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The title adduct
N-(2-ammonioethyl)-2-hydroxybenzamide picrate, C
9H
13N
2O
2+·C
6H
2N
3O
7−, contains an asymmetric N—H
O hydrogen bonds involving one N and three O atoms. The unit-cell packing is influenced by a network of intermolecular hydrogen bonds and π–π stacking of the aromatic rings.
Supporting information
CCDC reference: 192748
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- R factor = 0.052
- wR factor = 0.142
- Data-to-parameter ratio = 11.9
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
PLAT_737 Alert C D...A Calc 3.035(4), Rep 3.0350(10) .... 4.00 su-Ratio
N2 -O9 1.555 2.656
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Salicylate (1.5 g, 10 mmol) was dissolved in neat ethylenediamine (3.0 g, 50 mmol) and refluxed for 4 h. The solution was concentrated under vacuum yielding a light-brown oil. The oil was dissolved in 20 ml e thanol and added dropwise to a same solution (20 ml) of 2,4,6-trinitrophenol (2.3 g, 10 mmol). The resulting solution was refluxed for 1 h and concentrated to 20 ml. The mixture was filtered hot. The filtrate was then kept at room temperature and yellow crystals were obtained. Analysis calculated for C15H15N5O9: C 44.01, H 3.70, N 17.11; found: C 43.70, H 3.88, N 17.00%.
Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
N-(2-aminoethyl)-2-hydroxybenzamide picrate
top
Crystal data top
C15H15N5O9 | F(000) = 848 |
Mr = 409.32 | Dx = 1.518 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 12.761 (3) Å | Cell parameters from 27 reflections |
b = 8.005 (2) Å | θ = 3.0–13.2° |
c = 17.744 (6) Å | µ = 0.13 mm−1 |
β = 98.84 (3)° | T = 295 K |
V = 1790.9 (8) Å3 | Monoclinic, yellow |
Z = 4 | 0.56 × 0.44 × 0.40 mm |
Data collection top
Siemens P4 diffractometer | Rint = 0.020 |
Radiation source: normal-focus sealed tube | θmax = 25.0°, θmin = 1.8° |
Graphite monochromator | h = 0→15 |
ω scans | k = 0→9 |
3305 measured reflections | l = −21→20 |
3154 independent reflections | 3 standard reflections every 97 reflections |
1801 reflections with I > 2σ(I) | intensity decay: 2.8% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.142 | w = 1/[σ2(Fo2) + (0.074P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.94 | (Δ/σ)max < 0.001 |
3154 reflections | Δρmax = 0.31 e Å−3 |
265 parameters | Δρmin = −0.23 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0056 (13) |
Crystal data top
C15H15N5O9 | V = 1790.9 (8) Å3 |
Mr = 409.32 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.761 (3) Å | µ = 0.13 mm−1 |
b = 8.005 (2) Å | T = 295 K |
c = 17.744 (6) Å | 0.56 × 0.44 × 0.40 mm |
β = 98.84 (3)° | |
Data collection top
Siemens P4 diffractometer | Rint = 0.020 |
