# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_19a
_database_code_depnum_ccdc_archive 'CCDC 1424112'
_audit_update_record             
;
2015-09-12 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H30 N4 O4 P2, 2(C H4 O)'
_chemical_formula_sum            'C30 H38 N4 O6 P2'
_chemical_formula_weight         612.58

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   10.4656(4)
_cell_length_b                   13.8598(5)
_cell_length_c                   11.2698(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.7680(10)
_cell_angle_gamma                90.00
_cell_volume                     1528.48(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7128
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      33.54

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.829
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19269
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         30.00
_reflns_number_total             4456
_reflns_number_gt                3628
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINTPlus, v. 6.2 (Bruker, 2001)'
_computing_data_reduction        'SAINTPlus, v. 6.2 (Bruker, 2001)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0547P)²+1.0689P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4456
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1284
_refine_ls_wR_factor_gt          0.1184
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.12951(4) 0.14028(3) 0.87508(4) 0.02173(11) Uani 1 1 d . . .
O1 O 0.16666(13) 0.09179(9) 0.77588(11) 0.0306(3) Uani 1 1 d . A .
N1 N 0.03770(14) 0.06977(9) 0.92754(12) 0.0224(3) Uani 1 1 d . A .
C1 C -0.01404(17) 0.10034(12) 1.02701(15) 0.0253(3) Uani 1 1 d . . .
H1A H -0.1139 0.1111 0.9895 0.030 Uiso 1 1 calc R A .
H1B H 0.0298 0.1619 1.0647 0.030 Uiso 1 1 calc R . .
C2 C -0.01641(18) -0.02366(12) 0.87053(15) 0.0266(3) Uani 1 1 d . . .
H2A H 0.0260 -0.0419 0.8079 0.032 Uiso 1 1 calc R A .
H2B H -0.1164 -0.0187 0.8255 0.032 Uiso 1 1 calc R . .
N2 N 0.25632(13) 0.18069(11) 0.99551(12) 0.0294(3) Uani 0.67 1 d P A 1
H2N H 0.2483 0.2407 1.0176 0.035 Uiso 0.67 1 d PR A 1
O2' O 0.25632(13) 0.18069(11) 0.99551(12) 0.0294(3) Uani 0.33 1 d P A 2
C3 C 0.32614(17) 0.12103(14) 1.09889(16) 0.0294(4) Uani 1 1 d . . .
C4 C 0.3508(2) 0.15687(17) 1.22034(18) 0.0399(5) Uani 1 1 d . A .
H4A H 0.3236 0.2205 1.2322 0.048 Uiso 1 1 calc R . .
C5 C 0.4157(3) 0.0980(2) 1.3238(2) 0.0579(7) Uani 1 1 d . . .
H5A H 0.4337 0.1218 1.4072 0.069 Uiso 1 1 calc R A .
C6 C 0.4541(3) 0.0061(2) 1.3072(2) 0.0652(8) Uani 1 1 d . A .
H6A H 0.4968 -0.0339 1.3788 0.078 Uiso 1 1 calc R . .
C7 C 0.4308(2) -0.02863(19) 1.1859(2) 0.0551(6) Uani 1 1 d . . .
H7A H 0.4585 -0.0922 1.1746 0.066 Uiso 1 1 calc R A .
C8 C 0.36717(19) 0.02915(15) 1.08091(19) 0.0375(4) Uani 1 1 d . A .
H8A H 0.3520 0.0058 0.9978 0.045 Uiso 1 1 calc R . .
O2 O 0.05293(14) 0.24312(9) 0.83359(13) 0.0322(3) Uani 0.67 1 d P A 1
N2' N 0.05293(14) 0.24312(9) 0.83359(13) 0.0322(3) Uani 0.33 1 d P A 2
H2N' H 0.0929 0.2954 0.9018 0.039 Uiso 0.33 1 d PR A 2
C9 C -0.08450(17) 0.25037(12) 0.75411(15) 0.0251(3) Uani 1 1 d . . .
C10 C -0.13888(19) 0.19402(15) 0.6475(2) 0.0392(5) Uani 1 1 d . A .
H10A H -0.0843 0.1465 0.6275 0.047 Uiso 1 1 calc R . .
C11 C -0.27458(19) 0.20708(16) 0.5691(2) 0.0406(5) Uani 1 1 d . . .
H11A H -0.3121 0.1683 0.4954 0.049 Uiso 1 1 calc R A .
C12 C -0.35423(19) 0.27495(15) 0.59682(19) 0.0362(4) Uani 1 1 d . A .
H12A H -0.4474 0.2823 0.5441 0.043 Uiso 1 1 calc R . .
C13 C -0.2981(2) 0.3328(2) 0.7021(2) 0.0520(6) Uani 1 1 d . . .
H13A H -0.3521 0.3815 0.7206 0.062 Uiso 1 1 calc R A .
C14 C -0.1635(2) 0.32034(17) 0.78117(19) 0.0440(5) Uani 1 1 d . A .
H14A H -0.1257 0.3600 0.8540 0.053 Uiso 1 1 calc R . .
O1S O 0.2296(4) 0.12529(16) 0.5715(3) 0.0571(8) Uani 0.67 1 d P B 1
C1S C 0.1749(5) 0.0399(5) 0.4933(5) 0.0372(10) Uani 0.67 1 d P B 1
H1SB H 0.0771 0.0391 0.4681 0.045 Uiso 0.67 1 d PR B 1
H1SC H 0.2106 -0.0185 0.5388 0.045 Uiso 0.67 1 d PR B 1
O2S O 0.1252(6) 0.1080(4) 0.5298(4) 0.0470(12) Uani 0.33 1 d P C 2
C2S C 0.2214(11) 0.0575(8) 0.5122(12) 0.055(3) Uani 0.33 1 d P C 2
H2SA H 0.2198 -0.0039 0.5512 0.066 Uiso 0.33 1 d PR C 2
H2SB H 0.3114 0.0837 0.5523 0.066 Uiso 0.33 1 d PR C 2
H1SA H 0.2078 0.0455 0.4207 0.066 Uiso 1 1 d R . .
H1S H 0.1777 0.1104 0.6296 0.066 Uiso 1 1 d R . .


_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 1.4700(12) . ?
P1 N2' 1.6206(14) . ?
P1 O2 1.6206(14) . ?
P1 N1 1.6220(13) . ?
P1 O2' 1.6247(13) . ?
P1 N2 1.6247(13) . ?
N1 C2 1.4671(19) . ?
N1 C1 1.4697(19) . ?
C1 C2 1.518(2) 3_557 ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C1 1.518(2) 3_557 ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
N2 C3 1.404(2) . ?
N2 H2N 0.8805 . ?
O2' C3 1.404(2) . ?
O2' H2N 0.8805 . ?
C3 C8 1.382(3) . ?
C3 C4 1.391(3) . ?
C4 C5 1.387(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.368(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.387(4) . ?
C6 H6A 0.9500 . ?
C7 C8 1.388(3) . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9500 . ?
O2 C9 1.403(2) . ?
O2 H2N' 1.0310 . ?
N2' C9 1.403(2) . ?
N2' H2N' 1.0310 . ?
C9 C10 1.376(2) . ?
C9 C14 1.377(3) . ?
C10 C11 1.393(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.365(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.379(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.385(3) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
O1S C1S 1.466(6) . ?
O1S H1S 1.0093 . ?
C1S H1SB 0.9601 . ?
C1S H1SC 0.9600 . ?
C1S H1SA 0.9978 . ?
O2S C2S 1.299(12) . ?
O2S H1S 1.0624 . ?
C2S H2SA 0.9599 . ?
C2S H2SB 0.9601 . ?
C2S H1SA 1.0042 . ?

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 N2' 114.82(8) . . ?
O1 P1 O2 114.82(8) . . ?
N2' P1 O2 0.00(9) . . ?
O1 P1 N1 110.63(7) . . ?
N2' P1 N1 109.80(7) . . ?
O2 P1 N1 109.80(7) . . ?
O1 P1 O2' 115.78(8) . . ?
N2' P1 O2' 96.42(7) . . ?
O2 P1 O2' 96.42(7) . . ?
N1 P1 O2' 108.49(7) . . ?
O1 P1 N2 115.78(8) . . ?
N2' P1 N2 96.42(7) . . ?
O2 P1 N2 96.42(7) . . ?
N1 P1 N2 108.49(7) . . ?
O2' P1 N2 0.00(8) . . ?
C2 N1 C1 113.53(12) . . ?
C2 N1 P1 123.97(10) . . ?
C1 N1 P1 122.03(10) . . ?
N1 C1 C2 110.10(13) . 3_557 ?
N1 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 3_557 . ?
N1 C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 3_557 . ?
H1A C1 H1B 108.2 . . ?
N1 C2 C1 109.91(13) . 3_557 ?
N1 C2 H2A 109.7 . . ?
C1 C2 H2A 109.7 3_557 . ?
N1 C2 H2B 109.7 . . ?
C1 C2 H2B 109.7 3_557 . ?
H2A C2 H2B 108.2 . . ?
C3 N2 P1 121.39(12) . . ?
C3 N2 H2N 113.3 . . ?
P1 N2 H2N 115.5 . . ?
C3 O2' P1 121.39(12) . . ?
C3 O2' H2N 113.3 . . ?
P1 O2' H2N 115.5 . . ?
C8 C3 C4 120.96(18) . . ?
C8 C3 N2 121.23(16) . . ?
C4 C3 N2 117.80(18) . . ?
C8 C3 O2' 121.23(16) . . ?
C4 C3 O2' 117.80(18) . . ?
N2 C3 O2' 0.00(16) . . ?
C5 C4 C3 118.8(2) . . ?
C5 C4 H4A 120.6 . . ?
C3 C4 H4A 120.6 . . ?
C6 C5 C4 120.9(2) . . ?
C6 C5 H5A 119.6 . . ?
C4 C5 H5A 119.6 . . ?
C5 C6 C7 120.0(2) . . ?
C5 C6 H6A 120.0 . . ?
C7 C6 H6A 120.0 . . ?
C6 C7 C8 120.2(3) . . ?
C6 C7 H7A 119.9 . . ?
C8 C7 H7A 119.9 . . ?
C3 C8 C7 119.1(2) . . ?
C3 C8 H8A 120.4 . . ?
C7 C8 H8A 120.4 . . ?
C9 O2 P1 122.51(11) . . ?
C9 O2 H2N' 118.6 . . ?
P1 O2 H2N' 112.0 . . ?
C9 N2' P1 122.51(11) . . ?
C9 N2' H2N' 118.6 . . ?
P1 N2' H2N' 112.0 . . ?
C10 C9 C14 119.89(17) . . ?
C10 C9 N2' 122.01(16) . . ?
C14 C9 N2' 117.99(16) . . ?
C10 C9 O2 122.01(16) . . ?
C14 C9 O2 117.99(16) . . ?
N2' C9 O2 0.00(16) . . ?
C9 C10 C11 119.55(18) . . ?
C9 C10 H10A 120.2 . . ?
C11 C10 H10A 120.2 . . ?
C12 C11 C10 120.83(18) . . ?
C12 C11 H11A 119.6 . . ?
C10 C11 H11A 119.6 . . ?
C11 C12 C13 119.29(18) . . ?
C11 C12 H12A 120.4 . . ?
C13 C12 H12A 120.4 . . ?
C12 C13 C14 120.5(2) . . ?
C12 C13 H13A 119.8 . . ?
C14 C13 H13A 119.8 . . ?
C9 C14 C13 119.93(18) . . ?
C9 C14 H14A 120.0 . . ?
C13 C14 H14A 120.0 . . ?
C1S O1S H2SB 68.3 . . ?
C1S O1S H1S 92.2 . . ?
H2SB O1S H1S 130.3 . . ?
O1S C1S H1SB 109.6 . . ?
O1S C1S H1SC 111.4 . . ?
H1SB C1S H1SC 108.8 . . ?
O1S C1S H2SA 96.7 . . ?
H1SB C1S H2SA 116.0 . . ?
H1SC C1S H2SA 14.7 . . ?
O1S C1S H2SB 44.5 . . ?
H1SB C1S H2SB 153.8 . . ?
H1SC C1S H2SB 88.6 . . ?
H2SA C1S H2SB 77.0 . . ?
O1S C1S H1SA 104.8 . . ?
H1SB C1S H1SA 113.6 . . ?
H1SC C1S H1SA 108.8 . . ?
H2SA C1S H1SA 114.0 . . ?
H2SB C1S H1SA 77.1 . . ?
C2S O2S H1SB 70.5 . . ?
C2S O2S H1S 92.3 . . ?
H1SB O2S H1S 126.9 . . ?
O2S C2S H1SB 51.0 . . ?
O2S C2S H1SC 108.1 . . ?
H1SB C2S H1SC 74.4 . . ?
O2S C2S H2SA 105.5 . . ?
H1SB C2S H2SA 79.3 . . ?
H1SC C2S H2SA 10.7 . . ?
O2S C2S H2SB 114.1 . . ?
H1SB C2S H2SB 165.1 . . ?
H1SC C2S H2SB 114.1 . . ?
H2SA C2S H2SB 107.1 . . ?
O2S C2S H1SA 114.3 . . ?
H1SB C2S H1SA 82.3 . . ?
H1SC C2S H1SA 97.4 . . ?
H2SA C2S H1SA 107.7 . . ?
H2SB C2S H1SA 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
O1 P1 N1 C2 -8.11(16) . . . . ?
N2' P1 N1 C2 119.65(14) . . . . ?
O2 P1 N1 C2 119.65(14) . . . . ?
O2' P1 N1 C2 -136.13(14) . . . . ?
N2 P1 N1 C2 -136.13(14) . . . . ?
O1 P1 N1 C1 -179.72(12) . . . . ?
N2' P1 N1 C1 -51.96(14) . . . . ?
O2 P1 N1 C1 -51.96(14) . . . . ?
O2' P1 N1 C1 52.26(15) . . . . ?
N2 P1 N1 C1 52.26(15) . . . . ?
C2 N1 C1 C2 56.30(19) . . . 3_557 ?
P1 N1 C1 C2 -131.28(13) . . . 3_557 ?
C1 N1 C2 C1 -56.20(19) . . . 3_557 ?
P1 N1 C2 C1 131.56(13) . . . 3_557 ?
O1 P1 N2 C3 -85.16(15) . . . . ?
N2' P1 N2 C3 153.27(14) . . . . ?
O2 P1 N2 C3 153.27(14) . . . . ?
N1 P1 N2 C3 39.87(16) . . . . ?
O2' P1 N2 C3 0(6) . . . . ?
O1 P1 O2' C3 -85.16(15) . . . . ?
N2' P1 O2' C3 153.27(14) . . . . ?
O2 P1 O2' C3 153.27(14) . . . . ?
N1 P1 O2' C3 39.87(16) . . . . ?
N2 P1 O2' C3 0(6) . . . . ?
P1 N2 C3 C8 46.1(2) . . . . ?
P1 N2 C3 C4 -132.82(15) . . . . ?
P1 N2 C3 O2' 0(100) . . . . ?
P1 O2' C3 C8 46.1(2) . . . . ?
P1 O2' C3 C4 -132.82(15) . . . . ?
P1 O2' C3 N2 0(100) . . . . ?
C8 C3 C4 C5 -1.0(3) . . . . ?
N2 C3 C4 C5 177.95(17) . . . . ?
O2' C3 C4 C5 177.95(17) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 C7 1.3(4) . . . . ?
C5 C6 C7 C8 -0.7(4) . . . . ?
C4 C3 C8 C7 1.6(3) . . . . ?
N2 C3 C8 C7 -177.32(18) . . . . ?
O2' C3 C8 C7 -177.32(18) . . . . ?
C6 C7 C8 C3 -0.7(3) . . . . ?
O1 P1 O2 C9 75.58(15) . . . . ?
N2' P1 O2 C9 0(4) . . . . ?
N1 P1 O2 C9 -49.81(15) . . . . ?
O2' P1 O2 C9 -162.13(14) . . . . ?
N2 P1 O2 C9 -162.13(14) . . . . ?
O1 P1 N2' C9 75.58(15) . . . . ?
O2 P1 N2' C9 0(4) . . . . ?
N1 P1 N2' C9 -49.81(15) . . . . ?
O2' P1 N2' C9 -162.13(14) . . . . ?
N2 P1 N2' C9 -162.13(14) . . . . ?
P1 N2' C9 C10 -43.0(2) . . . . ?
P1 N2' C9 C14 140.87(16) . . . . ?
P1 N2' C9 O2 0(100) . . . . ?
P1 O2 C9 C10 -43.0(2) . . . . ?
P1 O2 C9 C14 140.87(16) . . . . ?
P1 O2 C9 N2' 0(100) . . . . ?
C14 C9 C10 C11 -1.3(3) . . . . ?
N2' C9 C10 C11 -177.33(19) . . . . ?
O2 C9 C10 C11 -177.33(19) . . . . ?
C9 C10 C11 C12 -0.1(4) . . . . ?
C10 C11 C12 C13 1.7(4) . . . . ?
C11 C12 C13 C14 -1.9(4) . . . . ?
C10 C9 C14 C13 1.0(3) . . . . ?
N2' C9 C14 C13 177.3(2) . . . . ?
O2 C9 C14 C13 177.3(2) . . . . ?
C12 C13 C14 C9 0.6(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
_geom_hbond_publ_flag
O1S H1S O1 1.01 1.71 2.652(4) 153 . yes
N2 H2N O1S 0.88 1.99 2.866(3) 178 4_566 yes
O2S H1S O1 1.06 1.71 2.660(7) 146 . yes
N2' H2N' O2S 1.03 1.91 2.921(6) 167 4_566 yes


_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_11a
_database_code_depnum_ccdc_archive 'CCDC 1027076'
_audit_update_record             
;
2015-09-12 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H30 N4 O4 P2'
_chemical_formula_sum            'C28 H30 N4 O4 P2'
_chemical_formula_weight         548.50

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   9.422(3)
_cell_length_b                   10.045(3)
_cell_length_c                   14.165(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.264(5)
_cell_angle_gamma                90.00
_cell_volume                     1336.9(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1145
_cell_measurement_theta_min      3
_cell_measurement_theta_max      29

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.939
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  "Bruker APEX II Duo CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14599
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         29.00
_reflns_number_total             3554
_reflns_number_gt                2769
_reflns_threshold_expression     I>2σ(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0517P)²+1.1612P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3554
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1172
_refine_ls_wR_factor_gt          0.1029
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.968
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.04532(5) 0.43244(4) 0.20564(3) 0.02280(13) Uani 1 1 d . . .
N1 N -0.09579(18) 0.49885(15) 0.24857(10) 0.0258(3) Uani 1 1 d . . .
H1N H -0.087(3) 0.580(3) 0.2619(19) 0.049(7) Uiso 1 1 d . . .
O1 O 0.06141(14) 0.28771(12) 0.21890(9) 0.0263(3) Uani 1 1 d . . .
C1 C 0.0165(2) 0.61277(17) 0.06232(12) 0.0305(4) Uani 1 1 d . . .
H1A H 0.1051 0.6546 0.0433 0.037 Uiso 1 1 calc R . .
H1B H -0.0189 0.6659 0.1145 0.037 Uiso 1 1 calc R . .
N2 N 0.04624(19) 0.47543(15) 0.09481(10) 0.0281(4) Uani 1 1 d . . .
O2 O 0.17114(15) 0.51769(13) 0.25885(9) 0.0286(3) Uani 1 1 d . . .
C4 C 0.0939(2) 0.38895(18) 0.02089(12) 0.0274(4) Uani 1 1 d . . .
H4A H 0.1086 0.2976 0.0459 0.033 Uiso 1 1 calc R . .
H4B H 0.1857 0.4217 0.0002 0.033 Uiso 1 1 calc R . .
C5 C 0.2142(2) 0.49236(17) 0.35503(12) 0.0246(4) Uani 1 1 d . . .
C6 C 0.3283(2) 0.40802(19) 0.37438(13) 0.0305(4) Uani 1 1 d . . .
H6A H 0.3748 0.3677 0.3244 0.037 Uiso 1 1 calc R . .
C7 C 0.3739(2) 0.3832(2) 0.46810(15) 0.0361(5) Uani 1 1 d . . .
H7A H 0.4507 0.3236 0.4826 0.043 Uiso 1 1 calc R . .
C8 C 0.3083(2) 0.4447(2) 0.54064(13) 0.0346(4) Uani 1 1 d . . .
H8A H 0.3399 0.4273 0.6047 0.041 Uiso 1 1 calc R . .
C9 C 0.1968(2) 0.5314(2) 0.51965(14) 0.0352(4) Uani 1 1 d . . .
H9A H 0.1527 0.5745 0.5695 0.042 Uiso 1 1 calc R . .
C10 C 0.1487(2) 0.5562(2) 0.42611(14) 0.0311(4) Uani 1 1 d . . .
H10A H 0.0720 0.6159 0.4115 0.037 Uiso 1 1 calc R . .
C11 C -0.2353(2) 0.46302(18) 0.21337(12) 0.0255(4) Uani 1 1 d . . .
C12 C -0.2764(2) 0.3304(2) 0.20565(17) 0.0391(5) Uani 1 1 d . . .
H12A H -0.2110 0.2619 0.2247 0.047 Uiso 1 1 calc R . .
C13 C -0.4131(3) 0.2984(2) 0.17016(19) 0.0475(6) Uani 1 1 d . . .
H13A H -0.4401 0.2075 0.1641 0.057 Uiso 1 1 calc R . .
C14 C -0.5100(2) 0.3958(3) 0.14367(17) 0.0450(6) Uani 1 1 d . . .
H14A H -0.6032 0.3729 0.1187 0.054 Uiso 1 1 calc R . .
C15 C -0.4704(3) 0.5272(3) 0.15373(19) 0.0491(6) Uani 1 1 d . . .
H15A H -0.5376 0.5953 0.1369 0.059 Uiso 1 1 calc R . .
C16 C -0.3336(2) 0.5616(2) 0.18812(17) 0.0393(5) Uani 1 1 d . . .
H16A H -0.3074 0.6527 0.1944 0.047 Uiso 1 1 calc R . .


_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 1.4722(13) . ?
P1 O2 1.6044(14) . ?
P1 N2 1.6287(15) . ?
P1 N1 1.6441(17) . ?
N1 C11 1.417(2) . ?
N1 H1N 0.84(3) . ?
C1 N2 1.475(2) . ?
C1 C4 1.513(3) 3_565 ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
N2 C4 1.457(2) . ?
O2 C5 1.415(2) . ?
C4 C1 1.513(3) 3_565 ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.378(3) . ?
C5 C6 1.380(3) . ?
C6 C7 1.387(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.383(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.380(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.391(3) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C16 1.385(3) . ?
C11 C12 1.389(3) . ?
C12 C13 1.385(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.372(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.377(4) . ?
C14 H14A 0.9500 . ?
C15 C16 1.387(3) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 O2 113.68(7) . . ?
O1 P1 N2 112.14(8) . . ?
O2 P1 N2 104.75(8) . . ?
O1 P1 N1 115.59(8) . . ?
O2 P1 N1 101.49(8) . . ?
N2 P1 N1 108.14(8) . . ?
C11 N1 P1 121.42(12) . . ?
C11 N1 H1N 113.5(18) . . ?
P1 N1 H1N 114.1(19) . . ?
N2 C1 C4 109.64(15) . 3_565 ?
N2 C1 H1A 109.7 . . ?
C4 C1 H1A 109.7 3_565 . ?
N2 C1 H1B 109.7 . . ?
C4 C1 H1B 109.7 3_565 . ?
H1A C1 H1B 108.2 . . ?
C4 N2 C1 113.26(14) . . ?
C4 N2 P1 123.96(12) . . ?
C1 N2 P1 122.30(12) . . ?
C5 O2 P1 120.36(11) . . ?
N2 C4 C1 109.61(16) . 3_565 ?
N2 C4 H4A 109.7 . . ?
C1 C4 H4A 109.7 3_565 . ?
N2 C4 H4B 109.7 . . ?
C1 C4 H4B 109.7 3_565 . ?
H4A C4 H4B 108.2 . . ?
C10 C5 C6 121.68(17) . . ?
C10 C5 O2 120.51(17) . . ?
C6 C5 O2 117.71(17) . . ?
C5 C6 C7 118.80(19) . . ?
C5 C6 H6A 120.6 . . ?
C7 C6 H6A 120.6 . . ?
C8 C7 C6 120.45(19) . . ?
C8 C7 H7A 119.8 . . ?
C6 C7 H7A 119.8 . . ?
C9 C8 C7 119.79(18) . . ?
C9 C8 H8A 120.1 . . ?
C7 C8 H8A 120.1 . . ?
C8 C9 C10 120.49(19) . . ?
C8 C9 H9A 119.8 . . ?
C10 C9 H9A 119.8 . . ?
C5 C10 C9 118.74(19) . . ?
C5 C10 H10A 120.6 . . ?
C9 C10 H10A 120.6 . . ?
C16 C11 C12 119.22(19) . . ?
C16 C11 N1 119.62(18) . . ?
C12 C11 N1 121.14(17) . . ?
C13 C12 C11 119.8(2) . . ?
C13 C12 H12A 120.1 . . ?
C11 C12 H12A 120.1 . . ?
C14 C13 C12 121.1(2) . . ?
C14 C13 H13A 119.5 . . ?
C12 C13 H13A 119.5 . . ?
C13 C14 C15 119.1(2) . . ?
C13 C14 H14A 120.5 . . ?
C15 C14 H14A 120.5 . . ?
C14 C15 C16 120.9(2) . . ?
C14 C15 H15A 119.6 . . ?
C16 C15 H15A 119.6 . . ?
C11 C16 C15 119.9(2) . . ?
C11 C16 H16A 120.0 . . ?
C15 C16 H16A 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
O1 P1 N1 C11 -63.20(16) . . . . ?
O2 P1 N1 C11 173.31(13) . . . . ?
N2 P1 N1 C11 63.43(16) . . . . ?
C4 C1 N2 C4 57.2(2) 3_565 . . . ?
C4 C1 N2 P1 -130.35(15) 3_565 . . . ?
O1 P1 N2 C4 -15.05(19) . . . . ?
O2 P1 N2 C4 108.70(17) . . . . ?
N1 P1 N2 C4 -143.66(16) . . . . ?
O1 P1 N2 C1 173.34(15) . . . . ?
O2 P1 N2 C1 -62.91(18) . . . . ?
N1 P1 N2 C1 44.74(18) . . . . ?
O1 P1 O2 C5 -48.58(16) . . . . ?
N2 P1 O2 C5 -171.34(14) . . . . ?
N1 P1 O2 C5 76.20(15) . . . . ?
C1 N2 C4 C1 -57.2(2) . . . 3_565 ?
P1 N2 C4 C1 130.51(15) . . . 3_565 ?
P1 O2 C5 C10 -88.41(19) . . . . ?
P1 O2 C5 C6 95.10(18) . . . . ?
C10 C5 C6 C7 2.6(3) . . . . ?
O2 C5 C6 C7 179.04(17) . . . . ?
C5 C6 C7 C8 -1.6(3) . . . . ?
C6 C7 C8 C9 -0.1(3) . . . . ?
C7 C8 C9 C10 0.8(3) . . . . ?
C6 C5 C10 C9 -1.8(3) . . . . ?
O2 C5 C10 C9 -178.19(17) . . . . ?
C8 C9 C10 C5 0.1(3) . . . . ?
P1 N1 C11 C16 -130.40(17) . . . . ?
P1 N1 C11 C12 51.0(2) . . . . ?
C16 C11 C12 C13 2.1(3) . . . . ?
N1 C11 C12 C13 -179.4(2) . . . . ?
C11 C12 C13 C14 -1.0(4) . . . . ?
C12 C13 C14 C15 -0.7(4) . . . . ?
C13 C14 C15 C16 1.4(4) . . . . ?
C12 C11 C16 C15 -1.3(3) . . . . ?
N1 C11 C16 C15 -179.9(2) . . . . ?
C14 C15 C16 C11 -0.4(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
_geom_hbond_publ_flag
N1 H1N O1 0.84(3) 2.12(3) 2.952(2) 174(3) 2_555 ?


