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The X-ray analysis of the title compound, C19H19IO5, shows that the orientation of the two benzene rings is cis and confirms the E configuration of the mol­ecule. The occurrence of O—H...O hydrogen-bonding inter­actions results in the formation of centrosymmetric dimers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805030667/dn6255sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805030667/dn6255Isup2.hkl
Contains datablock I

CCDC reference: 287553

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.031
  • wR factor = 0.066
  • Data-to-parameter ratio = 18.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Since the position of an Auger electron emitter (e.g. 77Br, 123I and 125I) vis-à-vis DNA is of paramount importance for its DNA double-strand-break yield and toxicity (Kassis, 2004), the development of a carrier molecule locating the Auger electron emitter in close proximity to the nuclear DNA of cells is of high interest. We have recently focused on the synthesis of Hoechst-skeleton-based ligands, designed by in silico methods (Chen et al., 2004a,b), with predictable iodine-to-DNA distances. The title compound, (I), has been produced as an important intermediate, and its conformation has been determined by X-ray structure analysis and is presented in this report.

As shown in Fig. 1, the orientation of the two benzene rings is cis, thus clearly demonstrating that the conformation of compound (I) is E. The C1—C2—C3—C10 and C2—C3—C10—C11 torsion angles are 174.7 (3) and 169.0 (3)°, respectively, and indicate that the iodine-substited benzene ring and the acrylic acid group are nearly coplanar, whereas the dimethoxy-substituted benzene ring crosses this plane with the dihedral angle 72.50 (7)° between planes C4–C9 and C10–C15. In the crystal structure, strong intermolecular O—H···O hydrogen bonds (Table 1) connect the molecules producing distinct dimers arranged around inversion center (Fig. 2).

Experimental top

To a solution of 4-ethoxy-3-iodobenzaldehyde (2 mmol), prepared according to the method of Harapanhalli et al. (1996), and (3,5-dimethoxyphenyl)acetic acid (2 mmol) in acetic anhydride (10 ml), triethylamine (4 mmol) was added dropwise and the solution was stirred at 363 K for 6 h. Water (6 ml) was then added and the reaction was allowed to continue for 30 min, after which K2CO3 (8 mmol) in water (10 ml) was added dropwise and the reaction warmed to 333 K. The reaction was stirred for an additional 30 min, then cooled to 283 K, and acidified to pH 3 with 6 M HCl. The aqueous solution was extracted with CH2Cl2 (3 × 15 ml), and the organic phases were combined, washed with brine (3 × 15 ml), and dried. The solution was then concentrated under reduced pressure and the residue was recrystallized from ethanol to afford compound (I) (yield: 80%, m.p. 480 K). 1H NMR (d6-DMSO, 200 MHz): δ 7.61 (s, 1H), 7.53 (s, 1H), 7.12 (d, 1H), 6.85 (d, 1H), 6.52 (s, 1H), 6.31 (s, 2H), 4.06 (q, J = 6.6 Hz, 2H), 3.71 (s, 6H), 1.31 (t, J = 6.6 Hz, 3H). HR–MS (ESI), calculated for C19H19IO5: [M+Na]+ 477.0169; found: 477.0188. Crystals suitable for single-crystal X-ray diffraction were obtained by evaporation of an ethanol solution at 298 K.

Refinement top

All H atoms were initially located in a difference Fourier map but they were treated as riding on their parent atoms, with C—H distances of 0.99 (CH2), 0.98 (CH3) and 0.95 Å (aromatic), and an O—H distance of 0.84 Å, with Uiso(H) = 1.5Ueq(methyl C) and 1.2Ueq(C,O).

