# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_kiev96
_database_code_depnum_ccdc_archive 'CCDC 1984336'
loop_
_audit_author_name
_audit_author_address
'Viktoriya Dyakonenko'
;SSI Institute for Single Crystals National Academy of Sciences of Ukraine
Ukraine
;
_audit_update_record             
;
2020-02-16 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;
_audit_creation_date             2020-02-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C11 H19 N5 O8 P2'
_chemical_formula_sum            'C11 H19 N5 O8 P2'
_chemical_formula_weight         411.25
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   8.9985(2)
_cell_length_b                   11.8275(3)
_cell_length_c                   17.5639(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.400(2)
_cell_angle_gamma                90
_cell_volume                     1818.43(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13095
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.0112
_cell_measurement_theta_min      2.8426
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.893
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET)
(compiled Jan  8 2009,16:24:04)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            30070
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_min         2.895
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.1827
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -100.00   44.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.2351    0.0000  240.0000 144

#__ type_ start__ end____ width___ exp.time_
  2 omega  -74.00   -3.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.2351  100.0000  271.0000 71

#__ type_ start__ end____ width___ exp.time_
  3 omega  -96.00    5.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.2351  -77.0000   60.0000 101

#__ type_ start__ end____ width___ exp.time_
  4 omega   57.00  109.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       29.4851  179.0000  270.0000 52

#__ type_ start__ end____ width___ exp.time_
  5 omega  -25.00   24.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       29.4851  -99.0000  268.0000 49

#__ type_ start__ end____ width___ exp.time_
  6 omega   56.00  109.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       29.4851  179.0000   90.0000 53

#__ type_ start__ end____ width___ exp.time_
  7 omega -101.00    5.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.2351  -77.0000  180.0000 106

#__ type_ start__ end____ width___ exp.time_
  8 omega -101.00    5.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.2351  -77.0000  270.0000 106

#__ type_ start__ end____ width___ exp.time_
  9 omega  -24.00   75.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       29.4851 -100.0000   88.0000 99
;
_diffrn_measurement_device_type  'Goniometer KM4/Xcalibur, detector: Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0390291796
_diffrn_orient_matrix_UB_12      0.0044565309
_diffrn_orient_matrix_UB_13      0.0306344881
_diffrn_orient_matrix_UB_21      0.0658171781
_diffrn_orient_matrix_UB_22      0.0246835784
_diffrn_orient_matrix_UB_23      0.0245530211
_diffrn_orient_matrix_UB_31      -0.0265806854
_diffrn_orient_matrix_UB_32      0.0544358651
_diffrn_orient_matrix_UB_33      -0.0136079684
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3911
_reflns_number_total             5285
_reflns_odcompleteness_completeness 93.29
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.03
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET)
(compiled Jan  8 2009,16:24:04)
;
_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET)
(compiled Jan  8 2009,16:24:04)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET)
(compiled Jan  8 2009,16:24:04)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.729
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         5285
_refine_ls_number_restraints     32
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0498
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0737P)²+0.4322P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1378
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 P1-O1A
 1.58 with sigma of 0.001
 P1-O1B
 1.58 with sigma of 0.001
 O1A-C1A
 1.43 with sigma of 0.001
 O1B-C1B
 1.43 with sigma of 0.001
 P1-O2A
 1.58 with sigma of 0.001
 P1-O2B
 1.58 with sigma of 0.001
 O2A-C2A
 1.43 with sigma of 0.001
 O2B-C2B
 1.43 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
O2A \\sim C2A: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
O1A \\sim C1A: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
O2B \\sim C2B: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
O1B \\sim C1B: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
4. Others
 Fixed Sof: O1A(0.7) O2A(0.7) C1A(0.7) H1AA(0.7) H1AB(0.7) H1AC(0.7) C2A(0.7)
 H2AA(0.7) H2AB(0.7) H2AC(0.7) O1B(0.3) O2B(0.3) C1B(0.3) H1BA(0.3) H1BB(0.3)
 H1BC(0.3) C2B(0.3) H2BA(0.3) H2BB(0.3) H2BC(0.3)
5.a Idealised Me refined as rotating group:
 C1A(H1AA,H1AB,H1AC), C2A(H2AA,H2AB,H2AC), C10(H10A,H10B,H10C), C11(H11A,H11B,
 H11C), C1B(H1BA,H1BB,H1BC), C2B(H2BA,H2BB,H2BC)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 -0.07932(6) 0.40565(5) 0.62610(3) 0.04332(15) Uani 1 1 d D . . . .
P2 P 0.21299(5) 0.40243(4) 0.98403(3) 0.03119(12) Uani 1 1 d . . . . .
O1A O 0.0162(3) 0.51903(14) 0.63174(19) 0.0617(7) Uani 0.7 1 d D U P A 1
O2A O -0.1497(2) 0.4222(2) 0.69944(9) 0.0516(6) Uani 0.7 1 d D U P A 1
O3 O -0.18266(17) 0.38894(15) 0.54989(9) 0.0523(4) Uani 1 1 d . . . . .
O4 O 0.16269(17) 0.34101(13) 0.76946(8) 0.0474(4) Uani 1 1 d . . . . .
O5 O 0.4649(2) 0.26994(17) 1.06684(8) 0.0642(5) Uani 1 1 d . . . . .
O6 O 0.31864(17) 0.49853(14) 1.02741(10) 0.0513(4) Uani 1 1 d . . . . .
O7 O 0.10296(16) 0.45504(12) 0.91200(8) 0.0406(3) Uani 1 1 d . . . . .
O8 O 0.12737(18) 0.34226(13) 1.03242(9) 0.0472(4) Uani 1 1 d . . . . .
N1 N 0.0603(2) 0.31500(15) 0.63964(9) 0.0386(4) Uani 1 1 d . . . . .
H1 H 0.069(3) 0.286(2) 0.6045(18) 0.064(9) Uiso 1 1 d . . . . .
N2 N 0.2825(2) 0.22580(16) 0.69864(9) 0.0431(4) Uani 1 1 d . . . . .
H2 H 0.286(3) 0.211(2) 0.6563(18) 0.067(8) Uiso 1 1 d . . . . .
N3 N 0.40762(17) 0.20661(14) 0.83059(8) 0.0346(3) Uani 1 1 d . . . . .
N4 N 0.5254(2) 0.18706(17) 0.96313(9) 0.0443(4) Uani 1 1 d . . . . .
H4 H 0.596(3) 0.160(2) 0.9951(16) 0.057(7) Uiso 1 1 d . . . . .
N5 N 0.33001(18) 0.32319(14) 0.94671(9) 0.0342(3) Uani 1 1 d . . . . .
H5 H 0.316(3) 0.312(2) 0.9013(16) 0.055(7) Uiso 1 1 d . . . . .
C1A C -0.0489(15) 0.6275(6) 0.6087(7) 0.099(4) Uani 0.7 1 d D U P A 1
H1AA H 0.028899 0.677392 0.599087 0.149 Uiso 0.7 1 calc GR . P A 1
H1AB H -0.091112 0.658073 0.649799 0.149 Uiso 0.7 1 calc GR . P A 1
H1AC H -0.128201 0.620000 0.561924 0.149 Uiso 0.7 1 calc GR . P A 1
C2A C -0.2448(7) 0.3309(4) 0.7126(4) 0.0839(18) Uani 0.7 1 d D U P A 1
H2AA H -0.333228 0.360616 0.727523 0.126 Uiso 0.7 1 calc GR . P A 1
H2AB H -0.188785 0.283385 0.753596 0.126 Uiso 0.7 1 calc GR . P A 1
H2AC H -0.276425 0.287523 0.665402 0.126 Uiso 0.7 1 calc GR . P A 1
C3 C 0.1698(2) 0.29713(15) 0.70864(9) 0.0312(3) Uani 1 1 d . . . . .
C4 C 0.4002(2) 0.17996(16) 0.75614(10) 0.0336(4) Uani 1 1 d . . . . .
C5 C 0.5017(3) 0.10706(19) 0.73331(11) 0.0443(5) Uani 1 1 d . . . . .
H5A H 0.491(3) 0.093(2) 0.6805(17) 0.056(7) Uiso 1 1 d . . . . .
C6 C 0.6147(3) 0.0594(2) 0.79057(13) 0.0522(6) Uani 1 1 d . . . . .
H6 H 0.692(3) 0.011(2) 0.7746(16) 0.062(8) Uiso 1 1 d . . . . .
C7 C 0.6233(2) 0.0840(2) 0.86869(12) 0.0477(5) Uani 1 1 d . . . . .
H7 H 0.690(3) 0.054(3) 0.9096(18) 0.070(8) Uiso 1 1 d . . . . .
C8 C 0.5173(2) 0.15875(16) 0.88523(10) 0.0344(4) Uani 1 1 d . . . . .
C9 C 0.4408(2) 0.26065(18) 0.99549(10) 0.0408(4) Uani 1 1 d . . . . .
C10 C 0.2627(3) 0.5761(2) 1.07724(18) 0.0670(7) Uani 1 1 d . . . . .
H10A H 0.347420 0.611522 1.112514 0.100 Uiso 1 1 calc GR . . . .
H10B H 0.202223 0.535811 1.106707 0.100 Uiso 1 1 calc GR . . . .
H10C H 0.201000 0.632877 1.045787 0.100 Uiso 1 1 calc GR . . . .
C11 C 0.1452(4) 0.5472(2) 0.86802(15) 0.0640(7) Uani 1 1 d . . . . .
H11A H 0.247786 0.536168 0.862307 0.096 Uiso 1 1 calc GR . . . .
H11B H 0.139405 0.616965 0.895140 0.096 Uiso 1 1 calc GR . . . .
H11C H 0.076760 0.550111 0.817239 0.096 Uiso 1 1 calc GR . . . .
O1B O -0.0518(8) 0.5258(2) 0.6656(3) 0.0636(18) Uani 0.3 1 d D U P A 2
O2B O -0.1532(5) 0.3393(5) 0.6864(3) 0.0623(17) Uani 0.3 1 d D U P A 2
C1B C -0.045(3) 0.6073(14) 0.6064(10) 0.075(5) Uani 0.3 1 d D U P A 2
H1BA H 0.011471 0.672269 0.629940 0.112 Uiso 0.3 1 calc GR . P A 2
H1BB H -0.146708 0.629812 0.580591 0.112 Uiso 0.3 1 calc GR . P A 2
H1BC H 0.004827 0.574647 0.568867 0.112 Uiso 0.3 1 calc GR . P A 2
C2B C -0.2867(11) 0.3782(9) 0.7095(9) 0.068(4) Uani 0.3 1 d D U P A 2
H2BA H -0.375816 0.345509 0.675844 0.101 Uiso 0.3 1 calc GR . P A 2
H2BB H -0.292360 0.459064 0.705482 0.101 Uiso 0.3 1 calc GR . P A 2
H2BC H -0.281524 0.355958 0.762595 0.101 Uiso 0.3 1 calc GR . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1A 1.5836(10) . ?
P1 O2A 1.5736(10) . ?
P1 O3 1.4555(14) . ?
P1 N1 1.6264(18) . ?
P1 O1B 1.5760(10) . ?
P1 O2B 1.5824(10) . ?
P2 O6 1.5623(16) . ?
P2 O7 1.5453(14) . ?
P2 O8 1.4580(15) . ?
P2 N5 1.6544(16) . ?
O1A C1A 1.4296(10) . ?
O2A C2A 1.4295(10) . ?
O4 C3 1.203(2) . ?
O5 C9 1.226(2) . ?
O6 C10 1.437(3) . ?
O7 C11 1.437(3) . ?
N1 H1 0.73(3) . ?
N1 C3 1.390(2) . ?
N2 H2 0.77(3) . ?
N2 C3 1.361(2) . ?
N2 C4 1.393(2) . ?
N3 C4 1.332(2) . ?
N3 C8 1.333(2) . ?
N4 H4 0.81(3) . ?
N4 C8 1.394(2) . ?
N4 C9 1.364(3) . ?
N5 H5 0.79(3) . ?
N5 C9 1.371(2) . ?
C1A H1AA 0.9600 . ?
C1A H1AB 0.9600 . ?
C1A H1AC 0.9600 . ?
C2A H2AA 0.9600 . ?
C2A H2AB 0.9600 . ?
C2A H2AC 0.9600 . ?
C4 C5 1.382(3) . ?
C5 H5A 0.93(3) . ?
C5 C6 1.374(3) . ?
C6 H6 0.99(3) . ?
C6 C7 1.387(3) . ?
C7 H7 0.90(3) . ?
C7 C8 1.380(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
O1B C1B 1.4300(10) . ?
O2B C2B 1.4297(10) . ?
C1B H1BA 0.9600 . ?
C1B H1BB 0.9600 . ?
C1B H1BC 0.9600 . ?
C2B H2BA 0.9600 . ?
C2B H2BB 0.9600 . ?
C2B H2BC 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1A P1 N1 99.17(12) . . ?
O2A P1 O1A 99.15(16) . . ?
O2A P1 N1 113.95(11) . . ?
O3 P1 O1A 113.23(13) . . ?
O3 P1 O2A 118.51(11) . . ?
O3 P1 N1 110.61(9) . . ?
O3 P1 O1B 122.0(2) . . ?
O3 P1 O2B 105.7(2) . . ?
O1B P1 N1 119.5(2) . . ?
O1B P1 O2B 101.5(4) . . ?
O2B P1 N1 90.31(19) . . ?
O6 P2 N5 103.54(8) . . ?
O7 P2 O6 107.95(9) . . ?
O7 P2 N5 104.45(8) . . ?
O8 P2 O6 114.51(9) . . ?
O8 P2 O7 110.42(9) . . ?
O8 P2 N5 115.18(9) . . ?
C1A O1A P1 124.1(6) . . ?
C2A O2A P1 114.1(3) . . ?
C10 O6 P2 120.13(16) . . ?
C11 O7 P2 123.11(16) . . ?
P1 N1 H1 115(2) . . ?
C3 N1 P1 126.55(14) . . ?
C3 N1 H1 118(2) . . ?
C3 N2 H2 117(2) . . ?
C3 N2 C4 127.69(15) . . ?
C4 N2 H2 115(2) . . ?
C4 N3 C8 117.83(15) . . ?
C8 N4 H4 116.0(19) . . ?
C9 N4 H4 112.8(19) . . ?
C9 N4 C8 130.92(16) . . ?
P2 N5 H5 122.1(19) . . ?
C9 N5 P2 119.70(13) . . ?
C9 N5 H5 117.4(19) . . ?
O1A C1A H1AA 109.5 . . ?
O1A C1A H1AB 109.5 . . ?
O1A C1A H1AC 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
O2A C2A H2AA 109.5 . . ?
O2A C2A H2AB 109.5 . . ?
O2A C2A H2AC 109.5 . . ?
H2AA C2A H2AB 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 109.5 . . ?
O4 C3 N1 122.38(17) . . ?
O4 C3 N2 125.23(16) . . ?
N2 C3 N1 112.38(15) . . ?
N3 C4 N2 118.47(16) . . ?
N3 C4 C5 123.13(16) . . ?
C5 C4 N2 118.38(15) . . ?
C4 C5 H5A 119.1(16) . . ?
C6 C5 C4 118.06(17) . . ?
C6 C5 H5A 122.9(16) . . ?
C5 C6 H6 118.5(16) . . ?
C5 C6 C7 120.00(19) . . ?
C7 C6 H6 121.4(16) . . ?
C6 C7 H7 125.6(19) . . ?
C8 C7 C6 117.38(18) . . ?
C8 C7 H7 117.0(19) . . ?
N3 C8 N4 117.79(16) . . ?
N3 C8 C7 123.58(16) . . ?
C7 C8 N4 118.63(16) . . ?
O5 C9 N4 119.97(18) . . ?
O5 C9 N5 121.41(18) . . ?
N4 C9 N5 118.62(16) . . ?
O6 C10 H10A 109.5 . . ?
O6 C10 H10B 109.5 . . ?
O6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O7 C11 H11A 109.5 . . ?
O7 C11 H11B 109.5 . . ?
O7 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1B O1B P1 108.4(10) . . ?
C2B O2B P1 122.8(6) . . ?
O1B C1B H1BA 109.5 . . ?
O1B C1B H1BB 109.5 . . ?
O1B C1B H1BC 109.5 . . ?
H1BA C1B H1BB 109.5 . . ?
H1BA C1B H1BC 109.5 . . ?
H1BB C1B H1BC 109.5 . . ?
O2B C2B H2BA 109.5 . . ?
O2B C2B H2BB 109.5 . . ?
O2B C2B H2BC 109.5 . . ?
H2BA C2B H2BB 109.5 . . ?
H2BA C2B H2BC 109.5 . . ?
H2BB C2B H2BC 109.5 . . ?