_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        29.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.056




####################################################################### 
# 
# 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_28a
_database_code_depnum_ccdc_archive 'CCDC 1027078'
_audit_update_record             
;
2015-09-12 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H30 N4 O4 P2'
_chemical_formula_sum            'C28 H30 N4 O4 P2'
_chemical_formula_weight         548.50

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_chemical_absolute_configuration ad


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

_cell_length_a                   12.9321(4)
_cell_length_b                   19.0714(6)
_cell_length_c                   21.9285(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5408.3(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1299
_cell_measurement_theta_min      3
_cell_measurement_theta_max      29

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2304
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  "Bruker APEX II Duo CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48787
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         29.00
_reflns_number_total             14384
_reflns_number_gt                12885
_reflns_threshold_expression     I>2σ(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0502P)²+0.8232P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_number_reflns         14384
_refine_ls_number_parameters     702
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0900
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1A P 0.45129(3) 0.578070(17) -0.081834(16) 0.01553(7) Uani 1 1 d . . .
P2A P 0.79551(3) 0.675076(17) 0.078187(16) 0.01603(7) Uani 1 1 d . . .
O1A O 0.45525(8) 0.50064(5) -0.08347(5) 0.0200(2) Uani 1 1 d . . .
O2A O 0.79311(8) 0.75203(5) 0.08505(5) 0.0210(2) Uani 1 1 d . . .
O3A O 0.44223(8) 0.61465(5) -0.14720(4) 0.0195(2) Uani 1 1 d . . .
O4A O 0.79952(8) 0.63302(5) 0.14193(5) 0.0228(2) Uani 1 1 d . . .
N1A N 0.35097(9) 0.61236(6) -0.04719(5) 0.0186(2) Uani 1 1 d . . .
N2A N 0.90040(9) 0.64155(7) 0.04820(6) 0.0202(2) Uani 1 1 d . . .
N3A N 0.55728(9) 0.60981(6) -0.05299(6) 0.0184(2) Uani 1 1 d . . .
N4A N 0.69586(9) 0.64733(6) 0.03935(6) 0.0184(2) Uani 1 1 d . . .
C1A C 0.56863(11) 0.68395(7) -0.03636(7) 0.0206(3) Uani 1 1 d . . .
H1AA H 0.5021 0.7087 -0.0423 0.025 Uiso 1 1 calc R . .
H1AB H 0.6212 0.7064 -0.0627 0.025 Uiso 1 1 calc R . .
C2A C 0.60171(11) 0.68894(7) 0.03021(7) 0.0202(3) Uani 1 1 d . . .
H2AA H 0.6150 0.7385 0.0411 0.024 Uiso 1 1 calc R . .
H2AB H 0.5458 0.6711 0.0569 0.024 Uiso 1 1 calc R . .
C3A C 0.68487(11) 0.57304(7) 0.02281(6) 0.0183(3) Uani 1 1 d . . .
H3AA H 0.6326 0.5505 0.0493 0.022 Uiso 1 1 calc R . .
H3AB H 0.7516 0.5485 0.0286 0.022 Uiso 1 1 calc R . .
C4A C 0.65129(11) 0.56810(7) -0.04390(6) 0.0179(3) Uani 1 1 d . . .
H4AA H 0.7071 0.5859 -0.0706 0.021 Uiso 1 1 calc R . .
H4AB H 0.6378 0.5186 -0.0547 0.021 Uiso 1 1 calc R . .
C5A C 0.35950(11) 0.60623(7) -0.18801(7) 0.0205(3) Uani 1 1 d . . .
C6A C 0.35259(15) 0.65675(9) -0.23334(8) 0.0336(4) Uani 1 1 d . . .
H6AA H 0.4007 0.6943 -0.2348 0.040 Uiso 1 1 calc R . .
C7A C 0.27458(18) 0.65170(9) -0.27644(9) 0.0450(5) Uani 1 1 d . . .
H7AA H 0.2692 0.6860 -0.3077 0.054 Uiso 1 1 calc R . .
C8A C 0.20390(17) 0.59654(9) -0.27430(10) 0.0444(5) Uani 1 1 d . . .
H8AA H 0.1498 0.5935 -0.3035 0.053 Uiso 1 1 calc R . .
C9A C 0.21345(14) 0.54625(9) -0.22918(9) 0.0377(4) Uani 1 1 d . . .
H9AA H 0.1660 0.5083 -0.2280 0.045 Uiso 1 1 calc R . .
C10A C 0.29152(12) 0.55030(8) -0.18538(7) 0.0266(3) Uani 1 1 d . . .
H10A H 0.2978 0.5156 -0.1546 0.032 Uiso 1 1 calc R . .
C11A C 0.32123(11) 0.60068(7) 0.01393(6) 0.0179(3) Uani 1 1 d . . .
C12A C 0.23449(12) 0.63581(8) 0.03566(7) 0.0227(3) Uani 1 1 d . . .
H12A H 0.1977 0.6667 0.0095 0.027 Uiso 1 1 calc R . .
C13A C 0.20118(14) 0.62613(9) 0.09527(8) 0.0319(4) Uani 1 1 d . . .
H13A H 0.1411 0.6498 0.1094 0.038 Uiso 1 1 calc R . .
C17A C 0.70805(12) 0.62548(8) 0.17540(6) 0.0225(3) Uani 1 1 d . . .
C14A C 0.25506(14) 0.58205(9) 0.13442(7) 0.0326(4) Uani 1 1 d . . .
H14A H 0.2332 0.5760 0.1754 0.039 Uiso 1 1 calc R . .
C15A C 0.34138(13) 0.54696(9) 0.11256(7) 0.0284(3) Uani 1 1 d . . .
H15A H 0.3784 0.5165 0.1390 0.034 Uiso 1 1 calc R . .
C16A C 0.37482(11) 0.55551(8) 0.05284(7) 0.0233(3) Uani 1 1 d . . .
H16A H 0.4338 0.5308 0.0385 0.028 Uiso 1 1 calc R . .
C18A C 0.65455(14) 0.68400(8) 0.19590(7) 0.0294(3) Uani 1 1 d . . .
H18A H 0.6795 0.7299 0.1877 0.035 Uiso 1 1 calc R . .
C19A C 0.56384(15) 0.67404(10) 0.22868(8) 0.0354(4) Uani 1 1 d . . .
H19A H 0.5260 0.7135 0.2428 0.043 Uiso 1 1 calc R . .
C20A C 0.52804(15) 0.60691(10) 0.24102(8) 0.0354(4) Uani 1 1 d . . .
H20A H 0.4656 0.6005 0.2631 0.042 Uiso 1 1 calc R . .
C21A C 0.58351(13) 0.54934(9) 0.22104(8) 0.0312(3) Uani 1 1 d . . .
H21A H 0.5593 0.5034 0.2299 0.037 Uiso 1 1 calc R . .
C22A C 0.67421(13) 0.55803(8) 0.18812(7) 0.0252(3) Uani 1 1 d . . .
H22A H 0.7125 0.5185 0.1745 0.030 Uiso 1 1 calc R . .
