# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1560854'
_audit_update_record             
;
2017-07-07 deposited with the CCDC.
2017-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
1,8-di(iso-pentyl)-3,6,10,13-tetraphenyl-1,8-diaza-3,6,10,13-tetraphosphacyclotetradecane
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H58 N2 P4'
_chemical_formula_weight         714.78

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'

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

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

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

_cell_length_a                   5.623(5)
_cell_length_b                   13.319(11)
_cell_length_c                   14.842(13)
_cell_angle_alpha                112.941(10)
_cell_angle_beta                 95.282(11)
_cell_angle_gamma                96.975(11)
_cell_volume                     1004.2(15)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1558
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      22.35
_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.219
_shelx_estimated_absorpt_T_min   0.919
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.879
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8329
_diffrn_reflns_av_unetI/netI     0.0960
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.507
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             3873
_reflns_number_gt                2293
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0928P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3873
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0643
_refine_ls_wR_factor_ref         0.1827
_refine_ls_wR_factor_gt          0.1526
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_restrained_S_all      0.975
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.27664(16) 0.24895(8) 0.42538(7) 0.0430(3) Uani 1 1 d . . . . .
P2 P 0.51334(16) 0.47992(7) 0.64087(7) 0.0415(3) Uani 1 1 d . . . . .
C13 C -0.0713(10) -0.1159(4) 0.3260(4) 0.0769(14) Uani 1 1 d . . . . .
H13 H -0.1363 -0.1902 0.3060 0.092 Uiso 1 1 calc R U . . .
C14 C 0.1505(12) -0.0739(4) 0.3793(5) 0.116(2) Uani 1 1 d . . . . .
H14 H 0.2384 -0.1191 0.3983 0.140 Uiso 1 1 calc R U . . .
C15 C 0.2498(9) 0.0353(4) 0.4063(4) 0.0843(16) Uani 1 1 d . . . . .
H15 H 0.4062 0.0616 0.4413 0.101 Uiso 1 1 calc R U . . .
C10 C 0.1280(7) 0.1048(3) 0.3836(3) 0.0470(9) Uani 1 1 d . . . . .
C2 C 0.1295(6) 0.2999(3) 0.3372(3) 0.0417(8) Uani 1 1 d . . . . .
H2A H -0.0276 0.2530 0.3083 0.050 Uiso 1 1 calc R U . . .
H2B H 0.0993 0.3735 0.3761 0.050 Uiso 1 1 calc R U . . .
N1 N 0.2495(5) 0.3061(2) 0.2555(2) 0.0407(7) Uani 1 1 d . . . . .
C1 C 0.4928(6) 0.3702(3) 0.2909(3) 0.0461(9) Uani 1 1 d . . . . .
H1A H 0.5789 0.3599 0.2351 0.055 Uiso 1 1 calc R U . . .
H1B H 0.5797 0.3436 0.3343 0.055 Uiso 1 1 calc R U . . .
C4 C 0.1921(6) 0.4395(3) 0.5834(3) 0.0428(9) Uani 1 1 d . . . . .
H4A H 0.0928 0.4682 0.6347 0.051 Uiso 1 1 calc R U . . .
H4B H 0.1665 0.4741 0.5375 0.051 Uiso 1 1 calc R U . . .
C3 C 0.1062(6) 0.3154(3) 0.5283(3) 0.0450(9) Uani 1 1 d . . . . .
H3A H -0.0643 0.3020 0.5018 0.054 Uiso 1 1 calc R U . . .
H3B H 0.1222 0.2810 0.5749 0.054 Uiso 1 1 calc R U . . .
