#------------------------------------------------------------------------------
#$Date: 2023-05-06 13:45:32 +0300 (Sat, 06 May 2023) $
#$Revision: 283580 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/42/2244224.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_2244224
loop_
_publ_author_name
'Herbig, Marcus'
'Böhme, Uwe'
_publ_section_title
;
 Two polymorphs of
 N,N'-diphenyl-2-[1-(propyl-amino)-ethyl-idene]propanedi-amide.
;
_journal_coeditor_code           PK2679
_journal_issue                   'Pt 4'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              308
_journal_page_last               312
_journal_paper_doi               10.1107/S2056989023002141
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C20 H23 N3 O2'
_chemical_formula_moiety         'C20 H23 N3 O2'
_chemical_formula_sum            'C20 H23 N3 O2'
_chemical_formula_weight         337.41
_chemical_name_systematic
;
N,N'-Diphenyl-2-[1-(propylamino)ethylidene]propanediamide
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   27.7071(11)
_cell_length_b                   27.7071(11)
_cell_length_c                   9.4575(4)
_cell_measurement_reflns_used    23893
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.18
_cell_measurement_theta_min      2.71
_cell_volume                     7260.4(5)
_computing_cell_refinement
;
X-AREA (Stoe, 2009)
;
_computing_data_collection
;
X-AREA (Stoe, 2009)
;
_computing_data_reduction
;
X-RED (Stoe, 2009)
;
_computing_molecular_graphics
;
ORTEP3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      193(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            23893
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.911
_diffrn_reflns_theta_min         2.709
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9799
_exptl_absorpt_correction_T_min  0.8437
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
(X-RED; Stoe, 2009)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       Prism
_exptl_crystal_F_000             2880
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.185
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3884
_refine_ls_number_restraints     69
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0516
_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)+(0.0409P)²+6.4556P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1321
_reflns_number_gt                2635
_reflns_number_total             3884
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            pk2679sup1.cif
_cod_data_source_block           II
_cod_depositor_comments
'Adding full bibliography for 2244223--2244224.cif.'
_cod_original_cell_volume        7260.4(7)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               2244224
_cod_database_fobs_code          2244224
_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   0.961
_shelx_estimated_absorpt_t_max   0.980
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+3/4, x+1/4, z+1/4'
'-x+1/2, -y, z+1/2'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'-x+1, -y+1/2, z+1'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'y-3/4, -x-1/4, -z-1/4'
'x-1/2, y, -z-1/2'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'x, y+1/2, -z'
'-y-1/4, x-1/4, -z-1/4'
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
C C1A 0.33034(19) 0.4509(2) 1.0073(5) 0.1009(15) Uani d 0.794(7) A 1
H H1A 0.345612 0.480495 1.042488 0.151 Uiso calc 0.794(7) A 1
H H1B 0.315992 0.433244 1.086538 0.151 Uiso calc 0.794(7) A 1
H H1C 0.305092 0.459356 0.939020 0.151 Uiso calc 0.794(7) A 1
C C2A 0.36613(16) 0.42112(13) 0.9393(4) 0.0792(12) Uani d 0.794(7) A 1
H H2A 0.349729 0.392523 0.898911 0.095 Uiso calc 0.794(7) A 1
H H2B 0.388915 0.409434 1.012267 0.095 Uiso calc 0.794(7) A 1
C C3A 0.39475(11) 0.44513(12) 0.8236(4) 0.0557(9) Uani d 0.794(7) A 1
H H3A 0.416173 0.421327 0.777213 0.067 Uiso calc 0.794(7) A 1
H H3B 0.372703 0.458651 0.751383 0.067 Uiso calc 0.794(7) A 1
C C1B 0.3142(5) 0.4689(5) 0.9652(16) 0.064(4) Uani d 0.206(7) A 2
H H1D 0.335316 0.489802 1.021394 0.095 Uiso calc 0.206(7) A 2
H H1E 0.294887 0.448625 1.028587 0.095 Uiso calc 0.206(7) A 2
H H1F 0.292641 0.488873 0.907398 0.095 Uiso calc 0.206(7) A 2
C C2B 0.3429(5) 0.4388(5) 0.8749(18) 0.082(4) Uani d 0.206(7) A 2
H H2C 0.334739 0.448684 0.777208 0.098 Uiso calc 0.206(7) A 2
H H2D 0.329972 0.405792 0.886790 0.098 Uiso calc 0.206(7) A 2
C C3B 0.3960(4) 0.4337(4) 0.8773(17) 0.060(4) Uani d 0.206(7) A 2
H H3C 0.406400 0.416664 0.790496 0.072 Uiso calc 0.206(7) A 2
H H3D 0.405204 0.413461 0.959305 0.072 Uiso calc 0.206(7) A 2
N N1 0.42335(7) 0.48356(7) 0.8871(2) 0.0554(5) Uani d 1 . .
