2-Meth­oxy-3-[(3,4,5-trimethoxy­anilino)methyl­idene]-3,4-dihydro-2H-1-benzopyran-4-one

Małecka, M.; Ciołkowski, M.; Budzisz, E.

doi:10.1107/S1600536809054889

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o246

doi:10.1107/S1600536809054889

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2-Methoxy-3-[(3,4,5-trimethoxyanilino)methylidene]-3,4-dihydro-2H-1-benzopyran-4-one

Magdalena Małecka,^a Michał Ciołkowski ^b and Elżbieta Budzisz ^b ^*

^aDepartment of Crystallography and Crystal Chemistry, University of Łódź, Pomorska 149/153, PL-90236 Łódź, Poland, and ^bDepartment of Cosmetic Raw Materials Chemistry, Faculty of Pharmacy, Medical University of Łódź, Muszyńskiego 1, PL-90151 Łódź, Poland
^*Correspondence e-mail: malecka@uni.lodz.pl

(Received 9 December 2009; accepted 21 December 2009; online 24 December 2009)

The title molecule, C₂₀H₂₁NO₆, adopts a keto–amine tautomeric form. An intramolecular N—H⋯O hydrogen bond, classified as a resonanse-assisted hydrogen bond, influences the molecular conformation; the two benzene rings form a dihedral angle of 24.6 (1)°. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds link molecules into chains propagating along [001].

Related literature

For the biological propertries of similar structures, see: Khan et al. (2009 ). For related structures, see: Gilli et al. (1994 ); Bertolasi et al. (1998 ); Małecka & Budzisz (2006 ); Małecka (2007 ).

Experimental

Crystal data

C₂₀H₂₁NO₆
M_r = 371.38
Monoclinic, P 2₁ /c
a = 11.6145 (6) Å
b = 20.8689 (9) Å
c = 7.3728 (5) Å
β = 94.533 (5)°
V = 1781.44 (17) Å³
Z = 4
Cu Kα radiation
μ = 0.86 mm⁻¹
T = 100 K
0.2 × 0.05 × 0.03 mm

Data collection

Oxford Diffraction Gemini E Ultra diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.844, T_max = 1.000
7511 measured reflections
2862 independent reflections
2344 reflections with I > 2σ(I)
R_int = 0.024
Standard reflections: 0

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.101
S = 1.05
2862 reflections
248 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4	0.88	2.00	2.661 (2)	131
C14—H14A⋯O4ⁱ	0.98	2.48	3.414 (2)	160
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809054889/cv2678sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809054889/cv2678Isup2.hkl

checkCIF report

Comment top

The present paper is a continuation of X-ray studies of a group of chromone derivatives (Małecka & Budzisz, 2006, Małecka, 2007). Due to their biological activity (Khan et al., 2009) and the presence of intramolecular N—H···O hydrogen bond which could be classified as resonanse assisted hydrogen bond (RAHB) (Gilli et al., 1994).

The more detailed insight into the molecular structure of the title compound shows that N—H···O hydrogen bond (Table 1) may be classified as resonance assisted hydrogen bond (RAHB). Such interactions RAHB have been investigated for homonuclear O—H···O interactions and for heteronuclear N—H···O RAHBs (Bertolasi et al., 1998).

Considering O4═C4—C3═C31—N1—H1 fragment it is not observed the equalization of C4—C3 and C3═C31 in comparison to previuos examined structures However, it was found the elongation and shortening of C4═O4 and C3—N1 bonds, respectively. The π- electron delocalization effect is not so evident as in earlier investigated structures. It is associated with lack of the planarity and non-aromatic character of main part of molecule.

The packing of the molecules in the crystal lattice is stabilized via C—H···O hydrogen bonds (Table 1). Atom C14 is involved in a weak C—H···O intermolecular interaction with atom O4 related by symmetry x, 1/2 - y, -1/2 + z what results in forming chains C(11) along c axis.

The six-memebered pyrone ring adopts HC conformation, what confirm the Cremer & Pople parameters Q_T= 0.396 (1) Å, ϕ₂= 62.3 (2)°, θ₂= 39.8 (3)°.

Bonds distances and angles are in a good agreement with expected values.

Related literature top

For the biological propertries of similar structures, see: Khan et al. (2009). For related structures, see: Gilli et al. (1994); Bertolasi et al. (1998); Małecka & Budzisz (2006); Małecka (2007).

