Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807035647/bx2099sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807035647/bx2099Isup2.hkl |
CCDC reference: 644749
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.002 Å
- R factor = 0.026
- wR factor = 0.078
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT165_ALERT_3_C Nr. of Status R Flagged Non-Hydrogen Atoms ..... 7 PLAT322_ALERT_2_C Check Hybridisation of H9A in Main Residue . ?
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn1 (2) 2.09 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 6
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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
Glycine (2 mmol, 0.150 g), 3-carboxysalicylaldehyde (2 mmol, 0.336 g) and sodium hydroxide (2 mmol, 0.08 g) were dissolved in 80% aqueous methanol (25 ml). To the clear yellow solution was added an aqueous solution (15 ml) of Zinc(II) nitrate (2 mmol, 0.376 g). The solution was filtered after keeping at 323 K for 6 h. Yellow crystals separated from the solution after two weeks in about 46% yield (according to Zinc).
The C-bound H atoms were placed at calculated positions (C—H = 0.95 Å) and refined as riding, with Uiso(H) = 1.2Ueq(C). The other H atoms were located in a difference Fourier map and refined with O—H distance restraints of 0.85–0.97 Å, and with Uiso(H) values of 1.5Ueq(O).
Schiff bases have been intensively investigated recently owing to their strong coordination capability and diverse biological activities, such as antibacterial, antitumor activities etc (Yang et al., 2000; May et al., 2004). Among these Schiff bases, aminophenol-containing Schiff base have received extraordinatry attention for its' flexible coordination codes. some unusual structures have been synthesized through these ligands, such as helical structures (Ranford et al.,1999;Erxleben,2001).
However, in those reported literatures, Seldom helical structures with the ligand of 3-Carboxysalicylaldehyde have been generated. We have reported two structures derived from the ligand 3-Carboxysalicylideneglycinate(Cai et al.,2006; Cai et al.,2007). As an extension of the work, We report here the preparations and crystal structure characterizations of the title helical coordination polymer(I).
The crystal structure of the title complex(I) is very similar to the former reported structure (Cai et al.,2007).there is one ZnIIatom,one 3-Carboxysalicylideneglycinate anion, one coordinated water molecule and one lattice water molecule in each independent crystallographic unit, Each ZnII atom adapts a square-based pyramidal geometry.It is worthy of mention that the remaining protonated carboxylate group does not participate in coordination, but involve in hydrogen bonding.In the title complex,each pair of adjacent ZnII atom are bridged by a carboxy group of the ligand to form a chiral helical chain running along a crystallographic 21 axis in the b direction with a pitch of 6.873 Å. There are two kinds of hydrogen bonding interactions in the title complex.The acidic H atom forms a strong intramolecular O—H···O hydrogen bond to the phenoxy O atom [O···O = 2.450 (2) Å]. The other hydrogen bonding interactions are involving the carboxylate O atoms and coordinated/uncoordinated water molecules. By which the chains are connected to form a three-dimensional network.
For biological activity, see: Yang et al. (2000); May et al. (2004). For flexible coordination codes, see: Ranford et al. (1999); Erxleben (2001). For synthesis of related compounds, see: Cai et al. (2006, 2007).
