Ethyl 2-amino-4-(3-chloro­phen­yl)-5,10-dioxo-5,10-dihydro-4H-benzo[g]chromene-3-carboxyl­ate

Hu, X.; Lei, S.; Yao, C.-S.

doi:10.1107/S160053680901753X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1324

doi:10.1107/S160053680901753X

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Ethyl 2-amino-4-(3-chlorophenyl)-5,10-dioxo-5,10-dihydro-4H-benzo[g]chromene-3-carboxylate

Xiao Hu,^a ^* Song Lei ^b,^c and Chang-Sheng Yao ^b,^c

^aXuzhou Ruisai Technology Industry Co. Ltd, Xuzhou 221004, People's Republic of China, ^bDepartment of Chemistry, Xuzhou Normal University, Xuzhou 221116, People's Republic of China, and ^cKey Laboratory of Biotechnology for Medical Plants of Jiangsu Province, Xuzhou 221116, People's Republic of China
^*Correspondence e-mail: chshengyaonk@mail.nankai.edu.cn

(Received 4 May 2009; accepted 11 May 2009; online 20 May 2009)

The title molecule, C₂₂H₁₆ClNO₅, was obtained by the reaction of (E)-ethyl 3-(3-chlorophenyl)-2-cyanoacrylate and 2-hydroxynaphthalene-1,4-dione catalysed by triethylamine in ethanol. In the crystal structure, the chlorobenzene ring makes a dihedral angle of 88.63 (4)° with the fused ring system. The six-membered ring formed by an intramolecular N—H⋯O hydrogen bond is almost planar. The crystal packing is stabilized by N—H⋯O hydrogen bonds.

Related literature

For the antitumor activity of 4H-naphtho[2,3-b]pyran-5,10-dione derivatives, see: Fujimoto (2007 ); Perchellet et al. (2001 ); Zhan et al. (2007 ). For natural products containing H-naphtho[2,3-b]pyran-5,10-dione, see: Jassbi et al. (2004 ); Rodriguez et al. (2003 ).

Experimental

Crystal data

C₂₂H₁₆ClNO₅
M_r = 409.81
Triclinic, $[P \overline 1]$
a = 6.1175 (17) Å
b = 10.021 (3) Å
c = 15.967 (5) Å
α = 84.840 (13)°
β = 87.714 (12)°
γ = 67.429 (8)°
V = 900.2 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 113 K
0.32 × 0.30 × 0.20 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (Jacobson, 1998 ) T_min = 0.924, T_max = 0.952
11338 measured reflections
4261 independent reflections
3031 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.097
S = 1.01
4261 reflections
272 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4	0.898 (18)	2.049 (18)	2.6827 (17)	126.5 (15)
N1—H2⋯O2ⁱ	0.880 (19)	2.12 (2)	2.9913 (17)	170.2 (18)
Symmetry code: (i) -x+2, -y, -z.

Data collection: CrystalClear (Rigaku/MSC, 2002 ); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680901753X/hg2512sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680901753X/hg2512Isup2.hkl

checkCIF report

Comment top

The derivatives of 4H-naphtho[2,3-b]pyran-5,10-dione have antitumor activities (Fujimoto, 2007; Zhan et al., 2007; Perchellet et al., 2001). Besides, some natural products also contain this moiety (Rodriguez et al., 2003; Jassbi et al., 2004). In order to develop new potential antitumor chemicals, a series of novel 4H-naphtho[2,3-b]pyran-5,10-dione derivatives based on the scaffolds of natural products have been synthesized. However, to the best of our knowledge, there are no reports on the crystal structure of these compounds. Determination of the molecular structure is crucial to the study of the structure and activity relationship. Here we report the crystal structure of the title compound, (I).

The molecular structure of (I) is shown in Fig. 1. It consists of five rings, considering the six-membered ring formed by the intramolecular N1—H1···O4 hydrogen bond (Table 1). The dihedral angles between the neighbouring rings show that the naphthalene ring and the pyran ring in an envelope conformation are almost coplanar. The phenyl ring bonded to the pyrans ring is almost perpendicular to the fused ring, for the dihedral angle is 88.63 (4)°. In the molecular structure, the crystal packing is stabilized N1—H2···O2 intermolecular hydrogen bonds. (Figs.2, Table 1)

Related literature top

For the antitumor activity of 4H-naphtho[2,3-b]pyran-5,10-dione derivatives, see: Fujimoto (2007); Perchellet et al. (2001); Zhan et al. (2007). For natural products conatianing H-naphtho[2,3-b]pyran-5,10-dione, see: Jassbi et al. (2004); Rodriguez et al. (2003).

