# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_P21onc_a
_database_code_depnum_ccdc_archive 'CCDC 1964373'
loop_
_audit_author_name
_audit_author_address
'Robert Pike'
;College of William and Mary
United States of America
;
_audit_update_record             
;
2019-11-07 deposited with the CCDC.	2019-12-27 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_P21onc_a            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.940 Why?
RESPONSE: This low measured diffraction is the result of limited coverage when using Cu radiation on a three-circle diffractometer in a relatively low-symmetry crystal.
;
_vrf_PLAT315_P21onc_a            
;
PROBLEM: Singly Bonded Carbon Detected (H-atoms Missing).        C1A Check
RESPONSE: This dangling carbon is an artifact of a symmetrically disordered bridging cyano group. The carbon/nitrogen is actually bonded to a crystallographically equivalent carbon/nitrogen across an inversion centre.
;
# Added during the CSD deposition process: Thursday 07 November 2019 03:36 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'N-Butylpyridinium catena-mu2-cyanotri-mu2-iododicopper(I)'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C9 H14 N), C Cu2 I3 N'
_chemical_formula_sum            'C19 H28 Cu2 I3 N3'
_chemical_formula_weight         806.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.8955(4)
_cell_length_b                   8.8088(3)
_cell_length_c                   20.4146(6)
_cell_angle_alpha                90
_cell_angle_beta                 109.9220(10)
_cell_angle_gamma                90
_cell_volume                     2518.33(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9905
_cell_measurement_theta_min      3.16
_cell_measurement_theta_max      69.92

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.126
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.253
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.089
_exptl_absorpt_coefficient_mu    31.018
_shelx_estimated_absorpt_T_min   0.047
_shelx_estimated_absorpt_T_max   0.169
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.0560
_exptl_absorpt_correction_T_max  0.2718
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_special_details           
; 
 ? 
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         Imus
_diffrn_radiation_monochromator  'multi-layer optics'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω and ψ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26524
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.156
_diffrn_reflns_theta_max         66.942
_diffrn_reflns_theta_full        66.942
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measured_fraction_theta_full 0.940
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_Laue_measured_fraction_full 0.940
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_point_group_measured_fraction_full 0.940
_reflns_number_total             4227
_reflns_number_gt                3863
_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINTPLUS (Bruker AXS, 2004)'
_computing_data_reduction        SAINTPLUS
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/5 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXLE (Hubschle, 2011)'
_computing_publication_material  'Mercury 3.7 (CCDC, 2016)'
_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)+(0.0106P)²+18.9816P] 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         4227
_refine_ls_number_parameters     334
_refine_ls_number_restraints     280
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0827
_refine_ls_wR_factor_gt          0.0815
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_restrained_S_all      1.163
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.28093(3) -0.23799(5) 0.57278(2) 0.02691(11) Uani 1 1 d . . . . .
I2 I 0.19365(3) 0.00737(4) 0.38306(2) 0.02615(11) Uani 1 1 d . . . . .
I3 I 0.28363(3) 0.23391(5) 0.57683(2) 0.02737(11) Uani 1 1 d . . . . .
Cu1 Cu 0.17216(6) -0.00044(11) 0.51280(5) 0.0315(2) Uani 1 1 d . . . . .
Cu2 Cu 0.33905(6) -0.00632(11) 0.51221(5) 0.0275(2) Uani 1 1 d . . . . .
N3 N 0.4191(3) 0.6488(4) 0.3849(2) 0.0292(11) Uani 1 1 d G . . . .
C11 C 0.4810(3) 0.5306(5) 0.3849(2) 0.0382(16) Uani 1 1 d G . . D .
H11 H 0.532287 0.547133 0.368061 0.046 Uiso 1 1 calc R U . . .
C12 C 0.4679(3) 0.3884(4) 0.4097(3) 0.0394(16) Uani 1 1 d G . . D .
H12 H 0.510216 0.307646 0.409803 0.047 Uiso 1 1 calc R U . . .
C13 C 0.3929(3) 0.3643(4) 0.4344(2) 0.0366(15) Uani 1 1 d G . . D .
H13 H 0.383929 0.267038 0.451389 0.044 Uiso 1 1 calc R U . . .
C14 C 0.3310(3) 0.4824(5) 0.4343(3) 0.0467(19) Uani 1 1 d G . . D .
H14 H 0.279713 0.465917 0.451233 0.056 Uiso 1 1 calc R U . . .
C15 C 0.3441(3) 0.6247(4) 0.4096(2) 0.0403(17) Uani 1 1 d G . . D .
H15 H 0.301783 0.705406 0.409492 0.048 Uiso 1 1 calc R U . . .
C1A C 0.0402(4) -0.0007(6) 0.5038(3) 0.0281(13) Uani 0.5 1 d . . P A 1
N1A N 0.4634(4) -0.0024(6) 0.5036(3) 0.0218(11) Uani 0.5 1 d . . P B 1
N2A N 0.0369(12) 0.1543(15) 0.1216(10) 0.024(3) Uani 0.55(3) 1 d G . P C 1
C2A C 0.0989(9) 0.032(2) 0.1448(8) 0.031(4) Uani 0.55(3) 1 d G . P C 1
H2A H 0.161693 0.048819 0.176409 0.037 Uiso 0.55(3) 1 calc R U P C 1
C3A C 0.0689(12) -0.1136(16) 0.1217(11) 0.041(5) Uani 0.55(3) 1 d G . P C 1
H3A H 0.111243 -0.196947 0.137506 0.049 Uiso 0.55(3) 1 calc R U P C 1
C4A C -0.0231(14) -0.1377(16) 0.0753(14) 0.037(5) Uani 0.55(3) 1 d G . P C 1
H4A H -0.043547 -0.237466 0.059551 0.045 Uiso 0.55(3) 1 calc R U P C 1
C5A C -0.0850(12) -0.016(2) 0.0521(13) 0.036(5) Uani 0.55(3) 1 d G . P C 1
H5A H -0.147887 -0.032218 0.020499 0.043 Uiso 0.55(3) 1 calc R U P C 1
C6A C -0.0551(12) 0.1302(18) 0.0753(12) 0.034(5) Uani 0.55(3) 1 d G . P C 1
H6A H -0.097439 0.213550 0.059402 0.041 Uiso 0.55(3) 1 calc R U P C 1
C7A C 0.0704(12) 0.3048(19) 0.1518(8) 0.026(3) Uani 0.55(3) 1 d . . P C 1
H7AA H 0.029319 0.385195 0.122728 0.031 Uiso 0.55(3) 1 calc R U P C 1
H7AB H 0.136655 0.321938 0.153059 0.031 Uiso 0.55(3) 1 calc R U P C 1
C8A C 0.0667(15) 0.311(3) 0.2232(14) 0.032(4) Uani 0.55(3) 1 d . . P C 1
H8AA H 0.113931 0.239878 0.253691 0.039 Uiso 0.55(3) 1 calc R U P C 1
H8AB H 0.002445 0.280819 0.222602 0.039 Uiso 0.55(3) 1 calc R U P C 1
C9A C 0.091(2) 0.488(3) 0.2546(14) 0.061(6) Uani 0.55(3) 1 d . . P C 1
H9AA H 0.041937 0.559629 0.225767 0.073 Uiso 0.55(3) 1 calc R U P C 1
H9AB H 0.090570 0.492608 0.303025 0.073 Uiso 0.55(3) 1 calc R U P C 1
C10A C 0.1894(16) 0.531(3) 0.2527(10) 0.076(7) Uani 0.55(3) 1 d . . P C 1
H10A H 0.234892 0.537428 0.300337 0.113 Uiso 0.55(3) 1 calc R U P C 1
H10B H 0.185745 0.629113 0.229437 0.113 Uiso 0.55(3) 1 calc R U P C 1
H10C H 0.210837 0.453037 0.226926 0.113 Uiso 0.55(3) 1 calc R U P C 1
C16A C 0.431(3) 0.794(4) 0.3537(11) 0.034(5) Uani 0.70(2) 1 d . . P D 1
H16A H 0.498944 0.804633 0.358341 0.041 Uiso 0.70(2) 1 calc R U P D 1
H16B H 0.415400 0.876495 0.380802 0.041 Uiso 0.70(2) 1 calc R U P D 1
C17A C 0.3717(9) 0.813(2) 0.2790(9) 0.028(3) Uani 0.70(2) 1 d . . P D 1
H17A H 0.303541 0.802149 0.274089 0.034 Uiso 0.70(2) 1 calc R U P D 1
H17B H 0.387451 0.731222 0.251607 0.034 Uiso 0.70(2) 1 calc R U P D 1
C18A C 0.3852(14) 0.964(2) 0.2487(9) 0.058(5) Uani 0.70(2) 1 d . . P D 1
H18A H 0.441382 0.952580 0.233672 0.069 Uiso 0.70(2) 1 calc R U P D 1
H18B H 0.329268 0.977732 0.205647 0.069 Uiso 0.70(2) 1 calc R U P D 1
C19A C 0.3968(11) 1.0966(14) 0.2832(6) 0.051(4) Uani 0.70(2) 1 d . . P D 1
H19A H 0.339513 1.118858 0.294792 0.077 Uiso 0.70(2) 1 calc R U P D 1
H19B H 0.407267 1.177969 0.253892 0.077 Uiso 0.70(2) 1 calc R U P D 1
H19C H 0.452172 1.089430 0.326185 0.077 Uiso 0.70(2) 1 calc R U P D 1
N1B N 0.0402(4) -0.0007(6) 0.5038(3) 0.0281(13) Uani 0.5 1 d . . P A 2
C1B C 0.4634(4) -0.0024(6) 0.5036(3) 0.0218(11) Uani 0.5 1 d . . P B 2
N2B N 0.0576(15) 0.117(2) 0.1338(10) 0.023(4) Uani 0.45(3) 1 d G . P C 2
C2B C 0.0975(13) -0.027(3) 0.1487(11) 0.046(6) Uani 0.45(3) 1 d G . P C 2
H2B H 0.158499 -0.039318 0.183560 0.055 Uiso 0.45(3) 1 calc R U P C 2
C3B C 0.0483(19) -0.152(2) 0.1127(15) 0.052(7) Uani 0.45(3) 1 d G . P C 2
H3B H 0.075640 -0.250519 0.122928 0.062 Uiso 0.45(3) 1 calc R U P C 2
C4B C -0.041(2) -0.134(2) 0.0618(16) 0.040(6) Uani 0.45(3) 1 d G . P C 2
H4B H -0.074515 -0.219361 0.037140 0.048 Uiso 0.45(3) 1 calc R U P C 2
C5B C -0.0809(15) 0.010(3) 0.0468(15) 0.027(5) Uani 0.45(3) 1 d G . P C 2
H5B H -0.141811 0.023000 0.011984 0.033 Uiso 0.45(3) 1 calc R U P C 2
C6B C -0.0316(16) 0.1358(19) 0.0828(13) 0.017(4) Uani 0.45(3) 1 d G . P C 2
H6B H -0.058953 0.234204 0.072616 0.020 Uiso 0.45(3) 1 calc R U P C 2
C7B C 0.1036(18) 0.261(3) 0.1689(11) 0.034(5) Uani 0.45(3) 1 d . . P C 2
H7BA H 0.091258 0.342585 0.133716 0.041 Uiso 0.45(3) 1 calc R U P C 2
H7BB H 0.173516 0.245217 0.188733 0.041 Uiso 0.45(3) 1 calc R U P C 2
C8B C 0.066(3) 0.311(6) 0.228(2) 0.069(11) Uani 0.45(3) 1 d . . P C 2
H8BA H -0.002103 0.341119 0.207952 0.083 Uiso 0.45(3) 1 calc R U P C 2
H8BB H 0.070588 0.225441 0.260624 0.083 Uiso 0.45(3) 1 calc R U P C 2
C9B C 0.122(2) 0.437(4) 0.266(2) 0.061(8) Uani 0.45(3) 1 d . . P C 2
H9BA H 0.100261 0.459986 0.305379 0.073 Uiso 0.45(3) 1 calc R U P C 2
H9BB H 0.188848 0.402924 0.285287 0.073 Uiso 0.45(3) 1 calc R U P C 2
C10B C 0.1216(19) 0.574(3) 0.2308(17) 0.072(9) Uani 0.45(3) 1 d . . P C 2
H10D H 0.161329 0.564072 0.201453 0.108 Uiso 0.45(3) 1 calc R U P C 2
H10E H 0.147245 0.655319 0.265047 0.108 Uiso 0.45(3) 1 calc R U P C 2
H10F H 0.056076 0.599682 0.201667 0.108 Uiso 0.45(3) 1 calc R U P C 2
C16B C 0.433(7) 0.806(10) 0.364(3) 0.039(10) Uani 0.30(2) 1 d . . P D 2
H16C H 0.501306 0.835641 0.384523 0.047 Uiso 0.30(2) 1 calc R U P D 2
H16D H 0.394134 0.878406 0.379440 0.047 Uiso 0.30(2) 1 calc R U P D 2
C17B C 0.401(4) 0.804(6) 0.281(2) 0.060(11) Uani 0.30(2) 1 d . . P D 2
H17C H 0.430275 0.715437 0.266416 0.072 Uiso 0.30(2) 1 calc R U P D 2
H17D H 0.331037 0.793364 0.261544 0.072 Uiso 0.30(2) 1 calc R U P D 2
C18B C 0.431(4) 0.947(5) 0.2545(19) 0.060(11) Uani 0.30(2) 1 d . . P D 2
H18C H 0.465572 0.908866 0.224006 0.072 Uiso 0.30(2) 1 calc R U P D 2
H18D H 0.370080 0.987772 0.222345 0.072 Uiso 0.30(2) 1 calc R U P D 2
C19B C 0.472(2) 1.052(3) 0.2788(12) 0.044(9) Uani 0.30(2) 1 d . . P D 2
H19D H 0.510957 1.030766 0.327385 0.066 Uiso 0.30(2) 1 calc R U P D 2
H19E H 0.427659 1.134623 0.277149 0.066 Uiso 0.30(2) 1 calc R U P D 2
H19F H 0.514271 1.081494 0.252970 0.066 Uiso 0.30(2) 1 calc R U P D 2


_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 Cu1 2.6741(10) . ?
I1 Cu2 2.6782(10) . ?
I2 Cu1 2.7750(11) . ?
I2 Cu2 2.7866(10) . ?
I3 Cu1 2.6922(10) . ?
I3 Cu2 2.7645(10) . ?
Cu1 N1B 1.911(6) . ?
Cu1 C1A 1.911(6) . ?
Cu1 Cu2 2.4906(12) . ?
Cu2 C1B 1.920(5) . ?
Cu2 N1A 1.920(5) . ?
N3 C11 1.3900 . ?
N3 C15 1.3900 . ?
N3 C16A 1.46(3) . ?
N3 C16B 1.48(8) . ?
C11 C12 1.3900 . ?
C11 H11 0.9500 . ?
C12 C13 1.3900 . ?
C12 H12 0.9500 . ?
C13 C14 1.3900 . ?
C13 H13 0.9500 . ?
C14 C15 1.3900 . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C1A C1A 1.154(11) 3_556 ?
N1A N1A 1.149(10) 3_656 ?
N2A C2A 1.3900 . ?
N2A C6A 1.3900 . ?
N2A C7A 1.476(16) . ?
C2A C3A 1.3900 . ?
C2A H2A 0.9500 . ?
C3A C4A 1.3900 . ?
C3A H3A 0.9500 . ?
C4A C5A 1.3900 . ?
C4A H4A 0.9500 . ?
C5A C6A 1.3900 . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A C8A 1.48(3) . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C8A C9A 1.68(4) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C9A C10A 1.53(4) . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A H10C 0.9800 . ?
C16A C17A 1.49(2) . ?
C16A H16A 0.9900 . ?
C16A H16B 0.9900 . ?
C17A C18A 1.509(19) . ?
C17A H17A 0.9900 . ?
C17A H17B 0.9900 . ?
C18A C19A 1.34(2) . ?
C18A H18A 0.9900 . ?
C18A H18B 0.9900 . ?
C19A H19A 0.9800 . ?
C19A H19B 0.9800 . ?
C19A H19C 0.9800 . ?
N2B C2B 1.3900 . ?
N2B C6B 1.3900 . ?
N2B C7B 1.50(2) . ?
C2B C3B 1.3900 . ?
C2B H2B 0.9500 . ?
C3B C4B 1.3900 . ?
C3B H3B 0.9500 . ?
C4B C5B 1.3900 . ?
C4B H4B 0.9500 . ?
C5B C6B 1.3900 . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B C8B 1.56(5) . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C8B C9B 1.44(6) . ?
C8B H8BA 0.9900 . ?
C8B H8BB 0.9900 . ?
C9B C10B 1.40(5) . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?
C16B C17B 1.58(7) . ?
C16B H16C 0.9900 . ?
C16B H16D 0.9900 . ?
C17B C18B 1.50(5) . ?
C17B H17C 0.9900 . ?
C17B H17D 0.9900 . ?
C18B C19B 1.13(4) . ?
C18B H18C 0.9900 . ?
C18B H18D 0.9900 . ?
C19B H19D 0.9800 . ?
C19B H19E 0.9800 . ?
C19B H19F 0.9800 . ?

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
Cu1 I1 Cu2 55.46(3) . . ?
Cu1 I2 Cu2 53.21(3) . . ?
Cu1 I3 Cu2 54.29(3) . . ?
N1B Cu1 Cu2 174.4(2) . . ?
C1A Cu1 Cu2 174.4(2) . . ?
N1B Cu1 I1 119.07(17) . . ?
C1A Cu1 I1 119.07(17) . . ?
Cu2 Cu1 I1 62.35(3) . . ?
N1B Cu1 I3 119.45(18) . . ?
C1A Cu1 I3 119.45(18) . . ?
Cu2 Cu1 I3 64.33(3) . . ?
I1 Cu1 I3 101.57(3) . . ?
N1B Cu1 I2 110.97(19) . . ?
C1A Cu1 I2 110.97(19) . . ?
Cu2 Cu1 I2 63.64(3) . . ?
I1 Cu1 I2 101.98(3) . . ?
I3 Cu1 I2 101.06(3) . . ?
C1B Cu2 Cu1 174.80(17) . . ?
N1A Cu2 Cu1 174.80(17) . . ?
C1B Cu2 I1 122.01(17) . . ?
N1A Cu2 I1 122.01(17) . . ?
Cu1 Cu2 I1 62.18(3) . . ?
C1B Cu2 I3 118.97(15) . . ?
N1A Cu2 I3 118.97(15) . . ?
Cu1 Cu2 I3 61.37(3) . . ?
I1 Cu2 I3 99.60(3) . . ?
C1B Cu2 I2 112.04(16) . . ?
N1A Cu2 I2 112.04(16) . . ?
Cu1 Cu2 I2 63.16(3) . . ?
I1 Cu2 I2 101.57(3) . . ?
I3 Cu2 I2 98.99(3) . . ?
C11 N3 C15 120.0 . . ?
C11 N3 C16A 118.4(15) . . ?
C15 N3 C16A 121.4(15) . . ?
C11 N3 C16B 123(4) . . ?
C15 N3 C16B 117(4) . . ?
C12 C11 N3 120.0 . . ?
C12 C11 H11 120.0 . . ?
N3 C11 H11 120.0 . . ?
C13 C12 C11 120.0 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.0 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C15 120.0 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 N3 120.0 . . ?
C14 C15 H15 120.0 . . ?
N3 C15 H15 120.0 . . ?
C1A C1A Cu1 177.8(8) 3_556 . ?
N1A N1A Cu2 177.9(7) 3_656 . ?
C2A N2A C6A 120.0 . . ?
C2A N2A C7A 117.4(10) . . ?
C6A N2A C7A 122.4(10) . . ?
C3A C2A N2A 120.0 . . ?
C3A C2A H2A 120.0 . . ?
N2A C2A H2A 120.0 . . ?
C4A C3A C2A 120.0 . . ?
C4A C3A H3A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C3A C4A C5A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C4A C5A C6A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C5A C6A N2A 120.0 . . ?
C5A C6A H6A 120.0 . . ?
N2A C6A H6A 120.0 . . ?
N2A C7A C8A 109.0(18) . . ?
N2A C7A H7AA 109.9 . . ?
C8A C7A H7AA 109.9 . . ?
N2A C7A H7AB 109.9 . . ?
C8A C7A H7AB 109.9 . . ?
H7AA C7A H7AB 108.3 . . ?
C7A C8A C9A 110(2) . . ?
C7A C8A H8AA 109.7 . . ?
C9A C8A H8AA 109.7 . . ?
C7A C8A H8AB 109.7 . . ?
C9A C8A H8AB 109.7 . . ?
H8AA C8A H8AB 108.2 . . ?
C10A C9A C8A 107(2) . . ?
C10A C9A H9AA 110.2 . . ?
C8A C9A H9AA 110.2 . . ?
C10A C9A H9AB 110.2 . . ?
C8A C9A H9AB 110.2 . . ?
H9AA C9A H9AB 108.5 . . ?
C9A C10A H10A 109.5 . . ?
C9A C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
C9A C10A H10C 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
N3 C16A C17A 115.5(19) . . ?
N3 C16A H16A 108.4 . . ?
C17A C16A H16A 108.4 . . ?
N3 C16A H16B 108.4 . . ?
C17A C16A H16B 108.4 . . ?
H16A C16A H16B 107.5 . . ?
C16A C17A C18A 114.1(16) . . ?
C16A C17A H17A 108.7 . . ?
C18A C17A H17A 108.7 . . ?
C16A C17A H17B 108.7 . . ?
C18A C17A H17B 108.7 . . ?
H17A C17A H17B 107.6 . . ?
C19A C18A C17A 124.1(14) . . ?
C19A C18A H18A 106.3 . . ?
C17A C18A H18A 106.3 . . ?
C19A C18A H18B 106.3 . . ?
C17A C18A H18B 106.3 . . ?
H18A C18A H18B 106.4 . . ?
C18A C19A H19A 109.5 . . ?
C18A C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
C18A C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C2B N2B C6B 120.0 . . ?
C2B N2B C7B 124.9(13) . . ?
C6B N2B C7B 115.1(13) . . ?
N2B C2B C3B 120.0 . . ?
N2B C2B H2B 120.0 . . ?
C3B C2B H2B 120.0 . . ?
C4B C3B C2B 120.0 . . ?
C4B C3B H3B 120.0 . . ?
C2B C3B H3B 120.0 . . ?
C5B C4B C3B 120.0 . . ?
C5B C4B H4B 120.0 . . ?
C3B C4B H4B 120.0 . . ?
C4B C5B C6B 120.0 . . ?
C4B C5B H5B 120.0 . . ?
C6B C5B H5B 120.0 . . ?
C5B C6B N2B 120.0 . . ?
C5B C6B H6B 120.0 . . ?
N2B C6B H6B 120.0 . . ?
N2B C7B C8B 113(2) . . ?
N2B C7B H7BA 109.1 . . ?
C8B C7B H7BA 109.1 . . ?
N2B C7B H7BB 109.1 . . ?
C8B C7B H7BB 109.1 . . ?
H7BA C7B H7BB 107.8 . . ?
C9B C8B C7B 109(3) . . ?
C9B C8B H8BA 109.8 . . ?
C7B C8B H8BA 109.8 . . ?
C9B C8B H8BB 109.8 . . ?
C7B C8B H8BB 109.8 . . ?
H8BA C8B H8BB 108.2 . . ?
C10B C9B C8B 120(4) . . ?
C10B C9B H9BA 107.4 . . ?
C8B C9B H9BA 107.4 . . ?
C10B C9B H9BB 107.4 . . ?
C8B C9B H9BB 107.4 . . ?
H9BA C9B H9BB 106.9 . . ?
C9B C10B H10D 109.5 . . ?
C9B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
C9B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
N3 C16B C17B 106(5) . . ?
N3 C16B H16C 110.5 . . ?
C17B C16B H16C 110.5 . . ?
N3 C16B H16D 110.5 . . ?
C17B C16B H16D 110.5 . . ?
H16C C16B H16D 108.7 . . ?
C18B C17B C16B 111(4) . . ?
C18B C17B H17C 109.4 . . ?
C16B C17B H17C 109.4 . . ?
C18B C17B H17D 109.4 . . ?
C16B C17B H17D 109.4 . . ?
H17C C17B H17D 108.0 . . ?
C19B C18B C17B 135(3) . . ?
C19B C18B H18C 103.3 . . ?
C17B C18B H18C 103.3 . . ?
C19B C18B H18D 103.3 . . ?
C17B C18B H18D 103.3 . . ?
H18C C18B H18D 105.2 . . ?
C18B C19B H19D 109.5 . . ?
C18B C19B H19E 109.5 . . ?
H19D C19B H19E 109.5 . . ?
C18B C19B H19F 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 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
C15 N3 C11 C12 0.0 . . . . ?
C16A N3 C11 C12 -175.6(11) . . . . ?
C16B N3 C11 C12 176(3) . . . . ?
N3 C11 C12 C13 0.0 . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C13 C14 C15 N3 0.0 . . . . ?
C11 N3 C15 C14 0.0 . . . . ?
C16A N3 C15 C14 175.5(11) . . . . ?
C16B N3 C15 C14 -176(3) . . . . ?
C6A N2A C2A C3A 0.0 . . . . ?
C7A N2A C2A C3A 175.7(16) . . . . ?
N2A C2A C3A C4A 0.0 . . . . ?
C2A C3A C4A C5A 0.0 . . . . ?
C3A C4A C5A C6A 0.0 . . . . ?
C4A C5A C6A N2A 0.0 . . . . ?
C2A N2A C6A C5A 0.0 . . . . ?
C7A N2A C6A C5A -175.5(17) . . . . ?
C2A N2A C7A C8A -75.3(17) . . . . ?
C6A N2A C7A C8A 100.3(14) . . . . ?
N2A C7A C8A C9A -172.7(14) . . . . ?
C7A C8A C9A C10A -58(2) . . . . ?
C11 N3 C16A C17A 93(3) . . . . ?
C15 N3 C16A C17A -82(2) . . . . ?
N3 C16A C17A C18A 180(2) . . . . ?
C16A C17A C18A C19A -39(2) . . . . ?
C6B N2B C2B C3B 0.0 . . . . ?
C7B N2B C2B C3B -180(2) . . . . ?
N2B C2B C3B C4B 0.0 . . . . ?
C2B C3B C4B C5B 0.0 . . . . ?
C3B C4B C5B C6B 0.0 . . . . ?
C4B C5B C6B N2B 0.0 . . . . ?
C2B N2B C6B C5B 0.0 . . . . ?
C7B N2B C6B C5B 179.9(19) . . . . ?
C2B N2B C7B C8B -98(3) . . . . ?
C6B N2B C7B C8B 82(3) . . . . ?
N2B C7B C8B C9B 172(3) . . . . ?
C7B C8B C9B C10B 63(5) . . . . ?
C11 N3 C16B C17B 76(6) . . . . ?
C15 N3 C16B C17B -108(5) . . . . ?
N3 C16B C17B C18B -168(5) . . . . ?
C16B C17B C18B C19B 2(9) . . . . ?

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
_geom_hbond_publ_flag
C3A^a H3A^a I1 0.95 3.28 3.851(18) 120.8 4 yes
C5A^a H5A^a I3 0.95 3.09 3.904(13) 144.7 2_545 yes
C6A^a H6A^a I1 0.95 3.15 3.856(14) 132.7 2 yes
C7A^a H7AB^a I3 0.99 3.13 3.982(16) 145.5 4_565 yes
C8A^a H8AA^a I2 0.99 3.23 4.15(2) 154.3 . yes
C16A^a H16A^a I3 0.99 3.07 4.00(4) 157.6 3_666 yes
C16A^a H16B^a N1A^a 0.99 2.59 3.44(3) 143.5 1_565 yes
C5B^b H5B^b I1 0.95 3.05 3.847(19) 142.9 2 yes
C7B^b H7BB^b I3 0.99 3.24 3.76(2) 114.7 4_565 yes
C8B^b H8BA^b I2 0.99 3.18 4.14(5) 162.3 2 yes
C8B^b H8BB^b I2 0.99 3.19 4.08(5) 150.9 . yes
C16B^b H16C^b I3 0.99 3.09 3.98(10) 151.2 3_666 yes
C16B^b H16D^b I2 0.99 3.22 4.12(10) 152.8 1_565 yes
C11 H11 I3 0.95 3.23 3.916(4) 131.1 3_666 yes
C12 H12 I1 0.95 3.07 3.869(3) 142.7 3_656 yes
C14 H14 I3 0.95 3.26 3.892(4) 125.4 . yes
C15 H15 I2 0.95 3.06 3.982(3) 163.7 1_565 yes

_refine_diff_density_max         0.594
_refine_diff_density_min         -0.788
_refine_diff_density_rms         0.123


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: tetrahydrofuran'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_RDP697_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1964376'
loop_
_audit_author_name
_audit_author_address
'Robert Pike'
;College of William and Mary
United States of America
;
_audit_update_record             
;
2019-11-07 deposited with the CCDC.	2019-12-27 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT315_mo_RDP697_0m_a      
;
PROBLEM: Singly Bonded Carbon Detected (H-atoms Missing).        C1A Check
RESPONSE: This dangling carbon is an artifact of a symmetrically disordered bridging cyano group. The carbon/nitrogen is actually bonded to a crystallographically equivalent carbon/nitrogen across an inversion centre.
;
# Added during the CSD deposition process: Thursday 07 November 2019 03:50 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/5
_chemical_name_systematic        
'N-Propylpyridinium catena-mu2-cyanotri-mu2-iododicopper(I)'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C8 H12 N), C Cu2 I3 N'
_chemical_formula_sum            'C17 H24 Cu2 I3 N3'
_chemical_formula_weight         778.17

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.8148(14)
_cell_length_b                   14.4485(19)
_cell_length_c                   14.7668(19)
_cell_angle_alpha                90
_cell_angle_beta                 102.129(2)
_cell_angle_gamma                90
_cell_volume                     2255.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9967
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      26.24

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.291
_exptl_crystal_F_000             1456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.533
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.051
_exptl_absorpt_coefficient_mu    5.997
_shelx_estimated_absorpt_T_min   0.142
_shelx_estimated_absorpt_T_max   0.750
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.5004
_exptl_absorpt_correction_T_max  0.9123
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω and ψ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34376
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.994
_diffrn_reflns_theta_max         26.320
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4557
_reflns_number_gt                3879
_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINTPLUS (Bruker AXS, 2004)'
_computing_data_reduction        SAINTPLUS
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/5 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXLE (Hubschle, 2011)'
_computing_publication_material  'Mercury 3.7 (CCDC, 2016)'
_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)+(0.0147P)²+1.3252P] 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         4557
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0185
_refine_ls_wR_factor_ref         0.0376
_refine_ls_wR_factor_gt          0.0349
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.002
_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
I1 I 0.63981(2) 0.62228(2) 0.28073(2) 0.01374(5) Uani 1 1 d . . . . .
I2 I 0.25631(2) 0.54063(2) 0.21044(2) 0.01457(5) Uani 1 1 d . . . . .
I3 I 0.54057(2) 0.33501(2) 0.24916(2) 0.01483(5) Uani 1 1 d . . . . .
Cu1 Cu 0.49202(4) 0.50588(3) 0.16736(2) 0.01865(9) Uani 1 1 d . . . . .
Cu2 Cu 0.46383(4) 0.48611(3) 0.32875(2) 0.01907(9) Uani 1 1 d . . . . .
N1A N 0.4894(3) 0.49545(19) 0.46010(17) 0.0139(6) Uani 0.5 1 d . . P A 1
C1A C 0.4965(3) 0.50177(19) 0.03826(18) 0.0156(6) Uani 0.5 1 d . . P B 1
N1B N 0.4965(3) 0.50177(19) 0.03826(18) 0.0156(6) Uani 0.5 1 d . . P B 2
C1B C 0.4894(3) 0.49545(19) 0.46010(17) 0.0139(6) Uani 0.5 1 d . . P A 2
N2 N -0.0268(2) 0.31084(16) 0.49352(16) 0.0128(5) Uani 1 1 d . . . C 2
C2 C -0.1277(3) 0.3380(2) 0.4294(2) 0.0197(7) Uani 1 1 d . . . C 2
H2 H -0.1495 0.3060 0.3721 0.024 Uiso 1 1 calc R U . C 2
C3 C -0.1994(3) 0.4120(2) 0.4463(2) 0.0234(8) Uani 1 1 d . . . C 2
H3 H -0.2697 0.4320 0.4005 0.028 Uiso 1 1 calc R U . C 2
C4 C -0.1682(3) 0.4573(2) 0.5309(2) 0.0228(7) Uani 1 1 d . . . C 2
H4 H -0.2189 0.5070 0.5445 0.027 Uiso 1 1 calc R U . C 2
C5 C -0.0637(3) 0.4296(2) 0.5947(2) 0.0189(7) Uani 1 1 d . . . C 2
H5 H -0.0404 0.4612 0.6522 0.023 Uiso 1 1 calc R U . C 2
C6 C 0.0077(3) 0.3556(2) 0.5755(2) 0.0155(7) Uani 1 1 d . . . C 2
H6 H 0.0804 0.3363 0.6195 0.019 Uiso 1 1 calc R U . C 2
C7 C 0.0503(3) 0.2294(2) 0.4766(2) 0.0191(7) Uani 1 1 d . . . C 2
H7A H 0.0010 0.1921 0.4252 0.023 Uiso 1 1 calc R U . C 2
H7AB H 0.0679 0.1901 0.5327 0.023 Uiso 1 1 calc R U . C 2
C8 C 0.1742(3) 0.2578(2) 0.4525(2) 0.0204(7) Uani 1 1 d . . . C 2
H8A H 0.2267 0.2018 0.4515 0.024 Uiso 1 1 calc R U . C 2
H8AB H 0.2200 0.2991 0.5017 0.024 Uiso 1 1 calc R U . C 2
C9 C 0.1593(3) 0.3071(2) 0.3595(2) 0.0242(8) Uani 1 1 d . . . C 2
H9A H 0.2429 0.3237 0.3488 0.036 Uiso 1 1 calc R U . C 2
H9AB H 0.1087 0.3633 0.3601 0.036 Uiso 1 1 calc R U . C 2
H9AC H 0.1167 0.2659 0.3099 0.036 Uiso 1 1 calc R U . C 2
N3 N 0.6307(2) 0.14185(17) 0.45983(17) 0.0156(6) Uani 1 1 d . . . D 2
C10 C 0.7237(3) 0.1523(2) 0.5356(2) 0.0215(7) Uani 1 1 d . . . D 2
H10 H 0.7964 0.1137 0.5441 0.026 Uiso 1 1 calc R U . D 2
C11 C 0.7143(3) 0.2181(2) 0.6005(2) 0.0225(7) Uani 1 1 d . . . D 2
H11 H 0.7800 0.2249 0.6539 0.027 Uiso 1 1 calc R U . D 2
C12 C 0.6097(3) 0.2743(2) 0.5881(2) 0.0200(7) Uani 1 1 d . . . D 2
H12 H 0.6028 0.3208 0.6322 0.024 Uiso 1 1 calc R U . D 2
C13 C 0.5146(3) 0.2620(2) 0.5104(2) 0.0195(7) Uani 1 1 d . . . D 2
H13 H 0.4412 0.2999 0.5010 0.023 Uiso 1 1 calc R U . D 2
C14 C 0.5264(3) 0.1952(2) 0.4470(2) 0.0176(7) Uani 1 1 d . . . D 2
H14 H 0.4607 0.1865 0.3938 0.021 Uiso 1 1 calc R U . D 2
C15 C 0.6442(4) 0.0707(2) 0.3890(2) 0.0291(9) Uani 1 1 d . . . D 2
H15A H 0.7322 0.0718 0.3797 0.035 Uiso 1 1 calc R U . D 2
H15B H 0.5876 0.0871 0.3294 0.035 Uiso 1 1 calc R U . D 2
C16 C 0.6133(3) -0.0254(2) 0.4156(2) 0.0199(7) Uani 1 1 d . . . D 2
H16A H 0.5248 -0.0275 0.4237 0.024 Uiso 1 1 calc R U . D 2
H16B H 0.6693 -0.0423 0.4753 0.024 Uiso 1 1 calc R U . D 2
C17 C 0.6307(3) -0.0942(2) 0.3413(2) 0.0282(8) Uani 1 1 d . . . D 2
H17A H 0.6166 -0.1571 0.3618 0.042 Uiso 1 1 calc R U . D 2
H17B H 0.7169 -0.0892 0.3306 0.042 Uiso 1 1 calc R U . D 2
H17C H 0.5699 -0.0807 0.2837 0.042 Uiso 1 1 calc R U . D 2


