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Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536814004383/xu5768sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536814004383/xu5768Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536814004383/xu5768Isup3.cml |
CCDC reference: 988768
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.026
- wR factor = 0.057
- Data-to-parameter ratio = 22.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) Range 3.8 Ratio PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors of C1A Check PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors of C2A Check PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 3.5 Note PLAT410_ALERT_2_C Short Intra H...H Contact H8B .. H28A .. 1.94 Ang. PLAT410_ALERT_2_C Short Intra H...H Contact H9B .. H28B .. 1.96 Ang.
Alert level G PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF Please Do ! PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 3 Note PLAT910_ALERT_3_G Missing # of FCF Reflections Below Th(Min) ..... 3 Why ?
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 6 ALERT level C = Check. Ensure it is not caused by an omission or oversight 3 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 3 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
The synthesis of the title compound was carried out in a slightly modified literature procedure (Roelens et al. 2009). 1,3,5-Tris(phthalimidomethyl)-2,4,6-trimethylbenzene (1.00 g, 1.67 mmol) was dissolved in 1,2-dibromoethane (20 ml) and bromine (0.28 ml, 5.50 mmol) was added. The reaction mixture was stirred for overall 48 h under reflux and irradiation with a halogen bulb (500 W); after 24 h an additional amount of bromine (0.28 ml, 5.50 mmol) was added. The reaction mixture was cooled and washed with saturated aqueous solutions of sodium metabisulfite (2 x 20 ml), sodium bicarbonate (20 ml), and distilled water (20 ml). The organic phase was dried over sodium sulfate and the solvent removed by distillation. The residue was purified by column chromatography (SiO2, CH2Cl2, Rf= 0.32) and the product obtained as an off-white solid. Analysis data: m.p. > 467 K; 1H NMR (400 MHz, CDCl3) δ 7.87–7.77 (m, 6H, aryl), 7.75–7.67 (m, 6H, aryl), 5.10 (s, 12H CH2); 13C NMR (100 MHz, CDCl3) δ 29.26, 36.40, 123.48, 132.03, 134.18, 134.87, 140.32, 168.28; EI—MS (70 eV) m/z: 595, 675, 754.
H atoms were positioned geometrically and allowed to ride on their respective parent atoms, with C—H = 0.95 Å and Uiso(H) = 1.2 Ueq(C) for aryl, C—H = 0.99 Å and Uiso(H) = 1.2 Ueq(C) for methylene and C—H = 0.98 Å and Uiso(H) = 1.5 Ueq(C) for methyl.
Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
C36H24Br3N3O6·C7H8 | F(000) = 1856 |
Mr = 926.45 | Dx = 1.598 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 9504 reflections |
a = 9.2879 (2) Å | θ = 2.6–30.1° |
b = 39.2730 (11) Å | µ = 3.20 mm−1 |
c = 10.5592 (3) Å | T = 100 K |
V = 3851.61 (17) Å3 | Irregular, colourless |
Z = 4 | 0.50 × 0.42 × 0.34 mm |
Bruker APEXII CCD area-detector diffractometer | 10997 independent reflections |
Radiation source: fine-focus sealed tube | 10267 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
phi and ω scans | θmax = 29.8°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −12→12 |
Tmin = 0.298, Tmax = 0.410 | k = −54→54 |
59694 measured reflections | l = −14→14 |
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)] = 0.026 | H-atom parameters constrained |
