organic compounds
The title compound, C22H24Br2O2, consists of two substituted tetralin units that are connected through a C-C single bond; the aromatic rings are twisted by 80.2 (2)°.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680605536X/ci2257sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680605536X/ci2257Isup2.hkl |
CCDC reference: 636201
Computing details top
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2006).
(S)-3,3'-Dibromo-5,5',6,6',7,7',8,8'-octahydro-2,2'-dimethoxy-1,1'-
binaphthalene top
Crystal data top
C22H24Br2O2 | F(000) = 968 |
Mr = 480.23 | Dx = 1.513 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 3469 reflections |
a = 10.004 (1) Å | θ = 2.3–23.2° |
b = 12.086 (1) Å | µ = 3.86 mm−1 |
c = 17.434 (2) Å | T = 295 K |
V = 2107.9 (4) Å3 | Block, colourless |
Z = 4 | 0.26 × 0.20 × 0.12 mm |
Data collection top
Bruker SMART 1K area-detector diffractometer | 4338 independent reflections |
Radiation source: fine-focus sealed tube | 2993 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
φ and ω scans | θmax = 26.5°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→11 |
Tmin = 0.434, Tmax = 0.655 | k = −15→8 |
11804 measured reflections | l = −20→21 |
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)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.114 | w = 1/[σ2(Fo2) + (0.0603P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max = 0.001 |
4338 reflections | Δρmax = 0.61 e Å−3 |
242 parameters | Δρmin = −0.34 e Å−3 |
23 restraints | Absolute structure: Flack (1983), with 1858 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.01 (2) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Br1 | 0.34571 (6) | 0.65682 (5) | 0.07420 (4) | 0.0577 (2) | |
Br2 | 0.06806 (7) | 1.09239 (6) | 0.41225 (4) | 0.0686 (2) | |
O1 | 0.1877 (3) | 0.8488 (3) | 0.1464 (2) | 0.0465 (9) | |
O2 | 0.2556 (4) | 0.9404 (3) | 0.3193 (2) | 0.0534 (10) | |
C1 | 0.3709 (5) | 0.9718 (4) | 0.1720 (3) | 0.0383 (12) | |
C2 | 0.3228 (5) | 0.8721 (4) | 0.1430 (3) | 0.0362 (13) | |
C3 | 0.4119 (5) | 0.7933 (5) | 0.1134 (3) | 0.0423 (3) | |
C4 | 0.5514 (6) | 0.8152 (5) | 0.1130 (3) | 0.0470 (14) | |
H4 | 0.6103 | 0.7620 | 0.0945 | 0.056* | |
