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In the title compound, 2C14H18O5Br2·OH3+·Br3, the two 15-crown-5 macrocylic rings are linked by an oxonium cation via O—H...O 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806010932/at2019sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806010932/at2019Isup2.hkl
Contains datablock I

CCDC reference: 604959

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](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+·Br3Z = 2
Mr = 1110.96F(000) = 1080
Triclinic, P1Dx = 1.882 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.568 (3) ÅCell parameters from 957 reflections
b = 13.590 (3) Åθ = 1.6–25.0°
c = 13.829 (3) ŵ = 7.21 mm1
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 tube4087 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
Detector resolution: 83.66 pixels mm-1θmax = 25.0°, θmin = 1.6°
ω scanh = 1414
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
k = 1616
Tmin = 0.104, Tmax = 0.392l = 1616
18603 measured reflections
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H 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 parametersΔρmax = 0.92 e Å3
3 restraintsΔρmin = 0.85 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.27174 (9)1.19269 (7)0.30653 (7)0.0860 (3)
Br20.12568 (7)1.04647 (7)0.27397 (7)0.0825 (3)
Br30.10061 (8)0.74471 (9)0.31334 (10)0.1102 (4)
Br40.26009 (9)0.50512 (9)0.23460 (9)0.0980 (3)
Br50.83572 (9)0.03572 (9)0.38698 (12)0.1244 (5)
Br60.73873 (8)0.16895 (8)0.24797 (9)0.1019 (4)
Br70.64108 (11)0.30648 (11)0.10678 (12)0.1290 (5)
O10.5575 (4)0.8285 (3)0.0667 (3)0.0484 (11)
O20.6880 (4)0.6153 (3)0.0668 (3)0.0483 (11)
O30.9199 (4)0.6567 (4)0.0188 (3)0.0557 (12)
O40.8970 (4)0.8230 (4)0.1162 (4)0.0607 (12)
O50.6672 (4)0.9373 (3)0.0938 (3)0.0534 (11)
O60.5997 (4)0.5179 (3)0.3552 (3)0.0481 (11)
O70.8516 (4)0.4672 (4)0.2795 (3)0.0519 (11)
O80.8392 (4)0.6288 (4)0.3765 (4)0.0659 (13)
O90.6284 (4)0.8189 (4)0.3829 (4)0.0625 (13)
O100.4810 (4)0.6989 (3)0.4133 (3)0.0534 (11)
O1W0.7219 (5)0.6991 (5)0.2153 (5)0.0701 (14)
H1W10.682 (6)0.703 (6)0.176 (5)0.084*
H1W20.751 (7)0.637 (3)0.252 (6)0.084*
H1W30.776 (5)0.732 (6)0.195 (6)0.084*
C10.5038 (6)0.7538 (5)0.0635 (5)0.0489 (16)
H1A0.44430.79150.02540.059*
H1B0.46450.71940.13590.059*
C20.6057 (6)0.6710 (5)0.0055 (5)0.0526 (17)
H2A0.57490.61970.00260.063*
H2B0.64670.70650.06570.063*
C30.8056 (6)0.5595 (6)0.0064 (6)0.062 (2)
H3A0.79730.52950.04400.075*
H3B0.84300.49920.05530.075*
C40.8864 (6)0.6316 (6)0.0543 (6)0.065 (2)
H4A0.95810.59500.10510.078*
H4B0.84450.69810.09460.078*
C50.9940 (6)0.7289 (6)0.0311 (6)0.067 (2)
H5A0.95610.79310.07660.081*
H5B1.07230.69300.07570.081*
C61.0091 (6)0.7609 (7)0.0544 (7)0.072 (2)
H6A1.04250.69590.10190.087*
H6B1.06600.80360.02150.087*
C70.8648 (7)0.9351 (6)0.0673 (7)0.070 (2)
H7A0.88070.94350.00920.084*
H7B0.91310.97100.07580.084*
C80.7343 (6)0.9859 (6)0.1183 (6)0.0595 (19)
H8A0.71650.97290.19560.071*
H8B0.71301.06390.09000.071*
C90.5449 (6)0.9697 (5)0.1363 (5)0.0458 (15)
C100.4799 (6)1.0531 (5)0.1911 (5)0.0528 (17)
H10A0.51951.09240.20160.063*
C110.3563 (7)1.0774 (5)0.2300 (5)0.0578 (19)
C120.2959 (6)1.0211 (5)0.2163 (5)0.0557 (18)
C130.3593 (6)0.9369 (5)0.1606 (5)0.0497 (16)
H13A0.31840.89900.15000.060*
C140.4841 (6)0.9106 (5)0.1214 (5)0.0446 (15)
C150.6738 (6)0.4201 (5)0.3173 (6)0.0504 (16)
H15A0.68930.43280.24030.061*
H15B0.63370.36340.35310.061*
C160.7888 (6)0.3872 (5)0.3417 (6)0.0573 (18)
H16A0.77220.38100.41790.069*
H16B0.83840.31680.32420.069*
C170.9427 (7)0.4631 (7)0.3184 (7)0.072 (2)
H17A1.00010.49800.26040.087*
H17B0.98600.38750.34020.087*
C180.8932 (8)0.5173 (7)0.4116 (7)0.078 (2)
H18A0.83360.48480.46950.094*
H18B0.95780.50810.43830.094*
C190.7859 (7)0.6885 (7)0.4590 (6)0.076 (2)
H19A0.84720.68370.48780.091*
H19B0.72480.65810.51710.091*
C200.7298 (8)0.8044 (7)0.4147 (6)0.075 (2)
H20A0.70360.84670.46880.090*
H20B0.79010.83220.35290.090*
C210.5176 (7)0.8245 (6)0.4683 (6)0.067 (2)
H21A0.48540.89510.48720.080*
H21B0.53090.76900.53140.080*
C220.4311 (6)0.8069 (5)0.4322 (5)0.0584 (19)
H22A0.35270.81470.48720.070*
H22B0.42110.85950.36660.070*
C230.4229 (5)0.6619 (5)0.3749 (5)0.0439 (15)
C240.3083 (6)0.7148 (5)0.3654 (5)0.0534 (17)
H24A0.26450.78100.38650.064*
C250.2588 (6)0.6680 (6)0.3238 (6)0.0581 (19)
C260.3222 (6)0.5722 (6)0.2926 (6)0.0577 (18)
C270.4369 (6)0.5185 (5)0.3016 (5)0.0516 (17)
H27A0.47980.45270.27960.062*
C280.4876 (5)0.5621 (5)0.3431 (5)0.0438 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.1017 (7)0.0690 (5)0.0637 (5)0.0040 (5)0.0150 (5)0.0317 (4)
Br20.0519 (5)0.0811 (6)0.0797 (6)0.0016 (4)0.0066 (4)0.0118 (5)
Br30.0549 (5)0.1112 (8)0.1568 (10)0.0135 (5)0.0475 (6)0.0130 (7)
Br40.0909 (7)0.1187 (8)0.1225 (8)0.0494 (6)0.0523 (6)0.0261 (6)
Br50.0732 (7)0.0957 (8)0.1813 (12)0.0228 (6)0.0062 (7)0.0586 (8)
Br60.0617 (5)0.1163 (8)0.1480 (9)0.0449 (5)0.0214 (5)0.0963 (7)
Br70.1035 (8)0.1525 (11)0.1752 (12)0.0309 (7)0.0438 (8)0.0952 (10)
O10.046 (3)0.048 (3)0.057 (3)0.016 (2)0.012 (2)0.019 (2)
O20.051 (3)0.052 (3)0.046 (3)0.010 (2)0.019 (2)0.016 (2)
O30.052 (3)0.066 (3)0.047 (3)0.025 (2)0.006 (2)0.014 (2)
O40.053 (3)0.060 (3)0.071 (3)0.024 (2)0.012 (3)0.014 (3)
