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

Mohamed, S.K.; Akkurt, M.; Tahir, M.N.; Abdelhamid, A.A.; Albayati, M.R.

doi:10.1107/S1600536812024142

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages o1965-o1966

doi:10.1107/S1600536812024142

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

Shaaban K. Mohamed,^a Mehmet Akkurt,^b ^* Muhammad N. Tahir,^c Antar A. Abdelhamid ^a and Mustafa R. Albayati ^d

^aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^cUniversity of Sargodha, Department of Physics, Sargodha, Pakistan, and ^dKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 25 May 2012; accepted 26 May 2012; online 31 May 2012)

In the title compound, C₁₈H₁₇ClN₂O₂·C₃H₆O, the 4H-pyran ring is nearly planar [maximum deviation = −0.108 (1) Å] and the cyclohexene ring is puckered [puckering parameters Q_T = 0.4596 (17) Å, θ = 55.9 (2)° and φ = 226.5 (3)°]. The 4H-pyran ring is approximately perpendicular to the benzene ring [dihedral angle = 84.35 (7)°] and is almost coplanar with the mean plane of the cyclohexene ring [dihedral angle = 8.64 (7)°]. In the crystal, inversion-related main molecules are linked into dimers by pairs of N—H⋯N hydrogen bonds, generating an R₂²(12) graph-set motif. These dimers are further connected by N—H⋯O and C—H⋯N hydrogen bonds, forming a layer structure extending parallel to the (011) plane. In addition, the molecules within the layers interact with each other via C—H⋯π interactions.

Related literature

For the synthesis of chromene compounds, see: Coujon et al. (2002 ). For the bioactivity of chromene compounds see: Kaye & Nocanda (2002 ). For similar structures, see: Hu et al. (2012 ); Mohamed et al. (2012 ). For bond-length data, see: Allen et al. (1987 ). For puckering parameters, see: Cremer & Pople (1975 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₈H₁₇ClN₂O₂·C₃H₆O
M_r = 386.86
Triclinic, $[P \overline 1]$
a = 8.1707 (2) Å
b = 9.4386 (2) Å
c = 13.5192 (4) Å
α = 84.446 (1)°
β = 82.546 (2)°
γ = 78.625 (1)°
V = 1010.76 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 296 K
0.28 × 0.25 × 0.23 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.942, T_max = 0.952
16320 measured reflections
4769 independent reflections
3390 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.126
S = 1.04
4769 reflections
248 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the O1/C7–C11 and C1–C6 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1ⁱ	0.86	2.30	3.1552 (19)	171
N2—H2B⋯O2ⁱⁱ	0.86	2.15	2.9949 (18)	167
C2—H2⋯N1ⁱⁱⁱ	0.93	2.51	3.234 (2)	135
C17—H17A⋯Cg2^iv	0.96	2.93	3.8221 (18)	155
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x-1, y, z; (iii) -x+2, -y, -z+1; (iv) x, y+1, z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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/S1600536812024142/xu5550sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812024142/xu5550Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812024142/xu5550Isup3.cml

checkCIF report

Comment top

Chromene compounds are important group of oxygen heterocycles. They have employed as useful intermediate in the synthesis of a wide range of natural products (Coujon et al., 2002). Such compounds have exhibited anti-depressant, anti-hypertensive as well as anti-ischaemic properties (Kaye & Nocanda, 2002). This triggered us to extend our on-going research program in synthesis of bioactive molecules and their pharmaceutical applications towards the synthesis of chromene nucleus containing compounds. We report in this study the synthesis and crystal structure study of 2-amino-4-(4-chlorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile–propan-2-one (1:1).

In the title compound (I), (Fig. 1), the C10/C11/C13–C16 cyclohexene ring is puckered with the puckering parameters (Cremer & Pople, 1975) of Q_T = 0.4596 (17) Å, θ = 55.9 (2)° and ϕ = 226.5 (3)°. The O1/C7–C11 4H-pyran ring is nearly planar with a maximum deviation of -0.108 (1) Å for C7 and is approximately perpendicular to the C1–C6 benzene ring [dihedral angle = 84.35 (7)°] and is almost co-planar with the mean plane of the cyclohexene ring [dihedral angle = 8.64 (7) °]. Bond lengths (Allen et al., 1987) and angles of the title compound are within normal ranges and are comparable to similar structures (Hu et al., 2012; Mohamed et al., 2012).