C5 | 0.6016 (4) | 0.9174 (5) | 0.1405 (3) | 0.0443 (14) | |
C6 | 0.5141 (5) | 0.9958 (4) | 0.1713 (3) | 0.0393 (13) | |
C7 | 0.5659 (4) | 1.1024 (4) | 0.2041 (4) | 0.0556 (15) | |
H7C | 0.5477 | 1.1621 | 0.1684 | 0.067* | 0.37 (1) |
H7D | 0.5189 | 1.1185 | 0.2515 | 0.067* | 0.37 (1) |
H7A | 0.5115 | 1.1626 | 0.1845 | 0.067* | 0.63 (1) |
H7B | 0.5556 | 1.1011 | 0.2594 | 0.067* | 0.63 (1) |
C8' | 0.7129 (6) | 1.0979 (13) | 0.2197 (9) | 0.070 (4) | 0.37 (1) |
H8'A | 0.7296 | 1.0508 | 0.2637 | 0.084* | 0.37 (1) |
H8'B | 0.7454 | 1.1715 | 0.2317 | 0.084* | 0.37 (1) |
C9' | 0.7864 (11) | 1.0536 (8) | 0.1513 (11) | 0.091 (5) | 0.37 (1) |
H9'A | 0.7632 | 1.0966 | 0.1062 | 0.109* | 0.37 (1) |
H9'B | 0.8819 | 1.0602 | 0.1595 | 0.109* | 0.37 (1) |
C8 | 0.7090 (6) | 1.1265 (6) | 0.1863 (7) | 0.070 (4) | 0.63 |
H8A | 0.7146 | 1.1587 | 0.1354 | 0.084* | 0.63 (1) |
H8B | 0.7421 | 1.1808 | 0.2226 | 0.084* | 0.63 (1) |
C9 | 0.7963 (7) | 1.0265 (7) | 0.1894 (7) | 0.091 (5) | 0.63 |
H9A | 0.8864 | 1.0475 | 0.1749 | 0.109* | 0.63 (1) |
H9B | 0.7993 | 0.9997 | 0.2418 | 0.109* | 0.63 (1) |
C10 | 0.7507 (4) | 0.9348 (5) | 0.1385 (4) | 0.0632 (18) | |
H10C | 0.7925 | 0.8898 | 0.1778 | 0.076* | 0.37 (1) |
H10D | 0.7851 | 0.9112 | 0.0891 | 0.076* | 0.37 (1) |
H10A | 0.7952 | 0.8667 | 0.1532 | 0.076* | 0.63 (1) |
H10B | 0.7774 | 0.9524 | 0.0864 | 0.076* | 0.63 (1) |
C11 | 0.2716 (5) | 1.0543 (4) | 0.2041 (3) | 0.0419 (13) | |
C12 | 0.2218 (5) | 1.0358 (4) | 0.2787 (3) | 0.0410 (13) | |
C13 | 0.1273 (5) | 1.1101 (5) | 0.3086 (3) | 0.0458 (15) | |
C14 | 0.0823 (6) | 1.1974 (5) | 0.2647 (4) | 0.0492 (15) | |
H14 | 0.0194 | 1.2455 | 0.2853 | 0.059* | |
C15 | 0.1283 (5) | 1.2156 (5) | 0.1901 (3) | 0.0489 (15) | |
C16 | 0.2290 (5) | 1.1461 (5) | 0.1594 (3) | 0.0463 (13) | |
C17 | 0.2845 (6) | 1.1636 (5) | 0.0799 (3) | 0.0622 (16) | |
H17A | 0.3812 | 1.1593 | 0.0824 | 0.075* | |
H17B | 0.2539 | 1.1038 | 0.0473 | 0.075* | |
C18 | 0.2471 (10) | 1.2696 (8) | 0.0441 (5) | 0.168 (6) | |
H18A | 0.3141 | 1.3241 | 0.0578 | 0.201* | |
H18B | 0.2508 | 1.2603 | −0.0111 | 0.201* | |
C19 | 0.1159 (10) | 1.3149 (9) | 0.0636 (4) | 0.157 (5) | |
H19A | 0.0491 | 1.2750 | 0.0342 | 0.188* | |
H19B | 0.1134 | 1.3914 | 0.0468 | 0.188* | |
