#------------------------------------------------------------------------------
#$Date: 2024-08-31 05:04:27 +0300 (Sat, 31 Aug 2024) $
#$Revision: 294310 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/32/2023241.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2023241
loop_
_publ_author_name
'Wackerle, Brandon G.'
'Werner, Eric J.'
'Staples, Richard J.'
'Biros, Shannon M.'
_publ_section_title
;
 Crystal structure of a tris(2-aminoethyl)methane capped
 carbamoylmethylphosphine oxide compound
;
_journal_coeditor_code           VU2007
_journal_issue                   9
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_page_first              993
_journal_page_last               996
_journal_paper_doi               10.1107/S2056989024008478
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C25 H52 N3 O12 P3'
_chemical_formula_moiety         'C25 H52 N3 O12 P3'
_chemical_formula_sum            'C25 H52 N3 O12 P3'
_chemical_formula_weight         679.60
_chemical_name_systematic
'Diethyl {[(5-[2-(diethoxyphosphoryl)acetamido]-3-{2-[2-(diethoxyphosphoryl)acetamido]ethyl}pentyl)carbamoyl]methyl}phosphonate'
_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     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_cell_angle_alpha                100.4792(11)
_cell_angle_beta                 100.1240(10)
_cell_angle_gamma                111.1313(11)
_cell_formula_units_Z            2
_cell_length_a                   10.02487(11)
_cell_length_b                   11.92992(15)
_cell_length_c                   16.6237(2)
_cell_measurement_reflns_used    13811
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.8460
_cell_measurement_theta_min      4.1040
_cell_volume                     1759.25(4)
_computing_cell_refinement
;
CrysAlisPro 1.171.42.69a (Oxford Diffraction, 2006)
;
_computing_data_collection
;
CrysAlisPro 1.171.42.69a (Oxford Diffraction, 2006)
;
_computing_data_reduction
;
CrysAlisPro 1.171.42.69a (Oxford Diffraction, 2006)
;
_computing_molecular_graphics
;
CrystalMaker (Palmer, 2007)
;
_computing_publication_material
;
Olex2 (Dolomanov et al., 2009; Bourhis et al.,
2015)
;
_computing_structure_refinement
;
SHELXL2019/2 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT  (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy-S, Dualflex, HyPix-6000HE'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27502
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.209
_diffrn_reflns_theta_min         2.802
_exptl_absorpt_coefficient_mu    2.056
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.700
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlisPro; Oxford Diffraction, 2006)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       irregular
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.163
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.036
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.345
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         7504
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0371
_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)+(0.0443P)²+0.5632P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.0993
_reflns_number_gt                6481
_reflns_number_total             7504
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vu2007.cif
_cod_data_source_block           I
_cod_database_code               2023241
_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   0.730
_shelx_estimated_absorpt_t_max   0.930
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 0.35890(4) 0.68848(4) 0.12527(2) 0.02154(10) Uani d 1 . .
P P2 0.53282(4) 0.38100(4) 0.20227(2) 0.02071(9) Uani d 1 . .
P P3 0.47290(4) 0.71266(4) 0.45959(2) 0.02314(10) Uani d 1 . .
O O1 0.62953(12) 0.82490(11) 0.04850(8) 0.0286(2) Uani d 1 . .
O O2 0.69588(13) 0.99779(11) 0.49775(7) 0.0314(3) Uani d 1 . .
O O3 0.86359(13) 0.48663(12) 0.29651(8) 0.0336(3) Uani d 1 . .
O O4 0.45143(13) 0.75898(12) 0.21164(7) 0.0310(3) Uani d 1 . .
O O5 0.58783(13) 0.66867(11) 0.44337(8) 0.0304(3) Uani d 1 . .
O O6 0.59114(12) 0.46394(10) 0.14955(7) 0.0261(2) Uani d 1 . .
O O7 0.28427(12) 0.76460(10) 0.07967(8) 0.0283(2) Uani d 1 . .
O O8 0.22248(12) 0.56567(11) 0.11756(8) 0.0276(2) Uani d 1 . .
O O9 0.48562(12) 0.75646(11) 0.55729(7) 0.0274(2) Uani d 1 . .
O O10 0.30802(13) 0.61449(11) 0.42340(8) 0.0299(3) Uani d 1 . .
