N′-[1-(2-Hydr­oxy-5-methyl­phen­yl)ethyl­idene]benzene­sulfonohydrazide

Laila, M.; Ali, H.M.; Puvaneswary, S.; Robinson, W.T.; Ng, S.W.

doi:10.1107/S1600536808025932

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1769

doi:10.1107/S1600536808025932

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N′-[1-(2-Hydroxy-5-methylphenyl)ethylidene]benzenesulfonohydrazide

Musalem Laila,^a Hapipah M. Ali,^a Subramaniam Puvaneswary,^a Ward T. Robinson ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 10 July 2008; accepted 11 August 2008; online 16 August 2008)

The two independent molecules in the asymmetric unit of the title compound, C₁₅H₁₆N₂O₃S, are each linked by an N—H⋯O_sulfonyl hydrogen bond into a linear chain that runs along the shortest axis of the triclinic unit cell. The hydroxy groups are engaged in intramolecular hydrogen bonding and the amino N atom shows pyramidal coordination.

Related literature

For 2′-(2-hydroxyphenyl-1-ethylidene)benzenesulfonohydrazide, which adopts a hydrogen-bonded chain structure, see: Ali et al. (2007 ).

Experimental

Crystal data

C₁₅H₁₆N₂O₃S
M_r = 304.36
Triclinic, $[P \overline 1]$
a = 5.1547 (1) Å
b = 17.0321 (2) Å
c = 18.2635 (1) Å
α = 63.192 (1)°
β = 88.577 (1)°
γ = 86.345 (1)°
V = 1428.19 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 100 (2) K
0.18 × 0.14 × 0.06 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.958, T_max = 0.986
12657 measured reflections
6415 independent reflections
5603 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.132
S = 1.04
6415 reflections
399 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.58 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N1	0.84 (3)	1.80 (2)	2.562 (2)	151 (4)
O4—H4o⋯N3	0.85 (3)	1.79 (2)	2.563 (2)	150 (3)
N2—H2n⋯O2ⁱ	0.88 (1)	2.18 (1)	3.040 (2)	168 (2)
N4—H4n⋯O5ⁱⁱ	0.88 (1)	2.07 (1)	2.942 (2)	173 (2)
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z.

Data collection: APEX2 (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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025932/bq2092sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808025932/bq2092Isup2.hkl

checkCIF report

Comment top

2'-(2-Hydroxyphenyl-1-ethylidene)benzenesulfonohydrazide adopts a hydrogen-bonded chain structure; the chain runs along the a-axis of the monoclinic unit cell and the repeat distance is the length of the this axis, i.e., 5.18 Å (Ali et al., 2007). An additional methyl group in the molecule (Scheme I) does not result in any significant difference in both structure and packing (Fig. 1). The two independent molecules are each linked by an N–H···O sulfonyl hydrogen-bond into a linear chain that runs along the shortest axis of the triclinic unit cell; the repeat distance is 5.15 Å. The hydroxy groups are engaged in intramolecular hydrogen bonding (Table 1.).

Related literature top

For 2'-(2-hydroxyphenyl-1-ethylidene)benzenesulfonohydrazide, which adopts a hydrogen-bonded chain structure, see: Ali et al. (2007).

Experimental top

The Schiff base was prepared by refluxing by benzene sulfanohydrazide (0.40 g, 0.64 mmol) and 5-methyl-2-hydroxyacetophenone (0.10 g, 0.64 mmol) in ethanol for 2 h. The product was filtered and recrystallized from ethanol.

Computing details top

Data collection: APEX2 (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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top

Fig. 1. Thermal ellipsoid plot of the asymmetric unit of (I) (Barbour, 2001) at the 70% probability level. Dashed line indicates H-bonding.

