#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/17/2211704.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_2211704
loop_
_publ_author_name
'Xiao-Bao Chen'
'De-Qing Shi'
_publ_section_title
;O,O-Diethyl
 ({1-[(6-chloropyridin-3-yl)methyl]-5-methyl-1H-1,2,3-triazol-4-ylcarbonyloxy}phenylmethyl)phosphonate
;
_journal_coeditor_code           AT2178
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o172
_journal_page_last               o174
_journal_paper_doi               10.1107/S1600536806052391
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C21 H24 Cl N4 O5 P'
_chemical_formula_moiety         'C21 H24 Cl N4 O5 P'
_chemical_formula_sum            'C21 H24 Cl N4 O5 P'
_chemical_formula_weight         478.86
_chemical_name_systematic
;
O,O-Diethyl
({1-[(6-chloropyridin-3-yl)methyl]-5-methyl-1H-1,2,3-triazol-4-
ylcarbonyloxy}(phenyl)methyl)phosphonate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                95.865(2)
_cell_angle_beta                 92.955(2)
_cell_angle_gamma                90.536(2)
_cell_formula_units_Z            2
_cell_length_a                   8.5297(8)
_cell_length_b                   9.6214(9)
_cell_length_c                   14.6389(14)
_cell_measurement_reflns_used    5700
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.95
_cell_measurement_theta_min      2.39
_cell_volume                     1193.4(2)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10004
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.13
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  0.9739
_exptl_absorpt_correction_T_min  0.9587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick,  2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.261
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         5121
_refine_ls_number_restraints     56
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0656
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0829P)²+0.4732P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1720
_refine_ls_wR_factor_ref         0.1804
_reflns_number_gt                4282
_reflns_number_total             5121
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2178.cif
_cod_data_source_block           I
_cod_original_cell_volume        1193.37(19)
_cod_database_code               2211704
_cod_database_fobs_code          2211704
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 -0.2397(3) 1.0448(3) -0.07319(19) 0.0609(6) Uani d . 1 . .
C C2 -0.1797(3) 1.0665(3) 0.0161(2) 0.0679(7) Uani d . 1 . .
H H2 -0.1104 1.1401 0.0354 0.081 Uiso calc R 1 . .
C C3 -0.2265(3) 0.9750(3) 0.07540(19) 0.0663(7) Uani d . 1 . .
H H3 -0.1887 0.9856 0.1365 0.080 Uiso calc R 1 . .
C C4 -0.3296(3) 0.8671(3) 0.04459(17) 0.0549(6) Uani d . 1 . .
C C5 -0.3809(3) 0.8569(3) -0.04634(18) 0.0613(6) Uani d . 1 . .
H H5 -0.4502 0.7843 -0.0678 0.074 Uiso calc R 1 . .
C C6 -0.3857(3) 0.7661(3) 0.1084(2) 0.0684(7) Uani d . 1 . .
H H6A -0.4407 0.8170 0.1573 0.082 Uiso calc R 1 . .
H H6B -0.4594 0.6998 0.0746 0.082 Uiso calc R 1 . .
C C7 -0.2437(4) 0.4875(3) 0.02870(19) 0.0733(8) Uani d . 1 . .
H H7A -0.3345 0.4324 0.0387 0.110 Uiso calc R 1 . .
H H7B -0.1612 0.4270 0.0078 0.110 Uiso calc R 1 . .
H H7C -0.2701 0.5495 -0.0169 0.110 Uiso calc R 1 . .
C C8 -0.1905(3) 0.5700(3) 0.11571(16) 0.0528(5) Uani d . 1 . .
C C9 -0.0744(3) 0.5506(2) 0.18186(15) 0.0511(5) Uani d . 1 . .
C C10 0.0324(3) 0.4328(3) 0.18428(16) 0.0532(5) Uani d . 1 . .
C C11 0.2430(3) 0.3403(3) 0.27176(17) 0.0572(6) Uani d . 1 . .
H H11 0.2282 0.2659 0.2210 0.069 Uiso calc R 1 . .
C C12 0.2040(3) 0.2832(3) 0.35952(18) 0.0595(6) Uani d . 1 . .
C C13 0.2131(4) 0.1424(3) 0.3675(2) 0.0800(8) Uani d . 1 . .
