organic compounds
In the title compound, 2C14H18O5Br2·OH3+·Br3−, the two 15-crown-5 macrocylic rings are linked by an oxonium cation via O—HO hydrogen bonds, forming a positively charged unsymmetrical sandwich-like compound with a tribromide counter-anion. The conformations of the two crown-5 fragments have gauche C—C and anti C—O linkages.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806010932/at2019sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806010932/at2019Isup2.hkl |
CCDC reference: 604959
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.011 Å
- R factor = 0.053
- wR factor = 0.133
- Data-to-parameter ratio = 16.2
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT431_ALERT_2_B Short Inter HL..A Contact Br2 .. Br5 .. 3.39 Ang. PLAT731_ALERT_1_B Bond Calc 0.85(8), Rep 0.857(10) ...... 8.00 su-Rat O1W -H1W1 1.555 1.555 PLAT731_ALERT_1_B Bond Calc 0.86(6), Rep 0.855(10) ...... 6.00 su-Rat O1W -H1W2 1.555 1.555 PLAT731_ALERT_1_B Bond Calc 0.86(8), Rep 0.856(10) ...... 8.00 su-Rat O1W -H1W3 1.555 1.555
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C25 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Br6 PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........ O1W PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 11 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
0 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 7 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 3 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 2 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
Bis(2,3-dibromo-6,7,9,10,12,13,15,16-octahydro-5,8,11,14,17-pentaoxa-
benzocyclopentadecene)hydroxonium tribromide top
Crystal data top
2C14H18Br2O5·H3O+·Br3− | Z = 2 |
Mr = 1110.96 | F(000) = 1080 |
Triclinic, P1 | Dx = 1.882 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 12.568 (3) Å | Cell parameters from 957 reflections |
b = 13.590 (3) Å | θ = 1.6–25.0° |
c = 13.829 (3) Å | µ = 7.21 mm−1 |
α = 70.697 (4)° | T = 273 K |
β = 66.718 (4)° | Block, brown |
γ = 67.601 (4)° | 0.50 × 0.27 × 0.13 mm |
V = 1960.4 (7) Å3 |
Data collection top
Bruker SMART APEX area-detector diffractometer | 6883 independent reflections |
Radiation source: fine-focus sealed tube | 4087 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