N'-[1-(2-Hydroxy-5-methylphenyl)ethylidene]benzenesulfonohydrazide top

Crystal data top

C₁₅H₁₆N₂O₃S	Z = 4
M_r = 304.36	F(000) = 640
Triclinic, P1	D_x = 1.415 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.1547 (1) Å	Cell parameters from 7775 reflections
b = 17.0321 (2) Å	θ = 2.2–30.4°
c = 18.2635 (1) Å	µ = 0.24 mm⁻¹
α = 63.192 (1)°	T = 100 K
β = 88.577 (1)°	Block, colorless
γ = 86.345 (1)°	0.18 × 0.14 × 0.06 mm
V = 1428.19 (4) Å³

Data collection top

Bruker SMART APEX diffractometer	6415 independent reflections
Radiation source: fine-focus sealed tube	5603 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ω scans	θ_max = 27.5°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
T_min = 0.958, T_max = 0.986	k = −22→22
12657 measured reflections	l = −23→22

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0741P)² + 1.3P] where P = (F_o² + 2F_c²)/3
6415 reflections	(Δ/σ)_max = 0.001
399 parameters	Δρ_max = 0.54 e Å⁻³
4 restraints	Δρ_min = −0.58 e Å⁻³

Crystal data top

C₁₅H₁₆N₂O₃S	γ = 86.345 (1)°
M_r = 304.36	V = 1428.19 (4) Å³
Triclinic, P1	Z = 4
a = 5.1547 (1) Å	Mo Kα radiation
b = 17.0321 (2) Å	µ = 0.24 mm⁻¹
c = 18.2635 (1) Å	T = 100 K
α = 63.192 (1)°	0.18 × 0.14 × 0.06 mm
β = 88.577 (1)°

Data collection top

Bruker SMART APEX diffractometer	6415 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5603 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.986	R_int = 0.018
12657 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	4 restraints
wR(F²) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.54 e Å⁻³
6415 reflections	Δρ_min = −0.58 e Å⁻³
399 parameters

