A donor polymer based on 3-cyanothiophene with superior batch-to-batch reproducibility for high-efficiency organic solar cells
Yuan, Xiyue; Zhao, Yunli; Zhan, Tao; Oh, Jiyeon; Zhou, Jiadong; Li, Junyu; Wang, Xiaojing; Wang, Zhiqiang; Pang, Shuting; Cai, Ping; Yang, Changduk; He, Zhicai; Xie, Zengqi; Duan, Chunhui; Huang, Fei; Cao, Yong; Energy & Environmental Science 14 (2021) 5530–5540; doi:10.1039/D1EE01957K

data_1564399
_publ_section_title
;
 A donor polymer based on 3-cyanothiophene with superior batch-to-batch
 reproducibility for high-efficiency organic solar cells
;
_journal_issue                   10
_journal_name_full               'Energy &amp; Environmental Science'
_journal_page_first              5530
_journal_page_last               5540
_journal_paper_doi               10.1039/D1EE01957K
_journal_volume                  14
_journal_year                    2021
_chemical_formula_moiety         'C29 H37 Br2 N S3'
_chemical_formula_sum            'C29 H37 Br2 N S3'
_chemical_formula_weight         655.59
_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             2021-08-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-08-18 deposited with the CCDC.	2021-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                94.993(4)
_cell_angle_beta                 108.440(4)
_cell_angle_gamma                91.696(4)
_cell_formula_units_Z            6
_cell_length_a                   13.9722(7)
_cell_length_b                   17.5232(8)
_cell_length_c                   19.1562(9)
_cell_measurement_reflns_used    5468
_cell_measurement_temperature    149.98(10)
_cell_measurement_theta_max      72.5160
_cell_measurement_theta_min      3.3860
_cell_volume                     4424.4(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_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    -13.00  89.00   0.50    7.00    --    0.00  72.00 -30.00  204
  2  \w    -40.00  12.00   0.50    7.00    --    0.00 -38.00 -60.00  104
  3  \w    -30.00   8.00   0.50    7.00    --    0.00 -57.00 120.00   76
  4  \w    -82.00 -55.00   0.50    7.00    --    0.00 -57.00 120.00   54
  5  \w    -86.00   5.00   0.50    7.00    --    0.00 -72.00 -90.00  182
  6  \w     -9.00  47.00   0.50   28.00    --    5.00  38.00 120.00  112
  7  \w    -47.00 -20.00   0.50   28.00    --  -98.80  72.00 -60.00   54
  8  \w    -89.00 -62.00   0.50   28.00    --  -98.80  72.00 -60.00   54
  9  \w   -105.00 -22.00   0.50   28.00    --  -98.80  72.00  30.00  166
 10  \w   -100.00 -74.00   0.50   28.00    --  -98.80  72.00   0.00   52
 11  \w   -112.00 -34.00   0.50   28.00    --  -98.80  72.00-180.00  156
 12  \w   -112.00  -9.00   0.50   28.00    --  -98.80  57.00 -60.00  206
 13  \w   -112.00 -10.00   0.50   28.00    --  -98.80  19.00-180.00  204
 14  \w   -112.00 -32.00   0.50   28.00    --  -98.80  72.00 120.00  160
 15  \w   -113.00 -10.00   0.50   28.00    --  -98.80  57.00  30.00  206
 16  \w    -98.00 -63.00   0.50   28.00    --  -98.80  72.00  60.00   70
 17  \w   -112.00 -12.00   0.50   28.00    --  -98.80  19.00 -90.00  200
 18  \w   -108.00 -79.00   0.50   28.00    --  -98.80  72.00 -30.00   58
 19  \w    -98.00 -56.00   0.50   28.00    --  -98.80  72.00  90.00   84
 20  \w   -112.00 -59.00   0.50   28.00    --  -98.80  72.00-150.00  106
 21  \w   -185.00-107.00   0.50   28.00    --  -98.80 -19.00-180.00  156
 22  \w   -112.00 -19.00   0.50   28.00    --  -98.80  72.00 -90.00  186
 23  \w   -112.00 -78.00   0.50   28.00    --  -98.80  72.00 150.00   68
