#------------------------------------------------------------------------------
#$Date: 2021-07-05 20:05:29 +0200 (lun 05 de jul de 2021) $
#$Revision: 267219 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/06/7060697.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_7060697
loop_
_publ_author_name
'Hkiri, Shaima'
'Gourlaouen, Christophe'
'Touil, Soufiane'
'Samarat, Ali'
'Sémeril, David'
_publ_section_title
;
 1,3,4-Oxadiazole-functionalized α-amino-phosphonates as ligands for the
 ruthenium-catalyzed reduction of ketones
;
_journal_issue                   25
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              11327
_journal_page_last               11335
_journal_paper_doi               10.1039/D1NJ01861B
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C20 H24 N3 O5 P'
_chemical_formula_sum            'C20 H24 N3 O5 P'
_chemical_formula_weight         417.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-04-08 deposited with the CCDC.	2021-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                90.816(4)
_cell_angle_beta                 94.235(4)
_cell_angle_gamma                103.384(4)
_cell_formula_units_Z            4
_cell_length_a                   8.8977(11)
_cell_length_b                   12.5369(14)
_cell_length_c                   19.514(2)
_cell_measurement_reflns_used    9170
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.73
_cell_measurement_theta_min      2.51
_cell_volume                     2110.8(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker PHOTON-III CPAD'
_diffrn_measurement_method       'φ and ω shuterless scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0806
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            98599
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.012
_diffrn_reflns_theta_min         2.094
_diffrn_source                   'Mo-ImuS 3.0 microfocus tube'
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       prism
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.677
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     538
_refine_ls_number_reflns         10141
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0823
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0942P)²+8.1397P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2225
_refine_ls_wR_factor_ref         0.2412
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8283
_reflns_number_total             10141
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj01861b2.cif
_cod_data_source_block           dsds200724
_cod_depositor_comments
'Adding full bibliography for 7060696--7060698.cif.'
_cod_database_code               7060697
_shelx_shelxl_version_number     2014/7
_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_min   0.964
_shelx_estimated_absorpt_t_max   0.971
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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 0.2934(5) 0.9603(3) -0.0235(2) 0.0281(8) Uani 1 1 d . . . . .
C2 C 0.3686(5) 0.9654(3) -0.0839(2) 0.0307(9) Uani 1 1 d . . . . .
H2 H 0.4182 0.9090 -0.0957 0.037 Uiso 1 1 calc R U . . .
C3 C 0.3710(5) 1.0534(4) -0.1269(3) 0.0340(10) Uani 1 1 d . . . . .
H3 H 0.4209 1.0563 -0.1685 0.041 Uiso 1 1 calc R U . . .
C4 C 0.3016(6) 1.1360(4) -0.1097(3) 0.0372(10) Uani 1 1 d . . . . .
H4 H 0.3059 1.1966 -0.1387 0.045 Uiso 1 1 calc R U . . .
C5 C 0.2256(6) 1.1312(4) -0.0503(3) 0.0417(11) Uani 1 1 d . . . . .
H5 H 0.1761 1.1879 -0.0391 0.050 Uiso 1 1 calc R U . . .
C6 C 0.2208(6) 1.0443(4) -0.0067(3) 0.0370(10) Uani 1 1 d . . . . .
H6 H 0.1689 1.0417 0.0343 0.044 Uiso 1 1 calc R U . . .
C7 C 0.2932(5) 0.8714(3) 0.0241(2) 0.0267(8) Uani 1 1 d . . . . .
C8 C 0.3436(5) 0.7236(3) 0.0612(2) 0.0247(8) Uani 1 1 d . . . . .
C9 C 0.3750(5) 0.5629(3) 0.1195(2) 0.0239(8) Uani 1 1 d . . . . .
H9 H 0.3750 0.6097 0.1614 0.029 Uiso 1 1 calc R U . . .
C10 C 0.2225(5) 0.4768(3) 0.1126(2) 0.0266(8) Uani 1 1 d . . . . .
C11 C 0.1548(5) 0.4301(4) 0.0496(2) 0.0313(9) Uani 1 1 d . . . . .
H11 H 0.2012 0.4552 0.0087 0.038 Uiso 1 1 calc R U . . .
C12 C 0.0199(6) 0.3473(4) 0.0455(3) 0.0389(10) Uani 1 1 d . . . . .