Detector resolution: 83.66 pixels mm-1 | θmax = 25.0°, θmin = 1.6° |
ω scan | h = −14→14 |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | k = −16→16 |
Tmin = 0.104, Tmax = 0.392 | l = −16→16 |
18603 measured reflections |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0436P)2 + 5.5902P] where P = (Fo2 + 2Fc2)/3 |
6883 reflections | (Δ/σ)max < 0.001 |
424 parameters | Δρmax = 0.92 e Å−3 |
3 restraints | Δρmin = −0.85 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Br1 | 0.27174 (9) | 1.19269 (7) | 0.30653 (7) | 0.0860 (3) | |
Br2 | 0.12568 (7) | 1.04647 (7) | 0.27397 (7) | 0.0825 (3) | |
Br3 | 0.10061 (8) | 0.74471 (9) | 0.31334 (10) | 0.1102 (4) | |
Br4 | 0.26009 (9) | 0.50512 (9) | 0.23460 (9) | 0.0980 (3) | |
Br5 | 0.83572 (9) | 0.03572 (9) | 0.38698 (12) | 0.1244 (5) | |
Br6 | 0.73873 (8) | 0.16895 (8) | 0.24797 (9) | 0.1019 (4) | |
Br7 | 0.64108 (11) | 0.30648 (11) | 0.10678 (12) | 0.1290 (5) | |
O1 | 0.5575 (4) | 0.8285 (3) | 0.0667 (3) | 0.0484 (11) | |
O2 | 0.6880 (4) | 0.6153 (3) | 0.0668 (3) | 0.0483 (11) | |
O3 | 0.9199 (4) | 0.6567 (4) | 0.0188 (3) | 0.0557 (12) | |
O4 | 0.8970 (4) | 0.8230 (4) | 0.1162 (4) | 0.0607 (12) | |
O5 | 0.6672 (4) | 0.9373 (3) | 0.0938 (3) | 0.0534 (11) | |
O6 | 0.5997 (4) | 0.5179 (3) | 0.3552 (3) | 0.0481 (11) | |
O7 | 0.8516 (4) | 0.4672 (4) | 0.2795 (3) | 0.0519 (11) | |
O8 | 0.8392 (4) | 0.6288 (4) | 0.3765 (4) | 0.0659 (13) | |
O9 | 0.6284 (4) | 0.8189 (4) | 0.3829 (4) | 0.0625 (13) | |
O10 | 0.4810 (4) | 0.6989 (3) | 0.4133 (3) | 0.0534 (11) | |
O1W | 0.7219 (5) | 0.6991 (5) | 0.2153 (5) | 0.0701 (14) | |
H1W1 | 0.682 (6) | 0.703 (6) | 0.176 (5) | 0.084* | |
H1W2 | 0.751 (7) | 0.637 (3) | 0.252 (6) | 0.084* | |
H1W3 | 0.776 (5) | 0.732 (6) | 0.195 (6) | 0.084* | |
C1 | 0.5038 (6) | 0.7538 (5) | 0.0635 (5) | 0.0489 (16) | |
H1A | 0.4443 | 0.7915 | 0.0254 | 0.059* | |
H1B | 0.4645 | 0.7194 | 0.1359 | 0.059* | |
C2 | 0.6057 (6) | 0.6710 (5) | 0.0055 (5) | 0.0526 (17) | |
H2A | 0.5749 | 0.6197 | −0.0026 | 0.063* | |
H2B | 0.6467 | 0.7065 | −0.0657 | 0.063* | |
C3 | 0.8056 (6) | 0.5595 (6) | 0.0064 (6) | 0.062 (2) | |
H3A | 0.7973 | 0.5295 | −0.0440 | 0.075* | |
H3B | 0.8430 | 0.4992 | 0.0553 | 0.075* | |
C4 | 0.8864 (6) | 0.6316 (6) | −0.0543 (6) | 0.065 (2) | |
H4A | 0.9581 | 0.5950 | −0.1051 | 0.078* | |
H4B | 0.8445 | 0.6981 | −0.0946 | 0.078* | |
