N-Methyl-4-(4-pivalamido­phenyl­sulfan­yl)picolinamide hemihydrate

Ye, T.-H.; Huang, T.-T.; Shi, Y.-J.; Xiong, Y.; Yu, L.-T.

doi:10.1107/S1600536811012268

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1098

doi:10.1107/S1600536811012268

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N-Methyl-4-(4-pivalamidophenylsulfanyl)picolinamide hemihydrate

Ting-Hong Ye,^a Ting-Ting Huang,^a Yao-Jie Shi,^a Ying Xiong ^b and Luo-Ting Yu ^a ^*

^aState Key Laboratory of Biotherapy and Cancer Center, West China Hospital, West China Medical School, Sichuan University, Chengdu 610041, People's Republic of China, and ^bWest China School of Pharmacy, Sichuan University, Chengdu 610041, People's Republic of China
^*Correspondence e-mail: yuluot@scu.edu.cn

(Received 22 February 2011; accepted 2 April 2011; online 13 April 2011)

In the title compound, C₁₈H₂₁N₃O₂S·0.5H₂O, the benzene ring makes dihedral angles of 88.59 (6) and 40.74 (8)° with the pyridine ring and the amide group, respectively. The water O atom lies on a twofold axis. In the crystal, the organic molecules and the water molecules are linked via O—H⋯O hydrogen bonds, while the organic molecules are connected to each other via N—H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For related compounds and their biological activity, see: Khire et al. (2004 ); Dominguez et al. (2007 ).

Experimental

Crystal data

C₁₈H₂₁N₃O₂S·0.5H₂O
M_r = 352.46
Monoclinic, C 2/c
a = 12.7413 (4) Å
b = 17.5056 (8) Å
c = 17.1978 (6) Å
β = 108.632 (4)°
V = 3634.8 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 293 K
0.24 × 0.22 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.966, T_max = 1.000
3714 measured reflections
3714 independent reflections
2498 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.111
S = 0.96
3714 reflections
238 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1ⁱ	0.854 (18)	2.335 (18)	3.0317 (19)	139.0 (15)
O3—H3⋯O2ⁱⁱ	0.87 (2)	1.94 (2)	2.8059 (18)	174.2
N1—H1⋯O3	0.850 (19)	2.269 (19)	3.089 (2)	162.3 (18)
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811012268/zq2092sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811012268/zq2092Isup2.hkl

checkCIF report

Comment top

Sorafenib is a molecule of great importance owing to its antitumor properties (Khire et al., 2004; Dominguez et al., 2007). The title compound, which is one of its derivatives, possesses even better in vitro anticancer activity against both two tumor cell lines (HCT116 and HEPG2). As a potent antitumor drug, we report here its crystal structure.

In the title molecule, C₁₈H₂₁N₃O₂S.0.5(H₂O), the central benzene ring makes dihedral angles of 88.59 (6)° and 40.74 (8)° with the pyridine and amide bonds, respectively (Fig. 1). The O atom of the isolated water molecule lies on a two-fold axis. In the crystal structure, two organic molecules and one water molecule are linked via the O3—H3···O2ⁱⁱ hydrogen bonds, while organic molecules are connected with each other via the N3—H3A···O1ⁱ hydrogen bonds, forming a three-dimensional network [symmetry codes: (i) x-1, y, z; (ii) x+3/2, y+3/2, z+1.Table 1 and Fig. 2].

Related literature top

For related compounds and their biological activity, see: Khire et al. (2004); Dominguez et al. (2007).

Experimental top

To the suspension of anhydrous potassium carbonate (0.69 g, 5.0 mmol) and 4-(4-aminophenylthio)-N-methylpicolinamide (0.52 g, 2.0 mmol) in 7.0 ml THF was added dropwise pivaloyl chloride (0.25 g, 2.1 mmol). After being stirred at room temperature for 2 h, the mixture was extracted with 30 ml EA and 30 ml brine for three times and the combined organic layers were dried over anhydrous sodium sulfate. Then the solution was concentrated under vacuum, and the residue was recrystallized from ethanol to give the title compound, with 40% yield. Crystals suitable for a X-ray analysis were obtained by slow evaporation from a solution of ethanol at room temperature.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A packing diagram of the title compound, with O–H···O and N–H···O hydrogen bonds shown as dotted red and blue lines, respectively.

4-{[4-(2,2-dimethylpropanamido)phenyl]sulfanyl}-N-methylpyridine- 2-carboxamide hemihydrate top

Crystal data top

C₁₈H₂₁N₃O₂S·0.5H₂O	F(000) = 1496
M_r = 352.46	D_x = 1.288 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -C 2yc	Cell parameters from 4009 reflections
a = 12.7413 (4) Å	θ = 3.2–28.9°
b = 17.5056 (8) Å	µ = 0.20 mm⁻¹
c = 17.1978 (6) Å	T = 293 K
β = 108.632 (4)°	Block, colourless
V = 3634.8 (2) Å³	0.24 × 0.22 × 0.18 mm
Z = 8

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	3714 independent reflections
Radiation source: fine-focus sealed tube	2498 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.000
Detector resolution: 16.0874 pixels mm^-1	θ_max = 26.4°, θ_min = 3.4°
ω scans	h = −15→15
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = 0→21
T_min = 0.966, T_max = 1.000	l = 0→21
3714 measured reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ²(F_o²) + (0.0661P)²] where P = (F_o² + 2F_c²)/3
3714 reflections	(Δ/σ)_max = 0.001
238 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₈H₂₁N₃O₂S·0.5H₂O	V = 3634.8 (2) Å³
M_r = 352.46	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 12.7413 (4) Å	µ = 0.20 mm⁻¹
b = 17.5056 (8) Å	T = 293 K
c = 17.1978 (6) Å	0.24 × 0.22 × 0.18 mm
β = 108.632 (4)°

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	3714 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	2498 reflections with I > 2σ(I)
T_min = 0.966, T_max = 1.000	R_int = 0.000
3714 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	Δρ_max = 0.25 e Å⁻³
3714 reflections	Δρ_min = −0.21 e Å⁻³
238 parameters

