# Electronic Supplementary Material (ESI) for ChemComm.
# 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_fe02
_database_code_depnum_ccdc_archive 'CCDC 1056795'
_audit_update_record             
;
2015-03-30 deposited with the CCDC.
2015-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H36 N4 P2'
_chemical_formula_weight         394.47

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pnma

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

_cell_length_a                   9.2644(8)
_cell_length_b                   14.3849(12)
_cell_length_c                   17.7198(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2361.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1351
_cell_measurement_theta_min      3.472
_cell_measurement_theta_max      27.977

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.123
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.110
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7806
_exptl_absorpt_correction_T_max  0.8593
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6173
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2414
_reflns_number_gt                1703
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0541P)²+0.9402P] 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     SHELXL
_refine_ls_extinction_coef       0.0020(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2414
_refine_ls_number_parameters     171
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1287
_refine_ls_wR_factor_gt          0.1142
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.003

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
P1 P 1.08504(10) 0.2500 0.58241(5) 0.0414(3) Uani 1 2 d S . .
P2 P 0.89967(9) 0.2500 0.36135(4) 0.0337(2) Uani 1 2 d S . .
N1 N 0.9552(3) 0.2500 0.45551(14) 0.0330(6) Uani 1 2 d S . .
N2 N 0.8430(3) 0.2500 0.50650(14) 0.0351(6) Uani 1 2 d S . .
N3 N 0.6313(2) 0.19964(14) 0.34342(12) 0.0461(5) Uani 1 1 d . . .
C1 C 0.8942(3) 0.2500 0.57513(17) 0.0339(7) Uani 1 2 d S . .
C2 C 1.0919(3) 0.2500 0.48517(18) 0.0327(7) Uani 1 2 d S . .
C3 C 0.7537(2) 0.16336(16) 0.35954(12) 0.0363(6) Uani 1 1 d . A .
C4 C 0.7855(4) 0.2500 0.63952(19) 0.0467(9) Uani 1 2 d S . .
C5 C 0.6891(4) 0.1642(3) 0.6326(2) 0.0977(13) Uani 1 1 d . . .
H5A H 0.7469 0.1091 0.6370 0.146 Uiso 1 1 calc R . .
H5B H 0.6417 0.1646 0.5844 0.146 Uiso 1 1 calc R . .
H5C H 0.6179 0.1650 0.6720 0.146 Uiso 1 1 calc R . .
C6 C 0.8617(6) 0.2500 0.7145(2) 0.107(2) Uani 1 2 d S . .
H6A H 0.9228 0.1963 0.7179 0.160 Uiso 0.50 1 calc PR . .
H6B H 0.7917 0.2485 0.7544 0.160 Uiso 1 2 calc SR . .
H6C H 0.9192 0.3052 0.7190 0.160 Uiso 0.50 1 calc PR . .
C7 C 1.2303(4) 0.2500 0.4380(2) 0.0423(8) Uani 1 2 d S . .
C8 C 1.3603(4) 0.2500 0.4920(2) 0.0640(12) Uani 1 2 d S . .
H8A H 1.3558 0.1962 0.5240 0.096 Uiso 0.50 1 calc PR . .
H8B H 1.3580 0.3051 0.5225 0.096 Uiso 0.50 1 calc PR . .
H8C H 1.4481 0.2487 0.4633 0.096 Uiso 1 2 calc SR . .
C9 C 1.2414(3) 0.1627(2) 0.38864(19) 0.0660(9) Uani 1 1 d . . .
H9A H 1.2331 0.1083 0.4198 0.099 Uiso 1 1 calc R . .
H9B H 1.3330 0.1621 0.3633 0.099 Uiso 1 1 calc R . .
H9C H 1.1651 0.1629 0.3520 0.099 Uiso 1 1 calc R . .
C10 C 0.7725(3) 0.05898(17) 0.36491(15) 0.0472(7) Uani 1 1 d . . .
C11 C 0.8422(15) 0.0341(14) 0.4400(8) 0.070(3) Uani 0.50 1 d PU A 1
H11A H 0.7804 0.0535 0.4805 0.105 Uiso 0.50 1 calc PR A 1
H11B H 0.9336 0.0652 0.4442 0.105 Uiso 0.50 1 calc PR A 1
H11C H 0.8566 -0.0319 0.4426 0.105 Uiso 0.50 1 calc PR A 1
C12 C 0.8826(10) 0.0280(9) 0.2991(7) 0.078(3) Uani 0.50 1 d PU A 1
H12A H 0.9008 -0.0375 0.3027 0.117 Uiso 0.50 1 calc PR A 1
H12B H 0.9718 0.0614 0.3046 0.117 Uiso 0.50 1 calc PR A 1
H12C H 0.8410 0.0418 0.2508 0.117 Uiso 0.50 1 calc PR A 1
C13 C 0.6376(14) 0.0077(10) 0.3538(6) 0.088(3) Uani 0.50 1 d PU A 1
H13A H 0.6040 0.0170 0.3031 0.131 Uiso 0.50 1 calc PR A 1
H13B H 0.5662 0.0300 0.3887 0.131 Uiso 0.50 1 calc PR A 1
H13C H 0.6541 -0.0573 0.3623 0.131 Uiso 0.50 1 calc PR A 1
C11' C 0.8884(14) 0.0344(13) 0.4223(8) 0.072(4) Uani 0.50 1 d PU A 2
H11D H 0.8620 0.0589 0.4708 0.109 Uiso 0.50 1 calc PR A 2
H11E H 0.9789 0.0608 0.4068 0.109 Uiso 0.50 1 calc PR A 2
H11F H 0.8975 -0.0319 0.4256 0.109 Uiso 0.50 1 calc PR A 2
C12' C 0.8087(11) 0.0226(10) 0.2910(8) 0.092(3) Uani 0.50 1 d PU A 2
H12D H 0.8343 -0.0418 0.2953 0.138 Uiso 0.50 1 calc PR A 2
H12E H 0.8887 0.0568 0.2706 0.138 Uiso 0.50 1 calc PR A 2
H12F H 0.7270 0.0288 0.2580 0.138 Uiso 0.50 1 calc PR A 2
C13' C 0.6238(14) 0.0158(9) 0.3916(6) 0.082(3) Uani 0.50 1 d PU A 2
H13D H 0.5480 0.0364 0.3587 0.123 Uiso 0.50 1 calc PR A 2
H13E H 0.6036 0.0355 0.4423 0.123 Uiso 0.50 1 calc PR A 2
H13F H 0.6297 -0.0508 0.3900 0.123 Uiso 0.50 1 calc PR A 2


_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 C2 1.724(3) . ?
P1 C1 1.773(3) . ?
P2 N1 1.746(3) . ?
P2 C3 1.839(2) 8_565 ?
P2 C3 1.839(2) . ?
N1 C2 1.371(4) . ?
N1 N2 1.377(3) . ?
N2 C1 1.305(4) . ?
N3 C3 1.281(3) . ?
N3 N3 1.449(4) 8_565 ?
C1 C4 1.522(4) . ?
C2 C7 1.531(4) . ?
C3 C10 1.515(4) . ?
C4 C6 1.504(6) . ?
C4 C5 1.529(4) 8_565 ?
C4 C5 1.529(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9601 . ?
C6 H6B 0.9601 . ?
C6 H6C 0.9601 . ?
C7 C9 1.534(3) 8_565 ?
C7 C9 1.534(3) . ?
C7 C8 1.538(5) . ?
C8 H8A 0.9601 . ?
C8 H8B 0.9601 . ?
C8 H8C 0.9601 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C12' 1.450(13) . ?
C10 C13 1.464(13) . ?
C10 C11' 1.521(15) . ?
C10 C11 1.521(15) . ?
C10 C13' 1.583(13) . ?
C10 C12 1.612(12) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C11' H11D 0.9600 . ?
C11' H11E 0.9600 . ?
C11' H11F 0.9600 . ?
C12' H12D 0.9600 . ?
C12' H12E 0.9600 . ?
C12' H12F 0.9600 . ?
C13' H13D 0.9600 . ?
C13' H13E 0.9600 . ?
C13' H13F 0.9600 . ?

