2-Amino-4-(4-meth­oxy­phen­yl)-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.; Allahverdiyev, M.A.

doi:10.1107/S160053681202781X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Pages o2206-o2207

https://doi.org/10.1107/S160053681202781X

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2-Amino-4-(4-methoxyphenyl)-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 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, ^cUniversity of Sargodha, Department of Physics, Sargodha, Pakistan, and ^dDepartment of Organic Chemistry, Baku State University, Baku, Azerbaijan
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 18 June 2012; accepted 19 June 2012; online 27 June 2012)

In the crystal structure of the title compound, C₁₉H₂₀N₂O₃·C₃H₆O, molecules are linked into inversion dimers with an R₂²(12) motif by pairs of N—H⋯N hydrogen bonds. These dimers are further connected into chains running along the a axis by N—H⋯O hydrogen bonds. C—H⋯N and C—H⋯π interactions also feature in the packing. The cyclohexene ring adopts nearly an envelope conformation [puckering parameters are Q_T = 0.456 (2) Å, θ = 54.6 (3)° and φ = 225.2 (3)°].

Related literature

For pharmacological properties of 4H-chromene and fused 4H-chromene derivatives, see: Kemnitzer et al. (2007 , 2008 ); Abd-El-Aziz et al. (2004 , 2007 ); Sabry et al. (2011 ); Gourdeau et al. (2004 ); Mahdavi et al. (2011 ); Brühlmann et al. (2001 ). For a related structure, see: Mohamed et al. (2012 ). For puckering parameters, see: Cremer & Pople (1975 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₉H₂₀N₂O₃·C₃H₆O
M_r = 382.45
Triclinic, $[P \overline 1]$
a = 8.2037 (4) Å
b = 9.5319 (4) Å
c = 13.8390 (7) Å
α = 77.743 (2)°
β = 87.307 (3)°
γ = 80.672 (2)°
V = 1043.43 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.28 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.978, T_max = 0.983
16752 measured reflections
4917 independent reflections
3284 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.182
S = 1.04
4917 reflections
246 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the O2/C8–C10/C12/C13) 4H-pyran ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1ⁱ	0.86	2.30	3.142 (3)	168
N2—H2B⋯O3ⁱⁱ	0.86	2.19	3.029 (2)	165
C6—H6⋯N1ⁱⁱⁱ	0.93	2.51	3.258 (3)	137
C18—H18A⋯Cg2^iv	0.96	2.77	3.677 (2)	158
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x+1, y, z; (iii) -x+1, -y+1, -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: https://doi.org/10.1107/S160053681202781X/bt5943sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681202781X/bt5943Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681202781X/bt5943Isup3.cml

checkCIF report

Comment top

Compounds such as 4H-chromenes and fused 4H-chromenes are a great class of organic drugs due to their wide applications in chemo therapy. They exhibited anticancer activities (Kemnitzer et al., 2007, 2008; Abd-El-Aziz et al., 2004, 2007; Gourdeau et al., 2004; Sabry et al., 2011; Mahdavi et al., 2011) and have used in treatment of Alzheimer's disease and Schizophrenia disorder (Brühlmann et al., 2001). In this context and further to our on-going study in synthesis and biological investigation of 4H-chromene compounds (Mohamed et al. 2012), we report in this study the structure and synthesis of the title compound (I).

In the title compound (I) shown in Fig. 1, the C12–C17 cyclohexene and O2/C8—C10/C12/C13 4H-pyran rings are puckered with the puckering parameters (Cremer & Pople, 1975) of Q_T = 0.456 (2) ° A, θ = 54.6 (3) °, φ = 225.2 (3) °, and Q_T = 0.201 (2) Å, θ = 108.1 (5) °, φ = 354.7 (6) °, respectively. The bond lengths and bond angles in (I) are normal and are comparable with those of a related structure previously reported (Mohamed et al., 2012).

In the crystal structure, adjacent molecules are connected by the pairs of N—H···N hydrogen bonds, forming dimers, with an R²₂(12) motif (Bernstein et al., 1995; Table 1, Fig. 2). These dimers are further connected to chains running along the a axis by N—H···O hydrogen bonds. Furthermore, C—H···π interactions contribute to the stabilization of the crystal packing (Table 1, Fig. 2).