Special details top

Experimental. CrysAlisPro, Oxford Diffraction Ltd. (version 1.171.33.66). Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
S1	0.61494 (4)	0.59213 (4)	0.36246 (3)	0.0608 (2)
O1	1.13699 (9)	0.68403 (8)	0.59009 (7)	0.0587 (4)
O2	0.18072 (9)	0.62917 (8)	0.30133 (7)	0.0501 (3)
N1	1.04402 (11)	0.59473 (9)	0.63584 (9)	0.0426 (4)
N2	0.36966 (11)	0.62678 (10)	0.50293 (8)	0.0467 (4)
N3	0.15906 (11)	0.66751 (9)	0.42051 (9)	0.0437 (4)
C1	1.33721 (15)	0.64847 (17)	0.70547 (13)	0.0802 (8)
H1B	1.3331	0.6977	0.6800	0.120*
H1A	1.3476	0.6098	0.6690	0.120*
H1C	1.3984	0.6476	0.7556	0.120*
C2	1.23823 (17)	0.55645 (13)	0.76612 (13)	0.0702 (7)
H2C	1.3062	0.5537	0.8111	0.105*
H2A	1.2368	0.5165	0.7276	0.105*
H2B	1.1767	0.5505	0.7864	0.105*
C3	1.2132 (2)	0.69544 (16)	0.78024 (13)	0.0901 (8)
H3C	1.2060	0.7439	0.7528	0.135*
H3D	1.2756	0.6969	0.8296	0.135*
H3B	1.1471	0.6850	0.7938	0.135*
C4	1.23043 (13)	0.63306 (10)	0.72414 (10)	0.0412 (4)
C5	1.13433 (13)	0.63957 (11)	0.64372 (10)	0.0397 (4)
C6	0.94575 (12)	0.59550 (10)	0.56813 (10)	0.0382 (4)
C7	0.89869 (14)	0.66307 (11)	0.53038 (11)	0.0458 (4)
H7	0.9337	0.7095	0.5478	0.055*
C8	0.79980 (14)	0.66091 (12)	0.46693 (10)	0.0481 (5)
H8	0.7689	0.7062	0.4415	0.058*
C9	0.74604 (13)	0.59274 (12)	0.44062 (10)	0.0446 (5)
C10	0.79331 (13)	0.52514 (12)	0.47770 (10)	0.0479 (5)
H10	0.7582	0.4787	0.4601	0.058*
C11	0.89264 (13)	0.52707 (11)	0.54086 (10)	0.0444 (4)
H11	0.9243	0.4816	0.5654	0.053*
C12	0.52341 (13)	0.60419 (10)	0.41985 (10)	0.0399 (4)
C13	0.41182 (12)	0.61603 (10)	0.37742 (9)	0.0381 (4)
H13	0.3863	0.6161	0.3204	0.046*
C14	0.34005 (12)	0.62763 (10)	0.42101 (9)	0.0366 (4)
C15	0.47617 (14)	0.61313 (12)	0.54174 (11)	0.0559 (5)
H15	0.4987	0.6107	0.5987	0.067*
C16	0.55535 (14)	0.60244 (12)	0.50456 (10)	0.0507 (5)
H16	0.6289	0.5942	0.5356	0.061*
C17	0.21897 (12)	0.64171 (10)	0.37579 (10)	0.0382 (4)
C18	0.04265 (13)	0.68624 (11)	0.38587 (11)	0.0509 (5)
H18B	0.0278	0.7041	0.3306	0.076*
H18C	0.0240	0.7254	0.4183	0.076*
H18A	−0.0010	0.6415	0.3858	0.076*
H3A	0.1891 (14)	0.6747 (11)	0.4720 (11)	0.051 (5)*
H1	1.0476 (15)	0.5594 (11)	0.6705 (11)	0.056 (6)*
H3	0.9464 (16)	0.4381 (12)	0.7371 (14)	0.072 (7)*
O3	1.0000	0.47126 (12)	0.7500	0.0502 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0340 (2)	0.1137 (5)	0.0331 (2)	0.0111 (3)	0.00870 (18)	0.0027 (3)
O1	0.0487 (7)	0.0767 (10)	0.0474 (7)	−0.0134 (7)	0.0109 (6)	0.0197 (7)
O2	0.0346 (6)	0.0727 (9)	0.0386 (7)	−0.0011 (6)	0.0059 (5)	−0.0086 (6)
N1	0.0340 (7)	0.0498 (10)	0.0401 (8)	−0.0034 (7)	0.0061 (6)	0.0113 (8)
N2	0.0369 (7)	0.0677 (11)	0.0349 (8)	−0.0007 (7)	0.0106 (6)	−0.0011 (7)
N3	0.0350 (7)	0.0564 (10)	0.0389 (8)	0.0019 (7)	0.0107 (7)	−0.0019 (7)
C1	0.0398 (10)	0.134 (2)	0.0608 (13)	−0.0199 (12)	0.0076 (10)	0.0188 (14)
C2	0.0557 (11)	0.0722 (16)	0.0628 (13)	−0.0126 (11)	−0.0090 (10)	0.0177 (12)
C3	0.105 (2)	0.100 (2)	0.0551 (14)	0.0152 (16)	0.0122 (14)	−0.0235 (13)
C4	0.0380 (9)	0.0493 (11)	0.0338 (9)	−0.0092 (8)	0.0082 (7)	−0.0009 (8)
C5	0.0370 (9)	0.0459 (11)	0.0375 (9)	−0.0023 (8)	0.0139 (7)	0.0013 (8)
C6	0.0308 (8)	0.0478 (11)	0.0370 (9)	0.0005 (8)	0.0121 (7)	0.0052 (8)
C7	0.0409 (9)	0.0453 (11)	0.0507 (10)	0.0015 (8)	0.0138 (8)	0.0057 (9)
C8	0.0416 (9)	0.0563 (12)	0.0475 (10)	0.0138 (9)	0.0159 (8)	0.0157 (9)
C9	0.0300 (8)	0.0690 (13)	0.0352 (9)	0.0052 (9)	0.0108 (7)	0.0052 (9)
C10	0.0386 (9)	0.0567 (13)	0.0458 (10)	−0.0040 (9)	0.0098 (8)	−0.0017 (9)
C11	0.0368 (9)	0.0451 (11)	0.0471 (10)	0.0023 (8)	0.0073 (8)	0.0090 (8)
C12	0.0323 (8)	0.0511 (11)	0.0347 (9)	0.0008 (7)	0.0083 (7)	−0.0002 (8)
C13	0.0326 (8)	0.0485 (11)	0.0295 (8)	−0.0005 (7)	0.0048 (7)	−0.0007 (7)
C14	0.0323 (8)	0.0392 (10)	0.0351 (9)	−0.0035 (7)	0.0065 (7)	−0.0043 (8)
C15	0.0404 (9)	0.0945 (17)	0.0300 (9)	0.0005 (10)	0.0071 (7)	0.0001 (9)
C16	0.0340 (8)	0.0802 (15)	0.0331 (9)	0.0042 (9)	0.0042 (7)	0.0015 (9)
C17	0.0315 (8)	0.0397 (10)	0.0422 (10)	−0.0042 (7)	0.0102 (7)	−0.0014 (8)
C18	0.0380 (9)	0.0586 (13)	0.0585 (12)	0.0060 (9)	0.0189 (8)	0.0009 (10)
O3	0.0371 (10)	0.0505 (12)	0.0565 (11)	0.000	0.0056 (9)	0.000

