#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/65/2226583.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_2226583
loop_
_publ_author_name
'Sabbaghi, Fahimeh'
'Rostami Chaijan, Mahnaz'
'Pourayoubi, Mehrdad'
_publ_section_title
;
 N,N'-Dicyclohexyl-N,N'-dimethyl-N''-(4-nitrobenzoyl)phosphoric
 triamide
;
_journal_coeditor_code           LH5061
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1754
_journal_paper_doi               10.1107/S1600536810023524
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H33 N4 O4 P'
_chemical_formula_moiety         'C21 H33 N4 O4 P'
_chemical_formula_sum            'C21 H33 N4 O4 P'
_chemical_formula_weight         436.48
_chemical_name_systematic
;
N,N'-Dicyclohexyl-N,N'-dimethyl-N''-(4-\
nitrobenzoyl)phosphoric triamide
;
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.089(4)
_cell_angle_beta                 106.792(4)
_cell_angle_gamma                95.105(3)
_cell_formula_units_Z            2
_cell_length_a                   8.6118(16)
_cell_length_b                   10.838(2)
_cell_length_c                   12.711(2)
_cell_measurement_reflns_used    2045
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_cell_volume                     1127.3(3)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12417
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  0.9694
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.428
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         5955
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0498
_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)+(0.0010P)²+1.3000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.1033
_reflns_number_gt                4603
_reflns_number_total             5955
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5061.cif
_cod_data_source_block           I
_cod_original_cell_volume        1127.4(4)
_cod_database_code               2226583
_cod_database_fobs_code          2226583
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
P P1 0.45851(5) 0.82031(4) 0.58020(3) 0.02026(10) Uani d . 1 . .
O O1 0.48700(15) 0.85007(11) 0.47427(9) 0.0235(3) Uani d . 1 . .
O O2 0.37428(15) 0.88786(11) 0.78908(10) 0.0269(3) Uani d . 1 . .
O O3 0.60736(19) 1.44437(13) 1.10559(11) 0.0390(3) Uani d . 1 . .
O O4 0.7761(2) 1.49349(14) 1.01319(12) 0.0453(4) Uani d . 1 . .
N N1 0.47053(17) 0.95776(12) 0.65239(11) 0.0199(3) Uani d . 1 . .
H H1N 0.4965 1.0218 0.6211 0.024 Uiso d R 1 . .
N N2 0.6661(2) 1.42572(14) 1.02941(12) 0.0305(3) Uani d . 1 . .
N N3 0.28286(18) 0.73684(13) 0.55664(11) 0.0240(3) Uani d . 1 . .
N N4 0.59191(18) 0.74205(13) 0.66231(12) 0.0247(3) Uani d . 1 . .
C C1 0.43680(19) 0.97284(15) 0.75065(13) 0.0200(3) Uani d . 1 . .
C C2 0.48973(19) 1.09818(15) 0.81576(13) 0.0197(3) Uani d . 1 . .
C C3 0.5913(2) 1.19046(16) 0.78890(14) 0.0246(3) Uani d . 1 . .
H H3A 0.6219 1.1794 0.7232 0.030 Uiso calc R 1 . .
C C4 0.6481(2) 1.29926(16) 0.85839(14) 0.0263(4) Uani d . 1 . .
H H4A 0.7182 1.3626 0.8413 0.032 Uiso calc R 1 . .
C C5 0.5999(2) 1.31276(15) 0.95283(13) 0.0232(3) Uani d . 1 . .
C C6 0.4977(2) 1.22431(16) 0.98073(14) 0.0244(3) Uani d . 1 . .
H H6A 0.4653 1.2369 1.0455 0.029 Uiso calc R 1 . .
C C7 0.4429(2) 1.11573(16) 0.91131(13) 0.0229(3) Uani d . 1 . .
H H7A 0.3729 1.0528 0.9292 0.027 Uiso calc R 1 . .
