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The title compound, C19H19NO6, was synthesized by the reaction of 4-hydroxy-6-methyl­pyran-2-one and ethyl 4′-methoxy-2-cyano­cinnamate in the presence of triethyl­benzyl­ammonium chloride in an aqueous medium. The pyran­one ring is almost planar, while the fused pyran ring adopts a flattened boat conformation. The amino group is involved in both intra- and intermolecular N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804029332/ob6422sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804029332/ob6422Isup2.hkl
Contains datablock I

CCDC reference: 259592

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.003 Å
  • H-atom completeness 74%
  • R factor = 0.059
  • wR factor = 0.163
  • Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT432_ALERT_2_A Short Inter X...Y Contact C11B .. C11B .. 2.30 Ang.
Alert level C CHEMW03_ALERT_2_C The ratio of given/expected molecular weight as calculated from the _atom_site* data lies outside the range 0.99 <> 1.01 From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_weight 357.35 TEST: Calculate formula weight from _atom_site_* atom mass num sum C 12.01 19.00 228.21 H 1.01 14.00 14.11 N 14.01 1.00 14.01 O 16.00 6.00 95.99 Calculated formula weight 352.32 DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.692 Test value = 0.600 DIFMX02_ALERT_1_C The minimum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT043_ALERT_1_C Check Reported Molecular Weight ................ 357.35 PLAT044_ALERT_1_C Calculated and Reported Dx Differ .............. ? PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.75 mm PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.39 PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.69 e/A   3 PLAT301_ALERT_3_C Main Residue Disorder ......................... 4.00 Perc.
Alert level G FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C19 H19 N1 O6 Atom count from the _atom_site data: C19 H14 N1 O6 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional? From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_sum C19 H19 N O6 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 76.00 76.00 0.00 H 76.00 56.00 20.00 N 4.00 4.00 0.00 O 24.00 24.00 0.00
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2003); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Ethyl 2-amino-4-(4-methoxyphenyl)-7-methyl-5-oxopyrano[3,2-c]pyran-3-carboxylate top
Crystal data top
C19H19NO6F(000) = 752
Mr = 357.35Dx = 1.369 Mg m3
Monoclinic, P21/cMelting point = 445–447 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71070 Å
