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_1513524
_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         'C46 H50 Hg1 I1 N1 O6'
_chemical_formula_sum            'C46 H50 Hg I N O6'
_chemical_formula_weight         1040.40
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 97.8829(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.64125(16)
_cell_length_b                   16.5808(2)
_cell_length_c                   18.5708(3)
_cell_measurement_reflns_used    16156
_cell_measurement_temperature    120
_cell_measurement_theta_max      67
_cell_measurement_theta_min      3
_cell_volume                     4160.70(10)
_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 0.98
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20933
_diffrn_reflns_theta_full        66.82
_diffrn_reflns_theta_max         67.12
_diffrn_reflns_theta_min         3.271
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    12.850
_exptl_absorpt_correction_T_max  0.36
_exptl_absorpt_correction_T_min  0.05
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plane
_exptl_crystal_F_000             2056.001
_exptl_crystal_size_max          0.403
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.080
_refine_diff_density_max         1.71
_refine_diff_density_min         -1.76
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0167
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     631
_refine_ls_number_reflns         7264
_refine_ls_number_restraints     258
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0708
_refine_ls_shift/su_max          0.0076927
_refine_ls_shift/su_mean         0.0002394
_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: 
 0.498E+04 0.702E+04 0.531E+04 0.271E+04 0.113E+04 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1503
_refine_ls_wR_factor_gt          0.1503
_refine_ls_wR_factor_ref         0.1503
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              21
_reflns_limit_l_min              0
_reflns_number_gt                7071
_reflns_number_total             7264
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.17
_oxford_diffrn_Wilson_scale      0.26
_oxford_refine_ls_r_factor_ref   0.0717
_oxford_refine_ls_scale          2.067(15)
_oxford_reflns_number_all        7264
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_cod_data_source_file            ol403133b_si_004.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        4160.69(9)
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_original_formula_sum        'C46 H50 Hg1 I1 N1 O6'
_cod_database_code               1513524
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) H   ( 282,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) H   ( 322,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) H   ( 343,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) H   ( 362,X'S) 
RIDE C   (  40,X'S) H   ( 401,X'S) H   ( 402,X'S) 
RIDE C   (  41,X'S) H   ( 411,X'S) H   ( 412,X'S) 
RIDE C   (  42,X'S) H   ( 423,X'S) H   ( 422,X'S) H   ( 421,X'S) 
RIDE C   (  43,X'S) H   ( 431,X'S) 
RIDE C   (  44,X'S) H   ( 441,X'S) 
RIDE C   (  45,X'S) H   ( 451,X'S) 
RIDE C   ( 101,X'S) H   (1011,X'S) 
RIDE C   ( 102,X'S) H   (1021,X'S) 
RIDE C   ( 104,X'S) H   (1041,X'S) 
RIDE C   ( 105,X'S) H   (1051,X'S) 
RIDE C   ( 201,X'S) H   (2011,X'S) 
RIDE C   ( 202,X'S) H   (2021,X'S) 
RIDE C   ( 204,X'S) H   (2041,X'S) 
RIDE C   ( 205,X'S) H   (2051,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   ( 121,X'S) H   (1211,X'S) H   (1212,X'S) 
RIDE C   ( 122,X'S) H   (1221,X'S) H   (1222,X'S) 
RIDE C   ( 123,X'S) H   (1231,X'S) H   (1232,X'S) H   (1233,X'S) 
RIDE C   ( 221,X'S) H   (2211,X'S) H   (2212,X'S) 
RIDE C   ( 222,X'S) H   (2221,X'S) H   (2222,X'S) 
RIDE C   ( 223,X'S) H   (2231,X'S) H   (2232,X'S) H   (2233,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
DISTANCE 1.390000 , 0.050000 = C(100) TO C(101) 
DISTANCE 1.390000 , 0.050000 = C(101) TO C(102) 
DISTANCE 1.390000 , 0.050000 = C(102) TO C(103) 
DISTANCE 1.390000 , 0.050000 = C(103) TO C(104) 
DISTANCE 1.390000 , 0.050000 = C(104) TO C(105) 
