organic compounds
The structure of the title compound, C9H11NO2, (I), comprises a flat molecule arranged, head-to-tail, in linear ribbon arrays via a N—HO=C association. These ribbons end-on form a herring-bone structure interconnected via N—HN association. The structure was first determined in 1987 [Sinha & Pattabhi (1987). Proc. Indian Acad. Sci. Chem. Sci. 98, 229–234] in the orthorhombic space group P212121, with R = 0.120, whereas similar cell dimensions and an increased β angle in the present study resulted in monoclinic space group P21/c, with R = 0.065.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802009674/cv6118sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802009674/cv6118Isup2.hkl |
CCDC reference: 189882
Computing details top
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.
Ethyl 4-aminobenzoate top
Crystal data top
C9H11NO2 | F(000) = 352 |
Mr = 165.19 | Dx = 1.259 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.198 (2) Å | Cell parameters from 3445 reflections |
b = 5.430 (1) Å | θ = 1.0–27.5° |
c = 19.592 (5) Å | µ = 0.09 mm−1 |
β = 91.350 (6)° | T = 120 K |
V = 871.8 (4) Å3 | Block, colourless |
Z = 4 | 0.10 × 0.08 × 0.03 mm |
Data collection top
Bruker–Nonius KappaCCD area-detector diffractometer | 1352 independent reflections |
Radiation source: Bruker–Nonius FR591 rotating anode | 686 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.097 |
Detector resolution: 9.091 pixels mm-1 | θmax = 25.0°, θmin = 2.1° |
φ and ω scans | h = −9→9 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −6→5 |
Tmin = 0.991, Tmax = 0.997 | l = −21→23 |
3445 measured reflections |
Refinement top
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)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.181 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0712P)2] where P = (Fo2 + 2Fc2)/3 |
1352 reflections | (Δ/σ)max < 0.001 |
110 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.7720 (3) | 0.4029 (5) | 0.3662 (1) | 0.0403 (9) | |
O2 | 0.6328 (3) | 0.6836 (5) | 0.4257 (1) | 0.0364 (8) | |
N1 | 0.0252 (4) | 0.1297 (6) | 0.2947 (2) | 0.0384 (10) | |
H11 | −0.0644 | 0.2087 | 0.3054 | 0.048* | |
H12 | 0.0190 | −0.0053 | 0.2699 | 0.048* | |
C1 | 0.4808 (4) | 0.3984 (7) | 0.3602 (2) | 0.0284 (10) | |
C2 | 0.4679 (5) | 0.1868 (7) | 0.3205 (2) | 0.0323 (11) | |
H2 | 0.5643 | 0.1024 | 0.3081 | 0.040* | |
C3 | 0.3180 (4) | 0.0967 (7) | 0.2987 (2) | 0.0321 (11) | |
H3 | 0.3124 | −0.0476 | 0.2714 | 0.040* | |
C4 | 0.1747 (5) | 0.2170 (7) | 0.3168 (2) | 0.0287 (10) | |
C5 | 0.1861 (5) | 0.4297 (8) | 0.3560 (2) | 0.0340 (11) | |
H5 | 0.0896 | 0.5142 | 0.3682 | 0.042* | |
C6 | 0.3370 (4) | 0.5200 (7) | 0.3775 (2) | 0.0322 (11) | |
H6 | 0.3428 | 0.6658 | 0.4042 | 0.040* | |
C7 | 0.6417 (5) | 0.4910 (7) | 0.3831 (2) | 0.0331 (11) | |
C8 | 0.7868 (5) | 0.7847 (8) | 0.4499 (2) | 0.0404 (12) | |
H71 | 0.8485 | 0.8526 | 0.4113 | 0.050* | |
H72 | 0.8538 | 0.6557 | 0.4727 | 0.050* | |
C9 | 0.7458 (5) | 0.9862 (7) | 0.4998 (2) | 0.0401 (12) | |
H73 | 0.6718 | 1.1048 | 0.4775 | 0.050* | |
H74 | 0.8462 | 1.0702 | 0.5148 | 0.050* | |
H75 | 0.6928 | 0.9141 | 0.5394 | 0.050* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0234 (19) | 0.047 (2) | 0.050 (2) | 0.0006 (15) | 0.0047 (14) | −0.0056 (15) |
O2 | 0.0260 (17) | 0.0366 (18) | 0.0464 (19) | −0.0046 (13) | −0.0018 (13) | −0.0087 (15) |
N1 | 0.023 (2) | 0.041 (2) | 0.050 (2) | 0.0043 (16) | −0.0014 (16) | −0.0106 (18) |
C1 | 0.022 (2) | 0.027 (3) | 0.036 (3) | 0.0003 (18) | 0.0008 (18) | 0.0029 (19) |
C2 | 0.026 (3) | 0.038 (3) | 0.032 (3) | 0.006 (2) | 0.0066 (18) | 0.002 (2) |
C3 | 0.025 (3) | 0.030 (3) | 0.041 (3) | −0.0025 (19) | 0.001 (2) | −0.0021 (19) |
C4 | 0.022 (2) | 0.028 (3) | 0.036 (3) | −0.0027 (19) | −0.0016 (18) | 0.002 (2) |
C5 | 0.025 (3) | 0.031 (3) | 0.045 (3) | 0.0020 (19) | 0.002 (2) | −0.001 (2) |
C6 | 0.026 (3) | 0.028 (3) | 0.043 (3) | 0.0013 (19) | −0.0011 (19) | −0.0017 (19) |
C7 | 0.028 (3) | 0.033 (3) | 0.038 (3) | −0.003 (2) | 0.001 (2) | 0.001 (2) |
C8 | 0.023 (3) | 0.053 (3) | 0.045 (3) | −0.010 (2) | 0.001 (2) | −0.001 (2) |
C9 | 0.029 (3) | 0.045 (3) | 0.047 (3) | −0.004 (2) | −0.005 (2) | −0.005 (2) |
Geometric parameters (Å, º) top
O1—C7 | 1.223 (4) | C3—H3 | 0.95 |
O2—C7 | 1.341 (5) | C4—C5 | 1.389 (5) |
O2—C8 | 1.446 (4) | C5—C6 | 1.387 (5) |
N1—C4 | 1.374 (4) | C5—H5 | 0.95 |
N1—H11 | 0.88 | C6—H6 | 0.95 |
N1—H12 | 0.88 | C8—C9 | 1.511 (5) |
C1—C2 | 1.389 (5) | C8—H71 | 0.99 |
C1—C6 | 1.400 (5) | C8—H72 | 0.99 |
C1—C7 | 1.472 (5) | C9—H73 | 0.98 |
C2—C3 | 1.381 (5) | C9—H74 | 0.98 |
C2—H2 | 0.95 | C9—H75 | 0.98 |
C3—C4 | 1.397 (5) | ||
C7—O2—C8 | 116.1 (3) | C5—C6—C1 | 120.6 (4) |
C4—N1—H11 | 120.0 | C5—C6—H6 | 119.7 |
C4—N1—H12 | 120.0 | C1—C6—H6 | 119.7 |
H11—N1—H12 | 120.0 | O1—C7—O2 | 122.2 (4) |
C2—C1—C6 | 118.2 (3) | O1—C7—C1 | 124.5 (4) |
C2—C1—C7 | 120.6 (4) | O2—C7—C1 | 113.3 (4) |
C6—C1—C7 | 121.2 (4) | O2—C8—C9 | 106.3 (3) |
C3—C2—C1 | 121.4 (4) | O2—C8—H71 | 110.5 |
C3—C2—H2 | 119.3 | C9—C8—H71 | 110.5 |
C1—C2—H2 | 119.3 | O2—C8—H72 | 110.5 |
C2—C3—C4 | 120.3 (4) | C9—C8—H72 | 110.5 |
C2—C3—H3 | 119.9 | H71—C8—H72 | 108.7 |
C4—C3—H3 | 119.9 | C8—C9—H73 | 109.5 |
N1—C4—C5 | 120.6 (4) | C8—C9—H74 | 109.5 |
N1—C4—C3 | 120.5 (4) | H73—C9—H74 | 109.5 |
C5—C4—C3 | 118.8 (3) | C8—C9—H75 | 109.5 |
C6—C5—C4 | 120.7 (4) | H73—C9—H75 | 109.5 |
C6—C5—H5 | 119.7 | H74—C9—H75 | 109.5 |
C4—C5—H5 | 119.7 | ||
C6—C1—C2—C3 | −0.3 (5) | C7—C1—C6—C5 | −179.5 (4) |
C7—C1—C2—C3 | 179.8 (4) | C8—O2—C7—O1 | 1.1 (5) |
C1—C2—C3—C4 | −0.5 (6) | C8—O2—C7—C1 | −179.6 (3) |
C2—C3—C4—N1 | 179.3 (3) | C2—C1—C7—O1 | 4.8 (6) |
C2—C3—C4—C5 | 0.9 (5) | C6—C1—C7—O1 | −175.2 (4) |
N1—C4—C5—C6 | −179.1 (4) | C2—C1—C7—O2 | −174.5 (3) |
C3—C4—C5—C6 | −0.7 (6) | C6—C1—C7—O2 | 5.5 (5) |
C4—C5—C6—C1 | 0.0 (6) | C7—O2—C8—C9 | −176.6 (3) |
C2—C1—C6—C5 | 0.5 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O1i | 0.88 | 2.10 | 2.934 (4) | 158 |
N1—H12···N1ii | 0.88 | 2.38 | 3.252 (3) | 174 |
Symmetry codes: (i) x−1, y, z; (ii) −x, y−1/2, −z+1/2. |