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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
CCDC reference: 647464
Key indicators
- Single-crystal X-ray study
- T = 90 K
- Mean (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
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
C7H6BrClO | F(000) = 864 |
Mr = 221.47 | Dx = 1.936 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 2030 reflections |
a = 10.7164 (1) Å | θ = 1.0–27.5° |
b = 8.1340 (2) Å | µ = 5.68 mm−1 |
c = 17.4336 (4) Å | T = 90 K |
V = 1519.64 (5) Å3 | Block, colourless |
Z = 8 | 0.30 × 0.28 × 0.24 mm |
Data collection top
Nonius KappaCCD diffractometer | 1747 independent reflections |
Radiation source: fine-focus sealed tube | 1416 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
Detector resolution: 18 pixels mm-1 | θmax = 27.5°, θmin = 2.3° |
ω scans | h = −13→13 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | k = −10→10 |
Tmin = 0.191, Tmax = 0.256 | l = −22→22 |
22065 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)] = 0.019 | H-atom parameters constrained |
wR(F2) = 0.041 | w = 1/[σ2(Fo2)] |
S = 0.96 | (Δ/σ)max = 0.001 |
1747 reflections | Δρmax = 0.39 e Å−3 |
93 parameters | Δρmin = −0.34 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: 0.00194 (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 | x | y | z | Uiso*/Ueq | |
Br1 | 0.427177 (16) | 0.77107 (2) | 0.102764 (9) | 0.01450 (7) | |
Cl1 | 0.56457 (4) | 0.78873 (5) | 0.40745 (2) | 0.01559 (11) | |
O1 | 0.34965 (10) | 0.58973 (13) | 0.43500 (6) | 0.0116 (3) | |
C1 | 0.36030 (16) | 0.62266 (19) | 0.35903 (9) | 0.0093 (4) | |
C2 | 0.46178 (16) | 0.72003 (19) | 0.33706 (10) | 0.0105 (4) | |
C3 | 0.48197 (15) | 0.76374 (19) | 0.26217 (10) | 0.0107 (4) | |
H3 | 0.5514 | 0.8303 | 0.2487 | 0.013* | |
C4 | 0.39950 (15) | 0.7093 (2) | 0.20626 (10) | 0.0102 (4) | |
C5 | 0.29784 (15) | 0.6128 (2) | 0.22602 (9) | 0.0112 (4) | |
H5 | 0.2416 | 0.5761 | 0.1876 | 0.013* | |
C6 | 0.27854 (15) | 0.5700 (2) | 0.30202 (10) | 0.0109 (4) | |
H6 | 0.2087 | 0.5040 | 0.3154 | 0.013* | |
C7 | 0.24991 (16) | 0.4831 (2) | 0.45805 (11) | 0.0170 (4) | |
H7A | 0.1700 | 0.5303 | 0.4417 | 0.026* | |
H7B | 0.2505 | 0.4713 | 0.5140 | 0.026* | |
H7C | 0.2610 | 0.3750 | 0.4342 | 0.026* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.01762 (12) | 0.01710 (12) | 0.00879 (11) | −0.00200 (7) | 0.00038 (8) | 0.00206 (7) |
Cl1 | 0.0148 (3) | 0.0204 (3) | 0.0116 (2) | −0.00573 (18) | −0.00325 (18) | −0.00149 (18) |
O1 | 0.0150 (7) | 0.0119 (6) | 0.0080 (6) | −0.0036 (5) | 0.0026 (5) | 0.0002 (5) |
C1 | 0.0122 (10) | 0.0062 (9) | 0.0095 (10) | 0.0039 (7) | 0.0030 (7) | −0.0004 (7) |
C2 | 0.0104 (9) | 0.0090 (9) | 0.0120 (9) | 0.0018 (7) | −0.0038 (7) | −0.0025 (7) |
C3 | 0.0087 (9) | 0.0090 (9) | 0.0144 (10) | −0.0002 (7) | 0.0019 (8) | 0.0005 (7) |
C4 | 0.0140 (9) | 0.0094 (9) | 0.0071 (9) | 0.0044 (7) | 0.0000 (7) | 0.0002 (7) |
C5 | 0.0114 (9) | 0.0113 (9) | 0.0109 (10) | 0.0020 (7) | −0.0034 (7) | −0.0027 (7) |
C6 | 0.0093 (10) | 0.0094 (9) | 0.0140 (10) | −0.0003 (7) | 0.0011 (8) | −0.0008 (8) |
C7 | 0.0183 (11) | 0.0179 (11) | 0.0149 (11) | −0.0069 (8) | 0.0033 (8) | 0.0027 (8) |
Geometric parameters (Å, º) top
Br1—C4 | 1.8964 (17) | C3—H3 | 0.9500 |
Cl1—C2 | 1.7411 (17) | C4—C5 | 1.386 (2) |
O1—C1 | 1.3560 (18) | C5—C6 | 1.385 (2) |
O1—C7 | 1.4337 (18) | C5—H5 | 0.9500 |
C1—C6 | 1.392 (2) | C6—H6 | 0.9500 |
C1—C2 | 1.399 (2) | C7—H7A | 0.9800 |
C2—C3 | 1.370 (2) | C7—H7B | 0.9800 |
C3—C4 | 1.388 (2) | C7—H7C | 0.9800 |
| | | |
C1—O1—C7 | 117.13 (13) | C6—C5—C4 | 119.81 (16) |
O1—C1—C6 | 125.70 (15) | C6—C5—H5 | 120.1 |
O1—C1—C2 | 116.40 (14) | C4—C5—H5 | 120.1 |
C6—C1—C2 | 117.89 (15) | C5—C6—C1 | 120.77 (16) |
C3—C2—C1 | 122.04 (16) | C5—C6—H6 | 119.6 |
C3—C2—Cl1 | 119.23 (13) | C1—C6—H6 | 119.6 |
C1—C2—Cl1 | 118.73 (13) | O1—C7—H7A | 109.5 |
C2—C3—C4 | 119.05 (16) | O1—C7—H7B | 109.5 |
C2—C3—H3 | 120.5 | H7A—C7—H7B | 109.5 |
C4—C3—H3 | 120.5 | O1—C7—H7C | 109.5 |
C5—C4—C3 | 120.43 (16) | H7A—C7—H7C | 109.5 |
C5—C4—Br1 | 120.62 (13) | H7B—C7—H7C | 109.5 |
C3—C4—Br1 | 118.94 (13) | | |
| | | |
C7—O1—C1—C6 | 4.1 (2) | C2—C3—C4—C5 | 0.3 (2) |
C7—O1—C1—C2 | −176.87 (14) | C2—C3—C4—Br1 | 179.64 (12) |
O1—C1—C2—C3 | −179.15 (15) | C3—C4—C5—C6 | −0.2 (2) |
C6—C1—C2—C3 | 0.0 (3) | Br1—C4—C5—C6 | −179.47 (12) |
O1—C1—C2—Cl1 | 0.3 (2) | C4—C5—C6—C1 | −0.1 (2) |
C6—C1—C2—Cl1 | 179.47 (12) | O1—C1—C6—C5 | 179.22 (15) |
C1—C2—C3—C4 | −0.2 (3) | C2—C1—C6—C5 | 0.2 (2) |
Cl1—C2—C3—C4 | −179.73 (12) | | |
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