Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803001399/ob6203sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803001399/ob6203Isup2.hkl |
CCDC reference: 204718
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.047
- wR factor = 0.148
- Data-to-parameter ratio = 15.4
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
To a stirred solution of 3-p-methylbenzylidene-4-flavanone (3 mmol) and N-(p-chlorobenzhydroxyiminoyl chloride (3 mmol) in dry CHCl3 (5 ml), 3.3 mmol of triethylamine was added. The reaction was monitored by TLC. After completion of the reaction, water was added to remove triethylamine hydrochloride and the resulting solution extracted with CHCl3. The extracts were combined and dried using MgSO4 and the product was purified by column chromatography (hexane/ethylacetate 9:1). The title compound, (I), was recrystallized from ethylacetate/hexane.
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: SDP (Frenz, 1978); 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: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: PARST97 (Nardelli, 1995) and PLATON (Spek, 1998).
Fig. 1. A view of the molecular structure of (I), showing ellipsoids at the 40% probability level for non-H atoms. |
C30H22ClNO3 | F(000) = 1000 |
Mr = 479.94 | Dx = 1.296 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.5418 Å |
a = 14.139 (2) Å | Cell parameters from 25 reflections |
b = 10.939 (2) Å | θ = 14–25° |
c = 16.139 (3) Å | µ = 1.63 mm−1 |
β = 99.809 (13)° | T = 293 K |
V = 2459.8 (8) Å3 | Needle, colourless |
Z = 4 | 0.18 × 0.17 × 0.10 mm |
Enraf-Nonius CAD-4 diffractometer | 2453 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.028 |
Graphite monochromator | θmax = 72.4°, θmin = 3.9° |
ω–2θ scans | h = 0→17 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→13 |
Tmin = 0.711, Tmax = 0.849 | l = −19→19 |
5076 measured reflections | 3 standard reflections every 200 reflections |
4874 independent reflections | intensity decay: <0.1% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.148 | w = 1/[σ2(Fo2) + (0.0767P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max < 0.001 |
4874 reflections | Δρmax = 0.30 e Å−3 |
317 parameters | Δρmin = −0.27 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00123 (18) |
C30H22ClNO3 | V = 2459.8 (8) Å3 |
Mr = 479.94 | Z = 4 |
Monoclinic, P21/n | Cu Kα radiation |
a = 14.139 (2) Å | µ = 1.63 mm−1 |
b = 10.939 (2) Å | T = 293 K |
