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We present here the crystal structure of the title compound, C
14H
19NO
4. It contains O
H—O and N
H—O hydrogen bonds, connecting the molecules into centrosymmetric dimers and into infinite chains.
Supporting information
CCDC reference: 202980
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.050
- wR factor = 0.128
- Data-to-parameter ratio = 15.1
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: KappaCCD Software (Nonius, 1997); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), PLATON (Spek, 2001); software used to prepare material for publication: maXus (Mackay et al., 1999).
[2-(tertbutylcarbonylmethyl-amino]-phenyl)acetic acid
top
Crystal data top
C14H19NO4 | F(000) = 568 |
Mr = 265.31 | Dx = 1.262 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8934 reflections |
a = 12.6392 (6) Å | θ = 1.0–26.2° |
b = 5.1470 (2) Å | µ = 0.09 mm−1 |
c = 22.5450 (1) Å | T = 293 K |
β = 107.744 (3)° | Prism, colourless |
V = 1396.85 (9) Å3 | 0.40 × 0.30 × 0.20 mm |
Z = 4 | |
Data collection top
Nonius Kappa CCD area-detector diffractometer | Rint = 0.033 |
Radiation source: X-ray tube | θmax = 26.2°, θmin = 1.0° |
φ–scan | h = −15→15 |
8934 measured reflections | k = −6→6 |
2702 independent reflections | l = −27→26 |
2362 reflections with I > 2σ(I) | |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0479P)2 + 0.4704P] where P = (Fo2 + 2Fc2)/3 |
2702 reflections | (Δ/σ)max < 0.001 |
179 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.93632 (12) | 0.7227 (3) | 0.01454 (7) | 0.0709 (4) | |
H1 | 0.9711 | 0.7984 | −0.0056 | 0.106* | 0.50 |
O2 | 0.96251 (14) | 1.0957 (3) | 0.06496 (8) | 0.0801 (5) | |
H2 | 1.0017 | 1.1232 | 0.0426 | 0.120* | 0.50 |
O3 | 0.65702 (11) | 0.4085 (2) | −0.02758 (6) | 0.0573 (3) | |
O4 | 0.68129 (11) | 0.7224 (2) | −0.09290 (5) | 0.0558 (3) | |
N1 | 0.66066 (11) | 0.8346 (2) | −0.00270 (6) | 0.0443 (3) | |
H1A | 0.6734 | 0.9895 | −0.0131 | 0.053* | |
C1 | 0.92836 (12) | 0.8667 (3) | 0.05778 (7) | 0.0472 (4) | |
C2 | 0.88080 (14) | 0.7487 (3) | 0.10508 (8) | 0.0532 (4) | |
H2A | 0.9410 | 0.6765 | 0.1387 | 0.064* | |
H2B | 0.8320 | 0.6067 | 0.0857 | 0.064* | |
C3 | 0.81681 (12) | 0.9378 (3) | 0.13197 (7) | 0.0432 (4) | |
C4 | 0.87278 (14) | 1.0978 (4) | 0.18132 (8) | 0.0575 (4) | |
H4 | 0.9495 | 1.0827 | 0.1980 | 0.069* | |
C5 | 0.81749 (16) | 1.2782 (4) | 0.20624 (8) | 0.0603 (5) | |
H5 | 0.8567 | 1.3834 | 0.2391 | 0.072* | |
C6 | 0.70477 (15) | 1.3012 (3) | 0.18230 (8) | 0.0554 (4) | |
H6 | 0.6668 | 1.4228 | 0.1987 | 0.067* | |
C7 | 0.64760 (13) | 1.1431 (3) | 0.13375 (7) | 0.0480 (4) | |
H7 | 0.5708 | 1.1586 | 0.1180 | 0.058* | |
C8 | 0.70146 (12) | 0.9614 (3) | 0.10768 (6) | 0.0395 (3) | |
C9 | 0.63389 (13) | 0.7940 (3) | 0.05497 (7) | 0.0484 (4) | |
H9A | 0.6464 | 0.6129 | 0.0670 | 0.058* | |
H9B | 0.5557 | 0.8307 | 0.0478 | 0.058* | |
C10 | 0.66578 (12) | 0.6345 (3) | −0.04007 (7) | 0.0414 (3) | |
C11 | 0.69455 (16) | 0.5403 (3) | −0.14067 (7) | 0.0548 (4) | |
C13 | 0.79464 (15) | 0.3713 (4) | −0.11459 (10) | 0.0657 (5) | |
H13A | 0.8575 | 0.4778 | −0.0941 | 0.099* | |
H13B | 0.8097 | 0.2765 | −0.1478 | 0.099* | |
H13C | 0.7808 | 0.2516 | −0.0852 | 0.099* | |
C14 | 0.58955 (17) | 0.3837 (5) | −0.16651 (11) | 0.0872 (8) | |
H14A | 0.5820 | 0.2637 | −0.1354 | 0.131* | |
H14B | 0.5932 | 0.2893 | −0.2026 | 0.131* | |
H14C | 0.5267 | 0.4984 | −0.1779 | 0.131* | |
C12 | 0.7136 (4) | 0.7221 (5) | −0.18916 (12) | 0.1299 (14) | |
H12A | 0.6523 | 0.8408 | −0.2027 | 0.195* | |
H12B | 0.7194 | 0.6230 | −0.2241 | 0.195* | |
H12C | 0.7810 | 0.8178 | −0.1714 | 0.195* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0783 (9) | 0.0742 (9) | 0.0779 (9) | −0.0137 (7) | 0.0500 (7) | −0.0223 (7) |
O2 | 0.1081 (12) | 0.0659 (9) | 0.0912 (10) | −0.0227 (8) | 0.0675 (9) | −0.0195 (7) |
O3 | 0.0839 (9) | 0.0309 (6) | 0.0639 (7) | −0.0030 (5) | 0.0329 (6) | 0.0014 (5) |
O4 | 0.1015 (9) | 0.0299 (5) | 0.0403 (6) | 0.0068 (5) | 0.0280 (6) | −0.0009 (4) |
N1 | 0.0643 (8) | 0.0317 (6) | 0.0406 (6) | 0.0000 (5) | 0.0214 (6) | −0.0005 (5) |
C1 | 0.0402 (7) | 0.0522 (9) | 0.0535 (9) | 0.0065 (6) | 0.0206 (6) | −0.0037 (7) |
C2 | 0.0520 (9) | 0.0547 (10) | 0.0584 (9) | 0.0144 (7) | 0.0250 (7) | 0.0105 (8) |
C3 | 0.0472 (8) | 0.0473 (8) | 0.0399 (7) | 0.0040 (6) | 0.0202 (6) | 0.0080 (6) |
C4 | 0.0505 (9) | 0.0756 (12) | 0.0459 (8) | −0.0022 (8) | 0.0139 (7) | 0.0003 (8) |
C5 | 0.0734 (11) | 0.0688 (12) | 0.0420 (8) | −0.0128 (9) | 0.0225 (8) | −0.0105 (8) |
C6 | 0.0736 (11) | 0.0555 (10) | 0.0465 (8) | 0.0049 (8) | 0.0321 (8) | −0.0046 (7) |
C7 | 0.0508 (8) | 0.0539 (9) | 0.0454 (8) | 0.0067 (7) | 0.0238 (7) | 0.0030 (7) |
C8 | 0.0467 (7) | 0.0400 (7) | 0.0368 (7) | 0.0010 (6) | 0.0205 (6) | 0.0059 (6) |
C9 | 0.0529 (8) | 0.0509 (9) | 0.0471 (8) | −0.0069 (7) | 0.0239 (7) | −0.0016 (7) |
C10 | 0.0491 (8) | 0.0325 (7) | 0.0420 (7) | 0.0018 (6) | 0.0131 (6) | 0.0007 (6) |
C11 | 0.0889 (12) | 0.0348 (8) | 0.0424 (8) | 0.0078 (8) | 0.0228 (8) | −0.0058 (6) |
C13 | 0.0606 (10) | 0.0680 (12) | 0.0697 (12) | 0.0021 (9) | 0.0217 (9) | −0.0203 (9) |
C14 | 0.0681 (12) | 0.0978 (17) | 0.0797 (14) | 0.0173 (11) | −0.0014 (10) | −0.0465 (13) |
C12 | 0.299 (5) | 0.0525 (13) | 0.0706 (14) | 0.0178 (19) | 0.105 (2) | 0.0019 (11) |
Geometric parameters (Å, º) top
O1—C1 | 1.253 (2) | C3—C8 | 1.398 (2) |
O2—C1 | 1.248 (2) | C4—C5 | 1.380 (3) |
O3—C10 | 1.2097 (18) | C5—C6 | 1.366 (3) |
O4—C10 | 1.3431 (18) | C6—C7 | 1.378 (2) |
O4—C11 | 1.4753 (18) | C7—C8 | 1.388 (2) |
N1—C10 | 1.3447 (19) | C8—C9 | 1.505 (2) |
N1—C9 | 1.4549 (19) | C11—C13 | 1.500 (3) |
C1—C2 | 1.503 (2) | C11—C14 | 1.510 (3) |
C2—C3 | 1.506 (2) | C11—C12 | 1.513 (3) |
C3—C4 | 1.391 (2) | | |
| | | |
C10—O4—C11 | 120.87 (12) | C7—C8—C3 | 118.69 (14) |
C10—N1—C9 | 121.24 (13) | C7—C8—C9 | 119.11 (14) |
O2—C1—O1 | 123.55 (16) | C3—C8—C9 | 122.20 (13) |
O2—C1—C2 | 119.14 (15) | N1—C9—C8 | 113.12 (12) |
O1—C1—C2 | 117.21 (15) | O3—C10—O4 | 125.37 (14) |
C1—C2—C3 | 113.84 (13) | O3—C10—N1 | 124.43 (14) |
C4—C3—C8 | 118.52 (14) | O4—C10—N1 | 110.21 (12) |
C4—C3—C2 | 119.98 (14) | O4—C11—C13 | 110.61 (14) |
C8—C3—C2 | 121.49 (14) | O4—C11—C14 | 109.80 (15) |
C5—C4—C3 | 121.75 (16) | C13—C11—C14 | 112.27 (16) |
C6—C5—C4 | 119.60 (16) | O4—C11—C12 | 102.30 (13) |
C5—C6—C7 | 119.58 (15) | C13—C11—C12 | 110.0 (2) |
C6—C7—C8 | 121.86 (15) | C14—C11—C12 | 111.5 (2) |
| | | |
O2—C1—C2—C3 | 35.3 (2) | C4—C3—C8—C9 | −179.09 (14) |
O1—C1—C2—C3 | −148.17 (16) | C2—C3—C8—C9 | 2.2 (2) |
C1—C2—C3—C4 | −83.50 (19) | C10—N1—C9—C8 | 140.35 (14) |
C1—C2—C3—C8 | 95.20 (18) | C7—C8—C9—N1 | 117.26 (15) |
C8—C3—C4—C5 | −0.4 (2) | C3—C8—C9—N1 | −63.65 (19) |
C2—C3—C4—C5 | 178.35 (16) | C11—O4—C10—O3 | −3.0 (2) |
C3—C4—C5—C6 | 0.2 (3) | C11—O4—C10—N1 | 177.38 (14) |
C4—C5—C6—C7 | 0.3 (3) | C9—N1—C10—O3 | −5.5 (2) |
C5—C6—C7—C8 | −0.7 (2) | C9—N1—C10—O4 | 174.17 (13) |
C6—C7—C8—C3 | 0.5 (2) | C10—O4—C11—C13 | −61.0 (2) |
C6—C7—C8—C9 | 179.67 (14) | C10—O4—C11—C14 | 63.5 (2) |
C4—C3—C8—C7 | 0.0 (2) | C10—O4—C11—C12 | −178.0 (2) |
C2—C3—C8—C7 | −178.72 (13) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.82 | 1.86 | 2.668 (2) | 166 |
O2—H2···O1i | 0.82 | 1.87 | 2.668 (2) | 162 |
N1—H1A···O3ii | 0.86 | 2.18 | 3.004 (2) | 160 |
Symmetry codes: (i) −x+2, −y+2, −z; (ii) x, y+1, z. |
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