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The title compound [systematic name: 2-amino-4-(3,4-di­chloro­phenyl)-5-oxo-4H,5H-pyrano­[3,2-c]­chromene-3-carbo­nitrile N,N-di­methyl­form­amide solvate], C19H10Cl2N2O3·C3H7NO, was synthesized by the reaction of 4-hydroxy­coumarin and 3′,4′-di­chloro­benzyl­idene­malono­nitrile, catal­ysed by KF-montmorillonite. In the crystal structure, the amino group is involved in intermolecular N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804028995/ob6427sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804028995/ob6427Isup2.hkl
Contains datablock I

CCDC reference: 259584

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.039
  • wR factor = 0.094
  • Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.65 mm PLAT230_ALERT_2_C Hirshfeld Test Diff for C2 - C13 .. 6.04 su PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C13 ... 1.42 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact N2 .. C20 .. 2.99 Ang. PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 44 C1 -C2 -C13 -N2 180.00100.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 45 C3 -C2 -C13 -N2 1.00 3.00 1.555 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 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.

2-amino-4-(3,4-dichlorophenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile N,N-dimethylformamide solvate top
Crystal data top
C19H10Cl2N2O3·C3H7NOF(000) = 1888
Mr = 458.29Dx = 1.473 Mg m3
Monoclinic, C2/cMelting point = 520–521 K
Hall symbol: -c 2ycMo Kα radiation, λ = 0.71070 Å
a = 28.126 (6) ÅCell parameters from 8932 reflections
b = 7.8824 (13) Åθ = 3.1–27.5°
c = 22.096 (5) ŵ = 0.35 mm1
β = 122.493 (3)°T = 193 K
V = 4131.8 (14) Å3Block, colorless
Z = 80.65 × 0.55 × 0.24 mm
Data collection top
Rigaku Mercury
diffractometer
4722 independent reflections
Radiation source: fine-focus sealed tube4404 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
Detector resolution: 7.31 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = 3636
Absorption correction: multi-scan
(Jacobson, 1998)
k = 1010
Tmin = 0.804, Tmax = 0.921l = 2828
22202 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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.0398P)2 + 3.5942P]
where P = (Fo2 + 2Fc2)/3
4722 reflections(Δ/σ)max < 0.001
291 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.23 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*/Ueq
Cl10.201189 (16)0.09716 (6)0.201572 (19)0.03568 (11)
Cl20.144301 (15)0.32666 (6)0.26267 (2)0.03675 (12)
O10.42061 (4)0.25673 (12)0.43864 (6)0.0251 (2)
O20.42875 (5)0.34191 (14)0.42423 (7)0.0348 (3)
