#------------------------------------------------------------------------------
#$Date: 2021-10-01 01:18:43 +0300 (Fri, 01 Oct 2021) $
#$Revision: 269407 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/47/1564784.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_1564784
loop_
_publ_author_name
'Sadowski, Bartłomiej'
'Kaliszewska, Marzena'
'Poronik, Yevgen M.'
'Czichy, Małgorzata'
'Janasik, Patryk'
'Banasiewicz, Marzena'
'Mierzwa, Dominik'
'Gadomski, Wojciech'
'Lohrey, Trevor D.'
'Clark, John A.'
'Łapkowski, Mieczysław'
'Kozankiewicz, Bolesław'
'Vullev, Valentine I.'
'Sobolewski, Andrzej L.'
'Piatkowski, Piotr'
'Gryko, Daniel T.'
_publ_section_title
;
 Potent strategy towards strongly emissive nitroaromatics through a weakly
 electron-deficient core
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC03670J
_journal_year                    2021
_chemical_formula_moiety         'C42 H46 N4 O6'
_chemical_formula_sum            'C42 H46 N4 O6'
_chemical_formula_weight         702.83
_chemical_name_systematic
6,12-Diheptyl-3,9-bis(2-methyl-4-nitrophenyl)-5H,11H-dipyrrolo[1,2-b:1',2'-g][2,6]naphthyridine-5,11-dione
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2020-07-25 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.544(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.8094(2)
_cell_length_b                   12.3555(4)
_cell_length_c                   31.0929(10)
_cell_measurement_reflns_used    2335
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      68.67
_cell_measurement_theta_min      2.85
_cell_volume                     1844.09(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0849
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            36814
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.675
_diffrn_reflns_theta_min         2.848
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_T_max  0.9270
_exptl_absorpt_correction_T_min  0.8670
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             748
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform/hexane'
_exptl_crystal_size_max          0.215
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.714
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3383
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.1135
_refine_ls_R_factor_gt           0.0821
_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)+(0.1593P)²+1.2976P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2441
_refine_ls_wR_factor_ref         0.2792
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2335
_reflns_number_total             3383
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc03670j2.cif
_cod_data_source_block           BS591_B_0m
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1564784
_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   0.867
_shelx_estimated_absorpt_t_max   0.927
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
O1 O 0.2833(5) 0.4040(2) -0.07476(7) 0.0665(8) Uani 1 1 d . . . . .
O2 O -0.3272(13) 0.8222(4) 0.25138(16) 0.157(2) Uani 1 1 d . . . . .
O3 O -0.5349(10) 0.6872(4) 0.27684(12) 0.1353(17) Uani 1 1 d . . . . .
N1 N 0.0578(5) 0.4713(2) 0.08041(8) 0.0464(7) Uani 1 1 d . . . . .
N2 N -0.3824(10) 0.7284(5) 0.25171(12) 0.0957(13) Uani 1 1 d . . . . .
C1 C 0.0706(7) 0.4574(3) 0.12510(10) 0.0535(8) Uani 1 1 d . . . . .
C2 C 0.2268(9) 0.3669(3) 0.13353(11) 0.0660(10) Uani 1 1 d . . . . .
H2 H 0.2665 0.3372 0.1607 0.079 Uiso 1 1 calc R U . . .
C3 C 0.3179(9) 0.3258(3) 0.09499(11) 0.0639(10) Uani 1 1 d . . . . .
H3 H 0.4298 0.2651 0.0922 0.077 Uiso 1 1 calc R U . . .
C4 C 0.2134(7) 0.3907(2) 0.06194(10) 0.0474(8) Uani 1 1 d . . . . .
C5 C 0.2397(6) 0.3870(2) 0.01646(10) 0.0434(7) Uani 1 1 d . . . . .
C6 C 0.0922(6) 0.4603(2) -0.00924(9) 0.0418(7) Uani 1 1 d . . . . .
C7 C 0.1206(6) 0.4590(2) -0.05624(10) 0.0468(8) Uani 1 1 d . . . . .
C8 C -0.0421(7) 0.5313(3) 0.15689(10) 0.0553(9) Uani 1 1 d . . . . .
C9 C 0.0301(7) 0.6407(3) 0.15989(10) 0.0542(8) Uani 1 1 d . . . . .
C10 C -0.0833(8) 0.7022(3) 0.19211(12) 0.0628(10) Uani 1 1 d . . . . .
C11 C -0.2598(9) 0.6568(4) 0.21956(11) 0.0678(10) Uani 1 1 d . . . . .
