Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027601/hg6234sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027601/hg6234Isup2.hkl |
CCDC reference: 287592
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.007 Å
- R factor = 0.051
- wR factor = 0.150
- Data-to-parameter ratio = 9.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT731_ALERT_1_C Bond Calc 0.85(5), Rep 0.851(19) ...... 2.63 su-Rat N1 -H1X 1.555 1.555
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.48 From the CIF: _reflns_number_total 2171 Count of symmetry unique reflns 2197 Completeness (_total/calc) 98.82% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion
10-(3-Aminobenzylidene)anthrone was prepared according to the literature method of Ingram (1950). A mixture of 10-(3-aminobenzylidene)anthrone (0.6 g), acetic anhydride (20 ml) and pyridine (0.5 ml) was added to a 100 ml flask and then stirred. The reaction was continued for 1.5 h at room temperature, followed by filtration and washing with alcohol [Ethanol?]. The collected crude product was recrystallized with alcohol [Ethanol?] to afford yellow crystals of (I) (0.4 g, yield 59.0%, m.p. 462–465 K). Spectroscopic analysis: IR (KBr, ν, cm−1): 3319, 1687, 1645, 1602, 1544, 1483, 1417, 1372, 1319, 1277, 932, 776, 683; 1H NMR (CDCl3, δ, p.p.m.): 7.52 (s, 1H, C═CH), 7.00–8.28 (m, 12H), 2.18 (s, 3H, –CH3). MS (%): 340 (M+1, 10), 339 (M, 22), 297 (11), 296 (32), 281 (17), 280 (47), 239 (10), 43 (100).
H atoms were positioned geometrically, with C—H distances set to 0.96 Å for methyl H atoms and 0.93 Å for the remainder, and refined using the riding-model approximation, with Uiso(H) = 1.2 (or 1.5 for methyl H atoms) times Ueq(parent atom). Due to the absence of any significant anomalous scatterers in the molecule, attempts to determine the absolute structure by refinement of the Flack parameter were inconclusive. Therefore, the Friedel pairs were merged before the final refinement and the absolute configuration remained undetermined.
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD (McArdle, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C23H17NO2 | F(000) = 356 |
Mr = 339.38 | Dx = 1.264 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 25 reflections |
a = 12.3847 (3) Å | θ = 3.3–27.5° |
b = 7.4853 (4) Å | µ = 0.08 mm−1 |
c = 12.3351 (3) Å | T = 296 K |
β = 128.764 (4)° | Block, yellow |
V = 891.63 (8) Å3 | 0.34 × 0.23 × 0.14 mm |
Z = 2 |
Enraf–Nonius CAD-4 diffractometer | 1626 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.029 |
