Planarity of hetero­aryl­dithio­carbazic acid derivatives showing tuberculostatic activity: structure–activity relationships

Szczesio, M.; Gołka, J.; Korona-Głowniak, I.; Orlewska, C.; Gobis, K.; Olczak, A.

doi:10.1107/S205322961800284X

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Planarity of heteroaryldithiocarbazic acid derivatives showing tuberculostatic activity: structure–activity relationships

M. Szczesio, J. Gołka, I. Korona-Głowniak, C. Orlewska, K. Gobis and A. Olczak

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.

Keywords: antibacterial activity; structure–activity relationship; crystal structure; Mycobacterium tuberculosis; tuberculostatic; heteroaryldithiocarbazic acid.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S205322961800284X/fn3253sup1.cif Contains datablocks S1, S2, S3, global
	Structure factor file (CIF format) https://doi.org/10.1107/S205322961800284X/fn3253S1sup3.hkl Contains datablock S1
	Structure factor file (CIF format) https://doi.org/10.1107/S205322961800284X/fn3253S2sup2.hkl Contains datablock S2
	Structure factor file (CIF format) https://doi.org/10.1107/S205322961800284X/fn3253S3sup4.hkl Contains datablock S3
	Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961800284X/fn3253S1sup5.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961800284X/fn3253S2sup6.cml Supplementary material
	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

C₁₁H₁₅N₅S	F(000) = 528
M_r = 249.34	D_x = 1.356 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
a = 11.4343 (10) Å	Cell parameters from 9950 reflections
b = 7.7435 (7) Å	θ = 3.2–72.6°
c = 14.5125 (12) Å	µ = 2.24 mm⁻¹
β = 108.109 (2)°	T = 100 K
V = 1221.31 (18) Å³	Needle, colourless
Z = 4	0.95 × 0.20 × 0.20 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	2371 reflections with I > 2σ(I)
ω scan	R_int = 0.032
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	θ_max = 72.6°, θ_min = 4.3°
T_min = 0.698, T_max = 1.000	h = −13→14
14315 measured reflections	k = −9→9
2403 independent reflections	l = −17→17

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.082	w = 1/[σ²(F_o²) + (0.0444P)² + 0.5328P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
2403 reflections	Δρ_max = 0.26 e Å⁻³
163 parameters	Δρ_min = −0.25 e Å⁻³

