# Supplementary Material (ESI) for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2010
data_global
_journal_name_full CrystEngComm
_journal_coden_Cambridge 1350
_publ_contact_author_name 'Janiak, Christoph'
_publ_contact_author_email janiak@uni-freiburg.de
_publ_section_title
;
Can a small amount of crystal solvent be overlooked
or have no structural effect? Isomorphous non-stoichiometric
solvates (pseudo-polymorphs): The case of
salicylaldehyde thiosemicarbazone
;
loop_
_publ_author_name
H.Hosseini-Monfared
A.-C.Chamayou
S.Khajeh
C.Janiak
#===END
data_sk-64
_database_code_depnum_ccdc_archive 'CCDC 692824'
#TrackingRef '- 1-xH2Ocrystaldata.CIF'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
Salicylaldehyde thiosemicarbazone 0.17hydrate;
(E)-2-(2-hydroxybenzylidene)hydrazinecarbothioamide 0.17hydrate
;
_chemical_name_common
;
Salicylaldehyde thiosemicarbazone 0.17hydrate; (E)-2-(2-
hydroxybenzylidene)hydrazinecarbothioamide 0.17hydrate
;
_chemical_melting_point ?
_chemical_formula_moiety 'C8 H9 N3 O S, 0.17(H2 O)'
_chemical_formula_sum 'C8 H9.34 N3 O1.17 S'
_chemical_formula_weight 198.31
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'
O O 0.0106 0.0060 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'C 2/c'
_symmetry_space_group_name_Hall '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a 13.7595(6)
_cell_length_b 14.2594(6)
_cell_length_c 10.4876(4)
_cell_angle_alpha 90.00
_cell_angle_beta 115.3670(10)
_cell_angle_gamma 90.00
_cell_volume 1859.29(13)
_cell_formula_units_Z 8
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 4993
_cell_measurement_theta_min 2.17
_cell_measurement_theta_max 33.44
_exptl_crystal_description plate
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.45
_exptl_crystal_size_mid 0.35
_exptl_crystal_size_min 0.30
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.417
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 830
_exptl_absorpt_coefficient_mu 0.313
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.8721
_exptl_absorpt_correction_T_max 0.9120
_exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker SMART APEXII CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 9341
_diffrn_reflns_av_R_equivalents 0.0179
_diffrn_reflns_av_sigmaI/netI 0.0128
_diffrn_reflns_limit_h_min -17
_diffrn_reflns_limit_h_max 17
_diffrn_reflns_limit_k_min -17
_diffrn_reflns_limit_k_max 17
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_theta_min 2.17
_diffrn_reflns_theta_max 26.59
_reflns_number_total 1952
_reflns_number_gt 1762
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'APEX2 (Bruker, 2006)'
_computing_cell_refinement 'SAINT (Bruker, 2006)'
_computing_data_reduction SAINT
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'DIAMOND (Crystal Impact, 2009)'
_computing_publication_material ?
_publ_section_references
;
Bruker (2006). APEX2 (Version 2.1-0) and SAINT.
Bruker Analytical X-ray Systems, Madison, Wisconsin, USA.
Crystal Impact (2009). DIAMOND. Version 3.2d. Crystal Impact GbR, Bonn,
Germany.
Sheldrick, G. M. (1996). SADABS. University of G\"ottingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122.
;
_publ_section_exptl_refinement
;
Hydrogen atoms for aromatic CH were positioned geometrically
(C---H = 0.94 \%A) and refined
using a riding model, with U~iso~(H) = 1.2U~eq~(CH).
H atoms on the hydroxy and partly occupied crystal water oxygen atom,
on the amine and on the hydrazone nitrogen atom were found and
refined with U~iso~(H) = 1.5U~eq~(O,N).
;
_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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0389P)^2^+1.6872P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 1952
_refine_ls_number_parameters 139
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0385
_refine_ls_R_factor_gt 0.0341
_refine_ls_wR_factor_ref 0.0888
_refine_ls_wR_factor_gt 0.0857
_refine_ls_goodness_of_fit_ref 1.066
_refine_ls_restrained_S_all 1.066
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
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
S S 0.20444(4) 0.39214(3) -0.07857(5) 0.04949(17) Uani 1 1 d . . .
O1 O 0.09598(9) 0.36110(8) 0.43736(12) 0.0364(3) Uani 1 1 d . . .
