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The mol­ecular structure of the title compound, C15H9BrO2, consists of two essentially planar units, benzopyran-1-one and 2-bromo­phenyl, which are inclined at 51.42 (12)° with respect to one another. The structure is stabilized by two weak inter­molecular C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806024998/lh2111sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806024998/lh2111Isup2.hkl
Contains datablock I

CCDC reference: 618264

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.038
  • wR factor = 0.094
  • Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.536 From the CIF: _refine_ls_abs_structure_Flack_su 0.017 PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 0.54
Alert level G 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 27.50 From the CIF: _reflns_number_total 2492 Count of symmetry unique reflns 1454 Completeness (_total/calc) 171.39% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1038 Fraction of Friedel pairs measured 0.714 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

3-(2-Bromophenyl)isocoumarin top
Crystal data top
C15H9BrO2F(000) = 600
Mr = 301.13Dx = 1.701 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 2492 reflections
a = 12.595 (6) Åθ = 3.4–27.5°
b = 12.128 (9) ŵ = 3.48 mm1
c = 7.699 (6) ÅT = 173 K
V = 1176.0 (14) Å3Block, colorless
Z = 40.16 × 0.14 × 0.10 mm
Data collection top
Bruker–Nonius KappaCCD
diffractometer
7105 independent reflections
Radiation source: fine-focus sealed tube2096 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
ω and φ scansθmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
h = 1615
Tmin = 0.594, Tmax = 0.708k = 1515
2492 measured reflectionsl = 99
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)] = 0.038H-atom parameters constrained
wR(F2) = 0.094 w = 1/[σ2(Fo2) + (0.0492P)2 + 0.803P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
2492 reflectionsΔρmax = 0.37 e Å3
164 parametersΔρmin = 0.50 e Å3
1 restraintAbsolute structure: Flack (1983), 1073 Fridels
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.536 (17)
Special details top

Experimental. EI–MS m/z (%): 303, 301 (M+, 30), 165?(28), 137 (19.8), 117?(100); IR (film, ν, cm-1): 2913, 2849, 1712, 1694, 1598, 1572, 1471, 1151, 832 cm-1; 1H NMR (CDCl3): δ 6.90 (s, 1H, H-4), 7.43 (m, 1H, H-5), 7.47 (m, 1H, H-7), 7.49 (m, 1H, H-4'), 7.51 (m, 1H, H-6'), 7.69 (dt, J = 7.2, 1.8 Hz, 1H, H-6); 7.81 (dt, J = 7.8, 1.7 Hz, 1H, H-5').

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.54430 (3)0.73308 (3)0.79476 (12)0.03527 (14)
O10.4843 (2)0.3883 (2)0.7077 (4)0.0284 (6)
O20.3909 (2)0.24387 (19)0.7917 (10)0.0367 (6)
C10.3881 (3)0.3320 (3)0.7239 (6)0.0324 (10)
C20.2941 (3)0.3891 (3)0.6602 (6)0.0282 (9)
C30.1939 (3)0.3388 (4)0.6767 (6)0.0333 (9)
H30.18770.26840.72980.040*
C40.1049 (3)0.3923 (4)0.6156 (6)0.0408 (11)
H40.03710.35900.62860.049*
C50.1133 (4)0.4932 (4)0.5362 (6)0.0407 (12)
H50.05140.52790.49180.049*
C60.2118 (4)0.5460 (4)0.5195 (7)0.0306 (12)
H60.21680.61610.46480.037*
C70.3026 (3)0.4941 (4)0.5847 (6)0.0292 (10)
C80.4055 (3)0.5443 (3)0.5733 (5)0.0268 (9)
H80.41300.61510.52190.032*
C90.4909 (3)0.4918 (3)0.6346 (5)0.0256 (8)
C100.6035 (3)0.5289 (3)0.6275 (5)0.0261 (8)
C110.6799 (4)0.4572 (4)0.5590 (6)0.0330 (10)
H110.65830.38650.51920.040*
C120.7865 (4)0.4862 (5)0.5475 (7)0.0369 (14)
H120.83700.43660.50000.044*
C130.8172 (3)0.5889 (4)0.6067 (6)0.0366 (10)
H130.88950.61030.59780.044*
C140.7440 (3)0.6617 (4)0.6790 (6)0.0326 (9)
H140.76600.73150.72190.039*
C150.6384 (3)0.6301 (3)0.6871 (5)0.0291 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0370 (2)0.02679 (19)0.0420 (2)0.00065 (13)0.0000 (3)0.0036 (4)
O10.0314 (14)0.0205 (13)0.0335 (15)0.0020 (11)0.0018 (12)0.0019 (12)
O20.0421 (14)0.0243 (13)0.0436 (14)0.0046 (9)0.001 (3)0.005 (2)
C10.035 (2)0.027 (2)0.035 (2)0.0050 (16)0.0053 (17)0.0077 (17)
C20.032 (2)0.0235 (19)0.029 (2)0.0019 (15)0.0018 (16)0.0073 (17)
C30.039 (2)0.029 (2)0.032 (2)0.0099 (17)0.0071 (18)0.0055 (18)
C40.033 (2)0.044 (3)0.045 (3)0.013 (2)0.009 (2)0.018 (2)
C50.022 (2)0.051 (3)0.049 (3)0.0024 (19)0.0008 (19)0.012 (2)
C60.026 (2)0.031 (3)0.035 (3)0.0019 (18)0.0024 (18)0.003 (2)
C70.030 (2)0.030 (2)0.028 (2)0.0022 (18)0.0008 (17)0.0052 (19)
C80.026 (2)0.0233 (19)0.031 (2)0.0008 (15)0.0028 (16)0.0023 (17)
C90.031 (2)0.0196 (17)0.026 (2)0.0011 (15)0.0002 (16)0.0003 (15)
C100.025 (2)0.0248 (19)0.028 (2)0.0009 (15)0.0051 (16)0.0042 (17)
C110.035 (2)0.029 (2)0.035 (3)0.0034 (19)0.0011 (19)0.0020 (19)
C120.035 (3)0.041 (3)0.035 (3)0.006 (2)0.003 (2)0.002 (2)
C130.027 (2)0.041 (3)0.041 (3)0.0020 (18)0.0012 (19)0.004 (2)
C140.033 (2)0.029 (2)0.036 (2)0.0076 (17)0.0045 (18)0.0047 (18)
C150.031 (2)0.0251 (19)0.031 (2)0.0009 (15)0.0020 (18)0.0071 (17)
Geometric parameters (Å, º) top
Br1—C151.911 (4)C7—C81.434 (6)
O1—C91.378 (5)C8—C91.335 (6)
O1—C11.396 (5)C8—H80.9500
O2—C11.190 (6)C9—C101.488 (5)
C1—C21.457 (6)C10—C151.382 (6)
C2—C71.404 (6)C10—C111.400 (6)
C2—C31.407 (5)C11—C121.390 (6)
C3—C41.378 (6)C11—H110.9500
C3—H30.9500C12—C131.381 (8)
C4—C51.372 (7)C12—H120.9500
C4—H40.9500C13—C141.392 (7)
C5—C61.402 (7)C13—H130.9500
C5—H50.9500C14—C151.386 (6)
C6—C71.399 (6)C14—H140.9500
C6—H60.9500
C9—O1—C1122.3 (3)C9—C8—H8119.9
O2—C1—O1116.9 (4)C7—C8—H8119.9
O2—C1—C2126.8 (4)C8—C9—O1122.0 (4)
O1—C1—C2116.3 (4)C8—C9—C10127.6 (4)
C7—C2—C3119.9 (4)O1—C9—C10110.3 (3)
C7—C2—C1120.6 (4)C15—C10—C11117.3 (4)
C3—C2—C1119.5 (4)C15—C10—C9123.9 (4)
C4—C3—C2119.6 (4)C11—C10—C9118.8 (4)
C4—C3—H3120.2C12—C11—C10122.0 (5)
C2—C3—H3120.2C12—C11—H11119.0
C5—C4—C3120.6 (4)C10—C11—H11119.0
C5—C4—H4119.7C13—C12—C11118.5 (5)
C3—C4—H4119.7C13—C12—H12120.7
C4—C5—C6121.1 (5)C11—C12—H12120.7
C4—C5—H5119.5C12—C13—C14121.2 (4)
C6—C5—H5119.5C12—C13—H13119.4
C7—C6—C5119.0 (5)C14—C13—H13119.4
C7—C6—H6120.5C15—C14—C13118.6 (4)
C5—C6—H6120.5C15—C14—H14120.7
C6—C7—C2119.6 (4)C13—C14—H14120.7
C6—C7—C8121.7 (4)C10—C15—C14122.4 (4)
C2—C7—C8118.6 (4)C10—C15—Br1121.8 (3)
C9—C8—C7120.3 (4)C14—C15—Br1115.7 (3)
C9—O1—C1—O2178.7 (5)C7—C8—C9—O11.0 (6)
C9—O1—C1—C20.5 (5)C7—C8—C9—C10177.3 (4)
O2—C1—C2—C7179.1 (6)C1—O1—C9—C80.6 (6)
O1—C1—C2—C71.0 (6)C1—O1—C9—C10177.4 (3)
O2—C1—C2—C30.1 (8)C8—C9—C10—C1553.5 (6)
O1—C1—C2—C3178.1 (4)O1—C9—C10—C15129.9 (4)
C7—C2—C3—C41.2 (6)C8—C9—C10—C11127.4 (5)
C1—C2—C3—C4179.6 (4)O1—C9—C10—C1149.1 (5)
C2—C3—C4—C51.1 (7)C15—C10—C11—C121.2 (7)
C3—C4—C5—C61.9 (7)C9—C10—C11—C12179.7 (4)
C4—C5—C6—C70.3 (7)C10—C11—C12—C130.4 (7)
C5—C6—C7—C22.0 (7)C11—C12—C13—C141.0 (8)
C5—C6—C7—C8179.3 (5)C12—C13—C14—C151.5 (7)
C3—C2—C7—C62.8 (6)C11—C10—C15—C140.7 (6)
C1—C2—C7—C6178.1 (4)C9—C10—C15—C14179.7 (4)
C3—C2—C7—C8178.6 (4)C11—C10—C15—Br1176.7 (3)
C1—C2—C7—C80.6 (6)C9—C10—C15—Br12.3 (6)
C6—C7—C8—C9179.1 (4)C13—C14—C15—C100.6 (6)
C2—C7—C8—C90.4 (6)C13—C14—C15—Br1178.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O2i0.952.553.439 (6)155
C6—H6···O2ii0.952.453.242 (7)140
Symmetry codes: (i) x1/2, y+1/2, z; (ii) x+1/2, y+1/2, z1/2.
 

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