# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1485237'
_audit_update_record             
;
2016-06-13 deposited with the CCDC.
2016-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H22 Cl8 N10 P6'
_chemical_formula_sum            'C14 H22 Cl8 N10 P6'
_chemical_formula_weight         799.84

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.4119(4)
_cell_length_b                   33.4898(13)
_cell_length_c                   10.4590(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.3160(10)
_cell_angle_gamma                90
_cell_volume                     3269.9(2)
_cell_formula_units_Z            5
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9797
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      30.33

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_F_000             1608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.010
_shelx_estimated_absorpt_T_min   0.632
_shelx_estimated_absorpt_T_max   0.824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.661
_exptl_absorpt_correction_T_max  0.817
_exptl_absorpt_process_details   'SADABS; Bruker, 2005'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15322
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       46
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.744
_diffrn_reflns_theta_max         30.301
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measured_fraction_theta_full 0.935
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_Laue_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_point_group_measured_fraction_full 0.935
_reflns_number_total             8440
_reflns_number_gt                5917
_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-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Ortep-3 for Windows (Farrugia, 1997)'

_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)+(0.0492P)²+3.5909P] 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         8440
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1405
_refine_ls_wR_factor_gt          0.1293
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
Cl1 Cl 1.11248(11) 0.05333(4) 0.01218(12) 0.0749(3) Uani 1 1 d . . . . .
Cl2 Cl 0.91948(14) 0.11540(3) -0.14091(10) 0.0730(3) Uani 1 1 d . . . . .
Cl3 Cl 0.69922(12) 0.00845(3) 0.21951(11) 0.0714(3) Uani 1 1 d . . . . .
Cl4 Cl 0.49933(10) 0.05811(4) 0.02669(11) 0.0739(3) Uani 1 1 d . . . . .
Cl5 Cl 0.73508(11) 0.20833(4) 0.75761(13) 0.0795(3) Uani 1 1 d . . . . .
Cl6 Cl 0.54219(15) 0.25937(4) 0.56453(13) 0.0863(4) Uani 1 1 d . . . . .
Cl7 Cl 0.11790(10) 0.20718(3) 0.74878(11) 0.0691(3) Uani 1 1 d . . . . .
Cl8 Cl 0.31746(16) 0.15416(4) 0.92972(12) 0.0929(4) Uani 1 1 d . . . . .
P1 P 0.84962(9) 0.12454(2) 0.23813(8) 0.04066(19) Uani 1 1 d . . . . .
P2 P 0.69792(8) 0.05979(2) 0.11993(8) 0.03954(18) Uani 1 1 d . . . . .
P3 P 0.93616(9) 0.08509(3) 0.02502(8) 0.04182(19) Uani 1 1 d . . . . .
P4 P 0.39748(8) 0.14057(3) 0.54085(9) 0.0468(2) Uani 1 1 d . . . . .
P5 P 0.30512(9) 0.17868(3) 0.75431(9) 0.0456(2) Uani 1 1 d . . . . .
P6 P 0.53880(9) 0.20738(3) 0.65799(9) 0.0457(2) Uani 1 1 d . . . . .
N1 N 0.7111(3) 0.09599(9) 0.2141(3) 0.0479(7) Uani 1 1 d . . . . .
N2 N 0.8070(3) 0.05473(9) 0.0185(3) 0.0543(8) Uani 1 1 d . . . . .
N3 N 0.9647(3) 0.11443(9) 0.1410(3) 0.0519(7) Uani 1 1 d . . . . .
N4 N 0.2912(3) 0.14585(9) 0.6491(3) 0.0568(8) Uani 1 1 d . . . . .
N5 N 0.4271(3) 0.21120(10) 0.7573(3) 0.0586(8) Uani 1 1 d . . . . .
N6 N 0.5275(3) 0.17212(9) 0.5606(3) 0.0562(8) Uani 1 1 d . . . . .
N7 N 0.8064(4) 0.17175(9) 0.2343(3) 0.0626(8) Uani 1 1 d . . . . .
N8 N 0.9216(3) 0.12462(9) 0.3875(3) 0.0496(7) Uani 1 1 d . . . . .
N9 N 0.4561(3) 0.09537(9) 0.5332(3) 0.0559(8) Uani 1 1 d . . . . .
N10 N 0.3098(3) 0.14104(11) 0.3946(3) 0.0647(9) Uani 1 1 d . . . . .
C1 C 0.8745(6) 0.01640(13) 0.6918(4) 0.0740(12) Uani 1 1 d . . . . .
H1 H 0.9147 -0.0049 0.7406 0.089 Uiso 1 1 calc R U . . .
C2 C 0.9543(5) 0.03680(13) 0.6126(4) 0.0663(11) Uani 1 1 d . . . . .
H2 H 1.0485 0.0292 0.6082 0.080 Uiso 1 1 calc R U . . .
C3 C 0.8971(4) 0.06843(11) 0.5394(3) 0.0474(8) Uani 1 1 d . . . . .
C4 C 0.7565(3) 0.07915(10) 0.5479(3) 0.0466(7) Uani 1 1 d . . . . .
H4 H 0.7159 0.1003 0.4985 0.056 Uiso 1 1 calc R U . . .
C5 C 0.6751(4) 0.05904(10) 0.6286(3) 0.0505(8) Uani 1 1 d . . . . .
C6 C 0.7351(5) 0.02737(11) 0.6996(4) 0.0638(10) Uani 1 1 d . . . . .
H6 H 0.6811 0.0133 0.7531 0.077 Uiso 1 1 calc R U . . .
C7 C 0.9889(4) 0.09039(13) 0.4539(4) 0.0594(10) Uani 1 1 d . . . . .
H7A H 1.0758 0.0992 0.5063 0.071 Uiso 1 1 calc R U . . .
H7B H 1.0165 0.0718 0.3903 0.071 Uiso 1 1 calc R U . . .
C8 C 0.5234(4) 0.07307(12) 0.6410(4) 0.0674(12) Uani 1 1 d . . . . .
H8A H 0.4648 0.0499 0.6531 0.081 Uiso 1 1 calc R U . . .
H8B H 0.5261 0.0895 0.7177 0.081 Uiso 1 1 calc R U . . .
C9 C 0.4031(4) 0.07544(14) 0.4116(5) 0.0781(14) Uani 1 1 d . . . . .
H9A H 0.3244 0.0577 0.4233 0.094 Uiso 1 1 calc R U . . .
H9B H 0.4788 0.0600 0.3805 0.094 Uiso 1 1 calc R U . . .
C10 C 0.3539(5) 0.10777(18) 0.3185(5) 0.0864(16) Uani 1 1 d . . . . .
H10A H 0.4310 0.1159 0.2709 0.104 Uiso 1 1 calc R U . . .
H10B H 0.2741 0.0986 0.2577 0.104 Uiso 1 1 calc R U . . .
C11 C 0.2694(6) 0.17769(18) 0.3266(5) 0.0936(16) Uani 1 1 d . . . . .
H11A H 0.2469 0.1976 0.3869 0.140 Uiso 1 1 calc R U . . .
H11B H 0.1871 0.1730 0.2643 0.140 Uiso 1 1 calc R U . . .
H11C H 0.3475 0.1868 0.2834 0.140 Uiso 1 1 calc R U . . .
C12 C 0.9126(5) 0.16315(13) 0.4511(4) 0.0660(11) Uani 1 1 d . . . . .
H12A H 1.0066 0.1754 0.4673 0.079 Uiso 1 1 calc R U . . .
H12B H 0.8752 0.1598 0.5327 0.079 Uiso 1 1 calc R U . . .
C13 C 0.8141(5) 0.18861(12) 0.3620(4) 0.0720(12) Uani 1 1 d . . . . .
H13A H 0.7196 0.1891 0.3897 0.086 Uiso 1 1 calc R U . . .
H13B H 0.8502 0.2157 0.3621 0.086 Uiso 1 1 calc R U . . .
C14 C 0.7062(6) 0.18801(14) 0.1309(5) 0.0833(14) Uani 1 1 d . . . . .
H14A H 0.7124 0.1732 0.0533 0.125 Uiso 1 1 calc R U . . .
H14B H 0.7290 0.2155 0.1175 0.125 Uiso 1 1 calc R U . . .
H14C H 0.6107 0.1861 0.1534 0.125 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 N1 1.610(3) . ?
P1 N3 1.613(3) . ?
P1 N7 1.632(3) . ?
P1 N8 1.622(3) . ?
P2 Cl3 2.0095(13) . ?
P2 Cl4 1.9959(12) . ?
P2 N1 1.557(3) . ?
P2 N2 1.576(3) . ?
P3 Cl1 1.9900(13) . ?
P3 Cl2 1.9994(13) . ?
P3 N2 1.580(3) . ?
P3 N3 1.557(3) . ?
P4 N4 1.613(3) . ?
P4 N6 1.610(3) . ?
P4 N9 1.616(3) . ?
P4 N10 1.643(4) . ?
P5 Cl7 1.9983(13) . ?
P5 Cl8 1.9997(15) . ?
P5 N4 1.549(3) . ?
P5 N5 1.580(3) . ?
P6 Cl5 2.0023(13) . ?
P6 Cl6 1.9989(15) . ?
P6 N5 1.574(3) . ?
P6 N6 1.554(3) . ?
N7 C13 1.443(5) . ?
N7 C14 1.448(6) . ?
N8 C7 1.444(5) . ?
N8 C12 1.459(5) . ?
N9 C8 1.432(5) . ?
N9 C9 1.467(5) . ?
N10 C10 1.459(5) . ?
N10 C11 1.445(6) . ?
C1 C2 1.370(6) . ?
C1 C6 1.375(6) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 C2 1.375(5) . ?
C3 C7 1.511(5) . ?
C4 C3 1.385(4) . ?
C4 H4 0.9300 . ?
C5 C4 1.385(4) . ?
C5 C6 1.374(5) . ?
C5 C8 1.524(5) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.489(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.495(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
N1 P1 N3 111.86(14) . . ?
N1 P1 N7 112.17(17) . . ?
N1 P1 N8 112.43(15) . . ?
N3 P1 N7 111.91(17) . . ?
N3 P1 N8 112.07(16) . . ?
N8 P1 N7 95.42(17) . . ?
Cl4 P2 Cl3 99.94(6) . . ?
N1 P2 Cl3 110.09(13) . . ?
N1 P2 Cl4 109.00(12) . . ?
N1 P2 N2 120.20(14) . . ?
N2 P2 Cl3 107.17(13) . . ?
N2 P2 Cl4 108.54(13) . . ?
Cl1 P3 Cl2 100.76(6) . . ?
N2 P3 Cl1 107.26(13) . . ?
N2 P3 Cl2 108.34(13) . . ?
N3 P3 Cl1 109.10(13) . . ?
N3 P3 Cl2 110.02(13) . . ?
N3 P3 N2 119.66(14) . . ?
N4 P4 N9 112.56(17) . . ?
N4 P4 N10 111.69(17) . . ?
N6 P4 N4 111.55(14) . . ?
N6 P4 N9 111.24(16) . . ?
N6 P4 N10 113.35(18) . . ?
N9 P4 N10 95.55(18) . . ?
Cl7 P5 Cl8 99.83(6) . . ?
N4 P5 N5 119.90(15) . . ?
N4 P5 Cl7 108.90(13) . . ?
N4 P5 Cl8 110.50(14) . . ?
N5 P5 Cl7 107.89(13) . . ?
N5 P5 Cl8 107.93(14) . . ?
Cl6 P6 Cl5 99.76(7) . . ?
N5 P6 Cl5 107.75(13) . . ?
N5 P6 Cl6 107.78(14) . . ?
N6 P6 Cl5 109.55(13) . . ?
N6 P6 Cl6 110.20(14) . . ?
N6 P6 N5 119.90(15) . . ?
P2 N1 P1 123.97(16) . . ?
P2 N2 P3 117.74(17) . . ?
P3 N3 P1 124.07(17) . . ?
P5 N4 P4 124.92(17) . . ?
P6 N5 P5 118.42(18) . . ?
P6 N6 P4 124.75(17) . . ?
C13 N7 P1 111.9(3) . . ?
C13 N7 C14 119.7(4) . . ?
C14 N7 P1 121.3(3) . . ?
C7 N8 P1 124.5(2) . . ?
C7 N8 C12 122.0(3) . . ?
C12 N8 P1 113.5(3) . . ?
C8 N9 P4 124.7(3) . . ?
C8 N9 C9 120.9(4) . . ?
C9 N9 P4 112.9(3) . . ?
C10 N10 P4 110.9(3) . . ?
C11 N10 P4 122.4(3) . . ?
C11 N10 C10 117.1(4) . . ?
C2 C1 C6 120.2(4) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C1 C2 C3 121.0(4) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 118.2(4) . . ?
C2 C3 C7 119.4(3) . . ?
C4 C3 C7 122.3(3) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.4(3) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C8 120.0(3) . . ?
C6 C5 C4 118.9(4) . . ?
C6 C5 C8 121.1(3) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.3(4) . . ?
C5 C6 H6 119.9 . . ?
C3 C7 H7A 108.5 . . ?
C3 C7 H7B 108.5 . . ?
N8 C7 C3 115.0(3) . . ?
N8 C7 H7A 108.5 . . ?
N8 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
N9 C8 C5 114.7(3) . . ?
N9 C8 H8A 108.6 . . ?
N9 C8 H8B 108.6 . . ?
C5 C8 H8A 108.6 . . ?
C5 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
N9 C9 C10 106.2(3) . . ?
N9 C9 H9A 110.5 . . ?
N9 C9 H9B 110.5 . . ?
C10 C9 H9A 110.5 . . ?
C10 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
N10 C10 C9 106.6(4) . . ?
N10 C10 H10A 110.4 . . ?
N10 C10 H10B 110.4 . . ?
C9 C10 H10A 110.4 . . ?
C9 C10 H10B 110.4 . . ?
H10A C10 H10B 108.6 . . ?
N10 C11 H11A 109.5 . . ?
N10 C11 H11B 109.5 . . ?
N10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N8 C12 C13 106.7(3) . . ?
N8 C12 H12A 110.4 . . ?
N8 C12 H12B 110.4 . . ?
C13 C12 H12A 110.4 . . ?
C13 C12 H12B 110.4 . . ?
H12A C12 H12B 108.6 . . ?
N7 C14 H14A 109.5 . . ?
N7 C14 H14B 109.5 . . ?
N7 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N7 C13 C12 107.9(3) . . ?
N7 C13 H13A 110.1 . . ?
N7 C13 H13B 110.1 . . ?
C12 C13 H13A 110.1 . . ?
C12 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?

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
N3 P1 N1 P2 6.8(3) . . . . ?
N7 P1 N1 P2 133.5(2) . . . . ?
N8 P1 N1 P2 -120.4(2) . . . . ?
N1 P1 N3 P3 8.5(3) . . . . ?
N7 P1 N3 P3 -118.4(3) . . . . ?
N8 P1 N3 P3 135.8(2) . . . . ?
N1 P1 N7 C13 102.1(3) . . . . ?
N1 P1 N7 C14 -48.3(4) . . . . ?
N3 P1 N7 C13 -131.3(3) . . . . ?
N3 P1 N7 C14 78.4(4) . . . . ?
N8 P1 N7 C13 -14.8(3) . . . . ?
N8 P1 N7 C14 -165.2(4) . . . . ?
N1 P1 N8 C7 65.5(3) . . . . ?
N1 P1 N8 C12 -114.5(2) . . . . ?
N3 P1 N8 C7 -61.5(3) . . . . ?
N3 P1 N8 C12 118.5(3) . . . . ?
N7 P1 N8 C7 -177.8(3) . . . . ?
N7 P1 N8 C12 2.2(3) . . . . ?
Cl3 P2 N1 P1 111.4(2) . . . . ?
Cl4 P2 N1 P1 -139.94(19) . . . . ?
N2 P2 N1 P1 -13.8(3) . . . . ?
Cl3 P2 N2 P3 -121.1(2) . . . . ?
Cl4 P2 N2 P3 131.75(19) . . . . ?
N1 P2 N2 P3 5.4(3) . . . . ?
Cl1 P3 N2 P2 133.80(19) . . . . ?
Cl2 P3 N2 P2 -118.2(2) . . . . ?
N3 P3 N2 P2 9.0(3) . . . . ?
Cl1 P3 N3 P1 -140.5(2) . . . . ?
Cl2 P3 N3 P1 109.8(2) . . . . ?
N2 P3 N3 P1 -16.6(3) . . . . ?
N6 P4 N4 P5 3.6(3) . . . . ?
N9 P4 N4 P5 129.5(3) . . . . ?
N10 P4 N4 P5 -124.4(3) . . . . ?
N4 P4 N6 P6 -8.5(3) . . . . ?
N9 P4 N6 P6 -135.1(3) . . . . ?
N10 P4 N6 P6 118.6(3) . . . . ?
N4 P4 N9 C8 -52.5(3) . . . . ?
N4 P4 N9 C9 113.3(3) . . . . ?
N6 P4 N9 C8 73.5(3) . . . . ?
N6 P4 N9 C9 -120.7(3) . . . . ?
N10 P4 N9 C8 -168.8(3) . . . . ?
N10 P4 N9 C9 -3.0(3) . . . . ?
N4 P4 N10 C10 -131.8(3) . . . . ?
N4 P4 N10 C11 83.1(4) . . . . ?
N6 P4 N10 C10 101.1(3) . . . . ?
N6 P4 N10 C11 -43.9(4) . . . . ?
N9 P4 N10 C10 -14.9(3) . . . . ?
N9 P4 N10 C11 -159.9(3) . . . . ?
Cl7 P5 N4 P4 127.3(2) . . . . ?
Cl8 P5 N4 P4 -124.0(2) . . . . ?
N5 P5 N4 P4 2.4(4) . . . . ?
Cl7 P5 N5 P6 -129.6(2) . . . . ?
Cl8 P5 N5 P6 123.3(2) . . . . ?
N4 P5 N5 P6 -4.3(4) . . . . ?
Cl5 P6 N5 P5 -126.3(2) . . . . ?
Cl6 P6 N5 P5 126.9(2) . . . . ?
N6 P6 N5 P5 -0.2(3) . . . . ?
Cl5 P6 N6 P4 132.4(2) . . . . ?
Cl6 P6 N6 P4 -118.8(2) . . . . ?
N5 P6 N6 P4 7.1(4) . . . . ?
P1 N7 C13 C12 22.5(4) . . . . ?
C14 N7 C13 C12 173.4(4) . . . . ?
P1 N8 C7 C3 -100.0(3) . . . . ?
C12 N8 C7 C3 80.0(4) . . . . ?
P1 N8 C12 C13 10.2(4) . . . . ?
C7 N8 C12 C13 -169.8(3) . . . . ?
P4 N9 C8 C5 -120.9(3) . . . . ?
C9 N9 C8 C5 74.4(5) . . . . ?
P4 N9 C9 C10 19.1(4) . . . . ?
C8 N9 C9 C10 -174.5(3) . . . . ?
P4 N10 C10 C9 27.5(4) . . . . ?
C11 N10 C10 C9 174.6(4) . . . . ?
C6 C1 C2 C3 -0.1(7) . . . . ?
C2 C1 C6 C5 -0.5(7) . . . . ?
C4 C3 C2 C1 0.0(6) . . . . ?
C7 C3 C2 C1 179.5(4) . . . . ?
C2 C3 C7 N8 -176.3(3) . . . . ?
C4 C3 C7 N8 3.2(5) . . . . ?
C5 C4 C3 C2 0.6(5) . . . . ?
C5 C4 C3 C7 -178.9(3) . . . . ?
C6 C5 C4 C3 -1.2(5) . . . . ?
C8 C5 C4 C3 176.7(3) . . . . ?
C4 C5 C6 C1 1.1(6) . . . . ?
C8 C5 C6 C1 -176.8(4) . . . . ?
C4 C5 C8 N9 23.9(5) . . . . ?
C6 C5 C8 N9 -158.3(4) . . . . ?
N9 C9 C10 N10 -28.3(4) . . . . ?
N8 C12 C13 N7 -19.8(4) . . . . ?

_refine_diff_density_max         0.625
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.066

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1485238'
_audit_update_record             
;
2016-06-13 deposited with the CCDC.
2016-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H26 Cl8 N10 P6'
_chemical_formula_sum            'C16 H26 Cl8 N10 P6'
_chemical_formula_weight         827.89

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   12.5574(6)
_cell_length_b                   17.0478(8)
_cell_length_c                   16.6323(8)
_cell_angle_alpha                90
_cell_angle_beta                 108.227(2)
_cell_angle_gamma                90
_cell_volume                     3381.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    99(2)
_cell_measurement_reflns_used    9939
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      26.01

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_F_000             1672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.979
_shelx_estimated_absorpt_T_min   0.758
_shelx_estimated_absorpt_T_max   0.851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.754
_exptl_absorpt_correction_T_max  0.847
_exptl_absorpt_process_details   'SADABS; Bruker, 2005'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      99(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24156
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.757
_diffrn_reflns_theta_max         26.052
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6607
_reflns_number_gt                4891
_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-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Ortep-3 for Windows (Farrugia, 1997)'

_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)+(0.0138P)²+20.0935P] 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         6607
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1259
_refine_ls_wR_factor_gt          0.1050
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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
Cl1 Cl 1.05229(11) 0.10838(9) 0.51940(8) 0.0411(3) Uani 1 1 d . . . . .
Cl2 Cl 0.86090(10) 0.20237(8) 0.55239(7) 0.0338(3) Uani 1 1 d . . . . .
Cl3 Cl 1.11153(11) 0.34385(10) 0.35187(10) 0.0508(4) Uani 1 1 d . . . . .
Cl4 Cl 0.93838(15) 0.43013(9) 0.41515(10) 0.0534(4) Uani 1 1 d . . . . .
Cl5 Cl 0.58979(10) 0.49399(8) -0.15478(8) 0.0349(3) Uani 1 1 d . . . . .
Cl6 Cl 0.71201(11) 0.62287(7) -0.22182(7) 0.0327(3) Uani 1 1 d . . . . .
Cl7 Cl 0.67208(11) 0.30314(8) -0.34621(9) 0.0410(3) Uani 1 1 d . . . . .
Cl8 Cl 0.79443(13) 0.42893(9) -0.41718(8) 0.0466(4) Uani 1 1 d . . . . .
P1 P 0.80696(10) 0.21370(8) 0.29812(7) 0.0261(3) Uani 1 1 d . . . . .
P2 P 0.97357(11) 0.32179(8) 0.38309(8) 0.0309(3) Uani 1 1 d . . . . .
P3 P 0.94163(10) 0.19160(8) 0.46556(7) 0.0257(3) Uani 1 1 d . . . . .
P4 P 0.91538(10) 0.42001(7) -0.14748(7) 0.0250(3) Uani 1 1 d . . . . .
P5 P 0.76235(10) 0.40121(7) -0.31035(7) 0.0251(3) Uani 1 1 d . . . . .
P6 P 0.71594(10) 0.50668(7) -0.20366(7) 0.0240(3) Uani 1 1 d . . . . .
N1 N 0.8777(3) 0.2943(2) 0.3041(2) 0.0304(9) Uani 1 1 d . . . . .
N2 N 1.0089(3) 0.2703(3) 0.4662(2) 0.0346(10) Uani 1 1 d . . . . .
N3 N 0.8592(3) 0.1600(2) 0.3809(2) 0.0278(9) Uani 1 1 d . . . . .
N4 N 0.8744(3) 0.3809(2) -0.2404(2) 0.0271(9) Uani 1 1 d . . . . .
N5 N 0.6807(3) 0.4659(2) -0.2936(2) 0.0304(9) Uani 1 1 d . . . . .
N6 N 0.8280(3) 0.4842(2) -0.1353(2) 0.0287(9) Uani 1 1 d . . . . .
N7 N 0.6719(3) 0.2260(3) 0.2796(3) 0.0333(10) Uani 1 1 d . . . . .
N8 N 0.7943(3) 0.1691(3) 0.2092(2) 0.0306(9) Uani 1 1 d . . . . .
N9 N 0.9436(3) 0.3525(2) -0.0736(2) 0.0279(9) Uani 1 1 d . . . . .
N10 N 1.0429(3) 0.4562(2) -0.1227(2) 0.0290(9) Uani 1 1 d . . . . .
C1 C 0.9158(4) 0.1052(3) -0.0283(3) 0.0366(12) Uani 1 1 d . . . . .
H1 H 0.9301 0.0647 -0.0629 0.044 Uiso 1 1 calc R U . . .
C2 C 0.9088(4) 0.0876(3) 0.0513(3) 0.0342(12) Uani 1 1 d . . . . .
H2 H 0.9189 0.0350 0.0712 0.041 Uiso 1 1 calc R U . . .
C3 C 0.8874(4) 0.1457(3) 0.1017(3) 0.0284(10) Uani 1 1 d . . . . .
C4 C 0.8708(4) 0.2222(3) 0.0709(3) 0.0295(11) Uani 1 1 d . . . . .
H4 H 0.8548 0.2626 0.1048 0.035 Uiso 1 1 calc R U . . .
C5 C 0.8773(4) 0.2401(3) -0.0086(3) 0.0308(11) Uani 1 1 d . . . . .
C6 C 0.9018(4) 0.1813(3) -0.0570(3) 0.0336(12) Uani 1 1 d . . . . .
H6 H 0.9092 0.1936 -0.1108 0.040 Uiso 1 1 calc R U . . .
C7 C 0.8847(4) 0.1273(3) 0.1895(3) 0.0338(12) Uani 1 1 d . . . . .
H7A H 0.8743 0.0701 0.1945 0.041 Uiso 1 1 calc R U . . .
H7B H 0.9573 0.1420 0.2311 0.041 Uiso 1 1 calc R U . . .
C8 C 0.8543(4) 0.3222(3) -0.0431(3) 0.0366(12) Uani 1 1 d . . . . .
H8A H 0.8454 0.3573 0.0018 0.044 Uiso 1 1 calc R U . . .
H8B H 0.7828 0.3226 -0.0903 0.044 Uiso 1 1 calc R U . . .
C9 C 1.0523(4) 0.3694(3) -0.0095(3) 0.0313(11) Uani 1 1 d . . . . .
H9A H 1.0887 0.3203 0.0172 0.038 Uiso 1 1 calc R U . . .
H9B H 1.0423 0.4045 0.0350 0.038 Uiso 1 1 calc R U . . .
C10 C 1.1219(4) 0.4090(3) -0.0574(3) 0.0318(11) Uani 1 1 d . . . . .
H10A H 1.1589 0.3695 -0.0833 0.038 Uiso 1 1 calc R U . . .
H10B H 1.1801 0.4427 -0.0191 0.038 Uiso 1 1 calc R U . . .
C11 C 1.0811(5) 0.4938(4) -0.1881(3) 0.0431(14) Uani 1 1 d . . . . .
H11A H 1.0914 0.4527 -0.2272 0.052 Uiso 1 1 calc R U . . .
H11B H 1.0215 0.5297 -0.2213 0.052 Uiso 1 1 calc R U . . .
C12 C 1.1862(6) 0.5384(4) -0.1558(4) 0.0588(18) Uani 1 1 d . . . . .
H12A H 1.2473 0.5028 -0.1267 0.088 Uiso 1 1 calc R U . . .
H12B H 1.1778 0.5786 -0.1161 0.088 Uiso 1 1 calc R U . . .
H12C H 1.2036 0.5636 -0.2032 0.088 Uiso 1 1 calc R U . . .
C13 C 0.6783(4) 0.1491(3) 0.1615(3) 0.0379(13) Uani 1 1 d . . . . .
H13A H 0.6654 0.1534 0.0999 0.045 Uiso 1 1 calc R U . . .
H13B H 0.6600 0.0951 0.1748 0.045 Uiso 1 1 calc R U . . .
C14 C 0.6087(4) 0.2087(4) 0.1904(3) 0.0416(14) Uani 1 1 d . . . . .
H14A H 0.5986 0.2568 0.1556 0.050 Uiso 1 1 calc R U . . .
H14B H 0.5339 0.1869 0.1858 0.050 Uiso 1 1 calc R U . . .
C15 C 0.6257(5) 0.2779(3) 0.3294(4) 0.0427(13) Uani 1 1 d . . . . .
H15A H 0.5527 0.2565 0.3302 0.051 Uiso 1 1 calc R U . . .
H15B H 0.6766 0.2782 0.3885 0.051 Uiso 1 1 calc R U . . .
C16 C 0.6084(5) 0.3614(4) 0.2976(4) 0.0541(17) Uani 1 1 d . . . . .
H16A H 0.5529 0.3624 0.2410 0.081 Uiso 1 1 calc R U . . .
H16B H 0.6797 0.3827 0.2947 0.081 Uiso 1 1 calc R U . . .
H16C H 0.5816 0.3933 0.3363 0.081 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
Cl1 P3 1.9918(18) . ?
Cl2 P3 2.0156(16) . ?
Cl3 P2 1.9937(18) . ?
Cl4 P2 2.010(2) . ?
Cl5 P6 2.0056(17) . ?
Cl6 P6 2.0021(17) . ?
Cl7 P5 2.0032(18) . ?
Cl8 P5 1.9977(17) . ?
P1 N1 1.622(4) . ?
P1 N3 1.612(4) . ?
P1 N7 1.640(4) . ?
P1 N8 1.626(4) . ?
P2 N1 1.551(4) . ?
P2 N2 1.579(4) . ?
P3 N2 1.583(4) . ?
P3 N3 1.560(4) . ?
P4 N4 1.613(4) . ?
P4 N6 1.607(4) . ?
P4 N9 1.639(4) . ?
P4 N10 1.643(4) . ?
P5 N4 1.558(4) . ?
P5 N5 1.588(4) . ?
P6 N5 1.582(4) . ?
P6 N6 1.555(4) . ?
N7 C14 1.476(6) . ?
N7 C15 1.452(7) . ?
N8 C7 1.462(6) . ?
N8 C13 1.465(6) . ?
N9 C8 1.462(6) . ?
N9 C9 1.473(6) . ?
N10 C10 1.461(6) . ?
N10 C11 1.467(6) . ?
C1 C2 1.387(7) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C2 1.378(7) . ?
C3 C7 1.504(6) . ?
C4 C3 1.394(7) . ?
C4 H4 0.9500 . ?
C5 C4 1.383(7) . ?
C5 C6 1.380(7) . ?
C6 C1 1.376(7) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C5 1.506(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C9 1.513(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C11 1.473(8) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.512(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.511(8) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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 P1 N7 114.7(2) . . ?
N1 P1 N8 110.4(2) . . ?
N3 P1 N1 111.1(2) . . ?
N3 P1 N7 110.7(2) . . ?
N3 P1 N8 114.1(2) . . ?
N8 P1 N7 95.0(2) . . ?
Cl3 P2 Cl4 100.18(9) . . ?
N1 P2 Cl3 110.12(17) . . ?
N1 P2 Cl4 109.01(18) . . ?
N1 P2 N2 120.3(2) . . ?
N2 P2 Cl3 107.66(17) . . ?
N2 P2 Cl4 107.70(18) . . ?
Cl1 P3 Cl2 100.33(7) . . ?
N2 P3 Cl1 107.72(17) . . ?
N2 P3 Cl2 107.79(17) . . ?
N3 P3 Cl1 109.43(17) . . ?
N3 P3 Cl2 109.75(16) . . ?
N3 P3 N2 120.0(2) . . ?
N4 P4 N9 111.0(2) . . ?
N4 P4 N10 112.9(2) . . ?
N6 P4 N4 112.1(2) . . ?
N6 P4 N9 112.3(2) . . ?
N6 P4 N10 111.3(2) . . ?
N9 P4 N10 96.3(2) . . ?
Cl8 P5 Cl7 100.68(8) . . ?
N4 P5 Cl7 109.35(17) . . ?
N4 P5 Cl8 109.30(16) . . ?
N4 P5 N5 120.3(2) . . ?
N5 P5 Cl7 107.19(17) . . ?
N5 P5 Cl8 108.22(16) . . ?
Cl6 P6 Cl5 100.52(7) . . ?
N5 P6 Cl5 108.25(17) . . ?
N5 P6 Cl6 107.81(17) . . ?
N6 P6 Cl5 109.00(16) . . ?
N6 P6 Cl6 109.15(17) . . ?
N6 P6 N5 120.3(2) . . ?
P2 N1 P1 125.0(2) . . ?
P2 N2 P3 117.5(2) . . ?
P3 N3 P1 123.5(3) . . ?
P5 N4 P4 124.5(2) . . ?
P6 N5 P5 117.8(2) . . ?
P6 N6 P4 124.9(2) . . ?
C14 N7 P1 111.3(3) . . ?
C15 N7 P1 123.1(4) . . ?
C15 N7 C14 120.7(4) . . ?
C7 N8 P1 124.8(3) . . ?
C7 N8 C13 118.4(4) . . ?
C13 N8 P1 113.5(3) . . ?
C8 N9 P4 119.9(3) . . ?
C8 N9 C9 117.2(4) . . ?
C9 N9 P4 109.8(3) . . ?
C10 N10 P4 111.2(3) . . ?
C10 N10 C11 119.2(4) . . ?
C11 N10 P4 119.8(3) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 C2 119.7(5) . . ?
C6 C1 H1 120.1 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(5) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 C4 118.9(4) . . ?
C2 C3 C7 120.6(5) . . ?
C4 C3 C7 120.5(4) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.8(5) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C8 120.5(5) . . ?
C6 C5 C4 119.2(5) . . ?
C6 C5 C8 120.2(4) . . ?
C1 C6 C5 120.7(5) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
N8 C7 C3 111.8(4) . . ?
N8 C7 H7A 109.3 . . ?
N8 C7 H7B 109.3 . . ?
C3 C7 H7A 109.3 . . ?
C3 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
N9 C8 C5 112.6(4) . . ?
N9 C8 H8A 109.1 . . ?
N9 C8 H8B 109.1 . . ?
C5 C8 H8A 109.1 . . ?
C5 C8 H8B 109.1 . . ?
H8B C8 H8A 107.8 . . ?
N9 C9 C10 105.3(4) . . ?
N9 C9 H9A 110.7 . . ?
N9 C9 H9B 110.7 . . ?
C10 C9 H9A 110.7 . . ?
C10 C9 H9B 110.7 . . ?
H9A C9 H9B 108.8 . . ?
N10 C10 C9 105.5(4) . . ?
N10 C10 H10A 110.6 . . ?
N10 C10 H10B 110.6 . . ?
C9 C10 H10A 110.6 . . ?
C9 C10 H10B 110.6 . . ?
H10B C10 H10A 108.8 . . ?
N10 C11 C12 114.8(5) . . ?
N10 C11 H11A 108.6 . . ?
N10 C11 H11B 108.6 . . ?
C12 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
H11B C11 H11A 107.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12B C12 H12A 109.5 . . ?
H12B C12 H12C 109.5 . . ?
H12C C12 H12A 109.5 . . ?
N8 C13 C14 104.3(4) . . ?
N8 C13 H13A 110.9 . . ?
N8 C13 H13B 110.9 . . ?
C14 C13 H13A 110.9 . . ?
C14 C13 H13B 110.9 . . ?
H13B C13 H13A 108.9 . . ?
N7 C14 C13 105.7(4) . . ?
N7 C14 H14A 110.6 . . ?
N7 C14 H14B 110.6 . . ?
C13 C14 H14A 110.6 . . ?
C13 C14 H14B 110.6 . . ?
H14A C14 H14B 108.7 . . ?
N7 C15 C16 114.3(5) . . ?
N7 C15 H15A 108.7 . . ?
N7 C15 H15B 108.7 . . ?
C16 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
H15B C15 H15A 107.6 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16B C16 H16A 109.5 . . ?
H16B C16 H16C 109.5 . . ?
H16C C16 H16A 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
N3 P1 N1 P2 -7.2(4) . . . . ?
N7 P1 N1 P2 119.3(3) . . . . ?
N8 P1 N1 P2 -134.8(3) . . . . ?
N1 P1 N3 P3 17.2(4) . . . . ?
N7 P1 N3 P3 -111.5(3) . . . . ?
N8 P1 N3 P3 142.7(3) . . . . ?
N1 P1 N7 C14 103.1(4) . . . . ?
N1 P1 N7 C15 -52.0(5) . . . . ?
N3 P1 N7 C14 -130.2(4) . . . . ?
N3 P1 N7 C15 74.7(4) . . . . ?
N8 P1 N7 C14 -12.1(4) . . . . ?
N8 P1 N7 C15 -167.1(4) . . . . ?
N1 P1 N8 C7 73.3(4) . . . . ?
N1 P1 N8 C13 -127.6(4) . . . . ?
N3 P1 N8 C7 -52.6(5) . . . . ?
N3 P1 N8 C13 106.5(4) . . . . ?
N7 P1 N8 C7 -168.0(4) . . . . ?
N7 P1 N8 C13 -8.9(4) . . . . ?
Cl3 P2 N1 P1 125.8(3) . . . . ?
Cl4 P2 N1 P1 -125.2(3) . . . . ?
N2 P2 N1 P1 -0.2(4) . . . . ?
Cl3 P2 N2 P3 -128.3(3) . . . . ?
Cl4 P2 N2 P3 124.5(3) . . . . ?
N1 P2 N2 P3 -1.1(4) . . . . ?
Cl1 P3 N2 P2 136.7(3) . . . . ?
Cl2 P3 N2 P2 -115.8(3) . . . . ?
N3 P3 N2 P2 10.7(4) . . . . ?
Cl1 P3 N3 P1 -145.1(2) . . . . ?
Cl2 P3 N3 P1 105.7(3) . . . . ?
N2 P3 N3 P1 -19.9(4) . . . . ?
N6 P4 N4 P5 -1.0(4) . . . . ?
N9 P4 N4 P5 125.4(3) . . . . ?
N10 P4 N4 P5 -127.7(3) . . . . ?
N4 P4 N6 P6 0.5(4) . . . . ?
N9 P4 N6 P6 -125.3(3) . . . . ?
N10 P4 N6 P6 128.0(3) . . . . ?
N4 P4 N9 C8 -87.0(4) . . . . ?
N4 P4 N9 C9 132.9(3) . . . . ?
N6 P4 N9 C8 39.4(4) . . . . ?
N6 P4 N9 C9 -100.8(3) . . . . ?
N10 P4 N9 C8 155.5(4) . . . . ?
N10 P4 N9 C9 15.4(3) . . . . ?
N4 P4 N10 C10 -109.2(3) . . . . ?
N4 P4 N10 C11 36.4(5) . . . . ?
N6 P4 N10 C10 123.6(3) . . . . ?
N6 P4 N10 C11 -90.8(4) . . . . ?
N9 P4 N10 C10 6.7(4) . . . . ?
N9 P4 N10 C11 152.3(4) . . . . ?
Cl7 P5 N4 P4 -123.1(3) . . . . ?
Cl8 P5 N4 P4 127.6(3) . . . . ?
N5 P5 N4 P4 1.5(4) . . . . ?
Cl7 P5 N5 P6 124.2(2) . . . . ?
Cl8 P5 N5 P6 -127.9(2) . . . . ?
N4 P5 N5 P6 -1.4(4) . . . . ?
Cl5 P6 N5 P5 -125.3(2) . . . . ?
Cl6 P6 N5 P5 126.8(2) . . . . ?
N6 P6 N5 P5 0.9(4) . . . . ?
Cl5 P6 N6 P4 125.4(3) . . . . ?
Cl6 P6 N6 P4 -125.7(3) . . . . ?
N5 P6 N6 P4 -0.4(4) . . . . ?
P1 N7 C14 C13 28.2(5) . . . . ?
C15 N7 C14 C13 -176.1(4) . . . . ?
P1 N7 C15 C16 89.1(6) . . . . ?
C14 N7 C15 C16 -63.7(7) . . . . ?
P1 N8 C7 C3 -135.9(4) . . . . ?
C13 N8 C7 C3 65.9(6) . . . . ?
P1 N8 C13 C14 25.8(5) . . . . ?
C7 N8 C13 C14 -173.7(4) . . . . ?
P4 N9 C8 C5 153.6(4) . . . . ?
C9 N9 C8 C5 -69.0(6) . . . . ?
P4 N9 C9 C10 -31.6(5) . . . . ?
C8 N9 C9 C10 -173.0(4) . . . . ?
P4 N10 C10 C9 -25.7(5) . . . . ?
C11 N10 C10 C9 -171.5(4) . . . . ?
P4 N10 C11 C12 167.6(5) . . . . ?
C10 N10 C11 C12 -49.6(7) . . . . ?
C6 C1 C2 C3 0.4(8) . . . . ?
C4 C3 C2 C1 1.2(7) . . . . ?
C7 C3 C2 C1 -177.4(5) . . . . ?
C2 C3 C7 N8 -139.9(5) . . . . ?
C4 C3 C7 N8 41.6(6) . . . . ?
C5 C4 C3 C2 -1.0(7) . . . . ?
C5 C4 C3 C7 177.6(4) . . . . ?
C6 C5 C4 C3 -0.7(7) . . . . ?
C8 C5 C4 C3 177.3(4) . . . . ?
C4 C5 C6 C1 2.3(7) . . . . ?
C8 C5 C6 C1 -175.7(5) . . . . ?
C5 C6 C1 C2 -2.1(8) . . . . ?
N9 C8 C5 C4 128.5(5) . . . . ?
N9 C8 C5 C6 -53.5(6) . . . . ?
N10 C10 C9 N9 35.1(5) . . . . ?
N8 C13 C14 N7 -32.2(5) . . . . ?