C C8 0.2412(2) 0.65393(18) 0.63379(15) 0.0335(4) Uani d . 1 . .
H H8A 0.1906 0.5735 0.5943 0.050 Uiso calc R 1 . .
H H8B 0.1646 0.6909 0.6668 0.050 Uiso calc R 1 . .
H H8C 0.3405 0.6418 0.6920 0.050 Uiso calc R 1 . .
C C9 0.1508(2) 0.75515(15) 0.45520(13) 0.0217(3) Uani d . 1 . .
H H9A 0.1909 0.8281 0.4217 0.026 Uiso calc R 1 . .
C C10 -0.0048(2) 0.78658(18) 0.47985(15) 0.0306(4) Uani d . 1 . .
H H10A 0.0200 0.8621 0.5318 0.037 Uiso calc R 1 . .
H H10B -0.0464 0.7174 0.5156 0.037 Uiso calc R 1 . .
C C11 -0.1361(2) 0.80878(19) 0.37426(16) 0.0342(4) Uani d . 1 . .
H H11A -0.2379 0.8235 0.3920 0.041 Uiso calc R 1 . .
H H11B -0.0995 0.8839 0.3430 0.041 Uiso calc R 1 . .
C C12 -0.1699(2) 0.69742(19) 0.28905(17) 0.0382(5) Uani d . 1 . .
H H12A -0.2174 0.6243 0.3172 0.046 Uiso calc R 1 . .
H H12B -0.2504 0.7160 0.2202 0.046 Uiso calc R 1 . .
C C13 -0.0139(3) 0.6671(2) 0.26434(16) 0.0393(5) Uani d . 1 . .
H H13A 0.0280 0.7371 0.2296 0.047 Uiso calc R 1 . .
H H13B -0.0382 0.5923 0.2116 0.047 Uiso calc R 1 . .
C C14 0.1171(2) 0.64358(17) 0.37005(15) 0.0297(4) Uani d . 1 . .
H H14A 0.0798 0.5685 0.4010 0.036 Uiso calc R 1 . .
H H14B 0.2189 0.6285 0.3525 0.036 Uiso calc R 1 . .
C C15 0.6164(3) 0.62277(18) 0.61104(17) 0.0404(5) Uani d . 1 . .
H H15A 0.6089 0.5568 0.6597 0.061 Uiso calc R 1 . .
H H15B 0.7243 0.6294 0.5993 0.061 Uiso calc R 1 . .
H H15C 0.5321 0.6029 0.5400 0.061 Uiso calc R 1 . .
C C16 0.7269(2) 0.79996(16) 0.75819(13) 0.0226(3) Uani d . 1 . .
H H16A 0.6797 0.8608 0.7989 0.027 Uiso calc R 1 . .
C C17 0.7955(2) 0.70390(17) 0.83827(14) 0.0279(4) Uani d . 1 . .
H H17A 0.8455 0.6425 0.8016 0.034 Uiso calc R 1 . .
H H17B 0.7059 0.6590 0.8601 0.034 Uiso calc R 1 . .
C C18 0.9245(2) 0.76902(19) 0.94149(15) 0.0329(4) Uani d . 1 . .
H H18A 0.8718 0.8248 0.9816 0.040 Uiso calc R 1 . .
H H18B 0.9714 0.7059 0.9913 0.040 Uiso calc R 1 . .
C C19 1.0606(2) 0.8443(2) 0.91066(16) 0.0363(5) Uani d . 1 . .
H H19A 1.1212 0.7874 0.8780 0.044 Uiso calc R 1 . .
H H19B 1.1380 0.8891 0.9780 0.044 Uiso calc R 1 . .
C C20 0.9923(2) 0.9376(2) 0.82845(17) 0.0361(5) Uani d . 1 . .
H H20A 1.0822 0.9815 0.8063 0.043 Uiso calc R 1 . .
H H20B 0.9424 1.0003 0.8640 0.043 Uiso calc R 1 . .
