##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
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# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-02-24
_journal_date_accepted     2010-03-01
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      4
_journal_page_first     o754
_journal_page_last     o754
_journal_paper_category     QO
_journal_coeditor_code     HG2651
_publ_contact_author
;
     Dr. Seik Weng Ng
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
_publ_contact_author_email     seikweng@um.edu.my
_publ_contact_author_fax     '03 7967 4193'
_publ_contact_author_phone     '03 7967 6778'
_publ_section_title
;
1,3-Dibenzyl-6-bromo-1<i>H</i>-imidazo[4,5-<i>b</i>]pyridin-2(3<i>H</i>)-one
;
loop_
    _publ_author_name
    _publ_author_address
    'Dahmani, S.'
;
Laboratoire de Chimie Organique Appliqu\'ee
Facult\'e des Sciences et Techniques
Universit\'e Sidi Mohamed Ben Abdallah
F\'es
Morocco
;
    'Kandri Rodi, Y.'
;
Laboratoire de Chimie Organique Appliqu\'ee
Facult\'e des Sciences et Techniques
Universit\'e Sidi Mohamed Ben Abdallah
F\'es
Morocco
;
    'Capet, F.'
;
Unit\'e de Catalyse et de Chimie du Solide
Ecole Nationale Sup\'erieure de Chimie de Lille
Lille
France
;
    'Essassi, El Mokhtar'
;
Laboratoire de Chimie Organique H\'et\'erocyclique
P\^ole de Comp\'etences Pharmacochimie
Universit\'e Mohammed V-Agdal
BP 1014 Avenue Ibn Batout
Rabat
Morocco
;
    'Ng, Seik Weng'
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1,3-Dibenzyl-6-bromo-1<i>H</i>-imidazo[4,5-<i>b</i>]pyridin-2(3<i>H</i>)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H16 Br N3 O'
_chemical_formula_sum     'C20 H16 Br N3 O'
_chemical_formula_iupac     'C20 H16 Br N3 O'
_chemical_formula_weight     394.27
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     9.16270(10)
_cell_length_b     25.5071(3)
_cell_length_c     8.06290(10)
_cell_angle_alpha     90.00
_cell_angle_beta     115.5710(10)
_cell_angle_gamma     90.00
_cell_volume     1699.84(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9890
_cell_measurement_theta_min     2.5
_cell_measurement_theta_max     25.0
_cell_measurement_temperature     293(2)
_exptl_crystal_description     Prism
_exptl_crystal_colour     Colorless
_exptl_crystal_size_max     0.42
_exptl_crystal_size_mid     0.18
_exptl_crystal_size_min     0.13
_exptl_crystal_density_diffrn     1.541
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     800
_exptl_absorpt_coefficient_mu     2.431
_exptl_absorpt_correction_type     Multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.4283
_exptl_absorpt_correction_T_max     0.7429
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker X8 APEX2 diffractometer'
_diffrn_measurement_method     '\f and \w scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     38010
_diffrn_reflns_av_R_equivalents     0.0360
_diffrn_reflns_av_sigmaI/netI     0.0206
_diffrn_reflns_theta_min     1.60
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -33
_diffrn_reflns_limit_k_max     33
_diffrn_reflns_limit_l_min     -9
_diffrn_reflns_limit_l_max     10
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     3903
_reflns_number_gt     2967
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0620
_refine_ls_R_factor_gt     0.0408
_refine_ls_wR_factor_gt     0.1160
_refine_ls_wR_factor_ref     0.1380
_refine_ls_goodness_of_fit_ref     1.068
_refine_ls_restrained_S_all     1.068
_refine_ls_number_reflns     3903
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0688P)^2^+1.1691P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.839
_refine_diff_density_min     -0.899
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'Br' 'Br' -0.2901 2.4595
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2008)'
_computing_cell_refinement     'SAINT (Bruker, 2008)'
_computing_data_reduction     'SAINT (Bruker, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'X-SEED (Barbour, 2001)'
_computing_publication_material     'publCIF (Westrip, 2010)'
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
    Br Br1 0.75465(4) 0.225888(14) 0.48173(6) 0.07328(18) Uani d . 1 . .
