2-Amino-4-(2-chloro­phen­yl)-5-oxo-5,6,7,8-tetra­hydro-4H-chromene-3-carbonitrile ethanol monosolvate

Qiao, Y.; Kong, L.; Chen, G.; Li, S.; Gao, Z.

doi:10.1107/S1600536811043650

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3099

doi:10.1107/S1600536811043650

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2-Amino-4-(2-chlorophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile ethanol monosolvate

Yan Qiao,^a Lingqian Kong,^a,^b ^* Guifang Chen,^a Shengli Li ^a and Zhiqing Gao ^a

^aDongchang College, Liaocheng University, Liaocheng 250059, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: konglingqian08@163.com

(Received 11 October 2011; accepted 21 October 2011; online 29 October 2011)

In the title compound, C₁₆H₁₃ClN₂O₂·C₂H₆O, the fused cyclohexene and pyran rings adopt envelope and flattened boat conformations, respectively. In the crystal, N—H⋯O and O—H⋯O hydrogen bonds link the chromene and ethanol solvent molecules into infinite chains along the c axis, and N—H⋯N hydrogen bonds link these chains into a three-dimensional framework. Weak C—H⋯π interactions are also present.

Related literature

For the background, see: Lokaj et al. (1990 ); Marco et al. (1993 ). For crystal structures similar to the title compound, see: Tu et al. (2001 ).

Experimental

Crystal data

C₁₆H₁₃ClN₂O₂·C₂H₆O
M_r = 346.80
Triclinic, $[P \overline 1]$
a = 8.7610 (8) Å
b = 9.6281 (9) Å
c = 10.7951 (11) Å
α = 76.878 (1)°
β = 83.028 (2)°
γ = 77.632 (1)°
V = 863.69 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 298 K
0.47 × 0.46 × 0.21 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.896, T_max = 0.952
4606 measured reflections
3003 independent reflections
1428 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.082
wR(F²) = 0.230
S = 0.90
3003 reflections
219 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1ⁱ	0.86	2.19	3.037 (5)	167
N2—H2B⋯O3	0.86	1.99	2.851 (5)	178
O3—H3⋯O1ⁱⁱ	0.82	1.97	2.765 (5)	164
C14—H14B⋯Cgⁱⁱⁱ	0.97	2.96	3.704 (5)	135
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x, y, z+1; (iii) x-1, y, z.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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 I, global. DOI: 10.1107/S1600536811043650/bq2312sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811043650/bq2312Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811043650/bq2312Isup3.cml

checkCIF report

Comment top

The present investigation is a continuation of our work that includes syntheses and structural studies of polyfunctionalized substituted pyran derivatives, owing to their biological activities (Lokaj et al., 1990; Marco et al., 1993).We obtained the title compound, (I), and reported here its crystal structure in the paper.

In the crystal structure, it is observed that structure unit contains a substituted 5,6,7,8-tetrahydro-4H-chromene, a benzene ring and a ethanol solvate. The pyran ring adopts a sofa conformation, the dihedral angle between the (O2/C8-C11) plane and the C8/C7/C11 plane is 16.14 (4)°. Meanwhile, the (O2/C8-C11) plane forms an angle of 88.55 (13)° with the phenyl plane (C1-C6), which means that the pyran ring and the benzene ring is nearly perpendicular. In the crystal, the nitrile group is typical [N≡C = 1.148 (5)Å] and the carbonyl group also is reasonable [C═O =1.223 (6)Å].

Moreover, the plane (C10-C15) also adopts an chair configuration in the compound, and the dihedral angle between the (C10-C15) plane and the (C13-C15) plane is 46.19 (5)°.

In (I) (Fig. 1), the bond lengths and angles of the main molecule are normal and correspond to those observed in 2-amino-7,7-dimethyl-5-oxo-4-phenyl- 5,6,7,8-tetra-hydro-4H-chromene-3-carbonitrile (Tu et al., 2001).

In the crystal structure, there exist typical intermolecular N-H···N, N—H···O, O—H···O hydrogen bonds and weak C-H···π interactions (Table 1.). Intermolecular N-H···O and O—H···O hydrogen bonds link the molecules and ethanol solvent into infinite chain along c-axis and intermolecular hydrogen bonds link these chains forming three-dimensional framework.

Related literature top

For the background, see: Lokaj et al. (1990); Marco et al. (1993). For crystal structures similar to the title compound, see: Tu et al. (2001).

