Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047216/at2410sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047216/at2410Isup2.hkl |
CCDC reference: 667259
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.004 Å
- R factor = 0.050
- wR factor = 0.135
- Data-to-parameter ratio = 14.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 400 Deg.
Alert level G PLAT804_ALERT_5_G ARU-Pack Problem in PLATON Analysis ............ 4 Times
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
The title compound (I) was synthesized according to the literature procedure (Thurston et al., 1996). A mixture of 200 mg of the title compound and 10 ml water was stirred for 1 h and then heated to 413 K for 2 d. Single crystals of (I) suitable for X-ray analysis were obtained after they are cooled to room temperature at 10 oC/h.
Single crystals of (I) suitable for X-ray analysis were obtained by recrystallized under autogenous pressure.
All H atoms were positioned geometrically and refined as riding [C—H = 0.93–0.97 Å, O—H = 0.82 Å]. For CH and CH2 groups, Uiso(H) values were set equal to 1.2Ueq(carrier atom) and for the methyl and hydroxy groups they were set equal to 1.5Ueq(carrier atom).
The oxygen atoms of carboxyl group can coordinate to metal ions forming various complexes with novel structures. In this paper we synthesize a special flexible ligand containing double aromatic acid connected by propyl spacer. Under nitrogen atmosphere we first made the title compound (I). The single crystals of (I) were obtained and its molecular and crystal structures were characterized by single-crystal X-ray diffraction.
The molecular structure of (I) and the atom-numbering scheme are shown in Fig. 1. The dihedral angle between the two benzene ring is 96.3 (3)°, indicating that the two benzene rings are approximately perpendicular to each other. The two methoxy groups are nearly planar with their benzene rings (C2–C7) and (C12–C17) with the r.m.s deviations of 0.0397 (3) and 0.255 (3) Å, respectively. Similarly, two r.m.s deviations of the two carbonyl groups from these two benzene rings are 0.0111 and 0.07233) Å, respectively. The intermolecular O—H···O hydrogen-bonded between the hydroxyl and carbonyl groups form a centrosymmetric dimer (Table 2) and stabilize the crystal structure.
For related literature, see: Thurston et al. (1996).
Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Bruker, 1997).
Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 35% probability level. |
C19H20O8 | Z = 2 |
Mr = 376.35 | F(000) = 396 |
