#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/47/2224789.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_2224789
loop_
_publ_author_name
'Goh, Jia Hao'
'Fun, Hoong-Kun'
'Vinayaka, A. C.'
'Kalluraya, B.'
_publ_section_title
(E)-1-[(Diphenylamino)methyl]-4-(4-fluorobenzylideneamino)-3-[1-(4-isobutylphenyl)ethyl]-1H-1,2,4-triazole-5(4H)-thione
_journal_coeditor_code           TK2593
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o83
_journal_page_last               o84
_journal_paper_doi               10.1107/S1600536809052039
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C34 H34 F N5 S'
_chemical_formula_moiety         'C34 H34 F N5 S'
_chemical_formula_sum            'C34 H34 F N5 S'
_chemical_formula_weight         563.72
_chemical_name_systematic
;
(E)-1-[(Diphenylamino)methyl]-4-(4-fluorobenzylideneamino)-3-
[1-(4-isobutylphenyl)ethyl]-1H-1,2,4-triazole-5(4H)-thione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 105.1990(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8175(2)
_cell_length_b                   9.95790(10)
_cell_length_c                   27.8344(4)
_cell_measurement_reflns_used    9739
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      34.7
_cell_measurement_theta_min      2.6
_cell_volume                     2893.43(7)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector diffractometer
;
_diffrn_measurement_method       'φ and ω scans'
_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  0.035
_diffrn_reflns_av_sigmaI/netI    0.030
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            58342
_diffrn_reflns_theta_full        32.5
_diffrn_reflns_theta_max         32.50
_diffrn_reflns_theta_min         2.1
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.42
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         10414
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.059
_refine_ls_R_factor_gt           0.044
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0575P)²+0.8906P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.112
_refine_ls_wR_factor_ref         0.120
_reflns_number_gt                8240
_reflns_number_total             10414
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2593.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224789
_cod_database_fobs_code          2224789
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.16117(3) 0.22751(3) 0.589154(11) 0.02485(7) Uani d . 1 . .
F F1 0.52953(8) 0.48389(9) 0.37293(3) 0.03681(19) Uani d . 1 . .
N N1 0.17190(9) 0.50769(9) 0.51987(3) 0.01794(17) Uani d . 1 . .
N N2 0.11972(9) 0.49448(9) 0.56030(3) 0.01672(16) Uani d . 1 . .
N N3 0.04413(9) 0.43808(9) 0.62106(3) 0.01820(17) Uani d . 1 . .
N N4 0.01010(9) 0.57105(9) 0.61131(3) 0.01838(17) Uani d . 1 . .
N N5 0.05479(9) 0.45860(10) 0.70862(3) 0.02075(18) Uani d . 1 . .
C C1 0.29376(11) 0.54223(11) 0.44134(4) 0.0207(2) Uani d . 1 . .
H H1A 0.2273 0.6013 0.4416 0.025 Uiso calc R 1 . .
C C2 0.36276(12) 0.55679(12) 0.40618(4) 0.0244(2) Uani d . 1 . .
H H2A 0.3438 0.6255 0.3828 0.029 Uiso calc R 1 . .
C C3 0.46049(12) 0.46680(12) 0.40667(4) 0.0242(2) Uani d . 1 . .
C C4 0.49201(11) 0.36250(11) 0.43997(4) 0.0227(2) Uani d . 1 . .
H H4A 0.5576 0.3030 0.4390 0.027 Uiso calc R 1 . .
C C5 0.42230(11) 0.34904(11) 0.47520(4) 0.0200(2) Uani d . 1 . .
H H5A 0.4415 0.2793 0.4982 0.024 Uiso calc R 1 . .
C C6 0.32382(10) 0.43867(10) 0.47658(4) 0.01744(18) Uani d . 1 . .
C C7 0.26117(10) 0.42571(10) 0.51707(4) 0.01848(19) Uani d . 1 . .
H H7A 0.2861 0.3581 0.5407 0.022 Uiso calc R 1 . .
C C8 0.11087(10) 0.38574(10) 0.59048(4) 0.01786(19) Uani d . 1 . .
C C9 0.05599(10) 0.60207(10) 0.57402(4) 0.01684(18) Uani d . 1 . .
C C10 0.04846(10) 0.73715(10) 0.55006(4) 0.01775(19) Uani d . 1 . .
H H10A 0.0237 0.7246 0.5139 0.021 Uiso calc R 1 . .
C C11 0.17695(10) 0.80893(10) 0.56429(4) 0.01719(18) Uani d . 1 . .
C C12 0.24975(11) 0.81605(11) 0.61379(4) 0.0201(2) Uani d . 1 . .
H H12A 0.2251 0.7669 0.6381 0.024 Uiso calc R 1 . .
C C13 0.35875(11) 0.89604(11) 0.62690(4) 0.0211(2) Uani d . 1 . .
H H13A 0.4056 0.9002 0.6601 0.025 Uiso calc R 1 . .
C C14 0.39935(11) 0.97024(10) 0.59134(4) 0.0202(2) Uani d . 1 . .
C C15 0.32793(12) 0.95927(11) 0.54167(4) 0.0221(2) Uani d . 1 . .
H H15A 0.3543 1.0058 0.5171 0.026 Uiso calc R 1 . .
C C16 0.21845(11) 0.88019(11) 0.52838(4) 0.0204(2) Uani d . 1 . .
H H16A 0.1724 0.8748 0.4952 0.024 Uiso calc R 1 . .
C C17 0.51678(11) 1.05862(11) 0.60507(4) 0.0229(2) Uani d . 1 . .
H H17A 0.5272 1.0919 0.6386 0.028 Uiso calc R 1 . .
H H17B 0.5030 1.1355 0.5829 0.028 Uiso calc R 1 . .
C C18 0.64135(11) 0.98818(10) 0.60244(4) 0.0200(2) Uani d . 1 . .
H H18A 0.6264 0.9450 0.5698 0.024 Uiso calc R 1 . .
C C19 0.74893(12) 1.09067(12) 0.60727(5) 0.0260(2) Uani d . 1 . .
H H19A 0.8259 1.0454 0.6054 0.039 Uiso calc R 1 . .
H H19B 0.7634 1.1361 0.6387 0.039 Uiso calc R 1 . .
H H19C 0.7251 1.1549 0.5807 0.039 Uiso calc R 1 . .
C C20 0.68007(12) 0.87972(12) 0.64228(4) 0.0241(2) Uani d . 1 . .
H H20A 0.7545 0.8334 0.6382 0.036 Uiso calc R 1 . .
H H20B 0.6109 0.8170 0.6390 0.036 Uiso calc R 1 . .
H H20C 0.6991 0.9205 0.6746 0.036 Uiso calc R 1 . .
C C21 -0.05414(11) 0.82343(11) 0.56409(5) 0.0238(2) Uani d . 1 . .
H H21A -0.1359 0.7798 0.5531 0.036 Uiso calc R 1 . .
H H21B -0.0580 0.9097 0.5484 0.036 Uiso calc R 1 . .
H H21C -0.0328 0.8348 0.5996 0.036 Uiso calc R 1 . .
C C22 0.02287(12) 0.37238(11) 0.66559(4) 0.0217(2) Uani d . 1 . .
H H22A -0.0663 0.3461 0.6590 0.026 Uiso calc R 1 . .
H H22B 0.0746 0.2916 0.6726 0.026 Uiso calc R 1 . .
C C23 -0.04449(10) 0.50037(10) 0.73041(4) 0.01839(19) Uani d . 1 . .
C C24 -0.15516(11) 0.56251(12) 0.70258(4) 0.0222(2) Uani d . 1 . .
H H24A -0.1661 0.5789 0.6688 0.027 Uiso calc R 1 . .
C C25 -0.24961(11) 0.60002(12) 0.72568(4) 0.0240(2) Uani d . 1 . .
H H25A -0.3246 0.6400 0.7070 0.029 Uiso calc R 1 . .
