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The crystal structure of 4-nitro­phenyl­propiolic acid, C9H5NO4, is described. The carboxyl­ic acid functional group adopts the rare syn-anti conformation and the mol­ecules are arranged in a catemeric chain.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805013310/gh6020sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805013310/gh6020Isup2.hkl
Contains datablock I

CCDC reference: 274399

Key indicators

  • Single-crystal X-ray study
  • T = 223 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.058
  • wR factor = 0.163
  • Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.27 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C1 - C2 ... 1.44 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C3 - C4 ... 1.43 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H9 .. O2 .. 2.70 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000) and X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXTL.

4-nitrophenylpropynoic acid top
Crystal data top
C9H5NO4F(000) = 392
Mr = 191.14Dx = 1.514 Mg m3
Monoclinic, P21/nMelting point: 474(2) K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 3.726 (2) ÅCell parameters from 2334 reflections
b = 7.511 (5) Åθ = 3.0–26.9°
c = 29.983 (18) ŵ = 0.12 mm1
β = 91.937 (12)°T = 223 K
V = 838.6 (9) Å3Rod, yellow
Z = 40.32 × 0.21 × 0.12 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
2065 independent reflections
Radiation source: fine-focus sealed tube1200 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.055
φ and ω scansθmax = 28.4°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Blessing, 1995)
h = 44
Tmin = 0.962, Tmax = 0.986k = 109
5168 measured reflectionsl = 2140
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)] = 0.058Hydrogen site location: difference Fourier map
wR(F2) = 0.163H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0814P)2]
where P = (Fo2 + 2Fc2)/3
2065 reflections(Δ/σ)max < 0.001
134 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.31 e Å3
Special details top

Experimental. Crystals were grown by slow evaporation from a mixture of acetonitrile and carbon tetrachloride

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*/UeqOcc. (<1)
O10.5047 (5)0.1751 (2)0.00247 (5)0.0446 (5)
O20.3341 (5)0.4175 (2)0.03411 (6)0.0546 (6)
H20.44 (2)0.448 (8)0.007 (2)0.082*0.50
O30.6415 (6)0.4808 (3)0.23541 (6)0.0739 (7)
O40.5499 (8)0.6644 (3)0.18114 (9)0.0998 (9)
N10.5272 (6)0.5168 (3)0.19849 (8)0.0517 (6)
C10.3514 (6)0.2494 (3)0.03076 (7)0.0369 (5)
C20.1875 (6)0.1423 (3)0.06561 (7)0.0371 (6)
C30.0659 (6)0.0336 (3)0.09100 (7)0.0354 (5)
C40.0778 (6)0.1043 (3)0.11950 (7)0.0309 (5)
C50.2032 (6)0.0697 (3)0.16287 (7)0.0383 (6)
H50.19030.04640.17440.046*
C60.3459 (6)0.2046 (3)0.18887 (7)0.0385 (6)
H60.43190.18250.21820.046*
C70.3599 (6)0.3739 (3)0.17082 (7)0.0343 (5)
C80.2321 (6)0.4123 (3)0.12852 (8)0.0406 (6)
H80.24150.52920.11750.049*
C90.0900 (6)0.2776 (3)0.10251 (7)0.0372 (6)
H90.00130.30160.07340.045*
H10.475 (16)0.077 (7)0.0023 (19)0.055 (19)*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0652 (12)0.0218 (9)0.0459 (9)0.0034 (8)0.0117 (8)0.0048 (7)
O20.0782 (14)0.0204 (9)0.0634 (12)0.0010 (8)0.0221 (10)0.0036 (7)
O30.0859 (17)0.0737 (14)0.0604 (12)0.0076 (12)0.0239 (11)0.0282 (11)
O40.138 (2)0.0320 (12)0.1263 (19)0.0161 (13)0.0419 (17)0.0135 (12)
N10.0470 (14)0.0419 (13)0.0657 (14)0.0017 (10)0.0056 (11)0.0232 (11)
C10.0387 (14)0.0249 (11)0.0471 (13)0.0050 (10)0.0005 (11)0.0077 (9)
C20.0401 (14)0.0242 (11)0.0464 (13)0.0014 (9)0.0045 (10)0.0037 (9)
C30.0303 (12)0.0308 (11)0.0452 (12)0.0033 (10)0.0005 (10)0.0047 (10)
C40.0272 (12)0.0277 (10)0.0377 (11)0.0024 (9)0.0001 (9)0.0067 (9)
C50.0418 (14)0.0277 (11)0.0453 (13)0.0022 (9)0.0001 (11)0.0009 (9)
C60.0391 (13)0.0383 (13)0.0376 (11)0.0056 (10)0.0070 (10)0.0021 (9)
C70.0285 (12)0.0282 (11)0.0459 (12)0.0025 (9)0.0016 (10)0.0122 (9)
C80.0468 (15)0.0244 (11)0.0504 (13)0.0017 (10)0.0002 (11)0.0012 (9)
C90.0416 (14)0.0330 (12)0.0365 (11)0.0031 (10)0.0046 (10)0.0002 (9)
Geometric parameters (Å, º) top
O1—C11.262 (3)C4—C51.391 (3)
O1—H10.75 (5)C4—C91.399 (3)
O2—C11.268 (3)C5—C61.375 (3)
O2—H20.92 (6)C5—H50.9400
O3—N11.203 (3)C6—C71.383 (3)
O4—N11.229 (3)C6—H60.9400
N1—C71.481 (3)C7—C81.370 (3)
C1—C21.438 (3)C8—C91.373 (3)
C2—C31.195 (3)C8—H80.9400
C3—C41.435 (3)C9—H90.9400
C1—O1—H1112 (5)C6—C5—H5119.9
C1—O2—H299 (4)C4—C5—H5119.9
O3—N1—O4124.4 (2)C5—C6—C7118.3 (2)
O3—N1—C7118.8 (2)C5—C6—H6120.8
O4—N1—C7116.8 (2)C7—C6—H6120.8
O1—C1—O2121.5 (2)C8—C7—C6122.6 (2)
O1—C1—C2119.8 (2)C8—C7—N1119.5 (2)
O2—C1—C2118.7 (2)C6—C7—N1117.9 (2)
C3—C2—C1170.9 (2)C7—C8—C9119.1 (2)
C2—C3—C4176.7 (2)C7—C8—H8120.5
C5—C4—C9120.0 (2)C9—C8—H8120.5
C5—C4—C3121.9 (2)C8—C9—C4119.7 (2)
C9—C4—C3118.1 (2)C8—C9—H9120.2
C6—C5—C4120.2 (2)C4—C9—H9120.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O1i0.75 (5)1.90 (5)2.635 (3)168 (6)
O2—H2···O2ii0.92 (6)1.78 (6)2.660 (3)158 (6)
C5—H5···O4iii0.942.563.345 (4)142
C6—H6···O3iv0.942.573.367 (4)143
C9—H9···O2v0.942.703.425 (3)134
Symmetry codes: (i) x1, y, z; (ii) x1, y1, z; (iii) x, y1, z; (iv) x+3/2, y1/2, z+1/2; (v) x, y+1, z.
 

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