Download citation
Download citation
link to html
The molecule of the title compound, C9H7ClN2O2, is essentially planar except for H atoms, and the occurrence of O—H...N hydrogen-bonding inter­actions results in the formation of a dimer.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806024433/dn2054sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806024433/dn2054Isup2.hkl
Contains datablock I

CCDC reference: 624201

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.010 Å
  • R factor = 0.066
  • wR factor = 0.149
  • Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 25.99 From the CIF: _diffrn_reflns_theta_full 25.99 From the CIF: _reflns_number_total 1746 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 1856 Completeness (_total/calc) 94.07% PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.94 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 40 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 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 4 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: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens,1996) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXS97.

[3-(4-Chlorophenyl)-1,2,4-oxadiazol-5-yl]methanol top
Crystal data top
C9H7ClN2O2F(000) = 864
Mr = 210.62Dx = 1.475 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 25 reflections
a = 27.789 (2) Åθ = 9–11°
b = 4.0141 (5) ŵ = 0.38 mm1
c = 21.4570 (15) ÅT = 293 K
β = 127.56 (3)°Block, colourless
V = 1897.4 (8) Å30.20 × 0.10 × 0.10 mm
Z = 8
Data collection top
Enraf–Nonius CAD-4
diffractometer
698 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.053
Graphite monochromatorθmax = 26.0°, θmin = 1.9°
ω/2θ scansh = 3426
Absorption correction: ψ scan
(North et al., 1968)
k = 04
Tmin = 0.929, Tmax = 0.963l = 026
1746 measured reflections3 standard reflections every 200 reflections
1746 independent reflections intensity decay: none
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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.03P)2 + 2P]
where P = (Fo2 + 2Fc2)/3
1746 reflections(Δ/σ)max < 0.001
130 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.14 e Å3
Special details top

Experimental. 1H NMR (CDCl3): δ 7.80–8.02 (s, 2H), 7.45–7.47 (s, 2H), 4.96 (s, 2H), 2.86 (w, 1H).

