# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_20180117_2a_0m_pl
_database_code_depnum_ccdc_archive 'CCDC 1958977'
loop_
_audit_author_name
_audit_author_address
'Hai-Dong Lv'
;College of Chemistry, Liaoning University
China
;
_audit_update_record             
;
2019-10-12 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;
_audit_creation_date             2018-07-12
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H22 N4, 2(Cl4 Cu)'
_chemical_formula_sum            'C14 H22 Cl8 Cu2 N4'
_chemical_formula_weight         657.03
_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'
Cu Cu 0.3201 1.2651 '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      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                   7.552(3)
_cell_length_b                   22.128(8)
_cell_length_c                   7.398(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.831(11)
_cell_angle_gamma                90
_cell_volume                     1235.7(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9035
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.943
_cell_measurement_theta_min      3.268
_shelx_estimated_absorpt_T_max   0.839
_shelx_estimated_absorpt_T_min   0.599
_exptl_absorpt_coefficient_mu    2.596
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.2925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1541 before and 0.0865 after correction.
The Ratio of minimum to maximum transmission is 0.3923.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.766
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13657
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         27.954
_diffrn_reflns_theta_min         3.267
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'CCD Areadetetor'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2668
_reflns_number_total             2865
_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 v8.37A (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    ?
_refine_diff_density_max         1.067
_refine_diff_density_min         -1.072
_refine_diff_density_rms         0.151
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.231
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2865
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0669
_refine_ls_restrained_S_all      1.231
_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)+(0.0516P)²+5.5498P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1644
_refine_ls_wR_factor_ref         0.1673
_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, All N(H,H) groups
2.a Riding coordinates:
 N1(H1A,H1B)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1C,H1D), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C7(H7), C4(H4), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.1778(5) 0.03873(17) 0.8705(5) 0.0224(7) Uani 1 1 d . . . . .
H1A H 0.2294 0.0045 0.8377 0.027 Uiso 1 1 d R . . . .
H1B H 0.2403 0.0537 0.9643 0.027 Uiso 1 1 d R . . . .
N2 N 0.1732(6) 0.24504(19) 0.8533(6) 0.0338(9) Uani 1 1 d . . . . .
H2 H 0.2489 0.2725 0.8840 0.041 Uiso 1 1 calc R . . . .
C3 C 0.1141(6) 0.1441(2) 0.7659(6) 0.0224(8) Uani 1 1 d . . . . .
C1 C -0.0041(6) 0.02481(19) 0.9291(6) 0.0230(9) Uani 1 1 d . . . . .
H1C H -0.0770 0.0118 0.8260 0.028 Uiso 1 1 calc R . . . .
H1D H -0.0572 0.0608 0.9792 0.028 Uiso 1 1 calc R . . . .
C2 C 0.1835(7) 0.0832(2) 0.7149(6) 0.0267(9) Uani 1 1 d . . . . .
H2A H 0.3047 0.0872 0.6770 0.032 Uiso 1 1 calc R . . . .
H2B H 0.1132 0.0675 0.6133 0.032 Uiso 1 1 calc R . . . .
C7 C 0.2321(6) 0.1893(2) 0.8205(7) 0.0294(10) Uani 1 1 d . . . . .
H7 H 0.3523 0.1808 0.8343 0.035 Uiso 1 1 calc R . . . .
C4 C -0.0628(6) 0.1587(2) 0.7520(6) 0.0278(9) Uani 1 1 d . . . . .
H4 H -0.1443 0.1294 0.7148 0.033 Uiso 1 1 calc R . . . .
C5 C -0.1225(7) 0.2168(2) 0.7928(7) 0.0325(10) Uani 1 1 d . . . . .
H5 H -0.2428 0.2259 0.7879 0.039 Uiso 1 1 calc R . . . .
C6 C 0.0011(8) 0.2599(2) 0.8403(7) 0.0351(11) Uani 1 1 d . . . . .
H6 H -0.0344 0.2994 0.8633 0.042 Uiso 1 1 calc R . . . .
Cu1 Cu 0.52617(8) 0.11339(3) 0.28227(8) 0.0282(2) Uani 1 1 d . . . . .
Cl2 Cl 0.22828(15) 0.11113(6) 0.24882(17) 0.0328(3) Uani 1 1 d . . . . .
Cl1 Cl 0.53214(16) 0.19268(6) 0.47564(19) 0.0359(3) Uani 1 1 d . . . . .
Cl3 Cl 0.57836(17) 0.08739(8) -0.00535(18) 0.0416(4) Uani 1 1 d . . . . .
Cl4 Cl 0.7593(3) 0.06481(9) 0.4090(3) 0.0698(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 H1A 0.8898 . ?
N1 H1B 0.8903 . ?
N1 C1 1.486(5) . ?
N1 C2 1.516(6) . ?
N2 H2 0.8600 . ?
N2 C7 1.335(7) . ?
N2 C6 1.341(8) . ?
C3 C2 1.500(7) . ?
C3 C7 1.391(6) . ?
C3 C4 1.375(7) . ?
C1 C1 1.518(8) 3_557 ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C7 H7 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.397(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.374(7) . ?
C6 H6 0.9300 . ?
Cu1 Cl2 2.2559(15) . ?
Cu1 Cl1 2.2633(14) . ?
Cu1 Cl3 2.2511(16) . ?
Cu1 Cl4 2.2426(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A N1 H1B 107.7 . . ?
C1 N1 H1A 108.7 . . ?
C1 N1 H1B 108.8 . . ?
C1 N1 C2 113.9(3) . . ?
C2 N1 H1A 108.8 . . ?
C2 N1 H1B 108.8 . . ?
C7 N2 H2 118.6 . . ?
C7 N2 C6 122.8(4) . . ?
C6 N2 H2 118.6 . . ?
C7 C3 C2 119.7(4) . . ?
C4 C3 C2 122.6(4) . . ?
C4 C3 C7 117.7(4) . . ?
N1 C1 C1 109.5(4) . 3_557 ?
N1 C1 H1C 109.8 . . ?
N1 C1 H1D 109.8 . . ?
C1 C1 H1C 109.8 3_557 . ?
C1 C1 H1D 109.8 3_557 . ?
H1C C1 H1D 108.2 . . ?
N1 C2 H2A 109.2 . . ?
N1 C2 H2B 109.2 . . ?
C3 C2 N1 111.9(4) . . ?
C3 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
N2 C7 C3 120.2(5) . . ?
N2 C7 H7 119.9 . . ?
C3 C7 H7 119.9 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.3(4) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.9 . . ?
C6 C5 C4 118.2(5) . . ?
C6 C5 H5 120.9 . . ?
N2 C6 C5 119.7(5) . . ?
N2 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
Cl2 Cu1 Cl1 94.94(5) . . ?
Cl3 Cu1 Cl2 95.44(5) . . ?
Cl3 Cu1 Cl1 142.65(7) . . ?
Cl4 Cu1 Cl2 143.34(8) . . ?
Cl4 Cu1 Cl1 96.19(6) . . ?
Cl4 Cu1 Cl3 96.53(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C4 C5 C6 2.6(8) . . . . ?
C1 N1 C2 C3 64.0(5) . . . . ?
C2 N1 C1 C1 174.0(4) . . . 3_557 ?
C2 C3 C7 N2 175.0(4) . . . . ?
C2 C3 C4 C5 -177.0(4) . . . . ?
C7 N2 C6 C5 0.5(8) . . . . ?
C7 C3 C2 N1 96.7(5) . . . . ?
C7 C3 C4 C5 -0.5(7) . . . . ?
C4 C3 C2 N1 -86.9(5) . . . . ?
C4 C3 C7 N2 -1.6(7) . . . . ?
C4 C5 C6 N2 -2.6(8) . . . . ?
C6 N2 C7 C3 1.7(8) . . . . ?

_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_20181223_1a_0m
_database_code_depnum_ccdc_archive 'CCDC 1958981'
loop_
_audit_author_name
_audit_author_address
'Hai-Dong Lv'
;College of Chemistry, Liaoning University
China
;
_audit_update_record             
;
2019-10-12 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;
_audit_creation_date             2019-03-06
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H20 I6 N4 Zn2, 2(C H4 O)'
_chemical_formula_sum            'C16 H28 I6 N4 O2 Zn2'
_chemical_formula_weight         1200.56
_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'
Zn Zn 0.2839 1.4301 '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                   7.9785(5)
_cell_length_b                   10.7150(7)
_cell_length_c                   10.8206(7)
_cell_angle_alpha                63.205(2)
_cell_angle_beta                 73.580(2)
_cell_angle_gamma                87.892(2)
_cell_volume                     787.59(9)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.333
_cell_measurement_theta_min      3.247
_shelx_estimated_absorpt_T_max   0.588
_shelx_estimated_absorpt_T_min   0.496
_exptl_absorpt_coefficient_mu    7.421
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.2964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1498 before and 0.0591 after correction.
