1-(4-Ethoxy­benzo­yl)-4-(4-methoxy­phen­yl)thiosemicarbazide

Khanum, S.; Farman, M.; Rama, N.H.; Hameed, S.; Jones, P.G.

doi:10.1107/S1600536809036599

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 11| November 2009| Pages o2604-o2605

https://doi.org/10.1107/S1600536809036599

Open

access

1-(4-Ethoxybenzoyl)-4-(4-methoxyphenyl)thiosemicarbazide

Saira Khanum,^a Muhammad Farman,^a ^* Nasim H. Rama,^a Shahid Hameed ^a and Peter G. Jones ^b

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad-45320, Pakistan, and ^bInstitut für Anorganische und Analytische Chemie, Technische Universität Braunschweig, Postfach 3329, 38023 Braunschweig, Germany
^*Correspondence e-mail: farman@qau.edu.pk

(Received 9 September 2009; accepted 10 September 2009; online 3 October 2009)

The title compound, C₁₇H₁₉N₃O₃S, crystallizes with two closely similar independent molecules related by a pseudotranslation of c/2. Each molecule consists of three approximately planar moieties centred on the N₂CS group and the two ring systems. The packing involves classical H bonds of the form N_amide—H⋯S and N_hydrazine—H⋯OC, together with various weak hydrogen bonds and N_hydrazine—H⋯π interactions. The overall packing is three-dimensional, but layer substructures parallel to the xz plane can be readily identified. Each molecule forms a topologically equivalent set of hydrogen-bond interactions.

Related literature

Thiosemicarbazides represent a class of versatile precursors for the syntheses of various nitrogen heterocycles, see: Al-Masoudi et al. (2006 ); Kucukguzel et al. (2007 ); Serwar et al.2009 ); Serwer et al. (2008 ); Tomascikava et al. (2008 ); Tozkoparan et al. (2007 ). For the pharmaceutical potential of the thiosemicarbazide moiety, see: Angelusiu et al. (2009 ); Ghosh et al. (2009 ); Liu et al. (2009 ).

Experimental

Crystal data

C₁₇H₁₉N₃O₃S
M_r = 345.41
Monoclinic, P 2₁
a = 15.40429 (13) Å
b = 9.67120 (9) Å
c = 11.69922 (9) Å
β = 95.0922 (7)°
V = 1736.05 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 100 K
0.3 × 0.2 × 0.1 mm

Data collection

Oxford Diffraction Xcalibur E diffractometer
Absorption correction: multi-scan (CrysAlisPro; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction Ltd., Yarnton, Oxford, UK.]$ ) T_min = 0.981, T_max = 1.000
44704 measured reflections
9918 independent reflections
6348 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.055
S = 0.96
9918 reflections
461 parameters
16 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ), 4562 Friedel pairs
Flack parameter: 0.01 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H01⋯S′	0.826 (11)	2.735 (12)	3.4483 (14)	145.5 (14)
N4—H04⋯O1′ⁱ	0.812 (12)	2.016 (13)	2.8156 (17)	168.2 (17)
N1′—H01′⋯Sⁱⁱ	0.816 (11)	2.659 (12)	3.3772 (14)	147.8 (14)
N4′—H04′⋯O1ⁱ	0.836 (12)	2.011 (13)	2.8228 (18)	163.7 (15)
C11′—H11′⋯O1ⁱ	0.95	2.41	3.3378 (19)	166
C11—H11⋯O1′ⁱ	0.95	2.38	3.2927 (18)	162
C20—H20B⋯Sⁱⁱⁱ	0.98	2.98	3.9215 (17)	161
C20′—H20E⋯S′^iv	0.98	2.92	3.8936 (18)	175
C10′—H10′⋯Sⁱ	0.95	2.83	3.7559 (17)	166
C10—H10⋯S′ⁱ	0.95	2.81	3.7369 (17)	166
C15′—H15′⋯Sⁱⁱ	0.95	3.05	3.6482 (16)	123
C15—H15⋯S′	0.95	2.94	3.6925 (17)	137
N3′—H03′⋯Cg	0.847 (10)	2.53	3.25	144
N3—H03⋯Cg′^v	0.822 (10)	2.65	3.29	135
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (ii) x, y, z-1; (iii) $[-x+2, y+{\script{1\over 2}}, -z+2]$ ; (iv) $[-x+2, y+{\script{1\over 2}}, -z+1]$ ; (v) x, y, z+1. Cg is the centroid of the C6–C11 ring and Cg′ is the centroid of the C6′–C11′ ring.

Data collection: CrysAlisPro (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction Ltd., Yarnton, Oxford, UK.]$ ); cell refinement: CrysAlisPro; data reduction: CrysAlisPro; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Siemens, 1994 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809036599/bt5057sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809036599/bt5057Isup2.hkl

checkCIF report

Comment top

Thiosemicarbazides represent a class of versatile precursors for the syntheses of various nitrogen heterocycles (Kucukguzel et al., 2007; Al-Masoudi et al., 2006; Tozkoparan et al., 2007; Tomascikava et al., 2008; Serwer et al. 2008; Serwar et al. 2009). The thiosemicarbazide moiety possesses substantial pharmaceutical potential such as anti-tumor (Angelusiu et al., 2009), tyrosinase inhibitor (Liu et al., 2009) and antioxidant (Ghosh et al., 2009) properties. The title compound was synthesized as an intermediate for its onward conversion to 1,2,4-triazoles and 1,3,4-thiadiazoles and in order to explore their anti-bacterial, urease inhibition and anti-fungal activities.

The title compound crystallizes with two independent molecules in the asymmetric unit (Fig. 1); these are related to a good approximation by a translation of c/2. A least-squares fit of both molecules gives an r.m.s. deviation of 0.15 Å for all non-H atoms. Main differences involve orientations of the aromatic rings, e.g. C2—N1—C14—C15 131.9 (2), 122.1 (2)°. Atoms of the second independent molecule are distinguished by a prime (') where necessary. Molecular dimensions (e.g. the hydrazine N—N bond lengths of 1.393 (2), 1.391 (2) Å) may be regarded as normal. The thione sulfur is trans to N4 across the bond C2—N3 (torsion angles 174.8 (1), 172.2 (1)°) but cis to C14 across the bond N1—C2 (torsion angles -9.0 (2), -8.1 (2)).

