591 0.146 Uiso 1 1 calc R U . . .
H13B H -0.014342 0.559183 0.307708 0.146 Uiso 1 1 calc R U . . .
H13C H 0.052811 0.438734 0.285705 0.146 Uiso 1 1 calc R U . . .
C14 C 0.0646(9) 0.6055(17) 0.4449(9) 0.064(5) Uani 1 1 d . . . . .
H14A H 0.090966 0.544874 0.491982 0.096 Uiso 1 1 calc R U . . .
H14B H 0.001501 0.587993 0.427772 0.096 Uiso 1 1 calc R U . . .
H14C H 0.077360 0.728099 0.452238 0.096 Uiso 1 1 calc R U . . .
S1 S 0.1745(3) 0.8541(6) 0.1746(4) 0.061(2) Uani 0.776(8) 1 d D . P A 1
O1 O 0.1384(9) 0.767(2) 0.1033(7) 0.083(5) Uani 0.776(8) 1 d D . P A 1
O2 O 0.1269(7) 0.8292(13) 0.2267(7) 0.065(5) Uani 0.776(8) 1 d D . P A 1
O3 O 0.3044(11) 1.245(2) 0.1969(10) 0.107(6) Uani 0.776(8) 1 d D . P A 1
N5 N 0.1886(11) 1.0538(17) 0.1607(12) 0.078(6) Uani 0.776(8) 1 d D . P A 1
C21 C 0.2733(13) 1.0972(19) 0.1944(15) 0.054(9) Uani 0.776(8) 1 d D . P A 1
S1B S 0.2447(17) 1.094(2) 0.1880(19) 0.054(7) Uiso 0.224(8) 1 d D U P A 2
O1B O 0.286(3) 1.210(6) 0.150(3) 0.054(7) Uiso 0.224(8) 1 d D U P A 2
O2B O 0.227(3) 1.191(4) 0.247(2) 0.054(7) Uiso 0.224(8) 1 d D U P A 2
O3B O 0.133(3) 0.704(5) 0.135(3) 0.054(7) Uiso 0.224(8) 1 d D U P A 2
N5B N 0.1686(18) 0.968(4) 0.149(3) 0.054(7) Uiso 0.224(8) 1 d D U P A 2
C21B C 0.1915(15) 0.803(4) 0.1644(16) 0.054(7) Uiso 0.224(8) 1 d D U P A 2
C15 C 0.2840(7) 0.7941(12) 0.2180(7) 0.042(4) Uani 1 1 d D . . . .
C16 C 0.3249(9) 0.6412(17) 0.2396(8) 0.051(5) Uani 1 1 d . . . . .
H16 H 0.293339 0.537258 0.225741 0.062 Uiso 1 1 calc R U . . .
C17 C 0.4105(10) 0.6369(19) 0.2809(9) 0.060(5) Uani 1 1 d . . . . .
H17 H 0.438935 0.532567 0.300334 0.072 Uiso 1 1 calc R U . . .
C18 C 0.4544(11) 0.7909(18) 0.2933(9) 0.072(5) Uani 1 1 d . . . . .
H18 H 0.514701 0.790154 0.321050 0.086 Uiso 1 1 calc R U . . .
C19 C 0.4149(11) 0.949(2) 0.2671(10) 0.077(6) Uani 1 1 d . . . . .
H19 H 0.447403 1.052396 0.275217 0.093 Uiso 1 1 calc R U . . .
C20 C 0.3284(9) 0.9470(16) 0.2299(8) 0.054(5) Uani 1 1 d 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 N1 2.253(11) . ?
I1 N3 2.252(13) . ?
N1 C3 1.325(16) . ?
N1 C2 1.363(16) . ?
N2 C5 1.332(18) . ?
N2 C6 1.425(18) . ?
N2 C7 1.453(16) . ?
N3 C10 1.293(17) . ?
N3 C9 1.343(18) . ?
N4 C12 1.332(19) . ?
N4 C13 1.455(18) . ?
N4 C14 1.497(18) . ?
C1 C2 1.360(17) . ?
C1 C5 1.393(18) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C4 1.355(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.42(2) . ?
C4 H4 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.42(2) . ?
C8 C12 1.44(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.357(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.40(2) . ?
C11 H11 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
S1 O1 1.460(12) . ?
S1 O2 1.462(12) . ?
S1 N5 1.611(13) . ?
S1 C15 1.764(11) . ?
O3 C21 1.252(14) . ?
N5 C21 1.358(16) . ?
C21 C20 1.497(15) . ?
S1B O2B 1.45(2) . ?
S1B O1B 1.46(2) . ?
S1B N5B 1.564(18) . ?
S1B C20 1.760(16) . ?
O3B C21B 1.22(2) . ?
N5B C21B 1.345(18) . ?
C21B C15 1.517(19) . ?
C15 C16 1.363(15) . ?
C15 C20 1.376(14) . ?
C16 C17 1.358(17) . ?
C16 H16 0.9500 . ?
C17 C18 1.379(17) . ?
C17 H17 0.9500 . ?
C18 C19 1.405(18) . ?
C18 H18 0.9500 . ?
C19 C20 1.352(18) . ?
C19 H19 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
N1 I1 N3 178.0(5) . . ?
C3 N1 C2 119.4(13) . . ?
C3 N1 I1 119.9(11) . . ?
C2 N1 I1 120.7(10) . . ?
C5 N2 C6 122.6(16) . . ?
C5 N2 C7 119.2(16) . . ?
C6 N2 C7 118.1(13) . . ?
C10 N3 C9 119.1(15) . . ?
C10 N3 I1 122.1(13) . . ?
C9 N3 I1 118.9(12) . . ?
C12 N4 C13 121.2(17) . . ?
C12 N4 C14 120.9(16) . . ?
C13 N4 C14 117.7(13) . . ?
C2 C1 C5 124.5(17) . . ?
C2 C1 H1 117.8 . . ?
C5 C1 H1 117.8 . . ?
C1 C2 N1 118.8(15) . . ?
C1 C2 H2 120.6 . . ?
N1 C2 H2 120.6 . . ?
N1 C3 C4 123.3(16) . . ?
N1 C3 H3 118.4 . . ?
C4 C3 H3 118.4 . . ?
C3 C4 C5 120.5(16) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
N2 C5 C1 121.7(18) . . ?
N2 C5 C4 124.7(18) . . ?
C1 C5 C4 113.6(16) . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C12 118.6(17) . . ?
C9 C8 H8 120.7 . . ?
C12 C8 H8 120.7 . . ?
N3 C9 C8 121.6(16) . . ?
N3 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
N3 C10 C11 124.4(18) . . ?
N3 C10 H10 117.8 . . ?
C11 C10 H10 117.8 . . ?
C10 C11 C12 121.2(18) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
N4 C12 C11 121.8(19) . . ?
N4 C12 C8 122.8(19) . . ?
C11 C12 C8 115.1(17) . . ?
N4 C13 H13A 109.5 . . ?
N4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 S1 O2 115.6(9) . . ?
O1 S1 N5 109.4(11) . . ?
O2 S1 N5 112.2(9) . . ?
O1 S1 C15 110.4(8) . . ?
O2 S1 C15 109.0(8) . . ?
N5 S1 C15 99.0(7) . . ?
C21 N5 S1 110.0(11) . . ?
O3 C21 N5 125.6(16) . . ?
O3 C21 C20 121.9(17) . . ?
N5 C21 C20 112.5(13) . . ?
O2B S1B O1B 107(3) . . ?
O2B S1B N5B 112(3) . . ?
O1B S1B N5B 125(4) . . ?
O2B S1B C20 108(2) . . ?
O1B S1B C20 103(3) . . ?
N5B S1B C20 100.4(9) . . ?
C21B N5B S1B 112.1(12) . . ?
O3B C21B N5B 113(3) . . ?
O3B C21B C15 137(3) . . ?
N5B C21B C15 109.7(13) . . ?
C16 C15 C20 122.1(12) . . ?
C16 C15 C21B 121.6(15) . . ?
C20 C15 C21B 114.9(11) . . ?
C16 C15 S1 133.8(10) . . ?
C20 C15 S1 104.0(8) . . ?
C17 C16 C15 120.2(14) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 117.0(16) . . ?
C16 C17 H17 121.5 . . ?
C18 C17 H17 121.5 . . ?
C17 C18 C19 123.7(17) . . ?
C17 C18 H18 118.2 . . ?
C19 C18 H18 118.2 . . ?
C20 C19 C18 116.9(16) . . ?
C20 C19 H19 121.6 . . ?
C18 C19 H19 121.6 . . ?
C19 C20 C15 119.8(13) . . ?
C19 C20 C21 126.4(15) . . ?
C15 C20 C21 113.6(12) . . ?
C19 C20 S1B 138.4(15) . . ?
C15 C20 S1B 101.8(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
C5 C1 C2 N1 1(2) . . . . ?
C3 N1 C2 C1 0.4(18) . . . . ?
I1 N1 C2 C1 -177.0(9) . . . . ?
C2 N1 C3 C4 -0.5(19) . . . . ?
I1 N1 C3 C4 176.9(9) . . . . ?
N1 C3 C4 C5 -1(2) . . . . ?
C6 N2 C5 C1 0(2) . . . . ?
C7 N2 C5 C1 179.6(12) . . . . ?
C6 N2 C5 C4 -176.4(13) . . . . ?
C7 N2 C5 C4 4(2) . . . . ?
C2 C1 C5 N2 -178.5(12) . . . . ?
C2 C1 C5 C4 -2(2) . . . . ?
C3 C4 C5 N2 178.2(12) . . . . ?
C3 C4 C5 C1 1.9(19) . . . . ?
C10 N3 C9 C8 -2(2) . . . . ?
I1 N3 C9 C8 178.7(9) . . . . ?
C12 C8 C9 N3 -1(2) . . . . ?
C9 N3 C10 C11 1(2) . . . . ?
I1 N3 C10 C11 -178.9(10) . . . . ?
N3 C10 C11 C12 1(2) . . . . ?
C13 N4 C12 C11 -8(2) . . . . ?
C14 N4 C12 C11 177.1(13) . . . . ?
C13 N4 C12 C8 178.6(13) . . . . ?
C14 N4 C12 C8 4(2) . . . . ?
C10 C11 C12 N4 -176.8(13) . . . . ?
C10 C11 C12 C8 -3(2) . . . . ?
C9 C8 C12 N4 176.4(13) . . . . ?
C9 C8 C12 C11 2.9(19) . . . . ?
O1 S1 N5 C21 -122.6(19) . . . . ?
O2 S1 N5 C21 107.8(19) . . . . ?
C15 S1 N5 C21 -7(2) . . . . ?
S1 N5 C21 O3 -176(3) . . . . ?
S1 N5 C21 C20 3(3) . . . . ?
O2B S1B N5B C21B -110(4) . . . . ?
O1B S1B N5B C21B 118(4) . . . . ?
C20 S1B N5B C21B 4(5) . . . . ?
S1B N5B C21B O3B 180(4) . . . . ?
S1B N5B C21B C15 2(5) . . . . ?
O3B C21B C15 C16 7(3) . . . . ?
N5B C21B C15 C16 -176(3) . . . . ?
O3B C21B C15 C20 174(2) . . . . ?
N5B C21B C15 C20 -10(3) . . . . ?
O1 S1 C15 C16 -57.8(18) . . . . ?
O2 S1 C15 C16 70.2(17) . . . . ?
N5 S1 C15 C16 -172.5(17) . . . . ?
O1 S1 C15 C20 123.4(12) . . . . ?
O2 S1 C15 C20 -108.6(11) . . . . ?
N5 S1 C15 C20 8.7(13) . . . . ?
C20 C15 C16 C17 7(2) . . . . ?
C21B C15 C16 C17 172.6(19) . . . . ?
S1 C15 C16 C17 -171.6(13) . . . . ?
C15 C16 C17 C18 -6(3) . . . . ?
C16 C17 C18 C19 1(3) . . . . ?
C17 C18 C19 C20 2(3) . . . . ?
C18 C19 C20 C15 -1(3) . . . . ?
C18 C19 C20 C21 -177(2) . . . . ?
C18 C19 C20 S1B 178(2) . . . . ?
C16 C15 C20 C19 -3(2) . . . . ?
C21B C15 C20 C19 -169.6(19) . . . . ?
S1 C15 C20 C19 175.8(15) . . . . ?
C16 C15 C20 C21 173.3(18) . . . . ?
S1 C15 C20 C21 -7.8(19) . . . . ?
C16 C15 C20 S1B 177.7(17) . . . . ?
C21B C15 C20 S1B 11(2) . . . . ?
O3 C21 C20 C19 -1(4) . . . . ?
N5 C21 C20 C19 180(2) . . . . ?
O3 C21 C20 C15 -177(2) . . . . ?
N5 C21 C20 C15 3(3) . . . . ?
O2B S1B C20 C19 -71(3) . . . . ?
O1B S1B C20 C19 42(4) . . . . ?
N5B S1B C20 C19 172(3) . . . . ?
O2B S1B C20 C15 108(2) . . . . ?
O1B S1B C20 C15 -139(3) . . . . ?
N5B S1B C20 C15 -9(3) . . . . ?

_refine_diff_density_max         1.220
_refine_diff_density_min         -0.845
_refine_diff_density_rms         0.128



####################################################################### 
# 
# 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_4a_H2O
_database_code_depnum_ccdc_archive 'CCDC 2255947'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        (NISac+4-Iodopyridine)+DMAP
_chemical_name_common            TIM-047
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 I N4, C7 H4 N O3 S, 2(H2 O)'
_chemical_formula_sum            'C21 H28 I N5 O5 S'
_chemical_formula_weight         589.44

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   10.4392(7)
_cell_length_b                   11.0639(7)
_cell_length_c                   11.6234(8)
_cell_angle_alpha                106.974(3)
_cell_angle_beta                 97.528(2)
_cell_angle_gamma                105.542(3)
_cell_volume                     1204.74(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    3457
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      25.682

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_F_000             596
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    1.458
_shelx_estimated_absorpt_T_min   0.694
_shelx_estimated_absorpt_T_max   0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6305
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12339
_diffrn_reflns_av_unetI/netI     0.2016
_diffrn_reflns_av_R_equivalents  0.1169
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.033
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             4182
_reflns_number_gt                2284
_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0569P)²] 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         4182
_refine_ls_number_parameters     314
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.1628
_refine_ls_R_factor_gt           0.0791
_refine_ls_wR_factor_ref         0.1633
_refine_ls_wR_factor_gt          0.1405
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.042
_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 0.74322(8) 0.79056(7) 0.22426(7) 0.0353(3) Uani 1 1 d . . . . .
N1 N 0.5642(8) 0.8404(8) 0.2959(8) 0.032(2) Uani 1 1 d . . . . .
N2 N 0.2288(8) 0.9036(8) 0.4292(7) 0.028(2) Uani 1 1 d . . . . .
N3 N 0.9222(8) 0.7291(8) 0.1661(7) 0.028(2) Uani 1 1 d . . . . .
N4 N 1.2483(8) 0.6011(8) 0.0774(7) 0.030(2) Uani 1 1 d . . . . .
C1 C 0.4024(10) 0.7949(9) 0.4145(9) 0.025(2) Uani 1 1 d . . . . .
H1 H 0.369460 0.748007 0.466966 0.031 Uiso 1 1 calc R U . . .
C2 C 0.5090(11) 0.7758(9) 0.3684(9) 0.030(3) Uani 1 1 d . . . . .
H2 H 0.547641 0.713645 0.387737 0.036 Uiso 1 1 calc R U . . .
C3 C 0.5075(10) 0.9292(10) 0.2687(9) 0.029(2) Uani 1 1 d . . . . .
H3 H 0.545465 0.975920 0.217947 0.034 Uiso 1 1 calc R U . . .
C4 C 0.3994(10) 0.9529(9) 0.3114(9) 0.027(2) Uani 1 1 d . . . . .
H4 H 0.363625 1.016423 0.291205 0.033 Uiso 1 1 calc R U . . .
C5 C 0.3379(10) 0.8831(9) 0.3869(8) 0.024(2) Uani 1 1 d . . . . .
C6 C 0.1686(11) 1.0000(10) 0.4034(10) 0.040(3) Uani 1 1 d . . . . .
H6A H 0.134250 0.973515 0.314127 0.060 Uiso 1 1 calc R U . . .
H6B H 0.237930 1.088557 0.433856 0.060 Uiso 1 1 calc R U . . .
H6C H 0.092976 1.002683 0.444932 0.060 Uiso 1 1 calc R U . . .
C7 C 0.1687(11) 0.8315(11) 0.5063(10) 0.042(3) Uani 1 1 d . . . . .
H7A H 0.159618 0.736920 0.470388 0.064 Uiso 1 1 calc R U . . .
H7B H 0.078380 0.840382 0.510839 0.064 Uiso 1 1 calc R U . . .
H7C H 0.227694 0.868880 0.589584 0.064 Uiso 1 1 calc R U . . .
C8 C 1.1046(10) 0.7371(8) 0.0605(8) 0.023(2) Uani 1 1 d . . . . .
H8 H 1.153548 0.772009 0.007662 0.028 Uiso 1 1 calc R U . . .
C9 C 0.9970(10) 0.7770(9) 0.0923(9) 0.025(2) Uani 1 1 d . . . . .
H9 H 0.973718 0.840866 0.061532 0.030 Uiso 1 1 calc R U . . .
C10 C 0.9559(11) 0.6368(9) 0.2083(9) 0.029(3) Uani 1 1 d . . . . .
H10 H 0.901628 0.599635 0.256845 0.035 Uiso 1 1 calc R U . . .
C11 C 1.0640(10) 0.5956(9) 0.1839(9) 0.027(3) Uani 1 1 d . . . . .
H11 H 1.086347 0.534329 0.219061 0.033 Uiso 1 1 calc R U . . .
C12 C 1.1433(11) 0.6424(10) 0.1072(9) 0.029(3) Uani 1 1 d . . . . .
C13 C 1.2865(12) 0.5050(10) 0.1265(10) 0.041(3) Uani 1 1 d . . . . .
H13A H 1.295511 0.534966 0.216189 0.061 Uiso 1 1 calc R U . . .
H13B H 1.373843 0.498252 0.108110 0.061 Uiso 1 1 calc R U . . .
H13C H 1.215916 0.417391 0.088270 0.061 Uiso 1 1 calc R U . . .
C14 C 1.3262(11) 0.6456(11) -0.0063(10) 0.041(3) Uani 1 1 d . . . . .
H14A H 1.266125 0.615851 -0.088388 0.061 Uiso 1 1 calc R U . . .
H14B H 1.400808 0.607683 -0.012005 0.061 Uiso 1 1 calc R U . . .
H14C H 1.363961 0.743325 0.025097 0.061 Uiso 1 1 calc R U . . .
S1 S 0.2073(2) 0.3698(2) 0.4145(2) 0.0239(6) Uani 1 1 d . . . . .
O1 O 0.2210(7) 0.5071(6) 0.4312(6) 0.0314(17) Uani 1 1 d . . . . .
O2 O 0.2414(7) 0.3470(6) 0.5293(6) 0.0353(18) Uani 1 1 d . . . . .
O3 O -0.0272(6) 0.0958(6) 0.1486(6) 0.0328(17) Uani 1 1 d . . . . .
N5 N 0.0612(8) 0.2724(8) 0.3311(7) 0.029(2) Uani 1 1 d . . . . .
C15 C 0.3047(10) 0.3093(9) 0.3127(8) 0.022(2) Uani 1 1 d . . . . .
C16 C 0.4453(10) 0.3497(10) 0.3183(10) 0.032(3) Uani 1 1 d . . . . .
H16 H 0.506979 0.423300 0.385392 0.039 Uiso 1 1 calc R U . . .
C17 C 0.4898(10) 0.2803(11) 0.2247(11) 0.036(3) Uani 1 1 d . . . . .
H17 H 0.584921 0.305123 0.227535 0.043 Uiso 1 1 calc R U . . .
C18 C 0.4028(10) 0.1753(10) 0.1258(9) 0.030(3) Uani 1 1 d . . . . .
H18 H 0.438725 0.128619 0.062559 0.036 Uiso 1 1 calc R U . . .
C19 C 0.2624(9) 0.1359(9) 0.1166(8) 0.019(2) Uani 1 1 d . . . . .
H19 H 0.201439 0.064198 0.047565 0.023 Uiso 1 1 calc R U . . .
C20 C 0.2144(9) 0.2066(8) 0.2137(8) 0.0183(19) Uani 1 1 d . . . . .
C21 C 0.0700(10) 0.1855(9) 0.2282(9) 0.022(2) Uani 1 1 d . . . . .
O4 O -0.1611(7) 0.3808(7) 0.3184(6) 0.0362(18) Uani 1 1 d D . . . .
H4O H -0.073(4) 0.380(10) 0.332(9) 0.043 Uiso 1 1 d D U . . .
H4P H -0.191(9) 0.423(9) 0.385(6) 0.043 Uiso 1 1 d D U . . .
O5 O -0.2893(7) 0.1118(7) 0.1412(7) 0.0360(18) Uani 1 1 d D . . . .
H5O H -0.259(10) 0.200(4) 0.192(7) 0.043 Uiso 1 1 d D U . . .
H5P H -0.209(5) 0.093(9) 0.144(9) 0.043 Uiso 1 1 d D 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 N3 2.270(8) . ?
I1 N1 2.276(8) . ?
N1 C2 1.346(12) . ?
N1 C3 1.363(12) . ?
N2 C5 1.345(12) . ?
N2 C6 1.455(12) . ?
N2 C7 1.459(12) . ?
N3 C10 1.358(11) . ?
N3 C9 1.360(12) . ?
N4 C12 1.344(12) . ?
N4 C14 1.458(12) . ?
N4 C13 1.462(11) . ?
C1 C2 1.336(14) . ?
C1 C5 1.411(13) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C4 1.348(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.434(13) . ?
C4 H4 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.368(13) . ?
C8 C12 1.434(13) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.359(14) . ?
C10 H10 0.9500 . ?
C11 C12 1.408(14) . ?
C11 H11 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
S1 O1 1.440(6) . ?
S1 O2 1.446(6) . ?
S1 N5 1.596(8) . ?
S1 C15 1.760(10) . ?
O3 C21 1.244(11) . ?
N5 C21 1.330(12) . ?
C15 C20 1.372(12) . ?
C15 C16 1.402(13) . ?
C16 C17 1.352(14) . ?
C16 H16 0.9500 . ?
C17 C18 1.370(14) . ?
C17 H17 0.9500 . ?
C18 C19 1.392(13) . ?
C18 H18 0.9500 . ?
C19 C20 1.407(12) . ?
C19 H19 0.9500 . ?
C20 C21 1.502(13) . ?
O4 H4O 0.91(2) . ?
O4 H4P 0.92(2) . ?
O5 H5O 0.92(2) . ?
O5 H5P 0.92(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 I1 N1 174.2(3) . . ?
C2 N1 C3 117.7(9) . . ?
C2 N1 I1 117.6(7) . . ?
C3 N1 I1 124.6(7) . . ?
C5 N2 C6 122.0(8) . . ?
C5 N2 C7 120.6(8) . . ?
C6 N2 C7 117.5(9) . . ?
C10 N3 C9 118.0(9) . . ?
C10 N3 I1 117.0(7) . . ?
C9 N3 I1 125.0(6) . . ?
C12 N4 C14 122.6(8) . . ?
C12 N4 C13 120.3(8) . . ?
C14 N4 C13 117.1(8) . . ?
C2 C1 C5 121.3(9) . . ?
C2 C1 H1 119.3 . . ?
C5 C1 H1 119.3 . . ?
C1 C2 N1 123.3(9) . . ?
C1 C2 H2 118.4 . . ?
N1 C2 H2 118.4 . . ?
C4 C3 N1 122.3(9) . . ?
C4 C3 H3 118.9 . . ?
N1 C3 H3 118.9 . . ?
C3 C4 C5 120.6(9) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
N2 C5 C1 123.5(9) . . ?
N2 C5 C4 121.8(9) . . ?
C1 C5 C4 114.7(9) . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C12 119.8(9) . . ?
C9 C8 H8 120.1 . . ?
C12 C8 H8 120.1 . . ?
N3 C9 C8 122.6(9) . . ?
N3 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?
N3 C10 C11 122.7(10) . . ?
N3 C10 H10 118.7 . . ?
C11 C10 H10 118.7 . . ?
C10 C11 C12 120.9(9) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
N4 C12 C11 122.9(9) . . ?
N4 C12 C8 121.2(9) . . ?
C11 C12 C8 115.9(9) . . ?
N4 C13 H13A 109.5 . . ?
N4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 S1 O2 113.2(4) . . ?
O1 S1 N5 111.3(4) . . ?
O2 S1 N5 113.1(4) . . ?
O1 S1 C15 111.5(4) . . ?
O2 S1 C15 109.8(4) . . ?
N5 S1 C15 96.8(4) . . ?
C21 N5 S1 112.5(7) . . ?
C20 C15 C16 121.5(9) . . ?
C20 C15 S1 106.7(7) . . ?
C16 C15 S1 131.8(8) . . ?
C17 C16 C15 117.6(10) . . ?
C17 C16 H16 121.2 . . ?
C15 C16 H16 121.2 . . ?
C16 C17 C18 122.4(10) . . ?
C16 C17 H17 118.8 . . ?
C18 C17 H17 118.8 . . ?
C17 C18 C19 121.0(10) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C18 C19 C20 117.3(9) . . ?
C18 C19 H19 121.3 . . ?
C20 C19 H19 121.3 . . ?
C15 C20 C19 120.2(9) . . ?
C15 C20 C21 111.2(8) . . ?
C19 C20 C21 128.6(8) . . ?
O3 C21 N5 126.1(9) . . ?
O3 C21 C20 121.2(9) . . ?
N5 C21 C20 112.7(8) . . ?
H4O O4 H4P 118(9) . . ?
H5O O5 H5P 101(9) . . ?

_refine_diff_density_max         1.125
_refine_diff_density_min         -0.785
_refine_diff_density_rms         0.170



####################################################################### 
# 
# 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_4ab
_database_code_depnum_ccdc_archive 'CCDC 2255948'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        THY-507
_chemical_name_common            (NISac+DMAP)+4-Pyrrolidinopyridine
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H22 I N4, C7 H4 N O3 S, C H2 Cl2'
_chemical_formula_sum            'C24 H28 Cl2 I N5 O3 S'
_chemical_formula_weight         664.37

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.1076(6)
_cell_length_b                   10.3354(9)
_cell_length_c                   17.7279(14)
_cell_angle_alpha                75.849(2)
_cell_angle_beta                 84.311(2)
_cell_angle_gamma                68.5060(10)
_cell_volume                     1340.19(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1867
_cell_measurement_theta_min      2.3770
_cell_measurement_theta_max      23.1430

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_F_000             668
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    1.508
_shelx_estimated_absorpt_T_min   0.704
_shelx_estimated_absorpt_T_max   0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97366
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.891
_oxdiff_exptl_absorpt_empirical_full_max 1.169
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7359
_diffrn_reflns_av_unetI/netI     0.1456
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.173
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4837
_reflns_number_gt                3269
_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       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0561P)²+2.8911P] 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         4837
_refine_ls_number_parameters     327
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1160
_refine_ls_R_factor_gt           0.0778
_refine_ls_wR_factor_ref         0.1915
_refine_ls_wR_factor_gt          0.1704
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.069
_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 0.26685(8) 0.46410(8) 0.49103(4) 0.0312(2) Uani 1 1 d . . . . .
N1 N 0.1345(10) 0.5692(9) 0.3743(5) 0.033(2) Uani 1 1 d . . . . .
N2 N -0.1444(12) 0.7701(9) 0.1683(5) 0.041(2) Uani 1 1 d . . . . .
N3 N 0.3948(10) 0.3649(9) 0.6078(5) 0.032(2) Uani 1 1 d . . . . .
N4 N 0.6489(11) 0.1920(9) 0.8201(5) 0.032(2) Uani 1 1 d . . . . .
C1 C 0.0508(12) 0.5581(10) 0.2522(6) 0.028(2) Uani 1 1 d . . . . .
H1 H 0.058514 0.502074 0.215858 0.034 Uiso 1 1 calc R U . . .
C2 C 0.1419(12) 0.4976(10) 0.3194(6) 0.027(2) Uani 1 1 d . . . . .
H2 H 0.214854 0.399551 0.328234 0.032 Uiso 1 1 calc R U . . .
C4 C -0.0626(14) 0.7803(11) 0.2944(6) 0.034(3) Uani 1 1 d . . . . .
H4 H -0.130606 0.879275 0.286582 0.041 Uiso 1 1 calc R U . . .
C5 C -0.0552(13) 0.7037(11) 0.2359(6) 0.030(3) Uani 1 1 d . . . . .
C3 C 0.0282(14) 0.7097(11) 0.3606(7) 0.037(3) Uani 1 1 d . . . . .
H3 H 0.017650 0.760368 0.399932 0.044 Uiso 1 1 calc R U . . .
C6 C -0.1418(17) 0.6925(12) 0.1094(7) 0.050(3) Uani 1 1 d . . . . .
H6A H -0.018906 0.645035 0.094055 0.075 Uiso 1 1 calc R U . . .
H6B H -0.208079 0.759368 0.063828 0.075 Uiso 1 1 calc R U . . .
H6C H -0.196621 0.620793 0.130754 0.075 Uiso 1 1 calc R U . . .
C7 C -0.2583(16) 0.9216(12) 0.1486(7) 0.055(4) Uani 1 1 d . . . . .
H7A H -0.363788 0.937353 0.182351 0.082 Uiso 1 1 calc R U . . .
H7B H -0.294415 0.948008 0.094134 0.082 Uiso 1 1 calc R U . . .
H7C H -0.192635 0.980290 0.156130 0.082 Uiso 1 1 calc R U . . .
C8 C 0.4639(12) 0.3951(11) 0.7299(6) 0.030(3) Uani 1 1 d . . . . .
H8 H 0.447506 0.456710 0.764190 0.036 Uiso 1 1 calc R U . . .
C9 C 0.3900(13) 0.4473(11) 0.6585(6) 0.031(3) Uani 1 1 d . . . . .
H9 H 0.331032 0.547537 0.642560 0.038 Uiso 1 1 calc R U . . .
C10 C 0.4864(13) 0.2257(11) 0.6301(7) 0.035(3) Uani 1 1 d . . . . .
H10 H 0.493014 0.166068 0.595907 0.042 Uiso 1 1 calc R U . . .
C11 C 0.5712(12) 0.1646(11) 0.6997(6) 0.030(2) Uani 1 1 d . . . . .
H11 H 0.634590 0.064595 0.712366 0.036 Uiso 1 1 calc R U . . .
C12 C 0.5667(12) 0.2468(11) 0.7534(6) 0.025(2) Uani 1 1 d . . . . .
C13 C 0.6460(14) 0.2746(12) 0.8763(6) 0.043(3) Uani 1 1 d D . . . .
H13A H 0.526838 0.309536 0.900134 0.052 Uiso 1 1 calc R U . . .
H13B H 0.683216 0.356788 0.852140 0.052 Uiso 1 1 calc R U . . .
C14 C 0.783(2) 0.1630(14) 0.9369(9) 0.080(4) Uani 1 1 d D . . . .
H14A H 0.746597 0.177668 0.990047 0.096 Uiso 1 1 calc R U . . .
H14B H 0.901685 0.169557 0.925186 0.096 Uiso 1 1 calc R U . . .
C15 C 0.783(2) 0.0142(15) 0.9292(8) 0.084(4) Uani 1 1 d D . . . .
H15A H 0.896921 -0.063137 0.946550 0.101 Uiso 1 1 calc R U . . .
H15B H 0.684567 -0.009500 0.959317 0.101 Uiso 1 1 calc R U . . .
C16 C 0.7585(14) 0.0400(12) 0.8425(7) 0.048(3) Uani 1 1 d D . . . .
H16A H 0.874011 0.019607 0.814646 0.057 Uiso 1 1 calc R U . . .
H16B H 0.697410 -0.020363 0.831321 0.057 Uiso 1 1 calc R U . . .
S1 S 0.6003(3) 0.6887(3) 0.88771(16) 0.0287(6) Uani 1 1 d . . . . .
O1 O 0.5734(9) 0.7772(8) 0.9424(4) 0.0368(18) Uani 1 1 d . . . . .
O2 O 0.7191(8) 0.5430(7) 0.9141(4) 0.0360(19) Uani 1 1 d . . . . .
O3 O 0.5444(9) 0.8544(8) 0.6803(4) 0.0379(19) Uani 1 1 d . . . . .
N5 N 0.6599(10) 0.7596(9) 0.8048(5) 0.029(2) Uani 1 1 d . . . . .
C17 C 0.3953(11) 0.6931(10) 0.8597(6) 0.023(2) Uani 1 1 d . . . . .
C18 C 0.2666(13) 0.6490(11) 0.9038(6) 0.032(3) Uani 1 1 d . . . . .
H18 H 0.280978 0.604360 0.957563 0.038 Uiso 1 1 calc R U . . .
C19 C 0.1098(14) 0.6755(11) 0.8622(7) 0.039(3) Uani 1 1 d . . . . .
H19 H 0.015381 0.649704 0.889413 0.046 Uiso 1 1 calc R U . . .
C20 C 0.0933(12) 0.7373(11) 0.7841(6) 0.030(2) Uani 1 1 d . . . . .
H20 H -0.011035 0.751336 0.758153 0.036 Uiso 1 1 calc R U . . .
C21 C 0.2252(13) 0.7794(10) 0.7426(6) 0.030(2) Uani 1 1 d . . . . .
H21 H 0.212681 0.822244 0.688572 0.036 Uiso 1 1 calc R U . . .
C22 C 0.3739(12) 0.7579(10) 0.7809(6) 0.028(2) Uani 1 1 d . . . . .
C23 C 0.5363(12) 0.7949(10) 0.7489(6) 0.027(2) Uani 1 1 d . . . . .
Cl1 Cl 0.2917(4) 0.9928(3) 0.53982(18) 0.0496(8) Uani 1 1 d . . . . .
Cl2 Cl 0.0092(4) 1.2097(3) 0.44004(18) 0.0480(8) Uani 1 1 d . . . . .
C24 C 0.1963(18) 1.0538(12) 0.4451(7) 0.059(4) Uani 1 1 d . . . . .
H24A H 0.285299 1.072923 0.405899 0.071 Uiso 1 1 calc R U . . .
H24B H 0.162211 0.978535 0.432990 0.071 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 N3 2.240(9) . ?
I1 N1 2.258(9) . ?
N1 C2 1.345(13) . ?
N1 C3 1.365(13) . ?
N2 C5 1.355(13) . ?
N2 C6 1.458(14) . ?
N2 C7 1.471(13) . ?
N3 C10 1.332(12) . ?
N3 C9 1.372(13) . ?
N4 C12 1.309(12) . ?
N4 C13 1.457(13) . ?
N4 C16 1.469(12) . ?
C1 C2 1.352(13) . ?
C1 C5 1.406(13) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C4 C3 1.345(14) . ?
C4 C5 1.436(14) . ?
C4 H4 0.9500 . ?
C3 H3 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.353(14) . ?
C8 C12 1.427(13) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.366(14) . ?
C10 H10 0.9500 . ?
C11 C12 1.413(14) . ?
C11 H11 0.9500 . ?
C13 C14 1.550(13) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.575(14) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.514(14) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
S1 O1 1.439(7) . ?
S1 O2 1.448(7) . ?
S1 N5 1.588(9) . ?
S1 C17 1.763(9) . ?
O3 C23 1.229(12) . ?
N5 C23 1.368(13) . ?
C17 C18 1.386(13) . ?
C17 C22 1.391(14) . ?
C18 C19 1.438(15) . ?
C18 H18 0.9500 . ?
C19 C20 1.373(14) . ?
C19 H19 0.9500 . ?
C20 C21 1.379(14) . ?
C20 H20 0.9500 . ?
C21 C22 1.363(14) . ?
C21 H21 0.9500 . ?
C22 C23 1.522(12) . ?
Cl1 C24 1.788(13) . ?
Cl2 C24 1.753(12) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 I1 N1 178.6(3) . . ?
C2 N1 C3 117.3(9) . . ?
C2 N1 I1 123.4(7) . . ?
C3 N1 I1 119.0(8) . . ?
C5 N2 C6 121.6(9) . . ?
C5 N2 C7 124.6(10) . . ?
C6 N2 C7 113.8(10) . . ?
C10 N3 C9 116.5(9) . . ?
C10 N3 I1 122.5(8) . . ?
C9 N3 I1 120.9(7) . . ?
C12 N4 C13 123.9(9) . . ?
C12 N4 C16 121.6(9) . . ?
C13 N4 C16 114.5(9) . . ?
C2 C1 C5 120.2(10) . . ?
C2 C1 H1 119.9 . . ?
C5 C1 H1 119.9 . . ?
N1 C2 C1 123.3(9) . . ?
N1 C2 H2 118.4 . . ?
C1 C2 H2 118.4 . . ?
C3 C4 C5 119.0(10) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N2 C5 C1 122.3(10) . . ?
N2 C5 C4 121.2(10) . . ?
C1 C5 C4 116.4(10) . . ?
C4 C3 N1 123.6(11) . . ?
C4 C3 H3 118.2 . . ?
N1 C3 H3 118.2 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C12 119.5(10) . . ?
C9 C8 H8 120.2 . . ?
C12 C8 H8 120.2 . . ?
C8 C9 N3 124.3(9) . . ?
C8 C9 H9 117.9 . . ?
N3 C9 H9 117.9 . . ?
N3 C10 C11 123.2(10) . . ?
N3 C10 H10 118.4 . . ?
C11 C10 H10 118.4 . . ?
C10 C11 C12 121.4(10) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
N4 C12 C11 122.9(9) . . ?
N4 C12 C8 122.1(10) . . ?
C11 C12 C8 114.9(9) . . ?
N4 C13 C14 101.9(10) . . ?
N4 C13 H13A 111.4 . . ?
C14 C13 H13A 111.4 . . ?
N4 C13 H13B 111.4 . . ?
C14 C13 H13B 111.4 . . ?
H13A C13 H13B 109.3 . . ?
C13 C14 C15 104.9(11) . . ?
C13 C14 H14A 110.8 . . ?
C15 C14 H14A 110.8 . . ?
C13 C14 H14B 110.8 . . ?
C15 C14 H14B 110.8 . . ?
H14A C14 H14B 108.8 . . ?
C16 C15 C14 101.7(11) . . ?
C16 C15 H15A 111.4 . . ?
C14 C15 H15A 111.4 . . ?
C16 C15 H15B 111.4 . . ?
C14 C15 H15B 111.4 . . ?
H15A C15 H15B 109.3 . . ?
N4 C16 C15 103.9(10) . . ?
N4 C16 H16A 111.0 . . ?
C15 C16 H16A 111.0 . . ?
N4 C16 H16B 111.0 . . ?
C15 C16 H16B 111.0 . . ?
H16A C16 H16B 109.0 . . ?
O1 S1 O2 114.4(5) . . ?
O1 S1 N5 111.4(5) . . ?
O2 S1 N5 111.1(4) . . ?
O1 S1 C17 110.4(4) . . ?
O2 S1 C17 110.8(4) . . ?
N5 S1 C17 97.5(4) . . ?
C23 N5 S1 112.3(6) . . ?
C18 C17 C22 122.2(9) . . ?
C18 C17 S1 130.1(8) . . ?
C22 C17 S1 107.7(7) . . ?
C17 C18 C19 115.1(10) . . ?
C17 C18 H18 122.4 . . ?
C19 C18 H18 122.4 . . ?
C20 C19 C18 121.5(10) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C19 C20 C21 121.3(10) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C22 C21 C20 118.4(10) . . ?
C22 C21 H21 120.8 . . ?
C20 C21 H21 120.8 . . ?
C21 C22 C17 121.5(9) . . ?
C21 C22 C23 128.6(10) . . ?
C17 C22 C23 109.9(9) . . ?
O3 C23 N5 126.7(9) . . ?
O3 C23 C22 120.8(10) . . ?
N5 C23 C22 112.5(9) . . ?
Cl2 C24 Cl1 110.9(6) . . ?
Cl2 C24 H24A 109.5 . . ?
Cl1 C24 H24A 109.5 . . ?
Cl2 C24 H24B 109.5 . . ?
Cl1 C24 H24B 109.5 . . ?
H24A C24 H24B 108.0 . . ?

