# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_423_rt
_database_code_depnum_ccdc_archive 'CCDC 1004560'
_audit_update_record             
;
2015-10-25 deposited with the CCDC.
2016-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H40 N2 O12 P4'
_chemical_formula_weight         648.44

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'
N N 0.0061 0.0033 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   19.5429(8)
_cell_length_b                   4.71970(10)
_cell_length_c                   17.2626(7)
_cell_angle_alpha                90
_cell_angle_beta                 114.668(5)
_cell_angle_gamma                90
_cell_volume                     1446.93(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    14489
_cell_measurement_theta_min      3.0653
_cell_measurement_theta_max      34.1190

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_F_000             684
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.574
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.034
_exptl_absorpt_coefficient_mu    0.324
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.88538
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Xcalibur-EOS
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19524
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.248
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2563
_reflns_number_gt                2430
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0100P)²+1.0000P] 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         2563
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0692
_refine_ls_wR_factor_gt          0.0686
_refine_ls_goodness_of_fit_ref   1.306
_refine_ls_restrained_S_all      1.306
_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 0.68439(3) 0.30047(11) 0.37313(3) 0.02598(13) Uani 1 1 d . . . . .
P2 P 1.18525(3) 0.02508(11) 0.78418(3) 0.03012(14) Uani 1 1 d . . . . .
O1 O 0.68478(7) 0.1944(3) 0.28999(8) 0.0322(3) Uani 1 1 d . . . . .
O6 O 1.17408(9) 0.2735(3) 0.83594(10) 0.0414(4) Uani 1 1 d . . . . .
H6 H 1.1920 0.4184 0.8258 0.062 Uiso 1 1 calc R U . . .
O2 O 0.63246(7) 0.5485(3) 0.36032(9) 0.0332(3) Uani 1 1 d . . . . .
O3 O 0.65984(9) 0.0548(3) 0.41652(9) 0.0381(4) Uani 1 1 d . . . . .
H3 H 0.6561 -0.0924 0.3898 0.057 Uiso 1 1 calc R U . . .
O5 O 1.22776(8) 0.1494(3) 0.73379(10) 0.0389(4) Uani 1 1 d . . . . .
H5 H 1.2544 0.0264 0.7270 0.058 Uiso 1 1 calc R U . . .
O4 O 1.22362(8) -0.2221(3) 0.83871(9) 0.0414(4) Uani 1 1 d . . . . .
C1 C 0.77732(11) 0.4014(4) 0.44627(13) 0.0350(5) Uani 1 1 d . . . . .
H1A H 0.7970 0.5331 0.4174 0.042 Uiso 1 1 calc R U . . .
H1B H 0.7735 0.5029 0.4931 0.042 Uiso 1 1 calc R U . . .
C2 C 0.83435(11) 0.1644(4) 0.48340(13) 0.0339(5) Uani 1 1 d . . . . .
H2B H 0.8387 0.0599 0.4373 0.041 Uiso 1 1 calc R U . . .
H2A H 0.8165 0.0346 0.5144 0.041 Uiso 1 1 calc R U . . .
C9 C 0.52484(10) 0.9017(4) 0.03370(12) 0.0287(4) Uani 1 1 d . . . . .
C3 C 0.91156(11) 0.2752(5) 0.54299(14) 0.0369(5) Uani 1 1 d . . . . .
H3A H 0.9329 0.3781 0.5097 0.044 Uiso 1 1 calc R U . . .
H3B H 0.9056 0.4077 0.5827 0.044 Uiso 1 1 calc R U . . .
C6 C 1.09346(11) -0.0774(5) 0.70996(14) 0.0373(5) Uani 1 1 d . . . . .
H6A H 1.0989 -0.2219 0.6730 0.045 Uiso 1 1 calc R U . . .
H6B H 1.0679 -0.1639 0.7415 0.045 Uiso 1 1 calc R U . . .
C4 C 0.96607(11) 0.0451(5) 0.59302(14) 0.0365(5) Uani 1 1 d . . . . .
H4A H 0.9727 -0.0853 0.5533 0.044 Uiso 1 1 calc R U . . .
H4B H 0.9442 -0.0603 0.6253 0.044 Uiso 1 1 calc R U . . .
C5 C 1.04298(11) 0.1551(5) 0.65409(14) 0.0377(5) Uani 1 1 d . . . . .
H5A H 1.0675 0.2421 0.6215 0.045 Uiso 1 1 calc R U . . .
H5B H 1.0363 0.3000 0.6902 0.045 Uiso 1 1 calc R U . . .
N1 N 0.61522(10) 0.5384(4) 0.15683(12) 0.0439(5) Uani 1 1 d . . . . .
H1 H 0.6437 0.4243 0.1958 0.053 Uiso 1 1 calc R U . . .
C8 C 0.58486(12) 0.7669(5) 0.02698(14) 0.0419(5) Uani 1 1 d . . . . .
H8C H 0.5954 0.8016 -0.0199 0.050 Uiso 1 1 calc R U . . .
C10 C 0.51235(12) 0.8467(5) 0.10564(14) 0.0425(5) Uani 1 1 d . . . . .
H10C H 0.4725 0.9332 0.1125 0.051 Uiso 1 1 calc R U . . .
C11 C 0.55881(14) 0.6653(6) 0.16641(15) 0.0504(6) Uani 1 1 d . . . . .
H11C H 0.5508 0.6305 0.2150 0.060 Uiso 1 1 calc R U . . .
C7 C 0.62895(12) 0.5824(5) 0.08903(15) 0.0460(6) Uani 1 1 d . . . . .
H7C H 0.6685 0.4883 0.0835 0.055 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 O2 1.5041(14) . ?
P1 O1 1.5230(14) . ?
P1 O3 1.5606(14) . ?
P1 C1 1.790(2) . ?
P2 O4 1.4901(15) . ?
P2 O6 1.5439(15) . ?
P2 O5 1.5474(15) . ?
P2 C6 1.782(2) . ?
O6 H6 0.8200 . ?
O3 H3 0.8200 . ?
O5 H5 0.8200 . ?
C1 C2 1.519(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.521(3) . ?
C2 H2B 0.9700 . ?
C2 H2A 0.9700 . ?
C9 C8 1.381(3) . ?
C9 C10 1.386(3) . ?
C9 C9 1.488(4) 3_675 ?
C3 C4 1.514(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C6 C5 1.521(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C4 C5 1.522(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
N1 C7 1.322(3) . ?
N1 C11 1.324(3) . ?
N1 H1 0.8600 . ?
C8 C7 1.370(3) . ?
C8 H8C 0.9300 . ?
C10 C11 1.365(3) . ?
C10 H10C 0.9300 . ?
C11 H11C 0.9300 . ?
C7 H7C 0.9300 . ?

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
O2 P1 O1 112.70(8) . . ?
O2 P1 O3 108.97(8) . . ?
O1 P1 O3 109.36(8) . . ?
O2 P1 C1 108.66(9) . . ?
O1 P1 C1 110.46(9) . . ?
O3 P1 C1 106.48(9) . . ?
O4 P2 O6 112.61(9) . . ?
O4 P2 O5 113.92(9) . . ?
O6 P2 O5 106.03(8) . . ?
O4 P2 C6 109.39(10) . . ?
O6 P2 C6 106.21(10) . . ?
O5 P2 C6 108.32(10) . . ?
P2 O6 H6 109.5 . . ?
P1 O3 H3 109.5 . . ?
P2 O5 H5 109.5 . . ?
C2 C1 P1 116.82(15) . . ?
C2 C1 H1A 108.1 . . ?
P1 C1 H1A 108.1 . . ?
C2 C1 H1B 108.1 . . ?
P1 C1 H1B 108.1 . . ?
H1A C1 H1B 107.3 . . ?
C1 C2 C3 112.22(17) . . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
H2B C2 H2A 107.9 . . ?
C8 C9 C10 117.53(19) . . ?
C8 C9 C9 121.4(2) . 3_675 ?
C10 C9 C9 121.0(2) . 3_675 ?
C4 C3 C2 113.73(18) . . ?
C4 C3 H3A 108.8 . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C5 C6 P2 116.87(15) . . ?
C5 C6 H6A 108.1 . . ?
P2 C6 H6A 108.1 . . ?
C5 C6 H6B 108.1 . . ?
P2 C6 H6B 108.1 . . ?
H6A C6 H6B 107.3 . . ?
C3 C4 C5 113.99(18) . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C5 C4 H4B 108.8 . . ?
H4A C4 H4B 107.6 . . ?
C6 C5 C4 112.62(18) . . ?
C6 C5 H5A 109.1 . . ?
C4 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C7 N1 C11 121.80(19) . . ?
C7 N1 H1 119.1 . . ?
C11 N1 H1 119.1 . . ?
C7 C8 C9 120.4(2) . . ?
C7 C8 H8C 119.8 . . ?
C9 C8 H8C 119.8 . . ?
C11 C10 C9 119.8(2) . . ?
C11 C10 H10C 120.1 . . ?
C9 C10 H10C 120.1 . . ?
N1 C11 C10 120.6(2) . . ?
N1 C11 H11C 119.7 . . ?
C10 C11 H11C 119.7 . . ?
N1 C7 C8 119.9(2) . . ?
N1 C7 H7C 120.1 . . ?
C8 C7 H7C 120.1 . . ?

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
O2 P1 C1 C2 166.44(15) . . . . ?
O1 P1 C1 C2 -69.45(18) . . . . ?
O3 P1 C1 C2 49.20(18) . . . . ?
P1 C1 C2 C3 178.73(15) . . . . ?
C1 C2 C3 C4 169.89(18) . . . . ?
O4 P2 C6 C5 174.56(16) . . . . ?
O6 P2 C6 C5 52.78(19) . . . . ?
O5 P2 C6 C5 -60.74(19) . . . . ?
C2 C3 C4 C5 -178.85(18) . . . . ?
P2 C6 C5 C4 179.91(15) . . . . ?
C3 C4 C5 C6 173.92(19) . . . . ?
C10 C9 C8 C7 1.2(3) . . . . ?
C9 C9 C8 C7 -178.7(2) 3_675 . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C9 C9 C10 C11 180.0(3) 3_675 . . . ?
C7 N1 C11 C10 0.3(4) . . . . ?
C9 C10 C11 N1 -0.8(4) . . . . ?
C11 N1 C7 C8 1.0(4) . . . . ?
C9 C8 C7 N1 -1.8(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.86 1.84 2.676(2) 164.3 .
O3 H3 O2 0.82 1.77 2.550(2) 157.3 1_545
O6 H6 O4 0.82 1.79 2.563(2) 157.1 1_565
O5 H5 O1 0.82 1.70 2.5117(19) 172.8 3_756

_refine_diff_density_max         0.351
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.042

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_exp_580_100
_database_code_depnum_ccdc_archive 'CCDC 1433066'
_audit_update_record             
;
2015-10-25 deposited with the CCDC.
2016-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H18 N2 O6 P2'
_chemical_formula_weight         360.23

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.8401(4)
_cell_length_b                   12.0388(5)
_cell_length_c                   15.2173(5)
_cell_angle_alpha                95.386(3)
_cell_angle_beta                 106.844(3)
_cell_angle_gamma                112.289(4)
_cell_volume                     1553.60(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9013
_cell_measurement_theta_min      2.8685
_cell_measurement_theta_max      29.6923

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.7164
_exptl_crystal_size_mid          0.0642
_exptl_crystal_size_min          0.0623
_exptl_absorpt_coefficient_mu    0.313
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93889
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Xcalibur-EOS
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19960
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.874
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7121
_reflns_number_gt                5468
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0300P)²+1.0000P] 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         7121
_refine_ls_number_parameters     422
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.0920
_refine_ls_wR_factor_gt          0.0851
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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 0.95707(6) 0.15487(5) 0.10792(4) 0.01252(12) Uani 1 1 d . . . . .
P2 P 0.38710(6) 0.17858(5) 0.06604(4) 0.01233(12) Uani 1 1 d . . . . .
O1 O 0.89774(15) 0.03469(13) 0.13749(10) 0.0150(3) Uani 1 1 d . . . . .
O6 O 0.34479(16) 0.15489(14) -0.04337(10) 0.0161(3) Uani 1 1 d . . . . .
H6 H 0.2658 0.0900 -0.0687 0.024 Uiso 1 1 calc R U . . .
O4 O 0.32127(16) 0.06216(13) 0.09784(10) 0.0158(3) Uani 1 1 d . . . . .
O3 O 0.92177(16) 0.13322(13) -0.00114(10) 0.0164(3) Uani 1 1 d . . . . .
H3 H 0.8464 0.0665 -0.0278 0.025 Uiso 1 1 calc R U . . .
O2 O 1.12938(15) 0.23734(14) 0.15806(10) 0.0173(3) Uani 1 1 d . . . . .
O5 O 0.33930(16) 0.27938(13) 0.09586(11) 0.0180(3) Uani 1 1 d . . . . .
H5 H 0.2622 0.2487 0.1112 0.027 Uiso 1 1 calc R U . . .
C2 C 0.6745(2) 0.16985(19) 0.08859(14) 0.0147(4) Uani 1 1 d . . . . .
H2A H 0.6430 0.1443 0.0207 0.018 Uiso 1 1 calc R U . . .
H2B H 0.6406 0.0964 0.1130 0.018 Uiso 1 1 calc R U . . .
C1 C 0.8528(2) 0.24051(19) 0.13194(14) 0.0152(4) Uani 1 1 d . . . . .
H1A H 0.8826 0.2656 0.1998 0.018 Uiso 1 1 calc R U . . .
H1B H 0.8848 0.3148 0.1083 0.018 Uiso 1 1 calc R U . . .
C3 C 0.5961(2) 0.25073(19) 0.11178(14) 0.0145(4) Uani 1 1 d . . . . .
H3A H 0.6318 0.3239 0.0873 0.017 Uiso 1 1 calc R U . . .
H3B H 0.6309 0.2772 0.1798 0.017 Uiso 1 1 calc R U . . .
P4 P 0.60521(6) 0.34550(5) 0.39768(4) 0.01446(12) Uani 1 1 d . . . . .
P3 P 0.05289(6) 0.31944(5) 0.43437(4) 0.01393(12) Uani 1 1 d . . . . .
O9 O 0.12448(16) 0.34508(14) 0.54386(10) 0.0172(3) Uani 1 1 d . . . . .
H9 H 0.2069 0.4081 0.5635 0.026 Uiso 1 1 calc R U . . .
O7 O 0.08224(16) 0.43774(13) 0.40085(10) 0.0173(3) Uani 1 1 d . . . . .
O11 O 0.68696(16) 0.36208(13) 0.50483(10) 0.0164(3) Uani 1 1 d . . . . .
H11 H 0.7605 0.4307 0.5264 0.025 Uiso 1 1 calc R U . . .
O8 O -0.11727(16) 0.22852(14) 0.40457(11) 0.0187(3) Uani 1 1 d . . . . .
O10 O 0.62658(16) 0.46710(14) 0.37134(10) 0.0185(3) Uani 1 1 d . . . . .
O12 O 0.65723(17) 0.26933(16) 0.34012(10) 0.0234(4) Uani 1 1 d . . . . .
H12 H 0.7358 0.2654 0.3746 0.035 Uiso 1 1 calc R U . . .
C4 C 0.1496(2) 0.24086(19) 0.38994(14) 0.0154(4) Uani 1 1 d . . . . .
H4A H 0.1390 0.1692 0.4165 0.018 Uiso 1 1 calc R U . . .
H4B H 0.0986 0.2121 0.3220 0.018 Uiso 1 1 calc R U . . .
C5 C 0.3236(2) 0.32253(19) 0.41322(15) 0.0156(4) Uani 1 1 d . . . . .
H5A H 0.3348 0.3953 0.3880 0.019 Uiso 1 1 calc R U . . .
H5B H 0.3757 0.3494 0.4812 0.019 Uiso 1 1 calc R U . . .
C6 C 0.4021(2) 0.25433(19) 0.37225(15) 0.0159(4) Uani 1 1 d . . . . .
H6A H 0.3492 0.2274 0.3044 0.019 Uiso 1 1 calc R U . . .
H6B H 0.3896 0.1813 0.3973 0.019 Uiso 1 1 calc R U . . .
N4 N 0.05386(19) 0.89555(16) 0.33095(12) 0.0169(4) Uani 1 1 d . . . . .
H4 H -0.0348 0.8938 0.3299 0.020 Uiso 1 1 calc R U . . .
N3 N 0.76325(19) 0.88856(17) 0.32785(12) 0.0176(4) Uani 1 1 d . . . . .
C19 C 0.4845(2) 0.89567(19) 0.33218(14) 0.0133(4) Uani 1 1 d . . . . .
C17 C 0.6764(2) 0.8146(2) 0.37037(15) 0.0179(4) Uani 1 1 d . . . . .
H17C H 0.7109 0.7602 0.3986 0.022 Uiso 1 1 calc R U . . .
C20 C 0.3348(2) 0.89763(18) 0.33303(14) 0.0124(4) Uani 1 1 d . . . . .
C21 C 0.2468(2) 0.93319(19) 0.26133(14) 0.0156(4) Uani 1 1 d . . . . .
H21C H 0.2831 0.9581 0.2132 0.019 Uiso 1 1 calc R U . . .
C22 C 0.1065(2) 0.93144(19) 0.26162(15) 0.0166(4) Uani 1 1 d . . . . .
H22C H 0.0480 0.9551 0.2137 0.020 Uiso 1 1 calc R U . . .
C18 C 0.5379(2) 0.8149(2) 0.37453(14) 0.0159(4) Uani 1 1 d . . . . .
H18C H 0.4814 0.7622 0.4051 0.019 Uiso 1 1 calc R U . . .
C25 C 0.5740(2) 0.97198(19) 0.28766(15) 0.0162(4) Uani 1 1 d . . . . .
H25C H 0.5417 1.0265 0.2582 0.019 Uiso 1 1 calc R U . . .
C23 C 0.1359(2) 0.8624(2) 0.40164(16) 0.0202(5) Uani 1 1 d . . . . .
H23C H 0.0975 0.8392 0.4493 0.024 Uiso 1 1 calc R U . . .
C26 C 0.7120(2) 0.9662(2) 0.28756(15) 0.0173(4) Uani 1 1 d . . . . .
H26C H 0.7715 1.0186 0.2582 0.021 Uiso 1 1 calc R U . . .
C24 C 0.2768(2) 0.8626(2) 0.40415(15) 0.0179(4) Uani 1 1 d . . . . .
H24C H 0.3333 0.8392 0.4533 0.021 Uiso 1 1 calc R U . . .
N2 N 0.72073(19) 0.59592(16) 0.16076(12) 0.0159(4) Uani 1 1 d . . . . .
H2 H 0.6332 0.5961 0.1602 0.019 Uiso 1 1 calc R U . . .
N1 N 1.44019(19) 0.60148(16) 0.16458(12) 0.0157(4) Uani 1 1 d . . . . .
C9 C 1.1551(2) 0.60046(19) 0.16541(14) 0.0133(4) Uani 1 1 d . . . . .
C10 C 1.0030(2) 0.59875(18) 0.16415(14) 0.0133(4) Uani 1 1 d . . . . .
C14 C 0.9432(2) 0.56275(19) 0.23491(14) 0.0155(4) Uani 1 1 d . . . . .
H14C H 0.9993 0.5396 0.2844 0.019 Uiso 1 1 calc R U . . .
C15 C 1.2437(2) 0.67747(19) 0.11997(14) 0.0153(4) Uani 1 1 d . . . . .
H15C H 1.2083 0.7293 0.0885 0.018 Uiso 1 1 calc R U . . .
C8 C 1.2159(2) 0.52609(19) 0.21186(15) 0.0156(4) Uani 1 1 d . . . . .
H8C H 1.1629 0.4753 0.2448 0.019 Uiso 1 1 calc R U . . .
C7 C 1.3561(2) 0.5285(2) 0.20850(15) 0.0173(4) Uani 1 1 d . . . . .
H7C H 1.3936 0.4766 0.2384 0.021 Uiso 1 1 calc R U . . .
C13 C 0.8014(2) 0.5616(2) 0.23126(14) 0.0161(4) Uani 1 1 d . . . . .
H13C H 0.7614 0.5368 0.2781 0.019 Uiso 1 1 calc R U . . .
C16 C 1.3841(2) 0.67585(19) 0.12221(14) 0.0160(4) Uani 1 1 d . . . . .
H16C H 1.4428 0.7290 0.0929 0.019 Uiso 1 1 calc R U . . .
C11 C 0.9130(2) 0.6314(2) 0.09131(15) 0.0189(5) Uani 1 1 d . . . . .
H11C H 0.9483 0.6543 0.0424 0.023 Uiso 1 1 calc R U . . .
C12 C 0.7730(2) 0.6299(2) 0.09115(16) 0.0202(5) Uani 1 1 d . . . . .
H12C H 0.7142 0.6526 0.0426 0.024 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 1.5068(15) . ?
P1 O2 1.5079(14) . ?
P1 O3 1.5681(14) . ?
P1 C1 1.788(2) . ?
P2 O4 1.4962(15) . ?
P2 O5 1.5339(15) . ?
P2 O6 1.5639(14) . ?
P2 C3 1.780(2) . ?
O6 H6 0.8200 . ?
O3 H3 0.8200 . ?
O5 H5 0.8200 . ?
C2 C3 1.526(3) . ?
C2 C1 1.527(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
P4 O10 1.5078(16) . ?
P4 O12 1.5281(15) . ?
P4 O11 1.5500(14) . ?
P4 C6 1.777(2) . ?
P3 O7 1.5106(15) . ?
P3 O8 1.5112(15) . ?
P3 O9 1.5575(15) . ?
P3 C4 1.787(2) . ?
O9 H9 0.8200 . ?
O11 H11 0.8200 . ?
O12 H12 0.8200 . ?
C4 C5 1.526(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.524(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
N4 C23 1.338(3) . ?
N4 C22 1.342(3) . ?
N4 H4 0.8600 . ?
N3 C26 1.338(3) . ?
N3 C17 1.339(3) . ?
C19 C25 1.389(3) . ?
C19 C18 1.395(3) . ?
C19 C20 1.486(3) . ?
C17 C18 1.384(3) . ?
C17 H17C 0.9300 . ?
C20 C24 1.391(3) . ?
C20 C21 1.395(3) . ?
C21 C22 1.373(3) . ?
C21 H21C 0.9300 . ?
C22 H22C 0.9300 . ?
C18 H18C 0.9300 . ?
C25 C26 1.386(3) . ?
C25 H25C 0.9300 . ?
C23 C24 1.375(3) . ?
C23 H23C 0.9300 . ?
C26 H26C 0.9300 . ?
C24 H24C 0.9300 . ?
N2 C13 1.338(3) . ?
N2 C12 1.339(3) . ?
N2 H2 0.8600 . ?
N1 C7 1.335(3) . ?
N1 C16 1.341(3) . ?
C9 C8 1.392(3) . ?
C9 C15 1.398(3) . ?
C9 C10 1.484(3) . ?
C10 C11 1.394(3) . ?
C10 C14 1.398(3) . ?
C14 C13 1.375(3) . ?
C14 H14C 0.9300 . ?
C15 C16 1.380(3) . ?
C15 H15C 0.9300 . ?
C8 C7 1.384(3) . ?
C8 H8C 0.9300 . ?
C7 H7C 0.9300 . ?
C13 H13C 0.9300 . ?
C16 H16C 0.9300 . ?
C11 C12 1.371(3) . ?
C11 H11C 0.9300 . ?
C12 H12C 0.9300 . ?

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 O2 115.07(8) . . ?
O1 P1 O3 111.48(8) . . ?
O2 P1 O3 108.49(8) . . ?
O1 P1 C1 108.64(9) . . ?
O2 P1 C1 106.69(9) . . ?
O3 P1 C1 105.98(9) . . ?
O4 P2 O5 115.08(8) . . ?
O4 P2 O6 112.30(8) . . ?
O5 P2 O6 107.86(8) . . ?
O4 P2 C3 112.32(9) . . ?
O5 P2 C3 104.44(9) . . ?
O6 P2 C3 103.98(9) . . ?
P2 O6 H6 109.5 . . ?
P1 O3 H3 109.5 . . ?
P2 O5 H5 109.5 . . ?
C3 C2 C1 110.40(17) . . ?
C3 C2 H2A 109.6 . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C2 C1 P1 114.23(14) . . ?
C2 C1 H1A 108.7 . . ?
P1 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
P1 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C2 C3 P2 114.97(14) . . ?
C2 C3 H3A 108.5 . . ?
P2 C3 H3A 108.5 . . ?
C2 C3 H3B 108.5 . . ?
P2 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
O10 P4 O12 112.89(9) . . ?
O10 P4 O11 112.05(8) . . ?
O12 P4 O11 110.75(8) . . ?
O10 P4 C6 108.98(9) . . ?
O12 P4 C6 105.67(9) . . ?
O11 P4 C6 106.06(9) . . ?
O7 P3 O8 115.65(8) . . ?
O7 P3 O9 111.55(8) . . ?
O8 P3 O9 107.28(8) . . ?
O7 P3 C4 109.38(9) . . ?
O8 P3 C4 106.57(9) . . ?
O9 P3 C4 105.86(9) . . ?
P3 O9 H9 109.5 . . ?
P4 O11 H11 109.5 . . ?
P4 O12 H12 109.5 . . ?
C5 C4 P3 112.65(15) . . ?
C5 C4 H4A 109.1 . . ?
P3 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
P3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C6 C5 C4 111.53(17) . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C5 C6 P4 113.29(15) . . ?
C5 C6 H6A 108.9 . . ?
P4 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
P4 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C23 N4 C22 121.59(17) . . ?
C23 N4 H4 119.2 . . ?
C22 N4 H4 119.2 . . ?
C26 N3 C17 117.60(18) . . ?
C25 C19 C18 117.82(18) . . ?
C25 C19 C20 121.29(18) . . ?
C18 C19 C20 120.88(18) . . ?
N3 C17 C18 123.39(19) . . ?
N3 C17 H17C 118.3 . . ?
C18 C17 H17C 118.3 . . ?
C24 C20 C21 117.91(18) . . ?
C24 C20 C19 121.37(17) . . ?
C21 C20 C19 120.71(18) . . ?
C22 C21 C20 120.12(19) . . ?
C22 C21 H21C 119.9 . . ?
C20 C21 H21C 119.9 . . ?
N4 C22 C21 120.07(18) . . ?
N4 C22 H22C 120.0 . . ?
C21 C22 H22C 120.0 . . ?
C17 C18 C19 118.86(19) . . ?
C17 C18 H18C 120.6 . . ?
C19 C18 H18C 120.6 . . ?
C26 C25 C19 119.44(19) . . ?
C26 C25 H25C 120.3 . . ?
C19 C25 H25C 120.3 . . ?
N4 C23 C24 120.34(19) . . ?
N4 C23 H23C 119.8 . . ?
C24 C23 H23C 119.8 . . ?
N3 C26 C25 122.9(2) . . ?
N3 C26 H26C 118.6 . . ?
C25 C26 H26C 118.6 . . ?
C23 C24 C20 119.95(19) . . ?
C23 C24 H24C 120.0 . . ?
C20 C24 H24C 120.0 . . ?
C13 N2 C12 121.60(18) . . ?
C13 N2 H2 119.2 . . ?
C12 N2 H2 119.2 . . ?
C7 N1 C16 117.26(17) . . ?
C8 C9 C15 117.23(18) . . ?
C8 C9 C10 121.66(18) . . ?
C15 C9 C10 121.11(18) . . ?
C11 C10 C14 117.47(18) . . ?
C11 C10 C9 121.06(18) . . ?
C14 C10 C9 121.47(17) . . ?
C13 C14 C10 119.94(18) . . ?
C13 C14 H14C 120.0 . . ?
C10 C14 H14C 120.0 . . ?
C16 C15 C9 119.40(19) . . ?
C16 C15 H15C 120.3 . . ?
C9 C15 H15C 120.3 . . ?
C7 C8 C9 119.35(19) . . ?
C7 C8 H8C 120.3 . . ?
C9 C8 H8C 120.3 . . ?
N1 C7 C8 123.41(19) . . ?
N1 C7 H7C 118.3 . . ?
C8 C7 H7C 118.3 . . ?
N2 C13 C14 120.38(19) . . ?
N2 C13 H13C 119.8 . . ?
C14 C13 H13C 119.8 . . ?
N1 C16 C15 123.30(19) . . ?
N1 C16 H16C 118.4 . . ?
C15 C16 H16C 118.4 . . ?
C12 C11 C10 120.51(19) . . ?
C12 C11 H11C 119.7 . . ?
C10 C11 H11C 119.7 . . ?
N2 C12 C11 120.09(19) . . ?
N2 C12 H12C 120.0 . . ?
C11 C12 H12C 120.0 . . ?

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 C2 C1 P1 -179.27(14) . . . . ?
O1 P1 C1 C2 -53.85(17) . . . . ?
O2 P1 C1 C2 -178.47(14) . . . . ?
O3 P1 C1 C2 66.05(17) . . . . ?
C1 C2 C3 P2 -179.48(14) . . . . ?
O4 P2 C3 C2 56.59(17) . . . . ?
O5 P2 C3 C2 -178.05(14) . . . . ?
O6 P2 C3 C2 -65.07(16) . . . . ?
O7 P3 C4 C5 53.29(16) . . . . ?
O8 P3 C4 C5 178.98(14) . . . . ?
O9 P3 C4 C5 -67.02(16) . . . . ?
P3 C4 C5 C6 -178.46(14) . . . . ?
C4 C5 C6 P4 -179.86(14) . . . . ?
O10 P4 C6 C5 -50.63(17) . . . . ?
O12 P4 C6 C5 -172.21(14) . . . . ?
O11 P4 C6 C5 70.17(16) . . . . ?
C26 N3 C17 C18 -0.1(3) . . . . ?
C25 C19 C20 C24 -154.3(2) . . . . ?
C18 C19 C20 C24 27.1(3) . . . . ?
C25 C19 C20 C21 26.7(3) . . . . ?
C18 C19 C20 C21 -152.0(2) . . . . ?
C24 C20 C21 C22 -0.8(3) . . . . ?
C19 C20 C21 C22 178.26(19) . . . . ?
C23 N4 C22 C21 0.9(3) . . . . ?
C20 C21 C22 N4 0.0(3) . . . . ?
N3 C17 C18 C19 0.3(3) . . . . ?
C25 C19 C18 C17 0.1(3) . . . . ?
C20 C19 C18 C17 178.73(19) . . . . ?
C18 C19 C25 C26 -0.6(3) . . . . ?
C20 C19 C25 C26 -179.24(19) . . . . ?
C22 N4 C23 C24 -1.0(3) . . . . ?
C17 N3 C26 C25 -0.5(3) . . . . ?
C19 C25 C26 N3 0.8(3) . . . . ?
N4 C23 C24 C20 0.2(3) . . . . ?
C21 C20 C24 C23 0.7(3) . . . . ?
C19 C20 C24 C23 -178.4(2) . . . . ?
C8 C9 C10 C11 -154.2(2) . . . . ?
C15 C9 C10 C11 26.0(3) . . . . ?
C8 C9 C10 C14 24.8(3) . . . . ?
C15 C9 C10 C14 -155.0(2) . . . . ?
C11 C10 C14 C13 -0.6(3) . . . . ?
C9 C10 C14 C13 -179.64(19) . . . . ?
C8 C9 C15 C16 0.6(3) . . . . ?
C10 C9 C15 C16 -179.58(18) . . . . ?
C15 C9 C8 C7 -2.1(3) . . . . ?
C10 C9 C8 C7 178.08(19) . . . . ?
C16 N1 C7 C8 0.2(3) . . . . ?
C9 C8 C7 N1 1.8(3) . . . . ?
C12 N2 C13 C14 1.3(3) . . . . ?
C10 C14 C13 N2 -0.6(3) . . . . ?
C7 N1 C16 C15 -1.8(3) . . . . ?
C9 C15 C16 N1 1.4(3) . . . . ?
C14 C10 C11 C12 1.2(3) . . . . ?
C9 C10 C11 C12 -179.7(2) . . . . ?
C13 N2 C12 C11 -0.6(3) . . . . ?
C10 C11 C12 N2 -0.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4 N3 0.86 1.96 2.815(2) 179.5 1_455
N2 H2 N1 0.86 1.94 2.804(2) 177.4 1_455
O5 H5 O2 0.82 1.63 2.4184(19) 160.3 1_455
O12 H12 O8 0.82 1.62 2.4048(19) 158.2 1_655
O11 H11 O7 0.82 1.72 2.517(2) 164.8 2_666
O9 H9 O10 0.82 1.68 2.489(2) 166.6 2_666
O3 H3 O4 0.82 1.73 2.542(2) 170.8 2_655
O6 H6 O1 0.82 1.68 2.496(2) 170.4 2_655

_refine_diff_density_max         0.431
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.066

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_exp_547_100
_database_code_depnum_ccdc_archive 'CCDC 1433067'
_audit_update_record             
;
2015-10-25 deposited with the CCDC.
2016-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H48 N2 O12 P4'
_chemical_formula_weight         704.54

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.1052(2)
_cell_length_b                   9.5324(3)
_cell_length_c                   20.3596(6)
_cell_angle_alpha                79.976(2)
_cell_angle_beta                 86.857(2)
_cell_angle_gamma                69.836(2)
_cell_volume                     1633.45(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    105(2)
_cell_measurement_reflns_used    19740
_cell_measurement_theta_min      2.8057
_cell_measurement_theta_max      31.8998

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_F_000             748
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.294
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.90238
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      105(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Xcalibur-EOS
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27285
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.811
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5745
_reflns_number_gt                5169
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0555P)²+0.5500P] 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         5745
_refine_ls_number_parameters     403
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0912
_refine_ls_wR_factor_gt          0.0883
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
P3 P 0.49121(5) 0.52288(5) 0.16720(2) 0.01094(11) Uani 1 1 d . . . . .
P4 P 0.89496(5) 0.07650(5) 0.73891(2) 0.01199(12) Uani 1 1 d . . . . .
P2 P 1.01142(5) 0.50641(5) 0.84713(2) 0.01131(12) Uani 1 1 d . . . . .
P1 P 0.64529(5) 0.85262(5) 0.27292(2) 0.01149(12) Uani 1 1 d . . . . .
O7 O 0.51857(13) 0.45677(13) 0.10374(6) 0.0147(3) Uani 1 1 d . . . . .
O9 O 0.31901(13) 0.58825(13) 0.18551(6) 0.0147(3) Uani 1 1 d . . . . .
O1 O 0.50758(13) 0.85845(13) 0.23231(6) 0.0149(3) Uani 1 1 d . . . . .
O4 O 0.83806(13) 0.53691(14) 0.87054(6) 0.0163(3) Uani 1 1 d . . . . .
H4 H 0.7960 0.4961 0.8489 0.024 Uiso 1 1 calc R U . . .
O12 O 0.77828(14) -0.01239(13) 0.74223(6) 0.0167(3) Uani 1 1 d . . . . .
H12 H 0.6907 0.0421 0.7514 0.025 Uiso 1 1 calc R U . . .
O6 O 1.09615(14) 0.54567(13) 0.89790(6) 0.0176(3) Uani 1 1 d . . . . .
O8 O 0.56550(14) 0.65080(13) 0.15730(6) 0.0159(3) Uani 1 1 d . . . . .
H8 H 0.5358 0.7021 0.1870 0.024 Uiso 1 1 calc R U . . .
O5 O 1.07861(14) 0.33733(13) 0.84023(6) 0.0143(3) Uani 1 1 d . . . . .
H5 H 1.1150 0.3292 0.8028 0.021 Uiso 1 1 calc R U . . .
O3 O 0.66899(14) 1.00992(13) 0.25200(6) 0.0175(3) Uani 1 1 d . . . . .
H3 H 0.7591 1.0011 0.2604 0.026 Uiso 1 1 calc R U . . .
O2 O 0.79515(14) 0.72398(13) 0.26605(6) 0.0161(3) Uani 1 1 d . . . . .
O11 O 1.05778(13) -0.03151(13) 0.73649(6) 0.0161(3) Uani 1 1 d . . . . .
N2 N 0.41532(16) 0.26632(15) 0.06399(7) 0.0134(3) Uani 1 1 d . . . . .
H2 H 0.4553 0.3251 0.0782 0.016 Uiso 1 1 calc R U . . .
O10 O 0.86998(15) 0.15299(13) 0.80211(6) 0.0180(3) Uani 1 1 d . . . . .
H10 H 0.7997 0.2355 0.7950 0.027 Uiso 1 1 calc R U . . .
N1 N 0.14200(16) -0.23951(16) -0.05901(7) 0.0151(3) Uani 1 1 d . . . . .
H1 H 0.1161 -0.3056 -0.0749 0.018 Uiso 1 1 calc R U . . .
C20 C 0.29058(19) 0.07623(18) 0.01809(8) 0.0126(3) Uani 1 1 d . . . . .
C13 C 0.7579(2) 0.2307(2) 0.47935(9) 0.0182(4) Uani 1 1 d . . . . .
H13A H 0.8633 0.1795 0.4650 0.022 Uiso 1 1 calc R U . . .
H13B H 0.7046 0.1571 0.4879 0.022 Uiso 1 1 calc R U . . .
C9 C 0.5887(2) 0.37857(18) 0.23506(8) 0.0137(4) Uani 1 1 d . . . . .
H9A H 0.5429 0.2993 0.2403 0.016 Uiso 1 1 calc R U . . .
H9B H 0.6976 0.3342 0.2232 0.016 Uiso 1 1 calc R U . . .
C11 C 0.6667(2) 0.3022(2) 0.35776(9) 0.0169(4) Uani 1 1 d . . . . .
H11A H 0.6136 0.2284 0.3650 0.020 Uiso 1 1 calc R U . . .
H11B H 0.7726 0.2521 0.3436 0.020 Uiso 1 1 calc R U . . .
C19 C 0.23169(18) -0.03079(18) -0.00834(8) 0.0123(3) Uani 1 1 d . . . . .
C15 C 0.8421(2) 0.1619(2) 0.60198(8) 0.0172(4) Uani 1 1 d . . . . .
H15A H 0.9492 0.1080 0.5905 0.021 Uiso 1 1 calc R U . . .
H15B H 0.7862 0.0905 0.6088 0.021 Uiso 1 1 calc R U . . .
C23 C 0.3629(2) 0.29957(19) 0.00139(8) 0.0153(4) Uani 1 1 d . . . . .
H23C H 0.3690 0.3862 -0.0261 0.018 Uiso 1 1 calc R U . . .
C16 C 0.8416(2) 0.22255(19) 0.66706(9) 0.0169(4) Uani 1 1 d . . . . .
H16A H 0.7379 0.2929 0.6737 0.020 Uiso 1 1 calc R U . . .
H16B H 0.9139 0.2781 0.6629 0.020 Uiso 1 1 calc R U . . .
C7 C 0.8804(2) 0.6204(2) 0.71984(8) 0.0162(4) Uani 1 1 d . . . . .
H7A H 0.8775 0.5188 0.7222 0.019 Uiso 1 1 calc R U . . .
H7B H 0.7799 0.6832 0.7346 0.019 Uiso 1 1 calc R U . . .
C10 C 0.5820(2) 0.43149(19) 0.30234(8) 0.0157(4) Uani 1 1 d . . . . .
H10A H 0.6292 0.5096 0.2979 0.019 Uiso 1 1 calc R U . . .
H10B H 0.4735 0.4757 0.3148 0.019 Uiso 1 1 calc R U . . .
C8 C 1.0091(2) 0.61578(19) 0.76627(8) 0.0139(4) Uani 1 1 d . . . . .
H8A H 0.9961 0.7187 0.7713 0.017 Uiso 1 1 calc R U . . .
H8B H 1.1096 0.5744 0.7454 0.017 Uiso 1 1 calc R U . . .
C12 C 0.6728(2) 0.3569(2) 0.42333(9) 0.0181(4) Uani 1 1 d . . . . .
H12A H 0.7245 0.4318 0.4158 0.022 Uiso 1 1 calc R U . . .
H12B H 0.5667 0.4064 0.4374 0.022 Uiso 1 1 calc R U . . .
C24 C 0.2997(2) 0.20651(19) -0.02291(8) 0.0151(4) Uani 1 1 d . . . . .
H24C H 0.2631 0.2305 -0.0666 0.018 Uiso 1 1 calc R U . . .
C14 C 0.7665(2) 0.2880(2) 0.54406(9) 0.0186(4) Uani 1 1 d . . . . .
H14A H 0.6614 0.3451 0.5567 0.022 Uiso 1 1 calc R U . . .
H14B H 0.8257 0.3566 0.5361 0.022 Uiso 1 1 calc R U . . .
C1 C 0.5905(2) 0.8363(2) 0.35918(9) 0.0175(4) Uani 1 1 d . . . . .
H1A H 0.5038 0.9268 0.3654 0.021 Uiso 1 1 calc R U . . .
H1B H 0.5539 0.7509 0.3703 0.021 Uiso 1 1 calc R U . . .
C6 C 0.9073(2) 0.6831(2) 0.64801(9) 0.0183(4) Uani 1 1 d . . . . .
H6A H 1.0023 0.6138 0.6320 0.022 Uiso 1 1 calc R U . . .
H6B H 0.9229 0.7791 0.6468 0.022 Uiso 1 1 calc R U . . .
C2 C 0.7219(2) 0.8151(2) 0.40757(9) 0.0202(4) Uani 1 1 d . . . . .
H2A H 0.8137 0.7326 0.3978 0.024 Uiso 1 1 calc R U . . .
H2B H 0.7490 0.9065 0.4008 0.024 Uiso 1 1 calc R U . . .
C3 C 0.6770(2) 0.7810(2) 0.48029(9) 0.0208(4) Uani 1 1 d . . . . .
H3A H 0.5877 0.8655 0.4905 0.025 Uiso 1 1 calc R U . . .
H3B H 0.6457 0.6921 0.4866 0.025 Uiso 1 1 calc R U . . .
C4 C 0.8094(2) 0.7536(2) 0.52851(9) 0.0221(4) Uani 1 1 d . . . . .
H4A H 0.8348 0.8456 0.5245 0.027 Uiso 1 1 calc R U . . .
H4B H 0.9013 0.6751 0.5157 0.027 Uiso 1 1 calc R U . . .
C21 C 0.3453(2) 0.0469(2) 0.08358(9) 0.0189(4) Uani 1 1 d . . . . .
H21C H 0.3400 -0.0382 0.1125 0.023 Uiso 1 1 calc R U . . .
C18 C 0.1905(2) -0.0089(2) -0.07512(9) 0.0238(4) Uani 1 1 d . . . . .
H18C H 0.1919 0.0783 -0.1036 0.029 Uiso 1 1 calc R U . . .
C5 C 0.7730(2) 0.7068(2) 0.60118(9) 0.0212(4) Uani 1 1 d . . . . .
H5A H 0.7499 0.6135 0.6057 0.025 Uiso 1 1 calc R U . . .
H5B H 0.6804 0.7843 0.6142 0.025 Uiso 1 1 calc R U . . .
C22 C 0.4071(2) 0.1435(2) 0.10528(9) 0.0189(4) Uani 1 1 d . . . . .
H22C H 0.4435 0.1236 0.1489 0.023 Uiso 1 1 calc R U . . .
C17 C 0.1478(2) -0.1155(2) -0.09929(9) 0.0219(4) Uani 1 1 d . . . . .
H17C H 0.1227 -0.1008 -0.1442 0.026 Uiso 1 1 calc R U . . .
C25 C 0.2204(2) -0.1603(2) 0.03223(9) 0.0220(4) Uani 1 1 d . . . . .
H25C H 0.2432 -0.1777 0.0775 0.026 Uiso 1 1 calc R U . . .
C26 C 0.1758(2) -0.2622(2) 0.00559(9) 0.0237(4) Uani 1 1 d . . . . .
H26C H 0.1692 -0.3486 0.0331 0.028 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
P3 O7 1.5061(12) . ?
P3 O9 1.5261(12) . ?
P3 O8 1.5663(12) . ?
P3 C9 1.7945(16) . ?
P4 O11 1.4892(12) . ?
P4 O10 1.5553(12) . ?
P4 O12 1.5633(12) . ?
P4 C16 1.7936(17) . ?
P2 O6 1.4917(12) . ?
P2 O5 1.5431(12) . ?
P2 O4 1.5661(12) . ?
P2 C8 1.7856(17) . ?
P1 O2 1.5068(12) . ?
P1 O1 1.5194(12) . ?
P1 O3 1.5706(12) . ?
P1 C1 1.7943(18) . ?
O4 H4 0.8200 . ?
O12 H12 0.8200 . ?
O8 H8 0.8200 . ?
O5 H5 0.8200 . ?
O3 H3 0.8200 . ?
N2 C23 1.332(2) . ?
N2 C22 1.339(2) . ?
N2 H2 0.8600 . ?
O10 H10 0.8200 . ?
N1 C26 1.331(2) . ?
N1 C17 1.332(2) . ?
N1 H1 0.8600 . ?
C20 C24 1.396(2) . ?
C20 C21 1.397(2) . ?
C20 C19 1.489(2) . ?
C13 C12 1.525(2) . ?
C13 C14 1.527(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C9 C10 1.531(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 C12 1.526(2) . ?
C11 C10 1.531(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C19 C18 1.391(2) . ?
C19 C25 1.393(2) . ?
C15 C14 1.528(2) . ?
C15 C16 1.534(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C23 C24 1.378(2) . ?
C23 H23C 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C7 C6 1.521(2) . ?
C7 C8 1.530(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C24 H24C 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C1 C2 1.528(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C6 C5 1.522(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C2 C3 1.524(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.519(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.522(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C21 C22 1.374(2) . ?
C21 H21C 0.9300 . ?
C18 C17 1.376(3) . ?
C18 H18C 0.9300 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C22 H22C 0.9300 . ?
C17 H17C 0.9300 . ?
C25 C26 1.372(3) . ?
C25 H25C 0.9300 . ?
C26 H26C 0.9300 . ?