C23A C 0.93018(11) 0.65039(7) -0.01317(7) 0.0203(3) Uani 1 1 d . . .
C24A C 0.88770(12) 0.70224(8) -0.05070(7) 0.0228(3) Uani 1 1 d . . .
H24A H 0.8366 0.7332 -0.0351 0.027 Uiso 1 1 calc R . .
C25A C 0.92053(13) 0.70841(9) -0.11096(7) 0.0275(3) Uani 1 1 d . . .
H25A H 0.8912 0.7436 -0.1363 0.033 Uiso 1 1 calc R . .
C26A C 0.99546(13) 0.66386(9) -0.13446(8) 0.0300(3) Uani 1 1 d . . .
H26A H 1.0173 0.6682 -0.1756 0.036 Uiso 1 1 calc R . .
C27A C 1.03806(13) 0.61275(9) -0.09681(8) 0.0294(3) Uani 1 1 d . . .
H27A H 1.0898 0.5823 -0.1124 0.035 Uiso 1 1 calc R . .
C28A C 1.00599(12) 0.60576(8) -0.03696(8) 0.0243(3) Uani 1 1 d . . .
H28A H 1.0356 0.5705 -0.0119 0.029 Uiso 1 1 calc R . .
P1 P 0.19877(3) 0.668247(17) 0.424178(16) 0.01668(7) Uani 1 1 d . . .
P2 P 0.56032(3) 0.576853(18) 0.579217(16) 0.01702(7) Uani 1 1 d . . .
O1 O 0.20056(8) 0.74501(5) 0.41624(4) 0.0196(2) Uani 1 1 d . . .
O2 O 0.19969(8) 0.62518(5) 0.36122(5) 0.0219(2) Uani 1 1 d . . .
O3 O 0.56362(8) 0.50004(5) 0.58489(5) 0.0241(2) Uani 1 1 d . . .
O4 O 0.55765(9) 0.61743(5) 0.64290(5) 0.0237(2) Uani 1 1 d . . .
N1 N 0.09571(10) 0.63554(7) 0.45781(6) 0.0203(2) Uani 1 1 d . . .
N2 N 0.66094(10) 0.61307(7) 0.54591(6) 0.0229(3) Uani 1 1 d . . .
N3 N 0.29922(10) 0.64077(6) 0.46205(6) 0.0192(2) Uani 1 1 d . . .
N4 N 0.45734(10) 0.60373(6) 0.54323(6) 0.0202(2) Uani 1 1 d . . .
C1 C 0.31025(11) 0.56738(7) 0.48175(7) 0.0209(3) Uani 1 1 d . . .
H1A H 0.3540 0.5415 0.4523 0.025 Uiso 1 1 calc R . .
H1B H 0.2415 0.5446 0.4830 0.025 Uiso 1 1 calc R . .
C2 C 0.35939(11) 0.56506(7) 0.54474(7) 0.0206(3) Uani 1 1 d . . .
H2A H 0.3122 0.5865 0.5750 0.025 Uiso 1 1 calc R . .
H2B H 0.3721 0.5158 0.5568 0.025 Uiso 1 1 calc R . .
C3 C 0.44437(12) 0.67729(7) 0.52498(7) 0.0236(3) Uani 1 1 d . . .
H3A H 0.5122 0.7013 0.5250 0.028 Uiso 1 1 calc R . .
H3B H 0.3984 0.7017 0.5542 0.028 Uiso 1 1 calc R . .
C4 C 0.39732(11) 0.67960(7) 0.46116(7) 0.0203(3) Uani 1 1 d . . .
H4A H 0.3849 0.7288 0.4488 0.024 Uiso 1 1 calc R . .
H4B H 0.4454 0.6581 0.4314 0.024 Uiso 1 1 calc R . .
C5 C 0.13756(11) 0.64635(7) 0.31137(6) 0.0196(3) Uani 1 1 d . . .
C6 C 0.17373(13) 0.69926(8) 0.27397(7) 0.0268(3) Uani 1 1 d . . .
H6A H 0.2384 0.7211 0.2819 0.032 Uiso 1 1 calc R . .
C7 C 0.11375(14) 0.72003(8) 0.22438(7) 0.0296(3) Uani 1 1 d . . .
H7A H 0.1364 0.7574 0.1990 0.036 Uiso 1 1 calc R . .
C8 C 0.02134(13) 0.68653(8) 0.21190(7) 0.0256(3) Uani 1 1 d . . .
H8A H -0.0190 0.7003 0.1777 0.031 Uiso 1 1 calc R . .
C9 C -0.01216(12) 0.63264(9) 0.24953(7) 0.0281(3) Uani 1 1 d . . .
H9A H -0.0753 0.6093 0.2406 0.034 Uiso 1 1 calc R . .
C10 C 0.04514(12) 0.61232(8) 0.29999(7) 0.0256(3) Uani 1 1 d . . .
H10B H 0.0215 0.5759 0.3261 0.031 Uiso 1 1 calc R . .
C11 C 0.06524(11) 0.64939(7) 0.51796(7) 0.0197(3) Uani 1 1 d . . .
C12 C -0.01543(11) 0.60962(8) 0.54345(8) 0.0230(3) Uani 1 1 d . . .
H12B H -0.0473 0.5737 0.5200 0.028 Uiso 1 1 calc R . .
C13 C -0.04873(13) 0.62224(8) 0.60224(8) 0.0284(3) Uani 1 1 d . . .
H13B H -0.1027 0.5945 0.6190 0.034 Uiso 1 1 calc R . .
C14 C -0.00405(13) 0.67514(9) 0.63720(8) 0.0286(3) Uani 1 1 d . . .
H14B H -0.0278 0.6840 0.6775 0.034 Uiso 1 1 calc R . .
C15 C 0.07595(12) 0.71501(8) 0.61241(7) 0.0249(3) Uani 1 1 d . . .
H15B H 0.1070 0.7511 0.6360 0.030 Uiso 1 1 calc R . .
C16 C 0.11060(11) 0.70246(8) 0.55346(7) 0.0215(3) Uani 1 1 d . . .
H16B H 0.1652 0.7299 0.5371 0.026 Uiso 1 1 calc R . .
C17 C 0.62474(11) 0.60204(7) 0.69175(6) 0.0201(3) Uani 1 1 d . . .
C18 C 0.58883(12) 0.55786(8) 0.73702(7) 0.0243(3) Uani 1 1 d . . .
H18B H 0.5240 0.5349 0.7329 0.029 Uiso 1 1 calc R . .
C19 C 0.64948(12) 0.54773(8) 0.78873(7) 0.0263(3) Uani 1 1 d . . .
H19B H 0.6256 0.5177 0.8203 0.032 Uiso 1 1 calc R . .
C20 C 0.74385(12) 0.58077(8) 0.79462(7) 0.0252(3) Uani 1 1 d . . .
H20B H 0.7845 0.5739 0.8302 0.030 Uiso 1 1 calc R . .
C21 C 0.77921(12) 0.62428(8) 0.74798(7) 0.0244(3) Uani 1 1 d . . .
H21B H 0.8444 0.6469 0.7517 0.029 Uiso 1 1 calc R . .
C22 C 0.71964(12) 0.63476(7) 0.69611(7) 0.0233(3) Uani 1 1 d . . .
H22B H 0.7438 0.6640 0.6641 0.028 Uiso 1 1 calc R . .
C23 C 0.68767(11) 0.60582(8) 0.48362(7) 0.0211(3) Uani 1 1 d . . .
C24 C 0.63469(12) 0.56101(8) 0.44398(7) 0.0245(3) Uani 1 1 d . . .
H24B H 0.5814 0.5314 0.4590 0.029 Uiso 1 1 calc R . .
C25 C 0.66061(14) 0.56012(9) 0.38248(8) 0.0305(4) Uani 1 1 d . . .
H25B H 0.6235 0.5304 0.3555 0.037 Uiso 1 1 calc R . .
C26 C 0.73930(15) 0.60161(9) 0.35977(7) 0.0336(4) Uani 1 1 d . . .
H26B H 0.7553 0.6011 0.3175 0.040 Uiso 1 1 calc R . .
C27 C 0.79480(14) 0.64410(9) 0.39948(7) 0.0299(3) Uani 1 1 d . . .
H27B H 0.8506 0.6716 0.3846 0.036 Uiso 1 1 calc R . .
C28 C 0.76869(12) 0.64637(8) 0.46110(7) 0.0226(3) Uani 1 1 d . . .
H28B H 0.8065 0.6758 0.4880 0.027 Uiso 1 1 calc R . .
H2N H 0.6850(16) 0.6569(10) 0.5640(9) 0.033(5) Uiso 1 1 d . . .
H2NA H 0.920(2) 0.6003(13) 0.0634(11) 0.054(7) Uiso 1 1 d . . .
H1NA H 0.3229(15) 0.6507(10) -0.0659(9) 0.030(5) Uiso 1 1 d . . .
H1N H 0.0721(16) 0.5961(11) 0.4449(9) 0.035(5) Uiso 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
P1A O1A 1.4780(10) . ?
P1A O3A 1.5985(10) . ?
P1A N3A 1.6264(12) . ?
P1A N1A 1.6394(12) . ?
P2A O2A 1.4756(9) . ?
P2A O4A 1.6124(11) . ?
P2A N4A 1.6327(12) . ?
P2A N2A 1.6374(13) . ?
O3A C5A 1.4040(17) . ?
O4A C17A 1.3996(19) . ?
N1A C11A 1.4122(18) . ?
N1A H1NA 0.91(2) . ?
N2A C23A 1.410(2) . ?
N2A H2NA 0.89(2) . ?
N3A C4A 1.4665(17) . ?
N3A C1A 1.4676(17) . ?
N4A C2A 1.4671(17) . ?
N4A C3A 1.4695(16) . ?
C1A C2A 1.524(2) . ?
C1A H1AA 0.9900 . ?
C1A H1AB 0.9900 . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C3A C4A 1.5290(19) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C5A C10A 1.383(2) . ?
C5A C6A 1.387(2) . ?
C6A C7A 1.386(2) . ?
C6A H6AA 0.9500 . ?
C7A C8A 1.394(3) . ?
C7A H7AA 0.9500 . ?
C8A C9A 1.383(3) . ?
C8A H8AA 0.9500 . ?
C9A C10A 1.396(2) . ?
C9A H9AA 0.9500 . ?
C10A H10A 0.9500 . ?
C11A C12A 1.391(2) . ?
C11A C16A 1.396(2) . ?
C12A C13A 1.389(2) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.389(3) . ?
C13A H13A 0.9500 . ?
C17A C18A 1.388(2) . ?
C17A C22A 1.387(2) . ?
C14A C15A 1.387(2) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.389(2) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
C18A C19A 1.389(2) . ?
C18A H18A 0.9500 . ?
C19A C20A 1.388(3) . ?
C19A H19A 0.9500 . ?
C20A C21A 1.383(3) . ?
C20A H20A 0.9500 . ?
C21A C22A 1.387(2) . ?
C21A H21A 0.9500 . ?
C22A H22A 0.9500 . ?
C23A C24A 1.399(2) . ?
C23A C28A 1.399(2) . ?
C24A C25A 1.393(2) . ?
C24A H24A 0.9500 . ?
C25A C26A 1.388(2) . ?
C25A H25A 0.9500 . ?
C26A C27A 1.391(2) . ?
C26A H26A 0.9500 . ?
C27A C28A 1.383(2) . ?
C27A H27A 0.9500 . ?
C28A H28A 0.9500 . ?
P1 O1 1.4744(9) . ?
P1 O2 1.6064(11) . ?
P1 N3 1.6283(12) . ?
P1 N1 1.6461(13) . ?
P2 O3 1.4707(10) . ?
P2 O4 1.5969(11) . ?
P2 N4 1.6307(13) . ?
P2 N2 1.6443(13) . ?
O2 C5 1.4155(17) . ?
O4 C17 1.4094(17) . ?
N1 C11 1.402(2) . ?
N1 H1N 0.86(2) . ?
N2 C23 1.4157(19) . ?
N2 H2N 0.98(2) . ?
N3 C4 1.4690(17) . ?
N3 C1 1.4718(16) . ?
N4 C2 1.4660(18) . ?
N4 C3 1.4686(17) . ?
C1 C2 1.521(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.527(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.382(2) . ?
C5 C10 1.383(2) . ?
C6 C7 1.393(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.382(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.387(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.387(2) . ?
C9 H9A 0.9500 . ?
C10 H10B 0.9500 . ?
C11 C16 1.405(2) . ?
C11 C12 1.406(2) . ?
C12 C13 1.380(2) . ?
C12 H12B 0.9500 . ?
C13 C14 1.393(2) . ?
C13 H13B 0.9500 . ?
C14 C15 1.394(2) . ?
C14 H14B 0.9500 . ?
C15 C16 1.389(2) . ?
C15 H15B 0.9500 . ?
C16 H16B 0.9500 . ?
C17 C22 1.380(2) . ?
C17 C18 1.382(2) . ?
C18 C19 1.392(2) . ?
C18 H18B 0.9500 . ?
C19 C20 1.380(2) . ?
C19 H19B 0.9500 . ?
C20 C21 1.394(2) . ?
C20 H20B 0.9500 . ?
C21 C22 1.388(2) . ?
C21 H21B 0.9500 . ?
C22 H22B 0.9500 . ?
C23 C28 1.393(2) . ?
C23 C24 1.398(2) . ?
C24 C25 1.390(2) . ?
C24 H24B 0.9500 . ?
C25 C26 1.382(3) . ?
C25 H25B 0.9500 . ?
C26 C27 1.389(3) . ?
C26 H26B 0.9500 . ?
C27 C28 1.393(2) . ?
C27 H27B 0.9500 . ?
C28 H28B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1A P1A O3A 114.64(6) . . ?
O1A P1A N3A 110.61(6) . . ?
O3A P1A N3A 104.36(6) . . ?
O1A P1A N1A 115.93(6) . . ?
O3A P1A N1A 100.57(6) . . ?
N3A P1A N1A 109.77(6) . . ?
O2A P2A O4A 114.02(6) . . ?
O2A P2A N4A 111.03(6) . . ?
O4A P2A N4A 108.44(6) . . ?
O2A P2A N2A 116.53(6) . . ?
O4A P2A N2A 97.31(6) . . ?
N4A P2A N2A 108.53(6) . . ?
C5A O3A P1A 125.27(9) . . ?
C17A O4A P2A 118.59(9) . . ?
C11A N1A P1A 126.33(10) . . ?
C11A N1A H1NA 116.4(12) . . ?
P1A N1A H1NA 115.2(12) . . ?
C23A N2A P2A 124.25(10) . . ?
C23A N2A H2NA 112.7(16) . . ?
P2A N2A H2NA 115.3(16) . . ?
C4A N3A C1A 113.95(11) . . ?
C4A N3A P1A 123.35(9) . . ?
C1A N3A P1A 122.65(9) . . ?
C2A N4A C3A 114.05(11) . . ?
C2A N4A P2A 123.44(9) . . ?
C3A N4A P2A 121.17(9) . . ?
N3A C1A C2A 109.04(11) . . ?
N3A C1A H1AA 109.9 . . ?
C2A C1A H1AA 109.9 . . ?
N3A C1A H1AB 109.9 . . ?
C2A C1A H1AB 109.9 . . ?
H1AA C1A H1AB 108.3 . . ?
N4A C2A C1A 109.27(12) . . ?
N4A C2A H2AA 109.8 . . ?
C1A C2A H2AA 109.8 . . ?
N4A C2A H2AB 109.8 . . ?
C1A C2A H2AB 109.8 . . ?
H2AA C2A H2AB 108.3 . . ?
N4A C3A C4A 108.84(11) . . ?
N4A C3A H3AA 109.9 . . ?
C4A C3A H3AA 109.9 . . ?
N4A C3A H3AB 109.9 . . ?
C4A C3A H3AB 109.9 . . ?
H3AA C3A H3AB 108.3 . . ?
N3A C4A C3A 109.40(11) . . ?
N3A C4A H4AA 109.8 . . ?
C3A C4A H4AA 109.8 . . ?
N3A C4A H4AB 109.8 . . ?
C3A C4A H4AB 109.8 . . ?
H4AA C4A H4AB 108.2 . . ?
C10A C5A C6A 121.63(14) . . ?
C10A C5A O3A 123.08(13) . . ?
C6A C5A O3A 115.23(13) . . ?
C7A C6A C5A 119.16(17) . . ?
C7A C6A H6AA 120.4 . . ?
C5A C6A H6AA 120.4 . . ?
C6A C7A C8A 120.45(17) . . ?
C6A C7A H7AA 119.8 . . ?
C8A C7A H7AA 119.8 . . ?
C9A C8A C7A 119.25(16) . . ?
C9A C8A H8AA 120.4 . . ?
C7A C8A H8AA 120.4 . . ?
C8A C9A C10A 121.22(17) . . ?
C8A C9A H9AA 119.4 . . ?
C10A C9A H9AA 119.4 . . ?
C5A C10A C9A 118.27(15) . . ?
C5A C10A H10A 120.9 . . ?
C9A C10A H10A 120.9 . . ?
C12A C11A C16A 119.22(13) . . ?
C12A C11A N1A 117.96(13) . . ?
C16A C11A N1A 122.83(13) . . ?
C13A C12A C11A 120.57(15) . . ?
C13A C12A H12A 119.7 . . ?
C11A C12A H12A 119.7 . . ?
C14A C13A C12A 120.44(16) . . ?
