1,4-Bis(4,5-dihydro-1H-imidazol-2-yl)benzene–4-amino­benzene­sulfonic acid–water (1/2/2)

Shang, S.-M.; Ren, C.-X.; Wang, X.; Lu, L.-D.; Yang, X.-J.

doi:10.1107/S1600536809032504

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Pages o2221-o2222

doi:10.1107/S1600536809032504

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1,4-Bis(4,5-dihydro-1H-imidazol-2-yl)benzene–4-aminobenzenesulfonic acid–water (1/2/2)

Shao-Ming Shang,^a Chun-Xia Ren,^b Xin Wang,^a ^* Lu-De Lu ^a and Xu-Jie Yang ^a

^aSchool of Chemical and Material Engineering, Nanjing University of Science and Technology, 200 Xiaolingwei Road, Nanjing, Jiangsu Province 210094, People's Republic of China, and ^bSchool of Chemical and Material Engineering, Jiangnan University, 1800 Lihu Road, Wuxi, Jiangsu Province 214122, People's Republic of China
^*Correspondence e-mail: liweijun947@163.com

(Received 6 August 2009; accepted 16 August 2009; online 22 August 2009)

The asymmetric unit of the title compound, C₁₂H₁₄N₄·2C₆H₇NO₃S·2H₂O, contains one half of a centrosymmetric 1,4-bis(4,5-dihydro-1H-imidazol-2-yl)benzene (bib) molecule, one 4-aminobenzenesulfonic acid molecule and one water molecule. In the bib molecule, the imidazole ring adopts an envelope conformation. The benzene rings of bib and 4-aminobenzenesulfonic acid are oriented at a dihedral angle of 21.89 (4)°. In the crystal structure, intermolecular N—H⋯O, O—H⋯N and O—H⋯O interactions link the molecules into a three-dimensional network. Weak π–π contacts between the benzene and imidazole rings and between the benzene rings [centroid–centroid distances = 3.895 (1) and 3.833 (1) Å, respectively] may further stabilize the structure.

Related literature

For general background, see: Jeffrey (1997 ); Thaimattam et al. (1998 ). For related structures, see: Ren et al. (2004a ,b , 2007 , 2009 ). For imidazole bond lengths, see: Haga et al. (1996 ); Hammes et al. (2005 ).

Experimental

Crystal data

C₁₂H₁₄N₄·2C₆H₇NO₃S·2H₂O
M_r = 596.70
Orthorhombic, P b c a
a = 13.6306 (11) Å
b = 12.698 (1) Å
c = 15.5907 (13) Å
V = 2698.5 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 273 K
0.15 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.962, T_max = 0.975
11859 measured reflections
2346 independent reflections
1856 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.140
S = 1.08
2346 reflections
182 parameters
All H-atom parameters refined
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O4	0.82	2.00	2.809 (3)	168
N1—H1A⋯O2ⁱ	0.86	2.22	2.960 (3)	145
N1—H1B⋯O3ⁱⁱ	0.86	2.43	3.200 (3)	150
N1—H1B⋯O1ⁱⁱ	0.86	2.46	3.170 (4)	141
N2—H1⋯O3ⁱⁱⁱ	0.86	2.07	2.897 (3)	161
O4—H4A⋯N3^iv	0.85	2.08	2.760 (3)	136
O4—H4B⋯O1^v	0.85	2.20	2.817 (3)	130
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+2, z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (iv) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (v) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

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: SHELXTL and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809032504/hk2751sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809032504/hk2751Isup2.hkl

checkCIF report

Comment top

Attention has recently focused on the use of supramolecular interactions such as hydrogen bonding and π–π interactions, in addition to coordinate bonds, in the controlled assembly of supramolecular architectures (Jeffrey, 1997). Hydrogen bonds often play a dominant role in crystal engineering because of their combine strength with directionality (Thaimattam et al., 1998). On the other hand, supramolecular systems sustained by soft connections, such as hydrogen bonds, are comparatively more flexible and sensitive to the chemical environment. Consequently hydrogen-bond sustained systems are less designable and remain to be further investigated. We described previously a number of such metal complexes, including imidazole ligand, and have concluded that hydrogen bonding involving this group influences the geometry around the metal atom and the crystallization mechanism (Ren et al., 2004a; Ren et al., 2004b; Ren et al., 2007; Ren et al., 2009). We reported herein the synthesis and crystal structure of the title compound.