Geometric parameters (Å, º) top

S1—C9	1.7783 (16)	C4—C5	1.531 (2)
S1—C12	1.7646 (17)	C6—C7	1.390 (2)
O1—C5	1.215 (2)	C6—C11	1.382 (2)
O2—C17	1.2355 (18)	C7—H7	0.9300
N1—C5	1.364 (2)	C7—C8	1.379 (2)
N1—C6	1.412 (2)	C8—H8	0.9300
N1—H1	0.850 (19)	C8—C9	1.378 (3)
N2—C14	1.337 (2)	C9—C10	1.387 (3)
N2—C15	1.329 (2)	C10—H10	0.9300
N3—C17	1.324 (2)	C10—C11	1.380 (2)
N3—C18	1.448 (2)	C11—H11	0.9300
N3—H3A	0.854 (18)	C12—C13	1.391 (2)
C1—H1B	0.9600	C12—C16	1.382 (2)
C1—H1A	0.9600	C13—H13	0.9300
C1—H1C	0.9600	C13—C14	1.370 (2)
C1—C4	1.519 (2)	C14—C17	1.510 (2)
C2—H2C	0.9600	C15—H15	0.9300
C2—H2A	0.9600	C15—C16	1.369 (2)
C2—H2B	0.9600	C16—H16	0.9300
C2—C4	1.511 (3)	C18—H18B	0.9600
C3—H3C	0.9600	C18—H18C	0.9600
C3—H3D	0.9600	C18—H18A	0.9600
C3—H3B	0.9600	O3—H3	0.87 (2)
C3—C4	1.519 (3)

O1—C5—N1	121.37 (15)	C6—N1—H1	114.8 (13)
O1—C5—C4	121.67 (15)	C6—C7—H7	120.2
O2—C17—N3	123.57 (14)	C6—C11—H11	119.5
O2—C17—C14	120.31 (14)	C7—C6—N1	122.01 (16)
N1—C5—C4	116.93 (14)	C7—C8—H8	119.5
N2—C14—C13	124.18 (14)	C8—C7—C6	119.68 (17)
N2—C14—C17	116.27 (14)	C8—C7—H7	120.2
N2—C15—H15	117.4	C8—C9—S1	120.11 (14)
N2—C15—C16	125.22 (16)	C8—C9—C10	119.37 (15)
N3—C17—C14	116.12 (14)	C9—C8—C7	121.07 (16)
N3—C18—H18B	109.5	C9—C8—H8	119.5
N3—C18—H18C	109.5	C9—C10—H10	120.2
N3—C18—H18A	109.5	C10—C9—S1	120.48 (15)
C1—C4—C3	109.12 (19)	C10—C11—C6	120.98 (16)
C1—C4—C5	107.93 (13)	C10—C11—H11	119.5
H1B—C1—H1A	109.5	C11—C6—N1	118.74 (15)
H1B—C1—H1C	109.5	C11—C6—C7	119.20 (15)
H1A—C1—H1C	109.5	C11—C10—C9	119.68 (17)
C2—C4—C1	109.39 (17)	C11—C10—H10	120.2
C2—C4—C3	109.59 (18)	C12—S1—C9	101.86 (7)
C2—C4—C5	114.16 (14)	C12—C13—H13	120.5
H2C—C2—H2A	109.5	C12—C16—H16	120.8
H2C—C2—H2B	109.5	C13—C12—S1	118.16 (12)
H2A—C2—H2B	109.5	C13—C14—C17	119.55 (14)
C3—C4—C5	106.51 (15)	C14—C13—C12	118.96 (14)
H3C—C3—H3D	109.5	C14—C13—H13	120.5
H3C—C3—H3B	109.5	C15—N2—C14	115.50 (14)
H3D—C3—H3B	109.5	C15—C16—C12	118.47 (15)
C4—C1—H1B	109.5	C15—C16—H16	120.8
C4—C1—H1A	109.5	C16—C12—S1	124.21 (12)
C4—C1—H1C	109.5	C16—C12—C13	117.62 (15)
C4—C2—H2C	109.5	C16—C15—H15	117.4
C4—C2—H2A	109.5	C17—N3—C18	122.88 (15)
C4—C2—H2B	109.5	C17—N3—H3A	120.1 (12)
C4—C3—H3C	109.5	C18—N3—H3A	117.0 (12)
C4—C3—H3D	109.5	H18B—C18—H18C	109.5
C4—C3—H3B	109.5	H18B—C18—H18A	109.5
C5—N1—C6	125.06 (15)	H18C—C18—H18A	109.5
C5—N1—H1	119.7 (13)

