Planarity of benzoyl­thio­carbazate tuberculostatics. IV. Polymorphs of N′-(1,3-di­thio­lan-2-yl­idene)-4-nitro­benzohydrazide

The search for new tuberculostatics is important considering the occurrence of drug-resistant strains of Mycobacterium tuberculosis. Three polymorphs of N′-(1,3-di­thio­lan-2-yl­idene)-4-nitro­benzohydrazide (a potentially tuberculostatic agent), C₁₀H₉N₃O₃S₂, denoted (I1), (I2) and (I3), and the monohydrate of this compound, C₁₀H₉N₃O₃S₂·H₂O, (I4), have been characterized by single-crystal X-ray diffraction. The conformations of the mol­ecules in all these structures are very similar. Structures (I1), (I2) and (I3) provide an example of packing polymorphism resulting from different inter­molecular inter­actions.

Computing details

Data collection: APEX2 (Bruker, 2002) for I2, I3, I4. Cell refinement: SAINT-Plus (Bruker, 2003) for I2, I3, I4. Data reduction: SAINT-Plus (Bruker, 2003) for I2, I3, I4. Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for I2, I3, I4. Program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015) for I1; SHELXL97 (Sheldrick, 2008) for I2, I3, I4. Molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006) for I2, I3, I4. Software used to prepare material for publication: PLATON (Spek, 2009) for I2, I3, I4.

(I1)

Crystal data

C10H9N3O3S2	F(000) = 584
Mr = 283.32	Dx = 1.670 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 15.0609 (2) Å	Cell parameters from 9917 reflections
b = 5.0408 (1) Å	θ = 3.2–70.6°
c = 16.0954 (2) Å	µ = 4.36 mm^−1
β = 112.72°	T = 100 K
V = 1127.14 (3) Å^3	Needle, colourless
Z = 4	0.56 × 0.05 × 0.04 mm

Data collection

Bruker SMART APEXII CCD diffractometer	2105 reflections with I > 2σ(I)
ω scan	Rint = 0.023
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	θmax = 70.6°, θmin = 3.2°
Tmin = 0.749, Tmax = 1.000	h = −18→17
12799 measured reflections	k = −6→6
2142 independent reflections	l = −19→19

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.023	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.061	w = 1/[σ^2(Fo^2) + (0.0324P)^2 + 0.8787P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
2142 reflections	Δρmax = 0.36 e Å^−3
166 parameters	Δρmin = −0.25 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.23701 (9)	0.9478 (3)	0.45401 (8)	0.0108 (3)
C4	0.46277 (9)	0.7061 (3)	0.58175 (8)	0.0104 (3)
C11	0.09051 (9)	1.2146 (3)	0.46177 (9)	0.0144 (3)
H11A	0.070839	1.093472	0.498313	0.017*
H11B	0.062270	1.386985	0.462615	0.017*
C21	0.05734 (9)	1.1120 (3)	0.36573 (9)	0.0142 (3)
H21A	0.064639	1.248702	0.326415	0.017*
H21B	−0.009904	1.060827	0.343872	0.017*
C41	0.55798 (9)	0.8016 (3)	0.64870 (8)	0.0103 (3)
C42	0.63923 (9)	0.6575 (3)	0.65369 (8)	0.0123 (3)
H42	0.632583	0.512557	0.616009	0.015*
C43	0.72944 (9)	0.7302 (3)	0.71459 (9)	0.0126 (3)
H43	0.783968	0.636233	0.718265	0.015*
C44	0.73666 (9)	0.9464 (3)	0.77000 (8)	0.0114 (3)
C45	0.65751 (9)	1.0907 (3)	0.76768 (8)	0.0128 (3)
H45	0.664583	1.232831	0.806564	0.015*
C46	0.56734 (9)	1.0177 (3)	0.70581 (8)	0.0122 (3)
H46	0.513110	1.112714	0.702388	0.015*
N2	0.31362 (8)	0.8127 (2)	0.47039 (7)	0.0123 (2)
N3	0.39653 (7)	0.8970 (2)	0.54177 (7)	0.0115 (2)
H3	0.4115 (11)	1.060 (4)	0.5492 (11)	0.014*
N4	0.83275 (7)	1.0254 (2)	0.83377 (7)	0.0139 (2)
O5	0.44738 (6)	0.46871 (18)	0.56594 (6)	0.0139 (2)
O41	0.90200 (6)	0.8870 (2)	0.83924 (6)	0.0193 (2)
O42	0.83989 (7)	1.2271 (2)	0.87863 (7)	0.0224 (2)
S1	0.22099 (2)	1.23996 (6)	0.50580 (2)	0.01251 (10)
S2	0.13160 (2)	0.82734 (6)	0.36729 (2)	0.01382 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0105 (6)	0.0108 (6)	0.0115 (6)	−0.0020 (5)	0.0046 (5)	0.0000 (5)
C4	0.0096 (6)	0.0126 (6)	0.0109 (6)	0.0000 (5)	0.0059 (5)	0.0008 (5)
C11	0.0078 (6)	0.0173 (6)	0.0181 (7)	0.0016 (5)	0.0050 (5)	0.0012 (5)
C21	0.0092 (6)	0.0142 (6)	0.0173 (6)	0.0015 (5)	0.0029 (5)	0.0018 (5)
C41	0.0101 (6)	0.0110 (6)	0.0101 (6)	−0.0009 (5)	0.0044 (5)	0.0024 (5)
C42	0.0132 (6)	0.0117 (6)	0.0124 (6)	0.0001 (5)	0.0056 (5)	−0.0010 (5)
C43	0.0102 (6)	0.0140 (6)	0.0147 (6)	0.0023 (5)	0.0060 (5)	0.0015 (5)
C44	0.0096 (6)	0.0140 (6)	0.0097 (6)	−0.0022 (5)	0.0026 (5)	0.0019 (5)
C45	0.0153 (6)	0.0118 (6)	0.0119 (6)	−0.0005 (5)	0.0058 (5)	−0.0014 (5)
C46	0.0111 (6)	0.0125 (6)	0.0141 (6)	0.0021 (5)	0.0061 (5)	0.0013 (5)
N2	0.0090 (5)	0.0119 (5)	0.0139 (5)	−0.0012 (4)	0.0021 (4)	−0.0011 (4)
N3	0.0086 (5)	0.0094 (5)	0.0143 (5)	−0.0014 (4)	0.0019 (4)	−0.0015 (4)
N4	0.0115 (5)	0.0170 (6)	0.0123 (5)	−0.0017 (5)	0.0036 (4)	0.0009 (4)
O5	0.0119 (4)	0.0101 (4)	0.0177 (4)	−0.0006 (4)	0.0035 (4)	−0.0002 (4)
O41	0.0098 (4)	0.0234 (5)	0.0216 (5)	0.0021 (4)	0.0026 (4)	−0.0008 (4)
O42	0.0173 (5)	0.0229 (5)	0.0233 (5)	−0.0047 (4)	0.0038 (4)	−0.0106 (4)
S1	0.00895 (16)	0.01277 (17)	0.01515 (17)	0.00000 (11)	0.00393 (12)	−0.00342 (11)
S2	0.00943 (16)	0.01248 (17)	0.01553 (17)	−0.00012 (11)	0.00038 (12)	−0.00253 (11)