Each molecule consists of three approximately planar moieties with various common atoms: (1) the central thioamide section (S, N2, N3, N4, C2, C14); (2) the hydrazine and its aromatic ring (C5–13, O1, O2, N3, N4); and (3) the amide and its aromatic ring (C14–20, N1, O3). These display r.m.s. deviations of 0.07, 0.05, 0.01 Å in molecule 1 and 0.08, 0.06, 0.01 Å in molecule 2. Interplanar angles (1)–(2) and (3)–(2) are 68.09 (3), 56.56 (4)° in molecule 1 and 77.22 (3), 66.14 (3)° in molecule 2.

The molecular packing is three-dimensional; classical and "weak" hydrogen bonds are summarized in Table 2. Both molecules form a topologically equivalent set of hydrogen bonds. Fig. 2 shows that the molecules associate to form layers parallel to the xz plane; within the layers, the molecules are linked by classical H bonds N1—H01···S' (and N1'—H01'···S), whereas the layers are linked by N4—H04···O1' and the weak H bonds C10—H10···S' and C11—H11···O1' (and their counterparts). The H bond donors N3—H03 and N03'—H03' are involved in C—H···π interactions to the centroids of the ring C6'–11' and C6–11 respectively, with H···π 2.65, 2.53 Å and angles 135°, 144° respectively (operators x,y,1 + z, and x,y,z). These interactions are not shown explicitly in Fig. 2 but can be recognized within the layers.

Related literature top

Thiosemicarbazides represent a class of versatile precursors for the syntheses of various nitrogen heterocycles, see: Al-Masoudi et al. (2006); Kucukguzel et al. (2007); Serwar et al.2009); Serwer et al. (2008); Tomascikava et al. (2008); Tozkoparan et al. (2007). For the pharmaceutical potential of the thiosemicarbazide moiety, see: Angelusiu et al. (2009); Ghosh et al. (2009); Liu et al. (2009).

Experimental top

4-Ethoxybenzohydrazide (0.0068 moles) was dissolved in methanol (30 ml) and a solution of 4-methoxyphenylisothiocyanate (0.0066 moles), separately dissolved in 10 ml of methanol, was added dropwise with continuous stirring. The reaction mixture was refluxed for 10–12 h and progress of the reaction monitored by TLC. After consumption of the starting materials, the mixture was cooled to room temperature. The methanol was removed to give the crude thiosemicarbazide as an oil that solidified on cooling. The product was recrystallized from ethanol as large colourless blocks that were cut to size for X-ray analysis.

Structure description top

Thiosemicarbazides represent a class of versatile precursors for the syntheses of various nitrogen heterocycles, see: Al-Masoudi et al. (2006); Kucukguzel et al. (2007); Serwar et al.2009); Serwer et al. (2008); Tomascikava et al. (2008); Tozkoparan et al. (2007). For the pharmaceutical potential of the thiosemicarbazide moiety, see: Angelusiu et al. (2009); Ghosh et al. (2009); Liu et al. (2009).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound showing the two independent molecules, the atom labelling scheme and displacement ellipsoids at the 50% probability level.

Fig. 2. A section of the three-dimensional packing diagram of the title compound viewed parallel to the x axis. Bond types: thick continuous bonds, molecule 1; open continuous bonds, molecule 2; thick dashed bonds, classical H bonds; thin dashed bonds, C—H···O interactions. For clarity, the ethoxy substituents and all H atoms not involved in the H bonds were omitted and the rings at N1 are shown only as their ipso carbons.

1-(4-Ethoxybenzoyl)-4-(4-methoxyphenyl)thiosemicarbazide top

Crystal data top

C₁₇H₁₉N₃O₃S	F(000) = 728
M_r = 345.41	D_x = 1.322 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 15.40429 (13) Å	Cell parameters from 16506 reflections
b = 9.67120 (9) Å	θ = 2.3–30.7°
c = 11.69922 (9) Å	µ = 0.21 mm⁻¹
β = 95.0922 (7)°	T = 100 K
V = 1736.05 (3) Å³	Tablet, colourless
Z = 4	0.3 × 0.2 × 0.1 mm

Data collection top

Oxford Diffraction Xcalibur E diffractometer	9918 independent reflections
Radiation source: Enhance (Mo) X-ray Source	6348 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
Detector resolution: 16.1419 pixels mm^-1	θ_max = 30.5°, θ_min = 2.3°
ω–scan	h = −21→21
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −13→13
T_min = 0.981, T_max = 1.000	l = −15→16
44704 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.055	w = 1/[σ²(F_o²) + (0.020P)²] where P = (F_o² + 2F_c²)/3
S = 0.96	(Δ/σ)_max = 0.001
9918 reflections	Δρ_max = 0.30 e Å⁻³
461 parameters	Δρ_min = −0.23 e Å⁻³
16 restraints	Absolute structure: Flack (1983), 4562 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (3)

Crystal data top

C₁₇H₁₉N₃O₃S	V = 1736.05 (3) Å³
M_r = 345.41	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 15.40429 (13) Å	µ = 0.21 mm⁻¹
b = 9.67120 (9) Å	T = 100 K
c = 11.69922 (9) Å	0.3 × 0.2 × 0.1 mm
β = 95.0922 (7)°

Data collection top

Oxford Diffraction Xcalibur E diffractometer	9918 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	6348 reflections with I > 2σ(I)
T_min = 0.981, T_max = 1.000	R_int = 0.032
44704 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.055	Δρ_max = 0.30 e Å⁻³
S = 0.96	Δρ_min = −0.23 e Å⁻³
9918 reflections	Absolute structure: Flack (1983), 4562 Friedel pairs
461 parameters	Absolute structure parameter: 0.01 (3)
16 restraints

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

13.0283 (0.0011) x + 1.4133 (0.0037) y - 6.8581 (0.0016) z = 2.4289 (0.0026)

