5-Amino-2,4,6-triiodo­isophthalic acid–4,4′-bipyridine N,N′-dioxide–water (1/1/1)

Zhang, K.-L.; Zhang, J.-B.; Ng, S.W.

doi:10.1107/S1600536811007276

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o793

doi:10.1107/S1600536811007276

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5-Amino-2,4,6-triiodoisophthalic acid–4,4′-bipyridine N,N′-dioxide–water (1/1/1)

Kou-Lin Zhang,^a Jin-Bo Zhang ^a and Seik Weng Ng ^b ^*

^aCollege of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 25 February 2011; accepted 25 February 2011; online 5 March 2011)

The aromatic rings of the N,N′-dioxide molecule in the title compound, C₈H₄NI₃O₄·C₁₀H₈N₂O₂·H₂O, are twisted by 14.0 (2)°. The –CO₂H substituents of the 5-amino-2,4,6-triiodoisophthalic acid are twisted by 83.0 (2) and 86.5 (2)° out of the plane of the aromatic ring. In the crystal, the three components are linked by O—H⋯O hydrogen bonds into a three-dimensional network. An N—H⋯O interaction also occurs. One of the amino H atom is not involved in hydrogen bonding.

Related literature

For the structure of the monohydrated carboxylic acid, see: Beck & Sheldrick (2008 ). For the 4,4′-bipyridinium 5-amino-2,4,6-triiodoisophthalate co-crystal of carboxylic acid, see: Zhang et al. (2010 ).

Experimental

Crystal data

C₈H₄NI₃O₄·C₁₀H₈N₂O₂·H₂O
M_r = 765.02
Monoclinic, P 2₁ /n
a = 7.5000 (2) Å
b = 17.0808 (4) Å
c = 16.523 (3) Å
β = 94.349 (2)°
V = 2110.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 4.49 mm⁻¹
T = 100 K
0.20 × 0.05 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.467, T_max = 0.807
10861 measured reflections
4660 independent reflections
4112 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.068
S = 1.04
4660 reflections
304 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.97 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O5ⁱ	0.84 (3)	1.64 (3)	2.478 (4)	174 (6)
O3—H3⋯O6ⁱⁱ	0.84 (3)	1.63 (3)	2.465 (4)	170 (7)
O1W—H1w1⋯O2	0.84 (3)	2.30 (3)	3.073 (4)	154 (4)
O1W—H1w2⋯O5ⁱⁱⁱ	0.84 (3)	2.12 (3)	2.945 (4)	167 (5)
N1—H11⋯O1w^iv	0.88 (3)	2.20 (3)	2.906 (5)	138 (4)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x+1, -y+1, -z+1; (iii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811007276/bt5482sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811007276/bt5482Isup2.hkl

checkCIF report

Comment top

The attempt at synthesizing the 4,4'-bipyridine adduct of cadmium 5-amino-2,4,6-triiodoisophthalate gave instead a co-crystal having a monoprotonated 4,4'-bipyridinium 5-amino-2,4,6-triiodoisophthalate as one component and a carboxylic acid as the other (Zhang et al., 2010). Replacing the metal ion by a zinc ion, and with 4,4'-bipyridine N,N'-dioxide in place of 4,4'-bipyridine, gave instead the title monohydrated neutral co-crystal, C₁₀H₈N₂O₂^.C₈H₄NI₂O₄^.H₂O (Scheme I, Fig. 1). In the N-heterocycle, the rings are twisted by 14.0 (2) °. In the carboxylic acid, the –CO₂H substituents are nearly perpendicular to the aromatic ring. The three components are linked by O–H···O hydrogen bonds into a layer structure (Table 1).

Related literature top

For the structure of the monohydrated carboxylic acid, see: Beck & Sheldrick (2008). For the 4,4'-bipyridinium 5-amino-2,4,6-triiodoisophthalate co-crystal of carboxylic acid, see: Zhang et al. (2010).