Triclinic, P1 | Dx = 1.415 Mg m−3 |
Hall symbol: -P 1 | Melting point: 512 K |
a = 4.8729 (11) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.9736 (18) Å | Cell parameters from 1045 reflections |
c = 23.604 (6) Å | θ = 2.6–26.0° |
α = 93.744 (4)° | µ = 0.11 mm−1 |
β = 94.260 (4)° | T = 294 K |
γ = 104.173 (4)° | Plate, colourless |
V = 883.4 (3) Å3 | 0.16 × 0.12 × 0.08 mm |
Bruker SMART 1000 CCD area-detector diffractometer | 3537 independent reflections |
Radiation source: fine-focus sealed tube | 1907 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
φ and ω scans | θmax = 26.4°, θmin = 0.9° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −6→4 |
Tmin = 0.982, Tmax = 0.991 | k = −9→9 |
5097 measured reflections | l = −29→28 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0482P)2 + 0.2554P] where P = (Fo2 + 2Fc2)/3 |
3537 reflections | (Δ/σ)max < 0.001 |
248 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C19H20O8 | γ = 104.173 (4)° |
Mr = 376.35 | V = 883.4 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 4.8729 (11) Å | Mo Kα radiation |
b = 7.9736 (18) Å | µ = 0.11 mm−1 |
c = 23.604 (6) Å | T = 294 K |
α = 93.744 (4)° | 0.16 × 0.12 × 0.08 mm |
β = 94.260 (4)° |
Bruker SMART 1000 CCD area-detector diffractometer | 3537 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | 1907 reflections with I > 2σ(I) |
Tmin = 0.982, Tmax = 0.991 | Rint = 0.025 |
5097 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.21 e Å−3 |
3537 reflections | Δρmin = −0.20 e Å−3 |
248 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 | ||
O1 | 1.3675 (5) | 1.0676 (3) | 0.43874 (9) | 0.0579 (6) | |
H1 | 1.4940 | 1.0828 | 0.4649 | 0.087* | |
O2 | 1.1815 (4) | 0.8428 (3) | 0.48774 (8) | 0.0556 (6) | |
O3 | 0.2594 (5) | 0.5435 (3) | 0.36351 (8) | 0.0546 (6) | |
O4 | 0.2585 (4) | 0.7219 (2) | 0.27527 (8) | 0.0449 (5) | |
O5 | −0.1359 (4) | 1.0118 (2) | 0.17115 (7) | 0.0389 (5) | |
O6 | −0.3414 (5) | 1.2372 (2) | 0.22523 (7) | 0.0497 (6) | |
O7 | −0.8275 (4) | 1.5175 (3) | 0.07122 (8) | 0.0505 (6) | |
H7 | −0.9377 | 1.5530 | 0.0500 | 0.076* | |
O8 | −0.8096 (4) | 1.3542 (3) | −0.00843 (8) | 0.0476 (5) | |
C1 | 1.1723 (7) | 0.9327 (4) | 0.44555 (12) | 0.0441 (7) | |
C2 | 0.9296 (6) | 0.8816 (4) | 0.40125 (11) | 0.0419 (7) | |
C3 | 0.9210 (6) | 0.9787 (4) | 0.35512 (11) | 0.0432 (7) | |
H3 | 1.0660 | 1.0776 | 0.3525 | 0.052* | |
C4 | 0.6972 (6) | 0.9293 (4) | 0.31276 (11) | 0.0426 (7) | |
H4 | 0.6922 | 0.9957 | 0.2819 | 0.051* | |
C5 | 0.4823 (6) | 0.7825 (4) | 0.31606 (11) | 0.0379 (7) | |
