Resorcinol-templated synthesis of a cofacial terpyridine in crystalline π-stacked columns.
Dutta, Saikat; Bučar, Dejan-Krešimir; MacGillivray, Leonard R.; Organic letters 13 (2011) 2260–2262; doi:10.1021/ol200532t

data_1502130
_publ_section_title
;
 Resorcinol-templated synthesis of a cofacial terpyridine in crystalline
 \p-stacked columns.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2260
_journal_page_last               2262
_journal_paper_doi               10.1021/ol200532t
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C92 H68 N12 O4 Cu4 , 8(N O3)'
_chemical_formula_sum            'C92 H68 Cu4 N20 O28'
_chemical_formula_weight         2155.86
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2010-03-10T23:25:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 100.895(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   30.119(4)
_cell_length_b                   20.405(3)
_cell_length_c                   16.2840(17)
_cell_measurement_reflns_used    22835
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      1.00
_cell_volume                     9827(2)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.03
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            30099
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         6.02
_exptl_absorpt_coefficient_mu    0.941
_exptl_absorpt_correction_T_max  0.8109
_exptl_absorpt_correction_T_min  0.7139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             4400
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_platon_squeeze_details
;
The structure of the investigated compound was successfully solved in the 
monoclinic space group C 2/c. Subsequent Fourier recycling allowed the 
identification of electron-density peaks that were asigned to disordered 
methanol and water molecules. Despite the extensive use of restraints, 
no satisfactory models of the disordered molecules could be achieved. 
The dataset was therefore treated with the SQUEEZE routine in Platon 
(P. van der Sluis, A. L. Spek, Acta Crystallogr. 1990, A46, 194.) to remove 
electron densities arising from the solvent molecules. Platon identified 
solvent-accessible voids that account for approximately 10% of the unit-cell 
volume (i.e. 998 A3) and 566 electrons per unit cell. The volume of the 
solvent-accessible voids was comparable to the volume of solvent molecules
identified in the Fourier map. At the same time. the number of electrons 
removed from the original hkl file strongly disagreed with the number of 
electrons belonging to solvent molecules identified in the Fourier map. 
The composition of the investigated single crystal could, therefore, not be 
determined. Calculated quantities such as formula, density, F(000) and absorption 
coefficient are, consequently, reported without the solvent contribution and 
are not describing the true nature of the investigated single crystal.
;
_refine_diff_density_max         1.117
_refine_diff_density_min         -0.968
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     636
_refine_ls_number_reflns         8521
_refine_ls_number_restraints     112
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.088
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1603P)^2^+30.7527P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2543
_refine_ls_wR_factor_ref         0.2662
_reflns_number_gt                6995
_reflns_number_total             8521
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol200532t_si_013.cif
_cod_data_source_block           7
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1502130