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Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680500351X/is6045sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S160053680500351X/is6045Isup2.hkl |
CCDC reference: 269792
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(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
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.
C33H32Br4O4 | Dx = 1.646 Mg m−3 |
Mr = 812.23 | Melting point: 400.5 K |
Orthorhombic, Fdd2 | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: F 2 -2d | Cell parameters from 9698 reflections |
a = 25.342 (5) Å | θ = 4.0–68.1° |
b = 44.671 (5) Å | µ = 6.28 mm−1 |
c = 5.7889 (9) Å | T = 293 K |
V = 6553.3 (18) Å3 | Block, colorless |
Z = 8 | 0.25 × 0.05 × 0.05 mm |
F(000) = 3216 |
Bruker SMART6000 diffractometer | 2814 independent reflections |
Radiation source: rotating anode | 2559 reflections with I > 2σ(I) |
Montel 200 optics monochromator | Rint = 0.044 |
Detector resolution: 5.5 pixels mm-1 | θmax = 68.4°, θmin = 4.0° |
ω scans | h = −30→29 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | k = −53→53 |
Tmin = 0.620, Tmax = 0.730 | l = −6→6 |
16557 measured reflections |
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)] = 0.055 | H-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 reflections | Δρmax = 0.59 e Å−3 |
187 parameters | Δρmin = −0.47 e Å−3 |
1 restraint | Absolute structure: Flack (1983), with 1156 Friedel Pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.11 (4) |
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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.00316 (3) | 0.16962 (2) | 0.09172 (18) | 0.1113 (4) | |
Br2 | 0.39446 (4) | 0.422886 (15) | −0.11444 (16) | 0.1110 (4) | |
C1 | 0.2500 | 0.2500 | −0.5811 (12) | 0.0571 (14) | |
C2 | 0.2044 (2) | 0.25914 (11) | −0.4211 (9) | 0.0641 (11) | |
H2A | 0.1968 | 0.2431 | −0.3137 | 0.077* | |
H2B | 0.2143 | 0.2767 | −0.3328 | 0.077* | |
C3 | 0.1148 (2) | 0.27315 (13) | −0.4190 (13) | 0.0828 (16) | |
H3A | 0.0875 | 0.2812 | −0.5184 | 0.099* | |
H3B | 0.1249 | 0.2887 | −0.3110 | 0.099* | |
C4 | 0.0925 (2) | 0.24687 (13) | −0.2850 (12) | 0.0724 (13) | |
C5 | 0.0903 (3) | 0.21833 (14) | −0.3810 (14) | 0.0883 (17) | |
H5 | 0.1067 | 0.2147 | −0.5220 | 0.106* | |
C6 | 0.0642 (3) | 0.19520 (16) | −0.2701 (15) | 0.0909 (18) | |
H6 | 0.0628 | 0.1762 | −0.3360 | 0.109* | |
C7 | 0.0404 (2) | 0.20076 (14) | −0.0609 (12) | 0.0797 (16) | |
C8 | 0.0415 (2) | 0.22854 (16) | 0.0383 (13) | 0.0875 (17) | |
H8 | 0.0251 | 0.2319 | 0.1796 | 0.105* | |
C9 | 0.0676 (3) | 0.25183 (15) | −0.0753 (14) | 0.0896 (19) | |
H9 | 0.0683 | 0.2708 | −0.0096 | 0.107* | |
C10 | 0.2665 (2) | 0.27579 (10) | −0.7407 (9) | 0.0636 (11) | |
H10A | 0.2948 | 0.2693 | −0.8415 | 0.076* | |
H10B | 0.2368 | 0.2818 | −0.8360 | 0.076* | |
C11 | 0.3033 (3) | 0.32387 (12) | −0.7418 (12) | 0.0768 (14) | |
H11A | 0.2750 | 0.3324 | −0.8340 | 0.092* | |
H11B | 0.3303 | 0.3164 | −0.8458 | 0.092* | |
C12 | 0.3263 (2) | 0.34754 (10) | −0.5871 (10) | 0.0653 (12) | |
C13 | 0.3705 (2) | 0.36331 (12) | −0.6475 (12) | 0.0763 (14) | |
H13 | 0.3873 | 0.3587 | −0.7857 | 0.092* | |
C14 | 0.3909 (2) | 0.38558 (13) | −0.5128 (13) | 0.0814 (16) | |
H14 | 0.4206 | 0.3961 | −0.5606 | 0.098* | |
C15 | 0.3669 (2) | 0.39231 (11) | −0.3037 (10) | 0.0727 (14) | |
C16 | 0.3225 (2) | 0.37655 (12) | −0.2330 (12) | 0.0776 (14) | |
H16 | 0.3066 | 0.3809 | −0.0922 | 0.093* | |
C17 | 0.3023 (2) | 0.35438 (12) | −0.3736 (13) | 0.0763 (13) | |
H17 | 0.2724 | 0.3438 | −0.3270 | 0.092* | |
O1 | 0.15938 (14) | 0.26539 (9) | −0.5568 (8) | 0.0752 (9) | |
O2 | 0.28338 (14) | 0.30002 (7) | −0.6047 (7) | 0.0704 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0782 (4) | 0.1168 (6) | 0.1390 (8) | −0.0089 (3) | 0.0025 (4) | 0.0456 (6) |
Br2 | 0.1545 (8) | 0.0727 (4) | 0.1056 (6) | −0.0352 (4) | −0.0218 (5) | 0.0005 (4) |
C1 | 0.066 (4) | 0.049 (3) | 0.056 (4) | 0.003 (2) | 0.000 | 0.000 |
C2 | 0.073 (3) | 0.063 (2) | 0.056 (3) | −0.007 (2) | 0.008 (2) | −0.006 (2) |
C3 | 0.084 (3) | 0.069 (3) | 0.095 (4) | 0.010 (2) | 0.021 (3) | 0.008 (3) |
C4 | 0.061 (3) | 0.080 (3) | 0.076 (3) | 0.007 (2) | 0.007 (3) | −0.004 (3) |
C5 | 0.094 (4) | 0.077 (3) | 0.094 (4) | 0.001 (3) | 0.022 (4) | −0.008 (3) |
C6 | 0.088 (4) | 0.079 (4) | 0.105 (5) | −0.006 (3) | 0.013 (3) | −0.002 (4) |
C7 | 0.057 (3) | 0.096 (4) | 0.086 (4) | 0.000 (2) | 0.008 (3) | 0.015 (3) |
C8 | 0.076 (3) | 0.108 (5) | 0.078 (4) | 0.001 (3) | 0.018 (3) | 0.000 (3) |
C9 | 0.088 (4) | 0.098 (4) | 0.083 (5) | 0.001 (3) | 0.015 (3) | −0.014 (3) |
C10 | 0.079 (3) | 0.055 (2) | 0.057 (3) | −0.009 (2) | 0.001 (2) | 0.004 (2) |
C11 | 0.089 (3) | 0.063 (3) | 0.078 (4) | −0.019 (2) | −0.003 (3) | 0.010 (2) |
C12 | 0.073 (3) | 0.048 (2) | 0.075 (3) | −0.0001 (18) | 0.000 (2) | 0.010 (2) |
C13 | 0.073 (3) | 0.069 (3) | 0.087 (4) | −0.003 (2) | 0.007 (3) | 0.010 (3) |
C14 | 0.076 (3) | 0.072 (3) | 0.097 (4) | −0.020 (3) | 0.001 (3) | 0.009 (3) |
C15 | 0.088 (3) | 0.051 (2) | 0.079 (4) | −0.007 (2) | −0.014 (3) | 0.005 (2) |
C16 | 0.085 (3) | 0.064 (3) | 0.084 (4) | −0.009 (2) | 0.010 (3) | −0.002 (3) |
C17 | 0.069 (3) | 0.067 (3) | 0.093 (4) | −0.006 (2) | 0.009 (3) | 0.007 (3) |
O1 | 0.072 (2) | 0.078 (2) | 0.075 (2) | 0.0009 (17) | 0.0054 (18) | 0.0015 (18) |
O2 | 0.092 (2) | 0.0503 (15) | 0.069 (2) | −0.0151 (15) | 0.0041 (18) | 0.0010 (15) |
Br1—C7 | 1.899 (6) | C8—C9 | 1.397 (10) |
Br2—C15 | 1.885 (5) | C8—H8 | 0.93 |
C1—C10 | 1.534 (6) | C9—H9 | 0.93 |
C1—C10i | 1.534 (6) | C10—O2 | 1.405 (6) |
C1—C2i | 1.536 (6) | C10—H10A | 0.97 |
C1—C2 | 1.536 (6) | C10—H10B | 0.97 |
C2—O1 | 1.414 (7) | C11—O2 | 1.421 (6) |
C2—H2A | 0.97 | C11—C12 | 1.503 (8) |
C2—H2B | 0.97 | C11—H11A | 0.97 |
C3—O1 | 1.426 (7) | C11—H11B | 0.97 |
C3—C4 | 1.516 (8) | C12—C13 | 1.369 (8) |
