Bis(3-amino­phen­yl) sulfone acetonitrile solvate

Yao, W.; Li, F.-S.; Yu, D.-S.; Lu, C.; Zhu, J.-N.

doi:10.1107/S1600536808014840

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1140

doi:10.1107/S1600536808014840

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Bis(3-aminophenyl) sulfone acetonitrile solvate

Wei Yao,^a Fang-Shi Li,^a ^* Da-Sheng Yu,^a Chui Lu ^a and Jin-Na Zhu ^a

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technolgy, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: fangshi.li@njut.edu.cn

(Received 14 May 2008; accepted 16 May 2008; online 21 May 2008)

In the sulfone molecule of the title compound, C₁₂H₁₂N₂O₂S·C₂H₃N, the two benzene rings are oriented at a dihedral angle of 80.69 (3)°. Weak intramolecular C—H⋯O hydrogen bonds result in the formation of two five-membered rings, which both have envelope conformations. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules.

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_r = 289.35
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.055
wR(F²) = 0.135
S = 1.03
2674 reflections
175 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

The title compound, (I), is used for preparing diimide-dicarboxylic acid (Yang et al., 2003) and corresponding truncated dyes analogs of Congo red (Rudyk et al., 2003). As part of our studies in this area, we report herein the synthesis and crystal structure of the title compound, (I).

In the molecule of (I) (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. The asymmetric unit also contains one acetonitrile solvent molecule. Rings A (C1-C6) and B (C7-C12) are, of course, planar and they are oriented at a dihedral angle of A/B = 80.69 (3)°. The weak intramolecular C-H···O hydrogen bonds (Table 1) result in the formation of two five-membered rings C (S/C5/C6/H6A) and D (S/C8/C9/H8A). They adopt envelope conformations, with O1 and O2 atoms displaced by 0.251 (3) and -0.529 (3) Å from the planes of the other ring atoms, respectively.

In the crystal structure, intermolecular N1-H1B···O1ⁱ [H1B···O1 2.32 Å, N1···O1 3.147 (3) Å and N1-H1B···O1 161.0°] and N2-H2B···O2ⁱⁱ [H2B···O2 2.28 Å, N2···O2 3.079 (3) Å and N2-H2B···O2 155.0°] hydrogen bonds [symmetry codes: (i) x + 1/2, y, 1/2 - z; (ii) 1/2 - x, y - 1/2, z] link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

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 top

The title compound, (I), was prepared according to the literature method (Ayyangar et al., 1981). Crystals suitable for X-ray analysis were obtained by dissolving (I) (0.2 g) in acetonitrile (25 ml) and evaporating the solvent slowly at room temperature for about 7 d.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); 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 (Sheldrick, 2008).

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 (I). Hydrogen bonds are shown as dashed lines.

Bis(3-aminophenyl) sulfone acetonitrile solvate top

Crystal data top

C₁₂H₁₂N₂O₂S·C₂H₃N	F(000) = 1216
M_r = 289.35	D_x = 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 = 10–13°
b = 15.559 (3) Å	µ = 0.22 mm⁻¹
c = 20.960 (4) Å	T = 294 K
V = 2990.2 (10) Å³	Block, light yellow
Z = 8	0.40 × 0.30 × 0.30 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1644 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 25.1°, θ_min = 1.9°
ω/2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = 0→18
T_min = 0.917, T_max = 0.937	l = 0→24
2674 measured reflections	3 standard reflections every 120 min
2674 independent reflections	intensity decay: none

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.05P)² + 2P] where P = (F_o² + 2F_c²)/3
2674 reflections	(Δ/σ)_max < 0.001
175 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₂H₁₂N₂O₂S·C₂H₃N	V = 2990.2 (10) Å³
M_r = 289.35	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 9.1690 (18) Å	µ = 0.22 mm⁻¹
b = 15.559 (3) Å	T = 294 K
c = 20.960 (4) Å	0.40 × 0.30 × 0.30 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1644 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.000
T_min = 0.917, T_max = 0.937	3 standard reflections every 120 min
2674 measured reflections	intensity decay: none
2674 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.03	Δρ_max = 0.36 e Å⁻³
2674 reflections	Δρ_min = −0.23 e Å⁻³
175 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1/2, y, −z+1/2; (ii) −x+1/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₂N₂O₂S·C₂H₃N
M_r	289.35
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	294
a, b, c (Å)	9.1690 (18), 15.559 (3), 20.960 (4)
V (Å³)	2990.2 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.40 × 0.30 × 0.30

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.917, 0.937
No. of measured, independent and observed [I > 2σ(I)] reflections	2674, 2674, 1644
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.598

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.135, 1.03
No. of reflections	2674
No. of parameters	175
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.23

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O1	0.93	2.53	2.913 (4)	105.00
C8—H8A···O2	0.93	2.53	2.906 (4)	104.00
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) x+1/2, y, −z+1/2; (ii) −x+1/2, y−1/2, z.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
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Volume 64| Part 6| June 2008| Page o1140

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