Geometric parameters (Å, º)

C1—N2	1.2766 (17)	C41—C42	1.3984 (18)
C1—S1	1.7542 (13)	C42—C43	1.3829 (18)
C1—S2	1.7680 (12)	C42—H42	0.9300
C4—O5	1.2269 (16)	C43—C44	1.3855 (19)
C4—N3	1.3562 (17)	C43—H43	0.9300
C4—C41	1.5018 (17)	C44—C45	1.3846 (18)
C11—C21	1.5198 (18)	C44—N4	1.4694 (16)
C11—S1	1.8179 (13)	C45—C46	1.3881 (18)
C11—H11A	0.9700	C45—H45	0.9300
C11—H11B	0.9700	C46—H46	0.9300
C21—S2	1.8136 (13)	N2—N3	1.3970 (15)
C21—H21A	0.9700	N3—H3	0.850 (18)
C21—H21B	0.9700	N4—O42	1.2277 (15)
C41—C46	1.3968 (18)	N4—O41	1.2292 (15)
N2—C1—S1	128.98 (10)	C41—C42—H42	120.0
N2—C1—S2	116.37 (10)	C42—C43—C44	118.43 (12)
S1—C1—S2	114.65 (7)	C42—C43—H43	120.8
O5—C4—N3	123.24 (12)	C44—C43—H43	120.8
O5—C4—C41	120.86 (11)	C45—C44—C43	122.89 (12)
N3—C4—C41	115.89 (11)	C45—C44—N4	118.81 (11)
C21—C11—S1	107.56 (9)	C43—C44—N4	118.30 (11)
C21—C11—H11A	110.2	C44—C45—C46	118.27 (12)
S1—C11—H11A	110.2	C44—C45—H45	120.9
C21—C11—H11B	110.2	C46—C45—H45	120.9
S1—C11—H11B	110.2	C45—C46—C41	120.07 (12)
H11A—C11—H11B	108.5	C45—C46—H46	120.0
C11—C21—S2	107.24 (9)	C41—C46—H46	120.0
C11—C21—H21A	110.3	C1—N2—N3	117.19 (11)
S2—C21—H21A	110.3	C4—N3—N2	115.76 (11)
C11—C21—H21B	110.3	C4—N3—H3	120.9 (11)
S2—C21—H21B	110.3	N2—N3—H3	121.0 (11)
H21A—C21—H21B	108.5	O42—N4—O41	123.28 (11)
C46—C41—C42	120.23 (11)	O42—N4—C44	118.31 (11)
C46—C41—C4	123.22 (11)	O41—N4—C44	118.41 (11)
C42—C41—C4	116.52 (11)	C1—S1—C11	94.70 (6)
C43—C42—C41	120.09 (12)	C1—S2—C21	95.75 (6)
C43—C42—H42	120.0

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O5^i	0.850 (18)	2.118 (18)	2.9687 (15)	179.2 (18)

Symmetry code: (i) x, y+1, z.

