Methyl 2-[(tert-but­oxy­carbon­yl)amino]-3-(4-hy­droxy­phen­yl)propano­ate

Li, X.

doi:10.1107/S160053681301979X

organic compounds

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Volume 69| Part 9| September 2013| Page o1372

doi:10.1107/S160053681301979X

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Methyl 2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoate

Xiaokun Li ^a ^*

^aCollege of Pharmacy, Henan University of Traditional Chinese Medicine, Zhengzhou 450046, People's Republic of China
^*Correspondence e-mail: li96052122@126.com

(Received 6 July 2013; accepted 17 July 2013; online 3 August 2013)

In the title molecule, C₁₅H₂₁NO₅, the dihedral angle between the mean plane of the –N—C(=O)—O– group [maximum deviation = 0.002 (1) Å for the C atom] and the benzene ring is 82.2 (2)°. In the crystal, O—H⋯O and N—H⋯O hydrogen bonds connect the molecules, forming a two-dimensional network parallel to (001).

Related literature

For the biological activity of related compounds, see: Sykes et al. (1999 ).

Experimental

Crystal data

C₁₅H₂₁NO₅
M_r = 295.33
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.7879 (8) Å
b = 9.4844 (9) Å
c = 18.9207 (18) Å
V = 1577.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.55 × 0.49 × 0.45 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.962, T_max = 0.989
9339 measured reflections
3636 independent reflections
3469 reflections with I > 2σ(I)
R_int = 0.072

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.102
S = 1.03
3636 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O3ⁱ	0.86	2.27	3.0583 (16)	153
O1—H1C⋯O5ⁱⁱ	0.82	1.92	2.7356 (15)	180
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (ii) x, y+1, z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007)'; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681301979X/lh5632sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681301979X/lh5632Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681301979X/lh5632Isup3.cml

checkCIF report

Comment top

Amide, ester and hydroxyl groups widely exist in many biologically active compounds or can be utilized in prodrugs (Sykes et al., 1999). Herein we report the crystal structure of the title compound. The dihedral angle between the mean-plane of the amide group (N1/C9/O5/O4) [a maximum deviation of 0.002 (1)° for C9) and the benzene ring (C1–C6) is 82.2 (2)°. In the crystal, O—H···O and N—H···O hydrogen bonds connect molecules forming a two-dimensional network parallel to (001) (Fig. 2).

Related literature top

For the biological activity of related compounds, see: Sykes et al. (1999).

Experimental top

The title compound (0.3 mmol, 88.5 mg) was dissolved in 10 ml of methanol solution. Colorless block-shaped crystals separated after 5 d.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); data reduction: SAINT (Bruker, 2007)'; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular strcuture of the title compound with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Part of the crystal structure with hydrogen bonds shown as dashed lines. H atoms bonded to C atoms are not shown.

Methyl 2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoate top

Crystal data top

C₁₅H₂₁NO₅	F(000) = 632
M_r = 295.33	D_x = 1.244 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9371 reflections
a = 8.7879 (8) Å	θ = 1.0–27.6°
b = 9.4844 (9) Å	µ = 0.09 mm⁻¹
c = 18.9207 (18) Å	T = 100 K
V = 1577.0 (3) Å³	Block, colourless
Z = 4	0.55 × 0.49 × 0.45 mm

Data collection top

Bruker APEXII CCD diffractometer	3636 independent reflections
Radiation source: fine-focus sealed tube	3469 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.072
ϕ and ω scans	θ_max = 27.6°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→9
T_min = 0.962, T_max = 0.989	k = −12→8
9339 measured reflections	l = −24→24

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0581P)² + 0.1712P] where P = (F_o² + 2F_c²)/3
3636 reflections	(Δ/σ)_max = 0.008
190 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₅H₂₁NO₅	V = 1577.0 (3) Å³
M_r = 295.33	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.7879 (8) Å	µ = 0.09 mm⁻¹
b = 9.4844 (9) Å	T = 100 K
c = 18.9207 (18) Å	0.55 × 0.49 × 0.45 mm

Data collection top

Bruker APEXII CCD diffractometer	3636 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3469 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.989	R_int = 0.072
9339 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.03	Δρ_max = 0.32 e Å⁻³
3636 reflections	Δρ_min = −0.20 e Å⁻³
190 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	U_iso*/U_eq
C1	−0.04196 (17)	1.13511 (15)	0.18071 (7)	0.0216 (3)
H1A	−0.1123	1.1434	0.2172	0.026*
C2	−0.03335 (16)	1.01206 (15)	0.14197 (7)	0.0205 (3)
H2A	−0.0978	0.9376	0.1531	0.025*
C3	0.07017 (15)	0.99675 (14)	0.08627 (7)	0.0172 (3)
C4	0.16908 (15)	1.10800 (15)	0.07254 (7)	0.0192 (3)
H4A	0.2409	1.0991	0.0367	0.023*
C5	0.16250 (16)	1.23229 (15)	0.11142 (7)	0.0200 (3)
H5A	0.2297	1.3055	0.1016	0.024*
C6	0.05528 (16)	1.24689 (14)	0.16488 (7)	0.0184 (3)
C7	0.06700 (17)	0.86702 (15)	0.04022 (7)	0.0188 (3)
H7A	0.1336	0.8823	0.0001	0.023*
H7B	−0.0354	0.8547	0.0221	0.023*
C8	0.11575 (14)	0.73007 (14)	0.07772 (7)	0.0166 (3)
H8A	0.0573	0.7217	0.1216	0.020*
C9	0.33960 (15)	0.64306 (14)	0.13963 (7)	0.0159 (3)
C10	0.59030 (15)	0.56854 (15)	0.18449 (7)	0.0199 (3)
C11	0.5429 (2)	0.5555 (2)	0.26171 (8)	0.0302 (3)
H11A	0.5434	0.6471	0.2833	0.045*
H11B	0.6131	0.4950	0.2861	0.045*
H11C	0.4424	0.5161	0.2644	0.045*
C12	0.59178 (18)	0.42703 (17)	0.14678 (8)	0.0280 (3)
H12A	0.6225	0.4403	0.0985	0.042*
H12B	0.4917	0.3866	0.1480	0.042*
H12C	0.6621	0.3649	0.1699	0.042*
C13	0.74355 (17)	0.64103 (19)	0.17817 (9)	0.0305 (3)
H13A	0.7714	0.6480	0.1292	0.046*
H13B	0.8190	0.5872	0.2030	0.046*
H13C	0.7373	0.7338	0.1982	0.046*
C14	0.1469 (2)	0.42237 (17)	−0.04498 (8)	0.0292 (3)
H14A	0.2370	0.3749	−0.0609	0.044*
H14B	0.0943	0.4618	−0.0848	0.044*
H14C	0.0816	0.3563	−0.0213	0.044*
C15	0.07176 (16)	0.60783 (14)	0.02939 (7)	0.0180 (3)
N1	0.27499 (13)	0.73700 (12)	0.09567 (6)	0.0170 (2)
H1B	0.3301	0.8029	0.0778	0.020*
O1	0.04029 (13)	1.36708 (11)	0.20398 (5)	0.0247 (2)
H1C	0.1090	1.4220	0.1939	0.037*
O2	0.18880 (11)	0.53485 (11)	0.00379 (5)	0.0221 (2)
O3	−0.05943 (13)	0.58394 (11)	0.01458 (6)	0.0254 (2)
O4	0.48955 (11)	0.66726 (10)	0.14566 (5)	0.0186 (2)
O5	0.27010 (12)	0.54940 (10)	0.16994 (5)	0.0204 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0215 (7)	0.0263 (7)	0.0171 (6)	−0.0023 (6)	0.0044 (5)	0.0007 (5)
C2	0.0205 (6)	0.0205 (6)	0.0206 (6)	−0.0054 (5)	0.0015 (5)	0.0015 (5)
C3	0.0161 (6)	0.0182 (6)	0.0172 (6)	0.0019 (5)	−0.0039 (5)	0.0011 (5)
C4	0.0145 (6)	0.0235 (7)	0.0195 (6)	0.0009 (5)	0.0020 (5)	0.0009 (5)
C5	0.0176 (6)	0.0208 (6)	0.0217 (6)	−0.0034 (5)	0.0006 (5)	0.0018 (5)
C6	0.0200 (6)	0.0185 (6)	0.0167 (5)	−0.0002 (5)	−0.0023 (5)	0.0006 (5)
C7	0.0179 (6)	0.0208 (6)	0.0178 (6)	0.0018 (5)	−0.0025 (5)	−0.0009 (5)
C8	0.0116 (6)	0.0203 (6)	0.0178 (6)	−0.0004 (5)	−0.0014 (5)	−0.0005 (5)
C9	0.0152 (6)	0.0171 (6)	0.0155 (5)	−0.0002 (5)	0.0007 (5)	−0.0038 (5)
C10	0.0145 (6)	0.0248 (7)	0.0206 (6)	0.0027 (5)	−0.0050 (5)	0.0017 (5)
C11	0.0281 (8)	0.0429 (9)	0.0196 (6)	0.0005 (7)	−0.0040 (6)	0.0012 (6)
C12	0.0281 (8)	0.0264 (7)	0.0296 (7)	0.0064 (6)	−0.0033 (6)	0.0000 (6)
C13	0.0146 (7)	0.0421 (9)	0.0348 (8)	−0.0032 (6)	−0.0069 (6)	0.0052 (7)
C14	0.0364 (9)	0.0281 (7)	0.0232 (7)	−0.0031 (7)	0.0026 (6)	−0.0084 (6)
C15	0.0164 (6)	0.0189 (6)	0.0188 (6)	−0.0003 (5)	−0.0011 (5)	0.0037 (5)
N1	0.0129 (5)	0.0185 (5)	0.0196 (5)	−0.0023 (4)	−0.0008 (4)	0.0012 (4)
O1	0.0269 (5)	0.0215 (5)	0.0256 (5)	−0.0057 (4)	0.0063 (4)	−0.0059 (4)
O2	0.0191 (5)	0.0249 (5)	0.0224 (5)	−0.0012 (4)	0.0020 (4)	−0.0060 (4)
O3	0.0179 (5)	0.0250 (5)	0.0333 (5)	−0.0016 (4)	−0.0080 (4)	−0.0020 (4)
O4	0.0123 (4)	0.0210 (5)	0.0223 (4)	−0.0010 (3)	−0.0038 (4)	0.0031 (4)
O5	0.0175 (5)	0.0214 (5)	0.0221 (4)	−0.0027 (4)	0.0013 (4)	0.0028 (4)

Geometric parameters (Å, º) top

C1—C2	1.380 (2)	C10—O4	1.4834 (16)
C1—C6	1.3942 (19)	C10—C13	1.517 (2)
C1—H1A	0.9300	C10—C12	1.520 (2)
C2—C3	1.3997 (19)	C10—C11	1.524 (2)
C2—H2A	0.9300	C11—H11A	0.9600
C3—C4	1.3915 (19)	C11—H11B	0.9600
C3—C7	1.5079 (18)	C11—H11C	0.9600
C4—C5	1.391 (2)	C12—H12A	0.9600
C4—H4A	0.9300	C12—H12B	0.9600
C5—C6	1.3893 (19)	C12—H12C	0.9600
C5—H5A	0.9300	C13—H13A	0.9600
C6—O1	1.3653 (16)	C13—H13B	0.9600
C7—C8	1.5408 (19)	C13—H13C	0.9600
C7—H7A	0.9700	C14—O2	1.4578 (17)
C7—H7B	0.9700	C14—H14A	0.9600
C8—N1	1.4415 (16)	C14—H14B	0.9600
C8—C15	1.5265 (18)	C14—H14C	0.9600
C8—H8A	0.9800	C15—O3	1.2079 (18)
C9—O5	1.2210 (17)	C15—O2	1.3309 (17)
C9—O4	1.3424 (16)	N1—H1B	0.8600
C9—N1	1.3447 (17)	O1—H1C	0.8200

C2—C1—C6	119.69 (13)	O4—C10—C11	111.29 (12)
C2—C1—H1A	120.2	C13—C10—C11	110.79 (12)
C6—C1—H1A	120.2	C12—C10—C11	112.37 (13)
C1—C2—C3	121.55 (13)	C10—C11—H11A	109.5
C1—C2—H2A	119.2	C10—C11—H11B	109.5
C3—C2—H2A	119.2	H11A—C11—H11B	109.5
C4—C3—C2	117.90 (12)	C10—C11—H11C	109.5
C4—C3—C7	121.49 (12)	H11A—C11—H11C	109.5
C2—C3—C7	120.51 (12)	H11B—C11—H11C	109.5
C5—C4—C3	121.20 (12)	C10—C12—H12A	109.5
C5—C4—H4A	119.4	C10—C12—H12B	109.5
C3—C4—H4A	119.4	H12A—C12—H12B	109.5
C6—C5—C4	119.85 (12)	C10—C12—H12C	109.5
C6—C5—H5A	120.1	H12A—C12—H12C	109.5
C4—C5—H5A	120.1	H12B—C12—H12C	109.5
O1—C6—C5	122.90 (12)	C10—C13—H13A	109.5
O1—C6—C1	117.34 (12)	C10—C13—H13B	109.5
C5—C6—C1	119.75 (12)	H13A—C13—H13B	109.5
C3—C7—C8	114.62 (10)	C10—C13—H13C	109.5
C3—C7—H7A	108.6	H13A—C13—H13C	109.5
C8—C7—H7A	108.6	H13B—C13—H13C	109.5
C3—C7—H7B	108.6	O2—C14—H14A	109.5
C8—C7—H7B	108.6	O2—C14—H14B	109.5
H7A—C7—H7B	107.6	H14A—C14—H14B	109.5
N1—C8—C15	114.93 (11)	O2—C14—H14C	109.5
N1—C8—C7	109.87 (11)	H14A—C14—H14C	109.5
C15—C8—C7	107.10 (10)	H14B—C14—H14C	109.5
N1—C8—H8A	108.2	O3—C15—O2	123.75 (13)
C15—C8—H8A	108.2	O3—C15—C8	121.54 (12)
C7—C8—H8A	108.2	O2—C15—C8	114.67 (11)
O5—C9—O4	125.14 (13)	C9—N1—C8	121.70 (11)
O5—C9—N1	124.15 (13)	C9—N1—H1B	119.2
O4—C9—N1	110.71 (12)	C8—N1—H1B	119.2
O4—C10—C13	101.82 (11)	C6—O1—H1C	109.5
O4—C10—C12	109.26 (11)	C15—O2—C14	114.55 (12)
C13—C10—C12	110.83 (13)	C9—O4—C10	121.33 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O3ⁱ	0.86	2.27	3.0583 (16)	153
O1—H1C···O5ⁱⁱ	0.82	1.92	2.7356 (15)	180

Symmetry codes: (i) x+1/2, −y+3/2, −z; (ii) x, y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O3ⁱ	0.86	2.27	3.0583 (16)	153
O1—H1C···O5ⁱⁱ	0.82	1.92	2.7356 (15)	180

Symmetry codes: (i) x+1/2, −y+3/2, −z; (ii) x, y+1, z.

Acknowledgements

The author thanks Henan University of Traditional Chinese Medicine for supporting this study.

References

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