In the title compound, C
15H
14O
5S, the ethylvanillin group makes a dihedral angle of 43.97 (8)° with the phenyl ring. The packing is stabilized by weak non-classical intermolecular C—H
O hydrogen bonds that link the molecules into zigzag chains.
Supporting information
CCDC reference: 633980
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C)= 0.004 Å
- R factor = 0.043
- wR factor = 0.118
- Data-to-parameter ratio = 13.6
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Author = China, Tianjin University of Traditional Chinese Medicine Tianjin 300193 People's Republic of China and Key Laboratory of the Pharmacology of Traditional Chinese Medical Formulae Tianjin University of Traditional Chinese Medicine Ministry of Education Tianjin 300193 People's Republic of
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Author = China, Tianjin University of Traditional Chinese Medicine Tianjin 300193 People's Republic of China and Key Laboratory of the Pharmacology of Traditional Chinese Medical Formulae Tianjin University of Traditional Chinese Medicine Ministry of Education Tianjin 300193 People's Republic of
2 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
2-Ethoxy-4-formylphenyl benzenesulfonate
top
Crystal data top
C15H14O5S | F(000) = 1280 |
Mr = 306.33 | Dx = 1.375 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 2495 reflections |
a = 7.5538 (15) Å | θ = 2.8–22.6° |
b = 13.511 (3) Å | µ = 0.24 mm−1 |
c = 28.994 (6) Å | T = 294 K |
V = 2959.1 (11) Å3 | Block, colourless |
Z = 8 | 0.24 × 0.18 × 0.12 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 2601 independent reflections |
Radiation source: fine-focus sealed tube | 1556 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.054 |
φ and ω scans | θmax = 25.0°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→8 |
Tmin = 0.928, Tmax = 0.972 | k = −15→16 |
12380 measured reflections | l = −20→34 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0507P)2 + 0.9638P] where P = (Fo2 + 2Fc2)/3 |
2601 reflections | (Δ/σ)max = 0.001 |
191 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−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 >
2σ(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 | |
S1 | 0.98655 (11) | 0.54549 (5) | 0.35464 (3) | 0.0560 (3) | |
O1 | 1.0494 (3) | 0.59909 (14) | 0.31596 (8) | 0.0796 (7) | |
O2 | 0.9381 (3) | 0.59584 (14) | 0.39575 (7) | 0.0798 (7) | |
O3 | 1.1475 (2) | 0.47214 (13) | 0.36623 (6) | 0.0543 (5) | |
O4 | 1.0799 (2) | 0.28082 (11) | 0.35510 (6) | 0.0500 (5) | |
O5 | 1.1511 (4) | 0.13302 (18) | 0.51921 (8) | 0.0914 (8) | |
C1 | 0.8150 (3) | 0.46669 (18) | 0.33826 (9) | 0.0446 (7) | |
C2 | 0.7939 (4) | 0.4446 (2) | 0.29202 (10) | 0.0544 (7) | |
H2 | 0.8687 | 0.4732 | 0.2703 | 0.065* | |
C3 | 0.6639 (5) | 0.3811 (2) | 0.27810 (12) | 0.0692 (9) | |
H3 | 0.6492 | 0.3665 | 0.2470 | 0.083* | |
C4 | 0.5559 (5) | 0.3393 (2) | 0.31031 (15) | 0.0793 (10) | |
H4 | 0.4684 | 0.2953 | 0.3009 | 0.095* | |
C5 | 0.5733 (4) | 0.3606 (2) | 0.35621 (14) | 0.0779 (10) | |
H5 | 0.4976 | 0.3316 | 0.3776 | 0.093* | |
C6 | 0.7050 (4) | 0.4261 (2) | 0.37092 (10) | 0.0608 (8) | |
H6 | 0.7179 | 0.4417 | 0.4020 | 0.073* | |
C7 | 1.1407 (4) | 0.41166 (19) | 0.40593 (10) | 0.0480 (7) | |
C8 | 1.1759 (4) | 0.4503 (2) | 0.44858 (11) | 0.0641 (9) | |
H8 | 1.1963 | 0.5178 | 0.4520 | 0.077* | |
C9 | 1.1810 (4) | 0.3887 (2) | 0.48639 (11) | 0.0676 (9) | |
H9 | 1.2037 | 0.4147 | 0.5155 | 0.081* | |
C10 | 1.1524 (4) | 0.2887 (2) | 0.48109 (9) | 0.0562 (8) | |
C11 | 1.1170 (4) | 0.2497 (2) | 0.43751 (9) | 0.0505 (7) | |
H11 | 1.0980 | 0.1820 | 0.4342 | 0.061* | |
C12 | 1.1099 (3) | 0.31037 (18) | 0.39925 (9) | 0.0446 (7) | |
C13 | 1.0272 (4) | 0.17956 (19) | 0.34847 (9) | 0.0530 (7) | |
H13A | 0.9165 | 0.1667 | 0.3643 | 0.064* | |
H13B | 1.1167 | 0.1352 | 0.3607 | 0.064* | |
C14 | 1.0055 (4) | 0.1636 (2) | 0.29762 (9) | 0.0661 (9) | |
H14A | 0.9113 | 0.2047 | 0.2863 | 0.099* | |
H14B | 0.9777 | 0.0954 | 0.2918 | 0.099* | |
H14C | 1.1136 | 0.1806 | 0.2821 | 0.099* | |
C15 | 1.1639 (5) | 0.2217 (3) | 0.52091 (11) | 0.0756 (10) | |
H15 | 1.1824 | 0.2501 | 0.5497 | 0.091* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0707 (5) | 0.0348 (4) | 0.0625 (5) | −0.0008 (4) | −0.0049 (4) | 0.0028 (4) |
O1 | 0.0943 (17) | 0.0540 (12) | 0.0907 (16) | −0.0226 (12) | −0.0053 (13) | 0.0323 (12) |
O2 | 0.1094 (19) | 0.0536 (12) | 0.0763 (15) | 0.0201 (12) | −0.0150 (13) | −0.0225 (11) |
O3 | 0.0537 (12) | 0.0434 (10) | 0.0656 (13) | −0.0053 (9) | −0.0011 (9) | 0.0026 (10) |
O4 | 0.0666 (13) | 0.0359 (9) | 0.0475 (11) | −0.0016 (9) | −0.0025 (9) | −0.0030 (8) |
O5 | 0.141 (2) | 0.0704 (16) | 0.0627 (15) | 0.0151 (15) | −0.0091 (14) | 0.0090 (13) |
C1 | 0.0522 (17) | 0.0365 (14) | 0.0452 (16) | 0.0068 (12) | 0.0037 (13) | 0.0062 (13) |
C2 | 0.0585 (19) | 0.0471 (16) | 0.0577 (19) | 0.0064 (15) | 0.0035 (15) | 0.0031 (15) |
C3 | 0.075 (2) | 0.058 (2) | 0.075 (2) | 0.0080 (18) | −0.0181 (19) | −0.0064 (18) |
C4 | 0.066 (2) | 0.063 (2) | 0.109 (3) | −0.0025 (18) | −0.026 (2) | 0.011 (2) |
C5 | 0.053 (2) | 0.074 (2) | 0.106 (3) | −0.0040 (18) | 0.013 (2) | 0.035 (2) |
C6 | 0.062 (2) | 0.0603 (19) | 0.060 (2) | 0.0077 (17) | 0.0084 (16) | 0.0159 (15) |
C7 | 0.0473 (17) | 0.0426 (15) | 0.0543 (18) | −0.0017 (13) | −0.0050 (14) | 0.0013 (14) |
C8 | 0.075 (2) | 0.0481 (17) | 0.069 (2) | −0.0008 (16) | −0.0176 (17) | −0.0134 (17) |
C9 | 0.084 (3) | 0.066 (2) | 0.0536 (19) | 0.0119 (17) | −0.0203 (17) | −0.0146 (17) |
C10 | 0.068 (2) | 0.0574 (18) | 0.0434 (17) | 0.0134 (15) | −0.0082 (15) | −0.0028 (15) |
C11 | 0.0568 (18) | 0.0417 (14) | 0.0529 (18) | 0.0081 (14) | −0.0045 (14) | 0.0000 (14) |
C12 | 0.0458 (17) | 0.0424 (15) | 0.0455 (16) | 0.0043 (13) | −0.0060 (13) | −0.0071 (13) |
C13 | 0.069 (2) | 0.0385 (14) | 0.0510 (17) | −0.0030 (14) | 0.0056 (15) | −0.0050 (13) |
C14 | 0.084 (2) | 0.0545 (18) | 0.0594 (19) | −0.0075 (17) | −0.0003 (17) | −0.0133 (15) |
C15 | 0.095 (3) | 0.082 (3) | 0.050 (2) | 0.021 (2) | −0.0124 (18) | −0.0055 (19) |
Geometric parameters (Å, º) top
S1—O1 | 1.417 (2) | C6—H6 | 0.9300 |
S1—O2 | 1.420 (2) | C7—C8 | 1.368 (4) |
S1—O3 | 1.6043 (19) | C7—C12 | 1.402 (3) |
S1—C1 | 1.743 (3) | C8—C9 | 1.377 (4) |
O3—C7 | 1.413 (3) | C8—H8 | 0.9300 |
O4—C12 | 1.360 (3) | C9—C10 | 1.377 (4) |
O4—C13 | 1.438 (3) | C9—H9 | 0.9300 |
O5—C15 | 1.203 (4) | C10—C11 | 1.395 (4) |
C1—C6 | 1.374 (4) | C10—C15 | 1.469 (4) |
C1—C2 | 1.383 (4) | C11—C12 | 1.381 (3) |
C2—C3 | 1.366 (4) | C11—H11 | 0.9300 |
C2—H2 | 0.9300 | C13—C14 | 1.499 (3) |
C3—C4 | 1.362 (5) | C13—H13A | 0.9700 |
C3—H3 | 0.9300 | C13—H13B | 0.9700 |
C4—C5 | 1.368 (5) | C14—H14A | 0.9600 |
C4—H4 | 0.9300 | C14—H14B | 0.9600 |
C5—C6 | 1.398 (4) | C14—H14C | 0.9600 |
C5—H5 | 0.9300 | C15—H15 | 0.9300 |
| | | |
O1—S1—O2 | 120.37 (14) | C7—C8—H8 | 120.2 |
O1—S1—O3 | 103.14 (12) | C9—C8—H8 | 120.2 |
O2—S1—O3 | 108.38 (11) | C8—C9—C10 | 120.0 (3) |
O1—S1—C1 | 110.24 (13) | C8—C9—H9 | 120.0 |
O2—S1—C1 | 109.25 (14) | C10—C9—H9 | 120.0 |
O3—S1—C1 | 104.08 (11) | C9—C10—C11 | 120.1 (3) |
C7—O3—S1 | 120.02 (16) | C9—C10—C15 | 120.5 (3) |
C12—O4—C13 | 116.83 (19) | C11—C10—C15 | 119.3 (3) |
C6—C1—C2 | 120.8 (3) | C12—C11—C10 | 120.7 (3) |
C6—C1—S1 | 120.4 (2) | C12—C11—H11 | 119.7 |
C2—C1—S1 | 118.8 (2) | C10—C11—H11 | 119.7 |
C3—C2—C1 | 120.3 (3) | O4—C12—C11 | 126.0 (2) |
C3—C2—H2 | 119.8 | O4—C12—C7 | 116.4 (2) |
C1—C2—H2 | 119.8 | C11—C12—C7 | 117.6 (2) |
C4—C3—C2 | 119.3 (3) | O4—C13—C14 | 107.4 (2) |
C4—C3—H3 | 120.4 | O4—C13—H13A | 110.2 |
C2—C3—H3 | 120.4 | C14—C13—H13A | 110.2 |
C3—C4—C5 | 121.5 (3) | O4—C13—H13B | 110.2 |
C3—C4—H4 | 119.3 | C14—C13—H13B | 110.2 |
C5—C4—H4 | 119.3 | H13A—C13—H13B | 108.5 |
C4—C5—C6 | 119.9 (3) | C13—C14—H14A | 109.5 |
C4—C5—H5 | 120.0 | C13—C14—H14B | 109.5 |
C6—C5—H5 | 120.0 | H14A—C14—H14B | 109.5 |
C1—C6—C5 | 118.2 (3) | C13—C14—H14C | 109.5 |
C1—C6—H6 | 120.9 | H14A—C14—H14C | 109.5 |
C5—C6—H6 | 120.9 | H14B—C14—H14C | 109.5 |
C8—C7—C12 | 122.0 (3) | O5—C15—C10 | 125.2 (3) |
C8—C7—O3 | 120.6 (2) | O5—C15—H15 | 117.4 |
C12—C7—O3 | 117.3 (2) | C10—C15—H15 | 117.4 |
C7—C8—C9 | 119.6 (3) | | |
| | | |
O1—S1—O3—C7 | 174.35 (18) | C12—C7—C8—C9 | −0.3 (4) |
O2—S1—O3—C7 | 45.7 (2) | O3—C7—C8—C9 | −175.4 (3) |
C1—S1—O3—C7 | −70.5 (2) | C7—C8—C9—C10 | 0.6 (5) |
O1—S1—C1—C6 | −163.8 (2) | C8—C9—C10—C11 | −0.5 (5) |
O2—S1—C1—C6 | −29.4 (3) | C8—C9—C10—C15 | 177.8 (3) |
O3—S1—C1—C6 | 86.2 (2) | C9—C10—C11—C12 | −0.1 (4) |
O1—S1—C1—C2 | 17.3 (2) | C15—C10—C11—C12 | −178.4 (3) |
O2—S1—C1—C2 | 151.7 (2) | C13—O4—C12—C11 | 9.0 (4) |
O3—S1—C1—C2 | −92.7 (2) | C13—O4—C12—C7 | −172.7 (2) |
C6—C1—C2—C3 | −0.6 (4) | C10—C11—C12—O4 | 178.7 (3) |
S1—C1—C2—C3 | 178.2 (2) | C10—C11—C12—C7 | 0.4 (4) |
C1—C2—C3—C4 | −0.4 (4) | C8—C7—C12—O4 | −178.7 (2) |
C2—C3—C4—C5 | 0.9 (5) | O3—C7—C12—O4 | −3.5 (3) |
C3—C4—C5—C6 | −0.5 (5) | C8—C7—C12—C11 | −0.3 (4) |
C2—C1—C6—C5 | 1.1 (4) | O3—C7—C12—C11 | 175.0 (2) |
S1—C1—C6—C5 | −177.8 (2) | C12—O4—C13—C14 | −178.9 (2) |
C4—C5—C6—C1 | −0.5 (5) | C9—C10—C15—O5 | −175.5 (4) |
S1—O3—C7—C8 | −78.1 (3) | C11—C10—C15—O5 | 2.8 (5) |
S1—O3—C7—C12 | 106.6 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O5i | 0.93 | 2.55 | 3.309 (4) | 139 |
Symmetry code: (i) x−1/2, −y+1/2, −z+1. |