##############################################################################
### ###
### Electronic paper (Acta Crystallographica Section E) ###
### ###
##############################################################################
# #
# This CIF contains the data in a paper accepted for publication in Acta #
# Crystallographica Section E. It conforms to the requirements of Notes #
# for Authors for Section E, and has been peer reviewed under the auspices #
# of the IUCr Commission on Journals. #
# #
# Full details of the Crystallographic Information File format #
# are given in the paper "The Crystallographic Information File (CIF): #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H. #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. #
# #
# The current version of the core CIF dictionary is obtainable from #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4. #
# #
# Software is freely available for graphical display of the structure(s) in #
# this CIF. For information consult the CIF home page http://www.iucr.org/ #
# cif/home.html #
# #
# This file may be used for bona fide research purposes within the #
# scientific community so long as proper attribution is given to the journal #
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##############################################################################
data_global
_audit_creation_method 'form.cif (version 2.0)'
_journal_data_validation_number ?
_journal_date_recd_electronic 2008-11-06
_journal_date_accepted 2008-12-01
_journal_name_full 'Acta Crystallographica, Section E'
_journal_year 2009
_journal_volume 65
_journal_issue 1
_journal_page_first o48
_journal_page_last o48
_journal_paper_category QO
_journal_coeditor_code BI2320
_publ_contact_author_name 'Hoong-Kun Fun'
_publ_contact_author_address
;
X-ray Crystallography Unit
School of Physics
Universiti Sains Malaysia
11800 USM, Penang
MALAYSIA
;
_publ_contact_author_email hkfun@usm.my
_publ_contact_author_fax '604 6579150'
_publ_contact_author_phone '604 6533652'
_publ_section_title
;\
3-Benzamidomethyl-4-[(E)-2-chlorobenzylideneamino]-1H-1,2,4-\
triazole-5(4H)-thione
;
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
'Hoong-Kun Fun' .
; X-ray Crystallography Unit
School of Physics
Universiti Sains Malaysia
11800 USM, Penang
Malaysia
;
'Samuel Robinson Jebas'
;
Permanent address: Department of Physics,
Karunya University,
Karunya Nagar,
Coimbatore 641 114,
India.
;
;
X-ray Crystallography Unit
School of Physics
Universiti Sains Malaysia
11800 USM, Penang
Malaysia
;
'Jyothi N. Rao' .
;
Department of Studies in Chemistry,
Mangalore University,
Mangalagangotri,
Mangalore 574 199,
India
;
'Kalluraya, B.' .
;
Department of Studies in Chemistry,
Mangalore University,
Mangalagangotri,
Mangalore 574 199,
India
;
data_I
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
3-Benzamidomethyl-4-[(E)-2-chlorobenzylideneamino]-1H-1,2,4-
triazole-5(4H)-thione
;
_chemical_name_common ?
_chemical_formula_moiety 'C17 H14 Cl N5 O S'
_chemical_formula_sum 'C17 H14 Cl N5 O S'
_chemical_formula_iupac 'C17 H14 Cl N5 O S'
_chemical_formula_weight 371.84
_chemical_melting_point ?
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/c'
_symmetry_space_group_name_Hall '-P 2ybc'
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'
_cell_length_a 17.0185(6)
_cell_length_b 8.0905(3)
_cell_length_c 12.8292(5)
_cell_angle_alpha 90.00
_cell_angle_beta 105.962(2)
_cell_angle_gamma 90.00
_cell_volume 1698.32(11)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 9004
_cell_measurement_theta_min 2.62
_cell_measurement_theta_max 26.25
_cell_measurement_temperature 100.0(10)
_exptl_crystal_description 'plate'
_exptl_crystal_colour 'colourless'
_exptl_crystal_size_max 0.70
_exptl_crystal_size_mid 0.48
_exptl_crystal_size_min 0.15
_exptl_crystal_density_diffrn 1.454
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 768
_exptl_absorpt_coefficient_mu 0.364
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min 0.7848
_exptl_absorpt_correction_T_max 0.9485
_exptl_special_details
;
;
_diffrn_ambient_temperature 100.0(10)
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker SMART APEXII CCD'
_diffrn_measurement_method '\f and \w'
_diffrn_reflns_number 57891
_diffrn_reflns_av_R_equivalents 0.0254
_diffrn_reflns_av_sigmaI/netI 0.0162
_diffrn_reflns_theta_min 1.24
_diffrn_reflns_theta_max 35.00
_diffrn_reflns_theta_full 35.00
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min -27
_diffrn_reflns_limit_h_max 27
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_l_min -20
_diffrn_reflns_limit_l_max 20
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^2^, conventional
R-factors R are based on F, with F set to zero for
negative F^2^. The threshold expression of F^2^ >
\s(F^2^) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^2^ are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total 7463
_reflns_number_gt 6349
_reflns_threshold_expression I>2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0409
_refine_ls_R_factor_gt 0.0326
_refine_ls_wR_factor_gt 0.0883
_refine_ls_wR_factor_ref 0.0984
_refine_ls_goodness_of_fit_ref 1.089
_refine_ls_restrained_S_all 1.089
_refine_ls_number_reflns 7463
_refine_ls_number_parameters 234
_refine_ls_number_restraints 2
_refine_ls_hydrogen_treatment mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0502P)^2^+0.4785P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.004
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.590
_refine_diff_density_min -0.226
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
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'
'Cl' 'Cl' 0.1484 0.1585
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection 'APEX2 (Bruker, 2005)'
_computing_cell_refinement 'SAINT (Bruker, 2005)'
_computing_data_reduction 'SAINT (Bruker, 2005)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003)
;
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
Cl Cl1 1.007210(13) 1.03657(3) 0.261198(17) 0.02066(5) Uani d . 1 . .
S S1 0.757666(14) 1.12198(3) 0.021681(19) 0.02205(6) Uani d . 1 . .
O O1 0.52774(4) 1.20878(8) 0.36983(5) 0.01823(12) Uani d . 1 . .
N N1 0.52114(5) 0.94734(9) 0.30979(6) 0.01683(13) Uani d D 1 . .
N N2 0.56478(5) 1.09220(10) 0.13014(6) 0.01817(13) Uani d . 1 . .
N N3 0.60840(5) 1.13484(10) 0.05794(6) 0.01859(14) Uani d D 1 . .
N N4 0.69550(4) 1.02508(9) 0.19194(6) 0.01486(12) Uani d . 1 . .
N N5 0.75857(4) 0.95136(10) 0.26923(6) 0.01636(13) Uani d . 1 . .
C C1 0.37543(6) 1.16562(13) 0.41825(8) 0.02102(16) Uani d . 1 . .
H H1A 0.4129 1.2333 0.4659 0.025 Uiso calc R 1 . .
C C2 0.29456(7) 1.16030(15) 0.42187(9) 0.0288(2) Uani d . 1 . .
H H2A 0.2779 1.2232 0.4726 0.035 Uiso calc R 1 . .
C C3 0.23860(7) 1.06069(16) 0.34943(11) 0.0332(3) Uani d . 1 . .
H H3A 0.1846 1.0569 0.3522 0.040 Uiso calc R 1 . .
C C4 0.26273(6) 0.96688(15) 0.27305(10) 0.0308(2) Uani d . 1 . .
H H4A 0.2247 0.9019 0.2241 0.037 Uiso calc R 1 . .
C C5 0.34392(6) 0.96984(12) 0.26950(8) 0.02199(17) Uani d . 1 . .
H H5A 0.3603 0.9064 0.2188 0.026 Uiso calc R 1 . .
C C6 0.40030(5) 1.06870(11) 0.34268(7) 0.01574(14) Uani d . 1 . .
C C7 0.48744(5) 1.07999(10) 0.34185(6) 0.01337(13) Uani d . 1 . .
C C8 0.60617(5) 0.94817(11) 0.30987(7) 0.01689(14) Uani d . 1 . .
H H8A 0.6263 0.8354 0.3162 0.020 Uiso calc R 1 . .
H H8B 0.6376 1.0090 0.3727 0.020 Uiso calc R 1 . .
C C9 0.61919(5) 1.02410(10) 0.20985(7) 0.01548(14) Uani d . 1 . .
C C10 0.68828(5) 1.09511(11) 0.09059(7) 0.01650(14) Uani d . 1 . .
C C11 0.83182(5) 0.96240(11) 0.26128(7) 0.01659(14) Uani d . 1 . .
H H11A 0.8436 1.0204 0.2048 0.020 Uiso calc R 1 . .