wR(F2) = 0.057 | w = 1/[σ2(Fo2) + (0.0167P)2 + 1.9141P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
10997 reflections | Δρmax = 0.41 e Å−3 |
482 parameters | Δρmin = −0.43 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 5205 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.015 (4) |
C36H24Br3N3O6·C7H8 | V = 3851.61 (17) Å3 |
Mr = 926.45 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 9.2879 (2) Å | µ = 3.20 mm−1 |
b = 39.2730 (11) Å | T = 100 K |
c = 10.5592 (3) Å | 0.50 × 0.42 × 0.34 mm |
Bruker APEXII CCD area-detector diffractometer | 10997 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 10267 reflections with I > 2σ(I) |
Tmin = 0.298, Tmax = 0.410 | Rint = 0.029 |
59694 measured reflections |
R[F2 > 2σ(F2)] = 0.026 | H-atom parameters constrained |
wR(F2) = 0.057 | Δρmax = 0.41 e Å−3 |
S = 1.06 | Δρmin = −0.43 e Å−3 |
10997 reflections | Absolute structure: Flack (1983), 5205 Friedel pairs |
482 parameters | Absolute structure parameter: 0.015 (4) |
1 restraint |
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. 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 | 0.87579 (2) | 0.101954 (5) | −0.01024 (2) | 0.02056 (5) | |
Br2 | 1.31949 (2) | 0.203008 (5) | 0.23399 (2) | 0.01976 (4) | |
Br3 | 0.62645 (2) | 0.184625 (6) | 0.55424 (2) | 0.02518 (5) | |
O1 | 0.62966 (17) | 0.18819 (4) | 0.09052 (18) | 0.0237 (4) | |
O2 | 0.50556 (16) | 0.07721 (3) | 0.15611 (16) | 0.0186 (3) | |
O3 | 1.16142 (18) | 0.04624 (4) | 0.10085 (18) | 0.0278 (4) | |
O4 | 1.3171 (2) | 0.10168 (4) | 0.45440 (17) | 0.0289 (4) | |
O5 | 1.10398 (16) | 0.16994 (4) | 0.62809 (16) | 0.0188 (3) | |
O6 | 0.81813 (16) | 0.26402 (4) | 0.58804 (16) | 0.0197 (3) | |
N1 | 0.58624 (17) | 0.13273 (4) | 0.15120 (17) | 0.0138 (3) | |
N2 | 1.20917 (17) | 0.08138 (4) | 0.27224 (17) | 0.0144 (3) | |
N3 | 0.97292 (17) | 0.21791 (4) | 0.57551 (16) | 0.0123 (3) | |
C1 | 0.79776 (19) | 0.14557 (5) | 0.29093 (19) | 0.0118 (4) | |
C2 | 0.90990 (19) | 0.12503 (4) | 0.2461 (2) | 0.0120 (3) | |
C3 | 1.0543 (2) | 0.13449 (5) | 0.26749 (18) | 0.0117 (4) | |
C4 | 1.0854 (2) | 0.16428 (5) | 0.33462 (19) | 0.0113 (4) | |
C5 | 0.9733 (2) | 0.18575 (4) | 0.37434 (19) | 0.0109 (4) | |
C6 | 0.8299 (2) | 0.17643 (5) | 0.35213 (19) | 0.0120 (4) | |
C7 | 0.8773 (2) | 0.09313 (5) | 0.1739 (2) | 0.0146 (4) | |
H7A | 0.7823 | 0.0842 | 0.2003 | 0.017* | |
H7B | 0.9508 | 0.0757 | 0.1935 | 0.017* | |
C8 | 1.2373 (2) | 0.17347 (5) | 0.3659 (2) | 0.0132 (4) | |
H8A | 1.2957 | 0.1525 | 0.3733 | 0.016* | |
H8B | 1.2401 | 0.1854 | 0.4484 | 0.016* | |
C9 | 0.7111 (2) | 0.19981 (5) | 0.3924 (2) | 0.0164 (4) | |
H9A | 0.6356 | 0.2003 | 0.3263 | 0.020* | |
H9B | 0.7494 | 0.2232 | 0.4021 | 0.020* | |
C10 | 0.6420 (2) | 0.13404 (5) | 0.2795 (2) | 0.0144 (4) | |
H10A | 0.6332 | 0.1111 | 0.3176 | 0.017* | |
H10B | 0.5810 | 0.1497 | 0.3297 | 0.017* | |
C11 | 0.5808 (2) | 0.16045 (5) | 0.0676 (2) | 0.0181 (4) | |
C12 | 0.5030 (2) | 0.14809 (6) | −0.0454 (2) | 0.0193 (4) | |
C13 | 0.4667 (2) | 0.16503 (7) | −0.1558 (2) | 0.0302 (6) | |
H13 | 0.4953 | 0.1879 | −0.1703 | 0.036* | |
C14 | 0.3862 (2) | 0.14693 (9) | −0.2448 (3) | 0.0396 (7) | |
H14 | 0.3603 | 0.1577 | −0.3221 | 0.048* | |
C15 | 0.3432 (3) | 0.11369 (9) | −0.2229 (3) | 0.0413 (8) | |
H15 | 0.2870 | 0.1022 | −0.2848 | 0.050* | |
C16 | 0.3809 (2) | 0.09660 (8) | −0.1111 (3) | 0.0302 (6) | |
H16 | 0.3523 | 0.0738 | −0.0957 | 0.036* | |
C17 | 0.4624 (2) | 0.11481 (6) | −0.0243 (2) | 0.0196 (4) | |
C18 | 0.5164 (2) | 0.10438 (5) | 0.1015 (2) | 0.0151 (4) | |
