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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.
Supporting information
CCDC reference: 242341
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
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.
Crystal data top
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) Å3 | Block, yellow |
Z = 2 | 0.30 × 0.30 × 0.25 mm |
Data collection top
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 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)] = 0.027 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.087 | w = 1/[σ2(Fo2) + (0.1P)2 + 0.4367P] where P = (Fo2 + 2Fc2)/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+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.115 (6) |
Special details top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—O52i | 114.27 (10) | O8—C8—C7 | 128.6 (3) |
O52—S5—C5 | 105.37 (10) | C7—C8—C9 | 117.1 (3) |
O52—S5—O52i | 110.91 (13) | O8—C8—C9 | 114.2 (3) |
O52i—S5—C5 | 105.37 (10) | C8—C9—C10 | 122.0 (3) |
C8—O8—H8 | 106 (3) | N1—C9—C10 | 119.6 (3) |
H1W—O1W—H1Wi | 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—N11i | 120.89 (18) |
C5—C6—C7 | 122.1 (3) | N11—C21—N11i | 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) top
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···O21ii | 0.95 (3) | 1.79 (3) | 2.684 (4) | 155 (4) |
N1—H1···O21iii | 0.95 (3) | 1.79 (3) | 2.684 (4) | 155 (4) |
O1W—H1W···O52iv | 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···O1Wv | 0.98 (7) | 1.79 (7) | 2.565 (5) | 133 (5) |
O8—H8···O1Wvi | 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···O51vii | 0.95 | 2.28 | 3.231 (5) | 178 |
C4—H4···O52 | 0.95 | 2.60 | 3.145 (4) | 117 |
C4—H4···O52i | 0.95 | 2.60 | 3.145 (4) | 117 |
C2—H2···O51viii | 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. |
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