Related literature top

For pharmacological properties of 4H-chromene and fused 4H-chromene derivatives, see: Kemnitzer et al. (2007, 2008); Abd-El-Aziz et al. (2004, 2007); Sabry et al. (2011); Gourdeau et al. (2004); Mahdavi et al. (2011); Brühlmann et al. (2001). For a related structure, see: Mohamed et al. (2012). For puckering parameters, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

To a solution of 184 mg (1 mmol) (4-methoxybenzylidene)propanedinitrile in 50 ml ethanol, 140 mg (1 mmol) 5,5-dimethylcyclohexane-1,3-dione was added in presence of 123 mg (1 mmol) (4-aminophenyl)methanol as catalyst. The reaction mixture was refluxed at 350 K for 5 h, then cooled at ambient temperature. The resin product that formed was solidified by washing with acetone then filtered off under vacuum and recrystallized from ethanol. Single crystals suitable for X-ray diffraction were produced by slow evaporation of ethanol/acetone solution (1:1) of (I) over two days at room temperature. Yield is 86%, M.p. 443 K.

Structure description top

For pharmacological properties of 4H-chromene and fused 4H-chromene derivatives, see: Kemnitzer et al. (2007, 2008); Abd-El-Aziz et al. (2004, 2007); Sabry et al. (2011); Gourdeau et al. (2004); Mahdavi et al. (2011); Brühlmann et al. (2001). For a related structure, see: Mohamed et al. (2012). For puckering parameters, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

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. The molecular structure 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 connect the dimers with each other. H atoms not involved in hydrogen bonds have been omitted for clarity.

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

Crystal data top

C₁₉H₂₀N₂O₃·C₃H₆O	Z = 2
M_r = 382.45	F(000) = 408
Triclinic, P1	D_x = 1.217 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2037 (4) Å	Cell parameters from 360 reflections
b = 9.5319 (4) Å	θ = 21.3–3.4°
c = 13.8390 (7) Å	µ = 0.08 mm⁻¹
α = 77.743 (2)°	T = 296 K
β = 87.307 (3)°	Prism, white
γ = 80.672 (2)°	0.28 × 0.22 × 0.20 mm
V = 1043.43 (9) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	4917 independent reflections
Radiation source: fine-focus sealed tube	3284 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 0.81 pixels mm^-1	θ_max = 28.0°, θ_min = 2.2°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −12→9
T_min = 0.978, T_max = 0.983	l = −18→18
16752 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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.182	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0878P)² + 0.2431P] where P = (F_o² + 2F_c²)/3
4917 reflections	(Δ/σ)_max < 0.001
246 parameters	Δρ_max = 0.59 e Å⁻³
1 restraint	Δρ_min = −0.50 e Å⁻³

Crystal data top

C₁₉H₂₀N₂O₃·C₃H₆O	γ = 80.672 (2)°
M_r = 382.45	V = 1043.43 (9) Å³
Triclinic, P1	Z = 2
a = 8.2037 (4) Å	Mo Kα radiation
b = 9.5319 (4) Å	µ = 0.08 mm⁻¹
c = 13.8390 (7) Å	T = 296 K
α = 77.743 (2)°	0.28 × 0.22 × 0.20 mm
β = 87.307 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4917 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3284 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.983	R_int = 0.027
16752 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	1 restraint
wR(F²) = 0.182	H-atom parameters constrained
S = 1.04	Δρ_max = 0.59 e Å⁻³
4917 reflections	Δρ_min = −0.50 e Å⁻³
246 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
O1	0.4032 (2)	0.66247 (19)	0.08006 (13)	0.0802 (7)
O2	1.02042 (14)	0.08753 (13)	0.35411 (10)	0.0488 (4)
O3	0.45650 (17)	0.03885 (16)	0.37857 (13)	0.0629 (6)
N1	0.8196 (2)	0.4700 (2)	0.51973 (16)	0.0656 (7)
N2	1.14500 (19)	0.24295 (18)	0.41136 (14)	0.0563 (6)
C1	0.6070 (2)	0.33700 (18)	0.31182 (14)	0.0399 (5)
C2	0.6619 (2)	0.3463 (2)	0.21430 (15)	0.0483 (6)
C3	0.5919 (3)	0.4548 (2)	0.13983 (16)	0.0543 (7)
C4	0.4642 (3)	0.5588 (2)	0.16012 (16)	0.0532 (7)
C5	0.4076 (2)	0.5523 (2)	0.25594 (17)	0.0549 (7)
C6	0.4797 (2)	0.4416 (2)	0.33068 (15)	0.0473 (6)
C7	0.2741 (4)	0.7714 (3)	0.0945 (2)	0.0952 (11)
C8	0.6896 (2)	0.22102 (18)	0.39559 (14)	0.0389 (5)
C9	0.8474 (2)	0.26366 (19)	0.42629 (14)	0.0437 (4)
C10	0.9993 (2)	0.20384 (19)	0.39964 (14)	0.0419 (5)
C11	0.8333 (2)	0.37739 (19)	0.47771 (14)	0.0437 (4)
C12	0.8867 (2)	0.02105 (18)	0.34609 (14)	0.0408 (5)
C13	0.7325 (2)	0.07535 (18)	0.36796 (13)	0.0403 (5)
C14	0.5994 (2)	−0.00856 (19)	0.36226 (15)	0.0455 (6)
C15	0.6483 (2)	−0.1573 (2)	0.33914 (17)	0.0538 (7)
C16	0.7957 (3)	−0.1685 (2)	0.26744 (17)	0.0570 (5)
C17	0.9388 (2)	−0.11592 (19)	0.30923 (16)	0.0475 (6)
C18	0.8500 (3)	−0.3269 (2)	0.2591 (2)	0.0702 (9)
C19	0.7493 (3)	−0.0761 (2)	0.16615 (17)	0.0570 (5)
O4	0.0402 (4)	0.1650 (4)	0.0951 (3)	0.1652 (16)
C20	0.1432 (4)	0.2327 (4)	0.1086 (2)	0.0875 (11)
C21	0.3163 (5)	0.1707 (5)	0.1206 (4)	0.149 (2)
C22	0.1030 (5)	0.3830 (4)	0.1273 (4)	0.142 (2)
H2	0.74790	0.27740	0.19950	0.0580*
H2A	1.14960	0.31490	0.43900	0.0680*
H2B	1.23420	0.19620	0.39120	0.0680*
H3	0.63040	0.45860	0.07520	0.0650*
H5	0.32180	0.62150	0.27050	0.0660*
H6	0.44110	0.43780	0.39530	0.0570*
H7A	0.18230	0.72780	0.12580	0.1420*
H7B	0.24060	0.83210	0.03180	0.1420*
H7C	0.31060	0.82910	0.13580	0.1420*
H8	0.61350	0.21200	0.45250	0.0470*
H15A	0.55440	−0.18350	0.31090	0.0650*
H15B	0.67530	−0.22710	0.40040	0.0650*
H17A	0.98780	−0.19130	0.36310	0.0570*
H17B	1.02270	−0.10000	0.25810	0.0570*
H18A	0.75920	−0.36330	0.23680	0.1050*
H18B	0.88460	−0.38430	0.32260	0.1050*
H18C	0.94030	−0.33260	0.21270	0.1050*
H19A	0.71430	0.02300	0.17170	0.0850*
H19B	0.66090	−0.11140	0.14030	0.0850*
H19C	0.84340	−0.08150	0.12240	0.0850*
H21A	0.35150	0.17590	0.18470	0.2240*
H21B	0.38070	0.22410	0.07060	0.2240*
H21C	0.33130	0.07090	0.11440	0.2240*
H22A	0.15880	0.44750	0.07910	0.2140*
H22B	0.13850	0.38360	0.19230	0.2140*
H22C	−0.01410	0.41450	0.12260	0.2140*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0853 (12)	0.0744 (11)	0.0695 (11)	0.0109 (9)	−0.0079 (9)	−0.0055 (9)
O2	0.0325 (6)	0.0517 (7)	0.0730 (9)	−0.0094 (5)	0.0028 (6)	−0.0355 (7)
O3	0.0363 (7)	0.0646 (9)	0.0955 (12)	−0.0134 (6)	0.0069 (7)	−0.0313 (8)
N1	0.0476 (10)	0.0739 (12)	0.0915 (14)	−0.0128 (9)	0.0111 (9)	−0.0534 (11)
N2	0.0338 (8)	0.0609 (10)	0.0875 (13)	−0.0101 (7)	−0.0002 (8)	−0.0433 (9)
C1	0.0310 (8)	0.0410 (9)	0.0535 (11)	−0.0093 (7)	0.0008 (7)	−0.0203 (8)
C2	0.0443 (10)	0.0474 (10)	0.0576 (12)	−0.0066 (8)	0.0043 (9)	−0.0224 (9)
C3	0.0581 (12)	0.0571 (11)	0.0512 (12)	−0.0099 (10)	0.0041 (10)	−0.0193 (9)
C4	0.0499 (11)	0.0530 (11)	0.0580 (13)	−0.0082 (9)	−0.0084 (10)	−0.0128 (9)
C5	0.0408 (10)	0.0538 (11)	0.0708 (14)	0.0020 (8)	−0.0011 (9)	−0.0216 (10)
C6	0.0367 (9)	0.0521 (10)	0.0557 (12)	−0.0056 (8)	0.0043 (8)	−0.0189 (9)
C7	0.093 (2)	0.0738 (17)	0.101 (2)	0.0192 (15)	−0.0154 (17)	−0.0002 (15)
C8	0.0314 (8)	0.0416 (9)	0.0480 (10)	−0.0077 (7)	0.0039 (7)	−0.0184 (7)
C9	0.0351 (7)	0.0473 (7)	0.0538 (8)	−0.0064 (5)	0.0003 (6)	−0.0222 (6)
C10	0.0381 (9)	0.0428 (9)	0.0505 (10)	−0.0070 (7)	−0.0030 (8)	−0.0214 (8)
C11	0.0351 (7)	0.0473 (7)	0.0538 (8)	−0.0064 (5)	0.0003 (6)	−0.0222 (6)
C12	0.0355 (9)	0.0407 (9)	0.0504 (10)	−0.0082 (7)	−0.0015 (8)	−0.0172 (8)
C13	0.0350 (9)	0.0401 (9)	0.0484 (10)	−0.0073 (7)	−0.0005 (7)	−0.0142 (7)
C14	0.0388 (10)	0.0458 (9)	0.0553 (11)	−0.0118 (8)	0.0007 (8)	−0.0145 (8)
C15	0.0479 (11)	0.0469 (10)	0.0738 (14)	−0.0187 (8)	0.0022 (10)	−0.0208 (9)
C16	0.0577 (9)	0.0558 (8)	0.0649 (9)	−0.0136 (7)	−0.0035 (7)	−0.0248 (7)
C17	0.0408 (10)	0.0410 (9)	0.0656 (13)	−0.0045 (7)	−0.0014 (9)	−0.0233 (9)
C18	0.0664 (14)	0.0530 (12)	0.1049 (19)	−0.0192 (10)	0.0059 (13)	−0.0410 (13)
C19	0.0577 (9)	0.0558 (8)	0.0649 (9)	−0.0136 (7)	−0.0035 (7)	−0.0248 (7)
O4	0.118 (2)	0.219 (3)	0.206 (3)	−0.089 (2)	0.007 (2)	−0.104 (3)
C20	0.0769 (19)	0.110 (2)	0.090 (2)	−0.0446 (17)	0.0029 (15)	−0.0312 (17)
C21	0.092 (3)	0.125 (3)	0.237 (6)	−0.014 (2)	−0.018 (3)	−0.049 (4)
C22	0.115 (3)	0.115 (3)	0.199 (5)	−0.032 (2)	0.019 (3)	−0.031 (3)

Geometric parameters (Å, º) top

O1—C4	1.372 (3)	C16—C18	1.531 (3)
O1—C7	1.397 (4)	C2—H2	0.9300
O2—C10	1.371 (2)	C3—H3	0.9300
O2—C12	1.373 (2)	C5—H5	0.9300
O3—C14	1.215 (2)	C6—H6	0.9300
O4—C20	1.187 (5)	C7—H7B	0.9600
N1—C11	1.144 (3)	C7—H7C	0.9600
N2—C10	1.335 (2)	C7—H7A	0.9600
N2—H2B	0.8600	C8—H8	0.9800
N2—H2A	0.8600	C15—H15B	0.9700
C1—C2	1.392 (3)	C15—H15A	0.9700
C1—C8	1.521 (3)	C17—H17A	0.9700
C1—C6	1.379 (3)	C17—H17B	0.9700
C2—C3	1.368 (3)	C18—H18B	0.9600
C3—C4	1.383 (3)	C18—H18C	0.9600
C4—C5	1.376 (3)	C18—H18A	0.9600
C5—C6	1.387 (3)	C19—H19B	0.9600
C8—C9	1.522 (2)	C19—H19C	0.9600
C8—C13	1.501 (2)	C19—H19A	0.9600
C9—C10	1.353 (2)	C20—C21	1.450 (5)
C9—C11	1.405 (3)	C20—C22	1.492 (5)
C12—C13	1.333 (2)	C21—H21A	0.9600
C12—C17	1.493 (3)	C21—H21B	0.9600
C13—C14	1.468 (2)	C21—H21C	0.9600
C14—C15	1.507 (3)	C22—H22A	0.9600
C15—C16	1.533 (3)	C22—H22B	0.9600
C16—C19	1.518 (3)	C22—H22C	0.9600
C16—C17	1.530 (3)

C4—O1—C7	119.00 (19)	C1—C6—H6	119.00
C10—O2—C12	118.71 (13)	C5—C6—H6	119.00
C10—N2—H2B	120.00	O1—C7—H7A	109.00
H2A—N2—H2B	120.00	O1—C7—H7B	109.00
C10—N2—H2A	120.00	O1—C7—H7C	110.00
C6—C1—C8	120.86 (17)	H7A—C7—H7B	109.00
C2—C1—C6	117.49 (17)	H7A—C7—H7C	110.00
C2—C1—C8	121.58 (16)	H7B—C7—H7C	109.00
C1—C2—C3	121.33 (18)	C1—C8—H8	108.00
C2—C3—C4	120.4 (2)	C9—C8—H8	108.00
O1—C4—C3	115.55 (19)	C13—C8—H8	109.00
C3—C4—C5	119.50 (19)	C14—C15—H15A	109.00
O1—C4—C5	124.96 (19)	C14—C15—H15B	109.00
C4—C5—C6	119.47 (18)	C16—C15—H15A	109.00
C1—C6—C5	121.83 (18)	C16—C15—H15B	109.00
C1—C8—C13	112.40 (15)	H15A—C15—H15B	108.00
C1—C8—C9	110.68 (14)	C12—C17—H17A	109.00
C9—C8—C13	108.21 (14)	C12—C17—H17B	109.00
C8—C9—C10	122.50 (16)	C16—C17—H17A	109.00
C8—C9—C11	118.28 (15)	C16—C17—H17B	109.00
C10—C9—C11	119.04 (16)	H17A—C17—H17B	108.00
N2—C10—C9	128.41 (18)	C16—C18—H18A	109.00
O2—C10—N2	110.29 (15)	C16—C18—H18B	110.00
O2—C10—C9	121.30 (15)	C16—C18—H18C	110.00
N1—C11—C9	179.09 (19)	H18A—C18—H18B	109.00
O2—C12—C13	123.20 (16)	H18A—C18—H18C	109.00
O2—C12—C17	110.77 (14)	H18B—C18—H18C	109.00
C13—C12—C17	126.03 (16)	C16—C19—H19A	109.00
C12—C13—C14	118.86 (16)	C16—C19—H19B	109.00
C8—C13—C14	118.84 (15)	C16—C19—H19C	109.00
C8—C13—C12	122.28 (15)	H19A—C19—H19B	109.00
O3—C14—C13	121.03 (17)	H19A—C19—H19C	109.00
O3—C14—C15	121.68 (16)	H19B—C19—H19C	109.00
C13—C14—C15	117.26 (15)	O4—C20—C21	122.9 (4)
C14—C15—C16	113.98 (16)	O4—C20—C22	122.7 (4)
C17—C16—C18	108.51 (18)	C21—C20—C22	114.0 (3)
C17—C16—C19	110.37 (18)	C20—C21—H21A	109.00
C18—C16—C19	109.63 (19)	C20—C21—H21B	109.00
C15—C16—C19	110.12 (19)	C20—C21—H21C	109.00
C15—C16—C17	108.13 (17)	H21A—C21—H21B	109.00
C15—C16—C18	110.05 (18)	H21A—C21—H21C	109.00
C12—C17—C16	112.99 (15)	H21B—C21—H21C	109.00
C1—C2—H2	119.00	C20—C22—H22A	109.00
C3—C2—H2	119.00	C20—C22—H22B	109.00
C2—C3—H3	120.00	C20—C22—H22C	109.00
C4—C3—H3	120.00	H22A—C22—H22B	109.00
C4—C5—H5	120.00	H22A—C22—H22C	110.00
C6—C5—H5	120.00	H22B—C22—H22C	109.00

C7—O1—C4—C3	−180.0 (2)	C1—C8—C13—C14	−74.3 (2)
C7—O1—C4—C5	0.2 (3)	C9—C8—C13—C12	−18.5 (2)
C12—O2—C10—N2	172.48 (16)	C9—C8—C13—C14	163.20 (16)
C12—O2—C10—C9	−7.6 (3)	C8—C9—C10—O2	−8.6 (3)
C10—O2—C12—C13	9.5 (3)	C8—C9—C10—N2	171.34 (19)
C10—O2—C12—C17	−171.11 (16)	C11—C9—C10—O2	176.45 (17)
C6—C1—C2—C3	−0.2 (3)	C11—C9—C10—N2	−3.6 (3)
C8—C1—C2—C3	−177.04 (18)	O2—C12—C13—C8	5.1 (3)
C2—C1—C6—C5	0.2 (3)	O2—C12—C13—C14	−176.54 (17)
C8—C1—C6—C5	177.02 (16)	C17—C12—C13—C8	−174.16 (18)
C2—C1—C8—C9	79.6 (2)	C17—C12—C13—C14	4.2 (3)
C2—C1—C8—C13	−41.5 (2)	O2—C12—C17—C16	−161.46 (16)
C6—C1—C8—C9	−97.08 (19)	C13—C12—C17—C16	17.9 (3)
C6—C1—C8—C13	141.80 (17)	C8—C13—C14—O3	0.7 (3)
C1—C2—C3—C4	0.2 (3)	C8—C13—C14—C15	−177.12 (17)
C2—C3—C4—O1	−180.0 (2)	C12—C13—C14—O3	−177.70 (19)
C2—C3—C4—C5	−0.1 (3)	C12—C13—C14—C15	4.5 (3)
O1—C4—C5—C6	179.9 (2)	O3—C14—C15—C16	147.2 (2)
C3—C4—C5—C6	0.1 (3)	C13—C14—C15—C16	−35.0 (3)
C4—C5—C6—C1	−0.1 (3)	C14—C15—C16—C17	54.3 (2)
C1—C8—C9—C10	−103.3 (2)	C14—C15—C16—C18	172.66 (18)
C1—C8—C9—C11	71.7 (2)	C14—C15—C16—C19	−66.4 (2)
C13—C8—C9—C10	20.3 (2)	C15—C16—C17—C12	−45.0 (2)
C13—C8—C9—C11	−164.75 (16)	C18—C16—C17—C12	−164.36 (18)
C1—C8—C13—C12	104.1 (2)	C19—C16—C17—C12	75.5 (2)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the O2/C8–C10/C12/C13) 4H-pyran ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1ⁱ	0.86	2.30	3.142 (3)	168
N2—H2B···O3ⁱⁱ	0.86	2.19	3.029 (2)	165
C6—H6···N1ⁱⁱⁱ	0.93	2.51	3.258 (3)	137
C18—H18A···Cg2^iv	0.96	2.77	3.677 (2)	158

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

Experimental details

Crystal data
Chemical formula	C₁₉H₂₀N₂O₃·C₃H₆O
M_r	382.45
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.2037 (4), 9.5319 (4), 13.8390 (7)
α, β, γ (°)	77.743 (2), 87.307 (3), 80.672 (2)
V (Å³)	1043.43 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.28 × 0.22 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.978, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	16752, 4917, 3284
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.182, 1.04
No. of reflections	4917
No. of parameters	246
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.50

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

Cg2 is the centroid of the O2/C8–C10/C12/C13) 4H-pyran ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1ⁱ	0.86	2.30	3.142 (3)	168
N2—H2B···O3ⁱⁱ	0.86	2.19	3.029 (2)	165
C6—H6···N1ⁱⁱⁱ	0.93	2.51	3.258 (3)	137
C18—H18A···Cg2^iv	0.96	2.77	3.677 (2)	158

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

Acknowledgements

The financial support of the Egyptian Goverment to carry out this study is gratefully acknowledged. We also thank Manchester Metropolitan University and Erciyes University for guidance and instrumental support of the study.

References

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Volume 68| Part 7| July 2012| Pages o2206-o2207

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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