H H13 0.2440 0.0818 0.3183 0.096 Uiso calc R 1 . .
C C14 0.1762(5) 0.0905(4) 0.4491(3) 0.1021(12) Uani d . 1 . .
H H14 0.1819 -0.0050 0.4538 0.123 Uiso calc R 1 . .
C C15 0.1319(5) 0.1775(5) 0.5220(3) 0.1014(12) Uani d . 1 . .
H H15 0.1092 0.1419 0.5766 0.122 Uiso calc R 1 . .
C C16 0.1211(5) 0.3152(4) 0.5150(2) 0.0958(11) Uani d . 1 . .
H H16 0.0893 0.3746 0.5645 0.115 Uiso calc R 1 . .
C C17 0.1571(4) 0.3691(3) 0.4343(2) 0.0787(8) Uani d . 1 . .
H H17 0.1497 0.4647 0.4304 0.094 Uiso calc R 1 . .
C C18 0.6920(9) 0.2576(10) 0.2838(6) 0.117(3) Uani d PDU 0.61 A 1
H H18A 0.7611 0.3388 0.2950 0.140 Uiso calc PR 0.61 A 1
H H18B 0.6950 0.2224 0.2194 0.140 Uiso calc PR 0.61 A 1
C C19 0.747(3) 0.1475(19) 0.3425(13) 0.202(9) Uani d PDU 0.61 A 1
H H19A 0.8104 0.1899 0.3941 0.302 Uiso calc PR 0.61 A 1
H H19B 0.8075 0.0803 0.3070 0.302 Uiso calc PR 0.61 A 1
H H19C 0.6575 0.1016 0.3641 0.302 Uiso calc PR 0.61 A 1
C C20 0.4521(10) 0.6727(5) 0.3424(4) 0.135(2) Uani d PDU 0.83 A 1
H H20A 0.3722 0.6915 0.2958 0.162 Uiso calc PR 0.83 A 1
H H20B 0.5530 0.7026 0.3230 0.162 Uiso calc PR 0.83 A 1
C C21 0.4190(13) 0.7485(9) 0.4290(6) 0.189(4) Uani d PDU 0.83 A 1
H H21A 0.3094 0.7388 0.4395 0.284 Uiso calc PR 0.83 A 1
H H21B 0.4452 0.8455 0.4278 0.284 Uiso calc PR 0.83 A 1
H H21C 0.4804 0.7116 0.4776 0.284 Uiso calc PR 0.83 A 1
C C18' 0.7008(11) 0.3057(13) 0.3336(11) 0.121(4) Uani d PDU 0.39 A 2
H H18C 0.7134 0.3492 0.3963 0.145 Uiso calc PR 0.39 A 2
H H18D 0.7585 0.3607 0.2942 0.145 Uiso calc PR 0.39 A 2
C C19' 0.7584(17) 0.1583(16) 0.3272(12) 0.102(5) Uani d PDU 0.39 A 2
H H19D 0.7627 0.1260 0.3872 0.153 Uiso calc PR 0.39 A 2
H H19E 0.8613 0.1551 0.3035 0.153 Uiso calc PR 0.39 A 2
H H19F 0.6879 0.0993 0.2868 0.153 Uiso calc PR 0.39 A 2
C C20' 0.532(2) 0.6496(14) 0.3961(14) 0.086(5) Uani d PDU 0.17 A 2
H H20C 0.6397 0.6439 0.3784 0.103 Uiso calc PR 0.17 A 2
H H20D 0.5343 0.6403 0.4615 0.103 Uiso calc PR 0.17 A 2
C C21' 0.481(3) 0.7964(18) 0.3853(17) 0.092(6) Uani d PDU 0.17 A 2
H H21D 0.5298 0.8290 0.3336 0.138 Uiso calc PR 0.17 A 2
H H21E 0.5125 0.8560 0.4400 0.138 Uiso calc PR 0.17 A 2
H H21F 0.3692 0.7981 0.3754 0.138 Uiso calc PR 0.17 A 2
Cl Cl1 -0.18147(11) 1.15781(9) -0.15115(6) 0.0933(3) Uani d . 1 . .