c = 16.139 (3) Å | 0.18 × 0.17 × 0.10 mm |
β = 99.809 (13)° |
Enraf-Nonius CAD-4 diffractometer | 2453 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.028 |
Tmin = 0.711, Tmax = 0.849 | 3 standard reflections every 200 reflections |
5076 measured reflections | intensity decay: <0.1% |
4874 independent reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.148 | H-atom parameters constrained |
S = 0.98 | Δρmax = 0.30 e Å−3 |
4874 reflections | Δρmin = −0.27 e Å−3 |
317 parameters |
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 | 0.48394 (7) | 0.22331 (13) | 0.11159 (9) | 0.1291 (5) | |
O1 | 0.97704 (12) | 0.13999 (16) | −0.06583 (11) | 0.0485 (4) | |
N2 | 0.87833 (15) | 0.14080 (19) | −0.05983 (13) | 0.0485 (5) | |
C3 | 0.86503 (16) | 0.2111 (2) | 0.00077 (15) | 0.0418 (6) | |
C4 | 0.95543 (16) | 0.2687 (2) | 0.04871 (15) | 0.0394 (5) | |
H4 | 0.9480 | 0.3578 | 0.0491 | 0.047* | |
C5 | 1.02670 (16) | 0.2337 (2) | −0.00926 (14) | 0.0380 (5) | |
O1' | 1.17522 (12) | 0.13481 (16) | −0.03153 (11) | 0.0513 (5) | |
C2' | 1.12083 (17) | 0.1750 (2) | 0.03241 (15) | 0.0434 (6) | |
H2' | 1.1035 | 0.1010 | 0.0606 | 0.052* | |
C4' | 1.04242 (18) | 0.3332 (2) | −0.07147 (15) | 0.0441 (6) | |
C5' | 1.12448 (19) | 0.3144 (2) | −0.11481 (16) | 0.0475 (6) | |
C6' | 1.18628 (18) | 0.2167 (3) | −0.09311 (16) | 0.0485 (6) | |
O7' | 0.98721 (14) | 0.41935 (17) | −0.08601 (12) | 0.0621 (5) | |
C6 | 0.97565 (15) | 0.2215 (2) | 0.13861 (14) | 0.0389 (5) | |
C7 | 0.95756 (17) | 0.1020 (2) | 0.15689 (15) | 0.0447 (6) | |
H7 | 0.9316 | 0.0495 | 0.1136 | 0.054* | |
C8 | 0.97733 (19) | 0.0582 (3) | 0.23868 (16) | 0.0532 (7) | |
H8 | 0.9646 | −0.0231 | 0.2497 | 0.064* | |
C9 | 1.01606 (19) | 0.1351 (3) | 0.30439 (16) | 0.0557 (7) | |
C10 | 1.03466 (19) | 0.2546 (3) | 0.28580 (17) | 0.0574 (7) | |
H10 | 1.0613 | 0.3071 | 0.3289 | 0.069* | |
C11 | 1.01456 (17) | 0.2980 (3) | 0.20450 (16) | 0.0490 (6) | |
H11 | 1.0272 | 0.3793 | 0.1936 | 0.059* | |
C12 | 0.76942 (17) | 0.2185 (3) | 0.02463 (16) | 0.0482 (6) | |
C13 | 0.74637 (19) | 0.3115 (3) | 0.07519 (17) | 0.0596 (8) | |
H13 | 0.7909 | 0.3731 | 0.0920 | 0.072* | |
C14 | 0.6577 (2) | 0.3149 (3) | 0.1015 (2) | 0.0740 (9) | |
H14 | 0.6423 | 0.3787 | 0.1348 | 0.089* | |
C15 | 0.5936 (2) | 0.2231 (4) | 0.0775 (2) | 0.0761 (10) | |
C16 | 0.6147 (2) | 0.1305 (3) | 0.0273 (3) | 0.0830 (11) | |
H16 | 0.5700 | 0.0691 | 0.0110 | 0.100* | |
