# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_psi371_n2n6
_database_code_depnum_ccdc_archive 'CCDC 2127474'
loop_
_audit_author_name
_audit_author_address
'Magali Allain'
;UNIV Angers, UMR CNRS
France
;
_audit_update_record             
;
2021-12-09 deposited with the CCDC.	2022-02-17 downloaded from the CCDC.
;

_audit_creation_date             2019-10-16T16:28:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         '2(C8 H11 I N4 O5), 2(H2 O)'
_chemical_formula_sum            'C16 H26 I2 N8 O12'
_chemical_formula_weight         776.25
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.1449(9)
_cell_length_b                   15.429(3)
_cell_length_c                   11.890(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.952(15)
_cell_angle_gamma                90
_cell_volume                     1291.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    1813
_cell_measurement_theta_min      4.653
_cell_measurement_theta_max      70.968

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.072
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.016
_exptl_crystal_density_diffrn    1.997
_exptl_crystal_F_000             760

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    19.813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.51707
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_detector_area_resol_mean 5.199
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_av_unetI/netI     0.1071
_diffrn_reflns_number            6796
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.774
_diffrn_reflns_theta_max         73.497
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.941
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 0.872
_diffrn_reflns_point_group_measured_fraction_max 0.828
_reflns_Friedel_fraction_full    0.761
_reflns_Friedel_fraction_max     0.706
_reflns_Friedel_coverage         0.694
_reflns_number_total             4304
_reflns_number_gt                2910
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 3.2k (Crystal Impact GbR, 2014)'
_computing_publication_material  'WinGX publication routines (Farrugia, V2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0689P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4304
_refine_ls_number_parameters     349
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0641
_refine_ls_wR_factor_ref         0.1763
_refine_ls_wR_factor_gt          0.1486
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_diff_density_max         0.925
_refine_diff_density_min         -1.336
_refine_diff_density_rms         0.123

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
N N 0.0311 0.018 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.325(3) 0.5673(16) 0.6057(17) 0.055(4) Uani 1 1 d . . . . .
C2 C 0.452(3) 0.5254(14) 0.5487(17) 0.052(4) Uani 1 1 d . . . . .
C3 C 0.425(3) 0.4592(14) 0.4583(17) 0.054(5) Uani 1 1 d . . . . .
C4 C 0.612(3) 0.4340(14) 0.4203(16) 0.048(4) Uani 1 1 d . . . . .
H4 H 0.703108 0.482108 0.428545 0.057 Uiso 1 1 calc R U . . .
C5 C 0.677(3) 0.3604(16) 0.503(2) 0.063(6) Uani 1 1 d . . . . .
H5 H 0.7214 0.384211 0.57963 0.076 Uiso 1 1 calc R U . . .
C6 C 0.488(4) 0.3149(18) 0.501(2) 0.061(5) Uani 1 1 d . . . . .
H6 H 0.458232 0.282942 0.428546 0.073 Uiso 1 1 calc R U . . .
C7 C 0.479(4) 0.2513(17) 0.598(2) 0.075(7) Uani 1 1 d . . . . .
H7A H 0.367467 0.214806 0.577917 0.09 Uiso 1 1 calc R U . . .
H7B H 0.590194 0.214252 0.607677 0.09 Uiso 1 1 calc R U . . .
C8 C 0.283(3) 0.4931(14) 0.3583(15) 0.053(5) Uani 1 1 d . . . . .
C9 C 0.644(3) 0.4693(18) -0.0993(19) 0.062(5) Uani 1 1 d . . . . .
C10 C 0.806(3) 0.5161(15) -0.0515(17) 0.054(5) Uani 1 1 d . . . . .
C11 C 0.816(3) 0.5923(14) 0.0311(18) 0.053(5) Uani 1 1 d . . . . .
C12 C 1.028(3) 0.6169(17) 0.0787(18) 0.061(5) Uani 1 1 d . . . . .
H12 H 1.113299 0.567011 0.079872 0.073 Uiso 1 1 calc R U . . .
C13 C 1.063(3) 0.6849(16) -0.0096(19) 0.059(5) Uani 1 1 d . . . . .
H13 H 1.072863 0.655246 -0.081256 0.071 Uiso 1 1 calc R U . . .
C14 C 0.875(3) 0.7362(17) -0.026(2) 0.062(5) Uani 1 1 d . . . . .
H14 H 0.872586 0.773853 0.040128 0.074 Uiso 1 1 calc R U . . .
C15 C 0.833(4) 0.7876(18) -0.1322(19) 0.069(6) Uani 1 1 d . . . . .
H15A H 0.700004 0.804244 -0.143846 0.083 Uiso 1 1 calc R U . . .
H15B H 0.907531 0.840421 -0.121644 0.083 Uiso 1 1 calc R U . . .
C16 C 0.721(3) 0.5679(18) 0.1309(15) 0.058(5) Uani 1 1 d . . . . .
I1 I 0.03162(19) 0.56076(11) 0.59232(14) 0.0736(5) Uani 1 1 d . . . . .
I2 I 0.36147(18) 0.47619(11) -0.08441(13) 0.0710(5) Uani 1 1 d . . . . .
N1 N 0.625(2) 0.5589(16) 0.5944(14) 0.061(5) Uani 1 1 d . . . . .
N2 N 0.607(3) 0.6168(14) 0.6720(15) 0.063(5) Uani 1 1 d . . . . .
H2 H 0.698456 0.645856 0.711052 0.076 Uiso 1 1 calc R U . . .
N3 N 0.423(3) 0.6236(13) 0.6809(17) 0.060(5) Uani 1 1 d . . . . .
N4 N 0.122(3) 0.4476(13) 0.3277(16) 0.064(5) Uani 1 1 d . . . . .
H4A H 0.035879 0.466026 0.273573 0.077 Uiso 1 1 calc R U . . .
H4B H 0.10594 0.399926 0.362202 0.077 Uiso 1 1 calc R U . . .
N5 N 0.709(3) 0.4125(14) -0.1660(17) 0.064(5) Uani 1 1 d . . . . .
N6 N 0.894(3) 0.4214(14) -0.1610(18) 0.071(6) Uani 1 1 d . . . . .
H6A H 0.963531 0.39101 -0.198336 0.085 Uiso 1 1 calc R U . . .
N7 N 0.954(2) 0.4845(16) -0.0895(15) 0.063(5) Uani 1 1 d . . . . .
N8 N 0.582(3) 0.6202(14) 0.1532(17) 0.070(5) Uani 1 1 d . . . . .
H8A H 0.523101 0.608457 0.208832 0.084 Uiso 1 1 calc R U . . .
H8B H 0.550724 0.665481 0.111939 0.084 Uiso 1 1 calc R U . . .
O1 O 0.351(2) 0.3807(10) 0.4992(14) 0.059(4) Uani 1 1 d . . . . .
O2 O 0.821(2) 0.3096(13) 0.4705(15) 0.078(5) Uani 1 1 d . . . . .
H2A H 0.918812 0.314845 0.517732 0.117 Uiso 1 1 calc R U . . .
O3 O 0.577(2) 0.4005(11) 0.3076(12) 0.060(4) Uani 1 1 d . . . . .
H3 H 0.593946 0.438784 0.262547 0.091 Uiso 1 1 calc R U . . .
O4 O 0.470(2) 0.2963(12) 0.7038(14) 0.069(4) Uani 1 1 d . . . . .
H4C H 0.55265 0.333885 0.714238 0.104 Uiso 1 1 calc R U . . .
O5 O 0.317(2) 0.5632(12) 0.3121(12) 0.065(4) Uani 1 1 d . . . . .
O6 O 0.7362(19) 0.6681(10) -0.0282(13) 0.060(4) Uani 1 1 d . . . . .
O7 O 1.043(2) 0.6561(12) 0.1883(12) 0.064(4) Uani 1 1 d . . . . .
H7 H 1.10988 0.625881 0.23594 0.096 Uiso 1 1 calc R U . . .
O8 O 1.229(3) 0.7340(12) 0.0250(16) 0.074(4) Uani 1 1 d . . . . .
H8 H 1.258397 0.758473 -0.030643 0.11 Uiso 1 1 calc R U . . .
O9 O 0.869(2) 0.7461(12) -0.2326(13) 0.067(4) Uani 1 1 d . . . . .
H9 H 0.977042 0.757192 -0.242033 0.101 Uiso 1 1 calc R U . . .
O10 O 0.770(2) 0.5032(10) 0.1863(12) 0.065(4) Uani 1 1 d . . . . .
O11 O 0.928(2) 0.8018(12) 0.3033(16) 0.075(4) Uani 1 1 d . . . . .
H11A H 0.909666 0.752283 0.272049 0.112 Uiso 1 1 d R U . . .
H11B H 0.816989 0.819303 0.309503 0.112 Uiso 1 1 d R U . . .
O12 O 0.265(2) 0.7564(11) 0.7898(15) 0.074(4) Uani 1 1 d . . . . .
H12A H 0.323215 0.71046 0.776771 0.11 Uiso 1 1 d R U . . .
H12B H 0.284653 0.791465 0.737882 0.11 Uiso 1 1 d R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N3 1.35(3) . ?
C1 C2 1.39(3) . ?
C1 I1 2.076(18) . ?
C2 N1 1.36(3) . ?
C2 C3 1.47(3) . ?
C3 O1 1.44(2) . ?
C3 C8 1.52(3) . ?
C3 C4 1.53(3) . ?
C4 O3 1.42(2) . ?
C4 C5 1.52(3) . ?
C4 H4 0.98 . ?
C5 O2 1.40(3) . ?
C5 C6 1.52(4) . ?
C5 H5 0.98 . ?
C6 O1 1.41(3) . ?
C6 C7 1.52(4) . ?
C6 H6 0.98 . ?
C7 O4 1.45(3) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 O5 1.26(3) . ?
C8 N4 1.34(3) . ?
C9 N5 1.32(3) . ?
C9 C10 1.40(3) . ?
C9 I2 2.057(18) . ?
C10 N7 1.31(3) . ?
C10 C11 1.53(3) . ?
C11 O6 1.43(2) . ?
C11 C16 1.51(3) . ?
C11 C12 1.57(3) . ?
C12 O7 1.42(3) . ?
C12 C13 1.53(3) . ?
C12 H12 0.98 . ?
C13 O8 1.41(3) . ?
C13 C14 1.54(3) . ?
C13 H13 0.98 . ?
C14 O6 1.44(3) . ?
C14 C15 1.48(3) . ?
C14 H14 0.98 . ?
C15 O9 1.42(3) . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C16 O10 1.21(3) . ?
C16 N8 1.34(3) . ?
N1 N2 1.31(3) . ?
N2 N3 1.34(3) . ?
N2 H2 0.86 . ?
N4 H4A 0.86 . ?
N4 H4B 0.86 . ?
N5 N6 1.32(3) . ?
N6 N7 1.31(3) . ?
N6 H6A 0.86 . ?
N8 H8A 0.86 . ?
N8 H8B 0.86 . ?
O2 H2A 0.82 . ?
O3 H3 0.82 . ?
O4 H4C 0.82 . ?
O7 H7 0.82 . ?
O8 H8 0.82 . ?
O9 H9 0.82 . ?
O11 H11A 0.8501 . ?
O11 H11B 0.8501 . ?
O12 H12A 0.8502 . ?
O12 H12B 0.8503 . ?

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 C1 C2 108.2(17) . . ?
N3 C1 I1 119.0(15) . . ?
C2 C1 I1 132.8(16) . . ?
N1 C2 C1 104.7(19) . . ?
N1 C2 C3 123.5(19) . . ?
C1 C2 C3 131.8(18) . . ?
O1 C3 C2 110.4(16) . . ?
O1 C3 C8 108.7(16) . . ?
C2 C3 C8 108.6(17) . . ?
O1 C3 C4 106.0(16) . . ?
C2 C3 C4 112.3(17) . . ?
C8 C3 C4 110.8(15) . . ?
O3 C4 C5 108.9(17) . . ?
O3 C4 C3 110.6(15) . . ?
C5 C4 C3 100.5(16) . . ?
O3 C4 H4 112.1 . . ?
C5 C4 H4 112.1 . . ?
C3 C4 H4 112.1 . . ?
O2 C5 C6 115(2) . . ?
O2 C5 C4 113.2(19) . . ?
C6 C5 C4 99.2(18) . . ?
O2 C5 H5 109.5 . . ?
C6 C5 H5 109.5 . . ?
C4 C5 H5 109.5 . . ?
O1 C6 C5 106(2) . . ?
O1 C6 C7 111(2) . . ?
C5 C6 C7 116(2) . . ?
O1 C6 H6 107.9 . . ?
C5 C6 H6 107.9 . . ?
C7 C6 H6 107.9 . . ?
O4 C7 C6 111(2) . . ?
O4 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
O4 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108 . . ?
O5 C8 N4 123.8(18) . . ?
O5 C8 C3 118.9(17) . . ?
N4 C8 C3 117.2(18) . . ?
N5 C9 C10 103.3(17) . . ?
N5 C9 I2 122.8(18) . . ?
C10 C9 I2 134.0(18) . . ?
N7 C10 C9 109(2) . . ?
N7 C10 C11 124(2) . . ?
C9 C10 C11 126.8(19) . . ?
O6 C11 C16 113.3(17) . . ?
O6 C11 C10 110.0(16) . . ?
C16 C11 C10 109.7(18) . . ?
O6 C11 C12 104.8(17) . . ?
C16 C11 C12 108.3(17) . . ?
C10 C11 C12 110.5(18) . . ?
O7 C12 C13 110(2) . . ?
O7 C12 C11 110.3(18) . . ?
C13 C12 C11 100.3(16) . . ?
O7 C12 H12 111.9 . . ?
C13 C12 H12 111.9 . . ?
C11 C12 H12 111.9 . . ?
O8 C13 C12 113.3(17) . . ?
O8 C13 C14 116(2) . . ?
C12 C13 C14 101.4(17) . . ?
O8 C13 H13 108.7 . . ?
C12 C13 H13 108.7 . . ?
C14 C13 H13 108.7 . . ?
O6 C14 C15 109.7(19) . . ?
O6 C14 C13 102.1(19) . . ?
C15 C14 C13 115(2) . . ?
O6 C14 H14 109.8 . . ?
C15 C14 H14 109.8 . . ?
C13 C14 H14 109.8 . . ?
O9 C15 C14 116(2) . . ?
O9 C15 H15A 108.3 . . ?
C14 C15 H15A 108.3 . . ?
O9 C15 H15B 108.3 . . ?
C14 C15 H15B 108.3 . . ?
H15A C15 H15B 107.4 . . ?
O10 C16 N8 122.8(19) . . ?
O10 C16 C11 120.2(19) . . ?
N8 C16 C11 117(2) . . ?
N2 N1 C2 110.6(18) . . ?
N1 N2 N3 109.0(17) . . ?
N1 N2 H2 125.5 . . ?
N3 N2 H2 125.5 . . ?
N2 N3 C1 107.6(17) . . ?
C8 N4 H4A 120 . . ?
C8 N4 H4B 120 . . ?
H4A N4 H4B 120 . . ?
N6 N5 C9 111.2(19) . . ?
N7 N6 N5 108.5(18) . . ?
N7 N6 H6A 125.7 . . ?
N5 N6 H6A 125.7 . . ?
C10 N7 N6 107.9(17) . . ?
C16 N8 H8A 120 . . ?
C16 N8 H8B 120 . . ?
H8A N8 H8B 120 . . ?
C6 O1 C3 108.6(16) . . ?
C5 O2 H2A 109.5 . . ?
C4 O3 H3 109.5 . . ?
C7 O4 H4C 109.5 . . ?
C11 O6 C14 111.9(15) . . ?
C12 O7 H7 109.5 . . ?
C13 O8 H8 109.5 . . ?
C15 O9 H9 109.5 . . ?
H11A O11 H11B 104.5 . . ?
H12A O12 H12B 104.5 . . ?

