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The structure of bharangin tri­acetate [systematic name: 6,10-bis­(acetyl­oxy)-8-iso­propyl-4,4,11a-tri­methyl-2-oxo-2,3,4,6,11,11a-hexa­hydro­benzo­[5,6]­cyclo­hepta­[1,2-b]­pyran-9-yl ace­tate], C26H32O8, a tricyclic diterpenoid, contains a seven-membered cyclohepta­diene ring forming two planar parts, a six-membered δ-lactone ring in a boat conformation and a planar benzene ring. The structure is stabilized by intra- and intermolecular C—H...O interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805000838/bt6576sup1.cif
Contains datablocks II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805000838/bt6576IIsup2.hkl
Contains datablock I

CCDC reference: 263716

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.053
  • wR factor = 0.128
  • Data-to-parameter ratio = 8.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.78 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.36 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C18 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C23 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C25 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
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 25.00 From the CIF: _reflns_number_total 2528 Count of symmetry unique reflns 2528 Completeness (_total/calc) 100.00% 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 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

6,10-bis(acetyloxy)-8-isopropyl-4,4,11a-trimethyl-2-oxo-2,3,4,6,11,11a- hexahydrobenzo[5,6]cyclohepta[1,2-b]pyran-9-yl acetate top
Crystal data top
C26H32O8F(000) = 1008
Mr = 472.52Dx = 1.244 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5917 reflections
a = 10.4278 (5) Åθ = 2.3–24.8°
b = 13.3828 (6) ŵ = 0.09 mm1
c = 18.0857 (9) ÅT = 273 K
V = 2523.9 (2) Å3Transparent needles, colorless
Z = 40.20 × 0.15 × 0.10 mm
Data collection top
CCD Area Detector
diffractometer
2435 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
Graphite monochromatorθmax = 25.0°, θmin = 1.9°
ω scansh = 1212
18391 measured reflectionsk = 1515
2528 independent reflectionsl = 2121
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H-atom parameters constrained
S = 1.25 w = 1/[σ2(Fo2) + (0.0582P)2 + 0.6697P]
where P = (Fo2 + 2Fc2)/3
2528 reflections(Δ/σ)max < 0.001
315 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.14 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2154 (3)0.7694 (2)1.02533 (17)0.0388 (7)
H10.14770.72851.04760.047*
C20.1713 (3)0.8759 (3)1.02743 (18)0.0425 (8)
H20.11020.88861.06370.051*
C30.2021 (3)0.9552 (2)0.98784 (19)0.0412 (8)
C40.2989 (3)0.9591 (2)0.92547 (19)0.0419 (8)
C50.3924 (3)0.8715 (2)0.92494 (18)0.0382 (7)
H5A0.46150.88610.89070.046*
H5B0.42950.86450.97380.046*
C60.3307 (3)0.7739 (2)0.90315 (18)0.0371 (7)
C70.2462 (3)0.7250 (2)0.95092 (17)0.0363 (7)
C80.1881 (3)0.6365 (2)0.92993 (17)0.0377 (7)
H80.13570.60390.96380.045*
C90.2048 (3)0.5940 (2)0.86040 (18)0.0402 (8)
C100.2869 (3)0.6442 (2)0.81278 (18)0.0403 (8)
C110.3499 (3)0.7308 (2)0.83437 (18)0.0398 (7)
C120.1393 (4)1.0564 (3)1.0091 (2)0.0577 (10)
C130.1953 (4)1.1416 (3)0.9624 (3)0.0665 (12)
H13A0.15661.14010.91370.080*
H13B0.17331.20500.98520.080*
C140.3375 (5)1.1351 (3)0.9546 (2)0.0607 (11)
C150.0067 (4)1.0507 (4)0.9961 (4)0.101 (2)
H15A0.04461.11461.00630.151*
H15B0.04331.00131.02830.151*
H15C0.02311.03270.94560.151*
C160.1687 (6)1.0799 (3)1.0902 (3)0.0837 (16)
H16A0.25981.08521.09680.126*
H16B0.13601.02721.12090.126*
H16C0.12881.14191.10360.126*
C170.2408 (4)0.9714 (3)0.8481 (2)0.0577 (10)
H17A0.17431.02100.84960.087*
H17B0.20530.90880.83210.087*
H17C0.30640.99210.81410.087*
C180.3309 (4)0.6883 (2)1.1220 (2)0.0466 (8)
C190.4464 (5)0.6917 (4)1.1689 (3)0.0800 (15)
H19A0.43640.74271.20580.120*
H19B0.51990.70651.13890.120*
H19C0.45810.62821.19260.120*
C200.1325 (4)0.5003 (3)0.8378 (2)0.0491 (9)
H200.17480.47320.79380.059*
C210.0049 (4)0.5256 (4)0.8166 (3)0.0741 (13)
H21A0.04670.55790.85740.111*
H21B0.05010.46540.80430.111*
H21C0.00470.56960.77470.111*
C220.1357 (5)0.4198 (3)0.8971 (3)0.0711 (13)
H22A0.22300.40650.91070.107*
H22B0.09710.35980.87830.107*
H22C0.08900.44220.93970.107*
C230.2441 (4)0.6510 (3)0.6855 (2)0.0578 (10)
C240.2943 (5)0.6175 (4)0.6129 (2)0.0713 (13)
H24A0.24420.64680.57400.107*
H24B0.28900.54600.60980.107*
H24C0.38210.63790.60800.107*
C250.5453 (4)0.7431 (4)0.7696 (2)0.0561 (10)
C260.6121 (5)0.8042 (5)0.7136 (2)0.0858 (16)
H26A0.69910.78170.70890.129*
H26B0.61130.87300.72860.129*
H26C0.56920.79760.66690.129*
O10.3854 (3)1.04403 (17)0.93973 (14)0.0522 (6)
O20.4099 (4)1.2031 (2)0.9621 (2)0.0865 (11)
O30.3282 (2)0.76278 (16)1.07346 (12)0.0427 (6)
O40.2491 (4)0.6263 (2)1.1271 (2)0.0881 (11)
O50.3112 (2)0.60797 (18)0.74178 (12)0.0496 (6)
O60.1604 (4)0.7089 (3)0.69661 (18)0.0997 (13)
O70.4256 (2)0.78043 (18)0.78200 (13)0.0483 (6)
