Literature DB >> 21580692

5,11,17,23-Tetra-bromo-25,26,27,28-tetra-kis(4-tolyl-sulfon-yloxy)-2,8,14,20-tetra-thia-calix[4]arene dichloro-methane solvate.

Yue-Feng Chen1, Yang Liu, Jian-Ping Ma, Dian-Shun Guo.   

Abstract

In the crystal structure of the title compound, C(52)H(36)Br(4)O(12)S(8)·CH(2)Cl(2), the thia-calix[4]arene unit adopts a 1,3-alternate conformation with an intra-molecular C-H⋯O hydrogen bond and four C-H⋯π inter-actions, with the four 4-MeC(6)H(4)SO(3) groups located alternately above and below the virtual plane (R) defined by the four bridging S atoms. The benzene ring of each 4-MeC(6)H(4)SO(3) unit is nearly perpendicular to one of the two neighboring phenol rings with inter-planar angles varying from 72.97 (13) to 78.70 (13)°, while the dihedral angles between the plane (R) and the phenol rings range from 83.04 (7) to 84.30 (9)°. In the supra-molecular structure, a solvent-bridged dimer composed of two main mol-ecules is formed by four inter-molecular C-H⋯O hydrogen bonds and locally creates an R(4) (4)(26) motif. Such dimers associate further into chains by inter-dimer C-Cl⋯O short contacts [Cl⋯O 3.182 (5) Å]. Finally, these chains are linked into a two-dimensional network by a combination of inter-chain C-Br⋯O inter-actions [Br⋯O = 3.183 (3) and 2.966 (4) Å] as well as C-H⋯O hydrogen bonds.

Entities:  

Year:  2010        PMID： 21580692      PMCID： PMC2983853          DOI： 10.1107/S1600536810009554

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For general background to the chemistry of thia­calix[4]arenes, see: Kumagai et al. (1997 ▶); Shokova & Kovalev (2003 ▶); Lhoták (2004 ▶); Morohashi et al. (2006 ▶); Guo et al. (2007 ▶). For the synthesis and related structures, see: Lhoták et al. (2001 ▶); Kasyan et al. (2003 ▶); Xu et al. (2008 ▶). For C—H⋯π inter­actions, see: Tsuzuki et al. (2000 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For C—X⋯O (X = Cl, Br) short contacts, see: Lommerse et al. (1996 ▶); Metrangolo & Resnati (2001 ▶). For atomic radii, see: Bondi (1964 ▶).