O O11 0.53576(12) 0.24858(10) 0.17424(7) 0.0249(2) Uani d 1 . .
O O12 0.36511(12) 0.34604(11) 0.20133(7) 0.0267(2) Uani d 1 . .
N N1 0.71852(14) 0.70410(14) 0.11270(9) 0.0242(3) Uani d 1 . .
H H1 0.693(2) 0.636(2) 0.1277(13) 0.025(5) Uiso d 1 . .
N N2 0.66717(15) 0.94335(13) 0.35606(9) 0.0248(3) Uani d 1 . .
H H2 0.614(2) 0.896(2) 0.3124(15) 0.030(5) Uiso d 1 . .
N N3 0.82763(15) 0.64181(13) 0.37830(9) 0.0250(3) Uani d 1 . .
H H3 0.766(2) 0.661(2) 0.3961(14) 0.029(5) Uiso d 1 . .
C C1 0.89282(17) 0.85561(16) 0.29672(10) 0.0270(3) Uani d 1 . .
H H1A 0.791(2) 0.7973(18) 0.2865(13) 0.025(5) Uiso d 1 . .
C C5 0.87290(17) 0.79247(17) 0.13561(11) 0.0296(3) Uani d 1 . .
H H5AA 0.893030 0.827828 0.087376 0.036 Uiso calc 0.676(3) A 1
H H5AB 0.937439 0.747536 0.145957 0.036 Uiso calc 0.676(3) A 1
H H5BC 0.878553 0.876708 0.134409 0.036 Uiso calc 0.324(3) A 2
H H5BD 0.924175 0.767149 0.094618 0.036 Uiso calc 0.324(3) A 2
C C6 0.81521(18) 1.02970(15) 0.35924(11) 0.0282(3) Uani d 1 . .
H H6AA 0.846342 1.105489 0.406285 0.034 Uiso calc 0.676(3) A 1
H H6AB 0.812996 1.055031 0.305686 0.034 Uiso calc 0.676(3) A 1
H H6BC 0.882153 1.049504 0.416062 0.034 Uiso calc 0.324(3) A 2
H H6BD 0.811939 1.108309 0.349705 0.034 Uiso calc 0.324(3) A 2
C C7 0.97830(17) 0.73567(16) 0.39527(11) 0.0287(3) Uani d 1 . .
H H7AA 1.049062 0.696112 0.404807 0.034 Uiso calc 0.676(3) A 1
H H7AB 0.999863 0.800928 0.447785 0.034 Uiso calc 0.676(3) A 1
H H7BC 1.030570 0.707191 0.356172 0.034 Uiso calc 0.324(3) A 2
H H7BD 1.034145 0.749897 0.454197 0.034 Uiso calc 0.324(3) A 2
C C8 0.60896(16) 0.72964(15) 0.07237(9) 0.0223(3) Uani d 1 . .
C C9 0.62078(18) 0.93312(14) 0.42602(10) 0.0243(3) Uani d 1 . .
C C10 0.78257(17) 0.52657(15) 0.32878(10) 0.0249(3) Uani d 1 . .
C C11 0.45376(16) 0.63076(14) 0.05793(10) 0.0223(3) Uani d 1 . .
H H11A 0.459884 0.554470 0.070441 0.027 Uiso calc 1 . .
H H11B 0.398214 0.608946 -0.002128 0.027 Uiso calc 1 . .
C C12 0.46608(17) 0.83407(15) 0.41182(10) 0.0249(3) Uani d 1 . .
H H12A 0.419042 0.798180 0.350200 0.030 Uiso calc 1 . .
H H12B 0.404881 0.872627 0.436542 0.030 Uiso calc 1 . .
C C13 0.61943(17) 0.44487(15) 0.31384(10) 0.0258(3) Uani d 1 . .
H H13A 0.569838 0.494936 0.339364 0.031 Uiso calc 1 . .
H H13B 0.609095 0.376363 0.341386 0.031 Uiso calc 1 . .
C C14 0.36017(19) 0.89977(15) 0.09918(12) 0.0308(4) Uani d 1 . .
H H14A 0.447502 0.922709 0.075691 0.037 Uiso calc 1 . .
H H14B 0.394467 0.936564 0.161344 0.037 Uiso calc 1 . .