The Ratio of minimum to maximum transmission is 0.3975.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.531
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             546
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.950
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12358
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         28.333
_diffrn_reflns_theta_min         3.247
_diffrn_ambient_temperature      296.16
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3493
_reflns_number_total             3767
_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 v8.37A (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 (Sheldrick, 2015)'
_refine_diff_density_max         1.444
_refine_diff_density_min         -1.459
_refine_diff_density_rms         0.154
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         3767
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0360
_refine_ls_restrained_S_all      1.183
_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)+(0.0180P)²+3.1647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0859
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1C,H1D), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4), C6(H6), C5(H5)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_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 0.67486(4) 0.38461(3) 0.36312(3) 0.03461(10) Uani 1 1 d . . . . .
I1 I 0.99542(5) 0.73493(4) -0.02689(3) 0.04306(11) Uani 1 1 d . . . . .
I3 I 0.46587(5) 0.77343(4) 0.16596(4) 0.04807(11) Uani 1 1 d . . . . .
Zn04 Zn 0.74626(8) 0.65653(6) 0.21382(5) 0.03272(13) Uani 1 1 d . . . . .
N1 N 0.6486(5) 0.5925(4) 0.8090(4) 0.0276(7) Uani 1 1 d . . . . .
H1A H 0.574(7) 0.587(6) 0.760(6) 0.033 Uiso 1 1 d R . . . .
N2 N 0.8400(5) 0.7168(4) 0.3411(4) 0.0304(8) Uani 1 1 d . . . . .
C3 C 0.8674(5) 0.6762(5) 0.5705(4) 0.0262(8) Uani 1 1 d . . . . .
C7 C 0.8136(6) 0.6341(5) 0.4830(4) 0.0275(8) Uani 1 1 d . . . . .
H7 H 0.7564 0.5441 0.5247 0.033 Uiso 1 1 calc R . . . .
C1 C 0.5958(6) 0.4958(5) 0.9672(4) 0.0294(9) Uani 1 1 d . . . . .
H1C H 0.6672 0.5221 1.0127 0.035 Uiso 1 1 calc R . . . .
H1D H 0.6139 0.4002 0.9836 0.035 Uiso 1 1 calc R . . . .
C2 C 0.8296(6) 0.5799(5) 0.7289(4) 0.0305(9) Uani 1 1 d . . . . .
H2A H 0.9150 0.6039 0.7653 0.037 Uiso 1 1 calc R . . . .
H2B H 0.8390 0.4837 0.7447 0.037 Uiso 1 1 calc R . . . .
C4 C 0.9538(7) 0.8098(5) 0.5060(5) 0.0368(10) Uani 1 1 d . . . . .
H4 H 0.9910 0.8422 0.5614 0.044 Uiso 1 1 calc R . . . .
C6 C 0.9236(8) 0.8451(5) 0.2808(5) 0.0435(12) Uani 1 1 d . . . . .
H6 H 0.9414 0.9032 0.1824 0.052 Uiso 1 1 calc R . . . .
C5 C 0.9849(9) 0.8947(6) 0.3596(6) 0.0491(14) Uani 1 1 d . . . . .
H5 H 1.0459 0.9837 0.3146 0.059 Uiso 1 1 calc R . . . .
O1 O 0.6235(8) 0.8614(5) 0.7764(5) 0.0619(12) Uani 1 1 d . . . . .
H1 H 0.6012 0.8687 0.8515 0.093 Uiso 1 1 calc GR . . . .
C8 C 0.5194(16) 0.9462(9) 0.6909(13) 0.095(3) Uani 1 1 d . . . . .
H8A H 0.5614 0.9527 0.5956 0.142 Uiso 1 1 calc GR . . . .
H8B H 0.5267 1.0385 0.6838 0.142 Uiso 1 1 calc GR . . . .
H8C H 0.3994 0.9051 0.7350 0.142 Uiso 1 1 calc GR . . . .
H1B H 0.646(8) 0.675(7) 0.792(7) 0.037(16) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I2 Zn04 2.6042(6) . ?
I1 Zn04 2.5816(6) . ?
I3 Zn04 2.5895(7) . ?
Zn04 N2 2.072(4) . ?
N1 H1A 0.92(6) . ?
N1 C1 1.485(5) . ?
N1 C2 1.496(6) . ?
N1 H1B 0.82(6) . ?
N2 C7 1.338(5) . ?
N2 C6 1.331(6) . ?
C3 C7 1.384(6) . ?
C3 C2 1.493(6) . ?
C3 C4 1.382(6) . ?
C7 H7 0.9300 . ?
C1 C1 1.511(9) 2_667 ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C4 H4 0.9300 . ?
C4 C5 1.376(7) . ?
C6 H6 0.9300 . ?
C6 C5 1.383(7) . ?
C5 H5 0.9300 . ?
O1 H1 0.8200 . ?
O1 C8 1.411(10) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I1 Zn04 I2 113.29(2) . . ?
I1 Zn04 I3 110.44(2) . . ?
I3 Zn04 I2 110.34(2) . . ?
N2 Zn04 I2 104.99(11) . . ?
N2 Zn04 I1 106.29(11) . . ?
N2 Zn04 I3 111.31(12) . . ?
H1A N1 H1B 100(5) . . ?
C1 N1 H1A 116(3) . . ?
C1 N1 C2 113.9(4) . . ?
C1 N1 H1B 112(4) . . ?
C2 N1 H1A 107(3) . . ?
C2 N1 H1B 106(4) . . ?
C7 N2 Zn04 122.6(3) . . ?
C6 N2 Zn04 118.7(3) . . ?
C6 N2 C7 118.6(4) . . ?
C7 C3 C2 120.3(4) . . ?
C4 C3 C7 117.5(4) . . ?
C4 C3 C2 122.2(4) . . ?
N2 C7 C3 123.0(4) . . ?
N2 C7 H7 118.5 . . ?
C3 C7 H7 118.5 . . ?
N1 C1 C1 109.1(4) . 2_667 ?
N1 C1 H1C 109.9 . . ?
N1 C1 H1D 109.9 . . ?
C1 C1 H1C 109.9 2_667 . ?
C1 C1 H1D 109.9 2_667 . ?
H1C C1 H1D 108.3 . . ?
N1 C2 H2A 109.7 . . ?
N1 C2 H2B 109.7 . . ?
C3 C2 N1 110.0(4) . . ?
C3 C2 H2A 109.7 . . ?
C3 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(4) . . ?
C5 C4 H4 120.0 . . ?
N2 C6 H6 118.9 . . ?
N2 C6 C5 122.2(4) . . ?
C5 C6 H6 118.9 . . ?
C4 C5 C6 118.7(5) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C8 O1 H1 109.5 . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_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_20180713_1a_0m
_database_code_depnum_ccdc_archive 'CCDC 1958984'
loop_
_audit_author_name
_audit_author_address
'Hai-Dong Lv'
;College of Chemistry, Liaoning University
China
;
_audit_update_record             
;
2020-02-23 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;
_audit_creation_date             2020-02-22
_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         'C14 H20 Br6 N4 Zn2, 2(H2 O)'
_chemical_formula_sum            'C14 H24 Br6 N4 O2 Zn2'
_chemical_formula_weight         890.57
_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'
Br Br -0.2901 2.4595 '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'
Zn Zn 0.2839 1.4301 '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                   7.458(5)
_cell_length_b                   9.586(6)
_cell_length_c                   9.603(6)
_cell_angle_alpha                99.830(18)
_cell_angle_beta                 95.106(18)
_cell_angle_gamma                103.695(19)
_cell_volume                     651.2(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3317
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.409
_cell_measurement_theta_min      3.127
_shelx_estimated_absorpt_T_max   0.511
_shelx_estimated_absorpt_T_min   0.404
_exptl_absorpt_coefficient_mu    11.063
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.2588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1633 before and 0.0707 after correction. The Ratio of minimum to maximum transmission is 0.3471. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.271
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             422
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.0851
_diffrn_reflns_Laue_measured_fraction_full 0.861
_diffrn_reflns_Laue_measured_fraction_max 0.862
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3741
_diffrn_reflns_point_group_measured_fraction_full 0.861
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         25.488
_diffrn_reflns_theta_min         2.231
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.861
_diffrn_measured_fraction_theta_max 0.862
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1748
_reflns_number_total             2087
_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 v8.37A (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 (Sheldrick, 2015)'
_refine_diff_density_max         1.648
_refine_diff_density_min         -1.916
_refine_diff_density_rms         0.538
_refine_ls_extinction_coef       0.173(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         2087
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0966
_refine_ls_restrained_S_all      1.196
_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)+(0.1417P)²+3.7471P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2295
_refine_ls_wR_factor_ref         0.2491
_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,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 H1A-H1E
 2.2 with sigma of 0.02
3.a Free rotating group:
 O1(H1E,H1F)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), N1(H1A,H1B), C1(H1C,H1D)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C5(H5), C4(H4)
;
_atom_sites_solution_hydrogens   mixed
_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
Zn1 Zn 0.61311(18) 0.77227(17) 0.71068(14) 0.0357(6) Uani 1 1 d . . . . .
