# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_1dash
_database_code_depnum_ccdc_archive 'CCDC 1433403'
_audit_update_record             
;
2015-11-06 deposited with the CCDC.
2015-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C54 H52 Cu2 N4 O8 P2, 2(N O3), 4(C H4 O)'
_chemical_formula_sum            'C58 H68 Cu2 N6 O18 P2'
_chemical_formula_weight         1324.3

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'


_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.3974(12)
_cell_length_b                   11.5337(12)
_cell_length_c                   12.5848(13)
_cell_angle_alpha                117.067(4)
_cell_angle_beta                 101.070(4)
_cell_angle_gamma                101.147(4)
_cell_volume                     1369.1(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    103
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      26.00

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.61
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             614
_exptl_absorpt_coefficient_mu    0.920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.878
_exptl_absorpt_correction_T_max  0.913
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16802
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5127
_reflns_number_gt                4340
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker kappa Apex'
_computing_cell_refinement       'Bruker kappa Apex'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker XSHELL'
_computing_publication_material  'Bruker XSHELL'

_refine_special_details          
;

Nitrate molecule was heavily disordered hence, in order to model the electron 
density, the applied constraints are listed herein.

DFIX 1.25 0.01 N3 O5 N3 O6 N3 O7 N3A O5A N3A O6A N3A O7A
DFIX 2.16 0.01 O5 O6 O6 O7 O7 O5
DFIX 2.16 0.01 O5A O6A O6A O7A O7A O5A
FLAT N3 O5 O6 O7
FLAT N3A O5A O6A O7A
SIMU 0.01 0.02 2.90 N3 O5 O6 O7 N3A O5A O6A O7A

 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.

_platon_squeeze_details
loop_
  _platon_squeeze_void_nr
  _platon_squeeze_void_average_x
  _platon_squeeze_void_average_y
  _platon_squeeze_void_average_z
  _platon_squeeze_void_volume
  _platon_squeeze_void_count_electrons
  _platon_squeeze_void_content
   1  0.000  0.500  0.500       114        36 ' '
   2  0.500  0.500  1.000        57        34 ' '

_platon_squeeze_details 
loop_                          
The squeeze software (Platon) cannot calculate the absolute value of electrons
that are removed and however 70 elcetrons is very close to four molecules of 
methanol per unit cell (i.e. 72 electrons).Hence, it has been assumed that there
are two molecules of metahnol in an asymmetric unit. Notably, the SQUEEZE treated
structure is very stable with minimal IUCr checkcif problems, improved R factor 
and goodness of fit. 
 
;

_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)+(0.0516P)²+6.7610P] 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         5127
_refine_ls_number_parameters     348
_refine_ls_number_restraints     41
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1610
_refine_ls_wR_factor_gt          0.1566
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_restrained_S_all      1.212
_refine_ls_shift/su_max          0.003
_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 0.48170(5) 0.99088(6) 0.19451(5) 0.01178(18) Uani 1 1 d . . 4
P1 P 0.33466(11) 0.85125(12) -0.10875(11) 0.0119(3) Uani 1 1 d . A 4
O1 O 0.4259(3) 0.8826(3) 0.0114(3) 0.0151(7) Uani 1 1 d . A 4
O2 O 0.2430(3) 0.6968(3) -0.1768(3) 0.0154(7) Uani 1 1 d . A 4
O3 O 0.3917(3) 0.8627(3) -0.2034(3) 0.0142(7) Uani 1 1 d . . 4
O4 O 0.6175(3) 0.8782(4) 0.2093(4) 0.0293(9) Uani 1 1 d . B 4
O5 O 0.8514(7) 1.0153(8) 0.3880(7) 0.0317(18) Uiso 0.50 1 d PDU C -1
O5A O 0.851(2) 0.9214(16) 0.420(2) 0.173(7) Uiso 0.50 1 d PDU D -2
O6 O 1.0368(8) 1.0787(9) 0.5265(9) 0.047(2) Uiso 0.50 1 d PDU C -1
O6A O 0.8492(8) 1.0880(9) 0.3848(8) 0.040(2) Uiso 0.50 1 d PDU D -2
O7 O 0.9099(10) 0.8716(9) 0.4369(11) 0.065(3) Uiso 0.50 1 d PDU C -1
O7A O 0.9925(18) 1.121(2) 0.5475(17) 0.156(6) Uiso 0.50 1 d PDU D -2
N1 N 0.3422(4) 0.8690(4) 0.2098(4) 0.0160(8) Uani 1 1 d . E 4
N2 N 0.4984(4) 1.1115(4) 0.3765(4) 0.0140(8) Uani 1 1 d . E 4
N3 N 0.9341(7) 0.9901(8) 0.4534(8) 0.028(2) Uiso 0.50 1 d PDU C -1
N3A N 0.8931(16) 1.0464(16) 0.4540(15) 0.131(6) Uiso 0.50 1 d PDU D -2
C1 C 0.2262(4) 0.9486(5) -0.0834(4) 0.0143(9) Uani 1 1 d . A 4
H1A H 0.2672 1.0366 -0.0733 0.017 Uiso 1 1 calc R A 4
H1B H 0.1538 0.9007 -0.1593 0.017 Uiso 1 1 calc R A 4
C2 C 0.1777(4) 0.9763(5) 0.0272(5) 0.0153(10) Uani 1 1 d . A 4
C3 C 0.0713(4) 0.8777(5) 0.0136(5) 0.0153(10) Uani 1 1 d . A 4
C4 C 0.0052(4) 0.7503(5) -0.1021(5) 0.0178(10) Uani 1 1 d . A 4
H4 H 0.0336 0.7290 -0.1711 0.021 Uiso 1 1 calc R A 4
C5 C -0.0987(5) 0.6600(5) -0.1118(5) 0.0222(11) Uani 1 1 d . A 4
H5 H -0.1396 0.5774 -0.1875 0.027 Uiso 1 1 calc R A 4
C6 C -0.1462(5) 0.6890(5) -0.0089(5) 0.0220(11) Uani 1 1 d . A 4
H6 H -0.2190 0.6271 -0.0187 0.026 Uiso 1 1 calc R A 4
C7 C -0.0856(5) 0.8064(5) 0.1027(5) 0.0226(11) Uani 1 1 d . A 4
H7 H -0.1153 0.8235 0.1705 0.027 Uiso 1 1 calc R A 4
C8 C 0.0244(4) 0.9051(5) 0.1180(5) 0.0164(10) Uani 1 1 d . A 4
C9 C 0.0851(5) 1.0279(5) 0.2332(5) 0.0179(10) Uani 1 1 d . A 4
H9 H 0.0553 1.0444 0.3008 0.021 Uiso 1 1 calc R A 4
C10 C 0.1895(5) 1.1257(5) 0.2478(5) 0.0158(10) Uani 1 1 d . A 4
C11 C 0.2495(5) 1.2510(5) 0.3655(5) 0.0192(10) Uani 1 1 d . A 4
H11 H 0.2210 1.2647 0.4335 0.023 Uiso 1 1 calc R A 4
C12 C 0.3475(5) 1.3505(5) 0.3797(5) 0.0214(11) Uani 1 1 d . A 4
H12 H 0.3848 1.4327 0.4564 0.026 Uiso 1 1 calc R A 4
C13 C 0.3930(5) 1.3287(5) 0.2775(5) 0.0207(11) Uani 1 1 d . A 4
H13 H 0.4597 1.3980 0.2881 0.025 Uiso 1 1 calc R A 4
C14 C 0.3418(4) 1.2090(5) 0.1638(5) 0.0167(10) Uani 1 1 d . A 4
H14 H 0.3750 1.1975 0.0990 0.020 Uiso 1 1 calc R A 4
C15 C 0.2375(4) 1.1010(5) 0.1434(5) 0.0147(10) Uani 1 1 d . A 4
C16 C 0.2988(5) 0.5871(5) -0.2156(5) 0.0238(11) Uani 1 1 d . A 4
H16A H 0.3759 0.6125 -0.1500 0.029 Uiso 1 1 calc R A 4
H16B H 0.3192 0.5703 -0.2916 0.029 Uiso 1 1 calc R A 4
C17 C 0.2040(6) 0.4592(5) -0.2397(6) 0.0328(14) Uani 1 1 d . A 4
H17A H 0.1890 0.4746 -0.1625 0.049 Uiso 1 1 calc R A 4
H17B H 0.2365 0.3836 -0.2710 0.049 Uiso 1 1 calc R A 4
H17C H 0.1263 0.4382 -0.3008 0.049 Uiso 1 1 calc R A 4
C18 C 0.2692(5) 0.7418(5) 0.1181(5) 0.0186(10) Uani 1 1 d . E 4
H18 H 0.2848 0.7031 0.0415 0.022 Uiso 1 1 calc R E 4
C19 C 0.1715(5) 0.6666(5) 0.1341(5) 0.0228(11) Uani 1 1 d . E 4
H19 H 0.1206 0.5795 0.0683 0.027 Uiso 1 1 calc R E 4
C20 C 0.1502(5) 0.7221(6) 0.2490(6) 0.0250(12) Uani 1 1 d . E 4
H20 H 0.0859 0.6720 0.2620 0.030 Uiso 1 1 calc R E 4
C21 C 0.2260(5) 0.8535(6) 0.3446(5) 0.0222(11) Uani 1 1 d . E 4
H21 H 0.2123 0.8935 0.4220 0.027 Uiso 1 1 calc R E 4
C22 C 0.3230(5) 0.9246(5) 0.3229(5) 0.0165(10) Uani 1 1 d . E 4
C23 C 0.4113(5) 1.0616(5) 0.4165(5) 0.0176(10) Uani 1 1 d . E 4
C24 C 0.4083(5) 1.1370(6) 0.5394(5) 0.0225(11) Uani 1 1 d . E 4
H24 H 0.3465 1.1019 0.5654 0.027 Uiso 1 1 calc R E 4
C25 C 0.4986(5) 1.2642(6) 0.6217(5) 0.0246(11) Uani 1 1 d . E 4
H25 H 0.4991 1.3158 0.7041 0.030 Uiso 1 1 calc R E 4
C26 C 0.5880(5) 1.3135(5) 0.5792(5) 0.0220(11) Uani 1 1 d . E 4
H26 H 0.6497 1.3989 0.6330 0.026 Uiso 1 1 calc R E 4
C27 C 0.5852(5) 1.2351(5) 0.4561(5) 0.0177(10) Uani 1 1 d . E 4
H27 H 0.6452 1.2692 0.4279 0.021 Uiso 1 1 calc R E 4


_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 O3 1.942(3) 2_675 ?
Cu1 O1 1.945(3) . ?
Cu1 N1 2.011(4) . ?
Cu1 N2 2.012(4) . ?
Cu1 O4 2.237(4) . ?
P1 O1 1.501(3) . ?
P1 O3 1.506(3) . ?
P1 O2 1.595(3) . ?
P1 C1 1.803(5) . ?
O2 C16 1.454(6) . ?
O3 Cu1 1.942(3) 2_675 ?
O5 N3 1.295(8) . ?
O5A N3A 1.260(9) . ?
O6 N3 1.236(8) . ?
O6A N3A 1.243(9) . ?
O7 N3 1.250(8) . ?
O7A N3A 1.264(9) . ?
N1 C18 1.339(6) . ?
N1 C22 1.352(6) . ?
N2 C27 1.337(6) . ?
N2 C23 1.343(6) . ?
C1 C2 1.518(7) . ?
C2 C15 1.413(7) . ?
C2 C3 1.416(7) . ?
C3 C4 1.432(7) . ?
C3 C8 1.438(7) . ?
C4 C5 1.361(7) . ?
C5 C6 1.424(8) . ?
C6 C7 1.349(8) . ?
C7 C8 1.436(7) . ?
C8 C9 1.398(7) . ?
C9 C10 1.388(7) . ?
C10 C11 1.426(7) . ?
C10 C15 1.450(7) . ?
C11 C12 1.356(8) . ?
C12 C13 1.413(8) . ?
C13 C14 1.366(7) . ?
C14 C15 1.432(7) . ?
C16 C17 1.512(7) . ?
C18 C19 1.380(7) . ?
C19 C20 1.383(8) . ?
C20 C21 1.388(8) . ?
C21 C22 1.392(7) . ?
C22 C23 1.460(7) . ?
C23 C24 1.400(7) . ?
C24 C25 1.381(8) . ?
C25 C26 1.382(8) . ?
C26 C27 1.383(7) . ?

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
O3 Cu1 O1 93.70(14) 2_675 . ?
O3 Cu1 N1 168.97(15) 2_675 . ?
O1 Cu1 N1 94.05(15) . . ?
O3 Cu1 N2 90.58(15) 2_675 . ?
O1 Cu1 N2 165.82(15) . . ?
N1 Cu1 N2 80.08(16) . . ?
O3 Cu1 O4 93.21(14) 2_675 . ?
O1 Cu1 O4 91.65(15) . . ?
N1 Cu1 O4 94.39(15) . . ?
N2 Cu1 O4 101.61(16) . . ?
O1 P1 O3 116.18(19) . . ?
O1 P1 O2 108.32(19) . . ?
O3 P1 O2 106.70(18) . . ?
O1 P1 C1 113.2(2) . . ?
O3 P1 C1 108.8(2) . . ?
O2 P1 C1 102.5(2) . . ?
P1 O1 Cu1 146.0(2) . . ?
C16 O2 P1 118.0(3) . . ?
P1 O3 Cu1 133.3(2) . 2_675 ?
C18 N1 C22 119.6(4) . . ?
C18 N1 Cu1 125.2(3) . . ?
C22 N1 Cu1 115.1(3) . . ?
C27 N2 C23 119.5(4) . . ?
C27 N2 Cu1 125.3(3) . . ?
C23 N2 Cu1 115.2(3) . . ?
O6 N3 O7 120.5(8) . . ?
O6 N3 O5 121.2(8) . . ?
O7 N3 O5 118.2(8) . . ?
O6A N3A O5A 119.7(10) . . ?
O6A N3A O7A 121.0(10) . . ?
O5A N3A O7A 118.4(10) . . ?
C2 C1 P1 118.1(3) . . ?
C15 C2 C3 119.8(4) . . ?
C15 C2 C1 120.2(4) . . ?
C3 C2 C1 120.0(4) . . ?
C2 C3 C4 122.6(5) . . ?
C2 C3 C8 119.9(4) . . ?
C4 C3 C8 117.5(4) . . ?
C5 C4 C3 120.6(5) . . ?
C4 C5 C6 121.6(5) . . ?
C7 C6 C5 119.9(5) . . ?
C6 C7 C8 120.7(5) . . ?
C9 C8 C7 120.4(5) . . ?
C9 C8 C3 120.0(4) . . ?
C7 C8 C3 119.6(5) . . ?
C10 C9 C8 120.8(5) . . ?
C9 C10 C11 120.0(5) . . ?
C9 C10 C15 120.2(4) . . ?
C11 C10 C15 119.7(5) . . ?
C12 C11 C10 120.9(5) . . ?
C11 C12 C13 119.7(5) . . ?
C14 C13 C12 122.0(5) . . ?
C13 C14 C15 120.5(5) . . ?
C2 C15 C14 123.5(5) . . ?
C2 C15 C10 119.4(4) . . ?
C14 C15 C10 117.1(4) . . ?
O2 C16 C17 108.0(4) . . ?
N1 C18 C19 121.8(5) . . ?
C18 C19 C20 119.3(5) . . ?
C19 C20 C21 119.0(5) . . ?
C20 C21 C22 119.1(5) . . ?
N1 C22 C21 121.1(5) . . ?
N1 C22 C23 114.5(4) . . ?
C21 C22 C23 124.4(5) . . ?
N2 C23 C24 121.4(5) . . ?
N2 C23 C22 114.9(4) . . ?
C24 C23 C22 123.7(5) . . ?
C25 C24 C23 119.0(5) . . ?
C24 C25 C26 118.8(5) . . ?
C25 C26 C27 119.6(5) . . ?
N2 C27 C26 121.8(5) . . ?

_diffrn_measured_fraction_theta_max 0.952
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.952
_refine_diff_density_max         0.531
_refine_diff_density_min         -1.398
_refine_diff_density_rms         0.118
