Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807019678/fl2127sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807019678/fl2127Isup2.hkl |
CCDC reference: 647691
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- H-atom completeness 65%
- Disorder in solvent or counterion
- R factor = 0.067
- wR factor = 0.198
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT221_ALERT_4_B Large Solvent/Anion S Ueq(max)/Ueq(min) ... 4.51 Ratio
Alert level C CHEMW03_ALERT_2_C The ratio of given/expected molecular weight as calculated from the _atom_site* data lies outside the range 0.99 <> 1.01 From the CIF: _cell_formula_units_Z 8 From the CIF: _chemical_formula_weight 427.50 TEST: Calculate formula weight from _atom_site_* atom mass num sum C 12.01 19.00 228.21 H 1.01 11.00 11.09 N 14.01 5.00 70.04 O 16.00 3.00 48.00 S 32.07 2.00 64.13 Calculated formula weight 421.46 PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT043_ALERT_1_C Check Reported Molecular Weight ................ 427.50 PLAT044_ALERT_1_C Calculated and Reported Dx Differ .............. ? PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.03 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C18 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C35 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for S3' PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for S4' PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for S3 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for O5 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for S4 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for O6 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C38 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 20.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 42.00 Deg. S3 -C35 -S3' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 44.50 Deg. S3' -C36 -S3 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 37.30 Deg. S4' -C37 -S4 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 36.70 Deg. S4 -C38 -S4' 1.555 1.555 1.555
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C19 H17 N5 O3 S2 Atom count from _chemical_formula_moiety:C19 H34 N5 O3 S2 FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C19 H17 N5 O3 S2 Atom count from the _atom_site data: C19 H11 N5 O3 S2 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional? From the CIF: _cell_formula_units_Z 8 From the CIF: _chemical_formula_sum C19 H17 N5 O3 S2 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 152.00 152.00 0.00 H 136.00 88.00 48.00 N 40.00 40.00 0.00 O 24.00 24.00 0.00 S 16.00 16.00 0.00 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 25 ALERT level C = Check and explain 6 ALERT level G = General alerts; check 11 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 9 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 11 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Che et al. (2006). For a similar crystal structure; Javad et al. (2005) and Singh et al. (1978). For synthesis, see: Rao, Kumar & Rao (1984); Rao, Rao & Girisham (1984).
All reagents were purchased (Adrich) and used without further purification. Compound (I) was synthesized according to the reference (Rao et al., 1984a). Then compound (I) (0.698 g, 0.002 mol) was dissolved into 20 ml DMSO. After heating at 70 °C for 20 min, the mixture was allowed to cool and evaporate naturally. Yellow block crystals of (I) suitable for single-crystal X-ray diffraction were obtained by evaporating the mixture at room temperature for a period of two weeks. Analysis found: C 53.5, H 4.0, N 16.4, S 14.8%; C19H17N5O3S2 requires: C 53.38, H 4.01, N 16.38, S 15.00%.
H atoms were generated geometrically and refined as riding atoms with C—H= 0.93 Å (CH), C—H= 0.96 Å (CH3), N—H= 0.86 Å (NH and NH2), Uiso(H)= 1.2 times Ueq(C) or Ueq(N) for CH, NH and NH2, Uiso(H)= 1.5 times Ueq(C) for CH3. The S3 snd s4 atom in the solvent DMSO molecules were disordered with refined occupancies of 0.805, 0.195 and 0.871, 0.129, respectively. Standard DFIX restraints were used for the dimensions of the disordered DMSO. The S atoms of the minor orientation were refined with an overall Uiso value. The H atoms attached to the disordered DMSO molecules were not located. All other non-H atoms were refined anisotropically. The maximum positive peak of 0.42 e Å-3 in the final difference electron density map is located 1.06 (1) Å from atom S4.
The thiosemicarbazide Schiff-base and its complexes are particularly widely studied because they are not only organic colorants with excellent performance and antibacterial & antiviral biological activities, but also templates for studying biocatalytic activity (Singh et al., 1978; Javad et al., 2005), but there are few studies of thiosemicarbazide Schiff-base synthesis (Rao et al., 1984a; Rao et al., 1984b). Recently, we have reported a crystal structure of the title compound (I) zinc complex (Che et al., 2006). Here we present crystal structure of (I).
There are two similar molecules of (I) and two DMSO solvent molecules in the asymmetric unit (Fig. 1). Bond distances and angles are very similar to the our previously reported zinc complex of (I) (Che et al., 2006). In the zinc complex of (I), each ligand (I) anion, which lost two H atoms on N2 and carboxyl O1, has two parts. One part, acting in tridentate chelating mode, coordinates to one ZnII through N2, N4 and S1, while another part coordinates to another ZnII through a monodentate carboxyl group. In the present Schiff-base (I), the H atoms on N2 and O1 are not lost. The N2 atom is also in the cis position with respect to N4 in the quinoxaline ring. All atoms (except the H atoms) in the molecule are nearly planar (the mean deviation of the atoms from the least-squares plane is 0.0590 Å). The crystal packing of (I) is stabilized by intermolecular N—H···O and N—H···N hydrogen-bond interactions (Table 1).
For related literature, see: Che et al. (2006). For a similar crystal structure; Javad et al. (2005) and Singh et al. (1978). For synthesis, see: Rao, Kumar & Rao (1984); Rao, Rao & Girisham (1984).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.
