#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/90/2209068.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2209068
loop_
_publ_author_name
'Seferoğlu, Zeynel'
'Hökelek, Tuncer'
'Şahin, Ertan'
'Ertan, Nermin'
_publ_section_title
;
 3-(4-Chlorophenyldiazenyl)-1-methyl-2-phenyl-1H-indole
;
_journal_coeditor_code           AT2026
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2108
_journal_page_last               o2110
_journal_paper_doi               10.1107/S1600536806012542
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C21 H16 Cl N3'
_chemical_formula_moiety         'C21 H16 Cl N3'
_chemical_formula_sum            'C21 H16 Cl N3'
_chemical_formula_weight         345.82
_chemical_name_systematic
;
3-(4-Chlorophenyldiazenyl)-1-methyl-2-phenyl-1H-indole
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2bc 2ac'
_symmetry_space_group_name_H-M   'P c a b'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   8.0836(10)
_cell_length_b                   27.952(4)
_cell_length_c                   30.483(3)
_cell_measurement_reflns_used    7332
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.594
_cell_measurement_theta_min      2.5624
_cell_volume                     6887.7(15)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID-S'
_diffrn_measurement_method       oscillation
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0958
_diffrn_reflns_av_sigmaI/netI    0.0684
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            64891
_diffrn_reflns_theta_full        30.57
_diffrn_reflns_theta_max         30.57
_diffrn_reflns_theta_min         2.56
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  0.9774
_exptl_absorpt_correction_T_min  0.9240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod-shaped
_exptl_crystal_F_000             2880
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.271
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     555
_refine_ls_number_reflns         10527
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.177
_refine_ls_R_factor_all          0.1691
_refine_ls_R_factor_gt           0.1078
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0393P)²+4.4415P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1817
_refine_ls_wR_factor_ref         0.2054
_reflns_number_gt                6382
_reflns_number_total             10527
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2026.cif
_cod_data_source_block           I
_cod_database_code               2209068
_cod_database_fobs_code          2209068
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'x+1/2, -y, -z+1/2'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'-x-1/2, y, z-1/2'
'x-1/2, -y-1/2, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Cl Cl1 0.53752(14) 0.34057(3) 0.05653(4) 0.0753(3) Uani d . 1
N N1 0.8228(3) 0.00356(8) -0.03756(9) 0.0457(6) Uani d . 1
N N2 0.6847(3) 0.11924(8) -0.00584(8) 0.0460(6) Uani d . 1
N N3 0.6155(3) 0.13222(9) 0.02988(9) 0.0504(6) Uani d . 1
C C1 0.7469(4) -0.00917(11) 0.00167(11) 0.0476(7) Uani d . 1
C C2 0.7384(5) -0.05417(12) 0.02136(13) 0.0573(9) Uani d . 1
C C3 0.6592(5) -0.05689(14) 0.06117(14) 0.0658(10) Uani d . 1
C C4 0.5863(5) -0.01703(15) 0.08010(13) 0.0626(10) Uani d . 1
C C5 0.5922(4) 0.02752(13) 0.06069(11) 0.0518(8) Uani d . 1
C C6 0.6773(4) 0.03195(10) 0.02080(10) 0.0448(7) Uani d . 1
C C7 0.7168(4) 0.07066(10) -0.00856(10) 0.0424(7) Uani d . 1
C C8 0.8047(4) 0.05199(10) -0.04387(10) 0.0439(7) Uani d . 1
C C9 0.8684(4) 0.07692(11) -0.08285(10) 0.0456(7) Uani d . 1
C C10 0.9463(4) 0.12140(12) -0.07811(13) 0.0549(8) Uani d . 1
C C11 1.0055(5) 0.14513(15) -0.11431(15) 0.0708(11) Uani d . 1
C C12 0.9900(6) 0.12555(17) -0.15548(17) 0.0810(13) Uani d . 1
C C13 0.9143(6) 0.08209(17) -0.16038(15) 0.0781(12) Uani d . 1
C C14 0.8525(5) 0.05785(13) -0.12453(12) 0.0585(9) Uani d . 1
C C15 0.9194(5) -0.03009(11) -0.06385(12) 0.0597(9) Uani d . 1
C C16 0.5960(4) 0.18267(11) 0.03304(10) 0.0473(7) Uani d . 1
C C17 0.5175(5) 0.19923(12) 0.07049(12) 0.0571(9) Uani d . 1
C C18 0.4978(5) 0.24788(13) 0.07786(12) 0.0585(9) Uani d . 1
C C19 0.5582(4) 0.27960(11) 0.04745(11) 0.0529(8) Uani d . 1
C C20 0.6373(5) 0.26400(12) 0.00998(12) 0.0569(9) Uani d . 1
C C21 0.6569(5) 0.21560(12) 0.00295(11) 0.0542(8) Uani d . 1
H H2 0.790(4) -0.0801(10) 0.0073(10) 0.045(8) Uiso d . 1
H H3 0.649(5) -0.0869(14) 0.0756(13) 0.081(12) Uiso d . 1
H H4 0.529(5) -0.0180(12) 0.1052(12) 0.068(12) Uiso d . 1
H H5 0.543(4) 0.0561(12) 0.0745(11) 0.059(10) Uiso d . 1
H H10 0.960(4) 0.1336(11) -0.0495(11) 0.055(10) Uiso d . 1
H H11 1.059(5) 0.1769(15) -0.1121(13) 0.088(13) Uiso d . 1
H H12 1.040(5) 0.1434(16) -0.1806(15) 0.104(15) Uiso d . 1
H H13 0.900(5) 0.0681(14) -0.1885(14) 0.086(14) Uiso d . 1
H H14 0.801(4) 0.0289(11) -0.1276(10) 0.054(10) Uiso d . 1
H H15A 0.9092 -0.0616 -0.0517 0.090 Uiso calc R 1
H H15B 1.0336 -0.0206 -0.0637 0.090 Uiso calc R 1
H H15C 0.8789 -0.0301 -0.0935 0.090 Uiso calc R 1
H H17 0.483(4) 0.1755(12) 0.0915(12) 0.065(10) Uiso d . 1
H H18 0.444(5) 0.2578(13) 0.1043(12) 0.073(11) Uiso d . 1
H H20 0.683(5) 0.2888(13) -0.0094(12) 0.075(11) Uiso d . 1
H H21 0.707(4) 0.2034(12) -0.0228(11) 0.066(11) Uiso d . 1
Cl Cl1' 0.64881(15) -0.04734(3) -0.18667(4) 0.0879(4) Uani d . 1
N N1' 0.5139(3) -0.39505(9) -0.27022(9) 0.0511(7) Uani d . 1
N N2' 0.5869(3) -0.27488(9) -0.23757(8) 0.0472(6) Uani d . 1
N N3' 0.6404(3) -0.25842(9) -0.20137(9) 0.0507(6) Uani d . 1
C C1' 0.5788(4) -0.40452(11) -0.22871(11) 0.0528(8) Uani d . 1
C C2' 0.6031(5) -0.44834(13) -0.20820(14) 0.0653(10) Uani d . 1
C C3' 0.6675(5) -0.44766(16) -0.16640(14) 0.0741(12) Uani d . 1
C C4' 0.7066(5) -0.40496(16) -0.14559(14) 0.0719(11) Uani d . 1
C C5' 0.6843(5) -0.36184(14) -0.16613(12) 0.0609(9) Uani d . 1
C C6' 0.6189(4) -0.36101(11) -0.20842(10) 0.0491(7) Uani d . 1
C C7' 0.5757(4) -0.32428(11) -0.23947(10) 0.0468(7) Uani d . 1
C C8' 0.5123(4) -0.34649(10) -0.27674(10) 0.0458(7) Uani d . 1
C C9' 0.4609(4) -0.32430(10) -0.31831(10) 0.0447(7) Uani d . 1