3305 measured reflections | 3 standard reflections every 97 reflections |
3154 independent reflections | intensity decay: 2.8% |
1801 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 0.94 | Δρmax = 0.31 e Å−3 |
3154 reflections | Δρmin = −0.23 e Å−3 |
265 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.8080 (2) | −0.0748 (3) | 0.51533 (13) | 0.0763 (7) | |
H1 | 0.8005 | −0.0641 | 0.5602 | 0.092* | |
O2 | 0.71836 (17) | 0.0335 (3) | 0.62923 (11) | 0.0572 (6) | |
N1 | 0.5678 (2) | 0.1805 (3) | 0.60658 (13) | 0.0510 (7) | |
H1N | 0.5228 | 0.2311 | 0.5732 | 0.061* | |
N2 | 0.7215 (2) | 0.2678 (3) | 0.76478 (12) | 0.0522 (7) | |
H2A | 0.7193 | 0.1723 | 0.7902 | 0.063* | |
H2B | 0.7517 | 0.3465 | 0.7963 | 0.063* | |
H2C | 0.7591 | 0.2534 | 0.7270 | 0.063* | |
C1 | 0.7334 (3) | 0.0136 (4) | 0.47126 (17) | 0.0529 (8) | |
C2 | 0.7383 (3) | 0.0134 (4) | 0.39318 (19) | 0.0675 (10) | |
H2 | 0.7895 | −0.0501 | 0.3743 | 0.081* | |
C3 | 0.6682 (3) | 0.1062 (5) | 0.34464 (19) | 0.0707 (10) | |
H3 | 0.6725 | 0.1071 | 0.2928 | 0.085* | |
C4 | 0.5914 (3) | 0.1980 (5) | 0.37166 (18) | 0.0689 (10) | |
H4 | 0.5445 | 0.2622 | 0.3382 | 0.083* | |
C5 | 0.5833 (3) | 0.1959 (4) | 0.44750 (16) | 0.0560 (8) | |
H5 | 0.5300 | 0.2571 | 0.4650 | 0.067* | |
C6 | 0.6546 (2) | 0.1026 (3) | 0.49972 (14) | 0.0419 (7) | |
C7 | 0.6480 (2) | 0.1033 (3) | 0.58249 (15) | 0.0416 (7) | |
C8 | 0.5506 (2) | 0.1855 (4) | 0.68561 (16) | 0.0563 (8) | |
H8A | 0.5698 | 0.0779 | 0.7089 | 0.068* | |
H8B | 0.4756 | 0.2025 | 0.6867 | 0.068* | |
C9 | 0.6122 (3) | 0.3197 (4) | 0.73289 (17) | 0.0582 (9) | |
H9A | 0.6155 | 0.4182 | 0.7015 | 0.070* | |
H9B | 0.5746 | 0.3499 | 0.7745 | 0.070* | |
O3 | 0.69062 (17) | −0.0284 (2) | 0.84008 (10) | 0.0532 (6) | |
O4 | 0.8397 (2) | 0.1505 (4) | 0.92114 (14) | 0.0921 (9) | |
O5 | 0.8655 (2) | 0.1248 (3) | 1.04270 (14) | 0.0809 (8) | |
O6 | 0.6136 (3) | −0.1328 (4) | 1.17567 (14) | 0.1018 (10) | |
O7 | 0.4992 (3) | −0.2975 (5) | 1.11658 (15) | 0.1290 (14) | |
O8 | 0.4262 (2) | −0.2668 (4) | 0.83869 (14) | 0.0969 (10) | |
O9 | 0.5702 (2) | −0.2983 (3) | 0.79256 (13) | 0.0733 (7) | |
N3 | 0.8138 (2) | 0.0951 (3) | 0.98020 (16) | 0.0571 (7) | |
N4 | 0.5694 (3) | −0.1959 (4) | 1.11798 (17) | 0.0727 (9) | |
N5 | 0.5229 (2) | −0.2530 (3) | 0.84301 (14) | 0.0557 (7) | |
C10 | 0.6675 (2) | −0.0667 (3) | 0.90373 (14) | 0.0397 (7) | |
C11 | 0.7197 (2) | −0.0069 (3) | 0.97670 (15) | 0.0415 (7) | |
C12 | 0.6879 (2) | −0.0472 (4) | 1.04454 (15) | 0.0482 (8) | |
H12 | 0.7242 | −0.0044 | 1.0899 | 0.058* | |
C13 | 0.6025 (2) | −0.1510 (4) | 1.04568 (15) | 0.0484 (8) | |
C14 | 0.5481 (2) | −0.2175 (4) | 0.97948 (16) | 0.0497 (8) | |
H14 | 0.4905 | −0.2881 | 0.9807 | 0.060* | |
