#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/44/4024409.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_4024409
loop_
_publ_author_name
'Ying Cheng'
'Bo Wang'
'Xiao-Rong Wang'
'Jian-Hong Zhang'
'De-Cai Fang'
_publ_section_title
;
An Experimental and Theoretical Study on the Interaction of N-Heterocyclic
Carbene-Derived 1,3-Dipoles with Methoxycarbonylallenes: Highly Regio- and
Stereoselective [3+2]-Cycloadditions Controlled by the Structures
of N-Heterocycles of 1,3-Dipoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2357
_journal_page_last               2367
_journal_paper_doi               10.1021/jo802687m
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C35 H32 N4 O2 S'
_chemical_formula_sum            'C35 H32 N4 O2 S'
_chemical_formula_weight         572.71
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.3539(19)
_cell_length_b                   13.481(2)
_cell_length_c                   16.861(2)
_cell_measurement_reflns_used    8456
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.8
_cell_volume                     3035.4(8)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            38456
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  0.9579
_exptl_absorpt_correction_T_min  0.9525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
'Flack H D (1983), 3207 Friedel Pairs, Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         7244
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0366
_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)+(0.0472P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0819
_reflns_number_gt                6788
_reflns_number_total             7244
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802687m_si_008.cif
_cod_data_source_block           shelxl
_cod_database_code               4024409
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.82946(3) 0.42046(3) 0.11641(2) 0.02190(9) Uani 1 1 d . . .
O1 O 0.65342(8) 0.14799(9) 0.21766(8) 0.0368(3) Uani 1 1 d . . .
O2 O 0.78199(8) 0.06328(8) 0.16761(7) 0.0293(3) Uani 1 1 d . . .
N1 N 0.96647(9) 0.17338(9) 0.16946(7) 0.0180(3) Uani 1 1 d . . .
N2 N 1.01311(8) 0.09648(8) 0.12862(7) 0.0181(2) Uani 1 1 d . . .
N3 N 0.89684(9) 0.16475(9) 0.04821(7) 0.0172(2) Uani 1 1 d . . .
N4 N 1.01757(9) 0.35098(9) 0.08278(7) 0.0202(3) Uani 1 1 d . . .
C1 C 0.89361(10) 0.22632(10) 0.12056(8) 0.0165(3) Uani 1 1 d . . .
C2 C 0.97308(10) 0.09491(10) 0.05876(8) 0.0169(3) Uani 1 1 d . . .
C3 C 0.92792(10) 0.33384(10) 0.10222(8) 0.0180(3) Uani 1 1 d . . .
C4 C 0.75063(10) 0.32792(11) 0.15621(8) 0.0185(3) Uani 1 1 d . . .
C5 C 0.78929(10) 0.23555(11) 0.15627(8) 0.0178(3) Uani 1 1 d . . .
C6 C 1.00766(10) 0.20715(10) 0.24076(8) 0.0170(3) Uani 1 1 d . . .
C7 C 0.97905(11) 0.29742(11) 0.27435(8) 0.0216(3) Uani 1 1 d . . .
H7 H 0.9300 0.3372 0.2488 0.026 Uiso 1 1 calc R . .
C8 C 1.02208(12) 0.32954(12) 0.34515(9) 0.0257(3) Uani 1 1 d . . .
H8 H 1.0026 0.3915 0.3672 0.031 Uiso 1 1 calc R . .
C9 C 1.09283(12) 0.27206(12) 0.38360(10) 0.0299(4) Uani 1 1 d . . .
H9 H 1.1223 0.2940 0.4318 0.036 Uiso 1 1 calc R . .
C10 C 1.11999(12) 0.18197(12) 0.35063(9) 0.0289(4) Uani 1 1 d . . .
H10 H 1.1680 0.1418 0.3771 0.035 Uiso 1 1 calc R . .
C11 C 1.07883(11) 0.14885(11) 0.27985(9) 0.0225(3) Uani 1 1 d . . .
H11 H 1.0989 0.0870 0.2581 0.027 Uiso 1 1 calc R . .
C12 C 0.99962(11) 0.01860(10) 0.00037(8) 0.0204(3) Uani 1 1 d . . .