C17H28N5O2S·C2H6OS | F(000) = 1776 |
Mr = 427.50 | Dx = 1.381 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.876 (2) Å | Cell parameters from 2329 reflections |
b = 25.205 (3) Å | θ = 2.3–19.3° |
c = 11.0201 (15) Å | µ = 0.29 mm−1 |
β = 95.775 (3)° | T = 293 K |
V = 4111.0 (10) Å3 | Block, yellow |
Z = 8 | 0.43 × 0.15 × 0.15 mm |
Bruker SMART APEX2 CCD diffractometer | 7290 independent reflections |
Radiation source: fine-focus sealed tube | 4399 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
φ and ω scans | θmax = 25.1°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −17→16 |
Tmin = 0.888, Tmax = 0.958 | k = −23→30 |
21346 measured reflections | l = −12→13 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.067 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.198 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0964P)2 + 0.2132P] where P = (Fo2 + 2Fc2)/3 |
7290 reflections | (Δ/σ)max < 0.001 |
535 parameters | Δρmax = 0.42 e Å−3 |
18 restraints | Δρmin = −0.21 e Å−3 |
C17H28N5O2S·C2H6OS | V = 4111.0 (10) Å3 |
Mr = 427.50 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.876 (2) Å | µ = 0.29 mm−1 |
b = 25.205 (3) Å | T = 293 K |
c = 11.0201 (15) Å | 0.43 × 0.15 × 0.15 mm |
β = 95.775 (3)° |
Bruker SMART APEX2 CCD diffractometer | 7290 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 4399 reflections with I > 2σ(I) |
Tmin = 0.888, Tmax = 0.958 | Rint = 0.051 |
21346 measured reflections |
R[F2 > 2σ(F2)] = 0.067 | 18 restraints |
wR(F2) = 0.198 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.42 e Å−3 |
7290 reflections | Δρmin = −0.21 e Å−3 |
535 parameters |
Geometry. 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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S3 | 0.24586 (9) | 0.74512 (5) | 0.94383 (12) | 0.0586 (6) | 0.805 (5) |
S4 | 0.24527 (11) | 0.29402 (6) | 0.40349 (11) | 0.0670 (7) | 0.871 (5) |
S3' | 0.3110 (16) | 0.7249 (8) | 1.010 (2) | 0.264 (10)* | 0.195 (5) |
S4' | 0.1896 (15) | 0.2639 (9) | 0.4082 (17) | 0.162 (9)* | 0.129 (5) |
N1 | −0.0339 (2) | 0.61471 (15) | 0.6245 (3) | 0.0728 (10) | |
H1A | −0.0535 | 0.5838 | 0.6017 | 0.087* | |
H1B | −0.0523 | 0.6424 | 0.5836 | 0.087* | |
N2 | 0.0507 (2) | 0.57418 (13) | 0.7820 (3) | 0.0549 (8) | |
H2 | 0.0874 | 0.5761 | 0.8474 | 0.066* | |
N3 | 0.0204 (2) | 0.52559 (13) | 0.7415 (3) | 0.0530 (8) | |
N4 | 0.13007 (19) | 0.52554 (11) | 0.9956 (3) | 0.0450 (7) | |
N5 | 0.1421 (2) | 0.41785 (12) | 1.0816 (3) | 0.0582 (9) | |
N6 | 0.5545 (2) | 0.34561 (14) | 0.3731 (3) | 0.0725 (11) | |
H6A | 0.5718 | 0.3760 | 0.4021 | 0.087* | |
H6B | 0.5772 | 0.3171 | 0.4061 | 0.087* | |
N7 | 0.4613 (2) | 0.38960 (11) | 0.2319 (3) | 0.0518 (8) | |
H7N | 0.4222 | 0.3901 | 0.1688 | 0.062* | |
N8 | 0.49081 (19) | 0.43564 (12) | 0.2853 (3) | 0.0463 (8) | |
N9 | 0.37777 (18) | 0.45074 (11) | 0.0357 (2) | 0.0420 (7) | |
N10 | 0.37666 (19) | 0.56254 (11) | −0.0212 (3) | 0.0465 (8) | |
O1 | 0.2779 (2) | 0.63300 (12) | 1.3327 (3) | 0.0755 (9) | |
H1 | 0.2940 | 0.6551 | 1.3849 | 0.113* | |
O2 | 0.3298 (2) | 0.57660 (12) | 1.4791 (3) | 0.0819 (10) | |
O3 | 0.1741 (2) | 0.42962 (13) | −0.4565 (2) | 0.0813 (10) | |
O4 | 0.2167 (2) | 0.36383 (11) | −0.3284 (2) | 0.0666 (8) | |
H4 | 0.1962 | 0.3455 | −0.3862 | 0.100* | |
O5 | 0.3139 (2) | 0.78780 (12) | 0.9794 (3) | 0.0979 (12) | |
O6 | 0.1697 (2) | 0.29926 (12) | 0.4872 (3) | 0.0801 (9) | |
