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The title compound, C19H19NO5, was synthesized by the reaction of 6-meth­oxy-4-(2-oxo-2-phenyl­ethoxy)-7-methyl­isobenzofuran-3(1H)-one with o-methyl­hydroxy­lamine hydro­chloride in ethanol. It is a new kind of methoxy­imino compound containing isobenzofuran. The dihedral angle between the two six-membered aromatic rings is 104.3 (2)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806054481/om2068sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806054481/om2068Isup2.hkl
Contains datablock I

CCDC reference: 633978

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.045
  • wR factor = 0.144
  • Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for N1 - C12 .. 13.51 su
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - C4 .. 6.53 su
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 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97.

(Z)-6-Methoxy-4-(2-methoxyimino-2-phenylethoxy)-7-methylisobenzofuran-3(1H)-one top
Crystal data top
C19H19NO5F(000) = 720
Mr = 341.35Dx = 1.306 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2369 reflections
a = 9.3964 (2) Åθ = 2.4–23.4°
b = 19.445 (4) ŵ = 0.10 mm1
c = 9.8521 (2) ÅT = 294 K
β = 105.307 (3)°Block, colourless
V = 1736.3 (5) Å30.30 × 0.26 × 0.20 mm
Z = 4
Data collection top
Bruker SMART 1000
diffractometer
3057 independent reflections
Radiation source: fine-focus sealed tube1900 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
φ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1990)
h = 118
Tmin = 0.972, Tmax = 0.981k = 2322
8700 measured reflectionsl = 1111
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0775P)2 + 0.1213P]
where P = (Fo2 + 2Fc2)/3
3057 reflections(Δ/σ)max = 0.001
229 parametersΔρmax = 0.36 e Å3
6 restraintsΔρmin = 0.16 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
O10.4365 (2)0.62799 (9)0.8464 (2)0.0843 (6)
O20.2949 (2)0.59862 (9)0.6357 (2)0.0871 (6)
O30.09117 (16)0.48348 (7)0.67613 (15)0.0528 (4)
O40.12195 (19)0.32628 (9)0.7659 (2)0.0834 (6)
O50.17559 (18)0.43250 (9)1.17123 (16)0.0650 (5)
N10.0025 (2)0.30814 (11)0.7234 (2)0.0682 (6)
C10.3947 (3)0.53375 (15)1.2516 (3)0.0785 (8)
H1A0.48700.55591.25510.118*
H1B0.41290.49131.30320.118*
H1C0.33570.56331.29280.118*
C20.3139 (2)0.51916 (11)1.1004 (3)0.0566 (6)
C30.3427 (2)0.55431 (11)0.9892 (3)0.0552 (6)
C40.4536 (3)0.61048 (12)0.9908 (3)0.0756 (8)
H4A0.43410.65001.04310.091*
H4B0.55300.59431.03360.091*
C50.3270 (3)0.58944 (12)0.7594 (4)0.0670 (7)
C60.2704 (2)0.54224 (10)0.8498 (2)0.0514 (6)
C70.1605 (2)0.49198 (10)0.8147 (2)0.0450 (5)
C80.1292 (2)0.45491 (10)0.9229 (2)0.0468 (5)
H80.05720.42090.90250.056*
C90.2047 (2)0.46810 (11)1.0628 (2)0.0517 (6)
C100.0816 (3)0.37364 (13)1.1389 (3)0.0722 (7)
H10A0.01400.38741.08290.108*
H10B0.07220.35301.22470.108*
H10C0.12350.34091.08760.108*
C110.0159 (2)0.42917 (11)0.6393 (2)0.0549 (6)
H11A0.06760.43300.54040.066*
H11B0.08780.43420.69340.066*
C120.0543 (2)0.35916 (11)0.6667 (2)0.0507 (6)
C130.1922 (3)0.34371 (10)0.6274 (2)0.0498 (6)
C140.2294 (3)0.37777 (12)0.5185 (2)0.0636 (7)
H140.16830.41240.47020.076*
C150.3567 (3)0.36079 (15)0.4808 (3)0.0766 (8)
H150.38010.38360.40660.092*
C160.4485 (3)0.31041 (16)0.5523 (3)0.0810 (8)
H160.53400.29890.52670.097*
C170.4133 (3)0.27688 (13)0.6625 (3)0.0773 (8)
H170.47580.24290.71150.093*
C180.2875 (3)0.29311 (11)0.7002 (3)0.0627 (7)
H180.26530.27030.77490.075*
C190.1645 (4)0.26556 (17)0.8323 (4)0.1122 (12)
H19A0.19270.22960.76380.168*
H19B0.24610.27660.86980.168*
H19C0.08260.25050.90700.168*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0761 (12)0.0576 (11)0.1103 (17)0.0223 (10)0.0087 (11)0.0079 (10)
O20.0885 (14)0.0728 (12)0.0948 (15)0.0149 (10)0.0151 (12)0.0236 (11)
O30.0581 (9)0.0407 (8)0.0541 (10)0.0036 (7)0.0050 (7)0.0020 (7)
O40.0724 (13)0.0670 (11)0.1126 (15)0.0039 (10)0.0274 (11)0.0105 (10)
O50.0686 (11)0.0691 (11)0.0533 (10)0.0049 (9)0.0090 (8)0.0004 (8)
N10.0617 (13)0.0640 (13)0.0750 (14)0.0053 (11)0.0114 (11)0.0037 (11)
C10.0699 (17)0.0809 (18)0.0716 (18)0.0005 (15)0.0044 (14)0.0228 (14)
C20.0470 (13)0.0497 (13)0.0660 (16)0.0056 (11)0.0022 (11)0.0166 (12)
C30.0460 (13)0.0386 (12)0.0753 (17)0.0030 (10)0.0058 (12)0.0117 (11)
C40.0580 (16)0.0490 (14)0.110 (2)0.0073 (12)0.0047 (15)0.0185 (15)
C50.0585 (16)0.0434 (13)0.095 (2)0.0024 (12)0.0136 (15)0.0042 (14)
C60.0477 (13)0.0331 (11)0.0709 (16)0.0019 (10)0.0114 (11)0.0033 (10)
C70.0438 (12)0.0340 (10)0.0542 (14)0.0043 (9)0.0075 (10)0.0026 (10)
C80.0432 (12)0.0410 (11)0.0529 (14)0.0005 (10)0.0068 (10)0.0050 (10)
C90.0490 (13)0.0503 (13)0.0533 (14)0.0066 (11)0.0094 (11)0.0034 (11)
C100.0817 (18)0.0674 (16)0.0654 (16)0.0045 (15)0.0157 (14)0.0072 (13)
C110.0500 (13)0.0515 (13)0.0539 (13)0.0046 (11)0.0028 (11)0.0017 (11)
C120.0587 (14)0.0386 (11)0.0468 (13)0.0100 (11)0.0004 (11)0.0001 (10)
C130.0608 (14)0.0360 (11)0.0462 (13)0.0031 (10)0.0027 (11)0.0062 (10)
C140.0764 (18)0.0591 (14)0.0500 (14)0.0034 (13)0.0071 (13)0.0004 (12)
C150.089 (2)0.0819 (19)0.0601 (17)0.0013 (17)0.0222 (15)0.0085 (14)
C160.0757 (19)0.0829 (19)0.084 (2)0.0055 (17)0.0214 (16)0.0309 (17)
C170.0795 (19)0.0531 (15)0.092 (2)0.0127 (15)0.0101 (16)0.0099 (15)
C180.0718 (17)0.0418 (12)0.0676 (16)0.0005 (12)0.0065 (13)0.0007 (11)
C190.099 (2)0.097 (2)0.149 (3)0.0284 (19)0.049 (2)0.032 (2)
Geometric parameters (Å, º) top
O1—C51.374 (3)C8—C91.397 (3)
O1—C41.430 (3)C8—H80.9300
O2—C51.190 (3)C10—H10A0.9600
O3—C71.359 (2)C10—H10B0.9600
O3—C111.437 (2)C10—H10C0.9600
O4—N11.388 (3)C11—C121.506 (3)
O4—C191.456 (3)C11—H11A0.9700
O5—C91.360 (3)C11—H11B0.9700
O5—C101.429 (3)C12—C131.478 (3)
N1—C121.295 (3)C13—C141.382 (3)
C1—C21.510 (3)C13—C181.395 (3)
C1—H1A0.9600C14—C151.383 (4)
C1—H1B0.9600C14—H140.9300
C1—H1C0.9600C15—C161.371 (4)
C2—C31.378 (3)C15—H150.9300
C2—C91.406 (3)C16—C171.379 (4)
C3—C61.382 (3)C16—H160.9300
C3—C41.507 (3)C17—C181.366 (4)
C4—H4A0.9700C17—H170.9300
C4—H4B0.9700C18—H180.9300
C5—C61.472 (4)C19—H19A0.9600
C6—C71.397 (3)C19—H19B0.9600
C7—C81.382 (3)C19—H19C0.9600
C5—O1—C4111.1 (2)O5—C10—H10B109.5
C7—O3—C11117.48 (16)H10A—C10—H10B109.5
N1—O4—C19106.4 (2)O5—C10—H10C109.5
C9—O5—C10118.25 (17)H10A—C10—H10C109.5
C12—N1—O4112.2 (2)H10B—C10—H10C109.5
C2—C1—H1A109.5O3—C11—C12112.02 (17)
C2—C1—H1B109.5O3—C11—H11A109.2
H1A—C1—H1B109.5C12—C11—H11A109.2
C2—C1—H1C109.5O3—C11—H11B109.2
H1A—C1—H1C109.5C12—C11—H11B109.2
H1B—C1—H1C109.5H11A—C11—H11B107.9
C3—C2—C9115.1 (2)N1—C12—C13114.4 (2)
C3—C2—C1122.6 (2)N1—C12—C11125.0 (2)
C9—C2—C1122.4 (2)C13—C12—C11120.64 (19)
C2—C3—C6123.9 (2)C14—C13—C18118.6 (2)
C2—C3—C4129.2 (2)C14—C13—C12121.6 (2)
C6—C3—C4106.9 (2)C18—C13—C12119.8 (2)
O1—C4—C3105.4 (2)C13—C14—C15120.5 (2)
O1—C4—H4A110.7C13—C14—H14119.7
C3—C4—H4A110.7C15—C14—H14119.7
O1—C4—H4B110.7C16—C15—C14120.3 (3)
C3—C4—H4B110.7C16—C15—H15119.9
H4A—C4—H4B108.8C14—C15—H15119.9
O2—C5—O1120.2 (2)C15—C16—C17119.5 (3)
O2—C5—C6132.7 (2)C15—C16—H16120.2
O1—C5—C6107.1 (2)C17—C16—H16120.2
C3—C6—C7120.1 (2)C18—C17—C16120.6 (3)
C3—C6—C5109.5 (2)C18—C17—H17119.7
C7—C6—C5130.4 (2)C16—C17—H17119.7
O3—C7—C8124.65 (19)C17—C18—C13120.5 (3)
O3—C7—C6117.43 (19)C17—C18—H18119.8
C8—C7—C6117.9 (2)C13—C18—H18119.8
C7—C8—C9120.6 (2)O4—C19—H19A109.5
C7—C8—H8119.7O4—C19—H19B109.5
C9—C8—H8119.7H19A—C19—H19B109.5
O5—C9—C8121.8 (2)O4—C19—H19C109.5
O5—C9—C2115.9 (2)H19A—C19—H19C109.5
C8—C9—C2122.3 (2)H19B—C19—H19C109.5
O5—C10—H10A109.5
C19—O4—N1—C12177.7 (2)C10—O5—C9—C89.5 (3)
C9—C2—C3—C60.8 (3)C10—O5—C9—C2171.1 (2)
C1—C2—C3—C6179.9 (2)C7—C8—C9—O5179.78 (19)
C9—C2—C3—C4178.5 (2)C7—C8—C9—C20.4 (3)
C1—C2—C3—C40.8 (4)C3—C2—C9—O5179.52 (19)
C5—O1—C4—C30.8 (3)C1—C2—C9—O50.2 (3)
C2—C3—C4—O1179.8 (2)C3—C2—C9—C81.1 (3)
C6—C3—C4—O10.4 (2)C1—C2—C9—C8179.6 (2)
C4—O1—C5—O2177.9 (2)C7—O3—C11—C1267.5 (2)
C4—O1—C5—C61.6 (3)O4—N1—C12—C13176.46 (16)
C2—C3—C6—C70.2 (3)O4—N1—C12—C114.1 (3)
C4—C3—C6—C7179.65 (19)O3—C11—C12—N1137.1 (2)
C2—C3—C6—C5179.2 (2)O3—C11—C12—C1343.5 (3)
C4—C3—C6—C51.3 (2)N1—C12—C13—C14152.3 (2)
O2—C5—C6—C3177.6 (3)C11—C12—C13—C1427.2 (3)
O1—C5—C6—C31.8 (2)N1—C12—C13—C1827.0 (3)
O2—C5—C6—C71.3 (5)C11—C12—C13—C18153.50 (19)
O1—C5—C6—C7179.3 (2)C18—C13—C14—C151.5 (3)
C11—O3—C7—C84.1 (3)C12—C13—C14—C15177.9 (2)
C11—O3—C7—C6176.50 (18)C13—C14—C15—C160.8 (4)
C3—C6—C7—O3178.59 (18)C14—C15—C16—C170.2 (4)
C5—C6—C7—O30.2 (3)C15—C16—C17—C180.4 (4)
C3—C6—C7—C80.9 (3)C16—C17—C18—C130.3 (4)
C5—C6—C7—C8179.7 (2)C14—C13—C18—C171.2 (3)
O3—C7—C8—C9178.85 (18)C12—C13—C18—C17178.1 (2)
C6—C7—C8—C90.6 (3)
 

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