Experimental top

Malononitrile (5 mmol), 1,3-cyclohexanedione (5 mmol) and 2-chorobenzaldehyde (5 mmol) was dissolved in 20 ml DMF in a round-bottom flask. The mixture was warmed, with agitation, to 423 K over a period of 6 h. The resulting solution was cooled. Crystal of (I) suitable for X-ray diffraction analysis were obtained by recrystallized from ethanol.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 title molecule with the atomic numbering scheme. The displacement ellipsoids are shown at the 30% probability level.
	Fig. 2. The packing of the title compound. N-H···N, N-H···O and O-H···O interactions are represented with dashed lines.

2-Amino-4-(2-chlorophenyl)-5-oxo-5,6,7,8-tetrahydro- 4H-chromene-3-carbonitrile ethanol monosolvate top

Crystal data top

C₁₆H₁₃ClN₂O₂·C₂H₆O	Z = 2
M_r = 346.80	F(000) = 364
Triclinic, P1	D_x = 1.334 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7610 (8) Å	Cell parameters from 821 reflections
b = 9.6281 (9) Å	θ = 2.6–25.4°
c = 10.7951 (11) Å	µ = 0.24 mm⁻¹
α = 76.878 (1)°	T = 298 K
β = 83.028 (2)°	Block, red
γ = 77.632 (1)°	0.47 × 0.46 × 0.21 mm
V = 863.69 (14) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3003 independent reflections
Radiation source: fine-focus sealed tube	1428 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
phi and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.896, T_max = 0.952	k = −9→11
4606 measured reflections	l = −12→12

