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#$Date: 2024-08-05 23:00:39 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293941 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/00/7160049.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_7160049
loop_
_publ_author_name
'Brown, Emily B.'
'Gapare, Rosinah Liandrah'
'Campbell, Jacob W.'
'Alkaş, Adil'
'Sequeira, Steve'
'Hilborn, James W.'
'Greening, Sarah M.'
'Robertson, Katherine N.'
'Thompson, Alison'
_publ_section_title
;
 A mild synthetic route to α-nitroso diaryl pyrroles.
;
_journal_issue                   30
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6122
_journal_page_last               6128
_journal_paper_doi               10.1039/d4ob00935e
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         '2(C16 H12 N2 O)'
_chemical_formula_sum            'C32 H24 N4 O2'
_chemical_formula_weight         496.55
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-01-08 deposited with the CCDC.	2024-07-08 downloaded from the CCDC.
;
_cell_angle_alpha                90.7407(19)
_cell_angle_beta                 94.8288(17)
_cell_angle_gamma                107.1627(16)
_cell_formula_units_Z            2
_cell_length_a                   9.4686(3)
_cell_length_b                   9.5459(4)
_cell_length_c                   14.1712(5)
_cell_measurement_reflns_used    9813
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      72.3803
_cell_measurement_theta_min      3.1320
_cell_volume                     1218.54(8)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker Instrument Service v8.5.0.11 RC8'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ--geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            48742
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.374
_diffrn_reflns_theta_min         3.132
_diffrn_source_current           1.1
_diffrn_source_power             0.06
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
J. Appl. Cryst. 48, 3-10.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       'prism (cut)'
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.106
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.0027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         4807
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.206
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0681
_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)+(0.0192P)²+1.8955P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1460
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3765
_reflns_number_total             4807
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00935e2.cif
_cod_data_source_block           Compound1A_AT024_EB2
_cod_depositor_comments
'Adding full bibliography for 7160049--7160050.cif.'
_cod_database_code               7160049
_shelx_shelxl_version_number     2019/3
_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_min   0.931
_shelx_estimated_absorpt_t_max   0.986
_diffrn_source_source            'microfocus sealed tube'
loop_
_space_group_symop_operation_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_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 0.3797(2) 0.1491(2) 0.55911(12) 0.0394(5) Uani 1 1 d . . . . .
O2 O 0.6134(2) 0.3930(2) 0.43848(12) 0.0391(4) Uani 1 1 d . . . . .
N1 N 0.5654(2) 0.3958(2) 0.64453(13) 0.0252(4) Uani 1 1 d D . . . .
H1N H 0.582(3) 0.393(3) 0.5825(13) 0.038 Uiso 1 1 d D U . . .
N2 N 0.3593(2) 0.1725(2) 0.64454(14) 0.0306(5) Uani 1 1 d . . . . .
N3 N 0.4554(2) 0.1261(2) 0.36672(14) 0.0285(4) Uani 1 1 d D . . . .
H3N H 0.432(3) 0.146(3) 0.4236(14) 0.043 Uiso 1 1 d D U . . .
N4 N 0.6427(2) 0.3599(2) 0.35679(14) 0.0312(5) Uani 1 1 d . . . . .
C1 C 0.6452(3) 0.5000(2) 0.70993(16) 0.0262(5) Uani 1 1 d . . . . .
C2 C 0.5845(3) 0.4658(3) 0.79704(17) 0.0285(5) Uani 1 1 d . . . . .
H2 H 0.620864 0.519160 0.855534 0.034 Uiso 1 1 calc R U . . .
C3 C 0.4622(3) 0.3405(2) 0.78329(16) 0.0253(5) Uani 1 1 d . . . . .
C4 C 0.4537(3) 0.2961(2) 0.68660(16) 0.0254(5) Uani 1 1 d . . . . .
C5 C 0.7662(3) 0.6270(2) 0.68870(17) 0.0279(5) Uani 1 1 d . . . . .
C6 C 0.8730(3) 0.6985(3) 0.76149(19) 0.0359(6) Uani 1 1 d . . . . .
H6 H 0.866956 0.662519 0.823666 0.043 Uiso 1 1 calc R U . . .
C7 C 0.9876(3) 0.8216(3) 0.7438(2) 0.0410(6) Uani 1 1 d . . . . .
H7 H 1.060881 0.868153 0.793534 0.049 Uiso 1 1 calc R U . . .
C8 C 0.9957(3) 0.8770(3) 0.6536(2) 0.0416(7) Uani 1 1 d . . . . .
H8 H 1.073276 0.962427 0.641885 0.050 Uiso 1 1 calc R U . . .
C9 C 0.8906(3) 0.8075(3) 0.5808(2) 0.0379(6) Uani 1 1 d . . . . .
