Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800018420/na6013sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536800018420/na6013Isup2.hkl |
CCDC reference: 155861
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.039
- wR factor = 0.108
- Data-to-parameter ratio = 11.4
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
PLAT_353 Alert C Long N-H Bond (0.87A) N(2) - H(2C) = 1.04 Ang.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
The title compound was prepared by heating 13.5 mmol of phthalic anhydride in 30 ml of pyridine to 363 K and then adding 65 mmol of ethylenediamine dissolved in 10 ml of pyridine. Deposition of a white solid occurred immediately and the resulting mixture was refluxed for 24 h. The white solid was then filtered off and washed with acetone and dichloromethane. Hydrolysis of the material thus obtained in wet dimethyl sulfoxide and subsequent crystallization yielded rectangular crystals. Analysis calculated for C10H14N2O4: C 55.0, H 5.1, N 7.1%; found: C 55.0, H 5.0, N 7.1%.
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
C2H10N2+·C8H4O4− | Dx = 1.382 Mg m−3 |
Mr = 226.23 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 23 reflections |
a = 21.825 (3) Å | θ = 11.7–16.0° |
b = 12.384 (1) Å | µ = 0.11 mm−1 |
c = 8.048 (1) Å | T = 293 K |
V = 2175.2 (5) Å3 | Plate, colourless |
Z = 8 | 0.40 × 0.30 × 0.13 mm |
F(000) = 960 |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 25.1°, θmin = 1.9° |
Graphite monochromator | h = 0→26 |
θ/2θ scans | k = 0→14 |
1934 measured reflections | l = 0→9 |
1934 independent reflections | 2 standard reflections every 120 min |
1187 reflections with I > 2σ(I) | intensity decay: <1% |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0551P)2 + 0.137P] where P = (Fo2 + 2Fc2)/3 |
1934 reflections | (Δ/σ)max = 0.005 |
169 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C2H10N2+·C8H4O4− | V = 2175.2 (5) Å3 |
Mr = 226.23 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 21.825 (3) Å | µ = 0.11 mm−1 |
b = 12.384 (1) Å | T = 293 K |
c = 8.048 (1) Å | 0.40 × 0.30 × 0.13 mm |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.000 |
1934 measured reflections | 2 standard reflections every 120 min |
1934 independent reflections | intensity decay: <1% |
1187 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.108 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.16 e Å−3 |
1934 reflections | Δρmin = −0.23 e Å−3 |
169 parameters |
Experimental. General procedures for crystal alignment, unit cell determination and refinement and collection of intensity data have been published (Mague, J. T. & Lloyd, C. L. (1988). Organometallics 7, 983–993). |
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. H-atoms attached to nitrogen were refined with isotropic displacement parameters while the remainder of the H-atoms were placed in calculated positions riding on the attached carbon atoms. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.45383 (8) | 0.25649 (13) | 0.8137 (2) | 0.0501 (5) | |
O2 | 0.45026 (6) | 0.09791 (11) | 0.68450 (18) | 0.0321 (4) | |
O3 | 0.43446 (7) | −0.08491 (11) | 0.92898 (18) | 0.0304 (4) | |
O4 | 0.37479 (7) | −0.11955 (12) | 0.71160 (19) | 0.0356 (4) | |
C1 | 0.37142 (10) | 0.13762 (17) | 0.8774 (3) | 0.0306 (5) | |
C2 | 0.35097 (9) | 0.03069 (17) | 0.8853 (2) | 0.0255 (5) | |
C3 | 0.29507 (10) | 0.0086 (2) | 0.9601 (3) | 0.0388 (6) | |
H3 | 0.2806 | −0.0620 | 0.9618 | 0.047* | |
C4 | 0.26054 (12) | 0.0896 (2) | 1.0321 (3) | 0.0516 (7) | |
H4 | 0.2232 | 0.0736 | 1.0819 | 0.062* | |
C5 | 0.28193 (13) | 0.1941 (2) | 1.0296 (4) | 0.0569 (8) | |
H5 | 0.2594 | 0.2487 | 1.0801 | 0.068* | |
C6 | 0.33676 (12) | 0.21822 (19) | 0.9524 (3) | 0.0475 (7) | |
H6 | 0.3507 | 0.2892 | 0.9507 | 0.057* | |
C7 | 0.42957 (10) | 0.16706 (16) | 0.7859 (3) | 0.0304 (5) | |
C8 | 0.39011 (9) | −0.06396 (16) | 0.8334 (3) | 0.0245 (5) | |
N1 | 0.44854 (9) | 0.02739 (16) | 0.2289 (3) | 0.0311 (4) | |
H1A | 0.4425 (13) | 0.004 (2) | 0.114 (4) | 0.070 (9)* | |
H1B | 0.4870 (13) | −0.002 (2) | 0.258 (3) | 0.055 (8)* | |
H1C | 0.4496 (12) | 0.102 (2) | 0.239 (4) | 0.061 (8)* | |
N2 | 0.44276 (9) | −0.18674 (15) | 0.4390 (3) | 0.0299 (4) | |
H2A | 0.4305 (11) | −0.1677 (18) | 0.548 (3) | 0.038 (6)* | |
H2B | 0.4423 (11) | −0.259 (2) | 0.429 (3) | 0.043 (7)* | |
H2C | 0.4865 (12) | −0.159 (2) | 0.408 (3) | 0.054 (7)* | |
C9 | 0.39597 (10) | −0.13791 (17) | 0.3292 (3) | 0.0318 (5) | |
H9A | 0.3557 | −0.1620 | 0.3640 | 0.038* | |
H9B | 0.4025 | −0.1628 | 0.2163 | 0.038* | |
C10 | 0.39780 (10) | −0.01580 (17) | 0.3321 (3) | 0.0314 (5) | |
H10A | 0.3591 | 0.0123 | 0.2912 | 0.038* | |
H10B | 0.4029 | 0.0087 | 0.4458 | 0.038* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0644 (12) | 0.0261 (8) | 0.0599 (12) | −0.0115 (8) | 0.0042 (9) | −0.0016 (9) |
O2 | 0.0313 (8) | 0.0294 (8) | 0.0358 (9) | −0.0006 (6) | 0.0051 (7) | 0.0027 (7) |
O3 | 0.0363 (8) | 0.0263 (8) | 0.0287 (9) | 0.0046 (7) | −0.0045 (7) | 0.0018 (7) |
O4 | 0.0406 (9) | 0.0350 (9) | 0.0314 (9) | 0.0009 (7) | −0.0035 (8) | −0.0099 (7) |
C1 | 0.0351 (12) | 0.0271 (11) | 0.0294 (13) | 0.0066 (10) | 0.0006 (10) | 0.0003 (9) |
C2 | 0.0244 (10) | 0.0312 (11) | 0.0209 (11) | 0.0016 (9) | −0.0011 (9) | 0.0005 (9) |
C3 | 0.0302 (12) | 0.0474 (14) | 0.0387 (14) | 0.0012 (11) | 0.0051 (11) | 0.0052 (12) |
C4 | 0.0368 (14) | 0.074 (2) | 0.0440 (16) | 0.0169 (14) | 0.0134 (12) | 0.0049 (15) |
C5 | 0.0570 (17) | 0.0570 (18) | 0.0569 (18) | 0.0298 (15) | 0.0141 (15) | −0.0056 (15) |
C6 | 0.0578 (16) | 0.0353 (13) | 0.0494 (16) | 0.0157 (12) | 0.0082 (13) | −0.0025 (12) |
C7 | 0.0367 (12) | 0.0221 (10) | 0.0324 (13) | 0.0011 (10) | −0.0020 (10) | 0.0060 (10) |
C8 | 0.0276 (11) | 0.0228 (10) | 0.0231 (11) | −0.0036 (9) | 0.0043 (10) | 0.0034 (9) |
N1 | 0.0362 (11) | 0.0229 (9) | 0.0341 (11) | 0.0013 (8) | −0.0008 (10) | 0.0006 (9) |
N2 | 0.0364 (11) | 0.0230 (10) | 0.0304 (11) | −0.0007 (9) | 0.0058 (9) | 0.0001 (9) |
C9 | 0.0375 (12) | 0.0303 (12) | 0.0275 (13) | −0.0046 (10) | −0.0009 (10) | −0.0036 (10) |
C10 | 0.0345 (12) | 0.0309 (12) | 0.0289 (13) | 0.0048 (9) | 0.0003 (10) | −0.0021 (10) |
O1—C7 | 1.248 (3) | C2—C8 | 1.509 (3) |
O2—C7 | 1.266 (3) | C3—C4 | 1.381 (3) |
O3—C8 | 1.263 (2) | C4—C5 | 1.376 (4) |
O4—C8 | 1.244 (2) | C5—C6 | 1.381 (4) |
C1—C6 | 1.391 (3) | N1—C10 | 1.484 (3) |
C1—C2 | 1.399 (3) | N2—C9 | 1.480 (3) |
C1—C7 | 1.512 (3) | C9—C10 | 1.513 (3) |
C2—C3 | 1.388 (3) | ||
C6—C1—C2 | 119.1 (2) | C5—C6—C1 | 120.7 (2) |
C6—C1—C7 | 119.7 (2) | O1—C7—O2 | 124.4 (2) |
C2—C1—C7 | 121.22 (18) | O1—C7—C1 | 118.9 (2) |
C3—C2—C1 | 119.1 (2) | O2—C7—C1 | 116.75 (18) |
C3—C2—C8 | 117.70 (19) | O4—C8—O3 | 124.91 (19) |
C1—C2—C8 | 122.82 (18) | O4—C8—C2 | 119.72 (19) |
C4—C3—C2 | 121.3 (2) | O3—C8—C2 | 115.13 (18) |
C5—C4—C3 | 119.4 (2) | N2—C9—C10 | 112.40 (19) |
C4—C5—C6 | 120.3 (2) | N1—C10—C9 | 111.80 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O3i | 0.98 (3) | 1.85 (3) | 2.802 (3) | 161 (2) |
N1—H1B···O2ii | 0.95 (3) | 1.87 (3) | 2.788 (2) | 163 (2) |
N1—H1C···O1iii | 0.93 (3) | 1.85 (3) | 2.765 (3) | 166 (3) |
N2—H2A···O4 | 0.95 (2) | 1.89 (3) | 2.776 (3) | 155 (2) |
N2—H2B···O3iv | 0.90 (3) | 1.94 (3) | 2.835 (2) | 173 (2) |
N2—H2C···O2ii | 1.04 (3) | 1.74 (3) | 2.766 (2) | 166 (2) |
Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y, −z+1; (iii) x, −y+1/2, z−1/2; (iv) x, −y−1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C2H10N2+·C8H4O4− |
Mr | 226.23 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 293 |
a, b, c (Å) | 21.825 (3), 12.384 (1), 8.048 (1) |
V (Å3) | 2175.2 (5) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.40 × 0.30 × 0.13 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1934, 1934, 1187 |
Rint | 0.000 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.108, 1.01 |
No. of reflections | 1934 |
No. of parameters | 169 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.16, −0.23 |
Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, XCAD4 (Harms & Wocadlo, 1987), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O3i | 0.98 (3) | 1.85 (3) | 2.802 (3) | 161 (2) |
N1—H1B···O2ii | 0.95 (3) | 1.87 (3) | 2.788 (2) | 163 (2) |
N1—H1C···O1iii | 0.93 (3) | 1.85 (3) | 2.765 (3) | 166 (3) |
N2—H2A···O4 | 0.95 (2) | 1.89 (3) | 2.776 (3) | 155 (2) |
N2—H2B···O3iv | 0.90 (3) | 1.94 (3) | 2.835 (2) | 173 (2) |
N2—H2C···O2ii | 1.04 (3) | 1.74 (3) | 2.766 (2) | 166 (2) |
Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y, −z+1; (iii) x, −y+1/2, z−1/2; (iv) x, −y−1/2, z−1/2. |
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The phthalate salt [NH3(CH2)2NH3][1,2-C6H4(COO)2], (I), was obtained in the course of studies of the hydrolytic processes of phthalimides to phthalates through phthalamate intermediates which are of interest as efficient sensitizers for EuIII and TbIII photoluminescence (Barrett et al., 1995, 1998). The structure consists of sheets of cations sandwiched between two sheets of anions. There is extensive hydrogen bonding between the cations and anions.