C17 | 0.7028 (2) | 0.1276 (3) | 0.0002 (2) | 0.0663 (8) | |
H17 | 0.7169 | 0.0645 | −0.0344 | 0.080* | |
C18 | 1.2625 (2) | 0.1971 (3) | −0.13522 (18) | 0.0651 (8) | |
H18 | 1.3039 | 0.1316 | −0.1204 | 0.078* | |
C19 | 1.2766 (2) | 0.2736 (4) | −0.1983 (2) | 0.0755 (9) | |
H19 | 1.3271 | 0.2591 | −0.2271 | 0.091* | |
C20 | 1.2169 (2) | 0.3731 (3) | −0.2203 (2) | 0.0763 (10) | |
H20 | 1.2284 | 0.4264 | −0.2623 | 0.092* | |
C21 | 1.1408 (2) | 0.3920 (3) | −0.17953 (17) | 0.0621 (8) | |
H21 | 1.0996 | 0.4573 | −0.1952 | 0.074* | |
C22 | 1.18460 (17) | 0.2495 (2) | 0.09834 (15) | 0.0431 (6) | |
C23 | 1.24024 (19) | 0.1861 (3) | 0.16340 (17) | 0.0601 (8) | |
H23 | 1.2373 | 0.1012 | 0.1648 | 0.072* | |
C24 | 1.3003 (2) | 0.2486 (4) | 0.22648 (19) | 0.0758 (10) | |
H24 | 1.3372 | 0.2055 | 0.2701 | 0.091* | |
C25 | 1.3053 (2) | 0.3729 (4) | 0.2243 (2) | 0.0768 (10) | |
H25 | 1.3455 | 0.4146 | 0.2667 | 0.092* | |
C26 | 1.2513 (2) | 0.4369 (3) | 0.1600 (2) | 0.0717 (9) | |
H26 | 1.2552 | 0.5217 | 0.1585 | 0.086* | |
C27 | 1.1908 (2) | 0.3751 (3) | 0.09715 (18) | 0.0558 (7) | |
H27 | 1.1540 | 0.4188 | 0.0538 | 0.067* | |
C28 | 1.0350 (3) | 0.0892 (4) | 0.39421 (18) | 0.0894 (11) | |
H28A | 1.0179 | 0.0043 | 0.3952 | 0.134* | |
H28B | 0.9973 | 0.1353 | 0.4273 | 0.134* | |
H28C | 1.1019 | 0.0988 | 0.4171 | 0.134* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0696 (6) | 0.1606 (12) | 0.1727 (12) | 0.0128 (7) | 0.0649 (7) | 0.0286 (9) |
O1 | 0.0499 (10) | 0.0450 (11) | 0.0518 (10) | −0.0016 (8) | 0.0121 (8) | −0.0134 (8) |
N2 | 0.0457 (12) | 0.0498 (14) | 0.0489 (13) | −0.0005 (11) | 0.0046 (10) | −0.0032 (10) |
C3 | 0.0441 (13) | 0.0410 (14) | 0.0399 (13) | 0.0024 (11) | 0.0055 (10) | −0.0016 (11) |
C4 | 0.0411 (12) | 0.0330 (13) | 0.0440 (13) | 0.0033 (10) | 0.0074 (10) | −0.0048 (11) |
C5 | 0.0417 (12) | 0.0327 (13) | 0.0398 (12) | −0.0001 (10) | 0.0072 (10) | −0.0059 (10) |
O1' | 0.0559 (11) | 0.0477 (11) | 0.0535 (11) | 0.0123 (9) | 0.0185 (9) | −0.0016 (9) |
C2' | 0.0451 (13) | 0.0428 (15) | 0.0440 (13) | 0.0054 (11) | 0.0128 (11) | −0.0016 (11) |
C4' | 0.0537 (14) | 0.0360 (14) | 0.0431 (14) | 0.0019 (12) | 0.0101 (11) | −0.0028 (11) |
C5' | 0.0561 (15) | 0.0454 (15) | 0.0433 (13) | −0.0018 (13) | 0.0151 (11) | −0.0025 (12) |
C6' | 0.0513 (14) | 0.0506 (16) | 0.0450 (14) | −0.0019 (13) | 0.0120 (11) | −0.0075 (13) |
O7' | 0.0758 (13) | 0.0509 (12) | 0.0629 (12) | 0.0205 (10) | 0.0215 (10) | 0.0121 (10) |
