Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051811/dn2239sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051811/dn2239Isup2.hkl |
CCDC reference: 656091
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.006 Å
- R factor = 0.073
- wR factor = 0.245
- Data-to-parameter ratio = 26.0
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 37 Perc. PLAT230_ALERT_2_B Hirshfeld Test Diff for C1A - C2A .. 8.79 su
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.90 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C4B PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C2A PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C2B PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C2B -C7B 1.36 Ang. PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 14
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.896 Tmax scaled 0.896 Tmin scaled 0.797
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Agarwal et al. (2006); Jing & Yu (2007); Jing et al. (2006); Nematollahi & Nulu (2006); Wu et al., (2000).
The potassium [N'-(2-methoxy-benzoyl)-hydrazinecarbodithioate] was synthesized by adding CS2 (4.3 ml, 45 mmol) to a methanol solution (25 ml) of 2-methoxybenzoic acid hydrazide (5.0 g, 30 mmol) in the presence of KOH (1.7 g, 30 mmol) and stirring the reaction mixture for 2 h at room temperature, yield (4.6 g, 92%), m.p. 260°C. IR (KBr, ν cm-1): 3367 m, 3235 m (–NH), 1620 s (>C=O), 994 m (C=S); 1H NMR (DMSO-d6, TMS): 12.01, 9.92 (s, 2H, –NH), 3.39 (s, 3H, –OCH3), 8.01, 7.53, 7.21, 7.12 (4H, aromatic); 13C NMR (DMSO-d6, TMS): 205.41 (C), 157.12 (C1), 119.07 (C2), 130.90 (C3), 120.87 (C4), 133.05 (C5), 112.22 (C6), 155.77 (C7), 56.32 (C8). Compound (I) was synthesized by dropwise addition of benzyl chloride (3 ml, 22 mmol) to a suspension of freshly prepared potassium [N'-(2-methoxy-benzoyl)-hydrazine]-carbodithioate (3 g, 11 mmol) in methanol (15 ml) and stirring the reaction mixture continuously for 2 h at room temperature. White single crystals of (I) (m.p. 383 K) suitable for X-ray analysis were obtained by slow evaporation of a methanol solution over a period of 1 d. (yield 1.74 g, 58%) IR (KBr, ν cm-1) 3251 m (–NH), 1658 s (>C=O), 1598 s (C=N), 877 m (C—S); 1H NMR (DMSO-d6, TMS): 11.42 (s, 1H, –NH), 3.17 (s, 3H, –OCH3), 4.29 (s, 4H, methylene); 8.03, 7.56, 7.34, 7.29 (m, 4H, aromatic); 7.19, 7.15, 7.09(m, 10H, phenyl), 13C NMR (DMSO-d6, TMS): 157.03 (C), 164.41 (C1), 119.56 (C2), 128.28 (C3), 121.17 (C4), 133.22 (C5), 112.33 (C6), 159.44 (C7), 56.56 (C8), 35.62 (C1A, C1B), 137.27 (C2A, C2B), 129.52 (C3A, C3B, C7A, C7B), 128.56 (C4A), 127.46 (C5A, C5B).
All H atoms were initially located in a difference Fourier map. The methyl H atoms were then constrained to an ideal geometry with C—H distances of 0.96Å and Uiso (H) = 1.5 Ueq (C), but each group was allowed to rotate freely about its C—C bond. The position of the hydrazinic H atom was refined freely along with an isotropic displacement parameter. All other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with an N—H distance of 0.86 Å and C—H distances in the range of 0.93–0.97 Å and Uiso(H) = 1.2 Ueq (C, N).
The acidhydrazides provide an interesting series of ligands whose properties can be altered by introducing different organic substituents (Jing et al.; 2006, 2007). Acidhydrazides compounds were tested for pharmacological properties such as MAO inhibitory activity (Nematollahi et al., 2006). Metal complexes based on acidhydrazides have attracted much attention because they show remarkable antifungal and antibacterial activites on different species of pathogenic fungi and bacteria (Agarwal et al., 2006). In spite of this, there is little information on substituted acids, in particulars those containing sulfur atoms. Therefore, as a part of our ongoing research, we report here the crystal structure of a new N2-bis(sulfanyl)derivative of 2-methoxybenzoic acid hydrazide.
The molecular structure of (I) can be divided into three different planes which contain one o-methoxyphenyl and two benzyl rings (Fig. 1). Atom O1 is in a trans configuration with respect to hydrazinic atom H1A. The dihedral angle between the o-methoxyphenyl ring and one benzyl ring (C6A, C5A, C4A, C3A, C2A and C7A) is 67.79 (9)°. Similarly the dihedral angle between the o-methoxyphenyl ring and the other benzyl ring (C3B, C4B, C5B, C6B, C7B and C2B) is 43.77(0.17)°. In addition, the C—S bond distances of 1.748 (3) Å agrees well with equivalent bonds in similar structures, being intermediate between 1.82 Å for a C—S single bond and 1.56 Å for a C=S double bond (Wu et al.; 2000). The corresponding C=N2 bond distance of 1.284 (4) Å is close to 1.299%A for a C=N double bond. The N1—N2 distance of 1.367 (3) Å shows partial double bond character, suggesting extensive delocalization in the (I). The three dimensional structure of I makes atoms O and N(2) potential neutral donor sites for coordination with metals. Intermolecular C—H···O hydrogen bonds link the molecules together in the solid state (Table 1, Fig 2). The crystal packing is also reinforced by a weak C—H···π interaction involving C3A–H3AA and the C2B to C7B carbons of the benzyl ring (centroid Cg) (Figure 2).
For related literature, see: Agarwal et al. (2006); Jing & Yu (2007); Jing et al. (2006); Nematollahi & Nulu (2006); Wu et al., (2000).
Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).
C23H22N2O2S2 | F(000) = 888 |
Mr = 422.55 | Dx = 1.302 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4189 reflections |
a = 13.0233 (6) Å | θ = 4.9–32.5° |
b = 8.4361 (4) Å | µ = 0.27 mm−1 |
c = 20.3957 (11) Å | T = 296 K |
β = 105.849 (5)° | Prism, colorless |
V = 2155.61 (18) Å3 | 0.55 × 0.49 × 0.41 mm |
Z = 4 |
Oxford Diffraction Gemini R diffractometer | 6835 independent reflections |
Radiation source: fine-focus sealed tube | 2543 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 32.6°, θmin = 4.9° |
φ and ω scans | h = −18→19 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | k = −11→12 |
Tmin = 0.890, Tmax = 1.000 | l = −30→29 |
16045 measured reflections |
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)] = 0.073 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.245 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0797P)2 + 0.9801P] where P = (Fo2 + 2Fc2)/3 |
6835 reflections | (Δ/σ)max < 0.001 |
263 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
C23H22N2O2S2 | V = 2155.61 (18) Å3 |
Mr = 422.55 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.0233 (6) Å | µ = 0.27 mm−1 |
b = 8.4361 (4) Å | T = 296 K |
c = 20.3957 (11) Å | 0.55 × 0.49 × 0.41 mm |
β = 105.849 (5)° |
Oxford Diffraction Gemini R diffractometer | 6835 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | 2543 reflections with I > 2σ(I) |
Tmin = 0.890, Tmax = 1.000 | Rint = 0.045 |
16045 measured reflections |
R[F2 > 2σ(F2)] = 0.073 | 0 restraints |
wR(F2) = 0.245 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.30 e Å−3 |
6835 reflections | Δρmin = −0.34 e Å−3 |
263 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 | ||
S1 | 0.13312 (9) | 0.80835 (13) | 0.30775 (5) | 0.0928 (4) | |
S2 | 0.28700 (8) | 0.64554 (11) | 0.41899 (5) | 0.0806 (3) | |
O1 | 0.2976 (2) | 1.2281 (3) | 0.49188 (16) | 0.1075 (10) | |
O2 | 0.46878 (18) | 0.8278 (3) | 0.57408 (13) | 0.0796 (7) | |
N1 | 0.32261 (19) | 0.9691 (3) | 0.47724 (12) | 0.0603 (6) | |
H1A | 0.3562 | 0.8839 | 0.4936 | 0.072* | |
N2 | 0.2479 (2) | 0.9653 (3) | 0.41540 (13) | 0.0643 (6) | |
C1C | 0.2270 (2) | 0.8288 (4) | 0.38701 (17) | 0.0663 (8) | |
C1 | 0.3440 (2) | 1.1050 (4) | 0.51253 (16) | 0.0626 (7) | |
C2 | 0.4278 (2) | 1.0997 (4) | 0.57988 (15) | 0.0594 (7) | |
C3 | 0.4481 (3) | 1.2410 (4) | 0.61549 (19) | 0.0781 (9) | |
H3A | 0.4109 | 1.3315 | 0.5965 | 0.094* | |
C4 | 0.5222 (3) | 1.2513 (5) | 0.6786 (2) | 0.0943 (12) | |
H4A | 0.5341 | 1.3474 | 0.7018 | 0.113* | |
C5 | 0.5780 (3) | 1.1185 (6) | 0.7067 (2) | 0.0975 (12) | |
H5A | 0.6280 | 1.1251 | 0.7490 | 0.117* | |
C6 | 0.5609 (3) | 0.9769 (5) | 0.67312 (19) | 0.0812 (10) | |
H6A | 0.5993 | 0.8878 | 0.6927 | 0.097* | |
C7 | 0.4866 (2) | 0.9647 (4) | 0.60990 (16) | 0.0622 (8) | |
C8 | 0.5294 (3) | 0.6904 (5) | 0.6005 (2) | 0.0999 (13) | |
H8A | 0.5092 | 0.6050 | 0.5685 | 0.150* | |
H8B | 0.5159 | 0.6608 | 0.6428 | 0.150* | |
H8C | 0.6040 | 0.7127 | 0.6080 | 0.150* | |
C1A | 0.0768 (3) | 1.0064 (5) | 0.2923 (2) | 0.0932 (12) | |
H1AA | 0.0045 | 0.9976 | 0.2630 | 0.112* | |
H1AB | 0.0723 | 1.0502 | 0.3354 | 0.112* | |
C2A | 0.1364 (2) | 1.1207 (5) | 0.26046 (18) | 0.0723 (9) | |
C3A | 0.1507 (3) | 1.0933 (6) | 0.1966 (2) | 0.0888 (11) | |
H3AA | 0.1235 | 1.0014 | 0.1730 | 0.107* | |
C4A | 0.2047 (4) | 1.2008 (6) | 0.1677 (2) | 0.1008 (13) | |
H4AA | 0.2141 | 1.1802 | 0.1249 | 0.121* | |
C5A | 0.2447 (4) | 1.3368 (6) | 0.2007 (3) | 0.0991 (13) | |
H5AA | 0.2815 | 1.4082 | 0.1807 | 0.119* | |
C6A | 0.2308 (3) | 1.3677 (5) | 0.2630 (3) | 0.0935 (12) | |
H6AA | 0.2569 | 1.4614 | 0.2854 | 0.112* | |
C7A | 0.1778 (3) | 1.2601 (5) | 0.2932 (2) | 0.0857 (11) | |
H7AA | 0.1697 | 1.2816 | 0.3363 | 0.103* | |
C1B | 0.1757 (3) | 0.5587 (4) | 0.4454 (2) | 0.0821 (10) | |
H1BA | 0.1143 | 0.5501 | 0.4060 | 0.099* | |
H1BB | 0.1952 | 0.4524 | 0.4625 | 0.099* | |
