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_7129654
_publ_section_title
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 Facile Synthetic Routes to Bridge-Functionalised Calix[4]arenes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06889J
_journal_year                    2022
_chemical_formula_moiety         'C68 H88 O12'
_chemical_formula_sum            'C68 H88 O12'
_chemical_formula_weight         1097.38
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-01-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-01-22 deposited with the CCDC.	2022-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.046(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0103(6)
_cell_length_b                   19.7417(9)
_cell_length_c                   24.1171(10)
_cell_measurement_reflns_used    9744
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      38.04
_cell_measurement_theta_min      2.43
_cell_volume                     6193.3(5)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'Apex II (Bruker)'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.7749
_diffrn_reflns_av_R_equivalents  0.0780
_diffrn_reflns_av_unetI/netI     0.0718
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            80335
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        27.706
_diffrn_reflns_theta_max         33.632
_diffrn_reflns_theta_min         1.453
_diffrn_source                   'Advanced Light Source station 11.3.1'
_diffrn_source_current           10.0
_diffrn_source_power             0.2
_diffrn_source_voltage           20.0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_correction_T_min  0.6697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1264 before and 0.0996 after correction.
The Ratio of minimum to maximum transmission is 0.8970.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_description       Plate
_exptl_crystal_F_000             2368
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     777
_refine_ls_number_reflns         18907
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0629
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1040P)^2^+1.7309P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1747
_refine_ls_wR_factor_ref         0.1856
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15573
_reflns_number_total             18907
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06889j2.cif
_cod_data_source_block           3
_cod_database_code               7129654
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.986
_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
2. Restrained distances
 C54-O7 \\sim C54-O7'
 with sigma of 0.01
3. Others
 Fixed Sof: O7(0.6) O8(0.6) C56(0.6) H56A(0.6) H56B(0.6) C55(0.6) H55A(0.6)
 H55B(0.6) C70(0.4) H70A(0.4) H70B(0.4) O13(0.4) C69(0.4) H69A(0.4) H69B(0.4)
 O7'(0.4)
4.a Ternary CH refined with riding coordinates:
 C7(H7), C14(H14), C21(H21), C28(H28)
4.b Secondary CH2 refined with riding coordinates:
 C56(H56A,H56B), C50(H50A,H50B), C51(H51A,H51B), C55(H55A,H55B), C60(H60A,
 H60B), C61(H61A,H61B), C65(H65A,H65B), C66(H66A,H66B), C70(H70A,H70B),
 C69(H69A,H69B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C9(H9), C11(H11), C16(H16), C18(H18), C23(H23), C25(H25)
4.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C34(H34A,H34B,
 H34C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C38(H38A,H38B,H38C), C39(H39A,
 H39B,H39C), C40(H40A,H40B,H40C), C42(H42A,H42B,H42C), C43(H43A,H43B,H43C),
 C44(H44A,H44B,H44C), C45(H45A,H45B,H45C), C46(H46A,H46B,H46C), C47(H47A,H47B,
 H47C), C48(H48A,H48B,H48C), C53(H53A,H53B,H53C), C58(H58A,H58B,H58C), C63(H63A,
 H63B,H63C), C68(H68A,H68B,H68C)
;
_shelx_res_checksum              63253
_shelx_hkl_checksum              12562
_olex2_submission_special_instructions 'No special instructions were received'