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_7158405
_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         'C29 H25 N9 O2, C H3 O'
_chemical_formula_sum            'C30 H28 N9 O3'
_chemical_formula_weight         562.61
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_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                 90.640(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.8236(2)
_cell_length_b                   23.2321(13)
_cell_length_c                   25.2997(15)
_cell_measurement_reflns_used    5075
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.543
_cell_measurement_theta_min      3.494
_cell_volume                     2835.0(3)
_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 0.998
_diffrn_measured_fraction_theta_max 0.994
_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  0.0836
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            29255
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.603
_diffrn_reflns_theta_min         3.494
_exptl_absorpt_coefficient_mu    0.731
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5659
_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
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       plate
_exptl_crystal_F_000             1180
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.785
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         5190
_refine_ls_number_restraints     84
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0907
_refine_ls_R_factor_gt           0.0762
_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^)+(0.1146P)^2^+1.9839P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2103
_refine_ls_wR_factor_ref         0.2220
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4135
_reflns_number_total             5190
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02032c2.cif
_cod_data_source_block           10
_cod_depositor_comments
'Adding full bibliography for 7158403--7158405.cif.'
_cod_database_code               7158405
_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,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C45 \\sim O46 \\sim C47 \\sim O48 \\sim C49 \\sim O50 \\sim C51 \\sim O52:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
3. Others
 Fixed Sof: H21(0.4) H21A(0.6) C22(0.4) H22A(0.4) H22B(0.4) C23(0.6) H23A(0.6)
 H23B(0.6) C24(0.4) H24(0.4) C25(0.4) H25(0.4) C26(0.4) H26A(0.4) H26B(0.4)
 C27(0.6) H27(0.6) C28(0.6) H28(0.6) C29(0.6) H29A(0.6) H29B(0.6) H30(0.4)
 H30A(0.6) C45(0.3) H45A(0.3) H45B(0.3) H45C(0.3) O46(0.3) C47(0.2) H47A(0.2)
 H47B(0.2) H47C(0.2) O48(0.2) C49(0.3) H49A(0.3) H49B(0.3) H49C(0.3) O50(0.3)
 C51(0.2) H51A(0.2) H51B(0.2) H51C(0.2) O52(0.2)
4.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C22(H22A,H22B), C23(H23A,H23B), C26(H26A,H26B), C29(H29A,
 H29B), C39(H39A,H39B)
4.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), N21(H21A), C24(H24), C25(H25), C27(H27), C28(H28), N30(H30),
 N30(H30A), C34(H34), C36(H36), C37(H37), C38(H38), C44(H44)
4.c Idealised Me refined as rotating group:
 C45(H45A,H45B,H45C), C47(H47A,H47B,H47C), C49(H49A,H49B,H49C), C51(H51A,H51B,
 H51C)
;
_shelx_res_checksum              58218
_olex2_submission_special_instructions 'No special instructions were received'