# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1961022'
loop_
_audit_author_name
_audit_author_address
'Xiaoqiang Liang'
;Xian Polytechnic University
China
;
_audit_update_record             
;
2019-10-23 deposited with the CCDC.	2020-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H8 N4'
_chemical_formula_sum            'C9 H8 N4'
_chemical_formula_weight         172.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   6.467(7)
_cell_length_b                   7.524(8)
_cell_length_c                   16.983(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     826.4(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1882
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      24.07


_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.81
_shelx_estimated_absorpt_T_max   0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   SADABS;Bruker,2008
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ' phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5202
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.961
_diffrn_reflns_theta_max         26.583
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1701
_reflns_number_gt                1482
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.669
_reflns_Friedel_fraction_max     0.976
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'SMART (Brucker, 2008)'
_computing_cell_refinement       'SMART '
_computing_data_reduction        'SANIT (Brucker, 2008) '
_computing_structure_solution    'SHELXTL(Brucker, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL(Brucker, 2008)'
_computing_publication_material  'SHELXTL(Brucker, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0678P)²+0.0603P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.053(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 520 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.0(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1701
_refine_ls_number_parameters     119
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1055
_refine_ls_wR_factor_gt          0.1008
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_restrained_S_all      0.955
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7098(4) 0.4907(4) 0.45089(15) 0.0506(7) Uani 1 1 d D . . . .
H1 H 0.8461 0.5278 0.4567 0.061 Uiso 1 1 calc R U . . .
C2 C 0.5531(5) 0.5832(4) 0.48528(16) 0.0523(7) Uani 1 1 d D . . . .
H2 H 0.5869 0.6816 0.5158 0.063 Uiso 1 1 calc R U . . .
C3 C 0.3113(4) 0.3983(4) 0.43465(14) 0.0459(6) Uani 1 1 d . . . . .
H3 H 0.1730 0.3677 0.4284 0.055 Uiso 1 1 calc R U . . .
C4 C 0.4578(3) 0.2926(3) 0.39858(13) 0.0362(5) Uani 1 1 d . . . . .
C5 C 0.6632(4) 0.3412(4) 0.40735(14) 0.0432(6) Uani 1 1 d . . . . .
H5 H 0.7678 0.2743 0.3843 0.052 Uiso 1 1 calc R U . . .
C6 C 0.3939(3) 0.1292(3) 0.35662(12) 0.0340(5) Uani 1 1 d . . . . .
C7 C 0.5138(4) -0.0215(4) 0.35827(14) 0.0422(6) Uani 1 1 d . . . . .
H7 H 0.6421 -0.0238 0.3830 0.051 Uiso 1 1 calc R U . . .
C8 C 0.4335(4) -0.1687(4) 0.32127(13) 0.0421(6) Uani 1 1 d . . . . .
H8 H 0.5109 -0.2729 0.3220 0.051 Uiso 1 1 calc R U . . .
C9 C 0.1485(3) -0.0165(3) 0.28504(13) 0.0371(5) Uani 1 1 d . . . . .
N1 N 0.2117(3) 0.1342(3) 0.31970(11) 0.0373(5) Uani 1 1 d . . . . .
N2 N 0.2536(3) -0.1710(3) 0.28494(11) 0.0414(5) Uani 1 1 d . . . . .
N3 N -0.0319(3) -0.0145(3) 0.24669(15) 0.0549(6) Uani 1 1 d . . . . .
H3A H -0.1038 0.0816 0.2448 0.066 Uiso 1 1 calc R U . . .
H3B H -0.0762 -0.1092 0.2239 0.066 Uiso 1 1 calc R U . . .
N4 N 0.3546(4) 0.5410(3) 0.47776(14) 0.0558(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.361(4) . ?
C1 C5 1.379(4) . ?
C1 H1 0.9300 . ?
C2 N4 1.329(4) . ?
C2 H2 0.9300 . ?
C3 N4 1.329(4) . ?
C3 C4 1.380(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(4) . ?
C4 C6 1.480(3) . ?
C5 H5 0.9300 . ?
C6 N1 1.336(3) . ?
C6 C7 1.374(3) . ?
C7 C8 1.375(4) . ?
C7 H7 0.9300 . ?
C8 N2 1.317(3) . ?
C8 H8 0.9300 . ?
C9 N3 1.337(3) . ?
C9 N1 1.341(3) . ?
C9 N2 1.346(3) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C5 119.0(3) . . ?
C2 C1 H1 120.5 . . ?
C5 C1 H1 120.5 . . ?
N4 C2 C1 123.8(3) . . ?
N4 C2 H2 118.1 . . ?
C1 C2 H2 118.1 . . ?
N4 C3 C4 124.4(3) . . ?
N4 C3 H3 117.8 . . ?
C4 C3 H3 117.8 . . ?
C3 C4 C5 117.2(2) . . ?
C3 C4 C6 120.1(2) . . ?
C5 C4 C6 122.6(2) . . ?
C1 C5 C4 118.8(2) . . ?
C1 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
N1 C6 C7 122.1(2) . . ?
N1 C6 C4 116.7(2) . . ?
C7 C6 C4 121.2(2) . . ?
C6 C7 C8 116.2(2) . . ?
