The title compound, C19H18Br2O8, was synthesized in an anhydrous medium at 293 K. The five-membered ring adopts an envelope conformation. The dihedral angle between the two benzene rings is 2.6 (1)°.
Supporting information
CCDC reference: 618152
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.004 Å
- R factor = 0.032
- wR factor = 0.078
- Data-to-parameter ratio = 17.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98
PLAT431_ALERT_2_C Short Inter HL..A Contact Br2 .. O4 .. 3.07 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 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
1 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
Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: CrystalStructure.
2-Bromo-3,4,5-trimethoxybenzyl 4-bromo-7-methoxy-1,3-benzodioxole-5-carboxylate
top
Crystal data top
C19H18Br2O8 | Z = 2 |
Mr = 534.15 | F(000) = 532 |
Triclinic, P1 | Dx = 1.758 Mg m−3 |
Hall symbol: -P 1 | Melting point: 394 K |
a = 7.9131 (13) Å | Mo Kα radiation, λ = 0.71070 Å |
b = 9.5314 (15) Å | Cell parameters from 2511 reflections |
c = 13.949 (3) Å | θ = 3.3–27.5° |
α = 77.692 (12)° | µ = 4.06 mm−1 |
β = 79.132 (17)° | T = 294 K |
γ = 88.946 (18)° | Block, colourless |
V = 1009.2 (3) Å3 | 0.12 × 0.10 × 0.08 mm |
Data collection top
Rigaku Saturn diffractometer | 4595 independent reflections |
Radiation source: rotating anode | 3140 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.035 |
Detector resolution: 7.31 pixels mm-1 | θmax = 27.5°, θmin = 3.0° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (Jacobson, 1998) | k = −12→12 |
Tmin = 0.642, Tmax = 0.737 | l = −18→18 |
10738 measured reflections | |
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)] = 0.032 | H-atom parameters constrained |
wR(F2) = 0.078 | w = 1/[σ2(Fo2) + (0.0412P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.93 | (Δ/σ)max = 0.001 |
4595 reflections | Δρmax = 0.62 e Å−3 |
264 parameters | Δρmin = −0.54 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0077 (10) |
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 | |
Br1 | 0.89428 (4) | 0.44660 (3) | 0.20999 (2) | 0.05114 (11) | |
Br2 | 0.35230 (4) | −0.05540 (3) | 0.68355 (2) | 0.05472 (12) | |
O1 | 0.9501 (3) | 0.8354 (2) | 0.49618 (15) | 0.0658 (6) | |
O2 | 1.1042 (2) | 0.89345 (19) | 0.29177 (14) | 0.0553 (5) | |
O3 | 1.0836 (2) | 0.74419 (19) | 0.18312 (13) | 0.0500 (5) | |
O4 | 0.6252 (3) | 0.3351 (2) | 0.39280 (14) | 0.0808 (8) | |
O5 | 0.6642 (2) | 0.35493 (18) | 0.54297 (12) | 0.0447 (4) | |
O6 | 0.2268 (2) | −0.03688 (18) | 0.90085 (13) | 0.0485 (5) | |
O7 | 0.2976 (2) | 0.1708 (2) | 0.99717 (13) | 0.0527 (5) | |
O8 | 0.4809 (2) | 0.40863 (19) | 0.89615 (13) | 0.0515 (5) | |
C1 | 0.9234 (3) | 0.7422 (3) | 0.4391 (2) | 0.0428 (6) | |
C2 | 1.0005 (3) | 0.7758 (3) | 0.3398 (2) | 0.0418 (6) | |
C3 | 0.9867 (3) | 0.6871 (3) | 0.27606 (18) | 0.0390 (6) | |
C4 | 0.8933 (3) | 0.5604 (3) | 0.30511 (18) | 0.0369 (5) | |
C5 | 0.8083 (3) | 0.5250 (2) | 0.40572 (18) | 0.0360 (5) | |
C6 | 0.8260 (3) | 0.6148 (3) | 0.47018 (18) | 0.0411 (6) | |
H6 | 0.7706 | 0.5887 | 0.5366 | 0.049* | |
C7 | 1.1325 (4) | 0.8852 (3) | 0.1885 (2) | 0.0543 (7) | |
H7A | 1.0643 | 0.9559 | 0.1526 | 0.065* | |
H7B | 1.2529 | 0.9044 | 0.1584 | 0.065* | |
C8 | 0.8576 (4) | 0.8134 (3) | 0.5951 (2) | 0.0689 (9) | |
H8A | 0.8889 | 0.8873 | 0.6262 | 0.083* | |
H8B | 0.8844 | 0.7213 | 0.6319 | 0.083* | |
H8C | 0.7364 | 0.8168 | 0.5947 | 0.083* | |
C9 | 0.6932 (3) | 0.3955 (3) | 0.44311 (19) | 0.0428 (6) | |
C10 | 0.5669 (3) | 0.2221 (3) | 0.58386 (18) | 0.0422 (6) | |
H10A | 0.6409 | 0.1414 | 0.5764 | 0.051* | |
H10B | 0.4740 | 0.2178 | 0.5480 | 0.051* | |
C11 | 0.4940 (3) | 0.2137 (3) | 0.69313 (18) | 0.0366 (5) | |
C12 | 0.3956 (3) | 0.0936 (3) | 0.74681 (19) | 0.0392 (6) | |
C13 | 0.3287 (3) | 0.0805 (3) | 0.84821 (19) | 0.0394 (6) | |
C14 | 0.3575 (3) | 0.1877 (3) | 0.89558 (18) | 0.0402 (6) | |
C15 | 0.4564 (3) | 0.3100 (3) | 0.84238 (19) | 0.0399 (6) | |
C16 | 0.5232 (3) | 0.3215 (3) | 0.74140 (18) | 0.0385 (6) | |
H16 | 0.5882 | 0.4026 | 0.7057 | 0.046* | |
C17 | 0.3212 (4) | −0.1572 (3) | 0.9403 (2) | 0.0635 (8) | |
H17A | 0.2428 | −0.2349 | 0.9755 | 0.076* | |
H17B | 0.3868 | −0.1309 | 0.9853 | 0.076* | |
H17C | 0.3978 | −0.1869 | 0.8865 | 0.076* | |
C18 | 0.1467 (4) | 0.2458 (3) | 1.0231 (2) | 0.0612 (8) | |
H18A | 0.1133 | 0.2281 | 1.0945 | 0.073* | |
H18B | 0.0560 | 0.2136 | 0.9954 | 0.073* | |
H18C | 0.1678 | 0.3469 | 0.9970 | 0.073* | |
C19 | 0.5800 (4) | 0.5345 (3) | 0.8454 (2) | 0.0607 (8) | |
H19A | 0.5874 | 0.5948 | 0.8916 | 0.073* | |
H19B | 0.5259 | 0.5856 | 0.7926 | 0.073* | |
H19C | 0.6935 | 0.5082 | 0.8178 | 0.073* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0617 (2) | 0.05447 (19) | 0.04128 (16) | −0.00370 (13) | −0.00652 (13) | −0.02142 (13) |
Br2 | 0.0674 (2) | 0.04424 (18) | 0.05471 (19) | −0.01557 (13) | −0.00981 (15) | −0.01545 (14) |
