Synthesis of [8]Cycloparaphenylene-octacarboxylates via Rh-Catalyzed Stepwise Cross-Alkyne Cyclotrimerization
Hayase, Norihiko; Miyauchi, Yuta; Aida, Yukimasa; Sugiyama, Haruki; Uekusa, Hidehiro; Shibata, Yu; Tanaka, Ken; Organic Letters  (2017) –; doi:10.1021/acs.orglett.7b01231

data_1546039
_publ_section_title
;
 Synthesis of [8]Cycloparaphenylene-octacarboxylates via Rh-Catalyzed
 Stepwise Cross-Alkyne Cyclotrimerization
;
_journal_name_full               'Organic Letters'
_journal_paper_doi               10.1021/acs.orglett.7b01231
_journal_year                    2017
_chemical_formula_moiety         'C94.67 H110.34 O17.84'
_chemical_formula_sum            'C94.67 H110.34 O17.84'
_chemical_formula_weight         1533.60
_chemical_name_systematic        ring
_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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 94.4140(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.6554(5)
_cell_length_b                   26.5185(5)
_cell_length_c                   26.1889(5)
_cell_measurement_reflns_used    83296
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3.21
_cell_volume                     19149.4(6)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_computing_publication_material  'SHELXL-2014/07 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID-II IP Area Detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            180231
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         68.211
_diffrn_reflns_theta_min         3.206
_diffrn_source                   'rotating anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.585
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Absorption was corrected by ABSCOR'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.064
_exptl_crystal_description       plate
_exptl_crystal_F_000             6568
_exptl_crystal_size_max          0.368
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.108
_refine_diff_density_max         1.020
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2107
_refine_ls_number_reflns         34373
_refine_ls_number_restraints     155
_refine_ls_restrained_S_all      1.367
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0676
_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^)+(0.1377P)^2^+3.9145P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2138
_refine_ls_wR_factor_ref         0.2326
_reflns_Friedel_coverage         0.000
_reflns_number_gt                25108
_reflns_number_total             34373
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01231_si_002.cif
_cod_data_source_block           shelxt_sq
_cod_database_code               1546039
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.813
_shelx_estimated_absorpt_t_max   0.940
_shelx_res_checksum              71148
_shelx_hkl_checksum              97712
_shelx_fab_checksum              15969