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The title compound, C19H12N3O2·C3H7NO, was synthesized by the reaction of 1-(4-chloro­phen­yl)-3-phenyl­prop-2-en-1-one and 6-amino­uracil in the presence of KF–alumina in ethyl alcohol; its crystal structure was determined at low temperature [193 (2) K]. The crystal structure is stabilized by N—H...O, C—H...O and C—H...Cl hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806000110/wn6411sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806000110/wn6411Isup2.hkl
Contains datablock I

CCDC reference: 291527

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.038
  • wR factor = 0.094
  • Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 - C7 .. 5.64 su PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C21 PLAT480_ALERT_4_C Long H...A H-Bond Reported H16 .. CL1 .. 2.86 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

5-(4-Chlorophenyl)-7-phenylpyrido[2,3-d]pyrimidine-1,8-dione dimethylformamide solvate top
Crystal data top
C19H12ClN3O2·C3H7NOZ = 2
Mr = 422.86F(000) = 440
Triclinic, P1Dx = 1.415 Mg m3
Hall symbol: -P 1Melting point = 561–562 K
a = 7.6985 (7) ÅMo Kα radiation, λ = 0.71070 Å
b = 11.7486 (10) ÅCell parameters from 3710 reflections
c = 12.0533 (8) Åθ = 3.0–25.3°
α = 72.813 (7)°µ = 0.23 mm1
β = 72.868 (7)°T = 193 K
γ = 80.952 (8)°Block, yellow
V = 992.34 (14) Å30.52 × 0.31 × 0.17 mm
Data collection top
Rigaku Mercury
diffractometer
3611 independent reflections
Radiation source: fine-focus sealed tube3249 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
Detector resolution: 7.31 pixels mm-1θmax = 25.4°, θmin = 3.0°
ω scansh = 99
Absorption correction: multi-scan
(Jacobson, 1998)
k = 1414
Tmin = 0.892, Tmax = 0.963l = 1214
9845 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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0433P)2 + 0.3685P]
where P = (Fo2 + 2Fc2)/3
3611 reflections(Δ/σ)max < 0.001
282 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.25 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
Cl10.57870 (6)0.95527 (3)0.15544 (4)0.03617 (14)
O10.10252 (16)0.11383 (10)0.11274 (10)0.0322 (3)
O20.13089 (15)0.12178 (9)0.27640 (9)0.0275 (3)
O30.3099 (2)0.35699 (11)0.69366 (11)0.0442 (3)
N10.21692 (16)0.43535 (11)0.01589 (11)0.0209 (3)
N20.15117 (18)0.27352 (11)0.05992 (12)0.0235 (3)
N30.00401 (18)0.11818 (11)0.08356 (11)0.0236 (3)
N40.4391 (2)0.25959 (13)0.54872 (12)0.0328 (3)
C10.14080 (19)0.33150 (13)0.02656 (13)0.0200 (3)
C20.05626 (19)0.27981 (13)0.14822 (13)0.0198 (3)
C30.0590 (2)0.34168 (13)0.23152 (13)0.0213 (3)
C40.1344 (2)0.45117 (13)0.18655 (13)0.0232 (3)
H40.13320.49650.24030.028*
C50.21216 (19)0.49591 (13)0.06327 (13)0.0207 (3)
C60.0853 (2)0.16524 (13)0.03480 (14)0.0239 (3)
C70.0336 (2)0.16887 (13)0.17831 (13)0.0215 (3)
C80.0020 (2)0.29399 (13)0.36496 (13)0.0231 (3)
C90.0675 (2)0.18041 (14)0.42067 (14)0.0271 (3)
H90.13710.12910.37300.033*
C100.0319 (3)0.14159 (15)0.54506 (15)0.0350 (4)
H100.07840.06440.58220.042*
C110.0712 (3)0.21528 (17)0.61498 (15)0.0419 (5)
H110.09570.18900.70020.050*
C120.1385 (3)0.32735 (17)0.56050 (16)0.0416 (5)
H120.21090.37740.60870.050*
C130.1015 (2)0.36754 (15)0.43619 (14)0.0308 (4)
H130.14670.44530.39960.037*
C140.3011 (2)0.61039 (13)0.01195 (13)0.0215 (3)
C150.3047 (2)0.68494 (15)0.08179 (15)0.0320 (4)
H150.24810.66260.16580.038*
C160.3890 (2)0.79098 (15)0.03159 (15)0.0340 (4)
H160.39060.84110.08040.041*
C170.4706 (2)0.82264 (13)0.09039 (14)0.0250 (3)
C180.4695 (2)0.75115 (14)0.16211 (14)0.0272 (4)
H180.52610.77420.24610.033*
C190.3850 (2)0.64539 (14)0.11087 (14)0.0248 (3)
H190.38430.59580.16030.030*
C200.3779 (3)0.26608 (16)0.66121 (15)0.0365 (4)
H200.38700.19450.72250.044*
C210.5190 (3)0.14834 (18)0.51910 (18)0.0468 (5)
H21A0.52270.08570.59320.070*
H21B0.64310.15930.46710.070*
H21C0.44500.12490.47690.070*
C220.4229 (3)0.36358 (17)0.45025 (16)0.0443 (5)
H22A0.32710.35440.41580.066*
H22B0.53920.37150.38810.066*
H22C0.39170.43520.48020.066*
H20.204 (3)0.3098 (17)0.1371 (18)0.037 (5)*
H30.048 (2)0.0478 (18)0.0981 (16)0.034 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0436 (3)0.0215 (2)0.0424 (3)0.01257 (17)0.0070 (2)0.00596 (18)
O10.0480 (7)0.0265 (6)0.0241 (6)0.0136 (5)0.0014 (5)0.0119 (5)
O20.0349 (6)0.0257 (6)0.0198 (6)0.0110 (5)0.0033 (5)0.0020 (5)
O30.0703 (9)0.0307 (7)0.0257 (6)0.0032 (6)0.0014 (6)0.0101 (5)
N10.0258 (7)0.0174 (6)0.0207 (6)0.0031 (5)0.0064 (5)0.0056 (5)
N20.0322 (7)0.0205 (7)0.0180 (7)0.0082 (6)0.0026 (6)0.0063 (5)
N30.0313 (7)0.0187 (7)0.0217 (7)0.0080 (6)0.0049 (6)0.0058 (5)
N40.0397 (8)0.0324 (8)0.0249 (7)0.0024 (6)0.0042 (6)0.0099 (6)
C10.0224 (7)0.0182 (7)0.0200 (7)0.0000 (6)0.0069 (6)0.0058 (6)
C20.0225 (7)0.0177 (7)0.0191 (7)0.0004 (6)0.0060 (6)0.0046 (6)
C30.0242 (7)0.0199 (7)0.0196 (7)0.0000 (6)0.0064 (6)0.0051 (6)
C40.0310 (8)0.0206 (8)0.0204 (8)0.0030 (6)0.0076 (6)0.0075 (6)
C50.0227 (7)0.0188 (7)0.0219 (8)0.0003 (6)0.0082 (6)0.0058 (6)
C60.0284 (8)0.0213 (8)0.0226 (8)0.0050 (6)0.0051 (6)0.0068 (6)
C70.0246 (7)0.0198 (7)0.0209 (8)0.0004 (6)0.0091 (6)0.0042 (6)