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
O7 P3 O9 114.03(7) . . ?
O7 P3 O8 106.87(6) . . ?
O9 P3 O8 109.58(7) . . ?
O7 P3 C9 109.33(7) . . ?
O9 P3 C9 107.85(7) . . ?
O8 P3 C9 109.11(7) . . ?
O11 P4 O10 110.98(7) . . ?
O11 P4 O12 109.01(7) . . ?
O10 P4 O12 107.89(7) . . ?
O11 P4 C16 113.50(8) . . ?
O10 P4 C16 108.34(8) . . ?
O12 P4 C16 106.89(8) . . ?
O6 P2 O5 112.92(7) . . ?
O6 P2 O4 108.17(7) . . ?
O5 P2 O4 106.24(7) . . ?
O6 P2 C8 113.08(8) . . ?
O5 P2 C8 107.95(7) . . ?
O4 P2 C8 108.17(7) . . ?
O2 P1 O1 115.47(7) . . ?
O2 P1 O3 111.04(7) . . ?
O1 P1 O3 106.54(7) . . ?
O2 P1 C1 107.96(8) . . ?
O1 P1 C1 107.87(8) . . ?
O3 P1 C1 107.67(8) . . ?
P2 O4 H4 109.5 . . ?
P4 O12 H12 109.5 . . ?
P3 O8 H8 109.5 . . ?
P2 O5 H5 109.5 . . ?
P1 O3 H3 109.5 . . ?
C23 N2 C22 121.55(15) . . ?
C23 N2 H2 119.2 . . ?
C22 N2 H2 119.2 . . ?
P4 O10 H10 109.5 . . ?
C26 N1 C17 120.72(15) . . ?
C26 N1 H1 119.6 . . ?
C17 N1 H1 119.6 . . ?
C24 C20 C21 117.54(15) . . ?
C24 C20 C19 120.89(15) . . ?
C21 C20 C19 121.51(15) . . ?
C12 C13 C14 113.07(15) . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C10 C9 P3 115.51(12) . . ?
C10 C9 H9A 108.4 . . ?
P3 C9 H9A 108.4 . . ?
C10 C9 H9B 108.4 . . ?
P3 C9 H9B 108.4 . . ?
H9A C9 H9B 107.5 . . ?
C12 C11 C10 112.59(15) . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C18 C19 C25 116.92(16) . . ?
C18 C19 C20 121.61(15) . . ?
C25 C19 C20 121.44(15) . . ?
C14 C15 C16 112.46(14) . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
N2 C23 C24 120.43(15) . . ?
N2 C23 H23C 119.8 . . ?
C24 C23 H23C 119.8 . . ?
C15 C16 P4 113.37(12) . . ?
C15 C16 H16A 108.9 . . ?
P4 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
P4 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C6 C7 C8 111.57(14) . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C11 C10 C9 112.48(14) . . ?
C11 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C7 C8 P2 114.39(12) . . ?
C7 C8 H8A 108.7 . . ?
P2 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
P2 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C13 C12 C11 113.77(15) . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C23 C24 C20 120.02(16) . . ?
C23 C24 H24C 120.0 . . ?
C20 C24 H24C 120.0 . . ?
C13 C14 C15 113.76(15) . . ?
C13 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
C13 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C2 C1 P1 114.46(12) . . ?
C2 C1 H1A 108.6 . . ?
P1 C1 H1A 108.6 . . ?
C2 C1 H1B 108.6 . . ?
P1 C1 H1B 108.6 . . ?
H1A C1 H1B 107.6 . . ?
C7 C6 C5 113.56(15) . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C3 C2 C1 112.65(15) . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 C2 112.90(15) . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C3 C4 C5 114.26(16) . . ?
C3 C4 H4A 108.7 . . ?
C5 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C5 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C22 C21 C20 120.06(16) . . ?
C22 C21 H21C 120.0 . . ?
C20 C21 H21C 120.0 . . ?
C17 C18 C19 120.36(16) . . ?
C17 C18 H18C 119.8 . . ?
C19 C18 H18C 119.8 . . ?
C4 C5 C6 112.67(15) . . ?
C4 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
N2 C22 C21 120.41(16) . . ?
N2 C22 H22C 119.8 . . ?
C21 C22 H22C 119.8 . . ?
N1 C17 C18 120.69(16) . . ?
N1 C17 H17C 119.7 . . ?
C18 C17 H17C 119.7 . . ?
C26 C25 C19 120.21(17) . . ?
C26 C25 H25C 119.9 . . ?
C19 C25 H25C 119.9 . . ?
N1 C26 C25 121.03(16) . . ?
N1 C26 H26C 119.5 . . ?
C25 C26 H26C 119.5 . . ?

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
O7 P3 C9 C10 175.57(12) . . . . ?
O9 P3 C9 C10 -59.94(14) . . . . ?
O8 P3 C9 C10 59.03(14) . . . . ?
C24 C20 C19 C18 2.9(3) . . . . ?
C21 C20 C19 C18 -174.04(17) . . . . ?
C24 C20 C19 C25 -179.30(16) . . . . ?
C21 C20 C19 C25 3.7(3) . . . . ?
C22 N2 C23 C24 -0.7(3) . . . . ?
C14 C15 C16 P4 168.85(13) . . . . ?
O11 P4 C16 C15 63.22(15) . . . . ?
O10 P4 C16 C15 -173.03(12) . . . . ?
O12 P4 C16 C15 -57.00(14) . . . . ?
C12 C11 C10 C9 174.90(14) . . . . ?
P3 C9 C10 C11 179.65(12) . . . . ?
C6 C7 C8 P2 -166.81(12) . . . . ?
O6 P2 C8 C7 -159.85(12) . . . . ?
O5 P2 C8 C7 74.48(14) . . . . ?
O4 P2 C8 C7 -40.08(14) . . . . ?
C14 C13 C12 C11 178.55(15) . . . . ?
C10 C11 C12 C13 -179.42(15) . . . . ?
N2 C23 C24 C20 -0.1(3) . . . . ?
C21 C20 C24 C23 0.8(2) . . . . ?
C19 C20 C24 C23 -176.25(15) . . . . ?
C12 C13 C14 C15 176.27(15) . . . . ?
C16 C15 C14 C13 -177.15(15) . . . . ?
O2 P1 C1 C2 49.51(15) . . . . ?
O1 P1 C1 C2 174.92(13) . . . . ?
O3 P1 C1 C2 -70.45(15) . . . . ?
C8 C7 C6 C5 -173.43(15) . . . . ?
P1 C1 C2 C3 -172.42(13) . . . . ?
C1 C2 C3 C4 177.69(15) . . . . ?
C2 C3 C4 C5 -175.33(16) . . . . ?
C24 C20 C21 C22 -0.8(3) . . . . ?
C19 C20 C21 C22 176.29(16) . . . . ?
C25 C19 C18 C17 -2.8(3) . . . . ?
C20 C19 C18 C17 175.04(17) . . . . ?
C3 C4 C5 C6 -178.99(16) . . . . ?
C7 C6 C5 C4 -173.97(16) . . . . ?
C23 N2 C22 C21 0.7(3) . . . . ?
C20 C21 C22 N2 0.0(3) . . . . ?
C26 N1 C17 C18 0.7(3) . . . . ?
C19 C18 C17 N1 1.4(3) . . . . ?
C18 C19 C25 C26 2.3(3) . . . . ?
C20 C19 C25 C26 -175.59(17) . . . . ?
C17 N1 C26 C25 -1.2(3) . . . . ?
C19 C25 C26 N1 -0.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O7 0.86 1.71 2.5702(17) 174.3 .
O8 H8 O1 0.82 1.82 2.6026(16) 158.1 .
N1 H1 O6 0.86 1.68 2.5282(18) 170.3 1_444
O12 H12 O1 0.82 1.77 2.5846(16) 172.3 2_666
O10 H10 O9 0.82 1.76 2.5202(16) 154.5 2_666
O4 H4 O9 0.82 1.76 2.5691(16) 169.5 2_666
O5 H5 O2 0.82 1.65 2.4595(16) 168.3 2_766
O3 H3 O11 0.82 1.79 2.5923(16) 164.0 2_766

_refine_diff_density_max         0.408
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.049

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_no_311
_database_code_depnum_ccdc_archive 'CCDC 1433068'
_audit_update_record             
;
2015-10-25 deposited with the CCDC.
2016-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H52 N2 O12 P4'
_chemical_formula_weight         732.59

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           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -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'

_cell_length_a                   42.860(9)
_cell_length_b                   11.426(2)
_cell_length_c                   7.3826(15)
_cell_angle_alpha                90
_cell_angle_beta                 90.59(3)
_cell_angle_gamma                90
_cell_volume                     3615.2(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    12351
_cell_measurement_theta_min      2.020
_cell_measurement_theta_max      26.913

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             1560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.268
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.244
_exptl_absorpt_correction_T_max  0.267
_exptl_absorpt_process_details   shelxl

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Xcalibur-EOS
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26931
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -53
_diffrn_reflns_limit_h_max       54
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.020
_diffrn_reflns_theta_max         26.913
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.787
_diffrn_reflns_point_group_measured_fraction_full 0.831
_reflns_number_total             12351
_reflns_number_gt                11004
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.661
_reflns_Friedel_fraction_max     0.627
_reflns_Friedel_fraction_full    0.683

