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_7129658
_publ_section_title
;
 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         'C88 H96 N8 O4'
_chemical_formula_sum            'C88 H96 N8 O4'
_chemical_formula_weight         1329.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-01-24
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-01-24 deposited with the CCDC.	2022-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.163(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.153(9)
_cell_length_b                   11.480(6)
_cell_length_c                   21.506(12)
_cell_measurement_reflns_used    836
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      11.82
_cell_measurement_theta_min      2.31
_cell_volume                     3767(4)
_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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.858
_diffrn_measured_fraction_theta_max 0.860
_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_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.858
_diffrn_reflns_Laue_measured_fraction_max 0.860
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5337
_diffrn_reflns_point_group_measured_fraction_full 0.858
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        23.938
_diffrn_reflns_theta_max         23.938
_diffrn_reflns_theta_min         1.369
_diffrn_source                   'Advanced Light Source station 12.2.1'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0686 before and 0.0527 after correction.
 The Ratio of minimum to maximum transmission not present.
 The \l/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.0818 before and 0.0498 after correction.
 The Ratio of minimum to maximum transmission is 0.87.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 40955 reflections, Rint = 0.1040
 (22565 with I > 3sig(I), Rint = 0.0639)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   0.745
_exptl_transmission_factor_min   0.649
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     510
_refine_ls_number_reflns         5337
_refine_ls_number_restraints     144
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0581
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0834P)^2^+3.3128P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1480
_refine_ls_wR_factor_ref         0.1598
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4486
_reflns_number_total             5337
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06889j2.cif
_cod_data_source_block           5D
_cod_database_code               7129658
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.976
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.50248
 0.49752
2. Rigid body (RIGU) restrains
 C15, C16, C18, C20, C17, C19, C21
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C22, C24, C26, C28, C23, C25, C27
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N3, C36, C37, C38, C39, C40
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N4, C46, C47, C48, C49, C50
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3. Others
 Fixed Sof: C16(0.333) H16A(0.333) H16B(0.333) H16C(0.333) C18(0.333)
 H18A(0.333) H18B(0.333) H18C(0.333) C20(0.333) H20A(0.333) H20B(0.333)
 H20C(0.333) C24(0.5) H24A(0.5) H24B(0.5) H24C(0.5) C26(0.5) H26A(0.5)
 H26B(0.5) H26C(0.5) C28(0.5) H28A(0.5) H28B(0.5) H28C(0.5) C17(0.667)
 H17A(0.667) H17B(0.667) H17C(0.667) C19(0.667) H19A(0.667) H19B(0.667)
 H19C(0.667) C21(0.667) H21A(0.667) H21B(0.667) H21C(0.667) C23(0.5) H23A(0.5)
 H23B(0.5) H23C(0.5) C25(0.5) H25A(0.5) H25B(0.5) H25C(0.5) C27(0.5) H27A(0.5)
 H27B(0.5) H27C(0.5)
4.a Ternary CH refined with riding coordinates:
 C7(H7), C14(H14)
4.b Me refined with riding coordinates:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C24(H24A,H24B,
 H24C), C26(H26A,H26B,H26C), C28(H28A,H28B,H28C), C17(H17A,H17B,H17C), C19(H19A,
 H19B,H19C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C),
 C27(H27A,H27B,H27C)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C9(H9), C11(H11), C32(H32), C33(H33), C37(H37), C38(H38),
 C39(H39), C40(H40), C42(H42), C43(H43), C47(H47), C48(H48), C49(H49), C50(H50)
4.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C35(H35A,H35B,H35C), C45(H45A,H45B,
 H45C)
;
_shelx_res_checksum              17114
_shelx_hkl_checksum              67798
_olex2_submission_special_instructions 'No special instructions were received'