# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_SUST_2453_0m
_database_code_depnum_ccdc_archive 'CCDC 1944954'
loop_
_audit_author_name
_audit_author_address
LL
;Northwest University
China
;
_audit_update_record             
;
2019-08-02 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 I N6 O2'
_chemical_formula_weight         501.30

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'

_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                   9.7382(14)
_cell_length_b                   10.0324(13)
_cell_length_c                   11.2964(15)
_cell_angle_alpha                73.551(7)
_cell_angle_beta                 87.711(7)
_cell_angle_gamma                74.719(7)
_cell_volume                     1020.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8643
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      28.36

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_F_000             498
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    1.598
_shelx_estimated_absorpt_T_min   0.796
_shelx_estimated_absorpt_T_max   0.819
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9970
_diffrn_reflns_av_unetI/netI     0.0831
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.453
_diffrn_reflns_theta_max         28.391
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5013
_reflns_number_gt                4456
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_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)+(0.0573P)²+0.2416P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5013
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1240
_refine_ls_wR_factor_gt          0.1191
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
C1 C 0.4366(4) 0.4561(4) 0.2425(3) 0.0218(7) Uani 1 1 d . . . . .
C2 C 0.5536(4) 0.4511(4) 0.3239(3) 0.0239(7) Uani 1 1 d . . . . .
C3 C 0.6215(4) 0.3198(4) 0.4067(4) 0.0342(9) Uani 1 1 d . . . . .
H3 H 0.5980 0.2335 0.4077 0.041 Uiso 1 1 calc R U . . .
C4 C 0.7242(5) 0.3201(6) 0.4873(4) 0.0497(13) Uani 1 1 d . . . . .
H4 H 0.7724 0.2328 0.5456 0.060 Uiso 1 1 calc R U . . .
C5 C 0.7571(5) 0.4469(7) 0.4833(4) 0.0459(12) Uani 1 1 d . . . . .
H5 H 0.8273 0.4479 0.5388 0.055 Uiso 1 1 calc R U . . .
C6 C 0.6868(5) 0.5712(6) 0.3980(4) 0.0404(10) Uani 1 1 d . . . . .
H6 H 0.7112 0.6578 0.3944 0.048 Uiso 1 1 calc R U . . .
C7 C 0.2820(4) 0.5217(4) 0.0890(3) 0.0213(6) Uani 1 1 d . . . . .
C8 C 0.2055(4) 0.5901(4) -0.0299(3) 0.0215(6) Uani 1 1 d . . . . .
C9 C 0.1404(4) 0.5147(4) -0.0857(3) 0.0254(7) Uani 1 1 d . . . . .
H9 H 0.1469 0.4158 -0.0473 0.031 Uiso 1 1 calc R U . . .
C10 C 0.0661(4) 0.5840(4) -0.1975(3) 0.0257(7) Uani 1 1 d . . . . .
H10 H 0.0218 0.5328 -0.2365 0.031 Uiso 1 1 calc R U . . .
C11 C 0.0566(4) 0.7301(4) -0.2530(4) 0.0287(8) Uani 1 1 d . . . . .
H11 H 0.0061 0.7790 -0.3298 0.034 Uiso 1 1 calc R U . . .
C12 C 0.1212(4) 0.8014(4) -0.1947(3) 0.0251(7) Uani 1 1 d . . . . .
H12 H 0.1149 0.9006 -0.2317 0.030 Uiso 1 1 calc R U . . .
C13 C 0.2556(3) 0.8163(3) -0.0221(3) 0.0207(6) Uani 1 1 d . . . . .
H13A H 0.2157 0.8080 0.0608 0.025 Uiso 1 1 calc R U . . .
H13B H 0.2279 0.9193 -0.0698 0.025 Uiso 1 1 calc R U . . .
C14 C 0.4164(3) 0.7640(4) -0.0090(3) 0.0190(6) Uani 1 1 d . . . . .
C15 C 0.5055(4) 0.8565(3) -0.0768(3) 0.0190(6) Uani 1 1 d . . . . .
C16 C 0.6406(4) 0.8418(4) -0.0250(3) 0.0210(6) Uani 1 1 d . . . . .
H16 H 0.6705 0.7759 0.0540 0.025 Uiso 1 1 calc R U . . .
C17 C 0.7284(4) 0.9222(4) -0.0885(3) 0.0253(7) Uani 1 1 d . . . . .
H17 H 0.8199 0.9099 -0.0541 0.030 Uiso 1 1 calc R U . . .
C18 C 0.6842(4) 1.0222(4) -0.2032(3) 0.0283(8) Uani 1 1 d . . . . .
H18 H 0.7457 1.0770 -0.2469 0.034 Uiso 1 1 calc R U . . .
C19 C 0.5493(4) 1.0413(4) -0.2534(3) 0.0287(8) Uani 1 1 d . . . . .
H19 H 0.5180 1.1108 -0.3305 0.034 Uiso 1 1 calc R U . . .
C20 C 0.4610(4) 0.9584(4) -0.1905(3) 0.0249(7) Uani 1 1 d . . . . .
H20 H 0.3696 0.9711 -0.2251 0.030 Uiso 1 1 calc R U . . .
I1 I 1.02272(2) 0.21535(2) 0.78279(2) 0.02595(10) Uani 1 1 d . . . . .
N1 N 0.2546(3) 0.4086(3) 0.1702(3) 0.0249(6) Uani 1 1 d . . . . .
N2 N 0.3522(3) 0.3678(3) 0.2686(3) 0.0255(6) Uani 1 1 d . . . . .
N3 N 0.3954(3) 0.5559(3) 0.1304(3) 0.0206(6) Uani 1 1 d . . . . .
N4 N 0.4819(3) 0.6412(3) 0.0641(3) 0.0200(5) Uani 1 1 d . . . . .
N5 N 0.1940(3) 0.7328(3) -0.0854(3) 0.0203(6) Uani 1 1 d . . . . .
N6 N 0.5833(4) 0.5762(4) 0.3179(3) 0.0341(7) Uani 1 1 d . . . . .
O1 O 0.1007(3) 0.0596(4) 0.5331(3) 0.0395(7) Uani 1 1 d . . . . .
O2 O 0.3684(3) 0.1085(3) 0.4826(3) 0.0345(6) Uani 1 1 d . . . . .
H1A H 0.0629 0.1159 0.5772 0.052 Uiso 1 1 d R U . . .
H2A H 0.3639 0.1823 0.4214 0.052 Uiso 1 1 d R U . . .
H2B H 0.2868 0.0935 0.4979 0.052 Uiso 1 1 d 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
C1 N2 1.327(5) . ?
C1 N3 1.370(4) . ?
C1 C2 1.474(5) . ?
C2 N6 1.343(5) . ?
C2 C3 1.393(5) . ?
C3 C4 1.381(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.370(7) . ?
C5 H5 0.9500 . ?
C6 N6 1.363(5) . ?
C6 H6 0.9500 . ?