O30.47228 (4)0.17883 (14)0.38760 (6)0.0291 (2)
O40.35874 (6)0.47522 (16)0.09223 (7)0.0426 (3)
N10.38713 (7)0.41091 (18)0.49122 (8)0.0345 (3)
N20.32197 (7)0.09884 (19)0.55201 (9)0.0413 (4)
N30.33912 (6)0.61958 (18)0.16513 (8)0.0352 (3)
C10.39214 (6)0.25318 (18)0.47354 (7)0.0230 (3)
C20.37408 (6)0.10514 (18)0.48588 (7)0.0214 (3)
C30.38129 (5)0.06768 (17)0.46095 (7)0.0197 (3)
H30.40130.14380.50380.024*
C40.41822 (5)0.04584 (18)0.43117 (7)0.0203 (3)
C50.43496 (5)0.10712 (18)0.42212 (7)0.0210 (3)
C60.43859 (6)0.19806 (19)0.41517 (8)0.0249 (3)
C70.48778 (6)0.0207 (2)0.37698 (8)0.0266 (3)
C80.52233 (7)0.0159 (2)0.34973 (8)0.0345 (4)
H80.53340.11750.33750.041*
C90.54018 (7)0.1405 (3)0.34089 (9)0.0390 (4)
H90.56420.14580.32300.047*
C100.52348 (7)0.2900 (2)0.35773 (9)0.0368 (4)
H100.53600.39610.35100.044*
C110.48879 (6)0.2849 (2)0.38422 (8)0.0300 (3)
H110.47730.38700.39550.036*
C120.47074 (6)0.1270 (2)0.39422 (7)0.0238 (3)
C130.34544 (6)0.10701 (18)0.52264 (8)0.0268 (3)
C140.32350 (6)0.14503 (17)0.40813 (7)0.0200 (3)
C150.29340 (6)0.10115 (18)0.33595 (7)0.0225 (3)
H150.31030.03160.31740.027*
C160.23851 (6)0.15905 (18)0.29081 (7)0.0232 (3)
C170.21367 (6)0.26033 (18)0.31777 (8)0.0247 (3)
C180.24357 (6)0.30705 (18)0.38934 (8)0.0251 (3)
H180.22680.37800.40750.030*
C190.29853 (6)0.24895 (18)0.43439 (8)0.0229 (3)
H190.31920.28050.48360.027*
C200.32566 (7)0.5477 (2)0.10384 (9)0.0331 (3)
H200.28720.55250.06560.040*
C210.29794 (10)0.7210 (2)0.16975 (13)0.0508 (5)
H21A0.30700.84160.17120.076*
H21B0.29890.69090.21350.076*
H21C0.26020.69880.12770.076*
C220.39687 (10)0.6254 (4)0.22459 (12)0.0648 (6)
H22A0.41920.54320.21680.097*
H22B0.39870.59740.26900.097*
H22C0.41200.73970.22840.097*
H1A0.3999 (8)0.489 (3)0.4773 (11)0.040 (5)*
H1B0.3728 (9)0.431 (3)0.5173 (12)0.047 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0301 (2)0.0458 (2)0.02092 (18)0.00131 (16)0.00693 (15)0.00137 (15)
Cl20.02028 (18)0.0461 (2)0.0367 (2)0.00938 (16)0.01051 (16)0.00872 (17)
O10.0274 (5)0.0220 (5)0.0307 (5)0.0007 (4)0.0187 (5)0.0026 (4)
O20.0420 (7)0.0240 (5)0.0478 (7)0.0013 (5)0.0304 (6)0.0020 (5)
O30.0284 (5)0.0323 (6)0.0320 (6)0.0001 (4)0.0198 (5)0.0029 (5)
O40.0532 (8)0.0433 (7)0.0417 (7)0.0096 (6)0.0323 (6)0.0021 (6)
N10.0476 (9)0.0230 (7)0.0468 (8)0.0026 (6)0.0345 (8)0.0006 (6)
N20.0522 (9)0.0365 (8)0.0560 (9)0.0099 (7)0.0427 (8)0.0097 (7)
N30.0440 (8)0.0323 (7)0.0386 (8)0.0030 (6)0.0283 (7)0.0027 (6)
C10.0206 (7)0.0258 (7)0.0222 (7)0.0009 (5)0.0112 (6)0.0009 (5)
C20.0200 (6)0.0230 (7)0.0210 (6)0.0016 (5)0.0109 (5)0.0015 (5)
C30.0175 (6)0.0211 (6)0.0188 (6)0.0009 (5)0.0087 (5)0.0016 (5)
C40.0152 (6)0.0250 (7)0.0178 (6)0.0001 (5)0.0070 (5)0.0006 (5)
C50.0154 (6)0.0267 (7)0.0174 (6)0.0006 (5)0.0065 (5)0.0014 (5)
C60.0209 (7)0.0287 (8)0.0248 (7)0.0007 (6)0.0120 (6)0.0011 (6)
C70.0201 (7)0.0373 (8)0.0198 (7)0.0030 (6)0.0089 (6)0.0008 (6)
C80.0263 (8)0.0540 (10)0.0256 (8)0.0006 (7)0.0156 (7)0.0027 (7)
C90.0259 (8)0.0686 (12)0.0256 (8)0.0056 (8)0.0160 (7)0.0044 (8)
C100.0277 (8)0.0526 (10)0.0288 (8)0.0087 (7)0.0144 (7)0.0095 (7)
C110.0231 (7)0.0391 (9)0.0244 (7)0.0049 (6)0.0105 (6)0.0046 (6)
C120.0161 (6)0.0345 (8)0.0170 (6)0.0026 (6)0.0064 (5)0.0024 (6)
C130.0282 (7)0.0229 (7)0.0314 (8)0.0044 (6)0.0174 (7)0.0052 (6)
C140.0183 (6)0.0197 (6)0.0221 (6)0.0008 (5)0.0109 (5)0.0016 (5)
C150.0214 (7)0.0237 (7)0.0234 (7)0.0009 (5)0.0127 (6)0.0002 (5)
C160.0224 (7)0.0243 (7)0.0202 (6)0.0017 (5)0.0096 (6)0.0016 (5)
C170.0182 (6)0.0251 (7)0.0291 (7)0.0033 (5)0.0115 (6)0.0072 (6)
C180.0243 (7)0.0238 (7)0.0301 (7)0.0041 (5)0.0164 (6)0.0015 (6)
C190.0229 (7)0.0224 (7)0.0231 (7)0.0001 (5)0.0122 (6)0.0017 (5)
C200.0364 (8)0.0309 (8)0.0346 (8)0.0008 (7)0.0208 (7)0.0022 (7)
C210.0778 (15)0.0329 (9)0.0748 (14)0.0013 (9)0.0629 (13)0.0004 (9)
C220.0594 (14)0.0805 (17)0.0432 (12)0.0116 (12)0.0202 (11)0.0133 (11)
Geometric parameters (Å, º) top
Cl1—C161.7332 (15)C7—C81.392 (2)
Cl2—C171.7349 (14)C8—C91.383 (3)
O1—C51.3583 (17)C8—H80.9500
O1—C11.3784 (17)C9—C101.391 (3)
O2—C61.2091 (19)C9—H90.9500
O3—C71.3815 (19)C10—C111.382 (2)
O3—C61.3830 (17)C10—H100.9500
O4—C201.231 (2)C11—C121.406 (2)
N1—C11.333 (2)C11—H110.9500
N1—H1A0.85 (2)C14—C151.3891 (19)
N1—H1B0.88 (2)C14—C191.3923 (19)
N2—C131.150 (2)C15—C161.390 (2)
N3—C201.322 (2)C15—H150.9500
N3—C221.440 (3)C16—C171.389 (2)
N3—C211.455 (2)C17—C181.384 (2)
C1—C21.357 (2)C18—C191.392 (2)
C2—C131.418 (2)C18—H180.9500
C2—C31.5232 (19)C19—H190.9500
C3—C41.5086 (18)C20—H200.9500
C3—C141.5290 (18)C21—H21A0.9800
C3—H31.0000C21—H21B0.9800
C4—C51.348 (2)C21—H21C0.9800
C4—C61.453 (2)C22—H22A0.9800
C5—C121.4437 (19)C22—H22B0.9800
C7—C121.388 (2)C22—H22C0.9800
C5—O1—C1118.58 (11)C10—C11—C12119.27 (16)
C7—O3—C6121.81 (12)C10—C11—H11120.4
C1—N1—H1A116.0 (13)C12—C11—H11120.4
C1—N1—H1B121.3 (14)C7—C12—C11119.49 (13)
H1A—N1—H1B122.7 (19)C7—C12—C5116.70 (13)
C20—N3—C22120.69 (16)C11—C12—C5123.81 (14)
C20—N3—C21120.42 (16)N2—C13—C2176.18 (16)
C22—N3—C21117.94 (17)C15—C14—C19119.49 (12)
N1—C1—C2129.28 (14)C15—C14—C3121.29 (12)
N1—C1—O1109.24 (13)C19—C14—C3118.95 (12)
C2—C1—O1121.48 (13)C14—C15—C16119.94 (13)
C1—C2—C13119.66 (13)C14—C15—H15120.0
C1—C2—C3124.01 (12)C16—C15—H15120.0
C13—C2—C3116.31 (12)C17—C16—C15120.12 (13)
C4—C3—C2108.20 (11)C17—C16—Cl1120.87 (11)
C4—C3—C14114.29 (11)C15—C16—Cl1118.97 (11)
C2—C3—C14109.82 (11)C18—C17—C16120.42 (13)
C4—C3—H3108.1C18—C17—Cl2119.06 (11)
C2—C3—H3108.1C16—C17—Cl2120.50 (11)
C14—C3—H3108.1C17—C18—C19119.30 (13)
C5—C4—C6119.22 (12)C17—C18—H18120.3
C5—C4—C3122.95 (12)C19—C18—H18120.3
C6—C4—C3117.76 (12)C18—C19—C14120.71 (13)
C4—C5—O1123.99 (12)C18—C19—H19119.6
C4—C5—C12122.64 (13)C14—C19—H19119.6
O1—C5—C12113.37 (12)O4—C20—N3125.44 (16)
O2—C6—O3116.59 (13)O4—C20—H20117.3
O2—C6—C4125.39 (13)N3—C20—H20117.3
O3—C6—C4118.02 (12)N3—C21—H21A109.5
O3—C7—C12121.54 (13)N3—C21—H21B109.5
O3—C7—C8117.10 (14)H21A—C21—H21B109.5
C12—C7—C8121.35 (15)N3—C21—H21C109.5
C9—C8—C7118.43 (16)H21A—C21—H21C109.5
C9—C8—H8120.8H21B—C21—H21C109.5
C7—C8—H8120.8N3—C22—H22A109.5
C8—C9—C10121.10 (15)N3—C22—H22B109.5
C8—C9—H9119.5H22A—C22—H22B109.5
C10—C9—H9119.5N3—C22—H22C109.5
C11—C10—C9120.37 (16)H22A—C22—H22C109.5
C11—C10—H10119.8H22B—C22—H22C109.5
C9—C10—H10119.8
C5—O1—C1—N1173.75 (12)C9—C10—C11—C120.2 (2)
C5—O1—C1—C25.82 (19)O3—C7—C12—C11178.33 (13)
N1—C1—C2—C130.1 (2)C8—C7—C12—C110.2 (2)
O1—C1—C2—C13179.36 (12)O3—C7—C12—C51.5 (2)
N1—C1—C2—C3178.38 (15)C8—C7—C12—C5179.97 (13)
O1—C1—C2—C32.1 (2)C10—C11—C12—C70.4 (2)
C1—C2—C3—C47.97 (18)C10—C11—C12—C5179.42 (13)
C13—C2—C3—C4173.49 (12)C4—C5—C12—C70.2 (2)
C1—C2—C3—C14117.40 (15)O1—C5—C12—C7179.19 (12)
C13—C2—C3—C1461.14 (16)C4—C5—C12—C11179.97 (13)
C2—C3—C4—C56.91 (17)O1—C5—C12—C110.60 (19)
C14—C3—C4—C5115.77 (14)C1—C2—C13—N2180 (100)
C2—C3—C4—C6169.93 (11)C3—C2—C13—N21 (3)
C14—C3—C4—C667.38 (16)C4—C3—C14—C1539.02 (18)
C6—C4—C5—O1176.78 (12)C2—C3—C14—C1582.78 (15)
C3—C4—C5—O10.0 (2)C4—C3—C14—C19147.06 (13)
C6—C4—C5—C122.6 (2)C2—C3—C14—C1991.14 (15)
C3—C4—C5—C12179.40 (12)C19—C14—C15—C160.9 (2)
C1—O1—C5—C46.98 (19)C3—C14—C15—C16172.99 (13)
C1—O1—C5—C12172.45 (11)C14—C15—C16—C170.2 (2)
C7—O3—C6—O2178.02 (13)C14—C15—C16—Cl1178.08 (11)
C7—O3—C6—C41.67 (19)C15—C16—C17—C181.2 (2)
C5—C4—C6—O2176.38 (14)Cl1—C16—C17—C18179.07 (11)
C3—C4—C6—O20.6 (2)C15—C16—C17—Cl2177.55 (11)
C5—C4—C6—O33.28 (19)Cl1—C16—C17—Cl20.33 (18)
C3—C4—C6—O3179.76 (11)C16—C17—C18—C191.1 (2)
C6—O3—C7—C120.7 (2)Cl2—C17—C18—C19177.61 (11)
C6—O3—C7—C8179.27 (13)C17—C18—C19—C140.1 (2)
O3—C7—C8—C9177.75 (13)C15—C14—C19—C180.9 (2)
C12—C7—C8—C90.8 (2)C3—C14—C19—C18173.09 (13)
C7—C8—C9—C100.9 (2)C22—N3—C20—O43.2 (3)
C8—C9—C10—C110.4 (2)C21—N3—C20—O4171.82 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O4i0.88 (2)2.04 (2)2.888 (2)163 (2)
N1—H1A···O2ii0.85 (2)2.20 (2)3.036 (2)169 (2)
C19—H19···O4iii0.952.553.445 (2)158
Symmetry codes: (i) x, y+1, z+1/2; (ii) x, y+1, z; (iii) x, y, z+1/2.
 

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