organic compounds
Ethyl 4-amino-3-methylbenzoate
aDepartment of Pharmaceutical Engineering, College of Life Sciences and Pharmaceutical Engineering, Nanjing University of Technolgy, Xinmofan Road No. 5, Nanjing 210009, People's Republic of China, and bBioengineering Department, Xuzhou Higher Vocational College of Bioengineering, Mine West Road, Xuzhou, Xuzhou 221006, People's Republic of China
*Correspondence e-mail: dcwang@njut.edu.cn
The 10H13NO2, contains two molecules which are linked via an N—H⋯N hydrogen bonds to form a dimer. These dimers are further linked via N—H⋯O intermolecular hydrogen bonds.
of the title compound, CRelated literature
For related literature, see: Baraldi et al. (1999, 2000, 2003, 2007); Wang et al. (2003); Zaffaroni et al. (2002). For bond-length data, see: Allen et al. (1987).
Experimental
Crystal data
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Refinement
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Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97
Supporting information
10.1107/S1600536808005989/er2050sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808005989/er2050Isup2.hkl
The title compound was prepared from 3-Methyl-4-aminobenzoic acid (15.2 g, 100 mmole) in ethanol (40.4 ml, 1000 mmole). After the solid has melted, concentrated hydrochloric acid (142 g, 120 ml) was added dropwise from a dropping funnel at 90°C, the the reaction mixture was cooled with ice and water and finaly the product was filtered by suction. Suitable crystals were obtained by evaporation of a methanol solution for about 3 d.
All H atoms were placed geometrically at the distances of 0.93–0.97 Å for C—H and 0.86 Å for N—H and included in the
in riding motion approximation with Uiso(H) = 1.2 or 1.5Ueq of the carrier atom.Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell
CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4(Harms & Wocadlo,1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. A view of the molecular structure of (I), showing displacement ellipsoids at the 50% probability level. N—H···N hydrogen bonds are shown as dashed lines. |
C10H13NO2 | Z = 4 |
Mr = 179.21 | F(000) = 384 |
Triclinic, P1 | Dx = 1.190 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.0110 (16) Å | Cell parameters from 25 reflections |
b = 8.7030 (17) Å | θ = 10–14° |
c = 15.835 (3) Å | µ = 0.08 mm−1 |
α = 90.78 (3)° | T = 298 K |
β = 95.13 (3)° | Block, colorless |
γ = 114.34 (3)° | 0.30 × 0.20 × 0.10 mm |
V = 1000.3 (3) Å3 |
Enraf–Nonius CAD-4 diffractometer | 2146 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.052 |
