1,3-Dimeth­oxy-2,3-dihydro-1H-isoindole-2-carbothio­amide

Maliha, B.; Tariq, M.I.; Tahir, M.N.; Hussain, I.; Ali, M.

doi:10.1107/S1600536808040075

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o41

doi:10.1107/S1600536808040075

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1,3-Dimethoxy-2,3-dihydro-1H-isoindole-2-carbothioamide

Bushra Maliha,^a Muhammad Ilyas Tariq,^b M. Nawaz Tahir,^c ^* Ishtiaq Hussain ^a and Muhammad Ali ^d

^aInstitute of Chemistry, University of the Punjab, Lahore-54590, Pakistan, ^bDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan, ^cDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and ^dDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 26 November 2008; accepted 27 November 2008; online 6 December 2008)

In the molecule of the title compound, C₁₁H₁₄N₂O₂S, the five-membered ring adopts an envelope conformation and an intramolecular N—H⋯O hydrogen bond occurs. Intramolecular N—H⋯O, C—H⋯S and C—H⋯N hydrogen bonds result in the formation of two five- and one six-membered rings, having twisted conformations. In the crystal structure, intermolecular N—H⋯O, N—H⋯S and C—H⋯S hydrogen bonds link the molecules, forming polymeric sheets. The π–π contacts between the isoindole ring systems, [centroid–centroid distances = 3.5883 (8) and 4.0619 (8) Å] may further stabilize the structure. A C—H⋯π interactions also occur.

Related literature

For general background to isoindoles and their derivatives, see: Mancilla et al. (2007 ); Toru et al. (1986 ). For related structures, see: Maliha et al. (2007 ); Maliha, Hussain et al. (2008 ); Maliha, Tariq et al. (2008 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₁H₁₄N₂O₂S
M_r = 238.30
Monoclinic, C 2/c
a = 15.4577 (8) Å
b = 8.6455 (5) Å
c = 18.2184 (10) Å
β = 107.322 (2)°
V = 2324.3 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 100 (2) K
0.20 × 0.16 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.945, T_max = 0.969
18083 measured reflections
2894 independent reflections
2471 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.110
S = 1.01
2894 reflections
159 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N⋯O1ⁱ	0.891 (17)	2.087 (17)	2.9738 (14)	172.9 (15)
N2—H2N⋯O1	0.826 (17)	2.413 (17)	2.9867 (14)	127.3 (14)
N2—H2N⋯S1ⁱⁱ	0.826 (17)	2.646 (17)	3.2857 (11)	135.4 (15)
C3—H3⋯S1ⁱⁱⁱ	0.95	2.79	3.7362 (13)	178
C1—H1⋯CgB^iv	0.98	2.500 (17)	3.4059 (13)	155.1 (1)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y-1, z; (iv) $[-x, y, -z+{\script{1\over 2}}]$ . CgB is the centroids of the N1/C1/C2/C7/C8 ring.

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: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2003 ); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks text, I. DOI: 10.1107/S1600536808040075/hk2586sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808040075/hk2586Isup2.hkl

checkCIF report

Comment top

Isoindoles and their derivatives are of great pharmaceutical importance (Mancilla et al., 2007). Certain derivatives of isoindoles have shown a wide range of herbicidal activities (Toru et al., 1986). The title compound is in continuation of the syntheses of isoindoles along with their derivatives and characterizations with the help of X-ray crystallography (Maliha et al., 2007; Maliha, Hussain et al., 2008; Maliha, Tariq et al., 2008).

In the molecule of title compound (Fig 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Ring A (C2-C7) is, of course, planar, while the five-membered ring B (N1/C1/C2/C7/C8) adopts envelope conformation with C8 atom displaced by 0.141 (3) Å from the plane of the other ring atoms. The intramolecular N-H···O, C-H···S and C-H···N hydrogen bonds (Table 1) result in the formation of two five- and one six-membered rings: C (N1/S1/C8/C11/H8), D (O1/N1/N2/C1/C11/H2N) and E (O1/N1/C1/C9/H9C), respectively, having twisted conformations.

In the crystal structure, intermolecular N-H···O, N-H···S and C-H···S hydrogen bonds (Table 1) link the molecules to form polymeric sheets, in which the orientations of O—CH₃ groups cause to the R and S-configurations at the carbon atoms, C1 and C8, respectively. The behaviour of the O—CH₃ groups are not identical, because only opposite of S-atom is involved in intramolecular H-bonding. The π-π contacts between the isoindole ring systems, CgB—CgBⁱ and CgB—CgAⁱ [symmetry code: (i) -x, y, 1/2 - z, where CgA and CgB are centroids of the rings A (C2-C7) and B (N1/C1/C2/C7/C8)] may further stabilize the structure, with centroid-centroid distances of 3.5883 (8) Å and 4.0619 (8) Å. There also exist two C–H···π interactions (Table 1).

