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The crystal structure of guanidinium 8-hydroxy-7-iodo­quino­line-5-sulfonate monohydrate, [(CH6N3+)2(C9H4INO4S2-)·H2O], shows a three-dimensional hydrogen-bonded polymer structure, in which the two guanidinium cations and the water mol­ecule are involved in extensive hydrogen bonding, linking together rows of the dianions. The dianions result from deprotonation of both the sulfonic acid and the phenolic hydroxy groups of the substituted quinoline mol­ecule.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803019275/ww6113sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803019275/ww6113Isup2.hkl
Contains datablock I

CCDC reference: 225706

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.034
  • wR factor = 0.095
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for N1 - C2 = 13.71 su PLAT420_ALERT_2_B D-H Without Acceptor O1W - H1B ... ?
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT128_ALERT_4_C Non-standard setting of Space group P21/c .... P21/a PLAT352_ALERT_3_C Short N-H Bond (0.87A) N11 - H11A = 0.74 Ang. PLAT352_ALERT_3_C Short N-H Bond (0.87A) N12 - H12A = 0.72 Ang. PLAT352_ALERT_3_C Short N-H Bond (0.87A) N13 - H13B = 0.71 Ang.
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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) top
Crystal data top
2CH6N3+·C9H4INO4S·H2OF(000) = 968
Mr = 487.28Dx = 1.829 Mg m3
Monoclinic, P21/aMelting point = 441–445 K
Hall symbol: -P 2yabMo Kα radiation, λ = 0.7107 Å
a = 22.329 (2) ÅCell parameters from 25 reflections
b = 6.9918 (19) Åθ = 12.5–16.1°
c = 11.3456 (8) ŵ = 1.97 mm1
β = 92.646 (7)°T = 295 K
V = 1769.4 (5) Å3Plate, pale brown
Z = 40.50 × 0.50 × 0.20 mm
Data collection top
Rigaku AFC7R
diffractometer
3559 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anodeRint = 0.022
Graphite monochromatorθmax = 27.5°, θmin = 2.5°
ω–2θ scansh = 1028
Absorption correction: ψ scan
TeXsan for Windows (Molecular Structure Corporation, 1999)'
k = 09
Tmin = 0.398, Tmax = 0.674l = 1414
4344 measured reflections3 standard reflections every 150 reflections
4057 independent reflections intensity decay: 18.9%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.095 w = 1/[σ2(Fo2) + (0.0541P)2 + 2.4019P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.018
4057 reflectionsΔρmax = 1.32 e Å3
275 parametersΔρmin = 1.19 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0012 (3)
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
xyzUiso*/Ueq
I70.234933 (10)0.20393 (3)0.419865 (19)0.0396 (1)
S50.41595 (3)0.24664 (12)0.21790 (7)0.0286 (2)
O80.15677 (10)0.1141 (4)0.2775 (2)0.0375 (7)
O510.42226 (11)0.2538 (4)0.0902 (2)0.0371 (7)
O520.43580 (11)0.4257 (4)0.2724 (2)0.0403 (7)
O530.44545 (10)0.0795 (4)0.2715 (2)0.0391 (7)
N10.19050 (12)0.4417 (4)0.1663 (2)0.0351 (8)
C20.20755 (16)0.6037 (6)0.1100 (3)0.0438 (10)
C30.26662 (16)0.6509 (6)0.0988 (3)0.0403 (10)
C40.31098 (15)0.5298 (5)0.1417 (3)0.0357 (9)
C50.33875 (13)0.2197 (4)0.2409 (3)0.0284 (8)
C60.31982 (13)0.0601 (5)0.2996 (3)0.0293 (8)
C70.25883 (13)0.0276 (4)0.3150 (2)0.0280 (8)
C80.21333 (13)0.1474 (5)0.2685 (2)0.0275 (8)
C90.29593 (13)0.3570 (5)0.1969 (2)0.0279 (8)
C100.23374 (14)0.3180 (4)0.2092 (2)0.0275 (8)
N110.07177 (14)0.4162 (5)0.0563 (3)0.0401 (9)
N120.03364 (16)0.2393 (6)0.1001 (3)0.0418 (10)
N130.07837 (16)0.0913 (5)0.0622 (3)0.0425 (10)
C110.06209 (14)0.2483 (5)0.0046 (3)0.0311 (8)
N210.06664 (16)0.3266 (5)0.3711 (3)0.0440 (10)
N220.09874 (18)0.1422 (6)0.5282 (4)0.0551 (11)
N230.00221 (18)0.2601 (7)0.5170 (4)0.0533 (11)
C210.05587 (16)0.2394 (5)0.4719 (3)0.0365 (9)
O1W0.07994 (15)0.7867 (5)0.2855 (3)0.0653 (11)
H20.1774000.6865000.0772000.0520*
H30.2770000.7674000.0617000.0480*
H40.3518000.5626000.1338000.0430*
H60.3486000.02940.3301000.0350*
H11A0.093 (2)0.421 (7)0.108 (4)0.044 (12)*
H11B0.0686 (18)0.513 (6)0.012 (3)0.035 (10)*
H12A0.0259 (19)0.327 (6)0.131 (4)0.031 (11)*
H12B0.026 (2)0.140 (8)0.128 (4)0.053 (14)*
H13A0.0973 (19)0.095 (7)0.130 (4)0.046 (11)*
H13B0.0788 (19)0.003 (7)0.031 (4)0.036 (11)*
H21A0.093 (3)0.281 (8)0.335 (5)0.061 (16)*
H21B0.038 (3)0.370 (8)0.327 (5)0.066 (15)*
H22A0.091 (2)0.076 (7)0.579 (4)0.050 (13)*
H22B0.128 (3)0.133 (8)0.491 (5)0.060 (15)*
H23A0.005 (2)0.207 (7)0.587 (5)0.058 (14)*
H23B0.025 (3)0.321 (9)0.474 (6)0.08 (2)*
H1A0.107 (3)0.891 (9)0.285 (6)0.066 (15)*
H1B0.105 (4)0.681 (9)0.293 (7)0.076 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I70.0391 (2)0.0376 (2)0.0421 (2)0.0032 (1)0.0016 (1)0.0130 (1)
S50.0225 (3)0.0317 (4)0.0314 (4)0.0011 (3)0.0003 (3)0.0016 (3)
O80.0233 (10)0.0446 (13)0.0445 (12)0.0013 (10)0.0021 (9)0.0071 (11)
O510.0362 (12)0.0427 (12)0.0330 (11)0.0010 (10)0.0082 (9)0.0011 (10)
O520.0353 (12)0.0396 (13)0.0457 (13)0.0076 (10)0.0028 (10)0.0075 (11)
O530.0258 (11)0.0402 (13)0.0509 (13)0.0014 (10)0.0036 (9)0.0063 (11)
N10.0291 (13)0.0392 (15)0.0365 (13)0.0049 (11)0.0030 (10)0.0074 (12)
C20.0320 (16)0.053 (2)0.0450 (18)0.0159 (16)0.0121 (14)0.0071 (16)
C30.0432 (19)0.0364 (17)0.0417 (17)0.0015 (14)0.0057 (14)0.0125 (15)
C40.0320 (15)0.0393 (17)0.0363 (15)0.0011 (13)0.0061 (12)0.0066 (13)
C50.0247 (13)0.0335 (15)0.0271 (13)0.0004 (11)0.0009 (11)0.0006 (11)
C60.0282 (14)0.0319 (15)0.0276 (13)0.0023 (12)0.0013 (11)0.0023 (12)
C70.0303 (14)0.0298 (14)0.0238 (12)0.0011 (12)0.0003 (10)0.0024 (11)
C80.0260 (14)0.0343 (15)0.0222 (12)0.0016 (12)0.0017 (10)0.0026 (11)
C90.0281 (14)0.0315 (15)0.0240 (12)0.0032 (12)0.0004 (10)0.0003 (11)
C100.0281 (14)0.0306 (15)0.0234 (12)0.0031 (11)0.0017 (10)0.0002 (11)
N110.0391 (16)0.0363 (16)0.0440 (16)0.0010 (13)0.0082 (13)0.0017 (14)
N120.0471 (18)0.0424 (18)0.0349 (15)0.0042 (15)0.0077 (13)0.0007 (15)
N130.0548 (19)0.0331 (16)0.0392 (16)0.0045 (14)0.0024 (14)0.0025 (14)
C110.0240 (14)0.0369 (16)0.0323 (14)0.0007 (12)0.0018 (11)0.0004 (13)
N210.0361 (16)0.0521 (19)0.0438 (16)0.0065 (14)0.0026 (14)0.0074 (15)
N220.0442 (19)0.067 (2)0.054 (2)0.0010 (18)0.0011 (16)0.0229 (19)
N230.0421 (19)0.068 (2)0.051 (2)0.0082 (18)0.0144 (16)0.0114 (19)
C210.0312 (16)0.0401 (17)0.0381 (16)0.0070 (13)0.0004 (13)0.0050 (14)
O1W0.0522 (18)0.073 (2)0.070 (2)0.0202 (16)0.0062 (15)0.0143 (17)
Geometric parameters (Å, º) top
I7—C72.093 (3)N23—C211.332 (5)
S5—O511.463 (2)N21—H21B0.85 (6)
S5—O521.456 (3)N21—H21A0.80 (6)
S5—O531.460 (3)N22—H22A0.77 (5)
S5—C51.765 (3)N22—H22B0.80 (6)
O8—C81.293 (4)N23—H23B0.87 (7)
O1W—H1B0.93 (7)N23—H23A0.90 (6)
O1W—H1A0.94 (5)C2—C31.371 (5)
N1—C101.369 (4)C3—C41.375 (5)
N1—C21.363 (5)C4—C91.409 (5)
N11—C111.326 (5)C5—C91.429 (4)
N12—C111.322 (5)C5—C61.376 (5)
N13—C111.320 (5)C6—C71.400 (4)
N11—H11B0.84 (4)C7—C81.401 (4)
N11—H11A0.74 (5)C8—C101.453 (4)
N12—H12B0.78 (5)C9—C101.428 (4)
N12—H12A0.72 (4)C2—H20.9506
N13—H13A0.86 (4)C3—H30.9505
N13—H13B0.71 (5)C4—H40.9481
N21—C211.328 (5)C6—H60.9507
N22—C211.315 (5)
O51—S5—O52110.47 (15)S5—C5—C6118.8 (2)
O51—S5—O53112.18 (15)S5—C5—C9121.3 (2)
O51—S5—C5106.82 (15)C5—C6—C7121.0 (3)
O52—S5—O53112.86 (15)C6—C7—C8123.3 (3)
O52—S5—C5108.00 (14)I7—C7—C6118.1 (2)
O53—S5—C5106.13 (14)I7—C7—C8118.5 (2)
H1A—O1W—H1B103 (6)C7—C8—C10115.3 (3)
C2—N1—C10118.9 (3)O8—C8—C7123.8 (3)
C11—N11—H11B116 (3)O8—C8—C10120.8 (3)
H11A—N11—H11B118 (5)C4—C9—C5124.2 (3)
C11—N11—H11A119 (4)C4—C9—C10117.4 (3)
C11—N12—H12B120 (4)C5—C9—C10118.4 (3)
H12A—N12—H12B121 (5)N1—C10—C8116.9 (3)
C11—N12—H12A119 (4)C8—C10—C9121.9 (3)
C11—N13—H13B119 (4)N1—C10—C9121.2 (3)
H13A—N13—H13B117 (5)N1—C2—H2118.77
C11—N13—H13A122 (3)C3—C2—H2118.95
C21—N21—H21B121 (4)C4—C3—H3119.87
C21—N21—H21A115 (4)C2—C3—H3120.17
H21A—N21—H21B113 (6)C3—C4—H4119.84
H22A—N22—H22B125 (5)C9—C4—H4119.97
C21—N22—H22B112 (4)C7—C6—H6119.54
C21—N22—H22A120 (3)C5—C6—H6119.50
C21—N23—H23B117 (4)N11—C11—N12120.1 (3)
C21—N23—H23A120 (3)N11—C11—N13118.8 (3)
H23A—N23—H23B123 (5)N12—C11—N13121.0 (4)
N1—C2—C3122.3 (3)N21—C21—N22119.9 (4)
C2—C3—C4120.0 (4)N21—C21—N23118.9 (4)
C3—C4—C9120.2 (3)N22—C21—N23121.1 (4)
C6—C5—C9119.9 (3)
O51—S5—C5—C6119.5 (3)S5—C5—C6—C7176.9 (2)
O51—S5—C5—C958.6 (3)C6—C5—C9—C103.7 (4)
O52—S5—C5—C6121.6 (3)C5—C6—C7—C82.9 (5)
O52—S5—C5—C960.2 (3)C5—C6—C7—I7173.9 (2)
O53—S5—C5—C60.3 (3)I7—C7—C8—O86.5 (4)
O53—S5—C5—C9178.5 (2)C6—C7—C8—O8176.7 (3)
C10—N1—C2—C32.6 (5)C6—C7—C8—C104.2 (4)
C2—N1—C10—C8180.00 (1)I7—C7—C8—C10172.62 (17)
C2—N1—C10—C90.6 (4)O8—C8—C10—N11.4 (4)
N1—C2—C3—C42.2 (5)O8—C8—C10—C9179.3 (2)
C2—C3—C4—C90.2 (5)C7—C8—C10—C91.6 (4)
C3—C4—C9—C5178.0 (3)C7—C8—C10—N1177.8 (2)
C3—C4—C9—C102.0 (4)C4—C9—C10—N11.6 (4)
C9—C5—C6—C71.3 (5)C5—C9—C10—N1178.4 (3)
S5—C5—C9—C45.6 (4)C5—C9—C10—C82.3 (4)
S5—C5—C9—C10174.4 (2)C4—C9—C10—C8177.7 (3)
C6—C5—C9—C4176.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1A···O8i0.95 (6)1.92 (6)2.865 (4)175 (6)
N11—H11A···N10.74 (5)2.25 (4)2.883 (4)144 (4)
N11—H11B···O51ii0.84 (4)2.06 (4)2.894 (4)169 (4)
N12—H12A···O53ii0.72 (4)2.48 (4)3.121 (5)148 (4)
N12—H12B···O52iii0.78 (5)2.41 (5)3.036 (5)139 (4)
N13—H13A···O80.86 (4)2.09 (4)2.943 (4)170 (4)
N13—H13B···O51iii0.71 (5)2.22 (5)2.925 (4)171 (5)
N21—H21A···O80.80 (6)1.98 (6)2.754 (4)165 (6)
N21—H21B···O53iv0.85 (6)2.16 (7)2.958 (4)156 (6)
N22—H22A···O52v0.77 (5)2.10 (5)2.858 (5)172 (5)
N22—H22B···O80.80 (6)2.54 (6)3.186 (5)139 (6)
N23—H23A···O1Wvi0.90 (6)2.26 (5)2.979 (6)137 (4)
N23—H23B···O53iv0.87 (7)2.46 (7)3.209 (5)144 (6)
C4—H4···O520.94812.57583.180 (4)121.91
C6—H6···O530.95072.41482.841 (4)106.93
Symmetry codes: (i) x, y+1, z; (ii) x+1/2, y+1/2, z; (iii) x+1/2, y1/2, z; (iv) x1/2, y+1/2, z; (v) x+1/2, y1/2, z+1; (vi) x, y+1, z+1.
 

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