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The title compound, C17H27O7P, is an important intermediate in the synthesis of an oxy­gen analogue of the michell­amines, which are bisbi­aryl naphthyl­iso­quinoline alkaloids with anti-HIV activities. The crystal structure of the title compound confirms the relative trans stereochemistry of the methyl substituents in the heterocycle, as well as the position of the phosphate ester at the C-5 atom of the isochromane system.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802004567/ya6095sup1.cif
Contains datablocks global, 6

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802004567/ya60956sup2.hkl
Contains datablock 6

CCDC reference: 183807

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.074
  • wR factor = 0.170
  • Data-to-parameter ratio = 17.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
ABSMU_01 Alert C The ratio of given/expected absorption coefficient lies outside the range 0.99 <> 1.01 Calculated value of mu = 0.176 Value of mu given = 0.180
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: SMART-NT (Bruker 1998); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 1999); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 1990); software used to prepare material for publication: SHELXTL.

6,8-Dimethoxy-1,3-trans-dimethylisochroman-5-yl diethyl phosphate top
Crystal data top
C17H27O7PF(000) = 1600
Mr = 374.36Dx = 1.286 Mg m3
Monoclinic, C2/cMelting point: 348 K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 19.7987 (11) ÅCell parameters from 1024 reflections
b = 11.2320 (5) Åθ = 2.1–27.0°
c = 19.3329 (11) ŵ = 0.18 mm1
β = 115.880 (2)°T = 296 K
V = 3868.1 (4) Å3Needle, colourless
Z = 80.40 × 0.08 × 0.08 mm
Data collection top
Bruker SMART 1K CCD
diffractometer
4155 independent reflections
Radiation source: fine-focus sealed tube2976 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
ω scansθmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2425
Tmin = 0.933, Tmax = 0.986k = 1114
11051 measured reflectionsl = 2422
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.074 w = 1/[σ2(Fo2) + (0.0544P)2 + 5.2563P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.170(Δ/σ)max < 0.001
S = 1.15Δρmax = 0.55 e Å3
4155 reflectionsΔρmin = 0.25 e Å3
232 parameters
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
P10.14471 (4)0.35847 (7)0.15345 (5)0.0420 (2)