In the crystal, a pair of intermolecular N—H···N hydrogen bonds link the main molecules into an inversion dimer, generating an R₂²(12) graph-set motif (Bernstein et al., 1995; Table 1, Fig. 2). The dimers are further connected by N—H···O and C—H···N hydrogen bonds, forming a layer of molecules parallel to (011) (Table 1, Fig. 2). The layers are interconnected by weak C—H···π interactions, producing a three-dimensional network.

Related literature top

For the synthesis of chromene compounds, see: Coujon et al. (2002). For the bioactivity of chromene compounds see: Kaye & Nocanda (2002). For similar structures, see: Hu et al. (2012); Mohamed et al. (2012). For bond-length data, see: Allen et al. (1987). For puckering parameters, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of 140 mg (1 mmol) 5,5-dimethylcyclohexane-1,3-dione, 140 mg (1 mmol) 4-chlorobenzaldehyde and 123 mg (4-aminophenyl)methanol in 50 ml ethanol was refluxed for 5 h. The excess solvent was removed under vacuum and the residual resin was washed with cold acetone. The solid that formed was filtered off, washed with cold ethanol, well drained then recrystallized from a mixture of ethanol–acetone (1:1). Crystals obtained were in good quality and suitable for X-ray diffraction (m.p. 461 K).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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. View of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
	Fig. 2. View of the dimers formed by pairs of N—H···N hydrogen bonds, with an R₂²(12) motif and the N—H···O and C—H···N hydrogen bonds which connect the dimers with each other. H atoms not involved in hydrogen bonds have been omitted for clarity.

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

Crystal data top

C₁₈H₁₇ClN₂O₂·C₃H₆O	Z = 2
M_r = 386.86	F(000) = 408
Triclinic, P1	D_x = 1.271 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1707 (2) Å	Cell parameters from 430 reflections
b = 9.4386 (2) Å	θ = 2.2–21°
c = 13.5192 (4) Å	µ = 0.21 mm⁻¹
α = 84.446 (1)°	T = 296 K
β = 82.546 (2)°	Prism, colourless
γ = 78.625 (1)°	0.28 × 0.25 × 0.23 mm
V = 1010.76 (4) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	4769 independent reflections
Radiation source: fine-focus sealed tube	3390 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 0.81 pixels mm^-1	θ_max = 27.9°, θ_min = 1.5°
ω scans	h = −9→10
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −12→12
T_min = 0.942, T_max = 0.952	l = −17→17
16320 measured reflections

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0552P)² + 0.2106P] where P = (F_o² + 2F_c²)/3
4769 reflections	(Δ/σ)_max < 0.001
248 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₈H₁₇ClN₂O₂·C₃H₆O	γ = 78.625 (1)°
M_r = 386.86	V = 1010.76 (4) Å³
Triclinic, P1	Z = 2
a = 8.1707 (2) Å	Mo Kα radiation
b = 9.4386 (2) Å	µ = 0.21 mm⁻¹
c = 13.5192 (4) Å	T = 296 K
α = 84.446 (1)°	0.28 × 0.25 × 0.23 mm
β = 82.546 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4769 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3390 reflections with I > 2σ(I)
T_min = 0.942, T_max = 0.952	R_int = 0.027
16320 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.04	Δρ_max = 0.33 e Å⁻³
4769 reflections	Δρ_min = −0.34 e Å⁻³
248 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	1.23217 (8)	−0.04097 (7)	0.07282 (5)	0.0908 (3)
O1	0.49042 (12)	0.48205 (10)	0.35120 (8)	0.0400 (3)
O2	1.05221 (14)	0.51811 (13)	0.37189 (11)	0.0565 (5)
N1	0.67987 (18)	0.01830 (15)	0.51140 (12)	0.0536 (5)
N2	0.36160 (16)	0.29958 (14)	0.40904 (11)	0.0480 (5)
C1	0.92881 (17)	0.24000 (15)	0.30888 (11)	0.0342 (4)
C2	1.05201 (19)	0.12327 (17)	0.33381 (14)	0.0460 (5)
C3	1.1449 (2)	0.03660 (19)	0.26177 (16)	0.0555 (6)
C4	1.1148 (2)	0.06724 (19)	0.16419 (15)	0.0531 (6)
C5	0.9934 (2)	0.18223 (19)	0.13653 (14)	0.0513 (6)
C6	0.9008 (2)	0.26753 (17)	0.20960 (12)	0.0430 (5)
C7	0.82134 (17)	0.32702 (15)	0.39096 (11)	0.0337 (4)
C8	0.65888 (18)	0.27155 (15)	0.42120 (11)	0.0335 (4)
C9	0.50856 (18)	0.34425 (15)	0.39607 (11)	0.0342 (4)
C10	0.62537 (18)	0.55179 (15)	0.33926 (11)	0.0334 (4)
C11	0.77873 (17)	0.48648 (15)	0.36014 (11)	0.0326 (4)
C12	0.66848 (18)	0.13136 (16)	0.47074 (12)	0.0380 (4)
C13	0.90997 (19)	0.57350 (16)	0.35344 (12)	0.0388 (5)
C14	0.8623 (2)	0.73361 (17)	0.32758 (14)	0.0463 (5)
C15	0.7272 (2)	0.77363 (16)	0.25591 (12)	0.0409 (5)
C16	0.57651 (18)	0.70488 (15)	0.30076 (12)	0.0387 (5)
C17	0.6697 (2)	0.93797 (18)	0.24419 (17)	0.0592 (7)
C18	0.7976 (2)	0.7186 (2)	0.15339 (14)	0.0564 (6)
O3	0.5451 (2)	0.50051 (18)	0.11608 (13)	0.0843 (7)
C19	0.4295 (3)	0.4388 (2)	0.11692 (15)	0.0603 (7)
C20	0.4577 (4)	0.2802 (3)	0.1159 (2)	0.0995 (13)
C21	0.2546 (3)	0.5175 (3)	0.1176 (3)	0.1166 (13)
H2	1.07260	0.10280	0.40020	0.0550*
H2A	0.35510	0.21450	0.43660	0.0580*
H2B	0.27340	0.35580	0.38990	0.0580*
H3	1.22690	−0.04170	0.27950	0.0670*
H5	0.97400	0.20230	0.06990	0.0620*
H6	0.81800	0.34500	0.19150	0.0520*
H7	0.88370	0.31470	0.44940	0.0410*
H14A	0.96180	0.76980	0.29740	0.0560*
H14B	0.82190	0.78160	0.38870	0.0560*
H16A	0.51530	0.76070	0.35500	0.0460*
H16B	0.50160	0.70960	0.25000	0.0460*
H17A	0.76440	0.98270	0.22010	0.0890*
H17B	0.62060	0.97280	0.30780	0.0890*
H17C	0.58780	0.96160	0.19740	0.0890*
H18A	0.71240	0.74390	0.10870	0.0850*
H18B	0.83210	0.61510	0.16000	0.0850*
H18C	0.89240	0.76210	0.12710	0.0850*
H20A	0.41990	0.25490	0.05680	0.1490*
H20B	0.39630	0.24090	0.17400	0.1490*
H20C	0.57550	0.24120	0.11620	0.1490*
H21A	0.25020	0.61800	0.12620	0.1750*
H21B	0.18550	0.47730	0.17170	0.1750*
H21C	0.21410	0.50840	0.05540	0.1750*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0881 (4)	0.0749 (4)	0.1017 (5)	−0.0010 (3)	0.0216 (3)	−0.0411 (3)
O1	0.0293 (5)	0.0326 (5)	0.0566 (7)	−0.0079 (4)	−0.0069 (5)	0.0111 (5)
O2	0.0351 (6)	0.0490 (7)	0.0871 (10)	−0.0102 (5)	−0.0169 (6)	0.0050 (6)
N1	0.0469 (8)	0.0429 (8)	0.0700 (10)	−0.0113 (6)	−0.0163 (7)	0.0197 (7)
N2	0.0314 (7)	0.0391 (7)	0.0715 (10)	−0.0099 (6)	−0.0074 (6)	0.0151 (7)
C1	0.0271 (7)	0.0287 (7)	0.0468 (9)	−0.0067 (6)	−0.0050 (6)	0.0019 (6)
C2	0.0354 (8)	0.0405 (9)	0.0591 (11)	−0.0009 (7)	−0.0090 (7)	0.0036 (8)
C3	0.0384 (9)	0.0392 (9)	0.0830 (14)	0.0046 (7)	−0.0040 (9)	−0.0041 (9)
C4	0.0451 (10)	0.0430 (9)	0.0698 (13)	−0.0097 (8)	0.0099 (8)	−0.0169 (8)
C5	0.0579 (11)	0.0464 (10)	0.0500 (10)	−0.0122 (8)	−0.0019 (8)	−0.0055 (8)
C6	0.0431 (9)	0.0350 (8)	0.0497 (10)	−0.0035 (7)	−0.0075 (7)	−0.0016 (7)
C7	0.0304 (7)	0.0318 (7)	0.0395 (8)	−0.0065 (6)	−0.0093 (6)	0.0036 (6)
C8	0.0330 (7)	0.0294 (7)	0.0371 (8)	−0.0063 (6)	−0.0038 (6)	0.0036 (6)
C9	0.0344 (7)	0.0308 (7)	0.0365 (8)	−0.0083 (6)	−0.0020 (6)	0.0037 (6)
C10	0.0323 (7)	0.0291 (7)	0.0384 (8)	−0.0078 (6)	−0.0012 (6)	−0.0006 (6)
C11	0.0306 (7)	0.0287 (7)	0.0383 (8)	−0.0060 (6)	−0.0031 (6)	−0.0011 (6)
C12	0.0315 (7)	0.0387 (8)	0.0430 (8)	−0.0066 (6)	−0.0072 (6)	0.0050 (7)
C13	0.0363 (8)	0.0367 (8)	0.0443 (9)	−0.0093 (6)	−0.0050 (6)	−0.0024 (6)
C14	0.0442 (9)	0.0355 (8)	0.0619 (11)	−0.0141 (7)	−0.0079 (8)	−0.0013 (7)
C15	0.0423 (8)	0.0298 (8)	0.0508 (9)	−0.0108 (6)	−0.0030 (7)	0.0019 (7)
C16	0.0360 (8)	0.0286 (7)	0.0488 (9)	−0.0032 (6)	−0.0022 (7)	0.0016 (6)
C17	0.0613 (11)	0.0318 (9)	0.0848 (14)	−0.0125 (8)	−0.0127 (10)	0.0085 (9)
C18	0.0596 (11)	0.0564 (11)	0.0512 (11)	−0.0167 (9)	0.0037 (8)	0.0048 (8)
O3	0.0928 (12)	0.0868 (11)	0.0863 (12)	−0.0419 (10)	−0.0209 (9)	−0.0046 (9)
C19	0.0682 (13)	0.0644 (12)	0.0506 (11)	−0.0211 (10)	−0.0033 (9)	−0.0024 (9)
C20	0.109 (2)	0.0637 (15)	0.132 (3)	−0.0259 (15)	−0.0305 (18)	0.0047 (15)
C21	0.0753 (18)	0.115 (2)	0.140 (3)	0.0068 (16)	0.0197 (17)	−0.006 (2)

