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_1502129
_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         'C46 H34 Cl4 N6 Zn2, 5(C3 H7 N O)'
_chemical_formula_sum            'C61 H69 Cl4 N11 O5 Zn2'
_chemical_formula_weight         1308.81
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2010-03-07T18:42:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                72.059(5)
_cell_angle_beta                 73.500(5)
_cell_angle_gamma                64.793(5)
_cell_formula_units_Z            2
_cell_length_a                   13.4654(14)
_cell_length_b                   14.1770(15)
_cell_length_c                   18.8934(19)
_cell_measurement_reflns_used    10656
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      1.00
_cell_volume                     3055.3(6)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0538
_diffrn_reflns_av_unetI/netI     0.0962
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20073
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         1.63
_exptl_absorpt_coefficient_mu    1.018
_exptl_absorpt_correction_T_max  0.9509
_exptl_absorpt_correction_T_min  0.7777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blade
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_platon_squeeze_details
;
The structure of the metal-organic compound was successfully solved in the 
triclinic space group P-1. Subsequent Fourier recycling allowed the 
identification of electron-density peaks that were attributed to DMF molecules
that appeared to be disordered. Despite the extensive use of restraints, no 
satisfactory models of the DMF molecules could be achieved. Additional 
electron-density peaks were found in the Fourier map, but could not be 
assigned to a certain solvent type. 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 a solvent-accessible void that accounts for 
approximately 39% of the unit-cell volume (i.e. 1185 A3) and 401 electrons 
per unit cell. Both the volume of the solvent-accessible void and the amount 
of the removed electrons correspond to 10 molecules of DMF per unit cell. 
  
The use of the SQUEEZE routine resulted in a appearance of a series of alerts 
in checkCIF report:
    - differences in the calculated and reported molecular weight (level A)
    - presence of a very large solvent accessible void (level A)
    - differences in the calculated and reported F000 value (level C)
    - differences in the calculated and reported formulas (level C) 
;
_refine_diff_density_max         1.148
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     518
_refine_ls_number_reflns         10718
_refine_ls_number_restraints     225
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.1129
_refine_ls_R_factor_gt           0.0716
_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^)+(0.1293P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1905
_refine_ls_wR_factor_ref         0.2067
_reflns_number_gt                6089
_reflns_number_total             10718
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol200532t_si_011.cif
_cod_data_source_block           6
_cod_original_cell_volume        3055.3(5)
_cod_database_code               1502129