H1 H 0.1139(16) 0.3653(15) 0.366(2) 0.055 Uiso 1 1 d . . .
N1 N 0.15026(9) 0.29969(9) 0.23700(12) 0.0285(3) Uani 1 1 d . . .
N2 N 0.17713(10) 0.30651(9) 0.12519(13) 0.0314(3) Uani 1 1 d . . .
H2N H 0.2031(15) 0.2571(15) 0.101(2) 0.047 Uiso 1 1 d . . .
N3 N 0.13686(13) 0.46353(11) 0.10242(16) 0.0441(4) Uani 1 1 d . . .
H3A H 0.1182(18) 0.4602(16) 0.169(2) 0.066 Uiso 1 1 d . . .
H3B H 0.1271(18) 0.5167(17) 0.058(2) 0.066 Uiso 1 1 d . . .
C1 C 0.17008(12) 0.38850(11) 0.05855(16) 0.0334(3) Uani 1 1 d . . .
C2 C 0.15193(11) 0.21667(10) 0.28495(14) 0.0288(3) Uani 1 1 d . . .
H2 H 0.1706 0.1656 0.2416 0.035 Uiso 1 1 calc R . .
C3 C 0.12624(10) 0.19806(10) 0.40344(14) 0.0282(3) Uani 1 1 d . . .
C4 C 0.12980(12) 0.10557(11) 0.44972(16) 0.0339(3) Uani 1 1 d . . .
H4 H 0.1479 0.0565 0.4025 0.041 Uiso 1 1 calc R . .
C5 C 0.10736(13) 0.08417(12) 0.56310(17) 0.0398(4) Uani 1 1 d . . .
H5 H 0.1104 0.0211 0.5937 0.048 Uiso 1 1 calc R . .
C6 C 0.08039(13) 0.15594(13) 0.63147(17) 0.0409(4) Uani 1 1 d . . .
H6 H 0.0649 0.1416 0.7093 0.049 Uiso 1 1 calc R . .
C7 C 0.07572(12) 0.24811(12) 0.58801(16) 0.0371(4) Uani 1 1 d . . .
H7 H 0.0565 0.2965 0.6352 0.045 Uiso 1 1 calc R . .
C8 C 0.09927(11) 0.26957(11) 0.47475(15) 0.0299(3) Uani 1 1 d . . .
O2 O 0.0000 0.5106(3) 0.2500 0.0314(15) Uani 0.340(7) 2 d SP . .
H2A H -0.054(5) 0.546(4) 0.201(6) 0.047 Uiso 0.340(7) 1 d P . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S 0.0862(4) 0.0347(2) 0.0534(3) -0.00864(18) 0.0546(3) -0.0119(2)
O1 0.0430(6) 0.0340(6) 0.0403(6) -0.0062(5) 0.0256(5) -0.0013(5)
N1 0.0283(6) 0.0346(6) 0.0241(5) -0.0021(5) 0.0127(5) -0.0002(5)
N2 0.0383(7) 0.0333(7) 0.0287(6) -0.0039(5) 0.0202(5) -0.0007(5)
N3 0.0666(10) 0.0390(8) 0.0436(8) 0.0098(6) 0.0398(8) 0.0135(7)
C1 0.0364(7) 0.0359(8) 0.0316(7) -0.0040(6) 0.0182(6) -0.0047(6)
C2 0.0285(7) 0.0313(7) 0.0271(7) -0.0053(5) 0.0125(6) -0.0013(5)
C3 0.0229(6) 0.0351(7) 0.0253(6) -0.0028(5) 0.0090(5) -0.0023(5)
C4 0.0316(7) 0.0364(8) 0.0332(7) -0.0001(6) 0.0133(6) -0.0009(6)
C5 0.0362(8) 0.0443(9) 0.0413(9) 0.0082(7) 0.0187(7) -0.0025(7)
C6 0.0331(8) 0.0598(11) 0.0363(8) 0.0059(7) 0.0212(7) -0.0014(7)
C7 0.0304(7) 0.0513(9) 0.0343(8) -0.0052(7) 0.0184(6) -0.0007(6)
C8 0.0234(6) 0.0369(8) 0.0293(7) -0.0040(6) 0.0112(5) -0.0026(5)
O2 0.037(3) 0.030(2) 0.032(2) 0.000 0.019(2) 0.000
_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.