C20 | 0.0759 (7) | 1.3116 (6) | 0.1452 (3) | 0.069 (2) | |
H20A | −0.0209 | 1.3106 | 0.1478 | 0.083* | |
H20B | 0.1060 | 1.3793 | 0.1696 | 0.083* | |
C21 | 0.1145 (5) | 0.8788 (5) | 0.0780 (4) | 0.0606 (17) | |
H21A | 0.0220 | 0.8601 | 0.0843 | 0.091* | |
H21B | 0.1504 | 0.8394 | 0.0348 | 0.091* | |
H21C | 0.1228 | 0.9570 | 0.0693 | 0.091* | |
C22 | 0.3771 (7) | 0.9458 (7) | 0.3620 (4) | 0.077 (2) | |
H22A | 0.3925 | 0.8762 | 0.3870 | 0.116* | |
H22B | 0.3707 | 1.0034 | 0.3997 | 0.116* | |
H22C | 0.4500 | 0.9615 | 0.3278 | 0.116* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0614 (4) | 0.0468 (3) | 0.0649 (4) | −0.0006 (3) | −0.0027 (3) | −0.0137 (3) |
Br2 | 0.0718 (4) | 0.0710 (4) | 0.0629 (5) | −0.0048 (4) | 0.0262 (4) | −0.0171 (4) |
O1 | 0.0295 (19) | 0.061 (2) | 0.049 (2) | −0.0021 (19) | 0.0018 (16) | −0.001 (2) |
O2 | 0.046 (2) | 0.053 (2) | 0.061 (3) | −0.003 (2) | 0.005 (2) | 0.001 (2) |
C1 | 0.034 (3) | 0.042 (3) | 0.038 (3) | 0.007 (2) | 0.004 (2) | −0.003 (2) |
C2 | 0.029 (3) | 0.043 (3) | 0.037 (3) | 0.002 (2) | 0.005 (2) | 0.002 (2) |
C3 | 0.048 (3) | 0.044 (3) | 0.035 (3) | 0.007 (3) | −0.001 (2) | −0.005 (2) |
C4 | 0.041 (3) | 0.049 (4) | 0.051 (4) | 0.011 (3) | 0.000 (3) | −0.011 (3) |
C5 | 0.032 (3) | 0.056 (4) | 0.045 (3) | 0.007 (3) | 0.000 (2) | −0.003 (3) |
C6 | 0.037 (3) | 0.043 (3) | 0.038 (3) | 0.000 (2) | 0.001 (2) | 0.001 (2) |
C7 | 0.049 (3) | 0.052 (3) | 0.066 (4) | −0.005 (3) | 0.007 (3) | −0.009 (3) |
C8' | 0.062 (5) | 0.078 (8) | 0.069 (9) | −0.027 (5) | 0.020 (5) | −0.018 (7) |
C9' | 0.031 (4) | 0.094 (9) | 0.147 (15) | 0.003 (5) | −0.027 (6) | −0.014 (9) |
C8 | 0.062 (5) | 0.078 (8) | 0.069 (9) | −0.027 (5) | 0.020 (5) | −0.018 (7) |
C9 | 0.031 (4) | 0.094 (9) | 0.147 (15) | 0.003 (5) | −0.027 (6) | −0.014 (9) |
C10 | 0.037 (3) | 0.074 (5) | 0.078 (5) | 0.003 (3) | 0.004 (3) | −0.010 (4) |
C11 | 0.040 (3) | 0.040 (3) | 0.046 (3) | 0.003 (3) | 0.001 (3) | −0.008 (2) |
C12 | 0.035 (3) | 0.037 (3) | 0.051 (4) | −0.004 (2) | −0.001 (3) | −0.005 (2) |
C13 | 0.040 (3) | 0.051 (4) | 0.047 (3) | −0.003 (3) | 0.005 (3) | −0.020 (3) |
C14 | 0.035 (3) | 0.049 (4) | 0.063 (4) | 0.006 (3) | 0.004 (3) | −0.023 (3) |
C15 | 0.041 (3) | 0.045 (3) | 0.061 (4) | 0.010 (3) | −0.007 (3) | −0.015 (3) |
C16 | 0.039 (3) | 0.047 (3) | 0.053 (4) | 0.002 (3) | −0.001 (3) | −0.007 (3) |
C17 | 0.064 (4) | 0.071 (4) | 0.051 (4) | 0.004 (3) | 0.005 (3) | 0.005 (4) |
C18 | 0.230 (14) | 0.159 (10) | 0.114 (8) | 0.114 (11) | 0.061 (9) | 0.076 (8) |
C19 | 0.162 (10) | 0.166 (10) | 0.142 (10) | 0.109 (9) | 0.016 (8) | 0.067 (8) |
C20 | 0.071 (4) | 0.068 (5) | 0.068 (5) | 0.028 (4) | −0.005 (4) | −0.003 (3) |
C21 | 0.045 (3) | 0.073 (4) | 0.064 (4) | −0.003 (3) | −0.009 (3) | 0.006 (3) |
C22 | 0.068 (5) | 0.092 (6) | 0.072 (5) | 0.003 (4) | −0.013 (4) | 0.018 (4) |
Geometric parameters (Å, º) top
Br1—C3 | 1.904 (6) | C9—H9A | 0.97 |
Br2—C13 | 1.914 (6) | C9—H9B | 0.97 |
O1—C2 | 1.382 (6) | C10—H10C | 0.97 |
O1—C21 | 1.446 (7) | C10—H10D | 0.97 |
O2—C12 | 1.394 (6) | C10—H10A | 0.97 |
O2—C22 | 1.427 (7) | C10—H10B | 0.97 |
C1—C2 | 1.393 (7) | C11—C12 | 1.411 (7) |
C1—C6 | 1.461 (7) | C11—C16 | 1.421 (7) |
C1—C11 | 1.515 (7) | C12—C13 | 1.404 (7) |
C2—C3 | 1.403 (7) | C13—C14 | 1.379 (8) |
C3—C4 | 1.420 (8) | C14—C15 | 1.396 (8) |
C4—C5 | 1.417 (8) | C14—H14 | 0.93 |
C4—H4 | 0.93 | C15—C16 | 1.417 (7) |
C5—C6 | 1.397 (7) | C15—C20 | 1.495 (8) |
C5—C10 | 1.507 (4) | C16—C17 | 1.507 (8) |
C6—C7 | 1.503 (4) | C17—C18 | 1.474 (5) |
C7—C8 | 1.494 (5) | C17—H17A | 0.97 |
C7—C8' | 1.497 (5) | C17—H17B | 0.97 |
C7—H7C | 0.97 | C18—C19 | 1.462 (5) |
C7—H7D | 0.97 | C18—H18A | 0.97 |
C7—H7A | 0.97 | C18—H18B | 0.97 |
C7—H7B | 0.97 | C19—C20 | 1.477 (5) |
C8'—C9' | 1.500 (5) | C19—H19A | 0.97 |
C8'—H8'A | 0.97 | C19—H19B | 0.97 |
C8'—H8'B | 0.97 | C20—H20A | 0.97 |
C9'—C10 | 1.496 (5) | C20—H20B | 0.97 |
C9'—H9'A | 0.97 | C21—H21A | 0.96 |
C9'—H9'B | 0.97 | C21—H21B | 0.96 |
C8—C9 | 1.492 (5) | C21—H21C | 0.96 |
C8—H8A | 0.97 | C22—H22A | 0.96 |
C8—H8B | 0.97 | C22—H22B | 0.96 |
C9—C10 | 1.491 (5) | C22—H22C | 0.96 |
C2—O1—C21 | 114.0 (4) | C5—C10—H10D | 109.3 |
C12—O2—C22 | 115.7 (5) | H10C—C10—H10D | 108.0 |
C2—C1—C6 | 120.5 (5) | C9—C10—H10A | 109.5 |
C2—C1—C11 | 118.5 (4) | C5—C10—H10A | 109.2 |
C6—C1—C11 | 121.0 (5) | C9—C10—H10B | 108.1 |
O1—C2—C1 | 119.9 (4) | C5—C10—H10B | 109.0 |
O1—C2—C3 | 119.9 (5) | H10A—C10—H10B | 107.9 |
C1—C2—C3 | 120.1 (5) | C12—C11—C16 | 121.6 (5) |
