Singlet Fission via an Excimer-Like Intermediate in 3,6-Bis(thiophen-2-yl)diketopyrrolopyrrole Derivatives.
Mauck, Catherine M.; Hartnett, Patrick E.; Margulies, Eric A.; Ma, Lin; Miller, Claire E.; Schatz, George C.; Marks, Tobin J.; Wasielewski, Michael R.; Journal of the American Chemical Society 138 (2016) 11749–11761; doi:10.1021/jacs.6b05627

data_4130654
_publ_section_title
;
 Singlet Fission via an Excimer-Like Intermediate in
 3,6-Bis(thiophen-2-yl)diketopyrrolopyrrole Derivatives.
;
_journal_issue                   36
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11749
_journal_page_last               11761
_journal_paper_doi               10.1021/jacs.6b05627
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C16 H12 N2 O2 S2'
_chemical_formula_sum            'C16 H12 N2 O2 S2'
_chemical_formula_weight         328.40
_chemical_name_systematic        Me2TDPP
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-01-20
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 154.939(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.2356(9)
_cell_length_b                   12.9918(10)
_cell_length_c                   11.3681(10)
_cell_measurement_reflns_used    3395
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.91
_cell_measurement_theta_min      5.26
_cell_volume                     702.90(14)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.1-4 (Bruker, 2007)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.934
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Quazar optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.934
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3754
_diffrn_reflns_point_group_measured_fraction_full 0.934
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         64.907
_diffrn_reflns_theta_min         5.261
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    3.511
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.5503
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0773 before and 0.0339 after correction.
The Ratio of minimum to maximum transmission is 0.7312.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_description       needle
_exptl_crystal_F_000             340
_exptl_crystal_size_max          1.674
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1184
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0320
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0578P)^2^+0.3396P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.0945
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1162
_reflns_number_total             1184
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b05627_si_002.cif
_cod_data_source_block           me2tdpp_x
_cod_original_cell_volume        702.90(11)
_cod_database_code               4130654
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.814
_shelx_estimated_absorpt_t_min   0.067
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10)
2.b Idealised Me refined as rotating group:
 C5(H5a,H5b,H5c)
;
_shelx_res_checksum              65005
_shelx_hkl_checksum              57762
_olex2_submission_special_instructions 'No special instructions were received'