Download citation
Download citation
link to html
In the title compound, C15H13BrO5S, the o-vanillin group makes a dihedral angle of 41.54 (9)° with the benzene ring. The crystal packing is stabilized by weak inter­molecular C—H...Br inter­actions, leading to chains of mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806047167/hb2195sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806047167/hb2195Isup2.hkl
Contains datablock I

CCDC reference: 629841

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.035
  • wR factor = 0.083
  • Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H14 .. BR1 .. 2.96 Ang.
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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

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.

4-Bromo-2-formyl-6-methoxyphenyl 4-methylbenzenesulfonate top
Crystal data top
C15H13BrO5SZ = 2
Mr = 385.22F(000) = 388
Triclinic, P1Dx = 1.686 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.752 (3) ÅCell parameters from 1640 reflections
b = 9.025 (4) Åθ = 3.2–25.2°
c = 11.638 (5) ŵ = 2.87 mm1
α = 71.559 (7)°T = 294 K
β = 87.746 (7)°Block, colorless
γ = 79.326 (7)°0.24 × 0.20 × 0.14 mm
V = 758.9 (6) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2662 independent reflections
Radiation source: fine-focus sealed tube1991 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.485, Tmax = 0.669k = 710
3898 measured reflectionsl = 1313
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.033P)2 + 0.3049P]
where P = (Fo2 + 2Fc2)/3
2662 reflections(Δ/σ)max < 0.001
201 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.35 e Å3
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
xyzUiso*/Ueq
Br10.24915 (6)0.59300 (5)0.02244 (4)0.06783 (17)
S10.26176 (11)1.14836 (9)0.27853 (7)0.0426 (2)
O10.1719 (3)1.2747 (3)0.3174 (2)0.0574 (6)
O20.4044 (3)1.1692 (3)0.1988 (2)0.0520 (6)
O30.1087 (3)1.1083 (2)0.20976 (19)0.0413 (5)
O40.0327 (3)0.8274 (2)0.32560 (19)0.0484 (6)
O50.3183 (4)1.2081 (3)0.1271 (2)0.0759 (8)
C10.3219 (4)0.9776 (4)0.4008 (3)0.0388 (7)
C20.2332 (4)0.9592 (4)0.5081 (3)0.0447 (8)
H20.14431.03970.51630.054*
C30.2767 (4)0.8219 (4)0.6023 (3)0.0477 (8)
H30.21710.81020.67460.057*
C40.4074 (4)0.6998 (4)0.5923 (3)0.0423 (8)
C50.4955 (4)0.7229 (4)0.4845 (3)0.0455 (8)
H50.58560.64310.47670.055*
C60.4551 (4)0.8593 (4)0.3886 (3)0.0440 (8)
H60.51620.87190.31680.053*
