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_7122404
_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         'C47 H64 O4, C13 H30 N, 2(C2 H3 N)'
_chemical_formula_sum            'C64 H101 N3 O4'
_chemical_formula_weight         976.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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     dual
_audit_creation_date             2018-06-25
_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                 105.0730(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3846(2)
_cell_length_b                   15.7251(2)
_cell_length_c                   24.2062(3)
_cell_measurement_reflns_used    29219
_cell_measurement_temperature    100.00(18)
_cell_measurement_theta_max      72.2960
_cell_measurement_theta_min      5.0160
_cell_volume                     5654.59(13)
_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      100.00(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0509
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_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    -34.00  54.00   1.00    1.00    --   35.30 -38.00-120.00   88
  2  \w     23.00  89.00   1.00    1.00    --   35.30-125.00 -90.00   66
  3  \w     16.00 104.00   1.00    1.00    --   35.30  38.00  60.00   88
  4  \w     89.00 174.00   1.00    1.00    --  107.39  61.00 120.00   85
  5  \w     41.00 125.00   1.00    1.00    --  107.39 -61.00 120.00   84
  6  \w     81.00 175.00   1.00    1.00    --  107.39  77.00  90.00   94
  7  \w     38.00 109.00   1.00    1.00    --  107.39 -95.00 -30.00   71
  8  \w     39.00 125.00   1.00    1.00    --  107.39 -45.00 -30.00   86
  9  \w     69.00 178.00   1.00    1.00    --  107.39  15.00-150.00  109
 10  \w      9.00 103.00   1.00    1.00    --   35.30  77.00 150.00   94
 11  \w      1.00  74.00   1.00    1.00    --   35.30 -99.00  90.00   73
 12  \w      9.00 103.00   1.00    1.00    --   35.30  77.00-120.00   94
 13  \w     89.00 174.00   1.00    1.00    --  107.39  61.00 -90.00   85
 14  \w     81.00 175.00   1.00    1.00    --  107.39  77.00  30.00   94
 15  \w     38.00 109.00   1.00    1.00    --  107.39 -95.00 120.00   71
 16  \w     90.00 176.00   1.00    1.00    --  107.39  45.00-120.00   86
 17  \w     81.00 175.00   1.00    1.00    --  107.39  77.00  60.00   94
 18  \w     69.00 178.00   1.00    1.00    --  107.39  15.00   0.00  109
 19  \w    -52.00  32.00   1.00    1.00    --  -35.30  57.00  30.00   84
 20  \w     19.00 103.00   1.00    1.00    --   35.30  57.00 -30.00   84
 21  \w    -34.00  54.00   1.00    1.00    --   35.30 -38.00 120.00   88
 22  \w     81.00 123.00   1.00    1.00    --  107.39  77.00-180.00   42
 23  \w     81.00 175.00   1.00    1.00    --  107.39  77.00   0.00   94
 24  \w     38.00 109.00   1.00    1.00    --  107.39 -95.00-120.00   71
;
_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      -0.0132597000
_diffrn_orient_matrix_UB_12      0.0705094000
_diffrn_orient_matrix_UB_13      0.0412679000
_diffrn_orient_matrix_UB_21      -0.0938778000
_diffrn_orient_matrix_UB_22      0.0192746000
_diffrn_orient_matrix_UB_23      -0.0395023000
_diffrn_orient_matrix_UB_31      -0.0420333000
_diffrn_orient_matrix_UB_32      -0.0652248000
_diffrn_orient_matrix_UB_33      0.0328796000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            54073
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.262
_diffrn_reflns_theta_min         3.782
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.534
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62925
_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    1.147
_exptl_crystal_description       block
_exptl_crystal_F_000             2152
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         2.428
_refine_diff_density_min         -1.151
_refine_diff_density_rms         0.123
_refine_ls_extinction_coef       0.0015(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     665
_refine_ls_number_reflns         11067
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0979
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1799P)^2^+9.3471P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2881
_refine_ls_wR_factor_ref         0.2942
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10061
_reflns_number_total             11067
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc05566a2.cif
_cod_data_source_block           rw011720a_100k
_cod_depositor_comments
'Adding full bibliography for 7122403--7122404.cif.'
_cod_database_code               7122404
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'c h n o '
_shelx_estimated_absorpt_t_max   0.948
_shelx_estimated_absorpt_t_min   0.948
_reflns_odcompleteness_completeness 99.90
_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(C0AA) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.005
3.a Secondary CH2 refined with riding coordinates:
 C00B(H00F,H00G), C00D(H00H,H00I), C00E(H00K,H00L), C00G(H00M,H00N), C00H(H00O,
 H00Q), C00K(H00R,H00S), C00L(H00B,H00C), C00M(H00D,H00E), C00V(H00Z,HA),
 C00Z(H00,HB), C015(H01A,H01B), C01B(H2AA,HE), C01F(H01C,H01D)
3.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C00A(H00A), C00J(H00J), C00P(H00P), C00W(H00W), C010(H010),
 C016(H016), C019(H019)
3.c Idealised Me refined as rotating group:
 C00R(H00T,H00U,H00V), C00T(H00X,H00Y,H), C01A(H01,HC,HD), C01C(H3AA,HF,HG),
 C01E(H5AA,HH,HI), C01I(H01E,H01F,H01G), C01K(H01H,H01I,H01J), C01L(H01K,H01L,
 H01M), C01M(H01N,H01O,H01P), C01O(H4AA,HJ,HK), C01P(H01Q,H01R,H01S), C01R(H01T,
 H01U,H01V), C01U(H01W,H01X,H01Y), C01V(H01Z,HL,HM), C2(H2A,H2B,H2C), C3(H3A,
 H3B,H3C), C4(H4A,H4B,H4C), C6(H6A,H6B,H6C), C1(H1A,H1B,H1C), C1AA(H1AA,H1AB,
 H1AC), C0AA(H0AA,H0AB,H0AC)
3.d Idealised tetrahedral OH refined as rotating group:
 O002(H002), O003(H003), O004(H004)
;
_shelx_res_checksum              77924
_olex2_date_sample_data_collection 2017-04-05
_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 1.623
_oxdiff_exptl_absorpt_empirical_full_min 0.613