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In the crystal, mol­ecules pack in a centrosymmetric fashion and inter­act via a mixture of weak π–π stacking inter­actions, weak C—H...O hydrogen bonding, and Br...Br halogen bonding. This induces a geometry quite different than that predicted by theory.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015020472/hb7514sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989015020472/hb7514Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015020472/hb7514Isup3.cml
Supplementary material

CCDC reference: 1433845

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.043
  • wR factor = 0.148
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.968 Note PLAT480_ALERT_4_C Long H...A H-Bond Reported H12A .. O1 .. 2.62 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H13A .. O4 .. 2.65 Ang. PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 79 Report PLAT975_ALERT_2_C Check Calcd Residual Density 1.05A From O3 0.65 eA-3
Alert level G PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large. 0.11 Report PLAT154_ALERT_1_G The su's on the Cell Angles are Equal .......... 0.00300 Degree PLAT335_ALERT_2_G Check Large C6 Ring C-C Range C1 -C6 0.17 Ang. PLAT434_ALERT_2_G Short Inter HL..HL Contact Br1 .. Br2 .. 3.42 Ang. PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 43 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 5 ALERT level C = Check. Ensure it is not caused by an omission or oversight 5 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

4,4'-Dibromo-2',5'-dimethoxy-[1,1'-biphenyl]-2,5-dione top
Crystal data top
C14H10Br2O4Z = 2
Mr = 402.04F(000) = 392
Triclinic, P1Dx = 1.968 Mg m3
a = 7.0909 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.2120 (8) ÅCell parameters from 3169 reflections
c = 10.7056 (10) Åθ = 3.0–26.5°
α = 90.989 (3)°µ = 5.98 mm1
β = 97.098 (3)°T = 173 K
γ = 101.909 (3)°Fragment, brown
V = 678.35 (10) Å30.10 × 0.07 × 0.06 mm
Data collection top
Bruker APEXII CCD
diffractometer
2180 reflections with I > 2σ(I)
φ and ω scansRint = 0.036
Absorption correction: multi-scan
(AXScale; Bruker, 2010)
θmax = 26.6°, θmin = 1.9°
Tmin = 0.561, Tmax = 0.745h = 88
7453 measured reflectionsk = 1111
2714 independent reflectionsl = 1313
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.1053P)2]
where P = (Fo2 + 2Fc2)/3
2714 reflections(Δ/σ)max = 0.001
183 parametersΔρmax = 0.67 e Å3
0 restraintsΔρmin = 1.06 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.28348 (7)0.59976 (6)1.11818 (5)0.0442 (2)
Br20.25434 (6)1.33646 (5)0.34039 (4)0.0308 (2)
O10.0292 (5)0.7668 (4)1.0260 (3)0.0365 (8)
O20.5998 (4)0.9672 (4)0.8081 (3)0.0282 (7)
O30.2720 (4)0.8360 (3)0.5689 (3)0.0246 (6)
O40.2214 (4)1.4265 (3)0.6021 (3)0.0272 (7)
C10.2910 (6)0.7438 (5)0.9966 (4)0.0258 (9)
C20.1101 (6)0.8048 (5)0.9676 (4)0.0239 (9)
C30.1079 (6)0.9086 (5)0.8659 (4)0.0240 (9)
H3A0.00540.94760.84490.029*
C40.2593 (6)0.9515 (4)0.8004 (4)0.0189 (8)
C50.4475 (6)0.9059 (5)0.8446 (4)0.0223 (9)
C60.4464 (6)0.7913 (5)0.9381 (4)0.0243 (9)
H6A0.55830.75010.95720.029*
C70.2536 (5)1.0448 (5)0.6908 (4)0.0215 (9)
C80.2612 (5)0.9822 (4)0.5715 (4)0.0196 (8)
C90.2575 (5)1.0693 (4)0.4676 (4)0.0196 (8)
H9A0.26241.02820.38640.024*
C100.2465 (5)1.2161 (5)0.4825 (4)0.0200 (8)
C110.2352 (5)1.2807 (4)0.5986 (4)0.0193 (8)
C120.2373 (5)1.1929 (5)0.7029 (4)0.0207 (8)
H12A0.22751.23400.78330.025*
C130.2659 (6)0.7645 (5)0.4477 (4)0.0241 (9)
H13A0.26590.65900.45800.036*
H13B0.38010.81120.40870.036*
H13C0.14760.77450.39380.036*
C140.2129 (7)1.4946 (5)0.7220 (5)0.0305 (10)
H14A0.19881.59740.71090.046*
H14B0.33271.49380.77810.046*
H14C0.10131.43940.75900.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0440 (3)0.0453 (4)0.0449 (4)0.0096 (2)0.0080 (2)0.0305 (3)
Br20.0436 (3)0.0247 (3)0.0258 (3)0.0094 (2)0.0065 (2)0.01177 (19)
O10.0362 (17)0.037 (2)0.041 (2)0.0078 (14)0.0193 (15)0.0106 (15)
O20.0248 (14)0.0329 (18)0.0288 (18)0.0059 (12)0.0101 (12)0.0073 (13)
O30.0345 (16)0.0171 (15)0.0247 (17)0.0089 (12)0.0075 (12)0.0024 (12)
O40.0369 (16)0.0190 (16)0.0287 (18)0.0109 (12)0.0071 (13)0.0038 (13)
C10.031 (2)0.020 (2)0.025 (2)0.0029 (17)0.0031 (17)0.0069 (18)
C20.027 (2)0.023 (2)0.022 (2)0.0014 (16)0.0082 (16)0.0036 (17)
C30.0241 (19)0.019 (2)0.029 (3)0.0056 (16)0.0047 (17)0.0031 (17)
C40.0259 (19)0.016 (2)0.016 (2)0.0052 (15)0.0046 (15)0.0002 (15)
C50.026 (2)0.021 (2)0.020 (2)0.0059 (16)0.0037 (16)0.0010 (16)
C60.028 (2)0.026 (2)0.019 (2)0.0078 (17)0.0007 (16)0.0027 (17)
C70.0158 (17)0.019 (2)0.030 (2)0.0029 (14)0.0052 (15)0.0037 (17)
C80.0177 (17)0.015 (2)0.026 (2)0.0034 (14)0.0042 (15)0.0040 (16)
C90.0176 (17)0.019 (2)0.023 (2)0.0038 (14)0.0047 (15)0.0035 (16)
C100.0157 (17)0.025 (2)0.019 (2)0.0036 (15)0.0024 (14)0.0079 (17)
C110.0169 (17)0.0135 (19)0.028 (2)0.0048 (14)0.0035 (15)0.0052 (16)
C120.0210 (18)0.016 (2)0.025 (2)0.0017 (14)0.0068 (15)0.0011 (16)
C130.026 (2)0.019 (2)0.027 (2)0.0031 (16)0.0047 (16)0.0037 (17)
C140.035 (2)0.020 (2)0.039 (3)0.0101 (18)0.0077 (19)0.003 (2)
Geometric parameters (Å, º) top
Br1—C11.872 (5)C6—H6A0.9500
Br2—C101.897 (4)C7—C121.398 (6)
O1—C21.227 (5)C7—C81.404 (6)
O2—C51.224 (5)C8—C91.384 (6)
O3—C81.365 (5)C9—C101.378 (6)
O3—C131.437 (5)C9—H9A0.9500
O4—C111.367 (5)C10—C111.388 (6)
O4—C141.433 (6)C11—C121.390 (6)
C1—C61.334 (6)C12—H12A0.9500
C1—C21.504 (6)C13—H13A0.9800
C2—C31.462 (6)C13—H13B0.9800
C3—C41.349 (6)C13—H13C0.9800
C3—H3A0.9500C14—H14A0.9800
C4—C71.468 (6)C14—H14B0.9800
C4—C51.504 (6)C14—H14C0.9800
C5—C61.467 (6)
C8—O3—C13117.3 (3)C9—C8—C7119.4 (4)
C11—O4—C14117.8 (3)C10—C9—C8119.7 (4)
C6—C1—C2121.0 (4)C10—C9—H9A120.2
C6—C1—Br1122.8 (4)C8—C9—H9A120.2
C2—C1—Br1116.2 (3)C9—C10—C11122.4 (4)
O1—C2—C3122.1 (4)C9—C10—Br2119.1 (3)
O1—C2—C1121.0 (4)C11—C10—Br2118.5 (3)
C3—C2—C1116.8 (4)O4—C11—C10117.4 (4)
C4—C3—C2123.1 (4)O4—C11—C12124.6 (4)
C4—C3—H3A118.5C10—C11—C12118.0 (4)
C2—C3—H3A118.5C11—C12—C7120.7 (4)
C3—C4—C7123.8 (4)C11—C12—H12A119.7
C3—C4—C5118.4 (4)C7—C12—H12A119.7
C7—C4—C5117.8 (3)O3—C13—H13A109.5
O2—C5—C6120.5 (4)O3—C13—H13B109.5
O2—C5—C4121.1 (4)H13A—C13—H13B109.5
C6—C5—C4118.3 (4)O3—C13—H13C109.5
C1—C6—C5121.2 (4)H13A—C13—H13C109.5
C1—C6—H6A119.4H13B—C13—H13C109.5
C5—C6—H6A119.4O4—C14—H14A109.5
C12—C7—C8119.8 (4)O4—C14—H14B109.5
C12—C7—C4121.3 (4)H14A—C14—H14B109.5
C8—C7—C4118.9 (3)O4—C14—H14C109.5
O3—C8—C9125.2 (4)H14A—C14—H14C109.5
O3—C8—C7115.4 (4)H14B—C14—H14C109.5
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C9—H9A···O2i0.952.403.270 (5)151
C12—H12A···O1ii0.952.623.461 (5)148
C13—H13A···O4iii0.982.653.525 (5)149
C13—H13B···Cg2i0.982.573.443 (5)148
C14—H14A···Cg1iv0.983.003.695 (5)129
Symmetry codes: (i) x+1, y+2, z+1; (ii) x, y+2, z+2; (iii) x, y1, z; (iv) x, y+1, z.
 

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