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In the title compound, C23H24O8, the central methyl­ene unit that links the two sets of fused rings lies on a crystallographic twofold rotation axis. The isochromene skeleton is not planar, with the pyran ring in an envelope conformation. Intra- and inter­molecular O—H...O hydrogen bonds and weak C—H...O and C—H...π inter­actions stabilize the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680701611X/sj2275sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680701611X/sj2275Isup2.hkl
Contains datablock I

CCDC reference: 647341

Key indicators

  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.045
  • wR factor = 0.108
  • Data-to-parameter ratio = 8.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
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 27.99 From the CIF: _reflns_number_total 2260 Count of symmetry unique reflns 2262 Completeness (_total/calc) 99.91% 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 PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 3 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 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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).

8,8'-Methylenebis(7,10-dihydroxy-1,3,6,6-tetramethyl-3,4-dihydro-1H- benzo[g]isochromen-9-one) top
Crystal data top
C35H40O8Dx = 1.280 Mg m3
Mr = 588.67Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43212Cell parameters from 2260 reflections
Hall symbol: P 4nw 2abwθ = 2.5–28.0°
a = 8.4385 (11) ŵ = 0.09 mm1
c = 42.901 (6) ÅT = 297 K
V = 3054.9 (7) Å3Block, yellow
Z = 40.52 × 0.43 × 0.31 mm
F(000) = 1256
Data collection top
Siemens SMART CCD area-detector
diffractometer
2260 independent reflections
Radiation source: fine-focus sealed tube2063 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
Detector resolution: 8.33 pixels mm-1θmax = 28.0°, θmin = 2.5°
ω scansh = 811
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 119
Tmin = 0.955, Tmax = 0.973l = 4756
18799 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109All H-atom parameters refined
S = 1.15 w = 1/[σ2(Fo2) + (0.0447P)2 + 0.7147P]
where P = (Fo2 + 2Fc2)/3
2260 reflections(Δ/σ)max < 0.001
275 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.15 e Å3
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
xyzUiso*/Ueq
O10.4677 (3)0.9308 (2)0.17258 (4)0.0582 (5)
O20.4769 (2)0.5202 (2)0.11731 (4)0.0520 (4)
O30.4647 (2)0.39680 (19)0.06313 (4)0.0494 (4)
O40.3021 (2)0.6941 (2)0.02377 (4)0.0483 (4)
C10.4647 (3)0.7810 (3)0.15729 (5)0.0452 (5)
C20.5288 (3)1.0592 (3)0.15466 (6)0.0519 (6)
C30.4158 (4)1.0873 (3)0.12776 (6)0.0540 (6)
C40.4027 (3)0.9396 (3)0.10838 (5)0.0423 (5)
C50.3737 (3)0.9490 (3)0.07645 (5)0.0434 (5)
C60.3730 (3)0.8156 (3)0.05769 (5)0.0371 (5)
C70.3471 (3)0.8330 (3)0.02278 (5)0.0385 (5)
C80.3400 (2)0.6763 (3)0.00634 (5)0.0367 (4)
C90.3763 (3)0.5350 (3)0.01925 (5)0.0364 (4)
C100.4177 (3)0.5275 (2)0.05186 (5)0.0376 (5)
C110.4071 (3)0.6681 (3)0.07128 (5)0.0360 (4)
C120.4376 (3)0.6597 (3)0.10374 (5)0.0391 (5)
C130.4310 (3)0.7938 (3)0.12255 (5)0.0399 (5)
C140.3399 (4)0.6840 (5)0.17431 (7)0.0614 (7)
C150.5425 (4)1.2016 (4)0.17597 (7)0.0636 (8)
C160.1947 (4)0.9260 (4)0.01619 (6)0.0589 (8)
C170.4928 (4)0.9210 (3)0.00888 (6)0.0532 (7)
C180.3844 (3)0.3844 (3)0.00000.0389 (7)
H1O20.486 (4)0.445 (4)0.1014 (7)0.074 (10)*
H1O40.321 (4)0.608 (5)0.0370 (7)0.091 (12)*
H10.570 (4)0.729 (3)0.1595 (6)0.053 (7)*
H20.636 (3)1.029 (3)0.1461 (5)0.049 (7)*
H3A0.456 (4)1.175 (4)0.1149 (6)0.065 (9)*
H3B0.317 (4)1.115 (4)0.1364 (6)0.061 (8)*
H50.355 (3)1.052 (3)0.0675 (5)0.043 (6)*
H14A0.334 (4)0.578 (5)0.1668 (8)0.090 (12)*
H14B0.236 (5)0.737 (5)0.1718 (8)0.110 (13)*
H14C0.362 (4)0.693 (4)0.1966 (7)0.066 (8)*
H15A0.430 (4)1.230 (3)0.1842 (6)0.060 (8)*
H15B0.611 (4)1.176 (4)0.1930 (7)0.078 (10)*
H15C0.586 (5)1.299 (5)0.1639 (8)0.099 (12)*
H16A0.100 (4)0.865 (4)0.0255 (7)0.067 (9)*
H16B0.198 (5)1.030 (5)0.0275 (8)0.100 (12)*
H16C0.170 (4)0.940 (4)0.0055 (7)0.073 (9)*
H17A0.511 (4)1.022 (4)0.0188 (7)0.080 (10)*
H17B0.486 (4)0.928 (4)0.0143 (7)0.072 (9)*
H17C0.592 (4)0.852 (4)0.0146 (7)0.078 (10)*
H180.288 (3)0.378 (3)0.0151 (5)0.044 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0751 (13)0.0593 (11)0.0402 (8)0.0010 (10)0.0021 (8)0.0004 (8)
O20.0683 (12)0.0413 (9)0.0464 (9)0.0095 (8)0.0032 (8)0.0132 (8)
O30.0644 (11)0.0353 (8)0.0485 (8)0.0095 (8)0.0046 (8)0.0088 (7)
O40.0576 (11)0.0464 (10)0.0410 (8)0.0093 (8)0.0067 (8)0.0004 (7)
C10.0424 (13)0.0550 (14)0.0380 (10)0.0041 (11)0.0017 (10)0.0057 (10)
C20.0521 (15)0.0560 (15)0.0476 (12)0.0008 (12)0.0036 (11)0.0031 (11)
C30.0654 (18)0.0469 (14)0.0497 (13)0.0062 (13)0.0034 (13)0.0030 (11)
C40.0439 (13)0.0412 (12)0.0418 (10)0.0047 (10)0.0008 (9)0.0013 (9)
C50.0494 (13)0.0347 (11)0.0461 (11)0.0074 (10)0.0016 (10)0.0062 (10)
C60.0356 (11)0.0367 (11)0.0391 (10)0.0042 (9)0.0020 (8)0.0053 (9)
C70.0433 (12)0.0338 (11)0.0384 (10)0.0068 (9)0.0000 (9)0.0061 (9)
C80.0316 (10)0.0404 (11)0.0381 (10)0.0028 (8)0.0004 (8)0.0025 (9)
C90.0306 (10)0.0357 (11)0.0428 (10)0.0002 (8)0.0029 (8)0.0011 (9)
C100.0346 (11)0.0349 (10)0.0433 (10)0.0021 (8)0.0064 (9)0.0070 (9)
C110.0338 (11)0.0346 (10)0.0397 (10)0.0029 (8)0.0026 (8)0.0065 (8)
C120.0372 (11)0.0387 (11)0.0414 (10)0.0031 (9)0.0013 (9)0.0110 (9)
C130.0377 (11)0.0441 (12)0.0380 (10)0.0026 (9)0.0008 (9)0.0062 (9)
C140.0598 (18)0.077 (2)0.0477 (14)0.0044 (16)0.0030 (13)0.0154 (15)
C150.068 (2)0.070 (2)0.0526 (14)0.0046 (17)0.0060 (14)0.0101 (14)
C160.0642 (18)0.0629 (18)0.0495 (14)0.0288 (15)0.0084 (13)0.0024 (13)
C170.0670 (18)0.0458 (14)0.0469 (13)0.0112 (13)0.0061 (12)0.0062 (11)
C180.0337 (9)0.0337 (9)0.0493 (16)0.0022 (12)0.0026 (9)0.0026 (9)
Geometric parameters (Å, º) top
O1—C11.424 (3)C7—C161.532 (3)
O1—C21.425 (3)C7—C171.555 (3)
O2—C121.355 (3)C8—C91.350 (3)
O2—H1O20.93 (3)C9—C101.443 (3)
O3—C101.268 (3)C9—C181.517 (3)
O4—C81.339 (2)C10—C111.453 (3)
O4—H1O40.94 (4)C11—C121.418 (3)
C1—C141.521 (4)C12—C131.390 (3)
C1—C131.521 (3)C14—H14A0.95 (4)
C1—H10.99 (3)C14—H14B0.99 (4)
C2—C151.514 (4)C14—H14C0.98 (3)
C2—C31.516 (4)C15—H15A1.04 (3)
C2—H21.01 (3)C15—H15B0.96 (3)
C3—C41.502 (3)C15—H15C1.04 (4)
C3—H3A0.98 (3)C16—H16A1.03 (3)
C3—H3B0.94 (3)C16—H16B1.01 (4)
C4—C131.393 (3)C16—H16C0.96 (3)
C4—C51.394 (3)C17—H17A0.97 (3)
C5—C61.383 (3)C17—H17B1.00 (3)
C5—H50.97 (3)C17—H17C1.05 (4)
C6—C111.405 (3)C18—C9i1.517 (3)
C6—C71.521 (3)C18—H181.04 (2)
C7—C81.500 (3)
C1—O1—C2115.64 (18)C10—C9—C18118.68 (17)
C12—O2—H1O2107.3 (19)O3—C10—C9118.93 (19)
C8—O4—H1O4117 (2)O3—C10—C11120.73 (19)
O1—C1—C14105.6 (2)C9—C10—C11120.34 (18)
O1—C1—C13113.07 (19)C6—C11—C12119.3 (2)
C14—C1—C13112.3 (2)C6—C11—C10119.91 (18)
O1—C1—H1109.4 (16)C12—C11—C10120.77 (19)
C14—C1—H1109.4 (16)O2—C12—C13117.87 (18)
C13—C1—H1107.0 (15)O2—C12—C11120.6 (2)
O1—C2—C15107.8 (2)C13—C12—C11121.49 (19)
O1—C2—C3107.6 (2)C12—C13—C4118.17 (18)
C15—C2—C3112.6 (2)C12—C13—C1120.24 (19)
O1—C2—H2109.2 (16)C4—C13—C1121.5 (2)
C15—C2—H2110.7 (15)C1—C14—H14A112 (2)
C3—C2—H2109.0 (14)C1—C14—H14B108 (2)
C4—C3—C2109.8 (2)H14A—C14—H14B110 (3)
C4—C3—H3A109.8 (16)C1—C14—H14C106.9 (18)
C2—C3—H3A108.9 (18)H14A—C14—H14C115 (3)
C4—C3—H3B111.0 (19)H14B—C14—H14C104 (3)
C2—C3—H3B107.3 (17)C2—C15—H15A108.4 (16)
H3A—C3—H3B110 (3)C2—C15—H15B109 (2)
C13—C4—C5120.6 (2)H15A—C15—H15B110 (2)
C13—C4—C3118.6 (2)C2—C15—H15C111 (2)
C5—C4—C3120.6 (2)H15A—C15—H15C108 (3)
C6—C5—C4121.7 (2)H15B—C15—H15C110 (3)
C6—C5—H5120.1 (14)C7—C16—H16A109.0 (18)
C4—C5—H5118.1 (14)C7—C16—H16B110 (2)
C5—C6—C11118.61 (18)H16A—C16—H16B106 (3)
C5—C6—C7119.66 (19)C7—C16—H16C115.2 (19)
C11—C6—C7121.59 (19)H16A—C16—H16C105 (2)
C8—C7—C6112.56 (18)H16B—C16—H16C111 (3)
C8—C7—C16109.3 (2)C7—C17—H17A112.1 (19)
C6—C7—C16110.63 (19)C7—C17—H17B111.2 (18)
C8—C7—C17105.76 (18)H17A—C17—H17B114 (3)
C6—C7—C17108.06 (19)C7—C17—H17C106.0 (19)
C16—C7—C17110.4 (2)H17A—C17—H17C105 (3)
O4—C8—C9123.3 (2)H17B—C17—H17C108 (2)
O4—C8—C7111.38 (18)C9i—C18—C9111.9 (2)
C9—C8—C7125.23 (18)C9i—C18—H18108.3 (13)
C8—C9—C10119.44 (19)C9—C18—H18110.4 (14)
C8—C9—C18121.79 (17)
C2—O1—C1—C14157.6 (2)C18—C9—C10—O32.4 (3)
C2—O1—C1—C1334.4 (3)C8—C9—C10—C115.3 (3)
C1—O1—C2—C15172.7 (2)C18—C9—C10—C11178.28 (19)
C1—O1—C2—C365.7 (3)C5—C6—C11—C121.4 (3)
O1—C2—C3—C459.1 (3)C7—C6—C11—C12177.1 (2)
C15—C2—C3—C4177.7 (2)C5—C6—C11—C10175.9 (2)
C2—C3—C4—C1326.4 (4)C7—C6—C11—C100.2 (3)
C2—C3—C4—C5149.2 (2)O3—C10—C11—C6172.4 (2)
C13—C4—C5—C60.4 (4)C9—C10—C11—C66.8 (3)
C3—C4—C5—C6175.0 (3)O3—C10—C11—C124.8 (3)
C4—C5—C6—C111.9 (3)C9—C10—C11—C12175.9 (2)
C4—C5—C6—C7177.7 (2)C6—C11—C12—O2177.4 (2)
C5—C6—C7—C8176.5 (2)C10—C11—C12—O20.1 (3)
C11—C6—C7—C87.8 (3)C6—C11—C12—C131.4 (3)
C5—C6—C7—C1653.9 (3)C10—C11—C12—C13178.7 (2)
C11—C6—C7—C16130.5 (2)O2—C12—C13—C4175.1 (2)
C5—C6—C7—C1767.1 (3)C11—C12—C13—C43.7 (3)
C11—C6—C7—C17108.6 (2)O2—C12—C13—C11.0 (3)
C6—C7—C8—O4174.06 (19)C11—C12—C13—C1179.9 (2)
C16—C7—C8—O450.7 (3)C5—C4—C13—C123.2 (4)
C17—C7—C8—O468.2 (2)C3—C4—C13—C12172.4 (2)
C6—C7—C8—C99.8 (3)C5—C4—C13—C1179.3 (2)
C16—C7—C8—C9133.1 (2)C3—C4—C13—C13.7 (4)
C17—C7—C8—C9108.0 (2)O1—C1—C13—C12174.4 (2)
O4—C8—C9—C10179.2 (2)C14—C1—C13—C1266.2 (3)
C7—C8—C9—C103.5 (3)O1—C1—C13—C41.6 (3)
O4—C8—C9—C183.0 (3)C14—C1—C13—C4117.8 (3)
C7—C8—C9—C18172.8 (2)C8—C9—C18—C9i76.10 (19)
C8—C9—C10—O3174.0 (2)C10—C9—C18—C9i100.22 (19)
Symmetry code: (i) y, x, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H1O2···O30.94 (3)1.70 (3)2.549 (2)149 (3)
O4—H1O4···O3i0.94 (4)1.77 (4)2.690 (2)168 (3)
C14—H14A···O20.95 (4)2.49 (3)3.038 (4)117 (3)
C18—H18···O3i1.04 (2)2.37 (2)2.7938 (19)102.8 (16)
C1—H1···Cg1ii0.99 (3)2.83 (3)3.780 (3)159 (2)
C14—H14B···Cg1iii0.99 (4)2.87 (4)3.729 (4)146 (3)
Symmetry codes: (i) y, x, z; (ii) x+1/2, y+3/2, z+1/4; (iii) x1/2, y+3/2, z+1/4.
 

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