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 (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.
[Zn(C10H7NO5)(H2O)]·H2O | F(000) = 656 |
Mr = 322.59 | Dx = 1.890 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 978 reflections |
a = 8.3985 (9) Å | θ = 3.1–27.0° |
b = 6.8730 (7) Å | µ = 2.20 mm−1 |
c = 19.637 (2) Å | T = 173 K |
β = 90.781 (2)° | Block, yellow |
V = 1133.4 (2) Å3 | 0.49 × 0.41 × 0.22 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 2479 independent reflections |
Radiation source: fine-focus sealed tube | 2171 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
Detector resolution: 0 pixels mm-1 | θmax = 27.0°, θmin = 2.4° |
φ and ω scans | h = −10→5 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −7→8 |
Tmin = 0.354, Tmax = 0.617 | l = −24→25 |
5599 measured reflections |
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)] = 0.026 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.078 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0474P)2 + 0.7019P] where P = (Fo2 + 2Fc2)/3 |
2479 reflections | (Δ/σ)max = 0.001 |
166 parameters | Δρmax = 0.84 e Å−3 |
6 restraints | Δρmin = −0.87 e Å−3 |
[Zn(C10H7NO5)(H2O)]·H2O | V = 1133.4 (2) Å3 |
Mr = 322.59 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.3985 (9) Å | µ = 2.20 mm−1 |
b = 6.8730 (7) Å | T = 173 K |
c = 19.637 (2) Å | 0.49 × 0.41 × 0.22 mm |
β = 90.781 (2)° |
Bruker SMART APEX CCD area-detector diffractometer | 2479 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2171 reflections with I > 2σ(I) |
Tmin = 0.354, Tmax = 0.617 | Rint = 0.017 |
5599 measured reflections |
R[F2 > 2σ(F2)] = 0.026 | 6 restraints |
wR(F2) = 0.078 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.84 e Å−3 |
2479 reflections | Δρmin = −0.87 e Å−3 |
166 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 | ||
Zn1 | 0.35846 (3) | 0.11867 (3) | 0.168087 (11) | 0.01598 (10) | |
N1 | 0.5830 (2) | 0.1334 (2) | 0.13345 (9) | 0.0168 (4) | |
O1 | 0.01579 (19) | 0.2942 (3) | −0.09655 (8) | 0.0276 (4) | |
O2 | 0.0220 (2) | 0.2399 (3) | 0.01427 (8) | 0.0299 (4) | |
H2 | 0.108 (4) | 0.227 (5) | 0.0478 (16) | 0.045* | |
O3 | 0.27673 (17) | 0.1979 (2) | 0.07472 (7) | 0.0215 (3) | |
O4 | 0.47631 (17) | −0.0620 (2) | 0.24040 (7) | 0.0194 (3) | |
O5 | 0.71706 (17) | −0.1686 (2) | 0.27122 (7) | 0.0193 (3) | |
O6 | 0.1646 (2) | −0.0488 (3) | 0.17852 (9) | 0.0327 (4) | |
H6A | 0.109 (3) | −0.113 (4) | 0.1510 (11) | 0.049* | |
H6B | 0.117 (3) | −0.049 (5) | 0.2159 (8) | 0.049* | |
O7 | 1.0306 (2) | −0.0718 (3) | 0.29892 (9) | 0.0307 (4) | |
H7A | 1.024 (3) | 0.017 (4) | 0.3286 (13) | 0.046* | |
H7B | 0.9363 (17) | −0.107 (4) | 0.2905 (16) | 0.046* | |
C1 | 0.3562 (2) | 0.2400 (3) | 0.01927 (10) | 0.0166 (4) | |
C2 | 0.5254 (2) | 0.2373 (3) | 0.01671 (10) | 0.0165 (4) | |
C3 | 0.60165 (9) | 0.28856 (11) | −0.04338 (4) | 0.0191 (4) | |
H3 | 0.7147 | 0.2866 | −0.0446 | 0.023* | |
C4 | 0.51580 (9) | 0.34244 (11) | −0.10149 (4) | 0.0202 (4) | |
H4 | 0.5698 | 0.3798 | −0.1416 | 0.024* | |
C5 | 0.35162 (9) | 0.34113 (11) | −0.10031 (4) | 0.0199 (4) | |
H5 | 0.2928 | 0.3768 | −0.1401 | 0.024* | |
C6 | 0.27022 (9) | 0.28780 (11) | −0.04124 (4) | 0.0173 (4) | |
C7 | 0.09381 (9) | 0.27567 (11) | −0.04348 (4) | 0.0214 (4) | |
C8 | 0.62914 (9) | 0.18023 (11) | 0.07343 (4) | 0.0178 (4) | |
H8 | 0.7404 | 0.1774 | 0.0654 | 0.021* | |
C9 | 0.70227 (9) | 0.06991 (11) | 0.18359 (4) | 0.0181 (4) | |
H9A | 0.8115 | 0.1060 | 0.1840 | 0.022* | |
H9B | 0.7886 | 0.0065 | 0.1631 | 0.022* | |
C10 | 0.62358 (9) | −0.06344 (11) | 0.23515 (4) | 0.0166 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.01372 (14) | 0.02076 (15) | 0.01347 (14) | −0.00010 (8) | 0.00097 (9) | −0.00047 (8) |
N1 | 0.0156 (8) | 0.0178 (9) | 0.0172 (9) | 0.0001 (6) | 0.0002 (7) | 0.0015 (7) |
O1 | 0.0243 (8) | 0.0353 (10) | 0.0231 (8) | −0.0049 (7) | −0.0080 (6) | 0.0029 (7) |
O2 | 0.0173 (8) | 0.0503 (11) | 0.0221 (8) | −0.0012 (7) | −0.0011 (6) | 0.0050 (8) |
O3 | 0.0150 (7) | 0.0335 (9) | 0.0160 (7) | −0.0007 (6) | 0.0009 (6) | 0.0043 (6) |
O4 | 0.0160 (7) | 0.0244 (8) | 0.0178 (7) | −0.0003 (6) | 0.0018 (5) | 0.0028 (6) |
O5 | 0.0155 (7) | 0.0242 (8) | 0.0183 (7) | −0.0016 (6) | −0.0014 (5) | 0.0058 (6) |
O6 | 0.0295 (9) | 0.0483 (11) | 0.0203 (8) | −0.0212 (8) | 0.0036 (7) | −0.0062 (8) |
O7 | 0.0183 (8) | 0.0427 (10) | 0.0312 (10) | −0.0054 (7) | 0.0042 (7) | −0.0095 (8) |
C1 | 0.0187 (10) | 0.0152 (9) | 0.0159 (9) | −0.0004 (8) | 0.0003 (8) | −0.0012 (7) |
C2 | 0.0177 (10) | 0.0155 (9) | 0.0163 (10) | 0.0002 (8) | 0.0010 (8) | −0.0008 (7) |
C3 | 0.0184 (10) | 0.0174 (10) | 0.0217 (10) | −0.0005 (8) | 0.0032 (8) | −0.0022 (8) |
C4 | 0.0272 (11) | 0.0205 (10) | 0.0130 (9) | −0.0024 (9) | 0.0042 (8) | −0.0001 (8) |
C5 | 0.0263 (11) | 0.0180 (10) | 0.0154 (10) | 0.0009 (9) | −0.0021 (8) | −0.0015 (8) |
C6 | 0.0202 (10) | 0.0163 (10) | 0.0154 (9) | −0.0007 (8) | −0.0015 (8) | −0.0028 (8) |
C7 | 0.0222 (11) | 0.0210 (11) | 0.0211 (10) | −0.0016 (8) | −0.0035 (8) | −0.0006 (8) |
C8 | 0.0160 (10) | 0.0176 (10) | 0.0197 (10) | −0.0005 (8) | 0.0012 (8) | −0.0005 (8) |
C9 | 0.0124 (9) | 0.0247 (10) | 0.0172 (10) | −0.0003 (8) | 0.0002 (7) | 0.0038 (8) |
C10 | 0.0200 (10) | 0.0172 (10) | 0.0126 (9) | −0.0018 (8) | −0.0002 (7) | −0.0022 (7) |
Zn1—O5i | 1.9951 (15) | O7—H7B | 0.85 (3) |
Zn1—O6 | 2.0065 (16) | C1—C6 | 1.4205 |
Zn1—N1 | 2.0161 (18) | C1—C2 | 1.423 (3) |
Zn1—O3 | 2.0234 (15) | C2—C3 | 1.395 (2) |
Zn1—O4 | 2.1211 (15) | C2—C8 | 1.4585 |
N1—C8 | 1.2866 | C3—C4 | 1.3916 |
N1—C9 | 1.4616 | C3—H3 | 0.9500 |
O1—C7 | 1.2300 | C4—C5 | 1.3794 |
O2—C7 | 1.3149 | C4—H4 | 0.9500 |
O2—H2 | 0.97 (3) | C5—C6 | 1.4031 |
O3—C1 | 1.317 (2) | C5—H5 | 0.9500 |
O4—C10 | 1.2426 | C6—C7 | 1.4840 |
O5—C10 | 1.2749 | C8—H8 | 0.9500 |
O5—Zn1ii | 1.9951 (15) | C9—C10 | 1.5233 |
O6—H6A | 0.837 (10) | C9—H9A | 0.9500 |
O6—H6B | 0.843 (10) | C9—H9B | 0.9415 |
O7—H7A | 0.85 (3) | ||
O5i—Zn1—O6 | 95.42 (7) | C4—C3—C2 | 121.46 |
O5i—Zn1—N1 | 118.12 (7) | C4—C3—H3 | 119.3 |
O6—Zn1—N1 | 145.80 (7) | C2—C3—H3 | 119.3 |
O5i—Zn1—O3 | 103.74 (6) | C5—C4—C3 | 119.4 |
O6—Zn1—O3 | 88.92 (7) | C5—C4—H4 | 120.3 |
N1—Zn1—O3 | 89.32 (7) | C3—C4—H4 | 120.3 |
O5i—Zn1—O4 | 100.26 (6) | C4—C5—C6 | 120.9 |
O6—Zn1—O4 | 88.14 (7) | C4—C5—H5 | 119.5 |
N1—Zn1—O4 | 79.92 (6) | C6—C5—H5 | 119.5 |
O3—Zn1—O4 | 155.98 (6) | C5—C6—C1 | 120.27 |
C8—N1—C9 | 118.66 | C5—C6—C7 | 119.2 |
C8—N1—Zn1 | 128.06 | C1—C6—C7 | 120.51 |
C9—N1—Zn1 | 113.16 | O1—C7—O2 | 120.32 |
C7—O2—H2 | 105.00 | O1—C7—C6 | 122.64 |
C1—O3—Zn1 | 129.71 (13) | O2—C7—C6 | 117.03 |
C10—O4—Zn1 | 113.89 | N1—C8—C2 | 125.64 |
C10—O5—Zn1ii | 123.30 (10) | N1—C8—H8 | 117.2 |
Zn1—O6—H6A | 133 (2) | C2—C8—H8 | 117.2 |
Zn1—O6—H6B | 119 (2) | N1—C9—C10 | 109.14 |
H6A—O6—H6B | 107.1 (16) | N1—C9—H9A | 125.4 |
H7A—O7—H7B | 105.9 (15) | C10—C9—H9A | 125.4 |
O3—C1—C6 | 119.00 | N1—C9—H9B | 112.0 |
O3—C1—C2 | 122.95 (18) | C10—C9—H9B | 110.5 |
C6—C1—C2 | 118.04 | H9A—C9—H9B | 51.3 |
C3—C2—C1 | 119.79 (16) | O4—C10—O5 | 124.37 |
C3—C2—C8 | 115.94 | O4—C10—C9 | 119.46 |
C1—C2—C8 | 124.27 | O5—C10—C9 | 116.16 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6A···O1iii | 0.84 (1) | 1.94 (3) | 2.768 (2) | 172 (3) |
O6—H6B···O7iv | 0.84 (1) | 1.80 (1) | 2.637 (2) | 173 (4) |
O7—H7A···O1v | 0.85 (3) | 1.96 (3) | 2.806 (2) | 175 (3) |
O7—H7B···O5 | 0.85 (3) | 1.92 (1) | 2.763 (2) | 176 (3) |
O2—H2···O3 | 0.97 (3) | 1.52 (3) | 2.450 (2) | 158 (3) |
Symmetry codes: (iii) −x, −y, −z; (iv) x−1, y, z; (v) x+1, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Zn(C10H7NO5)(H2O)]·H2O |
Mr | 322.59 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 173 |
a, b, c (Å) | 8.3985 (9), 6.8730 (7), 19.637 (2) |
β (°) | 90.781 (2) |
V (Å3) | 1133.4 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.20 |
Crystal size (mm) | 0.49 × 0.41 × 0.22 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.354, 0.617 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5599, 2479, 2171 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.026, 0.078, 1.06 |
No. of reflections | 2479 |
No. of parameters | 166 |
No. of restraints | 6 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.84, −0.87 |
Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1997), SHELXTL.
Zn1—O5i | 1.9951 (15) | Zn1—O3 | 2.0234 (15) |
Zn1—O6 | 2.0065 (16) | Zn1—O4 | 2.1211 (15) |
Zn1—N1 | 2.0161 (18) |
Symmetry code: (i) −x+1, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6A···O1ii | 0.837 (10) | 1.94 (3) | 2.768 (2) | 172 (3) |
O6—H6B···O7iii | 0.843 (10) | 1.798 (11) | 2.637 (2) | 173 (4) |
O7—H7A···O1iv | 0.85 (3) | 1.96 (3) | 2.806 (2) | 175 (3) |
O7—H7B···O5 | 0.85 (3) | 1.923 (10) | 2.763 (2) | 176 (3) |
O2—H2···O3 | 0.97 (3) | 1.52 (3) | 2.450 (2) | 158 (3) |
Symmetry codes: (ii) −x, −y, −z; (iii) x−1, y, z; (iv) x+1, −y+1/2, z+1/2. |
Schiff bases have been intensively investigated recently owing to their strong coordination capability and diverse biological activities, such as antibacterial, antitumor activities etc (Yang et al., 2000; May et al., 2004). Among these Schiff bases, aminophenol-containing Schiff base have received extraordinatry attention for its' flexible coordination codes. some unusual structures have been synthesized through these ligands, such as helical structures (Ranford et al.,1999;Erxleben,2001).
However, in those reported literatures, Seldom helical structures with the ligand of 3-Carboxysalicylaldehyde have been generated. We have reported two structures derived from the ligand 3-Carboxysalicylideneglycinate(Cai et al.,2006; Cai et al.,2007). As an extension of the work, We report here the preparations and crystal structure characterizations of the title helical coordination polymer(I).
The crystal structure of the title complex(I) is very similar to the former reported structure (Cai et al.,2007).there is one ZnIIatom,one 3-Carboxysalicylideneglycinate anion, one coordinated water molecule and one lattice water molecule in each independent crystallographic unit, Each ZnII atom adapts a square-based pyramidal geometry.It is worthy of mention that the remaining protonated carboxylate group does not participate in coordination, but involve in hydrogen bonding.In the title complex,each pair of adjacent ZnII atom are bridged by a carboxy group of the ligand to form a chiral helical chain running along a crystallographic 21 axis in the b direction with a pitch of 6.873 Å. There are two kinds of hydrogen bonding interactions in the title complex.The acidic H atom forms a strong intramolecular O—H···O hydrogen bond to the phenoxy O atom [O···O = 2.450 (2) Å]. The other hydrogen bonding interactions are involving the carboxylate O atoms and coordinated/uncoordinated water molecules. By which the chains are connected to form a three-dimensional network.