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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 3| March 2016| x160346
doi:10.1107/S2414314616003461

N-Hexyl-3,4-di­hy­droxy­benzamide

Tetsuji Moriguchi,a* Ryota Kamoto,a Venkataprasad Jallia and Akihiko Tsugea

aDepartment of Applied Chemistry, Graduate School of Engineering, Kyushu Institute of Technology, 1-1 Sensui-cho, Tobata-ku, Kitakyushu 804-8550, Japan
*Correspondence e-mail: moriguch@che.kyutech.ac.jp

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 8 February 2016; accepted 29 February 2016; online 4 March 2016)

In the title compound, C13H19NO3, the hexyl chain has en extended conformation and its mean plane is inclined to the benzene ring by 3.29 (10)°. There is a short O—H⋯O contact in the mol­ecule involving the adjacent hy­droxy groups. In the crystal, mol­ecules are linked via O—H⋯O and N—H⋯O hydrogen bonds, forming slabs parallel to (001). Within the slabs, there are also C—H⋯O hydrogen bonds and C—H⋯π inter­actions present.

CCDC reference: 1451378

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

N-alkyl-3,4-dihy­droxy benzamides are valuable in biological chemistry, having been identified as inhibitors of the trypanosome alternative oxidase in a cell-free mitochondrial preparation of Tiypanosoma brucei brucei (Grady et al., 1993[Grady, R. W., Bienen, E. J., Dieck, H. A., Saric, M. & Clarkson, A. B. (1993). Antimicrob. Agents Chemother. 37, 1082-1085.]). They were also used for the identification of potent anti­malarial agents against Plasmodium falciparum (3D7) parasites and a normal human cell line (Choomuenwai et al., 2013[Choomuenwai, V., Schwartz, B. D., Beattie, K. D., Andrews, K. T., Khokhar, S. & Davis, R. A. (2013). Tetrahedron Lett. 54, 5188-5191.]). Some 3,4-dihy­droxy benzamide derivatives have been used as inhibitors of ribonucleotide reductase with anti­neoplastic activity (Elford et al., 1979[Elford, H. L., Wampler, G. L. & van't Riet, B. (1979). Cancer Res. 39, 844-851.]).

The mol­ecular structure of the title compound is illustrated in Fig. 1[link]. The hexyl chain has en extended conformation and its mean plane [C8–C13; maximum deviation of 0.039 (2) Å for atom C12] is inclined to the benzene ring by 3.29 (10)°. The amide group (O3/C7/N1) is inclined to the benzene ring and the mean plane of the hexyl chain by 17.85 (14) and 16.33 (10)°, respectively. There is a short O—H⋯O contact in the mol­ecule involving adjacent hydroxy groups (Table 1[link]).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯O2 0.82 2.31 2.744 (2) 114
O1—H1⋯O2i 0.82 2.19 2.868 (2) 140
O2—H2⋯O3ii 0.82 1.96 2.754 (2) 162
N1—H7⋯O3iii 0.86 2.46 3.220 (2) 147
C3—H3⋯O3ii 0.93 2.53 3.155 (2) 125
C12—H12A⋯Cg1iv 0.97 2.92 3.763 (3) 146
Symmetry codes: (i) -x+3, -y+2, -z+2; (ii) -x+3, -y+1, -z+2; (iii) x-1, y, z; (iv) x-1, y-1, z+1.
[Figure 1]
Figure 1
The mol­ecular structure of the title compound, showing the atom labelling and displacement ellipsoids drawn at the 50% probability level.

In the crystal, mol­ecules are linked via O—H⋯O hydrogen bonds, forming ribbons along the b-axis direction which enclose R22(10) and R22(14) ring motifs (Table 1[link] and Fig. 2[link]). The ribbons are linked via N—H⋯O and C—H⋯O hydrogen bonds, forming slabs parallel to the ab plane (Table 1[link] and Figs. 3[link] and 4[link]). Within the slabs there are C—H⋯π inter­actions present (Table 1[link]).

[Figure 2]
Figure 2
Partial crystal packing diagram of the title compound, illustrating the formation of the hydrogen bonded (see Table 1[link]) ribbons extending in the b-axis direction.
[Figure 3]
Figure 3
Crystal packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines (see Table 1[link]) and H atoms not involved in these inter­actions have been omitted for clarity.
[Figure 4]
Figure 4
Crystal packing of the title compound, viewed along the c axis. Hydrogen bonds are shown as dashed lines (see Table 1[link]) and H atoms not involved in these inter­actions have been omitted for clarity.

Synthesis and crystallization

The synthesis of the title compound is illustrated in Fig. 5[link]. N-hexyl­amine (0.6 g, 5.5 mmol, 1.1 eq) and Et3N (0.6 g, 5.5 mmol, 1.1 eq) were added to 20 ml of freshly distilled CH2Cl2 and cooled to 273 K. To this mixture 3,4-dimeth­oxy benzoyl chloride (1 g, 5.0 mmol, 1 eq) in 10 ml CH2Cl2 was added dropwise. The mixture was stirred for 17 h at rt. The solvent was removed under reduced pressure. The resulting crude material was then dissolved in 40 ml of AcOEt. The organic phase was washed in 10% HCl, 10 ml of 10% Na2CO3, and brine solution. The organic layer was evaporated under reduced pressure and added to freshly distilled CH2Cl2 (10 ml). Under cooling, BBr3 (6 mmol) was added slowly to the solution. The mixture was stirred for 2 h at rt. After adding H2O (20 ml), the mixture was stirred for a few min, then the aqueous layer was extracted with Et2O. The organic phase was washed with brine, dried (Na2SO4), and concentrated under reduced pressure. The solid obtained was recrystallized in MeOH by slow evaporation at room temperature giving colourless prismatic crystals of the title compound.

[Figure 5]
Figure 5
Reaction scheme for the synthesis of the title compound.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C13H19NO3
Mr 237.29
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 120
a, b, c (Å) 5.2542 (17), 10.374 (3), 11.341 (4)
α, β, γ (°) 94.937 (3), 102.429 (3), 102.811 (3)
V (Å3) 582.8 (3)
Z 2
Radiation type Mo Kα
μ (mm−1) 0.10
Crystal size (mm) 0.45 × 0.30 × 0.25
 
Data collection
Diffractometer Bruker APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.766, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections 5584, 2055, 1735
Rint 0.026
(sin θ/λ)max (Å−1) 0.595
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.090, 1.04
No. of reflections 2055
No. of parameters 157
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.19, −0.20
Computer programs: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]), SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Structural data

CCDC reference: 1451378

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2414314616003461/su4015sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616003461/su4015Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616003461/su4015Isup3.cml

checkCIF report


Experimental top

The synthesis of the title compound is illustrated in Fig. 5. N-hexylamine (0.6 g, 5.5 mmol, 1.1 eq) and Et3N (0.6 g, 5.5 mmol, 1.1 eq) were added to 20 ml of freshly distilled CH2Cl2 and cooled to 273 K. To this mixture 3,4-dimethoxy benzoyl chloride (1 g, 5.0 mmol, 1 eq) in 10 ml CH2Cl2 was added dropwise. The mixture was stirred for 17 h at rt. The solvent was removed under reduced pressure. The resulting crude material was then dissolved in 40 ml of AcOEt. The organic phase was washed in 10% HCl, 10 ml of 10% Na2CO3, and brine solution. The organic layer was evaporated under reduced pressure and added to freshly distilled CH2Cl2 (10 ml). Under cooling, BBr3 (6 mmol) was added slowly to the solution. The mixture was stirred for 2 h at rt. After adding H2O (20 ml), the mixture was stirred for a few min, then the aqueous layer was extracted with Et2O. The organic phase was washed with brine, dried (Na2SO4), and concentrated under reduced pressure. The solid obtained was recrystallized in MeOH by slow evaporation at room temperature giving colourless prismatic crystals of the title compound.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2.

Structure description top

N-alkyl-3,4-dihydroxy benzamides are valuable in biological chemistry, having been identified as inhibitors of the trypanosome alternative oxidase in a cell-free mitochondrial preparation of Tiypanosoma brucei brucei (Grady et al., 1993). They were also used for the identification of potent antimalarial agents against Plasmodium falciparum (3D7) parasites and a normal human cell line (Choomuenwai et al., 2013). Some 3,4-dihydroxy benzamide derivatives have been used as inhibitors of ribonucleotide reductase with antineoplastic activity (Elford et al., 1979).

The molecular structure of the title compound is illustrated in Fig. 1. The hexyl chain has en extended conformation and its mean plane [C8–C13; maximum deviation of 0.039 (2) Å for atom C12] is inclined to the benzene ring by 3.29 (10)°. The amide group (O3/C7/N1) is inclined to the benzene ring and the mean plane of the hexyl chain by 17.85 (14) and 16.33 (10)°, respectively. There is a short O—H···O contact in the molecule involving adjacent hydroxyl groups (Table 1).