C12 C -0.3248(10) 0.5493(4) 0.21873(12) 0.0753(12) Uani 1 1 d . . . . .
C13 C -0.2134(9) 0.4865(3) 0.18719(11) 0.0668(10) Uani 1 1 d . . . . .
C14 C 0.2279(8) 0.6912(3) 0.13127(12) 0.0665(10) Uani 1 1 d . . . . .
H14A H 0.3606 0.6381 0.1231 0.100 Uiso 1 1 calc R U . . .
H14B H 0.3237 0.7495 0.1462 0.100 Uiso 1 1 calc R U . . .
H14C H 0.1275 0.7186 0.1059 0.100 Uiso 1 1 calc R U . . .
C15 C 0.4207(7) 0.2981(3) 0.00063(12) 0.0525(8) Uani 1 1 d . . . . .
C16 C 0.2516(8) 0.2028(3) -0.01744(12) 0.0622(9) Uani 1 1 d . . . . .
H16A H 0.1697 0.1653 0.0061 0.075 Uiso 1 1 calc R U . . .
H16B H 0.1006 0.2299 -0.0366 0.075 Uiso 1 1 calc R U . . .
C17 C 0.4190(13) 0.1241(4) -0.04146(18) 0.1023(18) Uani 1 1 d . . . . .
H17A H 0.5610 0.0931 -0.0216 0.123 Uiso 1 1 calc R U . . .
H17B H 0.5132 0.1630 -0.0634 0.123 Uiso 1 1 calc R U . . .
C18 C 0.253(2) 0.0343(5) -0.0624(3) 0.181(4) Uani 1 1 d D . . . .
H18A H 0.2862 -0.0293 -0.0446 0.218 Uiso 1 1 calc R U . . .
H18B H 0.0585 0.0532 -0.0606 0.218 Uiso 1 1 calc R U . . .
C20 C 0.162(2) -0.0754(8) -0.1278(3) 0.178(4) Uani 1 1 d D . . . .
H20A H 0.0283 -0.1159 -0.1120 0.214 Uiso 1 1 calc R U . . .
H20B H 0.3067 -0.1253 -0.1354 0.214 Uiso 1 1 calc R U . . .
C21 C 0.022(2) -0.0330(8) -0.1671(3) 0.172(3) Uani 1 1 d D . . . .
H21A H -0.1127 0.0202 -0.1599 0.258 Uiso 1 1 calc R U . . .
H21B H -0.0696 -0.0910 -0.1829 0.258 Uiso 1 1 calc R U . . .
H21C H 0.1572 -0.0003 -0.1846 0.258 Uiso 1 1 calc R U . . .
H10 H -0.017(9) 0.777(4) 0.1924(14) 0.091(14) Uiso 1 1 d . . . . .
H13 H -0.226(7) 0.399(3) 0.1893(12) 0.066(10) Uiso 1 1 d . . . . .
H15A H 0.548(7) 0.274(3) 0.0240(11) 0.046(8) Uiso 1 1 d . . . . .
H15B H 0.530(8) 0.323(3) -0.0213(13) 0.064(11) Uiso 1 1 d . . . . .
H12 H -0.473(9) 0.519(4) 0.2391(15) 0.089(13) Uiso 1 1 d . . . . .
C19 C 0.282(3) 0.0052(13) -0.1007(3) 0.279(9) Uani 1 1 d D . . . .
H19A H 0.4800 -0.0082 -0.1014 0.335 Uiso 1 1 calc R U . . .
H19B H 0.2483 0.0712 -0.1171 0.335 Uiso 1 1 calc R U . . .
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'
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
C4 N1 C1 109.3(3) . . ?
C4 N1 C7 123.1(3) . 3_565 ?
C1 N1 C7 126.6(3) . 3_565 ?
O2 N2 O3 123.9(5) . . ?
O2 N2 C11 118.5(4) . . ?
O3 N2 C11 117.6(5) . . ?
C2 C1 N1 106.4(3) . . ?
C2 C1 C8 126.9(3) . . ?
N1 C1 C8 126.5(3) . . ?
C1 C2 C3 109.4(3) . . ?
C1 C2 H2 125.3 . . ?
C3 C2 H2 125.3 . . ?
C4 C3 C2 108.1(3) . . ?
C4 C3 H3 126.0 . . ?
C2 C3 H3 126.0 . . ?
C3 C4 N1 106.9(3) . . ?
C3 C4 C5 132.2(3) . . ?
N1 C4 C5 120.9(3) . . ?