The asymmetric unit of the title compound contains one-half of 1,4-bis(4,5-di-hydro-1H-imidazol-2-yl)benzene (bib) ligand, one 4-aminobenzenesulfonic acid (SA) and one water molecules. In bib, the imidazole ring B (N2/N3/C7-C9) adopts envelope conformation with atom C8 displaced by -0.185 (3)Å from the plane of the other ring atoms. Rings A (C1-C6) and C (C10/C11/C12/C10'/C11'/C12') [symmetry code ('): 1 - x, 2 - y, 1 - z] are, of course, planar and they are oriented at a dihedral angle of 21.89 (4)°.

In the crystal structure, intramolecular O-H···O and intermolecular N-H···O, O-H···N and O-H···O interactions (Table 1) link the molecules into a three-dimensional network (Fig. 2), in which they may be effective in the stabilization of the structure. The π–π contacts between the benzene and imidazole rings and between the benzene rings, Cg1—Cg2 and Cg1—Cg3, [where Cg1, Cg2 and Cg3 are centroids of the rings A (C1-C6), B (N2/N3/C7-C9) and C (C10/C11/C12/C10'/C11'/C12'), respectively] may further stabilize the structure, with centroid-centroid distances of 3.895 (1) and 3.833 (1) Å, respectively.

Related literature top

For general background, see: Jeffrey (1997); Thaimattam et al. (1998). For related structures, see: Ren et al. (2004a,b, 2007, 2009). For related literature, see: Haga et al. (1996); Hammes et al. (2005).

Experimental top

For the preparation of 1,4-bis(4,5-dihydro-1H-imidazol-2-yl)benzene, (bib), 1,4-benzenedicarboxylic acid (2.31 g, 13.9 mmol), ethylenediamine (3.70 ml, 50 mmol), ethylenediamine dihydrochloride(6.64 g, 50 mmol) and toluene-p-sulfonic acid (0.208 g, 1.09 mmol) were added to the solvent of ethyleneglycol (20 ml), and the mixture was refluxed for 3 h. About half of the ethylene glycol solvent was then slowly removed by distillation. The residue was dissolved in a mixture of water (40 ml) and concentrated HCl (11 M, 3 ml). The addition of 50% aqueous NaOH gave a yellow precipitate that was purified by recrystallization. The ligand bib was obtained in 83% based on 1,4-benzenedicarboxylic acid (ca 2.50 g). Found: C 66.98; H 6.92; N 26.08%. Calc. for C12H14N4: C 67.27; H 6.59; N 26.15%. Main IR bonds (KBr, cm^-1): 3188m, 2936m, 2866m, 1606 s, 1532 s, 1466 s, 1345m, 1270 s, 1191w, 1080w, 981m, 907w, 767w, 687m. For the preparation of the title compound, to a solution of bib (0.043 g, 0.2 mmol) in MeOH (15 ml), an aqueous solution (5 ml) of SA (0.068 g, 0.4 mmol) was added. The solution was allowed at room temperature in air for 3 d by slow evaporation. Large yellow prismatic crystals were obtained, which were collected by filtration, washed with water and dried in vacuum desiccator over silica gel (0.047 g, 54%). Main IR bonds (KBr,cm^-1): 3424m, 3354m, 3249w, 1655w, 1603m, 1507m, 1119m, 1024 s, 1001m, 698m, 569w.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Hydrogen bond is shown as dashed line [symmetry code ('): 1 - x, 2 - y, 1 - z].
	Fig. 2. A partial packing diagram for the title compound. Hydrogen bonds are shown as dashed lines.

1,4-Bis(4,5-dihydro-1H-imidazol-2-yl)benzene–4-aminobenzenesulfonic acid–water (1/2/2) top

Crystal data top

C₁₂H₁₄N₄·2C₆H₇NO₃S·2H₂O	F(000) = 1256
M_r = 596.70	D_x = 1.469 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3721 reflections
a = 13.6306 (11) Å	θ = 2.6–26.3°
b = 12.698 (1) Å	µ = 0.26 mm⁻¹
c = 15.5907 (13) Å	T = 273 K
V = 2698.5 (4) Å³	Block, yellow
Z = 4	0.15 × 0.12 × 0.10 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2346 independent reflections
Radiation source: fine-focus sealed tube	1856 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −16→15
T_min = 0.962, T_max = 0.975	k = −15→15
11859 measured reflections	l = −18→14

