2-Amino-4-(2-chloro­phen­yl)-5,10-dioxo-5,10-dihydro-4H-benzo[g]chromene-3-carbonitrile

Zhang, J.; Zhang, X.; Yan, S.; Ma, N.; Tu, S.

doi:10.1107/S1600536808039986

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o5

doi:10.1107/S1600536808039986

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2-Amino-4-(2-chlorophenyl)-5,10-dioxo-5,10-dihydro-4H-benzo[g]chromene-3-carbonitrile

Jinpeng Zhang,^a Xiaohong Zhang,^b Shu Yan,^b Ning Ma ^b and Shujiang Tu ^b ^*

^aDepartment of Public Health, Xuzhou Medical College, Xuzhou 221000, People's Republic of China, and ^bSchool of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou 221116, People's Republic of China
^*Correspondence e-mail: laotu2001@263.net

(Received 24 November 2008; accepted 27 November 2008; online 3 December 2008)

In the molecule of the title compound, C₂₀H₁₁ClN₂O₃, the pyran ring adopts a flattened-boat conformation. In the crystal structure, intermolecular N—H⋯N and N—H⋯O hydrogen bonds generate edge-fused R₂²(12) and R₂²(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 chlorophenyl 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_r = 362.76
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.053
wR(F²) = 0.100
S = 1.04
2746 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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) -x, -y+1, -z+2; (ii) -x, -y+1, -z+1.

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.

Supporting information

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

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

checkCIF report

Comment top

Pyrans and their derivatives are important compounds, which are found to possess antibacterial (El-Agrody et al., 2000) and antitumor (Mohr et al., 1975) activities and antiallergic (Banzatti et al., 1984; Hatakeyama et al., 1988) and hypotensive (Tandon et al., 1991) effects. Compounds of 1,4-naphthoquinone series possess potent and versatile biological activities, such as antiallergic and anticancer activities (Kongkathip et al., 2003). For these reasons, 1,4-pyranonaphthoquinone derivatives possessing both pyran ring and 1,4-naphthoquinone motif are strongly desired. We report herein the crystal structure of the title compound.

In the molecule of the title compound (Fig. 1) the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings B (C4-C6/C11-C13), C (C6-C11) and D (C15-C20) are, of course, planar and the dihedral angles between them are B/C = 1.33 (3)°, B/D = 83.55 (3)° and C/D = 82.65 (3)°. So, rings B and C are nearly coplanar. Ring A (O1/C1-C4/C13) is not planar, having total puckering amplitude, Q_T, of 0.172 (3) and flattened-boat conformation [ϕ = -22.99 (3)° and θ = 105.077 (4)°] (Cremer & Pople, 1975).

In the crystal structure, intermolecular N-H···N and N-H···O hydrogen bonds (Table 1) generate edge-fused R₂²(12) and R₂²(14) ring motifs (Fig. 2) (Bernstein et al., 1995). The hydrogen bonded motifs are linked to each other to form a three dimensional network, in which they may be effective in the stabilization of the structure. The π-π contact between the chlorophenyl rings, Cg4—Cg4ⁱ [symmetry code: (i) -x, -y, 2 - z, where Cg4 is centroid of the ring D (C15-C20)] may further stabilize the structure, with centroid-centroid distance of 3.879 (3) Å.

Related literature top

For general background, 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 top

The title compound was prepared by the reaction of 2-(2-chlorobenzylidene)- malononitrile (1 mmol) and 2-hydroxynaphthalene-1,4-dione (1 mmol) in glacial acetic acid without catalyst. Crystals suitable for X-ray analysis were obtained by slow evaporation of an aqueous ethanol solution (95%) (yield; 90%; m.p. > 573 K).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

2-Amino-4-(2-chlorophenyl)-5,10-dioxo-5,10-dihydro-4H- benzo[g]chromene-3-carbonitrile top

Crystal data top

C₂₀H₁₁ClN₂O₃	Z = 2
M_r = 362.76	F(000) = 372
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0295P)²] where P = (F_o² + 2F_c²)/3
2746 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₀H₁₁ClN₂O₃	γ = 110.732 (2)°
M_r = 362.76	V = 793.95 (18) Å³
Triclinic, P1	Z = 2
a = 8.3201 (10) Å	Mo Kα radiation
b = 9.3729 (12) Å	µ = 0.27 mm⁻¹
c = 11.0081 (16) Å	T = 298 K
α = 93.015 (1)°	0.17 × 0.15 × 0.10 mm
β = 96.393 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2746 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1566 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.974	R_int = 0.025
4207 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.04	Δρ_max = 0.40 e Å⁻³
2746 reflections	Δρ_min = −0.26 e Å⁻³
235 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y+1, −z+2; (ii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₁ClN₂O₃
M_r	362.76
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.3201 (10), 9.3729 (12), 11.0081 (16)
α, β, γ (°)	93.015 (1), 96.393 (1), 110.732 (2)
V (Å³)	793.95 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.17 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.956, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	4207, 2746, 1566
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.100, 1.04
No. of reflections	2746
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.26

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2ⁱ	0.86	2.26	3.080 (4)	159.2
N1—H1B···O3ⁱⁱ	0.86	2.22	2.889 (3)	133.9

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

Acknowledgements

We thank the National Natural Science Foundation of China (grant No. 20672090), the Natural Science Foundation of Jiangsu Province (grant No. BK2006033) and the Foundation of Xuzhou Medical College (grant No. 08KJ50) for support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-Amino-4-(2-chloro­phen­yl)-5,10-dioxo-5,10-di­hydro-4H-benzo[g]chromene-3-carbo­nitrile

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-Amino-4-(2-chlorophenyl)-5,10-dioxo-5,10-dihydro-4H-benzo[g]chromene-3-carbonitrile