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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617012566/fn3245sup1.cif
Contains datablocks I1, I2, I3, I4, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617012566/fn3245I1sup2.hkl
Contains datablock I1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617012566/fn3245I2sup3.hkl
Contains datablock I2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617012566/fn3245I3sup4.hkl
Contains datablock I3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617012566/fn3245I4sup5.hkl
Contains datablock I4

CCDC references: 1571916; 1571915; 1571914; 1571913

Computing details top

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) top
Crystal data top
C10H9N3O3S2F(000) = 584
Mr = 283.32Dx = 1.670 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 15.0609 (2) ÅCell parameters from 9917 reflections
b = 5.0408 (1) Åθ = 3.2–70.6°
c = 16.0954 (2) ŵ = 4.36 mm1
β = 112.72°T = 100 K
V = 1127.14 (3) Å3Needle, colourless
Z = 40.56 × 0.05 × 0.04 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
2105 reflections with I > 2σ(I)
ω scanRint = 0.023
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
θmax = 70.6°, θmin = 3.2°
Tmin = 0.749, Tmax = 1.000h = 1817
12799 measured reflectionsk = 66
2142 independent reflectionsl = 1919
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.023H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.061 w = 1/[σ2(Fo2) + (0.0324P)2 + 0.8787P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
2142 reflectionsΔρmax = 0.36 e Å3
166 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
C10.23701 (9)0.9478 (3)0.45401 (8)0.0108 (3)
C40.46277 (9)0.7061 (3)0.58175 (8)0.0104 (3)
C110.09051 (9)1.2146 (3)0.46177 (9)0.0144 (3)
H11A0.0708391.0934720.4983130.017*
H11B0.0622701.3869850.4626150.017*
C210.05734 (9)1.1120 (3)0.36573 (9)0.0142 (3)
H21A0.0646391.2487020.3264150.017*
H21B0.0099041.0608270.3438720.017*
C410.55798 (9)0.8016 (3)0.64870 (8)0.0103 (3)
C420.63923 (9)0.6575 (3)0.65369 (8)0.0123 (3)
H420.6325830.5125570.6160090.015*
C430.72944 (9)0.7302 (3)0.71459 (9)0.0126 (3)
H430.7839680.6362330.7182650.015*
C440.73666 (9)0.9464 (3)0.77000 (8)0.0114 (3)
C450.65751 (9)1.0907 (3)0.76768 (8)0.0128 (3)
H450.6645831.2328310.8065640.015*
C460.56734 (9)1.0177 (3)0.70581 (8)0.0122 (3)
H460.5131101.1127140.7023880.015*
N20.31362 (8)0.8127 (2)0.47039 (7)0.0123 (2)
N30.39653 (7)0.8970 (2)0.54177 (7)0.0115 (2)
H30.4115 (11)1.060 (4)0.5492 (11)0.014*
N40.83275 (7)1.0254 (2)0.83377 (7)0.0139 (2)
O50.44738 (6)0.46871 (18)0.56594 (6)0.0139 (2)
O410.90200 (6)0.8870 (2)0.83924 (6)0.0193 (2)
O420.83989 (7)1.2271 (2)0.87863 (7)0.0224 (2)
S10.22099 (2)1.23996 (6)0.50580 (2)0.01251 (10)
