Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802005433/cv6101sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802005433/cv6101Isup2.hkl |
CCDC reference: 185772
Key indicators
- Single-crystal X-ray study
- T = 213 K
- Mean (C-C) = 0.003 Å
- R factor = 0.067
- wR factor = 0.172
- Data-to-parameter ratio = 14.1
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
The title compound was isolated using silica-gel column chromatography from the photoinduced reaction mixtures of 4-nitroaceptophenone with 1,2-diphenylacetylene. Single crystals were obtained by slow evaporation of a chloroform–ethyl acetate (4:1) solution.
The H atoms were located from difference Fourier maps and were refined isotropically, except for atoms H22A, H22B and H22C, which were geometrically attached to their parent C22 atom, with ideal bond lengths and angles, and were treated as riding with C—H distances of 0.96 Å and Uiso(H) = 1.2 Ueq(C).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT and SADABS (Sheldrick, 1996); 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, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
C22H17NO3 | Dx = 1.324 Mg m−3 |
Mr = 343.37 | Melting point: 450(1)K K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 11.6177 (6) Å | Cell parameters from 4602 reflections |
b = 4.6546 (2) Å | θ = 2.6–28.3° |
c = 31.9119 (16) Å | µ = 0.09 mm−1 |
β = 93.047 (1)° | T = 213 K |
V = 1723.22 (14) Å3 | Needle, colorless |
Z = 4 | 0.50 × 0.14 × 0.12 mm |
F(000) = 720 |
Siemens SMART CCD area-detector diffractometer | 2132 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.093 |
Graphite monochromator | θmax = 28.4°, θmin = 2.6° |
Detector resolution: 8.33 pixels mm-1 | h = −12→15 |
ω scans | k = −6→6 |
9733 measured reflections | l = −42→37 |
4139 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.067 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.172 | w = 1/[σ2(Fo2) + (0.0586P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.87 | (Δ/σ)max < 0.001 |
4139 reflections | Δρmax = 0.34 e Å−3 |
293 parameters | Δρmin = −0.33 e Å−3 |
0 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.018 (2) |
C22H17NO3 | V = 1723.22 (14) Å3 |
Mr = 343.37 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.6177 (6) Å | µ = 0.09 mm−1 |
b = 4.6546 (2) Å | T = 213 K |
c = 31.9119 (16) Å | 0.50 × 0.14 × 0.12 mm |
β = 93.047 (1)° |
Siemens SMART CCD area-detector diffractometer | 2132 reflections with I > 2σ(I) |
9733 measured reflections | Rint = 0.093 |
4139 independent reflections |
R[F2 > 2σ(F2)] = 0.067 | 0 restraints |
wR(F2) = 0.172 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.87 | Δρmax = 0.34 e Å−3 |
4139 reflections | Δρmin = −0.33 e Å−3 |
293 parameters |
Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 30 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible. |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.30666 (15) | 0.4023 (4) | 0.09561 (6) | 0.0324 (5) | |
O1 | 0.29918 (15) | 0.5481 (5) | 0.17556 (5) | 0.0634 (7) | |
O2 | 0.27950 (15) | 0.2502 (4) | 0.02778 (5) | 0.0463 (5) | |
O3 | 0.71316 (14) | 1.3093 (4) | 0.12624 (5) | 0.0465 (5) | |
C1 | 0.40055 (18) | 0.5907 (5) | 0.09366 (6) | 0.0281 (5) | |
C2 | 0.45231 (19) | 0.6522 (5) | 0.05651 (7) | 0.0326 (6) | |
C3 | 0.5433 (2) | 0.8433 (5) | 0.05622 (7) | 0.0314 (6) | |
C4 | 0.58543 (17) | 0.9789 (5) | 0.09285 (7) | 0.0270 (5) | |
C5 | 0.53508 (18) | 0.9103 (5) | 0.13019 (7) | 0.0287 (5) | |
C6 | 0.44393 (17) | 0.7167 (5) | 0.13172 (6) | 0.0272 (5) | |
C7 | 0.39519 (19) | 0.6594 (6) | 0.17299 (7) | 0.0366 (6) | |
C8 | 0.46019 (19) | 0.7417 (6) | 0.21260 (7) | 0.0326 (6) | |
C9 | 0.4014 (2) | 0.8888 (7) | 0.24303 (8) | 0.0430 (7) | |
C10 | 0.4582 (2) | 0.9653 (7) | 0.28052 (8) | 0.0512 (8) | |
C11 | 0.5721 (2) | 0.8874 (7) | 0.28854 (8) | 0.0480 (8) | |
C12 | 0.6298 (2) | 0.7332 (6) | 0.25903 (8) | 0.0434 (7) | |
C13 | 0.5748 (2) | 0.6654 (6) | 0.22089 (8) | 0.0379 (6) | |
C14 | 0.25087 (19) | 0.2495 (5) | 0.06431 (7) | 0.0314 (5) | |
C15 | 0.15023 (18) | 0.0776 (5) | 0.07751 (7) | 0.0295 (5) | |
C16 | 0.0960 (2) | −0.0982 (6) | 0.04795 (8) | 0.0416 (7) | |
C17 | 0.0011 (2) | −0.2607 (7) | 0.05771 (8) | 0.0495 (8) | |
C18 | −0.0412 (2) | −0.2448 (6) | 0.09724 (8) | 0.0410 (7) | |
C19 | 0.0119 (2) | −0.0700 (6) | 0.12706 (8) | 0.0419 (7) | |
C20 | 0.1077 (2) | 0.0880 (6) | 0.11737 (8) | 0.0390 (6) | |
C21 | 0.68295 (19) | 1.1879 (5) | 0.09369 (7) | 0.0315 (5) | |
C22 | 0.7426 (2) | 1.2415 (6) | 0.05396 (7) | 0.0444 (7) | |
H22A | 0.8197 | 1.3075 | 0.0607 | 0.067* | |
H22B | 0.7012 | 1.3849 | 0.0376 | 0.067* | |
H22C | 0.7453 | 1.0665 | 0.0381 | 0.067* | |
H5 | 0.5653 (17) | 1.012 (5) | 0.1555 (7) | 0.028 (6)* | |
H11 | 0.613 (2) | 0.938 (6) | 0.3156 (8) | 0.046 (7)* | |
H18 | −0.110 (2) | −0.363 (6) | 0.1054 (8) | 0.055 (8)* | |
H1 | 0.277 (2) | 0.399 (6) | 0.1244 (8) | 0.057 (8)* | |
H10 | 0.415 (2) | 1.074 (6) | 0.3001 (9) | 0.062 (9)* | |
H13 | 0.611 (2) | 0.574 (5) | 0.2011 (7) | 0.041 (7)* | |
H12 | 0.709 (3) | 0.669 (6) | 0.2648 (8) | 0.066 (9)* | |
H2 | 0.4239 (18) | 0.562 (5) | 0.0302 (7) | 0.032 (6)* | |
H20 | 0.141 (2) | 0.208 (6) | 0.1385 (8) | 0.057 (8)* | |