Related literature top

For general background to isoindoles and their derivative, see: Mancilla et al. (2007); Toru et al. (1986). For relatesd structures, see: Maliha et al. (2007); Maliha, Hussain et al. (2008); Maliha, Tariq et al. (2008). For bond-length data, see: Allen et al. (1987). CgA and CgB are centroids of the C2–C7 andN1/C1/C2/C7/C8 rings, respectively.

Experimental top

For the preparation of the title conpound, ortho-phthaldehyde (1.34 g, 200 mmol) and thiourea (0.76 g, 200 mmol) were added to distilled water (250 ml), and aqueous NaOH (5 ml, 5%) was added dropwise with constant stirring. After 3 h, a colorless precipitate was obtained, which was washed with hexane, ethanol, acetone and methanol, respectively. Then, it was further refluxed in methanol for 2 h, and left to stand overnight. The deep red tiny crystals settled down, which were washed with ether, hexane and cold methanol, respectively. Crystals suitable for X-ray analysis were obtained from a solution of acetone/methanol mixture by slow evaporation at room temperature.

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: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: 'WinGX publication routines (Farrugia, 1999) and PLATON'.

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

(1R,3S)-1,3-dimethoxy-2,3-dihydro-1H-isoindole-2-carbothioamide top

Crystal data top

C₁₁H₁₄N₂O₂S	F(000) = 1008
M_r = 238.30	D_x = 1.362 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1295 reflections
a = 15.4577 (8) Å	θ = 2.3–28.3°
b = 8.6455 (5) Å	µ = 0.27 mm⁻¹
c = 18.2184 (10) Å	T = 100 K
β = 107.322 (2)°	Prismatic, red
V = 2324.3 (2) Å³	0.20 × 0.16 × 0.12 mm
Z = 8