S1 | 0.06694 (10) | 0.67658 (5) | 0.77726 (13) | 0.0971 (5) | |
S2 | 0.45768 (10) | 0.28637 (5) | 0.21016 (13) | 0.0931 (5) | |
C1 | 0.0248 (3) | 0.61963 (16) | 0.7224 (4) | 0.0575 (11) | |
C2 | 0.0437 (2) | 0.48613 (16) | 0.8122 (4) | 0.0497 (10) | |
C3 | 0.0197 (3) | 0.43073 (17) | 0.7843 (4) | 0.0589 (11) | |
C4 | −0.0273 (3) | 0.40903 (19) | 0.6791 (4) | 0.0700 (13) | |
H4A | −0.0483 | 0.4306 | 0.6137 | 0.084* | |
C5 | −0.0416 (3) | 0.3553 (2) | 0.6751 (6) | 0.0921 (17) | |
H5 | −0.0719 | 0.3402 | 0.6056 | 0.111* | |
C6 | −0.0116 (4) | 0.3230 (2) | 0.7735 (6) | 0.0954 (18) | |
H6 | −0.0233 | 0.2867 | 0.7690 | 0.114* | |
C7 | 0.0357 (3) | 0.34383 (18) | 0.8793 (5) | 0.0808 (14) | |
H7 | 0.0554 | 0.3221 | 0.9450 | 0.097* | |
C8 | 0.0523 (3) | 0.39833 (16) | 0.8825 (4) | 0.0585 (11) | |
C9 | 0.0995 (2) | 0.43138 (15) | 0.9757 (4) | 0.0517 (10) | |
C10 | 0.0951 (2) | 0.48527 (15) | 0.9334 (3) | 0.0473 (9) | |
C11 | 0.1742 (2) | 0.51258 (14) | 1.1071 (3) | 0.0432 (9) | |
C12 | 0.1806 (3) | 0.45922 (15) | 1.1484 (3) | 0.0509 (10) | |
C13 | 0.2272 (3) | 0.44885 (17) | 1.2644 (4) | 0.0619 (11) | |
H13 | 0.2332 | 0.4141 | 1.2923 | 0.074* | |
C14 | 0.2633 (3) | 0.48922 (17) | 1.3356 (4) | 0.0577 (11) | |
H14 | 0.2935 | 0.4816 | 1.4116 | 0.069* | |
C15 | 0.2557 (2) | 0.54232 (16) | 1.2961 (3) | 0.0498 (9) | |
C16 | 0.2118 (2) | 0.55346 (15) | 1.1823 (3) | 0.0489 (9) | |
H16 | 0.2072 | 0.5884 | 1.1553 | 0.059* | |
C17 | 0.2914 (3) | 0.58507 (17) | 1.3783 (4) | 0.0581 (11) | |
C18 | 0.4934 (3) | 0.34274 (15) | 0.2781 (3) | 0.0549 (10) | |
C19 | 0.4676 (2) | 0.47900 (14) | 0.2286 (3) | 0.0414 (8) | |
C20 | 0.4953 (2) | 0.53187 (14) | 0.2728 (3) | 0.0437 (9) | |
C21 | 0.5442 (2) | 0.54663 (16) | 0.3814 (3) | 0.0529 (10) | |
H21 | 0.5641 | 0.5213 | 0.4393 | 0.063* | |
C22 | 0.5626 (3) | 0.59962 (17) | 0.4015 (4) | 0.0605 (11) | |
H22 | 0.5948 | 0.6102 | 0.4742 | 0.073* | |
C23 | 0.5337 (3) | 0.63772 (18) | 0.3143 (4) | 0.0695 (12) | |
H23 | 0.5472 | 0.6733 | 0.3295 | 0.083* | |
C24 | 0.4850 (3) | 0.62332 (16) | 0.2053 (4) | 0.0619 (11) | |
H24 | 0.4658 | 0.6488 | 0.1474 | 0.074* | |
C25 | 0.4657 (2) | 0.57004 (14) | 0.1849 (3) | 0.0454 (9) | |
C26 | 0.4162 (2) | 0.54262 (14) | 0.0815 (3) | 0.0424 (9) | |
C27 | 0.4160 (2) | 0.48737 (14) | 0.1083 (3) | 0.0407 (8) | |
C28 | 0.3352 (2) | 0.47041 (14) | −0.0723 (3) | 0.0408 (8) | |
C29 | 0.3351 (2) | 0.52530 (14) | −0.0997 (3) | 0.0430 (9) | |
C30 | 0.2910 (2) | 0.54193 (15) | −0.2124 (3) | 0.0514 (10) | |
H30 | 0.2896 | 0.5778 | −0.2324 | 0.062* | |
C31 | 0.2506 (2) | 0.50632 (17) | −0.2914 (3) | 0.0526 (10) | |
H31 | 0.2218 | 0.5182 | −0.3652 | 0.063* | |
C32 | 0.2509 (2) | 0.45140 (15) | −0.2652 (3) | 0.0478 (9) | |
C33 | 0.2926 (2) | 0.43428 (15) | −0.1562 (3) | 0.0438 (9) | |
H33 | 0.2928 | 0.3983 | −0.1374 | 0.053* | |
C34 | 0.2103 (3) | 0.41428 (18) | −0.3589 (3) | 0.0554 (11) | |
C35 | 0.2086 (7) | 0.7220 (3) | 1.0792 (7) | 0.180 (4) | |
C36 | 0.3075 (5) | 0.6881 (3) | 0.9071 (8) | 0.159 (3) | |
C37 | 0.2878 (4) | 0.2273 (2) | 0.4219 (5) | 0.114 (2) | |
C38 | 0.1898 (4) | 0.2855 (2) | 0.2531 (4) | 0.0961 (17) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S3 | 0.0611 (10) | 0.0390 (8) | 0.0715 (10) | −0.0050 (6) | −0.0128 (7) | 0.0021 (6) |
S4 | 0.0797 (12) | 0.0654 (10) | 0.0545 (8) | −0.0086 (7) | −0.0003 (7) | −0.0078 (6) |
N1 | 0.075 (3) | 0.078 (3) | 0.060 (2) | 0.000 (2) | −0.0169 (19) | 0.0062 (19) |