Br3 Br 0.47869(16) 0.75826(19) 0.47142(14) 0.0515(6) Uani 1 1 d . . . . .
Br2 Br 0.87736(18) 0.6726(2) 0.70968(17) 0.0537(6) Uani 1 1 d . . . . .
Br1 Br 0.6963(3) 1.01662(18) 0.84775(16) 0.0624(7) Uani 1 1 d . . . . .
N2 N 0.4166(12) 0.6440(11) 0.8024(10) 0.030(2) Uani 1 1 d . . . . .
C3 C 0.1628(14) 0.4281(12) 0.7766(12) 0.028(2) Uani 1 1 d . . . . .
C7 C 0.2861(14) 0.5305(15) 0.7205(13) 0.033(3) Uani 1 1 d . . . . .
H7 H 0.278081 0.520188 0.621855 0.039 Uiso 1 1 calc R . . . .
C2 C 0.0170(15) 0.3071(14) 0.6779(14) 0.036(3) Uani 1 1 d . . . . .
H2A H -0.086618 0.273283 0.728601 0.043 Uiso 1 1 calc R . . . .
H2B H -0.029522 0.344559 0.598261 0.043 Uiso 1 1 calc R . . . .
N1 N 0.0942(12) 0.1827(11) 0.6237(11) 0.032(2) Uani 1 1 d . . . . .
H1A H 0.135211 0.147927 0.697120 0.038 Uiso 1 1 calc DR . . . .
H1B H 0.191085 0.214764 0.579342 0.038 Uiso 1 1 calc R . . . .
O1 O 0.239(2) 0.050(2) 0.8154(17) 0.100(5) Uani 1 1 d . . . . .
H1E H 0.153113 0.019178 0.863970 0.150 Uiso 1 1 d DG . . . .
H1F H 0.327536 0.014921 0.842425 0.150 Uiso 1 1 d G . . . .
C1 C -0.0450(15) 0.0612(14) 0.5230(12) 0.034(3) Uani 1 1 d . . . . .
H1C H -0.087134 0.096582 0.440322 0.040 Uiso 1 1 calc R . . . .
H1D H -0.152194 0.025879 0.569544 0.040 Uiso 1 1 calc R . . . .
C6 C 0.4208(16) 0.6613(15) 0.9434(13) 0.037(3) Uani 1 1 d . . . . .
H6 H 0.505980 0.742009 1.000816 0.044 Uiso 1 1 calc R . . . .
C5 C 0.3047(17) 0.5651(13) 1.0082(11) 0.033(3) Uani 1 1 d . . . . .
H5 H 0.313184 0.580109 1.107081 0.040 Uiso 1 1 calc R . . . .
C4 C 0.1750(17) 0.4456(17) 0.9236(14) 0.042(3) Uani 1 1 d . . . . .
H4 H 0.097226 0.378195 0.965153 0.051 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
Zn1 Br3 2.392(2) . ?
Zn1 Br2 2.385(2) . ?
Zn1 Br1 2.391(2) . ?
Zn1 N2 2.045(10) . ?
N2 C7 1.349(15) . ?
N2 C6 1.333(15) . ?
C3 C7 1.394(16) . ?
C3 C2 1.507(15) . ?
C3 C4 1.386(17) . ?
C7 H7 0.9300 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 N1 1.480(16) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 C1 1.494(13) . ?
O1 H1E 0.8503 . ?
O1 H1F 0.8499 . ?
C1 C1 1.51(3) 2_556 ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C6 H6 0.9300 . ?
C6 C5 1.378(18) . ?
C5 H5 0.9300 . ?
C5 C4 1.387(19) . ?
C4 H4 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
Br2 Zn1 Br3 110.12(8) . . ?
Br2 Zn1 Br1 110.45(9) . . ?
Br1 Zn1 Br3 112.53(9) . . ?
N2 Zn1 Br3 106.8(3) . . ?
N2 Zn1 Br2 107.8(3) . . ?
N2 Zn1 Br1 109.0(3) . . ?
C7 N2 Zn1 120.1(8) . . ?
C6 N2 Zn1 122.0(8) . . ?
C6 N2 C7 117.8(10) . . ?
C7 C3 C2 119.9(10) . . ?
C4 C3 C7 117.9(11) . . ?
C4 C3 C2 122.2(11) . . ?
N2 C7 C3 123.1(10) . . ?
N2 C7 H7 118.5 . . ?
C3 C7 H7 118.5 . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N1 C2 C3 111.1(9) . . ?
N1 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
C2 N1 H1A 109.0 . . ?
C2 N1 H1B 109.0 . . ?
C2 N1 C1 112.9(9) . . ?
H1A N1 H1B 107.8 . . ?
C1 N1 H1A 109.0 . . ?
C1 N1 H1B 109.0 . . ?
H1E O1 H1F 104.5 . . ?
N1 C1 C1 108.8(11) . 2_556 ?
N1 C1 H1C 109.9 . . ?
N1 C1 H1D 109.9 . . ?
C1 C1 H1C 109.9 2_556 . ?
C1 C1 H1D 109.9 2_556 . ?
H1C C1 H1D 108.3 . . ?
N2 C6 H6 118.5 . . ?
N2 C6 C5 123.0(11) . . ?
C5 C6 H6 118.5 . . ?
C6 C5 H5 120.5 . . ?
C6 C5 C4 119.0(10) . . ?
C4 C5 H5 120.5 . . ?
C3 C4 C5 119.2(12) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 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
Zn1 N2 C7 C3 171.8(9) . . . . ?
Zn1 N2 C6 C5 -171.5(9) . . . . ?
N2 C6 C5 C4 -1(2) . . . . ?
C3 C2 N1 C1 -178.9(9) . . . . ?
C7 N2 C6 C5 3.2(18) . . . . ?
C7 C3 C2 N1 83.7(14) . . . . ?
C7 C3 C4 C5 1.6(18) . . . . ?
C2 C3 C7 N2 178.1(11) . . . . ?
C2 C3 C4 C5 -175.7(11) . . . . ?
C2 N1 C1 C1 -178.5(11) . . . 2_556 ?
C6 N2 C7 C3 -3.1(18) . . . . ?
C6 C5 C4 C3 -1.5(19) . . . . ?
C4 C3 C7 N2 0.7(18) . . . . ?
C4 C3 C2 N1 -99.0(13) . . . . ?

_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_20190118_1a_0m
_database_code_depnum_ccdc_archive 'CCDC 1958982'
loop_
_audit_author_name
_audit_author_address
'Hai-Dong Lv'
;College of Chemistry, Liaoning University
China
;
_audit_update_record             
;
2019-10-12 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;
_audit_creation_date             2019-03-06
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H20 I6 N4 Zn2, 2(H2 O)'
_chemical_formula_sum            'C14 H24 I6 N4 O2 Zn2'
_chemical_formula_weight         1172.51
_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'
Zn Zn 0.2839 1.4301 '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                   7.7826(18)
_cell_length_b                   9.850(2)
_cell_length_c                   10.106(2)
_cell_angle_alpha                101.146(6)
_cell_angle_beta                 94.713(6)
_cell_angle_gamma                105.848(6)
_cell_volume                     723.7(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.364
_cell_measurement_theta_min      2.974
_shelx_estimated_absorpt_T_max   0.602
_shelx_estimated_absorpt_T_min   0.499
_exptl_absorpt_coefficient_mu    8.073
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.1297
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1762 before and 0.0921 after correction.