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

	x	y	z	U_iso*/U_eq
C1	0.87777 (11)	0.30274 (15)	0.60567 (9)	0.0188 (2)
C4	0.76319 (11)	0.37863 (15)	0.79712 (8)	0.0195 (3)
C12	0.92173 (12)	0.27575 (18)	0.44829 (9)	0.0246 (3)
H12A	0.9399	0.1531	0.4533	0.029*
H12B	0.9984	0.3400	0.4664	0.029*
C13	0.84100 (13)	0.32372 (19)	0.34603 (9)	0.0304 (3)
H13A	0.8909	0.3620	0.3067	0.036*
H13B	0.7914	0.2262	0.3145	0.036*
C14	0.76038 (12)	0.46970 (18)	0.36197 (8)	0.0251 (3)
H14A	0.8040	0.5789	0.3716	0.030*
H14B	0.6857	0.4803	0.3075	0.030*
C15	0.73208 (11)	0.41404 (17)	0.45309 (8)	0.0240 (3)
H15A	0.7159	0.5130	0.4882	0.029*
H15B	0.6618	0.3369	0.4378	0.029*
C41	0.81293 (11)	0.35985 (15)	0.90393 (8)	0.0192 (2)
C42	0.74579 (11)	0.40798 (16)	0.96488 (9)	0.0219 (3)
H42	0.6654	0.4479	0.9398	0.026*
C43	0.80202 (12)	0.39482 (17)	1.06441 (9)	0.0245 (3)
H43	0.7599	0.4263	1.1073	0.029*
C44	0.92138 (12)	0.33432 (18)	1.09857 (9)	0.0254 (3)
H44	0.9617	0.3263	1.1648	0.030*
C45	0.98018 (12)	0.28551 (17)	1.03183 (9)	0.0251 (3)
H45	1.0600	0.2429	1.0553	0.030*
N2	0.79491 (9)	0.35838 (14)	0.64692 (7)	0.0212 (2)
N3	0.83570 (10)	0.34140 (14)	0.74619 (7)	0.0202 (2)
H3	0.9076 (16)	0.305 (2)	0.7743 (12)	0.024*
N5	0.64763 (10)	0.42894 (15)	0.75213 (8)	0.0241 (2)
H5A	0.6312 (15)	0.450 (2)	0.6926 (13)	0.029*
H5B	0.6050 (15)	0.483 (2)	0.7829 (11)	0.029*
N11	0.84526 (9)	0.32455 (14)	0.50907 (7)	0.0209 (2)
N46	0.92821 (10)	0.29664 (14)	0.93607 (8)	0.0227 (2)
S1	1.01620 (2)	0.20426 (4)	0.66657 (2)	0.02183 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0167 (6)	0.0216 (6)	0.0177 (6)	−0.0022 (4)	0.0047 (4)	0.0000 (4)
C4	0.0197 (6)	0.0204 (6)	0.0183 (6)	−0.0012 (4)	0.0056 (5)	−0.0018 (4)
C12	0.0240 (6)	0.0332 (7)	0.0194 (6)	−0.0015 (5)	0.0109 (5)	−0.0021 (5)
C13	0.0347 (7)	0.0399 (8)	0.0173 (6)	−0.0039 (6)	0.0093 (5)	−0.0024 (5)
C14	0.0249 (6)	0.0316 (7)	0.0164 (6)	−0.0066 (5)	0.0031 (5)	0.0026 (5)
C15	0.0205 (6)	0.0319 (7)	0.0185 (6)	0.0021 (5)	0.0044 (5)	0.0046 (5)
C41	0.0190 (6)	0.0217 (6)	0.0169 (6)	−0.0018 (4)	0.0055 (5)	−0.0006 (4)
C42	0.0210 (6)	0.0244 (6)	0.0211 (6)	0.0025 (5)	0.0077 (5)	0.0010 (5)
C43	0.0283 (7)	0.0278 (6)	0.0205 (6)	0.0023 (5)	0.0124 (5)	−0.0005 (5)
C44	0.0273 (7)	0.0331 (7)	0.0154 (6)	0.0002 (5)	0.0062 (5)	0.0011 (5)
C45	0.0197 (6)	0.0362 (7)	0.0189 (6)	0.0032 (5)	0.0051 (5)	0.0028 (5)
N2	0.0196 (5)	0.0294 (6)	0.0138 (5)	0.0028 (4)	0.0042 (4)	0.0007 (4)
N3	0.0175 (5)	0.0278 (5)	0.0143 (5)	0.0023 (4)	0.0033 (4)	0.0008 (4)
N5	0.0205 (5)	0.0349 (6)	0.0159 (5)	0.0047 (4)	0.0041 (4)	−0.0027 (4)
N11	0.0188 (5)	0.0287 (5)	0.0159 (5)	0.0021 (4)	0.0064 (4)	0.0008 (4)
N46	0.0193 (5)	0.0312 (6)	0.0182 (5)	0.0018 (4)	0.0066 (4)	0.0004 (4)
S1	0.01313 (17)	0.0324 (2)	0.01973 (17)	0.00018 (10)	0.00472 (12)	0.00331 (11)

Geometric parameters (Å, º) top

C1—N2	1.3395 (16)	C14—C15	1.5183 (16)
C1—N11	1.3446 (15)	C15—N11	1.4702 (15)
C1—S1	1.7316 (12)	C41—N46	1.3462 (16)
C4—N3	1.3029 (16)	C41—C42	1.3904 (16)
C4—N5	1.3371 (16)	C42—C43	1.3903 (17)
C4—C41	1.4831 (16)	C43—C44	1.3810 (19)
C12—N11	1.4714 (15)	C44—C45	1.3921 (18)
C12—C13	1.5299 (18)	C45—N46	1.3336 (16)
C13—C14	1.521 (2)	N2—N3	1.3757 (13)

