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The search for new tuberculostatics is an important issue due to the increasing resistance of Mycobacterium tuberculosis to existing agents and the resulting spread of the pathogen. Hetero­aryl­dithio­carbazic acid derivatives have shown potential tuberculostatic activity and investigations of the structural aspects of these compounds are thus of inter­est. Three new examples have been syn­the­sized. The structure of methyl 2-[amino­(pyridin-3-yl)methyl­idene]hy­dra­zine­carbodi­thio­ate, C8H10N4S2, at 293 K has monoclinic (P21/n) symmetry. It is of inter­est with respect to anti­bacterial properties. The structure displays N—H...N and N—H...S hydrogen bonding. The structure of N′-(pyrrolidine-1-carbono­thio­yl)picolinohydrazonamide, C11H15N5S, at 100 K has monoclinic (P21/n) symmetry and is also of inter­est with respect to anti­bacterial properties. The structure displays N—H...S hydrogen bonding. The structure of (Z)-methyl 2-[amino­(pyridin-2-yl)methyl­idene]-1-methyl­hydrazinecarbodi­thio­ate, C9H13N4S2, has triclinic (P\overline{1}) symmetry. The structure displays N—H...S hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205322961800284X/fn3253sup1.cif
Contains datablocks S1, S2, S3, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961800284X/fn3253S1sup3.hkl
Contains datablock S1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961800284X/fn3253S2sup2.hkl
Contains datablock S2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961800284X/fn3253S3sup4.hkl
Contains datablock S3

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961800284X/fn3253S1sup5.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961800284X/fn3253S2sup6.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961800284X/fn3253S3sup7.cml
Supplementary material

CCDC references: 1824482; 1824481; 1824480

Computing details top

Data collection: APEX2 (Bruker, 2009) for S1, S2; CrysAlis PRO (Rigaku OD, 2015) for S3. Cell refinement: SAINT-Plus (Bruker, 2009) for S1, S2; CrysAlis PRO (Rigaku OD, 2015) for S3. Data reduction: SAINT-Plus (Bruker, 2009) for S1, S2; CrysAlis PRO (Rigaku OD, 2015) for S3. For all structures, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).

N'-(Pyrrolidine-1-carbonothioyl)picolinohydrazonamide (S1) top
Crystal data top
C11H15N5SF(000) = 528
Mr = 249.34Dx = 1.356 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54178 Å
a = 11.4343 (10) ÅCell parameters from 9950 reflections
b = 7.7435 (7) Åθ = 3.2–72.6°
c = 14.5125 (12) ŵ = 2.24 mm1
β = 108.109 (2)°T = 100 K
V = 1221.31 (18) Å3Needle, colourless
Z = 40.95 × 0.20 × 0.20 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
2371 reflections with I > 2σ(I)
ω scanRint = 0.032
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
θmax = 72.6°, θmin = 4.3°
Tmin = 0.698, Tmax = 1.000h = 1314
14315 measured reflectionsk = 99
2403 independent reflectionsl = 1717
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.031H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.082 w = 1/[σ2(Fo2) + (0.0444P)2 + 0.5328P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
2403 reflectionsΔρmax = 0.26 e Å3
163 parametersΔρmin = 0.25 e Å3
Special details top

Geometry. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.87777 (11)0.30274 (15)0.60567 (9)0.0188 (2)