Geometric parameters (Å, º) top

Cl1—C4	1.743 (2)	C15—C17	1.528 (2)
O1—C9	1.3697 (17)	C15—C18	1.529 (2)
O1—C10	1.3765 (18)	C2—H2	0.9300
O2—C13	1.223 (2)	C3—H3	0.9300
O3—C19	1.202 (3)	C5—H5	0.9300
N1—C12	1.145 (2)	C6—H6	0.9300
N2—C9	1.335 (2)	C7—H7	0.9800
N2—H2B	0.8600	C14—H14B	0.9700
N2—H2A	0.8600	C14—H14A	0.9700
C1—C2	1.385 (2)	C16—H16A	0.9700
C1—C6	1.382 (2)	C16—H16B	0.9700
C1—C7	1.522 (2)	C17—H17B	0.9600
C2—C3	1.383 (3)	C17—H17C	0.9600
C3—C4	1.366 (3)	C17—H17A	0.9600
C4—C5	1.377 (2)	C18—H18B	0.9600
C5—C6	1.384 (2)	C18—H18C	0.9600
C7—C11	1.507 (2)	C18—H18A	0.9600
C7—C8	1.515 (2)	C19—C20	1.470 (3)
C8—C9	1.351 (2)	C19—C21	1.474 (4)
C8—C12	1.417 (2)	C20—H20A	0.9600
C10—C11	1.335 (2)	C20—H20B	0.9600
C10—C16	1.483 (2)	C20—H20C	0.9600
C11—C13	1.463 (2)	C21—H21A	0.9600
C13—C14	1.503 (2)	C21—H21B	0.9600
C14—C15	1.530 (2)	C21—H21C	0.9600
C15—C16	1.533 (2)

