2-Meth-oxy-3-[(3,4,5-trimethoxy-anilino)methyl-idene]-3,4-dihydro-2H-1-benzopyran-4-one.

The title mol-ecule, C(20)H(21)NO(6), adopts a keto-amine tautomeric form. An intra-molecular N-H⋯O hydrogen bond, classified as a resonanse-assisted hydrogen bond, influences the mol-ecular conformation; the two benzene rings form a dihedral angle of 24.6 (1)°. In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds link mol-ecules 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 = 371.38

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.101

S = 1.05

2862 reflections

248 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); 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.

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

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

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

C20H21NO6	F(000) = 784
Mr = 371.38	Dx = 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

Oxford Diffraction Gemini E Ultra diffractometer	2862 independent reflections
Radiation source: fine-focus sealed tube	2344 reflections with I > 2σ(I)
graphite	Rint = 0.024
ω scans	θmax = 62.7°, θmin = 3.8°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −13→12
Tmin = 0.844, Tmax = 1.000	k = −23→24
7511 measured reflections	l = −8→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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0639P)2 + 0.2369P] where P = (Fo2 + 2Fc2)/3
2862 reflections	(Δ/σ)max = 0.001
248 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.22 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
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*

	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)

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)

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

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) .