(E)-4-[4-(Diethyl­amino)­benzyl­idene­ammonio]­benzene­sulfonate

Ruanwas, P.; Chantrapromma, S.; Fun, H.-K.

doi:10.1107/S1600536812026402

organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Pages o2155-o2156

https://doi.org/10.1107/S1600536812026402

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(E)-4-[4-(Diethylamino)benzylideneammonio]benzenesulfonate

Pumsak Ruanwas,^a Suchada Chantrapromma ^b ^*‡ and Hoong-Kun Fun ^c §

^aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: suchada.c@psu.ac.th

(Received 3 June 2012; accepted 11 June 2012; online 20 June 2012)

The title compound, C₁₇H₂₀N₂O₃S, synthesised from sulfanilic acid and 4-diethylaminobenzaldehyde, crystallized out as a zwitterion with the central N atom protonated. The zwitterion exists in an E conformation with respect to the C=N double bond. The dihedral angle between the benzene rings is 37.57 (5)°. In the crystal, the zwitterions are linked into a tape along the a axis by N—H⋯O hydrogen bonds. The crystal structure is further stabilized by weak C—H⋯O interactions and π–π interactions with a centroid–centroid distance of 3.8541 (6) Å. An O⋯O [2.8498 (11) Å] short contact is present.

Related literature

For bond-length data, see: Allen et al. (1987 ). For related structures, see: Banu & Golzar Hossain (2006 ); Yeap et al. (2010 ). For background and applications to sulfanilic acids, see: Chanawanno et al. (2010 ); Hussain et al. (2009 ); Kim et al. (2011 ); King (1991 ); Taylor et al. (2006 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₇H₂₀N₂O₃S
M_r = 332.42
Triclinic, $[P \overline 1]$
a = 8.1227 (1) Å
b = 8.8745 (1) Å
c = 12.4070 (2) Å
α = 69.386 (1)°
β = 72.442 (1)°
γ = 75.509 (1)°
V = 787.63 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 100 K
0.45 × 0.22 × 0.14 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.906, T_max = 0.969
24759 measured reflections
5685 independent reflections
5040 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.097
S = 1.04
5685 reflections
214 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.77 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O3ⁱ	0.865 (18)	2.466 (17)	3.0309 (12)	123.6 (13)
N1—H1N1⋯O3ⁱⁱ	0.865 (18)	2.076 (18)	2.8989 (12)	158.7 (16)
C7—H7A⋯O2ⁱⁱⁱ	0.93	2.39	3.2719 (13)	157
C13—H13A⋯O3ⁱⁱ	0.93	2.40	3.3002 (13)	164
C14—H14A⋯O1^iv	0.97	2.58	3.4805 (14)	155
Symmetry codes: (i) x+1, y, z; (ii) -x, -y+1, -z+1; (iii) -x, -y, -z+1; (iv) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812026402/is5152sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812026402/is5152Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812026402/is5152Isup3.cml

checkCIF report

Comment top

Benzenesulfonic acid is a very strong acid and coupled with aromatic components are interesting chemical reagents (King, 1991). Many of these combinations exhibit pharmaceutical and biological activities (Chanawanno et al., 2010; Taylor et al., 2006) and were also used as whitening reagents (Hussain et al., 2009) and fluorescence sensors (Kim et al., 2011). The title compound (I) was synthesized on account of its fluorescence property. It was found that (I) shows solid state fluorescence with the maximum emission at 625 nm when was excited at 400 nm. Herein the synthesis and crystal structure of (I) are reported.