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0358P)²+3.3292P] 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_abs_structure_details 
;
 Flack x determined using 3796 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         12351
_refine_ls_number_parameters     841
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1079
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.131
_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 0.75522(4) 0.89158(13) 0.50954(18) 0.0241(3) Uani 1 1 d . . . . .
C1 C 0.78667(13) 0.8423(5) 0.6454(7) 0.0278(11) Uani 1 1 d . . . . .
H1A H 0.7817 0.8553 0.7717 0.033 Uiso 1 1 calc R U . . .
H1B H 0.7891 0.7586 0.6281 0.033 Uiso 1 1 calc R U . . .
O1 O 0.72443(9) 0.8430(3) 0.5819(5) 0.0305(9) Uani 1 1 d . . . . .
O9 O 1.10993(11) 0.4695(3) 0.0655(5) 0.0289(9) Uani 1 1 d . . . . .
H9 H 1.1093 0.4464 0.1705 0.043 Uiso 1 1 calc R U . . .
C9 C 1.02298(14) 0.8442(6) 0.7959(8) 0.0400(14) Uani 1 1 d . . . . .
H9A H 1.0224 0.7597 0.7831 0.048 Uiso 1 1 calc R U . . .
H9B H 1.0219 0.8623 0.9240 0.048 Uiso 1 1 calc R U . . .
N2 N 0.70489(13) 0.3604(4) 1.0125(6) 0.0290(11) Uani 1 1 d . . . . .
H2C H 0.7109 0.2892 1.0268 0.035 Uiso 1 1 calc R U . . .
O2 O 0.76159(10) 0.8583(3) 0.3122(5) 0.0331(9) Uani 1 1 d . . . . .
P2 P 1.05946(4) 0.89808(13) 0.70855(18) 0.0264(3) Uani 1 1 d . . . . .
C2 C 0.81796(13) 0.9034(5) 0.6035(7) 0.0313(12) Uani 1 1 d . . . . .
H2A H 0.8218 0.8980 0.4745 0.038 Uiso 1 1 calc R U . . .
H2B H 0.8163 0.9857 0.6342 0.038 Uiso 1 1 calc R U . . .
N3 N 0.15888(13) 1.1379(4) 0.6304(6) 0.0286(11) Uani 1 1 d . . . . .
H3C H 0.1526 1.2094 0.6258 0.034 Uiso 1 1 calc R U . . .
O3 O 0.75451(11) 1.0290(3) 0.5166(5) 0.0283(9) Uani 1 1 d . . . . .
H3 H 0.7572 1.0508 0.6214 0.043 Uiso 1 1 calc R U . . .
P3 P 1.10892(4) 0.60658(13) 0.06252(18) 0.0239(3) Uani 1 1 d . . . . .
C3 C 0.84561(14) 0.8510(6) 0.7061(8) 0.0381(14) Uani 1 1 d . . . . .
H3A H 0.8426 0.8619 0.8350 0.046 Uiso 1 1 calc R U . . .
H3B H 0.8464 0.7675 0.6828 0.046 Uiso 1 1 calc R U . . .
C39 C 0.67553(14) 0.7123(5) 0.9573(7) 0.0233(12) Uani 1 1 d . . . . .
C38 C 0.65008(14) 0.7440(5) 0.8519(7) 0.0259(12) Uani 1 1 d . . . . .
H38C H 0.6389 0.6871 0.7889 0.031 Uiso 1 1 calc R U . . .
C37 C 0.64127(15) 0.8596(6) 0.8399(8) 0.0283(13) Uani 1 1 d . . . . .
H37C H 0.6239 0.8802 0.7703 0.034 Uiso 1 1 calc R U . . .
C36 C 0.52410(15) 0.6027(7) -0.1533(8) 0.0350(14) Uani 1 1 d . . . . .
H36A H 0.5194 0.6303 -0.2748 0.042 Uiso 1 1 calc R U . . .
H36B H 0.5230 0.5179 -0.1551 0.042 Uiso 1 1 calc R U . . .
C35 C 0.49878(17) 0.6494(7) -0.0237(9) 0.0372(16) Uani 1 1 d . . . . .
H35A H 0.5046 0.6294 0.0997 0.045 Uiso 1 1 calc R U . . .
H35B H 0.4981 0.7341 -0.0323 0.045 Uiso 1 1 calc R U . . .
C34 C 0.46652(17) 0.6013(7) -0.0637(10) 0.0434(16) Uani 1 1 d . . . . .
H34A H 0.4668 0.5170 -0.0478 0.052 Uiso 1 1 calc R U . . .
H34B H 0.4612 0.6172 -0.1893 0.052 Uiso 1 1 calc R U . . .
C33 C 0.44118(17) 0.6537(7) 0.0582(10) 0.0419(17) Uani 1 1 d . . . . .
H33A H 0.4466 0.6375 0.1837 0.050 Uiso 1 1 calc R U . . .
H33B H 0.4410 0.7380 0.0427 0.050 Uiso 1 1 calc R U . . .
C32 C 0.40868(16) 0.6066(7) 0.0191(10) 0.0425(16) Uani 1 1 d . . . . .
H32A H 0.4089 0.5225 0.0363 0.051 Uiso 1 1 calc R U . . .
H32B H 0.4035 0.6216 -0.1070 0.051 Uiso 1 1 calc R U . . .
C7 C 0.96358(15) 0.8471(7) 0.7712(10) 0.0514(18) Uani 1 1 d . . . . .
H7A H 0.9631 0.7632 0.7511 0.062 Uiso 1 1 calc R U . . .
H7B H 0.9626 0.8604 0.9008 0.062 Uiso 1 1 calc R U . . .
P7 P 0.26089(4) 0.68361(13) 0.28521(18) 0.0245(3) Uani 1 1 d . . . . .
O7 O 1.13908(10) 0.6541(3) 0.1407(5) 0.0326(9) Uani 1 1 d . . . . .
O10 O 0.80295(12) 0.6385(3) -0.0397(5) 0.0394(11) Uani 1 1 d . . . . .
C10 C 1.07628(12) 0.6542(4) 0.1974(7) 0.0255(11) Uani 1 1 d . . . . .
H10A H 1.0807 0.6374 0.3238 0.031 Uiso 1 1 calc R U . . .
H10B H 1.0740 0.7383 0.1850 0.031 Uiso 1 1 calc R U . . .
C29 C 0.32476(16) 0.6704(6) 0.2064(9) 0.0351(15) Uani 1 1 d . . . . .
H29A H 0.3279 0.6476 0.3318 0.042 Uiso 1 1 calc R U . . .
H29B H 0.3264 0.7549 0.1997 0.042 Uiso 1 1 calc R U . . .
O11 O 0.77542(9) 0.6457(3) 0.2656(5) 0.0316(9) Uani 1 1 d . . . . .
H11 H 0.7751 0.7174 0.2634 0.047 Uiso 1 1 calc R U . . .
C11 C 1.04577(13) 0.5957(5) 0.1435(8) 0.0334(12) Uani 1 1 d . . . . .
H11A H 1.0472 0.5127 0.1699 0.040 Uiso 1 1 calc R U . . .
H11B H 1.0427 0.6042 0.0138 0.040 Uiso 1 1 calc R U . . .
O12 O 0.80304(10) 0.4653(3) 0.1690(5) 0.0323(9) Uani 1 1 d . . . . .
H12 H 0.8015 0.4464 0.2757 0.048 Uiso 1 1 calc R U . . .
C12 C 1.01719(14) 0.6465(6) 0.2416(8) 0.0391(14) Uani 1 1 d . . . . .
H12A H 1.0195 0.6326 0.3706 0.047 Uiso 1 1 calc R U . . .
H12B H 1.0165 0.7305 0.2226 0.047 Uiso 1 1 calc R U . . .
O22 O 0.57283(12) 0.5803(4) 0.0732(6) 0.0345(10) Uani 1 1 d . . . . .
C22 C 0.48123(17) 0.8413(7) 0.4859(10) 0.0423(17) Uani 1 1 d . . . . .
H22A H 0.4767 0.8587 0.3597 0.051 Uiso 1 1 calc R U . . .
H22B H 0.4806 0.7569 0.5000 0.051 Uiso 1 1 calc R U . . .
O13 O 0.63434(10) 0.8518(4) 0.4161(5) 0.0303(10) Uani 1 1 d . . . . .
C13 C 0.98701(15) 0.5939(7) 0.1766(10) 0.0469(17) Uani 1 1 d . . . . .
H13A H 0.9873 0.5106 0.2023 0.056 Uiso 1 1 calc R U . . .
H13B H 0.9855 0.6032 0.0462 0.056 Uiso 1 1 calc R U . . .
C14 C 0.95770(14) 0.6474(7) 0.2623(9) 0.0475(16) Uani 1 1 d . . . . .
H14A H 0.9583 0.6329 0.3917 0.057 Uiso 1 1 calc R U . . .
H14B H 0.9580 0.7315 0.2441 0.057 Uiso 1 1 calc R U . . .
O16 O 0.29128(12) 0.9201(4) 0.5485(5) 0.0334(10) Uani 1 1 d . . . . .
C16 C 0.89807(15) 0.6511(7) 0.2630(10) 0.0496(17) Uani 1 1 d . . . . .
H16A H 0.8978 0.6360 0.3922 0.059 Uiso 1 1 calc R U . . .
H16B H 0.8985 0.7353 0.2460 0.059 Uiso 1 1 calc R U . . .
O15 O 0.60299(12) 0.6810(4) 0.3295(6) 0.0333(10) Uani 1 1 d . . . . .
H15 H 0.5914 0.6593 0.2472 0.050 Uiso 1 1 calc R U . . .
C15 C 0.92753(15) 0.5987(7) 0.1845(10) 0.0503(17) Uani 1 1 d . . . . .
H15A H 0.9272 0.5148 0.2046 0.060 Uiso 1 1 calc R U . . .
H15B H 0.9273 0.6115 0.0546 0.060 Uiso 1 1 calc R U . . .
P5 P 0.60344(4) 0.81716(13) 0.33629(18) 0.0237(3) Uani 1 1 d . . . . .
C5 C 0.90446(16) 0.8511(6) 0.7457(10) 0.0482(16) Uani 1 1 d . . . . .
H5A H 0.9043 0.7675 0.7235 0.058 Uiso 1 1 calc R U . . .
H5B H 0.9028 0.8630 0.8754 0.058 Uiso 1 1 calc R U . . .
C56 C 0.18879(15) 1.1157(5) 0.6649(7) 0.0293(13) Uani 1 1 d . . . . .
H56C H 0.2026 1.1772 0.6843 0.035 Uiso 1 1 calc R U . . .
C55 C 0.19943(16) 1.0022(5) 0.6723(7) 0.0278(13) Uani 1 1 d . . . . .
H55C H 0.2205 0.9877 0.6952 0.033 Uiso 1 1 calc R U . . .
C54 C 0.17315(14) 0.6960(5) 0.5706(8) 0.0278(12) Uani 1 1 d . . . . .
H54C H 0.1559 0.7137 0.4980 0.033 Uiso 1 1 calc R U . . .
C53 C 0.18295(15) 0.5823(5) 0.5892(8) 0.0282(13) Uani 1 1 d . . . . .
H53C H 0.1724 0.5229 0.5282 0.034 Uiso 1 1 calc R U . . .
C52 C 0.22298(16) 0.6393(5) 0.7825(8) 0.0295(13) Uani 1 1 d . . . . .
H52C H 0.2401 0.6186 0.8540 0.035 Uiso 1 1 calc R U . . .
C51 C 0.21422(15) 0.7547(5) 0.7702(8) 0.0287(13) Uani 1 1 d . . . . .
H51C H 0.2250 0.8120 0.8345 0.034 Uiso 1 1 calc R U . . .
C50 C 0.18908(14) 0.7842(5) 0.6607(7) 0.0249(12) Uani 1 1 d . . . . .
O5 O 1.05946(11) 1.0322(3) 0.7261(5) 0.0355(9) Uani 1 1 d . . . . .
H5 H 1.0599 1.0503 0.8336 0.053 Uiso 1 1 calc R U . . .
C25 C 0.39774(17) 0.8978(8) 0.6839(9) 0.0447(17) Uani 1 1 d . . . . .
H25A H 0.4029 0.8814 0.8096 0.054 Uiso 1 1 calc R U . . .
H25B H 0.3976 0.9822 0.6691 0.054 Uiso 1 1 calc R U . . .
C26 C 0.36519(17) 0.8518(7) 0.6444(9) 0.0383(16) Uani 1 1 d . . . . .
H26A H 0.3655 0.7670 0.6518 0.046 Uiso 1 1 calc R U . . .
H26B H 0.3593 0.8729 0.5214 0.046 Uiso 1 1 calc R U . . .
C27 C 0.34031(15) 0.8988(7) 0.7746(8) 0.0354(14) Uani 1 1 d . . . . .
H27A H 0.3413 0.9836 0.7754 0.042 Uiso 1 1 calc R U . . .
H27B H 0.3452 0.8718 0.8962 0.042 Uiso 1 1 calc R U . . .
P8 P 0.56284(4) 0.64515(14) -0.09485(18) 0.0256(3) Uani 1 1 d . . . . .
C8 C 0.99473(15) 0.8960(6) 0.7003(10) 0.0468(16) Uani 1 1 d . . . . .
H8A H 0.9961 0.8799 0.5716 0.056 Uiso 1 1 calc R U . . .
H8B H 0.9949 0.9803 0.7161 0.056 Uiso 1 1 calc R U . . .
O8 O 1.10348(10) 0.6415(3) -0.1329(5) 0.0318(9) Uani 1 1 d . . . . .
O21 O 0.26195(12) 0.8207(3) 0.2926(6) 0.0309(9) Uani 1 1 d . . . . .
H21 H 0.2704 0.8416 0.3873 0.046 Uiso 1 1 calc R U . . .
C21 C 0.51414(16) 0.8840(6) 0.5309(9) 0.0360(15) Uani 1 1 d . . . . .
H21A H 0.5148 0.9683 0.5161 0.043 Uiso 1 1 calc R U . . .
H21B H 0.5187 0.8669 0.6571 0.043 Uiso 1 1 calc R U . . .
P4 P 0.80394(4) 0.59997(13) 0.15411(18) 0.0260(3) Uani 1 1 d . . . . .
C4 C 0.87633(15) 0.9055(6) 0.6528(10) 0.0460(16) Uani 1 1 d . . . . .
H4A H 0.8758 0.9883 0.6814 0.055 Uiso 1 1 calc R U . . .
H4B H 0.8787 0.8981 0.5227 0.055 Uiso 1 1 calc R U . . .
C49 C 0.17898(14) 0.9090(5) 0.6457(7) 0.0246(12) Uani 1 1 d . . . . .
C48 C 0.14766(15) 0.9349(5) 0.6107(8) 0.0283(13) Uani 1 1 d . . . . .
H48C H 0.1333 0.8750 0.5932 0.034 Uiso 1 1 calc R U . . .
C47 C 0.13819(16) 1.0513(6) 0.6025(8) 0.0328(14) Uani 1 1 d . . . . .
H47C H 0.1174 1.0693 0.5774 0.039 Uiso 1 1 calc R U . . .
C46 C 0.68162(15) 0.9159(6) 1.0305(8) 0.0315(14) Uani 1 1 d . . . . .
H46C H 0.6923 0.9751 1.0913 0.038 Uiso 1 1 calc R U . . .
C45 C 0.69120(14) 0.8017(5) 1.0488(8) 0.0283(13) Uani 1 1 d . . . . .
H45C H 0.7082 0.7839 1.1228 0.034 Uiso 1 1 calc R U . . .
C44 C 0.66458(15) 0.4961(5) 0.9473(7) 0.0267(13) Uani 1 1 d . . . . .
H44C H 0.6438 0.5105 0.9168 0.032 Uiso 1 1 calc R U . . .
C43 C 0.67534(15) 0.3822(5) 0.9672(7) 0.0276(13) Uani 1 1 d . . . . .
H43C H 0.6617 0.3201 0.9486 0.033 Uiso 1 1 calc R U . . .
C42 C 0.72513(14) 0.4470(5) 1.0361(8) 0.0278(12) Uani 1 1 d . . . . .
H42C H 0.7457 0.4297 1.0665 0.033 Uiso 1 1 calc R U . . .
C41 C 0.71627(15) 0.5617(5) 1.0163(8) 0.0283(13) Uani 1 1 d . . . . .
H41C H 0.7309 0.6212 1.0313 0.034 Uiso 1 1 calc R U . . .
C40 C 0.68547(14) 0.5892(5) 0.9739(7) 0.0245(12) Uani 1 1 d . . . . .
O4 O 1.06414(13) 0.8623(4) 0.5158(5) 0.0410(11) Uani 1 1 d . . . . .
P6 P 0.30154(4) 0.85471(14) 0.71659(18) 0.0270(3) Uani 1 1 d . . . . .
C6 C 0.93531(16) 0.9011(7) 0.6827(10) 0.0516(17) Uani 1 1 d . . . . .
H6A H 0.9367 0.8905 0.5527 0.062 Uiso 1 1 calc R U . . .
H6B H 0.9355 0.9846 0.7065 0.062 Uiso 1 1 calc R U . . .
O6 O 1.08560(9) 0.8512(3) 0.8335(5) 0.0304(8) Uani 1 1 d . . . . .
H6 H 1.0884 0.7815 0.8127 0.046 Uiso 1 1 calc R U . . .
N1 N 0.65735(12) 0.9420(4) 0.9271(6) 0.0268(11) Uani 1 1 d . . . . .
H1C H 0.6518 1.0139 0.9158 0.032 Uiso 1 1 calc R U . . .
C31 C 0.38293(18) 0.6593(7) 0.1373(10) 0.0446(18) Uani 1 1 d . . . . .
H31A H 0.3875 0.6411 0.2632 0.054 Uiso 1 1 calc R U . . .
H31B H 0.3833 0.7437 0.1244 0.054 Uiso 1 1 calc R U . . .
C23 C 0.45572(19) 0.8950(8) 0.6021(11) 0.0491(17) Uani 1 1 d . . . . .
H23A H 0.4609 0.8818 0.7286 0.059 Uiso 1 1 calc R U . . .
H23B H 0.4554 0.9788 0.5821 0.059 Uiso 1 1 calc R U . . .
O23 O 0.56395(11) 0.7771(4) -0.0720(5) 0.0325(10) Uani 1 1 d . . . . .
C24 C 0.42339(19) 0.8465(7) 0.5641(10) 0.0459(18) Uani 1 1 d . . . . .
H24A H 0.4239 0.7623 0.5809 0.055 Uiso 1 1 calc R U . . .
H24B H 0.4180 0.8615 0.4383 0.055 Uiso 1 1 calc R U . . .
O24 O 0.58438(11) 0.6150(4) -0.2617(5) 0.0358(11) Uani 1 1 d . . . . .
H24 H 0.5774 0.5576 -0.3149 0.054 Uiso 1 1 calc R U . . .
C28 C 0.29232(15) 0.6334(6) 0.1452(8) 0.0296(14) Uani 1 1 d . . . . .
H28A H 0.2916 0.5486 0.1405 0.035 Uiso 1 1 calc R U . . .
H28B H 0.2888 0.6621 0.0230 0.035 Uiso 1 1 calc R U . . .
N4 N 0.20720(13) 0.5567(4) 0.6929(6) 0.0294(11) Uani 1 1 d . . . . .
H4C H 0.2130 0.4849 0.7030 0.035 Uiso 1 1 calc R U . . .
C30 C 0.35055(17) 0.6151(7) 0.0901(10) 0.0416(17) Uani 1 1 d . . . . .
H30A H 0.3501 0.5309 0.1057 0.050 Uiso 1 1 calc R U . . .
H30B H 0.3462 0.6318 -0.0365 0.050 Uiso 1 1 calc R U . . .
O14 O 0.59898(11) 0.8682(4) 0.1474(5) 0.0325(10) Uani 1 1 d . . . . .
H14 H 0.5838 0.8375 0.0982 0.049 Uiso 1 1 calc R U . . .
C17 C 0.86838(14) 0.6030(6) 0.1779(9) 0.0431(15) Uani 1 1 d . . . . .
H17A H 0.8682 0.5187 0.1925 0.052 Uiso 1 1 calc R U . . .
H17B H 0.8685 0.6197 0.0491 0.052 Uiso 1 1 calc R U . . .
O17 O 0.30033(11) 0.7230(4) 0.6939(5) 0.0328(10) Uani 1 1 d . . . . .
C18 C 0.83822(14) 0.6538(5) 0.2596(8) 0.0349(13) Uani 1 1 d . . . . .
H18A H 0.8386 0.7384 0.2484 0.042 Uiso 1 1 calc R U . . .
H18B H 0.8377 0.6349 0.3876 0.042 Uiso 1 1 calc R U . . .
O18 O 0.28017(11) 0.8844(4) 0.8839(5) 0.0342(10) Uani 1 1 d . . . . .
H18 H 0.2839 0.9511 0.9189 0.051 Uiso 1 1 calc R U . . .
C19 C 0.57202(16) 0.8669(6) 0.4775(8) 0.0305(14) Uani 1 1 d . . . . .
H19A H 0.5756 0.8377 0.5993 0.037 Uiso 1 1 calc R U . . .
H19B H 0.5727 0.9517 0.4830 0.037 Uiso 1 1 calc R U . . .
O19 O 0.26563(11) 0.6318(3) 0.4740(5) 0.0296(10) Uani 1 1 d . . . . .
H19 H 0.2754 0.6783 0.5375 0.044 Uiso 1 1 calc R U . . .
C20 C 0.53941(16) 0.8301(6) 0.4158(9) 0.0363(15) Uani 1 1 d . . . . .
H20A H 0.5362 0.8535 0.2906 0.044 Uiso 1 1 calc R U . . .
H20B H 0.5378 0.7455 0.4216 0.044 Uiso 1 1 calc R U . . .
O20 O 0.23005(11) 0.6497(4) 0.2052(6) 0.0306(10) Uani 1 1 d . . . . .


