#------------------------------------------------------------------------------
#$Date: 2021-04-05 17:42:55 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263741 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/66/7706613.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7706613
loop_
_publ_author_name
'Zhang, Jianfeng'
'Wenzel, Marco'
'Schnaars, Kathleen'
'Hennersdorf, Felix'
'Schwedtmann, Kai'
'März, Juliane'
'Rossberg, André'
'Kaden, Peter'
'Kraus, Florian'
'Stumpf, Thorsten'
'Weigand, Jan J.'
_publ_section_title
;
 Coordination of trivalent lanthanum and cerium, and tetravalent cerium
 and actinides (An = Th(IV), U(IV), Np(IV)) by a 4-phosphoryl
 1H-pyrazol-5-olate ligand in solution and the solid state.
;
_journal_issue                   10
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3550
_journal_page_last               3558
_journal_paper_doi               10.1039/d1dt00365h
_journal_volume                  50
_journal_year                    2021
_chemical_formula_moiety
'C68 H96 N8 Np O16 P4, 3(C2 H3 N), 2(H3 O1.5)'
_chemical_formula_sum            'C74 H111 N11 Np O19 P4'
_chemical_formula_weight         1819.61
_space_group_crystal_system      tetragonal
_space_group_IT_number           85
_space_group_name_Hall           '-P 4a'
_space_group_name_H-M_alt        'P 4/n :2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-11-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2020-04-08 deposited with the CCDC.	2021-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   17.6551(7)
_cell_length_b                   17.6551(7)
_cell_length_c                   13.7559(6)
_cell_measurement_reflns_used    7710
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.4569
_cell_measurement_theta_min      2.2210
_cell_volume                     4287.7(3)
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0083
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            99347
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         2.307
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    1.357
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0661 before and 0.0428 after correction. The Ratio of minimum to maximum transmission is 0.9449. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       block
_exptl_crystal_F_000             1874
_exptl_crystal_size_max          0.334
_exptl_crystal_size_mid          0.324
_exptl_crystal_size_min          0.278
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         4740
_refine_ls_number_restraints     77
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0161
_refine_ls_R_factor_gt           0.0152
_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)+(0.0189P)²+2.1268P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0388
_refine_ls_wR_factor_ref         0.0394
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4599
_reflns_number_total             4740
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt00365h2.cif
_cod_data_source_block           6_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7706609--7706617.cif.'
_cod_original_cell_volume        4287.7(4)
_cod_original_sg_symbol_H-M      'P 4/n'
_cod_database_code               7706613
_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.
;
_shelx_estimated_absorpt_t_max   0.704
_shelx_estimated_absorpt_t_min   0.660
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H5A,H5B} of O6
 At 1.5 times of:
  All C(H,H,H) groups, {H6A,H6B} of O6, All C(H,H,H,H,H,H) groups
2. Restrained distances
 O5-H5B = O5-H5A
 0.87 with sigma of 0.001
 C18-H18C_$1 = C18-H18A_$1 = C18-H18B_$1
 0.96 with sigma of 0.001
 H18B-H18A \\sim H18A-H18C \\sim H18B-H18C
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
N4 \\sim C20 \\sim C21 \\sim N5 \\sim C23 \\sim C22: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
4. Same fragment restrains
{N4, C21, C20} sigma for 1-2: 0.02, 1-3: 0.02
as
{N5, C23, C22}
5. Others
 Fixed Sof: N5(0.25) C23(0.25) C22(0.25) H22A(0.25) H22B(0.25) H22C(0.25)
 H18A(0.25) H18B(0.25) H18C(0.25) N4(0.25) C21(0.25) C20(0.25) H20A(0.25)
 H20B(0.25) H20C(0.25) O5(0.5) O6(0.25) H6A(0.25) H6B(0.25) H5A(0.5) H5B(0.5)
6.a Free rotating group:
 O6(H6A,H6B)
6.b Ternary CH refined with riding coordinates:
 C12(H12), C15(H15)
6.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10)
6.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C22(H22A,H22B,H22C), C20(H20A,
 H20B,H20C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y+1/2, x, z'
'y, -x+1/2, z'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y-1/2, -x, -z'
'-y, x-1/2, -z'
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
C1 C 0.42658(7) 0.27153(7) 0.46443(10) 0.0164(2) Uani 1 1 d . . . . .
C2 C 0.46174(7) 0.31472(7) 0.39165(10) 0.0195(3) Uani 1 1 d . . . . .
C3 C 0.53740(8) 0.32506(8) 0.42411(13) 0.0267(3) Uani 1 1 d . . . . .
C4 C 0.59946(9) 0.36505(10) 0.37124(15) 0.0400(4) Uani 1 1 d . . . . .
H4A H 0.6085 0.3400 0.3087 0.060 Uiso 1 1 calc GR . . . .
H4B H 0.6458 0.3635 0.4103 0.060 Uiso 1 1 calc GR . . . .
H4C H 0.5848 0.4179 0.3600 0.060 Uiso 1 1 calc GR . . . .
C5 C 0.47408(8) 0.22107(8) 0.62365(10) 0.0203(3) Uani 1 1 d . . . . .
C6 C 0.42478(8) 0.15967(8) 0.63322(10) 0.0226(3) Uani 1 1 d . . . . .
H6 H 0.3943 0.1441 0.5799 0.027 Uiso 1 1 calc R . . . .
C7 C 0.42074(8) 0.12164(9) 0.72105(11) 0.0264(3) Uani 1 1 d . . . . .
H7 H 0.3866 0.0804 0.7276 0.032 Uiso 1 1 calc R . . . .
C8 C 0.46545(9) 0.14241(9) 0.79990(11) 0.0298(3) Uani 1 1 d . . . . .
C9 C 0.51359(9) 0.20390(9) 0.78910(11) 0.0312(3) Uani 1 1 d . . . . .
H9 H 0.5442 0.2192 0.8423 0.037 Uiso 1 1 calc R . . . .
C10 C 0.51794(8) 0.24344(8) 0.70225(11) 0.0265(3) Uani 1 1 d . . . . .
H10 H 0.5509 0.2858 0.6965 0.032 Uiso 1 1 calc R . . . .
C11 C 0.46151(14) 0.09849(13) 0.89369(12) 0.0489(5) Uani 1 1 d . . . . .
H11A H 0.4098 0.1006 0.9195 0.073 Uiso 1 1 calc GR . . . .
H11B H 0.4966 0.1207 0.9410 0.073 Uiso 1 1 calc GR . . . .
H11C H 0.4756 0.0456 0.8816 0.073 Uiso 1 1 calc GR . . . .
C12 C 0.45003(10) 0.31945(10) 0.09927(12) 0.0333(3) Uani 1 1 d . . . . .
H12 H 0.4237 0.3693 0.0923 0.040 Uiso 1 1 calc R . . . .
C13 C 0.40028(13) 0.25742(12) 0.06089(16) 0.0515(5) Uani 1 1 d . . . . .
H13A H 0.3895 0.2666 -0.0080 0.077 Uiso 1 1 calc GR . . . .
H13B H 0.3527 0.2565 0.0975 0.077 Uiso 1 1 calc GR . . . .
H13C H 0.4262 0.2086 0.0680 0.077 Uiso 1 1 calc GR . . . .
C14 C 0.52653(13) 0.32312(14) 0.05153(15) 0.0551(5) Uani 1 1 d . . . . .
H14A H 0.5202 0.3321 -0.0183 0.083 Uiso 1 1 calc GR . . . .
H14B H 0.5532 0.2751 0.0616 0.083 Uiso 1 1 calc GR . . . .
H14C H 0.5560 0.3645 0.0802 0.083 Uiso 1 1 calc GR . . . .
C15 C 0.38476(9) 0.48874(8) 0.30650(14) 0.0321(4) Uani 1 1 d . . . . .
H15 H 0.3330 0.4684 0.3200 0.038 Uiso 1 1 calc R . . . .
C16 C 0.42049(15) 0.51413(11) 0.39992(14) 0.0529(6) Uani 1 1 d . . . . .
H16A H 0.4712 0.5342 0.3867 0.079 Uiso 1 1 calc GR . . . .
H16B H 0.4243 0.4710 0.4445 0.079 Uiso 1 1 calc GR . . . .
H16C H 0.3893 0.5538 0.4295 0.079 Uiso 1 1 calc GR . . . .
C17 C 0.37949(11) 0.55124(9) 0.23257(15) 0.0425(4) Uani 1 1 d . . . . .
H17A H 0.4302 0.5712 0.2193 0.064 Uiso 1 1 calc GR . . . .
H17B H 0.3473 0.5919 0.2579 0.064 Uiso 1 1 calc GR . . . .
H17C H 0.3575 0.5313 0.1723 0.064 Uiso 1 1 calc GR . . . .
N1 N 0.48070(6) 0.25967(6) 0.53405(9) 0.0216(2) Uani 1 1 d . . . . .
N2 N 0.54932(7) 0.29314(7) 0.50898(11) 0.0297(3) Uani 1 1 d . . . . .