C19 | 1.1748 (2) | 0.11348 (5) | 0.20873 (19) | 0.0132 (4) | |
H19A | 1.1484 | 0.1084 | 0.1199 | 0.016* | |
H19B | 1.2630 | 0.1276 | 0.2067 | 0.016* | |
C20 | 1.2076 (2) | 0.05012 (5) | 0.2068 (2) | 0.0194 (5) | |
C21 | 1.2715 (2) | 0.02478 (5) | 0.2940 (2) | 0.0220 (5) | |
C22 | 1.2896 (2) | −0.01012 (6) | 0.2806 (3) | 0.0313 (6) | |
H22 | 1.2603 | −0.0217 | 0.2059 | 0.038* | |
C23 | 1.3520 (3) | −0.02728 (6) | 0.3804 (4) | 0.0386 (7) | |
H23 | 1.3643 | −0.0512 | 0.3749 | 0.046* | |
C24 | 1.3972 (3) | −0.01038 (6) | 0.4888 (4) | 0.0392 (7) | |
H24 | 1.4407 | −0.0229 | 0.5555 | 0.047* | |
C25 | 1.3799 (3) | 0.02466 (6) | 0.5013 (3) | 0.0327 (6) | |
H25 | 1.4109 | 0.0364 | 0.5751 | 0.039* | |
C26 | 1.3160 (2) | 0.04157 (5) | 0.4020 (2) | 0.0223 (5) | |
C27 | 1.2844 (2) | 0.07837 (5) | 0.3867 (2) | 0.0191 (4) | |
C28 | 1.0073 (2) | 0.21895 (5) | 0.44127 (19) | 0.0124 (4) | |
H28A | 1.1110 | 0.2241 | 0.4309 | 0.015* | |
H28B | 0.9520 | 0.2376 | 0.4009 | 0.015* | |
C29 | 1.0301 (2) | 0.19385 (5) | 0.6595 (2) | 0.0148 (4) | |
C30 | 0.9806 (2) | 0.20383 (5) | 0.7871 (2) | 0.0170 (4) | |
C31 | 1.0109 (2) | 0.18917 (6) | 0.9036 (2) | 0.0217 (5) | |
H31 | 1.0716 | 0.1698 | 0.9110 | 0.026* | |
C32 | 0.9476 (3) | 0.20435 (6) | 1.0092 (2) | 0.0292 (5) | |
H32 | 0.9658 | 0.1953 | 1.0911 | 0.035* | |
C33 | 0.8587 (3) | 0.23229 (6) | 0.9963 (3) | 0.0299 (5) | |
H33 | 0.8164 | 0.2419 | 1.0701 | 0.036* | |
C34 | 0.8289 (3) | 0.24692 (6) | 0.8796 (2) | 0.0232 (5) | |
H34 | 0.7676 | 0.2662 | 0.8721 | 0.028* | |
C35 | 0.8927 (2) | 0.23217 (5) | 0.7747 (2) | 0.0172 (4) | |
C36 | 0.8850 (2) | 0.24137 (5) | 0.6388 (2) | 0.0155 (4) | |
C1A | 0.8364 (2) | 0.03354 (5) | 0.44059 (17) | 0.0507 (9) | |
C2A | 0.7319 (2) | 0.05829 (5) | 0.4604 (2) | 0.0498 (8) | |
H2A | 0.6435 | 0.0573 | 0.4151 | 0.060* | |
C3A | 0.7565 (3) | 0.08446 (5) | 0.5463 (2) | 0.0810 (14) | |
H3A | 0.6850 | 0.1014 | 0.5598 | 0.097* | |
C4A | 0.8858 (4) | 0.08588 (6) | 0.6124 (2) | 0.0887 (18) | |
H4A | 0.9026 | 0.1038 | 0.6712 | 0.106* | |
C5A | 0.9904 (3) | 0.06113 (8) | 0.5927 (2) | 0.0813 (15) | |
H5A | 1.0787 | 0.0621 | 0.6379 | 0.098* | |
C6A | 0.96570 (19) | 0.03496 (7) | 0.5067 (2) | 0.0693 (12) | |
H6A | 1.0372 | 0.0180 | 0.4932 | 0.083* | |
C7A | 0.8255 (4) | 0.00470 (6) | 0.3449 (2) | 0.0941 (18) | |
H7A1 | 0.7240 | −0.0012 | 0.3319 | 0.141* | |
H7A2 | 0.8776 | −0.0152 | 0.3767 | 0.141* | |
H7A3 | 0.8677 | 0.0120 | 0.2642 | 0.141* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.02090 (10) | 0.02545 (10) | 0.01532 (10) | −0.00046 (8) | −0.00065 (9) | −0.00518 (9) |
Br2 | 0.01633 (8) | 0.02241 (9) | 0.02055 (10) | −0.00556 (8) | 0.00482 (9) | 0.00259 (9) |
Br3 | 0.01890 (10) | 0.03088 (11) | 0.02576 (12) | −0.00392 (8) | 0.01001 (10) | −0.01086 (10) |
O1 | 0.0196 (7) | 0.0195 (7) | 0.0320 (10) | 0.0003 (6) | 0.0050 (7) | 0.0052 (7) |
O2 | 0.0196 (7) | 0.0134 (6) | 0.0228 (8) | −0.0023 (5) | 0.0005 (6) | −0.0051 (6) |
O3 | 0.0283 (9) | 0.0211 (8) | 0.0340 (10) | 0.0060 (6) | −0.0097 (7) | −0.0118 (7) |
O4 | 0.0437 (11) | 0.0207 (8) | 0.0223 (9) | 0.0049 (7) | −0.0119 (7) | −0.0006 (7) |
O5 | 0.0186 (7) | 0.0170 (7) | 0.0208 (8) | 0.0065 (5) | 0.0003 (6) | 0.0032 (6) |
O6 | 0.0195 (7) | 0.0140 (7) | 0.0255 (9) | 0.0049 (5) | −0.0014 (6) | −0.0022 (6) |
N1 | 0.0108 (8) | 0.0153 (7) | 0.0152 (9) | −0.0007 (6) | −0.0010 (6) | −0.0015 (6) |
N2 | 0.0132 (8) | 0.0125 (7) | 0.0176 (9) | 0.0024 (6) | 0.0003 (6) | −0.0013 (6) |
N3 | 0.0141 (7) | 0.0108 (7) | 0.0120 (9) | 0.0015 (6) | −0.0002 (6) | −0.0023 (6) |
