4-Bromo-2-formyl-6-methoxy­phenyl 4-methyl­benzene­sulfonate

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.

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

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

Crystal data

C15H13BrO5S	Z = 2
Mr = 385.22	F(000) = 388
Triclinic, P1	Dx = 1.686 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.752 (3) Å	Cell parameters from 1640 reflections
b = 9.025 (4) Å	θ = 3.2–25.2°
c = 11.638 (5) Å	µ = 2.87 mm^−1
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) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2662 independent reflections
Radiation source: fine-focus sealed tube	1991 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.485, Tmax = 0.669	k = −7→10
3898 measured reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.083	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.033P)^2 + 0.3049P] where P = (Fo^2 + 2Fc^2)/3
2662 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

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
Br1	0.24915 (6)	0.59300 (5)	−0.02244 (4)	0.06783 (17)
S1	0.26176 (11)	1.14836 (9)	0.27853 (7)	0.0426 (2)
O1	0.1719 (3)	1.2747 (3)	0.3174 (2)	0.0574 (6)
O2	0.4044 (3)	1.1692 (3)	0.1988 (2)	0.0520 (6)
O3	0.1087 (3)	1.1083 (2)	0.20976 (19)	0.0413 (5)
O4	0.0327 (3)	0.8274 (2)	0.32560 (19)	0.0484 (6)
O5	0.3183 (4)	1.2081 (3)	−0.1271 (2)	0.0759 (8)
C1	0.3219 (4)	0.9776 (4)	0.4008 (3)	0.0388 (7)
C2	0.2332 (4)	0.9592 (4)	0.5081 (3)	0.0447 (8)
H2	0.1443	1.0397	0.5163	0.054*
C3	0.2767 (4)	0.8219 (4)	0.6023 (3)	0.0477 (8)
H3	0.2171	0.8102	0.6746	0.057*
C4	0.4074 (4)	0.6998 (4)	0.5923 (3)	0.0423 (8)
C5	0.4955 (4)	0.7229 (4)	0.4845 (3)	0.0455 (8)
H5	0.5856	0.6431	0.4767	0.055*
C6	0.4551 (4)	0.8593 (4)	0.3886 (3)	0.0440 (8)
H6	0.5162	0.8719	0.3168	0.053*
C7	0.4558 (5)	0.5504 (4)	0.6954 (3)	0.0615 (10)
H7A	0.5405	0.4761	0.6694	0.092*
H7B	0.3529	0.5052	0.7225	0.092*
H7C	0.5053	0.5736	0.7607	0.092*
C8	0.1507 (4)	0.9893 (3)	0.1554 (3)	0.0349 (7)
C9	0.1071 (4)	0.8423 (3)	0.2166 (3)	0.0363 (7)
C10	0.1406 (4)	0.7244 (4)	0.1629 (3)	0.0384 (7)
H10	0.1146	0.6245	0.2029	0.046*