C5 | 0.9940 (6) | 0.7289 (6) | −0.0311 (6) | 0.067 (2) | |
H5A | 0.9561 | 0.7931 | −0.0766 | 0.081* | |
H5B | 1.0723 | 0.6930 | −0.0757 | 0.081* | |
C6 | 1.0091 (6) | 0.7609 (7) | 0.0544 (7) | 0.072 (2) | |
H6A | 1.0425 | 0.6959 | 0.1019 | 0.087* | |
H6B | 1.0660 | 0.8036 | 0.0215 | 0.087* | |
C7 | 0.8648 (7) | 0.9351 (6) | 0.0673 (7) | 0.070 (2) | |
H7A | 0.8807 | 0.9435 | −0.0092 | 0.084* | |
H7B | 0.9131 | 0.9710 | 0.0758 | 0.084* | |
C8 | 0.7343 (6) | 0.9859 (6) | 0.1183 (6) | 0.0595 (19) | |
H8A | 0.7165 | 0.9729 | 0.1956 | 0.071* | |
H8B | 0.7130 | 1.0639 | 0.0900 | 0.071* | |
C9 | 0.5449 (6) | 0.9697 (5) | 0.1363 (5) | 0.0458 (15) | |
C10 | 0.4799 (6) | 1.0531 (5) | 0.1911 (5) | 0.0528 (17) | |
H10A | 0.5195 | 1.0924 | 0.2016 | 0.063* | |
C11 | 0.3563 (7) | 1.0774 (5) | 0.2300 (5) | 0.0578 (19) | |
C12 | 0.2959 (6) | 1.0211 (5) | 0.2163 (5) | 0.0557 (18) | |
C13 | 0.3593 (6) | 0.9369 (5) | 0.1606 (5) | 0.0497 (16) | |
H13A | 0.3184 | 0.8990 | 0.1500 | 0.060* | |
C14 | 0.4841 (6) | 0.9106 (5) | 0.1214 (5) | 0.0446 (15) | |
C15 | 0.6738 (6) | 0.4201 (5) | 0.3173 (6) | 0.0504 (16) | |
H15A | 0.6893 | 0.4328 | 0.2403 | 0.061* | |
H15B | 0.6337 | 0.3634 | 0.3531 | 0.061* | |
C16 | 0.7888 (6) | 0.3872 (5) | 0.3417 (6) | 0.0573 (18) | |
H16A | 0.7722 | 0.3810 | 0.4179 | 0.069* | |
H16B | 0.8384 | 0.3168 | 0.3242 | 0.069* | |
C17 | 0.9427 (7) | 0.4631 (7) | 0.3184 (7) | 0.072 (2) | |
H17A | 1.0001 | 0.4980 | 0.2604 | 0.087* | |
H17B | 0.9860 | 0.3875 | 0.3402 | 0.087* | |
C18 | 0.8932 (8) | 0.5173 (7) | 0.4116 (7) | 0.078 (2) | |
H18A | 0.8336 | 0.4848 | 0.4695 | 0.094* | |
H18B | 0.9578 | 0.5081 | 0.4383 | 0.094* | |
C19 | 0.7859 (7) | 0.6885 (7) | 0.4590 (6) | 0.076 (2) | |
H19A | 0.8472 | 0.6837 | 0.4878 | 0.091* | |
H19B | 0.7248 | 0.6581 | 0.5171 | 0.091* | |
C20 | 0.7298 (8) | 0.8044 (7) | 0.4147 (6) | 0.075 (2) | |
H20A | 0.7036 | 0.8467 | 0.4688 | 0.090* | |
H20B | 0.7901 | 0.8322 | 0.3529 | 0.090* | |
C21 | 0.5176 (7) | 0.8245 (6) | 0.4683 (6) | 0.067 (2) | |
H21A | 0.4854 | 0.8951 | 0.4872 | 0.080* | |
H21B | 0.5309 | 0.7690 | 0.5314 | 0.080* | |
C22 | 0.4311 (6) | 0.8069 (5) | 0.4322 (5) | 0.0584 (19) | |
H22A | 0.3527 | 0.8147 | 0.4872 | 0.070* | |
H22B | 0.4211 | 0.8595 | 0.3666 | 0.070* | |
C23 | 0.4229 (5) | 0.6619 (5) | 0.3749 (5) | 0.0439 (15) | |