Experimental top

The title compound was synthesized by the reaction of (E)-ethyl 3-(3-chlorophenyl)-2-cyanoacrylate (1 mmol) and 2-hydroxynaphthalene-1,4-dione (1 mmol) catalyzed by Et₃N in 15 ml ethanol at reluxing temperature. After cooling, the solvent was removed at reduced pressure and the residue was washed with water and recrystallized from ethanol, which gave single crystals suitable for X-ray diffraction.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2002); cell refinement: CrystalClear (Rigaku/MSC, 2002); data reduction: CrystalClear (Rigaku/MSC, 2002); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The packing diagram of (I). Intermolecular hydrogen bonds are shown as dashed lines.

Ethyl 2-amino-4-(3-chlorophenyl)-5,10-dioxo-5,10-dihydro- 4H-benzo[g]chromene-3-carboxylate top

Crystal data top

C₂₂H₁₆ClNO₅	Z = 2
M_r = 409.81	F(000) = 424
Triclinic, P1	D_x = 1.512 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71070 Å
a = 6.1175 (17) Å	Cell parameters from 2873 reflections
b = 10.021 (3) Å	θ = 2.2–27.9°
c = 15.967 (5) Å	µ = 0.25 mm⁻¹
α = 84.840 (13)°	T = 113 K
β = 87.714 (12)°	Block, red
γ = 67.429 (8)°	0.32 × 0.30 × 0.20 mm
V = 900.2 (4) Å³

Data collection top

Rigaku Saturn diffractometer	4261 independent reflections
Radiation source: rotating anode	3031 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.033
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 2.2°
ω scans	h = −8→8
Absorption correction: multi-scan (Jacobson, 1998)	k = −13→13
T_min = 0.924, T_max = 0.952	l = −20→20
11338 measured reflections

Refinement top

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)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.097	w = 1/[σ²(F_o²) + (0.0583P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
4261 reflections	Δρ_max = 0.37 e Å⁻³
272 parameters	Δρ_min = −0.45 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: 0.020 (4)

Crystal data top

C₂₂H₁₆ClNO₅	γ = 67.429 (8)°
M_r = 409.81	V = 900.2 (4) Å³
Triclinic, P1	Z = 2
a = 6.1175 (17) Å	Mo Kα radiation
b = 10.021 (3) Å	µ = 0.25 mm⁻¹
c = 15.967 (5) Å	T = 113 K
α = 84.840 (13)°	0.32 × 0.30 × 0.20 mm
β = 87.714 (12)°

