##############################################################################
# #
# 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 Acta Crystallographica 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. #
# #
# Software is freely available for graphical display of the structure(s) #
# in this CIF. For information consult the CIF software page #
# http://www.iucr.org/resources/cif/software. #
# #
# This file may be used for bona fide research purposes within the #
# scientific community so long as proper attribution is given to the journal #
# article from which it was obtained. #
# #
##############################################################################
data_I
_audit_creation_method SHELXL-97
_journal_date_recd_electronic 2017-06-08
_journal_date_accepted 2017-06-12
_journal_name_full 'Acta Crystallographica, Section E'
_journal_year 2017
_journal_volume 73
_journal_issue 7
_journal_page_first 1041
_journal_page_last 1043
_journal_paper_category GO
_journal_paper_doi 10.1107/S2056989017008738
_journal_coeditor_code HG5489
_publ_contact_author_name 'Peter G. Jones'
_publ_contact_author_address
; Institut f\"ur Anorganische und Analytische Chemie
Technische Universit\"at Braunschweig
Postfach 3329
D-38023 Braunschweig
Germany
;
_publ_contact_author_email p.jones@tu-bs.de
_publ_contact_author_fax ?
_publ_contact_author_phone ?
_publ_section_title
;\
Crystal structure of
N'-[2-(benzo[d]thiazol-2-yl)acetyl]-4-\
methylbenzenesulfonohydrazide
;
loop_
_publ_author_name
_publ_author_address
'Azzam, Rasha A.'
; Chemistry Department
Faculty of Science
Helwan University
Cairo
Egypt
;
'Elgemeie, Galal H.'
; Chemistry Department
Faculty of Science
Helwan University
Cairo
Egypt
;
'Elsayed, Rasha E.'
; Chemistry Department
Faculty of Science
Helwan University
Cairo
Egypt
;
'Jones, Peter G.'
; Institut f\"ur Anorganische und Analytische Chemie
Technische Universit\"at Braunschweig
Postfach 3329
D-38023 Braunschweig
Germany
;
_publ_section_synopsis
;
In the title compound, the hydrazide N atom bonded to the C\\db O group is
planar, whereas that bonded to the SO~2~ group is pyramidally coordinated. The
interplanar angle between the ring systems is 40.71(3)\%. In the crystal,
molecules are connected by N---H...O\\db C and N---H...N~thiazole~ hydrogen
bonds, forming ribbons parallel to the b axis.
;
_chemical_name_systematic
;\
N'-[2-(Benzo[d]thiazol-2-yl)acetyl]-4-\
methylbenzenesulfonohydrazide
;
_chemical_name_common ?
_chemical_formula_moiety 'C16 H15 N3 O3 S2'
_chemical_formula_sum 'C16 H15 N3 O3 S2'
_chemical_formula_iupac 'C16 H15 N3 O3 S2'
_chemical_formula_weight 361.43
_chemical_melting_point ?
_symmetry_cell_setting triclinic
_symmetry_space_group_name_H-M 'P -1'
_symmetry_space_group_name_Hall '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.3436(4)
_cell_length_b 9.7591(5)
_cell_length_c 10.8815(6)
_cell_angle_alpha 97.905(4)
_cell_angle_beta 98.142(4)
_cell_angle_gamma 101.576(4)
_cell_volume 846.59(8)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 13640
_cell_measurement_theta_min 2.6290
_cell_measurement_theta_max 30.7750
_cell_measurement_temperature 100(2)
_exptl_crystal_description tablet
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.5
_exptl_crystal_size_mid 0.4
_exptl_crystal_size_min 0.2
_exptl_crystal_density_diffrn 1.418
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 376
_exptl_absorpt_coefficient_mu 0.334
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku Oxford Diffraction, 2015)
;
_exptl_absorpt_correction_T_min 0.95230
_exptl_absorpt_correction_T_max 1.00000
_exptl_special_details ?
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method \w-scan
_diffrn_detector_area_resol_mean 16.1419
_diffrn_reflns_number 45592
_diffrn_reflns_av_R_equivalents 0.0323
_diffrn_reflns_av_sigmaI/netI 0.0201
_diffrn_reflns_theta_min 2.53
_diffrn_reflns_theta_max 31.05
_diffrn_reflns_theta_full 30.00
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_limit_l_max 15
_diffrn_standards_number ?
_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^ > 2sigma(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 5040
_reflns_number_gt 4503
_reflns_threshold_expression >2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0361
_refine_ls_R_factor_gt 0.0308
_refine_ls_wR_factor_gt 0.0757
_refine_ls_wR_factor_ref 0.0791
_refine_ls_goodness_of_fit_ref 1.051
_refine_ls_restrained_S_all 1.051
_refine_ls_number_reflns 5040
_refine_ls_number_parameters 226
_refine_ls_number_restraints 0
_refine_ls_hydrogen_treatment mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0354P)^2^+0.3550P] 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 0.008
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.408
_refine_diff_density_min -0.417
_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'
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_molecular_graphics
;
XP (Siemens, 1994)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008)
;
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.57619(4) 0.26397(3) 0.86910(3) 0.01947(7) Uani d . 1 1 . .
C C2 0.56817(13) 0.15226(11) 0.72845(10) 0.01492(19) Uani d . 1 1 . .
N N3 0.46391(11) 0.03031(9) 0.70990(9) 0.01448(17) Uani d . 1 1 . .
C C3A 0.38014(13) 0.01774(11) 0.81106(10) 0.01466(19) Uani d . 1 1 . .
C C4 0.25456(14) -0.09823(12) 0.81811(11) 0.0185(2) Uani d . 1 1 . .
H H4 0.2221 -0.1782 0.7522 0.022 Uiso calc R 1 1 . .
C C5 0.17867(14) -0.09401(13) 0.92308(12) 0.0223(2) Uani d . 1 1 . .
H H5 0.0920 -0.1714 0.9287 0.027 Uiso calc R 1 1 . .
C C6 0.22767(15) 0.02293(14) 1.02157(11) 0.0238(2) Uani d . 1 1 . .
H H6 0.1749 0.0225 1.0934 0.029 Uiso calc R 1 1 . .
C C7 0.35125(15) 0.13868(13) 1.01602(11) 0.0223(2) Uani d . 1 1 . .
H H7 0.3840 0.2178 1.0827 0.027 Uiso calc R 1 1 . .
C C7A 0.42644(13) 0.13542(12) 0.90892(10) 0.0170(2) Uani d . 1 1 . .
C C8 0.66708(13) 0.20010(12) 0.63115(11) 0.0172(2) Uani d . 1 1 . .
H H8A 0.6814 0.1169 0.5740 0.021 Uiso calc R 1 1 . .
H H8B 0.7784 0.2573 0.6723 0.021 Uiso calc R 1 1 . .
C C9 0.57197(12) 0.28914(11) 0.55711(10) 0.01401(19) Uani d . 1 1 . .
N N1 0.50433(11) 0.22734(9) 0.43761(9) 0.01544(17) Uani d . 1 1 . .
H H01 0.519(2) 0.1475(18) 0.4007(15) 0.027(4) Uiso d . 1 1 . .
N N2 0.40574(11) 0.29335(10) 0.35950(9) 0.01529(17) Uani d . 1 1 . .
H H02 0.434(2) 0.3829(18) 0.3759(15) 0.029(4) Uiso d . 1 1 . .
O O1 0.12667(11) 0.31786(9) 0.27597(8) 0.02335(18) Uani d . 1 1 . .
S S2 0.20281(3) 0.23646(3) 0.35718(2) 0.01622(7) Uani d . 1 1 . .
O O2 0.16863(11) 0.08446(8) 0.32664(8) 0.02168(17) Uani d . 1 1 . .
O O3 0.55748(10) 0.40588(8) 0.60522(8) 0.01870(16) Uani d . 1 1 . .
C C11 0.16430(13) 0.28095(11) 0.51069(11) 0.0163(2) Uani d . 1 1 . .
C C12 0.15942(14) 0.42100(12) 0.55429(12) 0.0203(2) Uani d . 1 1 . .
H H12 0.1721 0.4901 0.5007 0.024 Uiso calc R 1 1 . .
C C13 0.13587(15) 0.45785(12) 0.67661(12) 0.0233(2) Uani d . 1 1 . .
H H13 0.1329 0.5532 0.7069 0.028 Uiso calc R 1 1 . .