C6 | 0.4849 (6) | 0.6843 (4) | 0.36349 (11) | 0.0410 (7) | |
C7 | 0.7098 (7) | 0.7356 (4) | 0.40541 (11) | 0.0438 (7) | |
H7A | 0.7141 | 0.6713 | 0.4368 | 0.053* | |
C8 | 0.2343 (9) | 0.4518 (4) | 0.41381 (14) | 0.0752 (11) | |
H8A | 0.3895 | 0.3982 | 0.4189 | 0.113* | |
H8B | 0.0578 | 0.3642 | 0.4100 | 0.113* | |
H8C | 0.2386 | 0.5317 | 0.4463 | 0.113* | |
C9 | 0.2334 (6) | 0.8329 (4) | 0.23078 (11) | 0.0405 (7) | |
H9A | 0.4022 | 0.8533 | 0.2103 | 0.049* | |
H9B | 0.2139 | 0.9440 | 0.2469 | 0.049* | |
C10 | −0.0230 (6) | 0.7462 (3) | 0.19106 (11) | 0.0401 (7) | |
H10A | −0.1880 | 0.7192 | 0.2126 | 0.048* | |
H10B | 0.0028 | 0.6378 | 0.1740 | 0.048* | |
C11 | −0.0767 (6) | 0.8586 (3) | 0.14434 (11) | 0.0408 (7) | |
H11A | 0.0891 | 0.8903 | 0.1232 | 0.049* | |
H11B | −0.2370 | 0.7962 | 0.1180 | 0.049* | |
C12 | −0.2660 (5) | 1.1086 (3) | 0.13794 (11) | 0.0332 (6) | |
C13 | −0.2889 (6) | 1.0933 (3) | 0.07897 (11) | 0.0378 (7) | |
H13 | −0.2030 | 1.0179 | 0.0595 | 0.045* | |
C14 | −0.4406 (6) | 1.1908 (3) | 0.04883 (11) | 0.0386 (7) | |
H14 | −0.4568 | 1.1795 | 0.0092 | 0.046* | |
C15 | −0.5676 (5) | 1.3045 (3) | 0.07725 (11) | 0.0350 (6) | |
C16 | −0.5356 (6) | 1.3250 (3) | 0.13690 (11) | 0.0363 (7) | |
H16 | −0.6171 | 1.4033 | 0.1562 | 0.044* | |
C17 | −0.3841 (6) | 1.2299 (3) | 0.16731 (10) | 0.0347 (6) | |
C18 | −0.7436 (6) | 1.3963 (3) | 0.04375 (12) | 0.0374 (7) | |
C19 | −0.4814 (8) | 1.3418 (4) | 0.25887 (12) | 0.0677 (11) | |
H19A | −0.4077 | 1.4619 | 0.2530 | 0.102* | |
H19B | −0.4482 | 1.3251 | 0.2985 | 0.102* | |
H19C | −0.6820 | 1.3082 | 0.2476 | 0.102* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0599 (15) | 0.0580 (14) | 0.0537 (14) | 0.0173 (12) | −0.0168 (11) | 0.0046 (11) |
O2 | 0.0698 (15) | 0.0620 (14) | 0.0390 (12) | 0.0269 (12) | −0.0092 (11) | 0.0106 (11) |
O3 | 0.0666 (15) | 0.0452 (12) | 0.0504 (13) | 0.0107 (11) | −0.0021 (11) | 0.0133 (10) |
O4 | 0.0524 (13) | 0.0423 (11) | 0.0416 (12) | 0.0164 (10) | −0.0068 (10) | 0.0100 (9) |
O5 | 0.0462 (12) | 0.0398 (11) | 0.0343 (10) | 0.0204 (9) | −0.0055 (9) | 0.0026 (8) |
O6 | 0.0782 (15) | 0.0501 (12) | 0.0278 (10) | 0.0310 (11) | −0.0003 (10) | 0.0019 (9) |
O7 | 0.0586 (15) | 0.0558 (13) | 0.0449 (12) | 0.0321 (11) | −0.0064 (10) | 0.0055 (10) |
O8 | 0.0520 (13) | 0.0617 (13) | 0.0338 (11) | 0.0253 (11) | −0.0035 (10) | 0.0056 (10) |
C1 | 0.053 (2) | 0.0454 (19) | 0.0386 (17) | 0.0252 (17) | −0.0026 (15) | −0.0010 (14) |
C2 | 0.0489 (19) | 0.0464 (18) | 0.0355 (16) | 0.0242 (15) | −0.0009 (14) | 0.0001 (13) |
C3 | 0.0466 (19) | 0.0475 (18) | 0.0380 (17) | 0.0170 (15) | 0.0011 (14) | 0.0053 (14) |
