Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compound, C10H10Br2O2, is a well known inhibitor of respiratory and photosynthetic processes. The methyl groups of the iso­propyl group assume approximately equal distances from the ring plane and maximum distances from the neighboring Br atom, possibly to avoid unfavourable steric interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801021353/ob6105sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801021353/ob6105Isup2.hkl
Contains datablock I

CCDC reference: 180797

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.024
  • wR factor = 0.064
  • Data-to-parameter ratio = 16.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 26.36 From the CIF: _reflns_number_total 2145 Count of symmetry unique reflns 1169 Completeness (_total/calc) 183.49% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 976 Fraction of Friedel pairs measured 0.835 Are heavy atom types Z>Si present yes 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.

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001) and ORTEP-32 (Farrugia, 1997).

2,5-Dibromo-3-methyl-6-isopropyl-1,4-benzoquinone top
Crystal data top
C10H10Br2O2F(000) = 624
Mr = 322.00Dx = 1.881 Mg m3
Monoclinic, CcMelting point: 343(2) K
Hall symbol: C -2ycMo Kα radiation, λ = 0.71073 Å
a = 5.4507 (2) ÅCell parameters from 15747 reflections
b = 18.5945 (9) Åθ = 0.9–27.1°
c = 11.4256 (6) ŵ = 7.10 mm1
β = 100.941 (3)°T = 295 K
V = 1136.97 (9) Å3Rod, yellow
Z = 40.54 × 0.21 × 0.12 mm
Data collection top
Nonius KappaCCD
diffractometer
2145 independent reflections
Radiation source: fine-focus sealed tube2042 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.000
φ scansθmax = 26.4°, θmin = 3.6°
Absorption correction: empirical (using intensity measurements)
(SCALEPACK; Otwinowski & Minor, 1997)
h = 55
Tmin = 0.180, Tmax = 0.426k = 2222
2145 measured reflectionsl = 1414
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.024 w = 1/[σ2(Fo2) + (0.0396P)2 + 1.0226P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.064(Δ/σ)max = 0.004
S = 1.04Δρmax = 0.53 e Å3
2145 reflectionsΔρmin = 0.34 e Å3
131 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraintsExtinction coefficient: 0.0105 (8)
Primary atom site location: structure-invariant direct methodsAbsolute structure: (Flack, 1983), 976 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.026 (12)
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*/Ueq
O10.6118 (7)0.12918 (18)0.6483 (3)0.0683 (9)
C10.5103 (7)0.09766 (19)0.7196 (3)0.0482 (7)
C20.5612 (7)0.0203 (2)0.7464 (3)0.0488 (8)
Br10.78142 (7)0.02215 (2)0.65665 (4)0.06701 (16)
C30.4630 (8)0.01686 (19)0.8259 (4)0.0489 (9)
C70.5110 (13)0.0950 (2)0.8549 (5)0.0802 (14)
H7A0.46410.12320.78380.120*
H7B0.41430.10980.91270.120*
H7C0.68540.10200.88690.120*
C40.2946 (7)0.0223 (2)0.8934 (3)0.0488 (8)
O20.1980 (7)0.0095 (2)0.9650 (3)0.0719 (9)
C50.2491 (7)0.09999 (19)0.8687 (3)0.0459 (7)
Br20.04670 (6)0.14325 (2)0.96623 (3)0.06778 (17)
C60.3369 (8)0.1366 (2)0.7847 (3)0.0480 (8)