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

	x	y	z	U_iso*/U_eq
S1	1.00270 (8)	0.59346 (3)	0.36837 (3)	0.01389 (12)
S2	0.23309 (8)	0.87206 (3)	0.94073 (3)	0.01512 (12)
O1	1.1834 (3)	0.79133 (9)	0.43334 (9)	0.0198 (3)
O2	1.2673 (3)	0.59821 (9)	0.38815 (8)	0.0181 (3)
O3	0.9214 (3)	0.51803 (9)	0.36199 (9)	0.0190 (3)
O4	0.1038 (3)	0.73122 (10)	0.80833 (9)	0.0238 (3)
O5	−0.0223 (3)	0.84056 (10)	0.94695 (9)	0.0206 (3)
O6	0.3106 (3)	0.90879 (9)	0.99282 (9)	0.0196 (3)
N1	0.8800 (3)	0.66835 (10)	0.45822 (10)	0.0153 (3)
N2	0.8209 (3)	0.59890 (11)	0.44147 (10)	0.0150 (3)
N3	0.3956 (3)	0.74366 (11)	0.91380 (10)	0.0163 (3)
N4	0.4405 (3)	0.78638 (11)	0.96235 (10)	0.0159 (3)
C1	1.0427 (4)	0.80153 (13)	0.49302 (12)	0.0165 (4)
C2	1.1112 (4)	0.86743 (13)	0.51253 (13)	0.0200 (4)
H2	1.2525	0.9023	0.4851	0.024*
C3	0.9752 (4)	0.88270 (13)	0.57162 (13)	0.0205 (4)
H3	1.0244	0.9282	0.5840	0.025*
C4	0.7677 (4)	0.83279 (13)	0.61327 (12)	0.0189 (4)
C5	0.7016 (4)	0.76637 (13)	0.59405 (12)	0.0173 (4)
H5	0.5617	0.7313	0.6225	0.021*
C6	0.8335 (4)	0.74898 (12)	0.53418 (11)	0.0151 (4)
C7	0.6197 (4)	0.84927 (15)	0.67793 (14)	0.0243 (4)
H7A	0.4382	0.8351	0.6783	0.037*
H7B	0.6264	0.9114	0.6656	0.037*
H7C	0.6985	0.8120	0.7318	0.037*
C8	0.7526 (4)	0.67782 (12)	0.51600 (11)	0.0152 (4)
C9	0.5429 (4)	0.61962 (13)	0.56463 (13)	0.0208 (4)
H9A	0.4909	0.5847	0.5376	0.031*
H9B	0.3926	0.6559	0.5682	0.031*
H9C	0.6077	0.5800	0.6199	0.031*
C10	0.9242 (4)	0.68803 (12)	0.27615 (11)	0.0153 (4)
C11	0.7132 (4)	0.68724 (14)	0.23050 (12)	0.0200 (4)
H11	0.6139	0.6367	0.2489	0.024*
C12	0.6499 (4)	0.76133 (14)	0.15765 (12)	0.0219 (4)
H12	0.5065	0.7616	0.1258	0.026*
C13	0.7956 (4)	0.83520 (14)	0.13098 (12)	0.0224 (4)
H13	0.7512	0.8859	0.0811	0.027*
C14	1.0053 (4)	0.83500 (14)	0.17703 (13)	0.0242 (4)
H14	1.1050	0.8855	0.1584	0.029*
C15	1.0708 (4)	0.76134 (14)	0.25038 (12)	0.0206 (4)
H15	1.2136	0.7612	0.2823	0.025*
C16	0.2653 (4)	0.66099 (14)	0.81883 (12)	0.0194 (4)
C17	0.2155 (4)	0.61764 (15)	0.77206 (13)	0.0230 (4)
H17	0.0730	0.6380	0.7348	0.028*
C18	0.3706 (4)	0.54571 (14)	0.77928 (13)	0.0222 (4)
H18	0.3328	0.5170	0.7470	0.027*
C19	0.5829 (4)	0.51392 (14)	0.83316 (13)	0.0209 (4)
