Bis-thioether-Substituted Perylene Diimides: Structural, Electrochemical, and Spectroelectrochemical Properties
Anna G. Slater; E. Stephen Davies; Stephen P. Argent; William Lewis; Alexander J. Blake; Jonathan McMaster; Neil R. Champness; Journal of Organic Chemistry 78 (2013) 2853–2862; doi:10.1021/jo400026r

data_4028084
_publ_section_title
;
 Bis-thioether-Substituted Perylene Diimides: Structural, Electrochemical,
 and Spectroelectrochemical Properties
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2853
_journal_page_last               2862
_journal_paper_doi               10.1021/jo400026r
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C74 H82 N2 O8 S2'
_chemical_formula_sum            'C74 H82 N2 O8 S2'
_chemical_formula_weight         1191.54
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'enCIFer editing of SHELXL97 CIF output'
_cell_angle_alpha                90.00
_cell_angle_beta                 113.399(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.6220(10)
_cell_length_b                   20.8987(7)
_cell_length_c                   16.5571(10)
_cell_measurement_reflns_used    16907
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      74.35
_cell_measurement_theta_min      3.24
_cell_volume                     6231.3(6)
_computing_cell_refinement
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) 
(compiled Jan  5 2010,16:28:46) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
;
_computing_data_collection
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) 
(compiled Jan  5 2010,16:28:46) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
;
_computing_data_reduction
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) 
(compiled Jan  5 2010,16:28:46) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
;
_computing_molecular_graphics    ' ?'
_computing_publication_material
'enCIFer (Allen et al., 2004); PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    ' ?'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 10.3613
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) x-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.089
_diffrn_reflns_av_sigmaI/netI    0.062
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            37706
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         75.00
_diffrn_reflns_theta_min         3.24
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.247
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.806
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) 
(compiled Jan  5 2010,16:28:46) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       plate
_exptl_crystal_F_000             2544
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.53
_refine_diff_density_min         -0.48
_refine_diff_density_rms         0.11
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.11
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     775
_refine_ls_number_reflns         12417
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.11
_refine_ls_R_factor_all          0.154
_refine_ls_R_factor_gt           0.112
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.053P)^2^+44.69P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.255
_refine_ls_wR_factor_ref         0.281
_reflns_number_gt                8603
_reflns_number_total             12417
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400026r_si_002_2.cif
_cod_data_source_block           1c
_cod_original_cell_volume        6231.3(5)
_cod_database_code               4028084
_nottingham_internal_coll_name   PERAPB
_nottingham_internal_coll_number 9125
_nottingham_internal_coll_client AGP/NRC
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_time '10 and 40s'
_nottingham_internal_coll_frame_width '1 degree'
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_user   WL
_nottingham_internal_coll_date   22/2/2010
_nottingham_internal_process_user WL
_nottingham_internal_process_date 22/02/2010
_nottingham_internal_solution_user SPA/AGP
_nottingham_internal_solution_date 22/02/10
_nottingham_internal_refinement_user SPA/AGP
_nottingham_internal_refinement_date 22/02/10
_nottingham_internal_validation_user AJB
_nottingham_internal_validation_date 1/5/2010