_refine_diff_density_max         1.443
_refine_diff_density_min         -0.785
_refine_diff_density_rms         0.156



####################################################################### 
# 
# 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_4c_3
_database_code_depnum_ccdc_archive 'CCDC 2255953'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        OID-014-2
_chemical_name_common            
(NISac+4-Morpholinopyridine)+4-Pyrrolidinopyridine
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H24 I N4 O2, C7 H4 N O3 S, C H Cl3'
_chemical_formula_sum            'C26 H29 Cl3 I N5 O5 S'
_chemical_formula_weight         756.85

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.3347(4)
_cell_length_b                   10.3539(5)
_cell_length_c                   19.4385(10)
_cell_angle_alpha                76.182(2)
_cell_angle_beta                 87.595(3)
_cell_angle_gamma                66.362(2)
_cell_volume                     1489.53(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    4081
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      27.878

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    1.460
_shelx_estimated_absorpt_T_min   0.789
_shelx_estimated_absorpt_T_max   0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5722
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5391
_diffrn_reflns_av_unetI/netI     0.1139
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.162
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5391
_reflns_number_gt                3507
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0951P)²] 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         5391
_refine_ls_number_parameters     382
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1216
_refine_ls_R_factor_gt           0.0783
_refine_ls_wR_factor_ref         0.1937
_refine_ls_wR_factor_gt          0.1757
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_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 0.25689(8) 0.48971(6) 0.49956(3) 0.0286(2) Uani 1 1 d . . . . .
O1 O 0.6349(12) 0.7130(8) 0.0485(4) 0.060(2) Uani 1 1 d . . . . .
O2 O -0.1059(10) 0.2678(9) 0.9520(4) 0.056(2) Uani 1 1 d . . . . .
N1 N 0.3394(10) 0.5459(8) 0.3883(4) 0.0318(18) Uani 1 1 d . . . . .
N2 N 0.5100(10) 0.6441(7) 0.1855(4) 0.0318(19) Uani 1 1 d . . . . .
N3 N 0.1732(11) 0.4361(8) 0.6107(4) 0.035(2) Uani 1 1 d . . . . .
N4 N -0.0026(10) 0.3364(8) 0.8120(4) 0.0295(18) Uani 1 1 d . . . . .
C1 C 0.4792(13) 0.4680(9) 0.2871(5) 0.032(2) Uani 1 1 d . . . . .
H1 H 0.533623 0.390365 0.264565 0.038 Uiso 1 1 calc R U . . .
C2 C 0.4197(13) 0.4433(9) 0.3523(5) 0.033(2) Uani 1 1 d . . . . .
H2 H 0.435599 0.346406 0.374534 0.040 Uiso 1 1 calc R U . . .
C3 C 0.3196(14) 0.6825(10) 0.3553(5) 0.039(2) Uani 1 1 d . . . . .
H3 H 0.264786 0.757409 0.379484 0.047 Uiso 1 1 calc R U . . .
C4 C 0.3746(14) 0.7179(10) 0.2892(5) 0.036(2) Uani 1 1 d . . . . .
H4 H 0.354477 0.816208 0.268084 0.044 Uiso 1 1 calc R U . . .
C5 C 0.4599(12) 0.6115(9) 0.2522(4) 0.026(2) Uani 1 1 d . . . . .
C6 C 0.6338(13) 0.5311(10) 0.1535(5) 0.035(2) Uani 1 1 d . . . . .
H6A H 0.609899 0.442511 0.168143 0.042 Uiso 1 1 calc R U . . .
H6B H 0.754776 0.506355 0.171190 0.042 Uiso 1 1 calc R U . . .
C7 C 0.6206(17) 0.5793(13) 0.0735(5) 0.056(3) Uani 1 1 d . . . . .
H7A H 0.714694 0.504301 0.054497 0.068 Uiso 1 1 calc R U . . .
H7B H 0.506570 0.587758 0.055552 0.068 Uiso 1 1 calc R U . . .
C8 C 0.4911(15) 0.8185(11) 0.0717(5) 0.044(3) Uani 1 1 d . . . . .
H8A H 0.381172 0.818104 0.054607 0.053 Uiso 1 1 calc R U . . .
H8B H 0.490950 0.915621 0.050757 0.053 Uiso 1 1 calc R U . . .
C9 C 0.4954(14) 0.7926(10) 0.1513(5) 0.037(2) Uani 1 1 d . . . . .
H9A H 0.596631 0.806459 0.168091 0.045 Uiso 1 1 calc R U . . .
H9B H 0.387042 0.864551 0.165264 0.045 Uiso 1 1 calc R U . . .
C10 C 0.0026(13) 0.5131(9) 0.7055(5) 0.036(2) Uani 1 1 d . . . . .
H10 H -0.073723 0.592081 0.723810 0.043 Uiso 1 1 calc R U . . .
C11 C 0.0656(14) 0.5390(10) 0.6417(5) 0.040(3) Uani 1 1 d . . . . .
H11 H 0.031508 0.637524 0.616398 0.049 Uiso 1 1 calc R U . . .
C12 C 0.2212(13) 0.2976(9) 0.6476(5) 0.035(2) Uani 1 1 d . . . . .
H12 H 0.300296 0.222668 0.627527 0.042 Uiso 1 1 calc R U . . .
C13 C 0.1625(14) 0.2594(9) 0.7120(5) 0.036(2) Uani 1 1 d . . . . .
H13 H 0.196390 0.159652 0.734935 0.043 Uiso 1 1 calc R U . . .
C14 C 0.0486(12) 0.3700(9) 0.7458(4) 0.024(2) Uani 1 1 d . . . . .
C15 C -0.1237(13) 0.4494(9) 0.8447(5) 0.034(2) Uani 1 1 d . . . . .
H15A H -0.246030 0.470414 0.830539 0.041 Uiso 1 1 calc R U . . .
H15B H -0.104380 0.539792 0.827390 0.041 Uiso 1 1 calc R U . . .
C16 C -0.0976(14) 0.4031(11) 0.9237(5) 0.046(3) Uani 1 1 d . . . . .
H16A H 0.018245 0.397489 0.937804 0.055 Uiso 1 1 calc R U . . .
H16B H -0.188589 0.477498 0.944153 0.055 Uiso 1 1 calc R U . . .
C17 C 0.0232(16) 0.1637(11) 0.9239(6) 0.053(3) Uani 1 1 d . . . . .
H17A H 0.020911 0.067771 0.945632 0.063 Uiso 1 1 calc R U . . .
H17B H 0.139000 0.159280 0.937178 0.063 Uiso 1 1 calc R U . . .
C18 C 0.0051(14) 0.1906(9) 0.8453(5) 0.036(2) Uani 1 1 d . . . . .
H18A H 0.106405 0.116604 0.828702 0.044 Uiso 1 1 calc R U . . .
H18B H -0.103153 0.182929 0.831488 0.044 Uiso 1 1 calc R U . . .
S1 S 0.5135(3) 0.1770(2) 0.13970(14) 0.0349(6) Uani 1 1 d . . . . .
O3 O 0.4947(10) 0.3227(7) 0.1057(4) 0.052(2) Uani 1 1 d . . . . .
O4 O 0.6190(9) 0.0693(7) 0.1040(4) 0.0475(19) Uani 1 1 d . . . . .
O5 O 0.4641(12) 0.0768(11) 0.3305(4) 0.080(3) Uani 1 1 d . . . . .
N5 N 0.5784(12) 0.1330(9) 0.2222(5) 0.042(2) Uani 1 1 d . . . . .
C19 C 0.3070(12) 0.1701(9) 0.1524(5) 0.029(2) Uani 1 1 d . . . . .
C20 C 0.1707(14) 0.1973(9) 0.1043(6) 0.040(3) Uani 1 1 d . . . . .
H20 H 0.180552 0.224458 0.054564 0.048 Uiso 1 1 calc R U . . .
C21 C 0.0194(11) 0.1831(9) 0.1318(5) 0.027(2) Uani 1 1 d . . . . .
H21 H -0.075136 0.199685 0.100475 0.032 Uiso 1 1 calc R U . . .
C22 C 0.0068(14) 0.1459(10) 0.2028(6) 0.042(3) Uani 1 1 d . . . . .
H22 H -0.097746 0.137593 0.220155 0.050 Uiso 1 1 calc R U . . .
C23 C 0.1365(12) 0.1203(9) 0.2496(6) 0.034(2) Uani 1 1 d . . . . .
H23 H 0.123372 0.094582 0.299150 0.040 Uiso 1 1 calc R U . . .
C24 C 0.2927(13) 0.1322(9) 0.2242(5) 0.033(2) Uani 1 1 d . . . . .
C25 C 0.4536(14) 0.1128(10) 0.2648(5) 0.036(2) Uani 1 1 d . . . . .
Cl1 Cl 0.0981(9) 0.1484(5) 0.5363(4) 0.103(3) Uani 0.681(7) 1 d . . P A 1
Cl2 Cl 0.3473(8) -0.0901(9) 0.4833(4) 0.118(3) Uani 0.681(7) 1 d . . P A 1
Cl3 Cl 0.1667(9) -0.1414(7) 0.6064(4) 0.102(2) Uani 0.681(7) 1 d . . P A 1
C26 C 0.2625(17) -0.0277(11) 0.5563(6) 0.039(4) Uani 0.681(7) 1 d . . P A 1
H26 H 0.359411 -0.030494 0.586023 0.047 Uiso 0.681(7) 1 calc R U P A 1
Cl1B Cl 0.244(2) 0.1222(14) 0.4853(8) 0.099(3) Uiso 0.319(7) 1 d . U P A 2
Cl2B Cl 0.259(2) -0.1779(14) 0.5342(8) 0.099(3) Uiso 0.319(7) 1 d . U P A 2
Cl3B Cl 0.078(2) 0.0271(14) 0.6068(8) 0.099(3) Uiso 0.319(7) 1 d . U P A 2
C26B C 0.2625(17) -0.0277(11) 0.5563(6) 0.099(3) Uiso 0.319(7) 1 d . U P A 2
H26B H 0.371016 -0.057172 0.586778 0.119 Uiso 0.319(7) 1 calc R U P A 2


_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 N3 2.251(7) . ?
I1 N1 2.256(7) . ?
O1 C7 1.404(12) . ?
O1 C8 1.405(12) . ?
O2 C17 1.385(12) . ?
O2 C16 1.406(12) . ?
N1 C2 1.345(11) . ?
N1 C3 1.351(11) . ?
N2 C5 1.352(10) . ?
N2 C6 1.466(11) . ?
N2 C9 1.480(11) . ?
N3 C11 1.341(12) . ?
N3 C12 1.344(11) . ?
N4 C14 1.349(10) . ?
N4 C15 1.465(11) . ?
N4 C18 1.470(10) . ?
C1 C2 1.345(12) . ?
C1 C5 1.425(11) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C4 1.362(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(12) . ?
C4 H4 0.9500 . ?
C6 C7 1.509(13) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.506(13) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.337(12) . ?
C10 C14 1.404(11) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.351(12) . ?
C12 H12 0.9500 . ?
C13 C14 1.442(12) . ?
C13 H13 0.9500 . ?
C15 C16 1.492(13) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.489(13) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
S1 O4 1.425(7) . ?
S1 O3 1.442(6) . ?
S1 N5 1.611(9) . ?
S1 C19 1.756(10) . ?
O5 C25 1.237(11) . ?
N5 C25 1.354(12) . ?
C19 C24 1.371(12) . ?
C19 C20 1.397(13) . ?
C20 C21 1.397(13) . ?
C20 H20 0.9500 . ?
C21 C22 1.352(13) . ?
C21 H21 0.9500 . ?
C22 C23 1.344(14) . ?
C22 H22 0.9500 . ?
C23 C24 1.414(12) . ?
C23 H23 0.9500 . ?
C24 C25 1.503(13) . ?
Cl1 C26 1.748(12) . ?
Cl2 C26 1.709(13) . ?
Cl3 C26 1.764(12) . ?
C26 H26 1.0000 . ?
Cl1B C26B 1.772(17) . ?
Cl2B C26B 1.719(17) . ?
Cl3B C26B 1.759(18) . ?
C26B H26B 1.0000 . ?

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
N3 I1 N1 179.4(3) . . ?
C7 O1 C8 107.3(8) . . ?
C17 O2 C16 108.8(7) . . ?
C2 N1 C3 116.2(8) . . ?
C2 N1 I1 121.6(6) . . ?
C3 N1 I1 122.1(6) . . ?
C5 N2 C6 121.4(7) . . ?
C5 N2 C9 121.2(7) . . ?
C6 N2 C9 114.1(7) . . ?
C11 N3 C12 116.6(8) . . ?
C11 N3 I1 122.2(6) . . ?
C12 N3 I1 121.1(6) . . ?
C14 N4 C15 121.2(7) . . ?
C14 N4 C18 122.1(7) . . ?
C15 N4 C18 113.4(7) . . ?
C2 C1 C5 119.4(8) . . ?
C2 C1 H1 120.3 . . ?
C5 C1 H1 120.3 . . ?
C1 C2 N1 124.8(8) . . ?
C1 C2 H2 117.6 . . ?
N1 C2 H2 117.6 . . ?
N1 C3 C4 123.2(9) . . ?
N1 C3 H3 118.4 . . ?
C4 C3 H3 118.4 . . ?
C3 C4 C5 120.8(8) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
N2 C5 C4 122.1(8) . . ?
N2 C5 C1 122.1(7) . . ?
C4 C5 C1 115.7(8) . . ?
N2 C6 C7 111.9(8) . . ?
N2 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
N2 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
O1 C7 C6 112.8(8) . . ?
O1 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
O1 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
O1 C8 C9 112.4(9) . . ?
O1 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
O1 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
N2 C9 C8 111.2(7) . . ?
N2 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
N2 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C14 120.5(8) . . ?
C11 C10 H10 119.8 . . ?
C14 C10 H10 119.8 . . ?
C10 C11 N3 124.8(9) . . ?
C10 C11 H11 117.6 . . ?
N3 C11 H11 117.6 . . ?
N3 C12 C13 123.4(8) . . ?
N3 C12 H12 118.3 . . ?
C13 C12 H12 118.3 . . ?
C12 C13 C14 120.1(8) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
N4 C14 C10 123.5(8) . . ?
N4 C14 C13 121.8(7) . . ?
C10 C14 C13 114.7(8) . . ?
N4 C15 C16 111.1(8) . . ?
N4 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
N4 C15 H15B 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
O2 C16 C15 112.9(8) . . ?
O2 C16 H16A 109.0 . . ?
C15 C16 H16A 109.0 . . ?
O2 C16 H16B 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
O2 C17 C18 114.3(10) . . ?
O2 C17 H17A 108.7 . . ?
C18 C17 H17A 108.7 . . ?
O2 C17 H17B 108.7 . . ?
C18 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
N4 C18 C17 109.6(8) . . ?
N4 C18 H18A 109.8 . . ?
C17 C18 H18A 109.8 . . ?
N4 C18 H18B 109.8 . . ?
C17 C18 H18B 109.8 . . ?
H18A C18 H18B 108.2 . . ?
O4 S1 O3 114.5(4) . . ?
O4 S1 N5 111.4(5) . . ?
O3 S1 N5 111.5(4) . . ?
O4 S1 C19 110.0(4) . . ?
O3 S1 C19 110.6(4) . . ?
N5 S1 C19 97.5(4) . . ?
C25 N5 S1 111.1(7) . . ?
C24 C19 C20 121.3(9) . . ?
C24 C19 S1 107.0(7) . . ?
C20 C19 S1 131.7(8) . . ?
C21 C20 C19 117.8(10) . . ?
C21 C20 H20 121.1 . . ?
C19 C20 H20 121.1 . . ?
C22 C21 C20 120.3(9) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C23 C22 C21 122.5(10) . . ?
C23 C22 H22 118.7 . . ?
C21 C22 H22 118.7 . . ?
C22 C23 C24 119.2(10) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C19 C24 C23 118.9(9) . . ?
C19 C24 C25 111.4(9) . . ?
C23 C24 C25 129.6(9) . . ?
O5 C25 N5 126.8(10) . . ?
O5 C25 C24 120.2(10) . . ?
N5 C25 C24 112.9(8) . . ?
Cl2 C26 Cl1 113.9(7) . . ?
Cl2 C26 Cl3 109.1(7) . . ?
Cl1 C26 Cl3 106.5(7) . . ?
Cl2 C26 H26 109.1 . . ?
Cl1 C26 H26 109.1 . . ?
Cl3 C26 H26 109.1 . . ?
Cl2B C26B Cl3B 103.5(9) . . ?
Cl2B C26B Cl1B 116.9(9) . . ?
Cl3B C26B Cl1B 108.1(9) . . ?
Cl2B C26B H26B 109.4 . . ?
Cl3B C26B H26B 109.4 . . ?
Cl1B C26B H26B 109.4 . . ?

_refine_diff_density_max         1.250
_refine_diff_density_min         -1.533
_refine_diff_density_rms         0.307



####################################################################### 
# 
# 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_4bd
_database_code_depnum_ccdc_archive 'CCDC 2255950'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        OID-018-1
_chemical_name_common            
(NISac+4-Piperidinopyridine)+4-Pyrrolidinopyridine)
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H26 I N4, C7 H4 N O3 S, 2(C H2 Cl2)'
_chemical_formula_sum            'C28 H34 Cl4 I N5 O3 S'
_chemical_formula_weight         789.36

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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

_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, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   20.5334(8)
_cell_length_b                   19.1220(7)
_cell_length_c                   8.3713(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.740(2)
_cell_angle_gamma                90
_cell_volume                     3270.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    17097
_cell_measurement_theta_min      4.2890
_cell_measurement_theta_max      73.4930

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_F_000             1592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    11.613
_shelx_estimated_absorpt_T_min   0.175
_shelx_estimated_absorpt_T_max   0.390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.46522
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.678
_oxdiff_exptl_absorpt_empirical_full_max 1.741
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34389
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.625
_diffrn_reflns_theta_max         69.981
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3203
_reflns_number_gt                2631
_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       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0843P)²+4.7813P] 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         3203
_refine_ls_number_parameters     255
_refine_ls_number_restraints     47
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1536
_refine_ls_wR_factor_gt          0.1462
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.073
_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 0.500000 0.22222(2) 0.500000 0.0767(2) Uani 1 2 d S T P . .
N1 N 0.3923(2) 0.2249(2) 0.4150(7) 0.0766(13) Uani 1 1 d . . . . .
N2 N 0.1988(3) 0.2390(3) 0.2299(9) 0.104(2) Uani 0.5 1 d D . P . .
C1 C 0.2924(3) 0.1695(3) 0.3262(8) 0.0776(15) Uani 1 1 d . . . . .
H1 H 0.268865 0.127085 0.307220 0.093 Uiso 1 1 calc R U . . .
C2 C 0.3556(3) 0.1676(3) 0.3843(7) 0.0719(13) Uani 1 1 d . . . . .
H2 H 0.375451 0.123234 0.404819 0.086 Uiso 1 1 calc R U . . .
C3 C 0.3624(3) 0.2875(3) 0.3883(9) 0.0831(18) Uani 1 1 d . . . . .
H3 H 0.387130 0.328782 0.413016 0.100 Uiso 1 1 calc R U . . .
C4 C 0.3000(3) 0.2942(3) 0.3290(9) 0.0774(16) Uani 1 1 d . . . . .
H4 H 0.281828 0.339494 0.310968 0.093 Uiso 1 1 calc R U . . .
C5 C 0.2605(3) 0.2344(3) 0.2927(8) 0.0754(14) Uani 1 1 d . . . . .
C6 C 0.1491(8) 0.1810(8) 0.2275(17) 0.082(4) Uani 0.5 1 d D . P . .
H6A H 0.169056 0.136163 0.265914 0.099 Uiso 0.5 1 calc R U P . .
H6B H 0.112396 0.192843 0.290889 0.099 Uiso 0.5 1 calc R U P . .
C7 C 0.1282(8) 0.1797(8) 0.0505(16) 0.090(4) Uani 0.5 1 d D . P . .
H7A H 0.097420 0.140520 0.024552 0.108 Uiso 0.5 1 calc R U P . .
H7B H 0.166739 0.173039 -0.009935 0.108 Uiso 0.5 1 calc R U P . .
C8 C 0.0952(11) 0.2483(11) 0.004(3) 0.119(9) Uani 0.5 1 d D . P . .
H8A H 0.055550 0.252996 0.061696 0.143 Uiso 0.5 1 calc R U P . .
H8B H 0.081016 0.247759 -0.112259 0.143 Uiso 0.5 1 calc R U P . .
C9 C 0.1385(9) 0.3113(10) 0.0419(16) 0.093(4) Uani 0.5 1 d D . P . .
H9A H 0.176793 0.309956 -0.021304 0.112 Uiso 0.5 1 calc R U P . .
H9B H 0.113928 0.355036 0.016117 0.112 Uiso 0.5 1 calc R U P . .
C10 C 0.1602(8) 0.3074(7) 0.2179(18) 0.077(4) Uani 0.5 1 d D . P . .
H10A H 0.122343 0.305630 0.282215 0.092 Uiso 0.5 1 calc R U P . .
H10B H 0.188305 0.347738 0.253428 0.092 Uiso 0.5 1 calc R U P . .
N3 N 0.1988(3) 0.2390(3) 0.2299(9) 0.104(2) Uani 0.5 1 d D . P . .
C11 C 0.1632(6) 0.1768(6) 0.1502(19) 0.072(3) Uani 0.5 1 d D . P . .
H11A H 0.183447 0.161970 0.053216 0.086 Uiso 0.5 1 calc R U P . .
H11B H 0.162728 0.136799 0.225059 0.086 Uiso 0.5 1 calc R U P . .
C12 C 0.0950(6) 0.2055(7) 0.1072(19) 0.085(4) Uani 0.5 1 d D . P . .
H12A H 0.068884 0.203685 0.200343 0.102 Uiso 0.5 1 calc R U P . .
H12B H 0.071790 0.179248 0.016808 0.102 Uiso 0.5 1 calc R U P . .
C13 C 0.1075(11) 0.2807(10) 0.059(3) 0.115(9) Uani 0.5 1 d D . P . .
H13A H 0.112010 0.283475 -0.057043 0.138 Uiso 0.5 1 calc R U P . .
H13B H 0.070556 0.310893 0.083357 0.138 Uiso 0.5 1 calc R U P . .
C14 C 0.1696(10) 0.3045(8) 0.154(2) 0.084(5) Uani 0.5 1 d D . P . .
H14A H 0.199693 0.325997 0.082583 0.101 Uiso 0.5 1 calc R U P . .
H14B H 0.160228 0.338964 0.236830 0.101 Uiso 0.5 1 calc R U P . .
S1 S 0.31074(9) 0.500000 0.4792(2) 0.0603(4) Uani 1 2 d S T P . .
O1 O 0.3479(2) 0.43678(17) 0.5140(5) 0.0763(10) Uani 1 1 d . . . . .
O2 O 0.1334(3) 0.500000 0.4831(8) 0.0832(16) Uani 1 2 d S T P . .
N4 N 0.2441(3) 0.500000 0.5616(8) 0.0694(15) Uani 1 2 d S T P . .
C15 C 0.2756(3) 0.500000 0.2786(8) 0.0558(14) Uani 1 2 d S T P . .
C16 C 0.3044(4) 0.500000 0.1369(9) 0.0666(17) Uani 1 2 d S T P . .
H16 H 0.350613 0.500000 0.136291 0.080 Uiso 1 2 calc R U P . .
C17 C 0.2625(4) 0.500000 -0.0067(9) 0.0742(19) Uani 1 2 d S T P . .
H17 H 0.280514 0.500000 -0.106928 0.089 Uiso 1 2 calc R U P . .
C18 C 0.1956(4) 0.500000 -0.0028(10) 0.076(2) Uani 1 2 d S T P . .
H18 H 0.168080 0.500000 -0.101122 0.091 Uiso 1 2 calc R U P . .
C19 C 0.1677(4) 0.500000 0.1390(10) 0.0684(18) Uani 1 2 d S T P . .
H19 H 0.121452 0.500000 0.140006 0.082 Uiso 1 2 calc R U P . .
C20 C 0.2088(3) 0.500000 0.2816(8) 0.0575(15) Uani 1 2 d S T P . .
C21 C 0.1914(4) 0.500000 0.4535(9) 0.0650(17) Uani 1 2 d S T P . .
Cl1 Cl 0.48765(9) 0.42396(9) 0.2455(3) 0.1025(5) Uani 1 1 d . . . . .
C22 C 0.5003(9) 0.500000 0.343(2) 0.082(4) Uani 0.5 2 d S T P . .
H22A H 0.546289 0.499999 0.392155 0.098 Uiso 0.5 2 calc R U P . .
H22B H 0.472295 0.500000 0.432964 0.098 Uiso 0.5 2 calc R U P . .
C22B C 0.5278(7) 0.500000 0.216(2) 0.080(4) Uani 0.5 2 d S T P . .
H22C H 0.539796 0.500000 0.103987 0.096 Uiso 0.5 2 calc R U P . .
H22D H 0.569106 0.499999 0.287641 0.096 Uiso 0.5 2 calc R U P . .
Cl2 Cl 0.48386(15) 0.07350(16) 0.1849(6) 0.200(2) Uani 1 1 d . . . . .
C23 C 0.4883(7) 0.000000 0.299(2) 0.150(6) Uani 1 2 d S T P . .
H23A H 0.452062 0.000000 0.368631 0.180 Uiso 1 2 calc R U P . .
H23B H 0.530070 0.000001 0.369416 0.180 Uiso 1 2 calc R U P . .


_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 N1 2.254(5) 2_656 ?
I1 N1 2.254(5) . ?
N1 C2 1.340(7) . ?
N1 C3 1.354(7) . ?
N2 C5 1.325(8) . ?
N2 C6 1.507(12) . ?
N2 C10 1.528(13) . ?
C1 C2 1.339(8) . ?
C1 C5 1.418(8) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C4 1.333(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.417(7) . ?
C4 H4 0.9500 . ?
C6 C7 1.501(15) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.509(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.511(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.498(15) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.514(15) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.520(17) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.503(18) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
S1 O1 1.443(3) . ?
S1 O1 1.443(3) 6_565 ?
S1 N4 1.593(7) . ?
S1 C15 1.760(7) . ?
O2 C21 1.240(9) . ?
N4 C21 1.339(10) . ?
C15 C20 1.374(9) . ?
C15 C16 1.377(10) . ?
C16 C17 1.406(11) . ?
C16 H16 0.9500 . ?
C17 C18 1.379(12) . ?
C17 H17 0.9500 . ?
C18 C19 1.369(12) . ?
C18 H18 0.9500 . ?
C19 C20 1.391(10) . ?
C19 H19 0.9500 . ?
C20 C21 1.517(10) . ?
Cl1 C22 1.677(9) . ?
Cl1 C22B 1.702(8) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22B H22C 0.9900 . ?
C22B H22D 0.9900 . ?
Cl2 C23 1.697(10) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 I1 N1 177.4(2) 2_656 . ?
C2 N1 C3 117.0(5) . . ?
C2 N1 I1 123.9(4) . . ?
C3 N1 I1 119.1(4) . . ?
C5 N2 C6 125.2(8) . . ?
C5 N2 C10 123.5(8) . . ?
C6 N2 C10 106.5(10) . . ?
C2 C1 C5 120.5(5) . . ?
C2 C1 H1 119.8 . . ?
C5 C1 H1 119.8 . . ?
C1 C2 N1 123.6(5) . . ?
C1 C2 H2 118.2 . . ?
N1 C2 H2 118.2 . . ?
C4 C3 N1 123.3(5) . . ?
C4 C3 H3 118.3 . . ?
N1 C3 H3 118.3 . . ?
C3 C4 C5 120.7(5) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
N2 C5 C4 122.4(5) . . ?
N2 C5 C1 122.8(5) . . ?
C4 C5 C1 114.8(5) . . ?
C7 C6 N2 98.7(10) . . ?
C7 C6 H6A 112.0 . . ?
N2 C6 H6A 112.0 . . ?
C7 C6 H6B 112.0 . . ?
N2 C6 H6B 112.0 . . ?
H6A C6 H6B 109.7 . . ?
C6 C7 C8 108.4(14) . . ?
C6 C7 H7A 110.0 . . ?
C8 C7 H7A 110.0 . . ?
C6 C7 H7B 110.0 . . ?
C8 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
C7 C8 C9 113.5(15) . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 C8 106.1(14) . . ?
C10 C9 H9A 110.5 . . ?
C8 C9 H9A 110.5 . . ?
C10 C9 H9B 110.5 . . ?
C8 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
C9 C10 N2 102.0(12) . . ?
C9 C10 H10A 111.4 . . ?
N2 C10 H10A 111.4 . . ?
C9 C10 H10B 111.4 . . ?
N2 C10 H10B 111.4 . . ?
H10A C10 H10B 109.2 . . ?
C12 C11 H11A 111.3 . . ?
C12 C11 H11B 111.3 . . ?
H11A C11 H11B 109.2 . . ?
C11 C12 C13 103.2(12) . . ?
C11 C12 H12A 111.1 . . ?
C13 C12 H12A 111.1 . . ?
C11 C12 H12B 111.1 . . ?
C13 C12 H12B 111.1 . . ?
H12A C12 H12B 109.1 . . ?
C14 C13 C12 107.8(13) . . ?
C14 C13 H13A 110.2 . . ?
C12 C13 H13A 110.2 . . ?
C14 C13 H13B 110.2 . . ?
C12 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?
C13 C14 H14A 110.8 . . ?
C13 C14 H14B 110.8 . . ?
H14A C14 H14B 108.9 . . ?
O1 S1 O1 113.8(3) . 6_565 ?
O1 S1 N4 111.8(2) . . ?
O1 S1 N4 111.8(2) 6_565 . ?
O1 S1 C15 110.5(2) . . ?
O1 S1 C15 110.5(2) 6_565 . ?
N4 S1 C15 97.2(3) . . ?
C21 N4 S1 112.2(5) . . ?
C20 C15 C16 122.1(7) . . ?
C20 C15 S1 107.3(5) . . ?
C16 C15 S1 130.6(5) . . ?
C15 C16 C17 117.3(7) . . ?
C15 C16 H16 121.4 . . ?
C17 C16 H16 121.4 . . ?
C18 C17 C16 120.4(8) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 121.7(7) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C20 118.3(7) . . ?
C18 C19 H19 120.9 . . ?
C20 C19 H19 120.9 . . ?
C15 C20 C19 120.3(7) . . ?
C15 C20 C21 110.3(6) . . ?
C19 C20 C21 129.4(7) . . ?
O2 C21 N4 126.3(7) . . ?
O2 C21 C20 120.7(7) . . ?
N4 C21 C20 113.0(6) . . ?
Cl1 C22 Cl1 120.3(11) . 6_565 ?
Cl1 C22 H22A 107.3 . . ?
Cl1 C22 H22A 107.3 6_565 . ?
Cl1 C22 H22B 107.3 . . ?
Cl1 C22 H22B 107.3 6_565 . ?
H22A C22 H22B 106.9 . . ?
Cl1 C22B Cl1 117.3(9) . 6_565 ?
Cl1 C22B H22C 108.0 . . ?
Cl1 C22B H22C 108.0 6_565 . ?
Cl1 C22B H22D 108.0 . . ?
Cl1 C22B H22D 108.0 6_565 . ?
H22C C22B H22D 107.2 . . ?
Cl2 C23 Cl2 111.8(10) . 6 ?
Cl2 C23 H23A 109.3 . . ?
Cl2 C23 H23A 109.3 6 . ?
Cl2 C23 H23B 109.3 . . ?
Cl2 C23 H23B 109.3 6 . ?
H23A C23 H23B 107.9 . . ?