H12 H -0.0258 0.3158 0.0021 0.047 Uiso 1 1 calc R U . . .
C13 C -0.0470(6) 0.3111(4) 0.1053(3) 0.0414(11) Uani 1 1 d . . . . .
H13 H -0.1385 0.2538 0.1028 0.050 Uiso 1 1 calc R U . . .
C14 C 0.0183(5) 0.3578(4) 0.1692(3) 0.0355(10) Uani 1 1 d . . . . .
H14 H -0.0283 0.3325 0.2100 0.043 Uiso 1 1 calc R U . . .
C15 C 0.1525(5) 0.4420(4) 0.1727(2) 0.0288(8) Uani 1 1 d . . . . .
C16 C 0.1615(6) 0.4567(5) 0.2949(3) 0.0418(11) Uani 1 1 d . . . . .
H16A H 0.0554 0.4665 0.2954 0.063 Uiso 1 1 calc R U . . .
H16B H 0.2260 0.4986 0.3336 0.063 Uiso 1 1 calc R U . . .
H16C H 0.1607 0.3788 0.2989 0.063 Uiso 1 1 calc R U . . .
C17 C 0.8032(6) 0.5698(4) 0.2075(3) 0.0410(11) Uani 1 1 d . . . . .
H17A H 0.8029 0.4907 0.2069 0.049 Uiso 1 1 calc R U . . .
H17B H 0.8267 0.5983 0.2556 0.049 Uiso 1 1 calc R U . . .
C18 C 0.9245(6) 0.6288(5) 0.1645(4) 0.0508(14) Uani 1 1 d . . . . .
H18A H 0.9131 0.5914 0.1193 0.076 Uiso 1 1 calc R U . . .
H18B H 1.0271 0.6299 0.1869 0.076 Uiso 1 1 calc R U . . .
H18C H 0.9135 0.7043 0.1588 0.076 Uiso 1 1 calc R U . . .
C19 C 0.4285(7) 0.2847(4) 0.1475(3) 0.0431(12) Uani 1 1 d . . . . .
H19A H 0.3245 0.2786 0.1237 0.052 Uiso 1 1 calc R U . . .
H19B H 0.4988 0.2701 0.1133 0.052 Uiso 1 1 calc R U . . .
C20 C 0.4197(9) 0.2056(5) 0.2020(3) 0.0586(16) Uani 1 1 d . . . . .
H20A H 0.5239 0.2097 0.2237 0.088 Uiso 1 1 calc R U . . .
H20B H 0.3763 0.1315 0.1824 0.088 Uiso 1 1 calc R U . . .
H20C H 0.3532 0.2224 0.2364 0.088 Uiso 1 1 calc R U . . .
C21 C 0.3048(5) 0.4593(3) 0.5373(2) 0.0284(8) Uani 1 1 d . . . . .
C22 C 0.4102(6) 0.4710(4) 0.5949(2) 0.0324(9) Uani 1 1 d . . . . .
H22 H 0.4702 0.4181 0.6025 0.039 Uiso 1 1 calc R U . . .
C23 C 0.4290(6) 0.5588(4) 0.6412(3) 0.0359(10) Uani 1 1 d . . . . .
H23 H 0.5015 0.5661 0.6802 0.043 Uiso 1 1 calc R U . . .
C24 C 0.3407(7) 0.6360(4) 0.6300(3) 0.0488(13) Uani 1 1 d . . . . .
H24 H 0.3506 0.6953 0.6621 0.059 Uiso 1 1 calc R U . . .
C25 C 0.2394(9) 0.6264(5) 0.5726(4) 0.068(2) Uani 1 1 d . . . . .
H25 H 0.1830 0.6813 0.5642 0.081 Uiso 1 1 calc R U . . .
C26 C 0.2177(7) 0.5375(5) 0.5263(3) 0.0489(14) Uani 1 1 d . . . . .
H26 H 0.1442 0.5303 0.4877 0.059 Uiso 1 1 calc R U . . .
C27 C 0.2839(5) 0.3675(3) 0.4885(2) 0.0265(8) Uani 1 1 d . . . . .
C28 C 0.3231(5) 0.2199(3) 0.4458(2) 0.0260(8) Uani 1 1 d . . . . .
C29 C 0.3472(5) 0.0629(3) 0.3800(2) 0.0275(8) Uani 1 1 d . . . . .
H29 H 0.3354 0.1091 0.3395 0.033 Uiso 1 1 calc R U . . .
C30 C 0.1981(5) -0.0255(4) 0.3823(2) 0.0307(9) Uani 1 1 d . . . . .
C31 C 0.1595(6) -0.0779(4) 0.4423(3) 0.0398(11) Uani 1 1 d . . . . .
H31 H 0.2232 -0.0555 0.4836 0.048 Uiso 1 1 calc R U . . .
C32 C 0.0277(7) -0.1639(5) 0.4431(3) 0.0537(15) Uani 1 1 d . . . . .
H32 H 0.0002 -0.1988 0.4848 0.064 Uiso 1 1 calc R U . . .
C33 C -0.0612(6) -0.1968(5) 0.3828(3) 0.0507(14) Uani 1 1 d . . . . .
H33 H -0.1494 -0.2563 0.3831 0.061 Uiso 1 1 calc R U . . .
C34 C -0.0269(6) -0.1464(4) 0.3218(3) 0.0417(11) Uani 1 1 d . . . . .
H34 H -0.0902 -0.1709 0.2807 0.050 Uiso 1 1 calc R U . . .
C35 C 0.1030(5) -0.0585(4) 0.3214(2) 0.0340(9) Uani 1 1 d . . . . .
C36 C 0.0520(6) -0.0293(5) 0.2019(3) 0.0459(12) Uani 1 1 d . . . . .
H36A H 0.0450 -0.1064 0.1895 0.069 Uiso 1 1 calc R U . . .
H36B H 0.0980 0.0172 0.1654 0.069 Uiso 1 1 calc R U . . .
H36C H -0.0519 -0.0185 0.2078 0.069 Uiso 1 1 calc R U . . .
C37 C 0.7938(6) 0.0774(5) 0.3441(3) 0.0474(14) Uani 1 1 d . . . . .
H37A H 0.7885 0.0020 0.3266 0.057 Uiso 1 1 calc R U . . .
H37B H 0.8495 0.0871 0.3905 0.057 Uiso 1 1 calc R U . . .
C38 C 0.8766(6) 0.1579(4) 0.2975(3) 0.0420(11) Uani 1 1 d . . . . .
H38A H 0.8227 0.1461 0.2514 0.063 Uiso 1 1 calc R U . . .
H38B H 0.9827 0.1490 0.2955 0.063 Uiso 1 1 calc R U . . .
H38C H 0.8793 0.2323 0.3146 0.063 Uiso 1 1 calc R U . . .
C39 C 0.3857(6) -0.1902(4) 0.2954(3) 0.0430(11) Uani 1 1 d . . . . .
H39A H 0.3082 -0.2077 0.2553 0.052 Uiso 1 1 calc R U . . .
H39B H 0.3317 -0.2102 0.3375 0.052 Uiso 1 1 calc R U . . .
C40 C 0.5064(7) -0.2537(4) 0.2893(3) 0.0464(12) Uani 1 1 d . . . . .
H40A H 0.5590 -0.2339 0.2474 0.070 Uiso 1 1 calc R U . . .
H40B H 0.4576 -0.3324 0.2873 0.070 Uiso 1 1 calc R U . . .
H40C H 0.5821 -0.2367 0.3294 0.070 Uiso 1 1 calc R U . . .
N1 N 0.2401(5) 0.8588(3) 0.0831(2) 0.0323(8) Uani 1 1 d . . . . .
N2 N 0.2713(4) 0.7602(3) 0.1089(2) 0.0304(8) Uani 1 1 d . . . . .
N3 N 0.4042(4) 0.6350(3) 0.0617(2) 0.0252(7) Uani 1 1 d . . . . .
N4 N 0.1960(5) 0.3462(3) 0.4326(2) 0.0307(8) Uani 1 1 d . . . . .
N5 N 0.2199(4) 0.2475(3) 0.40369(19) 0.0296(8) Uani 1 1 d . . . . .
N6 N 0.3915(4) 0.1351(3) 0.4408(2) 0.0284(7) Uani 1 1 d . . . . .
O1 O 0.3625(3) 0.7883(2) 0.00540(15) 0.0246(6) Uani 1 1 d . . . . .
