2-Amino-4-(2-chloro-phen-yl)-5-oxo-5,6,7,8-tetra-hydro-4H-chromene-3-carbonitrile ethanol monosolvate.

In the title compound, C(16)H(13)ClN(2)O(2)·C(2)H(6)O, the fused cyclo-hexene 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 mol-ecules 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 inter-actions 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 = 346.80

Triclinic,

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[F 2 > 2σ(F 2)] = 0.082

wR(F 2) = 0.230

S = 0.90

3003 reflections

219 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.31 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811043650/bq2312sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811043650/bq2312Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H13ClN2O2·C2H6O	Z = 2
Mr = 346.80	F(000) = 364
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.126P)2] where P = (Fo2 + 2Fc2)/3
3003 reflections	(Δ/σ)max = 0.001
219 parameters	Δρmax = 0.36 e Å−3
1 restraint	Δρmin = −0.31 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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.

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) ; (ii) ; (iii) .