C15 | 0.5807 (2) | −0.1771 (3) | 0.91208 (14) | 0.0423 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0764 (17) | 0.0796 (18) | 0.0709 (15) | 0.0281 (14) | 0.0048 (14) | 0.0033 (14) |
O2 | 0.0648 (15) | 0.0568 (13) | 0.0450 (11) | 0.0143 (12) | −0.0073 (10) | 0.0069 (10) |
N1 | 0.0544 (16) | 0.0581 (16) | 0.0391 (13) | 0.0065 (14) | 0.0029 (11) | 0.0021 (12) |
N2 | 0.079 (2) | 0.0457 (15) | 0.0312 (12) | −0.0167 (14) | 0.0073 (12) | −0.0031 (10) |
C1 | 0.054 (2) | 0.0481 (18) | 0.0539 (19) | 0.0038 (17) | −0.0016 (15) | −0.0049 (15) |
C2 | 0.068 (2) | 0.075 (2) | 0.063 (2) | 0.004 (2) | 0.0197 (18) | −0.0168 (19) |
C3 | 0.087 (3) | 0.081 (3) | 0.0410 (18) | −0.010 (2) | 0.0013 (19) | −0.0100 (18) |
C4 | 0.074 (2) | 0.081 (2) | 0.0451 (19) | 0.006 (2) | −0.0094 (17) | 0.0027 (18) |
C5 | 0.061 (2) | 0.060 (2) | 0.0424 (17) | 0.0008 (17) | −0.0066 (15) | 0.0011 (15) |
C6 | 0.0446 (17) | 0.0392 (16) | 0.0393 (15) | −0.0018 (14) | −0.0023 (13) | −0.0042 (13) |
C7 | 0.0497 (18) | 0.0322 (15) | 0.0397 (15) | −0.0032 (14) | −0.0033 (14) | −0.0001 (13) |
C8 | 0.0534 (19) | 0.067 (2) | 0.0513 (18) | −0.0085 (17) | 0.0162 (15) | −0.0011 (16) |
C9 | 0.084 (3) | 0.0462 (19) | 0.0497 (18) | −0.0013 (18) | 0.0263 (17) | −0.0036 (15) |
O3 | 0.0784 (15) | 0.0446 (12) | 0.0402 (11) | −0.0090 (11) | 0.0204 (10) | 0.0006 (9) |
O4 | 0.0848 (19) | 0.126 (2) | 0.0659 (16) | −0.0506 (17) | 0.0144 (14) | 0.0073 (16) |
O5 | 0.0853 (18) | 0.0812 (18) | 0.0679 (16) | −0.0286 (15) | −0.0145 (14) | 0.0001 (13) |
O6 | 0.153 (3) | 0.117 (2) | 0.0392 (14) | −0.017 (2) | 0.0273 (16) | −0.0098 (15) |
O7 | 0.121 (3) | 0.206 (4) | 0.0659 (18) | −0.069 (3) | 0.0318 (17) | 0.024 (2) |
O8 | 0.0717 (19) | 0.145 (3) | 0.0702 (16) | −0.0466 (18) | −0.0006 (14) | 0.0057 (16) |
O9 | 0.0835 (18) | 0.0843 (18) | 0.0493 (13) | −0.0027 (14) | 0.0018 (13) | −0.0190 (12) |
N3 | 0.0628 (18) | 0.0525 (16) | 0.0533 (16) | −0.0080 (14) | 0.0003 (14) | −0.0026 (14) |
N4 | 0.081 (2) | 0.093 (2) | 0.0482 (18) | −0.002 (2) | 0.0222 (16) | 0.0105 (17) |
N5 | 0.0615 (19) | 0.0600 (18) | 0.0429 (15) | −0.0146 (14) | −0.0011 (14) | 0.0102 (13) |
C10 | 0.0519 (18) | 0.0316 (15) | 0.0366 (15) | 0.0059 (14) | 0.0099 (13) | 0.0037 (12) |
C11 | 0.0484 (18) | 0.0342 (15) | 0.0427 (16) | −0.0015 (14) | 0.0096 (13) | −0.0022 (12) |
C12 | 0.058 (2) | 0.0491 (18) | 0.0365 (16) | 0.0096 (16) | 0.0026 (14) | −0.0046 (13) |
C13 | 0.0539 (19) | 0.060 (2) | 0.0341 (15) | 0.0080 (17) | 0.0137 (14) | 0.0057 (14) |
C14 | 0.0488 (18) | 0.0530 (19) | 0.0476 (17) | −0.0024 (15) | 0.0088 (14) | 0.0101 (14) |
C15 | 0.0477 (17) | 0.0410 (16) | 0.0365 (15) | 0.0003 (14) | 0.0015 (12) | 0.0052 (13) |