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
_geom_hbond_publ_flag
N1 H1 O8 0.73(3) 2.12(3) 2.810(2) 160(3) 4_565 yes
N2 H2 O8 0.77(3) 2.39(3) 3.038(2) 142(3) 4_565 yes
N4 H4 O3 0.81(3) 2.08(3) 2.859(2) 160(3) 4_666 yes
N5 H5 N3 0.79(3) 2.06(3) 2.685(2) 136(2) . yes

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
P1 N1 C3 O4 7.8(3) . . . . ?
P1 N1 C3 N2 -172.18(16) . . . . ?
P2 N5 C9 O5 -6.9(3) . . . . ?
P2 N5 C9 N4 173.23(16) . . . . ?
O1A P1 O2A C2A -179.4(4) . . . . ?
O1A P1 N1 C3 68.9(2) . . . . ?
O2A P1 O1A C1A -76.8(7) . . . . ?
O2A P1 N1 C3 -35.5(2) . . . . ?
O3 P1 O1A C1A 49.7(7) . . . . ?
O3 P1 O2A C2A 57.8(4) . . . . ?
O3 P1 N1 C3 -171.95(17) . . . . ?
O3 P1 O1B C1B -39.7(11) . . . . ?
O3 P1 O2B C2B -72.7(9) . . . . ?
O6 P2 O7 C11 33.40(18) . . . . ?
O6 P2 N5 C9 69.16(18) . . . . ?
O7 P2 O6 C10 78.7(2) . . . . ?
O7 P2 N5 C9 -177.91(16) . . . . ?
O8 P2 O6 C10 -44.8(2) . . . . ?
O8 P2 O7 C11 159.28(16) . . . . ?
O8 P2 N5 C9 -56.63(19) . . . . ?
N1 P1 O1A C1A 166.9(7) . . . . ?
N1 P1 O2A C2A -75.0(4) . . . . ?
N1 P1 O1B C1B 106.4(11) . . . . ?
N1 P1 O2B C2B 175.8(9) . . . . ?
N2 C4 C5 C6 -178.0(2) . . . . ?
N3 C4 C5 C6 0.6(4) . . . . ?
N5 P2 O6 C10 -170.98(19) . . . . ?
N5 P2 O7 C11 -76.33(17) . . . . ?
C3 N2 C4 N3 0.1(3) . . . . ?
C3 N2 C4 C5 178.8(2) . . . . ?
C4 N2 C3 O4 7.6(4) . . . . ?
C4 N2 C3 N1 -172.4(2) . . . . ?
C4 N3 C8 N4 179.75(19) . . . . ?
C4 N3 C8 C7 0.3(3) . . . . ?
C4 C5 C6 C7 0.7(4) . . . . ?
C5 C6 C7 C8 -1.4(4) . . . . ?
C6 C7 C8 N3 0.9(4) . . . . ?
C6 C7 C8 N4 -178.5(2) . . . . ?
C8 N3 C4 N2 177.50(18) . . . . ?
C8 N3 C4 C5 -1.1(3) . . . . ?
C8 N4 C9 O5 177.7(2) . . . . ?
C8 N4 C9 N5 -2.4(4) . . . . ?
C9 N4 C8 N3 -2.3(4) . . . . ?
C9 N4 C8 C7 177.2(2) . . . . ?
O1B P1 N1 C3 38.4(4) . . . . ?
O1B P1 O2B C2B 55.5(9) . . . . ?
O2B P1 N1 C3 -65.1(3) . . . . ?
O2B P1 O1B C1B -156.6(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_kiev327
_database_code_depnum_ccdc_archive 'CCDC 1984339'
loop_
_audit_author_name
_audit_author_address
'Viktoriya Dyakonenko'
;SSI Institute for Single Crystals National Academy of Sciences of Ukraine
Ukraine
;
_audit_update_record             
;
2020-02-28 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;
_audit_creation_date             2020-02-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H36 Eu N11 O19 P4, C3 H8 O'
_chemical_formula_sum            'C25 H44 Eu N11 O20 P4'
_chemical_formula_weight         1094.55
_chemical_melting_point          ?
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'
Eu Eu -0.1578 3.6682 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.3844(6)
_cell_length_b                   17.2947(6)
_cell_length_c                   19.5123(8)
_cell_angle_alpha                90
_cell_angle_beta                 106.525(5)
_cell_angle_gamma                90
_cell_volume                     4330.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3024
_cell_measurement_temperature    294
_cell_measurement_theta_max      23.4000
_cell_measurement_theta_min      3.2750
_shelx_estimated_absorpt_T_max   0.632
_shelx_estimated_absorpt_T_min   0.432
_exptl_absorpt_coefficient_mu    1.683
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46299
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2216
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0733
_diffrn_reflns_av_unetI/netI     0.0819
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25701
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         3.200
_diffrn_ambient_temperature      294
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1827
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -22.00  69.00   1.00   20.00    --   27.65 -99.00 150.00   91
  2  ω      0.00  98.00   1.00   20.00    --   27.65  77.00 -30.00   98
  3  ω     39.00  68.00   1.00   20.00    --   27.65 -99.00   0.00   29
  4  ω    -35.00  55.00   1.00   20.00    --   27.65 -77.00-150.00   90
  5  ω    -28.00  10.00   1.00   20.00    --   27.65 -77.00  60.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0408235000
_diffrn_orient_matrix_UB_12      -0.0123603000
_diffrn_orient_matrix_UB_13      0.0139595000
_diffrn_orient_matrix_UB_21      0.0362512000
_diffrn_orient_matrix_UB_22      -0.0215584000
_diffrn_orient_matrix_UB_23      0.0267467000
_diffrn_orient_matrix_UB_31      0.0085473000
_diffrn_orient_matrix_UB_32      0.0326323000
_diffrn_orient_matrix_UB_33      0.0229791000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5974
_reflns_number_total             8470
_reflns_odcompleteness_completeness 87.19
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.79
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.450
_refine_diff_density_min         -0.973
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     560
_refine_ls_number_reflns         8470
_refine_ls_number_restraints     28
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0591
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0728P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1413
_refine_ls_wR_factor_ref         0.1622
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C24-C23 = C25-C23
 1.45 with sigma of 0.002
 O9-C12 = O10-C13 = O14-C21 = O15-C22 = O7-C11 = O6-C10 = O1-C1 = O2-C2
 1.43 with sigma of 0.002
3. Uiso/Uaniso restraints and constraints
O20 \\sim C23 \\sim C24 \\sim C25: within 2A with sigma of 0.005 and sigma for
terminal atoms of 0.01
4.a Riding coordinates:
 O20(H20)
4.b Ternary CH refined with riding coordinates:
 C23(H23)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N4(H4), N7(H7), N9(H9), N10(H10), C5(H5), C6(H6), C7(H7A),
 C16(H16), C17(H17), C18(H18)
4.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C),
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Eu1 Eu 0.40000(3) 0.79278(2) 0.65562(2) 0.04129(14) Uani 1 1 d . . . . .
P1 P 0.47370(15) 0.63454(10) 0.76942(9) 0.0459(4) Uani 1 1 d . . . . .
P2 P 0.50681(16) 0.96187(11) 0.76228(11) 0.0544(5) Uani 1 1 d . . . . .
P3 P 0.55412(19) 0.84424(12) 0.54399(10) 0.0608(5) Uani 1 1 d . . . . .
P4 P 0.21349(16) 0.65557(11) 0.54463(11) 0.0560(5) Uani 1 1 d . . . . .
O1 O 0.4483(4) 0.5479(2) 0.7467(3) 0.0529(12) Uani 1 1 d D . . . .
O2 O 0.4709(4) 0.6389(3) 0.8493(2) 0.0591(13) Uani 1 1 d D . . . .
O3 O 0.3910(4) 0.6883(3) 0.7288(2) 0.0512(12) Uani 1 1 d . . . . .