O2 O 0.2228(4) 0.4948(3) 0.23228(16) 0.0338(7) Uani 1 1 d . . . . .
O3 O 0.5963(4) 0.4674(3) 0.06768(16) 0.0332(7) Uani 1 1 d . . . . .
O4 O 0.6505(4) 0.5837(3) 0.18187(18) 0.0340(7) Uani 1 1 d . . . . .
O5 O 0.4881(4) 0.3966(3) 0.17913(16) 0.0318(7) Uani 1 1 d . . . . .
O6 O 0.3699(3) 0.2900(2) 0.50153(15) 0.0264(6) Uani 1 1 d . . . . .
O7 O 0.1470(4) -0.0005(3) 0.26494(17) 0.0360(7) Uani 1 1 d . . . . .
O8 O 0.5422(4) -0.0659(3) 0.42664(17) 0.0357(7) Uani 1 1 d . . . . .
O9 O 0.6380(4) 0.0945(3) 0.34777(19) 0.0361(7) Uani 1 1 d . . . . .
O10 O 0.4592(4) -0.0725(3) 0.29819(17) 0.0343(7) Uani 1 1 d . . . . .
P1 P 0.53807(12) 0.49751(9) 0.13207(6) 0.0252(2) Uani 1 1 d . . . . .
P2 P 0.50462(13) -0.00316(8) 0.36752(6) 0.0261(2) Uani 1 1 d . . . . .
H3N H 0.407(7) 0.611(5) 0.023(3) 0.049(18) Uiso 1 1 d . . . . .
H6N H 0.426(7) 0.121(5) 0.480(3) 0.045(16) Uiso 1 1 d . . . . .
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'
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
C2 C1 C6 119.5(4) . . ?
C2 C1 C7 121.4(4) . . ?
C6 C1 C7 119.1(4) . . ?
C1 C2 C3 119.8(4) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 120.4(5) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.2(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.6(5) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 119.5(5) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
N1 C7 O1 112.9(3) . . ?
N1 C7 C1 129.3(4) . . ?
O1 C7 C1 117.8(4) . . ?
N2 C8 N3 128.6(4) . . ?
N2 C8 O1 113.6(3) . . ?
N3 C8 O1 117.8(4) . . ?
N3 C9 C10 115.5(3) . . ?
N3 C9 P1 107.4(3) . . ?
C10 C9 P1 110.4(3) . . ?
N3 C9 H9 107.7 . . ?
C10 C9 H9 107.7 . . ?
P1 C9 H9 107.7 . . ?
C11 C10 C15 119.7(4) . . ?
C11 C10 C9 122.4(4) . . ?
C15 C10 C9 117.9(4) . . ?
C10 C11 C12 120.9(4) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 119.3(5) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 120.7(5) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C13 119.6(4) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
O2 C15 C14 124.0(4) . . ?
O2 C15 C10 116.1(4) . . ?
C14 C15 C10 119.8(4) . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 C18 110.7(4) . . ?
O4 C17 H17A 109.5 . . ?
C18 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 O5 108.2(5) . . ?
C20 C19 H19A 110.1 . . ?
O5 C19 H19A 110.1 . . ?
C20 C19 H19B 110.1 . . ?
O5 C19 H19B 110.1 . . ?
H19A C19 H19B 108.4 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C26 119.2(4) . . ?
C22 C21 C27 121.5(4) . . ?
C26 C21 C27 119.3(4) . . ?
C23 C22 C21 121.0(4) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C24 119.4(5) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C25 C24 C23 119.9(5) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 121.1(5) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C25 C26 C21 119.3(5) . . ?
C25 C26 H26 120.3 . . ?
C21 C26 H26 120.3 . . ?
N4 C27 O6 112.7(4) . . ?
N4 C27 C21 129.3(4) . . ?
O6 C27 C21 118.0(4) . . ?
N5 C28 N6 129.1(4) . . ?
N5 C28 O6 113.8(4) . . ?
N6 C28 O6 117.1(4) . . ?
N6 C29 C30 115.7(4) . . ?
N6 C29 P2 107.7(3) . . ?
C30 C29 P2 108.5(3) . . ?
N6 C29 H29 108.2 . . ?
C30 C29 H29 108.2 . . ?
P2 C29 H29 108.2 . . ?
C31 C30 C35 119.4(4) . . ?
C31 C30 C29 121.0(4) . . ?
C35 C30 C29 119.4(4) . . ?
C30 C31 C32 120.8(5) . . ?
C30 C31 H31 119.6 . . ?
C32 C31 H31 119.6 . . ?
C33 C32 C31 118.9(5) . . ?
C33 C32 H32 120.6 . . ?
C31 C32 H32 120.6 . . ?
C32 C33 C34 122.1(5) . . ?
C32 C33 H33 118.9 . . ?
C34 C33 H33 118.9 . . ?
C33 C34 C35 118.9(5) . . ?
C33 C34 H34 120.6 . . ?
C35 C34 H34 120.6 . . ?
O7 C35 C34 124.5(5) . . ?
O7 C35 C30 115.7(4) . . ?
C34 C35 C30 119.8(5) . . ?
O7 C36 H36A 109.5 . . ?
O7 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
O7 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O9 C37 C38 108.4(4) . . ?
O9 C37 H37A 110.0 . . ?
C38 C37 H37A 110.0 . . ?
O9 C37 H37B 110.0 . . ?
C38 C37 H37B 110.0 . . ?
H37A C37 H37B 108.4 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
O10 C39 C40 109.3(4) . . ?
O10 C39 H39A 109.8 . . ?
C40 C39 H39A 109.8 . . ?
O10 C39 H39B 109.8 . . ?
C40 C39 H39B 109.8 . . ?
H39A C39 H39B 108.3 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C7 N1 N2 107.1(3) . . ?
C8 N2 N1 104.9(3) . . ?
C8 N3 C9 117.2(3) . . ?
C8 N3 H3N 112(5) . . ?
C9 N3 H3N 121(5) . . ?
C27 N4 N5 106.9(3) . . ?
C28 N5 N4 105.0(3) . . ?
C28 N6 C29 117.3(4) . . ?
C28 N6 H6N 110(4) . . ?
C29 N6 H6N 129(4) . . ?
C8 O1 C7 101.5(3) . . ?
C15 O2 C16 117.8(4) . . ?
C17 O4 P1 122.2(3) . . ?
C19 O5 P1 119.9(3) . . ?
C28 O6 C27 101.5(3) . . ?
C35 O7 C36 117.9(4) . . ?
C37 O9 P2 119.4(3) . . ?
C39 O10 P2 123.0(3) . . ?
O3 P1 O4 117.8(2) . . ?
O3 P1 O5 112.59(18) . . ?
O4 P1 O5 102.87(18) . . ?
O3 P1 C9 113.93(19) . . ?
O4 P1 C9 100.43(18) . . ?
O5 P1 C9 107.84(18) . . ?
O8 P2 O9 115.9(2) . . ?
O8 P2 O10 114.35(19) . . ?
O9 P2 O10 102.72(19) . . ?
O8 P2 C29 113.3(2) . . ?
O9 P2 C29 102.87(18) . . ?
O10 P2 C29 106.36(19) . . ?
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 1.392(6) . ?
C1 C6 1.404(6) . ?
C1 C7 1.461(6) . ?
C2 C3 1.394(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.372(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(7) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.275(6) . ?
C7 O1 1.385(5) . ?
C8 N2 1.304(5) . ?
C8 N3 1.341(5) . ?
C8 O1 1.365(5) . ?
C9 N3 1.457(5) . ?
C9 C10 1.521(6) . ?
C9 P1 1.828(4) . ?
C9 H9 1.0000 . ?
C10 C11 1.387(6) . ?
C10 C15 1.396(6) . ?
C11 C12 1.390(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.397(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.395(6) . ?
C14 H14 0.9500 . ?
C15 O2 1.364(5) . ?
C16 O2 1.420(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 O4 1.463(6) . ?
C17 C18 1.483(8) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.459(8) . ?
C19 O5 1.488(6) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.392(6) . ?
C21 C26 1.394(6) . ?
C21 C27 1.453(6) . ?
C22 C23 1.385(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.391(7) . ?
C23 H23 0.9500 . ?
C24 C25 1.371(9) . ?
C24 H24 0.9500 . ?
C25 C26 1.392(8) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 N4 1.281(6) . ?
C27 O6 1.384(5) . ?
C28 N5 1.297(5) . ?
C28 N6 1.347(5) . ?
C28 O6 1.365(5) . ?
C29 N6 1.454(5) . ?
C29 C30 1.523(6) . ?
C29 P2 1.814(4) . ?
C29 H29 1.0000 . ?
C30 C31 1.377(7) . ?
C30 C35 1.405(7) . ?
C31 C32 1.398(7) . ?
C31 H31 0.9500 . ?
C32 C33 1.371(9) . ?
C32 H32 0.9500 . ?
C33 C34 1.377(8) . ?
C33 H33 0.9500 . ?
C34 C35 1.401(7) . ?
C34 H34 0.9500 . ?
C35 O7 1.361(6) . ?
C36 O7 1.431(6) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 O9 1.458(6) . ?
C37 C38 1.473(7) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 O10 1.467(6) . ?
C39 C40 1.488(7) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
N1 N2 1.419(5) . ?
N3 H3N 0.81(6) . ?
N4 N5 1.419(5) . ?
N6 H6N 0.85(6) . ?
O3 P1 1.471(3) . ?
O4 P1 1.562(3) . ?
O5 P1 1.573(3) . ?
O8 P2 1.467(3) . ?
O9 P2 1.569(3) . ?
O10 P2 1.572(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3N O3 0.81(6) 2.01(7) 2.815(5) 173(6) 2_665
N6 H6N O8 0.85(6) 1.97(6) 2.804(5) 167(6) 2_656
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
C6 C1 C2 C3 -0.1(7) . . . . ?
C7 C1 C2 C3 -177.8(4) . . . . ?
C1 C2 C3 C4 1.0(7) . . . . ?
C2 C3 C4 C5 -1.5(7) . . . . ?
C3 C4 C5 C6 1.2(8) . . . . ?
C4 C5 C6 C1 -0.4(8) . . . . ?
C2 C1 C6 C5 -0.2(7) . . . . ?
C7 C1 C6 C5 177.5(4) . . . . ?
C2 C1 C7 N1 174.5(5) . . . . ?
C6 C1 C7 N1 -3.1(7) . . . . ?
C2 C1 C7 O1 -3.8(6) . . . . ?
C6 C1 C7 O1 178.5(4) . . . . ?
N3 C9 C10 C11 31.8(6) . . . . ?
P1 C9 C10 C11 -90.3(4) . . . . ?
N3 C9 C10 C15 -150.3(4) . . . . ?
P1 C9 C10 C15 87.6(4) . . . . ?
C15 C10 C11 C12 -1.5(7) . . . . ?
C9 C10 C11 C12 176.4(4) . . . . ?
C10 C11 C12 C13 -0.1(7) . . . . ?
C11 C12 C13 C14 0.8(8) . . . . ?
C12 C13 C14 C15 0.1(8) . . . . ?
C13 C14 C15 O2 178.2(4) . . . . ?
C13 C14 C15 C10 -1.7(7) . . . . ?
C11 C10 C15 O2 -177.5(4) . . . . ?
C9 C10 C15 O2 4.5(5) . . . . ?
C11 C10 C15 C14 2.4(6) . . . . ?
C9 C10 C15 C14 -175.6(4) . . . . ?
C26 C21 C22 C23 0.3(7) . . . . ?
C27 C21 C22 C23 -179.9(4) . . . . ?
C21 C22 C23 C24 0.2(8) . . . . ?
C22 C23 C24 C25 -1.8(9) . . . . ?
C23 C24 C25 C26 2.9(12) . . . . ?
C24 C25 C26 C21 -2.4(12) . . . . ?
C22 C21 C26 C25 0.8(9) . . . . ?
C27 C21 C26 C25 -179.0(6) . . . . ?
C22 C21 C27 N4 -177.9(5) . . . . ?
C26 C21 C27 N4 1.9(7) . . . . ?
C22 C21 C27 O6 1.4(6) . . . . ?
C26 C21 C27 O6 -178.8(4) . . . . ?
N6 C29 C30 C31 -37.4(6) . . . . ?
P2 C29 C30 C31 83.8(5) . . . . ?
N6 C29 C30 C35 146.4(4) . . . . ?
P2 C29 C30 C35 -92.4(4) . . . . ?
C35 C30 C31 C32 0.4(8) . . . . ?
C29 C30 C31 C32 -175.8(5) . . . . ?
C30 C31 C32 C33 1.4(9) . . . . ?
C31 C32 C33 C34 -1.5(10) . . . . ?
C32 C33 C34 C35 -0.1(9) . . . . ?
C33 C34 C35 O7 -178.4(5) . . . . ?
C33 C34 C35 C30 1.9(7) . . . . ?
C31 C30 C35 O7 178.3(4) . . . . ?
C29 C30 C35 O7 -5.4(6) . . . . ?
C31 C30 C35 C34 -2.0(7) . . . . ?
C29 C30 C35 C34 174.3(4) . . . . ?
O1 C7 N1 N2 -0.4(5) . . . . ?
C1 C7 N1 N2 -178.9(4) . . . . ?
N3 C8 N2 N1 176.9(4) . . . . ?
O1 C8 N2 N1 -0.6(5) . . . . ?
C7 N1 N2 C8 0.6(5) . . . . ?
N2 C8 N3 C9 6.3(7) . . . . ?
O1 C8 N3 C9 -176.2(3) . . . . ?
C10 C9 N3 C8 84.9(5) . . . . ?
P1 C9 N3 C8 -151.4(3) . . . . ?
O6 C27 N4 N5 0.1(5) . . . . ?
C21 C27 N4 N5 179.4(4) . . . . ?
N6 C28 N5 N4 -176.8(4) . . . . ?
O6 C28 N5 N4 1.0(5) . . . . ?
C27 N4 N5 C28 -0.6(5) . . . . ?
N5 C28 N6 C29 0.5(7) . . . . ?
O6 C28 N6 C29 -177.3(3) . . . . ?
C30 C29 N6 C28 -82.1(5) . . . . ?
P2 C29 N6 C28 156.3(3) . . . . ?
N2 C8 O1 C7 0.4(4) . . . . ?
N3 C8 O1 C7 -177.5(4) . . . . ?
N1 C7 O1 C8 0.1(5) . . . . ?
C1 C7 O1 C8 178.7(4) . . . . ?
C14 C15 O2 C16 4.4(6) . . . . ?
C10 C15 O2 C16 -175.7(4) . . . . ?
C18 C17 O4 P1 95.5(5) . . . . ?
C20 C19 O5 P1 169.1(4) . . . . ?
N5 C28 O6 C27 -0.9(5) . . . . ?
N6 C28 O6 C27 177.2(4) . . . . ?
N4 C27 O6 C28 0.5(5) . . . . ?
C21 C27 O6 C28 -179.0(4) . . . . ?
C34 C35 O7 C36 1.7(7) . . . . ?
C30 C35 O7 C36 -178.6(4) . . . . ?
C38 C37 O9 P2 155.4(4) . . . . ?
C40 C39 O10 P2 -97.0(5) . . . . ?
C17 O4 P1 O3 -55.0(4) . . . . ?
C17 O4 P1 O5 69.5(4) . . . . ?
C17 O4 P1 C9 -179.3(4) . . . . ?
C19 O5 P1 O3 -30.0(4) . . . . ?
C19 O5 P1 O4 -157.8(3) . . . . ?
C19 O5 P1 C9 96.6(4) . . . . ?
N3 C9 P1 O3 -38.6(3) . . . . ?
C10 C9 P1 O3 88.2(3) . . . . ?
N3 C9 P1 O4 88.4(3) . . . . ?
C10 C9 P1 O4 -144.8(3) . . . . ?
N3 C9 P1 O5 -164.3(3) . . . . ?
C10 C9 P1 O5 -37.6(3) . . . . ?
C37 O9 P2 O8 46.1(5) . . . . ?
C37 O9 P2 O10 -79.3(4) . . . . ?
C37 O9 P2 C29 170.3(4) . . . . ?
C39 O10 P2 O8 29.1(4) . . . . ?
C39 O10 P2 O9 155.5(4) . . . . ?
C39 O10 P2 C29 -96.8(4) . . . . ?
N6 C29 P2 O8 58.2(3) . . . . ?
C30 C29 P2 O8 -67.8(4) . . . . ?
N6 C29 P2 O9 -67.7(3) . . . . ?
C30 C29 P2 O9 166.3(3) . . . . ?
N6 C29 P2 O10 -175.3(3) . . . . ?
C30 C29 P2 O10 58.7(3) . . . . ?
