Download citation
Download citation
link to html
In the title compound, C17H18O4, the heterocyclic ring has a half-chair conformation. The substituents at the 3- and 4-positions are attached equatorially with respect to the heterocyclic ring. The mol­ecules are linked by O—H...O hydrogen bonds, the hydroxyl O atom functioning as both donor and acceptor. This results in the formation of C(2) chains running along the twofold screw axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803026102/wn6195sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803026102/wn6195Isup2.hkl
Contains datablock I

CCDC reference: 227909

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.069
  • wR factor = 0.185
  • Data-to-parameter ratio = 7.2

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing .. ?
Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.19 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.16 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
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 67.49 From the CIF: _reflns_number_total 1388 Count of symmetry unique reflns 1430 Completeness (_total/calc) 97.06% 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
2 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 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: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1989); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PARST97 (Nardelli, 1996).

8-Methoxy-4-(4-methoxyphenyl)isochroman-3-ol top
Crystal data top
C17H18O4F(000) = 304
Mr = 286.31Dx = 1.342 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ybCell parameters from 45 reflections
a = 10.5330 (18) Åθ = 45.6–57.4°
b = 5.145 (3) ŵ = 0.78 mm1
c = 13.607 (3) ÅT = 293 K
β = 106.018 (15)°Prism, colourless
V = 708.8 (5) Å30.5 × 0.3 × 0.3 mm
Z = 2
Data collection top
Rigaku AFC-5S
diffractometer
Rint = 0.061
Graphite monochromatorθmax = 67.5°, θmin = 3.4°
ω scansh = 1212
Absorption correction: ψ scan
(North et al., 1968)
k = 66
Tmin = 0.750, Tmax = 0.793l = 1616
4913 measured reflections3 standard reflections every 150 reflections
1388 independent reflections intensity decay: <2%
1262 reflections with I > 2σ(I)
Refinement top
Refinement on F21 restraint
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.069 w = 1/[σ2(Fo2) + (0.153P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.185(Δ/σ)max < 0.001
S = 1.09Δρmax = 0.53 e Å3
1388 reflectionsΔρmin = 0.24 e Å3
193 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O20.1709 (2)0.0865 (6)0.16822 (19)0.0420 (7)
O310.0210 (3)0.0785 (5)0.04204 (19)0.0431 (6)
H310.00950.22190.01960.065*
O80.3652 (2)0.0746 (7)0.4743 (2)0.0538 (8)
C30.0321 (3)0.0764 (8)0.1480 (2)0.0349 (8)
H30.00050.22750.17830.042*
C40.0086 (3)0.1743 (8)0.1915 (3)0.0368 (8)
H40.01460.31990.15330.044*
C60.1064 (4)0.4100 (10)0.4671 (3)0.0506 (10)
H60.08080.53110.50860.061*
C100.0719 (3)0.2027 (7)0.3033 (3)0.0378 (8)
C90.1863 (3)0.0577 (8)0.3409 (3)0.0410 (8)
O440.5596 (3)0.2056 (8)0.1545 (3)0.0630 (10)
C10.2349 (3)0.1223 (10)0.2735 (3)0.0471 (10)
H1A0.32910.09620.2850.057*
H1B0.22140.30.29220.057*
C440.4284 (4)0.2087 (9)0.1566 (3)0.0456 (10)
C80.2574 (3)0.0815 (9)0.4439 (3)0.0445 (9)
C50.0328 (4)0.3799 (9)0.3672 (3)0.0458 (9)
H50.04340.47810.3420.055*
C800.4370 (5)0.0733 (14)0.5805 (4)0.0705 (15)
H80A0.47820.09310.59820.106*
H80B0.50360.20620.59320.106*
H80C0.37740.1060.62120.106*
C410.1573 (3)0.1843 (7)0.1770 (3)0.0374 (8)
C450.3523 (4)0.0236 (10)0.2173 (3)0.0491 (10)
H450.39150.09670.25080.059*
C460.2172 (4)0.0132 (10)0.2295 (3)0.0466 (10)
H460.16620.10960.27320.056*
C420.2355 (4)0.3688 (10)0.1138 (3)0.0475 (10)
H420.19680.48370.07790.057*
C4400.6421 (4)0.4063 (12)0.1003 (4)0.0643 (13)
H44A0.6040.57210.1240.096*
H44B0.72780.39320.11170.096*
H44C0.65030.38940.02850.096*
C430.3715 (4)0.3857 (9)0.1029 (3)0.0484 (10)
H430.42280.51150.06110.058*
C70.2192 (4)0.2600 (11)0.5066 (3)0.0526 (10)
H70.26850.27950.57430.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0341 (11)0.0524 (17)0.0417 (13)0.0011 (12)0.0144 (9)0.0032 (12)
O310.0476 (13)0.0462 (15)0.0341 (12)0.0033 (13)0.0091 (10)0.0031 (11)
O80.0424 (13)0.069 (2)0.0441 (15)0.0065 (14)0.0014 (11)0.0049 (14)
C30.0325 (15)0.0373 (19)0.0342 (16)0.0038 (15)0.0082 (12)0.0000 (15)
C40.0348 (16)0.041 (2)0.0347 (16)0.0014 (15)0.0091 (12)0.0027 (15)
C60.056 (2)0.050 (2)0.047 (2)0.005 (2)0.0165 (17)0.0135 (19)
C100.0334 (15)0.040 (2)0.0398 (19)0.0037 (15)0.0101 (14)0.0000 (15)
C90.0354 (15)0.045 (2)0.0451 (19)0.0017 (15)0.0147 (14)0.0005 (16)
O440.0343 (13)0.079 (2)0.078 (2)0.0041 (16)0.0183 (13)0.0128 (19)
C10.0337 (16)0.063 (3)0.0428 (19)0.0062 (18)0.0078 (14)0.0046 (19)
C440.0343 (16)0.051 (2)0.052 (2)0.0023 (17)0.0129 (15)0.0011 (18)
C80.0334 (16)0.052 (2)0.047 (2)0.0006 (18)0.0100 (14)0.0003 (18)
C50.0440 (17)0.049 (2)0.046 (2)0.0054 (18)0.0160 (15)0.0009 (18)
C800.058 (2)0.096 (4)0.048 (2)0.014 (3)0.001 (2)0.001 (3)
C410.0350 (16)0.040 (2)0.0362 (16)0.0027 (16)0.0091 (13)0.0012 (15)
C450.0425 (19)0.057 (3)0.052 (2)0.0013 (18)0.0193 (17)0.0074 (19)
C460.0383 (17)0.054 (2)0.049 (2)0.0053 (17)0.0147 (15)0.0079 (18)
C420.0373 (16)0.058 (3)0.0465 (19)0.0033 (18)0.0107 (14)0.0107 (19)
C4400.0359 (17)0.072 (3)0.083 (3)0.010 (2)0.0124 (19)0.004 (3)
C430.0368 (17)0.051 (2)0.052 (2)0.0057 (17)0.0045 (15)0.0107 (19)
C70.051 (2)0.065 (3)0.0384 (19)0.001 (2)0.0078 (16)0.0112 (19)
Geometric parameters (Å, º) top
O2—C31.413 (4)C1—H1B0.97
O2—C11.417 (4)C44—C451.366 (6)
O31—C31.396 (4)C44—C431.402 (6)
O31—H310.82C8—C71.386 (6)
O8—C81.359 (5)C5—H50.93
O8—C801.435 (5)C80—H80A0.96
C3—C41.528 (5)C80—H80B0.96
C3—H30.98C80—H80C0.96
C4—C411.525 (4)C41—C421.389 (6)
C4—C101.531 (5)C41—C461.389 (6)
C4—H40.98C45—C461.388 (5)
C6—C51.376 (5)C45—H450.93
C6—C71.394 (6)C46—H460.93
C6—H60.93C42—C431.402 (5)
C10—C91.389 (5)C42—H420.93
C10—C51.398 (5)C440—H44A0.96
C9—C81.400 (5)C440—H44B0.96
C9—C11.489 (6)C440—H44C0.96
O44—C441.374 (4)C43—H430.93
O44—C4401.418 (6)C7—H70.93
C1—H1A0.97
C3—O2—C1112.3 (2)O8—C8—C9115.0 (3)
C3—O31—H31109.5C7—C8—C9120.6 (4)
C8—O8—C80117.9 (3)C6—C5—C10120.4 (4)
O31—C3—O2107.4 (3)C6—C5—H5119.8
O31—C3—C4109.3 (3)C10—C5—H5119.8
O2—C3—C4109.9 (3)O8—C80—H80A109.5
O31—C3—H3110O8—C80—H80B109.5
O2—C3—H3110H80A—C80—H80B109.5
C4—C3—H3110O8—C80—H80C109.5
C41—C4—C3111.5 (3)H80A—C80—H80C109.5
C41—C4—C10113.1 (3)H80B—C80—H80C109.5
C3—C4—C10109.1 (3)C42—C41—C46118.4 (3)
C41—C4—H4107.6C42—C41—C4121.0 (3)
C3—C4—H4107.6C46—C41—C4120.5 (3)
C10—C4—H4107.6C44—C45—C46120.7 (4)
C5—C6—C7120.4 (4)C44—C45—H45119.7
C5—C6—H6119.8C46—C45—H45119.7
C7—C6—H6119.8C45—C46—C41120.7 (4)
C9—C10—C5119.7 (3)C45—C46—H46119.7
C9—C10—C4120.1 (3)C41—C46—H46119.7
C5—C10—C4120.2 (3)C41—C42—C43121.4 (4)
C10—C9—C8119.4 (3)C41—C42—H42119.3
C10—C9—C1121.2 (3)C43—C42—H42119.3
C8—C9—C1119.4 (3)O44—C440—H44A109.5
C44—O44—C440118.1 (4)O44—C440—H44B109.5
O2—C1—C9113.2 (3)H44A—C440—H44B109.5
O2—C1—H1A108.9O44—C440—H44C109.5
C9—C1—H1A108.9H44A—C440—H44C109.5
O2—C1—H1B108.9H44B—C440—H44C109.5
C9—C1—H1B108.9C42—C43—C44118.4 (4)
H1A—C1—H1B107.8C42—C43—H43120.8
C45—C44—O44115.1 (4)C44—C43—H43120.8
C45—C44—C43120.3 (3)C8—C7—C6119.4 (4)
O44—C44—C43124.6 (4)C8—C7—H7120.3
O8—C8—C7124.4 (4)C6—C7—H7120.3
C1—O2—C3—O31171.7 (3)C10—C9—C8—C74.1 (6)
C1—O2—C3—C469.5 (4)C1—C9—C8—C7175.7 (4)
O31—C3—C4—C4165.9 (4)C7—C6—C5—C101.5 (7)
O2—C3—C4—C41176.4 (3)C9—C10—C5—C60.4 (6)
O31—C3—C4—C10168.4 (3)C4—C10—C5—C6178.7 (4)
O2—C3—C4—C1050.8 (4)C3—C4—C41—C42114.4 (4)
C41—C4—C10—C9141.7 (4)C10—C4—C41—C42122.2 (4)
C3—C4—C10—C917.0 (4)C3—C4—C41—C4667.5 (4)
C41—C4—C10—C540.1 (5)C10—C4—C41—C4655.9 (5)
C3—C4—C10—C5164.8 (3)O44—C44—C45—C46177.2 (4)
C5—C10—C9—C83.2 (5)C43—C44—C45—C462.2 (7)
C4—C10—C9—C8178.6 (3)C44—C45—C46—C412.6 (7)
C5—C10—C9—C1176.6 (4)C42—C41—C46—C451.2 (6)
C4—C10—C9—C11.6 (6)C4—C41—C46—C45179.3 (4)
C3—O2—C1—C948.4 (4)C46—C41—C42—C430.5 (6)
C10—C9—C1—O212.6 (5)C4—C41—C42—C43177.6 (4)
C8—C9—C1—O2167.3 (3)C41—C42—C43—C440.9 (7)
C440—O44—C44—C45174.6 (4)C45—C44—C43—C420.5 (6)
C440—O44—C44—C434.8 (6)O44—C44—C43—C42178.9 (4)
C80—O8—C8—C76.4 (6)O8—C8—C7—C6180.0 (5)
C80—O8—C8—C9175.7 (4)C9—C8—C7—C62.2 (7)
C10—C9—C8—O8177.9 (4)C5—C6—C7—C80.6 (7)
C1—C9—C8—O82.3 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O31—H31···O31i0.822.082.899 (4)178
Symmetry code: (i) x, y1/2, z.
 

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