#------------------------------------------------------------------------------
#$Date: 2019-09-04 09:39:57 +0200 (Wed 04 de Sep de 2019) $
#$Revision: 217977 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/36/7233648.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_7233648
loop_
_publ_author_name
'Guo-Ping Yong'
'Yu-Mei Zhao'
'Ya Feng'
_publ_section_title
;
 Stimuli-responsive switching of magnetic properties and solid-state
 colors for 2,3'-biimidazo[1,2-a]pyridin-2'-one radical derivatives
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              2228
_journal_page_last               2234
_journal_paper_doi               10.1039/C3TC32130D
_journal_volume                  2
_journal_year                    2014
_chemical_formula_sum            'C22 H20 Cl3 N5 O15'
_chemical_formula_weight         700.78
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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                111.421(5)
_cell_angle_beta                 104.571(5)
_cell_angle_gamma                94.943(6)
_cell_formula_units_Z            2
_cell_length_a                   8.4405(6)
_cell_length_b                   12.6053(7)
_cell_length_c                   14.5536(7)
_cell_measurement_reflns_used    4114
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      69.8219
_cell_measurement_theta_min      3.8396
_cell_volume                     1367.59(16)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0435
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10248
_diffrn_reflns_theta_full        65.07
_diffrn_reflns_theta_max         65.07
_diffrn_reflns_theta_min         3.84
_exptl_absorpt_coefficient_mu    3.822
_exptl_absorpt_correction_T_max  0.3935
_exptl_absorpt_correction_T_min  0.3399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     412
_refine_ls_number_reflns         4528
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0644
_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)+(0.0625P)²+1.7628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1557
_refine_ls_wR_factor_ref         0.1645
_reflns_number_gt                3712
_reflns_number_total             4528
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1000002.cif
_cod_data_source_block           PCOD1000002
_cod_original_cell_volume        1367.59(14)
_cod_database_code               7233648
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.12945(14) 0.80353(9) 1.22897(9) 0.0645(3) Uani 1 1 d . . .
Cl2 Cl -0.24851(14) 0.11566(8) 0.36497(8) 0.0617(3) Uani 1 1 d . . .
Cl3 Cl 1.20796(13) 1.31813(10) 1.25517(8) 0.0637(3) Uani 1 1 d . . .
O6 O 0.1770(4) 0.6931(3) 1.2139(3) 0.0857(10) Uani 1 1 d . . .
N3 N 0.2413(4) 0.5514(2) 0.7280(2) 0.0444(7) Uani 1 1 d . . .
C13 C 0.2386(6) 0.4757(4) 0.5550(3) 0.0598(10) Uani 1 1 d . . .
H13 H 0.2833 0.4784 0.5035 0.072 Uiso 1 1 calc R . .
O1 O 0.5206(4) 0.5774(2) 1.1781(2) 0.0677(8) Uani 1 1 d . . .
N4 N 0.0739(4) 0.4817(3) 0.7938(3) 0.0628(9) Uani 1 1 d . . .
H4 H -0.0032 0.4380 0.8001 0.075 Uiso 1 1 calc R . .
N1 N 0.6319(4) 0.8641(2) 1.0027(2) 0.0435(7) Uani 1 1 d . . .
O2 O 0.1724(4) 0.6184(3) 0.9677(2) 0.0771(9) Uani 1 1 d . . .
H2 H 0.0970 0.5767 0.9721 0.116 Uiso 1 1 calc RD . .
N2 N 0.4533(4) 0.8039(2) 0.8480(2) 0.0460(7) Uani 1 1 d . . .
H2A H 0.3986 0.8005 0.7882 0.055 Uiso 1 1 calc R . .
O3 O 0.0516(8) 0.8003(5) 1.1301(4) 0.145(2) Uani 1 1 d . . .
O9 O -0.2568(5) 0.2221(3) 0.3525(3) 0.0963(13) Uani 1 1 d . . .
C10 C 0.1083(5) 0.4659(3) 0.7046(3) 0.0539(9) Uani 1 1 d . . .
O15 O -0.1589(5) 0.5592(4) 0.9515(4) 0.1014(12) Uani 1 1 d D . .
O12 O 1.0497(5) 1.3072(4) 1.2711(4) 0.1057(13) Uani 1 1 d . . .
C17 C 0.5681(5) 0.6822(3) 1.2185(3) 0.0514(9) Uani 1 1 d . . .
O14 O 1.3105(6) 1.2549(5) 1.2975(3) 0.1139(15) Uani 1 1 d . . .
C8 C 0.2877(5) 0.6225(3) 0.8338(3) 0.0462(8) Uani 1 1 d . . .
C2 C 0.6631(5) 0.9881(3) 0.9131(3) 0.0535(9) Uani 1 1 d . . .
H2B H 0.6293 1.0052 0.8550 0.064 Uiso 1 1 calc R . .
O11 O 1.1869(7) 1.2742(5) 1.1495(3) 0.1241(17) Uani 1 1 d . . .
C18 C 0.6025(5) 0.7449(3) 1.3336(3) 0.0502(9) Uani 1 1 d . . .
C6 C 0.5322(4) 0.7592(3) 0.9841(3) 0.0436(8) Uani 1 1 d . . .
N5 N 0.6539(6) 0.8533(4) 1.5394(3) 0.0869(13) Uani 1 1 d . . .
H5 H 0.6678 0.8889 1.6046 0.104 Uiso 1 1 calc R . .
O8 O -0.3957(6) 0.0364(3) 0.3014(4) 0.1264(19) Uani 1 1 d . . .
C11 C 0.0347(5) 0.3832(3) 0.6049(3) 0.0614(11) Uani 1 1 d . . .
H11 H -0.0555 0.3252 0.5897 0.074 Uiso 1 1 calc R . .
C1 C 0.5814(5) 0.8891(3) 0.9169(3) 0.0449(8) Uani 1 1 d . . .
C7 C 0.4223(4) 0.7228(3) 0.8869(3) 0.0436(8) Uani 1 1 d . . .
C14 C 0.3093(5) 0.5549(3) 0.6535(3) 0.0511(9) Uani 1 1 d . . .
H14 H 0.4029 0.6108 0.6701 0.061 Uiso 1 1 calc R . .
C3 C 0.7930(5) 1.0583(4) 0.9966(3) 0.0602(10) Uani 1 1 d . . .
H3 H 0.8474 1.1258 0.9969 0.072 Uiso 1 1 calc R . .
O4 O 0.0158(7) 0.8198(5) 1.2845(4) 0.1308(18) Uani 1 1 d . . .
C19 C 0.5112(6) 0.6997(4) 1.3825(3) 0.0632(11) Uani 1 1 d . . .
H19 H 0.4318 0.6312 1.3447 0.076 Uiso 1 1 calc R . .
O13 O 1.2809(7) 1.4350(4) 1.3035(5) 0.162(2) Uani 1 1 d . . .
C4 C 0.8460(5) 1.0296(4) 1.0827(3) 0.0618(11) Uani 1 1 d . . .
H4A H 0.9369 1.0776 1.1388 0.074 Uiso 1 1 calc R . .
C5 C 0.7665(5) 0.9331(3) 1.0850(3) 0.0541(9) Uani 1 1 d . . .
H5A H 0.8029 0.9141 1.1418 0.065 Uiso 1 1 calc R . .
C20 C 0.5386(7) 0.7561(5) 1.4863(4) 0.0835(15) Uani 1 1 d . . .
H20 H 0.4773 0.7270 1.5197 0.100 Uiso 1 1 calc R . .
O5 O 0.2678(7) 0.8917(4) 1.2794(6) 0.163(2) Uani 1 1 d . . .
O10 O -0.1147(7) 0.0686(5) 0.3363(4) 0.1315(17) Uani 1 1 d . . .
C16 C 0.5848(5) 0.7530(3) 1.1585(3) 0.0533(9) Uani 1 1 d . . .
H16 H 0.6268 0.8326 1.1927 0.064 Uiso 1 1 calc R . .
C15 C 0.5400(5) 0.7030(3) 1.0561(3) 0.0485(8) Uani 1 1 d . . .
H15 H 0.5098 0.6223 1.0266 0.058 Uiso 1 1 calc R . .
C12 C 0.0990(6) 0.3895(4) 0.5293(3) 0.0648(11) Uani 1 1 d . . .
