Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705163X/hb2593sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680705163X/hb2593Isup2.hkl |
CCDC reference: 632690
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.061
- wR factor = 0.194
- Data-to-parameter ratio = 11.4
checkCIF/PLATON results
No syntax errors found
Alert level B DIFMX01_ALERT_2_B The maximum difference density is > 0.1*ZMAX*1.00 _refine_diff_density_max given = 1.065 Test value = 0.800 PLAT094_ALERT_2_B Ratio of Maximum / Minimum Residual Density .... 4.65 PLAT097_ALERT_2_B Maximum (Positive) Residual Density ............ 1.07 e/A
Alert level C DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.38 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 5
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
4,4'-Azo-diphthalic acid (0.035 g, 0.16 mmol), NaOH (0.048 g, 0.12 mmol) and ZnSO4 (0.0028 g, 0.014 mmol) were added to a mixed solvent of ethanol and acetonitrile. The mixture was heated for five hours under reflux with stirring. The resulting liquid was then filtered to give a solution which was infiltrated by diethyl ether in a closed vessel. After a week, colourless blocks of (I) were recovered.
The C-bound and carboxylic acid H atoms were placed in calculated positions [C—H = 0.93 Å, O—H = 0.89 Å] and refined using a riding model, with Uiso(H) = 1.2Ueq(carrier). The water H atoms were found in a dffierent map and refined with O—H = 0.84 (2) Å and Uiso(H) = 1.5Ueq(O). The maximum difference peak is located on the N=N bond, 1.07 Å from N1.
In an attempt to prepare a Zn-containing coordination polymer (Carlucci et al., 2000), the title compound, (I), arose as an unexpected product.
The complete organic molecule (Fig. 1) is generated by inversion at the mid-point of the central N=N bond and a water molecule of crystallization completes the structure. The components interact by way of O—H···O hydrogen bonds to generate a two-dimesnional supramolecular architecture (Table 2).
For background, see: Carlucci et al. (2000).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2004); software used to prepare material for publication: SHELXTL (Bruker, 2004).
Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids (arbitaray spheres for the H atoms). Symmetry code: (i) 1 - x, 1 - y, 1 - z. |
C16H10N2O8·2H2O | Z = 1 |
Mr = 394.29 | F(000) = 204 |
Triclinic, P1 | Dx = 1.521 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.484 (2) Å | Cell parameters from 1533 reflections |
b = 6.491 (3) Å | θ = 1.6–25.2° |
c = 12.820 (5) Å | µ = 0.13 mm−1 |
α = 86.779 (6)° | T = 298 K |
β = 82.921 (5)° | Block, colourless |
γ = 71.956 (6)° | 0.28 × 0.24 × 0.19 mm |
V = 430.5 (3) Å3 |
Bruker APEXII CCD diffractometer | 1533 independent reflections |
Radiation source: fine-focus sealed tube | 1378 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.012 |
Detector resolution: 0 pixels mm-1 | θmax = 25.2°, θmin = 1.6° |
ω scans | h = −6→6 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | k = −4→7 |
Tmin = 0.965, Tmax = 0.976 | l = −15→15 |
2278 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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.194 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + (0.1258P)2 + 0.1677P] where P = (Fo2 + 2Fc2)/3 |
1533 reflections | (Δ/σ)max < 0.001 |
135 parameters | Δρmax = 1.07 e Å−3 |
5 restraints | Δρmin = −0.23 e Å−3 |
C16H10N2O8·2H2O | γ = 71.956 (6)° |
Mr = 394.29 | V = 430.5 (3) Å3 |
Triclinic, P1 | Z = 1 |
a = 5.484 (2) Å | Mo Kα radiation |
b = 6.491 (3) Å | µ = 0.13 mm−1 |
c = 12.820 (5) Å | T = 298 K |
α = 86.779 (6)° | 0.28 × 0.24 × 0.19 mm |
β = 82.921 (5)° |
Bruker APEXII CCD diffractometer | 1533 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | 1378 reflections with I > 2σ(I) |
Tmin = 0.965, Tmax = 0.976 | Rint = 0.012 |
2278 measured reflections |
R[F2 > 2σ(F2)] = 0.061 | 5 restraints |
wR(F2) = 0.194 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | Δρmax = 1.07 e Å−3 |
1533 reflections | Δρmin = −0.23 e Å−3 |
135 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 | ||
O2 | 0.2911 (4) | −0.1176 (3) | 0.13083 (13) | 0.0536 (6) | |
O1W | 0.8546 (4) | 0.6214 (3) | 0.15345 (14) | 0.0490 (5) | |
O4 | 0.7036 (3) | 0.1458 (4) | 0.07814 (13) | 0.0557 (6) | |
H4A | 0.7194 | 0.1419 | 0.0138 | 0.084* | |
O1 | −0.0028 (4) | −0.1294 (3) | 0.26625 (14) | 0.0546 (6) | |
H1 | −0.0448 | −0.2031 | 0.2261 | 0.082* | |
O3 | 0.2965 (4) | 0.3246 (4) | 0.05734 (13) | 0.0579 (6) | |
C5 | 0.4209 (5) | 0.3623 (4) | 0.39868 (19) | 0.0476 (7) | |
C2 | 0.2568 (5) | 0.0939 (4) | 0.27905 (18) | 0.0426 (6) | |
N1 | 0.5149 (5) | 0.5055 (4) | 0.45109 (17) | 0.0566 (7) | |
C8 | 0.4608 (5) | 0.2336 (4) | 0.11278 (17) | 0.0391 (6) | |
C7 | 0.4044 (4) | 0.2211 (4) | 0.23069 (17) | 0.0390 (6) | |
C6 | 0.4860 (5) | 0.3540 (4) | 0.29044 (19) | 0.0450 (6) | |
H4 | 0.5847 | 0.4378 | 0.2578 | 0.054* | |
C1 | 0.1826 (5) | −0.0600 (4) | 0.21811 (18) | 0.0417 (6) | |
C4 | 0.2685 (7) | 0.2389 (5) | 0.4474 (2) | 0.0604 (8) | |
H3 | 0.2205 | 0.2464 | 0.5196 | 0.072* | |
C3 | 0.1906 (6) | 0.1070 (5) | 0.3879 (2) | 0.0577 (8) | |
H2 | 0.0911 | 0.0241 | 0.4208 | 0.069* | |
H1WA | 0.748 (5) | 0.683 (5) | 0.111 (2) | 0.087* | |
H1WB | 0.981 (5) | 0.525 (5) | 0.124 (2) | 0.087* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.0578 (11) | 0.0728 (13) | 0.0361 (10) | −0.0289 (10) | 0.0053 (8) | −0.0230 (9) |
O1W | 0.0522 (11) | 0.0558 (11) | 0.0423 (10) | −0.0195 (8) | −0.0075 (8) | −0.0064 (8) |
O4 | 0.0476 (11) | 0.0861 (14) | 0.0287 (9) | −0.0145 (9) | 0.0008 (8) | −0.0083 (9) |
O1 | 0.0639 (12) | 0.0696 (13) | 0.0405 (10) | −0.0368 (10) | 0.0040 (8) | −0.0129 (9) |
O3 | 0.0552 (11) | 0.0787 (14) | 0.0293 (9) | −0.0048 (10) | −0.0052 (8) | −0.0039 (9) |
C5 | 0.0587 (15) | 0.0555 (15) | 0.0333 (13) | −0.0220 (12) | −0.0058 (11) | −0.0109 (11) |
C2 | 0.0483 (13) | 0.0531 (14) | 0.0279 (12) | −0.0178 (11) | −0.0012 (10) | −0.0073 (10) |
N1 | 0.0789 (16) | 0.0662 (15) | 0.0329 (10) | −0.0319 (13) | −0.0078 (10) | −0.0109 (10) |
C8 | 0.0463 (13) | 0.0451 (12) | 0.0276 (11) | −0.0167 (10) | −0.0006 (9) | −0.0075 (9) |
C7 | 0.0422 (12) | 0.0474 (13) | 0.0266 (11) | −0.0117 (10) | −0.0031 (9) | −0.0063 (9) |
C6 | 0.0544 (14) | 0.0510 (14) | 0.0340 (13) | −0.0222 (11) | −0.0040 (10) | −0.0060 (10) |
C1 | 0.0438 (13) | 0.0501 (13) | 0.0322 (12) | −0.0154 (10) | −0.0028 (9) | −0.0068 (10) |
C4 | 0.087 (2) | 0.0779 (19) | 0.0247 (12) | −0.0397 (17) | 0.0024 (12) | −0.0093 (12) |