* 0.0169 (0.0013) C6 * 0.0162 (0.0012) C7 * 0.0312 (0.0012) C8 * 0.0483 (0.0013) C9 * 0.0676 (0.0014) C10 * 0.0481 (0.0013) C11 * 0.0436 (0.0010) O2 * -0.0206 (0.0014) C12 * -0.1392 (0.0013) C13 * 0.0011 (0.0013) C5 * -0.0780 (0.0010) O1 * 0.0952 (0.0010) N4 * -0.1306 (0.0010) N3

Rms deviation of fitted atoms = 0.0705

- 5.8835 (0.0067) x + 8.3025 (0.0025) y + 4.3848 (0.0043) z = 4.5767 (0.0054)

Angle to previous plane (with approximate e.s.d.) = 68.09 (0.03)

* -0.0909 (0.0013) N1 * -0.0296 (0.0012) C2 * 0.0247 (0.0006) S * 0.0499 (0.0008) N4 * -0.0143 (0.0011) N3 * 0.0602 (0.0008) C14

Rms deviation of fitted atoms = 0.0518

4.4124 (0.0064) x - 7.2670 (0.0036) y + 6.6294 (0.0075) z = 4.1549 (0.0063)

Angle to previous plane (with approximate e.s.d.) = 56.56 (0.04)

* 0.0131 (0.0015) C14 * 0.0077 (0.0017) C15 * -0.0154 (0.0018) C16 * 0.0007 (0.0017) C17 * -0.0065 (0.0015) C18 * -0.0105 (0.0015) C19 * -0.0002 (0.0013) O3 * 0.0099 (0.0013) C20 * 0.0012 (0.0012) N1

Rms deviation of fitted atoms = 0.0089

13.0659 (0.0012) x + 1.8489 (0.0037) y - 6.6371 (0.0017) z = 6.1077 (0.0017)

Angle to previous plane (with approximate e.s.d.) = 78.79 (0.03)

* 0.0172 (0.0013) C6' * 0.0319 (0.0011) C7' * 0.0585 (0.0011) C8' * 0.0569 (0.0013) C9' * 0.0548 (0.0014) C10' * 0.0249 (0.0013) C11' * 0.0496 (0.0010) O2' * -0.0083 (0.0015) C12' * -0.1597 (0.0014) C13' * -0.0114 (0.0013) C5' * -0.1233 (0.0010) O1' * 0.1239 (0.0010) N4' * -0.1150 (0.0010) N3'

Rms deviation of fitted atoms = 0.0802

- 4.7715 (0.0070) x + 8.8203 (0.0020) y + 3.4544 (0.0044) z = 2.9970 (0.0051)

Angle to previous plane (with approximate e.s.d.) = 77.22 (0.03)

* -0.0881 (0.0013) N1' * -0.0271 (0.0012) C2' * 0.0344 (0.0006) S' * 0.0675 (0.0008) N4' * -0.0418 (0.0011) N3' * 0.0550 (0.0008) C14'

Rms deviation of fitted atoms = 0.0563

2.1176 (0.0060) x - 6.0315 (0.0044) y + 8.8245 (0.0052) z = 0.7518 (0.0041)

Angle to previous plane (with approximate e.s.d.) = 66.14 (0.03)

* 0.0140 (0.0014) C14' * 0.0048 (0.0014) C15' * -0.0082 (0.0014) C16' * -0.0043 (0.0016) C17' * -0.0002 (0.0015) C18' * -0.0089 (0.0014) C19' * -0.0003 (0.0013) O3' * 0.0060 (0.0013) C20' * -0.0029 (0.0012) N1'