N2 | 0.050 (2) | 0.057 (2) | 0.0539 (19) | −0.0005 (16) | −0.0135 (15) | −0.0034 (16) |
N3 | 0.0436 (19) | 0.058 (2) | 0.057 (2) | −0.0015 (16) | 0.0012 (16) | −0.0157 (17) |
N4 | 0.0408 (18) | 0.0445 (18) | 0.0500 (18) | 0.0012 (14) | 0.0062 (14) | −0.0036 (15) |
N5 | 0.057 (2) | 0.046 (2) | 0.074 (2) | −0.0028 (16) | 0.0180 (19) | 0.0067 (18) |
N6 | 0.092 (3) | 0.052 (2) | 0.066 (2) | 0.0160 (19) | −0.024 (2) | 0.0004 (17) |
N7 | 0.060 (2) | 0.0424 (19) | 0.0503 (18) | −0.0031 (15) | −0.0105 (15) | −0.0024 (15) |
N8 | 0.0474 (19) | 0.0464 (19) | 0.0440 (17) | 0.0010 (15) | −0.0007 (14) | −0.0046 (15) |
N9 | 0.0411 (17) | 0.0447 (18) | 0.0398 (16) | 0.0014 (14) | 0.0030 (14) | −0.0022 (14) |
N10 | 0.0443 (18) | 0.0463 (18) | 0.0490 (18) | 0.0007 (14) | 0.0047 (15) | 0.0026 (15) |
O1 | 0.087 (2) | 0.065 (2) | 0.070 (2) | 0.0067 (17) | −0.0174 (17) | −0.0044 (16) |
O2 | 0.103 (3) | 0.081 (2) | 0.0570 (18) | −0.0100 (18) | −0.0135 (18) | 0.0059 (16) |
O3 | 0.095 (2) | 0.100 (2) | 0.0446 (17) | −0.0271 (18) | −0.0159 (16) | 0.0102 (16) |
O4 | 0.082 (2) | 0.065 (2) | 0.0500 (16) | −0.0034 (16) | −0.0073 (15) | −0.0073 (15) |
O5 | 0.120 (3) | 0.055 (2) | 0.108 (3) | −0.0283 (18) | −0.040 (2) | 0.0101 (18) |
O6 | 0.101 (3) | 0.080 (2) | 0.0588 (17) | 0.0047 (18) | 0.0047 (17) | −0.0224 (16) |
S1 | 0.1048 (11) | 0.0569 (8) | 0.1182 (11) | −0.0131 (7) | −0.0446 (9) | 0.0123 (7) |
S2 | 0.1140 (12) | 0.0498 (7) | 0.1095 (11) | −0.0076 (7) | −0.0181 (9) | −0.0135 (7) |
C1 | 0.048 (2) | 0.065 (3) | 0.057 (2) | 0.006 (2) | −0.0068 (19) | 0.006 (2) |
C2 | 0.035 (2) | 0.054 (3) | 0.061 (2) | −0.0012 (18) | 0.0104 (18) | −0.014 (2) |
C3 | 0.037 (2) | 0.063 (3) | 0.079 (3) | −0.0070 (19) | 0.016 (2) | −0.021 (2) |
C4 | 0.055 (3) | 0.073 (3) | 0.084 (3) | −0.012 (2) | 0.013 (2) | −0.030 (3) |
C5 | 0.075 (4) | 0.088 (4) | 0.114 (5) | −0.023 (3) | 0.018 (3) | −0.045 (4) |
C6 | 0.091 (4) | 0.067 (3) | 0.134 (5) | −0.030 (3) | 0.039 (4) | −0.043 (4) |
C7 | 0.080 (3) | 0.060 (3) | 0.108 (4) | −0.016 (3) | 0.032 (3) | −0.013 (3) |
C8 | 0.050 (3) | 0.053 (3) | 0.074 (3) | −0.008 (2) | 0.019 (2) | −0.011 (2) |
C9 | 0.039 (2) | 0.047 (2) | 0.072 (3) | −0.0016 (17) | 0.021 (2) | −0.003 (2) |
C10 | 0.035 (2) | 0.049 (2) | 0.059 (2) | −0.0006 (17) | 0.0090 (18) | −0.0066 (19) |
C11 | 0.038 (2) | 0.048 (2) | 0.046 (2) | 0.0015 (16) | 0.0119 (17) | 0.0011 (18) |
C12 | 0.049 (2) | 0.051 (2) | 0.055 (2) | 0.0004 (19) | 0.0156 (19) | 0.0034 (19) |
C13 | 0.065 (3) | 0.060 (3) | 0.063 (3) | 0.001 (2) | 0.016 (2) | 0.020 (2) |
C14 | 0.054 (3) | 0.069 (3) | 0.051 (2) | 0.000 (2) | 0.009 (2) | 0.014 (2) |
C15 | 0.041 (2) | 0.060 (3) | 0.049 (2) | −0.0007 (18) | 0.0080 (18) | 0.0031 (19) |
C16 | 0.042 (2) | 0.052 (2) | 0.053 (2) | 0.0022 (18) | 0.0105 (18) | 0.0032 (19) |
C17 | 0.053 (3) | 0.069 (3) | 0.052 (2) | 0.004 (2) | 0.005 (2) | 0.004 (2) |
C18 | 0.063 (3) | 0.046 (2) | 0.055 (2) | 0.002 (2) | 0.003 (2) | 0.0006 (19) |
C19 | 0.036 (2) | 0.049 (2) | 0.0389 (19) | −0.0010 (16) | 0.0036 (16) | −0.0031 (17) |
C20 | 0.039 (2) | 0.046 (2) | 0.046 (2) | 0.0025 (17) | 0.0063 (17) | −0.0060 (18) |
C21 | 0.051 (2) | 0.057 (3) | 0.050 (2) | −0.0055 (19) | 0.0042 (19) | −0.0063 (19) |
C22 | 0.056 (3) | 0.062 (3) | 0.063 (3) | −0.005 (2) | 0.003 (2) | −0.016 (2) |
C23 | 0.061 (3) | 0.054 (3) | 0.092 (3) | −0.007 (2) | 0.001 (2) | −0.019 (3) |
C24 | 0.058 (3) | 0.050 (3) | 0.076 (3) | 0.004 (2) | −0.003 (2) | 0.000 (2) |
