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The title compound, C7H6BrClO, is a starting material for the synthesis of hydroxy­lated metabolites of polychlorinated biphenyls (PCBs). The title compound does not display any unusual bond distances and angles. The meth­oxy group is rotated slightly out of the plane of the benzene ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807013372/wn2130sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807013372/wn2130Isup2.hkl
Contains datablock I

CCDC reference: 647464

Key indicators

  • Single-crystal X-ray study
  • T = 90 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.019
  • wR factor = 0.041
  • Data-to-parameter ratio = 18.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. O1 .. 3.24 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO–SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1994); software used to prepare material for publication: SHELXL97 and local procedures.

4-Bromo-2-chloro-1-methoxy-benzene top
Crystal data top
C7H6BrClOF(000) = 864
Mr = 221.47Dx = 1.936 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2030 reflections
a = 10.7164 (1) Åθ = 1.0–27.5°
b = 8.1340 (2) ŵ = 5.68 mm1
c = 17.4336 (4) ÅT = 90 K
V = 1519.64 (5) Å3Block, colourless
Z = 80.30 × 0.28 × 0.24 mm
Data collection top
Nonius KappaCCD
diffractometer
1747 independent reflections
Radiation source: fine-focus sealed tube1416 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
Detector resolution: 18 pixels mm-1θmax = 27.5°, θmin = 2.3°
ω scansh = 1313
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
k = 1010
Tmin = 0.191, Tmax = 0.256l = 2222
22065 measured reflections
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)] = 0.019H-atom parameters constrained
wR(F2) = 0.041 w = 1/[σ2(Fo2)]
S = 0.96(Δ/σ)max = 0.001
1747 reflectionsΔρmax = 0.39 e Å3
93 parametersΔρmin = 0.34 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00194 (15)
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.

H atoms were found in difference Fourier maps and subsequently placed in idealized positions with constrained C?H distances of 0.98 Å (CHMe) and 0.95 Å (CAr). Uiso(H) values were set to either 1.5Ueq of the attached C atom (CMe) or 1.2Ueq (CAr).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.427177 (16)0.77107 (2)0.102764 (9)0.01450 (7)
Cl10.56457 (4)0.78873 (5)0.40745 (2)0.01559 (11)
O10.34965 (10)0.58973 (13)0.43500 (6)0.0116 (3)
C10.36030 (16)0.62266 (19)0.35903 (9)0.0093 (4)
C20.46178 (16)0.72003 (19)0.33706 (10)0.0105 (4)
C30.48197 (15)0.76374 (19)0.26217 (10)0.0107 (4)
H30.55140.83030.24870.013*
C40.39950 (15)0.7093 (2)0.20626 (10)0.0102 (4)
C50.29784 (15)0.6128 (2)0.22602 (9)0.0112 (4)
H50.24160.57610.18760.013*
C60.27854 (15)0.5700 (2)0.30202 (10)0.0109 (4)
H60.20870.50400.31540.013*
C70.24991 (16)0.4831 (2)0.45805 (11)0.0170 (4)
H7A0.17000.53030.44170.026*
H7B0.25050.47130.51400.026*
H7C0.26100.37500.43420.026*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.01762 (12)0.01710 (12)0.00879 (11)0.00200 (7)0.00038 (8)0.00206 (7)
Cl10.0148 (3)0.0204 (3)0.0116 (2)0.00573 (18)0.00325 (18)0.00149 (18)
O10.0150 (7)0.0119 (6)0.0080 (6)0.0036 (5)0.0026 (5)0.0002 (5)
C10.0122 (10)0.0062 (9)0.0095 (10)0.0039 (7)0.0030 (7)0.0004 (7)
C20.0104 (9)0.0090 (9)0.0120 (9)0.0018 (7)0.0038 (7)0.0025 (7)
C30.0087 (9)0.0090 (9)0.0144 (10)0.0002 (7)0.0019 (8)0.0005 (7)
C40.0140 (9)0.0094 (9)0.0071 (9)0.0044 (7)0.0000 (7)0.0002 (7)
C50.0114 (9)0.0113 (9)0.0109 (10)0.0020 (7)0.0034 (7)0.0027 (7)
C60.0093 (10)0.0094 (9)0.0140 (10)0.0003 (7)0.0011 (8)0.0008 (8)
C70.0183 (11)0.0179 (11)0.0149 (11)0.0069 (8)0.0033 (8)0.0027 (8)
Geometric parameters (Å, º) top
Br1—C41.8964 (17)C3—H30.9500
Cl1—C21.7411 (17)C4—C51.386 (2)
O1—C11.3560 (18)C5—C61.385 (2)
O1—C71.4337 (18)C5—H50.9500
C1—C61.392 (2)C6—H60.9500
C1—C21.399 (2)C7—H7A0.9800
C2—C31.370 (2)C7—H7B0.9800
C3—C41.388 (2)C7—H7C0.9800
C1—O1—C7117.13 (13)C6—C5—C4119.81 (16)
O1—C1—C6125.70 (15)C6—C5—H5120.1
O1—C1—C2116.40 (14)C4—C5—H5120.1
C6—C1—C2117.89 (15)C5—C6—C1120.77 (16)
C3—C2—C1122.04 (16)C5—C6—H6119.6
C3—C2—Cl1119.23 (13)C1—C6—H6119.6
C1—C2—Cl1118.73 (13)O1—C7—H7A109.5
C2—C3—C4119.05 (16)O1—C7—H7B109.5
C2—C3—H3120.5H7A—C7—H7B109.5
C4—C3—H3120.5O1—C7—H7C109.5
C5—C4—C3120.43 (16)H7A—C7—H7C109.5
C5—C4—Br1120.62 (13)H7B—C7—H7C109.5
C3—C4—Br1118.94 (13)
C7—O1—C1—C64.1 (2)C2—C3—C4—C50.3 (2)
C7—O1—C1—C2176.87 (14)C2—C3—C4—Br1179.64 (12)
O1—C1—C2—C3179.15 (15)C3—C4—C5—C60.2 (2)
C6—C1—C2—C30.0 (3)Br1—C4—C5—C6179.47 (12)
O1—C1—C2—Cl10.3 (2)C4—C5—C6—C10.1 (2)
C6—C1—C2—Cl1179.47 (12)O1—C1—C6—C5179.22 (15)
C1—C2—C3—C40.2 (3)C2—C1—C6—C50.2 (2)
Cl1—C2—C3—C4179.73 (12)
 

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