Rms deviation of fitted atoms = 0.0069

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
S	0.70206 (2)	0.50456 (5)	1.03604 (3)	0.01728 (10)
O1	0.52373 (7)	0.30901 (11)	0.71581 (8)	0.0180 (2)
O2	0.28479 (6)	0.55263 (11)	0.29437 (8)	0.0211 (3)
O3	1.02907 (7)	0.86352 (16)	0.88836 (10)	0.0411 (4)
N1	0.70429 (8)	0.60538 (15)	0.82176 (11)	0.0181 (3)
H01	0.6823 (9)	0.6052 (17)	0.7547 (10)	0.021 (5)*
C2	0.66134 (9)	0.54043 (16)	0.90110 (11)	0.0125 (3)
N3	0.57906 (8)	0.50134 (15)	0.86822 (10)	0.0142 (3)
H03	0.5512 (8)	0.4637 (14)	0.9164 (10)	0.005 (4)*
N4	0.53669 (8)	0.53524 (14)	0.76180 (10)	0.0133 (3)
H04	0.5143 (10)	0.6113 (14)	0.7606 (14)	0.027 (6)*
C5	0.50445 (9)	0.42990 (16)	0.69256 (13)	0.0128 (3)
C6	0.44704 (9)	0.47015 (16)	0.58951 (12)	0.0122 (3)
C7	0.41778 (9)	0.36550 (16)	0.51243 (12)	0.0148 (4)
H7	0.4349	0.2724	0.5274	0.018*
C8	0.36421 (10)	0.39690 (17)	0.41495 (12)	0.0169 (4)
H8	0.3447	0.3252	0.3634	0.020*
C9	0.33859 (9)	0.53260 (17)	0.39175 (12)	0.0157 (3)
C10	0.36805 (10)	0.63793 (17)	0.46663 (12)	0.0171 (4)
H10	0.3516	0.7311	0.4507	0.021*
C11	0.42156 (10)	0.60574 (16)	0.56447 (13)	0.0157 (4)
H11	0.4413	0.6777	0.6156	0.019*
C12	0.25273 (10)	0.69102 (17)	0.27136 (13)	0.0244 (4)
H12A	0.3015	0.7539	0.2577	0.029*
H12B	0.2234	0.7264	0.3374	0.029*
C13	0.18893 (11)	0.68298 (19)	0.16578 (13)	0.0312 (5)
H13A	0.2177	0.6421	0.1025	0.047*
H13B	0.1685	0.7762	0.1443	0.047*
H13C	0.1391	0.6255	0.1821	0.047*
C14	0.78727 (10)	0.67202 (18)	0.84138 (13)	0.0198 (4)
C15	0.85155 (11)	0.6460 (2)	0.76923 (14)	0.0428 (6)
H15	0.8414	0.5821	0.7078	0.051*
C16	0.93107 (12)	0.7134 (3)	0.78670 (14)	0.0503 (7)
H16	0.9746	0.6970	0.7357	0.060*
C17	0.94779 (10)	0.8035 (2)	0.87684 (14)	0.0298 (5)
C18	0.88347 (10)	0.83019 (18)	0.94777 (15)	0.0270 (4)
H18	0.8938	0.8933	1.0097	0.032*
C19	0.80302 (10)	0.76466 (18)	0.92888 (15)	0.0272 (4)
H19	0.7584	0.7846	0.9775	0.033*
C20	1.04658 (11)	0.9572 (2)	0.98097 (15)	0.0376 (5)
H20A	1.0051	1.0342	0.9729	0.056*
H20B	1.1061	0.9930	0.9803	0.056*
H20C	1.0406	0.9092	1.0536	0.056*
S'	0.69682 (2)	0.51034 (4)	0.53698 (3)	0.01624 (9)
O1'	0.52337 (7)	0.30780 (11)	0.21440 (8)	0.0184 (2)
O2'	0.28670 (6)	0.54492 (11)	−0.21151 (8)	0.0215 (3)
O3'	1.04034 (7)	0.80274 (17)	0.38417 (11)	0.0439 (4)
N1'	0.70424 (8)	0.58667 (14)	0.31685 (11)	0.0161 (3)
H01'	0.6834 (9)	0.5828 (16)	0.2504 (10)	0.017 (5)*
C2'	0.65809 (9)	0.53631 (15)	0.39935 (11)	0.0122 (3)
N3'	0.57447 (7)	0.50178 (15)	0.36778 (10)	0.0139 (3)
H03'	0.5419 (8)	0.4738 (15)	0.4176 (10)	0.012 (4)*
N4'	0.53359 (8)	0.53414 (14)	0.26033 (10)	0.0133 (3)
H04'	0.5104 (10)	0.6123 (14)	0.2551 (13)	0.023 (5)*
C5'	0.50319 (9)	0.42750 (16)	0.19115 (12)	0.0130 (3)
C6'	0.44667 (9)	0.46655 (16)	0.08647 (12)	0.0118 (3)
C7'	0.42218 (9)	0.36192 (16)	0.00689 (12)	0.0140 (3)
H7'	0.4418	0.2699	0.0212	0.017*
C8'	0.36966 (9)	0.39163 (17)	−0.09224 (12)	0.0152 (3)
H8'	0.3539	0.3203	−0.1460	0.018*
C9'	0.33984 (9)	0.52599 (17)	−0.11327 (12)	0.0157 (3)
C10'	0.36423 (10)	0.63083 (17)	−0.03574 (13)	0.0173 (4)
H10'	0.3450	0.7229	−0.0508	0.021*
C11'	0.41673 (10)	0.60055 (16)	0.06368 (13)	0.0155 (4)
H11'	0.4325	0.6723	0.1170	0.019*
C12'	0.25161 (11)	0.68144 (18)	−0.23382 (14)	0.0274 (4)
H12C	0.2990	0.7471	−0.2472	0.033*
H12D	0.2217	0.7144	−0.1675	0.033*
C13'	0.18795 (12)	0.6718 (2)	−0.33901 (14)	0.0392 (5)
H13D	0.2167	0.6298	−0.4019	0.059*
H13E	0.1676	0.7647	−0.3616	0.059*
H13F	0.1381	0.6147	−0.3220	0.059*
C14'	0.79061 (10)	0.64214 (18)	0.33595 (13)	0.0187 (4)
C15'	0.85761 (10)	0.5858 (2)	0.28031 (13)	0.0280 (4)
H15'	0.8472	0.5088	0.2305	0.034*
C16'	0.94058 (10)	0.6430 (2)	0.29804 (13)	0.0350 (5)
H16'	0.9869	0.6051	0.2597	0.042*
C17'	0.95622 (10)	0.7544 (2)	0.37088 (14)	0.0294 (5)
C18'	0.88890 (10)	0.81103 (19)	0.42619 (15)	0.0282 (4)
H18'	0.8994	0.8873	0.4767	0.034*