S20.13160 (2)0.82734 (6)0.36729 (2)0.01382 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0105 (6)0.0108 (6)0.0115 (6)0.0020 (5)0.0046 (5)0.0000 (5)
C40.0096 (6)0.0126 (6)0.0109 (6)0.0000 (5)0.0059 (5)0.0008 (5)
C110.0078 (6)0.0173 (6)0.0181 (7)0.0016 (5)0.0050 (5)0.0012 (5)
C210.0092 (6)0.0142 (6)0.0173 (6)0.0015 (5)0.0029 (5)0.0018 (5)
C410.0101 (6)0.0110 (6)0.0101 (6)0.0009 (5)0.0044 (5)0.0024 (5)
C420.0132 (6)0.0117 (6)0.0124 (6)0.0001 (5)0.0056 (5)0.0010 (5)
C430.0102 (6)0.0140 (6)0.0147 (6)0.0023 (5)0.0060 (5)0.0015 (5)
C440.0096 (6)0.0140 (6)0.0097 (6)0.0022 (5)0.0026 (5)0.0019 (5)
C450.0153 (6)0.0118 (6)0.0119 (6)0.0005 (5)0.0058 (5)0.0014 (5)
C460.0111 (6)0.0125 (6)0.0141 (6)0.0021 (5)0.0061 (5)0.0013 (5)
N20.0090 (5)0.0119 (5)0.0139 (5)0.0012 (4)0.0021 (4)0.0011 (4)
N30.0086 (5)0.0094 (5)0.0143 (5)0.0014 (4)0.0019 (4)0.0015 (4)
N40.0115 (5)0.0170 (6)0.0123 (5)0.0017 (5)0.0036 (4)0.0009 (4)
O50.0119 (4)0.0101 (4)0.0177 (4)0.0006 (4)0.0035 (4)0.0002 (4)
O410.0098 (4)0.0234 (5)0.0216 (5)0.0021 (4)0.0026 (4)0.0008 (4)
O420.0173 (5)0.0229 (5)0.0233 (5)0.0047 (4)0.0038 (4)0.0106 (4)
S10.00895 (16)0.01277 (17)0.01515 (17)0.00000 (11)0.00393 (12)0.00342 (11)
S20.00943 (16)0.01248 (17)0.01553 (17)0.00012 (11)0.00038 (12)0.00253 (11)
Geometric parameters (Å, º) top
C1—N21.2766 (17)C41—C421.3984 (18)
C1—S11.7542 (13)C42—C431.3829 (18)
C1—S21.7680 (12)C42—H420.9300
C4—O51.2269 (16)C43—C441.3855 (19)
C4—N31.3562 (17)C43—H430.9300
C4—C411.5018 (17)C44—C451.3846 (18)
C11—C211.5198 (18)C44—N41.4694 (16)
C11—S11.8179 (13)C45—C461.3881 (18)
C11—H11A0.9700C45—H450.9300
C11—H11B0.9700C46—H460.9300
C21—S21.8136 (13)N2—N31.3970 (15)
C21—H21A0.9700N3—H30.850 (18)
C21—H21B0.9700N4—O421.2277 (15)
C41—C461.3968 (18)N4—O411.2292 (15)
N2—C1—S1128.98 (10)C41—C42—H42120.0
N2—C1—S2116.37 (10)C42—C43—C44118.43 (12)
S1—C1—S2114.65 (7)C42—C43—H43120.8
O5—C4—N3123.24 (12)C44—C43—H43120.8
O5—C4—C41120.86 (11)C45—C44—C43122.89 (12)
N3—C4—C41115.89 (11)C45—C44—N4118.81 (11)
C21—C11—S1107.56 (9)C43—C44—N4118.30 (11)
C21—C11—H11A110.2C44—C45—C46118.27 (12)
S1—C11—H11A110.2C44—C45—H45120.9
C21—C11—H11B110.2C46—C45—H45120.9
S1—C11—H11B110.2C45—C46—C41120.07 (12)
H11A—C11—H11B108.5C45—C46—H46120.0
C11—C21—S2107.24 (9)C41—C46—H46120.0
C11—C21—H21A110.3C1—N2—N3117.19 (11)
S2—C21—H21A110.3C4—N3—N2115.76 (11)
C11—C21—H21B110.3C4—N3—H3120.9 (11)
S2—C21—H21B110.3N2—N3—H3121.0 (11)
H21A—C21—H21B108.5O42—N4—O41123.28 (11)
C46—C41—C42120.23 (11)O42—N4—C44118.31 (11)
C46—C41—C4123.22 (11)O41—N4—C44118.41 (11)
C42—C41—C4116.52 (11)C1—S1—C1194.70 (6)
C43—C42—C41120.09 (12)C1—S2—C2195.75 (6)
C43—C42—H42120.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O5i0.850 (18)2.118 (18)2.9687 (15)179.2 (18)
Symmetry code: (i) x, y+1, z.