N N1 -0.3375(3) 0.9446(2) -0.10605(15) 0.0654(6) Uani d . 1 . .
N N2 -0.2561(2) 0.6899(2) 0.14852(14) 0.0587(5) Uani d . 1 . .
N N3 -0.1862(3) 0.7425(3) 0.23022(15) 0.0689(6) Uani d . 1 . .
N N4 -0.0753(3) 0.6577(2) 0.25051(14) 0.0623(5) Uani d . 1 . .
O O1 0.0269(3) 0.3309(2) 0.13015(15) 0.0853(7) Uani d . 1 . .
O O2 0.1379(2) 0.45371(19) 0.25476(12) 0.0632(5) Uani d . 1 . .
O O3 0.5391(3) 0.2953(3) 0.3040(2) 0.1131(9) Uani d D 1 . .
O O4 0.4541(3) 0.5282(3) 0.35227(17) 0.0998(8) Uani d D 1 . .
O O5 0.4726(3) 0.4590(3) 0.18017(16) 0.0932(7) Uani d . 1 . .
P P1 0.43883(9) 0.41547(9) 0.26923(5) 0.0690(2) Uani d . 1 A .
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'
Cl Cl 0.1484 0.1585 '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_publ_flag
N1 C1 C2 125.5(3) ?
N1 C1 Cl1 116.0(2) ?
C2 C1 Cl1 118.5(2) ?
C3 C2 C1 117.0(3) ?
C3 C2 H2 121.5 ?
C1 C2 H2 121.5 ?
C2 C3 C4 120.0(3) ?
C2 C3 H3 120.0 ?
C4 C3 H3 120.0 ?
C5 C4 C3 117.2(2) ?
C5 C4 C6 121.4(2) ?
C3 C4 C6 121.4(2) ?
N1 C5 C4 124.2(2) ?
N1 C5 H5 117.9 ?
C4 C5 H5 117.9 ?
N2 C6 C4 112.1(2) ?
N2 C6 H6A 109.2 ?
C4 C6 H6A 109.2 ?
N2 C6 H6B 109.2 ?
C4 C6 H6B 109.2 ?
H6A C6 H6B 107.9 ?
C8 C7 H7A 109.5 ?
C8 C7 H7B 109.5 ?
H7A C7 H7B 109.5 ?
C8 C7 H7C 109.5 ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
N2 C8 C9 103.1(2) ?
N2 C8 C7 124.0(2) ?
C9 C8 C7 132.9(2) ?
N4 C9 C8 109.6(2) ?
N4 C9 C10 122.9(2) ?
C8 C9 C10 127.5(2) ?
O1 C10 O2 124.0(2) ?
O1 C10 C9 124.8(2) ?
O2 C10 C9 111.2(2) ?
O2 C11 C12 109.4(2) ?
O2 C11 P1 104.65(17) ?
C12 C11 P1 116.11(17) ?
O2 C11 H11 108.8 ?
C12 C11 H11 108.8 ?
P1 C11 H11 108.8 ?
C13 C12 C17 117.9(3) ?
C13 C12 C11 120.5(2) ?
C17 C12 C11 121.6(2) ?
C12 C13 C14 120.1(3) ?
C12 C13 H13 120.0 ?
C14 C13 H13 120.0 ?
C15 C14 C13 120.8(3) ?
C15 C14 H14 119.6 ?
C13 C14 H14 119.6 ?
C16 C15 C14 119.8(3) ?
C16 C15 H15 120.1 ?
C14 C15 H15 120.1 ?
C15 C16 C17 120.3(3) ?
C15 C16 H16 119.8 ?
C17 C16 H16 119.8 ?
C12 C17 C16 121.1(3) ?
C12 C17 H17 119.5 ?
C16 C17 H17 119.5 ?
O3 C18 C19 109.7(10) ?
O3 C18 H18A 109.7 ?
C19 C18 H18A 109.7 ?
O3 C18 H18B 109.7 ?
C19 C18 H18B 109.7 ?
H18A C18 H18B 108.2 ?
O4 C20 C21 109.2(6) ?
O4 C20 H20A 109.8 ?
C21 C20 H20A 109.8 ?
O4 C20 H20B 109.8 ?
C21 C20 H20B 109.8 ?