N2—C1—N11	114.89 (10)	C42—C41—C4	122.04 (11)
N2—C1—S1	125.09 (9)	C43—C42—C41	118.22 (11)
N11—C1—S1	120.00 (9)	C44—C43—C42	118.96 (11)
N3—C4—N5	119.60 (11)	C43—C44—C45	118.65 (11)
N3—C4—C41	117.79 (11)	N46—C45—C44	123.53 (12)
N5—C4—C41	122.59 (11)	C1—N2—N3	112.37 (10)
N11—C12—C13	103.14 (10)	C4—N3—N2	120.30 (10)
C14—C13—C12	104.15 (10)	C1—N11—C15	123.09 (10)
C15—C14—C13	102.99 (10)	C1—N11—C12	124.72 (10)
N11—C15—C14	103.05 (10)	C15—N11—C12	112.01 (10)
N46—C41—C42	123.49 (11)	C45—N46—C41	117.11 (11)
N46—C41—C4	114.45 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5B···S1ⁱ	0.864 (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

C₈H₁₀N₄S₂	F(000) = 472
M_r = 226.32	D_x = 1.443 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
a = 7.2793 (9) Å	Cell parameters from 9829 reflections
b = 19.962 (2) Å	θ = 4.4–72.2°
c = 7.4299 (9) Å	µ = 4.36 mm⁻¹
β = 105.205 (3)°	T = 293 K
V = 1041.8 (2) Å³	Needle, colourless
Z = 4	0.55 × 0.40 × 0.20 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	2043 reflections with I > 2σ(I)
ω scan	R_int = 0.042
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	θ_max = 72.3°, θ_min = 4.4°
T_min = 0.447, T_max = 0.754	h = −8→8
2048 measured reflections	k = 0→24
2048 independent reflections	l = 0→9

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.087	w = 1/[σ²(F_o²) + (0.0506P)² + 0.1572P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max < 0.001
2048 reflections	Δρ_max = 0.27 e Å⁻³
138 parameters	Δρ_min = −0.21 e Å⁻³