C40.76319 (11)0.37863 (15)0.79712 (8)0.0195 (3)
C120.92173 (12)0.27575 (18)0.44829 (9)0.0246 (3)
H12A0.93990.15310.45330.029*
H12B0.99840.34000.46640.029*
C130.84100 (13)0.32372 (19)0.34603 (9)0.0304 (3)
H13A0.89090.36200.30670.036*
H13B0.79140.22620.31450.036*
C140.76038 (12)0.46970 (18)0.36197 (8)0.0251 (3)
H14A0.80400.57890.37160.030*
H14B0.68570.48030.30750.030*
C150.73208 (11)0.41404 (17)0.45309 (8)0.0240 (3)
H15A0.71590.51300.48820.029*
H15B0.66180.33690.43780.029*
C410.81293 (11)0.35985 (15)0.90393 (8)0.0192 (2)
C420.74579 (11)0.40798 (16)0.96488 (9)0.0219 (3)
H420.66540.44790.93980.026*
C430.80202 (12)0.39482 (17)1.06441 (9)0.0245 (3)
H430.75990.42631.10730.029*
C440.92138 (12)0.33432 (18)1.09857 (9)0.0254 (3)
H440.96170.32631.16480.030*
C450.98018 (12)0.28551 (17)1.03183 (9)0.0251 (3)
H451.06000.24291.05530.030*
N20.79491 (9)0.35838 (14)0.64692 (7)0.0212 (2)
N30.83570 (10)0.34140 (14)0.74619 (7)0.0202 (2)
H30.9076 (16)0.305 (2)0.7743 (12)0.024*
N50.64763 (10)0.42894 (15)0.75213 (8)0.0241 (2)
H5A0.6312 (15)0.450 (2)0.6926 (13)0.029*
H5B0.6050 (15)0.483 (2)0.7829 (11)0.029*
N110.84526 (9)0.32455 (14)0.50907 (7)0.0209 (2)
N460.92821 (10)0.29664 (14)0.93607 (8)0.0227 (2)
S11.01620 (2)0.20426 (4)0.66657 (2)0.02183 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0167 (6)0.0216 (6)0.0177 (6)0.0022 (4)0.0047 (4)0.0000 (4)
C40.0197 (6)0.0204 (6)0.0183 (6)0.0012 (4)0.0056 (5)0.0018 (4)
C120.0240 (6)0.0332 (7)0.0194 (6)0.0015 (5)0.0109 (5)0.0021 (5)
C130.0347 (7)0.0399 (8)0.0173 (6)0.0039 (6)0.0093 (5)0.0024 (5)
C140.0249 (6)0.0316 (7)0.0164 (6)0.0066 (5)0.0031 (5)0.0026 (5)
C150.0205 (6)0.0319 (7)0.0185 (6)0.0021 (5)0.0044 (5)0.0046 (5)
C410.0190 (6)0.0217 (6)0.0169 (6)0.0018 (4)0.0055 (5)0.0006 (4)
C420.0210 (6)0.0244 (6)0.0211 (6)0.0025 (5)0.0077 (5)0.0010 (5)
C430.0283 (7)0.0278 (6)0.0205 (6)0.0023 (5)0.0124 (5)0.0005 (5)
C440.0273 (7)0.0331 (7)0.0154 (6)0.0002 (5)0.0062 (5)0.0011 (5)
C450.0197 (6)0.0362 (7)0.0189 (6)0.0032 (5)0.0051 (5)0.0028 (5)
N20.0196 (5)0.0294 (6)0.0138 (5)0.0028 (4)0.0042 (4)0.0007 (4)
N30.0175 (5)0.0278 (5)0.0143 (5)0.0023 (4)0.0033 (4)0.0008 (4)
N50.0205 (5)0.0349 (6)0.0159 (5)0.0047 (4)0.0041 (4)0.0027 (4)
N110.0188 (5)0.0287 (5)0.0159 (5)0.0021 (4)0.0064 (4)0.0008 (4)
N460.0193 (5)0.0312 (6)0.0182 (5)0.0018 (4)0.0066 (4)0.0004 (4)
S10.01313 (17)0.0324 (2)0.01973 (17)0.00018 (10)0.00472 (12)0.00331 (11)
Geometric parameters (Å, º) top
C1—N21.3395 (16)C14—C151.5183 (16)
C1—N111.3446 (15)C15—N111.4702 (15)
C1—S11.7316 (12)C41—N461.3462 (16)
C4—N31.3029 (16)C41—C421.3904 (16)
C4—N51.3371 (16)C42—C431.3903 (17)
C4—C411.4831 (16)C43—C441.3810 (19)
C12—N111.4714 (15)C44—C451.3921 (18)
C12—C131.5299 (18)C45—N461.3336 (16)
C13—C141.521 (2)N2—N31.3757 (13)
N2—C1—N11114.89 (10)C42—C41—C4122.04 (11)
N2—C1—S1125.09 (9)C43—C42—C41118.22 (11)
N11—C1—S1120.00 (9)C44—C43—C42118.96 (11)
N3—C4—N5119.60 (11)C43—C44—C45118.65 (11)
N3—C4—C41117.79 (11)N46—C45—C44123.53 (12)
N5—C4—C41122.59 (11)C1—N2—N3112.37 (10)
N11—C12—C13103.14 (10)C4—N3—N2120.30 (10)
C14—C13—C12104.15 (10)C1—N11—C15123.09 (10)
C15—C14—C13102.99 (10)C1—N11—C12124.72 (10)
N11—C15—C14103.05 (10)C15—N11—C12112.01 (10)
N46—C41—C42123.49 (11)C45—N46—C41117.11 (11)
N46—C41—C4114.45 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5B···S1i0.864 (17)2.456 (18)3.2895 (12)162.4 (14)
Symmetry code: (i) x+3/2, y+1/2, z+3/2.