(I2)

Crystal data

C10H9N3O3S2	Z = 2
Mr = 283.32	F(000) = 292
Triclinic, P1	Dx = 1.662 Mg m^−3
a = 5.0506 (2) Å	Cu Kα radiation, λ = 1.54178 Å
b = 8.0441 (3) Å	Cell parameters from 6181 reflections
c = 14.1954 (5) Å	θ = 5.6–70.6°
α = 96.877 (1)°	µ = 4.34 mm^−1
β = 95.134 (2)°	T = 100 K
γ = 96.306 (1)°	Plate, colourless
V = 566.02 (4) Å^3	0.93 × 0.08 × 0.03 mm

Data collection

Bruker SMART APEXII CCD diffractometer	2013 reflections with I > 2σ(I)
ω scan	Rint = 0.026
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	θmax = 70.6°, θmin = 3.2°
Tmin = 0.570, Tmax = 0.753	h = −6→6
6795 measured reflections	k = −9→9
2044 independent reflections	l = −17→16

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.026	w = 1/[σ^2(Fo^2) + (0.0378P)^2 + 0.3785P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.072	(Δ/σ)max = 0.001
S = 1.09	Δρmax = 0.35 e Å^−3
2044 reflections	Δρmin = −0.34 e Å^−3
167 parameters	Extinction correction: SHELXL-2016/6 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0109 (9)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.9519 (3)	0.83114 (17)	0.23898 (10)	0.0104 (3)
C4	1.2380 (3)	0.79658 (17)	0.46338 (10)	0.0110 (3)
C11	0.6246 (3)	0.67488 (18)	0.09203 (10)	0.0141 (3)
H11A	0.724453	0.584755	0.068911	0.017*
H11B	0.439253	0.646726	0.065250	0.017*
C21	0.7408 (3)	0.84032 (18)	0.06236 (10)	0.0128 (3)
H21A	0.619648	0.924802	0.072605	0.015*
H21B	0.768383	0.825242	−0.004732	0.015*
C41	1.1675 (3)	0.76173 (17)	0.56009 (10)	0.0105 (3)
C42	1.3559 (3)	0.82985 (18)	0.63692 (10)	0.0122 (3)
H42	1.510037	0.896660	0.626419	0.015*
C43	1.3146 (3)	0.79855 (18)	0.72838 (10)	0.0127 (3)
H43	1.438497	0.844206	0.779928	0.015*
C44	1.0841 (3)	0.69744 (17)	0.74134 (10)	0.0111 (3)
C45	0.8932 (3)	0.62754 (17)	0.66716 (10)	0.0121 (3)
H45	0.741234	0.559278	0.678181	0.015*
C46	0.9349 (3)	0.66220 (17)	0.57555 (10)	0.0115 (3)
H46	0.807768	0.619030	0.524546	0.014*
N2	1.1079 (2)	0.87801 (15)	0.31583 (8)	0.0119 (3)
N3	1.0335 (2)	0.81433 (15)	0.39825 (8)	0.0111 (3)
H3	0.881 (4)	0.815 (2)	0.4118 (13)	0.013*
N4	1.0417 (3)	0.66466 (15)	0.83894 (9)	0.0138 (3)
O5	1.4725 (2)	0.80828 (14)	0.44588 (7)	0.0160 (2)
O41	1.2166 (2)	0.72301 (13)	0.90382 (7)	0.0177 (2)
O42	0.8325 (2)	0.58172 (15)	0.85171 (8)	0.0234 (3)
S1	0.64609 (7)	0.69932 (4)	0.22165 (2)	0.01259 (13)
S2	1.05729 (7)	0.90621 (4)	0.13483 (2)	0.01304 (13)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0115 (7)	0.0106 (6)	0.0100 (6)	0.0036 (5)	0.0023 (5)	0.0015 (5)
C4	0.0125 (7)	0.0098 (6)	0.0101 (7)	0.0019 (5)	0.0002 (5)	−0.0004 (5)
C11	0.0188 (7)	0.0145 (7)	0.0078 (6)	0.0019 (6)	−0.0026 (6)	0.0002 (5)
C21	0.0138 (7)	0.0158 (7)	0.0086 (6)	0.0031 (6)	−0.0009 (6)	0.0015 (5)
C41	0.0126 (7)	0.0101 (6)	0.0097 (6)	0.0055 (5)	0.0011 (5)	0.0015 (5)
C42	0.0117 (7)	0.0120 (7)	0.0129 (7)	0.0014 (5)	0.0008 (6)	0.0016 (5)
C43	0.0142 (7)	0.0125 (7)	0.0104 (7)	0.0023 (5)	−0.0020 (6)	−0.0006 (5)
C44	0.0165 (7)	0.0101 (6)	0.0081 (6)	0.0052 (5)	0.0025 (6)	0.0019 (5)
C45	0.0127 (7)	0.0110 (7)	0.0130 (7)	0.0020 (5)	0.0023 (6)	0.0022 (5)
C46	0.0125 (7)	0.0116 (6)	0.0100 (7)	0.0030 (5)	−0.0012 (5)	−0.0003 (5)
N2	0.0123 (6)	0.0152 (6)	0.0087 (6)	0.0018 (5)	0.0010 (5)	0.0030 (4)
N3	0.0098 (6)	0.0160 (6)	0.0081 (6)	0.0018 (5)	0.0019 (5)	0.0027 (4)
N4	0.0195 (6)	0.0118 (6)	0.0107 (6)	0.0035 (5)	0.0018 (5)	0.0018 (5)
O5	0.0114 (5)	0.0259 (6)	0.0122 (5)	0.0050 (4)	0.0020 (4)	0.0050 (4)
O41	0.0232 (6)	0.0196 (5)	0.0092 (5)	0.0024 (4)	−0.0031 (4)	0.0017 (4)
O42	0.0257 (6)	0.0284 (6)	0.0147 (5)	−0.0085 (5)	0.0055 (5)	0.0048 (4)
S1	0.0136 (2)	0.0149 (2)	0.00805 (19)	−0.00273 (14)	−0.00096 (14)	0.00199 (13)
S2	0.0120 (2)	0.0187 (2)	0.00858 (19)	0.00005 (14)	0.00076 (14)	0.00433 (13)