C20	0.6317 (4)	0.55738 (13)	0.87953 (12)	0.0189 (4)
H20	0.7759	0.5367	0.9161	0.023*
C21	0.4775 (4)	0.63059 (13)	0.87480 (12)	0.0171 (4)
C22	0.7530 (4)	0.43515 (15)	0.84084 (15)	0.0273 (5)
H22A	0.9231	0.4364	0.8630	0.041*
H22B	0.7753	0.4369	0.7867	0.041*
H22C	0.6709	0.3810	0.8779	0.041*
C23	0.5394 (4)	0.67411 (13)	0.92575 (11)	0.0162 (4)
C24	0.7550 (4)	0.63615 (13)	0.98790 (12)	0.0196 (4)
H24A	0.7488	0.6660	1.0229	0.029*
H24B	0.9226	0.6446	0.9596	0.029*
H24C	0.7344	0.5731	1.0217	0.029*
C25	0.2788 (4)	0.94842 (12)	0.83776 (11)	0.0157 (4)
C26	0.4827 (4)	1.00410 (13)	0.81963 (13)	0.0202 (4)
H26	0.5954	1.0000	0.8617	0.024*
C27	0.5177 (4)	1.06564 (14)	0.73883 (13)	0.0225 (4)
H27	0.6577	1.1034	0.7251	0.027*
C28	0.3492 (4)	1.07231 (13)	0.67788 (13)	0.0210 (4)
H28	0.3721	1.1154	0.6229	0.025*
C29	0.1478 (4)	1.01618 (14)	0.69714 (13)	0.0215 (4)
H29	0.0333	1.0210	0.6551	0.026*
C30	0.1120 (4)	0.95307 (13)	0.77718 (12)	0.0185 (4)
H30	−0.0240	0.9138	0.7903	0.022*
H1O	1.110 (6)	0.7524 (18)	0.427 (2)	0.057 (10)*
H4O	0.165 (6)	0.752 (2)	0.8385 (17)	0.043 (8)*
H2N	0.657 (2)	0.5927 (17)	0.4337 (16)	0.025 (6)*
H4N	0.600 (2)	0.8017 (16)	0.9621 (16)	0.022 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0143 (2)	0.0138 (2)	0.0141 (2)	−0.00056 (16)	−0.00083 (16)	−0.00670 (17)
S2	0.0133 (2)	0.0169 (2)	0.0150 (2)	−0.00203 (16)	−0.00012 (16)	−0.00687 (18)
O1	0.0216 (7)	0.0193 (7)	0.0200 (7)	−0.0062 (6)	0.0044 (5)	−0.0098 (6)
O2	0.0157 (6)	0.0183 (7)	0.0186 (7)	−0.0004 (5)	−0.0014 (5)	−0.0068 (6)
O3	0.0213 (7)	0.0173 (7)	0.0206 (7)	−0.0016 (5)	−0.0016 (5)	−0.0103 (6)
O4	0.0222 (7)	0.0268 (8)	0.0248 (8)	0.0032 (6)	−0.0080 (6)	−0.0140 (7)
O5	0.0145 (6)	0.0248 (7)	0.0205 (7)	−0.0042 (5)	0.0008 (5)	−0.0080 (6)
O6	0.0217 (7)	0.0225 (7)	0.0175 (7)	−0.0013 (6)	−0.0007 (5)	−0.0117 (6)
N1	0.0181 (8)	0.0142 (7)	0.0152 (7)	−0.0022 (6)	−0.0020 (6)	−0.0078 (6)
N2	0.0160 (7)	0.0160 (8)	0.0157 (7)	−0.0036 (6)	0.0015 (6)	−0.0091 (6)
N3	0.0169 (7)	0.0173 (8)	0.0162 (8)	−0.0034 (6)	−0.0004 (6)	−0.0084 (6)
N4	0.0152 (7)	0.0167 (8)	0.0166 (8)	−0.0014 (6)	−0.0026 (6)	−0.0080 (6)
C1	0.0182 (9)	0.0153 (9)	0.0140 (8)	0.0000 (7)	−0.0023 (7)	−0.0049 (7)
C2	0.0217 (9)	0.0157 (9)	0.0205 (9)	−0.0026 (7)	−0.0030 (7)	−0.0060 (8)
C3	0.0239 (10)	0.0169 (9)	0.0230 (10)	0.0006 (7)	−0.0065 (8)	−0.0110 (8)
C4	0.0207 (9)	0.0191 (9)	0.0175 (9)	0.0042 (7)	−0.0052 (7)	−0.0093 (8)
C5	0.0178 (9)	0.0168 (9)	0.0170 (9)	0.0005 (7)	−0.0023 (7)	−0.0074 (7)
C6	0.0182 (9)	0.0131 (8)	0.0132 (8)	0.0004 (7)	−0.0028 (7)	−0.0053 (7)
C7	0.0257 (10)	0.0265 (11)	0.0271 (11)	0.0034 (8)	−0.0021 (8)	−0.0181 (9)
C8	0.0164 (8)	0.0135 (8)	0.0132 (8)	0.0003 (7)	−0.0024 (7)	−0.0039 (7)
C9	0.0233 (10)	0.0181 (9)	0.0222 (10)	−0.0051 (8)	0.0081 (8)	−0.0102 (8)
C10	0.0165 (8)	0.0164 (9)	0.0127 (8)	−0.0003 (7)	0.0000 (7)	−0.0064 (7)
C11	0.0212 (9)	0.0202 (10)	0.0191 (9)	−0.0035 (7)	−0.0014 (7)	−0.0091 (8)
C12	0.0230 (10)	0.0260 (10)	0.0169 (9)	0.0012 (8)	−0.0050 (7)	−0.0101 (8)
C13	0.0272 (10)	0.0219 (10)	0.0145 (9)	0.0026 (8)	0.0006 (8)	−0.0057 (8)
C14	0.0290 (11)	0.0181 (10)	0.0225 (10)	−0.0055 (8)	−0.0002 (8)	−0.0061 (8)
C15	0.0217 (9)	0.0210 (10)	0.0189 (9)	−0.0029 (8)	−0.0018 (7)	−0.0086 (8)
C16	0.0186 (9)	0.0218 (10)	0.0176 (9)	−0.0035 (7)	0.0003 (7)	−0.0085 (8)
C17	0.0219 (10)	0.0283 (11)	0.0197 (10)	−0.0052 (8)	−0.0019 (8)	−0.0111 (9)
C18	0.0270 (10)	0.0257 (10)	0.0177 (9)	−0.0087 (8)	0.0045 (8)	−0.0124 (8)
C19	0.0213 (9)	0.0221 (10)	0.0208 (10)	−0.0073 (8)	0.0050 (8)	−0.0105 (8)
C20	0.0197 (9)	0.0197 (9)	0.0181 (9)	−0.0039 (7)	0.0011 (7)	−0.0091 (8)
C21	0.0177 (9)	0.0190 (9)	0.0157 (9)	−0.0050 (7)	0.0017 (7)	−0.0083 (8)
C22	0.0288 (11)	0.0269 (11)	0.0325 (12)	−0.0031 (9)	0.0015 (9)	−0.0188 (10)
C23	0.0161 (9)	0.0169 (9)	0.0138 (8)	−0.0040 (7)	0.0009 (7)	−0.0049 (7)
C24	0.0206 (9)	0.0177 (9)	0.0191 (9)	−0.0008 (7)	−0.0034 (7)	−0.0070 (8)
C25	0.0167 (9)	0.0146 (8)	0.0136 (8)	0.0002 (7)	0.0003 (7)	−0.0047 (7)
C26	0.0182 (9)	0.0200 (9)	0.0209 (10)	−0.0019 (7)	−0.0025 (7)	−0.0075 (8)
C27	0.0191 (9)	0.0174 (9)	0.0262 (11)	−0.0029 (7)	0.0015 (8)	−0.0054 (8)
C28	0.0235 (10)	0.0184 (9)	0.0180 (9)	0.0028 (8)	0.0017 (7)	−0.0060 (8)
C29	0.0243 (10)	0.0233 (10)	0.0188 (9)	0.0019 (8)	−0.0038 (8)	−0.0115 (8)
C30	0.0184 (9)	0.0195 (9)	0.0192 (9)	−0.0012 (7)	−0.0018 (7)	−0.0099 (8)

Geometric parameters (Å, º) top

S1—O3	1.4303 (14)	C11—C12	1.387 (3)
S1—O2	1.4360 (14)	C11—H11	0.9500
S1—N2	1.6455 (16)	C12—C13	1.390 (3)
S1—C10	1.7603 (19)	C12—H12	0.9500
S2—O6	1.4296 (14)	C13—C14	1.385 (3)
S2—O5	1.4355 (14)	C13—H13	0.9500
S2—N4	1.6526 (17)	C14—C15	1.391 (3)
S2—C25	1.7591 (19)	C14—H14	0.9500
O1—C1	1.364 (2)	C15—H15	0.9500
O1—H1O	0.84 (3)	C16—C17	1.394 (3)
O4—C16	1.355 (2)	C16—C21	1.419 (3)
O4—H4O	0.85 (3)	C17—C18	1.376 (3)
N1—C8	1.295 (2)	C17—H17	0.9500
N1—N2	1.401 (2)	C18—C19	1.399 (3)
N2—H2N	0.879 (10)	C18—H18	0.9500
N3—C23	1.290 (3)	C19—C20	1.389 (3)
N3—N4	1.408 (2)	C19—C22	1.508 (3)
N4—H4N	0.877 (10)	C20—C21	1.405 (3)
C1—C2	1.389 (3)	C20—H20	0.9500
C1—C6	1.416 (3)	C21—C23	1.478 (3)
C2—C3	1.384 (3)	C22—H22A	0.9800
C2—H2	0.9500	C22—H22B	0.9800
C3—C4	1.392 (3)	C22—H22C	0.9800
C3—H3	0.9500	C23—C24	1.500 (3)
C4—C5	1.390 (3)	C24—H24A	0.9800
C4—C7	1.511 (3)	C24—H24B	0.9800
C5—C6	1.406 (3)	C24—H24C	0.9800
C5—H5	0.9500	C25—C30	1.389 (3)
C6—C8	1.479 (2)	C25—C26	1.393 (3)
C7—H7A	0.9800	C26—C27	1.387 (3)
C7—H7B	0.9800	C26—H26	0.9500
C7—H7C	0.9800	C27—C28	1.388 (3)
C8—C9	1.495 (3)	C27—H27	0.9500
C9—H9A	0.9800	C28—C29	1.386 (3)
C9—H9B	0.9800	C28—H28	0.9500
C9—H9C	0.9800	C29—C30	1.386 (3)
C10—C15	1.387 (3)	C29—H29	0.9500
C10—C11	1.391 (3)	C30—H30	0.9500

O3—S1—O2	120.83 (8)	C11—C12—H12	119.9
O3—S1—N2	104.70 (8)	C13—C12—H12	119.9
O2—S1—N2	106.84 (8)	C14—C13—C12	120.07 (19)
O3—S1—C10	108.61 (9)	C14—C13—H13	120.0
O2—S1—C10	107.30 (9)	C12—C13—H13	120.0
N2—S1—C10	107.97 (9)	C13—C14—C15	120.38 (19)
O6—S2—O5	120.70 (9)	C13—C14—H14	119.8
O6—S2—N4	104.46 (8)	C15—C14—H14	119.8
O5—S2—N4	106.50 (9)	C10—C15—C14	118.93 (18)
O6—S2—C25	109.14 (9)	C10—C15—H15	120.5
O5—S2—C25	107.40 (9)	C14—C15—H15	120.5
N4—S2—C25	108.03 (9)	O4—C16—C17	117.22 (18)
C1—O1—H1O	104 (3)	O4—C16—C21	122.92 (17)
C16—O4—H4O	105 (2)	C17—C16—C21	119.85 (19)
C8—N1—N2	118.12 (16)	C18—C17—C16	120.71 (19)
N1—N2—S1	112.74 (12)	C18—C17—H17	119.6
N1—N2—H2N	118.6 (17)	C16—C17—H17	119.6
S1—N2—H2N	110.1 (17)	C17—C18—C19	121.38 (18)
C23—N3—N4	118.41 (16)	C17—C18—H18	119.3
N3—N4—S2	111.80 (12)	C19—C18—H18	119.3
N3—N4—H4N	115.8 (17)	C20—C19—C18	117.66 (19)
S2—N4—H4N	110.0 (17)	C20—C19—C22	121.06 (19)
O1—C1—C2	117.07 (17)	C18—C19—C22	121.29 (18)
O1—C1—C6	123.00 (17)	C19—C20—C21	123.01 (18)
C2—C1—C6	119.92 (18)	C19—C20—H20	118.5
C3—C2—C1	120.50 (19)	C21—C20—H20	118.5
C3—C2—H2	119.8	C20—C21—C16	117.39 (17)
C1—C2—H2	119.8	C20—C21—C23	120.48 (17)
C2—C3—C4	121.39 (18)	C16—C21—C23	122.13 (18)
C2—C3—H3	119.3	C19—C22—H22A	109.5
C4—C3—H3	119.3	C19—C22—H22B	109.5
C5—C4—C3	117.86 (18)	H22A—C22—H22B	109.5
C5—C4—C7	120.74 (19)	C19—C22—H22C	109.5
C3—C4—C7	121.40 (18)	H22A—C22—H22C	109.5
C4—C5—C6	122.59 (19)	H22B—C22—H22C	109.5
C4—C5—H5	118.7	N3—C23—C21	115.90 (17)
C6—C5—H5	118.7	N3—C23—C24	123.93 (17)
C5—C6—C1	117.73 (17)	C21—C23—C24	120.16 (17)
C5—C6—C8	120.05 (17)	C23—C24—H24A	109.5
C1—C6—C8	122.22 (17)	C23—C24—H24B	109.5
C4—C7—H7A	109.5	H24A—C24—H24B	109.5
C4—C7—H7B	109.5	C23—C24—H24C	109.5
H7A—C7—H7B	109.5	H24A—C24—H24C	109.5
C4—C7—H7C	109.5	H24B—C24—H24C	109.5
H7A—C7—H7C	109.5	C30—C25—C26	121.68 (18)
H7B—C7—H7C	109.5	C30—C25—S2	120.18 (15)
N1—C8—C6	115.73 (17)	C26—C25—S2	118.14 (15)
N1—C8—C9	123.48 (17)	C27—C26—C25	118.62 (18)
C6—C8—C9	120.75 (16)	C27—C26—H26	120.7
C8—C9—H9A	109.5	C25—C26—H26	120.7
C8—C9—H9B	109.5	C26—C27—C28	120.36 (19)
H9A—C9—H9B	109.5	C26—C27—H27	119.8
C8—C9—H9C	109.5	C28—C27—H27	119.8
H9A—C9—H9C	109.5	C29—C28—C27	120.14 (19)
H9B—C9—H9C	109.5	C29—C28—H28	119.9
C15—C10—C11	121.32 (18)	C27—C28—H28	119.9
C15—C10—S1	120.15 (14)	C30—C29—C28	120.52 (19)
C11—C10—S1	118.53 (15)	C30—C29—H29	119.7
C12—C11—C10	119.01 (19)	C28—C29—H29	119.7
C12—C11—H11	120.5	C29—C30—C25	118.66 (18)
C10—C11—H11	120.5	C29—C30—H30	120.7
C11—C12—C13	120.27 (18)	C25—C30—H30	120.7