C C14 0.11639(14) 0.35757(13) 0.75641(11) 0.0208(2) Uani d . 1 1 . .
C C15 0.11840(13) 0.21746(12) 0.71012(11) 0.0196(2) Uani d . 1 1 . .
H H15 0.1023 0.1477 0.7628 0.023 Uiso calc R 1 1 . .
C C16 0.14367(13) 0.17876(11) 0.58797(11) 0.0176(2) Uani d . 1 1 . .
H H16 0.1468 0.0835 0.5575 0.021 Uiso calc R 1 1 . .
C C17 0.09014(19) 0.39948(16) 0.88922(13) 0.0327(3) Uani d . 1 1 . .
H H17A 0.0428 0.4838 0.8946 0.049 Uiso calc PR 0.50 1 . .
H H17B 0.1969 0.4207 0.9468 0.049 Uiso calc PR 0.50 1 . .
H H17C 0.0137 0.3212 0.9127 0.049 Uiso calc PR 0.50 1 . .
H H17D 0.1261 0.3334 0.9415 0.049 Uiso calc PR 0.50 1 . .
H H17E -0.0280 0.3964 0.8893 0.049 Uiso calc PR 0.50 1 . .
H H17F 0.1552 0.4960 0.9233 0.049 Uiso calc PR 0.50 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
S1 0.02314(14) 0.01447(12) 0.01758(14) 0.00166(10) 0.00006(10) -0.00091(9)
C2 0.0156(4) 0.0138(4) 0.0160(5) 0.0062(4) 0.0003(4) 0.0028(4)
N3 0.0162(4) 0.0134(4) 0.0152(4) 0.0061(3) 0.0028(3) 0.0029(3)
C3A 0.0154(4) 0.0149(4) 0.0144(5) 0.0061(4) 0.0009(4) 0.0027(4)
C4 0.0177(5) 0.0180(5) 0.0193(5) 0.0038(4) 0.0019(4) 0.0039(4)
C5 0.0174(5) 0.0285(6) 0.0225(6) 0.0043(4) 0.0042(4) 0.0101(5)
C6 0.0215(5) 0.0366(7) 0.0168(5) 0.0109(5) 0.0054(4) 0.0074(5)
C7 0.0249(6) 0.0279(6) 0.0144(5) 0.0104(5) 0.0017(4) 0.0003(4)
C7A 0.0178(5) 0.0173(5) 0.0155(5) 0.0053(4) 0.0003(4) 0.0016(4)
C8 0.0150(5) 0.0175(5) 0.0207(5) 0.0054(4) 0.0028(4) 0.0064(4)
C9 0.0130(4) 0.0125(4) 0.0169(5) 0.0018(3) 0.0033(4) 0.0043(4)
N1 0.0184(4) 0.0119(4) 0.0170(4) 0.0071(3) 0.0025(3) 0.0012(3)
N2 0.0186(4) 0.0122(4) 0.0155(4) 0.0053(3) 0.0018(3) 0.0020(3)
O1 0.0244(4) 0.0237(4) 0.0210(4) 0.0090(3) -0.0038(3) 0.0031(3)
S2 0.01722(12) 0.01375(12) 0.01595(13) 0.00428(9) -0.00088(9) -0.00068(9)
O2 0.0247(4) 0.0139(4) 0.0223(4) 0.0018(3) 0.0004(3) -0.0036(3)
O3 0.0264(4) 0.0110(3) 0.0175(4) 0.0041(3) 0.0012(3) 0.0010(3)
C11 0.0134(4) 0.0156(5) 0.0194(5) 0.0047(4) 0.0020(4) -0.0002(4)
C12 0.0219(5) 0.0151(5) 0.0258(6) 0.0065(4) 0.0074(4) 0.0030(4)
C13 0.0247(6) 0.0163(5) 0.0298(6) 0.0070(4) 0.0101(5) -0.0014(4)
C14 0.0162(5) 0.0230(5) 0.0235(6) 0.0056(4) 0.0060(4) -0.0001(4)
C15 0.0159(5) 0.0206(5) 0.0229(6) 0.0053(4) 0.0031(4) 0.0049(4)
C16 0.0149(5) 0.0142(5) 0.0228(5) 0.0046(4) 0.0006(4) 0.0007(4)
C17 0.0379(7) 0.0349(7) 0.0264(7) 0.0088(6) 0.0143(6) -0.0010(5)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
Least-squares planes (x,y,z in crystal coordinates) and deviations from them
(* indicates atom used to define plane)
6.2088 (0.0012) x - 6.2111 (0.0022) y + 4.5043 (0.0028) z = 5.8783 (0.0023)
* -0.0257 (0.0005) S1
* -0.0152 (0.0007) C2
* 0.0114 (0.0007) N3
* 0.0250 (0.0009) C3A
* -0.0026 (0.0008) C4
* -0.0272 (0.0009) C5
* -0.0057 (0.0009) C6
* 0.0176 (0.0009) C7
* 0.0223 (0.0009) C7A
Rms deviation of fitted atoms = 0.0190
7.8014 (0.0014) x - 0.3099 (0.0046) y + 1.6293 (0.0049) z = 2.0216 (0.0030)
Angle to previous plane (with approximate esd) = 40.71 ( 0.03 )
* 0.0051 (0.0008) C11
* -0.0053 (0.0008) C12
* -0.0012 (0.0008) C13
* 0.0080 (0.0008) C14
* -0.0083 (0.0008) C15
* 0.0018 (0.0008) C16
Rms deviation of fitted atoms = 0.0057
===========================================================
Least-squares planes (x,y,z in crystal coordinates) and deviations from them
(* indicates atom used to define plane)
6.5691 (0.0357) x + 3.5739 (0.0897) y - 5.4501 (0.0327) z = 1.7544 (0.0236)
* 0.0000 (0.0001) C9
* 0.0000 (0.0000) H01
* 0.0000 (0.0000) N2
-0.0139 (0.0071) N1
Rms deviation of fitted atoms = 0.0000
- 2.5491 (0.0143) x + 2.7622 (0.0942) y + 9.8695 (0.0419) z = 3.6614 (0.0102)
Angle to previous plane (with approximate esd) = 66.25 ( 0.42 )
* 0.0000 (0.0000) S2
* 0.0000 (0.0000) H02
* 0.0000 (0.0000) N1
-0.3372 (0.0082) N2
Rms deviation of fitted atoms = 0.0000
;
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 C7A . 1.7310(12) ?
S1 C2 . 1.7373(11) y
C2 N3 . 1.2972(14) y
C2 C8 . 1.4996(15) ?
N3 C3A . 1.3914(14) ?
C3A C4 . 1.3983(15) ?
C3A C7A . 1.4040(15) ?
C4 C5 . 1.3819(16) ?
C5 C6 . 1.4037(18) ?
C6 C7 . 1.3826(18) ?
C7 C7A . 1.3992(16) ?
C8 C9 . 1.5238(14) ?
C9 O3 . 1.2231(13) ?
C9 N1 . 1.3464(14) ?
N1 N2 . 1.4069(12) y
N2 S2 . 1.6680(10) ?
O1 S2 . 1.4325(8) ?
S2 O2 . 1.4353(8) ?
S2 C11 . 1.7580(11) ?
C11 C16 . 1.3907(16) ?
C11 C12 . 1.3944(15) ?
C12 C13 . 1.3821(17) ?
C13 C14 . 1.3957(18) ?
C14 C15 . 1.3949(16) ?
C14 C17 . 1.5056(17) ?
C15 C16 . 1.3882(16) ?
C4 H4 . 0.9500 ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
N1 H01 . 0.866(16) ?
N2 H02 . 0.845(17) ?
C12 H12 . 0.9500 ?
C13 H13 . 0.9500 ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
C17 H17D . 0.9800 ?
C17 H17E . 0.9800 ?
C17 H17F . 0.9800 ?
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
C7A S1 C2 . . 89.39(5) y
N3 C2 C8 . . 122.61(10) ?
N3 C2 S1 . . 115.98(8) ?
C8 C2 S1 . . 121.25(8) ?
C2 N3 C3A . . 110.63(9) ?
N3 C3A C4 . . 124.96(10) ?
N3 C3A C7A . . 114.86(10) ?
C4 C3A C7A . . 120.15(10) ?
C5 C4 C3A . . 118.54(11) ?
C4 C5 C6 . . 120.98(11) ?
C7 C6 C5 . . 121.26(11) ?
C6 C7 C7A . . 117.79(11) ?
C7 C7A C3A . . 121.26(11) ?
C7 C7A S1 . . 129.57(9) ?
C3A C7A S1 . . 109.14(8) ?
C2 C8 C9 . . 107.51(8) ?
O3 C9 N1 . . 123.90(10) ?
O3 C9 C8 . . 121.56(10) ?
N1 C9 C8 . . 114.53(9) ?
C9 N1 N2 . . 121.14(9) y
N1 N2 S2 . . 112.94(7) y
O1 S2 O2 . . 120.92(5) ?
O1 S2 N2 . . 103.98(5) ?
O2 S2 N2 . . 106.20(5) ?
O1 S2 C11 . . 109.49(5) ?
O2 S2 C11 . . 107.66(5) ?
N2 S2 C11 . . 107.89(5) ?
C16 C11 C12 . . 120.86(10) ?
C16 C11 S2 . . 120.35(8) ?
C12 C11 S2 . . 118.76(9) ?
C13 C12 C11 . . 119.02(11) ?
C12 C13 C14 . . 121.22(10) ?
C15 C14 C13 . . 118.82(11) ?
C15 C14 C17 . . 120.67(12) ?
C13 C14 C17 . . 120.50(11) ?
C16 C15 C14 . . 120.77(11) ?
C15 C16 C11 . . 119.28(10) ?
C5 C4 H4 . . 120.7 ?
C3A C4 H4 . . 120.7 ?
C4 C5 H5 . . 119.5 ?
C6 C5 H5 . . 119.5 ?
C7 C6 H6 . . 119.4 ?
C5 C6 H6 . . 119.4 ?
C6 C7 H7 . . 121.1 ?
C7A C7 H7 . . 121.1 ?
C2 C8 H8A . . 110.2 ?
C9 C8 H8A . . 110.2 ?
C2 C8 H8B . . 110.2 ?
C9 C8 H8B . . 110.2 ?
H8A C8 H8B . . 108.5 ?
C9 N1 H01 . . 124.9(11) ?
N2 N1 H01 . . 113.9(11) ?
N1 N2 H02 . . 113.1(11) ?
S2 N2 H02 . . 111.0(11) ?
C13 C12 H12 . . 120.5 ?
C11 C12 H12 . . 120.5 ?
C12 C13 H13 . . 119.4 ?
C14 C13 H13 . . 119.4 ?
C16 C15 H15 . . 119.6 ?
C14 C15 H15 . . 119.6 ?
C15 C16 H16 . . 120.4 ?
C11 C16 H16 . . 120.4 ?
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 C17 H17D . . 109.5 ?
H17A C17 H17D . . 141.1 ?
H17B C17 H17D . . 56.3 ?
H17C C17 H17D . . 56.3 ?
C14 C17 H17E . . 109.5 ?
H17A C17 H17E . . 56.3 ?
H17B C17 H17E . . 141.1 ?
H17C C17 H17E . . 56.3 ?
H17D C17 H17E . . 109.5 ?
C14 C17 H17F . . 109.5 ?
H17A C17 H17F . . 56.3 ?
H17B C17 H17F . . 56.3 ?
H17C C17 H17F . . 141.1 ?
H17D C17 H17F . . 109.5 ?
H17E C17 H17F . . 109.5 ?
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
C7A S1 C2 N3 . . . . 0.45(8) ?
C7A S1 C2 C8 . . . . 175.95(9) ?
C8 C2 N3 C3A . . . . -175.40(9) ?
S1 C2 N3 C3A . . . . 0.03(11) ?
C2 N3 C3A C4 . . . . 177.18(10) ?
C2 N3 C3A C7A . . . . -0.66(13) ?
N3 C3A C4 C5 . . . . -177.98(10) ?
C7A C3A C4 C5 . . . . -0.24(16) ?
C3A C4 C5 C6 . . . . -0.91(17) ?
C4 C5 C6 C7 . . . . 1.12(18) ?
C5 C6 C7 C7A . . . . -0.15(17) ?
C6 C7 C7A C3A . . . . -1.00(16) ?
C6 C7 C7A S1 . . . . 176.79(9) ?
N3 C3A C7A C7 . . . . 179.17(10) ?
C4 C3A C7A C7 . . . . 1.22(16) ?
N3 C3A C7A S1 . . . . 0.98(11) ?
C4 C3A C7A S1 . . . . -176.98(8) ?
C2 S1 C7A C7 . . . . -178.77(11) ?
C2 S1 C7A C3A . . . . -0.76(8) ?
N3 C2 C8 C9 . . . . 94.63(11) ?
S1 C2 C8 C9 . . . . -80.57(10) y
C2 C8 C9 O3 . . . . 68.95(13) ?
C2 C8 C9 N1 . . . . -109.79(10) y
O3 C9 N1 N2 . . . . -1.96(16) ?
C8 C9 N1 N2 . . . . 176.74(9) y
C9 N1 N2 S2 . . . . -96.08(10) y
N1 N2 S2 O1 . . . . 178.74(7) ?
N1 N2 S2 O2 . . . . -52.67(8) ?
N1 N2 S2 C11 . . . . 62.53(8) y
O1 S2 C11 C16 . . . . 146.33(9) ?
O2 S2 C11 C16 . . . . 13.11(10) ?
N2 S2 C11 C16 . . . . -101.12(9) ?
O1 S2 C11 C12 . . . . -35.40(10) ?
O2 S2 C11 C12 . . . . -168.61(9) ?
N2 S2 C11 C12 . . . . 77.16(9) y
C16 C11 C12 C13 . . . . 0.85(17) ?
S2 C11 C12 C13 . . . . -177.42(9) ?
C11 C12 C13 C14 . . . . -0.25(18) ?
C12 C13 C14 C15 . . . . -1.00(18) ?
C12 C13 C14 C17 . . . . -179.74(12) ?
C13 C14 C15 C16 . . . . 1.68(17) ?
C17 C14 C15 C16 . . . . -179.58(11) ?
C14 C15 C16 C11 . . . . -1.10(16) ?
C12 C11 C16 C15 . . . . -0.18(16) ?
S2 C11 C16 C15 . . . . 178.06(8) ?
H01 N1 N2 H02 . . . . -146.7(17) y
O3 C9 N1 H01 . . . . 175.5(13) y
H02 N2 S2 O2 . . . . 179.1(12) y
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
N1 H01 N3 2_656 0.866(16) 2.013(16) 2.8717(13) 171.0(15)
N2 H02 O3 2_666 0.845(17) 2.029(17) 2.8553(12) 165.7(16)
C6 H6 O2 1_556 0.95 2.54 3.4142(15) 153.6
_iucr_refine_instructions_details
;
TITL elg_bst in P-1
CELL 0.71073 8.343582 9.759095 10.881473 97.9047 98.1415 101.5760
ZERR 2.00 0.0004 0.0005 0.0006 0.004 0.004 0.004
LATT 1
SFAC C H N O S
UNIT 32.00 30.00 6.00 6.00 4.00
TEMP -173
SIZE 0.5 0.4 0.2
FMAP 2
PLAN 10
L.S. 4
ACTA 60
CONF
EQIV $1 -x+1, -y, -z+1
EQIV $2 -x+1, -y+1, -z+1
HTAB N1 N3_$1
HTAB N2 O3_$2
WGHT 0.035400 0.355000
FVAR 7.50020
S1 5 0.576189 0.263966 0.869100 11.00000 0.02314 0.01447 =
0.01758 -0.00091 0.00006 0.00166
C2 1 0.568174 0.152263 0.728450 11.00000 0.01563 0.01377 =
0.01597 0.00282 0.00034 0.00621
N3 3 0.463913 0.030306 0.709898 11.00000 0.01621 0.01339 =
0.01517 0.00286 0.00276 0.00613
C3A 1 0.380140 0.017737 0.811056 11.00000 0.01535 0.01494 =
0.01441 0.00275 0.00092 0.00609
C4 1 0.254562 -0.098231 0.818112 11.00000 0.01772 0.01803 =
0.01935 0.00395 0.00193 0.00380
AFIX 43
H4 2 0.222136 -0.178156 0.752198 11.00000 -1.20000
AFIX 0
C5 1 0.178666 -0.094014 0.923076 11.00000 0.01740 0.02854 =
0.02246 0.01013 0.00416 0.00427
AFIX 43
H5 2 0.092042 -0.171405 0.928663 11.00000 -1.20000
AFIX 0
C6 1 0.227675 0.022933 1.021566 11.00000 0.02150 0.03659 =
0.01676 0.00737 0.00541 0.01093
AFIX 43
H6 2 0.174925 0.022540 1.093410 11.00000 -1.20000
AFIX 0
C7 1 0.351248 0.138684 1.016016 11.00000 0.02487 0.02790 =
0.01445 0.00029 0.00172 0.01039
AFIX 43
H7 2 0.384011 0.217802 1.082706 11.00000 -1.20000
AFIX 0
C7A 1 0.426440 0.135424 0.908917 11.00000 0.01779 0.01731 =
0.01551 0.00164 0.00035 0.00531
C8 1 0.667085 0.200101 0.631150 11.00000 0.01500 0.01745 =
0.02066 0.00641 0.00285 0.00541
AFIX 23
H8A 2 0.681378 0.116940 0.574048 11.00000 -1.20000
H8B 2 0.778392 0.257309 0.672311 11.00000 -1.20000
AFIX 0
C9 1 0.571969 0.289135 0.557109 11.00000 0.01299 0.01249 =
0.01685 0.00430 0.00333 0.00183
N1 3 0.504334 0.227338 0.437612 11.00000 0.01844 0.01188 =
0.01703 0.00116 0.00245 0.00711
H01 2 0.519237 0.147513 0.400680 11.00000 0.02687
N2 3 0.405736 0.293346 0.359503 11.00000 0.01856 0.01217 =
0.01550 0.00199 0.00180 0.00535
H02 2 0.433947 0.382884 0.375900 11.00000 0.02915
O1 4 0.126670 0.317856 0.275968 11.00000 0.02438 0.02370 =
0.02097 0.00309 -0.00382 0.00902
S2 5 0.202813 0.236464 0.357181 11.00000 0.01722 0.01375 =
0.01595 -0.00068 -0.00088 0.00428
O2 4 0.168627 0.084458 0.326636 11.00000 0.02467 0.01394 =
0.02226 -0.00364 0.00037 0.00178
O3 4 0.557479 0.405882 0.605219 11.00000 0.02636 0.01095 =
0.01755 0.00099 0.00124 0.00413
C11 1 0.164300 0.280951 0.510694 11.00000 0.01344 0.01560 =
0.01942 -0.00018 0.00198 0.00465
C12 1 0.159418 0.421005 0.554290 11.00000 0.02187 0.01514 =
0.02581 0.00298 0.00740 0.00646
AFIX 43
H12 2 0.172092 0.490078 0.500708 11.00000 -1.20000
AFIX 0
C13 1 0.135867 0.457851 0.676608 11.00000 0.02469 0.01629 =
0.02982 -0.00142 0.01006 0.00696
AFIX 43
H13 2 0.132878 0.553198 0.706928 11.00000 -1.20000
AFIX 0
C14 1 0.116395 0.357573 0.756409 11.00000 0.01615 0.02299 =
0.02347 -0.00008 0.00597 0.00559
C15 1 0.118401 0.217461 0.710120 11.00000 0.01589 0.02062 =
0.02293 0.00491 0.00307 0.00532
AFIX 43
H15 2 0.102288 0.147712 0.762804 11.00000 -1.20000
AFIX 0
C16 1 0.143669 0.178757 0.587970 11.00000 0.01493 0.01424 =
0.02278 0.00068 0.00063 0.00459
AFIX 43
H16 2 0.146833 0.083495 0.557495 11.00000 -1.20000
AFIX 0
C17 1 0.090140 0.399483 0.889219 11.00000 0.03790 0.03490 =
0.02642 -0.00104 0.01433 0.00885
AFIX 127
H17A 2 0.042776 0.483793 0.894577 10.50000 -1.50000
H17B 2 0.196857 0.420732 0.946786 10.50000 -1.50000
H17C 2 0.013698 0.321201 0.912741 10.50000 -1.50000
H17D 2 0.126112 0.333358 0.941493 10.50000 -1.50000
H17E 2 -0.027970 0.396419 0.889283 10.50000 -1.50000
H17F 2 0.155189 0.495950 0.923328 10.50000 -1.50000
HKLF 4
;