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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3165.
Published online 2010 November 13. doi:  10.1107/S1600536810045514
PMCID: PMC3011675

4-(4-Pyrid­yl)pyridinium 3-amino-5-carb­oxy-2,4,6-triiodo­benzoate–5-amino-2,4,6-triiodo­isophthalic acid (1/1)

Abstract

In the title ammonium carboxyl­ate–carb­oxy­lic acid co-cystal, C10H9N2 +·C8H3I3NO4 −.C8H4I3NO4, the carboxyl­ate anion and carb­oxy­lic acid mol­ecule are linked by O—H(...)O and N—H(...)O hydrogen bonds to form a chain running along the c axis of the monoclinic unit cell. The chains are linked by pyridinum and pyridine N—H(...)O hydrogen bonds, generating a layer motif. O—H(...)N and O—H(...)O hydrogen bonds are also observed.

Related literature

For the crystal structure of 5-amino-2,4,6-triiodo­isophthalic acid monohydrate, see: Beck & Sheldrick (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o3165-scheme1.jpg

Experimental

Crystal data

  • C10H9N2 +·C8H3I3NO4 ·C8H4I3NO4
  • M r = 1273.83
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3165-efi1.jpg
  • a = 7.7388 (4) Å
  • b = 34.2377 (19) Å
  • c = 13.0739 (7) Å
  • β = 106.506 (1)°
  • V = 3321.3 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 5.66 mm−1
  • T = 295 K
  • 0.08 × 0.06 × 0.04 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.660, T max = 0.805
  • 28196 measured reflections
  • 7506 independent reflections
  • 6365 reflections with I > 2σ(I)
  • R int = 0.037

Refinement

  • R[F 2 > 2σ(F 2)] = 0.032
  • wR(F 2) = 0.082
  • S = 1.03
  • 7506 reflections
  • 429 parameters
  • 8 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 1.25 e Å−3
  • Δρmin = −1.26 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810045514/nk2065sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045514/nk2065Isup2.hkl

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

Acknowledgments

We thank the National Natural Science Foundation of China (grant No. 20773107), Yangzhou University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

5-Amino-2,4,6-triiodoisophthalic acid exists as a monohydrated compound for which the acid and water molecules are linked by extensive O–H···O, O–H···N and N–H···O hydrogen bonds to form a three-dimensional network (Beck & Sheldrick, 2008). The acid furnishes a small number of coordination compounds. The attempt to synthesize a cadmium derivative that can be linked by 4,4'-bipyridine gave instead the co-crystal, C10H9N2+C8H3NO4I3-.C8H4NO4I3 (Scheme I, Fig. 1).

The carboxylate anion and carboxylic acid are linked by O–H···O and N–H···O hydrogen bonds to form a chain running along the c-axis of the monoclinic unit cell. The chains are linked by Npyridinum–H···O and Npyridyl–H···O hydrogen bonds to generate a layer motif (Fig. 2, Table 1).

Experimental

An aqueous solution of cadmium dichloride 2.5 hydrate (0.023 g, 0.1 mmol) in water (5 ml) was added to a mixture of 5-amino-2,4,6-triiodoisophthalic acid (0.056 g, 0.1 mmol) in water (5 ml) and sodium hydroxide (0.2 ml, 0.5 M). To the solution was added 4,4'-bipyridine (0.016 g, 0.1 mmol) in water (5 ml). The solution was filed; slow evaporation yielded deep yellow crystals were collected (30% yield). CH&N elemental analysis. Calc. for C26H16I6N4O8: C 24.51, H 1.27, N 4.43%; Found: C, 24.43; H, 1.29; N, 4.50%.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C).

The amino and acid H-atoms were located in a difference Fourier map, and were refined with distance restraints of N–H 0.88±0.01 and O–H 0.84±0.01 Å; their temperature factors were refined.

The final difference Fourier map had a peak in the vicinity of I5 and a hole in the vicinity of I3.

Figures

Fig. 1.
Displacement ellipsoid plot (Barbour, 2001) of C10H9N2+C8H3NO4I3-.C8H4NO4I3 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Fig. 2.
The hydrogen-bonded layer structure. Each amino group forms only one hydrogen bond; the weaker hydrogen bond is are not shown.

