Macrocyclic <i>vs.</i> [2]catenane btp structures: influence of (aryl) substitution on the self templation of btp ligands in macrocyclic synthesis.
McCarney, Eoin P.; McCarthy, William J.; Lovitt, June I.; Gunnlaugsson, Thorfinnur; Organic & biomolecular chemistry 19 (2021) 10189–10200; doi:10.1039/d1ob02032c

data_7158403
_publ_section_title
;
 Macrocyclic <i>vs.</i> [2]catenane btp structures: influence of (aryl)
 substitution on the self templation of btp ligands in macrocyclic
 synthesis.
;
_journal_issue                   46
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10189
_journal_page_last               10200
_journal_paper_doi               10.1039/d1ob02032c
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C31 H29 N9 O2, C H4 O'
_chemical_formula_sum            'C32 H33 N9 O3'
_chemical_formula_weight         591.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2021-10-14 deposited with the CCDC.	2021-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.802(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.5957(3)
_cell_length_b                   22.3241(11)
_cell_length_c                   14.0970(9)
_cell_measurement_reflns_used    2493
_cell_measurement_temperature    99.99
_cell_measurement_theta_max      51.589
_cell_measurement_theta_min      3.139
_cell_volume                     1444.55(15)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      99.99
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6746
_diffrn_reflns_point_group_measured_fraction_full 0.940
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        52.289
_diffrn_reflns_theta_max         52.289
_diffrn_reflns_theta_min         3.139
_diffrn_source_current           0.65
_diffrn_source_power             0.0290615
_diffrn_source_voltage           44.71
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.743
_exptl_absorpt_correction_T_max  0.7503
_exptl_absorpt_correction_T_min  0.6017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0863 before and 0.0531 after correction.
The Ratio of minimum to maximum transmission is 0.8019.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1160 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         3090
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0434
_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^)+(0.0758P)^2^+0.0453P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1150
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_full    0.892
_reflns_Friedel_fraction_max     0.892
_reflns_number_gt                2748
_reflns_number_total             3090
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02032c2.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 7158403--7158405.cif.'
_cod_database_code               7158403
_shelx_shelxl_version_number     2016/4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C22(H22A,H22B), C30(H30A,H30B), C40(H40A,H40B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C11(H11), C14(H14), C15(H15), C16(H16), C18(H18),
 N21(H21), C23(H23), C29(H29), C32(H32), C33(H33), C34(H34), C36(H36), N39(H39),
  C41(H41)
2.c Idealised Me refined as rotating group:
 C44(H44A,H44B,H44C)
2.d Idealised tetrahedral OH refined as rotating group:
 O43(H43)
;
_shelx_res_checksum              78401
_olex2_submission_special_instructions 'No special instructions were received'