Chemistry of 2,14-Dithiacalix[4]arene: Alkylation and Conformational Behavior of Peralkylated Products.
Kortus, Daniel; Mikšátko, Jiří; Kundrát, Ondřej; Babor, Martin; Eigner, Václav; Dvořáková, Hana; Lhoták, Pavel; The Journal of organic chemistry 84 (2019) 11572–11580; doi:10.1021/acs.joc.9b01493

data_4034509
_publ_section_title
;
 Chemistry of 2,14-Dithiacalix[4]arene: Alkylation and Conformational
 Behavior of Peralkylated Products.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11572
_journal_page_last               11580
_journal_paper_doi               10.1021/acs.joc.9b01493
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C54 H76 O4 S2'
_chemical_formula_sum            'C54 H76 O4 S2'
_chemical_formula_weight         853.34
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                108.2731(12)
_cell_angle_beta                 93.3489(12)
_cell_angle_gamma                96.5858(13)
_cell_formula_units_Z            2
_cell_length_a                   10.4974(4)
_cell_length_b                   13.0623(5)
_cell_length_c                   19.5386(7)
_cell_measurement_reflns_used    129
_cell_measurement_temperature    180
_cell_measurement_theta_max      68
_cell_measurement_theta_min      2
_cell_volume                     2514.57(16)
_computing_cell_refinement       'Apex3 (Bruker AXS, 2015)'
_computing_data_collection       'Apex3 (Bruker AXS, 2015)'
_computing_data_reduction        'Apex3 (Bruker AXS, 2015)'
_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    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_pressure         101
_diffrn_ambient_temperature      180
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex3'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            68025
_diffrn_reflns_theta_full        68.324
_diffrn_reflns_theta_max         68.324
_diffrn_reflns_theta_min         2.393
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.277
_exptl_absorpt_correction_T_max  0.74
_exptl_absorpt_correction_T_min  0.61
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.127
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             928.012
_exptl_crystal_size_max          0.541
_exptl_crystal_size_mid          0.278
_exptl_crystal_size_min          0.236
_refine_diff_density_max         0.56
_refine_diff_density_min         -0.26
_refine_ls_extinction_coef       200(10)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9554
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     655
_refine_ls_number_reflns         9190
_refine_ls_number_restraints     116
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.0010432
_refine_ls_shift/su_mean         0.0000592
_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: 
 8.69 13.9 7.70 2.96 0.594 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1156
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1156
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              14
_reflns_limit_k_min              -15
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                8925
_reflns_number_total             9210
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.81
_oxford_diffrn_Wilson_scale      26.65
_oxford_refine_ls_r_factor_ref   0.0461
_oxford_refine_ls_scale          0.21372(14)
_oxford_reflns_number_all        9209
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            jo9b01493_si_007.cif
_cod_data_source_block           DK16_f2_1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'Other' was changed to
'other' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4034509
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
EQUIVALENCE PART(1001, OCC) 
EQUIVALENCE PART(1002, OCC) 
EQUIVALENCE PART(2001, OCC) 
EQUIVALENCE PART(2002, OCC) 
EQUIVALENCE PART(3001, OCC) 
EQUIVALENCE PART(3002, OCC) 
EQUIVALENCE PART(4001, OCC) 
EQUIVALENCE PART(4002, OCC) 
RIDE C   ( 102,X'S) H   (1021,X'S) H   (1022,X'S) S(2,X'S) 
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) S(108,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   ( 114,X'S) H   (1141,X'S) H   (1142,X'S) S(14,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   ( 201,X'S) H   ( 202,X'S) S(120,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) H   ( 302,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) H   ( 312,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) H   ( 322,X'S) H   ( 323,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) H   ( 342,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) H   ( 352,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) H   ( 362,X'S) H   ( 363,X'S) 