_refine_diff_density_max         0.866
_refine_diff_density_min         -1.090
_refine_diff_density_rms         0.082



####################################################################### 
# 
# 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_4cd
_database_code_depnum_ccdc_archive 'CCDC 2255954'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        OID-016-2
_chemical_name_common            
(NISac+4-Morpholinopyridine)+4-Piperidinopyridine
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H26 I N4 O, C7 H4 N O3 S'
_chemical_formula_sum            'C26 H30 I N5 O4 S'
_chemical_formula_weight         635.51

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.3752(7)
_cell_length_b                   10.3497(8)
_cell_length_c                   19.4856(14)
_cell_angle_alpha                101.771(3)
_cell_angle_beta                 92.584(2)
_cell_angle_gamma                113.863(3)
_cell_volume                     1496.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    3909
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      27.878

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_F_000             644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    1.177
_shelx_estimated_absorpt_T_min   0.853
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6389
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5383
_diffrn_reflns_av_unetI/netI     0.3411
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.664
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5383
_reflns_number_gt                1935
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Structure factors included contributions from the .fab file.
 
 _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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0541P)²] 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         5383
_refine_ls_number_parameters     323
_refine_ls_number_restraints     186
_refine_ls_R_factor_all          0.2542
_refine_ls_R_factor_gt           0.1047
_refine_ls_wR_factor_ref         0.2189
_refine_ls_wR_factor_gt          0.1778
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.002
_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 0.2463(2) 0.48937(15) 0.50090(8) 0.0387(4) Uani 1 1 d . . . . .
O1 O -0.3404(17) 0.2680(12) 0.0480(5) 0.045(4) Uani 1 1 d . . . . .
N1 N 0.387(2) 0.5462(17) 0.6133(8) 0.051(5) Uani 1 1 d . . . . .
N2 N 0.6584(19) 0.6496(15) 0.8154(7) 0.033(3) Uani 1 1 d . . . . .
N3 N 0.105(2) 0.4359(16) 0.3910(6) 0.037(4) Uani 1 1 d . . . . .
N4 N -0.162(2) 0.3346(15) 0.1886(7) 0.045(5) Uani 1 1 d . . . . .
C1 C 0.600(3) 0.7224(19) 0.7081(9) 0.045(5) Uani 1 1 d . . . . .
H1 H 0.685914 0.819881 0.726177 0.054 Uiso 1 1 calc R U . . .
C2 C 0.501(3) 0.683(2) 0.6408(10) 0.050(6) Uani 1 1 d . . . . .
H2 H 0.515873 0.754343 0.614988 0.060 Uiso 1 1 calc R U . . .
C3 C 0.362(3) 0.4409(19) 0.6456(9) 0.046(6) Uani 1 1 d . . . . .
H3 H 0.282229 0.343302 0.623590 0.055 Uiso 1 1 calc R U . . .
C4 C 0.455(3) 0.4752(18) 0.7121(9) 0.044(5) Uani 1 1 d . . . . .
H4 H 0.438062 0.397805 0.734226 0.053 Uiso 1 1 calc R U . . .
C5 C 0.574(3) 0.6182(19) 0.7497(8) 0.033(3) Uani 1 1 d . . . . .
C6 C 0.793(2) 0.7920(17) 0.8429(9) 0.039(4) Uani 1 1 d . . . . .
H6A H 0.763546 0.862817 0.824133 0.047 Uiso 1 1 calc R U . . .
H6B H 0.906226 0.796837 0.827779 0.047 Uiso 1 1 calc R U . . .
C7 C 0.811(3) 0.8300(18) 0.9213(9) 0.054(6) Uani 1 1 d D . . . .
H7A H 0.911246 0.926653 0.940081 0.065 Uiso 1 1 calc R U . . .
H7B H 0.702842 0.836679 0.936084 0.065 Uiso 1 1 calc R U . . .
C8 C 0.842(2) 0.7224(16) 0.9517(8) 0.038(4) Uani 1 1 d D . . . .
H8A H 0.950802 0.715793 0.937748 0.045 Uiso 1 1 calc R U . . .
H8B H 0.856447 0.752560 1.004065 0.045 Uiso 1 1 calc R U . . .
C9 C 0.693(2) 0.5821(17) 0.9266(8) 0.038(4) Uani 1 1 d D . . . .
H9A H 0.585649 0.587285 0.943499 0.045 Uiso 1 1 calc R U . . .
H9B H 0.714989 0.508312 0.945734 0.045 Uiso 1 1 calc R U . . .
C10 C 0.664(3) 0.5361(18) 0.8444(8) 0.043(5) Uani 1 1 d . . . . .
H10A H 0.761194 0.512310 0.827772 0.052 Uiso 1 1 calc R U . . .
H10B H 0.551985 0.447793 0.827619 0.052 Uiso 1 1 calc R U . . .
C11 C -0.084(3) 0.2599(18) 0.2906(8) 0.037(5) Uani 1 1 d . . . . .
H11 H -0.155012 0.160829 0.267353 0.045 Uiso 1 1 calc R U . . .
C12 C 0.009(3) 0.2945(19) 0.3539(9) 0.049(6) Uani 1 1 d . . . . .
H12 H 0.008136 0.218332 0.374240 0.059 Uiso 1 1 calc R U . . .
C13 C 0.108(3) 0.5391(19) 0.3580(10) 0.057(7) Uani 1 1 d . . . . .
H13 H 0.176940 0.637352 0.383020 0.069 Uiso 1 1 calc R U . . .
C14 C 0.023(3) 0.5178(18) 0.2923(9) 0.046(6) Uani 1 1 d . . . . .
H14 H 0.030157 0.595297 0.271648 0.055 Uiso 1 1 calc R U . . .
C15 C -0.077(3) 0.3709(19) 0.2586(8) 0.031(4) Uani 1 1 d . . . . .
C16 C -0.310(3) 0.1852(17) 0.1537(8) 0.050(5) Uani 1 1 d . . . . .
H16A H -0.424101 0.181356 0.166985 0.060 Uiso 1 1 calc R U . . .
H16B H -0.288105 0.108590 0.170134 0.060 Uiso 1 1 calc R U . . .
C17 C -0.317(3) 0.1583(18) 0.0725(8) 0.042(5) Uani 1 1 d . . . . .
H17A H -0.205545 0.154753 0.059302 0.051 Uiso 1 1 calc R U . . .
H17B H -0.415091 0.062969 0.049663 0.051 Uiso 1 1 calc R U . . .
C18 C -0.194(3) 0.3993(18) 0.0756(9) 0.052(5) Uani 1 1 d . . . . .
H18A H -0.201969 0.474293 0.052931 0.062 Uiso 1 1 calc R U . . .
H18B H -0.086088 0.387546 0.064125 0.062 Uiso 1 1 calc R U . . .
C19 C -0.180(3) 0.4498(17) 0.1533(8) 0.049(6) Uani 1 1 d . . . . .
H19A H -0.286507 0.463694 0.165355 0.058 Uiso 1 1 calc R U . . .
H19B H -0.075866 0.544189 0.170740 0.058 Uiso 1 1 calc R U . . .
S1 S -0.1931(9) -0.1779(6) 0.1422(3) 0.0650(18) Uani 1 1 d . . . . .
O2 O -0.189(2) -0.0642(14) 0.1095(8) 0.097(6) Uani 1 1 d . . . . .
O3 O -0.3247(19) -0.3254(14) 0.1074(7) 0.081(5) Uani 1 1 d . . . . .
O4 O -0.050(3) -0.083(2) 0.3352(8) 0.121(6) Uani 1 1 d D . . . .
N5 N -0.234(3) -0.1383(17) 0.2285(9) 0.078(4) Uani 1 1 d . . . . .
C20 C 0.021(3) -0.1703(18) 0.1534(9) 0.053(4) Uani 1 1 d . . . . .
C21 C 0.142(3) -0.189(2) 0.1072(9) 0.062(6) Uani 1 1 d . . . . .
H21 H 0.116291 -0.199752 0.057750 0.075 Uiso 1 1 calc R U . . .
C22 C 0.300(2) -0.1900(16) 0.1357(9) 0.029(4) Uani 1 1 d . . . . .
H22 H 0.372161 -0.219043 0.105918 0.035 Uiso 1 1 calc R U . . .
C23 C 0.344(2) -0.1487(16) 0.2064(8) 0.039(4) Uani 1 1 d D . . . .
H23 H 0.456834 -0.137571 0.224374 0.047 Uiso 1 1 calc R U . . .
C24 C 0.245(3) -0.122(2) 0.2540(10) 0.067(5) Uani 1 1 d D . . . .
H24 H 0.285415 -0.096813 0.303205 0.080 Uiso 1 1 calc R U . . .
C25 C 0.076(3) -0.130(2) 0.2297(10) 0.061(5) Uani 1 1 d D . . . .
C26 C -0.069(3) -0.109(2) 0.2690(9) 0.067(4) Uani 1 1 d 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 N3 2.247(12) . ?
I1 N1 2.283(15) . ?
O1 C17 1.398(16) . ?
O1 C18 1.390(19) . ?
N1 C3 1.318(19) . ?
N1 C2 1.32(2) . ?
N2 C5 1.344(17) . ?
N2 C6 1.42(2) . ?
N2 C10 1.419(17) . ?
N3 C13 1.347(19) . ?
N3 C12 1.37(2) . ?
N4 C15 1.413(17) . ?
N4 C16 1.53(2) . ?
N4 C19 1.545(17) . ?
C1 C2 1.41(2) . ?
C1 C5 1.43(2) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C4 1.381(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.42(2) . ?
C4 H4 0.9500 . ?
C6 C7 1.48(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.462(14) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.446(15) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.553(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.328(19) . ?
C11 C15 1.397(19) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.37(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.40(2) . ?
C14 H14 0.9500 . ?
C16 C17 1.54(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.48(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
S1 O2 1.438(12) . ?
S1 O3 1.468(13) . ?
S1 N5 1.732(18) . ?
S1 C20 1.77(2) . ?
O4 C26 1.251(15) . ?
N5 C26 1.45(2) . ?
C20 C21 1.42(2) . ?
C20 C25 1.46(2) . ?
C21 C22 1.42(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.34(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.333(15) . ?
C23 H23 0.9500 . ?
C24 C25 1.431(16) . ?
C24 H24 0.9500 . ?
C25 C26 1.528(16) . ?

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
N3 I1 N1 178.9(6) . . ?
C17 O1 C18 108.9(12) . . ?
C3 N1 C2 122.8(16) . . ?
C3 N1 I1 119.1(13) . . ?
C2 N1 I1 117.9(12) . . ?
C5 N2 C6 117.8(15) . . ?
C5 N2 C10 119.9(15) . . ?
C6 N2 C10 117.8(13) . . ?
C13 N3 C12 116.1(14) . . ?
C13 N3 I1 122.7(12) . . ?
C12 N3 I1 121.2(11) . . ?
C15 N4 C16 123.1(14) . . ?
C15 N4 C19 122.3(13) . . ?
C16 N4 C19 109.3(12) . . ?
C2 C1 C5 121.0(17) . . ?
C2 C1 H1 119.5 . . ?
C5 C1 H1 119.5 . . ?
N1 C2 C1 120.5(16) . . ?
N1 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
N1 C3 C4 118.7(17) . . ?
N1 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C3 C4 C5 124.6(16) . . ?
C3 C4 H4 117.7 . . ?
C5 C4 H4 117.7 . . ?
N2 C5 C4 123.5(16) . . ?
N2 C5 C1 124.3(17) . . ?
C4 C5 C1 112.1(15) . . ?
N2 C6 C7 109.9(16) . . ?
N2 C6 H6A 109.7 . . ?
C7 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C7 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C8 C7 C6 112.0(14) . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C7 109.4(14) . . ?
C9 C8 H8A 109.8 . . ?
C7 C8 H8A 109.8 . . ?
C9 C8 H8B 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
C8 C9 C10 110.3(15) . . ?
C8 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
N2 C10 C9 110.8(13) . . ?
N2 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C12 C11 C15 119.2(16) . . ?
C12 C11 H11 120.4 . . ?
C15 C11 H11 120.4 . . ?
C11 C12 N3 122.4(15) . . ?
C11 C12 H12 118.8 . . ?
N3 C12 H12 118.8 . . ?
N3 C13 C14 127.1(16) . . ?
N3 C13 H13 116.4 . . ?
C14 C13 H13 116.4 . . ?
C13 C14 C15 113.5(15) . . ?
C13 C14 H14 123.3 . . ?
C15 C14 H14 123.3 . . ?
C11 C15 C14 121.6(15) . . ?
C11 C15 N4 119.5(15) . . ?
C14 C15 N4 118.8(15) . . ?
N4 C16 C17 109.2(15) . . ?
N4 C16 H16A 109.8 . . ?
C17 C16 H16A 109.8 . . ?
N4 C16 H16B 109.8 . . ?
C17 C16 H16B 109.8 . . ?
H16A C16 H16B 108.3 . . ?
O1 C17 C16 111.2(13) . . ?
O1 C17 H17A 109.4 . . ?
C16 C17 H17A 109.4 . . ?
O1 C17 H17B 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
O1 C18 C19 112.4(17) . . ?
O1 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
O1 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.9 . . ?
C18 C19 N4 109.0(13) . . ?
C18 C19 H19A 109.9 . . ?
N4 C19 H19A 109.9 . . ?
C18 C19 H19B 109.9 . . ?
N4 C19 H19B 109.9 . . ?
H19A C19 H19B 108.3 . . ?
O2 S1 O3 115.9(9) . . ?
O2 S1 N5 108.9(9) . . ?
O3 S1 N5 107.5(9) . . ?
O2 S1 C20 109.2(9) . . ?
O3 S1 C20 111.7(8) . . ?
N5 S1 C20 102.9(10) . . ?
C26 N5 S1 102.1(15) . . ?
C21 C20 C25 119.1(17) . . ?
C21 C20 S1 135.3(14) . . ?
C25 C20 S1 105.5(14) . . ?
C20 C21 C22 119.3(16) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C23 C22 C21 117.5(18) . . ?
C23 C22 H22 121.2 . . ?
C21 C22 H22 121.2 . . ?
C24 C23 C22 126.8(19) . . ?
C24 C23 H23 116.6 . . ?
C22 C23 H23 116.6 . . ?
C23 C24 C25 119.0(19) . . ?
C23 C24 H24 120.5 . . ?
C25 C24 H24 120.5 . . ?
C20 C25 C26 110.3(16) . . ?
C20 C25 C24 117.3(18) . . ?
C26 C25 C24 132.3(19) . . ?
O4 C26 N5 121(2) . . ?
O4 C26 C25 119(2) . . ?
N5 C26 C25 118.9(16) . . ?

_refine_diff_density_max         1.460
_refine_diff_density_min         -0.782
_refine_diff_density_rms         0.178




####################################################################### 
# 
# 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_4c_2
_database_code_depnum_ccdc_archive 'CCDC 2255952'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        OID-019-4
_chemical_name_common            
(NISac+4-Piperidinopyridine)+4-Morpholinopyridine
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 N1 O3 S1, C18 H24 I N4 O2'
_chemical_formula_sum            'C25 H28 I N5 O5 S'
_chemical_formula_weight         637.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

_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, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   37.415(4)
_cell_length_b                   9.3673(9)
_cell_length_c                   4.1753(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.294(2)
_cell_angle_gamma                90
_cell_volume                     1463.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    806
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      27.878

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_F_000             644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    1.207
_shelx_estimated_absorpt_T_min   0.699
_shelx_estimated_absorpt_T_max   0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3614
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4337
_diffrn_reflns_av_unetI/netI     0.1965
_diffrn_reflns_av_R_equivalents  0.0960
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         2.178
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             1366
_reflns_number_gt                670
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0921P)²] 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         1366
_refine_ls_number_parameters     122
_refine_ls_number_restraints     63
_refine_ls_R_factor_all          0.1628
_refine_ls_R_factor_gt           0.0847
_refine_ls_wR_factor_ref         0.2297
_refine_ls_wR_factor_gt          0.2000
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.049
_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 0.000000 -0.500000 0.000000 0.0928(10) Uani 1 4 d S T P . .
O1 O 0.2251(3) -0.500000 0.955(2) 0.064(3) Uani 1 2 d S T P . .
N1 N 0.0550(3) -0.500000 0.232(4) 0.095(5) Uani 1 2 d S T P . .
N2 N 0.1553(3) -0.500000 0.685(2) 0.045(3) Uani 1 2 d S T P . .
C1 C 0.0716(3) -0.6240(17) 0.324(2) 0.083(4) Uani 1 1 d . . . . .
H1 H 0.059654 -0.711575 0.280377 0.100 Uiso 1 1 calc R U . . .
C2 C 0.1035(3) -0.6291(13) 0.470(2) 0.062(3) Uani 1 1 d . . . . .
H2 H 0.114323 -0.718519 0.519106 0.074 Uiso 1 1 calc R U . . .
C3 C 0.1215(4) -0.500000 0.553(3) 0.050(4) Uani 1 2 d S T P . .
C4 C 0.1712(2) -0.6304(11) 0.814(2) 0.049(2) Uani 1 1 d . . . . .
H4A H 0.162613 -0.713275 0.686689 0.059 Uiso 1 1 calc R U . . .
H4B H 0.163786 -0.643866 1.037612 0.059 Uiso 1 1 calc R U . . .
C5 C 0.2111(2) -0.6232(12) 0.804(2) 0.057(3) Uani 1 1 d . . . . .
H5A H 0.221292 -0.708898 0.910076 0.069 Uiso 1 1 calc R U . . .
H5B H 0.218475 -0.624253 0.577642 0.069 Uiso 1 1 calc R U . . .
S1 S 0.1784(3) -1.000000 0.218(2) 0.061(3) Uani 0.5 2 d DS T P . .
O2 O 0.1956(4) -0.8697(12) 0.325(3) 0.058(3) Uani 0.5 1 d D . P . .
O3 O 0.0825(6) -1.000000 0.040(5) 0.089(7) Uani 0.5 2 d DS T P . .
N3 N 0.1366(5) -1.000000 0.309(6) 0.077(8) Uani 0.5 2 d DS T P . .
C6 C 0.1736(6) -1.000000 -0.202(4) 0.050(5) Uani 0.5 2 d DS T P . .
C7 C 0.1967(7) -1.000000 -0.459(5) 0.058(7) Uani 0.5 2 d DS T P . .
H7 H 0.221721 -1.000000 -0.417361 0.070 Uiso 0.5 2 calc R U P . .
C8 C 0.1842(10) -1.000000 -0.775(8) 0.058(7) Uani 0.5 2 d DS T P . .
H8 H 0.200089 -1.000000 -0.949635 0.070 Uiso 0.5 2 calc R U P . .
C9 C 0.1473(8) -1.000000 -0.823(7) 0.054(6) Uani 0.5 2 d DS T P . .
H9 H 0.137766 -1.000000 -1.035473 0.065 Uiso 0.5 2 calc R U P . .
C10 C 0.1243(8) -1.000000 -0.571(5) 0.054(6) Uani 0.5 2 d DS T P . .
H10 H 0.099183 -1.000000 -0.611859 0.065 Uiso 0.5 2 calc R U P . .
C11 C 0.1371(6) -1.000000 -0.261(4) 0.050(5) Uani 0.5 2 d DS T P . .
C12 C 0.1154(7) -1.000000 0.041(5) 0.058(6) Uani 0.5 2 d DS T P . .


_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 N1 2.256(14) . ?
I1 N1 2.256(14) 5_545 ?
O1 C5 1.411(11) 6_545 ?
O1 C5 1.411(11) . ?
N1 C1 1.367(15) 6_545 ?
N1 C1 1.368(15) . ?
N2 C3 1.368(16) . ?
N2 C4 1.457(11) . ?
N2 C4 1.457(11) 6_545 ?
C1 C2 1.331(15) . ?
C1 H1 0.9500 . ?
C2 C3 1.421(12) . ?
C2 H2 0.9500 . ?
C4 C5 1.494(12) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
S1 O2 1.445(12) . ?
S1 O2 1.445(12) 6_535 ?
S1 N3 1.619(18) . ?
S1 C6 1.757(16) . ?
O3 C12 1.229(17) . ?
N3 C12 1.356(19) . ?
C6 C11 1.383(18) . ?
C6 C7 1.394(18) . ?
C7 C8 1.39(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.39(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.376(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.368(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.517(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 I1 N1 180.0 . 5_545 ?
C5 O1 C5 109.7(10) 6_545 . ?
C1 N1 C1 116.3(15) 6_545 . ?
C1 N1 I1 121.6(7) 6_545 . ?
C1 N1 I1 121.6(7) . . ?
C3 N2 C4 121.0(5) . . ?
C3 N2 C4 121.0(5) . 6_545 ?
C4 N2 C4 113.9(10) . 6_545 ?
C2 C1 N1 123.8(14) . . ?
C2 C1 H1 118.1 . . ?
N1 C1 H1 118.1 . . ?
C1 C2 C3 119.7(12) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
N2 C3 C2 121.6(7) . 6_545 ?
N2 C3 C2 121.6(7) . . ?
C2 C3 C2 116.5(13) 6_545 . ?
N2 C4 C5 110.6(8) . . ?
N2 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
O1 C5 C4 112.7(9) . . ?
O1 C5 H5A 109.0 . . ?
C4 C5 H5A 109.0 . . ?
O1 C5 H5B 109.0 . . ?
C4 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C8 S1 C9 179(10) 1_556 1_556 ?
C8 S1 O2 62(3) 1_556 . ?
C9 S1 O2 118.5(7) 1_556 . ?
C8 S1 O2 62(3) 1_556 6_535 ?
C9 S1 O2 118.5(7) 1_556 6_535 ?
O2 S1 O2 115.3(12) . 6_535 ?
C8 S1 C7 57(10) 1_556 1_556 ?
C9 S1 C7 124.2(16) 1_556 1_556 ?
O2 S1 C7 62.1(7) . 1_556 ?
O2 S1 C7 62.1(7) 6_535 1_556 ?
C8 S1 N3 159(10) 1_556 . ?
O2 S1 N3 110.7(8) . . ?
O2 S1 N3 110.7(8) 6_535 . ?
C7 S1 N3 102.3(14) 1_556 . ?
C8 S1 C6 102(10) 1_556 . ?
C9 S1 C6 77.1(16) 1_556 . ?
O2 S1 C6 110.0(7) . . ?
O2 S1 C6 110.0(7) 6_535 . ?
C7 S1 C6 158.7(15) 1_556 . ?
N3 S1 C6 99.0(12) . . ?
C8 S1 C10 149(10) 1_556 1_556 ?
O2 S1 C10 106.2(7) . 1_556 ?
O2 S1 C10 106.2(7) 6_535 1_556 ?
C7 S1 C10 92.5(11) 1_556 1_556 ?
C6 S1 C10 108.8(11) . 1_556 ?
C8 S1 H8 48(10) 1_556 1_556 ?
C9 S1 H8 131(2) 1_556 1_556 ?
O2 S1 H8 82.3(11) . 1_556 ?
O2 S1 H8 82.3(11) 6_535 1_556 ?
C7 S1 H8 104(2) 1_556 1_556 ?
N3 S1 H8 153(2) . 1_556 ?
C6 S1 H8 54.3(19) . 1_556 ?
C10 S1 H8 163(2) 1_556 1_556 ?
C8 S1 H9 152(10) 1_556 1_556 ?
O2 S1 H9 122.4(6) . 1_556 ?
O2 S1 H9 122.4(6) 6_535 1_556 ?
C7 S1 H9 151.1(14) 1_556 1_556 ?
N3 S1 H9 48.8(10) . 1_556 ?
C6 S1 H9 50.2(11) . 1_556 ?
C10 S1 H9 58.6(10) 1_556 1_556 ?
H8 S1 H9 104.5 1_556 1_556 ?
C8 O2 C7 57.5(10) 1_556 1_556 ?
S1 O2 C7 60.6(12) . 1_556 ?
C10 N3 C9 174(6) 1_556 1_556 ?
C10 N3 C12 102(3) 1_556 . ?
C9 N3 C12 71(4) 1_556 . ?
C10 N3 S1 147(4) 1_556 . ?
C12 N3 S1 110.9(19) . . ?
C9 N3 C11 144(4) 1_556 1_556 ?
C12 N3 C11 144.9(19) . 1_556 ?
S1 N3 C11 104.2(16) . 1_556 ?
C10 N3 C8 144(4) 1_556 1_556 ?
C12 N3 C8 113(2) . 1_556 ?
C11 N3 C8 101.8(16) 1_556 1_556 ?
C10 N3 H9 140(4) 1_556 1_556 ?
S1 N3 H9 73.3(14) . 1_556 ?
C11 N3 H9 178(2) 1_556 1_556 ?
C8 N3 H9 75.8(18) 1_556 1_556 ?
C11 C6 C7 119(2) . . ?
C11 C6 S1 104.9(14) . . ?
C7 C6 S1 136.0(19) . . ?
C11 C6 C8 111.7(19) . 1_556 ?
C7 C6 C8 129(2) . 1_556 ?
C11 C6 C9 67.6(15) . 1_556 ?
C7 C6 C9 173(2) . 1_556 ?
C11 C6 H8 143(2) . 1_556 ?
C7 C6 H8 98(2) . 1_556 ?
C9 C6 H8 75.4(16) 1_556 1_556 ?
C7 C6 H9 157(2) . 1_556 ?
S1 C6 H9 67.5(14) . 1_556 ?
C8 C6 H9 74.3(13) 1_556 1_556 ?
H8 C6 H9 105.5 1_556 1_556 ?
C8 C7 C6 122(3) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C9 116(4) . . ?
C7 C8 H8 121.8 . . ?
C9 C8 H8 121.8 . . ?
C10 C9 C8 122(3) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C11 C10 C9 121(3) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C6 119.6(19) . . ?
C10 C11 C12 127(2) . . ?
C6 C11 C12 113.3(18) . . ?
C6 C11 N3 99.7(14) . 1_554 ?
C12 C11 N3 147(2) . 1_554 ?
C10 C11 C9 171(2) . 1_556 ?
C6 C11 C9 69.0(14) . 1_556 ?
N3 C11 C9 168.8(17) 1_554 1_556 ?
C10 C11 H9 161(3) . 1_556 ?
C6 C11 H9 79(2) . 1_556 ?
N3 C11 H9 179(3) 1_554 1_556 ?
O3 C12 C9 155(2) . 1_556 ?
O3 C12 N3 125(2) . . ?
O3 C12 C11 123(2) . . ?
C9 C12 C11 82.0(19) 1_556 . ?
N3 C12 C11 112(2) . . ?
O3 C12 C10 100.5(19) . 1_556 ?
C9 C12 C10 54.0(13) 1_556 1_556 ?
C11 C12 C10 136(2) . 1_556 ?
O3 C12 H9 159(3) . 1_556 ?
N3 C12 H9 76(3) . 1_556 ?
C10 C12 H9 100(3) 1_556 1_556 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C1 C2 -6(2) 6_545 . . . ?
I1 N1 C1 C2 -177.9(8) . . . . ?
N1 C1 C2 C3 3.1(19) . . . . ?
C4 N2 C3 C2 170.5(9) . . . 6_545 ?
C4 N2 C3 C2 14.4(17) 6_545 . . 6_545 ?
C4 N2 C3 C2 -14.4(17) . . . . ?
C4 N2 C3 C2 -170.5(9) 6_545 . . . ?
C1 C2 C3 N2 -175.6(10) . . . . ?
C1 C2 C3 C2 -0.3(18) . . . 6_545 ?
C3 N2 C4 C5 154.2(10) . . . . ?
C4 N2 C4 C5 -48.1(13) 6_545 . . . ?
C5 O1 C5 C4 -59.4(13) 6_545 . . . ?
N2 C4 C5 O1 53.7(11) . . . . ?
C9 S1 O2 C8 -179(13) 1_556 . . 1_556 ?
O2 S1 O2 C8 32(12) 6_535 . . 1_556 ?
C7 S1 O2 C8 65(13) 1_556 . . 1_556 ?
N3 S1 O2 C8 159(13) . . . 1_556 ?
C6 S1 O2 C8 -93(13) . . . 1_556 ?
C10 S1 O2 C8 149(13) 1_556 . . 1_556 ?
C8 S1 O2 C7 -65(13) 1_556 . . 1_556 ?
C9 S1 O2 C7 115.9(18) 1_556 . . 1_556 ?
O2 S1 O2 C7 -33.2(15) 6_535 . . 1_556 ?
N3 S1 O2 C7 93.3(14) . . . 1_556 ?
C6 S1 O2 C7 -158.3(15) . . . 1_556 ?
C10 S1 O2 C7 84.1(11) 1_556 . . 1_556 ?
C8 S1 N3 C10 0.000(8) 1_556 . . 1_556 ?
C9 S1 N3 C10 180.000(4) 1_556 . . 1_556 ?
O2 S1 N3 C10 -64.5(8) . . . 1_556 ?
O2 S1 N3 C10 64.5(8) 6_535 . . 1_556 ?
C7 S1 N3 C10 0.000(4) 1_556 . . 1_556 ?
C6 S1 N3 C10 180.000(4) . . . 1_556 ?
C8 S1 N3 C9 180.000(9) 1_556 . . 1_556 ?
O2 S1 N3 C9 115.5(8) . . . 1_556 ?
O2 S1 N3 C9 -115.5(8) 6_535 . . 1_556 ?
C7 S1 N3 C9 180.000(3) 1_556 . . 1_556 ?
C6 S1 N3 C9 0.000(2) . . . 1_556 ?
C10 S1 N3 C9 180.000(5) 1_556 . . 1_556 ?
C8 S1 N3 C12 180.000(8) 1_556 . . . ?
C9 S1 N3 C12 0.000(3) 1_556 . . . ?
O2 S1 N3 C12 115.5(8) . . . . ?
O2 S1 N3 C12 -115.5(8) 6_535 . . . ?
C7 S1 N3 C12 180.000(2) 1_556 . . . ?
C6 S1 N3 C12 0.000(2) . . . . ?
C10 S1 N3 C12 180.000(5) 1_556 . . . ?
C8 S1 N3 C11 0.000(7) 1_556 . . 1_556 ?
C9 S1 N3 C11 180.000(3) 1_556 . . 1_556 ?
O2 S1 N3 C11 -64.5(8) . . . 1_556 ?
O2 S1 N3 C11 64.5(8) 6_535 . . 1_556 ?
C7 S1 N3 C11 0.000(1) 1_556 . . 1_556 ?
C6 S1 N3 C11 180.000(2) . . . 1_556 ?
C10 S1 N3 C11 0.000(5) 1_556 . . 1_556 ?
C9 S1 N3 C8 180.00(3) 1_556 . . 1_556 ?
O2 S1 N3 C8 -64.5(8) . . . 1_556 ?
O2 S1 N3 C8 64.5(8) 6_535 . . 1_556 ?
C7 S1 N3 C8 0.00(3) 1_556 . . 1_556 ?
C6 S1 N3 C8 180.00(3) . . . 1_556 ?
C10 S1 N3 C8 0.00(3) 1_556 . . 1_556 ?
C8 S1 C6 C11 180.000(3) 1_556 . . . ?
C9 S1 C6 C11 0.000(1) 1_556 . . . ?
O2 S1 C6 C11 -116.0(8) . . . . ?
O2 S1 C6 C11 116.0(8) 6_535 . . . ?
C7 S1 C6 C11 180.000(2) 1_556 . . . ?
N3 S1 C6 C11 0.000(1) . . . . ?
C10 S1 C6 C11 0.000(1) 1_556 . . . ?
C8 S1 C6 C7 0.000(4) 1_556 . . . ?
C9 S1 C6 C7 180.000(3) 1_556 . . . ?
O2 S1 C6 C7 64.0(8) . . . . ?
O2 S1 C6 C7 -64.0(8) 6_535 . . . ?
C7 S1 C6 C7 0.000(5) 1_556 . . . ?
N3 S1 C6 C7 180.000(3) . . . . ?
C10 S1 C6 C7 180.000(3) 1_556 . . . ?
C9 S1 C6 C8 180.000(9) 1_556 . . 1_556 ?
O2 S1 C6 C8 64.0(8) . . . 1_556 ?
O2 S1 C6 C8 -64.0(8) 6_535 . . 1_556 ?
C7 S1 C6 C8 0.000(7) 1_556 . . 1_556 ?
N3 S1 C6 C8 180.000(9) . . . 1_556 ?
C10 S1 C6 C8 180.000(11) 1_556 . . 1_556 ?
C8 S1 C6 C9 180.000(3) 1_556 . . 1_556 ?
O2 S1 C6 C9 -116.0(8) . . . 1_556 ?
O2 S1 C6 C9 116.0(8) 6_535 . . 1_556 ?
C7 S1 C6 C9 180.000(3) 1_556 . . 1_556 ?
N3 S1 C6 C9 0.000(1) . . . 1_556 ?
C10 S1 C6 C9 0.0 1_556 . . 1_556 ?
C11 C6 C7 C8 0.000(2) . . . . ?
S1 C6 C7 C8 180.000(5) . . . . ?
C8 C6 C7 C8 180.000(5) 1_556 . . . ?
C6 C7 C8 C9 0.000(7) . . . . ?
C7 C8 C9 C10 0.000(7) . . . . ?
C8 C9 C10 C11 0.000(4) . . . . ?
C9 C10 C11 C6 0.000(3) . . . . ?
C9 C10 C11 C12 180.000(4) . . . . ?
C9 C10 C11 N3 0.000(7) . . . 1_554 ?
C7 C6 C11 C10 0.000(1) . . . . ?
S1 C6 C11 C10 180.000(3) . . . . ?
C8 C6 C11 C10 180.000(3) 1_556 . . . ?
C9 C6 C11 C10 180.000(3) 1_556 . . . ?
C7 C6 C11 C12 180.000(1) . . . . ?
S1 C6 C11 C12 0.000(2) . . . . ?
C8 C6 C11 C12 0.000(2) 1_556 . . . ?
C9 C6 C11 C12 0.000(2) 1_556 . . . ?
C7 C6 C11 N3 0.000(1) . . . 1_554 ?
S1 C6 C11 N3 180.000(3) . . . 1_554 ?
C8 C6 C11 N3 180.000(3) 1_556 . . 1_554 ?
C9 C6 C11 N3 180.000(2) 1_556 . . 1_554 ?
C7 C6 C11 C9 180.000(1) . . . 1_556 ?
S1 C6 C11 C9 0.000(2) . . . 1_556 ?
C8 C6 C11 C9 0.000(2) 1_556 . . 1_556 ?
C10 N3 C12 O3 0.000(2) 1_556 . . . ?
C9 N3 C12 O3 180.000(2) 1_556 . . . ?
S1 N3 C12 O3 180.0 . . . . ?
C11 N3 C12 O3 0.000(5) 1_556 . . . ?
C8 N3 C12 O3 180.0 1_556 . . . ?
C10 N3 C12 C9 180.000(2) 1_556 . . 1_556 ?
S1 N3 C12 C9 0.000(3) . . . 1_556 ?
C11 N3 C12 C9 180.000(5) 1_556 . . 1_556 ?
C8 N3 C12 C9 0.000(3) 1_556 . . 1_556 ?
C10 N3 C12 C11 180.000(2) 1_556 . . . ?
C9 N3 C12 C11 0.000(2) 1_556 . . . ?
S1 N3 C12 C11 0.000(2) . . . . ?
C11 N3 C12 C11 180.000(6) 1_556 . . . ?
C8 N3 C12 C11 0.000(2) 1_556 . . . ?
C9 N3 C12 C10 180.000(2) 1_556 . . 1_556 ?
S1 N3 C12 C10 180.000(4) . . . 1_556 ?
C11 N3 C12 C10 0.000(7) 1_556 . . 1_556 ?
C8 N3 C12 C10 180.000(4) 1_556 . . 1_556 ?
C10 C11 C12 O3 0.000(2) . . . . ?
C6 C11 C12 O3 180.000(1) . . . . ?
N3 C11 C12 O3 0.000(4) 1_554 . . . ?
C9 C11 C12 O3 180.000(1) 1_556 . . . ?
C10 C11 C12 C9 180.000(2) . . . 1_556 ?
C6 C11 C12 C9 0.000(1) . . . 1_556 ?
N3 C11 C12 C9 180.000(4) 1_554 . . 1_556 ?
C10 C11 C12 N3 180.000(3) . . . . ?
C6 C11 C12 N3 0.000(1) . . . . ?
N3 C11 C12 N3 180.000(5) 1_554 . . . ?
C9 C11 C12 N3 0.000(3) 1_556 . . . ?
C10 C11 C12 C10 180.000(4) . . . 1_556 ?
C6 C11 C12 C10 0.000(2) . . . 1_556 ?
N3 C11 C12 C10 180.000(5) 1_554 . . 1_556 ?
C9 C11 C12 C10 0.000(3) 1_556 . . 1_556 ?

_refine_diff_density_max         0.704
_refine_diff_density_min         -1.163
_refine_diff_density_rms         0.152




####################################################################### 
# 
# 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_4c_1
_database_code_depnum_ccdc_archive 'CCDC 2255951'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        OID-015-4
_chemical_name_common            
(NISac+4-Morpholinopyridine)+4-Morpholinopyridine
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C18 H24 I N4 O2), 2(C7 H4 N O3 S), C3 H6 O'
_chemical_formula_sum            'C53 H62 I2 N10 O11 S2'
_chemical_formula_weight         1333.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.3294(5)
_cell_length_b                   10.2425(8)
_cell_length_c                   19.2668(15)
_cell_angle_alpha                76.797(2)
_cell_angle_beta                 88.922(3)
_cell_angle_gamma                66.018(4)
_cell_volume                     1457.06(19)
_cell_formula_units_Z            1
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    7711
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      28.700

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_F_000             676
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    1.217
_shelx_estimated_absorpt_T_min   0.727
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5726
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11171
_diffrn_reflns_av_unetI/netI     0.2351
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.243
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5250
_reflns_number_gt                2505
_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0941P)²] 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         5250
_refine_ls_number_parameters     349
_refine_ls_number_restraints     57
_refine_ls_R_factor_all          0.1820
_refine_ls_R_factor_gt           0.0933
_refine_ls_wR_factor_ref         0.2408
_refine_ls_wR_factor_gt          0.2073
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.037
_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 0.23406(11) 0.02865(10) 0.50100(5) 0.0364(4) Uani 1 1 d . . . . .
O1 O -0.1217(10) -0.2236(9) 0.9523(4) 0.033(2) Uani 1 1 d . . . . .
O2 O 0.6095(10) 0.2242(9) 0.0502(4) 0.035(2) Uani 1 1 d . . . . .
N1 N 0.1393(14) -0.0261(15) 0.6101(6) 0.044(3) Uani 1 1 d . . . . .
N2 N -0.0182(12) -0.1436(10) 0.8119(5) 0.024(2) Uani 1 1 d . . . . .
N3 N 0.3269(12) 0.0823(11) 0.3917(5) 0.029(3) Uani 1 1 d . . . . .
N4 N 0.5098(11) 0.1643(9) 0.1915(5) 0.022(2) Uani 1 1 d . . . . .
C1 C 0.1110(15) -0.2093(14) 0.7044(7) 0.032(3) Uani 1 1 d . . . . .
H1 H 0.131131 -0.309584 0.722310 0.039 Uiso 1 1 calc R U . . .
C2 C 0.1641(16) -0.1642(16) 0.6394(8) 0.037(3) Uani 1 1 d . . . . .
H2 H 0.222794 -0.236350 0.613371 0.044 Uiso 1 1 calc R U . . .
C3 C 0.0564(16) 0.0765(15) 0.6479(7) 0.038(3) Uani 1 1 d . . . . .
H3 H 0.040810 0.175177 0.628275 0.046 Uiso 1 1 calc R U . . .
C4 C -0.0035(15) 0.0448(13) 0.7108(7) 0.027(3) Uani 1 1 d . . . . .
H4 H -0.066267 0.121651 0.733667 0.033 Uiso 1 1 calc R U . . .
C5 C 0.0248(14) -0.1040(13) 0.7452(7) 0.027(3) Uani 1 1 d . . . . .
C6 C -0.0008(16) -0.2944(13) 0.8434(7) 0.032(3) Uani 1 1 d . . . . .
H6A H 0.103337 -0.365228 0.825970 0.039 Uiso 1 1 calc R U . . .
H6B H -0.106399 -0.304948 0.827680 0.039 Uiso 1 1 calc R U . . .
C7 C 0.0197(16) -0.3311(14) 0.9252(7) 0.034(3) Uani 1 1 d . . . . .
H7A H 0.020608 -0.429599 0.944660 0.041 Uiso 1 1 calc R U . . .
H7B H 0.133519 -0.333893 0.941273 0.041 Uiso 1 1 calc R U . . .
C8 C -0.1129(16) -0.0852(13) 0.9264(7) 0.032(3) Uani 1 1 d . . . . .
H8A H 0.004841 -0.093760 0.941187 0.039 Uiso 1 1 calc R U . . .
H8B H -0.201932 -0.011315 0.948423 0.039 Uiso 1 1 calc R U . . .
C9 C -0.1453(14) -0.0321(12) 0.8456(6) 0.024(3) Uani 1 1 d . . . . .
H9A H -0.267032 -0.014295 0.830684 0.029 Uiso 1 1 calc R U . . .
H9B H -0.132285 0.061828 0.829728 0.029 Uiso 1 1 calc R U . . .
C10 C 0.3527(15) 0.2516(13) 0.2914(7) 0.028(3) Uani 1 1 d . . . . .
H10 H 0.326488 0.351394 0.268495 0.034 Uiso 1 1 calc R U . . .
C11 C 0.2931(16) 0.2174(14) 0.3555(7) 0.032(3) Uani 1 1 d . . . . .
H11 H 0.221907 0.295994 0.375858 0.038 Uiso 1 1 calc R U . . .
C12 C 0.4288(15) -0.0306(13) 0.3634(7) 0.031(3) Uani 1 1 d . . . . .
H12 H 0.455343 -0.128590 0.389561 0.038 Uiso 1 1 calc R U . . .
C13 C 0.4951(15) -0.0084(12) 0.2984(6) 0.027(3) Uani 1 1 d . . . . .
H13 H 0.567598 -0.090638 0.280610 0.033 Uiso 1 1 calc R U . . .
C14 C 0.4568(14) 0.1350(12) 0.2578(6) 0.020(3) Uani 1 1 d . . . . .
C15 C 0.5034(15) 0.3099(12) 0.1574(6) 0.027(3) Uani 1 1 d . . . . .
H15A H 0.615077 0.314502 0.170420 0.032 Uiso 1 1 calc R U . . .
H15B H 0.405741 0.386265 0.174950 0.032 Uiso 1 1 calc R U . . .
C16 C 0.4759(17) 0.3398(13) 0.0771(6) 0.034(3) Uani 1 1 d . . . . .
H16A H 0.357895 0.346733 0.063921 0.041 Uiso 1 1 calc R U . . .
H16B H 0.480428 0.435239 0.054694 0.041 Uiso 1 1 calc R U . . .
C17 C 0.5939(15) 0.0898(13) 0.0795(6) 0.028(3) Uani 1 1 d . . . . .
H17A H 0.678317 0.011458 0.058560 0.034 Uiso 1 1 calc R U . . .
H17B H 0.473453 0.101382 0.066828 0.034 Uiso 1 1 calc R U . . .
C18 C 0.6299(14) 0.0444(11) 0.1597(6) 0.021(2) Uani 1 1 d . . . . .
H18A H 0.611542 -0.046376 0.178834 0.025 Uiso 1 1 calc R U . . .
H18B H 0.753979 0.023187 0.172635 0.025 Uiso 1 1 calc R U . . .
S1 S 0.0209(4) 0.6768(4) 0.1411(2) 0.0400(10) Uani 1 1 d . . . . .
O3 O 0.1305(11) 0.5644(9) 0.1064(5) 0.051(3) Uani 1 1 d . . . . .
O4 O 0.0005(12) 0.8238(9) 0.1062(5) 0.051(3) Uani 1 1 d . . . . .
O5 O -0.0282(14) 0.5818(11) 0.3329(6) 0.069(3) Uani 1 1 d . . . . .
N5 N 0.0841(13) 0.6344(11) 0.2253(6) 0.036(3) Uani 1 1 d . . . . .
C19 C -0.1885(16) 0.6730(12) 0.1503(7) 0.034(2) Uani 1 1 d . . . . .
C20 C -0.3228(15) 0.6974(12) 0.1010(8) 0.035(2) Uani 1 1 d . . . . .
H20 H -0.313928 0.719187 0.050776 0.042 Uiso 1 1 calc R U . . .
C21 C -0.4759(15) 0.6869(11) 0.1320(7) 0.0283(19) Uani 1 1 d . . . . .
H21 H -0.575139 0.708594 0.100749 0.034 Uiso 1 1 calc R U . . .
C22 C -0.4866(16) 0.6499(13) 0.1994(8) 0.037(2) Uani 1 1 d . . . . .
H22 H -0.589827 0.639346 0.215967 0.044 Uiso 1 1 calc R U . . .
C23 C -0.3591(16) 0.6258(14) 0.2465(8) 0.042(2) Uani 1 1 d . . . . .
H23 H -0.373307 0.601550 0.296116 0.050 Uiso 1 1 calc R U . . .
C24 C -0.2035(15) 0.6357(12) 0.2241(7) 0.0314(19) Uani 1 1 d . . . . .
C25 C -0.0412(16) 0.6173(14) 0.2660(8) 0.037(2) Uani 1 1 d . . . . .
O6 O -0.812(3) 0.530(3) 0.5019(14) 0.088(5) Uiso 0.5 1 d . U P . .
C26 C -0.675(5) 0.490(4) 0.469(2) 0.088(5) Uiso 0.5 1 d . U P . .
C27 C -0.637(5) 0.546(4) 0.395(2) 0.088(5) Uiso 0.5 1 d . U P . .
H27A H -0.729442 0.555292 0.360595 0.132 Uiso 0.5 1 calc R U P . .
H27B H -0.522552 0.476444 0.384368 0.132 Uiso 0.5 1 calc R U P . .
H27C H -0.634778 0.641996 0.390456 0.132 Uiso 0.5 1 calc R U P . .
C28 C -0.559(5) 0.354(4) 0.496(2) 0.088(5) Uiso 0.5 1 d . U P . .
H28A H -0.442023 0.354266 0.501957 0.132 Uiso 0.5 1 calc R U P . .
H28B H -0.554903 0.292128 0.463645 0.132 Uiso 0.5 1 calc R U P . .
H28C H -0.592574 0.316015 0.542584 0.132 Uiso 0.5 1 calc R U P . .


_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 N3 2.257(10) . ?
I1 N1 2.261(11) . ?
O1 C8 1.422(14) . ?
O1 C7 1.434(13) . ?
O2 C17 1.421(14) . ?
O2 C16 1.448(13) . ?
N1 C2 1.329(16) . ?
N1 C3 1.361(15) . ?
N2 C5 1.346(14) . ?
N2 C6 1.473(15) . ?
N2 C9 1.475(12) . ?
N3 C11 1.315(15) . ?
N3 C12 1.352(13) . ?
N4 C14 1.352(13) . ?
N4 C15 1.465(14) . ?
N4 C18 1.486(12) . ?
C1 C2 1.363(17) . ?
C1 C5 1.425(15) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C4 1.324(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.438(16) . ?
C4 H4 0.9500 . ?
C6 C7 1.530(16) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.518(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.347(16) . ?
C10 C14 1.445(14) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.367(15) . ?
C12 H12 0.9500 . ?
C13 C14 1.406(16) . ?
C13 H13 0.9500 . ?
C15 C16 1.511(16) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.505(15) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
S1 O4 1.443(10) . ?
S1 O3 1.443(8) . ?
S1 N5 1.619(11) . ?
S1 C19 1.765(12) . ?
O5 C25 1.251(16) . ?
N5 C25 1.337(15) . ?
C19 C20 1.387(16) . ?
C19 C24 1.402(17) . ?
C20 C21 1.431(16) . ?
C20 H20 0.9500 . ?
C21 C22 1.279(17) . ?
C21 H21 0.9500 . ?
C22 C23 1.317(17) . ?
C22 H22 0.9500 . ?
C23 C24 1.393(16) . ?
C23 H23 0.9500 . ?
C24 C25 1.509(17) . ?
O6 C26 1.26(4) . ?
C26 C28 1.31(5) . ?
C26 C27 1.49(5) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 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
N3 I1 N1 179.4(4) . . ?
C8 O1 C7 107.8(9) . . ?
C17 O2 C16 108.6(8) . . ?
C2 N1 C3 117.6(12) . . ?
C2 N1 I1 119.3(9) . . ?
C3 N1 I1 123.1(10) . . ?
C5 N2 C6 121.8(9) . . ?
C5 N2 C9 120.4(10) . . ?
C6 N2 C9 113.7(9) . . ?
C11 N3 C12 118.4(11) . . ?
C11 N3 I1 123.4(7) . . ?
C12 N3 I1 118.2(8) . . ?
C14 N4 C15 121.6(8) . . ?
C14 N4 C18 121.3(9) . . ?
C15 N4 C18 114.1(9) . . ?
C2 C1 C5 119.1(12) . . ?
C2 C1 H1 120.4 . . ?
C5 C1 H1 120.4 . . ?
N1 C2 C1 124.3(11) . . ?
N1 C2 H2 117.9 . . ?
C1 C2 H2 117.9 . . ?
C4 C3 N1 122.9(13) . . ?
C4 C3 H3 118.5 . . ?
N1 C3 H3 118.5 . . ?
C3 C4 C5 121.2(11) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
N2 C5 C1 121.9(12) . . ?
N2 C5 C4 123.2(9) . . ?
C1 C5 C4 114.8(11) . . ?
N2 C6 C7 111.6(9) . . ?
N2 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
O1 C7 C6 110.9(10) . . ?
O1 C7 H7A 109.5 . . ?
C6 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
O1 C8 C9 112.4(9) . . ?
O1 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
O1 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
N2 C9 C8 109.9(9) . . ?
N2 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
N2 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C11 C10 C14 119.3(11) . . ?
C11 C10 H10 120.4 . . ?
C14 C10 H10 120.4 . . ?
N3 C11 C10 124.4(11) . . ?
N3 C11 H11 117.8 . . ?
C10 C11 H11 117.8 . . ?
N3 C12 C13 122.1(11) . . ?
N3 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
C12 C13 C14 120.6(10) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
N4 C14 C13 123.3(9) . . ?
N4 C14 C10 121.5(10) . . ?
C13 C14 C10 115.2(10) . . ?
N4 C15 C16 110.3(9) . . ?
N4 C15 H15A 109.6 . . ?
C16 C15 H15A 109.6 . . ?
N4 C15 H15B 109.6 . . ?
C16 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
O2 C16 C15 111.1(10) . . ?
O2 C16 H16A 109.4 . . ?
C15 C16 H16A 109.4 . . ?
O2 C16 H16B 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
O2 C17 C18 111.6(9) . . ?
O2 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
O2 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
N4 C18 C17 109.7(9) . . ?
N4 C18 H18A 109.7 . . ?
C17 C18 H18A 109.7 . . ?
N4 C18 H18B 109.7 . . ?
C17 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
O4 S1 O3 114.5(6) . . ?
O4 S1 N5 111.9(5) . . ?
O3 S1 N5 111.4(6) . . ?
O4 S1 C19 109.7(6) . . ?
O3 S1 C19 110.2(5) . . ?
N5 S1 C19 98.0(6) . . ?
C25 N5 S1 111.0(9) . . ?
C20 C19 C24 121.3(11) . . ?
C20 C19 S1 132.7(11) . . ?
C24 C19 S1 106.0(9) . . ?
C19 C20 C21 114.4(12) . . ?
C19 C20 H20 122.8 . . ?
C21 C20 H20 122.8 . . ?
C22 C21 C20 123.7(13) . . ?
C22 C21 H21 118.2 . . ?
C20 C21 H21 118.2 . . ?
C21 C22 C23 122.1(13) . . ?
C21 C22 H22 118.9 . . ?
C23 C22 H22 118.9 . . ?
C22 C23 C24 120.6(14) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C23 C24 C19 117.9(12) . . ?
C23 C24 C25 131.3(13) . . ?
C19 C24 C25 110.8(11) . . ?
O5 C25 N5 125.3(13) . . ?
O5 C25 C24 120.5(12) . . ?
N5 C25 C24 114.1(12) . . ?
O6 C26 C28 114(4) . . ?
O6 C26 C27 132(4) . . ?
C28 C26 C27 111(3) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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
C3 N1 C2 C1 0.5(19) . . . . ?
I1 N1 C2 C1 -179.3(10) . . . . ?
C5 C1 C2 N1 -1(2) . . . . ?
C2 N1 C3 C4 -1.9(18) . . . . ?
I1 N1 C3 C4 178.0(10) . . . . ?
N1 C3 C4 C5 3.5(19) . . . . ?
C6 N2 C5 C1 -8.4(17) . . . . ?
C9 N2 C5 C1 -164.3(10) . . . . ?
C6 N2 C5 C4 175.0(10) . . . . ?
C9 N2 C5 C4 19.1(16) . . . . ?
C2 C1 C5 N2 -174.6(11) . . . . ?
C2 C1 C5 C4 2.3(17) . . . . ?
C3 C4 C5 N2 173.3(12) . . . . ?
C3 C4 C5 C1 -3.6(17) . . . . ?
C5 N2 C6 C7 155.8(10) . . . . ?
C9 N2 C6 C7 -46.9(13) . . . . ?
C8 O1 C7 C6 -62.3(12) . . . . ?
N2 C6 C7 O1 54.3(13) . . . . ?
C7 O1 C8 C9 64.5(12) . . . . ?
C5 N2 C9 C8 -155.2(10) . . . . ?
C6 N2 C9 C8 47.1(12) . . . . ?
O1 C8 C9 N2 -56.6(12) . . . . ?
C12 N3 C11 C10 0.4(18) . . . . ?
I1 N3 C11 C10 177.4(9) . . . . ?
C14 C10 C11 N3 1.9(19) . . . . ?
C11 N3 C12 C13 -0.9(17) . . . . ?
I1 N3 C12 C13 -178.1(9) . . . . ?
N3 C12 C13 C14 -0.8(19) . . . . ?
C15 N4 C14 C13 -165.8(10) . . . . ?
C18 N4 C14 C13 -6.6(16) . . . . ?
C15 N4 C14 C10 15.3(16) . . . . ?
C18 N4 C14 C10 174.5(9) . . . . ?
C12 C13 C14 N4 -176.0(11) . . . . ?
C12 C13 C14 C10 2.9(16) . . . . ?
C11 C10 C14 N4 175.6(11) . . . . ?
C11 C10 C14 C13 -3.4(16) . . . . ?
C14 N4 C15 C16 -150.6(10) . . . . ?
C18 N4 C15 C16 48.8(12) . . . . ?
C17 O2 C16 C15 62.6(12) . . . . ?
N4 C15 C16 O2 -55.1(13) . . . . ?
C16 O2 C17 C18 -63.4(11) . . . . ?
C14 N4 C18 C17 150.3(10) . . . . ?
C15 N4 C18 C17 -49.0(12) . . . . ?
O2 C17 C18 N4 56.2(11) . . . . ?
O4 S1 N5 C25 113.8(9) . . . . ?
O3 S1 N5 C25 -116.6(9) . . . . ?
C19 S1 N5 C25 -1.2(9) . . . . ?
O4 S1 C19 C20 63.8(12) . . . . ?
O3 S1 C19 C20 -63.1(13) . . . . ?
N5 S1 C19 C20 -179.5(11) . . . . ?
O4 S1 C19 C24 -116.9(8) . . . . ?
O3 S1 C19 C24 116.2(8) . . . . ?
N5 S1 C19 C24 -0.2(9) . . . . ?
C24 C19 C20 C21 2.4(15) . . . . ?
S1 C19 C20 C21 -178.3(9) . . . . ?
C19 C20 C21 C22 -3.9(16) . . . . ?
C20 C21 C22 C23 3.8(18) . . . . ?
C21 C22 C23 C24 -2.0(18) . . . . ?
C22 C23 C24 C19 0.5(17) . . . . ?
C22 C23 C24 C25 178.5(11) . . . . ?
C20 C19 C24 C23 -0.9(16) . . . . ?
S1 C19 C24 C23 179.7(8) . . . . ?
C20 C19 C24 C25 -179.2(9) . . . . ?
S1 C19 C24 C25 1.3(11) . . . . ?
S1 N5 C25 O5 178.6(10) . . . . ?
S1 N5 C25 C24 2.1(12) . . . . ?
C23 C24 C25 O5 3.0(19) . . . . ?
C19 C24 C25 O5 -179.0(11) . . . . ?
C23 C24 C25 N5 179.6(12) . . . . ?
C19 C24 C25 N5 -2.3(14) . . . . ?

_refine_diff_density_max         4.576
_refine_diff_density_min         -1.026
_refine_diff_density_rms         0.215



####################################################################### 
# 
# 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_4d
_database_code_depnum_ccdc_archive 'CCDC 2255955'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        OID-020-1
_chemical_name_common            
(NISac+4-Piperidinopyridine)+4-Piperidinopyridine)
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H28 I N4, C7 H4 N O3 S, 2(C H2 Cl2)'
_chemical_formula_sum            'C29 H36 Cl4 I N5 O3 S'
_chemical_formula_weight         803.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.7802(3)
_cell_length_b                   19.1082(7)
_cell_length_c                   20.1659(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.418(2)
_cell_angle_gamma                90
_cell_volume                     3373.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    6529
_cell_measurement_theta_min      2.6790
_cell_measurement_theta_max      27.4730

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_F_000             1624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    1.367
_shelx_estimated_absorpt_T_min   0.669
_shelx_estimated_absorpt_T_max   0.842
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.736
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.877
_oxdiff_exptl_absorpt_empirical_full_max 1.243
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18332
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.026
_diffrn_reflns_theta_max         26.249
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6800
_reflns_number_gt                5312
_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       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0439P)²+4.3519P] 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         6800
_refine_ls_number_parameters     398
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1147
_refine_ls_wR_factor_gt          0.1027
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.002
_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 0.50923(3) 0.22289(2) 0.51315(2) 0.02866(11) Uani 1 1 d . . . . .
N1 N 0.4250(4) 0.21964(16) 0.40545(17) 0.0257(8) Uani 1 1 d . . . . .
N2 N 0.2394(5) 0.21865(18) 0.2087(2) 0.0396(10) Uani 1 1 d . . . . .
N3 N 0.5933(4) 0.23092(17) 0.62101(18) 0.0277(8) Uani 1 1 d . . . . .
N4 N 0.7383(4) 0.25835(17) 0.82153(18) 0.0285(8) Uani 1 1 d . . . . .
C1 C 0.3454(4) 0.1566(2) 0.3065(2) 0.0265(9) Uani 1 1 d . . . . .
H1 H 0.333123 0.112656 0.284776 0.032 Uiso 1 1 calc R U . . .
C2 C 0.4040(4) 0.1596(2) 0.3708(2) 0.0275(9) Uani 1 1 d . . . . .
H2 H 0.431765 0.116846 0.392660 0.033 Uiso 1 1 calc R U . . .
C3 C 0.3897(5) 0.2797(2) 0.3725(2) 0.0280(9) Uani 1 1 d . . . . .
H3 H 0.406778 0.322704 0.395462 0.034 Uiso 1 1 calc R U . . .
C4 C 0.3310(5) 0.2819(2) 0.3082(2) 0.0264(9) Uani 1 1 d . . . . .
H4 H 0.308843 0.325777 0.287584 0.032 Uiso 1 1 calc R U . . .
C5 C 0.3023(5) 0.2192(2) 0.2714(2) 0.0257(9) Uani 1 1 d . . . . .
C6 C 0.2164(6) 0.1543(2) 0.1690(3) 0.0455(13) Uani 1 1 d . . . . .
H6A H 0.238775 0.113034 0.197713 0.055 Uiso 1 1 calc R U . . .
H6B H 0.287906 0.153905 0.133317 0.055 Uiso 1 1 calc R U . . .
C7 C 0.0544(5) 0.1501(3) 0.1384(2) 0.0421(12) Uani 1 1 d . . . . .
H7A H 0.042059 0.107388 0.110768 0.051 Uiso 1 1 calc R U . . .
H7B H -0.016534 0.146735 0.174190 0.051 Uiso 1 1 calc R U . . .
C8 C 0.0146(6) 0.2133(3) 0.0962(3) 0.0517(14) Uani 1 1 d . . . . .
H8A H -0.093887 0.210888 0.078875 0.062 Uiso 1 1 calc R U . . .
H8B H 0.078484 0.214382 0.057893 0.062 Uiso 1 1 calc R U . . .
C9 C 0.0416(5) 0.2796(3) 0.1377(3) 0.0465(13) Uani 1 1 d . . . . .
H9A H 0.022971 0.321199 0.108957 0.056 Uiso 1 1 calc R U . . .
H9B H -0.031266 0.281061 0.172805 0.056 Uiso 1 1 calc R U . . .
C10 C 0.2032(6) 0.2819(2) 0.1696(2) 0.0394(11) Uani 1 1 d . . . . .
H10A H 0.275552 0.286384 0.134485 0.047 Uiso 1 1 calc R U . . .
H10B H 0.215568 0.323459 0.198788 0.047 Uiso 1 1 calc R U . . .
C11 C 0.6672(5) 0.3066(2) 0.7121(2) 0.0279(9) Uani 1 1 d . . . . .
H11 H 0.683496 0.353105 0.727731 0.034 Uiso 1 1 calc R U . . .
C12 C 0.6193(5) 0.2953(2) 0.6479(2) 0.0293(10) Uani 1 1 d . . . . .
H12 H 0.602706 0.334915 0.619776 0.035 Uiso 1 1 calc R U . . .
C13 C 0.6154(5) 0.1754(2) 0.6623(2) 0.0268(9) Uani 1 1 d . . . . .
H13 H 0.596483 0.129820 0.644790 0.032 Uiso 1 1 calc R U . . .
C14 C 0.6638(4) 0.1822(2) 0.7281(2) 0.0247(9) Uani 1 1 d . . . . .
H14 H 0.677676 0.141518 0.755031 0.030 Uiso 1 1 calc R U . . .
C15 C 0.6936(4) 0.2492(2) 0.7567(2) 0.0243(9) Uani 1 1 d . . . . .
C16 C 0.7801(5) 0.3268(2) 0.8509(2) 0.0298(10) Uani 1 1 d . . . . .
H16A H 0.730730 0.332839 0.893016 0.036 Uiso 1 1 calc R U . . .
H16B H 0.743247 0.364580 0.820028 0.036 Uiso 1 1 calc R U . . .
C17 C 0.9528(5) 0.3320(2) 0.8642(2) 0.0364(11) Uani 1 1 d . . . . .
H17A H 1.002140 0.328884 0.821779 0.044 Uiso 1 1 calc R U . . .
H17B H 0.980339 0.377591 0.885167 0.044 Uiso 1 1 calc R U . . .
C18 C 1.0085(5) 0.2730(2) 0.9099(3) 0.0405(12) Uani 1 1 d . . . . .
H18A H 0.968573 0.279735 0.954037 0.049 Uiso 1 1 calc R U . . .
H18B H 1.121455 0.274214 0.915884 0.049 Uiso 1 1 calc R U . . .
C19 C 0.9575(5) 0.2020(2) 0.8823(2) 0.0362(11) Uani 1 1 d . . . . .
H19A H 0.987899 0.165037 0.915118 0.043 Uiso 1 1 calc R U . . .
H19B H 1.008155 0.192270 0.841122 0.043 Uiso 1 1 calc R U . . .
C20 C 0.7846(5) 0.2008(2) 0.8673(2) 0.0295(10) Uani 1 1 d . . . . .
H20A H 0.753103 0.155415 0.846817 0.035 Uiso 1 1 calc R U . . .
H20B H 0.733542 0.205945 0.909111 0.035 Uiso 1 1 calc R U . . .
S1 S 0.46709(12) 0.48825(5) 0.31207(6) 0.0278(2) Uani 1 1 d . . . . .
O1 O 0.5160(3) 0.42520(14) 0.34757(15) 0.0327(7) Uani 1 1 d . . . . .
O2 O 0.4861(4) 0.55122(14) 0.35118(16) 0.0387(8) Uani 1 1 d . . . . .
O3 O 0.4652(4) 0.49602(15) 0.13137(16) 0.0378(7) Uani 1 1 d . . . . .
N5 N 0.5432(4) 0.49431(16) 0.24271(18) 0.0311(9) Uani 1 1 d . . . . .
C21 C 0.2739(5) 0.4805(2) 0.2794(2) 0.0276(9) Uani 1 1 d . . . . .
C22 C 0.1411(5) 0.4745(2) 0.3114(2) 0.0360(10) Uani 1 1 d . . . . .
H22 H 0.142727 0.472624 0.358564 0.043 Uiso 1 1 calc R U . . .
C23 C 0.0047(5) 0.4712(2) 0.2714(3) 0.0424(12) Uani 1 1 d . . . . .
H23 H -0.089329 0.466892 0.291408 0.051 Uiso 1 1 calc R U . . .
C24 C 0.0049(5) 0.4741(2) 0.2027(3) 0.0421(12) Uani 1 1 d . . . . .
H24 H -0.089543 0.472104 0.176460 0.050 Uiso 1 1 calc R U . . .
C25 C 0.1395(5) 0.4800(2) 0.1715(2) 0.0341(10) Uani 1 1 d . . . . .
H25 H 0.138655 0.481347 0.124353 0.041 Uiso 1 1 calc R U . . .
C26 C 0.2755(5) 0.48380(19) 0.2112(2) 0.0272(9) Uani 1 1 d . . . . .
C27 C 0.4365(5) 0.49177(19) 0.1902(2) 0.0294(9) Uani 1 1 d . . . . .
Cl1 Cl 0.16052(16) 0.58555(8) -0.03011(8) 0.0618(4) Uani 1 1 d . . . . .
Cl2 Cl 0.2238(2) 0.43738(8) -0.01227(8) 0.0681(4) Uani 1 1 d . . . . .
C28 C 0.3016(7) 0.5216(3) -0.0144(3) 0.0606(11) Uani 1 1 d . . . . .
H28A H 0.374477 0.523747 -0.049400 0.073 Uiso 1 1 calc R U . . .
H28B H 0.358881 0.531654 0.028821 0.073 Uiso 1 1 calc R U . . .
Cl3 Cl 0.2542(13) 0.4223(3) 0.4936(6) 0.059(2) Uani 0.710(3) 1 d D . P A 1
Cl4 Cl 0.2424(3) 0.57527(11) 0.48956(12) 0.0733(7) Uani 0.710(3) 1 d D . P A 1
C29 C 0.2358(11) 0.5023(3) 0.5334(4) 0.0606(11) Uani 0.710(3) 1 d D . P A 1
H29A H 0.137171 0.501780 0.554110 0.073 Uiso 0.710(3) 1 calc R U P A 1
H29B H 0.317453 0.504962 0.569974 0.073 Uiso 0.710(3) 1 calc R U P A 1
Cl5 Cl 0.287(3) 0.4207(8) 0.4965(12) 0.049(3) Uani 0.290(3) 1 d D . P A 2
Cl6 Cl 0.1461(8) 0.5541(3) 0.5171(3) 0.0733(7) Uani 0.290(3) 1 d D . P A 2
C30 C 0.3340(19) 0.5088(8) 0.5034(11) 0.0606(11) Uani 0.290(3) 1 d D . P A 2
H30A H 0.376203 0.525985 0.462250 0.073 Uiso 0.290(3) 1 calc R U P A 2
H30B H 0.409944 0.516977 0.541440 0.073 Uiso 0.290(3) 1 calc R U P A 2