_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 1.533(4) . ?
P1 O2 1.533(4) . ?
P1 O3 1.571(4) . ?
P1 C1 1.764(6) . ?
C1 C2 1.546(8) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
O9 P3 1.567(4) . ?
O9 H9 0.8200 . ?
C9 C8 1.516(9) . ?
C9 P2 1.805(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
N2 C42 1.327(8) . ?
N2 C43 1.330(8) . ?
N2 H2C 0.8600 . ?
P2 O4 1.496(4) . ?
P2 O5 1.538(4) . ?
P2 O6 1.540(4) . ?
C2 C3 1.523(8) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
N3 C56 1.329(8) . ?
N3 C47 1.343(8) . ?
N3 H3C 0.8600 . ?
O3 H3 0.8200 . ?
P3 O7 1.512(4) . ?
P3 O8 1.513(4) . ?
P3 C10 1.809(5) . ?
C3 C4 1.512(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C39 C38 1.381(8) . ?
C39 C45 1.393(8) . ?
C39 C40 1.475(8) . ?
C38 C37 1.377(8) . ?
C38 H38C 0.9300 . ?
C37 N1 1.329(8) . ?
C37 H37C 0.9300 . ?
C36 C35 1.549(9) . ?
C36 P8 1.778(7) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C35 C34 1.514(10) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C34 C33 1.539(9) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C33 C32 1.518(10) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C32 C31 1.536(10) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C7 C6 1.503(9) . ?
C7 C8 1.544(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
P7 O20 1.493(5) . ?
P7 O19 1.526(4) . ?
P7 O21 1.567(4) . ?
P7 C28 1.800(6) . ?
O10 P4 1.497(4) . ?
C10 C11 1.518(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C29 C28 1.518(9) . ?
C29 C30 1.542(9) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
O11 P4 1.570(4) . ?
O11 H11 0.8200 . ?
C11 C12 1.543(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
O12 P4 1.543(4) . ?
O12 H12 0.8200 . ?
C12 C13 1.501(9) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
O22 P8 1.504(4) . ?
C22 C23 1.526(10) . ?
C22 C21 1.526(10) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
O13 P5 1.497(5) . ?
C13 C14 1.539(8) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.515(9) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
O16 P6 1.510(4) . ?
C16 C17 1.516(9) . ?
C16 C15 1.518(8) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
O15 P5 1.557(4) . ?
O15 H15 0.8200 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
P5 O14 1.522(4) . ?
P5 C19 1.803(6) . ?
C5 C4 1.515(9) . ?
C5 C6 1.518(9) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C56 C55 1.375(8) . ?
C56 H56C 0.9300 . ?
C55 C49 1.392(8) . ?
C55 H55C 0.9300 . ?
C54 C53 1.371(8) . ?
C54 C50 1.384(8) . ?
C54 H54C 0.9300 . ?
C53 N4 1.317(8) . ?
C53 H53C 0.9300 . ?
C52 N4 1.332(8) . ?
C52 C51 1.374(9) . ?
C52 H52C 0.9300 . ?
C51 C50 1.382(9) . ?
C51 H51C 0.9300 . ?
C50 C49 1.494(8) . ?
O5 H5 0.8200 . ?
C25 C26 1.516(10) . ?
C25 C24 1.535(10) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.540(9) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 P6 1.785(7) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
P8 O23 1.518(4) . ?
P8 O24 1.585(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
O21 H21 0.8200 . ?
C21 C20 1.514(9) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
P4 C18 1.766(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C49 C48 1.396(9) . ?
C48 C47 1.392(8) . ?
C48 H48C 0.9300 . ?
C47 H47C 0.9300 . ?
C46 N1 1.318(8) . ?
C46 C45 1.375(9) . ?
C46 H46C 0.9300 . ?
C45 H45C 0.9300 . ?
C44 C43 1.388(8) . ?
C44 C40 1.403(8) . ?
C44 H44C 0.9300 . ?
C43 H43C 0.9300 . ?
C42 C41 1.372(8) . ?
C42 H42C 0.9300 . ?
C41 C40 1.389(8) . ?
C41 H41C 0.9300 . ?
P6 O17 1.515(4) . ?
P6 O18 1.582(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
O6 H6 0.8200 . ?
N1 H1C 0.8600 . ?
C31 C30 1.514(10) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C23 C24 1.516(11) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
O24 H24 0.8200 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
N4 H4C 0.8600 . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
O14 H14 0.8200 . ?
C17 C18 1.545(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
O18 H18 0.8200 . ?
C19 C20 1.525(9) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
O19 H19 0.8200 . ?
C20 H20A 0.9700 . ?
C20 H20B 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 O2 113.8(2) . . ?
O1 P1 O3 109.4(2) . . ?
O2 P1 O3 106.5(2) . . ?
O1 P1 C1 110.0(2) . . ?
O2 P1 C1 108.6(2) . . ?
O3 P1 C1 108.4(3) . . ?
C2 C1 P1 113.6(4) . . ?
C2 C1 H1A 108.8 . . ?
P1 C1 H1A 108.8 . . ?
C2 C1 H1B 108.8 . . ?
P1 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
P3 O9 H9 109.5 . . ?
C8 C9 P2 113.0(4) . . ?
C8 C9 H9A 109.0 . . ?
P2 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
P2 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C42 N2 C43 120.8(5) . . ?
C42 N2 H2C 119.6 . . ?
C43 N2 H2C 119.6 . . ?
O4 P2 O5 110.7(2) . . ?
O4 P2 O6 111.7(3) . . ?
O5 P2 O6 107.3(2) . . ?
O4 P2 C9 111.8(3) . . ?
O5 P2 C9 108.0(3) . . ?
O6 P2 C9 107.1(3) . . ?
C3 C2 C1 113.3(5) . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C56 N3 C47 121.5(5) . . ?
C56 N3 H3C 119.3 . . ?
C47 N3 H3C 119.3 . . ?
P1 O3 H3 109.5 . . ?
O7 P3 O8 113.1(2) . . ?
O7 P3 O9 109.3(2) . . ?
O8 P3 O9 106.3(2) . . ?
O7 P3 C10 110.2(2) . . ?
O8 P3 C10 109.5(2) . . ?
O9 P3 C10 108.3(2) . . ?
C4 C3 C2 112.6(5) . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C38 C39 C45 117.1(5) . . ?
C38 C39 C40 121.5(5) . . ?
C45 C39 C40 121.4(5) . . ?
C37 C38 C39 120.1(6) . . ?
C37 C38 H38C 119.9 . . ?
C39 C38 H38C 119.9 . . ?
N1 C37 C38 120.5(6) . . ?
N1 C37 H37C 119.7 . . ?
C38 C37 H37C 119.7 . . ?
C35 C36 P8 114.5(5) . . ?
C35 C36 H36A 108.6 . . ?
P8 C36 H36A 108.6 . . ?
C35 C36 H36B 108.6 . . ?
P8 C36 H36B 108.6 . . ?
H36A C36 H36B 107.6 . . ?
C34 C35 C36 113.5(5) . . ?
C34 C35 H35A 108.9 . . ?
C36 C35 H35A 108.9 . . ?
C34 C35 H35B 108.9 . . ?
C36 C35 H35B 108.9 . . ?
H35A C35 H35B 107.7 . . ?
C35 C34 C33 113.1(6) . . ?
C35 C34 H34A 108.9 . . ?
C33 C34 H34A 108.9 . . ?
C35 C34 H34B 108.9 . . ?
C33 C34 H34B 108.9 . . ?
H34A C34 H34B 107.8 . . ?
C32 C33 C34 113.8(6) . . ?
C32 C33 H33A 108.8 . . ?
C34 C33 H33A 108.8 . . ?
C32 C33 H33B 108.8 . . ?
C34 C33 H33B 108.8 . . ?
H33A C33 H33B 107.7 . . ?
C33 C32 C31 114.6(6) . . ?
C33 C32 H32A 108.6 . . ?
C31 C32 H32A 108.6 . . ?
C33 C32 H32B 108.6 . . ?
C31 C32 H32B 108.6 . . ?
H32A C32 H32B 107.6 . . ?
C6 C7 C8 113.6(6) . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
C8 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
O20 P7 O19 111.7(3) . . ?
O20 P7 O21 107.3(3) . . ?
O19 P7 O21 110.6(2) . . ?
O20 P7 C28 110.8(3) . . ?
O19 P7 C28 107.9(3) . . ?
O21 P7 C28 108.5(3) . . ?
C11 C10 P3 113.1(4) . . ?
C11 C10 H10A 109.0 . . ?
P3 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
P3 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C28 C29 C30 112.3(5) . . ?
C28 C29 H29A 109.1 . . ?
C30 C29 H29A 109.1 . . ?
C28 C29 H29B 109.1 . . ?
C30 C29 H29B 109.1 . . ?
H29A C29 H29B 107.9 . . ?
P4 O11 H11 109.5 . . ?
C10 C11 C12 113.4(5) . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
P4 O12 H12 109.5 . . ?
C13 C12 C11 112.7(5) . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C23 C22 C21 114.5(6) . . ?
C23 C22 H22A 108.6 . . ?
C21 C22 H22A 108.6 . . ?
C23 C22 H22B 108.6 . . ?
C21 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
C12 C13 C14 114.5(6) . . ?
C12 C13 H13A 108.6 . . ?
C14 C13 H13A 108.6 . . ?
C12 C13 H13B 108.6 . . ?
C14 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C15 C14 C13 113.3(6) . . ?
C15 C14 H14A 108.9 . . ?
C13 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C17 C16 C15 113.4(6) . . ?
C17 C16 H16A 108.9 . . ?
C15 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
P5 O15 H15 109.5 . . ?
C14 C15 C16 114.8(6) . . ?
C14 C15 H15A 108.6 . . ?
C16 C15 H15A 108.6 . . ?
C14 C15 H15B 108.6 . . ?
C16 C15 H15B 108.6 . . ?
H15A C15 H15B 107.5 . . ?
O13 P5 O14 111.2(3) . . ?
O13 P5 O15 106.7(3) . . ?
O14 P5 O15 110.6(2) . . ?
O13 P5 C19 110.6(3) . . ?
O14 P5 C19 108.7(3) . . ?
O15 P5 C19 108.9(3) . . ?
C4 C5 C6 113.5(6) . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
C6 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
N3 C56 C55 120.5(6) . . ?
N3 C56 H56C 119.8 . . ?
C55 C56 H56C 119.8 . . ?
C56 C55 C49 120.5(6) . . ?
C56 C55 H55C 119.8 . . ?
C49 C55 H55C 119.8 . . ?
C53 C54 C50 119.5(6) . . ?
C53 C54 H54C 120.2 . . ?
C50 C54 H54C 120.2 . . ?
N4 C53 C54 120.5(6) . . ?
N4 C53 H53C 119.8 . . ?
C54 C53 H53C 119.8 . . ?
N4 C52 C51 120.7(6) . . ?
N4 C52 H52C 119.7 . . ?
C51 C52 H52C 119.7 . . ?
C52 C51 C50 118.9(6) . . ?
C52 C51 H51C 120.5 . . ?
C50 C51 H51C 120.5 . . ?
C51 C50 C54 118.8(6) . . ?
C51 C50 C49 120.0(5) . . ?
C54 C50 C49 121.2(6) . . ?
P2 O5 H5 109.5 . . ?
C26 C25 C24 114.8(6) . . ?
C26 C25 H25A 108.6 . . ?
C24 C25 H25A 108.6 . . ?
C26 C25 H25B 108.6 . . ?
C24 C25 H25B 108.6 . . ?
H25A C25 H25B 107.5 . . ?
C25 C26 C27 113.6(6) . . ?
C25 C26 H26A 108.8 . . ?
C27 C26 H26A 108.8 . . ?
C25 C26 H26B 108.8 . . ?
C27 C26 H26B 108.8 . . ?
H26A C26 H26B 107.7 . . ?
C26 C27 P6 113.6(5) . . ?
C26 C27 H27A 108.8 . . ?
P6 C27 H27A 108.8 . . ?
C26 C27 H27B 108.8 . . ?
P6 C27 H27B 108.8 . . ?
H27A C27 H27B 107.7 . . ?
O22 P8 O23 112.9(2) . . ?
O22 P8 O24 111.8(3) . . ?
O23 P8 O24 106.6(2) . . ?
O22 P8 C36 108.8(3) . . ?
O23 P8 C36 109.0(3) . . ?
O24 P8 C36 107.6(3) . . ?
C9 C8 C7 113.0(6) . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
P7 O21 H21 109.5 . . ?
C20 C21 C22 114.3(6) . . ?
C20 C21 H21A 108.7 . . ?
C22 C21 H21A 108.7 . . ?
C20 C21 H21B 108.7 . . ?
C22 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
O10 P4 O12 111.1(2) . . ?
O10 P4 O11 112.9(3) . . ?
O12 P4 O11 105.9(2) . . ?
O10 P4 C18 109.5(3) . . ?
O12 P4 C18 109.7(3) . . ?
O11 P4 C18 107.6(2) . . ?
C3 C4 C5 113.9(6) . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C5 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C55 C49 C48 117.9(6) . . ?
C55 C49 C50 122.6(6) . . ?
C48 C49 C50 119.6(5) . . ?
C47 C48 C49 119.3(6) . . ?
C47 C48 H48C 120.3 . . ?
C49 C48 H48C 120.3 . . ?
N3 C47 C48 120.4(6) . . ?
N3 C47 H47C 119.8 . . ?
C48 C47 H47C 119.8 . . ?
N1 C46 C45 120.3(6) . . ?
N1 C46 H46C 119.8 . . ?
C45 C46 H46C 119.8 . . ?
C46 C45 C39 120.4(6) . . ?
C46 C45 H45C 119.8 . . ?
C39 C45 H45C 119.8 . . ?
C43 C44 C40 119.0(6) . . ?
C43 C44 H44C 120.5 . . ?
C40 C44 H44C 120.5 . . ?
N2 C43 C44 121.1(6) . . ?
N2 C43 H43C 119.4 . . ?
C44 C43 H43C 119.4 . . ?
N2 C42 C41 121.3(6) . . ?
N2 C42 H42C 119.4 . . ?
C41 C42 H42C 119.4 . . ?
C42 C41 C40 120.1(6) . . ?
C42 C41 H41C 120.0 . . ?
C40 C41 H41C 120.0 . . ?
C41 C40 C44 117.6(6) . . ?
C41 C40 C39 120.5(5) . . ?
C44 C40 C39 121.9(6) . . ?
O16 P6 O17 113.0(2) . . ?
O16 P6 O18 111.7(3) . . ?
O17 P6 O18 106.2(2) . . ?
O16 P6 C27 108.7(3) . . ?
O17 P6 C27 109.7(3) . . ?
O18 P6 C27 107.3(3) . . ?
C7 C6 C5 114.4(6) . . ?
C7 C6 H6A 108.7 . . ?
C5 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
C5 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
P2 O6 H6 109.5 . . ?
C46 N1 C37 121.5(5) . . ?
C46 N1 H1C 119.2 . . ?
C37 N1 H1C 119.2 . . ?
C30 C31 C32 113.6(6) . . ?
C30 C31 H31A 108.8 . . ?
C32 C31 H31A 108.8 . . ?
C30 C31 H31B 108.8 . . ?
C32 C31 H31B 108.8 . . ?
H31A C31 H31B 107.7 . . ?
C24 C23 C22 114.1(7) . . ?
C24 C23 H23A 108.7 . . ?
C22 C23 H23A 108.7 . . ?
C24 C23 H23B 108.7 . . ?
C22 C23 H23B 108.7 . . ?
H23A C23 H23B 107.6 . . ?
C23 C24 C25 114.4(6) . . ?
C23 C24 H24A 108.7 . . ?
C25 C24 H24A 108.7 . . ?
C23 C24 H24B 108.7 . . ?
C25 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
P8 O24 H24 109.5 . . ?
C29 C28 P7 115.4(4) . . ?
C29 C28 H28A 108.4 . . ?
P7 C28 H28A 108.4 . . ?
C29 C28 H28B 108.4 . . ?
P7 C28 H28B 108.4 . . ?
H28A C28 H28B 107.5 . . ?
C53 N4 C52 121.6(5) . . ?
C53 N4 H4C 119.2 . . ?
C52 N4 H4C 119.2 . . ?
C31 C30 C29 113.4(6) . . ?
C31 C30 H30A 108.9 . . ?
C29 C30 H30A 108.9 . . ?
C31 C30 H30B 108.9 . . ?
C29 C30 H30B 108.9 . . ?
H30A C30 H30B 107.7 . . ?
P5 O14 H14 109.5 . . ?
C16 C17 C18 113.8(5) . . ?
C16 C17 H17A 108.8 . . ?
C18 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 P4 113.1(4) . . ?
C17 C18 H18A 109.0 . . ?
P4 C18 H18A 109.0 . . ?
C17 C18 H18B 109.0 . . ?
P4 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
P6 O18 H18 109.5 . . ?
C20 C19 P5 115.3(4) . . ?
C20 C19 H19A 108.4 . . ?
P5 C19 H19A 108.4 . . ?
C20 C19 H19B 108.4 . . ?
P5 C19 H19B 108.4 . . ?
H19A C19 H19B 107.5 . . ?
P7 O19 H19 109.5 . . ?
C21 C20 C19 112.2(5) . . ?
C21 C20 H20A 109.2 . . ?
C19 C20 H20A 109.2 . . ?
C21 C20 H20B 109.2 . . ?
C19 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?

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
O1 P1 C1 C2 -170.0(4) . . . . ?
O2 P1 C1 C2 64.8(4) . . . . ?
O3 P1 C1 C2 -50.4(5) . . . . ?
C8 C9 P2 O4 -64.6(6) . . . . ?
C8 C9 P2 O5 57.4(6) . . . . ?
C8 C9 P2 O6 172.7(5) . . . . ?
P1 C1 C2 C3 -173.5(4) . . . . ?
C1 C2 C3 C4 175.6(5) . . . . ?
C45 C39 C38 C37 0.3(8) . . . . ?
C40 C39 C38 C37 179.6(5) . . . . ?
C39 C38 C37 N1 1.0(8) . . . . ?
P8 C36 C35 C34 -173.6(5) . . . . ?
C36 C35 C34 C33 -176.6(6) . . . . ?
C35 C34 C33 C32 179.7(7) . . . . ?
C34 C33 C32 C31 -179.1(7) . . . . ?
O7 P3 C10 C11 -171.6(4) . . . . ?
O8 P3 C10 C11 63.4(4) . . . . ?
O9 P3 C10 C11 -52.1(5) . . . . ?
P3 C10 C11 C12 -173.0(4) . . . . ?
C10 C11 C12 C13 175.7(5) . . . . ?
C11 C12 C13 C14 -176.4(6) . . . . ?
C12 C13 C14 C15 175.9(6) . . . . ?
C13 C14 C15 C16 -178.8(6) . . . . ?
C17 C16 C15 C14 178.2(6) . . . . ?
C47 N3 C56 C55 0.3(8) . . . . ?
N3 C56 C55 C49 -0.7(8) . . . . ?
C50 C54 C53 N4 0.5(9) . . . . ?
N4 C52 C51 C50 -1.2(8) . . . . ?
C52 C51 C50 C54 1.5(8) . . . . ?
C52 C51 C50 C49 179.7(5) . . . . ?
C53 C54 C50 C51 -1.2(8) . . . . ?
C53 C54 C50 C49 -179.3(5) . . . . ?
C24 C25 C26 C27 176.3(6) . . . . ?
C25 C26 C27 P6 174.9(5) . . . . ?
C35 C36 P8 O22 71.2(6) . . . . ?
C35 C36 P8 O23 -52.4(6) . . . . ?
C35 C36 P8 O24 -167.6(5) . . . . ?
P2 C9 C8 C7 178.3(5) . . . . ?
C6 C7 C8 C9 177.8(6) . . . . ?
C23 C22 C21 C20 179.7(7) . . . . ?
C2 C3 C4 C5 -177.2(6) . . . . ?
C6 C5 C4 C3 176.4(6) . . . . ?
C56 C55 C49 C48 0.3(8) . . . . ?
C56 C55 C49 C50 -177.1(5) . . . . ?
C51 C50 C49 C55 27.0(8) . . . . ?
C54 C50 C49 C55 -154.9(6) . . . . ?
C51 C50 C49 C48 -150.5(5) . . . . ?
C54 C50 C49 C48 27.6(8) . . . . ?
C55 C49 C48 C47 0.5(8) . . . . ?
C50 C49 C48 C47 178.0(5) . . . . ?
C56 N3 C47 C48 0.6(8) . . . . ?
C49 C48 C47 N3 -0.9(9) . . . . ?
N1 C46 C45 C39 0.5(9) . . . . ?
C38 C39 C45 C46 -1.0(8) . . . . ?
C40 C39 C45 C46 179.7(5) . . . . ?
C42 N2 C43 C44 -1.5(8) . . . . ?
C40 C44 C43 N2 0.6(8) . . . . ?
C43 N2 C42 C41 0.6(8) . . . . ?
N2 C42 C41 C40 1.1(9) . . . . ?
C42 C41 C40 C44 -1.9(8) . . . . ?
C42 C41 C40 C39 178.3(5) . . . . ?
C43 C44 C40 C41 1.1(8) . . . . ?
C43 C44 C40 C39 -179.2(5) . . . . ?
C38 C39 C40 C41 154.6(5) . . . . ?
C45 C39 C40 C41 -26.1(8) . . . . ?
C38 C39 C40 C44 -25.1(8) . . . . ?
C45 C39 C40 C44 154.1(5) . . . . ?
C26 C27 P6 O16 -71.8(6) . . . . ?
C26 C27 P6 O17 52.3(6) . . . . ?
C26 C27 P6 O18 167.3(5) . . . . ?
C8 C7 C6 C5 177.9(7) . . . . ?
C4 C5 C6 C7 -179.1(7) . . . . ?
C45 C46 N1 C37 0.8(8) . . . . ?
C38 C37 N1 C46 -1.6(8) . . . . ?
C33 C32 C31 C30 177.4(7) . . . . ?
C21 C22 C23 C24 -176.5(7) . . . . ?
C22 C23 C24 C25 178.5(7) . . . . ?
C26 C25 C24 C23 178.8(7) . . . . ?
C30 C29 C28 P7 174.9(5) . . . . ?
O20 P7 C28 C29 175.8(5) . . . . ?
O19 P7 C28 C29 -61.6(6) . . . . ?
O21 P7 C28 C29 58.3(6) . . . . ?
C54 C53 N4 C52 -0.1(9) . . . . ?
C51 C52 N4 C53 0.4(9) . . . . ?
C32 C31 C30 C29 -178.7(7) . . . . ?
C28 C29 C30 C31 174.7(6) . . . . ?
C15 C16 C17 C18 178.7(6) . . . . ?
C16 C17 C18 P4 178.2(5) . . . . ?
O10 P4 C18 C17 -64.1(5) . . . . ?
O12 P4 C18 C17 58.1(5) . . . . ?
O11 P4 C18 C17 172.9(4) . . . . ?
O13 P5 C19 C20 -176.4(5) . . . . ?
O14 P5 C19 C20 61.3(5) . . . . ?
O15 P5 C19 C20 -59.4(5) . . . . ?
C22 C21 C20 C19 -174.7(6) . . . . ?
P5 C19 C20 C21 -174.8(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O14 H14 O23 0.82 1.66 2.431(6) 155.6 .
O15 H15 O22 0.82 1.75 2.554(6) 164.9 .
O21 H21 O16 0.82 1.73 2.528(6) 163.3 .
O19 H19 O17 0.82 1.65 2.426(6) 157.7 .
O11 H11 O2 0.82 1.75 2.524(5) 156.9 .
O5 H5 O4 0.82 1.68 2.462(6) 157.5 2_575
O3 H3 O2 0.82 1.76 2.550(5) 161.5 2_575
N1 H1C O13 0.86 1.71 2.555(6) 168.6 2_575
O18 H18 O16 0.82 1.78 2.585(6) 165.9 2_575
O6 H6 O8 0.82 1.77 2.527(5) 152.8 1_556
O9 H9 O8 0.82 1.78 2.580(5) 163.1 2_565
O12 H12 O10 0.82 1.67 2.456(5) 158.8 2_565
N2 H2C O1 0.86 1.67 2.521(6) 172.2 2_565
N4 H4C O20 0.86 1.70 2.556(7) 170.3 2_565
O24 H24 O22 0.82 1.79 2.588(6) 164.5 2_564
N3 H3C O7 0.86 1.67 2.524(6) 173.5 2_475

_refine_diff_density_max         0.332
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.052

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_exp_1045_rt
_database_code_depnum_ccdc_archive 'CCDC 1433181'
_audit_update_record             
;
2015-10-25 deposited with the CCDC.
2016-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H40 N2 O12 P4'
_chemical_formula_weight         648.44

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.1687(4)
_cell_length_b                   9.6050(4)
_cell_length_c                   17.9827(7)
_cell_angle_alpha                79.130(3)
_cell_angle_beta                 89.668(3)
_cell_angle_gamma                70.320(3)
_cell_volume                     1461.54(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    10371
_cell_measurement_theta_min      3.0276
_cell_measurement_theta_max      30.8194

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_F_000             684
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.321
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91989
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Xcalibur-EOS
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15954
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.034
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5133
_reflns_number_gt                4390
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0459P)²+0.6092P] 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         5133
_refine_ls_number_parameters     367
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0930
_refine_ls_wR_factor_gt          0.0875
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.67988(6) 0.83067(6) 0.30949(3) 0.02583(14) Uani 1 1 d . . . . .
P2 P 0.99439(6) 0.52021(6) 0.82595(3) 0.02597(14) Uani 1 1 d . . . . .
P3 P 0.50651(6) 0.51010(6) 0.19030(3) 0.02404(14) Uani 1 1 d . . . . .
P4 P 0.86017(6) 0.10013(6) 0.70315(3) 0.02697(14) Uani 1 1 d . . . . .
O1 O 0.53742(17) 0.84076(17) 0.26350(8) 0.0348(4) Uani 1 1 d . . . . .
O2 O 0.82485(18) 0.70261(16) 0.30169(8) 0.0371(4) Uani 1 1 d . . . . .
O3 O 0.70478(18) 0.98556(16) 0.28561(10) 0.0400(4) Uani 1 1 d . . . . .
H3 H 0.7963 0.9742 0.2939 0.060 Uiso 1 1 calc R U . . .
O4 O 0.82686(17) 0.54644(18) 0.85207(9) 0.0382(4) Uani 1 1 d . . . . .
H4 H 0.7830 0.5066 0.8275 0.057 Uiso 1 1 calc R U . . .
O5 O 1.06045(18) 0.35499(15) 0.81778(8) 0.0324(3) Uani 1 1 d . . . . .
H5 H 1.0905 0.3507 0.7750 0.049 Uiso 1 1 calc R U . . .
O6 O 1.08405(19) 0.55531(18) 0.88435(9) 0.0422(4) Uani 1 1 d . . . . .
O7 O 0.52511(17) 0.45069(16) 0.11802(8) 0.0332(4) Uani 1 1 d . . . . .
O8 O 0.58045(19) 0.63684(17) 0.17957(8) 0.0366(4) Uani 1 1 d . . . . .
H8 H 0.5540 0.6861 0.2130 0.055 Uiso 1 1 calc R U . . .
O9 O 0.33942(16) 0.57339(16) 0.21096(8) 0.0333(3) Uani 1 1 d . . . . .
O10 O 0.8449(2) 0.17128(17) 0.77470(8) 0.0421(4) Uani 1 1 d . . . . .
H10 H 0.7754 0.2537 0.7665 0.063 Uiso 1 1 calc R U . . .
O11 O 1.01987(17) -0.00521(16) 0.69986(9) 0.0354(4) Uani 1 1 d . . . . .
O12 O 0.74488(18) 0.01128(17) 0.70777(9) 0.0380(4) Uani 1 1 d . . . . .
H12 H 0.6584 0.0660 0.7158 0.057 Uiso 1 1 calc R U . . .
N1 N 0.1355(2) -0.23356(19) -0.06728(10) 0.0341(4) Uani 1 1 d . . . . .
H1 H 0.1068 -0.2978 -0.0852 0.041 Uiso 1 1 calc R U . . .
N2 N 0.4184(2) 0.26358(19) 0.07212(10) 0.0303(4) Uani 1 1 d . . . . .
H2 H 0.4588 0.3218 0.0885 0.036 Uiso 1 1 calc R U . . .
C1 C 0.6382(3) 0.8088(3) 0.40735(12) 0.0405(6) Uani 1 1 d . . . . .
H1A H 0.5532 0.8977 0.4141 0.049 Uiso 1 1 calc R U . . .
H1B H 0.6031 0.7231 0.4203 0.049 Uiso 1 1 calc R U . . .
C2 C 0.7725(3) 0.7858(3) 0.46249(13) 0.0443(6) Uani 1 1 d . . . . .
H2A H 0.7949 0.8789 0.4566 0.053 Uiso 1 1 calc R U . . .
H2B H 0.8638 0.7089 0.4500 0.053 Uiso 1 1 calc R U . . .
C3 C 0.7403(3) 0.7391(3) 0.54471(13) 0.0464(6) Uani 1 1 d . . . . .
H3A H 0.6499 0.8168 0.5573 0.056 Uiso 1 1 calc R U . . .
H3B H 0.7160 0.6470 0.5503 0.056 Uiso 1 1 calc R U . . .
C4 C 0.8739(3) 0.7134(3) 0.59992(13) 0.0450(6) Uani 1 1 d . . . . .
H4A H 0.8876 0.8092 0.5999 0.054 Uiso 1 1 calc R U . . .
H4B H 0.9678 0.6478 0.5826 0.054 Uiso 1 1 calc R U . . .
C5 C 0.8535(3) 0.6440(3) 0.68028(12) 0.0393(5) Uani 1 1 d . . . . .
H5A H 0.8521 0.5430 0.6817 0.047 Uiso 1 1 calc R U . . .
H5B H 0.7544 0.7034 0.6962 0.047 Uiso 1 1 calc R U . . .
C6 C 0.9827(3) 0.6364(2) 0.73523(12) 0.0338(5) Uani 1 1 d . . . . .
H6A H 0.9684 0.7379 0.7420 0.041 Uiso 1 1 calc R U . . .
H6B H 1.0809 0.5997 0.7124 0.041 Uiso 1 1 calc R U . . .
C7 C 0.6109(3) 0.3619(2) 0.26698(12) 0.0319(5) Uani 1 1 d . . . . .
H7A H 0.5657 0.2829 0.2725 0.038 Uiso 1 1 calc R U . . .
H7B H 0.7172 0.3193 0.2536 0.038 Uiso 1 1 calc R U . . .
C8 C 0.6134(3) 0.4079(2) 0.34349(11) 0.0338(5) Uani 1 1 d . . . . .
H8A H 0.5074 0.4531 0.3567 0.041 Uiso 1 1 calc R U . . .
H8B H 0.6628 0.4836 0.3391 0.041 Uiso 1 1 calc R U . . .
C9 C 0.6991(3) 0.2757(2) 0.40704(12) 0.0356(5) Uani 1 1 d . . . . .
H9A H 0.6450 0.2035 0.4143 0.043 Uiso 1 1 calc R U . . .
H9B H 0.8026 0.2256 0.3922 0.043 Uiso 1 1 calc R U . . .
C10 C 0.7115(3) 0.3251(3) 0.48170(12) 0.0378(5) Uani 1 1 d . . . . .
H10A H 0.7692 0.3942 0.4746 0.045 Uiso 1 1 calc R U . . .
H10B H 0.6080 0.3796 0.4949 0.045 Uiso 1 1 calc R U . . .
C11 C 0.7900(3) 0.1957(2) 0.54746(12) 0.0359(5) Uani 1 1 d . . . . .
H11A H 0.8948 0.1426 0.5352 0.043 Uiso 1 1 calc R U . . .
H11B H 0.7339 0.1252 0.5542 0.043 Uiso 1 1 calc R U . . .
C12 C 0.7968(3) 0.2493(2) 0.62180(12) 0.0353(5) Uani 1 1 d . . . . .
H12A H 0.6943 0.3165 0.6294 0.042 Uiso 1 1 calc R U . . .
H12B H 0.8665 0.3068 0.6174 0.042 Uiso 1 1 calc R U . . .
C13 C 0.1344(3) -0.1076(3) -0.11232(13) 0.0460(6) Uani 1 1 d . . . . .
H13C H 0.1022 -0.0893 -0.1633 0.055 Uiso 1 1 calc R U . . .
C14 C 0.1798(3) -0.0032(3) -0.08550(13) 0.0458(7) Uani 1 1 d . . . . .
H14C H 0.1758 0.0859 -0.1179 0.055 Uiso 1 1 calc R U . . .
C15 C 0.2316(2) -0.0299(2) -0.01036(11) 0.0262(4) Uani 1 1 d . . . . .
C16 C 0.2285(3) -0.1617(3) 0.03508(12) 0.0449(6) Uani 1 1 d . . . . .
H16C H 0.2593 -0.1831 0.0864 0.054 Uiso 1 1 calc R U . . .
C17 C 0.1806(3) -0.2613(3) 0.00523(13) 0.0489(7) Uani 1 1 d . . . . .
H17C H 0.1797 -0.3498 0.0366 0.059 Uiso 1 1 calc R U . . .
C18 C 0.2920(2) 0.0760(2) 0.01952(11) 0.0257(4) Uani 1 1 d . . . . .
C19 C 0.3525(3) 0.0443(3) 0.09405(12) 0.0403(6) Uani 1 1 d . . . . .
H19C H 0.3507 -0.0420 0.1272 0.048 Uiso 1 1 calc R U . . .
C20 C 0.4146(3) 0.1398(3) 0.11863(13) 0.0425(6) Uani 1 1 d . . . . .
H20C H 0.4547 0.1180 0.1685 0.051 Uiso 1 1 calc R U . . .
C21 C 0.3609(3) 0.2985(2) 0.00115(12) 0.0335(5) Uani 1 1 d . . . . .
H21C H 0.3636 0.3863 -0.0303 0.040 Uiso 1 1 calc R U . . .
C22 C 0.2974(3) 0.2067(2) -0.02673(12) 0.0338(5) Uani 1 1 d . . . . .
H22C H 0.2579 0.2323 -0.0769 0.041 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 O2 1.5037(15) . ?
P1 O1 1.5154(15) . ?
P1 O3 1.5610(15) . ?
P1 C1 1.787(2) . ?
P2 O6 1.4908(15) . ?
P2 O5 1.5318(15) . ?
P2 O4 1.5554(16) . ?
P2 C6 1.776(2) . ?
P3 O7 1.5021(14) . ?
P3 O9 1.5185(15) . ?
P3 O8 1.5635(14) . ?
P3 C7 1.789(2) . ?
P4 O11 1.4815(15) . ?
P4 O10 1.5516(16) . ?
P4 O12 1.5596(15) . ?
P4 C12 1.786(2) . ?
O3 H3 0.8200 . ?
O4 H4 0.8200 . ?
O5 H5 0.8200 . ?
O8 H8 0.8200 . ?
O10 H10 0.8200 . ?
O12 H12 0.8200 . ?
N1 C13 1.320(3) . ?
N1 C17 1.320(3) . ?
N1 H1 0.8600 . ?
N2 C21 1.321(3) . ?
N2 C20 1.329(3) . ?
N2 H2 0.8600 . ?
C1 C2 1.515(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.519(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.505(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.512(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.521(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.525(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.525(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.523(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.521(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.529(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.370(3) . ?
C13 H13C 0.9300 . ?
C14 C15 1.383(3) . ?
C14 H14C 0.9300 . ?
C15 C16 1.380(3) . ?
C15 C18 1.489(3) . ?
C16 C17 1.369(3) . ?
C16 H16C 0.9300 . ?
C17 H17C 0.9300 . ?
C18 C22 1.385(3) . ?
C18 C19 1.392(3) . ?
C19 C20 1.368(3) . ?
C19 H19C 0.9300 . ?
C20 H20C 0.9300 . ?
C21 C22 1.373(3) . ?
C21 H21C 0.9300 . ?
C22 H22C 0.9300 . ?

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
O2 P1 O1 115.22(9) . . ?
O2 P1 O3 110.91(9) . . ?
O1 P1 O3 106.80(8) . . ?
O2 P1 C1 107.79(10) . . ?
O1 P1 C1 108.16(10) . . ?
O3 P1 C1 107.71(11) . . ?
O6 P2 O5 112.74(9) . . ?
O6 P2 O4 107.99(9) . . ?
O5 P2 O4 106.37(9) . . ?
O6 P2 C6 112.67(10) . . ?
O5 P2 C6 108.42(10) . . ?
O4 P2 C6 108.38(10) . . ?
O7 P3 O9 114.31(8) . . ?
O7 P3 O8 106.61(8) . . ?
O9 P3 O8 109.52(9) . . ?
O7 P3 C7 109.28(9) . . ?
O9 P3 C7 108.04(10) . . ?
O8 P3 C7 108.98(9) . . ?
O11 P4 O10 111.17(9) . . ?
O11 P4 O12 109.07(8) . . ?
O10 P4 O12 107.70(10) . . ?
O11 P4 C12 113.59(10) . . ?
O10 P4 C12 108.23(10) . . ?
O12 P4 C12 106.84(10) . . ?
P1 O3 H3 109.5 . . ?
P2 O4 H4 109.5 . . ?
P2 O5 H5 109.5 . . ?
P3 O8 H8 109.5 . . ?
P4 O10 H10 109.5 . . ?
P4 O12 H12 109.5 . . ?
C13 N1 C17 120.21(19) . . ?
C13 N1 H1 119.9 . . ?
C17 N1 H1 119.9 . . ?
C21 N2 C20 121.01(18) . . ?
C21 N2 H2 119.5 . . ?
C20 N2 H2 119.5 . . ?
C2 C1 P1 115.38(17) . . ?
C2 C1 H1A 108.4 . . ?
P1 C1 H1A 108.4 . . ?
C2 C1 H1B 108.4 . . ?
P1 C1 H1B 108.4 . . ?
H1A C1 H1B 107.5 . . ?
C1 C2 C3 113.1(2) . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 C2 113.5(2) . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C3 C4 C5 114.1(2) . . ?
C3 C4 H4A 108.7 . . ?
C5 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C5 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C4 C5 C6 111.92(19) . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C5 C6 P2 115.32(15) . . ?
C5 C6 H6A 108.4 . . ?
P2 C6 H6A 108.4 . . ?
C5 C6 H6B 108.4 . . ?
P2 C6 H6B 108.4 . . ?
H6A C6 H6B 107.5 . . ?
C8 C7 P3 115.49(15) . . ?
C8 C7 H7A 108.4 . . ?
P3 C7 H7A 108.4 . . ?
C8 C7 H7B 108.4 . . ?
P3 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
C7 C8 C9 113.00(18) . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C8 112.44(19) . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C9 114.10(19) . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C10 C11 C12 112.57(18) . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 P4 113.99(15) . . ?
C11 C12 H12A 108.8 . . ?
P4 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
P4 C12 H12B 108.8 . . ?
H12A C12 H12B 107.6 . . ?
N1 C13 C14 121.3(2) . . ?
N1 C13 H13C 119.4 . . ?
C14 C13 H13C 119.4 . . ?
C13 C14 C15 120.2(2) . . ?
C13 C14 H14C 119.9 . . ?
C15 C14 H14C 119.9 . . ?
C16 C15 C14 116.62(19) . . ?
C16 C15 C18 121.65(18) . . ?
C14 C15 C18 121.71(18) . . ?
C17 C16 C15 120.5(2) . . ?
C17 C16 H16C 119.7 . . ?
C15 C16 H16C 119.7 . . ?
N1 C17 C16 121.1(2) . . ?
N1 C17 H17C 119.5 . . ?
C16 C17 H17C 119.5 . . ?
C22 C18 C19 117.05(18) . . ?
C22 C18 C15 121.36(18) . . ?
C19 C18 C15 121.51(18) . . ?
C20 C19 C18 120.1(2) . . ?
C20 C19 H19C 120.0 . . ?
C18 C19 H19C 120.0 . . ?
N2 C20 C19 120.8(2) . . ?
N2 C20 H20C 119.6 . . ?
C19 C20 H20C 119.6 . . ?
N2 C21 C22 120.76(19) . . ?
N2 C21 H21C 119.6 . . ?
C22 C21 H21C 119.6 . . ?
C21 C22 C18 120.26(19) . . ?
C21 C22 H22C 119.9 . . ?
C18 C22 H22C 119.9 . . ?

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
O2 P1 C1 C2 50.7(2) . . . . ?
O1 P1 C1 C2 175.91(18) . . . . ?
O3 P1 C1 C2 -69.0(2) . . . . ?
P1 C1 C2 C3 -169.28(19) . . . . ?
C1 C2 C3 C4 179.0(2) . . . . ?
C2 C3 C4 C5 -171.1(2) . . . . ?
C3 C4 C5 C6 -173.7(2) . . . . ?
C4 C5 C6 P2 -166.49(18) . . . . ?
O6 P2 C6 C5 -160.95(17) . . . . ?
O5 P2 C6 C5 73.56(19) . . . . ?
O4 P2 C6 C5 -41.5(2) . . . . ?
O7 P3 C7 C8 175.52(15) . . . . ?
O9 P3 C7 C8 -59.55(18) . . . . ?
O8 P3 C7 C8 59.38(19) . . . . ?
P3 C7 C8 C9 177.94(16) . . . . ?
C7 C8 C9 C10 175.57(19) . . . . ?
C8 C9 C10 C11 177.46(19) . . . . ?
C9 C10 C11 C12 -178.6(2) . . . . ?
C10 C11 C12 P4 170.74(16) . . . . ?
O11 P4 C12 C11 61.8(2) . . . . ?
O10 P4 C12 C11 -174.19(17) . . . . ?
O12 P4 C12 C11 -58.46(19) . . . . ?
C17 N1 C13 C14 0.2(4) . . . . ?
N1 C13 C14 C15 1.5(4) . . . . ?
C13 C14 C15 C16 -2.5(4) . . . . ?
C13 C14 C15 C18 175.7(2) . . . . ?
C14 C15 C16 C17 1.9(4) . . . . ?
C18 C15 C16 C17 -176.3(2) . . . . ?
C13 N1 C17 C16 -0.8(4) . . . . ?
C15 C16 C17 N1 -0.3(4) . . . . ?
C16 C15 C18 C22 178.8(2) . . . . ?
C14 C15 C18 C22 0.6(3) . . . . ?
C16 C15 C18 C19 2.0(3) . . . . ?
C14 C15 C18 C19 -176.1(2) . . . . ?
C22 C18 C19 C20 -0.4(4) . . . . ?
C15 C18 C19 C20 176.5(2) . . . . ?
C21 N2 C20 C19 0.7(4) . . . . ?
C18 C19 C20 N2 -0.1(4) . . . . ?
C20 N2 C21 C22 -0.8(3) . . . . ?
N2 C21 C22 C18 0.3(3) . . . . ?
C19 C18 C22 C21 0.3(3) . . . . ?
C15 C18 C22 C21 -176.6(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O7 0.86 1.72 2.573(2) 175.1 .
O8 H8 O1 0.82 1.85 2.619(2) 156.4 .
N1 H1 O6 0.86 1.68 2.531(2) 169.5 1_444
O12 H12 O1 0.82 1.79 2.602(2) 171.2 2_666
O10 H10 O9 0.82 1.76 2.526(2) 154.4 2_666
O4 H4 O9 0.82 1.77 2.575(2) 168.2 2_666
O5 H5 O2 0.82 1.66 2.461(2) 165.6 2_766
O3 H3 O11 0.82 1.81 2.612(2) 163.8 2_766

_refine_diff_density_max         0.390
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.047

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_exp_668_100
_database_code_depnum_ccdc_archive 'CCDC 1433279'
_audit_update_record             
;
2015-10-25 deposited with the CCDC.
2016-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H28 N O6 P2'
_chemical_formula_weight         380.32

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'
N N 0.0061 0.0033 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   23.4234(7)
_cell_length_b                   4.64205(13)
_cell_length_c                   16.9643(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.720(3)
_cell_angle_gamma                90
_cell_volume                     1784.02(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    106(2)
_cell_measurement_reflns_used    5959
_cell_measurement_theta_min      2.8417
_cell_measurement_theta_max      28.9714

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_F_000             812
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.275
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83116
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      106(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Xcalibur-EOS
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20584
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_av_R_equivalents  0.0812
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.847
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3141
_reflns_number_gt                2396
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0431P)²+0.6777P] 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         3141
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.0974
_refine_ls_wR_factor_gt          0.0888
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.002
_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 0.64829(3) 0.29262(15) 0.33843(4) 0.01061(18) Uani 1 1 d . . . . .
P2 P 1.24991(3) 0.03457(15) 0.84923(4) 0.01090(18) Uani 1 1 d . . . . .
O6 O 1.23814(8) 0.2915(4) 0.90145(11) 0.0140(4) Uani 1 1 d . . . . .
H6 H 1.2527 0.4383 0.8880 0.021 Uiso 1 1 calc R U . . .
O3 O 0.63242(8) 0.0409(4) 0.39065(10) 0.0143(4) Uani 1 1 d . . . . .
H3 H 0.6238 -0.1032 0.3621 0.021 Uiso 1 1 calc R U . . .
O1 O 0.64826(7) 0.1802(4) 0.25377(10) 0.0121(4) Uani 1 1 d . . . . .
O2 O 0.60533(7) 0.5371(4) 0.33513(11) 0.0131(4) Uani 1 1 d . . . . .
O4 O 1.28267(7) -0.2077(4) 0.89887(11) 0.0144(4) Uani 1 1 d . . . . .
O5 O 1.28210(8) 0.1643(4) 0.78807(11) 0.0147(4) Uani 1 1 d . . . . .
H5 H 1.3043 0.0432 0.7769 0.022 Uiso 1 1 calc R U . . .
C3 C 0.82682(11) 0.3249(6) 0.46328(16) 0.0151(6) Uani 1 1 d . . . . .
H3A H 0.8423 0.4329 0.4243 0.018 Uiso 1 1 calc R U . . .
H3B H 0.8195 0.4607 0.5031 0.018 Uiso 1 1 calc R U . . .
N1 N 0.59135(9) 0.5275(5) 0.13511(13) 0.0150(5) Uani 1 1 d . . . . .
H1 H 0.6140 0.4123 0.1687 0.018 Uiso 1 1 calc R U . . .
C1 C 0.72042(11) 0.4152(6) 0.39127(16) 0.0139(6) Uani 1 1 d . . . . .
H1A H 0.7337 0.5507 0.3562 0.017 Uiso 1 1 calc R U . . .
H1B H 0.7168 0.5207 0.4391 0.017 Uiso 1 1 calc R U . . .
C10 C 1.17879(11) -0.0933(6) 0.79390(16) 0.0150(6) Uani 1 1 d . . . . .
H10A H 1.1848 -0.2440 0.7572 0.018 Uiso 1 1 calc R U . . .
H10B H 1.1599 -0.1813 0.8326 0.018 Uiso 1 1 calc R U . . .
C5 C 0.93039(11) 0.2579(6) 0.55373(17) 0.0169(6) Uani 1 1 d . . . . .
H5A H 0.9476 0.3595 0.5154 0.020 Uiso 1 1 calc R U . . .
H5B H 0.9208 0.3996 0.5903 0.020 Uiso 1 1 calc R U . . .
C7 C 1.03304(11) 0.1953(6) 0.64924(17) 0.0170(6) Uani 1 1 d . . . . .
H7A H 1.0238 0.3381 0.6859 0.020 Uiso 1 1 calc R U . . .
H7B H 1.0502 0.2954 0.6106 0.020 Uiso 1 1 calc R U . . .
C2 C 0.76836(11) 0.1891(6) 0.41859(16) 0.0140(6) Uani 1 1 d . . . . .
H2A H 0.7736 0.0850 0.3714 0.017 Uiso 1 1 calc R U . . .
H2B H 0.7562 0.0521 0.4543 0.017 Uiso 1 1 calc R U . . .
C6 C 0.97625(11) 0.0505(6) 0.60324(17) 0.0166(6) Uani 1 1 d . . . . .
H6A H 0.9592 -0.0495 0.6420 0.020 Uiso 1 1 calc R U . . .
H6B H 0.9856 -0.0926 0.5667 0.020 Uiso 1 1 calc R U . . .
C9 C 1.13593(11) 0.1265(6) 0.74399(17) 0.0155(6) Uani 1 1 d . . . . .
H9A H 1.1276 0.2739 0.7800 0.019 Uiso 1 1 calc R U . . .
H9B H 1.1542 0.2191 0.7053 0.019 Uiso 1 1 calc R U . . .
C13 C 0.51950(11) 0.8984(5) 0.02894(16) 0.0112(6) Uani 1 1 d . . . . .
C8 C 1.07855(11) -0.0145(6) 0.69839(17) 0.0171(6) Uani 1 1 d . . . . .
H8A H 1.0615 -0.1129 0.7374 0.021 Uiso 1 1 calc R U . . .
H8B H 1.0873 -0.1586 0.6617 0.021 Uiso 1 1 calc R U . . .
C4 C 0.87349(11) 0.1120(6) 0.50665(16) 0.0147(6) Uani 1 1 d . . . . .
H4A H 0.8825 -0.0183 0.4668 0.018 Uiso 1 1 calc R U . . .
H4B H 0.8577 -0.0018 0.5442 0.018 Uiso 1 1 calc R U . . .
C11 C 0.60317(12) 0.5838(6) 0.06406(17) 0.0168(6) Uani 1 1 d . . . . .
H11 H 0.6351 0.4953 0.0507 0.020 Uiso 1 1 calc R U . . .
C15 C 0.54524(12) 0.6449(6) 0.15550(17) 0.0199(7) Uani 1 1 d . . . . .
H15 H 0.5380 0.6007 0.2056 0.024 Uiso 1 1 calc R U . . .
C14 C 0.50833(12) 0.8299(6) 0.10367(16) 0.0176(6) Uani 1 1 d . . . . .
H14 H 0.4760 0.9095 0.1182 0.021 Uiso 1 1 calc R U . . .
C12 C 0.56845(11) 0.7719(6) 0.01039(16) 0.0158(6) Uani 1 1 d . . . . .
H12 H 0.5776 0.8153 -0.0385 0.019 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 O2 1.5084(18) . ?
P1 O1 1.5279(18) . ?
P1 O3 1.5671(18) . ?
P1 C1 1.792(3) . ?
P2 O4 1.4948(18) . ?
P2 O5 1.5509(18) . ?
P2 O6 1.5514(18) . ?
P2 C10 1.793(3) . ?
C3 C4 1.518(4) . ?
C3 C2 1.523(3) . ?
N1 C11 1.330(3) . ?
N1 C15 1.332(3) . ?
C1 C2 1.521(4) . ?
C10 C9 1.528(4) . ?
C5 C6 1.526(4) . ?
C5 C4 1.527(4) . ?
C7 C6 1.518(4) . ?
C7 C8 1.526(4) . ?
C9 C8 1.518(4) . ?
C13 C12 1.393(4) . ?
C13 C14 1.395(4) . ?
C13 C13 1.494(5) 3_675 ?
C11 C12 1.370(4) . ?
C15 C14 1.368(4) . ?

