Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807006538/dn3038sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807006538/dn3038Isup2.hkl |
CCDC reference: 600063
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.002 Å
- R factor = 0.045
- wR factor = 0.121
- Data-to-parameter ratio = 22.0
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT430_ALERT_2_B Short Inter D...A Contact O3 .. O3 .. 2.69 Ang.
Alert level C PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C18H11ClN2O4 | F(000) = 728 |
Mr = 354.74 | Dx = 1.482 Mg m−3 |
Monoclinic, P21/c | Melting point: 464 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 5.8222 (1) Å | Cell parameters from 3811 reflections |
b = 19.1260 (3) Å | θ = 2.1–30.9° |
c = 14.3158 (2) Å | µ = 0.27 mm−1 |
β = 93.922 (1)° | T = 295 K |
V = 1590.41 (4) Å3 | Prism, yellow |
Z = 4 | 0.40 × 0.32 × 0.23 mm |
Bruker SMART APEX CCD area-detector diffractometer | 4999 independent reflections |
Radiation source: fine-focus sealed tube | 2944 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
φ and ω scans | θmax = 30.9°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2005) | h = −8→8 |
Tmin = 0.901, Tmax = 0.941 | k = −19→27 |
19802 measured reflections | l = −20→20 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0509P)2 + 0.2462P] where P = (Fo2 + 2Fc2)/3 |
4999 reflections | (Δ/σ)max = 0.001 |
227 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
Experimental. The UV spectrum of the molecule in anhydrous ethanol exhibited two absorption bands at 201 nm and 272 nm assigned to intramolecular π -π* and n-π* transitions respectively fromaryl ring·The IR spectrum indicated a very strong asymmetric C=O strectching frequency at 1607 cm-1 and 1527 cm-1 for the pyrazolone ring. Vibrational frequency bands due to intermolecular hydrogen bond O—H···O group of the ligand observed at 3118 cm-1. This analysis result pointed out the ligand existence of enol form in solid state and ethanol solution. However, the 1H NMR data, showed that in CDCl3 solution the ligand exists in keto form·From thermal analysis curves (TG-DTA) of the title compound, an endothermic peak at 160 oC is attributed to the phase transition temperature of the compound. It is thermally stable up to approximately 180 oC and can be completely decomposed at about 670 oC in an air atmosphere, the finally decomposition product is carbon dioxide and water. 1H NMR (CDCl3): δ 6.47 (q, 1H), 6.52 (q, 1H), 6.70 (d, 1H), 6.80 (d, 1H), 7.25 (s, 1H), 7.40 (d, 2H), 7.46 (d, 2H), 7.89 (s, 2H). MS (ESI), m/z (%): 355/353 (70/100, M+). 305 (27), 287 (6). |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | −0.16695 (9) | 0.53955 (3) | 0.89633 (3) | 0.06853 (17) | |
O1 | 0.6637 (2) | 0.49394 (6) | 0.59135 (8) | 0.0482 (3) | |
H1 | 0.7810 | 0.5005 | 0.5640 | 0.072* | |
O2 | 0.7415 (2) | 0.21465 (6) | 0.50733 (8) | 0.0530 (3) | |
O3 | 1.0034 (2) | 0.43071 (7) | 0.48386 (9) | 0.0600 (3) | |
O4 | 0.6943 (2) | 0.30827 (7) | 0.34199 (8) | 0.0642 (4) | |
N1 | 0.4254 (2) | 0.40307 (7) | 0.62999 (9) | 0.0412 (3) | |
N2 | 0.3823 (2) | 0.33331 (7) | 0.60881 (9) | 0.0445 (3) | |
