Pyrazine-Fused Isoindigo: A New Building Block for Polymer Solar Cells with High Open Circuit Voltage
Zhang, Haoli; Li, Jiu-Long; Chai, Yunfei; Wang, Wei Vanessa; Shi, Zi-Fa; Xu, Zhu-Guo; Chem. Commun.  (2017) –; doi:10.1039/C7CC01973D

data_7120100
_publ_section_title
;
 Pyrazine-Fused Isoindigo: A New Building Block for Polymer Solar Cells
 with High Open Circuit Voltage
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC01973D
_journal_year                    2017
_chemical_formula_moiety         'C19 H22 Br N2 O, C H Cl3'
_chemical_formula_sum            'C20 H23 Br Cl3 N2 O'
_chemical_formula_weight         493.66
_chemical_name_common            BrPzIIG
_chemical_name_systematic
(3E,3'E)-3,3'-(pyrazine-2,5-diylbis(methanylylidene))bis(6-bromo-1-octylindolin-2-one)
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-05-07
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_audit_update_record
;
2017-02-24 deposited with the CCDC.
2017-05-04 downloaded from the CCDC.
;
_cell_angle_alpha                97.479(11)
_cell_angle_beta                 93.857(10)
_cell_angle_gamma                93.049(12)
_cell_formula_units_Z            2
_cell_length_a                   4.9228(7)
_cell_length_b                   11.6856(18)
_cell_length_c                   19.2004(19)
_cell_measurement_reflns_used    1265
_cell_measurement_temperature    295.35(10)
_cell_measurement_theta_max      23.0610
_cell_measurement_theta_min      3.5170
_cell_volume                     1090.5(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.35(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   21.00   48.00   1.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9916   77.0000  -60.0000 18

  2 omega   23.00   50.00   1.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9916   77.0000 -180.0000 18

  3 omega   23.00   48.50   1.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9916   77.0000   60.0000 17

  4 omega   -8.00   82.00   1.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4291   77.0000   60.0000 60

  5 omega   -8.00   80.50   1.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4291   77.0000  -60.0000 59

  6 omega  -10.00   80.00   1.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4291   77.0000 -180.0000 60

  7 omega  -43.00  -16.00   1.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9916   77.0000   60.0000 18
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0623876000
_diffrn_orient_matrix_UB_12      0.0257213000
_diffrn_orient_matrix_UB_13      0.0299116000
_diffrn_orient_matrix_UB_21      -0.0250604000
_diffrn_orient_matrix_UB_22      -0.0553573000
_diffrn_orient_matrix_UB_23      0.0104972000
_diffrn_orient_matrix_UB_31      0.1281257000
_diffrn_orient_matrix_UB_32      0.0060363000
_diffrn_orient_matrix_UB_33      0.0197795000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.1327
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7268
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.46
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.265
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86547
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             502
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4277
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.1194
_refine_ls_R_factor_gt           0.0637
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0217P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.1165
_reflns_number_gt                2585
_reflns_number_total             4277
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc01973d2.cif
_cod_data_source_block           lijiul0506
_cod_database_code               7120100
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Others
 Fixed Sof: H20(0.75) H20A(0.25) Cl1(0.75) Cl3(0.75) Cl1'(0.25) Cl2'(0.25)
3.a Ternary CH refined with riding coordinates:
 C20(H20), C20(H20A)
3.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,
 H16B), C17(H17A,H17B), C18(H18A,H18B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C6(H6), C7(H7), C9(H9)
3.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_olex2_date_sample_data_collection 2015-05-06
_olex2_submission_special_instructions 'No special instructions were received'