Synthesis of pyridine-fused perylene imides with an amidine moiety for hydrogen bonding.
Ito, Satoru; Hiroto, Satoru; Shinokubo, Hiroshi; Organic letters 15 (2013) 3110–3113; doi:10.1021/ol401316q

data_1556188
_publ_section_title
;
 Synthesis of pyridine-fused perylene imides with an amidine moiety for
 hydrogen bonding.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3110
_journal_page_last               3113
_journal_paper_doi               10.1021/ol401316q
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C40.6 H39.25 Cl0.35 F5 N1.5 O4'
_chemical_formula_weight         719.59
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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_method           SHELXL-97
_cell_angle_alpha                70.46(2)
_cell_angle_beta                 85.66(3)
_cell_angle_gamma                76.63(3)
_cell_formula_units_Z            4
_cell_length_a                   6.872(3)
_cell_length_b                   22.864(7)
_cell_length_c                   25.039(9)
_cell_measurement_reflns_used    4550
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      27.39
_cell_measurement_theta_min      3.02
_cell_volume                     3607(2)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        CrystalClear
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.2092
_diffrn_reflns_av_sigmaI/netI    0.3183
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            24292
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.9987
_exptl_absorpt_correction_T_min  0.9726
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1505
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.664
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     940
_refine_ls_number_reflns         12439
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.3475
_refine_ls_R_factor_gt           0.1691
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3912
_refine_ls_wR_factor_ref         0.4973
_reflns_number_gt                3442
_reflns_number_total             12439
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401316q_si_002.cif
_cod_data_source_block           shelxl
_cod_original_formula_sum        'C40.60 H39.25 Cl0.35 F5 N1.50 O4'
_cod_database_code               1556188