RIDE C   ( 134,X'S) H   (1341,X'S) H   (1342,X'S) 
RIDE C   ( 135,X'S) H   (1351,X'S) H   (1352,X'S) 
RIDE C   ( 136,X'S) H   (1361,X'S) H   (1362,X'S) H   (1363,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) H   ( 382,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) H   ( 392,X'S) 
RIDE C   (  40,X'S) H   ( 401,X'S) H   ( 402,X'S) H   ( 403,X'S) 
RIDE C   (  42,X'S) H   ( 421,X'S) H   ( 422,X'S) 
RIDE C   (  43,X'S) H   ( 431,X'S) H   ( 432,X'S) 
RIDE C   (  44,X'S) H   ( 441,X'S) H   ( 442,X'S) H   ( 443,X'S) 
RIDE C   (  46,X'S) H   ( 461,X'S) H   ( 462,X'S) H   ( 463,X'S) 
RIDE C   (  47,X'S) H   ( 471,X'S) H   ( 472,X'S) H   ( 473,X'S) 
RIDE C   (  48,X'S) H   ( 481,X'S) H   ( 482,X'S) H   ( 483,X'S) 
RIDE C   ( 146,X'S) H   (1461,X'S) H   (1462,X'S) H   (1463,X'S) 
RIDE C   ( 147,X'S) H   (1471,X'S) H   (1472,X'S) H   (1473,X'S) 
RIDE C   ( 148,X'S) H   (1481,X'S) H   (1482,X'S) H   (1483,X'S) 
RIDE C   (  50,X'S) H   ( 501,X'S) H   ( 502,X'S) H   ( 503,X'S) 
RIDE C   (  51,X'S) H   ( 511,X'S) H   ( 512,X'S) H   ( 513,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) H   ( 522,X'S) H   ( 523,X'S) 
RIDE C   ( 150,X'S) H   (1501,X'S) H   (1502,X'S) H   (1503,X'S) 
RIDE C   ( 151,X'S) H   (1511,X'S) H   (1512,X'S) H   (1513,X'S) 
RIDE C   ( 152,X'S) H   (1521,X'S) H   (1522,X'S) H   (1523,X'S) 
RIDE C   (  54,X'S) H   ( 541,X'S) H   ( 542,X'S) H   ( 543,X'S) 
RIDE C   (  55,X'S) H   ( 551,X'S) H   ( 552,X'S) H   ( 553,X'S) 
RIDE C   (  56,X'S) H   ( 561,X'S) H   ( 562,X'S) H   ( 563,X'S) 
RIDE C   (  58,X'S) H   ( 581,X'S) H   ( 582,X'S) H   ( 583,X'S) 
RIDE C   (  59,X'S) H   ( 591,X'S) H   ( 592,X'S) H   ( 593,X'S) 
RIDE C   (  60,X'S) H   ( 601,X'S) H   ( 602,X'S) H   ( 603,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) 
U(IJ)'S  0.0, 0.000100 = S(2) TO C(102) 
U(IJ)'S  0.0, 0.000100 = C(8) TO S(108) 
U(IJ)'S  0.0, 0.000100 = S(14) TO C(114) 
U(IJ)'S  0.0, 0.000100 = C(20) TO S(120) 
SUM 0.0001 PART(1001, OCC) PART(1002, OCC) 
DISTANCE 1.460000 , 0.005000 = O(33) TO C(34) 
DISTANCE 1.505000 , 0.005000 = C(34) TO C(35) 
DISTANCE 1.540000 , 0.005000 = C(35) TO C(36) 
ANGLE 109.000000 , 1.000000 = O(33) TO C(34) TO C(35) 
ANGLE 109.000000 , 1.000000 = C(34) TO C(35) TO C(36) 
DISTANCE 1.460000 , 0.005000 = O(33) TO C(134) 
DISTANCE 1.505000 , 0.005000 = C(134) TO C(135) 
DISTANCE 1.540000 , 0.005000 = C(135) TO C(136) 
ANGLE 109.000000 , 1.000000 = O(33) TO C(134) TO C(135) 
ANGLE 109.000000 , 1.000000 = C(134) TO C(135) TO C(136) 
U(IJ)'S  0.0, 0.001000 = C(34) TO C(134) 
U(IJ)'S  0.0, 0.001000 = C(35) TO C(135) 
U(IJ)'S  0.0, 0.010000 = C(36) TO C(136) 
SUM 0.0001 PART(2001, OCC) PART(2002, OCC) 
DISTANCE 1.540000 , 0.005000 = C(45) TO C(46) 
DISTANCE 1.540000 , 0.005000 = C(45) TO C(47) 
DISTANCE 1.540000 , 0.005000 = C(45) TO C(48) 
ANGLE 109.000000 , 1.000000 = C(46) TO C(45) TO C(47) 
ANGLE 109.000000 , 1.000000 = C(47) TO C(45) TO C(48) 
ANGLE 109.000000 , 1.000000 = C(48) TO C(45) TO C(46) 
DISTANCE 1.540000 , 0.005000 = C(45) TO C(146) 
DISTANCE 1.540000 , 0.005000 = C(45) TO C(147) 
DISTANCE 1.540000 , 0.005000 = C(45) TO C(148) 
ANGLE 109.000000 , 1.000000 = C(146) TO C(45) TO C(147) 
ANGLE 109.000000 , 1.000000 = C(147) TO C(45) TO C(148) 
ANGLE 109.000000 , 1.000000 = C(148) TO C(45) TO C(146) 
U(IJ)'S  0.0, 0.010000 = C(46) TO C(146) 
U(IJ)'S  0.0, 0.010000 = C(47) TO C(147) 
U(IJ)'S  0.0, 0.010000 = C(48) TO C(148) 
SUM 0.0001 PART(3001, OCC) PART(3002, OCC) 
DISTANCE 1.540000 , 0.005000 = C(49) TO C(50) 
DISTANCE 1.540000 , 0.005000 = C(49) TO C(51) 
DISTANCE 1.540000 , 0.005000 = C(49) TO C(52) 
ANGLE 109.000000 , 1.000000 = C(50) TO C(49) TO C(51) 
ANGLE 109.000000 , 1.000000 = C(51) TO C(49) TO C(52) 
ANGLE 109.000000 , 1.000000 = C(52) TO C(49) TO C(50) 
DISTANCE 1.540000 , 0.005000 = C(49) TO C(150) 
DISTANCE 1.540000 , 0.005000 = C(49) TO C(151) 
DISTANCE 1.540000 , 0.005000 = C(49) TO C(152) 
ANGLE 109.000000 , 1.000000 = C(150) TO C(49) TO C(151) 
ANGLE 109.000000 , 1.000000 = C(151) TO C(49) TO C(152) 
ANGLE 109.000000 , 1.000000 = C(152) TO C(49) TO C(150) 
U(IJ)'S  0.0, 0.010000 = C(50) TO C(150) 
U(IJ)'S  0.0, 0.010000 = C(51) TO C(151) 
U(IJ)'S  0.0, 0.010000 = C(52) TO C(152) 
SUM 0.0001 PART(4001, OCC) PART(4002, OCC) 
END                                                                             
;