2,14-Dithiacalix[4]arene and its homooxa analogues: synthesis and dynamic NMR study of conformational behaviour
Michal Hucko; Hana Dvorakova; Vaclav Eigner; Pavel Lhotak; Chem.Commun. 51 (2015) 7051–; doi:10.1039/C5cc00819K

data_7116974
_publ_section_title
;
 2,14-Dithiacalix[4]arene and its homooxa analogues: synthesis and dynamic
 NMR study of conformational behaviour
;
_journal_name_full               Chem.Commun.
_journal_page_first              7051
_journal_paper_doi               10.1039/C5cc00819K
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration .
_chemical_formula_moiety         'C43 H54 O5 S2'
_chemical_formula_sum            'C43 H54 O5 S2'
_chemical_formula_weight         715.03
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_update_record
;
2014-11-03 deposited with the CCDC.
2015-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.5447(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3707(2)
_cell_length_b                   18.8446(3)
_cell_length_c                   16.9728(3)
_cell_measurement_reflns_used    9921
_cell_measurement_temperature    120
_cell_measurement_theta_max      76
_cell_measurement_theta_min      4
_cell_volume                     4077.62(12)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_pressure         101
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20067
_diffrn_reflns_theta_full        69.050
_diffrn_reflns_theta_max         75.879
_diffrn_reflns_theta_min         4.187
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.507
_exptl_absorpt_correction_T_max  0.83
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.51
_refine_diff_density_min         -0.33
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9644
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     535
_refine_ls_number_reflns         8206
_refine_ls_number_restraints     108
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.0097579
_refine_ls_shift/su_mean         0.0003736
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 559. 848. 410. 97.9 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0979
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.0979
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              22
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                6849
_reflns_number_total             8210
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.49
_oxford_diffrn_Wilson_scale      0.20
_oxford_refine_ls_r_factor_ref   0.0580
_oxford_refine_ls_scale          2.147(8)
_oxford_reflns_number_all        8206
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            c5cc00819k2.cif
_cod_data_source_block           1a
_cod_original_cell_volume        4077.62(11)
_cod_original_sg_symbol_Hall     '-P 2yab '
_cod_original_sg_symbol_H-M      'P 1 21/a 1 '
_cod_database_code               7116974
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
EQUIVALENCE PART(1001, OCC) PART(1002, OCC) 
EQUIVALENCE PART(2001, OCC) PART(2002, OCC) 
EQUIVALENCE PART(3001, OCC) PART(3002, OCC) 
WEIGHT -1 PART(1002, OCC) 
WEIGHT -1 PART(2002, OCC) 
WEIGHT -1 PART(3002, OCC) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  82,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  20,X'S) H   ( 202,X'S) H   ( 201,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 222,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE O   (  31,X'S) H   ( 311,X'S) 
RIDE O   (  32,X'S) H   ( 321,X'S) 
RIDE O   (  33,X'S) H   ( 331,X'S) 
RIDE O   (  34,X'S) H   ( 341,X'S) 
RIDE C   (  36,X'S) H   ( 362,X'S) H   ( 363,X'S) H   ( 361,X'S) 
RIDE C   (  37,X'S) H   ( 373,X'S) H   ( 372,X'S) H   ( 371,X'S) 
RIDE C   (  38,X'S) H   ( 383,X'S) H   ( 381,X'S) H   ( 382,X'S) 
