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The crystal structure of a non-centrosymmetric polymorphic modification of the title compound, C9H7NO4, determined at 130 K, shows the presence of 21 screw-generated one-dimensional zigzag chains formed through catemeric C(4) synanti carboxylic acid hydrogen-bonding associations.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806014048/fl2018sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806014048/fl2018Isup2.hkl
Contains datablock I

CCDC reference: 608331

Key indicators

  • Single-crystal X-ray study
  • T = 130 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.063
  • wR factor = 0.111
  • Data-to-parameter ratio = 6.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.38 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C7 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.34 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
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 25.00 From the CIF: _reflns_number_total 810 Count of symmetry unique reflns 810 Completeness (_total/calc) 100.00% 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 4 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 2 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997) in WinGX (Farrugia, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) in WinGX (Farrugia, 1999); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

trans-3-(2-nitrophenyl)prop-2-enoic acid top
Crystal data top
C9H7NO4F(000) = 200
Mr = 193.16Dx = 1.537 Mg m3
Monoclinic, P21Melting point: 513 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 3.6850 (18) ÅCell parameters from 219 reflections
b = 7.074 (4) Åθ = 2.5–16.7°
c = 16.073 (8) ŵ = 0.12 mm1
β = 94.978 (11)°T = 130 K
V = 417.4 (4) Å3Plate, yellow
Z = 20.30 × 0.20 × 0.03 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
578 reflections with I > 2σ(I
Radiation source: sealed tubeRint = 0.096
Graphite monochromatorθmax = 25.0°, θmin = 1.3°
φ and ω scansh = 42
2152 measured reflectionsk = 88
810 independent reflectionsl = 1917
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)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 0.81 w = 1/[σ2(Fo2) + (0.0161P)2]
where P = (Fo2 + 2Fc2)/3
810 reflections(Δ/σ)max < 0.001
127 parametersΔρmax = 0.21 e Å3
1 restraintΔρmin = 0.23 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O211.0466 (11)0.3100 (5)0.8391 (2)0.0398 (16)
O220.7878 (12)0.3815 (5)0.9506 (3)0.0537 (19)
O910.8097 (14)0.1389 (6)0.5897 (3)0.0576 (18)
O920.9943 (14)0.3380 (6)0.4917 (3)0.0563 (19)
N20.8583 (13)0.4136 (6)0.8786 (3)0.0351 (19)
C10.6333 (18)0.5951 (9)0.7522 (4)0.043 (3)
C20.6942 (16)0.5846 (8)0.8373 (4)0.032 (2)
C30.6254 (18)0.7309 (8)0.8899 (4)0.038 (3)
C40.4812 (18)0.8990 (9)0.8554 (5)0.051 (3)
C50.4196 (17)0.9123 (9)0.7716 (4)0.047 (3)
C60.4842 (17)0.7682 (7)0.7196 (4)0.042 (3)
C70.697 (2)0.4400 (9)0.6943 (4)0.072 (3)
C80.803 (3)0.4654 (9)0.6161 (5)0.074 (4)
C90.8736 (19)0.3128 (10)0.5586 (4)0.052 (3)
H30.674900.718100.948700.0460*
H40.427601.001900.890300.0620*
H50.327001.027700.748200.0570*
H60.429800.782500.661100.0500*
H70.662100.314200.712600.0870*
H80.833700.591500.597700.0890*
H910.877000.036000.562000.0690*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O210.039 (3)0.027 (2)0.055 (3)0.009 (2)0.014 (2)0.007 (2)
O220.079 (4)0.047 (3)0.038 (3)0.008 (2)0.022 (3)0.009 (2)
O910.087 (4)0.025 (2)0.062 (3)0.004 (3)0.014 (3)0.001 (3)
O920.091 (4)0.024 (3)0.052 (3)0.001 (3)0.004 (3)0.003 (2)
N20.026 (3)0.035 (3)0.045 (4)0.003 (3)0.008 (3)0.002 (3)
C10.064 (5)0.027 (4)0.035 (4)0.003 (4)0.007 (4)0.003 (3)
C20.030 (4)0.025 (3)0.040 (4)0.002 (3)0.003 (3)0.004 (3)
C30.042 (5)0.038 (4)0.037 (5)0.004 (3)0.014 (3)0.002 (4)
C40.049 (5)0.032 (4)0.076 (6)0.003 (4)0.021 (4)0.001 (4)
C50.049 (5)0.033 (4)0.061 (5)0.002 (4)0.012 (4)0.018 (4)
C60.054 (5)0.029 (4)0.041 (5)0.014 (3)0.008 (4)0.012 (4)
C70.140 (8)0.029 (4)0.058 (5)0.016 (4)0.017 (5)0.007 (4)
C80.147 (9)0.025 (4)0.052 (6)0.006 (4)0.018 (5)0.004 (4)
C90.070 (6)0.028 (4)0.055 (5)0.006 (4)0.007 (4)0.012 (4)
Geometric parameters (Å, º) top
O21—N21.224 (6)C4—C51.350 (10)
O22—N21.229 (7)C5—C61.352 (9)
O91—C91.356 (8)C7—C81.360 (11)
O92—C91.212 (8)C8—C91.459 (10)
O91—H910.900C3—H30.9500
N2—C21.483 (7)C4—H40.9500
C1—C21.369 (9)C5—H50.9500
C1—C61.423 (8)C6—H60.9500
C1—C71.471 (9)C7—H70.9500
C2—C31.374 (9)C8—H80.9500
C3—C41.397 (9)
C9—O91—H91119.0O91—C9—C8113.0 (6)
O21—N2—C2118.9 (5)O92—C9—C8123.5 (7)
O22—N2—C2117.4 (5)O91—C9—O92123.3 (6)
O21—N2—O22123.6 (4)C2—C3—H3121.00
C2—C1—C7124.8 (6)C4—C3—H3121.00
C6—C1—C7119.1 (6)C3—C4—H4121.00
C2—C1—C6116.1 (6)C5—C4—H4121.00
N2—C2—C1121.1 (5)C4—C5—H5119.00
N2—C2—C3115.4 (5)C6—C5—H5119.00
C1—C2—C3123.4 (6)C1—C6—H6120.00
C2—C3—C4118.8 (6)C5—C6—H6120.00
C3—C4—C5118.7 (6)C1—C7—H7118.00
C4—C5—C6122.7 (6)C8—C7—H7118.00
C1—C6—C5120.3 (6)C7—C8—H8118.00
C1—C7—C8124.1 (6)C9—C8—H8118.00
C7—C8—C9124.7 (6)
O21—N2—C2—C3153.3 (5)C6—C1—C2—C31.2 (9)
O21—N2—C2—C124.0 (8)C7—C1—C2—N24.3 (10)
O22—N2—C2—C1154.0 (6)N2—C2—C3—C4178.1 (5)
O22—N2—C2—C328.7 (7)C1—C2—C3—C40.9 (10)
C6—C1—C2—N2178.3 (5)C2—C3—C4—C50.9 (10)
C7—C1—C2—C3178.7 (6)C3—C4—C5—C61.5 (10)
C2—C1—C6—C51.7 (9)C4—C5—C6—C11.9 (10)
C7—C1—C6—C5179.3 (6)C1—C7—C8—C9178.8 (8)
C2—C1—C7—C8147.8 (8)C7—C8—C9—O92174.2 (8)
C6—C1—C7—C834.8 (11)C7—C8—C9—O912.3 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O91—H91···O92i0.901.732.632 (7)180
C7—H7···O210.952.382.721 (8)101
C7—H7···O910.952.432.767 (8)100
C8—H8···O92ii0.952.383.276 (9)157
Symmetry codes: (i) x+2, y1/2, z+1; (ii) x+2, y+1/2, z+1.
 

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