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The mol­ecule of the title compound, C14H14O4, is planar and the structural dimensions are in the normal ranges. There are two intramolecular O—H...O hydrogen bonds, but no intermolecular interactions were observed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804030181/sj6028sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804030181/sj6028Isup2.hkl
Contains datablock I

CCDC reference: 262448

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.066
  • wR factor = 0.148
  • Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ... 567.70 Ang-3 PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ...... C11 PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ...... C14
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

1-(1,8-Dihydroxy-6-methoxy-3-methylnaphthalen-2-yl)ethanone top
Crystal data top
C14H14O4Z = 2
Mr = 246.25F(000) = 260
Triclinic, P1Dx = 1.441 Mg m3
a = 6.993 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.543 (4) ÅCell parameters from 518 reflections
c = 11.058 (6) Åθ = 1.8–25.0°
α = 83.530 (9)°µ = 0.11 mm1
β = 85.171 (9)°T = 273 K
γ = 79.017 (9)°Slab, yellow
V = 567.7 (5) Å30.50 × 0.18 × 0.16 mm
Data collection top
Bruker SMART APEX area-detector
diffractometer
1981 independent reflections
Radiation source: fine-focus sealed tube1368 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
Detector resolution: 83.66 pixels mm-1θmax = 25.0°, θmin = 1.8°
ω scansh = 88
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 88
Tmin = 0.94, Tmax = 0.98l = 1313
5437 measured reflections
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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148H-atom parameters constrained
S = 1.14 w = 1/[σ2(Fo2) + (0.05P)2 + 0.2434P]
where P = (Fo2 + 2Fc2)/3
1981 reflections(Δ/σ)max < 0.001
163 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.14 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.3227 (3)0.7118 (3)0.58026 (17)0.0539 (6)
O20.3927 (3)0.1637 (2)0.82437 (17)0.0511 (6)
H2A0.38560.11930.89540.077*
O30.3292 (3)0.1679 (2)1.05644 (16)0.0453 (5)
H3A0.31640.12801.12820.068*
O40.2702 (3)0.1624 (3)1.27364 (18)0.0533 (6)
C10.1800 (4)0.6392 (3)1.1342 (2)0.0353 (7)
C20.1907 (4)0.7227 (3)1.0196 (3)0.0385 (7)
H2B0.16000.84881.00990.046*
C30.2456 (4)0.6311 (3)0.9134 (2)0.0336 (7)
C40.2545 (4)0.7267 (4)0.7971 (2)0.0400 (7)
H4A0.22350.85280.78820.048*
C50.3092 (4)0.6330 (4)0.6972 (3)0.0420 (7)
C60.3552 (4)0.4441 (4)0.7086 (2)0.0429 (7)
H6A0.39180.38330.63930.052*
C70.3472 (4)0.3471 (3)0.8204 (2)0.0353 (7)
C80.2919 (4)0.4382 (3)0.9273 (2)0.0334 (6)
C90.2825 (4)0.3488 (3)1.0469 (2)0.0350 (7)
C100.2268 (4)0.4420 (3)1.1518 (2)0.0331 (6)
C110.1199 (4)0.7595 (4)1.2361 (3)0.0482 (8)
H11A0.09650.88431.20280.072*
H11B0.22210.74021.29150.072*
H11C0.00270.73071.27890.072*
C120.2712 (5)0.9049 (4)0.5610 (3)0.0680 (10)
H12A0.28690.94310.47550.102*
H12B0.35440.95880.60490.102*
H12C0.13780.94270.58960.102*
C130.2231 (4)0.3326 (4)1.2684 (2)0.0392 (7)
C140.1659 (5)0.4031 (4)1.3890 (3)0.0541 (9)
H14A0.17570.30361.45180.081*
H14B0.03380.46831.38930.081*
H14C0.25120.48311.40370.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0713 (15)0.0507 (13)0.0368 (12)0.0089 (11)0.0078 (10)0.0072 (9)
O20.0791 (16)0.0326 (11)0.0408 (12)0.0031 (10)0.0094 (11)0.0083 (9)
O30.0676 (14)0.0290 (10)0.0371 (11)0.0065 (9)0.0011 (10)0.0004 (8)
O40.0723 (15)0.0382 (12)0.0457 (13)0.0067 (10)0.0032 (11)0.0005 (9)
C10.0290 (16)0.0344 (15)0.0436 (17)0.0053 (12)0.0012 (13)0.0104 (13)
C20.0370 (17)0.0277 (14)0.0498 (18)0.0015 (12)0.0031 (14)0.0070 (13)
C30.0288 (15)0.0312 (15)0.0413 (17)0.0047 (11)0.0080 (12)0.0032 (12)
C40.0419 (18)0.0342 (15)0.0428 (18)0.0064 (13)0.0066 (14)0.0020 (13)
C50.0421 (18)0.0448 (17)0.0390 (17)0.0091 (14)0.0106 (14)0.0045 (13)
C60.0490 (19)0.0414 (17)0.0381 (17)0.0048 (14)0.0057 (14)0.0061 (13)
C70.0379 (17)0.0319 (15)0.0359 (16)0.0029 (12)0.0057 (13)0.0052 (12)
C80.0330 (15)0.0317 (15)0.0366 (16)0.0072 (12)0.0056 (12)0.0037 (12)
C90.0311 (16)0.0270 (15)0.0475 (18)0.0056 (12)0.0052 (13)0.0032 (13)
C100.0279 (15)0.0348 (15)0.0371 (16)0.0066 (12)0.0021 (12)0.0045 (12)
C110.0523 (19)0.0411 (17)0.0506 (19)0.0050 (14)0.0051 (15)0.0138 (14)
C120.093 (3)0.054 (2)0.053 (2)0.0128 (19)0.0125 (19)0.0167 (16)
C130.0379 (17)0.0420 (17)0.0388 (17)0.0089 (13)0.0020 (13)0.0068 (13)
C140.068 (2)0.0560 (19)0.0362 (17)0.0080 (16)0.0039 (15)0.0049 (14)
Geometric parameters (Å, º) top
O1—C51.365 (3)C6—C71.366 (4)
O1—C121.428 (3)C6—H6A0.9300
O2—C71.356 (3)C7—C81.422 (4)
O2—H2A0.8200C8—C91.418 (4)
O3—C91.335 (3)C9—C101.412 (4)
O3—H3A0.8200C10—C131.452 (4)
O4—C131.259 (3)C11—H11A0.9600
C1—C21.353 (4)C11—H11B0.9600
C1—C101.455 (3)C11—H11C0.9600
C1—C111.508 (4)C12—H12A0.9600
C2—C31.418 (4)C12—H12B0.9600
C2—H2B0.9300C12—H12C0.9600
C3—C41.404 (4)C13—C141.486 (4)
C3—C81.422 (3)C14—H14A0.9600
C4—C51.367 (4)C14—H14B0.9600
C4—H4A0.9300C14—H14C0.9600
C5—C61.393 (4)
C5—O1—C12117.6 (2)O3—C9—C10120.7 (2)
C7—O2—H2A109.5O3—C9—C8116.3 (2)
C9—O3—H3A109.5C10—C9—C8123.1 (2)
C2—C1—C10118.8 (2)C9—C10—C13117.1 (2)
C2—C1—C11116.9 (2)C9—C10—C1117.5 (2)
C10—C1—C11124.3 (2)C13—C10—C1125.5 (2)
C1—C2—C3124.4 (2)C1—C11—H11A109.5
C1—C2—H2B117.8C1—C11—H11B109.5
C3—C2—H2B117.8H11A—C11—H11B109.5
C4—C3—C2121.4 (2)C1—C11—H11C109.5
C4—C3—C8120.4 (2)H11A—C11—H11C109.5
C2—C3—C8118.2 (2)H11B—C11—H11C109.5
C5—C4—C3119.4 (3)O1—C12—H12A109.5
C5—C4—H4A120.3O1—C12—H12B109.5
C3—C4—H4A120.3H12A—C12—H12B109.5
O1—C5—C4124.4 (3)O1—C12—H12C109.5
O1—C5—C6114.4 (3)H12A—C12—H12C109.5
C4—C5—C6121.2 (3)H12B—C12—H12C109.5
C7—C6—C5120.8 (3)O4—C13—C10120.3 (2)
C7—C6—H6A119.6O4—C13—C14114.0 (2)
C5—C6—H6A119.6C10—C13—C14125.7 (2)
O2—C7—C6117.5 (2)C13—C14—H14A109.5
O2—C7—C8122.3 (2)C13—C14—H14B109.5
C6—C7—C8120.3 (2)H14A—C14—H14B109.5
C9—C8—C3118.0 (2)C13—C14—H14C109.5
C9—C8—C7124.0 (2)H14A—C14—H14C109.5
C3—C8—C7118.0 (2)H14B—C14—H14C109.5
C10—C1—C2—C30.2 (4)C6—C7—C8—C9179.0 (3)
C11—C1—C2—C3179.7 (2)O2—C7—C8—C3179.6 (2)
C1—C2—C3—C4179.7 (3)C6—C7—C8—C30.1 (4)
C1—C2—C3—C80.3 (4)C3—C8—C9—O3179.2 (2)
C2—C3—C4—C5179.6 (3)C7—C8—C9—O30.1 (4)
C8—C3—C4—C50.4 (4)C3—C8—C9—C101.0 (4)
C12—O1—C5—C41.7 (4)C7—C8—C9—C10179.9 (3)
C12—O1—C5—C6177.9 (3)O3—C9—C10—C130.0 (4)
C3—C4—C5—O1180.0 (2)C8—C9—C10—C13179.8 (2)
C3—C4—C5—C60.4 (4)O3—C9—C10—C1179.3 (2)
O1—C5—C6—C7179.7 (2)C8—C9—C10—C10.8 (4)
C4—C5—C6—C70.1 (4)C2—C1—C10—C90.4 (4)
C5—C6—C7—O2179.6 (2)C11—C1—C10—C9179.4 (2)
C5—C6—C7—C80.1 (4)C2—C1—C10—C13179.7 (2)
C4—C3—C8—C9179.3 (2)C11—C1—C10—C130.1 (4)
C2—C3—C8—C90.7 (4)C9—C10—C13—O40.8 (4)
C4—C3—C8—C70.1 (4)C1—C10—C13—O4178.5 (3)
C2—C3—C8—C7179.9 (2)C9—C10—C13—C14178.9 (3)
O2—C7—C8—C91.3 (4)C1—C10—C13—C141.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O30.821.852.570 (3)145
O3—H3A···O40.821.652.400 (3)150
 

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