# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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#  from this site to visualise CIF-encoded structures and 
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data_tgn355

_database_code_depnum_ccdc_archive 'CCDC 1021437'
_audit_contact_author            'Joerg Sundermeyer'
_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
'Chloro tris(2-pyridyl)phosphineoxide copper(I)'
_chemical_name_common            'C1; CuCltpypo'
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 Cl Cu N3 O P, 0.5(C2 H3 N)'
_chemical_formula_sum            'C16 H13.50 Cl Cu N3.50 O P'
_chemical_formula_weight         400.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   8.4558(6)
_cell_length_b                   27.6843(13)
_cell_length_c                   28.3435(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6635.0(7)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7307
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      27.11

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_F_000             3248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.660
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    1.582
_shelx_estimated_absorpt_T_min   0.422
_shelx_estimated_absorpt_T_max   0.753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.414
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   
;
Bruker: SADABS v2012/1, Bruker AXS Inc., 
Madison, Wisconsin, USA, 2012.
;

_exptl_special_details           
; 
Department of Chemistry 
University of Anywhere 
Sometown 
Somewhere, UK 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS Microfocus Source'
_diffrn_measurement_device_type  'D8 Quest (Bruker AXS Inc.)'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            25305
_diffrn_reflns_av_unetI/netI     0.0829
_diffrn_reflns_av_R_equivalents  0.0891
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.610
_diffrn_reflns_theta_max         27.109
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7307
_reflns_number_gt                5432
_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       
;
Bruker: Bruker Instrument Service v3.0.26, Bruker AXS Inc., 
Madison, Wisconsin, USA, 2012.
;
_computing_cell_refinement       
;
Bruker: APEX2 v2013.10-0, Bruker AXS Inc., 
Madison, Wisconsin, USA, 2012.
;
_computing_data_reduction        
;
Bruker: SAINT V8.27B, Bruker AXS Inc., 
Madison, Wisconsin, USA, 2012.
;
_computing_structure_solution    
;
SIR97 (A. Altomare, M. C. Burla, M. Camalli, G. Cascarano, C. Giacovazzo, 
A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, 
J. Appl. Crystallogr. 1999, 32, 115-119.)
;
_computing_structure_refinement  
;
SHELXL-2014 (G. Sheldrick, Acta Cryst. A 2008, 64, 112-122)
;
_computing_molecular_graphics    
;
K. Brandenburg, H. Putz: 
Diamond - Crystal and Molecular Structure Visualization v3.2i, 
Crystal Impact GbR, Bonn, Germany, 2012
;
_computing_publication_material  
;
WinGX publication routines (L. Farrugia, 
J. Appl. Crystallogr. 1999, 32, 837-838.)
;
_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)+(0.1012P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7307
_refine_ls_number_parameters     425
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0658
_refine_ls_wR_factor_ref         0.1677
_refine_ls_wR_factor_gt          0.1534
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
Cu2 Cu 0.68957(6) 0.02614(2) 0.61155(2) 0.01271(16) Uani 1 1 d . . . . .
Cu1 Cu 0.57489(6) 0.28279(2) 0.63830(2) 0.01158(15) Uani 1 1 d . . . . .
Cl1 Cl 0.47002(13) 0.28457(4) 0.70977(4) 0.0206(3) Uani 1 1 d . . . . .
P2 P 0.51635(13) 0.03752(4) 0.70693(4) 0.0104(2) Uani 1 1 d . . . . .
Cl2 Cl 0.77449(13) 0.01641(4) 0.53800(4) 0.0186(2) Uani 1 1 d . . . . .
P1 P 0.74697(13) 0.26092(4) 0.54373(4) 0.0097(2) Uani 1 1 d . . . . .
O1 O 0.8278(3) 0.25103(11) 0.49808(10) 0.0155(7) Uani 1 1 d . . . . .
O2 O 0.4353(3) 0.04368(11) 0.75297(10) 0.0167(7) Uani 1 1 d . . . . .
N6 N 0.7252(4) -0.02342(12) 0.66463(12) 0.0124(7) Uani 1 1 d . . . . .
N1 N 0.5370(4) 0.21861(12) 0.60279(12) 0.0118(7) Uani 1 1 d . . . . .
N4 N 0.4450(4) 0.02423(12) 0.61453(12) 0.0105(7) Uani 1 1 d . . . . .
C5 C 0.4400(5) 0.18355(16) 0.61715(15) 0.0150(9) Uani 1 1 d . . . . .
H5 H 0.3790 0.1885 0.6449 0.018 Uiso 1 1 calc R U . . .
C6 C 0.8831(5) 0.27216(14) 0.59221(14) 0.0090(8) Uani 1 1 d . . . . .
N2 N 0.8166(4) 0.28265(12) 0.63438(12) 0.0107(7) Uani 1 1 d . . . . .
C29 C 0.8145(5) -0.09828(16) 0.69721(17) 0.0202(10) Uani 1 1 d . . . . .
H29 H 0.8762 -0.1268 0.6940 0.024 Uiso 1 1 calc R U . . .
N5 N 0.7280(4) 0.08640(12) 0.65236(12) 0.0128(7) Uani 1 1 d . . . . .
C26 C 0.6390(5) -0.01642(14) 0.70397(14) 0.0107(8) Uani 1 1 d . . . . .
C19 C 0.1821(5) 0.01983(14) 0.58275(15) 0.0140(9) Uani 1 1 d . . . . .
H19 H 0.1158 0.0150 0.5561 0.017 Uiso 1 1 calc R U . . .
C2 C 0.6170(5) 0.16876(15) 0.53807(15) 0.0144(9) Uani 1 1 d . . . . .
H2 H 0.6807 0.1647 0.5108 0.017 Uiso 1 1 calc R U . . .
C3 C 0.5176(5) 0.13186(15) 0.55356(16) 0.0168(9) Uani 1 1 d . . . . .
H3 H 0.5134 0.1018 0.5374 0.020 Uiso 1 1 calc R U . . .
C20 C 0.3459(5) 0.01809(14) 0.57815(15) 0.0119(8) Uani 1 1 d . . . . .
H20 H 0.3894 0.0123 0.5478 0.014 Uiso 1 1 calc R U . . .
C17 C 0.2173(5) 0.03467(14) 0.66521(15) 0.0139(9) Uani 1 1 d . . . . .
H17 H 0.1756 0.0405 0.6958 0.017 Uiso 1 1 calc R U . . .
C9 C 1.0773(5) 0.28810(15) 0.66711(16) 0.0165(9) Uani 1 1 d . . . . .
H14 H 1.1421 0.2938 0.6939 0.020 Uiso 1 1 calc R U . . .
N3 N 0.5391(4) 0.32611(12) 0.58076(12) 0.0125(7) Uani 1 1 d . . . . .
C8 C 1.1450(5) 0.27710(15) 0.62381(16) 0.0156(9) Uani 1 1 d . . . . .
H13 H 1.2567 0.2754 0.6204 0.019 Uiso 1 1 calc R U . . .
C1 C 0.6207(5) 0.21123(14) 0.56330(14) 0.0099(8) Uani 1 1 d . . . . .
C11 C 0.6207(5) 0.31445(14) 0.54168(14) 0.0095(8) Uani 1 1 d . . . . .
C12 C 0.6135(5) 0.34118(15) 0.50039(15) 0.0154(9) Uani 1 1 d . . . . .
H7 H 0.6711 0.3315 0.4732 0.018 Uiso 1 1 calc R U . . .
C14 C 0.4338(6) 0.39461(15) 0.53947(17) 0.0197(10) Uani 1 1 d . . . . .
H9 H 0.3669 0.4222 0.5396 0.024 Uiso 1 1 calc R U . . .
C30 C 0.8126(5) -0.06411(16) 0.66187(16) 0.0174(9) Uani 1 1 d . . . . .
H30 H 0.8752 -0.0694 0.6345 0.021 Uiso 1 1 calc R U . . .
C4 C 0.4246(5) 0.14020(16) 0.59326(16) 0.0171(9) Uani 1 1 d . . . . .
H4 H 0.3516 0.1165 0.6038 0.021 Uiso 1 1 calc R U . . .
C22 C 0.6491(6) 0.12778(16) 0.72306(16) 0.0184(9) Uani 1 1 d . . . . .
H22 H 0.5876 0.1280 0.7511 0.022 Uiso 1 1 calc R U . . .
C27 C 0.6376(5) -0.04899(15) 0.74113(15) 0.0151(9) Uani 1 1 d . . . . .
H27 H 0.5769 -0.0425 0.7686 0.018 Uiso 1 1 calc R U . . .
C21 C 0.6433(5) 0.08897(14) 0.69258(14) 0.0115(8) Uani 1 1 d . . . . .
N7 N 0.3572(6) -0.08880(16) 0.64601(16) 0.0311(10) Uani 1 1 d . . . . .
C10 C 0.9140(5) 0.29076(14) 0.67083(15) 0.0133(9) Uani 1 1 d . . . . .
H15 H 0.8692 0.2987 0.7006 0.016 Uiso 1 1 calc R U . . .
C7 C 1.0451(5) 0.26851(14) 0.58523(15) 0.0134(9) Uani 1 1 d . . . . .
H12 H 1.0871 0.2604 0.5552 0.016 Uiso 1 1 calc R U . . .
C24 C 0.8382(6) 0.16359(15) 0.67142(17) 0.0212(10) Uani 1 1 d . . . . .
H24 H 0.9096 0.1888 0.6636 0.025 Uiso 1 1 calc R U . . .
C16 C 0.3805(5) 0.03187(13) 0.65768(14) 0.0092(8) Uani 1 1 d . . . . .
C25 C 0.8238(5) 0.12342(16) 0.64258(16) 0.0178(9) Uani 1 1 d . . . . .
H25 H 0.8851 0.1221 0.6145 0.021 Uiso 1 1 calc R U . . .
C15 C 0.4481(5) 0.36516(15) 0.57926(16) 0.0159(9) Uani 1 1 d . . . . .
H10 H 0.3897 0.3735 0.6067 0.019 Uiso 1 1 calc R U . . .
C13 C 0.5212(6) 0.38205(16) 0.49959(16) 0.0218(10) Uani 1 1 d . . . . .
H8 H 0.5170 0.4016 0.4721 0.026 Uiso 1 1 calc R U . . .
C28 C 0.7246(6) -0.09059(16) 0.73780(16) 0.0207(10) Uani 1 1 d . . . . .
H28 H 0.7238 -0.1137 0.7626 0.025 Uiso 1 1 calc R U . . .
C23 C 0.7464(6) 0.16628(16) 0.71192(17) 0.0236(11) Uani 1 1 d . . . . .
H23 H 0.7503 0.1940 0.7316 0.028 Uiso 1 1 calc R U . . .
C31 C 0.5516(7) -0.0977(2) 0.5757(2) 0.0422(15) Uani 1 1 d . . . . .
H31A H 0.6349 -0.1209 0.5838 0.063 Uiso 1 1 calc R U . . .
H31B H 0.5993 -0.0663 0.5685 0.063 Uiso 1 1 calc R U . . .
H31C H 0.4934 -0.1094 0.5480 0.063 Uiso 1 1 calc R U . . .
C18 C 0.1178(5) 0.02865(15) 0.62647(16) 0.0156(9) Uani 1 1 d . . . . .
H18 H 0.0064 0.0306 0.6302 0.019 Uiso 1 1 calc R U . . .
C32 C 0.4421(6) -0.09254(17) 0.61579(18) 0.0238(11) 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
Cu2 N5 2.056(4) . ?
Cu2 N6 2.058(4) . ?
Cu2 N4 2.070(4) . ?
Cu2 Cl2 2.2213(11) . ?
Cu1 N2 2.047(4) . ?
Cu1 N3 2.047(3) . ?
Cu1 N1 2.067(3) . ?
Cu1 Cl1 2.2120(11) . ?
P2 O2 1.484(3) . ?
P2 C16 1.814(4) . ?
P2 C26 1.820(4) . ?
P2 C21 1.829(4) . ?
P1 O1 1.489(3) . ?
P1 C6 1.820(4) . ?
P1 C11 1.827(4) . ?
P1 C1 1.828(4) . ?
N6 C26 1.346(5) . ?
N6 C30 1.349(5) . ?
N1 C5 1.334(5) . ?
N1 C1 1.340(5) . ?
N4 C20 1.340(5) . ?
N4 C16 1.356(5) . ?
C5 C4 1.384(6) . ?
C5 H5 0.9500 . ?
C6 N2 1.353(5) . ?
C6 C7 1.388(6) . ?
N2 C10 1.341(5) . ?
C29 C30 1.378(6) . ?
C29 C28 1.395(7) . ?
C29 H29 0.9500 . ?
N5 C25 1.336(6) . ?
N5 C21 1.348(5) . ?
C26 C27 1.387(6) . ?
C19 C18 1.375(6) . ?
C19 C20 1.392(6) . ?
C19 H19 0.9500 . ?
C2 C1 1.377(6) . ?
C2 C3 1.394(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(6) . ?
C3 H3 0.9500 . ?
C20 H20 0.9500 . ?
C17 C18 1.393(6) . ?
C17 C16 1.398(6) . ?
C17 H17 0.9500 . ?
C9 C10 1.386(6) . ?
C9 C8 1.388(6) . ?
C9 H14 0.9500 . ?
N3 C15 1.327(5) . ?
N3 C11 1.345(5) . ?
C8 C7 1.402(6) . ?
C8 H13 0.9500 . ?
C11 C12 1.386(6) . ?
C12 C13 1.375(6) . ?
C12 H7 0.9500 . ?
C14 C13 1.394(7) . ?
C14 C15 1.397(6) . ?
C14 H9 0.9500 . ?
C30 H30 0.9500 . ?
C4 H4 0.9500 . ?
C22 C21 1.380(6) . ?
C22 C23 1.383(7) . ?
C22 H22 0.9500 . ?
C27 C28 1.370(6) . ?
C27 H27 0.9500 . ?
N7 C32 1.122(7) . ?
C10 H15 0.9500 . ?
C7 H12 0.9500 . ?
C24 C25 1.386(6) . ?
C24 C23 1.388(7) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C15 H10 0.9500 . ?
C13 H8 0.9500 . ?
C28 H28 0.9500 . ?
C23 H23 0.9500 . ?
C31 C32 1.473(7) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 Cu2 N6 96.12(14) . . ?
N5 Cu2 N4 98.94(13) . . ?
N6 Cu2 N4 95.71(14) . . ?
N5 Cu2 Cl2 125.12(11) . . ?
N6 Cu2 Cl2 123.91(10) . . ?
N4 Cu2 Cl2 110.98(10) . . ?
N2 Cu1 N3 96.05(14) . . ?
N2 Cu1 N1 97.29(13) . . ?
N3 Cu1 N1 95.33(13) . . ?
N2 Cu1 Cl1 116.75(10) . . ?
N3 Cu1 Cl1 131.10(10) . . ?
N1 Cu1 Cl1 113.76(10) . . ?
O2 P2 C16 113.22(19) . . ?
O2 P2 C26 113.46(19) . . ?
C16 P2 C26 104.75(18) . . ?
O2 P2 C21 112.14(19) . . ?
C16 P2 C21 105.52(18) . . ?
C26 P2 C21 107.10(19) . . ?
O1 P1 C6 113.41(19) . . ?
O1 P1 C11 112.92(18) . . ?
C6 P1 C11 104.78(18) . . ?
O1 P1 C1 113.19(18) . . ?
C6 P1 C1 105.63(18) . . ?
C11 P1 C1 106.18(19) . . ?
C26 N6 C30 117.7(4) . . ?
C26 N6 Cu2 115.5(3) . . ?
C30 N6 Cu2 126.5(3) . . ?
C5 N1 C1 117.9(4) . . ?
C5 N1 Cu1 124.9(3) . . ?
C1 N1 Cu1 117.1(3) . . ?
C20 N4 C16 117.5(4) . . ?
C20 N4 Cu2 126.7(3) . . ?
C16 N4 Cu2 115.8(3) . . ?
N1 C5 C4 122.6(4) . . ?
N1 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
N2 C6 C7 123.5(4) . . ?
N2 C6 P1 116.1(3) . . ?
C7 C6 P1 120.3(3) . . ?
C10 N2 C6 117.5(4) . . ?
C10 N2 Cu1 124.9(3) . . ?
C6 N2 Cu1 117.6(3) . . ?
C30 C29 C28 119.2(4) . . ?
C30 C29 H29 120.4 . . ?
C28 C29 H29 120.4 . . ?
C25 N5 C21 117.2(4) . . ?
C25 N5 Cu2 127.0(3) . . ?
C21 N5 Cu2 115.8(3) . . ?
N6 C26 C27 122.7(4) . . ?
N6 C26 P2 117.7(3) . . ?
C27 C26 P2 119.6(3) . . ?
C18 C19 C20 118.9(4) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C1 C2 C3 118.4(4) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 118.3(4) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
N4 C20 C19 123.1(4) . . ?
N4 C20 H20 118.4 . . ?
C19 C20 H20 118.4 . . ?
C18 C17 C16 118.0(4) . . ?
C18 C17 H17 121.0 . . ?
C16 C17 H17 121.0 . . ?
C10 C9 C8 119.3(4) . . ?
C10 C9 H14 120.3 . . ?
C8 C9 H14 120.3 . . ?
C15 N3 C11 117.8(4) . . ?
C15 N3 Cu1 126.0(3) . . ?
C11 N3 Cu1 116.1(3) . . ?
C9 C8 C7 118.6(4) . . ?
C9 C8 H13 120.7 . . ?
C7 C8 H13 120.7 . . ?
N1 C1 C2 123.5(4) . . ?
N1 C1 P1 116.6(3) . . ?
C2 C1 P1 119.9(3) . . ?
N3 C11 C12 123.0(4) . . ?
N3 C11 P1 117.9(3) . . ?
C12 C11 P1 119.1(3) . . ?
C13 C12 C11 118.6(4) . . ?
C13 C12 H7 120.7 . . ?
C11 C12 H7 120.7 . . ?
C13 C14 C15 117.6(4) . . ?
C13 C14 H9 121.2 . . ?
C15 C14 H9 121.2 . . ?
N6 C30 C29 122.5(4) . . ?
N6 C30 H30 118.7 . . ?
C29 C30 H30 118.7 . . ?
C5 C4 C3 119.1(4) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C21 C22 C23 118.6(4) . . ?
C21 C22 H22 120.7 . . ?
C23 C22 H22 120.7 . . ?
C28 C27 C26 119.3(4) . . ?
C28 C27 H27 120.3 . . ?
C26 C27 H27 120.3 . . ?
N5 C21 C22 123.5(4) . . ?
N5 C21 P2 117.3(3) . . ?
C22 C21 P2 119.2(3) . . ?
N2 C10 C9 123.0(4) . . ?
N2 C10 H15 118.5 . . ?
C9 C10 H15 118.5 . . ?
C6 C7 C8 118.1(4) . . ?
C6 C7 H12 120.9 . . ?
C8 C7 H12 120.9 . . ?
C25 C24 C23 118.8(4) . . ?
C25 C24 H24 120.6 . . ?
C23 C24 H24 120.6 . . ?
N4 C16 C17 122.9(4) . . ?
N4 C16 P2 116.9(3) . . ?
C17 C16 P2 120.2(3) . . ?
N5 C25 C24 123.1(4) . . ?
N5 C25 H25 118.4 . . ?
C24 C25 H25 118.4 . . ?
N3 C15 C14 123.5(4) . . ?
N3 C15 H10 118.3 . . ?
C14 C15 H10 118.3 . . ?
C12 C13 C14 119.5(4) . . ?
C12 C13 H8 120.2 . . ?
C14 C13 H8 120.2 . . ?
C27 C28 C29 118.5(4) . . ?
C27 C28 H28 120.7 . . ?
C29 C28 H28 120.7 . . ?
C22 C23 C24 118.7(4) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
C32 C31 H31A 109.5 . . ?
C32 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C32 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C19 C18 C17 119.5(4) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
N7 C32 C31 179.1(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
C1 N1 C5 C4 0.8(6) . . . . ?
Cu1 N1 C5 C4 -176.7(3) . . . . ?
O1 P1 C6 N2 178.3(3) . . . . ?
C11 P1 C6 N2 54.7(3) . . . . ?
C1 P1 C6 N2 -57.2(3) . . . . ?
O1 P1 C6 C7 -3.4(4) . . . . ?
C11 P1 C6 C7 -127.0(3) . . . . ?
C1 P1 C6 C7 121.1(3) . . . . ?
C7 C6 N2 C10 1.3(6) . . . . ?
P1 C6 N2 C10 179.5(3) . . . . ?
C7 C6 N2 Cu1 -176.7(3) . . . . ?
P1 C6 N2 Cu1 1.5(4) . . . . ?
C30 N6 C26 C27 0.2(6) . . . . ?
Cu2 N6 C26 C27 173.7(3) . . . . ?
C30 N6 C26 P2 -178.1(3) . . . . ?
Cu2 N6 C26 P2 -4.7(4) . . . . ?
O2 P2 C26 N6 -175.8(3) . . . . ?
C16 P2 C26 N6 60.2(4) . . . . ?
C21 P2 C26 N6 -51.5(4) . . . . ?
O2 P2 C26 C27 5.8(4) . . . . ?
C16 P2 C26 C27 -118.2(3) . . . . ?
C21 P2 C26 C27 130.1(3) . . . . ?
C1 C2 C3 C4 1.3(6) . . . . ?
C16 N4 C20 C19 0.8(6) . . . . ?
Cu2 N4 C20 C19 -176.4(3) . . . . ?
C18 C19 C20 N4 0.6(6) . . . . ?
C10 C9 C8 C7 -0.7(6) . . . . ?
C5 N1 C1 C2 -3.0(6) . . . . ?
Cu1 N1 C1 C2 174.8(3) . . . . ?
C5 N1 C1 P1 178.0(3) . . . . ?
Cu1 N1 C1 P1 -4.3(4) . . . . ?
C3 C2 C1 N1 1.9(6) . . . . ?
C3 C2 C1 P1 -179.0(3) . . . . ?
O1 P1 C1 N1 -176.3(3) . . . . ?
C6 P1 C1 N1 59.0(4) . . . . ?
C11 P1 C1 N1 -51.9(4) . . . . ?
O1 P1 C1 C2 4.6(4) . . . . ?
C6 P1 C1 C2 -120.1(4) . . . . ?
C11 P1 C1 C2 129.0(3) . . . . ?
C15 N3 C11 C12 -0.1(6) . . . . ?
Cu1 N3 C11 C12 -177.7(3) . . . . ?
C15 N3 C11 P1 179.7(3) . . . . ?
Cu1 N3 C11 P1 2.0(4) . . . . ?
O1 P1 C11 N3 178.5(3) . . . . ?
C6 P1 C11 N3 -57.6(4) . . . . ?
C1 P1 C11 N3 53.9(4) . . . . ?
O1 P1 C11 C12 -1.7(4) . . . . ?
C6 P1 C11 C12 122.2(3) . . . . ?
C1 P1 C11 C12 -126.3(3) . . . . ?
N3 C11 C12 C13 1.3(6) . . . . ?
P1 C11 C12 C13 -178.4(3) . . . . ?
C26 N6 C30 C29 0.8(6) . . . . ?
Cu2 N6 C30 C29 -171.8(3) . . . . ?
C28 C29 C30 N6 -0.8(7) . . . . ?
N1 C5 C4 C3 2.3(7) . . . . ?
C2 C3 C4 C5 -3.3(6) . . . . ?
N6 C26 C27 C28 -1.3(7) . . . . ?
P2 C26 C27 C28 177.1(3) . . . . ?
C25 N5 C21 C22 1.2(6) . . . . ?
Cu2 N5 C21 C22 -177.1(3) . . . . ?
C25 N5 C21 P2 -178.2(3) . . . . ?
Cu2 N5 C21 P2 3.5(4) . . . . ?
C23 C22 C21 N5 0.2(7) . . . . ?
C23 C22 C21 P2 179.6(3) . . . . ?
O2 P2 C21 N5 177.4(3) . . . . ?
C16 P2 C21 N5 -58.9(4) . . . . ?
C26 P2 C21 N5 52.3(4) . . . . ?
O2 P2 C21 C22 -2.1(4) . . . . ?
C16 P2 C21 C22 121.6(4) . . . . ?
C26 P2 C21 C22 -127.2(4) . . . . ?
C6 N2 C10 C9 -1.0(6) . . . . ?
Cu1 N2 C10 C9 176.9(3) . . . . ?
C8 C9 C10 N2 0.7(6) . . . . ?
N2 C6 C7 C8 -1.3(6) . . . . ?
P1 C6 C7 C8 -179.4(3) . . . . ?
C9 C8 C7 C6 0.9(6) . . . . ?
C20 N4 C16 C17 -1.6(6) . . . . ?
Cu2 N4 C16 C17 176.0(3) . . . . ?
C20 N4 C16 P2 177.4(3) . . . . ?
Cu2 N4 C16 P2 -5.0(4) . . . . ?
C18 C17 C16 N4 0.9(6) . . . . ?
C18 C17 C16 P2 -178.1(3) . . . . ?
O2 P2 C16 N4 -177.5(3) . . . . ?
C26 P2 C16 N4 -53.4(3) . . . . ?
C21 P2 C16 N4 59.5(3) . . . . ?
O2 P2 C16 C17 1.5(4) . . . . ?
C26 P2 C16 C17 125.6(3) . . . . ?
C21 P2 C16 C17 -121.5(3) . . . . ?
C21 N5 C25 C24 -0.5(6) . . . . ?
Cu2 N5 C25 C24 177.5(3) . . . . ?
C23 C24 C25 N5 -1.5(7) . . . . ?
C11 N3 C15 C14 -0.4(6) . . . . ?
Cu1 N3 C15 C14 177.0(3) . . . . ?
C13 C14 C15 N3 -0.4(7) . . . . ?
C11 C12 C13 C14 -2.1(7) . . . . ?
C15 C14 C13 C12 1.7(7) . . . . ?
C26 C27 C28 C29 1.2(7) . . . . ?
C30 C29 C28 C27 -0.2(7) . . . . ?
C21 C22 C23 C24 -2.2(7) . . . . ?
C25 C24 C23 C22 2.8(7) . . . . ?
C20 C19 C18 C17 -1.3(6) . . . . ?
C16 C17 C18 C19 0.6(6) . . . . ?

_refine_diff_density_max         1.752
_refine_diff_density_min         -1.633
_refine_diff_density_rms         0.198

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_tgn356
_audit_contact_author            'Joerg Sundermeyer'
_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
Bromo tris(2-pyridyl)phosphineoxide copper(I)
;
_chemical_name_common            'C2; CuBrtpypo'
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 Br1 Cu1 N3 O1 P1, 0.75(C2 H3 N)'
_chemical_formula_sum            'C16.50 H14.25 Br Cu N3.75 O P'
_chemical_formula_weight         455.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'
Br Br -0.2901 2.4595 '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                   8.5684(10)
_cell_length_b                   28.964(3)
_cell_length_c                   14.501(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.175(5)
_cell_angle_gamma                90
_cell_volume                     3456.3(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7651
_cell_measurement_theta_min      2.03
_cell_measurement_theta_max      27.17

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_F_000             1812
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    3.679
_shelx_estimated_absorpt_T_min   0.288
_shelx_estimated_absorpt_T_max   0.646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5766
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   
;
Bruker: SADABS v2012/1, Bruker AXS Inc., 
Madison, Wisconsin, USA, 2012.
;

_exptl_special_details           ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS Microfocus Source'
_diffrn_measurement_device_type  'D8 Quest (Bruker AXS Inc.)'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            21656
_diffrn_reflns_av_unetI/netI     0.1498
_diffrn_reflns_av_R_equivalents  0.1277
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.029
_diffrn_reflns_theta_max         27.166
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7647
_reflns_number_gt                4427
_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       
;
Bruker: Bruker Instrument Service v3.0.26, Bruker AXS Inc., 
Madison, Wisconsin, USA, 2012.
;
_computing_cell_refinement       
;
Bruker: APEX2 v2013.10-0, Bruker AXS Inc., 
Madison, Wisconsin, USA, 2012.
;
_computing_data_reduction        
;
Bruker: SAINT V8.27B, Bruker AXS Inc., 
Madison, Wisconsin, USA, 2012.
;
_computing_structure_solution    
;
SIR97 (A. Altomare, M. C. Burla, M. Camalli, G. Cascarano, C. Giacovazzo, 
A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, 
J. Appl. Crystallogr. 1999, 32, 115-119.)
;
_computing_structure_refinement  
;
SHELXL-2014 (G. Sheldrick, Acta Cryst. A 2008, 64, 112-122)
;
_computing_molecular_graphics    
;
K. Brandenburg, H. Putz: 
Diamond - Crystal and Molecular Structure Visualization v3.2i, 
Crystal Impact GbR, Bonn, Germany, 2012
;
_computing_publication_material  
;
WinGX publication routines (L. Farrugia, 
J. Appl. Crystallogr. 1999, 32, 837-838.)
;
_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)+(0.0302P)²+0.9489P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7647
_refine_ls_number_parameters     429
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1393
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_ref         0.1068
_refine_ls_wR_factor_gt          0.0912
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.005
_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
C11 C 0.3581(7) 0.5783(2) 0.6766(4) 0.0125(14) Uani 1 1 d . . . . .
C12 C 0.3305(7) 0.6182(2) 0.6221(4) 0.0164(14) Uani 1 1 d . . . . .
H12 H 0.3997 0.6442 0.6401 0.020 Uiso 1 1 calc R U . . .
C13 C 0.2001(8) 0.6193(2) 0.5410(5) 0.0242(17) Uani 1 1 d . . . . .
H13 H 0.1802 0.6459 0.5012 0.029 Uiso 1 1 calc R U . . .
C14 C 0.0998(8) 0.5819(2) 0.5182(5) 0.0287(18) Uani 1 1 d . . . . .
H14 H 0.0089 0.5822 0.4630 0.034 Uiso 1 1 calc R U . . .
C15 C 0.1332(8) 0.5435(2) 0.5772(5) 0.0272(17) Uani 1 1 d . . . . .
H15 H 0.0621 0.5177 0.5618 0.033 Uiso 1 1 calc R U . . .
C1 C 0.6508(7) 0.5269(2) 0.7640(4) 0.0112(13) Uani 1 1 d . . . . .
C2 C 0.8132(7) 0.5332(2) 0.7697(4) 0.0133(14) Uani 1 1 d . . . . .
H2 H 0.8641 0.5624 0.7855 0.016 Uiso 1 1 calc R U . . .
C3 C 0.8987(7) 0.4954(2) 0.7516(4) 0.0173(15) Uani 1 1 d . . . . .
H3 H 1.0103 0.4984 0.7546 0.021 Uiso 1 1 calc R U . . .
C4 C 0.8213(7) 0.4528(2) 0.7291(4) 0.0156(14) Uani 1 1 d . . . . .
H4 H 0.8784 0.4266 0.7162 0.019 Uiso 1 1 calc R U . . .
C5 C 0.6582(7) 0.4501(2) 0.7261(4) 0.0186(15) Uani 1 1 d . . . . .
H5 H 0.6041 0.4212 0.7117 0.022 Uiso 1 1 calc R U . . .
C6 C 0.4443(6) 0.55857(19) 0.8798(4) 0.0097(8) Uani 1 1 d . . . . .
C7 C 0.4773(7) 0.58495(19) 0.9634(4) 0.0120(13) Uani 1 1 d . . . . .
H7 H 0.5474 0.6109 0.9712 0.014 Uiso 1 1 calc R U . . .
C8 C 0.4060(7) 0.5726(2) 1.0354(4) 0.0157(14) Uani 1 1 d . . . . .
H8 H 0.4272 0.5898 1.0935 0.019 Uiso 1 1 calc R U . . .
C9 C 0.3037(7) 0.5349(2) 1.0200(4) 0.0134(14) Uani 1 1 d . . . . .
H9 H 0.2497 0.5264 1.0665 0.016 Uiso 1 1 calc R U . . .
C10 C 0.2804(6) 0.5096(2) 0.9367(4) 0.0122(13) Uani 1 1 d . . . . .
H10 H 0.2127 0.4831 0.9282 0.015 Uiso 1 1 calc R U . . .
C21 C -0.1344(6) 0.6694(2) 0.7051(4) 0.0105(13) Uani 1 1 d . . . . .
C22 C -0.1687(7) 0.6395(2) 0.6293(4) 0.0171(14) Uani 1 1 d . . . . .
H22 H -0.1064 0.6121 0.6320 0.020 Uiso 1 1 calc R U . . .
C23 C -0.2945(8) 0.6493(2) 0.5486(4) 0.0211(16) Uani 1 1 d . . . . .
H23 H -0.3205 0.6290 0.4950 0.025 Uiso 1 1 calc R U . . .
C24 C -0.3819(7) 0.6897(2) 0.5484(4) 0.0196(15) Uani 1 1 d . . . . .
H24 H -0.4679 0.6977 0.4936 0.024 Uiso 1 1 calc R U . . .
C25 C -0.3438(7) 0.7184(2) 0.6281(4) 0.0160(14) Uani 1 1 d . . . . .
H25 H -0.4068 0.7454 0.6278 0.019 Uiso 1 1 calc R U . . .
C16 C 0.1751(7) 0.70647(19) 0.8175(4) 0.0088(13) Uani 1 1 d . . . . .
C17 C 0.3341(6) 0.6998(2) 0.8172(4) 0.0111(13) Uani 1 1 d . . . . .
H17 H 0.3741 0.6695 0.8128 0.013 Uiso 1 1 calc R U . . .
C18 C 0.4339(7) 0.7373(2) 0.8234(4) 0.0160(15) Uani 1 1 d . . . . .
H18 H 0.5449 0.7334 0.8253 0.019 Uiso 1 1 calc R U . . .
C19 C 0.3703(7) 0.7809(2) 0.8266(4) 0.0143(14) Uani 1 1 d . . . . .
H19 H 0.4363 0.8075 0.8296 0.017 Uiso 1 1 calc R U . . .
C20 C 0.2085(6) 0.7852(2) 0.8255(4) 0.0097(8) Uani 1 1 d . . . . .
H20 H 0.1654 0.8153 0.8275 0.012 Uiso 1 1 calc R U . . .
C26 C -0.0385(6) 0.66359(19) 0.9154(4) 0.0097(8) Uani 1 1 d . . . . .
C27 C -0.0120(6) 0.6282(2) 0.9814(4) 0.0137(14) Uani 1 1 d . . . . .
H27 H 0.0423 0.6008 0.9716 0.016 Uiso 1 1 calc R U . . .
C28 C -0.0662(7) 0.6332(2) 1.0625(4) 0.0175(15) Uani 1 1 d . . . . .
H28 H -0.0499 0.6092 1.1089 0.021 Uiso 1 1 calc R U . . .
C29 C -0.1430(7) 0.6729(2) 1.0748(4) 0.0195(15) Uani 1 1 d . . . . .
H29 H -0.1812 0.6770 1.1298 0.023 Uiso 1 1 calc R U . . .
C30 C -0.1648(6) 0.7074(2) 1.0051(4) 0.0152(14) Uani 1 1 d . . . . .
H30 H -0.2189 0.7350 1.0140 0.018 Uiso 1 1 calc R U . . .
C31 C -0.0815(9) 0.8057(2) 0.5925(5) 0.041(2) Uani 1 1 d . . . . .
H31A H -0.0023 0.8310 0.6051 0.062 Uiso 1 1 calc R U . . .
H31B H -0.1340 0.8042 0.6444 0.062 Uiso 1 1 calc R U . . .
H31C H -0.1638 0.8113 0.5314 0.062 Uiso 1 1 calc R U . . .
C32 C 0.0002(8) 0.7628(2) 0.5874(5) 0.0221(16) Uani 1 1 d . . . . .
C34 C 0.558(2) 0.5063(6) 0.5149(13) 0.038(3) Uani 0.5 1 d . . P A -1
N8 N 0.6568(16) 0.5333(5) 0.5296(10) 0.038(3) Uani 0.5 1 d . . P A -1
C33 C 0.441(2) 0.4698(6) 0.4986(14) 0.038(3) Uani 0.5 1 d . . P A -1
H33A H 0.4861 0.4424 0.4754 0.057 Uiso 0.5 1 calc R U P A -1
H33B H 0.3420 0.4795 0.4505 0.057 Uiso 0.5 1 calc R U P A -1
H33C H 0.4162 0.4623 0.5588 0.057 Uiso 0.5 1 calc R U P A -1
N3 N 0.2607(6) 0.54106(17) 0.6547(3) 0.0163(12) Uani 1 1 d . . . . .
N1 N 0.5737(5) 0.48700(16) 0.7429(3) 0.0100(11) Uani 1 1 d . . . . .
N2 N 0.3497(5) 0.52087(16) 0.8666(3) 0.0100(11) Uani 1 1 d . . . . .
N5 N -0.2189(5) 0.70876(16) 0.7064(3) 0.0109(11) Uani 1 1 d . . . . .
N4 N 0.1115(5) 0.74934(16) 0.8216(3) 0.0093(11) Uani 1 1 d . . . . .
N6 N -0.1129(5) 0.70343(16) 0.9261(3) 0.0095(11) Uani 1 1 d . . . . .
N7 N 0.0672(7) 0.7295(2) 0.5816(4) 0.0282(14) Uani 1 1 d . . . . .
O1 O 0.6207(4) 0.61979(13) 0.8037(3) 0.0165(10) Uani 1 1 d . . . . .
O2 O 0.1127(4) 0.61275(13) 0.8052(3) 0.0152(10) Uani 1 1 d . . . . .
P1 P 0.52926(18) 0.57590(5) 0.78385(11) 0.0107(3) Uani 1 1 d . . . . .
P2 P 0.03638(18) 0.65810(5) 0.80927(11) 0.0104(3) Uani 1 1 d . . . . .
Cu1 Cu 0.33139(8) 0.48462(3) 0.74155(5) 0.01305(18) Uani 1 1 d . . . . .
Cu2 Cu -0.13029(8) 0.75171(2) 0.82107(5) 0.01166(18) Uani 1 1 d . . . . .
Br1 Br 0.23211(7) 0.40878(2) 0.72934(5) 0.01856(16) Uani 1 1 d . . . . .
Br2 Br -0.23371(7) 0.82711(2) 0.81408(4) 0.01469(15) 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
C11 N3 1.347(7) . ?
C11 C12 1.382(8) . ?
C11 P1 1.818(6) . ?
C12 C13 1.378(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.365(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(9) . ?
C14 H14 0.9500 . ?
C15 N3 1.333(7) . ?
C15 H15 0.9500 . ?
C1 N1 1.325(7) . ?
C1 C2 1.383(7) . ?
C1 P1 1.830(6) . ?
C2 C3 1.383(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(8) . ?
C4 H4 0.9500 . ?
C5 N1 1.352(7) . ?
C5 H5 0.9500 . ?
C6 N2 1.342(7) . ?
C6 C7 1.393(8) . ?
C6 P1 1.812(6) . ?
C7 C8 1.396(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.380(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(8) . ?
C9 H9 0.9500 . ?
C10 N2 1.353(7) . ?
C10 H10 0.9500 . ?
C21 N5 1.353(7) . ?
C21 C22 1.366(8) . ?
C21 P2 1.817(6) . ?
C22 C23 1.381(8) . ?
C22 H22 0.9500 . ?
C23 C24 1.390(8) . ?
C23 H23 0.9500 . ?
C24 C25 1.386(8) . ?
C24 H24 0.9500 . ?
C25 N5 1.355(7) . ?
C25 H25 0.9500 . ?
C16 N4 1.364(7) . ?
C16 C17 1.377(7) . ?
C16 P2 1.819(6) . ?
C17 C18 1.370(8) . ?
C17 H17 0.9500 . ?
C18 C19 1.382(8) . ?
C18 H18 0.9500 . ?
C19 C20 1.388(7) . ?
C19 H19 0.9500 . ?
C20 N4 1.322(7) . ?
C20 H20 0.9500 . ?
C26 N6 1.348(7) . ?
C26 C27 1.378(8) . ?
C26 P2 1.831(6) . ?
C27 C28 1.386(8) . ?
C27 H27 0.9500 . ?
C28 C29 1.361(8) . ?
C28 H28 0.9500 . ?
C29 C30 1.396(8) . ?
C29 H29 0.9500 . ?
C30 N6 1.346(7) . ?
C30 H30 0.9500 . ?
C31 C32 1.438(9) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 N7 1.139(8) . ?
C34 N8 1.13(2) . ?
C34 C33 1.43(2) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
N3 Cu1 2.049(5) . ?
N1 Cu1 2.072(4) . ?
N2 Cu1 2.063(5) . ?
N5 Cu2 2.046(5) . ?
N4 Cu2 2.071(4) . ?
N6 Cu2 2.042(5) . ?
O1 P1 1.479(4) . ?
O2 P2 1.476(4) . ?
Cu1 Br1 2.3443(10) . ?
Cu2 Br2 2.3483(10) . ?

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
N3 C11 C12 122.6(6) . . ?
N3 C11 P1 118.0(4) . . ?
C12 C11 P1 119.4(5) . . ?
C13 C12 C11 118.4(6) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
C14 C13 C12 119.6(6) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 118.8(6) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
N3 C15 C14 122.8(6) . . ?
N3 C15 H15 118.6 . . ?
C14 C15 H15 118.6 . . ?
N1 C1 C2 123.9(5) . . ?
N1 C1 P1 116.4(4) . . ?
C2 C1 P1 119.7(4) . . ?
C1 C2 C3 117.5(5) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C2 C3 C4 120.2(5) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 117.8(5) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
N1 C5 C4 122.2(6) . . ?
N1 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
N2 C6 C7 122.6(5) . . ?
N2 C6 P1 118.1(4) . . ?
C7 C6 P1 119.2(4) . . ?
C6 C7 C8 119.1(6) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C9 C8 C7 118.2(6) . . ?
C9 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
C10 C9 C8 119.6(6) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
N2 C10 C9 122.9(6) . . ?
N2 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?
N5 C21 C22 123.4(5) . . ?
N5 C21 P2 116.7(4) . . ?
C22 C21 P2 119.9(4) . . ?
C21 C22 C23 119.6(6) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C22 C23 C24 117.9(6) . . ?
C22 C23 H23 121.1 . . ?
C24 C23 H23 121.1 . . ?
C25 C24 C23 120.1(6) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
N5 C25 C24 121.5(6) . . ?
N5 C25 H25 119.2 . . ?
C24 C25 H25 119.2 . . ?
N4 C16 C17 122.4(5) . . ?
N4 C16 P2 116.2(4) . . ?
C17 C16 P2 121.4(4) . . ?
C18 C17 C16 119.3(5) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C17 C18 C19 118.8(5) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C18 C19 C20 119.0(5) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
N4 C20 C19 122.9(5) . . ?
N4 C20 H20 118.5 . . ?
C19 C20 H20 118.5 . . ?
N6 C26 C27 123.2(5) . . ?
N6 C26 P2 117.3(4) . . ?
C27 C26 P2 119.4(4) . . ?
C26 C27 C28 118.9(6) . . ?
C26 C27 H27 120.6 . . ?
C28 C27 H27 120.6 . . ?
C29 C28 C27 119.2(6) . . ?
C29 C28 H28 120.4 . . ?
C27 C28 H28 120.4 . . ?
C28 C29 C30 118.8(6) . . ?
C28 C29 H29 120.6 . . ?
C30 C29 H29 120.6 . . ?
N6 C30 C29 123.1(6) . . ?
N6 C30 H30 118.5 . . ?
C29 C30 H30 118.5 . . ?
C32 C31 H31A 109.5 . . ?
C32 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C32 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N7 C32 C31 177.9(7) . . ?
N8 C34 C33 176(2) . . ?
C34 C33 H33A 109.5 . . ?
C34 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C34 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C15 N3 C11 117.7(5) . . ?
C15 N3 Cu1 126.3(4) . . ?
C11 N3 Cu1 115.9(4) . . ?
C1 N1 C5 118.4(5) . . ?
C1 N1 Cu1 117.7(4) . . ?
C5 N1 Cu1 123.9(4) . . ?
C6 N2 C10 117.6(5) . . ?
C6 N2 Cu1 115.8(4) . . ?
C10 N2 Cu1 126.6(4) . . ?
C21 N5 C25 117.5(5) . . ?
C21 N5 Cu2 116.4(4) . . ?
C25 N5 Cu2 125.7(4) . . ?
C20 N4 C16 117.6(5) . . ?
C20 N4 Cu2 126.2(4) . . ?
C16 N4 Cu2 116.2(4) . . ?
C30 N6 C26 116.8(5) . . ?
C30 N6 Cu2 127.2(4) . . ?
C26 N6 Cu2 116.0(4) . . ?
O1 P1 C6 113.2(3) . . ?
O1 P1 C11 113.0(3) . . ?
C6 P1 C11 105.5(3) . . ?
O1 P1 C1 113.8(2) . . ?
C6 P1 C1 105.9(3) . . ?
C11 P1 C1 104.7(3) . . ?
O2 P2 C21 113.0(3) . . ?
O2 P2 C16 113.5(2) . . ?
C21 P2 C16 106.0(3) . . ?
O2 P2 C26 111.9(2) . . ?
C21 P2 C26 107.1(3) . . ?
C16 P2 C26 104.7(3) . . ?
N3 Cu1 N2 94.09(19) . . ?
N3 Cu1 N1 95.91(19) . . ?
N2 Cu1 N1 98.29(18) . . ?
N3 Cu1 Br1 131.45(14) . . ?
N2 Cu1 Br1 118.71(13) . . ?
N1 Cu1 Br1 111.93(13) . . ?
N6 Cu2 N5 97.06(19) . . ?
N6 Cu2 N4 96.27(18) . . ?
N5 Cu2 N4 97.31(18) . . ?
N6 Cu2 Br2 128.13(14) . . ?
N5 Cu2 Br2 118.71(13) . . ?
N4 Cu2 Br2 113.33(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 C11 C12 C13 -1.5(9) . . . . ?
P1 C11 C12 C13 179.9(4) . . . . ?
C11 C12 C13 C14 1.9(9) . . . . ?
C12 C13 C14 C15 -0.7(10) . . . . ?
C13 C14 C15 N3 -1.1(10) . . . . ?
N1 C1 C2 C3 0.4(9) . . . . ?
P1 C1 C2 C3 -178.3(4) . . . . ?
C1 C2 C3 C4 -0.3(9) . . . . ?
C2 C3 C4 C5 -0.3(9) . . . . ?
C3 C4 C5 N1 0.9(9) . . . . ?
N2 C6 C7 C8 -1.8(8) . . . . ?
P1 C6 C7 C8 177.3(4) . . . . ?
C6 C7 C8 C9 -0.7(8) . . . . ?
C7 C8 C9 C10 2.6(8) . . . . ?
C8 C9 C10 N2 -2.2(9) . . . . ?
N5 C21 C22 C23 0.6(9) . . . . ?
P2 C21 C22 C23 -177.3(5) . . . . ?
C21 C22 C23 C24 -0.1(9) . . . . ?
C22 C23 C24 C25 -1.2(9) . . . . ?
C23 C24 C25 N5 2.0(9) . . . . ?
N4 C16 C17 C18 1.4(9) . . . . ?
P2 C16 C17 C18 179.9(4) . . . . ?
C16 C17 C18 C19 -2.0(9) . . . . ?
C17 C18 C19 C20 1.2(9) . . . . ?
C18 C19 C20 N4 0.2(9) . . . . ?
N6 C26 C27 C28 0.9(8) . . . . ?
P2 C26 C27 C28 178.6(4) . . . . ?
C26 C27 C28 C29 -0.3(8) . . . . ?
C27 C28 C29 C30 0.0(9) . . . . ?
C28 C29 C30 N6 -0.2(9) . . . . ?
C14 C15 N3 C11 1.5(9) . . . . ?
C14 C15 N3 Cu1 -175.3(5) . . . . ?
C12 C11 N3 C15 -0.2(9) . . . . ?
P1 C11 N3 C15 178.4(4) . . . . ?
C12 C11 N3 Cu1 177.0(4) . . . . ?
P1 C11 N3 Cu1 -4.4(6) . . . . ?
C2 C1 N1 C5 0.1(9) . . . . ?
P1 C1 N1 C5 178.9(4) . . . . ?
C2 C1 N1 Cu1 178.4(4) . . . . ?
P1 C1 N1 Cu1 -2.8(6) . . . . ?
C4 C5 N1 C1 -0.8(9) . . . . ?
C4 C5 N1 Cu1 -179.0(4) . . . . ?
C7 C6 N2 C10 2.3(8) . . . . ?
P1 C6 N2 C10 -176.8(4) . . . . ?
C7 C6 N2 Cu1 -175.7(4) . . . . ?
P1 C6 N2 Cu1 5.2(5) . . . . ?
C9 C10 N2 C6 -0.3(8) . . . . ?
C9 C10 N2 Cu1 177.5(4) . . . . ?
C22 C21 N5 C25 0.2(8) . . . . ?
P2 C21 N5 C25 178.2(4) . . . . ?
C22 C21 N5 Cu2 -173.5(5) . . . . ?
P2 C21 N5 Cu2 4.5(5) . . . . ?
C24 C25 N5 C21 -1.5(8) . . . . ?
C24 C25 N5 Cu2 171.5(4) . . . . ?
C19 C20 N4 C16 -0.8(8) . . . . ?
C19 C20 N4 Cu2 179.3(4) . . . . ?
C17 C16 N4 C20 0.0(8) . . . . ?
P2 C16 N4 C20 -178.5(4) . . . . ?
C17 C16 N4 Cu2 179.9(4) . . . . ?
P2 C16 N4 Cu2 1.4(5) . . . . ?
C29 C30 N6 C26 0.8(8) . . . . ?
C29 C30 N6 Cu2 -178.0(4) . . . . ?
C27 C26 N6 C30 -1.1(8) . . . . ?
P2 C26 N6 C30 -178.9(4) . . . . ?
C27 C26 N6 Cu2 177.7(4) . . . . ?
P2 C26 N6 Cu2 0.0(5) . . . . ?
N2 C6 P1 O1 175.6(4) . . . . ?
C7 C6 P1 O1 -3.6(5) . . . . ?
N2 C6 P1 C11 51.6(5) . . . . ?
C7 C6 P1 C11 -127.6(5) . . . . ?
N2 C6 P1 C1 -59.1(5) . . . . ?
C7 C6 P1 C1 121.7(5) . . . . ?
N3 C11 P1 O1 -176.4(4) . . . . ?
C12 C11 P1 O1 2.3(6) . . . . ?
N3 C11 P1 C6 -52.2(5) . . . . ?
C12 C11 P1 C6 126.4(5) . . . . ?
N3 C11 P1 C1 59.3(5) . . . . ?
C12 C11 P1 C1 -122.1(5) . . . . ?
N1 C1 P1 O1 -177.9(4) . . . . ?
C2 C1 P1 O1 0.9(6) . . . . ?
N1 C1 P1 C6 57.1(5) . . . . ?
C2 C1 P1 C6 -124.0(5) . . . . ?
N1 C1 P1 C11 -54.1(5) . . . . ?
C2 C1 P1 C11 124.8(5) . . . . ?
N5 C21 P2 O2 175.2(4) . . . . ?
C22 C21 P2 O2 -6.8(6) . . . . ?
N5 C21 P2 C16 -59.8(5) . . . . ?
C22 C21 P2 C16 118.2(5) . . . . ?
N5 C21 P2 C26 51.5(5) . . . . ?
C22 C21 P2 C26 -130.4(5) . . . . ?
N4 C16 P2 O2 -179.9(4) . . . . ?
C17 C16 P2 O2 1.6(6) . . . . ?
N4 C16 P2 C21 55.5(5) . . . . ?
C17 C16 P2 C21 -123.1(5) . . . . ?
N4 C16 P2 C26 -57.6(5) . . . . ?
C17 C16 P2 C26 123.9(5) . . . . ?
N6 C26 P2 O2 -179.1(4) . . . . ?
C27 C26 P2 O2 3.1(5) . . . . ?
N6 C26 P2 C21 -54.7(5) . . . . ?
C27 C26 P2 C21 127.4(5) . . . . ?
N6 C26 P2 C16 57.5(5) . . . . ?
C27 C26 P2 C16 -120.3(5) . . . . ?