C9—O1—C10	118.92 (11)	C4—C5—H5	121.00
C9—N2—H2B	120.00	C6—C5—H5	121.00
H2A—N2—H2B	120.00	C1—C6—H6	119.00
C9—N2—H2A	120.00	C5—C6—H6	119.00
C6—C1—C7	122.04 (13)	C1—C7—H7	108.00
C2—C1—C6	118.08 (14)	C8—C7—H7	108.00
C2—C1—C7	119.74 (14)	C11—C7—H7	108.00
C1—C2—C3	121.22 (17)	C13—C14—H14A	109.00
C2—C3—C4	119.25 (16)	C13—C14—H14B	109.00
Cl1—C4—C3	119.52 (14)	C15—C14—H14A	109.00
C3—C4—C5	121.21 (17)	C15—C14—H14B	109.00
Cl1—C4—C5	119.27 (15)	H14A—C14—H14B	108.00
C4—C5—C6	118.86 (17)	C10—C16—H16A	109.00
C1—C6—C5	121.37 (15)	C10—C16—H16B	109.00
C1—C7—C11	112.80 (12)	C15—C16—H16A	109.00
C1—C7—C8	110.40 (12)	C15—C16—H16B	109.00
C8—C7—C11	108.40 (12)	H16A—C16—H16B	108.00
C7—C8—C9	123.08 (13)	C15—C17—H17A	109.00
C7—C8—C12	117.87 (13)	C15—C17—H17B	109.00
C9—C8—C12	118.83 (14)	C15—C17—H17C	109.00
N2—C9—C8	128.24 (14)	H17A—C17—H17B	109.00
O1—C9—N2	110.31 (12)	H17A—C17—H17C	110.00
O1—C9—C8	121.45 (13)	H17B—C17—H17C	109.00
O1—C10—C11	122.99 (13)	C15—C18—H18A	109.00
O1—C10—C16	111.12 (12)	C15—C18—H18B	109.00
C11—C10—C16	125.89 (14)	C15—C18—H18C	109.00
C10—C11—C13	118.65 (13)	H18A—C18—H18B	109.00
C7—C11—C10	122.53 (13)	H18A—C18—H18C	109.00
C7—C11—C13	118.81 (12)	H18B—C18—H18C	110.00
N1—C12—C8	178.38 (17)	O3—C19—C20	120.9 (2)
O2—C13—C11	120.84 (14)	O3—C19—C21	122.05 (19)
O2—C13—C14	121.28 (14)	C20—C19—C21	117.0 (2)
C11—C13—C14	117.84 (13)	C19—C20—H20A	109.00
C13—C14—C15	113.74 (13)	C19—C20—H20B	110.00
C16—C15—C17	108.70 (13)	C19—C20—H20C	109.00
C16—C15—C18	110.90 (13)	H20A—C20—H20B	109.00
C17—C15—C18	108.98 (15)	H20A—C20—H20C	109.00
C14—C15—C18	109.79 (14)	H20B—C20—H20C	109.00
C14—C15—C16	108.05 (13)	C19—C21—H21A	109.00
C14—C15—C17	110.41 (13)	C19—C21—H21B	109.00
C10—C16—C15	113.11 (12)	C19—C21—H21C	109.00
C1—C2—H2	119.00	H21A—C21—H21B	109.00
C3—C2—H2	119.00	H21A—C21—H21C	110.00
C2—C3—H3	120.00	H21B—C21—H21C	109.00
C4—C3—H3	120.00

C9—O1—C10—C16	−173.19 (12)	C8—C7—C11—C10	−15.79 (19)
C10—O1—C9—N2	174.51 (12)	C8—C7—C11—C13	163.79 (13)
C10—O1—C9—C8	−5.5 (2)	C7—C8—C9—N2	172.17 (15)
C9—O1—C10—C11	7.0 (2)	C12—C8—C9—O1	177.72 (13)
C7—C1—C2—C3	176.02 (14)	C12—C8—C9—N2	−2.3 (2)
C2—C1—C6—C5	−0.5 (2)	C7—C8—C9—O1	−7.8 (2)
C7—C1—C6—C5	−176.29 (15)	O1—C10—C11—C7	5.0 (2)
C6—C1—C2—C3	0.1 (2)	O1—C10—C11—C13	−174.58 (13)
C2—C1—C7—C8	−94.69 (16)	C16—C10—C11—C7	−174.80 (14)
C2—C1—C7—C11	143.88 (14)	C16—C10—C11—C13	5.6 (2)
C6—C1—C7—C8	81.04 (17)	O1—C10—C16—C15	−162.22 (12)
C6—C1—C7—C11	−40.39 (19)	C11—C10—C16—C15	17.6 (2)
C1—C2—C3—C4	0.3 (3)	C7—C11—C13—O2	0.4 (2)
C2—C3—C4—Cl1	179.66 (13)	C7—C11—C13—C14	−176.99 (14)
C2—C3—C4—C5	−0.3 (3)	C10—C11—C13—O2	−180.00 (17)
Cl1—C4—C5—C6	180.00 (15)	C10—C11—C13—C14	2.6 (2)
C3—C4—C5—C6	−0.1 (3)	O2—C13—C14—C15	148.89 (16)
C4—C5—C6—C1	0.5 (3)	C11—C13—C14—C15	−33.7 (2)
C1—C7—C8—C12	67.77 (17)	C13—C14—C15—C16	53.89 (18)
C11—C7—C8—C9	17.28 (19)	C13—C14—C15—C17	172.65 (15)
C11—C7—C8—C12	−168.22 (13)	C13—C14—C15—C18	−67.18 (18)
C1—C7—C11—C10	106.77 (16)	C14—C15—C16—C10	−45.43 (17)
C1—C7—C8—C9	−106.73 (16)	C17—C15—C16—C10	−165.27 (14)
C1—C7—C11—C13	−73.65 (17)	C18—C15—C16—C10	74.94 (17)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the O1/C7–C11 and C1–C6 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1ⁱ	0.86	2.30	3.1552 (19)	171
N2—H2B···O2ⁱⁱ	0.86	2.15	2.9949 (18)	167
C2—H2···N1ⁱⁱⁱ	0.93	2.51	3.234 (2)	135
C6—H6···Cg1	0.93	2.76	3.0785 (17)	101
C17—H17A···Cg2^iv	0.96	2.93	3.8221 (18)	155

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇ClN₂O₂·C₃H₆O
M_r	386.86
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.1707 (2), 9.4386 (2), 13.5192 (4)
α, β, γ (°)	84.446 (1), 82.546 (2), 78.625 (1)
V (Å³)	1010.76 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.28 × 0.25 × 0.23

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.942, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	16320, 4769, 3390
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.126, 1.04
No. of reflections	4769
No. of parameters	248
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.34

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), 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

Cg1 and Cg2 are the centroids of the O1/C7–C11 and C1–C6 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1ⁱ	0.86	2.30	3.1552 (19)	171
N2—H2B···O2ⁱⁱ	0.86	2.15	2.9949 (18)	167
C2—H2···N1ⁱⁱⁱ	0.93	2.51	3.234 (2)	135
C17—H17A···Cg2^iv	0.96	2.93	3.8221 (18)	155

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

Acknowledgements

AAA is grateful to the Azerbaijan Academic Exchange programme for financial support of this study. We thank Manchester Metropolitan University, Erciyes University and the University of Sargodha for facilitating this work.

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). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Coujon, J. Y., Zammattio, F., Pagnoncelli, S., Boursereau, Y. & Kirschleger, B. (2002). Synlett, pp. 322–324. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science 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
Hu, X.-L., Wang, Z.-X., Wang, F.-M. & Han, G.-F. (2012). Acta Cryst. E68, o823. CSD CrossRef IUCr Journals Google Scholar
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Mohamed, S. K., Akkurt, M., Abdelhamid, A. A., Singh, K. & Allahverdiyev, M. A. (2012). Acta Cryst. E68, o1414–o1415. CSD CrossRef IUCr Journals Google Scholar
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Volume 68| Part 6| June 2012| Pages o1965-o1966

doi:10.1107/S1600536812024142

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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