C80.2736 (9)0.2142 (2)0.7493 (4)0.0606 (10)
H80.15310.23070.79700.073*
C90.5040 (11)0.2635 (2)0.7795 (5)0.0750 (13)
H9A0.62760.24850.73480.113*
H9B0.57230.26040.86320.113*
H9C0.45560.31220.75920.113*
C100.1496 (11)0.2216 (3)0.6200 (5)0.0843 (15)
H10A0.10520.27100.60320.126*
H10B0.00170.19250.60450.126*
H10C0.26290.20620.57020.126*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.088 (2)0.0629 (17)0.0675 (19)0.0089 (16)0.0494 (17)0.0030 (14)
C10.049 (2)0.0536 (18)0.0456 (18)0.0051 (15)0.0187 (14)0.0018 (15)
C20.049 (2)0.057 (2)0.0417 (16)0.0015 (15)0.0110 (14)0.0078 (13)
Br10.0641 (3)0.0808 (3)0.0603 (2)0.0180 (2)0.02230 (16)0.0113 (2)
C30.056 (3)0.0431 (19)0.049 (2)0.0021 (14)0.0119 (16)0.0012 (14)
C70.116 (4)0.048 (2)0.081 (3)0.010 (2)0.031 (3)0.003 (2)
C40.048 (2)0.056 (2)0.0438 (17)0.0028 (15)0.0138 (14)0.0003 (15)
O20.076 (2)0.0716 (19)0.077 (2)0.0032 (16)0.0386 (18)0.0242 (16)
C50.046 (2)0.0515 (19)0.0420 (16)0.0006 (14)0.0140 (13)0.0011 (14)
Br20.0760 (3)0.0755 (3)0.0633 (2)0.0104 (2)0.04223 (19)0.0018 (2)
C60.050 (2)0.055 (2)0.0427 (18)0.0050 (14)0.0169 (14)0.0052 (14)
C80.066 (3)0.064 (2)0.060 (2)0.0155 (18)0.0317 (18)0.0169 (18)
C90.090 (3)0.051 (2)0.081 (3)0.008 (2)0.008 (2)0.004 (2)
C100.068 (3)0.097 (4)0.084 (3)0.002 (3)0.005 (2)0.035 (3)
Geometric parameters (Å, º) top
O1—C11.218 (5)C5—C61.338 (5)
C1—C21.485 (5)C5—Br21.890 (4)
C1—C61.496 (6)C6—C81.519 (6)
C2—C31.332 (6)C8—C101.510 (6)
C2—Br11.893 (4)C8—C91.540 (7)
C3—C41.494 (6)C8—H80.9800
C3—C71.502 (6)C9—H9A0.9600
C7—H7A0.9600C9—H9B0.9600
C7—H7B0.9600C9—H9C0.9600
C7—H7C0.9600C10—H10A0.9600
C4—O21.208 (5)C10—H10B0.9600
C4—C51.485 (5)C10—H10C0.9600
O1—C1—C2120.9 (4)C5—C6—C1117.1 (3)
O1—C1—C6120.6 (3)C5—C6—C8125.5 (4)
C2—C1—C6118.5 (3)C1—C6—C8117.4 (3)
C3—C2—C1124.0 (3)C10—C8—C6112.6 (4)
C3—C2—Br1122.1 (3)C10—C8—C9111.0 (4)
C1—C2—Br1113.9 (3)C6—C8—C9111.8 (4)
C2—C3—C4117.7 (3)C10—C8—H8107.0
C2—C3—C7125.2 (4)C6—C8—H8107.0
C4—C3—C7117.1 (4)C9—C8—H8107.0
C3—C7—H7A109.5C8—C9—H9A109.5
C3—C7—H7B109.5C8—C9—H9B109.5
H7A—C7—H7B109.5H9A—C9—H9B109.5
C3—C7—H7C109.5C8—C9—H9C109.5
H7A—C7—H7C109.5H9A—C9—H9C109.5
H7B—C7—H7C109.5H9B—C9—H9C109.5
O2—C4—C5121.7 (4)C8—C10—H10A109.5
O2—C4—C3120.1 (4)C8—C10—H10B109.5
C5—C4—C3118.2 (3)H10A—C10—H10B109.5
C6—C5—C4124.2 (3)C8—C10—H10C109.5
C6—C5—Br2122.3 (3)H10A—C10—H10C109.5
C4—C5—Br2113.4 (2)H10B—C10—H10C109.5
O1—C1—C2—C3177.8 (4)O2—C4—C5—Br23.6 (5)
C6—C1—C2—C30.5 (5)C3—C4—C5—Br2176.9 (3)
O1—C1—C2—Br12.1 (5)C4—C5—C6—C15.7 (6)
C6—C1—C2—Br1179.5 (3)Br2—C5—C6—C1175.6 (3)
C1—C2—C3—C41.0 (6)C4—C5—C6—C8173.8 (4)
Br1—C2—C3—C4179.0 (3)Br2—C5—C6—C84.9 (6)
C1—C2—C3—C7180.0 (5)O1—C1—C6—C5174.6 (4)
Br1—C2—C3—C70.0 (6)C2—C1—C6—C53.8 (5)
C2—C3—C4—O2178.8 (4)O1—C1—C6—C85.9 (6)
C7—C3—C4—O22.1 (6)C2—C1—C6—C8175.7 (4)
C2—C3—C4—C50.6 (5)C5—C6—C8—C10119.6 (5)
C7—C3—C4—C5178.5 (4)C1—C6—C8—C1059.9 (5)
O2—C4—C5—C6175.2 (4)C5—C6—C8—C9114.6 (5)
C3—C4—C5—C64.2 (6)C1—C6—C8—C965.9 (5)
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

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