Download citation
Download citation
link to html
The title compound, (E)-3-[2-(3,3,6a,10b-tetra­methyl-8-meth­yl­­eneperhydro­naphtho[2,1-d][1,3]dioxin-7-yl)vin­yl]furan-2(5H)-one, C23H32O4, an andrographolide analogue, was semi-synthesized from 14-de­oxy-11,12-didehydro­andro­grapholide. All the six-membered rings in the structure adopt chair conformations. The crystal structure is stabilized by C—H...O inter­actions, which form a two-dimensional network parallel to the ab plane

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806000699/ci6746sup1.cif
Contains datablocks global, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806000699/ci6746IIsup2.hkl
Contains datablock II

CCDC reference: 298397

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.825 0.984 Tmin(prime) and Tmax expected: 0.958 0.984 RR(prime) = 0.861 Please check that your absorption correction is appropriate. ABSTY02_ALERT_1_C An _exptl_absorpt_correction_type has been given without a literature citation. This should be contained in the _exptl_absorpt_process_details field. Absorption correction given as multi-scan PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.86
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 30.03 From the CIF: _reflns_number_total 3452 Count of symmetry unique reflns 3456 Completeness (_total/calc) 99.88% 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 3 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 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: H.K. Fun and I.A. Razak are supervisors of Jeannie B.-J. Teh whereas J. Stanslas is supervisor of S. R. Sagineedu and N. H. Lajis in this collaborative pulication. UPM is involved in the extraction and synthesis of the title compound and USM is involved in the structure determination. All parties are involved in writing up the manuscript.

1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

(E)-3-[2-(3,3,6a,10b-tetramethyl-8-methyleneperhydronaphtho[2,1-d][1,3]dioxin- 7-yl)vinyl]furan-2(5H)-one top
Crystal data top
C23H32O4F(000) = 808
Mr = 372.49Dx = 1.184 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 7069 reflections
a = 9.1528 (2) Åθ = 1.9–30.0°
b = 10.3440 (2) ŵ = 0.08 mm1
c = 22.0663 (4) ÅT = 297 K
V = 2089.16 (7) Å3Rod, colourless
Z = 40.54 × 0.21 × 0.21 mm
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
3452 independent reflections
Radiation source: fine-focus sealed tube2173 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
Detector resolution: 8.33 pixels mm-1θmax = 30.0°, θmin = 1.9°
ω scansh = 1212
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1414
Tmin = 0.825, Tmax = 0.984l = 3131
27503 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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0499P)2 + 0.0866P]
where P = (Fo2 + 2Fc2)/3
3452 reflections(Δ/σ)max = 0.001
248 parametersΔρmax = 0.12 e Å3
0 restraintsΔρmin = 0.13 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
