4-Amino-2-methyl­quinoline monohydrate

Tai, X.-S.; Xu, J.; Feng, Y.-M.; Liang, Z.-P.

doi:10.1107/S1600536808013093

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1026

doi:10.1107/S1600536808013093

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4-Amino-2-methylquinoline monohydrate

Xi-Shi Tai,^a ^* Jun Xu,^b Yi-Min Feng ^a and Zu-Pei Liang ^a

^aDepartment of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China, and ^bWeifang Institute of Supervision and Inspection of Product Quality, Weifang 261031, People's Republic of China
^*Correspondence e-mail: taixishi@lzu.edu.cn

(Received 1 May 2008; accepted 3 May 2008; online 10 May 2008)

The crystal structure of the title compound, C₁₀H₁₀N₂·H₂O, is stabilized by intermolecular O—H⋯N, N—H⋯O and N—H⋯N hydrogen bonds.

Related literature

For related literature, see: Tai et al. (2003 , 2008 ); Tai, Yin & Feng (2007 ); Tai, Yin & Hao (2007 ); Tai, Yin et al. (2007 ); Tai & Feng (2008 ); Wang et al. (2007 ).

Experimental

Crystal data

C₁₀H₁₀N₂·H₂O
M_r = 176.22
Orthorhombic, P n a 2₁
a = 4.7432 (8) Å
b = 13.9070 (13) Å
c = 14.5129 (16) Å
V = 957.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 (2) K
0.43 × 0.35 × 0.32 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.966, T_max = 0.975
3925 measured reflections
882 independent reflections
716 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.093
S = 1.04
882 reflections
119 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.10 e Å⁻³
Δρ_min = −0.11 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1ⁱ	0.85	1.94	2.791 (3)	174
O1—H2⋯N1ⁱⁱ	0.85	1.96	2.805 (3)	171
N2—H2A⋯O1ⁱⁱⁱ	0.86	2.10	2.947 (4)	168
N2—H2B⋯N2^iv	0.86	2.51	3.321 (4)	158
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ ; (ii) x+1, y, z; (iii) $[-x+1, -y+1, z+{\script{1\over 2}}]$ ; (iv) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808013093/at2564sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808013093/at2564Isup2.hkl

checkCIF report

Comment top

As part of our ongoing studies of the coordination chemistry of ligands containing nitrogen (Tai et al., 2003; Tai, Yin & Feng, 2007; Tai, Yin, Feng & Kong, 2007; Tai, Yin & Hao, 2007; Tai & Feng, 2008; Tai, Feng & Zhang, 2008; Wang et al., 2007), we now report the structure of the title compound, (I), (Fig. 1).

In the molecule of (I), the geometrical parameters for (I) are normal. The packing is stabilized by the intermolecular O—H···N, N—H···O and N—H···N hydrogen bonds (Table 1).

Related literature top

For related literature, see: Tai et al. (2003); Tai et al. (2008); Tai, Yin & Feng (2007); Tai, Yin & Hao (2007); Tai, Yin et al. (2007); Tai & Feng (2008); Wang et al. (2007).

Experimental top

1 mmol of Ethyl benzoylacetate was added to a solution of 4-amino-2-methylquinoline (1 mmol) in 10 ml of 95% ethanol. The mixture was stirred for 2 h at refluxing temperature. Evaporating some ethanol, clear blocks of (I) were obtained after one weeks.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) showing 30% displacement ellipsoids.

4-Amino-2-methylquinoline monohydrate top

Crystal data top

C₁₀H₁₀N₂·H₂O	F(000) = 376
M_r = 176.22	D_x = 1.223 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1365 reflections
a = 4.7432 (8) Å	θ = 2.8–23.5°
b = 13.9070 (13) Å	µ = 0.08 mm⁻¹
c = 14.5129 (16) Å	T = 298 K
V = 957.3 (2) Å³	Block, colourless
Z = 4	0.43 × 0.35 × 0.32 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	882 independent reflections
Radiation source: fine-focus sealed tube	716 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −5→5
T_min = 0.966, T_max = 0.975	k = −16→15
3925 measured reflections	l = −14→17

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.093	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0498P)² + 0.1333P] where P = (F_o² + 2F_c²)/3
882 reflections	(Δ/σ)_max < 0.001
119 parameters	Δρ_max = 0.10 e Å⁻³
1 restraint	Δρ_min = −0.11 e Å⁻³

Crystal data top

C₁₀H₁₀N₂·H₂O	V = 957.3 (2) Å³
M_r = 176.22	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 4.7432 (8) Å	µ = 0.08 mm⁻¹
b = 13.9070 (13) Å	T = 298 K
c = 14.5129 (16) Å	0.43 × 0.35 × 0.32 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	882 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	716 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.975	R_int = 0.029
3925 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	1 restraint
wR(F²) = 0.093	H-atom parameters constrained
S = 1.05	Δρ_max = 0.10 e Å⁻³
882 reflections	Δρ_min = −0.11 e Å⁻³
119 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
N1	0.0728 (5)	0.56239 (17)	0.32460 (17)	0.0508 (7)
N2	0.2819 (6)	0.33360 (19)	0.49988 (18)	0.0612 (7)
H2A	0.1996	0.3288	0.5525	0.073*
H2B	0.4034	0.2911	0.4832	0.073*
O1	0.9245 (4)	0.69712 (15)	0.18915 (16)	0.0582 (6)
H1	1.0702	0.7326	0.1914	0.070*
H2	0.9510	0.6552	0.2309	0.070*
C1	−0.2458 (8)	0.6300 (2)	0.4362 (3)	0.0672 (9)
H1A	−0.2491	0.6802	0.3907	0.101*
H1B	−0.1891	0.6563	0.4945	0.101*
H1C	−0.4306	0.6024	0.4417	0.101*
C2	−0.0410 (6)	0.5538 (2)	0.4074 (2)	0.0488 (8)
C3	0.0273 (7)	0.4782 (2)	0.46651 (19)	0.0485 (7)
H3	−0.0600	0.4746	0.5238	0.058*
C4	0.2193 (6)	0.4091 (2)	0.44254 (18)	0.0452 (7)
C5	0.3470 (6)	0.4156 (2)	0.35341 (19)	0.0429 (7)
C6	0.5474 (7)	0.3508 (2)	0.3196 (2)	0.0523 (8)
H6	0.6030	0.2992	0.3562	0.063*
C7	0.6634 (8)	0.3615 (3)	0.2340 (2)	0.0608 (9)
H7	0.7952	0.3175	0.2124	0.073*
C8	0.5828 (7)	0.4388 (3)	0.1796 (3)	0.0631 (9)
H8	0.6624	0.4464	0.1215	0.076*
C9	0.3892 (7)	0.5037 (2)	0.20989 (19)	0.0568 (9)
H9	0.3382	0.5549	0.1722	0.068*
C10	0.2654 (6)	0.4944 (2)	0.29716 (19)	0.0455 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0487 (14)	0.0540 (14)	0.0498 (15)	−0.0009 (12)	−0.0061 (12)	0.0071 (12)
N2	0.0754 (19)	0.0656 (16)	0.0428 (14)	0.0058 (15)	0.0043 (13)	0.0133 (12)
O1	0.0614 (12)	0.0590 (11)	0.0544 (12)	−0.0011 (11)	−0.0117 (12)	0.0083 (10)
C1	0.062 (2)	0.066 (2)	0.074 (2)	0.0027 (18)	0.0037 (19)	−0.0011 (17)
C2	0.0423 (17)	0.0539 (17)	0.0502 (18)	−0.0078 (14)	−0.0049 (14)	−0.0016 (15)
C3	0.0465 (16)	0.0590 (18)	0.0401 (16)	−0.0100 (15)	0.0010 (13)	−0.0024 (14)
C4	0.0428 (17)	0.0520 (16)	0.0406 (15)	−0.0113 (14)	−0.0062 (13)	0.0053 (13)
C5	0.0404 (15)	0.0502 (16)	0.0381 (14)	−0.0100 (13)	−0.0040 (12)	0.0022 (11)
C6	0.0500 (17)	0.0549 (17)	0.0519 (18)	−0.0033 (14)	−0.0021 (15)	0.0059 (14)
C7	0.056 (2)	0.070 (2)	0.056 (2)	−0.0027 (16)	0.0065 (17)	−0.0026 (16)
C8	0.059 (2)	0.084 (2)	0.0464 (16)	−0.0094 (18)	0.0060 (17)	0.0093 (18)
C9	0.0569 (18)	0.069 (2)	0.0440 (19)	−0.0077 (18)	−0.0041 (14)	0.0147 (14)
C10	0.0416 (15)	0.0540 (17)	0.0408 (15)	−0.0100 (13)	−0.0067 (13)	0.0042 (13)

