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The title mol­ecule, C16H13NO4, crystallizes with two mol­ecules in the asymmetric unit. The dihedral angles between the two benzene rings are 5.1 (2) and 6.2 (2)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807001432/hb2266sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807001432/hb2266Isup2.hkl
Contains datablock I

CCDC reference: 636664

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.088
  • wR factor = 0.205
  • Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 34 Perc.
Alert level C CELLV02_ALERT_1_C The supplied cell volume s.u. differs from that calculated from the cell parameter s.u.'s by > 2 Calculated cell volume su = 11.15 Cell volume su given = 9.00 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) . 300 Ang. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 6 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 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

(E)-3-(4-Methoxyphenyl)-1-(3-nitrophenyl)prop-2-en-1-one top
Crystal data top
C16H13NO4F(000) = 1184
Mr = 283.27Dx = 1.407 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 920 reflections
a = 13.252 (3) Åθ = 2.3–25.5°
b = 15.431 (3) ŵ = 0.10 mm1
c = 13.974 (3) ÅT = 293 K
β = 110.62 (3)°Block, yellow
V = 2674.5 (9) Å30.20 × 0.20 × 0.10 mm
Z = 8
Data collection top
Bruker SMART CCD
diffractometer
5229 independent reflections
Radiation source: fine-focus sealed tube1760 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.013
ω scansθmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 016
Tmin = 0.980, Tmax = 0.990k = 019
5459 measured reflectionsl = 1716
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)] = 0.088Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.205H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0598P)2]
where P = (Fo2 + 2Fc2)/3
5229 reflections(Δ/σ)max < 0.001
381 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.35 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
C10.2380 (5)0.6687 (4)0.8676 (4)0.0426 (15)
C20.1471 (5)0.6454 (4)0.8869 (4)0.0559 (18)
H20.12940.58750.89090.067*
C30.0829 (5)0.7114 (4)0.9002 (5)0.0600 (18)
H30.02020.69770.91250.072*
C40.1101 (4)0.7974 (4)0.8957 (4)0.0494 (16)
H40.06650.84090.90610.059*
C50.2031 (4)0.8191 (3)0.8754 (4)0.0381 (15)
C60.2673 (4)0.7531 (3)0.8622 (4)0.0435 (15)
