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In the title compound, C7H5I2NO3, catemeric hydrogen bonding is present involving the carboxyl group of one mol­ecule and the ketone group of a translationally related neighbour.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680100722X/ob6039sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680100722X/ob6039Isup2.hkl
Contains datablock I

CCDC reference: 170292

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.050
  • wR factor = 0.136
  • Data-to-parameter ratio = 19.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
DIFMN_02 Alert C The minimum difference density is < -0.1*ZMAX*0.75 _refine_diff_density_min given = -4.105 Test value = -3.975 DIFMN_03 Alert C The minimum difference density is < -0.1*ZMAX*0.75 The relevant atom site should be identified. RINTA_01 Alert C The value of Rint is greater than 0.10 Rint given 0.105
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
3 Alert Level C = Please check

Computing details top

Data collection: DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997).

3,5-Diiodo-4-oxo-1,4-dihydropyridine-1-acetic acid top
Crystal data top
C7H5I2NO3F(000) = 736
Mr = 404.92Dx = 2.658 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.5577 (2) ÅCell parameters from 2295 reflections
b = 10.7752 (3) Åθ = 2.7–27.5°
c = 11.0632 (3) ŵ = 6.19 mm1
β = 97.3860 (9)°T = 150 K
V = 1011.68 (5) Å3Lozenge, colourless
Z = 40.40 × 0.10 × 0.05 mm
Data collection top
Enraf-Nonius KappaCCD area-detector
diffractometer
2295 independent reflections
Radiation source: Enraf-Nonius FR591 rotating-anode2145 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.106
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 2.7°
φ and ω scans to fill Ewald sphereh = 1111
Absorption correction: multi-scan
using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995)
k = 1313
Tmin = 0.191, Tmax = 0.747l = 1314
8844 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0986P)2 + 0.3356P]
where P = (Fo2 + 2Fc2)/3
2295 reflections(Δ/σ)max = 0.001
120 parametersΔρmax = 1.29 e Å3
0 restraintsΔρmin = 4.11 e Å3
Special details top

Experimental. Please note cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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
I11.17472 (4)0.09424 (3)0.09697 (3)0.02768 (18)
I21.08528 (3)0.47217 (3)0.29897 (3)0.02279 (18)
O11.2523 (4)0.2722 (3)0.1428 (3)0.0238 (7)
O20.5283 (4)0.2825 (3)0.0559 (3)0.0257 (7)
H2'0.44460.28190.08800.026 (7)*
O30.3844 (4)0.3885 (4)0.0926 (4)0.0307 (8)
N10.8087 (4)0.3449 (3)0.0295 (3)0.0198 (8)
C10.6585 (5)0.3827 (5)0.0976 (4)0.0219 (9)
H1A0.65050.34450.17950.026 (7)*
H1B0.66100.47380.10890.026 (7)*
C20.8607 (6)0.4027 (4)0.0776 (4)0.0199 (9)
H20.79490.46130.11070.026 (7)*
C31.0062 (5)0.3771 (4)0.1376 (4)0.0187 (8)
C41.1152 (5)0.2911 (4)0.0912 (4)0.0192 (9)
C51.0465 (5)0.2307 (4)0.0192 (4)0.0197 (9)
C60.9003 (5)0.2603 (5)0.0767 (4)0.0213 (9)
H60.86240.22060.15140.026 (7)*
C70.5088 (6)0.3506 (4)0.0426 (5)0.0217 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0233 (3)0.0360 (3)0.0238 (3)0.00914 (11)0.00323 (17)0.00365 (12)
I20.0179 (3)0.0314 (3)0.0186 (2)0.00322 (10)0.00060 (16)0.00359 (11)
O10.0127 (14)0.0398 (18)0.0187 (15)0.0021 (13)0.0007 (12)0.0007 (14)
O20.0133 (15)0.040 (2)0.0236 (16)0.0010 (13)0.0027 (13)0.0024 (15)
O30.0154 (16)0.0390 (19)0.036 (2)0.0047 (14)0.0028 (15)0.0045 (16)
N10.0122 (17)0.0269 (19)0.0196 (19)0.0010 (14)0.0012 (15)0.0006 (15)
C10.012 (2)0.036 (2)0.017 (2)0.0027 (17)0.0012 (17)0.0018 (18)
C20.015 (2)0.029 (2)0.017 (2)0.0001 (16)0.0047 (17)0.0005 (17)
C30.016 (2)0.024 (2)0.016 (2)0.0021 (17)0.0011 (16)0.0005 (17)
C40.014 (2)0.029 (2)0.0144 (19)0.0027 (17)0.0006 (17)0.0038 (17)
C50.016 (2)0.028 (2)0.0161 (19)0.0015 (16)0.0054 (17)0.0016 (17)
C60.0115 (19)0.030 (2)0.022 (2)0.0036 (17)0.0012 (17)0.0014 (19)
C70.019 (2)0.026 (2)0.020 (2)0.0016 (18)0.0016 (17)0.0008 (17)
Geometric parameters (Å, º) top
I1—C52.085 (4)C1—C71.526 (7)
I2—C32.094 (4)C1—H1A0.9900
O1—C41.253 (5)C1—H1B0.9900
O2—C71.305 (6)C2—C31.362 (7)
O2—H2'0.8400C2—H20.9500
O3—C71.206 (6)C3—C41.455 (7)
N1—C61.350 (6)C4—C51.441 (6)
N1—C21.361 (6)C5—C61.366 (6)
N1—C11.462 (5)C6—H60.9500
C7—O2—H2'109.5C2—C3—I2119.5 (4)
C6—N1—C2120.3 (4)C4—C3—I2117.5 (3)
C6—N1—C1120.3 (4)O1—C4—C5124.7 (4)
C2—N1—C1119.2 (4)O1—C4—C3123.2 (4)
N1—C1—C7117.3 (4)C5—C4—C3112.1 (4)
N1—C1—H1A108.0C6—C5—C4122.6 (4)
C7—C1—H1A108.0C6—C5—I1118.1 (3)
N1—C1—H1B108.0C4—C5—I1119.3 (3)
C7—C1—H1B108.0N1—C6—C5121.3 (4)
H1A—C1—H1B107.2N1—C6—H6119.3
N1—C2—C3120.5 (4)C5—C6—H6119.3
N1—C2—H2119.7O3—C7—O2125.7 (5)
C3—C2—H2119.7O3—C7—C1118.4 (4)
C2—C3—C4123.0 (4)O2—C7—C1115.9 (4)
C6—N1—C1—C7115.3 (5)O1—C4—C5—C6175.5 (5)
C2—N1—C1—C769.5 (6)C3—C4—C5—C65.0 (6)
C6—N1—C2—C30.9 (7)O1—C4—C5—I13.6 (6)
C1—N1—C2—C3174.3 (4)C3—C4—C5—I1176.0 (3)
N1—C2—C3—C41.7 (7)C2—N1—C6—C50.2 (7)
N1—C2—C3—I2177.9 (3)C1—N1—C6—C5174.9 (4)
C2—C3—C4—O1176.1 (4)C4—C5—C6—N13.0 (7)
I2—C3—C4—O10.2 (6)I1—C5—C6—N1177.9 (3)
C2—C3—C4—C54.4 (6)N1—C1—C7—O3174.8 (4)
I2—C3—C4—C5179.3 (3)N1—C1—C7—O25.7 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.841.832.665 (5)174
C1—H1A···O1ii0.992.583.503 (6)156
C2—H2···O3iii0.952.223.095 (6)152
C6—H6···O1ii0.952.353.217 (6)151
Symmetry codes: (i) x1, y, z; (ii) x1/2, y+1/2, z1/2; (iii) x+1, y+1, z.
 

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