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The title compound {alternatively called tetra­kis­[(4-bromo­benz­yl­oxy)meth­yl]methane}, C33H32Br4O4, was crystallized from eth­yl acetate. The molecule has crystallographic twofold rotation symmetry. Key features of the structure include intra­molecular edge-to-face aromatic inter­actions, inter­molecular Br...π inter­actions and inter­molecular Br...O contacts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680500351X/is6045sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680500351X/is6045Isup2.hkl
Contains datablock I

CCDC reference: 269792

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.055
  • wR factor = 0.165
  • Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found




Alert level C PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293 PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9 PLAT431_ALERT_2_C Short Inter HL..A Contact Br2 .. O1 .. 3.30 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C33 H32 Br4 O4
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 68.36 From the CIF: _reflns_number_total 2814 Count of symmetry unique reflns 1658 Completeness (_total/calc) 169.72% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1156 Fraction of Friedel pairs measured 0.697 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 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, 2001); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

tetrakis[(4-bromobenzyloxy)methyl]methane top
Crystal data top
C33H32Br4O4Dx = 1.646 Mg m3
Mr = 812.23Melting point: 400.5 K
Orthorhombic, Fdd2Cu Kα radiation, λ = 1.54178 Å
Hall symbol: F 2 -2dCell parameters from 9698 reflections
a = 25.342 (5) Åθ = 4.0–68.1°
b = 44.671 (5) ŵ = 6.28 mm1
c = 5.7889 (9) ÅT = 293 K
V = 6553.3 (18) Å3Block, colorless
Z = 80.25 × 0.05 × 0.05 mm
F(000) = 3216
Data collection top
Bruker SMART6000
diffractometer
2814 independent reflections
Radiation source: rotating anode2559 reflections with I > 2σ(I)
Montel 200 optics monochromatorRint = 0.044
Detector resolution: 5.5 pixels mm-1θmax = 68.4°, θmin = 4.0°
ω scansh = 3029
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
k = 5353
Tmin = 0.620, Tmax = 0.730l = 66
16557 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.165 w = 1/[σ2(Fo2) + (0.1152P)2 + 3.049P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.035
2814 reflectionsΔρmax = 0.59 e Å3
187 parametersΔρmin = 0.47 e Å3
1 restraintAbsolute structure: Flack (1983), with 1156 Friedel Pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.11 (4)
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.

Refinement. The structure was solved by direct methods with SHELXS97. All non-Hydrogen atoms were refined by full-matrix least-squares with anisotropic displacement parameters. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.00316 (3)0.16962 (2)0.09172 (18)0.1113 (4)
Br20.39446 (4)0.422886 (15)0.11444 (16)0.1110 (4)
C10.25000.25000.5811 (12)0.0571 (14)
C20.2044 (2)0.25914 (11)0.4211 (9)0.0641 (11)
H2A0.19680.24310.31370.077*
H2B0.21430.27670.33280.077*
C30.1148 (2)0.27315 (13)0.4190 (13)0.0828 (16)
H3A0.08750.28120.51840.099*
H3B0.12490.28870.31100.099*
C40.0925 (2)0.24687 (13)0.2850 (12)0.0724 (13)
C50.0903 (3)0.21833 (14)0.3810 (14)0.0883 (17)
H50.10670.21470.52200.106*
C60.0642 (3)0.19520 (16)0.2701 (15)0.0909 (18)
H60.06280.17620.33600.109*
C70.0404 (2)0.20076 (14)0.0609 (12)0.0797 (16)
C80.0415 (2)0.22854 (16)0.0383 (13)0.0875 (17)
H80.02510.23190.17960.105*
C90.0676 (3)0.25183 (15)0.0753 (14)0.0896 (19)
H90.06830.27080.00960.107*
C100.2665 (2)0.27579 (10)0.7407 (9)0.0636 (11)
H10A0.29480.26930.84150.076*
H10B0.23680.28180.83600.076*
C110.3033 (3)0.32387 (12)0.7418 (12)0.0768 (14)
H11A0.27500.33240.83400.092*
H11B0.33030.31640.84580.092*
C120.3263 (2)0.34754 (10)0.5871 (10)0.0653 (12)
C130.3705 (2)0.36331 (12)0.6475 (12)0.0763 (14)
H130.38730.35870.78570.092*
C140.3909 (2)0.38558 (13)0.5128 (13)0.0814 (16)
H140.42060.39610.56060.098*
C150.3669 (2)0.39231 (11)0.3037 (10)0.0727 (14)
C160.3225 (2)0.37655 (12)0.2330 (12)0.0776 (14)
H160.30660.38090.09220.093*
C170.3023 (2)0.35438 (12)0.3736 (13)0.0763 (13)
H170.27240.34380.32700.092*
O10.15938 (14)0.26539 (9)0.5568 (8)0.0752 (9)
O20.28338 (14)0.30002 (7)0.6047 (7)0.0704 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0782 (4)0.1168 (6)0.1390 (8)0.0089 (3)0.0025 (4)0.0456 (6)
Br20.1545 (8)0.0727 (4)0.1056 (6)0.0352 (4)0.0218 (5)0.0005 (4)
C10.066 (4)0.049 (3)0.056 (4)0.003 (2)0.0000.000
C20.073 (3)0.063 (2)0.056 (3)0.007 (2)0.008 (2)0.006 (2)
C30.084 (3)0.069 (3)0.095 (4)0.010 (2)0.021 (3)0.008 (3)
C40.061 (3)0.080 (3)0.076 (3)0.007 (2)0.007 (3)0.004 (3)
C50.094 (4)0.077 (3)0.094 (4)0.001 (3)0.022 (4)0.008 (3)
C60.088 (4)0.079 (4)0.105 (5)0.006 (3)0.013 (3)0.002 (4)
C70.057 (3)0.096 (4)0.086 (4)0.000 (2)0.008 (3)0.015 (3)
C80.076 (3)0.108 (5)0.078 (4)0.001 (3)0.018 (3)0.000 (3)
C90.088 (4)0.098 (4)0.083 (5)0.001 (3)0.015 (3)0.014 (3)
C100.079 (3)0.055 (2)0.057 (3)0.009 (2)0.001 (2)0.004 (2)
C110.089 (3)0.063 (3)0.078 (4)0.019 (2)0.003 (3)0.010 (2)
C120.073 (3)0.048 (2)0.075 (3)0.0001 (18)0.000 (2)0.010 (2)
C130.073 (3)0.069 (3)0.087 (4)0.003 (2)0.007 (3)0.010 (3)
C140.076 (3)0.072 (3)0.097 (4)0.020 (3)0.001 (3)0.009 (3)
C150.088 (3)0.051 (2)0.079 (4)0.007 (2)0.014 (3)0.005 (2)
C160.085 (3)0.064 (3)0.084 (4)0.009 (2)0.010 (3)0.002 (3)
C170.069 (3)0.067 (3)0.093 (4)0.006 (2)0.009 (3)0.007 (3)
O10.072 (2)0.078 (2)0.075 (2)0.0009 (17)0.0054 (18)0.0015 (18)
O20.092 (2)0.0503 (15)0.069 (2)0.0151 (15)0.0041 (18)0.0010 (15)
Geometric parameters (Å, º) top
Br1—C71.899 (6)C8—C91.397 (10)
Br2—C151.885 (5)C8—H80.93
C1—C101.534 (6)C9—H90.93
C1—C10i1.534 (6)C10—O21.405 (6)
C1—C2i1.536 (6)C10—H10A0.97
C1—C21.536 (6)C10—H10B0.97
C2—O11.414 (7)C11—O21.421 (6)
C2—H2A0.97C11—C121.503 (8)
C2—H2B0.97C11—H11A0.97
C3—O11.426 (7)C11—H11B0.97
C3—C41.516 (8)C12—C131.369 (8)
C3—H3A0.97C12—C171.411 (9)
C3—H3B0.97C13—C141.366 (9)
C4—C91.386 (10)C13—H130.93
C4—C51.391 (8)C14—C151.388 (9)
C5—C61.385 (10)C14—H140.93
C5—H50.93C15—C161.388 (8)
C6—C71.375 (10)C16—C171.381 (9)
C6—H60.93C16—H160.93
C7—C81.368 (10)C17—H170.93
C10—C1—C10i106.0 (6)C4—C9—H9119.7
C10—C1—C2i111.0 (3)C8—C9—H9119.7
C10i—C1—C2i111.6 (3)O2—C10—C1108.9 (4)
C10—C1—C2111.6 (3)O2—C10—H10A109.9
C10i—C1—C2111.0 (3)C1—C10—H10A109.9
C2i—C1—C2105.8 (6)O2—C10—H10B109.9
O1—C2—C1108.9 (4)C1—C10—H10B109.9
O1—C2—H2A109.9H10A—C10—H10B108.3
C1—C2—H2A109.9O2—C11—C12109.4 (5)
O1—C2—H2B109.9O2—C11—H11A109.8
C1—C2—H2B109.9C12—C11—H11A109.8
H2A—C2—H2B108.3O2—C11—H11B109.8
O1—C3—C4113.2 (4)C12—C11—H11B109.8
O1—C3—H3A108.9H11A—C11—H11B108.2
C4—C3—H3A108.9C13—C12—C17117.7 (5)
O1—C3—H3B108.9C13—C12—C11121.8 (6)
C4—C3—H3B108.9C17—C12—C11120.5 (5)
H3A—C3—H3B107.8C14—C13—C12122.6 (6)
C9—C4—C5118.6 (6)C14—C13—H13118.7
C9—C4—C3119.6 (5)C12—C13—H13118.7
C5—C4—C3121.3 (6)C13—C14—C15119.3 (5)
C6—C5—C4121.1 (7)C13—C14—H14120.3
C6—C5—H5119.4C15—C14—H14120.3
C4—C5—H5119.4C14—C15—C16120.2 (5)
C7—C6—C5118.9 (7)C14—C15—Br2120.1 (4)
C7—C6—H6120.6C16—C15—Br2119.8 (5)
C5—C6—H6120.6C17—C16—C15119.4 (6)
C8—C7—C6121.7 (6)C17—C16—H16120.3
C8—C7—Br1118.6 (5)C15—C16—H16120.3
C6—C7—Br1119.7 (5)C16—C17—C12120.7 (5)
C7—C8—C9119.2 (6)C16—C17—H17119.6
C7—C8—H8120.4C12—C17—H17119.6
C9—C8—H8120.4C2—O1—C3112.2 (5)
C4—C9—C8120.6 (6)C10—O2—C11111.9 (4)
C10—C1—C2—O164.2 (5)C2—C1—C10—O260.5 (5)
C10i—C1—C2—O153.7 (5)O2—C11—C12—C13143.4 (5)
C2i—C1—C2—O1174.9 (4)O2—C11—C12—C1737.1 (7)
O1—C3—C4—C9150.4 (6)C17—C12—C13—C141.8 (9)
O1—C3—C4—C537.9 (9)C11—C12—C13—C14177.7 (6)
C9—C4—C5—C60.4 (10)C12—C13—C14—C151.4 (9)
C3—C4—C5—C6172.0 (7)C13—C14—C15—C160.1 (9)
C4—C5—C6—C70.3 (11)C13—C14—C15—Br2179.8 (5)
C5—C6—C7—C80.7 (10)C14—C15—C16—C170.7 (9)
C5—C6—C7—Br1178.7 (5)Br2—C15—C16—C17179.4 (5)
C6—C7—C8—C90.2 (9)C15—C16—C17—C120.3 (9)
Br1—C7—C8—C9178.3 (6)C13—C12—C17—C160.9 (8)
C5—C4—C9—C80.9 (10)C11—C12—C17—C16178.6 (6)
C3—C4—C9—C8172.6 (7)C1—C2—O1—C3178.1 (4)
C7—C8—C9—C40.6 (10)C4—C3—O1—C270.5 (6)
C10i—C1—C10—O2178.5 (5)C1—C10—O2—C11175.2 (4)
C2i—C1—C10—O257.2 (5)C12—C11—O2—C10173.7 (5)
Symmetry code: (i) x+1/2, y+1/2, z.
 

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