Refinement top

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)] = 0.045	All H-atom parameters refined
wR(F²) = 0.140	w = 1/[σ²(F_o²) + (0.0724P)² + 1.4974P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
2346 reflections	Δρ_max = 0.45 e Å⁻³
182 parameters	Δρ_min = −0.42 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0010 (5)

Crystal data top

C₁₂H₁₄N₄·2C₆H₇NO₃S·2H₂O	V = 2698.5 (4) Å³
M_r = 596.70	Z = 4
Orthorhombic, Pbca	Mo Kα radiation
a = 13.6306 (11) Å	µ = 0.26 mm⁻¹
b = 12.698 (1) Å	T = 273 K
c = 15.5907 (13) Å	0.15 × 0.12 × 0.10 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2346 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	1856 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.975	R_int = 0.036
11859 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.140	All H-atom parameters refined
S = 1.08	Δρ_max = 0.45 e Å⁻³
2346 reflections	Δρ_min = −0.42 e Å⁻³
182 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 > 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	0.20619 (5)	0.82812 (5)	0.31074 (4)	0.0423 (3)
O1	0.29197 (15)	0.8625 (2)	0.26382 (13)	0.0688 (7)
O2	0.1875 (2)	0.71668 (16)	0.30647 (13)	0.0681 (7)
O3	0.12151 (14)	0.88982 (15)	0.28322 (11)	0.0536 (5)
H3A	0.0729	0.8714	0.3104	0.080*
O4	−0.06007 (17)	0.8498 (2)	0.36193 (13)	0.0774 (8)
H4A	−0.0646	0.8028	0.4006	0.093*
H4B	−0.1105	0.8846	0.3470	0.093*
N1	0.2770 (2)	0.9242 (2)	0.67696 (14)	0.0615 (8)
H1A	0.2775	0.8740	0.7140	0.074*
H1B	0.2884	0.9878	0.6930	0.074*
N2	0.51620 (17)	0.7721 (2)	0.34661 (15)	0.0518 (6)
H1	0.5368	0.8180	0.3103	0.062*
N3	0.46812 (18)	0.70826 (19)	0.46926 (16)	0.0530 (6)
C1	0.25816 (19)	0.90302 (19)	0.59303 (15)	0.0384 (6)
C2	0.2594 (2)	0.98296 (19)	0.53090 (16)	0.0398 (6)
H2	0.2705	1.0522	0.5476	0.048*
C3	0.24456 (19)	0.96036 (18)	0.44548 (15)	0.0368 (6)
H3	0.2470	1.0141	0.4050	0.044*
C4	0.22603 (17)	0.85807 (18)	0.41959 (15)	0.0327 (5)
C5	0.22330 (18)	0.77832 (18)	0.48013 (15)	0.0362 (6)
H5	0.2105	0.7095	0.4631	0.043*
C6	0.2394 (2)	0.80063 (19)	0.56551 (15)	0.0392 (6)
H6	0.2378	0.7463	0.6055	0.047*
C7	0.49343 (18)	0.7937 (2)	0.42682 (17)	0.0441 (7)
C8	0.4824 (3)	0.6141 (3)	0.4154 (2)	0.0657 (9)
H8A	0.4241	0.5703	0.4149	0.079*
H8B	0.5377	0.5726	0.4351	0.079*
C9	0.5021 (3)	0.6610 (3)	0.3270 (2)	0.0604 (8)
H9A	0.5604	0.6307	0.3013	0.073*
H9B	0.4468	0.6506	0.2889	0.073*
C10	0.49700 (19)	0.8996 (2)	0.46426 (16)	0.0446 (7)
C11	0.5064 (2)	0.9132 (2)	0.55335 (17)	0.0513 (7)
H11	0.5105	0.8546	0.5890	0.062*
C12	0.4905 (2)	0.9878 (2)	0.41216 (17)	0.0514 (7)
H12	0.4839	0.9796	0.3532	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0514 (5)	0.0491 (4)	0.0264 (4)	−0.0001 (3)	0.0007 (3)	−0.0023 (3)
O1	0.0604 (14)	0.1066 (17)	0.0396 (12)	−0.0006 (13)	0.0178 (10)	0.0025 (11)
O2	0.114 (2)	0.0497 (12)	0.0407 (12)	−0.0013 (12)	−0.0076 (11)	−0.0109 (9)
O3	0.0497 (12)	0.0712 (13)	0.0399 (10)	−0.0024 (10)	−0.0102 (9)	0.0053 (9)
O4	0.0590 (14)	0.128 (2)	0.0449 (13)	0.0017 (14)	−0.0103 (10)	0.0270 (13)
N1	0.097 (2)	0.0549 (15)	0.0321 (12)	−0.0210 (14)	−0.0048 (12)	−0.0035 (10)
N2	0.0504 (14)	0.0678 (16)	0.0371 (13)	−0.0018 (12)	0.0070 (11)	0.0087 (11)
N3	0.0438 (14)	0.0646 (15)	0.0507 (14)	−0.0019 (12)	0.0108 (11)	0.0103 (12)
C1	0.0396 (14)	0.0445 (13)	0.0312 (13)	−0.0052 (12)	0.0007 (11)	−0.0021 (10)
C2	0.0468 (16)	0.0335 (12)	0.0390 (14)	−0.0056 (11)	0.0020 (11)	−0.0019 (10)
C3	0.0389 (14)	0.0360 (12)	0.0356 (13)	0.0004 (11)	0.0006 (11)	0.0053 (10)
C4	0.0317 (13)	0.0359 (12)	0.0304 (12)	0.0021 (10)	0.0005 (10)	0.0013 (9)
C5	0.0457 (15)	0.0315 (12)	0.0314 (13)	−0.0014 (11)	−0.0010 (10)	−0.0005 (9)
C6	0.0466 (15)	0.0374 (12)	0.0335 (13)	−0.0011 (12)	−0.0016 (12)	0.0068 (10)
C7	0.0290 (14)	0.0668 (17)	0.0366 (14)	0.0049 (13)	0.0043 (11)	0.0116 (12)
C8	0.063 (2)	0.071 (2)	0.063 (2)	−0.0182 (17)	0.0129 (16)	0.0054 (16)
C9	0.058 (2)	0.072 (2)	0.0507 (18)	−0.0093 (16)	0.0045 (15)	−0.0012 (15)
C10	0.0330 (14)	0.0646 (17)	0.0361 (14)	0.0076 (13)	0.0063 (11)	0.0110 (12)
C11	0.0509 (17)	0.0654 (18)	0.0377 (15)	0.0104 (14)	0.0065 (12)	0.0146 (13)
C12	0.0494 (17)	0.0729 (19)	0.0318 (14)	0.0101 (15)	0.0042 (12)	0.0094 (13)