Experimental top

Zinc nitrate hexahydrate (58 mg, 0.2 mmol), 5-amino-2,4,6-triiodoisophthalic acid (59 mg, 0.1 mmol), 4,4'-bipyridine N,N'-dioxide (56 mg, 0.1 mmol), sodium hydroxide (4 mg, 0.1 mmol) and water (6 ml) were heated ain a 16-ml, Teflon-lined Parr bomb. The bomb was heated at 343 K for 3 days. Greenish-yellow crystals were isolated from the cool mixture.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C₁₀H₈N₂O₂^.C₈H₄NI₃O₄^.H₂O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

5-Amino-2,4,6-triiodoisophthalic acid–4,4'-bipyridine N,N'-dioxide–water (1/1/1) top

Crystal data top

C₈H₄NI₃O₄·C₁₀H₈N₂O₂·H₂O	F(000) = 1432
M_r = 765.02	D_x = 2.408 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5995 reflections
a = 7.5000 (2) Å	θ = 2.4–29.2°
b = 17.0808 (4) Å	µ = 4.49 mm⁻¹
c = 16.523 (3) Å	T = 100 K
β = 94.349 (2)°	Prism, yellow
V = 2110.6 (4) Å³	0.20 × 0.05 × 0.05 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4660 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4112 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.032
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.4°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −16→21
T_min = 0.467, T_max = 0.807	l = −21→21
10861 measured reflections

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.068	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0304P)²] where P = (F_o² + 2F_c²)/3
4660 reflections	(Δ/σ)_max = 0.001
304 parameters	Δρ_max = 0.73 e Å⁻³
6 restraints	Δρ_min = −0.97 e Å⁻³

Crystal data top

C₈H₄NI₃O₄·C₁₀H₈N₂O₂·H₂O	V = 2110.6 (4) Å³
M_r = 765.02	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.5000 (2) Å	µ = 4.49 mm⁻¹
b = 17.0808 (4) Å	T = 100 K
c = 16.523 (3) Å	0.20 × 0.05 × 0.05 mm
β = 94.349 (2)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4660 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	4112 reflections with I > 2σ(I)
T_min = 0.467, T_max = 0.807	R_int = 0.032
10861 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	6 restraints
wR(F²) = 0.068	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.73 e Å⁻³
4660 reflections	Δρ_min = −0.97 e Å⁻³
304 parameters

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

	x	y	z	U_iso*/U_eq
I1	0.32943 (3)	0.507910 (15)	0.632563 (14)	0.01280 (8)
I2	0.05617 (3)	0.779896 (16)	0.826265 (14)	0.01348 (8)
I3	0.05801 (3)	0.802046 (16)	0.463723 (14)	0.01291 (8)
O1	0.0967 (4)	0.57411 (17)	0.81306 (15)	0.0145 (6)
O2	0.3866 (4)	0.60594 (16)	0.82653 (15)	0.0139 (6)
O3	0.1102 (4)	0.59971 (17)	0.45040 (15)	0.0140 (6)
O4	0.3967 (4)	0.63963 (17)	0.46318 (15)	0.0158 (6)
O5	0.3523 (4)	0.98110 (17)	0.57244 (15)	0.0171 (6)
O6	0.8488 (4)	0.46621 (17)	0.67957 (15)	0.0165 (6)
O1W	0.6478 (5)	0.49085 (19)	0.91589 (18)	0.0215 (7)
N1	0.0344 (5)	0.8521 (2)	0.64989 (18)	0.0164 (8)
N2	0.4406 (4)	0.9148 (2)	0.59092 (18)	0.0134 (7)
N3	0.8019 (4)	0.5409 (2)	0.66729 (18)	0.0126 (7)
C1	0.2386 (5)	0.6091 (2)	0.7914 (2)	0.0111 (8)
C2	0.2034 (5)	0.6574 (2)	0.7142 (2)	0.0112 (8)
C3	0.1342 (5)	0.7325 (2)	0.7169 (2)	0.0099 (8)
C4	0.0991 (5)	0.7782 (2)	0.6459 (2)	0.0109 (8)
C5	0.1361 (5)	0.7429 (2)	0.5724 (2)	0.0105 (8)
C6	0.2090 (5)	0.6682 (2)	0.5683 (2)	0.0105 (8)
C7	0.2412 (5)	0.6246 (2)	0.6397 (2)	0.0098 (8)
C8	0.2487 (5)	0.6338 (2)	0.4873 (2)	0.0119 (8)
C9	0.4693 (5)	0.8909 (3)	0.6689 (2)	0.0145 (9)
H9	0.4314	0.9225	0.7116	0.017*
C10	0.5527 (6)	0.8211 (2)	0.6861 (2)	0.0149 (9)
H10	0.5746	0.8057	0.7412	0.018*
C11	0.6067 (5)	0.7718 (2)	0.6253 (2)	0.0117 (8)
C12	0.5799 (5)	0.8009 (2)	0.5456 (2)	0.0129 (8)
H12A	0.6200	0.7712	0.5019	0.016*
C13	0.4974 (5)	0.8712 (2)	0.5301 (2)	0.0144 (8)
H13	0.4798	0.8894	0.4757	0.017*
C14	0.7350 (5)	0.5812 (2)	0.7277 (2)	0.0123 (8)
H14	0.7275	0.5570	0.7791	0.015*
C15	0.6778 (5)	0.6564 (2)	0.7165 (2)	0.0130 (8)
H15	0.6333	0.6841	0.7606	0.016*
C16	0.6833 (5)	0.6936 (2)	0.6412 (2)	0.0133 (8)
C17	0.7574 (5)	0.6498 (2)	0.5799 (2)	0.0127 (8)
H17	0.7661	0.6726	0.5279	0.015*
C18	0.8169 (5)	0.5751 (2)	0.5935 (2)	0.0130 (8)
H18	0.8688	0.5469	0.5516	0.016*
H1	0.121 (7)	0.543 (2)	0.852 (2)	0.038 (16)*
H3	0.130 (8)	0.582 (3)	0.4044 (17)	0.06 (2)*
H1W1	0.563 (5)	0.523 (2)	0.907 (3)	0.031 (15)*
H1W2	0.694 (6)	0.505 (3)	0.9614 (14)	0.026 (14)*
H11	−0.016 (6)	0.877 (2)	0.6082 (18)	0.023 (13)*
H12	−0.008 (6)	0.870 (3)	0.6942 (16)	0.029 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.01590 (14)	0.00943 (15)	0.01275 (13)	0.00111 (10)	−0.00109 (10)	−0.00108 (10)
I2	0.01938 (15)	0.01238 (15)	0.00890 (12)	0.00079 (11)	0.00256 (10)	−0.00099 (10)
I3	0.01642 (14)	0.01286 (15)	0.00930 (12)	0.00009 (11)	−0.00009 (10)	0.00293 (10)
O1	0.0152 (15)	0.0146 (16)	0.0137 (13)	−0.0024 (12)	0.0007 (11)	0.0074 (12)
O2	0.0138 (15)	0.0163 (16)	0.0112 (12)	0.0002 (12)	−0.0024 (11)	0.0021 (12)
O3	0.0166 (15)	0.0146 (16)	0.0105 (13)	−0.0011 (12)	−0.0015 (11)	−0.0046 (12)
O4	0.0153 (15)	0.0192 (17)	0.0135 (13)	0.0012 (13)	0.0053 (11)	0.0015 (12)
O5	0.0252 (17)	0.0114 (16)	0.0140 (13)	0.0066 (13)	−0.0029 (12)	−0.0030 (12)
O6	0.0256 (17)	0.0105 (15)	0.0131 (13)	0.0048 (13)	0.0001 (12)	−0.0012 (12)
O1W	0.0281 (19)	0.0166 (18)	0.0185 (15)	0.0011 (15)	−0.0061 (14)	−0.0044 (13)
N1	0.025 (2)	0.014 (2)	0.0102 (16)	0.0045 (16)	0.0026 (15)	0.0014 (15)
N2	0.0162 (18)	0.0109 (19)	0.0130 (15)	−0.0011 (14)	0.0001 (13)	−0.0032 (14)
N3	0.0123 (17)	0.0139 (19)	0.0117 (15)	0.0012 (14)	0.0007 (13)	−0.0001 (14)
C1	0.020 (2)	0.009 (2)	0.0052 (16)	−0.0004 (17)	0.0029 (15)	−0.0027 (15)
C2	0.0104 (19)	0.012 (2)	0.0104 (17)	−0.0018 (16)	−0.0024 (14)	−0.0001 (15)
C3	0.0112 (19)	0.011 (2)	0.0080 (16)	−0.0031 (16)	0.0021 (14)	−0.0052 (15)
C4	0.0080 (19)	0.011 (2)	0.0134 (18)	−0.0018 (16)	−0.0006 (14)	−0.0013 (15)
C5	0.013 (2)	0.013 (2)	0.0055 (16)	−0.0021 (16)	−0.0017 (14)	0.0029 (15)
C6	0.0103 (19)	0.011 (2)	0.0102 (17)	−0.0017 (16)	0.0004 (14)	0.0003 (15)
C7	0.0083 (19)	0.008 (2)	0.0134 (17)	0.0020 (15)	0.0000 (14)	0.0006 (15)
C8	0.018 (2)	0.008 (2)	0.0098 (17)	0.0039 (17)	−0.0009 (15)	0.0059 (15)
C9	0.016 (2)	0.016 (2)	0.0114 (17)	0.0011 (17)	−0.0027 (15)	−0.0044 (16)
C10	0.021 (2)	0.015 (2)	0.0082 (17)	−0.0017 (18)	0.0001 (15)	−0.0001 (16)
C11	0.0058 (18)	0.015 (2)	0.0142 (18)	−0.0047 (16)	0.0001 (14)	−0.0012 (16)
C12	0.013 (2)	0.013 (2)	0.0125 (18)	−0.0043 (17)	0.0006 (15)	−0.0046 (16)
C13	0.016 (2)	0.015 (2)	0.0121 (17)	−0.0024 (18)	0.0012 (15)	−0.0024 (16)
C14	0.0111 (19)	0.017 (2)	0.0082 (17)	−0.0022 (17)	0.0008 (14)	−0.0036 (16)
C15	0.013 (2)	0.013 (2)	0.0124 (17)	−0.0029 (17)	0.0011 (15)	−0.0031 (16)
C16	0.010 (2)	0.017 (2)	0.0131 (18)	−0.0032 (17)	−0.0002 (15)	−0.0033 (16)
C17	0.0102 (19)	0.017 (2)	0.0106 (17)	−0.0027 (17)	0.0017 (14)	−0.0011 (16)
C18	0.0089 (19)	0.019 (2)	0.0117 (17)	0.0011 (17)	0.0028 (14)	−0.0029 (16)