C19'	0.80553 (10)	0.75494 (18)	0.40688 (14)	0.0259 (4)
H19'	0.7586	0.7948	0.4429	0.031*
C20'	1.05700 (12)	0.9175 (2)	0.45930 (16)	0.0441 (6)
H20D	1.0241	0.9980	0.4285	0.066*
H20E	1.1194	0.9387	0.4658	0.066*
H20F	1.0389	0.8946	0.5352	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0191 (2)	0.0208 (3)	0.01124 (19)	−0.0005 (2)	−0.00234 (16)	0.00053 (18)
O1	0.0241 (6)	0.0118 (6)	0.0177 (6)	0.0013 (5)	−0.0002 (5)	0.0031 (5)
O2	0.0243 (6)	0.0218 (7)	0.0157 (6)	0.0006 (5)	−0.0066 (5)	0.0002 (5)
O3	0.0235 (7)	0.0669 (11)	0.0330 (7)	−0.0240 (7)	0.0037 (6)	−0.0058 (7)
N1	0.0150 (7)	0.0272 (9)	0.0117 (7)	−0.0055 (6)	−0.0012 (6)	0.0051 (6)
C2	0.0115 (7)	0.0120 (9)	0.0140 (8)	0.0012 (6)	0.0010 (6)	−0.0018 (6)
N3	0.0154 (6)	0.0180 (8)	0.0092 (7)	−0.0034 (6)	0.0009 (5)	0.0031 (6)
N4	0.0148 (7)	0.0116 (8)	0.0127 (7)	0.0000 (6)	−0.0026 (5)	0.0001 (6)
C5	0.0123 (8)	0.0125 (9)	0.0143 (8)	−0.0011 (7)	0.0043 (6)	0.0009 (7)
C6	0.0129 (8)	0.0110 (9)	0.0131 (8)	−0.0026 (6)	0.0023 (6)	−0.0001 (6)
C7	0.0164 (8)	0.0111 (9)	0.0172 (9)	−0.0009 (7)	0.0039 (7)	0.0010 (7)
C8	0.0177 (8)	0.0182 (10)	0.0144 (8)	−0.0043 (7)	−0.0002 (7)	−0.0049 (7)
C9	0.0121 (7)	0.0210 (10)	0.0138 (8)	−0.0019 (7)	0.0004 (6)	0.0034 (7)
C10	0.0221 (8)	0.0117 (9)	0.0170 (9)	0.0005 (7)	−0.0009 (7)	−0.0008 (7)
C11	0.0174 (8)	0.0131 (10)	0.0161 (9)	−0.0017 (7)	−0.0016 (7)	−0.0051 (7)
C12	0.0244 (10)	0.0245 (11)	0.0233 (10)	0.0044 (8)	−0.0041 (8)	0.0023 (8)
C13	0.0273 (10)	0.0399 (12)	0.0246 (10)	0.0040 (8)	−0.0076 (8)	0.0047 (8)
C14	0.0119 (8)	0.0278 (10)	0.0194 (9)	−0.0038 (7)	−0.0005 (6)	0.0082 (7)
C15	0.0288 (10)	0.0805 (18)	0.0202 (9)	−0.0255 (11)	0.0082 (7)	−0.0192 (10)
C16	0.0298 (11)	0.096 (2)	0.0274 (10)	−0.0292 (11)	0.0170 (8)	−0.0178 (11)
C17	0.0194 (9)	0.0454 (13)	0.0240 (9)	−0.0128 (8)	−0.0023 (7)	0.0086 (8)
C18	0.0211 (9)	0.0215 (10)	0.0387 (10)	−0.0053 (7)	0.0048 (8)	−0.0080 (8)
C19	0.0180 (9)	0.0214 (10)	0.0434 (10)	−0.0038 (7)	0.0087 (8)	−0.0077 (8)
C20	0.0245 (9)	0.0496 (13)	0.0374 (10)	−0.0197 (9)	−0.0049 (8)	0.0030 (9)
S'	0.0178 (2)	0.0181 (2)	0.01218 (19)	0.0001 (2)	−0.00225 (15)	−0.00011 (18)
O1'	0.0255 (6)	0.0116 (7)	0.0178 (6)	0.0013 (5)	−0.0007 (5)	0.0025 (5)
O2'	0.0246 (6)	0.0232 (7)	0.0151 (6)	−0.0011 (5)	−0.0079 (5)	−0.0006 (5)
O3'	0.0182 (6)	0.0690 (11)	0.0448 (8)	−0.0180 (7)	0.0041 (6)	−0.0062 (7)
N1'	0.0131 (7)	0.0236 (8)	0.0113 (7)	−0.0032 (6)	−0.0004 (6)	0.0006 (6)
C2'	0.0149 (8)	0.0081 (9)	0.0139 (8)	0.0017 (6)	0.0026 (6)	−0.0011 (6)
N3'	0.0121 (6)	0.0188 (8)	0.0105 (7)	−0.0020 (6)	−0.0004 (5)	0.0015 (6)
N4'	0.0139 (7)	0.0130 (9)	0.0124 (7)	0.0014 (6)	−0.0019 (5)	0.0020 (6)
C5'	0.0128 (8)	0.0138 (9)	0.0131 (8)	−0.0018 (7)	0.0042 (6)	0.0003 (7)
C6'	0.0096 (7)	0.0125 (9)	0.0134 (8)	−0.0018 (6)	0.0019 (6)	0.0016 (7)
C7'	0.0154 (8)	0.0114 (9)	0.0156 (8)	−0.0026 (7)	0.0037 (7)	−0.0018 (7)
C8'	0.0155 (8)	0.0156 (9)	0.0148 (8)	−0.0047 (7)	0.0031 (6)	−0.0026 (7)
C9'	0.0130 (7)	0.0238 (10)	0.0103 (7)	−0.0012 (7)	0.0006 (6)	0.0009 (7)
C10'	0.0180 (8)	0.0158 (9)	0.0178 (9)	0.0039 (7)	−0.0008 (7)	0.0037 (7)
C11'	0.0185 (8)	0.0131 (9)	0.0149 (9)	−0.0012 (7)	0.0008 (7)	−0.0017 (7)
C12'	0.0286 (10)	0.0264 (11)	0.0255 (10)	0.0024 (8)	−0.0079 (8)	0.0030 (8)
C13'	0.0399 (12)	0.0448 (14)	0.0299 (11)	0.0070 (10)	−0.0142 (9)	0.0026 (9)
C14'	0.0142 (8)	0.0253 (10)	0.0165 (8)	−0.0027 (7)	0.0009 (6)	0.0047 (7)
C15'	0.0187 (8)	0.0423 (12)	0.0233 (9)	−0.0025 (8)	0.0040 (7)	−0.0088 (8)
C16'	0.0164 (9)	0.0614 (14)	0.0277 (10)	−0.0018 (9)	0.0056 (7)	−0.0101 (9)
C17'	0.0150 (8)	0.0459 (13)	0.0266 (9)	−0.0101 (8)	−0.0013 (7)	0.0057 (9)
C18'	0.0212 (9)	0.0248 (10)	0.0384 (10)	−0.0065 (8)	0.0009 (8)	−0.0009 (8)
C19'	0.0145 (8)	0.0262 (11)	0.0377 (10)	−0.0007 (7)	0.0060 (7)	−0.0030 (8)
C20'	0.0260 (10)	0.0522 (14)	0.0521 (13)	−0.0214 (10)	−0.0083 (9)	0.0102 (10)

