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The title compound, C18H29IO3, features a trans-fused bicyclic system. The carbonyl group lies on the same side as the carbethoxy function and iodine. The six-membered ring has a chair conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804008025/bt6432sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804008025/bt6432Isup2.hkl
Contains datablock I

CCDC reference: 239270

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.040
  • wR factor = 0.107
  • Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.12 Ratio
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.34 Ratio PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C17 PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C17 - C18 ... 1.40 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO & SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO & SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995), PLATON (Spek, 2001).

(I) top
Crystal data top
C18H29IO3F(000) = 856
Mr = 420.31Dx = 1.451 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 13534 reflections
a = 10.9460 (2) Åθ = 3.2–25.4°
b = 15.0522 (3) ŵ = 1.68 mm1
c = 12.8224 (3) ÅT = 291 K
β = 114.4262 (8)°Plate, colourless
V = 1923.54 (7) Å30.50 × 0.22 × 0.08 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
3506 independent reflections
Radiation source: fine-focus sealed tube2004 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
Detector resolution: 19 vertical, 18 horizontal pixels mm-1θmax = 25.4°, θmin = 3.2°
ω scansh = 1313
Absorption correction: multi-scan
SCALEPACK (Otwinowski & Minor, 1997)
k = 1818
Tmin = 0.488, Tmax = 0.878l = 1514
13534 measured reflections
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)] = 0.040H-atom parameters constrained
wR(F2) = 0.107 w = 1/[σ2(Fo2) + (0.0601P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.90(Δ/σ)max < 0.001
3506 reflectionsΔρmax = 0.80 e Å3
200 parametersΔρmin = 0.76 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0029 (5)
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
I10.19241 (3)0.14432 (2)0.28785 (3)0.0894 (2)
O10.5133 (3)0.28194 (17)0.4697 (2)0.0646 (7)
O20.4843 (3)0.48792 (19)0.3278 (3)0.0806 (9)
O30.3158 (3)0.41548 (17)0.3416 (3)0.0739 (8)
C10.4561 (3)0.3320 (2)0.2773 (3)0.0461 (9)
C20.5802 (4)0.3421 (3)0.2515 (3)0.0570 (10)
H2A0.56280.38920.19550.068*
H2B0.59160.28750.21640.068*
C30.7131 (4)0.3629 (3)0.3542 (4)0.0727 (12)
H3A0.71720.42620.36910.087*
H3B0.71340.33280.42120.087*
C40.8369 (5)0.3359 (4)0.3385 (5)0.0957 (17)
H4A0.82620.35310.26230.115*
H4B0.91330.36810.39320.115*
C50.8654 (5)0.2393 (4)0.3535 (5)0.1029 (17)
H5A0.93050.22430.32300.124*
H5B0.78360.20670.30990.124*
C60.9206 (5)0.2097 (4)0.4809 (5)0.1073 (19)
H6A1.01310.22910.51940.129*
H6B0.86970.23960.51700.129*
C70.9149 (5)0.1104 (4)0.4985 (5)0.1050 (18)
H7A0.95740.09810.58000.126*
H7B0.96690.08060.46330.126*
C80.7739 (4)0.0709 (3)0.4499 (4)0.0857 (14)
H8A0.78140.00670.45660.103*
H8B0.73030.08510.36900.103*
C90.6844 (4)0.1031 (3)0.5079 (4)0.0754 (13)
H9A0.70280.06710.57550.090*
H9B0.70850.16390.53310.090*
C100.5351 (4)0.0994 (3)0.4327 (3)0.0630 (11)
H10A0.48630.11020.47970.076*
H10B0.51220.04020.40070.076*
C110.4897 (4)0.1668 (2)0.3349 (3)0.0470 (9)
H11A0.55810.16500.30410.056*
C120.3573 (4)0.1447 (2)0.2342 (4)0.0603 (11)
H12A0.36500.08460.20810.072*
C130.3309 (4)0.2074 (3)0.1352 (3)0.0591 (10)
H13A0.24470.19320.07390.071*
H13B0.39920.19880.10630.071*
C140.3309 (3)0.3045 (3)0.1690 (3)0.0553 (10)
H14A0.25130.31560.18240.066*
H14B0.32570.34170.10550.066*
C150.4864 (3)0.2620 (2)0.3712 (3)0.0463 (9)
C160.4230 (4)0.4206 (3)0.3191 (3)0.0560 (10)
C170.2764 (5)0.4949 (3)0.3834 (4)0.0881 (14)
H17A0.33450.50340.46380.106*
H17B0.28510.54620.34130.106*
C180.1428 (6)0.4864 (5)0.3694 (6)0.154 (3)
H18A0.11670.53900.39730.231*
H18B0.13480.43580.41160.231*
H18C0.08570.47870.28970.231*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0620 (2)0.0940 (3)0.1210 (4)0.00998 (16)0.0466 (2)0.00987 (19)
O10.0872 (19)0.0608 (17)0.0516 (17)0.0044 (14)0.0345 (14)0.0023 (13)
O20.089 (2)0.0527 (17)0.112 (2)0.0127 (16)0.0538 (18)0.0018 (17)
O30.0670 (17)0.0578 (18)0.110 (2)0.0030 (14)0.0492 (16)0.0188 (16)
C10.0456 (19)0.044 (2)0.051 (2)0.0010 (16)0.0224 (17)0.0031 (16)
C20.056 (2)0.060 (2)0.060 (3)0.0022 (18)0.030 (2)0.0119 (18)
C30.051 (2)0.079 (3)0.085 (3)0.003 (2)0.025 (2)0.008 (2)
C40.056 (3)0.127 (5)0.107 (4)0.002 (3)0.036 (3)0.027 (3)
C50.079 (3)0.116 (5)0.132 (5)0.015 (3)0.062 (3)0.012 (4)
C60.060 (3)0.100 (4)0.124 (5)0.008 (3)0.000 (3)0.005 (3)
C70.070 (3)0.101 (4)0.118 (5)0.019 (3)0.012 (3)0.014 (3)
C80.070 (3)0.073 (3)0.102 (4)0.017 (2)0.023 (3)0.003 (3)
C90.082 (3)0.067 (3)0.067 (3)0.016 (2)0.021 (2)0.008 (2)
C100.073 (3)0.050 (2)0.073 (3)0.005 (2)0.037 (2)0.008 (2)
C110.0483 (19)0.045 (2)0.053 (2)0.0041 (16)0.0259 (18)0.0018 (17)
C120.060 (2)0.050 (2)0.076 (3)0.0012 (18)0.033 (2)0.016 (2)
C130.051 (2)0.073 (3)0.049 (2)0.0011 (19)0.0161 (18)0.009 (2)
C140.048 (2)0.062 (3)0.051 (2)0.0050 (18)0.0163 (18)0.0051 (19)
C150.0440 (18)0.050 (2)0.048 (2)0.0029 (16)0.0217 (17)0.0030 (18)
C160.054 (2)0.052 (3)0.055 (2)0.002 (2)0.0166 (19)0.0052 (19)
C170.085 (3)0.076 (3)0.110 (4)0.010 (3)0.047 (3)0.023 (3)
C180.077 (4)0.176 (6)0.201 (7)0.036 (4)0.049 (4)0.074 (6)
Geometric parameters (Å, º) top
I1—C122.182 (4)C7—H7B0.9700
O1—C151.211 (4)C8—C91.533 (6)
O2—C161.195 (4)C8—H8A0.9700
O3—C161.321 (5)C8—H8B0.9700
O3—C171.447 (5)C9—C101.517 (6)
C1—C151.529 (5)C9—H9A0.9700
C1—C21.533 (5)C9—H9B0.9700
C1—C161.535 (5)C10—C111.527 (5)
C1—C141.550 (5)C10—H10A0.9700
C2—C31.537 (6)C10—H10B0.9700
C2—H2A0.9700C11—C151.511 (5)
C2—H2B0.9700C11—C121.526 (5)
C3—C41.506 (7)C11—H11A0.9800
C3—H3A0.9700C12—C131.511 (5)
C3—H3B0.9700C12—H12A0.9800
C4—C51.484 (7)C13—C141.524 (5)
C4—H4A0.9700C13—H13A0.9700
C4—H4B0.9700C13—H13B0.9700
C5—C61.554 (7)C14—H14A0.9700
C5—H5A0.9700C14—H14B0.9700
C5—H5B0.9700C17—C181.403 (7)
C6—C71.517 (7)C17—H17A0.9700
C6—H6A0.9700C17—H17B0.9700
C6—H6B0.9700C18—H18A0.9600
C7—C81.526 (7)C18—H18B0.9600
C7—H7A0.9700C18—H18C0.9600
C16—O3—C17117.5 (3)C10—C9—H9B108.6
C15—C1—C2108.3 (3)C8—C9—H9B108.6
C15—C1—C16109.3 (3)H9A—C9—H9B107.6
C2—C1—C16110.3 (3)C9—C10—C11113.4 (3)
C15—C1—C14110.2 (3)C9—C10—H10A108.9
C2—C1—C14111.5 (3)C11—C10—H10A108.9
C16—C1—C14107.2 (3)C9—C10—H10B108.9
C1—C2—C3116.4 (3)C11—C10—H10B108.9
C1—C2—H2A108.2H10A—C10—H10B107.7
C3—C2—H2A108.2C15—C11—C12109.3 (3)
C1—C2—H2B108.2C15—C11—C10114.7 (3)
C3—C2—H2B108.2C12—C11—C10115.0 (3)
H2A—C2—H2B107.3C15—C11—H11A105.6
C4—C3—C2114.6 (4)C12—C11—H11A105.6
C4—C3—H3A108.6C10—C11—H11A105.6
C2—C3—H3A108.6C13—C12—C11111.1 (3)
C4—C3—H3B108.6C13—C12—I1111.8 (3)
C2—C3—H3B108.6C11—C12—I1110.7 (3)
H3A—C3—H3B107.6C13—C12—H12A107.7
C5—C4—C3113.5 (4)C11—C12—H12A107.7
C5—C4—H4A108.9I1—C12—H12A107.7
C3—C4—H4A108.9C12—C13—C14112.5 (3)
C5—C4—H4B108.9C12—C13—H13A109.1
C3—C4—H4B108.9C14—C13—H13A109.1
H4A—C4—H4B107.7C12—C13—H13B109.1
C4—C5—C6112.8 (5)C14—C13—H13B109.1
C4—C5—H5A109.0H13A—C13—H13B107.8
C6—C5—H5A109.0C13—C14—C1114.0 (3)
C4—C5—H5B109.0C13—C14—H14A108.7
C6—C5—H5B109.0C1—C14—H14A108.7
H5A—C5—H5B107.8C13—C14—H14B108.7
C7—C6—C5114.6 (5)C1—C14—H14B108.7
C7—C6—H6A108.6H14A—C14—H14B107.6
C5—C6—H6A108.6O1—C15—C11122.0 (3)
C7—C6—H6B108.6O1—C15—C1122.0 (3)
C5—C6—H6B108.6C11—C15—C1115.9 (3)
H6A—C6—H6B107.6O2—C16—O3122.9 (4)
C6—C7—C8114.8 (4)O2—C16—C1124.4 (4)
C6—C7—H7A108.6O3—C16—C1112.6 (3)
C8—C7—H7A108.6C18—C17—O3109.4 (4)
C6—C7—H7B108.6C18—C17—H17A109.8
C8—C7—H7B108.6O3—C17—H17A109.8
H7A—C7—H7B107.5C18—C17—H17B109.8
C7—C8—C9114.8 (4)O3—C17—H17B109.8
C7—C8—H8A108.6H17A—C17—H17B108.2
C9—C8—H8A108.6C17—C18—H18A109.5
C7—C8—H8B108.6C17—C18—H18B109.5
C9—C8—H8B108.6H18A—C18—H18B109.5
H8A—C8—H8B107.5C17—C18—H18C109.5
C10—C9—C8114.6 (4)H18A—C18—H18C109.5
C10—C9—H9A108.6H18B—C18—H18C109.5
C8—C9—H9A108.6
C15—C1—C2—C354.5 (4)C2—C1—C14—C1375.0 (4)
C16—C1—C2—C365.1 (4)C16—C1—C14—C13164.1 (3)
C14—C1—C2—C3175.8 (3)C12—C11—C15—O1128.4 (4)
C1—C2—C3—C4156.0 (4)C10—C11—C15—O12.4 (5)
C2—C3—C4—C577.5 (6)C12—C11—C15—C155.5 (4)
C3—C4—C5—C673.6 (6)C10—C11—C15—C1173.7 (3)
C4—C5—C6—C7163.8 (4)C2—C1—C15—O1102.9 (4)
C5—C6—C7—C862.5 (7)C16—C1—C15—O117.4 (4)
C6—C7—C8—C965.5 (6)C14—C1—C15—O1134.9 (3)
C7—C8—C9—C10153.9 (4)C2—C1—C15—C1173.3 (4)
C8—C9—C10—C1169.1 (5)C16—C1—C15—C11166.5 (3)
C9—C10—C11—C1573.3 (4)C14—C1—C15—C1149.0 (4)
C9—C10—C11—C12158.6 (4)C17—O3—C16—O22.9 (6)
C15—C11—C12—C1357.5 (4)C17—O3—C16—C1179.0 (3)
C10—C11—C12—C13171.8 (3)C15—C1—C16—O2120.4 (4)
C15—C11—C12—I167.4 (3)C2—C1—C16—O21.4 (5)
C10—C11—C12—I163.3 (4)C14—C1—C16—O2120.2 (4)
C11—C12—C13—C1456.6 (4)C15—C1—C16—O361.6 (4)
I1—C12—C13—C1467.7 (3)C2—C1—C16—O3179.4 (3)
C12—C13—C14—C150.9 (4)C14—C1—C16—O357.8 (4)
C15—C1—C14—C1345.3 (4)C16—O3—C17—C18162.1 (5)
 

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