Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055080/zl2079sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055080/zl2079Isup2.hkl |
CCDC reference: 672855
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.035
- wR factor = 0.092
- Data-to-parameter ratio = 23.3
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.752 0.908 Tmin(prime) and Tmax expected: 0.853 0.908 RR(prime) = 0.882 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.88 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 14
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For a related structure, see: Boschi et al. (2003). For related background (biological, anticancer and antimicrobial activity), see: Bharti et al. (2000); Chan et al. (2003).
Potassium 2-furoic acid hydrazide carbodithioate was prepared by adding carbon disulfide (0.04 mol, 2.4 ml) to a solution of furan-2-carboxylic acid hydrazide (0.02 mol, 2.52 g) and potassium hydroxide (0.02 mol, 1.12 g) in methanol (30 ml) and stirring the reaction mixture for 2 h. The solid that separated was filtered off, washed with a 10% (v/v) mixture of ethanol-ether and dried in vacuo. yield 1.44 g, 60%, m.p. 438 K. The title ompound was prepared by drop wise addition of benzyl chloride (0.02 mol, 2.53 g) to a suspension of a potassium salt of 2-furoic acid hydrazide carbodithioate (0.01 mol, 2.28 g) in methanol (20 ml) and stirring the reaction mixture for a period of 5–6 h. The reaction mixture was filtered and the solution was evaporated almost to dryness. The solid was washed several times with carbon tetrachloride and then with chloroform and recrystalized from methanol. Transparent white shining crystals of the title compound (m.p. 388 K), suitable for X-ray analysis were obtained by slow evaporation of the methanol solution over a period of three weeks (yield 1.91 g, 50%): Analysis found: C 62.82, H 4.75, N 7.40, S 16.85; C20H18N2O2S2 requires: C 62.74, H 4.70, N 7.32, S 16.73.
The amide hydrogen atom (H2A) was located in a difference Fourier map and along with all other H atoms were placed in their calculated positions and then refined using the riding model with N—H = 0.86 Å; C—H = 0.93 to 0.97 Å, and Uiso(H) = 1.18–1.22Ueq(C,N). The maximum residual electron density peaks of 0.486 and -0.297 e Å3, were located at 0.68 Å from CA2 and 0.27 Å from H6A.
Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 2006); program(s) used to solve structure: SHELXS90 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).
C20H18N2O2S2 | Z = 2 |
Mr = 382.48 | F(000) = 400 |
Triclinic, P1 | Dx = 1.397 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.2058 (14) Å | Cell parameters from 8953 reflections |
b = 9.2663 (14) Å | θ = 2.2–30.6° |
c = 11.3877 (17) Å | µ = 0.31 mm−1 |
α = 109.983 (2)° | T = 100 K |