Crystal data

C10H9N2+·C8H3I3NO4·C8H4I3NO4F(000) = 2328
Mr = 1273.83Dx = 2.547 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9939 reflections
a = 7.7388 (4) Åθ = 2.4–27.4°
b = 34.2377 (19) ŵ = 5.66 mm1
c = 13.0739 (7) ÅT = 295 K
β = 106.506 (1)°Prism, yellow
V = 3321.3 (3) Å30.08 × 0.06 × 0.04 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer7506 independent reflections
Radiation source: fine-focus sealed tube6365 reflections with I > 2σ(I)
graphiteRint = 0.037
ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.660, Tmax = 0.805k = −44→44
28196 measured reflectionsl = −16→16

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.0387P)2 + 6.6421P] where P = (Fo2 + 2Fc2)/3
7506 reflections(Δ/σ)max = 0.001
429 parametersΔρmax = 1.25 e Å3
8 restraintsΔρmin = −1.26 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
I10.89589 (4)0.633599 (10)0.26091 (3)0.03827 (9)
I20.17486 (6)0.713602 (10)0.08490 (4)0.05879 (13)
I30.22245 (5)0.537807 (9)0.07851 (3)0.03820 (9)
I40.63572 (4)0.521651 (8)0.65077 (2)0.03066 (8)
I50.57056 (6)0.666532 (10)0.90690 (3)0.04259 (10)
I60.36084 (5)0.672374 (10)0.42509 (3)0.04230 (10)
O10.6872 (5)0.54473 (9)0.2775 (2)0.0315 (7)
O20.6823 (5)0.54041 (10)0.1070 (3)0.0370 (8)
O30.6689 (6)0.71617 (11)0.1148 (3)0.0430 (9)
H3O0.724 (12)0.7376 (14)0.130 (7)0.12 (4)*
O40.6193 (7)0.72189 (11)0.2738 (3)0.0577 (12)
O50.6413 (5)0.58392 (11)0.4353 (3)0.0368 (8)
H5O0.628 (8)0.5720 (16)0.377 (3)0.055 (19)*
O60.3505 (5)0.56703 (11)0.4066 (3)0.0432 (9)
O70.5332 (5)0.56640 (12)0.9082 (3)0.0394 (8)
H7O0.575 (9)0.5570 (19)0.970 (2)0.07 (2)*
O80.8114 (5)0.56830 (13)0.8926 (3)0.0449 (9)
N10.0653 (6)0.62476 (12)0.0256 (4)0.0362 (9)
H110.004 (7)0.6029 (9)0.018 (4)0.045 (16)*
H12−0.001 (7)0.6455 (11)0.029 (5)0.048 (17)*
N20.4185 (7)0.69823 (12)0.6687 (4)0.0423 (11)
H210.461 (8)0.7106 (16)0.730 (3)0.052 (18)*
H220.412 (8)0.7143 (14)0.615 (3)0.048 (17)*
N30.8284 (5)0.47376 (12)0.3134 (3)0.0324 (9)
H30.787 (8)0.4976 (7)0.299 (5)0.055 (18)*
N41.1535 (6)0.28111 (12)0.3578 (4)0.0399 (10)
C10.6421 (6)0.55702 (12)0.1815 (3)0.0255 (9)
C20.5326 (6)0.59425 (12)0.1600 (3)0.0228 (9)
C30.6155 (6)0.63055 (12)0.1880 (3)0.0241 (9)
C40.5151 (6)0.66494 (12)0.1677 (3)0.0258 (9)
C50.3306 (6)0.66243 (12)0.1171 (4)0.0263 (9)
C60.2431 (6)0.62650 (12)0.0846 (3)0.0262 (9)
C70.3500 (6)0.59272 (12)0.1111 (3)0.0248 (9)
C80.6070 (7)0.70421 (13)0.1925 (4)0.0315 (10)
C90.6552 (6)0.57584 (13)0.8604 (3)0.0256 (9)
C100.5792 (6)0.59878 (13)0.7573 (3)0.0230 (9)
C110.5321 (7)0.63773 (13)0.7594 (3)0.0281 (9)
C120.4688 (6)0.66010 (13)0.6662 (4)0.0282 (9)
C130.4532 (6)0.64080 (13)0.5687 (3)0.0256 (9)
C140.5027 (6)0.60201 (12)0.5647 (3)0.0228 (8)
C150.5677 (6)0.58054 (12)0.6596 (3)0.0244 (9)
C160.4885 (6)0.58222 (13)0.4591 (3)0.0267 (9)
C170.8615 (7)0.45571 (14)0.4059 (4)0.0361 (11)
H170.84340.46890.46410.043*
C180.9221 (7)0.41776 (14)0.4184 (4)0.0329 (10)
H180.94610.40560.48460.040*
C190.9471 (6)0.39770 (12)0.3306 (4)0.0258 (9)
C200.9103 (7)0.41793 (14)0.2341 (4)0.0337 (11)
H200.92570.40570.17370.040*
C210.8514 (7)0.45584 (15)0.2286 (4)0.0375 (11)
H21A0.82710.46920.16410.045*
C221.1572 (7)0.30185 (14)0.4440 (4)0.0393 (12)
H22A1.20630.29070.51090.047*
C231.0905 (7)0.33952 (14)0.4377 (4)0.0381 (12)
H231.09550.35320.49990.046*
C241.0163 (6)0.35702 (13)0.3398 (4)0.0273 (9)
C251.0087 (9)0.33460 (16)0.2503 (5)0.0474 (14)
H250.95640.34460.18230.057*
C261.0804 (9)0.29694 (16)0.2632 (5)0.0505 (15)
H261.07660.28230.20260.061*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
I10.03160 (17)0.04546 (19)0.03463 (18)−0.00668 (14)0.00433 (13)0.00376 (14)
I20.0485 (2)0.02261 (17)0.1008 (4)0.00977 (15)0.0140 (2)0.00154 (18)
I30.0456 (2)0.02220 (15)0.03956 (19)−0.00873 (13)0.00046 (15)0.00157 (12)
I40.04117 (18)0.02040 (14)0.02876 (16)0.00191 (12)0.00727 (13)−0.00067 (11)
I50.0665 (2)0.03696 (18)0.02578 (17)0.00401 (16)0.01550 (16)−0.00919 (13)
I60.0586 (2)0.03503 (18)0.02813 (17)0.00338 (15)0.00399 (15)0.00980 (13)
O10.048 (2)0.0260 (16)0.0220 (16)0.0110 (14)0.0115 (14)0.0039 (12)
O20.055 (2)0.0356 (19)0.0235 (16)0.0134 (16)0.0155 (16)0.0004 (14)
O30.063 (3)0.034 (2)0.036 (2)−0.0227 (18)0.0215 (18)−0.0058 (16)
O40.106 (4)0.032 (2)0.041 (2)−0.021 (2)0.031 (2)−0.0154 (17)
O50.048 (2)0.040 (2)0.0256 (18)−0.0024 (16)0.0162 (16)−0.0078 (15)