H12 H 0.0503 0.3368 0.4610 0.078 Uiso 1 1 calc R . .
C22 C 0.7234(6) 0.8440(4) 1.3924(3) 0.0599(10) Uani 1 1 d . . .
H22 H 0.7879 0.8742 1.3611 0.072 Uiso 1 1 calc R . .
C9 C 0.1797(5) 0.5775(3) 0.8723(3) 0.0568(10) Uani 1 1 d . . .
O7 O -0.2189(7) 0.1362(4) 0.4686(3) 0.1222(18) Uani 1 1 d . . .
C21 C 0.7491(7) 0.8983(4) 1.4968(4) 0.0771(13) Uani 1 1 d . . .
H21 H 0.8311 0.9650 1.5372 0.092 Uiso 1 1 calc R . .
H15B H -0.134(3) 0.629(2) 0.997(4) 0.116 Uiso 1 1 d D . .
H15A H -0.252(4) 0.526(3) 0.949(4) 0.116 Uiso 1 1 d D . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
O5 Cl1 O4 110.6(4) . .
O5 Cl1 O3 110.1(4) . .
O4 Cl1 O3 108.8(4) . .
O5 Cl1 O6 110.3(3) . .
O4 Cl1 O6 109.9(3) . .
O3 Cl1 O6 107.1(3) . .
O7 Cl2 O8 112.9(3) . .
O7 Cl2 O10 106.4(3) . .
O8 Cl2 O10 108.2(3) . .
O7 Cl2 O9 109.4(2) . .
O8 Cl2 O9 108.7(2) . .
O10 Cl2 O9 111.2(3) . .
O13 Cl3 O11 111.9(4) . .
O13 Cl3 O14 109.6(4) . .
O11 Cl3 O14 107.7(3) . .
O13 Cl3 O12 107.1(3) . .
O11 Cl3 O12 109.2(3) . .
O14 Cl3 O12 111.5(3) . .
C14 N3 C10 120.5(3) . .
C14 N3 C8 130.5(3) . .
C10 N3 C8 109.0(3) . .
C14 C13 C12 121.1(4) . .
C14 C13 H13 119.4 . .
C12 C13 H13 119.4 . .
C10 N4 C9 109.6(3) . .
C10 N4 H4 125.2 . .
C9 N4 H4 125.2 . .
C5 N1 C1 120.8(3) . .
C5 N1 C6 130.5(3) . .
C1 N1 C6 108.6(3) . .
C9 O2 H2 109.5 . .
C1 N2 C7 110.0(3) . .
C1 N2 H2A 125.0 . .
C7 N2 H2A 125.0 . .
N4 C10 N3 107.0(3) . .
N4 C10 C11 131.3(4) . .
N3 C10 C11 121.7(4) . .
H15B O15 H15A 109(3) . .
O1 C17 C16 122.8(4) . .
O1 C17 C18 119.3(3) . .
C16 C17 C18 117.8(3) . .
C9 C8 N3 105.8(3) . .
C9 C8 C7 129.2(3) . .
N3 C8 C7 125.0(3) . .
C3 C2 C1 118.0(4) . .
C3 C2 H2B 121.0 . .
C1 C2 H2B 121.0 . .
C22 C18 C19 118.8(4) . .
C22 C18 C17 122.6(4) . .
C19 C18 C17 118.7(4) . .
C7 C6 N1 106.4(3) . .
C7 C6 C15 127.0(3) . .
N1 C6 C15 126.6(3) . .
C20 N5 C21 123.4(4) . .
C20 N5 H5 118.3 . .
C21 N5 H5 118.3 . .
C12 C11 C10 117.8(4) . .
C12 C11 H11 121.1 . .
C10 C11 H11 121.1 . .
N2 C1 N1 107.1(3) . .
N2 C1 C2 132.1(3) . .
N1 C1 C2 120.8(3) . .
C6 C7 N2 107.9(3) . .
C6 C7 C8 128.0(3) . .
N2 C7 C8 123.9(3) . .
C13 C14 N3 119.0(4) . .
C13 C14 H14 120.5 . .
N3 C14 H14 120.5 . .
C2 C3 C4 120.5(4) . .