C2B | 0.1451 (3) | 0.6530 (4) | 0.49929 (19) | 0.0681 (8) | |
C3B | 0.0472 (4) | 0.7176 (5) | 0.4877 (3) | 0.1067 (14) | |
H3BA | −0.0035 | 0.7042 | 0.4460 | 0.128* | |
C4B | 0.0228 (5) | 0.8088 (7) | 0.5419 (4) | 0.141 (2) | |
H4BA | −0.0445 | 0.8530 | 0.5362 | 0.169* | |
C5B | 0.0992 (5) | 0.8280 (7) | 0.6004 (3) | 0.1288 (19) | |
H5BA | 0.0842 | 0.8892 | 0.6346 | 0.155* | |
C6B | 0.1938 (4) | 0.7648 (7) | 0.6116 (2) | 0.1102 (15) | |
H6BA | 0.2446 | 0.7802 | 0.6531 | 0.132* | |
C7B | 0.2170 (3) | 0.6766 (5) | 0.5623 (2) | 0.0893 (11) | |
H7BA | 0.2840 | 0.6299 | 0.5711 | 0.107* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0911 (7) | 0.0908 (7) | 0.0824 (7) | −0.0100 (5) | −0.0002 (5) | −0.0070 (5) |
S2 | 0.0829 (6) | 0.0688 (6) | 0.0918 (7) | 0.0140 (5) | 0.0268 (5) | −0.0093 (5) |
O1 | 0.123 (2) | 0.0589 (15) | 0.115 (2) | 0.0307 (15) | −0.0097 (17) | −0.0049 (14) |
O2 | 0.0721 (14) | 0.0592 (14) | 0.0934 (17) | 0.0192 (11) | −0.0015 (12) | −0.0010 (12) |
N1 | 0.0641 (15) | 0.0477 (13) | 0.0659 (15) | 0.0120 (11) | 0.0120 (12) | 0.0026 (12) |
N2 | 0.0626 (14) | 0.0667 (17) | 0.0598 (15) | 0.0057 (13) | 0.0104 (12) | 0.0051 (13) |
C1C | 0.0596 (17) | 0.069 (2) | 0.070 (2) | 0.0050 (16) | 0.0180 (15) | 0.0000 (16) |
C1 | 0.0639 (17) | 0.0512 (17) | 0.0705 (19) | 0.0132 (15) | 0.0143 (15) | 0.0048 (15) |
C2 | 0.0594 (16) | 0.0566 (17) | 0.0662 (18) | 0.0019 (14) | 0.0238 (14) | −0.0067 (15) |
C3 | 0.079 (2) | 0.064 (2) | 0.090 (3) | −0.0039 (18) | 0.021 (2) | −0.0124 (19) |
C4 | 0.092 (3) | 0.090 (3) | 0.101 (3) | −0.014 (2) | 0.026 (2) | −0.033 (3) |
C5 | 0.083 (3) | 0.120 (4) | 0.084 (3) | −0.006 (3) | 0.012 (2) | −0.015 (3) |
C6 | 0.072 (2) | 0.087 (3) | 0.080 (2) | 0.0040 (19) | 0.0126 (18) | 0.002 (2) |
C7 | 0.0518 (16) | 0.0645 (19) | 0.0710 (19) | 0.0038 (15) | 0.0178 (15) | −0.0002 (16) |
C8 | 0.098 (3) | 0.068 (2) | 0.122 (3) | 0.030 (2) | 0.011 (2) | 0.014 (2) |
C1A | 0.0583 (19) | 0.125 (3) | 0.085 (2) | 0.015 (2) | 0.0006 (18) | −0.009 (2) |
C2A | 0.0506 (16) | 0.084 (2) | 0.074 (2) | 0.0220 (17) | 0.0020 (15) | −0.0002 (19) |
C3A | 0.081 (2) | 0.100 (3) | 0.079 (2) | 0.013 (2) | 0.0104 (19) | −0.018 (2) |
C4A | 0.101 (3) | 0.125 (4) | 0.076 (3) | 0.005 (3) | 0.025 (2) | −0.006 (3) |
C5A | 0.100 (3) | 0.093 (3) | 0.101 (3) | 0.016 (2) | 0.022 (3) | 0.013 (3) |
C6A | 0.083 (3) | 0.074 (3) | 0.113 (3) | 0.018 (2) | 0.009 (2) | −0.001 (2) |
C7A | 0.075 (2) | 0.095 (3) | 0.078 (2) | 0.031 (2) | 0.0060 (19) | −0.013 (2) |
C1B | 0.094 (2) | 0.0500 (18) | 0.100 (3) | −0.0014 (18) | 0.023 (2) | −0.0062 (18) |
C2B | 0.0705 (19) | 0.0512 (17) | 0.082 (2) | 0.0035 (16) | 0.0208 (17) | 0.0084 (16) |