O60.047 (2)0.044 (2)0.0331 (19)−0.0068 (17)0.0031 (17)−0.0128 (16)
O70.0347 (19)0.054 (2)0.033 (2)0.0066 (16)0.0138 (16)0.0192 (17)
O80.0283 (19)0.066 (3)0.037 (2)0.0010 (17)0.0044 (15)0.0109 (18)
N10.031 (2)0.027 (2)0.044 (2)−0.0006 (17)0.0019 (19)−0.0031 (19)
N20.073 (3)0.020 (2)0.035 (3)0.011 (2)0.017 (2)0.0015 (18)
N30.031 (2)0.027 (2)0.040 (2)0.0103 (17)0.0100 (18)0.0067 (17)
N40.048 (3)0.024 (2)0.052 (3)0.0102 (18)0.020 (2)0.0028 (19)
C10.032 (2)0.0177 (19)0.026 (2)−0.0002 (17)0.0067 (18)0.0001 (17)
C20.035 (2)0.0186 (19)0.0145 (19)0.0001 (17)0.0065 (17)0.0022 (15)
C30.025 (2)0.028 (2)0.020 (2)−0.0031 (17)0.0066 (17)−0.0006 (17)
C40.040 (3)0.0163 (19)0.023 (2)−0.0027 (17)0.0116 (19)−0.0006 (16)
C50.034 (2)0.0162 (19)0.030 (2)0.0028 (17)0.0112 (19)0.0021 (17)
C60.035 (2)0.023 (2)0.022 (2)0.0023 (18)0.0102 (18)0.0008 (17)
C70.035 (2)0.0157 (18)0.023 (2)−0.0047 (17)0.0080 (18)−0.0014 (16)
C80.044 (3)0.018 (2)0.033 (2)−0.0019 (19)0.011 (2)−0.0022 (18)
C90.033 (3)0.025 (2)0.019 (2)−0.0019 (18)0.0067 (18)−0.0033 (16)
C100.024 (2)0.027 (2)0.018 (2)−0.0044 (17)0.0061 (16)−0.0021 (16)
C110.039 (3)0.025 (2)0.021 (2)−0.0028 (19)0.0092 (19)−0.0037 (17)
C120.034 (3)0.020 (2)0.031 (2)−0.0035 (18)0.009 (2)−0.0039 (17)
C130.030 (2)0.027 (2)0.019 (2)0.0010 (18)0.0044 (17)0.0050 (17)
C140.028 (2)0.0212 (19)0.021 (2)−0.0026 (16)0.0088 (17)−0.0015 (16)
C150.028 (2)0.020 (2)0.025 (2)−0.0013 (16)0.0073 (18)−0.0020 (17)
C160.034 (3)0.023 (2)0.021 (2)0.0009 (18)0.0050 (19)0.0002 (17)
C170.041 (3)0.030 (2)0.039 (3)0.011 (2)0.015 (2)−0.001 (2)
C180.043 (3)0.026 (2)0.032 (2)0.010 (2)0.015 (2)0.0045 (19)
C190.027 (2)0.022 (2)0.029 (2)0.0044 (17)0.0088 (18)0.0023 (17)
C200.044 (3)0.027 (2)0.033 (3)0.003 (2)0.015 (2)0.0045 (19)
C210.046 (3)0.035 (3)0.034 (3)0.007 (2)0.015 (2)0.008 (2)
C220.049 (3)0.026 (2)0.042 (3)0.008 (2)0.010 (2)0.004 (2)
C230.050 (3)0.027 (2)0.038 (3)0.007 (2)0.014 (2)0.003 (2)
C240.026 (2)0.025 (2)0.032 (2)0.0052 (17)0.0108 (19)0.0011 (18)
C250.064 (4)0.037 (3)0.039 (3)0.015 (3)0.011 (3)0.004 (2)
C260.078 (4)0.033 (3)0.041 (3)0.016 (3)0.018 (3)−0.004 (2)