;
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
S C1 1.6961(15) . ?
O1 C8 1.3580(19) . ?
O1 H1 0.89(2) . ?
N1 C2 1.2825(19) . ?
N1 N2 1.3757(17) . ?
N2 C1 1.344(2) . ?
N2 H2N 0.87(2) . ?
N3 C1 1.321(2) . ?
N3 H3A 0.85(2) . ?
N3 H3B 0.87(2) . ?
C2 C3 1.4546(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.399(2) . ?
C3 C8 1.405(2) . ?
C4 C5 1.384(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.383(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.393(2) . ?
C7 H7 0.9500 . ?
O2 H2A 0.86(7) . ?
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
C8 O1 H1 108.8(14) . . ?
C2 N1 N2 115.67(12) . . ?
C1 N2 N1 121.26(12) . . ?
C1 N2 H2N 120.0(13) . . ?
N1 N2 H2N 118.6(13) . . ?
C1 N3 H3A 121.2(16) . . ?
C1 N3 H3B 121.0(15) . . ?
H3A N3 H3B 118(2) . . ?
N3 C1 N2 118.81(14) . . ?
N3 C1 S 122.29(12) . . ?
N2 C1 S 118.90(11) . . ?
N1 C2 C3 122.23(13) . . ?
N1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C4 C3 C8 118.51(13) . . ?
C4 C3 C2 118.90(13) . . ?
C8 C3 C2 122.58(13) . . ?
C5 C4 C3 121.22(15) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 119.24(16) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C7 C6 C5 121.01(14) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 119.66(15) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
O1 C8 C7 117.80(13) . . ?
O1 C8 C3 121.84(13) . . ?
C7 C8 C3 120.36(14) . . ?
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
C2 N1 N2 C1 174.65(13) . . . . ?
N1 N2 C1 N3 0.2(2) . . . . ?
N1 N2 C1 S 180.00(10) . . . . ?
N2 N1 C2 C3 179.55(12) . . . . ?
N1 C2 C3 C4 179.98(13) . . . . ?
N1 C2 C3 C8 -0.9(2) . . . . ?
C8 C3 C4 C5 0.0(2) . . . . ?
C2 C3 C4 C5 179.20(14) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C4 C5 C6 C7 0.0(2) . . . . ?
C5 C6 C7 C8 -0.6(2) . . . . ?
C6 C7 C8 O1 -178.62(13) . . . . ?
C6 C7 C8 C3 0.9(2) . . . . ?
C4 C3 C8 O1 178.87(13) . . . . ?
C2 C3 C8 O1 -0.3(2) . . . . ?
C4 C3 C8 C7 -0.6(2) . . . . ?
C2 C3 C8 C7 -179.75(13) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.89(2) 1.88(2) 2.6617(15) 146.3(19) .
N2 H2N S 0.87(2) 2.54(2) 3.4061(14) 169.9(17) 7
N3 H3A O2 0.85(2) 2.25(2) 2.9815(17) 145(2) .
N3 H3B O1 0.87(2) 2.09(3) 2.9549(18) 176(2) 6_565
O2 H2A S 0.86(7) 2.11(7) 2.956(2) 168(5) 5_565
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 26.59
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max 0.388
_refine_diff_density_min -0.428
_refine_diff_density_rms 0.042
# Attachment '- 1-xH2Ocrystaldata.CIF'
data_sk64_2fr
_database_code_depnum_ccdc_archive 'CCDC 771708'
#TrackingRef '- 1-xH2Ocrystaldata.CIF'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
Salicylaldehyde thiosemicarbazone 0.17hydrate;
(E)-2-(2-hydroxybenzylidene)hydrazinecarbothioamide 0.095hydrate
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C8 H9 N3 O S, 0.095(H2 O)'
_chemical_formula_sum 'C8 H9.19 N3 O1.10 S'
_chemical_formula_weight 196.95
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'
O O 0.0106 0.0060 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'C 2/c'
_symmetry_space_group_name_Hall '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a 13.9737(4)
_cell_length_b 14.2331(4)
_cell_length_c 10.4655(2)
_cell_angle_alpha 90.00
_cell_angle_beta 115.781(2)
_cell_angle_gamma 90.00
_cell_volume 1874.29(8)
_cell_formula_units_Z 8
_cell_measurement_temperature 203(2)
_cell_measurement_reflns_used 1464
_cell_measurement_theta_min 2.51
_cell_measurement_theta_max 25.38
_exptl_crystal_description plate
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.31
_exptl_crystal_size_mid 0.11
_exptl_crystal_size_min 0.04
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.396
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 824
_exptl_absorpt_coefficient_mu 0.309
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9089
_exptl_absorpt_correction_T_max 0.9884
_exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 203(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker APEXII CCD area detector'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 10068
_diffrn_reflns_av_R_equivalents 0.0372
_diffrn_reflns_av_sigmaI/netI 0.0257
_diffrn_reflns_limit_h_min -17
_diffrn_reflns_limit_h_max 17
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 17
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_theta_min 2.16
_diffrn_reflns_theta_max 26.59
_reflns_number_total 1968
_reflns_number_gt 1495
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'APEX2 (Bruker, 2006)'
_computing_cell_refinement 'SAINT (Bruker, 2006)'
_computing_data_reduction SAINT
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'DIAMOND (Crystal Impact, 2009)'
_computing_publication_material ?
