5-Formyl-2-methoxy­phenyl benzene­sulfonate

In the title compound, C₁₄H₁₂O₅S, the isovanillin group makes a dihedral angle of 37.45 (15)° with the phenyl ring. The crystal packing is stabilized by a weak non-classical inter­molecular C—H...O hydrogen bond that links mol­ecules into a chain.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.050
• wR factor = 0.137
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 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
   1 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

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Computing details

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.

5-Formyl-2-methoxyphenyl benzenesulfonate

Crystal data

C14H12O5S	Z = 2
Mr = 292.31	F(000) = 304
Triclinic, P1	Dx = 1.425 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.915 (7) Å	Cell parameters from 888 reflections
b = 8.255 (8) Å	θ = 2.6–22.2°
c = 11.581 (10) Å	µ = 0.25 mm^−1
α = 102.684 (14)°	T = 294 K
β = 109.208 (13)°	Block, colorless
γ = 97.137 (13)°	0.28 × 0.26 × 0.16 mm
V = 681.1 (11) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2365 independent reflections
Radiation source: fine-focus sealed tube	1404 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
Tmin = 0.918, Tmax = 0.960	k = −9→9
3291 measured reflections	l = −13→12

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.137	w = 1/[σ^2(Fo^2) + (0.066P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.004
2365 reflections	Δρmax = 0.24 e Å^−3
183 parameters	Δρmin = −0.40 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.064 (8)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.37133 (13)	0.02978 (10)	0.72451 (8)	0.0500 (3)
O1	0.4983 (4)	−0.0316 (3)	0.8127 (2)	0.0705 (8)
O2	0.2917 (4)	−0.0652 (3)	0.5944 (2)	0.0618 (7)
O3	0.4871 (3)	0.2093 (3)	0.73498 (19)	0.0485 (6)
O4	0.3755 (3)	0.4696 (3)	0.8412 (2)	0.0593 (7)
O5	0.1737 (5)	0.3980 (4)	0.2506 (3)	0.1012 (11)
C1	0.1996 (5)	0.0837 (4)	0.7783 (3)	0.0461 (8)
C2	0.0405 (5)	0.1057 (4)	0.6948 (3)	0.0541 (9)
H2	0.0210	0.0836	0.6086	0.065*
C3	−0.0880 (6)	0.1598 (5)	0.7384 (4)	0.0755 (12)
H3	−0.1955	0.1755	0.6822	0.091*
C4	−0.0593 (7)	0.1911 (6)	0.8650 (5)	0.0942 (15)
H4	−0.1478	0.2283	0.8944	0.113*
C5	0.0973 (8)	0.1685 (6)	0.9487 (4)	0.0920 (15)
H5	0.1152	0.1902	1.0347	0.110*
C6	0.2300 (6)	0.1131 (5)	0.9056 (3)	0.0686 (11)
H6	0.3371	0.0963	0.9617	0.082*
C7	0.3974 (4)	0.3064 (4)	0.6580 (3)	0.0434 (8)
C8	0.3409 (5)	0.4436 (4)	0.7161 (3)	0.0459 (8)
C9	0.2539 (5)	0.5420 (4)	0.6422 (3)	0.0529 (9)
H9	0.2132	0.6339	0.6783	0.063*
C10	0.2283 (5)	0.5026 (4)	0.5150 (3)	0.0547 (10)
H10	0.1716	0.5701	0.4663	0.066*
C11	0.2841 (5)	0.3668 (4)	0.4582 (3)	0.0485 (9)
C12	0.3744 (5)	0.2689 (4)	0.5318 (3)	0.0496 (9)
H12	0.4184	0.1793	0.4959	0.060*
C13	0.2562 (6)	0.3254 (5)	0.3233 (4)	0.0717 (12)
H13	0.3054	0.2373	0.2913	0.086*
C14	0.2966 (6)	0.5937 (5)	0.9013 (3)	0.0772 (13)
H14A	0.3423	0.7036	0.8953	0.116*
H14B	0.3288	0.5963	0.9893	0.116*
H14C	0.1657	0.5644	0.8596	0.116*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0559 (7)	0.0487 (5)	0.0509 (6)	0.0226 (4)	0.0184 (5)	0.0198 (4)
O1	0.066 (2)	0.0759 (17)	0.0846 (18)	0.0393 (14)	0.0226 (15)	0.0474 (14)
O2	0.082 (2)	0.0486 (13)	0.0548 (14)	0.0228 (12)	0.0263 (14)	0.0081 (11)
O3	0.0387 (16)	0.0539 (13)	0.0552 (13)	0.0169 (11)	0.0137 (11)	0.0216 (11)
O4	0.0685 (19)	0.0599 (14)	0.0442 (13)	0.0246 (13)	0.0128 (13)	0.0102 (11)
O5	0.134 (3)	0.128 (3)	0.0599 (18)	0.063 (2)	0.0351 (19)	0.0420 (18)
C1	0.047 (2)	0.0524 (18)	0.0382 (18)	0.0079 (16)	0.0155 (17)	0.0132 (14)
C2	0.043 (3)	0.072 (2)	0.0421 (19)	0.0105 (19)	0.0109 (18)	0.0154 (17)
C3	0.049 (3)	0.102 (3)	0.070 (3)	0.016 (2)	0.021 (2)	0.015 (2)
C4	0.062 (4)	0.139 (4)	0.085 (3)	0.021 (3)	0.043 (3)	0.011 (3)
C5	0.083 (4)	0.139 (4)	0.050 (2)	0.003 (3)	0.036 (3)	0.012 (3)
C6	0.065 (3)	0.095 (3)	0.047 (2)	0.011 (2)	0.021 (2)	0.026 (2)
C7	0.032 (2)	0.0453 (17)	0.054 (2)	0.0099 (15)	0.0126 (16)	0.0199 (15)
C8	0.041 (2)	0.0467 (18)	0.0435 (19)	0.0083 (16)	0.0101 (16)	0.0086 (14)
C9	0.057 (3)	0.0415 (17)	0.058 (2)	0.0170 (17)	0.0177 (19)	0.0118 (16)
C10	0.055 (3)	0.0523 (19)	0.055 (2)	0.0151 (18)	0.0116 (19)	0.0226 (17)
C11	0.043 (2)	0.0567 (19)	0.051 (2)	0.0129 (17)	0.0190 (17)	0.0207 (16)
C12	0.043 (2)	0.0550 (19)	0.058 (2)	0.0173 (17)	0.0247 (18)	0.0166 (16)
C13	0.083 (3)	0.083 (3)	0.061 (2)	0.031 (2)	0.032 (2)	0.029 (2)
C14	0.094 (4)	0.077 (3)	0.052 (2)	0.037 (2)	0.018 (2)	0.0034 (19)

Geometric parameters (Å, º)

S1—O1	1.410 (2)	C5—H5	0.9300
S1—O2	1.420 (3)	C6—H6	0.9300
S1—O3	1.600 (3)	C7—C12	1.370 (4)
S1—C1	1.737 (4)	C7—C8	1.387 (4)
O3—C7	1.408 (3)	C8—C9	1.387 (4)
O4—C8	1.344 (4)	C9—C10	1.376 (5)
O4—C14	1.434 (4)	C9—H9	0.9300
O5—C13	1.204 (4)	C10—C11	1.370 (5)
C1—C2	1.374 (5)	C10—H10	0.9300
C1—C6	1.373 (5)	C11—C12	1.391 (4)
C2—C3	1.357 (5)	C11—C13	1.458 (5)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.367 (6)	C13—H13	0.9300
C3—H3	0.9300	C14—H14A	0.9600
C4—C5	1.363 (6)	C14—H14B	0.9600
C4—H4	0.9300	C14—H14C	0.9600
C5—C6	1.388 (6)
O1—S1—O2	119.91 (16)	C12—C7—O3	120.4 (3)
O1—S1—O3	102.81 (15)	C8—C7—O3	117.4 (3)
O2—S1—O3	108.61 (13)	O4—C8—C9	125.3 (3)
O1—S1—C1	110.97 (17)	O4—C8—C7	116.4 (3)
O2—S1—C1	109.41 (17)	C9—C8—C7	118.3 (3)
O3—S1—C1	103.70 (14)	C10—C9—C8	119.5 (3)
C7—O3—S1	117.3 (2)	C10—C9—H9	120.2
C8—O4—C14	118.3 (3)	C8—C9—H9	120.2
C2—C1—C6	121.0 (3)	C11—C10—C9	121.9 (3)
C2—C1—S1	119.8 (3)	C11—C10—H10	119.1
C6—C1—S1	119.1 (3)	C9—C10—H10	119.1
C3—C2—C1	119.8 (3)	C10—C11—C12	119.2 (3)
C3—C2—H2	120.1	C10—C11—C13	121.6 (3)
C1—C2—H2	120.1	C12—C11—C13	119.2 (3)
C2—C3—C4	120.0 (4)	C7—C12—C11	119.0 (3)
C2—C3—H3	120.0	C7—C12—H12	120.5
C4—C3—H3	120.0	C11—C12—H12	120.5
C5—C4—C3	120.8 (4)	O5—C13—C11	124.3 (4)
C5—C4—H4	119.6	O5—C13—H13	117.9
C3—C4—H4	119.6	C11—C13—H13	117.9
C4—C5—C6	119.9 (4)	O4—C14—H14A	109.5
C4—C5—H5	120.0	O4—C14—H14B	109.5
C6—C5—H5	120.0	H14A—C14—H14B	109.5
C1—C6—C5	118.4 (4)	O4—C14—H14C	109.5
C1—C6—H6	120.8	H14A—C14—H14C	109.5
C5—C6—H6	120.8	H14B—C14—H14C	109.5
C12—C7—C8	122.1 (3)
O1—S1—O3—C7	−179.5 (2)	S1—O3—C7—C8	103.2 (3)
O2—S1—O3—C7	52.5 (2)	C14—O4—C8—C9	8.8 (5)
C1—S1—O3—C7	−63.8 (2)	C14—O4—C8—C7	−171.0 (3)
O1—S1—C1—C2	−163.9 (3)	C12—C7—C8—O4	−178.3 (3)
O2—S1—C1—C2	−29.4 (3)	O3—C7—C8—O4	−0.8 (4)
O3—S1—C1—C2	86.3 (3)	C12—C7—C8—C9	1.8 (5)
O1—S1—C1—C6	19.7 (3)	O3—C7—C8—C9	179.3 (3)
O2—S1—C1—C6	154.3 (3)	O4—C8—C9—C10	179.3 (3)
O3—S1—C1—C6	−90.0 (3)	C7—C8—C9—C10	−0.8 (5)
C6—C1—C2—C3	1.0 (6)	C8—C9—C10—C11	1.0 (6)
S1—C1—C2—C3	−175.2 (3)	C9—C10—C11—C12	−2.1 (6)
C1—C2—C3—C4	−0.4 (6)	C9—C10—C11—C13	179.8 (3)
C2—C3—C4—C5	−0.1 (7)	C8—C7—C12—C11	−2.9 (5)
C3—C4—C5—C6	0.1 (8)	O3—C7—C12—C11	179.6 (3)
C2—C1—C6—C5	−1.1 (6)	C10—C11—C12—C7	3.0 (5)
S1—C1—C6—C5	175.2 (3)	C13—C11—C12—C7	−178.9 (3)
C4—C5—C6—C1	0.5 (7)	C10—C11—C13—O5	−5.0 (7)
S1—O3—C7—C12	−79.3 (3)	C12—C11—C13—O5	176.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O5^i	0.93	2.56	3.405 (6)	151

Symmetry code: (i) x, y, z+1.