C24 | 0.3083 (6) | 0.7148 (5) | 0.3654 (5) | 0.0534 (17) | |
H24A | 0.2645 | 0.7810 | 0.3865 | 0.064* | |
C25 | 0.2588 (6) | 0.6680 (6) | 0.3238 (6) | 0.0581 (19) | |
C26 | 0.3222 (6) | 0.5722 (6) | 0.2926 (6) | 0.0577 (18) | |
C27 | 0.4369 (6) | 0.5185 (5) | 0.3016 (5) | 0.0516 (17) | |
H27A | 0.4798 | 0.4527 | 0.2796 | 0.062* | |
C28 | 0.4876 (5) | 0.5621 (5) | 0.3431 (5) | 0.0438 (15) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.1017 (7) | 0.0690 (5) | 0.0637 (5) | 0.0040 (5) | −0.0150 (5) | −0.0317 (4) |
Br2 | 0.0519 (5) | 0.0811 (6) | 0.0797 (6) | −0.0016 (4) | −0.0066 (4) | −0.0118 (5) |
Br3 | 0.0549 (5) | 0.1112 (8) | 0.1568 (10) | −0.0135 (5) | −0.0475 (6) | −0.0130 (7) |
Br4 | 0.0909 (7) | 0.1187 (8) | 0.1225 (8) | −0.0494 (6) | −0.0523 (6) | −0.0261 (6) |
Br5 | 0.0732 (7) | 0.0957 (8) | 0.1813 (12) | −0.0228 (6) | 0.0062 (7) | −0.0586 (8) |
Br6 | 0.0617 (5) | 0.1163 (8) | 0.1480 (9) | −0.0449 (5) | 0.0214 (5) | −0.0963 (7) |
Br7 | 0.1035 (8) | 0.1525 (11) | 0.1752 (12) | −0.0309 (7) | −0.0438 (8) | −0.0952 (10) |
O1 | 0.046 (3) | 0.048 (3) | 0.057 (3) | −0.016 (2) | −0.012 (2) | −0.019 (2) |
O2 | 0.051 (3) | 0.052 (3) | 0.046 (3) | −0.010 (2) | −0.019 (2) | −0.016 (2) |
O3 | 0.052 (3) | 0.066 (3) | 0.047 (3) | −0.025 (2) | −0.006 (2) | −0.014 (2) |
O4 | 0.053 (3) | 0.060 (3) | 0.071 (3) | −0.024 (2) | −0.012 (3) | −0.014 (3) |
O5 | 0.052 (3) | 0.052 (3) | 0.060 (3) | −0.021 (2) | −0.009 (2) | −0.019 (2) |
O6 | 0.041 (3) | 0.050 (3) | 0.057 (3) | −0.011 (2) | −0.014 (2) | −0.019 (2) |
O7 | 0.044 (3) | 0.065 (3) | 0.047 (3) | −0.018 (2) | −0.015 (2) | −0.009 (2) |
O8 | 0.072 (3) | 0.084 (4) | 0.053 (3) | −0.024 (3) | −0.025 (3) | −0.021 (3) |
O9 | 0.074 (3) | 0.075 (3) | 0.048 (3) | −0.033 (3) | −0.011 (3) | −0.020 (2) |
O10 | 0.058 (3) | 0.048 (3) | 0.057 (3) | −0.012 (2) | −0.016 (2) | −0.019 (2) |
O1W | 0.076 (4) | 0.080 (4) | 0.066 (4) | −0.034 (3) | −0.029 (3) | −0.006 (3) |
C1 | 0.049 (4) | 0.054 (4) | 0.050 (4) | −0.013 (3) | −0.023 (3) | −0.010 (3) |
C2 | 0.059 (4) | 0.059 (4) | 0.049 (4) | −0.016 (3) | −0.021 (4) | −0.019 (3) |
C3 | 0.055 (4) | 0.060 (4) | 0.080 (5) | −0.002 (4) | −0.024 (4) | −0.038 (4) |
C4 | 0.051 (4) | 0.089 (6) | 0.052 (5) | −0.015 (4) | −0.005 (4) | −0.028 (4) |
C5 | 0.049 (4) | 0.065 (5) | 0.068 (5) | −0.020 (4) | 0.002 (4) | −0.011 (4) |