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
O2 P1 O1 112.40(10) . . ?
O2 P1 O3 109.29(10) . . ?
O1 P1 O3 109.47(10) . . ?
O2 P1 C1 108.35(12) . . ?
O1 P1 C1 110.71(11) . . ?
O3 P1 C1 106.43(12) . . ?
O4 P2 O5 113.69(10) . . ?
O4 P2 O6 113.39(11) . . ?
O5 P2 O6 105.71(10) . . ?
O4 P2 C10 108.75(12) . . ?
O5 P2 C10 108.86(12) . . ?
O6 P2 C10 106.09(12) . . ?
C4 C3 C2 114.7(2) . . ?
C11 N1 C15 121.6(2) . . ?
C2 C1 P1 117.55(19) . . ?
C9 C10 P2 117.47(19) . . ?
C6 C5 C4 114.0(2) . . ?
C6 C7 C8 113.4(2) . . ?
C1 C2 C3 111.5(2) . . ?
C7 C6 C5 114.0(2) . . ?
C8 C9 C10 111.5(2) . . ?
C12 C13 C14 117.7(2) . . ?
C12 C13 C13 121.2(3) . 3_675 ?
C14 C13 C13 121.1(3) . 3_675 ?
C9 C8 C7 114.1(2) . . ?
C3 C4 C5 113.0(2) . . ?
N1 C11 C12 120.2(3) . . ?
N1 C15 C14 120.8(3) . . ?
C15 C14 C13 119.6(3) . . ?
C11 C12 C13 120.1(3) . . ?

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
O2 P1 C1 C2 166.69(19) . . . . ?
O1 P1 C1 C2 -69.6(2) . . . . ?
O3 P1 C1 C2 49.3(2) . . . . ?
O4 P2 C10 C9 175.39(19) . . . . ?
O5 P2 C10 C9 -60.2(2) . . . . ?
O6 P2 C10 C9 53.1(2) . . . . ?
P1 C1 C2 C3 -179.38(19) . . . . ?
C4 C3 C2 C1 168.7(2) . . . . ?
C8 C7 C6 C5 -179.9(2) . . . . ?
C4 C5 C6 C7 179.3(2) . . . . ?
P2 C10 C9 C8 178.07(19) . . . . ?
C10 C9 C8 C7 178.3(2) . . . . ?
C6 C7 C8 C9 179.3(2) . . . . ?
C2 C3 C4 C5 -177.5(2) . . . . ?
C6 C5 C4 C3 175.5(2) . . . . ?
C15 N1 C11 C12 1.6(4) . . . . ?
C11 N1 C15 C14 -0.3(4) . . . . ?
N1 C15 C14 C13 -0.6(4) . . . . ?
C12 C13 C14 C15 0.2(4) . . . . ?
C13 C13 C14 C15 -179.4(3) 3_675 . . . ?
N1 C11 C12 C13 -2.0(4) . . . . ?
C14 C13 C12 C11 1.1(4) . . . . ?
C13 C13 C12 C11 -179.3(3) 3_675 . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.86 1.82 2.658(3) 165.8 .
O3 H3 O2 0.82 1.76 2.540(3) 159.5 1_545
O6 H6 O4 0.82 1.78 2.553(2) 157.0 1_565
O5 H5 O1 0.82 1.70 2.512(2) 173.6 3_756

_refine_diff_density_max         0.388
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.063

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_exp_642_120
_database_code_depnum_ccdc_archive 'CCDC 1433280'
_audit_update_record             
;
2015-10-25 deposited with the CCDC.
2016-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H30 N O6 P2'
_chemical_formula_weight         394.35

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   4.75510(10)
_cell_length_b                   8.7442(3)
_cell_length_c                   22.6864(8)
_cell_angle_alpha                81.639(3)
_cell_angle_beta                 87.130(3)
_cell_angle_gamma                88.196(3)
_cell_volume                     931.81(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    122(2)
_cell_measurement_reflns_used    5019
_cell_measurement_theta_min      3.1691
_cell_measurement_theta_max      30.1507

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_F_000             422
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.266
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96038
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      122(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Xcalibur-EOS
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7612
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.175
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3257
_reflns_number_gt                2780
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0443P)²+0.6143P] 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         3257
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0967
_refine_ls_wR_factor_gt          0.0909
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 -0.58166(10) 0.96336(6) 0.14034(2) 0.01231(15) Uani 1 1 d . . . . .
P2 P 0.87740(10) 0.63391(6) 0.75881(2) 0.01282(15) Uani 1 1 d . . . . .
O4 O 1.1390(3) 0.54798(18) 0.77915(7) 0.0204(4) Uani 1 1 d . . . . .
O2 O -0.8493(3) 1.04473(18) 0.16062(7) 0.0171(3) Uani 1 1 d . . . . .
O1 O -0.6196(3) 0.88358(18) 0.08686(7) 0.0193(4) Uani 1 1 d . . . . .
O5 O 0.9031(3) 0.81135(17) 0.75026(7) 0.0193(4) Uani 1 1 d . . . . .
H5 H 0.8804 0.8422 0.7827 0.029 Uiso 1 1 calc R U . . .
O3 O -0.3525(3) 1.09077(18) 0.12420(7) 0.0194(4) Uani 1 1 d . . . . .
H3 H -0.2012 1.0572 0.1371 0.029 Uiso 1 1 calc R U . . .
O6 O 0.6335(3) 0.5842(2) 0.80481(7) 0.0217(4) Uani 1 1 d . . . . .
H6 H 0.4835 0.5943 0.7882 0.033 Uiso 1 1 calc R U . . .
C9 C 0.5239(4) 0.6576(3) 0.59279(9) 0.0156(5) Uani 1 1 d . . . . .
H9A H 0.6980 0.6397 0.5704 0.019 Uiso 1 1 calc R U . . .
H9B H 0.4290 0.5598 0.6017 0.019 Uiso 1 1 calc R U . . .
C3 C -0.2289(4) 0.7929(3) 0.30139(9) 0.0148(5) Uani 1 1 d . . . . .
H3A H -0.0512 0.7712 0.2810 0.018 Uiso 1 1 calc R U . . .
H3B H -0.3226 0.6954 0.3131 0.018 Uiso 1 1 calc R U . . .
C5 C 0.0149(4) 0.7562(3) 0.39954(9) 0.0151(5) Uani 1 1 d . . . . .
H5A H 0.1900 0.7344 0.3782 0.018 Uiso 1 1 calc R U . . .
H5B H -0.0795 0.6589 0.4111 0.018 Uiso 1 1 calc R U . . .
C1 C -0.4497(4) 0.8290(3) 0.20074(9) 0.0153(5) Uani 1 1 d . . . . .
H1A H -0.5786 0.7440 0.2096 0.018 Uiso 1 1 calc R U . . .
H1B H -0.2699 0.7868 0.1877 0.018 Uiso 1 1 calc R U . . .
C6 C 0.0836(4) 0.8211(2) 0.45578(9) 0.0145(5) Uani 1 1 d . . . . .
H6A H 0.1794 0.9180 0.4445 0.017 Uiso 1 1 calc R U . . .
H6B H -0.0907 0.8426 0.4775 0.017 Uiso 1 1 calc R U . . .
C2 C -0.4102(4) 0.8973(2) 0.25832(9) 0.0136(4) Uani 1 1 d . . . . .
H2A H -0.3230 0.9971 0.2484 0.016 Uiso 1 1 calc R U . . .
H2B H -0.5932 0.9134 0.2776 0.016 Uiso 1 1 calc R U . . .
C7 C 0.2679(4) 0.7115(3) 0.49658(9) 0.0148(5) Uani 1 1 d . . . . .
H7A H 0.4422 0.6908 0.4747 0.018 Uiso 1 1 calc R U . . .
H7B H 0.1726 0.6141 0.5071 0.018 Uiso 1 1 calc R U . . .
C4 C -0.1694(4) 0.8619(3) 0.35744(9) 0.0152(5) Uani 1 1 d . . . . .
H4A H -0.0769 0.9597 0.3459 0.018 Uiso 1 1 calc R U . . .
H4B H -0.3466 0.8823 0.3783 0.018 Uiso 1 1 calc R U . . .
C11 C 0.7921(4) 0.5935(3) 0.68671(9) 0.0141(4) Uani 1 1 d . . . . .
H11A H 0.9665 0.5861 0.6631 0.017 Uiso 1 1 calc R U . . .
H11B H 0.7064 0.4930 0.6917 0.017 Uiso 1 1 calc R U . . .
C10 C 0.5958(4) 0.7099(3) 0.65131(9) 0.0143(5) Uani 1 1 d . . . . .
H10A H 0.4236 0.7226 0.6751 0.017 Uiso 1 1 calc R U . . .
H10B H 0.6853 0.8094 0.6430 0.017 Uiso 1 1 calc R U . . .
C8 C 0.3394(4) 0.7709(3) 0.55380(9) 0.0154(5) Uani 1 1 d . . . . .
H8A H 0.4357 0.8680 0.5437 0.018 Uiso 1 1 calc R U . . .
H8B H 0.1661 0.7907 0.5762 0.018 Uiso 1 1 calc R U . . .
N1 N 0.9935(4) 0.7329(2) 0.05125(8) 0.0174(4) Uani 1 1 d . . . . .
H1 H 1.1177 0.7889 0.0635 0.021 Uiso 1 1 calc R U . . .
C16 C 0.9042(5) 0.6061(3) 0.08615(10) 0.0227(5) Uani 1 1 d . . . . .
H16C H 0.9755 0.5799 0.1238 0.027 Uiso 1 1 calc R U . . .
C14 C 0.6042(4) 0.5508(2) 0.01120(10) 0.0157(5) Uani 1 1 d . . . . .
C15 C 0.7095(5) 0.5137(3) 0.06755(10) 0.0221(5) Uani 1 1 d . . . . .
H15C H 0.6480 0.4263 0.0926 0.026 Uiso 1 1 calc R U . . .
C13 C 0.6983(5) 0.6842(3) -0.02362(11) 0.0250(5) Uani 1 1 d . . . . .
H13C H 0.6305 0.7136 -0.0614 0.030 Uiso 1 1 calc R U . . .
C12 C 0.8910(5) 0.7729(3) -0.00239(11) 0.0256(5) Uani 1 1 d . . . . .
H12C H 0.9515 0.8629 -0.0260 0.031 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 1.5058(15) . ?
P1 O2 1.5222(15) . ?
P1 O3 1.5750(15) . ?
P1 C1 1.795(2) . ?
P2 O4 1.4910(15) . ?
P2 O5 1.5434(16) . ?
P2 O6 1.5495(16) . ?
P2 C11 1.791(2) . ?
C9 C8 1.517(3) . ?
C9 C10 1.523(3) . ?
C3 C2 1.519(3) . ?
C3 C4 1.527(3) . ?
C5 C4 1.520(3) . ?
C5 C6 1.523(3) . ?
C1 C2 1.535(3) . ?
C6 C7 1.521(3) . ?
C7 C8 1.524(3) . ?
C11 C10 1.526(3) . ?
N1 C12 1.329(3) . ?
N1 C16 1.333(3) . ?
C16 C15 1.369(3) . ?
C14 C13 1.384(3) . ?
C14 C15 1.387(3) . ?
C14 C14 1.505(4) 2_665 ?
C13 C12 1.367(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 O2 113.12(8) . . ?
O1 P1 O3 109.26(9) . . ?
O2 P1 O3 106.92(9) . . ?
O1 P1 C1 110.47(9) . . ?
O2 P1 C1 110.40(10) . . ?
O3 P1 C1 106.38(9) . . ?
O4 P2 O5 113.82(9) . . ?
O4 P2 O6 108.41(9) . . ?
O5 P2 O6 109.83(9) . . ?
O4 P2 C11 110.94(9) . . ?
O5 P2 C11 103.95(9) . . ?
O6 P2 C11 109.83(9) . . ?
C8 C9 C10 114.66(18) . . ?
C2 C3 C4 113.62(17) . . ?
C4 C5 C6 114.65(18) . . ?
C2 C1 P1 114.90(15) . . ?
C7 C6 C5 112.82(17) . . ?
C3 C2 C1 112.18(17) . . ?
C6 C7 C8 114.66(18) . . ?
C5 C4 C3 112.70(18) . . ?
C10 C11 P2 116.56(14) . . ?
C9 C10 C11 111.59(17) . . ?
C9 C8 C7 112.57(17) . . ?
C12 N1 C16 120.12(19) . . ?
N1 C16 C15 121.2(2) . . ?
C13 C14 C15 117.5(2) . . ?
C13 C14 C14 121.4(2) . 2_665 ?
C15 C14 C14 121.1(3) . 2_665 ?
C16 C15 C14 119.9(2) . . ?
C12 C13 C14 120.0(2) . . ?
N1 C12 C13 121.3(2) . . ?

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
O1 P1 C1 C2 -178.49(14) . . . . ?
O2 P1 C1 C2 -52.61(17) . . . . ?
O3 P1 C1 C2 63.04(17) . . . . ?
C4 C5 C6 C7 179.93(18) . . . . ?
C4 C3 C2 C1 176.28(17) . . . . ?
P1 C1 C2 C3 -164.80(14) . . . . ?
C5 C6 C7 C8 -179.33(17) . . . . ?
C6 C5 C4 C3 179.16(17) . . . . ?
C2 C3 C4 C5 -179.38(17) . . . . ?
O4 P2 C11 C10 -160.02(15) . . . . ?
O5 P2 C11 C10 -37.30(18) . . . . ?
O6 P2 C11 C10 80.16(18) . . . . ?
C8 C9 C10 C11 -177.48(17) . . . . ?
P2 C11 C10 C9 -176.25(15) . . . . ?
C10 C9 C8 C7 -178.61(17) . . . . ?
C6 C7 C8 C9 -179.84(18) . . . . ?
C12 N1 C16 C15 0.9(3) . . . . ?
N1 C16 C15 C14 0.7(4) . . . . ?
C13 C14 C15 C16 -1.5(3) . . . . ?
C14 C14 C15 C16 178.3(2) 2_665 . . . ?
C15 C14 C13 C12 0.9(3) . . . . ?
C14 C14 C13 C12 -179.0(2) 2_665 . . . ?
C16 N1 C12 C13 -1.6(4) . . . . ?
C14 C13 C12 N1 0.7(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.86 1.67 2.527(2) 174.6 1_755
O5 H5 O2 0.82 1.73 2.531(2) 164.4 2_576
O6 H6 O4 0.82 1.73 2.4911(19) 153.8 1_455
O3 H3 O2 0.82 1.78 2.5711(19) 162.6 1_655

_refine_diff_density_max         0.425
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.062

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_exp_643_100_a
_database_code_depnum_ccdc_archive 'CCDC 1433281'
_audit_update_record             
;
2015-10-25 deposited with the CCDC.
2016-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H64 N2 O12 P4'
_chemical_formula_weight         816.75

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.1869(18)
_cell_length_b                   9.2725(19)
_cell_length_c                   24.348(5)
_cell_angle_alpha                83.68(3)
_cell_angle_beta                 81.01(3)
_cell_angle_gamma                81.40(3)
_cell_volume                     2017.6(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    8610
_cell_measurement_theta_min      2.9168
_cell_measurement_theta_max      29.9731

