#------------------------------------------------------------------------------
#$Date: 2020-12-10 05:35:47 +0200 (Thu, 10 Dec 2020) $
#$Revision: 259731 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/17/7241739.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_7241739
loop_
_publ_author_name
'Ye, Yang'
'Gao, Lei'
'Hao, Hongxun'
'Yin, Qiuxiang'
'Xie, Chuang'
_publ_section_title
;
 Tuning the photomechanical behavior and excellent elasticity of
 azobenzene via cocrystal engineering
;
_journal_issue                   46
_journal_name_full               CrystEngComm
_journal_page_first              8045
_journal_page_last               8053
_journal_paper_doi               10.1039/D0CE01394C
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C12 H11 N3, C9 H12 N2'
_chemical_formula_sum            'C21 H23 N5'
_chemical_formula_weight         345.44
_chemical_melting_point          352.12
_chemical_name_systematic        '4-Aminoazobenzene; 4-Pyrrolidinopyridine'
_chemical_properties_physical    Light-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-06-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-06-10 deposited with the CCDC.	2020-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.84(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.9177(16)
_cell_length_b                   5.9154(12)
_cell_length_c                   19.843(4)
_cell_measurement_reflns_used    2790
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9143
_cell_measurement_theta_min      2.0529
_cell_volume                     929.3(3)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      113.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11209
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.883
_diffrn_reflns_theta_min         2.053
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.7556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_preparation       photochromic
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate/n-heptane'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_coef       0.043(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4268
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0471
_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)+(0.0606P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1160
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3075
_reflns_number_total             4268
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01394c3.cif
_cod_data_source_block           shelxl
_cod_database_code               7241739
_shelx_shelxl_version_number     2018/3
_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_max   0.991
_shelx_estimated_absorpt_t_min   0.985
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2. Restrained distances
 H1A-H1B
 1.5 with sigma of 0.01
 N1-H1A = N1-H1B
 0.9 with sigma of 0.01
 H19A-H19B = H19C-H19D
 1.55 with sigma of 0.01
 C19-H19A = C19'-H19B = C19-H19C = C19'-H19D
 0.93 with sigma of 0.05
3. Rigid bond restraints
 N2, C4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Fixed Sof: C19(0.5) H19A(0.5) H19B(0.5) C19'(0.5) H19C(0.5) H19D(0.5)
5.a Riding coordinates:
 C18(H18A,H18B), C20(H20A,H20B)
5.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C16(H16), C17(H17)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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
N1 N 0.5579(3) 0.5979(5) 0.55427(13) 0.0455(6) Uani 1 1 d D . . . .
H1A H 0.639(3) 0.560(5) 0.5247(12) 0.055 Uiso 1 1 d DR . . . .
H1B H 0.516(4) 0.736(3) 0.5478(14) 0.055 Uiso 1 1 d DR . . . .
N2 N 0.4643(3) 0.1261(4) 0.79444(11) 0.0367(5) Uani 1 1 d . U . . .
N3 N 0.3620(3) 0.2075(4) 0.83513(12) 0.0402(6) Uani 1 1 d . . . . .
N4 N -0.1903(3) 0.4387(4) 0.45843(11) 0.0362(6) Uani 1 1 d . . . . .
N5 N 0.0496(3) 0.3167(4) 0.27466(11) 0.0305(5) Uani 1 1 d . . . . .
C1 C 0.5374(3) 0.4906(5) 0.61438(13) 0.0322(6) Uani 1 1 d . . . . .
C2 C 0.6138(3) 0.2807(5) 0.62710(14) 0.0341(6) Uani 1 1 d . . . . .
H2 H 0.684328 0.215229 0.594071 0.041 Uiso 1 1 calc R . . . .
C3 C 0.5880(3) 0.1688(5) 0.68660(13) 0.0336(6) Uani 1 1 d . . . . .
H3 H 0.640435 0.026377 0.694192 0.040 Uiso 1 1 calc R . . . .
C4 C 0.4859(3) 0.2614(5) 0.73595(14) 0.0336(6) Uani 1 1 d . U . . .