Data collection top

Rigaku Saturn diffractometer	4261 independent reflections
Absorption correction: multi-scan (Jacobson, 1998)	3031 reflections with I > 2σ(I)
T_min = 0.924, T_max = 0.952	R_int = 0.033
11338 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.37 e Å⁻³
4261 reflections	Δρ_min = −0.45 e Å⁻³
272 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	0.49377 (7)	0.57379 (4)	0.30597 (2)	0.02735 (12)
O1	−0.07224 (16)	0.26225 (11)	0.15817 (6)	0.0199 (2)
O2	0.68318 (17)	0.12419 (11)	−0.04552 (6)	0.0231 (2)
O3	0.75549 (16)	0.04439 (10)	0.11440 (5)	0.0172 (2)
O4	0.88099 (17)	−0.17355 (11)	0.35482 (6)	0.0225 (2)
O5	0.48890 (16)	−0.07946 (10)	0.38009 (6)	0.0184 (2)
N1	1.0294 (2)	−0.10163 (13)	0.20348 (8)	0.0191 (3)
C1	0.0990 (2)	0.23745 (14)	0.11164 (8)	0.0156 (3)
C2	0.0730 (2)	0.29181 (14)	0.02047 (8)	0.0162 (3)
C3	−0.1499 (2)	0.37702 (15)	−0.01112 (8)	0.0194 (3)
H3	−0.2854	0.3985	0.0244	0.023*
C4	−0.1737 (3)	0.43104 (16)	−0.09541 (9)	0.0223 (3)
H4	−0.3264	0.4885	−0.1173	0.027*
C5	0.0222 (3)	0.40187 (16)	−0.14729 (9)	0.0228 (3)
H5	0.0044	0.4412	−0.2042	0.027*
C6	0.2449 (3)	0.31522 (15)	−0.11653 (8)	0.0203 (3)
H6	0.3795	0.2939	−0.1524	0.024*
C7	0.2707 (2)	0.25930 (14)	−0.03244 (8)	0.0167 (3)
C8	0.5078 (2)	0.16626 (14)	−0.00028 (8)	0.0164 (3)
C9	0.5273 (2)	0.12298 (14)	0.09172 (8)	0.0155 (3)
C10	0.3409 (2)	0.15414 (14)	0.14472 (8)	0.0147 (3)
C11	0.3707 (2)	0.10501 (14)	0.23718 (8)	0.0148 (3)
H11	0.2601	0.0547	0.2528	0.018*
C12	0.6221 (2)	−0.00336 (14)	0.25298 (8)	0.0155 (3)
C13	0.7982 (2)	−0.02151 (14)	0.19472 (8)	0.0157 (3)
C14	0.3041 (2)	0.23611 (14)	0.28925 (8)	0.0145 (3)
C15	0.4265 (2)	0.32887 (14)	0.27878 (8)	0.0155 (3)
H15	0.5580	0.3086	0.2414	0.019*
C16	0.3534 (2)	0.45117 (15)	0.32365 (8)	0.0191 (3)
C17	0.1670 (3)	0.48205 (16)	0.38070 (8)	0.0233 (3)
H17	0.1203	0.5659	0.4111	0.028*
C18	0.0507 (3)	0.38732 (16)	0.39210 (9)	0.0238 (3)
H18	−0.0756	0.4055	0.4316	0.029*
C19	0.1165 (2)	0.26597 (16)	0.34642 (8)	0.0203 (3)
H19	0.0329	0.2030	0.3542	0.024*
C20	0.6813 (2)	−0.09205 (14)	0.33211 (8)	0.0163 (3)
C21	0.5361 (2)	−0.17302 (15)	0.45788 (8)	0.0199 (3)
H21A	0.6348	−0.1461	0.4955	0.024*
H21B	0.6222	−0.2754	0.4458	0.024*
C22	0.3031 (3)	−0.15439 (17)	0.49923 (9)	0.0251 (3)
H22A	0.3301	−0.2167	0.5518	0.030*
H22B	0.2069	−0.1814	0.4616	0.030*
H22C	0.2199	−0.0529	0.5113	0.030*
H1	1.081 (3)	−0.160 (2)	0.2506 (12)	0.037 (5)*
H2	1.111 (3)	−0.118 (2)	0.1561 (12)	0.044 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0303 (2)	0.01992 (19)	0.0328 (2)	−0.00981 (15)	−0.00537 (15)	−0.00406 (15)
O1	0.0141 (5)	0.0219 (5)	0.0218 (5)	−0.0057 (4)	0.0003 (4)	0.0018 (4)
O2	0.0216 (5)	0.0269 (6)	0.0188 (5)	−0.0069 (4)	0.0051 (4)	−0.0046 (4)
O3	0.0142 (5)	0.0194 (5)	0.0159 (5)	−0.0043 (4)	0.0011 (4)	−0.0011 (4)
O4	0.0178 (5)	0.0202 (5)	0.0229 (5)	−0.0005 (4)	−0.0025 (4)	0.0027 (4)
O5	0.0171 (5)	0.0179 (5)	0.0163 (5)	−0.0037 (4)	−0.0009 (4)	0.0048 (4)
N1	0.0145 (6)	0.0204 (6)	0.0194 (6)	−0.0033 (5)	0.0018 (5)	−0.0030 (5)
C1	0.0169 (7)	0.0139 (6)	0.0175 (6)	−0.0076 (5)	−0.0007 (5)	−0.0012 (5)
C2	0.0184 (7)	0.0141 (6)	0.0174 (7)	−0.0075 (5)	−0.0018 (5)	−0.0013 (5)
C3	0.0194 (7)	0.0183 (7)	0.0215 (7)	−0.0082 (6)	−0.0015 (5)	−0.0010 (6)
C4	0.0229 (7)	0.0205 (7)	0.0227 (7)	−0.0072 (6)	−0.0077 (6)	0.0006 (6)
C5	0.0305 (8)	0.0221 (7)	0.0168 (7)	−0.0110 (6)	−0.0037 (6)	0.0003 (6)
C6	0.0247 (8)	0.0211 (7)	0.0162 (7)	−0.0099 (6)	0.0006 (5)	−0.0020 (6)
C7	0.0207 (7)	0.0147 (6)	0.0168 (6)	−0.0086 (5)	−0.0009 (5)	−0.0029 (5)
C8	0.0197 (7)	0.0151 (6)	0.0171 (6)	−0.0090 (5)	0.0018 (5)	−0.0043 (5)
C9	0.0161 (7)	0.0137 (6)	0.0170 (6)	−0.0058 (5)	−0.0007 (5)	−0.0025 (5)
C10	0.0166 (7)	0.0125 (6)	0.0156 (6)	−0.0062 (5)	−0.0001 (5)	−0.0012 (5)
C11	0.0147 (6)	0.0144 (6)	0.0148 (6)	−0.0056 (5)	−0.0005 (5)	0.0015 (5)
C12	0.0145 (6)	0.0135 (6)	0.0172 (6)	−0.0036 (5)	−0.0005 (5)	−0.0015 (5)
C13	0.0169 (7)	0.0128 (6)	0.0175 (6)	−0.0056 (5)	−0.0024 (5)	−0.0021 (5)
C14	0.0132 (6)	0.0136 (6)	0.0121 (6)	−0.0004 (5)	−0.0020 (5)	0.0016 (5)
C15	0.0140 (6)	0.0165 (7)	0.0123 (6)	−0.0019 (5)	−0.0005 (5)	0.0003 (5)
C16	0.0217 (7)	0.0163 (7)	0.0163 (6)	−0.0040 (6)	−0.0060 (5)	0.0015 (5)
C17	0.0261 (8)	0.0181 (7)	0.0157 (7)	0.0032 (6)	−0.0041 (5)	−0.0027 (5)
C18	0.0205 (7)	0.0248 (8)	0.0155 (7)	0.0020 (6)	0.0035 (5)	0.0005 (6)
C19	0.0181 (7)	0.0217 (7)	0.0172 (7)	−0.0042 (6)	0.0005 (5)	0.0031 (5)
C20	0.0162 (7)	0.0125 (6)	0.0186 (7)	−0.0034 (5)	−0.0002 (5)	−0.0027 (5)
C21	0.0222 (7)	0.0181 (7)	0.0152 (6)	−0.0042 (6)	−0.0033 (5)	0.0047 (5)
C22	0.0244 (8)	0.0299 (8)	0.0195 (7)	−0.0102 (6)	−0.0016 (6)	0.0058 (6)