Special details top

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.7390 (2)	0.13619 (8)	0.1568 (2)	0.0350 (3)
S1	0.79198 (7)	0.08918 (2)	0.36434 (6)	0.04270 (15)
N2	0.7206 (2)	0.20114 (7)	0.18404 (18)	0.0361 (3)
H2	0.718 (3)	0.2295 (11)	0.099 (3)	0.043*
S2	0.70782 (7)	0.10364 (2)	−0.05725 (6)	0.04823 (16)
N3	0.7569 (2)	0.22656 (7)	0.36600 (17)	0.0362 (3)
C4	0.6734 (2)	0.28284 (7)	0.3798 (2)	0.0320 (3)
N5	0.5633 (2)	0.32035 (8)	0.2418 (2)	0.0403 (3)
H5A	0.523 (3)	0.3024 (11)	0.137 (3)	0.048*
H5B	0.497 (3)	0.3471 (11)	0.277 (3)	0.048*
C11	0.8024 (4)	0.00555 (9)	0.2782 (3)	0.0665 (6)
H11A	0.6801	−0.0066	0.1992	0.100*
H11B	0.8368	−0.0250	0.3813	0.100*
H11C	0.8958	0.0036	0.2080	0.100*
C41	0.7107 (2)	0.31150 (7)	0.5706 (2)	0.0314 (3)
C42	0.7574 (2)	0.37836 (8)	0.6060 (2)	0.0391 (3)
H42	0.7608	0.4073	0.5089	0.047*
C43	0.7989 (3)	0.40134 (8)	0.7878 (3)	0.0445 (4)
H43	0.8314	0.4459	0.8153	0.053*
C44	0.7910 (3)	0.35686 (9)	0.9274 (2)	0.0423 (4)
H44	0.8234	0.3721	1.0500	0.051*
C46	0.6995 (2)	0.27098 (8)	0.7191 (2)	0.0360 (3)
H46	0.6628	0.2265	0.6951	0.043*
N46	0.7392 (2)	0.29294 (7)	0.89501 (18)	0.0411 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0386 (7)	0.0321 (7)	0.0337 (8)	−0.0032 (6)	0.0088 (6)	0.0000 (6)
S1	0.0587 (3)	0.0294 (2)	0.0357 (2)	−0.00187 (16)	0.00467 (18)	0.00298 (14)
N2	0.0542 (8)	0.0293 (6)	0.0240 (6)	0.0020 (5)	0.0090 (5)	0.0013 (5)
S2	0.0678 (3)	0.0423 (2)	0.0351 (2)	−0.01047 (19)	0.0145 (2)	−0.01018 (16)
N3	0.0522 (7)	0.0317 (6)	0.0235 (6)	0.0036 (5)	0.0081 (5)	0.0011 (5)
C4	0.0407 (7)	0.0308 (7)	0.0248 (7)	−0.0008 (6)	0.0092 (6)	0.0043 (5)
N5	0.0520 (8)	0.0401 (8)	0.0262 (6)	0.0105 (6)	0.0057 (6)	0.0022 (5)
C11	0.0988 (17)	0.0297 (9)	0.0627 (13)	−0.0025 (10)	0.0066 (12)	0.0003 (9)
C41	0.0371 (7)	0.0310 (7)	0.0257 (7)	0.0041 (6)	0.0077 (5)	0.0020 (6)
C42	0.0509 (9)	0.0328 (8)	0.0345 (8)	0.0004 (6)	0.0126 (7)	0.0046 (6)
C43	0.0558 (10)	0.0335 (8)	0.0452 (10)	−0.0055 (7)	0.0149 (8)	−0.0068 (7)
C44	0.0546 (9)	0.0423 (9)	0.0300 (8)	0.0014 (7)	0.0109 (7)	−0.0075 (6)
C46	0.0495 (8)	0.0314 (7)	0.0277 (7)	0.0013 (6)	0.0109 (6)	0.0007 (6)
N46	0.0593 (8)	0.0378 (7)	0.0274 (6)	0.0034 (6)	0.0135 (6)	0.0017 (5)

Geometric parameters (Å, º) top

C1—N2	1.324 (2)	C11—H11B	0.9600
C1—S2	1.6775 (15)	C11—H11C	0.9600
C1—S1	1.7592 (15)	C41—C42	1.385 (2)
S1—C11	1.797 (2)	C41—C46	1.388 (2)
N2—N3	1.4027 (17)	C42—C43	1.383 (2)
N2—H2	0.85 (2)	C42—H42	0.9300
N3—C4	1.294 (2)	C43—C44	1.378 (3)
C4—N5	1.350 (2)	C43—H43	0.9300
C4—C41	1.486 (2)	C44—N46	1.334 (2)
N5—H5A	0.84 (2)	C44—H44	0.9300
N5—H5B	0.81 (2)	C46—N46	1.337 (2)
C11—H11A	0.9600	C46—H46	0.9300

N2—C1—S2	122.01 (12)	H11A—C11—H11C	109.5
N2—C1—S1	113.32 (11)	H11B—C11—H11C	109.5
S2—C1—S1	124.65 (9)	C42—C41—C46	118.26 (14)
C1—S1—C11	101.73 (9)	C42—C41—C4	121.76 (13)
C1—N2—N3	120.02 (13)	C46—C41—C4	119.99 (13)
C1—N2—H2	121.5 (14)	C43—C42—C41	119.00 (15)
N3—N2—H2	116.2 (14)	C43—C42—H42	120.5
C4—N3—N2	114.62 (13)	C41—C42—H42	120.5
N3—C4—N5	128.24 (15)	C44—C43—C42	118.69 (15)
N3—C4—C41	115.95 (13)	C44—C43—H43	120.7
N5—C4—C41	115.74 (13)	C42—C43—H43	120.7
C4—N5—H5A	117.6 (15)	N46—C44—C43	123.09 (15)
C4—N5—H5B	114.2 (16)	N46—C44—H44	118.5
H5A—N5—H5B	119 (2)	C43—C44—H44	118.5
S1—C11—H11A	109.5	N46—C46—C41	122.94 (14)
S1—C11—H11B	109.5	N46—C46—H46	118.5
H11A—C11—H11B	109.5	C41—C46—H46	118.5
S1—C11—H11C	109.5	C44—N46—C46	117.93 (14)

N2—C1—S1—C11	178.98 (14)	N5—C4—C41—C46	136.20 (15)
S2—C1—S1—C11	0.58 (15)	C46—C41—C42—C43	2.7 (2)
S2—C1—N2—N3	−176.93 (11)	C4—C41—C42—C43	−177.11 (15)
S1—C1—N2—N3	4.62 (19)	C41—C42—C43—C44	−0.4 (3)
C1—N2—N3—C4	−156.50 (15)	C42—C43—C44—N46	−2.2 (3)
N2—N3—C4—N5	−2.6 (2)	C42—C41—C46—N46	−2.8 (2)
N2—N3—C4—C41	−179.36 (12)	C4—C41—C46—N46	177.10 (14)
N3—C4—C41—C42	133.26 (16)	C43—C44—N46—C46	2.3 (3)
N5—C4—C41—C42	−43.9 (2)	C41—C46—N46—C44	0.2 (2)
N3—C4—C41—C46	−46.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5A···N3ⁱ	0.84 (2)	2.47 (2)	3.222 (2)	150.2 (19)
N5—H5B···S2ⁱⁱ	0.81 (2)	2.88 (2)	3.6405 (17)	158.6 (19)
N2—H2···N46ⁱⁱⁱ	0.85 (2)	2.01 (2)	2.853 (2)	174.1 (19)

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x−1/2, −y+1/2, z+1/2; (iii) x, y, z−1.

(Z)-Methyl 2-[amino(pyridin-2-yl)methylidene]-1-methylhydrazinecarbodithioate (S3) top

Crystal data top

C₉H₁₂N₄S₂	Z = 2
M_r = 240.35	F(000) = 252
Triclinic, P1	D_x = 1.362 Mg m⁻³
a = 7.3230 (2) Å	Cu Kα radiation, λ = 1.54184 Å
b = 8.5983 (2) Å	Cell parameters from 21672 reflections
c = 10.0343 (2) Å	θ = 4.7–78.7°
α = 79.167 (2)°	µ = 3.91 mm⁻¹
β = 71.019 (2)°	T = 100 K
γ = 84.080 (2)°	Needle, colourless
V = 586.21 (3) Å³	0.50 × 0.40 × 0.15 mm

Data collection top

XtaLAB Synergy, Dualflex, Pilatus 300K diffractometer	2417 independent reflections
Radiation source: micro-focus sealed X-ray tube	2393 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.060
ω scans	θ_max = 79.0°, θ_min = 4.7°
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2015)	h = −9→9
T_min = 0.176, T_max = 1.000	k = −10→10
24172 measured reflections	l = −12→12