_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 N1 2.241(3) . ?
I1 N3 2.248(4) . ?
N1 C2 1.349(5) . ?
N1 C3 1.350(5) . ?
N2 C5 1.341(5) . ?
N2 C10 1.465(6) . ?
N2 C6 1.472(6) . ?
N3 C13 1.352(5) . ?
N3 C12 1.358(5) . ?
N4 C15 1.347(5) . ?
N4 C16 1.471(5) . ?
N4 C20 1.473(5) . ?
C1 C2 1.360(6) . ?
C1 C5 1.426(6) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C4 1.358(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.420(6) . ?
C4 H4 0.9500 . ?
C6 C7 1.509(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.503(7) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.527(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.512(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.346(6) . ?
C11 C15 1.427(6) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.369(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.420(6) . ?
C14 H14 0.9500 . ?
C16 C17 1.523(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.513(7) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.521(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.525(6) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
S1 O2 1.441(3) . ?
S1 O1 1.450(3) . ?
S1 N5 1.600(4) . ?
S1 C21 1.778(4) . ?
O3 C27 1.235(5) . ?
N5 C27 1.359(6) . ?
C21 C26 1.378(6) . ?
C21 C22 1.380(6) . ?
C22 C23 1.393(7) . ?
C22 H22 0.9500 . ?
C23 C24 1.386(7) . ?
C23 H23 0.9500 . ?
C24 C25 1.386(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.388(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.514(6) . ?
Cl1 C28 1.751(6) . ?
Cl2 C28 1.751(6) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
Cl3 C29 1.739(9) . ?
Cl4 C29 1.654(7) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
Cl5 C30 1.735(16) . ?
Cl6 C30 1.902(16) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 I1 N3 177.67(12) . . ?
C2 N1 C3 116.8(4) . . ?
C2 N1 I1 123.1(3) . . ?
C3 N1 I1 120.0(3) . . ?
C5 N2 C10 123.9(4) . . ?
C5 N2 C6 123.3(4) . . ?
C10 N2 C6 112.4(4) . . ?
C13 N3 C12 116.9(4) . . ?
C13 N3 I1 124.2(3) . . ?
C12 N3 I1 118.8(3) . . ?
C15 N4 C16 123.4(3) . . ?
C15 N4 C20 123.8(3) . . ?
C16 N4 C20 111.4(3) . . ?
C2 C1 C5 120.3(4) . . ?
C2 C1 H1 119.8 . . ?
C5 C1 H1 119.8 . . ?
N1 C2 C1 123.7(4) . . ?
N1 C2 H2 118.1 . . ?
C1 C2 H2 118.1 . . ?
N1 C3 C4 123.5(4) . . ?
N1 C3 H3 118.3 . . ?
C4 C3 H3 118.3 . . ?
C3 C4 C5 120.8(4) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
N2 C5 C4 122.9(4) . . ?
N2 C5 C1 122.3(4) . . ?
C4 C5 C1 114.8(4) . . ?
N2 C6 C7 110.6(4) . . ?
N2 C6 H6A 109.5 . . ?
C7 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C6 111.0(4) . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C7 C8 C9 109.7(4) . . ?
C7 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C10 C9 C8 111.0(4) . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
N2 C10 C9 111.2(4) . . ?
N2 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
N2 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C12 C11 C15 120.4(4) . . ?
C12 C11 H11 119.8 . . ?
C15 C11 H11 119.8 . . ?
C11 C12 N3 124.0(4) . . ?
C11 C12 H12 118.0 . . ?
N3 C12 H12 118.0 . . ?
N3 C13 C14 122.8(4) . . ?
N3 C13 H13 118.6 . . ?
C14 C13 H13 118.6 . . ?
C13 C14 C15 120.8(4) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
N4 C15 C14 122.8(4) . . ?
N4 C15 C11 122.2(4) . . ?
C14 C15 C11 114.9(4) . . ?
N4 C16 C17 110.0(3) . . ?
N4 C16 H16A 109.7 . . ?
C17 C16 H16A 109.7 . . ?
N4 C16 H16B 109.7 . . ?
C17 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C18 C17 C16 109.3(4) . . ?
C18 C17 H17A 109.8 . . ?
C16 C17 H17A 109.8 . . ?
C18 C17 H17B 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.3 . . ?
C17 C18 C19 111.7(4) . . ?
C17 C18 H18A 109.3 . . ?
C19 C18 H18A 109.3 . . ?
C17 C18 H18B 109.3 . . ?
C19 C18 H18B 109.3 . . ?
H18A C18 H18B 107.9 . . ?
C18 C19 C20 110.3(4) . . ?
C18 C19 H19A 109.6 . . ?
C20 C19 H19A 109.6 . . ?
C18 C19 H19B 109.6 . . ?
C20 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
N4 C20 C19 109.6(4) . . ?
N4 C20 H20A 109.8 . . ?
C19 C20 H20A 109.8 . . ?
N4 C20 H20B 109.8 . . ?
C19 C20 H20B 109.8 . . ?
H20A C20 H20B 108.2 . . ?
O2 S1 O1 113.97(19) . . ?
O2 S1 N5 112.31(19) . . ?
O1 S1 N5 111.34(18) . . ?
O2 S1 C21 109.80(19) . . ?
O1 S1 C21 110.61(18) . . ?
N5 S1 C21 97.6(2) . . ?
C27 N5 S1 111.6(3) . . ?
C26 C21 C22 123.0(4) . . ?
C26 C21 S1 106.4(3) . . ?
C22 C21 S1 130.5(3) . . ?
C21 C22 C23 116.9(4) . . ?
C21 C22 H22 121.6 . . ?
C23 C22 H22 121.6 . . ?
C24 C23 C22 120.6(5) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C25 C24 C23 121.6(4) . . ?
C25 C24 H24 119.2 . . ?
C23 C24 H24 119.2 . . ?
C24 C25 C26 117.9(4) . . ?
C24 C25 H25 121.1 . . ?
C26 C25 H25 121.1 . . ?
C21 C26 C25 119.9(4) . . ?
C21 C26 C27 111.4(4) . . ?
C25 C26 C27 128.6(4) . . ?
O3 C27 N5 124.5(4) . . ?
O3 C27 C26 122.6(4) . . ?
N5 C27 C26 112.9(4) . . ?
Cl2 C28 Cl1 112.0(3) . . ?
Cl2 C28 H28A 109.2 . . ?
Cl1 C28 H28A 109.2 . . ?
Cl2 C28 H28B 109.2 . . ?
Cl1 C28 H28B 109.2 . . ?
H28A C28 H28B 107.9 . . ?
Cl4 C29 Cl3 119.1(6) . . ?
Cl4 C29 H29A 107.5 . . ?
Cl3 C29 H29A 107.5 . . ?
Cl4 C29 H29B 107.5 . . ?
Cl3 C29 H29B 107.5 . . ?
H29A C29 H29B 107.0 . . ?
Cl5 C30 Cl6 104.6(11) . . ?
Cl5 C30 H30A 110.8 . . ?
Cl6 C30 H30A 110.8 . . ?
Cl5 C30 H30B 110.8 . . ?
Cl6 C30 H30B 110.8 . . ?
H30A C30 H30B 108.9 . . ?

_refine_diff_density_max         1.572
_refine_diff_density_min         -1.801
_refine_diff_density_rms         0.107



####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 2255956'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        'CS673E (MeOH)'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H10 I N'
_chemical_formula_sum            'C8 H10 I N'
_chemical_formula_weight         247.07

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'
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           45
_space_group_name_H-M_alt        'I b a 2'
_space_group_name_Hall           'I 2 -2c'

_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, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'x+1, -y+1, z+1/2'
'-x+1, y+1, z+1/2'

_cell_length_a                   22.1896(17)
_cell_length_b                   15.5327(11)
_cell_length_c                   4.9667(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1711.8(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2446
_cell_measurement_theta_min      2.5940
_cell_measurement_theta_max      24.8390

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.917
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    3.668
_shelx_estimated_absorpt_T_min   0.438
_shelx_estimated_absorpt_T_max   0.867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.65630
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.768
_oxdiff_exptl_absorpt_empirical_full_max 1.435
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11601
_diffrn_reflns_av_unetI/netI     0.0970
_diffrn_reflns_av_R_equivalents  0.1285
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         2.623
_diffrn_reflns_theta_max         25.241
_diffrn_reflns_theta_full        25.241
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1539
_reflns_number_gt                1084
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0467P)²] 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 362 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1539
_refine_ls_number_parameters     93
_refine_ls_number_restraints     40
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1237
_refine_ls_wR_factor_gt          0.1082
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.016
_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 0.39252(4) 0.59910(5) 0.7766(4) 0.0282(4) Uani 1 1 d . . . . .
N1 N 0.4590(5) 0.7304(8) 0.356(3) 0.027(3) Uani 1 1 d . . . . .
H1A H 0.472779 0.675437 0.419361 0.032 Uiso 1 1 calc R U . . .
H1B H 0.480995 0.760154 0.218020 0.032 Uiso 1 1 calc R U . . .
C1 C 0.4080(7) 0.7665(10) 0.463(4) 0.024(2) Uani 1 1 d . . . . .
C2 C 0.3756(7) 0.7273(11) 0.658(4) 0.029(2) Uani 1 1 d . . . . .
C3 C 0.3235(6) 0.7665(7) 0.765(7) 0.021(2) Uani 1 1 d . . . . .
H3 H 0.299045 0.735085 0.887503 0.025 Uiso 1 1 calc R U . . .
C4 C 0.3073(7) 0.8498(10) 0.696(3) 0.028(3) Uani 1 1 d . . . . .
C5 C 0.3423(7) 0.8923(10) 0.502(4) 0.024(4) Uani 1 1 d . . . . .
H5 H 0.331499 0.949018 0.448346 0.028 Uiso 1 1 calc R U . . .
C6 C 0.3925(7) 0.8531(11) 0.385(4) 0.029(3) Uani 1 1 d . . . . .
C7 C 0.2526(7) 0.8921(10) 0.813(9) 0.039(7) Uani 1 1 d . . . . .
H7A H 0.218623 0.851920 0.807321 0.059 Uiso 1 1 calc R U . . .
H7B H 0.242748 0.943596 0.707294 0.059 Uiso 1 1 calc R U . . .
H7C H 0.260700 0.908672 0.999627 0.059 Uiso 1 1 calc R U . . .
C8 C 0.4304(7) 0.8993(10) 0.179(3) 0.026(4) Uani 1 1 d . . . . .
H8A H 0.422822 0.874570 0.000731 0.039 Uiso 1 1 calc R U . . .
H8B H 0.473095 0.892816 0.224602 0.039 Uiso 1 1 calc R U . . .
H8C H 0.419770 0.960548 0.177750 0.039 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 C2 2.111(17) . ?
N1 C1 1.370(19) . ?
N1 H1A 0.9600 . ?
N1 H1B 0.9600 . ?
C1 C2 1.35(2) . ?
C1 C6 1.44(2) . ?
C2 C3 1.41(2) . ?
C3 C4 1.39(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.40(2) . ?
C4 C7 1.50(3) . ?
C5 C6 1.40(2) . ?
C5 H5 0.9500 . ?
C6 C8 1.51(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 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
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C2 C1 N1 122.2(15) . . ?
C2 C1 C6 119.1(16) . . ?
N1 C1 C6 118.4(15) . . ?
C1 C2 C3 120.8(18) . . ?
C1 C2 I1 122.1(13) . . ?
C3 C2 I1 116.5(13) . . ?
C4 C3 C2 122(2) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 117.7(17) . . ?
C3 C4 C7 121.7(19) . . ?
C5 C4 C7 120.5(17) . . ?
C6 C5 C4 121.4(15) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 119.1(16) . . ?
C5 C6 C8 121.3(15) . . ?
C1 C6 C8 119.6(15) . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_refine_diff_density_max         2.298
_refine_diff_density_min         -0.893
_refine_diff_density_rms         0.196



####################################################################### 
# 
# 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_4ac
_database_code_depnum_ccdc_archive 'CCDC 2255949'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        OID-013-4
_chemical_name_common            (NISac+4-Morpholinopyridine)+DMAP
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H22 I N4 O, C7 H4 N O3 S'
_chemical_formula_sum            'C23 H26 I N5 O4 S'
_chemical_formula_weight         595.45

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'
S S 0.3331 0.5567 '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      orthorhombic
_space_group_IT_number           64
_space_group_name_H-M_alt        'C m c a'
_space_group_name_Hall           '-C 2bc 2'

_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+1/2, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'x+1/2, -y, z-1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   18.6425(10)
_cell_length_b                   8.1736(3)
_cell_length_c                   35.9127(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5472.2(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3384
_cell_measurement_theta_min      4.7170
_cell_measurement_theta_max      75.1910

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_F_000             2400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    10.209
_shelx_estimated_absorpt_T_min   0.162
_shelx_estimated_absorpt_T_max   0.749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.66000
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.653
_oxdiff_exptl_absorpt_empirical_full_max 1.510
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20696
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_av_R_equivalents  0.0987
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.461
_diffrn_reflns_theta_max         69.994
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2684
_reflns_number_gt                1736
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0652P)²] 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         2684
_refine_ls_number_parameters     185
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1300
_refine_ls_wR_factor_gt          0.1142
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.026
_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 0.73233(3) 0.500000 0.500000 0.04182(17) Uani 1 2 d S T P . .
N1 N 0.7340(3) 0.6129(5) 0.55665(14) 0.0413(10) Uani 1 1 d . . . . .
N2 N 0.7420(3) 0.8371(7) 0.66083(17) 0.0539(14) Uani 0.5 1 d . . P . .
C1 C 0.6740(3) 0.7228(7) 0.60964(18) 0.0405(13) Uani 1 1 d . . . . .
H1 H 0.629834 0.744954 0.621799 0.049 Uiso 1 1 calc R U . . .
C2 C 0.6736(3) 0.6483(7) 0.57618(17) 0.0423(13) Uani 1 1 d . . . . .
H2 H 0.628569 0.619074 0.565689 0.051 Uiso 1 1 calc R U . . .
C3 C 0.7974(3) 0.6578(7) 0.57209(17) 0.0434(13) Uani 1 1 d . . . . .
H3 H 0.840333 0.637333 0.558644 0.052 Uiso 1 1 calc R U . . .
C4 C 0.8021(3) 0.7316(7) 0.6063(2) 0.0428(14) Uani 1 1 d . . . . .
H4 H 0.847824 0.758123 0.616300 0.051 Uiso 1 1 calc R U . . .
C5 C 0.7393(3) 0.7688(7) 0.62706(17) 0.0392(13) Uani 1 1 d . . . . .
C6 C 0.6773(3) 0.8974(7) 0.67917(18) 0.0461(14) Uani 0.5 1 d . . P . .
H6A H 0.655178 0.982757 0.663808 0.069 Uiso 0.5 1 calc R U P . .
H6B H 0.689829 0.942886 0.703555 0.069 Uiso 0.5 1 calc R U P . .
H6C H 0.643309 0.806976 0.682442 0.069 Uiso 0.5 1 calc R U P . .
C7 C 0.8099(3) 0.8879(8) 0.67776(19) 0.0496(15) Uani 0.5 1 d . . P . .
H7A H 0.835212 0.791554 0.687322 0.074 Uiso 0.5 1 calc R U P . .
H7B H 0.800324 0.963846 0.698281 0.074 Uiso 0.5 1 calc R U P . .
H7C H 0.839734 0.942346 0.658996 0.074 Uiso 0.5 1 calc R U P . .
O1A O 0.7454(5) 0.9628(10) 0.7366(2) 0.047(2) Uani 0.5 1 d . . P . .
N2A N 0.7420(3) 0.8371(7) 0.66083(17) 0.0539(14) Uani 0.5 1 d . . P . .
C6A C 0.6773(3) 0.8974(7) 0.67917(18) 0.0461(14) Uani 0.5 1 d D . P . .
H6A1 H 0.635637 0.832819 0.670377 0.055 Uiso 0.5 1 calc R U P . .
H6A2 H 0.669297 1.012665 0.671779 0.055 Uiso 0.5 1 calc R U P . .
C7A C 0.6809(6) 0.8871(15) 0.7233(3) 0.042(3) Uani 0.5 1 d D . P . .
H7A1 H 0.638774 0.943022 0.734254 0.050 Uiso 0.5 1 calc R U P . .
H7A2 H 0.679825 0.771149 0.731264 0.050 Uiso 0.5 1 calc R U P . .
C8A C 0.8057(6) 0.8768(16) 0.7224(3) 0.045(3) Uani 0.5 1 d D . P . .
H8A1 H 0.802579 0.760482 0.729906 0.054 Uiso 0.5 1 calc R U P . .
H8A2 H 0.850112 0.923017 0.733225 0.054 Uiso 0.5 1 calc R U P . .
C9A C 0.8099(3) 0.8879(8) 0.67776(19) 0.0496(15) Uani 0.5 1 d D . P . .
H9A1 H 0.820960 1.001783 0.670297 0.060 Uiso 0.5 1 calc R U P . .
H9A2 H 0.849111 0.816690 0.668615 0.060 Uiso 0.5 1 calc R U P . .
S1 S 0.500000 0.5740(3) 0.69032(8) 0.0478(5) Uani 1 2 d S T P . .
O2 O 0.5650(2) 0.6212(6) 0.70955(17) 0.0618(13) Uani 1 1 d . . . . .
O3 O 0.500000 0.5164(10) 0.5898(2) 0.074(2) Uani 1 2 d S T P . .
N3 N 0.500000 0.6343(10) 0.6475(3) 0.059(2) Uani 1 2 d S T P . .
C10 C 0.500000 0.3620(10) 0.6817(3) 0.050(2) Uani 1 2 d S T P . .
C11 C 0.500000 0.2312(11) 0.7062(4) 0.056(3) Uani 1 2 d S T P . .
H11 H 0.500000 0.246363 0.732419 0.067 Uiso 1 2 calc R U P . .
C12 C 0.500000 0.0757(12) 0.6901(4) 0.059(3) Uani 1 2 d S T P . .
H12 H 0.500000 -0.018231 0.705684 0.071 Uiso 1 2 calc R U P . .
C13 C 0.500000 0.0562(11) 0.6513(4) 0.061(3) Uani 1 2 d S T P . .
H13 H 0.500000 -0.051251 0.641229 0.073 Uiso 1 2 calc R U P . .
C14 C 0.500000 0.1892(13) 0.6270(3) 0.058(3) Uani 1 2 d S T P . .
H14 H 0.500000 0.174790 0.600747 0.069 Uiso 1 2 calc R U P . .
C15 C 0.500000 0.3431(10) 0.6430(3) 0.045(2) Uani 1 2 d S T P . .
C16 C 0.500000 0.5063(13) 0.6234(3) 0.056(2) Uani 1 2 d S T P . .


_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 N1 2.234(5) . ?
I1 N1 2.234(5) 4_566 ?
N1 C3 1.356(8) . ?
N1 C2 1.358(8) . ?
N2 C5 1.336(8) . ?
N2 C6 1.460(8) . ?
N2 C7 1.465(8) . ?
C1 C2 1.347(9) . ?
C1 C5 1.419(8) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C4 1.373(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.419(9) . ?
C4 H4 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
O1A O1A 0.979(17) 7_646 ?
O1A C8A 1.421(15) . ?
O1A C7A 1.433(14) . ?
O1A C8A 1.892(14) 7_646 ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?
C8A H8A1 0.9900 . ?
C8A H8A2 0.9900 . ?
S1 O2 1.448(5) 12_655 ?
S1 O2 1.448(5) . ?
S1 N3 1.614(10) . ?
S1 C10 1.760(9) . ?
O3 C16 1.210(13) . ?
N3 C16 1.357(14) . ?
C10 C11 1.383(14) . ?
C10 C15 1.399(15) . ?
C11 C12 1.396(15) . ?
C11 H11 0.9500 . ?
C12 C13 1.404(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.393(16) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(13) . ?
C14 H14 0.9500 . ?
C15 C16 1.508(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 I1 N1 178.4(3) . 4_566 ?
C3 N1 C2 117.0(5) . . ?
C3 N1 I1 119.7(4) . . ?
C2 N1 I1 123.2(4) . . ?
C5 N2 C6 121.3(5) . . ?
C5 N2 C7 121.8(6) . . ?
C6 N2 C7 115.6(5) . . ?
C2 C1 C5 121.2(6) . . ?
C2 C1 H1 119.4 . . ?
C5 C1 H1 119.4 . . ?
C1 C2 N1 123.5(6) . . ?
C1 C2 H2 118.3 . . ?
N1 C2 H2 118.3 . . ?
N1 C3 C4 122.7(6) . . ?
N1 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
C3 C4 C5 120.7(6) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
N2 C5 C1 122.9(6) . . ?
N2 C5 C4 122.3(6) . . ?
C1 C5 C4 114.8(6) . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1A O1A C8A 102.5(11) 7_646 . ?
O1A O1A C7A 118.2(12) 7_646 . ?
C8A O1A C7A 109.3(8) . . ?
O1A O1A C8A 47.1(8) 7_646 7_646 ?
C8A O1A C8A 119.7(10) . 7_646 ?
C7A O1A C8A 71.0(7) . 7_646 ?
O1A C7A H7A1 109.6 . . ?
O1A C7A H7A2 109.6 . . ?
H7A1 C7A H7A2 108.1 . . ?
O1A C8A H8A1 109.3 . . ?
O1A C8A H8A2 109.3 . . ?
H8A1 C8A H8A2 108.0 . . ?
O2 S1 O2 113.7(5) 12_655 . ?
O2 S1 N3 111.9(3) 12_655 . ?
O2 S1 N3 111.9(3) . . ?
O2 S1 C10 110.3(3) 12_655 . ?
O2 S1 C10 110.3(3) . . ?
N3 S1 C10 97.7(5) . . ?
C16 N3 S1 111.8(7) . . ?
C11 C10 C15 123.1(9) . . ?
C11 C10 S1 130.5(10) . . ?
C15 C10 S1 106.4(7) . . ?
C10 C11 C12 116.2(12) . . ?
C10 C11 H11 121.9 . . ?
C12 C11 H11 121.9 . . ?
C11 C12 C13 120.9(9) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 122.2(9) . . ?
C14 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
C15 C14 C13 116.7(11) . . ?
C15 C14 H14 121.7 . . ?
C13 C14 H14 121.7 . . ?
C14 C15 C10 120.9(9) . . ?
C14 C15 C16 127.6(10) . . ?
C10 C15 C16 111.5(8) . . ?
O3 C16 N3 125.7(10) . . ?
O3 C16 C15 121.7(10) . . ?
N3 C16 C15 112.6(9) . . ?

_refine_diff_density_max         1.906
_refine_diff_density_min         -0.836
_refine_diff_density_rms         0.096




####################################################################### 
# 
# 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_MPYH_NSac_1
_database_code_depnum_ccdc_archive 'CCDC 2255957'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        OID-039-4a
_chemical_name_common            
(NISac+4-Piperidinopyridine)+4-Morpholinopyridine
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H13 N2 O, C7 H4 N O3 S'
_chemical_formula_sum            'C16 H17 N3 O4 S'
_chemical_formula_weight         347.38

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'

_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                   13.5609(16)
_cell_length_b                   8.0439(9)
_cell_length_c                   14.5581(18)
_cell_angle_alpha                90
_cell_angle_beta                 98.598(2)
_cell_angle_gamma                90
_cell_volume                     1570.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1869
_cell_measurement_theta_min      2.2210
_cell_measurement_theta_max      28.0520

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.35
_exptl_absorpt_coefficient_mu    0.233
_shelx_estimated_absorpt_T_min   0.917
_shelx_estimated_absorpt_T_max   0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84594
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.920
_oxdiff_exptl_absorpt_empirical_full_max 1.177
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7130
_diffrn_reflns_av_unetI/netI     0.0631
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.915
_diffrn_reflns_theta_max         26.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3114
_reflns_number_gt                2174
_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       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0307P)²+4.2734P] 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         3114
_refine_ls_number_parameters     263
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.1111
_refine_ls_R_factor_gt           0.0762
_refine_ls_wR_factor_ref         0.1669
_refine_ls_wR_factor_gt          0.1457
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.040
_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
N1 N 0.6128(3) 0.2535(6) 0.4967(2) 0.0574(12) Uani 1 1 d . . . . .
H1N H 0.591148 0.159154 0.470540 0.069 Uiso 1 1 calc R U . . .
C1 C 0.5959(3) 0.4684(7) 0.6038(3) 0.0540(12) Uani 1 1 d . . . . .
H1 H 0.560613 0.514024 0.649507 0.065 Uiso 1 1 calc R U . . .
C2 C 0.5652(3) 0.3241(8) 0.5624(3) 0.0576(13) Uani 1 1 d . . . . .
H2 H 0.508494 0.269993 0.579748 0.069 Uiso 1 1 calc R U . . .
C3 C 0.6933(3) 0.3288(8) 0.4719(3) 0.0543(14) Uani 1 1 d . . . . .
H3 H 0.726242 0.278501 0.425878 0.065 Uiso 1 1 calc R U . . .
C4 C 0.7287(3) 0.4736(7) 0.5103(3) 0.0519(14) Uani 1 1 d . . . . .
H4 H 0.786029 0.522627 0.491075 0.062 Uiso 1 1 calc R U . . .
C5 C 0.6813(3) 0.5546(7) 0.5797(3) 0.0477(10) Uani 1 1 d . . . . .
O1 O 0.7571(8) 1.022(2) 0.6672(9) 0.042(2) Uani 0.525(10) 1 d D . P A 1
N2 N 0.7132(3) 0.6994(6) 0.6178(3) 0.0606(11) Uani 0.525(10) 1 d D . P A 1
C6 C 0.6323(6) 0.7961(12) 0.6451(7) 0.046(2) Uani 0.525(10) 1 d D . P A 1
H6A H 0.586752 0.726338 0.675956 0.055 Uiso 0.525(10) 1 calc R U P A 1
H6B H 0.593624 0.854167 0.591478 0.055 Uiso 0.525(10) 1 calc R U P A 1
C7 C 0.6904(7) 0.9176(17) 0.7127(7) 0.043(2) Uani 0.525(10) 1 d D . P A 1
H7A H 0.642991 0.989323 0.739998 0.051 Uiso 0.525(10) 1 calc R U P A 1
H7B H 0.730067 0.854785 0.763842 0.051 Uiso 0.525(10) 1 calc R U P A 1
C8 C 0.8305(7) 0.9063(15) 0.6387(7) 0.041(2) Uani 0.525(10) 1 d D . P A 1
H8A H 0.863584 0.845453 0.693996 0.050 Uiso 0.525(10) 1 calc R U P A 1
H8B H 0.882231 0.970227 0.612693 0.050 Uiso 0.525(10) 1 calc R U P A 1
C9 C 0.7836(6) 0.7829(11) 0.5673(6) 0.034(2) Uani 0.525(10) 1 d D . P A 1
H9A H 0.749258 0.839314 0.511066 0.041 Uiso 0.525(10) 1 calc R U P A 1
H9B H 0.833657 0.704385 0.549439 0.041 Uiso 0.525(10) 1 calc R U P A 1
O1B O 0.7613(13) 1.055(3) 0.6651(15) 0.085(7) Uani 0.475(10) 1 d D . P A 2
N2B N 0.7132(3) 0.6994(6) 0.6178(3) 0.0606(11) Uani 0.475(10) 1 d D . P A 2
C6B C 0.6752(8) 0.8009(13) 0.6996(8) 0.040(3) Uani 0.475(10) 1 d D . P A 2
H6B1 H 0.609659 0.757022 0.710408 0.048 Uiso 0.475(10) 1 calc R U P A 2
H6B2 H 0.722858 0.786734 0.757540 0.048 Uiso 0.475(10) 1 calc R U P A 2
C7B C 0.6654(8) 0.9835(14) 0.6752(9) 0.048(3) Uani 0.475(10) 1 d D . P A 2
H7B1 H 0.618979 0.997080 0.616433 0.057 Uiso 0.475(10) 1 calc R U P A 2
H7B2 H 0.637081 1.043380 0.724665 0.057 Uiso 0.475(10) 1 calc R U P A 2
C8B C 0.8068(10) 0.9675(16) 0.5954(9) 0.058(4) Uani 0.475(10) 1 d D . P A 2
H8B1 H 0.872983 1.016456 0.591251 0.070 Uiso 0.475(10) 1 calc R U P A 2
H8B2 H 0.764734 0.979756 0.534095 0.070 Uiso 0.475(10) 1 calc R U P A 2
C9B C 0.8186(7) 0.7860(15) 0.6197(10) 0.044(3) Uani 0.475(10) 1 d D . P A 2
H9B1 H 0.857823 0.774198 0.682397 0.053 Uiso 0.475(10) 1 calc R U P A 2
H9B2 H 0.855601 0.729996 0.574792 0.053 Uiso 0.475(10) 1 calc R U P A 2
S1 S 0.54848(7) 0.07612(16) 0.15890(7) 0.0413(3) Uani 1 1 d . . . . .
O2 O 0.4452(2) 0.1012(4) 0.12162(18) 0.0491(9) Uani 1 1 d . . . . .
O3 O 0.6195(2) 0.1644(4) 0.11178(18) 0.0442(8) Uani 1 1 d . . . . .
O4 O 0.6016(2) -0.0393(5) 0.40496(18) 0.0557(10) Uani 1 1 d . . . . .
N3 N 0.5680(2) 0.1133(5) 0.2701(2) 0.0463(9) Uani 1 1 d . . . . .
C11 C 0.5765(3) -0.1393(6) 0.1650(3) 0.0377(10) Uani 1 1 d . . . . .
C12 C 0.5760(3) -0.2572(6) 0.0961(3) 0.0434(11) Uani 1 1 d . . . . .
H12 H 0.559103 -0.228510 0.032374 0.052 Uiso 1 1 calc R U . . .
C13 C 0.6015(3) -0.4213(6) 0.1234(3) 0.0468(12) Uani 1 1 d . . . . .
H13 H 0.600658 -0.506333 0.077986 0.056 Uiso 1 1 calc R U . . .
C14 C 0.6281(3) -0.4590(7) 0.2180(3) 0.0512(13) Uani 1 1 d . . . . .
H14 H 0.647482 -0.569085 0.236175 0.061 Uiso 1 1 calc R U . . .
C15 C 0.6264(3) -0.3382(7) 0.2850(3) 0.0524(13) Uani 1 1 d . . . . .
H15 H 0.642950 -0.365609 0.348927 0.063 Uiso 1 1 calc R U . . .
C16 C 0.6004(3) -0.1769(6) 0.2586(3) 0.0430(10) Uani 1 1 d . . . . .
C17 C 0.5902(3) -0.0292(7) 0.3173(3) 0.0442(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C3 1.344(6) . ?
N1 C2 1.355(6) . ?
N1 H1N 0.8800 . ?
C1 C2 1.344(7) . ?
C1 C5 1.437(6) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C4 1.349(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.433(6) . ?
C4 H4 0.9500 . ?
C5 N2B 1.334(7) . ?
C5 N2 1.334(7) . ?
O1 C7 1.463(14) . ?
O1 C8 1.467(13) . ?
N2 C6 1.449(8) . ?
N2 C9 1.453(8) . ?
C6 C7 1.520(12) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.507(12) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
O1B C8B 1.447(15) . ?
O1B C7B 1.450(15) . ?
N2B C9B 1.586(10) . ?
N2B C6B 1.593(10) . ?
C6B C7B 1.512(14) . ?
C6B H6B1 0.9900 . ?
C6B H6B2 0.9900 . ?
C7B H7B1 0.9900 . ?
C7B H7B2 0.9900 . ?
C8B C9B 1.505(14) . ?
C8B H8B1 0.9900 . ?
C8B H8B2 0.9900 . ?
C9B H9B1 0.9900 . ?
C9B H9B2 0.9900 . ?
S1 O2 1.438(3) . ?
S1 O3 1.449(3) . ?
S1 N3 1.628(3) . ?
S1 C11 1.773(5) . ?
O4 C17 1.265(5) . ?
N3 C17 1.347(6) . ?
C11 C12 1.380(6) . ?
C11 C16 1.387(5) . ?
C12 C13 1.407(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.404(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.379(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.482(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
C3 N1 C2 119.5(5) . . ?
C3 N1 H1N 120.3 . . ?
C2 N1 H1N 120.3 . . ?
C2 C1 C5 120.9(4) . . ?
C2 C1 H1 119.5 . . ?
C5 C1 H1 119.5 . . ?
C1 C2 N1 121.9(4) . . ?
C1 C2 H2 119.0 . . ?
N1 C2 H2 119.0 . . ?
N1 C3 C4 122.1(4) . . ?
N1 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C5 121.0(4) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
N2B C5 C4 122.5(4) . . ?
N2 C5 C4 122.5(4) . . ?
N2B C5 C1 122.9(4) . . ?
N2 C5 C1 122.9(4) . . ?
C4 C5 C1 114.6(5) . . ?
C7 O1 C8 104.8(12) . . ?
C5 N2 C6 111.8(5) . . ?
C5 N2 C9 113.0(5) . . ?
C6 N2 C9 118.2(6) . . ?
N2 C6 C7 100.5(7) . . ?
N2 C6 H6A 111.7 . . ?
C7 C6 H6A 111.7 . . ?
N2 C6 H6B 111.7 . . ?
C7 C6 H6B 111.7 . . ?
H6A C6 H6B 109.4 . . ?
O1 C7 C6 111.9(9) . . ?
O1 C7 H7A 109.2 . . ?
C6 C7 H7A 109.2 . . ?
O1 C7 H7B 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
O1 C8 C9 112.3(9) . . ?
O1 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
O1 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
N2 C9 C8 101.4(7) . . ?
N2 C9 H9A 111.5 . . ?
C8 C9 H9A 111.5 . . ?
N2 C9 H9B 111.5 . . ?
C8 C9 H9B 111.5 . . ?
H9A C9 H9B 109.3 . . ?
C8B O1B C7B 111.1(15) . . ?
C5 N2B C9B 128.8(6) . . ?
C5 N2B C6B 129.6(5) . . ?
C9B N2B C6B 98.8(7) . . ?
C7B C6B N2B 110.4(7) . . ?
C7B C6B H6B1 109.6 . . ?
N2B C6B H6B1 109.6 . . ?
C7B C6B H6B2 109.6 . . ?
N2B C6B H6B2 109.6 . . ?
H6B1 C6B H6B2 108.1 . . ?
O1B C7B C6B 111.3(13) . . ?
O1B C7B H7B1 109.4 . . ?
C6B C7B H7B1 109.4 . . ?
O1B C7B H7B2 109.4 . . ?
C6B C7B H7B2 109.4 . . ?
H7B1 C7B H7B2 108.0 . . ?
O1B C8B C9B 110.5(14) . . ?
O1B C8B H8B1 109.5 . . ?
C9B C8B H8B1 109.5 . . ?
O1B C8B H8B2 109.5 . . ?
C9B C8B H8B2 109.5 . . ?
H8B1 C8B H8B2 108.1 . . ?
C8B C9B N2B 111.0(8) . . ?
C8B C9B H9B1 109.4 . . ?
N2B C9B H9B1 109.4 . . ?
C8B C9B H9B2 109.4 . . ?
N2B C9B H9B2 109.4 . . ?
H9B1 C9B H9B2 108.0 . . ?
O2 S1 O3 115.53(18) . . ?
O2 S1 N3 110.70(16) . . ?
O3 S1 N3 111.11(19) . . ?
O2 S1 C11 110.2(2) . . ?
O3 S1 C11 110.51(17) . . ?
N3 S1 C11 97.4(2) . . ?
C17 N3 S1 110.0(3) . . ?
C12 C11 C16 122.7(4) . . ?
C12 C11 S1 131.1(3) . . ?
C16 C11 S1 106.2(3) . . ?
C11 C12 C13 117.7(4) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 H12 121.1 . . ?
C14 C13 C12 119.7(5) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C15 C14 C13 120.8(5) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 119.7(4) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C11 C16 C15 119.3(4) . . ?
C11 C16 C17 111.3(4) . . ?
C15 C16 C17 129.3(4) . . ?
O4 C17 N3 123.6(4) . . ?
O4 C17 C16 121.5(4) . . ?
N3 C17 C16 114.9(3) . . ?