In Fig. 1, the molecule of (I), C₁₇H₂₀N₂O₃S, crystallized out as a zwitterion with the N1 atom protonated. The hydrogen is more preferably attached to the nitrogen atom due to the stronger basicity of NH₂ group compared to the SO₃^- substituent (Banu & Golzar Hossain, 2006; Yeap et al., 2010). The zwitterion exists in an E configuration with respect to the central C═N double bond [1.3146 (12)°] with the torsion angle C6–N1–C7–C8 being 172.99 (9)°. The molecule is twisted with the dihedral angle between the two benzene rings being 37.57 (5) °. The two ethyl groups of diethylamino are out of its bound benzene ring plane with the torsion angles of C11–N2–C14–C15 = 84.88 (12)° and C11–N2–C16–C17 = 86.61 (12)° and they are oriented in oppositional directions to each other (Fig. 1). The bond distances agree with the literature values (Allen et al., 1987) and are comparable with the related structure (Yeap et al., 2010).

In the crystal packing (Fig. 2), the zwitterions are linked by intermolecular N—H···O hydrogen bonds (Table 1) into tapes along the a axis. The crystal is stabilized by intermolecular N—H···O hydrogen bonds and weak C—H···O interactions (Table 1). A π–π interaction with the distance of Cg₁···Cg₁ⁱⁱ = 3.8541 (6) Å was observed; Cg₁ is the centroid of C1–C6 benzene ring. An O···O^v short contact [2.8498 (11) Å; symmetry code (v) = -1 - x, 1 - y, 1 - z] was presented.

Related literature top

For bond-length data, see: Allen et al. (1987). For related structures, see: Banu & Golzar Hossain (2006); Yeap et al. (2010). For background and applications to sulfanilic acids, see: Chanawanno et al. (2010); Hussain et al. (2009); Kim et al. (2011); King (1991); Taylor et al. (2006). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

Sulfanilic acid (0.5 g, 2.8 mmol) was dissolved in water (10 ml) and then 4-diethylaminobenzaldehyde (0.5 g, 2.8 mmol) was added. The mixture was refluxed at 120 °C for 2 h. The precipitate was filtered, washed with water and purified by recrystallization from ethanol to afford the compound I (yield 79%). Yellow block-shaped single crystals of the title compound suitable for X-ray structure determination were formed from recrystallization from ethanol by the slow evaporation of the solvent at room temperature after a week (m.p. 540–541 K).

Structure description top

For bond-length data, see: Allen et al. (1987). For related structures, see: Banu & Golzar Hossain (2006); Yeap et al. (2010). For background and applications to sulfanilic acids, see: Chanawanno et al. (2010); Hussain et al. (2009); Kim et al. (2011); King (1991); Taylor et al. (2006). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 60% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound viewed approximately along the b axis, showing the tape structures running along the a axis. Hydrogen bonds are shown as dashed lines.

(E)-4-[4-(Diethylamino)benzylideneammonio]benzenesulfonate top

Crystal data top

C₁₇H₂₀N₂O₃S	Z = 2
M_r = 332.42	F(000) = 352
Triclinic, P1	D_x = 1.402 Mg m⁻³
Hall symbol: -P 1	Melting point = 540–541 K
a = 8.1227 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.8745 (1) Å	Cell parameters from 5685 reflections
c = 12.4070 (2) Å	θ = 1.8–32.5°
α = 69.386 (1)°	µ = 0.22 mm⁻¹
β = 72.442 (1)°	T = 100 K
γ = 75.509 (1)°	Block, yellow
V = 787.63 (2) Å³	0.45 × 0.22 × 0.14 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	5685 independent reflections
Radiation source: sealed tube	5040 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
φ and ω scans	θ_max = 32.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
T_min = 0.906, T_max = 0.969	k = −13→13
24759 measured reflections	l = −18→17

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0477P)² + 0.3239P] where P = (F_o² + 2F_c²)/3
5685 reflections	(Δ/σ)_max = 0.001
214 parameters	Δρ_max = 0.77 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₇H₂₀N₂O₃S	γ = 75.509 (1)°
M_r = 332.42	V = 787.63 (2) Å³
Triclinic, P1	Z = 2
a = 8.1227 (1) Å	Mo Kα radiation
b = 8.8745 (1) Å	µ = 0.22 mm⁻¹
c = 12.4070 (2) Å	T = 100 K
α = 69.386 (1)°	0.45 × 0.22 × 0.14 mm
β = 72.442 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	5685 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	5040 reflections with I > 2σ(I)
T_min = 0.906, T_max = 0.969	R_int = 0.024
24759 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.77 e Å⁻³
5685 reflections	Δρ_min = −0.40 e Å⁻³
214 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1) K.