Geometric parameters (Å, °)

I1—C32.110 (4)C3—C41.394 (6)
I2—C52.100 (4)C4—C51.395 (7)
I3—C72.110 (4)C4—C81.513 (6)
I4—C152.095 (4)C5—C61.410 (6)
I5—C112.111 (4)C6—C71.407 (6)
I6—C132.108 (4)C9—C101.526 (6)
O1—C11.276 (5)C10—C111.385 (6)
O2—C11.241 (5)C10—C151.402 (6)
O3—C81.307 (6)C11—C121.404 (6)
O3—H3O0.84 (1)C12—C131.409 (6)
O4—C81.203 (6)C13—C141.388 (6)
O5—C161.307 (6)C14—C151.406 (6)
O5—H5O0.84 (1)C14—C161.513 (6)
O6—C161.211 (6)C17—C181.375 (6)
O7—C91.313 (6)C17—H170.9300
O7—H7O0.84 (1)C18—C191.398 (6)
O8—C91.190 (6)C18—H180.9300
N1—C61.374 (6)C19—C201.396 (6)
N1—H110.88 (1)C19—C241.485 (6)
N1—H120.88 (1)C20—C211.371 (7)
N2—C121.366 (6)C20—H200.9300
N2—H210.88 (1)C21—H21A0.9300
N2—H220.88 (1)C22—C231.383 (7)
N3—C171.316 (6)C22—H22A0.9300
N3—C211.323 (7)C23—C241.382 (7)
N3—H30.878 (10)C23—H230.9300
N4—C261.322 (7)C24—C251.387 (7)
N4—C221.325 (7)C25—C261.395 (7)
C1—C21.512 (6)C25—H250.9300
C2—C71.376 (6)C26—H260.9300
C2—C31.399 (6)
C8—O3—H3O111 (6)N2—C12—C11122.2 (4)
C16—O5—H5O108 (4)N2—C12—C13121.2 (4)
C9—O7—H7O115 (5)C11—C12—C13116.6 (4)
C6—N1—H11122 (4)C14—C13—C12122.0 (4)
C6—N1—H12116 (4)C14—C13—I6119.0 (3)
H11—N1—H12113 (6)C12—C13—I6119.0 (3)
C12—N2—H21117 (4)C13—C14—C15120.0 (4)
C12—N2—H22122 (4)C13—C14—C16120.9 (4)
H21—N2—H22110 (6)C15—C14—C16119.1 (4)
C17—N3—C21121.0 (4)C10—C15—C14119.0 (4)
C17—N3—H3127 (4)C10—C15—I4121.8 (3)
C21—N3—H3112 (4)C14—C15—I4119.1 (3)
C26—N4—C22118.5 (4)O6—C16—O5126.6 (4)
O2—C1—O1124.1 (4)O6—C16—C14122.2 (4)
O2—C1—C2119.6 (4)O5—C16—C14111.2 (4)
O1—C1—C2116.3 (4)N3—C17—C18121.6 (5)
C7—C2—C3119.3 (4)N3—C17—H17119.2
C7—C2—C1120.1 (4)C18—C17—H17119.2
C3—C2—C1120.6 (4)C17—C18—C19119.2 (4)
C4—C3—C2120.7 (4)C17—C18—H18120.4
C4—C3—I1119.4 (3)C19—C18—H18120.4
C2—C3—I1119.9 (3)C20—C19—C18117.3 (4)
C3—C4—C5118.6 (4)C20—C19—C24121.0 (4)
C3—C4—C8120.5 (4)C18—C19—C24121.7 (4)
C5—C4—C8120.8 (4)C21—C20—C19119.8 (4)
C4—C5—C6122.4 (4)C21—C20—H20120.1
C4—C5—I2119.7 (3)C19—C20—H20120.1
C6—C5—I2117.9 (3)N3—C21—C20121.1 (5)
N1—C6—C7121.8 (4)N3—C21—H21A119.4
N1—C6—C5121.7 (4)C20—C21—H21A119.4
C7—C6—C5116.4 (4)N4—C22—C23122.1 (5)
C2—C7—C6122.5 (4)N4—C22—H22A119.0
C2—C7—I3119.2 (3)C23—C22—H22A119.0
C6—C7—I3118.3 (3)C24—C23—C22120.6 (5)
O4—C8—O3125.1 (4)C24—C23—H23119.7
O4—C8—C4123.4 (4)C22—C23—H23119.7
O3—C8—C4111.4 (4)C23—C24—C25116.6 (4)
O8—C9—O7125.0 (4)C23—C24—C19121.8 (4)
O8—C9—C10121.5 (4)C25—C24—C19121.5 (4)
O7—C9—C10113.5 (4)C24—C25—C26119.3 (5)
C11—C10—C15119.9 (4)C24—C25—H25120.3
C11—C10—C9121.0 (4)C26—C25—H25120.3
C15—C10—C9119.0 (4)N4—C26—C25122.8 (5)
C10—C11—C12122.5 (4)N4—C26—H26118.6