C7 N1 1.323(5) . ?
C7 N3 1.374(4) . ?
C7 C8 1.456(5) . ?
C8 N5 1.367(4) . ?
C8 C9 1.388(5) . ?
C9 C10 1.383(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.401(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.371(5) . ?
C11 H11 0.9500 . ?
C12 N5 1.354(4) . ?
C12 H12 0.9500 . ?
C13 N5 1.487(4) . ?
C13 C14 1.514(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N4 1.288(4) . ?
C14 C15 1.473(5) . ?
C15 C20 1.396(5) . ?
C15 C16 1.415(5) . ?
C16 C17 1.373(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.397(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.396(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.389(5) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
N1 N2 1.388(4) . ?
N3 N4 1.402(4) . ?
O1 H1A 0.8591 . ?
O2 H2A 0.8501 . ?
O2 H2B 0.8500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N3 109.8(3) . . ?
N2 C1 C2 125.2(3) . . ?
N3 C1 C2 125.0(3) . . ?
N6 C2 C3 123.8(4) . . ?
N6 C2 C1 117.4(3) . . ?
C3 C2 C1 118.7(4) . . ?
C4 C3 C2 117.5(4) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C5 C4 C3 120.1(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C6 C5 C4 118.8(4) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
N6 C6 C5 123.0(5) . . ?
N6 C6 H6 118.5 . . ?
C5 C6 H6 118.5 . . ?
N1 C7 N3 110.5(3) . . ?
N1 C7 C8 122.7(3) . . ?
N3 C7 C8 126.7(3) . . ?
N5 C8 C9 119.6(3) . . ?
N5 C8 C7 119.0(3) . . ?
C9 C8 C7 121.4(3) . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 119.6(3) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 119.0(3) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
N5 C12 C11 121.0(3) . . ?
N5 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
N5 C13 C14 112.1(2) . . ?
N5 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
N5 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
N4 C14 C15 116.8(3) . . ?
N4 C14 C13 122.6(3) . . ?
C15 C14 C13 120.5(3) . . ?
C20 C15 C16 118.9(3) . . ?
C20 C15 C14 122.1(3) . . ?
C16 C15 C14 118.9(3) . . ?
C17 C16 C15 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.5(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 119.9(3) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C20 C19 C18 119.9(3) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C15 120.6(3) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?
C7 N1 N2 106.9(3) . . ?
C1 N2 N1 107.8(3) . . ?
C1 N3 C7 105.1(3) . . ?
C1 N3 N4 123.1(3) . . ?
C7 N3 N4 129.3(3) . . ?
C14 N4 N3 116.1(3) . . ?
C12 N5 C8 121.0(3) . . ?
C12 N5 C13 119.2(3) . . ?
C8 N5 C13 119.7(3) . . ?
C2 N6 C6 116.8(4) . . ?
H2A O2 H2B 111.2 . . ?

_refine_diff_density_max         0.954
_refine_diff_density_min         -1.347
_refine_diff_density_rms         0.194



####################################################################### 
# 
# 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_mo_20181103_lh_pt_0m
_database_code_depnum_ccdc_archive 'CCDC 1944955'
loop_
_audit_author_name
_audit_author_address
LL
;Northwest University
China
;
_audit_update_record             
;
2019-08-02 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;
_audit_creation_date             2018-11-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'I, C20 H14 Cl N6, C2 H6 O S'
_chemical_formula_sum            'C22 H20 Cl I N6 O S'
_chemical_formula_weight         578.85
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.6849(4)
_cell_length_b                   11.3310(5)
_cell_length_c                   14.1776(7)
_cell_angle_alpha                94.684(2)
_cell_angle_beta                 94.245(2)
_cell_angle_gamma                106.982(2)
_cell_volume                     1170.56(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    297.99
_cell_measurement_theta_max      25.332
_cell_measurement_theta_min      2.503
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.598
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0699 before and 0.0434 after correction. The Ratio of minimum to maximum transmission is 0.9254. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33753
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.393
_diffrn_reflns_theta_min         2.786
_diffrn_ambient_temperature      297.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3968
_reflns_number_total             4290
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0220
_refine_ls_R_factor_gt           0.0193
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0208P)²+0.3649P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0469
_refine_ls_wR_factor_ref         0.0481
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I -0.11890(2) 0.75286(2) 0.13373(2) 0.04766(6) Uani 1 1 d . . . . .
Cl1 Cl 0.16088(7) 0.48675(5) 0.42217(4) 0.05485(14) Uani 1 1 d . . . . .
N1 N 0.5671(2) 0.75221(13) 0.33116(11) 0.0358(3) Uani 1 1 d . . . . .
N2 N 0.5407(2) 0.85719(13) 0.29379(11) 0.0350(3) Uani 1 1 d . . . . .
N3 N 0.5076(2) 0.98807(14) 0.19198(13) 0.0447(4) Uani 1 1 d . . . . .
N4 N 0.6005(2) 1.05498(14) 0.27534(13) 0.0460(4) Uani 1 1 d . . . . .
N5 N 0.6717(2) 0.93840(15) 0.49786(12) 0.0444(4) Uani 1 1 d . . . . .
N6 N 0.3029(2) 0.65710(14) 0.14638(12) 0.0389(4) Uani 1 1 d . . . . .
C1 C 0.3570(3) 0.45543(17) 0.38802(14) 0.0394(4) Uani 1 1 d . . . . .
C2 C 0.4758(2) 0.53669(16) 0.33668(13) 0.0357(4) Uani 1 1 d . . . . .
C3 C 0.4396(2) 0.65029(16) 0.30661(14) 0.0352(4) Uani 1 1 d . . . . .
C4 C 0.4736(2) 0.86990(16) 0.20376(14) 0.0379(4) Uani 1 1 d . . . . .
C5 C 0.6229(2) 0.97662(16) 0.33522(14) 0.0379(4) Uani 1 1 d . . . . .
C6 C 0.7188(3) 1.01551(17) 0.43130(14) 0.0385(4) Uani 1 1 d . . . . .
C7 C 0.7591(3) 0.9784(2) 0.58477(16) 0.0524(5) Uani 1 1 d . . . . .
H7 H 0.728914 0.926511 0.632432 0.063 Uiso 1 1 calc R . . . .
C8 C 0.8905(3) 1.0911(2) 0.60864(17) 0.0572(6) Uani 1 1 d . . . . .
H8 H 0.947149 1.114068 0.670434 0.069 Uiso 1 1 calc R . . . .
C9 C 0.9361(3) 1.1688(2) 0.53900(18) 0.0583(6) Uani 1 1 d . . . . .
H9 H 1.023815 1.245897 0.552904 0.070 Uiso 1 1 calc R . . . .
C10 C 0.8499(3) 1.13082(19) 0.44832(16) 0.0488(5) Uani 1 1 d . . . . .
H10 H 0.878775 1.181239 0.399648 0.059 Uiso 1 1 calc R . . . .