β = 94.781 (2)° | Prism, colorless |
γ = 90.201 (3)° | 0.50 × 0.48 × 0.31 mm |
V = 909.2 (2) Å3 |
Bruker SMART CCD area detector diffractometer | 5473 independent reflections |
Radiation source: fine-focus sealed tube | 5150 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
ϕ and ω scans | θmax = 30.5°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1999) | h = −12→13 |
Tmin = 0.752, Tmax = 0.908 | k = −13→13 |
10879 measured reflections | l = −16→16 |
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0478P)2 + 0.3812P] where P = (Fo2 + 2Fc2)/3 |
5473 reflections | (Δ/σ)max = 0.002 |
235 parameters | Δρmax = 0.48 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C20H18N2O2S2 | γ = 90.201 (3)° |
Mr = 382.48 | V = 909.2 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.2058 (14) Å | Mo Kα radiation |
b = 9.2663 (14) Å | µ = 0.31 mm−1 |
c = 11.3877 (17) Å | T = 100 K |
α = 109.983 (2)° | 0.50 × 0.48 × 0.31 mm |
β = 94.781 (2)° |
Bruker SMART CCD area detector diffractometer | 5473 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1999) | 5150 reflections with I > 2σ(I) |
Tmin = 0.752, Tmax = 0.908 | Rint = 0.016 |
10879 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.48 e Å−3 |
5473 reflections | Δρmin = −0.29 e Å−3 |
235 parameters |
Experimental. Spectroscopic analysis: IR(KBr,ν cm-1): 3310, (–NH); 1680, (C=O); 1583, (Thiomide I[β(NH + ν(CN)]; 1277, (Thioamide II [ν(CN) + β(NH)]; 754, (Thioamide IV, /n (C—S); 1074 /n (N—N). 1H NMR (CDCl3,δ, p.p.m.): 9.70, (s, 1H, NH); 4.25, (d, 2H, –CH2); 7.76–7.89, (m, 3H, furan ring); 7.31–7.46, (m, 5H, phenyl); 13C NMR (CDCl3, δ, p.p.m.): 178.61, (C—S); 160.30, (C=O); 145.40, (C3); 115.92, (C4); 112.52, (C5); 144.36, (C6); 153.12, (C2A); 112.34, (C3A,7 A); 129.76, (C4A,6 A); 127.78, (C5A); 36.86, (CH2). |
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 | ||
S1A | 0.83197 (3) | 0.46195 (3) | 0.31516 (2) | 0.01799 (7) | |
S1B | 0.83350 (3) | 0.69808 (3) | 0.57280 (2) | 0.01936 (7) | |
O1 | 1.31416 (9) | 0.81929 (11) | 0.44309 (8) | 0.02540 (18) | |
O2 | 1.15179 (9) | 1.05449 (10) | 0.71366 (8) | 0.02291 (17) | |
N1 | 1.03648 (10) | 0.68224 (11) | 0.41270 (8) | 0.01901 (18) | |
N2 | 1.08610 (10) | 0.81545 (11) | 0.50926 (9) | 0.01960 (18) | |
H2A | 1.0290 | 0.8610 | 0.5657 | 0.024* | |
C1 | 0.91710 (12) | 0.62306 (12) | 0.43136 (9) | 0.01711 (18) | |
C2 | 1.22268 (12) | 0.87532 (12) | 0.51658 (10) | 0.01811 (19) | |
C3 | 1.25246 (12) | 1.01706 (12) | 0.62573 (10) | 0.01824 (19) | |
C4 | 1.36458 (13) | 1.12278 (13) | 0.66080 (11) | 0.0227 (2) | |
H4A | 1.4459 | 1.1235 | 0.6177 | 0.027* | |
C5 | 1.33189 (15) | 1.23308 (14) | 0.77784 (12) | 0.0270 (2) | |
H5A | 1.3882 | 1.3201 | 0.8257 | 0.032* | |
C6 | 1.20373 (15) | 1.18689 (14) | 0.80570 (12) | 0.0273 (2) | |
