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The title compound, C7H4Br2O, has mirror symmetry perpendicular to the tropone ring, and forms a head-to-head association of two nearly parallel mol­ecules. Intermolecular π–π, halogen–halogen and C—H...O interactions are observed in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805020210/ob6539sup1.cif
Contains datablocks General, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805020210/ob6539Isup2.hkl
Contains datablock I

CCDC reference: 282553

Key indicators

  • Single-crystal X-ray study
  • T = 123 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.019
  • wR factor = 0.047
  • Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. Br1 .. 3.41 Ang. PLAT703_ALERT_1_C Torsion Calc 154.5(4), Rep 154.0(10), Dev.. 1.25 Sigma BR1 -C2 -C1 -BR1 1.555 1.555 1.555 4.555 PLAT733_ALERT_1_C Torsion Calc 154.5(4), Rep 154.0(10) ...... 2.50 su-Rat BR1 -C2 -C1 -BR1 1.555 1.555 1.555 4.555 PLAT734_ALERT_1_C Contact Calc 2.8068(11), Rep 2.8068(5) ...... 2.20 su-Rat BR1 -C1 1.555 1.555 PLAT734_ALERT_1_C Contact Calc 2.8068(11), Rep 2.8068(5) ...... 2.20 su-Rat C1 -BR1 1.555 4.555 PLAT734_ALERT_1_C Contact Calc 3.4115(12), Rep 3.4115(3) ...... 4.00 su-Rat BR1 -BR1 1.555 3.557
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 5 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC & Rigaku, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: program( reference)?; software used to prepare material for publication: CrystalStructure.

(I) top
Crystal data top
C7H4Br2OF(000) = 248.00
Mr = 263.92Dx = 2.416 Mg m3
Monoclinic, P121/m1Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybCell parameters from 1084 reflections
a = 4.010 (1) Åθ = 3.3–27.5°
b = 14.829 (5) ŵ = 11.12 mm1
c = 6.111 (2) ÅT = 123 K
β = 93.274 (2)°Platelet, yellow
V = 362.8 (2) Å30.13 × 0.03 × 0.02 mm
Z = 2
Data collection top
Rigaku Saturn
diffractometer
684 reflections with F2 > 2σ(F2)
Detector resolution: 7.31 pixels mm-1Rint = 0.031
ω scansθmax = 27.5°
Absorption correction: multi-scan
(Jacobson, 1998)
h = 55
Tmin = 0.606, Tmax = 0.801k = 1919
4008 measured reflectionsl = 77
859 independent reflections
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.019 w = 1/[σ2(Fo2) + (0.0297P)2 + 0.107P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.047(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.64 e Å3
859 reflectionsΔρmin = 0.42 e Å3
50 parameters
Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using reflections with F2 > 3.0 σ(F2). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.12126 (5)0.063640 (10)0.78602 (3)0.01954 (10)
O10.0639 (6)0.25000.8574 (4)0.0223 (5)
C10.1221 (7)0.25000.7057 (5)0.0145 (6)
C20.2383 (5)0.1645 (1)0.6136 (3)0.0142 (4)
C30.4002 (5)0.1454 (1)0.4314 (3)0.0156 (4)
C40.5244 (5)0.2044 (1)0.2710 (3)0.0167 (4)
H10.43630.08430.40690.019*
H20.61670.17690.15190.020*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0250 (1)0.0126 (1)0.0218 (1)0.00130 (8)0.00841 (9)0.00360 (7)
O10.0293 (12)0.0190 (11)0.0203 (11)0.00000.0150 (9)0.0000
C10.0147 (13)0.014 (1)0.0143 (13)0.00000.0014 (10)0.0000
C20.0129 (9)0.0136 (9)0.0159 (9)0.0034 (7)0.0003 (7)0.0014 (7)
C30.0170 (10)0.0113 (9)0.0187 (10)0.0001 (8)0.0021 (8)0.0015 (8)
C40.0180 (9)0.0198 (11)0.0127 (9)0.0010 (8)0.0044 (7)0.0021 (8)
Geometric parameters (Å, º) top
Br1—C21.903 (2)C3—C41.425 (3)
O1—C11.223 (4)C4—C4i1.352 (3)
C1—C21.474 (3)C3—H10.9300
C1—C2i1.474 (3)C4—H20.9300
C2—C31.350 (3)
Br1···O12.9010 (7)Br1···H1xi3.3020
Br1···C12.8068 (5)Br1···H1xii3.0971
Br1···C32.774 (2)Br1···H2iv3.5252
O1···Br1i2.9010 (7)Br1···H2v3.3550
O1···C1ii3.342 (4)O1···H2iv2.5132
O1···C2ii3.344 (3)O1···H2v3.3616
O1···C22.346 (3)O1···H2vi2.5132
O1···C2iii3.344 (3)O1···H2vii3.3616
O1···C2i2.346 (3)C1···H13.3492
O1···C4iv3.170 (3)C1···H1i3.3492
O1···C4v3.425 (3)C1···H2v3.4532
O1···C4vi3.170 (3)C1···H2vii3.4532
O1···C4vii3.425 (3)C2···H1ii3.5893
C1···Br1i2.8068 (5)C2···H11.9367
C1···O1viii3.342 (4)C2···H23.2842
C1···C32.583 (3)C2···H2v3.5478
C1···C3i2.583 (3)C3···H1xii3.5967
C1···C4ii3.540 (3)C3···H2ii3.5207
C1···C43.256 (4)C3···H22.0149
C1···C4iii3.540 (3)C3···H2i3.2847
C1···C4i3.256 (4)C4···H12.0043
C2···O1viii3.344 (3)C4···H1i3.2649
C2···C2i2.537 (3)C4···H2i1.9487
C2···C3ii3.490 (3)H1···Br1viii3.5040
C2···C3i3.114 (3)H1···Br1xi3.3020
C2···C4ii3.499 (3)H1···Br1xii3.0971
C2···C42.515 (3)H1···C2viii3.5893
C2···C4i3.123 (3)H1···C3xii3.5967
C3···C2viii3.490 (3)H1···C4i3.2649
C3···C2i3.114 (3)H2···Br1ix3.3550
C3···C3i3.103 (3)H2···Br1x3.5252
C3···C4i2.495 (3)H2···O1ix3.3616
C4···O1ix3.425 (3)H2···O1x2.5132
C4···O1x3.170 (3)H2···C1ix3.4532
C4···C1viii3.540 (3)H2···C2ix3.5478
C4···C2viii3.499 (3)H2···C3viii3.5207
C4···C2i3.123 (3)H2···C3i3.2847
C4···C3i2.495 (3)H2···C4i1.9487
Br1···H1ii3.5040Br1···Br1xiii3.4115 (3)
Br1···H12.7188
Br1—C2—C1111.8 (2)C2—C3—C4129.9 (2)
Br1—C2—C3115.9 (2)C3—C4—C4i127.9 (2)
O1—C1—C2120.6 (1)C4—C4i—C3i127.9 (2)
O1—C1—C2i120.6 (1)C2—C3—H1115.0374
C1—C2—C3132.2 (2)H1—C3—C4115.0391
C2i—C1—C2118.8 (2)C3—C4—H2116.0533
C1—C2i—Br1i111.8 (2)H2—C4—C4i116.0481
C1—C2i—C3i132.2 (2)C4—C4i—H2i116.0481
O1—C1—C2—Br19.0 (4)C3—C2—C1—C2i11.8 (5)
O1—C1—C2—C3169.1 (3)Br1—C2—C1—Br1i154 (1)
Br1—C2—C3—C4179.2 (2)C2—C3—C4—C4i4.0 (4)
C1—C2—C3—C42.8 (4)
Symmetry codes: (i) x, y+1/2, z; (ii) x1, y, z; (iii) x1, y+1/2, z; (iv) x1, y, z+1; (v) x, y, z+1; (vi) x1, y+1/2, z+1; (vii) x, y+1/2, z+1; (viii) x+1, y, z; (ix) x, y, z1; (x) x+1, y, z1; (xi) x, y, z+1; (xii) x+1, y, z+1; (xiii) x, y, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H2···O1x0.932.513.170 (3)128
Symmetry code: (x) x+1, y, z1.
 

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