C4 | 0.052 (2) | 0.0465 (18) | 0.0333 (16) | 0.0204 (16) | 0.0000 (14) | 0.0073 (13) |
C5 | 0.0439 (18) | 0.0413 (16) | 0.0327 (15) | 0.0211 (14) | −0.0020 (13) | 0.0010 (13) |
C6 | 0.051 (2) | 0.0372 (16) | 0.0376 (17) | 0.0177 (15) | 0.0023 (14) | 0.0026 (13) |
C7 | 0.061 (2) | 0.0452 (18) | 0.0338 (16) | 0.0292 (17) | 0.0024 (15) | 0.0082 (13) |
C8 | 0.111 (3) | 0.053 (2) | 0.060 (2) | 0.014 (2) | 0.004 (2) | 0.0254 (18) |
C9 | 0.0412 (18) | 0.0460 (17) | 0.0377 (16) | 0.0174 (14) | −0.0025 (13) | 0.0093 (13) |
C10 | 0.0467 (18) | 0.0359 (16) | 0.0402 (16) | 0.0178 (14) | −0.0028 (14) | 0.0011 (13) |
C11 | 0.0451 (18) | 0.0413 (16) | 0.0376 (16) | 0.0180 (14) | −0.0047 (13) | −0.0027 (13) |
C12 | 0.0297 (15) | 0.0353 (15) | 0.0342 (15) | 0.0081 (12) | −0.0026 (12) | 0.0070 (12) |
C13 | 0.0388 (17) | 0.0441 (16) | 0.0334 (16) | 0.0161 (14) | 0.0028 (13) | 0.0033 (13) |
C14 | 0.0377 (17) | 0.0506 (17) | 0.0271 (14) | 0.0119 (14) | −0.0029 (13) | 0.0044 (13) |
C15 | 0.0316 (16) | 0.0383 (15) | 0.0358 (16) | 0.0103 (13) | 0.0001 (12) | 0.0054 (12) |
C16 | 0.0411 (17) | 0.0331 (15) | 0.0353 (16) | 0.0112 (13) | 0.0009 (13) | 0.0031 (12) |
C17 | 0.0408 (17) | 0.0341 (15) | 0.0293 (15) | 0.0094 (13) | 0.0016 (13) | 0.0046 (12) |
C18 | 0.0364 (17) | 0.0370 (16) | 0.0402 (17) | 0.0120 (13) | −0.0002 (14) | 0.0066 (13) |
C19 | 0.120 (3) | 0.056 (2) | 0.0395 (18) | 0.042 (2) | 0.020 (2) | 0.0039 (16) |
O1—C1 | 1.277 (3) | C8—H8A | 0.9600 |
O1—H1 | 0.8200 | C8—H8B | 0.9600 |
O2—C1 | 1.269 (3) | C8—H8C | 0.9600 |
O3—C6 | 1.365 (3) | C9—C10 | 1.495 (4) |
O3—C8 | 1.432 (3) | C9—H9A | 0.9700 |
O4—C5 | 1.369 (3) | C9—H9B | 0.9700 |
O4—C9 | 1.434 (3) | C10—C11 | 1.513 (3) |
O5—C12 | 1.363 (3) | C10—H10A | 0.9700 |
O5—C11 | 1.441 (3) | C10—H10B | 0.9700 |
O6—C17 | 1.363 (3) | C11—H11A | 0.9700 |
O6—C19 | 1.437 (3) | C11—H11B | 0.9700 |
O7—C18 | 1.294 (3) | C12—C13 | 1.383 (3) |
O7—H7 | 0.8200 | C12—C17 | 1.411 (3) |
O8—C18 | 1.252 (3) | C13—C14 | 1.390 (3) |
C1—C2 | 1.477 (4) | C13—H13 | 0.9300 |
C2—C3 | 1.380 (4) | C14—C15 | 1.383 (4) |
C2—C7 | 1.390 (4) | C14—H14 | 0.9300 |
C3—C4 | 1.386 (4) | C15—C16 | 1.399 (3) |
C3—H3 | 0.9300 | C15—C18 | 1.476 (3) |
C4—C5 | 1.377 (4) | C16—C17 | 1.379 (3) |
C4—H4 | 0.9300 | C16—H16 | 0.9300 |
C5—C6 | 1.408 (4) | C19—H19A | 0.9600 |
C6—C7 | 1.384 (4) | C19—H19B | 0.9600 |
C7—H7A | 0.9300 | C19—H19C | 0.9600 |
C1—O1—H1 | 109.5 | C9—C10—C11 | 112.2 (2) |
C6—O3—C8 | 117.7 (2) | C9—C10—H10A | 109.2 |
C5—O4—C9 | 116.2 (2) | C11—C10—H10A | 109.2 |
C12—O5—C11 | 117.88 (19) | C9—C10—H10B | 109.2 |
C17—O6—C19 | 118.7 (2) | C11—C10—H10B | 109.2 |
C18—O7—H7 | 109.5 | H10A—C10—H10B | 107.9 |
O2—C1—O1 | 122.9 (3) | O5—C11—C10 | 107.4 (2) |
O2—C1—C2 | 120.0 (3) | O5—C11—H11A | 110.2 |
O1—C1—C2 | 117.1 (3) | C10—C11—H11A | 110.2 |
C3—C2—C7 | 119.6 (3) | O5—C11—H11B | 110.2 |
C3—C2—C1 | 119.9 (3) | C10—C11—H11B | 110.2 |
C7—C2—C1 | 120.5 (3) | H11A—C11—H11B | 108.5 |
C2—C3—C4 | 120.2 (3) | O5—C12—C13 | 124.3 (2) |
C2—C3—H3 | 119.9 | O5—C12—C17 | 115.9 (2) |
C4—C3—H3 | 119.9 | C13—C12—C17 | 119.8 (2) |
C5—C4—C3 | 120.4 (3) | C12—C13—C14 | 120.0 (3) |
C5—C4—H4 | 119.8 | C12—C13—H13 | 120.0 |
C3—C4—H4 | 119.8 | C14—C13—H13 | 120.0 |
O4—C5—C4 | 124.1 (2) | C15—C14—C13 | 120.6 (2) |
O4—C5—C6 | 115.9 (3) | C15—C14—H14 | 119.7 |
C4—C5—C6 | 120.0 (3) | C13—C14—H14 | 119.7 |
O3—C6—C7 | 125.5 (3) | C14—C15—C16 | 119.5 (2) |
O3—C6—C5 | 115.6 (3) | C14—C15—C18 | 118.9 (2) |
C7—C6—C5 | 118.8 (3) | C16—C15—C18 | 121.6 (2) |
C6—C7—C2 | 120.9 (3) | C17—C16—C15 | 120.4 (2) |
C6—C7—H7A | 119.5 | C17—C16—H16 | 119.8 |
C2—C7—H7A | 119.5 | C15—C16—H16 | 119.8 |
O3—C8—H8A | 109.5 | O6—C17—C16 | 125.7 (2) |
O3—C8—H8B | 109.5 | O6—C17—C12 | 114.7 (2) |
H8A—C8—H8B | 109.5 | C16—C17—C12 | 119.6 (2) |
O3—C8—H8C | 109.5 | O8—C18—O7 | 122.9 (2) |
H8A—C8—H8C | 109.5 | O8—C18—C15 | 120.4 (2) |
H8B—C8—H8C | 109.5 | O7—C18—C15 | 116.7 (2) |
O4—C9—C10 | 108.4 (2) | O6—C19—H19A | 109.5 |
O4—C9—H9A | 110.0 | O6—C19—H19B | 109.5 |
C10—C9—H9A | 110.0 | H19A—C19—H19B | 109.5 |
O4—C9—H9B | 110.0 | O6—C19—H19C | 109.5 |
C10—C9—H9B | 110.0 | H19A—C19—H19C | 109.5 |
H9A—C9—H9B | 108.4 | H19B—C19—H19C | 109.5 |
O2—C1—C2—C3 | −179.4 (2) | C12—O5—C11—C10 | −162.3 (2) |
O1—C1—C2—C3 | −0.1 (4) | C9—C10—C11—O5 | −63.3 (3) |
O2—C1—C2—C7 | 0.1 (4) | C11—O5—C12—C13 | −14.9 (4) |
O1—C1—C2—C7 | 179.5 (3) | C11—O5—C12—C17 | 164.6 (2) |
C7—C2—C3—C4 | −1.0 (4) | O5—C12—C13—C14 | 176.1 (2) |
C1—C2—C3—C4 | 178.5 (2) | C17—C12—C13—C14 | −3.3 (4) |
C2—C3—C4—C5 | −0.4 (4) | C12—C13—C14—C15 | 0.5 (4) |
C9—O4—C5—C4 | −8.3 (4) | C13—C14—C15—C16 | 1.9 (4) |
C9—O4—C5—C6 | 171.9 (2) | C13—C14—C15—C18 | −175.7 (2) |
C3—C4—C5—O4 | −177.9 (2) | C14—C15—C16—C17 | −1.5 (4) |
C3—C4—C5—C6 | 1.8 (4) | C18—C15—C16—C17 | 176.1 (2) |
C8—O3—C6—C7 | 7.6 (4) | C19—O6—C17—C16 | 5.1 (4) |
C8—O3—C6—C5 | −172.6 (2) | C19—O6—C17—C12 | −172.9 (3) |
O4—C5—C6—O3 | −1.7 (3) | C15—C16—C17—O6 | −179.2 (2) |
C4—C5—C6—O3 | 178.5 (2) | C15—C16—C17—C12 | −1.3 (4) |
O4—C5—C6—C7 | 178.0 (2) | O5—C12—C17—O6 | 2.4 (3) |
C4—C5—C6—C7 | −1.7 (4) | C13—C12—C17—O6 | −178.2 (2) |
O3—C6—C7—C2 | −180.0 (3) | O5—C12—C17—C16 | −175.8 (2) |
C5—C6—C7—C2 | 0.3 (4) | C13—C12—C17—C16 | 3.7 (4) |
C3—C2—C7—C6 | 1.1 (4) | C14—C15—C18—O8 | 9.9 (4) |
C1—C2—C7—C6 | −178.5 (2) | C16—C15—C18—O8 | −167.6 (2) |
C5—O4—C9—C10 | −179.4 (2) | C14—C15—C18—O7 | −171.3 (2) |
O4—C9—C10—C11 | 176.8 (2) | C16—C15—C18—O7 | 11.2 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.82 | 1.81 | 2.618 (3) | 166 |
O7—H7···O8ii | 0.82 | 1.84 | 2.658 (3) | 174 |
Symmetry codes: (i) −x+3, −y+2, −z+1; (ii) −x−2, −y+3, −z. |
Experimental details
Crystal data | |
Chemical formula | C19H20O8 |
Mr | 376.35 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 294 |
a, b, c (Å) | 4.8729 (11), 7.9736 (18), 23.604 (6) |
α, β, γ (°) | 93.744 (4), 94.260 (4), 104.173 (4) |
V (Å3) | 883.4 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.16 × 0.12 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART 1000 CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.982, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5097, 3537, 1907 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.135, 0.99 |
No. of reflections | 3537 |
No. of parameters | 248 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.20 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.82 | 1.81 | 2.618 (3) | 165.9 |
O7—H7···O8ii | 0.82 | 1.84 | 2.658 (3) | 174.4 |
Symmetry codes: (i) −x+3, −y+2, −z+1; (ii) −x−2, −y+3, −z. |
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The oxygen atoms of carboxyl group can coordinate to metal ions forming various complexes with novel structures. In this paper we synthesize a special flexible ligand containing double aromatic acid connected by propyl spacer. Under nitrogen atmosphere we first made the title compound (I). The single crystals of (I) were obtained and its molecular and crystal structures were characterized by single-crystal X-ray diffraction.
The molecular structure of (I) and the atom-numbering scheme are shown in Fig. 1. The dihedral angle between the two benzene ring is 96.3 (3)°, indicating that the two benzene rings are approximately perpendicular to each other. The two methoxy groups are nearly planar with their benzene rings (C2–C7) and (C12–C17) with the r.m.s deviations of 0.0397 (3) and 0.255 (3) Å, respectively. Similarly, two r.m.s deviations of the two carbonyl groups from these two benzene rings are 0.0111 and 0.07233) Å, respectively. The intermolecular O—H···O hydrogen-bonded between the hydroxyl and carbonyl groups form a centrosymmetric dimer (Table 2) and stabilize the crystal structure.