Computing details top

Data collection: ASTRO (Bruker, 1997); cell refinement: SMART (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. View of the molecule of (I), showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented by circles of arbitrary size.
[Figure 2] Fig. 2. A molecular view of the dimer resulting from the O—H···O hydrogen bonds. H atoms bonded to C atoms have been omitted for clarity. Dotted lines indicate the hydrogen-bonding interactions [symmetry code: (i) 1 − x, −y, 1 − z].
(2E)-2-(3,5-Dimethoxyphenyl)-3-(4-ethoxy-3-iodophenyl)acrylic acid top
Crystal data top
C19H19IO5F(000) = 904
Mr = 454.26Dx = 1.624 Mg m3
Monoclinic, P21/nMelting point: 480 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 12.688 (2) ÅCell parameters from 978 reflections
b = 11.1649 (19) Åθ = 3.1–27.9°
c = 14.229 (2) ŵ = 1.75 mm1
β = 112.861 (2)°T = 193 K
V = 1857.4 (5) Å3Chunk, yellow
Z = 40.20 × 0.16 × 0.12 mm
Data collection top
Bruker CCD
diffractometer
4310 independent reflections
Radiation source: normal-focus sealed tube4085 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
Detector resolution: 836.6 pixels mm-1θmax = 27.9°, θmin = 1.8°
ω scansh = 1616
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 914
Tmin = 0.665, Tmax = 0.811l = 1817
11524 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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066H-atom parameters constrained
S = 1.20 w = 1/[σ2(Fo2) + (0.0209P)2 + 1.9018P]
where P = (Fo2 + 2Fc2)/3
4310 reflections(Δ/σ)max = 0.001
230 parametersΔρmax = 0.94 e Å3
0 restraintsΔρmin = 0.85 e Å3
Crystal data top
C19H19IO5V = 1857.4 (5) Å3
Mr = 454.26Z = 4
Monoclinic, P21/nMo Kα radiation
a = 12.688 (2) ŵ = 1.75 mm1
b = 11.1649 (19) ÅT = 193 K
c = 14.229 (2) Å0.20 × 0.16 × 0.12 mm
β = 112.861 (2)°
Data collection top
Bruker CCD
diffractometer
4310 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4085 reflections with I > 2σ(I)
Tmin = 0.665, Tmax = 0.811Rint = 0.015
11524 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.066H-atom parameters constrained
S = 1.20Δρmax = 0.94 e Å3
4310 reflectionsΔρmin = 0.85 e Å3
230 parameters
Special details top

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
I10.253688 (14)0.575415 (16)0.837858 (14)0.03562 (7)
O10.49958 (15)0.67215 (17)0.94443 (14)0.0343 (4)
O20.43602 (16)0.10649 (19)0.55353 (18)0.0440 (5)
H20.42450.04790.51370.066*
O30.61220 (15)0.08982 (17)0.55559 (15)0.0361 (4)
O40.98142 (15)0.22074 (19)0.83432 (16)0.0432 (5)
O50.83786 (18)0.55924 (18)0.61824 (17)0.0449 (5)
C10.5418 (2)0.1423 (2)0.5816 (2)0.0291 (5)
C20.57425 (19)0.2496 (2)0.64783 (19)0.0269 (5)
C30.4985 (2)0.2936 (2)0.6837 (2)0.0289 (5)
H30.42610.25480.65790.035*
C40.69177 (19)0.2987 (2)0.67223 (18)0.0261 (5)
C50.7855 (2)0.2388 (2)0.7398 (2)0.0299 (5)
H50.77590.16460.76810.036*
C60.8948 (2)0.2876 (2)0.7665 (2)0.0311 (5)
C70.9093 (2)0.3950 (2)0.7253 (2)0.0320 (6)
H70.98350.42870.74430.038*
C80.8138 (2)0.4540 (2)0.6555 (2)0.0318 (5)
C90.7046 (2)0.4069 (2)0.6284 (2)0.0296 (5)
H90.63990.44750.58100.036*
C100.5079 (2)0.3904 (2)0.75544 (19)0.0271 (5)
C110.4065 (2)0.4285 (2)0.76369 (19)0.0273 (5)
H110.33650.38960.72450.033*
C120.4062 (2)0.5213 (2)0.82762 (18)0.0255 (5)
C130.5083 (2)0.5790 (2)0.88722 (18)0.0265 (5)
C140.6101 (2)0.5385 (2)0.88278 (19)0.0283 (5)
H140.68040.57450.92490.034*
C150.6098 (2)0.4465 (2)0.8179 (2)0.0289 (5)
H150.68010.42070.81560.035*
C161.0956 (2)0.2541 (3)0.8506 (2)0.0455 (7)
H16A1.10360.25840.78490.068*
H16B1.14890.19430.89410.068*
H16C1.11280.33250.88410.068*
C170.7481 (3)0.6147 (3)0.5354 (3)0.0539 (8)
H17A0.71900.55860.47800.081*
H17B0.77740.68670.51430.081*
H17C0.68600.63690.55680.081*
C180.6015 (2)0.7377 (2)1.0031 (2)0.0324 (5)
H18A0.64390.75970.96010.039*
H18B0.65210.68891.06120.039*
C190.5628 (3)0.8482 (3)1.0409 (3)0.0554 (9)
H19A0.51060.89400.98270.083*
H19B0.62940.89761.07970.083*
H19C0.52320.82501.08510.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.02552 (9)0.03776 (11)0.04726 (11)0.00453 (7)0.01816 (7)0.00501 (8)
O10.0298 (9)0.0317 (10)0.0417 (10)0.0009 (7)0.0143 (8)0.0135 (8)
O20.0282 (9)0.0435 (12)0.0662 (14)0.0145 (8)0.0248 (9)0.0311 (10)
O30.0278 (9)0.0349 (10)0.0497 (11)0.0055 (7)0.0194 (8)0.0168 (9)
O40.0243 (9)0.0451 (12)0.0520 (12)0.0019 (8)0.0060 (8)0.0048 (10)
O50.0454 (12)0.0363 (11)0.0540 (13)0.0110 (9)0.0205 (10)0.0064 (9)
C10.0240 (11)0.0301 (13)0.0356 (13)0.0036 (10)0.0141 (10)0.0068 (11)
C20.0230 (11)0.0242 (12)0.0345 (12)0.0047 (9)0.0123 (10)0.0076 (10)
C30.0234 (11)0.0284 (13)0.0361 (13)0.0039 (9)0.0128 (10)0.0064 (10)
C40.0240 (11)0.0270 (12)0.0307 (12)0.0039 (9)0.0143 (10)0.0097 (10)
C50.0289 (12)0.0260 (12)0.0376 (13)0.0032 (10)0.0161 (10)0.0035 (10)
C60.0259 (11)0.0329 (14)0.0348 (13)0.0013 (10)0.0121 (10)0.0060 (11)
C70.0254 (11)0.0345 (14)0.0383 (14)0.0089 (10)0.0147 (11)0.0080 (11)
C80.0366 (13)0.0279 (13)0.0366 (14)0.0059 (10)0.0206 (11)0.0045 (10)
C90.0280 (12)0.0290 (13)0.0336 (13)0.0004 (10)0.0139 (10)0.0040 (10)
C100.0252 (11)0.0255 (12)0.0343 (13)0.0023 (9)0.0154 (10)0.0039 (10)
C110.0220 (11)0.0274 (12)0.0339 (12)0.0035 (9)0.0124 (10)0.0018 (10)
C120.0236 (11)0.0241 (12)0.0305 (12)0.0016 (9)0.0126 (9)0.0013 (9)
C130.0287 (11)0.0239 (12)0.0289 (12)0.0005 (9)0.0134 (10)0.0001 (10)
C140.0237 (11)0.0298 (13)0.0318 (12)0.0037 (9)0.0114 (10)0.0046 (10)
C150.0230 (11)0.0312 (13)0.0357 (13)0.0014 (9)0.0151 (10)0.0047 (10)