Geometric parameters (Å, º)

C1—N2	1.2788 (19)	C41—C42	1.397 (2)
C1—S1	1.7552 (14)	C42—C43	1.381 (2)
C1—S2	1.7657 (14)	C42—H42	0.9300
C4—O5	1.2279 (18)	C43—C44	1.385 (2)
C4—N3	1.3546 (18)	C43—H43	0.9300
C4—C41	1.4991 (19)	C44—C45	1.383 (2)
C11—C21	1.517 (2)	C44—N4	1.4706 (18)
C11—S1	1.8190 (14)	C45—C46	1.391 (2)
C11—H11A	0.9700	C45—H45	0.9300
C11—H11B	0.9700	C46—H46	0.9300
C21—S2	1.8121 (14)	N2—N3	1.3975 (17)
C21—H21A	0.9700	N3—H3	0.81 (2)
C21—H21B	0.9700	N4—O42	1.2259 (17)
C41—C46	1.397 (2)	N4—O41	1.2283 (16)
N2—C1—S1	128.98 (11)	C41—C42—H42	119.8
N2—C1—S2	116.29 (11)	C42—C43—C44	118.29 (13)
S1—C1—S2	114.73 (8)	C42—C43—H43	120.9
O5—C4—N3	122.70 (13)	C44—C43—H43	120.9
O5—C4—C41	120.21 (12)	C45—C44—C43	123.04 (13)
N3—C4—C41	117.10 (12)	C45—C44—N4	119.01 (13)
C21—C11—S1	108.04 (9)	C43—C44—N4	117.95 (12)
C21—C11—H11A	110.1	C44—C45—C46	118.14 (13)
S1—C11—H11A	110.1	C44—C45—H45	120.9
C21—C11—H11B	110.1	C46—C45—H45	120.9
S1—C11—H11B	110.1	C45—C46—C41	120.09 (13)
H11A—C11—H11B	108.4	C45—C46—H46	120.0
C11—C21—S2	107.18 (9)	C41—C46—H46	120.0
C11—C21—H21A	110.3	C1—N2—N3	117.14 (12)
S2—C21—H21A	110.3	C4—N3—N2	115.61 (12)
C11—C21—H21B	110.3	C4—N3—H3	122.1 (13)
S2—C21—H21B	110.3	N2—N3—H3	120.0 (13)
H21A—C21—H21B	108.5	O42—N4—O41	123.18 (12)
C46—C41—C42	120.04 (13)	O42—N4—C44	118.42 (12)
C46—C41—C4	123.86 (12)	O41—N4—C44	118.40 (12)
C42—C41—C4	116.06 (13)	C1—S1—C11	95.16 (7)
C43—C42—C41	120.38 (14)	C1—S2—C21	95.48 (7)
C43—C42—H42	119.8

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O5^i	0.81 (2)	2.16 (2)	2.9676 (16)	178.2 (18)

Symmetry code: (i) x−1, y, z.