O10.13560 (16)1.07224 (14)0.06345 (6)0.0628 (4)
O20.10491 (16)1.04586 (15)0.02688 (6)0.0662 (4)
O30.58398 (17)0.17601 (16)0.20847 (7)0.0769 (5)
O40.55754 (19)0.3486 (2)0.26809 (9)0.0993 (6)
C10.0382 (3)1.0920 (2)0.01362 (9)0.0637 (6)
C20.1101 (2)0.9179 (2)0.05082 (9)0.0590 (5)
H2A0.06830.85790.02180.071*
H2B0.21090.89310.05790.071*
C30.02477 (19)0.9113 (2)0.11020 (8)0.0479 (5)
C40.02656 (19)0.77660 (19)0.14203 (8)0.0476 (5)
H40.00910.79430.18310.057*
C50.1809 (2)0.7225 (2)0.15176 (11)0.0645 (6)
H5A0.24490.79070.16620.077*
H5B0.21940.69070.11360.077*
C60.1767 (2)0.6129 (2)0.19793 (11)0.0731 (7)
H6A0.15410.64830.23750.088*
H6B0.27270.57330.20020.088*
C70.0660 (2)0.5109 (2)0.18241 (9)0.0611 (6)
C80.0846 (2)0.56338 (19)0.16858 (8)0.0490 (5)
H80.11810.60690.20550.059*
C90.07770 (19)0.66999 (19)0.11787 (7)0.0452 (4)
C100.22974 (19)0.7287 (2)0.10976 (8)0.0531 (5)
H10A0.26860.75210.14910.064*
H10B0.29420.66430.09220.064*
C110.2277 (2)0.8482 (2)0.06911 (9)0.0576 (5)
H11A0.32630.88090.06420.069*
H11B0.19050.82520.02940.069*
C120.1322 (2)0.9515 (2)0.09682 (8)0.0517 (5)
H120.17600.97080.13630.062*
C130.1914 (2)0.4572 (2)0.15645 (9)0.0544 (5)
H130.18390.41370.11970.065*
C140.2960 (2)0.4206 (2)0.19415 (8)0.0517 (5)
H140.31070.47070.22860.062*
C150.38948 (19)0.3085 (2)0.18619 (8)0.0487 (5)
C160.3841 (2)0.2107 (2)0.14811 (9)0.0576 (5)
H160.31260.19970.11860.069*
C170.5067 (2)0.1209 (2)0.15851 (11)0.0720 (6)
H17A0.47130.03510.16840.086*
H17B0.56880.11540.12300.086*
C180.5145 (2)0.2856 (2)0.22602 (11)0.0626 (6)
C190.0950 (3)1.0332 (3)0.04483 (9)0.0836 (8)
H19A0.09830.94080.04090.125*
H19B0.19141.06550.05290.125*
H19C0.03111.05610.07760.125*
C200.0237 (3)1.2375 (3)0.00872 (13)0.0881 (8)
H20A0.01701.27110.04560.132*
H20B0.03931.25860.02460.132*
H20C0.11841.27500.00210.132*
C210.0916 (3)1.0115 (2)0.15365 (10)0.0698 (6)
H21A0.07701.09680.13760.105*
H21B0.04521.00490.19250.105*
H21C0.19440.99530.15790.105*
C220.0279 (2)0.6070 (2)0.05805 (8)0.0568 (5)
H22A0.01280.67290.02800.085*
H22B0.06170.56090.06460.085*
H22C0.10170.54800.04420.085*
C230.0983 (3)0.3865 (3)0.18327 (13)0.0845 (8)
H23A0.19200.35970.19370.101*
H23B0.02740.32560.17340.101*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0777 (9)0.0520 (9)0.0589 (7)0.0050 (8)0.0153 (7)0.0082 (8)
O20.0710 (9)0.0627 (10)0.0650 (8)0.0142 (9)0.0138 (7)0.0073 (8)
O30.0659 (9)0.0713 (11)0.0935 (10)0.0222 (9)0.0172 (8)0.0030 (10)
O40.0944 (12)0.1037 (15)0.0998 (12)0.0255 (12)0.0441 (11)0.0213 (12)
C10.0788 (14)0.0597 (15)0.0525 (10)0.0114 (13)0.0078 (10)0.0076 (11)
C20.0595 (11)0.0560 (14)0.0615 (11)0.0092 (12)0.0137 (9)0.0027 (11)
C30.0532 (10)0.0468 (12)0.0436 (8)0.0086 (10)0.0037 (8)0.0042 (9)
C40.0488 (9)0.0484 (12)0.0457 (9)0.0070 (10)0.0015 (8)0.0042 (9)
C50.0505 (10)0.0598 (15)0.0833 (14)0.0113 (11)0.0113 (10)0.0011 (13)
C60.0611 (12)0.0641 (15)0.0941 (15)0.0032 (13)0.0236 (12)0.0094 (14)
C70.0638 (12)0.0563 (14)0.0633 (12)0.0009 (12)0.0030 (10)0.0064 (11)
C80.0545 (10)0.0456 (12)0.0471 (9)0.0081 (10)0.0043 (8)0.0008 (9)
C90.0443 (9)0.0473 (12)0.0441 (8)0.0057 (9)0.0041 (7)0.0038 (9)
C100.0453 (9)0.0591 (13)0.0548 (10)0.0071 (10)0.0037 (8)0.0009 (11)
C110.0490 (10)0.0628 (14)0.0609 (10)0.0020 (11)0.0027 (9)0.0062 (11)
C120.0628 (11)0.0475 (12)0.0447 (9)0.0001 (11)0.0118 (8)0.0012 (9)
C130.0616 (11)0.0513 (13)0.0503 (9)0.0096 (11)0.0041 (9)0.0034 (10)
C140.0535 (10)0.0529 (13)0.0487 (9)0.0029 (11)0.0013 (8)0.0000 (10)
C150.0453 (9)0.0513 (12)0.0497 (9)0.0009 (10)0.0021 (8)0.0102 (10)
C160.0562 (11)0.0555 (13)0.0611 (11)0.0043 (12)0.0025 (9)0.0074 (12)
C170.0744 (13)0.0588 (14)0.0827 (14)0.0143 (13)0.0075 (12)0.0036 (14)
C180.0552 (11)0.0613 (15)0.0712 (13)0.0067 (13)0.0104 (11)0.0072 (13)
C190.1032 (18)0.0931 (19)0.0545 (11)0.0179 (18)0.0018 (12)0.0086 (13)
C200.122 (2)0.0637 (16)0.0787 (15)0.0091 (18)0.0170 (15)0.0151 (14)
C210.0923 (16)0.0533 (14)0.0637 (12)0.0194 (14)0.0070 (12)0.0063 (11)
C220.0665 (12)0.0518 (13)0.0520 (10)0.0102 (12)0.0092 (9)0.0079 (10)
C230.0786 (16)0.0621 (16)0.1129 (19)0.0042 (15)0.0097 (15)0.0039 (16)
Geometric parameters (Å, º) top
O1—C11.430 (2)C10—C111.527 (3)
O1—C121.450 (2)C10—H10A0.97
O2—C11.424 (3)C10—H10B0.97
O2—C21.426 (3)C11—C121.510 (3)
O3—C181.356 (3)C11—H11A0.97
O3—C171.428 (3)C11—H11B0.97
O4—C181.201 (3)C12—H120.98
C1—C201.515 (4)C13—C141.323 (3)
C1—C191.518 (3)C13—H130.93
C2—C31.527 (2)C14—C151.452 (3)
C2—H2A0.97C14—H140.93
C2—H2B0.97C15—C161.316 (3)
C3—C121.525 (3)C15—C181.462 (3)
C3—C211.539 (3)C16—C171.475 (3)
C3—C41.560 (3)C16—H160.93
C4—C51.535 (3)C17—H17A0.97
C4—C91.553 (3)C17—H17B0.97
C4—H40.98C19—H19A0.96
C5—C61.525 (3)C19—H19B0.96
C5—H5A0.97C19—H19C0.96
C5—H5B0.97C20—H20A0.96
C6—C71.502 (3)C20—H20B0.96
C6—H6A0.97C20—H20C0.96
C6—H6B0.97C21—H21A0.96
C7—C231.321 (3)C21—H21B0.96
C7—C81.513 (3)C21—H21C0.96
C8—C131.495 (3)C22—H22A0.96
C8—C91.572 (3)C22—H22B0.96
C8—H80.98C22—H22C0.96
C9—C101.529 (3)C23—H23A0.93
C9—C221.541 (2)C23—H23B0.93
C1—O1—C12120.01 (16)C12—C11—C10110.01 (15)
C1—O2—C2114.69 (16)C12—C11—H11A109.7
C18—O3—C17108.78 (17)C10—C11—H11A109.7
O2—C1—O1111.56 (16)C12—C11—H11B109.7
O2—C1—C20105.5 (2)C10—C11—H11B109.7
O1—C1—C20104.5 (2)H11A—C11—H11B108.2
O2—C1—C19110.8 (2)O1—C12—C11113.06 (15)
O1—C1—C19112.48 (18)O1—C12—C3110.69 (16)
C20—C1—C19111.6 (2)C11—C12—C3115.50 (17)
O2—C2—C3110.03 (17)O1—C12—H12105.6
O2—C2—H2A109.7C11—C12—H12105.6
C3—C2—H2A109.7C3—C12—H12105.6
O2—C2—H2B109.7C14—C13—C8124.81 (18)
C3—C2—H2B109.7C14—C13—H13117.6
H2A—C2—H2B108.2C8—C13—H13117.6
C12—C3—C2107.67 (15)C13—C14—C15125.37 (18)
C12—C3—C21108.16 (18)C13—C14—H14117.3
C2—C3—C21107.53 (16)C15—C14—H14117.3
C12—C3—C4109.91 (15)C16—C15—C14132.00 (17)
C2—C3—C4114.89 (16)C16—C15—C18106.77 (19)
C21—C3—C4108.47 (15)C14—C15—C18121.20 (19)
C5—C4—C9110.79 (17)C15—C16—C17110.86 (18)
C5—C4—C3113.46 (15)C15—C16—H16124.6
C9—C4—C3118.24 (15)C17—C16—H16124.6