C6 | 0.0387 (12) | 0.0397 (13) | 0.0391 (12) | 0.0019 (11) | 0.0090 (9) | −0.0037 (11) |
C7 | 0.0473 (14) | 0.0418 (15) | 0.0445 (14) | 0.0002 (12) | 0.0068 (11) | −0.0073 (12) |
C8 | 0.0597 (16) | 0.0525 (17) | 0.0480 (15) | 0.0046 (13) | 0.0107 (12) | 0.0048 (13) |
C9 | 0.0549 (16) | 0.074 (2) | 0.0374 (14) | 0.0054 (15) | 0.0059 (12) | −0.0015 (14) |
C10 | 0.0592 (16) | 0.066 (2) | 0.0461 (16) | −0.0065 (15) | 0.0067 (13) | −0.0127 (14) |
C11 | 0.0494 (14) | 0.0512 (17) | 0.0466 (14) | −0.0077 (13) | 0.0087 (11) | −0.0103 (13) |
C12 | 0.0423 (13) | 0.0537 (17) | 0.0475 (14) | 0.0037 (12) | 0.0042 (11) | 0.0049 (13) |
C13 | 0.0499 (15) | 0.072 (2) | 0.0564 (17) | 0.0047 (15) | 0.0069 (13) | −0.0080 (16) |
C14 | 0.0614 (18) | 0.098 (3) | 0.066 (2) | 0.0167 (19) | 0.0213 (15) | −0.003 (2) |
C15 | 0.0538 (17) | 0.089 (3) | 0.090 (2) | 0.0118 (18) | 0.0270 (16) | 0.020 (2) |
C16 | 0.0504 (17) | 0.073 (2) | 0.125 (3) | −0.0076 (17) | 0.0145 (19) | 0.013 (2) |
C17 | 0.0484 (16) | 0.0600 (19) | 0.090 (2) | −0.0007 (15) | 0.0094 (15) | 0.0017 (17) |
C18 | 0.0560 (16) | 0.080 (2) | 0.0634 (18) | 0.0060 (16) | 0.0227 (14) | −0.0074 (17) |
C19 | 0.0661 (19) | 0.100 (3) | 0.067 (2) | −0.006 (2) | 0.0332 (16) | −0.009 (2) |
C20 | 0.090 (2) | 0.083 (3) | 0.063 (2) | −0.012 (2) | 0.0340 (18) | 0.0069 (18) |
C21 | 0.078 (2) | 0.0568 (19) | 0.0553 (17) | −0.0033 (16) | 0.0214 (15) | 0.0044 (15) |
C22 | 0.0404 (12) | 0.0449 (15) | 0.0456 (14) | 0.0024 (11) | 0.0120 (10) | −0.0001 (12) |
C23 | 0.0530 (16) | 0.071 (2) | 0.0549 (17) | 0.0058 (15) | 0.0053 (13) | 0.0110 (15) |
C24 | 0.0596 (19) | 0.109 (3) | 0.054 (2) | 0.0020 (19) | −0.0047 (15) | 0.0061 (19) |
C25 | 0.0560 (19) | 0.113 (3) | 0.059 (2) | −0.018 (2) | 0.0037 (16) | −0.019 (2) |
C26 | 0.070 (2) | 0.072 (2) | 0.071 (2) | −0.0204 (17) | 0.0086 (17) | −0.0184 (18) |
C27 | 0.0581 (16) | 0.0534 (18) | 0.0539 (16) | −0.0023 (14) | 0.0037 (13) | −0.0061 (14) |
C28 | 0.107 (3) | 0.112 (3) | 0.0469 (18) | 0.001 (2) | 0.0074 (18) | 0.0099 (19) |
Cl1—C15 | 1.732 (3) | C12—C13 | 1.377 (4) |
O1—N2 | 1.415 (2) | C12—C17 | 1.381 (4) |
O1—C5 | 1.469 (3) | C13—C14 | 1.391 (4) |
N2—C3 | 1.283 (3) | C13—H13 | 0.9300 |
C3—C12 | 1.470 (3) | C14—C15 | 1.363 (5) |
C3—C4 | 1.514 (3) | C14—H14 | 0.9300 |
C4—C6 | 1.520 (3) | C15—C16 | 1.361 (5) |
C4—C5 | 1.536 (3) | C16—C17 | 1.388 (4) |
C4—H4 | 0.9800 | C16—H16 | 0.9300 |
C5—C4' | 1.522 (3) | C17—H17 | 0.9300 |