H6A | 1.1575 | 1.2380 | 0.8773 | 0.033* | |
C1A | 0.95464 (12) | 0.43706 (14) | 0.19310 (10) | 0.0206 (2) | |
H1AA | 0.9687 | 0.5337 | 0.1794 | 0.025* | |
H1AB | 1.0488 | 0.4057 | 0.2190 | 0.025* | |
C2A | 0.89122 (11) | 0.31695 (12) | 0.07338 (10) | 0.01711 (19) | |
C3A | 0.84726 (12) | 0.35829 (13) | −0.03044 (10) | 0.0194 (2) | |
H3AA | 0.8530 | 0.4610 | −0.0239 | 0.023* | |
C4A | 0.79483 (13) | 0.24774 (14) | −0.14391 (10) | 0.0231 (2) | |
H4AA | 0.7684 | 0.2762 | −0.2133 | 0.028* | |
C5A | 0.78214 (13) | 0.09491 (14) | −0.15297 (11) | 0.0247 (2) | |
H5AA | 0.7470 | 0.0207 | −0.2285 | 0.030* | |
C6A | 0.82198 (13) | 0.05301 (13) | −0.04922 (12) | 0.0250 (2) | |
H6AA | 0.8114 | −0.0490 | −0.0547 | 0.030* | |
C7A | 0.87777 (13) | 0.16316 (13) | 0.06314 (11) | 0.0217 (2) | |
H7AA | 0.9063 | 0.1340 | 0.1318 | 0.026* | |
C1B | 0.66064 (12) | 0.59096 (14) | 0.54544 (10) | 0.0215 (2) | |
H1BA | 0.5962 | 0.6137 | 0.4827 | 0.026* | |
H1BB | 0.6758 | 0.4813 | 0.5174 | 0.026* | |
C2B | 0.59769 (11) | 0.64384 (12) | 0.67084 (10) | 0.01821 (19) | |
C3B | 0.62147 (12) | 0.56157 (13) | 0.75201 (11) | 0.0217 (2) | |
H3BA | 0.6725 | 0.4712 | 0.7275 | 0.026* | |
C4B | 0.56896 (13) | 0.61435 (14) | 0.87003 (11) | 0.0234 (2) | |
H4BA | 0.5854 | 0.5592 | 0.9242 | 0.028* | |
C5B | 0.49201 (13) | 0.74924 (14) | 0.90733 (11) | 0.0234 (2) | |
H5BA | 0.4572 | 0.7843 | 0.9862 | 0.028* | |
C6B | 0.46754 (13) | 0.83113 (14) | 0.82611 (11) | 0.0235 (2) | |
H6BA | 0.4158 | 0.9211 | 0.8505 | 0.028* | |
C7B | 0.52029 (12) | 0.77887 (13) | 0.70825 (11) | 0.0207 (2) | |
H7BA | 0.5039 | 0.8342 | 0.6542 | 0.025* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.01715 (12) | 0.02079 (13) | 0.01268 (11) | −0.00613 (9) | 0.00220 (9) | 0.00130 (9) |
S1B | 0.01660 (12) | 0.02282 (13) | 0.01414 (12) | −0.00608 (9) | 0.00312 (9) | 0.00017 (9) |
O1 | 0.0206 (4) | 0.0314 (4) | 0.0182 (4) | −0.0067 (3) | 0.0048 (3) | 0.0001 (3) |
O2 | 0.0243 (4) | 0.0205 (4) | 0.0195 (4) | −0.0025 (3) | 0.0052 (3) | 0.0004 (3) |
N1 | 0.0188 (4) | 0.0197 (4) | 0.0148 (4) | −0.0059 (3) | 0.0013 (3) | 0.0012 (3) |
N2 | 0.0186 (4) | 0.0192 (4) | 0.0164 (4) | −0.0057 (3) | 0.0042 (3) | −0.0003 (3) |
C1 | 0.0178 (4) | 0.0188 (4) | 0.0126 (4) | −0.0030 (3) | 0.0014 (3) | 0.0027 (3) |
C2 | 0.0182 (5) | 0.0200 (5) | 0.0150 (4) | −0.0044 (4) | 0.0002 (4) | 0.0048 (4) |
C3 | 0.0184 (5) | 0.0190 (5) | 0.0163 (4) | −0.0025 (4) | 0.0012 (4) | 0.0048 (4) |
C4 | 0.0226 (5) | 0.0229 (5) | 0.0209 (5) | −0.0069 (4) | −0.0016 (4) | 0.0065 (4) |
C5 | 0.0328 (6) | 0.0196 (5) | 0.0238 (5) | −0.0061 (4) | −0.0034 (5) | 0.0028 (4) |
C6 | 0.0348 (6) | 0.0197 (5) | 0.0212 (5) | −0.0008 (4) | 0.0028 (5) | −0.0012 (4) |
C1A | 0.0184 (5) | 0.0274 (5) | 0.0131 (4) | −0.0067 (4) | 0.0024 (4) | 0.0032 (4) |