Methyl 2-[amino(pyridin-3-yl)methylidene]hydrazinecarbodithioate (S2) top
Crystal data top
C8H10N4S2F(000) = 472
Mr = 226.32Dx = 1.443 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54178 Å
a = 7.2793 (9) ÅCell parameters from 9829 reflections
b = 19.962 (2) Åθ = 4.4–72.2°
c = 7.4299 (9) ŵ = 4.36 mm1
β = 105.205 (3)°T = 293 K
V = 1041.8 (2) Å3Needle, colourless
Z = 40.55 × 0.40 × 0.20 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
2043 reflections with I > 2σ(I)
ω scanRint = 0.042
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
θmax = 72.3°, θmin = 4.4°
Tmin = 0.447, Tmax = 0.754h = 88
2048 measured reflectionsk = 024
2048 independent reflectionsl = 09
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.031H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.087 w = 1/[σ2(Fo2) + (0.0506P)2 + 0.1572P]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max < 0.001
2048 reflectionsΔρmax = 0.27 e Å3
138 parametersΔρmin = 0.21 e Å3
Special details top

Geometry. 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.

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.7390 (2)0.13619 (8)0.1568 (2)0.0350 (3)
S10.79198 (7)0.08918 (2)0.36434 (6)0.04270 (15)
N20.7206 (2)0.20114 (7)0.18404 (18)0.0361 (3)
H20.718 (3)0.2295 (11)0.099 (3)0.043*
S20.70782 (7)0.10364 (2)0.05725 (6)0.04823 (16)
N30.7569 (2)0.22656 (7)0.36600 (17)0.0362 (3)
C40.6734 (2)0.28284 (7)0.3798 (2)0.0320 (3)
N50.5633 (2)0.32035 (8)0.2418 (2)0.0403 (3)
H5A0.523 (3)0.3024 (11)0.137 (3)0.048*
H5B0.497 (3)0.3471 (11)0.277 (3)0.048*
C110.8024 (4)0.00555 (9)0.2782 (3)0.0665 (6)
H11A0.68010.00660.19920.100*
H11B0.83680.02500.38130.100*
H11C0.89580.00360.20800.100*
C410.7107 (2)0.31150 (7)0.5706 (2)0.0314 (3)
C420.7574 (2)0.37836 (8)0.6060 (2)0.0391 (3)
H420.76080.40730.50890.047*
C430.7989 (3)0.40134 (8)0.7878 (3)0.0445 (4)
H430.83140.44590.81530.053*
C440.7910 (3)0.35686 (9)0.9274 (2)0.0423 (4)
H440.82340.37211.05000.051*
C460.6995 (2)0.27098 (8)0.7191 (2)0.0360 (3)
H460.66280.22650.69510.043*
N460.7392 (2)0.29294 (7)0.89501 (18)0.0411 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0386 (7)0.0321 (7)0.0337 (8)0.0032 (6)0.0088 (6)0.0000 (6)
S10.0587 (3)0.0294 (2)0.0357 (2)0.00187 (16)0.00467 (18)0.00298 (14)
N20.0542 (8)0.0293 (6)0.0240 (6)0.0020 (5)0.0090 (5)0.0013 (5)
S20.0678 (3)0.0423 (2)0.0351 (2)0.01047 (19)0.0145 (2)0.01018 (16)
N30.0522 (7)0.0317 (6)0.0235 (6)0.0036 (5)0.0081 (5)0.0011 (5)
C40.0407 (7)0.0308 (7)0.0248 (7)0.0008 (6)0.0092 (6)0.0043 (5)
N50.0520 (8)0.0401 (8)0.0262 (6)0.0105 (6)0.0057 (6)0.0022 (5)
C110.0988 (17)0.0297 (9)0.0627 (13)0.0025 (10)0.0066 (12)0.0003 (9)
C410.0371 (7)0.0310 (7)0.0257 (7)0.0041 (6)0.0077 (5)0.0020 (6)
C420.0509 (9)0.0328 (8)0.0345 (8)0.0004 (6)0.0126 (7)0.0046 (6)
C430.0558 (10)0.0335 (8)0.0452 (10)0.0055 (7)0.0149 (8)0.0068 (7)
C440.0546 (9)0.0423 (9)0.0300 (8)0.0014 (7)0.0109 (7)0.0075 (6)
C460.0495 (8)0.0314 (7)0.0277 (7)0.0013 (6)0.0109 (6)0.0007 (6)
N460.0593 (8)0.0378 (7)0.0274 (6)0.0034 (6)0.0135 (6)0.0017 (5)
Geometric parameters (Å, º) top
C1—N21.324 (2)C11—H11B0.9600
C1—S21.6775 (15)C11—H11C0.9600
C1—S11.7592 (15)C41—C421.385 (2)
S1—C111.797 (2)C41—C461.388 (2)
N2—N31.4027 (17)C42—C431.383 (2)
N2—H20.85 (2)C42—H420.9300
N3—C41.294 (2)C43—C441.378 (3)
C4—N51.350 (2)C43—H430.9300
C4—C411.486 (2)C44—N461.334 (2)
N5—H5A0.84 (2)C44—H440.9300
N5—H5B0.81 (2)C46—N461.337 (2)
C11—H11A0.9600C46—H460.9300
N2—C1—S2122.01 (12)H11A—C11—H11C109.5
N2—C1—S1113.32 (11)H11B—C11—H11C109.5
S2—C1—S1124.65 (9)C42—C41—C46118.26 (14)
C1—S1—C11101.73 (9)C42—C41—C4121.76 (13)
C1—N2—N3120.02 (13)C46—C41—C4119.99 (13)
C1—N2—H2121.5 (14)C43—C42—C41119.00 (15)
N3—N2—H2116.2 (14)C43—C42—H42120.5
C4—N3—N2114.62 (13)C41—C42—H42120.5
N3—C4—N5128.24 (15)C44—C43—C42118.69 (15)
N3—C4—C41115.95 (13)C44—C43—H43120.7
N5—C4—C41115.74 (13)C42—C43—H43120.7
C4—N5—H5A117.6 (15)N46—C44—C43123.09 (15)
C4—N5—H5B114.2 (16)N46—C44—H44118.5
H5A—N5—H5B119 (2)C43—C44—H44118.5
S1—C11—H11A109.5N46—C46—C41122.94 (14)
S1—C11—H11B109.5N46—C46—H46118.5
H11A—C11—H11B109.5C41—C46—H46118.5
S1—C11—H11C109.5C44—N46—C46117.93 (14)
N2—C1—S1—C11178.98 (14)N5—C4—C41—C46136.20 (15)
S2—C1—S1—C110.58 (15)C46—C41—C42—C432.7 (2)
S2—C1—N2—N3176.93 (11)C4—C41—C42—C43177.11 (15)
S1—C1—N2—N34.62 (19)C41—C42—C43—C440.4 (3)
C1—N2—N3—C4156.50 (15)C42—C43—C44—N462.2 (3)
N2—N3—C4—N52.6 (2)C42—C41—C46—N462.8 (2)
N2—N3—C4—C41179.36 (12)C4—C41—C46—N46177.10 (14)
N3—C4—C41—C42133.26 (16)C43—C44—N46—C462.3 (3)
N5—C4—C41—C4243.9 (2)C41—C46—N46—C440.2 (2)
N3—C4—C41—C4646.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···N3i0.84 (2)2.47 (2)3.222 (2)150.2 (19)
N5—H5B···S2ii0.81 (2)2.88 (2)3.6405 (17)158.6 (19)
N2—H2···N46iii0.85 (2)2.01 (2)2.853 (2)174.1 (19)
Symmetry codes: (i) x1/2, y+1/2, z1/2; (ii) x1/2, y+1/2, z+1/2; (iii) x, y, z1.
(Z)-Methyl 2-[amino(pyridin-2-yl)methylidene]-1-methylhydrazinecarbodithioate (S3) top
Crystal data top
C9H12N4S2Z = 2
Mr = 240.35F(000) = 252
Triclinic, P1Dx = 1.362 Mg m3
a = 7.3230 (2) ÅCu Kα radiation, λ = 1.54184 Å
b = 8.5983 (2) ÅCell parameters from 21672 reflections
c = 10.0343 (2) Åθ = 4.7–78.7°
α = 79.167 (2)°µ = 3.91 mm1
β = 71.019 (2)°T = 100 K
γ = 84.080 (2)°Needle, colourless
V = 586.21 (3) Å30.50 × 0.40 × 0.15 mm
Data collection top
XtaLAB Synergy, Dualflex, Pilatus 300K
diffractometer
2417 independent reflections
Radiation source: micro-focus sealed X-ray tube2393 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.060
ω scansθmax = 79.0°, θmin = 4.7°
Absorption correction: gaussian
(CrysAlis PRO; Rigaku OD, 2015)
h = 99
Tmin = 0.176, Tmax = 1.000k = 1010
24172 measured reflectionsl = 1212
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.035 w = 1/[σ2(Fo2) + (0.0656P)2 + 0.309P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.099(Δ/σ)max = 0.001
S = 1.04Δρmax = 0.56 e Å3
2417 reflectionsΔρmin = 0.30 e Å3
145 parametersExtinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0147 (15)
Special details top

Geometry. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.31630 (19)0.09177 (17)0.72264 (15)0.0122 (3)
S10.34397 (5)0.06346 (4)0.89411 (4)0.01573 (15)
C20.3910 (2)0.27722 (18)0.49557 (16)0.0171 (3)
H2A0.40590.19100.44390.026*
H2B0.48920.35160.44430.026*
H2C0.26580.32910.50560.026*
N20.40933 (17)0.21624 (15)0.63707 (13)0.0135 (3)
S20.18763 (5)0.02514 (4)0.67422 (4)0.01568 (15)
N30.47965 (17)0.32513 (15)0.69812 (13)0.0144 (3)
C40.6665 (2)0.30834 (17)0.67435 (15)0.0130 (3)
N50.7889 (2)0.20436 (17)0.60358 (15)0.0204 (3)
H5A0.752 (3)0.133 (3)0.569 (2)0.024*
H5B0.899 (3)0.199 (3)0.603 (2)0.024*
C110.2272 (2)0.11904 (19)0.97915 (17)0.0211 (3)
H11A0.09660.10930.97640.032*
H11B0.22640.14201.07670.032*
H11C0.29600.20340.92990.032*
C410.7511 (2)0.41881 (16)0.73531 (15)0.0124 (3)
N420.94248 (18)0.40172 (16)0.70950 (15)0.0190 (3)
C431.0231 (2)0.4971 (2)0.76351 (19)0.0229 (4)
H431.15600.48640.74700.027*
C440.9187 (2)0.6113 (2)0.84294 (18)0.0220 (3)
H440.98030.67560.87840.026*
C450.7210 (2)0.6273 (2)0.86809 (18)0.0219 (3)
H450.64730.70300.92060.026*
C460.6342 (2)0.52893 (19)0.81397 (16)0.0177 (3)
H460.50150.53650.82990.021*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0091 (6)0.0145 (7)0.0155 (7)0.0010 (5)0.0050 (5)0.0071 (5)
S10.0181 (2)0.0174 (2)0.0156 (2)0.00557 (14)0.00900 (15)0.00283 (15)
C20.0170 (7)0.0195 (8)0.0162 (7)0.0027 (6)0.0067 (5)0.0029 (6)
N20.0131 (6)0.0136 (6)0.0166 (6)0.0027 (4)0.0067 (5)0.0046 (5)
S20.0159 (2)0.0162 (2)0.0195 (2)0.00468 (14)0.00815 (15)0.00725 (15)
N30.0127 (6)0.0137 (6)0.0200 (6)0.0032 (4)0.0065 (5)0.0065 (5)
C40.0146 (7)0.0122 (7)0.0135 (6)0.0019 (5)0.0060 (5)0.0020 (5)
N50.0130 (6)0.0253 (7)0.0298 (7)0.0014 (5)0.0091 (5)0.0181 (6)
C110.0237 (8)0.0178 (8)0.0230 (8)0.0058 (6)0.0106 (6)0.0021 (6)
C410.0139 (7)0.0108 (7)0.0138 (6)0.0030 (5)0.0059 (5)0.0010 (5)
