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
CCDC reference: 1433845
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean
(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
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
C14H10Br2O4 | Z = 2 |
Mr = 402.04 | F(000) = 392 |
Triclinic, P1 | Dx = 1.968 Mg m−3 |
a = 7.0909 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.2120 (8) Å | Cell parameters from 3169 reflections |
c = 10.7056 (10) Å | θ = 3.0–26.5° |
α = 90.989 (3)° | µ = 5.98 mm−1 |
β = 97.098 (3)° | T = 173 K |
γ = 101.909 (3)° | Fragment, brown |
V = 678.35 (10) Å3 | 0.10 × 0.07 × 0.06 mm |
Data collection top
Bruker APEXII CCD diffractometer | 2180 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.036 |
Absorption correction: multi-scan (AXScale; Bruker, 2010) | θmax = 26.6°, θmin = 1.9° |
Tmin = 0.561, Tmax = 0.745 | h = −8→8 |
7453 measured reflections | k = −11→11 |
2714 independent reflections | l = −13→13 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.148 | H-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 parameters | Δρmax = 0.67 e Å−3 |
0 restraints | Δρmin = −1.06 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Br1 | 0.28348 (7) | 0.59976 (6) | 1.11818 (5) | 0.0442 (2) | |
Br2 | 0.25434 (6) | 1.33646 (5) | 0.34039 (4) | 0.0308 (2) | |
O1 | −0.0292 (5) | 0.7668 (4) | 1.0260 (3) | 0.0365 (8) | |
O2 | 0.5998 (4) | 0.9672 (4) | 0.8081 (3) | 0.0282 (7) | |
O3 | 0.2720 (4) | 0.8360 (3) | 0.5689 (3) | 0.0246 (6) | |
O4 | 0.2214 (4) | 1.4265 (3) | 0.6021 (3) | 0.0272 (7) | |
C1 | 0.2910 (6) | 0.7438 (5) | 0.9966 (4) | 0.0258 (9) | |
C2 | 0.1101 (6) | 0.8048 (5) | 0.9676 (4) | 0.0239 (9) | |
C3 | 0.1079 (6) | 0.9086 (5) | 0.8659 (4) | 0.0240 (9) | |
H3A | −0.0054 | 0.9476 | 0.8449 | 0.029* | |
C4 | 0.2593 (6) | 0.9515 (4) | 0.8004 (4) | 0.0189 (8) | |
C5 | 0.4475 (6) | 0.9059 (5) | 0.8446 (4) | 0.0223 (9) | |
C6 | 0.4464 (6) | 0.7913 (5) | 0.9381 (4) | 0.0243 (9) | |
H6A | 0.5583 | 0.7501 | 0.9572 | 0.029* | |
C7 | 0.2536 (5) | 1.0448 (5) | 0.6908 (4) | 0.0215 (9) | |
C8 | 0.2612 (5) | 0.9822 (4) | 0.5715 (4) | 0.0196 (8) | |
C9 | 0.2575 (5) | 1.0693 (4) | 0.4676 (4) | 0.0196 (8) | |
H9A | 0.2624 | 1.0282 | 0.3864 | 0.024* | |
C10 | 0.2465 (5) | 1.2161 (5) | 0.4825 (4) | 0.0200 (8) | |