Geometric parameters (Å, º) top

Cl1—C16	1.7479 (15)	C8—C9	1.4899 (18)
O1—C1	1.2177 (16)	C9—C10	1.3457 (18)
O2—C8	1.2231 (16)	C10—C11	1.5089 (17)
O3—C9	1.3584 (16)	C11—C12	1.5194 (18)
O3—C13	1.3751 (15)	C11—C14	1.5303 (19)
O4—C20	1.2274 (16)	C11—H11	1.0000
O5—C20	1.3492 (16)	C12—C13	1.3635 (18)
O5—C21	1.4549 (15)	C12—C20	1.4508 (18)
N1—C13	1.3372 (17)	C14—C19	1.3938 (18)
N1—H1	0.898 (18)	C14—C15	1.3959 (19)
N1—H2	0.880 (19)	C15—C16	1.3881 (19)
C1—C10	1.4834 (18)	C15—H15	0.9500
C1—C2	1.5002 (18)	C16—C17	1.387 (2)
C2—C3	1.3879 (19)	C17—C18	1.384 (2)
C2—C7	1.3959 (19)	C17—H17	0.9500
C3—C4	1.3963 (19)	C18—C19	1.390 (2)
C3—H3	0.9500	C18—H18	0.9500
C4—C5	1.379 (2)	C19—H19	0.9500
C4—H4	0.9500	C21—C22	1.498 (2)
C5—C6	1.386 (2)	C21—H21A	0.9900
C5—H5	0.9500	C21—H21B	0.9900
C6—C7	1.3984 (18)	C22—H22A	0.9800
C6—H6	0.9500	C22—H22B	0.9800
C7—C8	1.4739 (19)	C22—H22C	0.9800