C3B | 0.086 (3) | 0.098 (3) | 0.126 (4) | 0.018 (2) | 0.013 (3) | −0.004 (3) |
C4B | 0.094 (4) | 0.147 (5) | 0.184 (6) | 0.038 (3) | 0.044 (4) | −0.021 (4) |
C5B | 0.116 (4) | 0.145 (5) | 0.135 (5) | 0.005 (4) | 0.050 (4) | −0.028 (4) |
C6B | 0.106 (4) | 0.147 (4) | 0.082 (3) | −0.009 (3) | 0.034 (3) | 0.004 (3) |
C7B | 0.087 (3) | 0.098 (3) | 0.086 (3) | 0.004 (2) | 0.026 (2) | 0.015 (2) |
S1—C1C | 1.749 (4) | C1A—H1AB | 0.9700 |
S1—C1A | 1.817 (4) | C2A—C3A | 1.385 (5) |
S2—C1C | 1.775 (3) | C2A—C7A | 1.387 (5) |
S2—C1B | 1.832 (4) | C3A—C4A | 1.375 (6) |
O1—C1 | 1.217 (4) | C3A—H3AA | 0.9300 |
O2—C7 | 1.352 (4) | C4A—C5A | 1.360 (6) |
O2—C8 | 1.423 (4) | C4A—H4AA | 0.9300 |
N1—C1 | 1.342 (4) | C5A—C6A | 1.356 (6) |
N1—N2 | 1.367 (3) | C5A—H5AA | 0.9300 |
N1—H1A | 0.8600 | C6A—C7A | 1.383 (6) |
N2—C1C | 1.284 (4) | C6A—H6AA | 0.9300 |
C1—C2 | 1.504 (4) | C7A—H7AA | 0.9300 |
C2—C3 | 1.383 (5) | C1B—C2B | 1.496 (5) |
C2—C7 | 1.415 (4) | C1B—H1BA | 0.9700 |
C3—C4 | 1.385 (6) | C1B—H1BB | 0.9700 |
C3—H3A | 0.9300 | C2B—C3B | 1.348 (5) |
C4—C5 | 1.373 (6) | C2B—C7B | 1.383 (5) |
C4—H4A | 0.9300 | C3B—C4B | 1.452 (7) |
C5—C6 | 1.365 (6) | C3B—H3BA | 0.9300 |
C5—H5A | 0.9300 | C4B—C5B | 1.339 (8) |
C6—C7 | 1.389 (5) | C4B—H4BA | 0.9300 |
C6—H6A | 0.9300 | C5B—C6B | 1.304 (7) |
C8—H8A | 0.9600 | C5B—H5BA | 0.9300 |
C8—H8B | 0.9600 | C6B—C7B | 1.349 (6) |
C8—H8C | 0.9600 | C6B—H6BA | 0.9300 |
C1A—C2A | 1.493 (5) | C7B—H7BA | 0.9300 |
C1A—H1AA | 0.9700 | ||
C1C—S1—C1A | 102.53 (17) | C3A—C2A—C7A | 117.4 (4) |
C1C—S2—C1B | 98.75 (16) | C3A—C2A—C1A | 121.4 (4) |
C7—O2—C8 | 119.7 (3) | C7A—C2A—C1A | 121.2 (3) |
C1—N1—N2 | 120.4 (2) | C4A—C3A—C2A | 120.6 (4) |
C1—N1—H1A | 119.8 | C4A—C3A—H3AA | 119.7 |
N2—N1—H1A | 119.8 | C2A—C3A—H3AA | 119.7 |
C1C—N2—N1 | 116.6 (3) | C5A—C4A—C3A | 121.0 (4) |
N2—C1C—S1 | 120.9 (3) | C5A—C4A—H4AA | 119.5 |
N2—C1C—S2 | 126.7 (3) | C3A—C4A—H4AA | 119.5 |
S1—C1C—S2 | 112.4 (2) | C6A—C5A—C4A | 119.7 (5) |
O1—C1—N1 | 122.2 (3) | C6A—C5A—H5AA | 120.2 |
O1—C1—C2 | 120.6 (3) | C4A—C5A—H5AA | 120.2 |
N1—C1—C2 | 117.2 (3) | C5A—C6A—C7A | 120.1 (4) |
C3—C2—C7 | 117.6 (3) | C5A—C6A—H6AA | 119.9 |
C3—C2—C1 | 116.1 (3) | C7A—C6A—H6AA | 119.9 |
C7—C2—C1 | 126.2 (3) | C6A—C7A—C2A | 121.1 (4) |
C2—C3—C4 | 121.8 (4) | C6A—C7A—H7AA | 119.4 |
C2—C3—H3A | 119.1 | C2A—C7A—H7AA | 119.4 |
C4—C3—H3A | 119.1 | C2B—C1B—S2 | 113.2 (2) |
C5—C4—C3 | 119.5 (4) | C2B—C1B—H1BA | 108.9 |
C5—C4—H4A | 120.3 | S2—C1B—H1BA | 108.9 |
C3—C4—H4A | 120.3 | C2B—C1B—H1BB | 108.9 |
C6—C5—C4 | 120.6 (4) | S2—C1B—H1BB | 108.9 |
C6—C5—H5A | 119.7 | H1BA—C1B—H1BB | 107.7 |
C4—C5—H5A | 119.7 | C3B—C2B—C7B | 118.2 (4) |
C5—C6—C7 | 120.5 (4) | C3B—C2B—C1B | 121.0 (4) |
