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

Mohamed, S.K.; Akkurt, M.; Abdelhamid, A.A.; Singh, K.; Allahverdiyev, M.A.

doi:10.1107/S1600536812015838

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1414-o1415

doi:10.1107/S1600536812015838

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

Shaaban K. Mohamed,^a Mehmet Akkurt,^b ^* Antar A. Abdelhamid,^a Kuldip Singh ^c and M. A. Allahverdiyev ^d

^aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^cDepartment of Chemistry, University of Leicester, Leicester, England, and ^dDepartment of Organic Chemistry, Baku State University, Baku, Azerbaijan
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 4 April 2012; accepted 11 April 2012; online 18 April 2012)

In the title moleclue, C₁₆H₁₃ClN₂O₂, the cyclohexene ring is in a sofa conformation. The pyran ring is essentialy planar [maximum deviation = 0.038 (2) Å] and forms a dihedral angle of 89.68 (10)° with the benzene ring. In the crystal, molecules are linked by pairs of N—H⋯N hydrogen bonds, forming inversion dimers with R₂²(12) ring motifs. These dimers are further linked by N—H⋯O hydrogen bonds into chains along [110]. Weak C—H⋯O hydrogen bonds are also present.

Related literature

For pharmaceutical background to 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile derivatives, see: Gao et al. (2001 ); Xu et al. (2011 ); Luan et al. (2011 ); Wang & Zhu, (2007 ); O'Callaghan et al. (1995 ). For similar structures, see: Tu et al. (2001 ); Qiao et al. (2011 ); Kong et al. (2011 ); Hu et al. (2012 ). For standard bond lengths, see: Allen et al. (1987 ). For geometric analysis, see: Cremer & Pople (1975 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ); Etter et al. (1990 ).

Experimental

Crystal data

C₁₆H₁₃ClN₂O₂
M_r = 300.73
Monoclinic, C 2/c
a = 13.753 (4) Å
b = 11.077 (3) Å
c = 19.370 (6) Å
β = 107.856 (5)°
V = 2808.7 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 150 K
0.43 × 0.27 × 0.07 mm

Data collection

Bruker APEX 2000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.914, T_max = 0.981
10643 measured reflections
2755 independent reflections
2124 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.122
S = 1.02
2755 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N2ⁱ	0.88	2.25	3.132 (3)	177
N1—H1B⋯O1ⁱⁱ	0.88	2.15	2.955 (2)	151
C3—H3⋯N2ⁱⁱⁱ	0.95	2.48	3.226 (3)	135
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812015838/lh5452sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812015838/lh5452Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812015838/lh5452Isup3.cml

checkCIF report

Comment top

The existence of an amino group and cyano group in tetrahydrochromenone compounds make them great substrates for building up multi organic transformations (Luan et al., 2011), preparing poly-functionalized substituted pyran derivatives (Wang & Zhu, 2007) and designing of poly-heterocyclic compounds (O'Callaghan et al.,1995). Moreover, such derivatives of tetrahydrochromenones have attracted strong interests of pharmacists and biologists because of their potential application in the treatment of psoriatic arthritis and rheumatoid arthritis (Xu et al., 2011). They also have wide biological applications such as anti-anaphylaxis, anti-achondroplasty and anti-cancer activity (Gao et al., 2001). To continue to our interest in the synthesis of biologically active compounds we report herein the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The (C8–C13) cyclohexene ring is in a sofa conformation with puckering parameters (Cremer & Pople, 1975) of Q_T = 0.466 (3) Å, θ = 58.3 (2) ° and ϕ = 173.5 (3) °. The pyran ring (O2/C7/C8/C13—C15) is essentialy planar with a maximum deviation of 0.038 (2) Å for C7, and forms a dihedral angle of 89.68 (10)° with the benzene ring (C1-C6). The bond lengths (Allen et al., 1987) and angles are similar to those for reported structures (Tu et al., 2001; Qiao et al., 2011; Kong et al., 2011; Hu et al., 2012).

In the crystal, molecules are linked by pairs of intermolecular N—H···N hydrogen bonds, forming inversion dimers with R ₂ ²(12) ring motifs (Bernstein et al., 1995; Etter et al., 1990), and these dimers are connected by weak C—H···N and N—H···O hydrogen bonds, generating one-dimensional chains along [110] (Table 1, Fig. 2).

Related literature top

For pharmaceutical background to 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile derivatives, see: Gao et al. (2001); Xu et al. (2011); Luan et al. (2011); Wang & Zhu, (2007); O'Callaghan et al. (1995). For similar structures, see: Tu et al. (2001); Qiao et al. (2011); Kong et al. (2011); Hu et al. (2012). For standard bond lengths, see: Allen et al. (1987). For geometric analysis, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995); Etter et al. (1990).

Experimental top

The title compound (I) was formed during a three component reaction of an equimolar ratios of (4-chlorobenzylidene)propanedinitrile (1 mmol), (4-aminophenyl)methanol (1 mmol) and cyclohexane-1,3-dione (1 mmol). The reaction mixture was heated in ethanol at 351 K. The reaction was monitored with TLC until completed after 5 h, then left in fume cupboard at room temperature until solvent evaporated. The resulting solid mass was recrystallized from ethanol to afford good quality crystals suitable for X-ray diffraction. [Yield: 83%, m.p.: 513 K].

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. A view of the molecule of (I), with displacement ellipsoids for non-H atoms drawn at the 50% probability level.
	Fig. 2. Part of the crystal structure of (I) with hydrogen bonds shown as dashed lines. H atoms not involved in H-bonding are omitted for clarity. Symmetry codes: (b) -x+1, -y+1, -z+1; (c) x+1/2, y+1/2, z; (d) -x+1/2, -y+1/2, -z+1.

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

Crystal data top

C₁₆H₁₃ClN₂O₂	F(000) = 1248
M_r = 300.73	D_x = 1.422 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 833 reflections
a = 13.753 (4) Å	θ = 2.2–28.2°
b = 11.077 (3) Å	µ = 0.28 mm⁻¹
c = 19.370 (6) Å	T = 150 K
β = 107.856 (5)°	Plate, colourless
V = 2808.7 (14) Å³	0.43 × 0.27 × 0.07 mm
Z = 8

Data collection top

Bruker APEX 2000 CCD area-detector diffractometer	2755 independent reflections
Radiation source: fine-focus sealed tube	2124 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
phi and ω scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
T_min = 0.914, T_max = 0.981	k = −13→13
10643 measured reflections	l = −23→23

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0649P)²] where P = (F_o² + 2F_c²)/3
2755 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₆H₁₃ClN₂O₂	V = 2808.7 (14) Å³
M_r = 300.73	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 13.753 (4) Å	µ = 0.28 mm⁻¹
b = 11.077 (3) Å	T = 150 K
c = 19.370 (6) Å	0.43 × 0.27 × 0.07 mm
β = 107.856 (5)°

Data collection top

Bruker APEX 2000 CCD area-detector diffractometer	2755 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2124 reflections with I > 2σ(I)
T_min = 0.914, T_max = 0.981	R_int = 0.063
10643 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.02	Δρ_max = 0.35 e Å⁻³
2755 reflections	Δρ_min = −0.23 e Å⁻³
190 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.12556 (5)	0.07141 (5)	0.22343 (4)	0.0510 (2)
O1	−0.04515 (11)	0.45923 (13)	0.41373 (8)	0.0395 (5)
O2	0.20240 (10)	0.74455 (12)	0.39806 (8)	0.0320 (4)
N1	0.37218 (13)	0.72339 (15)	0.44001 (9)	0.0347 (6)
N2	0.41870 (14)	0.40760 (17)	0.49094 (11)	0.0440 (7)
C1	0.13012 (15)	0.19541 (19)	0.28039 (12)	0.0337 (7)
C2	0.12955 (16)	0.17534 (19)	0.35014 (13)	0.0374 (7)
C3	0.13788 (15)	0.27229 (18)	0.39614 (12)	0.0332 (7)
C4	0.14684 (14)	0.38895 (17)	0.37333 (11)	0.0274 (6)
C5	0.14494 (16)	0.40667 (18)	0.30168 (11)	0.0348 (7)
C6	0.13673 (16)	0.3107 (2)	0.25501 (12)	0.0378 (7)
C7	0.16120 (14)	0.49363 (17)	0.42613 (11)	0.0270 (6)
C8	0.08175 (14)	0.59034 (17)	0.40049 (10)	0.0274 (6)
C9	−0.02395 (15)	0.55980 (18)	0.39594 (11)	0.0311 (7)
C10	−0.10332 (17)	0.6565 (2)	0.37309 (14)	0.0470 (8)
C11	−0.07795 (17)	0.7496 (2)	0.32396 (14)	0.0465 (8)
C12	0.02871 (15)	0.80147 (18)	0.35920 (12)	0.0360 (7)
C13	0.10411 (15)	0.70407 (18)	0.38660 (11)	0.0286 (6)
C14	0.28249 (15)	0.66677 (18)	0.42763 (10)	0.0285 (6)
C15	0.26669 (14)	0.54985 (17)	0.44117 (11)	0.0271 (6)
C16	0.35154 (15)	0.47326 (19)	0.46903 (11)	0.0304 (7)
H1A	0.42960	0.68370	0.45910	0.0420*
H1B	0.37370	0.80030	0.42910	0.0420*
H2	0.12350	0.09570	0.36650	0.0450*
H3	0.13750	0.25880	0.44450	0.0400*
H5	0.14940	0.48630	0.28470	0.0420*
H6	0.13560	0.32360	0.20630	0.0450*
H7	0.15570	0.46120	0.47300	0.0320*
H10A	−0.11020	0.69730	0.41680	0.0560*
H10B	−0.16990	0.61890	0.34740	0.0560*
H11A	−0.12890	0.81560	0.31430	0.0560*
H11B	−0.08110	0.71180	0.27700	0.0560*
H12A	0.04920	0.85040	0.32320	0.0430*
H12B	0.02750	0.85500	0.39980	0.0430*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0542 (4)	0.0358 (4)	0.0625 (4)	0.0042 (3)	0.0171 (3)	−0.0181 (3)
O1	0.0357 (8)	0.0312 (9)	0.0545 (10)	−0.0086 (7)	0.0182 (7)	0.0011 (7)
O2	0.0301 (8)	0.0212 (7)	0.0432 (8)	−0.0032 (6)	0.0090 (6)	0.0040 (6)
N1	0.0288 (9)	0.0249 (9)	0.0471 (11)	−0.0069 (7)	0.0070 (8)	0.0050 (8)
N2	0.0314 (10)	0.0353 (11)	0.0633 (13)	−0.0011 (8)	0.0116 (9)	0.0139 (10)
C1	0.0238 (10)	0.0288 (12)	0.0460 (13)	0.0027 (9)	0.0071 (9)	−0.0091 (10)
C2	0.0363 (12)	0.0224 (11)	0.0545 (14)	−0.0011 (9)	0.0155 (10)	0.0015 (10)
C3	0.0345 (12)	0.0275 (11)	0.0383 (12)	−0.0036 (9)	0.0120 (9)	0.0030 (9)
C4	0.0224 (10)	0.0224 (10)	0.0366 (11)	−0.0036 (8)	0.0078 (8)	0.0000 (8)
C5	0.0405 (12)	0.0240 (11)	0.0390 (12)	−0.0003 (9)	0.0111 (10)	0.0028 (9)
C6	0.0410 (12)	0.0350 (13)	0.0359 (12)	0.0044 (10)	0.0095 (10)	−0.0001 (10)
C7	0.0279 (10)	0.0222 (10)	0.0309 (11)	−0.0038 (8)	0.0091 (8)	0.0027 (8)
C8	0.0268 (10)	0.0234 (11)	0.0319 (11)	−0.0009 (8)	0.0089 (8)	−0.0005 (8)
C9	0.0303 (11)	0.0285 (12)	0.0344 (11)	−0.0032 (9)	0.0099 (9)	−0.0045 (9)
C10	0.0290 (12)	0.0374 (13)	0.0759 (18)	0.0014 (10)	0.0182 (11)	0.0005 (12)
C11	0.0323 (13)	0.0334 (13)	0.0691 (17)	0.0046 (10)	0.0085 (12)	0.0082 (12)
C12	0.0365 (12)	0.0261 (11)	0.0441 (13)	0.0016 (9)	0.0104 (10)	0.0042 (10)
C13	0.0282 (11)	0.0261 (11)	0.0316 (11)	−0.0014 (9)	0.0095 (8)	−0.0025 (9)
C14	0.0278 (11)	0.0277 (11)	0.0287 (11)	−0.0018 (8)	0.0066 (8)	−0.0004 (8)
C15	0.0256 (10)	0.0230 (10)	0.0311 (11)	−0.0035 (8)	0.0064 (8)	0.0008 (8)
C16	0.0273 (11)	0.0262 (11)	0.0356 (12)	−0.0077 (9)	0.0067 (9)	0.0032 (9)