The Ratio of minimum to maximum transmission is 0.1739.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.690
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             530
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13372
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.973
_diffrn_ambient_temperature      296.16
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2386
_reflns_number_total             2478
_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 v8.37A (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 (Sheldrick, 2015)'
_refine_diff_density_max         1.818
_refine_diff_density_min         -2.684
_refine_diff_density_rms         0.424
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         2478
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0656
_refine_ls_restrained_S_all      1.130
_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)+(0.1216P)²+11.4311P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1968
_refine_ls_wR_factor_ref         0.1989
_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,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 H1F-H1B
 2.45 with sigma of 0.01
 H1E-H1B
 2.3 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(N2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Free rotating group:
 O1(H1E,H1F)
4.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C2(H2A,H2B), C1(H1C,H1D)
4.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_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 0.53330(10) 0.24028(10) 0.52197(9) 0.0416(3) Uani 1 1 d . . . . .
I2 I 0.10387(11) 0.32636(10) 0.28544(9) 0.0423(3) Uani 1 1 d . . . . .
I3 I 0.28321(14) -0.03133(8) 0.13095(9) 0.0483(4) Uani 1 1 d . . . . .
Zn1 Zn 0.38159(17) 0.23021(13) 0.27985(13) 0.0291(4) Uani 1 1 d . . . . .
N2 N 0.5761(12) 0.3627(8) 0.1966(9) 0.0223(17) Uani 1 1 d . U . . .
N1 N 0.9029(12) 0.8179(9) 0.3793(9) 0.0254(18) Uani 1 1 d . . . . .
H1A H 0.8118 0.7864 0.4242 0.030 Uiso 1 1 calc R . . . .
H1B H 0.8599 0.8486 0.3100 0.030 Uiso 1 1 calc DR . . . .
C3 C 0.8279(13) 0.5749(10) 0.2269(11) 0.022(2) Uani 1 1 d . . . . .
O1 O 0.749(2) 0.9330(15) 0.1980(13) 0.079(4) Uani 1 1 d . . . . .
H1E H 0.8104 0.9606 0.1372 0.118 Uiso 1 1 d DG . . . .
H1F H 0.6373 0.9147 0.1698 0.118 Uiso 1 1 d DG . . . .
C7 C 0.7044(14) 0.4774(11) 0.2775(11) 0.023(2) Uani 1 1 d . . . . .
H7 H 0.7089 0.4904 0.3715 0.028 Uiso 1 1 calc R . . . .
C6 C 0.5707(16) 0.3470(12) 0.0613(12) 0.030(2) Uani 1 1 d . . . . .
H6 H 0.4810 0.2701 0.0048 0.036 Uiso 1 1 calc R . . . .
C4 C 0.8219(17) 0.5545(13) 0.0862(13) 0.035(3) Uani 1 1 d . . . . .
H4 H 0.9054 0.6182 0.0492 0.042 Uiso 1 1 calc R . . . .
C2 C 0.9727(15) 0.6952(11) 0.3244(12) 0.029(2) Uani 1 1 d . . . . .
H2A H 1.0148 0.6582 0.3992 0.035 Uiso 1 1 calc R . . . .
H2B H 1.0744 0.7293 0.2776 0.035 Uiso 1 1 calc R . . . .
C5 C 0.6905(18) 0.4382(13) 0.0018(12) 0.037(3) Uani 1 1 d . . . . .
H5 H 0.6838 0.4226 -0.0925 0.044 Uiso 1 1 calc R . . . .
C1 C 1.0442(14) 0.9434(12) 0.4733(11) 0.030(2) Uani 1 1 d . . . . .
H1C H 1.0948 0.9113 0.5482 0.036 Uiso 1 1 calc R . . . .
H1D H 1.1409 0.9831 0.4243 0.036 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 Zn1 2.5998(16) . ?
I2 Zn1 2.5863(16) . ?
I3 Zn1 2.5926(15) . ?
Zn1 N2 2.063(9) . ?
N2 C7 1.355(14) . ?
N2 C6 1.342(15) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 C2 1.488(14) . ?
N1 C1 1.507(13) . ?
C3 C7 1.369(14) . ?
C3 C4 1.392(16) . ?
C3 C2 1.511(14) . ?
O1 H1E 0.8503 . ?
O1 H1F 0.8503 . ?
C7 H7 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.372(17) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(18) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C5 H5 0.9300 . ?
C1 C1 1.50(2) 2_776 ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?

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
I2 Zn1 I1 112.63(6) . . ?
I2 Zn1 I3 108.72(6) . . ?
I3 Zn1 I1 111.25(6) . . ?
N2 Zn1 I1 105.4(3) . . ?
N2 Zn1 I2 108.8(2) . . ?
N2 Zn1 I3 109.9(2) . . ?
C7 N2 Zn1 120.5(7) . . ?
C6 N2 Zn1 121.6(7) . . ?
C6 N2 C7 117.6(9) . . ?
H1A N1 H1B 107.8 . . ?
C2 N1 H1A 108.9 . . ?
C2 N1 H1B 108.9 . . ?
C2 N1 C1 113.1(9) . . ?
C1 N1 H1A 108.9 . . ?
C1 N1 H1B 108.9 . . ?
C7 C3 C4 118.5(10) . . ?
C7 C3 C2 119.3(10) . . ?
C4 C3 C2 122.0(10) . . ?
H1E O1 H1F 109.4 . . ?
N2 C7 C3 122.8(10) . . ?
N2 C7 H7 118.6 . . ?
C3 C7 H7 118.6 . . ?
N2 C6 H6 118.3 . . ?
N2 C6 C5 123.5(10) . . ?
C5 C6 H6 118.3 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.5(11) . . ?
C5 C4 H4 120.3 . . ?
N1 C2 C3 111.0(9) . . ?
N1 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C6 C5 C4 118.1(11) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
N1 C1 H1C 110.1 . . ?
N1 C1 H1D 110.1 . . ?
C1 C1 N1 108.1(11) 2_776 . ?
C1 C1 H1C 110.1 2_776 . ?
C1 C1 H1D 110.1 2_776 . ?
H1C C1 H1D 108.4 . . ?

_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_20180527_1b_0m
_database_code_depnum_ccdc_archive 'CCDC 1958980'
loop_
_audit_author_name
_audit_author_address
'Hai-Dong Lv'
;College of Chemistry, Liaoning University
China
;
_audit_update_record             
;
2019-10-12 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;
_audit_creation_date             2019-01-09
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Cl4 Zn), C14 H22 N4, 2(H2 O)'
_chemical_formula_sum            'C14 H26 Cl8 N4 O2 Zn2'
_chemical_formula_weight         696.73
_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'
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'
Zn Zn 0.2839 1.4301 '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                   12.2223(6)
_cell_length_b                   8.3549(4)
_cell_length_c                   13.5644(7)
_cell_angle_alpha                90
_cell_angle_beta                 105.261(2)
_cell_angle_gamma                90
_cell_volume                     1336.30(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9406
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.328
_cell_measurement_theta_min      3.114
_shelx_estimated_absorpt_T_max   0.818
_shelx_estimated_absorpt_T_min   0.711
_exptl_absorpt_coefficient_mu    2.614
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4291
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1572 before and 0.0798 after correction.
The Ratio of minimum to maximum transmission is 0.5754.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             700
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19659
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         28.328
_diffrn_reflns_theta_min         3.114
_diffrn_ambient_temperature      295.07
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3055
_reflns_number_total             3294
_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 v8.37A (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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.575
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         3294
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.102
_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)+(0.0399P)²+1.9652P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0968
_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, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O1(H1E,H1F)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C1(H1C,H1D), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C7(H7), C4(H4), C6(H6), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
Zn1 Zn 0.24127(2) 0.16363(4) 0.23212(2) 0.02782(11) Uani 1 1 d . . . . .
Cl2 Cl 0.19755(6) 0.22557(9) 0.38094(5) 0.03731(16) Uani 1 1 d . . . . .
Cl1 Cl 0.30103(7) 0.39716(8) 0.17406(5) 0.03829(17) Uani 1 1 d . . . . .
Cl3 Cl 0.07768(6) 0.08928(9) 0.11846(6) 0.04087(17) Uani 1 1 d . . . . .
Cl4 Cl 0.37553(7) -0.02384(9) 0.25139(6) 0.04510(19) Uani 1 1 d . . . . .
N1 N 0.13223(18) 0.8974(3) 0.48517(18) 0.0290(4) Uani 1 1 d . . . . .
H1A H 0.1774 0.9827 0.4935 0.035 Uiso 1 1 calc R . . . .
H1B H 0.1062 0.8795 0.4184 0.035 Uiso 1 1 calc R . . . .