C1 | 0.0089 (8) | 0.0136 (8) | 0.0130 (10) | −0.0002 (6) | −0.0009 (7) | 0.0008 (7) |
C2 | 0.0125 (8) | 0.0120 (8) | 0.0114 (9) | −0.0012 (6) | 0.0001 (7) | 0.0007 (7) |
C3 | 0.0121 (8) | 0.0107 (8) | 0.0122 (9) | 0.0024 (6) | −0.0002 (7) | 0.0019 (7) |
C4 | 0.0099 (8) | 0.0124 (8) | 0.0116 (10) | 0.0004 (6) | −0.0004 (7) | 0.0025 (7) |
C5 | 0.0103 (8) | 0.0105 (8) | 0.0119 (10) | −0.0008 (6) | −0.0003 (7) | 0.0011 (7) |
C6 | 0.0105 (8) | 0.0134 (8) | 0.0121 (9) | 0.0014 (6) | −0.0008 (7) | −0.0012 (7) |
C7 | 0.0154 (9) | 0.0129 (8) | 0.0153 (10) | −0.0006 (7) | −0.0003 (8) | −0.0021 (7) |
C8 | 0.0110 (8) | 0.0133 (8) | 0.0153 (10) | −0.0033 (7) | 0.0005 (7) | 0.0013 (7) |
C9 | 0.0114 (9) | 0.0165 (9) | 0.0211 (11) | 0.0014 (7) | −0.0001 (8) | −0.0059 (8) |
C10 | 0.0100 (8) | 0.0182 (9) | 0.0148 (10) | −0.0022 (7) | −0.0003 (7) | −0.0027 (7) |
C11 | 0.0116 (8) | 0.0216 (9) | 0.0211 (11) | 0.0037 (7) | 0.0046 (8) | 0.0024 (9) |
C12 | 0.0113 (9) | 0.0303 (11) | 0.0163 (11) | 0.0051 (8) | 0.0026 (7) | 0.0028 (8) |
C13 | 0.0156 (10) | 0.0522 (15) | 0.0228 (13) | 0.0093 (10) | 0.0039 (9) | 0.0130 (11) |
C14 | 0.0174 (11) | 0.082 (2) | 0.0198 (13) | 0.0076 (12) | −0.0012 (10) | 0.0112 (13) |
C15 | 0.0153 (11) | 0.089 (2) | 0.0190 (13) | −0.0030 (12) | −0.0040 (9) | −0.0087 (14) |
C16 | 0.0153 (11) | 0.0512 (15) | 0.0242 (13) | −0.0040 (10) | −0.0011 (9) | −0.0113 (11) |
C17 | 0.0124 (9) | 0.0274 (10) | 0.0189 (11) | 0.0051 (7) | −0.0001 (8) | −0.0066 (9) |
C18 | 0.0091 (8) | 0.0188 (9) | 0.0176 (10) | 0.0018 (7) | 0.0017 (7) | −0.0067 (8) |
C19 | 0.0122 (8) | 0.0132 (8) | 0.0142 (11) | 0.0009 (7) | 0.0015 (7) | −0.0003 (7) |
C20 | 0.0141 (9) | 0.0149 (9) | 0.0291 (14) | 0.0011 (7) | 0.0005 (8) | −0.0034 (8) |
C21 | 0.0149 (9) | 0.0156 (9) | 0.0354 (14) | 0.0010 (7) | 0.0021 (9) | 0.0019 (9) |
C22 | 0.0228 (11) | 0.0169 (10) | 0.0542 (18) | 0.0028 (8) | −0.0008 (11) | 0.0001 (10) |
C23 | 0.0284 (13) | 0.0144 (10) | 0.073 (2) | 0.0023 (9) | −0.0004 (13) | 0.0116 (12) |
C24 | 0.0355 (14) | 0.0264 (12) | 0.0558 (19) | 0.0055 (10) | −0.0055 (14) | 0.0185 (14) |
C25 | 0.0336 (13) | 0.0279 (11) | 0.0366 (15) | 0.0050 (10) | 0.0006 (12) | 0.0129 (11) |
C26 | 0.0188 (10) | 0.0174 (9) | 0.0306 (13) | 0.0021 (8) | 0.0019 (9) | 0.0067 (9) |
C27 | 0.0195 (10) | 0.0190 (9) | 0.0189 (11) | 0.0036 (8) | −0.0002 (8) | 0.0018 (8) |
C28 | 0.0123 (9) | 0.0120 (8) | 0.0128 (9) | −0.0003 (7) | −0.0016 (7) | 0.0002 (7) |
C29 | 0.0119 (9) | 0.0169 (9) | 0.0157 (10) | −0.0012 (7) | −0.0012 (8) | 0.0018 (8) |
C30 | 0.0155 (9) | 0.0205 (10) | 0.0150 (10) | −0.0058 (8) | −0.0004 (8) | −0.0003 (8) |
C31 | 0.0207 (11) | 0.0261 (11) | 0.0184 (11) | −0.0059 (8) | −0.0015 (9) | 0.0039 (9) |
C32 | 0.0363 (14) | 0.0348 (13) | 0.0164 (12) | −0.0132 (10) | 0.0043 (10) | −0.0003 (9) |
C33 | 0.0392 (14) | 0.0307 (11) | 0.0197 (12) | −0.0137 (10) | 0.0120 (11) | −0.0092 (11) |
C34 | 0.0257 (11) | 0.0197 (10) | 0.0241 (13) | −0.0056 (8) | 0.0079 (10) | −0.0081 (9) |
C35 | 0.0161 (9) | 0.0172 (9) | 0.0182 (11) | −0.0049 (7) | 0.0005 (8) | −0.0051 (8) |
C36 | 0.0127 (9) | 0.0134 (8) | 0.0202 (11) | −0.0013 (7) | −0.0001 (8) | −0.0048 (8) |
C1A | 0.055 (2) | 0.059 (2) | 0.0382 (19) | −0.0185 (16) | 0.0039 (15) | 0.0224 (16) |
C2A | 0.057 (2) | 0.0499 (18) | 0.042 (2) | −0.0087 (15) | −0.0076 (15) | 0.0249 (15) |
C3A | 0.150 (5) | 0.045 (2) | 0.048 (2) | 0.016 (2) | 0.005 (3) | 0.0289 (19) |
C4A | 0.180 (6) | 0.055 (2) | 0.032 (2) | −0.052 (3) | −0.004 (3) | 0.0074 (18) |
C5A | 0.077 (3) | 0.096 (3) | 0.071 (3) | −0.053 (3) | −0.007 (2) | 0.020 (3) |
C6A | 0.0417 (19) | 0.109 (3) | 0.057 (3) | −0.019 (2) | 0.0108 (17) | 0.028 (2) |
C7A | 0.171 (6) | 0.058 (2) | 0.053 (3) | −0.017 (3) | 0.016 (3) | 0.011 (2) |
Br1—C7 | 1.975 (2) | C16—C17 | 1.387 (3) |
Br2—C8 | 1.967 (2) | C16—H16 | 0.9500 |
Br3—C9 | 1.974 (2) | C17—C18 | 1.478 (3) |
O1—C11 | 1.205 (3) | C19—H19A | 0.9900 |
O2—C18 | 1.217 (3) | C19—H19B | 0.9900 |
O3—C20 | 1.208 (3) | C20—C21 | 1.480 (3) |
O4—C27 | 1.201 (3) | C21—C26 | 1.380 (3) |
O5—C29 | 1.209 (2) | C21—C22 | 1.388 (3) |
O6—C36 | 1.210 (2) | C22—C23 | 1.379 (4) |
N1—C18 | 1.391 (2) | C22—H22 | 0.9500 |
N1—C11 | 1.403 (3) | C23—C24 | 1.388 (5) |
N1—C10 | 1.451 (3) | C23—H23 | 0.9500 |
N2—C27 | 1.401 (3) | C24—C25 | 1.392 (4) |
N2—C20 | 1.409 (3) | C24—H24 | 0.9500 |
N2—C19 | 1.463 (2) | C25—C26 | 1.376 (4) |
N3—C36 | 1.401 (2) | C25—H25 | 0.9500 |
N3—C29 | 1.401 (3) | C26—C27 | 1.484 (3) |
N3—C28 | 1.454 (3) | C28—H28A | 0.9900 |
C1—C2 | 1.400 (3) | C28—H28B | 0.9900 |
C1—C6 | 1.405 (3) | C29—C30 | 1.477 (3) |
C1—C10 | 1.521 (3) | C30—C35 | 1.387 (3) |
C2—C3 | 1.410 (2) | C30—C31 | 1.387 (3) |
C2—C7 | 1.498 (3) | C31—C32 | 1.395 (4) |
C3—C4 | 1.398 (3) | C31—H31 | 0.9500 |
C3—C19 | 1.523 (3) | C32—C33 | 1.380 (4) |
C4—C5 | 1.404 (3) | C32—H32 | 0.9500 |
C4—C8 | 1.494 (3) | C33—C34 | 1.388 (4) |
C5—C6 | 1.401 (3) | C33—H33 | 0.9500 |
C5—C28 | 1.517 (3) | C34—C35 | 1.383 (3) |
C6—C9 | 1.496 (3) | C34—H34 | 0.9500 |
C7—H7A | 0.9900 | C35—C36 | 1.482 (3) |
C7—H7B | 0.9900 | C1A—C2A | 1.3900 |
C8—H8A | 0.9900 | C1A—C6A | 1.3900 |
C8—H8B | 0.9900 | C1A—C7A | 1.5213 |
C9—H9A | 0.9900 | C2A—C3A | 1.3900 |
C9—H9B | 0.9900 | C2A—H2A | 0.9500 |
C10—H10A | 0.9900 | C3A—C4A | 1.3900 |
C10—H10B | 0.9900 | C3A—H3A | 0.9500 |
C11—C12 | 1.476 (3) | C4A—C5A | 1.3900 |
C12—C17 | 1.378 (3) | C4A—H4A | 0.9500 |
C12—C13 | 1.384 (3) | C5A—C6A | 1.3900 |
C13—C14 | 1.396 (4) | C5A—H5A | 0.9500 |
C13—H13 | 0.9500 | C6A—H6A | 0.9500 |
C14—C15 | 1.385 (5) | C7A—H7A1 | 0.9800 |
C14—H14 | 0.9500 | C7A—H7A2 | 0.9800 |
C15—C16 | 1.402 (4) | C7A—H7A3 | 0.9800 |
C15—H15 | 0.9500 | ||
C18—N1—C11 | 111.52 (18) | H19A—C19—H19B | 107.4 |
C18—N1—C10 | 123.14 (17) | O3—C20—N2 | 124.61 (19) |
C11—N1—C10 | 124.97 (17) | O3—C20—C21 | 129.3 (2) |
C27—N2—C20 | 110.78 (17) | N2—C20—C21 | 106.06 (19) |
C27—N2—C19 | 125.23 (16) | C26—C21—C22 | 121.3 (2) |
C20—N2—C19 | 121.58 (17) | C26—C21—C20 | 108.21 (18) |
C36—N3—C29 | 111.29 (17) | C22—C21—C20 | 130.5 (2) |
C36—N3—C28 | 125.06 (17) | C23—C22—C21 | 117.1 (3) |
C29—N3—C28 | 123.58 (16) | C23—C22—H22 | 121.5 |
C2—C1—C6 | 119.64 (16) | C21—C22—H22 | 121.5 |
C2—C1—C10 | 120.62 (17) | C22—C23—C24 | 121.6 (2) |
C6—C1—C10 | 119.67 (17) | C22—C23—H23 | 119.2 |
C1—C2—C3 | 120.11 (17) | C24—C23—H23 | 119.2 |
C1—C2—C7 | 120.26 (16) | C23—C24—C25 | 121.1 (3) |
C3—C2—C7 | 119.63 (16) | C23—C24—H24 | 119.5 |
C4—C3—C2 | 119.88 (17) | C25—C24—H24 | 119.5 |
C4—C3—C19 | 120.55 (16) | C26—C25—C24 | 117.1 (3) |
C2—C3—C19 | 119.42 (17) | C26—C25—H25 | 121.5 |
C3—C4—C5 | 120.07 (17) | C24—C25—H25 | 121.5 |
C3—C4—C8 | 120.62 (17) | C25—C26—C21 | 121.9 (2) |
C5—C4—C8 | 119.31 (17) | C25—C26—C27 | 129.7 (2) |
C6—C5—C4 | 119.88 (17) | C21—C26—C27 | 108.4 (2) |
C6—C5—C28 | 120.05 (16) | O4—C27—N2 | 125.15 (19) |
C4—C5—C28 | 120.07 (16) | O4—C27—C26 | 128.9 (2) |
C5—C6—C1 | 120.26 (17) | N2—C27—C26 | 105.95 (19) |
C5—C6—C9 | 119.51 (17) | N3—C28—C5 | 112.61 (16) |
C1—C6—C9 | 120.22 (17) | N3—C28—H28A | 109.1 |
C2—C7—Br1 | 110.86 (14) | C5—C28—H28A | 109.1 |
C2—C7—H7A | 109.5 | N3—C28—H28B | 109.1 |
Br1—C7—H7A | 109.5 | C5—C28—H28B | 109.1 |
C2—C7—H7B | 109.5 | H28A—C28—H28B | 107.8 |
Br1—C7—H7B | 109.5 | O5—C29—N3 | 124.4 (2) |
H7A—C7—H7B | 108.1 | O5—C29—C30 | 129.29 (19) |
C4—C8—Br2 | 110.66 (14) | N3—C29—C30 | 106.26 (16) |
C4—C8—H8A | 109.5 | C35—C30—C31 | 122.4 (2) |
Br2—C8—H8A | 109.5 | C35—C30—C29 | 108.11 (18) |
C4—C8—H8B | 109.5 | C31—C30—C29 | 129.5 (2) |
Br2—C8—H8B | 109.5 | C30—C31—C32 | 116.5 (2) |
H8A—C8—H8B | 108.1 | C30—C31—H31 | 121.8 |
C6—C9—Br3 | 110.74 (14) | C32—C31—H31 | 121.8 |
C6—C9—H9A | 109.5 | C33—C32—C31 | 120.9 (2) |
Br3—C9—H9A | 109.5 | C33—C32—H32 | 119.5 |
C6—C9—H9B | 109.5 | C31—C32—H32 | 119.5 |
Br3—C9—H9B | 109.5 | C32—C33—C34 | 122.4 (2) |
H9A—C9—H9B | 108.1 | C32—C33—H33 | 118.8 |
N1—C10—C1 | 115.09 (17) | C34—C33—H33 | 118.8 |
N1—C10—H10A | 108.5 | C35—C34—C33 | 116.9 (2) |
C1—C10—H10A | 108.5 | C35—C34—H34 | 121.6 |
N1—C10—H10B | 108.5 | C33—C34—H34 | 121.6 |
C1—C10—H10B | 108.5 | C34—C35—C30 | 120.9 (2) |
H10A—C10—H10B | 107.5 | C34—C35—C36 | 130.8 (2) |
O1—C11—N1 | 124.2 (2) | C30—C35—C36 | 108.36 (18) |
O1—C11—C12 | 130.1 (2) | O6—C36—N3 | 124.9 (2) |
N1—C11—C12 | 105.73 (17) | O6—C36—C35 | 129.2 (2) |
C17—C12—C13 | 121.7 (2) | N3—C36—C35 | 105.89 (17) |
C17—C12—C11 | 108.37 (19) | C2A—C1A—C6A | 120.0 |
C13—C12—C11 | 129.9 (2) | C2A—C1A—C7A | 125.0 |
C12—C13—C14 | 116.9 (3) | C6A—C1A—C7A | 114.9 |
C12—C13—H13 | 121.5 | C3A—C2A—C1A | 120.0 |
C14—C13—H13 | 121.5 | C3A—C2A—H2A | 120.0 |
C15—C14—C13 | 121.5 (3) | C1A—C2A—H2A | 120.0 |
C15—C14—H14 | 119.3 | C2A—C3A—C4A | 120.0 |
C13—C14—H14 | 119.3 | C2A—C3A—H3A | 120.0 |
C14—C15—C16 | 121.3 (3) | C4A—C3A—H3A | 120.0 |
C14—C15—H15 | 119.4 | C5A—C4A—C3A | 120.0 |
C16—C15—H15 | 119.3 | C5A—C4A—H4A | 120.0 |
C17—C16—C15 | 116.5 (3) | C3A—C4A—H4A | 120.0 |
C17—C16—H16 | 121.8 | C6A—C5A—C4A | 120.0 |
C15—C16—H16 | 121.8 | C6A—C5A—H5A | 120.0 |
C12—C17—C16 | 122.1 (2) | C4A—C5A—H5A | 120.0 |
C12—C17—C18 | 108.37 (19) | C5A—C6A—C1A | 120.0 |
C16—C17—C18 | 129.5 (2) | C5A—C6A—H6A | 120.0 |
O2—C18—N1 | 124.2 (2) | C1A—C6A—H6A | 120.0 |
O2—C18—C17 | 129.84 (19) | C1A—C7A—H7A1 | 109.5 |
N1—C18—C17 | 105.98 (17) | C1A—C7A—H7A2 | 109.5 |
N2—C19—C3 | 116.12 (16) | H7A1—C7A—H7A2 | 109.5 |
N2—C19—H19A | 108.3 | C1A—C7A—H7A3 | 109.5 |
C3—C19—H19A | 108.3 | H7A1—C7A—H7A3 | 109.5 |
N2—C19—H19B | 108.3 | H7A2—C7A—H7A3 | 109.5 |
C3—C19—H19B | 108.3 | ||
C6—C1—C2—C3 | 3.0 (3) | C19—N2—C20—O3 | −9.9 (3) |
C10—C1—C2—C3 | −174.19 (18) | C27—N2—C20—C21 | 7.1 (2) |
C6—C1—C2—C7 | −176.32 (19) | C19—N2—C20—C21 | 170.34 (17) |
C10—C1—C2—C7 | 6.5 (3) | O3—C20—C21—C26 | 176.7 (2) |
C1—C2—C3—C4 | 0.6 (3) | N2—C20—C21—C26 | −3.6 (2) |
C7—C2—C3—C4 | 179.86 (18) | O3—C20—C21—C22 | −3.3 (4) |
C1—C2—C3—C19 | −174.93 (18) | N2—C20—C21—C22 | 176.4 (2) |
C7—C2—C3—C19 | 4.3 (3) | C26—C21—C22—C23 | 0.9 (4) |
C2—C3—C4—C5 | −3.7 (3) | C20—C21—C22—C23 | −179.1 (2) |
C19—C3—C4—C5 | 171.81 (18) | C21—C22—C23—C24 | −1.1 (4) |
C2—C3—C4—C8 | 175.78 (18) | C22—C23—C24—C25 | 0.6 (4) |
C19—C3—C4—C8 | −8.8 (3) | C23—C24—C25—C26 | 0.2 (4) |
C3—C4—C5—C6 | 3.2 (3) | C24—C25—C26—C21 | −0.4 (4) |
C8—C4—C5—C6 | −176.28 (18) | C24—C25—C26—C27 | −179.3 (2) |
C3—C4—C5—C28 | −176.88 (18) | C22—C21—C26—C25 | −0.1 (4) |
C8—C4—C5—C28 | 3.7 (3) | C20—C21—C26—C25 | 179.9 (2) |
C4—C5—C6—C1 | 0.4 (3) | C22—C21—C26—C27 | 179.0 (2) |
C28—C5—C6—C1 | −179.56 (18) | C20—C21—C26—C27 | −1.0 (2) |
C4—C5—C6—C9 | −178.73 (19) | C20—N2—C27—O4 | 170.9 (2) |
C28—C5—C6—C9 | 1.3 (3) | C19—N2—C27—O4 | 8.4 (3) |
C2—C1—C6—C5 | −3.4 (3) | C20—N2—C27—C26 | −7.7 (2) |
C10—C1—C6—C5 | 173.72 (18) | C19—N2—C27—C26 | −170.18 (18) |
C2—C1—C6—C9 | 175.67 (19) | C25—C26—C27—O4 | 5.7 (4) |
C10—C1—C6—C9 | −7.2 (3) | C21—C26—C27—O4 | −173.3 (2) |
C1—C2—C7—Br1 | 93.3 (2) | C25—C26—C27—N2 | −175.8 (2) |
C3—C2—C7—Br1 | −85.9 (2) | C21—C26—C27—N2 | 5.3 (2) |
C3—C4—C8—Br2 | 92.48 (19) | C36—N3—C28—C5 | −126.16 (18) |
C5—C4—C8—Br2 | −88.1 (2) | C29—N3—C28—C5 | 57.0 (2) |
C5—C6—C9—Br3 | −99.78 (19) | C6—C5—C28—N3 | 72.1 (2) |
C1—C6—C9—Br3 | 81.1 (2) | C4—C5—C28—N3 | −107.8 (2) |
C18—N1—C10—C1 | 129.25 (19) | C36—N3—C29—O5 | 176.44 (19) |
C11—N1—C10—C1 | −58.3 (2) | C28—N3—C29—O5 | −6.3 (3) |
C2—C1—C10—N1 | −68.4 (2) | C36—N3—C29—C30 | −3.0 (2) |
C6—C1—C10—N1 | 114.4 (2) | C28—N3—C29—C30 | 174.23 (16) |
C18—N1—C11—O1 | 177.67 (19) | O5—C29—C30—C35 | −177.2 (2) |
C10—N1—C11—O1 | 4.5 (3) | N3—C29—C30—C35 | 2.2 (2) |
C18—N1—C11—C12 | −1.2 (2) | O5—C29—C30—C31 | 3.0 (4) |
C10—N1—C11—C12 | −174.34 (17) | N3—C29—C30—C31 | −177.6 (2) |
O1—C11—C12—C17 | −177.0 (2) | C35—C30—C31—C32 | 0.3 (3) |
N1—C11—C12—C17 | 1.7 (2) | C29—C30—C31—C32 | −179.9 (2) |
O1—C11—C12—C13 | 0.7 (4) | C30—C31—C32—C33 | 0.5 (3) |
N1—C11—C12—C13 | 179.4 (2) | C31—C32—C33—C34 | −0.7 (4) |
C17—C12—C13—C14 | 0.3 (3) | C32—C33—C34—C35 | 0.0 (3) |
C11—C12—C13—C14 | −177.1 (2) | C33—C34—C35—C30 | 0.8 (3) |
C12—C13—C14—C15 | 0.7 (4) | C33—C34—C35—C36 | −179.4 (2) |
C13—C14—C15—C16 | −1.1 (4) | C31—C30—C35—C34 | −1.0 (3) |
C14—C15—C16—C17 | 0.4 (4) | C29—C30—C35—C34 | 179.18 (19) |
C13—C12—C17—C16 | −1.1 (3) | C31—C30—C35—C36 | 179.16 (19) |
C11—C12—C17—C16 | 176.8 (2) | C29—C30—C35—C36 | −0.7 (2) |
C13—C12—C17—C18 | −179.57 (19) | C29—N3—C36—O6 | −177.11 (19) |
C11—C12—C17—C18 | −1.6 (2) | C28—N3—C36—O6 | 5.7 (3) |
C15—C16—C17—C12 | 0.7 (3) | C29—N3—C36—C35 | 2.6 (2) |
C15—C16—C17—C18 | 178.8 (2) | C28—N3—C36—C35 | −174.60 (17) |
C11—N1—C18—O2 | −179.56 (19) | C34—C35—C36—O6 | −1.3 (4) |
C10—N1—C18—O2 | −6.2 (3) | C30—C35—C36—O6 | 178.6 (2) |
C11—N1—C18—C17 | 0.2 (2) | C34—C35—C36—N3 | 179.1 (2) |
C10—N1—C18—C17 | 173.51 (17) | C30—C35—C36—N3 | −1.1 (2) |
C12—C17—C18—O2 | −179.3 (2) | C6A—C1A—C2A—C3A | 0.0 |
C16—C17—C18—O2 | 2.4 (4) | C7A—C1A—C2A—C3A | −176.9 |
C12—C17—C18—N1 | 0.9 (2) | C1A—C2A—C3A—C4A | 0.0 |
C16—C17—C18—N1 | −177.4 (2) | C2A—C3A—C4A—C5A | 0.0 |
C27—N2—C19—C3 | −74.7 (2) | C3A—C4A—C5A—C6A | 0.0 |
C20—N2—C19—C3 | 124.55 (19) | C4A—C5A—C6A—C1A | 0.0 |
C4—C3—C19—N2 | 106.5 (2) | C2A—C1A—C6A—C5A | 0.0 |
C2—C3—C19—N2 | −78.0 (2) | C7A—C1A—C6A—C5A | 177.2 |
C27—N2—C20—O3 | −173.1 (2) |
Cg1 and Cg2 are centroids of the C1A–C6A and C21–C26 benzene rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7B···O3 | 0.99 | 2.47 | 3.309 (3) | 142 |
C8—H8A···O4 | 0.99 | 2.18 | 3.061 (3) | 147 |
C8—H8B···O5 | 0.99 | 2.36 | 3.036 (3) | 125 |
C8—H8B···O6i | 0.99 | 2.58 | 3.477 (3) | 151 |
C9—H9A···O1 | 0.99 | 2.54 | 3.308 (3) | 135 |
C10—H10B···Br3 | 0.99 | 2.77 | 3.519 (2) | 133 |
C14—H14···O5ii | 0.95 | 2.49 | 3.080 (3) | 121 |
C19—H19A···Br1 | 0.99 | 2.89 | 3.642 (2) | 133 |
C24—H24···O2iii | 0.95 | 2.43 | 3.290 (3) | 150 |
C28—H28A···O6i | 0.99 | 2.58 | 3.344 (2) | 134 |
C33—H33···Br2iv | 0.95 | 2.77 | 3.590 (3) | 145 |
C22—H22···Cg1v | 0.95 | 2.66 | 3.599 (3) | 169 |
C6A—H6A···Cg2 | 0.95 | 2.99 | 3.795 (3) | 143 |
Symmetry codes: (i) x+1/2, −y+1/2, z; (ii) x−1, y, z−1; (iii) −x+2, −y, z+1/2; (iv) x−1/2, −y+1/2, z+1; (v) −x+2, −y−1, z+1/2. |
Cg1 and Cg2 are centroids of the C1A–C6A and C21–C26 benzene rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7B···O3 | 0.99 | 2.47 | 3.309 (3) | 141.8 |
C8—H8A···O4 | 0.99 | 2.18 | 3.061 (3) | 147.4 |
C8—H8B···O5 | 0.99 | 2.36 | 3.036 (3) | 124.9 |
C8—H8B···O6i | 0.99 | 2.58 | 3.477 (3) | 151.1 |
C9—H9A···O1 | 0.99 | 2.54 | 3.308 (3) | 134.8 |
C10—H10B···Br3 | 0.99 | 2.77 | 3.519 (2) | 132.7 |
C14—H14···O5ii | 0.95 | 2.49 | 3.080 (3) | 120.7 |
C19—H19A···Br1 | 0.99 | 2.89 | 3.642 (2) | 133.3 |
C24—H24···O2iii | 0.95 | 2.43 | 3.290 (3) | 149.9 |
C28—H28A···O6i | 0.99 | 2.58 | 3.344 (2) | 133.7 |
C33—H33···Br2iv | 0.95 | 2.77 | 3.590 (3) | 144.8 |
C22—H22···Cg1v | 0.95 | 2.66 | 3.599 (3) | 168.5 |
C6A—H6A···Cg2 | 0.95 | 2.99 | 3.795 (3) | 142.9 |
Symmetry codes: (i) x+1/2, −y+1/2, z; (ii) x−1, y, z−1; (iii) −x+2, −y, z+1/2; (iv) x−1/2, −y+1/2, z+1; (v) −x+2, −y−1, z+1/2. |
Our interest in the title compound, C36H24N3O6Br3, arises from its use as a precursor in the synthesis of novel heteroditopic artificial receptors containing a hexasubstituted benzene scaffold. The synthesis of ditopic receptors, which interact simultaneously with cationic and anionic guests in so called ion-pair recognition processes, is a rapidly developing area of research (McConnell & Beer, 2012). A number of ditopic receptors based on a macrocylic or acyclic scaffold have been designed and studied (Kinnear et al. (1994), Kirkovits et al. (2001), Hossain & Schneider (1998), Tsukube et al. (1999) and Smith (2010)) Interesting applications, such as binding of amino acids in their zwitterionic state, salt extraction and membrane transport, have been reported in the literature (for a recent review, see McConnell & Beer, 2012). In this context, the title compound is a particularly useful building block for the construction of a large number of receptors with different recognition units, because it provides a base for many synthetic modifications of the molecule structure. Crystallization of the title compound from toluene yields a 1:1 solvent complex (Fig. 1). According to the three-dimensional arrangement of the substituent groups around the periphery of the central arene ring, the conformational isomer of the receptor can be described as 1-down, 3,5-up tris((phthalimidomethyl), 2,4-down, 6-up tris(bromomethyl)benzene. The mean planes of the phthalimido moieties are inclined at angles of 77.0 (1), 63.0 (1) and 77.8 (1)° with reference to the plane of the benzene ring. The torsion angles given by the atomic sequences C1—C2—C7—Br1, C3—C4—C8—Br2 and C5—C6—C9—Br3 are 93.3 (2), 92.5 (2) and -99.8 (2) °, respectively. The host lattice is stabilized by non-conventional hydrogen bonds of the C—H···N [d(H···N) 2.55 Å], C—H···O [d(H···O) 2.18–2.58 Å] and C—H···Br type [d(H···Br) 2.77, 2.89 Å]. Moreover, the intermolecular distance O1···Br2 [3.306 (3) Å], which is less than the sum of van der Waals radii of the respective atoms [3.37 Å], indicates the presence of a weak C=O···Br halogen bond. As depicted in Fig. 2, the interactions between the receptor and the solvent molecule are reduced to weak C—H···π contacts with the aromatic ring of the toluene molecule and one of the phthalimido units of the receptor acting as acceptors [C22—H22···cg1 2.66 Å, 169 °, C6A—H6A···cg2 2.99 Å, 143 °]. Taking into account this kind of interactions, the crystal structure can be regarded as being composed of infinite strands of 1:1 complex units running along the crystallographic a-axis (Fig. 3).