C6 | 0.042 (4) | 0.077 (5) | 0.101 (7) | −0.023 (4) | −0.015 (4) | −0.023 (5) |
C7 | 0.063 (5) | 0.060 (5) | 0.090 (6) | −0.037 (4) | −0.011 (4) | −0.013 (4) |
C8 | 0.064 (5) | 0.052 (4) | 0.071 (5) | −0.029 (4) | −0.013 (4) | −0.019 (4) |
C9 | 0.048 (4) | 0.043 (4) | 0.041 (4) | −0.015 (3) | −0.009 (3) | −0.006 (3) |
C10 | 0.059 (5) | 0.047 (4) | 0.048 (4) | −0.012 (3) | −0.017 (4) | −0.008 (3) |
C11 | 0.073 (5) | 0.039 (4) | 0.047 (4) | −0.003 (4) | −0.016 (4) | −0.011 (3) |
C12 | 0.052 (4) | 0.045 (4) | 0.048 (4) | −0.001 (3) | −0.014 (3) | 0.001 (3) |
C13 | 0.047 (4) | 0.049 (4) | 0.048 (4) | −0.015 (3) | −0.016 (3) | −0.001 (3) |
C14 | 0.053 (4) | 0.038 (4) | 0.037 (4) | −0.011 (3) | −0.015 (3) | −0.002 (3) |
C15 | 0.050 (4) | 0.042 (4) | 0.059 (4) | −0.016 (3) | −0.016 (3) | −0.010 (3) |
C16 | 0.048 (4) | 0.048 (4) | 0.061 (5) | −0.005 (3) | −0.016 (4) | −0.005 (4) |
C17 | 0.052 (5) | 0.085 (6) | 0.090 (6) | −0.010 (4) | −0.035 (4) | −0.026 (5) |
C18 | 0.084 (6) | 0.098 (7) | 0.076 (6) | −0.012 (5) | −0.057 (5) | −0.024 (5) |
C19 | 0.077 (6) | 0.107 (7) | 0.066 (5) | −0.034 (5) | −0.033 (5) | −0.023 (5) |
C20 | 0.092 (6) | 0.094 (7) | 0.068 (5) | −0.047 (5) | −0.023 (5) | −0.031 (5) |
C21 | 0.087 (6) | 0.061 (5) | 0.055 (5) | −0.024 (4) | −0.009 (4) | −0.028 (4) |
C22 | 0.071 (5) | 0.051 (4) | 0.043 (4) | −0.017 (4) | −0.002 (4) | −0.017 (3) |
C23 | 0.038 (4) | 0.050 (4) | 0.039 (4) | −0.016 (3) | −0.005 (3) | −0.007 (3) |
C24 | 0.045 (4) | 0.049 (4) | 0.048 (4) | −0.013 (3) | −0.001 (3) | −0.005 (3) |
C25 | 0.037 (4) | 0.063 (5) | 0.064 (5) | −0.021 (4) | −0.012 (3) | 0.001 (4) |
C26 | 0.049 (4) | 0.070 (5) | 0.062 (5) | −0.032 (4) | −0.020 (4) | −0.002 (4) |
C27 | 0.047 (4) | 0.050 (4) | 0.058 (4) | −0.019 (3) | −0.009 (3) | −0.015 (3) |
C28 | 0.038 (4) | 0.052 (4) | 0.040 (4) | −0.022 (3) | −0.003 (3) | −0.008 (3) |
Geometric parameters (Å, º) top
Br1—C11 | 1.908 (6) | C6—H6B | 0.9700 |
Br2—C12 | 1.898 (7) | C7—C8 | 1.486 (9) |
Br3—C25 | 1.900 (7) | C7—H7A | 0.9700 |
Br4—C26 | 1.899 (7) | C7—H7B | 0.9700 |
Br5—Br6 | 2.516 (2) | C8—H8A | 0.9700 |
Br6—Br7 | 2.558 (2) | C8—H8B | 0.9700 |
O1—C14 | 1.375 (7) | C9—C10 | 1.378 (9) |
O1—C1 | 1.435 (7) | C9—C14 | 1.405 (8) |
O2—C2 | 1.425 (7) | C10—C11 | 1.370 (9) |
O2—C3 | 1.430 (7) | C10—H10A | 0.9300 |