(I3)

Crystal data

C10H9N3O3S2	F(000) = 584
Mr = 283.32	Dx = 1.617 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 7.8582 (6) Å	Cell parameters from 9309 reflections
b = 6.1279 (4) Å	θ = 5.7–72.4°
c = 24.4164 (17) Å	µ = 4.22 mm^−1
β = 98.211 (2)°	T = 100 K
V = 1163.70 (14) Å^3	Plate, colourless
Z = 4	0.38 × 0.37 × 0.08 mm

Data collection

Bruker SMART APEXII CCD diffractometer	2293 reflections with I > 2σ(I)
ω scan	Rint = 0.042
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	θmax = 72.4°, θmin = 3.7°
Tmin = 0.293, Tmax = 0.662	h = −9→9
2300 measured reflections	k = 0→7
2300 independent reflections	l = 0→30

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.099	w = 1/[σ^2(Fo^2) + (0.0629P)^2 + 0.6885P] where P = (Fo^2 + 2Fc^2)/3
S = 1.14	(Δ/σ)max = 0.001
2300 reflections	Δρmax = 0.44 e Å^−3
167 parameters	Δρmin = −0.60 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.27403 (19)	0.8154 (2)	0.29175 (6)	0.0114 (3)
C4	0.02621 (19)	0.7084 (2)	0.17039 (6)	0.0118 (3)
C11	0.5133 (2)	1.1018 (3)	0.33254 (6)	0.0159 (3)
H11A	0.609234	1.185490	0.322728	0.019*
H11B	0.466033	1.178855	0.361640	0.019*
C21	0.5734 (2)	0.8762 (3)	0.35244 (6)	0.0158 (3)
H21A	0.637750	0.885177	0.389360	0.019*
H21B	0.647693	0.814785	0.327921	0.019*
C41	−0.05310 (19)	0.8397 (3)	0.12140 (6)	0.0116 (3)
C42	−0.1740 (2)	0.7365 (3)	0.08220 (7)	0.0140 (3)
H42	−0.207739	0.593879	0.088059	0.017*
C43	−0.2436 (2)	0.8467 (3)	0.03462 (6)	0.0159 (3)
H43	−0.325709	0.780995	0.008592	0.019*
C44	−0.1877 (2)	1.0573 (3)	0.02693 (6)	0.0153 (3)
C45	−0.0662 (2)	1.1628 (3)	0.06433 (6)	0.0148 (3)
H45	−0.029988	1.303490	0.057564	0.018*
C46	0.00035 (19)	1.0516 (2)	0.11251 (6)	0.0130 (3)
H46	0.080608	1.119300	0.138757	0.016*
N2	0.14883 (17)	0.7093 (2)	0.26448 (5)	0.0126 (3)
N3	0.07176 (17)	0.8271 (2)	0.21740 (5)	0.0121 (3)
H3	0.016 (3)	0.937 (4)	0.2235 (8)	0.015*
N4	−0.26201 (19)	1.1754 (3)	−0.02341 (6)	0.0204 (3)
O5	0.05660 (14)	0.51366 (18)	0.16611 (5)	0.0159 (3)
O41	−0.35840 (18)	1.0753 (2)	−0.05869 (5)	0.0294 (3)
O42	−0.2243 (2)	1.3682 (2)	−0.02764 (6)	0.0372 (4)
S1	0.34971 (5)	1.06971 (6)	0.27249 (2)	0.01503 (15)
S2	0.38495 (5)	0.70489 (6)	0.35298 (2)	0.01385 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0143 (7)	0.0106 (7)	0.0097 (7)	0.0021 (5)	0.0033 (5)	0.0013 (5)
C4	0.0098 (6)	0.0124 (8)	0.0131 (7)	−0.0009 (5)	0.0014 (5)	0.0001 (5)
C11	0.0147 (7)	0.0170 (8)	0.0150 (8)	−0.0036 (6)	−0.0005 (6)	−0.0009 (6)
C21	0.0136 (7)	0.0187 (8)	0.0142 (7)	−0.0007 (6)	−0.0010 (5)	−0.0009 (6)
C41	0.0116 (7)	0.0118 (7)	0.0114 (7)	0.0022 (6)	0.0016 (5)	−0.0023 (6)
C42	0.0139 (7)	0.0132 (7)	0.0145 (8)	−0.0003 (6)	0.0010 (6)	−0.0033 (6)
C43	0.0139 (7)	0.0200 (8)	0.0133 (7)	0.0014 (6)	−0.0003 (6)	−0.0054 (6)
C44	0.0182 (8)	0.0184 (8)	0.0095 (7)	0.0065 (6)	0.0027 (6)	0.0002 (6)
C45	0.0183 (7)	0.0129 (7)	0.0137 (7)	0.0024 (6)	0.0039 (6)	−0.0008 (6)
C46	0.0127 (7)	0.0136 (7)	0.0125 (7)	0.0008 (5)	0.0007 (5)	−0.0026 (5)
N2	0.0150 (6)	0.0109 (6)	0.0112 (6)	0.0013 (5)	−0.0009 (5)	0.0016 (4)
N3	0.0141 (6)	0.0092 (6)	0.0117 (6)	0.0027 (5)	−0.0025 (5)	0.0003 (5)
N4	0.0245 (7)	0.0242 (8)	0.0118 (7)	0.0085 (6)	0.0006 (6)	0.0001 (5)
O5	0.0188 (5)	0.0100 (5)	0.0183 (5)	0.0016 (4)	0.0012 (4)	−0.0016 (4)
O41	0.0295 (7)	0.0378 (8)	0.0174 (6)	0.0012 (6)	−0.0091 (5)	0.0013 (5)
O42	0.0618 (10)	0.0229 (7)	0.0226 (7)	0.0040 (7)	−0.0088 (6)	0.0070 (5)
S1	0.0165 (2)	0.0136 (2)	0.0141 (2)	−0.00375 (13)	−0.00081 (15)	0.00427 (12)
S2	0.0150 (2)	0.0144 (2)	0.0112 (2)	−0.00060 (13)	−0.00138 (15)	0.00337 (12)

