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_1513526
_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         'C40 H46 Cl2 Hg2 O4, C H2 Cl2'
_chemical_formula_sum            'C41 H48 Cl4 Hg2 O4'
_chemical_formula_weight         1147.82
_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                102.480(2)
_cell_angle_beta                 106.494(2)
_cell_angle_gamma                107.577(2)
_cell_formula_units_Z            4
_cell_length_a                   13.3097(3)
_cell_length_b                   16.7693(5)
_cell_length_c                   21.3618(6)
_cell_measurement_reflns_used    13997
_cell_measurement_temperature    120
_cell_measurement_theta_max      67
_cell_measurement_theta_min      3
_cell_volume                     4113.7(2)
_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    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_pressure         101
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.973
_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  0.040
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28548
_diffrn_reflns_theta_full        66.7
_diffrn_reflns_theta_max         67.144
_diffrn_reflns_theta_min         2.928
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    15.897
_exptl_absorpt_correction_T_max  0.53
_exptl_absorpt_correction_T_min  0.08
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.853
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plane
_exptl_crystal_F_000             2216
_exptl_crystal_size_max          0.546
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.040
_refine_diff_density_max         3.40
_refine_diff_density_min         -2.00
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0438
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     973
_refine_ls_number_reflns         14305
_refine_ls_number_restraints     68
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.0011749
_refine_ls_shift/su_mean         0.0000646
_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: 
 0.368E+04 0.615E+04 0.395E+04 0.175E+04 409. 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1641
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1641
_reflns_limit_h_max              14
_reflns_limit_h_min              -15
_reflns_limit_k_max              19
_reflns_limit_k_min              -19
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                11891
_reflns_number_total             14305
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.72
_oxford_diffrn_Wilson_scale      0.55
_oxford_refine_ls_r_factor_ref   0.0563
_oxford_refine_ls_scale          1.426(6)
_oxford_reflns_number_all        14305
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_cod_data_source_file            ol403133b_si_002.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               1513526
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   5,X'S) H   (  51,X'S) H   (  52,X'S) 
RIDE C   (   9,X'S) H   (  92,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 102,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) H   ( 113,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) H   ( 162,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) H   ( 292,X'S) 
RIDE C   (  33,X'S) H   ( 332,X'S) H   ( 331,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) H   ( 353,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) H   ( 372,X'S) 
RIDE C   (  41,X'S) H   ( 411,X'S) H   ( 412,X'S) 
RIDE C   (  42,X'S) H   ( 422,X'S) H   ( 421,X'S) 
