Enhancing Polymer Photovoltaic Performance via Optimized Intramolecular Ester-Based Noncovalent Sulfur···Oxygen Interactions
Chen, Jianhua; Liao, Qiaogan; Wang, Gang; Yan, Zhenglong; Wang, Hang; Wang, Yulun; Zhang, Xianhe; Tang, Yumin; Facchetti, Antonio; Marks, Tobin J.; Guo, Xugang; Macromolecules 51 (2018) 3874–; doi:10.1021/acs.macromol.8b00161

data_1552814
_publ_section_title
;
 Enhancing Polymer Photovoltaic Performance via Optimized Intramolecular
 Ester-Based Noncovalent Sulfur&#x00B7;&#x00B7;&#x00B7;Oxygen Interactions
;
_journal_issue                   10
_journal_name_full               Macromolecules
_journal_page_first              3874
_journal_paper_doi               10.1021/acs.macromol.8b00161
_journal_volume                  51
_journal_year                    2018
_chemical_formula_moiety         'C31 H50 Br2 O S2'
_chemical_formula_sum            'C31 H50 Br2 O S2'
_chemical_formula_weight         662.65
_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             2017-07-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                88.875(5)
_cell_angle_beta                 89.662(5)
_cell_angle_gamma                72.188(6)
_cell_formula_units_Z            2
_cell_length_a                   5.5012(4)
_cell_length_b                   7.6825(6)
_cell_length_c                   38.8500(17)
_cell_measurement_reflns_used    2763
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4400
_cell_measurement_theta_min      6.0320
_cell_volume                     1562.91(19)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.966
_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     14.00  89.00   1.00    1.00    --   40.21  37.00  90.00   75
  2  \w     50.00 122.00   1.00    1.00    --  107.48 -45.00 -30.00   72
  3  \w     83.00 178.00   1.00    1.00    --  107.48  30.00  30.00   95
  4  \w    123.00 175.00   1.00    1.00    --  107.48  77.00 -30.00   52
  5  \w    109.00 178.00   1.00    1.00    --  107.48 111.00-120.00   69
  6  \w    121.00 151.00   1.00    1.00    --  107.48 178.00-120.00   30
  7  \w     79.00 106.00   1.00    1.00    --  107.48 178.00-120.00   27
  8  \w     76.00 111.00   1.00    1.00    --  107.48  77.00 -30.00   35
  9  \w     84.00 168.00   1.00    1.00    --  107.48  45.00 -60.00   84
 10  \w    100.00 169.00   1.00    1.00    --  107.48 111.00  30.00   69
 11  \w     62.00 116.00   1.00    1.00    --   40.21  37.00-180.00   54
 12  \w     30.00  81.00   1.00    1.00    --  107.48 -94.00 -30.00   51
 13  \w     64.00 109.00   1.00    1.00    --  107.48 -94.00   0.00   45
 14  \w     45.00  96.00   1.00    1.00    --   40.21-125.00 -60.00   51
 15  \w     35.00 106.00   1.00    1.00    --  107.48 -94.00-120.00   71
 16  \w     43.00 104.00   1.00    1.00    --  107.48-111.00-150.00   61
 17  \w    -58.00  -4.00   1.00    1.00    --  -40.21 125.00 -90.00   54
 18  \w   -100.00 -16.00   1.00    1.00    --  -40.21 -77.00 120.00   84
 19  \w   -114.00 -71.00   1.00    1.00    --  -40.21-134.00 119.00   43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0556478000
_diffrn_orient_matrix_UB_12      -0.0673816000
_diffrn_orient_matrix_UB_13      -0.0353033000
_diffrn_orient_matrix_UB_21      -0.1113404000
_diffrn_orient_matrix_UB_22      -0.1389920000
_diffrn_orient_matrix_UB_23      0.0180687000
_diffrn_orient_matrix_UB_31      -0.2665042000
_diffrn_orient_matrix_UB_32      0.1432477000
_diffrn_orient_matrix_UB_33      -0.0001827000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0795
_diffrn_reflns_av_unetI/netI     0.0796
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            10259
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.635
_diffrn_reflns_theta_min         4.553
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.692
_exptl_absorpt_correction_T_max  0.597
_exptl_absorpt_correction_T_min  0.477
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       block
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.168
_refine_diff_density_min         -0.868
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.334
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         6085
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.332
_refine_ls_R_factor_all          0.1309
_refine_ls_R_factor_gt           0.0915
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0241P)^2^+8.7213P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1863
_refine_ls_wR_factor_ref         0.2049
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3400
_reflns_number_total             6085
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ma8b00161_si_003.cif
_cod_data_source_block           exp_698
_cod_database_code               1552814
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.626
_shelx_estimated_absorpt_t_min   0.486
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Rigid bond restraints
 C4, C5
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C7, C6, C20
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C5, C6
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C22, C21
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C6, C20
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C4 \\sim C5: within 2A with sigma of 0.002 and sigma for terminal atoms of 0.004
C7 \\sim C6 \\sim C20: within 2A with sigma of 0.005 and sigma for terminal
atoms of 0.01
C5 \\sim C6: within 2A with sigma of 0.001 and sigma for terminal atoms of 0.002
C22 \\sim C21: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002
C6 \\sim C20: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002
4.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C9(H9A,H9B), C10(H10A,H10B), C17(H17A,H17B), C15(H15A,H15B),
 C18(H18A,H18B), C22(H22A,H22B), C14(H14A,H14B), C12(H12A,H12B), C11(H11A,H11B),
  C16(H16A,H16B), C25(H25A,H25B), C23(H23A,H23B), C27(H27A,H27B), C13(H13A,
 H13B), C24(H24A,H24B), C28(H28A,H28B), C29(H29A,H29B), C26(H26A,H26B),
 C30(H30A,H30B), C21(H21A,H21B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7)
4.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C31(H31A,H31B,H31C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
;
_oxdiff_exptl_absorpt_empirical_full_max 2.565
_oxdiff_exptl_absorpt_empirical_full_min 0.647