C6 C5 C4 118.7(3) . . ?
C6 C5 C15 125.4(3) . . ?
C4 C5 C15 115.8(3) . . ?
C5 C6 C6 121.1(3) . 3_565 ?
C5 C6 C7 119.4(3) . . ?
C6 C6 C7 119.5(3) 3_565 . ?
O1 C7 N1 118.9(3) . 3_565 ?
O1 C7 C6 125.5(3) . . ?
N1 C7 C6 115.7(3) 3_565 . ?
C9 C8 C13 119.4(3) . . ?
C9 C8 C1 123.0(3) . . ?
C13 C8 C1 117.5(3) . . ?
C10 C9 C8 118.0(3) . . ?
C10 C9 C14 119.7(3) . . ?
C8 C9 C14 122.3(3) . . ?
C11 C10 C9 120.8(4) . . ?
C11 C10 H10 127(3) . . ?
C9 C10 H10 112(3) . . ?
C10 C11 C12 122.7(4) . . ?
C10 C11 N2 117.7(4) . . ?
C12 C11 N2 119.6(4) . . ?
C11 C12 C13 117.5(4) . . ?
C11 C12 H12 120(2) . . ?
C13 C12 H12 122(3) . . ?
C12 C13 C8 121.5(4) . . ?
C12 C13 H13 119(2) . . ?
C8 C13 H13 118(2) . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 C15 C16 112.3(3) . . ?
C5 C15 H15A 109.1(19) . . ?
C16 C15 H15A 110.2(19) . . ?
C5 C15 H15B 111(2) . . ?
C16 C15 H15B 107(2) . . ?
H15A C15 H15B 107(3) . . ?
C17 C16 C15 113.4(3) . . ?
C17 C16 H16A 108.9 . . ?
C15 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C16 C17 C18 114.4(6) . . ?
C16 C17 H17A 108.7 . . ?
C18 C17 H17A 108.7 . . ?
C16 C17 H17B 108.7 . . ?
C18 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C19 C18 C17 122.6(8) . . ?
C19 C18 H18A 106.7 . . ?
C17 C18 H18A 106.7 . . ?
C19 C18 H18B 106.7 . . ?
C17 C18 H18B 106.7 . . ?
H18A C18 H18B 106.6 . . ?
C19 C20 C21 113.5(10) . . ?
C19 C20 H20A 108.9 . . ?
C21 C20 H20A 108.9 . . ?
C19 C20 H20B 108.9 . . ?
C21 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C19 C20 134.8(10) . . ?
C18 C19 H19A 103.5 . . ?
C20 C19 H19A 103.5 . . ?
C18 C19 H19B 103.5 . . ?
C20 C19 H19B 103.5 . . ?
H19A C19 H19B 105.3 . . ?
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
O1 C7 1.209(4) . ?
O2 N2 1.189(6) . ?
O3 N2 1.216(6) . ?
N1 C4 1.392(4) . ?
N1 C1 1.398(4) . ?
N1 C7 1.401(4) 3_565 ?
N2 C11 1.484(5) . ?
C1 C2 1.364(5) . ?
C1 C8 1.473(5) . ?
C2 C3 1.397(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.428(4) . ?
C5 C6 1.376(4) . ?
C5 C15 1.504(4) . ?
C6 C6 1.463(6) 3_565 ?
C6 C7 1.477(4) . ?
C7 N1 1.401(4) 3_565 ?
C8 C9 1.397(5) . ?
C8 C13 1.403(5) . ?
C9 C10 1.396(5) . ?
C9 C14 1.480(5) . ?
C10 C11 1.362(6) . ?
C10 H10 0.98(5) . ?
C11 C12 1.364(6) . ?
C12 C13 1.385(5) . ?
C12 H12 1.05(5) . ?
C13 H13 1.08(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.518(5) . ?
C15 H15A 0.97(3) . ?
C15 H15B 0.94(4) . ?
C16 C17 1.492(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.493(9) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.259(9) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C20 C19 1.404(10) . ?
C20 C21 1.457(10) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
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
C12 H12 O2 1.05(5) 2.63(5) 3.425(7) 132(3) 2_445
C12 H12 O2 1.05(5) 2.63(5) 3.425(7) 132(3) 2_445
C12 H12 O2 1.05(5) 2.63(5) 3.425(7) 132(3) 2_445
C12 H12 O2 1.05(5) 2.63(5) 3.425(7) 132(3) 2_445
C12 H12 O2 1.05(5) 2.63(5) 3.425(7) 132(3) 2_445
C12 H12 O2 1.05(5) 2.63(5) 3.425(7) 132(3) 2_445
C12 H12 O2 1.05(5) 2.63(5) 3.425(7) 132(3) 2_445
C12 H12 O2 1.05(5) 2.63(5) 3.425(7) 132(3) 2_445
C2 H2 O2 0.93 2.74 3.623(6) 159.5 2_545
C2 H2 O3 0.93 2.93 3.793(6) 155.5 2_545
C2 H2 N2 0.93 3.06 3.986(5) 177.0 2_545
C12 H12 O2 1.05(5) 2.63(5) 3.425(7) 132(3) 2_445
C12 H12 O2 1.05(5) 2.63(5) 3.425(7) 132(3) 2_445
C12 H12 O2 1.05(5) 2.63(5) 3.425(7) 132(3) 2_445
C12 H12 O2 1.05(5) 2.63(5) 3.425(7) 132(3) 2_445
C12 H12 O2 1.05(5) 2.63(5) 3.425(7) 132(3) 2_445
C12 H12 O2 1.05(5) 2.63(5) 3.425(7) 132(3) 2_445
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
C4 N1 C1 C2 -1.7(4) . . . . ?
C7 N1 C1 C2 167.2(3) 3_565 . . . ?
C4 N1 C1 C8 173.6(3) . . . . ?
C7 N1 C1 C8 -17.6(5) 3_565 . . . ?
N1 C1 C2 C3 1.6(4) . . . . ?
C8 C1 C2 C3 -173.6(4) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C2 C3 C4 N1 -0.1(4) . . . . ?
C2 C3 C4 C5 179.9(4) . . . . ?
C1 N1 C4 C3 1.1(4) . . . . ?
C7 N1 C4 C3 -168.3(3) 3_565 . . . ?
C1 N1 C4 C5 -178.9(3) . . . . ?
C7 N1 C4 C5 11.7(4) 3_565 . . . ?
C3 C4 C5 C6 175.5(4) . . . . ?
N1 C4 C5 C6 -4.5(4) . . . . ?
C3 C4 C5 C15 -1.9(5) . . . . ?
N1 C4 C5 C15 178.1(3) . . . . ?
C4 C5 C6 C6 -1.0(5) . . . 3_565 ?
C15 C5 C6 C6 176.1(3) . . . 3_565 ?
C4 C5 C6 C7 178.9(3) . . . . ?
C15 C5 C6 C7 -4.0(5) . . . . ?
C5 C6 C7 O1 -6.7(5) . . . . ?
C6 C6 C7 O1 173.3(4) 3_565 . . . ?
C5 C6 C7 N1 173.7(3) . . . 3_565 ?
C6 C6 C7 N1 -6.3(5) 3_565 . . 3_565 ?
C2 C1 C8 C9 118.7(4) . . . . ?
N1 C1 C8 C9 -55.6(5) . . . . ?
C2 C1 C8 C13 -56.6(5) . . . . ?
N1 C1 C8 C13 129.1(4) . . . . ?
C13 C8 C9 C10 -2.9(5) . . . . ?
C1 C8 C9 C10 -178.1(3) . . . . ?
C13 C8 C9 C14 174.9(3) . . . . ?
C1 C8 C9 C14 -0.2(5) . . . . ?
C8 C9 C10 C11 -0.3(5) . . . . ?
C14 C9 C10 C11 -178.2(4) . . . . ?
C9 C10 C11 C12 3.3(6) . . . . ?
C9 C10 C11 N2 -177.2(3) . . . . ?
O2 N2 C11 C10 1.9(7) . . . . ?
O3 N2 C11 C10 -178.3(4) . . . . ?
O2 N2 C11 C12 -178.6(6) . . . . ?
O3 N2 C11 C12 1.1(7) . . . . ?
C10 C11 C12 C13 -2.8(7) . . . . ?
N2 C11 C12 C13 177.7(4) . . . . ?
C11 C12 C13 C8 -0.6(6) . . . . ?
C9 C8 C13 C12 3.4(6) . . . . ?
C1 C8 C13 C12 178.9(4) . . . . ?
C6 C5 C15 C16 -77.0(4) . . . . ?
C4 C5 C15 C16 100.2(3) . . . . ?
C5 C15 C16 C17 168.1(4) . . . . ?
C15 C16 C17 C18 -175.5(5) . . . . ?
C16 C17 C18 C19 133.8(13) . . . . ?
C17 C18 C19 C20 178.5(15) . . . . ?
C21 C20 C19 C18 121(2) . . . . ?