RIDE C   (  40,X'S) H   ( 403,X'S) H   ( 401,X'S) H   ( 402,X'S) 
RIDE C   (  41,X'S) H   ( 412,X'S) H   ( 413,X'S) H   ( 411,X'S) 
RIDE C   (  42,X'S) H   ( 423,X'S) H   ( 422,X'S) H   ( 421,X'S) 
RIDE C   (  44,X'S) H   ( 441,X'S) H   ( 443,X'S) H   ( 442,X'S) 
RIDE C   (  45,X'S) H   ( 451,X'S) H   ( 452,X'S) H   ( 453,X'S) 
RIDE C   (  46,X'S) H   ( 463,X'S) H   ( 461,X'S) H   ( 462,X'S) 
RIDE C   (  48,X'S) H   ( 483,X'S) H   ( 481,X'S) H   ( 482,X'S) 
RIDE C   (  49,X'S) H   ( 491,X'S) H   ( 493,X'S) H   ( 492,X'S) 
RIDE C   (  50,X'S) H   ( 503,X'S) H   ( 501,X'S) H   ( 502,X'S) 
RIDE C   ( 136,X'S) H   (1361,X'S) H   (1363,X'S) H   (1362,X'S) 
RIDE C   ( 137,X'S) H   (1371,X'S) H   (1373,X'S) H   (1372,X'S) 
RIDE C   ( 138,X'S) H   (1382,X'S) H   (1383,X'S) H   (1381,X'S) 
RIDE C   ( 144,X'S) H   (1443,X'S) H   (1441,X'S) H   (1442,X'S) 
RIDE C   ( 145,X'S) H   (1451,X'S) H   (1453,X'S) H   (1452,X'S) 
RIDE C   ( 146,X'S) H   (1461,X'S) H   (1462,X'S) H   (1463,X'S) 
RIDE C   ( 148,X'S) H   (1482,X'S) H   (1483,X'S) H   (1481,X'S) 
RIDE C   ( 149,X'S) H   (1491,X'S) H   (1493,X'S) H   (1492,X'S) 
RIDE C   ( 150,X'S) H   (1502,X'S) H   (1501,X'S) H   (1503,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
DISTANCE 1.540000 , 0.005000 = C(35) TO C(36) 
DISTANCE 1.540000 , 0.005000 = C(35) TO C(37) 
DISTANCE 1.540000 , 0.005000 = C(35) TO C(38) 
ANGLE 109.000000 , 1.000000 = C(36) TO C(35) TO C(37) 
ANGLE 109.000000 , 1.000000 = C(37) TO C(35) TO C(38) 
ANGLE 109.000000 , 1.000000 = C(38) TO C(35) TO C(36) 
DISTANCE 1.540000 , 0.005000 = C(35) TO C(136) 
DISTANCE 1.540000 , 0.005000 = C(35) TO C(137) 
DISTANCE 1.540000 , 0.005000 = C(35) TO C(138) 
ANGLE 109.000000 , 1.000000 = C(136) TO C(35) TO C(137) 
ANGLE 109.000000 , 1.000000 = C(137) TO C(35) TO C(138) 
ANGLE 109.000000 , 1.000000 = C(138) TO C(35) TO C(136) 
U(IJ)'S  0.0, 0.010000 = C(36) TO C(136) 
U(IJ)'S  0.0, 0.010000 = C(37) TO C(137) 
U(IJ)'S  0.0, 0.010000 = C(38) TO C(138) 
DISTANCE 1.540000 , 0.005000 = C(43) TO C(44) 
DISTANCE 1.540000 , 0.005000 = C(43) TO C(45) 
DISTANCE 1.540000 , 0.005000 = C(43) TO C(46) 
ANGLE 109.000000 , 1.000000 = C(44) TO C(43) TO C(45) 
ANGLE 109.000000 , 1.000000 = C(45) TO C(43) TO C(46) 
ANGLE 109.000000 , 1.000000 = C(46) TO C(43) TO C(44) 
DISTANCE 1.540000 , 0.005000 = C(43) TO C(144) 
DISTANCE 1.540000 , 0.005000 = C(43) TO C(145) 
DISTANCE 1.540000 , 0.005000 = C(43) TO C(146) 
ANGLE 109.000000 , 1.000000 = C(144) TO C(43) TO C(145) 
ANGLE 109.000000 , 1.000000 = C(145) TO C(43) TO C(146) 
ANGLE 109.000000 , 1.000000 = C(146) TO C(43) TO C(144) 
U(IJ)'S  0.0, 0.010000 = C(44) TO C(144) 
U(IJ)'S  0.0, 0.010000 = C(45) TO C(145) 
U(IJ)'S  0.0, 0.010000 = C(46) TO C(146) 
DISTANCE 1.540000 , 0.005000 = C(47) TO C(48) 
DISTANCE 1.540000 , 0.005000 = C(47) TO C(49) 
DISTANCE 1.540000 , 0.005000 = C(47) TO C(50) 
ANGLE 109.000000 , 1.000000 = C(48) TO C(47) TO C(49) 
ANGLE 109.000000 , 1.000000 = C(49) TO C(47) TO C(50) 
ANGLE 109.000000 , 1.000000 = C(50) TO C(47) TO C(48) 
DISTANCE 1.540000 , 0.005000 = C(47) TO C(148) 
DISTANCE 1.540000 , 0.005000 = C(47) TO C(149) 
DISTANCE 1.540000 , 0.005000 = C(47) TO C(150) 
ANGLE 109.000000 , 1.000000 = C(148) TO C(47) TO C(149) 
ANGLE 109.000000 , 1.000000 = C(149) TO C(47) TO C(150) 
ANGLE 109.000000 , 1.000000 = C(150) TO C(47) TO C(148) 
U(IJ)'S  0.0, 0.010000 = C(48) TO C(47) 
U(IJ)'S  0.0, 0.010000 = C(49) TO C(47) 
U(IJ)'S  0.0, 0.010000 = C(50) TO C(47) 
U(IJ)'S  0.0, 0.010000 = C(148) TO C(47) 
U(IJ)'S  0.0, 0.010000 = C(149) TO C(47) 
U(IJ)'S  0.0, 0.010000 = C(150) TO C(47) 
END                                                                             
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