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The title compound, C13H15BrO3, was synthesized by the reaction of ethyl 3-(2,3-dihydro-1-benzofuran-5-yl)propano­ate with bromine. The benzofuran system is planar and subtends an angle of 87.27 (9)° with the propanoate unit.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807005077/sj2216sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807005077/sj2216Isup2.hkl
Contains datablock I

CCDC reference: 640490

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.022
  • wR factor = 0.053
  • Data-to-parameter ratio = 10.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.94 PLAT301_ALERT_3_C Main Residue Disorder ......................... 11.00 Perc. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 18.80 Deg. C12 -O3 -C12' 1.555 1.555 1.555
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.940 Tmax scaled 0.555 Tmin scaled 0.454 REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.01 From the CIF: _reflns_number_total 1862 Count of symmetry unique reflns 1202 Completeness (_total/calc) 154.91% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 660 Fraction of Friedel pairs measured 0.549 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 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 2 ALERT type 3 Indicator that the structure quality may be low 2 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, 2001); data reduction: SAINT; 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: SHELXTL.

thyl 3-(7-bromo-2,3-dihydro-1-benzofuran-5-yl)propanoate top
Crystal data top
C13H15BrO3F(000) = 608
Mr = 299.16Dx = 1.585 Mg m3
Monoclinic, C2Melting point: 321 K
Hall symbol: C 2yMo Kα radiation, λ = 0.71073 Å
a = 16.779 (4) ÅCell parameters from 2426 reflections
b = 7.2732 (14) Åθ = 2.5–26.4°
c = 10.636 (2) ŵ = 3.27 mm1
β = 104.952 (4)°T = 294 K
V = 1254.0 (5) Å3Block, colorless
Z = 40.26 × 0.20 × 0.18 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
1862 independent reflections
Radiation source: fine-focus sealed tube1749 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1998)
h = 1917
Tmin = 0.483, Tmax = 0.591k = 84
3242 measured reflectionsl = 1212
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.022H-atom parameters constrained
wR(F2) = 0.053 w = 1/[σ2(Fo2) + (0.0151P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
1862 reflectionsΔρmax = 0.28 e Å3
172 parametersΔρmin = 0.30 e Å3
65 restraintsAbsolute structure: Flack (1983), 662 Friedel Pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.011 (9)
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
xyzUiso*/UeqOcc. (<1)
Br10.564027 (15)0.36149 (6)0.88065 (3)0.05199 (11)
O10.56792 (13)0.7475 (3)0.7520 (2)0.0478 (5)
O20.87606 (14)0.3621 (4)0.63848 (18)0.0610 (5)
O30.86836 (15)0.0613 (3)0.6681 (2)0.0528 (5)
C10.73361 (17)0.4220 (4)0.8906 (3)0.0354 (7)
H1A0.74240.30890.93270.043*
C20.65492 (16)0.4935 (4)0.8531 (2)0.0352 (6)
C30.64263 (16)0.6622 (4)0.7945 (2)0.0341 (6)
C40.5828 (2)0.9140 (4)0.6859 (4)0.0557 (9)
H4A0.55951.01930.71970.067*
H4B0.55690.90440.59340.067*
C50.6740 (2)0.9374 (4)0.7084 (4)0.0530 (9)
H5A0.69391.04120.76510.064*
H5B0.68900.95460.62710.064*
C60.70739 (19)0.7597 (4)0.7722 (3)0.0375 (7)
C70.78603 (17)0.6874 (4)0.8070 (2)0.0370 (6)
H7A0.82980.75330.79070.044*
C80.79959 (16)0.5165 (4)0.8661 (2)0.0352 (6)
C90.8847 (2)0.4337 (4)0.9054 (3)0.0434 (7)
H9A0.92230.51430.87590.052*
H9B0.90260.42920.99960.052*
C100.89142 (19)0.2439 (4)0.8530 (3)0.0389 (7)
H10A0.94600.19580.89310.047*
H10B0.85170.16470.87830.047*
C110.87696 (17)0.2353 (4)0.7078 (3)0.0395 (6)
C120.8455 (10)0.013 (2)0.5309 (10)0.063 (4)0.35
H12A0.85400.11610.47800.075*0.35
H12B0.78820.02440.50330.075*0.35
C130.9028 (8)0.148 (3)0.5198 (16)0.083 (4)0.35
H13A0.90190.16630.43010.124*0.35
H13B0.88430.25730.55390.124*0.35
H13C0.95810.11970.56860.124*0.35
C12'0.8721 (5)0.0378 (11)0.5338 (6)0.059 (2)0.65
H12C0.92470.08030.52280.071*0.65
H12D0.82830.10640.47520.071*0.65
C13'0.8619 (5)0.1652 (11)0.5068 (8)0.075 (2)0.65
H13D0.86110.18850.41760.112*0.65
H13E0.81100.20610.52280.112*0.65
H13F0.90710.23040.56280.112*0.65
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.04231 (16)0.04839 (16)0.0705 (2)0.00077 (18)0.02393 (12)0.00571 (19)
O10.0403 (12)0.0432 (12)0.0598 (13)0.0108 (9)0.0129 (10)0.0048 (10)
O20.0884 (15)0.0500 (11)0.0478 (10)0.014 (2)0.0234 (10)0.0126 (16)
O30.0739 (15)0.0447 (11)0.0408 (11)0.0010 (10)0.0166 (10)0.0012 (9)
C10.0390 (16)0.0355 (15)0.0321 (14)0.0038 (10)0.0097 (12)0.0012 (10)
C20.0330 (15)0.0379 (15)0.0371 (14)0.0012 (11)0.0138 (11)0.0039 (12)
C30.0337 (15)0.0355 (14)0.0305 (13)0.0081 (11)0.0034 (11)0.0027 (11)
C40.054 (2)0.049 (2)0.061 (2)0.0131 (13)0.0092 (17)0.0080 (14)
C50.055 (2)0.0404 (16)0.060 (2)0.0029 (14)0.0090 (17)0.0089 (15)
C60.0460 (19)0.0328 (15)0.0335 (16)0.0007 (13)0.0099 (13)0.0025 (12)
C70.0359 (16)0.0380 (15)0.0385 (15)0.0015 (11)0.0121 (12)0.0022 (12)
C80.0351 (14)0.0402 (15)0.0286 (13)0.0034 (11)0.0055 (11)0.0054 (11)
C90.0331 (17)0.0514 (17)0.0432 (17)0.0034 (12)0.0052 (13)0.0020 (14)
C100.0374 (16)0.0407 (17)0.0383 (16)0.0096 (13)0.0091 (13)0.0059 (13)
C110.0341 (15)0.0443 (17)0.0407 (16)0.0079 (13)0.0108 (12)0.0034 (14)
C120.079 (7)0.063 (5)0.048 (5)0.016 (5)0.019 (5)0.007 (4)
C130.087 (7)0.094 (6)0.070 (6)0.017 (7)0.024 (6)0.009 (6)
C12'0.079 (5)0.060 (4)0.040 (3)0.014 (3)0.020 (3)0.007 (2)
C13'0.100 (5)0.067 (4)0.059 (3)0.014 (4)0.025 (4)0.020 (3)
Geometric parameters (Å, º) top
Br1—C21.888 (3)C7—H7A0.9300
O1—C31.367 (3)C8—C91.507 (4)
O1—C41.454 (4)C9—C101.504 (4)
O2—C111.178 (4)C9—H9A0.9700
O3—C111.330 (4)C9—H9B0.9700
O3—C121.453 (9)C10—C111.502 (4)
O3—C12'1.457 (6)C10—H10A0.9700
C1—C21.379 (4)C10—H10B0.9700
C1—C81.384 (4)C12—C131.537 (10)
C1—H1A0.9300C12—H12A0.9700
C2—C31.367 (4)C12—H12B0.9700
C3—C61.368 (4)C13—H13A0.9600
C4—C51.497 (5)C13—H13B0.9600
C4—H4A0.9700C13—H13C0.9600
C4—H4B0.9700C12'—C13'1.505 (8)
C5—C61.500 (4)C12'—H12C0.9700
C5—H5A0.9700C12'—H12D0.9700
C5—H5B0.9700C13'—H13D0.9600
C6—C71.379 (4)C13'—H13E0.9600
C7—C81.385 (4)C13'—H13F0.9600
C3—O1—C4106.3 (2)C10—C9—H9B108.6
C11—O3—C12121.8 (8)C8—C9—H9B108.6
C11—O3—C12'113.2 (4)H9A—C9—H9B107.5
C12—O3—C12'18.8 (8)C11—C10—C9114.3 (3)
C2—C1—C8120.7 (2)C11—C10—H10A108.7
C2—C1—H1A119.6C9—C10—H10A108.7
C8—C1—H1A119.6C11—C10—H10B108.7
C3—C2—C1119.4 (2)C9—C10—H10B108.7
C3—C2—Br1119.6 (2)H10A—C10—H10B107.6
C1—C2—Br1121.0 (2)O2—C11—O3124.3 (3)
O1—C3—C2125.1 (2)O2—C11—C10125.7 (3)
O1—C3—C6114.2 (2)O3—C11—C10109.9 (3)
C2—C3—C6120.7 (2)O3—C12—C13104.6 (11)
O1—C4—C5108.2 (3)O3—C12—H12A110.8
O1—C4—H4A110.1C13—C12—H12A110.8
C5—C4—H4A110.1O3—C12—H12B110.8
O1—C4—H4B110.1C13—C12—H12B110.8
C5—C4—H4B110.1H12A—C12—H12B108.9
H4A—C4—H4B108.4C12—C13—H13A109.5
C4—C5—C6102.8 (3)C12—C13—H13B109.5
C4—C5—H5A111.2H13A—C13—H13B109.5
C6—C5—H5A111.2C12—C13—H13C109.5
C4—C5—H5B111.2H13A—C13—H13C109.5
C6—C5—H5B111.2H13B—C13—H13C109.5
H5A—C5—H5B109.1O3—C12'—C13'105.7 (6)
C3—C6—C7120.2 (3)O3—C12'—H12C110.6
C3—C6—C5107.7 (3)C13'—C12'—H12C110.6
C7—C6—C5132.1 (3)O3—C12'—H12D110.6
C6—C7—C8119.8 (3)C13'—C12'—H12D110.6
C6—C7—H7A120.1H12C—C12'—H12D108.7
C8—C7—H7A120.1C12'—C13'—H13D109.5
C1—C8—C7119.0 (2)C12'—C13'—H13E109.5
C1—C8—C9119.8 (3)H13D—C13'—H13E109.5
C7—C8—C9121.1 (3)C12'—C13'—H13F109.5
C10—C9—C8114.8 (3)H13D—C13'—H13F109.5
C10—C9—H9A108.6H13E—C13'—H13F109.5
C8—C9—H9A108.6
C8—C1—C2—C31.9 (4)C2—C1—C8—C72.0 (4)
C8—C1—C2—Br1177.8 (2)C2—C1—C8—C9178.7 (3)
C4—O1—C3—C2174.8 (3)C6—C7—C8—C10.7 (4)
C4—O1—C3—C64.3 (3)C6—C7—C8—C9180.0 (3)
C1—C2—C3—O1179.4 (2)C1—C8—C9—C1054.6 (4)
Br1—C2—C3—O10.3 (4)C7—C8—C9—C10126.1 (3)
C1—C2—C3—C60.4 (4)C8—C9—C10—C1166.4 (4)
Br1—C2—C3—C6179.3 (2)C12—O3—C11—O28.6 (9)
C3—O1—C4—C58.2 (3)C12'—O3—C11—O210.2 (6)
O1—C4—C5—C68.6 (3)C12—O3—C11—C10173.8 (8)
O1—C3—C6—C7178.2 (2)C12'—O3—C11—C10167.4 (4)
C2—C3—C6—C70.9 (4)C9—C10—C11—O214.3 (4)
O1—C3—C6—C51.3 (3)C9—C10—C11—O3168.1 (3)
C2—C3—C6—C5179.5 (2)C11—O3—C12—C13136.4 (9)
C4—C5—C6—C36.1 (3)C12'—O3—C12—C1369 (3)
C4—C5—C6—C7173.3 (3)C11—O3—C12'—C13'179.6 (5)
C3—C6—C7—C80.8 (4)C12—O3—C12'—C13'59 (3)
C5—C6—C7—C8179.8 (3)
 

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