H H1N 0.4203(8) 0.4899(8) 0.981(3) 0.062(7) Uiso d 1 . .
C C4 0.45371(7) 0.51141(7) 0.8148(2) 0.0489(5) Uani d 1 . .
C C5 0.47728(7) 0.55038(7) 0.8774(2) 0.0441(4) Uani d 1 . .
C C6 0.45777(9) 0.50023(10) 0.6592(2) 0.0673(6) Uani d 1 . .
H H6A 0.474937 0.469611 0.646512 0.101 Uiso calc 1 . .
H H6B 0.475621 0.526138 0.611807 0.101 Uiso calc 1 . .
H H6C 0.425402 0.497686 0.618089 0.101 Uiso calc 1 . .
C C7 0.51595(8) 0.57654(7) 0.8002(2) 0.0503(5) Uani d 1 . .
O O1 0.51926(7) 0.62093(5) 0.79818(17) 0.0724(5) Uani d 1 . .
N N2 0.54997(6) 0.54761(6) 0.73837(19) 0.0496(4) Uani d 1 . .
H H2N 0.5496(8) 0.5170(8) 0.764(2) 0.055(6) Uiso d 1 . .
C C8 0.59020(8) 0.56177(7) 0.6563(2) 0.0486(5) Uani d 1 . .
C C9 0.62718(8) 0.52880(9) 0.6397(2) 0.0607(6) Uani d 1 . .
H H9 0.625036 0.497964 0.683170 0.073 Uiso calc 1 . .
C C10 0.66752(9) 0.54064(11) 0.5594(3) 0.0747(7) Uani d 1 . .
H H10 0.692931 0.517901 0.548843 0.090 Uiso calc 1 . .
C C11 0.67088(10) 0.58508(11) 0.4952(3) 0.0752(7) Uani d 1 . .
H H11 0.698696 0.593338 0.441738 0.090 Uiso calc 1 . .
C C12 0.63374(11) 0.61724(9) 0.5093(3) 0.0758(8) Uani d 1 . .
H H12 0.635694 0.647678 0.463431 0.091 Uiso calc 1 . .
C C13 0.59336(10) 0.60625(8) 0.5892(3) 0.0660(6) Uani d 1 . .
H H13 0.567914 0.629032 0.598067 0.079 Uiso calc 1 . .
C C14 0.46565(7) 0.56580(6) 1.0214(2) 0.0409(4) Uani d 1 . .
O O2 0.43901(5) 0.54185(4) 1.10290(14) 0.0463(3) Uani d 1 . .
N N3 0.48566(6) 0.60834(6) 1.06502(18) 0.0480(4) Uani d 1 . .
H H3N 0.5014(9) 0.6240(9) 0.996(3) 0.069(7) Uiso d 1 . .
C C15 0.48675(7) 0.62908(7) 1.2011(2) 0.0441(4) Uani d 1 . .