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.035	w = 1/[σ²(F_o²) + (0.0656P)² + 0.309P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.099	(Δ/σ)_max = 0.001
S = 1.04	Δρ_max = 0.56 e Å⁻³
2417 reflections	Δρ_min = −0.30 e Å⁻³
145 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0147 (15)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.31630 (19)	0.09177 (17)	0.72264 (15)	0.0122 (3)
S1	0.34397 (5)	0.06346 (4)	0.89411 (4)	0.01573 (15)
C2	0.3910 (2)	0.27722 (18)	0.49557 (16)	0.0171 (3)
H2A	0.4059	0.1910	0.4439	0.026*
H2B	0.4892	0.3516	0.4443	0.026*
H2C	0.2658	0.3291	0.5056	0.026*
N2	0.40933 (17)	0.21624 (15)	0.63707 (13)	0.0135 (3)
S2	0.18763 (5)	−0.02514 (4)	0.67422 (4)	0.01568 (15)
N3	0.47965 (17)	0.32513 (15)	0.69812 (13)	0.0144 (3)
C4	0.6665 (2)	0.30834 (17)	0.67435 (15)	0.0130 (3)
N5	0.7889 (2)	0.20436 (17)	0.60358 (15)	0.0204 (3)
H5A	0.752 (3)	0.133 (3)	0.569 (2)	0.024*
H5B	0.899 (3)	0.199 (3)	0.603 (2)	0.024*
C11	0.2272 (2)	−0.11904 (19)	0.97915 (17)	0.0211 (3)
H11A	0.0966	−0.1093	0.9764	0.032*
H11B	0.2264	−0.1420	1.0767	0.032*
H11C	0.2960	−0.2034	0.9299	0.032*
C41	0.7511 (2)	0.41881 (16)	0.73531 (15)	0.0124 (3)
N42	0.94248 (18)	0.40172 (16)	0.70950 (15)	0.0190 (3)
C43	1.0231 (2)	0.4971 (2)	0.76351 (19)	0.0229 (4)
H43	1.1560	0.4864	0.7470	0.027*
C44	0.9187 (2)	0.6113 (2)	0.84294 (18)	0.0220 (3)
H44	0.9803	0.6756	0.8784	0.026*
C45	0.7210 (2)	0.6273 (2)	0.86809 (18)	0.0219 (3)
H45	0.6473	0.7030	0.9206	0.026*
C46	0.6342 (2)	0.52893 (19)	0.81397 (16)	0.0177 (3)
H46	0.5015	0.5365	0.8299	0.021*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0091 (6)	0.0145 (7)	0.0155 (7)	0.0010 (5)	−0.0050 (5)	−0.0071 (5)
S1	0.0181 (2)	0.0174 (2)	0.0156 (2)	−0.00557 (14)	−0.00900 (15)	−0.00283 (15)
C2	0.0170 (7)	0.0195 (8)	0.0162 (7)	−0.0027 (6)	−0.0067 (5)	−0.0029 (6)
N2	0.0131 (6)	0.0136 (6)	0.0166 (6)	−0.0027 (4)	−0.0067 (5)	−0.0046 (5)
S2	0.0159 (2)	0.0162 (2)	0.0195 (2)	−0.00468 (14)	−0.00815 (15)	−0.00725 (15)
N3	0.0127 (6)	0.0137 (6)	0.0200 (6)	−0.0032 (4)	−0.0065 (5)	−0.0065 (5)
C4	0.0146 (7)	0.0122 (7)	0.0135 (6)	−0.0019 (5)	−0.0060 (5)	−0.0020 (5)
N5	0.0130 (6)	0.0253 (7)	0.0298 (7)	0.0014 (5)	−0.0091 (5)	−0.0181 (6)
C11	0.0237 (8)	0.0178 (8)	0.0230 (8)	−0.0058 (6)	−0.0106 (6)	0.0021 (6)
C41	0.0139 (7)	0.0108 (7)	0.0138 (6)	−0.0030 (5)	−0.0059 (5)	−0.0010 (5)
N42	0.0140 (6)	0.0181 (6)	0.0277 (7)	−0.0016 (5)	−0.0070 (5)	−0.0094 (5)
C43	0.0152 (7)	0.0233 (8)	0.0354 (9)	−0.0039 (6)	−0.0101 (6)	−0.0116 (7)
C44	0.0227 (8)	0.0208 (8)	0.0286 (8)	−0.0064 (6)	−0.0114 (6)	−0.0100 (6)
C45	0.0222 (8)	0.0211 (8)	0.0268 (8)	−0.0008 (6)	−0.0081 (6)	−0.0136 (6)
C46	0.0147 (7)	0.0203 (8)	0.0207 (7)	−0.0011 (6)	−0.0060 (5)	−0.0088 (6)