H16 | 0.124 (2) | −0.111 (7) | 0.0189 (9) | 0.071 (9)* | |
H19 | −0.021 (2) | −0.053 (6) | 0.1544 (8) | 0.054 (8)* | |
H3 | 0.5771 (19) | 0.886 (5) | 0.0306 (7) | 0.036 (6)* | |
H17 | −0.036 (2) | −0.369 (6) | 0.0362 (8) | 0.054 (8)* | |
H9 | 0.316 (3) | 0.941 (7) | 0.2367 (9) | 0.083 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0297 (10) | 0.0429 (14) | 0.0248 (10) | −0.0098 (9) | 0.0026 (8) | −0.0005 (9) |
O1 | 0.0419 (10) | 0.116 (2) | 0.0339 (10) | −0.0385 (11) | 0.0114 (8) | −0.0101 (11) |
O2 | 0.0544 (11) | 0.0523 (13) | 0.0333 (9) | −0.0222 (9) | 0.0126 (8) | −0.0100 (8) |
O3 | 0.0496 (11) | 0.0555 (13) | 0.0347 (9) | −0.0206 (9) | 0.0050 (8) | −0.0098 (9) |
C1 | 0.0279 (11) | 0.0298 (14) | 0.0265 (11) | −0.0023 (9) | 0.0019 (9) | 0.0020 (10) |
C2 | 0.0362 (13) | 0.0364 (16) | 0.0252 (11) | −0.0074 (11) | 0.0018 (10) | 0.0001 (11) |
C3 | 0.0365 (12) | 0.0332 (15) | 0.0248 (11) | −0.0052 (10) | 0.0044 (10) | 0.0024 (10) |
C4 | 0.0272 (11) | 0.0270 (13) | 0.0269 (11) | −0.0018 (9) | 0.0024 (9) | 0.0006 (9) |
C5 | 0.0288 (11) | 0.0323 (14) | 0.0250 (11) | −0.0026 (10) | 0.0016 (9) | −0.0020 (10) |
C6 | 0.0258 (11) | 0.0330 (14) | 0.0234 (10) | −0.0013 (9) | 0.0049 (9) | −0.0008 (10) |
C7 | 0.0306 (12) | 0.0502 (18) | 0.0295 (12) | −0.0059 (11) | 0.0073 (10) | 0.0007 (11) |
C8 | 0.0315 (12) | 0.0424 (16) | 0.0245 (11) | −0.0072 (10) | 0.0065 (9) | 0.0022 (11) |
C9 | 0.0338 (13) | 0.062 (2) | 0.0335 (13) | −0.0025 (12) | 0.0062 (11) | −0.0052 (13) |
C10 | 0.0449 (16) | 0.078 (2) | 0.0316 (14) | −0.0044 (15) | 0.0105 (12) | −0.0159 (14) |
C11 | 0.0468 (16) | 0.069 (2) | 0.0279 (13) | −0.0115 (14) | −0.0009 (12) | −0.0015 (13) |
C12 | 0.0375 (14) | 0.0520 (19) | 0.0402 (14) | −0.0039 (12) | −0.0018 (12) | 0.0071 (13) |
C13 | 0.0360 (13) | 0.0446 (17) | 0.0336 (13) | 0.0000 (12) | 0.0073 (11) | −0.0026 (12) |
C14 | 0.0358 (12) | 0.0292 (14) | 0.0297 (12) | −0.0010 (10) | 0.0046 (10) | −0.0012 (10) |
C15 | 0.0318 (12) | 0.0285 (14) | 0.0285 (11) | −0.0022 (9) | 0.0040 (9) | 0.0020 (10) |
C16 | 0.0427 (14) | 0.0476 (18) | 0.0354 (13) | −0.0156 (12) | 0.0110 (11) | −0.0080 (13) |
C17 | 0.0472 (16) | 0.060 (2) | 0.0416 (15) | −0.0256 (14) | 0.0099 (13) | −0.0121 (15) |
C18 | 0.0410 (14) | 0.0427 (17) | 0.0398 (14) | −0.0118 (12) | 0.0077 (12) | 0.0007 (13) |
C19 | 0.0492 (15) | 0.0432 (17) | 0.0342 (13) | −0.0103 (12) | 0.0122 (12) | 0.0011 (12) |
C20 | 0.0444 (14) | 0.0408 (17) | 0.0323 (13) | −0.0142 (12) | 0.0059 (11) | −0.0030 (12) |
C21 | 0.0326 (12) | 0.0320 (15) | 0.0302 (12) | −0.0038 (10) | 0.0041 (10) | −0.0014 (10) |