Data collection top

Bruker Kappa APEXII CCD diffractometer	2894 independent reflections
Radiation source: fine-focus sealed tube	2471 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
Detector resolution: 7.40 pixels mm^-1	θ_max = 28.3°, θ_min = 2.3°
ω scans	h = −20→20
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −11→11
T_min = 0.945, T_max = 0.969	l = −24→23
18083 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0799P)² + 0.660P] where P = (F_o² + 2F_c²)/3
2894 reflections	(Δ/σ)_max = 0.002
159 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₁H₁₄N₂O₂S	V = 2324.3 (2) Å³
M_r = 238.30	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 15.4577 (8) Å	µ = 0.27 mm⁻¹
b = 8.6455 (5) Å	T = 100 K
c = 18.2184 (10) Å	0.20 × 0.16 × 0.12 mm
β = 107.322 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2894 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2471 reflections with I > 2σ(I)
T_min = 0.945, T_max = 0.969	R_int = 0.032
18083 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.44 e Å⁻³
2894 reflections	Δρ_min = −0.37 e Å⁻³
159 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.11517 (2)	0.49877 (3)	0.21266 (2)	0.0204 (1)
O1	0.14785 (6)	−0.02891 (10)	0.15401 (5)	0.0138 (2)
O2	−0.01835 (6)	0.30468 (10)	0.05803 (5)	0.0171 (2)
N1	0.07220 (7)	0.20405 (11)	0.17484 (6)	0.0120 (3)
N2	0.21825 (7)	0.25081 (12)	0.24928 (6)	0.0148 (3)
C1	0.08273 (8)	0.03577 (13)	0.18556 (7)	0.0110 (3)
C2	−0.01336 (8)	−0.02006 (14)	0.15260 (7)	0.0117 (3)
C3	−0.04573 (8)	−0.17035 (14)	0.15157 (7)	0.0154 (3)
C4	−0.13922 (9)	−0.19328 (15)	0.12533 (8)	0.0174 (3)
C5	−0.19841 (9)	−0.06902 (15)	0.10138 (7)	0.0167 (3)
C6	−0.16516 (8)	0.08113 (14)	0.10175 (7)	0.0141 (3)
C7	−0.07174 (8)	0.10380 (13)	0.12693 (7)	0.0119 (3)
C8	−0.01925 (8)	0.25238 (13)	0.13215 (7)	0.0128 (3)
C9	0.12812 (10)	−0.01421 (17)	0.07232 (8)	0.0221 (4)
C10	−0.08727 (10)	0.41497 (17)	0.02569 (9)	0.0275 (4)
C11	0.13705 (8)	0.30768 (14)	0.21217 (7)	0.0125 (3)
H1	0.1091 (11)	0.0123 (16)	0.2398 (10)	0.0132*
H1N	0.2602 (11)	0.318 (2)	0.2748 (9)	0.0178*
H2N	0.2325 (11)	0.160 (2)	0.2447 (9)	0.0178*
H3	−0.00537	−0.25487	0.16825	0.0184*
H4	−0.16291	−0.29503	0.12374	0.0208*
H5	−0.26194	−0.08673	0.08467	0.0201*
H6	−0.20533	0.16594	0.08519	0.0169*
H8	−0.0393 (10)	0.3344 (18)	0.1604 (9)	0.0153*
H9A	0.07524	−0.07779	0.04676	0.0265*
H9B	0.18042	−0.04909	0.05681	0.0265*
H9C	0.11520	0.09429	0.05753	0.0265*
H10A	−0.14679	0.36807	0.01925	0.0330*
H10B	−0.08290	0.44837	−0.02449	0.0330*
H10C	−0.07967	0.50456	0.05998	0.0330*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0134 (2)	0.0095 (2)	0.0347 (2)	0.0004 (1)	0.0018 (2)	−0.0017 (1)
O1	0.0126 (4)	0.0154 (4)	0.0131 (4)	0.0039 (3)	0.0032 (3)	−0.0015 (3)
O2	0.0180 (4)	0.0163 (4)	0.0155 (4)	0.0019 (3)	0.0025 (4)	0.0062 (3)
N1	0.0103 (5)	0.0095 (4)	0.0144 (5)	0.0014 (3)	0.0010 (4)	0.0007 (4)
N2	0.0121 (5)	0.0107 (5)	0.0195 (5)	0.0001 (4)	0.0013 (4)	−0.0006 (4)
C1	0.0115 (5)	0.0089 (5)	0.0119 (5)	0.0016 (4)	0.0024 (4)	0.0000 (4)
C2	0.0105 (5)	0.0133 (5)	0.0109 (5)	0.0006 (4)	0.0025 (4)	−0.0007 (4)
C3	0.0161 (6)	0.0124 (5)	0.0162 (6)	0.0005 (4)	0.0026 (5)	−0.0008 (4)
C4	0.0182 (6)	0.0145 (6)	0.0184 (6)	−0.0043 (4)	0.0040 (5)	−0.0014 (5)
C5	0.0123 (5)	0.0208 (6)	0.0160 (6)	−0.0035 (5)	0.0027 (5)	−0.0001 (5)
C6	0.0126 (5)	0.0160 (6)	0.0130 (6)	0.0016 (4)	0.0027 (4)	0.0011 (4)
C7	0.0134 (5)	0.0121 (5)	0.0098 (5)	0.0006 (4)	0.0030 (4)	−0.0004 (4)
C8	0.0113 (5)	0.0116 (5)	0.0138 (5)	0.0013 (4)	0.0013 (4)	0.0011 (4)
C9	0.0224 (7)	0.0315 (8)	0.0134 (6)	0.0055 (5)	0.0069 (5)	−0.0018 (5)
C10	0.0194 (6)	0.0282 (7)	0.0313 (8)	0.0045 (5)	0.0021 (6)	0.0163 (6)
C11	0.0127 (5)	0.0127 (5)	0.0126 (5)	−0.0006 (4)	0.0046 (4)	0.0003 (4)

Geometric parameters (Å, º) top

S1—C11	1.6869 (12)	C5—C6	1.3954 (18)
O1—C1	1.4145 (16)	C6—C7	1.3927 (18)
O1—C9	1.4331 (16)	C7—C8	1.5072 (17)
O2—C8	1.4280 (15)	C1—H1	0.972 (17)
O2—C10	1.4204 (18)	C3—H3	0.9500
N1—C1	1.4705 (15)	C4—H4	0.9500
N1—C8	1.4571 (17)	C5—H5	0.9500
N1—C11	1.3653 (16)	C6—H6	0.9500
N2—C11	1.3300 (17)	C8—H8	0.979 (16)
N2—H1N	0.891 (17)	C9—H9A	0.9800
N2—H2N	0.826 (17)	C9—H9B	0.9800
C1—C2	1.5062 (18)	C9—H9C	0.9800
C2—C7	1.3887 (17)	C10—H10A	0.9800
C2—C3	1.3905 (17)	C10—H10B	0.9800
C3—C4	1.3946 (19)	C10—H10C	0.9800
C4—C5	1.3942 (19)

