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

In the title mol-ecule, C(18)H(19)N(3)O(2), the fused cyclo-hexenone and pyran rings adopt sofa conformations. Inter-molecular N-H⋯N and N-H⋯O hydrogen bonds link mol-ecules into corrugated layers parallel to the bc plane.

Related literature

For the crystal structures of related compounds, see: Kong et al. (2011 ▶); Wang (2011 ▶).

Experimental

Crystal data

C18H19N3O2

M = 309.36

Monoclinic,

a = 25.021 (3) Å

b = 8.8724 (8) Å

c = 16.3827 (16) Å

β = 114.721 (2)°

V = 3303.5 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.40 × 0.36 × 0.22 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.968, T max = 0.982

8056 measured reflections

2907 independent reflections

1411 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.187

S = 1.01

2907 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.21 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811043662/cv5176sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043662/cv5176Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811043662/cv5176Isup3.cml

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

C18H19N3O2	F(000) = 1312
Mr = 309.36	Dx = 1.244 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 25.021 (3) Å	Cell parameters from 1265 reflections
b = 8.8724 (8) Å	θ = 2.5–21.3°
c = 16.3827 (16) Å	µ = 0.08 mm−1
β = 114.721 (2)°	T = 298 K
V = 3303.5 (5) Å3	Block, red
Z = 8	0.40 × 0.36 × 0.22 mm

Bruker SMART APEX CCD area-detector diffractometer	2907 independent reflections
Radiation source: fine-focus sealed tube	1411 reflections with I > 2σ(I)
graphite	Rint = 0.062
phi and ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −29→25
Tmin = 0.968, Tmax = 0.982	k = −10→8
8056 measured reflections	l = −19→19

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.187	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0818P)2 + 1.1159P] where P = (Fo2 + 2Fc2)/3
2907 reflections	(Δ/σ)max < 0.001
210 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
N1	0.05600 (14)	0.2235 (3)	−0.03033 (19)	0.0617 (9)
H1A	0.0417	0.3129	−0.0433	0.074*
H1B	0.0652	0.1742	−0.0679	0.074*
N2	0.00475 (15)	0.4788 (4)	0.0962 (2)	0.0641 (10)
N3	0.23314 (16)	0.5169 (4)	0.4808 (3)	0.0788 (11)
O1	0.08809 (11)	0.0187 (2)	0.05519 (15)	0.0530 (7)
O2	0.07367 (12)	−0.0804 (3)	0.32595 (18)	0.0683 (8)
C1	0.06404 (14)	0.1610 (4)	0.0482 (2)	0.0422 (9)
C2	0.05254 (14)	0.2195 (3)	0.1146 (2)	0.0389 (8)
C3	0.06843 (14)	0.1431 (3)	0.2039 (2)	0.0383 (8)
H3	0.0327	0.1385	0.2145	0.046*
C4	0.08682 (14)	−0.0157 (3)	0.1978 (2)	0.0390 (8)
C5	0.08851 (16)	−0.1218 (4)	0.2673 (3)	0.0543 (10)
C6	0.1057 (2)	−0.2815 (4)	0.2617 (3)	0.0838 (15)
H6A	0.0704	−0.3419	0.2335	0.101*
H6B	0.1276	−0.3199	0.3220	0.101*
C7	0.1428 (2)	−0.2992 (4)	0.2089 (3)	0.0866 (15)
H7A	0.1814	−0.2557	0.2427	0.104*
H7B	0.1479	−0.4055	0.2003	0.104*
C8	0.11417 (18)	−0.2228 (4)	0.1188 (3)	0.0613 (11)
H8A	0.1417	−0.2193	0.0911	0.074*
H8B	0.0801	−0.2805	0.0799	0.074*
C9	0.09573 (14)	−0.0674 (4)	0.1286 (2)	0.0449 (9)
C10	0.02665 (16)	0.3637 (4)	0.1031 (2)	0.0428 (9)
C11	0.11413 (14)	0.2331 (3)	0.2807 (2)	0.0386 (8)
C12	0.16973 (16)	0.2606 (4)	0.2860 (3)	0.0555 (10)
H12	0.1808	0.2171	0.2438	0.067*
C13	0.20934 (17)	0.3510 (4)	0.3524 (3)	0.0633 (11)
H13	0.2464	0.3673	0.3537	0.076*
C14	0.19513 (17)	0.4180 (4)	0.4172 (3)	0.0522 (10)
C15	0.13956 (18)	0.3880 (4)	0.4126 (2)	0.0572 (10)
H15	0.1283	0.4297	0.4551	0.069*
C16	0.10079 (15)	0.2973 (4)	0.3461 (2)	0.0490 (9)
H16	0.0640	0.2788	0.3454	0.059*
C17	0.2940 (2)	0.5246 (5)	0.4932 (4)	0.1074 (19)
H17A	0.3129	0.4299	0.5158	0.161*
H17B	0.3139	0.6030	0.5354	0.161*
H17C	0.2953	0.5460	0.4367	0.161*
C18	0.2225 (2)	0.5576 (6)	0.5575 (3)	0.1047 (18)
H18A	0.1839	0.6007	0.5377	0.157*
H18B	0.2513	0.6299	0.5932	0.157*
H18C	0.2251	0.4694	0.5929	0.157*

	U11	U22	U33	U12	U13	U23
N1	0.104 (3)	0.0475 (19)	0.046 (2)	0.0274 (17)	0.0439 (19)	0.0138 (15)
N2	0.092 (3)	0.048 (2)	0.059 (2)	0.0198 (19)	0.038 (2)	0.0132 (16)
N3	0.069 (3)	0.064 (2)	0.079 (3)	−0.0101 (19)	0.006 (2)	−0.019 (2)
O1	0.0782 (18)	0.0426 (15)	0.0480 (16)	0.0211 (13)	0.0360 (14)	0.0096 (12)
O2	0.097 (2)	0.0645 (18)	0.0472 (17)	−0.0115 (15)	0.0338 (16)	0.0095 (14)
C1	0.050 (2)	0.038 (2)	0.040 (2)	0.0075 (16)	0.0202 (17)	0.0037 (16)
C2	0.045 (2)	0.037 (2)	0.0331 (19)	0.0050 (15)	0.0149 (16)	0.0038 (15)
C3	0.042 (2)	0.0386 (19)	0.037 (2)	0.0015 (15)	0.0187 (16)	0.0036 (15)
C4	0.047 (2)	0.0325 (19)	0.0336 (19)	−0.0056 (15)	0.0128 (16)	0.0051 (15)
C5	0.066 (3)	0.046 (2)	0.040 (2)	−0.0094 (19)	0.011 (2)	0.0049 (18)
C6	0.139 (4)	0.039 (2)	0.061 (3)	0.002 (2)	0.030 (3)	0.015 (2)
C7	0.120 (4)	0.046 (3)	0.081 (3)	0.025 (3)	0.029 (3)	0.016 (2)
C8	0.074 (3)	0.040 (2)	0.067 (3)	0.0051 (19)	0.027 (2)	0.0000 (19)
C9	0.052 (2)	0.035 (2)	0.045 (2)	0.0021 (16)	0.0178 (18)	0.0088 (17)
C10	0.060 (2)	0.039 (2)	0.033 (2)	0.0017 (18)	0.0232 (17)	0.0030 (16)
C11	0.044 (2)	0.0339 (19)	0.036 (2)	0.0044 (15)	0.0153 (16)	0.0061 (15)
C12	0.049 (2)	0.064 (3)	0.058 (3)	−0.001 (2)	0.026 (2)	−0.007 (2)
C13	0.042 (2)	0.070 (3)	0.074 (3)	−0.004 (2)	0.021 (2)	−0.008 (2)
C14	0.056 (3)	0.033 (2)	0.052 (2)	0.0002 (18)	0.008 (2)	0.0012 (18)
C15	0.073 (3)	0.051 (2)	0.051 (2)	−0.005 (2)	0.029 (2)	−0.0125 (19)
C16	0.049 (2)	0.052 (2)	0.048 (2)	−0.0072 (18)	0.0225 (19)	−0.0072 (18)
C17	0.062 (3)	0.083 (4)	0.132 (5)	−0.018 (3)	−0.003 (3)	−0.018 (3)
C18	0.124 (4)	0.085 (3)	0.072 (4)	−0.020 (3)	0.009 (3)	−0.037 (3)

N1—C1	1.337 (4)	C7—C8	1.505 (5)
N1—H1A	0.8600	C7—H7A	0.9700
N1—H1B	0.8600	C7—H7B	0.9700
N2—C10	1.141 (4)	C8—C9	1.484 (5)
N3—C14	1.390 (5)	C8—H8A	0.9700
N3—C18	1.435 (6)	C8—H8B	0.9700
N3—C17	1.450 (5)	C11—C16	1.372 (4)
O1—C9	1.369 (4)	C11—C12	1.379 (5)
O1—C1	1.383 (4)	C12—C13	1.381 (5)
O2—C5	1.222 (4)	C12—H12	0.9300
C1—C2	1.341 (4)	C13—C14	1.387 (5)
C2—C10	1.411 (5)	C13—H13	0.9300
C2—C3	1.507 (4)	C14—C15	1.386 (5)
C3—C4	1.498 (4)	C15—C16	1.376 (5)
C3—C11	1.524 (4)	C15—H15	0.9300
C3—H3	0.9800	C16—H16	0.9300
C4—C9	1.326 (4)	C17—H17A	0.9600
C4—C5	1.464 (5)	C17—H17B	0.9600
C5—C6	1.495 (5)	C17—H17C	0.9600
C6—C7	1.517 (6)	C18—H18A	0.9600
C6—H6A	0.9700	C18—H18B	0.9600
C6—H6B	0.9700	C18—H18C	0.9600
C1—N1—H1A	120.0	C7—C8—H8A	109.5
C1—N1—H1B	120.0	C9—C8—H8B	109.5
H1A—N1—H1B	120.0	C7—C8—H8B	109.5
C14—N3—C18	119.7 (4)	H8A—C8—H8B	108.1
C14—N3—C17	118.9 (4)	C4—C9—O1	123.1 (3)
C18—N3—C17	115.7 (4)	C4—C9—C8	125.8 (3)
C9—O1—C1	118.6 (2)	O1—C9—C8	111.1 (3)
N1—C1—C2	128.6 (3)	N2—C10—C2	177.2 (4)
N1—C1—O1	110.1 (3)	C16—C11—C12	116.5 (3)
C2—C1—O1	121.3 (3)	C16—C11—C3	121.2 (3)
C1—C2—C10	119.0 (3)	C12—C11—C3	122.3 (3)
C1—C2—C3	123.7 (3)	C11—C12—C13	121.7 (3)
C10—C2—C3	117.3 (3)	C11—C12—H12	119.2
C4—C3—C2	108.8 (3)	C13—C12—H12	119.2
C4—C3—C11	113.7 (3)	C12—C13—C14	121.5 (4)
C2—C3—C11	111.5 (3)	C12—C13—H13	119.2
C4—C3—H3	107.5	C14—C13—H13	119.2
C2—C3—H3	107.5	C15—C14—C13	116.6 (3)
C11—C3—H3	107.5	C15—C14—N3	121.2 (4)
C9—C4—C5	118.8 (3)	C13—C14—N3	122.1 (4)
C9—C4—C3	123.3 (3)	C16—C15—C14	121.0 (3)
C5—C4—C3	117.6 (3)	C16—C15—H15	119.5
O2—C5—C4	119.9 (3)	C14—C15—H15	119.5
O2—C5—C6	121.6 (3)	C11—C16—C15	122.7 (3)
C4—C5—C6	118.5 (4)	C11—C16—H16	118.6
C5—C6—C7	113.2 (3)	C15—C16—H16	118.6
C5—C6—H6A	108.9	N3—C17—H17A	109.5
C7—C6—H6A	108.9	N3—C17—H17B	109.5
C5—C6—H6B	108.9	H17A—C17—H17B	109.5
C7—C6—H6B	108.9	N3—C17—H17C	109.5
H6A—C6—H6B	107.8	H17A—C17—H17C	109.5
C8—C7—C6	111.0 (4)	H17B—C17—H17C	109.5
C8—C7—H7A	109.4	N3—C18—H18A	109.5
C6—C7—H7A	109.4	N3—C18—H18B	109.5
C8—C7—H7B	109.4	H18A—C18—H18B	109.5
C6—C7—H7B	109.4	N3—C18—H18C	109.5
H7A—C7—H7B	108.0	H18A—C18—H18C	109.5
C9—C8—C7	110.8 (3)	H18B—C18—H18C	109.5
C9—C8—H8A	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2i	0.86	2.16	3.014 (4)	171.
N1—H1B···O2ii	0.86	2.02	2.867 (4)	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	3.014 (4)	171
N1—H1B⋯O2ii	0.86	2.02	2.867 (4)	169

Symmetry codes: (i) ; (ii) .