C13 C 1.09651(12) -0.02032(11) 0.00144(9) 0.0262(3) Uani 1 1 d . . .
H13 H 1.1450 0.0062 0.0368 0.031 Uiso 1 1 calc R . .
C14 C 1.12215(13) -0.09735(13) -0.04877(10) 0.0357(4) Uani 1 1 d . . .
H14 H 1.1878 -0.1245 -0.0471 0.043 Uiso 1 1 calc R . .
C15 C 1.05226(15) -0.13497(12) -0.10138(10) 0.0407(5) Uani 1 1 d . . .
H15 H 1.0703 -0.1875 -0.1361 0.049 Uiso 1 1 calc R . .
C16 C 0.95691(15) -0.09672(13) -0.10363(10) 0.0381(4) Uani 1 1 d . . .
H16 H 0.9092 -0.1229 -0.1398 0.046 Uiso 1 1 calc R . .
C17 C 0.93013(13) -0.01970(12) -0.05292(9) 0.0282(4) Uani 1 1 d . . .
H17 H 0.8642 0.0068 -0.0547 0.034 Uiso 1 1 calc R . .
C18 C 0.86935(10) 0.20702(10) -0.02659(8) 0.0167(3) Uani 1 1 d . . .
C19 C 0.94240(11) 0.23948(11) -0.07956(9) 0.0213(3) Uani 1 1 d . . .
H19 H 1.0113 0.2337 -0.0663 0.026 Uiso 1 1 calc R . .
C20 C 0.91446(12) 0.28029(12) -0.15171(9) 0.0268(4) Uani 1 1 d . . .
H20 H 0.9642 0.3013 -0.1883 0.032 Uiso 1 1 calc R . .
C21 C 0.81336(12) 0.29047(12) -0.17050(9) 0.0284(4) Uani 1 1 d . . .
H21 H 0.7942 0.3189 -0.2198 0.034 Uiso 1 1 calc R . .
C22 C 0.74114(11) 0.25928(11) -0.11759(10) 0.0265(3) Uani 1 1 d . . .
H22 H 0.6723 0.2668 -0.1303 0.032 Uiso 1 1 calc R . .
C23 C 0.76883(11) 0.21687(11) -0.04568(9) 0.0222(3) Uani 1 1 d . . .
H23 H 0.7189 0.1947 -0.0097 0.027 Uiso 1 1 calc R . .
C24 C 1.04997(11) 0.45018(11) 0.06941(9) 0.0214(3) Uani 1 1 d . . .
C25 C 1.01581(13) 0.50530(12) 0.00555(10) 0.0337(4) Uani 1 1 d . . .
H25 H 0.9686 0.4775 -0.0303 0.040 Uiso 1 1 calc R . .
C26 C 1.05054(15) 0.60115(13) -0.00602(11) 0.0427(5) Uani 1 1 d . . .
H26 H 1.0269 0.6390 -0.0497 0.051 Uiso 1 1 calc R . .
C27 C 1.11959(13) 0.64192(13) 0.04581(11) 0.0366(4) Uani 1 1 d . . .
H27 H 1.1440 0.7073 0.0374 0.044 Uiso 1 1 calc R . .
C28 C 1.15280(13) 0.58722(13) 0.10963(11) 0.0374(4) Uani 1 1 d . . .
H28 H 1.1991 0.6155 0.1459 0.045 Uiso 1 1 calc R . .
C29 C 1.11893(12) 0.49090(12) 0.12110(11) 0.0328(4) Uani 1 1 d . . .
H29 H 1.1432 0.4530 0.1645 0.039 Uiso 1 1 calc R . .
C30 C 0.65100(10) 0.36415(11) 0.18541(9) 0.0213(3) Uani 1 1 d . . .
H30A H 0.6073 0.3061 0.1949 0.026 Uiso 1 1 calc R . .
H30B H 0.6196 0.4046 0.1432 0.026 Uiso 1 1 calc R . .
C31 C 0.65552(11) 0.42633(13) 0.26180(9) 0.0287(4) Uani 1 1 d . . .
H31 H 0.6961 0.4873 0.2514 0.034 Uiso 1 1 calc R . .
C32 C 0.54891(14) 0.45722(14) 0.28331(11) 0.0382(4) Uani 1 1 d . . .
H32A H 0.5089 0.3980 0.2947 0.057 Uiso 1 1 calc R . .
H32B H 0.5190 0.4934 0.2388 0.057 Uiso 1 1 calc R . .
H32C H 0.5504 0.5001 0.3302 0.057 Uiso 1 1 calc R . .
C33 C 0.70298(14) 0.36920(18) 0.33053(10) 0.0489(6) Uani 1 1 d . . .
H33A H 0.7056 0.4118 0.3776 0.073 Uiso 1 1 calc R . .
H33B H 0.7710 0.3490 0.3159 0.073 Uiso 1 1 calc R . .
H33C H 0.6627 0.3102 0.3422 0.073 Uiso 1 1 calc R . .
C34 C 0.73370(11) 0.14681(11) 0.18383(9) 0.0207(3) Uani 1 1 d . . .
C35 C 0.73030(13) -0.02732(12) 0.18881(12) 0.0356(4) Uani 1 1 d . . .
H35A H 0.7079 -0.0233 0.2441 0.053 Uiso 1 1 calc R . .
H35B H 0.7758 -0.0838 0.1826 0.053 Uiso 1 1 calc R . .
H35C H 0.6721 -0.0362 0.1541 0.053 Uiso 1 1 calc R . .
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'
S S 0.1246 0.1234 '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 S1 C3 91.61(7) . . ?
C34 O2 C35 115.69(12) . . ?
N2 N1 C6 119.46(11) . . ?
N2 N1 C1 112.50(10) . . ?
C6 N1 C1 126.01(11) . . ?
C2 N2 N1 106.12(11) . . ?
C2 N3 C18 124.52(11) . . ?
C2 N3 C1 107.14(11) . . ?
C18 N3 C1 119.78(11) . . ?
C3 N4 C24 120.08(13) . . ?
N1 C1 N3 99.91(10) . . ?
N1 C1 C5 115.20(11) . . ?
N3 C1 C5 113.54(11) . . ?
N1 C1 C3 111.85(11) . . ?
N3 C1 C3 110.61(11) . . ?
C5 C1 C3 105.82(11) . . ?
N2 C2 N3 113.95(12) . . ?
N2 C2 C12 121.49(12) . . ?
N3 C2 C12 124.24(12) . . ?
N4 C3 C1 120.18(12) . . ?
N4 C3 S1 128.10(11) . . ?
C1 C3 S1 111.66(9) . . ?
C5 C4 C30 129.79(13) . . ?
C5 C4 S1 115.14(11) . . ?
C30 C4 S1 115.06(10) . . ?
C4 C5 C34 123.64(13) . . ?
C4 C5 C1 115.18(12) . . ?
C34 C5 C1 121.07(12) . . ?
C7 C6 N1 121.68(13) . . ?
C7 C6 C11 119.01(13) . . ?
N1 C6 C11 119.32(13) . . ?
C8 C7 C6 120.37(14) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C9 C8 C7 120.60(15) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 118.84(15) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C9 C10 C11 121.60(15) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C10 C11 C6 119.59(14) . . ?
C10 C11 H11 120.2 . . ?
C6 C11 H11 120.2 . . ?
C17 C12 C13 119.14(14) . . ?
C17 C12 C2 122.17(13) . . ?
C13 C12 C2 118.60(13) . . ?
C14 C13 C12 120.25(16) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.04(16) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 120.34(16) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 120.07(17) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C16 120.15(16) . . ?
C12 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C23 C18 C19 119.92(13) . . ?
C23 C18 N3 119.39(12) . . ?
C19 C18 N3 120.68(12) . . ?
C20 C19 C18 119.93(14) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 119.96(14) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 120.02(14) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 120.22(14) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C18 C23 C22 119.95(14) . . ?
C18 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C29 C24 C25 119.77(14) . . ?
C29 C24 N4 118.42(14) . . ?
C25 C24 N4 121.80(14) . . ?
C24 C25 C26 119.93(16) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C27 C26 C25 120.26(17) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C28 C27 C26 119.67(16) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C27 C28 C29 120.29(17) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
C24 C29 C28 120.05(16) . . ?
C24 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C4 C30 C31 114.67(12) . . ?
C4 C30 H30A 108.6 . . ?
C31 C30 H30A 108.6 . . ?
C4 C30 H30B 108.6 . . ?
C31 C30 H30B 108.6 . . ?
H30A C30 H30B 107.6 . . ?
C32 C31 C33 110.11(14) . . ?
C32 C31 C30 108.12(13) . . ?
C33 C31 C30 112.11(14) . . ?
C32 C31 H31 108.8 . . ?
C33 C31 H31 108.8 . . ?
C30 C31 H31 108.8 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
O1 C34 O2 122.50(14) . . ?
O1 C34 C5 125.35(14) . . ?
O2 C34 C5 112.15(12) . . ?
O2 C35 H35A 109.5 . . ?
O2 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
O2 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 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
S1 C4 1.7649(15) . ?
S1 C3 1.7747(14) . ?
O1 C34 1.2145(17) . ?
O2 C34 1.3263(17) . ?
O2 C35 1.4477(18) . ?
N1 N2 1.3918(15) . ?
N1 C6 1.3983(18) . ?
N1 C1 1.4614(17) . ?
N2 C2 1.2937(18) . ?
N3 C2 1.3981(17) . ?
N3 C18 1.4318(18) . ?
N3 C1 1.4761(18) . ?
N4 C3 1.2626(17) . ?
N4 C24 1.4235(18) . ?
C1 C5 1.5228(19) . ?
C1 C3 1.551(2) . ?
C2 C12 1.4674(19) . ?
C4 C5 1.348(2) . ?
C4 C30 1.5003(19) . ?
C5 C34 1.483(2) . ?
C6 C7 1.396(2) . ?
C6 C11 1.398(2) . ?
C7 C8 1.394(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.383(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C17 1.391(2) . ?
C12 C13 1.396(2) . ?
C13 C14 1.383(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.374(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.392(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C23 1.387(2) . ?
C18 C19 1.393(2) . ?
C19 C20 1.386(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.394(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.379(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.391(2) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C29 1.382(2) . ?
C24 C25 1.386(2) . ?
C25 C26 1.387(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.384(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.378(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.389(2) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 C31 1.538(2) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.527(2) . ?
C31 C33 1.529(3) . ?
C31 H31 1.0000 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
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
C6 N1 N2 C2 -166.73(12) . . . . ?
C1 N1 N2 C2 -1.97(15) . . . . ?
N2 N1 C1 N3 4.96(14) . . . . ?
C6 N1 C1 N3 168.53(12) . . . . ?
N2 N1 C1 C5 127.00(12) . . . . ?
C6 N1 C1 C5 -69.44(17) . . . . ?
N2 N1 C1 C3 -112.11(12) . . . . ?
C6 N1 C1 C3 51.45(17) . . . . ?
C2 N3 C1 N1 -5.95(13) . . . . ?
C18 N3 C1 N1 -155.25(11) . . . . ?
C2 N3 C1 C5 -129.16(12) . . . . ?
C18 N3 C1 C5 81.54(15) . . . . ?
C2 N3 C1 C3 112.05(12) . . . . ?
C18 N3 C1 C3 -37.26(16) . . . . ?
N1 N2 C2 N3 -2.33(15) . . . . ?
N1 N2 C2 C12 -176.10(12) . . . . ?
C18 N3 C2 N2 153.09(13) . . . . ?
C1 N3 C2 N2 5.62(15) . . . . ?
C18 N3 C2 C12 -33.3(2) . . . . ?
C1 N3 C2 C12 179.19(13) . . . . ?
C24 N4 C3 C1 -177.21(12) . . . . ?
C24 N4 C3 S1 0.0(2) . . . . ?
N1 C1 C3 N4 43.44(17) . . . . ?
N3 C1 C3 N4 -66.99(16) . . . . ?
C5 C1 C3 N4 169.63(12) . . . . ?
N1 C1 C3 S1 -134.18(10) . . . . ?
N3 C1 C3 S1 115.40(10) . . . . ?
C5 C1 C3 S1 -7.98(13) . . . . ?
C4 S1 C3 N4 -170.73(13) . . . . ?
C4 S1 C3 C1 6.65(10) . . . . ?
C3 S1 C4 C5 -3.36(12) . . . . ?
C3 S1 C4 C30 176.21(11) . . . . ?
C30 C4 C5 C34 3.2(2) . . . . ?
S1 C4 C5 C34 -177.26(11) . . . . ?
C30 C4 C5 C1 179.39(13) . . . . ?
S1 C4 C5 C1 -1.12(16) . . . . ?
N1 C1 C5 C4 129.91(13) . . . . ?
N3 C1 C5 C4 -115.72(14) . . . . ?
C3 C1 C5 C4 5.79(16) . . . . ?
N1 C1 C5 C34 -53.84(17) . . . . ?
N3 C1 C5 C34 60.53(16) . . . . ?
C3 C1 C5 C34 -177.96(12) . . . . ?
N2 N1 C6 C7 164.66(12) . . . . ?
C1 N1 C6 C7 2.1(2) . . . . ?
N2 N1 C6 C11 -15.80(19) . . . . ?
C1 N1 C6 C11 -178.33(13) . . . . ?
N1 C6 C7 C8 -179.44(13) . . . . ?
C11 C6 C7 C8 1.0(2) . . . . ?
C6 C7 C8 C9 -0.7(2) . . . . ?
C7 C8 C9 C10 -0.1(2) . . . . ?
C8 C9 C10 C11 0.7(2) . . . . ?
C9 C10 C11 C6 -0.4(2) . . . . ?
C7 C6 C11 C10 -0.5(2) . . . . ?
N1 C6 C11 C10 180.00(13) . . . . ?
N2 C2 C12 C17 145.06(14) . . . . ?
N3 C2 C12 C17 -28.0(2) . . . . ?
N2 C2 C12 C13 -31.5(2) . . . . ?
N3 C2 C12 C13 155.44(13) . . . . ?
C17 C12 C13 C14 -1.3(2) . . . . ?
C2 C12 C13 C14 175.28(14) . . . . ?
C12 C13 C14 C15 1.2(2) . . . . ?
C13 C14 C15 C16 -0.6(3) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C13 C12 C17 C16 0.8(2) . . . . ?
C2 C12 C17 C16 -175.65(14) . . . . ?
C15 C16 C17 C12 -0.2(2) . . . . ?
C2 N3 C18 C23 136.51(14) . . . . ?
C1 N3 C18 C23 -79.79(17) . . . . ?
C2 N3 C18 C19 -44.4(2) . . . . ?
C1 N3 C18 C19 99.26(15) . . . . ?
C23 C18 C19 C20 -0.9(2) . . . . ?
N3 C18 C19 C20 -179.95(13) . . . . ?
C18 C19 C20 C21 1.2(2) . . . . ?
C19 C20 C21 C22 -0.5(2) . . . . ?
C20 C21 C22 C23 -0.5(2) . . . . ?
C19 C18 C23 C22 -0.1(2) . . . . ?
N3 C18 C23 C22 178.95(13) . . . . ?
C21 C22 C23 C18 0.8(2) . . . . ?
C3 N4 C24 C29 113.42(16) . . . . ?
C3 N4 C24 C25 -67.9(2) . . . . ?
C29 C24 C25 C26 -0.3(3) . . . . ?
N4 C24 C25 C26 -178.94(15) . . . . ?
C24 C25 C26 C27 0.3(3) . . . . ?
C25 C26 C27 C28 -0.8(3) . . . . ?
C26 C27 C28 C29 1.4(3) . . . . ?
C25 C24 C29 C28 0.9(3) . . . . ?
N4 C24 C29 C28 179.56(15) . . . . ?
C27 C28 C29 C24 -1.4(3) . . . . ?
C5 C4 C30 C31 108.43(18) . . . . ?
S1 C4 C30 C31 -71.07(15) . . . . ?
C4 C30 C31 C32 179.95(14) . . . . ?
C4 C30 C31 C33 -58.49(18) . . . . ?
C35 O2 C34 O1 3.4(2) . . . . ?
C35 O2 C34 C5 -176.86(13) . . . . ?
C4 C5 C34 O1 -9.2(2) . . . . ?
C1 C5 C34 O1 174.84(14) . . . . ?
C4 C5 C34 O2 170.98(14) . . . . ?
C1 C5 C34 O2 -4.95(18) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658915
