# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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. 
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data_NapC602_0m
_database_code_depnum_ccdc_archive 'CCDC 1060816'
_audit_update_record             
;
2015-04-21 deposited with the CCDC.
2015-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C144 H42 O6 P2'
_chemical_formula_weight         1929.71

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'
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'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   19.058(12)
_cell_length_b                   19.058(12)
_cell_length_c                   20.787(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     6539(9)
_cell_formula_units_Z            3
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1646
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      25.65

_exptl_crystal_description       cubic
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_F_000             2952
_exptl_transmission_factor_min   0.994
_exptl_transmission_factor_max   0.994
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.124
_shelx_estimated_absorpt_T_min   0.994
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11604
_diffrn_reflns_av_unetI/netI     0.0926
_diffrn_reflns_av_R_equivalents  0.1014
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.575
_diffrn_reflns_theta_max         26.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3025
_reflns_number_gt                1830
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0527P)²+3.7332P] 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         3025
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1401
_refine_ls_wR_factor_gt          0.1117
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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 1.0000 0.0000 0.12045(6) 0.0359(3) Uani 1 3 d S T P . .
O1 O 1.16455(11) 0.05103(11) 0.17821(9) 0.0373(5) Uani 1 1 d . . . . .
C1 C 0.88496(15) -0.17955(15) 0.40916(13) 0.0301(6) Uani 1 1 d . . . . .
C2 C 0.80874(15) -0.10743(15) 0.42270(13) 0.0303(6) Uani 1 1 d . . . . .
C3 C 0.85580(15) -0.12768(15) 0.38411(12) 0.0294(6) Uani 1 1 d . . . . .
C4 C 0.96603(16) -0.15050(15) 0.38405(12) 0.0294(6) Uani 1 1 d . . . . .
C5 C 0.82292(15) -0.02484(16) 0.42259(13) 0.0303(6) Uani 1 1 d . . . . .
C6 C 1.01567(16) 0.29381(16) 0.27077(14) 0.0351(7) Uani 1 1 d . . . . .
C7 C 1.07858(16) 0.20914(16) 0.22377(13) 0.0332(6) Uani 1 1 d . . . . .
C8 C 1.18780(16) 0.17718(16) 0.22323(14) 0.0349(7) Uani 1 1 d . . . . .
H1 H 1.2409 0.1900 0.2357 0.042 Uiso 1 1 calc R U . . .
C9 C 0.91892(15) -0.06607(15) 0.34378(11) 0.0285(6) Uani 1 1 d . . . . .
C10 C 0.98723(16) -0.08022(16) 0.34385(12) 0.0295(6) Uani 1 1 d . . . . .
C11 C 1.13781(16) 0.10663(16) 0.18945(13) 0.0320(6) Uani 1 1 d . . . . .
C12 C 1.03047(16) 0.13745(16) 0.18935(13) 0.0335(7) Uani 1 1 d . . . . .
C13 C 0.78875(14) -0.13867(15) 0.48797(13) 0.0315(6) Uani 1 1 d . . . . .
C14 C 1.15806(16) 0.22866(17) 0.23836(14) 0.0362(7) Uani 1 1 d . . . . .
H2 H 1.1928 0.2786 0.2593 0.043 Uiso 1 1 calc R U . . .
C15 C 0.96873(16) 0.33241(16) 0.36711(14) 0.0374(7) Uani 1 1 d . . . . .
H3 H 0.9840 0.3007 0.3924 0.045 Uiso 1 1 calc R U . . .
C16 C 0.86568(15) -0.20965(14) 0.47160(13) 0.0298(6) Uani 1 1 d . . . . .
C17 C 0.95644(16) 0.38295(17) 0.26400(15) 0.0397(7) Uani 1 1 d . . . . .
H4 H 0.9634 0.3862 0.2186 0.048 Uiso 1 1 calc R U . . .
C18 C 1.04498(16) 0.25677(16) 0.24760(14) 0.0360(7) Uani 1 1 d . . . . .