C5 C 0.4120(3) 0.4736(5) 0.72460(14) 0.0349(6) Uani 1 1 d . . . . .
H5 H 0.343892 0.539733 0.758337 0.042 Uiso 1 1 calc R . . . .
C6 C 0.4371(3) 0.5868(5) 0.66522(13) 0.0333(6) Uani 1 1 d . . . . .
H6 H 0.386649 0.730738 0.658242 0.040 Uiso 1 1 calc R . . . .
C7 C 0.3354(3) 0.0629(5) 0.89345(13) 0.0360(6) Uani 1 1 d . . . . .
C8 C 0.4094(3) -0.1473(6) 0.90411(15) 0.0424(7) Uani 1 1 d . . . . .
H8 H 0.485859 -0.206911 0.872236 0.051 Uiso 1 1 calc R . . . .
C9 C 0.3708(4) -0.2702(6) 0.96173(14) 0.0449(8) Uani 1 1 d . . . . .
H9 H 0.422578 -0.412745 0.969741 0.054 Uiso 1 1 calc R . . . .
C10 C 0.2565(4) -0.1840(6) 1.00735(15) 0.0448(8) Uani 1 1 d . . . . .
H10 H 0.229261 -0.268193 1.046484 0.054 Uiso 1 1 calc R . . . .
C11 C 0.1818(4) 0.0252(5) 0.99598(15) 0.0446(8) Uani 1 1 d . . . . .
H11 H 0.103775 0.084608 1.027277 0.054 Uiso 1 1 calc R . . . .
C12 C 0.2214(3) 0.1454(5) 0.93936(13) 0.0388(7) Uani 1 1 d . . . . .
H12 H 0.169541 0.287980 0.931537 0.047 Uiso 1 1 calc R . . . .
C13 C -0.1014(3) 0.2487(5) 0.44651(14) 0.0371(7) Uani 1 1 d . . . . .
H13 H -0.096952 0.138335 0.481263 0.044 Uiso 1 1 calc R . . . .
C14 C -0.0170(3) 0.2020(5) 0.38837(13) 0.0335(6) Uani 1 1 d . . . . .
H14 H 0.044337 0.064841 0.384129 0.040 Uiso 1 1 calc R . . . .
C15 C -0.0216(3) 0.3585(4) 0.33497(13) 0.0276(6) Uani 1 1 d . . . . .
C16 C -0.1063(3) 0.5621(4) 0.34802(13) 0.0324(6) Uani 1 1 d . . . . .
H16 H -0.108700 0.678909 0.315161 0.039 Uiso 1 1 calc R . . . .
C17 C -0.1859(3) 0.5918(5) 0.40855(13) 0.0349(6) Uani 1 1 d . . . . .
H17 H -0.242080 0.731578 0.415605 0.042 Uiso 1 1 calc R . . . .
C18 C 0.1159(4) 0.0950(5) 0.25564(14) 0.0397(7) Uani 1 1 d . . . . .
H18A H 0.033564 -0.026164 0.265433 0.048 Uiso 1 1 d R . . A .
H18B H 0.223064 0.062466 0.280072 0.048 Uiso 1 1 d R . . . .
C19 C 0.1866(11) 0.1267(18) 0.1869(5) 0.047(2) Uani 0.5 1 d D . P A 1
H19A H 0.209(8) -0.005(11) 0.160(4) 0.056 Uiso 0.5 1 d DR . P B 1
H19B H 0.306(8) 0.195(9) 0.192(3) 0.056 Uiso 0.5 1 d DR . P C 1
C19' C 0.0996(11) 0.1006(17) 0.1784(4) 0.047(2) Uani 0.5 1 d D . P A 2
H19C H 0.157(6) -0.018(15) 0.154(5) 0.056 Uiso 0.5 1 d DR . P D 2
H19D H -0.022(6) 0.081(12) 0.164(3) 0.056 Uiso 0.5 1 d DR . P E 2
C20 C 0.1035(5) 0.3342(6) 0.15910(16) 0.0612(10) Uani 1 1 d . . . . .
H20A H 0.018481 0.325107 0.122098 0.073 Uiso 1 1 d R . . A .
H20B H 0.205911 0.408397 0.141558 0.073 Uiso 1 1 d R . . . .
C21 C 0.0351(4) 0.4686(5) 0.21656(13) 0.0390(7) Uani 1 1 d . . . . .
H21A H 0.102324 0.607716 0.224049 0.047 Uiso 1 1 calc R . . . .
H21B H -0.084134 0.511101 0.207858 0.047 Uiso 1 1 calc R . . . .
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'
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
H1A N1 H1B 113.5(19) . . ?
C1 N1 H1A 123.2(18) . . ?
C1 N1 H1B 120.4(17) . . ?
N3 N2 C4 113.4(2) . . ?
N2 N3 C7 113.0(2) . . ?
C17 N4 C13 114.4(2) . . ?
C15 N5 C18 123.2(2) . . ?
C15 N5 C21 123.7(2) . . ?
C18 N5 C21 111.8(2) . . ?
N1 C1 C2 120.9(2) . . ?
N1 C1 C6 120.9(3) . . ?
C2 C1 C6 118.2(2) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.9(3) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.7(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 N2 115.5(2) . . ?
C3 C4 C5 119.0(3) . . ?
C5 C4 N2 125.5(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.5(3) . . ?
C5 C6 H6 119.8 . . ?
C8 C7 N3 125.5(3) . . ?
C12 C7 N3 114.9(3) . . ?
C12 C7 C8 119.6(3) . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C9 119.7(3) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.1(3) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.6(3) . . ?
C12 C11 H11 120.2 . . ?
C7 C12 H12 119.4 . . ?
C11 C12 C7 121.2(3) . . ?
C11 C12 H12 119.4 . . ?
N4 C13 H13 117.3 . . ?
N4 C13 C14 125.3(3) . . ?
C14 C13 H13 117.3 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.6(2) . . ?
C15 C14 H14 120.2 . . ?
N5 C15 C14 122.6(2) . . ?
N5 C15 C16 121.7(2) . . ?
C16 C15 C14 115.6(2) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.8(2) . . ?
C17 C16 H16 120.1 . . ?
N4 C17 C16 125.1(3) . . ?
N4 C17 H17 117.5 . . ?
C16 C17 H17 117.5 . . ?
N5 C18 H18A 111.0 . . ?
N5 C18 H18B 110.9 . . ?
N5 C18 C19 105.3(4) . . ?
N5 C18 C19' 102.3(4) . . ?
H18A C18 H18B 109.0 . . ?
C19 C18 H18A 121.8 . . ?
C19 C18 H18B 98.1 . . ?
C19' C18 H18A 99.5 . . ?
C19' C18 H18B 123.5 . . ?
C18 C19 H19A 119(6) . . ?
C18 C19 H19B 108(3) . . ?
C18 C19 C20 105.7(6) . . ?
H19A C19 H19B 101(4) . . ?
C20 C19 H19A 123(6) . . ?
C20 C19 H19B 97(4) . . ?
C18 C19' H19C 117(6) . . ?
C18 C19' H19D 111(3) . . ?
H19C C19' H19D 103(4) . . ?
C20 C19' C18 106.6(6) . . ?
C20 C19' H19C 123(6) . . ?
C20 C19' H19D 93(4) . . ?
C19 C20 H20A 121.3 . . ?
C19 C20 H20B 97.8 . . ?
C19 C20 C21 108.5(4) . . ?
C19' C20 H20A 97.4 . . ?
C19' C20 H20B 122.8 . . ?
C19' C20 C21 107.3(4) . . ?
H20A C20 H20B 108.4 . . ?
C21 C20 H20A 110.2 . . ?
C21 C20 H20B 109.8 . . ?
N5 C21 C20 104.4(2) . . ?
N5 C21 H21A 110.9 . . ?
N5 C21 H21B 110.9 . . ?
C20 C21 H21A 110.9 . . ?
C20 C21 H21B 110.9 . . ?
H21A C21 H21B 108.9 . . ?
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
N1 H1A 0.905(12) . ?
N1 H1B 0.892(12) . ?