O50.052 (3)0.052 (3)0.060 (3)0.021 (2)0.009 (2)0.019 (2)
O60.041 (3)0.050 (3)0.057 (3)0.011 (2)0.014 (2)0.019 (2)
O70.044 (3)0.065 (3)0.047 (3)0.018 (2)0.015 (2)0.009 (2)
O80.072 (3)0.084 (4)0.053 (3)0.024 (3)0.025 (3)0.021 (3)
O90.074 (3)0.075 (3)0.048 (3)0.033 (3)0.011 (3)0.020 (2)
O100.058 (3)0.048 (3)0.057 (3)0.012 (2)0.016 (2)0.019 (2)
O1W0.076 (4)0.080 (4)0.066 (4)0.034 (3)0.029 (3)0.006 (3)
C10.049 (4)0.054 (4)0.050 (4)0.013 (3)0.023 (3)0.010 (3)
C20.059 (4)0.059 (4)0.049 (4)0.016 (3)0.021 (4)0.019 (3)
C30.055 (4)0.060 (4)0.080 (5)0.002 (4)0.024 (4)0.038 (4)
C40.051 (4)0.089 (6)0.052 (5)0.015 (4)0.005 (4)0.028 (4)
C50.049 (4)0.065 (5)0.068 (5)0.020 (4)0.002 (4)0.011 (4)
C60.042 (4)0.077 (5)0.101 (7)0.023 (4)0.015 (4)0.023 (5)
C70.063 (5)0.060 (5)0.090 (6)0.037 (4)0.011 (4)0.013 (4)
C80.064 (5)0.052 (4)0.071 (5)0.029 (4)0.013 (4)0.019 (4)
C90.048 (4)0.043 (4)0.041 (4)0.015 (3)0.009 (3)0.006 (3)
C100.059 (5)0.047 (4)0.048 (4)0.012 (3)0.017 (4)0.008 (3)
C110.073 (5)0.039 (4)0.047 (4)0.003 (4)0.016 (4)0.011 (3)
C120.052 (4)0.045 (4)0.048 (4)0.001 (3)0.014 (3)0.001 (3)
C130.047 (4)0.049 (4)0.048 (4)0.015 (3)0.016 (3)0.001 (3)
C140.053 (4)0.038 (4)0.037 (4)0.011 (3)0.015 (3)0.002 (3)
C150.050 (4)0.042 (4)0.059 (4)0.016 (3)0.016 (3)0.010 (3)
C160.048 (4)0.048 (4)0.061 (5)0.005 (3)0.016 (4)0.005 (4)
C170.052 (5)0.085 (6)0.090 (6)0.010 (4)0.035 (4)0.026 (5)
C180.084 (6)0.098 (7)0.076 (6)0.012 (5)0.057 (5)0.024 (5)
C190.077 (6)0.107 (7)0.066 (5)0.034 (5)0.033 (5)0.023 (5)
C200.092 (6)0.094 (7)0.068 (5)0.047 (5)0.023 (5)0.031 (5)
C210.087 (6)0.061 (5)0.055 (5)0.024 (4)0.009 (4)0.028 (4)
C220.071 (5)0.051 (4)0.043 (4)0.017 (4)0.002 (4)0.017 (3)
C230.038 (4)0.050 (4)0.039 (4)0.016 (3)0.005 (3)0.007 (3)
C240.045 (4)0.049 (4)0.048 (4)0.013 (3)0.001 (3)0.005 (3)
C250.037 (4)0.063 (5)0.064 (5)0.021 (4)0.012 (3)0.001 (4)
C260.049 (4)0.070 (5)0.062 (5)0.032 (4)0.020 (4)0.002 (4)
C270.047 (4)0.050 (4)0.058 (4)0.019 (3)0.009 (3)0.015 (3)
C280.038 (4)0.052 (4)0.040 (4)0.022 (3)0.003 (3)0.008 (3)
Geometric parameters (Å, º) top
Br1—C111.908 (6)C6—H6B0.9700
Br2—C121.898 (7)C7—C81.486 (9)
Br3—C251.900 (7)C7—H7A0.9700
Br4—C261.899 (7)C7—H7B0.9700
Br5—Br62.516 (2)C8—H8A0.9700
Br6—Br72.558 (2)C8—H8B0.9700
O1—C141.375 (7)C9—C101.378 (9)
O1—C11.435 (7)C9—C141.405 (8)
O2—C21.425 (7)C10—C111.370 (9)
O2—C31.430 (7)C10—H10A0.9300
O3—C41.411 (8)C11—C121.360 (10)
O3—C51.431 (8)C12—C131.393 (9)
O4—C71.417 (8)C13—C141.382 (9)
O4—C61.430 (8)C13—H13A0.9300
O5—C91.357 (7)C15—C161.483 (9)
O5—C81.436 (7)C15—H15A0.9700
O6—C281.359 (7)C15—H15B0.9700
O6—C151.429 (7)C16—H16A0.9700
O7—C171.422 (8)C16—H16B0.9700
O7—C161.430 (7)C17—C181.494 (10)
O8—C181.409 (9)C17—H17A0.9700
O8—C191.415 (8)C17—H17B0.9700
O9—C211.420 (8)C18—H18A0.9700
O9—C201.431 (8)C18—H18B0.9700
O10—C231.353 (7)C19—C201.487 (11)
O10—C221.429 (7)C19—H19A0.9700
O1W—H1W10.857 (10)C19—H19B0.9700
O1W—H1W20.855 (10)C20—H20A0.9700
O1W—H1W30.856 (10)C20—H20B0.9700
C1—C21.496 (9)C21—C221.481 (10)
C1—H1A0.9700C21—H21A0.9700
C1—H1B0.9700C21—H21B0.9700
C2—H2A0.9700C22—H22A0.9700
C2—H2B0.9700C22—H22B0.9700
C3—C41.496 (10)C23—C241.381 (9)
C3—H3A0.9700C23—C281.402 (8)
C3—H3B0.9700C24—C251.396 (9)
C4—H4A0.9700C24—H24A0.9300
C4—H4B0.9700C25—C261.351 (10)
C5—C61.484 (10)C26—C271.380 (9)
C5—H5A0.9700C27—C281.375 (8)
C5—H5B0.9700C27—H27A0.9300
C6—H6A0.9700
Br5—Br6—Br7179.21 (5)C13—C12—Br2116.1 (6)
C14—O1—C1118.1 (5)C14—C13—C12119.0 (6)
C2—O2—C3113.7 (5)C14—C13—H13A120.5
C4—O3—C5113.8 (5)C12—C13—H13A120.5
C7—O4—C6113.6 (6)O1—C14—C13124.9 (6)
C9—O5—C8117.0 (5)O1—C14—C9115.1 (5)
C28—O6—C15117.4 (5)C13—C14—C9120.0 (6)
C17—O7—C16113.9 (5)O6—C15—C16107.2 (5)
C18—O8—C19113.6 (6)O6—C15—H15A110.3
C21—O9—C20114.5 (5)C16—C15—H15A110.3
C23—O10—C22119.5 (5)O6—C15—H15B110.3
H1W1—O1W—H1W2119 (8)C16—C15—H15B110.3
H1W1—O1W—H1W3124 (8)H15A—C15—H15B108.5
H1W2—O1W—H1W3104 (8)O7—C16—C15109.0 (5)
O1—C1—C2105.8 (5)O7—C16—H16A109.9
O1—C1—H1A110.6C15—C16—H16A109.9
C2—C1—H1A110.6O7—C16—H16B109.9
O1—C1—H1B110.6C15—C16—H16B109.9
C2—C1—H1B110.6H16A—C16—H16B108.3
H1A—C1—H1B108.7O7—C17—C18113.0 (6)
O2—C2—C1108.3 (5)O7—C17—H17A109.0
O2—C2—H2A110.0C18—C17—H17A109.0
C1—C2—H2A110.0O7—C17—H17B109.0
O2—C2—H2B110.0C18—C17—H17B109.0
C1—C2—H2B110.0H17A—C17—H17B107.8
H2A—C2—H2B108.4O8—C18—C17108.4 (6)
O2—C3—C4112.9 (6)O8—C18—H18A110.0
O2—C3—H3A109.0C17—C18—H18A110.0
C4—C3—H3A109.0O8—C18—H18B110.0
O2—C3—H3B109.0C17—C18—H18B110.0
C4—C3—H3B109.0H18A—C18—H18B108.4
H3A—C3—H3B107.8O8—C19—C20109.6 (6)
O3—C4—C3109.4 (6)O8—C19—H19A109.8
O3—C4—H4A109.8C20—C19—H19A109.8
C3—C4—H4A109.8O8—C19—H19B109.8
O3—C4—H4B109.8C20—C19—H19B109.8
C3—C4—H4B109.8H19A—C19—H19B108.2
H4A—C4—H4B108.2O9—C20—C19112.8 (6)
O3—C5—C6108.7 (6)O9—C20—H20A109.0
O3—C5—H5A110.0C19—C20—H20A109.0
C6—C5—H5A110.0O9—C20—H20B109.0
O3—C5—H5B110.0C19—C20—H20B109.0
C6—C5—H5B110.0H20A—C20—H20B107.8
H5A—C5—H5B108.3O9—C21—C22108.4 (5)
O4—C6—C5112.0 (6)O9—C21—H21A110.0
O4—C6—H6A109.2C22—C21—H21A110.0
C5—C6—H6A109.2O9—C21—H21B110.0
O4—C6—H6B109.2C22—C21—H21B110.0
C5—C6—H6B109.2H21A—C21—H21B108.4
H6A—C6—H6B107.9O10—C22—C21106.5 (6)
O4—C7—C8109.6 (6)O10—C22—H22A110.4
O4—C7—H7A109.7C21—C22—H22A110.4
C8—C7—H7A109.7O10—C22—H22B110.4
O4—C7—H7B109.7C21—C22—H22B110.4
C8—C7—H7B109.7H22A—C22—H22B108.6
H7A—C7—H7B108.2O10—C23—C24125.0 (6)
O5—C8—C7107.2 (5)O10—C23—C28115.2 (5)
O5—C8—H8A110.3C24—C23—C28119.8 (6)
C7—C8—H8A110.3C23—C24—C25119.2 (6)
O5—C8—H8B110.3C23—C24—H24A120.4
C7—C8—H8B110.3C25—C24—H24A120.4
H8A—C8—H8B108.5C26—C25—C24120.6 (6)
O5—C9—C10125.2 (6)C26—C25—Br3122.2 (6)
O5—C9—C14115.0 (5)C24—C25—Br3117.2 (5)
C10—C9—C14119.8 (6)C25—C26—C27120.7 (6)
C11—C10—C9119.3 (6)C25—C26—Br4122.5 (5)
C11—C10—H10A120.4C27—C26—Br4116.8 (6)
C9—C10—H10A120.4C28—C27—C26120.0 (6)
C12—C11—C10121.7 (6)C28—C27—H27A120.0
C12—C11—Br1121.1 (6)C26—C27—H27A120.0
C10—C11—Br1117.2 (6)O6—C28—C27125.8 (6)
C11—C12—C13120.2 (6)O6—C28—C23114.6 (5)
C11—C12—Br2123.7 (5)C27—C28—C23119.6 (6)
O5—C9—C14—O10.4 (8)O10—C23—C28—O60.4 (8)
C9—O5—C8—C7177.8 (6)C23—O10—C22—C21177.3 (5)
O4—C7—C8—O565.1 (8)O9—C21—C22—O1063.6 (7)
C6—O4—C7—C8163.4 (6)C20—O9—C21—C22163.7 (6)
C7—O4—C6—C582.7 (8)C21—O9—C20—C1983.2 (8)
O3—C5—C6—O464.9 (8)O8—C19—C20—O966.6 (8)
C4—O3—C5—C6172.4 (6)C18—O8—C19—C20179.0 (6)
C5—O3—C4—C3177.8 (5)C19—O8—C18—C17178.4 (6)
O2—C3—C4—O371.2 (7)O7—C17—C18—O863.5 (9)
C2—O2—C3—C484.8 (7)C16—O7—C17—C1880.2 (8)
C3—O2—C2—C1161.4 (5)C17—O7—C16—C15162.0 (6)
O1—C1—C2—O262.5 (6)O6—C15—C16—O765.6 (7)
C14—O1—C1—C2176.5 (5)C28—O6—C15—C16178.7 (5)
C8—O5—C9—C14172.5 (5)C15—O6—C28—C23175.7 (5)
C8—O5—C9—C107.1 (9)C22—O10—C23—C28170.4 (5)
O5—C9—C10—C11179.9 (6)C22—O10—C23—C249.4 (9)
C14—C9—C10—C110.3 (9)O10—C23—C24—C25179.6 (6)
C9—C10—C11—C120.3 (10)C28—C23—C24—C250.2 (9)
C9—C10—C11—Br1179.4 (5)C23—C24—C25—C260.3 (10)
C10—C11—C12—C130.7 (10)C23—C24—C25—Br3179.8 (5)
Br1—C11—C12—C13179.7 (5)C24—C25—C26—C270.3 (11)
C10—C11—C12—Br2177.0 (5)Br3—C25—C26—C27179.8 (5)
Br1—C11—C12—Br22.0 (8)C24—C25—C26—Br4179.6 (5)
C11—C12—C13—C141.1 (9)Br3—C25—C26—Br40.3 (9)
Br2—C12—C13—C14176.8 (5)C25—C26—C27—C280.3 (10)
C1—O1—C14—C139.8 (8)Br4—C26—C27—C28179.9 (5)
C1—O1—C14—C9170.2 (5)C15—O6—C28—C273.0 (9)
C12—C13—C14—O1178.9 (6)C26—C27—C28—O6179.4 (6)
C12—C13—C14—C91.1 (9)C26—C27—C28—C230.8 (9)
C10—C9—C14—O1179.3 (5)C24—C23—C28—O6179.5 (5)
O5—C9—C14—C13179.6 (5)O10—C23—C28—C27179.1 (5)
C10—C9—C14—C130.7 (9)C24—C23—C28—C270.7 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W1···O10.85 (8)2.40 (8)3.128 (8)143 (7)
O1W—H1W1···O20.85 (8)2.18 (8)2.882 (8)140 (7)
O1W—H1W2···O70.86 (6)2.16 (5)2.959 (8)156 (6)
O1W—H1W2···O80.86 (6)2.34 (9)2.859 (9)119 (5)
O1W—H1W3···O40.86 (8)2.06 (8)2.910 (9)168 (7)
C22—H22A···Br5i0.972.863.676 (7)142
Symmetry code: (i) x+1, y+1, z+1.
 

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