C5—C6—H6A | 119.8 | C7B—C2B—C1B | 120.7 (3) |
C7—C6—H6A | 119.8 | C2B—C3B—C4B | 118.3 (5) |
O2—C7—C6 | 122.5 (3) | C2B—C3B—H3BA | 120.8 |
O2—C7—C2 | 117.4 (3) | C4B—C3B—H3BA | 120.8 |
C6—C7—C2 | 120.0 (3) | C5B—C4B—C3B | 118.6 (5) |
O2—C8—H8A | 109.5 | C5B—C4B—H4BA | 120.7 |
O2—C8—H8B | 109.5 | C3B—C4B—H4BA | 120.7 |
H8A—C8—H8B | 109.5 | C6B—C5B—C4B | 122.9 (5) |
O2—C8—H8C | 109.5 | C6B—C5B—H5BA | 118.5 |
H8A—C8—H8C | 109.5 | C4B—C5B—H5BA | 118.5 |
H8B—C8—H8C | 109.5 | C5B—C6B—C7B | 119.2 (5) |
C2A—C1A—S1 | 115.8 (2) | C5B—C6B—H6BA | 120.4 |
C2A—C1A—H1AA | 108.3 | C7B—C6B—H6BA | 120.4 |
S1—C1A—H1AA | 108.3 | C6B—C7B—C2B | 122.7 (4) |
C2A—C1A—H1AB | 108.3 | C6B—C7B—H7BA | 118.7 |
S1—C1A—H1AB | 108.3 | C2B—C7B—H7BA | 118.7 |
H1AA—C1A—H1AB | 107.4 | ||
C1—N1—N2—C1C | −175.5 (3) | C3—C2—C7—C6 | 0.4 (4) |
N1—N2—C1C—S1 | −179.8 (2) | C1—C2—C7—C6 | −179.1 (3) |
N1—N2—C1C—S2 | −1.3 (4) | C1C—S1—C1A—C2A | 85.3 (3) |
C1A—S1—C1C—N2 | −6.7 (3) | S1—C1A—C2A—C3A | 61.4 (4) |
C1A—S1—C1C—S2 | 174.60 (19) | S1—C1A—C2A—C7A | −120.0 (3) |
C1B—S2—C1C—N2 | 106.3 (3) | C7A—C2A—C3A—C4A | 0.5 (5) |
C1B—S2—C1C—S1 | −75.1 (2) | C1A—C2A—C3A—C4A | 179.2 (3) |
N2—N1—C1—O1 | 1.0 (5) | C2A—C3A—C4A—C5A | −0.5 (6) |
N2—N1—C1—C2 | −179.5 (2) | C3A—C4A—C5A—C6A | −0.3 (7) |
O1—C1—C2—C3 | −0.2 (5) | C4A—C5A—C6A—C7A | 1.1 (6) |
N1—C1—C2—C3 | −179.7 (3) | C5A—C6A—C7A—C2A | −1.1 (6) |
O1—C1—C2—C7 | 179.3 (3) | C3A—C2A—C7A—C6A | 0.3 (5) |
N1—C1—C2—C7 | −0.1 (4) | C1A—C2A—C7A—C6A | −178.4 (3) |
C7—C2—C3—C4 | −0.6 (5) | C1C—S2—C1B—C2B | −61.5 (3) |
C1—C2—C3—C4 | 179.0 (3) | S2—C1B—C2B—C3B | 118.1 (4) |
C2—C3—C4—C5 | 0.5 (6) | S2—C1B—C2B—C7B | −61.7 (4) |
C3—C4—C5—C6 | −0.2 (6) | C7B—C2B—C3B—C4B | 0.2 (6) |
C4—C5—C6—C7 | 0.0 (6) | C1B—C2B—C3B—C4B | −179.6 (4) |
C8—O2—C7—C6 | −1.5 (5) | C2B—C3B—C4B—C5B | 1.6 (8) |
C8—O2—C7—C2 | 177.1 (3) | C3B—C4B—C5B—C6B | −2.0 (10) |
C5—C6—C7—O2 | 178.4 (3) | C4B—C5B—C6B—C7B | 0.5 (9) |
C5—C6—C7—C2 | −0.1 (5) | C5B—C6B—C7B—C2B | 1.5 (7) |
C3—C2—C7—O2 | −178.2 (3) | C3B—C2B—C7B—C6B | −1.8 (6) |
C1—C2—C7—O2 | 2.3 (4) | C1B—C2B—C7B—C6B | 178.0 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2 | 0.86 | 1.94 | 2.625 (3) | 136 |
C1B—H1BB···O1i | 0.97 | 2.30 | 3.220 (4) | 159 |
N1—H1A···S2 | 0.86 | 2.53 | 2.963 (3) | 112 |
Symmetry code: (i) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C23H22N2O2S2 |
Mr | 422.55 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 13.0233 (6), 8.4361 (4), 20.3957 (11) |
β (°) | 105.849 (5) |
V (Å3) | 2155.61 (18) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.27 |
Crystal size (mm) | 0.55 × 0.49 × 0.41 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini R |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2007) |
