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The mol­ecule of the title compound, C14H11ClN2O3, is roughly planar and displays a trans configuration with respect to the C=N double bond. The crystal structure is stabilized by inter­molecular O—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806010798/rz2013sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806010798/rz2013Isup2.hkl
Contains datablock I

CCDC reference: 605164

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.073
  • wR factor = 0.153
  • Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.

(I) top
Crystal data top
C14H11ClN2O3F(000) = 600
Mr = 290.70Dx = 1.497 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 551 reflections
a = 18.873 (2) Åθ = 2.6–23.8°
b = 5.391 (1) ŵ = 0.31 mm1
c = 12.851 (3) ÅT = 298 K
β = 99.474 (4)°Flake, yellow
V = 1289.6 (4) Å30.14 × 0.09 × 0.01 mm
Z = 4
Data collection top
Bruker APEX area-detector
diffractometer
2650 independent reflections
Radiation source: fine-focus sealed tube1393 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.090
ω scanθmax = 26.5°, θmin = 1.1°
Absorption correction: multi-scan
SADABS (Sheldrick, 1996)
h = 2323
Tmin = 0.959, Tmax = 0.997k = 66
9927 measured reflectionsl = 1616
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)] = 0.073Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0266P)2 + 0.8881P]
where P = (Fo2 + 2Fc2)/3
2650 reflections(Δ/σ)max < 0.001
188 parametersΔρmax = 0.20 e Å3
2 restraintsΔρmin = 0.22 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
Cl10.03516 (7)1.3981 (2)0.82934 (9)0.0698 (4)
O10.20247 (19)0.7032 (7)1.1218 (2)0.0773 (11)
H10.22450.60261.09150.116*
O20.34974 (16)0.1630 (5)1.03772 (19)0.0587 (9)
O30.30762 (16)0.1941 (5)0.70983 (18)0.0499 (8)
N10.25516 (17)0.5195 (6)0.9530 (2)0.0412 (8)
N20.29197 (18)0.3662 (6)0.8949 (2)0.0430 (8)
C10.1714 (2)0.8570 (7)0.9427 (3)0.0426 (10)
C20.1660 (2)0.8595 (9)1.0505 (3)0.0555 (12)
C30.1208 (3)1.0289 (10)1.0863 (3)0.0743 (15)
H3A0.11741.03151.15760.089*
C40.0811 (3)1.1929 (9)1.0199 (4)0.0700 (15)
H40.05111.30611.04580.084*
C50.0859 (2)1.1890 (8)0.9147 (3)0.0501 (11)
C60.1307 (2)1.0260 (7)0.8762 (3)0.0484 (11)
H60.13401.02820.80480.058*
C70.2164 (2)0.6836 (7)0.8981 (3)0.0429 (10)
H70.21740.69130.82610.051*
C80.3367 (2)0.1901 (7)0.9418 (3)0.0391 (10)
C90.3705 (2)0.0257 (7)0.8710 (3)0.0342 (9)
C100.3555 (2)0.0264 (7)0.7604 (3)0.0358 (9)
C110.3867 (2)0.1494 (7)0.7036 (3)0.0472 (11)
H110.37480.15310.63050.057*
C120.4346 (2)0.3169 (8)0.7540 (3)0.0511 (11)
H120.45570.43220.71480.061*
C130.4521 (2)0.3168 (8)0.8629 (3)0.0534 (12)
H130.48490.43090.89710.064*
C140.4205 (2)0.1468 (7)0.9196 (3)0.0426 (10)
H140.43260.14590.99270.051*
H30.322 (2)0.225 (8)0.6478 (18)0.080*
H20.290 (2)0.387 (8)0.8250 (10)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0757 (9)0.0669 (8)0.0684 (8)0.0169 (7)0.0169 (6)0.0047 (6)