C3—H3A | 0.97 | C12—C17 | 1.411 (9) |
C3—H3B | 0.97 | C13—C14 | 1.366 (9) |
C4—C9 | 1.386 (10) | C13—H13 | 0.93 |
C4—C5 | 1.391 (8) | C14—C15 | 1.388 (9) |
C5—C6 | 1.385 (10) | C14—H14 | 0.93 |
C5—H5 | 0.93 | C15—C16 | 1.388 (8) |
C6—C7 | 1.375 (10) | C16—C17 | 1.381 (9) |
C6—H6 | 0.93 | C16—H16 | 0.93 |
C7—C8 | 1.368 (10) | C17—H17 | 0.93 |
C10—C1—C10i | 106.0 (6) | C4—C9—H9 | 119.7 |
C10—C1—C2i | 111.0 (3) | C8—C9—H9 | 119.7 |
C10i—C1—C2i | 111.6 (3) | O2—C10—C1 | 108.9 (4) |
C10—C1—C2 | 111.6 (3) | O2—C10—H10A | 109.9 |
C10i—C1—C2 | 111.0 (3) | C1—C10—H10A | 109.9 |
C2i—C1—C2 | 105.8 (6) | O2—C10—H10B | 109.9 |
O1—C2—C1 | 108.9 (4) | C1—C10—H10B | 109.9 |
O1—C2—H2A | 109.9 | H10A—C10—H10B | 108.3 |
C1—C2—H2A | 109.9 | O2—C11—C12 | 109.4 (5) |
O1—C2—H2B | 109.9 | O2—C11—H11A | 109.8 |
C1—C2—H2B | 109.9 | C12—C11—H11A | 109.8 |
H2A—C2—H2B | 108.3 | O2—C11—H11B | 109.8 |
O1—C3—C4 | 113.2 (4) | C12—C11—H11B | 109.8 |
O1—C3—H3A | 108.9 | H11A—C11—H11B | 108.2 |
C4—C3—H3A | 108.9 | C13—C12—C17 | 117.7 (5) |
O1—C3—H3B | 108.9 | C13—C12—C11 | 121.8 (6) |
C4—C3—H3B | 108.9 | C17—C12—C11 | 120.5 (5) |
H3A—C3—H3B | 107.8 | C14—C13—C12 | 122.6 (6) |
C9—C4—C5 | 118.6 (6) | C14—C13—H13 | 118.7 |
C9—C4—C3 | 119.6 (5) | C12—C13—H13 | 118.7 |
C5—C4—C3 | 121.3 (6) | C13—C14—C15 | 119.3 (5) |
C6—C5—C4 | 121.1 (7) | C13—C14—H14 | 120.3 |
C6—C5—H5 | 119.4 | C15—C14—H14 | 120.3 |
C4—C5—H5 | 119.4 | C14—C15—C16 | 120.2 (5) |
C7—C6—C5 | 118.9 (7) | C14—C15—Br2 | 120.1 (4) |
C7—C6—H6 | 120.6 | C16—C15—Br2 | 119.8 (5) |
C5—C6—H6 | 120.6 | C17—C16—C15 | 119.4 (6) |
C8—C7—C6 | 121.7 (6) | C17—C16—H16 | 120.3 |
C8—C7—Br1 | 118.6 (5) | C15—C16—H16 | 120.3 |
C6—C7—Br1 | 119.7 (5) | C16—C17—C12 | 120.7 (5) |
C7—C8—C9 | 119.2 (6) | C16—C17—H17 | 119.6 |
C7—C8—H8 | 120.4 | C12—C17—H17 | 119.6 |
C9—C8—H8 | 120.4 | C2—O1—C3 | 112.2 (5) |
C4—C9—C8 | 120.6 (6) | C10—O2—C11 | 111.9 (4) |
C10—C1—C2—O1 | 64.2 (5) | C2—C1—C10—O2 | 60.5 (5) |
C10i—C1—C2—O1 | −53.7 (5) | O2—C11—C12—C13 | 143.4 (5) |
C2i—C1—C2—O1 | −174.9 (4) | O2—C11—C12—C17 | −37.1 (7) |
O1—C3—C4—C9 | 150.4 (6) | C17—C12—C13—C14 | −1.8 (9) |
O1—C3—C4—C5 | −37.9 (9) | C11—C12—C13—C14 | 177.7 (6) |
C9—C4—C5—C6 | −0.4 (10) | C12—C13—C14—C15 | 1.4 (9) |
C3—C4—C5—C6 | −172.0 (7) | C13—C14—C15—C16 | −0.1 (9) |
C4—C5—C6—C7 | −0.3 (11) | C13—C14—C15—Br2 | 179.8 (5) |
C5—C6—C7—C8 | 0.7 (10) | C14—C15—C16—C17 | −0.7 (9) |
C5—C6—C7—Br1 | 178.7 (5) | Br2—C15—C16—C17 | 179.4 (5) |
C6—C7—C8—C9 | −0.2 (9) | C15—C16—C17—C12 | 0.3 (9) |
Br1—C7—C8—C9 | −178.3 (6) | C13—C12—C17—C16 | 0.9 (8) |
C5—C4—C9—C8 | 0.9 (10) | C11—C12—C17—C16 | −178.6 (6) |
C3—C4—C9—C8 | 172.6 (7) | C1—C2—O1—C3 | 178.1 (4) |
C7—C8—C9—C4 | −0.6 (10) | C4—C3—O1—C2 | −70.5 (6) |
C10i—C1—C10—O2 | −178.5 (5) | C1—C10—O2—C11 | 175.2 (4) |
C2i—C1—C10—O2 | −57.2 (5) | C12—C11—O2—C10 | −173.7 (5) |
Symmetry code: (i) −x+1/2, −y+1/2, z. |
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