Tmin, Tmax | 0.890, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16045, 6835, 2543 |
Rint | 0.045 |
(sin θ/λ)max (Å−1) | 0.758 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.073, 0.245, 1.08 |
No. of reflections | 6835 |
No. of parameters | 263 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.34 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2 | 0.86 | 1.94 | 2.625 (3) | 136.1 |
C1B—H1BB···O1i | 0.97 | 2.30 | 3.220 (4) | 158.6 |
N1—H1A···S2 | 0.86 | 2.53 | 2.963 (3) | 111.7 |
Symmetry code: (i) x, y−1, z. |
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The acidhydrazides provide an interesting series of ligands whose properties can be altered by introducing different organic substituents (Jing et al.; 2006, 2007). Acidhydrazides compounds were tested for pharmacological properties such as MAO inhibitory activity (Nematollahi et al., 2006). Metal complexes based on acidhydrazides have attracted much attention because they show remarkable antifungal and antibacterial activites on different species of pathogenic fungi and bacteria (Agarwal et al., 2006). In spite of this, there is little information on substituted acids, in particulars those containing sulfur atoms. Therefore, as a part of our ongoing research, we report here the crystal structure of a new N2-bis(sulfanyl)derivative of 2-methoxybenzoic acid hydrazide.
The molecular structure of (I) can be divided into three different planes which contain one o-methoxyphenyl and two benzyl rings (Fig. 1). Atom O1 is in a trans configuration with respect to hydrazinic atom H1A. The dihedral angle between the o-methoxyphenyl ring and one benzyl ring (C6A, C5A, C4A, C3A, C2A and C7A) is 67.79 (9)°. Similarly the dihedral angle between the o-methoxyphenyl ring and the other benzyl ring (C3B, C4B, C5B, C6B, C7B and C2B) is 43.77(0.17)°. In addition, the C—S bond distances of 1.748 (3) Å agrees well with equivalent bonds in similar structures, being intermediate between 1.82 Å for a C—S single bond and 1.56 Å for a C=S double bond (Wu et al.; 2000). The corresponding C=N2 bond distance of 1.284 (4) Å is close to 1.299%A for a C=N double bond. The N1—N2 distance of 1.367 (3) Å shows partial double bond character, suggesting extensive delocalization in the (I). The three dimensional structure of I makes atoms O and N(2) potential neutral donor sites for coordination with metals. Intermolecular C—H···O hydrogen bonds link the molecules together in the solid state (Table 1, Fig 2). The crystal packing is also reinforced by a weak C—H···π interaction involving C3A–H3AA and the C2B to C7B carbons of the benzyl ring (centroid Cg) (Figure 2).