Conjugated Oligomers with Stable Radical Substituents: Synthesis, Single Crystal Structures, Electronic Structure, and Excited State Dynamics
Huang, Yiming; Xu, Zihao; Jin, Shijian; Li, Chenyang; Warncke, Kurt; Evangelista, Francesco A.; Lian, Tianquan; Egap, Eilaf; Chemistry of Materials 30 (2018) 7840–; doi:10.1021/acs.chemmater.8b03366

data_4003386
_publ_section_title
;
 Conjugated Oligomers with Stable Radical Substituents: Synthesis, Single
 Crystal Structures, Electronic Structure, and Excited State Dynamics
;
_journal_issue                   21
_journal_name_full               'Chemistry of Materials'
_journal_page_first              7840
_journal_paper_doi               10.1021/acs.chemmater.8b03366
_journal_volume                  30
_journal_year                    2018
_chemical_formula_moiety         '2(C11 H14 N2 O2 S)'
_chemical_formula_sum            'C22 H28 N4 O4 S2'
_chemical_formula_weight         476.60
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-09-19
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_cell_angle_alpha                67.750(3)
_cell_angle_beta                 76.075(4)
_cell_angle_gamma                70.501(3)
_cell_formula_units_Z            2
_cell_length_a                   8.6033(19)
_cell_length_b                   11.704(3)
_cell_length_c                   12.974(4)
_cell_measurement_reflns_used    2342
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.387
_cell_measurement_theta_min      2.752
_cell_volume                     1130.0(5)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX2 v2014.11 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0951
_diffrn_reflns_av_unetI/netI     0.3524
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.155
_diffrn_reflns_theta_min         1.711
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           35
_diffrn_source_voltage           45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0608 before and 0.0497 after correction.
 The Ratio of minimum to maximum transmission not present.
 The \l/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.0615 before and 0.0495 after correction.
 The Ratio of minimum to maximum transmission is 0.85.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 22483 reflections, Rint = 0.0560
 (8371 with I > 3sig(I), Rint = 0.0387)
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.359
_exptl_crystal_size_mid          0.313
_exptl_crystal_size_min          0.104
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         6044
_refine_ls_number_restraints     45
_refine_ls_restrained_S_all      0.957
_refine_ls_R_factor_all          0.1198
_refine_ls_R_factor_gt           0.0644
_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^)+(0.0736P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1496
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3432
_reflns_number_total             6044
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cm8b03366_si_002.cif
_cod_data_source_block           RA2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1129.9(5)
_cod_database_code               4003386
_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. Rigid body (RIGU) restrains
 C7, C11, C10, N2, C6, C8, C9
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C3B(H3B), C2B(H2B)
3.b Idealised Me refined as rotating group:
 C10(H10D,H10E,H10F), C9(H9A,H9B,H9C), C11B(H11A,H11B,H11C), C8B(H8BA,H8BB,
 H8BC), C10B(H10A,H10B,H10C), C11(H11D,H11E,H11F), C9B(H9BA,H9BB,H9BC), C8(H8A,
 H8B,H8C)
;
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a loop with paratone oil'
_olex2_submission_original_sample_id RA2
_olex2_submission_special_instructions 'No special instructions were received'