C80.0283 (8)0.0232 (8)0.0202 (8)0.0066 (6)0.0075 (6)0.0057 (6)
C90.0341 (9)0.0231 (8)0.0243 (8)0.0048 (7)0.0084 (7)0.0043 (6)
C100.0482 (10)0.0280 (9)0.0274 (9)0.0072 (8)0.0159 (8)0.0029 (7)
C110.0618 (12)0.0423 (11)0.0186 (8)0.0089 (9)0.0090 (8)0.0028 (8)
C120.0598 (12)0.0392 (11)0.0236 (9)0.0023 (9)0.0044 (8)0.0123 (8)
C130.0425 (10)0.0258 (8)0.0229 (8)0.0031 (7)0.0063 (7)0.0066 (7)
C140.0243 (7)0.0182 (7)0.0234 (8)0.0007 (6)0.0085 (6)0.0059 (6)
C150.0473 (10)0.0273 (9)0.0223 (8)0.0116 (8)0.0037 (7)0.0088 (7)
C160.0479 (10)0.0273 (9)0.0316 (9)0.0113 (8)0.0074 (8)0.0136 (7)
C170.0276 (8)0.0168 (7)0.0306 (8)0.0041 (6)0.0084 (7)0.0043 (6)
C180.0314 (8)0.0248 (8)0.0240 (8)0.0051 (7)0.0055 (7)0.0045 (7)
C190.0320 (8)0.0219 (8)0.0229 (8)0.0038 (6)0.0078 (7)0.0081 (6)
C200.0464 (10)0.0323 (10)0.0252 (9)0.0054 (8)0.0023 (8)0.0052 (7)
C210.0552 (12)0.0445 (11)0.0384 (11)0.0079 (9)0.0057 (9)0.0202 (9)
C220.0641 (13)0.0416 (11)0.0261 (9)0.0087 (9)0.0098 (9)0.0069 (8)
Geometric parameters (Å, º) top
Cl1—C171.7426 (15)C9—H90.9500
O1—C61.2254 (18)C10—C111.383 (3)
O2—C71.2193 (18)C10—H100.9500
O3—C201.232 (2)C11—C121.381 (3)
N1—C11.3316 (19)C11—H110.9500
N1—C51.3380 (19)C12—C131.386 (2)
N2—C61.3610 (19)C12—H120.9500
N2—C11.3822 (19)C13—H130.9500
N2—H20.90 (2)C14—C151.391 (2)
N3—C61.3745 (19)C14—C191.392 (2)
N3—C71.3845 (19)C15—C161.385 (2)
N3—H30.89 (2)C15—H150.9500
N4—C201.319 (2)C16—C171.379 (2)
N4—C221.449 (2)C16—H160.9500
N4—C211.452 (2)C17—C181.374 (2)
C1—C21.407 (2)C18—C191.383 (2)
C2—C31.409 (2)C18—H180.9500
C2—C71.472 (2)C19—H190.9500
C3—C41.387 (2)C20—H200.9500
C3—C81.491 (2)C21—H21A0.9800
C4—C51.399 (2)C21—H21B0.9800
C4—H40.9500C21—H21C0.9800
C5—C141.486 (2)C22—H22A0.9800
C8—C131.392 (2)C22—H22B0.9800
C8—C91.394 (2)C22—H22C0.9800
C9—C101.387 (2)
C1—N1—C5117.53 (12)C12—C11—H11120.1
C6—N2—C1123.66 (13)C10—C11—H11120.1
C6—N2—H2118.5 (12)C11—C12—C13120.70 (17)
C1—N2—H2117.8 (12)C11—C12—H12119.7
C6—N3—C7127.16 (13)C13—C12—H12119.7
C6—N3—H3114.2 (12)C12—C13—C8120.00 (16)
C7—N3—H3118.6 (12)C12—C13—H13120.0
C20—N4—C22120.57 (15)C8—C13—H13120.0
C20—N4—C21121.68 (15)C15—C14—C19118.03 (14)
C22—N4—C21117.72 (15)C15—C14—C5122.68 (14)
N1—C1—N2114.50 (13)C19—C14—C5119.29 (13)
N1—C1—C2125.28 (13)C16—C15—C14121.44 (15)
N2—C1—C2120.22 (13)C16—C15—H15119.3
C1—C2—C3116.75 (13)C14—C15—H15119.3
C1—C2—C7118.10 (13)C17—C16—C15118.84 (15)
C3—C2—C7125.11 (13)C17—C16—H16120.6
C4—C3—C2117.67 (13)C15—C16—H16120.6
C4—C3—C8117.08 (13)C18—C17—C16121.27 (14)
C2—C3—C8125.03 (13)C18—C17—Cl1119.07 (12)
C3—C4—C5121.03 (14)C16—C17—Cl1119.67 (12)
C3—C4—H4119.5C17—C18—C19119.34 (14)
C5—C4—H4119.5C17—C18—H18120.3
N1—C5—C4121.64 (13)C19—C18—H18120.3
N1—C5—C14115.59 (13)C18—C19—C14121.09 (14)
C4—C5—C14122.73 (13)C18—C19—H19119.5
O1—C6—N2122.24 (14)C14—C19—H19119.5
O1—C6—N3122.25 (13)O3—C20—N4125.61 (17)
N2—C6—N3115.50 (13)O3—C20—H20117.2
O2—C7—N3119.49 (13)N4—C20—H20117.2
O2—C7—C2125.67 (13)N4—C21—H21A109.5
N3—C7—C2114.83 (13)N4—C21—H21B109.5
C13—C8—C9118.96 (14)H21A—C21—H21B109.5
C13—C8—C3119.98 (13)N4—C21—H21C109.5
C9—C8—C3120.69 (14)H21A—C21—H21C109.5
C10—C9—C8120.63 (16)H21B—C21—H21C109.5
C10—C9—H9119.7N4—C22—H22A109.5
C8—C9—H9119.7N4—C22—H22B109.5
C11—C10—C9119.94 (16)H22A—C22—H22B109.5
C11—C10—H10120.0N4—C22—H22C109.5
C9—C10—H10120.0H22A—C22—H22C109.5
C12—C11—C10119.76 (16)H22B—C22—H22C109.5
C5—N1—C1—N2179.77 (13)C4—C3—C8—C1347.7 (2)
C5—N1—C1—C20.3 (2)C2—C3—C8—C13137.94 (16)
C6—N2—C1—N1178.53 (13)C4—C3—C8—C9125.31 (16)
C6—N2—C1—C21.0 (2)C2—C3—C8—C949.1 (2)
N1—C1—C2—C32.4 (2)C13—C8—C9—C100.7 (2)
N2—C1—C2—C3177.03 (13)C3—C8—C9—C10172.33 (15)
N1—C1—C2—C7175.32 (13)C8—C9—C10—C110.8 (3)
N2—C1—C2—C75.2 (2)C9—C10—C11—C120.0 (3)
C1—C2—C3—C43.8 (2)C10—C11—C12—C131.0 (3)
C7—C2—C3—C4173.76 (14)C11—C12—C13—C81.1 (3)
C1—C2—C3—C8170.58 (14)C9—C8—C13—C120.2 (2)
C7—C2—C3—C811.9 (2)C3—C8—C13—C12173.31 (16)
C2—C3—C4—C52.8 (2)N1—C5—C14—C15178.70 (15)
C8—C3—C4—C5172.03 (13)C4—C5—C14—C153.7 (2)
C1—N1—C5—C41.5 (2)N1—C5—C14—C191.5 (2)
C1—N1—C5—C14179.18 (12)C4—C5—C14—C19176.15 (14)
C3—C4—C5—N10.0 (2)C19—C14—C15—C160.0 (3)
C3—C4—C5—C14177.43 (13)C5—C14—C15—C16179.82 (15)
C1—N2—C6—O1177.17 (14)C14—C15—C16—C170.1 (3)
C1—N2—C6—N33.7 (2)C15—C16—C17—C180.0 (3)
C7—N3—C6—O1179.05 (15)C15—C16—C17—Cl1179.62 (14)
C7—N3—C6—N20.1 (2)C16—C17—C18—C190.1 (2)
C6—N3—C7—O2172.80 (14)Cl1—C17—C18—C19179.54 (12)
C6—N3—C7—C26.0 (2)C17—C18—C19—C140.1 (2)
C1—C2—C7—O2170.45 (14)C15—C14—C19—C180.1 (2)
C3—C2—C7—O27.1 (2)C5—C14—C19—C18179.91 (14)
C1—C2—C7—N38.22 (19)C22—N4—C20—O32.6 (3)
C3—C2—C7—N3174.27 (13)C21—N4—C20—O3179.34 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O3i0.90 (2)1.90 (2)2.7918 (18)168.2 (18)
N3—H3···O1ii0.89 (2)1.95 (2)2.8381 (17)169.8 (17)
C10—H10···O2iii0.952.403.328 (2)164
C13—H13···O3iv0.952.573.514 (2)172
C20—H20···O1v0.952.573.167 (2)121
C21—H21B···O2vi0.982.553.399 (2)145
C16—H16···Cl1vii0.952.863.7763 (17)162
Symmetry codes: (i) x, y, z1; (ii) x, y, z; (iii) x, y, z+1; (iv) x, y+1, z+1; (v) x, y, z+1; (vi) x+1, y, z; (vii) x+1, y+2, z.
 

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