# 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_13S021
_database_code_depnum_ccdc_archive 'CCDC 1430441'
_audit_update_record             
;
2015-10-09 deposited with the CCDC.
2016-03-17 downloaded from the CCDC.
;
_audit_creation_date             2015-10-06
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_formula_moiety         'C38 H36 Cu2 P2'
_chemical_formula_sum            'C38 H36 Cu2 P2'
_chemical_formula_weight         681.75
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cu 0.34125 1.28947 13.33800 7.16760 5.61580 1.67350 3.58280 0.24700 11.39660
64.81260 1.19099998474
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
P 0.10434 0.09671 6.43450 4.17910 1.78000 1.49080 1.90670 27.15700 0.52600
68.16450 1.11489999294
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   10.0317(3)
_cell_length_b                   12.1017(4)
_cell_length_c                   13.3609(4)
_cell_angle_alpha                97.647(1)
_cell_angle_beta                 94.311(1)
_cell_angle_gamma                95.342(1)
_cell_volume                     1594.30(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9907
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.458
_exptl_absorpt_coefficient_mu    1.460
_exptl_absorpt_correction_T_max  0.9329
_exptl_absorpt_correction_T_min  0.7380
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0341 before and 0.0308 after correction.
The Ratio of minimum to maximum transmission is 0.7911.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.4200
_exptl_crystal_density_meas      .
_exptl_crystal_description       prism
_exptl_crystal_F_000             705.9452
_exptl_crystal_preparation       'cut from larger prism'
_exptl_crystal_size_max          0.595
_exptl_crystal_size_mid          0.283
_exptl_crystal_size_min          0.164
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24518
_diffrn_reflns_theta_full        25.9975
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.54
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9998
_diffrn_measured_fraction_theta_max 0.9998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                5660
_reflns_number_total             6267
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.4719
_refine_diff_density_min         -0.5334
_refine_diff_density_rms         0.1047
_refine_ls_d_res_high            0.8107
_refine_ls_d_res_low             13.1898
_refine_ls_goodness_of_fit_ref   1.0486
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    64
_refine_ls_number_parameters     391
_refine_ls_number_reflns         6267
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0247
_refine_ls_restrained_S_all      1.0484
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0626P)²+0.7017P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0916
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C2-H2c \\sim C2-H2b \\sim C2-H2a
 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C11(H11), C4(H4), C30(H30), C32(H32), C35(H35), C36(H36), C37(H37),
 C10(H10), C17(H17), C22(H22), C24(H24), C12(H12), C5(H5), C13(H13), C25(H25),
 C19(H19), C29(H29), C23(H23), C20(H20), C7(H7), C26(H26), C28(H28), C31(H31),
 C34(H34), C18(H18), C38(H38), C8(H8), C14(H14), C6(H6)
3.b Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c)
;
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_refinement_flags_posn
Cu1 Cu 0.28238(2) 0.169984(19) 0.686292(17) 0.01146(8) Uani 1.000000 .
Cu2 Cu 0.52057(2) 0.21365(2) 0.731711(19) 0.01830(9) Uani 1.000000 .
P2 P 0.20321(5) 0.30736(4) 0.60669(4) 0.01027(11) Uani 1.000000 .
P1 P 0.17441(5) 0.09625(4) 0.80830(4) 0.01136(12) Uani 1.000000 .
C16 C -0.0265(2) -0.08605(17) 0.80838(15) 0.0162(4) Uani 1.000000 .
H16 H 0.0352(2) -0.11564(17) 0.85256(15) 0.0195(5) Uiso 1.000000 R
C11 C 0.2373(3) 0.35851(19) 1.03890(17) 0.0267(5) Uani 1.000000 .
H11 H 0.3128(3) 0.39658(19) 1.08087(17) 0.0321(6) Uiso 1.000000 R
C4 C 0.3656(2) -0.05181(17) 0.83869(16) 0.0166(4) Uani 1.000000 .
H4 H 0.3872(2) -0.04289(17) 0.77201(16) 0.0199(5) Uiso 1.000000 R
C30 C 0.4231(2) 0.41163(18) 0.33629(16) 0.0197(4) Uani 1.000000 .
H30 H 0.4699(2) 0.43457(18) 0.28211(16) 0.0237(5) Uiso 1.000000 R
C32 C 0.2167(2) 0.38546(16) 0.41592(15) 0.0141(4) Uani 1.000000 .
H32 H 0.1227(2) 0.39059(16) 0.41562(15) 0.0169(5) Uiso 1.000000 R
C35 C 0.2646(2) 0.5551(2) 0.85038(17) 0.0246(5) Uani 1.000000 .
