Bis(3-amino-phen-yl) sulfone acetonitrile solvate.

In the sulfone mol-ecule of the title compound, C(12)H(12)N(2)O(2)S·C(2)H(3)N, the two benzene rings are oriented at a dihedral angle of 80.69 (3)°. Weak intra-molecular C-H⋯O hydrogen bonds result in the formation of two five-membered rings, which both have envelope conformations. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules.

Related literature

For related literature, see: Yang et al. (2003 ▶); Rudyk et al. (2003 ▶); Ayyangar et al. (1981 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C12H12N2O2S·C2H3N

M = 289.35

Orthorhombic,

a = 9.1690 (18) Å

b = 15.559 (3) Å

c = 20.960 (4) Å

V = 2990.2 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.22 mm−1

T = 294 (2) K

0.40 × 0.30 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.917, T max = 0.937

2674 measured reflections

2674 independent reflections

1644 reflections with I > 2σ(I)

3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.135

S = 1.03

2674 reflections

175 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808014840/hk2464sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014840/hk2464Isup2.hkl

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

C12H12N2O2S·C2H3N	F000 = 1216
Mr = 289.35	Dx = 1.285 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 9.1690 (18) Å	θ = 10–13º
b = 15.559 (3) Å	µ = 0.22 mm−1
c = 20.960 (4) Å	T = 294 (2) K
V = 2990.2 (10) Å3	Block, light yellow
Z = 8	0.40 × 0.30 × 0.30 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.0000
Radiation source: fine-focus sealed tube	θmax = 25.1º
Monochromator: graphite	θmin = 1.9º
T = 294(2) K	h = 0→10
ω/2θ scans	k = 0→18
Absorption correction: ψ scan(North et al., 1968)	l = 0→24
Tmin = 0.917, Tmax = 0.937	3 standard reflections
2674 measured reflections	every 120 min
2674 independent reflections	intensity decay: none
1644 reflections with I > 2σ(I)

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)] = 0.055	H-atom parameters constrained
wR(F2) = 0.135	w = 1/[σ2(Fo2) + (0.05P)2 + 2P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2674 reflections	Δρmax = 0.36 e Å−3
175 parameters	Δρmin = −0.23 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 > 2sigma(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
S	0.45811 (9)	0.20077 (5)	0.17605 (4)	0.0493 (3)
O1	0.5131 (3)	0.23557 (15)	0.23465 (12)	0.0692 (8)
O2	0.3393 (3)	0.24395 (14)	0.14448 (13)	0.0662 (7)
N1	0.9991 (3)	0.2160 (3)	0.11603 (18)	0.0941 (13)
H1B	1.0185	0.2305	0.1547	0.113*
H1C	1.0683	0.2116	0.0885	0.113*
N2	0.1514 (3)	−0.06128 (19)	0.11889 (14)	0.0639 (9)
H2B	0.1248	−0.1138	0.1240	0.077*
H2C	0.1096	−0.0298	0.0905	0.077*
N3	0.8308 (6)	−0.0861 (3)	0.0059 (2)	0.125
C1	0.8592 (4)	0.2000 (2)	0.09841 (18)	0.0560 (9)
C2	0.8255 (5)	0.1794 (2)	0.03521 (19)	0.0657 (11)
H2D	0.9005	0.1746	0.0056	0.079*
C3	0.6825 (5)	0.1660 (3)	0.01564 (19)	0.0690 (11)
H3A	0.6633	0.1513	−0.0266	0.083*
C4	0.5695 (4)	0.1741 (2)	0.05805 (17)	0.0582 (10)
H4A	0.4734	0.1665	0.0450	0.070*
C5	0.6022 (3)	0.19405 (19)	0.12110 (15)	0.0428 (8)
C6	0.7437 (4)	0.2064 (2)	0.14153 (16)	0.0502 (8)
H6A	0.7622	0.2189	0.1841	0.060*
C7	0.2607 (4)	−0.0275 (2)	0.15608 (15)	0.0454 (8)
C8	0.3005 (3)	0.05871 (19)	0.14943 (15)	0.0434 (8)
H8A	0.2563	0.0927	0.1185	0.052*
C9	0.4056 (3)	0.09322 (19)	0.18883 (15)	0.0431 (8)
C10	0.4737 (4)	0.0444 (2)	0.23542 (17)	0.0582 (10)
H10A	0.5433	0.0685	0.2623	0.070*
C11	0.4356 (4)	−0.0407 (2)	0.24077 (19)	0.0650 (11)
H11A	0.4818	−0.0749	0.2711	0.078*
C12	0.3309 (4)	−0.0763 (2)	0.20243 (17)	0.0563 (9)
H12A	0.3064	−0.1339	0.2074	0.068*
C13	0.6947 (7)	−0.0534 (4)	0.1078 (2)	0.130 (2)
H13A	0.6632	−0.1062	0.1270	0.195*
H13B	0.6113	−0.0182	0.0986	0.195*
H13C	0.7580	−0.0234	0.1368	0.195*
C14	0.7706 (5)	−0.0714 (3)	0.0506 (2)	0.0858 (14)

