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The title compound, C21H16ClNO, has been synthesized by the condensation reaction of dibenzoyl­methane and 2-chloro­aniline in the presence of p-TsOH. The enaminone structure is stabilized by a strong intra­molecular N—H...O=C hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805032836/dn6261sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805032836/dn6261Isup2.hkl
Contains datablock I

CCDC reference: 289716

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.053
  • wR factor = 0.186
  • Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.97 Deg.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 0 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 0 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003)); software used to prepare material for publication: PLATON.

3-[(2-Chlorophenyl)amino]-1,3-diphenylprop-2-en-1-one top
Crystal data top
C21H16ClNOZ = 2
Mr = 333.80F(000) = 348
Triclinic, P1Dx = 1.277 Mg m3
a = 8.7720 (18) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.7380 (19) ÅCell parameters from 25 reflections
c = 11.306 (2) Åθ = 10–12°
α = 86.02 (3)°µ = 0.23 mm1
β = 74.08 (3)°T = 295 K
γ = 69.26 (3)°Block, yellow
V = 868.1 (4) Å30.40 × 0.30 × 0.20 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
2235 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 25.0°, θmin = 2.2°
ω/2θ scansh = 010
Absorption correction: empirical (using intensity measurements)
ψ scan (North et al., 1968)
k = 1011
Tmin = 0.915, Tmax = 0.947l = 1213
3273 measured reflections3 standard reflections every 200 reflections
3058 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H-atom parameters constrained
wR(F2) = 0.186 w = 1/[σ2(Fo2) + (0.114P)2 + 0.0942P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
3058 reflectionsΔρmax = 0.31 e Å3
218 parametersΔρmin = 0.33 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.055 (10)
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
Cl0.15838 (11)0.63052 (8)0.41744 (8)0.0744 (3)
O0.3876 (2)0.9311 (2)0.24755 (16)0.0575 (5)
N0.2946 (3)0.8475 (2)0.47807 (19)0.0527 (6)
H1n0.31300.82790.40130.063*
C20.1845 (5)1.4299 (4)0.1502 (3)0.0871 (11)
H20.09411.51840.16760.104*
C30.3095 (5)1.4102 (4)0.0432 (3)0.0837 (11)
H30.30501.48640.01150.100*
C40.4410 (5)1.2801 (4)0.0156 (3)0.0802 (10)
H40.52611.26830.05730.096*
C50.4481 (4)1.1652 (3)0.0960 (2)0.0635 (8)
H50.53641.07560.07600.076*
C60.3236 (3)1.1838 (3)0.2061 (2)0.0511 (6)
C10.1929 (4)1.3176 (3)0.2325 (3)0.0711 (8)
H10.10951.33210.30670.085*
C70.3308 (3)1.0591 (3)0.2918 (2)0.0480 (6)
C80.2702 (3)1.0923 (3)0.4213 (2)0.0491 (6)
H80.23941.18920.44730.059*
C90.2546 (3)0.9904 (3)0.5093 (2)0.0474 (6)
C100.1802 (3)1.0386 (3)0.6410 (2)0.0467 (6)
C110.2466 (3)1.1189 (3)0.6964 (2)0.0532 (7)
H110.34111.14040.65160.064*
C120.1729 (4)1.1667 (3)0.8175 (3)0.0664 (8)
H120.22001.21740.85500.080*
C130.0293 (4)1.1394 (4)0.8833 (3)0.0705 (8)
H130.02211.17410.96440.085*
C140.0380 (4)1.0603 (4)0.8286 (3)0.0692 (8)
H140.13481.04200.87290.083*
C150.0372 (3)1.0088 (3)0.7092 (2)0.0578 (7)
H150.00720.95390.67350.069*
C160.3095 (3)0.7274 (3)0.5564 (2)0.0477 (6)
C170.3875 (4)0.7111 (3)0.6509 (2)0.0570 (7)
H170.42730.78330.66550.068*
C180.4065 (4)0.5898 (3)0.7232 (3)0.0654 (8)
H180.45810.58080.78640.079*
C190.3487 (4)0.4812 (3)0.7018 (3)0.0701 (9)
H190.36050.39970.75120.084*
C200.2742 (4)0.4938 (3)0.6075 (3)0.0643 (8)
H200.23730.42000.59220.077*
C210.2539 (3)0.6160 (3)0.5354 (2)0.0524 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0773 (6)0.0678 (5)0.0927 (6)0.0267 (4)0.0428 (5)0.0016 (4)
O0.0583 (11)0.0543 (11)0.0626 (11)0.0236 (9)0.0146 (9)0.0010 (9)
N0.0633 (14)0.0496 (12)0.0521 (12)0.0264 (10)0.0187 (10)0.0076 (9)
C20.110 (3)0.068 (2)0.067 (2)0.014 (2)0.023 (2)0.0115 (16)
C30.131 (3)0.073 (2)0.0522 (18)0.043 (2)0.027 (2)0.0200 (16)
C40.106 (3)0.091 (3)0.0473 (16)0.051 (2)0.0069 (17)0.0080 (16)
C50.0722 (19)0.0666 (18)0.0531 (15)0.0299 (15)0.0114 (14)0.0018 (13)
C60.0531 (15)0.0558 (15)0.0510 (14)0.0257 (12)0.0157 (12)0.0030 (11)
C10.076 (2)0.0683 (19)0.0571 (17)0.0173 (16)0.0113 (15)0.0120 (14)
C70.0394 (13)0.0551 (15)0.0565 (15)0.0231 (11)0.0158 (11)0.0048 (12)
C80.0492 (14)0.0470 (14)0.0546 (14)0.0225 (11)0.0127 (11)0.0054 (11)
C90.0401 (13)0.0537 (14)0.0544 (14)0.0215 (11)0.0166 (11)0.0067 (11)
C100.0421 (13)0.0461 (13)0.0550 (14)0.0167 (11)0.0185 (11)0.0113 (11)
C110.0536 (15)0.0494 (14)0.0632 (16)0.0235 (12)0.0207 (13)0.0105 (12)
C120.088 (2)0.0556 (16)0.0667 (18)0.0317 (16)0.0311 (17)0.0057 (13)
C130.077 (2)0.0701 (19)0.0536 (16)0.0160 (16)0.0143 (15)0.0060 (14)
C140.0575 (17)0.083 (2)0.0644 (18)0.0281 (16)0.0102 (14)0.0134 (15)
C150.0485 (15)0.0723 (18)0.0594 (16)0.0288 (14)0.0168 (13)0.0092 (13)
C160.0415 (13)0.0466 (13)0.0552 (14)0.0173 (11)0.0118 (11)0.0062 (11)
C170.0614 (16)0.0577 (16)0.0621 (16)0.0295 (13)0.0228 (13)0.0084 (13)
C180.073 (2)0.0648 (18)0.0640 (17)0.0245 (15)0.0289 (15)0.0125 (14)
C190.084 (2)0.0543 (17)0.0682 (18)0.0265 (16)0.0162 (16)0.0182 (14)
C200.0654 (18)0.0496 (16)0.0783 (19)0.0249 (14)0.0142 (15)0.0045 (14)
C210.0466 (14)0.0494 (14)0.0613 (15)0.0168 (11)0.0141 (12)0.0001 (12)
Geometric parameters (Å, º) top
O—C71.250 (3)C10—C151.396 (4)
N—C91.356 (3)C11—C121.378 (4)
N—C161.407 (3)C11—H110.9300
N—H1n0.8600C12—C131.381 (5)
C2—C31.363 (5)C12—H120.9300
C2—C11.381 (4)C13—C141.383 (4)
C2—H20.9300C13—H130.9300
C3—C41.361 (5)C14—C151.371 (4)
C3—H30.9300C14—H140.9300
C4—C51.386 (4)C15—H150.9300
C4—H40.9300C16—C171.392 (3)
C5—C61.386 (4)C16—C211.394 (4)
C5—H50.9300C17—C181.375 (4)
C6—C11.381 (4)C17—H170.9300
C6—C71.495 (4)C18—C191.384 (4)
C1—H10.9300C18—H180.9300
C7—C81.431 (4)C19—C201.373 (4)
C8—C91.371 (3)C19—H190.9300
C8—H80.9300C20—C211.380 (4)
C9—C101.487 (4)C20—H200.9300
C10—C111.390 (3)Cl—C211.733 (3)
C9—N—C16127.7 (2)C12—C11—C10120.2 (3)
C9—N—H1n116.2C12—C11—H11119.9
C16—N—H1n116.2C10—C11—H11119.9
C3—C2—C1119.6 (3)C11—C12—C13120.2 (3)
C3—C2—H2120.2C11—C12—H12119.9
C1—C2—H2120.2C13—C12—H12119.9
C4—C3—C2120.8 (3)C12—C13—C14119.9 (3)
C4—C3—H3119.6C12—C13—H13120.1
C2—C3—H3119.6C14—C13—H13120.1
C3—C4—C5120.1 (3)C15—C14—C13120.3 (3)
C3—C4—H4119.9C15—C14—H14119.8
C5—C4—H4119.9C13—C14—H14119.8
C6—C5—C4120.0 (3)C14—C15—C10120.2 (3)
C6—C5—H5120.0C14—C15—H15119.9
C4—C5—H5120.0C10—C15—H15119.9
C1—C6—C5118.6 (3)C17—C16—C21118.2 (2)
C1—C6—C7121.5 (2)C17—C16—N122.0 (2)
C5—C6—C7119.8 (2)C21—C16—N119.7 (2)
C2—C1—C6120.8 (3)C18—C17—C16120.9 (3)
C2—C1—H1119.6C18—C17—H17119.5
C6—C1—H1119.6C16—C17—H17119.5
O—C7—C6118.8 (2)C17—C18—C19120.0 (3)
O—C7—C8123.0 (2)C17—C18—H18120.0
C6—C7—C8118.2 (2)C19—C18—H18120.0
C7—C8—C9124.2 (2)C20—C19—C18120.0 (3)
C9—C8—H8117.9C20—C19—H19120.0
C7—C8—H8117.9C18—C19—H19120.0
N—C9—C8121.2 (2)C19—C20—C21120.1 (3)
N—C9—C10119.0 (2)C19—C20—H20119.9
C8—C9—C10119.6 (2)C21—C20—H20119.9
C11—C10—C15119.1 (2)C20—C21—C16120.8 (3)
C11—C10—C9120.9 (2)C20—C21—Cl119.4 (2)
C15—C10—C9119.8 (2)C16—C21—Cl119.8 (2)
C1—C2—C3—C41.2 (6)C15—C10—C11—C120.7 (4)
C2—C3—C4—C50.6 (6)C9—C10—C11—C12178.0 (2)
C3—C4—C5—C61.6 (5)C10—C11—C12—C132.2 (4)
C4—C5—C6—C10.8 (4)C11—C12—C13—C141.8 (5)
C4—C5—C6—C7179.3 (3)C12—C13—C14—C150.0 (5)
C3—C2—C1—C62.0 (6)C13—C14—C15—C101.5 (4)
C5—C6—C1—C21.0 (5)C11—C10—C15—C141.1 (4)
C7—C6—C1—C2177.4 (3)C9—C10—C15—C14176.2 (3)
C1—C6—C7—O144.2 (3)C9—N—C16—C1741.5 (4)
C5—C6—C7—O34.2 (3)C9—N—C16—C21142.3 (3)
C1—C6—C7—C835.2 (4)C21—C16—C17—C181.1 (4)
C5—C6—C7—C8146.4 (3)N—C16—C17—C18177.4 (3)
O—C7—C8—C95.7 (4)C16—C17—C18—C190.5 (5)
C6—C7—C8—C9173.6 (2)C17—C18—C19—C200.7 (5)
C16—N—C9—C8169.7 (2)C18—C19—C20—C211.2 (5)
C16—N—C9—C1015.0 (4)C19—C20—C21—C160.5 (4)
C7—C8—C9—N1.0 (4)C19—C20—C21—Cl179.6 (2)
C7—C8—C9—C10176.3 (2)C17—C16—C21—C200.7 (4)
N—C9—C10—C11129.5 (3)N—C16—C21—C20177.0 (2)
C8—C9—C10—C1155.1 (3)C17—C16—C21—Cl179.2 (2)
N—C9—C10—C1553.2 (3)N—C16—C21—Cl2.9 (3)
C8—C9—C10—C15122.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N—H1n···O0.862.012.670 (3)132
 

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