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	−0.35313 (3)	0.23999 (3)	0.67776 (2)	0.01330 (6)
O1	−0.38256 (10)	0.25888 (10)	0.79395 (7)	0.02127 (16)
O2	−0.37965 (10)	0.08274 (9)	0.67967 (7)	0.01962 (15)
O3	−0.44670 (9)	0.37665 (9)	0.59896 (7)	0.01834 (14)
N1	0.39588 (10)	0.29545 (10)	0.43756 (8)	0.01497 (15)
N2	1.16999 (11)	0.27158 (11)	0.08368 (8)	0.01660 (16)
C1	0.12637 (12)	0.20179 (11)	0.45697 (8)	0.01394 (16)
H1A	0.1803	0.1600	0.3935	0.017*
C2	−0.04759 (12)	0.18925 (11)	0.51483 (8)	0.01344 (16)
H2A	−0.1106	0.1391	0.4898	0.016*
C3	−0.12775 (11)	0.25131 (11)	0.60985 (8)	0.01259 (15)
C4	−0.03462 (12)	0.32751 (12)	0.64768 (9)	0.01528 (17)
H4A	−0.0885	0.3685	0.7115	0.018*
C5	0.13909 (12)	0.34216 (12)	0.58977 (9)	0.01560 (17)
H5A	0.2013	0.3944	0.6138	0.019*
C6	0.21886 (11)	0.27794 (11)	0.49552 (8)	0.01322 (16)
C7	0.50414 (12)	0.19565 (11)	0.38086 (8)	0.01395 (16)
H7A	0.4650	0.1025	0.3867	0.017*
C8	0.67488 (12)	0.21763 (11)	0.31182 (8)	0.01355 (16)
C9	0.77809 (12)	0.09167 (12)	0.26404 (9)	0.01590 (17)
H9A	0.7332	−0.0032	0.2817	0.019*
C10	0.94259 (13)	0.10588 (12)	0.19236 (9)	0.01669 (17)
H10A	1.0086	0.0198	0.1640	0.020*
C11	1.01332 (12)	0.25146 (12)	0.16084 (8)	0.01427 (16)
C12	0.91019 (12)	0.37647 (12)	0.21180 (9)	0.01533 (17)
H12A	0.9551	0.4708	0.1956	0.018*
C13	0.74652 (12)	0.36035 (12)	0.28410 (9)	0.01506 (17)
H13A	0.6817	0.4442	0.3153	0.018*
C14	1.28157 (13)	0.14184 (13)	0.03449 (10)	0.02023 (19)
H14A	1.2715	0.0372	0.0948	0.024*
H14B	1.4026	0.1575	0.0128	0.024*
C15	1.23208 (15)	0.13989 (16)	−0.07380 (11)	0.0264 (2)
H15A	1.3078	0.0536	−0.1030	0.040*
H15B	1.2442	0.2425	−0.1343	0.040*
H15C	1.1130	0.1223	−0.0524	0.040*
C16	1.24190 (13)	0.42267 (13)	0.04692 (9)	0.01837 (18)
H16A	1.1470	0.5145	0.0429	0.022*
H16B	1.3185	0.4371	−0.0317	0.022*
C17	1.34381 (15)	0.42088 (16)	0.13212 (10)	0.0247 (2)
H17A	1.3825	0.5241	0.1080	0.037*
H17B	1.4434	0.3356	0.1314	0.037*
H17C	1.2698	0.4019	0.2107	0.037*
H1N1	0.427 (2)	0.380 (2)	0.4405 (14)	0.030 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01089 (10)	0.01367 (10)	0.01646 (11)	−0.00400 (7)	−0.00018 (7)	−0.00702 (8)
O1	0.0193 (3)	0.0295 (4)	0.0174 (4)	−0.0095 (3)	0.0027 (3)	−0.0119 (3)
O2	0.0170 (3)	0.0154 (3)	0.0277 (4)	−0.0073 (2)	0.0013 (3)	−0.0102 (3)
O3	0.0130 (3)	0.0177 (3)	0.0254 (4)	−0.0014 (2)	−0.0054 (3)	−0.0078 (3)
N1	0.0111 (3)	0.0178 (4)	0.0183 (4)	−0.0050 (3)	−0.0009 (3)	−0.0085 (3)
N2	0.0127 (3)	0.0200 (4)	0.0166 (4)	−0.0038 (3)	0.0001 (3)	−0.0071 (3)
C1	0.0130 (4)	0.0163 (4)	0.0146 (4)	−0.0044 (3)	−0.0017 (3)	−0.0070 (3)
C2	0.0124 (3)	0.0145 (4)	0.0149 (4)	−0.0042 (3)	−0.0026 (3)	−0.0053 (3)
C3	0.0112 (3)	0.0126 (4)	0.0146 (4)	−0.0031 (3)	−0.0022 (3)	−0.0046 (3)
C4	0.0135 (4)	0.0174 (4)	0.0174 (4)	−0.0038 (3)	−0.0012 (3)	−0.0092 (3)
C5	0.0132 (4)	0.0181 (4)	0.0192 (4)	−0.0045 (3)	−0.0026 (3)	−0.0097 (3)
C6	0.0105 (3)	0.0143 (4)	0.0157 (4)	−0.0038 (3)	−0.0017 (3)	−0.0054 (3)
C7	0.0131 (4)	0.0155 (4)	0.0141 (4)	−0.0039 (3)	−0.0026 (3)	−0.0048 (3)
C8	0.0118 (3)	0.0156 (4)	0.0140 (4)	−0.0032 (3)	−0.0020 (3)	−0.0054 (3)
C9	0.0163 (4)	0.0147 (4)	0.0161 (4)	−0.0038 (3)	−0.0010 (3)	−0.0054 (3)
C10	0.0158 (4)	0.0155 (4)	0.0175 (4)	−0.0019 (3)	−0.0002 (3)	−0.0070 (3)
C11	0.0121 (4)	0.0169 (4)	0.0138 (4)	−0.0022 (3)	−0.0026 (3)	−0.0051 (3)
C12	0.0128 (4)	0.0160 (4)	0.0186 (4)	−0.0039 (3)	−0.0024 (3)	−0.0069 (3)
C13	0.0122 (4)	0.0162 (4)	0.0187 (4)	−0.0025 (3)	−0.0026 (3)	−0.0082 (3)
C14	0.0142 (4)	0.0241 (5)	0.0203 (5)	−0.0009 (3)	0.0008 (3)	−0.0098 (4)
C15	0.0235 (5)	0.0353 (6)	0.0236 (5)	−0.0071 (4)	0.0004 (4)	−0.0163 (5)
C16	0.0157 (4)	0.0231 (5)	0.0162 (4)	−0.0071 (3)	−0.0014 (3)	−0.0050 (4)
C17	0.0195 (4)	0.0374 (6)	0.0221 (5)	−0.0103 (4)	−0.0023 (4)	−0.0130 (4)

Geometric parameters (Å, º) top

S1—O1	1.4511 (8)	C8—C9	1.4148 (13)
S1—O2	1.4555 (7)	C8—C13	1.4152 (13)
S1—O3	1.4685 (8)	C9—C10	1.3714 (13)
S1—C3	1.7814 (9)	C9—H9A	0.9300
N1—C7	1.3146 (12)	C10—C11	1.4256 (13)
N1—C6	1.4206 (11)	C10—H10A	0.9300
N1—H1N1	0.867 (17)	C11—C12	1.4288 (13)
N2—C11	1.3514 (12)	C12—C13	1.3704 (13)
N2—C16	1.4654 (13)	C12—H12A	0.9300
N2—C14	1.4692 (13)	C13—H13A	0.9300
C1—C2	1.3910 (12)	C14—C15	1.5207 (16)
C1—C6	1.3958 (13)	C14—H14A	0.9700
C1—H1A	0.9300	C14—H14B	0.9700
C2—C3	1.3897 (13)	C15—H15A	0.9600
C2—H2A	0.9300	C15—H15B	0.9600
C3—C4	1.3942 (12)	C15—H15C	0.9600
C4—C5	1.3923 (13)	C16—C17	1.5207 (15)
C4—H4A	0.9300	C16—H16A	0.9700
C5—C6	1.3926 (13)	C16—H16B	0.9700
C5—H5A	0.9300	C17—H17A	0.9600
C7—C8	1.4128 (12)	C17—H17B	0.9600
C7—H7A	0.9300	C17—H17C	0.9600

O1—S1—O2	114.51 (5)	C8—C9—H9A	119.2
O1—S1—O3	112.95 (5)	C9—C10—C11	120.59 (9)
O2—S1—O3	112.08 (5)	C9—C10—H10A	119.7
O1—S1—C3	105.86 (4)	C11—C10—H10A	119.7
O2—S1—C3	106.04 (4)	N2—C11—C10	121.17 (9)
O3—S1—C3	104.40 (4)	N2—C11—C12	121.43 (9)
C7—N1—C6	123.77 (8)	C10—C11—C12	117.38 (8)
C7—N1—H1N1	121.8 (11)	C13—C12—C11	121.44 (8)
C6—N1—H1N1	114.4 (11)	C13—C12—H12A	119.3
C11—N2—C16	121.95 (8)	C11—C12—H12A	119.3
C11—N2—C14	122.25 (8)	C12—C13—C8	120.79 (9)
C16—N2—C14	115.76 (8)	C12—C13—H13A	119.6
C2—C1—C6	119.04 (9)	C8—C13—H13A	119.6
C2—C1—H1A	120.5	N2—C14—C15	112.15 (9)
C6—C1—H1A	120.5	N2—C14—H14A	109.2
C3—C2—C1	120.39 (8)	C15—C14—H14A	109.2
C3—C2—H2A	119.8	N2—C14—H14B	109.2
C1—C2—H2A	119.8	C15—C14—H14B	109.2
C2—C3—C4	120.24 (8)	H14A—C14—H14B	107.9
C2—C3—S1	118.97 (7)	C14—C15—H15A	109.5
C4—C3—S1	120.73 (7)	C14—C15—H15B	109.5
C5—C4—C3	119.90 (9)	H15A—C15—H15B	109.5
C5—C4—H4A	120.0	C14—C15—H15C	109.5
C3—C4—H4A	120.0	H15A—C15—H15C	109.5
C4—C5—C6	119.43 (8)	H15B—C15—H15C	109.5
C4—C5—H5A	120.3	N2—C16—C17	111.85 (9)
C6—C5—H5A	120.3	N2—C16—H16A	109.2
C5—C6—C1	121.00 (8)	C17—C16—H16A	109.2
C5—C6—N1	118.26 (8)	N2—C16—H16B	109.2
C1—C6—N1	120.73 (8)	C17—C16—H16B	109.2
N1—C7—C8	125.64 (8)	H16A—C16—H16B	107.9
N1—C7—H7A	117.2	C16—C17—H17A	109.5
C8—C7—H7A	117.2	C16—C17—H17B	109.5
C7—C8—C9	117.96 (8)	H17A—C17—H17B	109.5
C7—C8—C13	123.96 (8)	C16—C17—H17C	109.5
C9—C8—C13	118.04 (8)	H17A—C17—H17C	109.5
C10—C9—C8	121.68 (9)	H17B—C17—H17C	109.5
C10—C9—H9A	119.2

C6—C1—C2—C3	−0.18 (14)	N1—C7—C8—C13	−6.89 (16)
C1—C2—C3—C4	0.32 (14)	C7—C8—C9—C10	177.47 (9)
C1—C2—C3—S1	177.54 (7)	C13—C8—C9—C10	−0.33 (15)
O1—S1—C3—C2	160.63 (8)	C8—C9—C10—C11	−1.77 (15)
O2—S1—C3—C2	38.60 (9)	C16—N2—C11—C10	177.74 (9)
O3—S1—C3—C2	−79.93 (8)	C14—N2—C11—C10	−4.37 (15)
O1—S1—C3—C4	−22.17 (9)	C16—N2—C11—C12	−0.73 (15)
O2—S1—C3—C4	−144.20 (8)	C14—N2—C11—C12	177.16 (9)
O3—S1—C3—C4	97.27 (8)	C9—C10—C11—N2	−175.28 (10)
C2—C3—C4—C5	0.28 (14)	C9—C10—C11—C12	3.24 (14)
S1—C3—C4—C5	−176.89 (7)	N2—C11—C12—C13	175.78 (9)
C3—C4—C5—C6	−1.00 (15)	C10—C11—C12—C13	−2.75 (14)
C4—C5—C6—C1	1.15 (15)	C11—C12—C13—C8	0.74 (15)
C4—C5—C6—N1	179.62 (9)	C7—C8—C13—C12	−176.80 (9)
C2—C1—C6—C5	−0.56 (14)	C9—C8—C13—C12	0.85 (14)
C2—C1—C6—N1	−178.99 (8)	C11—N2—C14—C15	84.88 (12)
C7—N1—C6—C5	153.95 (10)	C16—N2—C14—C15	−97.11 (11)
C7—N1—C6—C1	−27.57 (14)	C11—N2—C16—C17	86.61 (12)
C6—N1—C7—C8	172.99 (9)	C14—N2—C16—C17	−91.41 (11)
N1—C7—C8—C9	175.46 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O3ⁱ	0.865 (18)	2.466 (17)	3.0309 (12)	123.6 (13)
N1—H1N1···O3ⁱⁱ	0.865 (18)	2.076 (18)	2.8989 (12)	158.7 (16)
C7—H7A···O2ⁱⁱⁱ	0.93	2.39	3.2719 (13)	157
C13—H13A···O3ⁱⁱ	0.93	2.40	3.3002 (13)	164
C14—H14A···O1^iv	0.97	2.58	3.4805 (14)	155

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

Experimental details

Crystal data
Chemical formula	C₁₇H₂₀N₂O₃S
M_r	332.42
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.1227 (1), 8.8745 (1), 12.4070 (2)
α, β, γ (°)	69.386 (1), 72.442 (1), 75.509 (1)
V (Å³)	787.63 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.45 × 0.22 × 0.14

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.906, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	24759, 5685, 5040
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.756

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.097, 1.04
No. of reflections	5685
No. of parameters	214
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.77, −0.40

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O3ⁱ	0.865 (18)	2.466 (17)	3.0309 (12)	123.6 (13)
N1—H1N1···O3ⁱⁱ	0.865 (18)	2.076 (18)	2.8989 (12)	158.7 (16)
C7—H7A···O2ⁱⁱⁱ	0.93	2.39	3.2719 (13)	157
C13—H13A···O3ⁱⁱ	0.93	2.40	3.3002 (13)	164
C14—H14A···O1^iv	0.97	2.58	3.4805 (14)	155

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

Footnotes

‡Thomson Reuters ResearcherID: A-5085-2009.

§Additional correspondence author, e-mail: hkfun@usm.my. Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

PR thanks the Thailand Research Fund through the Royal Golden Jubilee PhD Program (grant No. PHD/0314/2552) and the Center of Excellence for Innovation in Chemistry (PERCH-CIC), Office of the Higher Education, Ministry of Education, Thailand, for financial support. The authors also thank Prince of Songkla University and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

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