	U11	U22	U33	U12	U13	U23
S	0.0474 (5)	0.0365 (4)	0.0641 (6)	−0.0012 (4)	0.0097 (5)	−0.0078 (4)
O1	0.0785 (18)	0.0611 (15)	0.0680 (17)	−0.0187 (14)	0.0159 (15)	−0.0280 (13)
O2	0.0520 (14)	0.0409 (13)	0.106 (2)	0.0105 (12)	0.0076 (15)	0.0041 (13)
N1	0.0447 (19)	0.153 (4)	0.085 (3)	−0.007 (2)	0.0034 (18)	0.003 (2)
N2	0.075 (2)	0.0524 (17)	0.064 (2)	−0.0164 (16)	−0.0116 (18)	0.0000 (15)
N3	0.125	0.125	0.125	0.000	0.000	0.000
C1	0.045 (2)	0.060 (2)	0.063 (2)	0.0023 (19)	0.0006 (18)	0.0063 (19)
C2	0.064 (3)	0.073 (3)	0.060 (3)	0.006 (2)	0.019 (2)	0.003 (2)
C3	0.072 (3)	0.088 (3)	0.046 (2)	−0.002 (2)	0.002 (2)	−0.004 (2)
C4	0.051 (2)	0.069 (2)	0.054 (2)	−0.0041 (19)	−0.0050 (19)	−0.0003 (18)
C5	0.0463 (18)	0.0338 (16)	0.048 (2)	−0.0005 (15)	0.0029 (16)	0.0007 (15)
C6	0.0490 (19)	0.0523 (19)	0.049 (2)	−0.0045 (18)	−0.0020 (18)	−0.0006 (17)
C7	0.0461 (19)	0.0424 (18)	0.048 (2)	−0.0019 (16)	0.0052 (17)	−0.0044 (15)
C8	0.0448 (19)	0.0408 (17)	0.0447 (18)	0.0043 (15)	0.0052 (16)	0.0023 (15)
C9	0.0413 (18)	0.0376 (17)	0.050 (2)	0.0034 (14)	0.0030 (16)	−0.0015 (15)
C10	0.059 (2)	0.053 (2)	0.063 (2)	−0.0074 (18)	−0.013 (2)	0.0013 (18)
C11	0.070 (3)	0.055 (2)	0.069 (2)	−0.005 (2)	−0.021 (2)	0.0174 (19)
C12	0.064 (2)	0.0436 (19)	0.061 (2)	−0.0034 (19)	0.002 (2)	0.0042 (17)
C13	0.182 (7)	0.111 (4)	0.097 (4)	0.030 (4)	0.051 (4)	−0.002 (3)
C14	0.092 (4)	0.087 (3)	0.078 (3)	0.013 (3)	−0.002 (3)	0.004 (3)

S—O1	1.434 (2)	C5—C6	1.380 (4)
S—O2	1.441 (2)	C6—H6A	0.9300
S—C5	1.756 (3)	C7—C12	1.390 (5)
S—C9	1.762 (3)	C7—C8	1.398 (4)
C1—N1	1.358 (5)	C8—C9	1.378 (4)
C1—C6	1.396 (5)	C8—H8A	0.9300
C1—C2	1.397 (5)	C9—C10	1.386 (4)
N1—H1B	0.8600	C10—C11	1.375 (5)
N1—H1C	0.8600	C10—H10A	0.9300
N2—C7	1.374 (4)	C11—C12	1.368 (5)
N2—H2B	0.8600	C11—H11A	0.9300
N2—H2C	0.8600	C12—H12A	0.9300
C2—C3	1.390 (5)	C13—C14	1.415 (6)
C2—H2D	0.9300	C13—H13A	0.9600
C3—C4	1.371 (5)	C13—H13B	0.9600
C3—H3A	0.9300	C13—H13C	0.9600
C4—C5	1.390 (5)	C14—N3	1.111 (6)
C4—H4A	0.9300
O1—S—O2	118.90 (16)	C5—C6—H6A	119.9
O1—S—C5	108.65 (16)	C1—C6—H6A	119.9
O2—S—C5	107.18 (15)	N2—C7—C12	121.7 (3)
O1—S—C9	108.95 (15)	N2—C7—C8	120.1 (3)
O2—S—C9	107.82 (15)	C12—C7—C8	118.2 (3)
C5—S—C9	104.40 (14)	C9—C8—C7	119.8 (3)
N1—C1—C6	121.8 (3)	C9—C8—H8A	120.1
N1—C1—C2	120.6 (4)	C7—C8—H8A	120.1
C6—C1—C2	117.6 (3)	C8—C9—C10	121.6 (3)
C1—N1—H1B	120.0	C8—C9—S	118.1 (2)
C1—N1—H1C	120.0	C10—C9—S	120.3 (3)
H1B—N1—H1C	120.0	C11—C10—C9	118.1 (3)
C7—N2—H2B	120.0	C11—C10—H10A	121.0
C7—N2—H2C	120.0	C9—C10—H10A	121.0
H2B—N2—H2C	120.0	C12—C11—C10	121.3 (3)
C3—C2—C1	121.5 (4)	C12—C11—H11A	119.3
C3—C2—H2D	119.2	C10—C11—H11A	119.3
C1—C2—H2D	119.2	C11—C12—C7	121.0 (3)
C4—C3—C2	120.5 (4)	C11—C12—H12A	119.5
C4—C3—H3A	119.7	C7—C12—H12A	119.5
C2—C3—H3A	119.7	C14—C13—H13A	109.5
C3—C4—C5	118.3 (3)	C14—C13—H13B	109.5
C3—C4—H4A	120.9	H13A—C13—H13B	109.5
C5—C4—H4A	120.9	C14—C13—H13C	109.5
C6—C5—C4	121.9 (3)	H13A—C13—H13C	109.5
C6—C5—S	119.7 (3)	H13B—C13—H13C	109.5
C4—C5—S	118.3 (3)	N3—C14—C13	179.4 (6)
C5—C6—C1	120.2 (3)
N1—C1—C2—C3	−177.5 (4)	N2—C7—C8—C9	177.1 (3)
C6—C1—C2—C3	0.2 (6)	C12—C7—C8—C9	−0.7 (5)
C1—C2—C3—C4	1.2 (6)	C7—C8—C9—C10	0.0 (5)
C2—C3—C4—C5	−1.5 (6)	C7—C8—C9—S	177.0 (2)
C3—C4—C5—C6	0.6 (5)	O1—S—C9—C8	154.6 (2)
C3—C4—C5—S	−177.8 (3)	O2—S—C9—C8	24.3 (3)
O1—S—C5—C6	11.1 (3)	C5—S—C9—C8	−89.5 (3)
O2—S—C5—C6	140.7 (3)	O1—S—C9—C10	−28.3 (3)
C9—S—C5—C6	−105.0 (3)	O2—S—C9—C10	−158.6 (3)
O1—S—C5—C4	−170.5 (3)	C5—S—C9—C10	87.6 (3)
O2—S—C5—C4	−40.9 (3)	C8—C9—C10—C11	1.2 (5)
C9—S—C5—C4	73.3 (3)	S—C9—C10—C11	−175.8 (3)
C4—C5—C6—C1	0.8 (5)	C9—C10—C11—C12	−1.5 (6)
S—C5—C6—C1	179.1 (3)	C10—C11—C12—C7	0.8 (6)
N1—C1—C6—C5	176.6 (4)	N2—C7—C12—C11	−177.4 (3)
C2—C1—C6—C5	−1.2 (5)	C8—C7—C12—C11	0.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O1	0.93	2.53	2.913 (4)	105
C8—H8A···O2	0.93	2.53	2.906 (4)	104
N1—H1B···O1i	0.86	2.32	3.147 (5)	161
N2—H2B···O2ii	0.86	2.28	3.079 (4)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯O1	0.93	2.53	2.913 (4)	105
C8—H8A⋯O2	0.93	2.53	2.906 (4)	104
N1—H1B⋯O1i	0.86	2.32	3.147 (5)	161
N2—H2B⋯O2ii	0.86	2.28	3.079 (4)	155

Symmetry codes: (i) ; (ii) .