Geometric parameters (Å, º) top

S1—O2	1.439 (2)	C3—C4	1.383 (3)
S1—O1	1.447 (2)	C3—H3	0.9300
S1—O3	1.460 (2)	C4—C5	1.385 (3)
S1—C4	1.760 (2)	C5—C6	1.379 (3)
O3—H3A	0.8200	C5—H5	0.9300
O4—H4A	0.8501	C6—H6	0.9300
O4—H4B	0.8501	C7—C10	1.467 (4)
N1—C1	1.360 (3)	C8—C9	1.525 (4)
N1—H1A	0.8600	C8—H8A	0.9700
N1—H1B	0.8600	C8—H8B	0.9700
N2—C7	1.317 (3)	C9—H9A	0.9700
N2—C9	1.455 (4)	C9—H9B	0.9700
N2—H1	0.8600	C10—C12	1.387 (4)
N3—C7	1.317 (3)	C10—C11	1.405 (4)
N3—C8	1.474 (4)	C11—C12ⁱ	1.368 (4)
C1—C6	1.393 (3)	C11—H11	0.9300
C1—C2	1.403 (3)	C12—C11ⁱ	1.368 (4)
C2—C3	1.377 (3)	C12—H12	0.9300
C2—H2	0.9300

O2—S1—O1	114.61 (15)	C4—C5—H5	119.9
O2—S1—O3	111.99 (14)	C5—C6—C1	121.2 (2)
O1—S1—O3	109.17 (13)	C5—C6—H6	119.4
O2—S1—C4	106.51 (12)	C1—C6—H6	119.4
O1—S1—C4	107.34 (13)	N3—C7—N2	111.6 (3)
O3—S1—C4	106.79 (11)	N3—C7—C10	124.3 (2)
S1—O3—H3A	109.5	N2—C7—C10	124.1 (2)
H4A—O4—H4B	120.0	N3—C8—C9	102.8 (3)
C1—N1—H1A	120.0	N3—C8—H8A	111.2
C1—N1—H1B	120.0	C9—C8—H8A	111.2
H1A—N1—H1B	120.0	N3—C8—H8B	111.2
C7—N2—C9	111.7 (2)	C9—C8—H8B	111.2
C7—N2—H1	124.2	H8A—C8—H8B	109.1
C9—N2—H1	124.2	N2—C9—C8	102.3 (2)
C7—N3—C8	110.3 (2)	N2—C9—H9A	111.3
N1—C1—C6	121.0 (2)	C8—C9—H9A	111.3
N1—C1—C2	121.2 (2)	N2—C9—H9B	111.3
C6—C1—C2	117.7 (2)	C8—C9—H9B	111.3
C3—C2—C1	121.0 (2)	H9A—C9—H9B	109.2
C3—C2—H2	119.5	C12—C10—C11	119.0 (3)
C1—C2—H2	119.5	C12—C10—C7	120.4 (2)
C2—C3—C4	120.3 (2)	C11—C10—C7	120.6 (2)
C2—C3—H3	119.8	C12ⁱ—C11—C10	120.3 (3)
C4—C3—H3	119.8	C12ⁱ—C11—H11	119.9
C3—C4—C5	119.5 (2)	C10—C11—H11	119.9
C3—C4—S1	120.81 (18)	C11ⁱ—C12—C10	120.7 (3)
C5—C4—S1	119.67 (18)	C11ⁱ—C12—H12	119.7
C6—C5—C4	120.2 (2)	C10—C12—H12	119.7
C6—C5—H5	119.9

Symmetry code: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O4	0.82	2.00	2.809 (3)	168
N1—H1A···O2ⁱⁱ	0.86	2.22	2.960 (3)	145
N1—H1B···O3ⁱⁱⁱ	0.86	2.43	3.200 (3)	150
N1—H1B···O1ⁱⁱⁱ	0.86	2.46	3.170 (4)	141
N2—H1···O3^iv	0.86	2.07	2.897 (3)	161
O4—H4A···N3^v	0.85	2.08	2.760 (3)	136
O4—H4B···O1^vi	0.85	2.20	2.817 (3)	130

Symmetry codes: (ii) x, −y+3/2, z+1/2; (iii) −x+1/2, −y+2, z+1/2; (iv) x+1/2, y, −z+1/2; (v) x−1/2, −y+3/2, −z+1; (vi) x−1/2, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₄N₄·2C₆H₇NO₃S·2H₂O
M_r	596.70
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	273
a, b, c (Å)	13.6306 (11), 12.698 (1), 15.5907 (13)
V (Å³)	2698.5 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.15 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.962, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	11859, 2346, 1856
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.140, 1.08
No. of reflections	2346
No. of parameters	182
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.42

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O4	0.82	2.00	2.809 (3)	167.8
N1—H1A···O2ⁱ	0.86	2.22	2.960 (3)	144.9
N1—H1B···O3ⁱⁱ	0.86	2.43	3.200 (3)	149.5
N1—H1B···O1ⁱⁱ	0.86	2.46	3.170 (4)	141.0
N2—H1···O3ⁱⁱⁱ	0.86	2.07	2.897 (3)	160.8
O4—H4A···N3^iv	0.85	2.08	2.760 (3)	136.3
O4—H4B···O1^v	0.85	2.20	2.817 (3)	129.6

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1/2, −y+2, z+1/2; (iii) x+1/2, y, −z+1/2; (iv) x−1/2, −y+3/2, −z+1; (v) x−1/2, y, −z+1/2.

Acknowledgements

This work was generously supported by the National Natural Science Foundation of China (grant No. 20701016).

References

Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Haga, M., Ali, M. M. & Arakawa, R. (1996). Angew. Chem. Int. Ed. Engl. 35, 76–78. CrossRef CAS Web of Science Google Scholar
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Volume 65| Part 9| September 2009| Pages o2221-o2222

doi:10.1107/S1600536809032504

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1,4-Bis(4,5-di­hydro-1H-imidazol-2-yl)benzene–4-amino­benzene­sulfonic acid–water (1/2/2)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1,4-Bis(4,5-dihydro-1H-imidazol-2-yl)benzene–4-aminobenzenesulfonic acid–water (1/2/2)