Geometric parameters (Å, º) top

N1—C2	1.322 (4)	C3—H3	0.9300
N1—C10	1.374 (4)	C4—C5	1.431 (4)
N2—C4	1.372 (4)	C5—C6	1.399 (4)
N2—H2A	0.8600	C5—C10	1.420 (4)
N2—H2B	0.8600	C6—C7	1.367 (5)
O1—H1	0.8500	C6—H6	0.9300
O1—H2	0.8499	C7—C8	1.387 (5)
C1—C2	1.497 (5)	C7—H7	0.9300
C1—H1A	0.9600	C8—C9	1.361 (5)
C1—H1B	0.9600	C8—H8	0.9300
C1—H1C	0.9600	C9—C10	1.402 (4)
C2—C3	1.396 (4)	C9—H9	0.9300
C3—C4	1.369 (4)

C2—N1—C10	118.2 (2)	N2—C4—C5	120.3 (3)
C4—N2—H2A	120.0	C6—C5—C10	118.7 (3)
C4—N2—H2B	120.0	C6—C5—C4	124.3 (3)
H2A—N2—H2B	120.0	C10—C5—C4	116.9 (3)
H1—O1—H2	104.5	C7—C6—C5	121.4 (3)
C2—C1—H1A	109.5	C7—C6—H6	119.3
C2—C1—H1B	109.5	C5—C6—H6	119.3
H1A—C1—H1B	109.5	C6—C7—C8	119.4 (3)
C2—C1—H1C	109.5	C6—C7—H7	120.3
H1A—C1—H1C	109.5	C8—C7—H7	120.3
H1B—C1—H1C	109.5	C9—C8—C7	121.1 (3)
N1—C2—C3	122.1 (3)	C9—C8—H8	119.4
N1—C2—C1	117.0 (3)	C7—C8—H8	119.4
C3—C2—C1	120.8 (3)	C8—C9—C10	120.8 (3)
C4—C3—C2	121.8 (3)	C8—C9—H9	119.6
C4—C3—H3	119.1	C10—C9—H9	119.6
C2—C3—H3	119.1	N1—C10—C9	118.4 (3)
C3—C4—N2	121.8 (3)	N1—C10—C5	123.1 (3)
C3—C4—C5	117.9 (3)	C9—C10—C5	118.5 (3)

C10—N1—C2—C3	−0.4 (4)	C5—C6—C7—C8	0.6 (5)
C10—N1—C2—C1	178.8 (3)	C6—C7—C8—C9	−0.4 (5)
N1—C2—C3—C4	0.9 (4)	C7—C8—C9—C10	0.1 (5)
C1—C2—C3—C4	−178.3 (3)	C2—N1—C10—C9	−179.3 (2)
C2—C3—C4—N2	−178.6 (3)	C2—N1—C10—C5	0.1 (4)
C2—C3—C4—C5	−1.0 (4)	C8—C9—C10—N1	179.5 (3)
C3—C4—C5—C6	179.6 (3)	C8—C9—C10—C5	0.1 (4)
N2—C4—C5—C6	−2.8 (4)	C6—C5—C10—N1	−179.2 (3)
C3—C4—C5—C10	0.7 (4)	C4—C5—C10—N1	−0.2 (4)
N2—C4—C5—C10	178.3 (2)	C6—C5—C10—C9	0.1 (4)
C10—C5—C6—C7	−0.5 (4)	C4—C5—C10—C9	179.1 (2)
C4—C5—C6—C7	−179.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1ⁱ	0.85	1.94	2.791 (3)	174
O1—H2···N1ⁱⁱ	0.85	1.96	2.805 (3)	171
N2—H2A···O1ⁱⁱⁱ	0.86	2.10	2.947 (4)	168
N2—H2B···N2^iv	0.86	2.51	3.321 (4)	158

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

Experimental details

Crystal data
Chemical formula	C₁₀H₁₀N₂·H₂O
M_r	176.22
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	298
a, b, c (Å)	4.7432 (8), 13.9070 (13), 14.5129 (16)
V (Å³)	957.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.43 × 0.35 × 0.32

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.966, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	3925, 882, 716
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.093, 1.05
No. of reflections	882
No. of parameters	119
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.10, −0.11

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1ⁱ	0.85	1.94	2.791 (3)	174
O1—H2···N1ⁱⁱ	0.85	1.96	2.805 (3)	171
N2—H2A···O1ⁱⁱⁱ	0.86	2.10	2.947 (4)	168
N2—H2B···N2^iv	0.86	2.51	3.321 (4)	158

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

Acknowledgements

The authors thank the National Natural Science Foundation of China (20671073), the Natural Science Foundation of Shandong (Y2007B60), the Science and Technology Foundation of Weifang and Weifang University for research grants.

References

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