2-Amino-4-(2-chloro-phen-yl)-5,10-dioxo-5,10-dihydro-4H-benzo[g]chromene-3-carbonitrile.

In the mol-ecule of the title compound, C(20)H(11)ClN(2)O(3), the pyran ring adopts a flattened-boat conformation. In the crystal structure, inter-molecular N-H⋯N and N-H⋯O hydrogen bonds generate edge-fused R(2) (2)(12) and R(2) (2)(14) ring motifs; the hydrogen-bonded motifs are linked to each other, forming a three-dimensional network. A π-π contact [centroid-to-centroid distance = 3.879 (3) Å] between the chloro-phenyl rings may further stabilize the structure.

Related literature

For background to the biological activity of pyran and naphthoquinone compounds, see: El-Agrody et al. (2000 ▶); Mohr et al. (1975 ▶); Banzatti et al. (1984 ▶); Hatakeyama et al. (1988 ▶); Tandon et al. (1991 ▶); Kongkathip et al. (2003 ▶). 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

C20H11ClN2O3

M = 362.76

Triclinic,

a = 8.3201 (10) Å

b = 9.3729 (12) Å

c = 11.0081 (16) Å

α = 93.015 (1)°

β = 96.393 (1)°

γ = 110.732 (2)°

V = 793.95 (18) Å3

Z = 2

Mo Kα radiation

μ = 0.27 mm−1

T = 298 (2) K

0.17 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.956, T max = 0.974

4207 measured reflections

2746 independent reflections

1566 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.100

S = 1.04

2746 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808039986/hk2585sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039986/hk2585Isup2.hkl

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

C20H11ClN2O3	Z = 2
Mr = 362.76	F(000) = 372
Triclinic, P1	Dx = 1.517 Mg m−3
Hall symbol: -P 1	Melting point > 573 K
a = 8.3201 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.3729 (12) Å	Cell parameters from 959 reflections
c = 11.0081 (16) Å	θ = 2.8–25.1°
α = 93.015 (1)°	µ = 0.27 mm−1
β = 96.393 (1)°	T = 298 K
γ = 110.732 (2)°	Block, orange
V = 793.95 (18) Å3	0.17 × 0.15 × 0.10 mm

Bruker SMART CCD area-detector diffractometer	2746 independent reflections
Radiation source: fine-focus sealed tube	1566 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.956, Tmax = 0.974	k = −11→10
4207 measured reflections	l = −13→8

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0295P)2] where P = (Fo2 + 2Fc2)/3
2746 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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
Cl1	−0.01619 (12)	0.04001 (10)	0.69113 (9)	0.0587 (3)
O1	0.1440 (3)	0.3890 (2)	0.6133 (2)	0.0405 (6)
O2	0.5886 (3)	0.2063 (3)	0.7464 (2)	0.0541 (7)
O3	0.2251 (3)	0.3753 (3)	0.3898 (2)	0.0536 (7)
N1	−0.0034 (3)	0.4822 (3)	0.7313 (2)	0.0471 (8)
H1A	−0.0304	0.5099	0.7994	0.057*
H1B	−0.0556	0.4936	0.6626	0.057*
N2	0.1921 (4)	0.4871 (4)	1.0491 (3)	0.0578 (9)
C1	0.1196 (4)	0.4216 (3)	0.7320 (3)	0.0369 (8)
C2	0.2135 (4)	0.3957 (3)	0.8299 (3)	0.0344 (8)
C3	0.3297 (4)	0.3028 (3)	0.8197 (3)	0.0336 (8)
H3	0.4412	0.3622	0.8696	0.040*
C4	0.3646 (4)	0.2940 (3)	0.6883 (3)	0.0309 (8)
C5	0.5061 (4)	0.2424 (3)	0.6626 (3)	0.0360 (8)
C6	0.5448 (4)	0.2361 (3)	0.5342 (3)	0.0339 (8)
C7	0.6774 (4)	0.1889 (4)	0.5076 (3)	0.0466 (9)
H7	0.7416	0.1604	0.5699	0.056*
C8	0.7152 (5)	0.1837 (4)	0.3890 (3)	0.0538 (10)
H8	0.8064	0.1540	0.3718	0.065*
C9	0.6180 (4)	0.2225 (4)	0.2961 (3)	0.0530 (10)
H9	0.6426	0.2170	0.2160	0.064*
C10	0.4851 (4)	0.2690 (4)	0.3207 (3)	0.0461 (9)
H10	0.4202	0.2951	0.2574	0.055*
C11	0.4476 (4)	0.2770 (3)	0.4401 (3)	0.0346 (8)
C12	0.3083 (4)	0.3326 (3)	0.4679 (3)	0.0350 (8)
C13	0.2762 (4)	0.3374 (3)	0.5983 (3)	0.0337 (8)
C14	0.1989 (4)	0.4470 (4)	0.9505 (3)	0.0405 (9)
C15	0.2617 (4)	0.1487 (3)	0.8721 (3)	0.0322 (8)
C16	0.1126 (4)	0.0269 (4)	0.8235 (3)	0.0374 (9)
C17	0.0573 (4)	−0.1101 (4)	0.8767 (3)	0.0450 (9)
H17	−0.0427	−0.1903	0.8412	0.054*
C18	0.1515 (5)	−0.1260 (4)	0.9819 (3)	0.0538 (10)
H18	0.1157	−0.2177	1.0179	0.065*
C19	0.2985 (5)	−0.0068 (4)	1.0343 (3)	0.0514 (10)
H19	0.3613	−0.0172	1.1065	0.062*
C20	0.3530 (4)	0.1287 (4)	0.9798 (3)	0.0433 (9)
H20	0.4532	0.2084	1.0158	0.052*

	U11	U22	U33	U12	U13	U23
Cl1	0.0512 (6)	0.0542 (6)	0.0649 (7)	0.0171 (4)	−0.0099 (5)	0.0082 (5)
O1	0.0409 (14)	0.0529 (14)	0.0391 (14)	0.0302 (12)	0.0069 (11)	0.0067 (12)
O2	0.0534 (16)	0.0759 (17)	0.0500 (16)	0.0423 (14)	0.0080 (13)	0.0191 (14)
O3	0.0643 (17)	0.0733 (17)	0.0398 (15)	0.0459 (14)	0.0020 (13)	0.0114 (13)
N1	0.0525 (19)	0.0636 (19)	0.0407 (18)	0.0403 (16)	0.0056 (15)	0.0031 (16)
N2	0.065 (2)	0.066 (2)	0.046 (2)	0.0297 (18)	0.0090 (18)	−0.0059 (18)
C1	0.037 (2)	0.0340 (19)	0.044 (2)	0.0177 (16)	0.0102 (18)	0.0047 (17)
C2	0.037 (2)	0.0356 (19)	0.035 (2)	0.0183 (16)	0.0072 (17)	0.0027 (17)
C3	0.0340 (19)	0.0366 (19)	0.033 (2)	0.0165 (15)	0.0015 (16)	0.0036 (17)
C4	0.0328 (19)	0.0285 (17)	0.034 (2)	0.0135 (15)	0.0057 (16)	0.0044 (16)
C5	0.0319 (19)	0.0350 (19)	0.044 (2)	0.0162 (16)	0.0015 (18)	0.0081 (18)
C6	0.033 (2)	0.0334 (18)	0.036 (2)	0.0121 (15)	0.0061 (17)	0.0041 (17)
C7	0.043 (2)	0.053 (2)	0.054 (3)	0.0278 (18)	0.0078 (19)	0.008 (2)
C8	0.049 (2)	0.065 (3)	0.055 (3)	0.028 (2)	0.016 (2)	−0.002 (2)
C9	0.051 (2)	0.065 (3)	0.044 (2)	0.021 (2)	0.010 (2)	−0.001 (2)
C10	0.043 (2)	0.054 (2)	0.044 (2)	0.0207 (18)	0.0074 (19)	0.003 (2)
C11	0.035 (2)	0.0324 (19)	0.035 (2)	0.0108 (15)	0.0047 (17)	−0.0009 (17)
C12	0.035 (2)	0.0325 (19)	0.039 (2)	0.0132 (15)	0.0047 (17)	0.0037 (17)
C13	0.0346 (19)	0.0297 (18)	0.040 (2)	0.0158 (15)	0.0061 (17)	0.0012 (17)
C14	0.039 (2)	0.037 (2)	0.048 (2)	0.0164 (16)	0.0055 (19)	0.008 (2)
C15	0.0331 (19)	0.0377 (19)	0.0338 (19)	0.0207 (16)	0.0098 (16)	0.0064 (17)
C16	0.036 (2)	0.042 (2)	0.042 (2)	0.0234 (16)	0.0058 (17)	0.0035 (18)
C17	0.041 (2)	0.036 (2)	0.062 (3)	0.0163 (16)	0.0148 (19)	0.0048 (19)
C18	0.062 (3)	0.050 (2)	0.063 (3)	0.031 (2)	0.021 (2)	0.023 (2)
C19	0.059 (3)	0.059 (3)	0.046 (2)	0.032 (2)	0.009 (2)	0.015 (2)
C20	0.045 (2)	0.047 (2)	0.040 (2)	0.0190 (17)	0.0035 (18)	0.0086 (18)