C25 | 0.039 (2) | 0.045 (2) | 0.053 (2) | 0.0015 (16) | 0.0066 (17) | −0.0046 (18) |
C26 | 0.036 (2) | 0.043 (2) | 0.049 (2) | 0.0047 (16) | 0.0069 (17) | 0.0021 (17) |
C27 | 0.035 (2) | 0.045 (2) | 0.043 (2) | 0.0020 (16) | 0.0082 (16) | −0.0019 (17) |
C28 | 0.037 (2) | 0.053 (2) | 0.0333 (19) | 0.0033 (16) | 0.0069 (16) | 0.0030 (16) |
C29 | 0.041 (2) | 0.047 (2) | 0.042 (2) | 0.0038 (17) | 0.0078 (17) | 0.0026 (17) |
C30 | 0.054 (2) | 0.051 (2) | 0.049 (2) | 0.0052 (19) | 0.0083 (19) | 0.0083 (19) |
C31 | 0.047 (2) | 0.074 (3) | 0.037 (2) | 0.004 (2) | 0.0025 (18) | 0.008 (2) |
C32 | 0.040 (2) | 0.063 (3) | 0.041 (2) | −0.0038 (18) | 0.0080 (17) | 0.0012 (19) |
C33 | 0.042 (2) | 0.051 (2) | 0.039 (2) | −0.0021 (17) | 0.0023 (16) | 0.0004 (17) |
C34 | 0.048 (2) | 0.082 (3) | 0.037 (2) | −0.010 (2) | 0.0069 (18) | 0.001 (2) |
C35 | 0.239 (10) | 0.180 (8) | 0.134 (6) | −0.072 (7) | 0.082 (7) | 0.012 (6) |
C36 | 0.131 (6) | 0.094 (5) | 0.251 (9) | 0.032 (4) | 0.014 (6) | −0.070 (6) |
C37 | 0.127 (5) | 0.107 (5) | 0.109 (4) | 0.054 (4) | 0.013 (4) | 0.018 (4) |
C38 | 0.126 (5) | 0.110 (4) | 0.048 (3) | 0.014 (3) | −0.007 (3) | −0.007 (3) |
S3—O5 | 1.502 (3) | C3—C4 | 1.403 (6) |
S3—C35 | 1.743 (7) | C4—C5 | 1.371 (7) |
S3—C36 | 1.774 (6) | C4—H4A | 0.9300 |
S4—O6 | 1.530 (3) | C5—C6 | 1.393 (7) |
S4—C38 | 1.788 (5) | C5—H5 | 0.9300 |
S4—C37 | 1.800 (6) | C6—C7 | 1.402 (7) |
S3'—C36 | 1.46 (2) | C6—H6 | 0.9300 |
S3'—O5 | 1.62 (2) | C7—C8 | 1.395 (6) |
S3'—C35 | 1.77 (2) | C7—H7 | 0.9300 |
S4'—O6 | 1.301 (19) | C8—C9 | 1.448 (5) |
S4'—C37 | 1.721 (19) | C9—C10 | 1.435 (5) |
S4'—C38 | 1.794 (19) | C11—C16 | 1.403 (5) |
N1—C1 | 1.324 (5) | C11—C12 | 1.420 (5) |
N1—H1A | 0.8600 | C12—C13 | 1.416 (5) |
N1—H1B | 0.8600 | C13—C14 | 1.362 (6) |
N2—C1 | 1.357 (5) | C13—H13 | 0.9300 |
N2—N3 | 1.364 (4) | C14—C15 | 1.408 (5) |
N2—H2 | 0.8600 | C14—H14 | 0.9300 |
N3—C2 | 1.289 (5) | C15—C16 | 1.383 (5) |
N4—C10 | 1.304 (4) | C15—C17 | 1.472 (5) |
N4—C11 | 1.373 (4) | C16—H16 | 0.9300 |
N5—C9 | 1.316 (5) | C19—C20 | 1.464 (5) |
N5—C12 | 1.368 (5) | C19—C27 | 1.477 (5) |
N6—C18 | 1.318 (5) | C20—C21 | 1.388 (5) |
N6—H6A | 0.8600 | C20—C25 | 1.404 (5) |
N6—H6B | 0.8600 | C21—C22 | 1.377 (5) |
N7—C18 | 1.354 (4) | C21—H21 | 0.9300 |
N7—N8 | 1.354 (4) | C22—C23 | 1.396 (6) |
N7—H7N | 0.8600 | C22—H22 | 0.9300 |
N8—C19 | 1.289 (4) | C23—C24 | 1.387 (6) |
N9—C27 | 1.314 (4) | C23—H23 | 0.9300 |
N9—C28 | 1.383 (4) | C24—C25 | 1.387 (5) |
N10—C26 | 1.321 (4) | C24—H24 | 0.9300 |
N10—C29 | 1.379 (4) | C25—C26 | 1.466 (5) |
O1—C17 | 1.316 (5) | C26—C27 | 1.424 (5) |
O1—H1 | 0.8200 | C28—C33 | 1.402 (5) |
O2—C17 | 1.215 (5) | C28—C29 | 1.416 (5) |
O3—C34 | 1.216 (4) | C29—C30 | 1.409 (5) |
O4—C34 | 1.316 (5) | C30—C31 | 1.349 (5) |
O4—H4 | 0.8200 | C30—H30 | 0.9300 |
S1—C1 | 1.656 (4) | C31—C32 | 1.414 (5) |
S2—C18 | 1.668 (4) | C31—H31 | 0.9300 |
C2—C3 | 1.466 (5) | C32—C33 | 1.364 (5) |
C2—C10 | 1.471 (5) | C32—C34 | 1.478 (5) |
C3—C8 | 1.403 (6) | C33—H33 | 0.9300 |
O5—S3—C35 | 106.3 (3) | C14—C13—C12 | 120.8 (4) |
O5—S3—C36 | 106.8 (3) | C14—C13—H13 | 119.6 |
C35—S3—C36 | 98.0 (4) | C12—C13—H13 | 119.6 |
O6—S4—C38 | 105.7 (2) | C13—C14—C15 | 121.1 (4) |
O6—S4—C37 | 106.5 (2) | C13—C14—H14 | 119.4 |
C38—S4—C37 | 96.7 (3) | C15—C14—H14 | 119.4 |
C36—S3'—O5 | 117.3 (15) | C16—C15—C14 | 119.3 (4) |
C36—S3'—C35 | 110.0 (14) | C16—C15—C17 | 121.2 (4) |
