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#$Date: 2023-06-05 06:58:41 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284217 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/88/1568898.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_1568898
loop_
_publ_author_name
'Rahman, Md Mahbubur'
'Meng, Guangrong'
'Bisz, Elwira'
'Dziuk, Błażej'
'Lalancette, Roger'
'Szostak, Roman'
'Szostak, Michal'
_publ_section_title
;
 ItOct (ItOctyl) - pushing the limits of ItBu: highly
 hindered electron-rich N-aliphatic N-heterocyclic carbenes.
;
_journal_issue                   19
_journal_name_full               'Chemical science'
_journal_page_first              5141
_journal_page_last               5147
_journal_paper_doi               10.1039/d3sc01006f
_journal_volume                  14
_journal_year                    2023
_chemical_formula_sum            'C19 H36 Cl Cu N2'
_chemical_formula_weight         391.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2023-02-01 deposited with the CCDC.	2023-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.351(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6916(6)
_cell_length_b                   13.5030(7)
_cell_length_c                   13.0909(6)
_cell_measurement_reflns_used    14984
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.994
_cell_measurement_theta_min      2.616
_cell_volume                     2233.67(19)
_computing_cell_refinement       'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_data_collection       'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean '1024 x 1024 with blocks 2 x 2'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  Xcalibur
_diffrn_measurement_method       ω--scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_av_unetI/netI     0.1108
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14984
_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         25.994
_diffrn_reflns_theta_min         2.616
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97394
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.824
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.824
_refine_ls_R_factor_all          0.1333
_refine_ls_R_factor_gt           0.0458
_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)+(0.0465P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.1057
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1951
_reflns_number_total             4387
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc01006f2.cif
_cod_data_source_block           BD315_a
_cod_depositor_comments
'Adding full bibliography for 1568897--1568901.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1568898
_shelx_shelxl_version_number     2014/7
_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.
;
_exptl_absorpt_special_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.57 (release 26-01-2010 CrysAlis171 .NET)
(compiled Jan 26 2010,14:36:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Cu1 Cu 0.15783(4) 0.35706(3) 0.37921(3) 0.0609(2) Uani 1 1 d . . . . .
C1 C 0.2563(3) 0.3217(3) 0.4900(3) 0.0495(9) Uani 1 1 d . . . . .
Cl1 Cl 0.04929(9) 0.39677(9) 0.25676(8) 0.0897(4) Uani 1 1 d . . . . .
N1 N 0.3334(2) 0.2527(2) 0.4900(2) 0.0542(8) Uani 1 1 d . . . . .
N2 N 0.2632(2) 0.3575(2) 0.5871(2) 0.0531(8) Uani 1 1 d . . . . .
C2 C 0.3885(3) 0.2480(3) 0.5851(3) 0.0700(12) Uani 1 1 d . . . . .
H2 H 0.4463 0.2075 0.6042 0.084 Uiso 1 1 calc R U . . .
C4 C 0.3560(3) 0.1925(3) 0.3992(3) 0.0614(11) Uani 1 1 d . . . . .
C3 C 0.3443(3) 0.3117(3) 0.6445(3) 0.0689(12) Uani 1 1 d . . . . .
H3 H 0.3648 0.3234 0.7135 0.083 Uiso 1 1 calc R U . . .
C5 C 0.2570(3) 0.1327(3) 0.3576(3) 0.0664(11) Uani 1 1 d . . . . .
H5A H 0.2051 0.1814 0.3316 0.080 Uiso 1 1 calc R U . . .
H5B H 0.2774 0.0970 0.2982 0.080 Uiso 1 1 calc R U . . .
C8 C 0.3830(3) 0.2635(3) 0.3143(3) 0.0830(13) Uani 1 1 d . . . . .
H8A H 0.4047 0.2262 0.2575 0.125 Uiso 1 1 calc R U . . .
H8B H 0.4395 0.3066 0.3402 0.125 Uiso 1 1 calc R U . . .
H8C H 0.3218 0.3023 0.2920 0.125 Uiso 1 1 calc R U . . .
C7 C 0.4521(3) 0.1261(3) 0.4280(4) 0.1010(16) Uani 1 1 d . . . . .
H7A H 0.4650 0.0853 0.3704 0.151 Uiso 1 1 calc R U . . .
H7B H 0.4385 0.0849 0.4850 0.151 Uiso 1 1 calc R U . . .
H7C H 0.5131 0.1666 0.4465 0.151 Uiso 1 1 calc R U . . .
C6 C 0.1970(4) 0.0582(3) 0.4185(4) 0.0832(14) Uani 1 1 d . . . . .
C9 C 0.1487(4) 0.1034(4) 0.5093(4) 0.1165(19) Uani 1 1 d . . . . .
H9A H 0.1005 0.1551 0.4858 0.175 Uiso 1 1 calc R U . . .
H9B H 0.2038 0.1305 0.5564 0.175 Uiso 1 1 calc R U . . .