Geometric parameters (Å, º) top

I1—C7	2.106 (4)	C3—C4	1.417 (5)
I2—C3	2.103 (4)	C4—C5	1.402 (5)
I3—C5	2.104 (4)	C5—C6	1.392 (6)
O1—C1	1.294 (5)	C6—C7	1.400 (5)
O1—H1	0.84 (3)	C6—C8	1.512 (5)
O2—C1	1.214 (4)	C9—C10	1.365 (6)
O3—C8	1.302 (5)	C9—H9	0.9500
O3—H3	0.84 (3)	C10—C11	1.394 (6)
O4—C8	1.212 (5)	C10—H10	0.9500
O5—N2	1.335 (4)	C11—C12	1.407 (5)
O6—N3	1.335 (4)	C11—C16	1.469 (6)
O1W—H1W1	0.84 (3)	C12—C13	1.366 (6)
O1W—H1W2	0.84 (3)	C12—H12A	0.9500
N1—C4	1.356 (5)	C13—H13	0.9500
N1—H11	0.88 (3)	C14—C15	1.362 (6)
N1—H12	0.88 (3)	C14—H14	0.9500
N2—C13	1.347 (5)	C15—C16	1.402 (5)
N2—C9	1.354 (5)	C15—H15	0.9500
N3—C14	1.341 (5)	C16—C17	1.408 (5)
N3—C18	1.364 (5)	C17—C18	1.365 (6)
C1—C2	1.525 (5)	C17—H17	0.9500
C2—C3	1.386 (5)	C18—H18	0.9500
C2—C7	1.401 (5)

C1—O1—H1	111 (4)	O4—C8—O3	126.9 (3)
C8—O3—H3	113 (4)	O4—C8—C6	120.4 (4)
H1W1—O1W—H1W2	103 (5)	O3—C8—C6	112.6 (3)
C4—N1—H11	124 (3)	N2—C9—C10	120.0 (4)
C4—N1—H12	122 (3)	N2—C9—H9	120.0
H11—N1—H12	108 (4)	C10—C9—H9	120.0
O5—N2—C13	118.6 (3)	C9—C10—C11	122.0 (4)
O5—N2—C9	121.0 (3)	C9—C10—H10	119.0
C13—N2—C9	120.4 (4)	C11—C10—H10	119.0
O6—N3—C14	119.2 (3)	C10—C11—C12	115.6 (4)
O6—N3—C18	120.4 (3)	C10—C11—C16	123.4 (3)
C14—N3—C18	120.4 (4)	C12—C11—C16	121.0 (3)
O2—C1—O1	126.0 (3)	C13—C12—C11	121.2 (4)
O2—C1—C2	121.2 (3)	C13—C12—H12A	119.4
O1—C1—C2	112.8 (3)	C11—C12—H12A	119.4
C3—C2—C7	120.0 (3)	N2—C13—C12	120.7 (4)
C3—C2—C1	121.0 (3)	N2—C13—H13	119.7
C7—C2—C1	119.0 (4)	C12—C13—H13	119.7
C2—C3—C4	121.9 (3)	N3—C14—C15	121.0 (4)
C2—C3—I2	120.9 (3)	N3—C14—H14	119.5
C4—C3—I2	117.0 (3)	C15—C14—H14	119.5
N1—C4—C5	122.5 (3)	C14—C15—C16	121.2 (4)
N1—C4—C3	121.1 (3)	C14—C15—H15	119.4
C5—C4—C3	116.4 (4)	C16—C15—H15	119.4
C6—C5—C4	122.7 (3)	C15—C16—C17	116.0 (4)
C6—C5—I3	119.0 (2)	C15—C16—C11	122.2 (4)
C4—C5—I3	118.2 (3)	C17—C16—C11	121.7 (3)
C5—C6—C7	119.4 (3)	C18—C17—C16	121.4 (4)
C5—C6—C8	120.2 (3)	C18—C17—H17	119.3
C7—C6—C8	120.4 (3)	C16—C17—H17	119.3
C6—C7—C2	119.6 (4)	N3—C18—C17	119.9 (3)
C6—C7—I1	119.4 (3)	N3—C18—H18	120.0
C2—C7—I1	120.9 (3)	C17—C18—H18	120.0

O2—C1—C2—C3	−97.1 (5)	C5—C6—C8—O4	94.5 (5)
O1—C1—C2—C3	82.9 (5)	C7—C6—C8—O4	−87.0 (5)
O2—C1—C2—C7	83.2 (5)	C5—C6—C8—O3	−85.4 (5)
O1—C1—C2—C7	−96.8 (4)	C7—C6—C8—O3	93.1 (4)
C7—C2—C3—C4	0.2 (6)	O5—N2—C9—C10	177.0 (4)
C1—C2—C3—C4	−179.5 (4)	C13—N2—C9—C10	−1.5 (6)
C7—C2—C3—I2	174.9 (3)	N2—C9—C10—C11	−1.6 (6)
C1—C2—C3—I2	−4.8 (5)	C9—C10—C11—C12	3.9 (6)
C2—C3—C4—N1	−178.8 (4)	C9—C10—C11—C16	−174.8 (4)
I2—C3—C4—N1	6.3 (5)	C10—C11—C12—C13	−3.4 (6)
C2—C3—C4—C5	0.8 (6)	C16—C11—C12—C13	175.4 (4)
I2—C3—C4—C5	−174.1 (3)	O5—N2—C13—C12	−176.5 (3)
N1—C4—C5—C6	177.4 (4)	C9—N2—C13—C12	2.0 (6)
C3—C4—C5—C6	−2.1 (6)	C11—C12—C13—N2	0.6 (6)
N1—C4—C5—I3	−7.7 (5)	O6—N3—C14—C15	−176.9 (3)
C3—C4—C5—I3	172.7 (3)	C18—N3—C14—C15	1.2 (6)
C4—C5—C6—C7	2.5 (6)	N3—C14—C15—C16	1.3 (6)
I3—C5—C6—C7	−172.3 (3)	C14—C15—C16—C17	−2.4 (6)
C4—C5—C6—C8	−179.0 (4)	C14—C15—C16—C11	174.0 (4)
I3—C5—C6—C8	6.2 (5)	C10—C11—C16—C15	12.1 (6)
C5—C6—C7—C2	−1.4 (6)	C12—C11—C16—C15	−166.5 (4)
C8—C6—C7—C2	−179.9 (4)	C10—C11—C16—C17	−171.6 (4)
C5—C6—C7—I1	174.5 (3)	C12—C11—C16—C17	9.7 (6)
C8—C6—C7—I1	−4.0 (5)	C15—C16—C17—C18	1.1 (6)
C3—C2—C7—C6	0.1 (6)	C11—C16—C17—C18	−175.4 (4)
C1—C2—C7—C6	179.8 (3)	O6—N3—C18—C17	175.6 (3)
C3—C2—C7—I1	−175.7 (3)	C14—N3—C18—C17	−2.5 (6)
C1—C2—C7—I1	4.0 (5)	C16—C17—C18—N3	1.3 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5ⁱ	0.84 (3)	1.64 (3)	2.478 (4)	174 (6)
O3—H3···O6ⁱⁱ	0.84 (3)	1.63 (3)	2.465 (4)	170 (7)
O1W—H1w1···O2	0.84 (3)	2.30 (3)	3.073 (4)	154 (4)
O1W—H1w2···O5ⁱⁱⁱ	0.84 (3)	2.12 (3)	2.945 (4)	167 (5)
N1—H11···O1w^iv	0.88 (3)	2.20 (3)	2.906 (5)	138 (4)

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

Experimental details

Crystal data
Chemical formula	C₈H₄NI₃O₄·C₁₀H₈N₂O₂·H₂O
M_r	765.02
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	7.5000 (2), 17.0808 (4), 16.523 (3)
β (°)	94.349 (2)
V (Å³)	2110.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.49
Crystal size (mm)	0.20 × 0.05 × 0.05

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.467, 0.807
No. of measured, independent and observed [I > 2σ(I)] reflections	10861, 4660, 4112
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.068, 1.04
No. of reflections	4660
No. of parameters	304
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.97

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5ⁱ	0.84 (3)	1.64 (3)	2.478 (4)	174 (6)
O3—H3···O6ⁱⁱ	0.84 (3)	1.63 (3)	2.465 (4)	170 (7)
O1W—H1w1···O2	0.84 (3)	2.30 (3)	3.073 (4)	154 (4)
O1W—H1w2···O5ⁱⁱⁱ	0.84 (3)	2.12 (3)	2.945 (4)	167 (5)
N1—H11···O1w^iv	0.88 (3)	2.20 (3)	2.906 (5)	138 (4)

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

Acknowledgements

We thank the Key Laboratory of Environmental Material and Environmental Engineering of Jiangsu Province, Yangzhou University and the University of Malaya for supporting this study.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Beck, T. & Sheldrick, G. M. (2008). Acta Cryst. E64, o1286. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, K.-L., Diao, G.-W. & Ng, S. W. (2010). Acta Cryst. E66, o3165. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 4| April 2011| Page o793

doi:10.1107/S1600536811007276

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

5-Amino-2,4,6-tri­iodo­isophthalic acid–4,4′-bi­pyridine N,N′-dioxide–water (1/1/1)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

5-Amino-2,4,6-triiodoisophthalic acid–4,4′-bipyridine N,N′-dioxide–water (1/1/1)