Multifaceted Regioregular Oligo(thieno[3,4-b]thiophene)s Enabled by Tunable Quinoidization and Reduced Energy Band Gap.
Liu, Feng; Espejo, Guzmán L; Qiu, Shuhai; Oliva, María Moreno; Pina, João; Seixas de Melo, J Sérgio; Casado, Juan; Zhu, Xiaozhang; Journal of the American Chemical Society 137 (2015) 10357–10366; doi:10.1021/jacs.5b05940

data_4129450
_publ_section_title
;
 Multifaceted Regioregular Oligo(thieno[3,4-b]thiophene)s Enabled by
 Tunable Quinoidization and Reduced Energy Band Gap.
;
_journal_issue                   32
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10357
_journal_page_last               10366
_journal_paper_doi               10.1021/jacs.5b05940
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C18 H14 O4 S4'
_chemical_formula_sum            'C18 H14 O4 S4'
_chemical_formula_weight         422.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.903(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.053(2)
_cell_length_b                   10.020(5)
_cell_length_c                   17.645(9)
_cell_measurement_reflns_used    2642
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4466
_cell_measurement_theta_min      2.0325
_cell_volume                     893.3(7)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 45.0886
	          2theta: -20.2423
scan:
	Number of images: 270
	           Slice: -110.0000 - 25.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 45.0886
	          2theta: -20.2423
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0123
_diffrn_orient_matrix_UB_12      0.1942
_diffrn_orient_matrix_UB_13      0.0366
_diffrn_orient_matrix_UB_21      -0.0980
_diffrn_orient_matrix_UB_22      0.0093
_diffrn_orient_matrix_UB_23      -0.0165
_diffrn_orient_matrix_UB_31      -0.0101
_diffrn_orient_matrix_UB_32      -0.0088
_diffrn_orient_matrix_UB_33      0.0551
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5843
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.446
_diffrn_reflns_theta_min         2.309
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.554
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_description       rod
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.724
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.190
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.232
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2028
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.221
_refine_ls_R_factor_all          0.1029
_refine_ls_R_factor_gt           0.0959
_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^)+(0.0958P)^2^+6.0795P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2680
_refine_ls_wR_factor_ref         0.2792
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1904
_reflns_number_total             2028
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b05940_si_002.cif
_cod_data_source_block           sa3950
_cod_original_cell_volume        893.2(7)
_cod_database_code               4129450
_diffrn_number_total             2157
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
S1A \\sim C5 \\sim C5A \\sim S1: within 1.7A with sigma of 0.02 and sigma for
terminal atoms of 0.04
Uanis(S1A) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C5A) \\sim Ueq, Uanis(S1)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Sof(S1A)=Sof(C5A)=Sof(H5A)=1-FVAR(1)
 Sof(S1)=Sof(C5)=Sof(H5)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C5A(H5A)
4.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              61246
_shelx_hkl_checksum              2778
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'