The molecule of the title compound, C
14H
11ClN
2O
3, 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
CCDC reference: 605164
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
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.
Crystal data top
C14H11ClN2O3 | F(000) = 600 |
Mr = 290.70 | Dx = 1.497 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 551 reflections |
a = 18.873 (2) Å | θ = 2.6–23.8° |
b = 5.391 (1) Å | µ = 0.31 mm−1 |
c = 12.851 (3) Å | T = 298 K |
β = 99.474 (4)° | Flake, yellow |
V = 1289.6 (4) Å3 | 0.14 × 0.09 × 0.01 mm |
Z = 4 | |
Data collection top
Bruker APEX area-detector diffractometer | 2650 independent reflections |
Radiation source: fine-focus sealed tube | 1393 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.090 |
ω scan | θmax = 26.5°, θmin = 1.1° |
Absorption correction: multi-scan SADABS (Sheldrick, 1996) | h = −23→23 |
Tmin = 0.959, Tmax = 0.997 | k = −6→6 |
9927 measured reflections | l = −16→16 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.073 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.153 | H 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 parameters | Δρmax = 0.20 e Å−3 |
2 restraints | Δρmin = −0.22 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Cl1 | 0.03516 (7) | 1.3981 (2) | 0.82934 (9) | 0.0698 (4) | |
O1 | 0.20247 (19) | 0.7032 (7) | 1.1218 (2) | 0.0773 (11) | |
H1 | 0.2245 | 0.6026 | 1.0915 | 0.116* | |
O2 | 0.34974 (16) | 0.1630 (5) | 1.03772 (19) | 0.0587 (9) | |
O3 | 0.30762 (16) | 0.1941 (5) | 0.70983 (18) | 0.0499 (8) | |
N1 | 0.25516 (17) | 0.5195 (6) | 0.9530 (2) | 0.0412 (8) | |
N2 | 0.29197 (18) | 0.3662 (6) | 0.8949 (2) | 0.0430 (8) | |
C1 | 0.1714 (2) | 0.8570 (7) | 0.9427 (3) | 0.0426 (10) | |
C2 | 0.1660 (2) | 0.8595 (9) | 1.0505 (3) | 0.0555 (12) | |
C3 | 0.1208 (3) | 1.0289 (10) | 1.0863 (3) | 0.0743 (15) | |
H3A | 0.1174 | 1.0315 | 1.1576 | 0.089* | |
C4 | 0.0811 (3) | 1.1929 (9) | 1.0199 (4) | 0.0700 (15) | |
H4 | 0.0511 | 1.3061 | 1.0458 | 0.084* | |
C5 | 0.0859 (2) | 1.1890 (8) | 0.9147 (3) | 0.0501 (11) | |
C6 | 0.1307 (2) | 1.0260 (7) | 0.8762 (3) | 0.0484 (11) | |
H6 | 0.1340 | 1.0282 | 0.8048 | 0.058* | |
C7 | 0.2164 (2) | 0.6836 (7) | 0.8981 (3) | 0.0429 (10) | |
H7 | 0.2174 | 0.6913 | 0.8261 | 0.051* | |
C8 | 0.3367 (2) | 0.1901 (7) | 0.9418 (3) | 0.0391 (10) | |
C9 | 0.3705 (2) | 0.0257 (7) | 0.8710 (3) | 0.0342 (9) | |
C10 | 0.3555 (2) | 0.0264 (7) | 0.7604 (3) | 0.0358 (9) | |
C11 | 0.3867 (2) | −0.1494 (7) | 0.7036 (3) | 0.0472 (11) | |
H11 | 0.3748 | −0.1531 | 0.6305 | 0.057* | |
C12 | 0.4346 (2) | −0.3169 (8) | 0.7540 (3) | 0.0511 (11) | |
H12 | 0.4557 | −0.4322 | 0.7148 | 0.061* | |
C13 | 0.4521 (2) | −0.3168 (8) | 0.8629 (3) | 0.0534 (12) | |
H13 | 0.4849 | −0.4309 | 0.8971 | 0.064* | |
C14 | 0.4205 (2) | −0.1468 (7) | 0.9196 (3) | 0.0426 (10) | |
H14 | 0.4326 | −0.1459 | 0.9927 | 0.051* | |
H3 | 0.322 (2) | 0.225 (8) | 0.6478 (18) | 0.080* | |
H2 | 0.290 (2) | 0.387 (8) | 0.8250 (10) | 0.080* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0757 (9) | 0.0669 (8) | 0.0684 (8) | 0.0169 (7) | 0.0169 (6) | 0.0047 (6) |
O1 | 0.092 (3) | 0.102 (3) | 0.0396 (17) | 0.040 (2) | 0.0156 (17) | 0.0028 (18) |
O2 | 0.078 (2) | 0.075 (2) | 0.0227 (14) | 0.0151 (17) | 0.0095 (14) | −0.0033 (14) |
O3 | 0.069 (2) | 0.0591 (19) | 0.0234 (14) | 0.0144 (16) | 0.0123 (14) | 0.0014 (13) |
N1 | 0.042 (2) | 0.052 (2) | 0.0329 (17) | −0.0003 (18) | 0.0151 (15) | −0.0070 (16) |
N2 | 0.052 (2) | 0.051 (2) | 0.0286 (17) | 0.0001 (18) | 0.0149 (17) | −0.0054 (17) |
C1 | 0.045 (2) | 0.050 (3) | 0.033 (2) | −0.003 (2) | 0.0068 (19) | −0.008 (2) |
C2 | 0.059 (3) | 0.072 (3) | 0.036 (2) | 0.011 (3) | 0.010 (2) | −0.006 (2) |
C3 | 0.084 (4) | 0.103 (4) | 0.038 (2) | 0.031 (3) | 0.016 (3) | −0.010 (3) |
C4 | 0.071 (4) | 0.084 (4) | 0.058 (3) | 0.024 (3) | 0.020 (3) | −0.013 (3) |
C5 | 0.044 (3) | 0.058 (3) | 0.050 (3) | 0.005 (2) | 0.013 (2) | −0.004 (2) |
C6 | 0.053 (3) | 0.053 (3) | 0.043 (2) | −0.005 (2) | 0.016 (2) | −0.007 (2) |
C7 | 0.047 (3) | 0.052 (3) | 0.032 (2) | −0.007 (2) | 0.010 (2) | −0.008 (2) |
C8 | 0.044 (2) | 0.047 (3) | 0.029 (2) | −0.008 (2) | 0.0119 (18) | −0.0063 (19) |
C9 | 0.041 (2) | 0.037 (2) | 0.0260 (19) | −0.0094 (19) | 0.0086 (16) | 0.0003 (17) |
C10 | 0.042 (2) | 0.038 (2) | 0.0276 (19) | −0.0028 (19) | 0.0068 (17) | 0.0040 (18) |
C11 | 0.056 (3) | 0.056 (3) | 0.030 (2) | 0.004 (2) | 0.009 (2) | −0.010 (2) |
C12 | 0.057 (3) | 0.052 (3) | 0.047 (3) | 0.007 (2) | 0.016 (2) | −0.004 (2) |
C13 | 0.062 (3) | 0.050 (3) | 0.048 (3) | 0.008 (2) | 0.007 (2) | 0.014 (2) |
C14 | 0.051 (3) | 0.050 (3) | 0.027 (2) | −0.005 (2) | 0.0064 (19) | 0.0049 (19) |
Geometric parameters (Å, º) top
Cl1—C5 | 1.746 (4) | C4—C5 | 1.370 (6) |
O1—C2 | 1.347 (5) | C4—H4 | 0.9300 |
O1—H1 | 0.8200 | C5—C6 | 1.367 (5) |
O2—C8 | 1.226 (4) | C6—H6 | 0.9300 |
O3—C10 | 1.365 (4) | C7—H7 | 0.9300 |
O3—H3 | 0.90 (3) | C8—C9 | 1.487 (5) |
N1—C7 | 1.283 (4) | C9—C14 | 1.397 (5) |
N1—N2 | 1.376 (4) | C9—C10 | 1.402 (5) |
N2—C8 | 1.345 (5) | C10—C11 | 1.385 (5) |
N2—H2 | 0.900 (10) | C11—C12 | 1.364 (5) |
C1—C6 | 1.391 (5) | C11—H11 | 0.9300 |
C1—C2 | 1.406 (5) | C12—C13 | 1.384 (5) |
C1—C7 | 1.445 (5) | C12—H12 | 0.9300 |
C2—C3 | 1.379 (6) | C13—C14 | 1.368 (5) |
C3—C4 | 1.364 (6) | C13—H13 | 0.9300 |
C3—H3A | 0.9300 | C14—H14 | 0.9300 |
| | | |
C2—O1—H1 | 109.5 | N1—C7—C1 | 123.2 (3) |
C10—O3—H3 | 106 (3) | N1—C7—H7 | 118.4 |
C7—N1—N2 | 114.1 (3) | C1—C7—H7 | 118.4 |
C8—N2—N1 | 121.0 (3) | O2—C8—N2 | 122.8 (4) |
C8—N2—H2 | 117 (3) | O2—C8—C9 | 120.6 (4) |
N1—N2—H2 | 122 (3) | N2—C8—C9 | 116.6 (3) |
C6—C1—C2 | 118.6 (4) | C14—C9—C10 | 117.6 (3) |
C6—C1—C7 | 118.7 (3) | C14—C9—C8 | 116.7 (3) |
C2—C1—C7 | 122.7 (4) | C10—C9—C8 | 125.7 (3) |
O1—C2—C3 | 117.6 (4) | O3—C10—C11 | 120.5 (3) |
O1—C2—C1 | 123.5 (4) | O3—C10—C9 | 119.4 (3) |
C3—C2—C1 | 118.9 (4) | C11—C10—C9 | 120.0 (4) |
C4—C3—C2 | 121.8 (4) | C12—C11—C10 | 120.6 (4) |
C4—C3—H3A | 119.1 | C12—C11—H11 | 119.7 |
C2—C3—H3A | 119.1 | C10—C11—H11 | 119.7 |
C3—C4—C5 | 119.2 (4) | C11—C12—C13 | 120.6 (4) |
C3—C4—H4 | 120.4 | C11—C12—H12 | 119.7 |
C5—C4—H4 | 120.4 | C13—C12—H12 | 119.7 |
C6—C5—C4 | 120.9 (4) | C14—C13—C12 | 119.2 (4) |
C6—C5—Cl1 | 119.7 (3) | C14—C13—H13 | 120.4 |
C4—C5—Cl1 | 119.4 (3) | C12—C13—H13 | 120.4 |
C5—C6—C1 | 120.6 (4) | C13—C14—C9 | 122.0 (3) |
C5—C6—H6 | 119.7 | C13—C14—H14 | 119.0 |
C1—C6—H6 | 119.7 | C9—C14—H14 | 119.0 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O3 | 0.90 (1) | 1.88 (3) | 2.614 (4) | 137 (4) |
O3—H3···O2i | 0.90 (3) | 1.70 (3) | 2.588 (3) | 170 (4) |
O1—H1···O3ii | 0.82 | 2.56 | 3.011 (4) | 116 |
O1—H1···N1 | 0.82 | 2.01 | 2.717 (4) | 144 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2. |