Geometric parameters (Å, º)

C1—N2	1.283 (2)	C41—C42	1.400 (2)
C1—S2	1.7553 (15)	C42—C43	1.387 (2)
C1—S1	1.7560 (15)	C42—H42	0.9300
C4—O5	1.2247 (19)	C43—C44	1.385 (2)
C4—N3	1.363 (2)	C43—H43	0.9300
C4—C41	1.501 (2)	C44—C45	1.384 (2)
C11—C21	1.518 (2)	C44—N4	1.473 (2)
C11—S1	1.8172 (16)	C45—C46	1.395 (2)
C11—H11A	0.9700	C45—H45	0.9300
C11—H11B	0.9700	C46—H46	0.9300
C21—S2	1.8170 (16)	N2—N3	1.4179 (17)
C21—H21A	0.9700	N3—H3	0.83 (2)
C21—H21B	0.9700	N4—O42	1.226 (2)
C41—C46	1.392 (2)	N4—O41	1.227 (2)
N2—C1—S2	119.82 (12)	C41—C42—H42	120.0
N2—C1—S1	125.06 (12)	C44—C43—C42	118.20 (14)
S2—C1—S1	115.12 (9)	C44—C43—H43	120.9
O5—C4—N3	124.13 (14)	C42—C43—H43	120.9
O5—C4—C41	121.19 (14)	C45—C44—C43	123.26 (15)
N3—C4—C41	114.50 (13)	C45—C44—N4	118.37 (14)
C21—C11—S1	108.17 (11)	C43—C44—N4	118.36 (14)
C21—C11—H11A	110.1	C44—C45—C46	117.95 (14)
S1—C11—H11A	110.1	C44—C45—H45	121.0
C21—C11—H11B	110.1	C46—C45—H45	121.0
S1—C11—H11B	110.1	C41—C46—C45	120.15 (14)
H11A—C11—H11B	108.4	C41—C46—H46	119.9
C11—C21—S2	108.16 (10)	C45—C46—H46	119.9
C11—C21—H21A	110.1	C1—N2—N3	111.72 (12)
S2—C21—H21A	110.1	C4—N3—N2	116.21 (12)
C11—C21—H21B	110.1	C4—N3—H3	120.3 (14)
S2—C21—H21B	110.1	N2—N3—H3	116.3 (14)
H21A—C21—H21B	108.4	O42—N4—O41	123.72 (14)
C46—C41—C42	120.37 (14)	O42—N4—C44	118.15 (14)
C46—C41—C4	121.60 (13)	O41—N4—C44	118.13 (14)
C42—C41—C4	117.84 (14)	C1—S1—C11	96.17 (7)
C43—C42—C41	120.05 (15)	C1—S2—C21	94.42 (7)
C43—C42—H42	120.0

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N2^i	0.83 (2)	2.16 (2)	2.9843 (19)	175 (2)

Symmetry code: (i) −x, y+1/2, −z+1/2.

(I4)

Crystal data

C10H9N3O3S2·H2O	F(000) = 624
Mr = 301.34	Dx = 1.626 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
a = 7.3654 (3) Å	Cell parameters from 9981 reflections
b = 6.4550 (2) Å	θ = 3.4–72.5°
c = 25.8911 (9) Å	µ = 4.09 mm^−1
β = 90.808 (1)°	T = 100 K
V = 1230.84 (8) Å^3	Plate, colourless
Z = 4	0.60 × 0.46 × 0.03 mm

Data collection

Bruker SMART APEXII CCD diffractometer	2406 reflections with I > 2σ(I)
ω scan	Rint = 0.029
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	θmax = 72.5°, θmin = 3.4°
Tmin = 0.507, Tmax = 0.754	h = −9→9
13701 measured reflections	k = −7→6
2423 independent reflections	l = −31→32