O80.5862 (3)0.6718 (3)0.80110 (18)0.0849 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0388 (16)0.0385 (17)0.0391 (17)0.0052 (15)0.0013 (14)0.0006 (14)
C20.0409 (17)0.0439 (18)0.0426 (18)0.0022 (16)0.0067 (15)0.0085 (15)
C30.0361 (17)0.0399 (17)0.0477 (18)0.0011 (15)0.0036 (15)0.0046 (15)
C40.0425 (18)0.0360 (16)0.0472 (18)0.0057 (15)0.0058 (16)0.0012 (15)
C50.0341 (16)0.0418 (17)0.0387 (17)0.0034 (14)0.0046 (14)0.0002 (14)
C60.0347 (15)0.0346 (15)0.0421 (17)0.0051 (14)0.0014 (14)0.0006 (14)
C70.0328 (15)0.0364 (16)0.0397 (17)0.0044 (14)0.0042 (14)0.0019 (14)
C80.0378 (16)0.0351 (16)0.0401 (17)0.0024 (14)0.0062 (14)0.0023 (14)
C90.0407 (17)0.0350 (16)0.0448 (18)0.0039 (15)0.0024 (15)0.0032 (14)
C100.0424 (18)0.0410 (17)0.0375 (17)0.0037 (15)0.0048 (15)0.0015 (14)
C110.0385 (17)0.0395 (17)0.0416 (17)0.0013 (15)0.0046 (14)0.0023 (15)
C120.052 (2)0.0382 (18)0.083 (3)0.0122 (17)0.002 (2)0.0071 (19)
C130.076 (3)0.0367 (19)0.086 (3)0.010 (2)0.016 (3)0.004 (2)
C140.081 (3)0.0342 (19)0.067 (3)0.007 (2)0.001 (2)0.0003 (18)
C150.051 (3)0.056 (3)0.195 (6)0.020 (2)0.001 (3)0.018 (4)
C160.122 (4)0.050 (2)0.079 (3)0.009 (3)0.026 (3)0.016 (2)
C170.069 (3)0.050 (2)0.054 (2)0.001 (2)0.008 (2)0.0078 (17)
C180.051 (2)0.0374 (18)0.051 (2)0.0024 (16)0.0070 (17)0.0063 (16)
C190.072 (3)0.085 (3)0.083 (3)0.004 (3)0.009 (3)0.041 (3)
C200.057 (2)0.0401 (18)0.050 (2)0.0033 (17)0.0111 (18)0.0113 (16)
C210.058 (3)0.073 (3)0.091 (3)0.015 (2)0.002 (2)0.028 (3)
C220.095 (3)0.046 (2)0.072 (3)0.014 (2)0.009 (3)0.005 (2)
C230.052 (2)0.076 (3)0.045 (2)0.011 (2)0.0014 (19)0.003 (2)
C240.091 (3)0.081 (3)0.041 (2)0.032 (3)0.006 (2)0.004 (2)
C250.041 (2)0.090 (3)0.0369 (19)0.008 (2)0.0010 (15)0.000 (2)
C260.056 (2)0.146 (5)0.055 (2)0.024 (3)0.010 (2)0.017 (3)
O10.0560 (15)0.0345 (12)0.0660 (16)0.0103 (12)0.0003 (13)0.0070 (12)
O20.098 (2)0.0422 (15)0.119 (3)0.0268 (17)0.013 (2)0.0111 (17)
O30.0479 (13)0.0391 (12)0.0411 (12)0.0061 (11)0.0028 (11)0.0054 (10)
O40.094 (2)0.0604 (19)0.110 (3)0.025 (2)0.015 (2)0.0361 (19)
O50.0586 (15)0.0504 (14)0.0398 (12)0.0023 (13)0.0090 (12)0.0068 (11)
O60.088 (2)0.147 (3)0.064 (2)0.045 (3)0.0018 (19)0.010 (2)
O70.0503 (14)0.0501 (13)0.0445 (13)0.0049 (12)0.0139 (11)0.0019 (11)
O80.0549 (18)0.126 (3)0.074 (2)0.0165 (19)0.0066 (16)0.028 (2)
Geometric parameters (Å, º) top
C1—O31.466 (4)C15—H15C0.9600
C1—C21.498 (5)C16—H16A0.9600
C1—C71.506 (4)C16—H16B0.9600
C1—H10.9800C16—H16C0.9600
C2—C31.320 (5)C17—H17A0.9600
C2—H20.9300C17—H17B0.9600
C3—C41.514 (5)C17—H17C0.9600
C3—C121.553 (5)C18—O41.193 (5)
C4—O11.474 (4)C18—O31.328 (4)
C4—C51.524 (5)C18—C191.474 (6)
C4—C171.534 (5)C19—H19A0.9600
C5—C61.509 (5)C19—H19B0.9600
C5—H5A0.9700C19—H19C0.9600
C5—H5B0.9700C20—C221.521 (6)
C6—C111.386 (4)C20—C211.522 (6)
C6—C71.397 (4)C20—H200.9800
C7—C81.383 (5)C21—H21A0.9600
C8—C91.391 (5)C21—H21B0.9600
C8—H80.9300C21—H21C0.9600
C9—C101.388 (5)C22—H22A0.9600
C9—C201.520 (5)C22—H22B0.9600
C10—C111.388 (5)C22—H22C0.9600
C10—O51.396 (4)C23—O61.185 (5)
C11—O71.401 (4)C23—O51.363 (5)
C12—C161.531 (7)C23—C241.482 (6)
C12—C131.535 (6)C24—H24A0.9600
C12—C151.542 (6)C24—H24B0.9600
C13—C141.492 (7)C24—H24C0.9600
C13—H13A0.9700C25—O81.190 (5)
C13—H13B0.9700C25—O71.363 (5)
C14—O21.190 (5)C25—C261.477 (6)
C14—O11.344 (5)C26—H26A0.9600
C15—H15A0.9600C26—H26B0.9600
C15—H15B0.9600C26—H26C0.9600
O3—C1—C2106.8 (3)H15B—C15—H15C109.5
O3—C1—C7109.6 (2)C12—C16—H16A109.5
C2—C1—C7117.6 (3)C12—C16—H16B109.5
O3—C1—H1107.5H16A—C16—H16B109.5
C2—C1—H1107.5C12—C16—H16C109.5
C7—C1—H1107.5H16A—C16—H16C109.5
C3—C2—C1132.5 (3)H16B—C16—H16C109.5
C3—C2—H2113.7C4—C17—H17A109.5
C1—C2—H2113.7C4—C17—H17B109.5
C2—C3—C4126.5 (3)H17A—C17—H17B109.5
C2—C3—C12117.6 (3)C4—C17—H17C109.5
C4—C3—C12115.8 (3)H17A—C17—H17C109.5
O1—C4—C3107.7 (3)H17B—C17—H17C109.5
O1—C4—C5101.7 (3)O4—C18—O3123.9 (4)
C3—C4—C5113.8 (3)O4—C18—C19124.2 (3)
O1—C4—C17108.6 (3)O3—C18—C19112.0 (3)
C3—C4—C17114.8 (3)C18—C19—H19A109.5
C5—C4—C17109.2 (3)C18—C19—H19B109.5
C6—C5—C4113.3 (3)H19A—C19—H19B109.5
C6—C5—H5A108.9C18—C19—H19C109.5
C4—C5—H5A108.9H19A—C19—H19C109.5
C6—C5—H5B108.9H19B—C19—H19C109.5
C4—C5—H5B108.9C9—C20—C22112.6 (3)
H5A—C5—H5B107.7C9—C20—C21110.5 (3)
C11—C6—C7116.8 (3)C22—C20—C21110.9 (4)
C11—C6—C5122.3 (3)C9—C20—H20107.5
C7—C6—C5120.8 (3)C22—C20—H20107.5
C8—C7—C6120.5 (3)C21—C20—H20107.5
C8—C7—C1119.4 (3)C20—C21—H21A109.5
C6—C7—C1120.2 (3)C20—C21—H21B109.5
C7—C8—C9122.9 (3)H21A—C21—H21B109.5
C7—C8—H8118.5C20—C21—H21C109.5
C9—C8—H8118.5H21A—C21—H21C109.5
C10—C9—C8116.1 (3)H21B—C21—H21C109.5
C10—C9—C20122.6 (3)C20—C22—H22A109.5
C8—C9—C20121.2 (3)C20—C22—H22B109.5
C11—C10—C9121.4 (3)H22A—C22—H22B109.5
C11—C10—O5117.6 (3)C20—C22—H22C109.5
C9—C10—O5121.0 (3)H22A—C22—H22C109.5
C6—C11—C10122.1 (3)H22B—C22—H22C109.5
C6—C11—O7119.4 (3)O6—C23—O5121.9 (4)
C10—C11—O7118.2 (3)O6—C23—C24127.5 (4)
C16—C12—C13107.3 (4)O5—C23—C24110.6 (4)
C16—C12—C15110.7 (5)C23—C24—H24A109.5
C13—C12—C15109.1 (4)C23—C24—H24B109.5