In the crystal, molecules are linked via O—H···O hydrogen bonds, forming ribbons along the b-axis direction which enclose R22(10) and R22(14) ring motifs (Table 1 and Fig. 2). The ribbons are linked via N—H···O and C—H···O hydrogen bonds, forming slabs parallel to the ab plane (Table 1 and Figs. 3 and 4). Within the slabs there are C—H···π interactions present (Table 1).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom labelling and displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Partial crystal packing diagram of the title compound, illustrating the formation of the hydrogen bonded (see Table 1) ribbons extending in the b-axis direction.
[Figure 3] Fig. 3. Crystal packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines (see Table 1) and H atoms not involved in these interactions have been omitted for clarity.
[Figure 4] Fig. 4. Crystal packing of the title compound, viewed along the c axis. Hydrogen bonds are shown as dashed lines (see Table 1) and H atoms not involved in these interactions have been omitted for clarity.
[Figure 5] Fig. 5. Reaction scheme for the synthesis of the title compound.
N-Hexyl-3,4-dihydroxybenzamide top
Crystal data top
C13H19NO3Z = 2
Mr = 237.29F(000) = 256
Triclinic, P1Dx = 1.352 Mg m−3
a = 5.2542 (17) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.374 (3) ÅCell parameters from 2404 reflections
c = 11.341 (4) Åθ = 2.6–25.0°
α = 94.937 (3)°µ = 0.10 mm−1
β = 102.429 (3)°T = 120 K
γ = 102.811 (3)°Prism, colourless
V = 582.8 (3) Å30.45 × 0.30 × 0.25 mm
Data collection top
Bruker APEXII CCD
diffractometer		2055 independent reflections
Radiation source: fine-focus sealed tube1735 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
Detector resolution: 16.6666 pixels mm-1θmax = 25.0°, θmin = 2.0°
ω scansh = −6→6
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		k = −12→12
Tmin = 0.766, Tmax = 0.976l = −13→13
5584 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0382P)2 + 0.1931P]
where P = (Fo2 + 2Fc2)/3
2055 reflections(Δ/σ)max < 0.001
157 parametersΔρmax = 0.19 e Å−3
0 restraintsΔρmin = −0.20 e Å−3
Crystal data top
C13H19NO3γ = 102.811 (3)°
Mr = 237.29V = 582.8 (3) Å3
Triclinic, P1Z = 2
a = 5.2542 (17) ÅMo Kα radiation
b = 10.374 (3) ŵ = 0.10 mm−1
c = 11.341 (4) ÅT = 120 K
α = 94.937 (3)°0.45 × 0.30 × 0.25 mm
β = 102.429 (3)°
Data collection top
Bruker APEXII CCD
diffractometer		2055 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		1735 reflections with I > 2σ(I)
Tmin = 0.766, Tmax = 0.976Rint = 0.026
5584 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.090H-atom parameters constrained
S = 1.04Δρmax = 0.19 e Å−3
2055 reflectionsΔρmin = −0.20 e Å−3
157 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
xyzUiso*/Ueq
C11.0844 (3)0.78967 (13)0.87939 (12)0.0183 (3)
C21.2999 (3)0.73975 (13)0.93220 (12)0.0175 (3)
C31.2798 (3)0.60507 (13)0.91268 (12)0.0179 (3)
H31.42640.57240.94630.021*
C41.0462 (3)0.51669 (13)0.84413 (11)0.0170 (3)
C50.8318 (3)0.56750 (13)0.79226 (12)0.0195 (3)
H50.67330.510.74570.023*
C60.8530 (3)0.70264 (14)0.80954 (13)0.0206 (3)
H60.70890.73580.77350.025*
C71.0362 (3)0.37214 (13)0.82975 (11)0.0169 (3)
C80.7592 (3)0.14432 (13)0.76710 (13)0.0195 (3)
H8A0.78090.10680.8430.023*
H8B0.8950.12570.72690.023*
C90.4842 (3)0.08023 (13)0.68689 (12)0.0191 (3)
H9A0.46370.11840.61130.023*
H9B0.34940.10010.72730.023*
C100.4357 (3)−0.06982 (13)0.65796 (13)0.0196 (3)
H10A0.5701−0.08920.61720.023*
H10B0.4588−0.10750.73380.023*
C110.1601 (3)−0.13682 (13)0.57857 (13)0.0206 (3)
H11A0.1334−0.09590.50460.025*
H11B0.0259−0.12120.62120.025*
C120.1159 (3)−0.28569 (13)0.54417 (13)0.0221 (3)
H12A0.1555−0.32590.61790.027*
H12B0.2407−0.30130.4960.027*
C13−0.1679 (3)−0.35323 (14)0.47253 (14)0.0276 (4)
H13A−0.2919−0.34250.52140.041*
H13B−0.1824−0.44660.45110.041*
H13C−0.2092−0.31340.39970.041*
N10.7959 (2)0.28767 (11)0.79265 (10)0.0191 (3)
H70.65570.31910.78330.023*
O11.0932 (2)0.92220 (9)0.89274 (9)0.0242 (3)
H11.23930.96380.93620.036*
O21.52394 (19)0.82996 (9)1.00208 (9)0.0213 (2)
H21.62320.79021.0420.032*
O31.24515 (18)0.33164 (9)0.85060 (8)0.0201 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0223 (8)0.0143 (7)0.0207 (7)0.0068 (6)0.0079 (6)0.0034 (5)
C20.0171 (7)0.0173 (7)0.0168 (7)0.0022 (6)0.0041 (6)0.0007 (5)
C30.0183 (7)0.0183 (7)0.0186 (7)0.0077 (6)0.0039 (6)0.0034 (5)
C40.0189 (7)0.0169 (7)0.0157 (7)0.0043 (6)0.0053 (6)0.0021 (5)
C50.0167 (7)0.0186 (7)0.0207 (7)0.0028 (6)0.0015 (6)0.0013 (5)
C60.0168 (7)0.0208 (7)0.0252 (7)0.0083 (6)0.0028 (6)0.0047 (6)
C70.0182 (7)0.0179 (7)0.0137 (6)0.0051 (6)0.0018 (5)0.0012 (5)
C80.0198 (7)0.0137 (7)0.0245 (7)0.0057 (6)0.0036 (6)0.0008 (5)
C90.0178 (7)0.0159 (7)0.0236 (7)0.0058 (6)0.0037 (6)0.0021 (6)
C100.0185 (8)0.0169 (7)0.0237 (7)0.0061 (6)0.0049 (6)0.0015 (6)
C110.0191 (7)0.0175 (7)0.0249 (7)0.0058 (6)0.0042 (6)0.0018 (6)
C120.0206 (8)0.0177 (7)0.0276 (8)0.0066 (6)0.0043 (6)0.0003 (6)
C130.0262 (8)0.0180 (7)0.0338 (8)0.0048 (6)0.0001 (7)−0.0016 (6)
N10.0157 (6)0.0147 (6)0.0257 (6)0.0054 (5)0.0021 (5)0.0006 (5)
O10.0226 (6)0.0140 (5)0.0326 (6)0.0055 (4)−0.0001 (5)0.0001 (4)
O20.0187 (5)0.0139 (5)0.0268 (5)0.0028 (4)−0.0020 (4)0.0001 (4)
O30.0174 (5)0.0164 (5)0.0243 (5)0.0053 (4)0.0002 (4)0.0004 (4)
Geometric parameters (Å, º) top
C1—O11.3596 (16)C9—C101.5152 (18)
C1—C61.3771 (19)C9—H9A0.97
C1—C21.389 (2)C9—H9B0.97
C2—O21.3683 (16)C10—C111.5087 (19)
C2—C31.3724 (19)C10—H10A0.97
C3—C41.3851 (19)C10—H10B0.97
C3—H30.93C11—C121.5131 (19)
C4—C51.3874 (19)C11—H11A0.97
C4—C71.4823 (19)C11—H11B0.97
C5—C61.375 (2)C12—C131.5136 (19)
C5—H50.93C12—H12A0.97
C6—H60.93C12—H12B0.97
C7—O31.2438 (16)C13—H13A0.96
C7—N11.3253 (17)C13—H13B0.96
C8—N11.4517 (17)C13—H13C0.96
C8—C91.5040 (19)N1—H70.86
C8—H8A0.97O1—H10.82
C8—H8B0.97O2—H20.82
O1—C1—C6118.18 (12)C10—C9—H9B109.1
O1—C1—C2122.54 (12)H9A—C9—H9B107.8
C6—C1—C2119.27 (12)C11—C10—C9113.60 (11)
O2—C2—C3123.39 (12)C11—C10—H10A108.8
O2—C2—C1117.08 (12)C9—C10—H10A108.8
C3—C2—C1119.53 (12)C11—C10—H10B108.8
C2—C3—C4121.52 (12)C9—C10—H10B108.8
C2—C3—H3119.2H10A—C10—H10B107.7
C4—C3—H3119.2C10—C11—C12113.76 (11)
C3—C4—C5118.47 (13)C10—C11—H11A108.8
C3—C4—C7118.58 (12)C12—C11—H11A108.8
C5—C4—C7122.95 (12)C10—C11—H11B108.8
C6—C5—C4120.18 (13)C12—C11—H11B108.8
C6—C5—H5119.9H11A—C11—H11B107.7
C4—C5—H5119.9C11—C12—C13113.17 (12)
C5—C6—C1121.00 (13)C11—C12—H12A108.9
C5—C6—H6119.5C13—C12—H12A108.9
C1—C6—H6119.5C11—C12—H12B108.9
O3—C7—N1121.25 (12)C13—C12—H12B108.9
O3—C7—C4121.37 (12)H12A—C12—H12B107.8
N1—C7—C4117.38 (12)C12—C13—H13A109.5
N1—C8—C9110.52 (11)C12—C13—H13B109.5
N1—C8—H8A109.5H13A—C13—H13B109.5
C9—C8—H8A109.5C12—C13—H13C109.5
N1—C8—H8B109.5H13A—C13—H13C109.5
C9—C8—H8B109.5H13B—C13—H13C109.5
H8A—C8—H8B108.1C7—N1—C8122.83 (11)
C8—C9—C10112.50 (11)C7—N1—H7118.6
C8—C9—H9A109.1C8—N1—H7118.6
C10—C9—H9A109.1C1—O1—H1109.5
C8—C9—H9B109.1C2—O2—H2109.5
O1—C1—C2—O21.6 (2)C2—C1—C6—C50.5 (2)
C6—C1—C2—O2−179.16 (12)C3—C4—C7—O3−17.92 (19)
O1—C1—C2—C3−178.48 (12)C5—C4—C7—O3162.25 (13)
C6—C1—C2—C30.8 (2)C3—C4—C7—N1162.71 (12)
O2—C2—C3—C4178.11 (12)C5—C4—C7—N1−17.1 (2)
C1—C2—C3—C4−1.9 (2)N1—C8—C9—C10−179.79 (11)
C2—C3—C4—C51.5 (2)C8—C9—C10—C11179.43 (12)
C2—C3—C4—C7−178.29 (12)C9—C10—C11—C12177.05 (12)
C3—C4—C5—C6−0.2 (2)C10—C11—C12—C13175.68 (12)
C7—C4—C5—C6179.63 (13)O3—C7—N1—C8−3.6 (2)
C4—C5—C6—C1−0.8 (2)C4—C7—N1—C8175.74 (11)
O1—C1—C6—C5179.83 (12)C9—C8—N1—C7−159.96 (12)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.822.312.744 (2)114
O1—H1···O2i0.822.192.868 (2)140
O2—H2···O3ii0.821.962.754 (2)162
N1—H7···O3iii0.862.463.220 (2)147
C3—H3···O3ii0.932.533.155 (2)125
C12—H12A···Cg1iv0.972.923.763 (3)146
Symmetry codes: (i) −x+3, −y+2, −z+2; (ii) −x+3, −y+1, −z+2; (iii) x−1, y, z; (iv) x−1, y−1, z+1.
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.822.312.744 (2)114
O1—H1···O2i0.822.192.868 (2)140
O2—H2···O3ii0.821.962.754 (2)162
N1—H7···O3iii0.862.463.220 (2)147
C3—H3···O3ii0.932.533.155 (2)125
C12—H12A···Cg1iv0.972.923.763 (3)146
Symmetry codes: (i) −x+3, −y+2, −z+2; (ii) −x+3, −y+1, −z+2; (iii) x−1, y, z; (iv) x−1, y−1, z+1.

Experimental details

Crystal data
Chemical formulaC13H19NO3
Mr237.29
Crystal system, space groupTriclinic, P1
Temperature (K)120
a, b, c (Å)5.2542 (17), 10.374 (3), 11.341 (4)
α, β, γ (°)94.937 (3), 102.429 (3), 102.811 (3)
V (Å3)582.8 (3)
Z2
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.45 × 0.30 × 0.25
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.766, 0.976
No. of measured, independent and
observed [I > 2σ(I)] reflections		5584, 2055, 1735
Rint0.026
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.090, 1.04
No. of reflections2055
No. of parameters157
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.19, −0.20

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

 

Acknowledgements

We are grateful to the Center for Instrumental Analysis, Kyushu Institute of Technology (KITCIA), for the X-ray analysis.

References

First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationChoomuenwai, V., Schwartz, B. D., Beattie, K. D., Andrews, K. T., Khokhar, S. & Davis, R. A. (2013). Tetrahedron Lett. 54, 5188–5191.  Web of Science CrossRef CAS Google Scholar
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 First citationMacrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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.

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 3| March 2016| x160346
doi:10.1107/S2414314616003461
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