Geometric parameters (Å, º) top

Cl1—C1	1.751 (2)	C8—C13	1.343 (3)
O1—C9	1.227 (3)	C9—C10	1.496 (3)
O2—C13	1.376 (3)	C10—C11	1.515 (3)
O2—C14	1.377 (3)	C11—C12	1.528 (3)
N1—C14	1.338 (3)	C12—C13	1.478 (3)
N2—C16	1.150 (3)	C14—C15	1.352 (3)
N1—H1B	0.8800	C15—C16	1.410 (3)
N1—H1A	0.8800	C2—H2	0.9500
C1—C6	1.381 (3)	C3—H3	0.9500
C1—C2	1.372 (3)	C5—H5	0.9500
C2—C3	1.378 (3)	C6—H6	0.9500
C3—C4	1.383 (3)	C7—H7	1.0000
C4—C7	1.518 (3)	C10—H10A	0.9900
C4—C5	1.394 (3)	C10—H10B	0.9900
C5—C6	1.378 (3)	C11—H11A	0.9900
C7—C8	1.502 (3)	C11—H11B	0.9900
C7—C15	1.523 (3)	C12—H12A	0.9900
C8—C9	1.469 (3)	C12—H12B	0.9900

C13—O2—C14	118.95 (15)	O2—C14—C15	121.62 (19)
H1A—N1—H1B	120.00	C7—C15—C14	123.71 (18)
C14—N1—H1A	120.00	C7—C15—C16	117.10 (17)
C14—N1—H1B	120.00	C14—C15—C16	119.17 (19)
Cl1—C1—C2	118.92 (16)	N2—C16—C15	177.8 (2)
C2—C1—C6	121.4 (2)	C1—C2—H2	120.00
Cl1—C1—C6	119.64 (17)	C3—C2—H2	120.00
C1—C2—C3	119.1 (2)	C2—C3—H3	119.00
C2—C3—C4	121.3 (2)	C4—C3—H3	119.00
C3—C4—C7	120.28 (18)	C4—C5—H5	119.00
C3—C4—C5	118.24 (18)	C6—C5—H5	119.00
C5—C4—C7	121.46 (17)	C1—C6—H6	121.00
C4—C5—C6	121.16 (19)	C5—C6—H6	121.00
C1—C6—C5	118.8 (2)	C4—C7—H7	108.00
C8—C7—C15	109.00 (16)	C8—C7—H7	108.00
C4—C7—C8	113.00 (17)	C15—C7—H7	108.00
C4—C7—C15	111.14 (16)	C9—C10—H10A	109.00
C7—C8—C9	117.51 (17)	C9—C10—H10B	109.00
C7—C8—C13	123.17 (19)	C11—C10—H10A	109.00
C9—C8—C13	119.15 (18)	C11—C10—H10B	109.00
O1—C9—C8	120.54 (19)	H10A—C10—H10B	108.00
C8—C9—C10	118.15 (18)	C10—C11—H11A	110.00
O1—C9—C10	121.2 (2)	C10—C11—H11B	110.00
C9—C10—C11	112.7 (2)	C12—C11—H11A	109.00
C10—C11—C12	110.5 (2)	C12—C11—H11B	110.00
C11—C12—C13	110.97 (17)	H11A—C11—H11B	108.00
O2—C13—C8	123.17 (18)	C11—C12—H12A	109.00
O2—C13—C12	111.50 (17)	C11—C12—H12B	109.00
C8—C13—C12	125.3 (2)	C13—C12—H12A	109.00
N1—C14—C15	127.46 (19)	C13—C12—H12B	109.00
O2—C14—N1	110.92 (17)	H12A—C12—H12B	108.00

