2-Amino-5-oxo-4-phenyl-5,6,7,8-tetra-hydro-4H-chromene-3-carbonitrile.

In the title mol-ecule, C(16)H(14)N(2)O(2), the fused cyclo-hexene and pyran rings adopt an envelope and a flattened boat conformation, respectively. In the crystal, N-H⋯N and N-H⋯O hydrogen bonds link the mol-ecules into corrugated sheets parallel to the bc plane.

Related literature

For the biological activities of substituted pyran derivatives, see: Lokaj et al. (1990 ▶); Marco et al. (1993 ▶). For the crystal structure of a related compound, see: Tu et al. (2001 ▶).

Experimental

Crystal data

C16H14N2O2

M = 266.29

Monoclinic,

a = 20.210 (2) Å

b = 8.8161 (5) Å

c = 16.3862 (13) Å

β = 99.537 (1)°

V = 2879.2 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.32 × 0.21 × 0.15 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.974, T max = 0.988

7077 measured reflections

2535 independent reflections

1083 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.114

S = 0.81

2535 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.11 e Å−3

Data collection: SMART (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: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811008130/cv5040sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008130/cv5040Isup2.hkl

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

C16H14N2O2	F(000) = 1120
Mr = 266.29	Dx = 1.229 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 20.210 (2) Å	Cell parameters from 851 reflections
b = 8.8161 (5) Å	θ = 2.5–19.1°
c = 16.3862 (13) Å	µ = 0.08 mm−1
β = 99.537 (1)°	T = 298 K
V = 2879.2 (4) Å3	Block, red
Z = 8	0.32 × 0.21 × 0.15 mm

Bruker SMART APEX CCD area-detector diffractometer	2535 independent reflections
Radiation source: fine-focus sealed tube	1083 reflections with I > 2σ(I)
graphite	Rint = 0.063
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→17
Tmin = 0.974, Tmax = 0.988	k = −10→10
7077 measured reflections	l = −19→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H-atom parameters constrained
wR(F2) = 0.114	w = 1/[σ2(Fo2) + (0.0454P)2] where P = (Fo2 + 2Fc2)/3
S = 0.81	(Δ/σ)max = 0.001
2535 reflections	Δρmax = 0.12 e Å−3
182 parameters	Δρmin = −0.11 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0017 (2)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
O1	0.10075 (8)	0.98207 (19)	1.01594 (9)	0.0666 (5)
C1	0.07153 (12)	0.8416 (3)	1.00139 (16)	0.0571 (7)
C5	0.09662 (11)	1.0170 (3)	0.87111 (15)	0.0550 (7)
C2	0.05849 (11)	0.7806 (3)	0.92527 (13)	0.0501 (6)
N1	0.05983 (10)	0.7810 (2)	1.07271 (11)	0.0759 (7)
H1A	0.0419	0.6926	1.0729	0.091*
H1B	0.0703	0.8305	1.1182	0.091*
C4	0.08060 (11)	0.8555 (3)	0.85109 (13)	0.0549 (7)
H4	0.0427	0.8528	0.8053	0.066*
O2	0.08103 (10)	1.0779 (2)	0.73126 (12)	0.0897 (7)
C10	0.09649 (13)	1.1227 (3)	0.80287 (19)	0.0686 (8)
C11	0.13891 (14)	0.7707 (3)	0.82384 (15)	0.0569 (7)
C3	0.02554 (13)	0.6406 (4)	0.91435 (14)	0.0586 (7)
C6	0.10774 (12)	1.0700 (3)	0.94811 (17)	0.0604 (7)
N2	−0.00226 (12)	0.5272 (3)	0.90338 (13)	0.0839 (8)
C7	0.12867 (14)	1.2263 (3)	0.97399 (16)	0.0790 (8)
H7A	0.1622	1.2225	1.0237	0.095*
H7B	0.0903	1.2825	0.9865	0.095*
C9	0.11266 (18)	1.2848 (4)	0.82299 (19)	0.1061 (11)
H9A	0.0712	1.3400	0.8232	0.127*
H9B	0.1346	1.3279	0.7799	0.127*
C16	0.13116 (16)	0.6985 (3)	0.74839 (18)	0.0867 (9)
H16	0.0904	0.7056	0.7127	0.104*
C8	0.15751 (17)	1.3064 (3)	0.9057 (2)	0.1100 (12)
H8A	0.1621	1.4139	0.9181	0.132*
H8B	0.2018	1.2663	0.9029	0.132*
C12	0.19982 (16)	0.7600 (3)	0.87459 (18)	0.0894 (10)
H12	0.2064	0.8083	0.9258	0.107*
C15	0.1828 (2)	0.6155 (4)	0.7246 (3)	0.1201 (14)
H15	0.1766	0.5667	0.6736	0.144*
C14	0.2420 (2)	0.6057 (5)	0.7757 (3)	0.1254 (17)
H14	0.2767	0.5492	0.7600	0.150*
C13	0.25165 (18)	0.6783 (5)	0.8505 (3)	0.1215 (14)
H13	0.2930	0.6727	0.8850	0.146*

	U11	U22	U33	U12	U13	U23
O1	0.0811 (13)	0.0612 (12)	0.0571 (11)	−0.0126 (10)	0.0103 (9)	0.0013 (10)
C1	0.0571 (17)	0.0574 (18)	0.0580 (17)	−0.0072 (14)	0.0135 (14)	0.0012 (15)
C5	0.0524 (16)	0.0553 (18)	0.0593 (17)	0.0015 (13)	0.0151 (13)	0.0061 (15)
C2	0.0532 (16)	0.0537 (17)	0.0443 (15)	−0.0037 (13)	0.0104 (12)	−0.0004 (13)
N1	0.1060 (19)	0.0758 (16)	0.0488 (13)	−0.0279 (13)	0.0216 (13)	−0.0051 (12)
C4	0.0530 (16)	0.0653 (18)	0.0462 (15)	−0.0032 (14)	0.0073 (12)	0.0070 (13)
O2	0.1089 (16)	0.0947 (16)	0.0703 (13)	0.0135 (12)	0.0287 (13)	0.0276 (12)
C10	0.071 (2)	0.063 (2)	0.078 (2)	0.0115 (15)	0.0308 (18)	0.0157 (18)
C11	0.0616 (18)	0.0584 (17)	0.0533 (16)	−0.0055 (14)	0.0177 (15)	0.0073 (14)
C3	0.0683 (18)	0.066 (2)	0.0439 (16)	−0.0033 (16)	0.0159 (14)	0.0034 (14)
C6	0.0599 (18)	0.0542 (18)	0.0675 (18)	−0.0019 (14)	0.0115 (14)	0.0077 (16)
N2	0.110 (2)	0.0755 (18)	0.0680 (16)	−0.0249 (16)	0.0210 (14)	−0.0018 (14)
C7	0.084 (2)	0.062 (2)	0.093 (2)	−0.0100 (16)	0.0226 (17)	−0.0057 (17)
C9	0.150 (3)	0.072 (2)	0.110 (3)	0.007 (2)	0.061 (2)	0.019 (2)
C16	0.100 (3)	0.088 (2)	0.076 (2)	−0.0078 (18)	0.0265 (18)	−0.0177 (18)
C8	0.137 (3)	0.064 (2)	0.141 (3)	−0.031 (2)	0.058 (3)	−0.008 (2)
C12	0.066 (2)	0.116 (3)	0.088 (2)	0.015 (2)	0.018 (2)	0.0002 (19)
C15	0.162 (4)	0.091 (3)	0.130 (4)	0.003 (3)	0.089 (3)	−0.020 (2)
C14	0.119 (4)	0.101 (3)	0.181 (5)	0.021 (3)	0.098 (4)	0.025 (3)
C13	0.071 (2)	0.144 (4)	0.155 (4)	0.023 (2)	0.036 (3)	0.018 (3)

O1—C1	1.376 (3)	C6—C7	1.482 (3)
O1—C6	1.381 (3)	C7—C8	1.520 (3)
C1—N1	1.341 (3)	C7—H7A	0.9700
C1—C2	1.344 (3)	C7—H7B	0.9700
C5—C6	1.329 (3)	C9—C8	1.512 (4)
C5—C10	1.455 (3)	C9—H9A	0.9700
C5—C4	1.484 (3)	C9—H9B	0.9700
C2—C3	1.400 (3)	C16—C15	1.382 (4)
C2—C4	1.514 (3)	C16—H16	0.9300
N1—H1A	0.8600	C8—H8A	0.9700
N1—H1B	0.8600	C8—H8B	0.9700
C4—C11	1.524 (3)	C12—C13	1.382 (4)
C4—H4	0.9800	C12—H12	0.9300
O2—C10	1.228 (3)	C15—C14	1.344 (5)
C10—C9	1.491 (4)	C15—H15	0.9300
C11—C12	1.370 (3)	C14—C13	1.368 (5)
C11—C16	1.376 (3)	C14—H14	0.9300
C3—N2	1.146 (3)	C13—H13	0.9300
C1—O1—C6	117.64 (19)	C8—C7—H7A	109.6
N1—C1—C2	127.8 (2)	C6—C7—H7B	109.6
N1—C1—O1	109.9 (2)	C8—C7—H7B	109.6
C2—C1—O1	122.3 (2)	H7A—C7—H7B	108.1
C6—C5—C10	118.9 (3)	C10—C9—C8	113.3 (3)
C6—C5—C4	122.9 (2)	C10—C9—H9A	108.9
C10—C5—C4	118.1 (2)	C8—C9—H9A	108.9
C1—C2—C3	119.2 (2)	C10—C9—H9B	108.9
C1—C2—C4	122.1 (2)	C8—C9—H9B	108.9
C3—C2—C4	118.6 (2)	H9A—C9—H9B	107.7
C1—N1—H1A	120.0	C11—C16—C15	121.3 (3)
C1—N1—H1B	120.0	C11—C16—H16	119.4
H1A—N1—H1B	120.0	C15—C16—H16	119.4
C5—C4—C2	108.9 (2)	C9—C8—C7	110.8 (3)
C5—C4—C11	112.61 (19)	C9—C8—H8A	109.5
C2—C4—C11	111.50 (19)	C7—C8—H8A	109.5
C5—C4—H4	107.9	C9—C8—H8B	109.5
C2—C4—H4	107.9	C7—C8—H8B	109.5
C11—C4—H4	107.9	H8A—C8—H8B	108.1
O2—C10—C5	119.7 (3)	C11—C12—C13	120.6 (3)
O2—C10—C9	122.1 (3)	C11—C12—H12	119.7
C5—C10—C9	118.1 (3)	C13—C12—H12	119.7
C12—C11—C16	118.1 (3)	C14—C15—C16	119.7 (4)
C12—C11—C4	121.1 (2)	C14—C15—H15	120.2
C16—C11—C4	120.8 (3)	C16—C15—H15	120.2
N2—C3—C2	178.2 (3)	C15—C14—C13	120.4 (4)
C5—C6—O1	122.9 (2)	C15—C14—H14	119.8
C5—C6—C7	126.4 (2)	C13—C14—H14	119.8
O1—C6—C7	110.7 (2)	C14—C13—C12	119.9 (4)
C6—C7—C8	110.3 (2)	C14—C13—H13	120.0
C6—C7—H7A	109.6	C12—C13—H13	120.0

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2i	0.86	2.16	3.007 (3)	170
N1—H1B···O2ii	0.86	2.00	2.848 (2)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N2i	0.86	2.16	3.007 (3)	170
N1—H1B⋯O2ii	0.86	2.00	2.848 (2)	169

Symmetry codes: (i) ; (ii) .