Graphite monochromator | θmax = 27.5°, θmin = 1.8° |
ω–2θ scans | h = −16→0 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −9→9 |
Tmin = 0.963, Tmax = 0.989 | l = −11→16 |
3717 measured reflections | 3 standard reflections every 60 min |
2171 independent reflections | intensity decay: none |
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)] = 0.051 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.151 | w = 1/[σ2(Fo2) + (0.0888P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
2171 reflections | Δρmax = 0.34 e Å−3 |
241 parameters | Δρmin = −0.33 e Å−3 |
2 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.084 (12) |
C23H17NO2 | V = 891.63 (8) Å3 |
Mr = 339.38 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 12.3847 (3) Å | µ = 0.08 mm−1 |
b = 7.4853 (4) Å | T = 296 K |
c = 12.3351 (3) Å | 0.34 × 0.23 × 0.14 mm |
β = 128.764 (4)° |
Enraf–Nonius CAD-4 diffractometer | 1626 reflections with I > 2σ(I) |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | Rint = 0.029 |
Tmin = 0.963, Tmax = 0.989 | 3 standard reflections every 60 min |
3717 measured reflections | intensity decay: none |
2171 independent reflections |
R[F2 > 2σ(F2)] = 0.051 | 2 restraints |
wR(F2) = 0.151 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | Δρmax = 0.34 e Å−3 |
2171 reflections | Δρmin = −0.33 e Å−3 |
241 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 | ||
O1 | 0.2202 (3) | 0.0772 (4) | 0.0075 (3) | 0.0740 (9) | |
O2 | −0.3858 (4) | −0.4173 (6) | 0.2636 (3) | 0.0986 (13) | |
N1 | −0.2766 (3) | −0.3305 (4) | 0.1791 (3) | 0.0501 (8) | |
H1X | −0.260 (4) | −0.360 (6) | 0.124 (3) | 0.061 (11)* | |
C1 | 0.3602 (4) | 0.2565 (5) | 0.4502 (4) | 0.0503 (9) | |
H1 | 0.3402 | 0.2682 | 0.5112 | 0.060* | |
C2 | 0.4885 (4) | 0.3066 (6) | 0.4935 (5) | 0.0588 (9) | |
H2 | 0.5531 | 0.3544 | 0.5819 | 0.071* | |
C3 | 0.5221 (4) | 0.2866 (6) | 0.4065 (5) | 0.0638 (11) | |
H3 | 0.6092 | 0.3197 | 0.4361 | 0.077* | |
C4 | 0.4259 (4) | 0.2174 (5) | 0.2763 (5) | 0.0621 (11) | |
H4 | 0.4491 | 0.2019 | 0.2183 | 0.074* | |
C5 | 0.1877 (4) | 0.1102 (5) | 0.0815 (3) | 0.0498 (8) | |
C6 | −0.0636 (5) | 0.0918 (5) | −0.1210 (4) | 0.0603 (10) | |
H6 | −0.0391 | 0.0718 | −0.1775 | 0.072* | |
C7 | −0.2007 (5) | 0.1065 (6) | −0.1798 (4) | 0.0687 (12) | |
H7 | −0.2689 | 0.0936 | −0.2753 | 0.082* | |
C8 | −0.2367 (4) | 0.1404 (6) | −0.0967 (4) | 0.0649 (11) | |
H8 | −0.3293 | 0.1563 | −0.1368 | 0.078* | |
C9 | −0.1352 (4) | 0.1513 (5) | 0.0476 (4) | 0.0540 (9) | |
H9 | −0.1614 | 0.1730 | 0.1025 | 0.065* | |
C10 | 0.1171 (3) | 0.1381 (4) | 0.2657 (3) | 0.0389 (7) | |
C11 | 0.2932 (4) | 0.1693 (5) | 0.2284 (4) | 0.0457 (8) | |
C12 | 0.0407 (3) | 0.1067 (5) | 0.0240 (3) | 0.0464 (8) | |
C13 | 0.0054 (3) | 0.1301 (4) | 0.1109 (3) | 0.0427 (7) | |
C14 | 0.2581 (3) | 0.1878 (4) | 0.3160 (3) | 0.0412 (7) | |
C15 | 0.0992 (3) | 0.1016 (5) | 0.3607 (3) | 0.0468 (8) | |
H15 | 0.1774 | 0.1180 | 0.4527 | 0.056* | |
C16 | −0.0253 (3) | 0.0395 (5) | 0.3415 (3) | 0.0451 (8) | |
C17 | −0.0967 (3) | −0.1142 (5) | 0.2677 (3) | 0.0437 (8) | |
H17 | −0.0681 | −0.1790 | 0.2254 | 0.052* | |
C18 | −0.2103 (3) | −0.1732 (5) | 0.2557 (3) | 0.0431 (8) | |
C19 | −0.2545 (4) | −0.0742 (6) | 0.3165 (4) | 0.0539 (9) | |
H19 | −0.3325 | −0.1093 | 0.3062 | 0.065* | |
C20 | −0.1818 (4) | 0.0769 (7) | 0.3924 (4) | 0.0642 (11) | |
H20 | −0.2102 | 0.1410 | 0.4352 | 0.077* | |
C21 | −0.0677 (4) | 0.1347 (6) | 0.4060 (4) | 0.0587 (10) | |
H21 | −0.0198 | 0.2364 | 0.4577 | 0.070* | |
C22 | −0.3596 (4) | −0.4412 (6) | 0.1845 (4) | 0.0599 (10) | |
C23 | −0.4162 (5) | −0.5972 (7) | 0.0868 (5) | 0.0760 (14) | |
H23A | −0.3740 | −0.7054 | 0.1389 | 0.114* | |
H23B | −0.3962 | −0.5823 | 0.0236 | 0.114* | |
H23C | −0.5146 | −0.6039 | 0.0352 | 0.114* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.111 (2) | 0.076 (2) | 0.0782 (16) | 0.0024 (19) | 0.0803 (17) | 0.0004 (17) |
O2 | 0.123 (3) | 0.122 (3) | 0.108 (2) | −0.059 (3) | 0.099 (2) | −0.036 (2) |
N1 | 0.0512 (17) | 0.0622 (19) | 0.0494 (15) | −0.0110 (14) | 0.0375 (14) | −0.0035 (15) |
C1 | 0.045 (2) | 0.058 (2) | 0.0510 (19) | −0.0033 (17) | 0.0319 (17) | −0.0025 (17) |
C2 | 0.046 (2) | 0.059 (2) | 0.0622 (19) | −0.0072 (18) | 0.0289 (17) | −0.004 (2) |
C3 | 0.046 (2) | 0.065 (3) | 0.087 (3) | −0.006 (2) | 0.045 (2) | 0.003 (2) |
C4 | 0.072 (3) | 0.059 (2) | 0.091 (3) | 0.002 (2) | 0.068 (3) | 0.006 (2) |
C5 | 0.071 (2) | 0.0409 (17) | 0.0560 (17) | 0.0019 (18) | 0.0488 (18) | 0.0057 (17) |
C6 | 0.084 (3) | 0.046 (2) | 0.0460 (17) | −0.006 (2) | 0.039 (2) | −0.0020 (17) |
C7 | 0.077 (3) | 0.050 (2) | 0.0424 (17) | −0.008 (2) | 0.0198 (18) | −0.0022 (18) |
C8 | 0.052 (2) | 0.055 (2) | 0.056 (2) | −0.0034 (19) | 0.0186 (18) | 0.005 (2) |
C9 | 0.048 (2) | 0.053 (2) | 0.0540 (18) | −0.0023 (17) | 0.0288 (16) | 0.0039 (18) |
C10 | 0.0387 (16) | 0.0416 (17) | 0.0428 (15) | −0.0004 (14) | 0.0287 (13) | −0.0006 (14) |
C11 | 0.054 (2) | 0.0410 (18) | 0.0579 (18) | 0.0008 (15) | 0.0428 (17) | 0.0041 (16) |
C12 | 0.062 (2) | 0.0358 (16) | 0.0431 (16) | −0.0030 (16) | 0.0340 (16) | 0.0000 (15) |
C13 | 0.0483 (18) | 0.0363 (17) | 0.0435 (15) | −0.0050 (15) | 0.0288 (15) | −0.0006 (15) |
C14 | 0.0427 (18) | 0.0402 (16) | 0.0465 (16) | −0.0001 (15) | 0.0308 (15) | 0.0018 (15) |
C15 | 0.0424 (17) | 0.060 (2) | 0.0421 (15) | −0.0084 (17) | 0.0284 (14) | −0.0051 (16) |
C16 | 0.0406 (17) | 0.061 (2) | 0.0387 (14) | −0.0048 (16) | 0.0272 (14) | −0.0007 (16) |
C17 | 0.0471 (19) | 0.054 (2) | 0.0434 (15) | −0.0024 (15) | 0.0348 (15) | −0.0013 (15) |
C18 | 0.0373 (17) | 0.060 (2) | 0.0357 (14) | −0.0018 (16) | 0.0247 (13) | 0.0037 (16) |
C19 | 0.046 (2) | 0.077 (3) | 0.0544 (19) | −0.002 (2) | 0.0386 (17) | 0.000 (2) |
C20 | 0.063 (2) | 0.085 (3) | 0.069 (2) | −0.004 (2) | 0.053 (2) | −0.015 (2) |
C21 | 0.058 (2) | 0.074 (3) | 0.0572 (19) | −0.013 (2) | 0.0428 (18) | −0.018 (2) |
C22 | 0.054 (2) | 0.074 (3) | 0.0532 (19) | −0.017 (2) | 0.0340 (18) | −0.002 (2) |
C23 | 0.075 (3) | 0.082 (3) | 0.074 (3) | −0.027 (3) | 0.048 (2) | −0.007 (3) |
O1—C5 | 1.231 (4) | C9—C13 | 1.401 (5) |
O2—C22 | 1.219 (4) | C9—H9 | 0.9300 |
N1—C22 | 1.354 (4) | C10—C15 | 1.350 (4) |
N1—C18 | 1.408 (5) | C10—C14 | 1.489 (4) |
N1—H1X | 0.851 (19) | C10—C13 | 1.502 (4) |
C1—C2 | 1.375 (5) | C11—C14 | 1.401 (4) |
C1—C14 | 1.408 (5) | C12—C13 | 1.399 (4) |
C1—H1 | 0.9300 | C15—C16 | 1.480 (4) |
C2—C3 | 1.381 (6) | C15—H15 | 0.9300 |
C2—H2 | 0.9300 | C16—C17 | 1.388 (5) |
C3—C4 | 1.368 (6) | C16—C21 | 1.393 (5) |
C3—H3 | 0.9300 | C17—C18 | 1.391 (4) |
C4—C11 | 1.401 (5) | C17—H17 | 0.9300 |
C4—H4 | 0.9300 | C18—C19 | 1.387 (5) |
C5—C12 | 1.484 (5) | C19—C20 | 1.383 (6) |
C5—C11 | 1.491 (5) | C19—H19 | 0.9300 |
C6—C7 | 1.371 (6) | C20—C21 | 1.384 (5) |
C6—C12 | 1.410 (5) | C20—H20 | 0.9300 |
C6—H6 | 0.9300 | C21—H21 | 0.9300 |
C7—C8 | 1.373 (6) | C22—C23 | 1.500 (6) |
C7—H7 | 0.9300 | C23—H23A | 0.9599 |
C8—C9 | 1.397 (5) | C23—H23B | 0.9599 |
C8—H8 | 0.9300 | C23—H23C | 0.9599 |
C22—N1—C18 | 128.4 (3) | C6—C12—C5 | 118.9 (3) |
C22—N1—H1X | 117 (3) | C12—C13—C9 | 117.5 (3) |
C18—N1—H1X | 115 (3) | C12—C13—C10 | 119.9 (3) |
C2—C1—C14 | 121.6 (3) | C9—C13—C10 | 122.5 (3) |
C2—C1—H1 | 119.2 | C11—C14—C1 | 117.3 (3) |
C14—C1—H1 | 119.2 | C11—C14—C10 | 120.2 (3) |
C1—C2—C3 | 120.5 (4) | C1—C14—C10 | 122.4 (3) |
C1—C2—H2 | 119.8 | C10—C15—C16 | 130.2 (3) |
C3—C2—H2 | 119.8 | C10—C15—H15 | 114.9 |
C4—C3—C2 | 119.2 (4) | C16—C15—H15 | 114.9 |
C4—C3—H3 | 120.4 | C17—C16—C21 | 119.0 (3) |
C2—C3—H3 | 120.4 | C17—C16—C15 | 122.5 (3) |
C3—C4—C11 | 121.5 (3) | C21—C16—C15 | 118.4 (3) |