C2A | 0.0151 (4) | 0.0206 (5) | 0.0136 (4) | −0.0017 (3) | 0.0033 (3) | 0.0029 (4) |
C3A | 0.0215 (5) | 0.0199 (5) | 0.0158 (4) | −0.0022 (4) | 0.0027 (4) | 0.0049 (4) |
C4A | 0.0245 (5) | 0.0277 (6) | 0.0150 (5) | −0.0029 (4) | 0.0006 (4) | 0.0049 (4) |
C5A | 0.0228 (5) | 0.0236 (5) | 0.0198 (5) | −0.0034 (4) | 0.0033 (4) | −0.0029 (4) |
C6A | 0.0244 (5) | 0.0169 (5) | 0.0303 (6) | 0.0004 (4) | 0.0055 (4) | 0.0032 (4) |
C7A | 0.0212 (5) | 0.0227 (5) | 0.0222 (5) | 0.0011 (4) | 0.0026 (4) | 0.0087 (4) |
C1B | 0.0172 (5) | 0.0261 (5) | 0.0162 (4) | −0.0073 (4) | 0.0032 (4) | 0.0003 (4) |
C2B | 0.0138 (4) | 0.0210 (5) | 0.0162 (4) | −0.0047 (3) | 0.0022 (3) | 0.0015 (4) |
C3B | 0.0190 (5) | 0.0219 (5) | 0.0228 (5) | 0.0003 (4) | 0.0043 (4) | 0.0053 (4) |
C4B | 0.0216 (5) | 0.0287 (6) | 0.0204 (5) | −0.0018 (4) | 0.0034 (4) | 0.0089 (4) |
C5B | 0.0196 (5) | 0.0282 (6) | 0.0184 (5) | −0.0037 (4) | 0.0055 (4) | 0.0020 (4) |
C6B | 0.0190 (5) | 0.0222 (5) | 0.0256 (5) | 0.0004 (4) | 0.0066 (4) | 0.0024 (4) |
C7B | 0.0175 (5) | 0.0223 (5) | 0.0218 (5) | −0.0018 (4) | 0.0027 (4) | 0.0065 (4) |
S1A—C1 | 1.7500 (11) | C3A—C4A | 1.3928 (15) |
S1A—C1A | 1.8179 (11) | C3A—H3AA | 0.9300 |
S1B—C1 | 1.7648 (11) | C4A—C5A | 1.3881 (17) |
S1B—C1B | 1.8192 (11) | C4A—H4AA | 0.9300 |
O1—C2 | 1.2259 (14) | C5A—C6A | 1.3868 (18) |
O2—C6 | 1.3659 (14) | C5A—H5AA | 0.9300 |
O2—C3 | 1.3789 (13) | C6A—C7A | 1.3917 (17) |
N1—C1 | 1.2915 (14) | C6A—H6AA | 0.9300 |
N1—N2 | 1.3879 (12) | C7A—H7AA | 0.9300 |
N2—C2 | 1.3571 (14) | C1B—C2B | 1.5090 (15) |
N2—H2A | 0.8600 | C1B—H1BA | 0.9700 |
C2—C3 | 1.4731 (15) | C1B—H1BB | 0.9700 |
C3—C4 | 1.3570 (15) | C2B—C3B | 1.3902 (16) |
C4—C5 | 1.4316 (17) | C2B—C7B | 1.3954 (16) |
C4—H4A | 0.9300 | C3B—C4B | 1.3927 (16) |
C5—C6 | 1.3518 (19) | C3B—H3BA | 0.9300 |
C5—H5A | 0.9300 | C4B—C5B | 1.3922 (17) |
C6—H6A | 0.9300 | C4B—H4BA | 0.9300 |
C1A—C2A | 1.5046 (15) | C5B—C6B | 1.3886 (18) |
C1A—H1AA | 0.9700 | C5B—H5BA | 0.9300 |
C1A—H1AB | 0.9700 | C6B—C7B | 1.3920 (16) |
C2A—C3A | 1.3925 (15) | C6B—H6BA | 0.9300 |
C2A—C7A | 1.3937 (16) | C7B—H7BA | 0.9300 |
C1—S1A—C1A | 99.49 (5) | C5A—C4A—C3A | 119.75 (11) |
C1—S1B—C1B | 105.31 (5) | C5A—C4A—H4AA | 120.1 |
C6—O2—C3 | 106.42 (9) | C3A—C4A—H4AA | 120.1 |
C1—N1—N2 | 114.05 (9) | C6A—C5A—C4A | 119.89 (10) |
C2—N2—N1 | 121.44 (9) | C6A—C5A—H5AA | 120.1 |
C2—N2—H2A | 119.3 | C4A—C5A—H5AA | 120.1 |
N1—N2—H2A | 119.3 | C5A—C6A—C7A | 120.21 (11) |
N1—C1—S1A | 120.42 (8) | C5A—C6A—H6AA | 119.9 |
N1—C1—S1B | 122.38 (8) | C7A—C6A—H6AA | 119.9 |
S1A—C1—S1B | 117.20 (6) | C6A—C7A—C2A | 120.43 (11) |
O1—C2—N2 | 125.12 (10) | C6A—C7A—H7AA | 119.8 |
O1—C2—C3 | 122.36 (10) | C2A—C7A—H7AA | 119.8 |
N2—C2—C3 | 112.51 (9) | C2B—C1B—S1B | 104.83 (7) |
C4—C3—O2 | 110.42 (10) | C2B—C1B—H1BA | 110.8 |
C4—C3—C2 | 132.44 (10) | S1B—C1B—H1BA | 110.8 |
O2—C3—C2 | 117.14 (9) | C2B—C1B—H1BB | 110.8 |
C3—C4—C5 | 105.83 (11) | S1B—C1B—H1BB | 110.8 |
C3—C4—H4A | 127.1 | H1BA—C1B—H1BB | 108.9 |
C5—C4—H4A | 127.1 | C3B—C2B—C7B | 119.53 (10) |
C6—C5—C4 | 107.05 (10) | C3B—C2B—C1B | 120.15 (10) |
C6—C5—H5A | 126.5 | C7B—C2B—C1B | 120.27 (10) |
C4—C5—H5A | 126.5 | C2B—C3B—C4B | 120.07 (11) |
C5—C6—O2 | 110.29 (11) | C2B—C3B—H3BA | 120.0 |
C5—C6—H6A | 124.9 | C4B—C3B—H3BA | 120.0 |
O2—C6—H6A | 124.9 | C5B—C4B—C3B | 120.34 (11) |
C2A—C1A—S1A | 109.68 (7) | C5B—C4B—H4BA | 119.8 |
C2A—C1A—H1AA | 109.7 | C3B—C4B—H4BA | 119.8 |
S1A—C1A—H1AA | 109.7 | C6B—C5B—C4B | 119.65 (11) |
C2A—C1A—H1AB | 109.7 | C6B—C5B—H5BA | 120.2 |
S1A—C1A—H1AB | 109.7 | C4B—C5B—H5BA | 120.2 |
H1AA—C1A—H1AB | 108.2 | C5B—C6B—C7B | 120.12 (11) |
C3A—C2A—C7A | 118.85 (10) | C5B—C6B—H6BA | 119.9 |
C3A—C2A—C1A | 119.96 (10) | C7B—C6B—H6BA | 119.9 |
C7A—C2A—C1A | 121.18 (10) | C6B—C7B—C2B | 120.28 (11) |
C2A—C3A—C4A | 120.83 (10) | C6B—C7B—H7BA | 119.9 |
C2A—C3A—H3AA | 119.6 | C2B—C7B—H7BA | 119.9 |
C4A—C3A—H3AA | 119.6 | ||
C1—N1—N2—C2 | 166.99 (10) | S1A—C1A—C2A—C3A | 113.50 (10) |
N2—N1—C1—S1A | 175.81 (8) | S1A—C1A—C2A—C7A | −67.69 (12) |
N2—N1—C1—S1B | −4.57 (14) | C7A—C2A—C3A—C4A | −1.93 (16) |
C1A—S1A—C1—N1 | −2.02 (11) | C1A—C2A—C3A—C4A | 176.90 (10) |
C1A—S1A—C1—S1B | 178.35 (7) | C2A—C3A—C4A—C5A | 1.86 (17) |
C1B—S1B—C1—N1 | 173.39 (10) | C3A—C4A—C5A—C6A | −0.14 (18) |
C1B—S1B—C1—S1A | −6.99 (8) | C4A—C5A—C6A—C7A | −1.47 (18) |
N1—N2—C2—O1 | −1.29 (18) | C5A—C6A—C7A—C2A | 1.39 (18) |
N1—N2—C2—C3 | 179.69 (10) | C3A—C2A—C7A—C6A | 0.31 (16) |
C6—O2—C3—C4 | −0.17 (13) | C1A—C2A—C7A—C6A | −178.51 (10) |
C6—O2—C3—C2 | 178.91 (10) | C1—S1B—C1B—C2B | 174.10 (8) |
O1—C2—C3—C4 | 10.0 (2) | S1B—C1B—C2B—C3B | −94.13 (11) |
N2—C2—C3—C4 | −170.94 (12) | S1B—C1B—C2B—C7B | 83.28 (11) |
O1—C2—C3—O2 | −168.84 (11) | C7B—C2B—C3B—C4B | −0.35 (16) |
N2—C2—C3—O2 | 10.22 (14) | C1B—C2B—C3B—C4B | 177.07 (10) |
O2—C3—C4—C5 | −0.02 (13) | C2B—C3B—C4B—C5B | 0.23 (17) |
C2—C3—C4—C5 | −178.92 (12) | C3B—C4B—C5B—C6B | 0.09 (17) |
C3—C4—C5—C6 | 0.21 (14) | C4B—C5B—C6B—C7B | −0.28 (17) |
C4—C5—C6—O2 | −0.33 (15) | C5B—C6B—C7B—C2B | 0.15 (17) |
C3—O2—C6—C5 | 0.32 (14) | C3B—C2B—C7B—C6B | 0.17 (16) |
C1—S1A—C1A—C2A | −171.49 (8) | C1B—C2B—C7B—C6B | −177.26 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O2 | 0.86 | 2.22 | 2.6310 (12) | 109 |
N2—H2A···S1B | 0.86 | 2.37 | 2.8132 (10) | 113 |
C4—H4A···O1i | 0.93 | 2.48 | 3.3823 (15) | 164 |
C4A—H4AA···O1ii | 0.93 | 2.51 | 3.3136 (15) | 145 |
C5B—H5BA···Cg1iii | 0.95 | 2.81 | 3.4504 (14) | 127 |
Symmetry codes: (i) −x+3, −y+2, −z+1; (ii) −x+2, −y+1, −z; (iii) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C20H18N2O2S2 |