C11	0.2124 (4)	0.7553 (4)	0.0501 (3)	0.0397 (7)
C12	0.2532 (4)	0.9001 (4)	−0.0123 (3)	0.0418 (8)
H12	0.3018	0.9180	−0.0887	0.050*
C13	0.2204 (4)	1.0195 (3)	0.0409 (3)	0.0370 (7)
C14	0.2518 (4)	1.1798 (4)	−0.0302 (3)	0.0497 (8)
H14	0.2181	1.2623	0.0023	0.060*
C15	−0.0014 (6)	0.6751 (4)	0.3936 (3)	0.0664 (11)
H15A	−0.0843	0.6452	0.3498	0.100*
H15B	−0.0490	0.6784	0.4703	0.100*
H15C	0.1059	0.5987	0.4065	0.100*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0931 (3)	0.0506 (2)	0.0649 (3)	−0.0097 (2)	0.0115 (2)	−0.0284 (2)
S1	0.0507 (5)	0.0346 (4)	0.0433 (5)	−0.0116 (4)	0.0000 (4)	−0.0111 (4)
O1	0.0762 (17)	0.0375 (13)	0.0612 (16)	−0.0074 (12)	−0.0015 (13)	−0.0206 (12)
O2	0.0559 (14)	0.0525 (14)	0.0490 (14)	−0.0253 (12)	0.0066 (11)	−0.0098 (11)
O3	0.0429 (12)	0.0339 (12)	0.0457 (13)	−0.0049 (10)	−0.0020 (10)	−0.0116 (10)
O4	0.0621 (15)	0.0406 (12)	0.0425 (13)	−0.0190 (11)	0.0147 (11)	−0.0092 (10)
O5	0.094 (2)	0.0685 (18)	0.0557 (18)	−0.0361 (16)	0.0186 (16)	0.0033 (14)
C1	0.0411 (18)	0.0384 (18)	0.0371 (18)	−0.0085 (14)	−0.0020 (14)	−0.0112 (14)
C2	0.0449 (19)	0.0459 (19)	0.045 (2)	−0.0030 (16)	0.0015 (16)	−0.0197 (16)
C3	0.052 (2)	0.059 (2)	0.0361 (19)	−0.0148 (18)	0.0081 (16)	−0.0182 (17)
C4	0.050 (2)	0.0403 (18)	0.0399 (19)	−0.0123 (16)	−0.0028 (15)	−0.0144 (15)
C5	0.0453 (19)	0.0411 (19)	0.048 (2)	−0.0004 (15)	−0.0011 (16)	−0.0144 (16)
C6	0.0431 (19)	0.050 (2)	0.0410 (19)	−0.0085 (16)	0.0061 (15)	−0.0173 (16)
C7	0.089 (3)	0.046 (2)	0.047 (2)	−0.014 (2)	−0.004 (2)	−0.0091 (17)
C8	0.0354 (17)	0.0301 (16)	0.0365 (18)	−0.0051 (13)	−0.0043 (13)	−0.0066 (13)
C9	0.0354 (17)	0.0360 (17)	0.0341 (17)	−0.0075 (14)	0.0004 (13)	−0.0058 (14)
C10	0.0400 (17)	0.0295 (16)	0.0413 (19)	−0.0098 (14)	−0.0011 (14)	−0.0028 (14)
C11	0.0383 (18)	0.0356 (18)	0.0414 (19)	−0.0017 (14)	−0.0027 (14)	−0.0092 (14)
C12	0.0405 (18)	0.047 (2)	0.0357 (18)	−0.0077 (15)	−0.0002 (14)	−0.0102 (15)
C13	0.0344 (17)	0.0340 (17)	0.0373 (18)	−0.0078 (14)	−0.0057 (14)	−0.0020 (14)
C14	0.056 (2)	0.044 (2)	0.044 (2)	−0.0189 (17)	−0.0059 (17)	−0.0021 (16)
C15	0.095 (3)	0.048 (2)	0.052 (2)	−0.026 (2)	0.030 (2)	−0.0062 (18)

