Facile Synthetic Routes to Bridge-Functionalised Calix[4]arenes
Fong, Angela; Cambell, Cameron; Huynh, Silvia; McCormick McPherson, Laura J.; Teat, Simon; Bebbington, Magnus W. P.; Dalgarno, Scott; Chemical Communications  (2022) –; doi:10.1039/D1CC06889J

data_7129656
_publ_section_title
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 Facile Synthetic Routes to Bridge-Functionalised Calix[4]arenes
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_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06889J
_journal_year                    2022
_chemical_formula_moiety         'C64 H72 N8 O4'
_chemical_formula_sum            'C64 H72 N8 O4'
_chemical_formula_weight         1017.29
_space_group_crystal_system      tetragonal
_space_group_IT_number           82
_space_group_name_Hall           'I -4'
_space_group_name_H-M_alt        'I -4'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-12-07
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-01-23 deposited with the CCDC.	2022-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.0951(5)
_cell_length_b                   12.0951(5)
_cell_length_c                   22.4894(10)
_cell_measurement_reflns_used    983
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      12.44
_cell_measurement_theta_min      2.40
_cell_volume                     3290.0(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Apex II CCD diffractometer'
_diffrn_measurement_method       '\w rotation with narrow frames'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.7288
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            42098
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.930
_diffrn_reflns_theta_max         26.112
_diffrn_reflns_theta_min         1.960
_diffrn_source                   'Advanced Light Source station 12.2.1'
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0956 before and 0.0669 after correction.
The Ratio of minimum to maximum transmission is 0.8740.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.027
_exptl_crystal_description       plate
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1283 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3026
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0534
_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^)+(0.1224P)^2^+0.1217P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1490
_refine_ls_wR_factor_ref         0.1523
_reflns_Friedel_coverage         0.934
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                2812
_reflns_number_total             3026
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06889j2.cif
_cod_data_source_block           6
_cod_original_cell_volume        3290.0(3)
_cod_database_code               7129656
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.995
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C7(H7)
1.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C13(H13), C14(H14)
1.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C16(H16A,H16B,H16C)
1.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              55769
_shelx_hkl_checksum              47145
_olex2_submission_special_instructions 'No special instructions were received'