The 1/1/1 adduct hydrate of 8-hydroxy-7-iodo­quinoline-5-sulfonic acid (ferron) with urea

The crystal structure of 8-hydroxy-7-iodo­quinoline-5-sulfonic acid-urea-water, C₉H₆INO₄S·CH₄N₂O·H₂O, shows the zwitterionic (quinoline-sulfonate group) ferron mol­ecule lying in a crystallographic mirror plane which related two of the sulfonate O atoms. Both the urea and the water mol­ecule lie across the same plane and are inter-associated with the ferron mol­ecules both within and between the planes by extensive hydrogen bonding, involving most available donor and acceptor sites on all three mol­ecules. This includes a cyclic R₂²(8) sulfonate-urea association. The result is a three-dimensional layered structure.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.027
• wR factor = 0.087
• Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.55
PLAT432_ALERT_2_C Short Inter X...Y Contact  O8     ..  C21     ..       3.00 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON for Windows (Spek, 1999); software used to prepare material for publication: PLATON for Windows.

(I)

Crystal data

C9H6INO4S·CH4N2O·H2O	F(000) = 420
Mr = 429.19	Dx = 2.071 Mg m^−3
Monoclinic, P21/m	Melting point = 502.1–503.3 K
Hall symbol: -P 2yb	Mo Kα radiation, λ = 0.71069 Å
a = 10.025 (3) Å	Cell parameters from 25 reflections
b = 7.335 (3) Å	θ = 12.5–16.9°
c = 9.845 (3) Å	µ = 2.51 mm^−1
β = 108.05 (2)°	T = 298 K
V = 688.3 (4) Å^3	Block, yellow
Z = 2	0.30 × 0.30 × 0.25 mm

Data collection

Rigaku rotating anode diffractometer	1637 reflections with I > 2σ(I)
Radiation source: Rigaku AFC-7R	Rint = 0.029
Graphite monochromator	θmax = 27.5°, θmin = 2.5°
ω–2θ scans	h = −5→13
Absorption correction: ψ scan (TEXSAN for Windows; Molecular Structure Corporation, 1999)	k = 0→9
Tmin = 0.485, Tmax = 0.534	l = −12→12
1898 measured reflections	3 standard reflections every 150 reflections
1698 independent reflections	intensity decay: 1.4%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.087	w = 1/[σ^2(Fo^2) + (0.1P)^2 + 0.4367P] where P = (Fo^2 + 2Fc^2)/3
S = 0.89	(Δ/σ)max = 0.012
1698 reflections	Δρmax = 1.16 e Å^−3
140 parameters	Δρmin = −1.34 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.115 (6)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 (Ų)

	x	y	z	Uiso*/Ueq
I7	1.18718 (2)	0.250000	0.40545 (2)	0.0305 (1)
S5	0.59432 (8)	0.250000	0.15406 (8)	0.0195 (2)
O8	1.0727 (3)	0.250000	0.6945 (3)	0.0383 (9)
O51	0.6558 (3)	0.250000	0.0395 (3)	0.0300 (7)
O52	0.5141 (2)	0.4139 (3)	0.16091 (19)	0.0299 (5)
N1	0.8145 (3)	0.250000	0.7066 (3)	0.0236 (8)
C2	0.6901 (4)	0.250000	0.7238 (4)	0.0323 (10)
C3	0.5689 (4)	0.250000	0.6052 (4)	0.0397 (13)
C4	0.5820 (4)	0.250000	0.4701 (4)	0.0319 (10)
C5	0.7383 (3)	0.250000	0.3150 (3)	0.0191 (8)
C6	0.8731 (4)	0.250000	0.3091 (3)	0.0217 (8)
C7	0.9898 (3)	0.250000	0.4326 (3)	0.0200 (8)
C8	0.9737 (3)	0.250000	0.5674 (3)	0.0208 (8)
C9	0.8336 (4)	0.250000	0.5746 (3)	0.0202 (8)
C10	0.7151 (3)	0.250000	0.4501 (3)	0.0205 (8)
O21	−0.0156 (3)	0.250000	−0.0224 (3)	0.0254 (7)
N11	0.1878 (2)	0.4068 (3)	0.0289 (2)	0.0308 (6)
C21	0.1157 (4)	0.250000	0.0098 (3)	0.0229 (8)
O1W	0.3417 (3)	0.250000	0.7870 (4)	0.0366 (9)
H1	0.895 (4)	0.250000	0.789 (3)	0.038 (3)*
H2	0.682000	0.250000	0.817700	0.0390*
H3	0.478300	0.250000	0.617800	0.0480*
H4	0.500200	0.250000	0.389800	0.0390*
H6	0.887500	0.250000	0.218200	0.0260*
H8	1.163 (7)	0.250000	0.675 (6)	0.044 (10)*
H11A	0.277 (3)	0.410 (3)	0.044 (3)	0.039 (4)*
H11B	0.133 (4)	0.517 (5)	0.007 (3)	0.036 (9)*
H1W	0.405 (4)	0.330 (6)	0.824 (4)	0.049 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I7	0.0180 (2)	0.0458 (2)	0.0292 (2)	0.0000	0.0095 (1)	0.0000
S5	0.0173 (4)	0.0257 (4)	0.0127 (4)	0.0000	0.0006 (3)	0.0000
O8	0.0175 (12)	0.077 (2)	0.0164 (11)	0.0000	−0.0008 (10)	0.0000
O51	0.0299 (13)	0.0468 (14)	0.0123 (10)	0.0000	0.0049 (9)	0.0000
O52	0.0241 (8)	0.0323 (8)	0.0282 (8)	0.0086 (7)	0.0005 (7)	0.0012 (7)
N1	0.0199 (14)	0.0393 (14)	0.0108 (11)	0.0000	0.0038 (10)	0.0000
C2	0.0266 (19)	0.055 (2)	0.0158 (15)	0.0000	0.0075 (14)	0.0000
C3	0.0175 (16)	0.081 (3)	0.0224 (17)	0.0000	0.0088 (14)	0.0000
C4	0.0164 (17)	0.061 (2)	0.0185 (15)	0.0000	0.0056 (13)	0.0000
C5	0.0172 (15)	0.0252 (13)	0.0135 (13)	0.0000	0.0028 (11)	0.0000
C6	0.0175 (15)	0.0313 (14)	0.0160 (12)	0.0000	0.0046 (11)	0.0000
C7	0.0122 (14)	0.0310 (15)	0.0175 (13)	0.0000	0.0057 (11)	0.0000
C8	0.0180 (15)	0.0288 (14)	0.0144 (13)	0.0000	0.0034 (11)	0.0000
C9	0.0181 (14)	0.0285 (14)	0.0121 (13)	0.0000	0.0017 (11)	0.0000
C10	0.0161 (14)	0.0280 (14)	0.0162 (13)	0.0000	0.0034 (11)	0.0000
O21	0.0178 (13)	0.0334 (12)	0.0208 (11)	0.0000	0.0000 (9)	0.0000
N11	0.0206 (10)	0.0299 (10)	0.0419 (12)	−0.0040 (8)	0.0095 (9)	−0.0036 (9)
C21	0.0219 (16)	0.0288 (14)	0.0160 (13)	0.0000	0.0029 (11)	0.0000
O1W	0.0205 (14)	0.0383 (14)	0.0456 (17)	0.0000	0.0023 (12)	0.0000

Geometric parameters (Å, º)

I7—C7	2.077 (3)	C2—C3	1.400 (6)
S5—O51	1.443 (3)	C3—C4	1.376 (5)
S5—O52	1.460 (2)	C4—C10	1.408 (5)
S5—C5	1.782 (3)	C5—C10	1.419 (4)
O8—C8	1.335 (4)	C5—C6	1.370 (5)
O8—H8	0.98 (7)	C6—C7	1.402 (4)
O21—C21	1.255 (5)	C7—C8	1.386 (4)
O1W—H1W	0.86 (4)	C8—C9	1.428 (5)
N1—C2	1.310 (5)	C9—C10	1.418 (4)
N1—C9	1.371 (4)	C2—H2	0.95
N1—H1	0.95 (3)	C3—H3	0.95
N11—C21	1.340 (3)	C4—H4	0.95
N11—H11A	0.86 (3)	C6—H6	0.95
N11—H11B	0.96 (4)
O51—S5—O52	114.27 (10)	I7—C7—C8	121.4 (2)
O51—S5—C5	105.69 (16)	I7—C7—C6	117.4 (2)
O51—S5—O52^i	114.27 (10)	O8—C8—C7	128.6 (3)
O52—S5—C5	105.37 (10)	C7—C8—C9	117.1 (3)
O52—S5—O52^i	110.91 (13)	O8—C8—C9	114.2 (3)
O52^i—S5—C5	105.37 (10)	C8—C9—C10	122.0 (3)
C8—O8—H8	106 (3)	N1—C9—C10	119.6 (3)
H1W—O1W—H1W^i	86 (4)	N1—C9—C8	118.4 (3)
C2—N1—C9	122.7 (3)	C4—C10—C9	117.1 (3)
C9—N1—H1	119 (2)	C5—C10—C9	118.2 (3)
C2—N1—H1	119 (2)	C4—C10—C5	124.7 (3)
C21—N11—H11B	116 (2)	C3—C2—H2	120
C21—N11—H11A	122.3 (15)	N1—C2—H2	120
H11A—N11—H11B	120 (3)	C2—C3—H3	120
N1—C2—C3	120.5 (3)	C4—C3—H3	120
C2—C3—C4	119.2 (4)	C3—C4—H4	119
C3—C4—C10	120.9 (3)	C10—C4—H4	120
C6—C5—C10	119.3 (3)	C5—C6—H6	119
S5—C5—C10	120.7 (2)	C7—C6—H6	119
S5—C5—C6	120.0 (2)	O21—C21—N11^i	120.89 (18)
C5—C6—C7	122.1 (3)	N11—C21—N11^i	118.2 (3)
C6—C7—C8	121.1 (3)	O21—C21—N11	120.89 (18)
O51—S5—C5—C6	0.00 (2)	S5—C5—C10—C4	0.00 (2)
O51—S5—C5—C10	180.00 (2)	C5—C6—C7—I7	180.00 (2)
O52—S5—C5—C6	−121.32 (10)	C5—C6—C7—C8	0.00 (2)
O52—S5—C5—C10	58.68 (10)	C6—C7—C8—C9	0.00 (2)
C2—N1—C9—C8	180.00 (2)	C6—C7—C8—O8	180.00 (2)
C9—N1—C2—C3	0.00 (2)	I7—C7—C8—O8	0.00 (2)
C2—N1—C9—C10	0.00 (2)	I7—C7—C8—C9	180.00 (2)
N1—C2—C3—C4	0.00 (2)	C7—C8—C9—N1	180.00 (2)
C2—C3—C4—C10	0.00 (2)	O8—C8—C9—C10	180.00 (2)
C3—C4—C10—C9	0.00 (2)	C7—C8—C9—C10	0.00 (2)
C3—C4—C10—C5	180.00 (2)	O8—C8—C9—N1	0.00 (2)
S5—C5—C6—C7	180.00 (2)	N1—C9—C10—C4	0.00 (2)
C10—C5—C6—C7	0.00 (2)	N1—C9—C10—C5	180.00 (2)
C6—C5—C10—C9	0.00 (2)	C8—C9—C10—C4	180.00 (2)
S5—C5—C10—C9	180.00 (2)	C8—C9—C10—C5	0.00 (2)
C6—C5—C10—C4	180.00 (2)

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O8	0.95 (3)	2.25 (3)	2.628 (5)	103 (2)
N1—H1···O21^ii	0.95 (3)	1.79 (3)	2.684 (4)	155 (4)
N1—H1···O21^iii	0.95 (3)	1.79 (3)	2.684 (4)	155 (4)
O1W—H1W···O52^iv	0.86 (4)	2.03 (4)	2.823 (3)	153 (4)
O8—H8···I7	0.98 (7)	2.74 (6)	3.382 (3)	124 (4)
O8—H8···O1W^v	0.98 (7)	1.79 (7)	2.565 (5)	133 (5)
O8—H8···O1W^vi	0.98 (7)	1.79 (7)	2.565 (5)	133 (5)
N11—H11A···O52	0.86 (3)	2.30 (3)	3.124 (3)	161 (3)
C2—H2···O51^vii	0.95	2.28	3.231 (5)	178
C4—H4···O52	0.95	2.60	3.145 (4)	117
C4—H4···O52^i	0.95	2.60	3.145 (4)	117
C2—H2···O51^viii	0.95	2.28	3.231 (5)	178
C3—H3···O1W	0.95	2.46	3.304 (5)	147
C6—H6···O51	0.95	2.44	2.865 (4)	107

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