High yielding synthesis of 2,2′-bipyridine macrocycles, versatile intermediates in the synthesis of rotaxanes
Lewis, J. E. M.; Bordoli, R. J.; Denis, M.; Fletcher, C. J.; Galli, M.; Neal, E. A.; Rochette, E. M.; Goldup, S. M.; Chem. Sci. 7 (2016) 3154–; doi:10.1039/C6SC00011H

data_1542335
_publ_section_title
;
 High yielding synthesis of 2,2&#x2032;-bipyridine macrocycles, versatile
 intermediates in the synthesis of rotaxanes
;
_journal_issue                   5
_journal_name_full               'Chem. Sci.'
_journal_page_first              3154
_journal_paper_doi               10.1039/C6SC00011H
_journal_volume                  7
_journal_year                    2016
_chemical_formula_sum            'C33 H34.5 Cl2.5 Cu F6 N3 O4 P'
_chemical_formula_weight         834.27
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-12-15 deposited with the CCDC.
2016-01-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.456(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.590(3)
_cell_length_b                   17.504(4)
_cell_length_c                   28.499(6)
_cell_measurement_reflns_used    14477
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      2.2
_cell_volume                     7133(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0795
_diffrn_reflns_av_unetI/netI     0.0665
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            70413
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.566
_diffrn_reflns_theta_min         2.232
_exptl_absorpt_coefficient_mu    0.918
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_description       block
_exptl_crystal_F_000             3408
_exptl_crystal_size_max          0.069
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.024
_refine_diff_density_max         2.927
_refine_diff_density_min         -1.731
_refine_diff_density_rms         0.154
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.267
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     957
_refine_ls_number_reflns         16433
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.268
_refine_ls_R_factor_all          0.1628
_refine_ls_R_factor_gt           0.1095
_refine_ls_shift/su_max          0.047
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3244
_refine_ls_wR_factor_ref         0.3630
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9992
_reflns_number_total             16433
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc00011h2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
Adding full bibliography for 1542335--1542337.cif.

2019-07-14
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C66 H69 Cl5 Cu2 F12 N6 O8 P2'
_cod_original_formula_weight         1668.54
_cod_original_formula_units_Z            4
_cod_database_code               1542335
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              83898
_shelx_hkl_checksum              13555