_refine_diff_density_max         0.820
_refine_diff_density_min         -0.772
_refine_diff_density_rms         0.159

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
_database_code_depnum_ccdc_archive 'CCDC 1021438'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_tgn343
_database_code_depnum_ccdc_archive 'CCDC 1021439'
_audit_contact_author            'Joerg Sundermeyer'
_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
Iodo tris(2-pyridyl)phosphineoxide copper(I)
;
_chemical_name_common            'C3, CuItpypo'
_chemical_melting_point          ?
_chemical_formula_moiety         ' C15 H12 Cu I N3 O P, 0.75(C2 H3 N)'
_chemical_formula_sum            'C16.50 H14.25 Cu I N3.75 O P'
_chemical_formula_weight         502.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'

_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                   8.6959(3)
_cell_length_b                   29.6332(11)
_cell_length_c                   14.5579(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.894(3)
_cell_angle_gamma                90
_cell_volume                     3608.0(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    17620
_cell_measurement_theta_min      2
_cell_measurement_theta_max      27.11

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.850
_exptl_crystal_F_000             1956
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    3.021
_shelx_estimated_absorpt_T_min   0.570
_shelx_estimated_absorpt_T_max   0.889
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.6549
_exptl_absorpt_correction_T_max  0.9041
_exptl_absorpt_process_details   
; 
 N.W. Alcock (1970). Cryst. Computing, p271
;

_exptl_special_details           ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            33130
_diffrn_reflns_av_unetI/netI     0.1062
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.374
_diffrn_reflns_theta_max         26.730
_diffrn_reflns_theta_full        25.000
_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             7632
_reflns_number_gt                4265
_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       
;
Stoe & Cie: X-AREA v1.56, Stoe & Cie GmbH, Darmstadt, Germany, 2011
;
_computing_cell_refinement       
;
Stoe & Cie: X-AREA v1.56, Stoe & Cie GmbH, Darmstadt, Germany, 2011
;
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    
;
SIR97 (A. Altomare, M. C. Burla, M. Camalli, G. Cascarano, C. Giacovazzo, 
A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, 
J. Appl. Crystallogr. 1999, 32, 115-119.)
;
_computing_structure_refinement  
;
SHELXL-2014 (G. Sheldrick, Acta Cryst. A 2008, 64, 112-122)
;
_computing_molecular_graphics    
;
K. Brandenburg, H. Putz: 
Diamond - Crystal and Molecular Structure Visualization v3.2i, 
Crystal Impact GbR, Bonn, Germany, 2012
;
_computing_publication_material  
;
WinGX publication routines (L. Farrugia, 
J. Appl. Crystallogr. 1999, 32, 837-838.)
;

_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)+(0.0142P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7632
_refine_ls_number_parameters     453
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0492
_refine_ls_wR_factor_gt          0.0451
_refine_ls_goodness_of_fit_ref   0.689
_refine_ls_restrained_S_all      0.689
_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
N1 N -0.0800(4) 0.49028(12) 0.7543(2) 0.0237(8) Uani 1 1 d . . . . .
C5 C -0.1671(5) 0.45566(16) 0.7708(3) 0.0292(11) Uani 1 1 d . . . . .
H5 H -0.1172 0.4270 0.7851 0.035 Uiso 1 1 calc R U . . .
C4 C -0.3272(6) 0.45969(16) 0.7681(3) 0.0333(12) Uani 1 1 d . . . . .
H4 H -0.3848 0.4345 0.7818 0.040 Uiso 1 1 calc R U . . .
C3 C -0.4012(5) 0.50083(16) 0.7451(3) 0.0300(11) Uani 1 1 d . . . . .
H3 H -0.5114 0.5042 0.7413 0.036 Uiso 1 1 calc R U . . .
C2 C -0.3142(5) 0.53710(16) 0.7275(3) 0.0284(11) Uani 1 1 d . . . . .
H2 H -0.3631 0.5658 0.7118 0.034 Uiso 1 1 calc R U . . .
N2 N 0.1431(4) 0.52235(12) 0.6316(2) 0.0243(9) Uani 1 1 d . . . . .
C10 C 0.2116(5) 0.51058(15) 0.5629(3) 0.0267(10) Uani 1 1 d . . . . .
H10 H 0.2736 0.4837 0.5710 0.032 Uiso 1 1 calc R U . . .
C9 C 0.1957(5) 0.53588(15) 0.4810(3) 0.0284(11) Uani 1 1 d . . . . .
H9 H 0.2499 0.5273 0.4353 0.034 Uiso 1 1 calc R U . . .
C8 C 0.1003(5) 0.57365(16) 0.4666(3) 0.0293(11) Uani 1 1 d . . . . .
H8 H 0.0842 0.5908 0.4096 0.035 Uiso 1 1 calc R U . . .
C7 C 0.0282(5) 0.58634(16) 0.5365(3) 0.0257(10) Uani 1 1 d . . . . .
H7 H -0.0371 0.6125 0.5289 0.031 Uiso 1 1 calc R U . . .
N3 N 0.2287(4) 0.54142(13) 0.8432(3) 0.0305(9) Uani 1 1 d . . . . .
C15 C 0.3524(6) 0.54306(18) 0.9213(3) 0.0378(12) Uani 1 1 d . . . . .
H15 H 0.4169 0.5169 0.9383 0.045 Uiso 1 1 calc R U . . .
C14 C 0.3913(7) 0.58063(18) 0.9784(3) 0.0432(14) Uani 1 1 d . . . . .
H14 H 0.4813 0.5803 1.0329 0.052 Uiso 1 1 calc R U . . .
C13 C 0.2979(6) 0.61891(18) 0.9555(3) 0.0375(13) Uani 1 1 d . . . . .
H13 H 0.3217 0.6452 0.9942 0.045 Uiso 1 1 calc R U . . .
C12 C 0.1687(6) 0.61810(15) 0.8749(3) 0.0292(11) Uani 1 1 d . . . . .
H12 H 0.1020 0.6438 0.8572 0.035 Uiso 1 1 calc R U . . .
C26 C 0.5394(5) 0.66387(14) 0.5893(3) 0.0226(10) Uani 1 1 d . . . . .
C27 C 0.5133(5) 0.62914(16) 0.5239(3) 0.0270(10) Uani 1 1 d . . . . .
H27 H 0.4614 0.6022 0.5344 0.032 Uiso 1 1 calc R U . . .
C28 C 0.5651(6) 0.63447(17) 0.4417(3) 0.0347(12) Uani 1 1 d . . . . .
H28 H 0.5486 0.6113 0.3949 0.042 Uiso 1 1 calc R U . . .
C29 C 0.6409(5) 0.67430(17) 0.4299(3) 0.0309(11) Uani 1 1 d . . . . .
H29 H 0.6782 0.6787 0.3750 0.037 Uiso 1 1 calc R U . . .
C30 C 0.6618(5) 0.70763(17) 0.4990(3) 0.0302(11) Uani 1 1 d . . . . .
H30 H 0.7134 0.7349 0.4899 0.036 Uiso 1 1 calc R U . . .
C21 C 0.6348(5) 0.66901(15) 0.7977(3) 0.0227(9) Uani 1 1 d . . . . .
C22 C 0.6709(5) 0.63891(16) 0.8730(3) 0.0285(11) Uani 1 1 d . . . . .
H22 H 0.6117 0.6118 0.8707 0.034 Uiso 1 1 calc R U . . .
C23 C 0.7967(6) 0.64949(17) 0.9524(3) 0.0348(12) Uani 1 1 d . . . . .
H23 H 0.8237 0.6298 1.0059 0.042 Uiso 1 1 calc R U . . .
C24 C 0.8814(6) 0.68867(16) 0.9529(3) 0.0317(11) Uani 1 1 d . . . . .
H24 H 0.9682 0.6963 1.0061 0.038 Uiso 1 1 calc R U . . .
C25 C 0.8375(5) 0.71673(16) 0.8741(3) 0.0306(11) Uani 1 1 d . . . . .
H25 H 0.8968 0.7437 0.8744 0.037 Uiso 1 1 calc R U . . .
C16 C 0.3302(5) 0.70468(15) 0.6863(3) 0.0231(10) Uani 1 1 d . . . . .
C17 C 0.1717(5) 0.69745(16) 0.6850(3) 0.0263(11) Uani 1 1 d . . . . .
H17 H 0.1324 0.6677 0.6880 0.032 Uiso 1 1 calc R U . . .
C18 C 0.0722(5) 0.73439(16) 0.6792(3) 0.0279(11) Uani 1 1 d . . . . .
H18 H -0.0365 0.7304 0.6785 0.034 Uiso 1 1 calc R U . . .
C19 C 0.1331(5) 0.77722(15) 0.6744(3) 0.0274(11) Uani 1 1 d . . . . .
H19 H 0.0669 0.8031 0.6701 0.033 Uiso 1 1 calc R U . . .
C20 C 0.2922(5) 0.78170(15) 0.6760(3) 0.0266(11) Uani 1 1 d . . . . .
H20 H 0.3333 0.8111 0.6723 0.032 Uiso 1 1 calc R U . . .
C31 C 0.5733(8) 0.8013(2) 0.9170(4) 0.0576(17) Uani 1 1 d . . . . .
H31A H 0.6049 0.8032 0.8575 0.086 Uiso 1 1 calc R U . . .
H31B H 0.6688 0.8026 0.9716 0.086 Uiso 1 1 calc R U . . .
H31C H 0.5026 0.8267 0.9204 0.086 Uiso 1 1 calc R U . . .
C32 C 0.4898(6) 0.75925(19) 0.9194(3) 0.0383(13) Uani 1 1 d . . . . .
C1 C -0.1535(5) 0.53085(15) 0.7333(3) 0.0249(10) Uani 1 1 d . . . . .
C6 C 0.0540(5) 0.55988(15) 0.6175(3) 0.0232(10) Uani 1 1 d . . . . .
C11 C 0.1385(5) 0.57916(15) 0.8206(3) 0.0259(11) Uani 1 1 d . . . . .
N6 N 0.6120(4) 0.70315(12) 0.5786(2) 0.0240(9) Uani 1 1 d . . . . .
N5 N 0.7149(4) 0.70777(12) 0.7973(2) 0.0242(8) Uani 1 1 d . . . . .
N4 N 0.3911(4) 0.74635(12) 0.6826(2) 0.0234(8) Uani 1 1 d . . . . .
N7 N 0.4198(6) 0.72659(16) 0.9194(3) 0.0441(11) Uani 1 1 d . . . . .
O1 O -0.1167(3) 0.62081(10) 0.6938(2) 0.0305(7) Uani 1 1 d . . . . .
O2 O 0.3916(3) 0.61323(10) 0.6984(2) 0.0270(7) Uani 1 1 d . . . . .
P1 P -0.02996(14) 0.57751(4) 0.71404(8) 0.0248(3) Uani 1 1 d . . . . .
P2 P 0.46644(14) 0.65752(4) 0.69473(8) 0.0234(3) Uani 1 1 d . . . . .
Cu1 Cu 0.15735(6) 0.48685(2) 0.75534(4) 0.02536(13) Uani 1 1 d . . . . .
Cu2 Cu 0.62852(6) 0.75013(2) 0.68345(4) 0.02407(13) Uani 1 1 d . . . . .
I1 I 0.26200(3) 0.40786(2) 0.77178(2) 0.02743(8) Uani 1 1 d . . . . .
I2 I 0.73719(3) 0.82887(2) 0.69298(2) 0.02620(7) Uani 1 1 d . . . . .
C34 C 0.0629(19) 0.4939(5) 0.0189(9) 0.041(4) Uani 0.5 1 d . . P A -1
N8 N 0.1491(17) 0.4643(5) 0.0306(8) 0.061(3) Uani 0.5 1 d . . P A -1
C33 C -0.0442(17) 0.5320(7) 0.0011(10) 0.044(3) Uani 0.5 1 d . . P A -1
H33A H 0.0174 0.5599 0.0032 0.066 Uiso 0.5 1 calc R U P A -1
H33B H -0.1023 0.5332 0.0501 0.066 Uiso 0.5 1 calc R U P A -1
H33C H -0.1206 0.5289 -0.0620 0.066 Uiso 0.5 1 calc R U P A -1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.336(5) . ?
N1 C1 1.357(5) . ?
N1 Cu1 2.062(3) . ?
C5 C4 1.387(6) . ?
C5 H5 0.9500 . ?
C4 C3 1.377(6) . ?
C4 H4 0.9500 . ?
C3 C2 1.378(6) . ?
C3 H3 0.9500 . ?
C2 C1 1.389(6) . ?
C2 H2 0.9500 . ?
N2 C6 1.339(5) . ?
N2 C10 1.342(5) . ?
N2 Cu1 2.060(3) . ?
C10 C9 1.383(6) . ?
C10 H10 0.9500 . ?
C9 C8 1.374(6) . ?
C9 H9 0.9500 . ?
C8 C7 1.386(6) . ?
C8 H8 0.9500 . ?
C7 C6 1.382(6) . ?
C7 H7 0.9500 . ?
N3 C15 1.335(6) . ?
N3 C11 1.354(6) . ?
N3 Cu1 2.049(4) . ?
C15 C14 1.375(7) . ?
C15 H15 0.9500 . ?
C14 C13 1.382(7) . ?
C14 H14 0.9500 . ?
C13 C12 1.385(7) . ?
C13 H13 0.9500 . ?
C12 C11 1.382(6) . ?
C12 H12 0.9500 . ?
C26 N6 1.353(5) . ?
C26 C27 1.378(6) . ?
C26 P2 1.824(4) . ?
C27 C28 1.399(6) . ?
C27 H27 0.9500 . ?
C28 C29 1.386(6) . ?
C28 H28 0.9500 . ?
C29 C30 1.386(6) . ?
C29 H29 0.9500 . ?
C30 N6 1.350(5) . ?
C30 H30 0.9500 . ?
C21 N5 1.344(5) . ?
C21 C22 1.381(6) . ?
C21 P2 1.818(4) . ?
C22 C23 1.392(7) . ?
C22 H22 0.9500 . ?
C23 C24 1.374(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.382(6) . ?
C24 H24 0.9500 . ?
C25 N5 1.344(6) . ?
C25 H25 0.9500 . ?
C16 N4 1.350(5) . ?
C16 C17 1.390(6) . ?
C16 P2 1.814(5) . ?
C17 C18 1.384(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.384(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.384(6) . ?
C19 H19 0.9500 . ?
C20 N4 1.342(5) . ?
C20 H20 0.9500 . ?
C31 C32 1.448(8) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 N7 1.143(6) . ?
C1 P1 1.820(4) . ?
C6 P1 1.829(4) . ?
C11 P1 1.820(5) . ?
N6 Cu2 2.042(4) . ?
N5 Cu2 2.050(4) . ?
N4 Cu2 2.065(3) . ?
O1 P1 1.477(3) . ?
O2 P2 1.473(3) . ?
Cu1 I1 2.4990(6) . ?
Cu2 I2 2.5068(6) . ?
C34 N8 1.134(17) . ?
C34 C33 1.44(2) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 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
C5 N1 C1 117.7(4) . . ?
C5 N1 Cu1 125.2(3) . . ?
C1 N1 Cu1 117.0(3) . . ?
N1 C5 C4 122.9(4) . . ?
N1 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C3 C4 C5 118.8(4) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C4 C3 C2 119.5(4) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C2 C1 118.6(4) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C6 N2 C10 117.2(4) . . ?
C6 N2 Cu1 116.9(3) . . ?
C10 N2 Cu1 125.9(3) . . ?
N2 C10 C9 122.8(4) . . ?
N2 C10 H10 118.6 . . ?
C9 C10 H10 118.6 . . ?
C8 C9 C10 119.1(4) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C9 C8 C7 118.9(4) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C6 C7 C8 118.2(4) . . ?
C6 C7 H7 120.9 . . ?
C8 C7 H7 120.9 . . ?
C15 N3 C11 117.0(4) . . ?
C15 N3 Cu1 126.6(3) . . ?
C11 N3 Cu1 116.4(3) . . ?
N3 C15 C14 123.5(5) . . ?
N3 C15 H15 118.2 . . ?
C14 C15 H15 118.2 . . ?
C15 C14 C13 119.2(5) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C13 C12 118.5(5) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C11 C12 C13 118.8(5) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
N6 C26 C27 123.8(4) . . ?
N6 C26 P2 117.8(3) . . ?
C27 C26 P2 118.4(3) . . ?
C26 C27 C28 118.5(4) . . ?
C26 C27 H27 120.8 . . ?
C28 C27 H27 120.8 . . ?
C29 C28 C27 118.5(4) . . ?
C29 C28 H28 120.7 . . ?
C27 C28 H28 120.7 . . ?
C28 C29 C30 119.3(4) . . ?
C28 C29 H29 120.4 . . ?
C30 C29 H29 120.4 . . ?
N6 C30 C29 123.0(4) . . ?
N6 C30 H30 118.5 . . ?
C29 C30 H30 118.5 . . ?
N5 C21 C22 123.4(4) . . ?
N5 C21 P2 117.2(3) . . ?
C22 C21 P2 119.3(3) . . ?
C21 C22 C23 118.0(4) . . ?
C21 C22 H22 121.0 . . ?
C23 C22 H22 121.0 . . ?
C24 C23 C22 119.5(4) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C23 C24 C25 118.6(5) . . ?
C23 C24 H24 120.7 . . ?
C25 C24 H24 120.7 . . ?
N5 C25 C24 123.2(4) . . ?
N5 C25 H25 118.4 . . ?
C24 C25 H25 118.4 . . ?
N4 C16 C17 122.6(4) . . ?
N4 C16 P2 116.8(3) . . ?
C17 C16 P2 120.6(3) . . ?
C18 C17 C16 118.7(4) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C17 C18 C19 119.1(4) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C20 C19 C18 118.8(4) . . ?
C20 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
N4 C20 C19 123.0(4) . . ?
N4 C20 H20 118.5 . . ?
C19 C20 H20 118.5 . . ?
C32 C31 H31A 109.5 . . ?
C32 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C32 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N7 C32 C31 177.9(6) . . ?
N1 C1 C2 122.4(4) . . ?
N1 C1 P1 116.5(3) . . ?
C2 C1 P1 121.1(4) . . ?
N2 C6 C7 123.6(4) . . ?
N2 C6 P1 117.1(3) . . ?
C7 C6 P1 119.2(3) . . ?
N3 C11 C12 123.0(5) . . ?
N3 C11 P1 117.5(3) . . ?
C12 C11 P1 119.5(4) . . ?
C30 N6 C26 117.0(4) . . ?
C30 N6 Cu2 126.9(3) . . ?
C26 N6 Cu2 116.1(2) . . ?
C25 N5 C21 117.3(4) . . ?
C25 N5 Cu2 125.7(3) . . ?
C21 N5 Cu2 116.8(3) . . ?
C20 N4 C16 117.8(4) . . ?
C20 N4 Cu2 125.3(3) . . ?
C16 N4 Cu2 116.8(3) . . ?
O1 P1 C1 113.57(19) . . ?
O1 P1 C11 113.3(2) . . ?
C1 P1 C11 105.1(2) . . ?
O1 P1 C6 112.63(19) . . ?
C1 P1 C6 106.16(19) . . ?
C11 P1 C6 105.4(2) . . ?
O2 P2 C16 113.71(19) . . ?
O2 P2 C21 113.65(19) . . ?
C16 P2 C21 106.0(2) . . ?
O2 P2 C26 112.43(18) . . ?
C16 P2 C26 103.59(19) . . ?
C21 P2 C26 106.68(19) . . ?
N3 Cu1 N2 94.48(14) . . ?
N3 Cu1 N1 95.57(14) . . ?
N2 Cu1 N1 98.53(14) . . ?
N3 Cu1 I1 129.72(11) . . ?
N2 Cu1 I1 119.68(10) . . ?
N1 Cu1 I1 112.60(10) . . ?
N6 Cu2 N5 97.00(14) . . ?
N6 Cu2 N4 95.33(14) . . ?
N5 Cu2 N4 96.67(14) . . ?
N6 Cu2 I2 128.63(10) . . ?
N5 Cu2 I2 118.42(10) . . ?
N4 Cu2 I2 114.34(10) . . ?
N8 C34 C33 177.8(14) . . ?
C34 C33 H33A 109.5 . . ?
C34 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C34 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 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
C1 N1 C5 C4 -0.5(6) . . . . ?
Cu1 N1 C5 C4 -179.1(3) . . . . ?
N1 C5 C4 C3 1.6(7) . . . . ?
C5 C4 C3 C2 -1.4(7) . . . . ?
C4 C3 C2 C1 0.2(7) . . . . ?
C6 N2 C10 C9 1.2(6) . . . . ?
Cu1 N2 C10 C9 179.3(3) . . . . ?
N2 C10 C9 C8 -2.9(7) . . . . ?
C10 C9 C8 C7 2.7(7) . . . . ?
C9 C8 C7 C6 -0.9(6) . . . . ?
C11 N3 C15 C14 -0.1(7) . . . . ?
Cu1 N3 C15 C14 -178.4(3) . . . . ?
N3 C15 C14 C13 0.8(7) . . . . ?
C15 C14 C13 C12 -0.6(7) . . . . ?
C14 C13 C12 C11 -0.1(6) . . . . ?
N6 C26 C27 C28 0.3(7) . . . . ?
P2 C26 C27 C28 178.2(3) . . . . ?
C26 C27 C28 C29 0.3(7) . . . . ?
C27 C28 C29 C30 -0.6(7) . . . . ?
C28 C29 C30 N6 0.3(7) . . . . ?
N5 C21 C22 C23 0.1(6) . . . . ?
P2 C21 C22 C23 -177.6(3) . . . . ?
C21 C22 C23 C24 -1.0(6) . . . . ?
C22 C23 C24 C25 0.6(6) . . . . ?
C23 C24 C25 N5 0.5(7) . . . . ?
N4 C16 C17 C18 0.3(6) . . . . ?
P2 C16 C17 C18 179.5(3) . . . . ?
C16 C17 C18 C19 0.4(6) . . . . ?
C17 C18 C19 C20 -0.3(6) . . . . ?
C18 C19 C20 N4 -0.4(7) . . . . ?
C5 N1 C1 C2 -0.8(6) . . . . ?
Cu1 N1 C1 C2 178.0(3) . . . . ?
C5 N1 C1 P1 178.6(3) . . . . ?
Cu1 N1 C1 P1 -2.7(4) . . . . ?
C3 C2 C1 N1 0.9(6) . . . . ?
C3 C2 C1 P1 -178.4(3) . . . . ?
C10 N2 C6 C7 0.7(6) . . . . ?
Cu1 N2 C6 C7 -177.6(3) . . . . ?
C10 N2 C6 P1 -176.7(3) . . . . ?
Cu1 N2 C6 P1 5.0(4) . . . . ?
C8 C7 C6 N2 -0.9(7) . . . . ?
C8 C7 C6 P1 176.5(3) . . . . ?
C15 N3 C11 C12 -0.6(6) . . . . ?
Cu1 N3 C11 C12 177.8(3) . . . . ?
C15 N3 C11 P1 179.8(3) . . . . ?
Cu1 N3 C11 P1 -1.8(4) . . . . ?
C13 C12 C11 N3 0.7(6) . . . . ?
C13 C12 C11 P1 -179.7(3) . . . . ?
C29 C30 N6 C26 0.3(6) . . . . ?
C29 C30 N6 Cu2 -177.9(3) . . . . ?
C27 C26 N6 C30 -0.6(6) . . . . ?
P2 C26 N6 C30 -178.5(3) . . . . ?
C27 C26 N6 Cu2 177.8(3) . . . . ?
P2 C26 N6 Cu2 -0.1(4) . . . . ?
C24 C25 N5 C21 -1.3(6) . . . . ?
C24 C25 N5 Cu2 173.8(3) . . . . ?
C22 C21 N5 C25 1.0(6) . . . . ?
P2 C21 N5 C25 178.7(3) . . . . ?
C22 C21 N5 Cu2 -174.6(3) . . . . ?
P2 C21 N5 Cu2 3.1(4) . . . . ?
C19 C20 N4 C16 1.0(6) . . . . ?
C19 C20 N4 Cu2 179.0(3) . . . . ?
C17 C16 N4 C20 -1.0(6) . . . . ?
P2 C16 N4 C20 179.8(3) . . . . ?
C17 C16 N4 Cu2 -179.2(3) . . . . ?
P2 C16 N4 Cu2 1.6(4) . . . . ?
N1 C1 P1 O1 -178.6(3) . . . . ?
C2 C1 P1 O1 0.8(4) . . . . ?
N1 C1 P1 C11 -54.3(4) . . . . ?
C2 C1 P1 C11 125.1(4) . . . . ?
N1 C1 P1 C6 57.1(4) . . . . ?
C2 C1 P1 C6 -123.5(4) . . . . ?
N3 C11 P1 O1 -177.9(3) . . . . ?
C12 C11 P1 O1 2.5(4) . . . . ?
N3 C11 P1 C1 57.6(3) . . . . ?
C12 C11 P1 C1 -122.0(3) . . . . ?
N3 C11 P1 C6 -54.3(3) . . . . ?
C12 C11 P1 C6 126.1(3) . . . . ?
N2 C6 P1 O1 176.1(3) . . . . ?
C7 C6 P1 O1 -1.4(4) . . . . ?
N2 C6 P1 C1 -59.0(4) . . . . ?
C7 C6 P1 C1 123.5(4) . . . . ?
N2 C6 P1 C11 52.2(4) . . . . ?
C7 C6 P1 C11 -125.3(4) . . . . ?
N4 C16 P2 O2 -180.0(3) . . . . ?
C17 C16 P2 O2 0.8(4) . . . . ?
N4 C16 P2 C21 54.5(3) . . . . ?
C17 C16 P2 C21 -124.8(3) . . . . ?
N4 C16 P2 C26 -57.6(4) . . . . ?
C17 C16 P2 C26 123.1(3) . . . . ?
N5 C21 P2 O2 176.5(3) . . . . ?
C22 C21 P2 O2 -5.6(4) . . . . ?
N5 C21 P2 C16 -57.9(3) . . . . ?
C22 C21 P2 C16 120.0(3) . . . . ?
N5 C21 P2 C26 52.1(3) . . . . ?
C22 C21 P2 C26 -130.1(3) . . . . ?
N6 C26 P2 O2 -179.5(3) . . . . ?
C27 C26 P2 O2 2.5(4) . . . . ?
N6 C26 P2 C16 57.4(4) . . . . ?
C27 C26 P2 C16 -120.6(4) . . . . ?
N6 C26 P2 C21 -54.2(4) . . . . ?
C27 C26 P2 C21 127.8(4) . . . . ?

_refine_diff_density_max         0.804
_refine_diff_density_min         -0.768
_refine_diff_density_rms         0.103

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
#######################################################################
#
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#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
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#  to carry out CIF format checking respectively.
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data_tgv54

_database_code_depnum_ccdc_archive 'CCDC 1021440'
_audit_contact_author            'Joerg Sundermeyer'
_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
'Chloro tris(2-pyridyl)phosphinesulfide copper(I)'
_chemical_name_common            'C4; CuCltpyps'
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 Cl Cu N3 P S, 1.5(C2 H3 N)'
_chemical_formula_sum            'C18 H16.50 Cl Cu N4.50 P S'
_chemical_formula_weight         457.88

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

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

_cell_length_a                   15.0776(12)
_cell_length_b                   30.280(2)
_cell_length_c                   8.6832(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3964.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4472
_cell_measurement_theta_min      1.51
_cell_measurement_theta_max      25.94

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_F_000             1864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.434
_shelx_estimated_absorpt_T_min   0.716
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8576
_exptl_absorpt_correction_T_max  0.8917
_exptl_absorpt_process_details   
;
R. H. Blessing, Acta Cryst. A 1995, 51, 33-38.
;

_exptl_special_details           ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   
;
sealed X-ray tube, 12 x 0.4 mm long-fine focus
;
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            13790
_diffrn_reflns_av_unetI/netI     0.1493
_diffrn_reflns_av_R_equivalents  0.1005
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.509
_diffrn_reflns_theta_max         26.721
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4187
_reflns_number_gt                1823
_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       
;
Stoe & Cie: X-AREA v1.56, Stoe & Cie GmbH, Darmstadt, Germany, 2011
;
_computing_cell_refinement       
;
Stoe & Cie: X-AREA v1.56, Stoe & Cie GmbH, Darmstadt, Germany, 2011
;
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    
;
SIR97 (A. Altomare, M. C. Burla, M. Camalli, G. Cascarano, C. Giacovazzo, 
A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, 
J. Appl. Crystallogr. 1999, 32, 115-119.)
;
_computing_structure_refinement  
;
SHELXL-2014 (G. Sheldrick, Acta Cryst. A 2008, 64, 112-122)
;
_computing_molecular_graphics    
;
K. Brandenburg, H. Putz: 
Diamond - Crystal and Molecular Structure Visualization v3.2i, 
Crystal Impact GbR, Bonn, Germany, 2012
;
_computing_publication_material  
;
WinGX publication routines (L. Farrugia, 
J. Appl. Crystallogr. 1999, 32, 837-838.)
;
_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)+(0.0151P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4187
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1226
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.0703
_refine_ls_wR_factor_gt          0.0583
_refine_ls_goodness_of_fit_ref   0.715
_refine_ls_restrained_S_all      0.715
_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
C11 C 0.3975(3) 0.17795(14) 0.6956(5) 0.0288(11) Uani 1 1 d . . . . .
C12 C 0.3518(3) 0.21753(14) 0.6980(5) 0.0321(11) Uani 1 1 d . . . . .
H12 H 0.2980 0.2204 0.6421 0.039 Uiso 1 1 calc R U . . .
C13 C 0.3838(3) 0.25274(16) 0.7804(6) 0.0374(12) Uani 1 1 d . . . . .
H13 H 0.3528 0.2801 0.7819 0.045 Uiso 1 1 calc R U . . .
C14 C 0.4617(3) 0.24760(15) 0.8610(5) 0.0377(11) Uani 1 1 d . . . . .
H14 H 0.4851 0.2712 0.9207 0.045 Uiso 1 1 calc R U . . .
C15 C 0.5052(3) 0.20748(15) 0.8536(6) 0.0347(11) Uani 1 1 d . . . . .
H15 H 0.5597 0.2046 0.9073 0.042 Uiso 1 1 calc R U . . .
C6 C 0.4495(3) 0.12151(13) 0.4465(5) 0.0277(10) Uani 1 1 d . . . . .
C7 C 0.4381(3) 0.12299(13) 0.2896(5) 0.0322(12) Uani 1 1 d . . . . .
H7 H 0.3824 0.1309 0.2468 0.039 Uiso 1 1 calc R U . . .
C8 C 0.5093(3) 0.11269(15) 0.1943(5) 0.0383(12) Uani 1 1 d . . . . .
H8 H 0.5029 0.1133 0.0855 0.046 Uiso 1 1 calc R U . . .
C9 C 0.5891(3) 0.10162(13) 0.2605(6) 0.0375(11) Uani 1 1 d . . . . .
H9 H 0.6387 0.0943 0.1982 0.045 Uiso 1 1 calc R U . . .
C10 C 0.5959(3) 0.10135(14) 0.4183(5) 0.0344(11) Uani 1 1 d . . . . .
H10 H 0.6515 0.0939 0.4628 0.041 Uiso 1 1 calc R U . . .
C1 C 0.3528(3) 0.08257(13) 0.6988(5) 0.0299(11) Uani 1 1 d . . . . .
C2 C 0.2801(3) 0.05464(15) 0.6917(5) 0.0349(12) Uani 1 1 d . . . . .
H2 H 0.2310 0.0613 0.6271 0.042 Uiso 1 1 calc R U . . .
C3 C 0.2809(3) 0.01691(14) 0.7811(6) 0.0373(13) Uani 1 1 d . . . . .
H3 H 0.2324 -0.0031 0.7778 0.045 Uiso 1 1 calc R U . . .
C4 C 0.3522(3) 0.00860(15) 0.8748(6) 0.0391(12) Uani 1 1 d . . . . .
H4 H 0.3532 -0.0169 0.9383 0.047 Uiso 1 1 calc R U . . .
C5 C 0.4221(3) 0.03760(15) 0.8756(6) 0.0368(12) Uani 1 1 d . . . . .
H5 H 0.4712 0.0316 0.9410 0.044 Uiso 1 1 calc R U . . .
C16 C 0.7656(3) 0.17718(17) 0.6424(7) 0.0549(15) Uani 1 1 d . . . . .
H16A H 0.7412 0.1555 0.7149 0.082 Uiso 1 1 calc R U . . .
H16B H 0.8079 0.1963 0.6961 0.082 Uiso 1 1 calc R U . . .
H16C H 0.7959 0.1617 0.5584 0.082 Uiso 1 1 calc R U . . .
C17 C 0.6944(3) 0.20371(17) 0.5801(7) 0.0494(15) Uani 1 1 d . . . . .
N3 N 0.4751(2) 0.17237(11) 0.7751(4) 0.0308(9) Uani 1 1 d . . . . .
N2 N 0.5280(2) 0.11101(12) 0.5134(4) 0.0323(8) Uani 1 1 d . . . . .
N1 N 0.4241(2) 0.07435(12) 0.7872(4) 0.0321(10) Uani 1 1 d . . . . .
N4 N 0.6390(3) 0.22441(16) 0.5292(7) 0.0809(18) Uani 1 1 d . . . . .
P1 P 0.35761(7) 0.13241(4) 0.57840(14) 0.0290(3) Uani 1 1 d . . . . .
S1 S 0.24637(9) 0.14588(4) 0.47601(15) 0.0354(3) Uani 1 1 d . . . . .
Cl1 Cl 0.65983(7) 0.08787(4) 0.85940(14) 0.0360(3) Uani 1 1 d . . . . .
Cu1 Cu 0.53588(3) 0.11309(2) 0.75044(8) 0.03279(13) Uani 1 1 d . . . . .
C19 C -0.0114(13) -0.0066(8) 1.026(2) 0.078(4) Uani 0.5 1 d . . P A -1
N5 N -0.061(2) -0.0134(9) 1.099(4) 0.078(4) Uani 0.5 1 d . . P A -1
C18 C 0.066(2) 0.0010(11) 0.909(5) 0.078(4) Uani 0.5 1 d . . P A -1
H18A H 0.0474 0.0224 0.8303 0.117 Uiso 0.5 1 calc R U P A -1
H18B H 0.0816 -0.0270 0.8591 0.117 Uiso 0.5 1 calc R U P A -1
H18C H 0.1182 0.0126 0.9634 0.117 Uiso 0.5 1 calc R U P A -1


_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
C11 N3 1.369(5) . ?
C11 C12 1.382(6) . ?
C11 P1 1.817(4) . ?
C12 C13 1.371(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.376(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(6) . ?
C14 H14 0.9500 . ?
C15 N3 1.342(5) . ?
C15 H15 0.9500 . ?
C6 N2 1.357(5) . ?
C6 C7 1.374(5) . ?
C6 P1 1.827(4) . ?
C7 C8 1.391(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.375(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.374(6) . ?
C9 H9 0.9500 . ?
C10 N2 1.347(5) . ?
C10 H10 0.9500 . ?
C1 N1 1.344(5) . ?
C1 C2 1.386(5) . ?
C1 P1 1.837(4) . ?
C2 C3 1.381(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.372(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.372(6) . ?
C4 H4 0.9500 . ?
C5 N1 1.352(5) . ?
C5 H5 0.9500 . ?
C16 C17 1.445(7) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 N4 1.135(6) . ?
N3 Cu1 2.027(3) . ?
N2 Cu1 2.063(3) . ?
N1 Cu1 2.078(3) . ?
P1 S1 1.9416(17) . ?
Cl1 Cu1 2.2295(12) . ?
C19 N5 1.01(5) . ?
C19 C18 1.57(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
N3 C11 C12 121.7(4) . . ?
N3 C11 P1 118.1(3) . . ?
C12 C11 P1 120.1(3) . . ?
C13 C12 C11 120.5(4) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 118.5(4) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
C13 C14 C15 118.7(4) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
N3 C15 C14 124.1(4) . . ?
N3 C15 H15 118.0 . . ?
C14 C15 H15 118.0 . . ?
N2 C6 C7 122.7(4) . . ?
N2 C6 P1 115.9(3) . . ?
C7 C6 P1 121.4(3) . . ?
C6 C7 C8 119.1(4) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C9 C8 C7 118.8(4) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C10 C9 C8 118.9(4) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
N2 C10 C9 123.6(4) . . ?
N2 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
N1 C1 C2 123.0(4) . . ?
N1 C1 P1 116.5(3) . . ?
C2 C1 P1 120.5(3) . . ?
C3 C2 C1 118.2(4) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C4 C3 C2 119.5(4) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C5 C4 C3 119.2(4) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
N1 C5 C4 122.7(4) . . ?
N1 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N4 C17 C16 179.0(7) . . ?
C15 N3 C11 116.5(4) . . ?
C15 N3 Cu1 127.1(3) . . ?
C11 N3 Cu1 116.3(3) . . ?
C10 N2 C6 116.9(4) . . ?
C10 N2 Cu1 125.1(3) . . ?
C6 N2 Cu1 118.0(3) . . ?
C1 N1 C5 117.3(4) . . ?
C1 N1 Cu1 117.2(3) . . ?
C5 N1 Cu1 124.7(3) . . ?
C11 P1 C6 103.71(18) . . ?
C11 P1 C1 108.53(19) . . ?
C6 P1 C1 103.78(19) . . ?
C11 P1 S1 112.53(15) . . ?
C6 P1 S1 113.95(14) . . ?
C1 P1 S1 113.53(15) . . ?
N3 Cu1 N2 96.10(15) . . ?
N3 Cu1 N1 96.72(13) . . ?
N2 Cu1 N1 95.14(14) . . ?
N3 Cu1 Cl1 129.61(11) . . ?
N2 Cu1 Cl1 117.46(10) . . ?
N1 Cu1 Cl1 114.93(10) . . ?
N5 C19 C18 177(2) . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C19 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
N3 C11 C12 C13 0.3(6) . . . . ?
P1 C11 C12 C13 -176.9(3) . . . . ?
C11 C12 C13 C14 -0.4(7) . . . . ?
C12 C13 C14 C15 1.0(7) . . . . ?
C13 C14 C15 N3 -1.7(7) . . . . ?
N2 C6 C7 C8 1.0(7) . . . . ?
P1 C6 C7 C8 -177.4(3) . . . . ?
C6 C7 C8 C9 -0.4(6) . . . . ?
C7 C8 C9 C10 -0.4(7) . . . . ?
C8 C9 C10 N2 0.6(7) . . . . ?
N1 C1 C2 C3 0.7(6) . . . . ?
P1 C1 C2 C3 178.1(3) . . . . ?
C1 C2 C3 C4 0.9(7) . . . . ?
C2 C3 C4 C5 -1.1(7) . . . . ?
C3 C4 C5 N1 -0.2(7) . . . . ?
C14 C15 N3 C11 1.6(7) . . . . ?
C14 C15 N3 Cu1 177.5(4) . . . . ?
C12 C11 N3 C15 -0.9(6) . . . . ?
P1 C11 N3 C15 176.4(3) . . . . ?
C12 C11 N3 Cu1 -177.3(3) . . . . ?
P1 C11 N3 Cu1 0.0(4) . . . . ?
C9 C10 N2 C6 -0.1(6) . . . . ?
C9 C10 N2 Cu1 -177.9(3) . . . . ?
C7 C6 N2 C10 -0.8(6) . . . . ?
P1 C6 N2 C10 177.8(3) . . . . ?
C7 C6 N2 Cu1 177.2(3) . . . . ?
P1 C6 N2 Cu1 -4.3(4) . . . . ?
C2 C1 N1 C5 -2.0(6) . . . . ?
P1 C1 N1 C5 -179.4(3) . . . . ?
C2 C1 N1 Cu1 168.3(3) . . . . ?
P1 C1 N1 Cu1 -9.2(4) . . . . ?
C4 C5 N1 C1 1.7(7) . . . . ?
C4 C5 N1 Cu1 -167.7(3) . . . . ?
N3 C11 P1 C6 -57.0(4) . . . . ?
C12 C11 P1 C6 120.3(4) . . . . ?
N3 C11 P1 C1 52.9(4) . . . . ?
C12 C11 P1 C1 -129.8(3) . . . . ?
N3 C11 P1 S1 179.4(3) . . . . ?
C12 C11 P1 S1 -3.3(4) . . . . ?
N2 C6 P1 C11 58.7(4) . . . . ?
C7 C6 P1 C11 -122.8(4) . . . . ?
N2 C6 P1 C1 -54.7(4) . . . . ?
C7 C6 P1 C1 123.9(4) . . . . ?
N2 C6 P1 S1 -178.6(3) . . . . ?
C7 C6 P1 S1 -0.1(4) . . . . ?
N1 C1 P1 C11 -46.4(4) . . . . ?
C2 C1 P1 C11 136.1(3) . . . . ?
N1 C1 P1 C6 63.5(3) . . . . ?
C2 C1 P1 C6 -114.0(4) . . . . ?
N1 C1 P1 S1 -172.3(3) . . . . ?
C2 C1 P1 S1 10.2(4) . . . . ?

_refine_diff_density_max         0.467
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.077

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_tgv55

_database_code_depnum_ccdc_archive 'CCDC 1021441'
_audit_contact_author            'Joerg Sundermeyer'
_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
Bromo tris(2-pyridyl)phosphinesulfide copper(I)
;
_chemical_name_common            'C5, CuBrtpyps'
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H19.5 Br1 Cu1 N5.5 P1 S1'
_chemical_formula_sum            'C20 H19.50 Br Cu N5.50 P S'
_chemical_formula_weight         543.39

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/a'
_space_group_name_Hall           '-P 2yab'

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

_cell_length_a                   8.5838(3)
_cell_length_b                   15.2046(7)
_cell_length_c                   17.8716(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.386(3)
_cell_angle_gamma                90
_cell_volume                     2269.11(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11724
_cell_measurement_theta_min      1.775
_cell_measurement_theta_max      27.225

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_F_000             1092
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.904
_shelx_estimated_absorpt_T_min   0.594
_shelx_estimated_absorpt_T_max   0.868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6731
_exptl_absorpt_correction_T_max  0.7337
_exptl_absorpt_process_details   
; 
R. H. Blessing, Acta Cryst. A 1995, 51, 33-38.
;

_exptl_special_details           ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   
;
sealed X-ray tube, 12 x 0.4 mm long-fine focus 
;
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            17036
_diffrn_reflns_av_unetI/netI     0.0696
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.779
_diffrn_reflns_theta_max         26.713
_diffrn_reflns_theta_full        25.000
_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             4804
_reflns_number_gt                3562
_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       
;
Stoe & Cie: X-AREA v1.56, Stoe & Cie GmbH, Darmstadt, Germany, 2011
;
_computing_cell_refinement       
;
Stoe & Cie: X-AREA v1.56, Stoe & Cie GmbH, Darmstadt, Germany, 2011
;
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    
;
SIR97 (A. Altomare, M. C. Burla, M. Camalli, G. Cascarano, C. Giacovazzo, 
A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, 
J. Appl. Crystallogr. 1999, 32, 115-119.)
;
_computing_structure_refinement  
;
SHELXL-2014 (G. Sheldrick, Acta Cryst. A 2008, 64, 112-122)
;
_computing_molecular_graphics    
;
K. Brandenburg, H. Putz: 
Diamond - Crystal and Molecular Structure Visualization v3.2i, 
Crystal Impact GbR, Bonn, Germany, 2012
;
_computing_publication_material  
;
WinGX publication routines (L. Farrugia, 
J. Appl. Crystallogr. 1999, 32, 837-838.)
;

_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)+(0.0584P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4804
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1196
_refine_ls_wR_factor_gt          0.1145
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_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
C7 C 0.7545(7) 0.7765(3) 0.3957(3) 0.0206(11) Uani 1 1 d . . . . .
H7 H 0.8064 0.7269 0.3800 0.025 Uiso 1 1 calc R U . . .
N3 N 0.9010(5) 1.0242(3) 0.3039(2) 0.0180(9) Uani 1 1 d . . . . .
N1 N 0.5712(5) 0.9804(3) 0.2039(2) 0.0183(9) Uani 1 1 d . . . . .
C9 C 0.6257(7) 0.8477(4) 0.4848(3) 0.0287(13) Uani 1 1 d . . . . .
H9 H 0.5880 0.8479 0.5308 0.034 Uiso 1 1 calc R U . . .
C4 C 0.4004(7) 0.9776(4) 0.0773(3) 0.0271(12) Uani 1 1 d . . . . .
H4 H 0.3157 1.0035 0.0401 0.033 Uiso 1 1 calc R U . . .
C5 C 0.4542(7) 1.0160(4) 0.1494(3) 0.0250(12) Uani 1 1 d . . . . .
H5 H 0.4063 1.0694 0.1604 0.030 Uiso 1 1 calc R U . . .
C3 C 0.4728(7) 0.9011(4) 0.0612(3) 0.0252(12) Uani 1 1 d . . . . .
H3 H 0.4398 0.8743 0.0121 0.030 Uiso 1 1 calc R U . . .
C14 C 1.1680(7) 1.0796(4) 0.3172(3) 0.0270(12) Uani 1 1 d . . . . .
H14 H 1.2410 1.1273 0.3289 0.032 Uiso 1 1 calc R U . . .
C8 C 0.7027(8) 0.7751(4) 0.4645(3) 0.0303(13) Uani 1 1 d . . . . .
H8 H 0.7205 0.7247 0.4968 0.036 Uiso 1 1 calc R U . . .
C19 C 0.7910(7) 0.2531(4) 0.0998(3) 0.0277(13) Uani 1 1 d . . . . .
C16 C 0.0231(8) 0.8729(4) 0.0738(3) 0.0316(13) Uani 1 1 d . . . . .
H16A H 0.1036 0.8554 0.1197 0.047 Uiso 1 1 calc R U . . .
H16B H 0.0716 0.8734 0.0292 0.047 Uiso 1 1 calc R U . . .
H16C H -0.0661 0.8311 0.0648 0.047 Uiso 1 1 calc R U . . .
C6 C 0.7283(6) 0.8520(3) 0.3511(3) 0.0164(10) Uani 1 1 d . . . . .
C15 C 1.0087(7) 1.0896(3) 0.3202(3) 0.0236(11) Uani 1 1 d . . . . .
H15 H 0.9743 1.1453 0.3344 0.028 Uiso 1 1 calc R U . . .
C13 C 1.2174(7) 0.9984(4) 0.2967(3) 0.0243(11) Uani 1 1 d . . . . .
H13 H 1.3255 0.9896 0.2939 0.029 Uiso 1 1 calc R U . . .
C1 C 0.6395(6) 0.9057(3) 0.1878(3) 0.0155(10) Uani 1 1 d . . . . .
N5 N 0.8224(8) 0.2796(4) 0.0460(3) 0.0431(14) Uani 1 1 d . . . . .
C17 C -0.0355(8) 0.9601(4) 0.0850(3) 0.0336(14) Uani 1 1 d . . . . .
C11 C 0.9518(6) 0.9452(3) 0.2840(3) 0.0172(10) Uani 1 1 d . . . . .
N4 N -0.0817(9) 1.0289(4) 0.0952(3) 0.0511(16) Uani 1 1 d . . . . .
C18 C 0.7523(9) 0.2182(5) 0.1690(3) 0.0437(17) Uani 1 1 d . . . . .
H18A H 0.7769 0.1552 0.1732 0.066 Uiso 1 1 calc R U . . .
H18B H 0.6381 0.2270 0.1664 0.066 Uiso 1 1 calc R U . . .
H18C H 0.8158 0.2489 0.2141 0.066 Uiso 1 1 calc R U . . .
C10 C 0.6042(7) 0.9206(4) 0.4369(3) 0.0268(12) Uani 1 1 d . . . . .
H10 H 0.5500 0.9703 0.4508 0.032 Uiso 1 1 calc R U . . .
C2 C 0.5933(6) 0.8639(3) 0.1169(3) 0.0198(11) Uani 1 1 d . . . . .
H2 H 0.6437 0.8109 0.1070 0.024 Uiso 1 1 calc R U . . .
C12 C 1.1083(6) 0.9300(4) 0.2805(3) 0.0192(11) Uani 1 1 d . . . . .
H12 H 1.1408 0.8735 0.2671 0.023 Uiso 1 1 calc R U . . .
N2 N 0.6567(5) 0.9240(3) 0.3716(2) 0.0203(9) Uani 1 1 d . . . . .
S1 S 0.88222(16) 0.74789(8) 0.23306(7) 0.0195(3) Uani 1 1 d . . . . .
P1 P 0.80079(15) 0.85865(8) 0.26284(7) 0.0136(3) Uani 1 1 d . . . . .
Cu1 Cu 0.66583(8) 1.03599(4) 0.30868(4) 0.02014(17) Uani 1 1 d . . . . .
Br1 Br 0.57916(6) 1.17258(3) 0.34301(3) 0.01771(14) Uani 1 1 d . . . . .
N6 N 0.591(3) 0.5653(16) 0.4694(9) 0.053(5) Uani 0.5 1 d . . P A -1
C21 C 0.5250(18) 0.5103(10) 0.4846(8) 0.033(3) Uani 0.5 1 d . . P A -1
C20 C 0.430(3) 0.4324(18) 0.5000(11) 0.041(5) Uani 0.5 1 d . . P A -1
H20A H 0.3432 0.4209 0.4548 0.061 Uiso 0.5 1 calc R U P A -1
H20B H 0.3848 0.4446 0.5444 0.061 Uiso 0.5 1 calc R U P A -1
H20C H 0.5002 0.3808 0.5107 0.061 Uiso 0.5 1 calc R U P A -1


_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
C7 C6 1.386(7) . ?
C7 C8 1.402(7) . ?
C7 H7 0.9500 . ?
N3 C15 1.344(7) . ?
N3 C11 1.353(6) . ?
N3 Cu1 2.048(4) . ?
N1 C1 1.339(6) . ?
N1 C5 1.341(7) . ?
N1 Cu1 2.043(4) . ?
C9 C8 1.378(9) . ?
C9 C10 1.386(8) . ?
C9 H9 0.9500 . ?
C4 C3 1.380(8) . ?
C4 C5 1.393(8) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C3 C2 1.380(7) . ?
C3 H3 0.9500 . ?
C14 C13 1.381(8) . ?
C14 C15 1.389(8) . ?
C14 H14 0.9500 . ?
C8 H8 0.9500 . ?
C19 N5 1.132(7) . ?
C19 C18 1.453(8) . ?
C16 C17 1.448(9) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C6 N2 1.348(6) . ?
C6 P1 1.827(5) . ?
C15 H15 0.9500 . ?
C13 C12 1.385(8) . ?
C13 H13 0.9500 . ?
C1 C2 1.391(7) . ?
C1 P1 1.835(5) . ?
C17 N4 1.149(8) . ?
C11 C12 1.379(7) . ?
C11 P1 1.825(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C10 N2 1.346(6) . ?
C10 H10 0.9500 . ?
C2 H2 0.9500 . ?
C12 H12 0.9500 . ?
N2 Cu1 2.052(4) . ?
S1 P1 1.9443(17) . ?
Cu1 Br1 2.3354(8) . ?
N6 C21 1.08(3) . ?
C21 C20 1.50(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C6 C7 C8 118.4(5) . . ?
C6 C7 H7 120.8 . . ?
C8 C7 H7 120.8 . . ?
C15 N3 C11 117.8(4) . . ?
C15 N3 Cu1 124.1(3) . . ?
C11 N3 Cu1 118.0(3) . . ?
C1 N1 C5 118.5(4) . . ?
C1 N1 Cu1 116.6(3) . . ?
C5 N1 Cu1 124.8(4) . . ?
C8 C9 C10 118.8(5) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C3 C4 C5 118.5(5) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 122.3(5) . . ?
N1 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
C4 C3 C2 119.6(5) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C13 C14 C15 118.3(5) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 H14 120.9 . . ?
C9 C8 C7 119.2(5) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
N5 C19 C18 179.3(8) . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C6 C7 122.7(4) . . ?
N2 C6 P1 117.2(4) . . ?
C7 C6 P1 120.0(4) . . ?
N3 C15 C14 123.0(5) . . ?
N3 C15 H15 118.5 . . ?
C14 C15 H15 118.5 . . ?
C14 C13 C12 119.5(5) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
N1 C1 C2 122.5(5) . . ?
N1 C1 P1 117.8(4) . . ?
C2 C1 P1 119.7(4) . . ?
N4 C17 C16 178.8(6) . . ?
N3 C11 C12 122.6(5) . . ?
N3 C11 P1 115.9(4) . . ?
C12 C11 P1 121.5(4) . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C19 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C10 C9 122.9(5) . . ?
N2 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?
C3 C2 C1 118.5(5) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C11 C12 C13 118.8(5) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C10 N2 C6 118.0(5) . . ?
C10 N2 Cu1 124.8(4) . . ?
C6 N2 Cu1 116.6(3) . . ?
C11 P1 C6 103.2(2) . . ?
C11 P1 C1 104.5(2) . . ?
C6 P1 C1 107.6(2) . . ?
C11 P1 S1 113.47(17) . . ?
C6 P1 S1 113.82(17) . . ?
C1 P1 S1 113.32(17) . . ?
N1 Cu1 N3 96.43(17) . . ?
N1 Cu1 N2 95.79(16) . . ?
N3 Cu1 N2 96.51(17) . . ?
N1 Cu1 Br1 121.69(12) . . ?
N3 Cu1 Br1 117.78(12) . . ?
N2 Cu1 Br1 122.62(12) . . ?
N6 C21 C20 176.0(18) . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C1 N1 C5 C4 0.8(8) . . . . ?
Cu1 N1 C5 C4 176.3(4) . . . . ?
C3 C4 C5 N1 -1.4(8) . . . . ?
C5 C4 C3 C2 1.3(8) . . . . ?
C10 C9 C8 C7 -1.0(9) . . . . ?
C6 C7 C8 C9 1.0(8) . . . . ?
C8 C7 C6 N2 0.7(8) . . . . ?
C8 C7 C6 P1 177.5(4) . . . . ?
C11 N3 C15 C14 0.2(7) . . . . ?
Cu1 N3 C15 C14 179.4(4) . . . . ?
C13 C14 C15 N3 -0.2(8) . . . . ?
C15 C14 C13 C12 -0.4(8) . . . . ?
C5 N1 C1 C2 -0.2(7) . . . . ?
Cu1 N1 C1 C2 -176.0(4) . . . . ?
C5 N1 C1 P1 179.4(4) . . . . ?
Cu1 N1 C1 P1 3.5(5) . . . . ?
C15 N3 C11 C12 0.4(7) . . . . ?
Cu1 N3 C11 C12 -178.8(4) . . . . ?
C15 N3 C11 P1 179.8(4) . . . . ?
Cu1 N3 C11 P1 0.6(5) . . . . ?
C8 C9 C10 N2 -0.7(9) . . . . ?
C4 C3 C2 C1 -0.7(8) . . . . ?
N1 C1 C2 C3 0.2(7) . . . . ?
P1 C1 C2 C3 -179.4(4) . . . . ?
N3 C11 C12 C13 -1.0(7) . . . . ?
P1 C11 C12 C13 179.6(4) . . . . ?
C14 C13 C12 C11 1.0(8) . . . . ?
C9 C10 N2 C6 2.3(8) . . . . ?
C9 C10 N2 Cu1 -168.3(4) . . . . ?
C7 C6 N2 C10 -2.3(8) . . . . ?
P1 C6 N2 C10 -179.2(4) . . . . ?
C7 C6 N2 Cu1 169.1(4) . . . . ?
P1 C6 N2 Cu1 -7.9(5) . . . . ?
N3 C11 P1 C6 -57.3(4) . . . . ?
C12 C11 P1 C6 122.0(4) . . . . ?
N3 C11 P1 C1 55.1(4) . . . . ?
C12 C11 P1 C1 -125.5(4) . . . . ?
N3 C11 P1 S1 179.0(3) . . . . ?
C12 C11 P1 S1 -1.6(5) . . . . ?
N2 C6 P1 C11 62.4(4) . . . . ?
C7 C6 P1 C11 -114.6(4) . . . . ?
N2 C6 P1 C1 -47.7(4) . . . . ?
C7 C6 P1 C1 135.3(4) . . . . ?
N2 C6 P1 S1 -174.1(3) . . . . ?
C7 C6 P1 S1 8.9(5) . . . . ?
N1 C1 P1 C11 -58.5(4) . . . . ?
C2 C1 P1 C11 121.0(4) . . . . ?
N1 C1 P1 C6 50.7(4) . . . . ?
C2 C1 P1 C6 -129.7(4) . . . . ?
N1 C1 P1 S1 177.5(3) . . . . ?
C2 C1 P1 S1 -2.9(4) . . . . ?

_refine_diff_density_max         0.763
_refine_diff_density_min         -0.840
_refine_diff_density_rms         0.117

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_TGV40

_database_code_depnum_ccdc_archive 'CCDC 1021442'
_audit_contact_author            'Joerg Sundermeyer'

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
Iodo tris(2-pyridyl)phosphinesulfide copper(I)
;
_chemical_name_common            'C6, CuItpyps'
_chemical_melting_point          ?
_chemical_formula_moiety         '3(C15 H12 Cu I N3 P S), C2 H3 N'
_chemical_formula_sum            'C47 H39 Cu3 I3 N10 P3 S3'
_chemical_formula_weight         1504.35

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c 21 b'
_space_group_name_Hall           'P -2bc -2c'

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

_cell_length_a                   13.2413(5)
_cell_length_b                   15.7217(6)
_cell_length_c                   25.7987(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5370.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11285
_cell_measurement_theta_min      1.535
_cell_measurement_theta_max      27.07

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.860
_exptl_crystal_F_000             2920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    3.152
_shelx_estimated_absorpt_T_min   0.442
_shelx_estimated_absorpt_T_max   0.601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4067
_exptl_absorpt_correction_T_max  0.4993
_exptl_absorpt_process_details   
; 
R. H. Blessing, Acta Cryst. A 1995, 51, 33-38.
;

_exptl_special_details           ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   
;
sealed X-ray tube, 12 x 0.4 mm long-fine focus
;
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            18930
_diffrn_reflns_av_unetI/netI     0.1120
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.729
_diffrn_reflns_theta_max         26.739
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_point_group_measured_fraction_full 0.910
_reflns_number_total             10265
_reflns_number_gt                6869
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_max     0.798
_reflns_Friedel_fraction_full    0.814

_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       
;
Stoe & Cie: X-AREA v1.56, Stoe & Cie GmbH, Darmstadt, Germany, 2011
;
_computing_cell_refinement       
;
Stoe & Cie: X-AREA v1.56, Stoe & Cie GmbH, Darmstadt, Germany, 2011
;
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    
;
SIR97 (A. Altomare, M. C. Burla, M. Camalli, G. Cascarano, C. Giacovazzo, 
A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, 
J. Appl. Crystallogr. 1999, 32, 115-119.)
;
_computing_structure_refinement  
;
SHELXL-2014 (G. Sheldrick, Acta Cryst. A 2008, 64, 112-122)
;
_computing_molecular_graphics    
;
K. Brandenburg, H. Putz: 
Diamond - Crystal and Molecular Structure Visualization v3.2i, 
Crystal Impact GbR, Bonn, Germany, 2012
;
_computing_publication_material  
;
WinGX publication routines (L. Farrugia, 
J. Appl. Crystallogr. 1999, 32, 837-838.)
;

_refine_special_details          
; 
In contrast to the other structures presented in this article, 
the cell_formula_units_Z does not correspond to the number of 
complex molecules per cell, but to the number asymmetric untis 
per cell. This was done to avoid rounding errors, due to the 
odd number of molecules per asymmetric unit, which lead to 
artificial checkCIF/PLATON errors.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0354P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Classical Flack method preferred over Parsons because s.u. lower. 
;
_refine_ls_abs_structure_Flack   -0.01(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         10265
_refine_ls_number_parameters     623
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0822
_refine_ls_wR_factor_gt          0.0796
_refine_ls_goodness_of_fit_ref   0.747
_refine_ls_restrained_S_all      0.747
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2648(8) 0.6779(8) 0.8708(5) 0.023(3) Uani 1 1 d . . . . .
C2 C 0.2044(9) 0.7258(8) 0.9005(4) 0.027(3) Uani 1 1 d . . . . .
H2 H 0.1332 0.7229 0.8965 0.032 Uiso 1 1 calc R U . . .
C3 C 0.2467(10) 0.7801(8) 0.9376(4) 0.030(3) Uani 1 1 d . . . . .
H3 H 0.2054 0.8150 0.9590 0.036 Uiso 1 1 calc R U . . .
C4 C 0.3505(10) 0.7813(8) 0.9419(5) 0.031(3) Uani 1 1 d . . . . .
H4 H 0.3825 0.8170 0.9667 0.038 Uiso 1 1 calc R U . . .
C5 C 0.4073(9) 0.7298(9) 0.9097(5) 0.031(3) Uani 1 1 d . . . . .
H5 H 0.4788 0.7316 0.9125 0.038 Uiso 1 1 calc R U . . .
C11 C 0.2647(9) 0.6195(8) 0.7617(4) 0.026(3) Uani 1 1 d . . . . .
C12 C 0.2020(9) 0.6240(8) 0.7193(4) 0.026(3) Uani 1 1 d . . . . .
H12 H 0.1308 0.6198 0.7231 0.031 Uiso 1 1 calc R U . . .
C13 C 0.2458(11) 0.6348(8) 0.6705(5) 0.035(3) Uani 1 1 d . . . . .
H13 H 0.2050 0.6372 0.6402 0.043 Uiso 1 1 calc R U . . .
C14 C 0.3486(11) 0.6418(8) 0.6670(4) 0.035(3) Uani 1 1 d . . . . .
H14 H 0.3806 0.6489 0.6344 0.042 Uiso 1 1 calc R U . . .
C15 C 0.4041(10) 0.6383(8) 0.7114(4) 0.028(3) Uani 1 1 d . . . . .
H15 H 0.4752 0.6447 0.7084 0.034 Uiso 1 1 calc R U . . .
C6 C 0.2650(9) 0.4988(7) 0.8460(4) 0.020(3) Uani 1 1 d . . . . .
C7 C 0.2045(9) 0.4328(8) 0.8633(4) 0.028(3) Uani 1 1 d . . . . .
H7 H 0.1331 0.4387 0.8637 0.033 Uiso 1 1 calc R U . . .
C8 C 0.2494(10) 0.3583(8) 0.8801(4) 0.029(3) Uani 1 1 d . . . . .
H8 H 0.2094 0.3125 0.8926 0.034 Uiso 1 1 calc R U . . .
C9 C 0.3517(9) 0.3518(8) 0.8785(4) 0.029(3) Uani 1 1 d . . . . .
H9 H 0.3840 0.3014 0.8902 0.035 Uiso 1 1 calc R U . . .
C10 C 0.4091(9) 0.4195(9) 0.8594(4) 0.026(3) Uani 1 1 d . . . . .
H10 H 0.4803 0.4132 0.8570 0.032 Uiso 1 1 calc R U . . .
C16 C 0.2463(9) 0.4916(8) 0.0322(4) 0.024(3) Uani 1 1 d . . . . .
C17 C 0.1734(9) 0.4644(8) -0.0025(4) 0.025(3) Uani 1 1 d . . . . .
H17 H 0.1740 0.4079 -0.0155 0.030 Uiso 1 1 calc R U . . .
C18 C 0.1001(9) 0.5211(9) -0.0175(4) 0.029(3) Uani 1 1 d . . . . .
H18 H 0.0485 0.5042 -0.0409 0.034 Uiso 1 1 calc R U . . .
C19 C 0.1024(8) 0.6040(10) 0.0021(4) 0.029(3) Uani 1 1 d . . . . .
H19 H 0.0533 0.6446 -0.0082 0.035 Uiso 1 1 calc R U . . .
C20 C 0.1777(8) 0.6255(8) 0.0367(4) 0.026(3) Uani 1 1 d . . . . .
H20 H 0.1784 0.6813 0.0508 0.032 Uiso 1 1 calc R U . . .
C26 C 0.4586(8) 0.4836(7) 0.0225(4) 0.019(2) Uani 1 1 d . . . . .
C27 C 0.5118(8) 0.4519(8) -0.0194(4) 0.025(3) Uani 1 1 d . . . . .
H27 H 0.5015 0.3953 -0.0311 0.030 Uiso 1 1 calc R U . . .
C28 C 0.5797(9) 0.5044(8) -0.0437(4) 0.025(3) Uani 1 1 d . . . . .
H28 H 0.6182 0.4840 -0.0722 0.030 Uiso 1 1 calc R U . . .
C29 C 0.5921(8) 0.5871(8) -0.0268(4) 0.026(3) Uani 1 1 d . . . . .
H29 H 0.6364 0.6251 -0.0442 0.032 Uiso 1 1 calc R U . . .
C30 C 0.5383(8) 0.6128(9) 0.0161(4) 0.026(3) Uani 1 1 d . . . . .
H30 H 0.5494 0.6686 0.0291 0.031 Uiso 1 1 calc R U . . .
C21 C 0.3616(8) 0.4225(7) 0.1195(4) 0.019(2) Uani 1 1 d . . . . .
C22 C 0.3585(9) 0.3454(8) 0.1464(4) 0.024(3) Uani 1 1 d . . . . .
H22 H 0.3540 0.2926 0.1286 0.029 Uiso 1 1 calc R U . . .
C23 C 0.3622(9) 0.3488(8) 0.1998(4) 0.027(3) Uani 1 1 d . . . . .
H23 H 0.3589 0.2976 0.2193 0.033 Uiso 1 1 calc R U . . .
C24 C 0.3708(9) 0.4263(8) 0.2251(4) 0.028(3) Uani 1 1 d . . . . .
H24 H 0.3741 0.4291 0.2619 0.034 Uiso 1 1 calc R U . . .
C25 C 0.3745(8) 0.4995(8) 0.1952(4) 0.023(3) Uani 1 1 d . . . . .
H25 H 0.3800 0.5527 0.2125 0.028 Uiso 1 1 calc R U . . .
C36 C 1.0498(9) 0.4970(8) 0.1902(4) 0.024(3) Uani 1 1 d . . . . .
C37 C 1.1223(9) 0.5359(9) 0.2218(4) 0.029(3) Uani 1 1 d . . . . .
H37 H 1.1498 0.5067 0.2508 0.034 Uiso 1 1 calc R U . . .
C38 C 1.1526(8) 0.6170(9) 0.2103(4) 0.031(3) Uani 1 1 d . . . . .
H38 H 1.2019 0.6448 0.2310 0.037 Uiso 1 1 calc R U . . .
C39 C 1.1105(8) 0.6580(8) 0.1678(4) 0.027(3) Uani 1 1 d . . . . .
H39 H 1.1314 0.7138 0.1587 0.032 Uiso 1 1 calc R U . . .
C40 C 1.0387(8) 0.6170(8) 0.1397(4) 0.023(3) Uani 1 1 d . . . . .
H40 H 1.0085 0.6465 0.1115 0.027 Uiso 1 1 calc R U . . .
C31 C 0.8728(10) 0.3855(8) 0.2017(4) 0.029(3) Uani 1 1 d . . . . .
C32 C 0.8218(11) 0.3458(9) 0.2421(5) 0.039(3) Uani 1 1 d . . . . .
H32 H 0.8572 0.3202 0.2701 0.046 Uiso 1 1 calc R U . . .
C33 C 0.7168(11) 0.3448(9) 0.2399(4) 0.038(4) Uani 1 1 d . . . . .
H33 H 0.6794 0.3184 0.2669 0.046 Uiso 1 1 calc R U . . .
C34 C 0.6671(11) 0.3816(9) 0.1993(5) 0.043(4) Uani 1 1 d . . . . .
H34 H 0.5954 0.3813 0.1978 0.051 Uiso 1 1 calc R U . . .
C35 C 0.7236(9) 0.4194(8) 0.1602(5) 0.029(3) Uani 1 1 d . . . . .
H35 H 0.6894 0.4443 0.1316 0.035 Uiso 1 1 calc R U . . .
C41 C 1.0449(9) 0.3310(8) 0.1408(4) 0.024(3) Uani 1 1 d . . . . .
C42 C 1.1080(9) 0.2625(9) 0.1410(4) 0.030(3) Uani 1 1 d . . . . .
H42 H 1.1362 0.2427 0.1726 0.036 Uiso 1 1 calc R U . . .
C43 C 1.1304(9) 0.2226(9) 0.0954(5) 0.034(3) Uani 1 1 d . . . . .
H43 H 1.1741 0.1747 0.0949 0.040 Uiso 1 1 calc R U . . .
C44 C 1.0888(8) 0.2528(9) 0.0505(5) 0.031(3) Uani 1 1 d . . . . .
H44 H 1.1027 0.2260 0.0183 0.037 Uiso 1 1 calc R U . . .
C45 C 1.0254(8) 0.3242(8) 0.0529(4) 0.023(3) Uani 1 1 d . . . . .
H45 H 0.9962 0.3450 0.0218 0.028 Uiso 1 1 calc R U . . .
C46 C 0.8526(10) 0.4345(9) 0.8857(5) 0.040(4) Uani 1 1 d . . . . .
H46A H 0.8393 0.4768 0.9127 0.059 Uiso 1 1 calc R U . . .
H46B H 0.7894 0.4057 0.8765 0.059 Uiso 1 1 calc R U . . .
H46C H 0.8802 0.4628 0.8550 0.059 Uiso 1 1 calc R U . . .
C47 C 0.9256(11) 0.3718(9) 0.9049(5) 0.033(3) Uani 1 1 d . . . . .
N1 N 0.3663(7) 0.6777(6) 0.8749(3) 0.022(2) Uani 1 1 d . . . . .
N3 N 0.3658(7) 0.6264(6) 0.7594(3) 0.025(2) Uani 1 1 d . . . . .
N2 N 0.3668(7) 0.4932(6) 0.8444(3) 0.022(2) Uani 1 1 d . . . . .
N4 N 0.2494(7) 0.5708(6) 0.0512(4) 0.024(2) Uani 1 1 d . . . . .
N6 N 0.4705(7) 0.5625(6) 0.0405(3) 0.023(2) Uani 1 1 d . . . . .
N5 N 0.3708(7) 0.4997(6) 0.1433(3) 0.021(2) Uani 1 1 d . . . . .
N8 N 1.0084(7) 0.5379(7) 0.1493(3) 0.023(2) Uani 1 1 d . . . . .
N7 N 0.8247(7) 0.4217(7) 0.1615(3) 0.026(2) Uani 1 1 d . . . . .
N9 N 1.0049(7) 0.3636(7) 0.0970(3) 0.025(2) Uani 1 1 d . . . . .
N10 N 0.9823(10) 0.3241(9) 0.9200(5) 0.047(3) Uani 1 1 d . . . . .
P1 P 0.2094(2) 0.5991(3) 0.82596(11) 0.0236(6) Uani 1 1 d . . . . .
P2 P 0.3527(2) 0.4222(2) 0.04871(10) 0.0211(6) Uani 1 1 d . . . . .
P3 P 1.0112(3) 0.3870(2) 0.20111(11) 0.0272(8) Uani 1 1 d . . . . .
S1 S 0.0633(2) 0.5991(3) 0.82605(12) 0.0331(7) Uani 1 1 d . . . . .
S2 S 0.3429(2) 0.3087(2) 0.01953(11) 0.0255(7) Uani 1 1 d . . . . .
S3 S 1.0717(3) 0.3368(3) 0.26232(12) 0.0428(9) Uani 1 1 d . . . . .
Cu1 Cu 0.44807(9) 0.60091(13) 0.82511(5) 0.0273(3) Uani 1 1 d . . . . .
Cu2 Cu 0.37109(10) 0.60502(11) 0.09707(4) 0.0244(3) Uani 1 1 d . . . . .
Cu3 Cu 0.91465(10) 0.46807(10) 0.10257(5) 0.0245(3) Uani 1 1 d . . . . .
I1 I 0.63771(5) 0.60499(5) 0.82674(2) 0.02285(15) Uani 1 1 d . . . . .
I2 I 0.37558(6) 0.75591(5) 0.12825(3) 0.0329(2) Uani 1 1 d . . . . .
I3 I 0.82665(6) 0.53952(6) 0.02935(3) 0.03014(19) 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 1.339(16) . ?
C1 N1 1.348(14) . ?
C1 P1 1.846(12) . ?
C2 C3 1.399(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(17) . ?
C4 H4 0.9500 . ?
C5 N1 1.330(15) . ?
C5 H5 0.9500 . ?
C11 N3 1.344(14) . ?
C11 C12 1.375(15) . ?
C11 P1 1.841(11) . ?
C12 C13 1.397(16) . ?
C12 H12 0.9500 . ?
C13 C14 1.368(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.362(17) . ?
C14 H14 0.9500 . ?
C15 N3 1.350(14) . ?
C15 H15 0.9500 . ?
C6 N2 1.352(14) . ?
C6 C7 1.385(17) . ?
C6 P1 1.816(12) . ?
C7 C8 1.384(17) . ?
C7 H7 0.9500 . ?
C8 C9 1.359(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.398(18) . ?
C9 H9 0.9500 . ?
C10 N2 1.343(15) . ?
C10 H10 0.9500 . ?
C16 N4 1.338(14) . ?
C16 C17 1.384(16) . ?
C16 P2 1.832(13) . ?
C17 C18 1.373(16) . ?
C17 H17 0.9500 . ?
C18 C19 1.399(19) . ?
C18 H18 0.9500 . ?
C19 C20 1.380(15) . ?
C19 H19 0.9500 . ?
C20 N4 1.335(14) . ?
C20 H20 0.9500 . ?
C26 N6 1.333(14) . ?
C26 C27 1.384(15) . ?
C26 P2 1.832(12) . ?
C27 C28 1.373(16) . ?
C27 H27 0.9500 . ?
C28 C29 1.381(17) . ?
C28 H28 0.9500 . ?
C29 C30 1.375(15) . ?
C29 H29 0.9500 . ?
C30 N6 1.352(14) . ?
C30 H30 0.9500 . ?
C21 N5 1.366(14) . ?
C21 C22 1.398(16) . ?
C21 P2 1.831(11) . ?
C22 C23 1.379(14) . ?
C22 H22 0.9500 . ?
C23 C24 1.388(17) . ?
C23 H23 0.9500 . ?
C24 C25 1.388(17) . ?
C24 H24 0.9500 . ?
C25 N5 1.339(13) . ?
C25 H25 0.9500 . ?
C36 N8 1.352(14) . ?
C36 C37 1.400(16) . ?
C36 P3 1.826(13) . ?
C37 C38 1.369(19) . ?
C37 H37 0.9500 . ?
C38 C39 1.388(17) . ?
C38 H38 0.9500 . ?
C39 C40 1.359(16) . ?
C39 H39 0.9500 . ?
C40 N8 1.331(16) . ?
C40 H40 0.9500 . ?
C31 N7 1.344(14) . ?
C31 C32 1.390(17) . ?
C31 P3 1.833(14) . ?
C32 C33 1.392(19) . ?
C32 H32 0.9500 . ?
C33 C34 1.37(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.389(18) . ?
C34 H34 0.9500 . ?
C35 N7 1.340(14) . ?
C35 H35 0.9500 . ?
C41 N9 1.350(14) . ?
C41 C42 1.363(18) . ?
C41 P3 1.842(12) . ?
C42 C43 1.365(17) . ?
C42 H42 0.9500 . ?
C43 C44 1.368(17) . ?
C43 H43 0.9500 . ?
C44 C45 1.403(18) . ?
C44 H44 0.9500 . ?
C45 N9 1.323(14) . ?
C45 H45 0.9500 . ?
C46 C47 1.47(2) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C47 N10 1.129(17) . ?
N1 Cu1 2.069(9) . ?
N3 Cu1 2.056(9) . ?
N2 Cu1 2.068(10) . ?
N4 Cu2 2.070(9) . ?
N6 Cu2 2.075(9) . ?
N5 Cu2 2.041(9) . ?
N8 Cu3 2.048(9) . ?
N7 Cu3 2.064(9) . ?
N9 Cu3 2.036(11) . ?
P1 S1 1.935(3) . ?
P2 S2 1.940(4) . ?
P3 S3 1.938(4) . ?
Cu1 I1 2.5122(14) . ?
Cu2 I2 2.5056(18) . ?
Cu3 I3 2.4875(15) . ?

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 N1 123.4(11) . . ?
C2 C1 P1 119.9(9) . . ?
N1 C1 P1 116.4(9) . . ?
C1 C2 C3 119.8(11) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 117.5(12) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C3 C4 C5 119.0(12) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 122.9(11) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
N3 C11 C12 124.2(10) . . ?
N3 C11 P1 116.7(8) . . ?
C12 C11 P1 119.0(9) . . ?
C11 C12 C13 118.2(11) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 H12 120.9 . . ?
C14 C13 C12 118.8(11) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C15 C14 C13 118.6(11) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
N3 C15 C14 125.0(12) . . ?
N3 C15 H15 117.5 . . ?
C14 C15 H15 117.5 . . ?
N2 C6 C7 122.5(11) . . ?
N2 C6 P1 117.0(9) . . ?
C7 C6 P1 120.5(9) . . ?
C8 C7 C6 119.2(12) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C9 C8 C7 118.8(13) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 119.7(12) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
N2 C10 C9 122.1(11) . . ?
N2 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
N4 C16 C17 123.0(12) . . ?
N4 C16 P2 116.5(9) . . ?
C17 C16 P2 120.2(9) . . ?
C18 C17 C16 118.3(12) . . ?
C18 C17 H17 120.8 . . ?
C16 C17 H17 120.8 . . ?
C17 C18 C19 119.2(11) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C20 C19 C18 118.6(11) . . ?
C20 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
N4 C20 C19 122.4(11) . . ?
N4 C20 H20 118.8 . . ?
C19 C20 H20 118.8 . . ?
N6 C26 C27 123.2(11) . . ?
N6 C26 P2 116.9(8) . . ?
C27 C26 P2 119.2(9) . . ?
C28 C27 C26 118.3(12) . . ?
C28 C27 H27 120.9 . . ?
C26 C27 H27 120.9 . . ?
C27 C28 C29 119.9(11) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C30 C29 C28 118.0(11) . . ?
C30 C29 H29 121.0 . . ?
C28 C29 H29 121.0 . . ?
N6 C30 C29 123.1(12) . . ?
N6 C30 H30 118.4 . . ?
C29 C30 H30 118.4 . . ?
N5 C21 C22 123.4(10) . . ?
N5 C21 P2 117.2(8) . . ?
C22 C21 P2 119.4(8) . . ?
C23 C22 C21 117.4(11) . . ?
C23 C22 H22 121.3 . . ?
C21 C22 H22 121.3 . . ?
C22 C23 C24 120.5(11) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C25 C24 C23 117.9(10) . . ?
C25 C24 H24 121.0 . . ?
C23 C24 H24 121.0 . . ?
N5 C25 C24 123.9(11) . . ?
N5 C25 H25 118.1 . . ?
C24 C25 H25 118.1 . . ?
N8 C36 C37 121.7(11) . . ?
N8 C36 P3 117.2(8) . . ?
C37 C36 P3 121.0(9) . . ?
C38 C37 C36 118.7(11) . . ?
C38 C37 H37 120.6 . . ?
C36 C37 H37 120.6 . . ?
C37 C38 C39 119.1(11) . . ?
C37 C38 H38 120.4 . . ?
C39 C38 H38 120.4 . . ?
C40 C39 C38 118.9(12) . . ?
C40 C39 H39 120.6 . . ?
C38 C39 H39 120.6 . . ?
N8 C40 C39 123.7(10) . . ?
N8 C40 H40 118.1 . . ?
C39 C40 H40 118.1 . . ?
N7 C31 C32 122.6(12) . . ?
N7 C31 P3 117.5(8) . . ?
C32 C31 P3 119.9(10) . . ?
C31 C32 C33 117.4(13) . . ?
C31 C32 H32 121.3 . . ?
C33 C32 H32 121.3 . . ?
C34 C33 C32 120.5(13) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C33 C34 C35 118.6(13) . . ?
C33 C34 H34 120.7 . . ?
C35 C34 H34 120.7 . . ?
N7 C35 C34 122.1(12) . . ?
N7 C35 H35 118.9 . . ?
C34 C35 H35 118.9 . . ?
N9 C41 C42 122.9(11) . . ?
N9 C41 P3 115.5(9) . . ?
C42 C41 P3 121.5(9) . . ?
C41 C42 C43 119.6(11) . . ?
C41 C42 H42 120.2 . . ?
C43 C42 H42 120.2 . . ?
C42 C43 C44 118.8(12) . . ?
C42 C43 H43 120.6 . . ?
C44 C43 H43 120.6 . . ?
C43 C44 C45 118.8(11) . . ?
C43 C44 H44 120.6 . . ?
C45 C44 H44 120.6 . . ?
N9 C45 C44 122.4(11) . . ?
N9 C45 H45 118.8 . . ?
C44 C45 H45 118.8 . . ?
C47 C46 H46A 109.5 . . ?
C47 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C47 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
N10 C47 C46 179.3(15) . . ?
C5 N1 C1 117.3(10) . . ?
C5 N1 Cu1 124.3(8) . . ?
C1 N1 Cu1 118.3(8) . . ?
C11 N3 C15 115.2(10) . . ?
C11 N3 Cu1 118.4(7) . . ?
C15 N3 Cu1 125.7(8) . . ?
C10 N2 C6 117.7(11) . . ?
C10 N2 Cu1 124.0(8) . . ?
C6 N2 Cu1 118.2(8) . . ?
C20 N4 C16 118.4(10) . . ?
C20 N4 Cu2 123.1(8) . . ?
C16 N4 Cu2 118.4(8) . . ?
C26 N6 C30 117.4(10) . . ?
C26 N6 Cu2 118.0(7) . . ?
C30 N6 Cu2 124.1(8) . . ?
C25 N5 C21 116.8(10) . . ?
C25 N5 Cu2 125.9(8) . . ?
C21 N5 Cu2 117.2(7) . . ?
C40 N8 C36 117.8(9) . . ?
C40 N8 Cu3 125.1(7) . . ?
C36 N8 Cu3 116.8(8) . . ?
C35 N7 C31 118.7(10) . . ?
C35 N7 Cu3 124.6(8) . . ?
C31 N7 Cu3 116.4(8) . . ?
C45 N9 C41 117.5(11) . . ?
C45 N9 Cu3 124.0(8) . . ?
C41 N9 Cu3 118.5(8) . . ?
C6 P1 C11 104.2(5) . . ?
C6 P1 C1 104.1(5) . . ?
C11 P1 C1 106.9(6) . . ?
C6 P1 S1 113.9(4) . . ?
C11 P1 S1 113.5(4) . . ?
C1 P1 S1 113.4(4) . . ?
C21 P2 C26 108.5(5) . . ?
C21 P2 C16 106.2(5) . . ?
C26 P2 C16 100.9(5) . . ?
C21 P2 S2 113.2(4) . . ?
C26 P2 S2 113.1(4) . . ?
C16 P2 S2 114.0(4) . . ?
C36 P3 C31 107.0(6) . . ?
C36 P3 C41 104.8(5) . . ?
C31 P3 C41 104.1(5) . . ?
C36 P3 S3 113.3(4) . . ?
C31 P3 S3 113.6(4) . . ?
C41 P3 S3 113.2(4) . . ?
N3 Cu1 N2 94.8(4) . . ?
N3 Cu1 N1 96.9(4) . . ?
N2 Cu1 N1 93.2(4) . . ?
N3 Cu1 I1 122.6(3) . . ?
N2 Cu1 I1 122.5(3) . . ?
N1 Cu1 I1 119.9(3) . . ?
N5 Cu2 N4 97.0(4) . . ?
N5 Cu2 N6 98.7(4) . . ?
N4 Cu2 N6 90.5(3) . . ?
N5 Cu2 I2 125.5(3) . . ?
N4 Cu2 I2 116.6(3) . . ?
N6 Cu2 I2 121.0(3) . . ?
N9 Cu3 N8 96.8(4) . . ?
N9 Cu3 N7 96.1(4) . . ?
N8 Cu3 N7 96.0(4) . . ?
N9 Cu3 I3 125.8(3) . . ?
N8 Cu3 I3 119.2(3) . . ?
N7 Cu3 I3 116.7(3) . . ?

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 C1 C2 C3 1.0(19) . . . . ?
P1 C1 C2 C3 174.6(9) . . . . ?
C1 C2 C3 C4 -0.3(18) . . . . ?
C2 C3 C4 C5 0.4(18) . . . . ?
C3 C4 C5 N1 -1(2) . . . . ?
N3 C11 C12 C13 1.3(19) . . . . ?
P1 C11 C12 C13 -176.6(9) . . . . ?
C11 C12 C13 C14 -1.0(18) . . . . ?
C12 C13 C14 C15 -0.3(19) . . . . ?
C13 C14 C15 N3 2(2) . . . . ?
N2 C6 C7 C8 0.4(16) . . . . ?
P1 C6 C7 C8 -177.6(8) . . . . ?
C6 C7 C8 C9 -0.8(16) . . . . ?
C7 C8 C9 C10 -0.8(17) . . . . ?
C8 C9 C10 N2 2.8(17) . . . . ?
N4 C16 C17 C18 -0.9(17) . . . . ?
P2 C16 C17 C18 -174.1(8) . . . . ?
C16 C17 C18 C19 0.8(16) . . . . ?
C17 C18 C19 C20 -1.1(16) . . . . ?
C18 C19 C20 N4 1.6(16) . . . . ?
N6 C26 C27 C28 -0.2(17) . . . . ?
P2 C26 C27 C28 169.6(8) . . . . ?
C26 C27 C28 C29 -1.3(17) . . . . ?
C27 C28 C29 C30 3.0(17) . . . . ?
C28 C29 C30 N6 -3.5(17) . . . . ?
N5 C21 C22 C23 1.8(17) . . . . ?
P2 C21 C22 C23 -178.0(9) . . . . ?
C21 C22 C23 C24 -1.3(18) . . . . ?
C22 C23 C24 C25 0.6(18) . . . . ?
C23 C24 C25 N5 -0.4(18) . . . . ?
N8 C36 C37 C38 -1.0(17) . . . . ?
P3 C36 C37 C38 176.4(9) . . . . ?
C36 C37 C38 C39 0.3(17) . . . . ?
C37 C38 C39 C40 1.3(17) . . . . ?
C38 C39 C40 N8 -2.4(17) . . . . ?
N7 C31 C32 C33 -0.3(19) . . . . ?
P3 C31 C32 C33 -178.5(10) . . . . ?
C31 C32 C33 C34 0(2) . . . . ?
C32 C33 C34 C35 0(2) . . . . ?
C33 C34 C35 N7 -1(2) . . . . ?
N9 C41 C42 C43 -2.0(19) . . . . ?
P3 C41 C42 C43 179.6(9) . . . . ?
C41 C42 C43 C44 0.2(19) . . . . ?
C42 C43 C44 C45 0.6(18) . . . . ?
C43 C44 C45 N9 0.4(18) . . . . ?
C4 C5 N1 C1 1.6(19) . . . . ?
C4 C5 N1 Cu1 179.0(9) . . . . ?
C2 C1 N1 C5 -1.6(19) . . . . ?
P1 C1 N1 C5 -175.4(9) . . . . ?
C2 C1 N1 Cu1 -179.2(9) . . . . ?
P1 C1 N1 Cu1 7.0(12) . . . . ?
C12 C11 N3 C15 -0.1(18) . . . . ?
P1 C11 N3 C15 177.8(8) . . . . ?
C12 C11 N3 Cu1 -171.3(10) . . . . ?
P1 C11 N3 Cu1 6.6(13) . . . . ?
C14 C15 N3 C11 -1.4(17) . . . . ?
C14 C15 N3 Cu1 169.1(10) . . . . ?
C9 C10 N2 C6 -3.1(15) . . . . ?
C9 C10 N2 Cu1 171.6(8) . . . . ?
C7 C6 N2 C10 1.5(15) . . . . ?
P1 C6 N2 C10 179.6(8) . . . . ?
C7 C6 N2 Cu1 -173.6(8) . . . . ?
P1 C6 N2 Cu1 4.5(11) . . . . ?
C19 C20 N4 C16 -1.7(16) . . . . ?
C19 C20 N4 Cu2 173.6(8) . . . . ?
C17 C16 N4 C20 1.3(16) . . . . ?
P2 C16 N4 C20 174.7(8) . . . . ?
C17 C16 N4 Cu2 -174.2(8) . . . . ?
P2 C16 N4 Cu2 -0.7(11) . . . . ?
C27 C26 N6 C30 -0.2(16) . . . . ?
P2 C26 N6 C30 -170.2(8) . . . . ?
C27 C26 N6 Cu2 171.7(8) . . . . ?
P2 C26 N6 Cu2 1.7(10) . . . . ?
C29 C30 N6 C26 2.1(16) . . . . ?
C29 C30 N6 Cu2 -169.2(8) . . . . ?
C24 C25 N5 C21 0.8(17) . . . . ?
C24 C25 N5 Cu2 177.9(9) . . . . ?
C22 C21 N5 C25 -1.6(16) . . . . ?
P2 C21 N5 C25 178.3(8) . . . . ?
C22 C21 N5 Cu2 -178.9(8) . . . . ?
P2 C21 N5 Cu2 1.0(11) . . . . ?
C39 C40 N8 C36 1.7(16) . . . . ?
C39 C40 N8 Cu3 -171.6(8) . . . . ?
C37 C36 N8 C40 0.0(16) . . . . ?
P3 C36 N8 C40 -177.5(8) . . . . ?
C37 C36 N8 Cu3 173.9(8) . . . . ?
P3 C36 N8 Cu3 -3.6(11) . . . . ?
C34 C35 N7 C31 0.8(19) . . . . ?
C34 C35 N7 Cu3 175.0(10) . . . . ?
C32 C31 N7 C35 -0.2(18) . . . . ?
P3 C31 N7 C35 178.1(9) . . . . ?
C32 C31 N7 Cu3 -174.9(10) . . . . ?
P3 C31 N7 Cu3 3.4(13) . . . . ?
C44 C45 N9 C41 -2.1(17) . . . . ?
C44 C45 N9 Cu3 179.3(8) . . . . ?
C42 C41 N9 C45 3.0(17) . . . . ?
P3 C41 N9 C45 -178.6(8) . . . . ?
C42 C41 N9 Cu3 -178.4(9) . . . . ?
P3 C41 N9 Cu3 0.0(11) . . . . ?
N2 C6 P1 C11 52.8(9) . . . . ?
C7 C6 P1 C11 -129.1(9) . . . . ?
N2 C6 P1 C1 -59.1(9) . . . . ?
C7 C6 P1 C1 119.1(9) . . . . ?
N2 C6 P1 S1 177.0(7) . . . . ?
C7 C6 P1 S1 -4.9(10) . . . . ?
N3 C11 P1 C6 -60.1(11) . . . . ?
C12 C11 P1 C6 117.9(10) . . . . ?
N3 C11 P1 C1 49.7(11) . . . . ?
C12 C11 P1 C1 -132.3(10) . . . . ?
N3 C11 P1 S1 175.4(8) . . . . ?
C12 C11 P1 S1 -6.6(12) . . . . ?
C2 C1 P1 C6 -122.1(10) . . . . ?
N1 C1 P1 C6 51.9(10) . . . . ?
C2 C1 P1 C11 128.0(10) . . . . ?
N1 C1 P1 C11 -58.0(10) . . . . ?
C2 C1 P1 S1 2.2(12) . . . . ?
N1 C1 P1 S1 176.2(8) . . . . ?
N5 C21 P2 C26 52.3(10) . . . . ?
C22 C21 P2 C26 -127.9(9) . . . . ?
N5 C21 P2 C16 -55.4(9) . . . . ?
C22 C21 P2 C16 124.4(9) . . . . ?
N5 C21 P2 S2 178.7(7) . . . . ?
C22 C21 P2 S2 -1.4(10) . . . . ?
N6 C26 P2 C21 -53.7(9) . . . . ?
C27 C26 P2 C21 135.9(9) . . . . ?
N6 C26 P2 C16 57.7(9) . . . . ?
C27 C26 P2 C16 -112.8(9) . . . . ?
N6 C26 P2 S2 179.8(7) . . . . ?
C27 C26 P2 S2 9.4(10) . . . . ?
N4 C16 P2 C21 54.9(10) . . . . ?
C17 C16 P2 C21 -131.5(9) . . . . ?
N4 C16 P2 C26 -58.2(9) . . . . ?
C17 C16 P2 C26 115.4(9) . . . . ?
N4 C16 P2 S2 -179.8(7) . . . . ?
C17 C16 P2 S2 -6.1(10) . . . . ?
N8 C36 P3 C31 -51.8(10) . . . . ?
C37 C36 P3 C31 130.7(9) . . . . ?
N8 C36 P3 C41 58.3(10) . . . . ?
C37 C36 P3 C41 -119.2(10) . . . . ?
N8 C36 P3 S3 -177.8(7) . . . . ?
C37 C36 P3 S3 4.7(11) . . . . ?
N7 C31 P3 C36 51.9(11) . . . . ?
C32 C31 P3 C36 -129.9(10) . . . . ?
N7 C31 P3 C41 -58.7(11) . . . . ?
C32 C31 P3 C41 119.5(10) . . . . ?
N7 C31 P3 S3 177.7(8) . . . . ?
C32 C31 P3 S3 -4.0(12) . . . . ?
N9 C41 P3 C36 -55.8(10) . . . . ?
C42 C41 P3 C36 122.6(10) . . . . ?
N9 C41 P3 C31 56.4(10) . . . . ?
C42 C41 P3 C31 -125.2(10) . . . . ?
N9 C41 P3 S3 -179.8(7) . . . . ?
C42 C41 P3 S3 -1.3(12) . . . . ?

_refine_diff_density_max         1.097
_refine_diff_density_min         -0.665
_refine_diff_density_rms         0.114

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
#######################################################################
#
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#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_tgv41

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
Iodo tris(2-pyridyl)phosphineselenide copper(I)
;
_chemical_name_common            'C7, CuItpypse'
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 Cu1 I1 N3 P1 Se1, 2.5(C2 H3 N)'
_chemical_formula_sum            'C20 H19.50 Cu I N5.50 P Se'
_chemical_formula_weight         637.28

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'
P P 0.1023 0.0942 '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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/a'
_space_group_name_Hall           '-P 2yab'

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

_cell_length_a                   8.7685(3)
_cell_length_b                   15.6075(5)
_cell_length_c                   18.0144(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.011(3)
_cell_angle_gamma                90
_cell_volume                     2392.00(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11076
_cell_measurement_theta_min      1.75
_cell_measurement_theta_max      27.16

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.770
_exptl_crystal_F_000             1236
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    3.809
_shelx_estimated_absorpt_T_min   0.285
_shelx_estimated_absorpt_T_max   0.863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4536
_exptl_absorpt_correction_T_max  0.6916
_exptl_absorpt_process_details   
; 
R. H. Blessing, Acta Cryst. A 1995, 51, 33-38.
;

_exptl_special_details           ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   
;
sealed X-ray tube, 12 x 0.4 mm long-fine focus
;
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            13242
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.749
_diffrn_reflns_theta_max         26.724
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5056
_reflns_number_gt                3816
_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       
;
Stoe & Cie: X-AREA v1.56, Stoe & Cie GmbH, Darmstadt, Germany, 2011
;
_computing_cell_refinement       
;
Stoe & Cie: X-AREA v1.56, Stoe & Cie GmbH, Darmstadt, Germany, 2011
;
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    
;
SIR97 (A. Altomare, M. C. Burla, M. Camalli, G. Cascarano, C. Giacovazzo, 
A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, 
J. Appl. Crystallogr. 1999, 32, 115-119.)
;
_computing_structure_refinement  
;
SHELXL-2014 (G. Sheldrick, Acta Cryst. A 2008, 64, 112-122)
;
_computing_molecular_graphics    
;
K. Brandenburg, H. Putz: 
Diamond - Crystal and Molecular Structure Visualization v3.2i, 
Crystal Impact GbR, Bonn, Germany, 2012
;
_computing_publication_material  
;
WinGX publication routines (L. Farrugia, 
J. Appl. Crystallogr. 1999, 32, 837-838.)
;
_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)+(0.0315P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5056
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0613
_refine_ls_wR_factor_gt          0.0592
_refine_ls_goodness_of_fit_ref   0.865
_refine_ls_restrained_S_all      0.865
_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 0.08105(3) 0.67356(2) 0.84313(2) 0.02517(7) Uani 1 1 d . . . . .
Se1 Se 0.38158(4) 0.24393(2) 0.72295(2) 0.02678(9) Uani 1 1 d . . . . .
Cu1 Cu 0.17034(5) 0.53133(3) 0.80799(2) 0.02495(10) Uani 1 1 d . . . . .
P1 P 0.29790(11) 0.35961(5) 0.75822(5) 0.01939(18) Uani 1 1 d . . . . .
C7 C 0.0886(4) 0.3692(2) 0.61304(19) 0.0263(8) Uani 1 1 d . . . . .
H7 H 0.1373 0.3183 0.6011 0.032 Uiso 1 1 calc R U . . .
C12 C 0.2512(5) 0.2761(2) 0.8880(2) 0.0306(9) Uani 1 1 d . . . . .
H12 H 0.2986 0.2278 0.8705 0.037 Uiso 1 1 calc R U . . .
C2 C 0.6019(4) 0.4280(2) 0.7769(2) 0.0268(8) Uani 1 1 d . . . . .
H2 H 0.6319 0.3733 0.7620 0.032 Uiso 1 1 calc R U . . .
C1 C 0.4492(4) 0.4437(2) 0.78066(18) 0.0236(7) Uani 1 1 d . . . . .
N1 N 0.4003(4) 0.51981(19) 0.80166(16) 0.0252(6) Uani 1 1 d . . . . .
C10 C -0.0441(4) 0.5160(3) 0.6502(2) 0.0294(8) Uani 1 1 d . . . . .
H10 H -0.0901 0.5675 0.6627 0.035 Uiso 1 1 calc R U . . .
N2 N 0.0728(3) 0.47992(18) 0.70292(16) 0.0239(6) Uani 1 1 d . . . . .
C19 C 0.3033(5) 0.7482(3) 0.5990(2) 0.0357(9) Uani 1 1 d . . . . .
C6 C 0.1369(4) 0.4070(2) 0.68450(18) 0.0219(7) Uani 1 1 d . . . . .
N3 N 0.1648(4) 0.42131(19) 0.86901(16) 0.0256(7) Uani 1 1 d . . . . .
C11 C 0.2292(4) 0.3510(2) 0.84658(18) 0.0234(7) Uani 1 1 d . . . . .
C9 C -0.1000(5) 0.4808(3) 0.5786(2) 0.0333(9) Uani 1 1 d . . . . .
H9 H -0.1845 0.5071 0.5427 0.040 Uiso 1 1 calc R U . . .
C8 C -0.0319(5) 0.4073(3) 0.5597(2) 0.0326(9) Uani 1 1 d . . . . .
H8 H -0.0676 0.3829 0.5102 0.039 Uiso 1 1 calc R U . . .
N4 N 0.4115(5) 0.5174(3) 0.5925(2) 0.0533(11) Uani 1 1 d . . . . .
C17 C 0.4613(5) 0.4526(3) 0.5808(2) 0.0378(10) Uani 1 1 d . . . . .
C13 C 0.2027(5) 0.2722(3) 0.9560(2) 0.0391(10) Uani 1 1 d . . . . .
H13 H 0.2179 0.2217 0.9863 0.047 Uiso 1 1 calc R U . . .
C4 C 0.6625(5) 0.5726(3) 0.8163(2) 0.0341(9) Uani 1 1 d . . . . .
H4 H 0.7345 0.6189 0.8285 0.041 Uiso 1 1 calc R U . . .
C14 C 0.1325(5) 0.3430(3) 0.9784(2) 0.0384(10) Uani 1 1 d . . . . .
H14 H 0.0962 0.3417 1.0240 0.046 Uiso 1 1 calc R U . . .
C18 C 0.2600(6) 0.7042(3) 0.6616(2) 0.0454(11) Uani 1 1 d . . . . .
H18A H 0.2921 0.6440 0.6621 0.068 Uiso 1 1 calc R U . . .
H18B H 0.1458 0.7074 0.6549 0.068 Uiso 1 1 calc R U . . .
H18C H 0.3126 0.7313 0.7101 0.068 Uiso 1 1 calc R U . . .
N5 N 0.3394(5) 0.7829(3) 0.5504(2) 0.0515(10) Uani 1 1 d . . . . .
C5 C 0.5073(5) 0.5829(2) 0.8194(2) 0.0293(8) Uani 1 1 d . . . . .
H5 H 0.4751 0.6369 0.8347 0.035 Uiso 1 1 calc R U . . .
C3 C 0.7110(5) 0.4940(3) 0.7953(2) 0.0320(9) Uani 1 1 d . . . . .
H3 H 0.8173 0.4851 0.7935 0.038 Uiso 1 1 calc R U . . .
C16 C 0.5221(5) 0.3695(3) 0.5642(2) 0.0418(10) Uani 1 1 d . . . . .
H16A H 0.6120 0.3537 0.6059 0.063 Uiso 1 1 calc R U . . .
H16B H 0.5555 0.3730 0.5162 0.063 Uiso 1 1 calc R U . . .
H16C H 0.4395 0.3261 0.5594 0.063 Uiso 1 1 calc R U . . .
C15 C 0.1149(5) 0.4163(3) 0.9341(2) 0.0346(9) Uani 1 1 d . . . . .
H15 H 0.0659 0.4649 0.9500 0.042 Uiso 1 1 calc R U . . .
C21 C -0.0214(14) -0.0118(7) 1.0157(6) 0.042(3) Uani 0.5 1 d . . P A -1
C20 C 0.0569(19) 0.0643(12) 0.9964(7) 0.039(3) Uani 0.5 1 d . . P A -1
H20A H 0.0909 0.0539 0.9492 0.059 Uiso 0.5 1 calc R U P A -1
H20B H 0.1487 0.0773 1.0381 0.059 Uiso 0.5 1 calc R U P A -1
H20C H -0.0162 0.1128 0.9889 0.059 Uiso 0.5 1 calc R U P A -1
N6 N -0.084(2) -0.0696(11) 1.0312(7) 0.067(5) Uani 0.5 1 d . . P A -1


_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 2.4863(5) . ?
Se1 P1 2.1042(9) . ?
Cu1 N2 2.043(3) . ?
Cu1 N3 2.046(3) . ?
Cu1 N1 2.054(3) . ?
P1 C11 1.838(4) . ?
P1 C1 1.840(4) . ?
P1 C6 1.843(4) . ?
C7 C8 1.380(5) . ?
C7 C6 1.386(5) . ?
C7 H7 0.9500 . ?
C12 C11 1.375(5) . ?
C12 C13 1.393(6) . ?
C12 H12 0.9500 . ?
C2 C1 1.379(5) . ?
C2 C3 1.390(5) . ?
C2 H2 0.9500 . ?
C1 N1 1.349(4) . ?
N1 C5 1.345(5) . ?
C10 N2 1.341(5) . ?
C10 C9 1.379(5) . ?
C10 H10 0.9500 . ?
N2 C6 1.345(4) . ?
C19 N5 1.137(5) . ?
C19 C18 1.448(6) . ?
N3 C11 1.341(5) . ?
N3 C15 1.349(5) . ?
C9 C8 1.374(6) . ?
C9 H9 0.9500 . ?
C8 H8 0.9500 . ?
N4 C17 1.142(6) . ?
C17 C16 1.460(6) . ?
C13 C14 1.372(6) . ?
C13 H13 0.9500 . ?
C4 C3 1.382(6) . ?
C4 C5 1.384(5) . ?
C4 H4 0.9500 . ?
C14 C15 1.381(6) . ?
C14 H14 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C5 H5 0.9500 . ?
C3 H3 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C15 H15 0.9500 . ?
C21 N6 1.126(18) . ?
C21 C20 1.46(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
N2 Cu1 N3 96.26(11) . . ?
N2 Cu1 N1 96.35(12) . . ?
N3 Cu1 N1 96.19(12) . . ?
N2 Cu1 I1 119.97(8) . . ?
N3 Cu1 I1 124.23(8) . . ?
N1 Cu1 I1 117.77(8) . . ?
C11 P1 C1 103.41(16) . . ?
C11 P1 C6 107.39(16) . . ?
C1 P1 C6 104.95(16) . . ?
C11 P1 Se1 114.21(12) . . ?
C1 P1 Se1 113.11(12) . . ?
C6 P1 Se1 112.91(11) . . ?
C8 C7 C6 118.3(4) . . ?
C8 C7 H7 120.9 . . ?
C6 C7 H7 120.9 . . ?
C11 C12 C13 118.8(4) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C1 C2 C3 118.5(3) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
N1 C1 C2 123.3(3) . . ?
N1 C1 P1 115.4(3) . . ?
C2 C1 P1 121.3(3) . . ?
C5 N1 C1 117.4(3) . . ?
C5 N1 Cu1 124.1(2) . . ?
C1 N1 Cu1 118.4(2) . . ?
N2 C10 C9 122.3(4) . . ?
N2 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C10 N2 C6 118.3(3) . . ?
C10 N2 Cu1 124.6(3) . . ?
C6 N2 Cu1 117.0(2) . . ?
N5 C19 C18 179.0(5) . . ?
N2 C6 C7 122.5(3) . . ?
N2 C6 P1 117.0(2) . . ?
C7 C6 P1 120.4(3) . . ?
C11 N3 C15 117.6(3) . . ?
C11 N3 Cu1 117.3(2) . . ?
C15 N3 Cu1 124.8(3) . . ?
N3 C11 C12 123.1(3) . . ?
N3 C11 P1 116.8(2) . . ?
C12 C11 P1 120.0(3) . . ?
C8 C9 C10 119.1(4) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C9 C8 C7 119.5(3) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
N4 C17 C16 178.7(5) . . ?
C14 C13 C12 118.5(4) . . ?
C14 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
C3 C4 C5 119.0(4) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C13 C14 C15 119.5(4) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C19 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C5 C4 122.8(4) . . ?
N1 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C4 C3 C2 118.9(4) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C15 C14 122.4(4) . . ?
N3 C15 H15 118.8 . . ?
C14 C15 H15 118.8 . . ?
N6 C21 C20 178.5(19) . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C3 C2 C1 N1 -0.3(5) . . . . ?
C3 C2 C1 P1 -179.3(3) . . . . ?
C11 P1 C1 N1 -57.6(3) . . . . ?
C6 P1 C1 N1 54.8(3) . . . . ?
Se1 P1 C1 N1 178.3(2) . . . . ?
C11 P1 C1 C2 121.6(3) . . . . ?
C6 P1 C1 C2 -126.0(3) . . . . ?
Se1 P1 C1 C2 -2.5(3) . . . . ?
C2 C1 N1 C5 0.2(5) . . . . ?
P1 C1 N1 C5 179.3(3) . . . . ?
C2 C1 N1 Cu1 -177.9(3) . . . . ?
P1 C1 N1 Cu1 1.2(3) . . . . ?
C9 C10 N2 C6 0.1(5) . . . . ?
C9 C10 N2 Cu1 176.4(3) . . . . ?
C10 N2 C6 C7 1.3(5) . . . . ?
Cu1 N2 C6 C7 -175.4(3) . . . . ?
C10 N2 C6 P1 179.7(3) . . . . ?
Cu1 N2 C6 P1 3.1(3) . . . . ?
C8 C7 C6 N2 -1.3(5) . . . . ?
C8 C7 C6 P1 -179.7(3) . . . . ?
C11 P1 C6 N2 51.3(3) . . . . ?
C1 P1 C6 N2 -58.3(3) . . . . ?
Se1 P1 C6 N2 178.1(2) . . . . ?
C11 P1 C6 C7 -130.2(3) . . . . ?
C1 P1 C6 C7 120.2(3) . . . . ?
Se1 P1 C6 C7 -3.4(3) . . . . ?
C15 N3 C11 C12 -2.3(5) . . . . ?
Cu1 N3 C11 C12 171.5(3) . . . . ?
C15 N3 C11 P1 -179.5(3) . . . . ?
Cu1 N3 C11 P1 -5.6(4) . . . . ?
C13 C12 C11 N3 0.8(6) . . . . ?
C13 C12 C11 P1 177.9(3) . . . . ?
C1 P1 C11 N3 61.0(3) . . . . ?
C6 P1 C11 N3 -49.6(3) . . . . ?
Se1 P1 C11 N3 -175.6(2) . . . . ?
C1 P1 C11 C12 -116.2(3) . . . . ?
C6 P1 C11 C12 133.1(3) . . . . ?
Se1 P1 C11 C12 7.1(3) . . . . ?
N2 C10 C9 C8 -1.3(6) . . . . ?
C10 C9 C8 C7 1.2(6) . . . . ?
C6 C7 C8 C9 0.0(5) . . . . ?
C11 C12 C13 C14 1.1(6) . . . . ?
C12 C13 C14 C15 -1.4(6) . . . . ?
C1 N1 C5 C4 0.4(5) . . . . ?
Cu1 N1 C5 C4 178.4(3) . . . . ?
C3 C4 C5 N1 -1.0(6) . . . . ?
C5 C4 C3 C2 0.9(6) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C11 N3 C15 C14 2.0(6) . . . . ?
Cu1 N3 C15 C14 -171.4(3) . . . . ?
C13 C14 C15 N3 -0.1(6) . . . . ?

_refine_diff_density_max         0.996
_refine_diff_density_min         -0.836
_refine_diff_density_rms         0.097

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
_database_code_depnum_ccdc_archive 'CCDC 1021443'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_tgv58
_database_code_depnum_ccdc_archive 'CCDC 1021444'
_audit_contact_author            'Joerg Sundermeyer'
_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
Iodo tris(2-pyridyl)arsineoxide copper(I)
;
_chemical_name_common            'C8; CuItpyaso'
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 As1 Cu1 I1 N3 O1, 0.75 (C2 H3 N)'
_chemical_formula_sum            'C16.50 H14.25 As Cu I N3.75 O'
_chemical_formula_weight         546.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
As As 0.0499 2.0058 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   8.7081(4)
_cell_length_b                   29.7666(14)
_cell_length_c                   14.5936(9)
_cell_angle_alpha                90
_cell_angle_beta                 105.559(4)
_cell_angle_gamma                90
_cell_volume                     3644.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    16373
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      27.22

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.992
_exptl_crystal_F_000             2100
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    4.705
_shelx_estimated_absorpt_T_min   0.352
_shelx_estimated_absorpt_T_max   0.834
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.5068
_exptl_absorpt_correction_T_max  0.8350
_exptl_absorpt_process_details   
;
HKLF5 Absorption correction, STOE X-Red32(TwinAbs) 1.47 
;
_exptl_special_details           ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   
;
sealed X-ray tube, 12 x 0.4 mm long-fine focus
;
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            35607
_diffrn_reflns_av_unetI/netI     0.1421
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.368
_diffrn_reflns_theta_max         27.167
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             35607
_reflns_number_gt                16911
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _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       
;
Stoe & Cie: X-AREA v1.56, Stoe & Cie GmbH, Darmstadt, Germany, 2011
;
_computing_cell_refinement       
;
Stoe & Cie: X-AREA v1.56, Stoe & Cie GmbH, Darmstadt, Germany, 2011
;
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    
;
SIR97 (A. Altomare, M. C. Burla, M. Camalli, G. Cascarano, C. Giacovazzo, 
A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, 
J. Appl. Crystallogr. 1999, 32, 115-119.)
;
_computing_structure_refinement  
;
SHELXL-2014 (G. Sheldrick, Acta Cryst. A 2008, 64, 112-122)
;
_computing_molecular_graphics    
;
K. Brandenburg, H. Putz: 
Diamond - Crystal and Molecular Structure Visualization v3.2i, 
Crystal Impact GbR, Bonn, Germany, 2012
;
_computing_publication_material  
;
WinGX publication routines (L. Farrugia, 
J. Appl. Crystallogr. 1999, 32, 837-838.)
;

_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0786P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         35607
_refine_ls_number_parameters     454
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1465
_refine_ls_wR_factor_gt          0.1315
_refine_ls_goodness_of_fit_ref   0.764
_refine_ls_restrained_S_all      0.764
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.1671(15) 1.0297(4) 0.7653(9) 0.035(3) Uani 1 1 d . . . . .
C2 C 1.3261(15) 1.0346(4) 0.7687(9) 0.040(3) Uani 1 1 d . . . . .
H2 H 1.3770 1.0630 0.7824 0.048 Uiso 1 1 calc R U . . .
C3 C 1.4084(15) 0.9980(4) 0.7521(10) 0.042(3) Uani 1 1 d . . . . .
H3 H 1.5186 1.0004 0.7555 0.050 Uiso 1 1 calc R U . . .
C4 C 1.3299(16) 0.9570(4) 0.7299(10) 0.040(3) Uani 1 1 d . . . . .
H4 H 1.3850 0.9313 0.7170 0.048 Uiso 1 1 calc R U . . .
C5 C 1.1704(15) 0.9545(4) 0.7271(9) 0.036(3) Uani 1 1 d . . . . .
H5 H 1.1178 0.9265 0.7123 0.043 Uiso 1 1 calc R U . . .
C11 C 0.8548(15) 1.0793(4) 0.6731(9) 0.037(3) Uani 1 1 d . . . . .
C12 C 0.8164(16) 1.1174(4) 0.6176(9) 0.040(3) Uani 1 1 d . . . . .
H12 H 0.8786 1.1439 0.6333 0.048 Uiso 1 1 calc R U . . .
C13 C 0.6857(16) 1.1163(4) 0.5387(9) 0.045(3) Uani 1 1 d . . . . .
H13 H 0.6571 1.1419 0.4989 0.054 Uiso 1 1 calc R U . . .
C14 C 0.5979(17) 1.0770(4) 0.5192(10) 0.047(3) Uani 1 1 d . . . . .
H14 H 0.5079 1.0751 0.4655 0.057 Uiso 1 1 calc R U . . .
C15 C 0.6434(16) 1.0406(4) 0.5793(9) 0.045(3) Uani 1 1 d . . . . .
H15 H 0.5802 1.0142 0.5665 0.054 Uiso 1 1 calc R U . . .
C6 C 0.9453(14) 1.0606(4) 0.8867(9) 0.034(3) Uani 1 1 d . . . . .
C7 C 0.9675(15) 1.0864(4) 0.9691(9) 0.038(3) Uani 1 1 d . . . . .
H7 H 1.0323 1.1126 0.9786 0.045 Uiso 1 1 calc R U . . .
C8 C 0.8926(15) 1.0728(4) 1.0363(9) 0.039(3) Uani 1 1 d . . . . .
H8 H 0.9053 1.0894 1.0934 0.047 Uiso 1 1 calc R U . . .
C9 C 0.7984(15) 1.0346(4) 1.0196(9) 0.040(3) Uani 1 1 d . . . . .
H9 H 0.7425 1.0255 1.0642 0.049 Uiso 1 1 calc R U . . .
C10 C 0.7858(15) 1.0098(4) 0.9380(9) 0.038(3) Uani 1 1 d . . . . .
H10 H 0.7234 0.9831 0.9288 0.045 Uiso 1 1 calc R U . . .
C26 C 0.0404(14) 0.6633(4) 0.5857(9) 0.035(3) Uani 1 1 d . . . . .
C27 C 0.0181(13) 0.6298(4) 0.5178(9) 0.039(3) Uani 1 1 d . . . . .
H27 H -0.0324 0.6024 0.5263 0.046 Uiso 1 1 calc R U . . .
C28 C 0.0697(16) 0.6365(4) 0.4380(9) 0.044(3) Uani 1 1 d . . . . .
H28 H 0.0538 0.6141 0.3900 0.053 Uiso 1 1 calc R U . . .
C29 C 0.1455(15) 0.6766(4) 0.4288(9) 0.042(3) Uani 1 1 d . . . . .
H29 H 0.1843 0.6818 0.3748 0.051 Uiso 1 1 calc R U . . .
C30 C 0.1641(15) 0.7088(4) 0.4990(9) 0.038(3) Uani 1 1 d . . . . .
H30 H 0.2162 0.7361 0.4920 0.046 Uiso 1 1 calc R U . . .
C16 C -0.1808(14) 0.7067(4) 0.6887(8) 0.032(3) Uani 1 1 d . . . . .
C17 C -0.3395(16) 0.7008(4) 0.6871(9) 0.040(3) Uani 1 1 d . . . . .
H17 H -0.3808 0.6715 0.6907 0.048 Uiso 1 1 calc R U . . .
C18 C -0.4355(15) 0.7374(4) 0.6803(9) 0.037(3) Uani 1 1 d . . . . .
H18 H -0.5448 0.7344 0.6786 0.044 Uiso 1 1 calc R U . . .
C19 C -0.3662(15) 0.7805(4) 0.6758(9) 0.035(3) Uani 1 1 d . . . . .
H19 H -0.4279 0.8071 0.6722 0.042 Uiso 1 1 calc R U . . .
C20 C -0.2097(14) 0.7827(4) 0.6766(8) 0.033(3) Uani 1 1 d . . . . .
H20 H -0.1661 0.8115 0.6716 0.040 Uiso 1 1 calc R U . . .
C21 C 0.1424(13) 0.6692(4) 0.8052(9) 0.033(3) Uani 1 1 d . . . . .
C22 C 0.1856(14) 0.6397(4) 0.8813(9) 0.037(3) Uani 1 1 d . . . . .
H22 H 0.1294 0.6124 0.8817 0.044 Uiso 1 1 calc R U . . .
C23 C 0.3132(15) 0.6514(4) 0.9567(9) 0.041(3) Uani 1 1 d . . . . .
H23 H 0.3458 0.6322 1.0105 0.049 Uiso 1 1 calc R U . . .
C24 C 0.3921(15) 0.6908(4) 0.9532(9) 0.042(3) Uani 1 1 d . . . . .
H24 H 0.4805 0.6991 1.0044 0.050 Uiso 1 1 calc R U . . .
C25 C 0.3426(14) 0.7186(4) 0.8747(9) 0.037(3) Uani 1 1 d . . . . .
H25 H 0.3986 0.7459 0.8732 0.044 Uiso 1 1 calc R U . . .
C31 C 0.425(2) 0.3001(5) 0.5802(12) 0.067(5) Uani 1 1 d . . . . .
H31A H 0.3785 0.3005 0.6343 0.101 Uiso 1 1 calc R U . . .
H31B H 0.3404 0.3030 0.5208 0.101 Uiso 1 1 calc R U . . .
H31C H 0.5002 0.3251 0.5858 0.101 Uiso 1 1 calc R U . . .
C32 C 0.5086(18) 0.2582(5) 0.5797(10) 0.050(4) Uani 1 1 d . . . . .
N1 N 1.0854(11) 0.9899(4) 0.7444(7) 0.035(2) Uani 1 1 d . . . . .
N3 N 0.7716(12) 1.0406(3) 0.6545(7) 0.039(2) Uani 1 1 d . . . . .
N2 N 0.8585(11) 1.0219(3) 0.8710(7) 0.035(2) Uani 1 1 d . . . . .
N6 N 0.1115(11) 0.7032(3) 0.5768(7) 0.033(2) Uani 1 1 d . . . . .
N4 N -0.1124(11) 0.7472(3) 0.6838(7) 0.031(2) Uani 1 1 d . . . . .
N5 N 0.2172(12) 0.7083(3) 0.8001(7) 0.034(2) Uani 1 1 d . . . . .
N7 N 0.5789(15) 0.2256(4) 0.5802(8) 0.051(3) Uani 1 1 d . . . . .
O1 O 1.1289(10) 1.1272(3) 0.8066(6) 0.039(2) Uani 1 1 d . . . . .
O2 O -0.1172(9) 0.6071(2) 0.7018(6) 0.0360(19) Uani 1 1 d . . . . .
Cu1 Cu 0.85009(17) 0.98799(5) 0.74640(11) 0.0354(4) Uani 1 1 d . . . . .
Cu2 Cu 0.12432(17) 0.74892(5) 0.68457(11) 0.0332(3) Uani 1 1 d . . . . .
As1 As 1.03501(15) 1.07911(4) 0.78491(9) 0.0340(3) Uani 1 1 d . . . . .
As2 As -0.03658(14) 0.65628(4) 0.69721(9) 0.0319(3) Uani 1 1 d . . . . .
I1 I 0.74507(10) 0.90905(2) 0.72832(6) 0.0382(2) Uani 1 1 d . . . . .
I2 I 0.23221(9) 0.82773(2) 0.69322(6) 0.0358(2) Uani 1 1 d . . . . .
N8 N 1.140(5) 1.0378(13) 0.532(3) 0.073(11) Uani 0.5 1 d . . P A -1
C33 C 0.940(8) 0.9696(18) 0.496(4) 0.063(14) Uani 0.5 1 d . . P A -1
H33A H 0.9874 0.9445 0.4697 0.094 Uiso 0.5 1 calc R U P A -1
H33B H 0.8396 0.9784 0.4514 0.094 Uiso 0.5 1 calc R U P A -1
H33C H 0.9203 0.9602 0.5565 0.094 Uiso 0.5 1 calc R U P A -1
C34 C 1.050(8) 1.0074(13) 0.513(4) 0.059(12) Uani 0.5 1 d . . P A -1


_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 1.372(15) . ?
C1 C2 1.380(16) . ?
C1 As1 1.936(12) . ?
C2 C3 1.362(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(16) . ?
C4 H4 0.9500 . ?
C5 N1 1.350(15) . ?
C5 H5 0.9500 . ?
C11 N3 1.351(15) . ?
C11 C12 1.380(16) . ?
C11 As1 1.936(13) . ?
C12 C13 1.385(18) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(17) . ?
C14 H14 0.9500 . ?
C15 N3 1.339(16) . ?
C15 H15 0.9500 . ?
C6 N2 1.363(15) . ?
C6 C7 1.397(17) . ?
C6 As1 1.935(12) . ?
C7 C8 1.376(17) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.380(17) . ?
C9 H9 0.9500 . ?
C10 N2 1.350(15) . ?
C10 H10 0.9500 . ?
C26 N6 1.360(14) . ?
C26 C27 1.383(16) . ?
C26 As2 1.930(12) . ?
C27 C28 1.370(17) . ?
C27 H27 0.9500 . ?
C28 C29 1.388(18) . ?
C28 H28 0.9500 . ?
C29 C30 1.381(17) . ?
C29 H29 0.9500 . ?
C30 N6 1.344(15) . ?
C30 H30 0.9500 . ?
C16 N4 1.354(15) . ?
C16 C17 1.387(16) . ?
C16 As2 1.941(12) . ?
C17 C18 1.362(17) . ?
C17 H17 0.9500 . ?
C18 C19 1.427(16) . ?
C18 H18 0.9500 . ?
C19 C20 1.361(16) . ?
C19 H19 0.9500 . ?
C20 N4 1.340(15) . ?
C20 H20 0.9500 . ?
C21 N5 1.347(14) . ?
C21 C22 1.386(16) . ?
C21 As2 1.935(12) . ?
C22 C23 1.382(17) . ?
C22 H22 0.9500 . ?
C23 C24 1.368(17) . ?
C23 H23 0.9500 . ?
C24 C25 1.385(17) . ?
C24 H24 0.9500 . ?
C25 N5 1.354(15) . ?
C25 H25 0.9500 . ?
C31 C32 1.44(2) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 N7 1.146(17) . ?
N1 Cu1 2.058(9) . ?
N3 Cu1 2.055(10) . ?
N2 Cu1 2.063(10) . ?
N6 Cu2 2.061(10) . ?
N4 Cu2 2.059(9) . ?
N5 Cu2 2.055(10) . ?
O1 As1 1.636(8) . ?
O2 As2 1.633(7) . ?
Cu1 I1 2.5096(17) . ?
Cu2 I2 2.5176(16) . ?
N8 C34 1.18(5) . ?
C33 C34 1.45(6) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 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
N1 C1 C2 123.8(11) . . ?
N1 C1 As1 113.3(8) . . ?
C2 C1 As1 122.9(9) . . ?
C3 C2 C1 118.7(12) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 119.5(12) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 118.8(11) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C5 C4 123.4(12) . . ?
N1 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
N3 C11 C12 123.4(12) . . ?
N3 C11 As1 115.8(9) . . ?
C12 C11 As1 120.8(10) . . ?
C11 C12 C13 119.0(12) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C14 C13 C12 118.5(12) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C13 C14 C15 118.8(12) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
N3 C15 C14 123.6(12) . . ?
N3 C15 H15 118.2 . . ?
C14 C15 H15 118.2 . . ?
N2 C6 C7 123.6(11) . . ?
N2 C6 As1 115.6(9) . . ?
C7 C6 As1 120.9(9) . . ?
C8 C7 C6 117.9(12) . . ?
C8 C7 H7 121.0 . . ?
C6 C7 H7 121.0 . . ?
C7 C8 C9 119.2(12) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 119.8(12) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
N2 C10 C9 122.6(12) . . ?
N2 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
N6 C26 C27 122.7(11) . . ?
N6 C26 As2 116.4(8) . . ?
C27 C26 As2 120.8(9) . . ?
C28 C27 C26 119.3(12) . . ?
C28 C27 H27 120.4 . . ?
C26 C27 H27 120.4 . . ?
C27 C28 C29 118.7(12) . . ?
C27 C28 H28 120.6 . . ?
C29 C28 H28 120.6 . . ?
C30 C29 C28 119.3(12) . . ?
C30 C29 H29 120.3 . . ?
C28 C29 H29 120.3 . . ?
N6 C30 C29 122.7(11) . . ?
N6 C30 H30 118.6 . . ?
C29 C30 H30 118.6 . . ?
N4 C16 C17 124.3(11) . . ?
N4 C16 As2 113.9(8) . . ?
C17 C16 As2 121.8(9) . . ?
C18 C17 C16 119.2(12) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C17 C18 C19 117.7(12) . . ?
C17 C18 H18 121.1 . . ?
C19 C18 H18 121.1 . . ?
C20 C19 C18 118.4(11) . . ?
C20 C19 H19 120.8 . . ?
C18 C19 H19 120.8 . . ?
N4 C20 C19 125.1(12) . . ?
N4 C20 H20 117.5 . . ?
C19 C20 H20 117.5 . . ?
N5 C21 C22 124.1(11) . . ?
N5 C21 As2 115.0(8) . . ?
C22 C21 As2 120.9(9) . . ?
C23 C22 C21 117.8(11) . . ?
C23 C22 H22 121.1 . . ?
C21 C22 H22 121.1 . . ?
C24 C23 C22 119.3(12) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C23 C24 C25 119.7(11) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
N5 C25 C24 122.3(11) . . ?
N5 C25 H25 118.8 . . ?
C24 C25 H25 118.8 . . ?
C32 C31 H31A 109.5 . . ?
C32 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C32 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N7 C32 C31 178.0(17) . . ?
C5 N1 C1 115.9(10) . . ?
C5 N1 Cu1 125.4(9) . . ?
C1 N1 Cu1 118.7(8) . . ?
C15 N3 C11 116.6(11) . . ?
C15 N3 Cu1 126.4(8) . . ?
C11 N3 Cu1 116.9(8) . . ?
C10 N2 C6 116.7(10) . . ?
C10 N2 Cu1 126.6(8) . . ?
C6 N2 Cu1 116.7(8) . . ?
C30 N6 C26 117.2(10) . . ?
C30 N6 Cu2 126.9(8) . . ?
C26 N6 Cu2 115.9(8) . . ?
C20 N4 C16 115.2(10) . . ?
C20 N4 Cu2 126.3(9) . . ?
C16 N4 Cu2 118.4(8) . . ?
C21 N5 C25 116.7(10) . . ?
C21 N5 Cu2 117.7(8) . . ?
C25 N5 Cu2 125.6(8) . . ?
N3 Cu1 N1 97.3(4) . . ?
N3 Cu1 N2 97.4(4) . . ?
N1 Cu1 N2 101.5(4) . . ?
N3 Cu1 I1 126.6(3) . . ?
N1 Cu1 I1 111.1(3) . . ?
N2 Cu1 I1 118.4(3) . . ?
N5 Cu2 N4 99.4(4) . . ?
N5 Cu2 N6 99.6(4) . . ?
N4 Cu2 N6 97.5(4) . . ?
N5 Cu2 I2 116.6(3) . . ?
N4 Cu2 I2 112.5(3) . . ?
N6 Cu2 I2 126.7(3) . . ?
O1 As1 C6 112.6(5) . . ?
O1 As1 C1 114.1(5) . . ?
C6 As1 C1 106.0(5) . . ?
O1 As1 C11 114.2(5) . . ?
C6 As1 C11 104.2(5) . . ?
C1 As1 C11 104.9(5) . . ?
O2 As2 C26 112.5(4) . . ?
O2 As2 C21 113.9(4) . . ?
C26 As2 C21 106.2(5) . . ?
O2 As2 C16 114.7(5) . . ?
C26 As2 C16 103.1(5) . . ?
C21 As2 C16 105.4(5) . . ?
C34 C33 H33A 109.5 . . ?
C34 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C34 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
N8 C34 C33 177(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 C1 C2 C3 -1(2) . . . . ?
As1 C1 C2 C3 -178.6(10) . . . . ?
C1 C2 C3 C4 1(2) . . . . ?
C2 C3 C4 C5 -1(2) . . . . ?
C3 C4 C5 N1 0(2) . . . . ?
N3 C11 C12 C13 0.2(18) . . . . ?
As1 C11 C12 C13 -179.4(9) . . . . ?
C11 C12 C13 C14 0.6(19) . . . . ?
C12 C13 C14 C15 0(2) . . . . ?
C13 C14 C15 N3 -2(2) . . . . ?
N2 C6 C7 C8 -2.5(18) . . . . ?
As1 C6 C7 C8 176.2(9) . . . . ?
C6 C7 C8 C9 -0.4(18) . . . . ?
C7 C8 C9 C10 2.6(18) . . . . ?
C8 C9 C10 N2 -2.0(19) . . . . ?
N6 C26 C27 C28 0.2(18) . . . . ?
As2 C26 C27 C28 177.9(9) . . . . ?
C26 C27 C28 C29 1.2(18) . . . . ?
C27 C28 C29 C30 -1.3(19) . . . . ?
C28 C29 C30 N6 0.0(19) . . . . ?
N4 C16 C17 C18 0.0(19) . . . . ?
As2 C16 C17 C18 -179.5(9) . . . . ?
C16 C17 C18 C19 -0.4(18) . . . . ?
C17 C18 C19 C20 1.3(18) . . . . ?
C18 C19 C20 N4 -2(2) . . . . ?
N5 C21 C22 C23 0.2(18) . . . . ?
As2 C21 C22 C23 -179.0(9) . . . . ?
C21 C22 C23 C24 -0.6(18) . . . . ?
C22 C23 C24 C25 0.5(19) . . . . ?
C23 C24 C25 N5 0.1(19) . . . . ?
C4 C5 N1 C1 0.1(18) . . . . ?
C4 C5 N1 Cu1 -177.6(10) . . . . ?
C2 C1 N1 C5 0.3(18) . . . . ?
As1 C1 N1 C5 178.0(9) . . . . ?
C2 C1 N1 Cu1 178.1(10) . . . . ?
As1 C1 N1 Cu1 -4.1(12) . . . . ?
C14 C15 N3 C11 2.8(19) . . . . ?
C14 C15 N3 Cu1 -179.1(10) . . . . ?
C12 C11 N3 C15 -1.9(18) . . . . ?
As1 C11 N3 C15 177.8(9) . . . . ?
C12 C11 N3 Cu1 179.8(9) . . . . ?
As1 C11 N3 Cu1 -0.5(11) . . . . ?
C9 C10 N2 C6 -0.7(17) . . . . ?
C9 C10 N2 Cu1 179.9(9) . . . . ?
C7 C6 N2 C10 3.0(17) . . . . ?
As1 C6 N2 C10 -175.7(8) . . . . ?
C7 C6 N2 Cu1 -177.5(9) . . . . ?
As1 C6 N2 Cu1 3.8(11) . . . . ?
C29 C30 N6 C26 1.3(17) . . . . ?
C29 C30 N6 Cu2 -177.9(9) . . . . ?
C27 C26 N6 C30 -1.4(17) . . . . ?
As2 C26 N6 C30 -179.2(8) . . . . ?
C27 C26 N6 Cu2 177.8(9) . . . . ?
As2 C26 N6 Cu2 0.0(11) . . . . ?
C19 C20 N4 C16 1.3(17) . . . . ?
C19 C20 N4 Cu2 179.7(10) . . . . ?
C17 C16 N4 C20 -0.3(17) . . . . ?
As2 C16 N4 C20 179.2(8) . . . . ?
C17 C16 N4 Cu2 -178.8(9) . . . . ?
As2 C16 N4 Cu2 0.6(11) . . . . ?
C22 C21 N5 C25 0.4(17) . . . . ?
As2 C21 N5 C25 179.7(8) . . . . ?
C22 C21 N5 Cu2 -176.1(9) . . . . ?
As2 C21 N5 Cu2 3.2(11) . . . . ?
C24 C25 N5 C21 -0.5(17) . . . . ?
C24 C25 N5 Cu2 175.6(9) . . . . ?

_refine_diff_density_max         2.330
_refine_diff_density_min         -1.379
_refine_diff_density_rms         0.167

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_tgn430
_database_code_depnum_ccdc_archive 'CCDC 1021445'
_audit_contact_author            'Joerg Sundermeyer'
_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
Iodo tris(2-pyridyl)methane copper(I)
;
_chemical_name_common            'C9, CuItpym'
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 Cu1 I1 N3'
_chemical_formula_sum            'C16 H13 Cu I N3'
_chemical_formula_weight         437.73

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'
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'

_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                   14.7528(4)
_cell_length_b                   13.4193(3)
_cell_length_c                   16.0010(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.266(2)
_cell_angle_gamma                90
_cell_volume                     3167.72(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    49953
_cell_measurement_theta_min      1.27
_cell_measurement_theta_max      27.22

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.836
_exptl_crystal_F_000             1696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.324
_shelx_estimated_absorpt_T_min   0.293
_shelx_estimated_absorpt_T_max   0.732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2865
_exptl_absorpt_correction_T_max  0.5605
_exptl_absorpt_process_details   
; 
R. H. Blessing, Acta Cryst. A 1995, 51, 33-38.
;

_exptl_special_details           ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   
;
sealed X-ray tube, 12 x 0.4 mm long-fine focus
;
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            47871
_diffrn_reflns_av_unetI/netI     0.0969
_diffrn_reflns_av_R_equivalents  0.1108
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.873
_diffrn_reflns_theta_max         26.746
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6720
_reflns_number_gt                5801
_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       
;
Stoe & Cie: X-AREA v1.56, Stoe & Cie GmbH, Darmstadt, Germany, 2011
;
_computing_cell_refinement       
;
Stoe & Cie: X-AREA v1.56, Stoe & Cie GmbH, Darmstadt, Germany, 2011
;
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    
;
SIR97 (A. Altomare, M. C. Burla, M. Camalli, G. Cascarano, C. Giacovazzo, 
A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, 
J. Appl. Crystallogr. 1999, 32, 115-119.)
;
_computing_structure_refinement  
;
SHELXL-2014 (G. Sheldrick, Acta Cryst. A 2008, 64, 112-122)
;
_computing_molecular_graphics    
;
K. Brandenburg, H. Putz: 
Diamond - Crystal and Molecular Structure Visualization v3.2i, 
Crystal Impact GbR, Bonn, Germany, 2012
;
_computing_publication_material  
;
WinGX publication routines (L. Farrugia, 
J. Appl. Crystallogr. 1999, 32, 837-838.)
;

_refine_special_details          
;
Platon/ADDSYM reports on an additional (Pseudo)symmetry element (C). 
This corresponds to a partial C-Superlattice which can be observed 
in the data. Solution and refinement with a C-centered lattice 
result in significantly increased R and R(int) values, though. 
The current solution has to be preferred.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0466P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6720
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0745
_refine_ls_wR_factor_gt          0.0705
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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 0.91129(2) 0.24043(2) 0.89724(2) 0.02605(6) Uani 1 1 d . . . . .
I2 I 0.09619(2) 0.24427(2) 0.59606(2) 0.02500(6) Uani 1 1 d . . . . .
Cu1 Cu 0.84551(2) 0.10017(2) 0.81808(2) 0.02487(8) Uani 1 1 d . . . . .
Cu2 Cu 0.15456(2) 0.11275(2) 0.69009(2) 0.02450(8) Uani 1 1 d . . . . .
N1 N 0.70925(13) 0.06532(14) 0.83831(11) 0.0224(4) Uani 1 1 d . . . . .
N3 N 0.82528(13) 0.08508(14) 0.69141(12) 0.0244(4) Uani 1 1 d . . . . .
N4 N 0.28909(13) 0.06994(14) 0.66233(11) 0.0217(4) Uani 1 1 d . . . . .
N6 N 0.18432(14) 0.10480(14) 0.81526(12) 0.0254(4) Uani 1 1 d . . . . .
N5 N 0.11333(14) -0.03504(14) 0.68880(12) 0.0267(4) Uani 1 1 d . . . . .
N2 N 0.88158(14) -0.04882(15) 0.82732(12) 0.0268(4) Uani 1 1 d . . . . .
C1 C 0.68022(15) -0.01638(16) 0.79709(13) 0.0211(4) Uani 1 1 d . . . . .
C17 C 0.31797(15) -0.01052(16) 0.70497(13) 0.0211(4) Uani 1 1 d . . . . .
C2 C 0.59465(16) -0.05684(17) 0.81044(14) 0.0242(5) Uani 1 1 d . . . . .
H2 H 0.5758 -0.1148 0.7811 0.029 Uiso 1 1 calc R U . . .
C21 C 0.34297(16) 0.10872(16) 0.60360(13) 0.0226(4) Uani 1 1 d . . . . .
H21 H 0.3226 0.1657 0.5737 0.027 Uiso 1 1 calc R U . . .
C18 C 0.40144(16) -0.05494(16) 0.68923(14) 0.0238(5) Uani 1 1 d . . . . .
H18 H 0.4202 -0.1121 0.7197 0.029 Uiso 1 1 calc R U . . .
C5 C 0.65304(16) 0.10924(16) 0.89264(13) 0.0227(4) Uani 1 1 d . . . . .
H5 H 0.6733 0.1673 0.9211 0.027 Uiso 1 1 calc R U . . .
C22 C 0.17024(16) -0.09713(17) 0.72902(14) 0.0252(5) Uani 1 1 d . . . . .
C19 C 0.45653(16) -0.01441(17) 0.62854(14) 0.0254(5) Uani 1 1 d . . . . .
H19 H 0.5139 -0.0434 0.6170 0.030 Uiso 1 1 calc R U . . .
C32 C 0.25380(16) -0.05304(16) 0.77046(13) 0.0226(4) Uani 1 1 d . . . . .
H32 H 0.2864 -0.1091 0.7987 0.027 Uiso 1 1 calc R U . . .
C24 C 0.0801(2) -0.23789(18) 0.68983(18) 0.0353(6) Uani 1 1 d . . . . .
H24 H 0.0688 -0.3076 0.6900 0.042 Uiso 1 1 calc R U . . .
C3 C 0.53757(17) -0.01124(17) 0.86708(14) 0.0273(5) Uani 1 1 d . . . . .
H3 H 0.4789 -0.0378 0.8772 0.033 Uiso 1 1 calc R U . . .
C7 C 0.83662(17) -0.21454(18) 0.79065(15) 0.0293(5) Uani 1 1 d . . . . .
H7 H 0.7960 -0.2577 0.7620 0.035 Uiso 1 1 calc R U . . .
C6 C 0.82521(16) -0.11184(16) 0.78744(14) 0.0249(5) Uani 1 1 d . . . . .
C11 C 0.78097(16) 0.00177(17) 0.66879(14) 0.0253(5) Uani 1 1 d . . . . .
C16 C 0.74687(15) -0.06643(16) 0.73801(13) 0.0223(4) Uani 1 1 d . . . . .
H16 H 0.7139 -0.1227 0.7104 0.027 Uiso 1 1 calc R U . . .
C20 C 0.42748(16) 0.06906(17) 0.58455(14) 0.0252(5) Uani 1 1 d . . . . .
H20 H 0.4643 0.0982 0.5426 0.030 Uiso 1 1 calc R U . . .
C27 C 0.23214(16) 0.02401(17) 0.83792(14) 0.0248(5) Uani 1 1 d . . . . .
C4 C 0.56666(16) 0.07383(17) 0.90918(14) 0.0250(5) Uani 1 1 d . . . . .
H4 H 0.5285 0.1067 0.9481 0.030 Uiso 1 1 calc R U . . .
C26 C 0.04041(17) -0.07262(19) 0.65014(15) 0.0295(5) Uani 1 1 d . . . . .
H26 H 0.0000 -0.0282 0.6226 0.035 Uiso 1 1 calc R U . . .
C15 C 0.85744(17) 0.14467(18) 0.63132(15) 0.0303(5) Uani 1 1 d . . . . .
H15 H 0.8885 0.2037 0.6472 0.036 Uiso 1 1 calc R U . . .
C8 C 0.9086(2) -0.25273(18) 0.83666(18) 0.0368(6) Uani 1 1 d . . . . .
H8 H 0.9176 -0.3227 0.8403 0.044 Uiso 1 1 calc R U . . .
C23 C 0.15562(17) -0.19946(17) 0.73091(15) 0.0297(5) Uani 1 1 d . . . . .
H23 H 0.1964 -0.2423 0.7597 0.036 Uiso 1 1 calc R U . . .
C10 C 0.95141(17) -0.0869(2) 0.87105(16) 0.0329(5) Uani 1 1 d . . . . .
H10 H 0.9916 -0.0425 0.8989 0.039 Uiso 1 1 calc R U . . .
C25 C 0.02138(18) -0.1739(2) 0.64868(16) 0.0340(5) Uani 1 1 d . . . . .
H25 H -0.0306 -0.1987 0.6202 0.041 Uiso 1 1 calc R U . . .
C31 C 0.16652(17) 0.17413(18) 0.87369(15) 0.0314(5) Uani 1 1 d . . . . .
H31 H 0.1312 0.2305 0.8583 0.038 Uiso 1 1 calc R U . . .
C12 C 0.7685(2) -0.0240(2) 0.58614(16) 0.0398(6) Uani 1 1 d . . . . .
H12 H 0.7367 -0.0832 0.5717 0.048 Uiso 1 1 calc R U . . .
C30 C 0.1974(2) 0.1667(2) 0.95498(16) 0.0413(6) Uani 1 1 d . . . . .
H30 H 0.1846 0.2176 0.9944 0.050 Uiso 1 1 calc R U . . .
C28 C 0.2639(2) 0.0107(2) 0.91865(15) 0.0370(6) Uani 1 1 d . . . . .
H28 H 0.2966 -0.0478 0.9333 0.044 Uiso 1 1 calc R U . . .
C14 C 0.8474(2) 0.1241(2) 0.54749(17) 0.0439(7) Uani 1 1 d . . . . .
H14 H 0.8705 0.1684 0.5064 0.053 Uiso 1 1 calc R U . . .
C9 C 0.96692(19) -0.1884(2) 0.87700(16) 0.0367(6) Uani 1 1 d . . . . .
H9 H 1.0169 -0.2132 0.9083 0.044 Uiso 1 1 calc R U . . .
C29 C 0.2473(2) 0.0840(2) 0.97803(16) 0.0456(7) Uani 1 1 d . . . . .
H29 H 0.2698 0.0774 1.0335 0.055 Uiso 1 1 calc R U . . .
C13 C 0.8030(2) 0.0374(3) 0.52436(17) 0.0543(9) Uani 1 1 d . . . . .
H13 H 0.7962 0.0203 0.4671 0.065 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 2.4652(3) . ?
I2 Cu2 2.4715(3) . ?
Cu1 N3 2.0574(19) . ?
Cu1 N2 2.074(2) . ?
Cu1 N1 2.0907(19) . ?
Cu2 N6 2.051(2) . ?
Cu2 N5 2.074(2) . ?
Cu2 N4 2.1153(19) . ?
N1 C5 1.341(3) . ?
N1 C1 1.348(3) . ?
N3 C15 1.339(3) . ?
N3 C11 1.344(3) . ?
N4 C21 1.339(3) . ?
N4 C17 1.345(3) . ?
N6 C27 1.342(3) . ?
N6 C31 1.346(3) . ?
N5 C26 1.337(3) . ?
N5 C22 1.345(3) . ?
N2 C10 1.344(3) . ?
N2 C6 1.345(3) . ?
C1 C2 1.392(3) . ?
C1 C16 1.523(3) . ?
C17 C18 1.392(3) . ?
C17 C32 1.526(3) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9500 . ?
C21 C20 1.391(3) . ?
C21 H21 0.9500 . ?
C18 C19 1.381(3) . ?
C18 H18 0.9500 . ?
C5 C4 1.387(3) . ?
C5 H5 0.9500 . ?
C22 C23 1.390(3) . ?
C22 C32 1.517(3) . ?
C19 C20 1.390(3) . ?
C19 H19 0.9500 . ?
C32 C27 1.530(3) . ?
C32 H32 1.0000 . ?
C24 C25 1.384(4) . ?
C24 C23 1.391(4) . ?
C24 H24 0.9500 . ?
C3 C4 1.392(3) . ?
C3 H3 0.9500 . ?
C7 C8 1.387(4) . ?
C7 C6 1.389(3) . ?
C7 H7 0.9500 . ?
C6 C16 1.524(3) . ?
C11 C12 1.379(3) . ?
C11 C16 1.524(3) . ?
C16 H16 1.0000 . ?
C20 H20 0.9500 . ?
C27 C28 1.384(3) . ?
C4 H4 0.9500 . ?
C26 C25 1.388(4) . ?
C26 H26 0.9500 . ?
C15 C14 1.377(3) . ?
C15 H15 0.9500 . ?
C8 C9 1.377(4) . ?
C8 H8 0.9500 . ?
C23 H23 0.9500 . ?
C10 C9 1.384(4) . ?
C10 H10 0.9500 . ?
C25 H25 0.9500 . ?
C31 C30 1.380(3) . ?
C31 H31 0.9500 . ?
C12 C13 1.385(4) . ?
C12 H12 0.9500 . ?
C30 C29 1.380(4) . ?
C30 H30 0.9500 . ?
C28 C29 1.391(4) . ?
C28 H28 0.9500 . ?
C14 C13 1.385(4) . ?
C14 H14 0.9500 . ?
C9 H9 0.9500 . ?
C29 H29 0.9500 . ?
C13 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Cu1 N2 90.65(8) . . ?
N3 Cu1 N1 89.73(7) . . ?
N2 Cu1 N1 91.14(8) . . ?
N3 Cu1 I1 129.52(5) . . ?
N2 Cu1 I1 126.81(6) . . ?
N1 Cu1 I1 117.89(5) . . ?
N6 Cu2 N5 91.23(8) . . ?
N6 Cu2 N4 89.67(7) . . ?
N5 Cu2 N4 90.78(8) . . ?
N6 Cu2 I2 134.75(5) . . ?
N5 Cu2 I2 125.12(6) . . ?
N4 Cu2 I2 113.00(5) . . ?
C5 N1 C1 118.6(2) . . ?
C5 N1 Cu1 126.88(15) . . ?
C1 N1 Cu1 114.18(15) . . ?
C15 N3 C11 118.5(2) . . ?
C15 N3 Cu1 126.75(16) . . ?
C11 N3 Cu1 114.54(15) . . ?
C21 N4 C17 118.70(19) . . ?
C21 N4 Cu2 127.05(15) . . ?
C17 N4 Cu2 114.00(15) . . ?
C27 N6 C31 118.3(2) . . ?
C27 N6 Cu2 114.55(15) . . ?
C31 N6 Cu2 126.93(16) . . ?
C26 N5 C22 119.1(2) . . ?
C26 N5 Cu2 126.89(16) . . ?
C22 N5 Cu2 113.91(16) . . ?
C10 N2 C6 118.6(2) . . ?
C10 N2 Cu1 126.84(17) . . ?
C6 N2 Cu1 114.49(16) . . ?
N1 C1 C2 121.9(2) . . ?
N1 C1 C16 117.24(19) . . ?
C2 C1 C16 120.79(19) . . ?
N4 C17 C18 122.0(2) . . ?
N4 C17 C32 116.88(19) . . ?
C18 C17 C32 121.08(19) . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
N4 C21 C20 122.7(2) . . ?
N4 C21 H21 118.6 . . ?
C20 C21 H21 118.6 . . ?
C19 C18 C17 118.9(2) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
N1 C5 C4 123.0(2) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
N5 C22 C23 121.7(2) . . ?
N5 C22 C32 118.15(19) . . ?
C23 C22 C32 120.1(2) . . ?
C18 C19 C20 119.5(2) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C22 C32 C17 110.56(17) . . ?
C22 C32 C27 113.58(19) . . ?
C17 C32 C27 111.36(18) . . ?
C22 C32 H32 107.0 . . ?
C17 C32 H32 107.0 . . ?
C27 C32 H32 107.0 . . ?
C25 C24 C23 119.5(2) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C2 C3 C4 119.5(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C8 C7 C6 118.6(2) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
N2 C6 C7 122.1(2) . . ?
N2 C6 C16 117.41(19) . . ?
C7 C6 C16 120.5(2) . . ?
N3 C11 C12 122.0(2) . . ?
N3 C11 C16 117.75(19) . . ?
C12 C11 C16 120.2(2) . . ?
C1 C16 C11 113.73(18) . . ?
C1 C16 C6 110.14(17) . . ?
C11 C16 C6 111.41(19) . . ?
C1 C16 H16 107.1 . . ?
C11 C16 H16 107.1 . . ?
C6 C16 H16 107.1 . . ?
C19 C20 C21 118.2(2) . . ?
C19 C20 H20 120.9 . . ?
C21 C20 H20 120.9 . . ?
N6 C27 C28 122.1(2) . . ?
N6 C27 C32 117.82(19) . . ?
C28 C27 C32 120.0(2) . . ?
C5 C4 C3 118.0(2) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
N5 C26 C25 122.6(2) . . ?
N5 C26 H26 118.7 . . ?
C25 C26 H26 118.7 . . ?
N3 C15 C14 122.9(2) . . ?
N3 C15 H15 118.6 . . ?
C14 C15 H15 118.6 . . ?
C9 C8 C7 119.5(2) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C22 C23 C24 118.7(2) . . ?
C22 C23 H23 120.7 . . ?
C24 C23 H23 120.7 . . ?
N2 C10 C9 122.4(2) . . ?
N2 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
C24 C25 C26 118.3(2) . . ?
C24 C25 H25 120.9 . . ?
C26 C25 H25 120.9 . . ?
N6 C31 C30 122.7(2) . . ?
N6 C31 H31 118.7 . . ?
C30 C31 H31 118.7 . . ?
C11 C12 C13 119.2(2) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C29 C30 C31 118.9(2) . . ?
C29 C30 H30 120.6 . . ?
C31 C30 H30 120.6 . . ?
C27 C28 C29 119.1(2) . . ?
C27 C28 H28 120.5 . . ?
C29 C28 H28 120.5 . . ?
C15 C14 C13 118.5(2) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C8 C9 C10 118.8(2) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C30 C29 C28 118.8(2) . . ?
C30 C29 H29 120.6 . . ?
C28 C29 H29 120.6 . . ?
C12 C13 C14 118.9(2) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?

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
C5 N1 C1 C2 -1.1(3) . . . . ?
Cu1 N1 C1 C2 172.70(16) . . . . ?
C5 N1 C1 C16 -178.01(19) . . . . ?
Cu1 N1 C1 C16 -4.2(2) . . . . ?
C21 N4 C17 C18 -0.7(3) . . . . ?
Cu2 N4 C17 C18 173.93(16) . . . . ?
C21 N4 C17 C32 -179.18(19) . . . . ?
Cu2 N4 C17 C32 -4.6(2) . . . . ?
N1 C1 C2 C3 0.6(3) . . . . ?
C16 C1 C2 C3 177.5(2) . . . . ?
C17 N4 C21 C20 0.3(3) . . . . ?
Cu2 N4 C21 C20 -173.54(16) . . . . ?
N4 C17 C18 C19 0.7(3) . . . . ?
C32 C17 C18 C19 179.1(2) . . . . ?
C1 N1 C5 C4 0.8(3) . . . . ?
Cu1 N1 C5 C4 -172.11(16) . . . . ?
C26 N5 C22 C23 0.5(3) . . . . ?
Cu2 N5 C22 C23 -176.79(18) . . . . ?
C26 N5 C22 C32 178.4(2) . . . . ?
Cu2 N5 C22 C32 1.1(3) . . . . ?
C17 C18 C19 C20 -0.3(3) . . . . ?
N5 C22 C32 C17 -65.8(3) . . . . ?
C23 C22 C32 C17 112.1(2) . . . . ?
N5 C22 C32 C27 60.2(3) . . . . ?
C23 C22 C32 C27 -121.9(2) . . . . ?
N4 C17 C32 C22 67.3(2) . . . . ?
C18 C17 C32 C22 -111.2(2) . . . . ?
N4 C17 C32 C27 -60.0(3) . . . . ?
C18 C17 C32 C27 121.5(2) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C10 N2 C6 C7 0.5(3) . . . . ?
Cu1 N2 C6 C7 -176.71(18) . . . . ?
C10 N2 C6 C16 -179.7(2) . . . . ?
Cu1 N2 C6 C16 3.1(3) . . . . ?
C8 C7 C6 N2 0.0(4) . . . . ?
C8 C7 C6 C16 -179.7(2) . . . . ?
C15 N3 C11 C12 0.5(4) . . . . ?
Cu1 N3 C11 C12 -174.4(2) . . . . ?
C15 N3 C11 C16 178.5(2) . . . . ?
Cu1 N3 C11 C16 3.6(3) . . . . ?
N1 C1 C16 C11 -58.8(3) . . . . ?
C2 C1 C16 C11 124.3(2) . . . . ?
N1 C1 C16 C6 67.1(2) . . . . ?
C2 C1 C16 C6 -109.9(2) . . . . ?
N3 C11 C16 C1 59.9(3) . . . . ?
C12 C11 C16 C1 -122.1(3) . . . . ?
N3 C11 C16 C6 -65.3(3) . . . . ?
C12 C11 C16 C6 112.7(3) . . . . ?
N2 C6 C16 C1 -66.6(3) . . . . ?
C7 C6 C16 C1 113.2(2) . . . . ?
N2 C6 C16 C11 60.6(3) . . . . ?
C7 C6 C16 C11 -119.7(2) . . . . ?
C18 C19 C20 C21 -0.1(3) . . . . ?
N4 C21 C20 C19 0.1(3) . . . . ?
C31 N6 C27 C28 -0.5(4) . . . . ?
Cu2 N6 C27 C28 175.0(2) . . . . ?
C31 N6 C27 C32 -178.6(2) . . . . ?
Cu2 N6 C27 C32 -3.1(3) . . . . ?
C22 C32 C27 N6 -59.2(3) . . . . ?
C17 C32 C27 N6 66.4(3) . . . . ?
C22 C32 C27 C28 122.6(2) . . . . ?
C17 C32 C27 C28 -111.8(3) . . . . ?
N1 C5 C4 C3 0.0(3) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C22 N5 C26 C25 -0.9(3) . . . . ?
Cu2 N5 C26 C25 175.97(18) . . . . ?
C11 N3 C15 C14 -0.3(4) . . . . ?
Cu1 N3 C15 C14 174.0(2) . . . . ?
C6 C7 C8 C9 -0.6(4) . . . . ?
N5 C22 C23 C24 0.1(4) . . . . ?
C32 C22 C23 C24 -177.8(2) . . . . ?
C25 C24 C23 C22 -0.3(4) . . . . ?
C6 N2 C10 C9 -0.5(4) . . . . ?
Cu1 N2 C10 C9 176.33(19) . . . . ?
C23 C24 C25 C26 -0.1(4) . . . . ?
N5 C26 C25 C24 0.7(4) . . . . ?
C27 N6 C31 C30 1.8(4) . . . . ?
Cu2 N6 C31 C30 -173.1(2) . . . . ?
N3 C11 C12 C13 0.3(4) . . . . ?
C16 C11 C12 C13 -177.7(3) . . . . ?
N6 C31 C30 C29 -1.2(4) . . . . ?
N6 C27 C28 C29 -1.2(4) . . . . ?
C32 C27 C28 C29 176.8(3) . . . . ?
N3 C15 C14 C13 -0.7(5) . . . . ?
C7 C8 C9 C10 0.6(4) . . . . ?
N2 C10 C9 C8 -0.1(4) . . . . ?
C31 C30 C29 C28 -0.6(5) . . . . ?
C27 C28 C29 C30 1.7(5) . . . . ?
C11 C12 C13 C14 -1.3(5) . . . . ?
C15 C14 C13 C12 1.5(5) . . . . ?

_refine_diff_density_max         0.534
_refine_diff_density_min         -0.906
_refine_diff_density_rms         0.106

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_tgv109

_database_code_depnum_ccdc_archive 'CCDC 1021446'
_audit_contact_author            'Joerg Sundermeyer'
_audit_creation_method           SHELXL-2014
_chemical_name_systematic        Tris(2-pyridyl)arsine
_chemical_name_common            tpyas
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 As1 N3'
_chemical_formula_sum            'C15 H12 As N3'
_chemical_formula_weight         309.20

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'
As As 0.0499 2.0058 '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                   9.1529(9)
_cell_length_b                   9.1102(6)
_cell_length_c                   16.0342(16)
_cell_angle_alpha                90
_cell_angle_beta                 100.982(8)
_cell_angle_gamma                90
_cell_volume                     1312.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4379
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      2.25

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    2.578
_shelx_estimated_absorpt_T_min   0.589
_shelx_estimated_absorpt_T_max   0.601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4643
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   
; 
R. H. Blessing, Acta Cryst. A 1995, 51, 33-38.
;

_exptl_special_details           ?


_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
;
sealed X-ray tube, 12 x 0.4 mm long-fine focus
;
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            8036
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.267
_diffrn_reflns_theta_max         26.699
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2763
_reflns_number_gt                2318
_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       
;
Stoe & Cie: X-AREA v1.56, Stoe & Cie GmbH, Darmstadt, Germany, 2011
;
_computing_cell_refinement       
;
Stoe & Cie: X-AREA v1.56, Stoe & Cie GmbH, Darmstadt, Germany, 2011
;
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    
;
SHELXS-97 (G. Sheldrick, Acta Cryst. A 2008, 64, 112-122)
;
_computing_structure_refinement  
;
SHELXL-2014 (G. Sheldrick, Acta Cryst. A 2008, 64, 112-122)
;
_computing_molecular_graphics    
;
K. Brandenburg, H. Putz: 
Diamond - Crystal and Molecular Structure Visualization v3.2i, 
Crystal Impact GbR, Bonn, Germany, 2012
;
_computing_publication_material  
;
WinGX publication routines (L. Farrugia, 
J. Appl. Crystallogr. 1999, 32, 837-838.)
;
_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)+(0.0404P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2763
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0666
_refine_ls_wR_factor_gt          0.0645
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_restrained_S_all      0.965
_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
As1 As 0.90051(2) 0.79053(2) 0.12896(2) 0.02849(8) Uani 1 1 d . . . . .
C1 C 0.7589(2) 0.7035(2) 0.19268(13) 0.0289(4) Uani 1 1 d . . . . .
N1 N 0.6212(2) 0.75836(19) 0.18405(12) 0.0315(4) Uani 1 1 d . . . . .
N2 N 0.82781(19) 1.07315(18) 0.16510(11) 0.0306(4) Uani 1 1 d . . . . .
C5 C 0.5319(2) 0.6975(2) 0.23207(15) 0.0338(5) Uani 1 1 d . . . . .
H5 H 0.4340 0.7358 0.2270 0.041 Uiso 1 1 calc R U . . .
C7 C 0.7048(2) 1.0106(2) 0.02369(14) 0.0332(5) Uani 1 1 d . . . . .
H7 H 0.6852 0.9395 -0.0204 0.040 Uiso 1 1 calc R U . . .
C11 C 0.8399(2) 0.6852(2) 0.02051(14) 0.0296(4) Uani 1 1 d . . . . .
N3 N 0.7109(2) 0.6115(2) 0.00469(12) 0.0349(4) Uani 1 1 d . . . . .
C6 C 0.7959(2) 0.9773(2) 0.10034(13) 0.0291(4) Uani 1 1 d . . . . .
C10 C 0.7667(2) 1.2074(2) 0.15280(15) 0.0341(5) Uani 1 1 d . . . . .
H10 H 0.7875 1.2763 0.1980 0.041 Uiso 1 1 calc R U . . .
C12 C 0.9393(3) 0.6891(2) -0.03558(14) 0.0342(5) Uani 1 1 d . . . . .
H12 H 1.0304 0.7416 -0.0216 0.041 Uiso 1 1 calc R U . . .
C9 C 0.6750(3) 1.2509(2) 0.07796(16) 0.0363(5) Uani 1 1 d . . . . .
H9 H 0.6355 1.3476 0.0718 0.044 Uiso 1 1 calc R U . . .
C2 C 0.8110(2) 0.5896(2) 0.24805(13) 0.0303(4) Uani 1 1 d . . . . .
H2 H 0.9099 0.5545 0.2527 0.036 Uiso 1 1 calc R U . . .
C15 C 0.6783(3) 0.5403(2) -0.07010(14) 0.0366(5) Uani 1 1 d . . . . .
H15 H 0.5871 0.4879 -0.0827 0.044 Uiso 1 1 calc R U . . .
C14 C 0.7693(3) 0.5387(2) -0.12984(14) 0.0357(5) Uani 1 1 d . . . . .
H14 H 0.7411 0.4867 -0.1818 0.043 Uiso 1 1 calc R U . . .
C4 C 0.5729(2) 0.5826(2) 0.28844(14) 0.0335(5) Uani 1 1 d . . . . .
H4 H 0.5050 0.5429 0.3205 0.040 Uiso 1 1 calc R U . . .
C13 C 0.9023(3) 0.6148(2) -0.11195(14) 0.0375(5) Uani 1 1 d . . . . .
H13 H 0.9673 0.6161 -0.1516 0.045 Uiso 1 1 calc R U . . .
C3 C 0.7160(2) 0.5278(2) 0.29652(14) 0.0331(5) Uani 1 1 d . . . . .
H3 H 0.7488 0.4493 0.3345 0.040 Uiso 1 1 calc R U . . .
C8 C 0.6422(3) 1.1500(2) 0.01209(15) 0.0375(5) Uani 1 1 d . . . . .
H8 H 0.5784 1.1756 -0.0398 0.045 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
As1 C6 1.963(2) . ?
As1 C1 1.964(2) . ?
As1 C11 1.971(2) . ?
C1 N1 1.339(3) . ?
C1 C2 1.389(3) . ?
N1 C5 1.345(3) . ?
N2 C10 1.344(3) . ?
N2 C6 1.346(3) . ?
C5 C4 1.387(3) . ?
C5 H5 0.9500 . ?
C7 C6 1.381(3) . ?
C7 C8 1.391(3) . ?
C7 H7 0.9500 . ?
C11 N3 1.340(3) . ?
C11 C12 1.397(3) . ?
N3 C15 1.346(3) . ?
C10 C9 1.385(3) . ?
C10 H10 0.9500 . ?
C12 C13 1.384(3) . ?
C12 H12 0.9500 . ?
C9 C8 1.389(3) . ?
C9 H9 0.9500 . ?
C2 C3 1.391(3) . ?
C2 H2 0.9500 . ?
C15 C14 1.384(3) . ?
C15 H15 0.9500 . ?
C14 C13 1.382(3) . ?
C14 H14 0.9500 . ?
C4 C3 1.385(3) . ?
C4 H4 0.9500 . ?
C13 H13 0.9500 . ?
C3 H3 0.9500 . ?
C8 H8 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 As1 C1 97.52(8) . . ?
C6 As1 C11 99.96(8) . . ?
C1 As1 C11 99.19(8) . . ?
N1 C1 C2 123.12(19) . . ?
N1 C1 As1 119.81(15) . . ?
C2 C1 As1 117.01(15) . . ?
C1 N1 C5 116.76(18) . . ?
C10 N2 C6 117.04(18) . . ?
N1 C5 C4 124.4(2) . . ?
N1 C5 H5 117.8 . . ?
C4 C5 H5 117.8 . . ?
C6 C7 C8 118.9(2) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
N3 C11 C12 123.3(2) . . ?
N3 C11 As1 120.07(15) . . ?
C12 C11 As1 116.58(16) . . ?
C11 N3 C15 116.63(19) . . ?
N2 C6 C7 123.32(19) . . ?
N2 C6 As1 110.96(15) . . ?
C7 C6 As1 125.69(15) . . ?
N2 C10 C9 123.7(2) . . ?
N2 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
C13 C12 C11 118.5(2) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C10 C9 C8 118.5(2) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C1 C2 C3 119.0(2) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
N3 C15 C14 124.1(2) . . ?
N3 C15 H15 117.9 . . ?
C14 C15 H15 117.9 . . ?
C13 C14 C15 118.2(2) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 H14 120.9 . . ?
C3 C4 C5 117.86(19) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
C14 C13 C12 119.1(2) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C4 C3 C2 118.83(19) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C9 C8 C7 118.6(2) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?

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
C2 C1 N1 C5 -0.2(3) . . . . ?
As1 C1 N1 C5 -177.39(15) . . . . ?
C1 N1 C5 C4 -0.5(3) . . . . ?
C12 C11 N3 C15 -0.9(3) . . . . ?
As1 C11 N3 C15 -178.94(16) . . . . ?
C10 N2 C6 C7 -0.1(3) . . . . ?
C10 N2 C6 As1 178.06(14) . . . . ?
C8 C7 C6 N2 0.0(3) . . . . ?
C8 C7 C6 As1 -177.90(16) . . . . ?
C6 N2 C10 C9 -0.4(3) . . . . ?
N3 C11 C12 C13 0.9(3) . . . . ?
As1 C11 C12 C13 179.07(16) . . . . ?
N2 C10 C9 C8 1.0(3) . . . . ?
N1 C1 C2 C3 0.7(3) . . . . ?
As1 C1 C2 C3 177.96(15) . . . . ?
C11 N3 C15 C14 0.4(3) . . . . ?
N3 C15 C14 C13 0.0(4) . . . . ?
N1 C5 C4 C3 0.7(3) . . . . ?
C15 C14 C13 C12 0.1(3) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
C5 C4 C3 C2 -0.1(3) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C10 C9 C8 C7 -1.0(3) . . . . ?
C6 C7 C8 C9 0.6(3) . . . . ?

_refine_diff_density_max         0.464
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.058

_shelxl_version_number           2014-3

