Lactone-fused electron-deficient building blocks for n-type polymer field-effect transistors: synthesis, properties, and impact of alkyl substitution positions
Wang, Xiao-Ye; Zhang, Meng-Wen; Zhuang, Fang-Dong; Wang, Jie-Yu; Pei, Jian; Polym. Chem. 7 (2016) 2264–; doi:10.1039/C6PY00143B

data_1542533
_publ_section_title
;
 Lactone-fused electron-deficient building blocks for n-type polymer
 field-effect transistors: synthesis, properties, and impact of alkyl
 substitution positions
;
_journal_issue                   12
_journal_name_full               'Polym. Chem.'
_journal_page_first              2264
_journal_paper_doi               10.1039/C6PY00143B
_journal_volume                  7
_journal_year                    2016
_chemical_formula_moiety         'C28 H32 O4 S2'
_chemical_formula_sum            'C28 H32 O4 S2'
_chemical_formula_weight         496.65
_chemical_name_common            P662T-3H
_chemical_name_systematic
3,7-bis(3-hexylthiophen-2-yl)pyrano[4,3-c]pyran-1,5-dione
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-08-03
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_audit_update_record
;
2015-12-25 deposited with the CCDC.
2016-02-18 downloaded from the CCDC.
;
_cell_angle_alpha                94.625(6)
_cell_angle_beta                 94.955(9)
_cell_angle_gamma                95.942(7)
_cell_formula_units_Z            1
_cell_length_a                   6.0485(7)
_cell_length_b                   6.9813(4)
_cell_length_c                   15.2806(16)
_cell_measurement_reflns_used    927
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      26.7130
_cell_measurement_theta_min      3.7570
_cell_volume                     636.76(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      180.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9948
_diffrn_measured_fraction_theta_max 0.8235
_diffrn_measurement_details
;
  1 omega  -12.00   75.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017   57.0000    0.0000 87

  2 omega  -84.00   12.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.5610  -57.0000   60.0000 96

  3 omega  -34.00   55.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.5610   57.0000 -150.0000 89
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0409183000
_diffrn_orient_matrix_UB_12      -0.0083065000
_diffrn_orient_matrix_UB_13      0.0418103000
_diffrn_orient_matrix_UB_21      -0.1107131000
_diffrn_orient_matrix_UB_22      -0.0000397000
_diffrn_orient_matrix_UB_23      -0.0195548000
_diffrn_orient_matrix_UB_31      -0.0098543000
_diffrn_orient_matrix_UB_32      -0.1022314000
_diffrn_orient_matrix_UB_33      -0.0076328000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0838
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4143
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         2.946
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.08095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       needle
_exptl_crystal_F_000             264
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CHCl3/MeOH'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.830
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2507
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1171
_refine_ls_R_factor_gt           0.0745
_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^)+(0.0961P)^2^+0.5384P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1791
_refine_ls_wR_factor_ref         0.2069
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1647
_reflns_number_total             2507
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6py00143b2.cif
_cod_data_source_block           exp_3932
_cod_depositor_comments          'Adding full bibliography for 1542533.cif.'
_cod_original_cell_volume        636.77(10)
_cod_database_code               1542533
_chemical_oxdiff_formula         'C24 H48 O4 S2'
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_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.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C11(H11)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.953
_shelxl_version_number           2013-3