C C26 -0.23290(11) 0.57828(11) 0.77618(4) 0.0218(2) Uani d . 1 . .
H H26A -0.2961 0.6044 0.7914 0.026 Uiso calc R 1 . .
C C27 -0.12167(11) 0.51754(11) 0.80400(4) 0.0218(2) Uani d . 1 . .
H H27A -0.1100 0.5035 0.8379 0.026 Uiso calc R 1 . .
C C28 -0.02782(11) 0.47779(11) 0.78124(4) 0.0209(2) Uani d . 1 . .
H H28A 0.0462 0.4361 0.7998 0.025 Uiso calc R 1 . .
C C29 0.17503(10) 0.52279(11) 0.72258(4) 0.0194(2) Uani d . 1 . .
C C30 0.18674(11) 0.64932(11) 0.74534(4) 0.0215(2) Uani d . 1 . .
H H30A 0.1152 0.6899 0.7516 0.026 Uiso calc R 1 . .
C C31 0.30399(12) 0.71451(12) 0.75856(5) 0.0258(2) Uani d . 1 . .
H H31A 0.3105 0.7984 0.7737 0.031 Uiso calc R 1 . .
C C32 0.41226(12) 0.65524(13) 0.74936(5) 0.0277(2) Uani d . 1 . .
H H32A 0.4910 0.6988 0.7583 0.033 Uiso calc R 1 . .
C C33 0.40086(12) 0.53055(13) 0.72666(5) 0.0267(2) Uani d . 1 . .
H H33A 0.4729 0.4904 0.7206 0.032 Uiso calc R 1 . .
C C34 0.28381(11) 0.46417(12) 0.71282(4) 0.0235(2) Uani d . 1 . .
H H34A 0.2777 0.3811 0.6971 0.028 Uiso calc R 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N1 N2 . . 117.44(9) ?
C9 N2 C8 . . 108.60(9) ?
C9 N2 N1 . . 119.22(8) ?
C8 N2 N1 . . 132.06(8) ?
C8 N3 N4 . . 113.78(9) ?
C8 N3 C22 . . 125.73(9) ?
N4 N3 C22 . . 119.91(8) ?
C9 N4 N3 . . 104.27(8) ?
C29 N5 C23 . . 119.58(9) ?
C29 N5 C22 . . 120.16(9) ?
C23 N5 C22 . . 118.96(9) ?
C2 C1 C6 . . 120.16(10) ?
C2 C1 H1A . . 119.9 ?
C6 C1 H1A . . 119.9 ?
C3 C2 C1 . . 118.50(11) ?
C3 C2 H2A . . 120.7 ?
C1 C2 H2A . . 120.7 ?
F1 C3 C4 . . 118.56(11) ?
F1 C3 C2 . . 118.06(11) ?
C4 C3 C2 . . 123.37(11) ?
C3 C4 C5 . . 117.63(10) ?
C3 C4 H4A . . 121.2 ?
C5 C4 H4A . . 121.2 ?
C4 C5 C6 . . 121.03(10) ?
C4 C5 H5A . . 119.5 ?
C6 C5 H5A . . 119.5 ?
C5 C6 C1 . . 119.29(10) ?
C5 C6 C7 . . 118.32(10) ?
C1 C6 C7 . . 122.27(10) ?
N1 C7 C6 . . 119.89(10) ?
N1 C7 H7A . . 120.1 ?
C6 C7 H7A . . 120.1 ?
N3 C8 N2 . . 102.26(8) ?
N3 C8 S1 . . 127.33(8) ?
N2 C8 S1 . . 130.34(8) ?
N4 C9 N2 . . 111.06(9) ?
N4 C9 C10 . . 125.65(9) ?
N2 C9 C10 . . 123.22(9) ?
C9 C10 C11 . . 111.58(8) ?
C9 C10 C21 . . 110.44(9) ?
C11 C10 C21 . . 110.10(9) ?
C9 C10 H10A . . 108.2 ?
C11 C10 H10A . . 108.2 ?
C21 C10 H10A . . 108.2 ?
C16 C11 C12 . . 118.50(10) ?
C16 C11 C10 . . 119.83(9) ?
C12 C11 C10 . . 121.39(9) ?
C13 C12 C11 . . 120.51(10) ?
C13 C12 H12A . . 119.7 ?
C11 C12 H12A . . 119.7 ?
C12 C13 C14 . . 121.35(10) ?
C12 C13 H13A . . 119.3 ?
C14 C13 H13A . . 119.3 ?
C13 C14 C15 . . 117.67(10) ?
C13 C14 C17 . . 121.98(10) ?
C15 C14 C17 . . 120.35(10) ?
C16 C15 C14 . . 121.23(10) ?
C16 C15 H15A . . 119.4 ?
C14 C15 H15A . . 119.4 ?
C15 C16 C11 . . 120.69(10) ?
C15 C16 H16A . . 119.7 ?
C11 C16 H16A . . 119.7 ?
C14 C17 C18 . . 114.31(9) ?
C14 C17 H17A . . 108.7 ?
C18 C17 H17A . . 108.7 ?
C14 C17 H17B . . 108.7 ?
C18 C17 H17B . . 108.7 ?
H17A C17 H17B . . 107.6 ?
C20 C18 C19 . . 110.58(10) ?
C20 C18 C17 . . 111.43(9) ?
C19 C18 C17 . . 110.37(9) ?
C20 C18 H18A . . 108.1 ?
C19 C18 H18A . . 108.1 ?
C17 C18 H18A . . 108.1 ?
C18 C19 H19A . . 109.5 ?
C18 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C18 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C18 C20 H20A . . 109.5 ?
C18 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C18 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C10 C21 H21A . . 109.5 ?
C10 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C10 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
N5 C22 N3 . . 112.27(9) ?
N5 C22 H22A . . 109.1 ?
N3 C22 H22A . . 109.1 ?
N5 C22 H22B . . 109.1 ?
N3 C22 H22B . . 109.1 ?
H22A C22 H22B . . 107.9 ?
C24 C23 C28 . . 120.00(10) ?
C24 C23 N5 . . 121.85(10) ?
C28 C23 N5 . . 118.16(10) ?
C23 C24 C25 . . 119.42(10) ?
C23 C24 H24A . . 120.3 ?
C25 C24 H24A . . 120.3 ?
C26 C25 C24 . . 120.64(11) ?
C26 C25 H25A . . 119.7 ?
C24 C25 H25A . . 119.7 ?
C25 C26 C27 . . 119.83(11) ?
C25 C26 H26A . . 120.1 ?
C27 C26 H26A . . 120.1 ?
C26 C27 C28 . . 120.04(10) ?
C26 C27 H27A . . 120.0 ?
C28 C27 H27A . . 120.0 ?
C27 C28 C23 . . 120.06(10) ?
C27 C28 H28A . . 120.0 ?
C23 C28 H28A . . 120.0 ?
C30 C29 C34 . . 118.75(10) ?
C30 C29 N5 . . 120.00(10) ?
C34 C29 N5 . . 121.22(10) ?
C31 C30 C29 . . 120.61(11) ?
C31 C30 H30A . . 119.7 ?
C29 C30 H30A . . 119.7 ?
C30 C31 C32 . . 120.49(11) ?
C30 C31 H31A . . 119.8 ?
C32 C31 H31A . . 119.8 ?
C33 C32 C31 . . 119.02(11) ?
C33 C32 H32A . . 120.5 ?
C31 C32 H32A . . 120.5 ?
C32 C33 C34 . . 121.25(11) ?
C32 C33 H33A . . 119.4 ?
C34 C33 H33A . . 119.4 ?
C33 C34 C29 . . 119.86(11) ?
C33 C34 H34A . . 120.1 ?
C29 C34 H34A . . 120.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C8 . 1.6705(11) ?
F1 C3 . 1.3552(13) ?
N1 C7 . 1.2824(14) ?