O10.092 (3)0.102 (3)0.0396 (17)0.040 (2)0.0156 (17)0.0028 (18)
O20.078 (2)0.075 (2)0.0227 (14)0.0151 (17)0.0095 (14)0.0033 (14)
O30.069 (2)0.0591 (19)0.0234 (14)0.0144 (16)0.0123 (14)0.0014 (13)
N10.042 (2)0.052 (2)0.0329 (17)0.0003 (18)0.0151 (15)0.0070 (16)
N20.052 (2)0.051 (2)0.0286 (17)0.0001 (18)0.0149 (17)0.0054 (17)
C10.045 (2)0.050 (3)0.033 (2)0.003 (2)0.0068 (19)0.008 (2)
C20.059 (3)0.072 (3)0.036 (2)0.011 (3)0.010 (2)0.006 (2)
C30.084 (4)0.103 (4)0.038 (2)0.031 (3)0.016 (3)0.010 (3)
C40.071 (4)0.084 (4)0.058 (3)0.024 (3)0.020 (3)0.013 (3)
C50.044 (3)0.058 (3)0.050 (3)0.005 (2)0.013 (2)0.004 (2)
C60.053 (3)0.053 (3)0.043 (2)0.005 (2)0.016 (2)0.007 (2)
C70.047 (3)0.052 (3)0.032 (2)0.007 (2)0.010 (2)0.008 (2)
C80.044 (2)0.047 (3)0.029 (2)0.008 (2)0.0119 (18)0.0063 (19)
C90.041 (2)0.037 (2)0.0260 (19)0.0094 (19)0.0086 (16)0.0003 (17)
C100.042 (2)0.038 (2)0.0276 (19)0.0028 (19)0.0068 (17)0.0040 (18)
C110.056 (3)0.056 (3)0.030 (2)0.004 (2)0.009 (2)0.010 (2)
C120.057 (3)0.052 (3)0.047 (3)0.007 (2)0.016 (2)0.004 (2)
C130.062 (3)0.050 (3)0.048 (3)0.008 (2)0.007 (2)0.014 (2)
C140.051 (3)0.050 (3)0.027 (2)0.005 (2)0.0064 (19)0.0049 (19)
Geometric parameters (Å, º) top
Cl1—C51.746 (4)C4—C51.370 (6)
O1—C21.347 (5)C4—H40.9300
O1—H10.8200C5—C61.367 (5)
O2—C81.226 (4)C6—H60.9300
O3—C101.365 (4)C7—H70.9300
O3—H30.90 (3)C8—C91.487 (5)
N1—C71.283 (4)C9—C141.397 (5)
N1—N21.376 (4)C9—C101.402 (5)
N2—C81.345 (5)C10—C111.385 (5)
N2—H20.900 (10)C11—C121.364 (5)
C1—C61.391 (5)C11—H110.9300
C1—C21.406 (5)C12—C131.384 (5)
C1—C71.445 (5)C12—H120.9300
C2—C31.379 (6)C13—C141.368 (5)
C3—C41.364 (6)C13—H130.9300
C3—H3A0.9300C14—H140.9300
C2—O1—H1109.5N1—C7—C1123.2 (3)
C10—O3—H3106 (3)N1—C7—H7118.4
C7—N1—N2114.1 (3)C1—C7—H7118.4
C8—N2—N1121.0 (3)O2—C8—N2122.8 (4)
C8—N2—H2117 (3)O2—C8—C9120.6 (4)
N1—N2—H2122 (3)N2—C8—C9116.6 (3)
C6—C1—C2118.6 (4)C14—C9—C10117.6 (3)
C6—C1—C7118.7 (3)C14—C9—C8116.7 (3)
C2—C1—C7122.7 (4)C10—C9—C8125.7 (3)
O1—C2—C3117.6 (4)O3—C10—C11120.5 (3)
O1—C2—C1123.5 (4)O3—C10—C9119.4 (3)
C3—C2—C1118.9 (4)C11—C10—C9120.0 (4)
C4—C3—C2121.8 (4)C12—C11—C10120.6 (4)
C4—C3—H3A119.1C12—C11—H11119.7
C2—C3—H3A119.1C10—C11—H11119.7
C3—C4—C5119.2 (4)C11—C12—C13120.6 (4)
C3—C4—H4120.4C11—C12—H12119.7
C5—C4—H4120.4C13—C12—H12119.7
C6—C5—C4120.9 (4)C14—C13—C12119.2 (4)
C6—C5—Cl1119.7 (3)C14—C13—H13120.4
C4—C5—Cl1119.4 (3)C12—C13—H13120.4
C5—C6—C1120.6 (4)C13—C14—C9122.0 (3)
C5—C6—H6119.7C13—C14—H14119.0
C1—C6—H6119.7C9—C14—H14119.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O30.90 (1)1.88 (3)2.614 (4)137 (4)
O3—H3···O2i0.90 (3)1.70 (3)2.588 (3)170 (4)
O1—H1···O3ii0.822.563.011 (4)116
O1—H1···N10.822.012.717 (4)144
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y+1/2, z+1/2.
 

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