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

The 4H-pyran ring of the title compound, C(17)H(16)N(2)O(2), is nearly planar [maximum deviation = 0.077 (2) Å] and the cyclo-hexene ring adopts a flattened chair conformation [puckering parameters: Q(T) = 0.435 (2) Å, θ = 122.0 (3)° and ϕ = 53.5 (3)°]. The 4H-pyran ring is almost perpendicular to the benzene ring [dihedral angle = 87.23 (8)°] and is almost coplanar with the mean plane of the cyclo-hexene ring [dihedral angle = 8.01 (8)°]. In the crystal, inversion-related mol-ecules are linked by pairs of inter-molecular N-H⋯N hydrogen bonds, forming inversion dimers with R(2) (2)(12) ring motifs. These dimers are further connected by N-H⋯O and C-H⋯N hydrogen bonds, forming a layer structure extending parallel to (0-12). Mol-ecules within the layers inter-act with each other via C-H⋯π inter-actions.

Related literature

For the biological background to tetra­hydro-4-chromene and fused tetra­hydro-4-chromene compounds, see: Alvey et al. (2009 ▶); Symeonidis et al. (2009 ▶); Narender & Gupta (2009 ▶). For the synthesis of similar chromene compounds, see: Yadav et al. (2009 ▶); Mohamed et al. (2012a ▶,b ▶,c ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C17H16N2O2

M = 280.32

Triclinic,

a = 8.5931 (9) Å

b = 8.7409 (14) Å

c = 11.0695 (19) Å

α = 72.626 (4)°

β = 70.088 (3)°

γ = 80.035 (6)°

V = 743.71 (19) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.30 × 0.23 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.975, T max = 0.984

8982 measured reflections

2916 independent reflections

1704 reflections with I > 2σ(I)

R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.115

S = 0.91

2916 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.17 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812029480/sj5250sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029480/sj5250Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029480/sj5250Isup3.cml

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

C17H16N2O2	Z = 2
Mr = 280.32	F(000) = 296
Triclinic, P1	Dx = 1.252 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5931 (9) Å	Cell parameters from 245 reflections
b = 8.7409 (14) Å	θ = 3.2–18°
c = 11.0695 (19) Å	µ = 0.08 mm−1
α = 72.626 (4)°	T = 296 K
β = 70.088 (3)°	Prism, white
γ = 80.035 (6)°	0.30 × 0.23 × 0.20 mm
V = 743.71 (19) Å3

Bruker Kappa APEXII CCD diffractometer	2916 independent reflections
Radiation source: fine-focus sealed tube	1704 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.075
Detector resolution: 0.81 pixels mm-1	θmax = 26.0°, θmin = 2.0°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −10→10
Tmin = 0.975, Tmax = 0.984	l = −13→13
8982 measured reflections