    O O1 0.2072(3) 0.45942(8) 0.3332(3) 0.0570(5) Uani d . 1 . .
    N N1 0.3210(3) 0.28134(9) 0.4493(3) 0.0480(6) Uani d . 1 . .
    N N2 0.2208(3) 0.36984(9) 0.3920(3) 0.0399(5) Uani d . 1 . .
    N N3 0.4318(3) 0.40833(8) 0.3767(3) 0.0398(5) Uani d . 1 . .
    C C1 0.4498(4) 0.25184(12) 0.4685(4) 0.0515(7) Uani d . 1 . .
    H H1 0.4465 0.2160 0.4879 0.062 Uiso calc R 1 . .
    C C2 0.5858(4) 0.27231(11) 0.4606(4) 0.0473(7) Uani d . 1 . .
    C C3 0.6008(3) 0.32553(11) 0.4321(4) 0.0428(6) Uani d . 1 . .
    H H3 0.6926 0.3396 0.4275 0.051 Uiso calc R 1 . .
    C C4 0.4695(3) 0.35553(10) 0.4115(3) 0.0366(5) Uani d . 1 . .
    C C5 0.3351(3) 0.33129(10) 0.4207(3) 0.0366(5) Uani d . 1 . .
    C C6 0.2777(3) 0.41774(10) 0.3635(4) 0.0401(6) Uani d . 1 . .
    C C7 0.0593(3) 0.36191(13) 0.3822(4) 0.0482(7) Uani d . 1 . .
    H H7A 0.0226 0.3269 0.3356 0.058 Uiso calc R 1 . .
    H H7B -0.0145 0.3867 0.2952 0.058 Uiso calc R 1 . .
    C C8 0.0513(3) 0.36830(10) 0.5637(4) 0.0376(5) Uani d . 1 . .
    C C9 0.0052(3) 0.41597(11) 0.6102(4) 0.0448(6) Uani d . 1 . .
    H H9 -0.0162 0.4444 0.5310 0.054 Uiso calc R 1 . .
    C C10 -0.0090(4) 0.42129(13) 0.7723(4) 0.0530(7) Uani d . 1 . .
    H H10 -0.0399 0.4533 0.8023 0.064 Uiso calc R 1 . .
    C C11 0.0223(4) 0.37940(15) 0.8905(4) 0.0572(8) Uani d . 1 . .
    H H11 0.0105 0.3829 0.9989 0.069 Uiso calc R 1 . .
    C C12 0.0711(4) 0.33231(14) 0.8480(5) 0.0581(8) Uani d . 1 . .
    H H12 0.0946 0.3042 0.9291 0.070 Uiso calc R 1 . .
    C C13 0.0854(3) 0.32658(12) 0.6849(4) 0.0490(7) Uani d . 1 . .
    H H13 0.1180 0.2946 0.6565 0.059 Uiso calc R 1 . .
    C C14 0.5321(4) 0.44829(11) 0.3487(4) 0.0431(6) Uani d . 1 . .
    H H14A 0.6349 0.4498 0.4570 0.052 Uiso calc R 1 . .
    H H14B 0.4797 0.4821 0.3362 0.052 Uiso calc R 1 . .
    C C15 0.5641(3) 0.43916(9) 0.1821(3) 0.0349(5) Uani d . 1 . .
    C C16 0.6900(3) 0.46603(11) 0.1695(4) 0.0437(6) Uani d . 1 . .
    H H16 0.7526 0.4889 0.2630 0.052 Uiso calc R 1 . .
    C C17 0.7240(4) 0.45935(14) 0.0203(4) 0.0549(8) Uani d . 1 . .
    H H17 0.8092 0.4777 0.0137 0.066 Uiso calc R 1 . .
    C C18 0.6319(4) 0.42548(13) -0.1197(4) 0.0533(7) Uani d . 1 . .
    H H18 0.6559 0.4204 -0.2194 0.064 Uiso calc R 1 . .
    C C19 0.5046(4) 0.39937(12) -0.1105(4) 0.0498(7) Uani d . 1 . .
    H H19 0.4411 0.3770 -0.2055 0.060 Uiso calc R 1 . .
    C C20 0.4702(3) 0.40613(11) 0.0401(4) 0.0445(6) Uani d . 1 . .
    H H20 0.3836 0.3884 0.0453 0.053 Uiso calc R 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    Br1 0.0600(2) 0.0554(2) 0.0961(3) 0.01808(15) 0.0259(2) 0.00089(17)
    O1 0.0630(13) 0.0486(12) 0.0681(14) 0.0147(10) 0.0364(11) 0.0062(10)
    N1 0.0528(14) 0.0437(13) 0.0526(14) -0.0072(10) 0.0274(12) 0.0003(10)
    N2 0.0410(11) 0.0455(12) 0.0394(12) -0.0017(9) 0.0233(10) -0.0020(9)
    N3 0.0454(12) 0.0371(11) 0.0455(12) -0.0015(9) 0.0277(10) 0.0009(9)
    C1 0.0595(18) 0.0372(15) 0.0584(18) -0.0029(13) 0.0261(15) 0.0018(13)
    C2 0.0459(15) 0.0424(15) 0.0494(16) 0.0071(12) 0.0166(13) -0.0007(12)
    C3 0.0398(13) 0.0436(14) 0.0478(15) 0.0001(11) 0.0214(12) -0.0026(12)
    C4 0.0424(13) 0.0371(12) 0.0336(12) -0.0029(10) 0.0194(11) -0.0028(10)
    C5 0.0392(13) 0.0400(13) 0.0336(12) -0.0026(10) 0.0186(10) -0.0031(10)
    C6 0.0482(15) 0.0438(14) 0.0346(13) 0.0014(12) 0.0239(11) -0.0020(11)
    C7 0.0359(13) 0.0663(19) 0.0426(15) -0.0056(12) 0.0172(12) -0.0081(13)
    C8 0.0291(11) 0.0463(14) 0.0404(13) -0.0053(10) 0.0177(10) -0.0025(11)
    C9 0.0402(14) 0.0445(15) 0.0506(16) 0.0020(11) 0.0204(12) 0.0050(12)
    C10 0.0482(16) 0.0594(18) 0.0570(18) 0.0009(14) 0.0279(14) -0.0135(15)
    C11 0.0468(16) 0.090(2) 0.0415(16) -0.0001(16) 0.0251(13) -0.0038(16)
    C12 0.0531(18) 0.069(2) 0.0566(19) 0.0009(15) 0.0276(15) 0.0177(16)
    C13 0.0460(15) 0.0441(15) 0.0637(18) 0.0007(12) 0.0302(14) 0.0014(13)
    C14 0.0544(16) 0.0379(13) 0.0447(15) -0.0103(12) 0.0287(13) -0.0057(11)
    C15 0.0382(12) 0.0309(12) 0.0383(13) 0.0023(10) 0.0190(11) 0.0031(10)
    C16 0.0412(14) 0.0442(15) 0.0437(15) -0.0059(11) 0.0166(12) 0.0001(11)
    C17 0.0486(17) 0.066(2) 0.0605(19) -0.0051(14) 0.0338(16) 0.0068(15)
    C18 0.0600(18) 0.0642(19) 0.0467(16) 0.0081(15) 0.0333(15) 0.0053(14)
    C19 0.0571(17) 0.0519(16) 0.0401(15) -0.0015(13) 0.0206(13) -0.0074(12)
    C20 0.0460(15) 0.0461(15) 0.0463(15) -0.0085(12) 0.0245(13) -0.0048(12)
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
    Br1 C2 . 1.897(3) ?
    O1 C6 . 1.213(3) ?
    N1 C5 . 1.311(3) ?
    N1 C1 . 1.351(4) ?
    N2 C5 . 1.382(3) ?
    N2 C6 . 1.386(3) ?
    N2 C7 . 1.462(3) ?
    N3 C4 . 1.389(3) ?
    N3 C6 . 1.391(3) ?
    N3 C14 . 1.453(3) ?
    C1 C2 . 1.377(4) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.393(4) ?
    C3 C4 . 1.374(4) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.408(4) ?
    C7 C8 . 1.505(4) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 C13 . 1.386(4) ?