C1 | 0.0126 (3) | 0.49871 (9) | 0.82043 (11) | 0.0481 (4) | |
C2 | 0.2134 (3) | 0.53072 (10) | 0.79972 (12) | 0.0531 (4) | |
H2 | 0.2562 | 0.5730 | 0.8280 | 0.064* | |
C3 | 0.3527 (3) | 0.49992 (9) | 0.73647 (12) | 0.0506 (4) | |
H3 | 0.4886 | 0.5216 | 0.7218 | 0.061* | |
C4 | 0.2881 (3) | 0.43689 (8) | 0.69544 (10) | 0.0408 (3) | |
C5 | 0.0869 (3) | 0.40435 (9) | 0.71839 (11) | 0.0472 (4) | |
H5 | 0.0447 | 0.3616 | 0.6915 | 0.057* | |
C6 | −0.0505 (3) | 0.43551 (10) | 0.78115 (11) | 0.0509 (4) | |
H6 | −0.1856 | 0.4138 | 0.7968 | 0.061* | |
C7 | 0.6003 (3) | 0.42782 (8) | 0.58177 (10) | 0.0396 (3) | |
C8 | 0.6731 (3) | 0.37420 (8) | 0.52519 (10) | 0.0397 (3) | |
C9 | 0.5283 (3) | 0.31681 (8) | 0.54557 (10) | 0.0405 (3) | |
C10 | 0.5303 (3) | 0.24502 (8) | 0.51172 (10) | 0.0426 (4) | |
C11 | 0.3650 (3) | 0.20013 (10) | 0.48274 (14) | 0.0586 (5) | |
H11 | 0.2073 | 0.2084 | 0.4795 | 0.070* | |
C12 | 0.4750 (4) | 0.13735 (10) | 0.45775 (14) | 0.0619 (5) | |
H12 | 0.4044 | 0.0967 | 0.4346 | 0.074* | |
C13 | 0.6993 (4) | 0.14837 (10) | 0.47415 (13) | 0.0604 (5) | |
H13 | 0.8127 | 0.1155 | 0.4644 | 0.072* | |
C14 | 0.7645 (5) | 0.27630 (12) | 0.26390 (14) | 0.0803 (7) | |
H14 | 0.6706 | 0.2486 | 0.2239 | 0.096* | |
C15 | 0.9838 (5) | 0.28975 (12) | 0.25236 (15) | 0.0811 (7) | |
H15 | 1.0690 | 0.2738 | 0.2040 | 0.097* | |
C16 | 1.0631 (4) | 0.33308 (11) | 0.32800 (13) | 0.0606 (5) | |
H16 | 1.2105 | 0.3514 | 0.3391 | 0.073* | |
C17 | 0.8832 (3) | 0.34245 (9) | 0.38043 (11) | 0.0451 (4) | |
C18 | 0.8612 (3) | 0.38416 (8) | 0.46469 (10) | 0.0417 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0562 (3) | 0.0872 (4) | 0.0640 (3) | 0.0099 (3) | 0.0171 (2) | −0.0242 (2) |
O1 | 0.0518 (7) | 0.0417 (6) | 0.0526 (6) | −0.0084 (5) | 0.0156 (5) | −0.0039 (5) |
O2 | 0.0492 (7) | 0.0496 (7) | 0.0603 (7) | 0.0098 (6) | 0.0047 (5) | −0.0064 (5) |
O3 | 0.0628 (8) | 0.0574 (8) | 0.0622 (7) | −0.0208 (7) | 0.0213 (6) | −0.0092 (6) |
O4 | 0.0722 (9) | 0.0733 (9) | 0.0473 (6) | −0.0143 (7) | 0.0066 (6) | −0.0079 (6) |
N1 | 0.0420 (7) | 0.0371 (7) | 0.0457 (6) | −0.0009 (6) | 0.0110 (5) | −0.0025 (5) |
N2 | 0.0467 (8) | 0.0371 (7) | 0.0511 (7) | −0.0008 (6) | 0.0130 (6) | −0.0016 (6) |
C1 | 0.0451 (9) | 0.0570 (10) | 0.0427 (7) | 0.0116 (8) | 0.0073 (7) | −0.0048 (7) |
C2 | 0.0557 (11) | 0.0470 (10) | 0.0575 (9) | 0.0023 (8) | 0.0103 (8) | −0.0112 (8) |
C3 | 0.0470 (9) | 0.0464 (9) | 0.0597 (9) | −0.0031 (8) | 0.0136 (8) | −0.0065 (8) |
C4 | 0.0417 (8) | 0.0412 (8) | 0.0403 (7) | 0.0042 (7) | 0.0080 (6) | 0.0005 (6) |
C5 | 0.0479 (9) | 0.0473 (9) | 0.0473 (8) | −0.0026 (8) | 0.0097 (7) | −0.0049 (7) |
C6 | 0.0420 (9) | 0.0621 (11) | 0.0496 (8) | −0.0038 (8) | 0.0116 (7) | −0.0032 (8) |
C7 | 0.0406 (8) | 0.0394 (8) | 0.0391 (7) | −0.0004 (7) | 0.0053 (6) | 0.0015 (6) |
C8 | 0.0409 (8) | 0.0397 (8) | 0.0390 (7) | 0.0005 (7) | 0.0057 (6) | −0.0002 (6) |
C9 | 0.0406 (8) | 0.0394 (8) | 0.0419 (7) | 0.0013 (7) | 0.0057 (6) | 0.0019 (6) |
C10 | 0.0445 (9) | 0.0406 (8) | 0.0441 (7) | 0.0024 (7) | 0.0124 (6) | 0.0024 (7) |
C11 | 0.0497 (10) | 0.0483 (10) | 0.0799 (12) | −0.0068 (9) | 0.0186 (9) | −0.0062 (9) |
