Regioselective S<sub>N</sub>Ar reaction of the phenoxathiin-based thiacalixarene as a route to a novel macrocyclic skeleton.
Landovský, Tomáš; Eigner, Václav; Babor, Martin; Tichotová, Markéta; Dvořáková, Hana; Lhoták, Pavel; Chemical communications (Cambridge, England) 56 (2019) 78–81; doi:10.1039/c9cc08335a

data_7124542
_publ_section_title
;
 Regioselective S<sub>N</sub>Ar reaction of the phenoxathiin-based
 thiacalixarene as a route to a novel macrocyclic skeleton.
;
_journal_issue                   1
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              78
_journal_page_last               81
_journal_paper_doi               10.1039/c9cc08335a
_journal_volume                  56
_journal_year                    2019
_chemical_formula_moiety         'C45 H58 O13 S4, 0.081(O)'
_chemical_formula_sum            'C45 H58 O13.08 S4'
_chemical_formula_weight         936.50
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2019-09-23 deposited with the CCDC.	2019-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   39.4032(8)
_cell_length_b                   10.2963(2)
_cell_length_c                   23.4609(5)
_cell_measurement_reflns_used    122
_cell_measurement_temperature    180
_cell_measurement_theta_max      67
_cell_measurement_theta_min      4
_cell_volume                     9518.3(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.029
_diffrn_reflns_limit_h_max       47
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            119720
_diffrn_reflns_theta_full        68.336
_diffrn_reflns_theta_max         68.336
_diffrn_reflns_theta_min         2.242
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.348
_exptl_absorpt_correction_T_max  0.80
_exptl_absorpt_correction_T_min  0.62
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             3973.168
_exptl_crystal_size_max          0.366
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.094
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.41
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9984
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     639
_refine_ls_number_reflns         8730
_refine_ls_number_restraints     88
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.0121479
_refine_ls_shift/su_mean         0.0004203
_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: 
 2.73 3.61 1.03 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0959
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.0959
_reflns_limit_h_max              47
_reflns_limit_h_min              0
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              28
_reflns_limit_l_min              0
_reflns_number_gt                8578
_reflns_number_total             8733
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.68
_oxford_diffrn_Wilson_scale      152.60
_oxford_refine_ls_r_factor_ref   0.0465
_oxford_refine_ls_scale          0.077153(12)
_oxford_reflns_number_all        8732
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            c9cc08335a2.cif
_cod_data_source_block           7a
_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/rss-feeds/RSC/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 

 Adding full bibliography for 7124541--7124542.cif.
;
_cod_original_sg_symbol_Hall     '-P 2n 2ab '
_cod_original_sg_symbol_H-M      'P b c n '
_cod_database_code               7124542
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE C(1, X'S, U'S) UNTIL C(162) 
CONTINUE O(1, X'S, U'S, OCC) 
EQUIVALENCE PART(1001, OCC) PART(1002, OCC) 
EQUIVALENCE PART(2001, OCC) PART(2002, OCC) 
WEIGHT -1 PART(1002, OCC) 
WEIGHT -1 PART(2002, OCC) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  30,X'S) H   ( 302,X'S) H   ( 301,X'S) H   ( 303,X'S) 
RIDE C   (  32,X'S) H   ( 323,X'S) H   ( 321,X'S) H   ( 322,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) H   ( 343,X'S) H   ( 342,X'S) 
RIDE C   (  36,X'S) H   ( 362,X'S) H   ( 361,X'S) H   ( 363,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) H   ( 383,X'S) H   ( 382,X'S) 
RIDE C   (  48,X'S) H   ( 482,X'S) H   ( 481,X'S) H   ( 483,X'S) 
RIDE C   (  49,X'S) H   ( 492,X'S) H   ( 493,X'S) H   ( 491,X'S) 
RIDE C   (  50,X'S) H   ( 501,X'S) H   ( 503,X'S) H   ( 502,X'S) 
RIDE C   (  52,X'S) H   ( 522,X'S) H   ( 521,X'S) H   ( 523,X'S) 
RIDE C   (  53,X'S) H   ( 532,X'S) H   ( 533,X'S) H   ( 531,X'S) 
RIDE C   (  54,X'S) H   ( 541,X'S) H   ( 542,X'S) H   ( 543,X'S) 
RIDE C   (  56,X'S) H   ( 562,X'S) H   ( 563,X'S) H   ( 561,X'S) 
RIDE C   (  57,X'S) H   ( 573,X'S) H   ( 571,X'S) H   ( 572,X'S) 
RIDE C   (  58,X'S) H   ( 581,X'S) H   ( 582,X'S) H   ( 583,X'S) 
RIDE C   ( 156,X'S) H   (1562,X'S) H   (1563,X'S) H   (1561,X'S) 
RIDE C   ( 157,X'S) H   (1573,X'S) H   (1571,X'S) H   (1572,X'S) 
RIDE C   ( 158,X'S) H   (1581,X'S) H   (1582,X'S) H   (1583,X'S) 
RIDE C   (  60,X'S) H   ( 603,X'S) H   ( 601,X'S) H   ( 602,X'S) 
RIDE C   (  61,X'S) H   ( 611,X'S) H   ( 613,X'S) H   ( 612,X'S) 
RIDE C   (  62,X'S) H   ( 622,X'S) H   ( 621,X'S) H   ( 623,X'S) 
RIDE C   ( 160,X'S) H   (1603,X'S) H   (1601,X'S) H   (1602,X'S) 
RIDE C   ( 161,X'S) H   (1611,X'S) H   (1613,X'S) H   (1612,X'S) 
RIDE C   ( 162,X'S) H   (1622,X'S) H   (1621,X'S) H   (1623,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 , 0.050000 = C(16) TO C(55) 
DISTANCE 1.540000 , 0.050000 = C(55) TO C(56) 
DISTANCE 1.540000 , 0.050000 = C(55) TO C(57) 
DISTANCE 1.540000 , 0.050000 = C(55) TO C(58) 
ANGLE 109.000000 , 1.000000 = C(16) TO C(55) TO C(56) 
ANGLE 109.000000 , 1.000000 = C(16) TO C(55) TO C(57) 
ANGLE 109.000000 , 1.000000 = C(16) TO C(55) TO C(58) 
ANGLE 109.000000 , 1.000000 = C(56) TO C(55) TO C(57) 
ANGLE 109.000000 , 1.000000 = C(57) TO C(55) TO C(58) 
ANGLE 109.000000 , 1.000000 = C(58) TO C(55) TO C(56) 
DISTANCE 1.540000 , 0.050000 = C(16) TO C(155) 
DISTANCE 1.540000 , 0.050000 = C(155) TO C(156) 
DISTANCE 1.540000 , 0.050000 = C(155) TO C(157) 
DISTANCE 1.540000 , 0.050000 = C(155) TO C(158) 
ANGLE 109.000000 , 1.000000 = C(16) TO C(155) TO C(156) 
ANGLE 109.000000 , 1.000000 = C(16) TO C(155) TO C(157) 
ANGLE 109.000000 , 1.000000 = C(16) TO C(155) TO C(158) 
ANGLE 109.000000 , 1.000000 = C(156) TO C(155) TO C(157) 
ANGLE 109.000000 , 1.000000 = C(157) TO C(155) TO C(158) 
ANGLE 109.000000 , 1.000000 = C(158) TO C(155) TO C(156) 
U(IJ)'S  0.0, 0.001000 = C(55) TO C(155) 
U(IJ)'S  0.0, 0.001000 = C(56) TO C(156) 
U(IJ)'S  0.0, 0.020000 = C(57) TO C(157) 
U(IJ)'S  0.0, 0.001000 = C(58) TO C(158) 
DISTANCE 1.540000 , 0.050000 = C(22) TO C(59) 
DISTANCE 1.540000 , 0.050000 = C(59) TO C(60) 
DISTANCE 1.540000 , 0.050000 = C(59) TO C(61) 
DISTANCE 1.540000 , 0.050000 = C(59) TO C(62) 
ANGLE 109.000000 , 1.000000 = C(22) TO C(59) TO C(60) 
ANGLE 109.000000 , 1.000000 = C(22) TO C(59) TO C(61) 
ANGLE 109.000000 , 1.000000 = C(22) TO C(59) TO C(62) 
ANGLE 109.000000 , 1.000000 = C(60) TO C(59) TO C(61) 
ANGLE 109.000000 , 1.000000 = C(61) TO C(59) TO C(62) 
ANGLE 109.000000 , 1.000000 = C(62) TO C(59) TO C(60) 
DISTANCE 1.540000 , 0.050000 = C(22) TO C(159) 
DISTANCE 1.540000 , 0.050000 = C(159) TO C(160) 
DISTANCE 1.540000 , 0.050000 = C(159) TO C(161) 
DISTANCE 1.540000 , 0.050000 = C(159) TO C(162) 
ANGLE 109.000000 , 1.000000 = C(22) TO C(159) TO C(160) 
ANGLE 109.000000 , 1.000000 = C(22) TO C(159) TO C(161) 
ANGLE 109.000000 , 1.000000 = C(22) TO C(159) TO C(162) 
ANGLE 109.000000 , 1.000000 = C(160) TO C(159) TO C(161) 
ANGLE 109.000000 , 1.000000 = C(161) TO C(159) TO C(162) 
ANGLE 109.000000 , 1.000000 = C(162) TO C(159) TO C(160) 
U(IJ)'S  0.0, 0.001000 = C(59) TO C(159) 
U(IJ)'S  0.0, 0.010000 = C(60) TO C(160) 
U(IJ)'S  0.0, 0.001000 = C(61) TO C(161) 
U(IJ)'S  0.0, 0.001000 = C(62) TO C(162) 
END                                                                             
;