_publ_section_references
;
Bruker (2006). APEX2 (Version 2.1-0) and SAINT.
Bruker Analytical X-ray Systems, Madison, Wisconsin, USA.
Crystal Impact (2009). DIAMOND. Version 3.2d. Crystal Impact GbR, Bonn,
Germany.
Sheldrick, G. M. (1996). SADABS. University of G\"ottingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122.
;
_publ_section_exptl_refinement
;
Hydrogen atoms for aromatic CH were positioned geometrically
(C---H = 0.94 \%A) and refined
using a riding model, with U~iso~(H) = 1.2U~eq~(CH).
H atoms on the hydroxy and partly occupied crystal water oxygen atom,
on the amine and on the hydrazone nitrogen atom were found and
refined with U~iso~(H) = 1.5U~eq~(O,N).
;
_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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0416P)^2^+1.4139P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 1968
_refine_ls_number_parameters 139
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0568
_refine_ls_R_factor_gt 0.0391
_refine_ls_wR_factor_ref 0.1028
_refine_ls_wR_factor_gt 0.0932
_refine_ls_goodness_of_fit_ref 1.058
_refine_ls_restrained_S_all 1.057
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
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
S S 0.20175(6) 0.39292(4) -0.08238(6) 0.0591(2) Uani 1 1 d . . .
O1 O 0.09598(12) 0.36155(10) 0.43341(16) 0.0468(4) Uani 1 1 d . . .
H1 H 0.115(2) 0.3640(18) 0.364(3) 0.070 Uiso 1 1 d . . .
N1 N 0.15175(11) 0.29988(11) 0.23577(15) 0.0336(4) Uani 1 1 d . . .
N2 N 0.17861(13) 0.30685(12) 0.12369(16) 0.0378(4) Uani 1 1 d . . .
H2N H 0.2063(17) 0.2558(17) 0.101(2) 0.057 Uiso 1 1 d . . .
N3 N 0.13775(18) 0.46354(14) 0.1011(2) 0.0557(5) Uani 1 1 d . . .
H3A H 0.121(2) 0.460(2) 0.171(3) 0.083 Uiso 1 1 d . . .
H3B H 0.126(2) 0.516(2) 0.055(3) 0.083 Uiso 1 1 d . . .
C1 C 0.17050(16) 0.38902(14) 0.0564(2) 0.0390(4) Uani 1 1 d . . .
C2 C 0.15307(14) 0.21682(13) 0.28382(18) 0.0339(4) Uani 1 1 d . . .
H2 H 0.1717 0.1661 0.2416 0.041 Uiso 1 1 calc R . .
C3 C 0.12677(13) 0.19844(13) 0.40141(18) 0.0332(4) Uani 1 1 d . . .
C4 C 0.12969(16) 0.10595(15) 0.4475(2) 0.0435(5) Uani 1 1 d . . .
H4 H 0.1481 0.0573 0.4016 0.052 Uiso 1 1 calc R . .
C5 C 0.10606(17) 0.08466(18) 0.5593(2) 0.0543(6) Uani 1 1 d . . .
H5 H 0.1089 0.0222 0.5899 0.065 Uiso 1 1 calc R . .