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)] = 0.082	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.230	H-atom parameters constrained
S = 0.90	w = 1/[σ²(F_o²) + (0.126P)²] where P = (F_o² + 2F_c²)/3
3003 reflections	(Δ/σ)_max = 0.001
219 parameters	Δρ_max = 0.36 e Å⁻³
1 restraint	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₆H₁₃ClN₂O₂·C₂H₆O	γ = 77.632 (1)°
M_r = 346.80	V = 863.69 (14) Å³
Triclinic, P1	Z = 2
a = 8.7610 (8) Å	Mo Kα radiation
b = 9.6281 (9) Å	µ = 0.24 mm⁻¹
c = 10.7951 (11) Å	T = 298 K
α = 76.878 (1)°	0.47 × 0.46 × 0.21 mm
β = 83.028 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3003 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1428 reflections with I > 2σ(I)
T_min = 0.896, T_max = 0.952	R_int = 0.057
4606 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.082	1 restraint
wR(F²) = 0.230	H-atom parameters constrained
S = 0.90	Δρ_max = 0.36 e Å⁻³
3003 reflections	Δρ_min = −0.31 e Å⁻³
219 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl1	0.94359 (18)	0.32844 (18)	0.01378 (14)	0.0853 (6)
N1	1.0042 (5)	0.4987 (5)	0.3508 (4)	0.0694 (13)
N2	0.7142 (4)	0.3876 (4)	0.6036 (4)	0.0543 (11)
H2A	0.7912	0.4295	0.6051	0.065*
H2B	0.6527	0.3694	0.6711	0.065*
O1	0.5581 (4)	0.2859 (5)	0.0845 (3)	0.0796 (12)
O2	0.5602 (3)	0.2879 (3)	0.5179 (3)	0.0531 (9)
O3	0.5099 (5)	0.3347 (6)	0.8285 (4)	0.1065 (16)
H3	0.5180	0.3377	0.9026	0.160*
C1	0.9531 (5)	0.1785 (6)	0.1361 (5)	0.0551 (13)
C2	1.0586 (6)	0.0538 (7)	0.1199 (6)	0.0659 (15)
H2	1.1212	0.0522	0.0441	0.079*
C3	1.0716 (6)	−0.0672 (7)	0.2153 (6)	0.0736 (16)
H3A	1.1434	−0.1508	0.2047	0.088*
C4	0.9784 (6)	−0.0667 (6)	0.3281 (6)	0.0707 (16)
H4	0.9861	−0.1494	0.3930	0.085*
C5	0.8745 (5)	0.0572 (5)	0.3432 (5)	0.0532 (12)
H5	0.8139	0.0577	0.4201	0.064*
C6	0.8560 (4)	0.1819 (5)	0.2487 (4)	0.0443 (11)
C7	0.7362 (4)	0.3145 (5)	0.2726 (4)	0.0429 (11)
H7	0.7373	0.3918	0.1960	0.051*
C8	0.7721 (5)	0.3698 (5)	0.3836 (4)	0.0437 (11)
C9	0.6906 (5)	0.3513 (5)	0.4982 (4)	0.0437 (11)
C10	0.5007 (5)	0.2644 (5)	0.4148 (4)	0.0454 (11)
C11	0.5740 (5)	0.2806 (5)	0.2992 (4)	0.0433 (11)
C12	0.4933 (5)	0.2721 (6)	0.1923 (5)	0.0561 (13)
C13	0.3260 (5)	0.2516 (7)	0.2181 (5)	0.0745 (17)
H13A	0.3012	0.2056	0.1539	0.089*
H13B	0.2570	0.3459	0.2115	0.089*
C14	0.2971 (6)	0.1595 (6)	0.3488 (5)	0.0670 (15)
H14A	0.3567	0.0616	0.3523	0.080*
H14B	0.1868	0.1544	0.3640	0.080*
C15	0.3445 (5)	0.2227 (5)	0.4516 (5)	0.0541 (13)
H15A	0.2668	0.3076	0.4644	0.065*
H15B	0.3487	0.1515	0.5313	0.065*
C16	0.8995 (5)	0.4412 (5)	0.3669 (4)	0.0489 (12)
C17	0.3742 (7)	0.2814 (7)	0.8216 (6)	0.097 (2)
H17A	0.3331	0.3234	0.7390	0.117*
H17B	0.2949	0.3108	0.8865	0.117*
C18	0.4070 (11)	0.1237 (8)	0.8401 (7)	0.136 (3)
H18A	0.4878	0.0942	0.7776	0.204*
H18B	0.3137	0.0910	0.8308	0.204*
H18C	0.4412	0.0817	0.9240	0.204*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0840 (11)	0.0960 (12)	0.0676 (10)	−0.0272 (9)	0.0204 (7)	−0.0043 (8)
N1	0.044 (2)	0.100 (4)	0.076 (3)	−0.036 (2)	0.001 (2)	−0.025 (3)
N2	0.046 (2)	0.078 (3)	0.050 (3)	−0.029 (2)	−0.0001 (18)	−0.021 (2)
O1	0.060 (2)	0.137 (4)	0.052 (2)	−0.040 (2)	−0.0035 (18)	−0.023 (2)
O2	0.0437 (17)	0.074 (2)	0.050 (2)	−0.0305 (16)	0.0028 (14)	−0.0154 (17)
O3	0.096 (3)	0.183 (5)	0.057 (3)	−0.070 (3)	0.008 (2)	−0.025 (3)
C1	0.041 (3)	0.071 (4)	0.062 (3)	−0.020 (3)	0.003 (2)	−0.026 (3)
C2	0.048 (3)	0.086 (4)	0.075 (4)	−0.018 (3)	0.009 (3)	−0.041 (4)
C3	0.050 (3)	0.074 (4)	0.101 (5)	−0.003 (3)	−0.005 (3)	−0.036 (4)
C4	0.058 (3)	0.069 (4)	0.084 (4)	−0.008 (3)	−0.010 (3)	−0.014 (3)
C5	0.037 (3)	0.061 (3)	0.061 (3)	−0.012 (2)	0.003 (2)	−0.014 (3)
C6	0.027 (2)	0.059 (3)	0.054 (3)	−0.018 (2)	0.0017 (19)	−0.018 (2)
C7	0.031 (2)	0.051 (3)	0.049 (3)	−0.016 (2)	0.0002 (18)	−0.008 (2)
C8	0.033 (2)	0.056 (3)	0.047 (3)	−0.017 (2)	−0.0002 (19)	−0.013 (2)
C9	0.031 (2)	0.050 (3)	0.053 (3)	−0.013 (2)	−0.0028 (19)	−0.012 (2)
C10	0.037 (2)	0.054 (3)	0.051 (3)	−0.017 (2)	−0.006 (2)	−0.015 (2)
C11	0.036 (2)	0.054 (3)	0.045 (3)	−0.015 (2)	0.000 (2)	−0.017 (2)
C12	0.045 (3)	0.074 (4)	0.057 (3)	−0.019 (2)	−0.004 (2)	−0.020 (3)
C13	0.038 (3)	0.125 (5)	0.074 (4)	−0.027 (3)	−0.010 (2)	−0.037 (4)
C14	0.043 (3)	0.091 (4)	0.079 (4)	−0.032 (3)	−0.001 (2)	−0.026 (3)
C15	0.036 (3)	0.068 (3)	0.062 (3)	−0.020 (2)	0.002 (2)	−0.015 (3)
C16	0.035 (2)	0.064 (3)	0.052 (3)	−0.014 (2)	−0.001 (2)	−0.018 (2)
C17	0.068 (4)	0.131 (7)	0.085 (5)	−0.004 (4)	0.002 (3)	−0.021 (4)
C18	0.203 (10)	0.088 (6)	0.102 (6)	−0.006 (6)	0.011 (6)	−0.020 (5)