C19 C 0.81152(15) -0.00523(16) 0.48806(13) 0.0308(6) Uani 1 1 d . . . . .
C20 C 1.06213(16) 0.08986(16) 0.16798(13) 0.0334(7) Uani 1 1 d . . . . .
C21 C 0.98027(15) 0.33663(15) 0.30062(14) 0.0329(6) Uani 1 1 d . . . . .
C22 C 0.93539(17) 0.37383(18) 0.39648(16) 0.0460(8) Uani 1 1 d . . . . .
H5 H 0.9281 0.3708 0.4418 0.055 Uiso 1 1 calc R U . . .
C23 C 0.91254(18) 0.41960(19) 0.36014(19) 0.0525(9) Uani 1 1 d . . . . .
H6 H 0.8897 0.4483 0.3805 0.063 Uiso 1 1 calc R U . . .
C24 C 0.92281(18) 0.42380(18) 0.29407(18) 0.0510(9) Uani 1 1 d . . . . .
H7 H 0.9066 0.4551 0.2692 0.061 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 C20 1.812(3) 2_645 ?
P1 C20 1.812(3) . ?
P1 C20 1.812(3) 3_765 ?
O1 C12 1.402(3) 3_765 ?
O1 C11 1.406(3) . ?
C1 C16 1.392(4) . ?
C1 C3 1.451(4) . ?
C1 C4 1.453(4) . ?
C2 C3 1.394(4) . ?
C2 C13 1.454(4) . ?
C2 C5 1.458(4) . ?
C3 C9 1.455(4) . ?
C4 C5 1.392(4) 2_645 ?
C4 C10 1.454(4) . ?
C5 C4 1.391(4) 3_765 ?
C5 C19 1.456(4) . ?
C6 C18 1.199(4) . ?
C6 C21 1.434(4) . ?
C7 C14 1.401(4) . ?
C7 C12 1.402(4) . ?
C7 C18 1.436(4) . ?
C8 C11 1.388(4) . ?
C8 C14 1.393(4) . ?
C8 H1 0.9500 . ?
C9 C10 1.391(4) 3_765 ?
C9 C10 1.456(4) . ?
C10 C9 1.391(4) 2_645 ?
C11 C20 1.386(4) . ?
C12 C20 1.390(4) . ?
C12 O1 1.402(3) 2_645 ?
C13 C19 1.393(4) 12_546 ?
C13 C16 1.459(4) 11_666 ?
C14 H2 0.9500 . ?
C15 C22 1.379(4) . ?
C15 C21 1.396(4) . ?
C15 H3 0.9500 . ?
C16 C19 1.453(4) 12_546 ?
C16 C13 1.459(4) 12_546 ?
C17 C24 1.381(4) . ?
C17 C21 1.402(4) . ?
C17 H4 0.9500 . ?
C19 C13 1.393(4) 11_666 ?
C19 C16 1.453(4) 11_666 ?
C22 C23 1.379(4) . ?
C22 H5 0.9500 . ?
C23 C24 1.384(5) . ?
C23 H6 0.9500 . ?
C24 H7 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
C20 P1 C20 93.10(13) 2_645 . ?
C20 P1 C20 93.09(13) 2_645 3_765 ?
C20 P1 C20 93.10(13) . 3_765 ?
C12 O1 C11 115.45(18) 3_765 . ?
C16 C1 C3 120.2(2) . . ?
C16 C1 C4 120.2(2) . . ?
C3 C1 C4 107.9(2) . . ?
C3 C2 C13 119.8(2) . . ?
C3 C2 C5 120.0(2) . . ?
C13 C2 C5 108.2(2) . . ?
C2 C3 C1 120.0(2) . . ?
C2 C3 C9 119.7(2) . . ?
C1 C3 C9 108.2(2) . . ?
C5 C4 C1 120.0(2) 2_645 . ?
C5 C4 C10 119.8(2) 2_645 . ?
C1 C4 C10 108.1(2) . . ?
C4 C5 C19 120.1(2) 3_765 . ?
C4 C5 C2 120.1(2) 3_765 . ?
C19 C5 C2 107.7(2) . . ?
C18 C6 C21 177.9(3) . . ?
C14 C7 C12 117.6(2) . . ?
C14 C7 C18 121.5(2) . . ?
C12 C7 C18 120.7(2) . . ?
C11 C8 C14 118.2(3) . . ?
C11 C8 H1 120.9 . . ?
C14 C8 H1 120.9 . . ?
C10 C9 C3 120.2(2) 3_765 . ?
C10 C9 C10 119.9(3) 3_765 . ?
C3 C9 C10 107.8(2) . . ?
C9 C10 C4 120.1(2) 2_645 . ?
C9 C10 C9 120.1(3) 2_645 . ?
C4 C10 C9 108.0(2) . . ?
C20 C11 C8 121.1(2) . . ?
C20 C11 O1 120.0(2) . . ?
C8 C11 O1 118.8(2) . . ?
C20 C12 O1 120.4(2) . 2_645 ?
C20 C12 C7 120.9(2) . . ?
O1 C12 C7 118.7(2) 2_645 . ?
C19 C13 C2 120.1(2) 12_546 . ?
C19 C13 C16 120.1(2) 12_546 11_666 ?
C2 C13 C16 107.8(2) . 11_666 ?
C8 C14 C7 122.1(3) . . ?
C8 C14 H2 119.0 . . ?
C7 C14 H2 119.0 . . ?
C22 C15 C21 120.7(3) . . ?
C22 C15 H3 119.7 . . ?
C21 C15 H3 119.7 . . ?
C1 C16 C19 119.8(2) . 12_546 ?
C1 C16 C13 119.8(2) . 12_546 ?
C19 C16 C13 108.0(2) 12_546 12_546 ?
C24 C17 C21 119.8(3) . . ?
C24 C17 H4 120.1 . . ?
C21 C17 H4 120.1 . . ?
C6 C18 C7 176.1(3) . . ?
C13 C19 C16 120.0(2) 11_666 11_666 ?
C13 C19 C5 119.9(2) 11_666 . ?
C16 C19 C5 108.2(2) 11_666 . ?
C11 C20 C12 119.2(2) . . ?
C11 C20 P1 120.4(2) . . ?
C12 C20 P1 120.0(2) . . ?
C15 C21 C17 118.9(3) . . ?
C15 C21 C6 120.1(3) . . ?
C17 C21 C6 121.1(3) . . ?
C23 C22 C15 120.1(3) . . ?
C23 C22 H5 120.0 . . ?
C15 C22 H5 120.0 . . ?
C22 C23 C24 120.0(3) . . ?
C22 C23 H6 120.0 . . ?
C24 C23 H6 120.0 . . ?
C17 C24 C23 120.6(3) . . ?
C17 C24 H7 119.7 . . ?
C23 C24 H7 119.7 . . ?

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
C13 C2 C3 C1 -0.2(4) . . . . ?
C5 C2 C3 C1 138.1(2) . . . . ?
C13 C2 C3 C9 -138.4(2) . . . . ?
C5 C2 C3 C9 -0.1(4) . . . . ?
C16 C1 C3 C2 0.4(4) . . . . ?
C4 C1 C3 C2 -142.8(2) . . . . ?
C16 C1 C3 C9 142.8(2) . . . . ?
C4 C1 C3 C9 -0.4(3) . . . . ?
C16 C1 C4 C5 -0.4(4) . . . 2_645 ?
C3 C1 C4 C5 142.8(2) . . . 2_645 ?
C16 C1 C4 C10 -142.7(2) . . . . ?
C3 C1 C4 C10 0.4(3) . . . . ?
C3 C2 C5 C4 -0.1(4) . . . 3_765 ?
C13 C2 C5 C4 142.5(2) . . . 3_765 ?
C3 C2 C5 C19 -142.7(2) . . . . ?
C13 C2 C5 C19 0.0(3) . . . . ?