C12 | 0.0742 (14) | 0.0425 (10) | 0.0713 (12) | −0.0096 (9) | 0.0231 (10) | −0.0072 (9) |
C13 | 0.0771 (14) | 0.0443 (10) | 0.0613 (10) | 0.0139 (10) | 0.0159 (10) | −0.0045 (8) |
C14 | 0.123 (2) | 0.0687 (14) | 0.0505 (10) | −0.0167 (14) | 0.0139 (12) | −0.0143 (10) |
C15 | 0.122 (2) | 0.0661 (14) | 0.0597 (11) | 0.0124 (14) | 0.0409 (13) | −0.0070 (10) |
C16 | 0.0620 (12) | 0.0626 (11) | 0.0598 (10) | 0.0061 (10) | 0.0238 (9) | 0.0033 (9) |
C17 | 0.0507 (10) | 0.0431 (9) | 0.0423 (7) | −0.0007 (8) | 0.0098 (7) | 0.0020 (7) |
C18 | 0.0436 (9) | 0.0409 (8) | 0.0414 (7) | 0.0004 (7) | 0.0076 (6) | 0.0030 (6) |
Cl1—C1 | 1.7435 (16) | C5—H5 | 0.9300 |
O1—C7 | 1.3219 (19) | C6—H6 | 0.9300 |
O1—H1 | 0.8200 | C7—C8 | 1.391 (2) |
O2—C10 | 1.3655 (19) | C8—C9 | 1.426 (2) |
O2—C13 | 1.370 (2) | C8—C18 | 1.454 (2) |
O3—C18 | 1.2338 (19) | C9—C10 | 1.456 (2) |
O4—C14 | 1.361 (2) | C10—C11 | 1.334 (2) |
O4—C17 | 1.363 (2) | C11—C12 | 1.418 (3) |
N1—C7 | 1.3541 (19) | C11—H11 | 0.9300 |
N1—N2 | 1.3874 (18) | C12—C13 | 1.327 (3) |
N1—C4 | 1.4273 (18) | C12—H12 | 0.9300 |
N2—C9 | 1.3216 (19) | C13—H13 | 0.9300 |
C1—C2 | 1.370 (3) | C14—C15 | 1.324 (3) |
C1—C6 | 1.373 (3) | C14—H14 | 0.9300 |
C2—C3 | 1.387 (2) | C15—C16 | 1.416 (3) |
C2—H2 | 0.9300 | C15—H15 | 0.9300 |
C3—C4 | 1.382 (2) | C16—C17 | 1.342 (2) |
C3—H3 | 0.9300 | C16—H16 | 0.9300 |
C4—C5 | 1.386 (2) | C17—C18 | 1.459 (2) |
C5—C6 | 1.379 (2) | ||
C7—O1—H1 | 109.5 | N2—C9—C8 | 111.92 (13) |
C10—O2—C13 | 105.59 (14) | N2—C9—C10 | 118.24 (14) |
C14—O4—C17 | 105.53 (16) | C8—C9—C10 | 129.73 (14) |
C7—N1—N2 | 110.84 (12) | C11—C10—O2 | 110.14 (14) |
C7—N1—C4 | 130.59 (13) | C11—C10—C9 | 133.49 (16) |
N2—N1—C4 | 118.58 (12) | O2—C10—C9 | 116.37 (14) |
C9—N2—N1 | 105.33 (12) | C10—C11—C12 | 107.15 (17) |
C2—C1—C6 | 120.91 (15) | C10—C11—H11 | 126.4 |
C2—C1—Cl1 | 119.45 (14) | C12—C11—H11 | 126.4 |
C6—C1—Cl1 | 119.64 (13) | C13—C12—C11 | 106.06 (17) |
C1—C2—C3 | 119.80 (16) | C13—C12—H12 | 127.0 |
C1—C2—H2 | 120.1 | C11—C12—H12 | 127.0 |
C3—C2—H2 | 120.1 | C12—C13—O2 | 111.06 (17) |
C4—C3—C2 | 119.58 (16) | C12—C13—H13 | 124.5 |
C4—C3—H3 | 120.2 | O2—C13—H13 | 124.5 |
C2—C3—H3 | 120.2 | C15—C14—O4 | 111.2 (2) |
C3—C4—C5 | 120.05 (14) | C15—C14—H14 | 124.4 |
C3—C4—N1 | 121.75 (14) | O4—C14—H14 | 124.4 |
C5—C4—N1 | 118.19 (14) | C14—C15—C16 | 106.58 (18) |
C6—C5—C4 | 119.88 (16) | C14—C15—H15 | 126.7 |
C6—C5—H5 | 120.1 | C16—C15—H15 | 126.7 |
C4—C5—H5 | 120.1 | C17—C16—C15 | 106.23 (19) |
C1—C6—C5 | 119.75 (16) | C17—C16—H16 | 126.9 |
C1—C6—H6 | 120.1 | C15—C16—H16 | 126.9 |
C5—C6—H6 | 120.1 | C16—C17—O4 | 110.46 (15) |
O1—C7—N1 | 119.73 (13) | C16—C17—C18 | 130.66 (17) |
O1—C7—C8 | 132.19 (14) | O4—C17—C18 | 118.81 (14) |
N1—C7—C8 | 108.00 (13) | O3—C18—C8 | 118.90 (14) |
C7—C8—C9 | 103.90 (13) | O3—C18—C17 | 118.88 (14) |
C7—C8—C18 | 121.47 (14) | C8—C18—C17 | 122.20 (14) |
C9—C8—C18 | 134.62 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O3 | 0.82 | 2.23 | 2.8562 (16) | 133 |
O1—H1···O3i | 0.82 | 1.97 | 2.6979 (16) | 147 |
Symmetry code: (i) −x+2, −y+1, −z+1. |
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