C9—O3—C13	118.10 (10)	C14—C11—H11	108.1
C20—O5—C21	115.05 (10)	C13—C12—C20	117.77 (11)
C13—N1—H1	119.2 (11)	C13—C12—C11	122.20 (11)
C13—N1—H2	115.0 (12)	C20—C12—C11	120.02 (11)
H1—N1—H2	121.7 (17)	N1—C13—C12	128.18 (12)
O1—C1—C10	120.28 (11)	N1—C13—O3	109.49 (11)
O1—C1—C2	121.46 (11)	C12—C13—O3	122.33 (11)
C10—C1—C2	118.25 (11)	C19—C14—C15	119.25 (12)
C3—C2—C7	119.80 (12)	C19—C14—C11	120.14 (12)
C3—C2—C1	119.51 (12)	C15—C14—C11	120.59 (11)
C7—C2—C1	120.68 (11)	C16—C15—C14	119.13 (12)
C2—C3—C4	119.58 (13)	C16—C15—H15	120.4
C2—C3—H3	120.2	C14—C15—H15	120.4
C4—C3—H3	120.2	C17—C16—C15	122.12 (14)
C5—C4—C3	120.69 (13)	C17—C16—Cl1	118.47 (11)
C5—C4—H4	119.7	C15—C16—Cl1	119.39 (11)
C3—C4—H4	119.7	C18—C17—C16	118.20 (13)
C4—C5—C6	120.06 (13)	C18—C17—H17	120.9
C4—C5—H5	120.0	C16—C17—H17	120.9
C6—C5—H5	120.0	C17—C18—C19	120.85 (13)
C5—C6—C7	119.77 (13)	C17—C18—H18	119.6
C5—C6—H6	120.1	C19—C18—H18	119.6
C7—C6—H6	120.1	C18—C19—C14	120.40 (14)
C2—C7—C6	120.06 (12)	C18—C19—H19	119.8
C2—C7—C8	120.43 (12)	C14—C19—H19	119.8
C6—C7—C8	119.50 (12)	O4—C20—O5	121.56 (12)
O2—C8—C7	122.97 (12)	O4—C20—C12	125.79 (12)
O2—C8—C9	120.19 (12)	O5—C20—C12	112.64 (11)
C7—C8—C9	116.84 (11)	O5—C21—C22	107.88 (11)
C10—C9—O3	124.60 (12)	O5—C21—H21A	110.1
C10—C9—C8	124.01 (12)	C22—C21—H21A	110.1
O3—C9—C8	111.36 (11)	O5—C21—H21B	110.1
C9—C10—C1	119.43 (11)	C22—C21—H21B	110.1
C9—C10—C11	121.75 (12)	H21A—C21—H21B	108.4
C1—C10—C11	118.82 (11)	C21—C22—H22A	109.5
C10—C11—C12	109.30 (10)	C21—C22—H22B	109.5
C10—C11—C14	110.13 (10)	H22A—C22—H22B	109.5
C12—C11—C14	112.83 (11)	C21—C22—H22C	109.5
C10—C11—H11	108.1	H22A—C22—H22C	109.5
C12—C11—H11	108.1	H22B—C22—H22C	109.5

