3-(3-Amino-phenyl-sulfon-yl)aniline.

In the title compound, C(12)H(12)N(2)O(2)S, the aromatic rings are oriented at a dihedral angle of 79.48 (4)°. Intra-molecular C-H⋯O hydrogen bonds result in the formation of two five-membered rings with envelope conformations. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules. π-π Contacts between the benzene rings, [centroid-centroid distance = 4.211 (3) Å] may further stabilize the structure.

Related literature

For general background, see: Block (1992 ▶); Holland (1988 ▶); McMohan et al. (1993 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C12H12N2O2S

M = 248.30

Monoclinic,

a = 8.6282 (17) Å

b = 8.8017 (18) Å

c = 16.052 (3) Å

β = 98.12 (3)°

V = 1206.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 298 (2) K

0.40 × 0.30 × 0.28 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.910, T max = 0.933

18754 measured reflections

4145 independent reflections

2971 reflections with I > 2σ(I)

R int = 0.091

Refinement

R[F 2 > 2σ(F 2)] = 0.078

wR(F 2) = 0.218

S = 1.12

4145 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.64 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808043389/hk2599sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808043389/hk2599Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H12N2O2S	F(000) = 520
Mr = 248.30	Dx = 1.367 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1532 reflections
a = 8.6282 (17) Å	θ = 2.4–32.0°
b = 8.8017 (18) Å	µ = 0.26 mm−1
c = 16.052 (3) Å	T = 298 K
β = 98.12 (3)°	Colorless, yellow
V = 1206.8 (4) Å3	0.40 × 0.30 × 0.28 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	4145 independent reflections
Radiation source: fine-focus sealed tube	2971 reflections with I > 2σ(I)
graphite	Rint = 0.091
φ and ω scans	θmax = 32.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −12→12
Tmin = 0.910, Tmax = 0.933	k = −12→13
18754 measured reflections	l = −23→23

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)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.218	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0789P)2 + 0.6213P] where P = (Fo2 + 2Fc2)/3
4145 reflections	(Δ/σ)max = 0.003
154 parameters	Δρmax = 0.64 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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	0.25722 (7)	0.35241 (8)	0.12847 (4)	0.0538 (2)
O1	0.2448 (2)	0.4691 (2)	0.06463 (15)	0.0705 (6)
O2	0.3825 (2)	0.3662 (3)	0.19740 (15)	0.0734 (6)
N1	0.4728 (5)	−0.1878 (5)	0.1176 (3)	0.1187 (14)
H1A	0.4757	−0.2745	0.0933	0.142*
H1B	0.5288	−0.1722	0.1656	0.142*
N2	−0.3243 (3)	0.4789 (4)	0.1136 (2)	0.0844 (9)
H2B	−0.4113	0.4778	0.1340	0.101*
H2A	−0.3183	0.5252	0.0670	0.101*
C1	0.3714 (3)	0.0656 (3)	0.11930 (19)	0.0633 (7)
H1	0.4308	0.0854	0.1711	0.076*
C2	0.3800 (4)	−0.0758 (4)	0.0805 (2)	0.0765 (9)
C3	0.2912 (6)	−0.1002 (5)	0.0046 (3)	0.0977 (13)
H3	0.2966	−0.1946	−0.0208	0.117*
C4	0.1948 (6)	0.0077 (5)	−0.0357 (3)	0.0979 (13)
H4	0.1368	−0.0127	−0.0879	0.117*
C5	0.1844 (5)	0.1493 (4)	0.0026 (2)	0.0785 (9)
H5	0.1187	0.2244	−0.0234	0.094*
C6	0.2733 (3)	0.1754 (3)	0.07936 (18)	0.0558 (6)
C7	0.0781 (3)	0.3441 (3)	0.16923 (16)	0.0498 (5)
C8	−0.0511 (3)	0.4117 (3)	0.12433 (16)	0.0513 (5)
H8	−0.0433	0.4605	0.0737	0.062*
C9	−0.1947 (3)	0.4063 (3)	0.15552 (18)	0.0545 (6)
C10	−0.2009 (4)	0.3306 (4)	0.2309 (2)	0.0645 (7)
H10	−0.2956	0.3251	0.2522	0.077*
C11	−0.0704 (4)	0.2637 (4)	0.2746 (2)	0.0735 (8)
H11	−0.0780	0.2140	0.3250	0.088*
C12	0.0725 (4)	0.2692 (4)	0.24466 (19)	0.0660 (7)
H12	0.1613	0.2242	0.2741	0.079*

	U11	U22	U33	U12	U13	U23
S1	0.0398 (3)	0.0559 (4)	0.0663 (4)	−0.0023 (2)	0.0092 (2)	0.0031 (3)
O1	0.0610 (12)	0.0647 (12)	0.0897 (15)	−0.0026 (9)	0.0239 (11)	0.0198 (11)
O2	0.0473 (10)	0.0876 (15)	0.0821 (14)	−0.0077 (10)	−0.0019 (10)	−0.0096 (12)
N1	0.136 (3)	0.095 (2)	0.130 (3)	0.045 (2)	0.036 (3)	−0.002 (2)
N2	0.0493 (13)	0.108 (2)	0.101 (2)	0.0197 (14)	0.0271 (14)	0.0260 (18)
C1	0.0570 (15)	0.0685 (17)	0.0684 (17)	0.0104 (12)	0.0225 (13)	0.0047 (14)
C2	0.084 (2)	0.0656 (18)	0.088 (2)	0.0161 (16)	0.0439 (19)	0.0042 (16)
C3	0.135 (4)	0.079 (2)	0.089 (3)	−0.002 (2)	0.050 (3)	−0.020 (2)
C4	0.124 (4)	0.091 (3)	0.079 (2)	−0.004 (3)	0.018 (2)	−0.013 (2)
C5	0.083 (2)	0.082 (2)	0.0693 (19)	0.0001 (18)	0.0068 (17)	−0.0018 (17)
C6	0.0501 (12)	0.0577 (14)	0.0627 (15)	0.0024 (10)	0.0182 (11)	0.0013 (11)
C7	0.0449 (11)	0.0504 (12)	0.0552 (13)	−0.0016 (9)	0.0105 (10)	−0.0026 (10)
C8	0.0450 (11)	0.0535 (13)	0.0572 (13)	0.0022 (10)	0.0131 (10)	0.0021 (11)
C9	0.0466 (12)	0.0540 (13)	0.0652 (15)	0.0025 (10)	0.0155 (11)	−0.0061 (11)
C10	0.0601 (15)	0.0708 (18)	0.0678 (17)	−0.0050 (13)	0.0272 (13)	−0.0045 (13)
C11	0.0748 (19)	0.087 (2)	0.0623 (17)	−0.0027 (16)	0.0236 (15)	0.0147 (16)
C12	0.0609 (16)	0.0750 (19)	0.0623 (16)	0.0042 (14)	0.0097 (13)	0.0128 (14)

O1—S1	1.444 (2)	C5—C6	1.376 (5)
O2—S1	1.439 (2)	C5—H5	0.9300
N1—H1A	0.8600	C6—S1	1.760 (3)
N1—H1B	0.8600	C7—C8	1.375 (4)
N2—H2B	0.8600	C7—C12	1.386 (4)
N2—H2A	0.8600	C7—S1	1.763 (2)
C1—C6	1.382 (4)	C8—C9	1.401 (3)
C1—C2	1.398 (4)	C8—H8	0.9300
C1—H1	0.9300	C9—N2	1.378 (4)
C2—N1	1.353 (5)	C9—C10	1.390 (4)
C2—C3	1.361 (6)	C10—C11	1.372 (5)
C3—C4	1.365 (6)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.386 (4)
C4—C5	1.398 (5)	C11—H11	0.9300
C4—H4	0.9300	C12—H12	0.9300
O1—S1—C6	108.32 (13)	C6—C5—C4	118.7 (4)
O1—S1—C7	108.16 (12)	C6—C5—H5	120.6
O2—S1—O1	117.27 (14)	C4—C5—H5	120.6
O2—S1—C6	108.72 (14)	C5—C6—C1	121.7 (3)
O2—S1—C7	108.72 (13)	C5—C6—S1	118.7 (2)
C6—S1—C7	104.97 (12)	C1—C6—S1	119.6 (2)
C2—N1—H1A	120.0	C8—C7—C12	122.6 (2)
C2—N1—H1B	120.0	C8—C7—S1	118.43 (19)
H1A—N1—H1B	120.0	C12—C7—S1	119.0 (2)
C9—N2—H2A	120.0	C7—C8—C9	119.4 (2)
C9—N2—H2B	120.0	C7—C8—H8	120.3
H2B—N2—H2A	120.0	C9—C8—H8	120.3
C6—C1—C2	119.0 (3)	N2—C9—C10	121.3 (2)
C6—C1—H1	120.5	N2—C9—C8	120.5 (3)
C2—C1—H1	120.5	C10—C9—C8	118.2 (3)
N1—C2—C3	120.1 (4)	C11—C10—C9	121.4 (3)
N1—C2—C1	121.2 (4)	C11—C10—H10	119.3
C3—C2—C1	118.7 (3)	C9—C10—H10	119.3
C2—C3—C4	122.9 (4)	C10—C11—C12	120.9 (3)
C2—C3—H3	118.5	C10—C11—H11	119.5
C4—C3—H3	118.5	C12—C11—H11	119.5
C3—C4—C5	119.0 (4)	C7—C12—C11	117.5 (3)
C3—C4—H4	120.5	C7—C12—H12	121.2
C5—C4—H4	120.5	C11—C12—H12	121.2
C6—C1—C2—N1	−179.1 (3)	C9—C10—C11—C12	−0.2 (5)
C6—C1—C2—C3	0.0 (4)	C8—C7—C12—C11	0.0 (5)
N1—C2—C3—C4	179.6 (4)	S1—C7—C12—C11	−179.5 (2)
C1—C2—C3—C4	0.4 (6)	C10—C11—C12—C7	−0.1 (5)
C2—C3—C4—C5	−0.8 (7)	C5—C6—S1—O2	−167.8 (2)
C3—C4—C5—C6	0.6 (6)	C1—C6—S1—O2	13.6 (3)
C4—C5—C6—C1	−0.2 (5)	C5—C6—S1—O1	−39.4 (3)
C4—C5—C6—S1	−178.7 (3)	C1—C6—S1—O1	142.1 (2)
C2—C1—C6—C5	−0.1 (4)	C5—C6—S1—C7	76.0 (3)
C2—C1—C6—S1	178.4 (2)	C1—C6—S1—C7	−102.6 (2)
C12—C7—C8—C9	0.4 (4)	C8—C7—S1—O2	144.7 (2)
S1—C7—C8—C9	179.9 (2)	C12—C7—S1—O2	−35.7 (3)
C7—C8—C9—N2	177.2 (3)	C8—C7—S1—O1	16.4 (3)
C7—C8—C9—C10	−0.7 (4)	C12—C7—S1—O1	−164.1 (2)
N2—C9—C10—C11	−177.2 (3)	C8—C7—S1—C6	−99.1 (2)
C8—C9—C10—C11	0.6 (5)	C12—C7—S1—C6	80.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2i	0.86	2.25	3.091 (5)	166
N2—H2A···O1ii	0.86	2.29	3.069 (4)	151
N2—H2B···O2iii	0.86	2.38	3.187 (4)	156
C1—H1···O2	0.93	2.55	2.924 (4)	104
C8—H8···O1	0.93	2.51	2.895 (3)	105

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O2i	0.86	2.25	3.091 (5)	166
N2—H2A⋯O1ii	0.86	2.29	3.069 (4)	151
N2—H2B⋯O2iii	0.86	2.38	3.187 (4)	156
C1—H1⋯O2	0.93	2.55	2.924 (4)	104
C8—H8⋯O1	0.93	2.51	2.895 (3)	105

Symmetry codes: (i) ; (ii) ; (iii) .