C3 | 0.0796 (19) | 0.0784 (19) | 0.0286 (13) | −0.0466 (16) | 0.0051 (12) | −0.0093 (12) |
O2—C1 | 1.221 (3) | C2—C7 | 1.398 (3) |
O1W—H1WA | 0.84 (3) | C2—C3 | 1.399 (3) |
O1W—H1WB | 0.84 (3) | C2—C1 | 1.481 (3) |
O4—C8 | 1.307 (3) | N1—N1i | 1.245 (4) |
O4—H4A | 0.8200 | C8—C7 | 1.508 (3) |
O1—C1 | 1.310 (3) | C7—C6 | 1.389 (3) |
O1—H1 | 0.8200 | C6—H4 | 0.9300 |
O3—C8 | 1.203 (3) | C4—C3 | 1.370 (4) |
C5—C6 | 1.389 (4) | C4—H3 | 0.9300 |
C5—C4 | 1.400 (4) | C3—H2 | 0.9300 |
C5—N1 | 1.426 (4) | ||
H1WA—O1W—H1WB | 111.0 (17) | C6—C7—C8 | 117.9 (2) |
C8—O4—H4A | 109.5 | C2—C7—C8 | 121.7 (2) |
C1—O1—H1 | 109.5 | C7—C6—C5 | 120.3 (2) |
C6—C5—C4 | 119.8 (2) | C7—C6—H4 | 119.8 |
C6—C5—N1 | 115.0 (2) | C5—C6—H4 | 119.8 |
C4—C5—N1 | 125.2 (2) | O2—C1—O1 | 123.9 (2) |
C7—C2—C3 | 118.5 (2) | O2—C1—C2 | 121.5 (2) |
C7—C2—C1 | 121.2 (2) | O1—C1—C2 | 114.5 (2) |
C3—C2—C1 | 120.2 (2) | C3—C4—C5 | 119.5 (2) |
N1i—N1—C5 | 115.4 (3) | C3—C4—H3 | 120.3 |
O3—C8—O4 | 123.9 (2) | C5—C4—H3 | 120.3 |
O3—C8—C7 | 122.2 (2) | C4—C3—C2 | 121.7 (3) |
O4—C8—C7 | 113.8 (2) | C4—C3—H2 | 119.1 |
C6—C7—C2 | 120.2 (2) | C2—C3—H2 | 119.1 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1WB···O3ii | 0.84 (3) | 1.95 (3) | 2.782 (3) | 173 (4) |
O1W—H1WA···O2iii | 0.84 (3) | 2.43 (2) | 3.070 (3) | 134 (3) |
O1W—H1WA···O3iv | 0.84 (3) | 2.20 (2) | 2.895 (3) | 139 (3) |
O1—H1···O1Wv | 0.82 | 1.76 | 2.577 (2) | 173 |
O4—H4A···O2vi | 0.82 | 1.88 | 2.692 (2) | 171 |
Symmetry codes: (ii) x+1, y, z; (iii) x, y+1, z; (iv) −x+1, −y+1, −z; (v) x−1, y−1, z; (vi) −x+1, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C16H10N2O8·2H2O |
Mr | 394.29 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 5.484 (2), 6.491 (3), 12.820 (5) |
α, β, γ (°) | 86.779 (6), 82.921 (5), 71.956 (6) |
V (Å3) | 430.5 (3) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.13 |
Crystal size (mm) | 0.28 × 0.24 × 0.19 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2004) |
Tmin, Tmax | 0.965, 0.976 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2278, 1533, 1378 |
Rint | 0.012 |
(sin θ/λ)max (Å−1) | 0.599 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.194, 1.10 |
No. of reflections | 1533 |
No. of parameters | 135 |
No. of restraints | 5 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.07, −0.23 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2004).
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1WB···O3i | 0.84 (3) | 1.95 (3) | 2.782 (3) | 173 (4) |
O1W—H1WA···O2ii | 0.84 (3) | 2.43 (2) | 3.070 (3) | 134 (3) |
O1W—H1WA···O3iii | 0.84 (3) | 2.20 (2) | 2.895 (3) | 139 (3) |
O1—H1···O1Wiv | 0.82 | 1.76 | 2.577 (2) | 173.0 |
O4—H4A···O2v | 0.82 | 1.88 | 2.692 (2) | 170.8 |
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) −x+1, −y+1, −z; (iv) x−1, y−1, z; (v) −x+1, −y, −z. |
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In an attempt to prepare a Zn-containing coordination polymer (Carlucci et al., 2000), the title compound, (I), arose as an unexpected product.
The complete organic molecule (Fig. 1) is generated by inversion at the mid-point of the central N=N bond and a water molecule of crystallization completes the structure. The components interact by way of O—H···O hydrogen bonds to generate a two-dimesnional supramolecular architecture (Table 2).