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_7129660
_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 H84 N4 O4, 2(C H4 O)'
_chemical_formula_sum            'C70 H92 N4 O6'
_chemical_formula_weight         1085.47
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2022-01-23
_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                 90.126(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.9126(11)
_cell_length_b                   24.2434(15)
_cell_length_c                   15.1940(11)
_cell_measurement_reflns_used    1538
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.647
_cell_measurement_theta_min      1.584
_cell_volume                     6229.8(7)
_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 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.7288
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            85343
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.930
_diffrn_reflns_theta_max         26.194
_diffrn_reflns_theta_min         1.846
_diffrn_source                   'Advanced Light Source station 12.2.1'
_diffrn_source_current           10.0
_diffrn_source_power             0.2
_diffrn_source_voltage           20.0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0966 before and 0.0764 after correction.
The Ratio of minimum to maximum transmission is 0.7589.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_description       Plate
_exptl_crystal_F_000             2352
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     782
_refine_ls_number_reflns         11523
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0533
_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^)+(0.0881P)^2^+2.3545P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1495
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10200
_reflns_number_total             11523
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06889j2.cif
_cod_data_source_block           5A
_cod_database_code               7129660
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.992
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.52366
 0.47634
2. Rigid body (RIGU) restrains
 C33, C34, C35, C36, C34', C35', C36'
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Others
 Sof(C34')=Sof(H34D)=Sof(H34E)=Sof(H34F)=Sof(C35')=Sof(H35D)=Sof(H35E)=
 Sof(H35F)=Sof(C36')=Sof(H36D)=Sof(H36E)=Sof(H36F)=1-FVAR(1)
 Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(H34C)=Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(H35C)=
 Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(H36C)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C7(H7), C14(H14), C21(H21), C28(H28)
4.b Me refined with riding coordinates:
 C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C34(H34A,H34B,
 H34C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C34'(H34D,H34E,H34F),
 C35'(H35D,H35E,H35F), C36'(H36D,H36E,H36F), 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)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3), N4(H4), C2(H2A), C4(H4A), C9(H9), C11(H11), C16(H16),
 C18(H18), C23(H23), C25(H25), C50(H50), C51(H51), C55(H55), C56(H56), C60(H60),
  C61(H61), C65(H65), C66(H66)
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_shelx_res_checksum              93888
_shelx_hkl_checksum              12243
_olex2_submission_special_instructions 'No special instructions were received'