Geometric parameters (Å, º) top
O1—C1 | 1.337 (4) | C8—H8A | 0.9700 |
O1—H1 | 0.8200 | C8—H8B | 0.9700 |
O2—C7 | 1.256 (3) | C9—H9A | 0.9700 |
N1—C7 | 1.321 (4) | C9—H9B | 0.9700 |
N1—C8 | 1.453 (3) | O3—C10 | 1.249 (3) |
N1—H1N | 0.8600 | O4—N3 | 1.229 (3) |
N2—C9 | 1.482 (4) | O5—N3 | 1.223 (3) |
N2—H2A | 0.8900 | O6—N4 | 1.201 (4) |
N2—H2B | 0.8900 | O7—N4 | 1.207 (4) |
N2—H2C | 0.8900 | O8—N5 | 1.229 (3) |
C1—C6 | 1.390 (4) | O9—N5 | 1.209 (3) |
C1—C2 | 1.397 (4) | N3—C11 | 1.446 (4) |
C2—C3 | 1.363 (5) | N4—C13 | 1.456 (4) |
C2—H2 | 0.9300 | N5—C15 | 1.462 (4) |
C3—C4 | 1.370 (5) | C10—C15 | 1.442 (4) |
C3—H3 | 0.9300 | C10—C11 | 1.444 (4) |
C4—C5 | 1.365 (4) | C11—C12 | 1.366 (4) |
C4—H4 | 0.9300 | C12—C13 | 1.374 (4) |
C5—C6 | 1.409 (4) | C12—H12 | 0.9300 |
C5—H5 | 0.9300 | C13—C14 | 1.376 (4) |
C6—C7 | 1.484 (4) | C14—C15 | 1.364 (4) |
C8—C9 | 1.508 (4) | C14—H14 | 0.9300 |
| | | |
C1—O1—H1 | 109.5 | C9—C8—H8B | 108.7 |
C7—N1—C8 | 124.4 (3) | H8A—C8—H8B | 107.6 |
C7—N1—H1N | 117.8 | N2—C9—C8 | 113.1 (3) |
C8—N1—H1N | 117.8 | N2—C9—H9A | 109.0 |
C9—N2—H2A | 109.5 | C8—C9—H9A | 109.0 |
C9—N2—H2B | 109.5 | N2—C9—H9B | 109.0 |
H2A—N2—H2B | 109.5 | C8—C9—H9B | 109.0 |
C9—N2—H2C | 109.5 | H9A—C9—H9B | 107.8 |
H2A—N2—H2C | 109.5 | O5—N3—O4 | 121.7 (3) |
H2B—N2—H2C | 109.5 | O5—N3—C11 | 118.5 (3) |
O1—C1—C6 | 123.3 (3) | O4—N3—C11 | 119.8 (3) |
O1—C1—C2 | 116.3 (3) | O6—N4—O7 | 123.4 (3) |
C6—C1—C2 | 120.4 (3) | O6—N4—C13 | 119.0 (3) |
C3—C2—C1 | 120.1 (3) | O7—N4—C13 | 117.6 (3) |
C3—C2—H2 | 120.0 | O9—N5—O8 | 122.5 (3) |
C1—C2—H2 | 120.0 | O9—N5—C15 | 120.0 (3) |
C2—C3—C4 | 120.5 (3) | O8—N5—C15 | 117.5 (3) |
C2—C3—H3 | 119.8 | O3—C10—C15 | 122.4 (2) |
C4—C3—H3 | 119.8 | O3—C10—C11 | 126.1 (3) |
C5—C4—C3 | 120.3 (3) | C15—C10—C11 | 111.5 (2) |
C5—C4—H4 | 119.9 | C12—C11—C10 | 123.6 (3) |
C3—C4—H4 | 119.9 | C12—C11—N3 | 116.9 (3) |
C4—C5—C6 | 121.1 (3) | C10—C11—N3 | 119.4 (2) |
C4—C5—H5 | 119.4 | C11—C12—C13 | 120.0 (3) |
C6—C5—H5 | 119.4 | C11—C12—H12 | 120.0 |
C1—C6—C5 | 117.6 (3) | C13—C12—H12 | 120.0 |
C1—C6—C7 | 121.1 (3) | C12—C13—C14 | 121.2 (3) |
C5—C6—C7 | 121.3 (3) | C12—C13—N4 | 120.0 (3) |
O2—C7—N1 | 120.3 (3) | C14—C13—N4 | 118.7 (3) |
O2—C7—C6 | 120.6 (3) | C15—C14—C13 | 118.4 (3) |
N1—C7—C6 | 119.1 (3) | C15—C14—H14 | 120.8 |
N1—C8—C9 | 114.4 (2) | C13—C14—H14 | 120.8 |
N1—C8—H8A | 108.7 | C14—C15—C10 | 125.3 (3) |
C9—C8—H8A | 108.7 | C14—C15—N5 | 117.0 (3) |
N1—C8—H8B | 108.7 | C10—C15—N5 | 117.7 (2) |
| | | |
O1—C1—C2—C3 | −177.1 (3) | O4—N3—C11—C12 | −172.1 (3) |
C6—C1—C2—C3 | 2.6 (5) | O5—N3—C11—C10 | −169.8 (3) |
C1—C2—C3—C4 | −1.0 (6) | O4—N3—C11—C10 | 10.7 (4) |
C2—C3—C4—C5 | −0.9 (6) | C10—C11—C12—C13 | 0.5 (4) |
C3—C4—C5—C6 | 1.3 (5) | N3—C11—C12—C13 | −176.5 (3) |
O1—C1—C6—C5 | 177.5 (3) | C11—C12—C13—C14 | 0.6 (4) |
C2—C1—C6—C5 | −2.2 (4) | C11—C12—C13—N4 | 179.2 (3) |
O1—C1—C6—C7 | −0.5 (5) | O6—N4—C13—C12 | 4.6 (5) |
C2—C1—C6—C7 | 179.7 (3) | O7—N4—C13—C12 | −174.3 (3) |
C4—C5—C6—C1 | 0.3 (5) | O6—N4—C13—C14 | −176.8 (3) |
C4—C5—C6—C7 | 178.4 (3) | O7—N4—C13—C14 | 4.2 (5) |
C8—N1—C7—O2 | −3.0 (4) | C12—C13—C14—C15 | −0.3 (4) |
C8—N1—C7—C6 | 177.9 (3) | N4—C13—C14—C15 | −178.9 (3) |
C1—C6—C7—O2 | 5.3 (4) | C13—C14—C15—C10 | −1.2 (5) |
C5—C6—C7—O2 | −172.7 (3) | C13—C14—C15—N5 | 178.6 (3) |
C1—C6—C7—N1 | −175.6 (3) | O3—C10—C15—C14 | −176.6 (3) |
C5—C6—C7—N1 | 6.4 (4) | C11—C10—C15—C14 | 2.1 (4) |
C7—N1—C8—C9 | 83.6 (4) | O3—C10—C15—N5 | 3.6 (4) |
N1—C8—C9—N2 | −84.9 (3) | C11—C10—C15—N5 | −177.6 (2) |
O3—C10—C11—C12 | 176.9 (3) | O9—N5—C15—C14 | −141.6 (3) |
C15—C10—C11—C12 | −1.8 (4) | O8—N5—C15—C14 | 38.9 (4) |
O3—C10—C11—N3 | −6.1 (4) | O9—N5—C15—C10 | 38.1 (4) |
C15—C10—C11—N3 | 175.2 (2) | O8—N5—C15—C10 | −141.3 (3) |
O5—N3—C11—C12 | 7.4 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.82 | 1.90 | 2.618 (3) | 146 |
N2—H2B···O2i | 0.89 | 1.99 | 2.865 (3) | 165 |
N2—H2A···O3 | 0.89 | 1.90 | 2.779 (3) | 171 |
N1—H1N···O5ii | 0.86 | 2.31 | 3.078 (8) | 150 |
N2—H2A···O4 | 0.89 | 2.59 | 3.093 (2) | 117 |
N2—H2C···O2 | 0.89 | 2.47 | 3.045 (4) | 123 |
N2—H2C···O3i | 0.89 | 2.26 | 2.832 (4) | 122 |
N2—H2C···O9i | 0.89 | 2.30 | 3.035 (1) | 141 |
C2—H2···O8iii | 0.93 | 2.44 | 3.360 (6) | 174 |
C4—H4···O9iv | 0.93 | 2.56 | 3.397 (2) | 150 |
C5—H5···O4ii | 0.93 | 2.54 | 3.308 (6) | 140 |
C9—H9B···O7v | 0.97 | 2.31 | 3.217 (7) | 154 |
Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) x+1/2, −y−1/2, z−1/2; (iv) −x+1, −y, −z+1; (v) −x+1, −y, −z+2. |
Experimental details
Crystal data |
Chemical formula | C15H15N5O9 |
Mr | 409.32 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 295 |
a, b, c (Å) | 12.761 (3), 8.005 (2), 17.744 (6) |
β (°) | 98.84 (3) |
V (Å3) | 1790.9 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.13 |
Crystal size (mm) | 0.56 × 0.44 × 0.40 |
|
Data collection |
Diffractometer | Siemens P4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3305, 3154, 1801 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.595 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.142, 0.94 |
No. of reflections | 3154 |
No. of parameters | 265 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.23 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.82 | 1.90 | 2.618 (3) | 146 |
N2—H2B···O2i | 0.89 | 1.99 | 2.865 (3) | 165 |
N2—H2A···O3 | 0.89 | 1.90 | 2.779 (3) | 171 |
N1—H1N···O5ii | 0.86 | 2.31 | 3.078 (8) | 150 |
N2—H2A···O4 | 0.89 | 2.59 | 3.093 (2) | 117 |