a = 10.720 (4) ÅCell parameters from 7929 reflections
b = 8.934 (3) Åθ = 3.1–27.5°
c = 18.167 (6) ŵ = 0.10 mm1
β = 94.636 (7)°T = 193 K
V = 1734.2 (10) Å3Block, colorless
Z = 40.75 × 0.65 × 0.45 mm
Data collection top
Rigaku Mercury
diffractometer
3947 independent reflections
Radiation source: fine-focus sealed tube3575 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
Detector resolution: 7.31 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = 1313
Absorption correction: multi-scan
(Jacobson, 1998)
k = 1011
Tmin = 0.914, Tmax = 0.955l = 2323
18580 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0836P)2 + 0.9423P]
where P = (Fo2 + 2Fc2)/3
3947 reflections(Δ/σ)max < 0.001
255 parametersΔρmax = 0.69 e Å3
2 restraintsΔρmin = 0.29 e Å3
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
xyzUiso*/UeqOcc. (<1)
O11.05143 (13)0.37011 (14)0.17071 (8)0.0316 (3)
O21.02879 (14)0.89867 (15)0.14269 (9)0.0384 (4)
O31.16290 (12)0.79486 (14)0.22669 (8)0.0310 (3)
O40.79150 (16)0.27396 (18)0.00755 (9)0.0469 (4)
O50.76468 (14)0.52090 (18)0.02776 (8)0.0413 (4)
O60.45344 (14)0.85568 (19)0.17062 (9)0.0431 (4)
N10.9670 (2)0.19416 (19)0.09623 (12)0.0398 (4)
C10.96960 (18)0.3413 (2)0.11009 (11)0.0289 (4)
C20.90380 (17)0.4511 (2)0.07134 (10)0.0279 (4)
C30.91786 (16)0.61697 (19)0.09104 (10)0.0250 (4)
H30.94300.67130.04640.030*
C41.02227 (16)0.63387 (19)0.15156 (10)0.0247 (4)
C51.07889 (17)0.51683 (19)0.18778 (10)0.0266 (4)
C61.06648 (17)0.7822 (2)0.17081 (11)0.0281 (4)
C71.21540 (18)0.6730 (2)0.26323 (10)0.0298 (4)
C81.17603 (18)0.5343 (2)0.24587 (11)0.0303 (4)
H81.21160.44980.27140.036*
C90.81762 (18)0.4041 (2)0.01014 (11)0.0333 (4)
C100.6638 (2)0.4798 (4)0.08306 (14)0.0574 (7)
C11A0.6161 (4)0.6173 (4)0.1181 (2)0.0566 (10)0.72
C11B0.5482 (8)0.5342 (13)0.0517 (6)0.059 (3)0.28
C120.79546 (17)0.6860 (2)0.11309 (10)0.0252 (4)
C130.73489 (18)0.7965 (2)0.07003 (10)0.0301 (4)
H130.77280.83320.02810.036*
C140.61962 (18)0.8553 (2)0.08662 (10)0.0317 (4)
H140.57900.92940.05580.038*
C150.56546 (18)0.8044 (2)0.14825 (11)0.0302 (4)
C160.62577 (18)0.6950 (2)0.19298 (11)0.0322 (4)
H160.58870.66020.23560.039*
C170.73989 (18)0.6369 (2)0.17534 (10)0.0286 (4)
H170.78040.56270.20620.034*
C180.38029 (19)0.9528 (3)0.12169 (14)0.0422 (5)
H18A0.42721.04510.11440.063*
H18B0.30180.97720.14310.063*
H18C0.36180.90270.07410.063*
C191.3171 (2)0.7173 (2)0.31962 (12)0.0380 (5)
H19A1.35660.62740.34180.057*
H19B1.28190.77730.35810.057*
H19C1.37980.77640.29610.057*
H1A0.914 (3)0.169 (3)0.0590 (16)0.049 (7)*
H1B1.010 (3)0.132 (3)0.1260 (16)0.055 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0386 (7)0.0186 (6)0.0363 (7)0.0021 (5)0.0045 (6)0.0018 (5)
O20.0410 (8)0.0195 (6)0.0530 (9)0.0043 (6)0.0061 (7)0.0038 (6)
O30.0290 (7)0.0231 (6)0.0398 (8)0.0017 (5)0.0039 (6)0.0012 (5)
O40.0494 (9)0.0363 (8)0.0532 (10)0.0015 (7)0.0067 (7)0.0157 (7)
O50.0396 (8)0.0424 (9)0.0393 (8)0.0126 (7)0.0130 (6)0.0113 (7)
O60.0315 (8)0.0492 (9)0.0494 (9)0.0122 (7)0.0089 (6)0.0016 (7)
N10.0494 (11)0.0188 (8)0.0497 (11)0.0026 (7)0.0057 (9)0.0027 (7)
C10.0308 (9)0.0226 (9)0.0334 (9)0.0001 (7)0.0029 (7)0.0020 (7)
C20.0293 (9)0.0229 (8)0.0314 (9)0.0026 (7)0.0010 (7)0.0036 (7)
C30.0270 (9)0.0206 (8)0.0272 (8)0.0037 (7)0.0009 (7)0.0007 (7)
C40.0258 (8)0.0197 (8)0.0286 (9)0.0027 (6)0.0016 (7)0.0004 (7)
C50.0297 (9)0.0193 (8)0.0307 (9)0.0008 (7)0.0026 (7)0.0013 (7)
C60.0269 (9)0.0227 (9)0.0343 (10)0.0035 (7)0.0007 (7)0.0003 (7)
C70.0291 (9)0.0294 (9)0.0308 (9)0.0042 (7)0.0010 (7)0.0011 (7)
C80.0332 (9)0.0255 (9)0.0315 (9)0.0048 (7)0.0010 (7)0.0041 (7)
C90.0312 (10)0.0326 (10)0.0360 (10)0.0055 (8)0.0011 (8)0.0080 (8)
C100.0393 (12)0.082 (2)0.0471 (13)0.0092 (13)0.0191 (10)0.0154 (13)
C11A0.062 (2)0.0421 (18)0.060 (2)0.0145 (16)0.0279 (18)0.0011 (16)
C11B0.034 (4)0.078 (7)0.064 (6)0.002 (4)0.002 (4)0.023 (5)
C120.0269 (8)0.0203 (8)0.0278 (9)0.0012 (7)0.0013 (7)0.0026 (7)
C130.0341 (10)0.0279 (9)0.0283 (9)0.0058 (7)0.0024 (7)0.0031 (7)
C140.0328 (10)0.0292 (9)0.0323 (9)0.0090 (8)0.0022 (7)0.0018 (8)
C150.0262 (9)0.0285 (9)0.0357 (10)0.0024 (7)0.0008 (7)0.0062 (8)
C160.0334 (10)0.0309 (10)0.0325 (10)0.0004 (8)0.0040 (8)0.0009 (8)
C170.0330 (9)0.0218 (8)0.0304 (9)0.0017 (7)0.0009 (7)0.0024 (7)
C180.0280 (10)0.0362 (11)0.0619 (14)0.0068 (8)0.0000 (9)0.0036 (10)
C190.0332 (10)0.0376 (11)0.0416 (11)0.0005 (8)0.0063 (8)0.0015 (9)
Geometric parameters (Å, º) top
O1—C51.373 (2)C7—C81.339 (3)
O1—C11.376 (2)C7—C191.488 (3)
O2—C61.214 (2)C8—H80.9500
O3—C71.372 (2)C10—C11A1.457 (4)
O3—C61.394 (2)C10—C11B1.487 (9)
O4—C91.232 (3)C12—C131.388 (3)
O5—C91.350 (3)C12—C171.391 (3)
O5—C101.462 (3)C13—C141.398 (3)
O6—C151.377 (2)C13—H130.9500
O6—C181.430 (3)C14—C151.379 (3)
N1—C11.339 (2)C14—H140.9500
N1—H1A0.88 (3)C15—C161.396 (3)
N1—H1B0.88 (3)C16—C171.390 (3)
C1—C21.369 (3)C16—H160.9500
C2—C91.449 (3)C17—H170.9500
C2—C31.529 (2)C18—H18A0.9800
C3—C41.512 (2)C18—H18B0.9800
C3—C121.532 (2)C18—H18C0.9800
C3—H31.0000C19—H19A0.9800
C4—C51.353 (2)C19—H19B0.9800
C4—C61.441 (2)C19—H19C0.9800
C5—C81.430 (3)
C5—O1—C1118.05 (14)O4—C9—C2126.21 (19)
C7—O3—C6122.63 (15)O5—C9—C2112.52 (17)
C9—O5—C10114.43 (19)C11A—C10—O5107.6 (3)
C15—O6—C18117.77 (17)C11A—C10—C11B67.6 (5)
C1—N1—H1A113.4 (19)O5—C10—C11B104.4 (4)
C1—N1—H1B120.2 (19)C13—C12—C17118.11 (17)
H1A—N1—H1B126 (3)C13—C12—C3120.71 (16)
N1—C1—C2127.21 (19)C17—C12—C3121.15 (16)
N1—C1—O1109.66 (17)C12—C13—C14121.81 (18)
C2—C1—O1123.13 (16)C12—C13—H13119.1
C1—C2—C9117.19 (17)C14—C13—H13119.1
C1—C2—C3122.47 (17)C15—C14—C13119.26 (17)
C9—C2—C3120.34 (16)C15—C14—H14120.4
C4—C3—C2108.68 (14)C13—C14—H14120.4
C4—C3—C12111.66 (14)O6—C15—C14124.35 (18)
C2—C3—C12112.41 (15)O6—C15—C16115.79 (18)
C4—C3—H3108.0C14—C15—C16119.85 (17)
C2—C3—H3108.0C17—C16—C15120.14 (18)
C12—C3—H3108.0C17—C16—H16119.9
C5—C4—C6117.84 (16)C15—C16—H16119.9
C5—C4—C3123.59 (16)C16—C17—C12120.81 (17)
C6—C4—C3118.56 (15)C16—C17—H17119.6
C4—C5—O1123.25 (17)C12—C17—H17119.6
C4—C5—C8123.09 (17)O6—C18—H18A109.5
O1—C5—C8113.62 (15)O6—C18—H18B109.5
O2—C6—O3116.05 (16)H18A—C18—H18B109.5
O2—C6—C4126.47 (17)O6—C18—H18C109.5
O3—C6—C4117.48 (15)H18A—C18—H18C109.5
C8—C7—O3120.76 (17)H18B—C18—H18C109.5
C8—C7—C19127.43 (18)C7—C19—H19A109.5
O3—C7—C19111.80 (17)C7—C19—H19B109.5
C7—C8—C5118.14 (17)H19A—C19—H19B109.5
C7—C8—H8120.9C7—C19—H19C109.5
C5—C8—H8120.9H19A—C19—H19C109.5
O4—C9—O5121.27 (19)H19B—C19—H19C109.5
C5—O1—C1—N1171.80 (17)O3—C7—C8—C50.7 (3)
C5—O1—C1—C27.7 (3)C19—C7—C8—C5177.95 (18)
N1—C1—C2—C92.7 (3)C4—C5—C8—C72.4 (3)
O1—C1—C2—C9177.93 (17)O1—C5—C8—C7175.62 (17)
N1—C1—C2—C3177.92 (19)C10—O5—C9—O48.1 (3)
O1—C1—C2—C31.5 (3)C10—O5—C9—C2171.49 (17)
C1—C2—C3—C46.1 (2)C1—C2—C9—O45.1 (3)
C9—C2—C3—C4174.46 (16)C3—C2—C9—O4174.31 (19)
C1—C2—C3—C12117.98 (19)C1—C2—C9—O5175.30 (17)
C9—C2—C3—C1261.4 (2)C3—C2—C9—O55.3 (3)
C2—C3—C4—C58.5 (2)C9—O5—C10—C11A179.4 (2)
C12—C3—C4—C5116.05 (19)C9—O5—C10—C11B108.8 (5)
C2—C3—C4—C6169.94 (15)C4—C3—C12—C13123.04 (18)
C12—C3—C4—C665.5 (2)C2—C3—C12—C13114.52 (19)
C6—C4—C5—O1175.11 (17)C4—C3—C12—C1759.0 (2)
C3—C4—C5—O13.3 (3)C2—C3—C12—C1763.5 (2)
C6—C4—C5—C82.7 (3)C17—C12—C13—C141.7 (3)
C3—C4—C5—C8178.82 (17)C3—C12—C13—C14176.32 (17)
C1—O1—C5—C45.3 (3)C12—C13—C14—C151.3 (3)
C1—O1—C5—C8172.70 (15)C18—O6—C15—C148.9 (3)
C7—O3—C6—O2179.64 (17)C18—O6—C15—C16171.93 (18)
C7—O3—C6—C40.2 (3)C13—C14—C15—O6178.94 (18)
C5—C4—C6—O2177.95 (19)C13—C14—C15—C160.2 (3)
C3—C4—C6—O20.6 (3)O6—C15—C16—C17179.54 (17)
C5—C4—C6—O31.4 (3)C14—C15—C16—C170.3 (3)
C3—C4—C6—O3179.92 (15)C15—C16—C17—C120.2 (3)
C6—O3—C7—C80.6 (3)C13—C12—C17—C161.2 (3)
C6—O3—C7—C19179.39 (16)C3—C12—C17—C16176.86 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C18—H18C···O4i0.982.523.344 (3)142
C19—H19C···O6ii0.982.573.410 (3)144
N1—H1A···O40.88 (3)1.95 (3)2.651 (3)136 (3)
N1—H1B···O2iii0.88 (3)2.11 (3)2.834 (2)139 (2)
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z; (iii) x, y1, z.
 

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