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_4029949
_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 H20 N2 S2'
_chemical_formula_sum            'C28 H20 N2 S2'
_chemical_formula_weight         448.58
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2013-09-23
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                72.675(7)
_cell_angle_beta                 86.768(8)
_cell_angle_gamma                88.228(8)
_cell_formula_units_Z            1
_cell_length_a                   5.516(2)
_cell_length_b                   9.667(4)
_cell_length_c                   11.016(4)
_cell_measurement_reflns_used    4921
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      25.389
_cell_measurement_theta_min      2.215
_cell_volume                     559.8(4)
_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      90.0(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6821
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.315
_diffrn_reflns_theta_min         1.939
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1092 before and 0.0742 after correction.
The Ratio of minimum to maximum transmission is 0.6798.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_F_000             234
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.761
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2031
_refine_ls_number_restraints     204
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0805
_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^)+(0.0452P)^2^+2.8172P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1965
_refine_ls_wR_factor_ref         0.2042
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1691
_reflns_number_total             2031
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo501630f_si_003.cif
_cod_data_source_block           rh115_a
_cod_depositor_comments
'Adding full bibliography for 4029948--4029954.cif.'
_cod_database_code               4029949
_shelxl_version_number           2013-3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.1 and sigma
for terminal atoms of 0.2
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14)
;
_shelx_res_checksum              56349
_shelx_hkl_checksum              44381