C16—C12—C3109.4 (3)H24A—C24—H24B109.5
C13—C12—C3110.6 (3)C23—C24—H24C109.5
C15—C12—C3109.6 (3)H24A—C24—H24C109.5
C14—C13—C12112.8 (3)H24B—C24—H24C109.5
C14—C13—H13A109.0O8—C25—O7122.9 (4)
C12—C13—H13A109.0O8—C25—C26127.1 (4)
C14—C13—H13B109.0O7—C25—C26110.0 (4)
C12—C13—H13B109.0C25—C26—H26A109.5
H13A—C13—H13B107.8C25—C26—H26B109.5
O2—C14—O1118.7 (4)H26A—C26—H26B109.5
O2—C14—C13125.1 (4)C25—C26—H26C109.5
O1—C14—C13116.2 (3)H26A—C26—H26C109.5
C12—C15—H15A109.5H26B—C26—H26C109.5
C12—C15—H15B109.5C14—O1—C4120.5 (3)
H15A—C15—H15B109.5C18—O3—C1117.0 (3)
C12—C15—H15C109.5C23—O5—C10116.6 (3)
H15A—C15—H15C109.5C25—O7—C11117.0 (3)
O3—C1—C2—C388.4 (4)O5—C10—C11—C6178.8 (3)
C7—C1—C2—C335.3 (5)C9—C10—C11—O7176.5 (3)
C1—C2—C3—C40.6 (6)O5—C10—C11—O74.9 (4)
C1—C2—C3—C12177.2 (4)C2—C3—C12—C1656.6 (5)
C2—C3—C4—O1130.1 (4)C4—C3—C12—C16120.3 (4)
C12—C3—C4—O146.5 (4)C2—C3—C12—C13174.6 (3)
C2—C3—C4—C518.1 (5)C4—C3—C12—C132.3 (5)
C12—C3—C4—C5158.5 (3)C2—C3—C12—C1565.0 (5)
C2—C3—C4—C17108.8 (4)C4—C3—C12—C15118.1 (4)
C12—C3—C4—C1774.6 (4)C16—C12—C13—C1476.1 (5)
O1—C4—C5—C6173.9 (3)C15—C12—C13—C14163.9 (4)
C3—C4—C5—C670.6 (4)C3—C12—C13—C1443.2 (5)
C17—C4—C5—C659.2 (4)C12—C13—C14—O2134.1 (5)
C4—C5—C6—C11105.5 (4)C12—C13—C14—O144.2 (6)
C4—C5—C6—C771.5 (4)C10—C9—C20—C22136.0 (4)
C11—C6—C7—C81.6 (4)C8—C9—C20—C2246.3 (5)
C5—C6—C7—C8178.7 (3)C10—C9—C20—C2199.3 (4)
C11—C6—C7—C1177.2 (3)C8—C9—C20—C2178.3 (4)
C5—C6—C7—C10.1 (4)O2—C14—O1—C4176.2 (4)
O3—C1—C7—C8111.2 (3)C13—C14—O1—C45.4 (6)
C2—C1—C7—C8126.6 (3)C3—C4—O1—C1450.8 (4)
O3—C1—C7—C669.9 (4)C5—C4—O1—C14170.7 (3)
C2—C1—C7—C652.3 (4)C17—C4—O1—C1474.2 (4)
C6—C7—C8—C93.2 (5)O4—C18—O3—C11.8 (5)
C1—C7—C8—C9175.6 (3)C19—C18—O3—C1177.9 (3)
C7—C8—C9—C101.8 (5)C2—C1—O3—C18132.1 (3)
C7—C8—C9—C20176.0 (3)C7—C1—O3—C1899.4 (3)
C8—C9—C10—C111.0 (5)O6—C23—O5—C107.3 (6)
C20—C9—C10—C11178.8 (3)C24—C23—O5—C10170.7 (3)
C8—C9—C10—O5179.6 (3)C11—C10—O5—C2382.3 (4)
C20—C9—C10—O52.6 (5)C9—C10—O5—C2399.0 (4)
C7—C6—C11—C101.1 (5)O8—C25—O7—C110.0 (5)
C5—C6—C11—C10175.9 (3)C26—C25—O7—C11179.7 (3)
C7—C6—C11—O7175.0 (3)C6—C11—O7—C25105.6 (4)
C5—C6—C11—O72.1 (5)C10—C11—O7—C2580.3 (4)
C9—C10—C11—C62.5 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5B···O30.972.493.127 (4)123
C2—H2···O8i0.932.593.288 (5)133
C15—H15A···O2ii0.962.553.490 (6)166
C24—H24B···O4iii0.962.363.304 (6)167
Symmetry codes: (i) x1/2, y+3/2, z+2; (ii) x1/2, y+5/2, z+2; (iii) x+1/2, y+1, z1/2.
 

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