_refine_diff_density_max         0.631
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.114

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1485240'
_audit_update_record             
;
2016-06-13 deposited with the CCDC.
2016-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H42 N8 O P3'
_chemical_formula_sum            'C23 H42 N8 O P3'
_chemical_formula_weight         539.55

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   38.868(2)
_cell_length_b                   9.1882(6)
_cell_length_c                   16.6047(10)
_cell_angle_alpha                90
_cell_angle_beta                 104.465(3)
_cell_angle_gamma                90
_cell_volume                     5742.0(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_F_000             2312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.238
_shelx_estimated_absorpt_T_min   0.890
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_process_details   'SADABS; Bruker, 2005'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11717
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       54
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.722
_diffrn_reflns_theta_max         30.606
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.842
_diffrn_measured_fraction_theta_full 0.908
_diffrn_reflns_Laue_measured_fraction_max 0.842
_diffrn_reflns_Laue_measured_fraction_full 0.908
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_point_group_measured_fraction_full 0.908
_reflns_number_total             7452
_reflns_number_gt                4581
_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    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Ortep-3 for Windows (Farrugia, 1997)'

_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)+(0.1021P)²+2.7731P] 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         7452
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0608
_refine_ls_wR_factor_ref         0.1955
_refine_ls_wR_factor_gt          0.1683
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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_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 0.12881(2) 0.67820(7) 0.22904(4) 0.04210(18) Uani 1 1 d . . . . .
P2 P 0.14720(2) 0.43030(7) 0.15180(4) 0.04340(19) Uani 1 1 d . . . . .
P3 P 0.12251(2) 0.67798(8) 0.05819(4) 0.0467(2) Uani 1 1 d . . . . .
O1 O 0.15833(5) 0.7743(2) 0.28963(11) 0.0520(5) Uani 1 1 d . . . . .
N1 N 0.14166(6) 0.5139(2) 0.23160(13) 0.0486(5) Uani 1 1 d . . . . .
N2 N 0.13133(6) 0.5087(2) 0.06448(13) 0.0480(5) Uani 1 1 d . . . . .
N3 N 0.11883(6) 0.7561(2) 0.14169(14) 0.0522(6) Uani 1 1 d . . . . .
N4 N 0.09537(5) 0.6956(2) 0.27394(14) 0.0481(5) Uani 1 1 d . . . . .
N5 N 0.13006(6) 0.2645(3) 0.14119(14) 0.0539(6) Uani 1 1 d . . . . .
N6 N 0.19000(6) 0.3943(3) 0.17106(16) 0.0591(6) Uani 1 1 d . . . . .
N7 N 0.08626(7) 0.6964(3) -0.01856(16) 0.0648(7) Uani 1 1 d . . . . .
N8 N 0.15132(7) 0.7752(3) 0.02364(15) 0.0599(6) Uani 1 1 d . . . . .
C1 C 0.0000 0.9283(5) 0.2500 0.108(2) Uani 1 2 d S T P . .
H1 H 0.0000 1.0295 0.2500 0.130 Uiso 1 2 calc R U P . .
C2 C 0.02963(8) 0.8547(4) 0.2421(3) 0.0814(11) Uani 1 1 d . . . . .
H2 H 0.0496 0.9061 0.2370 0.098 Uiso 1 1 calc R U . . .
C3 C 0.02992(7) 0.7050(3) 0.24188(17) 0.0490(6) Uani 1 1 d . . . . .
C4 C 0.0000 0.6319(4) 0.2500 0.0465(8) Uani 1 2 d S T P . .
H4 H 0.0000 0.5307 0.2500 0.056 Uiso 1 2 calc R U P . .
C5 C 0.06225(7) 0.6240(4) 0.2309(2) 0.0616(8) Uani 1 1 d . . . . .
H5A H 0.0620 0.5258 0.2522 0.074 Uiso 1 1 calc R U . . .
H5B H 0.0613 0.6173 0.1720 0.074 Uiso 1 1 calc R U . . .
C6 C 0.10302(8) 0.6762(3) 0.36453(18) 0.0582(7) Uani 1 1 d . . . . .
H6A H 0.1089 0.5752 0.3783 0.070 Uiso 1 1 calc R U . . .
H6B H 0.0820 0.7003 0.3835 0.070 Uiso 1 1 calc R U . . .
C7 C 0.13349(9) 0.7717(4) 0.40849(18) 0.0624(8) Uani 1 1 d . . . . .
H7A H 0.1267 0.8731 0.3992 0.075 Uiso 1 1 calc R U . . .
H7B H 0.1388 0.7533 0.4678 0.075 Uiso 1 1 calc R U . . .
C8 C 0.16571(8) 0.7431(4) 0.37782(18) 0.0598(7) Uani 1 1 d . . . . .
H8A H 0.1851 0.8038 0.4078 0.072 Uiso 1 1 calc R U . . .
H8B H 0.1728 0.6421 0.3877 0.072 Uiso 1 1 calc R U . . .
C9 C 0.09161(9) 0.2483(4) 0.1029(2) 0.0773(10) Uani 1 1 d . . . . .
H9A H 0.0877 0.2116 0.0465 0.093 Uiso 1 1 calc R U . . .
H9B H 0.0797 0.3414 0.1011 0.093 Uiso 1 1 calc R U . . .
C10 C 0.07808(12) 0.1453(6) 0.1545(3) 0.1137(17) Uani 1 1 d . . . . .
H10A H 0.0733 0.0520 0.1267 0.136 Uiso 1 1 calc R U . . .
H10B H 0.0562 0.1814 0.1651 0.136 Uiso 1 1 calc R U . . .
C11 C 0.10533(11) 0.1299(5) 0.2328(3) 0.0955(13) Uani 1 1 d . . . . .
H11A H 0.1058 0.0311 0.2536 0.115 Uiso 1 1 calc R U . . .
H11B H 0.1007 0.1958 0.2745 0.115 Uiso 1 1 calc R U . . .
C12 C 0.13931(9) 0.1661(3) 0.2136(2) 0.0663(8) Uani 1 1 d . . . . .
H12A H 0.1508 0.0788 0.2002 0.080 Uiso 1 1 calc R U . . .
H12B H 0.1552 0.2140 0.2605 0.080 Uiso 1 1 calc R U . . .
C13 C 0.20483(10) 0.3133(5) 0.1120(3) 0.0987(14) Uani 1 1 d . . . . .
H13A H 0.2012 0.2096 0.1171 0.118 Uiso 1 1 calc R U . . .
H13B H 0.1937 0.3429 0.0554 0.118 Uiso 1 1 calc R U . . .
C14 C 0.24259(13) 0.3477(9) 0.1333(5) 0.164(3) Uani 1 1 d . . . . .
H14A H 0.2564 0.2590 0.1460 0.197 Uiso 1 1 calc R U . . .
H14B H 0.2488 0.3948 0.0866 0.197 Uiso 1 1 calc R U . . .
C15 C 0.25025(11) 0.4409(8) 0.2029(5) 0.157(3) Uani 1 1 d . . . . .
H15A H 0.2620 0.5280 0.1902 0.188 Uiso 1 1 calc R U . . .
H15B H 0.2661 0.3924 0.2496 0.188 Uiso 1 1 calc R U . . .
C16 C 0.21730(9) 0.4805(5) 0.2247(3) 0.0987(14) Uani 1 1 d . . . . .
H16A H 0.2189 0.4584 0.2827 0.118 Uiso 1 1 calc R U . . .
H16B H 0.2124 0.5834 0.2155 0.118 Uiso 1 1 calc R U . . .
C17 C 0.07287(12) 0.8450(5) -0.0432(3) 0.0951(13) Uani 1 1 d . . . . .
H17A H 0.0847 0.9162 -0.0025 0.114 Uiso 1 1 calc R U . . .
H17B H 0.0766 0.8707 -0.0970 0.114 Uiso 1 1 calc R U . . .
C18 C 0.03495(17) 0.8384(9) -0.0468(8) 0.230(5) Uani 1 1 d . . . . .
H18A H 0.0305 0.8798 0.0035 0.276 Uiso 1 1 calc R U . . .
H18B H 0.0216 0.8939 -0.0940 0.276 Uiso 1 1 calc R U . . .
C19 C 0.02396(14) 0.6890(7) -0.0547(6) 0.171(3) Uani 1 1 d . . . . .
H19A H 0.0129 0.6663 -0.1124 0.205 Uiso 1 1 calc R U . . .
H19B H 0.0069 0.6707 -0.0221 0.205 Uiso 1 1 calc R U . . .
C20 C 0.05574(8) 0.5987(4) -0.0244(2) 0.0784(10) Uani 1 1 d . . . . .
H20A H 0.0563 0.5197 -0.0628 0.094 Uiso 1 1 calc R U . . .
H20B H 0.0561 0.5579 0.0297 0.094 Uiso 1 1 calc R U . . .
C21 C 0.16273(13) 0.7274(5) -0.0504(2) 0.0937(13) Uani 1 1 d . . . . .
H21A H 0.1687 0.6247 -0.0466 0.112 Uiso 1 1 calc R U . . .
H21B H 0.1440 0.7438 -0.1005 0.112 Uiso 1 1 calc R U . . .
C22 C 0.19364(14) 0.8144(7) -0.0511(4) 0.130(2) Uani 1 1 d . . . . .
H22A H 0.1877 0.8866 -0.0951 0.156 Uiso 1 1 calc R U . . .
H22B H 0.2123 0.7529 -0.0616 0.156 Uiso 1 1 calc R U . . .
C23 C 0.20580(11) 0.8860(6) 0.0288(3) 0.1030(14) Uani 1 1 d . . . . .
H23A H 0.2091 0.9893 0.0212 0.124 Uiso 1 1 calc R U . . .
H23B H 0.2283 0.8449 0.0594 0.124 Uiso 1 1 calc R U . . .
C24 C 0.17847(12) 0.8627(5) 0.0742(3) 0.0952(14) Uani 1 1 d . . . . .
H24A H 0.1886 0.8141 0.1266 0.114 Uiso 1 1 calc R U . . .
H24B H 0.1687 0.9553 0.0858 0.114 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 O1 1.5913(18) . ?
P1 N1 1.587(2) . ?
P1 N3 1.576(2) . ?
P1 N4 1.660(2) . ?
P2 N1 1.592(2) . ?
P2 N2 1.598(2) . ?
P2 N5 1.654(2) . ?
P2 N6 1.647(2) . ?
P3 N2 1.590(2) . ?
P3 N3 1.599(2) . ?
P3 N7 1.656(2) . ?
P3 N8 1.644(3) . ?
O1 C8 1.449(3) . ?
N4 C5 1.464(3) . ?
N4 C6 1.469(4) . ?
N5 C9 1.478(4) . ?
N5 C12 1.475(4) . ?
N6 C13 1.459(4) . ?
N6 C16 1.440(4) . ?
N7 C17 1.482(5) . ?
N7 C20 1.472(4) . ?
N8 C21 1.474(5) . ?
N8 C24 1.422(4) . ?
C1 C2 1.369(4) 2 ?
C1 H1 0.9300 . ?
C2 C1 1.369(4) . ?
C2 H2 0.9300 . ?
C3 C2 1.376(4) . ?
C3 C5 1.511(4) . ?
C4 C3 1.378(3) . ?
C4 C3 1.378(3) 2 ?
C4 H4 0.9300 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.508(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C7 1.488(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.460(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C10 1.464(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C11 1.472(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.456(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C14 1.410(8) . ?
C15 C16 1.461(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.462(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C18 1.434(9) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C19 1.469(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C21 1.446(6) . ?
C22 C23 1.451(6) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.463(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?

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
O1 P1 N4 100.62(11) . . ?
N1 P1 O1 109.79(11) . . ?
N1 P1 N4 110.87(12) . . ?
N3 P1 O1 107.61(12) . . ?
N3 P1 N1 117.37(12) . . ?
N3 P1 N4 109.23(12) . . ?
N1 P2 N2 115.82(12) . . ?
N1 P2 N5 113.47(13) . . ?
N1 P2 N6 105.98(12) . . ?
N2 P2 N5 105.34(12) . . ?
N2 P2 N6 114.13(13) . . ?
N6 P2 N5 101.32(13) . . ?
N2 P3 N3 116.52(12) . . ?
N2 P3 N7 106.19(13) . . ?
N2 P3 N8 113.58(14) . . ?
N3 P3 N7 112.22(14) . . ?
N3 P3 N8 105.96(13) . . ?
N8 P3 N7 101.45(14) . . ?
C8 O1 P1 117.30(17) . . ?
P1 N1 P2 122.94(14) . . ?
P3 N2 P2 121.90(14) . . ?
P1 N3 P3 122.63(15) . . ?
C5 N4 P1 115.40(18) . . ?
C5 N4 C6 112.0(2) . . ?
C6 N4 P1 117.87(18) . . ?
C9 N5 P2 118.4(2) . . ?
C12 N5 P2 117.91(19) . . ?
C12 N5 C9 107.7(2) . . ?
C13 N6 P2 121.4(2) . . ?
C16 N6 P2 124.2(2) . . ?
C16 N6 C13 110.0(3) . . ?
C17 N7 P3 118.7(2) . . ?
C20 N7 P3 120.3(2) . . ?
C20 N7 C17 108.8(3) . . ?
C21 N8 P3 120.1(2) . . ?
C24 N8 P3 124.9(2) . . ?
C24 N8 C21 109.1(3) . . ?
C2 C1 C2 120.8(5) 2 . ?
C2 C1 H1 119.6 2 . ?
C2 C1 H1 119.6 . . ?
C1 C2 C3 120.1(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 118.6(3) . . ?
C2 C3 C5 120.1(3) . . ?
C4 C3 C5 121.3(3) . . ?
C3 C4 C3 121.7(4) 2 . ?
C3 C4 H4 119.2 2 . ?
C3 C4 H4 119.2 . . ?
N4 C5 C3 112.1(2) . . ?
N4 C5 H5A 109.2 . . ?
N4 C5 H5B 109.2 . . ?
C3 C5 H5A 109.2 . . ?
C3 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
N4 C6 C7 111.0(2) . . ?
N4 C6 H6A 109.4 . . ?
N4 C6 H6B 109.4 . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C8 C7 C6 111.0(3) . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
O1 C8 C7 109.9(2) . . ?
O1 C8 H8A 109.7 . . ?
O1 C8 H8B 109.7 . . ?
C7 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
N5 C9 H9A 110.4 . . ?
N5 C9 H9B 110.4 . . ?
C10 C9 N5 106.6(3) . . ?
C10 C9 H9A 110.4 . . ?
C10 C9 H9B 110.4 . . ?
H9B C9 H9A 108.6 . . ?
C9 C10 C11 107.3(3) . . ?
C9 C10 H10A 110.3 . . ?
C9 C10 H10B 110.3 . . ?
C11 C10 H10A 110.3 . . ?
C11 C10 H10B 110.3 . . ?
H10A C10 H10B 108.5 . . ?
C10 C11 C12 106.0(3) . . ?
C10 C11 H11A 110.5 . . ?
C10 C11 H11B 110.5 . . ?
C12 C11 H11A 110.5 . . ?
C12 C11 H11B 110.5 . . ?
H11A C11 H11B 108.7 . . ?
C11 C12 N5 105.4(3) . . ?
C11 C12 H12A 110.7 . . ?
C11 C12 H12B 110.7 . . ?
N5 C12 H12A 110.7 . . ?
N5 C12 H12B 110.7 . . ?
H12A C12 H12B 108.8 . . ?
C14 C13 N6 105.6(4) . . ?
C14 C13 H13A 110.6 . . ?
C14 C13 H13B 110.6 . . ?
N6 C13 H13A 110.6 . . ?
N6 C13 H13B 110.6 . . ?
H13A C13 H13B 108.7 . . ?
C13 C14 H14A 109.9 . . ?
C13 C14 H14B 109.9 . . ?
C15 C14 C13 109.0(4) . . ?
C15 C14 H14A 109.9 . . ?
C15 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
C14 C15 C16 109.6(4) . . ?
C14 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
C16 C15 H15A 109.7 . . ?
C16 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
N6 C16 C15 105.4(4) . . ?
N6 C16 H16A 110.7 . . ?
N6 C16 H16B 110.7 . . ?
C15 C16 H16A 110.7 . . ?
C15 C16 H16B 110.7 . . ?
H16A C16 H16B 108.8 . . ?
C18 C17 N7 104.7(4) . . ?
C18 C17 H17A 110.8 . . ?
C18 C17 H17B 110.8 . . ?
N7 C17 H17A 110.8 . . ?
N7 C17 H17B 110.8 . . ?
H17A C17 H17B 108.9 . . ?
C17 C18 H18A 110.0 . . ?
C17 C18 H18B 110.0 . . ?
C19 C18 C17 108.5(5) . . ?
C19 C18 H18A 110.0 . . ?
C19 C18 H18B 110.0 . . ?
H18A C18 H18B 108.4 . . ?
C18 C19 C20 107.7(4) . . ?
C18 C19 H19A 110.2 . . ?
C18 C19 H19B 110.2 . . ?
C20 C19 H19A 110.2 . . ?
C20 C19 H19B 110.2 . . ?
H19A C19 H19B 108.5 . . ?
C19 C20 N7 105.9(4) . . ?
C19 C20 H20A 110.6 . . ?
C19 C20 H20B 110.6 . . ?
N7 C20 H20A 110.6 . . ?
N7 C20 H20B 110.6 . . ?
H20A C20 H20B 108.7 . . ?
C22 C21 N8 105.4(3) . . ?
C22 C21 H21A 110.7 . . ?
C22 C21 H21B 110.7 . . ?
N8 C21 H21A 110.7 . . ?
N8 C21 H21B 110.7 . . ?
H21A C21 H21B 108.8 . . ?
C21 C22 C23 108.9(4) . . ?
C21 C22 H22A 109.9 . . ?
C21 C22 H22B 109.9 . . ?
C23 C22 H22A 109.9 . . ?
C23 C22 H22B 109.9 . . ?
H22A C22 H22B 108.3 . . ?
C22 C23 C24 107.0(3) . . ?
C22 C23 H23A 110.3 . . ?
C22 C23 H23B 110.3 . . ?
C24 C23 H23A 110.3 . . ?
C24 C23 H23B 110.3 . . ?
H23A C23 H23B 108.6 . . ?
N8 C24 C23 107.8(3) . . ?
N8 C24 H24A 110.1 . . ?
N8 C24 H24B 110.1 . . ?
C23 C24 H24A 110.1 . . ?
C23 C24 H24B 110.1 . . ?
H24A C24 H24B 108.5 . . ?

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
N1 P1 O1 C8 -65.1(2) . . . . ?
N3 P1 O1 C8 166.1(2) . . . . ?
N4 P1 O1 C8 51.8(2) . . . . ?
O1 P1 N1 P2 -119.09(16) . . . . ?
N3 P1 N1 P2 4.2(2) . . . . ?
N4 P1 N1 P2 130.63(16) . . . . ?
O1 P1 N3 P3 122.19(17) . . . . ?
N1 P1 N3 P3 -2.2(2) . . . . ?
N4 P1 N3 P3 -129.41(17) . . . . ?
O1 P1 N4 C5 177.3(2) . . . . ?
N1 P1 N4 C5 -66.6(2) . . . . ?
N3 P1 N4 C5 64.2(2) . . . . ?
O1 P1 N4 C6 -46.7(2) . . . . ?
N1 P1 N4 C6 69.4(2) . . . . ?
N3 P1 N4 C6 -159.8(2) . . . . ?
N2 P2 N1 P1 -12.6(2) . . . . ?
N5 P2 N1 P1 -134.60(16) . . . . ?
N6 P2 N1 P1 115.10(18) . . . . ?
N1 P2 N2 P3 19.8(2) . . . . ?
N5 P2 N2 P3 146.06(16) . . . . ?
N6 P2 N2 P3 -103.71(18) . . . . ?
N1 P2 N5 C9 81.8(3) . . . . ?
N2 P2 N5 C9 -45.9(3) . . . . ?
N6 P2 N5 C9 -165.0(3) . . . . ?
N1 P2 N5 C12 -50.8(3) . . . . ?
N2 P2 N5 C12 -178.5(2) . . . . ?
N6 P2 N5 C12 62.4(2) . . . . ?
N1 P2 N6 C13 178.0(3) . . . . ?
N2 P2 N6 C13 -53.4(3) . . . . ?
N5 P2 N6 C13 59.3(3) . . . . ?
N1 P2 N6 C16 -27.9(4) . . . . ?
N2 P2 N6 C16 100.8(3) . . . . ?
N5 P2 N6 C16 -146.5(3) . . . . ?
N3 P3 N2 P2 -18.1(2) . . . . ?
N7 P3 N2 P2 -143.87(17) . . . . ?
N8 P3 N2 P2 105.51(17) . . . . ?
N2 P3 N3 P1 8.9(2) . . . . ?
N7 P3 N3 P1 131.56(18) . . . . ?
N8 P3 N3 P1 -118.57(19) . . . . ?
N2 P3 N7 C17 -175.9(3) . . . . ?
N3 P3 N7 C17 55.8(3) . . . . ?
N8 P3 N7 C17 -56.9(3) . . . . ?
N2 P3 N7 C20 46.0(3) . . . . ?
N3 P3 N7 C20 -82.4(3) . . . . ?
N8 P3 N7 C20 164.9(3) . . . . ?
N2 P3 N8 C21 46.8(3) . . . . ?
N3 P3 N8 C21 176.0(3) . . . . ?
N7 P3 N8 C21 -66.7(3) . . . . ?
N2 P3 N8 C24 -103.0(4) . . . . ?
N3 P3 N8 C24 26.1(4) . . . . ?
N7 P3 N8 C24 143.5(4) . . . . ?
P1 O1 C8 C7 -63.2(3) . . . . ?
P1 N4 C5 C3 -147.9(2) . . . . ?
C6 N4 C5 C3 73.6(3) . . . . ?
P1 N4 C6 C7 52.5(3) . . . . ?
C5 N4 C6 C7 -170.1(2) . . . . ?
P2 N5 C9 C10 -134.7(3) . . . . ?
C12 N5 C9 C10 2.3(4) . . . . ?
P2 N5 C12 C11 119.5(3) . . . . ?
C9 N5 C12 C11 -17.7(4) . . . . ?
P2 N6 C13 C14 159.7(4) . . . . ?
C16 N6 C13 C14 2.3(6) . . . . ?
P2 N6 C16 C15 -161.8(4) . . . . ?
C13 N6 C16 C15 -5.1(6) . . . . ?
P3 N7 C17 C18 -131.4(6) . . . . ?
C20 N7 C17 C18 11.2(6) . . . . ?
P3 N7 C20 C19 143.2(4) . . . . ?
C17 N7 C20 C19 1.4(5) . . . . ?
P3 N8 C21 C22 -166.3(4) . . . . ?
C24 N8 C21 C22 -12.1(5) . . . . ?
P3 N8 C24 C23 159.0(3) . . . . ?
C21 N8 C24 C23 6.4(5) . . . . ?
C3 C2 C1 C2 0.1(2) . . . 2 ?
C4 C3 C2 C1 -0.3(5) . . . . ?
C5 C3 C2 C1 178.3(3) . . . . ?
C2 C3 C5 N4 37.9(4) . . . . ?
C4 C3 C5 N4 -143.5(2) . . . . ?
C3 C4 C3 C2 0.1(2) 2 . . . ?
C3 C4 C3 C5 -178.5(3) 2 . . . ?
N4 C6 C7 C8 -56.2(3) . . . . ?
O1 C8 C7 C6 60.7(3) . . . . ?
N5 C9 C10 C11 14.2(6) . . . . ?
C12 C11 C10 C9 -25.4(6) . . . . ?
N5 C12 C11 C10 26.3(5) . . . . ?
N6 C13 C14 C15 1.7(8) . . . . ?
C16 C15 C14 C13 -4.9(10) . . . . ?
C14 C15 C16 N6 6.2(8) . . . . ?
N7 C17 C18 C19 -20.1(9) . . . . ?
C20 C19 C18 C17 21.5(11) . . . . ?
N7 C20 C19 C18 -13.9(9) . . . . ?
C23 C22 C21 N8 13.3(6) . . . . ?
C21 C22 C23 C24 -9.7(7) . . . . ?
C22 C23 C24 N8 1.9(6) . . . . ?

_refine_diff_density_max         0.413
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.057

_shelxl_version_number           2013-4