H9 H 0.895841 0.845455 0.519119 0.045 Uiso 1 1 calc R U . . .
C10 C 0.7769(3) 0.6820(3) 0.59783(17) 0.0309(5) Uani 1 1 d . . . . .
H10 H 0.706250 0.633503 0.547320 0.037 Uiso 1 1 calc R U . . .
C11 C 0.3598(3) 0.2737(2) 0.85372(16) 0.0250(5) Uani 1 1 d . . . . .
C12 C 0.2086(3) 0.2083(3) 0.82679(17) 0.0283(5) Uani 1 1 d . . . . .
H12 H 0.172269 0.201883 0.761823 0.034 Uiso 1 1 calc R U . . .
C13 C 0.1115(3) 0.1528(3) 0.89495(17) 0.0302(5) Uani 1 1 d . . . . .
H13 H 0.009138 0.108270 0.876127 0.036 Uiso 1 1 calc R U . . .
C14 C 0.1627(3) 0.1619(3) 0.99003(17) 0.0298(5) Uani 1 1 d . . . . .
H14 H 0.095590 0.125082 1.036373 0.036 Uiso 1 1 calc R U . . .
C15 C 0.3131(3) 0.2253(3) 1.01703(17) 0.0288(5) Uani 1 1 d . . . . .
H15 H 0.349349 0.230067 1.081934 0.035 Uiso 1 1 calc R U . . .
C16 C 0.4104(3) 0.2817(2) 0.94938(16) 0.0283(5) Uani 1 1 d . . . . .
H16 H 0.512699 0.326166 0.968570 0.034 Uiso 1 1 calc R U . . .
C17 C 0.3911(3) 0.0053(3) 0.30963(16) 0.0266(5) Uani 1 1 d . . . . .
C18 C 0.4591(3) 0.0273(3) 0.22449(16) 0.0277(5) Uani 1 1 d . . . . .
H18 H 0.436368 -0.040717 0.171827 0.033 Uiso 1 1 calc R U . . .
C19 C 0.5647(3) 0.1641(3) 0.22946(16) 0.0261(5) Uani 1 1 d . . . . .
C20 C 0.5605(3) 0.2262(3) 0.32015(16) 0.0273(5) Uani 1 1 d . . . . .
C21 C 0.2742(3) -0.1226(3) 0.33557(17) 0.0275(5) Uani 1 1 d . . . . .
C22 C 0.1886(3) -0.2204(3) 0.26434(18) 0.0329(5) Uani 1 1 d . . . . .
H22 H 0.207806 -0.203385 0.200096 0.040 Uiso 1 1 calc R U . . .
C23 C 0.0756(3) -0.3424(3) 0.28602(19) 0.0362(6) Uani 1 1 d . . . . .
H23 H 0.016829 -0.407267 0.236639 0.043 Uiso 1 1 calc R U . . .
C24 C 0.0483(3) -0.3697(3) 0.3793(2) 0.0388(6) Uani 1 1 d . . . . .
H24 H -0.029426 -0.452835 0.394354 0.047 Uiso 1 1 calc R U . . .
C25 C 0.1350(3) -0.2752(3) 0.45056(19) 0.0372(6) Uani 1 1 d . . . . .
H25 H 0.117940 -0.295147 0.514810 0.045 Uiso 1 1 calc R U . . .
C26 C 0.2465(3) -0.1517(3) 0.42969(18) 0.0338(6) Uani 1 1 d . . . . .
H26 H 0.304192 -0.086755 0.479394 0.041 Uiso 1 1 calc R U . . .
C27 C 0.6582(2) 0.2287(3) 0.15391(16) 0.0257(5) Uani 1 1 d . . . . .
C28 C 0.7179(3) 0.3798(3) 0.14644(17) 0.0282(5) Uani 1 1 d . . . . .
H28 H 0.701570 0.444752 0.192752 0.034 Uiso 1 1 calc R U . . .
C29 C 0.8012(3) 0.4363(3) 0.07175(17) 0.0309(5) Uani 1 1 d . . . . .
H29 H 0.840647 0.539432 0.067174 0.037 Uiso 1 1 calc R U . . .
C30 C 0.8269(3) 0.3428(3) 0.00399(17) 0.0318(5) Uani 1 1 d . . . . .
H30 H 0.883583 0.381742 -0.046976 0.038 Uiso 1 1 calc R U . . .
C31 C 0.7694(3) 0.1921(3) 0.01098(17) 0.0315(5) Uani 1 1 d . . . . .
H31 H 0.787628 0.127621 -0.034871 0.038 Uiso 1 1 calc R U . . .
C32 C 0.6851(3) 0.1357(3) 0.08503(16) 0.0284(5) Uani 1 1 d . . . . .