Graphite monochromator | θmax = 25.2°, θmin = 1.3° |
ω/2θ scans | h = −9→9 |
Absorption correction: ψ scan (North et al., 1968) | k = −10→10 |
Tmin = 0.975, Tmax = 0.991 | l = 0→18 |
3874 measured reflections | 3 standard reflections every 200 reflections |
3594 independent reflections | intensity decay: none |
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)] = 0.075 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.177 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.04P)2 + 1.2P] where P = (Fo2 + 2Fc2)/3 |
3594 reflections | (Δ/σ)max < 0.001 |
235 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C10H13NO2 | γ = 114.34 (3)° |
Mr = 179.21 | V = 1000.3 (3) Å3 |
Triclinic, P1 | Z = 4 |
a = 8.0110 (16) Å | Mo Kα radiation |
b = 8.7030 (17) Å | µ = 0.08 mm−1 |
c = 15.835 (3) Å | T = 298 K |
α = 90.78 (3)° | 0.30 × 0.20 × 0.10 mm |
β = 95.13 (3)° |
Enraf–Nonius CAD-4 diffractometer | 2146 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.052 |
Tmin = 0.975, Tmax = 0.991 | 3 standard reflections every 200 reflections |
3874 measured reflections | intensity decay: none |
3594 independent reflections |
R[F2 > 2σ(F2)] = 0.075 | 0 restraints |
wR(F2) = 0.177 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.23 e Å−3 |
3594 reflections | Δρmin = −0.23 e Å−3 |
235 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 | ||
O1 | 1.2476 (4) | 0.4839 (3) | 1.01662 (15) | 0.0684 (7) | |
O2 | 1.2577 (4) | 0.5912 (3) | 0.88836 (15) | 0.0742 (8) | |
N1 | 0.5942 (5) | −0.1423 (4) | 0.8227 (2) | 0.0872 (11) | |
H1A | 0.5484 | −0.2192 | 0.8580 | 0.105* | |
H1B | 0.5509 | −0.1604 | 0.7701 | 0.105* | |
C1 | 1.4390 (7) | 0.6205 (6) | 1.1432 (2) | 0.0884 (13) | |
H1C | 1.5389 | 0.7220 | 1.1674 | 0.133* | |
H1D | 1.4718 | 0.5267 | 1.1505 | 0.133* | |
H1E | 1.3311 | 0.6012 | 1.1712 | 0.133* | |
C2 | 1.3999 (6) | 0.6384 (5) | 1.0501 (2) | 0.0695 (10) | |
H2A | 1.3681 | 0.7338 | 1.0420 | 0.083* | |
H2B | 1.5077 | 0.6571 | 1.0211 | 0.083* | |
C3 | 1.1842 (5) | 0.4730 (4) | 0.9338 (2) | 0.0549 (8) | |
C4 | 1.0343 (5) | 0.3145 (4) | 0.9073 (2) | 0.0514 (8) | |
C5 | 0.9506 (5) | 0.1886 (4) | 0.9638 (2) | 0.0620 (10) | |
H5A | 0.9932 | 0.2072 | 1.0212 | 0.074* | |
C6 | 0.8093 (5) | 0.0413 (4) | 0.9358 (2) | 0.0629 (10) | |
H6A | 0.7590 | −0.0410 | 0.9743 | 0.075* | |
C7 | 0.7362 (5) | 0.0087 (4) | 0.8503 (2) | 0.0607 (9) | |
C8 | 0.8176 (5) | 0.1308 (4) | 0.7910 (2) | 0.0579 (9) | |
C9 | 0.9597 (5) | 0.2792 (4) | 0.8216 (2) | 0.0537 (8) | |
H9A | 1.0103 | 0.3620 | 0.7834 | 0.064* | |
C10 | 0.7439 (6) | 0.0996 (5) | 0.6984 (2) | 0.0790 (12) | |
H10A | 0.8184 | 0.1926 | 0.6672 | 0.119* | |
H10B | 0.6192 | 0.0889 | 0.6924 | 0.119* | |
H10C | 0.7471 | −0.0026 | 0.6767 | 0.119* | |
O3 | 0.2589 (4) | 0.2954 (3) | 0.47872 (15) | 0.0695 (7) | |
O4 | 0.1772 (4) | 0.3743 (3) | 0.59841 (17) | 0.0836 (9) | |
N2 | 0.2153 (5) | −0.3189 (4) | 0.69728 (19) | 0.0828 (11) | |
H2C | 0.1979 | −0.3380 | 0.7496 | 0.099* | |
H2D | 0.2337 | −0.3903 | 0.6656 | 0.099* | |
C11 | 0.3055 (7) | 0.4392 (6) | 0.3509 (3) | 0.0990 (15) | |
H11A | 0.3072 | 0.5370 | 0.3229 | 0.149* | |
H11B | 0.2152 | 0.3391 | 0.3204 | 0.149* | |
H11C | 0.4248 | 0.4375 | 0.3523 | 0.149* | |
C12 | 0.2570 (6) | 0.4456 (5) | 0.4406 (2) | 0.0764 (11) | |
H12A | 0.3465 | 0.5466 | 0.4722 | 0.092* | |
H12B | 0.1360 | 0.4461 | 0.4403 | 0.092* | |
C13 | 0.2119 (5) | 0.2726 (5) | 0.5596 (2) | 0.0608 (9) | |
C14 | 0.2194 (5) | 0.1199 (4) | 0.59291 (19) | 0.0543 (8) | |
C15 | 0.1854 (5) | 0.0871 (4) | 0.6782 (2) | 0.0545 (8) | |
H15A | 0.1632 | 0.1649 | 0.7108 | 0.065* | |
C16 | 0.1840 (5) | −0.0559 (4) | 0.7146 (2) | 0.0549 (8) | |
C17 | 0.2137 (5) | −0.1753 (4) | 0.6644 (2) | 0.0597 (9) | |
C18 | 0.2476 (6) | −0.1425 (5) | 0.5793 (2) | 0.0682 (11) | |
H18A | 0.2686 | −0.2200 | 0.5458 | 0.082* | |
C19 | 0.2499 (5) | 0.0029 (5) | 0.5451 (2) | 0.0660 (10) | |
H19A | 0.2724 | 0.0221 | 0.4887 | 0.079* | |
C20 | 0.1455 (6) | −0.0876 (5) | 0.8067 (2) | 0.0768 (12) | |
H20A | 0.1279 | 0.0055 | 0.8312 | 0.115* | |
H20B | 0.2479 | −0.0986 | 0.8379 | 0.115* | |
H20C | 0.0363 | −0.1897 | 0.8089 | 0.115* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0901 (18) | 0.0660 (16) | 0.0515 (14) | 0.0347 (14) | 0.0056 (13) | 0.0157 (12) |
O2 | 0.100 (2) | 0.0594 (15) | 0.0596 (16) | 0.0282 (14) | 0.0118 (14) | 0.0263 (13) |
N1 | 0.099 (3) | 0.072 (2) | 0.078 (2) | 0.021 (2) | 0.013 (2) | 0.0202 (18) |
C1 | 0.114 (4) | 0.099 (3) | 0.063 (3) | 0.059 (3) | −0.010 (2) | −0.008 (2) |
C2 | 0.090 (3) | 0.060 (2) | 0.067 (2) | 0.040 (2) | 0.000 (2) | 0.0075 (19) |
C3 | 0.068 (2) | 0.055 (2) | 0.051 (2) | 0.0334 (18) | 0.0094 (17) | 0.0118 (16) |
C4 | 0.068 (2) | 0.0485 (19) | 0.0467 (18) | 0.0319 (17) | 0.0108 (16) | 0.0142 (15) |
C5 | 0.087 (3) | 0.060 (2) | 0.048 (2) | 0.037 (2) | 0.0177 (18) | 0.0259 (17) |
C6 | 0.078 (3) | 0.057 (2) | 0.057 (2) | 0.030 (2) | 0.0191 (19) | 0.0255 (18) |
C7 | 0.072 (2) | 0.049 (2) | 0.067 (2) | 0.0285 (18) | 0.0145 (19) | 0.0180 (17) |
C8 | 0.073 (2) | 0.062 (2) | 0.049 (2) | 0.0373 (19) | 0.0100 (17) | 0.0149 (17) |
C9 | 0.073 (2) | 0.0505 (19) | 0.0439 (18) | 0.0305 (18) | 0.0133 (16) | 0.0173 (15) |
C10 | 0.096 (3) | 0.076 (3) | 0.056 (2) | 0.026 (2) | 0.006 (2) | 0.012 (2) |
O3 | 0.0994 (19) | 0.0705 (16) | 0.0524 (15) | 0.0462 (15) | 0.0200 (13) | 0.0246 (12) |