Experimental

Crystal data

C52H36Br4O12S8·CH2Cl2 M = 1513.85 Monoclinic, a = 12.6945 (14) Å b = 20.793 (2) Å c = 23.190 (3) Å β = 103.350 (2)° V = 5955.8 (12) Å3 Z = 4 Mo Kα radiation μ = 3.13 mm−1 T = 173 K 0.30 × 0.21 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.453, T max = 0.705 30976 measured reflections 11092 independent reflections 7807 reflections with I > 2σ(I) R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.040 wR(F 2) = 0.107 S = 1.06 11092 reflections 715 parameters 6 restraints H-atom parameters constrained Δρmax = 0.86 e Å−3 Δρmin = −0.68 e Å−3 Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810009554/bg2335sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009554/bg2335Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C52H36Br4O12S8·CH2Cl2F(000) = 3016
Mr = 1513.85Dx = 1.688 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7685 reflections
a = 12.6945 (14) Åθ = 2.4–26.5°
b = 20.793 (2) ŵ = 3.13 mm−1
c = 23.190 (3) ÅT = 173 K
β = 103.350 (2)°Block, colourless
V = 5955.8 (12) Å30.30 × 0.21 × 0.12 mm
Z = 4
Bruker SMART CCD area-detector diffractometer11092 independent reflections
Radiation source: fine-focus sealed tube7807 reflections with I > 2σ(I)
graphiteRint = 0.039
phi and ω scansθmax = 25.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 1999)h = −10→15
Tmin = 0.453, Tmax = 0.705k = −25→25
30976 measured reflectionsl = −27→28
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0524P)2] where P = (Fo2 + 2Fc2)/3
11092 reflections(Δ/σ)max = 0.002
715 parametersΔρmax = 0.86 e Å−3
6 restraintsΔρmin = −0.68 e Å−3
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.
xyzUiso*/Ueq
Br10.43943 (3)1.109304 (19)0.27234 (2)0.04887 (13)
Br31.02769 (5)0.78011 (2)0.30945 (3)0.07916 (19)
Br40.95485 (4)0.83143 (2)0.11261 (3)0.07435 (18)
C10.7126 (4)0.72823 (17)0.15746 (18)0.0462 (10)
H10.75600.72130.19620.055*
C20.7437 (4)0.70462 (18)0.1088 (2)0.0532 (11)
H20.80950.68120.11420.064*
C30.6821 (4)0.7139 (2)0.0523 (2)0.0566 (12)
C40.5861 (4)0.7474 (2)0.0453 (2)0.0592 (13)
H40.54220.75360.00650.071*
C50.5526 (4)0.77185 (18)0.09320 (19)0.0499 (11)
H50.48630.79480.08780.060*
C60.6169 (3)0.76234 (16)0.14918 (17)0.0395 (9)
C70.7211 (5)0.6888 (3)−0.0003 (2)0.0857 (18)
H7A0.70780.6424−0.00420.129*
H7B0.79880.69720.00560.129*
H7C0.68180.7106−0.03640.129*
C80.5929 (3)0.91727 (15)0.23204 (15)0.0294 (8)
C90.5510 (3)0.95961 (16)0.18624 (15)0.0289 (8)
C100.5032 (3)1.01623 (16)0.19828 (16)0.0320 (8)
H100.47441.04560.16730.038*
C110.4978 (3)1.02969 (16)0.25583 (17)0.0336 (8)
C120.5404 (3)0.98801 (16)0.30179 (16)0.0327 (8)
H120.53620.99810.34120.039*
C130.5890 (3)0.93175 (16)0.29019 (16)0.0315 (8)
C140.4205 (3)1.08761 (18)0.03965 (16)0.0368 (9)
H140.43551.05570.01330.044*
C150.3154 (3)1.1000 (2)0.04305 (18)0.0469 (10)
H150.25761.07770.01760.056*
C160.2926 (4)1.1446 (2)0.0831 (2)0.0539 (12)
C170.3775 (4)1.1780 (2)0.11757 (19)0.0545 (12)
H170.36291.20910.14460.065*
C180.4823 (4)1.16789 (19)0.11438 (17)0.0478 (10)
H180.53961.19180.13860.057*
C190.5034 (3)1.12220 (17)0.07513 (16)0.0329 (8)
C200.1768 (4)1.1552 (3)0.0878 (3)0.0891 (19)
H20A0.16731.13800.12560.134*
H20B0.12751.13310.05500.134*
H20C0.16071.20130.08570.134*
C210.7461 (3)1.01215 (16)0.12285 (14)0.0301 (8)
C220.6975 (3)0.95190 (17)0.11682 (15)0.0319 (8)
C230.7602 (3)0.89818 (17)0.11292 (16)0.0362 (9)
H230.72810.85670.10800.043*
C240.8693 (3)0.90537 (17)0.11629 (17)0.0399 (9)
C250.9191 (3)0.96488 (17)0.12485 (16)0.0354 (9)
H250.99480.96870.12800.043*
C260.8572 (3)1.01866 (16)0.12870 (15)0.0303 (8)
C270.9046 (3)1.10806 (16)0.21337 (16)0.0308 (8)
C280.8342 (3)1.15600 (16)0.22221 (16)0.0337 (8)