C6 C 0.07810(17) 0.15630(19) 0.6259(2) 0.0545(6) Uani 1 1 d . . .
H6 H 0.0615 0.1420 0.7016 0.065 Uiso 1 1 calc R . .
C7 C 0.07423(15) 0.24875(17) 0.5828(2) 0.0471(5) Uani 1 1 d . . .
H7 H 0.0551 0.2968 0.6289 0.057 Uiso 1 1 calc R . .
C8 C 0.09880(14) 0.26991(14) 0.47080(18) 0.0352(4) Uani 1 1 d . . .
O2 O 0.0000 0.5110(7) 0.2500 0.043(3) Uani 0.190(6) 2 d SPD . .
H2A H -0.053(8) 0.554(7) 0.202(12) 0.065 Uiso 0.190(6) 1 d PD . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S 0.1039(5) 0.0429(3) 0.0583(4) -0.0043(3) 0.0614(4) -0.0071(3)
O1 0.0593(9) 0.0418(8) 0.0517(8) -0.0091(7) 0.0356(7) -0.0020(7)
N1 0.0344(8) 0.0398(9) 0.0300(7) -0.0016(6) 0.0171(6) -0.0002(7)
N2 0.0494(10) 0.0375(9) 0.0358(8) -0.0028(7) 0.0272(8) 0.0001(7)
N3 0.0894(15) 0.0430(11) 0.0586(12) 0.0138(9) 0.0545(11) 0.0176(10)
C1 0.0442(11) 0.0399(11) 0.0383(10) -0.0042(8) 0.0228(9) -0.0043(9)
C2 0.0364(10) 0.0350(10) 0.0327(9) -0.0041(7) 0.0173(8) -0.0010(8)
C3 0.0281(9) 0.0404(10) 0.0322(9) -0.0013(8) 0.0140(7) -0.0043(8)
C4 0.0446(11) 0.0435(12) 0.0450(11) 0.0033(9) 0.0221(9) -0.0014(9)
C5 0.0542(13) 0.0584(15) 0.0568(13) 0.0157(11) 0.0301(11) -0.0037(11)
C6 0.0436(12) 0.0835(18) 0.0473(12) 0.0101(12) 0.0297(10) -0.0038(11)
C7 0.0378(11) 0.0681(15) 0.0425(11) -0.0059(10) 0.0239(9) -0.0023(10)
C8 0.0277(9) 0.0447(11) 0.0344(9) -0.0030(8) 0.0146(8) -0.0025(8)
O2 0.057(7) 0.040(7) 0.039(6) 0.000 0.027(5) 0.000
_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.
;
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
S C1 1.6896(19) . ?
O1 C8 1.357(2) . ?
O1 H1 0.88(3) . ?
N1 C2 1.282(2) . ?
N1 N2 1.382(2) . ?
N2 C1 1.344(2) . ?
N2 H2N 0.90(2) . ?
N3 C1 1.319(3) . ?
N3 H3A 0.86(3) . ?
N3 H3B 0.86(3) . ?
C2 C3 1.453(2) . ?
C2 H2 0.9400 . ?
C3 C4 1.396(3) . ?
C3 C8 1.401(3) . ?
C4 C5 1.381(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.383(3) . ?
C5 H5 0.9400 . ?
C6 C7 1.384(3) . ?
C6 H6 0.9400 . ?
C7 C8 1.390(3) . ?
C7 H7 0.9400 . ?
O2 H2A 0.92(5) . ?
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
C8 O1 H1 107.2(17) . . ?
C2 N1 N2 115.87(15) . . ?
C1 N2 N1 121.00(16) . . ?
C1 N2 H2N 120.6(14) . . ?
N1 N2 H2N 118.3(14) . . ?
C1 N3 H3A 121.6(19) . . ?
C1 N3 H3B 120.0(19) . . ?
H3A N3 H3B 118(3) . . ?
N3 C1 N2 118.49(17) . . ?
N3 C1 S 122.52(16) . . ?
N2 C1 S 118.98(15) . . ?
N1 C2 C3 122.18(16) . . ?
N1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C4 C3 C8 118.59(17) . . ?
C4 C3 C2 118.82(17) . . ?
C8 C3 C2 122.59(17) . . ?
C5 C4 C3 121.2(2) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 119.3(2) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C7 121.07(19) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C8 119.4(2) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
O1 C8 C7 117.67(18) . . ?
O1 C8 C3 121.88(16) . . ?
C7 C8 C3 120.44(19) . . ?
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
C2 N1 N2 C1 173.83(17) . . . . ?
N1 N2 C1 N3 1.0(3) . . . . ?
N1 N2 C1 S -178.62(13) . . . . ?
N2 N1 C2 C3 179.95(15) . . . . ?
N1 C2 C3 C4 179.81(17) . . . . ?
N1 C2 C3 C8 -0.4(3) . . . . ?
C8 C3 C4 C5 -0.2(3) . . . . ?
C2 C3 C4 C5 179.59(18) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C7 -0.5(3) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C6 C7 C8 O1 -178.81(18) . . . . ?
C6 C7 C8 C3 0.3(3) . . . . ?
C4 C3 C8 O1 178.89(17) . . . . ?
C2 C3 C8 O1 -0.9(3) . . . . ?
C4 C3 C8 C7 -0.2(3) . . . . ?
C2 C3 C8 C7 179.96(17) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.88(3) 1.87(3) 2.6567(19) 148(2) .
N2 H2N S 0.90(2) 2.53(2) 3.4199(18) 170.1(19) 7
N3 H3A O2 0.86(3) 2.30(3) 3.033(3) 144(2) .
N3 H3B O1 0.86(3) 2.09(3) 2.954(2) 177(3) 6_565
O2 H2A S 0.92(5) 2.05(6) 2.931(5) 159(11) 5_565
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 26.59
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max 0.320
_refine_diff_density_min -0.457
_refine_diff_density_rms 0.042
#===END
data_sk64_3fr
_database_code_depnum_ccdc_archive 'CCDC 771709'
#TrackingRef '- 1-xH2Ocrystaldata.CIF'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
Salicylaldehyde thiosemicarbazone 0.20hydrate;
(E)-2-(2-hydroxybenzylidene)hydrazinecarbothioamide 0.20hydrate
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C8 H9 N3 O S, 0.2(H2 O)'
_chemical_formula_sum 'C8 H9.40 N3 O1.20 S'
_chemical_formula_weight 198.89
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'
O O 0.0106 0.0060 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'C 2/c'
_symmetry_space_group_name_Hall '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a 13.8383(16)
_cell_length_b 14.3405(17)
_cell_length_c 10.5113(12)
_cell_angle_alpha 90.00
_cell_angle_beta 114.986(4)
_cell_angle_gamma 90.00
_cell_volume 1890.7(4)
_cell_formula_units_Z 8
_cell_measurement_temperature 203(2)
_cell_measurement_reflns_used 3863
_cell_measurement_theta_min 2.50
_cell_measurement_theta_max 29.18
_exptl_crystal_description plate
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.43
_exptl_crystal_size_mid 0.10
_exptl_crystal_size_min 0.08
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.397
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 832
_exptl_absorpt_coefficient_mu 0.308
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.8795
_exptl_absorpt_correction_T_max 0.9755
_exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 203(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker APEX II CCD area detector'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 13981
_diffrn_reflns_av_R_equivalents 0.0393
_diffrn_reflns_av_sigmaI/netI 0.0282
_diffrn_reflns_limit_h_min -17
_diffrn_reflns_limit_h_max 17
_diffrn_reflns_limit_k_min -18
_diffrn_reflns_limit_k_max 18
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_theta_min 2.16
_diffrn_reflns_theta_max 26.59
_reflns_number_total 1991
_reflns_number_gt 1617
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'APEX2 (Bruker, 2006)'
_computing_cell_refinement 'SAINT (Bruker, 2006)'
_computing_data_reduction SAINT
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'DIAMOND (Crystal Impact, 2009)'
_computing_publication_material ?
_publ_section_references
;
Bruker (2006). APEX2 (Version 2.1-0) and SAINT.
Bruker Analytical X-ray Systems, Madison, Wisconsin, USA.
Crystal Impact (2009). DIAMOND. Version 3.2d. Crystal Impact GbR, Bonn,
Germany.
Sheldrick, G. M. (1996). SADABS. University of G\"ottingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122.
;
_publ_section_exptl_refinement
;
Hydrogen atoms for aromatic CH were positioned geometrically
(C---H = 0.94 \%A) and refined
using a riding model, with U~iso~(H) = 1.2U~eq~(CH).
H atoms on the hydroxy and partly occupied crystal water oxygen atom,
on the amine and on the hydrazone nitrogen atom were found and
refined with U~iso~(H) = 1.5U~eq~(O,N). No DFIX restraints had
to be applied.
;
_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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0521P)^2^+2.0580P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 1991
_refine_ls_number_parameters 139
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0556
_refine_ls_R_factor_gt 0.0434
_refine_ls_wR_factor_ref 0.1198
_refine_ls_wR_factor_gt 0.1109
_refine_ls_goodness_of_fit_ref 1.039
_refine_ls_restrained_S_all 1.039
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
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
S S 0.20742(6) 0.39177(4) -0.07533(7) 0.0623(2) Uani 1 1 d . . .
O1 O 0.09743(12) 0.36112(10) 0.43870(16) 0.0480(4) Uani 1 1 d . . .
H1 H 0.114(2) 0.365(2) 0.364(3) 0.072 Uiso 1 1 d . . .
N1 N 0.14988(12) 0.29987(11) 0.23677(15) 0.0340(4) Uani 1 1 d . . .
N2 N 0.17719(14) 0.30662(11) 0.12535(17) 0.0384(4) Uani 1 1 d . . .
H2N H 0.2041(19) 0.2584(18) 0.103(2) 0.058 Uiso 1 1 d . . .
N3 N 0.13642(19) 0.46193(14) 0.1018(2) 0.0555(5) Uani 1 1 d . . .
H3A H 0.113(2) 0.459(2) 0.167(3) 0.083 Uiso 1 1 d . . .
H3B H 0.128(2) 0.514(2) 0.058(3) 0.083 Uiso 1 1 d . . .
C1 C 0.17101(16) 0.38788(14) 0.0594(2) 0.0401(4) Uani 1 1 d . . .
C2 C 0.15128(14) 0.21750(13) 0.28475(19) 0.0353(4) Uani 1 1 d . . .
H2 H 0.1696 0.1672 0.2420 0.042 Uiso 1 1 calc R . .
C3 C 0.12560(14) 0.19912(13) 0.40273(18) 0.0338(4) Uani 1 1 d . . .
C4 C 0.12850(17) 0.10733(15) 0.4485(2) 0.0455(5) Uani 1 1 d . . .
H4 H 0.1461 0.0590 0.4015 0.055 Uiso 1 1 calc R . .
C5 C 0.10608(19) 0.08606(18) 0.5613(3) 0.0561(6) Uani 1 1 d . . .
H5 H 0.1086 0.0239 0.5911 0.067 Uiso 1 1 calc R . .
C6 C 0.07997(18) 0.15699(19) 0.6299(2) 0.0561(6) Uani 1 1 d . . .
H6 H 0.0644 0.1427 0.7066 0.067 Uiso 1 1 calc R . .
C7 C 0.07641(16) 0.24856(17) 0.5877(2) 0.0486(5) Uani 1 1 d . . .
H7 H 0.0582 0.2962 0.6351 0.058 Uiso 1 1 calc R . .
C8 C 0.09979(14) 0.27010(14) 0.47497(19) 0.0370(4) Uani 1 1 d . . .
O2 O 0.0000 0.5115(4) 0.2500 0.0440(18) Uani 0.400(8) 2 d SP . .
H2A H -0.054(5) 0.556(5) 0.200(7) 0.066 Uiso 0.400(8) 1 d P . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S 0.1083(6) 0.0450(3) 0.0665(4) -0.0079(3) 0.0690(4) -0.0099(3)
O1 0.0619(10) 0.0423(8) 0.0509(9) -0.0082(7) 0.0346(8) 0.0007(7)
N1 0.0364(8) 0.0400(8) 0.0287(7) -0.0021(6) 0.0167(6) 0.0010(6)
N2 0.0502(10) 0.0380(9) 0.0352(8) -0.0038(7) 0.0261(7) 0.0007(7)
N3 0.0885(15) 0.0455(10) 0.0546(11) 0.0124(9) 0.0515(11) 0.0181(10)
C1 0.0469(11) 0.0415(11) 0.0378(10) -0.0055(8) 0.0237(9) -0.0048(8)
C2 0.0381(10) 0.0364(10) 0.0339(9) -0.0057(7) 0.0176(8) -0.0004(8)
C3 0.0290(9) 0.0408(10) 0.0304(9) -0.0027(7) 0.0113(7) -0.0020(7)
C4 0.0480(12) 0.0440(11) 0.0468(11) 0.0017(9) 0.0222(10) -0.0004(9)
C5 0.0554(13) 0.0592(14) 0.0596(14) 0.0164(11) 0.0299(11) -0.0022(11)
C6 0.0475(12) 0.0828(17) 0.0486(12) 0.0121(12) 0.0307(10) -0.0007(11)
C7 0.0413(11) 0.0696(15) 0.0423(11) -0.0058(10) 0.0248(9) 0.0010(10)
C8 0.0301(9) 0.0455(11) 0.0363(9) -0.0052(8) 0.0149(8) -0.0020(8)
O2 0.059(4) 0.041(3) 0.040(3) 0.000 0.029(3) 0.000
_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.
;
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
S C1 1.6931(19) . ?
O1 C8 1.356(3) . ?
O1 H1 0.91(3) . ?
N1 C2 1.281(2) . ?
N1 N2 1.378(2) . ?
N2 C1 1.340(3) . ?
N2 H2N 0.86(3) . ?
N3 C1 1.317(3) . ?
N3 H3A 0.87(3) . ?
N3 H3B 0.85(3) . ?
C2 C3 1.451(2) . ?
C2 H2 0.9400 . ?
C3 C4 1.396(3) . ?
C3 C8 1.403(3) . ?
C4 C5 1.381(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.380(4) . ?
C5 H5 0.9400 . ?
C6 C7 1.380(3) . ?
C6 H6 0.9400 . ?
C7 C8 1.389(3) . ?
C7 H7 0.9400 . ?
O2 H2A 0.96(7) . ?
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
C8 O1 H1 108.2(18) . . ?
C2 N1 N2 115.81(15) . . ?
C1 N2 N1 121.35(16) . . ?
C1 N2 H2N 119.9(17) . . ?
N1 N2 H2N 118.6(17) . . ?
C1 N3 H3A 122(2) . . ?
C1 N3 H3B 120(2) . . ?
H3A N3 H3B 117(3) . . ?
N3 C1 N2 118.65(18) . . ?
N3 C1 S 122.35(16) . . ?
N2 C1 S 118.99(15) . . ?
N1 C2 C3 122.37(16) . . ?
N1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
C4 C3 C8 118.33(18) . . ?
C4 C3 C2 118.92(17) . . ?
C8 C3 C2 122.73(17) . . ?
C5 C4 C3 121.3(2) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C6 C5 C4 119.3(2) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 121.0(2) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C8 119.8(2) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
O1 C8 C7 117.86(18) . . ?
O1 C8 C3 121.83(17) . . ?
C7 C8 C3 120.31(19) . . ?
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
C2 N1 N2 C1 174.96(18) . . . . ?
N1 N2 C1 N3 -1.1(3) . . . . ?
N1 N2 C1 S 179.15(14) . . . . ?
N2 N1 C2 C3 179.32(16) . . . . ?
N1 C2 C3 C4 179.73(18) . . . . ?
N1 C2 C3 C8 -1.5(3) . . . . ?
C8 C3 C4 C5 0.4(3) . . . . ?
C2 C3 C4 C5 179.18(19) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C6 C7 C8 O1 -178.71(19) . . . . ?
C6 C7 C8 C3 0.9(3) . . . . ?
C4 C3 C8 O1 178.65(18) . . . . ?
C2 C3 C8 O1 -0.1(3) . . . . ?
C4 C3 C8 C7 -0.9(3) . . . . ?
C2 C3 C8 C7 -179.65(17) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.91(3) 1.86(3) 2.665(2) 147(3) .
N2 H2N S 0.86(3) 2.56(3) 3.4102(18) 171(2) 7
N3 H3A O2 0.87(3) 2.23(3) 2.997(2) 148(3) .
N3 H3B O1 0.85(3) 2.13(3) 2.981(2) 176(3) 6_565
O2 H2A S 0.96(7) 2.10(7) 3.014(3) 159(6) 5_565
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 26.59
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max 0.479
_refine_diff_density_min -0.452
_refine_diff_density_rms 0.046
#===END