C70.4558 (5)0.5504 (4)0.6954 (3)0.0615 (10)
H7A0.54050.47610.66940.092*
H7B0.35290.50520.72250.092*
H7C0.50530.57360.76070.092*
C80.1507 (4)0.9893 (3)0.1554 (3)0.0349 (7)
C90.1071 (4)0.8423 (3)0.2166 (3)0.0363 (7)
C100.1406 (4)0.7244 (4)0.1629 (3)0.0384 (7)
H100.11460.62450.20290.046*
C110.2124 (4)0.7553 (4)0.0501 (3)0.0397 (7)
C120.2532 (4)0.9001 (4)0.0123 (3)0.0418 (8)
H120.30180.91800.08870.050*
C130.2204 (4)1.0195 (3)0.0409 (3)0.0370 (7)
C140.2518 (4)1.1798 (4)0.0302 (3)0.0497 (8)
H140.21811.26230.00230.060*
C150.0014 (6)0.6751 (4)0.3936 (3)0.0664 (11)
H15A0.08430.64520.34980.100*
H15B0.04900.67840.47030.100*
H15C0.10590.59870.40650.100*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0931 (3)0.0506 (2)0.0649 (3)0.0097 (2)0.0115 (2)0.0284 (2)
S10.0507 (5)0.0346 (4)0.0433 (5)0.0116 (4)0.0000 (4)0.0111 (4)
O10.0762 (17)0.0375 (13)0.0612 (16)0.0074 (12)0.0015 (13)0.0206 (12)
O20.0559 (14)0.0525 (14)0.0490 (14)0.0253 (12)0.0066 (11)0.0098 (11)
O30.0429 (12)0.0339 (12)0.0457 (13)0.0049 (10)0.0020 (10)0.0116 (10)
O40.0621 (15)0.0406 (12)0.0425 (13)0.0190 (11)0.0147 (11)0.0092 (10)
O50.094 (2)0.0685 (18)0.0557 (18)0.0361 (16)0.0186 (16)0.0033 (14)
C10.0411 (18)0.0384 (18)0.0371 (18)0.0085 (14)0.0020 (14)0.0112 (14)
C20.0449 (19)0.0459 (19)0.045 (2)0.0030 (16)0.0015 (16)0.0197 (16)
C30.052 (2)0.059 (2)0.0361 (19)0.0148 (18)0.0081 (16)0.0182 (17)
C40.050 (2)0.0403 (18)0.0399 (19)0.0123 (16)0.0028 (15)0.0144 (15)
C50.0453 (19)0.0411 (19)0.048 (2)0.0004 (15)0.0011 (16)0.0144 (16)
C60.0431 (19)0.050 (2)0.0410 (19)0.0085 (16)0.0061 (15)0.0173 (16)
C70.089 (3)0.046 (2)0.047 (2)0.014 (2)0.004 (2)0.0091 (17)
C80.0354 (17)0.0301 (16)0.0365 (18)0.0051 (13)0.0043 (13)0.0066 (13)
C90.0354 (17)0.0360 (17)0.0341 (17)0.0075 (14)0.0004 (13)0.0058 (14)
C100.0400 (17)0.0295 (16)0.0413 (19)0.0098 (14)0.0011 (14)0.0028 (14)
C110.0383 (18)0.0356 (18)0.0414 (19)0.0017 (14)0.0027 (14)0.0092 (14)
C120.0405 (18)0.047 (2)0.0357 (18)0.0077 (15)0.0002 (14)0.0102 (15)
C130.0344 (17)0.0340 (17)0.0373 (18)0.0078 (14)0.0057 (14)0.0020 (14)
C140.056 (2)0.044 (2)0.044 (2)0.0189 (17)0.0059 (17)0.0021 (16)
C150.095 (3)0.048 (2)0.052 (2)0.026 (2)0.030 (2)0.0062 (18)
Geometric parameters (Å, º) top
Br1—C111.884 (3)C5—H50.9300
S1—O11.413 (2)C6—H60.9300
S1—O21.416 (2)C7—H7A0.9600
S1—O31.611 (2)C7—H7B0.9600
S1—C11.737 (3)C7—H7C0.9600
O3—C81.394 (3)C8—C131.382 (4)
O4—C91.350 (3)C8—C91.389 (4)
O4—C151.419 (4)C9—C101.377 (4)
O5—C141.193 (4)C10—C111.371 (4)
C1—C61.379 (4)C10—H100.9300
C1—C21.380 (4)C11—C121.367 (4)
C2—C31.365 (5)C12—C131.384 (4)
C2—H20.9300C12—H120.9300
C3—C41.383 (4)C13—C141.481 (4)
C3—H30.9300C14—H140.9300
C4—C51.379 (4)C15—H15A0.9600
C4—C71.491 (5)C15—H15B0.9600
C5—C61.369 (5)C15—H15C0.9600
O1—S1—O2120.92 (15)H7A—C7—H7C109.5
O1—S1—O3102.48 (13)H7B—C7—H7C109.5
O2—S1—O3107.51 (13)C13—C8—C9121.0 (3)
O1—S1—C1110.99 (15)C13—C8—O3121.4 (2)
O2—S1—C1109.28 (15)C9—C8—O3117.4 (3)
O3—S1—C1104.08 (13)O4—C9—C10124.9 (3)
C8—O3—S1118.90 (17)O4—C9—C8116.3 (3)
C9—O4—C15117.3 (2)C10—C9—C8118.8 (3)
C6—C1—C2120.5 (3)C11—C10—C9119.5 (3)
C6—C1—S1119.6 (2)C11—C10—H10120.2
C2—C1—S1119.9 (2)C9—C10—H10120.2
C3—C2—C1119.5 (3)C12—C11—C10122.5 (3)
C3—C2—H2120.2C12—C11—Br1119.3 (2)
C1—C2—H2120.2C10—C11—Br1118.2 (2)
C2—C3—C4121.4 (3)C11—C12—C13118.5 (3)
C2—C3—H3119.3C11—C12—H12120.7
C4—C3—H3119.3C13—C12—H12120.7
C5—C4—C3117.6 (3)C8—C13—C12119.7 (3)
C5—C4—C7121.0 (3)C8—C13—C14121.6 (3)
C3—C4—C7121.4 (3)C12—C13—C14118.6 (3)
C6—C5—C4122.3 (3)O5—C14—C13123.2 (3)
C6—C5—H5118.8O5—C14—H14118.4
C4—C5—H5118.8C13—C14—H14118.4
C5—C6—C1118.6 (3)O4—C15—H15A109.5
C5—C6—H6120.7O4—C15—H15B109.5
C1—C6—H6120.7H15A—C15—H15B109.5
C4—C7—H7A109.5O4—C15—H15C109.5
C4—C7—H7B109.5H15A—C15—H15C109.5
H7A—C7—H7B109.5H15B—C15—H15C109.5
C4—C7—H7C109.5
O1—S1—O3—C8178.3 (2)C15—O4—C9—C104.9 (4)
O2—S1—O3—C849.9 (2)C15—O4—C9—C8175.6 (3)
C1—S1—O3—C866.0 (2)C13—C8—C9—O4177.2 (3)
O1—S1—C1—C6159.4 (2)O3—C8—C9—O42.1 (4)
O2—S1—C1—C623.6 (3)C13—C8—C9—C102.3 (4)
O3—S1—C1—C691.0 (3)O3—C8—C9—C10177.4 (2)
O1—S1—C1—C222.4 (3)O4—C9—C10—C11178.2 (3)
O2—S1—C1—C2158.2 (2)C8—C9—C10—C111.3 (4)
O3—S1—C1—C287.2 (3)C9—C10—C11—C120.1 (5)
C6—C1—C2—C30.8 (5)C9—C10—C11—Br1178.0 (2)
S1—C1—C2—C3177.4 (3)C10—C11—C12—C130.0 (5)
C1—C2—C3—C40.4 (5)Br1—C11—C12—C13178.1 (2)
C2—C3—C4—C51.5 (5)C9—C8—C13—C122.2 (4)
C2—C3—C4—C7179.5 (3)O3—C8—C13—C12177.1 (3)
C3—C4—C5—C61.4 (5)C9—C8—C13—C14174.1 (3)
C7—C4—C5—C6179.4 (3)O3—C8—C13—C140.8 (4)
C4—C5—C6—C10.2 (5)C11—C12—C13—C81.0 (4)
C2—C1—C6—C50.9 (5)C11—C12—C13—C14175.4 (3)
S1—C1—C6—C5177.3 (2)C8—C13—C14—O5176.9 (3)
S1—O3—C8—C1383.0 (3)C12—C13—C14—O56.7 (5)
S1—O3—C8—C9101.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14···Br1i0.932.963.755 (4)144
Symmetry code: (i) x, y+1, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds