Synthesis and photophysics of thioindigo diimines and related compounds.
Boice, Geneviève; Patrick, Brian O.; McDonald, Robert; Bohne, Cornelia; Hicks, Robin; The Journal of organic chemistry 79 (2014) 9196–9205; doi:10.1021/jo501630f

data_4029954
_publ_section_title
;
 Synthesis and photophysics of thioindigo diimines and related compounds.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9196
_journal_page_last               9205
_journal_paper_doi               10.1021/jo501630f
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C28 H18 N2 S2'
_chemical_formula_sum            'C28 H18 N2 S2'
_chemical_formula_weight         446.56
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2013-10-02
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.5364(8)
_cell_length_b                   5.4027(2)
_cell_length_c                   18.7745(9)
_cell_measurement_reflns_used    6154
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      66.38
_cell_measurement_theta_min      4.31
_cell_volume                     2083.07(15)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      90.15
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10315
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.513
_diffrn_reflns_theta_min         4.306
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.461
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1144 before and 0.0552 after correction.
The Ratio of minimum to maximum transmission is 0.8067.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       needle
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.17(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         2402
_refine_ls_number_restraints     90
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0502P)^2^+0.7809P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0879
_reflns_Friedel_coverage         0.933
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                2273
_reflns_number_total             2402
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo501630f_si_005.cif
_cod_data_source_block           rh117
_cod_depositor_comments
'Adding full bibliography for 4029948--4029954.cif.'
_cod_database_code               4029954
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.952
_shelx_estimated_absorpt_t_min   0.298
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C4'(H4'), C5(H5), C5'(H5'), C6(H6), C6'(H6'), C7(H7), C7'(H7'),
 C10(H10), C10'(H10'), C11(H11), C11'(H11'), C12(H12), C12'(H12'), C13(H13),
 C13'(H13'), C14(H14), C14'(H14')
;
_shelx_res_checksum              62133
_shelx_hkl_checksum              27680