Central dicyanomethylene-substituted unsymmetrical squaraines and their application in organic solar cells
Wu, Jianglin; Yang, Daobin; Wang, Qingfen; Yang, Lin; Sasabe, Hisahiro; Sano, Takeshi; Kido, Junji; Lu, Zhiyun; Huang, Yan; Journal of Materials Chemistry A 6 (2018) 5797–; doi:10.1039/C8TA00750K

data_7237116
_publ_section_title
;
 Central dicyanomethylene-substituted unsymmetrical squaraines and their
 application in organic solar cells
;
_journal_issue                   14
_journal_name_full               'Journal of Materials Chemistry A'
_journal_page_first              5797
_journal_paper_doi               10.1039/C8TA00750K
_journal_volume                  6
_journal_year                    2018
_chemical_formula_moiety         'C33 H36 N4 O2 S'
_chemical_formula_sum            'C33 H36 N4 O2 S'
_chemical_formula_weight         552.72
_chemical_melting_point          500
_chemical_name_systematic
4-((3-Butylbenzo[d]thiazol-3-ium-2-yl)methylene)-2-(4-(dibutylamino)-2-hydroxyphenyl)-3-(dicyanomethylene)-cyclobut-1-enolate
_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             2016-10-28
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2018-01-09 deposited with the CCDC.
2018-02-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.910(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9009(5)
_cell_length_b                   29.0765(17)
_cell_length_c                   11.7440(6)
_cell_measurement_reflns_used    4884
_cell_measurement_temperature    143.00(10)
_cell_measurement_theta_max      28.9260
_cell_measurement_theta_min      3.4210
_cell_volume                     2923.0(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      143.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -83.00  -57.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  174.0000  -54.0000 26

  2 omega  -49.00  -24.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  114.0000  165.0000 25

  3 omega   16.00   41.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       16.6856 -114.0000   75.0000 25

  4 omega   39.00   64.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  174.0000  -54.0000 25

  5 omega  -23.00   24.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000 -120.0000 47

  6 omega  -87.00  -37.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669 -178.0000  -90.0000 50

  7 omega  -79.00  -46.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -57.0000 -120.0000 33

  8 omega  -35.00    2.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -57.0000 -120.0000 37

  9 omega    1.00   62.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   57.0000  120.0000 61

 10 omega    0.00   84.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   57.0000  -90.0000 84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0045841000
_diffrn_orient_matrix_UB_12      0.0120582000
_diffrn_orient_matrix_UB_13      -0.0533293000
_diffrn_orient_matrix_UB_21      -0.0183740000
_diffrn_orient_matrix_UB_22      -0.0208195000
_diffrn_orient_matrix_UB_23      -0.0322900000
_diffrn_orient_matrix_UB_31      -0.0807055000
_diffrn_orient_matrix_UB_32      0.0040507000
_diffrn_orient_matrix_UB_33      -0.0073029000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25400
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.920
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1176
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-Hexane/CH2Cl2'
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5961
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0925
_refine_ls_R_factor_gt           0.0632
_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^)+(0.0522P)^2^+1.9416P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1387
_refine_ls_wR_factor_ref         0.1552
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4256
_reflns_number_total             5961
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ta00750k2.cif
_cod_data_source_block           161027_s1_wjl
_cod_database_code               7237116
_chemical_oxdiff_formula         c12h12n2o2
_reflns_odcompleteness_completeness 99.77
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C26(H26A,H26B), C27(H27A,H27B),
 C28(H28A,H28B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C12(H12), C22(H22), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C29(H29A,H29B,H29C), C33(H33A,H33B,H33C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'