C6 C7 H7 121.9 . . ?
C8 C7 H7 121.9 . . ?
N2 C8 C7 123.9(2) . . ?
N2 C8 H8 118.0 . . ?
C7 C8 H8 118.0 . . ?
N3 C9 N1 118.0(2) . . ?
N3 C9 N2 116.8(2) . . ?
N1 C9 N2 125.2(2) . . ?
C6 N1 C9 116.8(2) . . ?
C8 N2 C9 115.7(2) . . ?
C9 N3 H3A 120.0 . . ?
C9 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C3 N4 C2 116.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C1 C2 N4 -1.9(4) . . . . ?
N4 C3 C4 C5 -1.0(4) . . . . ?
N4 C3 C4 C6 175.6(2) . . . . ?
C2 C1 C5 C4 1.5(4) . . . . ?
C3 C4 C5 C1 -0.1(4) . . . . ?
C6 C4 C5 C1 -176.6(2) . . . . ?
C3 C4 C6 N1 34.3(3) . . . . ?
C5 C4 C6 N1 -149.3(2) . . . . ?
C3 C4 C6 C7 -143.4(2) . . . . ?
C5 C4 C6 C7 33.0(3) . . . . ?
N1 C6 C7 C8 -1.5(3) . . . . ?
C4 C6 C7 C8 176.2(2) . . . . ?
C6 C7 C8 N2 0.6(4) . . . . ?
C7 C6 N1 C9 1.1(3) . . . . ?
C4 C6 N1 C9 -176.7(2) . . . . ?
N3 C9 N1 C6 -179.0(2) . . . . ?
N2 C9 N1 C6 0.3(3) . . . . ?
C7 C8 N2 C9 0.5(3) . . . . ?
N3 C9 N2 C8 178.3(2) . . . . ?
N1 C9 N2 C8 -1.0(3) . . . . ?
C4 C3 N4 C2 0.7(4) . . . . ?
C1 C2 N4 C3 0.9(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3B N1 0.86 2.25 3.100(4) 172.2 3_545
N3 H3A N2 0.86 2.16 3.004(4) 167.5 3
N3 H3A N2 0.86 2.16 3.004(4) 167.5 3
N3 H3B N1 0.86 2.25 3.100(4) 172.2 3_545
N3 H3A N2 0.86 2.16 3.004(4) 167.5 3
N3 H3A N2 0.86 2.16 3.004(4) 167.5 3
N3 H3B N1 0.86 2.25 3.100(4) 172.2 3_545

_refine_diff_density_max         0.151
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.039

_exptl_crystal_preparation       'proton conduction'
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1961024'
loop_
_audit_author_name
_audit_author_address
'Xiaoqiang Liang'
;Xian Polytechnic University
China
;
_audit_update_record             
;
2019-10-23 deposited with the CCDC.	2020-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C60 H54 Co N16 O15'
_chemical_formula_sum            'C60 H54 Co N16 O15'
_chemical_formula_weight         1298.12

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'
Co Co 0.3494 0.9721 '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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.607(6)
_cell_length_b                   10.131(7)
_cell_length_c                   18.949(13)
_cell_angle_alpha                86.816(11)
_cell_angle_beta                 79.942(11)
_cell_angle_gamma                78.363(11)
_cell_volume                     1408.0(18)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4169
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      27.95

_exptl_crystal_description       rod
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_F_000             673
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.393
_shelx_estimated_absorpt_T_min   0.926
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   SADABS;Bruker,2008
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ' phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14439
_diffrn_reflns_av_unetI/netI     0.0680
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.092
_diffrn_reflns_theta_max         28.201
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6810
_reflns_number_gt                5276
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'SMART (Brucker, 2008)'
_computing_cell_refinement       'SMART '
_computing_data_reduction        'SANIT (Brucker, 2008) '
_computing_structure_solution    'SHELXTL(Brucker, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL(Brucker, 2008)'
_computing_publication_material  'SHELXTL(Brucker, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1732P)²+2.2720P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6810
_refine_ls_number_parameters     418
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0850
_refine_ls_wR_factor_ref         0.2776
_refine_ls_wR_factor_gt          0.2511
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0453(5) 0.8547(4) 0.85947(18) 0.0239(7) Uani 1 1 d . . . . .
H1 H 0.0038 0.7900 0.8912 0.029 Uiso 1 1 calc R U . . .
C2 C 0.1059(5) 1.0690(4) 0.83930(19) 0.0239(7) Uani 1 1 d . . . . .
H2 H 0.1041 1.1536 0.8565 0.029 Uiso 1 1 calc R U . . .
C3 C 0.1671(6) 1.0447(4) 0.7671(2) 0.0283(8) Uani 1 1 d . . . . .
H3 H 0.2089 1.1109 0.7365 0.034 Uiso 1 1 calc R U . . .
C4 C 0.1648(6) 0.9206(4) 0.74135(19) 0.0273(8) Uani 1 1 d . . . . .
H4 H 0.2062 0.9020 0.6931 0.033 Uiso 1 1 calc R U . . .
C5 C 0.1000(5) 0.8226(4) 0.78789(18) 0.0205(7) Uani 1 1 d . . . . .