 24  \w    -65.00 -39.00   0.50   28.00    --  -98.80  72.00 150.00   52
 25  \w   -184.00 -73.00   0.50   28.00    --  -98.80   0.00  60.00  222
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0890861000
_diffrn_orient_matrix_UB_12      0.0232917000
_diffrn_orient_matrix_UB_13      0.0711467000
_diffrn_orient_matrix_UB_21      0.0688615000
_diffrn_orient_matrix_UB_22      -0.0506531000
_diffrn_orient_matrix_UB_23      -0.0305806000
_diffrn_orient_matrix_UB_31      0.0296627000
_diffrn_orient_matrix_UB_32      0.0686183000
_diffrn_orient_matrix_UB_33      -0.0355614000
_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  0.0891
_diffrn_reflns_av_unetI/netI     0.1061
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            43246
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         2.444
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    5.603
_exptl_absorpt_correction_T_max  0.829
_exptl_absorpt_correction_T_min  0.771
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_description       plate
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.058
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.039
_refine_diff_density_max         4.679
_refine_diff_density_min         -0.828
_refine_diff_density_rms         0.181
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     952
_refine_ls_number_reflns         15307
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.1726
_refine_ls_R_factor_gt           0.0857
_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^)+(0.1461P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2003
_refine_ls_wR_factor_ref         0.2572
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7029
_reflns_number_total             15307
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ee01957k2.cif
_cod_data_source_block           1-3
_cod_depositor_comments          'Adding full bibliography for 1564399.cif.'
_cod_database_code               1564399
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C29S3N1Br2
_reflns_odcompleteness_completeness 98.45
_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. Uiso/Uaniso restraints and constraints
Uanis(C01L) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C02Y) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C026) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C00O) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
3.a Secondary CH2 refined with riding coordinates:
 C00L(H00A,H00B), C00O(H00E,H00F), C00T(H00G,H00H), C00W(H00I,H00J), C00Y(H00C,
 H00D), C011(H01S,H01T), C012(H01A,H01B), C013(H01C,H01D), C015(H01U,H01V),
 C016(H3,H), C018(H01E,H01F), C01B(H01G,H01H), C01E(H01I,H01J), C01H(H01K,H01L),
  C01I(H01M,H01N), C01J(H01W,H01X), C01K(H01Y,HA), C01L(H01Z,HB), C01P(H4,HC),
 C01Q(H01,HD), C01U(H01O,H01P), C01V(H01Q,H01R), C01W(H1,HE), C01X(H2,HF),
 C01Y(H5,HG), C020(H02A,H02B), C022(H6,HH), C024(H7,HI), C028(H02C,H02D),
 C02A(H8,HJ), C02B(H02O,H02P), C02C(H9,HK), C02D(H02Q,H02R), C02F(H02E,H02F),
 C02G(H02T,H02U), C02I(H10,HL), C02L(H02V,H02W), C02M(H11,HM), C02N(H12,HN),
 C02P(H02X,H02Y), C02S(H14,HO), C02Z(H02M,H02N)
3.b Aromatic/amide H refined with riding coordinates:
 C00P(H00P), C014(H014), C017(H017), C019(H019), C021(H021), C023(H023),
 C029(H029), C02E(H02S), C02O(H13)
3.c Idealised Me refined as rotating group:
 C02Q(H02G,H02H,H02I), C02T(H02Z,HP,HQ), C02U(H15,HR,HS), C02V(H02J,H02K,H02L),
  C02W(H16,HT,HU), C02Y(H02,HV,HW)
;
_shelx_res_checksum              8764
_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 1.615
_oxdiff_exptl_absorpt_empirical_full_min 0.433