C C12 0.89642(5) 0.87989(10) 0.34477(6) 0.01453(13) Uani d . 1 . .
C C13 0.97907(5) 0.90723(10) 0.35310(6) 0.01472(13) Uani d . 1 . .
C C14 1.04079(5) 0.83357(11) 0.43414(7) 0.01758(15) Uani d . 1 . .
H H14A 1.0954 0.8540 0.4387 0.021 Uiso calc R 1 . .
C C15 1.01981(6) 0.72926(11) 0.50811(7) 0.01963(16) Uani d . 1 . .
H H15A 1.0606 0.6804 0.5630 0.024 Uiso calc R 1 . .
C C16 0.93781(6) 0.69731(12) 0.50042(7) 0.02018(16) Uani d . 1 . .
H H16A 0.9240 0.6264 0.5497 0.024 Uiso calc R 1 . .
C C17 0.87707(5) 0.77125(11) 0.41949(7) 0.01766(14) Uani d . 1 . .
H H17A 0.8226 0.7487 0.4145 0.021 Uiso calc R 1 . .
H H1N3 0.5848(9) 1.1788(19) -0.0026(9) 0.034(4) Uiso d D 1 . .
H H1N1 0.4932(9) 0.8627(15) 0.2855(13) 0.040(4) Uiso d D 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.01679(9) 0.02638(11) 0.01858(9) -0.00361(7) 0.00446(7) 0.00349(7)
S1 0.01723(10) 0.03144(12) 0.01831(10) 0.00069(8) 0.00629(7) 0.00525(8)
O1 0.0181(3) 0.0162(3) 0.0190(3) -0.0035(2) 0.0027(2) -0.0028(2)
N1 0.0142(3) 0.0155(3) 0.0217(3) -0.0019(2) 0.0065(2) -0.0035(2)
N2 0.0139(3) 0.0220(3) 0.0183(3) 0.0027(3) 0.0040(2) 0.0024(3)
N3 0.0147(3) 0.0234(3) 0.0168(3) 0.0032(3) 0.0030(2) 0.0044(3)
N4 0.0115(3) 0.0184(3) 0.0143(3) 0.0024(2) 0.0029(2) 0.0018(2)
N5 0.0130(3) 0.0202(3) 0.0147(3) 0.0035(2) 0.0020(2) 0.0013(2)
C1 0.0211(4) 0.0247(4) 0.0198(4) 0.0061(3) 0.0098(3) 0.0049(3)
C2 0.0242(5) 0.0374(5) 0.0302(5) 0.0127(4) 0.0163(4) 0.0145(4)
C3 0.0160(4) 0.0428(6) 0.0430(6) 0.0060(4) 0.0117(4) 0.0218(5)
C4 0.0146(4) 0.0349(6) 0.0396(6) -0.0037(4) 0.0015(4) 0.0115(4)
C5 0.0158(4) 0.0223(4) 0.0255(4) -0.0022(3) 0.0017(3) 0.0029(3)
C6 0.0135(3) 0.0171(3) 0.0170(3) 0.0011(3) 0.0049(3) 0.0037(3)
C7 0.0137(3) 0.0147(3) 0.0115(3) -0.0003(2) 0.0032(2) 0.0006(2)
C8 0.0138(3) 0.0203(4) 0.0173(3) 0.0020(3) 0.0055(3) 0.0012(3)
C9 0.0125(3) 0.0175(3) 0.0165(3) 0.0018(3) 0.0040(3) 0.0000(3)
C10 0.0148(3) 0.0184(3) 0.0155(3) 0.0009(3) 0.0029(3) 0.0014(3)
C11 0.0134(3) 0.0196(4) 0.0160(3) 0.0014(3) 0.0028(3) 0.0018(3)
C12 0.0126(3) 0.0161(3) 0.0143(3) 0.0014(2) 0.0027(2) -0.0004(2)
C13 0.0135(3) 0.0161(3) 0.0143(3) 0.0009(3) 0.0032(2) -0.0006(2)
C14 0.0135(3) 0.0193(4) 0.0180(3) 0.0028(3) 0.0011(3) -0.0015(3)
C15 0.0192(4) 0.0188(4) 0.0184(3) 0.0046(3) 0.0008(3) 0.0018(3)
C16 0.0218(4) 0.0196(4) 0.0187(4) 0.0020(3) 0.0048(3) 0.0038(3)
C17 0.0160(3) 0.0196(4) 0.0177(3) 0.0008(3) 0.0051(3) 0.0016(3)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
Cl1 C13 . 1.7393(9) ?
S1 C10 . 1.6726(9) ?
O1 C7 . 1.2449(10) ?
N1 C7 . 1.3340(11) ?
N1 C8 . 1.4468(11) ?
N1 H1N1 . 0.840(10)
?
N2 C9 . 1.2984(11) ?
N2 N3 . 1.3807(11) ?
N3 C10 . 1.3467(11) ?
N3 H1N3 . 0.850(10)
?
N4 C9 . 1.3797(11) ?
N4 N5 . 1.3804(10) ?
N4 C10 . 1.3924(11) ?
N5 C11 . 1.2816(11) ?
C1 C2 . 1.3905(14) ?
C1 C6 . 1.3999(13) ?
C1 H1A . 0.930 ?
C2 C3 . 1.3904(19) ?
C2 H2A . 0.930 ?
C3 C4 . 1.3879(19) ?
C3 H3A . 0.930 ?
C4 C5 . 1.3951(14) ?
C4 H4A . 0.930 ?
C5 C6 . 1.3951(13) ?
C5 H5A . 0.930 ?
C6 C7 . 1.4887(11) ?
C8 C9 . 1.4930(12) ?
C8 H8A . 0.970 ?
C8 H8B . 0.970 ?
C11 C12 . 1.4677(12) ?
C11 H11A . 0.930 ?
C12 C13 . 1.3987(11) ?
C12 C17 . 1.4047(12) ?
C13 C14 . 1.3924(12) ?
C14 C15 . 1.3879(13) ?
C14 H14A . 0.930 ?
C15 C16 . 1.3958(13) ?
C15 H15A . 0.930 ?
C16 C17 . 1.3836(12) ?
C16 H16A . 0.930 ?
C17 H17A . 0.930 ?
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 C8 . . 120.72(7) ?
C7 N1 H1N1 . . 121.3(12) ?
C8 N1 H1N1 . . 117.8(12) ?
C9 N2 N3 . . 103.64(7) ?
C10 N3 N2 . . 114.49(7) ?
C10 N3 H1N3 . . 124.6(11) ?
N2 N3 H1N3 . . 120.8(11) ?
C9 N4 N5 . . 117.35(7) ?
C9 N4 C10 . . 108.21(7) ?
N5 N4 C10 . . 134.27(7) ?
C11 N5 N4 . . 119.60(7) ?
C2 C1 C6 . . 119.76(10) ?
C2 C1 H1A . . 120.1 ?
C6 C1 H1A . . 120.1 ?
C3 C2 C1 . . 119.87(10) ?
C3 C2 H2A . . 120.1 ?
C1 C2 H2A . . 120.1 ?
C4 C3 C2 . . 120.50(10) ?
C4 C3 H3A . . 119.7 ?
C2 C3 H3A . . 119.7 ?
C3 C4 C5 . . 120.11(11) ?
C3 C4 H4A . . 119.9 ?
C5 C4 H4A . . 119.9 ?
C6 C5 C4 . . 119.47(10) ?
C6 C5 H5A . . 120.3 ?
C4 C5 H5A . . 120.3 ?
C5 C6 C1 . . 120.28(8) ?
C5 C6 C7 . . 122.17(8) ?
C1 C6 C7 . . 117.52(8) ?
O1 C7 N1 . . 120.84(8) ?
O1 C7 C6 . . 121.35(8) ?
N1 C7 C6 . . 117.81(7) ?
N1 C8 C9 . . 112.71(7) ?
N1 C8 H8A . . 109.0 ?
C9 C8 H8A . . 109.0 ?
N1 C8 H8B . . 109.0 ?
C9 C8 H8B . . 109.0 ?
H8A C8 H8B . . 107.8 ?
N2 C9 N4 . . 111.50(7) ?
N2 C9 C8 . . 127.53(8) ?
N4 C9 C8 . . 120.96(7) ?
N3 C10 N4 . . 102.12(7) ?
N3 C10 S1 . . 127.13(7) ?
N4 C10 S1 . . 130.74(7) ?