C2—C3—C4 | 120.0 (5) | C12—C11—C1 | 117.9 (5) |
C2—C3—Br1 | 120.0 (4) | C16—C11—C1 | 120.5 (5) |
C4—C3—Br1 | 120.1 (4) | O2—C12—C13 | 120.3 (5) |
C5—C4—C3 | 120.6 (5) | O2—C12—C11 | 120.9 (5) |
C5—C4—H4 | 119.7 | C13—C12—C11 | 118.6 (5) |
C3—C4—H4 | 119.7 | C14—C13—C12 | 120.2 (5) |
C6—C5—C4 | 119.9 (4) | C14—C13—Br2 | 120.6 (4) |
C6—C5—C10 | 122.3 (4) | C12—C13—Br2 | 119.2 (5) |
C4—C5—C10 | 117.7 (5) | C13—C14—C15 | 122.0 (5) |
C5—C6—C1 | 118.9 (4) | C13—C14—H14 | 119.0 |
C5—C6—C7 | 120.8 (4) | C15—C14—H14 | 119.0 |
C1—C6—C7 | 120.3 (4) | C14—C15—C16 | 119.5 (5) |
C8—C7—C6 | 114.8 (4) | C14—C15—C20 | 119.7 (5) |
C8'—C7—C6 | 112.1 (5) | C16—C15—C20 | 120.7 (5) |
C8'—C7—H7C | 109.2 | C15—C16—C11 | 117.9 (5) |
C6—C7—H7C | 109.2 | C15—C16—C17 | 121.8 (5) |
C8'—C7—H7D | 109.2 | C11—C16—C17 | 120.2 (5) |
C6—C7—H7D | 109.2 | C18—C17—C16 | 114.7 (5) |
H7C—C7—H7D | 107.9 | C18—C17—H17A | 108.6 |
C8—C7—H7A | 108.6 | C16—C17—H17A | 108.6 |
C6—C7—H7A | 108.3 | C18—C17—H17B | 108.6 |
C8—C7—H7B | 108.1 | C16—C17—H17B | 108.6 |
C6—C7—H7B | 109.1 | H17A—C17—H17B | 107.6 |
H7A—C7—H7B | 107.7 | C19—C18—C17 | 117.0 (6) |
C7—C8'—C9' | 110.4 (7) | C19—C18—H18A | 108.0 |
C7—C8'—H8'A | 109.6 | C17—C18—H18A | 108.0 |
C9'—C8'—H8'A | 109.6 | C19—C18—H18B | 108.0 |
C7—C8'—H8'B | 109.6 | C17—C18—H18B | 108.0 |
C9'—C8'—H8'B | 109.6 | H18A—C18—H18B | 107.3 |
H8'A—C8'—H8'B | 108.1 | C18—C19—C20 | 117.2 (5) |
C10—C9'—C8' | 110.2 (7) | C18—C19—H19A | 108.0 |
C10—C9'—H9'A | 109.6 | C20—C19—H19A | 108.0 |
C8'—C9'—H9'A | 109.6 | C18—C19—H19B | 108.0 |
C10—C9'—H9'B | 109.6 | C20—C19—H19B | 108.0 |
C8'—C9'—H9'B | 109.6 | H19A—C19—H19B | 107.2 |
H9'A—C9'—H9'B | 108.1 | C19—C20—C15 | 115.5 (5) |
C9—C8—C7 | 113.3 (6) | C19—C20—H20A | 108.4 |
C9—C8—H8A | 108.9 | C15—C20—H20A | 108.4 |
C7—C8—H8A | 108.9 | C19—C20—H20B | 108.4 |
C9—C8—H8B | 108.9 | C15—C20—H20B | 108.4 |
C7—C8—H8B | 108.9 | H20A—C20—H20B | 107.5 |
H8A—C8—H8B | 107.7 | O1—C21—H21A | 109.5 |
C10—C9—C8 | 113.7 (6) | O1—C21—H21B | 109.5 |
C10—C9—H9A | 108.8 | H21A—C21—H21B | 109.5 |
C8—C9—H9A | 108.8 | O1—C21—H21C | 109.5 |
C10—C9—H9B | 108.8 | H21A—C21—H21C | 109.5 |
C8—C9—H9B | 108.8 | H21B—C21—H21C | 109.5 |
H9A—C9—H9B | 107.7 | O2—C22—H22A | 109.5 |