O1—C1—C2—C3	2.5 (2)	C1—C10—C11—C12	168.17 (11)
C10—C1—C2—C3	−176.36 (12)	C9—C10—C11—C14	113.41 (14)
O1—C1—C2—C7	−178.39 (13)	C1—C10—C11—C14	−67.34 (15)
C10—C1—C2—C7	2.70 (19)	C10—C11—C12—C13	14.24 (18)
C7—C2—C3—C4	−0.8 (2)	C14—C11—C12—C13	−108.66 (14)
C1—C2—C3—C4	178.23 (12)	C10—C11—C12—C20	−165.61 (11)
C2—C3—C4—C5	−0.7 (2)	C14—C11—C12—C20	71.50 (15)
C3—C4—C5—C6	1.6 (2)	C20—C12—C13—N1	−7.3 (2)
C4—C5—C6—C7	−1.0 (2)	C11—C12—C13—N1	172.81 (13)
C3—C2—C7—C6	1.5 (2)	C20—C12—C13—O3	172.24 (11)
C1—C2—C7—C6	−177.59 (12)	C11—C12—C13—O3	−7.6 (2)
C3—C2—C7—C8	−178.63 (12)	C9—O3—C13—N1	175.65 (11)
C1—C2—C7—C8	2.31 (19)	C9—O3—C13—C12	−4.00 (18)
C5—C6—C7—C2	−0.6 (2)	C10—C11—C14—C19	118.09 (13)
C5—C6—C7—C8	179.53 (13)	C12—C11—C14—C19	−119.49 (13)
C2—C7—C8—O2	173.40 (13)	C10—C11—C14—C15	−60.43 (15)
C6—C7—C8—O2	−6.7 (2)	C12—C11—C14—C15	62.00 (15)
C2—C7—C8—C9	−6.16 (18)	C19—C14—C15—C16	−2.01 (18)
C6—C7—C8—C9	173.74 (12)	C11—C14—C15—C16	176.52 (11)
C13—O3—C9—C10	7.43 (19)	C14—C15—C16—C17	2.07 (19)
C13—O3—C9—C8	−170.55 (10)	C14—C15—C16—Cl1	−176.00 (9)
O2—C8—C9—C10	−174.20 (13)	C15—C16—C17—C18	−0.47 (19)
C7—C8—C9—C10	5.37 (19)	Cl1—C16—C17—C18	177.61 (10)
O2—C8—C9—O3	3.80 (18)	C16—C17—C18—C19	−1.2 (2)
C7—C8—C9—O3	−176.63 (11)	C17—C18—C19—C14	1.2 (2)
O3—C9—C10—C1	−178.19 (12)	C15—C14—C19—C18	0.43 (19)
C8—C9—C10—C1	−0.5 (2)	C11—C14—C19—C18	−178.10 (12)
O3—C9—C10—C11	1.1 (2)	C21—O5—C20—O4	−2.29 (19)
C8—C9—C10—C11	178.79 (12)	C21—O5—C20—C12	176.26 (11)
O1—C1—C10—C9	177.45 (12)	C13—C12—C20—O4	6.9 (2)
C2—C1—C10—C9	−3.64 (19)	C11—C12—C20—O4	−173.26 (13)
O1—C1—C10—C11	−1.82 (19)	C13—C12—C20—O5	−171.59 (12)
C2—C1—C10—C11	177.09 (11)	C11—C12—C20—O5	8.26 (17)
C9—C10—C11—C12	−11.08 (17)	C20—O5—C21—C22	−175.25 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.898 (18)	2.049 (18)	2.6827 (17)	126.5 (15)
N1—H2···O2ⁱ	0.880 (19)	2.12 (2)	2.9913 (17)	170.2 (18)

Symmetry code: (i) −x+2, −y, −z.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₆ClNO₅
M_r	409.81
Crystal system, space group	Triclinic, P1
Temperature (K)	113
a, b, c (Å)	6.1175 (17), 10.021 (3), 15.967 (5)
α, β, γ (°)	84.840 (13), 87.714 (12), 67.429 (8)
V (Å³)	900.2 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.32 × 0.30 × 0.20

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (Jacobson, 1998)
T_min, T_max	0.924, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	11338, 4261, 3031
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.097, 1.01
No. of reflections	4261
No. of parameters	272
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.45

Computer programs: CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.898 (18)	2.049 (18)	2.6827 (17)	126.5 (15)
N1—H2···O2ⁱ	0.880 (19)	2.12 (2)	2.9913 (17)	170.2 (18)

Symmetry code: (i) −x+2, −y, −z.

References

Fujimoto, S. (2007). Biol. Pharm. Bull. 30, 1923–1929. Web of Science CrossRef PubMed CAS Google Scholar
Jacobson, R. (1998). Private communication to the Rigaku Corporation, Tokyo, Japan. Google Scholar
Jassbi, A. R., Singh, P., Jain, S. & Tahara, S. (2004). Helv. Chim. Acta, 87, 820–824. Web of Science CrossRef CAS Google Scholar
Perchellet, E. M., Sperfslage, B. J., Qabaja, G., Jones, G. B. & Perchellet, J.-P. (2001). Anti-Cancer Drugs, 12, 401–417. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Rodriguez, J. C., Fernandez Puentes, J. L., Baz, J. P. & Canedo, L. M. (2003). J. Antibiot. 56, 318–321. Web of Science PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhan, J. X., Burns, A. M., Liu, M. P. X., Faeth, S. H. & Gunatilaka, A. A. L. (2007). J. Nat. Prod. 70, 227–232. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 65| Part 6| June 2009| Page o1324

doi:10.1107/S160053680901753X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl 2-amino-4-(3-chloro­phen­yl)-5,10-dioxo-5,10-di­hydro-4H-benzo[g]chromene-3-carboxyl­ate

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Experimental

Crystal data

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Refinement

Supporting information

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organic compounds

Ethyl 2-amino-4-(3-chlorophenyl)-5,10-dioxo-5,10-dihydro-4H-benzo[g]chromene-3-carboxylate