Mr | 382.48 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 9.2058 (14), 9.2663 (14), 11.3877 (17) |
α, β, γ (°) | 109.983 (2), 94.781 (2), 90.201 (3) |
V (Å3) | 909.2 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.31 |
Crystal size (mm) | 0.50 × 0.48 × 0.31 |
Data collection | |
Diffractometer | Bruker SMART CCD area detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1999) |
Tmin, Tmax | 0.752, 0.908 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10879, 5473, 5150 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.715 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.092, 1.05 |
No. of reflections | 5473 |
No. of parameters | 235 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.48, −0.29 |
Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 2006), SHELXS90 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O2 | 0.86 | 2.22 | 2.6310 (12) | 109.1 |
N2—H2A···S1B | 0.86 | 2.37 | 2.8132 (10) | 112.5 |
C4—H4A···O1i | 0.93 | 2.48 | 3.3823 (15) | 164.4 |
C4A—H4AA···O1ii | 0.93 | 2.51 | 3.3136 (15) | 145.1 |
C5B—H5BA···Cg1iii | 0.95 | 2.81 | 3.4504 (14) | 127 |
Symmetry codes: (i) −x+3, −y+2, −z+1; (ii) −x+2, −y+1, −z; (iii) −x+1, −y+1, −z+1. |
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Dithiocarbazate derivatives have been widely studied in radiopharmaceutical applications (Boschi et al. 2003) and have potential biological activity as anticancer and antimicrobial drugs (Bharti et al. 2000). This functional group is of particular interest and can coordinate to metals to give structures with different geometries and properties. As a part of our ongoing research on the dithio derivatives of acid hydrazides, we report here the crystal structure of the title compound, C20H118N2O2S2, a new bis benzyl sulfanyl methylene hydrazide.
The dihedral angle between the 2-furoic acid group and the two benzyl groups is 72.4 (9)° and 75.8 (8)°, respectively, while the angle between the mean planes of the two benzyl groups is 48.9 (2)° (Fig. 1). Bond angles around C1 clearly indicate planar sp2 behavior. Crystal packing is stabilized by intermolecular C—H···O packing interactions between the extended oxygen atom (O1) of a 2-furoic acid group and hydrogen atoms, both from nearby benzyl (H4AA) and 2-furoic acid groups (H4A) in the unit cell, which link the molecules into chains in a zigzag-like pattern, diagonally across the ac plane containing the 2-furoic acid rings (Fig. 2). Additional intermolecular interactions occur between the Cg1-π orbitals of one benzyl ring and hydrogen atoms from a nearby benzyl ring at the opposite end of the molecule (Table 1). Additional intramolecular interactions between the hydrazide hydrogen atom (H2A) and both the oxygen from a nearby furoic acid group and a sulfur atom from a close sulfanyl group provide added stability.