A non-cross-coupling approach to arene-bridged macrocycles: synthesis, structure, and direct, regioselective functionalization of a cycloparaphenylene fragment.
Mitra, Nirmal K.; Meudom, Rolande; Gorden, John D.; Merner, Bradley L.; Organic letters 17 (2015) 2700–2703; doi:10.1021/acs.orglett.5b01102

data_1519695
_publ_section_title
;
 A non-cross-coupling approach to arene-bridged macrocycles: synthesis,
 structure, and direct, regioselective functionalization of a
 cycloparaphenylene fragment.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2700
_journal_page_last               2703
_journal_paper_doi               10.1021/acs.orglett.5b01102
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C23 H22 O2'
_chemical_formula_sum            'C23 H22 O2'
_chemical_formula_weight         330.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.099(3)
_cell_length_b                   13.445(4)
_cell_length_c                   16.407(5)
_cell_measurement_reflns_used    1294
_cell_measurement_temperature    180.(2)
_cell_measurement_theta_max      21.4020
_cell_measurement_theta_min      2.4828
_cell_volume                     1786.6(10)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      180.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0708
_diffrn_reflns_av_unetI/netI     0.0677
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10323
_diffrn_reflns_theta_full        25.73
_diffrn_reflns_theta_max         25.73
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  .996
_exptl_absorpt_correction_T_min  .993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Fragment
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.127
_refine_ls_abs_structure_details
;
Flack x determined using 663 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.9(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2402
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0271P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0680
_refine_ls_wR_factor_ref         0.0721
_reflns_number_gt                1911
_reflns_number_total             2402
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01102_si_002.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 1519695.cif.'
_cod_original_cell_volume        1786.6(9)
_cod_database_code               1519695