H60.33010.76590.84970.052*
C70.2379 (5)0.9113 (4)0.8701 (4)0.0451 (16)
C80.1657 (4)0.9820 (3)0.8718 (4)0.0448 (16)
H80.10100.96980.88110.054*
C90.1914 (4)1.0642 (4)0.8602 (4)0.0447 (15)
H90.25631.07270.85000.054*
C100.1297 (4)1.1419 (4)0.8616 (4)0.0433 (16)
C110.0288 (5)1.1390 (4)0.8720 (4)0.0477 (16)
H110.00231.08580.87640.057*
C120.0251 (4)1.2147 (4)0.8757 (4)0.0474 (16)
H120.09261.21210.88200.057*
C130.0203 (5)1.2943 (4)0.8702 (4)0.0479 (17)
C140.1195 (5)1.2984 (3)0.8583 (4)0.0460 (16)
H140.15041.35160.85340.055*
C150.1715 (5)1.2224 (3)0.8538 (4)0.0464 (15)
H150.23781.22530.84510.056*
C160.0081 (5)1.4486 (3)0.8774 (4)0.0599 (18)
H16A0.07421.45130.93520.090*
H16B0.04051.49240.88390.090*
H16C0.02301.45810.81580.090*
C170.7407 (4)0.8879 (4)0.8730 (4)0.0426 (15)
C180.6427 (4)0.9111 (4)0.8789 (4)0.0532 (17)
H180.62380.96910.87950.064*
C190.5736 (5)0.8463 (4)0.8838 (5)0.0645 (19)
H190.50650.86010.88680.077*
C200.6043 (5)0.7600 (4)0.8845 (4)0.0520 (17)
H200.55720.71640.88780.062*
C210.7039 (4)0.7382 (4)0.8802 (4)0.0398 (15)
C220.7728 (4)0.8040 (3)0.8739 (4)0.0431 (16)
H220.83980.79090.87030.052*
C230.7407 (5)0.6469 (4)0.8810 (4)0.0454 (16)
C240.6720 (5)0.5751 (4)0.8868 (4)0.0513 (17)
H240.60960.58760.90020.062*
C250.6931 (4)0.4932 (4)0.8741 (4)0.0476 (16)
H250.75670.48370.86160.057*
C260.6321 (5)0.4160 (4)0.8766 (4)0.0453 (16)
C270.5308 (5)0.4179 (4)0.8891 (4)0.0522 (16)
H270.50050.47100.89540.063*
C280.4764 (5)0.3433 (4)0.8920 (4)0.0553 (18)
H280.41080.34600.90220.066*
C290.5187 (5)0.2632 (4)0.8799 (4)0.0484 (17)
C300.6162 (5)0.2590 (4)0.8667 (4)0.0493 (17)
H300.64510.20570.85890.059*
C310.6706 (5)0.3341 (4)0.8652 (4)0.0482 (16)
H310.73660.33030.85600.058*
C320.4996 (5)0.1105 (4)0.8790 (5)0.067 (2)
H32A0.51610.10490.81770.100*
H32B0.44800.06700.87960.100*
H32C0.56420.10310.93750.100*
N10.3068 (4)0.5978 (3)0.8527 (4)0.0544 (14)
N20.8148 (5)0.9579 (3)0.8701 (4)0.0595 (15)
O10.3869 (3)0.6181 (3)0.8329 (3)0.0710 (13)
O20.2810 (4)0.5234 (3)0.8614 (3)0.0753 (14)
O30.3263 (3)0.9234 (2)0.8638 (3)0.0661 (13)
O40.0401 (3)1.3648 (2)0.8735 (3)0.0567 (12)
O50.8996 (4)0.9374 (3)0.8595 (4)0.0894 (17)
O60.7891 (4)1.0329 (2)0.8778 (3)0.0757 (14)
O70.8301 (3)0.6321 (2)0.8769 (3)0.0631 (13)
O80.4557 (3)0.1940 (3)0.8821 (3)0.0655 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.048 (4)0.032 (4)0.045 (4)0.012 (3)0.014 (3)0.003 (3)
C20.058 (4)0.040 (4)0.074 (5)0.005 (3)0.029 (4)0.009 (3)
C30.051 (4)0.053 (4)0.085 (5)0.001 (4)0.034 (4)0.009 (4)
C40.042 (4)0.048 (4)0.063 (4)0.012 (3)0.024 (3)0.005 (3)
C50.032 (3)0.038 (3)0.041 (4)0.001 (3)0.008 (3)0.002 (3)
C60.043 (4)0.037 (4)0.049 (4)0.005 (3)0.015 (3)0.001 (3)
C70.036 (4)0.050 (4)0.048 (4)0.004 (3)0.013 (3)0.001 (3)
C80.037 (4)0.034 (3)0.063 (4)0.002 (3)0.017 (3)0.003 (3)
C90.040 (4)0.051 (4)0.045 (4)0.001 (3)0.016 (3)0.002 (3)
C100.034 (4)0.046 (4)0.048 (4)0.001 (3)0.012 (3)0.003 (3)
C110.044 (4)0.033 (3)0.064 (4)0.003 (3)0.017 (3)0.001 (3)
C120.039 (4)0.048 (4)0.060 (4)0.007 (3)0.024 (3)0.004 (3)
C130.045 (4)0.040 (4)0.059 (4)0.005 (3)0.018 (3)0.002 (3)
C140.056 (4)0.029 (3)0.055 (4)0.000 (3)0.023 (3)0.001 (3)
C150.042 (4)0.044 (4)0.054 (4)0.006 (3)0.018 (3)0.000 (3)
C160.070 (5)0.035 (4)0.073 (5)0.005 (3)0.022 (4)0.007 (3)
C170.035 (3)0.038 (4)0.051 (4)0.000 (3)0.010 (3)0.002 (3)
C180.047 (4)0.042 (4)0.070 (5)0.010 (3)0.020 (4)0.001 (3)
C190.046 (4)0.057 (4)0.098 (5)0.001 (4)0.034 (4)0.011 (4)
C200.048 (4)0.050 (4)0.062 (4)0.002 (3)0.024 (3)0.003 (3)
C210.041 (4)0.041 (4)0.038 (4)0.009 (3)0.015 (3)0.007 (3)
C220.039 (4)0.042 (4)0.053 (4)0.002 (3)0.022 (3)0.000 (3)
C230.060 (4)0.033 (4)0.044 (4)0.001 (3)0.019 (3)0.006 (3)
C240.048 (4)0.052 (4)0.057 (4)0.008 (3)0.023 (3)0.003 (3)
C250.040 (4)0.047 (4)0.059 (4)0.008 (3)0.020 (3)0.003 (3)
C260.050 (4)0.034 (4)0.052 (4)0.002 (3)0.017 (3)0.002 (3)
C270.052 (4)0.043 (4)0.062 (4)0.010 (3)0.022 (3)0.002 (3)
C280.054 (4)0.047 (4)0.074 (5)0.007 (3)0.034 (4)0.000 (3)
C290.054 (4)0.031 (4)0.059 (4)0.004 (3)0.019 (4)0.002 (3)
C300.041 (4)0.046 (4)0.059 (4)0.006 (3)0.015 (3)0.010 (3)
C310.041 (4)0.050 (4)0.057 (4)0.001 (3)0.020 (3)0.005 (3)
C320.064 (5)0.047 (4)0.084 (5)0.006 (4)0.020 (4)0.002 (4)
N10.062 (4)0.043 (3)0.063 (4)0.002 (3)0.028 (3)0.002 (3)
N20.062 (4)0.047 (4)0.074 (4)0.004 (3)0.031 (3)0.006 (3)
O10.070 (3)0.047 (3)0.112 (4)0.008 (2)0.051 (3)0.000 (2)
O20.089 (4)0.039 (3)0.109 (4)0.003 (3)0.049 (3)0.003 (3)
O30.053 (3)0.040 (3)0.113 (4)0.001 (2)0.039 (3)0.005 (2)
O40.056 (3)0.037 (2)0.080 (3)0.003 (2)0.028 (2)0.002 (2)
O50.062 (3)0.061 (3)0.162 (5)0.006 (2)0.060 (3)0.006 (3)
O60.090 (4)0.033 (3)0.112 (4)0.001 (3)0.046 (3)0.000 (3)
O70.053 (3)0.047 (3)0.101 (3)0.004 (2)0.041 (3)0.003 (2)
O80.060 (3)0.041 (3)0.104 (4)0.003 (2)0.039 (3)0.007 (2)
Geometric parameters (Å, º) top
C1—C61.368 (7)C17—N21.469 (7)
C1—C21.372 (7)C18—C191.374 (7)
C1—N11.486 (7)C18—H180.9300
C2—C31.381 (7)C19—C201.392 (7)
C2—H20.9300C19—H190.9300
C3—C41.383 (7)C20—C211.383 (7)
C3—H30.9300C20—H200.9300
C4—C51.399 (7)C21—C221.389 (7)
C4—H40.9300C21—C231.490 (7)
C5—C61.381 (7)C22—H220.9300
C5—C71.506 (7)C23—O71.227 (6)
C6—H60.9300C23—C241.455 (7)
C7—O31.219 (6)C24—C251.319 (7)
C7—C81.457 (7)C24—H240.9300
C8—C91.339 (7)C25—C261.448 (7)
C8—H80.9300C25—H250.9300
C9—C101.455 (7)C26—C311.392 (7)
C9—H90.9300C26—C271.414 (7)
C10—C151.381 (7)C27—C281.366 (7)
C10—C111.395 (7)C27—H270.9300
C11—C121.381 (7)C28—C291.392 (7)
C11—H110.9300C28—H280.9300
C12—C131.382 (7)C29—O81.363 (6)
C12—H120.9300C29—C301.368 (7)
C13—O41.360 (6)C30—C311.370 (7)
C13—C141.384 (7)C30—H300.9300
C14—C151.372 (7)C31—H310.9300
C14—H140.9300C32—O81.421 (6)
C15—H150.9300C32—H32A0.9600
C16—O41.435 (6)C32—H32B0.9600
C16—H16A0.9600C32—H32C0.9600
C16—H16B0.9600N1—O21.216 (5)
C16—H16C0.9600N1—O11.228 (5)
C17—C221.362 (7)N2—O61.222 (6)
C17—C181.377 (7)N2—O51.225 (6)
C6—C1—C2123.2 (6)C19—C18—H18120.9
C6—C1—N1119.5 (6)C17—C18—H18120.9
C2—C1—N1117.3 (5)C18—C19—C20119.9 (6)
C1—C2—C3117.2 (6)C18—C19—H19120.1
C1—C2—H2121.4C20—C19—H19120.1
C3—C2—H2121.4C21—C20—C19120.9 (6)
C2—C3—C4121.3 (6)C21—C20—H20119.5
C2—C3—H3119.4C19—C20—H20119.5
C4—C3—H3119.4C20—C21—C22118.9 (6)
C3—C4—C5120.1 (6)C20—C21—C23123.1 (6)
C3—C4—H4119.9C22—C21—C23118.1 (6)
C5—C4—H4119.9C17—C22—C21119.1 (6)
C6—C5—C4118.6 (5)C17—C22—H22120.5
C6—C5—C7118.5 (5)C21—C22—H22120.5
C4—C5—C7122.9 (5)O7—C23—C24119.6 (5)
C1—C6—C5119.6 (6)O7—C23—C21119.7 (6)
C1—C6—H6120.2C24—C23—C21120.7 (6)
C5—C6—H6120.2C25—C24—C23123.7 (6)
O3—C7—C8122.8 (6)C25—C24—H24118.1
O3—C7—C5117.8 (6)C23—C24—H24118.1
C8—C7—C5119.4 (5)C24—C25—C26129.7 (6)
C9—C8—C7120.7 (6)C24—C25—H25115.2
C9—C8—H8119.7C26—C25—H25115.2
C7—C8—H8119.7C31—C26—C27115.9 (6)
C8—C9—C10127.6 (6)C31—C26—C25120.9 (6)
C8—C9—H9116.2C27—C26—C25123.2 (6)
C10—C9—H9116.2C28—C27—C26121.2 (6)
C15—C10—C11117.6 (6)C28—C27—H27119.4
C15—C10—C9119.8 (5)C26—C27—H27119.4
C11—C10—C9122.6 (5)C27—C28—C29120.4 (6)
C12—C11—C10120.3 (6)C27—C28—H28119.8
C12—C11—H11119.9C29—C28—H28119.8
C10—C11—H11119.9O8—C29—C30125.5 (6)
C11—C12—C13120.6 (6)O8—C29—C28114.6 (6)
C11—C12—H12119.7C30—C29—C28119.9 (6)
C13—C12—H12119.7C29—C30—C31119.3 (6)
O4—C13—C12115.8 (6)C29—C30—H30120.4
O4—C13—C14124.3 (6)C31—C30—H30120.4
C12—C13—C14119.9 (6)C30—C31—C26123.4 (6)
C15—C14—C13118.7 (6)C30—C31—H31118.3
C15—C14—H14120.7C26—C31—H31118.3
C13—C14—H14120.7O8—C32—H32A109.5
C14—C15—C10122.9 (6)O8—C32—H32B109.5
C14—C15—H15118.5H32A—C32—H32B109.5
C10—C15—H15118.5O8—C32—H32C109.5
O4—C16—H16A109.5H32A—C32—H32C109.5
O4—C16—H16B109.5H32B—C32—H32C109.5
H16A—C16—H16B109.5O2—N1—O1124.0 (5)
O4—C16—H16C109.5O2—N1—C1118.2 (5)
H16A—C16—H16C109.5O1—N1—C1117.8 (5)
H16B—C16—H16C109.5O6—N2—O5123.4 (6)
C22—C17—C18123.0 (6)O6—N2—C17119.0 (6)
C22—C17—N2119.3 (5)O5—N2—C17117.7 (5)
C18—C17—N2117.6 (6)C13—O4—C16117.5 (5)
C19—C18—C17118.2 (6)C29—O8—C32116.7 (5)
C6—C1—C2—C30.7 (9)C18—C17—C22—C210.5 (9)
N1—C1—C2—C3179.7 (5)N2—C17—C22—C21177.8 (5)
C1—C2—C3—C40.9 (10)C20—C21—C22—C170.6 (8)
C2—C3—C4—C51.2 (9)C23—C21—C22—C17179.9 (5)
C3—C4—C5—C61.3 (8)C20—C21—C23—O7179.9 (6)
C3—C4—C5—C7179.5 (5)C22—C21—C23—O70.6 (8)
C2—C1—C6—C50.8 (9)C20—C21—C23—C240.3 (9)
N1—C1—C6—C5179.6 (5)C22—C21—C23—C24179.6 (5)
C4—C5—C6—C11.0 (8)O7—C23—C24—C259.6 (9)
C7—C5—C6—C1179.4 (5)C21—C23—C24—C25170.6 (6)
C6—C5—C7—O36.6 (8)C23—C24—C25—C26179.3 (6)
C4—C5—C7—O3171.7 (5)C24—C25—C26—C31177.5 (6)
C6—C5—C7—C8172.9 (5)C24—C25—C26—C273.5 (10)
C4—C5—C7—C88.8 (8)C31—C26—C27—C281.5 (9)
O3—C7—C8—C94.1 (9)C25—C26—C27—C28179.4 (6)
C5—C7—C8—C9175.4 (5)C26—C27—C28—C291.8 (9)
C7—C8—C9—C10178.9 (5)C27—C28—C29—O8178.6 (6)
C8—C9—C10—C15176.5 (6)C27—C28—C29—C301.1 (9)
C8—C9—C10—C112.7 (9)O8—C29—C30—C31179.4 (6)
C15—C10—C11—C121.0 (9)C28—C29—C30—C310.3 (9)
C9—C10—C11—C12178.2 (5)C29—C30—C31—C260.2 (9)
C10—C11—C12—C130.6 (9)C27—C26—C31—C300.7 (9)
C11—C12—C13—O4179.4 (5)C25—C26—C31—C30179.9 (6)
C11—C12—C13—C141.6 (9)C6—C1—N1—O2177.4 (5)
O4—C13—C14—C15178.6 (5)C2—C1—N1—O22.2 (8)
C12—C13—C14—C151.0 (9)C6—C1—N1—O12.1 (8)
C13—C14—C15—C100.6 (9)C2—C1—N1—O1178.3 (6)
C11—C10—C15—C141.6 (9)C22—C17—N2—O6174.0 (6)
C9—C10—C15—C14177.6 (5)C18—C17—N2—O63.4 (8)
C22—C17—C18—C191.3 (9)C22—C17—N2—O56.3 (8)
N2—C17—C18—C19178.6 (5)C18—C17—N2—O5176.2 (6)
C17—C18—C19—C201.0 (9)C12—C13—O4—C16174.5 (5)
C18—C19—C20—C210.1 (10)C14—C13—O4—C167.9 (8)
C19—C20—C21—C220.9 (9)C30—C29—O8—C325.5 (9)
C19—C20—C21—C23179.8 (6)C28—C29—O8—C32174.7 (5)
 

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