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) = 0.115	H-atom parameters constrained
S = 0.91	w = 1/[σ2(Fo2) + (0.0535P)2] where P = (Fo2 + 2Fc2)/3
2916 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	−0.07181 (12)	0.43638 (14)	0.69952 (11)	0.0628 (4)
O2	0.48905 (15)	0.45532 (14)	0.66064 (13)	0.0747 (5)
N1	0.17338 (17)	0.0029 (2)	0.50277 (16)	0.0766 (7)
N2	−0.17035 (15)	0.27899 (18)	0.62146 (15)	0.0698 (6)
C1	0.31349 (18)	0.13607 (18)	0.74881 (16)	0.0458 (6)
C2	0.46472 (18)	0.04982 (19)	0.71440 (17)	0.0543 (6)
C3	0.5138 (2)	−0.0768 (2)	0.8064 (2)	0.0625 (7)
C4	0.4143 (2)	−0.1234 (2)	0.93584 (19)	0.0590 (7)
C5	0.2636 (2)	−0.0370 (2)	0.97073 (18)	0.0657 (7)
C6	0.2129 (2)	0.0905 (2)	0.87951 (18)	0.0600 (7)
C7	0.4678 (3)	−0.2645 (2)	1.0359 (2)	0.0882 (9)
C8	0.25982 (17)	0.27363 (18)	0.64590 (16)	0.0469 (5)
C9	0.11699 (18)	0.23365 (18)	0.61288 (15)	0.0478 (6)
C10	0.14572 (18)	0.1067 (2)	0.55221 (17)	0.0546 (6)
C11	−0.03611 (19)	0.3100 (2)	0.64164 (16)	0.0510 (6)
C12	0.0570 (2)	0.49540 (19)	0.71581 (16)	0.0532 (6)
C13	0.21195 (19)	0.42714 (18)	0.68865 (16)	0.0501 (6)
C14	0.3443 (2)	0.5090 (2)	0.69385 (17)	0.0606 (7)
C15	0.2972 (3)	0.6633 (2)	0.7339 (2)	0.0896 (10)
C16	0.1214 (3)	0.6772 (3)	0.8221 (2)	0.0916 (10)
C17	−0.0012 (2)	0.6426 (2)	0.7642 (2)	0.0730 (8)
H2	0.53500	0.07760	0.62750	0.0650*
H2A	−0.16480	0.20220	0.58610	0.0840*
H2B	−0.26260	0.33580	0.64380	0.0840*
H3	0.61690	−0.13230	0.78020	0.0750*
H5	0.19410	−0.06510	1.05790	0.0790*
H6	0.11000	0.14640	0.90610	0.0720*
H7A	0.46800	−0.22940	1.11020	0.1320*
H7B	0.57750	−0.30710	0.99470	0.1320*
H7C	0.39190	−0.34660	1.06630	0.1320*
H8	0.35430	0.29220	0.56420	0.0560*
H15A	0.31220	0.75200	0.65440	0.1080*
H15B	0.37140	0.67300	0.78000	0.1080*
H16A	0.09460	0.78500	0.83470	0.1100*
H16B	0.11120	0.60230	0.90860	0.1100*
H17A	−0.10870	0.62860	0.83160	0.0880*
H17B	−0.01380	0.73320	0.69100	0.0880*

	U11	U22	U33	U12	U13	U23
O1	0.0490 (6)	0.0667 (8)	0.0832 (9)	0.0047 (6)	−0.0251 (6)	−0.0344 (7)
O2	0.0619 (8)	0.0720 (9)	0.0993 (11)	−0.0152 (7)	−0.0439 (7)	−0.0076 (8)
N1	0.0584 (9)	0.0903 (12)	0.1034 (14)	0.0059 (8)	−0.0308 (9)	−0.0570 (11)
N2	0.0474 (8)	0.0865 (11)	0.0946 (12)	0.0048 (7)	−0.0334 (8)	−0.0434 (10)
C1	0.0436 (8)	0.0481 (10)	0.0555 (11)	−0.0082 (7)	−0.0234 (8)	−0.0154 (8)
C2	0.0481 (9)	0.0560 (11)	0.0611 (12)	−0.0029 (8)	−0.0190 (8)	−0.0165 (9)
C3	0.0561 (10)	0.0559 (11)	0.0830 (15)	0.0054 (8)	−0.0338 (10)	−0.0200 (11)
C4	0.0720 (12)	0.0509 (11)	0.0668 (14)	−0.0103 (9)	−0.0387 (11)	−0.0105 (10)
C5	0.0681 (12)	0.0726 (13)	0.0562 (12)	−0.0116 (10)	−0.0232 (9)	−0.0085 (10)
C6	0.0503 (9)	0.0679 (12)	0.0623 (13)	−0.0004 (8)	−0.0202 (9)	−0.0166 (10)
C7	0.1123 (17)	0.0642 (13)	0.0970 (16)	−0.0023 (12)	−0.0601 (13)	−0.0042 (12)
C8	0.0406 (8)	0.0533 (10)	0.0510 (10)	−0.0051 (7)	−0.0192 (7)	−0.0128 (8)
C9	0.0471 (9)	0.0521 (10)	0.0512 (10)	−0.0020 (7)	−0.0218 (7)	−0.0168 (9)
C10	0.0412 (9)	0.0674 (12)	0.0648 (12)	0.0009 (8)	−0.0240 (8)	−0.0252 (10)
C11	0.0471 (9)	0.0579 (11)	0.0553 (11)	−0.0020 (8)	−0.0227 (8)	−0.0184 (9)
C12	0.0593 (10)	0.0506 (10)	0.0574 (11)	−0.0043 (8)	−0.0262 (8)	−0.0154 (9)
C13	0.0554 (10)	0.0466 (10)	0.0542 (11)	−0.0068 (8)	−0.0278 (8)	−0.0072 (8)
C14	0.0668 (12)	0.0536 (11)	0.0692 (13)	−0.0112 (9)	−0.0391 (10)	−0.0027 (9)
C15	0.1010 (16)	0.0667 (14)	0.129 (2)	−0.0138 (12)	−0.0598 (15)	−0.0332 (14)
C16	0.1157 (19)	0.0743 (15)	0.1070 (18)	−0.0041 (13)	−0.0471 (15)	−0.0426 (14)
C17	0.0797 (13)	0.0606 (12)	0.0857 (15)	0.0013 (10)	−0.0297 (11)	−0.0281 (11)

O1—C11	1.377 (2)	C12—C13	1.334 (2)
O1—C12	1.383 (2)	C13—C14	1.470 (3)
O2—C14	1.222 (2)	C14—C15	1.492 (3)
N1—C10	1.146 (2)	C15—C16	1.501 (3)
N2—C11	1.332 (2)	C16—C17	1.516 (3)
N2—H2A	0.8600	C2—H2	0.9300
N2—H2B	0.8600	C3—H3	0.9300
C1—C8	1.518 (2)	C5—H5	0.9300
C1—C2	1.378 (2)	C6—H6	0.9300
C1—C6	1.386 (2)	C7—H7A	0.9600
C2—C3	1.378 (3)	C7—H7B	0.9600
C3—C4	1.374 (3)	C7—H7C	0.9600
C4—C7	1.515 (3)	C8—H8	0.9800
C4—C5	1.375 (3)	C15—H15A	0.9700
C5—C6	1.382 (3)	C15—H15B	0.9700
C8—C9	1.514 (2)	C16—H16A	0.9700
C8—C13	1.500 (2)	C16—H16B	0.9700
C9—C10	1.407 (2)	C17—H17A	0.9700
C9—C11	1.347 (2)	C17—H17B	0.9700
C12—C17	1.483 (2)
C11—O1—C12	118.57 (13)	C15—C16—C17	112.04 (18)
H2A—N2—H2B	120.00	C12—C17—C16	110.62 (17)
C11—N2—H2A	120.00	C1—C2—H2	119.00
C11—N2—H2B	120.00	C3—C2—H2	119.00
C2—C1—C6	117.40 (15)	C2—C3—H3	119.00
C6—C1—C8	121.94 (15)	C4—C3—H3	119.00
C2—C1—C8	120.65 (15)	C4—C5—H5	119.00
C1—C2—C3	121.21 (16)	C6—C5—H5	119.00
C2—C3—C4	121.73 (17)	C1—C6—H6	120.00
C3—C4—C7	121.45 (17)	C5—C6—H6	120.00
C3—C4—C5	117.22 (17)	C4—C7—H7A	109.00
C5—C4—C7	121.33 (18)	C4—C7—H7B	110.00
C4—C5—C6	121.66 (17)	C4—C7—H7C	110.00
C1—C6—C5	120.78 (17)	H7A—C7—H7B	109.00
C9—C8—C13	109.01 (13)	H7A—C7—H7C	109.00
C1—C8—C9	111.87 (13)	H7B—C7—H7C	109.00
C1—C8—C13	112.47 (13)	C1—C8—H8	108.00
C8—C9—C10	117.75 (14)	C9—C8—H8	108.00
C8—C9—C11	123.56 (15)	C13—C8—H8	108.00
C10—C9—C11	118.67 (16)	C14—C15—H15A	109.00
N1—C10—C9	178.20 (19)	C14—C15—H15B	109.00
N2—C11—C9	127.76 (17)	C16—C15—H15A	109.00
O1—C11—N2	110.71 (15)	C16—C15—H15B	109.00
O1—C11—C9	121.53 (15)	H15A—C15—H15B	108.00
O1—C12—C17	110.90 (15)	C15—C16—H16A	109.00
O1—C12—C13	123.06 (15)	C15—C16—H16B	109.00
C13—C12—C17	126.03 (17)	C17—C16—H16A	109.00
C8—C13—C12	122.92 (16)	C17—C16—H16B	109.00
C8—C13—C14	117.92 (15)	H16A—C16—H16B	108.00
C12—C13—C14	119.08 (15)	C12—C17—H17A	110.00
C13—C14—C15	117.94 (17)	C12—C17—H17B	109.00
O2—C14—C13	120.64 (16)	C16—C17—H17A	110.00
O2—C14—C15	121.34 (18)	C16—C17—H17B	109.00
C14—C15—C16	113.52 (19)	H17A—C17—H17B	108.00
C11—O1—C12—C17	173.14 (14)	C1—C8—C9—C10	−64.06 (19)
C12—O1—C11—N2	−173.77 (14)	C1—C8—C13—C14	70.02 (19)
C12—O1—C11—C9	6.5 (2)	C9—C8—C13—C12	11.5 (2)
C11—O1—C12—C13	−5.9 (2)	C9—C8—C13—C14	−165.32 (14)
C8—C1—C2—C3	−179.03 (16)	C8—C9—C11—N2	−177.03 (16)
C2—C1—C6—C5	−0.2 (3)	C10—C9—C11—O1	−179.21 (15)
C8—C1—C6—C5	178.89 (16)	C10—C9—C11—N2	1.1 (3)
C6—C1—C2—C3	0.0 (3)	C8—C9—C11—O1	2.6 (2)
C2—C1—C8—C9	110.95 (17)	O1—C12—C13—C8	−4.0 (3)
C2—C1—C8—C13	−125.98 (17)	O1—C12—C13—C14	172.80 (14)
C6—C1—C8—C9	−68.1 (2)	C17—C12—C13—C8	177.11 (16)
C6—C1—C8—C13	55.0 (2)	C17—C12—C13—C14	−6.1 (3)
C1—C2—C3—C4	0.4 (3)	O1—C12—C17—C16	162.42 (15)
C2—C3—C4—C5	−0.8 (3)	C13—C12—C17—C16	−18.6 (3)
C2—C3—C4—C7	178.95 (18)	C8—C13—C14—O2	2.0 (2)
C3—C4—C5—C6	0.6 (3)	C8—C13—C14—C15	178.87 (15)
C7—C4—C5—C6	−179.08 (18)	C12—C13—C14—O2	−174.91 (16)
C4—C5—C6—C1	−0.2 (3)	C12—C13—C14—C15	1.9 (2)
C1—C8—C9—C11	114.11 (17)	O2—C14—C15—C16	−156.13 (19)
C13—C8—C9—C10	170.93 (14)	C13—C14—C15—C16	27.0 (2)
C13—C8—C9—C11	−10.9 (2)	C14—C15—C16—C17	−51.4 (2)
C1—C8—C13—C12	−113.18 (18)	C15—C16—C17—C12	46.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1i	0.86	2.31	3.168 (2)	175
N2—H2B···O2ii	0.86	2.18	3.017 (2)	164
C2—H2···N1iii	0.93	2.53	3.277 (2)	138
C6—H6···Cg1	0.93	2.79	3.128 (2)	102
C7—H7A···Cg2iv	0.96	2.87	3.640 (2)	138

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the 4H-pyran ring (O1/C8/C9/C11–C13) and the benzene ring (C1–C6), respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1i	0.86	2.31	3.168 (2)	175
N2—H2B⋯O2ii	0.86	2.18	3.017 (2)	164
C2—H2⋯N1iii	0.93	2.53	3.277 (2)	138
C6—H6⋯Cg1	0.93	2.79	3.128 (2)	102
C7—H7A⋯Cg2iv	0.96	2.87	3.640 (2)	138

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .