Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807035702/kj2060sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807035702/kj2060Isup2.hkl |
CCDC reference: 663694
Key indicators
- Single-crystal X-ray study
- T = 93 K
- Mean (C-C) = 0.003 Å
- R factor = 0.019
- wR factor = 0.047
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.93 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H22 .. BR2 .. 2.97 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H15 .. BR1 .. 3.03 Ang.
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.929 Tmax scaled 0.524 Tmin scaled 0.496
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The paddle-wheel conformation is also a typical feature of the parent substance tetraphenylcyclone (Barnes et al., 1991; Alvarez-Toledano et al., 1997) and the related compound phencyclone (Ruffani et al., 2006), both involving C—H···π contacts in the crystal packing, similar to the title compound. For related literature, see: Dilthey et al. (1935).
The title compound was synthesized according to the procedure described by Dilthey et al. (1935) from 1,2-bis(4-bromophenyl) ethane-1,2-dione, dibenzyl ketone and finely powdered potassium hydroxide in ethanol. Recrystallization from ethyl acetate yielded 72% dark-violet crystals.
The H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95 Å, and Uiso = 1.2–1.5 Ueq(parent atom).
The molecular geometry is best described by a paddle-wheel fashion, due to steric hindrance of the neighbouring aryl rings. The crystal packing is dominated by intramolecular C—H···π interactions. These intermolecular contacts, where π is an aromatic-ring centroid, with H···π distances ranging from 2.67 to 2.90 Å give rise to the formation of molecular chains extended along the a and b axis. Furthermore, unusual C—H···Br contacts forming a three-dimensional network can be observed (Figure 2).
The paddle-wheel conformation is also a typical feature of the parent substance tetraphenylcyclone (Barnes et al., 1991; Alvarez-Toledano et al., 1997) and the related compound phencyclone (Ruffani et al., 2006), both involving C—H···π contacts in the crystal packing, similar to the title compound. For related literature, see: Dilthey et al. (1935).
Data collection: APEX2 (Bruker, YEAR?); cell refinement: SMART (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Fig. 1. Perspective view of (I), showing 50% probability displacement ellipsoids for the non-H atoms. | |
Fig. 2. Packing diagram of (I), viewed down the b axis, with C—H···Br contacts as broken lines. |
C29H18Br2O | F(000) = 1080 |
Mr = 542.25 | Dx = 1.586 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.0677 (4) Å | Cell parameters from 5575 reflections |
b = 9.6526 (4) Å | θ = 2.5–28.7° |
c = 23.6791 (9) Å | µ = 3.59 mm−1 |
β = 99.193 (2)° | T = 93 K |
V = 2271.57 (16) Å3 | Plate, dark-violet |
Z = 4 | 0.20 × 0.19 × 0.18 mm |
Bruker KappaCCD APEXII area-detector diffractometer | 3999 independent reflections |
Radiation source: fine-focus sealed tube | 3578 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
φ and ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −11→11 |
Tmin = 0.534, Tmax = 0.564 | k = −11→11 |
21955 measured reflections | l = −23→28 |
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)] = 0.019 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.047 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0196P)2 + 1.357P] where P = (Fo2 + 2Fc2)/3 |
3999 reflections | (Δ/σ)max = 0.002 |
289 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
C29H18Br2O | V = 2271.57 (16) Å3 |
Mr = 542.25 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.0677 (4) Å | µ = 3.59 mm−1 |
b = 9.6526 (4) Å | T = 93 K |
c = 23.6791 (9) Å | 0.20 × 0.19 × 0.18 mm |
β = 99.193 (2)° |
Bruker KappaCCD APEXII area-detector diffractometer | 3999 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | 3578 reflections with I > 2σ(I) |
Tmin = 0.534, Tmax = 0.564 | Rint = 0.024 |
21955 measured reflections |
R[F2 > 2σ(F2)] = 0.019 | 0 restraints |
wR(F2) = 0.047 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.34 e Å−3 |
3999 reflections | Δρmin = −0.26 e Å−3 |
289 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 1.11380 (13) | 0.81448 (14) | 0.50405 (5) | 0.0234 (3) | |
Br1 | 0.453140 (18) | 0.255240 (19) | 0.278725 (8) | 0.02000 (6) | |
Br2 | 1.088680 (19) | 0.50624 (2) | 0.125864 (7) | 0.02318 (6) | |
C1 | 1.06412 (18) | 0.74769 (18) | 0.46290 (7) | 0.0171 (4) | |
C2 | 0.92780 (18) | 0.67815 (18) | 0.45385 (7) | 0.0156 (4) | |
C3 | 0.91426 (18) | 0.61459 (18) | 0.40263 (7) | 0.0152 (4) | |
C4 | 1.03677 (18) | 0.64253 (18) | 0.37486 (7) | 0.0147 (4) | |
C5 | 1.12617 (18) | 0.71972 (18) | 0.40982 (7) | 0.0155 (4) | |
C6 | 1.25237 (18) | 0.78587 (18) | 0.39981 (7) | 0.0156 (4) | |
C7 | 1.26415 (19) | 0.84047 (18) | 0.34603 (8) | 0.0173 (4) | |
H7 | 1.1912 | 0.8320 | 0.3154 | 0.021* | |
C8 | 1.38078 (19) | 0.90662 (19) | 0.33701 (8) | 0.0203 (4) | |
H8 | 1.3872 | 0.9434 | 0.3003 | 0.024* | |
C9 | 1.48880 (19) | 0.91968 (19) | 0.38138 (8) | 0.0220 (4) | |
H9 | 1.5690 | 0.9647 | 0.3750 | 0.026* | |
C10 | 1.47859 (19) | 0.86662 (19) | 0.43476 (8) | 0.0217 (4) | |
H10 | 1.5521 | 0.8753 | 0.4651 | 0.026* | |
C11 | 1.36124 (19) | 0.80057 (19) | 0.44427 (8) | 0.0187 (4) | |
H11 | 1.3550 | 0.7652 | 0.4812 | 0.022* | |
C12 | 0.83491 (18) | 0.68419 (19) | 0.49612 (7) | 0.0154 (4) | |
C13 | 0.82388 (18) | 0.80643 (19) | 0.52658 (7) | 0.0178 (4) | |
H13 | 0.8795 | 0.8833 | 0.5213 | 0.021* | |
C14 | 0.73240 (19) | 0.8167 (2) | 0.56443 (8) | 0.0203 (4) | |
H14 | 0.7259 | 0.9002 | 0.5850 | 0.024* | |
C15 | 0.65065 (19) | 0.7056 (2) | 0.57225 (8) | 0.0217 (4) | |
H15 | 0.5871 | 0.7133 | 0.5977 | 0.026* | |
C16 | 0.6614 (2) | 0.5828 (2) | 0.54287 (8) | 0.0220 (4) | |
H16 | 0.6057 | 0.5062 | 0.5484 | 0.026* | |
C17 | 0.75368 (19) | 0.57192 (19) | 0.50535 (7) | 0.0186 (4) | |
H17 | 0.7616 | 0.4872 | 0.4857 | 0.022* | |
C18 | 0.80114 (18) | 0.52985 (18) | 0.37389 (7) | 0.0142 (4) | |
C19 | 0.66960 (18) | 0.58029 (18) | 0.36437 (7) | 0.0162 (4) | |
H19 | 0.6517 | 0.6704 | 0.3774 | 0.019* | |
C20 | 0.56437 (18) | 0.50109 (19) | 0.33620 (8) | 0.0173 (4) | |
H20 | 0.4751 | 0.5363 | 0.3296 | 0.021* | |
C21 | 0.59257 (18) | 0.36977 (18) | 0.31805 (7) | 0.0153 (4) | |
C22 | 0.72124 (19) | 0.31713 (19) | 0.32679 (8) | 0.0217 (4) | |
H22 | 0.7383 | 0.2267 | 0.3138 | 0.026* | |
C23 | 0.82536 (19) | 0.39715 (19) | 0.35460 (8) | 0.0211 (4) | |
H23 | 0.9144 | 0.3614 | 0.3606 | 0.025* | |
C24 | 1.04490 (18) | 0.59994 (18) | 0.31555 (7) | 0.0147 (4) | |
C25 | 0.94423 (18) | 0.63988 (19) | 0.27082 (7) | 0.0173 (4) | |
H25 | 0.8671 | 0.6873 | 0.2793 | 0.021* | |
C26 | 0.95508 (18) | 0.61145 (19) | 0.21434 (8) | 0.0183 (4) | |
H26 | 0.8871 | 0.6404 | 0.1841 | 0.022* | |
C27 | 1.06679 (19) | 0.54023 (18) | 0.20290 (7) | 0.0166 (4) | |
C28 | 1.16667 (18) | 0.49671 (18) | 0.24641 (8) | 0.0171 (4) | |
H28 | 1.2422 | 0.4469 | 0.2377 | 0.021* | |
C29 | 1.15549 (18) | 0.52640 (18) | 0.30265 (8) | 0.0164 (4) | |
H29 | 1.2236 | 0.4965 | 0.3327 | 0.020* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0216 (7) | 0.0311 (8) | 0.0170 (7) | −0.0036 (6) | 0.0015 (6) | −0.0078 (6) |
Br1 | 0.01865 (11) | 0.01994 (11) | 0.02038 (10) | −0.00453 (8) | −0.00005 (7) | −0.00154 (7) |
Br2 | 0.02779 (12) | 0.02861 (11) | 0.01347 (10) | −0.00723 (9) | 0.00428 (8) | −0.00567 (8) |
C1 | 0.0184 (10) | 0.0169 (9) | 0.0155 (9) | 0.0032 (8) | 0.0011 (8) | 0.0006 (8) |
C2 | 0.0164 (10) | 0.0137 (9) | 0.0162 (9) | 0.0014 (8) | 0.0011 (7) | 0.0006 (7) |
C3 | 0.0160 (10) | 0.0143 (9) | 0.0154 (9) | 0.0033 (7) | 0.0022 (7) | 0.0019 (7) |
C4 | 0.0150 (9) | 0.0132 (9) | 0.0155 (9) | 0.0035 (7) | 0.0013 (7) | 0.0008 (7) |
C5 | 0.0153 (9) | 0.0164 (9) | 0.0144 (9) | 0.0035 (7) | 0.0010 (7) | 0.0017 (7) |
C6 | 0.0151 (10) | 0.0145 (9) | 0.0174 (9) | 0.0028 (7) | 0.0029 (7) | −0.0028 (7) |
C7 | 0.0199 (10) | 0.0149 (9) | 0.0169 (9) | 0.0012 (8) | 0.0023 (7) | −0.0028 (7) |
C8 | 0.0268 (11) | 0.0171 (9) | 0.0187 (9) | 0.0013 (8) | 0.0091 (8) | −0.0024 (8) |
C9 | 0.0176 (10) | 0.0192 (10) | 0.0311 (11) | −0.0013 (8) | 0.0096 (8) | −0.0034 (8) |
C10 | 0.0161 (10) | 0.0218 (10) | 0.0261 (10) | 0.0027 (8) | −0.0001 (8) | −0.0042 (8) |
C11 | 0.0198 (10) | 0.0183 (9) | 0.0180 (9) | 0.0021 (8) | 0.0030 (8) | 0.0000 (7) |
C12 | 0.0147 (9) | 0.0197 (9) | 0.0111 (8) | 0.0032 (8) | −0.0006 (7) | 0.0005 (7) |
C13 | 0.0165 (10) | 0.0193 (9) | 0.0168 (9) | −0.0010 (8) | 0.0002 (7) | −0.0007 (7) |
C14 | 0.0212 (10) | 0.0239 (10) | 0.0148 (9) | 0.0049 (8) | 0.0003 (8) | −0.0040 (8) |
C15 | 0.0201 (10) | 0.0320 (11) | 0.0138 (9) | 0.0041 (9) | 0.0052 (8) | 0.0026 (8) |
C16 | 0.0247 (11) | 0.0247 (10) | 0.0167 (9) | −0.0027 (9) | 0.0039 (8) | 0.0053 (8) |
C17 | 0.0249 (11) | 0.0167 (9) | 0.0140 (9) | 0.0025 (8) | 0.0026 (8) | 0.0008 (7) |
C18 | 0.0168 (10) | 0.0149 (9) | 0.0114 (9) | −0.0007 (7) | 0.0033 (7) | 0.0011 (7) |
C19 | 0.0200 (10) | 0.0138 (9) | 0.0155 (9) | 0.0021 (8) | 0.0049 (7) | −0.0012 (7) |
C20 | 0.0142 (9) | 0.0202 (10) | 0.0180 (9) | 0.0024 (8) | 0.0037 (7) | 0.0028 (7) |
C21 | 0.0165 (10) | 0.0165 (9) | 0.0127 (9) | −0.0046 (8) | 0.0013 (7) | 0.0006 (7) |
C22 | 0.0224 (11) | 0.0154 (10) | 0.0267 (10) | 0.0025 (8) | 0.0025 (8) | −0.0055 (8) |
C23 | 0.0139 (10) | 0.0204 (10) | 0.0282 (11) | 0.0042 (8) | 0.0013 (8) | −0.0031 (8) |
C24 | 0.0156 (9) | 0.0133 (9) | 0.0149 (9) | −0.0023 (7) | 0.0018 (7) | −0.0008 (7) |
C25 | 0.0157 (10) | 0.0171 (9) | 0.0192 (9) | 0.0011 (8) | 0.0029 (7) | −0.0004 (7) |
C26 | 0.0168 (10) | 0.0194 (10) | 0.0169 (9) | −0.0025 (8) | −0.0027 (8) | 0.0019 (7) |
C27 | 0.0220 (10) | 0.0147 (9) | 0.0132 (9) | −0.0066 (8) | 0.0036 (7) | −0.0025 (7) |
C28 | 0.0164 (10) | 0.0154 (9) | 0.0205 (10) | −0.0004 (8) | 0.0054 (8) | −0.0012 (7) |
C29 | 0.0160 (10) | 0.0159 (9) | 0.0163 (9) | 0.0001 (8) | −0.0010 (7) | 0.0002 (7) |
O1—C1 | 1.208 (2) | C14—C15 | 1.382 (3) |
Br1—C21 | 1.9084 (17) | C14—H14 | 0.9500 |
Br2—C27 | 1.9006 (17) | C15—C16 | 1.387 (3) |
C1—C2 | 1.512 (3) | C15—H15 | 0.9500 |
C1—C5 | 1.514 (2) | C16—C17 | 1.388 (3) |
C2—C3 | 1.347 (2) | C16—H16 | 0.9500 |
C2—C12 | 1.476 (2) | C17—H17 | 0.9500 |
C3—C18 | 1.477 (2) | C18—C23 | 1.394 (3) |
C3—C4 | 1.512 (2) | C18—C19 | 1.395 (3) |
C4—C5 | 1.346 (3) | C19—C20 | 1.388 (3) |
C4—C24 | 1.478 (2) | C19—H19 | 0.9500 |
C5—C6 | 1.475 (3) | C20—C21 | 1.382 (3) |
C6—C11 | 1.400 (3) | C20—H20 | 0.9500 |
C6—C7 | 1.401 (2) | C21—C22 | 1.376 (3) |
C7—C8 | 1.383 (3) | C22—C23 | 1.381 (3) |
C7—H7 | 0.9500 | C22—H22 | 0.9500 |
C8—C9 | 1.392 (3) | C23—H23 | 0.9500 |
C8—H8 | 0.9500 | C24—C29 | 1.395 (3) |
C9—C10 | 1.383 (3) | C24—C25 | 1.398 (2) |
C9—H9 | 0.9500 | C25—C26 | 1.386 (3) |
C10—C11 | 1.392 (3) | C25—H25 | 0.9500 |
C10—H10 | 0.9500 | C26—C27 | 1.381 (3) |
C11—H11 | 0.9500 | C26—H26 | 0.9500 |
C12—C17 | 1.396 (3) | C27—C28 | 1.385 (3) |
C12—C13 | 1.397 (3) | C28—C29 | 1.384 (3) |
C13—C14 | 1.388 (3) | C28—H28 | 0.9500 |
C13—H13 | 0.9500 | C29—H29 | 0.9500 |
O1—C1—C2 | 126.91 (16) | C16—C15—H15 | 120.0 |
O1—C1—C5 | 126.30 (17) | C15—C16—C17 | 119.96 (18) |
C2—C1—C5 | 106.78 (15) | C15—C16—H16 | 120.0 |
C3—C2—C12 | 130.15 (17) | C17—C16—H16 | 120.0 |
C3—C2—C1 | 106.79 (15) | C16—C17—C12 | 120.68 (17) |
C12—C2—C1 | 123.06 (15) | C16—C17—H17 | 119.7 |
C2—C3—C18 | 128.82 (16) | C12—C17—H17 | 119.7 |
C2—C3—C4 | 109.77 (16) | C23—C18—C19 | 118.60 (16) |
C18—C3—C4 | 121.41 (15) | C23—C18—C3 | 119.83 (16) |
C5—C4—C24 | 127.24 (16) | C19—C18—C3 | 121.56 (16) |
C5—C4—C3 | 110.06 (15) | C20—C19—C18 | 121.17 (16) |
C24—C4—C3 | 122.44 (15) | C20—C19—H19 | 119.4 |
C4—C5—C6 | 130.49 (16) | C18—C19—H19 | 119.4 |
C4—C5—C1 | 106.56 (15) | C21—C20—C19 | 118.40 (17) |
C6—C5—C1 | 122.44 (15) | C21—C20—H20 | 120.8 |
C11—C6—C7 | 118.40 (17) | C19—C20—H20 | 120.8 |
C11—C6—C5 | 120.93 (16) | C22—C21—C20 | 121.80 (17) |
C7—C6—C5 | 120.62 (16) | C22—C21—Br1 | 117.45 (13) |
C8—C7—C6 | 120.76 (17) | C20—C21—Br1 | 120.75 (14) |
C8—C7—H7 | 119.6 | C21—C22—C23 | 119.32 (17) |
C6—C7—H7 | 119.6 | C21—C22—H22 | 120.3 |
C7—C8—C9 | 120.38 (18) | C23—C22—H22 | 120.3 |
C7—C8—H8 | 119.8 | C22—C23—C18 | 120.71 (17) |
C9—C8—H8 | 119.8 | C22—C23—H23 | 119.6 |
C10—C9—C8 | 119.55 (18) | C18—C23—H23 | 119.6 |
C10—C9—H9 | 120.2 | C29—C24—C25 | 118.80 (16) |
C8—C9—H9 | 120.2 | C29—C24—C4 | 121.12 (16) |
C9—C10—C11 | 120.43 (18) | C25—C24—C4 | 119.98 (16) |
C9—C10—H10 | 119.8 | C26—C25—C24 | 121.12 (17) |
C11—C10—H10 | 119.8 | C26—C25—H25 | 119.4 |
C10—C11—C6 | 120.49 (17) | C24—C25—H25 | 119.4 |
C10—C11—H11 | 119.8 | C27—C26—C25 | 118.67 (17) |
C6—C11—H11 | 119.8 | C27—C26—H26 | 120.7 |
C17—C12—C13 | 118.57 (16) | C25—C26—H26 | 120.7 |
C17—C12—C2 | 121.74 (16) | C26—C27—C28 | 121.49 (16) |
C13—C12—C2 | 119.66 (16) | C26—C27—Br2 | 119.80 (14) |
C14—C13—C12 | 120.64 (17) | C28—C27—Br2 | 118.67 (14) |
C14—C13—H13 | 119.7 | C29—C28—C27 | 119.46 (17) |
C12—C13—H13 | 119.7 | C29—C28—H28 | 120.3 |
C15—C14—C13 | 120.14 (17) | C27—C28—H28 | 120.3 |
C15—C14—H14 | 119.9 | C28—C29—C24 | 120.42 (17) |
C13—C14—H14 | 119.9 | C28—C29—H29 | 119.8 |
C14—C15—C16 | 119.99 (17) | C24—C29—H29 | 119.8 |
C14—C15—H15 | 120.0 | ||
O1—C1—C2—C3 | −179.45 (18) | C17—C12—C13—C14 | −1.1 (3) |
C5—C1—C2—C3 | 1.50 (19) | C2—C12—C13—C14 | 176.79 (17) |
O1—C1—C2—C12 | 0.1 (3) | C12—C13—C14—C15 | −0.2 (3) |
C5—C1—C2—C12 | −178.90 (15) | C13—C14—C15—C16 | 1.0 (3) |
C12—C2—C3—C18 | −0.8 (3) | C14—C15—C16—C17 | −0.4 (3) |
C1—C2—C3—C18 | 178.75 (17) | C15—C16—C17—C12 | −0.9 (3) |
C12—C2—C3—C4 | 178.56 (17) | C13—C12—C17—C16 | 1.7 (3) |
C1—C2—C3—C4 | −1.88 (19) | C2—C12—C17—C16 | −176.19 (17) |
C2—C3—C4—C5 | 1.7 (2) | C2—C3—C18—C23 | −126.7 (2) |
C18—C3—C4—C5 | −178.89 (16) | C4—C3—C18—C23 | 54.0 (2) |
C2—C3—C4—C24 | −172.90 (16) | C2—C3—C18—C19 | 54.6 (3) |
C18—C3—C4—C24 | 6.5 (2) | C4—C3—C18—C19 | −124.71 (18) |
C24—C4—C5—C6 | 1.8 (3) | C23—C18—C19—C20 | −0.2 (3) |
C3—C4—C5—C6 | −172.48 (17) | C3—C18—C19—C20 | 178.54 (16) |
C24—C4—C5—C1 | 173.62 (16) | C18—C19—C20—C21 | 0.5 (3) |
C3—C4—C5—C1 | −0.63 (19) | C19—C20—C21—C22 | −0.5 (3) |
O1—C1—C5—C4 | −179.53 (18) | C19—C20—C21—Br1 | −179.71 (13) |
C2—C1—C5—C4 | −0.47 (19) | C20—C21—C22—C23 | 0.2 (3) |
O1—C1—C5—C6 | −6.9 (3) | Br1—C21—C22—C23 | 179.40 (14) |
C2—C1—C5—C6 | 172.18 (16) | C21—C22—C23—C18 | 0.2 (3) |
C4—C5—C6—C11 | −147.57 (19) | C19—C18—C23—C22 | −0.2 (3) |
C1—C5—C6—C11 | 41.7 (3) | C3—C18—C23—C22 | −178.92 (17) |
C4—C5—C6—C7 | 35.0 (3) | C5—C4—C24—C29 | 56.6 (3) |
C1—C5—C6—C7 | −135.76 (18) | C3—C4—C24—C29 | −129.80 (18) |
C11—C6—C7—C8 | 0.3 (3) | C5—C4—C24—C25 | −119.9 (2) |
C5—C6—C7—C8 | 177.85 (16) | C3—C4—C24—C25 | 53.7 (2) |
C6—C7—C8—C9 | 0.2 (3) | C29—C24—C25—C26 | −2.1 (3) |
C7—C8—C9—C10 | −0.3 (3) | C4—C24—C25—C26 | 174.47 (17) |
C8—C9—C10—C11 | 0.0 (3) | C24—C25—C26—C27 | 1.1 (3) |
C9—C10—C11—C6 | 0.5 (3) | C25—C26—C27—C28 | 0.3 (3) |
C7—C6—C11—C10 | −0.7 (3) | C25—C26—C27—Br2 | −177.38 (13) |
C5—C6—C11—C10 | −178.20 (16) | C26—C27—C28—C29 | −0.8 (3) |
C3—C2—C12—C17 | 35.5 (3) | Br2—C27—C28—C29 | 176.94 (13) |
C1—C2—C12—C17 | −144.03 (18) | C27—C28—C29—C24 | −0.2 (3) |
C3—C2—C12—C13 | −142.4 (2) | C25—C24—C29—C28 | 1.6 (3) |
C1—C2—C12—C13 | 38.1 (2) | C4—C24—C29—C28 | −174.91 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
C28—H28···Br1i | 0.95 | 2.87 | 3.6920 (18) | 146 |
C22—H22···Br2ii | 0.95 | 2.97 | 3.6386 (19) | 129 |
C15—H15···Br1iii | 0.95 | 3.03 | 3.8556 (18) | 146 |
Symmetry codes: (i) x+1, y, z; (ii) −x+2, y−1/2, −z+1/2; (iii) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C29H18Br2O |
Mr | 542.25 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 93 |
a, b, c (Å) | 10.0677 (4), 9.6526 (4), 23.6791 (9) |
β (°) | 99.193 (2) |
V (Å3) | 2271.57 (16) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 3.59 |
Crystal size (mm) | 0.20 × 0.19 × 0.18 |
Data collection | |
Diffractometer | Bruker KappaCCD APEXII area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2004) |
Tmin, Tmax | 0.534, 0.564 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21955, 3999, 3578 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.019, 0.047, 1.06 |
No. of reflections | 3999 |
No. of parameters | 289 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.26 |
Computer programs: APEX2 (Bruker, YEAR?), SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXTL (Sheldrick, 2001), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
C28—H28···Br1i | 0.95 | 2.87 | 3.6920 (18) | 146.0 |
C22—H22···Br2ii | 0.95 | 2.97 | 3.6386 (19) | 128.8 |
C15—H15···Br1iii | 0.95 | 3.03 | 3.8556 (18) | 145.9 |
Symmetry codes: (i) x+1, y, z; (ii) −x+2, y−1/2, −z+1/2; (iii) −x+1, −y+1, −z+1. |
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The molecular geometry is best described by a paddle-wheel fashion, due to steric hindrance of the neighbouring aryl rings. The crystal packing is dominated by intramolecular C—H···π interactions. These intermolecular contacts, where π is an aromatic-ring centroid, with H···π distances ranging from 2.67 to 2.90 Å give rise to the formation of molecular chains extended along the a and b axis. Furthermore, unusual C—H···Br contacts forming a three-dimensional network can be observed (Figure 2).