4-(2,3-Di-hydro-thieno[3,4-b][1,4]dioxin-5-yl)aniline.

In the title mol-ecule, C12H11NO2S, the dioxane-type ring adopts a half-chair conformation. The thio-phene ring forms a dihedral angle of 12.53 (6)° with the benzene ring. In the crystal, N-H⋯O, hydrogen bonds link mol-ecules, forming chains along the c-axis direction. A weak intra-molecular C-H⋯O hydrogen bond is observed.

Related literature

For related structures, see: Chen et al. (2011 ▶); Riehn et al. (2000 ▶); Sotzing & Reynolds (1996 ▶). For the properties of 4-(2,3-di­hydro­thieno[3,4-b][1,4]dioxin-5-yl)aniline see: Trippé-Allard & Lacroix (2013 ▶).

Experimental

Crystal data

C12H11NO2S

M = 233.28

Orthorhombic,

a = 6.9117 (6) Å

b = 7.0898 (6) Å

c = 21.4784 (16) Å

V = 1052.50 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 100 K

0.29 × 0.27 × 0.08 mm

Data collection

Rigaku Saturn724+ diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 2001 ▶) T min = 0.858, T max = 1.000

11854 measured reflections

1853 independent reflections

1812 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.075

S = 0.86

1853 reflections

153 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 743 Friedel pairs

Absolute structure parameter: 0.03 (8)

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) within WinGX (Farrugia, 2012 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶), POV-RAY (Cason, 2004 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814014093/lh5708sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814014093/lh5708Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814014093/lh5708Isup3.cml

CCDC reference: 1008614

Additional supporting information: crystallographic information; 3D view; checkCIF report

C12H11NO2S	F(000) = 488
Mr = 233.28	Dx = 1.472 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2964 reflections
a = 6.9117 (6) Å	θ = 2.9–28.2°
b = 7.0898 (6) Å	µ = 0.29 mm−1
c = 21.4784 (16) Å	T = 100 K
V = 1052.50 (15) Å3	Plate, orange
Z = 4	0.29 × 0.27 × 0.08 mm

Rigaku Saturn724+ diffractometer	1853 independent reflections
Radiation source: fine-focus sealed tube	1812 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 28.5714 pixels mm-1	θmax = 25.0°, θmin = 3.0°
profile data from ω scans	h = −8→8
Absorption correction: multi-scan (ABSCOR; Higashi, 2001)	k = −8→8
Tmin = 0.858, Tmax = 1.000	l = −22→25
11854 measured reflections

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) = 0.075	w = 1/[σ2(Fo2) + (0.0543P)2 + 0.6318P] where P = (Fo2 + 2Fc2)/3
S = 0.86	(Δ/σ)max = 0.001
1853 reflections	Δρmax = 0.43 e Å−3
153 parameters	Δρmin = −0.21 e Å−3
0 restraints	Absolute structure: Flack (1983), 743 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (8)

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.

	x	y	z	Uiso*/Ueq
S1	0.53914 (6)	0.63412 (6)	0.83637 (2)	0.02511 (15)
O1	0.73741 (18)	0.56761 (18)	0.66914 (6)	0.0229 (3)
O2	1.02695 (18)	0.47874 (17)	0.76297 (6)	0.0203 (3)
N1	1.1401 (3)	0.4133 (3)	1.07137 (9)	0.0332 (4)
C1	0.5329 (3)	0.6408 (3)	0.75642 (9)	0.0257 (4)
H1	0.4267	0.6801	0.7332	0.031*
C2	0.7019 (3)	0.5818 (2)	0.73164 (9)	0.0199 (4)
C3	0.9069 (3)	0.4540 (3)	0.65674 (9)	0.0238 (4)
H3A	0.9447	0.4687	0.6135	0.029*
H3B	0.8767	0.3220	0.6638	0.029*
C4	1.0715 (3)	0.5118 (3)	0.69824 (8)	0.0207 (4)
H4A	1.1865	0.4411	0.6870	0.025*
H4B	1.0988	0.6447	0.6921	0.025*
C5	0.8432 (2)	0.5355 (2)	0.77795 (8)	0.0182 (4)
C6	0.7780 (2)	0.5557 (2)	0.83812 (9)	0.0196 (4)
C7	0.8775 (3)	0.5263 (2)	0.89751 (9)	0.0199 (4)
C8	1.0548 (3)	0.4311 (2)	0.90137 (9)	0.0225 (4)
H8	1.1154	0.3915	0.8650	0.027*
C9	1.1417 (3)	0.3948 (3)	0.95825 (9)	0.0262 (4)
H9	1.2593	0.3312	0.9595	0.031*
C10	1.0543 (3)	0.4530 (3)	1.01393 (9)	0.0250 (4)
C11	0.8850 (3)	0.5570 (3)	1.01015 (9)	0.0266 (4)
H11	0.8296	0.6041	1.0464	0.032*
C12	0.7970 (3)	0.5920 (3)	0.95357 (9)	0.0257 (4)
H12	0.6823	0.6605	0.9526	0.031*
H10A	1.065 (4)	0.415 (3)	1.1041 (11)	0.035 (6)*
H10B	1.215 (4)	0.315 (4)	1.0685 (12)	0.042 (7)*

	U11	U22	U33	U12	U13	U23
S1	0.0134 (2)	0.0283 (3)	0.0336 (3)	0.0022 (2)	0.0016 (2)	−0.0034 (2)
O1	0.0188 (6)	0.0237 (6)	0.0262 (7)	0.0012 (5)	−0.0045 (6)	−0.0017 (5)
O2	0.0152 (6)	0.0226 (6)	0.0230 (6)	0.0032 (6)	0.0014 (5)	0.0021 (5)
N1	0.0385 (11)	0.0316 (10)	0.0295 (11)	0.0059 (9)	−0.0036 (9)	0.0010 (8)
C1	0.0154 (8)	0.0235 (8)	0.0382 (11)	0.0007 (9)	−0.0046 (8)	−0.0025 (8)
C2	0.0185 (9)	0.0146 (8)	0.0264 (10)	−0.0029 (7)	−0.0037 (7)	0.0002 (7)
C3	0.0210 (9)	0.0215 (9)	0.0289 (10)	0.0005 (8)	0.0002 (7)	−0.0030 (8)
C4	0.0191 (9)	0.0185 (8)	0.0245 (10)	0.0006 (7)	0.0026 (8)	0.0001 (7)
C5	0.0123 (8)	0.0121 (8)	0.0302 (10)	−0.0009 (7)	−0.0002 (7)	−0.0007 (7)
C6	0.0121 (8)	0.0146 (8)	0.0322 (10)	−0.0004 (7)	0.0012 (8)	0.0009 (8)
C7	0.0181 (9)	0.0144 (8)	0.0271 (10)	−0.0032 (7)	0.0029 (7)	0.0014 (7)
C8	0.0225 (9)	0.0204 (8)	0.0244 (9)	0.0030 (8)	0.0000 (8)	−0.0019 (7)
C9	0.0233 (9)	0.0226 (9)	0.0327 (11)	0.0053 (8)	−0.0040 (8)	−0.0028 (8)
C10	0.0284 (10)	0.0202 (8)	0.0264 (10)	−0.0053 (9)	−0.0015 (8)	0.0030 (8)
C11	0.0263 (10)	0.0288 (10)	0.0247 (10)	−0.0014 (9)	0.0074 (8)	−0.0011 (8)
C12	0.0202 (9)	0.0243 (9)	0.0327 (11)	0.0022 (8)	0.0048 (8)	0.0027 (8)

S1—C1	1.718 (2)	C4—H4A	0.9700
S1—C6	1.7424 (18)	C4—H4B	0.9700
O1—C2	1.368 (2)	C5—C6	1.376 (3)
O1—C3	1.446 (2)	C6—C7	1.464 (3)
O2—C5	1.370 (2)	C7—C8	1.402 (3)
O2—C4	1.443 (2)	C7—C12	1.406 (3)
N1—C10	1.397 (3)	C8—C9	1.385 (3)
N1—H10A	0.87 (3)	C8—H8	0.9300
N1—H10B	0.87 (3)	C9—C10	1.402 (3)
C1—C2	1.350 (3)	C9—H9	0.9300
C1—H1	0.9300	C10—C11	1.385 (3)
C2—C5	1.432 (3)	C11—C12	1.382 (3)
C3—C4	1.503 (3)	C11—H11	0.9300
C3—H3A	0.9700	C12—H12	0.9300
C3—H3B	0.9700
C1—S1—C6	93.10 (9)	O2—C5—C6	123.69 (16)
C2—O1—C3	111.52 (14)	O2—C5—C2	122.42 (16)
C5—O2—C4	112.11 (13)	C6—C5—C2	113.89 (16)
C10—N1—H10A	117.2 (17)	C5—C6—C7	130.51 (16)
C10—N1—H10B	110.5 (17)	C5—C6—S1	108.87 (14)
H10A—N1—H10B	115 (2)	C7—C6—S1	120.60 (14)
C2—C1—S1	111.33 (15)	C8—C7—C12	117.05 (17)
C2—C1—H1	124.3	C8—C7—C6	122.06 (16)
S1—C1—H1	124.3	C12—C7—C6	120.89 (17)
C1—C2—O1	124.39 (17)	C9—C8—C7	121.37 (18)
C1—C2—C5	112.78 (17)	C9—C8—H8	119.3
O1—C2—C5	122.83 (16)	C7—C8—H8	119.3
O1—C3—C4	110.61 (14)	C8—C9—C10	120.74 (18)
O1—C3—H3A	109.5	C8—C9—H9	119.6
C4—C3—H3A	109.5	C10—C9—H9	119.6
O1—C3—H3B	109.5	C11—C10—N1	121.13 (19)
C4—C3—H3B	109.5	C11—C10—C9	118.06 (18)
H3A—C3—H3B	108.1	N1—C10—C9	120.76 (19)
O2—C4—C3	111.42 (15)	C12—C11—C10	121.27 (18)
O2—C4—H4A	109.3	C12—C11—H11	119.4
C3—C4—H4A	109.3	C10—C11—H11	119.4
O2—C4—H4B	109.3	C11—C12—C7	121.31 (18)
C3—C4—H4B	109.3	C11—C12—H12	119.3
H4A—C4—H4B	108.0	C7—C12—H12	119.3
C6—S1—C1—C2	1.54 (14)	C2—C5—C6—S1	−0.29 (19)
S1—C1—C2—O1	178.30 (13)	C1—S1—C6—C5	−0.68 (13)
S1—C1—C2—C5	−2.0 (2)	C1—S1—C6—C7	177.95 (14)
C3—O1—C2—C1	−164.18 (17)	C5—C6—C7—C8	−13.8 (3)
C3—O1—C2—C5	16.1 (2)	S1—C6—C7—C8	167.89 (14)
C2—O1—C3—C4	−46.87 (19)	C5—C6—C7—C12	166.69 (19)
C5—O2—C4—C3	−44.06 (19)	S1—C6—C7—C12	−11.6 (2)
O1—C3—C4—O2	63.54 (19)	C12—C7—C8—C9	3.3 (3)
C4—O2—C5—C6	−166.28 (16)	C6—C7—C8—C9	−176.21 (18)
C4—O2—C5—C2	12.9 (2)	C7—C8—C9—C10	−0.1 (3)
C1—C2—C5—O2	−177.73 (15)	C8—C9—C10—C11	−3.7 (3)
O1—C2—C5—O2	2.0 (3)	C8—C9—C10—N1	178.79 (19)
C1—C2—C5—C6	1.5 (2)	N1—C10—C11—C12	−178.21 (19)
O1—C2—C5—C6	−178.78 (15)	C9—C10—C11—C12	4.3 (3)
O2—C5—C6—C7	0.5 (3)	C10—C11—C12—C7	−1.1 (3)
C2—C5—C6—C7	−178.74 (17)	C8—C7—C12—C11	−2.7 (3)
O2—C5—C6—S1	178.91 (13)	C6—C7—C12—C11	176.79 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H10A···O1i	0.88 (3)	2.52 (3)	3.352 (2)	160 (2)
C8—H8···O2	0.93	2.36	2.998 (2)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H10A⋯O1i	0.88 (3)	2.52 (3)	3.352 (2)	160 (2)
C8—H8⋯O2	0.93	2.36	2.998 (2)	126

Symmetry code: (i) .