# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_rs8d3
_database_code_depnum_ccdc_archive 'CCDC 2079261'
loop_
_audit_author_name
_audit_author_address
'Ian Walton'
;Georgia Institute of Technology
United States of America
;

_audit_update_record             
;
2021-04-21 deposited with the CCDC.	2022-09-30 downloaded from the CCDC.
;
# publcif _publ_body_element loop end
_audit_creation_date             2020-11-16
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6197)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        Zn(purine)Br
_chemical_formula_moiety         'C10 H6 Br2 N8 Zn2'
_chemical_formula_sum            'C10 H6 Br2 N8 Zn2'
_chemical_formula_weight         528.79
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br 0.2863 0.9639 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0005 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2605 0.5371 '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/n 1'
_space_group_name_Hall           '-P 2yn'
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                   13.8144(7)
_cell_length_b                   10.1970(5)
_cell_length_c                   13.8537(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.3260(10)
_cell_angle_gamma                90
_cell_volume                     1950.99(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9483
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      17.19
_cell_measurement_theta_min      2.25
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.908
_exptl_absorpt_coefficient_mu    1.509
_exptl_absorpt_correction_T_max  0.7441
_exptl_absorpt_correction_T_min  0.6507
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1296 before and 0.0450 after correction.
The Ratio of minimum to maximum transmission is 0.8745.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.800
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1008
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.06512
_exptl_crystal_size_mid          0.02671
_exptl_crystal_size_min          0.0239
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            57752
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        14.357
_diffrn_reflns_theta_max         17.199
_diffrn_reflns_theta_min         1.197
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Pilatus3 X CdTe 1M'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.41328
_diffrn_source                   ?
_diffrn_source_current           103.0
_diffrn_source_power             103.0
_diffrn_source_voltage           1000.0
_diffrn_standards_number         0
_diffrn_Standards_interval_time  0
_difffn_standards_decay_%        0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5026
_reflns_number_total             5844
_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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.319
_refine_diff_density_min         -1.315
_refine_diff_density_rms         0.128
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         5844
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.112
_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)+(0.0215P)²+6.2036P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0718
_refine_ls_wR_factor_ref         0.0776
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C5(H5), C7(H7), C1(H1), C6(H6), C2(H2)
;
_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
Br1 Br 0.71201(3) -0.00510(3) 0.49884(2) 0.02939(8) Uani 1 1 d . . . . .
Zn1 Zn 0.68726(2) 0.08527(3) 0.34480(2) 0.01502(7) Uani 1 1 d . . . . .
Br2 Br 0.00125(2) 0.09064(3) 0.18369(3) 0.02901(8) Uani 1 1 d . . . . .
Zn2 Zn 0.15761(2) 0.00064(3) 0.18152(2) 0.01530(7) Uani 1 1 d . . . . .
N7 N 0.25769(17) 0.1190(2) 0.24121(17) 0.0169(4) Uani 1 1 d . . . . .
N4 N 0.72609(17) 0.2729(2) 0.33026(17) 0.0168(4) Uani 1 1 d . . . . .
N8 N 0.32722(17) 0.3121(2) 0.28419(17) 0.0177(4) Uani 1 1 d . . . . .
N3 N 0.76879(17) 0.4649(2) 0.25965(17) 0.0169(4) Uani 1 1 d . . . . .
N2 N 0.75560(18) 0.6054(2) 0.39991(17) 0.0185(4) Uani 1 1 d . . . . .
N5 N 0.54158(18) 0.0984(2) 0.31294(18) 0.0197(5) Uani 1 1 d . . . . .
N1 N 0.70061(18) 0.4924(2) 0.54016(17) 0.0180(4) Uani 1 1 d . . . . .
N6 N 0.39952(18) -0.0196(2) 0.26047(18) 0.0196(5) Uani 1 1 d . . . . .
C10 C 0.2466(2) 0.2485(3) 0.2552(2) 0.0193(5) Uani 1 1 d . . . . .
H10 H 0.186226 0.291703 0.245416 0.023 Uiso 1 1 calc R U . . .