H32 H 0.645266 0.032402 0.088992 0.034 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
C1 N1 C4 109.43(19) . . ?
C1 N1 H1N 125.4(18) . . ?
C4 N1 H1N 125.2(18) . . ?
O1 N2 C4 114.9(2) . . ?
C17 N3 C20 109.68(19) . . ?
C17 N3 H3N 128(2) . . ?
C20 N3 H3N 122(2) . . ?
O2 N4 C20 115.3(2) . . ?
N1 C1 C2 107.8(2) . . ?
N1 C1 C5 124.1(2) . . ?
C2 C1 C5 128.1(2) . . ?
C3 C2 C1 108.7(2) . . ?
C3 C2 H2 125.6 . . ?
C1 C2 H2 125.6 . . ?
C2 C3 C4 105.7(2) . . ?
C2 C3 C11 126.7(2) . . ?
C4 C3 C11 127.5(2) . . ?
N2 C4 N1 125.8(2) . . ?
N2 C4 C3 125.8(2) . . ?
N1 C4 C3 108.32(19) . . ?
C6 C5 C10 118.8(2) . . ?
C6 C5 C1 119.3(2) . . ?
C10 C5 C1 121.9(2) . . ?
C7 C6 C5 120.6(3) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 120.2(3) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 119.9(2) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.1(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C5 120.5(2) . . ?
C9 C10 H10 119.8 . . ?
C5 C10 H10 119.8 . . ?
C16 C11 C12 118.8(2) . . ?
C16 C11 C3 120.3(2) . . ?
C12 C11 C3 120.7(2) . . ?
C13 C12 C11 120.1(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 120.7(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 119.4(2) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C11 120.8(2) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
N3 C17 C18 107.3(2) . . ?
N3 C17 C21 124.6(2) . . ?
C18 C17 C21 128.1(2) . . ?
C19 C18 C17 109.2(2) . . ?
C19 C18 H18 125.4 . . ?
C17 C18 H18 125.4 . . ?
C18 C19 C20 105.8(2) . . ?
C18 C19 C27 125.8(2) . . ?
C20 C19 C27 128.4(2) . . ?
N4 C20 N3 124.6(2) . . ?
N4 C20 C19 127.4(2) . . ?
N3 C20 C19 108.0(2) . . ?
C22 C21 C26 118.7(2) . . ?
C22 C21 C17 119.1(2) . . ?
C26 C21 C17 122.2(2) . . ?
C23 C22 C21 120.8(2) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C24 C23 C22 120.1(2) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C25 C24 C23 119.4(2) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 121.0(2) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.5 . . ?
C25 C26 C21 120.0(2) . . ?
C25 C26 H26 120.0 . . ?
C21 C26 H26 120.0 . . ?
C28 C27 C32 118.4(2) . . ?
C28 C27 C19 122.5(2) . . ?
C32 C27 C19 119.0(2) . . ?
C29 C28 C27 120.6(2) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C30 C29 C28 120.4(2) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C29 C30 C31 119.7(2) . . ?
C29 C30 H30 120.2 . . ?
C31 C30 H30 120.2 . . ?
C30 C31 C32 120.0(2) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C31 C32 C27 121.0(2) . . ?
C31 C32 H32 119.5 . . ?
C27 C32 H32 119.5 . . ?
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 N2 1.269(3) . ?
O2 N4 1.271(3) . ?
N1 C1 1.354(3) . ?
N1 C4 1.380(3) . ?
N1 H1N 0.906(17) . ?
N2 C4 1.347(3) . ?
N3 C17 1.354(3) . ?
N3 C20 1.381(3) . ?
N3 H3N 0.886(17) . ?
N4 C20 1.354(3) . ?
C1 C2 1.407(3) . ?
C1 C5 1.456(3) . ?
C2 C3 1.396(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.418(3) . ?
C3 C11 1.469(3) . ?
C5 C6 1.397(3) . ?
C5 C10 1.397(3) . ?
C6 C7 1.386(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.390(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.394(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C16 1.393(3) . ?
C11 C12 1.400(3) . ?
C12 C13 1.391(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.391(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.404(3) . ?
C17 C21 1.461(3) . ?
C18 C19 1.388(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.417(3) . ?
C19 C27 1.471(3) . ?
C21 C22 1.392(3) . ?
C21 C26 1.396(3) . ?
C22 C23 1.387(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.381(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.386(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.394(3) . ?
C27 C32 1.400(3) . ?
C28 C29 1.392(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.386(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.388(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.389(3) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
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 H1N O2 0.906(17) 2.088(18) 2.994(3) 177(3) . yes
N3 H3N O1 0.886(17) 2.025(18) 2.899(3) 168(3) . 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
C4 N1 C1 C2 0.7(3) . . . . ?
C4 N1 C1 C5 -176.3(2) . . . . ?
N1 C1 C2 C3 -1.9(3) . . . . ?
C5 C1 C2 C3 175.0(2) . . . . ?
C1 C2 C3 C4 2.3(3) . . . . ?
C1 C2 C3 C11 -175.0(2) . . . . ?
O1 N2 C4 N1 0.8(3) . . . . ?
O1 N2 C4 C3 -174.5(2) . . . . ?
C1 N1 C4 N2 -175.2(2) . . . . ?
C1 N1 C4 C3 0.8(3) . . . . ?
C2 C3 C4 N2 174.0(2) . . . . ?
C11 C3 C4 N2 -8.6(4) . . . . ?
C2 C3 C4 N1 -1.9(3) . . . . ?
C11 C3 C4 N1 175.4(2) . . . . ?
N1 C1 C5 C6 -157.8(2) . . . . ?
C2 C1 C5 C6 25.7(4) . . . . ?
N1 C1 C5 C10 23.8(4) . . . . ?
C2 C1 C5 C10 -152.6(2) . . . . ?
C10 C5 C6 C7 -0.2(4) . . . . ?
C1 C5 C6 C7 -178.6(2) . . . . ?
C5 C6 C7 C8 1.4(4) . . . . ?
C6 C7 C8 C9 -1.2(4) . . . . ?
C7 C8 C9 C10 -0.2(4) . . . . ?
C8 C9 C10 C5 1.3(4) . . . . ?
C6 C5 C10 C9 -1.2(4) . . . . ?
C1 C5 C10 C9 177.2(2) . . . . ?
C2 C3 C11 C16 -31.9(3) . . . . ?
C4 C3 C11 C16 151.3(2) . . . . ?
C2 C3 C11 C12 144.5(2) . . . . ?
C4 C3 C11 C12 -32.3(4) . . . . ?
C16 C11 C12 C13 0.1(3) . . . . ?
C3 C11 C12 C13 -176.4(2) . . . . ?
C11 C12 C13 C14 0.2(4) . . . . ?
C12 C13 C14 C15 -0.9(4) . . . . ?
C13 C14 C15 C16 1.3(3) . . . . ?
C14 C15 C16 C11 -1.0(3) . . . . ?
C12 C11 C16 C15 0.3(3) . . . . ?
C3 C11 C16 C15 176.8(2) . . . . ?
C20 N3 C17 C18 1.2(3) . . . . ?
C20 N3 C17 C21 -179.6(2) . . . . ?
N3 C17 C18 C19 -0.8(3) . . . . ?
C21 C17 C18 C19 180.0(2) . . . . ?
C17 C18 C19 C20 0.1(3) . . . . ?
C17 C18 C19 C27 -179.0(2) . . . . ?
O2 N4 C20 N3 -2.7(3) . . . . ?
O2 N4 C20 C19 176.9(2) . . . . ?
C17 N3 C20 N4 178.6(2) . . . . ?
C17 N3 C20 C19 -1.1(3) . . . . ?
C18 C19 C20 N4 -179.0(2) . . . . ?
C27 C19 C20 N4 0.0(4) . . . . ?
C18 C19 C20 N3 0.6(3) . . . . ?
C27 C19 C20 N3 179.7(2) . . . . ?
N3 C17 C21 C22 162.1(2) . . . . ?
C18 C17 C21 C22 -18.7(4) . . . . ?
N3 C17 C21 C26 -18.9(4) . . . . ?
C18 C17 C21 C26 160.3(2) . . . . ?
C26 C21 C22 C23 1.6(4) . . . . ?
C17 C21 C22 C23 -179.4(2) . . . . ?
C21 C22 C23 C24 -1.1(4) . . . . ?
C22 C23 C24 C25 -0.4(4) . . . . ?
C23 C24 C25 C26 1.5(4) . . . . ?
C24 C25 C26 C21 -1.1(4) . . . . ?
C22 C21 C26 C25 -0.5(4) . . . . ?
C17 C21 C26 C25 -179.5(2) . . . . ?
C18 C19 C27 C28 154.6(2) . . . . ?
C20 C19 C27 C28 -24.3(4) . . . . ?
C18 C19 C27 C32 -23.5(4) . . . . ?
C20 C19 C27 C32 157.6(2) . . . . ?
C32 C27 C28 C29 0.5(3) . . . . ?
C19 C27 C28 C29 -177.6(2) . . . . ?
C27 C28 C29 C30 -0.5(4) . . . . ?
C28 C29 C30 C31 -0.2(4) . . . . ?
C29 C30 C31 C32 0.7(4) . . . . ?
C30 C31 C32 C27 -0.7(4) . . . . ?
C28 C27 C32 C31 0.0(3) . . . . ?
C19 C27 C32 C31 178.2(2) . . . . ?
