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organic compounds
The molecule of the title compound, C14H14O4, is planar and the structural dimensions are in the normal ranges. There are two intramolecular O—HO hydrogen bonds, but no intermolecular interactions were observed.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804030181/sj6028sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804030181/sj6028Isup2.hkl |
CCDC reference: 262448
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (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
C14H14O4 | Z = 2 |
Mr = 246.25 | F(000) = 260 |
Triclinic, P1 | Dx = 1.441 Mg m−3 |
a = 6.993 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.543 (4) Å | Cell parameters from 518 reflections |
c = 11.058 (6) Å | θ = 1.8–25.0° |
α = 83.530 (9)° | µ = 0.11 mm−1 |
β = 85.171 (9)° | T = 273 K |
γ = 79.017 (9)° | Slab, yellow |
V = 567.7 (5) Å3 | 0.50 × 0.18 × 0.16 mm |
Data collection top
Bruker SMART APEX area-detector diffractometer | 1981 independent reflections |
Radiation source: fine-focus sealed tube | 1368 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
Detector resolution: 83.66 pixels mm-1 | θmax = 25.0°, θmin = 1.8° |
ω scans | h = −8→8 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −8→8 |
Tmin = 0.94, Tmax = 0.98 | l = −13→13 |
5437 measured reflections |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.148 | H-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 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.3227 (3) | 0.7118 (3) | 0.58026 (17) | 0.0539 (6) | |
O2 | 0.3927 (3) | 0.1637 (2) | 0.82437 (17) | 0.0511 (6) | |
H2A | 0.3856 | 0.1193 | 0.8954 | 0.077* | |
O3 | 0.3292 (3) | 0.1679 (2) | 1.05644 (16) | 0.0453 (5) | |
H3A | 0.3164 | 0.1280 | 1.1282 | 0.068* | |
O4 | 0.2702 (3) | 0.1624 (3) | 1.27364 (18) | 0.0533 (6) | |
C1 | 0.1800 (4) | 0.6392 (3) | 1.1342 (2) | 0.0353 (7) | |
C2 | 0.1907 (4) | 0.7227 (3) | 1.0196 (3) | 0.0385 (7) | |
H2B | 0.1600 | 0.8488 | 1.0099 | 0.046* | |
C3 | 0.2456 (4) | 0.6311 (3) | 0.9134 (2) | 0.0336 (7) | |
C4 | 0.2545 (4) | 0.7267 (4) | 0.7971 (2) | 0.0400 (7) | |
H4A | 0.2235 | 0.8528 | 0.7882 | 0.048* | |
C5 | 0.3092 (4) | 0.6330 (4) | 0.6972 (3) | 0.0420 (7) | |
C6 | 0.3552 (4) | 0.4441 (4) | 0.7086 (2) | 0.0429 (7) | |
H6A | 0.3918 | 0.3833 | 0.6393 | 0.052* | |
C7 | 0.3472 (4) | 0.3471 (3) | 0.8204 (2) | 0.0353 (7) | |
C8 | 0.2919 (4) | 0.4382 (3) | 0.9273 (2) | 0.0334 (6) | |
C9 | 0.2825 (4) | 0.3488 (3) | 1.0469 (2) | 0.0350 (7) | |
C10 | 0.2268 (4) | 0.4420 (3) | 1.1518 (2) | 0.0331 (6) | |
C11 | 0.1199 (4) | 0.7595 (4) | 1.2361 (3) | 0.0482 (8) | |
H11A | 0.0965 | 0.8843 | 1.2028 | 0.072* | |
H11B | 0.2221 | 0.7402 | 1.2915 | 0.072* | |
H11C | 0.0027 | 0.7307 | 1.2789 | 0.072* | |
C12 | 0.2712 (5) | 0.9049 (4) | 0.5610 (3) | 0.0680 (10) | |
H12A | 0.2869 | 0.9431 | 0.4755 | 0.102* | |
H12B | 0.3544 | 0.9588 | 0.6049 | 0.102* | |
H12C | 0.1378 | 0.9427 | 0.5896 | 0.102* | |
C13 | 0.2231 (4) | 0.3326 (4) | 1.2684 (2) | 0.0392 (7) | |
C14 | 0.1659 (5) | 0.4031 (4) | 1.3890 (3) | 0.0541 (9) | |
H14A | 0.1757 | 0.3036 | 1.4518 | 0.081* | |
H14B | 0.0338 | 0.4683 | 1.3893 | 0.081* | |
H14C | 0.2512 | 0.4831 | 1.4037 | 0.081* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0713 (15) | 0.0507 (13) | 0.0368 (12) | −0.0089 (11) | −0.0078 (10) | 0.0072 (9) |
O2 | 0.0791 (16) | 0.0326 (11) | 0.0408 (12) | −0.0031 (10) | −0.0094 (11) | −0.0083 (9) |
O3 | 0.0676 (14) | 0.0290 (10) | 0.0371 (11) | −0.0065 (9) | −0.0011 (10) | −0.0004 (8) |
O4 | 0.0723 (15) | 0.0382 (12) | 0.0457 (13) | −0.0067 (10) | 0.0032 (11) | 0.0005 (9) |
C1 | 0.0290 (16) | 0.0344 (15) | 0.0436 (17) | −0.0053 (12) | −0.0012 (13) | −0.0104 (13) |
C2 | 0.0370 (17) | 0.0277 (14) | 0.0498 (18) | −0.0015 (12) | −0.0031 (14) | −0.0070 (13) |
C3 | 0.0288 (15) | 0.0312 (15) | 0.0413 (17) | −0.0047 (11) | −0.0080 (12) | −0.0032 (12) |
C4 | 0.0419 (18) | 0.0342 (15) | 0.0428 (18) | −0.0064 (13) | −0.0066 (14) | 0.0020 (13) |
C5 | 0.0421 (18) | 0.0448 (17) | 0.0390 (17) | −0.0091 (14) | −0.0106 (14) | 0.0045 (13) |
C6 | 0.0490 (19) | 0.0414 (17) | 0.0381 (17) | −0.0048 (14) | −0.0057 (14) | −0.0061 (13) |
C7 | 0.0379 (17) | 0.0319 (15) | 0.0359 (16) | −0.0029 (12) | −0.0057 (13) | −0.0052 (12) |
C8 | 0.0330 (15) | 0.0317 (15) | 0.0366 (16) | −0.0072 (12) | −0.0056 (12) | −0.0037 (12) |
C9 | 0.0311 (16) | 0.0270 (15) | 0.0475 (18) | −0.0056 (12) | −0.0052 (13) | −0.0032 (13) |
C10 | 0.0279 (15) | 0.0348 (15) | 0.0371 (16) | −0.0066 (12) | −0.0021 (12) | −0.0045 (12) |
C11 | 0.0523 (19) | 0.0411 (17) | 0.0506 (19) | −0.0050 (14) | 0.0051 (15) | −0.0138 (14) |
C12 | 0.093 (3) | 0.054 (2) | 0.053 (2) | −0.0128 (19) | −0.0125 (19) | 0.0167 (16) |
C13 | 0.0379 (17) | 0.0420 (17) | 0.0388 (17) | −0.0089 (13) | −0.0020 (13) | −0.0068 (13) |
C14 | 0.068 (2) | 0.0560 (19) | 0.0362 (17) | −0.0080 (16) | 0.0039 (15) | −0.0049 (14) |
Geometric parameters (Å, º) top
O1—C5 | 1.365 (3) | C6—C7 | 1.366 (4) |
O1—C12 | 1.428 (3) | C6—H6A | 0.9300 |
O2—C7 | 1.356 (3) | C7—C8 | 1.422 (4) |
O2—H2A | 0.8200 | C8—C9 | 1.418 (4) |
O3—C9 | 1.335 (3) | C9—C10 | 1.412 (4) |
O3—H3A | 0.8200 | C10—C13 | 1.452 (4) |
O4—C13 | 1.259 (3) | C11—H11A | 0.9600 |
C1—C2 | 1.353 (4) | C11—H11B | 0.9600 |
C1—C10 | 1.455 (3) | C11—H11C | 0.9600 |
C1—C11 | 1.508 (4) | C12—H12A | 0.9600 |
C2—C3 | 1.418 (4) | C12—H12B | 0.9600 |
C2—H2B | 0.9300 | C12—H12C | 0.9600 |
C3—C4 | 1.404 (4) | C13—C14 | 1.486 (4) |
C3—C8 | 1.422 (3) | C14—H14A | 0.9600 |
C4—C5 | 1.367 (4) | C14—H14B | 0.9600 |
C4—H4A | 0.9300 | C14—H14C | 0.9600 |
C5—C6 | 1.393 (4) | ||
C5—O1—C12 | 117.6 (2) | O3—C9—C10 | 120.7 (2) |
C7—O2—H2A | 109.5 | O3—C9—C8 | 116.3 (2) |
C9—O3—H3A | 109.5 | C10—C9—C8 | 123.1 (2) |
C2—C1—C10 | 118.8 (2) | C9—C10—C13 | 117.1 (2) |
C2—C1—C11 | 116.9 (2) | C9—C10—C1 | 117.5 (2) |
C10—C1—C11 | 124.3 (2) | C13—C10—C1 | 125.5 (2) |
C1—C2—C3 | 124.4 (2) | C1—C11—H11A | 109.5 |
C1—C2—H2B | 117.8 | C1—C11—H11B | 109.5 |
C3—C2—H2B | 117.8 | H11A—C11—H11B | 109.5 |
C4—C3—C2 | 121.4 (2) | C1—C11—H11C | 109.5 |
C4—C3—C8 | 120.4 (2) | H11A—C11—H11C | 109.5 |
C2—C3—C8 | 118.2 (2) | H11B—C11—H11C | 109.5 |
C5—C4—C3 | 119.4 (3) | O1—C12—H12A | 109.5 |
C5—C4—H4A | 120.3 | O1—C12—H12B | 109.5 |
C3—C4—H4A | 120.3 | H12A—C12—H12B | 109.5 |
O1—C5—C4 | 124.4 (3) | O1—C12—H12C | 109.5 |
O1—C5—C6 | 114.4 (3) | H12A—C12—H12C | 109.5 |
C4—C5—C6 | 121.2 (3) | H12B—C12—H12C | 109.5 |
C7—C6—C5 | 120.8 (3) | O4—C13—C10 | 120.3 (2) |
C7—C6—H6A | 119.6 | O4—C13—C14 | 114.0 (2) |
C5—C6—H6A | 119.6 | C10—C13—C14 | 125.7 (2) |
O2—C7—C6 | 117.5 (2) | C13—C14—H14A | 109.5 |
O2—C7—C8 | 122.3 (2) | C13—C14—H14B | 109.5 |
C6—C7—C8 | 120.3 (2) | H14A—C14—H14B | 109.5 |
C9—C8—C3 | 118.0 (2) | C13—C14—H14C | 109.5 |
C9—C8—C7 | 124.0 (2) | H14A—C14—H14C | 109.5 |
C3—C8—C7 | 118.0 (2) | H14B—C14—H14C | 109.5 |
C10—C1—C2—C3 | −0.2 (4) | C6—C7—C8—C9 | −179.0 (3) |
C11—C1—C2—C3 | 179.7 (2) | O2—C7—C8—C3 | −179.6 (2) |
C1—C2—C3—C4 | −179.7 (3) | C6—C7—C8—C3 | 0.1 (4) |
C1—C2—C3—C8 | 0.3 (4) | C3—C8—C9—O3 | −179.2 (2) |
C2—C3—C4—C5 | 179.6 (3) | C7—C8—C9—O3 | −0.1 (4) |
C8—C3—C4—C5 | −0.4 (4) | C3—C8—C9—C10 | 1.0 (4) |
C12—O1—C5—C4 | −1.7 (4) | C7—C8—C9—C10 | −179.9 (3) |
C12—O1—C5—C6 | 177.9 (3) | O3—C9—C10—C13 | 0.0 (4) |
C3—C4—C5—O1 | 180.0 (2) | C8—C9—C10—C13 | 179.8 (2) |
C3—C4—C5—C6 | 0.4 (4) | O3—C9—C10—C1 | 179.3 (2) |
O1—C5—C6—C7 | −179.7 (2) | C8—C9—C10—C1 | −0.8 (4) |
C4—C5—C6—C7 | −0.1 (4) | C2—C1—C10—C9 | 0.4 (4) |
C5—C6—C7—O2 | 179.6 (2) | C11—C1—C10—C9 | −179.4 (2) |
C5—C6—C7—C8 | −0.1 (4) | C2—C1—C10—C13 | 179.7 (2) |
C4—C3—C8—C9 | 179.3 (2) | C11—C1—C10—C13 | −0.1 (4) |
C2—C3—C8—C9 | −0.7 (4) | C9—C10—C13—O4 | 0.8 (4) |
C4—C3—C8—C7 | 0.1 (4) | C1—C10—C13—O4 | −178.5 (3) |
C2—C3—C8—C7 | −179.9 (2) | C9—C10—C13—C14 | −178.9 (3) |
O2—C7—C8—C9 | 1.3 (4) | C1—C10—C13—C14 | 1.7 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O3 | 0.82 | 1.85 | 2.570 (3) | 145 |
O3—H3A···O4 | 0.82 | 1.65 | 2.400 (3) | 150 |
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