C10.0019 (2)0.8164 (3)0.1294 (2)0.0580 (9)
H10.00470.84670.17810.070*
O20.07307 (14)0.8424 (2)0.12900 (15)0.0629 (7)
C30.0848 (2)0.7821 (3)0.0710 (2)0.0570 (9)
H30.04180.79690.02130.068*
C40.09110 (18)0.6503 (3)0.08651 (19)0.0482 (7)
H4A0.08700.60870.04090.058*
H4B0.14020.63310.12760.058*
C4A0.03190 (16)0.6043 (3)0.10861 (16)0.0401 (7)
C50.02111 (16)0.4825 (3)0.11243 (16)0.0404 (7)
C60.03192 (16)0.4375 (3)0.13388 (17)0.0431 (7)
C70.07500 (16)0.5155 (3)0.15376 (17)0.0462 (7)
H70.11060.48680.16880.055*
C80.06410 (18)0.6369 (3)0.15075 (18)0.0473 (7)
C8A0.01116 (17)0.6829 (3)0.12856 (17)0.0453 (7)
C90.0609 (2)0.8817 (4)0.0664 (3)0.0847 (13)
H9A0.05070.96560.07160.127*
H9B0.10710.86620.06970.127*
H9C0.06520.85510.01740.127*
C100.1539 (3)0.8346 (4)0.0693 (3)0.0790 (12)
H10A0.14560.91750.05610.119*
H10B0.16470.79360.03170.119*
H10C0.19560.82630.11900.119*
O110.06392 (11)0.40114 (18)0.09216 (11)0.0436 (5)
O120.16169 (12)0.3888 (2)0.23232 (12)0.0528 (6)
O130.20135 (11)0.4137 (2)0.12625 (12)0.0498 (5)
C140.1954 (2)0.3978 (4)0.0495 (2)0.0643 (10)
H14A0.14360.40670.01180.077*
H14B0.21230.31870.04420.077*
C150.2433 (2)0.4898 (4)0.0369 (3)0.0884 (14)
H15A0.22390.56760.03860.133*
H15B0.24300.47760.01230.133*
H15C0.29380.48340.07650.133*
O160.14601 (13)0.22405 (19)0.13352 (13)0.0557 (6)
C170.1117 (2)0.1345 (3)0.1626 (2)0.0599 (9)
H17A0.08820.07370.12370.072*
H17B0.07290.17130.17330.072*
C180.1684 (3)0.0786 (4)0.2337 (2)0.0819 (13)
H18A0.20610.04040.22280.123*
H18B0.14450.02060.25200.123*
H18C0.19140.13860.27220.123*
O190.03771 (13)0.31574 (19)0.13397 (14)0.0571 (6)
C200.0928 (2)0.2657 (3)0.1537 (3)0.0728 (11)
H20A0.08360.29110.20450.109*
H20B0.09020.18050.15250.109*
H20C0.14170.29180.11760.109*
O210.10346 (14)0.7204 (2)0.17059 (15)0.0642 (7)
C220.1588 (2)0.6797 (4)0.1933 (2)0.0631 (10)
H22A0.19850.64070.15080.095*
H22B0.17900.74630.20940.095*
H22C0.13640.62470.23530.095*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0448 (4)0.0363 (4)0.0455 (4)0.0036 (3)0.0205 (3)0.0001 (3)
C10.066 (2)0.0428 (18)0.077 (2)0.0066 (16)0.0412 (19)0.0026 (17)
O20.0706 (16)0.0466 (14)0.0780 (17)0.0038 (12)0.0383 (14)0.0031 (12)
C30.066 (2)0.0455 (19)0.065 (2)0.0006 (16)0.0338 (18)0.0059 (16)
C40.0543 (19)0.0444 (18)0.0497 (18)0.0027 (15)0.0263 (15)0.0004 (14)
C4A0.0412 (16)0.0403 (16)0.0385 (16)0.0008 (13)0.0172 (13)0.0018 (12)
C50.0381 (15)0.0410 (17)0.0413 (16)0.0031 (13)0.0165 (13)0.0030 (13)
C60.0429 (17)0.0405 (17)0.0449 (17)0.0011 (13)0.0182 (14)0.0039 (13)
C70.0368 (16)0.055 (2)0.0474 (17)0.0036 (14)0.0193 (14)0.0058 (15)
C80.0495 (18)0.0474 (18)0.0466 (17)0.0111 (15)0.0224 (14)0.0051 (15)
C8A0.0475 (17)0.0428 (17)0.0472 (17)0.0038 (14)0.0220 (14)0.0014 (14)
C90.080 (3)0.063 (3)0.107 (3)0.020 (2)0.037 (3)0.023 (2)
C100.100 (3)0.058 (2)0.107 (3)0.007 (2)0.071 (3)0.007 (2)
O110.0449 (12)0.0416 (11)0.0460 (12)0.0029 (9)0.0214 (10)0.0042 (9)
O120.0584 (14)0.0543 (14)0.0452 (12)0.0063 (11)0.0221 (11)0.0004 (10)
O130.0455 (12)0.0544 (13)0.0520 (13)0.0007 (10)0.0236 (10)0.0003 (10)
C140.068 (2)0.077 (3)0.060 (2)0.000 (2)0.0386 (19)0.0013 (19)
C150.075 (3)0.117 (4)0.090 (3)0.011 (3)0.052 (3)0.010 (3)
O160.0686 (15)0.0377 (12)0.0679 (15)0.0083 (11)0.0362 (12)0.0000 (11)
C170.066 (2)0.0392 (18)0.074 (2)0.0018 (16)0.0307 (19)0.0025 (17)
C180.098 (3)0.062 (3)0.078 (3)0.012 (2)0.031 (3)0.017 (2)
O190.0655 (15)0.0423 (12)0.0773 (16)0.0039 (11)0.0439 (13)0.0001 (11)
C200.088 (3)0.055 (2)0.099 (3)0.014 (2)0.063 (3)0.002 (2)
O210.0689 (16)0.0550 (15)0.0873 (18)0.0161 (12)0.0514 (14)0.0063 (13)
C220.057 (2)0.074 (2)0.067 (2)0.0153 (19)0.0351 (19)0.0045 (19)
Geometric parameters (Å, º) top
P1—O121.451 (2)C9—H9C0.9600
P1—O131.560 (2)C10—H10A0.9600
P1—O161.561 (2)C10—H10B0.9600
P1—O111.593 (2)C10—H10C0.9600
C1—O21.442 (4)O13—C141.448 (4)
C1—C91.499 (5)C14—C151.493 (5)
C1—C8A1.521 (5)C14—H14A0.9700
C1—H10.9800C14—H14B0.9700
O2—C31.413 (4)C15—H15A0.9600
C3—C101.503 (5)C15—H15B0.9600
C3—C41.505 (4)C15—H15C0.9600
C3—H30.9800O16—C171.457 (4)
C4—C4A1.503 (4)C17—C181.482 (5)
C4—H4A0.9700C17—H17A0.9700
C4—H4B0.9700C17—H17B0.9700
C4A—C51.392 (4)C18—H18A0.9600
C4A—C8A1.394 (4)C18—H18B0.9600
C5—C61.382 (4)C18—H18C0.9600
C5—O111.413 (3)O19—C201.418 (4)
C6—O191.373 (4)C20—H20A0.9600
C6—C71.389 (4)C20—H20B0.9600
C7—C81.385 (4)C20—H20C0.9600
C7—H70.9300O21—C221.423 (4)
C8—O211.377 (4)C22—H22A0.9600
C8—C8A1.394 (4)C22—H22B0.9600
C9—H9A0.9600C22—H22C0.9600
C9—H9B0.9600
O12—P1—O13112.94 (13)H9B—C9—H9C109.5
O12—P1—O16117.72 (13)C3—C10—H10A109.5
O13—P1—O16102.10 (13)C3—C10—H10B109.5
O12—P1—O11114.07 (12)H10A—C10—H10B109.5
O13—P1—O11105.41 (12)C3—C10—H10C109.5
O16—P1—O11103.11 (12)H10A—C10—H10C109.5
O2—C1—C9111.3 (3)H10B—C10—H10C109.5
O2—C1—C8A111.2 (3)C5—O11—P1121.15 (18)
C9—C1—C8A113.4 (3)C14—O13—P1123.2 (2)
O2—C1—H1106.8O13—C14—C15107.9 (3)
C9—C1—H1106.8O13—C14—H14A110.1
C8A—C1—H1106.8C15—C14—H14A110.1
C3—O2—C1113.9 (3)O13—C14—H14B110.1
O2—C3—C10107.2 (3)C15—C14—H14B110.1
O2—C3—C4110.0 (3)H14A—C14—H14B108.4
C10—C3—C4113.1 (3)C14—C15—H15A109.5
O2—C3—H3108.8C14—C15—H15B109.5
C10—C3—H3108.8H15A—C15—H15B109.5
C4—C3—H3108.8C14—C15—H15C109.5
C4A—C4—C3112.8 (3)H15A—C15—H15C109.5
C4A—C4—H4A109.0H15B—C15—H15C109.5
C3—C4—H4A109.0C17—O16—P1120.8 (2)
C4A—C4—H4B109.0O16—C17—C18110.9 (3)
C3—C4—H4B109.0O16—C17—H17A109.5
H4A—C4—H4B107.8C18—C17—H17A109.5
C5—C4A—C8A118.8 (3)O16—C17—H17B109.5
C5—C4A—C4120.7 (3)C18—C17—H17B109.5
C8A—C4A—C4120.5 (3)H17A—C17—H17B108.0
C6—C5—C4A122.0 (3)C17—C18—H18A109.5
C6—C5—O11118.3 (3)C17—C18—H18B109.5
C4A—C5—O11119.7 (3)H18A—C18—H18B109.5
O19—C6—C5116.0 (3)C17—C18—H18C109.5
O19—C6—C7124.5 (3)H18A—C18—H18C109.5
C5—C6—C7119.5 (3)H18B—C18—H18C109.5
C8—C7—C6118.9 (3)C6—O19—C20118.0 (3)
C8—C7—H7120.6O19—C20—H20A109.5
C6—C7—H7120.6O19—C20—H20B109.5
O21—C8—C7122.8 (3)H20A—C20—H20B109.5
O21—C8—C8A115.2 (3)O19—C20—H20C109.5
C7—C8—C8A122.0 (3)H20A—C20—H20C109.5
C4A—C8A—C8118.9 (3)H20B—C20—H20C109.5
C4A—C8A—C1120.4 (3)C8—O21—C22118.2 (3)
C8—C8A—C1120.7 (3)O21—C22—H22A109.5
C1—C9—H9A109.5O21—C22—H22B109.5
C1—C9—H9B109.5H22A—C22—H22B109.5
H9A—C9—H9B109.5O21—C22—H22C109.5
C1—C9—H9C109.5H22A—C22—H22C109.5
H9A—C9—H9C109.5H22B—C22—H22C109.5
C9—C1—O2—C376.9 (4)C7—C8—C8A—C4A0.2 (5)
C8A—C1—O2—C350.5 (4)O21—C8—C8A—C11.7 (4)
C1—O2—C3—C10170.2 (3)C7—C8—C8A—C1177.2 (3)
C1—O2—C3—C466.5 (4)O2—C1—C8A—C4A16.0 (4)
O2—C3—C4—C4A45.1 (4)C9—C1—C8A—C4A110.3 (4)
C10—C3—C4—C4A164.9 (3)O2—C1—C8A—C8161.4 (3)
C3—C4—C4A—C5169.1 (3)C9—C1—C8A—C872.3 (4)
C3—C4—C4A—C8A13.4 (4)C6—C5—O11—P195.3 (3)
C8A—C4A—C5—C61.3 (4)C4A—C5—O11—P186.2 (3)
C4—C4A—C5—C6178.8 (3)O12—P1—O11—C512.7 (3)
C8A—C4A—C5—O11179.7 (2)O13—P1—O11—C5111.7 (2)
C4—C4A—C5—O112.8 (4)O16—P1—O11—C5141.6 (2)
C4A—C5—C6—O19178.9 (3)O12—P1—O13—C14178.9 (2)
O11—C5—C6—O190.5 (4)O16—P1—O13—C1453.7 (3)
C4A—C5—C6—C71.3 (4)O11—P1—O13—C1453.8 (3)
O11—C5—C6—C7179.7 (3)P1—O13—C14—C15163.4 (3)
O19—C6—C7—C8179.5 (3)O12—P1—O16—C1743.9 (3)
C5—C6—C7—C80.7 (4)O13—P1—O16—C17168.2 (2)
C6—C7—C8—O21179.0 (3)O11—P1—O16—C1782.6 (2)
C6—C7—C8—C8A0.2 (5)P1—O16—C17—C1896.1 (3)
C5—C4A—C8A—C80.8 (4)C5—C6—O19—C20178.4 (3)
C4—C4A—C8A—C8178.3 (3)C7—C6—O19—C201.8 (5)
C5—C4A—C8A—C1176.6 (3)C7—C8—O21—C221.5 (5)
C4—C4A—C8A—C10.9 (5)C8A—C8—O21—C22179.6 (3)
O21—C8—C8A—C4A179.1 (3)
 

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