C19 C 0.5082(10) 0.3479(4) 0.8850(3) 0.0745(13) Uani 1 1 d . . . . .
H19 H 0.5095 0.3202 0.9337 0.089 Uiso 1 1 calc R U . . .
C20 C 0.3477(8) 0.4131(4) 0.8790(3) 0.0688(12) Uani 1 1 d . . . . .
H20 H 0.2383 0.4304 0.9239 0.083 Uiso 1 1 calc R U . . .
C21 C 0.3436(7) 0.4545(3) 0.8076(3) 0.0545(10) Uani 1 1 d . . . . .
H21 H 0.2317 0.4995 0.8045 0.065 Uiso 1 1 calc R U . . .
C16 C 0.5059(6) 0.4295(3) 0.7393(3) 0.0426(8) Uani 1 1 d . . . . .
C17 C 0.6664(7) 0.3631(3) 0.7471(3) 0.0566(10) Uani 1 1 d . . . . .
H17 H 0.7765 0.3449 0.7027 0.068 Uiso 1 1 calc R U . . .
C18 C 0.6689(8) 0.3224(4) 0.8193(4) 0.0759(13) Uani 1 1 d . . . . .
H18 H 0.7803 0.2775 0.8233 0.091 Uiso 1 1 calc R U . . .
C5 C 0.2249(7) 0.2012(3) 0.1682(3) 0.0477(9) Uani 1 1 d . . . . .
H5 H 0.0625 0.1604 0.1616 0.057 Uiso 1 1 calc R U . . .
C6 C 0.2317(8) 0.2244(4) 0.0759(3) 0.0630(11) Uani 1 1 d . . . . .
H6A H 0.3888 0.2672 0.0813 0.076 Uiso 1 1 calc R U . . .
H6B H 0.2159 0.1546 0.0190 0.076 Uiso 1 1 calc R U . . .
C8 C 0.0397(9) 0.2853(4) 0.0578(3) 0.0816(14) Uani 1 1 d . . . . .
H8A H -0.1158 0.2483 0.0601 0.122 Uiso 1 1 calc R U . . .
H8B H 0.0412 0.2872 -0.0061 0.122 Uiso 1 1 calc R U . . .
H8C H 0.0701 0.3595 0.1079 0.122 Uiso 1 1 calc R U . . .
C7 C 0.4026(7) 0.1268(3) 0.1758(3) 0.0577(11) Uani 1 1 d . . . . .
H7A H 0.4334 0.1352 0.2440 0.069 Uiso 1 1 calc R U . . .
H7B H 0.5549 0.1508 0.1584 0.069 Uiso 1 1 calc R U . . .
C9 C 0.3141(10) 0.0047(4) 0.1094(4) 0.0926(16) Uani 1 1 d . . . . .
H9A H 0.1654 -0.0204 0.1272 0.139 Uiso 1 1 calc R U . . .
H9B H 0.4343 -0.0377 0.1177 0.139 Uiso 1 1 calc R U . . .
H9C H 0.2870 -0.0048 0.0415 0.139 Uiso 1 1 calc R U . . .
C12 C -0.1953(10) -0.0488(4) 0.3026(4) 0.102(2) Uani 1 1 d . . . . .
H12 H -0.3493 -0.0764 0.2655 0.122 Uiso 1 1 calc R U . . .
C11 C -0.0997(9) 0.0608(4) 0.3323(4) 0.0955(19) Uani 1 1 d . . . . .
H11 H -0.1933 0.1065 0.3169 0.115 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
P1 C10 1.832(4) . ?
P1 C3 1.859(4) . ?
P1 C2 1.867(4) . ?
P2 C16 1.833(4) . ?
P2 C4 1.844(4) . ?
P2 C1 1.860(4) 2_666 ?
C13 C12 1.325(7) . ?
C13 C14 1.341(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(6) . ?
C14 H14 0.9300 . ?
C15 C10 1.338(6) . ?
C15 H15 0.9300 . ?
C10 C11 1.361(6) . ?
C2 N1 1.467(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
N1 C1 1.453(4) . ?
N1 C5 1.470(4) . ?
C1 P2 1.860(4) 2_666 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C4 C3 1.520(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C19 C20 1.347(6) . ?
C19 C18 1.364(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.372(6) . ?
C20 H20 0.9300 . ?
C21 C16 1.397(5) . ?
C21 H21 0.9300 . ?
C16 C17 1.365(5) . ?
C17 C18 1.375(6) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C5 C7 1.517(5) . ?
C5 C6 1.520(5) . ?
C5 H5 0.9800 . ?
C6 C8 1.491(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C7 C9 1.526(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C12 C11 1.370(6) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 P1 C3 99.45(16) . . ?
C10 P1 C2 105.04(17) . . ?
C3 P1 C2 96.43(17) . . ?
C16 P2 C4 100.85(16) . . ?
C16 P2 C1 102.12(17) . 2_666 ?
C4 P2 C1 96.68(16) . 2_666 ?
C12 C13 C14 118.2(4) . . ?
C12 C13 H13 120.9 . . ?
C14 C13 H13 120.9 . . ?
C13 C14 C15 120.9(5) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C10 C15 C14 121.9(5) . . ?
C10 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C15 C10 C11 115.9(4) . . ?
C15 C10 P1 118.1(3) . . ?
C11 C10 P1 126.0(3) . . ?
N1 C2 P1 120.5(2) . . ?
N1 C2 H2A 107.2 . . ?
P1 C2 H2A 107.2 . . ?
N1 C2 H2B 107.2 . . ?
P1 C2 H2B 107.2 . . ?
H2A C2 H2B 106.8 . . ?
C1 N1 C2 111.5(3) . . ?
C1 N1 C5 115.8(3) . . ?
C2 N1 C5 115.4(3) . . ?
N1 C1 P2 111.5(2) . 2_666 ?
N1 C1 H1A 109.3 . . ?
P2 C1 H1A 109.3 2_666 . ?
N1 C1 H1B 109.3 . . ?
P2 C1 H1B 109.3 2_666 . ?
H1A C1 H1B 108.0 . . ?
C3 C4 P2 114.7(2) . . ?
C3 C4 H4A 108.6 . . ?
P2 C4 H4A 108.6 . . ?
C3 C4 H4B 108.6 . . ?
P2 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C4 C3 P1 113.5(2) . . ?
C4 C3 H3A 108.9 . . ?
P1 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
P1 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C20 C19 C18 119.8(4) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 120.8(4) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C20 C21 C16 120.6(4) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
C17 C16 C21 117.3(4) . . ?
C17 C16 P2 118.9(3) . . ?
C21 C16 P2 123.8(3) . . ?
C16 C17 C18 121.5(4) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C19 C18 C17 120.1(4) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
N1 C5 C7 114.8(3) . . ?
N1 C5 C6 109.5(3) . . ?
C7 C5 C6 112.3(3) . . ?
N1 C5 H5 106.6 . . ?
C7 C5 H5 106.6 . . ?
C6 C5 H5 106.6 . . ?
C8 C6 C5 114.6(3) . . ?
C8 C6 H6A 108.6 . . ?
C5 C6 H6A 108.6 . . ?
C8 C6 H6B 108.6 . . ?
C5 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C7 C9 113.6(4) . . ?
C5 C7 H7A 108.8 . . ?
C9 C7 H7A 108.8 . . ?
C5 C7 H7B 108.8 . . ?
C9 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C13 C12 C11 120.9(5) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C10 C11 C12 122.1(5) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 C13 C14 C15 -2.0(10) . . . . ?
C13 C14 C15 C10 2.2(10) . . . . ?
C14 C15 C10 C11 0.0(8) . . . . ?
C14 C15 C10 P1 178.9(5) . . . . ?
C3 P1 C10 C15 -105.6(4) . . . . ?
C2 P1 C10 C15 155.1(4) . . . . ?
C3 P1 C10 C11 73.2(4) . . . . ?
C2 P1 C10 C11 -26.1(5) . . . . ?
C10 P1 C2 N1 -100.2(3) . . . . ?
C3 P1 C2 N1 158.2(3) . . . . ?
P1 C2 N1 C1 -54.2(4) . . . . ?
P1 C2 N1 C5 80.6(3) . . . . ?
C2 N1 C1 P2 -71.0(3) . . . 2_666 ?
C5 N1 C1 P2 154.4(2) . . . 2_666 ?
C16 P2 C4 C3 -68.9(3) . . . . ?
C1 P2 C4 C3 -172.6(2) 2_666 . . . ?
P2 C4 C3 P1 -59.6(3) . . . . ?
C10 P1 C3 C4 178.1(3) . . . . ?
C2 P1 C3 C4 -75.4(3) . . . . ?
C18 C19 C20 C21 0.0(8) . . . . ?
C19 C20 C21 C16 0.1(7) . . . . ?
C20 C21 C16 C17 0.0(6) . . . . ?
C20 C21 C16 P2 179.6(3) . . . . ?
C4 P2 C16 C17 128.1(3) . . . . ?
C1 P2 C16 C17 -132.5(3) 2_666 . . . ?
C4 P2 C16 C21 -51.5(4) . . . . ?
C1 P2 C16 C21 47.8(3) 2_666 . . . ?
C21 C16 C17 C18 -0.1(6) . . . . ?
P2 C16 C17 C18 -179.8(3) . . . . ?
C20 C19 C18 C17 -0.2(8) . . . . ?
C16 C17 C18 C19 0.2(7) . . . . ?
C1 N1 C5 C7 50.5(4) . . . . ?
C2 N1 C5 C7 -82.3(4) . . . . ?
C1 N1 C5 C6 -76.9(4) . . . . ?
C2 N1 C5 C6 150.3(3) . . . . ?
N1 C5 C6 C8 -58.6(5) . . . . ?
C7 C5 C6 C8 172.7(4) . . . . ?
N1 C5 C7 C9 155.7(3) . . . . ?
C6 C5 C7 C9 -78.3(5) . . . . ?
C14 C13 C12 C11 -0.2(10) . . . . ?
C15 C10 C11 C12 -2.2(8) . . . . ?
P1 C10 C11 C12 178.9(4) . . . . ?
C13 C12 C11 C10 2.4(10) . . . . ?

_refine_diff_density_max         0.612
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.061

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

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1560855'
_audit_update_record             
;
2017-07-07 deposited with the CCDC.
2017-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'[(dicopper,diiodo(K2-P,P))(1,8-di(iso-pentyl)-3,6,10,13-tetraphenyl-1,8-diaza-3,6,10,13-tetraphosphacyclotetradecane)]'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H58 Cu2 I2 N2 P4'
_chemical_formula_weight         1095.66

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'
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/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                   12.678(2)
_cell_length_b                   10.8332(17)
_cell_length_c                   17.285(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.697(2)
_cell_angle_gamma                90
_cell_volume                     2332.6(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9965
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      28.51
_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_F_000             1096
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    2.402
_shelx_estimated_absorpt_T_min   0.392
_shelx_estimated_absorpt_T_max   0.686
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.387
_exptl_absorpt_correction_T_max  0.658
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33928
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.635
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5623
_reflns_number_gt                4812
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0394P)²+0.9528P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5623
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0257
_refine_ls_wR_factor_ref         0.0770
_refine_ls_wR_factor_gt          0.0666
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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 0.25943(2) 0.22243(2) 0.61369(2) 0.05701(7) Uani 1 1 d . . . . .
Cu1 Cu 0.15758(2) 0.41646(2) 0.60813(2) 0.03740(8) Uani 1 1 d . . . . .
P2 P 0.00731(4) 0.45246(5) 0.65933(3) 0.03524(12) Uani 1 1 d . . . . .
P1 P 0.17748(4) 0.61989(5) 0.58804(3) 0.03438(12) Uani 1 1 d . . . . .
C3 C 0.07299(19) 0.6910(2) 0.63597(13) 0.0411(5) Uani 1 1 d . . . . .
H3A H 0.1021 0.7038 0.6914 0.049 Uiso 1 1 calc R U . . .
H3B H 0.0539 0.7712 0.6124 0.049 Uiso 1 1 calc R U . . .
C4 C -0.02829(18) 0.6113(2) 0.62808(14) 0.0416(5) Uani 1 1 d . . . . .
H4A H -0.0656 0.6115 0.5738 0.050 Uiso 1 1 calc R U . . .
H4B H -0.0761 0.6456 0.6603 0.050 Uiso 1 1 calc R U . . .
C16 C 0.04759(18) 0.4630(2) 0.76584(12) 0.0386(4) Uani 1 1 d . . . . .
C21 C 0.1404(2) 0.4023(2) 0.80191(14) 0.0480(5) Uani 1 1 d . . . . .
H21 H 0.1812 0.3587 0.7716 0.058 Uiso 1 1 calc R U . . .
C17 C -0.0122(2) 0.5282(2) 0.81193(14) 0.0477(5) Uani 1 1 d . . . . .
H17 H -0.0747 0.5687 0.7884 0.057 Uiso 1 1 calc R U . . .
C19 C 0.1128(3) 0.4717(3) 0.92763(15) 0.0603(7) Uani 1 1 d . . . . .
