Effects of different types of unsymmetrical squaraines on the material properties and Coulomb interactions in organic photovoltaic devices
Yang, Lin; Yang, Daobin; Chen, Yao; Wu, Jianglin; Lu, Zhiyun; Sasabe, Hisahiro; Kido, Junji; Sano, Takeshi; Huang, Yan; Materials Chemistry Frontiers 2 (2018) 2116–; doi:10.1039/C8QM00327K

data_1554227
_publ_section_title
;
 Effects of different types of unsymmetrical squaraines on the material
 properties and Coulomb interactions in organic photovoltaic devices
;
_journal_issue                   11
_journal_name_full               'Materials Chemistry Frontiers'
_journal_page_first              2116
_journal_paper_doi               10.1039/C8QM00327K
_journal_volume                  2
_journal_year                    2018
_chemical_formula_moiety         'C39 H34 N2 O4'
_chemical_formula_sum            'C39 H34 N2 O4'
_chemical_formula_weight         594.68
_chemical_melting_point          508.0(10)
_chemical_name_systematic
2-(2,6-dihydroxy-4-(1,2,3,3a-tetrahydrocyclopenta[b]indol-4(8bH)-yl)phenyl)-4-(4-p-tolyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indol-7-yl)cyclobuta-1,3-diene-1,3-bis(olate)
_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             2016-06-24
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-06-25 deposited with the CCDC.
2018-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                103.335(5)
_cell_angle_beta                 105.575(6)
_cell_angle_gamma                108.689(6)
_cell_formula_units_Z            2
_cell_length_a                   10.8776(8)
_cell_length_b                   12.2628(8)
_cell_length_c                   15.8498(8)
_cell_measurement_reflns_used    3113
_cell_measurement_temperature    143.00(10)
_cell_measurement_theta_max      26.0100
_cell_measurement_theta_min      3.3370
_cell_volume                     1809.3(2)
_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
;
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 0.997
_diffrn_measured_fraction_theta_max 0.832
_diffrn_measurement_details
;
  1 omega    0.00   84.00   0.8000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   57.0000   30.0000 105

  2 omega   40.00   67.20   0.8000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   77.0000   60.0000 34

  3 omega  -31.00   45.00   0.8000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   57.0000  150.0000 95

  4 omega  -25.00   22.20   0.8000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000  150.0000 59

  5 omega   -8.00   23.20   0.8000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000   30.0000 39

  6 omega  -51.00   42.60   0.8000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -77.0000  -90.0000 117

  7 omega  -69.00  -34.60   0.8000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  178.0000   90.0000 43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0697719000
_diffrn_orient_matrix_UB_12      0.0050246000
_diffrn_orient_matrix_UB_13      0.0155276000
_diffrn_orient_matrix_UB_21      0.0063737000
_diffrn_orient_matrix_UB_22      0.0096625000
_diffrn_orient_matrix_UB_23      -0.0413395000
_diffrn_orient_matrix_UB_31      0.0242556000
_diffrn_orient_matrix_UB_32      0.0641901000
_diffrn_orient_matrix_UB_33      0.0224443000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.832
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16147
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.428
_diffrn_reflns_theta_min         2.968
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95834
_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 shiny crystal'
_exptl_crystal_density_diffrn    1.092
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             628
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         8322
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.1694
_refine_ls_R_factor_gt           0.0890
_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^)+(0.1593P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2484
_refine_ls_wR_factor_ref         0.3026
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3428
_reflns_number_total             8322
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qm00327k2.cif
_cod_data_source_block           160622_s2_yl_tizsq
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '507-509' was changed to
'508.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               1554227
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         c12h12n2o3
_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, All O(H) groups
2. Restrained distances
 C31-C32
 1.42 with sigma of 0.02
 C31A-C32A
 1.42 with sigma of 0.02
 C33-C32
 1.42 with sigma of 0.02
 C36A-C37A
 1.52 with sigma of 0.02
 C35A-C34A
 1.52 with sigma of 0.02
3. Restrained planarity
 C29A, C30A, C31A, C32A, C33A, C34A
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C33) = Uanis(C33A)
Uanis(C34) = Uanis(C34A)
Uanis(C35) = Uanis(C35A)
Uanis(C39) = Uanis(C39A)
Uanis(N2) = Uanis(N2A)
Uanis(C29) = Uanis(C29A)
Uanis(C31) = Uanis(C31A)
Uanis(C30) = Uanis(C30A)
Uanis(C32) = Uanis(C32A)
Uanis(C37) = Uanis(C36A)
Uanis(C36) = Uanis(C37A)
Uanis(C38) = Uanis(C38A)
5. Others
 Sof(C33A)=Sof(H33A)=Sof(C34A)=Sof(C35A)=Sof(H35A)=Sof(C39A)=Sof(H39A)=1-FVAR(1)
 Sof(C33)=Sof(H33)=Sof(C34)=Sof(C35)=Sof(H35)=Sof(C39)=Sof(H39)=FVAR(1)
 Sof(N2A)=1-FVAR(2)
 Sof(N2)=FVAR(2)
 Sof(C29A)=1-FVAR(3)
 Sof(C29)=FVAR(3)
 Sof(C30A)=Sof(H30A)=Sof(C31A)=Sof(H31A)=Sof(C32A)=Sof(H32A)=1-FVAR(4)
 Sof(C30)=Sof(H30)=Sof(C31)=Sof(H31)=Sof(C32)=Sof(H32)=FVAR(4)
 Sof(C36A)=Sof(H36C)=Sof(H36D)=1-FVAR(5)
 Sof(C37)=Sof(H37A)=Sof(H37B)=FVAR(5)
 Sof(C37A)=Sof(H37C)=Sof(H37D)=Sof(C38A)=Sof(H38C)=Sof(H38D)=1-FVAR(6)
 Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(C38)=Sof(H38A)=Sof(H38B)=FVAR(6)
6.a Ternary CH refined with riding coordinates:
 C8(H8), C12(H12), C35(H35), C39(H39), C35A(H35A), C39A(H39A)
6.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C36(H36A,H36B), C37(H37A,H37B),
 C38(H38A,H38B), C36A(H36C,H36D), C37A(H37C,H37D), C38A(H38C,H38D)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C5(H5), C6(H6), C14(H14), C16(H16), C17(H17), C25(H25),
 C27(H27), C30(H30), C31(H31), C32(H32), C33(H33), C30A(H30A), C31A(H31A),
 C32A(H32A), C33A(H33A)
6.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
6.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4)
;
_shelx_res_checksum              21792
_shelx_hkl_checksum              14726
_olex2_submission_special_instructions 'No special instructions were received'
_solvent_exptl_crystal_recrystallization_method dichloromethane/cyclohexane