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_7237115
_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         'C30 H36 N2 O3 S'
_chemical_formula_sum            'C30 H36 N2 O3 S'
_chemical_formula_weight         504.67
_chemical_melting_point          395.5
_chemical_name_systematic
'4-((3-Butylbenzo[d]thiazol-3-ium-2-yl)methylene)-2-(4-(dibutylamino)-2-hydroxyphenyl)-3-oxocyclobut-1-enolate '
_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     iterative
_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                86.875(10)
_cell_angle_beta                 85.566(9)
_cell_angle_gamma                66.162(11)
_cell_formula_units_Z            2
_cell_length_a                   9.3736(9)
_cell_length_b                   9.8299(12)
_cell_length_c                   16.506(2)
_cell_measurement_reflns_used    1957
_cell_measurement_temperature    143.00(10)
_cell_measurement_theta_max      25.4330
_cell_measurement_theta_min      3.3310
_cell_volume                     1386.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_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 0.993
_diffrn_measured_fraction_theta_max 0.992
_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    -32.00  53.40   0.70   15.00    --  -15.44  38.00   0.00  122
  2  \w    -29.00  51.50   0.70   15.00    --  -15.44  38.00 120.00  115
  3  \w    -23.00  23.90   0.70   15.00    --  -15.44 -99.00 120.00   67
  4  \w    -19.00  20.20   0.70   15.00    --  -15.44 -99.00   0.00   56
  5  \w    -24.00  21.50   0.70   15.00    --  -15.44 -99.00-120.00   65
  6  \w    -50.00 -22.00   0.70   15.00    --  -15.44 -38.00-180.00   40
  7  \w    -40.00  49.60   0.70   15.00    --  -15.44  19.00 -90.00  128
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0213116000
_diffrn_orient_matrix_UB_12      -0.0618511000
_diffrn_orient_matrix_UB_13      0.0276208000
_diffrn_orient_matrix_UB_21      -0.0272705000
_diffrn_orient_matrix_UB_22      0.0490058000
_diffrn_orient_matrix_UB_23      0.0330797000
_diffrn_orient_matrix_UB_31      -0.0753067000
_diffrn_orient_matrix_UB_32      -0.0003599000
_diffrn_orient_matrix_UB_33      -0.0012902000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0973
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10174
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.314
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             540
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH3OH/CH2Cl2'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         5642
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1962
_refine_ls_R_factor_gt           0.1294
_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^)+7.2292P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2143
_refine_ls_wR_factor_ref         0.2434
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3258
_reflns_number_total             5642
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ta00750k2.cif
_cod_data_source_block           1
_cod_original_cell_volume        1386.6(3)
_cod_database_code               7237115
_chemical_oxdiff_formula         c12h12n2o2s1
_reflns_odcompleteness_completeness 99.40
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C29-C30 = C29-C30A
 1.51 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C30) = Uanis(C30A)
4. Others
 Sof(H29C)=Sof(H29D)=Sof(C30A)=Sof(H30D)=Sof(H30E)=Sof(H30F)=1-FVAR(1)
 Sof(H29A)=Sof(H29B)=Sof(C30)=Sof(H30C)=Sof(H30A)=Sof(H30B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C23(H23A,H23B), C24(H24A,H24B),
 C25(H25A,H25B), C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B), C29(H29C,H29D)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5), C12(H12), C19(H19), C21(H21), C22(H22)
5.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C26(H26A,H26B,H26C), C30(H30C,H30A,H30B), C30A(H30D,H30E,
 H30F)
5.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_shelxl_version_number     2014/7
_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 1.580
_oxdiff_exptl_absorpt_empirical_full_min 0.593