Literature DB >> 21579628

Poly[[di-μ-aqua-(μ-4-formyl-2-meth-oxy-phenol-ato)disodium] 4-formyl-2-meth-oxy-phenolate].

Muhammad Nadeem Asghar, Onur Sahin, Muhammad Nadeem Arshad, Uzma Mazhar, Islam Ullah Khan, Orhan Büyükgüngör.   

Abstract

In the title coordination polymer, {[Na(2)(C(8)H(7)O(3))(H(2)O)(4)](C(8)H(7)O(3))}(n), all the non-H atoms except the water O atoms lie on a crystallographic mirror plane. One sodium cation is bonded to four water O atoms and one vanillinate O atom in a distorted square-based pyramidal arrangement; the other Na(+) ion is six-coordinated by four water O atoms and two vanillinate O atoms in an irregular geometry. One of the vanillinate anions is directly bonded to two sodium ions, whilst the other only inter-acts with the polymeric network by way of hydrogen bonds. In the crystal, a two-dimensional polymeric array is formed; this is reinforced by O-H⋯O hydrogen bonds, which generate R(2) (1)(6) and R(2) (2)(20) loops.

Entities:  

Year:  2010        PMID： 21579628      PMCID： PMC2979829          DOI： 10.1107/S1600536810000711

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For related crystal structures, see: Velavan et al. (1995 ▶); Iwasaki (1973 ▶); Iwasaki et al. (1976 ▶); Usman et al. (2002 ▶); Li et al. (1999 ▶); Kaduk (2000 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

[Na2(C8H7O3)(H2O)4](C8H7O3) M = 420.32 Orthorhombic, a = 12.2281 (6) Å b = 6.7681 (3) Å c = 22.6734 (10) Å V = 1876.47 (15) Å3 Z = 4 Mo Kα radiation μ = 0.16 mm−1 T = 296 K 0.42 × 0.33 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.938, T max = 0.962 10469 measured reflections 2121 independent reflections 1825 reflections with I > 2σ(I) R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.044 wR(F 2) = 0.119 S = 1.07 2121 reflections 180 parameters 12 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.63 e Å−3 Δρmin = −0.67 e Å−3 Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and SHELXL97. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810000711/hb5277sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000711/hb5277Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Na2(C8H7O3)(H2O)4](C8H7O3)F(000) = 880
Mr = 420.32Dx = 1.488 Mg m−3
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 5113 reflections
a = 12.2281 (6) Åθ = 3.0–31.1°
b = 6.7681 (3) ŵ = 0.16 mm−1
c = 22.6734 (10) ÅT = 296 K
V = 1876.47 (15) Å3Block, colourles
Z = 40.42 × 0.33 × 0.24 mm
Bruker APEXII CCD diffractometer2121 independent reflections
Radiation source: fine-focus sealed tube1825 reflections with I > 2σ(I)
graphiteRint = 0.020
phi and ω scansθmax = 26.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2007)h = −15→15
Tmin = 0.938, Tmax = 0.962k = −8→4
10469 measured reflectionsl = −19→28
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.119w = 1/[σ2(Fo2) + (0.0476P)2 + 1.7283P] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
2121 reflectionsΔρmax = 0.63 e Å−3
180 parametersΔρmin = −0.67 e Å−3
12 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0138 (14)
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.
xyzUiso*/UeqOcc. (<1)
C10.6494 (2)0.75000.97772 (12)0.0327 (7)
C20.7164 (2)0.75000.92725 (13)0.0321 (7)
H20.79200.75000.93150.039*
C30.6713 (2)0.75000.87213 (12)0.0263 (6)
C40.5554 (2)0.75000.86488 (12)0.0260 (6)
C50.4908 (2)0.75000.91595 (13)0.0317 (7)
H50.41510.75000.91230.038*
C60.5368 (2)0.75000.97117 (13)0.0331 (7)
H60.49210.75001.00440.040*
C70.6978 (3)0.75001.03533 (14)0.0505 (10)
H70.77380.75001.03700.061*
C80.8444 (2)0.75000.82464 (14)0.0345 (7)
H8A0.87570.72140.78680.052*0.50
H8B0.86690.65120.85250.052*0.50
H8C0.86890.87740.83770.052*0.50
C90.6086 (3)0.75000.49146 (15)0.0582 (12)
C100.7012 (2)0.75000.45577 (13)0.0318 (7)
H100.77040.75000.47280.038*
C110.6907 (2)0.75000.39567 (12)0.0258 (6)
C120.5862 (2)0.75000.36734 (13)0.0336 (7)
C130.4958 (3)0.75000.40446 (17)0.092 (2)
H130.42600.75000.38820.111*
C140.5076 (3)0.75000.46474 (18)0.099 (2)
H140.44520.75000.48820.118*
C150.6143 (3)0.75000.55467 (17)0.0725 (15)
H150.54770.75000.57450.087*
C160.8841 (2)0.75000.38079 (14)0.0364 (7)
H16A0.89620.87100.40190.055*0.50
H16B0.93640.73890.34940.055*0.50
H16C0.89220.64010.40720.055*0.50
O10.59561 (12)0.4859 (3)0.73010 (7)0.0386 (4)
H1A0.5721 (19)0.552 (4)0.7574 (10)0.047 (8)*
H1B0.5423 (18)0.426 (4)0.7162 (11)0.060 (9)*
O20.83431 (12)0.4956 (3)0.68524 (7)0.0353 (4)
H2A0.835 (2)0.439 (4)0.6534 (9)0.047 (8)*
H2B0.8935 (17)0.557 (4)0.6870 (11)0.051 (8)*
O30.72906 (16)0.75000.82013 (9)0.0352 (5)
O40.6492 (2)0.75001.08231 (10)0.0528 (7)
O50.51190 (16)0.75000.81191 (8)0.0319 (5)
O60.6945 (2)0.75000.58503 (11)0.0611 (8)
O70.77607 (16)0.75000.35679 (9)0.0367 (5)
O80.57840 (16)0.75000.31048 (8)0.0325 (5)
Na10.69720 (10)0.75000.68819 (5)0.0353 (3)
Na20.75745 (10)0.25000.75268 (5)0.0343 (3)
U11U22U33U12U13U23
C10.0341 (15)0.0405 (18)0.0234 (14)0.000−0.0004 (11)0.000
C20.0253 (13)0.0429 (18)0.0282 (14)0.000−0.0014 (11)0.000
C30.0260 (13)0.0284 (15)0.0245 (13)0.0000.0031 (10)0.000
C40.0265 (13)0.0271 (15)0.0245 (13)0.000−0.0018 (10)0.000
C50.0241 (13)0.0400 (17)0.0309 (15)0.0000.0014 (11)0.000
C60.0322 (14)0.0404 (18)0.0268 (14)0.0000.0053 (11)0.000
C70.0400 (17)0.084 (3)0.0279 (16)0.000−0.0038 (13)0.000
C80.0274 (14)0.0409 (18)0.0352 (16)0.0000.0065 (12)0.000
C90.0366 (17)0.110 (4)0.0276 (17)0.0000.0020 (13)0.000
C100.0299 (14)0.0375 (17)0.0281 (14)0.000−0.0045 (11)0.000
C110.0268 (13)0.0240 (14)0.0267 (13)0.0000.0007 (10)0.000
C120.0295 (14)0.0457 (19)0.0256 (14)0.000−0.0029 (11)0.000
C130.0249 (16)0.219 (7)0.0333 (18)0.000−0.0012 (14)0.000
C140.0368 (19)0.218 (6)0.041 (2)0.0000.0087 (17)0.000
C150.047 (2)0.138 (5)0.0322 (19)0.0000.0065 (16)0.000
C160.0245 (13)0.0486 (19)0.0363 (16)0.000−0.0056 (12)0.000
O10.0325 (8)0.0420 (10)0.0413 (9)−0.0063 (7)0.0053 (7)−0.0109 (8)
O20.0347 (8)0.0402 (9)0.0311 (8)−0.0032 (7)0.0039 (6)−0.0014 (7)
O30.0256 (10)0.0557 (15)0.0243 (10)0.0000.0028 (8)0.000
O40.0623 (16)0.0727 (19)0.0233 (11)0.000−0.0007 (10)0.000
O50.0266 (9)0.0442 (13)0.0249 (10)0.000−0.0030 (8)0.000
O60.0559 (16)0.099 (2)0.0287 (12)0.000−0.0051 (11)0.000
O70.0243 (10)0.0597 (15)0.0262 (10)0.000−0.0024 (8)0.000
O80.0291 (10)0.0442 (13)0.0242 (10)0.000−0.0039 (8)0.000
Na10.0336 (6)0.0352 (7)0.0371 (7)0.0000.0020 (5)0.000
Na20.0337 (6)0.0422 (7)0.0272 (6)0.0000.0001 (5)0.000
C1—C61.385 (4)C12—C131.390 (5)
C1—C21.407 (4)C13—C141.374 (6)
C1—C71.434 (4)C13—H130.9300
C2—C31.366 (4)C14—H140.9300
C2—H20.9300C15—O61.198 (5)
C3—O31.374 (3)C15—H150.9300
C3—C41.427 (4)C16—O71.428 (3)
C4—O51.314 (3)C16—H16A0.9600
C4—C51.402 (4)C16—H16B0.9600
C5—C61.372 (4)C16—H16C0.9600
C5—H50.9300O1—H1A0.817 (17)
C6—H60.9300O1—H1B0.830 (17)
C7—O41.220 (4)O2—H2A0.816 (17)
C7—H70.9300O2—H2B0.836 (17)
C8—O31.414 (3)Na1—O12.3751 (18)
C8—H8A0.9600Na1—O22.4043 (18)
C8—H8B0.9600Na1—O62.339 (3)
C8—H8C0.9600Na1—O1i2.3751 (18)
C9—C141.376 (5)Na1—O2i2.4043 (18)
C9—C101.391 (4)Na2—O12.5938 (19)
C9—C151.435 (5)Na2—O22.4462 (18)
C10—C111.369 (4)Na2—O2ii2.4462 (18)
C10—H100.9300Na2—O1ii2.5938 (19)
C11—O71.366 (3)Na2—O7iii2.396 (2)
C11—C121.430 (4)Na2—O8iii2.397 (2)
C12—O81.293 (3)
C6—C1—C2119.4 (3)H16A—C16—H16C109.5
C6—C1—C7120.6 (3)H16B—C16—H16C109.5
C2—C1—C7120.0 (3)Na1—O1—Na298.23 (6)
C3—C2—C1120.6 (3)Na1—O1—H1A94.3 (19)
C3—C2—H2119.7Na2—O1—H1A117.2 (19)
C1—C2—H2119.7Na1—O1—H1B129 (2)
C2—C3—O3125.3 (2)Na2—O1—H1B112 (2)
C2—C3—C4120.4 (2)H1A—O1—H1B106 (2)
O3—C3—C4114.3 (2)Na1—O2—Na2101.61 (6)
O5—C4—C5121.8 (2)Na1—O2—H2A111.6 (19)
O5—C4—C3120.5 (2)Na2—O2—H2A104.0 (19)
C5—C4—C3117.7 (2)Na1—O2—H2B104.2 (19)
C6—C5—C4121.5 (3)Na2—O2—H2B129.9 (19)
C6—C5—H5119.2H2A—O2—H2B105 (2)
C4—C5—H5119.2C3—O3—C8116.8 (2)
C5—C6—C1120.3 (3)C3—O3—Na1141.66 (16)
C5—C6—H6119.8C8—O3—Na1101.57 (16)
C1—C6—H6119.8C15—O6—Na1125.9 (3)
O4—C7—C1126.4 (3)C11—O7—C16117.4 (2)
O4—C7—H7116.8C11—O7—Na2iv120.33 (16)
C1—C7—H7116.8C16—O7—Na2iv122.24 (17)
O3—C8—H8A109.5C12—O8—Na2iv118.88 (18)
O3—C8—H8B109.5O6—Na1—O1i113.13 (7)
H8A—C8—H8B109.5O6—Na1—O1113.13 (7)
O3—C8—H8C109.5O1i—Na1—O197.63 (9)
H8A—C8—H8C109.5O6—Na1—O2i88.96 (7)
H8B—C8—H8C109.5O1i—Na1—O2i80.61 (6)
C14—C9—C10118.3 (3)O1—Na1—O2i156.19 (8)
C14—C9—C15118.9 (4)O6—Na1—O288.96 (7)
C10—C9—C15122.8 (3)O1i—Na1—O2156.19 (8)
C11—C10—C9120.2 (3)O1—Na1—O280.61 (5)
C11—C10—H10119.9O2i—Na1—O291.48 (9)
C9—C10—H10119.9O6—Na1—O3173.38 (9)
O7—C11—C10124.8 (3)O1i—Na1—O370.78 (5)
O7—C11—C12113.1 (2)O1—Na1—O370.78 (5)
C10—C11—C12122.1 (3)O2i—Na1—O386.42 (5)
O8—C12—C13123.0 (3)O2—Na1—O386.42 (5)
O8—C12—C11120.9 (3)O7iii—Na2—O8iii66.71 (7)
C13—C12—C11116.0 (3)O7iii—Na2—O2ii132.97 (5)
C14—C13—C12121.3 (3)O8iii—Na2—O2ii91.15 (6)
C14—C13—H13119.4O7iii—Na2—O2132.97 (5)
C12—C13—H13119.4O8iii—Na2—O291.15 (6)
C13—C14—C9122.1 (4)O2ii—Na2—O285.60 (9)
C13—C14—H14118.9O7iii—Na2—O1ii93.66 (6)
C9—C14—H14118.9O8iii—Na2—O1ii138.31 (5)
O6—C15—C9127.8 (4)O2ii—Na2—O1ii75.61 (6)
O6—C15—H15116.1O2—Na2—O1ii126.01 (7)
C9—C15—H15116.1O7iii—Na2—O193.66 (6)
O7—C16—H16A109.5O8iii—Na2—O1138.31 (5)
O7—C16—H16B109.5O2ii—Na2—O1126.01 (7)
H16A—C16—H16B109.5O2—Na2—O175.61 (5)
O7—C16—H16C109.5O1ii—Na2—O175.98 (8)
C6—C1—C2—C30.000 (2)C10—C11—O7—Na2iv180.0
C7—C1—C2—C3180.000 (1)C12—C11—O7—Na2iv0.0
C1—C2—C3—O3180.000 (1)C13—C12—O8—Na2iv180.0
C1—C2—C3—C40.000 (1)C11—C12—O8—Na2iv0.0
C2—C3—C4—O5180.000 (1)C15—O6—Na1—O1i−54.92 (6)
O3—C3—C4—O50.000 (1)C15—O6—Na1—O154.92 (6)
C2—C3—C4—C50.000 (1)C15—O6—Na1—O2i−134.25 (4)
O3—C3—C4—C5180.000 (1)C15—O6—Na1—O2134.25 (4)
O5—C4—C5—C6180.000 (1)Na2—O1—Na1—O699.60 (9)
C3—C4—C5—C60.000 (2)Na2—O1—Na1—O1i−141.19 (5)
C4—C5—C6—C10.000 (2)Na2—O1—Na1—O2i−57.16 (18)
C2—C1—C6—C50.000 (2)Na2—O1—Na1—O214.80 (6)
C7—C1—C6—C5180.000 (1)Na2—O1—Na1—O3−74.67 (6)
C6—C1—C7—O40.000 (2)Na2—O2—Na1—O6−129.53 (7)
C2—C1—C7—O4180.000 (2)Na2—O2—Na1—O1i71.75 (18)
C14—C9—C10—C110.0Na2—O2—Na1—O1−15.88 (7)
C15—C9—C10—C11180.0Na2—O2—Na1—O2i141.54 (5)
C9—C10—C11—O7180.0Na2—O2—Na1—O355.22 (6)
C9—C10—C11—C120.0C3—O3—Na1—O1i52.85 (5)
O7—C11—C12—O80.0C8—O3—Na1—O1i−127.15 (5)
C10—C11—C12—O8180.0C3—O3—Na1—O1−52.85 (5)
O7—C11—C12—C13180.0C8—O3—Na1—O1127.15 (5)
C10—C11—C12—C130.0C3—O3—Na1—O2i134.14 (4)
O8—C12—C13—C14180.0C8—O3—Na1—O2i−45.86 (4)
C11—C12—C13—C140.0C3—O3—Na1—O2−134.14 (4)
C12—C13—C14—C90.000 (1)C8—O3—Na1—O245.86 (4)
C10—C9—C14—C130.000 (1)Na1—O2—Na2—O7iii−66.66 (11)
C15—C9—C14—C13180.0Na1—O2—Na2—O8iii−125.21 (6)
C14—C9—C15—O6180.0Na1—O2—Na2—O2ii143.73 (5)
C10—C9—C15—O60.000 (1)Na1—O2—Na2—O1ii75.08 (9)
C2—C3—O3—C80.000 (1)Na1—O2—Na2—O114.79 (6)
C4—C3—O3—C8180.000 (1)Na1—O1—Na2—O7iii118.71 (6)
C2—C3—O3—Na1180.000 (1)Na1—O1—Na2—O8iii60.30 (12)
C4—C3—O3—Na10.000 (1)Na1—O1—Na2—O2ii−88.29 (9)
C9—C15—O6—Na1180.0Na1—O1—Na2—O2−14.81 (6)
C10—C11—O7—C160.0Na1—O1—Na2—O1ii−148.42 (4)
C12—C11—O7—C16180.0
D—H···AD—HH···AD···AD—H···A
O1—H1A···O50.82 (2)1.97 (2)2.772 (2)169 (3)
O1—H1B···O8v0.83 (2)1.99 (2)2.815 (2)172 (3)
O2—H2A···O4iv0.82 (2)2.07 (2)2.872 (2)168 (3)
O2—H2B···O5vi0.84 (2)1.95 (2)2.772 (2)168 (3)
Na1—O12.3751 (18)
Na1—O22.4043 (18)
Na1—O62.339 (3)
Na2—O12.5938 (19)
Na2—O22.4462 (18)
Na2—O7i2.396 (2)
Na2—O8i2.397 (2)
O7i—Na2—O193.66 (6)
O8i—Na2—O1138.31 (5)
O2ii—Na2—O1126.01 (7)
O2—Na2—O175.61 (5)
O1ii—Na2—O175.98 (8)

Symmetry codes: (i) ; (ii) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1—H1A⋯O50.82 (2)1.97 (2)2.772 (2)169 (3)
O1—H1B⋯O8iii0.83 (2)1.99 (2)2.815 (2)172 (3)
O2—H2A⋯O4iv0.82 (2)2.07 (2)2.872 (2)168 (3)
O2—H2B⋯O5v0.84 (2)1.95 (2)2.772 (2)168 (3)

Symmetry codes: (iii) ; (iv) ; (v) .

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