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In the title compound, C30H24O4, the chromone system is essentially planar. There are inter­molecular C—H...O and C—H...π inter­actions in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806024275/bh2025sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806024275/bh2025Isup2.hkl
Contains datablock I

CCDC reference: 618120

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.062
  • wR factor = 0.153
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 49 Perc. PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.56 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C29 - C30 .. 6.49 su PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT480_ALERT_4_C Long H...A H-Bond Reported H19 .. O2 .. 2.63 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H20 .. O2 .. 2.61 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. CGA .. 2.99 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H17A .. CGB .. 2.95 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

8-Benzyl-5,7-bis(benzyloxy)-4H-benzopyran-4-one top
Crystal data top
C30H24O4F(000) = 944
Mr = 448.49Dx = 1.278 Mg m3
Monoclinic, P21/cMelting point: 433.2 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 9.723 (2) ÅCell parameters from 25 reflections
b = 9.746 (2) Åθ = 10–13°
c = 24.698 (5) ŵ = 0.08 mm1
β = 95.15 (3)°T = 293 K
V = 2330.9 (8) Å3Block, colourless
Z = 40.35 × 0.32 × 0.21 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
2228 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.078
Graphite monochromatorθmax = 26.0°, θmin = 1.7°
ω/2θ scansh = 011
Absorption correction: ψ scan
(XCAD4; Harms & Wocadlo, 1995)
k = 012
Tmin = 0.959, Tmax = 0.983l = 3030
4828 measured reflections3 standard reflections every 200 reflections
4549 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.062H-atom parameters constrained
wR(F2) = 0.153 w = 1/[σ2(Fo2) + (0.052P)2 + 0.32P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
4549 reflectionsΔρmax = 0.17 e Å3
308 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0250 (15)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.3663 (2)0.1266 (2)0.18037 (8)0.0656 (6)
O20.2169 (3)0.4154 (3)0.07149 (10)0.0917 (8)
O30.4033 (2)0.3326 (2)0.00707 (8)0.0592 (6)
O40.71410 (19)0.0221 (2)0.07821 (8)0.0574 (6)
C10.2616 (3)0.2137 (4)0.18976 (15)0.0754 (10)
H10.22340.20690.22280.090*
C20.2113 (4)0.3068 (4)0.15492 (16)0.0747 (10)
H20.13850.36150.16410.090*
C30.2649 (3)0.3271 (4)0.10326 (14)0.0624 (9)
C40.3799 (3)0.2359 (3)0.09280 (12)0.0493 (7)
C50.4509 (3)0.2410 (3)0.04556 (12)0.0469 (7)
C60.5621 (3)0.1555 (3)0.03970 (11)0.0484 (7)
H60.60860.15990.00840.058*
C70.6042 (3)0.0629 (3)0.08068 (12)0.0471 (7)
C80.5367 (3)0.0498 (3)0.12740 (11)0.0485 (7)
C90.4269 (3)0.1394 (3)0.13207 (12)0.0501 (8)
C100.4659 (3)0.3404 (3)0.04281 (12)0.0568 (8)
H10A0.46790.25020.05930.068*
H10B0.56000.37320.03620.068*
C110.3831 (3)0.4371 (3)0.08001 (13)0.0564 (8)
C120.2665 (3)0.5024 (3)0.06507 (14)0.0692 (9)
H120.23710.48710.03080.083*
C130.1926 (4)0.5910 (4)0.10101 (18)0.0865 (12)
H130.11370.63420.09080.104*
C140.2358 (5)0.6148 (4)0.1512 (2)0.0961 (14)
H140.18600.67380.17520.115*
C150.3523 (5)0.5519 (5)0.16639 (17)0.0960 (13)
H150.38220.56930.20040.115*
C160.4258 (4)0.4621 (4)0.13091 (15)0.0771 (10)
H160.50420.41860.14150.093*
C170.8062 (3)0.0011 (3)0.03703 (13)0.0637 (9)
H17A0.83120.09740.03580.076*
H17B0.76290.02530.00170.076*
C180.9324 (3)0.0855 (3)0.05192 (12)0.0504 (7)
C190.9383 (3)0.2170 (3)0.03252 (13)0.0618 (9)
H190.86510.25110.00960.074*
C201.0508 (4)0.2989 (3)0.04651 (14)0.0709 (10)
H201.05320.38830.03350.085*
C211.1592 (3)0.2485 (4)0.07952 (14)0.0700 (10)
H211.23560.30360.08900.084*
C221.1556 (4)0.1174 (4)0.09870 (14)0.0739 (10)
H221.22990.08320.12100.089*
C231.0415 (4)0.0351 (3)0.08495 (13)0.0652 (9)
H231.03900.05420.09810.078*
C240.5859 (3)0.0508 (3)0.17140 (12)0.0584 (8)
H24A0.51050.07080.19330.070*
H24B0.61200.13580.15470.070*
C250.7069 (4)0.0019 (3)0.20766 (12)0.0590 (8)
C260.8391 (4)0.0463 (4)0.20333 (14)0.0768 (10)
H260.85360.11360.17770.092*
C270.9495 (5)0.0034 (6)0.23623 (19)0.1049 (15)
H271.03760.03050.23260.126*
C280.9314 (7)0.1011 (6)0.2739 (2)0.120 (2)
H281.00620.13390.29620.144*
C290.8009 (7)0.1514 (5)0.27860 (18)0.1156 (17)
H290.78770.21940.30400.139*
C300.6889 (5)0.1014 (4)0.24576 (15)0.0860 (12)
H300.60100.13550.24960.103*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0695 (15)0.0651 (15)0.0656 (15)0.0081 (12)0.0247 (12)0.0011 (11)
O20.101 (2)0.0878 (19)0.0867 (19)0.0540 (16)0.0111 (15)0.0021 (15)
O30.0611 (13)0.0569 (13)0.0591 (13)0.0160 (11)0.0027 (10)0.0093 (11)
O40.0612 (13)0.0526 (13)0.0613 (13)0.0178 (11)0.0211 (11)0.0148 (10)
C10.072 (2)0.082 (3)0.077 (3)0.009 (2)0.028 (2)0.019 (2)
C20.068 (2)0.075 (3)0.083 (3)0.021 (2)0.015 (2)0.019 (2)
C30.063 (2)0.058 (2)0.065 (2)0.0107 (18)0.0032 (18)0.0160 (18)
C40.0481 (17)0.0431 (17)0.0569 (19)0.0057 (15)0.0050 (15)0.0096 (15)
C50.0452 (17)0.0386 (16)0.0559 (19)0.0001 (14)0.0008 (14)0.0034 (14)
C60.0530 (18)0.0446 (17)0.0484 (17)0.0070 (15)0.0093 (14)0.0038 (14)
C70.0483 (17)0.0353 (16)0.0584 (19)0.0071 (14)0.0082 (15)0.0005 (14)
C80.0514 (17)0.0449 (17)0.0499 (18)0.0019 (15)0.0081 (14)0.0040 (14)
C90.0509 (18)0.0476 (18)0.0534 (19)0.0008 (15)0.0132 (15)0.0048 (15)
C100.065 (2)0.0474 (18)0.057 (2)0.0051 (16)0.0028 (16)0.0029 (15)
C110.058 (2)0.0437 (18)0.064 (2)0.0074 (16)0.0110 (16)0.0070 (16)
C120.068 (2)0.056 (2)0.081 (2)0.0024 (19)0.0068 (19)0.0117 (18)
C130.074 (3)0.077 (3)0.103 (3)0.012 (2)0.016 (2)0.020 (2)
C140.096 (3)0.078 (3)0.107 (4)0.007 (3)0.033 (3)0.034 (3)
C150.110 (3)0.099 (3)0.076 (3)0.015 (3)0.011 (3)0.029 (2)
C160.085 (3)0.073 (2)0.072 (2)0.003 (2)0.000 (2)0.016 (2)
C170.064 (2)0.063 (2)0.067 (2)0.0186 (18)0.0231 (17)0.0172 (17)
C180.0519 (18)0.0493 (19)0.0516 (18)0.0087 (15)0.0135 (15)0.0098 (15)
C190.058 (2)0.052 (2)0.075 (2)0.0057 (17)0.0022 (16)0.0051 (17)
C200.075 (2)0.053 (2)0.086 (3)0.018 (2)0.013 (2)0.0028 (19)
C210.055 (2)0.077 (3)0.080 (3)0.020 (2)0.0133 (18)0.021 (2)
C220.062 (2)0.082 (3)0.075 (2)0.014 (2)0.0091 (18)0.012 (2)
C230.079 (2)0.052 (2)0.066 (2)0.0007 (19)0.0098 (19)0.0009 (17)
C240.068 (2)0.0504 (19)0.059 (2)0.0061 (17)0.0157 (17)0.0064 (16)
C250.079 (2)0.053 (2)0.0462 (18)0.0013 (18)0.0086 (16)0.0126 (16)
C260.077 (3)0.090 (3)0.063 (2)0.001 (2)0.007 (2)0.014 (2)
C270.089 (3)0.144 (4)0.079 (3)0.027 (3)0.004 (3)0.032 (3)
C280.145 (5)0.124 (5)0.083 (4)0.055 (4)0.034 (4)0.033 (3)
C290.190 (5)0.083 (3)0.070 (3)0.009 (4)0.011 (4)0.003 (2)
C300.120 (3)0.077 (3)0.059 (2)0.009 (2)0.006 (2)0.001 (2)
Geometric parameters (Å, º) top
O1—C11.361 (4)C15—C161.390 (5)
O1—C91.382 (3)C15—H150.9300
O2—C31.229 (4)C16—H160.9300
O3—C51.355 (3)C17—C181.507 (4)
O3—C101.424 (3)C17—H17A0.9700
O4—C71.358 (3)C17—H17B0.9700
O4—C171.432 (3)C18—C231.370 (4)
C1—C21.315 (5)C18—C191.371 (4)
C1—H10.9300C19—C201.374 (4)
C2—C31.435 (5)C19—H190.9300
C2—H20.9300C20—C211.364 (4)
C3—C41.469 (4)C20—H200.9300
C4—C91.398 (4)C21—C221.364 (5)
C4—C51.409 (4)C21—H210.9300
C5—C61.383 (4)C22—C231.387 (4)
C6—C71.390 (4)C22—H220.9300
C6—H60.9300C23—H230.9300
C7—C81.384 (4)C24—C251.503 (4)
C8—C91.392 (4)C24—H24A0.9700
C8—C241.509 (4)C24—H24B0.9700
C10—C111.499 (4)C25—C301.373 (4)
C10—H10A0.9700C25—C261.382 (4)
C10—H10B0.9700C26—C271.375 (5)
C11—C121.379 (4)C26—H260.9300
C11—C161.381 (4)C27—C281.353 (6)
C12—C131.391 (4)C27—H270.9300
C12—H120.9300C28—C291.374 (6)
C13—C141.363 (5)C28—H280.9300
C13—H130.9300C29—C301.387 (6)
C14—C151.370 (5)C29—H290.9300
C14—H140.9300C30—H300.9300
C1—O1—C9118.3 (3)C11—C16—C15120.3 (4)
C5—O3—C10119.8 (2)C11—C16—H16119.8
C7—O4—C17118.7 (2)C15—C16—H16119.8
C2—C1—O1124.0 (3)O4—C17—C18106.6 (2)
C2—C1—H1118.0O4—C17—H17A110.4
O1—C1—H1118.0C18—C17—H17A110.4
C1—C2—C3122.2 (3)O4—C17—H17B110.4
C1—C2—H2118.9C18—C17—H17B110.4
C3—C2—H2118.9H17A—C17—H17B108.6
O2—C3—C2121.1 (3)C23—C18—C19119.3 (3)
O2—C3—C4124.3 (3)C23—C18—C17120.9 (3)
C2—C3—C4114.6 (3)C19—C18—C17119.8 (3)
C9—C4—C5116.4 (3)C18—C19—C20120.8 (3)
C9—C4—C3119.4 (3)C18—C19—H19119.6
C5—C4—C3124.1 (3)C20—C19—H19119.6
O3—C5—C6123.0 (3)C21—C20—C19119.7 (3)
O3—C5—C4116.3 (2)C21—C20—H20120.1
C6—C5—C4120.7 (3)C19—C20—H20120.1
C5—C6—C7119.8 (3)C22—C21—C20120.2 (3)
C5—C6—H6120.1C22—C21—H21119.9
C7—C6—H6120.1C20—C21—H21119.9
O4—C7—C8114.5 (2)C21—C22—C23120.1 (3)
O4—C7—C6123.0 (3)C21—C22—H22119.9
C8—C7—C6122.5 (3)C23—C22—H22119.9
C7—C8—C9115.8 (3)C18—C23—C22119.9 (3)
C7—C8—C24121.1 (3)C18—C23—H23120.1
C9—C8—C24122.9 (3)C22—C23—H23120.1
O1—C9—C8113.9 (3)C25—C24—C8112.8 (2)
O1—C9—C4121.4 (3)C25—C24—H24A109.0
C8—C9—C4124.7 (3)C8—C24—H24A109.0
O3—C10—C11108.5 (2)C25—C24—H24B109.0
O3—C10—H10A110.0C8—C24—H24B109.0
C11—C10—H10A110.0H24A—C24—H24B107.8
O3—C10—H10B110.0C30—C25—C26118.0 (4)
C11—C10—H10B110.0C30—C25—C24120.6 (3)
H10A—C10—H10B108.4C26—C25—C24121.4 (3)
C12—C11—C16119.0 (3)C27—C26—C25121.1 (4)
C12—C11—C10122.4 (3)C27—C26—H26119.4
C16—C11—C10118.7 (3)C25—C26—H26119.4
C11—C12—C13120.4 (4)C28—C27—C26120.7 (5)
C11—C12—H12119.8C28—C27—H27119.6
C13—C12—H12119.8C26—C27—H27119.6
C14—C13—C12120.1 (4)C27—C28—C29119.2 (5)
C14—C13—H13119.9C27—C28—H28120.4
C12—C13—H13119.9C29—C28—H28120.4
C13—C14—C15120.2 (4)C28—C29—C30120.5 (5)
C13—C14—H14119.9C28—C29—H29119.7
C15—C14—H14119.9C30—C29—H29119.7
C14—C15—C16120.0 (4)C25—C30—C29120.5 (4)
C14—C15—H15120.0C25—C30—H30119.8
C16—C15—H15120.0C29—C30—H30119.8
C9—O1—C1—C22.2 (5)C5—O3—C10—C11173.4 (2)
O1—C1—C2—C31.2 (6)O3—C10—C11—C120.4 (4)
C1—C2—C3—O2179.5 (3)O3—C10—C11—C16179.2 (3)
C1—C2—C3—C40.1 (5)C16—C11—C12—C130.5 (5)
O2—C3—C4—C9179.6 (3)C10—C11—C12—C13179.8 (3)
C2—C3—C4—C90.3 (4)C11—C12—C13—C140.5 (5)
O2—C3—C4—C51.5 (5)C12—C13—C14—C150.2 (6)
C2—C3—C4—C5177.9 (3)C13—C14—C15—C160.9 (6)
C10—O3—C5—C62.1 (4)C12—C11—C16—C150.1 (5)
C10—O3—C5—C4177.5 (2)C10—C11—C16—C15179.6 (3)
C9—C4—C5—O3178.6 (2)C14—C15—C16—C110.9 (6)
C3—C4—C5—O33.2 (4)C7—O4—C17—C18167.4 (2)
C9—C4—C5—C61.0 (4)O4—C17—C18—C2389.1 (3)
C3—C4—C5—C6177.2 (3)O4—C17—C18—C1990.5 (3)
O3—C5—C6—C7179.3 (2)C23—C18—C19—C201.1 (5)
C4—C5—C6—C70.3 (4)C17—C18—C19—C20178.6 (3)
C17—O4—C7—C8168.2 (3)C18—C19—C20—C210.9 (5)
C17—O4—C7—C612.0 (4)C19—C20—C21—C220.2 (5)
C5—C6—C7—O4178.6 (3)C20—C21—C22—C230.4 (5)
C5—C6—C7—C81.6 (4)C19—C18—C23—C220.5 (5)
O4—C7—C8—C9177.6 (2)C17—C18—C23—C22179.1 (3)
C6—C7—C8—C92.6 (4)C21—C22—C23—C180.2 (5)
O4—C7—C8—C240.8 (4)C7—C8—C24—C2579.8 (3)
C6—C7—C8—C24179.4 (3)C9—C8—C24—C2596.7 (3)
C1—O1—C9—C8177.4 (3)C8—C24—C25—C3074.3 (4)
C1—O1—C9—C42.0 (4)C8—C24—C25—C26104.8 (3)
C7—C8—C9—O1177.4 (2)C30—C25—C26—C270.1 (5)
C24—C8—C9—O10.7 (4)C24—C25—C26—C27179.3 (3)
C7—C8—C9—C42.0 (4)C25—C26—C27—C280.1 (6)
C24—C8—C9—C4178.6 (3)C26—C27—C28—C290.5 (7)
C5—C4—C9—O1179.1 (2)C27—C28—C29—C300.8 (7)
C3—C4—C9—O10.8 (4)C26—C25—C30—C290.1 (5)
C5—C4—C9—C80.2 (4)C24—C25—C30—C29179.0 (3)
C3—C4—C9—C8178.5 (3)C28—C29—C30—C250.6 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C19—H19···O2i0.932.633.453 (3)148
C20—H20···O2ii0.932.613.250 (3)127
C2—H2···Cg(A)iii0.932.993.545 (4)120
C17—H17A···Cg(B)iv0.972.953.430 (3)112
Symmetry codes: (i) x+1, y, z; (ii) x+1, y1, z; (iii) x+1, y+1/2, z+1/2; (iv) x+2, y, z.
 

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