H20A C20 H20B 108.3 ?
O3 C18' C19' 105.5(8) ?
O3 C18' H18C 110.6 ?
C19' C18' H18C 110.6 ?
O3 C18' H18D 110.6 ?
C19' C18' H18D 110.6 ?
H18C C18' H18D 108.8 ?
C18' C19' H19D 109.5 ?
C18' C19' H19E 109.5 ?
H19D C19' H19E 109.5 ?
C18' C19' H19F 109.5 ?
H19D C19' H19F 109.5 ?
H19E C19' H19F 109.5 ?
O4 C20' C21' 124.5(15) ?
O4 C20' H20C 106.2 ?
C21' C20' H20C 106.2 ?
O4 C20' H20D 106.2 ?
C21' C20' H20D 106.2 ?
H20C C20' H20D 106.4 ?
C20' C21' H21D 109.5 ?
C20' C21' H21E 109.5 ?
H21D C21' H21E 109.5 ?
C20' C21' H21F 109.5 ?
H21D C21' H21F 109.5 ?
H21E C21' H21F 109.5 ?
C1 N1 C5 116.0(2) ?
C8 N2 N3 111.7(2) ?
C8 N2 C6 129.2(2) ?
N3 N2 C6 119.0(2) ?
N4 N3 N2 107.3(2) ?
N3 N4 C9 108.3(2) ?
C10 O2 C11 117.80(19) ?
C18 O3 C18' 33.9(6) ?
C18 O3 P1 128.9(4) ?
C18' O3 P1 125.6(6) ?
C20 O4 C20' 43.8(8) ?
C20 O4 P1 122.6(3) ?
C20' O4 P1 148.5(9) ?
O5 P1 O4 116.88(15) yes
O5 P1 O3 117.06(16) yes
O4 P1 O3 102.06(17) yes
O5 P1 C11 113.10(13) yes
O4 P1 C11 105.50(13) yes
O3 P1 C11 100.20(13) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 1.306(3) ?
C1 C2 1.374(4) ?
C1 Cl1 1.742(3) ?
C2 C3 1.369(4) ?
C2 H2 0.9300 ?
C3 C4 1.379(4) ?
C3 H3 0.9300 ?
C4 C5 1.373(4) ?
C4 C6 1.506(4) ?
C5 N1 1.338(3) ?
C5 H5 0.9300 ?
C6 N2 1.463(3) ?
C6 H6A 0.9700 ?
C6 H6B 0.9700 ?
C7 C8 1.479(4) ?
C7 H7A 0.9600 ?
C7 H7B 0.9600 ?
C7 H7C 0.9600 ?
C8 N2 1.342(3) yes
C8 C9 1.377(3) ?
C9 N4 1.364(3) yes
C9 C10 1.463(3) ?
C10 O1 1.195(3) ?
C10 O2 1.331(3) ?
C11 O2 1.452(3) ?
C11 C12 1.499(4) ?
C11 P1 1.817(3) ?
C11 H11 0.9800 ?
C12 C13 1.374(4) ?
C12 C17 1.381(4) ?
C13 C14 1.390(5) ?
C13 H13 0.9300 ?
C14 C15 1.360(6) ?
C14 H14 0.9300 ?
C15 C16 1.342(5) ?
C15 H15 0.9300 ?
C16 C17 1.385(4) ?
C16 H16 0.9300 ?
C17 H17 0.9300 ?
C18 O3 1.395(6) ?
C18 C19 1.494(8) ?
C18 H18A 0.9700 ?
C18 H18B 0.9700 ?
C19 H19A 0.9600 ?
C19 H19B 0.9600 ?
C19 H19C 0.9600 ?
C20 O4 1.413(5) ?
C20 C21 1.439(6) ?
C20 H20A 0.9700 ?
C20 H20B 0.9700 ?
C21 H21A 0.9600 ?
C21 H21B 0.9600 ?
C21 H21C 0.9600 ?
C18' O3 1.424(8) ?
C18' C19' 1.501(9) ?
C18' H18C 0.9700 ?
C18' H18D 0.9700 ?
C19' H19D 0.9600 ?
C19' H19E 0.9600 ?
C19' H19F 0.9600 ?