Geometric parameters (Å, º) top

S—C2	1.6823 (14)	C14'—C19'	1.378 (2)
O1—C5	1.2307 (17)	C14'—C15'	1.380 (2)
O2—C9	1.3618 (16)	C15'—C16'	1.391 (2)
O2—C12	1.4436 (18)	C16'—C17'	1.382 (2)
O3—C17	1.3757 (18)	C17'—C18'	1.383 (2)
O3—C20	1.420 (2)	C18'—C19'	1.394 (2)
N1—C2	1.3428 (18)	N1—H01	0.826 (11)
N1—C14	1.4316 (19)	N3—H03	0.822 (10)
C2—N3	1.3457 (17)	N4—H04	0.812 (12)
N3—N4	1.3926 (16)	C7—H7	0.9500
N4—C5	1.3672 (19)	C8—H8	0.9500
C5—C6	1.482 (2)	C10—H10	0.9500
C6—C11	1.393 (2)	C11—H11	0.9500
C6—C7	1.4030 (19)	C12—H12A	0.9900
C7—C8	1.3809 (19)	C12—H12B	0.9900
C8—C9	1.390 (2)	C13—H13A	0.9800
C9—C10	1.393 (2)	C13—H13B	0.9800
C10—C11	1.3853 (19)	C13—H13C	0.9800
C12—C13	1.5108 (19)	C15—H15	0.9500
C14—C19	1.366 (2)	C16—H16	0.9500
C14—C15	1.380 (2)	C18—H18	0.9500
C15—C16	1.387 (2)	C19—H19	0.9500
C16—C17	1.375 (3)	C20—H20A	0.9800
C17—C18	1.372 (2)	C20—H20B	0.9800
C18—C19	1.392 (2)	C20—H20C	0.9800
S'—C2'	1.6856 (14)	N1'—H01'	0.816 (11)
O1'—C5'	1.2229 (17)	N3'—H03'	0.847 (10)
O2'—C9'	1.3630 (16)	N4'—H04'	0.836 (12)
O2'—C12'	1.4417 (19)	C7'—H7'	0.9500
O3'—C17'	1.3733 (18)	C8'—H8'	0.9500
O3'—C20'	1.425 (2)	C10'—H10'	0.9500
N1'—C2'	1.3402 (17)	C11'—H11'	0.9500
N1'—C14'	1.4335 (19)	C12'—H12C	0.9900
C2'—N3'	1.3501 (17)	C12'—H12D	0.9900
N3'—N4'	1.3908 (16)	C13'—H13D	0.9800
N4'—C5'	1.3678 (19)	C13'—H13E	0.9800
C5'—C6'	1.487 (2)	C13'—H13F	0.9800
C6'—C11'	1.393 (2)	C15'—H15'	0.9500
C6'—C7'	1.4039 (19)	C16'—H16'	0.9500
C7'—C8'	1.3840 (19)	C18'—H18'	0.9500
C8'—C9'	1.393 (2)	C19'—H19'	0.9500
C9'—C10'	1.390 (2)	C20'—H20D	0.9800
C10'—C11'	1.3877 (19)	C20'—H20E	0.9800
C12'—C13'	1.507 (2)	C20'—H20F	0.9800

C9—O2—C12	117.42 (12)	C6—C7—H7	119.8
C17—O3—C20	116.97 (14)	C7—C8—H8	119.8
C2—N1—C14	125.98 (13)	C9—C8—H8	119.8
N1—C2—N3	116.31 (13)	C11—C10—H10	120.3
N1—C2—S	125.42 (11)	C9—C10—H10	120.3
N3—C2—S	118.27 (11)	C10—C11—H11	119.3
C2—N3—N4	122.97 (12)	C6—C11—H11	119.3
C5—N4—N3	118.10 (13)	O2—C12—H12A	110.3
O1—C5—N4	120.60 (15)	C13—C12—H12A	110.3
O1—C5—C6	122.96 (14)	O2—C12—H12B	110.3
N4—C5—C6	116.44 (14)	C13—C12—H12B	110.3
C11—C6—C7	118.40 (14)	H12A—C12—H12B	108.6
C11—C6—C5	123.71 (13)	C12—C13—H13A	109.5
C7—C6—C5	117.89 (14)	C12—C13—H13B	109.5
C8—C7—C6	120.43 (15)	H13A—C13—H13B	109.5
C7—C8—C9	120.49 (15)	C12—C13—H13C	109.5
O2—C9—C8	116.02 (14)	H13A—C13—H13C	109.5
O2—C9—C10	124.21 (15)	H13B—C13—H13C	109.5
C8—C9—C10	119.77 (14)	C14—C15—H15	120.1
C11—C10—C9	119.48 (15)	C16—C15—H15	120.1
C10—C11—C6	121.42 (14)	C17—C16—H16	119.5
O2—C12—C13	106.96 (13)	C15—C16—H16	119.5
C19—C14—C15	119.26 (15)	C17—C18—H18	120.0
C19—C14—N1	120.81 (15)	C19—C18—H18	120.0
C15—C14—N1	119.90 (15)	C14—C19—H19	119.5
C14—C15—C16	119.76 (17)	C18—C19—H19	119.5
C17—C16—C15	120.94 (17)	O3—C20—H20A	109.5
C18—C17—C16	119.13 (16)	O3—C20—H20B	109.5
C18—C17—O3	124.15 (16)	H20A—C20—H20B	109.5
C16—C17—O3	116.71 (16)	O3—C20—H20C	109.5
C17—C18—C19	119.93 (16)	H20A—C20—H20C	109.5
C14—C19—C18	120.94 (16)	H20B—C20—H20C	109.5
C9'—O2'—C12'	117.59 (12)	C2'—N1'—H01'	118.7 (11)
C17'—O3'—C20'	116.84 (14)	C14'—N1'—H01'	116.6 (11)
C2'—N1'—C14'	124.62 (13)	C2'—N3'—H03'	120.0 (9)
N1'—C2'—N3'	116.56 (13)	N4'—N3'—H03'	116.5 (9)
N1'—C2'—S'	125.22 (11)	C5'—N4'—H04'	121.1 (11)
N3'—C2'—S'	118.21 (11)	N3'—N4'—H04'	115.2 (11)
C2'—N3'—N4'	122.41 (12)	C8'—C7'—H7'	119.7
C5'—N4'—N3'	117.96 (13)	C6'—C7'—H7'	119.7
O1'—C5'—N4'	121.01 (15)	C7'—C8'—H8'	120.0
O1'—C5'—C6'	122.84 (14)	C9'—C8'—H8'	120.0
N4'—C5'—C6'	116.14 (14)	C11'—C10'—H10'	120.1
C11'—C6'—C7'	118.59 (14)	C9'—C10'—H10'	120.1
C11'—C6'—C5'	123.61 (14)	C10'—C11'—H11'	119.5
C7'—C6'—C5'	117.80 (14)	C6'—C11'—H11'	119.5
C8'—C7'—C6'	120.58 (15)	O2'—C12'—H12C	110.3
C7'—C8'—C9'	120.05 (14)	C13'—C12'—H12C	110.3
O2'—C9'—C10'	124.03 (15)	O2'—C12'—H12D	110.3
O2'—C9'—C8'	115.99 (14)	C13'—C12'—H12D	110.3
C10'—C9'—C8'	119.97 (14)	H12C—C12'—H12D	108.5
C11'—C10'—C9'	119.79 (15)	C12'—C13'—H13D	109.5
C10'—C11'—C6'	121.00 (15)	C12'—C13'—H13E	109.5
O2'—C12'—C13'	107.32 (14)	H13D—C13'—H13E	109.5
C19'—C14'—C15'	120.33 (15)	C12'—C13'—H13F	109.5
C19'—C14'—N1'	119.55 (15)	H13D—C13'—H13F	109.5
C15'—C14'—N1'	120.08 (15)	H13E—C13'—H13F	109.5
C14'—C15'—C16'	119.21 (17)	C14'—C15'—H15'	120.4
C17'—C16'—C15'	120.65 (16)	C16'—C15'—H15'	120.4
O3'—C17'—C16'	116.52 (16)	C17'—C16'—H16'	119.7
O3'—C17'—C18'	123.46 (17)	C15'—C16'—H16'	119.7
C16'—C17'—C18'	120.02 (16)	C17'—C18'—H18'	120.4
C17'—C18'—C19'	119.23 (17)	C19'—C18'—H18'	120.4
C14'—C19'—C18'	120.52 (16)	C14'—C19'—H19'	119.7
C2—N1—H01	118.0 (11)	C18'—C19'—H19'	119.7
C14—N1—H01	116.0 (11)	O3'—C20'—H20D	109.5
C2—N3—H03	117.6 (9)	O3'—C20'—H20E	109.5
N4—N3—H03	119.0 (9)	H20D—C20'—H20E	109.5
C5—N4—H04	122.2 (12)	O3'—C20'—H20F	109.5
N3—N4—H04	113.2 (12)	H20D—C20'—H20F	109.5
C8—C7—H7	119.8	H20E—C20'—H20F	109.5

C14—N1—C2—N3	171.14 (15)	C14'—N1'—C2'—N3'	173.21 (15)
C14—N1—C2—S	−9.0 (2)	C14'—N1'—C2'—S'	−8.1 (2)
N1—C2—N3—N4	−5.3 (2)	N1'—C2'—N3'—N4'	−9.0 (2)
S—C2—N3—N4	174.82 (11)	S'—C2'—N3'—N4'	172.22 (11)
C2—N3—N4—C5	123.25 (16)	C2'—N3'—N4'—C5'	119.34 (16)
N3—N4—C5—O1	−10.8 (2)	N3'—N4'—C5'—O1'	−11.7 (2)
N3—N4—C5—C6	169.88 (12)	N3'—N4'—C5'—C6'	169.66 (11)
O1—C5—C6—C11	177.14 (15)	O1'—C5'—C6'—C11'	174.11 (15)
N4—C5—C6—C11	−3.6 (2)	N4'—C5'—C6'—C11'	−7.2 (2)
O1—C5—C6—C7	−3.6 (2)	O1'—C5'—C6'—C7'	−5.6 (2)
N4—C5—C6—C7	175.64 (13)	N4'—C5'—C6'—C7'	173.03 (13)
C11—C6—C7—C8	−0.7 (2)	C11'—C6'—C7'—C8'	0.2 (2)
C5—C6—C7—C8	−179.97 (13)	C5'—C6'—C7'—C8'	180.00 (13)
C6—C7—C8—C9	0.1 (2)	C6'—C7'—C8'—C9'	−0.7 (2)
C12—O2—C9—C8	176.35 (13)	C12'—O2'—C9'—C10'	−2.1 (2)
C12—O2—C9—C10	−3.6 (2)	C12'—O2'—C9'—C8'	177.49 (13)
C7—C8—C9—O2	−179.13 (12)	C7'—C8'—C9'—O2'	−178.38 (12)
C7—C8—C9—C10	0.8 (2)	C7'—C8'—C9'—C10'	1.2 (2)
O2—C9—C10—C11	178.93 (13)	O2'—C9'—C10'—C11'	178.20 (13)
C8—C9—C10—C11	−1.0 (2)	C8'—C9'—C10'—C11'	−1.4 (2)
C9—C10—C11—C6	0.4 (2)	C9'—C10'—C11'—C6'	1.0 (2)
C7—C6—C11—C10	0.5 (2)	C7'—C6'—C11'—C10'	−0.4 (2)
C5—C6—C11—C10	179.72 (13)	C5'—C6'—C11'—C10'	179.86 (13)
C9—O2—C12—C13	−174.97 (12)	C9'—O2'—C12'—C13'	−173.82 (13)
C2—N1—C14—C19	−50.0 (2)	C2'—N1'—C14'—C19'	−60.2 (2)
C2—N1—C14—C15	131.93 (18)	C2'—N1'—C14'—C15'	122.06 (18)
C19—C14—C15—C16	0.3 (3)	C19'—C14'—C15'—C16'	0.9 (3)
N1—C14—C15—C16	178.35 (18)	N1'—C14'—C15'—C16'	178.60 (16)
C14—C15—C16—C17	1.6 (3)	C14'—C15'—C16'—C17'	0.4 (3)
C15—C16—C17—C18	−2.2 (3)	C20'—O3'—C17'—C16'	−179.90 (16)
C15—C16—C17—O3	178.87 (19)	C20'—O3'—C17'—C18'	−0.1 (3)
C20—O3—C17—C18	0.9 (3)	C15'—C16'—C17'—O3'	179.18 (16)
C20—O3—C17—C16	179.71 (18)	C15'—C16'—C17'—C18'	−0.6 (3)
C16—C17—C18—C19	0.9 (3)	O3'—C17'—C18'—C19'	179.81 (17)
O3—C17—C18—C19	179.73 (17)	C16'—C17'—C18'—C19'	−0.4 (3)
C15—C14—C19—C18	−1.6 (3)	C15'—C14'—C19'—C18'	−2.0 (3)
N1—C14—C19—C18	−179.64 (16)	N1'—C14'—C19'—C18'	−179.66 (15)
C17—C18—C19—C14	1.0 (3)	C17'—C18'—C19'—C14'	1.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H01···S′	0.83 (1)	2.74 (1)	3.4483 (14)	146 (1)
N4—H04···O1′ⁱ	0.81 (1)	2.02 (1)	2.8156 (17)	168 (2)
N1′—H01′···Sⁱⁱ	0.82 (1)	2.66 (1)	3.3772 (14)	148 (1)
N4′—H04′···O1ⁱ	0.84 (1)	2.01 (1)	2.8228 (18)	164 (2)
C11′—H11′···O1ⁱ	0.95	2.41	3.3378 (19)	166
C11—H11···O1′ⁱ	0.95	2.38	3.2927 (18)	162
C20—H20B···Sⁱⁱⁱ	0.98	2.98	3.9215 (17)	161
C20′—H20E···S′^iv	0.98	2.92	3.8936 (18)	175
C10′—H10′···Sⁱ	0.95	2.83	3.7559 (17)	166
C10—H10···S′ⁱ	0.95	2.81	3.7369 (17)	166
C15′—H15′···Sⁱⁱ	0.95	3.05	3.6482 (16)	123
C15—H15···S′	0.95	2.94	3.6925 (17)	137
N3′—H03′···Cg	0.85 (1)	2.53	3.25	144
N3—H03···Cg'^v	0.82 (1)	2.65	3.29	135

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₉N₃O₃S
M_r	345.41
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	15.40429 (13), 9.67120 (9), 11.69922 (9)
β (°)	95.0922 (7)
V (Å³)	1736.05 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.3 × 0.2 × 0.1

Data collection
Diffractometer	Oxford Diffraction Xcalibur E
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.981, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	44704, 9918, 6348
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.714

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.055, 0.96
No. of reflections	9918
No. of parameters	461
No. of restraints	16
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.23
Absolute structure	Flack (1983), 4562 Friedel pairs
Absolute structure parameter	0.01 (3)

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Siemens, 1994).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H01···S'	0.826 (11)	2.735 (12)	3.4483 (14)	145.5 (14)
N4—H04···O1'ⁱ	0.812 (12)	2.016 (13)	2.8156 (17)	168.2 (17)
N1'—H01'···Sⁱⁱ	0.816 (11)	2.659 (12)	3.3772 (14)	147.8 (14)
N4'—H04'···O1ⁱ	0.836 (12)	2.011 (13)	2.8228 (18)	163.7 (15)
C11'—H11'···O1ⁱ	0.95	2.41	3.3378 (19)	166.3
C11—H11···O1'ⁱ	0.95	2.38	3.2927 (18)	162.2
C20—H20B···Sⁱⁱⁱ	0.98	2.98	3.9215 (17)	161.3
C20'—H20E···S'^iv	0.98	2.92	3.8936 (18)	174.6
C10'—H10'···Sⁱ	0.95	2.83	3.7559 (17)	165.7
C10—H10···S'ⁱ	0.95	2.81	3.7369 (17)	165.8
C15'—H15'···Sⁱⁱ	0.95	3.05	3.6482 (16)	122.8
C15—H15···S'	0.95	2.94	3.6925 (17)	137.1
N3'—H03'···Cg	0.847 (10)	2.53	3.25	144
N3—H03···Cg'^v	0.822 (10)	2.65	3.29	135

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

References

Al-Masoudi, I. A., Al-Soud, Y. A., Al-Salihi, N. J. & Al-Masoudi, N. A. (2006). Chem. Heterocycl. Comp. 42, 1377–1403. CrossRef CAS Google Scholar
Angelusiu, M. V., Almajan, G. L., Rosu, T., Negoiu, M., Almajan, E. R. & Roy, J. (2009). Eur. J. Med. Chem. 44, 3323–3329. Web of Science CrossRef PubMed CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Ghosh, S., Mishra, A. K. & Bhatia, G. (2009). Bioorg. Med. Chem. Lett. 19, 386–389. Web of Science CrossRef PubMed CAS Google Scholar
Kucukguzel, S. G., Kucukguzel, I., Tatar, E. & Rollas, S. (2007). Eur. J. Med. Chem. 42, 893–901. Web of Science CrossRef PubMed Google Scholar
Liu, J., Cao, R., Yi, W., Ma, C., Wan, Y., Zhou, B., Ma, L. & Song, H. (2009). Eur. J. Med. Chem. 44, 1773–1778. Web of Science CrossRef PubMed CAS Google Scholar
Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction Ltd., Yarnton, Oxford, UK. Google Scholar
Serwar, M., Akhtar, T., Hameed, S. & Khan, K. M. (2009). ARKIVOC pp. 210–221. Google Scholar
Serwer, M., Khawar Rauf, M., Ebihara, M. & Hameed, S. (2008). Acta Cryst. E64, o812. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1994). XP. Siemens Analytical X-ray Instruments, Madison, USA. Google Scholar
Tomascikava, J., Imrich, J. & Danihel, I. (2008). Molecules 13, 501–518. Web of Science PubMed Google Scholar
Tozkoparan, B., Kupeli, E., Yesilada, E. & Ertan, M. (2007). Bioorg. Med. Chem. 15, 1808–1814. Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 11| November 2009| Pages o2604-o2605

https://doi.org/10.1107/S1600536809036599

Open

access