N1 N2 . 1.3910(12) ?
N2 C9 . 1.3809(13) ?
N2 C8 . 1.3892(13) ?
N3 C8 . 1.3562(13) ?
N3 N4 . 1.3821(12) ?
N3 C22 . 1.4720(14) ?
N4 C9 . 1.2999(14) ?
N5 C29 . 1.4095(15) ?
N5 C23 . 1.4267(14) ?
N5 C22 . 1.4401(14) ?
C1 C2 . 1.3854(16) ?
C1 C6 . 1.4014(15) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.3832(17) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.3742(17) ?
C4 C5 . 1.3914(16) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.3980(15) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.4650(15) ?
C7 H7A . 0.9300 ?
C9 C10 . 1.4940(14) ?
C10 C11 . 1.5202(15) ?
C10 C21 . 1.5330(15) ?
C10 H10A . 0.9800 ?
C11 C16 . 1.3926(15) ?
C11 C12 . 1.3983(15) ?
C12 C13 . 1.3900(16) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.3953(16) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.4000(16) ?
C14 C17 . 1.5098(16) ?
C15 C16 . 1.3891(16) ?
C15 H15A . 0.9300 ?
C16 H16A . 0.9300 ?
C17 C18 . 1.5378(16) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 C20 . 1.5257(15) ?
C18 C19 . 1.5271(16) ?
C18 H18A . 0.9800 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 0.9600 ?
C22 H22A . 0.9700 ?
C22 H22B . 0.9700 ?
C23 C24 . 1.3891(16) ?
C23 C28 . 1.3968(15) ?
C24 C25 . 1.3932(16) ?
C24 H24A . 0.9300 ?
C25 C26 . 1.3863(16) ?
C25 H25A . 0.9300 ?
C26 C27 . 1.3874(16) ?
C26 H26A . 0.9300 ?
C27 C28 . 1.3879(15) ?
C27 H27A . 0.9300 ?
C28 H28A . 0.9300 ?
C29 C30 . 1.4010(16) ?
C29 C34 . 1.4025(15) ?
C30 C31 . 1.3859(17) ?
C30 H30A . 0.9300 ?
C31 C32 . 1.3939(18) ?
C31 H31A . 0.9300 ?
C32 C33 . 1.3839(19) ?
C32 H32A . 0.9300 ?
C33 C34 . 1.3902(17) ?
C33 H33A . 0.9300 ?
C34 H34A . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C7 H7A S1 . 0.93 2.51 3.1983(11) 131 yes
C4 H4A Cg1 3_666 0.93 2.65 3.5688(13) 169 yes
C20 H20C Cg2 2_656 0.96 2.99 3.9291(12) 166 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 N2 C9 . . . . 159.24(10) ?
C7 N1 N2 C8 . . . . -25.33(16) ?
C8 N3 N4 C9 . . . . 0.16(12) ?
C22 N3 N4 C9 . . . . 171.99(10) ?
C6 C1 C2 C3 . . . . 0.36(17) ?
C1 C2 C3 F1 . . . . -178.37(10) ?
C1 C2 C3 C4 . . . . 0.72(18) ?
F1 C3 C4 C5 . . . . 178.21(10) ?
C2 C3 C4 C5 . . . . -0.87(18) ?
C3 C4 C5 C6 . . . . -0.04(16) ?
C4 C5 C6 C1 . . . . 1.07(16) ?
C4 C5 C6 C7 . . . . -175.07(10) ?
C2 C1 C6 C5 . . . . -1.22(16) ?
C2 C1 C6 C7 . . . . 174.75(11) ?
N2 N1 C7 C6 . . . . -177.20(9) ?
C5 C6 C7 N1 . . . . 178.88(10) ?
C1 C6 C7 N1 . . . . 2.87(16) ?
N4 N3 C8 N2 . . . . 0.73(12) ?
C22 N3 C8 N2 . . . . -170.53(10) ?
N4 N3 C8 S1 . . . . -176.59(8) ?