_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 Cu1 2.6574(5) . ?
I1 Cu2 2.9262(5) . ?
I2 Cu2 2.6575(5) . ?
I2 Cu1 2.7993(5) . ?
I3 Cu2 2.6917(5) . ?
I3 Cu1 2.7501(5) . ?
Cu1 N1B 1.918(3) . ?
Cu1 C1A 1.918(3) . ?
Cu1 Cu2 2.4818(6) . ?
Cu2 C1B 1.906(2) . ?
Cu2 N1A 1.906(2) . ?
N1A N1A 1.160(5) 3_666 ?
C1A C1A 1.150(5) 3_665 ?
N1B N1B 1.150(5) 3_665 ?
C1B C1B 1.160(5) 3_666 ?
N2 C2 1.345(4) . ?
N2 C6 1.354(4) . ?
N2 C7 1.493(4) . ?
C2 C3 1.374(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.370(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.514(4) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 C9 1.524(4) . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9AB 0.9800 . ?
C9 H9AC 0.9800 . ?
N3 C14 1.347(4) . ?
N3 C10 1.347(4) . ?
N3 C15 1.495(4) . ?
C10 C11 1.368(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.374(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.381(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.370(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.499(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.522(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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
Cu1 I1 Cu2 52.511(13) . . ?
Cu2 I2 Cu1 54.029(14) . . ?
Cu2 I3 Cu1 54.252(14) . . ?
N1B Cu1 Cu2 169.96(8) . . ?
C1A Cu1 Cu2 169.96(8) . . ?
N1B Cu1 I1 120.55(8) . . ?
C1A Cu1 I1 120.55(8) . . ?
Cu2 Cu1 I1 69.321(15) . . ?
N1B Cu1 I3 111.50(8) . . ?
C1A Cu1 I3 111.50(8) . . ?
Cu2 Cu1 I3 61.674(13) . . ?
I1 Cu1 I3 104.914(16) . . ?
N1B Cu1 I2 116.47(8) . . ?
C1A Cu1 I2 116.47(8) . . ?
Cu2 Cu1 I2 60.066(13) . . ?
I1 Cu1 I2 101.492(15) . . ?
I3 Cu1 I2 99.214(13) . . ?
C1B Cu2 Cu1 161.52(9) . . ?
N1A Cu2 Cu1 161.52(9) . . ?
C1B Cu2 I2 124.75(8) . . ?
N1A Cu2 I2 124.75(8) . . ?
Cu1 Cu2 I2 65.905(15) . . ?
C1B Cu2 I3 120.64(8) . . ?
N1A Cu2 I3 120.64(8) . . ?
Cu1 Cu2 I3 64.074(14) . . ?
I2 Cu2 I3 104.398(15) . . ?
C1B Cu2 I1 103.67(8) . . ?
N1A Cu2 I1 103.67(8) . . ?
Cu1 Cu2 I1 58.169(13) . . ?
I2 Cu2 I1 98.270(15) . . ?
I3 Cu2 I1 99.420(15) . . ?
N1A N1A Cu2 176.1(4) 3_666 . ?
C1A C1A Cu1 177.6(4) 3_665 . ?
N1B N1B Cu1 177.6(4) 3_665 . ?
C1B C1B Cu2 176.1(4) 3_666 . ?
C2 N2 C6 121.4(3) . . ?
C2 N2 C7 120.7(2) . . ?
C6 N2 C7 117.9(2) . . ?
N2 C2 C3 120.3(3) . . ?
N2 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 119.4(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
N2 C6 C5 119.4(3) . . ?
N2 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
N2 C7 C8 112.3(2) . . ?
N2 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
N2 C7 H7AB 109.1 . . ?
C8 C7 H7AB 109.1 . . ?
H7A C7 H7AB 107.9 . . ?
C7 C8 C9 114.0(3) . . ?
C7 C8 H8A 108.8 . . ?
C9 C8 H8A 108.8 . . ?
C7 C8 H8AB 108.8 . . ?
C9 C8 H8AB 108.8 . . ?
H8A C8 H8AB 107.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9AB 109.5 . . ?
H9A C9 H9AB 109.5 . . ?
C8 C9 H9AC 109.5 . . ?
H9A C9 H9AC 109.5 . . ?
H9AB C9 H9AC 109.5 . . ?
C14 N3 C10 120.7(3) . . ?
C14 N3 C15 119.8(3) . . ?
C10 N3 C15 119.5(3) . . ?
N3 C10 C11 120.5(3) . . ?
N3 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 119.9(3) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C13 118.9(3) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
N3 C14 C13 120.2(3) . . ?
N3 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
N3 C15 C16 113.2(3) . . ?
N3 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
N3 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 C17 110.4(3) . . ?
C15 C16 H16A 109.6 . . ?
C17 C16 H16A 109.6 . . ?
C15 C16 H16B 109.6 . . ?
C17 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C6 N2 C2 C3 -0.7(4) . . . . ?
C7 N2 C2 C3 178.8(3) . . . . ?
N2 C2 C3 C4 -1.3(5) . . . . ?
C2 C3 C4 C5 2.4(5) . . . . ?
C3 C4 C5 C6 -1.7(5) . . . . ?
C2 N2 C6 C5 1.4(4) . . . . ?
C7 N2 C6 C5 -178.1(3) . . . . ?
C4 C5 C6 N2 -0.2(4) . . . . ?
C2 N2 C7 C8 103.8(3) . . . . ?
C6 N2 C7 C8 -76.8(3) . . . . ?
N2 C7 C8 C9 -67.1(3) . . . . ?
C14 N3 C10 C11 -0.7(5) . . . . ?
C15 N3 C10 C11 178.9(3) . . . . ?
N3 C10 C11 C12 -0.3(5) . . . . ?
C10 C11 C12 C13 1.0(5) . . . . ?
C11 C12 C13 C14 -0.6(5) . . . . ?
C10 N3 C14 C13 1.1(4) . . . . ?
C15 N3 C14 C13 -178.5(3) . . . . ?
C12 C13 C14 N3 -0.4(5) . . . . ?
C14 N3 C15 C16 -100.5(3) . . . . ?
C10 N3 C15 C16 80.0(4) . . . . ?
N3 C15 C16 C17 -179.2(3) . . . . ?

_refine_diff_density_max         0.572
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.111

_shelxl_version_number           2014/5


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_C2onc_a
_database_code_depnum_ccdc_archive 'CCDC 1964374'
loop_
_audit_author_name
_audit_author_address
'Robert Pike'
;College of William and Mary
United States of America
;
_audit_update_record             
;
2019-11-07 deposited with the CCDC.	2019-12-27 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT315_C2onc_a             
;
PROBLEM: Singly Bonded Carbon Detected (H-atoms Missing).         C1 Check
RESPONSE: This dangling carbon is an artifact of a symmetrically disordered bridging cyano group. The carbon/nitrogen is actually bonded to a crystallographically equivalent carbon/nitrogen across an inversion centre.
;
# Added during the CSD deposition process: Thursday 07 November 2019 03:50 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/5
_chemical_name_systematic        
'N-Ethylpyridinium catena-mu2-cyanotri-mu2-iododicopper(I)'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C7 H10 N), C Cu2 I3 N'
_chemical_formula_sum            'C15 H20 Cu2 I3 N3'
_chemical_formula_weight         750.12

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'
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.3925(7)
_cell_length_b                   16.2544(8)
_cell_length_c                   9.1907(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.1840(10)
_cell_angle_gamma                90
_cell_volume                     2075.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8045
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      26.19