Experimental top

4-Oxo-4H-1-benzopyran-3-carboxaldehyde (0.348 g, 0.002 mol) was dissolved in hot toluene (20 ml) together with a small amount of p-toluenesulphonic acid as a catalyst. Resulting solution was kept under reflux while the solution of 3,4,5-trimethoxyaniline (0.366 g, 0.002 mol) in toluene (20 ml) was slowly added. When the addition was finished, the solution was kept under reflux for following 3 h. Then it was left in room temperature for 24 h. Approximately half of the solvent was removed under reduced pressure and resulting solution was left in the refrigerator for 48 h. Obtained precipitate was filtered off, added to 30 ml of methanol and refluxed for 30 minutes. The hot solution was filtered off to remove insolubilities. Then it was left in room temperature for 2 h. Approximately half of the solvent was removed under reduced pressure. Next the solution was left in the refrigerator for 4 days. Resulting precipitate was filtered off, washed with small amount of methanol and diethyl ether and dried under reduced pressure.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

Fig. 1. Molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. The N1—H1···O4 hydrogen bond classified as resonance assisted hydrogen bond (RAHB) is shown as dashed line.

2-Methoxy-3-[(3,4,5-trimethoxyanilino)methylidene]-3,4-dihydro- 2H-1-benzopyran-4-one top

Crystal data top

C₂₀H₂₁NO₆	F(000) = 784
M_r = 371.38	D_x = 1.385 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 408.2 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54184 Å
a = 11.6145 (6) Å	Cell parameters from 4015 reflections
b = 20.8689 (9) Å	θ = 3.8–62.6°
c = 7.3728 (5) Å	µ = 0.86 mm⁻¹
β = 94.533 (5)°	T = 100 K
V = 1781.44 (17) Å³	Needle, light yellow
Z = 4	0.2 × 0.05 × 0.03 mm

Data collection top

Oxford Diffraction Gemini E Ultra diffractometer	2862 independent reflections
Radiation source: fine-focus sealed tube	2344 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω scans	θ_max = 62.7°, θ_min = 3.8°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −13→12
T_min = 0.844, T_max = 1.000	k = −23→24
7511 measured reflections	l = −8→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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0639P)² + 0.2369P] where P = (F_o² + 2F_c²)/3
2862 reflections	(Δ/σ)_max = 0.001
248 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₀H₂₁NO₆	V = 1781.44 (17) Å³
M_r = 371.38	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 11.6145 (6) Å	µ = 0.86 mm⁻¹
b = 20.8689 (9) Å	T = 100 K
c = 7.3728 (5) Å	0.2 × 0.05 × 0.03 mm
β = 94.533 (5)°

Data collection top

Oxford Diffraction Gemini E Ultra diffractometer	2862 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2344 reflections with I > 2σ(I)
T_min = 0.844, T_max = 1.000	R_int = 0.024
7511 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.05	Δρ_max = 0.38 e Å⁻³
2862 reflections	Δρ_min = −0.22 e Å⁻³
248 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
O1	1.23908 (9)	0.33541 (5)	0.31295 (15)	0.0255 (3)
O4	0.95775 (10)	0.38347 (5)	0.58323 (17)	0.0289 (3)
O2	1.09596 (10)	0.35060 (5)	0.07967 (15)	0.0260 (3)
O5	0.47817 (9)	0.21086 (5)	0.59973 (16)	0.0249 (3)
O6	0.53215 (9)	0.08807 (5)	0.56606 (15)	0.0238 (3)
O7	0.74024 (10)	0.05173 (5)	0.46838 (16)	0.0244 (3)
C2	1.12917 (14)	0.31326 (8)	0.2334 (2)	0.0235 (4)
H2	1.1368	0.2676	0.1952	0.028*
C3	1.03717 (14)	0.31789 (7)	0.3633 (2)	0.0210 (3)
C4	1.03657 (14)	0.37260 (8)	0.4811 (2)	0.0222 (4)
C5	1.14364 (15)	0.47322 (8)	0.5741 (2)	0.0275 (4)
H5	1.0785	0.4873	0.6335	0.033*
C6	1.24169 (16)	0.51097 (8)	0.5790 (2)	0.0310 (4)
H6	1.2445	0.5507	0.6421	0.037*
C7	1.33615 (15)	0.49006 (8)	0.4906 (2)	0.0316 (4)
H7	1.4031	0.5163	0.4924	0.038*
C8	1.33492 (15)	0.43197 (8)	0.3999 (2)	0.0285 (4)
H8	1.4003	0.4181	0.3407	0.034*
C9	1.13951 (14)	0.41457 (8)	0.4826 (2)	0.0226 (4)
C10	1.23612 (14)	0.39430 (8)	0.3972 (2)	0.0239 (4)
C31	0.95368 (14)	0.27129 (7)	0.3632 (2)	0.0205 (3)
H31	0.9631	0.2339	0.2922	0.025*
N1	0.86037 (11)	0.27528 (6)	0.45664 (18)	0.0204 (3)
H1	0.8488	0.3121	0.5103	0.025*
C33	0.77785 (14)	0.22652 (7)	0.4788 (2)	0.0189 (3)
C34	0.66962 (14)	0.24532 (7)	0.5266 (2)	0.0201 (3)
H34	0.6521	0.2894	0.5404	0.024*
C35	0.58738 (13)	0.19877 (7)	0.5540 (2)	0.0197 (3)
C36	0.61350 (14)	0.13378 (7)	0.5328 (2)	0.0209 (3)
C37	0.72250 (14)	0.11622 (7)	0.4839 (2)	0.0202 (3)
C38	0.80637 (14)	0.16237 (7)	0.4574 (2)	0.0198 (3)
H38	0.8810	0.1503	0.4257	0.024*
C12	0.44405 (15)	0.27643 (8)	0.6067 (2)	0.0270 (4)
H12A	0.4956	0.2992	0.6964	0.041*
H12B	0.3645	0.2791	0.6417	0.041*
H12C	0.4486	0.2960	0.4867	0.041*
C13	0.46540 (14)	0.06810 (8)	0.4033 (2)	0.0268 (4)
H13A	0.4261	0.1053	0.3458	0.040*
H13B	0.4079	0.0364	0.4343	0.040*
H13C	0.5167	0.0490	0.3188	0.040*
C14	0.85363 (14)	0.03145 (8)	0.4304 (2)	0.0270 (4)
H14A	0.8719	0.0485	0.3122	0.040*
H14B	0.8565	−0.0155	0.4275	0.040*
H14C	0.9101	0.0474	0.5255	0.040*
C11	1.18116 (17)	0.35023 (9)	−0.0509 (2)	0.0344 (4)
H11A	1.2485	0.3752	−0.0039	0.052*
H11B	1.1484	0.3693	−0.1651	0.052*
H11C	1.2047	0.3060	−0.0731	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0172 (6)	0.0308 (6)	0.0284 (6)	−0.0008 (5)	0.0019 (5)	−0.0014 (5)
O4	0.0269 (7)	0.0251 (6)	0.0361 (7)	−0.0055 (5)	0.0123 (6)	−0.0058 (5)
O2	0.0259 (6)	0.0284 (6)	0.0240 (6)	−0.0016 (5)	0.0044 (5)	0.0024 (5)
O5	0.0189 (6)	0.0225 (6)	0.0343 (7)	0.0013 (4)	0.0078 (5)	−0.0024 (5)
O6	0.0221 (6)	0.0213 (6)	0.0285 (6)	−0.0054 (4)	0.0056 (5)	0.0009 (5)
O7	0.0229 (6)	0.0163 (5)	0.0349 (7)	0.0006 (4)	0.0080 (5)	0.0002 (5)
C2	0.0197 (8)	0.0256 (8)	0.0253 (9)	−0.0017 (6)	0.0021 (7)	0.0022 (7)
C3	0.0188 (8)	0.0237 (8)	0.0204 (8)	−0.0001 (6)	0.0013 (6)	0.0012 (6)
C4	0.0198 (8)	0.0234 (8)	0.0234 (8)	−0.0014 (6)	0.0028 (7)	0.0037 (7)
C5	0.0277 (10)	0.0290 (9)	0.0260 (9)	−0.0047 (7)	0.0037 (7)	0.0025 (7)
C6	0.0344 (10)	0.0290 (9)	0.0288 (9)	−0.0099 (7)	−0.0031 (8)	0.0020 (7)
C7	0.0222 (9)	0.0375 (10)	0.0343 (10)	−0.0095 (7)	−0.0037 (8)	0.0096 (8)
C8	0.0179 (9)	0.0379 (10)	0.0294 (9)	−0.0026 (7)	0.0003 (7)	0.0062 (8)
C9	0.0214 (9)	0.0266 (8)	0.0196 (8)	−0.0038 (6)	0.0003 (6)	0.0032 (6)
C10	0.0215 (9)	0.0286 (8)	0.0210 (8)	−0.0010 (7)	−0.0016 (7)	0.0059 (7)
C31	0.0209 (8)	0.0227 (8)	0.0178 (7)	−0.0009 (6)	0.0004 (6)	0.0004 (6)
N1	0.0188 (7)	0.0194 (6)	0.0233 (7)	−0.0031 (5)	0.0023 (6)	−0.0007 (5)
C33	0.0189 (8)	0.0215 (8)	0.0162 (7)	−0.0031 (6)	0.0001 (6)	0.0009 (6)
C34	0.0212 (9)	0.0187 (7)	0.0204 (8)	−0.0008 (6)	0.0009 (6)	−0.0008 (6)
C35	0.0174 (8)	0.0228 (8)	0.0189 (8)	0.0012 (6)	0.0024 (6)	−0.0007 (6)
C36	0.0199 (8)	0.0218 (8)	0.0209 (8)	−0.0033 (6)	0.0025 (6)	0.0014 (6)
C37	0.0223 (8)	0.0186 (7)	0.0198 (8)	0.0005 (6)	0.0025 (6)	−0.0001 (6)
C38	0.0172 (8)	0.0223 (8)	0.0201 (8)	0.0004 (6)	0.0033 (6)	0.0008 (6)
C12	0.0229 (9)	0.0250 (8)	0.0333 (9)	0.0057 (7)	0.0036 (7)	−0.0035 (7)
C13	0.0213 (9)	0.0224 (8)	0.0365 (10)	−0.0035 (6)	0.0009 (7)	0.0008 (7)
C14	0.0238 (9)	0.0216 (8)	0.0364 (10)	0.0042 (6)	0.0085 (8)	0.0000 (7)
C11	0.0363 (11)	0.0399 (10)	0.0284 (9)	−0.0068 (8)	0.0118 (8)	−0.0006 (8)

Geometric parameters (Å, º) top

O1—C10	1.379 (2)	C9—C10	1.395 (2)
O1—C2	1.438 (2)	C31—N1	1.332 (2)
O4—C4	1.251 (2)	C31—H31	0.9500
O2—C2	1.4042 (19)	N1—C33	1.416 (2)
O2—C11	1.434 (2)	N1—H1	0.8800
O5—C35	1.3614 (19)	C33—C34	1.389 (2)
O5—C12	1.4267 (19)	C33—C38	1.391 (2)
O6—C36	1.3781 (19)	C34—C35	1.388 (2)
O6—C13	1.438 (2)	C34—H34	0.9500
O7—C37	1.3677 (18)	C35—C36	1.401 (2)
O7—C14	1.4318 (19)	C36—C37	1.393 (2)
C2—C3	1.493 (2)	C37—C38	1.394 (2)
C2—H2	1.0000	C38—H38	0.9500
C3—C31	1.373 (2)	C12—H12A	0.9800
C3—C4	1.435 (2)	C12—H12B	0.9800
C4—C9	1.481 (2)	C12—H12C	0.9800
C5—C6	1.383 (2)	C13—H13A	0.9800
C5—C9	1.397 (2)	C13—H13B	0.9800
C5—H5	0.9500	C13—H13C	0.9800
C6—C7	1.390 (3)	C14—H14A	0.9800
C6—H6	0.9500	C14—H14B	0.9800
C7—C8	1.384 (3)	C14—H14C	0.9800
C7—H7	0.9500	C11—H11A	0.9800
C8—C10	1.390 (2)	C11—H11B	0.9800
C8—H8	0.9500	C11—H11C	0.9800