O5—S3'—C35 | 100.0 (12) | C14—C15—C17 | 119.5 (4) |
O6—S4'—C37 | 123.7 (15) | C15—C16—C11 | 120.7 (4) |
O6—S4'—C38 | 116.8 (14) | C15—C16—H16 | 119.7 |
C37—S4'—C38 | 99.4 (10) | C11—C16—H16 | 119.7 |
C1—N1—H1A | 120.0 | O2—C17—O1 | 123.4 (4) |
C1—N1—H1B | 120.0 | O2—C17—C15 | 122.8 (4) |
H1A—N1—H1B | 120.0 | O1—C17—C15 | 113.9 (3) |
C1—N2—N3 | 122.1 (3) | N6—C18—N7 | 116.1 (3) |
C1—N2—H2 | 119.0 | N6—C18—S2 | 124.5 (3) |
N3—N2—H2 | 119.0 | N7—C18—S2 | 119.3 (3) |
C2—N3—N2 | 115.8 (3) | N8—C19—C20 | 123.9 (3) |
C10—N4—C11 | 114.5 (3) | N8—C19—C27 | 130.2 (3) |
C9—N5—C12 | 114.7 (3) | C20—C19—C27 | 105.8 (3) |
C18—N6—H6A | 120.0 | C21—C20—C25 | 120.8 (3) |
C18—N6—H6B | 120.0 | C21—C20—C19 | 129.6 (3) |
H6A—N6—H6B | 120.0 | C25—C20—C19 | 109.6 (3) |
C18—N7—N8 | 119.8 (3) | C22—C21—C20 | 118.5 (4) |
C18—N7—H7N | 120.1 | C22—C21—H21 | 120.7 |
N8—N7—H7N | 120.1 | C20—C21—H21 | 120.7 |
C19—N8—N7 | 117.1 (3) | C21—C22—C23 | 120.9 (4) |
C27—N9—C28 | 113.9 (3) | C21—C22—H22 | 119.5 |
C26—N10—C29 | 114.3 (3) | C23—C22—H22 | 119.5 |
C17—O1—H1 | 109.5 | C24—C23—C22 | 120.9 (4) |
C34—O4—H4 | 109.5 | C24—C23—H23 | 119.5 |
S3—O5—S3' | 47.4 (9) | C22—C23—H23 | 119.5 |
S4'—O6—S4 | 46.1 (11) | C23—C24—C25 | 118.4 (4) |
N1—C1—N2 | 116.6 (4) | C23—C24—H24 | 120.8 |
N1—C1—S1 | 125.0 (3) | C25—C24—H24 | 120.8 |
N2—C1—S1 | 118.5 (3) | C24—C25—C20 | 120.4 (3) |
N3—C2—C3 | 124.3 (4) | C24—C25—C26 | 131.5 (4) |
N3—C2—C10 | 130.0 (3) | C20—C25—C26 | 108.1 (3) |
C3—C2—C10 | 105.6 (4) | N10—C26—C27 | 122.7 (3) |
C8—C3—C4 | 121.0 (4) | N10—C26—C25 | 129.2 (3) |
C8—C3—C2 | 109.6 (4) | C27—C26—C25 | 108.1 (3) |
C4—C3—C2 | 129.4 (4) | N9—C27—C26 | 124.8 (3) |
C5—C4—C3 | 118.3 (5) | N9—C27—C19 | 126.9 (3) |
C5—C4—H4A | 120.8 | C26—C27—C19 | 108.3 (3) |
C3—C4—H4A | 120.8 | N9—C28—C33 | 118.1 (3) |
C4—C5—C6 | 121.1 (5) | N9—C28—C29 | 121.6 (3) |
C4—C5—H5 | 119.5 | C33—C28—C29 | 120.3 (3) |
C6—C5—H5 | 119.5 | N10—C29—C30 | 119.3 (3) |
C5—C6—C7 | 121.5 (5) | N10—C29—C28 | 122.7 (3) |
C5—C6—H6 | 119.2 | C30—C29—C28 | 117.9 (3) |
C7—C6—H6 | 119.2 | C31—C30—C29 | 120.6 (4) |
C8—C7—C6 | 117.5 (5) | C31—C30—H30 | 119.7 |
C8—C7—H7 | 121.2 | C29—C30—H30 | 119.7 |
C6—C7—H7 | 121.2 | C30—C31—C32 | 121.8 (3) |
C7—C8—C3 | 120.5 (4) | C30—C31—H31 | 119.1 |
C7—C8—C9 | 131.0 (4) | C32—C31—H31 | 119.1 |
C3—C8—C9 | 108.5 (4) | C33—C32—C31 | 118.8 (3) |
N5—C9—C10 | 122.4 (4) | C33—C32—C34 | 122.2 (4) |
N5—C9—C8 | 129.5 (4) | C31—C32—C34 | 118.9 (3) |
C10—C9—C8 | 108.1 (4) | C32—C33—C28 | 120.6 (3) |
N4—C10—C9 | 124.2 (4) | C32—C33—H33 | 119.7 |
N4—C10—C2 | 127.6 (3) | C28—C33—H33 | 119.7 |
C9—C10—C2 | 108.2 (3) | O3—C34—O4 | 123.2 (4) |
N4—C11—C16 | 118.7 (3) | O3—C34—C32 | 122.0 (4) |
N4—C11—C12 | 121.5 (3) | O4—C34—C32 | 114.8 (3) |
C16—C11—C12 | 119.8 (3) | S3—C35—S3' | 42.0 (8) |
N5—C12—C13 | 119.0 (4) | S3'—C36—S3 | 44.5 (10) |
N5—C12—C11 | 122.6 (3) | S4'—C37—S4 | 37.3 (8) |
C13—C12—C11 | 118.3 (4) | S4—C38—S4' | 36.7 (8) |
C1—N2—N3—C2 | −174.0 (3) | N7—N8—C19—C27 | −3.4 (5) |
C18—N7—N8—C19 | 170.9 (3) | N8—C19—C20—C21 | −4.5 (6) |
C35—S3—O5—S3' | 61.9 (11) | C27—C19—C20—C21 | 179.2 (3) |
C36—S3—O5—S3' | −42.0 (10) | N8—C19—C20—C25 | 174.6 (3) |
C36—S3'—O5—S3 | 61.0 (15) | C27—C19—C20—C25 | −1.7 (4) |
C35—S3'—O5—S3 | −57.7 (9) | C25—C20—C21—C22 | 0.4 (5) |
C37—S4'—O6—S4 | 62.5 (16) | C19—C20—C21—C22 | 179.4 (4) |
C38—S4'—O6—S4 | −61.5 (13) | C20—C21—C22—C23 | −0.6 (6) |
C38—S4—O6—S4' | 54.8 (12) | C21—C22—C23—C24 | 0.4 (6) |
C37—S4—O6—S4' | −47.3 (12) | C22—C23—C24—C25 | 0.0 (6) |
N3—N2—C1—N1 | 2.1 (6) | C23—C24—C25—C20 | −0.2 (6) |
N3—N2—C1—S1 | −178.7 (3) | C23—C24—C25—C26 | 179.5 (4) |
N2—N3—C2—C3 | −178.7 (3) | C21—C20—C25—C24 | 0.0 (5) |
N2—N3—C2—C10 | 2.9 (6) | C19—C20—C25—C24 | −179.2 (3) |
N3—C2—C3—C8 | −177.5 (4) | C21—C20—C25—C26 | −179.8 (3) |
C10—C2—C3—C8 | 1.3 (4) | C19—C20—C25—C26 | 1.0 (4) |
N3—C2—C3—C4 | 3.0 (6) | C29—N10—C26—C27 | 0.3 (5) |
C10—C2—C3—C4 | −178.3 (4) | C29—N10—C26—C25 | −179.7 (3) |
C8—C3—C4—C5 | 0.7 (6) | C24—C25—C26—N10 | 0.3 (7) |
C2—C3—C4—C5 | −179.8 (4) | C20—C25—C26—N10 | −179.9 (3) |
C3—C4—C5—C6 | 1.0 (7) | C24—C25—C26—C27 | −179.7 (4) |
C4—C5—C6—C7 | −1.2 (8) | C20—C25—C26—C27 | 0.1 (4) |
C5—C6—C7—C8 | −0.3 (7) | C28—N9—C27—C26 | −0.6 (5) |
C6—C7—C8—C3 | 2.0 (6) | C28—N9—C27—C19 | −179.0 (3) |
C6—C7—C8—C9 | −179.0 (4) | N10—C26—C27—N9 | 0.2 (5) |
C4—C3—C8—C7 | −2.2 (6) | C25—C26—C27—N9 | −179.9 (3) |
C2—C3—C8—C7 | 178.2 (3) | N10—C26—C27—C19 | 178.8 (3) |
C4—C3—C8—C9 | 178.6 (3) | C25—C26—C27—C19 | −1.2 (4) |
C2—C3—C8—C9 | −1.0 (4) | N8—C19—C27—N9 | 4.4 (6) |
C12—N5—C9—C10 | 0.8 (5) | C20—C19—C27—N9 | −179.6 (3) |
C12—N5—C9—C8 | 179.4 (4) | N8—C19—C27—C26 | −174.2 (3) |
C7—C8—C9—N5 | 2.5 (7) | C20—C19—C27—C26 | 1.8 (4) |
C3—C8—C9—N5 | −178.4 (4) | C27—N9—C28—C33 | 179.7 (3) |
C7—C8—C9—C10 | −178.7 (4) | C27—N9—C28—C29 | 0.7 (5) |
C3—C8—C9—C10 | 0.3 (4) | C26—N10—C29—C30 | −179.8 (3) |
C11—N4—C10—C9 | 1.0 (5) | C26—N10—C29—C28 | −0.2 (5) |
C11—N4—C10—C2 | 179.7 (3) | N9—C28—C29—N10 | −0.3 (5) |
N5—C9—C10—N4 | −1.8 (6) | C33—C28—C29—N10 | −179.3 (3) |
C8—C9—C10—N4 | 179.3 (3) | N9—C28—C29—C30 | 179.3 (3) |
N5—C9—C10—C2 | 179.3 (3) | C33—C28—C29—C30 | 0.3 (5) |
C8—C9—C10—C2 | 0.5 (4) | N10—C29—C30—C31 | 179.3 (3) |
N3—C2—C10—N4 | −1.2 (6) | C28—C29—C30—C31 | −0.4 (5) |
C3—C2—C10—N4 | −179.8 (3) | C29—C30—C31—C32 | −0.1 (6) |
N3—C2—C10—C9 | 177.6 (4) | C30—C31—C32—C33 | 0.6 (5) |
C3—C2—C10—C9 | −1.0 (4) | C30—C31—C32—C34 | −176.3 (3) |
C10—N4—C11—C16 | −178.1 (3) | C31—C32—C33—C28 | −0.7 (5) |
C10—N4—C11—C12 | 0.5 (5) | C34—C32—C33—C28 | 176.2 (3) |
C9—N5—C12—C13 | 179.3 (3) | N9—C28—C33—C32 | −178.8 (3) |
C9—N5—C12—C11 | 0.6 (5) | C29—C28—C33—C32 | 0.2 (5) |
N4—C11—C12—N5 | −1.4 (5) | C33—C32—C34—O3 | −179.2 (4) |
C16—C11—C12—N5 | 177.2 (3) | C31—C32—C34—O3 | −2.4 (6) |
N4—C11—C12—C13 | 180.0 (3) | C33—C32—C34—O4 | 0.7 (5) |
C16—C11—C12—C13 | −1.4 (5) | C31—C32—C34—O4 | 177.5 (3) |
N5—C12—C13—C14 | −177.4 (4) | O5—S3—C35—S3' | −62.6 (10) |
C11—C12—C13—C14 | 1.3 (6) | C36—S3—C35—S3' | 47.7 (10) |
C12—C13—C14—C15 | −0.2 (6) | C36—S3'—C35—S3 | −70.8 (14) |
C13—C14—C15—C16 | −0.9 (6) | O5—S3'—C35—S3 | 53.3 (9) |
C13—C14—C15—C17 | 176.7 (4) | O5—S3'—C36—S3 | −51.0 (12) |
C14—C15—C16—C11 | 0.7 (5) | C35—S3'—C36—S3 | 62.3 (12) |
C17—C15—C16—C11 | −176.8 (3) | O5—S3—C36—S3' | 51.1 (12) |
N4—C11—C16—C15 | 179.0 (3) | C35—S3—C36—S3' | −58.7 (12) |
C12—C11—C16—C15 | 0.4 (5) | O6—S4'—C37—S4 | −63.7 (18) |
C16—C15—C17—O2 | 179.6 (4) | C38—S4'—C37—S4 | 67.7 (10) |
C14—C15—C17—O2 | 2.1 (6) | O6—S4—C37—S4' | 41.4 (10) |
C16—C15—C17—O1 | −0.5 (5) | C38—S4—C37—S4' | −67.2 (11) |
C14—C15—C17—O1 | −178.1 (3) | O6—S4—C38—S4' | −45.6 (10) |
N8—N7—C18—N6 | −1.5 (5) | C37—S4—C38—S4' | 63.7 (10) |
N8—N7—C18—S2 | −179.0 (3) | O6—S4'—C38—S4 | 64.9 (16) |
N7—N8—C19—C20 | −178.8 (3) | C37—S4'—C38—S4 | −70.7 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
