1-(2-Hy­droxy­benzo­yl)thio­semicarbazide hemihydrate

Song, M.; Fan, C.

doi:10.1107/S1600536810044259

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3048

https://doi.org/10.1107/S1600536810044259

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1-(2-Hydroxybenzoyl)thiosemicarbazide hemihydrate

Ming-zhi Song ^a ^* and Chuangang Fan ^a

^aCollege of Chemistry and Chemical Technology, Binzhou University, Binzhou 256600, Shandong, People's Republic of China
^*Correspondence e-mail: fanchuangang2009@163.com

(Received 14 October 2010; accepted 29 October 2010; online 6 November 2010)

The asymmetric unit of the title compound, C₈H₉N₃O₂S·0.5H₂O, contains two thiosemicarbazide molecules with the short distance of 3.521 (3) Å between the centroids of the benzene rings, and one water molecule. In the two independent molecules, the benzene rings and the thiosemicarbazone fragments are twisted at 9.2 (3) and 18.5 (3)°. An extensive three-dimensional hydrogen-bonding network, formed by intermolecular N—H⋯O, N—H⋯S and O—H⋯O hydrogen bonds, consolidates the crystal packing.

Related literature

For the biological activities of thiosemicarbazide derivatives, see: Desai et al. (1984 ); Shukla et al. (1984 ). For related structures, see: Gors et al. (1979 ); Jin (2007 ).

Experimental

Crystal data

C₈H₉N₃O₂S·0.5H₂O
M_r = 440.50
Monoclinic, P 2₁ /n
a = 9.0718 (11) Å
b = 21.608 (2) Å
c = 10.1035 (13) Å
β = 90.173 (1)°
V = 1980.5 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 298 K
0.45 × 0.20 × 0.17 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.873, T_max = 0.949
9862 measured reflections
3487 independent reflections
2202 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.122
S = 1.01
3487 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯S1ⁱ	0.86	2.58	3.361 (3)	151
N5—H5⋯S1ⁱⁱ	0.86	2.83	3.404 (3)	125
N6—H6A⋯O2ⁱⁱⁱ	0.86	2.16	2.984 (3)	160
N6—H6B⋯S2^iv	0.86	2.85	3.647 (3)	156
O4—H4⋯O1ⁱⁱ	0.82	1.93	2.724 (3)	162
O5—H5B⋯O5^v	0.85	1.95	2.728 (10)	152
N3—H3A⋯O3	0.86	2.12	2.918 (3)	154
N3—H3B⋯O5	0.86	2.30	3.110 (5)	156
N5—H5⋯O4	0.86	1.99	2.629 (3)	130
O2—H2A⋯O1	0.82	1.83	2.552 (3)	146
O5—H5D⋯S1	0.85	2.66	3.398 (4)	147
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x+1, y, z; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) -x+2, -y, -z; (v) -x+1, -y, -z.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810044259/cv2777sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810044259/cv2777Isup2.hkl

checkCIF report

Comment top

Thiosemicarbazide compounds exhibit various biological activities such as anti-bacterial, anti-fungal and especially anti-tuberculosis (Shukla et al., 1984; Desai et al., 1984). Herewith we present the title compound (I), a new thiosemicarbazide compound.

The asymmetric unit of (I) contains two independent molecules and one crystalline water molecule (Fig. 1). The bond lengths and angles are normal and comparable to the values observed in similar compounds (Gors et al., 1979; Jin, 2007). In two independent molecules, the benzene rings and the thiosemicarbazone fragments (C/N/N) are twisted at 9.2 (3)° and 18.5 (3)°, respectively.

In the crystal structure, the three-dimensional network structure was formed by the intermolecular N—H···O, N—H···S and O—H···O hydrogen bonds (Table 1).

Related literature top

For the biological activities of thiosemicarbazide derivatives, see: Desai et al. (1984); Shukla et al. (1984). For the crystal structures of related compounds, see: Gors et al. (1979); Jin (2007).

Experimental top

Salicylyl hydrazine (10 mmol), potassium thiocyanate (12 mmol) and 10 ml me thanol-water (1:1) were mixed in 50 ml flask. After refluxing 12 h at 373 K, the resulting mixture was recrystalized from solution, affording the title compound as a colorless crystalline solid.

Structure description top

In the crystal structure, the three-dimensional network structure was formed by the intermolecular N—H···O, N—H···S and O—H···O hydrogen bonds (Table 1).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The content of asymmetric unit of the title compound showing the atomic numbering scheme and 30% probability displacement ellipsoids.

1-(2-Hydroxybenzoyl)thiosemicarbazide hemihydrate top

Crystal data top

C₁₆H₂₀N₆O₅S₂	F(000) = 916
M_r = 440.50	D_x = 1.474 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.0718 (11) Å	Cell parameters from 2367 reflections
b = 21.608 (2) Å	θ = 2.2–25.7°
c = 10.1035 (13) Å	µ = 0.31 mm⁻¹
β = 90.173 (1)°	T = 298 K
V = 1980.5 (4) Å³	Block, yellow
Z = 4	0.45 × 0.20 × 0.17 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3487 independent reflections
Radiation source: fine-focus sealed tube	2202 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
φ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.873, T_max = 0.949	k = −21→25
9862 measured reflections	l = −11→12

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0468P)² + 1.2463P] where P = (F_o² + 2F_c²)/3
3487 reflections	(Δ/σ)_max < 0.001
262 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₆H₂₀N₆O₅S₂	V = 1980.5 (4) Å³
M_r = 440.50	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.0718 (11) Å	µ = 0.31 mm⁻¹
b = 21.608 (2) Å	T = 298 K
c = 10.1035 (13) Å	0.45 × 0.20 × 0.17 mm
β = 90.173 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3487 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2202 reflections with I > 2σ(I)
T_min = 0.873, T_max = 0.949	R_int = 0.041
9862 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.01	Δρ_max = 0.37 e Å⁻³
3487 reflections	Δρ_min = −0.33 e Å⁻³
262 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	0.4021 (3)	0.07227 (12)	0.5682 (3)	0.0401 (7)
H1	0.3330	0.0634	0.6231	0.048*
N2	0.5273 (3)	0.10117 (11)	0.6152 (3)	0.0392 (7)
H2	0.6033	0.0794	0.6354	0.047*
N3	0.4849 (3)	0.07466 (12)	0.3544 (3)	0.0443 (7)
H3A	0.5612	0.0950	0.3806	0.053*
H3B	0.4746	0.0655	0.2721	0.053*
N4	0.8800 (3)	0.06010 (11)	0.3372 (3)	0.0399 (7)
H4'	0.8275	0.0385	0.3908	0.048*
N5	0.9398 (3)	0.11556 (11)	0.3803 (3)	0.0362 (7)
H5	1.0322	0.1177	0.3992	0.043*
N6	0.9674 (3)	0.07614 (13)	0.1292 (3)	0.0527 (8)
H6A	0.9949	0.1125	0.1534	0.063*
H6B	0.9827	0.0639	0.0495	0.063*
O1	0.4251 (2)	0.19444 (10)	0.5943 (2)	0.0386 (6)
O2	0.5712 (3)	0.29296 (10)	0.6415 (2)	0.0441 (6)
H2A	0.5042	0.2722	0.6100	0.066*
O3	0.7237 (2)	0.16510 (10)	0.3629 (2)	0.0439 (6)
O4	1.1396 (2)	0.17295 (9)	0.5240 (2)	0.0408 (6)
H4	1.2180	0.1806	0.5612	0.061*
O5	0.3935 (7)	0.0087 (2)	0.0932 (4)	0.172 (2)
H5D	0.3575	−0.0063	0.1638	0.206*	0.50
H5B	0.4780	0.0030	0.0591	0.206*	0.50
S1	0.23175 (9)	0.01686 (4)	0.39559 (9)	0.0415 (3)
S2	0.84286 (14)	−0.03260 (5)	0.17448 (11)	0.0703 (4)
C1	0.3839 (4)	0.05757 (13)	0.4406 (3)	0.0336 (8)
C2	0.5320 (3)	0.16295 (14)	0.6297 (3)	0.0307 (7)
C3	0.6647 (3)	0.19040 (13)	0.6870 (3)	0.0287 (7)
C4	0.6763 (3)	0.25507 (14)	0.6910 (3)	0.0315 (7)
C5	0.7998 (4)	0.28273 (16)	0.7474 (3)	0.0404 (8)
H5A	0.8066	0.3256	0.7513	0.049*
C6	0.9113 (4)	0.24687 (18)	0.7971 (3)	0.0448 (9)
H6	0.9938	0.2657	0.8342	0.054*
C7	0.9031 (4)	0.18322 (17)	0.7929 (3)	0.0445 (9)
H7	0.9797	0.1593	0.8267	0.053*
C8	0.7813 (3)	0.15549 (15)	0.7387 (3)	0.0377 (8)
H8	0.7761	0.1125	0.7361	0.045*
C9	0.9021 (4)	0.03945 (15)	0.2138 (4)	0.0412 (8)
C10	0.8546 (3)	0.16613 (14)	0.3929 (3)	0.0307 (7)
C11	0.9288 (3)	0.22405 (13)	0.4381 (3)	0.0288 (7)
C12	1.0660 (3)	0.22665 (13)	0.5004 (3)	0.0303 (7)
C13	1.1241 (4)	0.28340 (14)	0.5386 (3)	0.0370 (8)
H13	1.2142	0.2849	0.5826	0.044*
C14	1.0501 (4)	0.33711 (15)	0.5122 (3)	0.0425 (9)
H14	1.0910	0.3749	0.5365	0.051*
C15	0.9147 (4)	0.33536 (15)	0.4495 (3)	0.0431 (9)
H15	0.8642	0.3719	0.4314	0.052*
C16	0.8552 (4)	0.27936 (14)	0.4143 (3)	0.0373 (8)
H16	0.7633	0.2784	0.3733	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0370 (17)	0.0357 (16)	0.0475 (18)	−0.0102 (13)	−0.0024 (14)	−0.0063 (14)
N2	0.0284 (16)	0.0278 (15)	0.0613 (19)	−0.0024 (12)	−0.0136 (13)	−0.0030 (13)
N3	0.0396 (18)	0.0449 (17)	0.0485 (18)	−0.0078 (14)	−0.0004 (15)	−0.0042 (14)
N4	0.0388 (17)	0.0296 (15)	0.0514 (18)	−0.0092 (12)	0.0036 (14)	−0.0057 (13)
N5	0.0256 (15)	0.0272 (14)	0.0558 (18)	−0.0054 (12)	−0.0035 (13)	−0.0093 (13)
N6	0.078 (2)	0.0351 (17)	0.0453 (18)	−0.0171 (16)	0.0066 (16)	−0.0064 (15)
O1	0.0281 (13)	0.0323 (12)	0.0555 (14)	0.0039 (10)	−0.0091 (11)	−0.0004 (11)
O2	0.0432 (15)	0.0294 (12)	0.0596 (15)	0.0017 (10)	−0.0031 (12)	−0.0032 (11)
O3	0.0241 (13)	0.0436 (14)	0.0639 (16)	−0.0005 (10)	−0.0073 (11)	−0.0033 (12)
O4	0.0315 (13)	0.0331 (13)	0.0577 (15)	0.0027 (10)	−0.0120 (11)	−0.0027 (11)
O5	0.299 (7)	0.114 (3)	0.102 (3)	−0.017 (4)	0.030 (4)	−0.006 (3)
S1	0.0350 (5)	0.0327 (5)	0.0567 (6)	−0.0036 (4)	−0.0089 (4)	−0.0056 (4)
S2	0.1012 (9)	0.0420 (6)	0.0677 (7)	−0.0309 (6)	0.0138 (6)	−0.0172 (5)
C1	0.0309 (19)	0.0198 (16)	0.050 (2)	0.0055 (13)	−0.0033 (16)	−0.0016 (15)
C2	0.0303 (18)	0.0316 (18)	0.0302 (17)	−0.0006 (15)	0.0035 (14)	0.0010 (14)
C3	0.0264 (17)	0.0303 (17)	0.0293 (17)	−0.0022 (13)	0.0012 (13)	−0.0030 (14)
C4	0.0308 (19)	0.0325 (18)	0.0313 (18)	0.0019 (14)	0.0051 (14)	−0.0033 (15)
C5	0.041 (2)	0.0376 (19)	0.043 (2)	−0.0130 (16)	0.0075 (17)	−0.0115 (16)
C6	0.030 (2)	0.064 (3)	0.040 (2)	−0.0169 (18)	0.0041 (16)	−0.0147 (19)
C7	0.030 (2)	0.058 (2)	0.045 (2)	−0.0004 (17)	−0.0064 (16)	−0.0021 (18)
C8	0.036 (2)	0.0357 (19)	0.0410 (19)	0.0022 (15)	−0.0036 (16)	−0.0021 (16)
C9	0.040 (2)	0.0313 (19)	0.052 (2)	−0.0035 (15)	−0.0020 (17)	−0.0036 (17)
C10	0.0270 (19)	0.0315 (18)	0.0337 (18)	−0.0003 (14)	0.0046 (14)	0.0012 (14)
C11	0.0253 (17)	0.0284 (17)	0.0328 (17)	−0.0003 (13)	0.0068 (14)	−0.0011 (14)
C12	0.0288 (18)	0.0285 (17)	0.0338 (18)	0.0000 (14)	0.0034 (14)	−0.0009 (14)
C13	0.0326 (19)	0.0354 (19)	0.043 (2)	−0.0050 (15)	0.0012 (16)	−0.0043 (16)
C14	0.048 (2)	0.0285 (19)	0.051 (2)	−0.0053 (17)	0.0093 (18)	−0.0096 (16)
C15	0.046 (2)	0.0274 (18)	0.056 (2)	0.0080 (16)	0.0064 (18)	0.0025 (16)
C16	0.034 (2)	0.0360 (19)	0.042 (2)	0.0057 (15)	0.0076 (15)	0.0017 (16)

Geometric parameters (Å, º) top

N1—C1	1.338 (4)	S1—C1	1.697 (3)
N1—N2	1.379 (3)	S2—C9	1.694 (3)
N1—H1	0.8600	C2—C3	1.460 (4)
N2—C2	1.344 (4)	C3—C8	1.399 (4)
N2—H2	0.8600	C3—C4	1.402 (4)
N3—C1	1.319 (4)	C4—C5	1.391 (4)
N3—H3A	0.8600	C5—C6	1.369 (5)
N3—H3B	0.8600	C5—H5A	0.9300
N4—C9	1.340 (4)	C6—C7	1.378 (5)
N4—N5	1.385 (3)	C6—H6	0.9300
N4—H4'	0.8600	C7—C8	1.370 (4)
N5—C10	1.345 (4)	C7—H7	0.9300
N5—H5	0.8600	C8—H8	0.9300
N6—C9	1.308 (4)	C10—C11	1.492 (4)
N6—H6A	0.8600	C11—C16	1.390 (4)
N6—H6B	0.8600	C11—C12	1.394 (4)
O1—C2	1.237 (3)	C12—C13	1.389 (4)
O2—C4	1.351 (4)	C13—C14	1.367 (4)
O2—H2A	0.8200	C13—H13	0.9300
O3—C10	1.225 (3)	C14—C15	1.381 (5)
O4—C12	1.359 (3)	C14—H14	0.9300
O4—H4	0.8200	C15—C16	1.371 (4)
O5—H5D	0.8496	C15—H15	0.9300
O5—H5B	0.8500	C16—H16	0.9300

C1—N1—N2	122.6 (3)	C4—C5—H5A	120.0
C1—N1—H1	118.7	C5—C6—C7	120.9 (3)
N2—N1—H1	118.7	C5—C6—H6	119.5
C2—N2—N1	120.9 (3)	C7—C6—H6	119.5
C2—N2—H2	119.5	C8—C7—C6	119.5 (3)
N1—N2—H2	119.5	C8—C7—H7	120.3
C1—N3—H3A	120.0	C6—C7—H7	120.3
C1—N3—H3B	120.0	C7—C8—C3	121.4 (3)
H3A—N3—H3B	120.0	C7—C8—H8	119.3
C9—N4—N5	121.4 (3)	C3—C8—H8	119.3
C9—N4—H4'	119.3	N6—C9—N4	118.4 (3)
N5—N4—H4'	119.3	N6—C9—S2	123.2 (3)
C10—N5—N4	120.5 (3)	N4—C9—S2	118.4 (3)
C10—N5—H5	119.7	O3—C10—N5	121.3 (3)
N4—N5—H5	119.7	O3—C10—C11	121.8 (3)
C9—N6—H6A	120.0	N5—C10—C11	116.8 (3)
C9—N6—H6B	120.0	C16—C11—C12	118.1 (3)
H6A—N6—H6B	120.0	C16—C11—C10	116.9 (3)
C4—O2—H2A	109.5	C12—C11—C10	125.0 (3)
C12—O4—H4	109.5	O4—C12—C13	121.3 (3)
H5D—O5—H5B	129.4	O4—C12—C11	118.8 (3)
N3—C1—N1	119.1 (3)	C13—C12—C11	119.9 (3)
N3—C1—S1	122.3 (3)	C14—C13—C12	120.6 (3)
N1—C1—S1	118.6 (3)	C14—C13—H13	119.7
O1—C2—N2	119.4 (3)	C12—C13—H13	119.7
O1—C2—C3	122.4 (3)	C13—C14—C15	120.2 (3)
N2—C2—C3	118.2 (3)	C13—C14—H14	119.9
C8—C3—C4	118.1 (3)	C15—C14—H14	119.9
C8—C3—C2	123.4 (3)	C16—C15—C14	119.5 (3)
C4—C3—C2	118.5 (3)	C16—C15—H15	120.3
O2—C4—C5	117.2 (3)	C14—C15—H15	120.3
O2—C4—C3	122.7 (3)	C15—C16—C11	121.7 (3)
C5—C4—C3	120.0 (3)	C15—C16—H16	119.2
C6—C5—C4	120.1 (3)	C11—C16—H16	119.2
C6—C5—H5A	120.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S1ⁱ	0.86	2.58	3.361 (3)	151
N5—H5···S1ⁱⁱ	0.86	2.83	3.404 (3)	125
N6—H6A···O2ⁱⁱⁱ	0.86	2.16	2.984 (3)	160
N6—H6B···S2^iv	0.86	2.85	3.647 (3)	156
O4—H4···O1ⁱⁱ	0.82	1.93	2.724 (3)	162
O5—H5B···O5^v	0.85	1.95	2.728 (10)	152
N3—H3A···O3	0.86	2.12	2.918 (3)	154
N3—H3B···O5	0.86	2.30	3.110 (5)	156
N5—H5···O4	0.86	1.99	2.629 (3)	130
O2—H2A···O1	0.82	1.83	2.552 (3)	146
O5—H5D···S1	0.85	2.66	3.398 (4)	147

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

Experimental details

Crystal data
Chemical formula	C₁₆H₂₀N₆O₅S₂
M_r	440.50
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	9.0718 (11), 21.608 (2), 10.1035 (13)
β (°)	90.173 (1)
V (Å³)	1980.5 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.45 × 0.20 × 0.17

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.873, 0.949
No. of measured, independent and observed [I > 2σ(I)] reflections	9862, 3487, 2202
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.122, 1.01
No. of reflections	3487
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.33

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S1ⁱ	0.86	2.58	3.361 (3)	151.4
N5—H5···S1ⁱⁱ	0.86	2.83	3.404 (3)	125.4
N6—H6A···O2ⁱⁱⁱ	0.86	2.16	2.984 (3)	160.3
N6—H6B···S2^iv	0.86	2.85	3.647 (3)	155.5
O4—H4···O1ⁱⁱ	0.82	1.93	2.724 (3)	162.3
O5—H5B···O5^v	0.85	1.95	2.728 (10)	151.7
N3—H3A···O3	0.86	2.12	2.918 (3)	153.7
N3—H3B···O5	0.86	2.30	3.110 (5)	156.3
N5—H5···O4	0.86	1.99	2.629 (3)	130.3
O2—H2A···O1	0.82	1.83	2.552 (3)	145.6
O5—H5D···S1	0.85	2.66	3.398 (4)	146.7

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

Acknowledgements

The authors acknowledge the financial support of the Foundation of Binzhou University (grant No. BZXYQNLG200501).

References

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