C10—O1—C2	114.66 (12)	C34—C33—N1	117.44 (13)
C2—O2—C11	112.27 (13)	C38—C33—N1	120.61 (14)
C35—O5—C12	116.97 (12)	C35—C34—C33	119.10 (14)
C36—O6—C13	112.60 (12)	C35—C34—H34	120.4
C37—O7—C14	117.01 (12)	C33—C34—H34	120.4
O2—C2—O1	109.21 (12)	O5—C35—C34	124.86 (14)
O2—C2—C3	108.48 (13)	O5—C35—C36	114.91 (13)
O1—C2—C3	112.02 (13)	C34—C35—C36	120.23 (15)
O2—C2—H2	109.0	O6—C36—C37	120.92 (14)
O1—C2—H2	109.0	O6—C36—C35	119.52 (14)
C3—C2—H2	109.0	C37—C36—C35	119.53 (14)
C31—C3—C4	121.76 (15)	O7—C37—C36	115.26 (14)
C31—C3—C2	119.67 (14)	O7—C37—C38	123.80 (14)
C4—C3—C2	118.53 (14)	C36—C37—C38	120.93 (14)
O4—C4—C3	123.18 (14)	C33—C38—C37	118.27 (15)
O4—C4—C9	121.12 (15)	C33—C38—H38	120.9
C3—C4—C9	115.62 (14)	C37—C38—H38	120.9
C6—C5—C9	120.58 (17)	O5—C12—H12A	109.5
C6—C5—H5	119.7	O5—C12—H12B	109.5
C9—C5—H5	119.7	H12A—C12—H12B	109.5
C5—C6—C7	119.20 (17)	O5—C12—H12C	109.5
C5—C6—H6	120.4	H12A—C12—H12C	109.5
C7—C6—H6	120.4	H12B—C12—H12C	109.5
C8—C7—C6	121.54 (16)	O6—C13—H13A	109.5
C8—C7—H7	119.2	O6—C13—H13B	109.5
C6—C7—H7	119.2	H13A—C13—H13B	109.5
C7—C8—C10	118.64 (16)	O6—C13—H13C	109.5
C7—C8—H8	120.7	H13A—C13—H13C	109.5
C10—C8—H8	120.7	H13B—C13—H13C	109.5
C10—C9—C5	119.05 (15)	O7—C14—H14A	109.5
C10—C9—C4	119.66 (15)	O7—C14—H14B	109.5
C5—C9—C4	121.24 (15)	H14A—C14—H14B	109.5
O1—C10—C8	117.42 (15)	O7—C14—H14C	109.5
O1—C10—C9	121.56 (14)	H14A—C14—H14C	109.5
C8—C10—C9	120.98 (16)	H14B—C14—H14C	109.5
N1—C31—C3	123.98 (15)	O2—C11—H11A	109.5
N1—C31—H31	118.0	O2—C11—H11B	109.5
C3—C31—H31	118.0	H11A—C11—H11B	109.5
C31—N1—C33	126.91 (13)	O2—C11—H11C	109.5
C31—N1—H1	116.5	H11A—C11—H11C	109.5
C33—N1—H1	116.5	H11B—C11—H11C	109.5
C34—C33—C38	121.93 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.88	2.00	2.661 (2)	131
C14—H14A···O4ⁱ	0.98	2.48	3.414 (2)	160

Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₁NO₆
M_r	371.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	11.6145 (6), 20.8689 (9), 7.3728 (5)
β (°)	94.533 (5)
V (Å³)	1781.44 (17)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.86
Crystal size (mm)	0.2 × 0.05 × 0.03

Data collection
Diffractometer	Oxford Diffraction Gemini E Ultra diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.844, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7511, 2862, 2344
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.576

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.101, 1.05
No. of reflections	2862
No. of parameters	248
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.22

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.88	2.00	2.661 (2)	131
C14—H14A···O4ⁱ	0.98	2.48	3.414 (2)	160

Symmetry code: (i) x, −y+1/2, z−1/2.

Acknowledgements

Financial support from the University of Łódź and the Medical University of Łódź (grant No. 505/710 to MM and No. 502–13-701 to MC) is gratefully acknowledged. The authors thank Dr Oliver Presly from Oxford Diffraction for collecting the data.

References

Bertolasi, V., Gilli, P., Ferretti, V. & Gilli, G. (1998). Acta Cryst. B54, 50–65. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Gilli, P., Bertolasi, V., Ferretti, V. & Gilli, G. (1994). J. Am. Chem. Soc. 116, 909–915. CrossRef CAS Web of Science Google Scholar
Khan, K. M., Ambreen, N., Hussain, S., Perveen, S. & Choudhary, M. I. (2009). Bioorg. Med. Chem. 17, 2983–2988. Web of Science CrossRef PubMed CAS Google Scholar
Małecka, M. (2007). J. Mol. Struct. 831, 135–143. Google Scholar
Małecka, M. & Budzisz, E. (2006). Acta Cryst. E62, o5058–o5060. Web of Science CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

2-Meth­­oxy-3-[(3,4,5-tri­meth­oxy­anilino)methyl­­idene]-3,4-di­hydro-2H-1-benzo­pyran-4-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-Methoxy-3-[(3,4,5-trimethoxyanilino)methylidene]-3,4-dihydro-2H-1-benzopyran-4-one