Extreme Stabilization and Redox Switching of Organic Anions and Radical Anions by Large-Cavity, CH Hydrogen-Bonding Cyanostar Macrocycles.
Benson, Christopher R.; Fatila, Elisabeth M.; Lee, Semin; Marzo, Matthew G.; Pink, Maren; Mills, Michelle B.; Preuss, Kathryn E.; Flood, Amar H.; Journal of the American Chemical Society 138 (2016) 15057–15065; doi:10.1021/jacs.6b09459

data_4131118
_publ_section_title
;
 Extreme Stabilization and Redox Switching of Organic Anions and Radical
 Anions by Large-Cavity, CH Hydrogen-Bonding Cyanostar Macrocycles.
;
_journal_issue                   45
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15057
_journal_page_last               15065
_journal_paper_doi               10.1021/jacs.6b09459
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         '2 (C65 H65 N5), C16 H14 N4, 2(C H2 Cl2)'
_chemical_formula_sum            'C148 H148 Cl4 N14'
_chemical_formula_weight         2264.60
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                79.5333(16)
_cell_angle_beta                 74.5056(16)
_cell_angle_gamma                82.7214(17)
_cell_formula_units_Z            1
_cell_length_a                   13.9614(4)
_cell_length_b                   15.5727(5)
_cell_length_c                   18.4333(6)
_cell_measurement_reflns_used    9722
_cell_measurement_temperature    230(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      2.32
_cell_volume                     3784.8(2)
_computing_cell_refinement       'APEX II v2014.11-0 (Bruker, 2014)'
_computing_data_collection       'APEX II v2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'APEX II v2014.11-0 (Bruker, 2014)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2014)'
_computing_publication_material  'SHELXTL (Bruker, 2014)'
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_computing_structure_solution    'SHELX (Bruker, 2014)'
_diffrn_ambient_temperature      230(2)
_diffrn_detector                 'CCD area detector'
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_diffrn_detector_type            'Bruker APEXII'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
'0.50 degree frames measured for 90 seconds each'
_diffrn_measurement_device       'APEX Kappa Duo'
_diffrn_measurement_device_type  Kappa
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            55177
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.091
_diffrn_reflns_theta_max         25.091
_diffrn_reflns_theta_min         1.160
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6476
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, G. Sheldrick; 2016'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    0.994
_exptl_crystal_description       plate
_exptl_crystal_F_000             1202
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.120
_refine_diff_density_max         1.170
_refine_diff_density_min         -0.655
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     972
_refine_ls_number_reflns         13409
_refine_ls_number_restraints     2868
_refine_ls_restrained_S_all      1.982
_refine_ls_R_factor_all          0.1776
_refine_ls_R_factor_gt           0.1507
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4617
_refine_ls_wR_factor_ref         0.4845
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9328
_reflns_number_total             13409
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b09459_si_002.cif
_cod_data_source_block           16016_sq
_cod_original_cell_volume        3784.9(2)
_cod_database_code               4131118
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.969
_shelx_estimated_absorpt_t_max   0.985
_shelx_res_checksum              12300
_shelx_hkl_checksum              53304
_shelx_fab_checksum              82478