C6 C 0.0883(5) 0.6907(4) 0.75959(18) 0.0216(7) Uani 1 1 d . . . . .
C7 C 0.0207(6) 0.5893(4) 0.80274(19) 0.0293(8) Uani 1 1 d . . . . .
H7 H -0.0132 0.5973 0.8521 0.035 Uiso 1 1 calc R U . . .
C8 C 0.0073(6) 0.4763(4) 0.7675(2) 0.0289(8) Uani 1 1 d . . . . .
H8 H -0.0387 0.4077 0.7946 0.035 Uiso 1 1 calc R U . . .
C9 C 0.1277(6) 0.5622(4) 0.66008(19) 0.0252(8) Uani 1 1 d . . . . .
C10 C -0.1678(5) 1.2956(4) 0.9771(2) 0.0251(7) Uani 1 1 d . . . . .
C11 C -0.3405(5) 1.4025(3) 0.98769(19) 0.0229(7) Uani 1 1 d . . . . .
C12 C -0.3311(5) 1.5367(3) 0.9976(2) 0.0255(7) Uani 1 1 d . . . . .
H12 H -0.2186 1.5608 0.9956 0.031 Uiso 1 1 calc R U . . .
C13 C -0.5096(5) 1.3657(3) 0.9896(2) 0.0252(7) Uani 1 1 d . . . . .
H13A H -0.5154 1.2767 0.9824 0.030 Uiso 1 1 calc R U . . .
C14 C 0.4015(6) -0.0752(4) 0.1561(2) 0.0329(9) Uani 1 1 d . . . . .
H14 H 0.3959 -0.1579 0.1384 0.039 Uiso 1 1 calc R U . . .
C15 C 0.3203(6) -0.0453(4) 0.2258(2) 0.0342(9) Uani 1 1 d . . . . .
H15 H 0.2642 -0.1073 0.2547 0.041 Uiso 1 1 calc R U . . .
C16 C 0.3239(6) 0.0782(4) 0.2518(2) 0.0304(8) Uani 1 1 d . . . . .
H16 H 0.2701 0.1003 0.2987 0.036 Uiso 1 1 calc R U . . .
C17 C 0.4895(6) 0.1283(4) 0.1380(2) 0.0292(8) Uani 1 1 d . . . . .
H17 H 0.5478 0.1876 0.1078 0.035 Uiso 1 1 calc R U . . .
C18 C 0.4085(5) 0.1699(4) 0.20782(18) 0.0223(7) Uani 1 1 d . . . . .
C19 C 0.4183(5) 0.3025(4) 0.23641(19) 0.0229(7) Uani 1 1 d . . . . .
C20 C 0.4841(6) 0.4049(4) 0.1937(2) 0.0310(8) Uani 1 1 d . . . . .
H20 H 0.5184 0.3969 0.1443 0.037 Uiso 1 1 calc R U . . .
C21 C 0.4959(6) 0.5183(4) 0.2282(2) 0.0307(8) Uani 1 1 d . . . . .
H21 H 0.5420 0.5866 0.2009 0.037 Uiso 1 1 calc R U . . .
C22 C 0.3756(6) 0.4327(4) 0.3358(2) 0.0268(8) Uani 1 1 d . . . . .
C23 C 0.5508(5) 0.2361(4) 0.56684(19) 0.0249(7) Uani 1 1 d . . . . .
C24 C 0.5225(5) 0.1134(3) 0.53328(19) 0.0222(7) Uani 1 1 d . . . . .
C25 C 0.5494(5) 0.1088(4) 0.4588(2) 0.0260(8) Uani 1 1 d . . . . .
H25 H 0.5823 0.1815 0.4312 0.031 Uiso 1 1 calc R U . . .
C26 C 0.4727(5) 0.0040(4) 0.57446(19) 0.0258(8) Uani 1 1 d . . . . .
H26 H 0.4543 0.0068 0.6242 0.031 Uiso 1 1 calc R U . . .
C27 C 0.0502(5) 0.2375(4) 0.56510(18) 0.0235(7) Uani 1 1 d . . . . .
C28 C 0.0219(5) 0.1145(3) 0.53195(18) 0.0204(7) Uani 1 1 d . . . . .
C29 C 0.0544(5) 0.1061(4) 0.45796(19) 0.0248(7) Uani 1 1 d . . . . .
H29 H 0.0908 0.1771 0.4298 0.030 Uiso 1 1 calc R U . . .
C30 C -0.0328(5) 0.0078(4) 0.57417(18) 0.0244(7) Uani 1 1 d . . . . .
H30 H -0.0548 0.0132 0.6239 0.029 Uiso 1 1 calc R U . . .
Co1 Co 0.0000 1.0000 1.0000 0.0188(2) Uani 1 2 d S . P . .
N1 N 0.0491(4) 0.9744(3) 0.88539(15) 0.0233(6) Uani 1 1 d . . . . .
N2 N 0.1413(5) 0.6777(3) 0.68965(16) 0.0260(7) Uani 1 1 d . . . . .
N3 N 0.0570(5) 0.4609(3) 0.69695(16) 0.0270(7) Uani 1 1 d . . . . .
N4 N 0.1865(6) 0.5492(4) 0.59032(18) 0.0442(11) Uani 1 1 d . . . . .
H4A H 0.1799 0.4778 0.5692 0.053 Uiso 1 1 d R U . . .
H4B H 0.2313 0.6125 0.5661 0.053 Uiso 1 1 d R U . . .
N5 N 0.4872(5) 0.0079(4) 0.11272(18) 0.0322(8) Uani 1 1 d . . . . .
N6 N 0.3639(5) 0.3161(3) 0.30641(16) 0.0263(7) Uani 1 1 d . . . . .
N7 N 0.3180(6) 0.4460(4) 0.40572(19) 0.0441(10) Uani 1 1 d . . . . .
H7A H 0.2760 0.3822 0.4306 0.053 Uiso 1 1 d R U . . .
H7B H 0.3229 0.5185 0.4262 0.053 Uiso 1 1 d R U . . .
N8 N 0.4444(5) 0.5352(3) 0.29888(17) 0.0291(7) Uani 1 1 d . . . . .
O1 O -0.1894(4) 1.1756(3) 0.99076(15) 0.0303(6) Uani 1 1 d . . . . .
O2 O -0.0188(4) 1.3340(3) 0.9582(2) 0.0509(10) Uani 1 1 d . . . . .
O3 O 0.2131(4) 1.1110(3) 0.99248(15) 0.0298(6) Uani 1 1 d . . . . .
H3A H 0.1876 1.2044 0.9872 0.036 Uiso 1 1 calc R U . . .
H3B H 0.3315 1.0660 0.9945 0.036 Uiso 1 1 calc R U . . .
O4 O 0.6181(5) 0.3217(3) 0.53177(16) 0.0407(8) Uani 1 1 d . . . . .
O5 O 0.5002(5) 0.2412(3) 0.63701(15) 0.0366(7) Uani 1 1 d . . . . .
H5A H 0.5124 0.3134 0.6511 0.044 Uiso 1 1 d R U . . .
O6 O -0.0011(5) 0.2446(3) 0.63476(14) 0.0347(7) Uani 1 1 d . . . . .
H6 H 0.0186 0.3145 0.6487 0.052 Uiso 1 1 calc R U . . .
O7 O 0.1183(5) 0.3223(3) 0.52883(15) 0.0418(8) Uani 1 1 d . . . . .
O8 O 0.5000 1.0000 1.0000 0.0552(14) Uani 1 2 d S . P . .
H8A H 0.4499 0.9252 0.9893 0.083 Uiso 0.5 1 d R U P . .
H8B H 0.6245 0.9890 0.9766 0.083 Uiso 0.5 1 d R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.340(4) . ?
C1 C5 1.384(5) . ?
C1 H1 0.9300 . ?
C2 N1 1.346(5) . ?
C2 C3 1.385(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.398(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.492(5) . ?
C6 N2 1.322(5) . ?
C6 C7 1.401(5) . ?
C7 C8 1.386(5) . ?
C7 H7 0.9300 . ?
C8 N3 1.334(5) . ?
C8 H8 0.9300 . ?
C9 N4 1.324(5) . ?
C9 N2 1.354(4) . ?
C9 N3 1.358(5) . ?
C10 O2 1.259(5) . ?
C10 O1 1.266(5) . ?
C10 C11 1.516(5) . ?
C11 C12 1.400(5) . ?
C11 C13 1.404(5) . ?
C12 C13 1.395(5) 2_487 ?
C12 H12 0.9300 . ?
C13 C12 1.395(5) 2_487 ?
C13 H13A 0.9300 . ?
C14 N5 1.329(6) . ?
C14 C15 1.379(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(6) . ?
C15 H15 0.9300 . ?
C16 C18 1.393(5) . ?
C16 H16 0.9300 . ?
C17 N5 1.339(5) . ?
C17 C18 1.407(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.496(5) . ?
C19 N6 1.325(5) . ?
C19 C20 1.399(5) . ?
C20 C21 1.378(6) . ?
C20 H20 0.9300 . ?
C21 N8 1.339(5) . ?
C21 H21 0.9300 . ?
C22 N7 1.327(5) . ?
C22 N6 1.359(5) . ?
C22 N8 1.360(5) . ?
C23 O4 1.205(5) . ?
C23 O5 1.319(5) . ?
C23 C24 1.497(5) . ?
C24 C25 1.393(5) . ?
C24 C26 1.396(5) . ?
C25 C26 1.388(5) 2_656 ?
C25 H25 0.9300 . ?
C26 C25 1.388(5) 2_656 ?
C26 H26 0.9300 . ?
C27 O7 1.212(5) . ?
C27 O6 1.311(4) . ?
C27 C28 1.495(5) . ?
C28 C29 1.385(5) . ?
C28 C30 1.397(5) . ?
C29 C30 1.385(5) 2_556 ?
C29 H29 0.9300 . ?
C30 C29 1.385(5) 2_556 ?
C30 H30 0.9300 . ?
Co1 O1 2.071(3) . ?
Co1 O1 2.071(3) 2_577 ?
Co1 O3 2.133(3) 2_577 ?
Co1 O3 2.133(3) . ?
Co1 N1 2.159(3) 2_577 ?
Co1 N1 2.159(3) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8601 . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8599 . ?
