Dimercuration of calix[4]arenes: novel substitution pattern in calixarene chemistry.
Flídrová, Karolína; Böhm, Stanislav; Dvořáková, Hana; Eigner, Václav; Lhoták, Pavel; Organic letters 16 (2014) 138–141; doi:10.1021/ol403133b

data_1513525
_publ_section_title
;
 Dimercuration of calix[4]arenes: novel substitution pattern in calixarene
 chemistry.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              138
_journal_page_last               141
_journal_paper_doi               10.1021/ol403133b
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         '2(C40 H46 Cl2 Hg2 O4), 3(C H2 Cl2)'
_chemical_formula_sum            'C83 H98 Cl10 Hg4 O8'
_chemical_formula_weight         2380.58
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                107.832(2)
_cell_angle_beta                 98.237(2)
_cell_angle_gamma                109.345(3)
_cell_formula_units_Z            2
_cell_length_a                   13.5818(4)
_cell_length_b                   17.1690(5)
_cell_length_c                   21.3367(6)
_cell_measurement_reflns_used    14076
_cell_measurement_temperature    120
_cell_measurement_theta_max      28
_cell_measurement_theta_min      3
_cell_volume                     4299.9(3)
_computing_cell_refinement       'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_data_collection       'Gemini, (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED, (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    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_pressure         101
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.831
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.046
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            18224
_diffrn_reflns_theta_full        25.133
_diffrn_reflns_theta_max         28.560
_diffrn_reflns_theta_min         2.887
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.482
_exptl_absorpt_correction_T_max  0.36
_exptl_absorpt_correction_T_min  0.09
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.839
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plane
_exptl_crystal_F_000             2300
_exptl_crystal_size_max          0.851
_exptl_crystal_size_mid          0.366
_exptl_crystal_size_min          0.136
_refine_diff_density_max         4.93
_refine_diff_density_min         -3.71
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0977
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1000
_refine_ls_number_reflns         18224
_refine_ls_number_restraints     116
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.0016858
_refine_ls_shift/su_mean         0.0000534
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.10P)^2^ + 0.00P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1734
_refine_ls_wR_factor_gt          0.1537
_refine_ls_wR_factor_ref         0.1734
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              20
_reflns_limit_k_min              -21
_reflns_limit_l_max              28
_reflns_limit_l_min              0
_reflns_number_gt                12640
_reflns_number_total             18224
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.89
_oxford_diffrn_Wilson_scale      0.44
_oxford_refine_ls_r_factor_ref   0.0908
_oxford_refine_ls_scale          1.553(7)
_oxford_reflns_number_all        18224
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_cod_data_source_file            ol403133b_si_003.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               1513525
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  82,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  92,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) H   ( 162,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) H   ( 183,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) H   ( 292,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) H   ( 332,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) H   ( 342,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) H   ( 362,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) 
RIDE C   (  40,X'S) H   ( 401,X'S) 
RIDE C   (  41,X'S) H   ( 411,X'S) 
RIDE C   (  42,X'S) H   ( 421,X'S) 
RIDE C   (  46,X'S) H   ( 461,X'S) 
RIDE C   (  48,X'S) H   ( 481,X'S) H   ( 482,X'S) 
RIDE C   (  50,X'S) H   ( 501,X'S) 
RIDE C   (  51,X'S) H   ( 511,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) 
RIDE C   (  56,X'S) H   ( 561,X'S) H   ( 562,X'S) 
RIDE C   (  57,X'S) H   ( 571,X'S) H   ( 572,X'S) 
RIDE C   (  62,X'S) H   ( 621,X'S) 
RIDE C   (  63,X'S) H   ( 631,X'S) 
RIDE C   (  67,X'S) H   ( 671,X'S) H   ( 672,X'S) 
RIDE C   (  71,X'S) H   ( 711,X'S) H   ( 712,X'S) 
RIDE C   (  72,X'S) H   ( 721,X'S) H   ( 722,X'S) 
RIDE C   (  73,X'S) H   ( 731,X'S) H   ( 732,X'S) H   ( 733,X'S) 
RIDE C   (  75,X'S) H   ( 751,X'S) H   ( 752,X'S) 
RIDE C   (  79,X'S) H   ( 791,X'S) H   ( 792,X'S) 
RIDE C   (  80,X'S) H   ( 801,X'S) 
RIDE C   (  81,X'S) H   ( 811,X'S) 
RIDE C   (  82,X'S) H   ( 821,X'S) 
RIDE C   (  83,X'S) H   ( 831,X'S) 
RIDE C   (  85,X'S) H   ( 851,X'S) H   ( 852,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) H   (  73,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) H   ( 152,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) H   ( 232,X'S) 
RIDE C   (  70,X'S) H   ( 701,X'S) H   ( 702,X'S) H   ( 703,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) H   ( 242,X'S) H   ( 243,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) H   ( 322,X'S) H   ( 323,X'S) 
RIDE C   ( 101,X'S) H   (1011,X'S) H   (1012,X'S) 
RIDE C   ( 102,X'S) H   (1021,X'S) H   (1022,X'S) 
RIDE C   ( 103,X'S) H   (1031,X'S) H   (1032,X'S) H   (1033,X'S) 
RIDE C   ( 201,X'S) H   (2011,X'S) H   (2012,X'S) 
RIDE C   ( 202,X'S) H   (2021,X'S) H   (2022,X'S) 
RIDE C   ( 203,X'S) H   (2031,X'S) H   (2032,X'S) H   (2033,X'S) 
RIDE C   ( 111,X'S) H   (1111,X'S) H   (1112,X'S) 
RIDE C   ( 112,X'S) H   (1121,X'S) H   (1122,X'S) 
RIDE C   ( 113,X'S) H   (1131,X'S) H   (1132,X'S) H   (1133,X'S) 
RIDE C   ( 211,X'S) H   (2111,X'S) H   (2112,X'S) 
RIDE C   ( 212,X'S) H   (2121,X'S) H   (2122,X'S) 
RIDE C   ( 213,X'S) H   (2131,X'S) H   (2132,X'S) H   (2133,X'S) 
RIDE C   ( 120,X'S) H   (1201,X'S) H   (1202,X'S) 
RIDE C   ( 130,X'S) H   (1301,X'S) H   (1302,X'S) 
END                                                                             
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_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, 0.010000 = C(10) TO C(11) 
U(IJ)'S  0.0, 0.010000 = C(5) TO C(6) 
U(IJ)'S  0.0, 0.010000 = C(12) TO C(13) 
U(IJ)'S  0.0, 0.010000 = O(110) TO C(111) 
U(IJ)'S  0.0, 0.010000 = O(110) TO C(112) 
U(IJ)'S  0.0, 0.010000 = O(110) TO C(113) 
U(IJ)'S  0.0, 0.010000 = O(100) TO C(101) 
U(IJ)'S  0.0, 0.010000 = O(100) TO C(102) 
U(IJ)'S  0.0, 0.010000 = O(100) TO C(103) 
DISTANCE 1.460000 , 0.050000 = O(100) TO C(101) 
DISTANCE 1.505000 , 0.050000 = C(101) TO C(102) 
DISTANCE 1.540000 , 0.050000 = C(102) TO C(103) 
DISTANCE 2.400000 , 0.050000 = O(100) TO C(102) 
DISTANCE 2.510000 , 0.050000 = C(101) TO C(103) 
DISTANCE 1.460000 , 0.050000 = O(100) TO C(201) 
DISTANCE 1.505000 , 0.050000 = C(201) TO C(202) 
DISTANCE 1.540000 , 0.050000 = C(202) TO C(203) 
DISTANCE 2.400000 , 0.050000 = O(100) TO C(202) 
DISTANCE 2.510000 , 0.050000 = C(201) TO C(203) 
U(IJ)'S  0.0, 0.010000 = C(101) TO C(201) 
U(IJ)'S  0.0, 0.010000 = C(102) TO C(202) 
U(IJ)'S  0.0, 0.010000 = C(103) TO C(203) 
DISTANCE 1.460000 , 0.050000 = O(110) TO C(111) 
DISTANCE 1.505000 , 0.050000 = C(111) TO C(112) 
DISTANCE 1.540000 , 0.050000 = C(112) TO C(113) 
DISTANCE 2.400000 , 0.050000 = O(110) TO C(112) 
DISTANCE 2.510000 , 0.050000 = C(111) TO C(113) 
DISTANCE 1.460000 , 0.050000 = O(110) TO C(211) 
DISTANCE 1.505000 , 0.050000 = C(211) TO C(212) 
DISTANCE 1.540000 , 0.050000 = C(212) TO C(213) 
DISTANCE 2.400000 , 0.050000 = O(110) TO C(212) 
DISTANCE 2.510000 , 0.050000 = C(211) TO C(213) 
U(IJ)'S  0.0, 0.010000 = C(111) TO C(211) 
U(IJ)'S  0.0, 0.010000 = C(112) TO C(212) 
U(IJ)'S  0.0, 0.010000 = C(113) TO C(213) 
U(IJ)'S  0.0, 0.010000 = C(6) TO O(7) 
END                                                                             
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