C22 | 0.0473 (15) | 0.0488 (18) | 0.0380 (14) | −0.0198 (13) | 0.0114 (12) | −0.0032 (12) |
N1—C14 | 1.362 (3) | C10—H10 | 0.97 (3) |
N1—C1 | 1.403 (3) | C11—C12 | 1.385 (4) |
N1—H1 | 1.00 (3) | C11—H11 | 0.99 (2) |
O1—C7 | 1.237 (3) | C12—C13 | 1.381 (3) |
O2—C14 | 1.229 (3) | C12—H12 | 0.98 (3) |
O3—C21 | 1.218 (3) | C13—H13 | 0.88 (2) |
C1—C2 | 1.387 (3) | C14—C15 | 1.496 (3) |
C1—C6 | 1.417 (3) | C15—C16 | 1.376 (3) |
C2—C3 | 1.382 (3) | C15—C20 | 1.390 (3) |
C2—H2 | 0.98 (2) | C16—C17 | 1.386 (3) |
C3—C4 | 1.394 (3) | C16—H16 | 1.00 (3) |
C3—H3 | 0.95 (2) | C17—C18 | 1.380 (3) |
C4—C5 | 1.392 (3) | C17—H17 | 0.94 (3) |
C4—C21 | 1.492 (3) | C18—C19 | 1.373 (3) |
C5—C6 | 1.393 (3) | C18—H18 | 1.02 (3) |
C5—H5 | 0.98 (2) | C19—C20 | 1.382 (3) |
C6—C7 | 1.485 (3) | C19—H19 | 0.98 (2) |
C7—C8 | 1.488 (3) | C20—H20 | 0.94 (3) |
C8—C13 | 1.389 (3) | C21—C22 | 1.498 (3) |
C8—C9 | 1.396 (3) | C22—H22A | 0.9600 |
C9—C10 | 1.381 (3) | C22—H22B | 0.9600 |
C9—H9 | 1.03 (3) | C22—H22C | 0.9600 |
C10—C11 | 1.383 (4) | ||
C14—N1—C1 | 129.38 (18) | C13—C12—C11 | 120.0 (3) |
C14—N1—H1 | 119.7 (16) | C13—C12—H12 | 119.0 (17) |
C1—N1—H1 | 110.8 (16) | C11—C12—H12 | 121.0 (16) |
C2—C1—N1 | 122.7 (2) | C12—C13—C8 | 120.2 (2) |
C2—C1—C6 | 119.8 (2) | C12—C13—H13 | 121.7 (15) |
N1—C1—C6 | 117.54 (18) | C8—C13—H13 | 118.1 (15) |
C3—C2—C1 | 120.4 (2) | O2—C14—N1 | 123.5 (2) |
C3—C2—H2 | 119.5 (13) | O2—C14—C15 | 121.6 (2) |
C1—C2—H2 | 120.1 (13) | N1—C14—C15 | 114.93 (19) |
C2—C3—C4 | 121.3 (2) | C16—C15—C20 | 118.4 (2) |
C2—C3—H3 | 119.5 (14) | C16—C15—C14 | 117.5 (2) |
C4—C3—H3 | 119.1 (14) | C20—C15—C14 | 124.1 (2) |
C5—C4—C3 | 118.0 (2) | C15—C16—C17 | 120.8 (2) |
C5—C4—C21 | 119.17 (19) | C15—C16—H16 | 120.5 (17) |
C3—C4—C21 | 122.83 (19) | C17—C16—H16 | 118.7 (17) |
C4—C5—C6 | 122.2 (2) | C18—C17—C16 | 120.1 (3) |
C4—C5—H5 | 116.3 (12) | C18—C17—H17 | 121.4 (16) |
C6—C5—H5 | 121.4 (12) | C16—C17—H17 | 118.2 (16) |
C5—C6—C1 | 118.30 (19) | C19—C18—C17 | 119.7 (2) |
C5—C6—C7 | 118.3 (2) | C19—C18—H18 | 118.3 (14) |
C1—C6—C7 | 123.4 (2) | C17—C18—H18 | 122.0 (15) |
O1—C7—C6 | 121.4 (2) | C18—C19—C20 | 119.9 (2) |
O1—C7—C8 | 118.07 (19) | C18—C19—H19 | 118.7 (15) |
C6—C7—C8 | 120.47 (19) | C20—C19—H19 | 121.3 (15) |
C13—C8—C9 | 119.5 (2) | C19—C20—C15 | 121.0 (2) |
C13—C8—C7 | 122.3 (2) | C19—C20—H20 | 117.2 (16) |
C9—C8—C7 | 118.2 (2) | C15—C20—H20 | 121.7 (16) |
C10—C9—C8 | 120.0 (2) | O3—C21—C4 | 120.12 (19) |
C10—C9—H9 | 121.2 (17) | O3—C21—C22 | 121.3 (2) |
C8—C9—H9 | 118.8 (17) | C4—C21—C22 | 118.6 (2) |
C9—C10—C11 | 120.0 (3) | C21—C22—H22A | 109.5 |
C9—C10—H10 | 117.2 (16) | C21—C22—H22B | 109.5 |
C11—C10—H10 | 122.8 (16) | H22A—C22—H22B | 109.5 |
C10—C11—C12 | 120.2 (2) | C21—C22—H22C | 109.5 |
C10—C11—H11 | 120.7 (14) | H22A—C22—H22C | 109.5 |
C12—C11—H11 | 119.1 (14) | H22B—C22—H22C | 109.5 |
C14—N1—C1—C2 | 0.5 (4) | C8—C9—C10—C11 | −2.3 (5) |
C14—N1—C1—C6 | −178.4 (2) | C9—C10—C11—C12 | 0.2 (5) |
N1—C1—C2—C3 | 178.9 (2) | C10—C11—C12—C13 | 2.2 (4) |
C6—C1—C2—C3 | −2.2 (4) | C11—C12—C13—C8 | −2.5 (4) |
C1—C2—C3—C4 | −0.1 (4) | C9—C8—C13—C12 | 0.4 (4) |
C2—C3—C4—C5 | 1.8 (4) | C7—C8—C13—C12 | −176.5 (2) |
C2—C3—C4—C21 | −179.6 (2) | C1—N1—C14—O2 | 2.3 (4) |
C3—C4—C5—C6 | −1.2 (4) | C1—N1—C14—C15 | −177.6 (2) |
C21—C4—C5—C6 | −179.9 (2) | O2—C14—C15—C16 | 5.0 (4) |
C4—C5—C6—C1 | −1.1 (3) | N1—C14—C15—C16 | −175.1 (2) |
C4—C5—C6—C7 | −179.4 (2) | O2—C14—C15—C20 | −174.1 (3) |
C2—C1—C6—C5 | 2.8 (3) | N1—C14—C15—C20 | 5.8 (3) |
N1—C1—C6—C5 | −178.3 (2) | C20—C15—C16—C17 | 0.1 (4) |
C2—C1—C6—C7 | −179.0 (2) | C14—C15—C16—C17 | −179.1 (2) |
N1—C1—C6—C7 | 0.0 (3) | C15—C16—C17—C18 | 0.9 (5) |
C5—C6—C7—O1 | 162.4 (3) | C16—C17—C18—C19 | −0.9 (5) |
C1—C6—C7—O1 | −15.8 (4) | C17—C18—C19—C20 | −0.2 (4) |
C5—C6—C7—C8 | −16.2 (3) | C18—C19—C20—C15 | 1.2 (4) |
C1—C6—C7—C8 | 165.6 (2) | C16—C15—C20—C19 | −1.2 (4) |
O1—C7—C8—C13 | 130.8 (3) | C14—C15—C20—C19 | 177.9 (2) |
C6—C7—C8—C13 | −50.6 (4) | C5—C4—C21—O3 | −4.4 (4) |
O1—C7—C8—C9 | −46.1 (4) | C3—C4—C21—O3 | 176.9 (2) |
C6—C7—C8—C9 | 132.5 (3) | C5—C4—C21—C22 | 175.0 (2) |
C13—C8—C9—C10 | 2.0 (4) | C3—C4—C21—C22 | −3.6 (4) |
C7—C8—C9—C10 | 179.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 1.00 (3) | 1.78 (3) | 2.646 (3) | 143 (2) |
C2—H2···O2 | 0.98 (2) | 2.22 (2) | 2.860 (3) | 122 (2) |
C22—H22C···O2i | 0.96 | 2.57 | 3.469 (3) | 156 |
Symmetry code: (i) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C22H17NO3 |
Mr | 343.37 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 213 |
a, b, c (Å) | 11.6177 (6), 4.6546 (2), 31.9119 (16) |
β (°) | 93.047 (1) |
V (Å3) | 1723.22 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.50 × 0.14 × 0.12 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9733, 4139, 2132 |
Rint | 0.093 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.067, 0.172, 0.87 |
No. of reflections | 4139 |
No. of parameters | 293 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.34, −0.33 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT and SADABS (Sheldrick, 1996), SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
N1—C14 | 1.362 (3) | N1—C1 | 1.403 (3) |
C14—N1—C1 | 129.38 (18) | C1—N1—H1 | 110.8 (16) |
C14—N1—H1 | 119.7 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 1.00 (3) | 1.78 (3) | 2.646 (3) | 143 (2) |
C2—H2···O2 | 0.98 (2) | 2.22 (2) | 2.860 (3) | 122 (2) |
C22—H22C···O2i | 0.96 | 2.57 | 3.469 (3) | 156 |
Symmetry code: (i) −x+1, −y+1, −z. |
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Photoinduced electron transfer (PET) reactions of organic compounds have been extensively investigated in recent years (Scheinbaum, 1964; Kavarnos & Turro, 1986; D'Auria et al., 1996). Nitroaromatic compounds have been found to undergo PET reactions with 1,2-diphenylacetylene to give benzenamine derivatives among the other products (Tian & Xu, 2002). The crystal structures of the benzenamine derivatives have also been reported in our previous studies (Usman et al., 2002a,b). In our ongoing study on the PET reactions of nitroaromatic compounds, we have carried out a similar reaction for 4-nitroacetophenone and isolated the title compound, (I), which was structurally analyzed in order to elucidate its conformation.
The bond lengths and angles in (I) are within normal ranges (Allen et al., 1987), and are comparable with those in the related compound 4-acetyl-N,N-dibenzoylphenylamine (Usman et al., 2002b). The N-benzoyl and 4-acetylaniline moieties, corresponding to the two aromatic rings A (C1–C6) and B (C15–C20, and the O2/C14/C15/N1 plane, are nearly planar. The dihedral angles of between A and B, between A and O2/C14/C15/N1, and between B and O2/C14/C15/N1 are 8.6 (1), 3.8 (1), and 5.7 (1)°, respectively.
In the title compound, the acetyl group is twisted out about the C4—C21 bond from the attached phenyl by 4.3 (1)°, indicating that this group is coplanar with the attached aromatic ring A.
Aromatic ring C (C8–C13) of another benzoyl (C7–C13/O1) makes a dihedral angle of 59.2 (1)° with the attached aromatic ring A. The carbonyl group (atoms O1 and C7) of the benzoyl is extremely twisted from the aromatic ring C, with the O1 atom deviating by -0.875 (2) Å, and the O1/C6/C7/C8 plane being twisted by 48.9 (1)°.
There are two intramolecular interactions, N1—H1···O1 and C2—H2···O2 (Fig. 1), forming closed six-membered rings O1—C7—C6—C1—N1—H1 and O2—C14—N1—C1—C2—H2.
In the packing, the molecules are linked by weak C22—H22C···O2i [symmetry code: (i) 1 - x, 1 - y, -z] interactions into dimers which are stacked parallel to the b direction (Fig. 2). The packing is stabilized by this interaction, as -well as by dipole-dipole and van der Waals interactions