Phthalimide-based pi-conjugated small molecules with tailored electronic energy levels for use as acceptors in organic solar cells
Arthur D. Hendsbee; Seth M. McAfee; Jon-Paul Sun; Theresa M. McCormick; Ian G. Hill; Gregory C. Welch; Journal of Materials Chemistry C 3 (2015) 8904–8915; doi:10.1039/C5TC01877C

data_7234414
_publ_section_exptl_refinement
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The H atoms were placed in geometrically idealized positions with C-H 
distances of 0.95\%A (aromatic),1.0\%A (idealized CH), 0.99\%A 
(idealized CH~2~) and 0.98\%A
(idealized CH~3~) and were constrained to ride on the parent C atom 
with Uiso(H) = 1.2Ueq(C) for the aromatic, CH~2~ and C-H protons and Uiso(H) 
= 1.5Ueq(C) for the idealized CH~3~ protons. 

For the 2-ethylpropyl alkyl chain containing carbon atoms C25-C29 a disorder 
was modelled with a ratio of 1:1.The atomic displacement parameters for 
carbon atoms on the disordered fragment were restraied to be of similar 
size using the DELU and SIMU commands.  
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_publ_section_title
;
 Phthalimide-based pi-conjugated small molecules with tailored electronic
 energy levels for use as acceptors in organic solar cells
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_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              8904
_journal_page_last               8915
_journal_paper_doi               10.1039/C5TC01877C
_journal_volume                  3
_journal_year                    2015
_chemical_formula_sum            'C58 H56 N4 O8 S2'
_chemical_formula_weight         1001.19
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 99.160(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.612(3)
_cell_length_b                   11.4854(13)
_cell_length_c                   20.156(2)
_cell_measurement_reflns_used    5593
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      2.17
_cell_volume                     5167.9(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_av_sigmaI/netI    0.0534
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            26224
_diffrn_reflns_theta_full        25.84
_diffrn_reflns_theta_max         25.84
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker 2008)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2112
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2'
_exptl_crystal_size_max          .298
_exptl_crystal_size_mid          .241
_exptl_crystal_size_min          .232
_refine_diff_density_max         0.819
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     377
_refine_ls_number_reflns         4982
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0556
_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^)+(0.0796P)^2^+4.5009P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1623
_reflns_number_gt                3334
_reflns_number_total             4982
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2015-3-8904.cif
_cod_data_source_block           20150109_art2_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7234414