O1 | 0.0845 (15) | 0.0579 (12) | 0.0595 (13) | −0.0271 (11) | −0.0013 (11) | −0.0307 (10) |
O2 | 0.0591 (12) | 0.0459 (11) | 0.0570 (12) | −0.0182 (9) | −0.0013 (10) | −0.0093 (9) |
O3 | 0.0539 (11) | 0.0496 (11) | 0.0415 (10) | −0.0122 (9) | 0.0002 (9) | −0.0059 (9) |
O4 | 0.1217 (19) | 0.0771 (16) | 0.0437 (12) | −0.0573 (14) | −0.0069 (12) | −0.0156 (11) |
O5 | 0.0546 (11) | 0.0445 (10) | 0.0345 (9) | −0.0157 (8) | −0.0066 (8) | −0.0072 (8) |
O6 | 0.0379 (10) | 0.0434 (10) | 0.0561 (11) | −0.0062 (8) | −0.0030 (9) | 0.0024 (9) |
O7 | 0.0507 (11) | 0.0668 (13) | 0.0363 (10) | 0.0064 (9) | −0.0026 (9) | −0.0071 (9) |
O8 | 0.0585 (12) | 0.0548 (12) | 0.0456 (11) | −0.0079 (9) | −0.0066 (9) | −0.0225 (9) |
C1 | 0.0475 (15) | 0.0405 (15) | 0.0447 (15) | −0.0052 (12) | −0.0093 (12) | −0.0175 (12) |
C2 | 0.0383 (14) | 0.0368 (14) | 0.0495 (16) | −0.0059 (11) | −0.0078 (12) | −0.0073 (12) |
C3 | 0.0367 (14) | 0.0421 (14) | 0.0380 (13) | 0.0017 (11) | −0.0077 (11) | −0.0077 (11) |
C4 | 0.0394 (14) | 0.0377 (14) | 0.0364 (13) | 0.0009 (11) | −0.0097 (11) | −0.0121 (11) |
C5 | 0.0400 (14) | 0.0338 (13) | 0.0360 (13) | −0.0021 (10) | −0.0086 (11) | −0.0101 (11) |
C6 | 0.0485 (15) | 0.0434 (15) | 0.0326 (13) | −0.0036 (12) | −0.0072 (12) | −0.0110 (11) |
C7 | 0.0538 (17) | 0.0506 (17) | 0.0524 (17) | −0.0082 (13) | −0.0051 (14) | −0.0011 (14) |
C8 | 0.095 (3) | 0.067 (2) | 0.0527 (18) | −0.0074 (18) | −0.0121 (17) | −0.0320 (16) |
C9 | 0.0540 (16) | 0.0412 (14) | 0.0340 (13) | −0.0073 (12) | −0.0057 (12) | −0.0117 (12) |
C10 | 0.0490 (15) | 0.0393 (14) | 0.0394 (14) | −0.0097 (11) | −0.0074 (12) | −0.0110 (11) |
C11 | 0.0359 (13) | 0.0372 (13) | 0.0374 (13) | 0.0005 (10) | −0.0085 (11) | −0.0079 (11) |
C12 | 0.0371 (13) | 0.0395 (14) | 0.0425 (14) | −0.0028 (11) | −0.0086 (11) | −0.0109 (12) |
C13 | 0.0328 (13) | 0.0381 (14) | 0.0443 (14) | 0.0004 (11) | −0.0074 (12) | −0.0022 (12) |
C14 | 0.0364 (13) | 0.0489 (16) | 0.0334 (13) | 0.0033 (11) | −0.0047 (11) | −0.0068 (12) |
C15 | 0.0386 (14) | 0.0422 (14) | 0.0420 (14) | 0.0025 (11) | −0.0107 (12) | −0.0132 (12) |
C16 | 0.0409 (14) | 0.0337 (13) | 0.0402 (14) | −0.0046 (11) | −0.0062 (12) | −0.0072 (11) |
C17 | 0.0605 (19) | 0.0549 (19) | 0.0636 (19) | 0.0029 (15) | −0.0084 (16) | 0.0099 (16) |
C18 | 0.0533 (18) | 0.078 (2) | 0.0471 (17) | 0.0030 (15) | 0.0055 (14) | −0.0146 (16) |
C19 | 0.0629 (19) | 0.0566 (19) | 0.070 (2) | −0.0080 (15) | −0.0122 (16) | −0.0289 (16) |
Geometric parameters (Å, º) top
Br1—C4 | 1.883 (2) | C7—H7A | 0.97 |
Br2—C12 | 1.892 (2) | C7—H7B | 0.97 |
O1—C1 | 1.356 (3) | C8—H8A | 0.96 |
O1—C8 | 1.409 (3) | C8—H8B | 0.96 |
O2—C2 | 1.373 (3) | C8—H8C | 0.96 |
O2—C7 | 1.435 (3) | C10—C11 | 1.510 (3) |
O3—C3 | 1.380 (3) | C10—H10A | 0.97 |
O3—C7 | 1.426 (3) | C10—H10B | 0.97 |
O4—C9 | 1.200 (3) | C11—C12 | 1.388 (3) |
O5—C9 | 1.340 (3) | C11—C16 | 1.388 (3) |
O5—C10 | 1.443 (3) | C12—C13 | 1.393 (3) |
O6—C13 | 1.379 (3) | C13—C14 | 1.373 (3) |
O6—C17 | 1.425 (3) | C14—C15 | 1.403 (3) |
O7—C14 | 1.382 (3) | C15—C16 | 1.389 (3) |
O7—C18 | 1.408 (3) | C16—H16 | 0.93 |
O8—C15 | 1.359 (3) | C17—H17A | 0.96 |
O8—C19 | 1.420 (3) | C17—H17B | 0.96 |
C1—C2 | 1.376 (4) | C17—H17C | 0.96 |
C1—C6 | 1.393 (3) | C18—H18A | 0.96 |
C2—C3 | 1.370 (3) | C18—H18B | 0.96 |
C3—C4 | 1.371 (3) | C18—H18C | 0.96 |
C4—C5 | 1.409 (3) | C19—H19A | 0.96 |
C5—C6 | 1.393 (3) | C19—H19B | 0.96 |
C5—C9 | 1.488 (3) | C19—H19C | 0.96 |
C6—H6 | 0.93 | | |
| | | |
C1—O1—C8 | 118.6 (2) | O5—C10—H10A | 109.8 |
C2—O2—C7 | 104.1 (2) | C11—C10—H10A | 109.8 |
C3—O3—C7 | 104.94 (19) | O5—C10—H10B | 109.8 |
C9—O5—C10 | 115.14 (19) | C11—C10—H10B | 109.8 |
C13—O6—C17 | 113.85 (19) | H10A—C10—H10B | 108.2 |
C14—O7—C18 | 114.7 (2) | C12—C11—C16 | 119.2 (2) |
C15—O8—C19 | 117.9 (2) | C12—C11—C10 | 118.7 (2) |
O1—C1—C2 | 117.1 (2) | C16—C11—C10 | 122.1 (2) |
O1—C1—C6 | 127.0 (2) | C11—C12—C13 | 120.4 (2) |
C2—C1—C6 | 116.0 (2) | C11—C12—Br2 | 120.42 (18) |
C3—C2—O2 | 111.0 (2) | C13—C12—Br2 | 119.13 (18) |
C3—C2—C1 | 122.0 (2) | C14—C13—O6 | 119.3 (2) |
O2—C2—C1 | 127.0 (2) | C14—C13—C12 | 120.2 (2) |
C2—C3—C4 | 123.2 (2) | O6—C13—C12 | 120.4 (2) |
C2—C3—O3 | 109.3 (2) | C13—C14—O7 | 119.8 (2) |
C4—C3—O3 | 127.5 (2) | C13—C14—C15 | 120.1 (2) |
C3—C4—C5 | 116.3 (2) | O7—C14—C15 | 120.0 (2) |
C3—C4—Br1 | 118.07 (18) | O8—C15—C16 | 125.0 (2) |
C5—C4—Br1 | 125.64 (18) | O8—C15—C14 | 115.8 (2) |
C6—C5—C4 | 120.0 (2) | C16—C15—C14 | 119.2 (2) |
C6—C5—C9 | 119.3 (2) | C11—C16—C15 | 120.9 (2) |
C4—C5—C9 | 120.6 (2) | C11—C16—H16 | 119.5 |
C1—C6—C5 | 122.6 (2) | C15—C16—H16 | 119.5 |
C1—C6—H6 | 118.7 | O6—C17—H17A | 109.5 |
C5—C6—H6 | 118.7 | O6—C17—H17B | 109.5 |
O3—C7—O2 | 108.1 (2) | H17A—C17—H17B | 109.5 |
O3—C7—H7A | 110.1 | O6—C17—H17C | 109.5 |
O2—C7—H7A | 110.1 | H17A—C17—H17C | 109.5 |
O3—C7—H7B | 110.1 | H17B—C17—H17C | 109.5 |
O2—C7—H7B | 110.1 | O7—C18—H18A | 109.5 |
H7A—C7—H7B | 108.4 | O7—C18—H18B | 109.5 |
O1—C8—H8A | 109.5 | H18A—C18—H18B | 109.5 |
O1—C8—H8B | 109.5 | O7—C18—H18C | 109.5 |
H8A—C8—H8B | 109.5 | H18A—C18—H18C | 109.5 |
O1—C8—H8C | 109.5 | H18B—C18—H18C | 109.5 |
H8A—C8—H8C | 109.5 | O8—C19—H19A | 109.5 |
H8B—C8—H8C | 109.5 | O8—C19—H19B | 109.5 |
O4—C9—O5 | 121.9 (2) | H19A—C19—H19B | 109.5 |
O4—C9—C5 | 125.8 (2) | O8—C19—H19C | 109.5 |
O5—C9—C5 | 112.2 (2) | H19A—C19—H19C | 109.5 |
O5—C10—C11 | 109.44 (19) | H19B—C19—H19C | 109.5 |
| | | |
C8—O1—C1—C2 | 172.8 (3) | C6—C5—C9—O5 | −20.9 (3) |
C8—O1—C1—C6 | −7.4 (4) | C4—C5—C9—O5 | 161.8 (2) |
C7—O2—C2—C3 | 9.2 (3) | C9—O5—C10—C11 | −161.5 (2) |
C7—O2—C2—C1 | −173.4 (3) | O5—C10—C11—C12 | 180.0 (2) |
O1—C1—C2—C3 | 177.9 (2) | O5—C10—C11—C16 | −0.3 (3) |
C6—C1—C2—C3 | −1.9 (4) | C16—C11—C12—C13 | −0.9 (4) |
O1—C1—C2—O2 | 0.8 (4) | C10—C11—C12—C13 | 178.8 (2) |
C6—C1—C2—O2 | −179.0 (2) | C16—C11—C12—Br2 | 179.78 (18) |
O2—C2—C3—C4 | 178.8 (2) | C10—C11—C12—Br2 | −0.5 (3) |
C1—C2—C3—C4 | 1.3 (4) | C17—O6—C13—C14 | −96.1 (3) |
O2—C2—C3—O3 | 0.6 (3) | C17—O6—C13—C12 | 86.8 (3) |
C1—C2—C3—O3 | −176.9 (2) | C11—C12—C13—C14 | 1.1 (4) |
C7—O3—C3—C2 | −10.2 (3) | Br2—C12—C13—C14 | −179.58 (18) |
C7—O3—C3—C4 | 171.7 (3) | C11—C12—C13—O6 | 178.1 (2) |
C2—C3—C4—C5 | 0.7 (4) | Br2—C12—C13—O6 | −2.5 (3) |
O3—C3—C4—C5 | 178.5 (2) | O6—C13—C14—O7 | 5.9 (3) |
C2—C3—C4—Br1 | −177.49 (19) | C12—C13—C14—O7 | −177.0 (2) |
O3—C3—C4—Br1 | 0.4 (3) | O6—C13—C14—C15 | −178.0 (2) |
C3—C4—C5—C6 | −1.8 (3) | C12—C13—C14—C15 | −0.9 (4) |
Br1—C4—C5—C6 | 176.20 (18) | C18—O7—C14—C13 | −102.2 (3) |
C3—C4—C5—C9 | 175.5 (2) | C18—O7—C14—C15 | 81.7 (3) |
Br1—C4—C5—C9 | −6.5 (3) | C19—O8—C15—C16 | 1.1 (4) |
O1—C1—C6—C5 | −179.1 (2) | C19—O8—C15—C14 | −179.8 (2) |
C2—C1—C6—C5 | 0.7 (4) | C13—C14—C15—O8 | −178.6 (2) |
C4—C5—C6—C1 | 1.1 (4) | O7—C14—C15—O8 | −2.5 (3) |
C9—C5—C6—C1 | −176.2 (2) | C13—C14—C15—C16 | 0.6 (4) |
C3—O3—C7—O2 | 15.9 (3) | O7—C14—C15—C16 | 176.6 (2) |
C2—O2—C7—O3 | −15.4 (3) | C12—C11—C16—C15 | 0.5 (4) |
C10—O5—C9—O4 | 8.8 (4) | C10—C11—C16—C15 | −179.1 (2) |
C10—O5—C9—C5 | −174.4 (2) | O8—C15—C16—C11 | 178.7 (2) |
C6—C5—C9—O4 | 155.8 (3) | C14—C15—C16—C11 | −0.4 (4) |
C4—C5—C9—O4 | −21.5 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O5 | 0.93 | 2.37 | 2.713 (3) | 101 |
C8—H8A···O2i | 0.96 | 2.59 | 3.533 (3) | 166 |
C16—H16···O5 | 0.93 | 2.37 | 2.735 (3) | 103 |
C17—H17B···O7ii | 0.96 | 2.57 | 3.287 (3) | 132 |
C17—H17C···Br2 | 0.96 | 2.93 | 3.468 (3) | 117 |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+1, −y, −z+2. |