H280.79581.18100.18990.040*
C290.8207 (3)1.16681 (17)0.27889 (18)0.0385 (9)
C300.8731 (3)1.13048 (17)0.32628 (17)0.0373 (9)
H300.86191.13860.36470.045*
C310.9428 (3)1.08162 (16)0.31765 (15)0.0312 (8)
C320.9604 (3)1.07211 (15)0.26131 (15)0.0292 (8)
C331.2307 (3)0.99037 (18)0.30119 (17)0.0382 (9)
C341.2480 (3)0.9286 (2)0.2833 (2)0.0501 (11)
H341.21920.91570.24350.060*
C351.3071 (4)0.8862 (2)0.3234 (3)0.0652 (14)
H351.31840.84370.31110.078*
C361.3498 (4)0.9038 (3)0.3804 (2)0.0649 (14)
C371.3352 (4)0.9664 (3)0.39852 (19)0.0617 (13)
H371.36660.97930.43810.074*
C381.2746 (3)1.0102 (2)0.35870 (18)0.0491 (10)
H381.26361.05280.37080.059*
C391.4138 (5)0.8562 (3)0.4245 (3)0.0962 (19)
H39A1.36370.82770.43870.144*
H39B1.45840.87960.45810.144*
H39C1.46060.83060.40520.144*
C400.9434 (3)0.95975 (17)0.36111 (15)0.0347 (8)
C411.0005 (3)0.90881 (19)0.34477 (17)0.0423 (10)
H411.07360.91430.34220.051*
C420.9503 (4)0.85022 (19)0.33231 (18)0.0475 (11)
C430.8436 (3)0.84099 (18)0.33341 (17)0.0423 (10)
H430.81000.80040.32310.051*
C440.7854 (3)0.89146 (17)0.34975 (16)0.0350 (9)
C450.8365 (3)0.95058 (16)0.36448 (15)0.0330 (8)
C460.8028 (3)1.08666 (18)0.46528 (16)0.0371 (9)
C470.7283 (3)1.1358 (2)0.44931 (18)0.0463 (10)
H470.65651.12670.42800.056*
C480.7595 (4)1.1981 (2)0.46472 (19)0.0510 (11)
H480.70861.23200.45370.061*
C490.8637 (4)1.2122 (2)0.49601 (19)0.0519 (11)
C500.9368 (4)1.1623 (2)0.51078 (18)0.0512 (11)
H501.00861.17150.53190.061*
C510.9084 (3)1.0994 (2)0.49574 (17)0.0451 (10)
H510.95981.06560.50600.054*
C520.8968 (4)1.2802 (2)0.5135 (2)0.0706 (15)
H52A0.93421.28140.55550.106*
H52B0.83231.30760.50710.106*
H52C0.94541.29600.48940.106*
C530.2434 (4)0.9546 (2)0.0855 (2)0.0602 (12)
H53A0.30400.96360.06640.072*
H53B0.24420.98810.11600.072*
Cl10.12058 (11)0.95976 (7)0.03170 (6)0.0723 (4)
Cl20.26337 (14)0.88004 (7)0.11968 (7)0.0922 (5)
O31.1686 (2)1.10828 (12)0.27040 (13)0.0498 (7)
O41.1667 (2)1.02640 (14)0.19338 (12)0.0513 (7)
O50.6387 (2)1.07104 (15)0.01904 (12)0.0562 (8)
O60.6901 (2)1.16960 (14)0.07755 (16)0.0691 (10)
O70.8372 (2)0.96353 (13)0.48243 (11)0.0497 (7)
O80.6506 (2)1.00265 (14)0.44481 (12)0.0502 (7)
O90.6457 (2)0.86122 (10)0.21968 (10)0.0335 (6)
O101.03130 (18)1.02329 (11)0.25253 (10)0.0317 (5)
O110.68364 (19)1.06686 (11)0.12749 (10)0.0326 (6)
O120.77790 (19)1.00232 (11)0.38031 (10)0.0337 (6)
S10.57961 (10)0.79407 (4)0.21118 (5)0.0466 (3)
S20.55608 (7)0.94214 (4)0.11169 (4)0.0335 (2)
S30.63585 (8)1.10942 (5)0.06895 (5)0.0420 (2)
S40.92238 (8)1.09501 (4)0.14036 (4)0.0339 (2)
S51.15421 (7)1.04388 (4)0.25031 (4)0.0362 (2)
S61.01038 (8)1.03516 (5)0.37934 (4)0.0379 (2)
S70.76318 (8)1.00733 (5)0.44783 (4)0.0392 (2)
S80.64672 (8)0.88001 (4)0.35001 (4)0.0373 (2)
Br20.72092 (4)1.23092 (2)0.29012 (2)0.06032 (15)
O10.4687 (3)0.80924 (14)0.19888 (16)0.0672 (9)
O20.6272 (3)0.75471 (13)0.26017 (13)0.0712 (10)
U11U22U33U12U13U23
Br10.0508 (3)0.0352 (2)0.0657 (3)0.01028 (19)0.0236 (2)−0.00070 (19)
Br30.0827 (4)0.0475 (3)0.1215 (5)0.0245 (3)0.0525 (4)−0.0012 (3)
Br40.0645 (3)0.0421 (3)0.1291 (5)0.0083 (2)0.0485 (3)−0.0082 (3)
C10.063 (3)0.0278 (19)0.042 (2)−0.001 (2)−0.001 (2)−0.0005 (17)
C20.067 (3)0.032 (2)0.063 (3)0.008 (2)0.020 (2)−0.005 (2)
C30.088 (4)0.036 (2)0.047 (3)−0.004 (2)0.018 (3)−0.009 (2)
C40.088 (4)0.039 (2)0.042 (3)−0.010 (2)−0.002 (2)−0.008 (2)
C50.055 (3)0.032 (2)0.056 (3)−0.005 (2)0.000 (2)−0.002 (2)
C60.052 (3)0.0226 (18)0.044 (2)−0.0067 (18)0.0112 (19)−0.0026 (16)
C70.137 (6)0.071 (3)0.058 (3)0.007 (4)0.039 (3)−0.017 (3)
C80.0299 (19)0.0239 (17)0.035 (2)−0.0016 (15)0.0095 (16)0.0010 (15)
C90.0266 (19)0.0302 (18)0.030 (2)−0.0076 (15)0.0079 (15)−0.0013 (15)
C100.0252 (19)0.0309 (19)0.040 (2)−0.0003 (15)0.0080 (16)0.0081 (16)
C110.029 (2)0.0266 (18)0.047 (2)0.0013 (15)0.0130 (17)−0.0020 (16)
C120.032 (2)0.0342 (19)0.034 (2)−0.0020 (16)0.0124 (16)−0.0034 (16)
C130.032 (2)0.0303 (19)0.034 (2)−0.0035 (16)0.0101 (16)0.0032 (16)
C140.037 (2)0.042 (2)0.031 (2)0.0025 (18)0.0068 (17)0.0034 (17)
C150.040 (2)0.055 (3)0.042 (2)−0.002 (2)0.0028 (19)0.006 (2)
C160.049 (3)0.064 (3)0.054 (3)0.017 (2)0.023 (2)0.020 (2)
C170.073 (3)0.052 (3)0.041 (3)0.026 (2)0.018 (2)0.000 (2)
C180.057 (3)0.044 (2)0.038 (2)0.007 (2)0.002 (2)−0.0011 (19)
C190.032 (2)0.0336 (19)0.032 (2)0.0029 (16)0.0068 (16)0.0079 (16)
C200.060 (3)0.109 (5)0.108 (5)0.034 (3)0.040 (3)0.035 (4)
C210.035 (2)0.0316 (19)0.0241 (19)0.0019 (16)0.0073 (15)0.0024 (15)
C220.037 (2)0.037 (2)0.0225 (18)−0.0049 (17)0.0066 (15)−0.0025 (15)
C230.045 (2)0.0304 (19)0.037 (2)−0.0047 (17)0.0159 (18)−0.0014 (16)
C240.047 (2)0.034 (2)0.043 (2)0.0083 (18)0.0188 (19)−0.0041 (17)
C250.035 (2)0.040 (2)0.034 (2)0.0008 (17)0.0138 (17)−0.0012 (17)
C260.035 (2)0.0304 (18)0.0269 (19)−0.0054 (16)0.0096 (15)−0.0014 (15)
C270.031 (2)0.0266 (18)0.036 (2)−0.0074 (15)0.0106 (16)−0.0025 (15)
C280.034 (2)0.0278 (18)0.041 (2)−0.0032 (16)0.0124 (17)0.0024 (16)
C290.033 (2)0.0295 (19)0.055 (3)0.0014 (16)0.0162 (19)−0.0009 (18)
C300.039 (2)0.036 (2)0.039 (2)−0.0001 (18)0.0154 (18)−0.0060 (17)
C310.030 (2)0.0311 (18)0.032 (2)−0.0011 (16)0.0057 (15)−0.0013 (15)
C320.0292 (19)0.0236 (17)0.036 (2)−0.0025 (15)0.0094 (16)−0.0028 (15)
C330.032 (2)0.043 (2)0.042 (2)0.0081 (18)0.0144 (17)−0.0014 (18)
C340.049 (3)0.047 (2)0.058 (3)0.005 (2)0.020 (2)0.000 (2)
C350.063 (3)0.053 (3)0.089 (4)0.021 (2)0.036 (3)0.016 (3)
C360.054 (3)0.079 (4)0.072 (4)0.028 (3)0.036 (3)0.033 (3)
C370.043 (3)0.107 (4)0.036 (3)0.009 (3)0.012 (2)0.010 (3)
C380.041 (2)0.062 (3)0.046 (3)0.005 (2)0.014 (2)−0.005 (2)
C390.091 (4)0.111 (4)0.093 (4)0.030 (3)0.035 (3)0.044 (3)
C400.041 (2)0.037 (2)0.027 (2)0.0070 (17)0.0105 (16)0.0078 (16)
C410.041 (2)0.047 (2)0.043 (2)0.0112 (19)0.0201 (19)0.0078 (19)
C420.057 (3)0.039 (2)0.051 (3)0.020 (2)0.021 (2)0.0051 (19)
C430.057 (3)0.033 (2)0.039 (2)0.0083 (19)0.016 (2)0.0041 (17)
C440.041 (2)0.034 (2)0.031 (2)0.0066 (17)0.0105 (17)0.0056 (16)
C450.041 (2)0.0326 (19)0.0262 (19)0.0104 (17)0.0091 (16)0.0059 (15)
C460.040 (2)0.041 (2)0.033 (2)0.0027 (18)0.0123 (17)−0.0044 (17)
C470.040 (2)0.052 (3)0.048 (3)0.005 (2)0.0128 (19)−0.008 (2)
C480.053 (3)0.047 (2)0.057 (3)0.009 (2)0.022 (2)−0.005 (2)
C490.064 (3)0.052 (3)0.048 (3)−0.008 (2)0.029 (2)−0.014 (2)
C500.043 (3)0.069 (3)0.042 (3)−0.008 (2)0.010 (2)−0.011 (2)
C510.050 (3)0.050 (2)0.034 (2)0.006 (2)0.0080 (19)−0.0065 (19)
C520.084 (4)0.057 (3)0.077 (4)−0.018 (3)0.032 (3)−0.023 (3)
C530.063 (3)0.071 (3)0.054 (3)0.004 (3)0.028 (2)−0.005 (2)
Cl10.0642 (8)0.0817 (9)0.0734 (9)0.0079 (7)0.0210 (7)0.0129 (7)
Cl20.1032 (12)0.0880 (10)0.0814 (11)0.0135 (9)0.0135 (8)0.0221 (8)
O30.0345 (16)0.0359 (15)0.079 (2)−0.0035 (12)0.0133 (14)−0.0007 (14)
O40.0414 (17)0.076 (2)0.0404 (16)0.0152 (15)0.0182 (13)0.0060 (14)
O50.0519 (18)0.087 (2)0.0340 (16)0.0226 (16)0.0194 (13)0.0147 (15)
O60.0445 (19)0.0490 (18)0.108 (3)−0.0096 (15)0.0045 (17)0.0377 (18)
O70.064 (2)0.0514 (17)0.0335 (16)0.0069 (15)0.0114 (13)0.0064 (13)
O80.0486 (18)0.0607 (18)0.0476 (17)−0.0062 (15)0.0242 (14)−0.0130 (14)
O90.0419 (15)0.0242 (12)0.0362 (14)−0.0009 (11)0.0124 (12)−0.0009 (10)
O100.0299 (13)0.0293 (13)0.0365 (14)0.0017 (10)0.0088 (11)−0.0030 (10)
O110.0349 (14)0.0299 (13)0.0316 (14)0.0035 (11)0.0047 (11)0.0047 (10)
O120.0375 (15)0.0351 (13)0.0298 (14)0.0077 (11)0.0106 (11)0.0000 (11)
S10.0672 (8)0.0267 (5)0.0518 (7)−0.0111 (5)0.0257 (6)−0.0016 (4)
S20.0339 (5)0.0351 (5)0.0306 (5)−0.0054 (4)0.0057 (4)0.0000 (4)
S30.0364 (6)0.0448 (6)0.0452 (6)0.0024 (5)0.0104 (5)0.0167 (5)
S40.0348 (5)0.0349 (5)0.0333 (5)−0.0059 (4)0.0106 (4)0.0016 (4)
S50.0310 (5)0.0398 (5)0.0397 (6)0.0021 (4)0.0124 (4)0.0005 (4)
S60.0362 (5)0.0461 (5)0.0315 (5)0.0035 (4)0.0082 (4)0.0009 (4)
S70.0444 (6)0.0439 (5)0.0321 (5)0.0015 (5)0.0146 (4)−0.0026 (4)
S80.0449 (6)0.0352 (5)0.0335 (5)0.0013 (4)0.0127 (4)0.0074 (4)
Br20.0705 (3)0.0490 (3)0.0703 (3)0.0274 (2)0.0344 (3)0.0062 (2)
O10.058 (2)0.0509 (18)0.103 (3)−0.0244 (16)0.0409 (19)−0.0173 (18)
O20.140 (3)0.0304 (15)0.049 (2)−0.0058 (18)0.034 (2)0.0075 (14)
Br1—C111.888 (3)C30—C311.391 (5)
Br3—C421.900 (4)C30—H300.9500
Br4—C241.896 (4)C31—C321.389 (5)
C1—C21.370 (6)C31—S61.775 (4)
C1—C61.381 (5)C32—O101.403 (4)
C1—H10.9500C33—C341.382 (5)
C2—C31.376 (6)C33—C381.384 (5)
C2—H20.9500C33—S51.745 (4)
C3—C41.380 (7)C34—C351.373 (6)
C3—C71.510 (6)C34—H340.9500
C4—C51.377 (6)C35—C361.357 (7)
C4—H40.9500C35—H350.9500
C5—C61.379 (6)C36—C371.394 (7)
C5—H50.9500C36—C391.518 (7)
C6—S11.744 (4)C37—C381.395 (6)
C7—H7A0.9800C37—H370.9500
C7—H7B0.9800C38—H380.9500
C7—H7C0.9800C39—H39A0.9800
C8—C91.387 (5)C39—H39B0.9800
C8—C131.394 (5)C39—H39C0.9800
C8—O91.407 (4)C40—C411.385 (5)
C9—C101.382 (5)C40—C451.391 (5)
C9—S21.782 (3)C40—S61.787 (4)
C10—C111.381 (5)C41—C421.374 (6)
C10—H100.9500C41—H410.9500
C11—C121.383 (5)C42—C431.375 (6)
C12—C131.377 (5)C43—C441.386 (5)
C12—H120.9500C43—H430.9500
C13—S81.775 (4)C44—C451.395 (5)
C14—C151.378 (5)C44—S81.778 (4)
C14—C191.379 (5)C45—O121.404 (4)
C14—H140.9500C46—C471.383 (5)
C15—C161.389 (6)C46—C511.389 (6)
C15—H150.9500C46—S71.744 (4)
C16—C171.373 (6)C47—C481.378 (6)
C16—C201.515 (6)C47—H470.9500
C17—C181.365 (6)C48—C491.385 (6)
C17—H170.9500C48—H480.9500
C18—C191.384 (5)C49—C501.383 (6)
C18—H180.9500C49—C521.504 (6)
C19—S31.741 (4)C50—C511.380 (6)
C20—H20A0.9800C50—H500.9500
C20—H20B0.9800C51—H510.9500
C20—H20C0.9800C52—H52A0.9800
C21—C221.389 (5)C52—H52B0.9800
C21—C261.391 (5)C52—H52C0.9800
C21—O111.405 (4)C53—Cl21.734 (5)
C22—C231.387 (5)C53—Cl11.760 (5)
C22—S21.783 (4)C53—H53A0.9900
C23—C241.378 (5)C53—H53B0.9900
C23—H230.9500O3—S51.416 (3)
C24—C251.383 (5)O4—S51.413 (3)
C25—C261.382 (5)O5—S31.413 (3)
C25—H250.9500O6—S31.420 (3)
C26—S41.782 (3)O7—S71.417 (3)
C27—C281.385 (5)O8—S71.418 (3)
C27—C321.390 (5)O9—S11.618 (2)
C27—S41.780 (4)O10—S51.630 (2)
C28—C291.383 (5)O11—S31.617 (2)
C28—H280.9500O12—S71.623 (2)
C29—C301.372 (5)S1—O11.407 (3)
C29—Br21.898 (3)S1—O21.417 (3)
C2—C1—C6118.8 (4)C34—C33—S5119.4 (3)
C2—C1—H1120.6C38—C33—S5119.9 (3)
C6—C1—H1120.6C35—C34—C33119.5 (4)
C1—C2—C3121.7 (4)C35—C34—H34120.2
C1—C2—H2119.1C33—C34—H34120.2
C3—C2—H2119.1C36—C35—C34121.3 (5)
C2—C3—C4118.4 (4)C36—C35—H35119.3
C2—C3—C7120.0 (5)C34—C35—H35119.3
C4—C3—C7121.6 (5)C35—C36—C37119.7 (4)
C5—C4—C3121.4 (4)C35—C36—C39120.8 (5)
C5—C4—H4119.3C37—C36—C39119.5 (5)
C3—C4—H4119.3C36—C37—C38120.1 (4)
C4—C5—C6118.8 (4)C36—C37—H37120.0
C4—C5—H5120.6C38—C37—H37120.0
C6—C5—H5120.6C33—C38—C37118.8 (4)
C5—C6—C1121.0 (4)C33—C38—H38120.6
C5—C6—S1120.5 (3)C37—C38—H38120.6
C1—C6—S1118.5 (3)C36—C39—H39A109.5
C3—C7—H7A109.5C36—C39—H39B109.5
C3—C7—H7B109.5H39A—C39—H39B109.5
H7A—C7—H7B109.5C36—C39—H39C109.5
C3—C7—H7C109.5H39A—C39—H39C109.5
H7A—C7—H7C109.5H39B—C39—H39C109.5
H7B—C7—H7C109.5C41—C40—C45119.3 (4)
C9—C8—C13120.7 (3)C41—C40—S6119.0 (3)
C9—C8—O9119.1 (3)C45—C40—S6121.6 (3)
C13—C8—O9120.1 (3)C42—C41—C40119.3 (4)
C10—C9—C8119.6 (3)C42—C41—H41120.4
C10—C9—S2119.0 (3)C40—C41—H41120.4
C8—C9—S2121.3 (3)C41—C42—C43122.1 (3)
C11—C10—C9119.4 (3)C41—C42—Br3119.6 (3)
C11—C10—H10120.3C43—C42—Br3118.2 (3)
C9—C10—H10120.3C42—C43—C44119.3 (4)
C10—C11—C12121.3 (3)C42—C43—H43120.3
C10—C11—Br1118.9 (3)C44—C43—H43120.3
C12—C11—Br1119.7 (3)C43—C44—C45119.2 (3)
C13—C12—C11119.7 (3)C43—C44—S8119.4 (3)
C13—C12—H12120.2C45—C44—S8121.5 (3)
C11—C12—H12120.2C40—C45—C44120.8 (3)
C12—C13—C8119.3 (3)C40—C45—O12119.5 (3)
C12—C13—S8119.0 (3)C44—C45—O12119.6 (3)
C8—C13—S8121.7 (3)C47—C46—C51121.1 (4)
C15—C14—C19118.9 (4)C47—C46—S7119.6 (3)
C15—C14—H14120.5C51—C46—S7119.4 (3)
C19—C14—H14120.5C48—C47—C46119.2 (4)
C14—C15—C16121.1 (4)C48—C47—H47120.4
C14—C15—H15119.4C46—C47—H47120.4
C16—C15—H15119.4C47—C48—C49121.2 (4)
C17—C16—C15118.0 (4)C47—C48—H48119.4
C17—C16—C20122.0 (5)C49—C48—H48119.4
C15—C16—C20120.0 (5)C50—C49—C48118.4 (4)
C18—C17—C16122.3 (4)C50—C49—C52120.6 (4)
C18—C17—H17118.8C48—C49—C52121.0 (4)
C16—C17—H17118.8C51—C50—C49121.9 (4)
C17—C18—C19118.7 (4)C51—C50—H50119.0
C17—C18—H18120.7C49—C50—H50119.0
C19—C18—H18120.7C50—C51—C46118.3 (4)
C14—C19—C18120.9 (4)C50—C51—H51120.9
C14—C19—S3119.3 (3)C46—C51—H51120.9
C18—C19—S3119.7 (3)C49—C52—H52A109.5
C16—C20—H20A109.5C49—C52—H52B109.5
C16—C20—H20B109.5H52A—C52—H52B109.5
H20A—C20—H20B109.5C49—C52—H52C109.5
C16—C20—H20C109.5H52A—C52—H52C109.5
H20A—C20—H20C109.5H52B—C52—H52C109.5
H20B—C20—H20C109.5Cl2—C53—Cl1113.0 (3)
C22—C21—C26121.0 (3)Cl2—C53—H53A109.0
C22—C21—O11119.5 (3)Cl1—C53—H53A109.0
C26—C21—O11119.4 (3)Cl2—C53—H53B109.0
C23—C22—C21119.0 (3)Cl1—C53—H53B109.0
C23—C22—S2119.2 (3)H53A—C53—H53B107.8
C21—C22—S2121.8 (3)C8—O9—S1118.8 (2)
C24—C23—C22119.6 (3)C32—O10—S5117.8 (2)
C24—C23—H23120.2C21—O11—S3119.2 (2)
C22—C23—H23120.2C45—O12—S7119.2 (2)
C23—C24—C25121.7 (3)O1—S1—O2120.9 (2)
C23—C24—Br4119.2 (3)O1—S1—O9107.33 (15)
C25—C24—Br4119.0 (3)O2—S1—O9106.71 (17)
C26—C25—C24119.0 (3)O1—S1—C6111.5 (2)
C26—C25—H25120.5O2—S1—C6107.20 (19)
C24—C25—H25120.5O9—S1—C6101.25 (15)
C25—C26—C21119.6 (3)C9—S2—C2299.98 (16)
C25—C26—S4118.6 (3)O5—S3—O6120.6 (2)
C21—C26—S4121.8 (3)O5—S3—O11107.63 (15)
C28—C27—C32119.7 (3)O6—S3—O11106.77 (17)
C28—C27—S4118.6 (3)O5—S3—C19111.19 (18)
C32—C27—S4121.7 (3)O6—S3—C19107.50 (18)
C29—C28—C27118.9 (3)O11—S3—C19101.35 (15)
C29—C28—H28120.5C27—S4—C2697.10 (15)
C27—C28—H28120.5O4—S5—O3121.12 (18)
C30—C29—C28121.9 (3)O4—S5—O10106.07 (15)
C30—C29—Br2119.5 (3)O3—S5—O10106.85 (14)
C28—C29—Br2118.5 (3)O4—S5—C33107.62 (17)
C29—C30—C31119.6 (3)O3—S5—C33111.79 (19)
C29—C30—H30120.2O10—S5—C33101.43 (15)
C31—C30—H30120.2C31—S6—C4099.90 (17)
C32—C31—C30119.0 (3)O7—S7—O8120.84 (18)
C32—C31—S6121.9 (3)O7—S7—O12107.23 (14)
C30—C31—S6119.1 (3)O8—S7—O12106.70 (15)
C31—C32—C27120.8 (3)O7—S7—C46111.01 (18)
C31—C32—O10119.2 (3)O8—S7—C46108.04 (17)
C27—C32—O10119.9 (3)O12—S7—C46101.15 (15)
C34—C33—C38120.6 (4)C13—S8—C4498.43 (16)
C6—C1—C2—C3−0.1 (6)C41—C42—C43—C44−2.5 (6)
C1—C2—C3—C4−0.8 (7)Br3—C42—C43—C44−179.8 (3)
C1—C2—C3—C7178.1 (4)C42—C43—C44—C450.3 (5)
C2—C3—C4—C50.9 (7)C42—C43—C44—S8179.0 (3)
C7—C3—C4—C5−178.0 (4)C41—C40—C45—C44−2.1 (5)
C3—C4—C5—C6−0.1 (6)S6—C40—C45—C44179.6 (3)
C4—C5—C6—C1−0.9 (6)C41—C40—C45—O12−179.2 (3)
C4—C5—C6—S1178.4 (3)S6—C40—C45—O122.5 (4)
C2—C1—C6—C51.0 (6)C43—C44—C45—C402.0 (5)
C2—C1—C6—S1−178.3 (3)S8—C44—C45—C40−176.7 (3)
C13—C8—C9—C10−1.2 (5)C43—C44—C45—O12179.1 (3)
O9—C8—C9—C10−177.1 (3)S8—C44—C45—O120.4 (5)
C13—C8—C9—S2179.6 (3)C51—C46—C47—C48−0.9 (6)
O9—C8—C9—S23.6 (4)S7—C46—C47—C48178.2 (3)
C8—C9—C10—C11−0.1 (5)C46—C47—C48—C49−0.3 (6)
S2—C9—C10—C11179.2 (3)C47—C48—C49—C501.0 (6)
C9—C10—C11—C120.8 (5)C47—C48—C49—C52−179.0 (4)
C9—C10—C11—Br1176.6 (3)C48—C49—C50—C51−0.6 (6)
C10—C11—C12—C13−0.3 (5)C52—C49—C50—C51179.4 (4)
Br1—C11—C12—C13−176.0 (3)C49—C50—C51—C46−0.5 (6)
C11—C12—C13—C8−1.0 (5)C47—C46—C51—C501.3 (6)
C11—C12—C13—S8178.2 (3)S7—C46—C51—C50−177.8 (3)
C9—C8—C13—C121.7 (5)C9—C8—O9—S1−99.3 (3)
O9—C8—C13—C12177.6 (3)C13—C8—O9—S184.7 (4)
C9—C8—C13—S8−177.4 (3)C31—C32—O10—S5−99.5 (3)
O9—C8—C13—S8−1.5 (4)C27—C32—O10—S583.7 (3)
C19—C14—C15—C16−2.7 (6)C22—C21—O11—S3−97.4 (3)
C14—C15—C16—C172.6 (6)C26—C21—O11—S387.3 (3)
C14—C15—C16—C20−177.3 (4)C40—C45—O12—S7−100.4 (3)
C15—C16—C17—C18−1.1 (6)C44—C45—O12—S782.5 (4)
C20—C16—C17—C18178.8 (4)C8—O9—S1—O119.2 (3)
C16—C17—C18—C19−0.3 (6)C8—O9—S1—O2−111.8 (3)
C15—C14—C19—C181.2 (5)C8—O9—S1—C6136.2 (3)
C15—C14—C19—S3−177.2 (3)C5—C6—S1—O119.2 (4)
C17—C18—C19—C140.3 (6)C1—C6—S1—O1−161.5 (3)
C17—C18—C19—S3178.7 (3)C5—C6—S1—O2153.7 (3)
C26—C21—C22—C23−4.1 (5)C1—C6—S1—O2−27.0 (4)
O11—C21—C22—C23−179.3 (3)C5—C6—S1—O9−94.7 (3)
C26—C21—C22—S2177.9 (2)C1—C6—S1—O984.6 (3)
O11—C21—C22—S22.7 (4)C10—C9—S2—C22109.5 (3)
C21—C22—C23—C241.3 (5)C8—C9—S2—C22−71.2 (3)
S2—C22—C23—C24179.4 (3)C23—C22—S2—C9109.9 (3)
C22—C23—C24—C251.5 (6)C21—C22—S2—C9−72.1 (3)
C22—C23—C24—Br4178.7 (3)C21—O11—S3—O518.4 (3)
C23—C24—C25—C26−1.6 (6)C21—O11—S3—O6−112.4 (3)
Br4—C24—C25—C26−178.8 (3)C21—O11—S3—C19135.2 (3)
C24—C25—C26—C21−1.2 (5)C14—C19—S3—O510.2 (3)
C24—C25—C26—S4179.5 (3)C18—C19—S3—O5−168.2 (3)
C22—C21—C26—C254.0 (5)C14—C19—S3—O6144.2 (3)
O11—C21—C26—C25179.2 (3)C18—C19—S3—O6−34.2 (4)
C22—C21—C26—S4−176.7 (3)C14—C19—S3—O11−103.9 (3)
O11—C21—C26—S4−1.4 (4)C18—C19—S3—O1177.7 (3)
C32—C27—C28—C29−0.3 (5)C28—C27—S4—C26−110.9 (3)
S4—C27—C28—C29−179.4 (3)C32—C27—S4—C2669.9 (3)
C27—C28—C29—C30−1.5 (5)C25—C26—S4—C27−111.9 (3)
C27—C28—C29—Br2−178.2 (3)C21—C26—S4—C2768.8 (3)
C28—C29—C30—C310.6 (6)C32—O10—S5—O4−118.6 (2)
Br2—C29—C30—C31177.3 (3)C32—O10—S5—O311.9 (3)
C29—C30—C31—C322.1 (5)C32—O10—S5—C33129.1 (2)
C29—C30—C31—S6179.8 (3)C34—C33—S5—O4−28.7 (4)
C30—C31—C32—C27−3.8 (5)C38—C33—S5—O4150.4 (3)
S6—C31—C32—C27178.5 (3)C34—C33—S5—O3−164.0 (3)
C30—C31—C32—O10179.4 (3)C38—C33—S5—O315.1 (4)
S6—C31—C32—O101.7 (4)C34—C33—S5—O1082.5 (3)
C28—C27—C32—C313.0 (5)C38—C33—S5—O10−98.4 (3)
S4—C27—C32—C31−177.9 (3)C32—C31—S6—C40−71.4 (3)
C28—C27—C32—O10179.7 (3)C30—C31—S6—C40110.9 (3)
S4—C27—C32—O10−1.2 (4)C41—C40—S6—C31110.3 (3)
C38—C33—C34—C351.6 (6)C45—C40—S6—C31−71.5 (3)
S5—C33—C34—C35−179.3 (3)C45—O12—S7—O713.5 (3)
C33—C34—C35—C36−0.5 (7)C45—O12—S7—O8−117.3 (3)
C34—C35—C36—C37−1.1 (7)C45—O12—S7—C46129.9 (3)
C34—C35—C36—C39179.2 (4)C47—C46—S7—O7−162.0 (3)
C35—C36—C37—C381.7 (7)C51—C46—S7—O717.1 (4)
C39—C36—C37—C38−178.6 (4)C47—C46—S7—O8−27.4 (3)
C34—C33—C38—C37−1.0 (6)C51—C46—S7—O8151.7 (3)
S5—C33—C38—C37179.9 (3)C47—C46—S7—O1284.5 (3)
C36—C37—C38—C33−0.6 (6)C51—C46—S7—O12−96.4 (3)
C45—C40—C41—C42−0.1 (5)C12—C13—S8—C44−110.6 (3)
S6—C40—C41—C42178.2 (3)C8—C13—S8—C4468.6 (3)
C40—C41—C42—C432.4 (6)C43—C44—S8—C13−112.0 (3)
C40—C41—C42—Br3179.7 (3)C45—C44—S8—C1366.6 (3)
Cg1, Cg2, Cg3 and Cg4 are the centroids of the C14–C19, C1–C6, C51–C56 and C33–C38 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C12—H12···O80.952.513.303 (5)141
C53—H53A···O5i0.992.383.175 (5)137
C53—H53B···O4ii0.992.373.249 (5)147
C17—H17···O2iii0.952.383.266 (5)155
C10—H10···Cg10.952.753.698 (1)178
C23—H23···Cg20.952.653.602 (1)176
C30—H30···Cg30.952.803.742 (1)174
C41—H41···Cg40.952.853.794 (1)172
Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the C14–C19, C1–C6, C51–C56 and C33–C38 rings, respectively.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C12—H12⋯O80.952.513.303 (5)141
C53—H53A⋯O5i0.992.383.175 (5)137
C53—H53B⋯O4ii0.992.373.249 (5)147
C17—H17⋯O2iii0.952.383.266 (5)155
C10—H10⋯Cg10.952.753.698 (1)178
C23—H23⋯Cg20.952.653.602 (1)176
C30—H30⋯Cg30.952.803.742 (1)174
C41—H41⋯Cg40.952.853.794 (1)172

Symmetry codes: (i) ; (ii) ; (iii) .

  4 in total

1.  Thiacalixarenes.

Authors:  Naoya Morohashi; Fumitaka Narumi; Nobuhiko Iki; Tetsutaro Hattori; Sotaro Miyano
Journal:  Chem Rev       Date:  2006-12       Impact factor: 60.622

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  Halogen bonding: a paradigm in supramolecular chemistry.

Authors:  P Metrangolo; G Resnati
Journal:  Chemistry       Date:  2001-06-18       Impact factor: 5.236

4.  1,3-alternate and partial cone conformers of tetramethyl (5,11,17,23-tetra-tert-butyl-2,8,14,20-tetrathiacalix[4]arene-25,26,27,28-tetrayltetraoxy)tetraacetate and tetramethyl (5,11,17,23-tetrabromo-2,8,14,20-tetrathiacalix[4]arene-25,26,27,28-tetrayltetraoxy)tetraacetate.

Authors:  Wei-Na Xu; Jiu-Mao Yuan; Yang Liu; Jian-Ping Ma; Dian-Shun Guo
Journal:  Acta Crystallogr C       Date:  2008-05-28       Impact factor: 1.172
  4 in total
  2 in total

1.  5,17-Dibromo-26,28-dihy-droxy-25,27-diprop-oxy-2,8,14,20-tetra-thia-calix[4]arene.

Authors:  Ling-Ling Liu; Lu-Sheng Chen; Jian-Ping Ma; Dian-Shun Guo
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-04-13

2.  5,17-Dibromo-26,28-bis-[(meth-oxy-carbon-yl)meth-oxy]-25,27-diprop-oxy-2,8,14,20-tetra-thia-calix[4]arene.

Authors:  Li-Jing Zhang; Ling-Ling Liu; Qi-Kui Liu; Dian-Shun Guo
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-04-13
  2 in total

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