Geometric parameters (Å, º)

Br1—C11	1.884 (3)	C5—H5	0.9300
S1—O1	1.413 (2)	C6—H6	0.9300
S1—O2	1.416 (2)	C7—H7A	0.9600
S1—O3	1.611 (2)	C7—H7B	0.9600
S1—C1	1.737 (3)	C7—H7C	0.9600
O3—C8	1.394 (3)	C8—C13	1.382 (4)
O4—C9	1.350 (3)	C8—C9	1.389 (4)
O4—C15	1.419 (4)	C9—C10	1.377 (4)
O5—C14	1.193 (4)	C10—C11	1.371 (4)
C1—C6	1.379 (4)	C10—H10	0.9300
C1—C2	1.380 (4)	C11—C12	1.367 (4)
C2—C3	1.365 (5)	C12—C13	1.384 (4)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.383 (4)	C13—C14	1.481 (4)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.379 (4)	C15—H15A	0.9600
C4—C7	1.491 (5)	C15—H15B	0.9600
C5—C6	1.369 (5)	C15—H15C	0.9600
O1—S1—O2	120.92 (15)	H7A—C7—H7C	109.5
O1—S1—O3	102.48 (13)	H7B—C7—H7C	109.5
O2—S1—O3	107.51 (13)	C13—C8—C9	121.0 (3)
O1—S1—C1	110.99 (15)	C13—C8—O3	121.4 (2)
O2—S1—C1	109.28 (15)	C9—C8—O3	117.4 (3)
O3—S1—C1	104.08 (13)	O4—C9—C10	124.9 (3)
C8—O3—S1	118.90 (17)	O4—C9—C8	116.3 (3)
C9—O4—C15	117.3 (2)	C10—C9—C8	118.8 (3)
C6—C1—C2	120.5 (3)	C11—C10—C9	119.5 (3)
C6—C1—S1	119.6 (2)	C11—C10—H10	120.2
C2—C1—S1	119.9 (2)	C9—C10—H10	120.2
C3—C2—C1	119.5 (3)	C12—C11—C10	122.5 (3)
C3—C2—H2	120.2	C12—C11—Br1	119.3 (2)
C1—C2—H2	120.2	C10—C11—Br1	118.2 (2)
C2—C3—C4	121.4 (3)	C11—C12—C13	118.5 (3)
C2—C3—H3	119.3	C11—C12—H12	120.7
C4—C3—H3	119.3	C13—C12—H12	120.7
C5—C4—C3	117.6 (3)	C8—C13—C12	119.7 (3)
C5—C4—C7	121.0 (3)	C8—C13—C14	121.6 (3)
C3—C4—C7	121.4 (3)	C12—C13—C14	118.6 (3)
C6—C5—C4	122.3 (3)	O5—C14—C13	123.2 (3)
C6—C5—H5	118.8	O5—C14—H14	118.4
C4—C5—H5	118.8	C13—C14—H14	118.4
C5—C6—C1	118.6 (3)	O4—C15—H15A	109.5
C5—C6—H6	120.7	O4—C15—H15B	109.5
C1—C6—H6	120.7	H15A—C15—H15B	109.5
C4—C7—H7A	109.5	O4—C15—H15C	109.5
C4—C7—H7B	109.5	H15A—C15—H15C	109.5
H7A—C7—H7B	109.5	H15B—C15—H15C	109.5
C4—C7—H7C	109.5
O1—S1—O3—C8	178.3 (2)	C15—O4—C9—C10	4.9 (4)
O2—S1—O3—C8	49.9 (2)	C15—O4—C9—C8	−175.6 (3)
C1—S1—O3—C8	−66.0 (2)	C13—C8—C9—O4	−177.2 (3)
O1—S1—C1—C6	−159.4 (2)	O3—C8—C9—O4	−2.1 (4)
O2—S1—C1—C6	−23.6 (3)	C13—C8—C9—C10	2.3 (4)
O3—S1—C1—C6	91.0 (3)	O3—C8—C9—C10	177.4 (2)
O1—S1—C1—C2	22.4 (3)	O4—C9—C10—C11	178.2 (3)
O2—S1—C1—C2	158.2 (2)	C8—C9—C10—C11	−1.3 (4)
O3—S1—C1—C2	−87.2 (3)	C9—C10—C11—C12	0.1 (5)
C6—C1—C2—C3	−0.8 (5)	C9—C10—C11—Br1	−178.0 (2)
S1—C1—C2—C3	177.4 (3)	C10—C11—C12—C13	0.0 (5)
C1—C2—C3—C4	−0.4 (5)	Br1—C11—C12—C13	178.1 (2)
C2—C3—C4—C5	1.5 (5)	C9—C8—C13—C12	−2.2 (4)
C2—C3—C4—C7	179.5 (3)	O3—C8—C13—C12	−177.1 (3)
C3—C4—C5—C6	−1.4 (5)	C9—C8—C13—C14	174.1 (3)
C7—C4—C5—C6	−179.4 (3)	O3—C8—C13—C14	−0.8 (4)
C4—C5—C6—C1	0.2 (5)	C11—C12—C13—C8	1.0 (4)
C2—C1—C6—C5	0.9 (5)	C11—C12—C13—C14	−175.4 (3)
S1—C1—C6—C5	−177.3 (2)	C8—C13—C14—O5	176.9 (3)
S1—O3—C8—C13	−83.0 (3)	C12—C13—C14—O5	−6.7 (5)
S1—O3—C8—C9	101.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···Br1^i	0.93	2.96	3.755 (4)	144

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