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The title compound, C16H10Cl2N2O3·C2H6O, was synthesized by the reaction of 4-hydroxy-6-methyl­pyran-2-one, 2,4-di­chloro­benz­aldehyde and malono­nitrile in the presence of triethyl­benzyl­ammonium chloride in an aqueous medium. X-ray analysis reveals that the pyran­one ring is almost planar, while the pyran ring adopts a flattened boat conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804025127/ob6419sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804025127/ob6419Isup2.hkl
Contains datablock I

CCDC reference: 255891

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.004 Å
  • H-atom completeness 69%
  • Disorder in solvent or counterion
  • R factor = 0.050
  • wR factor = 0.147
  • Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C CELLV02_ALERT_1_C The supplied cell volume s.u. differs from that calculated from the cell parameter s.u.'s by > 2 Calculated cell volume su = 20.49 Cell volume su given = 18.00 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 2 From the CIF: _chemical_formula_weight 395.23 TEST: Calculate formula weight from _atom_site_* atom mass num sum C 12.01 18.00 216.20 H 1.01 11.00 11.09 Cl 35.45 2.00 70.91 N 14.01 2.00 28.01 O 16.00 4.00 64.00 Calculated formula weight 390.20 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 ................ 395.23 PLAT044_ALERT_1_C Calculated and Reported Dx Differ .............. ? PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 25.00 Perc. PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 33 C1 -C2 -C9 -N2 162.00 13.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 34 C3 -C2 -C9 -N2 -16.00 13.00 1.555 1.555 1.555 1.555
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:C18 H16 Cl2 N2 O4 Atom count from the _atom_site data: C18 H11 Cl2 N2 O4 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 2 From the CIF: _chemical_formula_sum C18 H16 Cl2 N2 O4 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 36.00 36.00 0.00 H 32.00 22.00 10.00 Cl 4.00 4.00 0.00 N 4.00 4.00 0.00 O 8.00 8.00 0.00
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 9 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 3 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.

2-Amino-3-cyano-4-(2,4-dichlorophenyl)-8-methylpyrano[3,2-c]pyran-5(4H)-one ethanol solvate top
Crystal data top
C16H10Cl2N2O3·C2H6OZ = 2
Mr = 395.23F(000) = 408
Triclinic, P1Dx = 1.406 Mg m3
Hall symbol: -P 1Melting point = 503–504 K
a = 9.2879 (12) ÅMo Kα radiation, λ = 0.71070 Å
b = 10.4526 (12) ÅCell parameters from 3571 reflections
c = 11.0678 (10) Åθ = 3.0–25.3°
α = 63.905 (10)°µ = 0.37 mm1
β = 75.826 (14)°T = 193 K
γ = 80.288 (15)°Block, colorless
V = 933.29 (18) Å30.50 × 0.31 × 0.20 mm
Data collection top
Rigaku Mercury
diffractometer
3403 independent reflections
Radiation source: fine-focus sealed tube2985 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
Detector resolution: 7.31 pixels mm-1θmax = 25.4°, θmin = 3.3°
ω scansh = 1011
Absorption correction: multi-scan
(Jacobson, 1998)
k = 1212
Tmin = 0.835, Tmax = 0.929l = 1113
9269 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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0852P)2 + 0.4955P]
where P = (Fo2 + 2Fc2)/3
3403 reflections(Δ/σ)max = 0.001
258 parametersΔρmax = 0.65 e Å3
2 restraintsΔρmin = 0.43 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)
Cl10.13535 (7)0.13002 (7)0.90105 (6)0.0371 (2)
Cl20.42099 (14)0.35050 (10)0.88044 (11)0.0789 (4)
O10.01040 (18)0.44676 (18)0.69492 (18)0.0300 (4)
O20.0972 (2)0.0657 (2)0.6044 (2)0.0395 (5)
O30.27994 (19)0.1663 (2)0.71198 (19)0.0351 (4)
O40.0135 (3)0.2371 (2)0.3022 (2)0.0526 (6)
N10.1967 (3)0.5552 (2)0.6383 (3)0.0344 (5)
N20.4792 (2)0.3789 (3)0.4595 (3)0.0400 (6)
C10.1377 (3)0.4510 (3)0.6331 (2)0.0261 (5)
C20.2047 (3)0.3575 (3)0.5777 (2)0.0260 (5)
C30.1283 (3)0.2354 (2)0.5865 (2)0.0257 (5)
H30.13550.24670.49070.031*
C40.0338 (3)0.2500 (3)0.6468 (2)0.0261 (5)
C50.0928 (3)0.3496 (3)0.6958 (2)0.0262 (5)
C60.1320 (3)0.1556 (3)0.6500 (3)0.0298 (6)
C70.3347 (3)0.2676 (3)0.7613 (3)0.0327 (6)
C80.2458 (3)0.3597 (3)0.7544 (3)0.0308 (6)
H80.28440.43050.78800.037*
C90.3559 (3)0.3707 (3)0.5124 (3)0.0286 (5)
C100.2035 (2)0.0898 (3)0.6642 (3)0.0252 (5)
C110.2106 (3)0.0333 (3)0.8029 (3)0.0291 (5)
C120.2769 (3)0.1000 (3)0.8696 (3)0.0395 (6)
H120.27880.13650.96450.047*
C130.3407 (3)0.1795 (3)0.7954 (3)0.0446 (7)
C140.3400 (3)0.1281 (3)0.6580 (3)0.0413 (7)
H140.38610.18290.60780.050*
C150.2705 (3)0.0053 (3)0.5946 (3)0.0340 (6)
H150.26840.04070.49990.041*
C160.4959 (3)0.2581 (4)0.8216 (3)0.0445 (7)
H16A0.53220.33710.84880.067*
H16B0.51180.16700.90230.067*
H16C0.55020.26390.75370.067*
C170.0689 (7)0.2488 (5)0.1691 (4)0.0993 (18)
C18A0.2278 (16)0.2732 (18)0.1393 (17)0.130 (6)0.45
C18B0.1302 (18)0.3840 (11)0.0673 (9)0.133 (5)0.55
H1A0.137 (3)0.621 (3)0.657 (3)0.035 (8)*
H1B0.281 (4)0.567 (3)0.609 (3)0.039 (9)*
H40.010 (5)0.149 (5)0.363 (4)0.076 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0425 (4)0.0398 (4)0.0317 (4)0.0020 (3)0.0049 (3)0.0188 (3)
Cl20.1105 (9)0.0423 (5)0.0759 (7)0.0369 (5)0.0395 (6)0.0212 (5)
O10.0236 (9)0.0298 (9)0.0420 (10)0.0032 (7)0.0019 (7)0.0216 (8)
O20.0398 (11)0.0341 (10)0.0542 (12)0.0060 (8)0.0089 (9)0.0259 (10)
O30.0279 (9)0.0352 (10)0.0432 (11)0.0073 (7)0.0056 (8)0.0162 (9)
O40.0723 (16)0.0337 (12)0.0480 (13)0.0006 (11)0.0030 (11)0.0197 (11)
N10.0261 (12)0.0320 (12)0.0519 (15)0.0045 (10)0.0009 (10)0.0262 (11)
N20.0287 (13)0.0404 (13)0.0563 (15)0.0060 (10)0.0030 (11)0.0294 (12)
C10.0226 (12)0.0255 (12)0.0299 (12)0.0022 (9)0.0047 (9)0.0111 (10)
C20.0254 (12)0.0230 (12)0.0295 (12)0.0031 (9)0.0035 (9)0.0112 (10)
C30.0273 (12)0.0238 (12)0.0281 (12)0.0022 (9)0.0047 (9)0.0130 (10)
C40.0258 (12)0.0238 (12)0.0285 (12)0.0020 (9)0.0071 (9)0.0096 (10)
C50.0251 (12)0.0246 (12)0.0289 (12)0.0042 (9)0.0064 (9)0.0096 (10)
C60.0281 (13)0.0284 (13)0.0321 (13)0.0033 (10)0.0074 (10)0.0105 (11)
C70.0270 (13)0.0359 (14)0.0314 (13)0.0015 (10)0.0063 (10)0.0104 (11)
C80.0256 (12)0.0314 (13)0.0352 (14)0.0004 (10)0.0035 (10)0.0156 (11)
C90.0308 (14)0.0237 (12)0.0346 (13)0.0027 (10)0.0050 (11)0.0154 (11)
C100.0212 (11)0.0250 (12)0.0309 (12)0.0041 (9)0.0044 (9)0.0124 (10)
C110.0285 (13)0.0278 (13)0.0328 (13)0.0022 (10)0.0036 (10)0.0154 (11)
C120.0446 (16)0.0345 (15)0.0375 (15)0.0020 (12)0.0138 (12)0.0121 (12)
C130.0483 (17)0.0298 (15)0.0534 (18)0.0108 (12)0.0192 (14)0.0152 (13)
C140.0431 (16)0.0330 (15)0.0535 (18)0.0061 (12)0.0105 (13)0.0257 (14)
C150.0360 (14)0.0321 (14)0.0380 (14)0.0004 (11)0.0070 (11)0.0190 (12)
C160.0274 (14)0.0550 (19)0.0495 (17)0.0074 (13)0.0029 (12)0.0210 (15)
C170.162 (5)0.075 (3)0.049 (2)0.015 (3)0.009 (3)0.027 (2)
C18A0.143 (12)0.121 (12)0.129 (12)0.070 (10)0.061 (10)0.079 (11)
C18B0.236 (15)0.082 (7)0.046 (5)0.026 (8)0.035 (7)0.021 (5)
Geometric parameters (Å, º) top
Cl1—C111.745 (2)C4—C61.437 (3)
Cl2—C131.746 (3)C5—C81.417 (3)
O1—C51.366 (3)C7—C81.337 (4)
O1—C11.377 (3)C7—C161.483 (4)
O2—C61.215 (3)C8—H80.9500
O3—C71.367 (3)C10—C151.392 (4)
O3—C61.387 (3)C10—C111.397 (4)
O4—C171.393 (5)C11—C121.376 (4)
O4—H40.87 (5)C12—C131.383 (4)
N1—C11.327 (3)C12—H120.9500
N1—H1A0.87 (3)C13—C141.374 (4)
N1—H1B0.78 (3)C14—C151.382 (4)
N2—C91.150 (3)C14—H140.9500
C1—C21.361 (3)C15—H150.9500
C2—C91.412 (3)C16—H16A0.9800
C2—C31.518 (3)C16—H16B0.9800
C3—C41.502 (3)C16—H16C0.9800
C3—C101.526 (3)C17—C18B1.466 (10)
C3—H31.0000C17—C18A1.473 (14)
C4—C51.356 (3)
C5—O1—C1118.89 (18)C7—C8—H8120.7
C7—O3—C6122.3 (2)C5—C8—H8120.7
C17—O4—H4113 (3)N2—C9—C2178.7 (3)
C1—N1—H1A119 (2)C15—C10—C11116.4 (2)
C1—N1—H1B120 (2)C15—C10—C3119.1 (2)
H1A—N1—H1B120 (3)C11—C10—C3124.4 (2)
N1—C1—C2128.6 (2)C12—C11—C10122.5 (2)
N1—C1—O1109.9 (2)C12—C11—Cl1116.4 (2)
C2—C1—O1121.6 (2)C10—C11—Cl1121.16 (19)
C1—C2—C9118.5 (2)C11—C12—C13118.5 (3)
C1—C2—C3123.9 (2)C11—C12—H12120.8
C9—C2—C3117.5 (2)C13—C12—H12120.8
C4—C3—C2108.54 (19)C14—C13—C12121.6 (3)
C4—C3—C10113.02 (19)C14—C13—Cl2119.7 (2)
C2—C3—C10112.40 (19)C12—C13—Cl2118.7 (2)
C4—C3—H3107.5C13—C14—C15118.4 (3)
C2—C3—H3107.5C13—C14—H14120.8
C10—C3—H3107.5C15—C14—H14120.8
C5—C4—C6118.3 (2)C14—C15—C10122.6 (3)
C5—C4—C3123.4 (2)C14—C15—H15118.7
C6—C4—C3118.4 (2)C10—C15—H15118.7
C4—C5—O1123.2 (2)C7—C16—H16A109.5
C4—C5—C8122.3 (2)C7—C16—H16B109.5
O1—C5—C8114.5 (2)H16A—C16—H16B109.5
O2—C6—O3116.6 (2)C7—C16—H16C109.5
O2—C6—C4125.9 (2)H16A—C16—H16C109.5
O3—C6—C4117.4 (2)H16B—C16—H16C109.5
C8—C7—O3120.9 (2)O4—C17—C18B117.3 (5)
C8—C7—C16126.9 (3)O4—C17—C18A106.2 (7)
O3—C7—C16112.2 (2)C18B—C17—C18A57.3 (9)
C7—C8—C5118.6 (2)
C5—O1—C1—N1177.7 (2)C6—O3—C7—C81.5 (4)
C5—O1—C1—C22.5 (3)C6—O3—C7—C16179.5 (2)
N1—C1—C2—C92.0 (4)O3—C7—C8—C50.6 (4)
O1—C1—C2—C9178.2 (2)C16—C7—C8—C5178.3 (3)
N1—C1—C2—C3175.6 (2)C4—C5—C8—C70.0 (4)
O1—C1—C2—C34.2 (4)O1—C5—C8—C7179.1 (2)
C1—C2—C3—C47.9 (3)C1—C2—C9—N2162 (13)
C9—C2—C3—C4174.6 (2)C3—C2—C9—N216 (13)
C1—C2—C3—C10117.9 (3)C4—C3—C10—C15121.3 (2)
C9—C2—C3—C1059.7 (3)C2—C3—C10—C15115.4 (2)
C2—C3—C4—C55.8 (3)C4—C3—C10—C1158.8 (3)
C10—C3—C4—C5119.6 (3)C2—C3—C10—C1164.5 (3)
C2—C3—C4—C6172.8 (2)C15—C10—C11—C121.4 (4)
C10—C3—C4—C661.8 (3)C3—C10—C11—C12178.6 (2)
C6—C4—C5—O1178.5 (2)C15—C10—C11—Cl1178.30 (18)
C3—C4—C5—O10.1 (4)C3—C10—C11—Cl11.6 (3)
C6—C4—C5—C82.5 (4)C10—C11—C12—C131.0 (4)
C3—C4—C5—C8178.9 (2)Cl1—C11—C12—C13178.7 (2)
C1—O1—C5—C44.6 (3)C11—C12—C13—C140.4 (5)
C1—O1—C5—C8176.3 (2)C11—C12—C13—Cl2178.4 (2)
C7—O3—C6—O2176.8 (2)C12—C13—C14—C151.4 (5)
C7—O3—C6—C43.9 (3)Cl2—C13—C14—C15177.5 (2)
C5—C4—C6—O2176.5 (2)C13—C14—C15—C100.9 (4)
C3—C4—C6—O22.2 (4)C11—C10—C15—C140.4 (4)
C5—C4—C6—O34.3 (3)C3—C10—C15—C14179.6 (2)
C3—C4—C6—O3177.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14···N2i0.952.523.439 (4)164
O4—H4···O20.87 (5)2.42 (4)3.020 (3)127 (3)
O4—H4···O2ii0.87 (5)2.15 (5)2.894 (3)143 (4)
N1—H1B···N2iii0.78 (3)2.26 (3)3.026 (3)172 (3)
N1—H1A···O4iv0.87 (3)1.99 (3)2.856 (3)175 (3)
Symmetry codes: (i) x+1, y, z+1; (ii) x, y, z+1; (iii) x+1, y+1, z+1; (iv) x, y+1, z+1.
 

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