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             876
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.248
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Xcalibur-EOS
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21099
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.923
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7072
_reflns_number_gt                5623
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0580P)²+8.9258P] 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         7072
_refine_ls_number_parameters     476
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0717
_refine_ls_wR_factor_ref         0.1933
_refine_ls_wR_factor_gt          0.1843
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_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 0.47622(11) 1.05206(11) 0.17030(5) 0.0119(3) Uani 1 1 d . . . . .
P4 P 0.01992(11) -0.29212(11) 0.82088(5) 0.0119(3) Uani 1 1 d . . . . .
P2 P 0.04584(11) 0.20478(11) 0.82308(5) 0.0122(3) Uani 1 1 d . . . . .
O11 O 0.1181(3) -0.3754(3) 0.86329(12) 0.0154(6) Uani 1 1 d . . . . .
H11 H 0.1871 -0.4282 0.8469 0.023 Uiso 1 1 calc R U . . .
O10 O -0.0763(3) -0.1612(3) 0.84507(12) 0.0166(7) Uani 1 1 d . . . . .
O5 O 0.1421(3) 0.1108(3) 0.86442(13) 0.0193(7) Uani 1 1 d . . . . .
H5 H 0.2302 0.1073 0.8513 0.029 Uiso 1 1 calc R U . . .
O6 O -0.0732(3) 0.1100(3) 0.81382(14) 0.0196(7) Uani 1 1 d . . . . .
H6 H -0.0459 0.0237 0.8231 0.029 Uiso 1 1 calc R U . . .
O12 O -0.0793(3) -0.3965(3) 0.80431(13) 0.0184(7) Uani 1 1 d . . . . .
H12 H -0.0606 -0.4782 0.8203 0.028 Uiso 1 1 calc R U . . .
O4 O -0.0300(3) 0.3449(3) 0.84490(13) 0.0187(7) Uani 1 1 d . . . . .
O9 O 0.5021(3) 0.4184(3) 0.13928(13) 0.0197(7) Uani 1 1 d . . . . .
H9 H 0.5368 0.3415 0.1553 0.030 Uiso 1 1 calc R U . . .
O7 O 0.6725(3) 0.5466(3) 0.18360(13) 0.0201(7) Uani 1 1 d . . . . .
O2 O 0.5659(3) 1.1685(3) 0.17915(13) 0.0207(7) Uani 1 1 d . . . . .
O8 O 0.4602(3) 0.6844(3) 0.13512(14) 0.0210(7) Uani 1 1 d . . . . .
H8 H 0.4979 0.7541 0.1418 0.031 Uiso 1 1 calc R U . . .
O1 O 0.5699(3) 0.9149(3) 0.15011(13) 0.0199(7) Uani 1 1 d . . . . .
O3 O 0.3708(3) 1.1137(4) 0.12472(13) 0.0222(7) Uani 1 1 d . . . . .
H3 H 0.2854 1.1339 0.1402 0.033 Uiso 1 1 calc R U . . .
P3 P 0.51554(12) 0.54595(12) 0.17183(5) 0.0141(3) Uani 1 1 d . . . . .
N1 N 0.3630(4) 0.8114(4) -0.00464(16) 0.0189(8) Uani 1 1 d . . . . .
H1 H 0.4526 0.7672 -0.0063 0.028 Uiso 0.5 1 calc R U P . .
N2 N 0.6392(4) 0.6811(4) -0.00490(16) 0.0185(8) Uani 1 1 d . . . . .
H2 H 0.5499 0.7244 -0.0056 0.028 Uiso 0.5 1 calc R U P . .
C33 C 0.1327(4) 0.8589(5) -0.04026(18) 0.0138(9) Uani 1 1 d . . . . .
H33C H 0.0746 0.8409 -0.0661 0.017 Uiso 1 1 calc R U . . .
C27 C 0.0757(4) 0.9591(4) -0.00081(17) 0.0122(8) Uani 1 1 d . . . . .
C28 C 0.9241(4) 0.5388(4) -0.00099(17) 0.0116(8) Uani 1 1 d . . . . .
C32 C 0.8595(4) 0.6416(5) 0.03647(18) 0.0161(9) Uani 1 1 d . . . . .
H32C H 0.9119 0.6632 0.0636 0.019 Uiso 1 1 calc R U . . .
C12 C 0.1623(5) 0.2350(5) 0.75815(18) 0.0175(9) Uani 1 1 d . . . . .
H12A H 0.2448 0.2819 0.7648 0.021 Uiso 1 1 calc R U . . .
H12B H 0.2033 0.1407 0.7446 0.021 Uiso 1 1 calc R U . . .
C24 C 0.1424(5) -0.2389(5) 0.75959(18) 0.0176(9) Uani 1 1 d . . . . .
H24A H 0.2098 -0.1795 0.7704 0.021 Uiso 1 1 calc R U . . .
H24B H 0.2019 -0.3266 0.7460 0.021 Uiso 1 1 calc R U . . .
C23 C 0.0694(5) -0.1539(5) 0.71137(18) 0.0173(9) Uani 1 1 d . . . . .
H23A H 0.0133 -0.0631 0.7237 0.021 Uiso 1 1 calc R U . . .
H23B H 0.0005 -0.2111 0.7002 0.021 Uiso 1 1 calc R U . . .
C11 C 0.0856(5) 0.3288(5) 0.71234(18) 0.0176(9) Uani 1 1 d . . . . .
H11A H 0.0125 0.2765 0.7014 0.021 Uiso 1 1 calc R U . . .
H11B H 0.0340 0.4190 0.7268 0.021 Uiso 1 1 calc R U . . .
C34 C 0.2755(5) 0.7869(5) -0.04074(18) 0.0168(9) Uani 1 1 d . . . . .
H34C H 0.3119 0.7195 -0.0668 0.020 Uiso 1 1 calc R U . . .
C1 C 0.3526(5) 1.0090(5) 0.23270(18) 0.0196(10) Uani 1 1 d . . . . .
H1A H 0.2950 1.0994 0.2447 0.023 Uiso 1 1 calc R U . . .
H1B H 0.2836 0.9486 0.2237 0.023 Uiso 1 1 calc R U . . .
C17 C 0.2480(5) 0.2591(5) 0.42419(19) 0.0204(10) Uani 1 1 d . . . . .
H17A H 0.2036 0.3502 0.4397 0.024 Uiso 1 1 calc R U . . .
H17B H 0.1707 0.2192 0.4101 0.024 Uiso 1 1 calc R U . . .
C5 C 0.2537(5) 0.7546(5) 0.42641(18) 0.0191(10) Uani 1 1 d . . . . .
H5A H 0.2040 0.8441 0.4419 0.023 Uiso 1 1 calc R U . . .
H5B H 0.1802 0.7106 0.4117 0.023 Uiso 1 1 calc R U . . .
C20 C 0.2428(5) 0.0124(5) 0.56528(18) 0.0194(10) Uani 1 1 d . . . . .
H20A H 0.2896 -0.0784 0.5501 0.023 Uiso 1 1 calc R U . . .
H20B H 0.3186 0.0549 0.5793 0.023 Uiso 1 1 calc R U . . .
C30 C 0.6981(5) 0.5842(5) -0.04188(19) 0.0210(10) Uani 1 1 d . . . . .
H30C H 0.6427 0.5658 -0.0686 0.025 Uiso 1 1 calc R U . . .
C31 C 0.7174(5) 0.7108(5) 0.03288(19) 0.0185(10) Uani 1 1 d . . . . .
H31C H 0.6751 0.7802 0.0576 0.022 Uiso 1 1 calc R U . . .
C25 C 0.3105(5) 0.9045(5) 0.0338(2) 0.0228(10) Uani 1 1 d . . . . .
H25C H 0.3713 0.9191 0.0593 0.027 Uiso 1 1 calc R U . . .
C21 C 0.1229(5) -0.0219(5) 0.61378(18) 0.0194(10) Uani 1 1 d . . . . .
H21A H 0.0723 0.0691 0.6278 0.023 Uiso 1 1 calc R U . . .
H21B H 0.0502 -0.0699 0.6004 0.023 Uiso 1 1 calc R U . . .
C8 C 0.2508(5) 0.5068(5) 0.56695(18) 0.0195(10) Uani 1 1 d . . . . .
H8A H 0.3256 0.5500 0.5813 0.023 Uiso 1 1 calc R U . . .
H8B H 0.2993 0.4173 0.5512 0.023 Uiso 1 1 calc R U . . .
C3 C 0.3110(5) 0.8913(5) 0.33096(18) 0.0184(10) Uani 1 1 d . . . . .
H3A H 0.2591 0.9813 0.3455 0.022 Uiso 1 1 calc R U . . .
H3B H 0.2384 0.8426 0.3177 0.022 Uiso 1 1 calc R U . . .
C2 C 0.4268(4) 0.9300(5) 0.28158(18) 0.0158(9) Uani 1 1 d . . . . .
H2A H 0.4883 0.8412 0.2699 0.019 Uiso 1 1 calc R U . . .
H2B H 0.4906 0.9922 0.2929 0.019 Uiso 1 1 calc R U . . .
C29 C 0.8405(5) 0.5110(5) -0.04083(19) 0.0174(9) Uani 1 1 d . . . . .
H29C H 0.8803 0.4436 -0.0666 0.021 Uiso 1 1 calc R U . . .
C9 C 0.1321(5) 0.4680(5) 0.61565(18) 0.0194(10) Uani 1 1 d . . . . .
H9A H 0.0820 0.5572 0.6313 0.023 Uiso 1 1 calc R U . . .
H9B H 0.0586 0.4219 0.6019 0.023 Uiso 1 1 calc R U . . .
C7 C 0.1912(5) 0.6122(5) 0.52062(19) 0.0205(10) Uani 1 1 d . . . . .
H7A H 0.1419 0.7017 0.5362 0.025 Uiso 1 1 calc R U . . .
H7B H 0.1176 0.5688 0.5057 0.025 Uiso 1 1 calc R U . . .
C13 C 0.3877(5) 0.5390(5) 0.23527(19) 0.0219(10) Uani 1 1 d . . . . .
H13A H 0.3733 0.6338 0.2501 0.026 Uiso 1 1 calc R U . . .
H13B H 0.2925 0.5217 0.2267 0.026 Uiso 1 1 calc R U . . .
C10 C 0.1984(5) 0.3651(5) 0.66137(19) 0.0192(10) Uani 1 1 d . . . . .
H10A H 0.2759 0.4094 0.6734 0.023 Uiso 1 1 calc R U . . .
H10B H 0.2445 0.2746 0.6458 0.023 Uiso 1 1 calc R U . . .
C15 C 0.3150(5) 0.4002(5) 0.32941(19) 0.0208(10) Uani 1 1 d . . . . .
H15A H 0.2782 0.4936 0.3444 0.025 Uiso 1 1 calc R U . . .
H15B H 0.2328 0.3657 0.3165 0.025 Uiso 1 1 calc R U . . .
C4 C 0.3738(5) 0.7936(5) 0.37831(18) 0.0197(10) Uani 1 1 d . . . . .
H4A H 0.4444 0.8430 0.3924 0.024 Uiso 1 1 calc R U . . .
H4B H 0.4272 0.7041 0.3639 0.024 Uiso 1 1 calc R U . . .
C22 C 0.1858(5) -0.1195(5) 0.66128(18) 0.0200(10) Uani 1 1 d . . . . .
H22A H 0.2604 -0.0721 0.6738 0.024 Uiso 1 1 calc R U . . .
H22B H 0.2349 -0.2109 0.6472 0.024 Uiso 1 1 calc R U . . .
C26 C 0.1681(5) 0.9804(5) 0.03718(19) 0.0214(10) Uani 1 1 d . . . . .
H26C H 0.1342 1.0450 0.0645 0.026 Uiso 1 1 calc R U . . .
C14 C 0.4362(5) 0.4222(5) 0.28017(19) 0.0191(10) Uani 1 1 d . . . . .
H14A H 0.5213 0.4491 0.2937 0.023 Uiso 1 1 calc R U . . .
H14B H 0.4676 0.3300 0.2636 0.023 Uiso 1 1 calc R U . . .
C19 C 0.1838(5) 0.1173(5) 0.51857(19) 0.0211(10) Uani 1 1 d . . . . .
H19A H 0.1362 0.2078 0.5338 0.025 Uiso 1 1 calc R U . . .
H19B H 0.1089 0.0744 0.5042 0.025 Uiso 1 1 calc R U . . .
C18 C 0.3052(5) 0.1524(5) 0.47037(19) 0.0209(10) Uani 1 1 d . . . . .
H18A H 0.3811 0.1932 0.4849 0.025 Uiso 1 1 calc R U . . .
H18B H 0.3514 0.0620 0.4547 0.025 Uiso 1 1 calc R U . . .
C16 C 0.3693(5) 0.2915(5) 0.37551(19) 0.0216(10) Uani 1 1 d . . . . .
H16A H 0.4475 0.3293 0.3898 0.026 Uiso 1 1 calc R U . . .
H16B H 0.4123 0.2004 0.3597 0.026 Uiso 1 1 calc R U . . .
C6 C 0.3125(5) 0.6500(5) 0.47315(19) 0.0217(10) Uani 1 1 d . . . . .
H6A H 0.3857 0.6939 0.4881 0.026 Uiso 1 1 calc R U . . .
H6B H 0.3622 0.5604 0.4578 0.026 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 O2 1.504(3) . ?
P1 O1 1.509(3) . ?
P1 O3 1.589(3) . ?
P1 C1 1.794(4) . ?
P4 O10 1.508(3) . ?
P4 O11 1.544(3) . ?
P4 O12 1.548(3) . ?
P4 C24 1.793(4) . ?
P2 O4 1.491(3) . ?
P2 O5 1.552(3) . ?
P2 O6 1.558(3) . ?
P2 C12 1.785(4) . ?
O11 H11 0.8200 . ?
O5 H5 0.8200 . ?
O6 H6 0.8200 . ?
O12 H12 0.8200 . ?
O9 P3 1.524(3) . ?
O9 H9 0.8200 . ?
O7 P3 1.514(3) . ?
O8 P3 1.549(3) . ?
O8 H8 0.8200 . ?
O3 H3 0.8200 . ?
P3 C13 1.790(5) . ?
N1 C25 1.329(6) . ?
N1 C34 1.338(6) . ?
N1 H1 0.8600 . ?
N2 C31 1.327(6) . ?
N2 C30 1.338(6) . ?
N2 H2 0.8600 . ?
C33 C34 1.379(6) . ?
C33 C27 1.398(6) . ?
C33 H33C 0.9300 . ?
C27 C26 1.396(6) . ?
C27 C27 1.479(8) 2_575 ?
C28 C29 1.394(6) . ?
C28 C32 1.395(6) . ?
C28 C28 1.477(8) 2_765 ?
C32 C31 1.377(6) . ?
C32 H32C 0.9300 . ?
C12 C11 1.532(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C24 C23 1.528(6) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C23 C22 1.530(6) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C11 C10 1.529(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C34 H34C 0.9300 . ?
C1 C2 1.526(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C17 C18 1.518(6) . ?
C17 C16 1.532(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C5 C6 1.523(6) . ?
C5 C4 1.530(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C20 C21 1.524(6) . ?
C20 C19 1.525(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C30 C29 1.383(6) . ?
C30 H30C 0.9300 . ?
C31 H31C 0.9300 . ?
C25 C26 1.385(6) . ?
C25 H25C 0.9300 . ?
C21 C22 1.521(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C8 C7 1.523(6) . ?
C8 C9 1.531(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C3 C4 1.518(6) . ?
C3 C2 1.525(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C29 H29C 0.9300 . ?
C9 C10 1.525(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C7 C6 1.525(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C13 C14 1.521(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C15 C16 1.517(6) . ?
C15 C14 1.522(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C26 H26C 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C19 C18 1.530(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 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
O2 P1 O1 113.63(17) . . ?
O2 P1 O3 109.52(18) . . ?
O1 P1 O3 107.16(18) . . ?
O2 P1 C1 110.4(2) . . ?
O1 P1 C1 110.6(2) . . ?
O3 P1 C1 105.10(19) . . ?
O10 P4 O11 110.94(17) . . ?
O10 P4 O12 109.74(17) . . ?
O11 P4 O12 109.48(17) . . ?
O10 P4 C24 111.5(2) . . ?
O11 P4 C24 107.15(19) . . ?
O12 P4 C24 107.9(2) . . ?
O4 P2 O5 112.74(18) . . ?
O4 P2 O6 109.37(18) . . ?
O5 P2 O6 106.36(17) . . ?
O4 P2 C12 111.9(2) . . ?
O5 P2 C12 108.06(19) . . ?
O6 P2 C12 108.2(2) . . ?
P4 O11 H11 109.5 . . ?
P2 O5 H5 109.5 . . ?
P2 O6 H6 109.5 . . ?
P4 O12 H12 109.5 . . ?
P3 O9 H9 109.5 . . ?
P3 O8 H8 109.5 . . ?
P1 O3 H3 109.5 . . ?
O7 P3 O9 112.67(18) . . ?
O7 P3 O8 112.28(18) . . ?
O9 P3 O8 104.62(18) . . ?
O7 P3 C13 111.0(2) . . ?
O9 P3 C13 108.7(2) . . ?
O8 P3 C13 107.2(2) . . ?
C25 N1 C34 119.6(4) . . ?
C25 N1 H1 120.2 . . ?
C34 N1 H1 120.2 . . ?
C31 N2 C30 120.6(4) . . ?
C31 N2 H2 119.7 . . ?
C30 N2 H2 119.7 . . ?
C34 C33 C27 119.8(4) . . ?
C34 C33 H33C 120.1 . . ?
C27 C33 H33C 120.1 . . ?
C26 C27 C33 117.4(4) . . ?
C26 C27 C27 120.8(5) . 2_575 ?
C33 C27 C27 121.8(5) . 2_575 ?
C29 C28 C32 117.9(4) . . ?
C29 C28 C28 120.5(5) . 2_765 ?
C32 C28 C28 121.6(5) . 2_765 ?
C31 C32 C28 119.3(4) . . ?
C31 C32 H32C 120.3 . . ?
C28 C32 H32C 120.3 . . ?
C11 C12 P2 115.2(3) . . ?
C11 C12 H12A 108.5 . . ?
P2 C12 H12A 108.5 . . ?
C11 C12 H12B 108.5 . . ?
P2 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C23 C24 P4 116.6(3) . . ?
C23 C24 H24A 108.1 . . ?
P4 C24 H24A 108.1 . . ?
C23 C24 H24B 108.1 . . ?
P4 C24 H24B 108.1 . . ?
H24A C24 H24B 107.3 . . ?
C24 C23 C22 111.2(3) . . ?
C24 C23 H23A 109.4 . . ?
C22 C23 H23A 109.4 . . ?
C24 C23 H23B 109.4 . . ?
C22 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
C10 C11 C12 111.1(3) . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N1 C34 C33 121.7(4) . . ?
N1 C34 H34C 119.1 . . ?
C33 C34 H34C 119.1 . . ?
C2 C1 P1 115.7(3) . . ?
C2 C1 H1A 108.4 . . ?
P1 C1 H1A 108.4 . . ?
C2 C1 H1B 108.4 . . ?
P1 C1 H1B 108.4 . . ?
H1A C1 H1B 107.4 . . ?
C18 C17 C16 113.3(4) . . ?
C18 C17 H17A 108.9 . . ?
C16 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
C16 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C6 C5 C4 114.1(4) . . ?
C6 C5 H5A 108.7 . . ?
C4 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
C4 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C21 C20 C19 113.5(4) . . ?
C21 C20 H20A 108.9 . . ?
C19 C20 H20A 108.9 . . ?
C21 C20 H20B 108.9 . . ?
C19 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
N2 C30 C29 120.8(4) . . ?
N2 C30 H30C 119.6 . . ?
C29 C30 H30C 119.6 . . ?
N2 C31 C32 121.8(4) . . ?
N2 C31 H31C 119.1 . . ?
C32 C31 H31C 119.1 . . ?
N1 C25 C26 122.1(4) . . ?
N1 C25 H25C 118.9 . . ?
C26 C25 H25C 118.9 . . ?
C22 C21 C20 112.5(4) . . ?
C22 C21 H21A 109.1 . . ?
C20 C21 H21A 109.1 . . ?
C22 C21 H21B 109.1 . . ?
C20 C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
C7 C8 C9 114.3(4) . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C4 C3 C2 114.5(3) . . ?
C4 C3 H3A 108.6 . . ?
C2 C3 H3A 108.6 . . ?
C4 C3 H3B 108.6 . . ?
C2 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C3 C2 C1 111.0(3) . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C30 C29 C28 119.7(4) . . ?
C30 C29 H29C 120.1 . . ?
C28 C29 H29C 120.1 . . ?
C10 C9 C8 112.1(4) . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C8 C7 C6 112.9(4) . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C14 C13 P3 114.7(3) . . ?
C14 C13 H13A 108.6 . . ?
P3 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
P3 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C9 C10 C11 114.2(4) . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C16 C15 C14 112.6(4) . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C3 C4 C5 112.9(4) . . ?
C3 C4 H4A 109.0 . . ?
C5 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
C5 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C21 C22 C23 114.2(4) . . ?
C21 C22 H22A 108.7 . . ?
C23 C22 H22A 108.7 . . ?
C21 C22 H22B 108.7 . . ?
C23 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
C25 C26 C27 119.4(4) . . ?
C25 C26 H26C 120.3 . . ?
C27 C26 H26C 120.3 . . ?
C13 C14 C15 113.6(4) . . ?
C13 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
C13 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C20 C19 C18 113.1(4) . . ?
C20 C19 H19A 108.9 . . ?
C18 C19 H19A 108.9 . . ?
C20 C19 H19B 108.9 . . ?
C18 C19 H19B 108.9 . . ?
H19A C19 H19B 107.8 . . ?
C17 C18 C19 113.5(4) . . ?
C17 C18 H18A 108.9 . . ?
C19 C18 H18A 108.9 . . ?
C17 C18 H18B 108.9 . . ?
C19 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C15 C16 C17 114.1(4) . . ?
C15 C16 H16A 108.7 . . ?
C17 C16 H16A 108.7 . . ?
C15 C16 H16B 108.7 . . ?
C17 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C5 C6 C7 113.3(4) . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?

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
C34 C33 C27 C26 -0.5(6) . . . . ?
C34 C33 C27 C27 179.0(5) . . . 2_575 ?
C29 C28 C32 C31 0.1(6) . . . . ?
C28 C28 C32 C31 -179.9(5) 2_765 . . . ?
O4 P2 C12 C11 -54.3(4) . . . . ?
O5 P2 C12 C11 -179.0(3) . . . . ?
O6 P2 C12 C11 66.2(4) . . . . ?
O10 P4 C24 C23 -58.3(4) . . . . ?
O11 P4 C24 C23 -179.9(3) . . . . ?
O12 P4 C24 C23 62.3(4) . . . . ?
P4 C24 C23 C22 -178.3(3) . . . . ?
P2 C12 C11 C10 172.5(3) . . . . ?
C25 N1 C34 C33 1.9(7) . . . . ?
C27 C33 C34 N1 -0.9(7) . . . . ?
O2 P1 C1 C2 -69.0(4) . . . . ?
O1 P1 C1 C2 57.6(4) . . . . ?
O3 P1 C1 C2 172.9(3) . . . . ?
C31 N2 C30 C29 1.2(7) . . . . ?
C30 N2 C31 C32 -1.5(7) . . . . ?
C28 C32 C31 N2 0.8(7) . . . . ?
C34 N1 C25 C26 -1.5(7) . . . . ?
C19 C20 C21 C22 -176.7(4) . . . . ?
C4 C3 C2 C1 171.7(4) . . . . ?
P1 C1 C2 C3 -176.7(3) . . . . ?
N2 C30 C29 C28 -0.3(7) . . . . ?
C32 C28 C29 C30 -0.4(6) . . . . ?
C28 C28 C29 C30 179.6(5) 2_765 . . . ?
C7 C8 C9 C10 -178.7(4) . . . . ?
C9 C8 C7 C6 179.3(4) . . . . ?
O7 P3 C13 C14 -48.6(4) . . . . ?
O9 P3 C13 C14 75.9(4) . . . . ?
O8 P3 C13 C14 -171.6(3) . . . . ?
C8 C9 C10 C11 177.1(4) . . . . ?
C12 C11 C10 C9 -175.6(4) . . . . ?
C2 C3 C4 C5 -178.7(4) . . . . ?
C6 C5 C4 C3 176.9(4) . . . . ?
C20 C21 C22 C23 178.8(4) . . . . ?
C24 C23 C22 C21 -174.2(4) . . . . ?
N1 C25 C26 C27 0.1(7) . . . . ?
C33 C27 C26 C25 0.9(7) . . . . ?
C27 C27 C26 C25 -178.6(5) 2_575 . . . ?
P3 C13 C14 C15 -169.8(3) . . . . ?
C16 C15 C14 C13 -175.7(4) . . . . ?
C21 C20 C19 C18 179.4(4) . . . . ?
C16 C17 C18 C19 -178.8(4) . . . . ?
C20 C19 C18 C17 -178.8(4) . . . . ?
C14 C15 C16 C17 -176.3(4) . . . . ?
C18 C17 C16 C15 -178.9(4) . . . . ?
C4 C5 C6 C7 -179.9(4) . . . . ?
C8 C7 C6 C5 179.6(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O8 H8 O1 0.82 1.76 2.579(4) 173.7 .
O6 H6 O10 0.82 1.79 2.549(4) 153.6 .
N1 H1 N2 0.86 1.78 2.641(5) 175.7 .
N2 H2 N1 0.86 1.78 2.641(5) 177.9 .
O12 H12 O4 0.82 1.68 2.494(4) 171.4 1_545
O9 H9 O2 0.82 1.64 2.435(4) 162.2 1_545
O11 H11 O7 0.82 1.70 2.515(4) 176.1 2_656
O5 H5 O1 0.82 1.81 2.592(4) 158.5 2_666
O3 H3 O10 0.82 1.88 2.674(4) 162.0 2_566

_refine_diff_density_max         0.996
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.090

_shelxl_version_number           2014-3