Geometric parameters (Å, º) top

C1—N2	1.331 (2)	C11—H11A	0.9600
C1—S2	1.6767 (14)	C11—H11B	0.9600
C1—S1	1.7663 (14)	C11—H11C	0.9600
S1—C11	1.7947 (16)	C41—N42	1.3373 (19)
C2—N2	1.4626 (19)	C41—C46	1.388 (2)
C2—H2A	0.9600	N42—C43	1.338 (2)
C2—H2B	0.9600	C43—C44	1.388 (2)
C2—H2C	0.9600	C43—H43	0.9300
N2—N3	1.4273 (17)	C44—C45	1.383 (2)
N3—C4	1.3073 (19)	C44—H44	0.9300
C4—N5	1.3292 (19)	C45—C46	1.387 (2)
C4—C41	1.4991 (19)	C45—H45	0.9300
N5—H5A	0.86 (2)	C46—H46	0.9300
N5—H5B	0.80 (2)

N2—C1—S2	124.23 (11)	S1—C11—H11B	109.5
N2—C1—S1	112.10 (10)	H11A—C11—H11B	109.5
S2—C1—S1	123.67 (9)	S1—C11—H11C	109.5
C1—S1—C11	102.69 (7)	H11A—C11—H11C	109.5
N2—C2—H2A	109.5	H11B—C11—H11C	109.5
N2—C2—H2B	109.5	N42—C41—C46	123.67 (13)
H2A—C2—H2B	109.5	N42—C41—C4	115.47 (12)
N2—C2—H2C	109.5	C46—C41—C4	120.85 (13)
H2A—C2—H2C	109.5	C41—N42—C43	117.22 (13)
H2B—C2—H2C	109.5	N42—C43—C44	123.42 (15)
C1—N2—N3	118.75 (12)	N42—C43—H43	118.3
C1—N2—C2	123.12 (12)	C44—C43—H43	118.3
N3—N2—C2	115.15 (12)	C45—C44—C43	118.43 (14)
C4—N3—N2	112.75 (11)	C45—C44—H44	120.8
N3—C4—N5	127.57 (14)	C43—C44—H44	120.8
N3—C4—C41	115.85 (12)	C44—C45—C46	119.14 (14)
N5—C4—C41	116.57 (13)	C44—C45—H45	120.4
C4—N5—H5A	122.6 (14)	C46—C45—H45	120.4
C4—N5—H5B	118.5 (15)	C45—C46—C41	118.12 (14)
H5A—N5—H5B	118 (2)	C45—C46—H46	120.9
S1—C11—H11A	109.5	C41—C46—H46	120.9

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5B···S2ⁱ	0.80 (2)	2.88 (2)	3.5431 (14)	141.3 (19)
N5—H5A···S2ⁱⁱ	0.86 (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 P1–P4 and S1-S3 against Gram-positive bacteria [MIC (MBC) (µg ml^-1) values] top

Compound	S. aureus ATCC 25923	S. aureus ATCC 6538	S. aureus ATCC 43300	S. epidermidis ATCC 12228	M. luteus ATCC 10240	B. subtilis ATCC 6633	B. cereus ATCC 10876	S. pyogenes ATCC 19615	S. pneumoniae ATCC 49619	S. mutans ATCC 25175
P1	>1000	>1000		>1000	1000	>1000				>1000
P2	1000 (>1000)	500 (>1000)	500 (>1000)	>1000 (>1000)	>1000 (>1000)	1000 (>1000)	>1000 (>1000)	250 (>1000)	>1000 (>1000)	250 (>1000)
P3	0.49 (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)
P4	0.98 (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)
S1	1.95 (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)
S2	125 (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
Vancomicin	0.98 (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)
Ciprofloxacin	0.49 (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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Planarity of hetero­aryl­dithio­carbazic acid derivatives showing tuberculostatic activity: structure–activity relationships

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Planarity of heteroaryldithiocarbazic acid derivatives showing tuberculostatic activity: structure–activity relationships