    C8 C9 . 1.390(4) ?
    C9 C10 . 1.376(4) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.377(5) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.376(5) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.384(5) ?
    C12 H12 . 0.9300 ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.512(4) ?
    C14 H14A . 0.9700 ?
    C14 H14B . 0.9700 ?
    C15 C20 . 1.382(4) ?
    C15 C16 . 1.383(4) ?
    C16 C17 . 1.377(4) ?
    C16 H16 . 0.9300 ?
    C17 C18 . 1.382(5) ?
    C17 H17 . 0.9300 ?
    C18 C19 . 1.372(5) ?
    C18 H18 . 0.9300 ?
    C19 C20 . 1.391(4) ?
    C19 H19 . 0.9300 ?
    C20 H20 . 0.9300 ?
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
    C5 N1 C1 . . 114.4(2) ?
    C5 N2 C6 . . 110.0(2) ?
    C5 N2 C7 . . 126.0(2) ?
    C6 N2 C7 . . 123.9(2) ?
    C4 N3 C6 . . 109.8(2) ?
    C4 N3 C14 . . 126.4(2) ?
    C6 N3 C14 . . 123.8(2) ?
    N1 C1 C2 . . 123.1(3) ?
    N1 C1 H1 . . 118.4 ?
    C2 C1 H1 . . 118.4 ?
    C1 C2 C3 . . 122.2(3) ?
    C1 C2 Br1 . . 118.6(2) ?
    C3 C2 Br1 . . 119.2(2) ?
    C4 C3 C2 . . 114.8(3) ?
    C4 C3 H3 . . 122.6 ?
    C2 C3 H3 . . 122.6 ?
    C3 C4 N3 . . 133.9(2) ?
    C3 C4 C5 . . 119.3(2) ?
    N3 C4 C5 . . 106.9(2) ?
    N1 C5 N2 . . 126.6(2) ?
    N1 C5 C4 . . 126.2(3) ?
    N2 C5 C4 . . 107.2(2) ?
    O1 C6 N2 . . 126.9(3) ?
    O1 C6 N3 . . 127.0(3) ?
    N2 C6 N3 . . 106.1(2) ?
    N2 C7 C8 . . 113.9(2) ?
    N2 C7 H7A . . 108.8 ?
    C8 C7 H7A . . 108.8 ?
    N2 C7 H7B . . 108.8 ?
    C8 C7 H7B . . 108.8 ?
    H7A C7 H7B . . 107.7 ?
    C13 C8 C9 . . 118.9(2) ?
    C13 C8 C7 . . 120.7(3) ?
    C9 C8 C7 . . 120.3(3) ?
    C10 C9 C8 . . 120.4(3) ?
    C10 C9 H9 . . 119.8 ?
    C8 C9 H9 . . 119.8 ?
    C9 C10 C11 . . 120.3(3) ?
    C9 C10 H10 . . 119.9 ?
    C11 C10 H10 . . 119.9 ?
    C12 C11 C10 . . 119.9(3) ?
    C12 C11 H11 . . 120.1 ?
    C10 C11 H11 . . 120.1 ?
    C11 C12 C13 . . 120.2(3) ?
    C11 C12 H12 . . 119.9 ?
    C13 C12 H12 . . 119.9 ?
    C12 C13 C8 . . 120.2(3) ?
    C12 C13 H13 . . 119.9 ?
    C8 C13 H13 . . 119.9 ?
    N3 C14 C15 . . 114.1(2) ?
    N3 C14 H14A . . 108.7 ?
    C15 C14 H14A . . 108.7 ?
    N3 C14 H14B . . 108.7 ?
    C15 C14 H14B . . 108.7 ?
    H14A C14 H14B . . 107.6 ?
    C20 C15 C16 . . 118.8(2) ?
    C20 C15 C14 . . 122.7(2) ?
    C16 C15 C14 . . 118.5(2) ?
    C17 C16 C15 . . 120.9(3) ?
    C17 C16 H16 . . 119.6 ?
    C15 C16 H16 . . 119.6 ?
    C16 C17 C18 . . 120.1(3) ?
    C16 C17 H17 . . 120.0 ?
    C18 C17 H17 . . 120.0 ?
    C19 C18 C17 . . 119.6(3) ?
    C19 C18 H18 . . 120.2 ?
    C17 C18 H18 . . 120.2 ?
    C18 C19 C20 . . 120.3(3) ?
    C18 C19 H19 . . 119.8 ?
    C20 C19 H19 . . 119.8 ?
    C15 C20 C19 . . 120.3(3) ?
    C15 C20 H20 . . 119.9 ?
    C19 C20 H20 . . 119.9 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C5 N1 C1 C2 . . . . 0.6(4) ?
    N1 C1 C2 C3 . . . . 0.0(5) ?
    N1 C1 C2 Br1 . . . . -178.0(2) ?
    C1 C2 C3 C4 . . . . -0.4(4) ?
    Br1 C2 C3 C4 . . . . 177.6(2) ?
    C2 C3 C4 N3 . . . . -178.0(3) ?
    C2 C3 C4 C5 . . . . 0.1(4) ?
    C6 N3 C4 C3 . . . . 178.2(3) ?
    C14 N3 C4 C3 . . . . 0.9(5) ?
    C6 N3 C4 C5 . . . . -0.1(3) ?
    C14 N3 C4 C5 . . . . -177.4(2) ?
    C1 N1 C5 N2 . . . . 178.3(3) ?
    C1 N1 C5 C4 . . . . -1.0(4) ?
    C6 N2 C5 N1 . . . . -178.9(3) ?
    C7 N2 C5 N1 . . . . -2.1(4) ?
    C6 N2 C5 C4 . . . . 0.5(3) ?
    C7 N2 C5 C4 . . . . 177.3(2) ?
    C3 C4 C5 N1 . . . . 0.6(4) ?
    N3 C4 C5 N1 . . . . 179.2(3) ?
    C3 C4 C5 N2 . . . . -178.8(2) ?
    N3 C4 C5 N2 . . . . -0.2(3) ?
    C5 N2 C6 O1 . . . . 179.4(3) ?
    C7 N2 C6 O1 . . . . 2.6(4) ?
    C5 N2 C6 N3 . . . . -0.5(3) ?
    C7 N2 C6 N3 . . . . -177.4(2) ?
    C4 N3 C6 O1 . . . . -179.6(3) ?
    C14 N3 C6 O1 . . . . -2.2(4) ?
    C4 N3 C6 N2 . . . . 0.4(3) ?
    C14 N3 C6 N2 . . . . 177.7(2) ?
    C5 N2 C7 C8 . . . . 92.2(3) ?
    C6 N2 C7 C8 . . . . -91.5(3) ?
    N2 C7 C8 C13 . . . . -86.0(3) ?
    N2 C7 C8 C9 . . . . 95.7(3) ?
    C13 C8 C9 C10 . . . . -1.1(4) ?
    C7 C8 C9 C10 . . . . 177.2(3) ?
    C8 C9 C10 C11 . . . . 0.0(4) ?
    C9 C10 C11 C12 . . . . 1.3(5) ?
    C10 C11 C12 C13 . . . . -1.4(5) ?
    C11 C12 C13 C8 . . . . 0.3(5) ?
    C9 C8 C13 C12 . . . . 1.0(4) ?
    C7 C8 C13 C12 . . . . -177.3(3) ?
    C4 N3 C14 C15 . . . . 62.6(4) ?
    C6 N3 C14 C15 . . . . -114.3(3) ?
    N3 C14 C15 C20 . . . . 18.6(4) ?
    N3 C14 C15 C16 . . . . -163.1(2) ?
    C20 C15 C16 C17 . . . . -1.3(4) ?
    C14 C15 C16 C17 . . . . -179.7(3) ?
    C15 C16 C17 C18 . . . . 0.1(5) ?
    C16 C17 C18 C19 . . . . 1.2(5) ?
    C17 C18 C19 C20 . . . . -1.2(5) ?
    C16 C15 C20 C19 . . . . 1.4(4) ?
    C14 C15 C20 C19 . . . . 179.7(3) ?
    C18 C19 C20 C15 . . . . -0.1(5) ?