C5—C4—H4104.2O3—C17—C16104.22 (18)
C9—C4—H4104.2O3—C17—H17A110.9
C3—C4—H4104.2C16—C17—H17A110.9
C6—C5—C4109.97 (17)O3—C17—H17B110.9
C6—C5—H5A109.7C16—C17—H17B110.9
C4—C5—H5A109.7H17A—C17—H17B108.9
C6—C5—H5B109.7O4—C18—O3121.4 (2)
C4—C5—H5B109.7O4—C18—C15129.3 (2)
H5A—C5—H5B108.2O3—C18—C15109.3 (2)
C7—C6—C5112.75 (18)C1—C19—H19A109.5
C7—C6—H6A109.0C1—C19—H19B109.5
C5—C6—H6A109.0H19A—C19—H19B109.5
C7—C6—H6B109.0C1—C19—H19C109.5
C5—C6—H6B109.0H19A—C19—H19C109.5
H6A—C6—H6B107.8H19B—C19—H19C109.5
C23—C7—C6122.0 (2)C1—C20—H20A109.5
C23—C7—C8123.8 (2)C1—C20—H20B109.5
C6—C7—C8114.14 (19)H20A—C20—H20B109.5
C13—C8—C7111.64 (17)C1—C20—H20C109.5
C13—C8—C9114.47 (15)H20A—C20—H20C109.5
C7—C8—C9111.01 (14)H20B—C20—H20C109.5
C13—C8—H8106.4C3—C21—H21A109.5
C7—C8—H8106.4C3—C21—H21B109.5
C9—C8—H8106.4H21A—C21—H21B109.5
C10—C9—C22109.67 (15)C3—C21—H21C109.5
C10—C9—C4108.52 (15)H21A—C21—H21C109.5
C22—C9—C4114.38 (15)H21B—C21—H21C109.5
C10—C9—C8108.97 (14)C9—C22—H22A109.5
C22—C9—C8108.97 (16)C9—C22—H22B109.5
C4—C9—C8106.16 (14)H22A—C22—H22B109.5
C11—C10—C9112.26 (15)C9—C22—H22C109.5
C11—C10—H10A109.2H22A—C22—H22C109.5
C9—C10—H10A109.2H22B—C22—H22C109.5
C11—C10—H10B109.2C7—C23—H23A120.0
C9—C10—H10B109.2C7—C23—H23B120.0
H10A—C10—H10B107.9H23A—C23—H23B120.0
C2—O2—C1—O149.4 (2)C13—C8—C9—C2261.9 (2)
C2—O2—C1—C20162.33 (17)C7—C8—C9—C2265.6 (2)
C2—O2—C1—C1976.8 (2)C13—C8—C9—C4174.45 (15)
C12—O1—C1—O242.2 (2)C7—C8—C9—C458.06 (19)
C12—O1—C1—C20155.79 (19)C22—C9—C10—C1170.4 (2)
C12—O1—C1—C1983.0 (2)C4—C9—C10—C1155.19 (19)
C1—O2—C2—C360.4 (2)C8—C9—C10—C11170.38 (15)
O2—C2—C3—C1259.1 (2)C9—C10—C11—C1260.9 (2)
O2—C2—C3—C2157.3 (2)C1—O1—C12—C1186.7 (2)
O2—C2—C3—C4178.12 (15)C1—O1—C12—C344.6 (2)
C12—C3—C4—C5174.50 (17)C10—C11—C12—O1174.73 (15)
C2—C3—C4—C552.9 (2)C10—C11—C12—C356.3 (2)
C21—C3—C4—C567.4 (2)C2—C3—C12—O150.2 (2)
C12—C3—C4—C942.3 (2)C21—C3—C12—O165.74 (18)
C2—C3—C4—C979.3 (2)C4—C3—C12—O1176.00 (13)
C21—C3—C4—C9160.32 (16)C2—C3—C12—C1179.9 (2)
C9—C4—C5—C660.3 (2)C21—C3—C12—C11164.17 (17)
C3—C4—C5—C6163.94 (16)C4—C3—C12—C1145.9 (2)
C4—C5—C6—C752.4 (3)C7—C8—C13—C14106.7 (2)
C5—C6—C7—C23132.1 (3)C9—C8—C13—C14126.2 (2)
C5—C6—C7—C850.4 (3)C8—C13—C14—C15172.48 (18)
C23—C7—C8—C130.3 (3)C13—C14—C15—C1610.6 (3)
C6—C7—C8—C13177.24 (17)C13—C14—C15—C18171.7 (2)
C23—C7—C8—C9128.7 (2)C14—C15—C16—C17179.8 (2)
C6—C7—C8—C953.7 (2)C18—C15—C16—C172.3 (2)
C5—C4—C9—C10179.34 (16)C18—O3—C17—C160.4 (2)
C3—C4—C9—C1047.3 (2)C15—C16—C17—O31.2 (2)
C5—C4—C9—C2257.9 (2)C17—O3—C18—O4178.8 (2)
C3—C4—C9—C2275.5 (2)C17—O3—C18—C151.7 (2)
C5—C4—C9—C862.33 (19)C16—C15—C18—O4178.1 (3)
C3—C4—C9—C8164.26 (14)C14—C15—C18—O40.1 (3)
C13—C8—C9—C1057.7 (2)C16—C15—C18—O32.5 (2)
C7—C8—C9—C10174.76 (17)C14—C15—C18—O3179.28 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16···O1i0.932.423.273 (2)153
C17—H17A···O4ii0.972.403.302 (3)155
Symmetry codes: (i) x, y1, z; (ii) x+1, y1/2, z+1/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds