# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_xl
_database_code_depnum_ccdc_archive 'CCDC 1446745'
_audit_update_record             
;
2016-01-12 deposited with the CCDC.
2016-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H40 Cl4 Cu4 N2 P2'
_chemical_formula_sum            'C40 H40 Cl4 Cu4 N2 P2'
_chemical_formula_weight         1006.64

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'
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'

_symmetry_cell_setting           monoclinic

_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   11.1272(3)
_cell_length_b                   13.5250(4)
_cell_length_c                   13.4866(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.147(3)
_cell_angle_gamma                90.00
_cell_volume                     1968.11(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7896
_cell_measurement_theta_min      4.10
_cell_measurement_theta_max      74.74

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016
_exptl_absorpt_coefficient_mu    2.518
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7039
_exptl_absorpt_correction_T_max  0.7869
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  SuperNova
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7622
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         26.40
_reflns_number_total             3922
_reflns_number_gt                3366
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0862P)²+1.4333P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3922
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1369
_refine_ls_wR_factor_gt          0.1291
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.89178(5) 0.07677(4) 0.34365(4) 0.02791(17) Uani 1 1 d . . .
Cu2 Cu 0.88773(5) 0.00918(4) 0.54844(4) 0.02587(17) Uani 1 1 d . . .
Cl1 Cl 0.91794(7) -0.09186(6) 0.40309(6) 0.01420(19) Uani 1 1 d . . .
Cl2 Cl 0.76292(8) 0.12720(6) 0.43898(6) 0.01564(19) Uani 1 1 d . . .
P1 P 0.81806(8) -0.07546(6) 0.66163(6) 0.0112(2) Uani 1 1 d . . .
N1 N 1.0523(3) -0.1144(2) 0.7788(2) 0.0132(6) Uani 1 1 d . . .
C1 C 0.9316(3) -0.1077(3) 0.7806(3) 0.0138(7) Uani 1 1 d . . .
C2 C 1.1365(3) -0.1401(3) 0.8657(3) 0.0152(7) Uani 1 1 d . . .
C3 C 1.1018(3) -0.1566(3) 0.9560(3) 0.0195(7) Uani 1 1 d . . .
H3A H 1.1630 -0.1721 1.0165 0.023 Uiso 1 1 calc R . .
C4 C 0.9800(4) -0.1506(3) 0.9588(3) 0.0199(8) Uani 1 1 d . . .
H4A H 0.9556 -0.1631 1.0204 0.024 Uiso 1 1 calc R . .
C5 C 0.8926(3) -0.1261(3) 0.8696(3) 0.0177(7) Uani 1 1 d . . .
H5A H 0.8073 -0.1218 0.8693 0.021 Uiso 1 1 calc R . .
C6 C 1.2696(3) -0.1514(3) 0.8622(3) 0.0207(7) Uani 1 1 d . . .
H6A H 1.2780 -0.1369 0.7930 0.031 Uiso 1 1 calc R . .
H6B H 1.2969 -0.2193 0.8807 0.031 Uiso 1 1 calc R . .
H6C H 1.3209 -0.1053 0.9107 0.031 Uiso 1 1 calc R . .
C7 C 0.7022(3) -0.0129(3) 0.7153(3) 0.0147(7) Uani 1 1 d . . .
C8 C 0.7313(3) 0.0817(3) 0.7581(3) 0.0167(7) Uani 1 1 d . . .
C9 C 0.6436(3) 0.1289(3) 0.8008(3) 0.0193(7) Uani 1 1 d . . .
H9A H 0.6615 0.1926 0.8303 0.023 Uiso 1 1 calc R . .
C10 C 0.5319(4) 0.0849(3) 0.8012(3) 0.0241(8) Uani 1 1 d . . .
H10A H 0.4741 0.1183 0.8308 0.029 Uiso 1 1 calc R . .
C11 C 0.5039(4) -0.0076(3) 0.7585(3) 0.0235(8) Uani 1 1 d . . .
H11A H 0.4267 -0.0376 0.7584 0.028 Uiso 1 1 calc R . .
C12 C 0.5886(3) -0.0569(3) 0.7157(3) 0.0190(7) Uani 1 1 d . . .
H12A H 0.5692 -0.1206 0.6866 0.023 Uiso 1 1 calc R . .
C13 C 0.8529(3) 0.1318(3) 0.7618(3) 0.0210(8) Uani 1 1 d . . .
H13A H 0.8542 0.1967 0.7945 0.031 Uiso 1 1 calc R . .
H13B H 0.8629 0.1403 0.6921 0.031 Uiso 1 1 calc R . .
H13C H 0.9208 0.0912 0.8013 0.031 Uiso 1 1 calc R . .
C14 C 0.7541(3) -0.1964(3) 0.6155(3) 0.0152(7) Uani 1 1 d . . .
C15 C 0.6614(3) -0.2032(3) 0.5226(3) 0.0177(7) Uani 1 1 d . . .
C16 C 0.6262(3) -0.2974(3) 0.4832(3) 0.0197(7) Uani 1 1 d . . .
H16A H 0.5636 -0.3030 0.4213 0.024 Uiso 1 1 calc R . .
C17 C 0.6794(4) -0.3827(3) 0.5314(3) 0.0210(8) Uani 1 1 d . . .
H17A H 0.6553 -0.4455 0.5017 0.025 Uiso 1 1 calc R . .
C18 C 0.7681(4) -0.3757(3) 0.6232(3) 0.0197(7) Uani 1 1 d . . .
H18A H 0.8038 -0.4339 0.6575 0.024 Uiso 1 1 calc R . .
C19 C 0.8047(3) -0.2836(3) 0.6651(3) 0.0167(7) Uani 1 1 d . . .
H19A H 0.8651 -0.2795 0.7284 0.020 Uiso 1 1 calc R . .
C20 C 0.6009(4) -0.1136(3) 0.4657(3) 0.0262(9) Uani 1 1 d . . .
H20A H 0.5395 -0.1345 0.4041 0.039 Uiso 1 1 calc R . .
H20B H 0.6640 -0.0725 0.4463 0.039 Uiso 1 1 calc R . .
H20C H 0.5599 -0.0754 0.5097 0.039 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 1.968(3) 3_756 ?
Cu1 Cl2 2.2528(10) . ?
Cu1 Cl1 2.4115(10) . ?
Cu1 Cu2 2.7827(7) 3_756 ?
Cu1 Cu2 2.9202(7) . ?
Cu2 P1 2.1955(10) . ?
Cu2 Cl2 2.3778(9) . ?
Cu2 Cl1 2.3796(9) 3_756 ?
Cu2 Cl1 2.4791(9) . ?
Cu2 Cu1 2.7827(8) 3_756 ?
Cl1 Cu2 2.3796(9) 3_756 ?
P1 C14 1.831(4) . ?
P1 C7 1.832(4) . ?
P1 C1 1.836(3) . ?
N1 C1 1.352(5) . ?
N1 C2 1.354(4) . ?
N1 Cu1 1.968(3) 3_756 ?
C1 C5 1.395(5) . ?
C2 C3 1.383(5) . ?
C2 C6 1.501(5) . ?
C3 C4 1.368(5) . ?
C4 C5 1.390(5) . ?
C7 C12 1.398(5) . ?
C7 C8 1.409(5) . ?
C8 C9 1.403(5) . ?
C8 C13 1.502(5) . ?
C9 C10 1.379(6) . ?
C10 C11 1.380(6) . ?
C11 C12 1.390(6) . ?
C14 C19 1.404(5) . ?
C14 C15 1.418(5) . ?
C15 C16 1.399(5) . ?
C15 C20 1.502(5) . ?
C16 C17 1.384(6) . ?
C17 C18 1.386(5) . ?
C18 C19 1.387(5) . ?