S1—C9—C10—C11	−176.99 (13)	C7—C8—C9—S1	176.56 (13)
S1—C12—C13—C14	−178.20 (13)	C7—C8—C9—C10	−1.1 (3)
S1—C12—C16—C15	179.54 (16)	C8—C9—C10—C11	0.7 (3)
N1—C6—C7—C8	−176.92 (15)	C9—S1—C12—C13	172.12 (14)
N1—C6—C11—C10	176.57 (15)	C9—S1—C12—C16	−8.07 (19)
N2—C14—C17—O2	−166.19 (16)	C9—C10—C11—C6	0.3 (3)
N2—C14—C17—N3	13.7 (2)	C11—C6—C7—C8	0.4 (3)
N2—C15—C16—C12	−1.4 (3)	C12—S1—C9—C8	−87.13 (15)
C1—C4—C5—O1	−32.9 (2)	C12—S1—C9—C10	90.55 (15)
C1—C4—C5—N1	148.93 (18)	C12—C13—C14—N2	−1.5 (3)
C2—C4—C5—O1	−154.74 (18)	C12—C13—C14—C17	179.11 (15)
C2—C4—C5—N1	27.1 (2)	C13—C12—C16—C15	−0.6 (3)
C3—C4—C5—O1	84.2 (2)	C13—C14—C17—O2	13.2 (2)
C3—C4—C5—N1	−94.0 (2)	C13—C14—C17—N3	−166.83 (16)
C5—N1—C6—C7	−41.0 (2)	C14—N2—C15—C16	1.9 (3)
C5—N1—C6—C11	141.63 (17)	C15—N2—C14—C13	−0.4 (3)
C6—N1—C5—O1	−1.4 (3)	C15—N2—C14—C17	178.99 (17)
C6—N1—C5—C4	176.82 (15)	C16—C12—C13—C14	2.0 (2)
C6—C7—C8—C9	0.6 (3)	C18—N3—C17—O2	−2.2 (3)
C7—C6—C11—C10	−0.9 (3)	C18—N3—C17—C14	177.90 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1ⁱ	0.854 (18)	2.335 (18)	3.0317 (19)	139.0 (15)
O3—H3···O2ⁱⁱ	0.87 (2)	1.94 (2)	2.8059 (18)	174.2
N1—H1···O3	0.850 (19)	2.269 (19)	3.089 (2)	162.3 (18)

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

Experimental details

Crystal data
Chemical formula	C₁₈H₂₁N₃O₂S·0.5H₂O
M_r	352.46
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	12.7413 (4), 17.5056 (8), 17.1978 (6)
β (°)	108.632 (4)
V (Å³)	3634.8 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.24 × 0.22 × 0.18

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.966, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	3714, 3714, 2498
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.111, 0.96
No. of reflections	3714
No. of parameters	238
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.21

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2006), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1ⁱ	0.854 (18)	2.335 (18)	3.0317 (19)	139.0 (15)
O3—H3···O2ⁱⁱ	0.87 (2)	1.94 (2)	2.8059 (18)	174.2
N1—H1···O3	0.850 (19)	2.269 (19)	3.089 (2)	162.3 (18)

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

Acknowledgements

We thank the Analytical and Testing Center of Sichuan University for the X-ray measurements.

References

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