Selective monoalkylation of p-tert-butylcalix-[4]-arene in a methyl carbonate ionic liquid.
Whiteside, R. E.; Gunaratne, H. Q. Nimal; Muzio, A. F. V.; Nockemann, P.; Chemical communications (Cambridge, England) 54 (2018) 12037–12040; doi:10.1039/c8cc05566a

data_7122403
_publ_section_title
;
 Selective monoalkylation of p-tert-butylcalix-[4]-arene in a methyl
 carbonate ionic liquid.
;
_journal_issue                   85
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              12037
_journal_page_last               12040
_journal_paper_doi               10.1039/c8cc05566a
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C44 H55 O4, C7 H18 N'
_chemical_formula_sum            'C51 H73 N O4'
_chemical_formula_weight         764.10
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-07-10 deposited with the CCDC.
2018-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.4381(2)
_cell_length_b                   15.9969(2)
_cell_length_c                   18.31405(18)
_cell_measurement_reflns_used    23021
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.5020
_cell_measurement_theta_min      4.6200
_cell_volume                     4522.87(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0509
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.928
_diffrn_measured_fraction_theta_max 0.822
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -32.00  62.00   1.00    3.27    --   35.55 -77.00-180.00   94
  2  \w     23.00  89.00   1.00    3.27    --   35.55-125.00  30.00   66
  3  \w     34.00 101.00   1.00    3.27    --   35.55-145.00 170.00   67
  4  \w     41.00 125.00   1.00   13.07    --  107.39 -61.00 150.00   84
  5  \w     37.00 129.00   1.00   13.07    --  107.39 -30.00  30.00   92
  6  \w     38.00 109.00   1.00   13.07    --  107.39 -95.00 -90.00   71
  7  \w     37.00 115.00   1.00   13.07    --  107.39-111.00-180.00   78
  8  \w     69.00 178.00   1.00   13.07    --  107.39  15.00   0.00  109
  9  \w      9.00 103.00   1.00    3.27    --   35.55  77.00 150.00   94
 10  \w      9.00 103.00   1.00    3.27    --   35.55  77.00 -90.00   94
 11  \w     36.00 146.00   1.00   13.07    --  107.39 -15.00-120.00  110
 12  \w     41.00 125.00   1.00   13.07    --  107.39 -61.00 -30.00   84
 13  \w     86.00 177.00   1.00   13.07    --  107.39  30.00-120.00   91
 14  \w     90.00 176.00   1.00   13.07    --  107.39  45.00  60.00   86
 15  \w    -52.00  32.00   1.00    3.27    --  -35.55  57.00 -60.00   84
 16  \w      9.00 103.00   1.00    3.27    --   35.55  77.00  30.00   94
 17  \w     81.00 175.00   1.00   13.07    --  107.39  77.00  90.00   94
 18  \w     81.00 175.00   1.00   13.07    --  107.39  77.00   0.00   94
 19  \w     90.00 176.00   1.00   13.07    --  107.39  45.00 -90.00   86
 20  \w     86.00 177.00   1.00   13.07    --  107.39  30.00-180.00   91
 21  \w   -103.00 -19.00   1.00    3.27    --  -35.55 -57.00 -60.00   84
 22  \w    -52.00  32.00   1.00    3.27    --  -35.55  57.00  60.00   84
 23  \w     38.00  65.00   1.00   13.07    --  107.39 -95.00   0.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0234454000
_diffrn_orient_matrix_UB_12      -0.0179929000
_diffrn_orient_matrix_UB_13      -0.0802635000
_diffrn_orient_matrix_UB_21      -0.0593156000
_diffrn_orient_matrix_UB_22      0.0721182000
_diffrn_orient_matrix_UB_23      -0.0246305000
_diffrn_orient_matrix_UB_31      0.0766538000
_diffrn_orient_matrix_UB_32      0.0613027000
_diffrn_orient_matrix_UB_33      0.0055543000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.928
_diffrn_reflns_Laue_measured_fraction_max 0.822
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            38974
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.817
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         89.137
_diffrn_reflns_theta_min         3.669
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.533
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.122
_exptl_crystal_description       block
_exptl_crystal_F_000             1672
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     506
_refine_ls_number_reflns         8049
_refine_ls_number_restraints     55
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0636
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1329P)^2^+1.4364P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1757
_refine_ls_wR_factor_ref         0.1780
_reflns_Friedel_coverage         0.928
_reflns_Friedel_fraction_full    0.923
_reflns_Friedel_fraction_max     0.812
_reflns_number_gt                7765
_reflns_number_total             8049
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc05566a2.cif
_cod_data_source_block           n2221calix
_cod_depositor_comments
'Adding full bibliography for 7122403--7122404.cif.'
_cod_original_cell_volume        4522.86(9)
_cod_database_code               7122403
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.901
_shelx_estimated_absorpt_t_min   0.901
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O1) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(O4) \\sim
Ueq, Uanis(N1) \\sim Ueq, Uanis(C01A) \\sim Ueq, Uanis(C017) \\sim Ueq,
Uanis(C016) \\sim Ueq, Uanis(C006) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.001
Uanis(O2) = Uanis(O1) = Uanis(O4) = Uanis(O3)
3.a Secondary CH2 refined with riding coordinates:
 C00J(H00C,H00D), C00U(H00E,H00F), C00X(H00L,H00O), C00Y(H00H,H00I), C00Z(H00J,
 H00K), C016(H2AA,HB), C017(H3AA,HC)
3.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00B(H00B), C00G(H00G), C00M(H00M), C00N(H00N),
 C00T(H00T), C010(H010)
3.c Idealised Me refined as rotating group:
 C011(H01A,H01B,H01C), C012(H01D,H01E,H01F), C013(H01G,H01H,H01I), C015(H1AA,H,
 HA), C019(H01J,H01K,H01L), C01A(H4AA,HD,HE), C01B(H01M,H01N,H01O), C01C(H5AA,
 HF,HG), C01D(H01P,H01Q,H01R), C01E(H01S,H01T,H01U), C01F(H01V,H01W,H01X),
 C01G(H6AA,HH,HI), C01H(H01Y,HJ,HK), C01I(H01Z,HL,HM), C01J(H01,HN,HO),
 C01K(H0AA,HP,HQ)
3.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O2(H2), O1(H1)
;
_shelx_res_checksum              49863
_olex2_date_sample_data_collection 2017-05-02
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.306
_oxdiff_exptl_absorpt_empirical_full_min 0.680