C11 C 0.3965(2) 0.77217(16) 0.12624(14) 0.0380(4) Uani 1 1 d . . . . .
C12 C 0.2644(2) 0.63811(18) 0.24523(15) 0.0412(4) Uani 1 1 d . . . . .
H12A H 0.179119 0.556256 0.246896 0.049 Uiso 1 1 calc R . . . .
H12B H 0.208544 0.699149 0.269898 0.049 Uiso 1 1 calc R . . . .
C13 C 0.2354(3) 0.56253(19) 0.07599(18) 0.0522(5) Uani 1 1 d . . . . .
H13 H 0.174873 0.483592 0.091064 0.063 Uiso 1 1 calc R . . . .
C14 C 0.2555(3) 0.5821(2) -0.01654(18) 0.0603(6) Uani 1 1 d . . . . .
H14 H 0.210342 0.516556 -0.064404 0.072 Uiso 1 1 calc R . . . .
C15 C 0.3428(3) 0.6993(2) -0.03910(17) 0.0564(6) Uani 1 1 d . . . . .
H15 H 0.351560 0.714492 -0.102319 0.068 Uiso 1 1 calc R . . . .
C16 C 0.4169(3) 0.7937(2) 0.03320(15) 0.0478(5) Uani 1 1 d . . . . .
H16 H 0.481014 0.872318 0.018922 0.057 Uiso 1 1 calc R . . . .
C17 C 0.6326(3) 0.50921(18) 0.31182(15) 0.0429(5) Uani 1 1 d . . . . .
H17 H 0.714444 0.563079 0.278091 0.051 Uiso 1 1 calc R . . . .
C18 C 0.6675(3) 0.40197(19) 0.33705(17) 0.0510(5) Uani 1 1 d . . . . .
H18 H 0.770120 0.382422 0.318286 0.061 Uiso 1 1 calc R . . . .
C19 C 0.5496(3) 0.32443(19) 0.39005(17) 0.0538(6) Uani 1 1 d . . . . .
H19 H 0.574771 0.253642 0.408282 0.065 Uiso 1 1 calc R . . . .
C20 C 0.3951(3) 0.35076(18) 0.41622(16) 0.0483(5) Uani 1 1 d . . . . .
H20 H 0.316744 0.298633 0.452578 0.058 Uiso 1 1 calc R . . . .
S1 S 0.05677(9) 0.21442(6) 0.20039(4) 0.05631(15) Uani 1 1 d . . . . .
O1 O 0.0281(2) 0.33717(14) 0.18754(13) 0.0671(5) Uani 1 1 d . . . . .
C21 C -0.0836(4) 0.1072(2) 0.10683(19) 0.0676(7) Uani 1 1 d . . . . .
H21A H -0.209980 0.096242 0.115291 0.101 Uiso 1 1 calc GR . . . .
H21B H -0.059165 0.028936 0.107773 0.101 Uiso 1 1 calc GR . . . .
H21C H -0.057628 0.138604 0.046886 0.101 Uiso 1 1 calc GR . . . .
C22 C 0.2693(4) 0.2205(3) 0.1568(2) 0.0838(9) Uani 1 1 d . . . . .
H22A H 0.266655 0.240062 0.092227 0.126 Uiso 1 1 calc GR . . . .
H22B H 0.290720 0.141363 0.159297 0.126 Uiso 1 1 calc GR . . . .
H22C H 0.365725 0.283198 0.195360 0.126 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.739(2) . ?
N1 N2 1.402(2) . ?
N1 C3 1.280(2) . ?
N2 C4 1.376(2) . ?
N2 C5 1.375(2) . ?
N3 N4 1.376(2) . ?
N3 C4 1.314(2) . ?
N4 C5 1.315(3) . ?
N5 C6 1.336(3) . ?
N5 C7 1.335(3) . ?
N6 C11 1.358(2) . ?
N6 C12 1.474(3) . ?
N6 C13 1.355(3) . ?
C1 C2 1.388(3) . ?
C1 C20 1.384(3) . ?
C2 C3 1.482(2) . ?
C2 C17 1.392(3) . ?
C3 C12 1.513(3) . ?
C4 C11 1.451(3) . ?
C5 C6 1.468(3) . ?
C6 C10 1.387(3) . ?
C7 C8 1.375(3) . ?
C8 C9 1.374(3) . ?
C9 C10 1.376(3) . ?
C11 C16 1.373(3) . ?
C13 C14 1.361(3) . ?
C14 C15 1.377(3) . ?
C15 C16 1.378(3) . ?
C17 C18 1.387(3) . ?
C18 C19 1.379(3) . ?
C19 C20 1.375(3) . ?
S1 O1 1.4936(17) . ?
S1 C21 1.777(3) . ?
S1 C22 1.774(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 N2 115.72(15) . . ?
C4 N2 N1 129.67(15) . . ?
C5 N2 N1 123.58(15) . . ?
C5 N2 C4 104.92(15) . . ?
C4 N3 N4 107.18(16) . . ?
C5 N4 N3 108.47(15) . . ?
C7 N5 C6 116.00(18) . . ?
C11 N6 C12 119.03(16) . . ?
C13 N6 C11 120.70(18) . . ?
C13 N6 C12 120.13(17) . . ?
C2 C1 Cl1 120.35(14) . . ?
C20 C1 Cl1 118.58(16) . . ?
C20 C1 C2 121.03(19) . . ?
C1 C2 C3 122.17(17) . . ?
C1 C2 C17 118.61(17) . . ?
C17 C2 C3 119.21(17) . . ?
N1 C3 C2 116.06(16) . . ?
N1 C3 C12 124.77(16) . . ?
C2 C3 C12 119.06(15) . . ?
N2 C4 C11 127.18(16) . . ?
N3 C4 N2 110.11(16) . . ?
N3 C4 C11 122.28(18) . . ?
N2 C5 C6 127.24(17) . . ?
N4 C5 N2 109.26(17) . . ?
N4 C5 C6 123.49(17) . . ?
N5 C6 C5 117.86(17) . . ?
N5 C6 C10 123.77(19) . . ?
C10 C6 C5 118.35(19) . . ?
N5 C7 C8 124.5(2) . . ?
C9 C8 C7 118.4(2) . . ?
C8 C9 C10 119.0(2) . . ?
C9 C10 C6 118.4(2) . . ?
N6 C11 C4 119.19(18) . . ?
N6 C11 C16 119.45(18) . . ?
C16 C11 C4 121.36(17) . . ?
N6 C12 C3 110.12(15) . . ?
N6 C13 C14 120.6(2) . . ?
C13 C14 C15 119.8(2) . . ?
C14 C15 C16 119.1(2) . . ?
C11 C16 C15 120.2(2) . . ?
C18 C17 C2 120.41(19) . . ?
C19 C18 C17 119.8(2) . . ?
C20 C19 C18 120.65(19) . . ?
C19 C20 C1 119.5(2) . . ?
O1 S1 C21 106.48(12) . . ?
O1 S1 C22 105.97(14) . . ?
C22 S1 C21 96.71(14) . . ?

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
Cl1 C1 C2 C3 -1.7(3) . . . . ?
Cl1 C1 C2 C17 179.13(15) . . . . ?
Cl1 C1 C20 C19 -179.93(17) . . . . ?
N1 N2 C4 N3 -166.37(17) . . . . ?
N1 N2 C4 C11 6.2(3) . . . . ?
N1 N2 C5 N4 168.04(16) . . . . ?
N1 N2 C5 C6 -13.1(3) . . . . ?
N1 C3 C12 N6 70.8(2) . . . . ?
N2 N1 C3 C2 173.28(15) . . . . ?
N2 N1 C3 C12 -2.8(3) . . . . ?
N2 C4 C11 N6 32.6(3) . . . . ?
N2 C4 C11 C16 -147.2(2) . . . . ?
N2 C5 C6 N5 -26.0(3) . . . . ?
N2 C5 C6 C10 155.35(19) . . . . ?
N3 N4 C5 N2 -1.8(2) . . . . ?
N3 N4 C5 C6 179.28(17) . . . . ?
N3 C4 C11 N6 -155.60(18) . . . . ?
N3 C4 C11 C16 24.6(3) . . . . ?
N4 N3 C4 N2 0.6(2) . . . . ?
N4 N3 C4 C11 -172.42(17) . . . . ?
N4 C5 C6 N5 152.71(19) . . . . ?
N4 C5 C6 C10 -26.0(3) . . . . ?
N5 C6 C10 C9 -0.4(3) . . . . ?
N5 C7 C8 C9 0.2(4) . . . . ?
N6 C11 C16 C15 0.0(3) . . . . ?
N6 C13 C14 C15 -0.9(3) . . . . ?
C1 C2 C3 N1 125.7(2) . . . . ?
C1 C2 C3 C12 -58.0(3) . . . . ?
C1 C2 C17 C18 0.8(3) . . . . ?
C2 C1 C20 C19 -2.4(3) . . . . ?
C2 C3 C12 N6 -105.16(19) . . . . ?
C2 C17 C18 C19 -2.4(3) . . . . ?
C3 N1 N2 C4 -41.4(3) . . . . ?
C3 N1 N2 C5 156.44(17) . . . . ?
C3 C2 C17 C18 -178.44(18) . . . . ?
C4 N2 C5 N4 2.1(2) . . . . ?
C4 N2 C5 C6 -179.03(18) . . . . ?
C4 N3 N4 C5 0.8(2) . . . . ?
C4 C11 C16 C15 179.87(19) . . . . ?
C5 N2 C4 N3 -1.7(2) . . . . ?
C5 N2 C4 C11 170.92(18) . . . . ?
C5 C6 C10 C9 178.20(19) . . . . ?
C6 N5 C7 C8 0.0(3) . . . . ?
C7 N5 C6 C5 -178.50(17) . . . . ?
C7 N5 C6 C10 0.1(3) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C8 C9 C10 C6 0.6(3) . . . . ?
C11 N6 C12 C3 -69.3(2) . . . . ?
C11 N6 C13 C14 -2.0(3) . . . . ?
C12 N6 C11 C4 6.8(2) . . . . ?
C12 N6 C11 C16 -173.40(16) . . . . ?
C12 N6 C13 C14 173.77(19) . . . . ?
C13 N6 C11 C4 -177.38(17) . . . . ?
C13 N6 C11 C16 2.4(3) . . . . ?
C13 N6 C12 C3 114.78(19) . . . . ?
C13 C14 C15 C16 3.3(3) . . . . ?
C14 C15 C16 C11 -2.9(3) . . . . ?
C17 C2 C3 N1 -55.1(3) . . . . ?
C17 C2 C3 C12 121.2(2) . . . . ?
C17 C18 C19 C20 1.6(3) . . . . ?
C18 C19 C20 C1 0.7(3) . . . . ?
C20 C1 C2 C3 -179.22(18) . . . . ?
C20 C1 C2 C17 1.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xb1940
_database_code_depnum_ccdc_archive 'CCDC 1944957'
loop_
_audit_author_name
_audit_author_address
LL
;Northwest University
China
;
_audit_update_record             
;
2019-08-02 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;
_audit_creation_date             2019-03-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'I, C22 H16 N7'
_chemical_formula_sum            'C22 H16 I N7'
_chemical_formula_weight         505.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   21.618(3)
_cell_length_b                   7.8792(10)
_cell_length_c                   23.619(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4023.2(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1880
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      17.73
_cell_measurement_theta_min      2.55
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.617
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0699 before and 0.0515 after correction. The Ratio of minimum to maximum transmission is 0.9199. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0780
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            20750
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.240
_diffrn_reflns_theta_min         1.884
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2283
_reflns_number_total             4042
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.967
_refine_diff_density_min         -0.894
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4042
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0458P)²+1.1789P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1206
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), N4(H4), C4(H4A), C5(H5), C10(H10), C12(H12), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.39329(2) 0.39431(5) 0.52795(2) 0.06557(19) Uani 1 1 d . . . . .
N1 N 0.37380(18) 0.6328(5) 0.28952(17) 0.0424(11) Uani 1 1 d . . . . .
N2 N 0.31839(18) 0.6058(5) 0.31820(16) 0.0411(10) Uani 1 1 d . . . . .
N3 N 0.3970(2) 0.7146(5) 0.41575(16) 0.0430(10) Uani 1 1 d . . . . .
C1 C 0.4245(2) 0.6181(6) 0.31850(19) 0.0386(12) Uani 1 1 d . . . . .
C2 C 0.5408(2) 0.6005(6) 0.3055(2) 0.0468(13) Uani 1 1 d . . . . .
H2 H 0.551549 0.583297 0.343212 0.056 Uiso 1 1 calc R . . . .
C3 C 0.2634(2) 0.4789(6) 0.2331(2) 0.0424(13) Uani 1 1 d . . . . .
N4 N 0.5805(2) 0.5989(5) 0.26198(18) 0.0496(11) Uani 1 1 d . . . . .
H4 H 0.619683 0.582165 0.264538 0.060 Uiso 1 1 calc R . . . .
C4 C 0.2509(3) 0.3590(7) 0.1259(2) 0.0605(16) Uani 1 1 d . . . . .
H4A H 0.245093 0.320496 0.089056 0.073 Uiso 1 1 calc R . . . .
C5 C 0.4656(3) 0.6979(7) 0.1278(2) 0.0537(15) Uani 1 1 d . . . . .
H5 H 0.437791 0.722056 0.098834 0.064 Uiso 1 1 calc R . . . .
C6 C 0.4250(2) 0.5776(7) 0.38108(19) 0.0452(14) Uani 1 1 d . . . . .
H6A H 0.402328 0.473002 0.387431 0.054 Uiso 1 1 calc R . . . .
H6B H 0.467309 0.559611 0.393282 0.054 Uiso 1 1 calc R . . . .
C7 C 0.4861(2) 0.6489(6) 0.22572(19) 0.0363(12) Uani 1 1 d . . . . .
N5 N 0.20669(19) 0.4810(6) 0.20985(18) 0.0474(11) Uani 1 1 d . . . . .
C8 C 0.5482(2) 0.6285(6) 0.2120(2) 0.0418(13) Uani 1 1 d . . . . .
C9 C 0.4811(2) 0.6316(6) 0.28625(19) 0.0398(12) Uani 1 1 d . . . . .
N6 N 0.2383(2) 0.6339(6) 0.37478(19) 0.0627(14) Uani 1 1 d . . . . .
C10 C 0.4439(2) 0.6860(7) 0.1827(2) 0.0455(13) Uani 1 1 d . . . . .
H10 H 0.402218 0.702251 0.190787 0.055 Uiso 1 1 calc R . . . .
C11 C 0.2982(3) 0.6592(7) 0.3702(2) 0.0477(14) Uani 1 1 d . . . . .
C12 C 0.3146(3) 0.4169(6) 0.2046(2) 0.0537(15) Uani 1 1 d . . . . .
H12 H 0.353161 0.416185 0.222015 0.064 Uiso 1 1 calc R . . . .
C13 C 0.2661(2) 0.5473(6) 0.2908(2) 0.0439(13) Uani 1 1 d . . . . .
N7 N 0.2182(2) 0.5613(6) 0.3250(2) 0.0624(14) Uani 1 1 d . . . . .
C14 C 0.3077(3) 0.3562(7) 0.1502(2) 0.0600(16) Uani 1 1 d . . . . .
H14 H 0.341624 0.313944 0.130429 0.072 Uiso 1 1 calc R . . . .
C15 C 0.2016(3) 0.4204(7) 0.1572(2) 0.0577(16) Uani 1 1 d . . . . .
H15 H 0.162641 0.419470 0.140631 0.069 Uiso 1 1 calc R . . . .
C16 C 0.4328(3) 0.7948(7) 0.4542(2) 0.0563(16) Uani 1 1 d . . . . .
H16 H 0.475030 0.772252 0.455871 0.068 Uiso 1 1 calc R . . . .
C17 C 0.3353(3) 0.7415(7) 0.4135(2) 0.0467(13) Uani 1 1 d . . . . .
C18 C 0.5269(3) 0.6751(7) 0.1147(2) 0.0533(15) Uani 1 1 d . . . . .
H18 H 0.539638 0.683645 0.077193 0.064 Uiso 1 1 calc R . . . .
C19 C 0.4068(4) 0.9098(8) 0.4907(3) 0.069(2) Uani 1 1 d . . . . .
H19 H 0.431782 0.970317 0.515609 0.083 Uiso 1 1 calc R . . . .
C20 C 0.5703(3) 0.6395(7) 0.1563(2) 0.0516(14) Uani 1 1 d . . . . .
H20 H 0.611843 0.623672 0.147745 0.062 Uiso 1 1 calc R . . . .
C21 C 0.3440(4) 0.9359(8) 0.4907(2) 0.072(2) Uani 1 1 d . . . . .
H21 H 0.326046 1.011923 0.515978 0.087 Uiso 1 1 calc R . . . .
C22 C 0.3077(3) 0.8473(7) 0.4524(2) 0.0599(16) Uani 1 1 d . . . . .
H22 H 0.264911 0.859311 0.452977 0.072 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.393(5) . ?
N1 C1 1.298(6) . ?
N2 C11 1.370(6) . ?
N2 C13 1.381(6) . ?
N3 C6 1.484(6) . ?
N3 C16 1.351(6) . ?
N3 C17 1.352(6) . ?
C1 C6 1.512(6) . ?
C1 C9 1.444(7) . ?
C2 H2 0.9300 . ?
C2 N4 1.340(6) . ?
C2 C9 1.390(7) . ?
C3 N5 1.343(6) . ?
C3 C12 1.384(7) . ?
C3 C13 1.467(7) . ?
N4 H4 0.8600 . ?
N4 C8 1.391(6) . ?
C4 H4A 0.9300 . ?
C4 C14 1.357(7) . ?
C4 C15 1.383(8) . ?
C5 H5 0.9300 . ?
C5 C10 1.382(7) . ?
C5 C18 1.373(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.391(7) . ?
C7 C9 1.440(6) . ?
C7 C10 1.397(6) . ?
N5 C15 1.336(7) . ?
C8 C20 1.400(7) . ?
N6 C11 1.316(7) . ?
N6 N7 1.377(6) . ?
C10 H10 0.9300 . ?
C11 C17 1.452(7) . ?
C12 H12 0.9300 . ?
C12 C14 1.380(7) . ?
C13 N7 1.318(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C16 C19 1.372(8) . ?
C17 C22 1.376(7) . ?
C18 H18 0.9300 . ?
C18 C20 1.387(7) . ?
C19 H19 0.9300 . ?
C19 C21 1.374(9) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C21 C22 1.386(9) . ?
C22 H22 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 117.2(4) . . ?
C11 N2 N1 131.6(4) . . ?
C11 N2 C13 105.2(4) . . ?
C13 N2 N1 121.8(4) . . ?
C16 N3 C6 118.5(5) . . ?
C16 N3 C17 121.3(5) . . ?
C17 N3 C6 119.7(4) . . ?
N1 C1 C6 122.7(5) . . ?
N1 C1 C9 115.5(4) . . ?
C9 C1 C6 121.7(4) . . ?
N4 C2 H2 124.9 . . ?
N4 C2 C9 110.2(4) . . ?
C9 C2 H2 124.9 . . ?
N5 C3 C12 122.4(5) . . ?
N5 C3 C13 114.4(5) . . ?
C12 C3 C13 123.3(5) . . ?
C2 N4 H4 125.4 . . ?
C2 N4 C8 109.2(4) . . ?
C8 N4 H4 125.4 . . ?
C14 C4 H4A 120.8 . . ?
C14 C4 C15 118.5(5) . . ?
C15 C4 H4A 120.8 . . ?
C10 C5 H5 119.0 . . ?
C18 C5 H5 119.0 . . ?
C18 C5 C10 122.0(5) . . ?
N3 C6 C1 112.5(4) . . ?
N3 C6 H6A 109.1 . . ?
N3 C6 H6B 109.1 . . ?
C1 C6 H6A 109.1 . . ?
C1 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C9 107.1(4) . . ?
C8 C7 C10 119.0(4) . . ?
C10 C7 C9 133.8(5) . . ?
C15 N5 C3 116.8(5) . . ?
N4 C8 C7 107.7(4) . . ?
N4 C8 C20 129.6(5) . . ?
C7 C8 C20 122.7(5) . . ?
C2 C9 C1 126.8(4) . . ?
C2 C9 C7 105.8(4) . . ?
C7 C9 C1 126.5(4) . . ?
C11 N6 N7 107.7(4) . . ?
C5 C10 C7 118.4(5) . . ?
C5 C10 H10 120.8 . . ?
C7 C10 H10 120.8 . . ?
N2 C11 C17 126.4(5) . . ?
N6 C11 N2 109.9(5) . . ?
N6 C11 C17 123.6(5) . . ?
C3 C12 H12 120.3 . . ?
C14 C12 C3 119.3(5) . . ?
C14 C12 H12 120.3 . . ?
N2 C13 C3 126.2(5) . . ?
N7 C13 N2 109.2(5) . . ?
N7 C13 C3 124.6(5) . . ?
C13 N7 N6 108.0(4) . . ?
C4 C14 C12 119.0(5) . . ?
C4 C14 H14 120.5 . . ?
C12 C14 H14 120.5 . . ?
C4 C15 H15 118.0 . . ?
N5 C15 C4 124.0(5) . . ?
N5 C15 H15 118.0 . . ?
N3 C16 H16 120.1 . . ?
N3 C16 C19 119.7(6) . . ?
C19 C16 H16 120.1 . . ?
N3 C17 C11 120.1(5) . . ?
N3 C17 C22 119.8(5) . . ?
C22 C17 C11 120.1(5) . . ?
C5 C18 H18 119.4 . . ?
C5 C18 C20 121.3(5) . . ?
C20 C18 H18 119.4 . . ?
C16 C19 H19 119.8 . . ?
C16 C19 C21 120.3(6) . . ?
C21 C19 H19 119.8 . . ?
C8 C20 H20 121.7 . . ?
C18 C20 C8 116.6(5) . . ?
C18 C20 H20 121.7 . . ?
C19 C21 H21 120.5 . . ?
C19 C21 C22 118.9(6) . . ?
C22 C21 H21 120.5 . . ?
C17 C22 C21 119.7(6) . . ?
C17 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?

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
N1 N2 C11 N6 166.6(5) . . . . ?
N1 N2 C11 C17 -9.9(9) . . . . ?
N1 N2 C13 C3 11.2(8) . . . . ?
N1 N2 C13 N7 -169.1(4) . . . . ?
N1 C1 C6 N3 -65.2(7) . . . . ?
N1 C1 C9 C2 -171.7(5) . . . . ?
N1 C1 C9 C7 -4.2(8) . . . . ?
N2 N1 C1 C6 -1.5(7) . . . . ?
N2 N1 C1 C9 174.6(4) . . . . ?
N2 C11 C17 N3 -26.1(8) . . . . ?
N2 C11 C17 C22 153.8(5) . . . . ?
N2 C13 N7 N6 1.7(6) . . . . ?
N3 C16 C19 C21 4.0(9) . . . . ?
N3 C17 C22 C21 5.1(8) . . . . ?
C1 N1 N2 C11 44.0(7) . . . . ?
C1 N1 N2 C13 -152.0(5) . . . . ?
C2 N4 C8 C7 0.0(6) . . . . ?
C2 N4 C8 C20 179.4(5) . . . . ?
C3 N5 C15 C4 -0.8(8) . . . . ?
C3 C12 C14 C4 0.0(8) . . . . ?
C3 C13 N7 N6 -178.6(5) . . . . ?
N4 C2 C9 C1 170.0(5) . . . . ?
N4 C2 C9 C7 0.4(6) . . . . ?
N4 C8 C20 C18 -178.3(5) . . . . ?
C5 C18 C20 C8 -0.1(8) . . . . ?
C6 N3 C16 C19 -173.4(5) . . . . ?
C6 N3 C17 C11 -11.4(7) . . . . ?
C6 N3 C17 C22 168.8(4) . . . . ?
C6 C1 C9 C2 4.4(8) . . . . ?
C6 C1 C9 C7 171.9(5) . . . . ?
C7 C8 C20 C18 1.0(8) . . . . ?
N5 C3 C12 C14 0.6(8) . . . . ?
N5 C3 C13 N2 -159.9(5) . . . . ?
N5 C3 C13 N7 20.5(8) . . . . ?
C8 C7 C9 C1 -170.0(5) . . . . ?
C8 C7 C9 C2 -0.4(6) . . . . ?
C8 C7 C10 C5 1.1(8) . . . . ?
C9 C1 C6 N3 119.0(5) . . . . ?
C9 C2 N4 C8 -0.2(6) . . . . ?
C9 C7 C8 N4 0.3(5) . . . . ?
C9 C7 C8 C20 -179.2(5) . . . . ?
C9 C7 C10 C5 178.0(6) . . . . ?
N6 C11 C17 N3 157.9(5) . . . . ?
N6 C11 C17 C22 -22.2(8) . . . . ?
C10 C5 C18 C20 -0.3(9) . . . . ?
C10 C7 C8 N4 177.9(4) . . . . ?
C10 C7 C8 C20 -1.6(7) . . . . ?
C10 C7 C9 C1 12.8(10) . . . . ?
C10 C7 C9 C2 -177.5(5) . . . . ?
C11 N2 C13 C3 178.9(5) . . . . ?
C11 N2 C13 N7 -1.4(6) . . . . ?
C11 N6 N7 C13 -1.3(6) . . . . ?
C11 C17 C22 C21 -174.8(5) . . . . ?
C12 C3 N5 C15 -0.3(8) . . . . ?
C12 C3 C13 N2 20.3(8) . . . . ?
C12 C3 C13 N7 -159.4(5) . . . . ?
C13 N2 C11 N6 0.6(6) . . . . ?
C13 N2 C11 C17 -175.9(5) . . . . ?
C13 C3 N5 C15 179.9(4) . . . . ?
C13 C3 C12 C14 -179.5(5) . . . . ?
N7 N6 C11 N2 0.4(6) . . . . ?
N7 N6 C11 C17 177.0(5) . . . . ?
C14 C4 C15 N5 1.5(9) . . . . ?
C15 C4 C14 C12 -1.0(8) . . . . ?
C16 N3 C6 C1 -117.8(5) . . . . ?
C16 N3 C17 C11 177.3(4) . . . . ?
C16 N3 C17 C22 -2.5(7) . . . . ?
C16 C19 C21 C22 -1.4(9) . . . . ?
C17 N3 C6 C1 70.6(6) . . . . ?
C17 N3 C16 C19 -2.0(7) . . . . ?
C18 C5 C10 C7 -0.2(8) . . . . ?
C19 C21 C22 C17 -3.1(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sust_2192_lx_0ma_sq
_database_code_depnum_ccdc_archive 'CCDC 1944956'
loop_
_audit_author_name
_audit_author_address
LL
;Northwest University
China
;
_audit_update_record             
;
2019-08-02 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;
_audit_creation_date             2019-01-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'I, C20 H15 N6 O'
_chemical_formula_sum            'C20 H15 I N6 O'
_chemical_formula_weight         482.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.0435(6)
_cell_length_b                   11.5711(10)
_cell_length_c                   27.338(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.054(5)
_cell_angle_gamma                90
_cell_volume                     2534.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5200
_cell_measurement_temperature    293
_cell_measurement_theta_max      22.25
_cell_measurement_theta_min      2.85
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.281
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0718 before and 0.0593 after correction. The Ratio of minimum to maximum transmission is 0.8698. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1080
_diffrn_reflns_av_unetI/netI     0.1021
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            26413
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.399
_diffrn_reflns_theta_min         2.542
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3267
_reflns_number_total             6311
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.966
_refine_diff_density_min         -0.762
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         6311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1421
_refine_ls_R_factor_gt           0.0722
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0780P)²+3.9012P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1699
_refine_ls_wR_factor_ref         0.1942
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.73366(6) 0.62473(5) 0.39781(2) 0.0659(2) Uani 1 1 d . . . . .
O1 O 0.0831(7) 0.2187(4) 0.28187(19) 0.0662(14) Uani 1 1 d . . . . .
H1 H 0.110559 0.161959 0.298650 0.099 Uiso 1 1 calc GR . . . .
N1 N 0.1920(6) 0.7296(4) 0.35527(16) 0.0363(11) Uani 1 1 d . . . . .
N2 N 0.2132(6) 0.8324(4) 0.38114(16) 0.0309(10) Uani 1 1 d . . . . .
N3 N 0.1600(6) 0.9799(4) 0.42845(17) 0.0390(12) Uani 1 1 d . . . . .
N4 N 0.2201(6) 1.0230(4) 0.38696(17) 0.0381(11) Uani 1 1 d . . . . .
N5 N 0.2919(6) 1.0378(4) 0.28563(17) 0.0403(12) Uani 1 1 d . . . . .
N6 N 0.1729(5) 0.6839(4) 0.46820(15) 0.0317(10) Uani 1 1 d . . . . .
C1 C 0.1226(8) 0.3170(5) 0.3081(2) 0.0453(15) Uani 1 1 d . . . . .
C2 C 0.2246(8) 0.3173(6) 0.3498(2) 0.0453(15) Uani 1 1 d . . . . .
H2 H 0.271809 0.248777 0.362226 0.054 Uiso 1 1 calc R . . . .
C3 C 0.2590(8) 0.4220(5) 0.3742(2) 0.0433(15) Uani 1 1 d . . . . .
H3 H 0.331920 0.422184 0.402569 0.052 Uiso 1 1 calc R . . . .
C4 C 0.1873(7) 0.5268(5) 0.3574(2) 0.0358(13) Uani 1 1 d . . . . .
C5 C 0.2214(7) 0.6383(5) 0.3811(2) 0.0339(12) Uani 1 1 d . . . . .
C6 C 0.1583(7) 0.8667(5) 0.4247(2) 0.0337(12) Uani 1 1 d . . . . .
C7 C 0.2524(7) 0.9345(5) 0.3591(2) 0.0355(13) Uani 1 1 d . . . . .
C8 C 0.3297(7) 0.9407(5) 0.3115(2) 0.0365(13) Uani 1 1 d . . . . .
C9 C 0.3608(9) 1.0475(6) 0.2429(2) 0.0522(17) Uani 1 1 d . . . . .
H9 H 0.336036 1.112535 0.223579 0.063 Uiso 1 1 calc R . . . .
C10 C 0.4672(10) 0.9650(6) 0.2261(3) 0.065(2) Uani 1 1 d . . . . .
H10 H 0.515222 0.976690 0.196812 0.078 Uiso 1 1 calc R . . . .
C11 C 0.5016(10) 0.8663(7) 0.2527(3) 0.078(3) Uani 1 1 d . . . . .
H11 H 0.569648 0.808881 0.241437 0.094 Uiso 1 1 calc R . . . .
C12 C 0.4306(9) 0.8549(6) 0.2973(3) 0.059(2) Uani 1 1 d . . . . .
H12 H 0.451994 0.789902 0.316836 0.071 Uiso 1 1 calc R . . . .
C13 C 0.1043(7) 0.7899(5) 0.46249(18) 0.0309(12) Uani 1 1 d . . . . .
C14 C 0.2959(7) 0.6463(5) 0.4342(2) 0.0346(13) Uani 1 1 d . . . . .
H14A H 0.339826 0.571286 0.444564 0.042 Uiso 1 1 calc R . . . .
H14B H 0.388140 0.700554 0.436140 0.042 Uiso 1 1 calc R . . . .
C15 C 0.1386(8) 0.6145(5) 0.5055(2) 0.0425(14) Uani 1 1 d . . . . .
H15 H 0.183974 0.540632 0.508200 0.051 Uiso 1 1 calc R . . . .
C16 C 0.0353(9) 0.6537(6) 0.5399(2) 0.0528(18) Uani 1 1 d . . . . .
H16 H 0.014177 0.606639 0.566250 0.063 Uiso 1 1 calc R . . . .
C17 C -0.0350(8) 0.7598(6) 0.5356(2) 0.0494(17) Uani 1 1 d . . . . .
H17 H -0.104365 0.786154 0.558657 0.059 Uiso 1 1 calc R . . . .
C18 C -0.0021(7) 0.8282(5) 0.4963(2) 0.0387(14) Uani 1 1 d . . . . .
H18 H -0.051616 0.900603 0.492396 0.046 Uiso 1 1 calc R . . . .
C19 C 0.0791(8) 0.5199(5) 0.3152(2) 0.0507(17) Uani 1 1 d . . . . .
H19 H 0.025412 0.586838 0.303445 0.061 Uiso 1 1 calc R . . . .
C20 C 0.0478(9) 0.4184(6) 0.2900(3) 0.061(2) Uani 1 1 d . . . . .
H20 H -0.022652 0.417570 0.261132 0.074 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C1 1.367(7) . ?
N1 N2 1.386(6) . ?
N1 C5 1.282(7) . ?
N2 C6 1.364(7) . ?
N2 C7 1.376(7) . ?
N3 N4 1.366(6) . ?
N3 C6 1.314(7) . ?
N4 C7 1.316(7) . ?
N5 C8 1.349(7) . ?
N5 C9 1.342(7) . ?
N6 C13 1.349(7) . ?
N6 C14 1.481(7) . ?
N6 C15 1.346(7) . ?
C1 C2 1.344(9) . ?
C1 C20 1.391(9) . ?
C2 H2 0.9300 . ?
C2 C3 1.400(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.402(8) . ?
C4 C5 1.460(8) . ?
C4 C19 1.384(8) . ?
C5 C14 1.523(8) . ?
C6 C13 1.458(8) . ?
C7 C8 1.490(7) . ?
C8 C12 1.361(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.387(9) . ?
C10 H10 0.9300 . ?
C10 C11 1.368(10) . ?
C11 H11 0.9300 . ?
C11 C12 1.397(9) . ?
C12 H12 0.9300 . ?
C13 C18 1.386(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15 0.9300 . ?
C15 C16 1.384(9) . ?
C16 H16 0.9300 . ?
C16 C17 1.353(9) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(8) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C19 C20 1.374(9) . ?
C20 H20 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C5 N1 N2 114.7(5) . . ?
C6 N2 N1 131.3(4) . . ?
C6 N2 C7 103.7(4) . . ?
C7 N2 N1 122.4(4) . . ?
C6 N3 N4 107.5(4) . . ?
C7 N4 N3 107.4(4) . . ?
C9 N5 C8 115.9(5) . . ?
C13 N6 C14 118.9(4) . . ?
C15 N6 C13 121.4(5) . . ?
C15 N6 C14 119.6(5) . . ?
O1 C1 C20 116.2(6) . . ?
C2 C1 O1 122.9(6) . . ?
C2 C1 C20 120.9(6) . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.1(6) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 118.9 . . ?
C2 C3 C4 122.3(6) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 C5 124.2(6) . . ?
C19 C4 C3 115.7(6) . . ?
C19 C4 C5 120.0(5) . . ?
N1 C5 C4 117.7(5) . . ?
N1 C5 C14 120.9(5) . . ?
C4 C5 C14 121.4(5) . . ?
N2 C6 C13 125.5(5) . . ?
N3 C6 N2 110.9(5) . . ?
N3 C6 C13 123.6(5) . . ?
N2 C7 C8 123.6(5) . . ?
N4 C7 N2 110.4(5) . . ?
N4 C7 C8 125.9(5) . . ?
N5 C8 C7 114.0(5) . . ?
N5 C8 C12 124.7(5) . . ?
C12 C8 C7 121.3(5) . . ?
N5 C9 H9 118.5 . . ?
N5 C9 C10 122.9(6) . . ?
C10 C9 H9 118.5 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.1(6) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 121.2 . . ?
C10 C11 C12 117.6(7) . . ?
C12 C11 H11 121.2 . . ?
C8 C12 C11 118.8(6) . . ?
C8 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
N6 C13 C6 119.5(5) . . ?
N6 C13 C18 118.9(5) . . ?
C18 C13 C6 121.2(5) . . ?
N6 C14 C5 112.8(4) . . ?
N6 C14 H14A 109.0 . . ?
N6 C14 H14B 109.0 . . ?
C5 C14 H14A 109.0 . . ?
C5 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
N6 C15 H15 120.2 . . ?
N6 C15 C16 119.7(6) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.6(6) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.6 . . ?
C16 C17 C18 118.8(6) . . ?
C18 C17 H17 120.6 . . ?
C13 C18 H18 119.7 . . ?
C17 C18 C13 120.5(6) . . ?
C17 C18 H18 119.7 . . ?
C4 C19 H19 118.6 . . ?
C20 C19 C4 122.7(6) . . ?
C20 C19 H19 118.6 . . ?
C1 C20 H20 120.4 . . ?
C19 C20 C1 119.2(6) . . ?
C19 C20 H20 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 179.6(6) . . . . ?
O1 C1 C20 C19 178.6(7) . . . . ?
N1 N2 C6 N3 -160.0(5) . . . . ?
N1 N2 C6 C13 20.0(9) . . . . ?
N1 N2 C7 N4 162.3(5) . . . . ?
N1 N2 C7 C8 -20.9(8) . . . . ?
N1 C5 C14 N6 75.7(6) . . . . ?
N2 N1 C5 C4 174.6(4) . . . . ?
N2 N1 C5 C14 -7.8(7) . . . . ?
N2 C6 C13 N6 30.6(8) . . . . ?
N2 C6 C13 C18 -156.7(5) . . . . ?
N2 C7 C8 N5 151.9(5) . . . . ?
N2 C7 C8 C12 -29.0(9) . . . . ?
N3 N4 C7 N2 0.5(6) . . . . ?
N3 N4 C7 C8 -176.1(5) . . . . ?
N3 C6 C13 N6 -149.4(5) . . . . ?
N3 C6 C13 C18 23.2(9) . . . . ?
N4 N3 C6 N2 -1.1(6) . . . . ?
N4 N3 C6 C13 178.9(5) . . . . ?
N4 C7 C8 N5 -31.9(8) . . . . ?
N4 C7 C8 C12 147.2(7) . . . . ?
N5 C8 C12 C11 -0.1(12) . . . . ?
N5 C9 C10 C11 2.4(13) . . . . ?
N6 C13 C18 C17 1.1(9) . . . . ?
N6 C15 C16 C17 1.9(10) . . . . ?
C1 C2 C3 C4 1.6(9) . . . . ?
C2 C1 C20 C19 -0.1(11) . . . . ?
C2 C3 C4 C5 -179.0(5) . . . . ?
C2 C3 C4 C19 0.5(8) . . . . ?
C3 C4 C5 N1 158.8(5) . . . . ?
C3 C4 C5 C14 -18.8(8) . . . . ?
C3 C4 C19 C20 -2.4(10) . . . . ?
C4 C5 C14 N6 -106.8(5) . . . . ?
C4 C19 C20 C1 2.3(11) . . . . ?
C5 N1 N2 C6 -47.8(8) . . . . ?
C5 N1 N2 C7 153.7(5) . . . . ?
C5 C4 C19 C20 177.1(6) . . . . ?
C6 N2 C7 N4 -1.2(6) . . . . ?
C6 N2 C7 C8 175.6(5) . . . . ?
C6 N3 N4 C7 0.3(6) . . . . ?
C6 C13 C18 C17 -171.6(5) . . . . ?
C7 N2 C6 N3 1.4(6) . . . . ?
C7 N2 C6 C13 -178.7(5) . . . . ?
C7 C8 C12 C11 -179.0(7) . . . . ?
C8 N5 C9 C10 -1.3(10) . . . . ?
C9 N5 C8 C7 179.2(5) . . . . ?
C9 N5 C8 C12 0.1(9) . . . . ?
C9 C10 C11 C12 -2.2(13) . . . . ?
C10 C11 C12 C8 1.1(13) . . . . ?
C13 N6 C14 C5 -63.1(6) . . . . ?
C13 N6 C15 C16 -2.3(9) . . . . ?
C14 N6 C13 C6 -2.8(7) . . . . ?
C14 N6 C13 C18 -175.7(5) . . . . ?
C14 N6 C15 C16 174.2(6) . . . . ?
C15 N6 C13 C6 173.6(5) . . . . ?
C15 N6 C13 C18 0.8(8) . . . . ?
C15 N6 C14 C5 120.3(6) . . . . ?
C15 C16 C17 C18 0.0(11) . . . . ?
C16 C17 C18 C13 -1.5(10) . . . . ?
C19 C4 C5 N1 -20.6(8) . . . . ?
C19 C4 C5 C14 161.8(5) . . . . ?
C20 C1 C2 C3 -1.8(10) . . . . ?

_platon_squeeze_details          ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.500 0.000 415 142 ' '
2 0.500 0.000 0.500 415 142 ' '

_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