C2 C3 H3 119.8 . .
C4 C3 H3 119.8 . .
C20 C19 C18 119.5(5) . .
C20 C19 H19 120.2 . .
C18 C19 H19 120.2 . .
C5 C4 C3 120.8(4) . .
C5 C4 H4A 119.6 . .
C3 C4 H4A 119.6 . .
C4 C5 N1 119.0(4) . .
C4 C5 H5A 120.5 . .
N1 C5 H5A 120.5 . .
N5 C20 C19 119.4(5) . .
N5 C20 H20 120.3 . .
C19 C20 H20 120.3 . .
C15 C16 C17 119.9(4) . .
C15 C16 H16 120.0 . .
C17 C16 H16 120.0 . .
C16 C15 C6 127.7(3) . .
C16 C15 H15 116.1 . .
C6 C15 H15 116.1 . .
C11 C12 C13 119.9(4) . .
C11 C12 H12 120.0 . .
C13 C12 H12 120.0 . .
C21 C22 C18 120.3(4) . .
C21 C22 H22 119.8 . .
C18 C22 H22 119.8 . .
O2 C9 N4 124.0(4) . .
O2 C9 C8 127.4(4) . .
N4 C9 C8 108.6(3) . .
N5 C21 C22 118.4(5) . .
N5 C21 H21 120.8 . .
C22 C21 H21 120.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 O5 1.374(5) .
Cl1 O4 1.385(4) .
Cl1 O3 1.407(5) .
Cl1 O6 1.437(3) .
Cl2 O7 1.385(4) .
Cl2 O8 1.389(4) .
Cl2 O10 1.405(5) .
Cl2 O9 1.423(3) .
Cl3 O13 1.383(5) .
Cl3 O11 1.388(4) .
Cl3 O14 1.404(4) .
Cl3 O12 1.416(4) .
N3 C14 1.360(5) .
N3 C10 1.367(5) .
N3 C8 1.398(5) .
C13 C14 1.352(5) .
C13 C12 1.403(6) .
C13 H13 0.9300 .
O1 C17 1.215(5) .
N4 C10 1.349(5) .
N4 C9 1.362(5) .
N4 H4 0.8600 .
N1 C5 1.366(5) .
N1 C1 1.373(4) .
N1 C6 1.401(4) .
O2 C9 1.313(5) .
O2 H2 0.8200 .
N2 C1 1.340(5) .
N2 C7 1.374(4) .
N2 H2A 0.8600 .
C10 C11 1.382(6) .
O15 H15B 0.850(10) .
O15 H15A 0.846(10) .
C17 C16 1.479(5) .
C17 C18 1.504(5) .
C8 C9 1.366(5) .
C8 C7 1.444(5) .
C2 C3 1.356(6) .
C2 C1 1.398(5) .
C2 H2B 0.9300 .
C18 C22 1.376(6) .
C18 C19 1.387(6) .
C6 C7 1.365(5) .
C6 C15 1.455(5) .
N5 C20 1.330(7) .
N5 C21 1.334(7) .
N5 H5 0.8600 .
C11 C12 1.366(6) .
C11 H11 0.9300 .
C14 H14 0.9300 .
C3 C4 1.406(6) .
C3 H3 0.9300 .
C19 C20 1.360(7) .
C19 H19 0.9300 .
C4 C5 1.354(6) .
C4 H4A 0.9300 .
C5 H5A 0.9300 .
C20 H20 0.9300 .
C16 C15 1.323(5) .
C16 H16 0.9300 .
C15 H15 0.9300 .
C12 H12 0.9300 .
C22 C21 1.369(6) .
C22 H22 0.9300 .
C21 H21 0.9300 .
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
N4 H4 O6 0.86 2.03 2.873(5) 166.9 2_567
N4 H4 Cl1 0.86 2.98 3.710(3) 144.4 2_567
O2 H2 O15 0.82 2.09 2.759(5) 139.2 .
O2 H2 O15 0.82 2.39 2.891(5) 120.5 2_567
N2 H2A O9 0.86 2.00 2.854(4) 174.2 2_566
N2 H2A Cl2 0.86 2.87 3.677(3) 157.7 2_566
N5 H5 O5 0.86 2.58 3.208(7) 130.6 2_678
O15 H15B O3 0.850(10) 2.393(17) 3.183(8) 155(2) .
O15 H15A O1 0.846(10) 2.42(4) 3.109(5) 138(5) 2_567
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
C9 N4 C10 N3 1.6(5) . . . .
C9 N4 C10 C11 -178.7(4) . . . .
C14 N3 C10 N4 177.2(3) . . . .
C8 N3 C10 N4 -0.9(4) . . . .
C14 N3 C10 C11 -2.4(6) . . . .
C8 N3 C10 C11 179.4(4) . . . .
C14 N3 C8 C9 -178.0(4) . . . .
C10 N3 C8 C9 -0.1(4) . . . .
C14 N3 C8 C7 2.7(6) . . . .
C10 N3 C8 C7 -179.4(3) . . . .
O1 C17 C18 C22 148.2(4) . . . .
C16 C17 C18 C22 -35.2(6) . . . .
O1 C17 C18 C19 -30.3(6) . . . .
C16 C17 C18 C19 146.2(4) . . . .
C5 N1 C6 C7 -175.7(4) . . . .
C1 N1 C6 C7 -0.2(4) . . . .
C5 N1 C6 C15 6.6(6) . . . .
C1 N1 C6 C15 -177.8(4) . . . .
N4 C10 C11 C12 -179.7(4) . . . .
N3 C10 C11 C12 -0.2(6) . . . .
C7 N2 C1 N1 -1.3(4) . . . .
C7 N2 C1 C2 177.7(4) . . . .
C5 N1 C1 N2 177.0(3) . . . .
C6 N1 C1 N2 0.9(4) . . . .
C5 N1 C1 C2 -2.2(5) . . . .
C6 N1 C1 C2 -178.2(3) . . . .
C3 C2 C1 N2 -179.0(4) . . . .
C3 C2 C1 N1 -0.1(6) . . . .
N1 C6 C7 N2 -0.6(4) . . . .
C15 C6 C7 N2 177.0(4) . . . .
N1 C6 C7 C8 -176.4(3) . . . .
C15 C6 C7 C8 1.2(6) . . . .
C1 N2 C7 C6 1.2(4) . . . .
C1 N2 C7 C8 177.2(3) . . . .
C9 C8 C7 C6 38.8(7) . . . .
N3 C8 C7 C6 -142.0(4) . . . .
C9 C8 C7 N2 -136.4(4) . . . .
N3 C8 C7 N2 42.7(6) . . . .
C12 C13 C14 N3 -1.1(6) . . . .
C10 N3 C14 C13 3.0(5) . . . .
C8 N3 C14 C13 -179.2(4) . . . .
C1 C2 C3 C4 1.9(6) . . . .
C22 C18 C19 C20 2.4(6) . . . .
C17 C18 C19 C20 -179.0(4) . . . .
C2 C3 C4 C5 -1.5(7) . . . .
C3 C4 C5 N1 -0.8(7) . . . .
C1 N1 C5 C4 2.6(6) . . . .
C6 N1 C5 C4 177.7(4) . . . .
C21 N5 C20 C19 -1.7(9) . . . .
C18 C19 C20 N5 -0.7(8) . . . .
O1 C17 C16 C15 3.1(7) . . . .
C18 C17 C16 C15 -173.3(4) . . . .
C17 C16 C15 C6 173.6(4) . . . .
C7 C6 C15 C16 -147.3(4) . . . .
N1 C6 C15 C16 29.9(7) . . . .
C10 C11 C12 C13 2.1(6) . . . .
C14 C13 C12 C11 -1.5(7) . . . .
C19 C18 C22 C21 -1.9(6) . . . .
C17 C18 C22 C21 179.6(4) . . . .
C10 N4 C9 O2 176.9(4) . . . .
C10 N4 C9 C8 -1.7(5) . . . .
N3 C8 C9 O2 -177.4(4) . . . .
C7 C8 C9 O2 1.8(8) . . . .
N3 C8 C9 N4 1.1(5) . . . .
C7 C8 C9 N4 -179.6(4) . . . .
C20 N5 C21 C22 2.2(8) . . . .
C18 C22 C21 N5 -0.4(7) . . . .
