Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807020983/ci2356sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807020983/ci2356Isup2.hkl |
CCDC reference: 651373
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.022
- wR factor = 0.053
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT431_ALERT_2_B Short Inter HL..A Contact I1 .. O3 .. 3.10 Ang.
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.97 PLAT431_ALERT_2_C Short Inter HL..A Contact I2 .. O6 .. 3.39 Ang.
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For general background, see: Belloni et al. (2005); Kahwa et al. (1986); Parashar et al. (1988); Santos et al. (2001); Tynan et al. (2005).
4-Hydroxy-3-iodo-5-methoxy-benzaldehyde (1 g) was added to an anhydrous ethanol (50 ml), with stirring at 350 K. The resulting yellow solution was filtered and the filtrate was allowed to stand in air at room temperature for 10 d, yielding yellow crystals of (I)
H atoms were placed in calculated positions [O—H = 0.82 Å and C—H = 0.93 (aromatic) or 0.96 Å (methyl)] and refined using a riding model, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(O).
In order to establish control over the preparation of crystalline solid materials so that their architecture and properties are predictable (Belloni et al., 2005; Tynan et al., 2005; Parashar et al., 1988), the synthesis of new and designed crystal structures has become a major strand of modern chemistry. Metal complexes based on Schiff bases have attracted much attention because they can be utilized as model compounds of the active centres
in various proteins and enzymes (Kahwa et al., 1986; Santos et al., 2001). As part of an investigation of the coordination properties of Shiff bases functioning as ligands, we report the synthesis and crystal structure of the title compound, (I).
The asymmetric unit of (I) comprises two independent molecules (Fig. 1), lying on the mirror planes, one at z = 0 and the other at z = 1/2. The two molecules differ in the orientation of the –CHO group by a 180° rotation around its bond with the benzene ring. In both molecules the geometric parameters are normal.
Each independent molecule is linked to a symmetry-equivalent molecule by intermolecular O—H···O hydrogen bonds, forming a chain along the b axis, in the mirror plane. The chains formed by each independent molecule are shown in Fig.2 and Fig.3. Short intermolecular I1···O3(x - 1/2, 1/2 - y, 1 - z) [3.099 (3) Å] and I2···O6(x - 1/2, 1/2 - y, -z) [3.388 (3) Å] contacts are observed between the adjacent chains.]
For general background, see: Belloni et al. (2005); Kahwa et al. (1986); Parashar et al. (1988); Santos et al. (2001); Tynan et al. (2005).
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
C8H7IO3 | F(000) = 1056 |
Mr = 278.04 | Dx = 2.098 Mg m−3 |
Orthorhombic, Pbam | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2 2ab | Cell parameters from 4592 reflections |
a = 16.332 (2) Å | θ = 2.5–26.4° |
b = 16.344 (2) Å | µ = 3.60 mm−1 |
c = 6.5957 (12) Å | T = 293 K |
V = 1760.6 (4) Å3 | Block, yellow |
Z = 8 | 0.20 × 0.16 × 0.12 mm |
Bruker SMART CCD area-detector diffractometer | 1974 independent reflections |
Radiation source: fine-focus sealed tube | 1654 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
φ and ω scans | θmax = 26.4°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −16→20 |
Tmin = 0.533, Tmax = 0.672 | k = −20→19 |
9744 measured reflections | l = −5→8 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.022 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.053 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.025P)2 + 0.749P] where P = (Fo2 + 2Fc2)/3 |
1974 reflections | (Δ/σ)max = 0.001 |
145 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.47 e Å−3 |
C8H7IO3 | V = 1760.6 (4) Å3 |
Mr = 278.04 | Z = 8 |
Orthorhombic, Pbam | Mo Kα radiation |
a = 16.332 (2) Å | µ = 3.60 mm−1 |
b = 16.344 (2) Å | T = 293 K |
c = 6.5957 (12) Å | 0.20 × 0.16 × 0.12 mm |
Bruker SMART CCD area-detector diffractometer | 1974 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1654 reflections with I > 2σ(I) |
Tmin = 0.533, Tmax = 0.672 | Rint = 0.037 |
9744 measured reflections |
R[F2 > 2σ(F2)] = 0.022 | 0 restraints |
wR(F2) = 0.053 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.47 e Å−3 |
1974 reflections | Δρmin = −0.47 e Å−3 |
145 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
I1 | −0.024919 (16) | 0.352244 (16) | 0.5000 | 0.03520 (9) | |
O1 | 0.13388 (17) | 0.45773 (15) | 0.5000 | 0.0385 (7) | |
H1O | 0.1744 | 0.4873 | 0.5000 | 0.058* | |
O2 | 0.29270 (16) | 0.42133 (16) | 0.5000 | 0.0419 (7) | |
O3 | 0.29135 (17) | 0.10050 (16) | 0.5000 | 0.0374 (7) | |
C1 | 0.0976 (2) | 0.3182 (2) | 0.5000 | 0.0271 (8) | |
C2 | 0.1575 (2) | 0.3788 (2) | 0.5000 | 0.0266 (8) | |
C3 | 0.2406 (2) | 0.3558 (2) | 0.5000 | 0.0269 (8) | |
C4 | 0.2620 (2) | 0.2753 (2) | 0.5000 | 0.0292 (8) | |
H4 | 0.3170 | 0.2604 | 0.5000 | 0.035* | |
C5 | 0.2013 (2) | 0.2148 (2) | 0.5000 | 0.0263 (8) | |
C6 | 0.1193 (2) | 0.2362 (2) | 0.5000 | 0.0287 (8) | |
H6 | 0.0791 | 0.1959 | 0.5000 | 0.034* | |
C7 | 0.2227 (3) | 0.1278 (2) | 0.5000 | 0.0321 (9) | |
H7 | 0.1797 | 0.0904 | 0.5000 | 0.038* | |
C8 | 0.3785 (2) | 0.4039 (3) | 0.5000 | 0.0474 (12) | |
H8A | 0.4087 | 0.4542 | 0.5000 | 0.071* | |
H8B | 0.3921 | 0.3728 | 0.3812 | 0.071* | |
I2 | 0.049445 (18) | 0.127572 (19) | 0.0000 | 0.04574 (11) | |
O4 | 0.15122 (18) | −0.03449 (17) | 0.0000 | 0.0434 (7) | |
H4O | 0.1763 | −0.0779 | 0.0000 | 0.065* | |
O5 | 0.30938 (17) | −0.06768 (16) | 0.0000 | 0.0411 (7) | |
O6 | 0.3560 (2) | 0.29765 (18) | 0.0000 | 0.0586 (9) | |
C9 | 0.1756 (2) | 0.1081 (2) | 0.0000 | 0.0311 (9) | |
C10 | 0.2044 (2) | 0.0276 (2) | 0.0000 | 0.0311 (9) | |
C11 | 0.2889 (2) | 0.0137 (2) | 0.0000 | 0.0294 (8) | |
C12 | 0.3422 (2) | 0.0785 (2) | 0.0000 | 0.0329 (9) | |
H12 | 0.3984 | 0.0690 | 0.0000 | 0.039* | |
C13 | 0.3128 (3) | 0.1583 (2) | 0.0000 | 0.0318 (9) | |
C14 | 0.2296 (3) | 0.1732 (2) | 0.0000 | 0.0352 (10) | |
H14 | 0.2101 | 0.2266 | 0.0000 | 0.042* | |
C15 | 0.3720 (3) | 0.2257 (3) | 0.0000 | 0.0402 (10) | |
H15 | 0.4271 | 0.2115 | 0.0000 | 0.048* | |
C16 | 0.3938 (3) | −0.0866 (3) | 0.0000 | 0.0475 (11) | |
H16A | 0.4008 | −0.1449 | 0.0000 | 0.071* | |
H16B | 0.4190 | −0.0638 | 0.1188 | 0.071* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.02010 (14) | 0.03288 (15) | 0.05262 (19) | 0.00134 (10) | 0.000 | 0.000 |