H35 H 0.3034(2) 0.5627(2) 0.91835(17) 0.0296(6) Uiso 1.000000 R
C36 C 0.2099(2) 0.64454(18) 0.81416(17) 0.0228(5) Uani 1.000000 .
H36 H 0.2092(2) 0.71305(18) 0.85795(17) 0.0274(6) Uiso 1.000000 R
C21 C 0.02716(19) 0.27291(16) 0.55836(14) 0.0120(4) Uani 1.000000 .
C37 C 0.1562(2) 0.63460(18) 0.71410(17) 0.0208(4) Uani 1.000000 .
H37 H 0.1197(2) 0.69654(18) 0.68954(17) 0.0250(5) Uiso 1.000000 R
C10 C 0.2538(2) 0.26740(18) 0.96704(16) 0.0207(5) Uani 1.000000 .
H10 H 0.3409(2) 0.24427(18) 0.95956(16) 0.0248(5) Uiso 1.000000 R
C33 C 0.20707(19) 0.44247(16) 0.68629(15) 0.0123(4) Uani 1.000000 .
C27 C 0.28479(19) 0.34469(16) 0.49593(14) 0.0123(4) Uani 1.000000 .
C17 C -0.1531(2) -0.14395(17) 0.77868(16) 0.0193(4) Uani 1.000000 .
H17 H -0.1769(2) -0.21307(17) 0.80247(16) 0.0232(5) Uiso 1.000000 R
C22 C -0.0779(2) 0.32322(17) 0.60298(16) 0.0158(4) Uani 1.000000 .
H22 H -0.0587(2) 0.38398(17) 0.65652(16) 0.0190(5) Uiso 1.000000 R
C3 C 0.26599(19) 0.00605(16) 0.88183(15) 0.0134(4) Uani 1.000000 .
C15 C 0.00985(19) 0.01544(16) 0.77333(14) 0.0134(4) Uani 1.000000 .
C24 C -0.2399(2) 0.19548(18) 0.49125(16) 0.0194(4) Uani 1.000000 .
H24 H -0.3307(2) 0.16959(18) 0.46806(16) 0.0233(5) Uiso 1.000000 R
C12 C 0.1113(3) 0.39347(19) 1.04913(17) 0.0293(5) Uani 1.000000 .
H12 H 0.1001(3) 0.45574(19) 1.09797(17) 0.0351(7) Uiso 1.000000 R
C5 C 0.4340(2) -0.12299(18) 0.89322(18) 0.0215(5) Uani 1.000000 .
H5 H 0.5018(2) -0.16267(18) 0.86346(18) 0.0258(5) Uiso 1.000000 R
C13 C 0.0017(3) 0.3379(2) 0.98834(19) 0.0289(5) Uani 1.000000 .
H13 H -0.0848(3) 0.3623(2) 0.99545(19) 0.0346(6) Uiso 1.000000 R
C25 C -0.1364(2) 0.14441(18) 0.44733(16) 0.0199(4) Uani 1.000000 .
H25 H -0.1563(2) 0.08316(18) 0.39432(16) 0.0238(5) Uiso 1.000000 R
C19 C -0.2090(2) -0.00163(19) 0.67865(16) 0.0198(4) Uani 1.000000 .
H19 H -0.2714(2) 0.02750(19) 0.63461(16) 0.0237(5) Uiso 1.000000 R
C29 C 0.4915(2) 0.37100(19) 0.41543(17) 0.0210(5) Uani 1.000000 .
H29 H 0.5854(2) 0.36589(19) 0.41537(17) 0.0252(5) Uiso 1.000000 R
C23 C -0.2109(2) 0.28441(18) 0.56905(17) 0.0185(4) Uani 1.000000 .
H23 H -0.2820(2) 0.31904(18) 0.59937(17) 0.0222(5) Uiso 1.000000 R
C20 C -0.0820(2) 0.05602(18) 0.70699(16) 0.0172(4) Uani 1.000000 .
H20 H -0.0577(2) 0.12365(18) 0.68089(16) 0.0206(5) Uiso 1.000000 R
C7 C 0.3035(2) -0.07866(18) 1.03407(16) 0.0210(5) Uani 1.000000 .
H7 H 0.2821(2) -0.08806(18) 1.10069(16) 0.0252(5) Uiso 1.000000 R
C26 C -0.0038(2) 0.18256(18) 0.48062(15) 0.0173(4) Uani 1.000000 .
H26 H 0.0667(2) 0.14700(18) 0.45034(15) 0.0207(5) Uiso 1.000000 R
C1 C 0.6163(3) 0.3331(2) 0.82743(19) 0.0298(5) Uani 1.000000 .
H1a H 0.6430(16) 0.3966(6) 0.7922(3) 0.0447(8) Uiso 1.000000 GR
H1b H 0.5579(6) 0.3569(10) 0.8801(8) 0.0447(8) Uiso 1.000000 GR
H1c H 0.6966(10) 0.3065(5) 0.8587(10) 0.0447(8) Uiso 1.000000 GR
C28 C 0.4228(2) 0.33768(17) 0.49500(16) 0.0168(4) Uani 1.000000 .
H28 H 0.4702(2) 0.30997(17) 0.54904(16) 0.0201(5) Uiso 1.000000 R
C31 C 0.2856(2) 0.41863(17) 0.33661(15) 0.0178(4) Uani 1.000000 .
H31 H 0.2385(2) 0.44621(17) 0.28237(15) 0.0214(5) Uiso 1.000000 R
C9 C 0.1433(2) 0.20985(16) 0.90595(15) 0.0150(4) Uani 1.000000 .
C34 C 0.2625(2) 0.45366(18) 0.78650(16) 0.0187(4) Uani 1.000000 .
H34 H 0.2990(2) 0.39190(18) 0.81143(16) 0.0225(5) Uiso 1.000000 R
C18 C -0.2442(2) -0.10163(18) 0.71493(16) 0.0201(4) Uani 1.000000 .
H18 H -0.3308(2) -0.14091(18) 0.69597(16) 0.0241(5) Uiso 1.000000 R
C38 C 0.1557(2) 0.53469(17) 0.65005(16) 0.0165(4) Uani 1.000000 .
H38 H 0.1204(2) 0.52872(17) 0.58132(16) 0.0198(5) Uiso 1.000000 R
C8 C 0.2352(2) -0.00791(17) 0.98028(15) 0.0177(4) Uani 1.000000 .
H8 H 0.1673(2) 0.03137(17) 1.01026(15) 0.0213(5) Uiso 1.000000 R
C14 C 0.0169(2) 0.24619(19) 0.91655(18) 0.0223(5) Uani 1.000000 .
H14 H -0.0591(2) 0.20854(19) 0.87488(18) 0.0268(6) Uiso 1.000000 R
C6 C 0.4034(2) -0.13598(18) 0.99045(17) 0.0224(5) Uani 1.000000 .
H6 H 0.4507(2) -0.18412(18) 1.02752(17) 0.0268(6) Uiso 1.000000 R
C2 C 0.4433(2) 0.09033(18) 0.62184(17) 0.0203(4) Uani 1.000000 D
H2a H 0.357(2) 0.060(2) 0.5838(19) 0.027(7) Uiso 1.000000 D
H2b H 0.492(3) 0.113(2) 0.5668(17) 0.030(7) Uiso 1.000000 D
H2c H 0.483(3) 0.026(2) 0.646(2) 0.040(8) Uiso 1.000000 D


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 Cu2 2.4121(3) . y
Cu1 P2 2.2617(5) . y
Cu1 P1 2.2582(5) . y
Cu1 C2 2.134(2) . y
Cu2 C1 1.926(2) . y
Cu2 C2 2.003(2) . y
P2 C21 1.825(2) . ?
P2 C33 1.824(2) . ?
P2 C27 1.832(2) . ?
P1 C3 1.827(2) . ?
P1 C15 1.834(2) . ?
P1 C9 1.831(2) . ?
C16 C17 1.395(3) . ?
C16 C15 1.399(3) . ?
C11 C10 1.393(3) . ?
C11 C12 1.380(4) . ?
C4 C3 1.390(3) . ?
C4 C5 1.395(3) . ?
C30 C29 1.387(3) . ?
C30 C31 1.390(3) . ?
C32 C27 1.395(3) . ?
C32 C31 1.391(3) . ?
C35 C36 1.385(3) . ?
C35 C34 1.396(3) . ?
C36 C37 1.389(3) . ?
C21 C22 1.398(3) . ?
C21 C26 1.399(3) . ?
C37 C38 1.385(3) . ?
C10 C9 1.396(3) . ?
C33 C34 1.395(3) . ?
C33 C38 1.400(3) . ?
C27 C28 1.396(3) . ?
C17 C18 1.382(3) . ?
C22 C23 1.393(3) . ?
C3 C8 1.401(3) . ?
C15 C20 1.398(3) . ?
C24 C25 1.385(3) . ?
C24 C23 1.386(3) . ?
C12 C13 1.380(4) . ?
C5 C6 1.383(3) . ?
C13 C14 1.394(3) . ?
C25 C26 1.386(3) . ?
C19 C20 1.395(3) . ?
C19 C18 1.388(3) . ?
C29 C28 1.393(3) . ?
C7 C8 1.385(3) . ?
C7 C6 1.391(3) . ?
C9 C14 1.392(3) . ?

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
P2 Cu1 Cu2 109.573(16) . . ?
P1 Cu1 Cu2 112.728(16) . . ?
P1 Cu1 P2 122.331(19) . . ?
C2 Cu1 Cu2 51.86(6) . . ?
C2 Cu1 P2 116.56(6) . . ?
C2 Cu1 P1 120.09(6) . . ?
C1 Cu2 Cu1 129.96(8) . . ?
C2 Cu2 Cu1 56.90(6) . . ?
C2 Cu2 C1 172.25(10) . . ?
C21 P2 Cu1 111.96(6) . . ?
C33 P2 Cu1 114.86(7) . . ?
C33 P2 C21 104.33(9) . . ?
C27 P2 Cu1 118.09(6) . . ?
C27 P2 C21 103.36(9) . . ?
C27 P2 C33 102.67(9) . . ?
C3 P1 Cu1 116.92(7) . . ?
C15 P1 Cu1 118.64(6) . . ?
C15 P1 C3 103.43(9) . . ?
C9 P1 Cu1 109.08(6) . . ?
C9 P1 C3 102.29(9) . . ?
C9 P1 C15 104.67(9) . . ?
C15 C16 C17 120.22(19) . . ?
C12 C11 C10 120.0(2) . . ?
C5 C4 C3 120.05(19) . . ?
C31 C30 C29 119.70(19) . . ?
C31 C32 C27 120.35(18) . . ?
C34 C35 C36 119.7(2) . . ?
C37 C36 C35 120.3(2) . . ?
C22 C21 P2 123.17(15) . . ?
C26 C21 P2 117.50(15) . . ?
C26 C21 C22 118.88(18) . . ?
C38 C37 C36 120.2(2) . . ?
C9 C10 C11 120.5(2) . . ?
C34 C33 P2 118.74(15) . . ?
C38 C33 P2 122.05(15) . . ?
C38 C33 C34 119.21(18) . . ?
C32 C27 P2 122.90(15) . . ?
C28 C27 P2 118.00(15) . . ?
C28 C27 C32 119.00(18) . . ?
C18 C17 C16 120.55(19) . . ?
C23 C22 C21 120.12(19) . . ?
C4 C3 P1 119.54(15) . . ?
C8 C3 P1 121.08(15) . . ?
C8 C3 C4 119.37(18) . . ?
C16 C15 P1 122.89(15) . . ?
C20 C15 P1 118.41(15) . . ?
C20 C15 C16 118.68(18) . . ?
C23 C24 C25 119.95(19) . . ?
C13 C12 C11 119.9(2) . . ?
C6 C5 C4 120.2(2) . . ?
C14 C13 C12 120.6(2) . . ?
C26 C25 C24 120.1(2) . . ?
C18 C19 C20 119.9(2) . . ?
C28 C29 C30 120.12(19) . . ?
C24 C23 C22 120.30(19) . . ?
C19 C20 C15 120.75(19) . . ?
C6 C7 C8 119.9(2) . . ?
C25 C26 C21 120.64(19) . . ?
C29 C28 C27 120.50(19) . . ?
C32 C31 C30 120.34(19) . . ?
C10 C9 P1 117.88(16) . . ?
C14 C9 P1 122.94(17) . . ?
C14 C9 C10 119.0(2) . . ?
C33 C34 C35 120.4(2) . . ?
C19 C18 C17 119.89(19) . . ?
C33 C38 C37 120.17(19) . . ?
C7 C8 C3 120.3(2) . . ?
C9 C14 C13 120.0(2) . . ?
C7 C6 C5 120.1(2) . . ?
Cu2 C2 Cu1 71.25(7) . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perflourotether oil'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_equal_distance_atom_site_label_1
_restr_equal_distance_atom_site_label_2
_restr_equal_distance_site_symmetry_2
_restr_equal_distance_class_id
C2 H2a 1 1
C2 H2b 1 1
C2 H2c 1 1

loop_
_restr_equal_distance_class_class_id
_restr_equal_distance_class_target_weight_param
_restr_equal_distance_class_average
_restr_equal_distance_class_esd
_restr_equal_distance_class_diff_max
1 0.0200 0.9805 0.0109 0.0140

_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Oxygen-sensitive'