C C10' 0.3596(4) -0.28421(12) -0.31830(12) 0.0522(8) Uani d . 1
C C11' 0.3218(5) -0.26138(14) -0.35717(14) 0.0663(10) Uani d . 1
C C12' 0.3827(6) -0.27861(14) -0.39624(14) 0.0703(12) Uani d . 1
C C13' 0.4798(5) -0.31888(14) -0.39711(12) 0.0620(10) Uani d . 1
C C14' 0.5191(4) -0.34177(12) -0.35835(11) 0.0518(8) Uani d . 1
C C15' 0.4314(5) -0.43090(12) -0.29704(13) 0.0713(11) Uani d . 1
C C16' 0.6409(4) -0.20735(11) -0.20031(10) 0.0465(7) Uani d . 1
C C17' 0.7387(5) -0.18588(13) -0.16900(12) 0.0568(9) Uani d . 1
C C18' 0.7441(5) -0.13657(13) -0.16497(13) 0.0601(9) Uani d . 1
C C19' 0.6469(4) -0.10930(11) -0.19184(12) 0.0555(8) Uani d . 1
C C20' 0.5462(5) -0.13012(13) -0.22257(13) 0.0618(9) Uani d . 1
C C21' 0.5426(5) -0.17913(12) -0.22727(12) 0.0583(9) Uani d . 1
H H2' 0.582(4) -0.4757(12) -0.2218(11) 0.062(11) Uiso d . 1
H H3' 0.682(5) -0.4772(13) -0.1515(12) 0.074(11) Uiso d . 1
H H4' 0.750(4) -0.4065(11) -0.1167(11) 0.056(9) Uiso d . 1
H H5' 0.714(4) -0.3323(12) -0.1524(11) 0.068(11) Uiso d . 1
H H10' 0.315(4) -0.2731(11) -0.2916(11) 0.063(11) Uiso d . 1
H H11' 0.257(5) -0.2344(14) -0.3561(13) 0.088(14) Uiso d . 1
H H12' 0.363(4) -0.2639(12) -0.4216(12) 0.064(11) Uiso d . 1
H H13' 0.521(5) -0.3314(14) -0.4237(14) 0.090(14) Uiso d . 1
H H14' 0.594(5) -0.3681(13) -0.3581(12) 0.075(12) Uiso d . 1
H H15D 0.4531 -0.4621 -0.2853 0.107 Uiso calc R 1
H H15E 0.4724 -0.4291 -0.3266 0.107 Uiso calc R 1
H H15F 0.3144 -0.4251 -0.2970 0.107 Uiso calc R 1
H H17' 0.800(4) -0.2058(11) -0.1521(11) 0.057(10) Uiso d . 1
H H18' 0.812(4) -0.1220(12) -0.1438(11) 0.065(10) Uiso d . 1
H H20' 0.480(4) -0.1111(12) -0.2390(11) 0.062(10) Uiso d . 1
H H21' 0.466(4) -0.1943(13) -0.2464(12) 0.071(11) Uiso d . 1
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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C8 N1 C1 109.0(3) yes
C8 N1 C15 127.9(3) yes
C1 N1 C15 122.9(3) yes
N3 N2 C7 114.3(3) yes
N2 N3 C16 112.8(3) yes
N1 C1 C2 128.5(3) ?
N1 C1 C6 108.9(3) ?
C2 C1 C6 122.6(3) ?
C3 C2 C1 116.9(4) ?
C3 C2 H2 124.5(19) ?
C1 C2 H2 118.6(19) ?
C2 C3 C4 121.4(4) ?
C2 C3 H3 120(2) ?
C4 C3 H3 119(2) ?
C5 C4 C3 122.2(4) ?
C5 C4 H4 114(2) ?
C3 C4 H4 124(2) ?
C4 C5 C6 117.9(4) ?
C4 C5 H5 122.3(19) ?
C6 C5 H5 119.7(19) ?
C5 C6 C1 118.9(3) ?
C5 C6 C7 135.6(3) ?
C1 C6 C7 105.5(3) ?
N2 C7 C8 120.7(3) ?
N2 C7 C6 131.1(3) yes
C8 C7 C6 108.2(3) ?
N1 C8 C7 108.4(3) yes
N1 C8 C9 122.8(3) yes
C7 C8 C9 128.8(3) yes
C14 C9 C10 118.6(3) ?
C14 C9 C8 121.8(3) ?
C10 C9 C8 119.6(3) ?
C11 C10 C9 120.1(4) ?
C11 C10 H10 122(2) ?
C9 C10 H10 118(2) ?
C10 C11 C12 120.6(4) ?
C10 C11 H11 122(2) ?
C12 C11 H11 117(2) ?
C13 C12 C11 119.6(4) ?
C13 C12 H12 123(3) ?
C11 C12 H12 118(3) ?
C12 C13 C14 120.8(4) ?
C12 C13 H13 121(3) ?
C14 C13 H13 118(3) ?
C13 C14 C9 120.3(4) ?
C13 C14 H14 121(2) ?
C9 C14 H14 118(2) ?
N1 C15 H15A 109.5 ?
N1 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
N1 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
C17 C16 C21 119.0(3) ?
C17 C16 N3 116.0(3) ?
C21 C16 N3 125.0(3) ?
C16 C17 C18 120.9(3) ?
C16 C17 H17 117(2) ?
C18 C17 H17 122(2) ?
C19 C18 C17 118.9(3) ?
C19 C18 H18 123(2) ?
C17 C18 H18 118(2) ?
C18 C19 C20 121.3(3) ?
C18 C19 Cl1 119.5(3) ?
C20 C19 Cl1 119.2(3) ?
C21 C20 C19 119.5(3) ?
C21 C20 H20 124(2) ?
C19 C20 H20 117(2) ?
C20 C21 C16 120.5(3) ?
C20 C21 H21 122(2) ?
C16 C21 H21 117(2) ?
C8' N1' C1' 108.8(3) yes
C8' N1' C15' 126.6(3) yes
C1' N1' C15' 123.5(3) yes
N3' N2' C7' 114.8(3) yes
N2' N3' C16' 112.5(3) yes
C2' C1' N1' 128.9(3) ?
C2' C1' C6' 122.2(3) ?
N1' C1' C6' 108.8(3) ?
C3' C2' C1' 117.2(4) ?
C3' C2' H2' 121(2) ?
C1' C2' H2' 121(2) ?
C2' C3' C4' 121.4(4) ?
C2' C3' H3' 118(2) ?
C4' C3' H3' 120(2) ?
C5' C4' C3' 121.2(4) ?
C5' C4' H4' 121(2) ?
C3' C4' H4' 118(2) ?
C4' C5' C6' 119.2(4) ?
C4' C5' H5' 122(2) ?
C6' C5' H5' 119(2) ?
C5' C6' C1' 118.8(3) ?
C5' C6' C7' 135.4(3) ?
C1' C6' C7' 105.8(3) ?
N2' C7' C8' 120.2(3) ?
N2' C7' C6' 131.9(3) yes
C8' C7' C6' 107.9(3) ?
N1' C8' C7' 108.7(3) yes
N1' C8' C9' 123.0(3) yes
C7' C8' C9' 128.2(3) yes
C10' C9' C14' 118.8(3) ?
C10' C9' C8' 120.5(3) ?
C14' C9' C8' 120.7(3) ?
C11' C10' C9' 120.3(4) ?
C11' C10' H10' 120(2) ?
C9' C10' H10' 119(2) ?
C12' C11' C10' 120.2(4) ?
C12' C11' H11' 121(3) ?
C10' C11' H11' 118(3) ?
C13' C12' C11' 120.5(4) ?
C13' C12' H12' 118(2) ?
C11' C12' H12' 122(2) ?
C12' C13' C14' 119.7(4) ?
C12' C13' H13' 122(3) ?
C14' C13' H13' 119(3) ?
C13' C14' C9' 120.6(4) ?
C13' C14' H14' 121(2) ?
C9' C14' H14' 119(2) ?
N1' C15' H15D 109.5 ?
N1' C15' H15E 109.5 ?
H15D C15' H15E 109.5 ?
N1' C15' H15F 109.5 ?
H15D C15' H15F 109.5 ?
H15E C15' H15F 109.5 ?
C17' C16' C21' 119.4(3) ?
C17' C16' N3' 116.9(3) ?
C21' C16' N3' 123.6(3) ?
C16' C17' C18' 120.9(3) ?
C16' C17' H17' 116(2) ?
C18' C17' H17' 123(2) ?
C19' C18' C17' 118.9(3) ?
C19' C18' H18' 120(2) ?
C17' C18' H18' 121(2) ?
C18' C19' C20' 120.9(3) ?
C18' C19' Cl1' 119.7(3) ?
C20' C19' Cl1' 119.3(3) ?
C19' C20' C21' 120.4(3) ?
C19' C20' H20' 119(2) ?
C21' C20' H20' 121(2) ?
C20' C21' C16' 119.4(3) ?
C20' C21' H21' 121(2) ?
C16' C21' H21' 119(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C19 1.735(3) ?
N1 C8 1.375(3) yes
N1 C1 1.391(4) yes
N1 C15 1.462(4) yes
N2 N3 1.277(3) yes
N2 C7 1.385(3) yes
N3 C16 1.422(4) yes
C1 C2 1.395(4) ?
C1 C6 1.406(4) yes
C2 C3 1.374(5) ?
C2 H2 0.94(3) ?
C3 C4 1.386(6) ?
C3 H3 0.95(4) ?
C4 H4 0.90(4) ?
C5 C4 1.379(5) ?
C5 H5 0.99(3) ?
C6 C5 1.402(4) ?
C7 C8 1.391(4) yes
C7 C6 1.440(4) yes
C8 C9 1.470(4) ?
C9 C14 1.384(5) ?
C9 C10 1.401(4) ?
C10 C11 1.374(5) ?
C10 H10 0.94(3) ?
C11 C12 1.375(6) ?
C11 H11 0.99(4) ?
C12 H12 1.00(5) ?
C13 C12 1.368(6) ?
C13 H13 0.95(4) ?
C14 C13 1.379(5) ?
C14 H14 0.92(3) ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
C16 C17 1.385(4) ?
C16 C21 1.390(4) ?
C17 C18 1.388(5) ?
C17 H17 0.96(3) ?
C18 H18 0.96(4) ?
C19 C18 1.372(5) ?
C19 C20 1.380(5) ?
C20 H20 0.98(4) ?
C21 C20 1.379(4) ?
C21 H21 0.95(3) ?
Cl1' C19' 1.739(3) ?
N1' C1' 1.395(4) yes
N1' C15' 1.455(4) yes
N2' C7' 1.385(4) yes
N3' N2' 1.272(3) yes
N3' C16' 1.428(4) yes
C1' C2' 1.389(4) ?
C2' H2' 0.89(3) ?
C3' C4' 1.388(6) ?
C3' H3' 0.95(4) ?
C3' C2' 1.377(6) ?
C4' H4' 0.95(3) ?
C5' C4' 1.370(5) ?
C5' H5' 0.96(3) ?
C6' C5' 1.393(5) ?
C6' C1' 1.402(4) yes
C7' C6' 1.440(4) yes
C8' N1' 1.372(4) yes
C8' C7' 1.392(4) yes
C8' C9' 1.471(4) ?
C9' C10' 1.388(4) ?
C9' C14' 1.396(4) ?
C10' C11' 1.380(5) ?
C10' H10' 0.94(3) ?
C11' H11' 0.92(4) ?
C12' C11' 1.376(6) ?
C12' H12' 0.89(4) ?
C13' C12' 1.373(6) ?
C13' H13' 0.94(4) ?
C14' C13' 1.381(5) ?
C14' H14' 0.95(4) ?
C15' H15D 0.9600 ?
C15' H15E 0.9600 ?
C15' H15F 0.9600 ?
C16' C17' 1.377(4) ?
C16' C21' 1.389(4) ?
C17' H17' 0.90(3) ?
C18' C19' 1.367(5) ?
C18' C17' 1.384(5) ?
C18' H18' 0.94(3) ?
C20' C19' 1.371(5) ?
C20' C21' 1.378(5) ?
C20' H20' 0.91(3) ?
C21' H21' 0.95(4) ?
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_publ_flag
C1 N1 C8 C7 0.0(3) yes
C15 N1 C8 C7 -173.7(3) ?
C1 N1 C8 C9 -178.8(3) ?
C15 N1 C8 C9 7.4(5) ?
C8 N1 C1 C2 -178.4(3) ?
C15 N1 C1 C2 -4.3(5) ?
C8 N1 C1 C6 0.5(3) yes
C15 N1 C1 C6 174.6(3) ?
N3 N2 C7 C8 -174.3(3) ?
N3 N2 C7 C6 4.0(4) ?
C7 N2 N3 C16 175.4(2) ?
N2 N3 C16 C17 178.3(3) ?
N2 N3 C16 C21 -5.3(4) ?
N1 C1 C6 C5 179.4(3) ?
C2 C1 C6 C5 -1.7(5) ?
N1 C1 C6 C7 -0.8(3) yes
C2 C1 C6 C7 178.2(3) ?
N1 C1 C2 C3 178.2(3) ?
C6 C1 C2 C3 -0.6(5) ?
C1 C2 C3 C4 2.1(5) ?
C2 C3 C4 C5 -1.4(6) ?
C6 C5 C4 C3 -0.9(5) ?
C1 C6 C5 C4 2.4(5) ?
C7 C6 C5 C4 -177.5(3) ?
N2 C7 C6 C5 2.2(6) ?
C8 C7 C6 C5 -179.4(3) ?
N2 C7 C6 C1 -177.7(3) ?
C8 C7 C6 C1 0.8(3) yes
N2 C7 C8 N1 178.1(3) ?
C6 C7 C8 N1 -0.5(3) yes
N2 C7 C8 C9 -3.1(5) ?
C6 C7 C8 C9 178.2(3) ?
N1 C8 C9 C14 42.5(5) ?
C7 C8 C9 C14 -136.1(4) ?
N1 C8 C9 C10 -138.0(3) ?
C7 C8 C9 C10 43.4(5) ?
C10 C9 C14 C13 0.8(5) ?
C8 C9 C14 C13 -179.7(3) ?
C14 C9 C10 C11 -0.2(5) ?
C8 C9 C10 C11 -179.7(3) ?
C9 C10 C11 C12 -0.4(6) ?
C10 C11 C12 C13 0.3(7) ?
C14 C13 C12 C11 0.4(7) ?
C9 C14 C13 C12 -0.9(7) ?
C17 C16 C21 C20 -1.0(5) ?
N3 C16 C21 C20 -177.2(3) ?
C21 C16 C17 C18 0.8(5) ?
N3 C16 C17 C18 177.4(3) ?
C16 C17 C18 C19 -0.4(6) ?
C18 C19 C20 C21 -0.3(5) ?
Cl1 C19 C20 C21 178.8(3) ?
C20 C19 C18 C17 0.1(5) ?
Cl1 C19 C18 C17 -179.0(3) ?
C16 C21 C20 C19 0.7(5) ?
C8' N1' C1' C2' 179.8(4) ?
C15' N1' C1' C2' 11.3(6) ?
C8' N1' C1' C6' 0.2(4) yes
C15' N1' C1' C6' -168.3(3) ?
N3' N2' C7' C8' 177.4(3) ?
N3' N2' C7' C6' -2.5(5) ?
C16' N3' N2' C7' -176.8(3) ?
N2' N3' C16' C17' -161.6(3) ?
N2' N3' C16' C21' 21.9(4) ?
N1' C1' C2' C3' -178.9(4) ?
C6' C1' C2' C3' 0.6(6) ?
C4' C3' C2' C1' -0.1(6) ?
C2' C3' C4' C5' -0.8(7) ?
C6' C5' C4' C3' 1.0(6) ?
C5' C6' C1' C2' -0.4(5) ?
C7' C6' C1' C2' -179.7(3) ?
C5' C6' C1' N1' 179.2(3) ?
C7' C6' C1' N1' -0.1(4) yes
C1' C6' C5' C4' -0.4(5) ?
C7' C6' C5' C4' 178.6(4) ?
N2' C7' C6' C5' 0.7(7) ?
C8' C7' C6' C5' -179.1(4) ?
N2' C7' C6' C1' 179.8(3) ?
C8' C7' C6' C1' -0.1(4) yes
C7' C8' N1' C1' -0.2(4) yes
C9' C8' N1' C1' 176.1(3) ?
C7' C8' N1' C15' 167.8(3) ?
C9' C8' N1' C15' -15.9(5) ?
N1' C8' C9' C10' 136.9(3) ?
C7' C8' C9' C10' -47.5(5) ?
N1' C8' C9' C14' -46.1(5) ?
C7' C8' C9' C14' 129.5(4) ?
N1' C8' C7' N2' -179.7(3) ?
C9' C8' C7' N2' 4.2(5) ?
N1' C8' C7' C6' 0.2(4) yes
C9' C8' C7' C6' -175.9(3) ?
C14' C9' C10' C11' -2.0(5) ?
C8' C9' C10' C11' 175.1(3) ?
C10' C9' C14' C13' 1.6(5) ?
C8' C9' C14' C13' -175.5(3) ?
C9' C10' C11' C12' 0.8(6) ?
C13' C12' C11' C10' 0.7(6) ?
C14' C13' C12' C11' -1.1(6) ?
C9' C14' C13' C12' -0.1(5) ?
C17' C16' C21' C20' 0.8(5) ?
N3' C16' C21' C20' 177.2(3) ?
C21' C16' C17' C18' -2.0(5) ?
N3' C16' C17' C18' -178.6(3) ?
C19' C18' C17' C16' 1.8(6) ?
C17' C18' C19' C20' -0.5(6) ?
C17' C18' C19' Cl1' 178.8(3) ?
C21' C20' C19' C18' -0.7(6) ?
C21' C20' C19' Cl1' -180.0(3) ?
C19' C20' C21' C16' 0.6(6) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 28549991