C5—C2' | 1.527 (3) | C18—C19 | 1.359 (4) |
O1'—C6' | 1.366 (3) | C18—H18 | 0.9300 |
O1'—C2' | 1.456 (3) | C19—C20 | 1.385 (4) |
C2'—C22 | 1.511 (3) | C19—H19 | 0.9300 |
C2'—H2' | 0.9800 | C20—C21 | 1.369 (4) |
C4'—O7' | 1.221 (3) | C20—H20 | 0.9300 |
C4'—O7' | 1.221 (3) | C21—H21 | 0.9300 |
C4'—C5' | 1.468 (3) | C22—C27 | 1.377 (4) |
C5'—C6' | 1.387 (4) | C22—C23 | 1.386 (3) |
C5'—C21 | 1.396 (4) | C23—C24 | 1.389 (4) |
C6'—C18 | 1.385 (4) | C23—H23 | 0.9300 |
C6—C7 | 1.374 (3) | C24—C25 | 1.363 (5) |
C6—C11 | 1.391 (3) | C24—H24 | 0.9300 |
C7—C8 | 1.387 (3) | C25—C26 | 1.372 (4) |
C7—H7 | 0.9300 | C25—H25 | 0.9300 |
C8—C9 | 1.391 (4) | C26—C27 | 1.386 (4) |
C8—H8 | 0.9300 | C26—H26 | 0.9300 |
C9—C10 | 1.377 (4) | C27—H27 | 0.9300 |
C9—C28 | 1.514 (4) | C28—H28A | 0.9600 |
C10—C11 | 1.378 (4) | C28—H28B | 0.9600 |
C10—H10 | 0.9300 | C28—H28C | 0.9600 |
C11—H11 | 0.9300 | ||
N2—O1—C5 | 109.00 (16) | C13—C12—C3 | 121.1 (2) |
C3—N2—O1 | 109.28 (19) | C17—C12—C3 | 119.9 (3) |
N2—C3—C12 | 119.6 (2) | C12—C13—C14 | 121.1 (3) |
N2—C3—C4 | 114.7 (2) | C12—C13—H13 | 119.4 |
C12—C3—C4 | 125.3 (2) | C14—C13—H13 | 119.4 |
C3—C4—C6 | 110.6 (2) | C15—C14—C13 | 118.9 (3) |
C3—C4—C5 | 99.74 (18) | C15—C14—H14 | 120.5 |
C6—C4—C5 | 117.40 (19) | C13—C14—H14 | 120.5 |
C3—C4—H4 | 109.5 | C16—C15—C14 | 121.0 (3) |
C6—C4—H4 | 109.5 | C16—C15—Cl1 | 119.3 (3) |
C5—C4—H4 | 109.5 | C14—C15—Cl1 | 119.7 (3) |
O1—C5—C4' | 101.36 (18) | C15—C16—C17 | 120.3 (3) |
O1—C5—C2' | 105.59 (18) | C15—C16—H16 | 119.9 |
C4'—C5—C2' | 112.2 (2) | C17—C16—H16 | 119.9 |
O1—C5—C4 | 105.00 (17) | C12—C17—C16 | 119.9 (3) |
C4'—C5—C4 | 114.07 (19) | C12—C17—H17 | 120.1 |
C2'—C5—C4 | 116.73 (19) | C16—C17—H17 | 120.1 |
C6'—O1'—C2' | 117.21 (19) | C19—C18—C6' | 119.9 (3) |
O1'—C2'—C22 | 109.76 (19) | C19—C18—H18 | 120.1 |
O1'—C2'—C5 | 109.92 (19) | C6'—C18—H18 | 120.1 |
C22—C2'—C5 | 117.0 (2) | C18—C19—C20 | 121.0 (3) |
O1'—C2'—H2' | 106.5 | C18—C19—H19 | 119.5 |
C22—C2'—H2' | 106.5 | C20—C19—H19 | 119.5 |
C5—C2'—H2' | 106.5 | C21—C20—C19 | 119.3 (3) |
O7'—C4'—C5' | 123.2 (2) | C21—C20—H20 | 120.3 |
O7'—C4'—C5' | 123.2 (2) | C19—C20—H20 | 120.3 |
O7'—C4'—C5 | 121.2 (2) | C20—C21—C5' | 120.8 (3) |
O7'—C4'—C5 | 121.2 (2) | C20—C21—H21 | 119.6 |
C5'—C4'—C5 | 115.5 (2) | C5'—C21—H21 | 119.6 |
C6'—C5'—C21 | 118.7 (2) | C27—C22—C23 | 118.7 (3) |
C6'—C5'—C4' | 120.2 (2) | C27—C22—C2' | 124.1 (2) |
C21—C5'—C4' | 121.1 (3) | C23—C22—C2' | 117.2 (2) |