O1 O 0.0686(3) 0.8192(4) 0.2796(2) 0.0685(9) Uani 1 1 d . . . . .
H1E H 0.0106 0.7606 0.2570 0.103 Uiso 1 1 d G . . . .
H1F H 0.0614 0.8944 0.2362 0.103 Uiso 1 1 d G . . . .
N2 N 0.3831(3) 0.6057(3) 0.3748(2) 0.0502(7) Uani 1 1 d . . . . .
H2 H 0.3762 0.5438 0.3229 0.060 Uiso 1 1 calc R . . . .
C3 C 0.3008(2) 0.7277(3) 0.4936(2) 0.0280(5) Uani 1 1 d . . . . .
C1 C 0.0351(2) 0.9315(3) 0.5291(2) 0.0304(5) Uani 1 1 d . . . . .
H1C H 0.0632 0.9599 0.6006 0.036 Uiso 1 1 calc R . . . .
H1D H -0.0118 0.8367 0.5244 0.036 Uiso 1 1 calc R . . . .
C7 C 0.4051(2) 0.7955(3) 0.5392(2) 0.0339(5) Uani 1 1 d . . . . .
H7 H 0.4136 0.8595 0.5968 0.041 Uiso 1 1 calc R . . . .
C2 C 0.1994(2) 0.7555(3) 0.5345(2) 0.0338(5) Uani 1 1 d . . . . .
H2A H 0.1514 0.6612 0.5222 0.041 Uiso 1 1 calc R . . . .
H2B H 0.2245 0.7724 0.6077 0.041 Uiso 1 1 calc R . . . .
C4 C 0.2923(3) 0.6303(3) 0.4099(2) 0.0406(6) Uani 1 1 d . . . . .
H4 H 0.2235 0.5819 0.3781 0.049 Uiso 1 1 calc R . . . .
C6 C 0.4971(3) 0.7686(4) 0.4993(3) 0.0462(7) Uani 1 1 d . . . . .
H6 H 0.5669 0.8159 0.5291 0.055 Uiso 1 1 calc R . . . .
C5 C 0.4842(3) 0.6723(4) 0.4163(3) 0.0517(9) Uani 1 1 d . . . . .
H5 H 0.5450 0.6530 0.3887 0.062 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
Zn1 Cl2 2.2794(7) . ?
Zn1 Cl1 2.2943(7) . ?
Zn1 Cl3 2.2667(7) . ?
Zn1 Cl4 2.2335(8) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 C1 1.489(3) . ?
N1 C2 1.496(3) . ?
O1 H1E 0.8500 . ?
O1 H1F 0.8500 . ?
N2 H2 0.8600 . ?
N2 C4 1.334(5) . ?
N2 C5 1.337(5) . ?
C3 C7 1.383(4) . ?
C3 C2 1.504(4) . ?
C3 C4 1.377(4) . ?
C1 C1 1.521(5) 3_576 ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C7 H7 0.9300 . ?
C7 C6 1.389(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C4 H4 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.358(5) . ?
C5 H5 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
Cl2 Zn1 Cl1 106.32(3) . . ?
Cl3 Zn1 Cl2 107.11(3) . . ?
Cl3 Zn1 Cl1 107.64(3) . . ?
Cl4 Zn1 Cl2 113.07(3) . . ?
Cl4 Zn1 Cl1 110.25(3) . . ?
Cl4 Zn1 Cl3 112.14(3) . . ?
H1A N1 H1B 107.9 . . ?
C1 N1 H1A 109.2 . . ?
C1 N1 H1B 109.2 . . ?
C1 N1 C2 112.0(2) . . ?
C2 N1 H1A 109.2 . . ?
C2 N1 H1B 109.2 . . ?
H1E O1 H1F 104.5 . . ?
C4 N2 H2 118.3 . . ?
C4 N2 C5 123.3(3) . . ?
C5 N2 H2 118.3 . . ?
C7 C3 C2 121.6(2) . . ?
C4 C3 C7 118.1(3) . . ?
C4 C3 C2 120.3(3) . . ?
N1 C1 C1 109.7(3) . 3_576 ?
N1 C1 H1C 109.7 . . ?
N1 C1 H1D 109.7 . . ?
C1 C1 H1C 109.7 3_576 . ?
C1 C1 H1D 109.7 3_576 . ?
H1C C1 H1D 108.2 . . ?
C3 C7 H7 119.8 . . ?
C3 C7 C6 120.3(3) . . ?
C6 C7 H7 119.8 . . ?
N1 C2 C3 111.4(2) . . ?
N1 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
C3 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
N2 C4 C3 119.7(3) . . ?
N2 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C7 C6 H6 120.4 . . ?
C5 C6 C7 119.3(3) . . ?
C5 C6 H6 120.4 . . ?
N2 C5 C6 119.2(3) . . ?
N2 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?

_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_20180403_4a_0m
_database_code_depnum_ccdc_archive 'CCDC 1958979'
loop_
_audit_author_name
_audit_author_address
'Hai-Dong Lv'
;College of Chemistry, Liaoning University
China
;
_audit_update_record             
;
2019-10-12 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;
_audit_creation_date             2018-06-02
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Cl4 Zn), C14 H22 N4'
_chemical_formula_sum            'C14 H22 Cl8 N4 Zn2'
_chemical_formula_weight         660.69
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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                   10.2666(6)
_cell_length_b                   9.5232(6)
_cell_length_c                   13.0868(8)
_cell_angle_alpha                90
_cell_angle_beta                 106.857(2)
_cell_angle_gamma                90
_cell_volume                     1224.53(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9846
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.337
_cell_measurement_theta_min      3.092
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.841
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1002 before and 0.0469 after correction.
The Ratio of minimum to maximum transmission is 0.7268.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_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            20162
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         28.337
_diffrn_reflns_theta_min         3.093
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2808
_reflns_number_total             2993
_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 v8.37A (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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2993
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0268
_refine_ls_restrained_S_all      1.121
_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)+(0.0270P)²+0.9310P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0648
_refine_ls_wR_factor_ref         0.0662
_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, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C1(H1C,H1D), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C7(H7), C4(H4), C6(H6), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Zn1 Zn 0.98704(2) -0.02489(2) 0.74240(2) 0.02750(8) Uani 1 1 d . . . . .
Cl2 Cl 0.86212(5) 0.15594(5) 0.77928(4) 0.03739(12) Uani 1 1 d . . . . .
Cl1 Cl 0.85299(5) -0.12198(5) 0.58886(4) 0.03648(11) Uani 1 1 d . . . . .
Cl3 Cl 1.18220(5) 0.05699(6) 0.72143(4) 0.04105(13) Uani 1 1 d . . . . .
Cl4 Cl 1.03749(6) -0.18703(6) 0.87554(5) 0.04955(15) Uani 1 1 d . . . . .
N1 N 0.64333(15) 0.12956(15) 0.52253(12) 0.0261(3) Uani 1 1 d . . . . .
H1A H 0.7076 0.0747 0.5636 0.031 Uiso 1 1 calc R . . . .
H1B H 0.6142 0.1867 0.5651 0.031 Uiso 1 1 calc R . . . .
C3 C 0.80557(17) 0.31757(18) 0.51756(14) 0.0252(3) Uani 1 1 d . . . . .
N2 N 0.8517(2) 0.53582(18) 0.60417(18) 0.0440(4) Uani 1 1 d . . . . .
H2 H 0.8226 0.6157 0.6190 0.053 Uiso 1 1 calc R . . . .
C1 C 0.52829(19) 0.04082(19) 0.46144(15) 0.0302(4) Uani 1 1 d . . . . .
H1C H 0.5594 -0.0238 0.4162 0.036 Uiso 1 1 calc R . . . .
H1D H 0.4576 0.0995 0.4162 0.036 Uiso 1 1 calc R . . . .
C7 C 0.94259(19) 0.28611(19) 0.55582(16) 0.0312(4) Uani 1 1 d . . . . .
H7 H 0.9746 0.2001 0.5396 0.037 Uiso 1 1 calc R . . . .
C2 C 0.7039(2) 0.2157(2) 0.45187(15) 0.0335(4) Uani 1 1 d . . . . .
H2A H 0.6324 0.2666 0.4004 0.040 Uiso 1 1 calc R . . . .
H2B H 0.7482 0.1545 0.4129 0.040 Uiso 1 1 calc R . . . .
C4 C 0.76233(19) 0.4450(2) 0.54414(18) 0.0359(4) Uani 1 1 d . . . . .
H4 H 0.6705 0.4684 0.5203 0.043 Uiso 1 1 calc R . . . .
C6 C 1.03248(19) 0.3825(2) 0.61837(17) 0.0369(4) Uani 1 1 d . . . . .
H6 H 1.1247 0.3616 0.6438 0.044 Uiso 1 1 calc R . . . .
C5 C 0.9847(2) 0.5073(2) 0.64205(18) 0.0397(4) Uani 1 1 d . . . . .
H5 H 1.0438 0.5726 0.6842 0.048 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
Zn1 Cl2 2.2809(5) . ?
Zn1 Cl1 2.2766(5) . ?
Zn1 Cl3 2.2397(5) . ?
Zn1 Cl4 2.2726(5) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 C1 1.483(2) . ?
N1 C2 1.500(2) . ?
C3 C7 1.382(2) . ?
C3 C2 1.500(2) . ?
C3 C4 1.372(3) . ?
N2 H2 0.8600 . ?
N2 C4 1.337(3) . ?
N2 C5 1.338(3) . ?
C1 C1 1.517(4) 3_656 ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C7 H7 0.9300 . ?
C7 C6 1.388(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C4 H4 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.356(3) . ?
C5 H5 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
Cl1 Zn1 Cl2 105.09(2) . . ?
Cl3 Zn1 Cl2 109.94(2) . . ?
Cl3 Zn1 Cl1 111.50(2) . . ?
Cl3 Zn1 Cl4 108.51(2) . . ?
Cl4 Zn1 Cl2 111.58(2) . . ?
Cl4 Zn1 Cl1 110.23(2) . . ?
H1A N1 H1B 107.8 . . ?
C1 N1 H1A 109.0 . . ?
C1 N1 H1B 109.0 . . ?
C1 N1 C2 112.78(14) . . ?
C2 N1 H1A 109.0 . . ?
C2 N1 H1B 109.0 . . ?
C7 C3 C2 122.24(17) . . ?
C4 C3 C7 118.05(17) . . ?
C4 C3 C2 119.68(17) . . ?
C4 N2 H2 118.7 . . ?
C4 N2 C5 122.61(18) . . ?
C5 N2 H2 118.7 . . ?
N1 C1 C1 109.39(18) . 3_656 ?
N1 C1 H1C 109.8 . . ?
N1 C1 H1D 109.8 . . ?
C1 C1 H1C 109.8 3_656 . ?
C1 C1 H1D 109.8 3_656 . ?
H1C C1 H1D 108.2 . . ?
C3 C7 H7 119.9 . . ?
C3 C7 C6 120.21(17) . . ?
C6 C7 H7 119.9 . . ?
N1 C2 C3 110.16(14) . . ?
N1 C2 H2A 109.6 . . ?
N1 C2 H2B 109.6 . . ?
C3 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C3 C4 H4 119.9 . . ?
N2 C4 C3 120.25(18) . . ?
N2 C4 H4 119.9 . . ?
C7 C6 H6 120.3 . . ?
C5 C6 C7 119.46(18) . . ?
C5 C6 H6 120.3 . . ?
N2 C5 C6 119.42(19) . . ?
N2 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?

_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_20190411_1a_0m
_database_code_depnum_ccdc_archive 'CCDC 1958985'
loop_
_audit_author_name
_audit_author_address
'Hai-Dong Lv'
;College of Chemistry, Liaoning University
China
;
_audit_update_record             
;
2019-10-12 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;
_audit_creation_date             2019-04-25
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(I), C14 H22 N4, 2(C H4 O)'
_chemical_formula_sum            'C16 H30 I4 N4 O2'
_chemical_formula_weight         818.04
_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                   8.0705(6)
_cell_length_b                   20.8072(16)
_cell_length_c                   7.8346(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.907(3)
_cell_angle_gamma                90
_cell_volume                     1312.56(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9148
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.308
_cell_measurement_theta_min      3.260
_shelx_estimated_absorpt_T_max   0.732
_shelx_estimated_absorpt_T_min   0.449
_exptl_absorpt_coefficient_mu    4.764
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.2605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1292 before and 0.0577 after correction.
The Ratio of minimum to maximum transmission is 0.3493.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.070
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             764
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            16112
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.260
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2201
_reflns_number_total             2253
_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 v8.37A (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    ?
_refine_diff_density_max         0.968
_refine_diff_density_min         -0.917
_refine_diff_density_rms         0.124
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.200
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.200
_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)+(0.0140P)²+9.2472P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0947
_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, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C2(H2A,H2B), C1(H1C,H1D)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C7(H7), C4(H4), C6(H6), C5(H5)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
2.d 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 1.09585(5) 0.69397(2) 0.55071(6) 0.04732(18) Uani 1 1 d . . . . .
I2 I 0.61193(7) 0.56229(2) 0.75196(6) 0.05287(19) Uani 1 1 d . . . . .
N1 N 0.8577(7) 0.5636(2) 0.4042(7) 0.0372(12) Uani 1 1 d . . . . .
H1A H 0.9361 0.5937 0.4046 0.045 Uiso 1 1 calc R . . . .
H1B H 0.7990 0.5704 0.4946 0.045 Uiso 1 1 calc R . . . .
C3 C 0.6627(7) 0.6355(3) 0.2476(8) 0.0328(13) Uani 1 1 d . . . . .
N2 N 0.4338(7) 0.6992(3) 0.3073(9) 0.0539(16) Uani 1 1 d . . . . .
H2 H 0.3348 0.7016 0.3408 0.065 Uiso 1 1 calc R . . . .
C2 C 0.7461(9) 0.5710(3) 0.2465(8) 0.0404(15) Uani 1 1 d . . . . .
H2A H 0.6630 0.5373 0.2412 0.048 Uiso 1 1 calc R . . . .
H2B H 0.8100 0.5674 0.1464 0.048 Uiso 1 1 calc R . . . .
C7 C 0.5056(8) 0.6410(3) 0.3030(9) 0.0441(16) Uani 1 1 d . . . . .
H7 H 0.4493 0.6048 0.3374 0.053 Uiso 1 1 calc R . . . .
C4 C 0.7403(8) 0.6908(3) 0.2000(9) 0.0435(16) Uani 1 1 d . . . . .
H4 H 0.8466 0.6885 0.1614 0.052 Uiso 1 1 calc R . . . .
C1 C 0.9384(9) 0.5002(3) 0.4225(9) 0.0419(15) Uani 1 1 d . . . . .
H1C H 0.9956 0.4906 0.3205 0.050 Uiso 1 1 calc R . . . .
H1D H 0.8550 0.4673 0.4352 0.050 Uiso 1 1 calc R . . . .
C6 C 0.5070(10) 0.7530(4) 0.2629(10) 0.0533(18) Uani 1 1 d . . . . .
H6 H 0.4526 0.7922 0.2687 0.064 Uiso 1 1 calc R . . . .
C5 C 0.6625(9) 0.7499(3) 0.2088(10) 0.0507(18) Uani 1 1 d . . . . .
H5 H 0.7166 0.7871 0.1778 0.061 Uiso 1 1 calc R . . . .
C8 C 1.1510(16) 0.6022(6) -0.0022(13) 0.090(3) Uani 1 1 d . . . . .
H8A H 1.0574 0.5907 -0.0783 0.135 Uiso 1 1 calc GR . . . .
H8B H 1.2509 0.5860 -0.0464 0.135 Uiso 1 1 calc GR . . . .
H8C H 1.1577 0.6482 0.0073 0.135 Uiso 1 1 calc GR . . . .
O1 O 1.1329(15) 0.5769(9) 0.1516(19) 0.179(6) Uani 1 1 d . . . . .
H1 H 1.2191 0.5586 0.1855 0.269 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
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 C2 1.487(8) . ?
N1 C1 1.474(8) . ?
C3 C2 1.501(8) . ?
C3 C7 1.372(9) . ?
C3 C4 1.374(9) . ?
N2 H2 0.8600 . ?
N2 C7 1.342(10) . ?
N2 C6 1.324(10) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C7 H7 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.383(10) . ?
C1 C1 1.516(13) 3_766 ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C6 H6 0.9300 . ?
C6 C5 1.353(11) . ?
C5 H5 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C8 O1 1.333(15) . ?
O1 H1 0.8200 . ?

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
H1A N1 H1B 107.6 . . ?
C2 N1 H1A 108.7 . . ?
C2 N1 H1B 108.7 . . ?
C1 N1 H1A 108.7 . . ?
C1 N1 H1B 108.7 . . ?
C1 N1 C2 114.4(5) . . ?