S1···O2	3.3984 (10)	C6···H10A	2.9600
S1···N2ⁱ	3.2857 (11)	C6···H1^vi	2.819 (17)
S1···H3ⁱⁱ	2.7900	C6···H9B^iv	2.8400
S1···H8	2.697 (16)	C7···H1^vi	2.773 (17)
S1···H2Nⁱ	2.646 (17)	C7···H10A	3.0100
O1···N2	2.9867 (14)	C10···H10B^v	2.8900
O1···N2ⁱⁱⁱ	2.9738 (14)	C10···H5^vii	2.9800
O2···S1	3.3984 (10)	H1···N2	2.637 (16)
O1···H1Nⁱⁱⁱ	2.087 (17)	H1···H2N	2.28 (2)
O1···H2N	2.413 (17)	H1···C2^vi	2.800 (18)
O2···H9C	2.7500	H1···C3^vi	2.920 (17)
O2···H9A^iv	2.7000	H1···C4^vi	2.955 (16)
O2···H10B^v	2.8200	H1···C5^vi	2.897 (17)
N2···C6^vi	3.3938 (16)	H1···C6^vi	2.819 (17)
N2···O1	2.9867 (14)	H1···C7^vi	2.773 (17)
N2···O1ⁱ	2.9738 (14)	H1N···O1ⁱ	2.087 (17)
N2···S1ⁱⁱⁱ	3.2857 (11)	H1N···C1ⁱ	2.986 (17)
N1···H9C	2.6000	H2N···O1	2.413 (17)
N2···H1	2.637 (16)	H2N···C1	2.488 (17)
C1···C2^vi	3.4582 (18)	H2N···H1	2.28 (2)
C1···C7^vi	3.5200 (17)	H2N···S1ⁱⁱⁱ	2.646 (17)
C2···C2^vi	3.4486 (17)	H3···S1^viii	2.7900
C2···C1^vi	3.4582 (18)	H5···C10^vii	2.9800
C3···C3^vi	3.4413 (17)	H6···H10A	2.4400
C6···N2^vi	3.3938 (16)	H6···H10A^vii	2.5200
C6···C9^iv	3.4352 (19)	H8···S1	2.697 (16)
C6···C10	3.563 (2)	H8···H10C	2.2800
C7···C1^vi	3.5200 (17)	H9A···C2	2.7200
C7···C9^iv	3.5571 (19)	H9A···O2^iv	2.7000
C9···C7^iv	3.5571 (19)	H9B···C6^iv	2.8400
C9···C6^iv	3.4352 (19)	H9C···O2	2.7500
C10···C10^v	3.438 (2)	H9C···N1	2.6000
C10···C6	3.563 (2)	H10A···C6	2.9600
C1···H1Nⁱⁱⁱ	2.986 (17)	H10A···C7	3.0100
C1···H2N	2.488 (17)	H10A···H6	2.4400
C2···H9A	2.7200	H10A···H6^vii	2.5200
C2···H1^vi	2.800 (18)	H10B···O2^v	2.8200
C3···H1^vi	2.920 (17)	H10B···C10^v	2.8900
C4···H1^vi	2.955 (16)	H10C···H8	2.2800
C5···H1^vi	2.897 (17)

C1—O1—C9	115.45 (10)	O1—C1—H1	101.4 (10)
C8—O2—C10	112.80 (10)	N1—C1—H1	109.8 (8)
C1—N1—C8	113.96 (10)	C2—C1—H1	113.8 (10)
C1—N1—C11	123.18 (10)	C2—C3—H3	121.00
C8—N1—C11	121.97 (10)	C4—C3—H3	121.00
H1N—N2—H2N	119.8 (16)	C3—C4—H4	120.00
C11—N2—H1N	117.0 (11)	C5—C4—H4	120.00
C11—N2—H2N	122.7 (12)	C4—C5—H5	120.00
O1—C1—N1	113.65 (10)	C6—C5—H5	120.00
O1—C1—C2	116.61 (10)	C5—C6—H6	121.00
N1—C1—C2	101.95 (10)	C7—C6—H6	121.00
C1—C2—C3	127.81 (11)	O2—C8—H8	111.2 (9)
C3—C2—C7	121.39 (12)	N1—C8—H8	109.6 (9)
C1—C2—C7	110.61 (10)	C7—C8—H8	113.7 (9)
C2—C3—C4	118.00 (12)	O1—C9—H9A	109.00
C3—C4—C5	120.95 (12)	O1—C9—H9B	109.00
C4—C5—C6	120.59 (13)	O1—C9—H9C	109.00
C5—C6—C7	118.48 (11)	H9A—C9—H9B	109.00
C2—C7—C6	120.56 (11)	H9A—C9—H9C	109.00
C2—C7—C8	110.63 (11)	H9B—C9—H9C	109.00
C6—C7—C8	128.80 (11)	O2—C10—H10A	109.00
N1—C8—C7	101.99 (9)	O2—C10—H10B	109.00
O2—C8—N1	108.33 (10)	O2—C10—H10C	109.00
O2—C8—C7	111.52 (10)	H10A—C10—H10B	109.00
S1—C11—N1	121.78 (10)	H10A—C10—H10C	109.00
S1—C11—N2	121.31 (10)	H10B—C10—H10C	109.00
N1—C11—N2	116.90 (11)