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 Cu1 Cl2 140.93(9) 3_756 . ?
N1 Cu1 Cl1 119.07(9) 3_756 . ?
Cl2 Cu1 Cl1 97.96(3) . . ?
N1 Cu1 Cu2 97.33(9) 3_756 3_756 ?
Cl2 Cu1 Cu2 115.52(3) . 3_756 ?
Cl1 Cu1 Cu2 53.96(2) . 3_756 ?
N1 Cu1 Cu2 162.84(9) 3_756 . ?
Cl2 Cu1 Cu2 52.83(2) . . ?
Cl1 Cu1 Cu2 54.41(2) . . ?
Cu2 Cu1 Cu2 65.79(2) 3_756 . ?
P1 Cu2 Cl2 121.99(4) . . ?
P1 Cu2 Cl1 120.37(4) . 3_756 ?
Cl2 Cu2 Cl1 102.05(3) . 3_756 ?
P1 Cu2 Cl1 113.67(4) . . ?
Cl2 Cu2 Cl1 92.90(3) . . ?
Cl1 Cu2 Cl1 100.75(3) 3_756 . ?
P1 Cu2 Cu1 80.48(3) . 3_756 ?
Cl2 Cu2 Cu1 155.74(3) . 3_756 ?
Cl1 Cu2 Cu1 55.03(3) 3_756 3_756 ?
Cl1 Cu2 Cu1 84.87(3) . 3_756 ?
P1 Cu2 Cu1 155.58(3) . . ?
Cl2 Cu2 Cu1 49.03(2) . . ?
Cl1 Cu2 Cu1 83.67(3) 3_756 . ?
Cl1 Cu2 Cu1 52.28(2) . . ?
Cu1 Cu2 Cu1 114.21(2) 3_756 . ?
Cu2 Cl1 Cu1 71.01(3) 3_756 . ?
Cu2 Cl1 Cu2 79.25(3) 3_756 . ?
Cu1 Cl1 Cu2 73.31(3) . . ?
Cu1 Cl2 Cu2 78.14(3) . . ?
C14 P1 C7 107.10(16) . . ?
C14 P1 C1 102.24(16) . . ?
C7 P1 C1 99.49(16) . . ?
C14 P1 Cu2 113.80(12) . . ?
C7 P1 Cu2 115.83(12) . . ?
C1 P1 Cu2 116.56(12) . . ?
C1 N1 C2 118.8(3) . . ?
C1 N1 Cu1 121.1(2) . 3_756 ?
C2 N1 Cu1 119.9(2) . 3_756 ?
N1 C1 C5 121.6(3) . . ?
N1 C1 P1 118.3(3) . . ?
C5 C1 P1 120.1(3) . . ?
N1 C2 C3 121.4(3) . . ?
N1 C2 C6 118.6(3) . . ?
C3 C2 C6 120.1(3) . . ?
C4 C3 C2 120.4(3) . . ?
C3 C4 C5 118.6(3) . . ?
C4 C5 C1 119.2(3) . . ?
C12 C7 C8 120.1(3) . . ?
C12 C7 P1 122.0(3) . . ?
C8 C7 P1 117.9(3) . . ?
C9 C8 C7 117.9(3) . . ?
C9 C8 C13 119.5(3) . . ?
C7 C8 C13 122.6(3) . . ?
C10 C9 C8 121.6(4) . . ?
C9 C10 C11 120.0(4) . . ?
C10 C11 C12 120.1(4) . . ?
C11 C12 C7 120.2(4) . . ?
C19 C14 C15 119.2(3) . . ?
C19 C14 P1 120.7(3) . . ?
C15 C14 P1 119.7(3) . . ?
C16 C15 C14 118.0(3) . . ?
C16 C15 C20 119.5(3) . . ?
C14 C15 C20 122.5(3) . . ?
C17 C16 C15 122.2(3) . . ?
C16 C17 C18 119.5(4) . . ?
C17 C18 C19 120.0(4) . . ?
C18 C19 C14 121.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        26.40
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         1.266
_refine_diff_density_min         -1.030
_refine_diff_density_rms         0.131
