4-Amino-2-methyl­quinoline monohydrate

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.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.033
• wR factor = 0.094
• Data-to-parameter ratio = 7.4

checkCIF/PLATON results

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Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.41
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.01
           From the CIF: _reflns_number_total                882
           Count of symmetry unique reflns          882
           Completeness (_total/calc)            100.00%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

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

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).

S2. Experimental

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.

S3. Refinement

The H atoms were placed geometrically (C—H = 0.93–0.96 Å, O—H = 0.852 Å, N—H = 0.86 Å) and refined as riding with U_iso(H) = 1.2 or 1.5U_eq(carrier).

Computing details

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

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

4-Amino-2-methylquinoline monohydrate

Crystal data

C10H10N2·H2O	F(000) = 376
Mr = 176.22	Dx = 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) Å^3	Block, colourless
Z = 4	0.43 × 0.35 × 0.32 mm

Data collection

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

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.093	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0498P)^2 + 0.1333P] where P = (Fo^2 + 2Fc^2)/3
882 reflections	(Δ/σ)max < 0.001
119 parameters	Δρmax = 0.10 e Å^−3
1 restraint	Δρmin = −0.11 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.

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

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

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)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1^i	0.85	1.94	2.791 (3)	174
O1—H2···N1^ii	0.85	1.96	2.805 (3)	171
N2—H2A···O1^iii	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.