C11 | 0.2352 (5) | 1.2807 (4) | 0.5986 (4) | 0.0193 (8) | |
C12 | 0.2373 (5) | 1.1929 (5) | 0.7029 (4) | 0.0207 (8) | |
H12A | 0.2275 | 1.2340 | 0.7833 | 0.025* | |
C13 | 0.2659 (6) | 0.7645 (5) | 0.4477 (4) | 0.0241 (9) | |
H13A | 0.2659 | 0.6590 | 0.4580 | 0.036* | |
H13B | 0.3801 | 0.8112 | 0.4087 | 0.036* | |
H13C | 0.1476 | 0.7745 | 0.3938 | 0.036* | |
C14 | 0.2129 (7) | 1.4946 (5) | 0.7220 (5) | 0.0305 (10) | |
H14A | 0.1988 | 1.5974 | 0.7109 | 0.046* | |
H14B | 0.3327 | 1.4938 | 0.7781 | 0.046* | |
H14C | 0.1013 | 1.4394 | 0.7590 | 0.046* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0440 (3) | 0.0453 (4) | 0.0449 (4) | 0.0096 (2) | 0.0080 (2) | 0.0305 (3) |
Br2 | 0.0436 (3) | 0.0247 (3) | 0.0258 (3) | 0.0094 (2) | 0.0065 (2) | 0.01177 (19) |
O1 | 0.0362 (17) | 0.037 (2) | 0.041 (2) | 0.0078 (14) | 0.0193 (15) | 0.0106 (15) |
O2 | 0.0248 (14) | 0.0329 (18) | 0.0288 (18) | 0.0059 (12) | 0.0101 (12) | 0.0073 (13) |
O3 | 0.0345 (16) | 0.0171 (15) | 0.0247 (17) | 0.0089 (12) | 0.0075 (12) | 0.0024 (12) |
O4 | 0.0369 (16) | 0.0190 (16) | 0.0287 (18) | 0.0109 (12) | 0.0071 (13) | 0.0038 (13) |
C1 | 0.031 (2) | 0.020 (2) | 0.025 (2) | 0.0029 (17) | 0.0031 (17) | 0.0069 (18) |
C2 | 0.027 (2) | 0.023 (2) | 0.022 (2) | 0.0014 (16) | 0.0082 (16) | 0.0036 (17) |
C3 | 0.0241 (19) | 0.019 (2) | 0.029 (3) | 0.0056 (16) | 0.0047 (17) | 0.0031 (17) |
C4 | 0.0259 (19) | 0.016 (2) | 0.016 (2) | 0.0052 (15) | 0.0046 (15) | 0.0002 (15) |
C5 | 0.026 (2) | 0.021 (2) | 0.020 (2) | 0.0059 (16) | 0.0037 (16) | −0.0010 (16) |
C6 | 0.028 (2) | 0.026 (2) | 0.019 (2) | 0.0078 (17) | 0.0007 (16) | 0.0027 (17) |
C7 | 0.0158 (17) | 0.019 (2) | 0.030 (2) | 0.0029 (14) | 0.0052 (15) | 0.0037 (17) |
C8 | 0.0177 (17) | 0.015 (2) | 0.026 (2) | 0.0034 (14) | 0.0042 (15) | 0.0040 (16) |
C9 | 0.0176 (17) | 0.019 (2) | 0.023 (2) | 0.0038 (14) | 0.0047 (15) | 0.0035 (16) |
C10 | 0.0157 (17) | 0.025 (2) | 0.019 (2) | 0.0036 (15) | 0.0024 (14) | 0.0079 (17) |
C11 | 0.0169 (17) | 0.0135 (19) | 0.028 (2) | 0.0048 (14) | 0.0035 (15) | 0.0052 (16) |
C12 | 0.0210 (18) | 0.016 (2) | 0.025 (2) | 0.0017 (14) | 0.0068 (15) | 0.0011 (16) |
C13 | 0.026 (2) | 0.019 (2) | 0.027 (2) | 0.0031 (16) | 0.0047 (16) | −0.0037 (17) |
C14 | 0.035 (2) | 0.020 (2) | 0.039 (3) | 0.0101 (18) | 0.0077 (19) | −0.003 (2) |
Geometric parameters (Å, º) top
Br1—C1 | 1.872 (5) | C6—H6A | 0.9500 |
Br2—C10 | 1.897 (4) | C7—C12 | 1.398 (6) |
O1—C2 | 1.227 (5) | C7—C8 | 1.404 (6) |
O2—C5 | 1.224 (5) | C8—C9 | 1.384 (6) |
O3—C8 | 1.365 (5) | C9—C10 | 1.378 (6) |
O3—C13 | 1.437 (5) | C9—H9A | 0.9500 |
O4—C11 | 1.367 (5) | C10—C11 | 1.388 (6) |
O4—C14 | 1.433 (6) | C11—C12 | 1.390 (6) |
C1—C6 | 1.334 (6) | C12—H12A | 0.9500 |
C1—C2 | 1.504 (6) | C13—H13A | 0.9800 |
C2—C3 | 1.462 (6) | C13—H13B | 0.9800 |
C3—C4 | 1.349 (6) | C13—H13C | 0.9800 |
C3—H3A | 0.9500 | C14—H14A | 0.9800 |
C4—C7 | 1.468 (6) | C14—H14B | 0.9800 |
C4—C5 | 1.504 (6) | C14—H14C | 0.9800 |
C5—C6 | 1.467 (6) | | |
| | | |
C8—O3—C13 | 117.3 (3) | C9—C8—C7 | 119.4 (4) |
C11—O4—C14 | 117.8 (3) | C10—C9—C8 | 119.7 (4) |
C6—C1—C2 | 121.0 (4) | C10—C9—H9A | 120.2 |
C6—C1—Br1 | 122.8 (4) | C8—C9—H9A | 120.2 |
C2—C1—Br1 | 116.2 (3) | C9—C10—C11 | 122.4 (4) |
O1—C2—C3 | 122.1 (4) | C9—C10—Br2 | 119.1 (3) |
O1—C2—C1 | 121.0 (4) | C11—C10—Br2 | 118.5 (3) |
C3—C2—C1 | 116.8 (4) | O4—C11—C10 | 117.4 (4) |
C4—C3—C2 | 123.1 (4) | O4—C11—C12 | 124.6 (4) |
C4—C3—H3A | 118.5 | C10—C11—C12 | 118.0 (4) |
C2—C3—H3A | 118.5 | C11—C12—C7 | 120.7 (4) |
C3—C4—C7 | 123.8 (4) | C11—C12—H12A | 119.7 |
C3—C4—C5 | 118.4 (4) | C7—C12—H12A | 119.7 |
C7—C4—C5 | 117.8 (3) | O3—C13—H13A | 109.5 |
O2—C5—C6 | 120.5 (4) | O3—C13—H13B | 109.5 |
O2—C5—C4 | 121.1 (4) | H13A—C13—H13B | 109.5 |
C6—C5—C4 | 118.3 (4) | O3—C13—H13C | 109.5 |
C1—C6—C5 | 121.2 (4) | H13A—C13—H13C | 109.5 |
C1—C6—H6A | 119.4 | H13B—C13—H13C | 109.5 |
C5—C6—H6A | 119.4 | O4—C14—H14A | 109.5 |
C12—C7—C8 | 119.8 (4) | O4—C14—H14B | 109.5 |
C12—C7—C4 | 121.3 (4) | H14A—C14—H14B | 109.5 |
C8—C7—C4 | 118.9 (3) | O4—C14—H14C | 109.5 |
O3—C8—C9 | 125.2 (4) | H14A—C14—H14C | 109.5 |
O3—C8—C7 | 115.4 (4) | H14B—C14—H14C | 109.5 |
Hydrogen-bond geometry (Å, º) topCg1 and Cg2 are the centroids of the C1–C6 and C7–C12
rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9A···O2i | 0.95 | 2.40 | 3.270 (5) | 151 |
C12—H12A···O1ii | 0.95 | 2.62 | 3.461 (5) | 148 |
C13—H13A···O4iii | 0.98 | 2.65 | 3.525 (5) | 149 |
C13—H13B···Cg2i | 0.98 | 2.57 | 3.443 (5) | 148 |
C14—H14A···Cg1iv | 0.98 | 3.00 | 3.695 (5) | 129 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y+2, −z+2; (iii) x, y−1, z; (iv) x, y+1, z. |