DISTANCE 1.390000 , 0.050000 = C(105) TO C(100) 
ANGLE 120.000000 , 1.000000 = C(100) TO C(101) TO C(102) 
ANGLE 120.000000 , 1.000000 = C(101) TO C(102) TO C(103) 
ANGLE 120.000000 , 1.000000 = C(102) TO C(103) TO C(104) 
ANGLE 120.000000 , 1.000000 = C(103) TO C(104) TO C(105) 
ANGLE 120.000000 , 1.000000 = C(104) TO C(105) TO C(100) 
ANGLE 120.000000 , 1.000000 = C(105) TO C(100) TO C(101) 
DISTANCE 1.420000 , 0.050000 = C(103) TO N(106) 
DISTANCE 1.200000 , 0.050000 = N(106) TO O(107) 
DISTANCE 1.200000 , 0.050000 = N(106) TO O(108) 
ANGLE 120.000000 , 1.000000 = C(102) TO C(103) TO N(106) 
PLANAR 0.010000  C(100) C(101) C(102) C(103) C(104) C(105) C(21) 
DISTANCE 1.390000 , 0.050000 = C(200) TO C(201) 
DISTANCE 1.390000 , 0.050000 = C(201) TO C(202) 
DISTANCE 1.390000 , 0.050000 = C(202) TO C(203) 
DISTANCE 1.390000 , 0.050000 = C(203) TO C(204) 
DISTANCE 1.390000 , 0.050000 = C(204) TO C(205) 
DISTANCE 1.390000 , 0.050000 = C(205) TO C(200) 
ANGLE 120.000000 , 1.000000 = C(200) TO C(201) TO C(202) 
ANGLE 120.000000 , 1.000000 = C(201) TO C(202) TO C(203) 
ANGLE 120.000000 , 1.000000 = C(202) TO C(203) TO C(204) 
ANGLE 120.000000 , 1.000000 = C(203) TO C(204) TO C(205) 
ANGLE 120.000000 , 1.000000 = C(204) TO C(205) TO C(200) 
ANGLE 120.000000 , 1.000000 = C(205) TO C(200) TO C(201) 
DISTANCE 1.420000 , 0.050000 = C(203) TO N(206) 
DISTANCE 1.200000 , 0.050000 = N(206) TO O(207) 
DISTANCE 1.200000 , 0.050000 = N(206) TO O(208) 
ANGLE 120.000000 , 1.000000 = C(202) TO C(203) TO N(206) 
PLANAR 0.010000  C(200) C(201) C(202) C(203) C(204) C(205) C(21) 
U(IJ)'S  0.0, 0.010000 = C(100) TO C(101) 
U(IJ)'S  0.0, 0.010000 = C(101) TO C(102) 
U(IJ)'S  0.0, 0.010000 = C(102) TO C(103) 
U(IJ)'S  0.0, 0.010000 = C(103) TO C(104) 
U(IJ)'S  0.0, 0.010000 = C(104) TO C(105) 
U(IJ)'S  0.0, 0.010000 = C(105) TO C(100) 
U(IJ)'S  0.0, 0.010000 = C(103) TO N(106) 
U(IJ)'S  0.0, 0.010000 = N(106) TO O(107) 
U(IJ)'S  0.0, 0.010000 = N(106) TO O(108) 
U(IJ)'S  0.0, 0.001000 = C(100) TO C(200) 
U(IJ)'S  0.0, 0.001000 = C(101) TO C(201) 
U(IJ)'S  0.0, 0.001000 = C(102) TO C(202) 
U(IJ)'S  0.0, 0.001000 = C(103) TO C(203) 
U(IJ)'S  0.0, 0.001000 = C(104) TO C(204) 
U(IJ)'S  0.0, 0.001000 = C(105) TO C(205) 
U(IJ)'S  0.0, 0.001000 = N(106) TO N(206) 
U(IJ)'S  0.0, 0.001000 = O(107) TO O(207) 
U(IJ)'S  0.0, 0.001000 = O(108) TO O(208) 
DISTANCE 1.460000 , 0.005000 = O(110) TO C(111) 
DISTANCE 1.505000 , 0.005000 = C(111) TO C(112) 
DISTANCE 1.540000 , 0.005000 = C(112) TO C(113) 
ANGLE 109.000000 , 1.000000 = O(110) TO C(111) TO C(112) 
ANGLE 109.000000 , 1.000000 = C(111) TO C(112) TO C(113) 
DISTANCE 1.460000 , 0.005000 = O(110) TO C(211) 
DISTANCE 1.505000 , 0.005000 = C(211) TO C(212) 
DISTANCE 1.540000 , 0.005000 = C(212) TO C(213) 
ANGLE 109.000000 , 1.000000 = O(110) TO C(211) TO C(212) 
ANGLE 109.000000 , 1.000000 = C(211) TO C(212) TO C(213) 
U(IJ)'S  0.0, 0.010000 = O(110) TO C(111) 
U(IJ)'S  0.0, 0.010000 = C(111) TO C(112) 
U(IJ)'S  0.0, 0.010000 = C(112) TO C(113) 
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) 
DISTANCE 1.460000 , 0.005000 = O(120) TO C(121) 
DISTANCE 1.505000 , 0.005000 = C(121) TO C(122) 
DISTANCE 1.540000 , 0.005000 = C(122) TO C(123) 
ANGLE 109.000000 , 1.000000 = O(120) TO C(121) TO C(122) 
ANGLE 109.000000 , 1.000000 = C(121) TO C(122) TO C(123) 
DISTANCE 1.460000 , 0.005000 = O(120) TO C(221) 
DISTANCE 1.505000 , 0.005000 = C(221) TO C(222) 
DISTANCE 1.540000 , 0.005000 = C(222) TO C(223) 
ANGLE 109.000000 , 1.000000 = O(120) TO C(221) TO C(222) 
ANGLE 109.000000 , 1.000000 = C(221) TO C(222) TO C(223) 
U(IJ)'S  0.0, 0.010000 = O(120) TO C(121) 
U(IJ)'S  0.0, 0.010000 = C(121) TO C(122) 
U(IJ)'S  0.0, 0.010000 = C(122) TO C(123) 
U(IJ)'S  0.0, 0.010000 = C(121) TO C(221) 
U(IJ)'S  0.0, 0.010000 = C(122) TO C(222) 
U(IJ)'S  0.0, 0.010000 = C(123) TO C(223) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
U(IJ)'S  0.0, 0.005000 = HG(1) TO C(37) 
U(IJ)'S  0.0, 0.005000 = HG(1) TO C(3) 
END                                                                             
;