C C15 0.2526(2) 0.94742(19) 0.06022(16) 0.0436(5) Uani d 1 . .
H H15A 0.217905 0.909149 -0.001106 0.065 Uiso calc 1 . .
H H15B 0.301497 1.038212 0.071238 0.065 Uiso calc 1 . .
H H15C 0.167935 0.926141 0.085007 0.065 Uiso calc 1 . .
C C16 0.1174(2) 0.56953(19) 0.16770(12) 0.0359(4) Uani d 1 . .
H H16A 0.136218 0.657160 0.193669 0.043 Uiso calc 1 . .
H H16B 0.129442 0.528868 0.213731 0.043 Uiso calc 1 . .
C C17 -0.0359(2) 0.5030(2) 0.11089(15) 0.0528(6) Uani d 1 . .
H H17A -0.046762 0.543631 0.065403 0.079 Uiso calc 1 . .
H H17B -0.107391 0.505756 0.143687 0.079 Uiso calc 1 . .
H H17C -0.054202 0.416041 0.086221 0.079 Uiso calc 1 . .
C C18 0.62943(17) 0.81483(17) 0.61951(10) 0.0287(3) Uani d 1 . .
H H18A 0.708701 0.850973 0.591946 0.034 Uiso calc 1 . .
H H18B 0.650082 0.752204 0.645208 0.034 Uiso calc 1 . .
C C19 0.6248(2) 0.91549(17) 0.68647(12) 0.0343(4) Uani d 1 . .
H H19A 0.612075 0.980235 0.661174 0.051 Uiso calc 1 . .
H H19B 0.717792 0.952208 0.731421 0.051 Uiso calc 1 . .
H H19C 0.541637 0.879707 0.710529 0.051 Uiso calc 1 . .
C C20 0.2548(2) 0.5026(2) 0.45184(15) 0.0457(5) Uani d 1 . .
H H20A 0.209606 0.517026 0.498961 0.055 Uiso calc 1 . .
H H20B 0.338692 0.481182 0.472970 0.055 Uiso calc 1 . .
C C21 0.1447(3) 0.3995(2) 0.38158(18) 0.0587(7) Uani d 1 . .
H H21A 0.191132 0.382672 0.336272 0.088 Uiso calc 1 . .
H H21B 0.063215 0.422058 0.359740 0.088 Uiso calc 1 . .
H H21C 0.105937 0.324849 0.401657 0.088 Uiso calc 1 . .
C C22 0.64205(19) 0.22577(17) 0.13194(11) 0.0291(3) Uani d 1 . .
H H22A 0.708598 0.304258 0.122922 0.035 Uiso calc 1 . .
H H22B 0.589477 0.164576 0.075948 0.035 Uiso calc 1 . .
C C23 0.7309(2) 0.17610(18) 0.18627(13) 0.0364(4) Uani d 1 . .
H H23A 0.797129 0.153545 0.156173 0.055 Uiso calc 1 . .
H H23B 0.663732 0.102142 0.198646 0.055 Uiso calc 1 . .
H H23C 0.789814 0.240173 0.239481 0.055 Uiso calc 1 . .
C C24 0.25179(18) 0.28757(16) 0.12104(11) 0.0298(3) Uani d 1 . .
H H24A 0.282073 0.234942 0.081284 0.036 Uiso calc 1 . .
H H24B 0.237004 0.352005 0.095038 0.036 Uiso calc 1 . .
C C25 0.1120(2) 0.2097(3) 0.13888(17) 0.0668(8) Uani d 1 . .
H H25A 0.032790 0.170273 0.085977 0.100 Uiso calc 1 . .
H H25B 0.084140 0.262460 0.179047 0.100 Uiso calc 1 . .
H H25C 0.127335 0.145065 0.163357 0.100 Uiso calc 1 . .
