In the title compound, C
15H
9Cl
2NO
3, the central double bond is
trans configured and the dihedral angle between the two planar fragments of the molecule is 44.53 (4)°. The crystal packing is stabilized by C—H
O and C—H
Cl contacts.
Supporting information
CCDC reference: 636650
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.005 Å
- R factor = 0.037
- wR factor = 0.093
- Data-to-parameter ratio = 12.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 25.10
From the CIF: _reflns_number_total 2313
Count of symmetry unique reflns 1347
Completeness (_total/calc) 171.71%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 966
Fraction of Friedel pairs measured 0.717
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
1 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
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; 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: SHELXL97 and PLATON.
(2E)-1-(2,4-Dichlorophenyl)-3-(4-nitrophenyl)prop-2-en-1-one
top
Crystal data top
C15H9Cl2NO3 | F(000) = 328 |
Mr = 322.13 | Dx = 1.555 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 2996 reflections |
a = 3.7973 (5) Å | θ = 3.1–25.2° |
b = 7.1528 (9) Å | µ = 0.48 mm−1 |
c = 25.336 (3) Å | T = 173 K |
β = 90.386 (11)° | Plate, light yellow |
V = 688.14 (15) Å3 | 0.22 × 0.18 × 0.09 mm |
Z = 2 | |
Data collection top
Stoe IPDSII two-circle diffractometer | 2313 independent reflections |
Radiation source: fine-focus sealed tube | 2046 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ω scans | θmax = 25.1°, θmin = 3.0° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −4→4 |
Tmin = 0.892, Tmax = 0.948 | k = −8→8 |
3300 measured reflections | l = −30→23 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.037 | w = 1/[σ2(Fo2) + (0.0649P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.093 | (Δ/σ)max = 0.001 |
S = 1.00 | Δρmax = 0.21 e Å−3 |
2313 reflections | Δρmin = −0.26 e Å−3 |
191 parameters | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.049 (5) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), with 994 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.03 (8) |
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 | x | y | z | Uiso*/Ueq | |
Cl1 | 0.36714 (19) | 0.35790 (10) | 0.65651 (3) | 0.0344 (2) | |
Cl2 | 0.8776 (2) | −0.08235 (12) | 0.50426 (3) | 0.0401 (2) | |
O1 | 0.3584 (6) | −0.1122 (3) | 0.75563 (9) | 0.0381 (6) | |
N1 | 0.9194 (6) | 0.8624 (4) | 0.93505 (11) | 0.0329 (6) | |
O11 | 1.0964 (8) | 0.9861 (4) | 0.91408 (12) | 0.0514 (7) | |
O12 | 0.8163 (7) | 0.8713 (4) | 0.98071 (10) | 0.0491 (6) | |
C1 | 0.5196 (8) | 0.0176 (4) | 0.73446 (13) | 0.0287 (7) | |
C2 | 0.6443 (8) | 0.1828 (5) | 0.76319 (14) | 0.0312 (7) | |
H2 | 0.7905 | 0.2697 | 0.7453 | 0.037* | |
C3 | 0.5605 (8) | 0.2170 (4) | 0.81397 (12) | 0.0289 (7) | |
H3 | 0.4231 | 0.1254 | 0.8316 | 0.035* | |
C11 | 0.6029 (7) | 0.0007 (4) | 0.67638 (13) | 0.0269 (7) | |
C12 | 0.5507 (7) | 0.1432 (4) | 0.63927 (13) | 0.0259 (6) | |
C13 | 0.6308 (8) | 0.1180 (5) | 0.58628 (14) | 0.0300 (7) | |
H13 | 0.5919 | 0.2155 | 0.5615 | 0.036* | |
C14 | 0.7687 (7) | −0.0527 (5) | 0.57030 (13) | 0.0303 (7) | |
C15 | 0.8199 (8) | −0.1976 (4) | 0.60589 (14) | 0.0335 (8) | |
H15 | 0.9109 | −0.3144 | 0.5945 | 0.040* | |
C16 | 0.7356 (8) | −0.1689 (5) | 0.65861 (13) | 0.0321 (7) | |
H16 | 0.7696 | −0.2679 | 0.6831 | 0.039* | |
C21 | 0.6629 (7) | 0.3827 (4) | 0.84433 (12) | 0.0271 (6) | |
C22 | 0.5884 (7) | 0.3886 (4) | 0.89871 (12) | 0.0284 (6) | |
H22 | 0.4800 | 0.2842 | 0.9151 | 0.034* | |
C23 | 0.6721 (8) | 0.5458 (4) | 0.92853 (14) | 0.0284 (7) | |
H23 | 0.6229 | 0.5500 | 0.9652 | 0.034* | |
C24 | 0.8285 (7) | 0.6959 (4) | 0.90356 (13) | 0.0268 (6) | |
C25 | 0.9075 (8) | 0.6958 (5) | 0.85005 (13) | 0.0300 (7) | |
H25 | 1.0170 | 0.8006 | 0.8340 | 0.036* | |
C26 | 0.8220 (9) | 0.5387 (4) | 0.82080 (14) | 0.0311 (7) | |
H26 | 0.8719 | 0.5363 | 0.7841 | 0.037* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0350 (4) | 0.0283 (4) | 0.0399 (4) | 0.0032 (3) | 0.0019 (3) | −0.0016 (3) |
Cl2 | 0.0421 (4) | 0.0473 (5) | 0.0309 (4) | −0.0044 (3) | 0.0055 (3) | −0.0084 (4) |
O1 | 0.0452 (12) | 0.0360 (13) | 0.0331 (12) | −0.0125 (11) | 0.0042 (10) | 0.0018 (11) |
N1 | 0.0335 (13) | 0.0291 (13) | 0.0362 (16) | −0.0018 (13) | 0.0000 (11) | −0.0049 (14) |
O11 | 0.0639 (16) | 0.0374 (13) | 0.0530 (17) | −0.0190 (13) | 0.0112 (14) | −0.0075 (13) |
O12 | 0.0643 (15) | 0.0483 (15) | 0.0349 (13) | −0.0128 (13) | 0.0105 (12) | −0.0149 (13) |
C1 | 0.0249 (15) | 0.0325 (17) | 0.0286 (17) | −0.0017 (12) | −0.0024 (13) | 0.0003 (14) |
C2 | 0.0286 (15) | 0.0324 (16) | 0.0328 (18) | −0.0048 (13) | 0.0022 (13) | −0.0014 (14) |
C3 | 0.0278 (15) | 0.0320 (16) | 0.0269 (17) | −0.0013 (13) | 0.0002 (12) | 0.0004 (13) |
C11 | 0.0246 (14) | 0.0256 (14) | 0.0303 (17) | −0.0031 (12) | −0.0014 (13) | −0.0029 (13) |
C12 | 0.0216 (13) | 0.0247 (15) | 0.0312 (17) | −0.0044 (11) | −0.0004 (12) | −0.0020 (13) |
C13 | 0.0268 (14) | 0.0306 (15) | 0.0326 (18) | −0.0011 (13) | 0.0001 (12) | 0.0001 (14) |
C14 | 0.0250 (14) | 0.0375 (17) | 0.0283 (16) | −0.0064 (13) | 0.0015 (12) | −0.0056 (14) |
C15 | 0.0344 (17) | 0.0267 (16) | 0.039 (2) | 0.0020 (12) | −0.0013 (15) | −0.0071 (13) |
C16 | 0.0335 (15) | 0.0302 (17) | 0.0326 (18) | 0.0016 (13) | −0.0046 (13) | −0.0006 (14) |
C21 | 0.0253 (13) | 0.0264 (16) | 0.0295 (15) | 0.0011 (12) | 0.0007 (11) | −0.0003 (13) |
C22 | 0.0290 (14) | 0.0301 (17) | 0.0261 (15) | −0.0043 (12) | 0.0017 (11) | 0.0004 (13) |
C23 | 0.0275 (15) | 0.0312 (17) | 0.0266 (16) | 0.0035 (12) | 0.0020 (13) | 0.0011 (13) |
C24 | 0.0231 (14) | 0.0266 (14) | 0.0307 (17) | −0.0003 (12) | −0.0006 (12) | −0.0018 (13) |
C25 | 0.0305 (15) | 0.0288 (15) | 0.0307 (17) | −0.0011 (13) | 0.0026 (13) | 0.0025 (13) |
C26 | 0.0336 (16) | 0.0317 (17) | 0.0281 (17) | −0.0012 (12) | 0.0038 (14) | 0.0014 (14) |
Geometric parameters (Å, º) top
Cl1—C12 | 1.743 (3) | C13—H13 | 0.9500 |
Cl2—C14 | 1.739 (3) | C14—C15 | 1.387 (5) |
O1—C1 | 1.236 (4) | C15—C16 | 1.391 (5) |
N1—O12 | 1.225 (4) | C15—H15 | 0.9500 |
N1—O11 | 1.234 (4) | C16—H16 | 0.9500 |
N1—C24 | 1.473 (4) | C21—C26 | 1.404 (4) |
C1—C2 | 1.465 (4) | C21—C22 | 1.409 (4) |
C1—C11 | 1.512 (5) | C22—C23 | 1.391 (4) |
C2—C3 | 1.349 (5) | C22—H22 | 0.9500 |
C2—H2 | 0.9500 | C23—C24 | 1.382 (4) |
C3—C21 | 1.465 (4) | C23—H23 | 0.9500 |
C3—H3 | 0.9500 | C24—C25 | 1.390 (5) |
C11—C16 | 1.390 (4) | C25—C26 | 1.383 (5) |
C11—C12 | 1.400 (4) | C25—H25 | 0.9500 |
C12—C13 | 1.390 (5) | C26—H26 | 0.9500 |
C13—C14 | 1.389 (5) | | |
| | | |
O12—N1—O11 | 123.2 (3) | C14—C15—C16 | 118.8 (3) |
O12—N1—C24 | 118.6 (3) | C14—C15—H15 | 120.6 |
O11—N1—C24 | 118.2 (3) | C16—C15—H15 | 120.6 |
O1—C1—C2 | 123.3 (3) | C11—C16—C15 | 121.7 (3) |
O1—C1—C11 | 118.0 (3) | C11—C16—H16 | 119.1 |
C2—C1—C11 | 118.6 (3) | C15—C16—H16 | 119.1 |
C3—C2—C1 | 122.8 (3) | C26—C21—C22 | 118.8 (3) |
C3—C2—H2 | 118.6 | C26—C21—C3 | 122.3 (3) |
C1—C2—H2 | 118.6 | C22—C21—C3 | 118.9 (3) |
C2—C3—C21 | 125.7 (3) | C23—C22—C21 | 120.6 (3) |
C2—C3—H3 | 117.1 | C23—C22—H22 | 119.7 |
C21—C3—H3 | 117.1 | C21—C22—H22 | 119.7 |
C16—C11—C12 | 117.9 (3) | C24—C23—C22 | 118.5 (3) |
C16—C11—C1 | 117.6 (3) | C24—C23—H23 | 120.8 |
C12—C11—C1 | 124.5 (3) | C22—C23—H23 | 120.8 |
C13—C12—C11 | 121.5 (3) | C23—C24—C25 | 122.8 (3) |
C13—C12—Cl1 | 116.5 (2) | C23—C24—N1 | 118.7 (3) |
C11—C12—Cl1 | 121.9 (2) | C25—C24—N1 | 118.5 (3) |
C14—C13—C12 | 118.7 (3) | C26—C25—C24 | 118.1 (3) |
C14—C13—H13 | 120.6 | C26—C25—H25 | 120.9 |
C12—C13—H13 | 120.6 | C24—C25—H25 | 120.9 |
C15—C14—C13 | 121.2 (3) | C25—C26—C21 | 121.2 (3) |
C15—C14—Cl2 | 120.1 (2) | C25—C26—H26 | 119.4 |
C13—C14—Cl2 | 118.7 (3) | C21—C26—H26 | 119.4 |
| | | |
O1—C1—C2—C3 | −7.5 (5) | C1—C11—C16—C15 | 180.0 (3) |
C11—C1—C2—C3 | 174.9 (3) | C14—C15—C16—C11 | −0.2 (4) |
C1—C2—C3—C21 | −177.2 (3) | C2—C3—C21—C26 | 9.2 (5) |
O1—C1—C11—C16 | −45.2 (4) | C2—C3—C21—C22 | −173.0 (3) |
C2—C1—C11—C16 | 132.6 (3) | C26—C21—C22—C23 | −0.2 (4) |
O1—C1—C11—C12 | 133.8 (3) | C3—C21—C22—C23 | −178.1 (3) |
C2—C1—C11—C12 | −48.4 (4) | C21—C22—C23—C24 | 0.2 (4) |
C16—C11—C12—C13 | −0.5 (4) | C22—C23—C24—C25 | −0.4 (4) |
C1—C11—C12—C13 | −179.5 (3) | C22—C23—C24—N1 | −179.7 (3) |
C16—C11—C12—Cl1 | 177.0 (2) | O12—N1—C24—C23 | −8.5 (4) |
C1—C11—C12—Cl1 | −2.0 (4) | O11—N1—C24—C23 | 171.4 (3) |
C11—C12—C13—C14 | −0.6 (4) | O12—N1—C24—C25 | 172.2 (3) |
Cl1—C12—C13—C14 | −178.3 (2) | O11—N1—C24—C25 | −7.9 (4) |
C12—C13—C14—C15 | 1.4 (4) | C23—C24—C25—C26 | 0.6 (5) |
C12—C13—C14—Cl2 | −178.6 (2) | N1—C24—C25—C26 | 179.8 (3) |
C13—C14—C15—C16 | −1.0 (4) | C24—C25—C26—C21 | −0.5 (5) |
Cl2—C14—C15—C16 | 179.0 (2) | C22—C21—C26—C25 | 0.4 (4) |
C12—C11—C16—C15 | 0.9 (4) | C3—C21—C26—C25 | 178.2 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···Cl2i | 0.95 | 2.83 | 3.678 (3) | 149 |
C22—H22···O11ii | 0.95 | 2.58 | 3.455 (4) | 153 |
C23—H23···O12iii | 0.95 | 2.51 | 3.216 (4) | 131 |
C25—H25···O1iv | 0.95 | 2.46 | 3.255 (4) | 141 |
Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) x−1, y−1, z; (iii) −x+1, y−1/2, −z+2; (iv) x+1, y+1, z. |