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
Cl0.22383 (7)0.3303 (5)0.19207 (10)0.1168 (7)
O10.57455 (16)0.0814 (12)0.1728 (2)0.0933 (13)
O20.5716 (2)0.4789 (12)0.3012 (3)0.0991 (15)
N10.5237 (2)0.1959 (14)0.0977 (3)0.0951 (16)
N20.49330 (19)0.1140 (12)0.1556 (3)0.0796 (13)
C10.2970 (3)0.2514 (17)0.1106 (4)0.0929 (19)
C20.3450 (3)0.3529 (17)0.1091 (3)0.0952 (19)
H2C0.33790.46020.15240.114*
C30.4039 (2)0.2945 (17)0.0428 (3)0.0897 (18)
H3A0.43630.36580.04150.108*
C40.4150 (3)0.1310 (17)0.0217 (3)0.0827 (16)
C50.3658 (3)0.0226 (17)0.0182 (3)0.097 (2)
H5A0.37250.09190.06050.116*
C60.3070 (3)0.0846 (18)0.0481 (4)0.099 (2)
H6A0.27430.01270.05000.119*
C70.4782 (2)0.0707 (15)0.0919 (3)0.0774 (15)
C80.5516 (3)0.0955 (16)0.2024 (3)0.0843 (17)
C90.5970 (2)0.2373 (16)0.2818 (3)0.0908 (18)
H9A0.62980.33690.28400.109*
H9B0.61400.05930.32040.109*
H0.555 (3)0.368 (17)0.316 (3)0.109*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0821 (10)0.1361 (15)0.1023 (12)0.0064 (12)0.0408 (9)0.0006 (13)
O10.067 (2)0.129 (4)0.082 (3)0.001 (3)0.045 (2)0.002 (3)
O20.097 (3)0.101 (4)0.107 (3)0.006 (3)0.066 (3)0.005 (3)
N10.084 (3)0.118 (4)0.087 (3)0.010 (3)0.054 (3)0.001 (3)
N20.071 (3)0.082 (3)0.085 (3)0.006 (3)0.047 (3)0.007 (3)
C10.080 (4)0.104 (5)0.090 (4)0.001 (4)0.049 (4)0.005 (4)
C20.088 (4)0.114 (5)0.082 (4)0.002 (4)0.051 (4)0.001 (4)
C30.074 (4)0.110 (5)0.085 (4)0.005 (4)0.048 (3)0.006 (4)
C40.079 (4)0.094 (4)0.074 (4)0.001 (3)0.046 (3)0.002 (3)
C50.090 (4)0.124 (6)0.080 (4)0.010 (4)0.053 (4)0.002 (4)
C60.074 (4)0.116 (6)0.099 (5)0.013 (4)0.049 (4)0.006 (4)
C70.078 (4)0.085 (4)0.082 (4)0.009 (3)0.055 (3)0.006 (3)
C80.082 (4)0.088 (4)0.091 (4)0.000 (4)0.057 (4)0.002 (4)
C90.082 (4)0.095 (5)0.093 (4)0.005 (4)0.052 (4)0.001 (4)
Geometric parameters (Å, º) top
Cl—C11.720 (6)C2—H2C0.9300
O1—C81.344 (6)C3—C41.386 (7)
O1—N11.424 (5)C3—H3A0.9300
O2—C91.403 (7)C4—C51.391 (7)
O2—H0.83 (6)C4—C71.479 (7)
N1—C71.293 (6)C5—C61.386 (7)
N2—C81.287 (6)C5—H5A0.9300
N2—C71.377 (6)C6—H6A0.9300
C1—C61.368 (8)C8—C91.483 (7)
C1—C21.375 (7)C9—H9A0.9700
C2—C31.386 (7)C9—H9B0.9700
C8—O1—N1106.0 (4)C6—C5—H5A119.9
C9—O2—H104 (5)C4—C5—H5A119.9
C7—N1—O1102.8 (5)C1—C6—C5120.1 (6)
C8—N2—C7102.7 (5)C1—C6—H6A120.0
C6—C1—C2120.5 (6)C5—C6—H6A120.0
C6—C1—Cl119.6 (5)N1—C7—N2115.2 (5)
C2—C1—Cl119.8 (5)N1—C7—C4121.3 (6)
C1—C2—C3119.7 (6)N2—C7—C4123.5 (5)
C1—C2—H2C120.2N2—C8—O1113.4 (5)
C3—C2—H2C120.2N2—C8—C9131.2 (6)
C4—C3—C2120.6 (6)O1—C8—C9115.5 (5)
C4—C3—H3A119.7O2—C9—C8112.1 (5)
C2—C3—H3A119.7O2—C9—H9A109.2
C3—C4—C5118.7 (5)C8—C9—H9A109.2
C3—C4—C7119.8 (5)O2—C9—H9B109.2
C5—C4—C7121.5 (6)C8—C9—H9B109.2
C6—C5—C4120.3 (6)H9A—C9—H9B107.9
C8—O1—N1—C71.0 (6)C8—N2—C7—N10.3 (7)
C6—C1—C2—C32.0 (10)C8—N2—C7—C4178.7 (6)
Cl—C1—C2—C3178.8 (5)C3—C4—C7—N16.9 (9)
C1—C2—C3—C40.8 (10)C5—C4—C7—N1174.1 (6)
C2—C3—C4—C50.8 (10)C3—C4—C7—N2174.3 (6)
C2—C3—C4—C7179.9 (6)C5—C4—C7—N24.8 (9)
C3—C4—C5—C61.4 (10)C7—N2—C8—O11.0 (7)
C7—C4—C5—C6179.5 (6)C7—N2—C8—C9179.7 (6)
C2—C1—C6—C51.4 (10)N1—O1—C8—N21.3 (7)
Cl—C1—C6—C5179.4 (5)N1—O1—C8—C9179.2 (5)
C4—C5—C6—C10.3 (10)N2—C8—C9—O213.2 (9)
O1—N1—C7—N20.5 (7)O1—C8—C9—O2166.1 (5)
O1—N1—C7—C4179.4 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H···N2i0.83 (8)2.05 (9)2.880 (9)175 (8)
C9—H9B···O2ii0.972.533.209 (8)127
Symmetry codes: (i) x+1, y, z+1/2; (ii) x, y+1, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds