Synthesis and charge-transport properties of novel π-conjugated polymers incorporating core-extended naphtho[2,1-b:3,4-b′]dithiophene diimides
Zhao, Lingli; Cao, Yanyan; Qin, Hanwen; He, Xi; Zhao, Zhiyuan; Guo, Yunlong; Chen, Huajie; Polymer Chemistry 15 (2024) 59–70; doi:10.1039/D3PY01186K

data_1570411
_publ_section_title
;
 Synthesis and charge-transport properties of novel \p-conjugated polymers
 incorporating core-extended naphtho[2,1-b:3,4-b&#x2032;]dithiophene
 diimides
;
_journal_issue                   2
_journal_name_full               'Polymer Chemistry'
_journal_page_first              59
_journal_page_last               70
_journal_paper_doi               10.1039/D3PY01186K
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C28 H24 Br2 N2 O4 S2'
_chemical_formula_sum            'C28 H24 Br2 N2 O4 S2'
_chemical_formula_weight         676.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2023-10-22
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-10-23 deposited with the CCDC.	2023-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.6555(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.37851(9)
_cell_length_b                   22.32456(14)
_cell_length_c                   7.70669(5)
_cell_measurement_reflns_used    16078
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      71.3220
_cell_measurement_theta_min      2.8800
_cell_volume                     2644.74(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -40.00  69.00   0.50    0.50    --   42.30 -57.00  90.00  218
  2  \w     -5.00  28.00   0.50    0.50    --   42.30 -82.00-120.00   66
  3  \w     83.00 131.00   0.50    0.50    --   42.30  77.00 -30.00   96
  4  \w    -19.00  50.00   0.50    0.50    --   42.30 -57.00 -60.00  138
  5  \w    -30.00  82.00   0.50    0.50    --   42.30 -82.00 -90.00  224
  6  \w    -26.00  85.00   0.50    0.50    --   42.30 -82.00  60.00  222
  7  \w     84.00 121.00   0.50    0.50    --   42.30  77.00   0.00   74
  8  \w     12.00 191.00   0.50    0.66    --  101.60 -12.00 -90.00  358
  9  \w     18.00  44.00   0.50    0.66    --  101.60 -82.00 -30.00   52
 10  \w     99.00 129.00   0.50    0.66    --  101.60 -82.00-120.00   60
 11  \w     67.00 139.00   0.50    0.66    --  101.60 -82.00 -30.00  144
 12  \w     40.00 122.00   0.50    0.66    --  101.60 -82.00 150.00  164
 13  \w     91.00 117.00   0.50    0.66    --  101.60 -82.00 -60.00   52
 14  \w     54.00  93.00   0.50    0.66    --  101.60  38.00-180.00   78
 15  \w     12.00  95.00   0.50    0.66    --  101.60 -82.00-120.00  166
 16  \w     38.00  78.00   0.50    0.66    --  101.60 -38.00 150.00   80
 17  \w     88.00 133.00   0.50    0.66    --  101.60 -50.00-150.00   90
 18  \w     90.00 116.00   0.50    0.66    --  101.60 -63.00   0.00   52
 19  \w     13.00  80.00   0.50    0.66    --  101.60 -63.00   0.00  134
 20  \w    104.00 149.00   0.50    0.66    --  101.60 -38.00 150.00   90
 21  \w     91.00 142.00   0.50    0.66    --  101.60 -82.00  90.00  102
 22  \w     99.00 160.00   0.50    0.66    --  101.60  38.00-180.00  122
 23  \w     35.00 118.00   0.50    0.66    --  101.60 -82.00  60.00  166
 24  \w     34.00  67.00   0.50    0.66    --  101.60 -50.00-150.00   66
 25  \w     80.00 122.00   0.50    0.66    --  101.60 -82.00  30.00   84
 26  \w     14.00  39.00   0.50    0.66    --  101.60 -82.00-150.00   50
 27  \w     85.00 139.00   0.50    0.66    --  101.60 -82.00-150.00  108
 28  \w     53.00 137.00   0.50    0.66    --  101.60 -82.00 -90.00  168
 29  \w     20.00 161.00   0.50    0.66    --  101.60 -25.00   0.00  282
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0980281000
_diffrn_orient_matrix_UB_12      -0.0138605000
_diffrn_orient_matrix_UB_13      0.0042609000
_diffrn_orient_matrix_UB_21      -0.0180120000
_diffrn_orient_matrix_UB_22      0.0651271000
_diffrn_orient_matrix_UB_23      0.0542446000
_diffrn_orient_matrix_UB_31      -0.0102665000
_diffrn_orient_matrix_UB_32      0.0180554000
_diffrn_orient_matrix_UB_33      -0.1925361000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            25803
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         2.875
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.692
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.626
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.00015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         4680
_refine_ls_number_restraints     45
_refine_ls_restrained_S_all      1.166
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0271
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0356P)^2^+2.1226P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0732
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4403
_reflns_number_total             4680
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3py01186k2.cif
_cod_data_source_block           y5_2
_cod_depositor_comments          'Adding full bibliography for 1570411.cif.'
_cod_database_code               1570411
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.573
_shelx_estimated_absorpt_t_min   0.503
_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. Restrained distances
 C25B-C24B = C25B-C26B
 1.54 with sigma of 0.01
 Br1-C1
 1.5 with sigma of 0.01
 C24B-C25 \\sim C24B-C25B
 with sigma of 0.02
 C24B-C26B \\sim C24B-C26
 with sigma of 0.04
 C27B-C25 \\sim C27B-C25B
 with sigma of 0.02
 C24-C25 \\sim C24-C25B
 with sigma of 0.02
 C24-C26B \\sim C24-C26
 with sigma of 0.04
 C26B-C25 \\sim C26-C25B
 with sigma of 0.02
 C27B-C26B \\sim C27B-C26
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 C24, C25, C26, C27, C28
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C24B, C25B, C26B, C27B, C28B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Others
 Sof(Br3)=Sof(C24B)=Sof(H24B)=Sof(C25B)=Sof(H25C)=Sof(H25D)=Sof(C26B)=
 Sof(H26D)=Sof(H26E)=Sof(H26F)=Sof(C27B)=Sof(H27C)=Sof(H27D)=Sof(C28B)=
 Sof(H28D)=Sof(H28E)=Sof(H28F)=1-FVAR(1)
 Sof(Br2)=Sof(C24)=Sof(H24)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(C26)=Sof(H26A)=
 Sof(H26B)=Sof(H26C)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(C28)=Sof(H28A)=Sof(H28B)=
 Sof(H28C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C19(H19), C24(H24), C24B(H24B)
5.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C22(H22A,H22B), C25(H25A,H25B), C25B(H25C,H25D), C27(H27A,
 H27B), C27B(H27C,H27D)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9)
5.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C26(H26A,H26B,H26C), C26B(H26D,H26E,
 H26F), C28(H28A,H28B,H28C), C28B(H28D,H28E,H28F)
;
_shelx_res_checksum              59182
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.778
_oxdiff_exptl_absorpt_empirical_full_min 0.682