Np1 Np 0.2500 0.2500 0.38117(2) 0.01200(4) Uani 1 4 d S T P . .
O1 O 0.35932(5) 0.24474(5) 0.47169(7) 0.01668(18) Uani 1 1 d . . . . .
O2 O 0.33556(5) 0.32369(5) 0.28718(7) 0.01862(18) Uani 1 1 d . . . . .
O3 O 0.46451(6) 0.30406(6) 0.20239(8) 0.0260(2) Uani 1 1 d . . . . .
O4 O 0.43157(5) 0.42910(5) 0.26268(8) 0.0231(2) Uani 1 1 d . . . . .
P1 P 0.41806(2) 0.34280(2) 0.28539(3) 0.01836(7) Uani 1 1 d . . . . .
N5 N 0.3317(5) 0.7872(6) 0.0492(7) 0.078(2) Uani 0.25 1 d D U . A -2
C23 C 0.2877(6) 0.7636(7) 0.1015(7) 0.059(2) Uani 0.25 1 d D U . A -2
C22 C 0.248(2) 0.7389(18) 0.1743(14) 0.067(5) Uani 0.25 1 d D U . A -2
H22A H 0.2357 0.6854 0.1640 0.101 Uiso 0.25 1 calc GR . . A -2
H22B H 0.2013 0.7683 0.1797 0.101 Uiso 0.25 1 calc GR . . A -2
H22C H 0.2776 0.7442 0.2344 0.101 Uiso 0.25 1 calc GR . . A -2
H18A H 0.235(4) 0.2026(15) 0.664(5) 0.101 Uiso 0.25 1 d DR . . B -1
H18B H 0.3024(11) 0.258(4) 0.677(6) 0.101 Uiso 0.25 1 d DR . . C -1
H18C H 0.221(3) 0.290(2) 0.662(4) 0.101 Uiso 0.25 1 d DR . . D -1
C18 C 0.2500 0.2500 0.6922(3) 0.0357(7) Uani 1 4 d DS T P . .
C19 C 0.2500 0.2500 0.7939(3) 0.0659(13) Uani 1 4 d S T P . .
N3 N 0.2500 0.2500 0.8747(4) 0.179(4) Uani 1 4 d S T P . .
N4 N 0.3132(5) 0.6664(6) 0.0570(7) 0.075(2) Uani 0.25 1 d D U . E -1
C21 C 0.2866(6) 0.7092(6) 0.1099(7) 0.057(2) Uani 0.25 1 d D U . E -1
C20 C 0.2742(13) 0.7634(15) 0.1705(16) 0.077(4) Uani 0.25 1 d D U . E -1
H20A H 0.2242 0.7854 0.1578 0.115 Uiso 0.25 1 calc GR . . E -1
H20B H 0.3131 0.8025 0.1627 0.115 Uiso 0.25 1 calc GR . . E -1
H20C H 0.2757 0.7436 0.2370 0.115 Uiso 0.25 1 calc GR . . E -1
O5 O 0.69203(14) 0.30468(16) 0.6202(2) 0.0348(6) Uani 0.5 1 d D . . . .
O6 O 0.7957(3) 0.1985(3) 0.5575(5) 0.0494(15) Uani 0.25 1 d . . . . .
H6A H 0.7756 0.1546 0.5444 0.074 Uiso 0.25 1 d G . . . .
H6B H 0.8438 0.1974 0.5440 0.074 Uiso 0.25 1 d G . . . .
H5A H 0.6500 0.2957 0.5893 0.059 Uiso 0.5 1 d DR . . . .
H5B H 0.7261 0.2696 0.6120 0.059 Uiso 0.5 1 d DR . . . .
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'
Np Np -11.4937 4.1493 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 105.88(11) . . ?
O1 C1 C2 131.74(12) . . ?
O1 C1 N1 122.38(12) . . ?
C1 C2 C3 105.17(12) . . ?
C1 C2 P1 124.26(10) . . ?
C3 C2 P1 130.52(11) . . ?
C2 C3 C4 126.74(15) . . ?
N2 C3 C2 112.03(12) . . ?
N2 C3 C4 121.22(13) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N1 120.54(12) . . ?
C10 C5 C6 119.70(13) . . ?
C10 C5 N1 119.75(13) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 C5 119.40(13) . . ?
C7 C6 H6 120.3 . . ?
C6 C7 H7 119.2 . . ?
C6 C7 C8 121.58(14) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 C11 120.39(16) . . ?
C9 C8 C7 118.08(15) . . ?
C9 C8 C11 121.53(16) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.38(14) . . ?
C10 C9 H9 119.3 . . ?
C5 C10 H10 120.1 . . ?
C9 C10 C5 119.84(14) . . ?
C9 C10 H10 120.1 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 H12 109.7 . . ?
C13 C12 C14 113.82(17) . . ?
C14 C12 H12 109.7 . . ?
O3 C12 H12 109.7 . . ?
O3 C12 C13 107.89(14) . . ?
O3 C12 C14 105.90(15) . . ?
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 . . ?
C16 C15 H15 109.4 . . ?
C16 C15 C17 112.71(14) . . ?
C17 C15 H15 109.4 . . ?
O4 C15 H15 109.4 . . ?
O4 C15 C16 109.24(14) . . ?
O4 C15 C17 106.47(13) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C1 N1 C5 128.77(11) . . ?
C1 N1 N2 111.67(11) . . ?
N2 N1 C5 119.54(11) . . ?
C3 N2 N1 105.25(11) . . ?
O1 Np1 O1 72.94(2) 3 . ?
O1 Np1 O1 72.94(2) 4 2 ?
O1 Np1 O1 72.94(2) 4 . ?
O1 Np1 O1 114.40(4) 3 4 ?
O1 Np1 O1 72.94(2) 3 2 ?
O1 Np1 O1 114.40(4) 2 . ?
O1 Np1 O2 141.27(3) 4 . ?
O1 Np1 O2 141.27(3) 3 2 ?
O1 Np1 O2 141.27(3) 2 4 ?
O1 Np1 O2 79.01(3) . 4 ?
O1 Np1 O2 79.01(3) 3 . ?
O1 Np1 O2 141.27(3) . 3 ?
O1 Np1 O2 143.75(3) . 2 ?
O1 Np1 O2 77.47(3) 2 2 ?
O1 Np1 O2 77.47(3) . . ?
O1 Np1 O2 77.47(3) 4 4 ?
O1 Np1 O2 143.75(3) 4 3 ?
O1 Np1 O2 143.75(3) 2 . ?
O1 Np1 O2 143.75(3) 3 4 ?
O1 Np1 O2 77.47(3) 3 3 ?
O1 Np1 O2 79.01(3) 4 2 ?
O1 Np1 O2 79.01(3) 2 3 ?
O2 Np1 O2 72.78(2) 2 4 ?
O2 Np1 O2 72.78(2) 2 3 ?
O2 Np1 O2 114.07(5) 2 . ?
O2 Np1 O2 72.78(2) 4 . ?
O2 Np1 O2 72.78(2) 3 . ?
O2 Np1 O2 114.07(5) 4 3 ?
C1 O1 Np1 136.10(8) . . ?
P1 O2 Np1 138.75(5) . . ?
C12 O3 P1 122.27(10) . . ?
C15 O4 P1 121.84(8) . . ?
O2 P1 C2 110.89(6) . . ?
O2 P1 O3 115.10(6) . . ?
O2 P1 O4 111.68(5) . . ?
O3 P1 C2 104.99(6) . . ?
O3 P1 O4 101.48(5) . . ?
O4 P1 C2 112.25(6) . . ?
N5 C23 C22 168.3(18) . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
C23 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
H18A C18 H18B 108(2) . . ?
H18A C18 H18C 108(2) . . ?
H18B C18 H18C 108(2) . . ?
C19 C18 H18A 114(4) . . ?
C19 C18 H18B 103(5) . . ?
C19 C18 H18C 115(4) . . ?
N3 C19 C18 180.0 . . ?
N4 C21 C20 165.5(15) . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O6 O5 H5A 73.9 2_655 . ?
O6 O5 H5B 70.2 2_655 . ?
H5A O5 H5B 113.3 . . ?
O5 O6 H6A 104.1 2_655 . ?
O5 O6 H6B 88.2 2_655 . ?
H6A O6 H6B 109.5 . . ?
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
C1 C2 1.4032(18) . ?
C1 N1 1.3689(17) . ?
C1 O1 1.2821(15) . ?
C2 C3 1.4202(19) . ?
C2 P1 1.7254(14) . ?
C3 C4 1.493(2) . ?
C3 N2 1.313(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.396(2) . ?
C5 C10 1.3873(19) . ?
C5 N1 1.4132(18) . ?
C6 H6 0.9500 . ?
C6 C7 1.384(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.391(2) . ?
C8 C9 1.387(2) . ?
C8 C11 1.507(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(2) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12 1.0000 . ?
C12 C13 1.500(3) . ?
C12 C14 1.503(2) . ?
C12 O3 1.4667(19) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15 1.0000 . ?