C8—N1—N2—S1	−178.55 (13)	C12—C13—C14—C15	−0.4 (3)
O3—S1—N2—N1	178.10 (12)	C11—C10—C15—C14	−0.5 (3)
O2—S1—N2—N1	48.83 (14)	S1—C10—C15—C14	179.65 (16)
C10—S1—N2—N1	−66.31 (14)	C13—C14—C15—C10	0.6 (3)
C23—N3—N4—S2	−178.21 (14)	O4—C16—C17—C18	−179.93 (19)
O6—S2—N4—N3	−178.19 (12)	C21—C16—C17—C18	−0.3 (3)
O5—S2—N4—N3	53.04 (14)	C16—C17—C18—C19	−0.3 (3)
C25—S2—N4—N3	−62.08 (14)	C17—C18—C19—C20	0.2 (3)
O1—C1—C2—C3	179.06 (17)	C17—C18—C19—C22	−179.9 (2)
C6—C1—C2—C3	−0.5 (3)	C18—C19—C20—C21	0.4 (3)
C1—C2—C3—C4	0.2 (3)	C22—C19—C20—C21	−179.54 (19)
C2—C3—C4—C5	0.4 (3)	C19—C20—C21—C16	−0.9 (3)
C2—C3—C4—C7	179.82 (18)	C19—C20—C21—C23	−179.97 (18)
C3—C4—C5—C6	−0.8 (3)	O4—C16—C21—C20	−179.57 (18)
C7—C4—C5—C6	179.81 (18)	C17—C16—C21—C20	0.8 (3)
C4—C5—C6—C1	0.5 (3)	O4—C16—C21—C23	−0.5 (3)
C4—C5—C6—C8	−179.50 (17)	C17—C16—C21—C23	179.88 (18)
O1—C1—C6—C5	−179.38 (17)	N4—N3—C23—C21	178.11 (16)
C2—C1—C6—C5	0.1 (3)	N4—N3—C23—C24	−0.7 (3)
O1—C1—C6—C8	0.6 (3)	C20—C21—C23—N3	176.27 (18)
C2—C1—C6—C8	−179.87 (17)	C16—C21—C23—N3	−2.8 (3)
N2—N1—C8—C6	176.62 (15)	C20—C21—C23—C24	−4.9 (3)
N2—N1—C8—C9	−1.1 (3)	C16—C21—C23—C24	176.08 (18)
C5—C6—C8—N1	177.95 (17)	O6—S2—C25—C30	−147.06 (15)
C1—C6—C8—N1	−2.0 (3)	O5—S2—C25—C30	−14.60 (18)
C5—C6—C8—C9	−4.2 (3)	N4—S2—C25—C30	99.92 (16)
C1—C6—C8—C9	175.76 (18)	O6—S2—C25—C26	31.95 (18)
O3—S1—C10—C15	−151.83 (16)	O5—S2—C25—C26	164.42 (15)
O2—S1—C10—C15	−19.67 (18)	N4—S2—C25—C26	−81.06 (17)
N2—S1—C10—C15	95.17 (17)	C30—C25—C26—C27	0.1 (3)
O3—S1—C10—C11	28.32 (18)	S2—C25—C26—C27	−178.86 (16)
O2—S1—C10—C11	160.48 (15)	C25—C26—C27—C28	1.2 (3)
N2—S1—C10—C11	−84.68 (16)	C26—C27—C28—C29	−1.3 (3)
C15—C10—C11—C12	0.3 (3)	C27—C28—C29—C30	0.1 (3)
S1—C10—C11—C12	−179.87 (15)	C28—C29—C30—C25	1.2 (3)
C10—C11—C12—C13	−0.1 (3)	C26—C25—C30—C29	−1.3 (3)
C11—C12—C13—C14	0.2 (3)	S2—C25—C30—C29	177.65 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.84 (3)	1.80 (2)	2.562 (2)	151 (4)
O4—H4o···N3	0.85 (3)	1.79 (2)	2.563 (2)	150 (3)
N2—H2n···O2ⁱ	0.88 (1)	2.18 (1)	3.040 (2)	168 (2)
N4—H4n···O5ⁱⁱ	0.88 (1)	2.07 (1)	2.942 (2)	173 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₆N₂O₃S
M_r	304.36
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	5.1547 (1), 17.0321 (2), 18.2635 (1)
α, β, γ (°)	63.192 (1), 88.577 (1), 86.345 (1)
V (Å³)	1428.19 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.18 × 0.14 × 0.06

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.958, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	12657, 6415, 5603
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.132, 1.05
No. of reflections	6415
No. of parameters	399
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.58

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.84 (3)	1.80 (2)	2.562 (2)	151 (4)
O4—H4o···N3	0.85 (3)	1.79 (2)	2.563 (2)	150 (3)
N2—H2n···O2ⁱ	0.88 (1)	2.18 (1)	3.040 (2)	168 (2)
N4—H4n···O5ⁱⁱ	0.88 (1)	2.07 (1)	2.942 (2)	173 (2)

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

Acknowledgements

We thank the Science Fund (12–02-03–2031, 12–02-03–2051) and the University of Malaya (PJP) for supporting this study. We are grateful to the University of Malaya for the purchase of the diffractometer.

References

Ali, H. M., Laila, M., Wan Jefrey, B. & Ng, S. W. (2007). Acta Cryst. E63, o1617–o1618. Web of Science CSD CrossRef IUCr Journals Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar