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The title compound, C8H6O3, is an important perfume and is also used as an important intermediate in the fine-chemical industry. All non-H atoms of the molecule are coplanar. In the crystal structure, the molecules are stacked parallel to the crystallographic (010) plane.
Supporting information
CCDC reference: 274450
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.043
- wR factor = 0.119
- Data-to-parameter ratio = 11.5
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT031_ALERT_4_B Refined Extinction Parameter within Range ...... 1.67 Sigma
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.79 mm
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT432_ALERT_2_C Short Inter X...Y Contact O2 .. C5 .. 2.93 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact C3 .. C3 .. 3.18 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact C3 .. C3 .. 3.18 Ang.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
3,4-Methylenedioxybenzaldehyde
top
Crystal data top
C8H6O3 | Dx = 1.484 Mg m−3 |
Mr = 150.13 | Melting point: 310.15 K |
Orthorhombic, Pnma | Mo Kα radiation, λ = 0.71073 Å |
a = 7.1738 (14) Å | Cell parameters from 6628 reflections |
b = 6.3367 (13) Å | θ = 3.2–27.5° |
c = 14.782 (3) Å | µ = 0.12 mm−1 |
V = 672.0 (2) Å3 | T = 293 K |
Z = 4 | Plate, colourless |
F(000) = 312 | 0.79 × 0.19 × 0.07 mm |
Data collection top
Rigaku R-AXIS RAPID IP area-detector diffractometer | 840 independent reflections |
Radiation source: rotating anode | 631 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.060 |
oscillation scans | θmax = 27.5°, θmin = 3.2° |
Absorption correction: ψ scan (ABSCOR; Higashi, 1995) | h = −8→9 |
Tmin = 0.914, Tmax = 0.993 | k = −8→8 |
6193 measured reflections | l = −19→19 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.119 | w = 1/[σ2(Fo2) + (0.08P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max = 0.010 |
840 reflections | Δρmax = 0.33 e Å−3 |
73 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.005 (3) |
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 | x | y | z | Uiso*/Ueq | |
O1 | 1.20830 (19) | 0.7500 | −0.15880 (10) | 0.0291 (4) | |
O2 | 0.90763 (17) | 0.7500 | 0.16705 (9) | 0.0260 (4) | |
O3 | 0.58810 (18) | 0.7500 | 0.14463 (10) | 0.0313 (4) | |
C1 | 1.0387 (3) | 0.7500 | −0.16086 (14) | 0.0246 (4) | |
H1A | 0.9820 | 0.7500 | −0.2174 | 0.022 (5)* | |
C2 | 0.9165 (3) | 0.7500 | −0.08147 (13) | 0.0202 (4) | |
C3 | 0.9929 (2) | 0.7500 | 0.00617 (12) | 0.0201 (4) | |
H3A | 1.1209 | 0.7500 | 0.0159 | 0.020 (5)* | |
C4 | 0.8691 (3) | 0.7500 | 0.07594 (12) | 0.0206 (4) | |
C5 | 0.7315 (3) | 0.7500 | 0.21242 (13) | 0.0262 (5) | |
H5A | 0.7202 | 0.6258 | 0.2504 | 0.030 (4)* | |
C6 | 0.6770 (3) | 0.7500 | 0.06259 (14) | 0.0232 (4) | |
C7 | 0.5995 (3) | 0.7500 | −0.02203 (15) | 0.0277 (5) | |
H7A | 0.4712 | 0.7500 | −0.0307 | 0.034 (6)* | |
C8 | 0.7244 (3) | 0.7500 | −0.09465 (14) | 0.0248 (5) | |
H8A | 0.6777 | 0.7500 | −0.1533 | 0.031 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0242 (7) | 0.0364 (8) | 0.0265 (8) | 0.000 | 0.0048 (6) | 0.000 |
O2 | 0.0186 (7) | 0.0426 (8) | 0.0168 (7) | 0.000 | 0.0017 (5) | 0.000 |
O3 | 0.0175 (7) | 0.0518 (9) | 0.0245 (8) | 0.000 | 0.0052 (5) | 0.000 |
C1 | 0.0271 (10) | 0.0249 (9) | 0.0217 (9) | 0.000 | −0.0012 (8) | 0.000 |
C2 | 0.0200 (9) | 0.0188 (8) | 0.0219 (10) | 0.000 | 0.0018 (7) | 0.000 |
C3 | 0.0149 (8) | 0.0227 (8) | 0.0228 (10) | 0.000 | 0.0000 (7) | 0.000 |
C4 | 0.0203 (9) | 0.0216 (8) | 0.0198 (9) | 0.000 | −0.0020 (7) | 0.000 |
C5 | 0.0198 (9) | 0.0350 (10) | 0.0238 (11) | 0.000 | 0.0020 (8) | 0.000 |
C6 | 0.0163 (8) | 0.0266 (9) | 0.0266 (10) | 0.000 | 0.0034 (7) | 0.000 |
C7 | 0.0163 (8) | 0.0357 (10) | 0.0312 (11) | 0.000 | −0.0049 (8) | 0.000 |
C8 | 0.0225 (9) | 0.0290 (9) | 0.0229 (10) | 0.000 | −0.0043 (8) | 0.000 |
Geometric parameters (Å, º) top
O1—C1 | 1.217 (2) | C3—C4 | 1.361 (3) |
O2—C4 | 1.375 (2) | C3—H3A | 0.9296 |
O2—C5 | 1.431 (2) | C4—C6 | 1.392 (3) |
O3—C6 | 1.370 (2) | C5—H5A | 0.9700 |
O3—C5 | 1.436 (2) | C6—C7 | 1.369 (3) |
C1—C2 | 1.465 (3) | C7—C8 | 1.398 (3) |
C1—H1A | 0.9299 | C7—H7A | 0.9292 |
C2—C8 | 1.392 (3) | C8—H8A | 0.9297 |
C2—C3 | 1.406 (3) | | |
| | | |
C4—O2—C5 | 106.36 (14) | O2—C4—C6 | 109.74 (17) |
C6—O3—C5 | 106.51 (14) | O2—C5—O3 | 107.80 (15) |
O1—C1—C2 | 125.32 (19) | O2—C5—H5A | 110.2 |
O1—C1—H1A | 117.4 | O3—C5—H5A | 110.1 |
C2—C1—H1A | 117.3 | C7—C6—O3 | 128.29 (17) |
C8—C2—C3 | 120.96 (18) | C7—C6—C4 | 122.12 (18) |
C8—C2—C1 | 118.71 (18) | O3—C6—C4 | 109.60 (17) |
C3—C2—C1 | 120.33 (17) | C6—C7—C8 | 116.18 (18) |
C4—C3—C2 | 116.36 (17) | C6—C7—H7A | 121.9 |
C4—C3—H3A | 121.8 | C8—C7—H7A | 121.9 |
C2—C3—H3A | 121.8 | C2—C8—C7 | 121.8 (2) |
C3—C4—O2 | 127.68 (17) | C2—C8—H8A | 119.1 |
C3—C4—C6 | 122.58 (18) | C7—C8—H8A | 119.1 |
| | | |
O1—C1—C2—C8 | 180.0 | C5—O3—C6—C4 | 0.0 |
O1—C1—C2—C3 | 0.0 | C3—C4—C6—C7 | 0.0 |
C8—C2—C3—C4 | 0.0 | O2—C4—C6—C7 | 180.0 |
C1—C2—C3—C4 | 180.0 | C3—C4—C6—O3 | 180.0 |
C2—C3—C4—O2 | 180.0 | O2—C4—C6—O3 | 0.0 |
C2—C3—C4—C6 | 0.0 | O3—C6—C7—C8 | 180.0 |
C5—O2—C4—C3 | 180.0 | C4—C6—C7—C8 | 0.0 |
C5—O2—C4—C6 | 0.0 | C3—C2—C8—C7 | 0.000 (1) |
C4—O2—C5—O3 | 0.0 | C1—C2—C8—C7 | 180.0 |
C6—O3—C5—O2 | 0.0 | C6—C7—C8—C2 | 0.000 (1) |
C5—O3—C6—C7 | 180.0 | | |
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