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
C2 P1 C1 87.93(15) . . ?
N1 P2 C3 103.50(10) . 8_565 ?
N1 P2 C3 103.50(10) . . ?
C3 P2 C3 85.32(15) 8_565 . ?
C2 N1 N2 116.5(3) . . ?
C2 N1 P2 129.7(2) . . ?
N2 N1 P2 113.85(19) . . ?
C1 N2 N1 109.7(3) . . ?
C3 N3 N3 114.04(13) . 8_565 ?
N2 C1 C4 117.3(3) . . ?
N2 C1 P1 115.5(2) . . ?
C4 C1 P1 127.2(2) . . ?
N1 C2 C7 124.4(3) . . ?
N1 C2 P1 110.4(2) . . ?
C7 C2 P1 125.2(2) . . ?
N3 C3 C10 121.3(2) . . ?
N3 C3 P2 112.27(17) . . ?
C10 C3 P2 125.90(18) . . ?
C6 C4 C1 110.6(3) . . ?
C6 C4 C5 110.2(2) . 8_565 ?
C1 C4 C5 109.1(2) . 8_565 ?
C6 C4 C5 110.2(2) . . ?
C1 C4 C5 109.1(2) . . ?
C5 C4 C5 107.7(4) 8_565 . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 C9 111.55(19) . 8_565 ?
C2 C7 C9 111.55(19) . . ?
C9 C7 C9 109.9(4) 8_565 . ?
C2 C7 C8 108.4(3) . . ?
C9 C7 C8 107.6(2) 8_565 . ?
C9 C7 C8 107.6(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
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 . . ?
C12' C10 C13 83.9(6) . . ?
C12' C10 C3 109.1(6) . . ?
C13 C10 C3 113.1(6) . . ?
C12' C10 C11' 110.9(8) . . ?
C13 C10 C11' 125.2(8) . . ?
C3 C10 C11' 110.7(7) . . ?
C12' C10 C11 127.4(8) . . ?
C13 C10 C11 111.2(8) . . ?
C3 C10 C11 109.7(7) . . ?
C11' C10 C11 20.1(8) . . ?
C12' C10 C13' 109.3(6) . . ?
C13 C10 C13' 25.9(6) . . ?
C3 C10 C13' 107.9(5) . . ?
C11' C10 C13' 108.9(7) . . ?
C11 C10 C13' 90.9(7) . . ?
C12' C10 C12 25.9(6) . . ?
C13 C10 C12 107.7(6) . . ?
C3 C10 C12 107.5(5) . . ?
C11' C10 C12 88.4(7) . . ?
C11 C10 C12 107.4(7) . . ?
C13' C10 C12 131.2(6) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
C10 C11' H11D 109.5 . . ?
C10 C11' H11E 109.5 . . ?
H11D C11' H11E 109.5 . . ?
C10 C11' H11F 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?
C10 C12' H12D 109.5 . . ?
C10 C12' H12E 109.5 . . ?
H12D C12' H12E 109.5 . . ?
C10 C12' H12F 109.5 . . ?
H12D C12' H12F 109.5 . . ?
H12E C12' H12F 109.5 . . ?
C10 C13' H13D 109.5 . . ?
C10 C13' H13E 109.5 . . ?
H13D C13' H13E 109.5 . . ?
C10 C13' H13F 109.5 . . ?
H13D C13' H13F 109.5 . . ?
H13E C13' H13F 109.5 . . ?

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
C3 P2 N1 C2 -135.82(8) 8_565 . . . ?
C3 P2 N1 C2 135.82(8) . . . . ?
C3 P2 N1 N2 44.18(8) 8_565 . . . ?
C3 P2 N1 N2 -44.18(8) . . . . ?
C2 N1 N2 C1 0.0 . . . . ?
P2 N1 N2 C1 180.0 . . . . ?
N1 N2 C1 C4 180.0 . . . . ?
N1 N2 C1 P1 0.0 . . . . ?
C2 P1 C1 N2 0.0 . . . . ?
C2 P1 C1 C4 180.0 . . . . ?
N2 N1 C2 C7 180.0 . . . . ?
P2 N1 C2 C7 0.0 . . . . ?
N2 N1 C2 P1 0.0 . . . . ?
P2 N1 C2 P1 180.0 . . . . ?
C1 P1 C2 N1 0.0 . . . . ?
C1 P1 C2 C7 180.0 . . . . ?
N3 N3 C3 C10 177.79(17) 8_565 . . . ?
N3 N3 C3 P2 -10.12(18) 8_565 . . . ?
N1 P2 C3 N3 115.38(18) . . . . ?
C3 P2 C3 N3 12.6(2) 8_565 . . . ?
N1 P2 C3 C10 -73.0(2) . . . . ?
C3 P2 C3 C10 -175.75(15) 8_565 . . . ?
N2 C1 C4 C6 180.000(1) . . . . ?
P1 C1 C4 C6 0.000(1) . . . . ?
N2 C1 C4 C5 -58.7(3) . . . 8_565 ?
P1 C1 C4 C5 121.3(3) . . . 8_565 ?
N2 C1 C4 C5 58.7(3) . . . . ?
P1 C1 C4 C5 -121.3(3) . . . . ?
N1 C2 C7 C9 61.7(2) . . . 8_565 ?
P1 C2 C7 C9 -118.3(2) . . . 8_565 ?
N1 C2 C7 C9 -61.7(2) . . . . ?
P1 C2 C7 C9 118.3(2) . . . . ?
N1 C2 C7 C8 180.0 . . . . ?
P1 C2 C7 C8 0.0 . . . . ?
N3 C3 C10 C12' 88.6(5) . . . . ?
P2 C3 C10 C12' -82.4(5) . . . . ?
N3 C3 C10 C13 -2.9(6) . . . . ?
P2 C3 C10 C13 -173.8(5) . . . . ?
N3 C3 C10 C11' -149.1(6) . . . . ?
P2 C3 C10 C11' 40.0(6) . . . . ?
N3 C3 C10 C11 -127.7(6) . . . . ?
P2 C3 C10 C11 61.4(6) . . . . ?
N3 C3 C10 C13' -30.0(5) . . . . ?
P2 C3 C10 C13' 159.0(4) . . . . ?
N3 C3 C10 C12 115.9(5) . . . . ?
P2 C3 C10 C12 -55.1(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.047