C15 C16 1.500(3) . ?
C15 C17 1.504(2) . ?
C15 O4 1.4680(17) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
N1 N2 1.3914(16) . ?
Np1 O1 2.2988(9) 3 ?
Np1 O1 2.2988(9) . ?
Np1 O1 2.2988(9) 2 ?
Np1 O1 2.2988(9) 4 ?
Np1 O2 2.3761(9) 4 ?
Np1 O2 2.3761(9) 2 ?
Np1 O2 2.3761(9) 3 ?
Np1 O2 2.3761(9) . ?
O2 P1 1.4953(9) . ?
O3 P1 1.5632(10) . ?
O4 P1 1.5735(9) . ?
N5 C23 1.138(11) . ?
C23 C22 1.296(17) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C18 H18A 0.9600(10) . ?
C18 H18B 0.9600(11) . ?
C18 H18C 0.9600(10) . ?
C18 C19 1.399(5) . ?
C19 N3 1.112(7) . ?
N4 C21 1.149(11) . ?
C21 C20 1.288(17) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O5 O6 0.892(7) 2_655 ?
O5 H5A 0.8700 . ?
O5 H5B 0.8700 . ?
O6 O5 0.892(7) 2_655 ?
O6 H6A 0.8698 . ?
O6 H6B 0.8699 . ?
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
C1 C2 C3 C4 177.72(15) . . . . ?
C1 C2 C3 N2 -0.89(17) . . . . ?
C1 C2 P1 O2 7.31(14) . . . . ?
C1 C2 P1 O3 -117.60(12) . . . . ?
C1 C2 P1 O4 133.00(11) . . . . ?
C1 N1 N2 C3 -0.31(16) . . . . ?
C2 C1 N1 C5 178.26(13) . . . . ?
C2 C1 N1 N2 -0.24(15) . . . . ?
C2 C1 O1 Np1 -2.9(2) . . . . ?
C2 C3 N2 N1 0.74(17) . . . . ?
C3 C2 P1 O2 -175.85(13) . . . . ?
C3 C2 P1 O3 59.25(15) . . . . ?
C3 C2 P1 O4 -50.16(15) . . . . ?
C4 C3 N2 N1 -177.96(14) . . . . ?
C5 C6 C7 C8 -0.9(2) . . . . ?
C5 N1 N2 C3 -178.96(12) . . . . ?
C6 C5 C10 C9 1.2(2) . . . . ?
C6 C5 N1 C1 32.2(2) . . . . ?
C6 C5 N1 N2 -149.45(13) . . . . ?
C6 C7 C8 C9 1.4(2) . . . . ?
C6 C7 C8 C11 -178.17(15) . . . . ?
C7 C8 C9 C10 -0.6(2) . . . . ?
C8 C9 C10 C5 -0.7(2) . . . . ?
C10 C5 C6 C7 -0.4(2) . . . . ?
C10 C5 N1 C1 -149.05(14) . . . . ?
C10 C5 N1 N2 29.34(18) . . . . ?
C11 C8 C9 C10 178.97(16) . . . . ?
C12 O3 P1 C2 -174.03(11) . . . . ?
C12 O3 P1 O2 63.76(12) . . . . ?
C12 O3 P1 O4 -57.00(12) . . . . ?
C13 C12 O3 P1 -97.52(15) . . . . ?
C14 C12 O3 P1 140.25(13) . . . . ?
C15 O4 P1 C2 -83.43(13) . . . . ?
C15 O4 P1 O2 41.83(13) . . . . ?
C15 O4 P1 O3 164.96(12) . . . . ?
C16 C15 O4 P1 90.66(14) . . . . ?
C17 C15 O4 P1 -147.36(11) . . . . ?
N1 C1 C2 C3 0.64(14) . . . . ?
N1 C1 C2 P1 178.16(10) . . . . ?
N1 C1 O1 Np1 178.16(8) . . . . ?
N1 C5 C6 C7 178.39(13) . . . . ?
N1 C5 C10 C9 -177.62(13) . . . . ?
Np1 O2 P1 C2 -12.19(10) . . . . ?
Np1 O2 P1 O3 106.78(9) . . . . ?
Np1 O2 P1 O4 -138.20(8) . . . . ?
O1 C1 C2 C3 -178.38(13) . . . . ?
O1 C1 C2 P1 -0.9(2) . . . . ?
O1 C1 N1 C5 -2.6(2) . . . . ?
O1 C1 N1 N2 178.90(12) . . . . ?
P1 C2 C3 C4 0.4(2) . . . . ?
P1 C2 C3 N2 -178.19(11) . . . . ?
