1,4-Bis(4,5-dihydro-1H-imidazol-2-yl)benzene-4-amino-benzene-sulfonic acid-water (1/2/2).

The asymmetric unit of the title compound, C(12)H(14)N(4)·2C(6)H(7)NO(3)S·2H(2)O, contains one half of a centrosymmetric 1,4-bis-(4,5-dihydro-1H-imidazol-2-yl)benzene (bib) molecule, one 4-amino-benzene-sulfonic acid molecule and one water mol-ecule. 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, inter-molecular N-H⋯O, O-H⋯N and O-H⋯O inter-actions link the mol-ecules 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 = 596.70

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.140

S = 1.08

2346 reflections

182 parameters

All H-atom parameters refined

Δρmax = 0.45 e Å−3

Δρmin = −0.42 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: SHELXTL and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL and PLATON.

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

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

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

C12H14N4·2C6H7NO3S·2H2O	F(000) = 1256
Mr = 596.70	Dx = 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

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

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(Fo2) + (0.0724P)2 + 1.4974P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2346 reflections	Δρmax = 0.45 e Å−3
182 parameters	Δρmin = −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)

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	0.20619 (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*

	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)

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

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···O3iv	0.86	2.07	2.897 (3)	161
O4—H4A···N3v	0.85	2.08	2.760 (3)	136
O4—H4B···O1vi	0.85	2.20	2.817 (3)	130

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⋯N3iv	0.85	2.08	2.760 (3)	136
O4—H4B⋯O1v	0.85	2.20	2.817 (3)	130

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