O3—C4 | 1.411 (8) | C11—C12 | 1.360 (10) |
O3—C5 | 1.431 (8) | C12—C13 | 1.393 (9) |
O4—C7 | 1.417 (8) | C13—C14 | 1.382 (9) |
O4—C6 | 1.430 (8) | C13—H13A | 0.9300 |
O5—C9 | 1.357 (7) | C15—C16 | 1.483 (9) |
O5—C8 | 1.436 (7) | C15—H15A | 0.9700 |
O6—C28 | 1.359 (7) | C15—H15B | 0.9700 |
O6—C15 | 1.429 (7) | C16—H16A | 0.9700 |
O7—C17 | 1.422 (8) | C16—H16B | 0.9700 |
O7—C16 | 1.430 (7) | C17—C18 | 1.494 (10) |
O8—C18 | 1.409 (9) | C17—H17A | 0.9700 |
O8—C19 | 1.415 (8) | C17—H17B | 0.9700 |
O9—C21 | 1.420 (8) | C18—H18A | 0.9700 |
O9—C20 | 1.431 (8) | C18—H18B | 0.9700 |
O10—C23 | 1.353 (7) | C19—C20 | 1.487 (11) |
O10—C22 | 1.429 (7) | C19—H19A | 0.9700 |
O1W—H1W1 | 0.857 (10) | C19—H19B | 0.9700 |
O1W—H1W2 | 0.855 (10) | C20—H20A | 0.9700 |
O1W—H1W3 | 0.856 (10) | C20—H20B | 0.9700 |
C1—C2 | 1.496 (9) | C21—C22 | 1.481 (10) |
C1—H1A | 0.9700 | C21—H21A | 0.9700 |
C1—H1B | 0.9700 | C21—H21B | 0.9700 |
C2—H2A | 0.9700 | C22—H22A | 0.9700 |
C2—H2B | 0.9700 | C22—H22B | 0.9700 |
C3—C4 | 1.496 (10) | C23—C24 | 1.381 (9) |
C3—H3A | 0.9700 | C23—C28 | 1.402 (8) |
C3—H3B | 0.9700 | C24—C25 | 1.396 (9) |
C4—H4A | 0.9700 | C24—H24A | 0.9300 |
C4—H4B | 0.9700 | C25—C26 | 1.351 (10) |
C5—C6 | 1.484 (10) | C26—C27 | 1.380 (9) |
C5—H5A | 0.9700 | C27—C28 | 1.375 (8) |
C5—H5B | 0.9700 | C27—H27A | 0.9300 |
C6—H6A | 0.9700 | ||
Br5—Br6—Br7 | 179.21 (5) | C13—C12—Br2 | 116.1 (6) |
C14—O1—C1 | 118.1 (5) | C14—C13—C12 | 119.0 (6) |
C2—O2—C3 | 113.7 (5) | C14—C13—H13A | 120.5 |
C4—O3—C5 | 113.8 (5) | C12—C13—H13A | 120.5 |
C7—O4—C6 | 113.6 (6) | O1—C14—C13 | 124.9 (6) |
C9—O5—C8 | 117.0 (5) | O1—C14—C9 | 115.1 (5) |
C28—O6—C15 | 117.4 (5) | C13—C14—C9 | 120.0 (6) |
C17—O7—C16 | 113.9 (5) | O6—C15—C16 | 107.2 (5) |
C18—O8—C19 | 113.6 (6) | O6—C15—H15A | 110.3 |
C21—O9—C20 | 114.5 (5) | C16—C15—H15A | 110.3 |
C23—O10—C22 | 119.5 (5) | O6—C15—H15B | 110.3 |
H1W1—O1W—H1W2 | 119 (8) | C16—C15—H15B | 110.3 |
H1W1—O1W—H1W3 | 124 (8) | H15A—C15—H15B | 108.5 |
H1W2—O1W—H1W3 | 104 (8) | O7—C16—C15 | 109.0 (5) |
O1—C1—C2 | 105.8 (5) | O7—C16—H16A | 109.9 |
O1—C1—H1A | 110.6 | C15—C16—H16A | 109.9 |
C2—C1—H1A | 110.6 | O7—C16—H16B | 109.9 |
O1—C1—H1B | 110.6 | C15—C16—H16B | 109.9 |
C2—C1—H1B | 110.6 | H16A—C16—H16B | 108.3 |
H1A—C1—H1B | 108.7 | O7—C17—C18 | 113.0 (6) |
O2—C2—C1 | 108.3 (5) | O7—C17—H17A | 109.0 |
O2—C2—H2A | 110.0 | C18—C17—H17A | 109.0 |
C1—C2—H2A | 110.0 | O7—C17—H17B | 109.0 |
O2—C2—H2B | 110.0 | C18—C17—H17B | 109.0 |
C1—C2—H2B | 110.0 | H17A—C17—H17B | 107.8 |
H2A—C2—H2B | 108.4 | O8—C18—C17 | 108.4 (6) |
O2—C3—C4 | 112.9 (6) | O8—C18—H18A | 110.0 |
O2—C3—H3A | 109.0 | C17—C18—H18A | 110.0 |
C4—C3—H3A | 109.0 | O8—C18—H18B | 110.0 |
O2—C3—H3B | 109.0 | C17—C18—H18B | 110.0 |
C4—C3—H3B | 109.0 | H18A—C18—H18B | 108.4 |
H3A—C3—H3B | 107.8 | O8—C19—C20 | 109.6 (6) |
O3—C4—C3 | 109.4 (6) | O8—C19—H19A | 109.8 |
O3—C4—H4A | 109.8 | C20—C19—H19A | 109.8 |
C3—C4—H4A | 109.8 | O8—C19—H19B | 109.8 |
O3—C4—H4B | 109.8 | C20—C19—H19B | 109.8 |
C3—C4—H4B | 109.8 | H19A—C19—H19B | 108.2 |
H4A—C4—H4B | 108.2 | O9—C20—C19 | 112.8 (6) |
O3—C5—C6 | 108.7 (6) | O9—C20—H20A | 109.0 |
O3—C5—H5A | 110.0 | C19—C20—H20A | 109.0 |
C6—C5—H5A | 110.0 | O9—C20—H20B | 109.0 |
O3—C5—H5B | 110.0 | C19—C20—H20B | 109.0 |
C6—C5—H5B | 110.0 | H20A—C20—H20B | 107.8 |
H5A—C5—H5B | 108.3 | O9—C21—C22 | 108.4 (5) |
O4—C6—C5 | 112.0 (6) | O9—C21—H21A | 110.0 |
O4—C6—H6A | 109.2 | C22—C21—H21A | 110.0 |
C5—C6—H6A | 109.2 | O9—C21—H21B | 110.0 |
O4—C6—H6B | 109.2 | C22—C21—H21B | 110.0 |
C5—C6—H6B | 109.2 | H21A—C21—H21B | 108.4 |
H6A—C6—H6B | 107.9 | O10—C22—C21 | 106.5 (6) |
O4—C7—C8 | 109.6 (6) | O10—C22—H22A | 110.4 |
O4—C7—H7A | 109.7 | C21—C22—H22A | 110.4 |
C8—C7—H7A | 109.7 | O10—C22—H22B | 110.4 |
O4—C7—H7B | 109.7 | C21—C22—H22B | 110.4 |
C8—C7—H7B | 109.7 | H22A—C22—H22B | 108.6 |
H7A—C7—H7B | 108.2 | O10—C23—C24 | 125.0 (6) |
O5—C8—C7 | 107.2 (5) | O10—C23—C28 | 115.2 (5) |
O5—C8—H8A | 110.3 | C24—C23—C28 | 119.8 (6) |
C7—C8—H8A | 110.3 | C23—C24—C25 | 119.2 (6) |
O5—C8—H8B | 110.3 | C23—C24—H24A | 120.4 |
C7—C8—H8B | 110.3 | C25—C24—H24A | 120.4 |
H8A—C8—H8B | 108.5 | C26—C25—C24 | 120.6 (6) |
O5—C9—C10 | 125.2 (6) | C26—C25—Br3 | 122.2 (6) |
O5—C9—C14 | 115.0 (5) | C24—C25—Br3 | 117.2 (5) |
C10—C9—C14 | 119.8 (6) | C25—C26—C27 | 120.7 (6) |
C11—C10—C9 | 119.3 (6) | C25—C26—Br4 | 122.5 (5) |
C11—C10—H10A | 120.4 | C27—C26—Br4 | 116.8 (6) |
C9—C10—H10A | 120.4 | C28—C27—C26 | 120.0 (6) |
C12—C11—C10 | 121.7 (6) | C28—C27—H27A | 120.0 |
C12—C11—Br1 | 121.1 (6) | C26—C27—H27A | 120.0 |
C10—C11—Br1 | 117.2 (6) | O6—C28—C27 | 125.8 (6) |
C11—C12—C13 | 120.2 (6) | O6—C28—C23 | 114.6 (5) |
C11—C12—Br2 | 123.7 (5) | C27—C28—C23 | 119.6 (6) |
O5—C9—C14—O1 | 0.4 (8) | O10—C23—C28—O6 | −0.4 (8) |
C9—O5—C8—C7 | 177.8 (6) | C23—O10—C22—C21 | −177.3 (5) |
O4—C7—C8—O5 | −65.1 (8) | O9—C21—C22—O10 | 63.6 (7) |
C6—O4—C7—C8 | 163.4 (6) | C20—O9—C21—C22 | −163.7 (6) |
C7—O4—C6—C5 | −82.7 (8) | C21—O9—C20—C19 | 83.2 (8) |
O3—C5—C6—O4 | −64.9 (8) | O8—C19—C20—O9 | 66.6 (8) |
C4—O3—C5—C6 | 172.4 (6) | C18—O8—C19—C20 | −179.0 (6) |
C5—O3—C4—C3 | −177.8 (5) | C19—O8—C18—C17 | 178.4 (6) |
O2—C3—C4—O3 | 71.2 (7) | O7—C17—C18—O8 | −63.5 (9) |
C2—O2—C3—C4 | 84.8 (7) | C16—O7—C17—C18 | −80.2 (8) |
C3—O2—C2—C1 | −161.4 (5) | C17—O7—C16—C15 | 162.0 (6) |
O1—C1—C2—O2 | 62.5 (6) | O6—C15—C16—O7 | −65.6 (7) |
C14—O1—C1—C2 | −176.5 (5) | C28—O6—C15—C16 | −178.7 (5) |
C8—O5—C9—C14 | −172.5 (5) | C15—O6—C28—C23 | −175.7 (5) |
C8—O5—C9—C10 | 7.1 (9) | C22—O10—C23—C28 | 170.4 (5) |
O5—C9—C10—C11 | −179.9 (6) | C22—O10—C23—C24 | −9.4 (9) |
C14—C9—C10—C11 | −0.3 (9) | O10—C23—C24—C25 | 179.6 (6) |
C9—C10—C11—C12 | 0.3 (10) | C28—C23—C24—C25 | −0.2 (9) |
C9—C10—C11—Br1 | 179.4 (5) | C23—C24—C25—C26 | −0.3 (10) |
C10—C11—C12—C13 | −0.7 (10) | C23—C24—C25—Br3 | 179.8 (5) |
Br1—C11—C12—C13 | −179.7 (5) | C24—C25—C26—C27 | 0.3 (11) |
C10—C11—C12—Br2 | 177.0 (5) | Br3—C25—C26—C27 | −179.8 (5) |
Br1—C11—C12—Br2 | −2.0 (8) | C24—C25—C26—Br4 | −179.6 (5) |
C11—C12—C13—C14 | 1.1 (9) | Br3—C25—C26—Br4 | 0.3 (9) |
Br2—C12—C13—C14 | −176.8 (5) | C25—C26—C27—C28 | 0.3 (10) |
C1—O1—C14—C13 | −9.8 (8) | Br4—C26—C27—C28 | −179.9 (5) |
C1—O1—C14—C9 | 170.2 (5) | C15—O6—C28—C27 | 3.0 (9) |
C12—C13—C14—O1 | 178.9 (6) | C26—C27—C28—O6 | −179.4 (6) |
C12—C13—C14—C9 | −1.1 (9) | C26—C27—C28—C23 | −0.8 (9) |
C10—C9—C14—O1 | −179.3 (5) | C24—C23—C28—O6 | 179.5 (5) |
O5—C9—C14—C13 | −179.6 (5) | O10—C23—C28—C27 | −179.1 (5) |
C10—C9—C14—C13 | 0.7 (9) | C24—C23—C28—C27 | 0.7 (9) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O1 | 0.85 (8) | 2.40 (8) | 3.128 (8) | 143 (7) |
O1W—H1W1···O2 | 0.85 (8) | 2.18 (8) | 2.882 (8) | 140 (7) |
O1W—H1W2···O7 | 0.86 (6) | 2.16 (5) | 2.959 (8) | 156 (6) |
O1W—H1W2···O8 | 0.86 (6) | 2.34 (9) | 2.859 (9) | 119 (5) |
O1W—H1W3···O4 | 0.86 (8) | 2.06 (8) | 2.910 (9) | 168 (7) |
C22—H22A···Br5i | 0.97 | 2.86 | 3.676 (7) | 142 |
Symmetry code: (i) −x+1, −y+1, −z+1. |