C9 C 0.35334(19) 0.0959(3) 0.26271(19) 0.0164(5) Uani 1 1 d . . . . .
C4 C 0.75087(19) 0.4900(3) 0.3545(2) 0.0168(5) Uani 1 1 d . . . . .
C5 C 0.7529(2) 0.3354(3) 0.2495(2) 0.0188(5) Uani 1 1 d . . . . .
H5 H 0.760080 0.291256 0.189708 0.023 Uiso 1 1 calc R U . . .
C3 C 0.72405(19) 0.3711(2) 0.3987(2) 0.0164(5) Uani 1 1 d . . . . .
C8 C 0.3970(2) 0.2153(3) 0.28995(19) 0.0172(5) Uani 1 1 d . . . . .
C7 C 0.4942(2) 0.2142(3) 0.3142(2) 0.0177(5) Uani 1 1 d . . . . .
H7 H 0.527177 0.292876 0.331284 0.021 Uiso 1 1 calc R U . . .
C1 C 0.7292(2) 0.5999(3) 0.4913(2) 0.0194(5) Uani 1 1 d . . . . .
H1 H 0.730548 0.680134 0.526114 0.023 Uiso 1 1 calc R U . . .
C6 C 0.4923(2) -0.0115(3) 0.2869(2) 0.0206(5) Uani 1 1 d . . . . .
H6 H 0.527919 -0.091144 0.287618 0.025 Uiso 1 1 calc R U . . .
C2 C 0.6974(2) 0.3754(3) 0.4943(2) 0.0176(5) Uani 1 1 d . . . . .
H2 H 0.677516 0.298321 0.526824 0.021 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
Br1 Zn1 2.3423(4) . ?
Zn1 N4 1.999(2) . ?
Zn1 N3 2.002(2) 2_645 ?
Zn1 N5 2.055(2) . ?
Br2 Zn2 2.3476(4) . ?
Zn2 N7 2.000(2) . ?
Zn2 N8 1.990(2) 2_545 ?
Zn2 N1 2.061(2) 4_565 ?
N7 C10 1.344(3) . ?
N7 C9 1.368(3) . ?
N4 C5 1.347(4) . ?
N4 C3 1.380(3) . ?
N8 C10 1.342(4) . ?
N8 C8 1.381(3) . ?
N3 C4 1.367(3) . ?
N3 C5 1.346(3) . ?
N2 C4 1.335(3) . ?
N2 C1 1.326(4) . ?
N5 C7 1.350(3) . ?
N5 C6 1.356(4) . ?
N1 C1 1.352(3) . ?
N1 C2 1.352(3) . ?
N6 C9 1.340(3) . ?
N6 C6 1.327(4) . ?
C10 H10 0.9500 . ?
C9 C8 1.407(4) . ?
C4 C3 1.412(3) . ?
C5 H5 0.9500 . ?
C3 C2 1.383(4) . ?
C8 C7 1.376(4) . ?
C7 H7 0.9500 . ?
C1 H1 0.9500 . ?
C6 H6 0.9500 . ?
C2 H2 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
N4 Zn1 Br1 115.76(7) . . ?
N4 Zn1 N3 115.29(9) . 2_645 ?
N4 Zn1 N5 100.35(10) . . ?
N3 Zn1 Br1 112.15(7) 2_645 . ?
N3 Zn1 N5 101.34(10) 2_645 . ?
N5 Zn1 Br1 110.06(7) . . ?
N7 Zn2 Br2 112.73(7) . . ?
N7 Zn2 N1 99.24(10) . 4_565 ?
N8 Zn2 Br2 117.80(7) 2_545 . ?
N8 Zn2 N7 114.60(10) 2_545 . ?
N8 Zn2 N1 103.22(10) 2_545 4_565 ?
N1 Zn2 Br2 106.51(7) 4_565 . ?
C10 N7 Zn2 124.92(19) . . ?
C10 N7 C9 104.5(2) . . ?
C9 N7 Zn2 129.89(18) . . ?
C5 N4 Zn1 128.04(19) . . ?
C5 N4 C3 103.8(2) . . ?
C3 N4 Zn1 127.99(18) . . ?
C10 N8 Zn2 128.33(19) . 2 ?
C10 N8 C8 104.2(2) . . ?
C8 N8 Zn2 127.36(19) . 2 ?
C4 N3 Zn1 130.16(18) . 2_655 ?
C5 N3 Zn1 125.26(19) . 2_655 ?
C5 N3 C4 104.6(2) . . ?
C1 N2 C4 113.6(2) . . ?
C7 N5 Zn1 121.80(19) . . ?
C7 N5 C6 119.0(2) . . ?
C6 N5 Zn1 119.12(19) . . ?
C1 N1 Zn2 122.85(18) . 4_666 ?
C2 N1 Zn2 118.02(18) . 4_666 ?
C2 N1 C1 119.1(2) . . ?
C6 N6 C9 113.3(2) . . ?
N7 C10 H10 122.6 . . ?
N8 C10 N7 114.9(2) . . ?
N8 C10 H10 122.6 . . ?
N7 C9 C8 108.4(2) . . ?
N6 C9 N7 127.2(2) . . ?
N6 C9 C8 124.4(2) . . ?
N3 C4 C3 108.2(2) . . ?
N2 C4 N3 127.6(2) . . ?
N2 C4 C3 124.3(2) . . ?
N4 C5 H5 122.4 . . ?
N3 C5 N4 115.1(3) . . ?
N3 C5 H5 122.4 . . ?
N4 C3 C4 108.4(2) . . ?
N4 C3 C2 133.7(2) . . ?
C2 C3 C4 117.8(2) . . ?
N8 C8 C9 107.9(2) . . ?
C7 C8 N8 134.1(3) . . ?
C7 C8 C9 117.9(2) . . ?
N5 C7 C8 118.3(2) . . ?
N5 C7 H7 120.8 . . ?
C8 C7 H7 120.8 . . ?
N2 C1 N1 127.1(2) . . ?
N2 C1 H1 116.5 . . ?
N1 C1 H1 116.5 . . ?
N5 C6 H6 116.5 . . ?
N6 C6 N5 126.9(3) . . ?
N6 C6 H6 116.5 . . ?
N1 C2 C3 118.1(2) . . ?
N1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?

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
Zn1 N4 C5 N3 175.54(19) . . . . ?
Zn1 N4 C3 C4 -175.58(19) . . . . ?
Zn1 N4 C3 C2 0.5(5) . . . . ?
Zn1 N3 C4 N2 2.6(4) 2_655 . . . ?
Zn1 N3 C4 C3 -178.38(19) 2_655 . . . ?
Zn1 N3 C5 N4 178.28(19) 2_655 . . . ?
Zn1 N5 C7 C8 178.6(2) . . . . ?
Zn1 N5 C6 N6 -177.2(2) . . . . ?
Zn2 N7 C10 N8 -171.32(19) . . . . ?
Zn2 N7 C9 N6 -10.0(4) . . . . ?
Zn2 N7 C9 C8 170.99(19) . . . . ?
Zn2 N8 C10 N7 -177.16(19) 2 . . . ?
Zn2 N8 C8 C9 177.35(19) 2 . . . ?
Zn2 N8 C8 C7 -3.7(5) 2 . . . ?
Zn2 N1 C1 N2 -178.1(2) 4_666 . . . ?
Zn2 N1 C2 C3 178.5(2) 4_666 . . . ?
N7 C9 C8 N8 -0.4(3) . . . . ?
N7 C9 C8 C7 -179.6(2) . . . . ?
N4 C3 C2 N1 -177.1(3) . . . . ?
N8 C8 C7 N5 179.4(3) . . . . ?
N3 C4 C3 N4 0.3(3) . . . . ?
N3 C4 C3 C2 -176.5(2) . . . . ?
N2 C4 C3 N4 179.3(3) . . . . ?
N2 C4 C3 C2 2.5(4) . . . . ?
N6 C9 C8 N8 -179.5(3) . . . . ?
N6 C9 C8 C7 1.3(4) . . . . ?
C10 N7 C9 N6 179.3(3) . . . . ?
C10 N7 C9 C8 0.3(3) . . . . ?
C10 N8 C8 C9 0.4(3) . . . . ?
C10 N8 C8 C7 179.4(3) . . . . ?
C9 N7 C10 N8 0.0(3) . . . . ?
C9 N6 C6 N5 -1.1(4) . . . . ?
C9 C8 C7 N5 -1.7(4) . . . . ?
C4 N3 C5 N4 -0.1(3) . . . . ?
C4 N2 C1 N1 0.9(4) . . . . ?
C4 C3 C2 N1 -1.3(4) . . . . ?
C5 N4 C3 C4 -0.3(3) . . . . ?
C5 N4 C3 C2 175.8(3) . . . . ?
C5 N3 C4 N2 -179.1(3) . . . . ?
C5 N3 C4 C3 -0.1(3) . . . . ?
C3 N4 C5 N3 0.3(3) . . . . ?
C8 N8 C10 N7 -0.3(3) . . . . ?
C7 N5 C6 N6 0.7(5) . . . . ?
C1 N2 C4 N3 176.7(3) . . . . ?
C1 N2 C4 C3 -2.2(4) . . . . ?
C1 N1 C2 C3 0.1(4) . . . . ?
C6 N5 C7 C8 0.8(4) . . . . ?
C6 N6 C9 N7 -178.8(3) . . . . ?
C6 N6 C9 C8 0.1(4) . . . . ?
C2 N1 C1 N2 0.1(5) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 -0.904 0.500 261.7 64.5 ?
2 0.000 0.500 0.000 31.8 0.0 ?
3 0.500 -0.875 0.000 261.7 64.5 ?
4 0.500 0.000 0.500 31.8 0.0 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_exptl_crystal_mounting_method 'glass fiber with paratone oil'
_olex2_submission_special_instructions 'No special instructions were received'



_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_rs10d1
_database_code_depnum_ccdc_archive 'CCDC 2079262'
loop_
_audit_author_name
_audit_author_address
'Ian Walton'
;Georgia Institute of Technology
United States of America
;

_audit_update_record             
;
2021-04-21 deposited with the CCDC.	2022-09-30 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT213_RS10D1              
;
PROBLEM: Atom C1 has ADP max/min Ratio .......................4.2 prolat
RESPONSE: The larger ADP min/max ratio has been attributed to small size of the
 crystal, and the corresponding effect on the diffraction data. Given that only
 one atom is affected, the structure of the material is still considred valid.
;
# publcif _publ_body_element loop end
_audit_creation_date             2020-11-16
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6197)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        Zn(purine)I
_chemical_formula_moiety         'C10 H6 I2 N8 Zn2'
_chemical_formula_sum            'C10 H6 I2 N8 Zn2'
_chemical_formula_weight         622.77
_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 -0.0001 0.0005 '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 -1.9018 0.6867 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0005 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2605 0.5371 '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/n 1'
_space_group_name_Hall           '-P 2yn'
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                   14.0372(18)
_cell_length_b                   10.1884(13)
_cell_length_c                   14.0589(19)
_cell_angle_alpha                90
_cell_angle_beta                 92.057(3)
_cell_angle_gamma                90
_cell_volume                     2009.4(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3281
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      14.23
_cell_measurement_theta_min      2.19
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    1.247
_exptl_absorpt_correction_T_max  0.7439
_exptl_absorpt_correction_T_min  0.6573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1112 before and 0.0690 after correction.
The Ratio of minimum to maximum transmission is 0.8836.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.059
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.02242
_exptl_crystal_size_mid          0.02144
_exptl_crystal_size_min          0.01567
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1337
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            47951
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        14.357
_diffrn_reflns_theta_max         14.990
_diffrn_reflns_theta_min         1.171
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Pilatus3 X CdTe 1M'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.41328
_diffrn_source                   ?
_diffrn_source_current           103.0
_diffrn_source_power             103.0
_diffrn_source_voltage           1000.0
_diffrn_standards_number         0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3252
_reflns_number_total             4130
_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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.984
_refine_diff_density_min         -2.210
_refine_diff_density_rms         0.278
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         4130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.0789
_refine_ls_restrained_S_all      1.118
_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)+(0.0979P)²+31.9630P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1968
_refine_ls_wR_factor_ref         0.2071
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C10(H10), C2(H2), C1(H1), C6(H6), C7(H7)
;
_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
I2 I 0.82479(7) 1.10646(8) 0.50415(6) 0.0361(3) Uani 1 1 d . . . . .
I1 I 1.00504(6) 0.49381(8) 0.70663(8) 0.0403(3) Uani 1 1 d . . . . .
Zn1 Zn 0.83921(9) 0.58944(11) 0.68062(10) 0.0228(3) Uani 1 1 d . . . . .
Zn2 Zn 0.82525(9) 1.00557(11) 0.33864(10) 0.0234(3) Uani 1 1 d . . . . .
N2 N 0.5988(7) 0.6035(9) 0.7334(7) 0.025(2) Uani 1 1 d . . . . .
N4 N 0.6744(6) 0.2780(9) 0.7764(7) 0.024(2) Uani 1 1 d . . . . .
N8 N 0.7858(7) 0.8198(8) 0.3261(7) 0.023(2) Uani 1 1 d . . . . .
N1 N 0.4629(7) 0.4930(9) 0.7942(7) 0.026(2) Uani 1 1 d . . . . .
N3 N 0.7387(7) 0.4672(9) 0.7264(8) 0.025(2) Uani 1 1 d . . . . .
N5 N 0.8049(7) 0.6056(9) 0.5389(7) 0.029(2) Uani 1 1 d . . . . .
N7 N 0.7343(6) 0.6265(9) 0.2578(8) 0.025(2) Uani 1 1 d . . . . .
N6 N 0.7462(8) 0.4915(9) 0.3990(8) 0.031(2) Uani 1 1 d . . . . .
C5 C 0.7508(10) 0.3373(10) 0.7477(9) 0.029(3) Uani 1 1 d . . . . .
H5 H 0.810095 0.293500 0.742138 0.035 Uiso 1 1 calc R U . . .
C10 C 0.7555(8) 0.7537(11) 0.2453(9) 0.025(2) Uani 1 1 d . . . . .
H10 H 0.750048 0.795137 0.184839 0.030 Uiso 1 1 calc R U . . .
C4 C 0.6439(8) 0.4883(11) 0.7453(8) 0.024(2) Uani 1 1 d . . . . .
C2 C 0.5106(8) 0.3759(11) 0.8028(8) 0.024(2) Uani 1 1 d . . . . .
H2 H 0.480905 0.300284 0.827941 0.029 Uiso 1 1 calc R U . . .
C1 C 0.5100(8) 0.5968(10) 0.7594(10) 0.029(3) Uani 1 1 d . . . . .
H1 H 0.474227 0.675588 0.752794 0.035 Uiso 1 1 calc R U . . .
C6 C 0.7724(9) 0.5005(10) 0.4923(9) 0.029(3) Uani 1 1 d . . . . .
H6 H 0.766929 0.422504 0.528667 0.035 Uiso 1 1 calc R U . . .
C8 C 0.7868(8) 0.7207(10) 0.3961(9) 0.023(2) Uani 1 1 d . . . . .
C9 C 0.7522(8) 0.6062(11) 0.3532(8) 0.023(2) Uani 1 1 d . . . . .
C3 C 0.6031(8) 0.3722(10) 0.7735(8) 0.022(2) Uani 1 1 d . . . . .
C7 C 0.8106(8) 0.7221(11) 0.4889(9) 0.029(3) Uani 1 1 d . . . . .
H7 H 0.830893 0.800841 0.519694 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
I2 Zn2 2.5440(16) . ?
I1 Zn1 2.5378(16) . ?
Zn1 N4 2.025(9) 2_656 ?
Zn1 N3 2.005(10) . ?
Zn1 N5 2.039(10) . ?
Zn2 N8 1.978(8) . ?
Zn2 N1 2.052(10) 4_675 ?
Zn2 N7 1.993(10) 2_655 ?
N2 C4 1.341(14) . ?
N2 C1 1.313(16) . ?
N4 C5 1.308(16) . ?
N4 C3 1.386(14) . ?
N8 C10 1.375(15) . ?
N8 C8 1.410(13) . ?
N1 C2 1.371(14) . ?
N1 C1 1.348(15) . ?
N3 C5 1.366(13) . ?
N3 C4 1.384(15) . ?
N5 C6 1.328(15) . ?
N5 C7 1.383(14) . ?
N7 C10 1.343(14) . ?
N7 C9 1.372(15) . ?
N6 C6 1.352(17) . ?
N6 C9 1.338(15) . ?
C5 H5 0.9500 . ?
C10 H10 0.9500 . ?
C4 C3 1.378(15) . ?
C2 H2 0.9500 . ?
C2 C3 1.377(16) . ?
C1 H1 0.9500 . ?
C6 H6 0.9500 . ?
C8 C9 1.392(15) . ?
C8 C7 1.335(17) . ?
C7 H7 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Zn1 I1 114.6(3) 2_656 . ?
N4 Zn1 N5 101.1(4) 2_656 . ?
N3 Zn1 I1 111.6(3) . . ?
N3 Zn1 N4 114.7(4) . 2_656 ?
N3 Zn1 N5 102.7(4) . . ?
N5 Zn1 I1 110.8(3) . . ?
N8 Zn2 I2 117.3(3) . . ?
N8 Zn2 N1 104.1(4) . 4_675 ?
N8 Zn2 N7 114.9(4) . 2_655 ?
N1 Zn2 I2 108.0(3) 4_675 . ?
N7 Zn2 I2 111.0(3) 2_655 . ?
N7 Zn2 N1 99.5(4) 2_655 4_675 ?
C1 N2 C4 111.6(9) . . ?
C5 N4 Zn1 128.1(8) . 2_646 ?
C5 N4 C3 105.7(9) . . ?
C3 N4 Zn1 126.2(7) . 2_646 ?
C10 N8 Zn2 128.3(8) . . ?
C10 N8 C8 102.8(9) . . ?
C8 N8 Zn2 128.9(7) . . ?
C2 N1 Zn2 116.2(8) . 4_576 ?
C1 N1 Zn2 125.8(7) . 4_576 ?
C1 N1 C2 118.1(10) . . ?
C5 N3 Zn1 126.1(8) . . ?
C5 N3 C4 102.8(10) . . ?
C4 N3 Zn1 131.2(7) . . ?
C6 N5 Zn1 118.8(8) . . ?
C6 N5 C7 117.8(10) . . ?
C7 N5 Zn1 123.4(8) . . ?
C10 N7 Zn2 126.7(9) . 2_645 ?
C10 N7 C9 103.8(10) . . ?
C9 N7 Zn2 129.1(7) . 2_645 ?
C9 N6 C6 112.8(10) . . ?
N4 C5 N3 114.7(11) . . ?
N4 C5 H5 122.6 . . ?
N3 C5 H5 122.6 . . ?
N8 C10 H10 122.3 . . ?
N7 C10 N8 115.4(10) . . ?
N7 C10 H10 122.3 . . ?
N2 C4 N3 124.3(9) . . ?
N2 C4 C3 126.0(11) . . ?
C3 C4 N3 109.6(10) . . ?
N1 C2 H2 121.3 . . ?
N1 C2 C3 117.4(10) . . ?
C3 C2 H2 121.3 . . ?
N2 C1 N1 128.6(10) . . ?
N2 C1 H1 115.7 . . ?
N1 C1 H1 115.7 . . ?
N5 C6 N6 127.6(10) . . ?
N5 C6 H6 116.2 . . ?
N6 C6 H6 116.2 . . ?
C9 C8 N8 107.6(10) . . ?
C7 C8 N8 132.1(10) . . ?
C7 C8 C9 120.3(10) . . ?
N7 C9 C8 110.3(10) . . ?
N6 C9 N7 126.1(10) . . ?
N6 C9 C8 123.4(11) . . ?
C4 C3 N4 107.2(10) . . ?
C2 C3 N4 134.3(11) . . ?
C2 C3 C4 117.9(10) . . ?
N5 C7 H7 121.0 . . ?
C8 C7 N5 118.0(10) . . ?
C8 C7 H7 121.0 . . ?

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
Zn1 N4 C5 N3 -177.7(8) 2_646 . . . ?
Zn1 N4 C3 C4 176.6(8) 2_646 . . . ?
Zn1 N4 C3 C2 6.1(19) 2_646 . . . ?
Zn1 N3 C5 N4 180.0(8) . . . . ?
Zn1 N3 C4 N2 1.4(18) . . . . ?
Zn1 N3 C4 C3 178.7(8) . . . . ?
Zn1 N5 C6 N6 -179.9(10) . . . . ?
Zn1 N5 C7 C8 179.6(9) . . . . ?
Zn2 N8 C10 N7 179.2(8) . . . . ?
Zn2 N8 C8 C9 179.9(8) . . . . ?
Zn2 N8 C8 C7 2(2) . . . . ?
Zn2 N1 C2 C3 -180.0(8) 4_576 . . . ?
Zn2 N1 C1 N2 177.0(10) 4_576 . . . ?
Zn2 N7 C10 N8 172.6(8) 2_645 . . . ?
Zn2 N7 C9 N6 11.0(17) 2_645 . . . ?
Zn2 N7 C9 C8 -174.6(8) 2_645 . . . ?
N2 C4 C3 N4 179.8(11) . . . . ?
N2 C4 C3 C2 -7.8(19) . . . . ?
N8 C8 C9 N7 3.3(13) . . . . ?
N8 C8 C9 N6 178.0(10) . . . . ?
N8 C8 C7 N5 -179.2(12) . . . . ?
N1 C2 C3 N4 175.1(12) . . . . ?
N1 C2 C3 C4 5.3(16) . . . . ?
N3 C4 C3 N4 2.6(14) . . . . ?
N3 C4 C3 C2 174.9(10) . . . . ?
C5 N4 C3 C4 -2.2(13) . . . . ?
C5 N4 C3 C2 -172.7(13) . . . . ?
C5 N3 C4 N2 -179.2(12) . . . . ?
C5 N3 C4 C3 -1.9(13) . . . . ?
C10 N8 C8 C9 -3.3(12) . . . . ?
C10 N8 C8 C7 179.1(13) . . . . ?
C10 N7 C9 N6 -176.3(11) . . . . ?
C10 N7 C9 C8 -1.8(12) . . . . ?
C4 N2 C1 N1 -0.1(19) . . . . ?
C4 N3 C5 N4 0.5(14) . . . . ?
C2 N1 C1 N2 -2(2) . . . . ?
C1 N2 C4 N3 -178.1(12) . . . . ?
C1 N2 C4 C3 5.0(18) . . . . ?
C1 N1 C2 C3 -1.1(16) . . . . ?
C6 N5 C7 C8 -2.6(17) . . . . ?
C6 N6 C9 N7 177.1(11) . . . . ?
C6 N6 C9 C8 3.3(17) . . . . ?
C8 N8 C10 N7 2.4(13) . . . . ?
C9 N7 C10 N8 -0.4(13) . . . . ?
C9 N6 C6 N5 -2.5(19) . . . . ?
C9 C8 C7 N5 3.5(18) . . . . ?
C3 N4 C5 N3 1.1(14) . . . . ?
C7 N5 C6 N6 2.3(19) . . . . ?
C7 C8 C9 N7 -178.8(11) . . . . ?
C7 C8 C9 N6 -4.1(18) . . . . ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_platon_squeeze_details          ?
_platon_squeeze_special_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 0.000 -0.021 0.000 252 71 ' '
2 0.500 -0.015 0.500 252 71 ' '
3 0.475 0.147 -0.004 11 0 ' '
4 0.975 0.353 0.496 11 0 ' '
5 0.025 0.647 0.504 11 0 ' '
6 0.525 0.853 0.004 11 0 ' '

_platon_squeeze_void_probe_radius 1.20
_olex2_exptl_crystal_mounting_method 'glass fiber in paratone oil'
_olex2_submission_special_instructions 'No special instructions were received'

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;