C C2 0.9138(3) 0.9024(2) 0.21687(16) 0.0273(5) Uani d 0.676(3) A 1
H H2A 1.018299 0.961080 0.227461 0.033 Uiso calc 0.676(3) A 1
H H2B 0.850660 0.948454 0.206276 0.033 Uiso calc 0.676(3) A 1
C C3 0.9259(3) 0.9732(2) 0.37186(16) 0.0286(6) Uani d 0.676(3) A 1
H H3A 0.927444 0.947845 0.425396 0.034 Uiso calc 0.676(3) A 1
H H3B 1.025648 1.037297 0.377840 0.034 Uiso calc 0.676(3) A 1
C C4 1.0018(2) 0.7972(2) 0.32176(16) 0.0276(6) Uani d 0.676(3) A 1
H H4A 1.103868 0.862754 0.338242 0.033 Uiso calc 0.676(3) A 1
H H4B 0.993196 0.733465 0.271490 0.033 Uiso calc 0.676(3) A 1
C C2A 0.9477(5) 0.7944(5) 0.2254(3) 0.0269(11) Uani d 0.324(3) A 2
H H2AA 1.056167 0.840578 0.236832 0.032 Uiso calc 0.324(3) A 2
H H2AB 0.928389 0.707658 0.227536 0.032 Uiso calc 0.324(3) A 2
C C3A 0.8789(5) 0.9696(5) 0.2877(3) 0.0263(11) Uani d 0.324(3) A 2
H H3AA 0.812478 0.952468 0.231216 0.032 Uiso calc 0.324(3) A 2
H H3AB 0.977608 1.031831 0.289758 0.032 Uiso calc 0.324(3) A 2
C C4A 0.9682(6) 0.8531(5) 0.3825(3) 0.0292(12) Uani d 0.324(3) A 2
H H4AA 1.070549 0.918112 0.398768 0.035 Uiso calc 0.324(3) A 2
H H4AB 0.916861 0.878735 0.423347 0.035 Uiso calc 0.324(3) A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 0 -3 0.0756
2 -5 9 0.0319
5 -2 6 0.0375
-1 5 -9 0.0495
4 -5 -6 0.0229
-4 6 5 0.0122
-1 -1 1 0.0724
3 4 -5 0.0829
-4 5 6 0.0095
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O4 P1 O7 . . 112.90(7) ?
O4 P1 O8 . . 116.05(7) ?
O4 P1 C11 . . 114.00(7) ?
O7 P1 C11 . . 108.90(7) ?
O8 P1 O7 . . 102.52(6) ?
O8 P1 C11 . . 101.26(7) ?
O6 P2 O11 . . 113.64(6) ?
O6 P2 O12 . . 115.95(7) ?
O6 P2 C13 . . 114.70(7) ?
O11 P2 C13 . . 108.50(7) ?
O12 P2 O11 . . 101.94(6) ?
O12 P2 C13 . . 100.62(7) ?
O5 P3 O9 . . 112.76(7) ?
O5 P3 O10 . . 116.32(7) ?
O5 P3 C12 . . 114.34(7) ?
O9 P3 C12 . . 108.77(7) ?
O10 P3 O9 . . 102.72(6) ?
O10 P3 C12 . . 100.66(7) ?
C14 O7 P1 . . 119.89(10) ?
C16 O8 P1 . . 119.61(11) ?
C18 O9 P3 . . 120.98(10) ?
C20 O10 P3 . . 121.18(11) ?
C22 O11 P2 . . 123.56(10) ?
C24 O12 P2 . . 119.46(10) ?
C5 N1 H1 . . 121.2(14) ?
C8 N1 H1 . . 117.1(14) ?
C8 N1 C5 . . 121.51(15) ?
C6 N2 H2 . . 119.9(16) ?
C9 N2 H2 . . 117.7(16) ?
C9 N2 C6 . . 122.08(14) ?
C7 N3 H3 . . 119.5(15) ?
C10 N3 H3 . . 117.9(15) ?
C10 N3 C7 . . 122.40(15) ?
C2 C1 H1A . . 109.5(12) ?
C2 C1 C3 . . 107.39(17) ?
C3 C1 H1A . . 108.6(12) ?
C4 C1 H1A . . 111.6(12) ?
C4 C1 C2 . . 110.97(17) ?
C4 C1 C3 . . 108.61(16) ?
C2A C1 H1A . . 103.4(12) ?
C3A C1 H1A . . 103.2(12) ?
C3A C1 C2A . . 114.5(3) ?
C3A C1 C4A . . 118.3(3) ?
C4A C1 H1A . . 104.2(12) ?
C4A C1 C2A . . 111.1(3) ?
N1 C5 H5AA . . 109.0 ?
N1 C5 H5AB . . 109.0 ?
N1 C5 H5BC . . 110.0 ?
N1 C5 H5BD . . 110.0 ?
N1 C5 C2 . . 113.05(14) ?
N1 C5 C2A . . 108.5(2) ?
H5AA C5 H5AB . . 107.8 ?
H5BC C5 H5BD . . 108.4 ?
C2 C5 H5AA . . 109.0 ?
C2 C5 H5AB . . 109.0 ?
C2A C5 H5BC . . 110.0 ?
C2A C5 H5BD . . 110.0 ?
N2 C6 H6AA . . 109.2 ?
N2 C6 H6AB . . 109.2 ?
N2 C6 H6BC . . 109.5 ?
N2 C6 H6BD . . 109.5 ?
N2 C6 C3 . . 111.97(16) ?
N2 C6 C3A . . 110.5(2) ?
H6AA C6 H6AB . . 107.9 ?
H6BC C6 H6BD . . 108.1 ?
C3 C6 H6AA . . 109.2 ?
C3 C6 H6AB . . 109.2 ?
C3A C6 H6BC . . 109.5 ?
C3A C6 H6BD . . 109.5 ?
N3 C7 H7AA . . 109.1 ?
N3 C7 H7AB . . 109.1 ?
N3 C7 H7BC . . 110.1 ?
N3 C7 H7BD . . 110.1 ?
N3 C7 C4 . . 112.46(15) ?
N3 C7 C4A . . 107.8(2) ?
H7AA C7 H7AB . . 107.8 ?
H7BC C7 H7BD . . 108.5 ?
C4 C7 H7AA . . 109.1 ?
C4 C7 H7AB . . 109.1 ?
C4A C7 H7BC . . 110.1 ?
C4A C7 H7BD . . 110.1 ?
O1 C8 N1 . . 123.86(14) ?
O1 C8 C11 . . 121.44(14) ?
N1 C8 C11 . . 114.70(14) ?
O2 C9 N2 . . 123.68(15) ?
O2 C9 C12 . . 121.02(15) ?
N2 C9 C12 . . 115.30(14) ?
O3 C10 N3 . . 124.25(15) ?
O3 C10 C13 . . 120.97(15) ?
N3 C10 C13 . . 114.78(14) ?
P1 C11 H11A . . 109.7 ?
P1 C11 H11B . . 109.7 ?
C8 C11 P1 . . 109.70(10) ?
C8 C11 H11A . . 109.7 ?
C8 C11 H11B . . 109.7 ?
H11A C11 H11B . . 108.2 ?
P3 C12 H12A . . 109.5 ?
P3 C12 H12B . . 109.5 ?
C9 C12 P3 . . 110.80(11) ?
C9 C12 H12A . . 109.5 ?
C9 C12 H12B . . 109.5 ?
H12A C12 H12B . . 108.1 ?
P2 C13 H13A . . 109.6 ?
P2 C13 H13B . . 109.6 ?
C10 C13 P2 . . 110.07(11) ?
C10 C13 H13A . . 109.6 ?
C10 C13 H13B . . 109.6 ?
H13A C13 H13B . . 108.2 ?
O7 C14 H14A . . 110.2 ?
O7 C14 H14B . . 110.2 ?
O7 C14 C15 . . 107.68(14) ?
H14A C14 H14B . . 108.5 ?
C15 C14 H14A . . 110.2 ?
C15 C14 H14B . . 110.2 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15B . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
O8 C16 H16A . . 110.0 ?
O8 C16 H16B . . 110.0 ?
O8 C16 C17 . . 108.68(15) ?
H16A C16 H16B . . 108.3 ?
C17 C16 H16A . . 110.0 ?
C17 C16 H16B . . 110.0 ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
C16 C17 H17C . . 109.5 ?
H17A C17 H17B . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
O9 C18 H18A . . 110.2 ?
O9 C18 H18B . . 110.2 ?
O9 C18 C19 . . 107.77(14) ?
H18A C18 H18B . . 108.5 ?
C19 C18 H18A . . 110.2 ?
C19 C18 H18B . . 110.2 ?
C18 C19 H19A . . 109.5 ?
C18 C19 H19B . . 109.5 ?
C18 C19 H19C . . 109.5 ?
H19A C19 H19B . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
O10 C20 H20A . . 109.7 ?