O1 | 0.0261 (15) | 0.0192 (13) | 0.070 (2) | −0.0014 (11) | 0.000 | 0.000 |
O2 | 0.0207 (14) | 0.0257 (14) | 0.079 (2) | −0.0031 (11) | 0.000 | 0.000 |
O3 | 0.0319 (16) | 0.0232 (14) | 0.0570 (19) | 0.0058 (12) | 0.000 | 0.000 |
C1 | 0.0181 (19) | 0.0271 (18) | 0.036 (2) | −0.0006 (15) | 0.000 | 0.000 |
C2 | 0.025 (2) | 0.0206 (17) | 0.034 (2) | 0.0020 (14) | 0.000 | 0.000 |
C3 | 0.022 (2) | 0.0205 (18) | 0.038 (2) | −0.0034 (14) | 0.000 | 0.000 |
C4 | 0.023 (2) | 0.0285 (19) | 0.036 (2) | 0.0047 (15) | 0.000 | 0.000 |
C5 | 0.028 (2) | 0.0206 (17) | 0.030 (2) | 0.0040 (15) | 0.000 | 0.000 |
C6 | 0.028 (2) | 0.0242 (19) | 0.034 (2) | −0.0050 (15) | 0.000 | 0.000 |
C7 | 0.035 (2) | 0.0199 (18) | 0.042 (2) | 0.0007 (16) | 0.000 | 0.000 |
C8 | 0.020 (2) | 0.045 (3) | 0.077 (3) | −0.0009 (19) | 0.000 | 0.000 |
I2 | 0.02894 (17) | 0.05050 (19) | 0.0578 (2) | 0.00543 (12) | 0.000 | 0.000 |
O4 | 0.0333 (16) | 0.0306 (15) | 0.066 (2) | −0.0051 (12) | 0.000 | 0.000 |
O5 | 0.0323 (16) | 0.0268 (14) | 0.064 (2) | 0.0049 (12) | 0.000 | 0.000 |
O6 | 0.067 (2) | 0.0269 (16) | 0.082 (2) | −0.0079 (15) | 0.000 | 0.000 |
C9 | 0.025 (2) | 0.034 (2) | 0.034 (2) | 0.0051 (17) | 0.000 | 0.000 |
C10 | 0.031 (2) | 0.0284 (19) | 0.034 (2) | −0.0059 (16) | 0.000 | 0.000 |
C11 | 0.032 (2) | 0.0216 (19) | 0.035 (2) | 0.0016 (16) | 0.000 | 0.000 |
C12 | 0.028 (2) | 0.036 (2) | 0.035 (2) | −0.0005 (17) | 0.000 | 0.000 |
C13 | 0.040 (2) | 0.0248 (19) | 0.030 (2) | −0.0032 (17) | 0.000 | 0.000 |
C14 | 0.041 (3) | 0.026 (2) | 0.038 (2) | 0.0044 (18) | 0.000 | 0.000 |
C15 | 0.037 (3) | 0.038 (2) | 0.045 (3) | −0.0093 (19) | 0.000 | 0.000 |
C16 | 0.039 (3) | 0.038 (2) | 0.065 (3) | 0.014 (2) | 0.000 | 0.000 |
I1—C1 | 2.077 (4) | I2—C9 | 2.085 (4) |
O1—C2 | 1.347 (4) | O4—C10 | 1.336 (4) |
O1—H1O | 0.8200 | O4—H4O | 0.82 |
O2—C3 | 1.368 (4) | O5—C11 | 1.371 (4) |
O2—C8 | 1.430 (5) | O5—C16 | 1.413 (5) |
O3—C7 | 1.207 (5) | O6—C15 | 1.205 (5) |
C1—C6 | 1.386 (5) | C9—C14 | 1.382 (6) |
C1—C2 | 1.392 (5) | C9—C10 | 1.396 (5) |
C2—C3 | 1.408 (5) | C10—C11 | 1.399 (5) |
C3—C4 | 1.363 (5) | C11—C12 | 1.371 (5) |
C4—C5 | 1.400 (5) | C12—C13 | 1.390 (5) |
C4—H4 | 0.93 | C12—H12 | 0.93 |
C5—C6 | 1.384 (5) | C13—C14 | 1.379 (6) |
C5—C7 | 1.464 (5) | C13—C15 | 1.465 (5) |
C6—H6 | 0.93 | C14—H14 | 0.93 |
C7—H7 | 0.93 | C15—H15 | 0.93 |
C8—H8A | 0.96 | C16—H16A | 0.96 |
C8—H8B | 0.96 | C16—H16B | 0.96 |
C2—O1—H1O | 109.5 | C10—O4—H4O | 109.5 |
C3—O2—C8 | 117.0 (3) | C11—O5—C16 | 116.8 (3) |
C6—C1—C2 | 120.5 (3) | C14—C9—C10 | 120.7 (4) |
C6—C1—I1 | 120.4 (3) | C14—C9—I2 | 120.9 (3) |
C2—C1—I1 | 119.1 (3) | C10—C9—I2 | 118.4 (3) |
O1—C2—C1 | 118.7 (3) | O4—C10—C9 | 119.8 (4) |
O1—C2—C3 | 122.1 (3) | O4—C10—C11 | 121.1 (3) |
C1—C2—C3 | 119.2 (3) | C9—C10—C11 | 119.0 (3) |
C4—C3—O2 | 126.7 (3) | C12—C11—O5 | 126.4 (4) |
C4—C3—C2 | 120.3 (3) | C12—C11—C10 | 120.1 (3) |
O2—C3—C2 | 113.0 (3) | O5—C11—C10 | 113.5 (3) |
C3—C4—C5 | 120.1 (3) | C11—C12—C13 | 120.3 (4) |
C3—C4—H4 | 120.0 | C11—C12—H12 | 119.8 |
C5—C4—H4 | 120.0 | C13—C12—H12 | 119.8 |
C6—C5—C4 | 120.4 (3) | C14—C13—C12 | 120.4 (4) |
C6—C5—C7 | 118.5 (3) | C14—C13—C15 | 121.1 (4) |
C4—C5—C7 | 121.1 (3) | C12—C13—C15 | 118.5 (4) |
C5—C6—C1 | 119.5 (3) | C13—C14—C9 | 119.5 (4) |
C5—C6—H6 | 120.2 | C13—C14—H14 | 120.2 |
C1—C6—H6 | 120.2 | C9—C14—H14 | 120.2 |
O3—C7—C5 | 125.5 (4) | O6—C15—C13 | 126.2 (4) |
O3—C7—H7 | 117.3 | O6—C15—H15 | 116.9 |
C5—C7—H7 | 117.3 | C13—C15—H15 | 116.9 |
O2—C8—H8A | 109.5 | O5—C16—H16A | 109.5 |
O2—C8—H8B | 109.5 | O5—C16—H16B | 109.5 |
H8A—C8—H8B | 109.5 | H16A—C16—H16B | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O2 | 0.82 | 2.21 | 2.661 (4) | 115 |
O1—H1O···O3i | 0.82 | 1.93 | 2.634 (4) | 143 |
O4—H4O···O5 | 0.82 | 2.18 | 2.639 (4) | 116 |
O4—H4O···O6ii | 0.82 | 2.10 | 2.746 (4) | 135 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1; (ii) −x+1/2, y−1/2, −z. |
Experimental details
Crystal data | |
Chemical formula | C8H7IO3 |
Mr | 278.04 |
Crystal system, space group | Orthorhombic, Pbam |
Temperature (K) | 293 |
a, b, c (Å) | 16.332 (2), 16.344 (2), 6.5957 (12) |
V (Å3) | 1760.6 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 3.60 |
Crystal size (mm) | 0.20 × 0.16 × 0.12 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.533, 0.672 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9744, 1974, 1654 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.022, 0.053, 1.03 |
No. of reflections | 1974 |
No. of parameters | 145 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.47, −0.47 |
Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O2 | 0.82 | 2.21 | 2.661 (4) | 115 |
O1—H1O···O3i | 0.82 | 1.93 | 2.634 (4) | 143 |
O4—H4O···O5 | 0.82 | 2.18 | 2.639 (4) | 116 |
O4—H4O···O6ii | 0.82 | 2.10 | 2.746 (4) | 135 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1; (ii) −x+1/2, y−1/2, −z. |
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In order to establish control over the preparation of crystalline solid materials so that their architecture and properties are predictable (Belloni et al., 2005; Tynan et al., 2005; Parashar et al., 1988), the synthesis of new and designed crystal structures has become a major strand of modern chemistry. Metal complexes based on Schiff bases have attracted much attention because they can be utilized as model compounds of the active centres
in various proteins and enzymes (Kahwa et al., 1986; Santos et al., 2001). As part of an investigation of the coordination properties of Shiff bases functioning as ligands, we report the synthesis and crystal structure of the title compound, (I).
The asymmetric unit of (I) comprises two independent molecules (Fig. 1), lying on the mirror planes, one at z = 0 and the other at z = 1/2. The two molecules differ in the orientation of the –CHO group by a 180° rotation around its bond with the benzene ring. In both molecules the geometric parameters are normal.
Each independent molecule is linked to a symmetry-equivalent molecule by intermolecular O—H···O hydrogen bonds, forming a chain along the b axis, in the mirror plane. The chains formed by each independent molecule are shown in Fig.2 and Fig.3. Short intermolecular I1···O3(x - 1/2, 1/2 - y, 1 - z) [3.099 (3) Å] and I2···O6(x - 1/2, 1/2 - y, -z) [3.388 (3) Å] contacts are observed between the adjacent chains.]