Bromination of the Small-Molecule Acceptor with Fixed Position for High-Performance Solar Cells
Qu, Jianfei; Li, Duning; Wang, Huan; Zhou, Jiadong; Zheng, Nan; Lai, Hanjian; Liu, Tao; Xie, Zengqi; He, Feng; Chemistry of Materials 31 (2019) 8044–; doi:10.1021/acs.chemmater.9b02501

data_4002986
_publ_section_title
;
 Bromination of the Small-Molecule Acceptor with Fixed Position for
 High-Performance Solar Cells
;
_journal_issue                   19
_journal_name_full               'Chemistry of Materials'
_journal_page_first              8044
_journal_paper_doi               10.1021/acs.chemmater.9b02501
_journal_volume                  31
_journal_year                    2019
_chemical_formula_moiety         'C94 H80 Br2 N4 O2 S4'
_chemical_formula_sum            'C94 H80 Br2 N4 O2 S4'
_chemical_formula_weight         1585.68
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.617(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.8869(13)
_cell_length_b                   18.505(3)
_cell_length_c                   27.6655(15)
_cell_measurement_reflns_used    5340
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      70.0510
_cell_measurement_theta_min      2.9120
_cell_volume                     7936.9(15)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (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      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_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  88.00   0.50    6.00    --    0.00  38.00 -30.00  204
  2  \w    -38.00 -11.00   0.50    6.00    --    0.00 -19.00  30.00   54
  3  \w     -7.00  50.00   0.50    6.00    --    0.00  72.00 150.00  114
  4  \w    -83.00 -41.00   0.50   24.00    --    5.00 -72.00  90.00   84
  5  \w   -188.00-113.00   0.50   24.00    --  -98.80 -19.00 -30.00  150
  6  \w    -98.00 -61.00   0.50   24.00    --  -98.80  72.00 -90.00   74
  7  \w   -188.00 -88.00   0.50   24.00    --  -98.80 -72.00 120.00  200
  8  \w   -111.00 -75.00   0.50   24.00    --  -98.80  72.00-180.00   72
  9  \w   -110.00 -16.00   0.50   24.00    --  -98.80  38.00-120.00  188
 10  \w   -175.00-148.00   0.50   24.00    --  -98.80 -19.00 -60.00   54
 11  \w   -117.00 -87.00   0.50   24.00    --  -98.80 -19.00 -60.00   60
 12  \w    -40.00 -15.00   0.50   24.00    --  -98.80  72.00 -90.00   50
 13  \w   -102.00 -54.00   0.50   24.00    --  -98.80  72.00-120.00   96
 14  \w   -112.00 -10.00   0.50   24.00    --  -98.80  57.00-120.00  204
 15  \w   -113.00 -23.00   0.50   24.00    --  -98.80  19.00 120.00  180
;
_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      -0.0392784000
_diffrn_orient_matrix_UB_12      -0.0764645000
_diffrn_orient_matrix_UB_13      -0.0054080000
_diffrn_orient_matrix_UB_21      0.0454332000
_diffrn_orient_matrix_UB_22      -0.0155969000
_diffrn_orient_matrix_UB_23      -0.0427200000
_diffrn_orient_matrix_UB_31      0.0791605000
_diffrn_orient_matrix_UB_32      -0.0289337000
_diffrn_orient_matrix_UB_33      0.0374621000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1244
_diffrn_reflns_av_unetI/netI     0.1372
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            32705
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         2.895
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       plate
_exptl_crystal_F_000             3288
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.641
_refine_diff_density_min         -1.225
_refine_diff_density_rms         0.158
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.252
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     959
_refine_ls_number_reflns         13544
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.254
_refine_ls_R_factor_all          0.2461
_refine_ls_R_factor_gt           0.1310
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3258
_refine_ls_wR_factor_ref         0.4238
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5775
_reflns_number_total             13544
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cm9b02501_si_002.cif
_cod_data_source_block           ITIC-2Br
_cod_original_cell_volume        7937.0(14)
_cod_database_code               4002986
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 96.31
_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. Restrained distances
 C02Y-C02X = C02X-C02Q
 1.54 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C017(H01A,H01B), C01M(H01D,H01H), C01U(H01K,H01M), C01X(H01N,H01O), C01Y(H01Q,
 H01R), C020(H02A,H02B), C024(H02C,H02D), C026(H02E,H02F), C028(H02G,H02H),
 C029(H02I,H02J), C02E(H02M,H02N), C02L(H02Q,H02R), C02M(H02S,H02T), C02N(H02U,
 H02V), C02O(H02W,H02X), C02Q(H02Y,H), C02R(H02Z,HA), C02T(H0AA,HD), C02X(H4AA,
 HK), C02Y(H5AA,HL)
3.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00F(H00F), C00G(H00G), C00K(H00K), C00N(H00N), C00P(H00P),
 C00R(H00R), C00T(H00T), C00U(H00U), C00Z(H00Z), C016(H016), C019(H019),
 C01B(H01C), C01E(H01E), C01F(H01F), C01G(H01G), C01I(H01I), C01J(H01J),
 C01L(H01L), C01P(H01P), C01S(H01S), C022(H022), C023(H023), C025(H025),
 C02A(H02K), C02B(H02L), C02H(H02O), C02J(H02P)
3.c Idealised Me refined as rotating group:
 C02S(H02,HB,HC), C02U(H1AA,HE,HF), C02V(H2AA,HG,HH), C02W(H3AA,HI,HJ)
;
_shelx_res_checksum              45225
_shelx_hkl_checksum              79425
_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 3.973
_oxdiff_exptl_absorpt_empirical_full_min 0.376