C7 C3 C2 120.1(6) . . ?
C7 C3 C4 117.6(6) . . ?
C4 C3 C2 122.3(6) . . ?
C7 N2 H2 118.2 . . ?
C6 N2 H2 118.2 . . ?
C6 N2 C7 123.7(6) . . ?
N1 C2 C3 109.6(5) . . ?
N1 C2 H2A 109.8 . . ?
N1 C2 H2B 109.8 . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
C3 C7 H7 120.2 . . ?
N2 C7 C3 119.6(6) . . ?
N2 C7 H7 120.2 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.9(6) . . ?
C5 C4 H4 119.6 . . ?
N1 C1 C1 110.1(7) . 3_766 ?
N1 C1 H1C 109.6 . . ?
N1 C1 H1D 109.6 . . ?
C1 C1 H1C 109.6 3_766 . ?
C1 C1 H1D 109.6 3_766 . ?
H1C C1 H1D 108.2 . . ?
N2 C6 H6 120.6 . . ?
N2 C6 C5 118.8(7) . . ?
C5 C6 H6 120.6 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.5(7) . . ?
C6 C5 H5 120.3 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
C8 O1 H1 109.5 . . ?

_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_20180710_4a_0m
_database_code_depnum_ccdc_archive 'CCDC 1958978'
loop_
_audit_author_name
_audit_author_address
'Hai-Dong Lv'
;College of Chemistry, Liaoning University
China
;
_audit_update_record             
;
2019-10-12 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;
_audit_creation_date             2018-07-12
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Br4 Cu), C14 H22 N4'
_chemical_formula_sum            'C14 H22 Br8 Cu2 N4'
_chemical_formula_weight         1012.71
_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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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      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                   7.7157(13)
_cell_length_b                   22.709(4)
_cell_length_c                   7.5681(13)
_cell_angle_alpha                90
_cell_angle_beta                 90.842(7)
_cell_angle_gamma                90
_cell_volume                     1325.9(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.388
_cell_measurement_theta_min      3.192
_shelx_estimated_absorpt_T_max   0.408
_shelx_estimated_absorpt_T_min   0.145
_exptl_absorpt_coefficient_mu    13.668
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.2330
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1757 before and 0.0856 after correction.
The Ratio of minimum to maximum transmission is 0.3125.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    2.537
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20406
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         28.434
_diffrn_reflns_theta_min         3.193
_diffrn_ambient_temperature      273
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2949
_reflns_number_total             3321
_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 v8.37A (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 (Sheldrick, 2015)'
_refine_diff_density_max         2.087
_refine_diff_density_min         -1.784
_refine_diff_density_rms         0.290
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         3321
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0662
_refine_ls_restrained_S_all      1.197
_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)+(0.0606P)²+14.8758P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1533
_refine_ls_wR_factor_ref         0.1578
_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,H) groups
2.a Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C2(H2A,H2B), C1(H1C,H1D)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C6(H6), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_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
Br4 Br 0.20728(10) 0.88650(4) 0.76197(10) 0.0278(2) Uani 1 1 d . . . . .
Br1 Br 0.52846(11) 0.80405(4) 0.99420(12) 0.0318(2) Uani 1 1 d . . . . .
Br2 Br 0.57853(11) 0.91194(5) 0.50189(11) 0.0370(2) Uani 1 1 d . . . . .
Cu1 Cu 0.51498(12) 0.88705(4) 0.79942(13) 0.0265(2) Uani 1 1 d . . . . .
Br3 Br 0.73769(17) 0.94263(5) 0.93812(15) 0.0610(4) Uani 1 1 d . . . . .
N1 N 0.1746(7) 0.5388(3) 0.8756(8) 0.0173(11) Uani 1 1 d . . . . .
H1A H 0.2261 0.5059 0.8400 0.021 Uiso 1 1 calc R . . . .
H1B H 0.2344 0.5527 0.9680 0.021 Uiso 1 1 calc R . . . .
N2 N 0.1636(10) 0.7392(3) 0.8763(10) 0.0327(16) Uani 1 1 d . . . . .
C2 C 0.1800(11) 0.5835(3) 0.7282(9) 0.0232(15) Uani 1 1 d . . . . .
H2A H 0.2989 0.5879 0.6906 0.028 Uiso 1 1 calc R . . . .
H2B H 0.1127 0.5688 0.6284 0.028 Uiso 1 1 calc R . . . .
C3 C 0.1114(9) 0.6424(3) 0.7794(9) 0.0188(13) Uani 1 1 d . . . . .
C1 C -0.0035(9) 0.5246(3) 0.9318(9) 0.0190(13) Uani 1 1 d . . . . .
H1C H -0.0728 0.5122 0.8304 0.023 Uiso 1 1 calc R . . . .
H1D H -0.0571 0.5592 0.9823 0.023 Uiso 1 1 calc R . . . .
C4 C -0.0625(10) 0.6563(3) 0.7662(10) 0.0230(14) Uani 1 1 d . . . . .
H4 H -0.1412 0.6282 0.7255 0.028 Uiso 1 1 calc R . . . .
C7 C 0.2243(10) 0.6860(3) 0.8368(10) 0.0254(15) Uani 1 1 d . . . . .
H7 H 0.3422 0.6781 0.8479 0.030 Uiso 1 1 calc R . . . .
C6 C -0.0036(13) 0.7532(4) 0.8664(11) 0.0318(18) Uani 1 1 d . . . . .
H6 H -0.0400 0.7910 0.8956 0.038 Uiso 1 1 calc R . . . .
C5 C -0.1207(11) 0.7120(4) 0.8133(12) 0.0308(17) Uani 1 1 d . . . . .
H5 H -0.2384 0.7208 0.8086 0.037 Uiso 1 1 calc R . . . .
H2 H 0.221(15) 0.765(5) 0.916(15) 0.04(3) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br4 Cu1 2.3869(13) . ?
Br1 Cu1 2.3940(13) . ?
Br2 Cu1 2.3797(13) . ?
Cu1 Br3 2.3653(14) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 C2 1.509(9) . ?
N1 C1 1.480(9) . ?
N2 C7 1.330(11) . ?
N2 C6 1.329(12) . ?
N2 H2 0.80(12) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.491(10) . ?
C3 C4 1.380(10) . ?
C3 C7 1.385(10) . ?
C1 C1 1.521(14) 3_567 ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C4 H4 0.9300 . ?
C4 C5 1.390(11) . ?
C7 H7 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.358(12) . ?
C5 H5 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
Br4 Cu1 Br1 95.92(4) . . ?
Br2 Cu1 Br4 96.16(4) . . ?
Br2 Cu1 Br1 139.64(6) . . ?
Br3 Cu1 Br4 140.38(7) . . ?
Br3 Cu1 Br1 97.02(5) . . ?
Br3 Cu1 Br2 97.74(5) . . ?
H1A N1 H1B 107.7 . . ?
C2 N1 H1A 108.9 . . ?
C2 N1 H1B 108.9 . . ?
C1 N1 H1A 108.9 . . ?
C1 N1 H1B 108.9 . . ?
C1 N1 C2 113.3(6) . . ?
C7 N2 H2 125(8) . . ?
C6 N2 C7 123.3(7) . . ?
C6 N2 H2 112(8) . . ?
N1 C2 H2A 108.9 . . ?
N1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 N1 113.4(5) . . ?
C3 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C4 C3 C2 122.3(7) . . ?
C4 C3 C7 117.8(7) . . ?
C7 C3 C2 119.9(7) . . ?
N1 C1 C1 109.4(7) . 3_567 ?
N1 C1 H1C 109.8 . . ?
N1 C1 H1D 109.8 . . ?
C1 C1 H1C 109.8 3_567 . ?
C1 C1 H1D 109.8 3_567 . ?
H1C C1 H1D 108.3 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.4(7) . . ?
C5 C4 H4 119.8 . . ?
N2 C7 C3 119.8(7) . . ?
N2 C7 H7 120.1 . . ?
C3 C7 H7 120.1 . . ?
N2 C6 H6 120.3 . . ?
N2 C6 C5 119.5(8) . . ?
C5 C6 H6 120.3 . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.1(8) . . ?
C6 C5 H5 120.4 . . ?