C10—C11—I5119.9 (3)C25—C26—H26118.6
C12—C11—I5117.5 (3)
O2—C1—C2—C776.5 (6)C10—C11—C12—C130.6 (7)
O1—C1—C2—C7−103.4 (5)I5—C11—C12—C13176.7 (3)
O2—C1—C2—C3−102.6 (5)N2—C12—C13—C14−179.6 (5)
O1—C1—C2—C377.5 (5)C11—C12—C13—C14−1.9 (7)
C7—C2—C3—C40.5 (6)N2—C12—C13—I62.7 (6)
C1—C2—C3—C4179.6 (4)C11—C12—C13—I6−179.6 (3)
C7—C2—C3—I1−179.1 (3)C12—C13—C14—C151.2 (7)
C1—C2—C3—I10.0 (5)I6—C13—C14—C15178.9 (3)
C2—C3—C4—C5−1.2 (6)C12—C13—C14—C16−178.6 (4)
I1—C3—C4—C5178.4 (3)I6—C13—C14—C16−1.0 (6)
C2—C3—C4—C8−176.6 (4)C11—C10—C15—C14−2.0 (6)
I1—C3—C4—C83.0 (5)C9—C10—C15—C14−178.1 (4)
C3—C4—C5—C6−0.8 (7)C11—C10—C15—I4−179.7 (3)
C8—C4—C5—C6174.5 (4)C9—C10—C15—I44.2 (6)
C3—C4—C5—I2−179.9 (3)C13—C14—C15—C100.8 (6)
C8—C4—C5—I2−4.5 (6)C16—C14—C15—C10−179.4 (4)
C4—C5—C6—N1−173.5 (4)C13—C14—C15—I4178.6 (3)
I2—C5—C6—N15.6 (6)C16—C14—C15—I4−1.6 (5)
C4—C5—C6—C73.3 (6)C13—C14—C16—O6−86.0 (6)
I2—C5—C6—C7−177.6 (3)C15—C14—C16—O694.1 (6)
C3—C2—C7—C62.2 (6)C13—C14—C16—O594.3 (5)
C1—C2—C7—C6−176.9 (4)C15—C14—C16—O5−85.6 (5)
C3—C2—C7—I3−175.9 (3)C21—N3—C17—C180.5 (8)
C1—C2—C7—I35.1 (5)N3—C17—C18—C19−0.8 (8)
N1—C6—C7—C2172.8 (4)C17—C18—C19—C200.7 (7)
C5—C6—C7—C2−4.0 (6)C17—C18—C19—C24178.6 (5)
N1—C6—C7—I3−9.1 (6)C18—C19—C20—C21−0.3 (7)
C5—C6—C7—I3174.0 (3)C24—C19—C20—C21−178.2 (5)
C3—C4—C8—O4−96.2 (6)C17—N3—C21—C200.0 (8)
C5—C4—C8—O488.5 (7)C19—C20—C21—N30.0 (8)
C3—C4—C8—O384.2 (5)C26—N4—C22—C23−1.3 (9)
C5—C4—C8—O3−91.1 (5)N4—C22—C23—C240.1 (9)
O8—C9—C10—C11−104.2 (6)C22—C23—C24—C251.6 (8)
O7—C9—C10—C1174.8 (5)C22—C23—C24—C19−178.7 (5)
O8—C9—C10—C1571.9 (6)C20—C19—C24—C23165.6 (5)
O7—C9—C10—C15−109.2 (5)C18—C19—C24—C23−12.2 (7)
C15—C10—C11—C121.3 (7)C20—C19—C24—C25−14.8 (7)
C9—C10—C11—C12177.3 (4)C18—C19—C24—C25167.4 (5)
C15—C10—C11—I5−174.7 (3)C23—C24—C25—C26−2.2 (9)
C9—C10—C11—I51.3 (6)C19—C24—C25—C26178.1 (5)
C10—C11—C12—N2178.4 (5)C22—N4—C26—C250.6 (9)
I5—C11—C12—N2−5.5 (6)C24—C25—C26—N41.2 (10)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H11···O8i0.88 (1)2.22 (4)2.946 (6)141 (5)
N3—H3···O10.88 (1)1.78 (1)2.651 (5)174 (6)
O3—H3o···N4ii0.84 (1)1.75 (2)2.585 (5)171 (9)
O5—H5o···O10.84 (1)1.77 (3)2.568 (4)159 (6)
O7—H7o···O2iii0.84 (1)1.84 (1)2.679 (5)174 (7)

Symmetry codes: (i) x−1, y, z−1; (ii) −x+2, y+1/2, −z+1/2; (iii) x, y, z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NK2065).

References

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  • Beck, T. & Sheldrick, G. M. (2008). Acta Cryst. E64, o1286. [PMC free article] [PubMed]
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

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