5-Amino-2,4,6-triiodo-isophthalic acid-4,4'-bipyridine N,N'-dioxide-water (1/1/1).

The aromatic rings of the N,N'-dioxide molecule in the title compound, C(8)H(4)NI(3)O(4)·C(10)H(8)N(2)O(2)·H(2)O, are twisted by 14.0 (2)°. The -CO(2)H substituents of the 5-amino-2,4,6-triiodo-isophthalic 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 inter-action 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 = 765.02

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.068

S = 1.04

4660 reflections

304 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.73 e Å−3

Δρmin = −0.97 e Å−3

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 ▶).

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

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

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

C8H4NI3O4·C10H8N2O2·H2O	F(000) = 1432
Mr = 765.02	Dx = 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

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	Rint = 0.032
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.4°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −16→21
Tmin = 0.467, Tmax = 0.807	l = −21→21
10861 measured reflections

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(Fo2) + (0.0304P)2] where P = (Fo2 + 2Fc2)/3
4660 reflections	(Δ/σ)max = 0.001
304 parameters	Δρmax = 0.73 e Å−3
6 restraints	Δρmin = −0.97 e Å−3

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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···O1wiv	0.88 (3)	2.20 (3)	2.906 (5)	138 (4)

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⋯O1wiv	0.88 (3)	2.20 (3)	2.906 (5)	138 (4)

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