O3 H3A 0.9300 . ?
O3 H3B 0.9300 . ?
O5 H5A 0.8200 . ?
O6 H6 0.8200 . ?
O8 H8A 0.9600 . ?
O8 H8B 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
N1 C1 C5 123.3(3) . . ?
N1 C1 H1 118.3 . . ?
C5 C1 H1 118.3 . . ?
N1 C2 C3 122.2(3) . . ?
N1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C4 C3 C2 118.8(3) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C1 C5 C4 117.4(3) . . ?
C1 C5 C6 122.5(3) . . ?
C4 C5 C6 120.0(3) . . ?
N2 C6 C7 121.9(3) . . ?
N2 C6 C5 114.9(3) . . ?
C7 C6 C5 123.2(3) . . ?
C8 C7 C6 116.1(3) . . ?
C8 C7 H7 121.9 . . ?
C6 C7 H7 121.9 . . ?
N3 C8 C7 123.5(3) . . ?
N3 C8 H8 118.3 . . ?
C7 C8 H8 118.3 . . ?
N4 C9 N2 117.1(3) . . ?
N4 C9 N3 118.5(3) . . ?
N2 C9 N3 124.4(3) . . ?
O2 C10 O1 126.6(3) . . ?
O2 C10 C11 117.8(3) . . ?
O1 C10 C11 115.5(3) . . ?
C12 C11 C13 120.4(3) . . ?
C12 C11 C10 119.9(3) . . ?
C13 C11 C10 119.7(3) . . ?
C13 C12 C11 120.0(4) 2_487 . ?
C13 C12 H12 120.0 2_487 . ?
C11 C12 H12 120.0 . . ?
C12 C13 C11 119.6(3) 2_487 . ?
C12 C13 H13A 120.2 2_487 . ?
C11 C13 H13A 120.2 . . ?
N5 C14 C15 123.4(4) . . ?
N5 C14 H14 118.3 . . ?
C15 C14 H14 118.3 . . ?
C14 C15 C16 118.8(4) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C15 C16 C18 119.9(3) . . ?
C15 C16 H16 120.1 . . ?
C18 C16 H16 120.1 . . ?
N5 C17 C18 123.5(4) . . ?
N5 C17 H17 118.3 . . ?
C18 C17 H17 118.3 . . ?
C16 C18 C17 116.7(3) . . ?
C16 C18 C19 120.2(3) . . ?
C17 C18 C19 123.0(3) . . ?
N6 C19 C20 121.4(3) . . ?
N6 C19 C18 115.2(3) . . ?
C20 C19 C18 123.4(3) . . ?
C21 C20 C19 116.9(3) . . ?
C21 C20 H20 121.6 . . ?
C19 C20 H20 121.6 . . ?
N8 C21 C20 123.5(4) . . ?
N8 C21 H21 118.3 . . ?
C20 C21 H21 118.3 . . ?
N7 C22 N6 117.2(3) . . ?
N7 C22 N8 118.0(3) . . ?
N6 C22 N8 124.8(3) . . ?
O4 C23 O5 123.3(3) . . ?
O4 C23 C24 121.7(3) . . ?
O5 C23 C24 115.0(3) . . ?
C25 C24 C26 119.7(3) . . ?
C25 C24 C23 118.4(3) . . ?
C26 C24 C23 121.9(3) . . ?
C26 C25 C24 120.2(3) 2_656 . ?
C26 C25 H25 119.9 2_656 . ?
C24 C25 H25 119.9 . . ?
C25 C26 C24 120.1(3) 2_656 . ?
C25 C26 H26 119.9 2_656 . ?
C24 C26 H26 119.9 . . ?
O7 C27 O6 123.7(3) . . ?
O7 C27 C28 120.9(3) . . ?
O6 C27 C28 115.4(3) . . ?
C29 C28 C30 119.8(3) . . ?
C29 C28 C27 118.9(3) . . ?
C30 C28 C27 121.3(3) . . ?
C30 C29 C28 120.2(3) 2_556 . ?
C30 C29 H29 119.9 2_556 . ?
C28 C29 H29 119.9 . . ?
C29 C30 C28 120.0(3) 2_556 . ?
C29 C30 H30 120.0 2_556 . ?
C28 C30 H30 120.0 . . ?
O1 Co1 O1 180.0 . 2_577 ?
O1 Co1 O3 88.79(13) . 2_577 ?
O1 Co1 O3 91.21(12) 2_577 2_577 ?
O1 Co1 O3 91.21(12) . . ?
O1 Co1 O3 88.79(12) 2_577 . ?
O3 Co1 O3 180.0 2_577 . ?
O1 Co1 N1 88.89(12) . 2_577 ?
O1 Co1 N1 91.12(12) 2_577 2_577 ?
O3 Co1 N1 91.68(11) 2_577 2_577 ?
O3 Co1 N1 88.32(11) . 2_577 ?
O1 Co1 N1 91.11(12) . . ?
O1 Co1 N1 88.88(12) 2_577 . ?
O3 Co1 N1 88.32(11) 2_577 . ?
O3 Co1 N1 91.68(11) . . ?
N1 Co1 N1 180.00(16) 2_577 . ?
C1 N1 C2 118.4(3) . . ?
C1 N1 Co1 119.2(2) . . ?
C2 N1 Co1 121.9(2) . . ?
C6 N2 C9 117.9(3) . . ?
C8 N3 C9 116.1(3) . . ?
C9 N4 H4A 120.3 . . ?
C9 N4 H4B 119.7 . . ?
H4A N4 H4B 120.0 . . ?
C14 N5 C17 117.7(3) . . ?
C19 N6 C22 117.8(3) . . ?
C22 N7 H7A 120.1 . . ?
C22 N7 H7B 119.9 . . ?
H7A N7 H7B 120.0 . . ?
C21 N8 C22 115.6(3) . . ?
C10 O1 Co1 130.4(3) . . ?
Co1 O3 H3A 120.0 . . ?
Co1 O3 H3B 120.0 . . ?
H3A O3 H3B 120.0 . . ?
C23 O5 H5A 109.5 . . ?
C27 O6 H6 109.5 . . ?
H8A O8 H8B 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
N1 C2 C3 C4 1.8(6) . . . . ?
C2 C3 C4 C5 0.5(6) . . . . ?
N1 C1 C5 C4 1.0(6) . . . . ?
N1 C1 C5 C6 -177.7(3) . . . . ?
C3 C4 C5 C1 -1.9(6) . . . . ?
C3 C4 C5 C6 176.9(4) . . . . ?
C1 C5 C6 N2 178.1(4) . . . . ?
C4 C5 C6 N2 -0.5(5) . . . . ?
C1 C5 C6 C7 0.3(6) . . . . ?
C4 C5 C6 C7 -178.4(4) . . . . ?
N2 C6 C7 C8 -1.9(6) . . . . ?
C5 C6 C7 C8 175.8(4) . . . . ?
C6 C7 C8 N3 0.9(6) . . . . ?
O2 C10 C11 C12 -18.9(5) . . . . ?
O1 C10 C11 C12 158.9(3) . . . . ?
O2 C10 C11 C13 162.9(4) . . . . ?
O1 C10 C11 C13 -19.3(5) . . . . ?
C13 C11 C12 C13 0.9(6) . . . 2_487 ?
C10 C11 C12 C13 -177.2(3) . . . 2_487 ?
C12 C11 C13 C12 -0.9(6) . . . 2_487 ?
C10 C11 C13 C12 177.2(3) . . . 2_487 ?
N5 C14 C15 C16 1.6(7) . . . . ?
C14 C15 C16 C18 0.0(7) . . . . ?
C15 C16 C18 C17 -1.0(6) . . . . ?
C15 C16 C18 C19 -178.0(4) . . . . ?
N5 C17 C18 C16 0.6(6) . . . . ?
N5 C17 C18 C19 177.5(4) . . . . ?
C16 C18 C19 N6 8.4(5) . . . . ?
C17 C18 C19 N6 -168.4(4) . . . . ?
C16 C18 C19 C20 -173.3(4) . . . . ?
C17 C18 C19 C20 9.9(6) . . . . ?
N6 C19 C20 C21 2.3(6) . . . . ?
C18 C19 C20 C21 -176.0(4) . . . . ?
C19 C20 C21 N8 -1.5(7) . . . . ?
O4 C23 C24 C25 -9.8(6) . . . . ?
O5 C23 C24 C25 171.5(4) . . . . ?
O4 C23 C24 C26 169.4(4) . . . . ?
O5 C23 C24 C26 -9.3(6) . . . . ?
C26 C24 C25 C26 -0.1(6) . . . 2_656 ?
C23 C24 C25 C26 179.0(4) . . . 2_656 ?
C25 C24 C26 C25 0.1(6) . . . 2_656 ?
C23 C24 C26 C25 -179.0(4) . . . 2_656 ?
O7 C27 C28 C29 -7.7(6) . . . . ?
O6 C27 C28 C29 173.2(4) . . . . ?
O7 C27 C28 C30 171.1(4) . . . . ?
O6 C27 C28 C30 -8.1(5) . . . . ?
C30 C28 C29 C30 -0.1(6) . . . 2_556 ?
C27 C28 C29 C30 178.7(3) . . . 2_556 ?
C29 C28 C30 C29 0.1(6) . . . 2_556 ?
C27 C28 C30 C29 -178.7(4) . . . 2_556 ?
C5 C1 N1 C2 1.2(6) . . . . ?
C5 C1 N1 Co1 -170.5(3) . . . . ?
C3 C2 N1 C1 -2.7(6) . . . . ?
C3 C2 N1 Co1 168.8(3) . . . . ?
C7 C6 N2 C9 0.3(6) . . . . ?
C5 C6 N2 C9 -177.6(3) . . . . ?
N4 C9 N2 C6 -178.0(4) . . . . ?
N3 C9 N2 C6 2.5(6) . . . . ?
C7 C8 N3 C9 1.6(6) . . . . ?
N4 C9 N3 C8 177.1(4) . . . . ?
N2 C9 N3 C8 -3.4(6) . . . . ?
C15 C14 N5 C17 -2.0(6) . . . . ?
C18 C17 N5 C14 0.9(6) . . . . ?
C20 C19 N6 C22 -0.6(6) . . . . ?
C18 C19 N6 C22 177.8(3) . . . . ?