_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_20180411_2a_0m
_database_code_depnum_ccdc_archive 'CCDC 1958983'
loop_
_audit_author_name
_audit_author_address
'Hai-Dong Lv'
;College of Chemistry, Liaoning University
China
;
_audit_update_record             
;
2020-02-23 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;
_audit_creation_date             2020-02-22
_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         'C14 H20 Br6 N4 Zn2, 2(C H4 O)'
_chemical_formula_sum            'C16 H28 Br6 N4 O2 Zn2'
_chemical_formula_weight         918.62
_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'
Br Br -0.2901 2.4595 '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'
Zn Zn 0.2839 1.4301 '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                   7.7044(9)
_cell_length_b                   10.1649(13)
_cell_length_c                   10.5702(13)
_cell_angle_alpha                62.697(4)
_cell_angle_beta                 74.100(5)
_cell_angle_gamma                85.369(5)
_cell_volume                     706.46(15)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    8513
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.355
_cell_measurement_theta_min      3.054
_shelx_estimated_absorpt_T_max   0.535
_shelx_estimated_absorpt_T_min   0.400
_exptl_absorpt_coefficient_mu    10.201
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.1761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1756 before and 0.0907 after correction. The Ratio of minimum to maximum transmission is 0.2362. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.159
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             438
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_Laue_measured_fraction_full 0.862
_diffrn_reflns_Laue_measured_fraction_max 0.860
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5335
_diffrn_reflns_point_group_measured_fraction_full 0.862
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_min         3.055
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.862
_diffrn_measured_fraction_theta_max 0.860
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2119
_reflns_number_total             2268
_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 v8.37A (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 (Sheldrick, 2015)'
_refine_diff_density_max         2.159
_refine_diff_density_min         -1.848
_refine_diff_density_rms         0.341
_refine_ls_extinction_coef       0.064(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.190
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2268
_refine_ls_number_restraints     57
_refine_ls_R_factor_all          0.1191
_refine_ls_R_factor_gt           0.1129
_refine_ls_restrained_S_all      1.175
_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)+(0.0001P)²+58.9608P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2664
_refine_ls_wR_factor_ref         0.2697
_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,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Rigid body (RIGU) restrains
 N1, C1, C3, C7, N2, C6, C5, C4, C2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C1(H1C,H1D), C2(H2A,H2B)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C4(H4), C5(H5)
3.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.6714(3) 0.3965(2) 0.3484(2) 0.0327(7) Uani 1 1 d . . . . .
Br3 Br 0.9560(4) 0.7316(3) -0.0219(3) 0.0434(8) Uani 1 1 d . . . . .
Zn1 Zn 0.7317(3) 0.6608(3) 0.2062(3) 0.0298(8) Uani 1 1 d . . . . .
Br2 Br 0.4554(4) 0.7760(3) 0.1711(3) 0.0526(9) Uani 1 1 d . . . . .
N2 N 0.841(2) 0.7175(18) 0.3308(17) 0.026(3) Uani 1 1 d . U . . .
O1 O 0.606(3) 0.873(2) 0.783(2) 0.057(5) Uani 1 1 d . . . . .
H1 H 0.583701 0.881182 0.859656 0.086 Uiso 1 1 calc GR . . . .
C7 C 0.811(3) 0.631(2) 0.480(2) 0.024(4) Uani 1 1 d . U . . .
H7 H 0.743051 0.541888 0.524449 0.028 Uiso 1 1 calc R . . . .
N1 N 0.648(2) 0.5940(18) 0.8057(16) 0.020(3) Uani 1 1 d . U . . .
H1A H 0.567615 0.584071 0.764086 0.024 Uiso 1 1 calc R . . . .
H1B H 0.647211 0.686561 0.793990 0.024 Uiso 1 1 calc R . . . .
C6 C 0.934(3) 0.847(2) 0.272(2) 0.028(4) Uani 1 1 d . U . . .
H6 H 0.954311 0.908092 0.171239 0.034 Uiso 1 1 calc R . . . .
C1 C 0.595(2) 0.487(2) 0.9699(19) 0.020(4) Uani 1 1 d . U . . .
H1C H 0.605608 0.385145 0.984755 0.025 Uiso 1 1 calc R . . . .
H1D H 0.673659 0.504178 1.019155 0.025 Uiso 1 1 calc R . . . .
C3 C 0.876(2) 0.670(2) 0.567(2) 0.021(3) Uani 1 1 d . U . . .
C2 C 0.834(3) 0.567(2) 0.730(2) 0.027(4) Uani 1 1 d . U . . .
H2A H 0.923229 0.582785 0.770694 0.032 Uiso 1 1 calc R . . . .
H2B H 0.837291 0.464701 0.745426 0.032 Uiso 1 1 calc R . . . .
C4 C 0.971(3) 0.805(2) 0.503(2) 0.032(4) Uani 1 1 d . U . . .
H4 H 1.012633 0.835555 0.560092 0.039 Uiso 1 1 calc R . . . .
C5 C 1.002(3) 0.894(2) 0.351(2) 0.035(4) Uani 1 1 d . U . . .
H5 H 1.067275 0.984821 0.304372 0.042 Uiso 1 1 calc R . . . .
C8 C 0.482(7) 0.948(4) 0.706(5) 0.12(2) Uani 1 1 d . . . . .
H8A H 0.532752 1.044342 0.631385 0.177 Uiso 1 1 calc GR . . . .
H8B H 0.374717 0.957804 0.772643 0.177 Uiso 1 1 calc GR . . . .
H8C H 0.451904 0.893323 0.660299 0.177 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
Br1 Zn1 2.410(3) . ?
Br3 Zn1 2.375(3) . ?
Zn1 Br2 2.382(4) . ?
Zn1 N2 2.039(17) . ?
N2 C7 1.37(2) . ?
N2 C6 1.34(3) . ?
O1 H1 0.8200 . ?
O1 C8 1.37(4) . ?
C7 H7 0.9300 . ?
C7 C3 1.37(3) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 C1 1.52(2) . ?
N1 C2 1.51(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.35(3) . ?
C1 C1 1.49(4) 2_667 ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C3 C2 1.50(3) . ?
C3 C4 1.38(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C4 H4 0.9300 . ?
C4 C5 1.40(3) . ?
C5 H5 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

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
Br3 Zn1 Br1 113.44(13) . . ?
Br3 Zn1 Br2 111.66(14) . . ?
Br2 Zn1 Br1 108.94(13) . . ?
N2 Zn1 Br1 104.3(5) . . ?
N2 Zn1 Br3 105.7(5) . . ?
N2 Zn1 Br2 112.6(5) . . ?
C7 N2 Zn1 121.8(13) . . ?
C6 N2 Zn1 121.3(14) . . ?
C6 N2 C7 116.7(17) . . ?
C8 O1 H1 109.5 . . ?
N2 C7 H7 118.5 . . ?
C3 C7 N2 123.0(17) . . ?
C3 C7 H7 118.5 . . ?
H1A N1 H1B 108.0 . . ?
C1 N1 H1A 109.3 . . ?
C1 N1 H1B 109.3 . . ?
C2 N1 H1A 109.3 . . ?
C2 N1 H1B 109.3 . . ?
C2 N1 C1 111.5(14) . . ?
N2 C6 H6 118.0 . . ?
N2 C6 C5 124.1(19) . . ?
C5 C6 H6 118.0 . . ?
N1 C1 H1C 110.4 . . ?
N1 C1 H1D 110.4 . . ?
C1 C1 N1 106.8(18) 2_667 . ?
C1 C1 H1C 110.4 2_667 . ?
C1 C1 H1D 110.4 2_667 . ?
H1C C1 H1D 108.6 . . ?
C7 C3 C2 118.2(17) . . ?
C7 C3 C4 118.6(18) . . ?
C4 C3 C2 123.1(18) . . ?
N1 C2 H2A 109.7 . . ?
N1 C2 H2B 109.7 . . ?
C3 C2 N1 109.7(15) . . ?
C3 C2 H2A 109.7 . . ?
C3 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.0(19) . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 118.6(19) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 N2 C7 C3 -177.1(15) . . . . ?
Zn1 N2 C6 C5 176.3(17) . . . . ?
N2 C7 C3 C2 179.6(18) . . . . ?
N2 C7 C3 C4 3(3) . . . . ?
N2 C6 C5 C4 -1(3) . . . . ?
C7 N2 C6 C5 1(3) . . . . ?
C7 C3 C2 N1 -83(2) . . . . ?
C7 C3 C4 C5 -2(3) . . . . ?
C6 N2 C7 C3 -2(3) . . . . ?
C1 N1 C2 C3 177.2(15) . . . . ?
C3 C4 C5 C6 2(3) . . . . ?
C2 N1 C1 C1 -174.3(18) . . . 2_667 ?
C2 C3 C4 C5 -179(2) . . . . ?
C4 C3 C2 N1 94(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