Geometric parameters (Å, º) top

Cl1—C1	1.716 (5)	C6—CG	1.405 (4)
N1—C16	1.146 (5)	C6—C7	1.519 (6)
N2—C9	1.315 (5)	C7—C11	1.505 (5)
N2—H2A	0.8600	C7—C8	1.507 (6)
N2—H2B	0.8600	C7—H7	0.9800
O1—C12	1.223 (5)	C8—C9	1.346 (6)
O2—C10	1.367 (5)	C8—C16	1.405 (6)
O2—C9	1.379 (5)	C10—C11	1.324 (6)
O3—C17	1.407 (7)	C10—C15	1.491 (6)
O3—H3	0.8200	C11—C12	1.450 (6)
C1—CG	1.373 (5)	C12—C13	1.505 (6)
C1—C2	1.381 (7)	C13—C14	1.511 (7)
C1—C6	1.399 (6)	C13—H13A	0.9700
C2—C3	1.363 (7)	C13—H13B	0.9700
C2—CG	1.376 (5)	C14—C15	1.518 (6)
C2—H2	0.9300	C14—H14A	0.9700
C3—CG	1.376 (6)	C14—H14B	0.9700
C3—C4	1.382 (8)	C15—H15A	0.9700
C3—H3A	0.9300	C15—H15B	0.9700
C4—C5	1.366 (7)	C17—C18	1.455 (7)
C4—CG	1.380 (6)	C17—H17A	0.9700
C4—H4	0.9300	C17—H17B	0.9700
C5—CG	1.359 (5)	C18—H18A	0.9600
C5—C6	1.381 (6)	C18—H18B	0.9600
C5—H5	0.9300	C18—H18C	0.9600