C C21 0.8637(2) 0.87251(19) 0.72583(15) 0.0306(4) Uani d . 1 . .
H H21A 0.8179 0.9352 0.6752 0.037 Uiso calc R 1 . .
H H21B 0.9156 0.8150 0.6866 0.037 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 P1 N3 . . 109.91(7) ?
O1 P1 N4 . . 117.28(8) ?
N3 P1 N4 . . 105.39(8) ?
O1 P1 N1 . . 106.20(7) ?
N3 P1 N1 . . 113.38(8) ?
N4 P1 N1 . . 104.81(7) ?
C1 N1 P1 . . 125.20(12) ?
C1 N1 H1N . . 120.1 ?
P1 N1 H1N . . 114.6 ?
O4 N2 O3 . . 124.33(16) ?
O4 N2 C5 . . 117.72(15) ?
O3 N2 C5 . . 117.95(16) ?
C8 N3 C9 . . 117.46(14) ?
C8 N3 P1 . . 124.25(12) ?
C9 N3 P1 . . 118.02(11) ?
C15 N4 C16 . . 116.81(14) ?
C15 N4 P1 . . 114.39(12) ?
C16 N4 P1 . . 124.01(11) ?
O2 C1 N1 . . 122.38(15) ?
O2 C1 C2 . . 119.89(15) ?
N1 C1 C2 . . 117.61(14) ?
C3 C2 C7 . . 119.80(15) ?
C3 C2 C1 . . 122.95(15) ?
C7 C2 C1 . . 117.06(15) ?
C2 C3 C4 . . 119.99(16) ?
C2 C3 H3A . . 120.0 ?
C4 C3 H3A . . 120.0 ?
C5 C4 C3 . . 118.47(16) ?
C5 C4 H4A . . 120.8 ?
C3 C4 H4A . . 120.8 ?
C6 C5 C4 . . 122.96(16) ?
C6 C5 N2 . . 118.42(15) ?
C4 C5 N2 . . 118.59(16) ?
C5 C6 C7 . . 118.05(16) ?
C5 C6 H6A . . 121.0 ?
C7 C6 H6A . . 121.0 ?
C6 C7 C2 . . 120.72(16) ?
C6 C7 H7A . . 119.6 ?
C2 C7 H7A . . 119.6 ?
N3 C8 H8A . . 109.5 ?
N3 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
N3 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
N3 C9 C10 . . 112.56(14) ?
N3 C9 C14 . . 111.46(14) ?
C10 C9 C14 . . 111.44(15) ?
N3 C9 H9A . . 107.0 ?
C10 C9 H9A . . 107.0 ?
C14 C9 H9A . . 107.0 ?
C9 C10 C11 . . 111.17(15) ?
C9 C10 H10A . . 109.4 ?
C11 C10 H10A . . 109.4 ?
C9 C10 H10B . . 109.4 ?
C11 C10 H10B . . 109.4 ?
H10A C10 H10B . . 108.0 ?
C12 C11 C10 . . 111.01(16) ?
C12 C11 H11A . . 109.4 ?
C10 C11 H11A . . 109.4 ?
C12 C11 H11B . . 109.4 ?
C10 C11 H11B . . 109.4 ?
H11A C11 H11B . . 108.0 ?
C13 C12 C11 . . 111.06(16) ?
C13 C12 H12A . . 109.4 ?
C11 C12 H12A . . 109.4 ?
C13 C12 H12B . . 109.4 ?
C11 C12 H12B . . 109.4 ?
H12A C12 H12B . . 108.0 ?
C12 C13 C14 . . 111.07(17) ?
C12 C13 H13A . . 109.4 ?
C14 C13 H13A . . 109.4 ?
C12 C13 H13B . . 109.4 ?
C14 C13 H13B . . 109.4 ?
H13A C13 H13B . . 108.0 ?
C9 C14 C13 . . 110.50(15) ?
C9 C14 H14A . . 109.5 ?
C13 C14 H14A . . 109.5 ?
C9 C14 H14B . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 108.1 ?
N4 C15 H15A . . 109.5 ?
N4 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
N4 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
N4 C16 C21 . . 113.46(14) ?
N4 C16 C17 . . 111.50(14) ?
C21 C16 C17 . . 110.48(14) ?
N4 C16 H16A . . 107.0 ?
C21 C16 H16A . . 107.0 ?
C17 C16 H16A . . 107.0 ?
C16 C17 C18 . . 110.00(15) ?
C16 C17 H17A . . 109.7 ?
C18 C17 H17A . . 109.7 ?
C16 C17 H17B . . 109.7 ?
C18 C17 H17B . . 109.7 ?
H17A C17 H17B . . 108.2 ?
C19 C18 C17 . . 111.18(16) ?
C19 C18 H18A . . 109.4 ?
C17 C18 H18A . . 109.4 ?
C19 C18 H18B . . 109.4 ?
C17 C18 H18B . . 109.4 ?
H18A C18 H18B . . 108.0 ?
C18 C19 C20 . . 111.10(16) ?
C18 C19 H19A . . 109.4 ?
C20 C19 H19A . . 109.4 ?
C18 C19 H19B . . 109.4 ?
C20 C19 H19B . . 109.4 ?
H19A C19 H19B . . 108.0 ?
C19 C20 C21 . . 111.01(17) ?
C19 C20 H20A . . 109.4 ?
C21 C20 H20A . . 109.4 ?
C19 C20 H20B . . 109.4 ?
C21 C20 H20B . . 109.4 ?
H20A C20 H20B . . 108.0 ?
C16 C21 C20 . . 110.50(15) ?
C16 C21 H21A . . 109.5 ?
C20 C21 H21A . . 109.5 ?
C16 C21 H21B . . 109.5 ?
C20 C21 H21B . . 109.5 ?
H21A C21 H21B . . 108.1 ?
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 O1 . 1.4834(13) ?
P1 N3 . 1.6315(15) ?
P1 N4 . 1.6446(15) ?
P1 N1 . 1.6859(14) ?
O2 C1 . 1.220(2) ?
O3 N2 . 1.231(2) ?
O4 N2 . 1.219(2) ?
N1 C1 . 1.366(2) ?
N1 H1N . 0.8628 ?
N2 C5 . 1.483(2) ?
N3 C8 . 1.462(2) ?
N3 C9 . 1.489(2) ?
N4 C15 . 1.476(2) ?
N4 C16 . 1.483(2) ?
C1 C2 . 1.513(2) ?
C2 C3 . 1.391(2) ?
C2 C7 . 1.395(2) ?
C3 C4 . 1.395(2) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.383(2) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.374(2) ?
C6 C7 . 1.391(2) ?
C6 H6A . 0.9500 ?
C7 H7A . 0.9500 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 C10 . 1.523(2) ?
C9 C14 . 1.527(2) ?
C9 H9A . 1.0000 ?
C10 C11 . 1.531(3) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.526(3) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.524(3) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 C14 . 1.534(2) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 C21 . 1.525(2) ?
C16 C17 . 1.531(2) ?
C16 H16A . 1.0000 ?
C17 C18 . 1.540(3) ?
C17 H17A . 0.9900 ?
C17 H17B . 0.9900 ?
C18 C19 . 1.524(3) ?
C18 H18A . 0.9900 ?
C18 H18B . 0.9900 ?
C19 C20 . 1.525(3) ?
C19 H19A . 0.9900 ?
C19 H19B . 0.9900 ?
C20 C21 . 1.534(3) ?
C20 H20A . 0.9900 ?
C20 H20B . 0.9900 ?
C21 H21A . 0.9900 ?
C21 H21B . 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 H1N O1 2_676 0.86 1.91 2.7622(18) 167 y
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
O1 P1 N1 C1 . . . . 173.62(13) ?
N3 P1 N1 C1 . . . . 52.83(15) ?
N4 P1 N1 C1 . . . . -61.59(15) ?
O1 P1 N3 C8 . . . . 156.29(15) ?
N4 P1 N3 C8 . . . . 29.03(17) ?
N1 P1 N3 C8 . . . . -85.04(17) ?
O1 P1 N3 C9 . . . . -29.95(15) ?
N4 P1 N3 C9 . . . . -157.20(12) ?
N1 P1 N3 C9 . . . . 88.73(13) ?
O1 P1 N4 C15 . . . . -55.86(16) ?
N3 P1 N4 C15 . . . . 66.78(16) ?
N1 P1 N4 C15 . . . . -173.32(14) ?
O1 P1 N4 C16 . . . . 98.72(15) ?
N3 P1 N4 C16 . . . . -138.64(14) ?
N1 P1 N4 C16 . . . . -18.74(16) ?
P1 N1 C1 O2 . . . . -9.5(2) ?
P1 N1 C1 C2 . . . . 166.63(11) ?
O2 C1 C2 C3 . . . . 166.11(16) ?
N1 C1 C2 C3 . . . . -10.1(2) ?
O2 C1 C2 C7 . . . . -8.9(2) ?
N1 C1 C2 C7 . . . . 174.87(14) ?
C7 C2 C3 C4 . . . . 1.1(3) ?
C1 C2 C3 C4 . . . . -173.82(16) ?
C2 C3 C4 C5 . . . . -0.5(3) ?
C3 C4 C5 C6 . . . . -0.6(3) ?
C3 C4 C5 N2 . . . . 177.27(16) ?
O4 N2 C5 C6 . . . . 168.44(17) ?
O3 N2 C5 C6 . . . . -11.0(2) ?
O4 N2 C5 C4 . . . . -9.5(2) ?
O3 N2 C5 C4 . . . . 171.09(16) ?
C4 C5 C6 C7 . . . . 1.1(3) ?
N2 C5 C6 C7 . . . . -176.72(15) ?
C5 C6 C7 C2 . . . . -0.6(2) ?
C3 C2 C7 C6 . . . . -0.5(2) ?
C1 C2 C7 C6 . . . . 174.68(15) ?
C8 N3 C9 C10 . . . . 49.4(2) ?
P1 N3 C9 C10 . . . . -124.79(14) ?
C8 N3 C9 C14 . . . . -76.7(2) ?
P1 N3 C9 C14 . . . . 109.15(15) ?
N3 C9 C10 C11 . . . . 178.22(15) ?
C14 C9 C10 C11 . . . . -55.7(2) ?
C9 C10 C11 C12 . . . . 55.4(2) ?
C10 C11 C12 C13 . . . . -55.9(2) ?
C11 C12 C13 C14 . . . . 56.5(2) ?
N3 C9 C14 C13 . . . . -177.44(16) ?
C10 C9 C14 C13 . . . . 55.9(2) ?
C12 C13 C14 C9 . . . . -56.2(2) ?
C15 N4 C16 C21 . . . . 81.6(2) ?
P1 N4 C16 C21 . . . . -72.46(19) ?
C15 N4 C16 C17 . . . . -43.9(2) ?
P1 N4 C16 C17 . . . . 162.03(13) ?
N4 C16 C17 C18 . . . . -174.96(15) ?
C21 C16 C17 C18 . . . . 57.9(2) ?
C16 C17 C18 C19 . . . . -56.7(2) ?
C17 C18 C19 C20 . . . . 55.6(2) ?
C18 C19 C20 C21 . . . . -55.6(2) ?
N4 C16 C21 C20 . . . . 175.75(15) ?
C17 C16 C21 C20 . . . . -58.2(2) ?
C19 C20 C21 C16 . . . . 56.9(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745359
2 PubChem 168309858