O1'—C6'—C18 | 116.8 (2) | C22—C23—C24 | 120.4 (3) |
O1'—C6'—C5' | 122.9 (2) | C22—C23—H23 | 119.8 |
C18—C6'—C5' | 120.3 (3) | C24—C23—H23 | 119.8 |
C7—C6—C11 | 118.2 (2) | C25—C24—C23 | 120.0 (3) |
C7—C6—C4 | 121.1 (2) | C25—C24—H24 | 120.0 |
C11—C6—C4 | 120.7 (2) | C23—C24—H24 | 120.0 |
C6—C7—C8 | 121.2 (2) | C24—C25—C26 | 120.3 (3) |
C6—C7—H7 | 119.4 | C24—C25—H25 | 119.9 |
C8—C7—H7 | 119.4 | C26—C25—H25 | 119.9 |
C7—C8—C9 | 120.4 (3) | C25—C26—C27 | 120.0 (3) |
C7—C8—H8 | 119.8 | C25—C26—H26 | 120.0 |
C9—C8—H8 | 119.8 | C27—C26—H26 | 120.0 |
C10—C9—C8 | 118.2 (2) | C22—C27—C26 | 120.6 (3) |
C10—C9—C28 | 121.0 (3) | C22—C27—H27 | 119.7 |
C8—C9—C28 | 120.8 (3) | C26—C27—H27 | 119.7 |
C11—C10—C9 | 121.2 (3) | C9—C28—H28A | 109.5 |
C11—C10—H10 | 119.4 | C9—C28—H28B | 109.5 |
C9—C10—H10 | 119.4 | H28A—C28—H28B | 109.5 |
C10—C11—C6 | 120.8 (3) | C9—C28—H28C | 109.5 |
C10—C11—H11 | 119.6 | H28A—C28—H28C | 109.5 |
C6—C11—H11 | 119.6 | H28B—C28—H28C | 109.5 |
C13—C12—C17 | 118.8 (3) | ||
C5—O1—N2—C3 | −8.5 (3) | C3—C4—C6—C7 | 37.1 (3) |
O1—N2—C3—C12 | −174.5 (2) | C5—C4—C6—C7 | −76.4 (3) |
O1—N2—C3—C4 | −1.6 (3) | C3—C4—C6—C11 | −144.0 (2) |
N2—C3—C4—C6 | −114.2 (2) | C5—C4—C6—C11 | 102.5 (3) |
C12—C3—C4—C6 | 58.2 (3) | C11—C6—C7—C8 | 0.1 (4) |
N2—C3—C4—C5 | 10.1 (3) | C4—C6—C7—C8 | 179.0 (2) |
C12—C3—C4—C5 | −177.5 (2) | C6—C7—C8—C9 | 0.1 (4) |
N2—O1—C5—C4' | −104.55 (19) | C7—C8—C9—C10 | −0.5 (4) |
N2—O1—C5—C2' | 138.36 (19) | C7—C8—C9—C28 | 178.1 (3) |
N2—O1—C5—C4 | 14.4 (2) | C8—C9—C10—C11 | 0.8 (4) |
C3—C4—C5—O1 | −13.9 (2) | C28—C9—C10—C11 | −177.8 (3) |
C6—C4—C5—O1 | 105.5 (2) | C9—C10—C11—C6 | −0.6 (4) |
C3—C4—C5—C4' | 96.2 (2) | C7—C6—C11—C10 | 0.2 (4) |
C6—C4—C5—C4' | −144.4 (2) | C4—C6—C11—C10 | −178.7 (2) |
C3—C4—C5—C2' | −130.4 (2) | N2—C3—C12—C13 | −165.1 (3) |
C6—C4—C5—C2' | −11.0 (3) | C4—C3—C12—C13 | 22.8 (4) |
C6'—O1'—C2'—C22 | −81.4 (3) | N2—C3—C12—C17 | 18.6 (4) |
C6'—O1'—C2'—C5 | 48.6 (3) | C4—C3—C12—C17 | −153.5 (3) |
O1—C5—C2'—O1' | 57.4 (2) | C17—C12—C13—C14 | −0.1 (4) |
C4'—C5—C2'—O1' | −52.2 (3) | C3—C12—C13—C14 | −176.5 (3) |
C4—C5—C2'—O1' | 173.57 (19) | C12—C13—C14—C15 | 1.1 (5) |
O1—C5—C2'—C22 | −176.59 (19) | C13—C14—C15—C16 | −1.3 (5) |
C4'—C5—C2'—C22 | 73.9 (3) | C13—C14—C15—Cl1 | 178.4 (2) |
C4—C5—C2'—C22 | −60.4 (3) | C14—C15—C16—C17 | 0.7 (6) |
O1—C5—C4'—O7' | 96.5 (3) | Cl1—C15—C16—C17 | −179.1 (3) |
C2'—C5—C4'—O7' | −151.3 (2) | C13—C12—C17—C16 | −0.6 (4) |
C4—C5—C4'—O7' | −15.8 (3) | C3—C12—C17—C16 | 175.9 (3) |
O1—C5—C4'—O7' | 96.5 (3) | C15—C16—C17—C12 | 0.3 (5) |
C2'—C5—C4'—O7' | −151.3 (2) | O1'—C6'—C18—C19 | 178.7 (3) |
C4—C5—C4'—O7' | −15.8 (3) | C5'—C6'—C18—C19 | −0.2 (4) |
O1—C5—C4'—C5' | −80.5 (2) | C6'—C18—C19—C20 | 1.3 (5) |
C2'—C5—C4'—C5' | 31.7 (3) | C18—C19—C20—C21 | −2.1 (5) |
C4—C5—C4'—C5' | 167.2 (2) | C19—C20—C21—C5' | 1.8 (5) |
O7'—C4'—C5'—C6' | 177.8 (2) | C6'—C5'—C21—C20 | −0.7 (4) |
O7'—C4'—C5'—C6' | 177.8 (2) | C4'—C5'—C21—C20 | −179.3 (3) |
C5—C4'—C5'—C6' | −5.3 (3) | O1'—C2'—C22—C27 | 94.4 (3) |
O7'—C4'—C5'—C21 | −3.7 (4) | C5—C2'—C22—C27 | −31.8 (3) |
O7'—C4'—C5'—C21 | −3.7 (4) | O1'—C2'—C22—C23 | −85.3 (3) |
C5—C4'—C5'—C21 | 173.3 (2) | C5—C2'—C22—C23 | 148.6 (2) |
C2'—O1'—C6'—C18 | 158.3 (2) | C27—C22—C23—C24 | 0.6 (4) |
C2'—O1'—C6'—C5' | −22.8 (3) | C2'—C22—C23—C24 | −179.8 (2) |
C21—C5'—C6'—O1' | −179.0 (2) | C22—C23—C24—C25 | −0.4 (5) |
C4'—C5'—C6'—O1' | −0.4 (4) | C23—C24—C25—C26 | −0.1 (5) |
C21—C5'—C6'—C18 | −0.1 (4) | C24—C25—C26—C27 | 0.5 (5) |
C4'—C5'—C6'—C18 | 178.5 (2) | C23—C22—C27—C26 | −0.2 (4) |
C5'—C4'—O7'—O7' | 0 (87) | C2'—C22—C27—C26 | −179.9 (2) |
C5—C4'—O7'—O7' | 0 (91) | C25—C26—C27—C22 | −0.3 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O7′ | 0.98 | 2.43 | 2.824 (3) | 103 |
C7—H7···O1′i | 0.93 | 2.72 | 3.610 (3) | 160 |
C2′—H2′···N2i | 0.98 | 2.66 | 3.482 (3) | 142 |
C4—H4···O7′ii | 0.98 | 2.64 | 3.535 (3) | 153 |
C19—H19···Cg(1)iii | 0.93 | 2.75 | 3.597 | 153 |
Symmetry codes: (i) −x+2, −y, −z; (ii) −x+2, −y+1, −z; (iii) x−1/2, −y−1/2, z−3/2. |
Experimental details
Crystal data | |
Chemical formula | C30H22ClNO3 |
Mr | 479.94 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 14.139 (2), 10.939 (2), 16.139 (3) |
β (°) | 99.809 (13) |
V (Å3) | 2459.8 (8) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 1.63 |
Crystal size (mm) | 0.18 × 0.17 × 0.10 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.711, 0.849 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5076, 4874, 2453 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.618 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.148, 0.98 |
No. of reflections | 4874 |
No. of parameters | 317 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.27 |
Computer programs: CAD-4 Software (Enraf-Nonius, 1989), SDP (Frenz, 1978), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolnai, 1997), PARST97 (Nardelli, 1995) and PLATON (Spek, 1998).
O1—N2 | 1.415 (2) | O1'—C6' | 1.366 (3) |
O1—C5 | 1.469 (3) | O1'—C2' | 1.456 (3) |
N2—C3 | 1.283 (3) | C4'—O7' | 1.221 (3) |
C3—C4 | 1.514 (3) | C4'—C5' | 1.468 (3) |
C5—C4' | 1.522 (3) | C5'—C6' | 1.387 (4) |
C5—C2' | 1.527 (3) | C8—C9 | 1.391 (4) |
C5—O1—N2—C3 | −8.5 (3) | N2—O1—C5—C4 | 14.4 (2) |
O1—N2—C3—C4 | −1.6 (3) | C3—C4—C5—O1 | −13.9 (2) |
N2—C3—C4—C5 | 10.1 (3) | C5—C2'—C22—C23 | 148.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O7' | 0.98 | 2.43 | 2.824 (3) | 103 |
C7—H7···O1'i | 0.93 | 2.72 | 3.610 (3) | 160 |
C2'—H2'···N2i | 0.98 | 2.66 | 3.482 (3) | 142 |
C4—H4···O7'ii | 0.98 | 2.64 | 3.535 (3) | 153 |
C19—H19···Cg(1)iii | 0.93 | 2.75 | 3.597 | 153 |
Symmetry codes: (i) −x+2, −y, −z; (ii) −x+2, −y+1, −z; (iii) x−1/2, −y−1/2, z−3/2. |
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Flavonones are widely distributed and they form a part of our human diet, owing to their abundance in edible plants. The different properties and activities possessed by these compounds are discussed in our previous article (Jeyabharathi et al., 2003). To understand the structure and conformation, a crystallographic study of the title compound, (I), was undertaken.
The bond geometry of the flavanone moiety in (I) agrees with reported values (Tomlin & Cantrell, 1990). As shown in Fig. 1, the pyran ring is planar, with the fused phenyl ring making the dihedral angle of 3.9 (1)°, which is larger than the reported value (Kendi & Ozbey, 1995). This may be due to the substitution at C5. The best plane of the benzopyran ring is perpendicular to the isozazoline ring plane. A study of torsion angles and asymmetry parameters (Cremer & Pople, 1975) reveals that the pyran ring adopts a slightly distorted sofa conformation [q2 = 0.343 (2) Å, q3 = −0.263 (2) Å, QT = 0.432 (2) Å and ϕ2 = −107.3 (4)°]. For the isoxazoline ring, q2 = 0.146 (2) Å and ϕ2 = −41.3 (9)°, which confirm its conformation. Apart from van der Waals interactions, the packing of the molecules in the crystal lattice is stabilized by intermolecular C—H···O, C—H···N and C—H···π interactions. Then C19—H19 proton points along the π bond of the C22—C27(x − 1/2, −1/2 − y, z − 3/2) phenyl ring, suggesting a C—H···π intermolecular interaction (Table 2). The geometry of these interactions is comparable with the literature (Abdul Ajees et al., 2001; Gallagher et al., 2000; Kooijman et al., 2000).