H19 H 0.1347 0.4745 0.9820 0.072 Uiso 1 1 calc R U . . .
C18 C 0.0208(3) 0.5330(3) 0.89268(15) 0.0564(7) Uani 1 1 d . . . . .
H18 H -0.0188 0.5773 0.9234 0.068 Uiso 1 1 calc R U . . .
C20 C 0.1721(2) 0.4068(3) 0.88289(15) 0.0586(7) Uani 1 1 d . . . . .
H20 H 0.2339 0.3657 0.9070 0.070 Uiso 1 1 calc R U . . .
N1 N 0.18700(14) 0.61701(18) 0.42899(10) 0.0375(4) Uani 1 1 d . . . . .
C10 C 0.29727(19) 0.7030(2) 0.63429(13) 0.0397(5) Uani 1 1 d . . . . .
C5 C 0.30213(19) 0.6487(3) 0.43218(15) 0.0487(6) Uani 1 1 d . . . . .
H5 H 0.3354 0.6533 0.4880 0.058 Uiso 1 1 calc R U . . .
C12 C 0.4778(2) 0.6962(3) 0.70798(19) 0.0682(8) Uani 1 1 d . . . . .
H12 H 0.5367 0.6508 0.7328 0.082 Uiso 1 1 calc R U . . .
C15 C 0.3037(2) 0.8306(3) 0.63523(17) 0.0580(7) Uani 1 1 d . . . . .
H15 H 0.2450 0.8772 0.6114 0.070 Uiso 1 1 calc R U . . .
C14 C 0.3968(3) 0.8895(3) 0.6713(2) 0.0734(9) Uani 1 1 d . . . . .
H14 H 0.4008 0.9752 0.6707 0.088 Uiso 1 1 calc R U . . .
C13 C 0.4829(3) 0.8219(3) 0.7078(2) 0.0717(9) Uani 1 1 d . . . . .
H13 H 0.5450 0.8618 0.7325 0.086 Uiso 1 1 calc R U . . .
C11 C 0.3856(2) 0.6357(3) 0.67153(15) 0.0525(6) Uani 1 1 d . . . . .
H11 H 0.3829 0.5499 0.6720 0.063 Uiso 1 1 calc R U . . .
C6 C 0.3184(3) 0.7753(3) 0.3961(2) 0.0695(9) Uani 1 1 d . . . . .
H6A H 0.3106 0.7665 0.3395 0.083 Uiso 1 1 calc R U . . .
H6B H 0.2629 0.8311 0.4065 0.083 Uiso 1 1 calc R U . . .
C7 C 0.3597(2) 0.5462(3) 0.39626(18) 0.0628(8) Uani 1 1 d . . . . .
H7A H 0.3275 0.5380 0.3410 0.075 Uiso 1 1 calc R U . . .
H7B H 0.4341 0.5697 0.3992 0.075 Uiso 1 1 calc R U . . .
C8 C 0.4281(3) 0.8320(5) 0.4285(3) 0.1113(16) Uani 1 1 d . . . . .
H8A H 0.4362 0.8418 0.4845 0.167 Uiso 1 1 calc R U . . .
H8B H 0.4335 0.9111 0.4045 0.167 Uiso 1 1 calc R U . . .
H8C H 0.4836 0.7786 0.4168 0.167 Uiso 1 1 calc R U . . .
C2 C 0.13924(17) 0.6828(2) 0.48754(12) 0.0372(4) Uani 1 1 d . . . . .
H2A H 0.0617 0.6798 0.4721 0.045 Uiso 1 1 calc R U . . .
H2B H 0.1608 0.7688 0.4880 0.045 Uiso 1 1 calc R U . . .
C9 C 0.3558(3) 0.4223(4) 0.4360(3) 0.0931(12) Uani 1 1 d . . . . .
H9A H 0.3764 0.4321 0.4919 0.140 Uiso 1 1 calc R U . . .
H9B H 0.4044 0.3663 0.4175 0.140 Uiso 1 1 calc R U . . .
H9C H 0.2842 0.3898 0.4237 0.140 Uiso 1 1 calc R U . . .
C1 C 0.12336(18) 0.6272(2) 0.35017(12) 0.0405(5) Uani 1 1 d . . . . .
H1A H 0.1633 0.5921 0.3127 0.049 Uiso 1 1 calc R U . . .
H1B H 0.1110 0.7138 0.3372 0.049 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 Cu1 2.4594(4) . ?
Cu1 P1 2.2524(7) . ?
Cu1 P2 2.2782(7) . ?
P2 C16 1.820(2) . ?
P2 C4 1.835(2) . ?
P2 C1 1.848(2) 3_566 ?
P1 C10 1.818(2) . ?
P1 C2 1.845(2) . ?
P1 C3 1.855(2) . ?
C3 C4 1.532(3) . ?
C16 C21 1.391(3) . ?
C16 C17 1.391(3) . ?
C21 C20 1.384(3) . ?
C17 C18 1.382(4) . ?
C19 C20 1.368(4) . ?
C19 C18 1.380(4) . ?
N1 C1 1.453(3) . ?
N1 C2 1.458(3) . ?
N1 C5 1.490(3) . ?
C10 C15 1.386(3) . ?
C10 C11 1.390(3) . ?
C5 C7 1.523(4) . ?
C5 C6 1.537(4) . ?
C12 C13 1.363(5) . ?
C12 C11 1.386(4) . ?
C15 C14 1.384(4) . ?
C14 C13 1.367(5) . ?
C6 C8 1.528(5) . ?
C7 C9 1.513(5) . ?
C1 P2 1.848(2) 3_566 ?

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
P1 Cu1 P2 91.03(2) . . ?
P1 Cu1 I1 140.28(2) . . ?
P2 Cu1 I1 127.010(19) . . ?
C16 P2 C4 104.25(11) . . ?
C16 P2 C1 101.40(10) . 3_566 ?
C4 P2 C1 104.15(11) . 3_566 ?
C16 P2 Cu1 107.80(8) . . ?
C4 P2 Cu1 102.94(7) . . ?
C1 P2 Cu1 133.32(8) 3_566 . ?
C10 P1 C2 106.44(10) . . ?
C10 P1 C3 101.85(11) . . ?
C2 P1 C3 100.50(10) . . ?
C10 P1 Cu1 121.66(8) . . ?
C2 P1 Cu1 119.30(8) . . ?
C3 P1 Cu1 103.18(8) . . ?
C4 C3 P1 112.46(15) . . ?
C3 C4 P2 110.25(15) . . ?
C21 C16 C17 119.3(2) . . ?
C21 C16 P2 118.61(18) . . ?
C17 C16 P2 122.07(19) . . ?
C20 C21 C16 120.0(3) . . ?
C18 C17 C16 120.1(3) . . ?
C20 C19 C18 120.5(2) . . ?
C19 C18 C17 119.9(3) . . ?
C19 C20 C21 120.2(3) . . ?
C1 N1 C2 112.56(17) . . ?
C1 N1 C5 112.75(17) . . ?
C2 N1 C5 113.07(18) . . ?
C15 C10 C11 118.5(2) . . ?
C15 C10 P1 122.83(18) . . ?
C11 C10 P1 118.65(19) . . ?
N1 C5 C7 110.9(2) . . ?
N1 C5 C6 113.3(2) . . ?
C7 C5 C6 112.0(2) . . ?
C13 C12 C11 120.5(3) . . ?
C14 C15 C10 120.6(3) . . ?
C13 C14 C15 120.1(3) . . ?
C12 C13 C14 120.2(3) . . ?
C12 C11 C10 120.1(3) . . ?
C8 C6 C5 113.1(3) . . ?
C9 C7 C5 113.8(2) . . ?
N1 C2 P1 113.72(15) . . ?
N1 C1 P2 112.35(15) . 3_566 ?

_refine_diff_density_max         0.810
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.081