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.401
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.056
_exptl_absorpt_coefficient_mu    6.514
_shelx_estimated_absorpt_T_min   0.215
_shelx_estimated_absorpt_T_max   0.712
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.3937
_exptl_absorpt_correction_T_max  0.7984
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_special_details           
; 
 ? 
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω and ψ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16145
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.929
_diffrn_reflns_theta_max         26.203
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2090
_reflns_number_gt                1922
_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_cell_refinement       'SAINTPLUS (Bruker AXS, 2004)'
_computing_data_reduction        SAINTPLUS
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/5 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXLE (Hubschle, 2011)'
_computing_publication_material  'Mercury 3.7 (CCDC, 2016)'
_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)+(0.0080P)²+6.5315P] 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         2090
_refine_ls_number_parameters     106
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0175
_refine_ls_R_factor_gt           0.0147
_refine_ls_wR_factor_ref         0.0315
_refine_ls_wR_factor_gt          0.0306
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.5000 0.10372(2) 0.2500 0.01410(6) Uani 1 2 d S T P A .
I2 I 0.44587(2) 0.32946(2) 0.44004(2) 0.01254(5) Uani 1 1 d . . . . .
Cu1 Cu 0.58189(2) 0.25419(2) 0.33786(4) 0.01590(8) Uani 1 1 d . . . . .
N1 N 0.71088(16) 0.25124(14) 0.4617(3) 0.0136(5) Uani 0.5 1 d . . P A 1
C1 C 0.71088(16) 0.25124(14) 0.4617(3) 0.0136(5) Uani 0.5 1 d . . P A 2
N2 N 0.19887(15) 0.41678(13) 0.5269(2) 0.0129(4) Uani 1 1 d . . . . .
C2 C 0.23989(18) 0.36580(16) 0.6416(3) 0.0159(5) Uani 1 1 d . . . . .
H2 H 0.2118 0.3136 0.6491 0.019 Uiso 1 1 calc R U . . .
C3 C 0.32202(19) 0.38891(17) 0.7475(3) 0.0172(5) Uani 1 1 d . . . . .
H3 H 0.3512 0.3526 0.8274 0.021 Uiso 1 1 calc R U . . .
C4 C 0.36200(19) 0.46534(17) 0.7372(3) 0.0184(6) Uani 1 1 d . . . . .
H4 H 0.4190 0.4820 0.8095 0.022 Uiso 1 1 calc R U . . .
C5 C 0.31773(19) 0.51746(16) 0.6199(3) 0.0193(6) Uani 1 1 d . . . . .
H5 H 0.3437 0.5705 0.6121 0.023 Uiso 1 1 calc R U . . .
C6 C 0.23627(19) 0.49200(16) 0.5153(3) 0.0171(5) Uani 1 1 d . . . . .
H6 H 0.2060 0.5273 0.4343 0.020 Uiso 1 1 calc R U . . .
C7 C 0.11298(18) 0.38837(16) 0.4092(3) 0.0169(5) Uani 1 1 d . . . . .
H7A H 0.0682 0.4351 0.3766 0.020 Uiso 1 1 calc R U . . .
H7AB H 0.0790 0.3455 0.4520 0.020 Uiso 1 1 calc R U . . .
C8 C 0.1414(2) 0.3539(2) 0.2750(3) 0.0324(8) Uani 1 1 d . . . . .
H8A H 0.0855 0.3276 0.2067 0.049 Uiso 1 1 calc R U . . .
H8AB H 0.1927 0.3132 0.3091 0.049 Uiso 1 1 calc R U . . .
H8AC H 0.1646 0.3986 0.2220 0.049 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 Cu1 2.7431(4) . ?
I1 Cu1 2.7431(4) 2_655 ?
I2 Cu1 2.6785(4) . ?
I2 Cu1 2.7650(4) 2_655 ?
Cu1 C1 1.907(2) . ?
Cu1 N1 1.907(2) . ?
Cu1 Cu1 2.4841(6) 2_655 ?
Cu1 I2 2.7650(4) 2_655 ?
N1 N1 1.162(4) 7_656 ?
C1 C1 1.162(4) 7_656 ?
N2 C2 1.349(3) . ?
N2 C6 1.351(3) . ?
N2 C7 1.487(3) . ?
C2 C3 1.372(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.371(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.505(4) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8AB 0.9800 . ?
C8 H8AC 0.9800 . ?

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
Cu1 I1 Cu1 53.846(13) . 2_655 ?
Cu1 I2 Cu1 54.274(12) . 2_655 ?
C1 Cu1 Cu1 176.04(7) . 2_655 ?
N1 Cu1 Cu1 176.04(7) . 2_655 ?
C1 Cu1 I2 119.27(7) . . ?
N1 Cu1 I2 119.27(7) . . ?
Cu1 Cu1 I2 64.639(13) 2_655 . ?
C1 Cu1 I1 115.42(7) . . ?
N1 Cu1 I1 115.42(7) . . ?
Cu1 Cu1 I1 63.078(7) 2_655 . ?
I2 Cu1 I1 102.319(11) . . ?
C1 Cu1 I2 116.41(7) . 2_655 ?
N1 Cu1 I2 116.41(7) . 2_655 ?
Cu1 Cu1 I2 61.088(12) 2_655 2_655 ?
I2 Cu1 I2 100.350(12) . 2_655 ?
I1 Cu1 I2 100.115(11) . 2_655 ?
N1 N1 Cu1 179.1(3) 7_656 . ?
C1 C1 Cu1 179.1(3) 7_656 . ?
C2 N2 C6 121.0(2) . . ?
C2 N2 C7 119.2(2) . . ?
C6 N2 C7 119.7(2) . . ?
N2 C2 C3 120.4(2) . . ?
N2 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 119.6(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 119.1(2) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 119.7(2) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
N2 C6 C5 120.2(2) . . ?
N2 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
N2 C7 C8 111.0(2) . . ?
N2 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
N2 C7 H7AB 109.4 . . ?
C8 C7 H7AB 109.4 . . ?
H7A C7 H7AB 108.0 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8AB 109.5 . . ?
H8A C8 H8AB 109.5 . . ?
C7 C8 H8AC 109.5 . . ?
H8A C8 H8AC 109.5 . . ?
H8AB C8 H8AC 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
C6 N2 C2 C3 -1.4(4) . . . . ?
C7 N2 C2 C3 176.7(2) . . . . ?
N2 C2 C3 C4 0.8(4) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 C6 -1.0(4) . . . . ?
C2 N2 C6 C5 0.7(4) . . . . ?
C7 N2 C6 C5 -177.4(2) . . . . ?
C4 C5 C6 N2 0.5(4) . . . . ?
C2 N2 C7 C8 -95.6(3) . . . . ?
C6 N2 C7 C8 82.5(3) . . . . ?

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
C2 H2 I2 0.95 3.20 4.091(3) 156.4 7_556
C3 H3 I2 0.95 3.16 3.913(3) 137.8 2_656
C6 H6 I1 0.95 3.25 4.057(3) 143.8 3_455
C7 H7A I1 0.99 3.04 3.974(3) 158.0 3_455
C7 H7AB I2 0.99 3.06 3.974(3) 153.3 7_556

_refine_diff_density_max         0.542
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.085

_shelxl_version_number           2014/5


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_P21onc_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1964375'
loop_
_audit_author_name
_audit_author_address
'Robert Pike'
;College of William and Mary
United States of America
;
_audit_update_record             
;
2019-11-07 deposited with the CCDC.	2019-12-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/5
_chemical_name_systematic        
'N-Methylpyridinium catena-mu2-cyanotri-mu2-iododicopper(I)'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '4(C6 H8 N), C2 Cu4 I6 N2'
_chemical_formula_sum            'C26 H32 Cu4 I6 N6'
_chemical_formula_weight         1444.13

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.6496(6)
_cell_length_b                   31.7022(12)
_cell_length_c                   8.2725(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.5140(10)
_cell_angle_gamma                90
_cell_volume                     3830.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9841
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      26.06

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.504
_exptl_crystal_F_000             2656
_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    7.053
_shelx_estimated_absorpt_T_min   0.333
_shelx_estimated_absorpt_T_max   0.602
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.3375
_exptl_absorpt_correction_T_max  0.5345
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_special_details           
; 
 ? 
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω and ψ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            58286
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.394
_diffrn_reflns_theta_max         26.079
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7585
_reflns_number_gt                6733
_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_cell_refinement       'SAINTPLUS (Bruker AXS, 2004)'
_computing_data_reduction        SAINTPLUS
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/5 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXLE (Hubschle, 2011)'
_computing_publication_material  'Mercury 3.7 (CCDC, 2016)'
_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)+(0.0139P)²+6.9053P] 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         7585
_refine_ls_number_parameters     385
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0226
_refine_ls_wR_factor_ref         0.0449
_refine_ls_wR_factor_gt          0.0435
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.149
_refine_ls_shift/su_max          0.002
_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
N1A N 0.4570(2) 0.37795(11) 0.7033(4) 0.0170(10) Uani 0.52(4) 1 d . . P A 1
C1A C 0.5352(2) 0.37514(11) 0.7091(4) 0.0171(10) Uani 0.52(4) 1 d . . P A 1
C2A C 0.9622(2) 0.35807(11) 0.8206(4) 0.0163(10) Uani 0.50(4) 1 d . . P B 1
N2A N 1.0407(2) 0.35885(11) 0.8116(4) 0.0141(9) Uani 0.50(4) 1 d . . P B 1
C1B C 0.4570(2) 0.37795(11) 0.7033(4) 0.0170(10) Uani 0.48(4) 1 d . . P A 2
N1B N 0.5352(2) 0.37514(11) 0.7091(4) 0.0171(10) Uani 0.48(4) 1 d . . P A 2
N2B N 0.9622(2) 0.35807(11) 0.8206(4) 0.0163(10) Uani 0.50(4) 1 d . . P B 2
C2B C 1.0407(2) 0.35885(11) 0.8116(4) 0.0141(9) Uani 0.50(4) 1 d . . P B 2
I1 I 0.74479(2) 0.41588(2) 0.99557(3) 0.01653(6) Uani 1 1 d . . . . .
I2 I 0.76905(2) 0.38937(2) 0.50296(3) 0.01649(6) Uani 1 1 d . . . . .
I3 I 0.73046(2) 0.29152(2) 0.84315(3) 0.02029(6) Uani 1 1 d . . . . .
I4 I 1.26210(2) 0.42222(2) 0.96525(3) 0.01677(6) Uani 1 1 d . . . . .
I5 I 1.20532(2) 0.39124(2) 0.47455(3) 0.01603(6) Uani 1 1 d . . . . .
I6 I 1.27456(2) 0.29420(2) 0.80062(3) 0.01690(6) Uani 1 1 d . . . . .
Cu1 Cu 0.66498(3) 0.36801(2) 0.74273(6) 0.01986(11) Uani 1 1 d . . . . .
Cu2 Cu 0.83169(3) 0.36066(2) 0.80728(6) 0.01917(11) Uani 1 1 d . . . . .
Cu3 Cu 1.16776(3) 0.36352(2) 0.77874(6) 0.01956(11) Uani 1 1 d . . . . .
Cu4 Cu 1.32838(3) 0.37555(2) 0.72276(6) 0.02055(11) Uani 1 1 d . . . . .
N3 N 0.4971(2) 0.29856(10) 0.4172(4) 0.0160(7) Uani 1 1 d . . . . .
C3 C 0.5752(3) 0.30954(13) 0.3520(5) 0.0214(9) Uani 1 1 d . . . . .
H3 H 0.6327 0.2999 0.3992 0.026 Uiso 1 1 calc R U . . .
C4 C 0.5708(3) 0.33484(14) 0.2163(5) 0.0291(10) Uani 1 1 d . . . . .
H4 H 0.6254 0.3427 0.1690 0.035 Uiso 1 1 calc R U . . .
C5 C 0.4874(3) 0.34877(14) 0.1496(5) 0.0302(11) Uani 1 1 d . . . . .
H5 H 0.4838 0.3655 0.0540 0.036 Uiso 1 1 calc R U . . .
C6 C 0.4088(3) 0.33831(14) 0.2219(5) 0.0284(10) Uani 1 1 d . . . . .
H6 H 0.3510 0.3486 0.1790 0.034 Uiso 1 1 calc R U . . .
C7 C 0.4149(3) 0.31315(13) 0.3551(5) 0.0217(9) Uani 1 1 d . . . . .
H7 H 0.3610 0.3057 0.4052 0.026 Uiso 1 1 calc R U . . .
C8 C 0.5019(3) 0.27023(13) 0.5603(5) 0.0245(9) Uani 1 1 d . . . . .
H8A H 0.4546 0.2484 0.5448 0.037 Uiso 1 1 calc R U . . .
H8B H 0.4920 0.2867 0.6577 0.037 Uiso 1 1 calc R U . . .
H8C H 0.5623 0.2569 0.5730 0.037 Uiso 1 1 calc R U . . .
N4 N 0.0532(2) 0.30037(10) 0.2530(4) 0.0165(7) Uani 1 1 d . . . . .
C9 C -0.0344(3) 0.30363(12) 0.1904(5) 0.0195(9) Uani 1 1 d . . . . .
H9 H -0.0471 0.3085 0.0775 0.023 Uiso 1 1 calc R U . . .
C10 C -0.1054(3) 0.29995(12) 0.2883(5) 0.0233(9) Uani 1 1 d . . . . .
H10 H -0.1670 0.3022 0.2440 0.028 Uiso 1 1 calc R U . . .
C11 C -0.0857(3) 0.29283(13) 0.4534(5) 0.0256(10) Uani 1 1 d . . . . .
H11 H -0.1340 0.2900 0.5228 0.031 Uiso 1 1 calc R U . . .
C12 C 0.0038(3) 0.28997(12) 0.5153(5) 0.0232(9) Uani 1 1 d . . . . .
H12 H 0.0178 0.2854 0.6280 0.028 Uiso 1 1 calc R U . . .
C13 C 0.0734(3) 0.29376(12) 0.4125(5) 0.0199(9) Uani 1 1 d . . . . .
H13 H 0.1355 0.2917 0.4545 0.024 Uiso 1 1 calc R U . . .
C14 C 0.1289(3) 0.30524(13) 0.1459(5) 0.0230(9) Uani 1 1 d . . . . .
H14A H 0.1736 0.2825 0.1678 0.035 Uiso 1 1 calc R U . . .
H14B H 0.1589 0.3326 0.1668 0.035 Uiso 1 1 calc R U . . .
H14C H 0.1044 0.3039 0.0324 0.035 Uiso 1 1 calc R U . . .
N5 N -0.0066(2) 0.45580(11) 0.2215(4) 0.0222(8) Uani 1 1 d . . . . .
C15 C -0.0814(3) 0.47054(13) 0.2882(5) 0.0190(9) Uani 1 1 d . . . . .
H15 H -0.1301 0.4519 0.3071 0.023 Uiso 1 1 calc R U . . .
C16 C -0.0875(3) 0.51207(14) 0.3285(5) 0.0255(10) Uani 1 1 d . . . . .
H16 H -0.1410 0.5223 0.3731 0.031 Uiso 1 1 calc R U . . .
C17 C -0.0165(3) 0.53912(14) 0.3048(6) 0.0324(11) Uani 1 1 d . . . . .
H17 H -0.0197 0.5679 0.3359 0.039 Uiso 1 1 calc R U . . .
C18 C 0.0592(3) 0.52401(16) 0.2355(6) 0.0361(12) Uani 1 1 d . . . . .
H18 H 0.1085 0.5424 0.2168 0.043 Uiso 1 1 calc R U . . .
C19 C 0.0633(3) 0.48234(17) 0.1934(6) 0.0349(12) Uani 1 1 d . . . . .
H19 H 0.1152 0.4719 0.1443 0.042 Uiso 1 1 calc R U . . .
C20 C -0.0017(4) 0.41098(16) 0.1806(7) 0.0491(16) Uani 1 1 d . . . . .
H20A H 0.0535 0.4057 0.1240 0.074 Uiso 1 1 calc R U . . .
H20B H -0.0559 0.4031 0.1102 0.074 Uiso 1 1 calc R U . . .
H20C H 0.0007 0.3941 0.2802 0.074 Uiso 1 1 calc R U . . .
N6 N 0.4046(2) 0.48830(10) 0.3139(4) 0.0160(7) Uani 1 1 d . . . . .
C21 C 0.4423(3) 0.45238(12) 0.3760(5) 0.0211(9) Uani 1 1 d . . . . .
H21 H 0.4063 0.4331 0.4315 0.025 Uiso 1 1 calc R U . . .
C22 C 0.5333(3) 0.44385(14) 0.3586(5) 0.0254(10) Uani 1 1 d . . . . .
H22 H 0.5606 0.4189 0.4039 0.030 Uiso 1 1 calc R U . . .
C23 C 0.5844(3) 0.47173(15) 0.2749(5) 0.0268(10) Uani 1 1 d . . . . .
H23 H 0.6470 0.4661 0.2612 0.032 Uiso 1 1 calc R U . . .
C24 C 0.5435(3) 0.50802(15) 0.2113(5) 0.0279(10) Uani 1 1 d . . . . .
H24 H 0.5778 0.5275 0.1534 0.033 Uiso 1 1 calc R U . . .
C25 C 0.4533(3) 0.51566(13) 0.2323(5) 0.0221(9) Uani 1 1 d . . . . .
H25 H 0.4250 0.5406 0.1886 0.026 Uiso 1 1 calc R U . . .
C26 C 0.3075(3) 0.49782(13) 0.3363(5) 0.0234(9) Uani 1 1 d . . . . .
H26A H 0.3037 0.5242 0.3974 0.035 Uiso 1 1 calc R U . . .
H26B H 0.2811 0.4748 0.3963 0.035 Uiso 1 1 calc R U . . .
H26C H 0.2735 0.5008 0.2301 0.035 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1A C1A 1.146(5) . ?
N1A Cu4 1.905(4) 1_455 ?
C1A Cu1 1.913(4) . ?
C2A N2A 1.158(5) . ?
C2A Cu2 1.909(4) . ?
N2A Cu3 1.908(3) . ?
C1B N1B 1.146(5) . ?
C1B Cu4 1.905(4) 1_455 ?
N1B Cu1 1.913(4) . ?
N2B C2B 1.158(5) . ?
N2B Cu2 1.909(4) . ?
C2B Cu3 1.908(3) . ?
I1 Cu2 2.7247(6) . ?
I1 Cu1 2.7676(6) . ?
I2 Cu1 2.6820(6) . ?
I2 Cu2 2.7650(6) . ?
I3 Cu2 2.6758(6) . ?
I3 Cu1 2.7139(6) . ?
I4 Cu3 2.7235(6) . ?
I4 Cu4 2.7318(6) . ?
I5 Cu4 2.6704(6) . ?
I5 Cu3 2.7613(6) . ?
I6 Cu3 2.6954(6) . ?
I6 Cu4 2.7869(6) . ?
Cu1 Cu2 2.4696(6) . ?
Cu3 Cu4 2.4634(6) . ?
Cu4 C1B 1.905(4) 1_655 ?
Cu4 N1A 1.905(4) 1_655 ?
N3 C3 1.349(5) . ?
N3 C7 1.353(5) . ?
N3 C8 1.483(5) . ?
C3 C4 1.377(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.357(6) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
N4 C13 1.346(5) . ?
N4 C9 1.350(5) . ?
N4 C14 1.481(5) . ?
C9 C10 1.372(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.373(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(6) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
N5 C15 1.348(5) . ?
N5 C19 1.359(6) . ?
N5 C20 1.464(6) . ?
C15 C16 1.363(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.373(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.375(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.369(7) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N6 C25 1.339(5) . ?
N6 C21 1.349(5) . ?
N6 C26 1.480(5) . ?
C21 C22 1.378(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.380(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.367(6) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

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
C1A N1A Cu4 170.1(3) . 1_455 ?
N1A C1A Cu1 173.6(3) . . ?
N2A C2A Cu2 172.1(3) . . ?
C2A N2A Cu3 174.5(3) . . ?
N1B C1B Cu4 170.1(3) . 1_455 ?
C1B N1B Cu1 173.6(3) . . ?
C2B N2B Cu2 172.1(3) . . ?
N2B C2B Cu3 174.5(3) . . ?
Cu2 I1 Cu1 53.435(14) . . ?
Cu1 I2 Cu2 53.896(14) . . ?
Cu2 I3 Cu1 54.536(15) . . ?
Cu3 I4 Cu4 53.687(15) . . ?
Cu4 I5 Cu3 53.907(15) . . ?
Cu3 I6 Cu4 53.370(15) . . ?
N1B Cu1 Cu2 175.69(11) . . ?
C1A Cu1 Cu2 175.69(11) . . ?
N1B Cu1 I2 118.62(11) . . ?
C1A Cu1 I2 118.62(11) . . ?
Cu2 Cu1 I2 64.767(17) . . ?
N1B Cu1 I3 118.25(11) . . ?
C1A Cu1 I3 118.25(11) . . ?
Cu2 Cu1 I3 61.945(17) . . ?
I2 Cu1 I3 104.130(18) . . ?
N1B Cu1 I1 113.64(11) . . ?
C1A Cu1 I1 113.64(11) . . ?
Cu2 Cu1 I1 62.393(17) . . ?
I2 Cu1 I1 100.928(17) . . ?
I3 Cu1 I1 98.074(17) . . ?
N2B Cu2 Cu1 170.35(11) . . ?
C2A Cu2 Cu1 170.35(11) . . ?
N2B Cu2 I3 121.33(11) . . ?
C2A Cu2 I3 121.33(11) . . ?
Cu1 Cu2 I3 63.518(17) . . ?
N2B Cu2 I1 120.38(11) . . ?
C2A Cu2 I1 120.38(11) . . ?
Cu1 Cu2 I1 64.172(17) . . ?
I3 Cu2 I1 100.076(17) . . ?
N2B Cu2 I2 109.02(11) . . ?
C2A Cu2 I2 109.02(11) . . ?
Cu1 Cu2 I2 61.337(17) . . ?
I3 Cu2 I2 102.917(18) . . ?
I1 Cu2 I2 99.931(17) . . ?
C2B Cu3 Cu4 174.78(10) . . ?
N2A Cu3 Cu4 174.78(10) . . ?
C2B Cu3 I6 119.65(10) . . ?
N2A Cu3 I6 119.65(10) . . ?
Cu4 Cu3 I6 65.216(17) . . ?
C2B Cu3 I4 115.44(11) . . ?
N2A Cu3 I4 115.44(11) . . ?
Cu4 Cu3 I4 63.329(17) . . ?
I6 Cu3 I4 104.656(18) . . ?
C2B Cu3 I5 114.91(10) . . ?
N2A Cu3 I5 114.91(10) . . ?
Cu4 Cu3 I5 61.162(17) . . ?
I6 Cu3 I5 99.460(17) . . ?
I4 Cu3 I5 99.805(17) . . ?
C1B Cu4 Cu3 171.03(11) 1_655 . ?
N1A Cu4 Cu3 171.03(11) 1_655 . ?
C1B Cu4 I5 122.68(11) 1_655 . ?
N1A Cu4 I5 122.68(11) 1_655 . ?
Cu3 Cu4 I5 64.931(17) . . ?
C1B Cu4 I4 116.84(11) 1_655 . ?
N1A Cu4 I4 116.84(11) 1_655 . ?
Cu3 Cu4 I4 62.984(17) . . ?
I5 Cu4 I4 101.904(18) . . ?
C1B Cu4 I6 110.86(11) 1_655 . ?
N1A Cu4 I6 110.86(11) 1_655 . ?
Cu3 Cu4 I6 61.414(17) . . ?
I5 Cu4 I6 99.431(17) . . ?
I4 Cu4 I6 102.008(18) . . ?
C3 N3 C7 121.2(4) . . ?
C3 N3 C8 119.1(3) . . ?
C7 N3 C8 119.7(3) . . ?
N3 C3 C4 119.3(4) . . ?
N3 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 119.8(4) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 119.7(4) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 119.3(4) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
N3 C7 C6 120.6(4) . . ?
N3 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C13 N4 C9 121.1(3) . . ?
C13 N4 C14 119.1(3) . . ?
C9 N4 C14 119.8(3) . . ?
N4 C9 C10 120.6(4) . . ?
N4 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C11 119.0(4) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C12 C11 C10 119.6(4) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 119.6(4) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
N4 C13 C12 120.0(4) . . ?
N4 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C15 N5 C19 120.2(4) . . ?
C15 N5 C20 119.2(4) . . ?
C19 N5 C20 120.6(4) . . ?
N5 C15 C16 120.4(4) . . ?
N5 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C17 120.2(4) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C18 119.1(4) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C19 C18 C17 119.6(4) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
N5 C19 C18 120.4(4) . . ?
N5 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
N5 C20 H20A 109.5 . . ?
N5 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N5 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C25 N6 C21 121.4(3) . . ?
C25 N6 C26 119.1(3) . . ?
C21 N6 C26 119.5(3) . . ?
N6 C21 C22 119.7(4) . . ?
N6 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C21 C22 C23 119.6(4) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C22 C23 C24 119.2(4) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C25 C24 C23 119.6(4) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
N6 C25 C24 120.5(4) . . ?
N6 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
N6 C26 H26A 109.5 . . ?
N6 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N6 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
C7 N3 C3 C4 -2.4(6) . . . . ?
C8 N3 C3 C4 178.2(4) . . . . ?
N3 C3 C4 C5 0.4(6) . . . . ?
C3 C4 C5 C6 1.9(6) . . . . ?
C4 C5 C6 C7 -2.2(7) . . . . ?
C3 N3 C7 C6 2.0(6) . . . . ?
C8 N3 C7 C6 -178.5(4) . . . . ?
C5 C6 C7 N3 0.3(6) . . . . ?
C13 N4 C9 C10 -0.5(6) . . . . ?
C14 N4 C9 C10 -178.8(4) . . . . ?
N4 C9 C10 C11 0.0(6) . . . . ?
C9 C10 C11 C12 0.5(6) . . . . ?
C10 C11 C12 C13 -0.7(6) . . . . ?
C9 N4 C13 C12 0.3(6) . . . . ?
C14 N4 C13 C12 178.7(4) . . . . ?
C11 C12 C13 N4 0.2(6) . . . . ?
C19 N5 C15 C16 -0.3(6) . . . . ?
C20 N5 C15 C16 179.5(4) . . . . ?
N5 C15 C16 C17 -1.4(6) . . . . ?
C15 C16 C17 C18 2.0(7) . . . . ?
C16 C17 C18 C19 -0.9(7) . . . . ?
C15 N5 C19 C18 1.4(6) . . . . ?
C20 N5 C19 C18 -178.4(4) . . . . ?
C17 C18 C19 N5 -0.8(7) . . . . ?
C25 N6 C21 C22 1.4(6) . . . . ?
C26 N6 C21 C22 -178.5(4) . . . . ?
N6 C21 C22 C23 -1.3(6) . . . . ?
C21 C22 C23 C24 0.6(6) . . . . ?
C22 C23 C24 C25 0.0(6) . . . . ?
C21 N6 C25 C24 -0.8(6) . . . . ?
C26 N6 C25 C24 179.1(4) . . . . ?
C23 C24 C25 N6 0.1(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
C3 H3 I3 0.95 3.28 3.933(4) 127.4 4_565
C4 H4 I1 0.95 3.30 4.142(4) 148.6 1_554
C6 H6 I4 0.95 3.15 3.935(4) 141.4 1_454
C9 H9 N2B 0.95 2.66 3.509(5) 149.8 1_454
C14 H14A I6 0.98 3.01 3.962(4) 164.4 4_465
C14 H14B I5 0.98 3.18 3.949(4) 136.2 1_455
C14 H14C N2A 0.98 2.64 3.413(5) 135.8 1_454
C15 H15 I1 0.95 3.25 3.792(4) 118.2 1_454
C15 H15 I2 0.95 3.02 3.898(4) 154.6 1_455
C16 H16 I5 0.95 3.19 3.934(4) 136.6 3_666
C18 H18 I1 0.95 3.17 4.048(5) 154.6 3_666
C19 H19 I4 0.95 3.13 4.068(5) 168.8 1_454
C20 H20B I1 0.98 3.03 3.908(5) 150.4 1_454
C20 H20C I5 0.98 3.29 3.787(5) 113.4 1_455
C21 H21 I5 0.95 3.27 4.113(4) 148.4 1_455
C22 H22 I2 0.95 3.24 3.961(4) 134.4 .
C24 H24 I4 0.95 3.06 3.974(4) 161.8 3_766
C25 H25 I1 0.95 3.13 3.978(4) 149.0 3_666
C26 H26A I2 0.98 3.08 4.006(4) 158.8 3_666
C26 H26B I5 0.98 2.96 3.903(4) 161.3 1_455
C26 H26C I1 0.98 3.23 3.909(4) 127.6 3_666
C26 H26C I4 0.98 3.31 3.910(4) 121.0 1_454

_refine_diff_density_max         0.739
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.118

_shelxl_version_number           2014/5


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
_exptl_crystal_preparation       Luminescent