O10 C20 H20B . . 109.7 ?
O10 C20 C21 . . 109.73(18) ?
H20A C20 H20B . . 108.2 ?
C21 C20 H20A . . 109.7 ?
C21 C20 H20B . . 109.7 ?
C20 C21 H21A . . 109.5 ?
C20 C21 H21B . . 109.5 ?
C20 C21 H21C . . 109.5 ?
H21A C21 H21B . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
O11 C22 H22A . . 109.9 ?
O11 C22 H22B . . 109.9 ?
O11 C22 C23 . . 108.74(14) ?
H22A C22 H22B . . 108.3 ?
C23 C22 H22A . . 109.9 ?
C23 C22 H22B . . 109.9 ?
C22 C23 H23A . . 109.5 ?
C22 C23 H23B . . 109.5 ?
C22 C23 H23C . . 109.5 ?
H23A C23 H23B . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
O12 C24 H24A . . 110.2 ?
O12 C24 H24B . . 110.2 ?
O12 C24 C25 . . 107.54(16) ?
H24A C24 H24B . . 108.5 ?
C25 C24 H24A . . 110.2 ?
C25 C24 H24B . . 110.2 ?
C24 C25 H25A . . 109.5 ?
C24 C25 H25B . . 109.5 ?
C24 C25 H25C . . 109.5 ?
H25A C25 H25B . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
C1 C2 C5 . . 112.41(18) ?
C1 C2 H2A . . 109.1 ?
C1 C2 H2B . . 109.1 ?
C5 C2 H2A . . 109.1 ?
C5 C2 H2B . . 109.1 ?
H2A C2 H2B . . 107.9 ?
C1 C3 H3A . . 108.8 ?
C1 C3 H3B . . 108.8 ?
C6 C3 C1 . . 113.63(17) ?
C6 C3 H3A . . 108.8 ?
C6 C3 H3B . . 108.8 ?
H3A C3 H3B . . 107.7 ?
C1 C4 C7 . . 114.59(17) ?
C1 C4 H4A . . 108.6 ?
C1 C4 H4B . . 108.6 ?
C7 C4 H4A . . 108.6 ?
C7 C4 H4B . . 108.6 ?
H4A C4 H4B . . 107.6 ?
C1 C2A H2AA . . 108.8 ?
C1 C2A H2AB . . 108.8 ?
C5 C2A C1 . . 113.6(3) ?
C5 C2A H2AA . . 108.8 ?
C5 C2A H2AB . . 108.8 ?
H2AA C2A H2AB . . 107.7 ?
C1 C3A C6 . . 114.5(3) ?
C1 C3A H3AA . . 108.6 ?
C1 C3A H3AB . . 108.6 ?
C6 C3A H3AA . . 108.6 ?
C6 C3A H3AB . . 108.6 ?
H3AA C3A H3AB . . 107.6 ?
C1 C4A H4AA . . 107.4 ?
C1 C4A H4AB . . 107.4 ?
C7 C4A C1 . . 119.9(3) ?
C7 C4A H4AA . . 107.4 ?
C7 C4A H4AB . . 107.4 ?
H4AA C4A H4AB . . 106.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O4 . 1.4696(12) ?
P1 O7 . 1.5811(12) ?
P1 O8 . 1.5681(11) ?
P1 C11 . 1.7881(16) ?
P2 O6 . 1.4722(12) ?
P2 O11 . 1.5761(12) ?
P2 O12 . 1.5759(11) ?
P2 C13 . 1.7936(16) ?
P3 O5 . 1.4729(12) ?
P3 O9 . 1.5803(12) ?
P3 O10 . 1.5697(12) ?
P3 C12 . 1.7899(17) ?
O1 C8 . 1.231(2) ?
O2 C9 . 1.231(2) ?
O3 C10 . 1.230(2) ?
O7 C14 . 1.457(2) ?
O8 C16 . 1.4612(19) ?
O9 C18 . 1.4571(18) ?
O10 C20 . 1.448(2) ?
O11 C22 . 1.4515(19) ?
O12 C24 . 1.455(2) ?
N1 H1 . 0.86(2) ?
N1 C5 . 1.457(2) ?
N1 C8 . 1.344(2) ?
N2 H2 . 0.79(2) ?
N2 C6 . 1.455(2) ?
N2 C9 . 1.336(2) ?
N3 H3 . 0.82(2) ?
N3 C7 . 1.460(2) ?
N3 C10 . 1.335(2) ?
C1 H1A . 0.97(2) ?
C1 C2 . 1.550(3) ?
C1 C3 . 1.587(3) ?
C1 C4 . 1.532(3) ?
C1 C2A . 1.564(5) ?
C1 C3A . 1.447(5) ?
C1 C4A . 1.503(5) ?
C5 H5AA . 0.9900 ?
C5 H5AB . 0.9900 ?
C5 H5BC . 0.9900 ?
C5 H5BD . 0.9900 ?
C5 C2 . 1.577(3) ?
C5 C2A . 1.540(5) ?
C6 H6AA . 0.9900 ?
C6 H6AB . 0.9900 ?
C6 H6BC . 0.9900 ?
C6 H6BD . 0.9900 ?
C6 C3 . 1.497(3) ?
C6 C3A . 1.619(5) ?
C7 H7AA . 0.9900 ?
C7 H7AB . 0.9900 ?
C7 H7BC . 0.9900 ?
C7 H7BD . 0.9900 ?
C7 C4 . 1.546(3) ?
C7 C4A . 1.490(6) ?
C8 C11 . 1.521(2) ?
C9 C12 . 1.519(2) ?
C10 C13 . 1.519(2) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C14 C15 . 1.495(3) ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C16 C17 . 1.490(3) ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
C18 H18A . 0.9900 ?
C18 H18B . 0.9900 ?
C18 C19 . 1.502(3) ?
C19 H19A . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19C . 0.9800 ?
C20 H20A . 0.9900 ?
C20 H20B . 0.9900 ?
C20 C21 . 1.463(3) ?
C21 H21A . 0.9800 ?
C21 H21B . 0.9800 ?
C21 H21C . 0.9800 ?
C22 H22A . 0.9900 ?
C22 H22B . 0.9900 ?
C22 C23 . 1.501(2) ?
C23 H23A . 0.9800 ?
C23 H23B . 0.9800 ?
C23 H23C . 0.9800 ?
C24 H24A . 0.9900 ?
C24 H24B . 0.9900 ?
C24 C25 . 1.491(3) ?
C25 H25A . 0.9800 ?
C25 H25B . 0.9800 ?
C25 H25C . 0.9800 ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C2A H2AA . 0.9900 ?
C2A H2AB . 0.9900 ?
C3A H3AA . 0.9900 ?
C3A H3AB . 0.9900 ?
C4A H4AA . 0.9900 ?
C4A H4AB . 0.9900 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O6 . 0.86(2) 2.07(2) 2.9138(18) 168.8(19) yes
N2 H2 O4 . 0.79(2) 2.06(2) 2.8465(18) 170(2) yes
N3 H3 O5 . 0.82(2) 2.10(2) 2.8975(19) 167(2) yes
C11 H11A O6 . 0.99 2.36 3.2433(19) 148.4 yes
C11 H11B O6 2_665 0.99 2.48 3.3235(19) 142.7 yes
C12 H12A O4 . 0.99 2.37 3.2476(19) 147.5 yes
C12 H12B O2 2_676 0.99 2.35 3.321(2) 168.1 yes
C13 H13A O5 . 0.99 2.37 3.259(2) 148.5 yes
C14 H14A O1 . 0.99 2.56 3.326(2) 134.6 yes
C17 H17B O3 1_455 0.98 2.65 3.427(3) 136.6 yes
C18 H18A O2 . 0.99 2.57 3.215(2) 122.4 yes
C22 H22B O1 2_665 0.99 2.80 3.472(2) 126.2 yes
C23 H23C O3 . 0.98 2.69 3.460(2) 135.2 yes
C24 H24A O1 2_665 0.99 2.55 3.480(2) 155.9 yes
C24 H24B O8 . 0.99 2.57 3.444(2) 147.4 yes
C4A H4AA O2 2_776 0.99 2.39 3.241(5) 143.7 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
P1 O7 C14 C15 . . . . -169.31(13) ?
P1 O8 C16 C17 . . . . 131.70(16) ?
P2 O11 C22 C23 . . . . 119.26(14) ?
P2 O12 C24 C25 . . . . 151.86(17) ?
P3 O9 C18 C19 . . . . 142.53(12) ?
P3 O10 C20 C21 . . . . -145.69(17) ?
O1 C8 C11 P1 . . . . -70.88(17) ?
O2 C9 C12 P3 . . . . -65.17(18) ?
O3 C10 C13 P2 . . . . -53.21(19) ?
O4 P1 O7 C14 . . . . 31.54(14) ?
O4 P1 O8 C16 . . . . 52.59(15) ?
O4 P1 C11 C8 . . . . -41.31(13) ?
O5 P3 O9 C18 . . . . 33.23(14) ?
O5 P3 O10 C20 . . . . 62.32(17) ?
O5 P3 C12 C9 . . . . -45.33(13) ?
O6 P2 O11 C22 . . . . 27.99(14) ?
O6 P2 O12 C24 . . . . 56.73(14) ?
O6 P2 C13 C10 . . . . -34.53(14) ?
O7 P1 O8 C16 . . . . -70.93(14) ?
O7 P1 C11 C8 . . . . 85.75(12) ?
O8 P1 O7 C14 . . . . 157.15(12) ?
O8 P1 C11 C8 . . . . -166.67(11) ?
O9 P3 O10 C20 . . . . -61.33(16) ?
O9 P3 C12 C9 . . . . 81.70(12) ?
O10 P3 O9 C18 . . . . 159.22(12) ?
O10 P3 C12 C9 . . . . -170.81(11) ?
O11 P2 O12 C24 . . . . -67.24(13) ?
O11 P2 C13 C10 . . . . 93.74(12) ?
O12 P2 O11 C22 . . . . 153.50(12) ?
O12 P2 C13 C10 . . . . -159.72(12) ?
N1 C5 C2 C1 . . . . 61.5(2) ?
N1 C5 C2A C1 . . . . -69.9(3) ?
N1 C8 C11 P1 . . . . 108.97(13) ?
N2 C6 C3 C1 . . . . 62.7(2) ?
N2 C6 C3A C1 . . . . -60.9(4) ?
N2 C9 C12 P3 . . . . 114.58(14) ?
N3 C7 C4 C1 . . . . 55.4(2) ?
N3 C7 C4A C1 . . . . -62.0(4) ?
N3 C10 C13 P2 . . . . 126.59(13) ?
C5 N1 C8 O1 . . . . 3.3(2) ?
C5 N1 C8 C11 . . . . -176.51(13) ?
C6 N2 C9 O2 . . . . 2.7(3) ?
C6 N2 C9 C12 . . . . -177.08(14) ?
C7 N3 C10 O3 . . . . 3.7(3) ?
C7 N3 C10 C13 . . . . -176.07(14) ?
C8 N1 C5 C2 . . . . 78.0(2) ?
C8 N1 C5 C2A . . . . 138.4(2) ?
C9 N2 C6 C3 . . . . 87.1(2) ?
C9 N2 C6 C3A . . . . 143.7(2) ?
C10 N3 C7 C4 . . . . 79.6(2) ?
C10 N3 C7 C4A . . . . 132.3(3) ?
C11 P1 O7 C14 . . . . -96.14(13) ?
C11 P1 O8 C16 . . . . 176.58(13) ?
C12 P3 O9 C18 . . . . -94.69(13) ?
C12 P3 O10 C20 . . . . -173.55(16) ?
C13 P2 O11 C22 . . . . -100.87(13) ?
C13 P2 O12 C24 . . . . -178.94(12) ?
C2 C1 C3 C6 . . . . 66.6(2) ?
C2 C1 C4 C7 . . . . -174.01(17) ?
C3 C1 C2 C5 . . . . -175.92(16) ?
C3 C1 C4 C7 . . . . 68.2(2) ?
C4 C1 C2 C5 . . . . 65.5(2) ?
C4 C1 C3 C6 . . . . -173.29(18) ?
C2A C1 C3A C6 . . . . 177.4(3) ?
C2A C1 C4A C7 . . . . -47.4(5) ?
C3A C1 C2A C5 . . . . -43.5(4) ?
C3A C1 C4A C7 . . . . 177.1(3) ?
C4A C1 C2A C5 . . . . 179.2(3) ?
C4A C1 C3A C6 . . . . -48.6(5) ?