_refine_diff_density_max         0.396
_refine_diff_density_min         -0.651
_refine_diff_density_rms         0.066



####################################################################### 
# 
# 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_PiPYH_I3
_database_code_depnum_ccdc_archive 'CCDC 2255960'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        OID-012-5
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H14 N2, C10 H15 N2, I3'
_chemical_formula_sum            'C20 H29 I3 N4'
_chemical_formula_weight         706.17

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   13.1946(7)
_cell_length_b                   15.4088(10)
_cell_length_c                   19.6477(14)
_cell_angle_alpha                71.888(2)
_cell_angle_beta                 80.519(3)
_cell_angle_gamma                70.237(2)
_cell_volume                     3565.1(4)
_cell_formula_units_Z            6
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5633
_cell_measurement_theta_min      2.6310
_cell_measurement_theta_max      27.3830

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.973
_exptl_crystal_F_000             2016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    3.958
_shelx_estimated_absorpt_T_min   0.463
_shelx_estimated_absorpt_T_max   0.505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.76514
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.833
_oxdiff_exptl_absorpt_empirical_full_max 1.346
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27685
_diffrn_reflns_av_unetI/netI     0.1440
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.186
_diffrn_reflns_theta_max         26.250
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             14353
_reflns_number_gt                7527
_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       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0084P)²] 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         14353
_refine_ls_number_parameters     730
_refine_ls_number_restraints     144
_refine_ls_R_factor_all          0.1227
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.1245
_refine_ls_wR_factor_gt          0.0868
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.993
_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 0.48003(6) 1.12478(6) 0.09529(4) 0.0521(2) Uani 1 1 d . . . . .
I2 I 0.47688(5) 1.08238(5) 0.24956(4) 0.03128(18) Uani 1 1 d . . . . .
I3 I 0.47680(5) 1.03154(5) 0.40632(4) 0.0407(2) Uani 1 1 d . . . . .
I4 I 0.82309(6) 0.42389(5) 0.51015(4) 0.0395(2) Uani 1 1 d . . . . .
I5 I 0.81406(5) 0.37867(4) 0.66648(4) 0.02820(17) Uani 1 1 d . . . . .
I6 I 0.82372(5) 0.33309(5) 0.82149(4) 0.0396(2) Uani 1 1 d . . . . .
I7 I 0.85033(6) 0.27762(5) 1.01786(4) 0.0388(2) Uani 1 1 d . . . . .
I8 I 0.88351(5) 0.24866(4) 1.16731(4) 0.02776(17) Uani 1 1 d . . . . .
I9 I 0.91209(5) 0.22826(5) 1.31634(4) 0.0396(2) Uani 1 1 d . . . . .
N1 N 0.8391(7) 1.0133(6) 0.0183(4) 0.034(2) Uani 1 1 d . . . . .
N2 N 0.7695(6) 1.0474(6) -0.1934(4) 0.031(2) Uani 1 1 d . . . . .
C1 C 0.7266(7) 1.0946(7) -0.0811(5) 0.031(2) Uani 1 1 d . . . . .
H1 H 0.663860 1.144587 -0.099408 0.037 Uiso 1 1 calc R U . . .
C2 C 0.7549(8) 1.0823(7) -0.0141(5) 0.031(2) Uani 1 1 d . . . . .
H2 H 0.711204 1.126574 0.011534 0.037 Uiso 1 1 calc R U . . .
C3 C 0.8991(8) 0.9526(7) -0.0211(6) 0.039(3) Uani 1 1 d . . . . .
H3 H 0.959798 0.902253 -0.000149 0.046 Uiso 1 1 calc R U . . .
C4 C 0.8780(8) 0.9589(7) -0.0892(6) 0.032(3) Uani 1 1 d . . . . .
H4 H 0.922741 0.913138 -0.113251 0.038 Uiso 1 1 calc R U . . .
C5 C 0.7900(7) 1.0335(7) -0.1231(5) 0.028(2) Uani 1 1 d . . . . .
C6 C 0.6789(9) 1.1232(8) -0.2257(6) 0.058(4) Uani 1 1 d . . . . .
H6A H 0.664051 1.178095 -0.205622 0.070 Uiso 1 1 calc R U . . .
H6B H 0.614415 1.100786 -0.214239 0.070 Uiso 1 1 calc R U . . .
C7 C 0.6994(9) 1.1558(7) -0.3067(6) 0.043(3) Uani 1 1 d . . . . .
H7A H 0.633056 1.203990 -0.327990 0.052 Uiso 1 1 calc R U . . .
H7B H 0.757159 1.186693 -0.318253 0.052 Uiso 1 1 calc R U . . .
C8 C 0.7324(8) 1.0724(7) -0.3393(5) 0.035(3) Uani 1 1 d . . . . .
H8A H 0.671369 1.046376 -0.333187 0.041 Uiso 1 1 calc R U . . .
H8B H 0.751088 1.094710 -0.391333 0.041 Uiso 1 1 calc R U . . .
C9 C 0.8272(8) 0.9957(7) -0.3038(5) 0.035(3) Uani 1 1 d . . . . .
H9A H 0.845080 0.939811 -0.323232 0.042 Uiso 1 1 calc R U . . .
H9B H 0.890412 1.019794 -0.314684 0.042 Uiso 1 1 calc R U . . .
C10 C 0.8052(8) 0.9648(7) -0.2246(5) 0.030(3) Uani 1 1 d . . . . .
H10A H 0.748513 0.932722 -0.213450 0.037 Uiso 1 1 calc R U . . .
H10B H 0.871482 0.917740 -0.202379 0.037 Uiso 1 1 calc R U . . .
N3 N 0.8669(6) 0.9838(5) 0.1561(4) 0.0260(18) Uani 1 1 d . . . . .
H3N H 0.860627 0.998213 0.105544 0.031 Uiso 1 1 calc R U . . .
N4 N 0.8882(6) 0.9179(6) 0.3758(4) 0.027(2) Uani 1 1 d . . . . .
C11 C 0.9676(7) 0.8960(7) 0.2585(5) 0.024(2) Uani 1 1 d . . . . .
H11 H 1.031874 0.849973 0.278242 0.029 Uiso 1 1 calc R U . . .
C12 C 0.9569(7) 0.9209(6) 0.1871(5) 0.028(2) Uani 1 1 d . . . . .
H12 H 1.015285 0.892730 0.157493 0.033 Uiso 1 1 calc R U . . .
C13 C 0.7870(8) 1.0254(7) 0.1973(5) 0.028(2) Uani 1 1 d . . . . .
H13 H 0.725002 1.072127 0.175014 0.033 Uiso 1 1 calc R U . . .
C14 C 0.7893(7) 1.0045(6) 0.2705(5) 0.023(2) Uani 1 1 d . . . . .
H14 H 0.728614 1.034226 0.297850 0.027 Uiso 1 1 calc R U . . .
C15 C 0.8819(7) 0.9390(7) 0.3048(5) 0.021(2) Uani 1 1 d . . . . .
C16 C 0.9758(7) 0.8375(6) 0.4157(5) 0.026(2) Uani 1 1 d . . . . .
H16A H 1.035786 0.815350 0.381430 0.031 Uiso 1 1 calc R U . . .
H16B H 0.948062 0.783080 0.441995 0.031 Uiso 1 1 calc R U . . .
C17 C 1.0170(8) 0.8699(7) 0.4682(5) 0.030(3) Uani 1 1 d . . . . .
H17A H 1.072811 0.814894 0.495952 0.036 Uiso 1 1 calc R U . . .
H17B H 1.051040 0.919970 0.441292 0.036 Uiso 1 1 calc R U . . .
C18 C 0.9276(8) 0.9092(7) 0.5194(5) 0.031(2) Uani 1 1 d . . . . .
H18A H 0.956248 0.934672 0.550025 0.038 Uiso 1 1 calc R U . . .
H18B H 0.899881 0.856985 0.551060 0.038 Uiso 1 1 calc R U . . .
C19 C 0.8360(8) 0.9886(7) 0.4785(5) 0.031(2) Uani 1 1 d . . . . .
H19A H 0.860251 1.045496 0.453813 0.037 Uiso 1 1 calc R U . . .
H19B H 0.774229 1.007403 0.512707 0.037 Uiso 1 1 calc R U . . .
C20 C 0.7996(7) 0.9555(7) 0.4229(5) 0.029(2) Uani 1 1 d . . . . .
H20A H 0.764871 0.905344 0.448295 0.034 Uiso 1 1 calc R U . . .
H20B H 0.745191 1.010383 0.393882 0.034 Uiso 1 1 calc R U . . .
N5 N 0.7896(6) 0.7142(6) 0.4226(5) 0.031(2) Uani 1 1 d . . . . .
N6 N 0.7555(6) 0.7826(5) 0.2001(4) 0.0250(18) Uani 1 1 d . . . . .
C21 C 0.6858(8) 0.8030(7) 0.3188(5) 0.028(2) Uani 1 1 d . . . . .
H21 H 0.620729 0.848496 0.299910 0.034 Uiso 1 1 calc R U . . .
C22 C 0.6980(7) 0.7787(6) 0.3919(5) 0.025(2) Uani 1 1 d . . . . .
H22 H 0.640653 0.807889 0.421601 0.030 Uiso 1 1 calc R U . . .
C23 C 0.8693(8) 0.6784(7) 0.3775(5) 0.025(2) Uani 1 1 d . . . . .
H23 H 0.934662 0.634873 0.397316 0.029 Uiso 1 1 calc R U . . .
C24 C 0.8633(7) 0.6997(6) 0.3055(5) 0.022(2) Uani 1 1 d . . . . .
H24 H 0.924106 0.672468 0.277071 0.027 Uiso 1 1 calc R U . . .
C25 C 0.7671(7) 0.7622(6) 0.2723(5) 0.021(2) Uani 1 1 d . . . . .
C26 C 0.6599(7) 0.8560(7) 0.1651(5) 0.029(2) Uani 1 1 d . . . . .
H26A H 0.678476 0.915114 0.138105 0.035 Uiso 1 1 calc R U . . .
H26B H 0.601401 0.871902 0.201983 0.035 Uiso 1 1 calc R U . . .
C27 C 0.6211(8) 0.8189(7) 0.1140(5) 0.036(3) Uani 1 1 d . . . . .
H27A H 0.595110 0.764074 0.142183 0.043 Uiso 1 1 calc R U . . .
H27B H 0.559343 0.870135 0.089273 0.043 Uiso 1 1 calc R U . . .
C28 C 0.7081(8) 0.7870(7) 0.0581(5) 0.038(3) Uani 1 1 d . . . . .
H28A H 0.727070 0.843140 0.024671 0.046 Uiso 1 1 calc R U . . .
H28B H 0.681607 0.756719 0.029972 0.046 Uiso 1 1 calc R U . . .
C29 C 0.8070(8) 0.7155(7) 0.0963(5) 0.032(2) Uani 1 1 d . . . . .
H29A H 0.790554 0.655018 0.122087 0.038 Uiso 1 1 calc R U . . .
H29B H 0.867030 0.701213 0.059959 0.038 Uiso 1 1 calc R U . . .
C30 C 0.8438(7) 0.7501(7) 0.1494(5) 0.029(2) Uani 1 1 d . . . . .
H30A H 0.902488 0.697316 0.176124 0.035 Uiso 1 1 calc R U . . .
H30B H 0.873058 0.803567 0.122906 0.035 Uiso 1 1 calc R U . . .
N7 N 0.8257(6) 0.6749(5) 0.5619(4) 0.0227(19) Uani 1 1 d . . . . .
H7N H 0.811652 0.683783 0.513427 0.027 Uiso 1 1 calc R U . . .
N8 N 0.8742(5) 0.6324(5) 0.7770(4) 0.0205(17) Uani 1 1 d . . . . .
C31 C 0.9243(7) 0.5830(6) 0.6655(5) 0.023(2) Uani 1 1 d . . . . .
H31 H 0.981514 0.528718 0.686625 0.028 Uiso 1 1 calc R U . . .
C32 C 0.9036(7) 0.5985(7) 0.5970(5) 0.029(2) Uani 1 1 d . . . . .
H32 H 0.946189 0.553204 0.571995 0.034 Uiso 1 1 calc R U . . .
C33 C 0.7680(7) 0.7388(7) 0.6002(5) 0.024(2) Uani 1 1 d . . . . .
H33 H 0.714248 0.794395 0.576618 0.029 Uiso 1 1 calc R U . . .
C34 C 0.7825(7) 0.7281(7) 0.6695(5) 0.028(2) Uani 1 1 d . . . . .
H34 H 0.739484 0.775263 0.692801 0.033 Uiso 1 1 calc R U . . .
C35 C 0.8614(7) 0.6469(6) 0.7067(5) 0.0216(19) Uani 1 1 d . . . . .
C36 C 0.9651(8) 0.5513(7) 0.8133(5) 0.036(3) Uani 1 1 d . . . . .
H36A H 1.029180 0.573102 0.807749 0.043 Uiso 1 1 calc R U . . .
H36B H 0.984002 0.498712 0.790108 0.043 Uiso 1 1 calc R U . . .
C37 C 0.9352(9) 0.5142(7) 0.8922(6) 0.040(3) Uani 1 1 d . . . . .
H37A H 0.877066 0.484871 0.897579 0.048 Uiso 1 1 calc R U . . .
H37B H 0.998633 0.463604 0.915469 0.048 Uiso 1 1 calc R U . . .
C38 C 0.8977(7) 0.5923(7) 0.9296(5) 0.033(3) Uani 1 1 d . . . . .
H38A H 0.957397 0.618342 0.928004 0.039 Uiso 1 1 calc R U . . .
H38B H 0.876055 0.565908 0.980504 0.039 Uiso 1 1 calc R U . . .
C39 C 0.8001(8) 0.6740(7) 0.8920(5) 0.035(3) Uani 1 1 d . . . . .
H39A H 0.737352 0.650008 0.898821 0.042 Uiso 1 1 calc R U . . .
H39B H 0.779665 0.728009 0.913849 0.042 Uiso 1 1 calc R U . . .
C40 C 0.8300(8) 0.7087(6) 0.8123(5) 0.027(2) Uani 1 1 d . . . . .
H40A H 0.764909 0.755134 0.788376 0.032 Uiso 1 1 calc R U . . .
H40B H 0.883744 0.742941 0.806073 0.032 Uiso 1 1 calc R U . . .
N9 N 0.5216(6) 0.6301(6) 0.8517(4) 0.0254(19) Uani 1 1 d . . . . .
N10 N 0.4774(6) 0.6857(6) 0.6346(4) 0.027(2) Uani 1 1 d . . . . .
C41 C 0.4119(8) 0.7104(7) 0.7521(6) 0.030(3) Uani 1 1 d . . . . .
H41 H 0.345059 0.753286 0.734170 0.036 Uiso 1 1 calc R U . . .
C42 C 0.4272(8) 0.6900(6) 0.8228(5) 0.028(2) Uani 1 1 d . . . . .
H42 H 0.370197 0.718393 0.853010 0.034 Uiso 1 1 calc R U . . .
C43 C 0.5999(8) 0.5907(7) 0.8072(5) 0.028(2) Uani 1 1 d . . . . .
H43 H 0.666491 0.549254 0.826393 0.034 Uiso 1 1 calc R U . . .
C44 C 0.5891(7) 0.6067(7) 0.7361(5) 0.029(2) Uani 1 1 d . . . . .
H44 H 0.646673 0.575585 0.707558 0.034 Uiso 1 1 calc R U . . .
C45 C 0.4927(7) 0.6695(6) 0.7050(5) 0.023(2) Uani 1 1 d . . . . .
C46 C 0.3860(8) 0.7624(7) 0.5972(5) 0.031(3) Uani 1 1 d . . . . .
H46A H 0.410395 0.818361 0.569534 0.037 Uiso 1 1 calc R U . . .
H46B H 0.328289 0.783118 0.633208 0.037 Uiso 1 1 calc R U . . .
C47 C 0.3407(8) 0.7299(7) 0.5468(5) 0.029(3) Uani 1 1 d . . . . .
H47A H 0.310115 0.677875 0.574841 0.035 Uiso 1 1 calc R U . . .
H47B H 0.281948 0.784055 0.521304 0.035 Uiso 1 1 calc R U . . .
C48 C 0.4279(8) 0.6943(8) 0.4929(6) 0.048(3) Uani 1 1 d . . . . .
H48A H 0.398392 0.668852 0.462778 0.058 Uiso 1 1 calc R U . . .
H48B H 0.452640 0.748202 0.461197 0.058 Uiso 1 1 calc R U . . .
C49 C 0.5213(8) 0.6172(7) 0.5304(5) 0.034(3) Uani 1 1 d . . . . .
H49A H 0.579874 0.598181 0.494281 0.041 Uiso 1 1 calc R U . . .
H49B H 0.498496 0.560146 0.557290 0.041 Uiso 1 1 calc R U . . .
C50 C 0.5635(7) 0.6504(7) 0.5815(5) 0.033(3) Uani 1 1 d . . . . .
H50A H 0.622243 0.596592 0.607336 0.039 Uiso 1 1 calc R U . . .
H50B H 0.594070 0.702571 0.553763 0.039 Uiso 1 1 calc R U . . .
N11 N 0.5484(6) 0.5914(5) 0.9927(4) 0.0278(19) Uani 1 1 d . . . . .
H11N H 0.535425 0.601871 0.943660 0.033 Uiso 1 1 calc R U . . .
N12 N 0.6047(6) 0.5503(6) 1.2059(4) 0.029(2) Uani 1 1 d . . . . .
C51 C 0.6630(7) 0.5147(6) 1.0907(5) 0.025(2) Uani 1 1 d . . . . .
H51 H 0.730350 0.471303 1.107437 0.030 Uiso 1 1 calc R U . . .
C52 C 0.6399(7) 0.5318(6) 1.0217(5) 0.025(2) Uani 1 1 d . . . . .
H52 H 0.693254 0.498750 0.992032 0.030 Uiso 1 1 calc R U . . .
C53 C 0.4757(7) 0.6355(7) 1.0373(5) 0.027(2) Uani 1 1 d . . . . .
H53 H 0.409844 0.679140 1.018195 0.033 Uiso 1 1 calc R U . . .
C54 C 0.4879(7) 0.6233(6) 1.1076(5) 0.028(2) Uani 1 1 d . . . . .
H54 H 0.430905 0.655787 1.135700 0.033 Uiso 1 1 calc R U . . .
C55 C 0.5844(7) 0.5629(6) 1.1381(5) 0.022(2) Uani 1 1 d . . . . .
C56 C 0.7019(7) 0.4812(7) 1.2412(5) 0.030(2) Uani 1 1 d . . . . .
H56A H 0.758201 0.461487 1.204128 0.036 Uiso 1 1 calc R U . . .
H56B H 0.684181 0.423286 1.272289 0.036 Uiso 1 1 calc R U . . .
C57 C 0.7452(8) 0.5217(7) 1.2851(5) 0.031(2) Uani 1 1 d . . . . .
H57A H 0.770788 0.575009 1.253122 0.037 Uiso 1 1 calc R U . . .
H57B H 0.807769 0.471636 1.309655 0.037 Uiso 1 1 calc R U . . .
C58 C 0.6602(8) 0.5590(7) 1.3414(5) 0.035(3) Uani 1 1 d . . . . .
H58A H 0.642353 0.504617 1.378169 0.042 Uiso 1 1 calc R U . . .
H58B H 0.689001 0.592417 1.365610 0.042 Uiso 1 1 calc R U . . .
C59 C 0.5591(8) 0.6280(6) 1.3042(5) 0.031(2) Uani 1 1 d . . . . .
H59A H 0.501754 0.647064 1.340950 0.037 Uiso 1 1 calc R U . . .
H59B H 0.575255 0.686590 1.273002 0.037 Uiso 1 1 calc R U . . .
C60 C 0.5178(8) 0.5841(7) 1.2592(5) 0.028(2) Uani 1 1 d . . . . .
H60A H 0.494148 0.529527 1.290781 0.034 Uiso 1 1 calc R U . . .
H60B H 0.454918 0.632541 1.233819 0.034 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 I2 2.8916(11) . ?
I2 I3 2.9325(11) . ?
I4 I5 2.9221(10) . ?
I5 I6 2.9193(10) . ?
I7 I8 2.9137(10) . ?
I8 I9 2.9200(10) . ?
N1 C2 1.335(11) . ?
N1 C3 1.359(13) . ?
N2 C5 1.386(11) . ?
N2 C6 1.429(11) . ?
N2 C10 1.485(11) . ?
C1 C2 1.366(12) . ?
C1 C5 1.412(13) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C4 1.379(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.411(12) . ?
C4 H4 0.9500 . ?
C6 C7 1.520(15) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.514(13) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.492(12) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.489(13) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
N3 C13 1.326(11) . ?
N3 C12 1.346(10) . ?
N3 H3N 0.9600 . ?
N4 C15 1.339(11) . ?
N4 C20 1.442(11) . ?
N4 C16 1.487(10) . ?
C11 C12 1.354(12) . ?
C11 C15 1.441(12) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.377(12) . ?
C13 H13 0.9500 . ?
C14 C15 1.406(11) . ?
C14 H14 0.9500 . ?
C16 C17 1.516(11) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.508(13) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.520(12) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.540(11) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
N5 C23 1.342(12) . ?
N5 C22 1.366(10) . ?
N6 C25 1.377(11) . ?
N6 C30 1.461(11) . ?
N6 C26 1.477(10) . ?
C21 C22 1.389(12) . ?
C21 C25 1.399(13) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.357(12) . ?
C23 H23 0.9500 . ?
C24 C25 1.422(11) . ?
C24 H24 0.9500 . ?
C26 C27 1.522(12) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.518(13) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.522(12) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.514(12) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
N7 C32 1.352(10) . ?
N7 C33 1.371(11) . ?
N7 H7N 0.9600 . ?
N8 C35 1.358(11) . ?
N8 C40 1.454(11) . ?
N8 C36 1.491(10) . ?
C31 C32 1.349(12) . ?
C31 C35 1.427(12) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C34 1.356(12) . ?
C33 H33 0.9500 . ?
C34 C35 1.409(11) . ?
C34 H34 0.9500 . ?
C36 C37 1.513(13) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.504(13) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 C39 1.557(12) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C40 1.521(12) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
N9 C43 1.345(12) . ?
N9 C42 1.362(11) . ?
N10 C45 1.363(11) . ?
N10 C46 1.477(10) . ?
N10 C50 1.489(12) . ?
C41 C42 1.358(12) . ?
C41 C45 1.405(13) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C43 C44 1.363(12) . ?
C43 H43 0.9500 . ?
C44 C45 1.408(11) . ?
C44 H44 0.9500 . ?
C46 C47 1.515(11) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 C48 1.509(14) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 C49 1.496(12) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C49 C50 1.509(12) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
N11 C52 1.334(10) . ?
N11 C53 1.343(12) . ?
N11 H11N 0.9600 . ?
N12 C55 1.343(11) . ?
N12 C56 1.473(10) . ?
N12 C60 1.491(12) . ?
C51 C52 1.362(12) . ?
C51 C55 1.445(13) . ?
C51 H51 0.9500 . ?
C52 H52 0.9500 . ?
C53 C54 1.363(12) . ?
C53 H53 0.9500 . ?
C54 C55 1.397(11) . ?
C54 H54 0.9500 . ?
C56 C57 1.482(11) . ?
C56 H56A 0.9900 . ?
C56 H56B 0.9900 . ?
C57 C58 1.538(13) . ?
C57 H57A 0.9900 . ?
C57 H57B 0.9900 . ?
C58 C59 1.524(11) . ?
C58 H58A 0.9900 . ?
C58 H58B 0.9900 . ?
C59 C60 1.522(11) . ?
C59 H59A 0.9900 . ?
C59 H59B 0.9900 . ?
C60 H60A 0.9900 . ?
C60 H60B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I1 I2 I3 177.81(3) . . ?
I6 I5 I4 175.25(3) . . ?
I7 I8 I9 177.58(3) . . ?
C2 N1 C3 114.7(9) . . ?
C5 N2 C6 120.8(9) . . ?
C5 N2 C10 119.7(8) . . ?
C6 N2 C10 113.9(8) . . ?
C2 C1 C5 120.4(9) . . ?
C2 C1 H1 119.8 . . ?
C5 C1 H1 119.8 . . ?
N1 C2 C1 125.4(10) . . ?
N1 C2 H2 117.3 . . ?
C1 C2 H2 117.3 . . ?
N1 C3 C4 124.6(9) . . ?
N1 C3 H3 117.7 . . ?
C4 C3 H3 117.7 . . ?
C3 C4 C5 119.9(10) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
N2 C5 C4 122.4(9) . . ?
N2 C5 C1 122.6(8) . . ?
C4 C5 C1 115.0(9) . . ?
N2 C6 C7 111.2(10) . . ?
N2 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
N2 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C6 111.4(9) . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C9 C8 C7 110.1(8) . . ?
C9 C8 H8A 109.6 . . ?
C7 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.2 . . ?
C10 C9 C8 111.4(9) . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
N2 C10 C9 111.5(8) . . ?
N2 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
N2 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C13 N3 C12 118.4(8) . . ?
C13 N3 H3N 120.8 . . ?
C12 N3 H3N 120.8 . . ?
C15 N4 C20 122.9(7) . . ?
C15 N4 C16 123.2(8) . . ?
C20 N4 C16 112.4(8) . . ?
C12 C11 C15 120.2(8) . . ?
C12 C11 H11 119.9 . . ?
C15 C11 H11 119.9 . . ?
N3 C12 C11 122.7(10) . . ?
N3 C12 H12 118.6 . . ?
C11 C12 H12 118.6 . . ?
N3 C13 C14 123.4(9) . . ?
N3 C13 H13 118.3 . . ?
C14 C13 H13 118.3 . . ?
C13 C14 C15 119.8(9) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
N4 C15 C14 121.8(9) . . ?
N4 C15 C11 122.9(8) . . ?
C14 C15 C11 115.3(8) . . ?
N4 C16 C17 110.2(7) . . ?
N4 C16 H16A 109.6 . . ?
C17 C16 H16A 109.6 . . ?
N4 C16 H16B 109.6 . . ?
C17 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
C18 C17 C16 111.9(8) . . ?
C18 C17 H17A 109.2 . . ?
C16 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
C16 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C17 C18 C19 110.7(8) . . ?
C17 C18 H18A 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C18 C19 C20 110.9(8) . . ?
C18 C19 H19A 109.5 . . ?
C20 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 108.0 . . ?
N4 C20 C19 112.4(7) . . ?
N4 C20 H20A 109.1 . . ?
C19 C20 H20A 109.1 . . ?
N4 C20 H20B 109.1 . . ?
C19 C20 H20B 109.1 . . ?
H20A C20 H20B 107.9 . . ?
C23 N5 C22 116.0(9) . . ?
C25 N6 C30 123.3(7) . . ?
C25 N6 C26 122.0(8) . . ?
C30 N6 C26 113.4(7) . . ?
C22 C21 C25 121.6(9) . . ?
C22 C21 H21 119.2 . . ?
C25 C21 H21 119.2 . . ?
N5 C22 C21 122.3(10) . . ?
N5 C22 H22 118.9 . . ?
C21 C22 H22 118.9 . . ?
N5 C23 C24 124.8(9) . . ?
N5 C23 H23 117.6 . . ?
C24 C23 H23 117.6 . . ?
C23 C24 C25 120.7(9) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
N6 C25 C21 122.7(8) . . ?
N6 C25 C24 122.8(9) . . ?
C21 C25 C24 114.4(9) . . ?
N6 C26 C27 110.2(8) . . ?
N6 C26 H26A 109.6 . . ?
C27 C26 H26A 109.6 . . ?
N6 C26 H26B 109.6 . . ?
C27 C26 H26B 109.6 . . ?
H26A C26 H26B 108.1 . . ?
C28 C27 C26 113.2(8) . . ?
C28 C27 H27A 108.9 . . ?
C26 C27 H27A 108.9 . . ?
C28 C27 H27B 108.9 . . ?
C26 C27 H27B 108.9 . . ?
H27A C27 H27B 107.8 . . ?
C27 C28 C29 108.6(8) . . ?
C27 C28 H28A 110.0 . . ?
C29 C28 H28A 110.0 . . ?
C27 C28 H28B 110.0 . . ?
C29 C28 H28B 110.0 . . ?
H28A C28 H28B 108.4 . . ?
C30 C29 C28 113.9(9) . . ?
C30 C29 H29A 108.8 . . ?
C28 C29 H29A 108.8 . . ?
C30 C29 H29B 108.8 . . ?
C28 C29 H29B 108.8 . . ?
H29A C29 H29B 107.7 . . ?
N6 C30 C29 111.7(8) . . ?
N6 C30 H30A 109.3 . . ?
C29 C30 H30A 109.3 . . ?
N6 C30 H30B 109.3 . . ?
C29 C30 H30B 109.3 . . ?
H30A C30 H30B 107.9 . . ?
C32 N7 C33 115.6(8) . . ?
C32 N7 H7N 122.2 . . ?
C33 N7 H7N 122.2 . . ?
C35 N8 C40 122.1(7) . . ?
C35 N8 C36 120.0(8) . . ?
C40 N8 C36 114.3(7) . . ?
C32 C31 C35 121.0(8) . . ?
C32 C31 H31 119.5 . . ?
C35 C31 H31 119.5 . . ?
C31 C32 N7 123.7(10) . . ?
C31 C32 H32 118.1 . . ?
N7 C32 H32 118.1 . . ?
C34 C33 N7 124.5(9) . . ?
C34 C33 H33 117.8 . . ?
N7 C33 H33 117.8 . . ?
C33 C34 C35 119.9(10) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 H34 120.1 . . ?
N8 C35 C34 121.0(9) . . ?
N8 C35 C31 123.7(8) . . ?
C34 C35 C31 115.2(8) . . ?
N8 C36 C37 111.1(8) . . ?
N8 C36 H36A 109.4 . . ?
C37 C36 H36A 109.4 . . ?
N8 C36 H36B 109.4 . . ?
C37 C36 H36B 109.4 . . ?
H36A C36 H36B 108.0 . . ?
C38 C37 C36 112.1(8) . . ?
C38 C37 H37A 109.2 . . ?
C36 C37 H37A 109.2 . . ?
C38 C37 H37B 109.2 . . ?
C36 C37 H37B 109.2 . . ?
H37A C37 H37B 107.9 . . ?
C37 C38 C39 109.8(8) . . ?
C37 C38 H38A 109.7 . . ?
C39 C38 H38A 109.7 . . ?
C37 C38 H38B 109.7 . . ?
C39 C38 H38B 109.7 . . ?
H38A C38 H38B 108.2 . . ?
C40 C39 C38 109.8(8) . . ?
C40 C39 H39A 109.7 . . ?
C38 C39 H39A 109.7 . . ?
C40 C39 H39B 109.7 . . ?
C38 C39 H39B 109.7 . . ?
H39A C39 H39B 108.2 . . ?
N8 C40 C39 114.0(8) . . ?
N8 C40 H40A 108.8 . . ?
C39 C40 H40A 108.8 . . ?
N8 C40 H40B 108.8 . . ?
C39 C40 H40B 108.8 . . ?
H40A C40 H40B 107.6 . . ?
C43 N9 C42 117.0(8) . . ?
C45 N10 C46 123.3(8) . . ?
C45 N10 C50 124.2(7) . . ?
C46 N10 C50 110.2(7) . . ?
C42 C41 C45 121.5(9) . . ?
C42 C41 H41 119.3 . . ?
C45 C41 H41 119.3 . . ?
C41 C42 N9 122.2(10) . . ?
C41 C42 H42 118.9 . . ?
N9 C42 H42 118.9 . . ?
N9 C43 C44 123.8(9) . . ?
N9 C43 H43 118.1 . . ?
C44 C43 H43 118.1 . . ?
C43 C44 C45 120.0(10) . . ?
C43 C44 H44 120.0 . . ?
C45 C44 H44 120.0 . . ?
N10 C45 C41 122.5(8) . . ?
N10 C45 C44 122.0(10) . . ?
C41 C45 C44 115.5(9) . . ?
N10 C46 C47 112.0(8) . . ?
N10 C46 H46A 109.2 . . ?
C47 C46 H46A 109.2 . . ?
N10 C46 H46B 109.2 . . ?
C47 C46 H46B 109.2 . . ?
H46A C46 H46B 107.9 . . ?
C48 C47 C46 110.6(8) . . ?
C48 C47 H47A 109.5 . . ?
C46 C47 H47A 109.5 . . ?
C48 C47 H47B 109.5 . . ?
C46 C47 H47B 109.5 . . ?
H47A C47 H47B 108.1 . . ?
C49 C48 C47 110.5(9) . . ?
C49 C48 H48A 109.5 . . ?
C47 C48 H48A 109.5 . . ?
C49 C48 H48B 109.5 . . ?
C47 C48 H48B 109.5 . . ?
H48A C48 H48B 108.1 . . ?
C48 C49 C50 111.4(9) . . ?
C48 C49 H49A 109.4 . . ?
C50 C49 H49A 109.4 . . ?
C48 C49 H49B 109.4 . . ?
C50 C49 H49B 109.4 . . ?
H49A C49 H49B 108.0 . . ?
N10 C50 C49 112.1(8) . . ?
N10 C50 H50A 109.2 . . ?
C49 C50 H50A 109.2 . . ?
N10 C50 H50B 109.2 . . ?
C49 C50 H50B 109.2 . . ?
H50A C50 H50B 107.9 . . ?
C52 N11 C53 114.8(8) . . ?
C52 N11 H11N 122.6 . . ?
C53 N11 H11N 122.6 . . ?
C55 N12 C56 124.6(8) . . ?
C55 N12 C60 121.9(7) . . ?
C56 N12 C60 111.5(7) . . ?
C52 C51 C55 119.6(8) . . ?
C52 C51 H51 120.2 . . ?
C55 C51 H51 120.2 . . ?
N11 C52 C51 125.1(10) . . ?
N11 C52 H52 117.4 . . ?
C51 C52 H52 117.4 . . ?
N11 C53 C54 125.8(8) . . ?
N11 C53 H53 117.1 . . ?
C54 C53 H53 117.1 . . ?
C53 C54 C55 119.9(10) . . ?
C53 C54 H54 120.1 . . ?
C55 C54 H54 120.1 . . ?
N12 C55 C54 123.6(9) . . ?
N12 C55 C51 121.7(8) . . ?
C54 C55 C51 114.8(9) . . ?
N12 C56 C57 112.3(8) . . ?
N12 C56 H56A 109.1 . . ?
C57 C56 H56A 109.1 . . ?
N12 C56 H56B 109.1 . . ?
C57 C56 H56B 109.1 . . ?
H56A C56 H56B 107.9 . . ?
C56 C57 C58 112.2(8) . . ?
C56 C57 H57A 109.2 . . ?
C58 C57 H57A 109.2 . . ?
C56 C57 H57B 109.2 . . ?
C58 C57 H57B 109.2 . . ?
H57A C57 H57B 107.9 . . ?
C59 C58 C57 109.0(8) . . ?
C59 C58 H58A 109.9 . . ?
C57 C58 H58A 109.9 . . ?
C59 C58 H58B 109.9 . . ?
C57 C58 H58B 109.9 . . ?
H58A C58 H58B 108.3 . . ?
C60 C59 C58 112.4(8) . . ?
C60 C59 H59A 109.1 . . ?
C58 C59 H59A 109.1 . . ?
C60 C59 H59B 109.1 . . ?
C58 C59 H59B 109.1 . . ?
H59A C59 H59B 107.9 . . ?
N12 C60 C59 110.1(7) . . ?
N12 C60 H60A 109.6 . . ?
C59 C60 H60A 109.6 . . ?
N12 C60 H60B 109.6 . . ?
C59 C60 H60B 109.6 . . ?
H60A C60 H60B 108.1 . . ?

_refine_diff_density_max         1.652
_refine_diff_density_min         -1.709
_refine_diff_density_rms         0.234



####################################################################### 
# 
# 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_MPYH_NSac_3
_database_code_depnum_ccdc_archive 'CCDC 2255959'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        OID-039-5a
_chemical_name_common            
(NISac+4-Piperidinopyridine)+4-Morpholinopyridine
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 N O3 S, C9 H13 N2 O'
_chemical_formula_sum            'C16 H17 N3 O4 S'
_chemical_formula_weight         347.38

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.0402(6)
_cell_length_b                   13.5547(9)
_cell_length_c                   14.5596(11)
_cell_angle_alpha                98.518(3)
_cell_angle_beta                 91.675(2)
_cell_angle_gamma                91.455(2)
_cell_volume                     1567.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1487
_cell_measurement_theta_min      2.8130
_cell_measurement_theta_max      22.4340

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.234
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.81760
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.775
_oxdiff_exptl_absorpt_empirical_full_max 1.345
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11331
_diffrn_reflns_av_unetI/netI     0.2104
_diffrn_reflns_av_R_equivalents  0.0860
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.226
_diffrn_reflns_theta_max         26.249
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6297
_reflns_number_gt                2853
_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       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0760P)²+1.4595P] 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         6297
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2100
_refine_ls_R_factor_gt           0.1085
_refine_ls_wR_factor_ref         0.2709
_refine_ls_wR_factor_gt          0.2043
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
N1 N 0.2571(7) 0.1174(4) 0.4987(3) 0.0270(14) Uani 1 1 d . . . . .
H1N H 0.360496 0.096589 0.471819 0.032 Uiso 1 1 calc R U . . .
N2 N -0.1901(7) 0.2075(4) 0.6093(4) 0.0258(13) Uani 1 1 d . . . . .
O1 O -0.5195(7) 0.2569(4) 0.6666(3) 0.0440(14) Uani 1 1 d . . . . .
C1 C 0.0429(9) 0.0959(5) 0.6011(4) 0.0305(17) Uani 1 1 d . . . . .
H1 H -0.002838 0.059715 0.646051 0.037 Uiso 1 1 calc R U . . .
C2 C 0.1882(10) 0.0684(5) 0.5635(4) 0.0341(18) Uani 1 1 d . . . . .
H2 H 0.243908 0.013587 0.582660 0.041 Uiso 1 1 calc R U . . .
C3 C 0.1786(10) 0.1954(5) 0.4725(4) 0.037(2) Uani 1 1 d . . . . .
H3 H 0.227227 0.228401 0.426258 0.044 Uiso 1 1 calc R U . . .
C4 C 0.0364(9) 0.2292(5) 0.5079(4) 0.0296(17) Uani 1 1 d . . . . .
H4 H -0.010862 0.286646 0.488756 0.036 Uiso 1 1 calc R U . . .
C5 C -0.0452(9) 0.1793(5) 0.5746(4) 0.0248(16) Uani 1 1 d . . . . .
C6 C -0.2985(11) 0.1377(6) 0.6495(5) 0.048(2) Uani 1 1 d . . . . .
H6A H -0.357307 0.092282 0.598619 0.058 Uiso 1 1 calc R U . . .
H6B H -0.229302 0.096564 0.685481 0.058 Uiso 1 1 calc R U . . .
C7 C -0.4212(11) 0.1887(6) 0.7103(5) 0.047(2) Uani 1 1 d . . . . .
H7A H -0.496373 0.138151 0.731224 0.057 Uiso 1 1 calc R U . . .
H7B H -0.362524 0.225984 0.765993 0.057 Uiso 1 1 calc R U . . .
C8 C -0.4074(11) 0.3300(5) 0.6365(5) 0.046(2) Uani 1 1 d . . . . .
H8A H -0.348761 0.368111 0.691856 0.055 Uiso 1 1 calc R U . . .
H8B H -0.473622 0.377546 0.606336 0.055 Uiso 1 1 calc R U . . .
C9 C -0.2833(9) 0.2867(5) 0.5716(5) 0.0328(18) Uani 1 1 d . . . . .
H9A H -0.204195 0.339965 0.559302 0.039 Uiso 1 1 calc R U . . .
H9B H -0.339912 0.258097 0.511984 0.039 Uiso 1 1 calc R U . . .
S1 S 0.4152(2) 0.05189(13) 0.15980(11) 0.0293(5) Uani 1 1 d . . . . .
O2 O 0.3304(6) 0.1229(3) 0.1115(3) 0.0322(12) Uani 1 1 d . . . . .
O3 O 0.3828(7) -0.0520(3) 0.1216(3) 0.0422(15) Uani 1 1 d . . . . .
O4 O 0.5436(6) 0.1023(3) 0.4063(3) 0.0338(13) Uani 1 1 d . . . . .
N3 N 0.3816(7) 0.0700(4) 0.2706(3) 0.0237(13) Uani 1 1 d . . . . .
C10 C 0.6311(9) 0.0771(5) 0.1675(4) 0.0258(16) Uani 1 1 d . . . . .
C11 C 0.7498(10) 0.0792(5) 0.0999(4) 0.0321(18) Uani 1 1 d . . . . .
H11 H 0.718691 0.065408 0.035762 0.038 Uiso 1 1 calc R U . . .
C12 C 0.9110(10) 0.1014(5) 0.1277(5) 0.0355(19) Uani 1 1 d . . . . .
H12 H 0.993587 0.099881 0.082233 0.043 Uiso 1 1 calc R U . . .
C13 C 0.9589(9) 0.1268(5) 0.2226(5) 0.0360(18) Uani 1 1 d . . . . .
H13 H 1.071543 0.144348 0.240535 0.043 Uiso 1 1 calc R U . . .
C14 C 0.8386(9) 0.1257(5) 0.2896(5) 0.0319(18) Uani 1 1 d . . . . .
H14 H 0.868947 0.141381 0.353797 0.038 Uiso 1 1 calc R U . . .
C15 C 0.6745(9) 0.1016(4) 0.2618(4) 0.0261(16) Uani 1 1 d . . . . .
C16 C 0.5256(9) 0.0921(5) 0.3196(5) 0.0277(17) Uani 1 1 d . . . . .
N4 N 0.2635(8) 0.6080(4) 0.9953(3) 0.0331(16) Uani 1 1 d . . . . .
H4N H 0.159889 0.583290 0.965017 0.040 Uiso 1 1 calc R U . . .
N5 N 0.7092(8) 0.7187(4) 1.1261(4) 0.0381(16) Uani 1 1 d . . . . .
O5 O 1.0534(7) 0.7605(4) 1.1654(4) 0.0520(16) Uani 1 1 d . . . . .
C17 C 0.4798(9) 0.5956(5) 1.1055(4) 0.0259(16) Uani 1 1 d . . . . .
H17 H 0.526051 0.560629 1.151622 0.031 Uiso 1 1 calc R U . . .
C18 C 0.3325(9) 0.5620(5) 1.0629(4) 0.0266(17) Uani 1 1 d . . . . .
H18 H 0.276968 0.505495 1.080758 0.032 Uiso 1 1 calc R U . . .
C19 C 0.3421(10) 0.6891(5) 0.9708(4) 0.0307(18) Uani 1 1 d . . . . .
H19 H 0.293358 0.720567 0.922837 0.037 Uiso 1 1 calc R U . . .
C20 C 0.4862(9) 0.7267(5) 1.0117(4) 0.0269(17) Uani 1 1 d . . . . .
H20 H 0.535673 0.784577 0.992872 0.032 Uiso 1 1 calc R U . . .
C21 C 0.5677(10) 0.6812(5) 1.0836(4) 0.0276(17) Uani 1 1 d . . . . .
C22 C 0.8045(11) 0.6749(6) 1.1997(6) 0.052(2) Uani 1 1 d . . . . .
H22A H 0.794754 0.717705 1.260429 0.062 Uiso 1 1 calc R U . . .
H22B H 0.756915 0.607888 1.204782 0.062 Uiso 1 1 calc R U . . .
C23 C 0.9764(12) 0.6670(7) 1.1772(6) 0.060(3) Uani 1 1 d . . . . .
H23A H 1.037370 0.639508 1.227260 0.072 Uiso 1 1 calc R U . . .
H23B H 0.985568 0.619492 1.119059 0.072 Uiso 1 1 calc R U . . .
C24 C 0.9639(13) 0.8064(6) 1.0972(6) 0.061(3) Uani 1 1 d . . . . .
H24A H 0.975640 0.765926 1.035421 0.073 Uiso 1 1 calc R U . . .
H24B H 1.014813 0.873267 1.095031 0.073 Uiso 1 1 calc R U . . .
C25 C 0.7901(12) 0.8169(6) 1.1149(6) 0.060(3) Uani 1 1 d . . . . .
H25A H 0.734286 0.843577 1.062666 0.072 Uiso 1 1 calc R U . . .
H25B H 0.776909 0.865116 1.172099 0.072 Uiso 1 1 calc R U . . .
S2 S 0.0694(2) 0.54609(12) 0.65901(11) 0.0272(5) Uani 1 1 d . . . . .
O6 O 0.0892(6) 0.4429(3) 0.6218(3) 0.0336(13) Uani 1 1 d . . . . .
O7 O 0.1599(6) 0.6170(3) 0.6118(3) 0.0305(12) Uani 1 1 d . . . . .
O8 O -0.0365(6) 0.6002(3) 0.9032(3) 0.0345(13) Uani 1 1 d . . . . .
N6 N 0.1121(8) 0.5655(4) 0.7693(3) 0.0294(15) Uani 1 1 d . . . . .
C26 C -0.1448(9) 0.5740(5) 0.6635(4) 0.0267(17) Uani 1 1 d . . . . .
C27 C -0.2652(9) 0.5727(5) 0.5931(4) 0.0283(17) Uani 1 1 d . . . . .
H27 H -0.239336 0.554397 0.529698 0.034 Uiso 1 1 calc R U . . .
C28 C -0.4243(10) 0.5990(5) 0.6186(5) 0.0347(19) Uani 1 1 d . . . . .
H28 H -0.510398 0.597311 0.572200 0.042 Uiso 1 1 calc R U . . .
C29 C -0.4599(9) 0.6284(5) 0.7128(5) 0.0319(18) Uani 1 1 d . . . . .
H29 H -0.568180 0.649224 0.729708 0.038 Uiso 1 1 calc R U . . .
C30 C -0.3364(9) 0.6267(5) 0.7803(4) 0.0282(17) Uani 1 1 d . . . . .
H30 H -0.360721 0.644487 0.843995 0.034 Uiso 1 1 calc R U . . .
C31 C -0.1793(9) 0.5996(5) 0.7562(4) 0.0252(16) Uani 1 1 d . . . . .
C32 C -0.0278(10) 0.5891(5) 0.8163(4) 0.0277(17) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C3 1.341(8) . ?
N1 C2 1.354(8) . ?
N1 H1N 0.9600 . ?
N2 C5 1.326(8) . ?
N2 C6 1.466(9) . ?
N2 C9 1.486(8) . ?
O1 C7 1.436(9) . ?
O1 C8 1.447(9) . ?
C1 C2 1.343(9) . ?
C1 C5 1.444(9) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C4 1.332(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.427(9) . ?
C4 H4 0.9500 . ?
C6 C7 1.463(10) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.467(9) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
S1 O2 1.446(5) . ?
S1 O3 1.450(5) . ?
S1 N3 1.627(5) . ?
S1 C10 1.757(8) . ?
O4 C16 1.254(7) . ?
N3 C16 1.345(9) . ?
C10 C11 1.393(9) . ?
C10 C15 1.397(8) . ?
C11 C12 1.360(10) . ?
C11 H11 0.9500 . ?
C12 C13 1.412(9) . ?
C12 H12 0.9500 . ?
C13 C14 1.395(10) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(10) . ?
C14 H14 0.9500 . ?
C15 C16 1.497(10) . ?
N4 C19 1.352(9) . ?
N4 C18 1.354(8) . ?
N4 H4N 0.9600 . ?
N5 C21 1.331(9) . ?
N5 C25 1.499(10) . ?
N5 C22 1.501(9) . ?
O5 C23 1.431(10) . ?
O5 C24 1.434(9) . ?
C17 C18 1.356(9) . ?
C17 C21 1.424(9) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.340(9) . ?
C19 H19 0.9500 . ?
C20 C21 1.442(9) . ?
C20 H20 0.9500 . ?
C22 C23 1.433(11) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.435(12) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
S2 O6 1.438(4) . ?
S2 O7 1.455(5) . ?
S2 N6 1.614(5) . ?
S2 C26 1.774(7) . ?
O8 C32 1.257(7) . ?
N6 C32 1.354(9) . ?
C26 C31 1.381(8) . ?
C26 C27 1.387(9) . ?
C27 C28 1.383(9) . ?
C27 H27 0.9500 . ?
C28 C29 1.411(9) . ?
C28 H28 0.9500 . ?
C29 C30 1.380(9) . ?
C29 H29 0.9500 . ?
C30 C31 1.366(9) . ?
C30 H30 0.9500 . ?
C31 C32 1.501(10) . ?

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
C3 N1 C2 119.0(6) . . ?
C3 N1 H1N 120.5 . . ?
C2 N1 H1N 120.5 . . ?
C5 N2 C6 121.0(6) . . ?
C5 N2 C9 120.1(6) . . ?
C6 N2 C9 112.9(6) . . ?
C7 O1 C8 107.9(6) . . ?
C2 C1 C5 121.2(6) . . ?
C2 C1 H1 119.4 . . ?
C5 C1 H1 119.4 . . ?
C1 C2 N1 121.4(6) . . ?
C1 C2 H2 119.3 . . ?
N1 C2 H2 119.3 . . ?
C4 C3 N1 123.6(7) . . ?
C4 C3 H3 118.2 . . ?
N1 C3 H3 118.2 . . ?
C3 C4 C5 120.2(7) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
N2 C5 C4 122.7(6) . . ?
N2 C5 C1 122.7(6) . . ?
C4 C5 C1 114.6(6) . . ?
C7 C6 N2 112.4(6) . . ?
C7 C6 H6A 109.1 . . ?
N2 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
N2 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
O1 C7 C6 113.5(6) . . ?
O1 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
O1 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
O1 C8 C9 113.8(6) . . ?
O1 C8 H8A 108.8 . . ?
C9 C8 H8A 108.8 . . ?
O1 C8 H8B 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C8 C9 N2 111.5(6) . . ?
C8 C9 H9A 109.3 . . ?
N2 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
N2 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
O2 S1 O3 115.1(3) . . ?
O2 S1 N3 112.0(3) . . ?
O3 S1 N3 110.3(3) . . ?
O2 S1 C10 111.0(3) . . ?
O3 S1 C10 109.5(3) . . ?
N3 S1 C10 97.7(3) . . ?
C16 N3 S1 110.3(5) . . ?
C11 C10 C15 121.0(7) . . ?
C11 C10 S1 132.2(5) . . ?
C15 C10 S1 106.8(5) . . ?
C12 C11 C10 118.6(6) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C11 C12 C13 121.7(7) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C14 C13 C12 119.2(7) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C15 C14 C13 119.4(6) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C10 120.0(6) . . ?
C14 C15 C16 129.5(6) . . ?
C10 C15 C16 110.4(6) . . ?
O4 C16 N3 125.9(7) . . ?
O4 C16 C15 119.5(7) . . ?
N3 C16 C15 114.6(6) . . ?
C19 N4 C18 119.4(7) . . ?
C19 N4 H4N 120.3 . . ?
C18 N4 H4N 120.3 . . ?
C21 N5 C25 125.3(6) . . ?
C21 N5 C22 125.6(7) . . ?
C25 N5 C22 108.8(7) . . ?
C23 O5 C24 111.2(7) . . ?
C18 C17 C21 122.5(7) . . ?
C18 C17 H17 118.8 . . ?
C21 C17 H17 118.8 . . ?
N4 C18 C17 120.9(7) . . ?
N4 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C20 C19 N4 122.3(7) . . ?
C20 C19 H19 118.8 . . ?
N4 C19 H19 118.8 . . ?
C19 C20 C21 121.4(7) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
N5 C21 C17 124.4(6) . . ?
N5 C21 C20 122.1(7) . . ?
C17 C21 C20 113.5(7) . . ?
C23 C22 N5 110.3(7) . . ?
C23 C22 H22A 109.6 . . ?
N5 C22 H22A 109.6 . . ?
C23 C22 H22B 109.6 . . ?
N5 C22 H22B 109.6 . . ?
H22A C22 H22B 108.1 . . ?
O5 C23 C22 113.1(7) . . ?
O5 C23 H23A 109.0 . . ?
C22 C23 H23A 109.0 . . ?
O5 C23 H23B 109.0 . . ?
C22 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
O5 C24 C25 113.6(7) . . ?
O5 C24 H24A 108.8 . . ?
C25 C24 H24A 108.8 . . ?
O5 C24 H24B 108.8 . . ?
C25 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?
C24 C25 N5 111.1(7) . . ?
C24 C25 H25A 109.4 . . ?
N5 C25 H25A 109.4 . . ?
C24 C25 H25B 109.4 . . ?
N5 C25 H25B 109.4 . . ?
H25A C25 H25B 108.0 . . ?
O6 S2 O7 115.0(3) . . ?
O6 S2 N6 110.7(3) . . ?
O7 S2 N6 111.1(3) . . ?
O6 S2 C26 110.3(3) . . ?
O7 S2 C26 110.6(3) . . ?
N6 S2 C26 97.8(3) . . ?
C32 N6 S2 109.9(5) . . ?
C31 C26 C27 122.4(7) . . ?
C31 C26 S2 106.7(5) . . ?
C27 C26 S2 130.9(5) . . ?
C28 C27 C26 117.5(6) . . ?
C28 C27 H27 121.2 . . ?
C26 C27 H27 121.2 . . ?
C27 C28 C29 120.6(7) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 H28 119.7 . . ?
C30 C29 C28 119.6(7) . . ?
C30 C29 H29 120.2 . . ?
C28 C29 H29 120.2 . . ?
C31 C30 C29 120.4(6) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C30 C31 C26 119.4(7) . . ?
C30 C31 C32 130.1(6) . . ?
C26 C31 C32 110.5(6) . . ?
O8 C32 N6 124.6(7) . . ?
O8 C32 C31 120.6(6) . . ?
N6 C32 C31 114.8(6) . . ?

_refine_diff_density_max         1.002
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.100



####################################################################### 
# 
# 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_PPYH_NSac_1
_database_code_depnum_ccdc_archive 'CCDC 2255962'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        OID-041-2b
_chemical_name_common            
(NISac+4-Pyrrolidonopyridine)+4-Pyrrolidonopyridine
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 N O3 S, C9 H13 N2'
_chemical_formula_sum            'C16 H17 N3 O3 S'
_chemical_formula_weight         331.38

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'

_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                   7.4609(6)
_cell_length_b                   13.0907(14)
_cell_length_c                   15.3663(17)
_cell_angle_alpha                90
_cell_angle_beta                 92.576(3)
_cell_angle_gamma                90
_cell_volume                     1499.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    605
_cell_measurement_theta_min      3.0770
_cell_measurement_theta_max      23.6100

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.236
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.56263
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.756
_oxdiff_exptl_absorpt_empirical_full_max 1.611
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5823
_diffrn_reflns_av_unetI/netI     0.1826
_diffrn_reflns_av_R_equivalents  0.1058
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.654
_diffrn_reflns_theta_max         26.246
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3013
_reflns_number_gt                1613
_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       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0366P)²] 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         3013
_refine_ls_number_parameters     208
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1538
_refine_ls_R_factor_gt           0.0870
_refine_ls_wR_factor_ref         0.2056
_refine_ls_wR_factor_gt          0.1597
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.008
_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
N1 N 0.2996(5) 0.4751(4) 0.5459(2) 0.0215(11) Uani 1 1 d . . . . .
H1N H 0.237902 0.485067 0.490349 0.026 Uiso 1 1 calc R U . . .
N2 N 0.5470(5) 0.4308(4) 0.7872(2) 0.0201(10) Uani 1 1 d . . . . .
C1 C 0.4015(6) 0.5422(4) 0.6821(3) 0.0217(12) Uani 1 1 d . . . . .
H1 H 0.414680 0.598931 0.720357 0.026 Uiso 1 1 calc R U . . .
C2 C 0.3160(6) 0.5531(4) 0.6028(3) 0.0234(12) Uani 1 1 d . . . . .
H2 H 0.266395 0.617618 0.586958 0.028 Uiso 1 1 calc R U . . .
C3 C 0.3697(6) 0.3832(5) 0.5670(3) 0.0229(13) Uani 1 1 d . . . . .
H3 H 0.357968 0.329022 0.526034 0.027 Uiso 1 1 calc R U . . .
C4 C 0.4563(6) 0.3657(4) 0.6447(3) 0.0199(12) Uani 1 1 d . . . . .
H4 H 0.507049 0.300502 0.657134 0.024 Uiso 1 1 calc R U . . .
C5 C 0.4712(5) 0.4446(4) 0.7073(3) 0.0170(11) Uani 1 1 d . . . . .
C6 C 0.5767(6) 0.5115(4) 0.8517(3) 0.0232(13) Uani 1 1 d . . . . .
H6A H 0.461444 0.541373 0.868702 0.028 Uiso 1 1 calc R U . . .
H6B H 0.652793 0.566457 0.828960 0.028 Uiso 1 1 calc R U . . .
C7 C 0.6709(6) 0.4579(5) 0.9281(3) 0.0234(13) Uani 1 1 d . . . . .
H7A H 0.639730 0.489783 0.983860 0.028 Uiso 1 1 calc R U . . .
H7B H 0.802673 0.460126 0.923301 0.028 Uiso 1 1 calc R U . . .
C8 C 0.6017(7) 0.3481(5) 0.9221(3) 0.0266(14) Uani 1 1 d . . . . .
H8A H 0.482832 0.341760 0.947779 0.032 Uiso 1 1 calc R U . . .
H8B H 0.686505 0.300180 0.952111 0.032 Uiso 1 1 calc R U . . .
C9 C 0.5887(6) 0.3278(4) 0.8238(3) 0.0184(12) Uani 1 1 d . . . . .
H9A H 0.703451 0.301426 0.802874 0.022 Uiso 1 1 calc R U . . .
H9B H 0.491769 0.278467 0.808309 0.022 Uiso 1 1 calc R U . . .
S1 S 0.05600(17) 0.77896(11) 0.38424(7) 0.0213(4) Uani 1 1 d . . . . .
O1 O 0.2153(4) 0.8403(3) 0.3729(2) 0.0296(10) Uani 1 1 d . . . . .
O2 O -0.0891(4) 0.8289(3) 0.4259(2) 0.0325(10) Uani 1 1 d . . . . .
O3 O 0.1135(4) 0.5014(3) 0.39253(19) 0.0211(8) Uani 1 1 d . . . . .
N3 N 0.1068(5) 0.6711(4) 0.4309(2) 0.0196(10) Uani 1 1 d . . . . .
C10 C -0.0187(5) 0.7303(4) 0.2822(3) 0.0145(10) Uani 1 1 d . . . . .
C11 C -0.0772(6) 0.7790(4) 0.2064(3) 0.0198(12) Uani 1 1 d . . . . .
H11 H -0.090201 0.851163 0.203722 0.024 Uiso 1 1 calc R U . . .
C12 C -0.1162(6) 0.7176(4) 0.1339(3) 0.0204(12) Uani 1 1 d . . . . .
H12 H -0.152444 0.748726 0.080077 0.024 Uiso 1 1 calc R U . . .
C13 C -0.1031(6) 0.6111(4) 0.1385(3) 0.0193(12) Uani 1 1 d . . . . .
H13 H -0.134025 0.571024 0.088584 0.023 Uiso 1 1 calc R U . . .
C14 C -0.0452(5) 0.5635(4) 0.2157(3) 0.0179(11) Uani 1 1 d . . . . .
H14 H -0.036478 0.491167 0.218873 0.021 Uiso 1 1 calc R U . . .
C15 C -0.0007(5) 0.6229(4) 0.2875(3) 0.0118(9) Uani 1 1 d . . . . .
C16 C 0.0788(6) 0.5923(4) 0.3754(3) 0.0172(11) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.345(6) . ?
N1 C3 1.346(7) . ?
N1 H1N 0.9600 . ?
N2 C5 1.341(5) . ?
N2 C6 1.460(6) . ?
N2 C9 1.488(6) . ?
C1 C2 1.357(6) . ?
C1 C5 1.426(7) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C4 1.351(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.413(7) . ?
C4 H4 0.9500 . ?
C6 C7 1.513(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.529(7) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.533(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
S1 O2 1.439(3) . ?
S1 O1 1.451(4) . ?
S1 N3 1.620(4) . ?
S1 C10 1.760(4) . ?
O3 C16 1.243(6) . ?
N3 C16 1.349(6) . ?
C10 C11 1.381(6) . ?
C10 C15 1.415(7) . ?
C11 C12 1.394(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.398(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.377(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.506(6) . ?

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
C2 N1 C3 119.9(4) . . ?
C2 N1 H1N 120.1 . . ?
C3 N1 H1N 120.1 . . ?
C5 N2 C6 124.7(5) . . ?
C5 N2 C9 122.7(4) . . ?
C6 N2 C9 112.1(3) . . ?
C2 C1 C5 119.3(5) . . ?
C2 C1 H1 120.4 . . ?
C5 C1 H1 120.4 . . ?
N1 C2 C1 122.0(5) . . ?
N1 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
N1 C3 C4 122.0(5) . . ?
N1 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C5 119.8(5) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
N2 C5 C4 122.8(5) . . ?
N2 C5 C1 120.2(5) . . ?
C4 C5 C1 117.0(4) . . ?
N2 C6 C7 104.0(4) . . ?
N2 C6 H6A 111.0 . . ?
C7 C6 H6A 111.0 . . ?
N2 C6 H6B 111.0 . . ?
C7 C6 H6B 111.0 . . ?
H6A C6 H6B 109.0 . . ?
C6 C7 C8 104.2(4) . . ?
C6 C7 H7A 110.9 . . ?
C8 C7 H7A 110.9 . . ?
C6 C7 H7B 110.9 . . ?
C8 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
C7 C8 C9 103.2(4) . . ?
C7 C8 H8A 111.1 . . ?
C9 C8 H8A 111.1 . . ?
C7 C8 H8B 111.1 . . ?
C9 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
N2 C9 C8 102.6(4) . . ?
N2 C9 H9A 111.2 . . ?
C8 C9 H9A 111.2 . . ?
N2 C9 H9B 111.2 . . ?
C8 C9 H9B 111.2 . . ?
H9A C9 H9B 109.2 . . ?
O2 S1 O1 116.0(3) . . ?
O2 S1 N3 111.4(2) . . ?
O1 S1 N3 111.0(2) . . ?
O2 S1 C10 110.3(2) . . ?
O1 S1 C10 108.7(2) . . ?
N3 S1 C10 97.9(2) . . ?
C16 N3 S1 111.1(3) . . ?
C11 C10 C15 122.2(4) . . ?
C11 C10 S1 131.3(4) . . ?
C15 C10 S1 106.4(3) . . ?
C10 C11 C12 117.0(5) . . ?
C10 C11 H11 121.5 . . ?
C12 C11 H11 121.5 . . ?
C11 C12 C13 121.5(4) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 C13 C12 120.6(5) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 118.9(5) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C10 119.7(4) . . ?
C14 C15 C16 129.8(5) . . ?
C10 C15 C16 110.4(4) . . ?
O3 C16 N3 125.0(4) . . ?
O3 C16 C15 120.9(5) . . ?
N3 C16 C15 114.1(5) . . ?

_refine_diff_density_max         0.740
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.110



####################################################################### 
# 
# 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_MPYH_NSac_2
_database_code_depnum_ccdc_archive 'CCDC 2255958'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        OID-040-4a
_chemical_name_common            
(NISac+4-Morpholinopyridine)+4-Pyrrolidinopyridine
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 N O3 S, C9 H13 N2 O'
_chemical_formula_sum            'C16 H17 N3 O4 S'
_chemical_formula_weight         347.38

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'

_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                   9.8114(3)
_cell_length_b                   7.9038(2)
_cell_length_c                   10.9507(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.784(2)
_cell_angle_gamma                90
_cell_volume                     817.18(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3730
_cell_measurement_theta_min      2.4620
_cell_measurement_theta_max      28.0270

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_exptl_absorpt_coefficient_mu    0.224
_shelx_estimated_absorpt_T_min   0.906
_shelx_estimated_absorpt_T_max   0.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95624
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.865
_oxdiff_exptl_absorpt_empirical_full_max 1.175
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6043
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.474
_diffrn_reflns_theta_max         26.247
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3284
_reflns_number_gt                3100
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.997

_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       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0315P)²+0.1460P] 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 1322 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3284
_refine_ls_number_parameters     217
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0781
_refine_ls_wR_factor_gt          0.0756
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
O1 O 0.4667(3) -0.2712(3) 0.0796(2) 0.0387(6) Uani 1 1 d . . . . .
N1 N 0.6608(3) 0.5091(3) 0.3736(2) 0.0221(6) Uani 1 1 d . . . . .
H1N H 0.684269 0.619342 0.410086 0.026 Uiso 1 1 calc R U . . .
N2 N 0.5562(3) 0.0369(3) 0.2120(2) 0.0177(5) Uani 1 1 d . . . . .
C1 C 0.7079(3) 0.2838(4) 0.2492(3) 0.0204(7) Uani 1 1 d . . . . .
H1 H 0.765747 0.237624 0.200603 0.025 Uiso 1 1 calc R U . . .
C2 C 0.7376(3) 0.4396(4) 0.3020(3) 0.0221(7) Uani 1 1 d . . . . .
H2 H 0.815017 0.501280 0.287812 0.027 Uiso 1 1 calc R U . . .
C3 C 0.5509(3) 0.4228(4) 0.3936(3) 0.0240(7) Uani 1 1 d . . . . .
H3 H 0.497240 0.472318 0.444618 0.029 Uiso 1 1 calc R U . . .
C4 C 0.5141(3) 0.2673(4) 0.3433(3) 0.0204(7) Uani 1 1 d . . . . .
H4 H 0.435991 0.209762 0.359816 0.025 Uiso 1 1 calc R U . . .
C5 C 0.5917(3) 0.1894(4) 0.2659(3) 0.0174(6) Uani 1 1 d . . . . .
C6 C 0.6496(3) -0.0578(4) 0.1517(3) 0.0219(7) Uani 1 1 d . . . . .
H6A H 0.712709 -0.132239 0.215306 0.026 Uiso 1 1 calc R U . . .
H6B H 0.709600 0.022483 0.120046 0.026 Uiso 1 1 calc R U . . .
C7 C 0.5648(4) -0.1631(5) 0.0433(3) 0.0319(8) Uani 1 1 d . . . . .
H7A H 0.512590 -0.087258 -0.025548 0.038 Uiso 1 1 calc R U . . .
H7B H 0.630220 -0.232741 0.009559 0.038 Uiso 1 1 calc R U . . .
C8 C 0.3708(4) -0.1722(5) 0.1242(4) 0.0352(9) Uani 1 1 d . . . . .
H8A H 0.300037 -0.247110 0.146016 0.042 Uiso 1 1 calc R U . . .
H8B H 0.319764 -0.094883 0.055865 0.042 Uiso 1 1 calc R U . . .
C9 C 0.4450(3) -0.0698(4) 0.2392(3) 0.0224(7) Uani 1 1 d . . . . .
H9A H 0.375198 0.002726 0.264850 0.027 Uiso 1 1 calc R U . . .
H9B H 0.487776 -0.146884 0.310616 0.027 Uiso 1 1 calc R U . . .
S1 S 0.89538(7) 0.73821(8) 0.79800(6) 0.01632(17) Uani 1 1 d . . . . .
O2 O 1.0285(2) 0.6504(3) 0.8448(2) 0.0225(5) Uani 1 1 d . . . . .
O3 O 0.7988(2) 0.7210(3) 0.87580(18) 0.0236(5) Uani 1 1 d . . . . .
O4 O 0.7443(2) 0.8231(3) 0.46071(19) 0.0256(5) Uani 1 1 d . . . . .
N3 N 0.8182(3) 0.6892(3) 0.6518(2) 0.0180(6) Uani 1 1 d . . . . .
C10 C 0.9264(3) 0.9539(4) 0.7717(3) 0.0168(6) Uani 1 1 d . . . . .
C11 C 0.9908(3) 1.0781(4) 0.8560(3) 0.0215(7) Uani 1 1 d . . . . .
H11 H 1.027086 1.055567 0.944156 0.026 Uiso 1 1 calc R U . . .
C12 C 1.0001(3) 1.2386(4) 0.8057(3) 0.0251(6) Uani 1 1 d . . . . .
H12 H 1.043466 1.328092 0.860428 0.030 Uiso 1 1 calc R U . . .
C13 C 0.9467(3) 1.2691(4) 0.6765(3) 0.0261(7) Uani 1 1 d . . . . .
H13 H 0.954397 1.379316 0.644347 0.031 Uiso 1 1 calc R U . . .
C14 C 0.8820(4) 1.1413(4) 0.5931(3) 0.0250(7) Uani 1 1 d . . . . .
H14 H 0.846141 1.162532 0.504755 0.030 Uiso 1 1 calc R U . . .
C15 C 0.8718(3) 0.9825(4) 0.6428(3) 0.0177(6) Uani 1 1 d . . . . .
C16 C 0.8066(3) 0.8242(4) 0.5762(3) 0.0182(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.409(4) . ?
O1 C7 1.423(4) . ?
N1 C3 1.344(4) . ?
N1 C2 1.344(4) . ?
N1 H1N 0.9600 . ?
N2 C5 1.346(4) . ?
N2 C6 1.471(4) . ?
N2 C9 1.473(4) . ?
C1 C2 1.358(4) . ?
C1 C5 1.415(4) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C4 1.355(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.424(4) . ?
C4 H4 0.9500 . ?
C6 C7 1.502(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.508(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
S1 O3 1.4428(19) . ?
S1 O2 1.444(2) . ?
S1 N3 1.620(3) . ?
S1 C10 1.769(3) . ?
O4 C16 1.246(3) . ?
N3 C16 1.336(4) . ?
C10 C11 1.378(4) . ?
C10 C15 1.385(4) . ?
C11 C12 1.396(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.390(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.394(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.501(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
C8 O1 C7 109.2(3) . . ?
C3 N1 C2 119.3(3) . . ?
C3 N1 H1N 120.3 . . ?
C2 N1 H1N 120.3 . . ?
C5 N2 C6 122.3(3) . . ?
C5 N2 C9 122.8(2) . . ?
C6 N2 C9 112.7(2) . . ?
C2 C1 C5 120.7(3) . . ?
C2 C1 H1 119.7 . . ?
C5 C1 H1 119.7 . . ?
N1 C2 C1 122.0(3) . . ?
N1 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
N1 C3 C4 122.1(3) . . ?
N1 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C5 120.5(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
N2 C5 C1 122.5(3) . . ?
N2 C5 C4 122.1(3) . . ?
C1 C5 C4 115.4(2) . . ?
N2 C6 C7 111.0(3) . . ?
N2 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
N2 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
O1 C7 C6 112.5(3) . . ?
O1 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
O1 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
O1 C8 C9 111.8(3) . . ?
O1 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
O1 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
N2 C9 C8 110.7(3) . . ?
N2 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
O3 S1 O2 114.89(13) . . ?
O3 S1 N3 110.80(12) . . ?
O2 S1 N3 111.73(13) . . ?
O3 S1 C10 110.89(14) . . ?
O2 S1 C10 110.01(13) . . ?
N3 S1 C10 97.15(13) . . ?
C16 N3 S1 111.1(2) . . ?
C11 C10 C15 123.2(3) . . ?
C11 C10 S1 130.2(2) . . ?
C15 C10 S1 106.7(2) . . ?
C10 C11 C12 116.7(3) . . ?
C10 C11 H11 121.6 . . ?
C12 C11 H11 121.6 . . ?
C13 C12 C11 120.9(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 121.3(3) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 118.0(3) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
C14 C15 C10 120.0(3) . . ?
C14 C15 C16 129.2(3) . . ?
C10 C15 C16 110.8(2) . . ?
O4 C16 N3 124.0(3) . . ?
O4 C16 C15 121.7(3) . . ?
N3 C16 C15 114.3(2) . . ?

_refine_diff_density_max         0.206
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.042



####################################################################### 
# 
# 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_I_DMAP_2_I3_2
_database_code_depnum_ccdc_archive 'CCDC 2255964'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        TIM-165
_chemical_name_common            '(NISac+DMAP)+DMAP+NaNO3 (DCM/DMSO)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 I N4, I3'
_chemical_formula_sum            'C14 H20 I4 N4'
_chemical_formula_weight         751.94

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.9392(6)
_cell_length_b                   7.9371(7)
_cell_length_c                   9.4443(9)
_cell_angle_alpha                110.712(3)
_cell_angle_beta                 91.993(2)
_cell_angle_gamma                103.844(3)
_cell_volume                     535.80(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    1492
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      30.508

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.330
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    5.818
_shelx_estimated_absorpt_T_min   0.258
_shelx_estimated_absorpt_T_max   0.594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4616
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4223
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.326
_diffrn_reflns_theta_max         26.243
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2155
_reflns_number_gt                1866
_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0045P)²+3.1626P] 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         2155
_refine_ls_number_parameters     105
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0873
_refine_ls_wR_factor_gt          0.0830
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.500000 0.000000 0.000000 0.03410(16) Uani 1 2 d S . P . .
N1 N 0.5710(7) 0.1714(7) 0.2526(6) 0.0356(12) Uani 1 1 d . . . . .
N2 N 0.6817(6) 0.5196(8) 0.7103(6) 0.0335(12) Uani 1 1 d . . . . .
C1 C 0.7468(8) 0.4447(9) 0.4501(7) 0.0320(14) Uani 1 1 d . . . . .
H1 H 0.842299 0.553756 0.478843 0.038 Uiso 1 1 calc R U . . .
C2 C 0.7041(8) 0.3282(9) 0.3013(8) 0.0353(14) Uani 1 1 d . . . . .
H2 H 0.771352 0.358789 0.228212 0.042 Uiso 1 1 calc R U . . .
C3 C 0.4783(8) 0.1287(9) 0.3563(8) 0.0368(15) Uani 1 1 d . . . . .
H3 H 0.384046 0.018166 0.322333 0.044 Uiso 1 1 calc R U . . .
C4 C 0.5121(8) 0.2356(9) 0.5085(7) 0.0336(14) Uani 1 1 d . . . . .
H4 H 0.444369 0.197872 0.578376 0.040 Uiso 1 1 calc R U . . .
C5 C 0.6503(8) 0.4047(9) 0.5617(7) 0.0309(13) Uani 1 1 d . . . . .
C6 C 0.5878(9) 0.4682(10) 0.8255(8) 0.0390(15) Uani 1 1 d . . . . .
H6A H 0.461922 0.423631 0.789689 0.058 Uiso 1 1 calc R U . . .
H6B H 0.610556 0.577716 0.921012 0.058 Uiso 1 1 calc R U . . .
H6C H 0.627740 0.368821 0.843203 0.058 Uiso 1 1 calc R U . . .
C7 C 0.8288(9) 0.6881(10) 0.7676(8) 0.0439(17) Uani 1 1 d . . . . .
H7A H 0.824494 0.764088 0.705984 0.066 Uiso 1 1 calc R U . . .
H7B H 0.939068 0.652375 0.760901 0.066 Uiso 1 1 calc R U . . .
H7C H 0.821455 0.760725 0.874316 0.066 Uiso 1 1 calc R U . . .
I2 I 0.98985(6) 0.73746(7) 1.18869(5) 0.04826(16) Uani 1 1 d . . . . .
I3 I 1.000000 1.000000 1.500000 0.03783(17) Uani 1 2 d S . P . .


_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 N1 2.259(6) 2_655 ?
I1 N1 2.259(6) . ?
N1 C3 1.335(8) . ?
N1 C2 1.345(8) . ?
N2 C5 1.351(8) . ?
N2 C6 1.459(8) . ?
N2 C7 1.464(8) . ?
C1 C2 1.357(9) . ?
C1 C5 1.406(9) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C4 1.364(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.427(8) . ?
C4 H4 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
I2 I3 2.9262(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 I1 N1 180.0 2_655 . ?
C3 N1 C2 118.0(6) . . ?
C3 N1 I1 122.1(4) . . ?
C2 N1 I1 119.7(4) . . ?
C5 N2 C6 121.7(5) . . ?
C5 N2 C7 121.5(5) . . ?
C6 N2 C7 116.2(5) . . ?
C2 C1 C5 120.2(5) . . ?
C2 C1 H1 119.9 . . ?
C5 C1 H1 119.9 . . ?
N1 C2 C1 123.0(6) . . ?
N1 C2 H2 118.5 . . ?
C1 C2 H2 118.5 . . ?
N1 C3 C4 123.3(6) . . ?
N1 C3 H3 118.3 . . ?
C4 C3 H3 118.3 . . ?
C3 C4 C5 119.4(6) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N2 C5 C1 122.9(6) . . ?
N2 C5 C4 121.1(6) . . ?
C1 C5 C4 115.9(6) . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
I2 I3 I2 180.0 . 2_778 ?

_refine_diff_density_max         1.513
_refine_diff_density_min         -1.544
_refine_diff_density_rms         0.153



####################################################################### 
# 
# 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_I_DMAP_2_I3
_database_code_depnum_ccdc_archive 'CCDC 2255965'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        OID-009-1
_chemical_name_common            (NISac+DMAP)+DMAP
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 I N4, I3, C H2 Cl2'
_chemical_formula_sum            'C15 H22 Cl2 I4 N4'
_chemical_formula_weight         836.86

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_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'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   9.7430(4)
_cell_length_b                   9.7275(5)
_cell_length_c                   12.9505(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.585(2)
_cell_angle_gamma                90
_cell_volume                     1223.46(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    2570
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      28.700

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.272
_exptl_crystal_F_000             772
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    5.319
_shelx_estimated_absorpt_T_min   0.338
_shelx_estimated_absorpt_T_max   0.465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4126
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6365
_diffrn_reflns_av_unetI/netI     0.0682
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.097
_diffrn_reflns_theta_max         26.250
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2599
_reflns_number_gt                1973
_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0129P)²+4.0806P] 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         2599
_refine_ls_number_parameters     132
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1013
_refine_ls_wR_factor_gt          0.0947
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.073
_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 0.30464(6) 0.750000 0.30924(5) 0.03032(18) Uani 1 2 d S T P . .
N1 N 0.0920(8) 0.750000 0.3683(6) 0.0305(16) Uani 1 2 d S T P . .
N2 N -0.2935(7) 0.750000 0.4821(6) 0.0313(17) Uani 1 2 d S T P . .
N3 N 0.5154(7) 0.750000 0.2513(6) 0.0314(18) Uani 1 2 d S T P . .
N4 N 0.8986(7) 0.750000 0.1314(6) 0.0322(18) Uani 1 2 d S T P . .
C1 C 0.0277(7) 0.6312(7) 0.3862(5) 0.0334(14) Uani 1 1 d . . . . .
H1 H 0.072333 0.547153 0.372437 0.040 Uiso 1 1 calc R U . . .
C2 C -0.0988(6) 0.6267(7) 0.4233(5) 0.0312(14) Uani 1 1 d . . . . .
H2 H -0.141884 0.540701 0.433607 0.037 Uiso 1 1 calc R U . . .
C3 C -0.1657(8) 0.750000 0.4464(7) 0.0257(18) Uani 1 2 d S T P . .
C4 C -0.3581(7) 0.6217(7) 0.5118(6) 0.0418(18) Uani 1 1 d . . . . .
H4A H -0.349690 0.552683 0.457540 0.063 Uiso 1 1 calc R U . . .
H4B H -0.455735 0.638191 0.520594 0.063 Uiso 1 1 calc R U . . .
H4C H -0.312273 0.588344 0.577116 0.063 Uiso 1 1 calc R U . . .
C5 C 0.5791(7) 0.8687(7) 0.2318(5) 0.0341(16) Uani 1 1 d . . . . .
H5 H 0.534432 0.952905 0.245125 0.041 Uiso 1 1 calc R U . . .
C6 C 0.7053(6) 0.8726(7) 0.1935(5) 0.0337(15) Uani 1 1 d . . . . .
H6 H 0.746996 0.959029 0.182022 0.040 Uiso 1 1 calc R U . . .
C7 C 0.7757(8) 0.750000 0.1704(6) 0.028(2) Uani 1 2 d S T P . .
C8 C 0.9652(7) 0.8778(8) 0.1035(6) 0.0459(19) Uani 1 1 d . . . . .
H8A H 0.948733 0.948911 0.154621 0.069 Uiso 1 1 calc R U . . .
H8B H 0.927047 0.907638 0.034806 0.069 Uiso 1 1 calc R U . . .
H8C H 1.064478 0.862500 0.102223 0.069 Uiso 1 1 calc R U . . .
I2 I -0.29450(8) 0.250000 0.33894(6) 0.0497(2) Uani 1 2 d S T P . .
I3 I -0.01806(7) 0.250000 0.26057(5) 0.0430(2) Uani 1 2 d S T P . .
I4 I 0.25241(9) 0.250000 0.18436(7) 0.0775(3) Uani 1 2 d S T P . .
Cl1 Cl 0.6619(2) 0.0971(4) -0.0233(2) 0.1164(14) Uani 1 1 d . . . . .
C9 C 0.5847(15) 0.250000 0.0228(13) 0.134(4) Uani 1 2 d S T P . .
H9A H 0.485278 0.250000 -0.000017 0.161 Uiso 1 2 calc R U P . .
H9B H 0.593847 0.250001 0.099478 0.161 Uiso 1 2 calc R U P . .


_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 N3 2.242(8) . ?
I1 N1 2.264(7) . ?
N1 C1 1.344(7) 4_575 ?
N1 C1 1.344(7) . ?
N2 C3 1.362(11) . ?
N2 C4 1.463(7) . ?
N2 C4 1.463(7) 4_575 ?
N3 C5 1.344(8) . ?
N3 C5 1.344(8) 4_575 ?
N4 C7 1.337(11) . ?
N4 C8 1.461(8) 4_575 ?
N4 C8 1.461(8) . ?
C1 C2 1.358(9) . ?
C1 H1 0.9500 . ?
C2 C3 1.409(8) . ?
C2 H2 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.363(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.420(8) . ?
C6 H6 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
I2 I3 2.9532(10) . ?
I3 I4 2.8869(11) . ?
Cl1 C9 1.790(10) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 I1 N1 179.8(3) . . ?
C1 N1 C1 118.6(8) 4_575 . ?
C1 N1 I1 120.7(4) 4_575 . ?
C1 N1 I1 120.7(4) . . ?
C3 N2 C4 120.9(4) . . ?
C3 N2 C4 120.9(4) . 4_575 ?
C4 N2 C4 117.0(7) . 4_575 ?
C5 N3 C5 118.4(8) . 4_575 ?
C5 N3 I1 120.8(4) . . ?
C5 N3 I1 120.8(4) 4_575 . ?
C7 N4 C8 121.5(4) . 4_575 ?
C7 N4 C8 121.5(4) . . ?
C8 N4 C8 116.6(7) 4_575 . ?
N1 C1 C2 122.6(6) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C1 C2 C3 119.7(6) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
N2 C3 C2 121.6(4) . . ?
N2 C3 C2 121.6(4) . 4_575 ?
C2 C3 C2 116.7(8) . 4_575 ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N3 C5 C6 122.4(7) . . ?
N3 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C5 C6 C7 121.2(6) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
N4 C7 C6 122.8(4) . . ?
N4 C7 C6 122.8(4) . 4_575 ?
C6 C7 C6 114.4(8) . 4_575 ?
N4 C8 H8A 109.5 . . ?
N4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
I4 I3 I2 179.89(3) . . ?
Cl1 C9 Cl1 112.4(9) 4_565 . ?
Cl1 C9 H9A 109.1 4_565 . ?
Cl1 C9 H9A 109.1 . . ?
Cl1 C9 H9B 109.1 4_565 . ?
Cl1 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?

_refine_diff_density_max         1.468
_refine_diff_density_min         -1.190
_refine_diff_density_rms         0.162



####################################################################### 
# 
# 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_PPYH_I
_database_code_depnum_ccdc_archive 'CCDC 2255961'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        OID-040-2a
_chemical_name_common            
(NISac+4-Morpholinopyridine)+4-Pyrrolidinopyridine
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H13 N2, I'
_chemical_formula_sum            'C9 H13 I N2'
_chemical_formula_weight         276.11

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'
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                   7.3437(3)
_cell_length_b                   15.2166(6)
_cell_length_c                   18.5687(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.139(2)
_cell_angle_gamma                90
_cell_volume                     2066.64(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2571
_cell_measurement_theta_min      2.5800
_cell_measurement_theta_max      26.2340

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.775
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    3.051
_shelx_estimated_absorpt_T_min   0.354
_shelx_estimated_absorpt_T_max   0.693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97936
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.886
_oxdiff_exptl_absorpt_empirical_full_max 1.108
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8273
_diffrn_reflns_av_unetI/netI     0.0877
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.785
_diffrn_reflns_theta_max         26.244
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4148
_reflns_number_gt                3017
_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       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_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)+(0.0197P)²] 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         4148
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.0918
_refine_ls_wR_factor_gt          0.0771
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.55921(6) 0.55223(3) 0.89373(2) 0.02747(14) Uani 1 1 d . . . . .
N1 N 0.4090(6) 0.6873(4) 0.7469(3) 0.0259(14) Uani 1 1 d . . . . .
H1N H 0.458403 0.673692 0.795257 0.031 Uiso 1 1 calc R U . . .
N2 N 0.2097(7) 0.7463(4) 0.5384(3) 0.0273(14) Uani 1 1 d . . . . .
C1 C 0.3640(8) 0.7700(5) 0.7294(3) 0.0271(17) Uani 1 1 d . . . . .
H1 H 0.381179 0.814689 0.765119 0.032 Uiso 1 1 calc R U . . .
C2 C 0.2940(7) 0.7917(5) 0.6613(3) 0.0223(15) Uani 1 1 d . . . . .
H2 H 0.260489 0.850758 0.650271 0.027 Uiso 1 1 calc R U . . .
C3 C 0.2711(7) 0.7262(5) 0.6069(3) 0.0192(15) Uani 1 1 d . . . . .
C4 C 0.3172(8) 0.6388(5) 0.6283(3) 0.0269(17) Uani 1 1 d . . . . .
H4 H 0.300348 0.591755 0.594719 0.032 Uiso 1 1 calc R U . . .
C5 C 0.3859(8) 0.6233(5) 0.6979(3) 0.0292(18) Uani 1 1 d . . . . .
H5 H 0.418467 0.564916 0.711890 0.035 Uiso 1 1 calc R U . . .
C6 C 0.2002(9) 0.6830(5) 0.4789(3) 0.0352(19) Uani 1 1 d . . . . .
H6A H 0.092246 0.644161 0.480152 0.042 Uiso 1 1 calc R U . . .
H6B H 0.311947 0.646359 0.480844 0.042 Uiso 1 1 calc R U . . .
C7 C 0.1834(9) 0.7425(6) 0.4103(3) 0.044(2) Uani 1 1 d . . . . .
H7A H 0.305443 0.757630 0.395145 0.053 Uiso 1 1 calc R U . . .
H7B H 0.110993 0.713192 0.369581 0.053 Uiso 1 1 calc R U . . .
C8 C 0.0866(9) 0.8229(6) 0.4347(3) 0.043(2) Uani 1 1 d . . . . .
H8A H -0.047459 0.813937 0.429921 0.051 Uiso 1 1 calc R U . . .
H8B H 0.115646 0.874793 0.405659 0.051 Uiso 1 1 calc R U . . .
C9 C 0.1581(9) 0.8356(5) 0.5147(4) 0.038(2) Uani 1 1 d . . . . .
H9A H 0.264935 0.875535 0.519427 0.045 Uiso 1 1 calc R U . . .
H9B H 0.061530 0.859591 0.543088 0.045 Uiso 1 1 calc R U . . .
I2 I 0.68100(6) 0.88519(4) 0.87090(2) 0.03300(15) Uani 1 1 d . . . . .
N3 N 0.6765(7) 0.8486(4) 0.5701(3) 0.0284(14) Uani 1 1 d . . . . .
H3N H 0.633257 0.900575 0.544620 0.034 Uiso 1 1 calc R U . . .
N4 N 0.8531(7) 0.6248(4) 0.6783(3) 0.0228(13) Uani 1 1 d . . . . .
C10 C 0.7309(8) 0.8531(5) 0.6418(4) 0.0283(17) Uani 1 1 d . . . . .
H10 H 0.723033 0.907239 0.666757 0.034 Uiso 1 1 calc R U . . .
C11 C 0.7969(7) 0.7803(5) 0.6781(3) 0.0214(15) Uani 1 1 d . . . . .
H11 H 0.841745 0.785147 0.727528 0.026 Uiso 1 1 calc R U . . .
C12 C 0.7995(7) 0.6977(5) 0.6433(3) 0.0204(15) Uani 1 1 d . . . . .
C13 C 0.7423(7) 0.6977(5) 0.5677(3) 0.0229(16) Uani 1 1 d . . . . .
H13 H 0.746518 0.644794 0.540665 0.027 Uiso 1 1 calc R U . . .
C14 C 0.6827(8) 0.7722(5) 0.5346(4) 0.0288(18) Uani 1 1 d . . . . .
H14 H 0.643667 0.770617 0.484400 0.035 Uiso 1 1 calc R U . . .
C15 C 0.9199(8) 0.6244(5) 0.7555(3) 0.0299(18) Uani 1 1 d . . . . .
H15A H 0.821942 0.641676 0.785939 0.036 Uiso 1 1 calc R U . . .
H15B H 1.024960 0.664763 0.765097 0.036 Uiso 1 1 calc R U . . .
C16 C 0.9769(9) 0.5303(5) 0.7694(3) 0.0307(18) Uani 1 1 d . . . . .
H16A H 0.957916 0.512966 0.819595 0.037 Uiso 1 1 calc R U . . .
H16B H 1.107338 0.521917 0.761632 0.037 Uiso 1 1 calc R U . . .
C17 C 0.8556(8) 0.4767(5) 0.7156(4) 0.0339(18) Uani 1 1 d . . . . .
H17A H 0.734170 0.466172 0.733203 0.041 Uiso 1 1 calc R U . . .
H17B H 0.912624 0.419573 0.705571 0.041 Uiso 1 1 calc R U . . .
C18 C 0.8404(9) 0.5366(5) 0.6475(4) 0.0315(18) Uani 1 1 d . . . . .
H18A H 0.941558 0.525155 0.616931 0.038 Uiso 1 1 calc R U . . .
H18B H 0.722317 0.527749 0.618343 0.038 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
N1 C5 1.333(9) . ?
N1 C1 1.335(9) . ?
N1 H1N 0.9600 . ?
N2 C3 1.347(7) . ?
N2 C6 1.463(8) . ?
N2 C9 1.467(9) . ?
C1 C2 1.361(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.419(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.420(9) . ?
C4 C5 1.365(8) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.560(10) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.506(11) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.543(8) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N3 C14 1.340(9) . ?
N3 C10 1.357(8) . ?
N3 H3N 0.9600 . ?
N4 C12 1.327(8) . ?
N4 C18 1.458(9) . ?
N4 C15 1.473(7) . ?
C10 C11 1.363(9) . ?
C10 H10 0.9500 . ?
C11 C12 1.414(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.430(8) . ?
C13 C14 1.345(9) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.507(10) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.515(9) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.554(9) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C1 120.6(6) . . ?
C5 N1 H1N 119.7 . . ?
C1 N1 H1N 119.7 . . ?
C3 N2 C6 123.5(6) . . ?
C3 N2 C9 123.3(6) . . ?
C6 N2 C9 113.0(5) . . ?
N1 C1 C2 121.3(7) . . ?
N1 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C1 C2 C3 120.2(7) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
N2 C3 C2 121.4(6) . . ?
N2 C3 C4 121.9(6) . . ?
C2 C3 C4 116.6(6) . . ?
C5 C4 C3 119.0(7) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
N1 C5 C4 122.3(7) . . ?
N1 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
N2 C6 C7 103.2(6) . . ?
N2 C6 H6A 111.1 . . ?
C7 C6 H6A 111.1 . . ?
N2 C6 H6B 111.1 . . ?
C7 C6 H6B 111.1 . . ?
H6A C6 H6B 109.1 . . ?
C8 C7 C6 103.3(5) . . ?
C8 C7 H7A 111.1 . . ?
C6 C7 H7A 111.1 . . ?
C8 C7 H7B 111.1 . . ?
C6 C7 H7B 111.1 . . ?
H7A C7 H7B 109.1 . . ?
C7 C8 C9 105.2(6) . . ?
C7 C8 H8A 110.7 . . ?
C9 C8 H8A 110.7 . . ?
C7 C8 H8B 110.7 . . ?
C9 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?
N2 C9 C8 103.2(6) . . ?
N2 C9 H9A 111.1 . . ?
C8 C9 H9A 111.1 . . ?
N2 C9 H9B 111.1 . . ?
C8 C9 H9B 111.1 . . ?
H9A C9 H9B 109.1 . . ?
C14 N3 C10 120.4(6) . . ?
C14 N3 H3N 119.8 . . ?
C10 N3 H3N 119.8 . . ?
C12 N4 C18 124.9(5) . . ?
C12 N4 C15 122.5(6) . . ?
C18 N4 C15 112.4(6) . . ?
N3 C10 C11 120.4(7) . . ?
N3 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 121.0(6) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
N4 C12 C11 122.4(6) . . ?
N4 C12 C13 121.9(7) . . ?
C11 C12 C13 115.7(6) . . ?
C14 C13 C12 120.3(7) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
N3 C14 C13 122.1(6) . . ?
N3 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?
N4 C15 C16 103.5(6) . . ?
N4 C15 H15A 111.1 . . ?
C16 C15 H15A 111.1 . . ?
N4 C15 H15B 111.1 . . ?
C16 C15 H15B 111.1 . . ?
H15A C15 H15B 109.0 . . ?
C15 C16 C17 105.1(5) . . ?
C15 C16 H16A 110.7 . . ?
C17 C16 H16A 110.7 . . ?
C15 C16 H16B 110.7 . . ?
C17 C16 H16B 110.7 . . ?
H16A C16 H16B 108.8 . . ?
C16 C17 C18 102.5(6) . . ?
C16 C17 H17A 111.3 . . ?
C18 C17 H17A 111.3 . . ?
C16 C17 H17B 111.3 . . ?
C18 C17 H17B 111.3 . . ?
H17A C17 H17B 109.2 . . ?
N4 C18 C17 102.9(5) . . ?
N4 C18 H18A 111.2 . . ?
C17 C18 H18A 111.2 . . ?
N4 C18 H18B 111.2 . . ?
C17 C18 H18B 111.2 . . ?
H18A C18 H18B 109.1 . . ?

_refine_diff_density_max         1.402
_refine_diff_density_min         -1.053
_refine_diff_density_rms         0.167



####################################################################### 
# 
# 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_PPYH_NSac_2
_database_code_depnum_ccdc_archive 'CCDC 2255963'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        OID-041-2a
_chemical_name_common            
(NISac+4-Pyrrolidinopyridine)+4-Pyrrolidinopyridine
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 N O3 S, C9 H13 N2'
_chemical_formula_sum            'C16 H17 N3 O3 S'
_chemical_formula_weight         331.38

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'
S S 0.3331 0.5567 '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                   8.0985(3)
_cell_length_b                   8.1635(3)
_cell_length_c                   23.2286(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.541(3)
_cell_angle_gamma                90
_cell_volume                     1532.76(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4978
_cell_measurement_theta_min      3.7820
_cell_measurement_theta_max      75.6200

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    2.049
_shelx_estimated_absorpt_T_min   0.722
_shelx_estimated_absorpt_T_max   0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.88014
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.818
_oxdiff_exptl_absorpt_empirical_full_max 1.445
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2886
_diffrn_reflns_av_unetI/netI     0.1187
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.813
_diffrn_reflns_theta_max         69.979
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2886
_reflns_number_gt                2103
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0327P)²+4.1235P] 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         2886
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0866
_refine_ls_wR_factor_ref         0.2148
_refine_ls_wR_factor_gt          0.2077
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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
N1 N 0.2378(6) 0.4481(6) 0.5436(2) 0.0299(11) Uani 1 1 d . . . . .
H1N H 0.207867 0.547384 0.523461 0.036 Uiso 1 1 calc R U . . .
N2 N 0.3675(6) 0.0240(6) 0.6303(2) 0.0238(10) Uani 1 1 d . . . . .
C1 C 0.3522(8) 0.1819(8) 0.5430(3) 0.0327(14) Uani 1 1 d . . . . .
H1 H 0.398669 0.095168 0.522093 0.039 Uiso 1 1 calc R U . . .
C2 C 0.3098(10) 0.3245(8) 0.5158(3) 0.0402(16) Uani 1 1 d . . . . .
H2 H 0.331337 0.337489 0.476302 0.048 Uiso 1 1 calc R U . . .
C3 C 0.2079(8) 0.4316(7) 0.6001(3) 0.0296(13) Uani 1 1 d . . . . .
H3 H 0.153530 0.517578 0.618947 0.035 Uiso 1 1 calc R U . . .
C4 C 0.2536(7) 0.2958(7) 0.6301(2) 0.0257(12) Uani 1 1 d . . . . .
H4 H 0.236092 0.289672 0.670134 0.031 Uiso 1 1 calc R U . . .
C5 C 0.3276(7) 0.1620(7) 0.6024(2) 0.0244(12) Uani 1 1 d . . . . .
C6 C 0.4420(8) -0.1180(7) 0.6029(3) 0.0307(13) Uani 1 1 d . . . . .
H6A H 0.544363 -0.086401 0.584536 0.037 Uiso 1 1 calc R U . . .
H6B H 0.363710 -0.167565 0.573492 0.037 Uiso 1 1 calc R U . . .
C7 C 0.4800(8) -0.2363(8) 0.6532(3) 0.0366(15) Uani 1 1 d . . . . .
H7A H 0.464976 -0.351350 0.640533 0.044 Uiso 1 1 calc R U . . .
H7B H 0.594983 -0.221708 0.669514 0.044 Uiso 1 1 calc R U . . .
C8 C 0.3577(8) -0.1920(8) 0.6970(3) 0.0337(14) Uani 1 1 d . . . . .
H8A H 0.399703 -0.223087 0.736457 0.040 Uiso 1 1 calc R U . . .
H8B H 0.249806 -0.246127 0.688132 0.040 Uiso 1 1 calc R U . . .
C9 C 0.3427(8) -0.0060(7) 0.6910(3) 0.0308(13) Uani 1 1 d . . . . .
H9A H 0.232163 0.032088 0.701158 0.037 Uiso 1 1 calc R U . . .
H9B H 0.428325 0.050254 0.716073 0.037 Uiso 1 1 calc R U . . .
S1 S 0.21853(17) 0.63479(16) 0.34459(6) 0.0218(3) Uani 1 1 d . . . . .
O1 O 0.0952(5) 0.5397(5) 0.31161(17) 0.0281(9) Uani 1 1 d . . . . .
O2 O 0.3853(5) 0.6222(5) 0.32603(18) 0.0291(9) Uani 1 1 d . . . . .
O3 O 0.1490(6) 0.7364(5) 0.49442(17) 0.0334(10) Uani 1 1 d . . . . .
N3 N 0.2125(7) 0.5976(6) 0.4131(2) 0.0299(11) Uani 1 1 d . . . . .
C10 C 0.1586(7) 0.8435(7) 0.3467(2) 0.0246(12) Uani 1 1 d . . . . .
C11 C 0.1409(7) 0.9590(7) 0.3029(3) 0.0268(12) Uani 1 1 d . . . . .
H11 H 0.158922 0.932212 0.264022 0.032 Uiso 1 1 calc R U . . .
C12 C 0.0954(8) 1.1161(7) 0.3190(3) 0.0306(13) Uani 1 1 d . . . . .
H12 H 0.081767 1.199162 0.290453 0.037 Uiso 1 1 calc R U . . .
C13 C 0.0696(7) 1.1532(7) 0.3763(3) 0.0298(13) Uani 1 1 d . . . . .
H13 H 0.039823 1.261839 0.386022 0.036 Uiso 1 1 calc R U . . .
C14 C 0.0862(7) 1.0362(7) 0.4194(3) 0.0259(12) Uani 1 1 d . . . . .
H14 H 0.065439 1.061684 0.458193 0.031 Uiso 1 1 calc R U . . .
C15 C 0.1346(7) 0.8792(7) 0.4035(2) 0.0241(11) Uani 1 1 d . . . . .
C16 C 0.1634(7) 0.7315(7) 0.4415(2) 0.0248(12) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.350(8) . ?
N1 C3 1.355(8) . ?
N1 H1N 0.9600 . ?
N2 C5 1.330(7) . ?
N2 C9 1.458(8) . ?
N2 C6 1.469(7) . ?
C1 C2 1.358(9) . ?
C1 C5 1.414(8) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C4 1.349(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.420(8) . ?
C4 H4 0.9500 . ?
C6 C7 1.533(8) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.507(9) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.529(8) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
S1 O2 1.446(4) . ?
S1 O1 1.446(4) . ?
S1 N3 1.624(5) . ?
S1 C10 1.773(5) . ?
O3 C16 1.242(7) . ?
N3 C16 1.350(7) . ?
C10 C15 1.377(8) . ?
C10 C11 1.387(8) . ?
C11 C12 1.391(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(9) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.397(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.505(8) . ?

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
C2 N1 C3 119.9(5) . . ?
C2 N1 H1N 120.1 . . ?
C3 N1 H1N 120.1 . . ?
C5 N2 C9 124.8(5) . . ?
C5 N2 C6 123.4(5) . . ?
C9 N2 C6 111.8(5) . . ?
C2 C1 C5 120.4(6) . . ?
C2 C1 H1 119.8 . . ?
C5 C1 H1 119.8 . . ?
N1 C2 C1 121.4(6) . . ?
N1 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C4 C3 N1 121.5(6) . . ?
C4 C3 H3 119.3 . . ?
N1 C3 H3 119.3 . . ?
C3 C4 C5 120.5(5) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
N2 C5 C1 121.9(5) . . ?
N2 C5 C4 121.8(5) . . ?
C1 C5 C4 116.3(5) . . ?
N2 C6 C7 103.6(5) . . ?
N2 C6 H6A 111.0 . . ?
C7 C6 H6A 111.0 . . ?
N2 C6 H6B 111.0 . . ?
C7 C6 H6B 111.0 . . ?
H6A C6 H6B 109.0 . . ?
C8 C7 C6 104.7(5) . . ?
C8 C7 H7A 110.8 . . ?
C6 C7 H7A 110.8 . . ?
C8 C7 H7B 110.8 . . ?
C6 C7 H7B 110.8 . . ?
H7A C7 H7B 108.9 . . ?
C7 C8 C9 103.2(5) . . ?
C7 C8 H8A 111.1 . . ?
C9 C8 H8A 111.1 . . ?
C7 C8 H8B 111.1 . . ?
C9 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
N2 C9 C8 103.9(5) . . ?
N2 C9 H9A 111.0 . . ?
C8 C9 H9A 111.0 . . ?
N2 C9 H9B 111.0 . . ?
C8 C9 H9B 111.0 . . ?
H9A C9 H9B 109.0 . . ?
O2 S1 O1 115.5(3) . . ?
O2 S1 N3 111.3(3) . . ?
O1 S1 N3 110.9(3) . . ?
O2 S1 C10 109.8(3) . . ?
O1 S1 C10 110.4(3) . . ?
N3 S1 C10 97.4(3) . . ?
C16 N3 S1 110.8(4) . . ?
C15 C10 C11 123.0(5) . . ?
C15 C10 S1 106.5(4) . . ?
C11 C10 S1 130.5(5) . . ?
C10 C11 C12 116.6(5) . . ?
C10 C11 H11 121.7 . . ?
C12 C11 H11 121.7 . . ?
C11 C12 C13 121.0(5) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 121.8(5) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C15 117.3(5) . . ?
C13 C14 H14 121.4 . . ?
C15 C14 H14 121.4 . . ?
C10 C15 C14 120.4(5) . . ?
C10 C15 C16 111.6(5) . . ?
C14 C15 C16 128.0(5) . . ?
O3 C16 N3 124.0(5) . . ?
O3 C16 C15 122.3(5) . . ?
N3 C16 C15 113.7(5) . . ?

_refine_diff_density_max         0.793
_refine_diff_density_min         -0.703
_refine_diff_density_rms         0.101