C2 C3 C9 C10 0.3(4) . . . 3_765 ?
C1 C3 C9 C10 -142.3(2) . . . 3_765 ?
C2 C3 C9 C10 142.7(2) . . . . ?
C1 C3 C9 C10 0.2(3) . . . . ?
C5 C4 C10 C9 0.2(4) 2_645 . . 2_645 ?
C1 C4 C10 C9 142.6(2) . . . 2_645 ?
C5 C4 C10 C9 -142.8(2) 2_645 . . . ?
C1 C4 C10 C9 -0.3(3) . . . . ?
C10 C9 C10 C9 -0.2(5) 3_765 . . 2_645 ?
C3 C9 C10 C9 -142.8(2) . . . 2_645 ?
C10 C9 C10 C4 142.7(2) 3_765 . . . ?
C3 C9 C10 C4 0.1(3) . . . . ?
C14 C8 C11 C20 3.7(4) . . . . ?
C14 C8 C11 O1 -175.1(2) . . . . ?
C12 O1 C11 C20 -43.7(3) 3_765 . . . ?
C12 O1 C11 C8 135.1(3) 3_765 . . . ?
C14 C7 C12 C20 -3.0(4) . . . . ?
C18 C7 C12 C20 -177.9(2) . . . . ?
C14 C7 C12 O1 175.4(2) . . . 2_645 ?
C18 C7 C12 O1 0.5(4) . . . 2_645 ?
C3 C2 C13 C19 0.2(4) . . . 12_546 ?
C5 C2 C13 C19 -142.5(2) . . . 12_546 ?
C3 C2 C13 C16 142.8(2) . . . 11_666 ?
C5 C2 C13 C16 0.1(3) . . . 11_666 ?
C11 C8 C14 C7 3.6(4) . . . . ?
C12 C7 C14 C8 -3.9(4) . . . . ?
C18 C7 C14 C8 170.9(3) . . . . ?
C3 C1 C16 C19 -0.5(4) . . . 12_546 ?
C4 C1 C16 C19 138.2(2) . . . 12_546 ?
C3 C1 C16 C13 -138.2(2) . . . 12_546 ?
C4 C1 C16 C13 0.6(4) . . . 12_546 ?
C4 C5 C19 C13 0.1(4) 3_765 . . 11_666 ?
C2 C5 C19 C13 142.7(2) . . . 11_666 ?
C4 C5 C19 C16 -142.7(2) 3_765 . . 11_666 ?
C2 C5 C19 C16 0.0(3) . . . 11_666 ?
C8 C11 C20 C12 -10.5(4) . . . . ?
O1 C11 C20 C12 168.3(2) . . . . ?
C8 C11 C20 P1 176.8(2) . . . . ?
O1 C11 C20 P1 -4.4(3) . . . . ?
O1 C12 C20 C11 -168.3(2) 2_645 . . . ?
C7 C12 C20 C11 10.1(4) . . . . ?
O1 C12 C20 P1 4.4(3) 2_645 . . . ?
C7 C12 C20 P1 -177.2(2) . . . . ?
C20 P1 C20 C11 132.99(17) 2_645 . . . ?
C20 P1 C20 C11 39.7(3) 3_765 . . . ?
C20 P1 C20 C12 -39.6(3) 2_645 . . . ?
C20 P1 C20 C12 -132.89(17) 3_765 . . . ?
C22 C15 C21 C17 -0.8(4) . . . . ?
C22 C15 C21 C6 179.5(2) . . . . ?
C24 C17 C21 C15 0.5(4) . . . . ?
C24 C17 C21 C6 -179.7(3) . . . . ?
C21 C15 C22 C23 0.4(4) . . . . ?
C15 C22 C23 C24 0.2(4) . . . . ?
C21 C17 C24 C23 0.1(4) . . . . ?
C22 C23 C24 C17 -0.5(5) . . . . ?

_refine_diff_density_max         0.233
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.051

_shelxl_version_number           2014-3