H9C H 0.1113 0.0533 0.5433 0.175 Uiso 1 1 calc R U . . .
C10 C 0.1078(5) 0.0198(5) 0.3436(4) 0.179(3) Uani 1 1 d . . . . .
H10A H 0.0599 0.0729 0.3240 0.268 Uiso 1 1 calc R U . . .
H10B H 0.0706 -0.0319 0.3756 0.268 Uiso 1 1 calc R U . . .
H10C H 0.1366 -0.0060 0.2837 0.268 Uiso 1 1 calc R U . . .
C11 C 0.2668(5) -0.0291(4) 0.4592(5) 0.179(3) Uani 1 1 d . . . . .
H11A H 0.2967 -0.0610 0.4031 0.268 Uiso 1 1 calc R U . . .
H11B H 0.2245 -0.0758 0.4927 0.268 Uiso 1 1 calc R U . . .
H11C H 0.3226 -0.0050 0.5074 0.268 Uiso 1 1 calc R U . . .
C12 C 0.1873(3) 0.4295(3) 0.6250(3) 0.0588(11) Uani 1 1 d . . . . .
C13 C 0.1785(3) 0.5236(3) 0.5596(3) 0.0571(10) Uani 1 1 d . . . . .
H13A H 0.1202 0.5613 0.5828 0.068 Uiso 1 1 calc R U . . .
H13B H 0.1559 0.5024 0.4902 0.068 Uiso 1 1 calc R U . . .
C14 C 0.2689(3) 0.5979(3) 0.5505(3) 0.0716(12) Uani 1 1 d . . . . .
C15 C 0.2198(3) 0.4524(3) 0.7391(3) 0.0920(15) Uani 1 1 d . . . . .
H15A H 0.2920 0.4744 0.7470 0.138 Uiso 1 1 calc R U . . .
H15B H 0.2128 0.3936 0.7792 0.138 Uiso 1 1 calc R U . . .
H15C H 0.1748 0.5033 0.7621 0.138 Uiso 1 1 calc R U . . .
C16 C 0.0789(3) 0.3796(3) 0.6180(3) 0.0797(13) Uani 1 1 d . . . . .
H16A H 0.0554 0.3672 0.5473 0.120 Uiso 1 1 calc R U . . .
H16B H 0.0293 0.4222 0.6474 0.120 Uiso 1 1 calc R U . . .
H16C H 0.0841 0.3181 0.6549 0.120 Uiso 1 1 calc R U . . .
C17 C 0.3702(3) 0.5505(3) 0.5240(4) 0.1159(19) Uani 1 1 d . . . . .
H17A H 0.3568 0.5125 0.4622 0.174 Uiso 1 1 calc R U . . .
H17B H 0.3969 0.5077 0.5790 0.174 Uiso 1 1 calc R U . . .
H17C H 0.4215 0.6010 0.5140 0.174 Uiso 1 1 calc R U . . .
C18 C 0.2912(4) 0.6610(4) 0.6469(4) 0.149(3) Uani 1 1 d . . . . .
H18A H 0.3308 0.7186 0.6309 0.224 Uiso 1 1 calc R U . . .
H18B H 0.3313 0.6230 0.6989 0.224 Uiso 1 1 calc R U . . .
H18C H 0.2255 0.6810 0.6714 0.224 Uiso 1 1 calc R U . . .
C19 C 0.2321(4) 0.6680(4) 0.4633(5) 0.137(2) Uani 1 1 d . . . . .
H19A H 0.2851 0.7177 0.4566 0.206 Uiso 1 1 calc R U . . .
H19B H 0.1672 0.6993 0.4779 0.206 Uiso 1 1 calc R U . . .
H19C H 0.2206 0.6314 0.4004 0.206 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 0.0033 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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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 Cu1 Cl1 179.76(12) . . ?
N1 C1 N2 105.2(3) . . ?
N1 C1 Cu1 127.1(3) . . ?
N2 C1 Cu1 127.7(3) . . ?
C1 N1 C2 109.9(3) . . ?
C1 N1 C4 124.7(3) . . ?
C2 N1 C4 125.4(3) . . ?
C1 N2 C3 109.5(3) . . ?
C1 N2 C12 124.0(3) . . ?
C3 N2 C12 126.3(3) . . ?
C3 C2 N1 107.2(3) . . ?
C3 C2 H2 126.4 . . ?
N1 C2 H2 126.4 . . ?
N1 C4 C8 108.1(3) . . ?
N1 C4 C7 109.3(3) . . ?
C8 C4 C7 108.6(3) . . ?
N1 C4 C5 110.8(3) . . ?
C8 C4 C5 107.4(3) . . ?
C7 C4 C5 112.5(3) . . ?
C2 C3 N2 108.2(3) . . ?
C2 C3 H3 125.9 . . ?
N2 C3 H3 125.9 . . ?
C6 C5 C4 125.9(3) . . ?
C6 C5 H5A 105.8 . . ?
C4 C5 H5A 105.8 . . ?
C6 C5 H5B 105.8 . . ?
C4 C5 H5B 105.8 . . ?
H5A C5 H5B 106.2 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C6 C10 108.2(4) . . ?
C9 C6 C5 113.6(4) . . ?
C10 C6 C5 105.4(4) . . ?
C9 C6 C11 107.3(4) . . ?
C10 C6 C11 109.4(5) . . ?
C5 C6 C11 112.7(4) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C16 107.5(3) . . ?
N2 C12 C13 111.8(3) . . ?
C16 C12 C13 108.3(3) . . ?
N2 C12 C15 109.3(3) . . ?
C16 C12 C15 107.7(3) . . ?
C13 C12 C15 112.0(3) . . ?
C12 C13 C14 124.7(3) . . ?
C12 C13 H13A 106.2 . . ?
C14 C13 H13A 106.2 . . ?
C12 C13 H13B 106.2 . . ?
C14 C13 H13B 106.2 . . ?
H13A C13 H13B 106.4 . . ?
C17 C14 C19 107.5(4) . . ?
C17 C14 C18 109.4(4) . . ?
C19 C14 C18 107.0(4) . . ?
C17 C14 C13 113.5(4) . . ?
C19 C14 C13 106.5(4) . . ?
C18 C14 C13 112.5(4) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
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
Cu1 C1 1.885(3) . ?
Cu1 Cl1 2.0839(10) . ?
C1 N1 1.351(4) . ?
C1 N2 1.356(4) . ?
N1 C2 1.371(4) . ?
N1 C4 1.490(4) . ?
N2 C3 1.365(4) . ?
N2 C12 1.485(4) . ?
C2 C3 1.319(5) . ?
C2 H2 0.9300 . ?
C4 C8 1.530(5) . ?
C4 C7 1.532(5) . ?
C4 C5 1.549(5) . ?
C3 H3 0.9300 . ?
C5 C6 1.530(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C6 C9 1.516(5) . ?
C6 C10 1.518(6) . ?
C6 C11 1.539(7) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C16 1.526(5) . ?
C12 C13 1.532(5) . ?
C12 C15 1.544(4) . ?
C13 C14 1.537(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C17 1.505(5) . ?
C14 C19 1.523(6) . ?
C14 C18 1.526(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
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
C2 H2 Cl1 0.93 2.68 3.490(4) 145.7 4_666
C16 H16B Cl1 0.96 2.96 3.867(4) 157.5 3_566
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
N2 C1 N1 C2 -1.4(4) . . . . ?
Cu1 C1 N1 C2 -179.7(3) . . . . ?
N2 C1 N1 C4 179.7(3) . . . . ?
Cu1 C1 N1 C4 1.4(5) . . . . ?
N1 C1 N2 C3 0.8(4) . . . . ?
Cu1 C1 N2 C3 179.1(3) . . . . ?
N1 C1 N2 C12 -174.6(3) . . . . ?
Cu1 C1 N2 C12 3.7(5) . . . . ?
C1 N1 C2 C3 1.6(5) . . . . ?
C4 N1 C2 C3 -179.6(3) . . . . ?
C1 N1 C4 C8 59.4(4) . . . . ?
C2 N1 C4 C8 -119.3(4) . . . . ?
C1 N1 C4 C7 177.4(4) . . . . ?
C2 N1 C4 C7 -1.3(5) . . . . ?
C1 N1 C4 C5 -58.0(5) . . . . ?
C2 N1 C4 C5 123.2(4) . . . . ?
N1 C2 C3 N2 -1.0(5) . . . . ?
C1 N2 C3 C2 0.1(5) . . . . ?
C12 N2 C3 C2 175.4(4) . . . . ?
N1 C4 C5 C6 -57.5(5) . . . . ?
C8 C4 C5 C6 -175.4(4) . . . . ?
C7 C4 C5 C6 65.2(5) . . . . ?
C4 C5 C6 C9 62.1(6) . . . . ?
C4 C5 C6 C10 -179.6(4) . . . . ?
C4 C5 C6 C11 -60.3(6) . . . . ?
C1 N2 C12 C16 62.9(4) . . . . ?
C3 N2 C12 C16 -111.7(4) . . . . ?
C1 N2 C12 C13 -55.9(4) . . . . ?
C3 N2 C12 C13 129.5(4) . . . . ?
C1 N2 C12 C15 179.5(3) . . . . ?
C3 N2 C12 C15 4.9(5) . . . . ?
N2 C12 C13 C14 -65.0(4) . . . . ?
C16 C12 C13 C14 176.7(3) . . . . ?
C15 C12 C13 C14 58.1(5) . . . . ?
C12 C13 C14 C17 51.3(5) . . . . ?
C12 C13 C14 C19 169.5(4) . . . . ?
C12 C13 C14 C18 -73.6(5) . . . . ?