C14A C13A H13A 119.8 . . ?
C12A C13A H13A 119.8 . . ?
C18A C17A C22A 121.56(15) . . ?
C18A C17A O4A 120.57(13) . . ?
C22A C17A O4A 117.87(14) . . ?
C15A C14A C13A 118.83(15) . . ?
C15A C14A H14A 120.6 . . ?
C13A C14A H14A 120.6 . . ?
C14A C15A C16A 121.32(15) . . ?
C14A C15A H15A 119.3 . . ?
C16A C15A H15A 119.3 . . ?
C15A C16A C11A 119.61(14) . . ?
C15A C16A H16A 120.2 . . ?
C11A C16A H16A 120.2 . . ?
C17A C18A C19A 118.60(15) . . ?
C17A C18A H18A 120.7 . . ?
C19A C18A H18A 120.7 . . ?
C20A C19A C18A 120.58(17) . . ?
C20A C19A H19A 119.7 . . ?
C18A C19A H19A 119.7 . . ?
C21A C20A C19A 119.84(17) . . ?
C21A C20A H20A 120.1 . . ?
C19A C20A H20A 120.1 . . ?
C20A C21A C22A 120.57(15) . . ?
C20A C21A H21A 119.7 . . ?
C22A C21A H21A 119.7 . . ?
C21A C22A C17A 118.83(15) . . ?
C21A C22A H22A 120.6 . . ?
C17A C22A H22A 120.6 . . ?
C24A C23A C28A 119.07(14) . . ?
C24A C23A N2A 122.60(13) . . ?
C28A C23A N2A 118.33(14) . . ?
C25A C24A C23A 119.87(15) . . ?
C25A C24A H24A 120.1 . . ?
C23A C24A H24A 120.1 . . ?
C26A C25A C24A 120.89(15) . . ?
C26A C25A H25A 119.6 . . ?
C24A C25A H25A 119.6 . . ?
C25A C26A C27A 119.01(16) . . ?
C25A C26A H26A 120.5 . . ?
C27A C26A H26A 120.5 . . ?
C28A C27A C26A 120.79(16) . . ?
C28A C27A H27A 119.6 . . ?
C26A C27A H27A 119.6 . . ?
C27A C28A C23A 120.36(15) . . ?
C27A C28A H28A 119.8 . . ?
C23A C28A H28A 119.8 . . ?
O1 P1 O2 113.96(6) . . ?
O1 P1 N3 111.54(6) . . ?
O2 P1 N3 105.54(6) . . ?
O1 P1 N1 116.22(6) . . ?
O2 P1 N1 101.38(6) . . ?
N3 P1 N1 107.19(6) . . ?
O3 P2 O4 114.16(6) . . ?
O3 P2 N4 112.19(6) . . ?
O4 P2 N4 104.67(6) . . ?
O3 P2 N2 115.65(7) . . ?
O4 P2 N2 101.65(7) . . ?
N4 P2 N2 107.42(6) . . ?
C5 O2 P1 120.92(9) . . ?
C17 O4 P2 123.40(9) . . ?
C11 N1 P1 125.29(10) . . ?
C11 N1 H1N 112.1(14) . . ?
P1 N1 H1N 118.1(14) . . ?
C23 N2 P2 125.50(11) . . ?
C23 N2 H2N 113.5(12) . . ?
P2 N2 H2N 115.5(12) . . ?
C4 N3 C1 113.55(11) . . ?
C4 N3 P1 121.33(9) . . ?
C1 N3 P1 122.21(9) . . ?
C2 N4 C3 112.83(11) . . ?
C2 N4 P2 122.46(9) . . ?
C3 N4 P2 121.69(10) . . ?
N3 C1 C2 109.56(11) . . ?
N3 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
N3 C1 H1B 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
N4 C2 C1 109.02(11) . . ?
N4 C2 H2A 109.9 . . ?
C1 C2 H2A 109.9 . . ?
N4 C2 H2B 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
N4 C3 C4 108.83(12) . . ?
N4 C3 H3A 109.9 . . ?
C4 C3 H3A 109.9 . . ?
N4 C3 H3B 109.9 . . ?
C4 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
N3 C4 C3 108.52(12) . . ?
N3 C4 H4A 110.0 . . ?
C3 C4 H4A 110.0 . . ?
N3 C4 H4B 110.0 . . ?
C3 C4 H4B 110.0 . . ?
H4A C4 H4B 108.4 . . ?
C6 C5 C10 121.88(14) . . ?
C6 C5 O2 118.33(13) . . ?
C10 C5 O2 119.75(13) . . ?
C5 C6 C7 118.84(15) . . ?
C5 C6 H6A 120.6 . . ?
C7 C6 H6A 120.6 . . ?
C8 C7 C6 120.29(15) . . ?
C8 C7 H7A 119.9 . . ?
C6 C7 H7A 119.9 . . ?
C7 C8 C9 119.64(15) . . ?
C7 C8 H8A 120.2 . . ?
C9 C8 H8A 120.2 . . ?
C10 C9 C8 120.98(15) . . ?
C10 C9 H9A 119.5 . . ?
C8 C9 H9A 119.5 . . ?
C5 C10 C9 118.33(14) . . ?
C5 C10 H10B 120.8 . . ?
C9 C10 H10B 120.8 . . ?
N1 C11 C16 122.67(13) . . ?
N1 C11 C12 118.75(13) . . ?
C16 C11 C12 118.57(14) . . ?
C13 C12 C11 120.58(15) . . ?
C13 C12 H12B 119.7 . . ?
C11 C12 H12B 119.7 . . ?
C12 C13 C14 120.73(15) . . ?
C12 C13 H13B 119.6 . . ?
C14 C13 H13B 119.6 . . ?
C13 C14 C15 119.23(15) . . ?
C13 C14 H14B 120.4 . . ?
C15 C14 H14B 120.4 . . ?
C16 C15 C14 120.55(15) . . ?
C16 C15 H15B 119.7 . . ?
C14 C15 H15B 119.7 . . ?
C15 C16 C11 120.33(14) . . ?
C15 C16 H16B 119.8 . . ?
C11 C16 H16B 119.8 . . ?
C22 C17 C18 121.64(13) . . ?
C22 C17 O4 120.39(13) . . ?
C18 C17 O4 117.77(14) . . ?
C17 C18 C19 118.70(14) . . ?
C17 C18 H18B 120.6 . . ?
C19 C18 H18B 120.6 . . ?
C20 C19 C18 120.74(14) . . ?
C20 C19 H19B 119.6 . . ?
C18 C19 H19B 119.6 . . ?
C19 C20 C21 119.57(14) . . ?
C19 C20 H20B 120.2 . . ?
C21 C20 H20B 120.2 . . ?
C22 C21 C20 120.31(15) . . ?
C22 C21 H21B 119.8 . . ?
C20 C21 H21B 119.8 . . ?
C17 C22 C21 119.02(14) . . ?
C17 C22 H22B 120.5 . . ?
C21 C22 H22B 120.5 . . ?
C28 C23 C24 119.18(14) . . ?
C28 C23 N2 118.13(13) . . ?
C24 C23 N2 122.68(14) . . ?
C25 C24 C23 119.51(15) . . ?
C25 C24 H24B 120.2 . . ?
C23 C24 H24B 120.2 . . ?
C26 C25 C24 121.35(16) . . ?
C26 C25 H25B 119.3 . . ?
C24 C25 H25B 119.3 . . ?
C25 C26 C27 119.25(15) . . ?
C25 C26 H26B 120.4 . . ?
C27 C26 H26B 120.4 . . ?
C26 C27 C28 120.04(16) . . ?
C26 C27 H27B 120.0 . . ?
C28 C27 H27B 120.0 . . ?
C23 C28 C27 120.59(15) . . ?
C23 C28 H28B 119.7 . . ?
C27 C28 H28B 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1A P1A O3A C5A 62.37(12) . . . . ?
N3A P1A O3A C5A -176.48(10) . . . . ?
N1A P1A O3A C5A -62.72(11) . . . . ?
O2A P2A O4A C17A 78.22(11) . . . . ?
N4A P2A O4A C17A -46.03(11) . . . . ?
N2A P2A O4A C17A -158.40(10) . . . . ?
O1A P1A N1A C11A 57.98(13) . . . . ?
O3A P1A N1A C11A -177.81(11) . . . . ?
N3A P1A N1A C11A -68.23(13) . . . . ?
O2A P2A N2A C23A -68.81(13) . . . . ?
O4A P2A N2A C23A 169.68(12) . . . . ?
N4A P2A N2A C23A 57.38(13) . . . . ?
O1A P1A N3A C4A 13.31(13) . . . . ?
O3A P1A N3A C4A -110.47(11) . . . . ?
N1A P1A N3A C4A 142.48(11) . . . . ?
O1A P1A N3A C1A -169.63(11) . . . . ?
O3A P1A N3A C1A 66.59(13) . . . . ?
N1A P1A N3A C1A -40.46(13) . . . . ?
O2A P2A N4A C2A -18.36(14) . . . . ?
O4A P2A N4A C2A 107.64(12) . . . . ?
N2A P2A N4A C2A -147.69(12) . . . . ?
O2A P2A N4A C3A 175.68(11) . . . . ?
O4A P2A N4A C3A -58.32(12) . . . . ?
N2A P2A N4A C3A 46.35(13) . . . . ?
C4A N3A C1A C2A -57.71(16) . . . . ?
P1A N3A C1A C2A 124.97(12) . . . . ?
C3A N4A C2A C1A -57.89(15) . . . . ?
P2A N4A C2A C1A 135.25(11) . . . . ?
N3A C1A C2A N4A 55.00(15) . . . . ?
C2A N4A C3A C4A 57.47(15) . . . . ?
P2A N4A C3A C4A -135.34(11) . . . . ?
C1A N3A C4A C3A 57.73(15) . . . . ?
P1A N3A C4A C3A -124.98(11) . . . . ?
N4A C3A C4A N3A -54.65(14) . . . . ?
P1A O3A C5A C10A -20.05(19) . . . . ?
P1A O3A C5A C6A 162.47(12) . . . . ?
C10A C5A C6A C7A 1.1(3) . . . . ?
O3A C5A C6A C7A 178.62(16) . . . . ?
C5A C6A C7A C8A 0.0(3) . . . . ?
C6A C7A C8A C9A -1.0(3) . . . . ?
C7A C8A C9A C10A 0.9(3) . . . . ?
C6A C5A C10A C9A -1.2(2) . . . . ?
O3A C5A C10A C9A -178.49(14) . . . . ?
C8A C9A C10A C5A 0.1(3) . . . . ?
P1A N1A C11A C12A 178.66(11) . . . . ?
P1A N1A C11A C16A -1.6(2) . . . . ?
C16A C11A C12A C13A -0.1(2) . . . . ?
N1A C11A C12A C13A 179.64(14) . . . . ?
C11A C12A C13A C14A 1.1(2) . . . . ?
P2A O4A C17A C18A -59.95(16) . . . . ?
P2A O4A C17A C22A 121.18(12) . . . . ?
C12A C13A C14A C15A -1.2(3) . . . . ?
C13A C14A C15A C16A 0.4(3) . . . . ?
C14A C15A C16A C11A 0.5(2) . . . . ?
C12A C11A C16A C15A -0.6(2) . . . . ?
N1A C11A C16A C15A 179.60(13) . . . . ?
C22A C17A C18A C19A -1.5(2) . . . . ?
O4A C17A C18A C19A 179.67(14) . . . . ?
C17A C18A C19A C20A 0.5(3) . . . . ?
C18A C19A C20A C21A 0.6(3) . . . . ?
C19A C20A C21A C22A -0.7(3) . . . . ?
C20A C21A C22A C17A -0.2(2) . . . . ?
C18A C17A C22A C21A 1.4(2) . . . . ?
O4A C17A C22A C21A -179.76(13) . . . . ?
P2A N2A C23A C24A 16.3(2) . . . . ?
P2A N2A C23A C28A -164.35(11) . . . . ?
C28A C23A C24A C25A 0.5(2) . . . . ?
N2A C23A C24A C25A 179.86(13) . . . . ?
C23A C24A C25A C26A -0.3(2) . . . . ?
C24A C25A C26A C27A -0.3(2) . . . . ?
C25A C26A C27A C28A 0.5(2) . . . . ?
C26A C27A C28A C23A -0.3(2) . . . . ?
C24A C23A C28A C27A -0.2(2) . . . . ?
N2A C23A C28A C27A -179.62(14) . . . . ?
O1 P1 O2 C5 -42.93(12) . . . . ?
N3 P1 O2 C5 -165.65(10) . . . . ?
N1 P1 O2 C5 82.71(11) . . . . ?
O3 P2 O4 C17 47.47(13) . . . . ?
N4 P2 O4 C17 170.52(11) . . . . ?
N2 P2 O4 C17 -77.77(12) . . . . ?
O1 P1 N1 C11 -63.47(13) . . . . ?
O2 P1 N1 C11 172.41(11) . . . . ?
N3 P1 N1 C11 62.03(13) . . . . ?
O3 P2 N2 C23 68.06(14) . . . . ?
O4 P2 N2 C23 -167.70(12) . . . . ?
N4 P2 N2 C23 -58.09(14) . . . . ?
O1 P1 N3 C4 -27.23(13) . . . . ?
O2 P1 N3 C4 97.03(12) . . . . ?
N1 P1 N3 C4 -155.50(11) . . . . ?
O1 P1 N3 C1 173.32(11) . . . . ?
O2 P1 N3 C1 -62.42(13) . . . . ?
N1 P1 N3 C1 45.05(13) . . . . ?
O3 P2 N4 C2 29.43(14) . . . . ?
O4 P2 N4 C2 -94.88(12) . . . . ?
N2 P2 N4 C2 157.60(12) . . . . ?
O3 P2 N4 C3 -171.63(11) . . . . ?
O4 P2 N4 C3 64.05(13) . . . . ?
N2 P2 N4 C3 -43.46(14) . . . . ?
C4 N3 C1 C2 57.20(16) . . . . ?
P1 N3 C1 C2 -141.89(11) . . . . ?
C3 N4 C2 C1 58.95(15) . . . . ?
P2 N4 C2 C1 -140.43(11) . . . . ?
N3 C1 C2 N4 -55.05(15) . . . . ?
C2 N4 C3 C4 -60.13(16) . . . . ?
P2 N4 C3 C4 139.09(11) . . . . ?
C1 N3 C4 C3 -57.89(15) . . . . ?
P1 N3 C4 C3 141.01(11) . . . . ?
N4 C3 C4 N3 56.98(16) . . . . ?
P1 O2 C5 C6 82.03(16) . . . . ?
P1 O2 C5 C10 -100.34(14) . . . . ?
C10 C5 C6 C7 1.8(2) . . . . ?
O2 C5 C6 C7 179.34(14) . . . . ?
C5 C6 C7 C8 -2.1(2) . . . . ?
C6 C7 C8 C9 0.9(2) . . . . ?
C7 C8 C9 C10 0.7(2) . . . . ?
C6 C5 C10 C9 -0.2(2) . . . . ?
O2 C5 C10 C9 -177.75(14) . . . . ?
C8 C9 C10 C5 -1.1(2) . . . . ?
P1 N1 C11 C16 10.9(2) . . . . ?
P1 N1 C11 C12 -170.44(11) . . . . ?
N1 C11 C12 C13 -179.11(13) . . . . ?
C16 C11 C12 C13 -0.4(2) . . . . ?
C11 C12 C13 C14 0.8(2) . . . . ?
C12 C13 C14 C15 -0.7(2) . . . . ?
C13 C14 C15 C16 0.3(2) . . . . ?
C14 C15 C16 C11 0.1(2) . . . . ?
N1 C11 C16 C15 178.59(13) . . . . ?
C12 C11 C16 C15 0.0(2) . . . . ?
P2 O4 C17 C22 88.57(15) . . . . ?
P2 O4 C17 C18 -96.48(14) . . . . ?
C22 C17 C18 C19 1.5(2) . . . . ?
O4 C17 C18 C19 -173.41(13) . . . . ?
C17 C18 C19 C20 -0.4(2) . . . . ?
C18 C19 C20 C21 -0.6(2) . . . . ?
C19 C20 C21 C22 0.5(2) . . . . ?
C18 C17 C22 C21 -1.6(2) . . . . ?
O4 C17 C22 C21 173.16(13) . . . . ?
C20 C21 C22 C17 0.6(2) . . . . ?
P2 N2 C23 C28 172.80(11) . . . . ?
P2 N2 C23 C24 -5.8(2) . . . . ?
C28 C23 C24 C25 -2.9(2) . . . . ?
N2 C23 C24 C25 175.61(14) . . . . ?
C23 C24 C25 C26 1.4(2) . . . . ?
C24 C25 C26 C27 1.2(3) . . . . ?
C25 C26 C27 C28 -2.1(3) . . . . ?
C24 C23 C28 C27 2.0(2) . . . . ?
N2 C23 C28 C27 -176.63(14) . . . . ?
C26 C27 C28 C23 0.6(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
_geom_hbond_publ_flag
N1 H1N O1A 0.86(2) 1.98(2) 2.8282(17) 169(2) 2_565 ?
N2 H2N O1 0.98(2) 1.931(19) 2.8770(16) 162.6(18) 4_566 ?
N2A H2NA O3 0.89(2) 1.98(2) 2.8558(16) 166(2) 2_664 ?
N1A H1NA O2A 0.914(19) 1.941(19) 2.8174(15) 160.2(17) 4_465 ?


_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        29.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.046