C13—O2—C14—N1	−175.33 (16)	C4—C7—C8—C13	−117.7 (2)
C13—O2—C14—C15	4.4 (3)	C15—C7—C8—C9	−168.89 (17)
C14—O2—C13—C8	−2.4 (3)	C15—C7—C8—C13	6.4 (3)
C14—O2—C13—C12	176.27 (17)	C8—C7—C15—C16	177.19 (17)
Cl1—C1—C2—C3	177.03 (18)	C13—C8—C9—C10	2.3 (3)
Cl1—C1—C6—C5	−177.07 (18)	C7—C8—C13—C12	178.03 (19)
C2—C1—C6—C5	1.3 (3)	C9—C8—C13—O2	171.79 (18)
C6—C1—C2—C3	−1.4 (3)	C7—C8—C13—O2	−3.5 (3)
C1—C2—C3—C4	−0.1 (3)	C7—C8—C9—O1	1.2 (3)
C2—C3—C4—C7	−177.0 (2)	C7—C8—C9—C10	177.81 (18)
C2—C3—C4—C5	1.4 (3)	C13—C8—C9—O1	−174.36 (19)
C3—C4—C7—C15	112.8 (2)	C9—C8—C13—C12	−6.7 (3)
C3—C4—C7—C8	−124.3 (2)	O1—C9—C10—C11	−154.9 (2)
C3—C4—C5—C6	−1.5 (3)	C8—C9—C10—C11	28.4 (3)
C5—C4—C7—C8	57.4 (3)	C9—C10—C11—C12	−53.7 (3)
C5—C4—C7—C15	−65.5 (2)	C10—C11—C12—C13	48.8 (2)
C7—C4—C5—C6	176.9 (2)	C11—C12—C13—O2	161.65 (18)
C4—C5—C6—C1	0.1 (3)	C11—C12—C13—C8	−19.7 (3)
C4—C7—C15—C14	120.7 (2)	O2—C14—C15—C7	−0.6 (3)
C4—C7—C15—C16	−57.6 (2)	O2—C14—C15—C16	177.71 (18)
C8—C7—C15—C14	−4.5 (3)	N1—C14—C15—C7	179.11 (19)
C4—C7—C8—C9	67.0 (2)	N1—C14—C15—C16	−2.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2ⁱ	0.88	2.25	3.132 (3)	177
N1—H1B···O1ⁱⁱ	0.88	2.15	2.955 (2)	151
C3—H3···N2ⁱⁱⁱ	0.95	2.48	3.226 (3)	135

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃ClN₂O₂
M_r	300.73
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	150
a, b, c (Å)	13.753 (4), 11.077 (3), 19.370 (6)
β (°)	107.856 (5)
V (Å³)	2808.7 (14)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.43 × 0.27 × 0.07

Data collection
Diffractometer	Bruker APEX 2000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.914, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	10643, 2755, 2124
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.122, 1.02
No. of reflections	2755
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.23

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2ⁱ	0.88	2.25	3.132 (3)	177
N1—H1B···O1ⁱⁱ	0.88	2.15	2.955 (2)	151
C3—H3···N2ⁱⁱⁱ	0.95	2.48	3.226 (3)	135

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

Acknowledgements

The authors gratefully thank the Higher Education Ministries in both the Arab Republic of Egypt and the Republic of Azerbaijan for their financial support to conduct this project. They also extend their thanks to Manchester Metropolitan University for facilitating this study.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Gao, Y., Tu, S.-J., Zhou, J.-F. & Shi, D.-Q. (2001). J. Org. Chem. 7, 535–537. Google Scholar
Hu, X.-L., Wang, Z.-X., Wang, F.-M. & Han, G.-F. (2012). Acta Cryst. E68, o823. CSD CrossRef IUCr Journals Google Scholar
Kong, L., Ju, X., Qiao, Y., Zhang, J. & Gao, Z. (2011). Acta Cryst. E67, o3100. Web of Science CSD CrossRef IUCr Journals Google Scholar
Luan, C.-J., Wang, J.-Q., Zhang, G.-H., Wang, W., Tang, S.-G. & Guo, C. (2011). J. Org. Chem. 31, 860–864. CAS Google Scholar
O'Callaghan, C. N., McMurry, T. B. H. & O'Brien, J. E. (1995). J. Chem. Soc. Perkin Trans. 1, pp. 417–420. Google Scholar
Qiao, Y., Kong, L., Chen, G., Li, S. & Gao, Z. (2011). Acta Cryst. E67, o3099. Web of Science CSD CrossRef IUCr Journals 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
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals 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
Wang, J. & Zhu, S.-L. (2007). Acta Cryst. E63, o4190. Web of Science CSD CrossRef IUCr Journals Google Scholar
Xu, J.-C., Li, W.-M., Zheng, H., Lai, Y.-F. & Zhang, P.-F. (2011). Tetrahedron, 67, 9582–9587. Web of Science CrossRef CAS Google Scholar

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Volume 68| Part 5| May 2012| Pages o1414-o1415

doi:10.1107/S1600536812015838

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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