Cl1—C16	1.747 (3)	C7—C8	1.379 (5)
O1—C1	1.380 (4)	C7—H7	0.9300
O1—C13	1.370 (3)	C8—C9	1.377 (4)
O2—C5	1.223 (3)	C8—H8	0.9300
O3—C12	1.216 (3)	C9—C10	1.372 (4)
N1—C1	1.334 (3)	C9—H9	0.9300
N1—H1A	0.8600	C10—C11	1.389 (4)
N1—H1B	0.8600	C10—H10	0.9300
N2—C14	1.144 (4)	C11—C12	1.482 (4)
C1—C2	1.343 (4)	C12—C13	1.490 (4)
C2—C14	1.420 (5)	C15—C16	1.383 (4)
C2—C3	1.522 (4)	C15—C20	1.393 (4)
C3—C4	1.510 (4)	C16—C17	1.387 (4)
C3—C15	1.524 (4)	C17—C18	1.370 (4)
C3—H3	0.9800	C17—H17	0.9300
C4—C13	1.335 (4)	C18—C19	1.373 (4)
C4—C5	1.470 (4)	C18—H18	0.9300
C5—C6	1.487 (4)	C19—C20	1.383 (4)
C6—C7	1.380 (4)	C19—H19	0.9300
C6—C11	1.396 (4)	C20—H20	0.9300
C13—O1—C1	117.4 (2)	C8—C9—H9	119.7
C1—N1—H1A	120.0	C9—C10—C11	120.0 (3)
C1—N1—H1B	120.0	C9—C10—H10	120.0
H1A—N1—H1B	120.0	C11—C10—H10	120.0
N1—C1—C2	127.8 (3)	C10—C11—C6	119.6 (3)
N1—C1—O1	110.1 (3)	C10—C11—C12	120.2 (3)
C2—C1—O1	122.1 (3)	C6—C11—C12	120.2 (3)
C1—C2—C14	120.4 (3)	O3—C12—C11	122.6 (3)
C1—C2—C3	122.9 (3)	O3—C12—C13	120.7 (3)
C14—C2—C3	116.6 (3)	C11—C12—C13	116.8 (3)
C4—C3—C2	108.4 (2)	C4—C13—O1	124.6 (3)
C4—C3—C15	114.8 (2)	C4—C13—C12	123.5 (3)
C2—C3—C15	113.2 (3)	O1—C13—C12	111.9 (3)
C4—C3—H3	106.6	N2—C14—C2	177.6 (4)
C2—C3—H3	106.6	C16—C15—C20	116.6 (3)
C15—C3—H3	106.6	C16—C15—C3	125.4 (3)
C13—C4—C5	120.3 (3)	C20—C15—C3	118.0 (3)
C13—C4—C3	121.8 (3)	C15—C16—C17	122.3 (3)
C5—C4—C3	117.8 (3)	C15—C16—Cl1	120.9 (2)
O2—C5—C4	119.6 (3)	C17—C16—Cl1	116.8 (3)
O2—C5—C6	121.8 (3)	C18—C17—C16	119.4 (3)
C4—C5—C6	118.6 (3)	C18—C17—H17	120.3
C7—C6—C11	119.7 (3)	C16—C17—H17	120.3
C7—C6—C5	119.8 (3)	C17—C18—C19	120.1 (3)
C11—C6—C5	120.6 (3)	C17—C18—H18	120.0
C8—C7—C6	120.2 (3)	C19—C18—H18	120.0
C8—C7—H7	119.9	C18—C19—C20	119.9 (3)
C6—C7—H7	119.9	C18—C19—H19	120.0
C9—C8—C7	120.0 (4)	C20—C19—H19	120.0
C9—C8—H8	120.0	C19—C20—C15	121.6 (3)
C7—C8—H8	120.0	C19—C20—H20	119.2
C10—C9—C8	120.5 (4)	C15—C20—H20	119.2
C10—C9—H9	119.7
C13—O1—C1—N1	174.8 (2)	C7—C6—C11—C12	−178.1 (3)
C13—O1—C1—C2	−3.9 (4)	C5—C6—C11—C12	2.1 (4)
N1—C1—C2—C14	−5.9 (6)	C10—C11—C12—O3	−1.4 (5)
O1—C1—C2—C14	172.6 (3)	C6—C11—C12—O3	177.0 (3)
N1—C1—C2—C3	169.9 (3)	C10—C11—C12—C13	179.9 (3)
O1—C1—C2—C3	−11.5 (5)	C6—C11—C12—C13	−1.7 (4)
C1—C2—C3—C4	18.2 (4)	C5—C4—C13—O1	−179.1 (3)
C14—C2—C3—C4	−165.8 (3)	C3—C4—C13—O1	−2.0 (5)
C1—C2—C3—C15	−110.3 (4)	C5—C4—C13—C12	2.0 (5)
C14—C2—C3—C15	65.6 (4)	C3—C4—C13—C12	179.1 (3)
C2—C3—C4—C13	−11.5 (4)	C1—O1—C13—C4	11.0 (4)
C15—C3—C4—C13	116.1 (3)	C1—O1—C13—C12	−170.1 (3)
C2—C3—C4—C5	165.6 (3)	O3—C12—C13—C4	−179.1 (3)
C15—C3—C4—C5	−66.7 (3)	C11—C12—C13—C4	−0.4 (4)
C13—C4—C5—O2	178.4 (3)	O3—C12—C13—O1	1.9 (4)
C3—C4—C5—O2	1.1 (4)	C11—C12—C13—O1	−179.4 (2)
C13—C4—C5—C6	−1.6 (4)	C4—C3—C15—C16	−57.8 (4)
C3—C4—C5—C6	−178.8 (3)	C2—C3—C15—C16	67.4 (4)
O2—C5—C6—C7	−0.2 (5)	C4—C3—C15—C20	124.2 (3)
C4—C5—C6—C7	179.7 (3)	C2—C3—C15—C20	−110.6 (3)
O2—C5—C6—C11	179.5 (3)	C20—C15—C16—C17	−1.4 (5)
C4—C5—C6—C11	−0.6 (4)	C3—C15—C16—C17	−179.4 (3)
C11—C6—C7—C8	0.7 (5)	C20—C15—C16—Cl1	178.3 (2)
C5—C6—C7—C8	−179.5 (3)	C3—C15—C16—Cl1	0.2 (4)
C6—C7—C8—C9	−1.4 (5)	C15—C16—C17—C18	0.8 (5)
C7—C8—C9—C10	1.1 (5)	Cl1—C16—C17—C18	−178.8 (3)
C8—C9—C10—C11	−0.1 (5)	C16—C17—C18—C19	0.4 (5)
C9—C10—C11—C6	−0.6 (5)	C17—C18—C19—C20	−1.0 (5)
C9—C10—C11—C12	177.8 (3)	C18—C19—C20—C15	0.4 (5)
C7—C6—C11—C10	0.3 (5)	C16—C15—C20—C19	0.8 (5)
C5—C6—C11—C10	−179.5 (3)	C3—C15—C20—C19	179.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2i	0.86	2.26	3.080 (4)	159
N1—H1B···O3ii	0.86	2.22	2.889 (3)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N2i	0.86	2.26	3.080 (4)	159
N1—H1B⋯O3ii	0.86	2.22	2.889 (3)	134

Symmetry codes: (i) ; (ii) .