C9—N2—H2A	120.0	C11—C10—C15	126.5 (4)
C9—N2—H2B	120.0	O2—C10—C15	110.5 (4)
H2A—N2—H2B	120.0	C10—C11—C12	119.2 (4)
C10—O2—C9	118.7 (3)	C10—C11—C7	122.6 (4)
C17—O3—H3	109.5	C12—C11—C7	118.1 (4)
CG—C1—C2	60.0 (3)	O1—C12—C11	120.8 (4)
CG—C1—C6	60.9 (3)	O1—C12—C13	121.4 (4)
C2—C1—C6	120.8 (5)	C11—C12—C13	117.7 (4)
CG—C1—Cl1	178.0 (4)	C12—C13—C14	112.0 (4)
C2—C1—Cl1	118.1 (4)	C12—C13—H13A	109.2
C6—C1—Cl1	121.1 (4)	C14—C13—H13A	109.2
C3—C2—CG	60.3 (3)	C12—C13—H13B	109.2
C3—C2—C1	120.0 (5)	C14—C13—H13B	109.2
CG—C2—C1	59.7 (3)	H13A—C13—H13B	107.9
C3—C2—H2	119.8	C13—C14—C15	110.9 (4)
CG—C2—H2	179.7	C13—C14—H14A	109.5
C1—C2—H2	120.1	C15—C14—H14A	109.5
C2—C3—CG	60.3 (3)	C13—C14—H14B	109.5
C2—C3—C4	120.4 (5)	C15—C14—H14B	109.5
CG—C3—C4	60.1 (3)	H14A—C14—H14B	108.1
C2—C3—H3A	120.0	C10—C15—C14	110.6 (4)
CG—C3—H3A	179.6	C10—C15—H15A	109.5
C4—C3—H3A	119.6	C14—C15—H15A	109.5
C5—C4—CG	59.3 (3)	C10—C15—H15B	109.5
C5—C4—C3	119.1 (6)	C14—C15—H15B	109.5
CG—C4—C3	59.7 (4)	H15A—C15—H15B	108.1
C5—C4—H4	120.3	N1—C16—C8	178.5 (5)
CG—C4—H4	179.5	O3—C17—C18	111.4 (6)
C3—C4—H4	120.6	O3—C17—H17A	109.3
CG—C5—C4	60.9 (3)	C18—C17—H17A	109.3
CG—C5—C6	61.7 (3)	O3—C17—H17B	109.3
C4—C5—C6	122.6 (5)	C18—C17—H17B	109.3
CG—C5—H5	179.0	H17A—C17—H17B	108.0
C4—C5—H5	118.7	C17—C18—H18A	109.5
C6—C5—H5	118.8	C17—C18—H18B	109.5
C5—C6—C1	117.0 (4)	H18A—C18—H18B	109.5
C5—C6—CG	58.4 (3)	C17—C18—H18C	109.5
C1—C6—CG	58.6 (3)	H18A—C18—H18C	109.5
C5—C6—C7	119.2 (4)	H18B—C18—H18C	109.5
C1—C6—C7	123.7 (4)	C5—CG—C1	120.4 (3)
CG—C6—C7	177.6 (4)	C5—CG—C3	120.0 (4)
C11—C7—C8	108.2 (3)	C1—CG—C3	119.7 (3)
C11—C7—C6	110.9 (3)	C5—CG—C2	179.3 (3)
C8—C7—C6	112.1 (3)	C1—CG—C2	60.3 (3)
C11—C7—H7	108.5	C3—CG—C2	59.4 (3)
C8—C7—H7	108.5	C5—CG—C4	59.8 (3)
C6—C7—H7	108.5	C1—CG—C4	179.8 (3)
C9—C8—C16	118.6 (4)	C3—CG—C4	60.2 (3)
C9—C8—C7	123.3 (4)	C2—CG—C4	119.5 (3)
C16—C8—C7	118.0 (4)	C5—CG—C6	59.9 (3)
N2—C9—C8	129.3 (4)	C1—CG—C6	60.5 (3)
N2—C9—O2	109.7 (4)	C3—CG—C6	179.6 (3)
C8—C9—O2	121.0 (4)	C2—CG—C6	120.8 (3)
C11—C10—O2	123.0 (4)	C4—CG—C6	119.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1ⁱ	0.86	2.19	3.037 (5)	167
N2—H2B···O3	0.86	1.99	2.851 (5)	178
O3—H3···O1ⁱⁱ	0.82	1.97	2.765 (5)	164
C14—H14B···CGⁱⁱⁱ	0.97	2.96	3.704 (5)	135

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃ClN₂O₂·C₂H₆O
M_r	346.80
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.7610 (8), 9.6281 (9), 10.7951 (11)
α, β, γ (°)	76.878 (1), 83.028 (2), 77.632 (1)
V (Å³)	863.69 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.47 × 0.46 × 0.21

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.896, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	4606, 3003, 1428
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.082, 0.230, 0.90
No. of reflections	3003
No. of parameters	219
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.31

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), 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
N2—H2A···N1ⁱ	0.86	2.19	3.037 (5)	167.2
N2—H2B···O3	0.86	1.99	2.851 (5)	177.9
O3—H3···O1ⁱⁱ	0.82	1.97	2.765 (5)	163.9
C14—H14B···CGⁱⁱⁱ	0.97	2.96	3.704 (5)	134.5

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

Acknowledgements

This project was supported by the Foundation of Dongchang College, Liaocheng University (grant No. LG0801).

References

Lokaj, J., Kettmann, V., Pavelčík, F., Ilavský, D. & Marchalín, Š. (1990). Acta Cryst. C46, 788–791. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Marco, J. L., Martin, G., Martin, N., Martinez-Grau, A., Seoane, C., Albert, A. & Cano, F. H. (1993). Tetrahedron, 49, 7133–7144. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Tu, S.-J., Deng, X., Fang, Y.-Y., Guo, Y.-M., Du, M. & Liu, X.-H. (2001). Acta Cryst. E57, o358–o359. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 11| November 2011| Page o3099

doi:10.1107/S1600536811043650

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

2-Amino-4-(2-chloro­phen­yl)-5-oxo-5,6,7,8-tetra­hydro-4H-chromene-3-carbo­nitrile ethanol monosolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-Amino-4-(2-chlorophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile ethanol monosolvate