N7—H7N···N9 | 0.86 | 2.17 | 2.838 (4) | 134 |
N2—H2···N4 | 0.86 | 2.12 | 2.807 (4) | 137 |
N6—H6B···O5i | 0.86 | 2.09 | 2.820 (4) | 143 |
N6—H6A···O2ii | 0.86 | 2.21 | 2.982 (5) | 149 |
N1—H1B···O6iii | 0.86 | 2.36 | 3.131 (5) | 150 |
N1—H1A···O3iv | 0.86 | 2.30 | 2.872 (4) | 124 |
O4—H4···O6v | 0.82 | 1.83 | 2.642 (4) | 170 |
O1—H1···O5vi | 0.82 | 1.78 | 2.591 (4) | 168 |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, −y+1, −z+2; (iii) −x, −y+1, −z+1; (iv) −x, −y+1, −z; (v) x, y, z−1; (vi) x, −y+3/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C17H28N5O2S·C2H6OS |
Mr | 427.50 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 14.876 (2), 25.205 (3), 11.0201 (15) |
β (°) | 95.775 (3) |
V (Å3) | 4111.0 (10) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.29 |
Crystal size (mm) | 0.43 × 0.15 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART APEX2 CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2004) |
Tmin, Tmax | 0.888, 0.958 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21346, 7290, 4399 |
Rint | 0.051 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.067, 0.198, 1.04 |
No. of reflections | 7290 |
No. of parameters | 535 |
No. of restraints | 18 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.42, −0.21 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N7—H7N···N9 | 0.86 | 2.17 | 2.838 (4) | 133.7 |
N2—H2···N4 | 0.86 | 2.12 | 2.807 (4) | 136.8 |
N6—H6B···O5i | 0.86 | 2.09 | 2.820 (4) | 143.1 |
N6—H6A···O2ii | 0.86 | 2.21 | 2.982 (5) | 148.8 |
N1—H1B···O6iii | 0.86 | 2.36 | 3.131 (5) | 150.1 |
N1—H1A···O3iv | 0.86 | 2.30 | 2.872 (4) | 123.6 |
O4—H4···O6v | 0.82 | 1.83 | 2.642 (4) | 170.1 |
O1—H1···O5vi | 0.82 | 1.78 | 2.591 (4) | 168.1 |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, −y+1, −z+2; (iii) −x, −y+1, −z+1; (iv) −x, −y+1, −z; (v) x, y, z−1; (vi) x, −y+3/2, z+1/2. |
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The thiosemicarbazide Schiff-base and its complexes are particularly widely studied because they are not only organic colorants with excellent performance and antibacterial & antiviral biological activities, but also templates for studying biocatalytic activity (Singh et al., 1978; Javad et al., 2005), but there are few studies of thiosemicarbazide Schiff-base synthesis (Rao et al., 1984a; Rao et al., 1984b). Recently, we have reported a crystal structure of the title compound (I) zinc complex (Che et al., 2006). Here we present crystal structure of (I).
There are two similar molecules of (I) and two DMSO solvent molecules in the asymmetric unit (Fig. 1). Bond distances and angles are very similar to the our previously reported zinc complex of (I) (Che et al., 2006). In the zinc complex of (I), each ligand (I) anion, which lost two H atoms on N2 and carboxyl O1, has two parts. One part, acting in tridentate chelating mode, coordinates to one ZnII through N2, N4 and S1, while another part coordinates to another ZnII through a monodentate carboxyl group. In the present Schiff-base (I), the H atoms on N2 and O1 are not lost. The N2 atom is also in the cis position with respect to N4 in the quinoxaline ring. All atoms (except the H atoms) in the molecule are nearly planar (the mean deviation of the atoms from the least-squares plane is 0.0590 Å). The crystal packing of (I) is stabilized by intermolecular N—H···O and N—H···N hydrogen-bond interactions (Table 1).