C9—O1—C1—N1	−62.73 (14)	N1—C1—C2—C3	−175.58 (12)
C9—O1—C1—C2	55.45 (14)	N1—C1—C2—C7	−0.62 (13)
C10—O2—C8—N1	−153.14 (10)	C1—C2—C3—C4	173.19 (12)
C10—O2—C8—C7	95.39 (12)	C7—C2—C3—C4	−1.28 (19)
C8—N1—C1—O1	120.77 (11)	C1—C2—C7—C6	−173.11 (11)
C8—N1—C1—C2	−5.57 (13)	C1—C2—C7—C8	6.27 (14)
C11—N1—C1—O1	−69.90 (15)	C3—C2—C7—C6	2.22 (19)
C11—N1—C1—C2	163.77 (11)	C3—C2—C7—C8	−178.40 (11)
C1—N1—C8—O2	−108.78 (11)	C2—C3—C4—C5	−0.45 (19)
C1—N1—C8—C7	8.96 (13)	C3—C4—C5—C6	1.3 (2)
C11—N1—C8—O2	81.74 (13)	C4—C5—C6—C7	−0.33 (19)
C11—N1—C8—C7	−160.52 (11)	C5—C6—C7—C2	−1.37 (18)
C1—N1—C11—S1	−167.45 (9)	C5—C6—C7—C8	179.37 (12)
C1—N1—C11—N2	11.57 (18)	C2—C7—C8—O2	106.35 (12)
C8—N1—C11—S1	1.05 (17)	C2—C7—C8—N1	−9.08 (13)
C8—N1—C11—N2	−179.93 (11)	C6—C7—C8—O2	−74.34 (16)
O1—C1—C2—C3	60.04 (17)	C6—C7—C8—N1	170.24 (12)
O1—C1—C2—C7	−125.00 (11)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N···O1ⁱ	0.891 (17)	2.087 (17)	2.9738 (14)	172.9 (15)
N2—H2N···O1	0.826 (17)	2.413 (17)	2.9867 (14)	127.3 (14)
N2—H2N···S1ⁱⁱⁱ	0.826 (17)	2.646 (17)	3.2857 (11)	135.4 (15)
C3—H3···S1^viii	0.9500	2.7900	3.7362 (13)	178.00
C8—H8···S1	0.979 (16)	2.697 (16)	3.0318 (12)	100.5 (11)
C9—H9C···N1	0.9800	2.6000	2.9593 (18)	102.00
C1—H1···CgB^vi	0.9800	2.500 (17)	3.4059 (13)	155.1 (1)
C9—H9C···CgA	0.9800	2.74	2.9052 (16)	90

Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (iii) −x+1/2, y−1/2, −z+1/2; (vi) −x, y, −z+1/2; (viii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₄N₂O₂S
M_r	238.30
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	15.4577 (8), 8.6455 (5), 18.2184 (10)
β (°)	107.322 (2)
V (Å³)	2324.3 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.20 × 0.16 × 0.12

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.945, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	18083, 2894, 2471
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.110, 1.01
No. of reflections	2894
No. of parameters	159
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.37

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003), 'WinGX publication routines (Farrugia, 1999) and PLATON'.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N···O1ⁱ	0.891 (17)	2.087 (17)	2.9738 (14)	172.9 (15)
N2—H2N···O1	0.826 (17)	2.413 (17)	2.9867 (14)	127.3 (14)
N2—H2N···S1ⁱⁱ	0.826 (17)	2.646 (17)	3.2857 (11)	135.4 (15)
C3—H3···S1ⁱⁱⁱ	0.9500	2.7900	3.7362 (13)	178.00
C8—H8···S1	0.979 (16)	2.697 (16)	3.0318 (12)	100.5 (11)
C9—H9C···N1	0.9800	2.6000	2.9593 (18)	102.00
C1—H1···CgB^iv	0.9800	2.500 (17)	3.4059 (13)	155.1 (1)
C9—H9C···CgA	0.9800	2.74	2.9052 (16)	90

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

References

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