O4 O 0.5701(4) 0.7735(2) 0.7318(2) 0.0458(11) Uani 1 1 d . . . . .
O5 O 0.6712(4) 1.0711(3) 0.7434(3) 0.0658(14) Uani 1 1 d . . . . .
O6 O 0.5463(5) 0.9708(4) 0.8461(3) 0.0778(17) Uani 1 1 d D . . . .
O7 O 0.4596(5) 1.0402(3) 0.7386(3) 0.0819(18) Uani 1 1 d D . . . .
O8 O 0.4372(4) 0.8961(2) 0.7389(2) 0.0492(11) Uani 1 1 d . . . . .
O9 O 0.6522(6) 0.8983(4) 0.5570(4) 0.095(2) Uani 1 1 d D . . . .
O10 O 0.4985(6) 0.8592(4) 0.4647(3) 0.0890(19) Uani 1 1 d D . . . .
O11 O 0.4849(4) 0.8656(3) 0.5886(2) 0.0571(13) Uani 1 1 d . . . . .
O12 O 0.4797(4) 0.7001(2) 0.5951(3) 0.0496(12) Uani 1 1 d . . . . .
O13 O 0.1813(4) 0.4844(3) 0.5340(3) 0.0669(14) Uani 1 1 d . . . . .
O14 O 0.1653(6) 0.6506(3) 0.4630(3) 0.128(3) Uani 1 1 d D . . . .
O15 O 0.1243(6) 0.6374(4) 0.5726(6) 0.144(4) Uani 1 1 d D . . . .
O16 O 0.2658(4) 0.7300(3) 0.5672(3) 0.0542(12) Uani 1 1 d . . . . .
O17 O 0.2276(4) 0.8298(3) 0.6751(3) 0.0675(14) Uani 1 1 d . . . . .
O18 O 0.1136(6) 0.9028(5) 0.6044(4) 0.116(3) Uani 1 1 d . . . . .
O19 O 0.2689(5) 0.8923(3) 0.5931(3) 0.0701(15) Uani 1 1 d . . . . .
N1 N 0.6149(4) 0.9477(3) 0.7406(3) 0.0457(13) Uani 1 1 d . . . . .
H1 H 0.627278 0.901043 0.730103 0.055 Uiso 1 1 calc R . . . .
N2 N 0.7768(4) 0.9769(3) 0.7250(3) 0.0470(13) Uani 1 1 d . . . . .
H2 H 0.817342 1.012864 0.718269 0.056 Uiso 1 1 calc R . . . .
N3 N 0.7533(4) 0.8446(3) 0.7337(3) 0.0399(12) Uani 1 1 d . . . . .
N4 N 0.7252(4) 0.7122(3) 0.7475(3) 0.0446(13) Uani 1 1 d . . . . .
H4 H 0.756711 0.668537 0.757472 0.054 Uiso 1 1 calc R . . . .
N5 N 0.5898(4) 0.6441(3) 0.7648(3) 0.0466(13) Uani 1 1 d . . . . .
N6 N 0.6050(5) 0.7599(4) 0.5529(3) 0.0582(16) Uani 1 1 d . . . . .
N7 N 0.6186(5) 0.6326(4) 0.5820(3) 0.0544(15) Uani 1 1 d . . . . .
H7 H 0.681691 0.638134 0.580234 0.065 Uiso 1 1 calc R . . . .
N8 N 0.4899(5) 0.5432(3) 0.5817(3) 0.0490(14) Uani 1 1 d . . . . .
N9 N 0.3541(5) 0.4571(3) 0.5722(3) 0.0547(15) Uani 1 1 d . . . . .
H9 H 0.338256 0.409497 0.576405 0.066 Uiso 1 1 calc R . . . .
N10 N 0.2968(5) 0.5857(3) 0.5618(3) 0.0503(14) Uani 1 1 d . . . . .
H10 H 0.361838 0.597420 0.576630 0.060 Uiso 1 1 calc R . . . .
N11 N 0.2018(6) 0.8754(4) 0.6230(4) 0.074(2) Uani 1 1 d . . . . .
C1 C 0.3489(5) 0.5168(5) 0.7459(5) 0.073(2) Uani 1 1 d D . . . .
H1A H 0.295075 0.543073 0.710391 0.109 Uiso 1 1 calc GR . . . .
H1B H 0.337827 0.523745 0.792019 0.109 Uiso 1 1 calc GR . . . .
H1C H 0.346972 0.462609 0.734791 0.109 Uiso 1 1 calc GR . . . .
C2 C 0.5349(7) 0.5898(5) 0.9032(4) 0.087(3) Uani 1 1 d D . . . .
H2A H 0.507946 0.538003 0.896726 0.131 Uiso 1 1 calc GR . . . .
H2B H 0.534712 0.608287 0.949533 0.131 Uiso 1 1 calc GR . . . .
H2C H 0.604838 0.590103 0.899430 0.131 Uiso 1 1 calc GR . . . .
C3 C 0.6232(5) 0.7114(3) 0.7486(3) 0.0407(15) Uani 1 1 d . . . . .
C4 C 0.7859(5) 0.7713(4) 0.7333(3) 0.0453(15) Uani 1 1 d . . . . .
C5 C 0.8788(6) 0.7534(4) 0.7192(4) 0.060(2) Uani 1 1 d . . . . .
H5 H 0.899841 0.702320 0.717898 0.073 Uiso 1 1 calc R . . . .
C6 C 0.9403(7) 0.8143(5) 0.7069(5) 0.072(2) Uani 1 1 d . . . . .
H6 H 1.004282 0.804227 0.698794 0.086 Uiso 1 1 calc R . . . .
C7 C 0.9057(6) 0.8893(4) 0.7069(4) 0.062(2) Uani 1 1 d . . . . .
H7A H 0.944181 0.930579 0.697301 0.074 Uiso 1 1 calc R . . . .
C8 C 0.8132(5) 0.9010(4) 0.7214(3) 0.0438(15) Uani 1 1 d . . . . .
C9 C 0.6871(5) 1.0019(3) 0.7374(3) 0.0441(15) Uani 1 1 d . . . . .
C10 C 0.4758(6) 0.9694(6) 0.8891(4) 0.085(3) Uani 1 1 d D . . . .
H10A H 0.423775 1.008672 0.872934 0.127 Uiso 1 1 calc GR . . . .
H10B H 0.513533 0.978792 0.938085 0.127 Uiso 1 1 calc GR . . . .
H10C H 0.442780 0.919633 0.885032 0.127 Uiso 1 1 calc GR . . . .
C11 C 0.4155(9) 1.0562(7) 0.6642(3) 0.118(5) Uani 1 1 d D . . . .
H11A H 0.362255 1.018883 0.643843 0.178 Uiso 1 1 calc GR . . . .
H11B H 0.469048 1.053305 0.640348 0.178 Uiso 1 1 calc GR . . . .
H11C H 0.385775 1.107107 0.658482 0.178 Uiso 1 1 calc GR . . . .
C12 C 0.6482(13) 0.9789(4) 0.5404(7) 0.172(7) Uani 1 1 d D . . . .
H12A H 0.599620 0.987393 0.494323 0.258 Uiso 1 1 calc GR . . . .
H12B H 0.716107 0.996292 0.539956 0.258 Uiso 1 1 calc GR . . . .
H12C H 0.626191 1.007122 0.575952 0.258 Uiso 1 1 calc GR . . . .
C13 C 0.4021(7) 0.8214(6) 0.4310(6) 0.109(4) Uani 1 1 d D . . . .
H13A H 0.383942 0.829972 0.380299 0.164 Uiso 1 1 calc GR . . . .
H13B H 0.348291 0.841827 0.449468 0.164 Uiso 1 1 calc GR . . . .
H13C H 0.409214 0.766875 0.440466 0.164 Uiso 1 1 calc GR . . . .
C14 C 0.5631(6) 0.7004(4) 0.5770(3) 0.0472(16) Uani 1 1 d . . . . .
C15 C 0.5898(6) 0.5579(4) 0.5892(3) 0.0495(17) Uani 1 1 d . . . . .
C16 C 0.6642(6) 0.4990(5) 0.5991(4) 0.060(2) Uani 1 1 d . . . . .
H16 H 0.733736 0.509675 0.603141 0.072 Uiso 1 1 calc R . . . .
C17 C 0.6299(7) 0.4249(5) 0.6026(4) 0.065(2) Uani 1 1 d . . . . .
H17 H 0.677532 0.384506 0.609547 0.078 Uiso 1 1 calc R . . . .
C18 C 0.5285(7) 0.4087(4) 0.5963(4) 0.064(2) Uani 1 1 d . . . . .
H18 H 0.506020 0.358342 0.599581 0.076 Uiso 1 1 calc R . . . .
C19 C 0.4596(6) 0.4710(4) 0.5847(3) 0.0505(17) Uani 1 1 d . . . . .
C20 C 0.2703(6) 0.5069(4) 0.5541(4) 0.0537(18) Uani 1 1 d . . . . .
C21 C 0.1192(9) 0.7120(5) 0.4158(5) 0.100(4) Uani 1 1 d D . . . .
H21A H 0.127148 0.702007 0.369236 0.150 Uiso 1 1 calc GR . . . .
H21B H 0.152893 0.759852 0.433753 0.150 Uiso 1 1 calc GR . . . .
H21C H 0.046389 0.715443 0.412578 0.150 Uiso 1 1 calc GR . . . .
C22 C 0.0909(11) 0.6732(7) 0.6282(6) 0.126(5) Uani 1 1 d D . . . .
H22A H 0.046768 0.716464 0.609074 0.189 Uiso 1 1 calc GR . . . .
H22B H 0.150573 0.690831 0.665088 0.189 Uiso 1 1 calc GR . . . .
H22C H 0.052824 0.636495 0.647874 0.189 Uiso 1 1 calc GR . . . .
O20 O 0.6899(7) 0.7052(4) 0.4460(5) 0.128(3) Uani 1 1 d . U . . .
H20 H 0.662866 0.732424 0.470135 0.191 Uiso 1 1 d R . . . .
C23 C 0.7573(12) 0.7457(9) 0.4207(6) 0.153(4) Uani 1 1 d D U . . .
H23 H 0.715933 0.792590 0.404891 0.184 Uiso 1 1 calc R . . . .
C24 C 0.8424(12) 0.7781(11) 0.4768(8) 0.195(5) Uani 1 1 d D U . . .
H24A H 0.815752 0.816626 0.502455 0.293 Uiso 1 1 calc GR . . . .
H24B H 0.892020 0.801444 0.456030 0.293 Uiso 1 1 calc GR . . . .
H24C H 0.875685 0.737845 0.509074 0.293 Uiso 1 1 calc GR . . . .
C25 C 0.7658(13) 0.7179(8) 0.3525(7) 0.162(5) Uani 1 1 d D U . . .
H25A H 0.760838 0.662522 0.351184 0.243 Uiso 1 1 calc GR . . . .
H25B H 0.831714 0.733365 0.346579 0.243 Uiso 1 1 calc GR . . . .
H25C H 0.710467 0.739400 0.314627 0.243 Uiso 1 1 calc GR . . . .


_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
Eu1 P1 3.4852(17) . ?
Eu1 P3 3.514(2) . ?
Eu1 O3 2.328(4) . ?
Eu1 O4 2.362(4) . ?
Eu1 O8 2.372(4) . ?
Eu1 O11 2.332(5) . ?
Eu1 O12 2.411(4) . ?
Eu1 O16 2.370(5) . ?
Eu1 O17 2.525(5) . ?
Eu1 O19 2.513(5) . ?
Eu1 N11 2.920(7) . ?
P1 O1 1.573(5) . ?
P1 O2 1.571(5) . ?
P1 O3 1.489(5) . ?
P1 N5 1.590(6) . ?
P2 O6 1.578(6) . ?
P2 O7 1.511(6) . ?
P2 O8 1.458(5) . ?
P2 N1 1.637(6) . ?
P3 O9 1.573(7) . ?
P3 O10 1.537(6) . ?
P3 O11 1.486(5) . ?
P3 N6 1.599(7) . ?
P4 O14 1.541(6) . ?
P4 O15 1.480(7) . ?
P4 O16 1.472(5) . ?
P4 N10 1.614(6) . ?
O1 C1 1.432(2) . ?
O2 C2 1.431(2) . ?
O4 C3 1.278(7) . ?
O5 C9 1.228(7) . ?
O6 C10 1.429(2) . ?
O7 C11 1.429(2) . ?
O9 C12 1.427(2) . ?
O10 C13 1.430(2) . ?
O12 C14 1.264(8) . ?
O13 C20 1.208(9) . ?
O14 C21 1.426(2) . ?
O15 C22 1.427(2) . ?
O17 N11 1.255(9) . ?
O18 N11 1.227(9) . ?
O19 N11 1.237(9) . ?
N1 H1 0.8600 . ?
N1 C9 1.361(8) . ?
N2 H2 0.8600 . ?
N2 C8 1.409(8) . ?
N2 C9 1.360(8) . ?
N3 C4 1.342(8) . ?
N3 C8 1.327(8) . ?
N4 H4 0.8600 . ?
N4 C3 1.371(8) . ?
N4 C4 1.382(8) . ?
N5 C3 1.318(8) . ?
N6 C14 1.320(9) . ?
N7 H7 0.8600 . ?
N7 C14 1.377(9) . ?
N7 C15 1.367(9) . ?
N8 C15 1.328(9) . ?
N8 C19 1.319(9) . ?
N9 H9 0.8600 . ?
N9 C19 1.384(9) . ?
N9 C20 1.379(9) . ?
N10 H10 0.8600 . ?
N10 C20 1.405(9) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C4 C5 1.382(10) . ?
C5 H5 0.9300 . ?
C5 C6 1.399(11) . ?
C6 H6 0.9300 . ?
C6 C7 1.377(10) . ?
C7 H7A 0.9300 . ?
C7 C8 1.361(10) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 C16 1.399(10) . ?
C16 H16 0.9300 . ?
C16 C17 1.369(11) . ?
C17 H17 0.9300 . ?
C17 C18 1.356(12) . ?
C18 H18 0.9300 . ?
C18 C19 1.395(10) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
O20 H20 0.8199 . ?
O20 C23 1.342(13) . ?
C23 H23 0.9800 . ?
C23 C24 1.449(2) . ?
C23 C25 1.450(2) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
P1 Eu1 P3 118.95(5) . . ?
O3 Eu1 P1 18.94(12) . . ?
O3 Eu1 P3 135.97(12) . . ?
O3 Eu1 O4 73.36(16) . . ?
O3 Eu1 O8 101.65(17) . . ?
O3 Eu1 O11 151.91(17) . . ?
O3 Eu1 O12 83.79(16) . . ?
O3 Eu1 O16 86.00(17) . . ?
O3 Eu1 O17 83.99(19) . . ?
O3 Eu1 O19 132.8(2) . . ?
O3 Eu1 N11 108.1(2) . . ?
O4 Eu1 P1 56.02(11) . . ?
O4 Eu1 P3 78.15(12) . . ?
O4 Eu1 O8 72.42(15) . . ?
O4 Eu1 O12 74.50(16) . . ?
O4 Eu1 O16 142.07(15) . . ?
O4 Eu1 O17 134.41(17) . . ?
O4 Eu1 O19 144.80(17) . . ?
O4 Eu1 N11 149.27(17) . . ?
O8 Eu1 P1 100.89(11) . . ?
O8 Eu1 P3 100.84(12) . . ?
O8 Eu1 O12 143.16(16) . . ?
O8 Eu1 O17 74.27(17) . . ?
O8 Eu1 O19 78.35(17) . . ?
O8 Eu1 N11 77.35(17) . . ?
O11 Eu1 P1 133.37(13) . . ?
O11 Eu1 P3 18.09(12) . . ?
O11 Eu1 O4 83.81(17) . . ?
O11 Eu1 O8 86.37(16) . . ?
O11 Eu1 O12 74.34(16) . . ?
O11 Eu1 O16 103.21(17) . . ?
O11 Eu1 O17 124.05(19) . . ?
O11 Eu1 O19 75.1(2) . . ?
O11 Eu1 N11 99.9(2) . . ?
O12 Eu1 P1 72.87(11) . . ?
O12 Eu1 P3 56.33(11) . . ?
O12 Eu1 O17 142.41(17) . . ?
O12 Eu1 O19 124.25(18) . . ?
O12 Eu1 N11 136.04(18) . . ?
O16 Eu1 P1 97.04(12) . . ?
O16 Eu1 P3 97.00(13) . . ?
O16 Eu1 O8 144.29(16) . . ?
O16 Eu1 O12 71.86(16) . . ?
O16 Eu1 O17 71.92(17) . . ?
O16 Eu1 O19 71.36(17) . . ?
O16 Eu1 N11 67.18(18) . . ?
O17 Eu1 P1 102.02(15) . . ?
O17 Eu1 P3 138.74(15) . . ?
O17 Eu1 N11 25.4(2) . . ?
O19 Eu1 P1 151.56(16) . . ?
O19 Eu1 P3 88.71(16) . . ?
O19 Eu1 O17 50.0(2) . . ?
O19 Eu1 N11 24.9(2) . . ?
N11 Eu1 P1 126.7(2) . . ?
N11 Eu1 P3 113.5(2) . . ?
O1 P1 Eu1 124.70(19) . . ?
O1 P1 N5 102.6(3) . . ?
O2 P1 Eu1 120.80(19) . . ?
O2 P1 O1 105.2(3) . . ?
O2 P1 N5 110.6(3) . . ?
O3 P1 Eu1 30.50(19) . . ?
O3 P1 O1 112.1(3) . . ?
O3 P1 O2 105.9(3) . . ?
O3 P1 N5 119.7(3) . . ?
N5 P1 Eu1 89.23(19) . . ?
O6 P2 N1 102.9(3) . . ?
O7 P2 O6 102.5(3) . . ?
O7 P2 N1 112.3(3) . . ?
O8 P2 O6 113.3(3) . . ?
O8 P2 O7 115.4(3) . . ?
O8 P2 N1 109.6(3) . . ?
O9 P3 Eu1 131.4(3) . . ?
O9 P3 N6 102.4(4) . . ?
O10 P3 Eu1 117.7(3) . . ?
O10 P3 O9 101.8(4) . . ?
O10 P3 N6 109.4(4) . . ?
O11 P3 Eu1 29.16(18) . . ?
O11 P3 O9 112.9(4) . . ?
O11 P3 O10 110.1(4) . . ?
O11 P3 N6 118.7(3) . . ?
N6 P3 Eu1 90.5(2) . . ?
O14 P4 N10 103.5(4) . . ?
O15 P4 O14 103.0(6) . . ?
O15 P4 N10 110.3(4) . . ?
O16 P4 O14 112.4(3) . . ?
O16 P4 O15 116.1(4) . . ?
O16 P4 N10 110.6(3) . . ?
C1 O1 P1 119.1(5) . . ?
C2 O2 P1 121.5(5) . . ?
P1 O3 Eu1 130.6(3) . . ?
C3 O4 Eu1 130.2(4) . . ?
C10 O6 P2 121.6(6) . . ?
C11 O7 P2 120.0(7) . . ?
P2 O8 Eu1 142.4(3) . . ?
C12 O9 P3 124.6(9) . . ?
C13 O10 P3 120.1(6) . . ?
P3 O11 Eu1 132.8(3) . . ?
C14 O12 Eu1 133.1(4) . . ?
C21 O14 P4 127.1(6) . . ?
C22 O15 P4 130.4(7) . . ?
P4 O16 Eu1 144.7(3) . . ?
N11 O17 Eu1 95.2(5) . . ?
N11 O19 Eu1 96.3(5) . . ?
P2 N1 H1 116.5 . . ?
C9 N1 P2 126.9(4) . . ?
C9 N1 H1 116.5 . . ?
C8 N2 H2 115.1 . . ?
C9 N2 H2 115.1 . . ?
C9 N2 C8 129.8(6) . . ?
C8 N3 C4 118.6(6) . . ?
C3 N4 H4 114.5 . . ?
C3 N4 C4 131.0(5) . . ?
C4 N4 H4 114.5 . . ?
C3 N5 P1 120.6(5) . . ?
C14 N6 P3 122.6(6) . . ?
C14 N7 H7 114.7 . . ?
C15 N7 H7 114.7 . . ?
C15 N7 C14 130.6(7) . . ?
C19 N8 C15 119.2(6) . . ?
C19 N9 H9 114.7 . . ?
C20 N9 H9 114.7 . . ?
C20 N9 C19 130.7(6) . . ?
P4 N10 H10 117.8 . . ?
C20 N10 P4 124.4(5) . . ?
C20 N10 H10 117.8 . . ?
O17 N11 Eu1 59.5(4) . . ?
O18 N11 Eu1 172.4(6) . . ?
O18 N11 O17 120.2(10) . . ?
O18 N11 O19 122.4(9) . . ?
O19 N11 Eu1 58.8(4) . . ?
O19 N11 O17 117.4(7) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
O2 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O4 C3 N4 118.1(6) . . ?
O4 C3 N5 127.0(6) . . ?
N5 C3 N4 114.8(6) . . ?
N3 C4 N4 119.0(6) . . ?
N3 C4 C5 121.7(6) . . ?
N4 C4 C5 119.3(6) . . ?
C4 C5 H5 120.9 . . ?
C4 C5 C6 118.2(7) . . ?
C6 C5 H5 120.9 . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.6(8) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 H7A 121.1 . . ?
C8 C7 C6 117.7(7) . . ?
C8 C7 H7A 121.1 . . ?
N3 C8 N2 116.1(6) . . ?
N3 C8 C7 124.1(6) . . ?
C7 C8 N2 119.7(6) . . ?
O5 C9 N1 121.4(6) . . ?
O5 C9 N2 120.9(6) . . ?
N2 C9 N1 117.7(5) . . ?
O6 C10 H10A 109.5 . . ?
O6 C10 H10B 109.5 . . ?
O6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O7 C11 H11A 109.5 . . ?
O7 C11 H11B 109.5 . . ?
O7 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O9 C12 H12A 109.5 . . ?
O9 C12 H12B 109.5 . . ?
O9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O10 C13 H13A 109.5 . . ?
O10 C13 H13B 109.5 . . ?
O10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O12 C14 N6 127.0(7) . . ?
O12 C14 N7 118.6(6) . . ?
N6 C14 N7 114.4(7) . . ?
N7 C15 C16 119.4(7) . . ?
N8 C15 N7 118.3(6) . . ?
N8 C15 C16 122.1(7) . . ?
C15 C16 H16 121.6 . . ?
C17 C16 C15 116.9(8) . . ?
C17 C16 H16 121.6 . . ?
C16 C17 H17 119.0 . . ?
C18 C17 C16 122.0(7) . . ?
C18 C17 H17 119.0 . . ?
C17 C18 H18 121.5 . . ?
C17 C18 C19 116.9(8) . . ?
C19 C18 H18 121.5 . . ?
N8 C19 N9 117.9(6) . . ?
N8 C19 C18 122.8(8) . . ?
N9 C19 C18 119.2(7) . . ?
O13 C20 N9 122.5(7) . . ?
O13 C20 N10 122.9(7) . . ?
N9 C20 N10 114.6(7) . . ?
O14 C21 H21A 109.5 . . ?
O14 C21 H21B 109.5 . . ?
O14 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O15 C22 H22A 109.5 . . ?
O15 C22 H22B 109.5 . . ?
O15 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 O20 H20 111.3 . . ?
O20 C23 H23 99.8 . . ?
O20 C23 C24 113.0(11) . . ?
O20 C23 C25 113.6(10) . . ?
C24 C23 H23 99.8 . . ?
C24 C23 C25 124.8(14) . . ?
C25 C23 H23 99.8 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

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
_geom_hbond_publ_flag
N1 H1 N3 0.86 1.93 2.602(7) 133.7 . yes
N4 H4 O5 0.86 1.94 2.787(7) 166.4 2_646 yes
N9 H9 O20 0.86 2.04 2.869(8) 160.8 3_666 yes
N10 H10 N8 0.86 1.93 2.607(8) 134.5 . yes
O20 H20 N6 0.82 2.04 2.808(9) 156.9 . yes

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.148 0.051 0.521 30.5 0.0 ?
2 -0.148 0.949 0.479 30.5 0.0 ?
3 0.134 0.376 0.405 14.6 3.3 ?
4 0.352 0.551 0.979 30.5 0.0 ?
5 0.366 0.876 0.095 14.6 3.3 ?
6 0.648 0.449 0.021 30.5 0.0 ?
7 0.634 0.124 0.905 14.6 3.3 ?
8 0.866 0.624 0.595 14.6 3.3 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.757
_oxdiff_exptl_absorpt_empirical_full_min 0.711
####################################################################### 
# 
# 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_kiev301_lt
_database_code_depnum_ccdc_archive 'CCDC 1984338'
loop_
_audit_author_name
_audit_author_address
'Viktoriya Dyakonenko'
;SSI Institute for Single Crystals National Academy of Sciences of Ukraine
Ukraine
;
_audit_update_record             
;
2020-02-16 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;
_audit_creation_date             2020-02-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H36 N11 O19 P4 Tb, C3 H8 O'
_chemical_formula_sum            'C25 H44 N11 O20 P4 Tb'
_chemical_formula_weight         1101.51
_chemical_melting_point          ?
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'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.134(2)
_cell_length_b                   17.152(2)
_cell_length_c                   19.453(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.506(19)
_cell_angle_gamma                90
_cell_volume                     4179.6(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    934
_cell_measurement_temperature    110
_cell_measurement_theta_max      18.6650
_cell_measurement_theta_min      3.2450
_shelx_estimated_absorpt_T_max   0.698
_shelx_estimated_absorpt_T_min   0.445
_exptl_absorpt_coefficient_mu    1.935
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2224
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1810
_diffrn_reflns_av_unetI/netI     0.1656
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            33047
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.901
_diffrn_ambient_temperature      110
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1827
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    9.00   94.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7645   57.0000  150.0000 85

#__ type_ start__ end____ width___ exp.time_
  2 omega   -9.00   69.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7645  -99.0000 -120.0000 78

#__ type_ start__ end____ width___ exp.time_
  3 omega   26.00   69.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7645  -99.0000   30.0000 43

#__ type_ start__ end____ width___ exp.time_
  4 omega  -38.00   11.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7645  -57.0000  -90.0000 49

#__ type_ start__ end____ width___ exp.time_
  5 omega   12.00   38.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7645  -57.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega  -14.00   44.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7645  -57.0000  -60.0000 58

#__ type_ start__ end____ width___ exp.time_
  7 omega   36.00   61.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7645 -178.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
  8 omega   27.00   57.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7645  -77.0000  120.0000 30

#__ type_ start__ end____ width___ exp.time_
  9 omega   -4.00   99.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7645   19.0000   90.0000 103
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0192364000
_diffrn_orient_matrix_UB_12      0.0071071000
_diffrn_orient_matrix_UB_13      -0.0375927000
_diffrn_orient_matrix_UB_21      -0.0442989000
_diffrn_orient_matrix_UB_22      -0.0246795000
_diffrn_orient_matrix_UB_23      -0.0024423000
_diffrn_orient_matrix_UB_31      -0.0294480000
_diffrn_orient_matrix_UB_32      0.0324787000
_diffrn_orient_matrix_UB_33      0.0063158000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4081
_reflns_number_total             7352
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.858
_refine_diff_density_min         -1.602
_refine_diff_density_rms         0.183
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     560
_refine_ls_number_reflns         7352
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1448
_refine_ls_R_factor_gt           0.0790
_refine_ls_restrained_S_all      0.983
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0753P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1684
_refine_ls_wR_factor_ref         0.2067
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: -1(10)
 2(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Restrained distances
 O10-C13B
 1.45 with sigma of 0.002
 O10-C13A
 1.45 with sigma of 0.002
4. Uiso/Uaniso restraints and constraints
Uanis(C13B) = Uanis(C13A)
Uanis(C25) = Uanis(C24)
5. Others
 Fixed Sof: C13A(0.5) H13A(0.5) H13B(0.5) H13C(0.5) C13B(0.5) H13D(0.5)
 H13E(0.5) H13F(0.5)
6.a Ternary CH refined with riding coordinates:
 C23(H23)
6.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N4(H4), N5(H5), N7(H7), N9(H9), N10(H10), C5(H5A), C6(H6), C7(H7A),
 C16(H16), C17(H17), C18(H18)
6.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C),
 C12(H12A,H12B,H12C), C13A(H13A,H13B,H13C), C13B(H13D,H13E,H13F), C21(H21A,H21B,
 H21C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
6.d Idealised tetrahedral OH refined as rotating group:
 O20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Tb1 Tb 0.39196(5) 0.20773(3) 0.65651(3) 0.0336(2) Uani 1 1 d . . . . .
P1 P 0.4673(3) 0.36753(16) 0.76906(17) 0.0319(7) Uani 1 1 d . . . . .
P2 P 0.5030(3) 0.04011(16) 0.76432(17) 0.0334(7) Uani 1 1 d . . . . .
P3 P 0.5452(3) 0.1472(2) 0.5476(2) 0.0574(11) Uani 1 1 d . . . . .
P4 P 0.2078(3) 0.34581(17) 0.53981(19) 0.0379(8) Uani 1 1 d . . . . .
O1 O 0.4623(7) 0.3624(4) 0.8502(4) 0.039(2) Uani 1 1 d . . . . .
O2 O 0.4412(6) 0.4556(4) 0.7467(4) 0.0324(18) Uani 1 1 d . . . . .
O3 O 0.3816(7) 0.3137(4) 0.7271(4) 0.039(2) Uani 1 1 d . . . . .
O4 O 0.5667(6) 0.2273(4) 0.7349(4) 0.0311(18) Uani 1 1 d . . . . .
O5 O 0.6659(6) -0.0723(4) 0.7393(4) 0.0352(19) Uani 1 1 d . . . . .
O6 O 0.4530(7) -0.0414(4) 0.7384(4) 0.039(2) Uani 1 1 d . . . . .
O7 O 0.5452(7) 0.0290(4) 0.8464(4) 0.040(2) Uani 1 1 d . . . . .
O8 O 0.4282(7) 0.1052(4) 0.7393(4) 0.035(2) Uani 1 1 d . . . . .
O9 O 0.4889(8) 0.1292(6) 0.4660(5) 0.069(3) Uani 1 1 d . . . . .
O10 O 0.6370(8) 0.0854(6) 0.5681(6) 0.084(4) Uani 1 1 d D . . . .
O11 O 0.4732(7) 0.1312(4) 0.5913(4) 0.040(2) Uani 1 1 d . . . . .
O12 O 0.4757(7) 0.2964(4) 0.5961(4) 0.0349(19) Uani 1 1 d . . . . .
O13 O 0.1822(7) 0.5212(4) 0.5319(5) 0.045(2) Uani 1 1 d . . . . .
O14 O 0.2586(7) 0.2710(4) 0.5672(4) 0.042(2) Uani 1 1 d . . . . .
O15 O 0.1060(8) 0.3639(5) 0.5605(5) 0.056(3) Uani 1 1 d . . . . .
O16 O 0.1681(8) 0.3495(5) 0.4545(4) 0.052(2) Uani 1 1 d . . . . .
O17 O 0.2178(7) 0.1754(4) 0.6775(4) 0.040(2) Uani 1 1 d . . . . .
O18 O 0.0975(8) 0.0999(5) 0.6073(6) 0.064(3) Uani 1 1 d . . . . .
O19 O 0.2593(7) 0.1077(4) 0.5959(5) 0.042(2) Uani 1 1 d . . . . .
N1 N 0.5867(7) 0.3573(4) 0.7663(5) 0.024(2) Uani 1 1 d . . . . .
N2 N 0.7244(7) 0.2883(5) 0.7492(5) 0.033(2) Uani 1 1 d . . . . .
H2 H 0.757567 0.333134 0.761301 0.039 Uiso 1 1 calc R . . . .
N3 N 0.7522(8) 0.1564(5) 0.7324(5) 0.027(2) Uani 1 1 d . . . . .
N4 N 0.7753(8) 0.0215(5) 0.7238(5) 0.034(2) Uani 1 1 d . . . . .
H4 H 0.817921 -0.015608 0.717679 0.041 Uiso 1 1 calc R . . . .
N5 N 0.6115(8) 0.0529(4) 0.7404(5) 0.032(2) Uani 1 1 d . . . . .
H5 H 0.626083 0.101054 0.730964 0.038 Uiso 1 1 calc R . . . .
N6 N 0.6005(9) 0.2323(6) 0.5543(6) 0.046(3) Uani 1 1 d . . . . .
N7 N 0.6237(8) 0.3600(7) 0.5823(6) 0.050(3) Uani 1 1 d . . . . .
H7 H 0.689196 0.351978 0.580893 0.060 Uiso 1 1 calc R . . . .
N8 N 0.4918(8) 0.4543(5) 0.5839(5) 0.035(2) Uani 1 1 d . . . . .
N9 N 0.3580(9) 0.5444(5) 0.5740(5) 0.041(3) Uani 1 1 d . . . . .
H9 H 0.342436 0.593129 0.580855 0.049 Uiso 1 1 calc R . . . .
N10 N 0.2947(7) 0.4163(5) 0.5632(5) 0.033(2) Uani 1 1 d . . . . .
H10 H 0.361785 0.403318 0.583929 0.039 Uiso 1 1 calc R . . . .
N11 N 0.1892(9) 0.1276(6) 0.6269(7) 0.049(3) Uani 1 1 d . . . . .
C1 C 0.5308(11) 0.4112(6) 0.9041(7) 0.046(3) Uani 1 1 d . . . . .
H1A H 0.508190 0.465611 0.894805 0.069 Uiso 1 1 calc GR . . . .
H1B H 0.604436 0.405695 0.902692 0.069 Uiso 1 1 calc GR . . . .
H1C H 0.526842 0.395655 0.951686 0.069 Uiso 1 1 calc GR . . . .
C2 C 0.3365(9) 0.4868(7) 0.7453(7) 0.040(3) Uani 1 1 d . . . . .
H2A H 0.280885 0.463007 0.705487 0.061 Uiso 1 1 calc GR . . . .
H2B H 0.335893 0.543466 0.738575 0.061 Uiso 1 1 calc GR . . . .
H2C H 0.322843 0.474828 0.791010 0.061 Uiso 1 1 calc GR . . . .
C3 C 0.6204(9) 0.2889(6) 0.7492(5) 0.024(2) Uani 1 1 d . . . . .
C4 C 0.7880(10) 0.2296(6) 0.7336(6) 0.034(3) Uani 1 1 d . . . . .
C5 C 0.8822(9) 0.2487(6) 0.7204(6) 0.033(3) Uani 1 1 d . . . . .
H5A H 0.903829 0.301410 0.719693 0.040 Uiso 1 1 calc R . . . .
C6 C 0.9441(11) 0.1880(7) 0.7084(7) 0.043(3) Uani 1 1 d . . . . .
H6 H 1.010397 0.198713 0.700054 0.052 Uiso 1 1 calc R . . . .
C7 C 0.9093(10) 0.1116(6) 0.7084(6) 0.037(3) Uani 1 1 d . . . . .
H7A H 0.949769 0.069079 0.699199 0.044 Uiso 1 1 calc R . . . .
C8 C 0.8141(9) 0.1001(6) 0.7224(6) 0.029(3) Uani 1 1 d . . . . .
C9 C 0.6817(10) -0.0033(6) 0.7334(7) 0.036(3) Uani 1 1 d . . . . .
C10 C 0.4086(12) -0.0558(8) 0.6612(7) 0.057(4) Uani 1 1 d . . . . .
H10A H 0.439093 -0.018519 0.634631 0.085 Uiso 1 1 calc GR . . . .
H10B H 0.330900 -0.049403 0.646903 0.085 Uiso 1 1 calc GR . . . .
H10C H 0.426066 -0.108977 0.650312 0.085 Uiso 1 1 calc GR . . . .
C11 C 0.4719(11) 0.0338(7) 0.8907(7) 0.046(3) Uani 1 1 d . . . . .
H11A H 0.421204 -0.009639 0.878673 0.069 Uiso 1 1 calc GR . . . .
H11B H 0.432826 0.083275 0.881068 0.069 Uiso 1 1 calc GR . . . .
H11C H 0.513026 0.031059 0.941866 0.069 Uiso 1 1 calc GR . . . .
C12 C 0.3950(14) 0.1699(9) 0.4314(9) 0.080(5) Uani 1 1 d . . . . .
H12A H 0.380004 0.165426 0.379041 0.119 Uiso 1 1 calc GR . . . .
H12B H 0.403850 0.224972 0.445328 0.119 Uiso 1 1 calc GR . . . .
H12C H 0.335520 0.147772 0.445537 0.119 Uiso 1 1 calc GR . . . .
C13A C 0.633(3) 0.0102(9) 0.5335(15) 0.088(9) Uani 0.5 1 d D . P A 1
H13A H 0.595945 -0.027236 0.555593 0.133 Uiso 0.5 1 calc GR . P A 1
H13B H 0.705858 -0.008134 0.539511 0.133 Uiso 0.5 1 calc GR . P A 1
H13C H 0.594628 0.015150 0.482043 0.133 Uiso 0.5 1 calc GR . P A 1
C13B C 0.716(2) 0.0638(18) 0.5330(16) 0.088(9) Uani 0.5 1 d D . P A 2
H13D H 0.679694 0.041418 0.485537 0.133 Uiso 0.5 1 calc GR . P A 2
H13E H 0.764792 0.025204 0.562493 0.133 Uiso 0.5 1 calc GR . P A 2
H13F H 0.755994 0.110145 0.527144 0.133 Uiso 0.5 1 calc GR . P A 2
C14 C 0.5584(10) 0.2927(7) 0.5764(6) 0.040(3) Uani 1 1 d . . . . .
C15 C 0.5957(10) 0.4373(7) 0.5899(7) 0.041(3) Uani 1 1 d . . . . .
C16 C 0.6726(12) 0.4948(9) 0.5982(7) 0.054(4) Uani 1 1 d . . . . .
H16 H 0.743406 0.481936 0.599361 0.065 Uiso 1 1 calc R . . . .
C17 C 0.6442(13) 0.5703(9) 0.6046(7) 0.060(4) Uani 1 1 d . . . . .
H17 H 0.696853 0.610063 0.613551 0.072 Uiso 1 1 calc R . . . .
C18 C 0.5399(13) 0.5894(7) 0.5983(7) 0.052(4) Uani 1 1 d . . . . .
H18 H 0.519176 0.641780 0.602469 0.062 Uiso 1 1 calc R . . . .
C19 C 0.4663(11) 0.5288(7) 0.5857(7) 0.040(3) Uani 1 1 d . . . . .
C20 C 0.2718(10) 0.4940(6) 0.5533(7) 0.038(3) Uani 1 1 d . . . . .
C21 C 0.0888(13) 0.3346(7) 0.6240(8) 0.058(4) Uani 1 1 d . . . . .
H21A H 0.091146 0.277547 0.623512 0.086 Uiso 1 1 calc GR . . . .
H21B H 0.018718 0.351791 0.626330 0.086 Uiso 1 1 calc GR . . . .
H21C H 0.144501 0.354284 0.666120 0.086 Uiso 1 1 calc GR . . . .
C22 C 0.1070(11) 0.2882(6) 0.4138(6) 0.045(3) Uani 1 1 d . . . . .
H22A H 0.082075 0.303211 0.362807 0.068 Uiso 1 1 calc GR . . . .
H22B H 0.045477 0.277653 0.430902 0.068 Uiso 1 1 calc GR . . . .
H22C H 0.151237 0.241222 0.419243 0.068 Uiso 1 1 calc GR . . . .
O20 O 0.6741(11) 0.2890(6) 0.4414(7) 0.089(4) Uani 1 1 d . . . . .
H20 H 0.651926 0.262985 0.470543 0.133 Uiso 1 1 calc GR . . . .
C23 C 0.7523(13) 0.2469(9) 0.4228(8) 0.063(4) Uani 1 1 d . . . . .
H23 H 0.733399 0.190280 0.417148 0.075 Uiso 1 1 calc R . . . .
C24 C 0.7596(17) 0.2804(11) 0.3532(9) 0.100(5) Uani 1 1 d . . . . .
H24A H 0.687550 0.289978 0.320807 0.151 Uiso 1 1 calc GR . . . .
H24B H 0.796582 0.243438 0.330516 0.151 Uiso 1 1 calc GR . . . .
H24C H 0.799345 0.329534 0.362727 0.151 Uiso 1 1 calc GR . . . .
C25 C 0.8463(17) 0.2594(12) 0.4845(10) 0.100(5) Uani 1 1 d . . . . .
H25A H 0.826241 0.288894 0.521533 0.151 Uiso 1 1 calc GR . . . .
H25B H 0.899810 0.288745 0.469217 0.151 Uiso 1 1 calc GR . . . .
H25C H 0.876240 0.208899 0.504189 0.151 Uiso 1 1 calc GR . . . .


_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
Tb1 O3 2.307(7) . ?
Tb1 O4 2.366(8) . ?
Tb1 O8 2.335(7) . ?
Tb1 O11 2.298(6) . ?
Tb1 O12 2.384(7) . ?
Tb1 O14 2.331(8) . ?
Tb1 O17 2.504(8) . ?
Tb1 O19 2.476(8) . ?
Tb1 N11 2.897(10) . ?
P1 O1 1.602(8) . ?
P1 O2 1.582(7) . ?
P1 O3 1.494(9) . ?
P1 N1 1.595(9) . ?
P2 O6 1.562(8) . ?
P2 O7 1.537(8) . ?
P2 O8 1.470(8) . ?
P2 N5 1.642(9) . ?
P3 O9 1.567(10) . ?
P3 O10 1.565(10) . ?
P3 O11 1.475(8) . ?
P3 N6 1.618(11) . ?
P4 O14 1.470(8) . ?
P4 O15 1.540(9) . ?
P4 O16 1.584(8) . ?
P4 N10 1.632(9) . ?
O1 C1 1.428(14) . ?
O2 C2 1.469(13) . ?
O4 C3 1.254(12) . ?
O5 C9 1.213(11) . ?
O6 C10 1.459(14) . ?
O7 C11 1.475(12) . ?
O9 C12 1.400(17) . ?
O10 C13A 1.449(2) . ?
O10 C13B 1.449(2) . ?
O12 C14 1.256(13) . ?
O13 C20 1.217(14) . ?
O15 C21 1.412(14) . ?
O16 C22 1.412(13) . ?
O17 N11 1.250(13) . ?
O18 N11 1.243(13) . ?
O19 N11 1.289(13) . ?
N1 C3 1.332(12) . ?
N2 H2 0.8800 . ?
N2 C3 1.366(13) . ?
N2 C4 1.398(13) . ?
N3 C4 1.339(13) . ?
N3 C8 1.315(12) . ?
N4 H4 0.8800 . ?
N4 C8 1.444(12) . ?
N4 C9 1.366(14) . ?
N5 H5 0.8800 . ?
N5 C9 1.367(13) . ?
N6 C14 1.307(14) . ?
N7 H7 0.8800 . ?
N7 C14 1.422(16) . ?
N7 C15 1.395(15) . ?
N8 C15 1.365(15) . ?
N8 C19 1.324(14) . ?
N9 H9 0.8800 . ?
N9 C19 1.397(15) . ?
N9 C20 1.386(15) . ?
N10 H10 0.8800 . ?
N10 C20 1.366(13) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C4 C5 1.375(15) . ?
C5 H5A 0.9500 . ?
C5 C6 1.383(15) . ?
C6 H6 0.9500 . ?
C6 C7 1.389(14) . ?
C7 H7A 0.9500 . ?
C7 C8 1.371(15) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
C15 C16 1.386(17) . ?
C16 H16 0.9500 . ?
C16 C17 1.363(19) . ?
C17 H17 0.9500 . ?
C17 C18 1.38(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.390(17) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
O20 H20 0.8400 . ?
O20 C23 1.390(15) . ?
C23 H23 1.0000 . ?
C23 C24 1.500(19) . ?
C23 C25 1.46(2) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Tb1 O4 74.0(3) . . ?
O3 Tb1 O8 102.7(3) . . ?
O3 Tb1 O12 84.8(3) . . ?
O3 Tb1 O14 84.9(3) . . ?
O3 Tb1 O17 81.8(3) . . ?
O3 Tb1 O19 132.1(3) . . ?
O3 Tb1 N11 106.1(3) . . ?
O4 Tb1 O12 74.0(3) . . ?
O4 Tb1 O17 133.1(3) . . ?
O4 Tb1 O19 144.3(2) . . ?
O4 Tb1 N11 148.3(3) . . ?
O8 Tb1 O4 72.9(3) . . ?
O8 Tb1 O12 142.4(3) . . ?
O8 Tb1 O17 74.2(3) . . ?
O8 Tb1 O19 77.0(3) . . ?
O8 Tb1 N11 76.4(3) . . ?
O11 Tb1 O3 154.0(3) . . ?
O11 Tb1 O4 85.1(3) . . ?
O11 Tb1 O8 85.3(3) . . ?
O11 Tb1 O12 74.5(3) . . ?
O11 Tb1 O14 103.0(3) . . ?
O11 Tb1 O17 124.2(3) . . ?
O11 Tb1 O19 73.7(3) . . ?
O11 Tb1 N11 99.8(3) . . ?
O12 Tb1 O17 143.3(3) . . ?
O12 Tb1 O19 124.8(3) . . ?
O12 Tb1 N11 137.5(3) . . ?
O14 Tb1 O4 141.2(3) . . ?
O14 Tb1 O8 144.7(3) . . ?
O14 Tb1 O12 72.0(3) . . ?
O14 Tb1 O17 72.9(3) . . ?
O14 Tb1 O19 72.8(3) . . ?
O14 Tb1 N11 68.5(3) . . ?
O17 Tb1 N11 25.5(3) . . ?
O19 Tb1 O17 51.5(3) . . ?
O19 Tb1 N11 26.3(3) . . ?
O2 P1 O1 104.7(4) . . ?
O2 P1 N1 103.3(4) . . ?
O3 P1 O1 104.9(4) . . ?
O3 P1 O2 112.0(5) . . ?
O3 P1 N1 120.0(4) . . ?
N1 P1 O1 111.1(5) . . ?
O6 P2 N5 110.1(4) . . ?
O7 P2 O6 102.1(4) . . ?
O7 P2 N5 103.8(5) . . ?
O8 P2 O6 113.5(5) . . ?
O8 P2 O7 115.8(4) . . ?
O8 P2 N5 110.8(4) . . ?
O9 P3 N6 108.8(6) . . ?
O10 P3 O9 102.5(6) . . ?
O10 P3 N6 107.3(6) . . ?
O11 P3 O9 111.0(6) . . ?
O11 P3 O10 107.8(6) . . ?
O11 P3 N6 118.1(5) . . ?
O14 P4 O15 114.6(5) . . ?
O14 P4 O16 112.7(5) . . ?
O14 P4 N10 110.0(5) . . ?
O15 P4 O16 103.2(6) . . ?
O15 P4 N10 111.6(5) . . ?
O16 P4 N10 104.2(5) . . ?
C1 O1 P1 119.1(7) . . ?
C2 O2 P1 118.5(7) . . ?
P1 O3 Tb1 130.0(5) . . ?
C3 O4 Tb1 129.3(7) . . ?
C10 O6 P2 118.8(7) . . ?
C11 O7 P2 120.4(8) . . ?
P2 O8 Tb1 141.0(4) . . ?
C12 O9 P3 117.9(9) . . ?
C13A O10 P3 124.6(15) . . ?
C13B O10 P3 131.1(14) . . ?
P3 O11 Tb1 134.1(4) . . ?
C14 O12 Tb1 133.4(7) . . ?
P4 O14 Tb1 146.5(5) . . ?
C21 O15 P4 122.5(9) . . ?
C22 O16 P4 120.8(7) . . ?
N11 O17 Tb1 95.1(7) . . ?
N11 O19 Tb1 95.4(6) . . ?
C3 N1 P1 120.7(7) . . ?
C3 N2 H2 114.1 . . ?
C3 N2 C4 131.9(9) . . ?
C4 N2 H2 114.1 . . ?
C8 N3 C4 117.5(10) . . ?
C8 N4 H4 115.4 . . ?
C9 N4 H4 115.4 . . ?
C9 N4 C8 129.2(9) . . ?
P2 N5 H5 116.5 . . ?
C9 N5 P2 127.1(7) . . ?
C9 N5 H5 116.5 . . ?
C14 N6 P3 121.2(10) . . ?
C14 N7 H7 116.3 . . ?
C15 N7 H7 116.3 . . ?
C15 N7 C14 127.4(11) . . ?
C19 N8 C15 117.3(10) . . ?
C19 N9 H9 115.5 . . ?
C20 N9 H9 115.5 . . ?
C20 N9 C19 129.1(10) . . ?
P4 N10 H10 117.4 . . ?
C20 N10 P4 125.2(9) . . ?
C20 N10 H10 117.4 . . ?
O17 N11 Tb1 59.4(6) . . ?
O17 N11 O19 117.0(10) . . ?
O18 N11 Tb1 172.0(9) . . ?
O18 N11 O17 121.8(12) . . ?
O18 N11 O19 121.2(12) . . ?
O19 N11 Tb1 58.3(5) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
O2 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O4 C3 N1 126.2(10) . . ?
O4 C3 N2 119.3(9) . . ?
N1 C3 N2 114.5(9) . . ?
N3 C4 N2 116.7(10) . . ?
N3 C4 C5 123.4(10) . . ?
C5 C4 N2 119.9(9) . . ?
C4 C5 H5A 121.3 . . ?
C4 C5 C6 117.5(10) . . ?
C6 C5 H5A 121.3 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.0(12) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7A 121.4 . . ?
C8 C7 C6 117.1(11) . . ?
C8 C7 H7A 121.4 . . ?
N3 C8 N4 116.4(10) . . ?
N3 C8 C7 124.4(10) . . ?
C7 C8 N4 119.2(9) . . ?
O5 C9 N4 120.2(10) . . ?
O5 C9 N5 122.6(11) . . ?
N4 C9 N5 117.1(9) . . ?
O6 C10 H10A 109.5 . . ?
O6 C10 H10B 109.5 . . ?
O6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O7 C11 H11A 109.5 . . ?
O7 C11 H11B 109.5 . . ?
O7 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O9 C12 H12A 109.5 . . ?
O9 C12 H12B 109.5 . . ?
O9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O10 C13A H13A 109.5 . . ?
O10 C13A H13B 109.5 . . ?
O10 C13A H13C 109.5 . . ?
H13A C13A H13B 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
O10 C13B H13D 109.5 . . ?
O10 C13B H13E 109.5 . . ?
O10 C13B H13F 109.5 . . ?
H13D C13B H13E 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
O12 C14 N6 129.1(12) . . ?
O12 C14 N7 119.4(11) . . ?
N6 C14 N7 111.4(11) . . ?
N8 C15 N7 118.8(10) . . ?
N8 C15 C16 122.1(12) . . ?
C16 C15 N7 118.9(12) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 C15 118.5(14) . . ?
C17 C16 H16 120.8 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.6(13) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 121.4 . . ?
C17 C18 C19 117.3(13) . . ?
C19 C18 H18 121.4 . . ?
N8 C19 N9 115.8(10) . . ?
N8 C19 C18 123.9(13) . . ?
C18 C19 N9 120.3(11) . . ?
O13 C20 N9 118.8(10) . . ?
O13 C20 N10 124.9(11) . . ?
N10 C20 N9 116.2(11) . . ?
O15 C21 H21A 109.5 . . ?
O15 C21 H21B 109.5 . . ?
O15 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O16 C22 H22A 109.5 . . ?
O16 C22 H22B 109.5 . . ?
O16 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 O20 H20 109.5 . . ?
O20 C23 H23 110.8 . . ?
O20 C23 C24 106.8(13) . . ?
O20 C23 C25 102.6(13) . . ?
C24 C23 H23 110.8 . . ?
C25 C23 H23 110.8 . . ?
C25 C23 C24 114.8(16) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

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
_geom_hbond_publ_flag
N2 H2 O5 0.88 1.91 2.765(11) 163.6 2_656 yes
N5 H5 N3 0.88 1.90 2.601(12) 135.1 . yes
N9 H9 O20 0.88 2.06 2.891(13) 155.9 3_666 yes
N10 H10 N8 0.88 1.92 2.581(13) 130.7 . yes
C13A H13A O9 0.98 2.05 2.88(3) 141.4 3_656 yes
O20 H20 N6 0.84 2.01 2.826(13) 162.7 . yes

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 -1(10)
2 2(10)

####################################################################### 
# 
# 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_k300a
_database_code_depnum_ccdc_archive 'CCDC 1984337'
loop_
_audit_author_name
_audit_author_address
'Viktoriya Dyakonenko'
;SSI Institute for Single Crystals National Academy of Sciences of Ukraine
Ukraine
;
_audit_update_record             
;
2020-02-16 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;
_audit_creation_date             2020-02-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H18 N5 Na O8 P2, C3 H8 O'
_chemical_formula_sum            'C14 H26 N5 Na O9 P2'
_chemical_formula_weight         493.33
_chemical_melting_point          ?
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'
Na Na 0.0362 0.0249 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   13.740(2)
_cell_length_b                   17.912(3)
_cell_length_c                   9.9299(15)
_cell_angle_alpha                90
_cell_angle_beta                 108.507(16)
_cell_angle_gamma                90
_cell_volume                     2317.5(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    837
_cell_measurement_temperature    294
_cell_measurement_theta_max      18.8020
_cell_measurement_theta_min      3.3830
_shelx_estimated_absorpt_T_max   0.950
_shelx_estimated_absorpt_T_min   0.881
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1295
_diffrn_reflns_av_unetI/netI     0.1453
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20367
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         3.127
_diffrn_ambient_temperature      294
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1827
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -23.00    3.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.3583  -77.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega    0.00   77.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7645   77.0000  120.0000 77

#__ type_ start__ end____ width___ exp.time_
  3 omega  -42.00   14.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7645  -57.0000   60.0000 56

#__ type_ start__ end____ width___ exp.time_
  4 omega   23.00   69.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7645  -99.0000    0.0000 46

#__ type_ start__ end____ width___ exp.time_
  5 omega   19.00   96.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7645   57.0000 -150.0000 77

#__ type_ start__ end____ width___ exp.time_
  6 omega  -12.00   70.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7645   19.0000   60.0000 82

#__ type_ start__ end____ width___ exp.time_
  7 omega    6.00   89.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7645   57.0000  -60.0000 83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0366633000
_diffrn_orient_matrix_UB_12      -0.0292764000
_diffrn_orient_matrix_UB_13      0.0156133000
_diffrn_orient_matrix_UB_21      0.0186185000
_diffrn_orient_matrix_UB_22      0.0127180000
_diffrn_orient_matrix_UB_23      -0.0548944000
_diffrn_orient_matrix_UB_31      0.0356096000
_diffrn_orient_matrix_UB_32      0.0234820000
_diffrn_orient_matrix_UB_33      0.0491756000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2506
_reflns_number_total             5320
_reflns_odcompleteness_completeness 89.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.35
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         5320
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.2012
_refine_ls_R_factor_gt           0.0964
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0667P)²+1.1471P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1778
_refine_ls_wR_factor_ref         0.2182
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
O9 \\sim C12 \\sim C13 \\sim C14: within 1.8A with sigma of 0.005 and sigma for
terminal atoms of 0.01
3.a Ternary CH refined with riding coordinates:
 C12(H12)
3.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N4(H4), N5(H5), C5(H5A), C6(H6), C7(H7)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C),
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
3.d Idealised tetrahedral OH refined as rotating group:
 O9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.72512(11) 0.50006(9) 0.60896(16) 0.0508(4) Uani 1 1 d . . . . .
P2 P 0.43469(11) 0.65310(9) 0.05434(15) 0.0486(4) Uani 1 1 d . . . . .
Na1 Na 0.51295(14) 0.57428(11) 0.3924(2) 0.0414(5) Uani 1 1 d . . . . .
O1 O 0.7436(4) 0.5686(3) 0.7148(5) 0.0979(17) Uani 1 1 d . . . . .
O2 O 0.7853(3) 0.4401(3) 0.7160(5) 0.0972(18) Uani 1 1 d . . . . .
O3 O 0.6165(3) 0.4829(2) 0.5455(4) 0.0553(11) Uani 1 1 d . . . . .
O4 O 0.6776(2) 0.60153(18) 0.3683(3) 0.0381(8) Uani 1 1 d . . . . .
O5 O 0.5004(3) 0.8015(2) -0.0405(4) 0.0579(11) Uani 1 1 d . . . . .
O6 O 0.3509(3) 0.7133(3) 0.0379(5) 0.0727(13) Uani 1 1 d . . . . .
O7 O 0.4034(5) 0.6279(3) -0.1028(5) 0.112(2) Uani 1 1 d . . . . .
O8 O 0.4418(3) 0.5935(2) 0.1559(4) 0.0506(10) Uani 1 1 d . . . . .
N1 N 0.7931(3) 0.5176(2) 0.5088(4) 0.0455(11) Uani 1 1 d . . . . .
N2 N 0.8267(3) 0.5737(2) 0.3257(4) 0.0431(11) Uani 1 1 d . . . . .
H2 H 0.874043 0.540365 0.341695 0.052 Uiso 1 1 calc R . . . .
N3 N 0.7478(3) 0.6708(2) 0.1735(4) 0.0400(10) Uani 1 1 d . . . . .
N4 N 0.6650(3) 0.7669(2) 0.0246(5) 0.0492(12) Uani 1 1 d . . . . .
H4 H 0.675434 0.807511 -0.015015 0.059 Uiso 1 1 calc R . . . .
N5 N 0.5463(3) 0.6952(2) 0.0907(4) 0.0436(11) Uani 1 1 d . . . . .
H5 H 0.596150 0.677195 0.159099 0.052 Uiso 1 1 calc R . . . .
C1 C 0.6943(9) 0.5758(6) 0.8165(9) 0.152(5) Uani 1 1 d . . . . .
H1A H 0.622835 0.586110 0.770548 0.227 Uiso 1 1 calc GR . . . .
H1B H 0.724703 0.615951 0.879791 0.227 Uiso 1 1 calc GR . . . .
H1C H 0.701182 0.530120 0.869417 0.227 Uiso 1 1 calc GR . . . .
C2 C 0.7800(8) 0.3662(5) 0.6801(12) 0.152(5) Uani 1 1 d . . . . .
H2A H 0.711157 0.354131 0.623063 0.229 Uiso 1 1 calc GR . . . .
H2B H 0.798830 0.336400 0.764851 0.229 Uiso 1 1 calc GR . . . .
H2C H 0.826158 0.356196 0.627310 0.229 Uiso 1 1 calc GR . . . .
C3 C 0.7593(3) 0.5659(3) 0.4029(5) 0.0317(11) Uani 1 1 d . . . . .
C4 C 0.8292(4) 0.6275(3) 0.2266(5) 0.0405(12) Uani 1 1 d . . . . .
C5 C 0.9162(4) 0.6348(4) 0.1880(7) 0.0634(18) Uani 1 1 d . . . . .
H5A H 0.971824 0.602937 0.224723 0.076 Uiso 1 1 calc R . . . .
C6 C 0.9192(5) 0.6898(4) 0.0945(7) 0.077(2) Uani 1 1 d . . . . .
H6 H 0.978323 0.696978 0.069702 0.092 Uiso 1 1 calc R . . . .
C7 C 0.8360(4) 0.7344(4) 0.0372(7) 0.0649(18) Uani 1 1 d . . . . .
H7 H 0.836295 0.770997 -0.028989 0.078 Uiso 1 1 calc R . . . .
C8 C 0.7514(4) 0.7233(3) 0.0805(6) 0.0453(13) Uani 1 1 d . . . . .
C9 C 0.5670(4) 0.7566(3) 0.0215(6) 0.0457(13) Uani 1 1 d . . . . .
C10 C 0.3574(6) 0.7658(6) 0.1474(9) 0.116(3) Uani 1 1 d . . . . .
H10A H 0.401869 0.806000 0.141050 0.174 Uiso 1 1 calc GR . . . .
H10B H 0.384397 0.741736 0.238067 0.174 Uiso 1 1 calc GR . . . .
H10C H 0.290224 0.785057 0.137139 0.174 Uiso 1 1 calc GR . . . .
C11 C 0.3973(7) 0.5579(4) -0.1542(8) 0.112(3) Uani 1 1 d . . . . .
H11A H 0.374598 0.559485 -0.256150 0.169 Uiso 1 1 calc GR . . . .
H11B H 0.349313 0.529690 -0.122568 0.169 Uiso 1 1 calc GR . . . .
H11C H 0.463640 0.534757 -0.120689 0.169 Uiso 1 1 calc GR . . . .
O9 O 1.0059(3) 0.5267(3) 0.6588(5) 0.0755(13) Uani 1 1 d . U . . .
H9 H 0.945144 0.521644 0.612428 0.113 Uiso 1 1 calc GR . . . .
C12 C 1.0209(6) 0.5970(5) 0.7255(11) 0.115(3) Uani 1 1 d . U . . .
H12 H 0.955526 0.622361 0.713757 0.138 Uiso 1 1 calc R . . . .
C13 C 1.0867(8) 0.6403(6) 0.6558(12) 0.157(4) Uani 1 1 d . U . . .
H13A H 1.152689 0.616858 0.677222 0.235 Uiso 1 1 calc GR . . . .
H13B H 1.095156 0.690579 0.691200 0.235 Uiso 1 1 calc GR . . . .
H13C H 1.053938 0.640958 0.554829 0.235 Uiso 1 1 calc GR . . . .
C14 C 1.0767(9) 0.5826(7) 0.8754(13) 0.188(4) Uani 1 1 d . U . . .
H14A H 1.039047 0.547296 0.912336 0.282 Uiso 1 1 calc GR . . . .
H14B H 1.084225 0.628378 0.927989 0.282 Uiso 1 1 calc GR . . . .
H14C H 1.143233 0.562639 0.884143 0.282 Uiso 1 1 calc GR . . . .


_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 Na1 3.303(2) . ?
P1 O1 1.584(5) . ?
P1 O2 1.552(5) . ?
P1 O3 1.457(4) . ?
P1 N1 1.597(4) . ?
P2 O6 1.547(5) . ?
P2 O7 1.549(5) . ?
P2 O8 1.451(4) . ?
P2 N5 1.643(4) . ?
Na1 Na1 3.501(4) 3_666 ?
Na1 O3 2.374(4) . ?
Na1 O3 2.300(4) 3_666 ?
Na1 O4 2.399(3) . ?
Na1 O5 2.345(4) 4_576 ?
Na1 O8 2.265(4) . ?
O1 C1 1.389(8) . ?
O2 C2 1.367(10) . ?
O4 C3 1.241(5) . ?
O5 C9 1.227(6) . ?
O6 C10 1.418(8) . ?
O7 C11 1.346(8) . ?
N1 C3 1.327(6) . ?
N2 H2 0.8600 . ?
N2 C3 1.385(6) . ?
N2 C4 1.385(6) . ?
N3 C4 1.324(6) . ?
N3 C8 1.330(6) . ?
N4 H4 0.8600 . ?
N4 C8 1.382(6) . ?
N4 C9 1.350(6) . ?
N5 H5 0.8600 . ?
N5 C9 1.373(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C4 C5 1.373(7) . ?
C5 H5A 0.9300 . ?
C5 C6 1.364(8) . ?
C6 H6 0.9300 . ?
C6 C7 1.362(8) . ?
C7 H7 0.9300 . ?
C7 C8 1.375(7) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
O9 H9 0.8200 . ?
O9 C12 1.408(9) . ?
C12 H12 0.9800 . ?
C12 C13 1.514(12) . ?
C12 C14 1.465(13) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 Na1 92.4(2) . . ?
O1 P1 N1 105.0(3) . . ?
O2 P1 Na1 153.21(19) . . ?
O2 P1 O1 98.3(3) . . ?
O2 P1 N1 105.8(3) . . ?
O3 P1 Na1 39.79(15) . . ?
O3 P1 O1 112.1(3) . . ?
O3 P1 O2 113.6(2) . . ?
O3 P1 N1 119.6(2) . . ?
N1 P1 Na1 94.88(15) . . ?
O6 P2 O7 97.9(3) . . ?
O6 P2 N5 108.3(2) . . ?
O7 P2 N5 107.2(3) . . ?
O8 P2 O6 118.0(2) . . ?
O8 P2 O7 115.0(2) . . ?
O8 P2 N5 109.5(2) . . ?
P1 Na1 Na1 62.38(6) . 3_666 ?
O3 Na1 P1 23.13(9) . . ?
O3 Na1 P1 104.10(11) 3_666 . ?
O3 Na1 Na1 42.31(10) 3_666 3_666 ?
O3 Na1 Na1 40.69(9) . 3_666 ?
O3 Na1 O3 83.00(14) 3_666 . ?
O3 Na1 O4 79.16(13) . . ?
O3 Na1 O4 162.01(15) 3_666 . ?
O3 Na1 O5 102.35(15) 3_666 4_576 ?
O4 Na1 P1 58.77(9) . . ?
O4 Na1 Na1 119.82(12) . 3_666 ?
O5 Na1 P1 109.05(11) 4_576 . ?
O5 Na1 Na1 121.13(14) 4_576 3_666 ?
O5 Na1 O3 123.73(16) 4_576 . ?
O5 Na1 O4 89.54(14) 4_576 . ?
O8 Na1 P1 137.51(12) . . ?
O8 Na1 Na1 130.85(13) . 3_666 ?
O8 Na1 O3 137.90(16) . . ?
O8 Na1 O3 103.28(14) . 3_666 ?
O8 Na1 O4 88.63(13) . . ?
O8 Na1 O5 95.97(15) . 4_576 ?
C1 O1 P1 122.8(5) . . ?
C2 O2 P1 121.3(6) . . ?
P1 O3 Na1 117.1(2) . . ?
P1 O3 Na1 138.7(2) . 3_666 ?
Na1 O3 Na1 97.00(14) 3_666 . ?
C3 O4 Na1 131.8(3) . . ?
C9 O5 Na1 130.8(3) . 4_575 ?
C10 O6 P2 121.2(4) . . ?
C11 O7 P2 128.1(5) . . ?
P2 O8 Na1 138.1(2) . . ?
C3 N1 P1 119.7(3) . . ?
C3 N2 H2 115.3 . . ?
C3 N2 C4 129.4(4) . . ?
C4 N2 H2 115.3 . . ?
C4 N3 C8 118.6(4) . . ?
C8 N4 H4 114.5 . . ?
C9 N4 H4 114.5 . . ?
C9 N4 C8 130.9(5) . . ?
P2 N5 H5 117.1 . . ?
C9 N5 P2 125.8(4) . . ?
C9 N5 H5 117.1 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
O2 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O4 C3 N1 127.8(4) . . ?
O4 C3 N2 120.0(4) . . ?
N1 C3 N2 112.1(4) . . ?
N3 C4 N2 118.8(4) . . ?
N3 C4 C5 122.2(5) . . ?
C5 C4 N2 118.9(5) . . ?
C4 C5 H5A 120.8 . . ?
C6 C5 C4 118.4(5) . . ?
C6 C5 H5A 120.8 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.4(5) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 121.1 . . ?
C6 C7 C8 117.8(5) . . ?
C8 C7 H7 121.1 . . ?
N3 C8 N4 117.6(4) . . ?
N3 C8 C7 122.7(5) . . ?
C7 C8 N4 119.8(5) . . ?
O5 C9 N4 120.1(5) . . ?
O5 C9 N5 122.3(5) . . ?
N4 C9 N5 117.6(5) . . ?
O6 C10 H10A 109.5 . . ?
O6 C10 H10B 109.5 . . ?
O6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O7 C11 H11A 109.5 . . ?
O7 C11 H11B 109.5 . . ?
O7 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 O9 H9 109.5 . . ?
O9 C12 H12 111.5 . . ?
O9 C12 C13 105.3(8) . . ?
O9 C12 C14 105.7(9) . . ?
C13 C12 H12 111.5 . . ?
C14 C12 H12 111.5 . . ?
C14 C12 C13 111.1(9) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
_geom_hbond_publ_flag
N2 H2 O9 0.86 2.04 2.885(5) 166.5 3_766 yes
N4 H4 O4 0.86 2.00 2.857(5) 170.6 4_575 yes
N5 H5 N3 0.86 2.05 2.663(5) 127.9 . yes
O9 H9 N1 0.82 2.02 2.834(5) 174.6 . yes

_olex2_submission_special_instructions 'No special instructions were received'