(I2) top
Crystal data top
C10H9N3O3S2Z = 2
Mr = 283.32F(000) = 292
Triclinic, P1Dx = 1.662 Mg m3
a = 5.0506 (2) ÅCu Kα radiation, λ = 1.54178 Å
b = 8.0441 (3) ÅCell parameters from 6181 reflections
c = 14.1954 (5) Åθ = 5.6–70.6°
α = 96.877 (1)°µ = 4.34 mm1
β = 95.134 (2)°T = 100 K
γ = 96.306 (1)°Plate, colourless
V = 566.02 (4) Å30.93 × 0.08 × 0.03 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
2013 reflections with I > 2σ(I)
ω scanRint = 0.026
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
θmax = 70.6°, θmin = 3.2°
Tmin = 0.570, Tmax = 0.753h = 66
6795 measured reflectionsk = 99
2044 independent reflectionsl = 1716
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)] = 0.026 w = 1/[σ2(Fo2) + (0.0378P)2 + 0.3785P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.072(Δ/σ)max = 0.001
S = 1.09Δρmax = 0.35 e Å3
2044 reflectionsΔρmin = 0.34 e Å3
167 parametersExtinction correction: SHELXL-2016/6 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0109 (9)
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
C10.9519 (3)0.83114 (17)0.23898 (10)0.0104 (3)
C41.2380 (3)0.79658 (17)0.46338 (10)0.0110 (3)
C110.6246 (3)0.67488 (18)0.09203 (10)0.0141 (3)
H11A0.7244530.5847550.0689110.017*
H11B0.4392530.6467260.0652500.017*
C210.7408 (3)0.84032 (18)0.06236 (10)0.0128 (3)
H21A0.6196480.9248020.0726050.015*
H21B0.7683830.8252420.0047320.015*
C411.1675 (3)0.76173 (17)0.56009 (10)0.0105 (3)
C421.3559 (3)0.82985 (18)0.63692 (10)0.0122 (3)
H421.5100370.8966600.6264190.015*
C431.3146 (3)0.79855 (18)0.72838 (10)0.0127 (3)
H431.4384970.8442060.7799280.015*
C441.0841 (3)0.69744 (17)0.74134 (10)0.0111 (3)
C450.8932 (3)0.62754 (17)0.66716 (10)0.0121 (3)
H450.7412340.5592780.6781810.015*
C460.9349 (3)0.66220 (17)0.57555 (10)0.0115 (3)
H460.8077680.6190300.5245460.014*
N21.1079 (2)0.87801 (15)0.31583 (8)0.0119 (3)
N31.0335 (2)0.81433 (15)0.39825 (8)0.0111 (3)
H30.881 (4)0.815 (2)0.4118 (13)0.013*
N41.0417 (3)0.66466 (15)0.83894 (9)0.0138 (3)
O51.4725 (2)0.80828 (14)0.44588 (7)0.0160 (2)
O411.2166 (2)0.72301 (13)0.90382 (7)0.0177 (2)
O420.8325 (2)0.58172 (15)0.85171 (8)0.0234 (3)
S10.64609 (7)0.69932 (4)0.22165 (2)0.01259 (13)
S21.05729 (7)0.90621 (4)0.13483 (2)0.01304 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0115 (7)0.0106 (6)0.0100 (6)0.0036 (5)0.0023 (5)0.0015 (5)
C40.0125 (7)0.0098 (6)0.0101 (7)0.0019 (5)0.0002 (5)0.0004 (5)
C110.0188 (7)0.0145 (7)0.0078 (6)0.0019 (6)0.0026 (6)0.0002 (5)
C210.0138 (7)0.0158 (7)0.0086 (6)0.0031 (6)0.0009 (6)0.0015 (5)
C410.0126 (7)0.0101 (6)0.0097 (6)0.0055 (5)0.0011 (5)0.0015 (5)
C420.0117 (7)0.0120 (7)0.0129 (7)0.0014 (5)0.0008 (6)0.0016 (5)
C430.0142 (7)0.0125 (7)0.0104 (7)0.0023 (5)0.0020 (6)0.0006 (5)
C440.0165 (7)0.0101 (6)0.0081 (6)0.0052 (5)0.0025 (6)0.0019 (5)
C450.0127 (7)0.0110 (7)0.0130 (7)0.0020 (5)0.0023 (6)0.0022 (5)
C460.0125 (7)0.0116 (6)0.0100 (7)0.0030 (5)0.0012 (5)0.0003 (5)
N20.0123 (6)0.0152 (6)0.0087 (6)0.0018 (5)0.0010 (5)0.0030 (4)
N30.0098 (6)0.0160 (6)0.0081 (6)0.0018 (5)0.0019 (5)0.0027 (4)
N40.0195 (6)0.0118 (6)0.0107 (6)0.0035 (5)0.0018 (5)0.0018 (5)
O50.0114 (5)0.0259 (6)0.0122 (5)0.0050 (4)0.0020 (4)0.0050 (4)
O410.0232 (6)0.0196 (5)0.0092 (5)0.0024 (4)0.0031 (4)0.0017 (4)
O420.0257 (6)0.0284 (6)0.0147 (5)0.0085 (5)0.0055 (5)0.0048 (4)
S10.0136 (2)0.0149 (2)0.00805 (19)0.00273 (14)0.00096 (14)0.00199 (13)
S20.0120 (2)0.0187 (2)0.00858 (19)0.00005 (14)0.00076 (14)0.00433 (13)
Geometric parameters (Å, º) top
C1—N21.2788 (19)C41—C421.397 (2)
C1—S11.7552 (14)C42—C431.381 (2)
C1—S21.7657 (14)C42—H420.9300
C4—O51.2279 (18)C43—C441.385 (2)
C4—N31.3546 (18)C43—H430.9300
C4—C411.4991 (19)C44—C451.383 (2)
C11—C211.517 (2)C44—N41.4706 (18)
C11—S11.8190 (14)C45—C461.391 (2)
C11—H11A0.9700C45—H450.9300
C11—H11B0.9700C46—H460.9300
C21—S21.8121 (14)N2—N31.3975 (17)
C21—H21A0.9700N3—H30.81 (2)
C21—H21B0.9700N4—O421.2259 (17)
C41—C461.397 (2)N4—O411.2283 (16)
N2—C1—S1128.98 (11)C41—C42—H42119.8
N2—C1—S2116.29 (11)C42—C43—C44118.29 (13)
S1—C1—S2114.73 (8)C42—C43—H43120.9
O5—C4—N3122.70 (13)C44—C43—H43120.9
O5—C4—C41120.21 (12)C45—C44—C43123.04 (13)
N3—C4—C41117.10 (12)C45—C44—N4119.01 (13)
C21—C11—S1108.04 (9)C43—C44—N4117.95 (12)
C21—C11—H11A110.1C44—C45—C46118.14 (13)
S1—C11—H11A110.1C44—C45—H45120.9
C21—C11—H11B110.1C46—C45—H45120.9
S1—C11—H11B110.1C45—C46—C41120.09 (13)
H11A—C11—H11B108.4C45—C46—H46120.0
C11—C21—S2107.18 (9)C41—C46—H46120.0
C11—C21—H21A110.3C1—N2—N3117.14 (12)
S2—C21—H21A110.3C4—N3—N2115.61 (12)
C11—C21—H21B110.3C4—N3—H3122.1 (13)
S2—C21—H21B110.3N2—N3—H3120.0 (13)
H21A—C21—H21B108.5O42—N4—O41123.18 (12)
C46—C41—C42120.04 (13)O42—N4—C44118.42 (12)
C46—C41—C4123.86 (12)O41—N4—C44118.40 (12)
C42—C41—C4116.06 (13)C1—S1—C1195.16 (7)
C43—C42—C41120.38 (14)C1—S2—C2195.48 (7)
C43—C42—H42119.8
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O5i0.81 (2)2.16 (2)2.9676 (16)178.2 (18)
Symmetry code: (i) x1, y, z.
(I3) top
Crystal data top
C10H9N3O3S2F(000) = 584
Mr = 283.32Dx = 1.617 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 7.8582 (6) ÅCell parameters from 9309 reflections
b = 6.1279 (4) Åθ = 5.7–72.4°
c = 24.4164 (17) ŵ = 4.22 mm1
β = 98.211 (2)°T = 100 K
V = 1163.70 (14) Å3Plate, colourless
Z = 40.38 × 0.37 × 0.08 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
2293 reflections with I > 2σ(I)
ω scanRint = 0.042
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
θmax = 72.4°, θmin = 3.7°
Tmin = 0.293, Tmax = 0.662h = 99
2300 measured reflectionsk = 07
2300 independent reflectionsl = 030
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.099 w = 1/[σ2(Fo2) + (0.0629P)2 + 0.6885P]
where P = (Fo2 + 2Fc2)/3
S = 1.14(Δ/σ)max = 0.001
2300 reflectionsΔρmax = 0.44 e Å3
167 parametersΔρmin = 0.60 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
C10.27403 (19)0.8154 (2)0.29175 (6)0.0114 (3)
C40.02621 (19)0.7084 (2)0.17039 (6)0.0118 (3)
C110.5133 (2)1.1018 (3)0.33254 (6)0.0159 (3)
H11A0.6092341.1854900.3227280.019*
H11B0.4660331.1788550.3616400.019*
C210.5734 (2)0.8762 (3)0.35244 (6)0.0158 (3)
H21A0.6377500.8851770.3893600.019*
H21B0.6476930.8147850.3279210.019*
C410.05310 (19)0.8397 (3)0.12140 (6)0.0116 (3)
C420.1740 (2)0.7365 (3)0.08220 (7)0.0140 (3)
H420.2077390.5938790.0880590.017*
C430.2436 (2)0.8467 (3)0.03462 (6)0.0159 (3)
H430.3257090.7809950.0085920.019*
C440.1877 (2)1.0573 (3)0.02693 (6)0.0153 (3)
C450.0662 (2)1.1628 (3)0.06433 (6)0.0148 (3)
H450.0299881.3034900.0575640.018*
C460.00035 (19)1.0516 (2)0.11251 (6)0.0130 (3)
H460.0806081.1193000.1387570.016*
N20.14883 (17)0.7093 (2)0.26448 (5)0.0126 (3)
N30.07176 (17)0.8271 (2)0.21740 (5)0.0121 (3)
H30.016 (3)0.937 (4)0.2235 (8)0.015*
N40.26201 (19)1.1754 (3)0.02341 (6)0.0204 (3)
O50.05660 (14)0.51366 (18)0.16611 (5)0.0159 (3)
O410.35840 (18)1.0753 (2)0.05869 (5)0.0294 (3)
O420.2243 (2)1.3682 (2)0.02764 (6)0.0372 (4)
S10.34971 (5)1.06971 (6)0.27249 (2)0.01503 (15)
S20.38495 (5)0.70489 (6)0.35298 (2)0.01385 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0143 (7)0.0106 (7)0.0097 (7)0.0021 (5)0.0033 (5)0.0013 (5)
C40.0098 (6)0.0124 (8)0.0131 (7)0.0009 (5)0.0014 (5)0.0001 (5)
C110.0147 (7)0.0170 (8)0.0150 (8)0.0036 (6)0.0005 (6)0.0009 (6)
C210.0136 (7)0.0187 (8)0.0142 (7)0.0007 (6)0.0010 (5)0.0009 (6)
C410.0116 (7)0.0118 (7)0.0114 (7)0.0022 (6)0.0016 (5)0.0023 (6)
C420.0139 (7)0.0132 (7)0.0145 (8)0.0003 (6)0.0010 (6)0.0033 (6)
C430.0139 (7)0.0200 (8)0.0133 (7)0.0014 (6)0.0003 (6)0.0054 (6)
C440.0182 (8)0.0184 (8)0.0095 (7)0.0065 (6)0.0027 (6)0.0002 (6)
C450.0183 (7)0.0129 (7)0.0137 (7)0.0024 (6)0.0039 (6)0.0008 (6)
C460.0127 (7)0.0136 (7)0.0125 (7)0.0008 (5)0.0007 (5)0.0026 (5)
N20.0150 (6)0.0109 (6)0.0112 (6)0.0013 (5)0.0009 (5)0.0016 (4)
N30.0141 (6)0.0092 (6)0.0117 (6)0.0027 (5)0.0025 (5)0.0003 (5)
N40.0245 (7)0.0242 (8)0.0118 (7)0.0085 (6)0.0006 (6)0.0001 (5)
O50.0188 (5)0.0100 (5)0.0183 (5)0.0016 (4)0.0012 (4)0.0016 (4)
O410.0295 (7)0.0378 (8)0.0174 (6)0.0012 (6)0.0091 (5)0.0013 (5)
O420.0618 (10)0.0229 (7)0.0226 (7)0.0040 (7)0.0088 (6)0.0070 (5)
S10.0165 (2)0.0136 (2)0.0141 (2)0.00375 (13)0.00081 (15)0.00427 (12)
S20.0150 (2)0.0144 (2)0.0112 (2)0.00060 (13)0.00138 (15)0.00337 (12)
Geometric parameters (Å, º) top
C1—N21.283 (2)C41—C421.400 (2)
C1—S21.7553 (15)C42—C431.387 (2)
C1—S11.7560 (15)C42—H420.9300
C4—O51.2247 (19)C43—C441.385 (2)
C4—N31.363 (2)C43—H430.9300
C4—C411.501 (2)C44—C451.384 (2)
C11—C211.518 (2)C44—N41.473 (2)
C11—S11.8172 (16)C45—C461.395 (2)
C11—H11A0.9700C45—H450.9300
C11—H11B0.9700C46—H460.9300
C21—S21.8170 (16)N2—N31.4179 (17)
C21—H21A0.9700N3—H30.83 (2)
C21—H21B0.9700N4—O421.226 (2)
C41—C461.392 (2)N4—O411.227 (2)
N2—C1—S2119.82 (12)C41—C42—H42120.0
N2—C1—S1125.06 (12)C44—C43—C42118.20 (14)
S2—C1—S1115.12 (9)C44—C43—H43120.9
O5—C4—N3124.13 (14)C42—C43—H43120.9
O5—C4—C41121.19 (14)C45—C44—C43123.26 (15)
N3—C4—C41114.50 (13)C45—C44—N4118.37 (14)
C21—C11—S1108.17 (11)C43—C44—N4118.36 (14)
C21—C11—H11A110.1C44—C45—C46117.95 (14)
S1—C11—H11A110.1C44—C45—H45121.0
C21—C11—H11B110.1C46—C45—H45121.0
S1—C11—H11B110.1C41—C46—C45120.15 (14)
H11A—C11—H11B108.4C41—C46—H46119.9
C11—C21—S2108.16 (10)C45—C46—H46119.9
C11—C21—H21A110.1C1—N2—N3111.72 (12)
S2—C21—H21A110.1C4—N3—N2116.21 (12)
C11—C21—H21B110.1C4—N3—H3120.3 (14)
S2—C21—H21B110.1N2—N3—H3116.3 (14)
H21A—C21—H21B108.4O42—N4—O41123.72 (14)
C46—C41—C42120.37 (14)O42—N4—C44118.15 (14)
C46—C41—C4121.60 (13)O41—N4—C44118.13 (14)
C42—C41—C4117.84 (14)C1—S1—C1196.17 (7)
C43—C42—C41120.05 (15)C1—S2—C2194.42 (7)
C43—C42—H42120.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···N2i0.83 (2)2.16 (2)2.9843 (19)175 (2)
Symmetry code: (i) x, y+1/2, z+1/2.
(I4) top
Crystal data top
C10H9N3O3S2·H2OF(000) = 624
Mr = 301.34Dx = 1.626 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54178 Å
a = 7.3654 (3) ÅCell parameters from 9981 reflections
b = 6.4550 (2) Åθ = 3.4–72.5°
c = 25.8911 (9) ŵ = 4.09 mm1
β = 90.808 (1)°T = 100 K
V = 1230.84 (8) Å3Plate, colourless
Z = 40.60 × 0.46 × 0.03 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
2406 reflections with I > 2σ(I)
ω scanRint = 0.029
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
θmax = 72.5°, θmin = 3.4°
Tmin = 0.507, Tmax = 0.754h = 99
13701 measured reflectionsk = 76
2423 independent reflectionsl = 3132
Refinement top
Refinement on F23 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.026H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.069 w = 1/[σ2(Fo2) + (0.032P)2 + 0.9597P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.002
2423 reflectionsΔρmax = 0.53 e Å3
181 parametersΔρmin = 0.26 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
C10.49542 (16)0.7865 (2)0.72028 (5)0.0116 (2)
N20.47914 (15)0.72085 (17)0.67374 (4)0.0141 (2)
N30.56255 (15)0.84599 (18)0.63652 (4)0.0129 (2)
H30.546 (2)0.977 (3)0.6387 (7)0.015*
C40.60402 (17)0.7527 (2)0.59136 (5)0.0127 (3)
O50.58811 (15)0.56561 (15)0.58418 (4)0.0215 (2)
C410.67658 (16)0.8897 (2)0.54942 (5)0.0111 (2)
C420.68418 (17)0.8029 (2)0.50001 (5)0.0127 (3)
H420.6445570.6677560.4946000.015*
C430.75040 (17)0.9172 (2)0.45911 (5)0.0132 (3)
H430.7559570.8604020.4261530.016*
C440.80809 (16)1.1178 (2)0.46848 (5)0.0118 (3)
C450.80235 (17)1.2094 (2)0.51684 (5)0.0130 (3)
H450.8415771.3449050.5219140.016*
C460.73622 (17)1.0925 (2)0.55751 (5)0.0127 (3)
H460.7316401.1498940.5904160.015*
N40.88001 (15)1.23893 (18)0.42488 (4)0.0149 (2)
O410.90489 (15)1.14833 (16)0.38404 (4)0.0242 (2)
O420.91342 (15)1.42324 (16)0.43183 (4)0.0242 (2)
S10.62612 (4)0.99731 (5)0.74193 (2)0.01691 (10)
S20.38078 (4)0.65196 (5)0.76904 (2)0.01598 (10)
C110.5457 (2)0.9915 (2)0.80762 (6)0.0244 (3)
H11A0.6375061.0478980.8308870.029*
H11B0.4367931.0750010.8104460.029*
C210.5053 (2)0.7706 (3)0.82192 (5)0.0234 (3)
H21A0.4337590.7665110.8530700.028*
H21B0.6176410.6959480.8283710.028*
O1W0.45304 (15)0.26144 (15)0.64596 (4)0.0213 (2)
H2W0.444 (3)0.298 (3)0.6759 (4)0.032*
H1W0.487 (3)0.366 (2)0.6314 (6)0.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0120 (6)0.0117 (6)0.0111 (6)0.0001 (5)0.0018 (5)0.0009 (5)
N20.0192 (6)0.0120 (5)0.0110 (5)0.0019 (4)0.0035 (4)0.0012 (4)
N30.0200 (6)0.0086 (5)0.0102 (5)0.0014 (4)0.0031 (4)0.0010 (4)
C40.0142 (6)0.0126 (6)0.0115 (6)0.0011 (5)0.0013 (5)0.0006 (5)
O50.0384 (6)0.0109 (5)0.0155 (5)0.0013 (4)0.0108 (4)0.0007 (4)
C410.0105 (5)0.0120 (6)0.0109 (6)0.0019 (5)0.0007 (4)0.0012 (5)
C420.0144 (6)0.0106 (6)0.0130 (6)0.0006 (5)0.0008 (5)0.0008 (5)
C430.0150 (6)0.0138 (6)0.0107 (6)0.0018 (5)0.0011 (5)0.0016 (5)
C440.0103 (6)0.0138 (6)0.0114 (6)0.0009 (5)0.0015 (4)0.0034 (5)
C450.0129 (6)0.0116 (6)0.0144 (6)0.0009 (5)0.0001 (5)0.0001 (5)
C460.0138 (6)0.0142 (6)0.0101 (6)0.0001 (5)0.0000 (5)0.0016 (5)
N40.0154 (5)0.0162 (6)0.0130 (5)0.0005 (4)0.0014 (4)0.0031 (4)
O410.0376 (6)0.0224 (6)0.0127 (5)0.0028 (4)0.0082 (4)0.0008 (4)
O420.0352 (6)0.0164 (5)0.0211 (5)0.0079 (4)0.0047 (4)0.0031 (4)
S10.01991 (18)0.01910 (19)0.01174 (17)0.00822 (12)0.00094 (12)0.00152 (12)
S20.01892 (18)0.01772 (19)0.01142 (17)0.00419 (12)0.00424 (12)0.00176 (12)
C110.0313 (8)0.0307 (9)0.0111 (7)0.0074 (6)0.0022 (6)0.0067 (6)