C22 N3 C8 S1 . . . . 12.14(16) ?
C9 N2 C8 N3 . . . . -1.31(11) ?
N1 N2 C8 N3 . . . . -177.11(10) ?
C9 N2 C8 S1 . . . . 175.90(9) ?
N1 N2 C8 S1 . . . . 0.10(18) ?
N3 N4 C9 N2 . . . . -1.03(12) ?
N3 N4 C9 C10 . . . . -178.02(10) ?
C8 N2 C9 N4 . . . . 1.55(12) ?
N1 N2 C9 N4 . . . . 177.97(9) ?
C8 N2 C9 C10 . . . . 178.62(10) ?
N1 N2 C9 C10 . . . . -4.95(15) ?
N4 C9 C10 C11 . . . . 105.64(12) ?
N2 C9 C10 C11 . . . . -70.99(13) ?
N4 C9 C10 C21 . . . . -17.17(15) ?
N2 C9 C10 C21 . . . . 166.20(10) ?
C9 C10 C11 C16 . . . . 138.70(10) ?
C21 C10 C11 C16 . . . . -98.30(11) ?
C9 C10 C11 C12 . . . . -47.47(13) ?
C21 C10 C11 C12 . . . . 75.53(12) ?
C16 C11 C12 C13 . . . . 2.04(16) ?
C10 C11 C12 C13 . . . . -171.87(10) ?
C11 C12 C13 C14 . . . . -0.57(17) ?
C12 C13 C14 C15 . . . . -1.30(16) ?
C12 C13 C14 C17 . . . . 179.39(10) ?
C13 C14 C15 C16 . . . . 1.72(16) ?
C17 C14 C15 C16 . . . . -178.96(10) ?
C14 C15 C16 C11 . . . . -0.26(17) ?
+C12 C11 C16 C15 . . . . -1.62(16) ?
C10 C11 C16 C15 . . . . 172.38(10) ?
C13 C14 C17 C18 . . . . 91.25(13) ?
C15 C14 C17 C18 . . . . -88.04(13) ?
C14 C17 C18 C20 . . . . -67.35(12) ?
C14 C17 C18 C19 . . . . 169.38(10) ?
C29 N5 C22 N3 . . . . -51.66(14) ?
C23 N5 C22 N3 . . . . 115.30(11) ?
C8 N3 C22 N5 . . . . 129.58(11) ?
N4 N3 C22 N5 . . . . -41.19(14) ?
C29 N5 C23 C24 . . . . 113.07(12) ?
C22 N5 C23 C24 . . . . -53.97(15) ?
C29 N5 C23 C28 . . . . -66.63(14) ?
C22 N5 C23 C28 . . . . 126.33(11) ?
C28 C23 C24 C25 . . . . -0.94(17) ?
N5 C23 C24 C25 . . . . 179.36(10) ?
C23 C24 C25 C26 . . . . 1.27(18) ?
C24 C25 C26 C27 . . . . -0.57(18) ?
C25 C26 C27 C28 . . . . -0.47(17) ?
C26 C27 C28 C23 . . . . 0.79(17) ?
C24 C23 C28 C27 . . . . -0.08(17) ?
N5 C23 C28 C27 . . . . 179.62(10) ?
C23 N5 C29 C30 . . . . -18.94(15) ?
C22 N5 C29 C30 . . . . 147.93(11) ?
C23 N5 C29 C34 . . . . 162.97(10) ?
C22 N5 C29 C34 . . . . -30.15(15) ?
C34 C29 C30 C31 . . . . -0.87(17) ?
N5 C29 C30 C31 . . . . -178.99(10) ?
C29 C30 C31 C32 . . . . 0.09(18) ?
C30 C31 C32 C33 . . . . 0.22(18) ?
C31 C32 C33 C34 . . . . 0.25(18) ?
C32 C33 C34 C29 . . . . -1.04(18) ?
C30 C29 C34 C33 . . . . 1.33(17) ?
N5 C29 C34 C33 . . . . 179.43(10) ?