RIDE C   (  43,X'S) H   ( 431,X'S) H   ( 433,X'S) H   ( 432,X'S) 
RIDE C   (  44,X'S) H   ( 441,X'S) 
RIDE C   (  45,X'S) H   ( 451,X'S) 
RIDE C   (  46,X'S) H   ( 461,X'S) 
RIDE C   (  47,X'S) H   ( 471,X'S) 
RIDE C   (  48,X'S) H   ( 481,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) 
RIDE C   (  53,X'S) H   ( 531,X'S) 
RIDE C   (  55,X'S) H   ( 551,X'S) H   ( 552,X'S) 
RIDE C   (  59,X'S) H   ( 591,X'S) H   ( 592,X'S) 
RIDE C   (  60,X'S) H   ( 602,X'S) H   ( 601,X'S) 
RIDE C   (  61,X'S) H   ( 611,X'S) H   ( 613,X'S) H   ( 612,X'S) 
RIDE C   (  63,X'S) H   ( 631,X'S) H   ( 632,X'S) 
RIDE C   (  65,X'S) H   ( 651,X'S) 
RIDE C   (  69,X'S) H   ( 691,X'S) 
RIDE C   (  76,X'S) H   ( 761,X'S) H   ( 762,X'S) 
RIDE C   (  80,X'S) H   ( 801,X'S) H   ( 802,X'S) 
RIDE C   (  81,X'S) H   ( 811,X'S) H   ( 812,X'S) 
RIDE C   (  82,X'S) H   ( 822,X'S) H   ( 821,X'S) H   ( 823,X'S) 
RIDE C   (  84,X'S) H   ( 841,X'S) 
RIDE C   (  85,X'S) H   ( 851,X'S) 
RIDE C   (  86,X'S) H   ( 861,X'S) 
RIDE C   (  87,X'S) H   ( 872,X'S) H   ( 871,X'S) 
RIDE C   (  91,X'S) H   ( 911,X'S) H   ( 912,X'S) 
RIDE C   (  92,X'S) H   ( 922,X'S) H   ( 921,X'S) 
RIDE C   (  93,X'S) H   ( 931,X'S) H   ( 933,X'S) H   ( 932,X'S) 
RIDE C   (  94,X'S) H   ( 941,X'S) 
RIDE C   (  95,X'S) H   ( 951,X'S) 
RIDE C   (  96,X'S) H   ( 961,X'S) 
RIDE C   (  98,X'S) H   ( 981,X'S) H   ( 982,X'S) 
RIDE C   ( 101,X'S) H   (1011,X'S) H   (1012,X'S) 
RIDE C   ( 201,X'S) H   (2011,X'S) H   (2012,X'S) 
RIDE C   ( 202,X'S) H   (2022,X'S) H   (2021,X'S) 
RIDE C   ( 203,X'S) H   (2031,X'S) H   (2033,X'S) H   (2032,X'S) 
RIDE C   ( 301,X'S) H   (3011,X'S) H   (3012,X'S) 
RIDE C   ( 302,X'S) H   (3021,X'S) H   (3022,X'S) 
RIDE C   ( 303,X'S) H   (3032,X'S) H   (3031,X'S) H   (3033,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   (2132,X'S) H   (2131,X'S) H   (2133,X'S) 
RIDE C   ( 311,X'S) H   (3112,X'S) H   (3111,X'S) 
RIDE C   ( 312,X'S) H   (3121,X'S) H   (3122,X'S) 
RIDE C   ( 313,X'S) H   (3131,X'S) H   (3132,X'S) H   (3133,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) 
DISTANCE 1.460000 , 0.005000 = O(200) TO C(201) 
DISTANCE 1.505000 , 0.005000 = C(201) TO C(202) 
DISTANCE 1.540000 , 0.005000 = C(202) TO C(203) 
DISTANCE 2.400000 , 0.005000 = O(200) TO C(202) 
DISTANCE 2.510000 , 0.005000 = C(201) TO C(203) 
DISTANCE 1.460000 , 0.005000 = O(200) TO C(301) 
DISTANCE 1.505000 , 0.005000 = C(301) TO C(302) 
DISTANCE 1.540000 , 0.005000 = C(302) TO C(303) 
DISTANCE 2.400000 , 0.005000 = O(200) TO C(302) 
DISTANCE 2.510000 , 0.005000 = C(301) TO C(303) 
U(IJ)'S  0.0, 0.010000 = C(201) TO C(301) 
U(IJ)'S  0.0, 0.010000 = C(202) TO C(302) 
U(IJ)'S  0.0, 0.001000 = C(203) TO C(303) 
U(IJ)'S  0.0, 0.010000 = O(200) TO C(203) 
DISTANCE 1.460000 , 0.005000 = O(210) TO C(211) 
DISTANCE 1.505000 , 0.005000 = C(211) TO C(212) 
DISTANCE 1.540000 , 0.005000 = C(212) TO C(213) 
DISTANCE 2.400000 , 0.005000 = O(210) TO C(212) 
DISTANCE 2.510000 , 0.005000 = C(211) TO C(213) 
DISTANCE 1.460000 , 0.005000 = O(210) TO C(311) 
DISTANCE 1.505000 , 0.005000 = C(311) TO C(312) 
DISTANCE 1.540000 , 0.005000 = C(312) TO C(313) 
DISTANCE 2.400000 , 0.005000 = O(210) TO C(312) 
DISTANCE 2.510000 , 0.005000 = C(311) TO C(313) 
U(IJ)'S  0.0, 0.001000 = C(211) TO C(311) 
U(IJ)'S  0.0, 0.001000 = C(212) TO C(312) 
U(IJ)'S  0.0, 0.001000 = C(213) TO C(313) 
U(IJ)'S  0.0, 0.010000 = O(210) TO C(213) 
END                                                                             
;