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In the title compound, C17H13NO3, the dihedral angle between the benzene rings is 2.57 (4)°. The crystal structure is stabilized by C—H...O inter­actions, which form a three-dimensional network, and by C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807014663/sj2268sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807014663/sj2268Isup2.hkl
Contains datablock I

CCDC reference: 647336

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.042
  • wR factor = 0.115
  • Data-to-parameter ratio = 18.5

checkCIF/PLATON results

No syntax errors found



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 35.41 From the CIF: _reflns_number_total 3523 Count of symmetry unique reflns 3528 Completeness (_total/calc) 99.86% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 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 0 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: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

(2E,4E)-1-(3-nitrophenyl)-5-phenylpenta-2,4-dien-1-one top
Crystal data top
C17H13NO3F(000) = 584
Mr = 279.28Dx = 1.346 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 9853 reflections
a = 7.0167 (1) Åθ = 2.1–35.4°
b = 12.1953 (2) ŵ = 0.09 mm1
c = 16.1081 (3) ÅT = 100 K
V = 1378.38 (4) Å3Block, yellow
Z = 40.47 × 0.26 × 0.14 mm
Data collection top
Bruker SMART APEX2 CCD
diffractometer
3523 independent reflections
Radiation source: fine-focus sealed tube3097 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
Detector resolution: 8.33 pixels mm-1θmax = 35.4°, θmin = 2.1°
ω scansh = 1011
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1919
Tmin = 0.864, Tmax = 0.988l = 2626
38028 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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.061P)2 + 0.1877P]
where P = (Fo2 + 2Fc2)/3
3523 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.21 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
O10.34727 (18)0.73359 (9)0.12193 (7)0.0294 (2)
O20.94246 (17)0.62305 (9)0.23880 (7)0.0290 (2)
O31.09835 (18)0.72784 (10)0.32353 (8)0.0335 (3)
N10.95979 (18)0.70772 (10)0.27986 (7)0.0226 (2)
C10.4708 (2)1.09237 (11)0.05561 (9)0.0233 (3)
H1A0.38361.12380.09200.028*
C20.6389 (2)1.14710 (12)0.03679 (10)0.0271 (3)
H2A0.66301.21520.06050.033*
C30.7714 (2)1.10129 (13)0.01699 (9)0.0269 (3)
H3A0.88371.13840.02920.032*
C40.7352 (2)0.99967 (13)0.05238 (8)0.0248 (3)
H4A0.82400.96810.08800.030*
C50.5666 (2)0.94528 (11)0.03472 (8)0.0217 (2)
H5A0.54230.87790.05960.026*
C60.43218 (19)0.98992 (11)0.01995 (8)0.0190 (2)
C70.2572 (2)0.92819 (11)0.03565 (8)0.0197 (2)
H7A0.23630.86720.00220.024*
C80.12297 (19)0.94964 (11)0.09310 (8)0.0203 (2)
H8A0.13701.01020.12770.024*
C90.0413 (2)0.88066 (11)0.10181 (8)0.0202 (2)
H9A0.05400.82270.06470.024*
C100.1788 (2)0.89318 (11)0.15938 (8)0.0208 (2)
H10A0.17060.95070.19710.025*
C110.3408 (2)0.81782 (10)0.16367 (8)0.0193 (2)
C120.50404 (19)0.84422 (10)0.22038 (8)0.0175 (2)
C130.6496 (2)0.76658 (10)0.22655 (8)0.0184 (2)
H13A0.64140.70060.19790.022*
C140.80556 (19)0.78903 (10)0.27573 (8)0.0183 (2)
C150.8250 (2)0.88628 (11)0.31965 (8)0.0213 (2)
H15A0.93150.89920.35260.026*
C160.6810 (2)0.96359 (11)0.31295 (9)0.0231 (3)
H16A0.69081.02970.34140.028*
C170.5215 (2)0.94281 (11)0.26378 (8)0.0204 (2)
H17A0.42560.99520.25990.025*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0328 (6)0.0222 (4)0.0330 (5)0.0040 (4)0.0108 (5)0.0077 (4)
O20.0301 (6)0.0219 (4)0.0351 (5)0.0060 (4)0.0021 (5)0.0033 (4)
O30.0277 (6)0.0332 (6)0.0396 (6)0.0059 (5)0.0126 (5)0.0000 (5)
N10.0226 (5)0.0213 (5)0.0240 (5)0.0027 (4)0.0009 (4)0.0033 (4)
C10.0213 (6)0.0228 (5)0.0256 (6)0.0006 (5)0.0006 (5)0.0033 (5)
C20.0263 (7)0.0232 (6)0.0317 (7)0.0039 (5)0.0027 (6)0.0007 (5)
C30.0206 (6)0.0305 (7)0.0295 (6)0.0040 (5)0.0011 (5)0.0063 (5)
C40.0221 (6)0.0291 (6)0.0233 (5)0.0007 (5)0.0035 (5)0.0026 (5)
C50.0225 (6)0.0226 (5)0.0200 (5)0.0008 (5)0.0014 (5)0.0005 (4)
C60.0178 (5)0.0208 (5)0.0185 (5)0.0008 (4)0.0007 (4)0.0009 (4)
C70.0184 (5)0.0204 (5)0.0203 (5)0.0012 (5)0.0009 (4)0.0002 (4)
C80.0179 (5)0.0222 (5)0.0209 (5)0.0003 (5)0.0000 (4)0.0002 (4)
C90.0188 (5)0.0203 (5)0.0215 (5)0.0010 (5)0.0001 (4)0.0016 (4)
C100.0190 (5)0.0215 (5)0.0219 (5)0.0001 (5)0.0008 (4)0.0006 (4)
C110.0193 (5)0.0186 (5)0.0200 (5)0.0009 (4)0.0019 (4)0.0001 (4)
C120.0172 (5)0.0168 (5)0.0186 (5)0.0008 (4)0.0006 (4)0.0001 (4)
C130.0202 (6)0.0157 (5)0.0193 (5)0.0004 (4)0.0003 (4)0.0005 (4)
C140.0179 (5)0.0181 (5)0.0190 (5)0.0008 (4)0.0005 (4)0.0027 (4)
C150.0195 (5)0.0227 (5)0.0217 (5)0.0025 (5)0.0013 (4)0.0024 (5)
C160.0222 (6)0.0202 (5)0.0268 (6)0.0010 (5)0.0013 (5)0.0060 (5)
C170.0187 (5)0.0188 (5)0.0238 (5)0.0002 (5)0.0001 (4)0.0035 (4)
Geometric parameters (Å, º) top
O1—C111.2285 (15)C8—C91.4340 (19)
O2—N11.2322 (15)C8—H8A0.9300
O3—N11.2249 (16)C9—C101.3466 (18)
N1—C141.4693 (18)C9—H9A0.9300
C1—C21.389 (2)C10—C111.4636 (19)
C1—C61.4016 (19)C10—H10A0.9300
C1—H1A0.9300C11—C121.5001 (18)
C2—C31.388 (2)C12—C171.3962 (17)
C2—H2A0.9300C12—C131.3962 (18)
C3—C41.388 (2)C13—C141.3784 (18)
C3—H3A0.9300C13—H13A0.9300
C4—C51.385 (2)C14—C151.3877 (18)
C4—H4A0.9300C15—C161.386 (2)
C5—C61.4007 (19)C15—H15A0.9300
C5—H5A0.9300C16—C171.3943 (19)
C6—C71.4622 (19)C16—H16A0.9300
C7—C81.3462 (19)C17—H17A0.9300
C7—H7A0.9300
O3—N1—O2123.67 (13)C10—C9—C8125.21 (12)
O3—N1—C14118.39 (11)C10—C9—H9A117.4
O2—N1—C14117.94 (12)C8—C9—H9A117.4
C2—C1—C6120.20 (13)C9—C10—C11121.17 (12)
C2—C1—H1A119.9C9—C10—H10A119.4
C6—C1—H1A119.9C11—C10—H10A119.4
C3—C2—C1120.77 (13)O1—C11—C10121.87 (12)
C3—C2—H2A119.6O1—C11—C12118.98 (12)
C1—C2—H2A119.6C10—C11—C12119.15 (11)
C4—C3—C2119.55 (14)C17—C12—C13118.95 (11)
C4—C3—H3A120.2C17—C12—C11123.83 (11)
C2—C3—H3A120.2C13—C12—C11117.16 (11)
C5—C4—C3119.97 (14)C14—C13—C12119.14 (11)
C5—C4—H4A120.0C14—C13—H13A120.4
C3—C4—H4A120.0C12—C13—H13A120.4
C4—C5—C6121.20 (13)C13—C14—C15122.73 (12)
C4—C5—H5A119.4C13—C14—N1118.47 (11)
C6—C5—H5A119.4C15—C14—N1118.77 (12)
C5—C6—C1118.29 (13)C16—C15—C14118.03 (12)
C5—C6—C7118.30 (12)C16—C15—H15A121.0
C1—C6—C7123.40 (12)C14—C15—H15A121.0
C8—C7—C6127.32 (12)C15—C16—C17120.38 (12)
C8—C7—H7A116.3C15—C16—H16A119.8
C6—C7—H7A116.3C17—C16—H16A119.8
C7—C8—C9121.05 (12)C16—C17—C12120.75 (12)
C7—C8—H8A119.5C16—C17—H17A119.6
C9—C8—H8A119.5C12—C17—H17A119.6
C6—C1—C2—C30.4 (2)O1—C11—C12—C134.30 (18)
C1—C2—C3—C40.1 (2)C10—C11—C12—C13175.93 (11)
C2—C3—C4—C50.8 (2)C17—C12—C13—C140.48 (18)
C3—C4—C5—C61.3 (2)C11—C12—C13—C14177.81 (11)
C4—C5—C6—C11.0 (2)C12—C13—C14—C150.16 (19)
C4—C5—C6—C7179.88 (12)C12—C13—C14—N1178.43 (11)
C2—C1—C6—C50.2 (2)O3—N1—C14—C13179.94 (12)
C2—C1—C6—C7178.98 (13)O2—N1—C14—C130.17 (18)
C5—C6—C7—C8171.02 (13)O3—N1—C14—C151.60 (19)
C1—C6—C7—C810.2 (2)O2—N1—C14—C15178.17 (12)
C6—C7—C8—C9179.39 (12)C13—C14—C15—C160.3 (2)
C7—C8—C9—C10177.30 (13)N1—C14—C15—C16177.95 (12)
C8—C9—C10—C11179.56 (12)C14—C15—C16—C170.5 (2)
C9—C10—C11—O18.6 (2)C15—C16—C17—C120.2 (2)
C9—C10—C11—C12171.19 (12)C13—C12—C17—C160.33 (19)
O1—C11—C12—C17172.88 (13)C11—C12—C17—C16177.47 (13)
C10—C11—C12—C176.89 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7A···O1i0.932.423.297 (2)157
C10—H10A···O2ii0.932.473.358 (2)159
C16—H16A···O1ii0.932.573.462 (2)161
C15—H15A···Cg1iii0.932.763.612 (1)152
Symmetry codes: (i) x1/2, y+3/2, z; (ii) x+1, y+1/2, z+1/2; (iii) x+1/2, y+2, z+1/2.
 

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