N1 C1 1.363(3) . ?
N2 N3 1.248(3) . ?
N2 C4 1.422(3) . ?
N3 C7 1.457(4) . ?
N4 C13 1.349(3) . ?
N4 C17 1.343(3) . ?
N5 C15 1.353(3) . ?
N5 C18 1.464(4) . ?
N5 C21 1.465(3) . ?
C1 C2 1.402(4) . ?
C1 C6 1.413(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.372(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(4) . ?
C4 C5 1.402(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.372(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(4) . ?
C7 C12 1.381(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.393(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.370(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C13 C14 1.370(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.407(3) . ?
C15 C16 1.405(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.376(4) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9901 . ?
C18 H18B 0.9900 . ?
C18 C19 1.493(9) . ?
C18 C19' 1.536(9) . ?
C19 H19A 0.97(5) . ?
C19 H19B 1.03(5) . ?
C19 C20 1.495(10) . ?
C19' H19C 0.97(6) . ?
C19' H19D 1.00(4) . ?
C19' C20 1.435(11) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.497(4) . ?
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_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A N4 0.905(12) 2.030(12) 2.930(3) 173(3) 1_655 yes
C21 H21B N3 0.99 2.62 3.584(4) 164.6 2_556 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -177.5(3) . . . . ?
N1 C1 C6 C5 177.5(3) . . . . ?
N2 N3 C7 C8 -1.7(4) . . . . ?
N2 N3 C7 C12 -179.2(2) . . . . ?
N2 C4 C5 C6 -177.9(2) . . . . ?
N3 N2 C4 C3 -174.9(2) . . . . ?
N3 N2 C4 C5 4.2(4) . . . . ?
N3 C7 C8 C9 -178.9(3) . . . . ?
N3 C7 C12 C11 178.8(3) . . . . ?
N4 C13 C14 C15 -0.9(4) . . . . ?
N5 C15 C16 C17 175.9(2) . . . . ?
N5 C18 C19 C20 -20.5(7) . . . . ?
N5 C18 C19' C20 25.5(6) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C1 C6 C5 -1.7(4) . . . . ?
C2 C3 C4 N2 178.0(2) . . . . ?
C2 C3 C4 C5 -1.2(4) . . . . ?
C3 C4 C5 C6 1.2(4) . . . . ?
C4 N2 N3 C7 177.5(2) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C6 C1 C2 C3 1.8(4) . . . . ?
C7 C8 C9 C10 1.2(4) . . . . ?
C8 C7 C12 C11 1.1(4) . . . . ?
C8 C9 C10 C11 -0.6(5) . . . . ?
C9 C10 C11 C12 0.2(5) . . . . ?
C10 C11 C12 C7 -0.5(5) . . . . ?
C12 C7 C8 C9 -1.5(4) . . . . ?
C13 N4 C17 C16 3.1(4) . . . . ?
C13 C14 C15 N5 -175.6(3) . . . . ?
C13 C14 C15 C16 4.0(4) . . . . ?
C14 C15 C16 C17 -3.6(4) . . . . ?
C15 N5 C18 C19 -178.2(4) . . . . ?
C15 N5 C18 C19' 153.5(4) . . . . ?
C15 N5 C21 C20 -169.5(3) . . . . ?
C15 C16 C17 N4 0.1(4) . . . . ?
C17 N4 C13 C14 -2.6(4) . . . . ?
C18 N5 C15 C14 9.2(4) . . . . ?
C18 N5 C15 C16 -170.4(3) . . . . ?
C18 N5 C21 C20 -2.3(3) . . . . ?
C18 C19 C20 C21 19.8(7) . . . . ?
C18 C19' C20 C21 -28.0(7) . . . . ?
C19 C20 C21 N5 -10.9(5) . . . . ?
C19' C20 C21 N5 19.0(5) . . . . ?
C21 N5 C15 C14 175.0(3) . . . . ?
C21 N5 C15 C16 -4.6(4) . . . . ?
C21 N5 C18 C19 14.5(5) . . . . ?
C21 N5 C18 C19' -13.8(5) . . . . ?
