# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_NEW
_database_code_depnum_ccdc_archive 'CCDC 720988'
_audit_update_record             
;
2016-01-16 deposited with the CCDC.
2016-10-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        p-t-butylcalix[4]arene
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C51 H64 O4'
_chemical_formula_weight         741.02

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           85
_space_group_name_H-M_alt        'P 4/n'
_space_group_name_Hall           '-P 4a'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y+1/2, x, z'
'y, -x+1/2, z'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y-1/2, -x, -z'
'-y, x-1/2, -z'

_cell_length_a                   12.754(5)
_cell_length_b                   12.754(5)
_cell_length_c                   13.787(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2243(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3120
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      23.1

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.097
_exptl_crystal_F_000             804
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.067
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed tube'
_diffrn_measurement_device_type  'Bruker axs kapaa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21156
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.175
_diffrn_reflns_theta_max         24.988
_diffrn_reflns_theta_full        24.988
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1990
_reflns_number_gt                1366
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0770P)²+0.6315P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1990
_refine_ls_number_parameters     184
_refine_ls_number_restraints     154
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1722
_refine_ls_wR_factor_gt          0.1381
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.06676(14) 0.15540(14) 0.53904(15) 0.0523(5) Uani 1 1 d . . . . .
C2 C -0.00243(14) 0.22608(14) 0.58073(15) 0.0529(5) Uani 1 1 d . . . . .
C3 C -0.05391(16) 0.19698(17) 0.66429(17) 0.0605(6) Uani 1 1 d . . . . .
C4 C -0.03887(17) 0.10045(17) 0.70837(17) 0.0660(6) Uani 1 1 d D . . . .
C5 C 0.03135(16) 0.03273(16) 0.66391(17) 0.0626(6) Uani 1 1 d . . . . .
H5 H 0.0425 -0.0328 0.6917 0.075 Uiso 1 1 calc R U . . .
C6 C 0.08531(14) 0.05771(14) 0.58078(16) 0.0541(5) Uani 1 1 d . . . . .
C7 C -0.1047(9) 0.0541(9) 0.7917(8) 0.076(3) Uani 0.412(8) 1 d D U P A -1
C8 C -0.1669(11) 0.1418(8) 0.8396(8) 0.133(4) Uani 0.412(8) 1 d D U P A -1
H8A H -0.1202 0.1973 0.8583 0.199 Uiso 0.412(8) 1 calc R U P A -1
H8B H -0.2020 0.1151 0.8961 0.199 Uiso 0.412(8) 1 calc R U P A -1
H8C H -0.2179 0.1685 0.7947 0.199 Uiso 0.412(8) 1 calc R U P A -1
C9 C -0.0284(11) 0.0060(11) 0.8664(11) 0.101(4) Uani 0.412(8) 1 d D U P A -1
H9A H 0.0052 -0.0543 0.8387 0.152 Uiso 0.412(8) 1 calc R U P A -1
H9B H -0.0666 -0.0145 0.9233 0.152 Uiso 0.412(8) 1 calc R U P A -1
H9C H 0.0237 0.0570 0.8838 0.152 Uiso 0.412(8) 1 calc R U P A -1
C10 C -0.1798(6) -0.0326(8) 0.7594(6) 0.106(3) Uani 0.412(8) 1 d D U P A -1
H10A H -0.2226 -0.0074 0.7072 0.159 Uiso 0.412(8) 1 calc R U P A -1
H10B H -0.2236 -0.0525 0.8129 0.159 Uiso 0.412(8) 1 calc R U P A -1
H10C H -0.1401 -0.0922 0.7380 0.159 Uiso 0.412(8) 1 calc R U P A -1
C7' C -0.0950(7) 0.0799(8) 0.8065(6) 0.092(3) Uani 0.588(8) 1 d D U P A -2
C8' C -0.0810(8) 0.1677(5) 0.8807(5) 0.130(3) Uani 0.588(8) 1 d D U P A -2
H8'1 H -0.0083 0.1732 0.8980 0.196 Uiso 0.588(8) 1 calc R U P A -2
H8'2 H -0.1217 0.1522 0.9375 0.196 Uiso 0.588(8) 1 calc R U P A -2
H8'3 H -0.1043 0.2328 0.8532 0.196 Uiso 0.588(8) 1 calc R U P A -2
C9' C -0.0546(10) -0.0220(8) 0.8533(11) 0.147(5) Uani 0.588(8) 1 d D U P A -2
H9'1 H 0.0192 -0.0158 0.8658 0.221 Uiso 0.588(8) 1 calc R U P A -2
H9'2 H -0.0668 -0.0798 0.8102 0.221 Uiso 0.588(8) 1 calc R U P A -2
H9'3 H -0.0910 -0.0339 0.9133 0.221 Uiso 0.588(8) 1 calc R U P A -2
C10' C -0.2106(5) 0.0657(7) 0.7808(5) 0.133(3) Uani 0.588(8) 1 d D U P A -2
H10D H -0.2488 0.0452 0.8377 0.199 Uiso 0.588(8) 1 calc R U P A -2
H10E H -0.2174 0.0124 0.7321 0.199 Uiso 0.588(8) 1 calc R U P A -2
H10F H -0.2383 0.1306 0.7565 0.199 Uiso 0.588(8) 1 calc R U P A -2
C11 C -0.01860(15) 0.33550(15) 0.53900(17) 0.0586(6) Uani 1 1 d . . . . .
H11B H -0.0100 0.3329 0.4691 0.070 Uiso 1 1 calc R U . . .
H11A H -0.0897 0.3582 0.5525 0.070 Uiso 1 1 calc R U . . .
C12 C 0.2500 0.2500 0.7280(4) 0.0988(17) Uani 1 4 d DS TU P B .
H12A H 0.2538 0.1791 0.7048 0.148 Uiso 0.25 1 calc R U P . .
H12B H 0.1867 0.2822 0.7048 0.148 Uiso 0.25 1 calc R U P . .
H12C H 0.3095 0.2887 0.7048 0.148 Uiso 0.25 1 calc R U P . .
C13 C 0.2500 0.2500 0.8342(4) 0.0739(12) Uani 1 4 d DS TU P . .
C14 C 0.2452(7) 0.3410(5) 0.8836(5) 0.123(2) Uani 0.5 1 d D U P B -3
H14 H 0.2420 0.4038 0.8494 0.148 Uiso 0.5 1 calc R U P B -3
C15 C 0.2448(11) 0.3434(8) 0.9828(6) 0.172(3) Uani 0.5 1 d D U P B -3
H15 H 0.2412 0.4068 1.0159 0.207 Uiso 0.5 1 calc R U P B -3
C16 C 0.2500 0.2500 1.0324(7) 0.163(4) Uani 1 4 d DS TU P . .
H16 H 0.2500 0.2500 1.1002(17) 0.195 Uiso 1 4 d DS U P . .
O1 O 0.11722(11) 0.18352(11) 0.45412(10) 0.0654(5) Uani 1 1 d . . . . .
H1 H 0.1551 0.1353 0.4363 0.098 Uiso 1 1 calc R U . . .
H3 H -0.1044(19) 0.2468(19) 0.6930(16) 0.073(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.383(2) . ?
C1 C2 1.386(3) . ?
C1 C6 1.393(3) . ?
C2 C3 1.377(3) . ?
C2 C11 1.523(3) . ?
C3 C4 1.386(3) . ?
C3 H3 0.99(2) . ?
C4 C5 1.387(3) . ?
C4 C7 1.541(11) . ?
C4 C7' 1.553(9) . ?
C5 C6 1.374(3) . ?
C5 H5 0.9300 . ?
C6 C11 1.516(3) 3 ?
C7 C8 1.523(11) . ?
C7 C10 1.529(12) . ?
C7 C9 1.544(11) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C7' C10' 1.526(10) . ?
C7' C8' 1.527(10) . ?
C7' C9' 1.540(10) . ?
C8' H8'1 0.9600 . ?
C8' H8'2 0.9600 . ?
C8' H8'3 0.9600 . ?
C9' H9'1 0.9600 . ?
C9' H9'2 0.9600 . ?
C9' H9'3 0.9600 . ?
C10' H10D 0.9600 . ?
C10' H10E 0.9600 . ?
C10' H10F 0.9600 . ?
C11 C6 1.516(3) 4 ?
C11 H11B 0.9700 . ?
C11 H11A 0.9700 . ?
C12 C13 1.465(7) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.347(6) . ?
C14 C15 1.368(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.375(9) . ?
C15 H15 0.9300 . ?
C16 H16 0.93(2) . ?
O1 H1 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 118.59(17) . . ?
O1 C1 C6 120.16(17) . . ?
C2 C1 C6 121.2(2) . . ?
C3 C2 C1 118.37(18) . . ?
C3 C2 C11 119.89(18) . . ?
C1 C2 C11 121.69(19) . . ?
C2 C3 C4 122.7(2) . . ?
C2 C3 H3 118.2(13) . . ?
C4 C3 H3 119.1(13) . . ?
C3 C4 C5 116.7(2) . . ?
C3 C4 C7 126.3(5) . . ?
C5 C4 C7 116.3(5) . . ?
C3 C4 C7' 117.9(4) . . ?
C5 C4 C7' 125.3(4) . . ?
C6 C5 C4 123.20(19) . . ?
C6 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?
C5 C6 C1 117.83(18) . . ?
C5 C6 C11 120.11(18) . 3 ?
C1 C6 C11 122.0(2) . 3 ?
C8 C7 C10 109.3(9) . . ?
C8 C7 C4 109.0(8) . . ?
C10 C7 C4 113.7(8) . . ?
C8 C7 C9 109.4(9) . . ?
C10 C7 C9 107.6(8) . . ?
C4 C7 C9 107.8(10) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C10' C7' C8' 110.8(7) . . ?
C10' C7' C9' 108.6(8) . . ?
C8' C7' C9' 107.3(7) . . ?
C10' C7' C4 105.3(6) . . ?
C8' C7' C4 114.0(6) . . ?
C9' C7' C4 110.7(8) . . ?
C7' C8' H8'1 109.5 . . ?
C7' C8' H8'2 109.5 . . ?
H8'1 C8' H8'2 109.5 . . ?
C7' C8' H8'3 109.5 . . ?
H8'1 C8' H8'3 109.5 . . ?
H8'2 C8' H8'3 109.5 . . ?
C7' C9' H9'1 109.5 . . ?
C7' C9' H9'2 109.5 . . ?
H9'1 C9' H9'2 109.5 . . ?
C7' C9' H9'3 109.5 . . ?
H9'1 C9' H9'3 109.5 . . ?
H9'2 C9' H9'3 109.5 . . ?
C7' C10' H10D 109.5 . . ?
C7' C10' H10E 109.5 . . ?
H10D C10' H10E 109.5 . . ?
C7' C10' H10F 109.5 . . ?
H10D C10' H10F 109.5 . . ?
H10E C10' H10F 109.5 . . ?
C6 C11 C2 112.32(16) 4 . ?
C6 C11 H11B 109.1 4 . ?
C2 C11 H11B 109.1 . . ?
C6 C11 H11A 109.1 4 . ?
C2 C11 H11A 109.1 . . ?
H11B C11 H11A 107.9 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C13 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C12 120.3(4) . . ?
C13 C14 C15 121.6(7) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C14 C15 C16 118.5(10) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C15 C16 H16 119.8(5) . . ?
C1 O1 H1 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 178.84(16) . . . . ?
C6 C1 C2 C3 -0.8(3) . . . . ?
O1 C1 C2 C11 -3.9(3) . . . . ?
C6 C1 C2 C11 176.41(17) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C11 C2 C3 C4 -176.94(19) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C2 C3 C4 C7 -169.7(6) . . . . ?
C2 C3 C4 C7' 175.5(4) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C7 C4 C5 C6 171.1(5) . . . . ?
C7' C4 C5 C6 -174.8(5) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
C4 C5 C6 C11 177.21(19) . . . 3 ?
O1 C1 C6 C5 -178.54(17) . . . . ?
C2 C1 C6 C5 1.1(3) . . . . ?
O1 C1 C6 C11 3.3(3) . . . 3 ?
C2 C1 C6 C11 -177.02(17) . . . 3 ?
C3 C4 C7 C8 -17.3(11) . . . . ?
C5 C4 C7 C8 173.2(7) . . . . ?
C3 C4 C7 C10 104.9(8) . . . . ?
C5 C4 C7 C10 -64.6(10) . . . . ?
C3 C4 C7 C9 -135.9(7) . . . . ?
C5 C4 C7 C9 54.5(9) . . . . ?
C3 C4 C7' C10' 72.8(7) . . . . ?
C5 C4 C7' C10' -112.0(6) . . . . ?
C3 C4 C7' C8' -48.9(8) . . . . ?
C5 C4 C7' C8' 126.4(7) . . . . ?
C3 C4 C7' C9' -170.0(7) . . . . ?
C5 C4 C7' C9' 5.3(10) . . . . ?
C3 C2 C11 C6 88.5(2) . . . 4 ?
C1 C2 C11 C6 -88.7(2) . . . 4 ?
C12 C13 C14 C15 179.9(9) . . . . ?
C13 C14 C15 C16 0.3(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O1 0.82 2.09 2.678(2) 128.9 3
O1 H1 O1 0.82 2.09 2.678(2) 128.9 3

_refine_diff_density_max         0.188
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.033


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene'