N420.0140 (6)0.0181 (6)0.0277 (7)0.0016 (5)0.0070 (5)0.0094 (5)
C430.0152 (7)0.0233 (8)0.0354 (9)0.0039 (6)0.0101 (6)0.0116 (7)
C440.0227 (8)0.0208 (8)0.0286 (8)0.0064 (6)0.0114 (6)0.0100 (6)
C450.0222 (8)0.0211 (8)0.0268 (8)0.0008 (6)0.0081 (6)0.0136 (6)
C460.0147 (7)0.0203 (8)0.0207 (7)0.0011 (6)0.0060 (5)0.0088 (6)
Geometric parameters (Å, º) top
C1—N21.331 (2)C11—H11A0.9600
C1—S21.6767 (14)C11—H11B0.9600
C1—S11.7663 (14)C11—H11C0.9600
S1—C111.7947 (16)C41—N421.3373 (19)
C2—N21.4626 (19)C41—C461.388 (2)
C2—H2A0.9600N42—C431.338 (2)
C2—H2B0.9600C43—C441.388 (2)
C2—H2C0.9600C43—H430.9300
N2—N31.4273 (17)C44—C451.383 (2)
N3—C41.3073 (19)C44—H440.9300
C4—N51.3292 (19)C45—C461.387 (2)
C4—C411.4991 (19)C45—H450.9300
N5—H5A0.86 (2)C46—H460.9300
N5—H5B0.80 (2)
N2—C1—S2124.23 (11)S1—C11—H11B109.5
N2—C1—S1112.10 (10)H11A—C11—H11B109.5
S2—C1—S1123.67 (9)S1—C11—H11C109.5
C1—S1—C11102.69 (7)H11A—C11—H11C109.5
N2—C2—H2A109.5H11B—C11—H11C109.5
N2—C2—H2B109.5N42—C41—C46123.67 (13)
H2A—C2—H2B109.5N42—C41—C4115.47 (12)
N2—C2—H2C109.5C46—C41—C4120.85 (13)
H2A—C2—H2C109.5C41—N42—C43117.22 (13)
H2B—C2—H2C109.5N42—C43—C44123.42 (15)
C1—N2—N3118.75 (12)N42—C43—H43118.3
C1—N2—C2123.12 (12)C44—C43—H43118.3
N3—N2—C2115.15 (12)C45—C44—C43118.43 (14)
C4—N3—N2112.75 (11)C45—C44—H44120.8
N3—C4—N5127.57 (14)C43—C44—H44120.8
N3—C4—C41115.85 (12)C44—C45—C46119.14 (14)
N5—C4—C41116.57 (13)C44—C45—H45120.4
C4—N5—H5A122.6 (14)C46—C45—H45120.4
C4—N5—H5B118.5 (15)C45—C46—C41118.12 (14)
H5A—N5—H5B118 (2)C45—C46—H46120.9
S1—C11—H11A109.5C41—C46—H46120.9
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5B···S2i0.80 (2)2.88 (2)3.5431 (14)141.3 (19)
N5—H5A···S2ii0.86 (2)2.66 (2)3.3798 (14)141.5 (18)
Symmetry codes: (i) x+1, y, z; (ii) x+1, y, z+1.
The antimicrobial activity of compounds P1P4 and S1-S3 against Gram-positive bacteria [MIC (MBC) (µg ml-1) values] top
CompoundS. aureus ATCC 25923S. aureus ATCC 6538S. aureus ATCC 43300S. epidermidis ATCC 12228M. luteus ATCC 10240B. subtilis ATCC 6633B. cereus ATCC 10876S. pyogenes ATCC 19615S. pneumoniae ATCC 49619S. mutans ATCC 25175
P1>1000>1000>10001000>1000>1000
P21000 (>1000)500 (>1000)500 (>1000)>1000 (>1000)>1000 (>1000)1000 (>1000)>1000 (>1000)250 (>1000)>1000 (>1000)250 (>1000)
P30.49 (7.9)3.9 (31.25)0.49 (0.49)0.49 (15.6)0.98 (7.8)0.49 (0.49)0.98 (3.9)15.6 (62.5)125 (250)7.8 (62.5)
P40.98 (1.95)1.95 (15.6)0.98 (15.6)0.98 (15.6)1.95 (1.95)1.95 (1.95)0.98 (0.98)31.25 (62.5)15.6 (62.5)7.8 (31.25)
S11.95 (125)7.8 (250)7.8 (250)7.8 (62.5)1.95 (3.9)7.8 (250)7.8 (250)15.6 (500)125 (250)125 (125)
S2125 (500)500 (500)500 (500)250 (500)125 (250)250 (1000)250 (>1000)250 (500)500 (500)250 (250)
S3>1000>1000>1000>1000>1000>1000>1000>1000>1000>1000
Vancomicin0.98 (7.81)0.49 (1.95)0.49 (1.95)0.98 (0.98)0.12 (0.12)0.24 (0.49)0.98 (15.6)0.24 (0.49)0.24 (0.49)0.98 (0.98)
Ciprofloxacin0.49 (0.49)0.24 (0.24)0.24 (0.24)0.49 (0.49)0.98 (1.95)0.03 (0.12)0.12 (0.12)
 

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