Intramolecularly Bridged Calix[4]arenes with Pronounced Complexation Ability toward Neutral Compounds.
Slavík, Petr; Eigner, Václav; Lhoták, Pavel; Organic letters 17 (2015) 2788–2791; doi:10.1021/acs.orglett.5b01200

data_1519652
_publ_section_title
;
 Intramolecularly Bridged Calix[4]arenes with Pronounced Complexation
 Ability toward Neutral Compounds.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2788
_journal_page_last               2791
_journal_paper_doi               10.1021/acs.orglett.5b01200
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C45 H56 O5, C2 H3 N'
_chemical_formula_sum            'C47 H59 N O5'
_chemical_formula_weight         717.99
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P -2ac -2n'
_symmetry_space_group_name_H-M   'P n 21 a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   18.4589(2)
_cell_length_b                   58.0060(9)
_cell_length_c                   11.59672(17)
_cell_measurement_reflns_used    27076
_cell_measurement_temperature    180
_cell_measurement_theta_max      76
_cell_measurement_theta_min      4
_cell_volume                     12416.9(3)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (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      180
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -72
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            51154
_diffrn_reflns_theta_full        71.405
_diffrn_reflns_theta_max         75.963
_diffrn_reflns_theta_min         4.446
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.576
_exptl_absorpt_correction_T_max  0.83
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             4656
_exptl_crystal_size_max          0.690
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.320
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.20
_refine_ls_abs_structure_details 'Flack (1983), 5045 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.39(15)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.8818
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1517
_refine_ls_number_reflns         18855
_refine_ls_number_restraints     139
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0507
_refine_ls_shift/su_max          0.0038762
_refine_ls_shift/su_mean         0.0001256
_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: 
 0.121E+04 0.202E+04 0.122E+04 488. 105. 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1289
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1288
_reflns_limit_h_max              23
_reflns_limit_h_min              0
_reflns_limit_k_max              42
_reflns_limit_k_min              -72
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                18006
_reflns_number_total             18918
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.61
_oxford_diffrn_Wilson_scale      0.59
_oxford_refine_ls_r_factor_ref   0.0526
_oxford_refine_ls_scale          1.469(4)
_oxford_reflns_number_all        18857
_oxford_reflns_threshold_expression_ref I>0.0\s(I)
_cod_data_source_file            ol5b01200_si_004.cif
_cod_data_source_block           6b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Other' changed to 'other'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/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 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 1519652--1519654.cif.
;
_cod_original_sg_symbol_H-M      'P n 21 a '
_cod_original_formula_sum        'C47 H59 N1 O5'
_cod_database_code               1519652
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
EQUIVALENCE PART(1001, OCC) PART(1002, OCC) 
WEIGHT -1 PART(1002, OCC) 
EQUIVALENCE PART(2001, OCC) PART(2002, OCC) 
WEIGHT -1 PART(2002, OCC) 
EQUIVALENCE PART(3001, OCC) PART(3002, OCC) 
WEIGHT -1 PART(3002, OCC) 
RIDE C   (   2,X'S) H   (  21,X'S) H   (  22,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   8,X'S) H   (  82,X'S) H   (  81,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  14,X'S) H   ( 142,X'S) H   ( 141,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) 
RIDE C   (  20,X'S) H   ( 202,X'S) H   ( 201,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE O   (  30,X'S) H   ( 301,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) 
RIDE C   (  33,X'S) H   ( 332,X'S) H   ( 331,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   ( 361,X'S) H   ( 362,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) H   ( 372,X'S) 
RIDE C   (  38,X'S) H   ( 382,X'S) H   ( 381,X'S) H   ( 383,X'S) 
RIDE C   (  40,X'S) H   ( 402,X'S) H   ( 401,X'S) 
RIDE C   (  41,X'S) H   ( 411,X'S) H   ( 412,X'S) 
RIDE C   (  42,X'S) H   ( 421,X'S) H   ( 422,X'S) H   ( 423,X'S) 
RIDE C   ( 340,X'S) H   (3401,X'S) H   (3402,X'S) 
RIDE C   ( 341,X'S) H   (3412,X'S) H   (3411,X'S) 
RIDE C   ( 342,X'S) H   (3421,X'S) H   (3423,X'S) H   (3422,X'S) 
RIDE C   (  44,X'S) H   ( 441,X'S) H   ( 442,X'S) 
RIDE C   (  45,X'S) H   ( 452,X'S) H   ( 451,X'S) 
RIDE C   (  46,X'S) H   ( 461,X'S) H   ( 463,X'S) H   ( 462,X'S) 
RIDE C   (  48,X'S) H   ( 481,X'S) H   ( 482,X'S) 
RIDE C   (  49,X'S) H   ( 491,X'S) H   ( 492,X'S) 
RIDE C   (  50,X'S) H   ( 502,X'S) H   ( 501,X'S) H   ( 503,X'S) 
RIDE C   ( 102,X'S) H   (1022,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   ( 108,X'S) H   (1081,X'S) H   (1082,X'S) 
RIDE C   ( 111,X'S) H   (1111,X'S) 
RIDE C   ( 112,X'S) H   (1121,X'S) 
RIDE C   ( 114,X'S) H   (1141,X'S) H   (1142,X'S) 
RIDE C   ( 116,X'S) H   (1161,X'S) 
RIDE C   ( 117,X'S) H   (1171,X'S) 
RIDE C   ( 118,X'S) H   (1181,X'S) 
RIDE C   ( 120,X'S) H   (1201,X'S) H   (1202,X'S) 
RIDE C   ( 122,X'S) H   (1221,X'S) 
RIDE C   ( 123,X'S) H   (1231,X'S) 
RIDE C   ( 124,X'S) H   (1241,X'S) 
RIDE O   ( 130,X'S) H   (1301,X'S) 
RIDE C   ( 131,X'S) H   (1311,X'S) H   (1312,X'S) 
RIDE C   ( 132,X'S) H   (1321,X'S) H   (1322,X'S) 
RIDE C   ( 133,X'S) H   (1332,X'S) H   (1331,X'S) 
RIDE C   ( 134,X'S) H   (1341,X'S) H   (1343,X'S) H   (1342,X'S) 
RIDE C   ( 136,X'S) H   (1361,X'S) H   (1362,X'S) 
RIDE C   ( 137,X'S) H   (1371,X'S) H   (1372,X'S) 
RIDE C   ( 138,X'S) H   (1382,X'S) H   (1381,X'S) H   (1383,X'S) 
RIDE C   ( 436,X'S) H   (4362,X'S) H   (4361,X'S) 
RIDE C   ( 437,X'S) H   (4371,X'S) H   (4372,X'S) 
RIDE C   ( 438,X'S) H   (4381,X'S) H   (4383,X'S) H   (4382,X'S) 
RIDE C   ( 140,X'S) H   (1401,X'S) H   (1402,X'S) 
RIDE C   ( 141,X'S) H   (1411,X'S) H   (1412,X'S) 
RIDE C   ( 142,X'S) H   (1422,X'S) H   (1421,X'S) H   (1423,X'S) 
RIDE C   ( 144,X'S) H   (1442,X'S) H   (1441,X'S) 
RIDE C   ( 145,X'S) H   (1451,X'S) H   (1452,X'S) 
RIDE C   ( 146,X'S) H   (1461,X'S) H   (1462,X'S) H   (1463,X'S) 
RIDE C   ( 444,X'S) H   (4441,X'S) H   (4442,X'S) 
RIDE C   ( 445,X'S) H   (4452,X'S) H   (4451,X'S) 
RIDE C   ( 446,X'S) H   (4461,X'S) H   (4463,X'S) H   (4462,X'S) 
RIDE C   ( 148,X'S) H   (1481,X'S) H   (1482,X'S) 
RIDE C   ( 149,X'S) H   (1491,X'S) H   (1492,X'S) 
RIDE C   ( 150,X'S) H   (1502,X'S) H   (1501,X'S) H   (1503,X'S) 
RIDE C   ( 202,X'S) H   (2022,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   ( 208,X'S) H   (2081,X'S) H   (2082,X'S) 
RIDE C   ( 211,X'S) H   (2111,X'S) 
RIDE C   ( 212,X'S) H   (2121,X'S) 
RIDE C   ( 214,X'S) H   (2141,X'S) H   (2142,X'S) 
RIDE C   ( 216,X'S) H   (2161,X'S) 
RIDE C   ( 217,X'S) H   (2171,X'S) 
RIDE C   ( 218,X'S) H   (2181,X'S) 
RIDE C   ( 220,X'S) H   (2201,X'S) H   (2202,X'S) 
RIDE C   ( 222,X'S) H   (2221,X'S) 
RIDE C   ( 223,X'S) H   (2231,X'S) 
RIDE C   ( 224,X'S) H   (2241,X'S) 
RIDE O   ( 230,X'S) H   (2301,X'S) 
RIDE C   ( 231,X'S) H   (2311,X'S) H   (2312,X'S) 
RIDE C   ( 232,X'S) H   (2322,X'S) H   (2321,X'S) 
RIDE C   ( 233,X'S) H   (2331,X'S) H   (2332,X'S) 
RIDE C   ( 234,X'S) H   (2341,X'S) H   (2342,X'S) H   (2343,X'S) 
RIDE C   ( 236,X'S) H   (2361,X'S) H   (2362,X'S) 
RIDE C   ( 237,X'S) H   (2372,X'S) H   (2371,X'S) 
RIDE C   ( 238,X'S) H   (2381,X'S) H   (2383,X'S) H   (2382,X'S) 
RIDE C   ( 240,X'S) H   (2401,X'S) H   (2402,X'S) 
RIDE C   ( 241,X'S) H   (2411,X'S) H   (2412,X'S) 
RIDE C   ( 242,X'S) H   (2422,X'S) H   (2421,X'S) H   (2423,X'S) 
RIDE C   ( 244,X'S) H   (2442,X'S) H   (2441,X'S) 
RIDE C   ( 245,X'S) H   (2451,X'S) H   (2452,X'S) 
RIDE C   ( 246,X'S) H   (2461,X'S) H   (2462,X'S) H   (2463,X'S) 
RIDE C   ( 248,X'S) H   (2481,X'S) H   (2482,X'S) 
RIDE C   ( 249,X'S) H   (2492,X'S) H   (2491,X'S) 
RIDE C   ( 250,X'S) H   (2501,X'S) H   (2503,X'S) H   (2502,X'S) 
RIDE C   ( 901,X'S) H   (9011,X'S) H   (9013,X'S) H   (9012,X'S) 
RIDE C   ( 904,X'S) H   (9041,X'S) H   (9043,X'S) H   (9042,X'S) 
RIDE C   ( 907,X'S) H   (9071,X'S) H   (9073,X'S) H   (9072,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 1.441000 , 0.005000 = O(39) TO C(40) 
DISTANCE 1.525000 , 0.005000 = C(40) TO C(41) 
DISTANCE 1.539000 , 0.005000 = C(41) TO C(42) 
ANGLE 109.000000 , 0.100000 = O(39) TO C(40) TO C(41) 
ANGLE 109.000000 , 0.100000 = C(40) TO C(41) TO C(42) 
DISTANCE 1.441000 , 0.005000 = O(39) TO C(340) 
DISTANCE 1.525000 , 0.005000 = C(340) TO C(341) 
DISTANCE 1.539000 , 0.005000 = C(341) TO C(342) 
ANGLE 109.000000 , 0.100000 = O(39) TO C(340) TO C(341) 
ANGLE 109.000000 , 0.100000 = C(340) TO C(341) TO C(342) 
U(IJ)'S  0.0, 0.010000 = O(39) TO C(40) 
U(IJ)'S  0.0, 0.010000 = O(39) TO C(41) 
U(IJ)'S  0.0, 0.010000 = O(39) TO C(42) 
U(IJ)'S  0.0, 0.010000 = O(39) TO C(340) 
U(IJ)'S  0.0, 0.010000 = O(39) TO C(341) 
U(IJ)'S  0.0, 0.010000 = O(39) TO C(342) 
DISTANCE 1.441000 , 0.005000 = O(143) TO C(144) 
DISTANCE 1.525000 , 0.005000 = C(144) TO C(145) 
DISTANCE 1.539000 , 0.005000 = C(145) TO C(146) 
ANGLE 109.000000 , 0.100000 = O(143) TO C(144) TO C(145) 
ANGLE 109.000000 , 0.100000 = C(144) TO C(145) TO C(146) 
DISTANCE 1.441000 , 0.005000 = O(143) TO C(444) 
DISTANCE 1.525000 , 0.005000 = C(444) TO C(445) 
DISTANCE 1.539000 , 0.005000 = C(445) TO C(446) 
ANGLE 109.000000 , 0.100000 = O(143) TO C(444) TO C(445) 
ANGLE 109.000000 , 0.100000 = C(444) TO C(445) TO C(446) 
U(IJ)'S  0.0, 0.010000 = O(143) TO C(144) 
U(IJ)'S  0.0, 0.010000 = O(143) TO C(145) 
U(IJ)'S  0.0, 0.010000 = O(143) TO C(146) 
U(IJ)'S  0.0, 0.010000 = O(143) TO C(444) 
U(IJ)'S  0.0, 0.010000 = O(143) TO C(445) 
U(IJ)'S  0.0, 0.010000 = O(143) TO C(446) 
DISTANCE 1.441000 , 0.005000 = O(135) TO C(136) 
DISTANCE 1.525000 , 0.005000 = C(136) TO C(137) 
DISTANCE 1.539000 , 0.005000 = C(137) TO C(138) 
ANGLE 109.000000 , 0.100000 = O(135) TO C(136) TO C(137) 
ANGLE 109.000000 , 0.100000 = C(136) TO C(137) TO C(138) 
DISTANCE 1.441000 , 0.005000 = O(135) TO C(436) 
DISTANCE 1.525000 , 0.005000 = C(436) TO C(437) 
DISTANCE 1.539000 , 0.005000 = C(437) TO C(438) 
ANGLE 109.000000 , 0.100000 = O(135) TO C(436) TO C(437) 
ANGLE 109.000000 , 0.100000 = C(436) TO C(437) TO C(438) 
U(IJ)'S  0.0, 0.010000 = O(135) TO C(136) 
U(IJ)'S  0.0, 0.010000 = O(135) TO C(137) 
U(IJ)'S  0.0, 0.010000 = O(135) TO C(138) 
U(IJ)'S  0.0, 0.010000 = O(135) TO C(436) 
U(IJ)'S  0.0, 0.010000 = O(135) TO C(437) 
U(IJ)'S  0.0, 0.010000 = O(135) TO C(438) 
END                                                                             
;