N2—H2C···O2 | 0.89 | 2.47 | 3.045 (4) | 123 |
N2—H2C···O3i | 0.89 | 2.26 | 2.832 (4) | 122 |
N2—H2C···O9i | 0.89 | 2.30 | 3.035 (1) | 141 |
C2—H2···O8iii | 0.93 | 2.44 | 3.360 (6) | 174 |
C9—H9B···O7iv | 0.97 | 2.31 | 3.217 (7) | 154 |
Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) x+1/2, −y−1/2, z−1/2; (iv) −x+1, −y, −z+2. |
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Schiff bases are important ligands in coordination chemistry because they have applications in catalysis, medicine and magnetism, and they show biological activity (Vigato & Fenton, 1987; Yao et al., 2000). The amido group (HN—C═O) also has special biological activity and there are analogies between the amide and the Schiff bases. By combining a Schiff base and an amide in one reaction, Yao Ke-Min and co-workers suggested that the differences N properties could lead to some mixed or polymeric Schiff bases (Wu et al., 2001). Therefore, we selected N-(2-aminoethyl)-2-hydroxybenzamide for the synthesis of this type of amine. Because we could not find the KU-2 cation-exchange resin (Isagulyants et al., 1972), and the inconvenience of chromatography (Kutz et al., 1996), we made use of the amine salt formed by the amine–acid to purify the complex.
The crystal structure of the title compound, (I), showed it to be a 1:1 adduct. A plot of this adduct is shown in Fig. 1. The two aromatic rings are approximately perpendicular to one another (dihedral angle between corresponding mean planes is ca 75.9°). There are two intramolecular hydrogen bonds in the N-(2-aminioethyl)-2-hydroxybenzamide fragment, viz. O1—H1···O2 at 2.618 (3) Å and N2—H2C···O2 at 3.045 (40) Å. A difference map showed that the H atom in the hydrogen bond between phenoxy atom O3 and amino atom N2 was localized on the N atom, indicating that the N atom is positively charged and the O atom negatively charged. The connection between the acid and salicylamide moiety is completed by four additional N—H···O hydrogen bonds. Geometric parameters for the hydrogen bonds, including two C—H···O bonds, are presented in Table 1.
In the crystal, the benzene rings of N-(2-aminioethyl)-2-hydroxybenzamide are interlaced with the benzene rings of picric acid, to form columns along the a,b axis. This is illustrated in the packing diagram seen in Fig. 2. The interplanar distances between adjacent rings are about 2.96 and 3.36 Å, respectively. Each benzene ring is linked by N—H···O interactions to two adjacent nearly perpendicular aromatic ring columns related by a translation along c to give the appearance of a zigzag chain. The chains interact through N—H···O and C—H···O interactions to complete a three-dimensional network of adducts.