[2-(tert­-Butyl­carbonyl­methylamino)phenyl]­acetic acid

We present here the crystal structure of the title comp­ound, C₁₄H₁₉NO₄. It contains O...H—O and N...H—O hydrogen bonds, connecting the mol­ecules into centrosymmetric dimers and into infinite chains.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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

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Computing details

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

Crystal data

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) Å^3	0.40 × 0.30 × 0.20 mm
Z = 4

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.128	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0479P)^2 + 0.4704P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.82	1.86	2.668 (2)	166
O2—H2···O1^i	0.82	1.87	2.668 (2)	162
N1—H1A···O3^ii	0.86	2.18	3.004 (2)	160

Symmetry codes: (i) −x+2, −y+2, −z; (ii) x, y+1, z.