Synthesis and characterization of fluorinated azadipyrromethene complexes as acceptors for organic photovoltaics.
Etheridge, Forrest S.; Fernando, Roshan J.; Pejić, Sandra; Zeller, Matthias; Sauvé, Geneviève; Beilstein journal of organic chemistry 12 (2016) 1925–1938; doi:10.3762/bjoc.12.182

data_4032050
_publ_section_title
;
 Synthesis and characterization of fluorinated azadipyrromethene complexes
 as acceptors for organic photovoltaics.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              1925
_journal_page_last               1938
_journal_paper_doi               10.3762/bjoc.12.182
_journal_volume                  12
_journal_year                    2016
_chemical_formula_moiety         'C96 H56 F4 N6 Zn, C H2 Cl2'
_chemical_formula_sum            'C97 H58 Cl2 F4 N6 Zn'
_chemical_formula_weight         1519.76
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_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
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_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.237
_cell_measurement_theta_min      4.056
_cell_volume                     7298.8(13)
_computing_cell_refinement       'HKL3000 (Otwinowski & Minor, 1997)'
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_computing_data_reduction        'HKL3000 (Otwinowski & Minor, 1997)'
_computing_structure_refinement
;  
SHELXL-2014/7 (Sheldrick, 2014), 
SHELXLE Rev714 (H\"ubschle et al., 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
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_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type
'Rigaku Rapid II curved image plate diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0165
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_diffrn_reflns_limit_h_max       26
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_diffrn_reflns_limit_l_max       23
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_diffrn_reflns_number            66194
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.237
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_diffrn_source                   'microfocus X-ray tube'
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            black
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_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.310
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_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.00067(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     511
_refine_ls_number_reflns         6973
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0462P)^2^+22.5412P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1251
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6710
_reflns_number_total             6973
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1860-5397-12-182-S2.cif
_cod_data_source_block           FSE-2-70-5
_cod_depositor_comments          'Adding full bibliography for 4032050.cif.'
_cod_database_code               4032050
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.592
_shelx_estimated_absorpt_t_max   0.720
_shelx_res_checksum              2320
_shelx_hkl_checksum              84806