N7 C22 N6 C19 178.9(4) . . . . ?
N8 C22 N6 C19 -2.1(6) . . . . ?
C20 C21 N8 C22 -0.9(6) . . . . ?
N7 C22 N8 C21 -178.2(4) . . . . ?
N6 C22 N8 C21 2.8(6) . . . . ?
O2 C10 O1 Co1 8.1(6) . . . . ?
C11 C10 O1 Co1 -169.4(2) . . . . ?

_refine_diff_density_max         1.600
_refine_diff_density_min         -1.211
_refine_diff_density_rms         0.190


_exptl_crystal_preparation       'proton conduction'
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1961023'
loop_
_audit_author_name
_audit_author_address
'Xiaoqiang Liang'
;Xian Polytechnic University
China
;
_audit_update_record             
;
2019-10-23 deposited with the CCDC.	2020-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H8 Cu I N4'
_chemical_formula_sum            'C9 H8 Cu I N4'
_chemical_formula_weight         362.63

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'
Cu Cu 0.3201 1.2651 '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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.337(12)
_cell_length_b                   8.408(14)
_cell_length_c                   9.584(16)
_cell_angle_alpha                106.70(2)
_cell_angle_beta                 98.23(3)
_cell_angle_gamma                107.36(2)
_cell_volume                     523.3(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1439
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      28.16

_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.301
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    5.006
_shelx_estimated_absorpt_T_min   0.368
_shelx_estimated_absorpt_T_max   0.690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.40
_exptl_absorpt_correction_T_max  0.68
_exptl_absorpt_process_details   SADABS;Bruker,2008
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ' phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2895
_diffrn_reflns_av_unetI/netI     0.0807
_diffrn_reflns_av_R_equivalents  0.1104
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.709
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.026
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             1826
_reflns_number_gt                1636
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'SMART (Brucker, 2008)'
_computing_cell_refinement       'SMART '
_computing_data_reduction        'SANIT (Brucker, 2008) '
_computing_structure_solution    'SHELXTL(Brucker, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL(Brucker, 2008)'
_computing_publication_material  'SHELXTL(Brucker, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1055P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1826
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1588
_refine_ls_wR_factor_gt          0.1520
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2979(12) 0.5472(11) 0.1475(9) 0.0276(17) Uani 1 1 d . . . . .
C2 C 0.2167(12) 0.7270(11) 0.0278(8) 0.0263(17) Uani 1 1 d . . . . .
C3 C 0.1310(13) 0.7930(12) 0.1412(9) 0.0322(19) Uani 1 1 d . . . . .
H3 H 0.0704 0.8750 0.1381 0.039 Uiso 1 1 calc R U . . .
C4 C 0.1419(13) 0.7286(13) 0.2595(9) 0.035(2) Uani 1 1 d . . . . .
H4 H 0.0868 0.7700 0.3375 0.042 Uiso 1 1 calc R U . . .
C5 C 0.2969(14) 0.9121(13) 0.6714(9) 0.038(2) Uani 1 1 d . . . . .
H5 H 0.3253 0.9540 0.5942 0.045 Uiso 1 1 calc R U . . .
C6 C 0.2791(13) 1.0294(12) 0.7999(10) 0.0341(19) Uani 1 1 d . . . . .
H6 H 0.2893 1.1444 0.8065 0.041 Uiso 1 1 calc R U . . .
C7 C 0.2460(13) 0.9704(12) 0.9170(9) 0.0324(19) Uani 1 1 d . . . . .
H7 H 0.2336 1.0451 1.0049 0.039 Uiso 1 1 calc R U . . .
C8 C 0.2313(12) 0.7964(11) 0.9019(9) 0.0248(16) Uani 1 1 d . . . . .
C9 C 0.2406(13) 0.6880(11) 0.7659(8) 0.0290(18) Uani 1 1 d . . . . .
H9 H 0.2211 0.5696 0.7529 0.035 Uiso 1 1 calc R U . . .
Cu1 Cu 0.3255(2) 0.58554(17) 0.46900(12) 0.0440(4) Uani 1 1 d . . . . .
I1 I 0.73782(8) 0.73758(7) 0.52725(6) 0.0348(3) Uani 1 1 d . . . . .
N1 N 0.2285(11) 0.6089(10) 0.2669(7) 0.0303(16) Uani 1 1 d . . . . .
N2 N 0.3748(12) 0.4182(10) 0.1435(8) 0.0381(18) Uani 1 1 d . . . . .
H2A H 0.3786 0.3774 0.2162 0.046 Uiso 1 1 calc R U . . .
H2B H 0.4197 0.3772 0.0684 0.046 Uiso 1 1 calc R U . . .
N3 N 0.2995(10) 0.6067(9) 0.0286(7) 0.0271(15) Uani 1 1 d . . . . .
N4 N 0.2763(11) 0.7448(10) 0.6517(7) 0.0315(16) 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
C1 N1 1.349(10) . ?
C1 N2 1.359(11) . ?
C1 N3 1.370(10) . ?
C2 N3 1.328(10) . ?
C2 C3 1.394(11) . ?
C2 C8 1.487(11) 1_554 ?
C3 C4 1.392(12) . ?
C3 H3 0.9300 . ?
C4 N1 1.353(12) . ?
C4 H4 0.9300 . ?
C5 N4 1.323(13) . ?
C5 C6 1.390(13) . ?
C5 H5 0.9300 . ?
C6 C7 1.375(13) . ?
C6 H6 0.9300 . ?
C7 C8 1.397(12) . ?
C7 H7 0.9300 . ?
C8 C9 1.384(11) . ?
C8 C2 1.487(11) 1_556 ?
C9 N4 1.343(11) . ?
C9 H9 0.9300 . ?
Cu1 N4 2.028(7) . ?
Cu1 N1 2.050(7) . ?
Cu1 I1 2.628(5) 2_666 ?
Cu1 I1 2.810(5) . ?
I1 Cu1 2.628(5) 2_666 ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 118.6(7) . . ?
N1 C1 N3 124.9(8) . . ?
N2 C1 N3 116.5(7) . . ?
N3 C2 C3 122.8(7) . . ?
N3 C2 C8 115.7(7) . 1_554 ?
C3 C2 C8 121.3(7) . 1_554 ?
C2 C3 C4 115.8(8) . . ?
C2 C3 H3 122.1 . . ?
C4 C3 H3 122.1 . . ?
N1 C4 C3 123.4(7) . . ?
N1 C4 H4 118.3 . . ?
C3 C4 H4 118.3 . . ?
N4 C5 C6 124.3(8) . . ?
N4 C5 H5 117.8 . . ?
C6 C5 H5 117.8 . . ?
C7 C6 C5 118.0(8) . . ?
C7 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
C6 C7 C8 119.0(8) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C9 C8 C7 118.1(7) . . ?
C9 C8 C2 119.0(8) . 1_556 ?
C7 C8 C2 122.8(7) . 1_556 ?
N4 C9 C8 123.4(8) . . ?
N4 C9 H9 118.3 . . ?
C8 C9 H9 118.3 . . ?
N4 Cu1 N1 116.3(3) . . ?
N4 Cu1 I1 112.5(2) . 2_666 ?
N1 Cu1 I1 117.2(2) . 2_666 ?
N4 Cu1 I1 100.7(2) . . ?
N1 Cu1 I1 103.2(2) . . ?
I1 Cu1 I1 103.99(6) 2_666 . ?
Cu1 I1 Cu1 76.01(6) 2_666 . ?
C1 N1 C4 115.8(7) . . ?
C1 N1 Cu1 120.7(6) . . ?
C4 N1 Cu1 120.8(5) . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C2 N3 C1 117.1(6) . . ?
C5 N4 C9 117.0(7) . . ?
C5 N4 Cu1 122.5(6) . . ?
C9 N4 Cu1 120.1(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
N3 C2 C3 C4 1.7(13) . . . . ?
C8 C2 C3 C4 -174.5(8) 1_554 . . . ?
C2 C3 C4 N1 -0.2(14) . . . . ?
N4 C5 C6 C7 2.9(14) . . . . ?
C5 C6 C7 C8 -0.2(13) . . . . ?
C6 C7 C8 C9 -3.3(12) . . . . ?
C6 C7 C8 C2 173.4(8) . . . 1_556 ?
C7 C8 C9 N4 4.7(13) . . . . ?
C2 C8 C9 N4 -172.2(8) 1_556 . . . ?
N2 C1 N1 C4 -175.7(8) . . . . ?
N3 C1 N1 C4 5.2(13) . . . . ?
N2 C1 N1 Cu1 22.9(11) . . . . ?
N3 C1 N1 Cu1 -156.1(7) . . . . ?
C3 C4 N1 C1 -3.0(14) . . . . ?
C3 C4 N1 Cu1 158.3(7) . . . . ?
C3 C2 N3 C1 0.2(13) . . . . ?
C8 C2 N3 C1 176.6(7) 1_554 . . . ?
N1 C1 N3 C2 -3.9(13) . . . . ?
N2 C1 N3 C2 177.0(8) . . . . ?
C6 C5 N4 C9 -1.7(14) . . . . ?
C6 C5 N4 Cu1 -175.0(7) . . . . ?
C8 C9 N4 C5 -2.2(13) . . . . ?
C8 C9 N4 Cu1 171.3(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2B N3 0.86 2.36 3.115(10) 146.4 2_665
N2 H2A I1 0.86 3.03 3.851(9) 160.1 2_666
C9 H9 I1 0.93 3.27 3.925(9) 129.4 2_666
C5 H5 I1 0.93 3.25 3.987(10) 137.2 2_676
N2 H2B N3 0.86 2.36 3.115(10) 146.4 2_665
C9 H9 I1 0.93 3.27 3.925(9) 129.4 2_666
C5 H5 I1 0.93 3.25 3.987(10) 137.2 2_676
C5 H5 I1 0.93 3.25 3.987(10) 137.2 2_676
C9 H9 I1 0.93 3.27 3.925(9) 129.4 2_666
N2 H2B N3 0.86 2.36 3.115(10) 146.4 2_665

_refine_diff_density_max         2.275
_refine_diff_density_min         -1.336
_refine_diff_density_rms         0.246

_exptl_crystal_preparation       'proton conduction'