C9—C10—C5 | 113.1 (5) | O2—C22—H22B | 109.5 |
C9'—C10—C5 | 111.5 (5) | H22A—C22—H22B | 109.5 |
C9'—C10—H10C | 109.3 | O2—C22—H22C | 109.5 |
C5—C10—H10C | 109.3 | H22A—C22—H22C | 109.5 |
C9—C10—H10D | 129.7 | H22B—C22—H22C | 109.5 |
C9'—C10—H10D | 109.3 | ||
C21—O1—C2—C1 | 93.9 (6) | C6—C5—C10—C9' | −16.3 (11) |
C21—O1—C2—C3 | −89.0 (6) | C4—C5—C10—C9' | 166.5 (9) |
C6—C1—C2—O1 | 177.7 (5) | C2—C1—C11—C12 | 79.0 (6) |
C11—C1—C2—O1 | −2.3 (7) | C6—C1—C11—C12 | −101.0 (6) |
C6—C1—C2—C3 | 0.6 (8) | C2—C1—C11—C16 | −99.9 (6) |
C11—C1—C2—C3 | −179.4 (5) | C6—C1—C11—C16 | 80.1 (7) |
O1—C2—C3—C4 | −177.2 (5) | C22—O2—C12—C13 | −99.8 (6) |
C1—C2—C3—C4 | 0.0 (8) | C22—O2—C12—C11 | 86.3 (6) |
O1—C2—C3—Br1 | 2.6 (7) | C16—C11—C12—O2 | 174.4 (5) |
C1—C2—C3—Br1 | 179.7 (4) | C1—C11—C12—O2 | −4.6 (7) |
C2—C3—C4—C5 | −1.6 (8) | C16—C11—C12—C13 | 0.4 (8) |
Br1—C3—C4—C5 | 178.7 (4) | C1—C11—C12—C13 | −178.5 (5) |
C3—C4—C5—C6 | 2.6 (8) | O2—C12—C13—C14 | −172.3 (5) |
C3—C4—C5—C10 | 179.9 (6) | C11—C12—C13—C14 | 1.7 (7) |
C4—C5—C6—C1 | −2.0 (8) | O2—C12—C13—Br2 | 10.4 (6) |
C10—C5—C6—C1 | −179.2 (6) | C11—C12—C13—Br2 | −175.6 (4) |
C4—C5—C6—C7 | 177.2 (5) | C12—C13—C14—C15 | −0.3 (8) |
C10—C5—C6—C7 | 0.0 (9) | Br2—C13—C14—C15 | 177.0 (4) |
C2—C1—C6—C5 | 0.5 (8) | C13—C14—C15—C16 | −3.2 (8) |
C11—C1—C6—C5 | −179.6 (5) | C13—C14—C15—C20 | −180.0 (6) |
C2—C1—C6—C7 | −178.7 (5) | C14—C15—C16—C11 | 5.1 (8) |
C11—C1—C6—C7 | 1.3 (8) | C20—C15—C16—C11 | −178.2 (5) |
C5—C6—C7—C8 | 12.2 (9) | C14—C15—C16—C17 | −178.6 (5) |
C1—C6—C7—C8 | −168.6 (7) | C20—C15—C16—C17 | −1.9 (8) |
C5—C6—C7—C8' | −16.3 (11) | C12—C11—C16—C15 | −3.8 (8) |
C1—C6—C7—C8' | 162.8 (9) | C1—C11—C16—C15 | 175.1 (5) |
C8—C7—C8'—C9' | −52.6 (9) | C12—C11—C16—C17 | 179.8 (5) |
C6—C7—C8'—C9' | 48.8 (13) | C1—C11—C16—C17 | −1.2 (8) |
C7—C8'—C9'—C10 | −66.8 (14) | C15—C16—C17—C18 | 12.0 (10) |
C6—C7—C8—C9 | −39.4 (11) | C11—C16—C17—C18 | −171.8 (8) |
C7—C8—C9—C10 | 55.8 (13) | C16—C17—C18—C19 | −32.5 (13) |
C8—C9—C10—C5 | −42.4 (12) | C17—C18—C19—C20 | 44.0 (15) |
C8'—C9'—C10—C5 | 48.4 (13) | C18—C19—C20—C15 | −32.2 (13) |
C6—C5—C10—C9 | 15.1 (10) | C14—C15—C20—C19 | −171.8 (8) |
C4—C5—C10—C9 | −162.2 (7) | C16—C15—C20—C19 | 11.5 (10) |