N5 C11 C12 . . 117.39(8) ?
N5 C11 H11A . . 121.3 ?
C12 C11 H11A . . 121.3 ?
C13 C12 C17 . . 117.80(7) ?
C13 C12 C11 . . 121.30(7) ?
C17 C12 C11 . . 120.90(8) ?
C14 C13 C12 . . 121.71(8) ?
C14 C13 Cl1 . . 118.16(6) ?
C12 C13 Cl1 . . 120.13(6) ?
C15 C14 C13 . . 119.19(8) ?
C15 C14 H14A . . 120.4 ?
C13 C14 H14A . . 120.4 ?
C14 C15 C16 . . 120.29(8) ?
C14 C15 H15A . . 119.9 ?
C16 C15 H15A . . 119.9 ?
C17 C16 C15 . . 119.94(8) ?
C17 C16 H16A . . 120.0 ?
C15 C16 H16A . . 120.0 ?
C16 C17 C12 . . 121.04(8) ?
C16 C17 H17A . . 119.5 ?
C12 C17 H17A . . 119.5 ?
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
C9 N2 N3 C10 . . . . 0.01(11) ?
C9 N4 N5 C11 . . . . -173.61(8) ?
C10 N4 N5 C11 . . . . 11.79(14) ?
C6 C1 C2 C3 . . . . -0.94(15) ?
C1 C2 C3 C4 . . . . -0.30(16) ?
C2 C3 C4 C5 . . . . 1.02(16) ?
C3 C4 C5 C6 . . . . -0.50(15) ?
C4 C5 C6 C1 . . . . -0.73(14) ?
C4 C5 C6 C7 . . . . -178.80(8) ?
C2 C1 C6 C5 . . . . 1.45(13) ?
C2 C1 C6 C7 . . . . 179.61(8) ?
C8 N1 C7 O1 . . . . 1.88(12) ?
C8 N1 C7 C6 . . . . -178.27(7) ?
C5 C6 C7 O1 . . . . 148.96(9) ?
C1 C6 C7 O1 . . . . -29.16(12) ?
C5 C6 C7 N1 . . . . -30.88(12) ?
C1 C6 C7 N1 . . . . 151.00(8) ?
C7 N1 C8 C9 . . . . -83.83(10) ?
N3 N2 C9 N4 . . . . 1.23(10) ?
N3 N2 C9 C8 . . . . -177.50(8) ?
N5 N4 C9 N2 . . . . -177.97(7) ?
C10 N4 C9 N2 . . . . -2.04(10) ?
N5 N4 C9 C8 . . . . 0.86(12) ?
C10 N4 C9 C8 . . . . 176.80(8) ?
N1 C8 C9 N2 . . . . 3.33(13) ?
N1 C8 C9 N4 . . . . -175.30(7) ?
N2 N3 C10 N4 . . . . -1.18(10) ?
N2 N3 C10 S1 . . . . 177.48(7) ?
C9 N4 C10 N3 . . . . 1.84(9) ?
N5 N4 C10 N3 . . . . 176.80(9) ?
C9 N4 C10 S1 . . . . -176.74(7) ?
N5 N4 C10 S1 . . . . -1.79(15) ?
N4 N5 C11 C12 . . . . -179.19(7) ?
N5 C11 C12 C13 . . . . -169.43(8) ?
N5 C11 C12 C17 . . . . 10.21(12) ?
C17 C12 C13 C14 . . . . -1.71(12) ?
C11 C12 C13 C14 . . . . 177.95(8) ?
C17 C12 C13 Cl1 . . . . 178.51(6) ?
C11 C12 C13 Cl1 . . . . -1.83(11) ?
C12 C13 C14 C15 . . . . 0.51(13) ?
Cl1 C13 C14 C15 . . . . -179.70(7) ?
C13 C14 C15 C16 . . . . 0.73(13) ?
C14 C15 C16 C17 . . . . -0.71(14) ?
C15 C16 C17 C12 . . . . -0.54(14) ?
C13 C12 C17 C16 . . . . 1.72(13) ?
C11 C12 C17 C16 . . . . -177.94(8) ?
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
N3 H1N3 O1 4_585 0.850(10)
1.890(10)
2.7362(10) 175.0(10)
N1 H1N1 O1 2_645 0.840(10)
2.290(10)
2.9450(10) 134(2)