Refinement

Refinement on F^2	3 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.069	w = 1/[σ^2(Fo^2) + (0.032P)^2 + 0.9597P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.002
2423 reflections	Δρmax = 0.53 e Å^−3
181 parameters	Δρmin = −0.26 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.49542 (16)	0.7865 (2)	0.72028 (5)	0.0116 (2)
N2	0.47914 (15)	0.72085 (17)	0.67374 (4)	0.0141 (2)
N3	0.56255 (15)	0.84599 (18)	0.63652 (4)	0.0129 (2)
H3	0.546 (2)	0.977 (3)	0.6387 (7)	0.015*
C4	0.60402 (17)	0.7527 (2)	0.59136 (5)	0.0127 (3)
O5	0.58811 (15)	0.56561 (15)	0.58418 (4)	0.0215 (2)
C41	0.67658 (16)	0.8897 (2)	0.54942 (5)	0.0111 (2)
C42	0.68418 (17)	0.8029 (2)	0.50001 (5)	0.0127 (3)
H42	0.644557	0.667756	0.494600	0.015*
C43	0.75040 (17)	0.9172 (2)	0.45911 (5)	0.0132 (3)
H43	0.755957	0.860402	0.426153	0.016*
C44	0.80809 (16)	1.1178 (2)	0.46848 (5)	0.0118 (3)
C45	0.80235 (17)	1.2094 (2)	0.51684 (5)	0.0130 (3)
H45	0.841577	1.344905	0.521914	0.016*
C46	0.73622 (17)	1.0925 (2)	0.55751 (5)	0.0127 (3)
H46	0.731640	1.149894	0.590416	0.015*
N4	0.88001 (15)	1.23893 (18)	0.42488 (4)	0.0149 (2)
O41	0.90489 (15)	1.14833 (16)	0.38404 (4)	0.0242 (2)
O42	0.91342 (15)	1.42324 (16)	0.43183 (4)	0.0242 (2)
S1	0.62612 (4)	0.99731 (5)	0.74193 (2)	0.01691 (10)
S2	0.38078 (4)	0.65196 (5)	0.76904 (2)	0.01598 (10)
C11	0.5457 (2)	0.9915 (2)	0.80762 (6)	0.0244 (3)
H11A	0.637506	1.047898	0.830887	0.029*
H11B	0.436793	1.075001	0.810446	0.029*
C21	0.5053 (2)	0.7706 (3)	0.82192 (5)	0.0234 (3)
H21A	0.433759	0.766511	0.853070	0.028*
H21B	0.617641	0.695948	0.828371	0.028*
O1W	0.45304 (15)	0.26144 (15)	0.64596 (4)	0.0213 (2)
H2W	0.444 (3)	0.298 (3)	0.6759 (4)	0.032*
H1W	0.487 (3)	0.366 (2)	0.6314 (6)	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0120 (6)	0.0117 (6)	0.0111 (6)	0.0001 (5)	0.0018 (5)	0.0009 (5)
N2	0.0192 (6)	0.0120 (5)	0.0110 (5)	−0.0019 (4)	0.0035 (4)	0.0012 (4)
N3	0.0200 (6)	0.0086 (5)	0.0102 (5)	−0.0014 (4)	0.0031 (4)	0.0010 (4)
C4	0.0142 (6)	0.0126 (6)	0.0115 (6)	0.0011 (5)	0.0013 (5)	0.0006 (5)
O5	0.0384 (6)	0.0109 (5)	0.0155 (5)	−0.0013 (4)	0.0108 (4)	−0.0007 (4)
C41	0.0105 (5)	0.0120 (6)	0.0109 (6)	0.0019 (5)	0.0007 (4)	0.0012 (5)
C42	0.0144 (6)	0.0106 (6)	0.0130 (6)	0.0006 (5)	0.0008 (5)	−0.0008 (5)
C43	0.0150 (6)	0.0138 (6)	0.0107 (6)	0.0018 (5)	0.0011 (5)	−0.0016 (5)
C44	0.0103 (6)	0.0138 (6)	0.0114 (6)	0.0009 (5)	0.0015 (4)	0.0034 (5)
C45	0.0129 (6)	0.0116 (6)	0.0144 (6)	−0.0009 (5)	0.0001 (5)	0.0001 (5)
C46	0.0138 (6)	0.0142 (6)	0.0101 (6)	0.0001 (5)	0.0000 (5)	−0.0016 (5)
N4	0.0154 (5)	0.0162 (6)	0.0130 (5)	−0.0005 (4)	0.0014 (4)	0.0031 (4)
O41	0.0376 (6)	0.0224 (6)	0.0127 (5)	−0.0028 (4)	0.0082 (4)	0.0008 (4)
O42	0.0352 (6)	0.0164 (5)	0.0211 (5)	−0.0079 (4)	0.0047 (4)	0.0031 (4)
S1	0.01991 (18)	0.01910 (19)	0.01174 (17)	−0.00822 (12)	0.00094 (12)	−0.00152 (12)
S2	0.01892 (18)	0.01772 (19)	0.01142 (17)	−0.00419 (12)	0.00424 (12)	0.00176 (12)
C11	0.0313 (8)	0.0307 (9)	0.0111 (7)	−0.0074 (6)	0.0022 (6)	−0.0067 (6)
C21	0.0252 (7)	0.0337 (8)	0.0112 (7)	−0.0021 (6)	0.0014 (5)	0.0007 (6)
O1W	0.0377 (6)	0.0112 (5)	0.0153 (5)	−0.0013 (4)	0.0088 (4)	0.0007 (4)

Geometric parameters (Å, º)

C1—N2	1.2814 (17)	C44—N4	1.4775 (16)
C1—S1	1.7543 (13)	C45—C46	1.3891 (18)
C1—S2	1.7582 (13)	C45—H45	0.9300
N2—N3	1.4054 (15)	C46—H46	0.9300
N3—C4	1.3540 (17)	N4—O41	1.2243 (15)
N3—H3	0.858 (18)	N4—O42	1.2277 (16)
C4—O5	1.2270 (17)	S1—C11	1.8092 (15)
C4—C41	1.5047 (17)	S2—C21	1.8075 (15)
C41—C46	1.3954 (19)	C11—C21	1.504 (2)
C41—C42	1.3984 (18)	C11—H11A	0.9700
C42—C43	1.3849 (18)	C11—H11B	0.9700
C42—H42	0.9300	C21—H21A	0.9700
C43—C44	1.3836 (19)	C21—H21B	0.9700
C43—H43	0.9300	O1W—H2W	0.814 (9)
C44—C45	1.3858 (18)	O1W—H1W	0.814 (9)
N2—C1—S1	126.92 (10)	C44—C45—H45	121.0
N2—C1—S2	118.19 (10)	C46—C45—H45	121.0
S1—C1—S2	114.87 (7)	C45—C46—C41	120.57 (12)
C1—N2—N3	114.75 (11)	C45—C46—H46	119.7
C4—N3—N2	116.26 (11)	C41—C46—H46	119.7
C4—N3—H3	122.0 (12)	O41—N4—O42	123.88 (12)
N2—N3—H3	117.3 (11)	O41—N4—C44	117.82 (11)
O5—C4—N3	123.12 (12)	O42—N4—C44	118.29 (11)
O5—C4—C41	120.23 (11)	C1—S1—C11	95.68 (7)
N3—C4—C41	116.63 (11)	C1—S2—C21	95.21 (7)
C46—C41—C42	119.78 (12)	C21—C11—S1	108.63 (10)
C46—C41—C4	123.88 (11)	C21—C11—H11A	110.0
C42—C41—C4	116.33 (11)	S1—C11—H11A	110.0
C43—C42—C41	120.34 (12)	C21—C11—H11B	110.0
C43—C42—H42	119.8	S1—C11—H11B	110.0
C41—C42—H42	119.8	H11A—C11—H11B	108.3
C44—C43—C42	118.36 (12)	C11—C21—S2	108.38 (10)
C44—C43—H43	120.8	C11—C21—H21A	110.0
C42—C43—H43	120.8	S2—C21—H21A	110.0
C43—C44—C45	122.99 (12)	C11—C21—H21B	110.0
C43—C44—N4	118.28 (11)	S2—C21—H21B	110.0
C45—C44—N4	118.72 (12)	H21A—C21—H21B	108.4
C44—C45—C46	117.96 (12)	H2W—O1W—H1W	103.4 (16)
S1—C1—N2—N3	−6.44 (17)	N4—C44—C45—C46	−179.30 (11)
S2—C1—N2—N3	175.08 (9)	C44—C45—C46—C41	−0.42 (19)
C1—N2—N3—C4	157.92 (12)	C42—C41—C46—C45	0.30 (19)
N2—N3—C4—O5	−7.15 (19)	C4—C41—C46—C45	179.70 (11)
N2—N3—C4—C41	174.25 (10)	C43—C44—N4—O41	−8.38 (17)
O5—C4—C41—C46	−165.43 (13)	C45—C44—N4—O41	171.26 (12)
N3—C4—C41—C46	13.21 (18)	C43—C44—N4—O42	172.52 (12)
O5—C4—C41—C42	13.98 (18)	C45—C44—N4—O42	−7.85 (18)
N3—C4—C41—C42	−167.38 (11)	N2—C1—S1—C11	173.37 (13)
C46—C41—C42—C43	−0.05 (19)	S2—C1—S1—C11	−8.11 (9)
C4—C41—C42—C43	−179.49 (11)	N2—C1—S2—C21	165.37 (11)
C41—C42—C43—C44	−0.06 (19)	S1—C1—S2—C21	−13.28 (9)
C42—C43—C44—C45	−0.08 (19)	C1—S1—C11—C21	32.19 (12)
C42—C43—C44—N4	179.54 (11)	S1—C11—C21—S2	−45.10 (13)
C43—C44—C45—C46	0.32 (19)	C1—S2—C21—C11	35.18 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O5	0.81 (1)	1.93 (1)	2.7291 (14)	166 (2)
O1W—H1W···N2	0.81 (1)	2.54 (2)	3.0569 (15)	123 (2)
N3—H3···O1W^i	0.858 (18)	1.968 (19)	2.8120 (15)	167.6 (16)

Symmetry code: (i) x, y+1, z.