C3—C4—H4 | 119.3 | C16—C17—C18 | 121.3 (3) |
C11—C4—H4 | 119.3 | C16—C17—H17 | 119.3 |
O1—C5—C12 | 121.0 (3) | C18—C17—H17 | 119.3 |
O1—C5—C11 | 121.1 (3) | C19—C18—C17 | 119.2 (3) |
C12—C5—C11 | 117.8 (3) | C19—C18—N1 | 123.2 (3) |
C7—C6—C12 | 120.7 (4) | C17—C18—N1 | 117.6 (3) |
C7—C6—H6 | 119.6 | C20—C19—C18 | 119.6 (3) |
C12—C6—H6 | 119.6 | C20—C19—H19 | 120.2 |
C6—C7—C8 | 119.6 (3) | C18—C19—H19 | 120.2 |
C6—C7—H7 | 120.2 | C19—C20—C21 | 121.3 (3) |
C8—C7—H7 | 120.2 | C19—C20—H20 | 119.3 |
C7—C8—C9 | 120.5 (4) | C21—C20—H20 | 119.3 |
C7—C8—H8 | 119.7 | C20—C21—C16 | 119.5 (4) |
C9—C8—H8 | 119.7 | C20—C21—H21 | 120.2 |
C8—C9—C13 | 121.1 (4) | C16—C21—H21 | 120.2 |
C8—C9—H9 | 119.5 | O2—C22—N1 | 122.7 (4) |
C13—C9—H9 | 119.5 | O2—C22—C23 | 122.2 (3) |
C15—C10—C14 | 118.5 (3) | N1—C22—C23 | 115.1 (3) |
C15—C10—C13 | 125.0 (3) | C22—C23—H23A | 109.5 |
C14—C10—C13 | 116.5 (2) | C22—C23—H23B | 109.5 |
C4—C11—C14 | 119.8 (3) | H23A—C23—H23B | 109.5 |
C4—C11—C5 | 119.5 (3) | C22—C23—H23C | 109.5 |
C14—C11—C5 | 120.5 (3) | H23A—C23—H23C | 109.5 |
C13—C12—C6 | 120.3 (3) | H23B—C23—H23C | 109.5 |
C13—C12—C5 | 120.7 (3) | ||
C14—C1—C2—C3 | −1.6 (6) | C4—C11—C14—C1 | 0.4 (5) |
C1—C2—C3—C4 | 0.5 (7) | C5—C11—C14—C1 | −175.5 (3) |
C2—C3—C4—C11 | 1.1 (6) | C4—C11—C14—C10 | 179.6 (3) |
C12—C6—C7—C8 | 1.6 (6) | C5—C11—C14—C10 | 3.7 (5) |
C6—C7—C8—C9 | −3.2 (6) | C2—C1—C14—C11 | 1.1 (5) |
C7—C8—C9—C13 | 0.7 (6) | C2—C1—C14—C10 | −178.0 (4) |
C3—C4—C11—C14 | −1.6 (6) | C15—C10—C14—C11 | 158.8 (3) |
C3—C4—C11—C5 | 174.4 (4) | C13—C10—C14—C11 | −20.3 (5) |
O1—C5—C11—C4 | 11.0 (5) | C15—C10—C14—C1 | −22.1 (5) |
C12—C5—C11—C4 | −164.2 (3) | C13—C10—C14—C1 | 158.9 (3) |
O1—C5—C11—C14 | −173.1 (4) | C14—C10—C15—C16 | −176.1 (4) |
C12—C5—C11—C14 | 11.8 (5) | C13—C10—C15—C16 | 2.9 (6) |
C7—C6—C12—C13 | 2.4 (5) | C10—C15—C16—C17 | 55.5 (6) |
C7—C6—C12—C5 | −173.2 (4) | C10—C15—C16—C21 | −127.7 (4) |
O1—C5—C12—C13 | 174.8 (3) | C21—C16—C17—C18 | 0.8 (5) |
C11—C5—C12—C13 | −10.0 (5) | C15—C16—C17—C18 | 177.5 (3) |
O1—C5—C12—C6 | −9.6 (5) | C16—C17—C18—C19 | 1.3 (5) |
C11—C5—C12—C6 | 165.6 (3) | C16—C17—C18—N1 | −179.9 (3) |
C6—C12—C13—C9 | −4.7 (5) | C22—N1—C18—C19 | −22.1 (6) |
C5—C12—C13—C9 | 170.9 (3) | C22—N1—C18—C17 | 159.2 (4) |
C6—C12—C13—C10 | 177.5 (3) | C17—C18—C19—C20 | −2.6 (5) |
C5—C12—C13—C10 | −7.0 (4) | N1—C18—C19—C20 | 178.7 (3) |
C8—C9—C13—C12 | 3.2 (5) | C18—C19—C20—C21 | 1.8 (6) |
C8—C9—C13—C10 | −179.1 (3) | C19—C20—C21—C16 | 0.3 (6) |
C15—C10—C13—C12 | −157.0 (3) | C17—C16—C21—C20 | −1.5 (6) |
C14—C10—C13—C12 | 22.0 (4) | C15—C16—C21—C20 | −178.5 (3) |
C15—C10—C13—C9 | 25.3 (5) | C18—N1—C22—O2 | −1.6 (7) |
C14—C10—C13—C9 | −155.7 (3) | C18—N1—C22—C23 | 179.1 (4) |
Experimental details
Crystal data | |
Chemical formula | C23H17NO2 |
Mr | 339.38 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 296 |
a, b, c (Å) | 12.3847 (3), 7.4853 (4), 12.3351 (3) |
β (°) | 128.764 (4) |
V (Å3) | 891.63 (8) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.34 × 0.23 × 0.14 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.963, 0.989 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3717, 2171, 1626 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.151, 1.10 |
No. of reflections | 2171 |
No. of parameters | 241 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.34, −0.33 |
Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), CAD-4 EXPRESS, XCAD (McArdle, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.
O1—C5 | 1.231 (4) | N1—C18 | 1.408 (5) |
O2—C22 | 1.219 (4) | C10—C15 | 1.350 (4) |
N1—C22 | 1.354 (4) | ||
C15—C10—C14 | 118.5 (3) | C17—C16—C21 | 119.0 (3) |
C15—C10—C13 | 125.0 (3) | C17—C16—C15 | 122.5 (3) |
C14—C10—C15—C16 | −176.1 (4) | C10—C15—C16—C21 | −127.7 (4) |
C13—C10—C15—C16 | 2.9 (6) | C22—N1—C18—C19 | −22.1 (6) |
C10—C15—C16—C17 | 55.5 (6) | C22—N1—C18—C17 | 159.2 (4) |
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It was reported recently that some 10-substituted benzylideneanthrones possess high antitumour activity (Paull et al., 1992). In our laboratory, some 10-substituted benzylideneanthrones have been prepared and evaluated for antitumour activity. Our study of the structure–activity relationship (SAR) showed that substitution in the phenyl moiety of the molecule affects its antitumour activity (Hu & Zhou, 2004). As a continuation of our research work on SARs, we prepared crystals of the title molecule, (I), and investigated its structure.
The molecular structure of (I) is illustrated in Fig. 1. Selected bond lengths and angles are listed in Table 1. A s illustrated in Fig. 1, the three rings of the anthraquinone moiety are not coplanar, because of steric interactions with the benzylidene moiety, wherein the two side phenyl rings form a dihedral angle of 23.0 (1)°. In the central six-membered ring, atoms C11, C12, C13 and C14 are coplanar to within 0.009 (2) Å, with atoms C5 and C10 deviating from the plane by 0.125 (5) and 0.246 (5) Å, respectively, and the ring adopts an asymmetric boat conformation.