Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
In the title compound, C15H9Cl2NO3, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806055073/hb2244sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806055073/hb2244Isup2.hkl
Contains datablock I

CCDC reference: 636650

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](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

Computing details top

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
C15H9Cl2NO3F(000) = 328
Mr = 322.13Dx = 1.555 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2996 reflections
a = 3.7973 (5) Åθ = 3.1–25.2°
b = 7.1528 (9) ŵ = 0.48 mm1
c = 25.336 (3) ÅT = 173 K
β = 90.386 (11)°Plate, light yellow
V = 688.14 (15) Å30.22 × 0.18 × 0.09 mm
Z = 2
Data collection top
Stoe IPDSII two-circle
diffractometer
2313 independent reflections
Radiation source: fine-focus sealed tube2046 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ω scansθmax = 25.1°, θmin = 3.0°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 44
Tmin = 0.892, Tmax = 0.948k = 88
3300 measured reflectionsl = 3023
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.00Δρmax = 0.21 e Å3
2313 reflectionsΔρmin = 0.26 e Å3
191 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.049 (5)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), with 994 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute 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
xyzUiso*/Ueq
Cl10.36714 (19)0.35790 (10)0.65651 (3)0.0344 (2)
Cl20.8776 (2)0.08235 (12)0.50426 (3)0.0401 (2)
O10.3584 (6)0.1122 (3)0.75563 (9)0.0381 (6)
N10.9194 (6)0.8624 (4)0.93505 (11)0.0329 (6)
O111.0964 (8)0.9861 (4)0.91408 (12)0.0514 (7)
O120.8163 (7)0.8713 (4)0.98071 (10)0.0491 (6)
C10.5196 (8)0.0176 (4)0.73446 (13)0.0287 (7)
C20.6443 (8)0.1828 (5)0.76319 (14)0.0312 (7)
H20.79050.26970.74530.037*
C30.5605 (8)0.2170 (4)0.81397 (12)0.0289 (7)
H30.42310.12540.83160.035*
C110.6029 (7)0.0007 (4)0.67638 (13)0.0269 (7)
C120.5507 (7)0.1432 (4)0.63927 (13)0.0259 (6)
C130.6308 (8)0.1180 (5)0.58628 (14)0.0300 (7)
H130.59190.21550.56150.036*
C140.7687 (7)0.0527 (5)0.57030 (13)0.0303 (7)
C150.8199 (8)0.1976 (4)0.60589 (14)0.0335 (8)
H150.91090.31440.59450.040*
C160.7356 (8)0.1689 (5)0.65861 (13)0.0321 (7)
H160.76960.26790.68310.039*
C210.6629 (7)0.3827 (4)0.84433 (12)0.0271 (6)
C220.5884 (7)0.3886 (4)0.89871 (12)0.0284 (6)
H220.48000.28420.91510.034*
C230.6721 (8)0.5458 (4)0.92853 (14)0.0284 (7)
H230.62290.55000.96520.034*
C240.8285 (7)0.6959 (4)0.90356 (13)0.0268 (6)
C250.9075 (8)0.6958 (5)0.85005 (13)0.0300 (7)
H251.01700.80060.83400.036*
C260.8220 (9)0.5387 (4)0.82080 (14)0.0311 (7)
H260.87190.53630.78410.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0350 (4)0.0283 (4)0.0399 (4)0.0032 (3)0.0019 (3)0.0016 (3)
Cl20.0421 (4)0.0473 (5)0.0309 (4)0.0044 (3)0.0055 (3)0.0084 (4)
O10.0452 (12)0.0360 (13)0.0331 (12)0.0125 (11)0.0042 (10)0.0018 (11)
N10.0335 (13)0.0291 (13)0.0362 (16)0.0018 (13)0.0000 (11)0.0049 (14)
O110.0639 (16)0.0374 (13)0.0530 (17)0.0190 (13)0.0112 (14)0.0075 (13)
O120.0643 (15)0.0483 (15)0.0349 (13)0.0128 (13)0.0105 (12)0.0149 (13)
C10.0249 (15)0.0325 (17)0.0286 (17)0.0017 (12)0.0024 (13)0.0003 (14)
C20.0286 (15)0.0324 (16)0.0328 (18)0.0048 (13)0.0022 (13)0.0014 (14)
C30.0278 (15)0.0320 (16)0.0269 (17)0.0013 (13)0.0002 (12)0.0004 (13)
C110.0246 (14)0.0256 (14)0.0303 (17)0.0031 (12)0.0014 (13)0.0029 (13)
C120.0216 (13)0.0247 (15)0.0312 (17)0.0044 (11)0.0004 (12)0.0020 (13)
C130.0268 (14)0.0306 (15)0.0326 (18)0.0011 (13)0.0001 (12)0.0001 (14)
C140.0250 (14)0.0375 (17)0.0283 (16)0.0064 (13)0.0015 (12)0.0056 (14)
C150.0344 (17)0.0267 (16)0.039 (2)0.0020 (12)0.0013 (15)0.0071 (13)
C160.0335 (15)0.0302 (17)0.0326 (18)0.0016 (13)0.0046 (13)0.0006 (14)
C210.0253 (13)0.0264 (16)0.0295 (15)0.0011 (12)0.0007 (11)0.0003 (13)
C220.0290 (14)0.0301 (17)0.0261 (15)0.0043 (12)0.0017 (11)0.0004 (13)
C230.0275 (15)0.0312 (17)0.0266 (16)0.0035 (12)0.0020 (13)0.0011 (13)
C240.0231 (14)0.0266 (14)0.0307 (17)0.0003 (12)0.0006 (12)0.0018 (13)
C250.0305 (15)0.0288 (15)0.0307 (17)0.0011 (13)0.0026 (13)0.0025 (13)
C260.0336 (16)0.0317 (17)0.0281 (17)0.0012 (12)0.0038 (14)0.0014 (14)
Geometric parameters (Å, º) top
Cl1—C121.743 (3)C13—H130.9500
Cl2—C141.739 (3)C14—C151.387 (5)
O1—C11.236 (4)C15—C161.391 (5)
N1—O121.225 (4)C15—H150.9500
N1—O111.234 (4)C16—H160.9500
N1—C241.473 (4)C21—C261.404 (4)
C1—C21.465 (4)C21—C221.409 (4)
C1—C111.512 (5)C22—C231.391 (4)
C2—C31.349 (5)C22—H220.9500
C2—H20.9500C23—C241.382 (4)
C3—C211.465 (4)C23—H230.9500
C3—H30.9500C24—C251.390 (5)
C11—C161.390 (4)C25—C261.383 (5)
C11—C121.400 (4)C25—H250.9500
C12—C131.390 (5)C26—H260.9500
C13—C141.389 (5)
O12—N1—O11123.2 (3)C14—C15—C16118.8 (3)
O12—N1—C24118.6 (3)C14—C15—H15120.6
O11—N1—C24118.2 (3)C16—C15—H15120.6
O1—C1—C2123.3 (3)C11—C16—C15121.7 (3)
O1—C1—C11118.0 (3)C11—C16—H16119.1
C2—C1—C11118.6 (3)C15—C16—H16119.1
C3—C2—C1122.8 (3)C26—C21—C22118.8 (3)
C3—C2—H2118.6C26—C21—C3122.3 (3)
C1—C2—H2118.6C22—C21—C3118.9 (3)
C2—C3—C21125.7 (3)C23—C22—C21120.6 (3)
C2—C3—H3117.1C23—C22—H22119.7
C21—C3—H3117.1C21—C22—H22119.7
C16—C11—C12117.9 (3)C24—C23—C22118.5 (3)
C16—C11—C1117.6 (3)C24—C23—H23120.8
C12—C11—C1124.5 (3)C22—C23—H23120.8
C13—C12—C11121.5 (3)C23—C24—C25122.8 (3)
C13—C12—Cl1116.5 (2)C23—C24—N1118.7 (3)
C11—C12—Cl1121.9 (2)C25—C24—N1118.5 (3)
C14—C13—C12118.7 (3)C26—C25—C24118.1 (3)
C14—C13—H13120.6C26—C25—H25120.9
C12—C13—H13120.6C24—C25—H25120.9
C15—C14—C13121.2 (3)C25—C26—C21121.2 (3)
C15—C14—Cl2120.1 (2)C25—C26—H26119.4
C13—C14—Cl2118.7 (3)C21—C26—H26119.4
O1—C1—C2—C37.5 (5)C1—C11—C16—C15180.0 (3)
C11—C1—C2—C3174.9 (3)C14—C15—C16—C110.2 (4)
C1—C2—C3—C21177.2 (3)C2—C3—C21—C269.2 (5)
O1—C1—C11—C1645.2 (4)C2—C3—C21—C22173.0 (3)
C2—C1—C11—C16132.6 (3)C26—C21—C22—C230.2 (4)
O1—C1—C11—C12133.8 (3)C3—C21—C22—C23178.1 (3)
C2—C1—C11—C1248.4 (4)C21—C22—C23—C240.2 (4)
C16—C11—C12—C130.5 (4)C22—C23—C24—C250.4 (4)
C1—C11—C12—C13179.5 (3)C22—C23—C24—N1179.7 (3)
C16—C11—C12—Cl1177.0 (2)O12—N1—C24—C238.5 (4)
C1—C11—C12—Cl12.0 (4)O11—N1—C24—C23171.4 (3)
C11—C12—C13—C140.6 (4)O12—N1—C24—C25172.2 (3)
Cl1—C12—C13—C14178.3 (2)O11—N1—C24—C257.9 (4)
C12—C13—C14—C151.4 (4)C23—C24—C25—C260.6 (5)
C12—C13—C14—Cl2178.6 (2)N1—C24—C25—C26179.8 (3)
C13—C14—C15—C161.0 (4)C24—C25—C26—C210.5 (5)
Cl2—C14—C15—C16179.0 (2)C22—C21—C26—C250.4 (4)
C12—C11—C16—C150.9 (4)C3—C21—C26—C25178.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···Cl2i0.952.833.678 (3)149
C22—H22···O11ii0.952.583.455 (4)153
C23—H23···O12iii0.952.513.216 (4)131
C25—H25···O1iv0.952.463.255 (4)141
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x1, y1, z; (iii) x+1, y1/2, z+2; (iv) x+1, y+1, z.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds