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, C7H4ClNO4, the mol­ecules form centrosymmetric dimers through O—H...O hydrogen bonds. The dimers are connected by C—H...O hydrogen bonds to form molecular tapes. Disorder of the H atom in the O—H...O hydrogen bond is suggested.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803026394/lh6142sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803026394/lh6142Isup2.hkl
Contains datablock I

CCDC reference: 227903

Key indicators

  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.033
  • wR factor = 0.087
  • Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing .. ?
Alert level B PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.66 Ratio
Author Response: see _publ_section_comment

Alert level C PLAT057_ALERT_3_C Correction for Absorption Required RT(exp) = 1.15 PLAT355_ALERT_3_C Long O-H Bond (0.82A) O2 - H4 = 1.04 Ang. PLAT417_ALERT_2_C Short Inter D-H..H-D H4 .. H4 = 2.10 Ang.
1 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1990); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1997-1999); program(s) used to solve structure: SIR92 (Altomare et al. 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN for Windows.

(I) top
Crystal data top
C7H4ClNO4F(000) = 408.00
Mr = 201.57Dx = 1.694 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 7.404 (3) Åθ = 11.8–12.4°
b = 5.6695 (9) ŵ = 0.46 mm1
c = 19.144 (3) ÅT = 297 K
β = 100.42 (2)°Prismatic, colorless
V = 790.4 (4) Å30.50 × 0.45 × 0.20 mm
Z = 4
Data collection top
Rigaku AFC-5R
diffractometer
1458 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anodeRint = 0.011
Graphite monochromatorθmax = 27.5°, θmin = 2.2°
ω–2θ scansh = 19
Absorption correction: ψ scan
(North et al., 1968)
k = 07
Tmin = 0.839, Tmax = 0.914l = 2424
2234 measured reflections3 standard reflections every 97 reflections
1815 independent reflections intensity decay: 3.3%
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)] = 0.033All H-atom parameters refined
wR(F2) = 0.087 w = 1/[σ2(Fo2) + (0.0175P)2 + 0.37P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
1815 reflectionsΔρmax = 0.27 e Å3
135 parametersΔρmin = 0.19 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraintsExtinction coefficient: 0.022 (2)
Special details top

Experimental. The scan width was (1.68 + 0.30tanθ)° with an ω scan speed of 6° per minute (up to 3 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

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
Cl0.10139 (7)0.37469 (9)0.68248 (3)0.04677 (17)
O10.28058 (19)0.4635 (3)0.51224 (8)0.0511 (4)
O20.52851 (18)0.2484 (3)0.55339 (8)0.0499 (4)
O30.4487 (2)0.4707 (3)0.69530 (8)0.0578 (4)
O40.2740 (2)0.3787 (3)0.77033 (8)0.0562 (4)
N0.3218 (2)0.3616 (3)0.71286 (8)0.0383 (4)
C10.2472 (2)0.1339 (3)0.58417 (9)0.0322 (4)
C20.3319 (2)0.0424 (3)0.62893 (9)0.0318 (4)
C30.2254 (2)0.1895 (3)0.66192 (9)0.0311 (4)
C40.0348 (2)0.1732 (3)0.64910 (9)0.0322 (4)
C50.0482 (2)0.0042 (3)0.60515 (10)0.0372 (4)
C60.0570 (3)0.1580 (3)0.57377 (10)0.0369 (4)
C70.3579 (2)0.2939 (3)0.54748 (9)0.0354 (4)
H10.458 (3)0.065 (3)0.6390 (10)0.035 (5)*
H20.179 (3)0.016 (4)0.5960 (11)0.049 (6)*
H30.001 (3)0.277 (4)0.5440 (10)0.043 (6)*
H40.592 (6)0.377 (7)0.528 (2)0.163 (17)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0395 (3)0.0464 (3)0.0569 (3)0.0088 (2)0.0154 (2)0.0081 (2)
O10.0406 (7)0.0521 (8)0.0612 (9)0.0039 (7)0.0105 (7)0.0268 (7)
O20.0350 (7)0.0506 (9)0.0665 (9)0.0040 (6)0.0157 (6)0.0220 (7)
O30.0561 (9)0.0504 (9)0.0658 (10)0.0214 (7)0.0082 (8)0.0084 (7)
O40.0517 (8)0.0719 (11)0.0453 (8)0.0004 (8)0.0097 (7)0.0244 (8)
N0.0347 (8)0.0341 (8)0.0440 (9)0.0018 (7)0.0016 (6)0.0072 (7)
C10.0326 (8)0.0328 (9)0.0315 (8)0.0007 (7)0.0062 (7)0.0020 (7)
C20.0278 (8)0.0331 (9)0.0343 (9)0.0004 (7)0.0048 (7)0.0016 (7)
C30.0326 (8)0.0296 (8)0.0303 (8)0.0011 (7)0.0039 (7)0.0010 (7)
C40.0327 (8)0.0325 (9)0.0331 (8)0.0037 (7)0.0107 (7)0.0019 (7)
C50.0277 (8)0.0440 (10)0.0402 (10)0.0032 (8)0.0070 (7)0.0030 (8)
C60.0348 (9)0.0385 (10)0.0374 (9)0.0064 (8)0.0064 (7)0.0071 (8)
C70.0335 (9)0.0371 (9)0.0353 (9)0.0008 (7)0.0052 (7)0.0047 (7)
Geometric parameters (Å, º) top
Cl—C41.7215 (18)C2—C31.377 (2)
C7—O11.252 (2)C3—C41.391 (2)
C7—O21.274 (2)C4—C51.382 (3)
N—O31.222 (2)C5—C61.378 (3)
N—O41.219 (2)C2—H10.93 (2)
N—C31.470 (2)C5—H20.95 (2)
C1—C21.390 (2)C6—H30.93 (2)
C1—C61.392 (3)O2—H41.04 (4)
C1—C71.482 (2)
Cl···O4i3.282 (2)O3···C7iv3.091 (3)
Cl···O4ii3.321 (2)O3···O4v3.084 (3)
O1···O2iii2.624 (2)O4···C5ii3.219 (3)
O3···C1iv3.260 (3)C6···C6vi3.322 (3)
O1—C7—O2123.54 (17)C2—C3—C4121.70 (16)
O1—C7—C1119.15 (16)C2—C3—N117.19 (15)
O2—C7—C1117.30 (16)C4—C3—N121.09 (15)
C7—O2—H4110 (2)C5—C4—C3118.77 (16)
O4—N—O3124.85 (16)C5—C4—Cl118.86 (14)
O4—N—C3117.80 (16)C3—C4—Cl122.29 (14)
O3—N—C3117.29 (15)C6—C5—C4120.10 (17)
C2—C1—C6119.38 (16)C6—C5—H2120.7 (13)
C2—C1—C7120.37 (16)C4—C5—H2119.2 (13)
C6—C1—C7120.25 (16)C5—C6—C1120.83 (17)
C3—C2—C1119.10 (16)C5—C6—H3120.2 (13)
C3—C2—H1117.4 (12)C1—C6—H3119.0 (13)
C1—C2—H1123.5 (12)
C6—C1—C2—C30.1 (3)N—C3—C4—Cl8.5 (2)
C7—C1—C2—C3179.55 (16)C3—C4—C5—C61.3 (3)
C1—C2—C3—C43.0 (3)Cl—C4—C5—C6175.54 (14)
C1—C2—C3—N175.53 (15)C4—C5—C6—C11.7 (3)
O4—N—C3—C2132.61 (18)C2—C1—C6—C52.4 (3)
O3—N—C3—C244.7 (2)C7—C1—C6—C5177.20 (17)
O4—N—C3—C445.9 (2)C2—C1—C7—O1174.02 (17)
O3—N—C3—C4136.79 (18)C6—C1—C7—O16.3 (3)
C2—C3—C4—C53.7 (3)C2—C1—C7—O26.5 (3)
N—C3—C4—C5174.78 (16)C6—C1—C7—O2173.11 (18)
C2—C3—C4—Cl173.02 (14)
Symmetry codes: (i) x, y1/2, z+3/2; (ii) x, y+1/2, z+3/2; (iii) x+1, y1, z+1; (iv) x, y+1, z; (v) x+1, y+1/2, z+3/2; (vi) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H4···O1iii1.04 (4)1.60 (4)2.624 (2)169 (4)
C5—H2···O2vii0.95 (2)2.54 (2)3.406 (3)150.8 (18)
Symmetry codes: (iii) x+1, y1, z+1; (vii) x1, y, 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