O4 | 0.140 (3) | 0.0684 (17) | 0.0626 (17) | 0.0603 (18) | 0.0224 (16) | 0.0110 (14) |
N2 | 0.148 (3) | 0.070 (2) | 0.0511 (18) | 0.065 (2) | 0.0102 (19) | 0.0136 (16) |
C11 | 0.135 (4) | 0.104 (4) | 0.066 (3) | 0.053 (3) | 0.022 (3) | 0.038 (3) |
C12 | 0.102 (3) | 0.068 (2) | 0.066 (3) | 0.041 (2) | 0.012 (2) | 0.027 (2) |
C13 | 0.077 (2) | 0.064 (2) | 0.047 (2) | 0.034 (2) | 0.0102 (17) | 0.0113 (17) |
C14 | 0.072 (2) | 0.055 (2) | 0.0380 (17) | 0.0288 (17) | 0.0062 (15) | 0.0088 (15) |
C15 | 0.079 (2) | 0.056 (2) | 0.0427 (18) | 0.0406 (18) | 0.0107 (16) | 0.0082 (15) |
C16 | 0.076 (2) | 0.061 (2) | 0.0390 (17) | 0.0380 (18) | 0.0113 (16) | 0.0099 (15) |
C17 | 0.094 (3) | 0.055 (2) | 0.0438 (19) | 0.045 (2) | 0.0064 (17) | 0.0099 (15) |
C18 | 0.117 (3) | 0.064 (2) | 0.0439 (19) | 0.057 (2) | 0.011 (2) | 0.0021 (17) |
C19 | 0.099 (3) | 0.069 (2) | 0.0382 (18) | 0.041 (2) | 0.0134 (18) | 0.0084 (17) |
C20 | 0.120 (3) | 0.095 (3) | 0.042 (2) | 0.068 (3) | 0.022 (2) | 0.0199 (19) |
O1—C3 | 1.351 (4) | O3—C13 | 1.362 (4) |
O1—C2 | 1.446 (4) | O3—C12 | 1.452 (4) |
O2—C3 | 1.232 (4) | O4—C13 | 1.207 (4) |
N1—C7 | 1.369 (5) | N2—C17 | 1.365 (4) |
N1—H1A | 0.8600 | N2—H2C | 0.8600 |
N1—H1B | 0.8600 | N2—H2D | 0.8600 |
C1—C2 | 1.503 (5) | C11—C12 | 1.513 (5) |
C1—H1C | 0.9600 | C11—H11A | 0.9600 |
C1—H1D | 0.9600 | C11—H11B | 0.9600 |
C1—H1E | 0.9600 | C11—H11C | 0.9600 |
C2—H2A | 0.9700 | C12—H12A | 0.9700 |
C2—H2B | 0.9700 | C12—H12B | 0.9700 |
C3—C4 | 1.432 (5) | C13—C14 | 1.458 (5) |
C4—C5 | 1.407 (4) | C14—C19 | 1.374 (5) |
C4—C9 | 1.409 (4) | C14—C15 | 1.411 (4) |
C5—C6 | 1.349 (5) | C15—C16 | 1.375 (4) |
C5—H5A | 0.9300 | C15—H15A | 0.9300 |
C6—C7 | 1.404 (5) | C16—C17 | 1.409 (4) |
C6—H6A | 0.9300 | C16—C20 | 1.522 (4) |
C7—C8 | 1.414 (5) | C17—C18 | 1.409 (4) |
C8—C9 | 1.367 (5) | C18—C19 | 1.376 (5) |
C8—C10 | 1.509 (5) | C18—H18A | 0.9300 |
C9—H9A | 0.9300 | C19—H19A | 0.9300 |
C10—H10A | 0.9600 | C20—H20A | 0.9600 |
C10—H10B | 0.9600 | C20—H20B | 0.9600 |
C10—H10C | 0.9600 | C20—H20C | 0.9600 |
C3—O1—C2 | 118.2 (3) | C13—O3—C12 | 116.0 (3) |
C7—N1—H1A | 120.0 | C17—N2—H2C | 120.0 |
C7—N1—H1B | 120.0 | C17—N2—H2D | 120.0 |
H1A—N1—H1B | 120.0 | H2C—N2—H2D | 120.0 |
C2—C1—H1C | 109.5 | C12—C11—H11A | 109.5 |
C2—C1—H1D | 109.5 | C12—C11—H11B | 109.5 |
H1C—C1—H1D | 109.5 | H11A—C11—H11B | 109.5 |
C2—C1—H1E | 109.5 | C12—C11—H11C | 109.5 |
H1C—C1—H1E | 109.5 | H11A—C11—H11C | 109.5 |
H1D—C1—H1E | 109.5 | H11B—C11—H11C | 109.5 |
O1—C2—C1 | 107.6 (3) | O3—C12—C11 | 106.2 (3) |
O1—C2—H2A | 110.2 | O3—C12—H12A | 110.5 |
C1—C2—H2A | 110.2 | C11—C12—H12A | 110.5 |
O1—C2—H2B | 110.2 | O3—C12—H12B | 110.5 |
C1—C2—H2B | 110.2 | C11—C12—H12B | 110.5 |
H2A—C2—H2B | 108.5 | H12A—C12—H12B | 108.7 |
O2—C3—O1 | 120.3 (3) | O4—C13—O3 | 121.9 (3) |
O2—C3—C4 | 126.2 (3) | O4—C13—C14 | 125.8 (3) |
O1—C3—C4 | 113.5 (3) | O3—C13—C14 | 112.2 (3) |
C5—C4—C9 | 116.4 (3) | C19—C14—C15 | 118.2 (3) |
C5—C4—C3 | 123.1 (3) | C19—C14—C13 | 123.8 (3) |
C9—C4—C3 | 120.5 (3) | C15—C14—C13 | 118.0 (3) |
C6—C5—C4 | 121.0 (3) | C16—C15—C14 | 122.3 (3) |
C6—C5—H5A | 119.5 | C16—C15—H15A | 118.8 |
C4—C5—H5A | 119.5 | C14—C15—H15A | 118.8 |
C5—C6—C7 | 121.8 (3) | C15—C16—C17 | 118.7 (3) |
C5—C6—H6A | 119.1 | C15—C16—C20 | 120.9 (3) |
C7—C6—H6A | 119.1 | C17—C16—C20 | 120.4 (3) |
N1—C7—C6 | 121.1 (3) | N2—C17—C16 | 121.3 (3) |
N1—C7—C8 | 119.7 (3) | N2—C17—C18 | 119.7 (3) |
C6—C7—C8 | 119.1 (3) | C16—C17—C18 | 119.0 (3) |
C9—C8—C7 | 117.5 (3) | C19—C18—C17 | 120.8 (3) |
C9—C8—C10 | 121.9 (3) | C19—C18—H18A | 119.6 |
C7—C8—C10 | 120.6 (3) | C17—C18—H18A | 119.6 |
C8—C9—C4 | 124.2 (3) | C14—C19—C18 | 121.0 (3) |
C8—C9—H9A | 117.9 | C14—C19—H19A | 119.5 |
C4—C9—H9A | 117.9 | C18—C19—H19A | 119.5 |
C8—C10—H10A | 109.5 | C16—C20—H20A | 109.5 |
C8—C10—H10B | 109.5 | C16—C20—H20B | 109.5 |
H10A—C10—H10B | 109.5 | H20A—C20—H20B | 109.5 |
C8—C10—H10C | 109.5 | C16—C20—H20C | 109.5 |
H10A—C10—H10C | 109.5 | H20A—C20—H20C | 109.5 |
H10B—C10—H10C | 109.5 | H20B—C20—H20C | 109.5 |
C3—O1—C2—C1 | 178.1 (3) | C13—O3—C12—C11 | −177.7 (3) |
C2—O1—C3—O2 | 1.4 (5) | C12—O3—C13—O4 | −2.5 (5) |
C2—O1—C3—C4 | 179.7 (3) | C12—O3—C13—C14 | −179.4 (3) |
O2—C3—C4—C5 | −176.4 (3) | O4—C13—C14—C19 | 176.4 (4) |
O1—C3—C4—C5 | 5.4 (5) | O3—C13—C14—C19 | −6.9 (5) |
O2—C3—C4—C9 | 2.0 (5) | O4—C13—C14—C15 | −0.8 (6) |
O1—C3—C4—C9 | −176.2 (3) | O3—C13—C14—C15 | 176.0 (3) |
C9—C4—C5—C6 | 1.4 (5) | C19—C14—C15—C16 | 0.8 (5) |
C3—C4—C5—C6 | 179.9 (3) | C13—C14—C15—C16 | 178.1 (3) |
C4—C5—C6—C7 | −1.9 (6) | C14—C15—C16—C17 | −1.4 (5) |
C5—C6—C7—N1 | 179.2 (4) | C14—C15—C16—C20 | −179.6 (3) |
C5—C6—C7—C8 | 2.7 (6) | C15—C16—C17—N2 | 179.5 (4) |
N1—C7—C8—C9 | −179.6 (3) | C20—C16—C17—N2 | −2.3 (6) |
C6—C7—C8—C9 | −3.0 (5) | C15—C16—C17—C18 | 1.3 (5) |
N1—C7—C8—C10 | 2.9 (5) | C20—C16—C17—C18 | 179.5 (4) |
C6—C7—C8—C10 | 179.4 (3) | N2—C17—C18—C19 | −178.9 (4) |
C7—C8—C9—C4 | 2.8 (5) | C16—C17—C18—C19 | −0.7 (6) |
C10—C8—C9—C4 | −179.7 (3) | C15—C14—C19—C18 | −0.1 (6) |
C5—C4—C9—C8 | −2.0 (5) | C13—C14—C19—C18 | −177.2 (4) |
C3—C4—C9—C8 | 179.6 (3) | C17—C18—C19—C14 | 0.0 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2i | 0.86 | 2.33 | 3.023 (5) | 138 |
N1—H1B···N2 | 0.86 | 2.61 | 3.242 (5) | 131 |
N2—H2C···O2i | 0.86 | 2.35 | 3.160 (4) | 157 |
N2—H2D···O4ii | 0.86 | 2.15 | 2.967 (4) | 158 |
Symmetry codes: (i) x−1, y−1, z; (ii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C10H13NO2 |
Mr | 179.21 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 8.0110 (16), 8.7030 (17), 15.835 (3) |
α, β, γ (°) | 90.78 (3), 95.13 (3), 114.34 (3) |
V (Å3) | 1000.3 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.30 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.975, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3874, 3594, 2146 |
Rint | 0.052 |
(sin θ/λ)max (Å−1) | 0.598 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.075, 0.177, 1.02 |
No. of reflections | 3594 |
No. of parameters | 235 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.23 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4(Harms & Wocadlo,1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2i | 0.86 | 2.33 | 3.023 (5) | 138 |
N1—H1B···N2 | 0.86 | 2.61 | 3.242 (5) | 131 |
N2—H2C···O2i | 0.86 | 2.35 | 3.160 (4) | 157 |
N2—H2D···O4ii | 0.86 | 2.15 | 2.967 (4) | 158 |
Symmetry codes: (i) x−1, y−1, z; (ii) x, y−1, z. |
Acknowledgements
The authors thank Dr Shan Liu for useful discussions.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Ethyl 3-methyl-4-aminobenzoate is a material for preparing the important intermidates of bis-(2-haloethyl)aminophenyl substituted distamycin derivatives(Baraldi et al., 2007), which are used as antitumor alkylating and antiviral agents related to the known antibiotic distamycin A (Baraldi et al., 1999). Distamycin A belongs to the family of the pyrroleamidine antibiotics (Baraldi et al., 2000) and is reported to interact reversibly and selectively with DNA-AT sequences interfering with both replication and transcription (Baraldi et al., 2003). Bis-(2-haloethyl)aminophenyl substituted distamycin derivatives can therefore be used in a treatment to ameliorate a cancer (Wang et al., 2003). They may be administered to improve the condition of a patient having a leukaemia lymphoma, sarcoma, such as myeloblastic leukaemia, neuroblastoma, Wilm's tumor or malignant neoplasm of the bladder, breast, lung or thyroid. (Zaffaroni et al., 2002).
The molecular structure of (I) is shown in Fig. 1. The bond lengths and angles are within normal ranges (Allen et al., 1987).
The asymmetric unit of the title compound, contains two molecules which are linked via N—H···N hydrogen bonds to form dimers. In the crystals, molecules are linked via N—H···O Intermolecular hydrogen bonds (Table 1), which may be effective in the stabilization of the crystals.