C210.0252 (7)0.0337 (8)0.0112 (7)0.0021 (6)0.0014 (5)0.0007 (6)
O1W0.0377 (6)0.0112 (5)0.0153 (5)0.0013 (4)0.0088 (4)0.0007 (4)
Geometric parameters (Å, º) top
C1—N21.2814 (17)C44—N41.4775 (16)
C1—S11.7543 (13)C45—C461.3891 (18)
C1—S21.7582 (13)C45—H450.9300
N2—N31.4054 (15)C46—H460.9300
N3—C41.3540 (17)N4—O411.2243 (15)
N3—H30.858 (18)N4—O421.2277 (16)
C4—O51.2270 (17)S1—C111.8092 (15)
C4—C411.5047 (17)S2—C211.8075 (15)
C41—C461.3954 (19)C11—C211.504 (2)
C41—C421.3984 (18)C11—H11A0.9700
C42—C431.3849 (18)C11—H11B0.9700
C42—H420.9300C21—H21A0.9700
C43—C441.3836 (19)C21—H21B0.9700
C43—H430.9300O1W—H2W0.814 (9)
C44—C451.3858 (18)O1W—H1W0.814 (9)
N2—C1—S1126.92 (10)C44—C45—H45121.0
N2—C1—S2118.19 (10)C46—C45—H45121.0
S1—C1—S2114.87 (7)C45—C46—C41120.57 (12)
C1—N2—N3114.75 (11)C45—C46—H46119.7
C4—N3—N2116.26 (11)C41—C46—H46119.7
C4—N3—H3122.0 (12)O41—N4—O42123.88 (12)
N2—N3—H3117.3 (11)O41—N4—C44117.82 (11)
O5—C4—N3123.12 (12)O42—N4—C44118.29 (11)
O5—C4—C41120.23 (11)C1—S1—C1195.68 (7)
N3—C4—C41116.63 (11)C1—S2—C2195.21 (7)
C46—C41—C42119.78 (12)C21—C11—S1108.63 (10)
C46—C41—C4123.88 (11)C21—C11—H11A110.0
C42—C41—C4116.33 (11)S1—C11—H11A110.0
C43—C42—C41120.34 (12)C21—C11—H11B110.0
C43—C42—H42119.8S1—C11—H11B110.0
C41—C42—H42119.8H11A—C11—H11B108.3
C44—C43—C42118.36 (12)C11—C21—S2108.38 (10)
C44—C43—H43120.8C11—C21—H21A110.0
C42—C43—H43120.8S2—C21—H21A110.0
C43—C44—C45122.99 (12)C11—C21—H21B110.0
C43—C44—N4118.28 (11)S2—C21—H21B110.0
C45—C44—N4118.72 (12)H21A—C21—H21B108.4
C44—C45—C46117.96 (12)H2W—O1W—H1W103.4 (16)
S1—C1—N2—N36.44 (17)N4—C44—C45—C46179.30 (11)
S2—C1—N2—N3175.08 (9)C44—C45—C46—C410.42 (19)
C1—N2—N3—C4157.92 (12)C42—C41—C46—C450.30 (19)
N2—N3—C4—O57.15 (19)C4—C41—C46—C45179.70 (11)
N2—N3—C4—C41174.25 (10)C43—C44—N4—O418.38 (17)
O5—C4—C41—C46165.43 (13)C45—C44—N4—O41171.26 (12)
N3—C4—C41—C4613.21 (18)C43—C44—N4—O42172.52 (12)
O5—C4—C41—C4213.98 (18)C45—C44—N4—O427.85 (18)
N3—C4—C41—C42167.38 (11)N2—C1—S1—C11173.37 (13)
C46—C41—C42—C430.05 (19)S2—C1—S1—C118.11 (9)
C4—C41—C42—C43179.49 (11)N2—C1—S2—C21165.37 (11)
C41—C42—C43—C440.06 (19)S1—C1—S2—C2113.28 (9)
C42—C43—C44—C450.08 (19)C1—S1—C11—C2132.19 (12)
C42—C43—C44—N4179.54 (11)S1—C11—C21—S245.10 (13)
C43—C44—C45—C460.32 (19)C1—S2—C21—C1135.18 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···O50.81 (1)1.93 (1)2.7291 (14)166 (2)
O1W—H1W···N20.81 (1)2.54 (2)3.0569 (15)123 (2)
N3—H3···O1Wi0.858 (18)1.968 (19)2.8120 (15)167.6 (16)
Symmetry code: (i) x, y+1, z.
Torsion angles top
C1—N2—N3—C4O5—C4—C41—C42
I1153.60 (13)34.5 (2)
I2150.23 (13)33.1 (2)
I3139.33 (15)35.0 (2)
I4157.69 (12)13.96 (19)
 

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