C20' O4 1.415(9) ?
C20' C21' 1.502(9) ?
C20' H20C 0.9700 ?
C20' H20D 0.9700 ?
C21' H21D 0.9600 ?
C21' H21E 0.9600 ?
C21' H21F 0.9600 ?
N2 N3 1.356(3) ?
N3 N4 1.297(3) ?
O3 P1 1.556(3) ?
O4 P1 1.544(3) ?
O5 P1 1.451(2) ?
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
C7 H7B O1 . 0.96 2.59 3.158(3) 118.2
C2 H2 O1 1_565 0.93 2.44 3.333(3) 161.9
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
N1 C1 C2 C3 0.1(4)
Cl1 C1 C2 C3 -179.3(2)
C1 C2 C3 C4 -0.1(4)
C2 C3 C4 C5 0.1(4)
C2 C3 C4 C6 -178.9(2)
C3 C4 C5 N1 -0.2(4)
C6 C4 C5 N1 178.9(2)
C5 C4 C6 N2 120.5(3)
C3 C4 C6 N2 -60.5(3)
N2 C8 C9 N4 0.1(2)
C7 C8 C9 N4 -178.9(3)
N2 C8 C9 C10 177.5(2)
C7 C8 C9 C10 -1.4(4)
N4 C9 C10 O1 172.5(3)
C8 C9 C10 O1 -4.6(4)
N4 C9 C10 O2 -7.8(3)
C8 C9 C10 O2 175.1(2)
O2 C11 C12 C13 143.0(3)
P1 C11 C12 C13 -98.9(3)
O2 C11 C12 C17 -36.7(3)
P1 C11 C12 C17 81.4(3)
C17 C12 C13 C14 -0.2(5)
C11 C12 C13 C14 -179.8(3)
C12 C13 C14 C15 -0.5(6)
C13 C14 C15 C16 1.1(7)
C14 C15 C16 C17 -1.0(7)
C13 C12 C17 C16 0.3(5)
C11 C12 C17 C16 179.9(3)
C15 C16 C17 C12 0.3(6)
C2 C1 N1 C5 -0.1(4)
Cl1 C1 N1 C5 179.32(19)
C4 C5 N1 C1 0.2(4)
C9 C8 N2 N3 -0.1(3)
C7 C8 N2 N3 178.9(2)
C9 C8 N2 C6 179.4(2)
C7 C8 N2 C6 -1.5(4)
C4 C6 N2 C8 -87.9(3)
C4 C6 N2 N3 91.6(3)
C8 N2 N3 N4 0.1(3)
C6 N2 N3 N4 -179.4(2)
N2 N3 N4 C9 -0.1(3)
C8 C9 N4 N3 0.0(3)
C10 C9 N4 N3 -177.6(2)
O1 C10 O2 C11 -6.0(4)
C9 C10 O2 C11 174.24(19)
C12 C11 O2 C10 -111.1(2)
P1 C11 O2 C10 123.82(19)
C19 C18 O3 C18' 74.7(17)
C19 C18 O3 P1 172.7(10)
C19' C18' O3 C18 -51.3(14)
C19' C18' O3 P1 -160.0(9)
C21 C20 O4 C20' -55.2(13)
C21 C20 O4 P1 162.1(6)
C21' C20' O4 C20 14.4(13)
C21' C20' O4 P1 92(2)
C20 O4 P1 O5 19.4(5)
C20' O4 P1 O5 -34.0(17)
C20 O4 P1 O3 148.4(5)
C20' O4 P1 O3 95.0(17)
C20 O4 P1 C11 -107.3(5)
C20' O4 P1 C11 -160.7(17)
C18 O3 P1 O5 27.8(7)
C18' O3 P1 O5 70.6(9)
C18 O3 P1 O4 -101.1(7)
C18' O3 P1 O4 -58.3(9)
C18 O3 P1 C11 150.5(6)
C18' O3 P1 C11 -166.7(9)
O2 C11 P1 O5 -63.6(2)
C12 C11 P1 O5 175.65(19)
O2 C11 P1 O4 65.29(19)
C12 C11 P1 O4 -55.4(2)
O2 C11 P1 O3 170.96(17)
C12 C11 P1 O3 50.3(2)