C C16 0.51880(8) 0.66737(7) 1.2202(2) 0.0539(5) Uani d 1 . .
H H16 0.538506 0.677647 1.143708 0.065 Uiso calc 1 . .
C C17 0.52215(9) 0.69048(8) 1.3491(3) 0.0652(6) Uani d 1 . .
H H17 0.543793 0.716791 1.360352 0.078 Uiso calc 1 . .
C C18 0.49444(10) 0.67569(9) 1.4611(3) 0.0726(7) Uani d 1 . .
H H18 0.496925 0.691430 1.550003 0.087 Uiso calc 1 . .
C C19 0.46305(10) 0.63785(9) 1.4430(3) 0.0714(7) Uani d 1 . .
H H19 0.443956 0.627485 1.520741 0.086 Uiso calc 1 . .
C C20 0.45852(8) 0.61441(8) 1.3144(2) 0.0556(5) Uani d 1 . .
H H20 0.436309 0.588537 1.303791 0.067 Uiso calc 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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
30 23 7 0.2217
30 -1 2 0.3561
30 22 4 0.3512
28 -18 30 0.9806
-30 -14 -6 0.2011
-30 8 -2 0.4506
10 -30 -1 0.7079
-30 -9 -10 0.3841
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
C2A C1A H1A . . 109.5 ?
C2A C1A H1B . . 109.5 ?
H1A C1A H1B . . 109.5 ?
C2A C1A H1C . . 109.5 ?
H1A C1A H1C . . 109.5 ?
H1B C1A H1C . . 109.5 ?
C1A C2A C3A . . 115.7(3) ?
C1A C2A H2A . . 108.4 ?
C3A C2A H2A . . 108.4 ?
C1A C2A H2B . . 108.4 ?
C3A C2A H2B . . 108.4 ?
H2A C2A H2B . . 107.4 ?
N1 C3A C2A . . 108.1(3) ?
N1 C3A H3A . . 110.1 ?
C2A C3A H3A . . 110.1 ?
N1 C3A H3B . . 110.1 ?
C2A C3A H3B . . 110.1 ?
H3A C3A H3B . . 108.4 ?
C2B C1B H1D . . 109.5 ?
C2B C1B H1E . . 109.5 ?
H1D C1B H1E . . 109.5 ?
C2B C1B H1F . . 109.5 ?
H1D C1B H1F . . 109.5 ?
H1E C1B H1F . . 109.5 ?
C1B C2B C3B . . 126.9(13) ?
C1B C2B H2C . . 105.6 ?
C3B C2B H2C . . 105.6 ?
C1B C2B H2D . . 105.6 ?
C3B C2B H2D . . 105.6 ?
H2C C2B H2D . . 106.1 ?
C2B C3B N1 . . 113.2(10) ?
C2B C3B H3C . . 108.9 ?
N1 C3B H3C . . 108.9 ?
C2B C3B H3D . . 108.9 ?
N1 C3B H3D . . 108.9 ?
H3C C3B H3D . . 107.8 ?
C4 N1 C3A . . 123.8(2) ?
C4 N1 C3B . . 141.3(6) ?
C4 N1 H1N . . 116.8(15) ?
C3A N1 H1N . . 119.5(15) ?
C3B N1 H1N . . 100.4(16) ?
N1 C4 C5 . . 121.78(19) ?
N1 C4 C6 . . 115.5(2) ?
C5 C4 C6 . . 122.6(2) ?
C4 C5 C14 . . 121.24(18) ?
C4 C5 C7 . . 120.47(18) ?
C14 C5 C7 . . 118.27(17) ?
C4 C6 H6A . . 109.5 ?
C4 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C4 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
O1 C7 N2 . . 121.7(2) ?
O1 C7 C5 . . 123.24(19) ?
N2 C7 C5 . . 114.91(17) ?
C7 N2 C8 . . 127.97(18) ?
C7 N2 H2N . . 115.9(14) ?
C8 N2 H2N . . 115.3(14) ?
C9 C8 C13 . . 119.2(2) ?
C9 C8 N2 . . 117.63(18) ?
C13 C8 N2 . . 123.1(2) ?
C8 C9 C10 . . 120.2(2) ?
C8 C9 H9 . . 119.9 ?
C10 C9 H9 . . 119.9 ?
C11 C10 C9 . . 120.4(3) ?
C11 C10 H10 . . 119.8 ?
C9 C10 H10 . . 119.8 ?
C12 C11 C10 . . 119.3(2) ?
C12 C11 H11 . . 120.4 ?
C10 C11 H11 . . 120.4 ?
C11 C12 C13 . . 121.2(2) ?
C11 C12 H12 . . 119.4 ?
C13 C12 H12 . . 119.4 ?
C12 C13 C8 . . 119.7(2) ?
C12 C13 H13 . . 120.1 ?
C8 C13 H13 . . 120.1 ?
O2 C14 N3 . . 120.55(18) ?
O2 C14 C5 . . 123.10(17) ?
N3 C14 C5 . . 116.35(17) ?
C14 N3 C15 . . 129.51(17) ?
C14 N3 H3N . . 113.2(16) ?
C15 N3 H3N . . 117.2(16) ?
C20 C15 C16 . . 118.78(19) ?
C20 C15 N3 . . 125.00(18) ?
C16 C15 N3 . . 116.23(18) ?
C17 C16 C15 . . 120.7(2) ?
C17 C16 H16 . . 119.7 ?
C15 C16 H16 . . 119.7 ?
C18 C17 C16 . . 120.4(2) ?
C18 C17 H17 . . 119.8 ?
C16 C17 H17 . . 119.8 ?
C17 C18 C19 . . 119.2(2) ?
C17 C18 H18 . . 120.4 ?
C19 C18 H18 . . 120.4 ?
C18 C19 C20 . . 121.6(2) ?
C18 C19 H19 . . 119.2 ?
C20 C19 H19 . . 119.2 ?
C19 C20 C15 . . 119.3(2) ?
C19 C20 H20 . . 120.3 ?
C15 C20 H20 . . 120.3 ?
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
C1A C2A . 1.442(6) ?
C1A H1A . 0.9800 ?
C1A H1B . 0.9800 ?
C1A H1C . 0.9800 ?
C2A C3A . 1.506(5) ?
C2A H2A . 0.9900 ?
C2A H2B . 0.9900 ?
C3A N1 . 1.457(3) ?
C3A H3A . 0.9900 ?
C3A H3B . 0.9900 ?
C1B C2B . 1.435(14) ?
C1B H1D . 0.9800 ?
C1B H1E . 0.9800 ?
C1B H1F . 0.9800 ?
C2B C3B . 1.477(14) ?
C2B H2C . 0.9900 ?
C2B H2D . 0.9900 ?
C3B N1 . 1.580(12) ?
C3B H3C . 0.9900 ?
C3B H3D . 0.9900 ?
N1 C4 . 1.331(3) y
N1 H1N . 0.91(2) ?
C4 C5 . 1.394(3) y
C4 C6 . 1.508(3) ?
C5 C14 . 1.463(3) ?
C5 C7 . 1.485(3) ?
C6 H6A . 0.9800 ?
C6 H6B . 0.9800 ?
C6 H6C . 0.9800 ?
C7 O1 . 1.234(2) y
C7 N2 . 1.369(3) y
N2 C8 . 1.414(3) ?
N2 H2N . 0.88(2) ?
C8 C9 . 1.382(3) ?
C8 C13 . 1.389(3) ?
C9 C10 . 1.390(3) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.376(4) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.368(4) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.384(3) ?
C12 H12 . 0.9500 ?
C13 H13 . 0.9500 ?
C14 O2 . 1.257(2) y
C14 N3 . 1.366(2) y
N3 C15 . 1.410(3) ?
N3 H3N . 0.90(3) ?
C15 C20 . 1.387(3) ?
C15 C16 . 1.395(3) ?
C16 C17 . 1.380(3) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.370(4) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.373(4) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.385(3) ?
C19 H19 . 0.9500 ?
C20 H20 . 0.9500 ?
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 O2 . 0.91(2) 1.92(2) 2.638(2) 135(2) yes
N3 H3N O1 . 0.90(3) 1.94(3) 2.712(2) 144(2) yes
C6 H6B N2 . 0.98 2.46 2.968(3) 112.2 yes
C13 H13 O1 . 0.95 2.33 2.879(3) 115.9 yes
C20 H20 O2 . 0.95 2.30 2.887(3) 119.4 yes
N2 H2N O2 9_667 0.88(2) 2.08(2) 2.914(2) 157(2) yes
C9 H9 O2 9_667 0.95 2.91 3.622(3) 132.9 yes
C13 H13 Cg2 1_554 0.95 3.37 3.960(3) 122.2 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
C1A C2A C3A N1 . . . . 65.0(4) y
C1B C2B C3B N1 . . . . -46(2) y
C2A C3A N1 C4 . . . . 178.5(3) ?
C2B C3B N1 C4 . . . . -116.6(12) ?
C3A N1 C4 C5 . . . . 174.5(2) ?
C3B N1 C4 C5 . . . . -166.6(8) ?
C3A N1 C4 C6 . . . . -1.1(3) ?
C3B N1 C4 C6 . . . . 17.9(9) ?
N1 C4 C5 C14 . . . . -7.0(3) ?
C6 C4 C5 C14 . . . . 168.25(18) ?
N1 C4 C5 C7 . . . . 171.42(18) ?
C6 C4 C5 C7 . . . . -13.4(3) ?
C4 C5 C7 O1 . . . . 136.4(2) ?
C14 C5 C7 O1 . . . . -45.1(3) ?
C4 C5 C7 N2 . . . . -47.7(3) ?
C14 C5 C7 N2 . . . . 130.73(19) ?
O1 C7 N2 C8 . . . . -5.4(3) ?
C5 C7 N2 C8 . . . . 178.67(19) ?
C7 N2 C8 C9 . . . . 161.2(2) ?
C7 N2 C8 C13 . . . . -20.8(3) ?
C13 C8 C9 C10 . . . . 1.6(3) ?
N2 C8 C9 C10 . . . . 179.6(2) ?
C8 C9 C10 C11 . . . . -0.4(4) ?
C9 C10 C11 C12 . . . . -1.0(4) ?
C10 C11 C12 C13 . . . . 1.3(4) ?
C11 C12 C13 C8 . . . . -0.2(4) ?
C9 C8 C13 C12 . . . . -1.3(4) ?
N2 C8 C13 C12 . . . . -179.3(2) ?
C4 C5 C14 O2 . . . . 9.5(3) ?
C7 C5 C14 O2 . . . . -168.94(17) ?
C4 C5 C14 N3 . . . . -170.85(17) ?
C7 C5 C14 N3 . . . . 10.7(2) ?
O2 C14 N3 C15 . . . . 9.3(3) ?
C5 C14 N3 C15 . . . . -170.35(18) ?
C14 N3 C15 C20 . . . . -14.1(3) ?
C14 N3 C15 C16 . . . . 166.21(19) ?
C20 C15 C16 C17 . . . . -0.4(3) ?
N3 C15 C16 C17 . . . . 179.2(2) ?
C15 C16 C17 C18 . . . . 0.9(4) ?
C16 C17 C18 C19 . . . . -0.5(4) ?
C17 C18 C19 C20 . . . . -0.3(4) ?
C18 C19 C20 C15 . . . . 0.7(4) ?
C16 C15 C20 C19 . . . . -0.3(3) ?
N3 C15 C20 C19 . . . . 180.0(2) ?