C160.0249 (12)0.0517 (19)0.0533 (18)0.0018 (12)0.0080 (12)0.0072 (15)
C170.065 (2)0.0438 (18)0.0518 (19)0.0043 (16)0.0211 (17)0.0133 (15)
C180.0340 (13)0.0282 (13)0.0312 (13)0.0030 (10)0.0087 (11)0.0039 (10)
C190.057 (2)0.0393 (18)0.062 (2)0.0012 (15)0.0143 (17)0.0228 (16)
Geometric parameters (Å, º) top
I1—C122.086 (2)C9—H90.9500
O1—C131.352 (3)C10—C151.400 (3)
O1—C181.437 (3)C10—C111.403 (3)
O2—C11.306 (3)C11—C121.380 (3)
O2—H20.8400C11—H110.9500
O3—C11.239 (3)C12—C131.399 (3)
O4—C61.369 (3)C13—C141.392 (3)
O4—C161.425 (3)C14—C151.380 (3)
O5—C81.371 (3)C14—H140.9500
O5—C171.424 (4)C15—H150.9500
C1—C21.480 (3)C16—H16A0.9800
C2—C31.345 (3)C16—H16B0.9800
C2—C41.497 (3)C16—H16C0.9800
C3—C101.459 (3)C17—H17A0.9800
C3—H30.9500C17—H17B0.9800
C4—C51.377 (4)C17—H17C0.9800
C4—C91.398 (4)C18—C191.502 (4)
C5—C61.398 (3)C18—H18A0.9900
C5—H50.9500C18—H18B0.9900
C6—C71.378 (4)C19—H19A0.9800
C7—C81.398 (4)C19—H19B0.9800
C7—H70.9500C19—H19C0.9800
C8—C91.390 (4)
C13—O1—C18118.42 (19)C11—C12—C13120.4 (2)
C1—O2—H2109.5C11—C12—I1120.20 (17)
C6—O4—C16117.4 (2)C13—C12—I1119.35 (17)
C8—O5—C17117.8 (2)O1—C13—C14124.9 (2)
O3—C1—O2122.6 (2)O1—C13—C12116.5 (2)
O3—C1—C2121.3 (2)C14—C13—C12118.6 (2)
O2—C1—C2116.2 (2)C15—C14—C13120.7 (2)
C3—C2—C1118.3 (2)C15—C14—H14119.7
C3—C2—C4124.9 (2)C13—C14—H14119.7
C1—C2—C4116.7 (2)C14—C15—C10121.3 (2)
C2—C3—C10131.3 (2)C14—C15—H15119.3
C2—C3—H3114.4C10—C15—H15119.3
C10—C3—H3114.4O4—C16—H16A109.5
C5—C4—C9120.8 (2)O4—C16—H16B109.5
C5—C4—C2119.8 (2)H16A—C16—H16B109.5
C9—C4—C2119.4 (2)O4—C16—H16C109.5
C4—C5—C6119.8 (2)H16A—C16—H16C109.5
C4—C5—H5120.1H16B—C16—H16C109.5
C6—C5—H5120.1O5—C17—H17A109.5
O4—C6—C7124.8 (2)O5—C17—H17B109.5
O4—C6—C5114.8 (2)H17A—C17—H17B109.5
C7—C6—C5120.4 (2)O5—C17—H17C109.5
C6—C7—C8119.4 (2)H17A—C17—H17C109.5
C6—C7—H7120.3H17B—C17—H17C109.5
C8—C7—H7120.3O1—C18—C19106.3 (2)
O5—C8—C9124.4 (3)O1—C18—H18A110.5
O5—C8—C7114.7 (2)C19—C18—H18A110.5
C9—C8—C7120.9 (2)O1—C18—H18B110.5
C8—C9—C4118.7 (2)C19—C18—H18B110.5
C8—C9—H9120.7H18A—C18—H18B108.7
C4—C9—H9120.7C18—C19—H19A109.5
C15—C10—C11117.5 (2)C18—C19—H19B109.5
C15—C10—C3125.5 (2)H19A—C19—H19B109.5
C11—C10—C3117.0 (2)C18—C19—H19C109.5
C12—C11—C10121.3 (2)H19A—C19—H19C109.5
C12—C11—H11119.3H19B—C19—H19C109.5
C10—C11—H11119.3
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O3i0.841.792.617 (3)169
Symmetry code: (i) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC19H19IO5
Mr454.26
Crystal system, space groupMonoclinic, P21/n
Temperature (K)193
a, b, c (Å)12.688 (2), 11.1649 (19), 14.229 (2)
β (°) 112.861 (2)
V3)1857.4 (5)
Z4
Radiation typeMo Kα
µ (mm1)1.75
Crystal size (mm)0.20 × 0.16 × 0.12
Data collection
DiffractometerBruker CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.665, 0.811
No. of measured, independent and
observed [I > 2σ(I)] reflections
11524, 4310, 4085
Rint0.015
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.066, 1.20
No. of reflections4310
No. of parameters230
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.94, 0.85

Computer programs: ASTRO (Bruker, 1997), SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2003), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O3i0.841.792.617 (3)169
Symmetry code: (i) x+1, y, z+1.
 

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